Literature DB >> 21578933

4-(Dimethyl-amino)pyridinium 2-(4-hydroxy-phenyl-diazen-yl)benzoate.

Hadi D Arman, Tyler Miller, Edward R T Tiekink.   

Abstract

In the title molecular salt, C(7)n class="Species">H(11)N(2) (+)·C(13)H(9)N(2)O(3) (-), the dihedral angle between the benzene rings in the anion is 35.14 (8)°. In the crystal, centrosymmetrically related anions associate via hydrox-yl-carboxyl-ate O-H⋯O hydrogen bonds, resulting in a 24-membered {⋯OC(3)N(2)C(4)OH}(2) synthon. The cations are associated with this dimeric unit via pyridinium-carboxyl-ate N-H⋯O hydrogen bonds. Weak C-H⋯O links further consolidate the packing, generating layers.

Entities:  

Year:  2009        PMID： 21578933      PMCID： PMC2971943          DOI： 10.1107/S1600536809050132

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


Related literature

For a discussion of co-crystal terminology, see: Zukerman-Schpector & Tiekink (2008 ▶). For related co-crystallization studies, see: Broker & Tiekink (2007 ▶); Broker et al. (2008 ▶); Ellis et al. (2009 ▶). For related investigations with 2-(4-hydroxy­phenyl­azo)benzoic acid, see: Corlette & Tiekink (2009 ▶); Arman et al. (2009 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C7H11N2 +·C13n class="Species">H9N2O3 − M = 364.40 Monoclinic, a = 9.240 (4) Å b = 10.924 (4) Å c = 17.598 (7) Å β = 92.002 (8)° V = 1775.2 (12) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 98 K 0.35 × 0.25 × 0.15 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.769, T max = 1 12887 measured reflections 4060 independent reflections 3553 reflections with I > 2σ(I) R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.055 wR(F 2) = 0.135 S = 1.12 4060 reflections 252 parameters 2 restraints H-atom parameters constrained Δρmax = 0.33 e Å−3 Δρmin = −0.32 e Å−3 Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050132/hb5243sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050132/hb5243Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C7H11N2+·C13H9N2O3−F(000) = 768
Mr = 364.40Dx = 1.363 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 7530 reflections
a = 9.240 (4) Åθ = 2.2–40.7°
b = 10.924 (4) ŵ = 0.09 mm−1
c = 17.598 (7) ÅT = 98 K
β = 92.002 (8)°Block, orange
V = 1775.2 (12) Å30.35 × 0.25 × 0.15 mm
Z = 4
Rigaku AFC12K/SATURN724 diffractometer4060 independent reflections
Radiation source: fine-focus sealed tube3553 reflections with I > 2σ(I)
graphiteRint = 0.046
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −11→12
Tmin = 0.769, Tmax = 1k = −14→14
12887 measured reflectionsl = −20→22
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.12w = 1/[σ2(Fo2) + (0.0531P)2 + 0.902P] where P = (Fo2 + 2Fc2)/3
4060 reflections(Δ/σ)max < 0.001
252 parametersΔρmax = 0.33 e Å−3
2 restraintsΔρmin = −0.32 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
O10.52078 (13)0.70075 (11)0.20136 (6)0.0231 (3)
O20.51014 (13)0.74136 (12)0.32532 (6)0.0248 (3)
O30.72197 (13)0.39214 (12)0.69176 (7)0.0252 (3)
H3O0.65070.34460.68710.038*
N10.79272 (15)0.65156 (12)0.37743 (8)0.0198 (3)
N20.86170 (15)0.66758 (13)0.43984 (8)0.0213 (3)
N30.65513 (17)0.60354 (14)0.08591 (8)0.0244 (3)
H3N0.60720.64600.11930.029*
N40.86335 (17)0.38316 (14)−0.06666 (8)0.0253 (3)
C10.73363 (18)0.77410 (15)0.26482 (9)0.0186 (3)
C20.83605 (18)0.73634 (14)0.32047 (9)0.0187 (3)
C30.97934 (18)0.77841 (15)0.31800 (9)0.0210 (3)
H31.05020.74850.35370.025*
C41.01826 (19)0.86322 (16)0.26387 (9)0.0229 (4)
H41.11510.89240.26310.028*
C50.91532 (19)0.90559 (16)0.21068 (9)0.0228 (4)
H50.94060.96620.17480.027*
C60.77532 (18)0.85902 (15)0.21011 (9)0.0206 (3)
H60.70680.88520.17200.025*
C70.57669 (18)0.73456 (14)0.26416 (9)0.0183 (3)
C80.82313 (18)0.58820 (15)0.49950 (9)0.0200 (3)
C90.8914 (2)0.61107 (19)0.56988 (10)0.0318 (4)
H90.96280.67360.57410.038*
C100.8577 (2)0.5449 (2)0.63363 (10)0.0331 (5)
H100.90580.56180.68110.040*
C110.75306 (18)0.45340 (15)0.62834 (9)0.0204 (3)
C120.6840 (2)0.42969 (16)0.55792 (10)0.0248 (4)
H120.61240.36740.55380.030*
C130.7188 (2)0.49608 (16)0.49430 (9)0.0244 (4)
H130.67150.47890.44670.029*
C140.79702 (18)0.45414 (15)−0.01652 (9)0.0213 (3)
C150.82162 (19)0.44292 (16)0.06333 (9)0.0230 (3)
H150.88790.38360.08320.028*
C160.7501 (2)0.51729 (16)0.11111 (10)0.0249 (4)
H160.76750.50840.16440.030*
C170.6284 (2)0.61699 (17)0.01041 (10)0.0261 (4)
H170.56080.6771−0.00710.031*
C180.6963 (2)0.54610 (17)−0.04107 (10)0.0255 (4)
H180.67640.5580−0.09390.031*
C190.8367 (2)0.39889 (19)−0.14862 (10)0.0307 (4)
H19A0.73460.3821−0.16150.046*
H19B0.89780.3419−0.17620.046*
H19C0.85990.4831−0.16300.046*
C200.9618 (2)0.28541 (17)−0.04192 (11)0.0289 (4)
H20A1.05540.3207−0.02580.043*
H20B0.97550.2285−0.08410.043*
H20C0.92070.24140.00080.043*
U11U22U33U12U13U23
O10.0229 (6)0.0285 (6)0.0177 (5)−0.0021 (5)−0.0007 (4)−0.0009 (5)
O20.0268 (6)0.0295 (7)0.0182 (6)−0.0064 (5)0.0033 (5)−0.0022 (5)
O30.0237 (6)0.0323 (7)0.0196 (6)−0.0071 (5)−0.0010 (5)0.0071 (5)
N10.0228 (7)0.0189 (7)0.0177 (6)0.0007 (5)0.0005 (5)0.0003 (5)
N20.0226 (7)0.0223 (7)0.0189 (7)−0.0005 (5)−0.0002 (5)0.0014 (6)
N30.0289 (8)0.0249 (7)0.0194 (7)−0.0001 (6)0.0029 (6)−0.0015 (6)
N40.0280 (8)0.0263 (8)0.0214 (7)0.0064 (6)−0.0031 (6)−0.0024 (6)
C10.0226 (8)0.0186 (7)0.0145 (7)−0.0009 (6)0.0008 (6)−0.0018 (6)
C20.0233 (8)0.0170 (7)0.0157 (7)−0.0012 (6)0.0013 (6)−0.0017 (6)
C30.0224 (8)0.0226 (8)0.0181 (7)−0.0001 (6)0.0002 (6)−0.0014 (6)
C40.0222 (8)0.0256 (8)0.0210 (8)−0.0043 (7)0.0017 (6)−0.0031 (7)
C50.0288 (9)0.0234 (8)0.0163 (7)−0.0045 (7)0.0030 (6)0.0005 (6)
C60.0251 (8)0.0219 (8)0.0146 (7)−0.0021 (6)−0.0009 (6)0.0003 (6)
C70.0213 (8)0.0167 (7)0.0167 (7)−0.0001 (6)0.0006 (6)0.0014 (6)
C80.0216 (8)0.0202 (8)0.0183 (8)0.0001 (6)0.0007 (6)0.0013 (6)
C90.0311 (10)0.0398 (11)0.0241 (9)−0.0168 (8)−0.0049 (7)0.0059 (8)
C100.0337 (10)0.0447 (11)0.0204 (8)−0.0158 (9)−0.0081 (7)0.0069 (8)
C110.0204 (8)0.0226 (8)0.0182 (7)0.0010 (6)0.0013 (6)0.0037 (6)
C120.0306 (9)0.0229 (8)0.0208 (8)−0.0084 (7)−0.0021 (7)0.0005 (7)
C130.0314 (9)0.0244 (8)0.0171 (8)−0.0051 (7)−0.0037 (7)0.0001 (7)
C140.0232 (8)0.0193 (8)0.0211 (8)−0.0010 (6)−0.0005 (6)0.0011 (6)
C150.0262 (9)0.0216 (8)0.0211 (8)−0.0017 (6)−0.0015 (6)0.0049 (7)
C160.0299 (9)0.0256 (8)0.0192 (8)−0.0036 (7)−0.0008 (7)0.0035 (7)
C170.0285 (9)0.0263 (9)0.0234 (8)0.0040 (7)−0.0013 (7)0.0019 (7)
C180.0297 (9)0.0294 (9)0.0172 (8)0.0063 (7)−0.0020 (7)0.0008 (7)
C190.0348 (10)0.0374 (10)0.0200 (8)0.0098 (8)0.0000 (7)−0.0036 (8)
C200.0311 (10)0.0230 (8)0.0325 (9)0.0077 (7)−0.0005 (7)−0.0013 (8)
O1—C71.259 (2)C8—C91.393 (2)
O2—C71.260 (2)C8—C131.394 (2)
O3—C111.341 (2)C9—C101.379 (3)
O3—H3O0.8401C9—H90.9500
N1—N21.263 (2)C10—C111.392 (2)
N1—C21.432 (2)C10—H100.9500
N2—C81.417 (2)C11—C121.398 (2)
N3—C171.351 (2)C12—C131.381 (2)
N3—C161.352 (2)C12—H120.9500
N3—H3N0.8801C13—H130.9500
N4—C141.339 (2)C14—C151.421 (2)
N4—C201.459 (2)C14—C181.426 (2)
N4—C191.465 (2)C15—C161.358 (3)
C1—C21.400 (2)C15—H150.9500
C1—C61.401 (2)C16—H160.9500
C1—C71.513 (2)C17—C181.362 (2)
C2—C31.404 (2)C17—H170.9500
C3—C41.385 (2)C18—H180.9500
C3—H30.9500C19—H19A0.9800
C4—C51.390 (2)C19—H19B0.9800
C4—H40.9500C19—H19C0.9800
C5—C61.390 (2)C20—H20A0.9800
C5—H50.9500C20—H20B0.9800
C6—H60.9500C20—H20C0.9800
C11—O3—H3O114.6C11—C10—H10120.1
N2—N1—C2111.98 (14)O3—C11—C10118.12 (15)
N1—N2—C8115.30 (14)O3—C11—C12122.74 (16)
C17—N3—C16119.54 (15)C10—C11—C12119.15 (15)
C17—N3—H3N121.3C13—C12—C11120.58 (16)
C16—N3—H3N119.0C13—C12—H12119.7
C14—N4—C20121.47 (15)C11—C12—H12119.7
C14—N4—C19121.06 (15)C12—C13—C8120.40 (16)
C20—N4—C19117.45 (15)C12—C13—H13119.8
C2—C1—C6118.72 (15)C8—C13—H13119.8
C2—C1—C7123.06 (14)N4—C14—C15122.72 (16)
C6—C1—C7118.07 (14)N4—C14—C18121.14 (15)
C1—C2—C3119.81 (15)C15—C14—C18116.14 (15)
C1—C2—N1118.78 (15)C16—C15—C14119.77 (16)
C3—C2—N1121.37 (15)C16—C15—H15120.1
C4—C3—C2120.54 (16)C14—C15—H15120.1
C4—C3—H3119.7N3—C16—C15122.57 (16)
C2—C3—H3119.7N3—C16—H16118.7
C3—C4—C5119.84 (16)C15—C16—H16118.7
C3—C4—H4120.1N3—C17—C18121.32 (16)
C5—C4—H4120.1N3—C17—H17119.3
C6—C5—C4119.85 (16)C18—C17—H17119.3
C6—C5—H5120.1C17—C18—C14120.67 (16)
C4—C5—H5120.1C17—C18—H18119.7
C5—C6—C1121.05 (15)C14—C18—H18119.7
C5—C6—H6119.5N4—C19—H19A109.5
C1—C6—H6119.5N4—C19—H19B109.5
O1—C7—O2124.71 (16)H19A—C19—H19B109.5
O1—C7—C1117.02 (14)N4—C19—H19C109.5
O2—C7—C1118.22 (14)H19A—C19—H19C109.5
C9—C8—C13118.59 (16)H19B—C19—H19C109.5
C9—C8—N2115.54 (15)N4—C20—H20A109.5
C13—C8—N2125.76 (15)N4—C20—H20B109.5
C10—C9—C8121.40 (17)H20A—C20—H20B109.5
C10—C9—H9119.3N4—C20—H20C109.5
C8—C9—H9119.3H20A—C20—H20C109.5
C9—C10—C11119.87 (17)H20B—C20—H20C109.5
C9—C10—H10120.1
C2—N1—N2—C8179.04 (13)N2—C8—C9—C10176.36 (19)
C6—C1—C2—C3−3.6 (2)C8—C9—C10—C11−0.2 (3)
C7—C1—C2—C3−179.01 (15)C9—C10—C11—O3−179.18 (18)
C6—C1—C2—N1178.65 (14)C9—C10—C11—C120.2 (3)
C7—C1—C2—N13.2 (2)O3—C11—C12—C13179.40 (17)
N2—N1—C2—C1−148.88 (15)C10—C11—C12—C130.0 (3)
N2—N1—C2—C333.4 (2)C11—C12—C13—C8−0.3 (3)
C1—C2—C3—C44.2 (2)C9—C8—C13—C120.3 (3)
N1—C2—C3—C4−178.05 (15)N2—C8—C13—C12−175.72 (17)
C2—C3—C4—C5−1.1 (2)C20—N4—C14—C152.5 (3)
C3—C4—C5—C6−2.6 (3)C19—N4—C14—C15−179.04 (17)
C4—C5—C6—C13.2 (3)C20—N4—C14—C18−177.34 (17)
C2—C1—C6—C5−0.1 (2)C19—N4—C14—C181.1 (3)
C7—C1—C6—C5175.56 (15)N4—C14—C15—C16−179.58 (17)
C2—C1—C7—O1−134.83 (17)C18—C14—C15—C160.3 (2)
C6—C1—C7—O149.7 (2)C17—N3—C16—C150.4 (3)
C2—C1—C7—O247.4 (2)C14—C15—C16—N3−0.3 (3)
C6—C1—C7—O2−128.09 (17)C16—N3—C17—C18−0.6 (3)
N1—N2—C8—C9−175.62 (16)N3—C17—C18—C140.7 (3)
N1—N2—C8—C130.5 (2)N4—C14—C18—C17179.35 (17)
C13—C8—C9—C10−0.1 (3)C15—C14—C18—C17−0.5 (3)
D—H···AD—HH···AD···AD—H···A
O3—H3o···O2i0.841.772.602 (2)174
N3—H3n···O10.881.782.641 (2)166
C15—H15···O2ii0.952.413.300 (3)157
C19—H19a···O3iii0.982.582.968 (3)103
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O3—H3o⋯O2i 0.841.772.602 (2)174
N3—H3n⋯O10.881.782.641 (2)166
C15—H15⋯O2ii 0.952.413.300 (3)157
C19—H19a⋯O3iii 0.982.582.968 (3)103

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

  2 in total

1.  A short history of SHELX.

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

2.  2-[(4-Hydroxy-phen-yl)diazen-yl]benzoic acid-N,N'-bis-(4-pyridylmeth-yl)oxamide (2/1).

Authors:  Hadi D Arman; Tyler Miller; Pavel Poplaukhin; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-21
  2 in total

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