Literature DB >> 21522648

Imidazole-imidazolium picrate monohydrate.

Rodolfo Moreno-Fuquen, Regina De Almeida Santos, Lina Aguirre.   

Abstract

The asymmetric unit of the title compound, C(3)H(5)N(2) (+)·C(6)H(2)N(3)O(7) (-)·C(3)H(4)N(2)·H(2)O or H(C(3)H(4)N(2))(2) (+)·C(6)H(2)N(3)O(7) (-)·H(2)O, contains a diimidazolium cationic unit, one picrate anion and one mol-ecule of water. In the crystal, the components are connected by N-H⋯O, N-H⋯N and O-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (001). In addition, weak inter-molecular C-H⋯O hydrogen bonds lead to the formation of a three-dimensional network featuring R(5) (5)(19) rings.

Entities:  

Year:  2010        PMID： 21522648      PMCID： PMC3050159          DOI： 10.1107/S160053681005169X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to imidazolium salts see: Moreno-Fuquen et al. (2009a ▶,b ▶ ▶). For imidazole as an anti­fungal agent, see: Miranda et al. (1998 ▶); Rodriguez & Acosta (1997 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen-bond geometries, see: Emsley (1984 ▶); Etter (1990 ▶); Nardelli (1995 ▶).

Experimental

Crystal data

C3H5N2 +·C6H2N3O7 −·C3H4N2·H2O M = 383.29 Orthorhombic, a = 3.8180 (1) Å b = 20.8160 (8) Å c = 21.4420 (8) Å V = 1704.11 (10) Å3 Z = 4 Mo Kα radiation μ = 0.13 mm−1 T = 291 K 0.53 × 0.21 × 0.14 mm

Data collection

Bruker–Nonius KappaCCD diffractometer 12017 measured reflections 2207 independent reflections 1723 reflections with I > 2σ(I) R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.109 S = 1.06 2207 reflections 248 parameters H-atom parameters constrained Δρmax = 0.14 e Å−3 Δρmin = −0.15 e Å−3 Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005169X/lh5175sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681005169X/lh5175Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C3H5N2+·C6H2N3O7−·C3H4N2·H2ODx = 1.494 Mg m−3
Mr = 383.29Melting point: 494(1) K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6888 reflections
a = 3.8180 (1) Åθ = 2.9–27.1°
b = 20.8160 (8) ŵ = 0.13 mm−1
c = 21.4420 (8) ÅT = 291 K
V = 1704.11 (10) Å3Prism, yellow
Z = 40.53 × 0.21 × 0.14 mm
F(000) = 792
Bruker–Nonius KappaCCD diffractometer1723 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
horizonally mounted graphite crystalθmax = 27.1°, θmin = 3.0°
Detector resolution: 9 pixels mm-1h = −4→3
CCD scansk = −20→26
12017 measured reflectionsl = −27→26
2207 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0567P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3
2207 reflections(Δ/σ)max < 0.001
248 parametersΔρmax = 0.14 e Å−3
0 restraintsΔρmin = −0.15 e Å−3
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
O10.2191 (5)1.03522 (7)0.55396 (7)0.0571 (4)
O2−0.1566 (6)1.14493 (9)0.57670 (8)0.0731 (5)
O30.1895 (7)1.21912 (8)0.54543 (9)0.0788 (6)
O40.2390 (9)0.92426 (8)0.48892 (9)0.0914 (8)
O50.7228 (7)0.95183 (9)0.60361 (10)0.0802 (6)
O60.5569 (8)0.92982 (10)0.40721 (10)0.0965 (8)
O70.2812 (11)1.20386 (11)0.31429 (10)0.1096 (10)
O80.4859 (10)1.11533 (12)0.27852 (9)0.1128 (11)
N10.0590 (5)1.16612 (9)0.54037 (9)0.0515 (5)
N20.3639 (9)1.14743 (12)0.32037 (10)0.0774 (7)
N30.3776 (7)0.95481 (9)0.44756 (9)0.0622 (6)
N40.5815 (7)0.82430 (10)0.61111 (11)0.0659 (6)
N50.5551 (7)0.73058 (10)0.65339 (10)0.0660 (6)
H50.57420.69990.68000.079*
N60.6123 (7)0.63572 (11)0.73624 (9)0.0693 (6)
N70.7046 (8)0.58105 (11)0.82023 (9)0.0694 (7)
C10.2292 (6)1.05863 (10)0.50031 (9)0.0464 (5)
C20.1650 (6)1.12594 (10)0.48771 (9)0.0460 (5)
C30.2078 (7)1.15485 (10)0.43161 (10)0.0523 (6)
H310.16861.19870.42700.063*
C40.3112 (8)1.11772 (11)0.38114 (10)0.0540 (6)
C50.3698 (7)1.05261 (11)0.38734 (10)0.0530 (6)
H510.44051.02840.35320.064*
C60.3229 (7)1.02395 (10)0.44446 (10)0.0496 (5)
C70.4412 (8)0.78433 (12)0.56804 (12)0.0636 (7)
H710.37110.79520.52790.076*
C80.4228 (8)0.72631 (12)0.59449 (12)0.0648 (7)
H810.33480.68930.57590.078*
C90.6470 (9)0.79029 (14)0.66155 (12)0.0693 (7)
H910.74530.80660.69790.083*
C100.5174 (9)0.57373 (15)0.72587 (12)0.0726 (8)
H1010.42860.55770.68860.087*
C110.5717 (10)0.53967 (15)0.77749 (12)0.0766 (9)
H1110.52740.49610.78310.092*
C120.7269 (10)0.63802 (14)0.79433 (12)0.0729 (8)
H1210.81110.67470.81400.088*
H4010.64130.86800.60860.095 (10)*
H7010.75230.57180.85930.084 (9)*
H5010.56050.97920.58770.41 (7)*
H5020.92120.97400.58330.17 (2)*
U11U22U33U12U13U23
O10.0768 (12)0.0511 (8)0.0435 (7)−0.0053 (9)0.0018 (8)0.0016 (6)
O20.0723 (12)0.0860 (13)0.0609 (10)0.0056 (12)0.0146 (11)−0.0090 (10)
O30.0998 (15)0.0529 (9)0.0836 (12)0.0004 (11)−0.0011 (13)−0.0191 (9)
O40.152 (2)0.0493 (9)0.0731 (12)−0.0071 (13)0.0180 (16)0.0000 (9)
O50.0931 (16)0.0565 (10)0.0909 (13)−0.0093 (11)0.0083 (14)0.0037 (9)
O60.142 (2)0.0693 (11)0.0781 (12)0.0391 (14)0.0226 (16)−0.0082 (10)
O70.183 (3)0.0739 (13)0.0718 (12)0.0005 (19)0.0005 (19)0.0242 (11)
O80.180 (3)0.1017 (16)0.0570 (10)−0.005 (2)0.0428 (17)0.0030 (12)
N10.0532 (11)0.0501 (10)0.0514 (10)0.0066 (9)−0.0063 (10)−0.0048 (9)
N20.108 (2)0.0727 (14)0.0519 (12)−0.0131 (16)0.0059 (14)0.0083 (11)
N30.0874 (16)0.0495 (10)0.0498 (10)0.0086 (12)−0.0034 (12)−0.0073 (9)
N40.0724 (15)0.0513 (11)0.0742 (13)−0.0013 (11)0.0062 (12)−0.0015 (10)
N50.0846 (16)0.0611 (12)0.0525 (11)−0.0011 (12)−0.0043 (12)0.0073 (10)
N60.0808 (16)0.0752 (14)0.0520 (11)0.0021 (14)−0.0064 (12)0.0104 (10)
N70.0958 (18)0.0699 (13)0.0425 (10)0.0095 (14)−0.0023 (12)0.0080 (10)
C10.0505 (13)0.0450 (10)0.0437 (11)−0.0041 (10)−0.0014 (10)−0.0019 (9)
C20.0462 (12)0.0459 (10)0.0460 (10)0.0010 (10)−0.0026 (10)−0.0058 (9)
C30.0582 (14)0.0442 (11)0.0545 (12)0.0004 (11)−0.0052 (12)0.0008 (10)
C40.0626 (15)0.0556 (12)0.0439 (11)−0.0069 (12)−0.0005 (11)0.0059 (10)
C50.0580 (14)0.0578 (12)0.0433 (11)0.0015 (12)0.0029 (11)−0.0063 (10)
C60.0570 (14)0.0437 (11)0.0481 (11)0.0008 (11)−0.0022 (11)−0.0034 (9)
C70.0769 (19)0.0611 (14)0.0529 (13)0.0032 (14)−0.0062 (13)0.0025 (11)
C80.0818 (19)0.0564 (13)0.0562 (13)−0.0061 (14)−0.0071 (14)−0.0028 (11)
C90.0819 (19)0.0720 (16)0.0541 (14)−0.0056 (16)−0.0044 (15)−0.0119 (13)
C100.084 (2)0.0856 (18)0.0482 (13)−0.0080 (18)−0.0031 (15)−0.0003 (13)
C110.104 (3)0.0689 (15)0.0567 (14)−0.0112 (18)0.0035 (16)0.0030 (13)
C120.098 (2)0.0665 (15)0.0542 (13)0.0016 (17)−0.0076 (16)0.0045 (12)
O1—C11.250 (2)N7—C121.312 (3)
O2—N11.216 (3)N7—C111.356 (4)
O3—N11.216 (3)N7—H7010.880
O4—N31.213 (3)C1—C61.443 (3)
O5—H5010.908C1—C21.448 (3)
O5—H5020.988C2—C31.355 (3)
O6—N31.220 (3)C3—C41.387 (3)
O7—N21.223 (3)C3—H310.9300
O8—N21.212 (3)C4—C51.380 (3)
N1—C21.462 (3)C5—C61.374 (3)
N2—C41.456 (3)C5—H510.9300
N3—C61.456 (3)C7—C81.336 (4)
N4—C91.317 (3)C7—H710.9300
N4—C71.354 (3)C8—H810.9300
N4—H4010.940C9—H910.9300
N5—C91.303 (3)C10—C111.331 (4)
N5—C81.363 (3)C10—H1010.9300
N5—H50.8600C11—H1110.9300
N6—C121.321 (3)C12—H1210.9300
N6—C101.359 (4)
H501—O5—H50293.71C4—C3—H31120.7
O3—N1—O2123.3 (2)C5—C4—C3121.2 (2)
O3—N1—C2118.3 (2)C5—C4—N2118.7 (2)
O2—N1—C2118.34 (19)C3—C4—N2120.0 (2)
O8—N2—O7123.4 (2)C6—C5—C4119.4 (2)
O8—N2—C4118.8 (2)C6—C5—H51120.3
O7—N2—C4117.9 (3)C4—C5—H51120.3
O4—N3—O6122.7 (2)C5—C6—C1123.69 (19)
O4—N3—C6119.3 (2)C5—C6—N3116.8 (2)
O6—N3—C6118.0 (2)C1—C6—N3119.48 (19)
C9—N4—C7107.8 (2)C8—C7—N4106.7 (2)
C9—N4—H401121.4C8—C7—H71126.7
C7—N4—H401130.8N4—C7—H71126.7
C9—N5—C8106.6 (2)C7—C8—N5108.4 (2)
C9—N5—H5126.7C7—C8—H81125.8
C8—N5—H5126.7N5—C8—H81125.8
C12—N6—C10106.1 (2)N5—C9—N4110.6 (2)
C12—N7—C11108.2 (2)N5—C9—H91124.7
C12—N7—H701126.0N4—C9—H91124.7
C11—N7—H701125.6C11—C10—N6109.2 (2)
O1—C1—C6125.19 (19)C11—C10—H101125.4
O1—C1—C2122.94 (19)N6—C10—H101125.4
C6—C1—C2111.79 (17)C10—C11—N7106.4 (3)
C3—C2—C1125.10 (19)C10—C11—H111126.8
C3—C2—N1117.70 (18)N7—C11—H111126.8
C1—C2—N1117.15 (17)N7—C12—N6110.2 (3)
C2—C3—C4118.6 (2)N7—C12—H121124.9
C2—C3—H31120.7N6—C12—H121124.9
O1—C1—C2—C3172.9 (3)C4—C5—C6—N3178.0 (3)
C6—C1—C2—C3−4.0 (4)O1—C1—C6—C5−172.4 (3)
O1—C1—C2—N1−4.6 (4)C2—C1—C6—C54.4 (4)
C6—C1—C2—N1178.5 (2)O1—C1—C6—N36.7 (4)
O3—N1—C2—C3−40.4 (3)C2—C1—C6—N3−176.5 (2)
O2—N1—C2—C3139.3 (2)O4—N3—C6—C5−156.8 (3)
O3—N1—C2—C1137.3 (2)O6—N3—C6—C521.7 (4)
O2—N1—C2—C1−43.0 (3)O4—N3—C6—C124.0 (4)
C1—C2—C3—C42.0 (4)O6—N3—C6—C1−157.5 (3)
N1—C2—C3—C4179.5 (2)C9—N4—C7—C80.6 (3)
C2—C3—C4—C50.1 (4)N4—C7—C8—N5−0.6 (3)
C2—C3—C4—N2−179.2 (3)C9—N5—C8—C70.5 (4)
O8—N2—C4—C5−6.2 (5)C8—N5—C9—N4−0.1 (4)
O7—N2—C4—C5173.6 (3)C7—N4—C9—N5−0.3 (4)
O8—N2—C4—C3173.1 (3)C12—N6—C10—C110.6 (4)
O7—N2—C4—C3−7.1 (5)N6—C10—C11—N7−0.5 (4)
C3—C4—C5—C60.4 (4)C12—N7—C11—C100.1 (4)
N2—C4—C5—C6179.7 (3)C11—N7—C12—N60.2 (4)
C4—C5—C6—C1−2.9 (4)C10—N6—C12—N7−0.5 (4)
D—H···AD—HH···AD···AD—H···A
N5—H5···N60.861.812.666 (3)180
N4—H401···O50.941.782.714 (3)176
O5—H501···O10.911.902.801 (3)179
O5—H502···O1i0.991.822.782 (3)163
N7—H701···O1ii0.882.012.876 (2)167
C10—H101···O6iii0.932.513.352 (4)151
C9—H91···O8iv0.932.583.481 (3)162
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N5—H5⋯N60.861.812.666 (3)180
N4—H401⋯O50.941.782.714 (3)176
O5—H501⋯O10.911.902.801 (3)179
O5—H502⋯O1i0.991.822.782 (3)163
N7—H701⋯O1ii0.882.012.876 (2)167
C10—H101⋯O6iii0.932.513.352 (4)151
C9—H91⋯O8iv0.932.583.481 (3)162

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

  6 in total

1.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  N-deacetyl ketoconazole-induced hepatotoxicity in a primary culture system of rat hepatocytes.

Authors:  R J Rodriguez; D Acosta
Journal:  Toxicology       Date:  1997-02-28       Impact factor: 4.221

4.  Evaluation of chemicals as inhibitors of trout cytochrome P450s.

Authors:  C L Miranda; M C Henderson; D R Buhler
Journal:  Toxicol Appl Pharmacol       Date:  1998-02       Impact factor: 4.219

5.  Imidazolium 4-amino-benzoate.

Authors:  Rodolfo Moreno-Fuquen; Alan R Kennedy; Denise Gilmour; R H De Almeida Santos; Rommel B Viana
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-11

6.  Imidazolium fumarate.

Authors:  Rodolfo Moreno-Fuquen; Javier Ellena; Jahyr E Theodoro
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-13
  6 in total
  1 in total

1.  Structural characterization of two tetra-chlorido-zincate salts of 4-carb-oxy-1H-imidazol-3-ium: a salt hydrate and a co-crystal salt hydrate.

Authors:  Sean J Martens; David K Geiger
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2017-01-13
  1 in total

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