Literature DB >> 35855367

Crystal-structure studies of 4-phenyl-piperazin-1-ium 4-eth-oxy-benzoate monohydrate, 4-phenyl-piperazin-1-ium 4-meth-oxy-benzoate monohydrate, 4-phenyl-piperazin-1-ium 4-methyl-benzoate monohydrate and 4-phenyl-piperazin-1-ium tri-fluoro-acetate 0.12-hydrate.

Ninganayaka Mahesha1, Haruvegowda Kiran Kumar1, Mehmet Akkurt2, Hemmige S Yathirajan1, Sabine Foro3, Mohammed S M Abdelbaky4, Santiago Garcia-Granda4.   

Abstract

In this study, four new piperazinium salts, namely, 4-phenyl-piperazin-1-ium 4-eth-oxy-benzoate monohydrate, C9H9O3·C10H15N2·H2O (I); 4-phenyl-piperazin-1-ium 4-meth-oxy-benzoate monohydrate, C10H15N2·C8H7O3·H2O (II); 4-phenyl-piperazin-1-ium 4-methyl-benzoate monohydrate, C10H15N2·C8H7O2·H2O (III); and 4-phenyl-piperazin-1-ium tri-fluoro-acetate 0.12 hydrate, C10H15N2·C2F3O2·0.12H2O (IV), have been synthesized. The single-crystal structures of these compounds reveal that all of them crystallize in the triclinic P space group and the crystal packing of (I)-(III) is built up of ribbons formed by a combination of hydrogen bonds of type N-H⋯O, O-H⋯O and other weak inter-actions of type C-H⋯O and C-H⋯π, leading to a three-dimensional network. In the crystal of (IV), the cations and the anions are connected by C-H⋯O, N-H⋯O and C-H⋯F hydrogen bonds and by C-H⋯π inter-actions, forming sheets which in turn inter-act to maintain the crystal structure by linking through the oxygen atoms of water mol-ecules and van der Waals inter-actions, giving the whole structure. © Mahesha et al. 2022.

Entities:  

Keywords:  biological activity; crystal structure; hydrogen bonding; piperazine

Year:  2022        PMID： 35855367      PMCID： PMC9260359          DOI： 10.1107/S2056989022006004

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Chemical context

Piperazines are among the most important building blocks in today’s drug discovery efforts and are found in biologically active compounds across a number of different therapeutic areas (Brockunier et al., 2004 ▸; Bogatcheva et al., 2006 ▸). For a review on the current pharmacological and toxicological information for piperazine derivative, see Elliott (2011 ▸). Various pharmacological properties of phenyl­piperazines and their derivatives have been discussed by several authors (Cohen et al., 1982 ▸; Conrado et al., 2010 ▸; Neves et al., 2003 ▸; Hanano et al., 2000 ▸). The design and synthesis of phenyl­piperazine derivatives as potent anti­cancer agents for prostate cancer have been described (Demirci et al., 2019 ▸). Many pharmaceutical compounds are derived from 1-phenyl­piperazine, viz., oxypertine, trazodone, nefazodone, etc. The crystal structures of 2-(4-methyl-2-phenyl­piperazin-4-ium-1-yl)pyridine-3-carboxyl­ate dehydrate (Li et al., 2008 ▸), 1-chloro-2-(4-phenyl­piperazin-1-yl)-ethanone (Xu & Jing, 2009 ▸), 4-phenyl­piperazin-1-ium di­hydrogen phosphate (Essid et al., 2010 ▸) and 1-phenyl­piperazine-1,4-diium bis­(hydrogen sulfate) (Marouani et al., 2010 ▸) have been reported, as have those of 4-phenyl­piperazin-1-ium 6-chloro-5-ethyl-2,4-dioxopyrimidin-1-ide and 4-phenyl­piperazin-1-ium 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide (Al-Alshaikh et al., 2015 ▸). We have reported the crystal structures of some salts of 4-meth­oxy­phenyl­piperazine (Kiran Kumar et al., 2019a ▸), six 1-aroyl-4-(4-meth­oxy­phen­yl)piperazines (Kiran Kumar et al., 2019b ▸), 2-meth­oxy­phenyl­piperazine (Harish Chinthal et al., 2020 ▸) and the recreational drug N-(4-meth­oxy­phen­yl)piperazine (MeOPP) and three of its salts (Kiran Kumar et al., 2020a ▸). In view of the importance of piperazines in general and the use of 1-phenyl­piperazine in particular, the present paper reports the crystal structure studies of some salts of 1-phenyl­piperazine with organic acids viz., 4-phenyl­piperazin-1-ium 4-eth­oxy­benzoate monohydrate, C9H9O3·C10H15N2·H2O (I); 4-phenyl­piperazin-1-ium 4-meth­oxy­benzoate monohydrate, C10H15N2·C8H7O3·H2O (II); 4-phenyl­piperazin-1-ium 4-methyl­benzoate monohydrate, C10H15N2·C8H7O2·H2O (III); and 4-phenyl­piperazin-1-ium tri­fluoro­acetate 0.12 hydrate C10H15N2·C2F3O2·0.12H2O (IV).

Structural commentary

The asymmetric unit of the compound (I), (Fig. 1 ▸), consists of a 4-phenyl­piperazin-1-ium cation, a 4-eth­oxy­benzoate anion and one water mol­ecule. The aromatic ring of the cation is essentially planar while the protonated piperazine ring adopts a chair conformation, with puckering parameters (Cremer & Pople, 1975 ▸) Q T = 0.553 (2) Å, θ = 175.0 (2)° and φ = 15 (3)°. In compound (II) the asymmetric unit (Fig. 2 ▸) comprises a 4-phenyl­piperazin-1-ium cation, a 4-meth­oxy­benzoate anion and one water mol­ecule. The aromatic ring of the cation is essentially planar while the protonated piperazine ring adopts a chair conformation, with puckering parameters Q T = 0.5614 (18) Å, θ = 175.89 (17)° and φ = 346 (3)°. Compound (III) presents an asymmetric unit (Fig. 3 ▸) composed of a 4-phenyl­piperazin-1-ium cation, a 4-methyl­benzoate anion and one water mol­ecule. The aromatic ring of the cation is essentially planar but the protonated piperazine ring adopts a distorted chair conformation, with puckering parameters Q T = 0.5486 (19) Å, θ = 9.38 (19)° and φ = 167.9 (13)°. On the other hand, the asymmetric unit of (IV) (Fig. 4 ▸) contains two 4-phenyl­piperazin-1-ium cations (A1 with N1, A2 with N3) and two tri­fluoro­acetate anions (B1 with F1, B2 with F4) and a 0.12 occupancy water molecule. The aromatic rings of the cations (A1, A2) are essentially planar while the protonated piperazine rings adopt a chair conformation for cation A1, with puckering parameters (Cremer & Pople, 1975 ▸) Q T = 0.552 (4) Å, θ = 0.0 (4)° and φ = 207 (14)°, and a distorted chair conformation for the cation A2, with puckering parameters Q T = 0.559 (5) Å, θ = 6.6 (4)° and φ = 168 (4)°.
Figure 1

The independent components of compound (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2

The independent components of compound (II) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 3

The independent components of compound (III) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 4

The independent components of compound (IV) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. (Atom splitting is omitted for clarity.)

Supra­molecular features

In the crystal structure of (I), the cation pairs are connected across two water mol­ecules by C—H⋯O and N—H⋯O hydrogen bonds, forming an (10) ring motif in which the anions and cations are linked through the water mol­ecules by O—H⋯O and N—H⋯O hydrogen bonds, forming ribbons along the a-axis direction (Table 1 ▸, Fig. 5 ▸ a). In addition, a set of C—H⋯π inter­actions, through the benzene rings of the anions and the cations, connect the mol­ecules together in ribbons along the a-axis direction (Table 1 ▸, Fig. 5 ▸ b). The C—H⋯O, N—H⋯O, O—H⋯O hydrogen bonds and C—H⋯π inter­actions together form a three-dimensional network, contributing to the stabilization of the crystal structure.
Table 1

Hydrogen-bond geometry (Å, °) for (I)

Cg1 and Cg3 are the centroids of the C12–C17 and C1–C6 benzene rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N2—HN1⋯OW1i 0.89 (2)1.94 (2)2.817 (3)167 (2)
N2—HN2⋯O10.93 (2)1.80 (2)2.724 (3)174 (2)
OW1—HW1⋯O20.88 (3)1.75 (3)2.630 (3)178 (4)
OW1—HW2⋯O1ii 0.91 (3)1.89 (3)2.789 (3)167 (3)
C9—H9A⋯OW10.972.523.308 (3)138
C1—H1⋯Cg1iii 0.932.913.607 (3)133
C5—H5⋯Cg1iv 0.932.793.570 (3)142
C18—H18B⋯Cg3v 0.972.883.737 (4)148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

Figure 5

Parts of the crystal structure of compound (I) showing (a) the formation of a cyclic hydrogen-bonded (10) aggregate and (b) a general view of C—H⋯π inter­actions parallel to [100]. Hydrogen bonds and C—H⋯π inter­actions are drawn as dashed lines.

In the crystal structure of (II), the cations, the anions and the water mol­ecules are connected by C—H⋯O, N—H⋯O and O—H⋯O hydrogen bonds, forming ribbons along the a-axis direction (Table 2 ▸, Fig. 6 ▸ a). Furthermore, the cations inter­act via C—-H⋯π inter­actions through the benzene ring of the anion, forming ribbons along the b-axis direction (Table 2 ▸, Fig. 6 ▸ b). The C—H⋯O, N—H⋯O, O—H⋯O hydrogen bonds and C—H⋯π inter­actions together form a three-dimensional network, contributing to the stabilization of the crystal structure.
Table 2

Hydrogen-bond geometry (Å, °) for (II)

Cg3 is the centroid of the C12–C17 benzene ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N2—HN1⋯OW1i 0.93 (2)1.91 (2)2.815 (2)166 (2)
OW1—HW1⋯O1ii 0.84 (2)1.80 (2)2.633 (2)175 (2)
N2—HN2⋯O20.93 (2)1.81 (2)2.7350 (19)176 (2)
OW1—HW2⋯O2iii 0.85 (2)1.96 (2)2.7876 (19)168 (2)
C8—H8B⋯OW1ii 0.972.533.331 (2)140
C1—H1⋯Cg3ii 0.932.763.549 (2)144
C5—H5⋯Cg3iv 0.932.863.625 (2)140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Figure 6

Parts of the crystal structure of compound (II) showing (a) the formation of hydrogen-bonded ribbons parallel to [010] and (b) a general view of the C—H⋯π inter­actions parallel to [010]. Hydrogen bonds and C—H⋯π inter­actions are drawn as dashed lines.

In the crystal structure of (III), the cations, the anions and the water mol­ecules are connected by C—H⋯O, N—H⋯O and O—H⋯O hydrogen bonds, forming ribbons along the a-axis direction (Table 3 ▸, Fig. 7 ▸). There are no C—H⋯π inter­actions or π-π stacking inter­actions. The crystal structure is stabilized by C—H⋯O, N—H⋯O, O—H⋯O hydrogen bonds and van der Waals inter­actions between the ribbons, which run along the a-axis direction.
Table 3

Hydrogen-bond geometry (Å, °) for (III)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
OW1—HW1⋯O2i 0.89 (3)1.90 (3)2.782 (2)171 (4)
OW1—HW2⋯O10.84 (2)1.92 (3)2.751 (2)172 (3)
N2—HN1⋯O1ii 0.90 (2)1.94 (2)2.819 (2)164 (2)
N2—HN2⋯O20.92 (2)1.80 (2)2.7207 (19)176 (2)
C8—H8A⋯OW10.972.333.116 (3)138

Symmetry codes: (i) ; (ii) .

Figure 7

Part of the crystal structure of compound (III) showing the formation of a hydrogen-bonded chain of rings parallel to [001]. Hydrogen bonds are drawn as dashed lines.

In the crystal structure of (IV), the cations and the anions are connected by C—H⋯O, N—H⋯O and C—H⋯F hydrogen bonds (Table 4 ▸, Fig. 8 ▸ a) and C—H⋯π inter­actions, generating sheets parallel to the (100) plane (Table 4 ▸, Fig. 8 ▸). These sheets further inter­act to maintain the crystal structure by linking through the oxygen atoms of water mol­ecules and by van der Waals inter­actions. As shown in Table 4 ▸, the main interactions in the structure of (IV) involve the oxygen atoms of carboxylate groups, while the 0.12 fraction of the water molecule contributes with one interaction of the type C—H⋯O and it is weak in comparison to the other oxygen-based ones.
Table 4

Hydrogen-bond geometry (Å, °) for (IV)

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N2—H21⋯O1i 0.881.912.790 (4)174
N2—H22⋯O30.872.042.860 (4)157
N2—H22⋯O40.872.473.164 (5)137
N4—H41⋯O4ii 0.861.952.759 (6)156
N4—H42⋯O2iii 0.891.902.758 (4)164
C18—H18A⋯F5′iii 0.972.533.273 (18)134
C18—H18B⋯Ow10.972.082.929 (15)145
C19—H19B⋯O3iv 0.972.593.420 (5)144
C20—H20A⋯F5iv 0.972.643.468 (8)144
C16—H16⋯Cg2v 0.932.993.745 (4)140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

Figure 8

Parts of the crystal structure of compound (IV) showing (a) a general view of the C—H⋯O, N—H⋯O and C—H⋯F hydrogen bonds and C—H⋯π inter­actions and (b) the mol­ecular packing of (IV) down the a-axis. Hydrogen bonds and C—H⋯π inter­actions are drawn as dashed lines.

Database survey

A search of the Cambridge Structural Database (Version 2020.3, last update February 2022; Groom et al., 2016 ▸) for an unsubstituted 4-phenyl­piperazin-1-ium cation and para-substituted benzoate anion involved in the reported salts (I)–(III) gave no hits. However, searching for a branched phenyl piperazinium cation and para-substituted benzoate anion gave comparable hits, namely; 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-fluoro­benzoate monohydrate, 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-chloro­benzoate monohydrate, 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-bromo­benzoate monohydrate (FOVPOY, FOVPUE, FOVQAL; Kiran Kumar et al., 2019a ▸), 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-iodo­benzoate monohydrate (KUJPUD; Kiran Kumar et al., 2020b ▸). They exhibit a meth­oxy group as a substituent in the 4-phenyl­piperazin-1-ium cation while the reported compounds (I)–(IV) have no substituent. They also crystallize as monohydrates, and their crystal structures are based on differently sized chains of rings formed via a combination of hydrogen bonds of the type N–H⋯O and O–H⋯O and other weak inter­actions of types C—H⋯O and C—H⋯π to form sheets. In 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-amino­benzoate monohydrate (IHIMEU; Kiran Kumar et al., 2020a ▸) the presence of the amino substituent in the anion, which acts as both a donor and as an acceptor of hydrogen bonds, makes the supra­molecular assembly of this compound more complex than those reported here. A search for 4-phenyl­piperazin-1-ium and acetate derivatives involved in the reported compound (IV) gave no hits.

Synthesis and crystallization

For the synthesis of salts (I)–(IV), a solution of commercially available (from Sigma–Aldrich) 1-phenyl­piperazine (100 mg, 0.62 mol) in methanol (10 ml) was mixed with equimolar solutions of the appropriate organic acids in methanol (10 ml) viz., 4-eth­oxy­benzoic acid (103 mg, 0.62 mol) for (I), 4-meth­oxy­benzoic acid (94 mg, 0.62 mol) for (II), 4-methyl­benzoic acid (84 mg, 0.62 mol) for (III) and tri­fluoro­acetic acid (71 mg, 0.62 mol) for (IV). The corresponding solutions were stirred for 15 min at room temperature and allowed to stand at the same temperature. X-ray quality crystals were formed on slow evaporation in a week for all compounds, where ethanol:ethyl­acetate (1:1) was used for crystallization. The corresponding melting points were 353–355 K for (I), 368–370 K for (II), 338–340 K for (III) and 385–387 K for (IV).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5 ▸. All H atoms bonded to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), C—H = 0.96 Å (meth­yl) or 0.97 Å (methyl­ene), with U iso(H) = 1.2U eq(C) or 1.5U eq(C). For the H atoms bonded to the N and O atoms, the atomic coordinates were refined with U iso(H) = 1.2U eq(N) and 1.5U eq(O), [for (I), N2—HN2 = 0.931 (19), N2—HN1 = 0.888 (17) Å and OW1—HW2 = 0.91 (3), OW1—HW1 = 0.88 (3) Å; for (II), N2—HN1 = 0.927 (16), N2—HN2 = 0.931 (18) Å and OW—HW1 = 0.840 (19), OW1—HW2 = 0.85 (2) Å; for (III), N2—HN1 = 0.900 (16), N2—HN2 = 0.918 (17) Å and OW1—HW1 = 0.89 (3), OW1—HW2 = 0.84 (2) Å and for (IV), N2—H22 = 0.87 (2) and N2—H21 = 0.88 (3) Å]. In (IV), the atoms of the CF3 groups of two tri­fluoro­acetate anions (B1, B2) are disordered over two sets of sites with site occupancies of 0.737 (3) and 0.263 (3). The corresponding bond distances in the disordered groups were restrained to be equal. The U ij components of these atoms were restrained to be equal and were restrained to approximate isotropic behaviour. The OW1 water molecule was refined with a resulting occupation factor of 0.245 (10) and the H atoms of the water molecule were placed geometrically.
Table 5

Experimental details

 (I)(II)(III)(IV)
Crystal data
Chemical formulaC10H15N2 +·C9H9O3 −·H2OC10H15N2 +·C8H7O3 −·H2OC10H15N2 +·C8H7O2 −·H2OC10H15N2 +·C2F3O2 −·0.123H2O
M r 346.42332.39316.39278.47
Crystal system, space groupTriclinic, P Triclinic, P Triclinic, P Triclinic, P
Temperature (K)293293293293
a, b, c (Å)6.1635 (5), 7.5946 (6), 20.458 (2)6.2039 (4), 7.5565 (7), 18.614 (1)6.1175 (5), 7.6225 (7), 18.452 (1)9.6544 (6), 9.9029 (6), 15.2090 (9)
α, β, γ (°)79.545 (7), 86.521 (7), 83.791 (7)81.799 (7), 87.020 (7), 84.852 (7)97.421 (9), 90.403 (8), 92.405 (8)79.621 (6), 86.579 (6), 70.603 (6)
V (Å3)935.38 (14)859.53 (11)852.40 (12)1349.10 (15)
Z 2224
Radiation typeMo KαMo KαMo KαMo Kα
μ (mm−1)0.090.090.080.12
Crystal size (mm)0.48 × 0.42 × 0.10.48 × 0.48 × 0.320.5 × 0.4 × 0.080.48 × 0.48 × 0.36
 
Data collection
DiffractometerOxford Diffraction XcaliburOxford Diffraction XcaliburOxford Diffraction XcaliburOxford Diffraction Xcalibur
Absorption correctionMulti-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)Multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▸)
T min, T max 0.623, 1.0000.520, 1.0000.837, 1.0000.724, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections5989, 3429, 21595360, 3142, 23225354, 3126, 22489220, 4940, 2777
R int 0.0220.0160.0130.014
(sin θ/λ)max (Å−1)0.6020.6020.6020.602
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.054, 0.124, 1.080.045, 0.125, 1.060.046, 0.128, 1.030.070, 0.235, 1.07
No. of reflections3424313931184927
No. of parameters244230226375
No. of restraints2444
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.15, −0.150.2, −0.170.16, −0.160.42, −0.28

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009 ▸), CrysAlis RED (Oxford Diffraction, 2009 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2014 (Sheldrick, 2015b ▸), Mercury (Macrae et al., 2020 ▸), PLATON (Spek, 2020 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) global, I, II, III, IV. DOI: 10.1107/S2056989022006004/dj2048sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989022006004/dj2048Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989022006004/dj2048Isup6.cml Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989022006004/dj2048IIsup3.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989022006004/dj2048IIsup7.cml Structure factors: contains datablock(s) III. DOI: 10.1107/S2056989022006004/dj2048IIIsup4.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989022006004/dj2048IIIsup8.cml Structure factors: contains datablock(s) IV. DOI: 10.1107/S2056989022006004/dj2048IVsup5.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989022006004/dj2048IVsup9.cml CCDC references: 2177037, 2177036, 2177035, 2177034 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H15N2+·C9H9O3−·H2OZ = 2
Mr = 346.42F(000) = 372
Triclinic, P1Dx = 1.23 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.1635 (5) ÅCell parameters from 2352 reflections
b = 7.5946 (6) Åθ = 3.0–27.8°
c = 20.458 (2) ŵ = 0.09 mm−1
α = 79.545 (7)°T = 293 K
β = 86.521 (7)°Plate, colourless
γ = 83.791 (7)°0.48 × 0.42 × 0.1 mm
V = 935.38 (14) Å3
Oxford Diffraction Xcalibur diffractometer2159 reflections with I > 2σ(I)
ω scansRint = 0.022
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)θmax = 25.4°, θmin = 3.0°
Tmin = 0.623, Tmax = 1.000h = −7→7
5989 measured reflectionsk = −9→9
3429 independent reflectionsl = −24→14
Refinement on F2Secondary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124w = 1/[σ2(Fo2) + (0.0392P)2 + 0.2859P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
3424 reflectionsΔρmax = 0.15 e Å−3
244 parametersΔρmin = −0.15 e Å−3
2 restraintsExtinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0058 (17)
Primary atom site location: structure-invariant direct methods
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
xyzUiso*/Ueq
C10.1990 (4)0.7508 (4)0.79338 (12)0.0626 (7)
H10.0692520.8099890.7761250.075*
C20.2437 (5)0.7539 (4)0.85869 (13)0.0782 (9)
H20.1428530.8142950.8846410.094*
C30.4331 (5)0.6699 (4)0.88559 (14)0.0759 (9)
H30.4621630.6720730.9295040.091*
C40.5786 (5)0.5827 (4)0.84658 (14)0.0753 (8)
H40.7090950.5259990.8640830.09*
C50.5363 (4)0.5771 (3)0.78183 (12)0.0579 (7)
H50.6381060.5158370.7564450.069*
C60.3432 (3)0.6615 (3)0.75355 (10)0.0407 (5)
C70.1046 (3)0.7635 (3)0.66062 (11)0.0484 (6)
H7A0.1306630.8887330.6567710.058*
H7B−0.019690.7421380.6913980.058*
C80.0502 (3)0.7292 (3)0.59343 (11)0.0496 (6)
H8A0.0050850.6090010.597980.059*
H8B−0.070320.8144580.5761450.059*
C90.4290 (3)0.6216 (3)0.57366 (10)0.0480 (6)
H9A0.5550620.6348350.5430530.058*
H9B0.3923610.4987130.5786250.058*
C100.4839 (3)0.6594 (3)0.64012 (10)0.0447 (6)
H10A0.6026150.5729850.6579580.054*
H10B0.53330.7784580.6341860.054*
C110.2356 (4)0.7988 (3)0.37750 (13)0.0504 (6)
C120.1740 (3)0.8093 (3)0.30715 (11)0.0409 (5)
C13−0.0108 (3)0.7381 (3)0.29259 (11)0.0462 (6)
H13−0.099870.6850180.3273260.055*
C14−0.0669 (4)0.7436 (3)0.22762 (11)0.0496 (6)
H14−0.1917240.6943490.2189880.06*
C150.0633 (4)0.8223 (3)0.17610 (11)0.0480 (6)
C160.2462 (4)0.8988 (3)0.18948 (12)0.0547 (6)
H160.3322640.9550740.1546490.066*
C170.3005 (4)0.8916 (3)0.25403 (12)0.0521 (6)
H170.4241780.9426780.2624210.063*
C18−0.1614 (5)0.7562 (5)0.09410 (14)0.0931 (10)
H18A−0.2938050.8183590.1103770.112*
H18B−0.1552910.630230.1146070.112*
C19−0.1605 (8)0.7747 (7)0.02032 (17)0.178 (2)
H19A−0.1958230.8987670.001010.268*
H19B−0.2668710.7037960.0084940.268*
H19C−0.0182880.733640.0039150.268*
N10.2969 (3)0.6493 (2)0.68767 (8)0.0382 (4)
N20.2420 (3)0.7474 (3)0.54621 (10)0.0452 (5)
O10.1211 (3)0.7133 (2)0.42359 (8)0.0622 (5)
O20.3970 (3)0.8727 (3)0.38724 (10)0.0885 (7)
O30.0253 (3)0.8330 (2)0.11014 (8)0.0681 (5)
OW10.7230 (4)0.8819 (2)0.46338 (9)0.0591 (5)
HN10.275 (4)0.860 (2)0.5421 (11)0.056 (7)*
HN20.208 (4)0.729 (3)0.5044 (9)0.067 (8)*
HW10.612 (5)0.879 (4)0.4385 (15)0.102 (11)*
HW20.842 (5)0.825 (4)0.4445 (15)0.102 (12)*
U11U22U33U12U13U23
C10.0719 (17)0.0673 (18)0.0465 (15)0.0151 (14)−0.0066 (13)−0.0156 (13)
C20.103 (2)0.079 (2)0.0522 (17)0.0150 (18)−0.0020 (16)−0.0248 (15)
C30.106 (2)0.076 (2)0.0510 (17)−0.0055 (18)−0.0223 (17)−0.0207 (15)
C40.0735 (18)0.090 (2)0.0636 (18)0.0027 (16)−0.0267 (15)−0.0145 (17)
C50.0561 (15)0.0696 (18)0.0486 (15)0.0031 (13)−0.0116 (12)−0.0147 (13)
C60.0467 (12)0.0353 (13)0.0414 (13)−0.0092 (10)−0.0045 (10)−0.0067 (10)
C70.0399 (12)0.0595 (16)0.0441 (13)0.0007 (11)−0.0025 (10)−0.0078 (11)
C80.0407 (12)0.0622 (16)0.0445 (14)−0.0045 (11)−0.0053 (10)−0.0053 (11)
C90.0480 (13)0.0512 (15)0.0423 (13)−0.0011 (11)0.0026 (10)−0.0057 (11)
C100.0396 (12)0.0496 (14)0.0435 (13)−0.0024 (10)−0.0018 (10)−0.0062 (11)
C110.0524 (14)0.0427 (14)0.0593 (17)0.0050 (12)−0.0162 (13)−0.0190 (12)
C120.0398 (12)0.0373 (13)0.0475 (13)−0.0007 (10)−0.0072 (10)−0.0121 (10)
C130.0494 (13)0.0462 (14)0.0432 (13)−0.0111 (11)−0.0024 (11)−0.0048 (11)
C140.0502 (13)0.0519 (15)0.0490 (14)−0.0163 (11)−0.0091 (11)−0.0063 (12)
C150.0556 (14)0.0469 (15)0.0412 (14)−0.0042 (11)−0.0052 (11)−0.0065 (11)
C160.0534 (14)0.0566 (16)0.0533 (16)−0.0136 (12)0.0088 (12)−0.0063 (12)
C170.0409 (12)0.0533 (16)0.0659 (17)−0.0098 (11)−0.0026 (12)−0.0174 (13)
C180.111 (2)0.121 (3)0.0572 (18)−0.046 (2)−0.0218 (17)−0.0148 (18)
C190.242 (6)0.251 (6)0.063 (2)−0.137 (5)−0.039 (3)−0.007 (3)
N10.0374 (9)0.0419 (11)0.0350 (10)−0.0028 (8)−0.0021 (8)−0.0062 (8)
N20.0548 (12)0.0428 (13)0.0390 (11)−0.0088 (10)−0.0079 (9)−0.0058 (9)
O10.0706 (11)0.0703 (12)0.0465 (10)−0.0048 (10)−0.0127 (9)−0.0108 (9)
O20.0835 (13)0.1109 (17)0.0825 (14)−0.0368 (12)−0.0321 (11)−0.0215 (12)
O30.0816 (12)0.0792 (13)0.0450 (10)−0.0182 (10)−0.0052 (9)−0.0080 (9)
OW10.0593 (11)0.0598 (12)0.0604 (12)−0.0122 (10)−0.0135 (10)−0.0092 (9)
C1—C61.377 (3)C11—O21.237 (3)
C1—C21.385 (3)C11—O11.267 (3)
C1—H10.93C11—C121.497 (3)
C2—C31.365 (4)C12—C131.383 (3)
C2—H20.93C12—C171.391 (3)
C3—C41.362 (4)C13—C141.386 (3)
C3—H30.93C13—H130.93
C4—C51.375 (3)C14—C151.373 (3)
C4—H40.93C14—H140.93
C5—C61.395 (3)C15—O31.370 (3)
C5—H50.93C15—C161.386 (3)
C6—N11.416 (3)C16—C171.372 (3)
C7—N11.465 (2)C16—H160.93
C7—C81.508 (3)C17—H170.93
C7—H7A0.97C18—O31.425 (3)
C7—H7B0.97C18—C191.490 (4)
C8—N21.482 (3)C18—H18A0.97
C8—H8A0.97C18—H18B0.97
C8—H8B0.97C19—H19A0.96
C9—N21.484 (3)C19—H19B0.96
C9—C101.504 (3)C19—H19C0.96
C9—H9A0.97N2—HN10.887 (16)
C9—H9B0.97N2—HN20.930 (16)
C10—N11.462 (3)OW1—HW10.88 (3)
C10—H10A0.97OW1—HW20.91 (3)
C10—H10B0.97
C6—C1—C2121.2 (2)O2—C11—C12118.0 (2)
C6—C1—H1119.4O1—C11—C12118.2 (2)
C2—C1—H1119.4C13—C12—C17117.6 (2)
C3—C2—C1121.1 (3)C13—C12—C11121.3 (2)
C3—C2—H2119.4C17—C12—C11121.1 (2)
C1—C2—H2119.4C12—C13—C14121.8 (2)
C4—C3—C2118.4 (3)C12—C13—H13119.1
C4—C3—H3120.8C14—C13—H13119.1
C2—C3—H3120.8C15—C14—C13119.4 (2)
C3—C4—C5121.3 (3)C15—C14—H14120.3
C3—C4—H4119.4C13—C14—H14120.3
C5—C4—H4119.4O3—C15—C14124.4 (2)
C4—C5—C6121.1 (2)O3—C15—C16115.8 (2)
C4—C5—H5119.4C14—C15—C16119.8 (2)
C6—C5—H5119.4C17—C16—C15120.1 (2)
C1—C6—C5116.9 (2)C17—C16—H16119.9
C1—C6—N1122.23 (19)C15—C16—H16119.9
C5—C6—N1120.8 (2)C16—C17—C12121.2 (2)
N1—C7—C8112.74 (18)C16—C17—H17119.4
N1—C7—H7A109C12—C17—H17119.4
C8—C7—H7A109O3—C18—C19107.7 (3)
N1—C7—H7B109O3—C18—H18A110.2
C8—C7—H7B109C19—C18—H18A110.2
H7A—C7—H7B107.8O3—C18—H18B110.2
N2—C8—C7110.70 (17)C19—C18—H18B110.2
N2—C8—H8A109.5H18A—C18—H18B108.5
C7—C8—H8A109.5C18—C19—H19A109.5
N2—C8—H8B109.5C18—C19—H19B109.5
C7—C8—H8B109.5H19A—C19—H19B109.5
H8A—C8—H8B108.1C18—C19—H19C109.5
N2—C9—C10110.47 (18)H19A—C19—H19C109.5
N2—C9—H9A109.6H19B—C19—H19C109.5
C10—C9—H9A109.6C6—N1—C10115.21 (16)
N2—C9—H9B109.6C6—N1—C7115.50 (17)
C10—C9—H9B109.6C10—N1—C7111.72 (16)
H9A—C9—H9B108.1C8—N2—C9109.60 (17)
N1—C10—C9112.16 (17)C8—N2—HN1106.9 (15)
N1—C10—H10A109.2C9—N2—HN1109.4 (15)
C9—C10—H10A109.2C8—N2—HN2110.8 (15)
N1—C10—H10B109.2C9—N2—HN2112.2 (15)
C9—C10—H10B109.2HN1—N2—HN2108 (2)
H10A—C10—H10B107.9C15—O3—C18117.7 (2)
O2—C11—O1123.7 (2)HW1—OW1—HW2107 (3)
C6—C1—C2—C30.6 (4)O3—C15—C16—C17−178.7 (2)
C1—C2—C3—C40.2 (5)C14—C15—C16—C171.8 (4)
C2—C3—C4—C5−0.7 (5)C15—C16—C17—C12−0.4 (4)
C3—C4—C5—C60.5 (4)C13—C12—C17—C16−1.2 (3)
C2—C1—C6—C5−0.8 (4)C11—C12—C17—C16178.9 (2)
C2—C1—C6—N1177.0 (2)C1—C6—N1—C10143.0 (2)
C4—C5—C6—C10.3 (4)C5—C6—N1—C10−39.3 (3)
C4—C5—C6—N1−177.6 (2)C1—C6—N1—C710.3 (3)
N1—C7—C8—N2−54.6 (3)C5—C6—N1—C7−171.9 (2)
N2—C9—C10—N156.7 (2)C9—C10—N1—C6172.59 (17)
O2—C11—C12—C13−176.6 (2)C9—C10—N1—C7−53.0 (2)
O1—C11—C12—C134.1 (3)C8—C7—N1—C6−173.71 (18)
O2—C11—C12—C173.3 (3)C8—C7—N1—C1052.0 (2)
O1—C11—C12—C17−176.0 (2)C7—C8—N2—C957.2 (2)
C17—C12—C13—C141.6 (3)C10—C9—N2—C8−58.4 (2)
C11—C12—C13—C14−178.6 (2)C14—C15—O3—C18−0.4 (4)
C12—C13—C14—C15−0.3 (3)C16—C15—O3—C18−179.9 (2)
C13—C14—C15—O3179.1 (2)C19—C18—O3—C15−176.7 (3)
C13—C14—C15—C16−1.4 (3)
D—H···AD—HH···AD···AD—H···A
N2—HN1···OW1i0.89 (2)1.94 (2)2.817 (3)167 (2)
N2—HN2···O10.93 (2)1.80 (2)2.724 (3)174 (2)
OW1—HW1···O20.88 (3)1.75 (3)2.630 (3)178 (4)
OW1—HW2···O1ii0.91 (3)1.89 (3)2.789 (3)167 (3)
C9—H9A···OW10.972.523.308 (3)138
C1—H1···Cg1iii0.932.913.607 (3)133
C5—H5···Cg1iv0.932.793.570 (3)142
C18—H18B···Cg3v0.972.883.737 (4)148
C10H15N2+·C8H7O3−·H2OZ = 2
Mr = 332.39F(000) = 356
Triclinic, P1Dx = 1.284 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2039 (4) ÅCell parameters from 2855 reflections
b = 7.5565 (7) Åθ = 3.1–27.8°
c = 18.614 (1) ŵ = 0.09 mm−1
α = 81.799 (7)°T = 293 K
β = 87.020 (7)°Prism, colourless
γ = 84.852 (7)°0.48 × 0.48 × 0.32 mm
V = 859.53 (11) Å3
Oxford Diffraction Xcalibur diffractometer2322 reflections with I > 2σ(I)
ω scansRint = 0.016
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)θmax = 25.3°, θmin = 3.1°
Tmin = 0.520, Tmax = 1.000h = −7→5
5360 measured reflectionsk = −9→9
3142 independent reflectionsl = −22→22
Refinement on F2Secondary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125w = 1/[σ2(Fo2) + (0.0613P)2 + 0.1503P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3139 reflectionsΔρmax = 0.2 e Å−3
230 parametersΔρmin = −0.16 e Å−3
4 restraintsExtinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.032 (4)
Primary atom site location: structure-invariant direct methods
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
xyzUiso*/Ueq
C1−0.0254 (3)0.4086 (3)0.19209 (10)0.0516 (5)
H1−0.1208580.4763820.2196290.062*
C2−0.0695 (3)0.3996 (3)0.12102 (11)0.0625 (6)
H2−0.1948980.460270.1015330.075*
C30.0686 (3)0.3024 (3)0.07854 (10)0.0597 (6)
H30.0399570.2984020.0302790.072*
C40.2497 (3)0.2117 (3)0.10901 (10)0.0593 (6)
H40.3437020.1439090.081020.071*
C50.2964 (3)0.2181 (3)0.18024 (9)0.0512 (5)
H50.4207320.1549120.1994330.061*
C60.1594 (2)0.3180 (2)0.22353 (8)0.0361 (4)
C70.0222 (3)0.3258 (2)0.34797 (8)0.0419 (4)
H7A−0.0264610.2059150.3543190.05*
H7B−0.0960840.409060.328890.05*
C80.0795 (3)0.3708 (2)0.42029 (9)0.0456 (4)
H8A0.1168890.4940940.4148580.055*
H8B−0.0445310.3593570.4540530.055*
C90.4547 (3)0.2652 (3)0.39777 (9)0.0485 (5)
H9A0.5745980.1829670.4163360.058*
H9B0.4996610.3861460.3927340.058*
C100.3979 (3)0.2229 (3)0.32457 (9)0.0445 (4)
H10A0.5205810.2412830.290680.053*
H10B0.369280.0976550.3289480.053*
C110.2655 (3)0.2146 (2)0.63263 (10)0.0474 (5)
C120.3208 (3)0.2073 (2)0.71052 (9)0.0389 (4)
C130.1897 (3)0.1251 (2)0.76647 (10)0.0479 (5)
H130.0678290.0727330.7552730.057*
C140.2386 (3)0.1207 (3)0.83782 (10)0.0496 (5)
H140.1498750.0651780.8744610.06*
C150.4186 (3)0.1982 (2)0.85567 (9)0.0442 (4)
C160.5528 (3)0.2784 (2)0.80102 (9)0.0453 (4)
H160.6751830.3297130.8123490.054*
C170.5021 (3)0.2808 (2)0.72949 (9)0.0424 (4)
H170.5929940.3337660.69290.051*
C180.6395 (4)0.2628 (4)0.94845 (12)0.0858 (8)
H13A0.6438150.2483031.0004490.129*
H13B0.766630.2014650.9289510.129*
H13C0.634550.3881250.9296160.129*
N10.2079 (2)0.33487 (18)0.29565 (7)0.0359 (3)
N20.2652 (2)0.2489 (2)0.44963 (8)0.0434 (4)
O10.1058 (3)0.1395 (3)0.61995 (9)0.0873 (6)
O20.3847 (2)0.29717 (19)0.58441 (7)0.0598 (4)
O30.4517 (2)0.1895 (2)0.92816 (7)0.0620 (4)
OW10.2271 (2)0.8777 (2)0.46022 (8)0.0579 (4)
HN10.230 (3)0.131 (2)0.4565 (11)0.07*
HW10.120 (3)0.865 (3)0.4356 (11)0.07*
HN20.303 (3)0.270 (3)0.4956 (9)0.07*
HW20.336 (3)0.822 (3)0.4413 (12)0.07*
U11U22U33U12U13U23
C10.0534 (11)0.0579 (12)0.0441 (10)0.0127 (9)−0.0106 (8)−0.0169 (9)
C20.0654 (13)0.0739 (14)0.0491 (11)0.0143 (11)−0.0228 (10)−0.0166 (10)
C30.0820 (14)0.0654 (13)0.0347 (10)−0.0036 (11)−0.0147 (10)−0.0145 (9)
C40.0717 (13)0.0660 (13)0.0411 (10)0.0070 (11)0.0022 (9)−0.0202 (9)
C50.0535 (11)0.0597 (12)0.0399 (10)0.0105 (9)−0.0032 (8)−0.0137 (8)
C60.0405 (9)0.0344 (9)0.0346 (8)−0.0042 (7)−0.0035 (7)−0.0071 (7)
C70.0388 (9)0.0515 (11)0.0352 (9)0.0009 (8)−0.0006 (7)−0.0083 (7)
C80.0518 (10)0.0495 (11)0.0354 (9)0.0016 (8)0.0004 (8)−0.0104 (8)
C90.0425 (10)0.0619 (12)0.0419 (10)−0.0015 (8)−0.0105 (8)−0.0090 (8)
C100.0385 (9)0.0569 (11)0.0381 (9)0.0049 (8)−0.0053 (7)−0.0113 (8)
C110.0484 (11)0.0464 (11)0.0508 (11)0.0051 (8)−0.0161 (9)−0.0190 (9)
C120.0387 (9)0.0356 (9)0.0443 (9)0.0023 (7)−0.0086 (7)−0.0131 (7)
C130.0366 (9)0.0485 (11)0.0617 (12)−0.0058 (8)−0.0057 (8)−0.0157 (9)
C140.0437 (10)0.0551 (12)0.0500 (11)−0.0060 (8)0.0047 (8)−0.0079 (9)
C150.0450 (10)0.0485 (10)0.0398 (9)0.0020 (8)−0.0042 (8)−0.0110 (8)
C160.0461 (10)0.0501 (11)0.0430 (10)−0.0103 (8)−0.0101 (8)−0.0112 (8)
C170.0447 (10)0.0437 (10)0.0400 (9)−0.0072 (8)−0.0036 (7)−0.0075 (7)
C180.0785 (16)0.136 (2)0.0509 (13)−0.0228 (16)−0.0171 (11)−0.0274 (14)
N10.0347 (7)0.0416 (8)0.0320 (7)0.0006 (6)−0.0034 (5)−0.0091 (6)
N20.0553 (9)0.0450 (8)0.0319 (7)−0.0061 (7)−0.0089 (6)−0.0082 (6)
O10.0815 (11)0.1184 (15)0.0727 (11)−0.0352 (10)−0.0327 (9)−0.0230 (10)
O20.0721 (9)0.0700 (10)0.0402 (7)−0.0038 (7)−0.0139 (7)−0.0144 (7)
O30.0641 (9)0.0866 (11)0.0365 (7)−0.0067 (8)−0.0047 (6)−0.0117 (7)
OW10.0595 (9)0.0631 (9)0.0544 (8)−0.0097 (7)−0.0177 (7)−0.0108 (7)
C1—C21.377 (3)C10—H10A0.97
C1—C61.393 (2)C10—H10B0.97
C1—H10.93C11—O11.234 (2)
C2—C31.371 (3)C11—O21.263 (2)
C2—H20.93C11—C121.499 (2)
C3—C41.368 (3)C12—C171.381 (2)
C3—H30.93C12—C131.396 (3)
C4—C51.380 (3)C13—C141.373 (3)
C4—H40.93C13—H130.93
C5—C61.388 (2)C14—C151.383 (3)
C5—H50.93C14—H140.93
C6—N11.4165 (19)C15—O31.367 (2)
C7—N11.469 (2)C15—C161.386 (2)
C7—C81.502 (2)C16—C171.381 (2)
C7—H7A0.97C16—H160.93
C7—H7B0.97C17—H170.93
C8—N21.485 (2)C18—O31.424 (3)
C8—H8A0.97C18—H13A0.96
C8—H8B0.97C18—H13B0.96
C9—N21.484 (2)C18—H13C0.96
C9—C101.509 (2)N2—HN10.924 (15)
C9—H9A0.97N2—HN20.938 (16)
C9—H9B0.97OW1—HW10.847 (16)
C10—N11.467 (2)OW1—HW20.850 (16)
C2—C1—C6121.26 (16)C9—C10—H10B109.1
C2—C1—H1119.4H10A—C10—H10B107.9
C6—C1—H1119.4O1—C11—O2124.33 (18)
C3—C2—C1121.01 (18)O1—C11—C12117.62 (19)
C3—C2—H2119.5O2—C11—C12118.06 (16)
C1—C2—H2119.5C17—C12—C13117.75 (16)
C4—C3—C2118.25 (17)C17—C12—C11121.49 (16)
C4—C3—H3120.9C13—C12—C11120.77 (16)
C2—C3—H3120.9C14—C13—C12120.75 (16)
C3—C4—C5121.67 (17)C14—C13—H13119.6
C3—C4—H4119.2C12—C13—H13119.6
C5—C4—H4119.2C13—C14—C15120.56 (17)
C4—C5—C6120.65 (17)C13—C14—H14119.7
C4—C5—H5119.7C15—C14—H14119.7
C6—C5—H5119.7O3—C15—C14116.20 (16)
C5—C6—C1117.15 (15)O3—C15—C16124.10 (16)
C5—C6—N1122.11 (14)C14—C15—C16119.69 (16)
C1—C6—N1120.68 (14)C17—C16—C15119.06 (16)
N1—C7—C8111.59 (14)C17—C16—H16120.5
N1—C7—H7A109.3C15—C16—H16120.5
C8—C7—H7A109.3C16—C17—C12122.16 (16)
N1—C7—H7B109.3C16—C17—H17118.9
C8—C7—H7B109.3C12—C17—H17118.9
H7A—C7—H7B108O3—C18—H13A109.5
N2—C8—C7110.40 (13)O3—C18—H13B109.5
N2—C8—H8A109.6H13A—C18—H13B109.5
C7—C8—H8A109.6O3—C18—H13C109.5
N2—C8—H8B109.6H13A—C18—H13C109.5
C7—C8—H8B109.6H13B—C18—H13C109.5
H8A—C8—H8B108.1C6—N1—C10115.62 (12)
N2—C9—C10110.34 (14)C6—N1—C7114.90 (12)
N2—C9—H9A109.6C10—N1—C7111.53 (12)
C10—C9—H9A109.6C9—N2—C8109.67 (13)
N2—C9—H9B109.6C9—N2—HN1108.7 (13)
C10—C9—H9B109.6C8—N2—HN1110.6 (13)
H9A—C9—H9B108.1C9—N2—HN2110.0 (13)
N1—C10—C9112.30 (13)C8—N2—HN2113.2 (13)
N1—C10—H10A109.1HN1—N2—HN2104.5 (18)
C9—C10—H10A109.1C15—O3—C18117.68 (16)
N1—C10—H10B109.1HW1—OW1—HW2106 (2)
C6—C1—C2—C3−0.7 (3)C13—C14—C15—C16−1.1 (3)
C1—C2—C3—C41.2 (3)O3—C15—C16—C17−179.35 (16)
C2—C3—C4—C5−0.9 (3)C14—C15—C16—C170.7 (3)
C3—C4—C5—C60.0 (3)C15—C16—C17—C120.5 (3)
C4—C5—C6—C10.6 (3)C13—C12—C17—C16−1.4 (2)
C4—C5—C6—N1−176.76 (18)C11—C12—C17—C16178.68 (15)
C2—C1—C6—C5−0.2 (3)C5—C6—N1—C10−7.1 (2)
C2—C1—C6—N1177.14 (18)C1—C6—N1—C10175.65 (16)
N1—C7—C8—N2−57.13 (19)C5—C6—N1—C7−139.28 (17)
N2—C9—C10—N155.4 (2)C1—C6—N1—C743.5 (2)
O1—C11—C12—C17177.14 (17)C9—C10—N1—C6172.93 (14)
O2—C11—C12—C17−3.0 (2)C9—C10—N1—C7−53.34 (19)
O1—C11—C12—C13−2.8 (2)C8—C7—N1—C6−171.86 (13)
O2—C11—C12—C13177.07 (16)C8—C7—N1—C1054.06 (18)
C17—C12—C13—C141.0 (2)C10—C9—N2—C8−57.61 (19)
C11—C12—C13—C14−179.05 (15)C7—C8—N2—C958.76 (19)
C12—C13—C14—C150.2 (3)C14—C15—O3—C18178.00 (19)
C13—C14—C15—O3178.99 (15)C16—C15—O3—C18−1.9 (3)
D—H···AD—HH···AD···AD—H···A
N2—HN1···OW1i0.93 (2)1.91 (2)2.815 (2)166 (2)
OW1—HW1···O1ii0.84 (2)1.80 (2)2.633 (2)175 (2)
N2—HN2···O20.93 (2)1.81 (2)2.7350 (19)176 (2)
OW1—HW2···O2iii0.85 (2)1.96 (2)2.7876 (19)168 (2)
C8—H8B···OW1ii0.972.533.331 (2)140
C1—H1···Cg3ii0.932.763.549 (2)144
C5—H5···Cg3iv0.932.863.625 (2)140
C10H15N2+·C8H7O2−·H2OZ = 2
Mr = 316.39F(000) = 340
Triclinic, P1Dx = 1.233 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.1175 (5) ÅCell parameters from 2877 reflections
b = 7.6225 (7) Åθ = 3.0–27.8°
c = 18.452 (1) ŵ = 0.08 mm−1
α = 97.421 (9)°T = 293 K
β = 90.403 (8)°Plate, colourless
γ = 92.405 (8)°0.5 × 0.4 × 0.08 mm
V = 852.40 (12) Å3
Oxford Diffraction Xcalibur diffractometer2248 reflections with I > 2σ(I)
ω scansRint = 0.013
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)θmax = 25.4°, θmin = 3.1°
Tmin = 0.837, Tmax = 1.000h = −7→7
5354 measured reflectionsk = −7→9
3126 independent reflectionsl = −22→22
Refinement on F2Secondary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128w = 1/[σ2(Fo2) + (0.0582P)2 + 0.2086P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3118 reflectionsΔρmax = 0.16 e Å−3
226 parametersΔρmin = −0.16 e Å−3
4 restraintsExtinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.011 (3)
Primary atom site location: structure-invariant direct methods
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
xyzUiso*/Ueq
C10.5691 (4)0.8192 (4)0.17484 (12)0.0759 (7)
H10.6801560.8716490.2060320.091*
C20.5967 (5)0.8079 (4)0.10029 (13)0.0979 (9)
H20.7254990.8541120.0823480.117*
C30.4416 (5)0.7314 (4)0.05273 (13)0.0932 (8)
H30.4628790.7227110.0025610.112*
C40.2536 (5)0.6676 (4)0.08016 (13)0.0966 (9)
H40.1440140.61570.0482480.116*
C50.2219 (4)0.6782 (3)0.15497 (11)0.0776 (7)
H50.0913890.6332260.1721780.093*
C60.3793 (3)0.7539 (2)0.20421 (9)0.0472 (4)
C70.5393 (3)0.8071 (3)0.32686 (9)0.0497 (4)
H7A0.6263470.9046860.311470.06*
H7B0.6268340.7031060.3207240.06*
C80.4853 (3)0.8506 (3)0.40599 (10)0.0534 (5)
H8A0.6191960.8657460.4350070.064*
H8B0.4101390.9609430.4133350.064*
C90.1390 (3)0.6889 (3)0.38632 (10)0.0554 (5)
H9A0.0621820.7983260.3948530.067*
H9B0.045310.5949890.4015990.067*
C100.1858 (3)0.6476 (3)0.30616 (9)0.0502 (5)
H10A0.2416030.5296120.2968890.06*
H10B0.0502440.6477490.2786080.06*
C110.3129 (3)0.7088 (2)0.62385 (9)0.0445 (4)
C120.2060 (3)0.7367 (2)0.69737 (9)0.0413 (4)
C130.2989 (3)0.6749 (3)0.75734 (10)0.0535 (5)
H130.4288450.6156750.7520620.064*
C140.2008 (4)0.7003 (3)0.82503 (11)0.0656 (6)
H140.2656610.6573290.8645560.079*
C150.0081 (4)0.7885 (3)0.83492 (11)0.0611 (5)
C16−0.0837 (3)0.8490 (3)0.77515 (11)0.0583 (5)
H16−0.2140790.9076280.7805090.07*
C170.0129 (3)0.8250 (2)0.70719 (10)0.0484 (4)
H17−0.0521630.8685190.6678390.058*
C18−0.0996 (5)0.8177 (4)0.90877 (13)0.0968 (9)
H18A−0.1719210.9278530.9137140.145*
H18B0.0095880.8210990.9466130.145*
H18C−0.2048290.7225250.9128770.145*
N10.3441 (2)0.77371 (19)0.28025 (7)0.0434 (4)
N20.3444 (2)0.7069 (2)0.43010 (8)0.0487 (4)
O10.4844 (2)0.62506 (19)0.61816 (7)0.0632 (4)
O20.2244 (2)0.77468 (19)0.57233 (7)0.0601 (4)
OW10.7937 (3)0.7241 (4)0.52207 (11)0.1232 (9)
HW10.926 (4)0.748 (5)0.542 (2)0.177 (17)*
HW20.702 (4)0.704 (4)0.5539 (13)0.119 (11)*
HN10.415 (3)0.605 (2)0.4225 (11)0.061 (6)*
HN20.310 (3)0.731 (3)0.4786 (9)0.065 (6)*
U11U22U33U12U13U23
C10.0620 (13)0.114 (2)0.0494 (12)−0.0113 (13)0.0106 (10)0.0080 (12)
C20.0883 (18)0.148 (3)0.0556 (15)−0.0138 (18)0.0233 (13)0.0120 (15)
C30.123 (2)0.109 (2)0.0456 (13)−0.0055 (18)0.0201 (15)0.0043 (13)
C40.130 (2)0.106 (2)0.0480 (13)−0.0340 (18)−0.0161 (14)0.0036 (13)
C50.0895 (16)0.0936 (17)0.0466 (12)−0.0337 (13)−0.0042 (11)0.0105 (11)
C60.0561 (11)0.0456 (10)0.0397 (9)0.0045 (8)0.0038 (8)0.0042 (7)
C70.0473 (10)0.0550 (11)0.0456 (10)−0.0123 (8)0.0008 (8)0.0070 (8)
C80.0581 (11)0.0569 (12)0.0440 (10)−0.0065 (9)−0.0031 (8)0.0045 (8)
C90.0439 (10)0.0734 (13)0.0494 (11)−0.0025 (9)0.0087 (8)0.0105 (9)
C100.0383 (9)0.0668 (12)0.0446 (10)−0.0056 (8)0.0005 (7)0.0064 (8)
C110.0429 (10)0.0454 (10)0.0432 (10)−0.0062 (8)0.0042 (7)0.0012 (7)
C120.0413 (9)0.0376 (9)0.0439 (9)−0.0047 (7)0.0046 (7)0.0025 (7)
C130.0525 (11)0.0601 (12)0.0479 (11)0.0081 (9)0.0012 (8)0.0054 (9)
C140.0798 (15)0.0739 (14)0.0439 (11)0.0046 (11)−0.0013 (10)0.0111 (9)
C150.0742 (14)0.0597 (12)0.0479 (11)−0.0009 (10)0.0167 (10)0.0012 (9)
C160.0577 (12)0.0554 (12)0.0614 (12)0.0098 (9)0.0173 (9)0.0025 (9)
C170.0525 (10)0.0458 (10)0.0476 (10)0.0047 (8)0.0056 (8)0.0072 (8)
C180.125 (2)0.108 (2)0.0567 (14)0.0110 (17)0.0378 (15)0.0048 (13)
N10.0436 (8)0.0487 (8)0.0379 (8)−0.0025 (6)0.0016 (6)0.0068 (6)
N20.0519 (9)0.0577 (10)0.0371 (8)0.0057 (8)0.0054 (7)0.0068 (7)
O10.0546 (8)0.0720 (9)0.0633 (9)0.0149 (7)0.0170 (6)0.0047 (7)
O20.0557 (8)0.0833 (10)0.0426 (7)0.0032 (7)0.0096 (6)0.0120 (7)
OW10.0607 (12)0.250 (3)0.0691 (12)0.0102 (15)0.0088 (10)0.0577 (15)
C1—C21.379 (3)C10—H10A0.97
C1—C61.385 (3)C10—H10B0.97
C1—H10.93C11—O11.249 (2)
C2—C31.349 (4)C11—O21.260 (2)
C2—H20.93C11—C121.504 (2)
C3—C41.356 (4)C12—C131.385 (2)
C3—H30.93C12—C171.386 (2)
C4—C51.388 (3)C13—C141.384 (3)
C4—H40.93C13—H130.93
C5—C61.375 (3)C14—C151.383 (3)
C5—H50.93C14—H140.93
C6—N11.411 (2)C15—C161.374 (3)
C7—N11.461 (2)C15—C181.512 (3)
C7—C81.497 (2)C16—C171.384 (2)
C7—H7A0.97C16—H160.93
C7—H7B0.97C17—H170.93
C8—N21.481 (2)C18—H18A0.96
C8—H8A0.97C18—H18B0.96
C8—H8B0.97C18—H18C0.96
C9—N21.481 (2)N2—HN10.900 (15)
C9—C101.504 (2)N2—HN20.918 (15)
C9—H9A0.97OW1—HW10.886 (19)
C9—H9B0.97OW1—HW20.839 (18)
C10—N11.462 (2)
C2—C1—C6121.3 (2)C9—C10—H10B109
C2—C1—H1119.3H10A—C10—H10B107.8
C6—C1—H1119.3O1—C11—O2124.44 (16)
C3—C2—C1121.6 (2)O1—C11—C12118.17 (16)
C3—C2—H2119.2O2—C11—C12117.37 (15)
C1—C2—H2119.2C13—C12—C17118.11 (16)
C2—C3—C4118.1 (2)C13—C12—C11120.69 (15)
C2—C3—H3120.9C17—C12—C11121.19 (15)
C4—C3—H3120.9C14—C13—C12120.81 (17)
C3—C4—C5121.2 (2)C14—C13—H13119.6
C3—C4—H4119.4C12—C13—H13119.6
C5—C4—H4119.4C15—C14—C13121.14 (19)
C6—C5—C4121.4 (2)C15—C14—H14119.4
C6—C5—H5119.3C13—C14—H14119.4
C4—C5—H5119.3C16—C15—C14117.78 (17)
C5—C6—C1116.25 (18)C16—C15—C18120.7 (2)
C5—C6—N1121.84 (18)C14—C15—C18121.5 (2)
C1—C6—N1121.81 (17)C15—C16—C17121.68 (18)
N1—C7—C8112.51 (14)C15—C16—H16119.2
N1—C7—H7A109.1C17—C16—H16119.2
C8—C7—H7A109.1C16—C17—C12120.47 (17)
N1—C7—H7B109.1C16—C17—H17119.8
C8—C7—H7B109.1C12—C17—H17119.8
H7A—C7—H7B107.8C15—C18—H18A109.5
N2—C8—C7110.19 (15)C15—C18—H18B109.5
N2—C8—H8A109.6H18A—C18—H18B109.5
C7—C8—H8A109.6C15—C18—H18C109.5
N2—C8—H8B109.6H18A—C18—H18C109.5
C7—C8—H8B109.6H18B—C18—H18C109.5
H8A—C8—H8B108.1C6—N1—C7116.19 (14)
N2—C9—C10110.84 (14)C6—N1—C10116.09 (14)
N2—C9—H9A109.5C7—N1—C10113.11 (13)
C10—C9—H9A109.5C8—N2—C9108.70 (15)
N2—C9—H9B109.5C8—N2—HN1108.9 (13)
C10—C9—H9B109.5C9—N2—HN1109.5 (13)
H9A—C9—H9B108.1C8—N2—HN2111.2 (13)
N1—C10—C9112.96 (15)C9—N2—HN2108.7 (13)
N1—C10—H10A109HN1—N2—HN2109.8 (18)
C9—C10—H10A109HW1—OW1—HW2111 (3)
N1—C10—H10B109
C6—C1—C2—C3−0.7 (5)C13—C14—C15—C160.4 (3)
C1—C2—C3—C41.1 (5)C13—C14—C15—C18−179.7 (2)
C2—C3—C4—C5−0.8 (5)C14—C15—C16—C17−0.6 (3)
C3—C4—C5—C60.1 (4)C18—C15—C16—C17179.5 (2)
C4—C5—C6—C10.4 (4)C15—C16—C17—C120.7 (3)
C4—C5—C6—N1176.6 (2)C13—C12—C17—C16−0.5 (3)
C2—C1—C6—C5−0.1 (4)C11—C12—C17—C16179.76 (17)
C2—C1—C6—N1−176.3 (2)C5—C6—N1—C7162.90 (19)
N1—C7—C8—N256.4 (2)C1—C6—N1—C7−21.0 (3)
N2—C9—C10—N1−53.3 (2)C5—C6—N1—C1026.2 (3)
O1—C11—C12—C131.6 (2)C1—C6—N1—C10−157.72 (19)
O2—C11—C12—C13−177.16 (17)C8—C7—N1—C6172.21 (15)
O1—C11—C12—C17−178.61 (16)C8—C7—N1—C10−49.8 (2)
O2—C11—C12—C172.6 (2)C9—C10—N1—C6−173.76 (14)
C17—C12—C13—C140.3 (3)C9—C10—N1—C748.2 (2)
C11—C12—C13—C14−179.94 (18)C7—C8—N2—C9−60.59 (19)
C12—C13—C14—C15−0.3 (3)C10—C9—N2—C859.1 (2)
D—H···AD—HH···AD···AD—H···A
OW1—HW1···O2i0.89 (3)1.90 (3)2.782 (2)171 (4)
OW1—HW2···O10.84 (2)1.92 (3)2.751 (2)172 (3)
N2—HN1···O1ii0.90 (2)1.94 (2)2.819 (2)164 (2)
N2—HN2···O20.92 (2)1.80 (2)2.7207 (19)176 (2)
C8—H8A···OW10.972.333.116 (3)138
C10H15N2+·C2F3O2−·0.123H2OZ = 4
Mr = 278.47F(000) = 580.9
Triclinic, P1Dx = 1.371 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6544 (6) ÅCell parameters from 3827 reflections
b = 9.9029 (6) Åθ = 2.6–27.7°
c = 15.2090 (9) ŵ = 0.12 mm−1
α = 79.621 (6)°T = 293 K
β = 86.579 (6)°Prism, colourless
γ = 70.603 (6)°0.48 × 0.48 × 0.36 mm
V = 1349.10 (15) Å3
Oxford Diffraction Xcalibur diffractometer2777 reflections with I > 2σ(I)
ω scansRint = 0.014
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)θmax = 25.3°, θmin = 2.6°
Tmin = 0.724, Tmax = 1.000h = −11→11
9220 measured reflectionsk = −11→11
4940 independent reflectionsl = −18→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: mixed
wR(F2) = 0.235H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1128P)2 + 0.3819P] where P = (Fo2 + 2Fc2)/3
4927 reflections(Δ/σ)max < 0.001
375 parametersΔρmax = 0.42 e Å−3
4 restraintsΔρmin = −0.28 e Å−3
0 constraints
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
xyzUiso*/UeqOcc. (<1)
C10.2559 (3)0.7294 (3)0.51366 (18)0.0565 (7)
C20.1392 (4)0.7473 (3)0.5737 (2)0.0733 (9)
H20.0437650.7757040.5523060.088*
C30.1634 (5)0.7235 (4)0.6648 (3)0.0913 (12)
H30.0839760.7371610.7038370.11*
C40.3019 (6)0.6803 (4)0.6979 (2)0.0945 (12)
H40.3174360.6643410.7592460.113*
C50.4172 (5)0.6606 (4)0.6405 (3)0.0939 (11)
H50.5122090.6302050.662990.113*
C60.3958 (4)0.6850 (4)0.5497 (2)0.0746 (9)
H60.4766390.6715530.5117240.089*
C70.3582 (4)0.7522 (4)0.3646 (2)0.0748 (9)
H7A0.4396780.6653460.3853640.09*
H7B0.3865520.8356030.3698380.09*
C80.3289 (5)0.7565 (4)0.2686 (2)0.0924 (11)
H8A0.414070.7625860.2329660.111*
H8B0.3115970.6678920.2618530.111*
C90.0709 (5)0.8815 (5)0.2926 (3)0.1078 (14)
H9A0.0448360.7966480.2875420.129*
H9B−0.012110.9672250.2724410.129*
C100.1038 (4)0.8774 (5)0.3876 (2)0.0933 (12)
H10A0.1215560.9663250.3930670.112*
H10B0.0191880.8724670.4241280.112*
C110.7162 (3)0.7837 (3)0.34093 (18)0.0568 (7)
C120.6756 (3)0.9091 (3)0.3787 (2)0.0682 (8)
H120.6379950.9991790.3422890.082*
C130.6902 (4)0.9023 (4)0.4692 (2)0.0777 (9)
H130.6606530.9876870.4929380.093*
C140.7475 (4)0.7719 (5)0.5247 (2)0.0786 (10)
H140.7586720.7678910.5855290.094*
C150.7878 (4)0.6476 (4)0.4884 (2)0.0856 (10)
H150.8264680.5580960.5252590.103*
C160.7723 (4)0.6527 (4)0.3984 (2)0.0760 (9)
H160.7999690.5664710.3756250.091*
C170.8021 (5)0.6701 (4)0.2099 (2)0.0988 (13)
H17A0.8072680.5774570.2463370.119*
H17B0.8983260.6808750.210270.119*
C180.7624 (6)0.6706 (5)0.1152 (3)0.1280 (18)
H18A0.8379370.5948740.0904340.154*
H18B0.6703360.651260.1148430.154*
C190.6330 (5)0.9270 (5)0.0978 (2)0.0940 (11)
H19A0.5402150.9093150.0965670.113*
H19B0.6226681.0211690.0617050.113*
C200.6691 (4)0.9279 (4)0.1919 (2)0.0773 (9)
H20A0.7561790.956050.1918130.093*
H20B0.588820.9999960.2161840.093*
C210.2670 (4)0.2041 (4)0.1833 (2)0.0776 (9)
C220.2420 (8)0.3636 (6)0.1772 (3)0.1240 (19)0.736 (3)
C22'0.2420 (8)0.3636 (6)0.1772 (3)0.1240 (19)0.264 (3)
C230.1345 (7)0.8145 (4)0.0390 (2)0.0940 (13)
C240.1356 (7)0.7597 (5)−0.0474 (3)0.1064 (14)0.736 (3)
C24'0.1356 (7)0.7597 (5)−0.0474 (3)0.1064 (14)0.264 (3)
N10.2321 (3)0.7528 (2)0.42089 (15)0.0596 (6)
N20.1985 (4)0.8842 (3)0.23622 (18)0.0888 (9)
N30.6944 (3)0.7878 (3)0.24907 (15)0.0687 (7)
N40.7485 (4)0.8143 (4)0.05995 (19)0.1087 (12)
O10.2367 (4)0.1448 (3)0.25394 (17)0.1168 (10)
O20.3178 (4)0.1492 (4)0.11854 (18)0.1323 (12)
O30.2462 (4)0.8383 (4)0.05509 (19)0.1252 (11)
O40.0222 (4)0.8316 (3)0.08423 (17)0.1113 (10)
F10.3669 (7)0.3949 (7)0.1721 (5)0.202 (3)0.736 (3)
F20.1775 (9)0.4242 (5)0.2477 (4)0.184 (3)0.736 (3)
F30.1706 (8)0.4421 (5)0.1039 (4)0.179 (3)0.736 (3)
F1'0.302 (2)0.407 (2)0.0998 (15)0.202 (3)0.264 (3)
F2'0.282 (3)0.3950 (17)0.2311 (15)0.184 (3)0.264 (3)
F3'0.102 (2)0.4303 (16)0.1642 (11)0.179 (3)0.264 (3)
F40.2609 (7)0.6549 (8)−0.0615 (4)0.175 (2)0.736 (3)
F50.1187 (10)0.8524 (4)−0.1159 (2)0.181 (3)0.736 (3)
F60.0480 (7)0.6817 (8)−0.0460 (4)0.153 (2)0.736 (3)
F4'0.238 (2)0.789 (2)−0.1015 (13)0.175 (2)0.264 (3)
F5'0.157 (4)0.6370 (19)−0.0412 (9)0.181 (3)0.264 (3)
F6'−0.0072 (19)0.8256 (19)−0.0913 (10)0.153 (2)0.264 (3)
OW10.5122 (12)0.6320 (14)0.0361 (10)0.150 (8)0.245 (10)
H210.2073180.9693760.2382270.18*
H220.1875960.8867170.1796960.18*
H410.8265980.8389530.0538350.18*
H420.7220960.8107840.0058060.18*
HW1A0.5720850.618747−0.0073060.225*0.245 (10)
HW1B0.4416750.7076380.0158740.225*0.245 (10)
U11U22U33U12U13U23
C10.065 (2)0.0490 (15)0.0531 (16)−0.0184 (13)0.0022 (14)−0.0040 (12)
C20.075 (2)0.069 (2)0.068 (2)−0.0195 (16)0.0111 (17)−0.0051 (15)
C30.116 (3)0.074 (2)0.075 (2)−0.025 (2)0.033 (2)−0.0120 (18)
C40.141 (4)0.079 (2)0.056 (2)−0.028 (2)−0.001 (2)−0.0089 (17)
C50.107 (3)0.098 (3)0.072 (2)−0.025 (2)−0.026 (2)−0.0087 (19)
C60.064 (2)0.089 (2)0.066 (2)−0.0204 (17)−0.0069 (16)−0.0074 (16)
C70.073 (2)0.086 (2)0.0618 (18)−0.0228 (17)0.0105 (16)−0.0132 (16)
C80.122 (3)0.098 (3)0.062 (2)−0.039 (2)0.010 (2)−0.0215 (19)
C90.099 (3)0.139 (4)0.079 (3)−0.044 (3)−0.030 (2)0.017 (2)
C100.065 (2)0.128 (3)0.063 (2)−0.010 (2)−0.0084 (17)0.0067 (19)
C110.0597 (18)0.0649 (18)0.0512 (15)−0.0254 (14)0.0087 (13)−0.0168 (13)
C120.086 (2)0.0636 (18)0.0605 (17)−0.0280 (16)0.0031 (15)−0.0183 (14)
C130.089 (2)0.093 (2)0.066 (2)−0.0390 (19)0.0122 (18)−0.0374 (19)
C140.076 (2)0.119 (3)0.0513 (17)−0.044 (2)0.0031 (16)−0.019 (2)
C150.092 (3)0.093 (3)0.063 (2)−0.024 (2)−0.0075 (18)−0.0006 (18)
C160.091 (2)0.065 (2)0.066 (2)−0.0172 (16)0.0037 (17)−0.0140 (15)
C170.167 (4)0.071 (2)0.064 (2)−0.042 (2)0.028 (2)−0.0283 (17)
C180.221 (6)0.115 (4)0.074 (3)−0.078 (4)0.039 (3)−0.050 (2)
C190.118 (3)0.118 (3)0.0538 (19)−0.051 (2)0.0026 (19)−0.0131 (19)
C200.094 (3)0.076 (2)0.0602 (18)−0.0257 (18)−0.0026 (17)−0.0121 (16)
C210.102 (3)0.086 (2)0.0458 (17)−0.0309 (19)−0.0063 (17)−0.0135 (16)
C220.194 (6)0.122 (4)0.068 (3)−0.074 (4)−0.044 (3)0.011 (3)
C22'0.194 (6)0.122 (4)0.068 (3)−0.074 (4)−0.044 (3)0.011 (3)
C230.159 (4)0.066 (2)0.052 (2)−0.032 (2)0.011 (3)−0.0113 (16)
C240.172 (5)0.084 (3)0.070 (2)−0.047 (3)0.028 (3)−0.028 (2)
C24'0.172 (5)0.084 (3)0.070 (2)−0.047 (3)0.028 (3)−0.028 (2)
N10.0591 (15)0.0674 (15)0.0519 (13)−0.0234 (12)−0.0030 (11)−0.0028 (11)
N20.136 (3)0.082 (2)0.0530 (15)−0.0447 (19)−0.0139 (17)−0.0015 (13)
N30.094 (2)0.0709 (16)0.0501 (13)−0.0357 (14)0.0087 (12)−0.0184 (12)
N40.162 (3)0.127 (3)0.0538 (16)−0.066 (2)0.0207 (19)−0.0303 (18)
O10.205 (3)0.0908 (18)0.0635 (16)−0.0618 (19)0.0128 (17)−0.0133 (13)
O20.163 (3)0.164 (3)0.0675 (16)−0.038 (2)0.0098 (17)−0.0474 (18)
O30.161 (3)0.157 (3)0.0719 (18)−0.062 (3)0.0133 (19)−0.0395 (18)
O40.154 (3)0.121 (2)0.0633 (15)−0.0477 (19)0.0290 (17)−0.0313 (14)
F10.249 (6)0.248 (6)0.198 (6)−0.196 (5)−0.015 (4)−0.040 (4)
F20.289 (8)0.078 (3)0.159 (4)−0.016 (4)0.037 (5)−0.053 (2)
F30.278 (7)0.117 (3)0.142 (4)−0.095 (3)−0.104 (5)0.068 (3)
F1'0.249 (6)0.248 (6)0.198 (6)−0.196 (5)−0.015 (4)−0.040 (4)
F2'0.289 (8)0.078 (3)0.159 (4)−0.016 (4)0.037 (5)−0.053 (2)
F3'0.278 (7)0.117 (3)0.142 (4)−0.095 (3)−0.104 (5)0.068 (3)
F40.227 (5)0.149 (4)0.137 (4)−0.024 (4)0.046 (3)−0.082 (4)
F50.411 (11)0.084 (2)0.0504 (17)−0.087 (4)−0.014 (3)0.0007 (16)
F60.226 (5)0.152 (4)0.118 (3)−0.092 (4)0.009 (3)−0.061 (3)
F4'0.227 (5)0.149 (4)0.137 (4)−0.024 (4)0.046 (3)−0.082 (4)
F5'0.411 (11)0.084 (2)0.0504 (17)−0.087 (4)−0.014 (3)0.0007 (16)
F6'0.226 (5)0.152 (4)0.118 (3)−0.092 (4)0.009 (3)−0.061 (3)
OW10.082 (10)0.146 (13)0.219 (18)−0.019 (8)−0.031 (9)−0.048 (11)
C1—C61.388 (4)C17—C181.512 (5)
C1—C21.392 (4)C17—H17A0.97
C1—N11.408 (3)C17—H17B0.97
C2—C31.384 (5)C18—N41.485 (6)
C2—H20.93C18—H18A0.97
C3—C41.359 (6)C18—H18B0.97
C3—H30.93C19—N41.465 (5)
C4—C51.357 (5)C19—C201.495 (4)
C4—H40.93C19—H19A0.97
C5—C61.375 (5)C19—H19B0.97
C5—H50.93C20—N31.451 (4)
C6—H60.93C20—H20A0.97
C7—N11.445 (4)C20—H20B0.97
C7—C81.494 (5)C21—O11.197 (4)
C7—H7A0.97C21—O21.211 (4)
C7—H7B0.97C21—C22'1.502 (7)
C8—N21.489 (5)C21—C221.502 (7)
C8—H8A0.97C22—F31.321 (6)
C8—H8B0.97C22—F11.337 (7)
C9—N21.464 (5)C22—F21.343 (7)
C9—C101.488 (5)C22'—F2'1.06 (2)
C9—H9A0.97C22'—F3'1.306 (19)
C9—H9B0.97C22'—F1'1.346 (19)
C10—N11.466 (4)C23—O31.224 (5)
C10—H10A0.97C23—O41.228 (5)
C10—H10B0.97C23—C24'1.506 (6)
C11—C161.386 (4)C23—C241.506 (6)
C11—C121.390 (4)C24—F51.238 (5)
C11—N31.417 (3)C24—F61.319 (7)
C12—C131.379 (4)C24—F41.342 (7)
C12—H120.93C24'—F5'1.151 (17)
C13—C141.369 (5)C24'—F4'1.32 (2)
C13—H130.93C24'—F6'1.459 (17)
C14—C151.368 (5)N2—H210.8818
C14—H140.93N2—H220.8672
C15—C161.377 (5)N4—H410.8621
C15—H150.93N4—H420.8861
C16—H160.93OW1—HW1A0.8501
C17—N31.471 (4)OW1—HW1B0.8501
C6—C1—C2116.9 (3)N4—C18—H18B109.8
C6—C1—N1122.0 (3)C17—C18—H18B109.8
C2—C1—N1121.1 (3)H18A—C18—H18B108.2
C3—C2—C1120.8 (3)N4—C19—C20110.7 (3)
C3—C2—H2119.6N4—C19—H19A109.5
C1—C2—H2119.6C20—C19—H19A109.5
C4—C3—C2120.8 (3)N4—C19—H19B109.5
C4—C3—H3119.6C20—C19—H19B109.5
C2—C3—H3119.6H19A—C19—H19B108.1
C5—C4—C3119.2 (4)N3—C20—C19112.8 (3)
C5—C4—H4120.4N3—C20—H20A109
C3—C4—H4120.4C19—C20—H20A109
C4—C5—C6121.0 (4)N3—C20—H20B109
C4—C5—H5119.5C19—C20—H20B109
C6—C5—H5119.5H20A—C20—H20B107.8
C5—C6—C1121.2 (3)O1—C21—O2127.2 (4)
C5—C6—H6119.4O1—C21—C22'115.1 (4)
C1—C6—H6119.4O2—C21—C22'117.7 (4)
N1—C7—C8112.5 (3)O1—C21—C22115.1 (4)
N1—C7—H7A109.1O2—C21—C22117.7 (4)
C8—C7—H7A109.1F3—C22—F1103.5 (5)
N1—C7—H7B109.1F3—C22—F2108.8 (6)
C8—C7—H7B109.1F1—C22—F2100.9 (6)
H7A—C7—H7B107.8F3—C22—C21112.7 (4)
N2—C8—C7110.4 (3)F1—C22—C21112.9 (6)
N2—C8—H8A109.6F2—C22—C21116.7 (4)
C7—C8—H8A109.6F2'—C22'—F3'112.1 (15)
N2—C8—H8B109.6F2'—C22'—F1'110.0 (16)
C7—C8—H8B109.6F3'—C22'—F1'103.4 (13)
H8A—C8—H8B108.1F2'—C22'—C21116.5 (11)
N2—C9—C10110.4 (3)F3'—C22'—C21106.9 (7)
N2—C9—H9A109.6F1'—C22'—C21107.0 (10)
C10—C9—H9A109.6O3—C23—O4127.7 (4)
N2—C9—H9B109.6O3—C23—C24'115.5 (5)
C10—C9—H9B109.6O4—C23—C24'116.8 (5)
H9A—C9—H9B108.1O3—C23—C24115.5 (5)
N1—C10—C9112.1 (3)O4—C23—C24116.8 (5)
N1—C10—H10A109.2F5—C24—F6111.9 (6)
C9—C10—H10A109.2F5—C24—F4104.5 (6)
N1—C10—H10B109.2F6—C24—F496.7 (5)
C9—C10—H10B109.2F5—C24—C23115.4 (4)
H10A—C10—H10B107.9F6—C24—C23113.1 (4)
C16—C11—C12116.8 (3)F4—C24—C23113.6 (5)
C16—C11—N3121.0 (2)F5'—C24'—F4'106.2 (16)
C12—C11—N3122.0 (3)F5'—C24'—F6'103.6 (18)
C13—C12—C11121.1 (3)F4'—C24'—F6'109.6 (11)
C13—C12—H12119.4F5'—C24'—C23116.0 (8)
C11—C12—H12119.4F4'—C24'—C23110.3 (9)
C14—C13—C12121.1 (3)F6'—C24'—C23110.7 (6)
C14—C13—H13119.4C1—N1—C7116.1 (2)
C12—C13—H13119.4C1—N1—C10115.0 (2)
C15—C14—C13118.3 (3)C7—N1—C10110.5 (2)
C15—C14—H14120.8C9—N2—C8110.4 (3)
C13—C14—H14120.8C9—N2—H21104.1
C14—C15—C16121.2 (3)C8—N2—H21115
C14—C15—H15119.4C9—N2—H22115.8
C16—C15—H15119.4C8—N2—H22108.2
C15—C16—C11121.4 (3)H21—N2—H22103.4
C15—C16—H16119.3C11—N3—C20115.9 (2)
C11—C16—H16119.3C11—N3—C17114.7 (3)
N3—C17—C18111.9 (4)C20—N3—C17111.7 (2)
N3—C17—H17A109.2C19—N4—C18109.0 (3)
C18—C17—H17A109.2C19—N4—H41108.2
N3—C17—H17B109.2C18—N4—H41116.5
C18—C17—H17B109.2C19—N4—H42109.5
H17A—C17—H17B107.9C18—N4—H42106.4
N4—C18—C17109.5 (3)H41—N4—H42107.1
N4—C18—H18A109.8HW1A—OW1—HW1B104.5
C17—C18—H18A109.8
C6—C1—C2—C30.8 (4)O3—C23—C24—F5−75.6 (8)
N1—C1—C2—C3179.7 (3)O4—C23—C24—F5103.6 (7)
C1—C2—C3—C4−0.8 (5)O3—C23—C24—F6153.8 (6)
C2—C3—C4—C50.1 (6)O4—C23—C24—F6−26.9 (7)
C3—C4—C5—C60.6 (6)O3—C23—C24—F444.9 (7)
C4—C5—C6—C1−0.5 (6)O4—C23—C24—F4−135.8 (6)
C2—C1—C6—C5−0.2 (5)O3—C23—C24'—F5'102 (2)
N1—C1—C6—C5−179.0 (3)O4—C23—C24'—F5'−79 (2)
N1—C7—C8—N255.4 (4)O3—C23—C24'—F4'−18.9 (12)
N2—C9—C10—N1−57.1 (5)O4—C23—C24'—F4'160.3 (11)
C16—C11—C12—C13−0.3 (5)O3—C23—C24'—F6'−140.4 (8)
N3—C11—C12—C13176.4 (3)O4—C23—C24'—F6'38.8 (9)
C11—C12—C13—C141.1 (5)C6—C1—N1—C7−10.1 (4)
C12—C13—C14—C15−1.1 (5)C2—C1—N1—C7171.1 (3)
C13—C14—C15—C160.3 (5)C6—C1—N1—C10−141.4 (3)
C14—C15—C16—C110.5 (6)C2—C1—N1—C1039.8 (4)
C12—C11—C16—C15−0.5 (5)C8—C7—N1—C1171.8 (3)
N3—C11—C16—C15−177.2 (3)C8—C7—N1—C10−54.8 (4)
N3—C17—C18—N456.6 (5)C9—C10—N1—C1−170.6 (3)
N4—C19—C20—N3−55.9 (4)C9—C10—N1—C755.5 (4)
O1—C21—C22—F3−132.4 (6)C10—C9—N2—C856.8 (4)
O2—C21—C22—F349.2 (8)C7—C8—N2—C9−55.8 (4)
O1—C21—C22—F1110.7 (6)C16—C11—N3—C20−165.9 (3)
O2—C21—C22—F1−67.7 (6)C12—C11—N3—C2017.6 (4)
O1—C21—C22—F2−5.5 (8)C16—C11—N3—C17−33.3 (4)
O2—C21—C22—F2176.1 (6)C12—C11—N3—C17150.2 (3)
O1—C21—C22'—F2'47.1 (18)C19—C20—N3—C11−174.6 (3)
O2—C21—C22'—F2'−131.3 (17)C19—C20—N3—C1751.5 (4)
O1—C21—C22'—F3'−79.2 (9)C18—C17—N3—C11173.3 (3)
O2—C21—C22'—F3'102.4 (10)C18—C17—N3—C20−52.1 (4)
O1—C21—C22'—F1'170.6 (10)C20—C19—N4—C1859.6 (4)
O2—C21—C22'—F1'−7.8 (12)C17—C18—N4—C19−60.0 (5)
D—H···AD—HH···AD···AD—H···A
N2—H21···O1i0.881.912.790 (4)174
N2—H22···O30.872.042.860 (4)157
N2—H22···O40.872.473.164 (5)137
N4—H41···O4ii0.861.952.759 (6)156
N4—H42···O2iii0.891.902.758 (4)164
C18—H18A···F5′iii0.972.533.273 (18)134
C18—H18B···Ow10.972.082.929 (15)145
C19—H19B···O3iv0.972.593.420 (5)144
C20—H20A···F5iv0.972.643.468 (8)144
C16—H16···Cg2v0.932.993.745 (4)140
  22 in total

1.  Pharmacokinetic evaluation of LASSBio-579: an N-phenylpiperazine antipsychotic prototype.

Authors:  Daniela J Conrado; Hugo Verli; Gilda Neves; Carlos Alberto Manssour Fraga; Eliezer J Barreiro; Stela Maris Kuze Rates; Teresa Dalla Costa
Journal:  J Pharm Pharmacol       Date:  2008-06       Impact factor: 3.765

2.  The cardiovascular and autonomic properties of N-phenylpiperazine (NPP) in several animal models.

Authors:  M R Cohen; E Hinsch; Z Palkoski; R Vergona; S Urbano; J Sztokalo
Journal:  J Pharmacol Exp Ther       Date:  1982-10       Impact factor: 4.030

3.  Substituted piperazines as novel dipeptidyl peptidase IV inhibitors.

Authors:  Linda L Brockunier; Jiafang He; Lawrence F Colwell; Bahanu Habulihaz; Huaibing He; Barbara Leiting; Kathryn A Lyons; Frank Marsilio; Reshma A Patel; Yohannes Teffera; Joseph K Wu; Nancy A Thornberry; Ann E Weber; Emma R Parmee
Journal:  Bioorg Med Chem Lett       Date:  2004-09-20       Impact factor: 2.823

4.  1-Phenyl-piperazine-1,4-diium bis-(hydrogen sulfate).

Authors:  Houda Marouani; Mohamed Rzaigui; Salem S Al-Deyab
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-25

5.  Crystal structures of 4-phenyl-piperazin-1-ium 6-chloro-5-ethyl-2,4-dioxopyrimidin-1-ide and 4-phenyl-piperazin-1-ium 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide.

Authors:  Monirah A Al-Alshaikh; Ali A El-Emam; Omar A Al-Deeb; Mohammed S M Abdelbaky; Santiago Garcia-Granda
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-07-22

6.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

7.  Six 1-aroyl-4-(4-meth-oxy-phen-yl)piperazines: similar mol-ecular structures but different patterns of supra-molecular assembly.

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Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-07-26

8.  checkCIF validation ALERTS: what they mean and how to respond.

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Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2020-01-01

9.  The Cambridge Structural Database.

Authors:  Colin R Groom; Ian J Bruno; Matthew P Lightfoot; Suzanna C Ward
Journal:  Acta Crystallogr B Struct Sci Cryst Eng Mater       Date:  2016-04-01

10.  Crystal structures of the recreational drug N-(4-meth-oxy-phen-yl)piperazine (MeOPP) and three of its salts.

Authors:  Haruvegowda Kiran Kumar; Hemmige S Yathirajan; Chayanna Harish Chinthal; Sabine Foro; Christopher Glidewell
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2020-03-05
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1.  The structures of eleven (4-phen-yl)piperazinium salts containing organic anions.

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