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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1205.
Published online 2009 May 7. doi:  10.1107/S1600536809016043
PMCID: PMC2969827

4-Hydroxy­benzoic acid–1H-imidazole (1/1)

Abstract

In the title 1:1 adduct, C7H6O3·C3H4N2, the crystal packing features π–π stacking inter­actions [centroid–centroid distances = 3.799 (2) and 3.753 (1) Å] as well as N—H(...)(O,O) O—H(...)O and C—H(...)O hydrogen bonds.

Related literature

For related structures, see: Li et al. (2005 [triangle]); Wan et al. (2005 [triangle]). For the synthesis, see: Wang et al. (2006 [triangle]). For bond-length data, see Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1205-scheme1.jpg

Experimental

Crystal data

  • C7H6O3·C3H4N2
  • M r = 206.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1205-efi1.jpg
  • a = 9.601 (2) Å
  • b = 10.530 (2) Å
  • c = 10.586 (2) Å
  • β = 113.759 (3)°
  • V = 979.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 293 K
  • 0.47 × 0.29 × 0.10 mm

Data collection

  • Siemens SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.955, T max = 0.987
  • 5200 measured reflections
  • 1858 independent reflections
  • 1583 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.213
  • S = 1.11
  • 1858 reflections
  • 136 parameters
  • H-atom parameters constrained
  • Δρmax = 0.61 e Å−3
  • Δρmin = −0.47 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016043/at2768sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016043/at2768Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This project was supported by the Natural Science Found­ation of Shandong Province (grant Nos. Y2008B02 and Y2008B32).

supplementary crystallographic information

Comment

Imidazole compounds have received considerable attention in the literature. We have reported the structure of 3-(1H-imidazol-1-yl)-1-phenylpropan-1-one, (II) (Li et al., 2005). In order to obtain comprehensive structural information of imidazole compounds and in our ongoing search for new imidazole compounds, the title compound, (I), was prepared hydrothermally and we report its structure here.

A view of the molecule of the title compound, (I), is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The bonds in the imidazole and hydroxybenzoate systems show intermediate character between single and double bonds, indicating a highly π-conjugated delocalization. The crystal structure is stabilized by π–π interactions involving the imidazole and hydroxybenzoate rings: Cg1···Cg1 (-x, 2 - y, 1 - z) = 3.799 Å and Cg1···Cg2 (-x, 1 - y, 1 - z) = 3.753 Å, where Cg1 and Cg2 denote the centroids of the N1/N2/C7—C9 imidazole and C1—C6 benzene rings, respectively. In the crystal packing, molecules are linked into three-dimension network by C—H···O and O—H···O intermolecular hydrogen bonds (Table 1).

Experimental

The title compound was prepared according to the literature method of Wang et al. (2006). It was hydrothermally prepared from a reaction mixture of CdCl2.2.5H2O, 4-hydroxybenzoic acid, 1H-imidazole, and distilled water (10 ml) in a molar ratio of 1:2:6:555. The mixture was stirred for 20 min at room temperature and then crystallized in a Teflon-lined stainless steel autoclave with a 23 ml capacity at 433 K for five days. After cooling, single crystals of (I) suitable for X-ray measurements were obtained.

Refinement

All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H = 0.93–0.96 Å, O—H = 0.82 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2 Ueq(C,N) or 1.5 Ueq(O) for hydroxy H atoms.

Figures

Fig. 1.
The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.

Crystal data

C7H6O3·C3H4N2F(000) = 440
Mr = 206.20Dx = 1.398 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2125 reflections
a = 9.601 (2) Åθ = 2.9–25.6°
b = 10.530 (2) ŵ = 0.11 mm1
c = 10.586 (2) ÅT = 293 K
β = 113.759 (3)°Block, colourless
V = 979.6 (4) Å30.47 × 0.29 × 0.10 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer1858 independent reflections
Radiation source: fine-focus sealed tube1583 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 8.33 pixels mm-1θmax = 25.7°, θmin = 2.4°
ω scansh = −10→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −12→12
Tmin = 0.955, Tmax = 0.987l = −12→5
5200 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.1212P)2 + 0.6043P] where P = (Fo2 + 2Fc2)/3
1858 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = −0.47 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1−0.0067 (2)0.60204 (17)0.30887 (18)0.0406 (5)
O20.1226 (2)0.62774 (19)0.53341 (19)0.0494 (6)
H20.19950.59930.59510.080*
C10.2147 (3)0.4753 (2)0.4208 (2)0.0376 (6)
N1−0.0869 (3)0.8121 (2)0.4675 (2)0.0444 (6)
H1−0.02120.75160.48990.080*
C100.1036 (3)0.5752 (2)0.4219 (3)0.0361 (6)
O30.5211 (3)0.1947 (2)0.4273 (2)0.0614 (7)
H30.50140.16630.34990.080*
C20.2031 (3)0.4185 (3)0.2978 (3)0.0421 (7)
H2A0.12560.44330.21490.080*
C8−0.2648 (3)0.9398 (2)0.3478 (3)0.0364 (6)
H8−0.34010.97930.27270.080*
C7−0.1811 (3)0.8415 (3)0.3413 (3)0.0461 (7)
H7−0.18800.80050.26110.080*
C40.4199 (3)0.2872 (3)0.4201 (3)0.0438 (7)
C60.3317 (3)0.4363 (3)0.5424 (3)0.0478 (7)
H60.34200.47380.62530.080*
C30.3048 (3)0.3260 (3)0.2973 (3)0.0449 (7)
H3A0.29600.28960.21430.080*
C50.4330 (4)0.3435 (3)0.5433 (3)0.0545 (8)
H50.51020.31830.62620.080*
N2−0.2226 (4)0.9731 (3)0.4821 (3)0.0715 (9)
C9−0.1105 (4)0.8937 (3)0.5572 (3)0.0519 (8)
H9−0.05860.89410.65280.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0403 (10)0.0418 (10)0.0347 (10)0.0012 (7)0.0099 (8)0.0032 (7)
O20.0488 (11)0.0549 (12)0.0346 (10)0.0151 (9)0.0065 (8)−0.0054 (8)
C10.0384 (13)0.0386 (13)0.0336 (13)−0.0009 (10)0.0121 (11)−0.0003 (10)
N10.0458 (12)0.0424 (12)0.0412 (13)0.0075 (10)0.0137 (10)0.0059 (10)
C100.0366 (13)0.0371 (13)0.0319 (13)−0.0023 (10)0.0108 (10)0.0022 (9)
O30.0610 (13)0.0710 (15)0.0436 (12)0.0277 (11)0.0122 (10)−0.0073 (10)
C20.0438 (14)0.0463 (14)0.0319 (13)0.0046 (11)0.0109 (11)0.0005 (10)
C80.0331 (12)0.0372 (12)0.0323 (12)0.0079 (10)0.0065 (10)0.0097 (10)
C70.0475 (15)0.0476 (15)0.0386 (14)0.0003 (12)0.0125 (12)−0.0002 (12)
C40.0435 (14)0.0466 (15)0.0398 (14)0.0068 (11)0.0154 (12)−0.0027 (11)
C60.0517 (16)0.0551 (16)0.0305 (13)0.0116 (13)0.0101 (12)−0.0063 (11)
C30.0498 (15)0.0503 (15)0.0327 (13)0.0049 (12)0.0146 (12)−0.0052 (11)
C50.0527 (16)0.0673 (19)0.0316 (14)0.0177 (14)0.0048 (12)−0.0024 (13)
N20.075 (2)0.0681 (19)0.075 (2)0.0103 (15)0.0332 (17)0.0024 (15)
C90.0572 (17)0.0594 (18)0.0343 (15)0.0063 (14)0.0137 (13)0.0022 (12)

Geometric parameters (Å, °)

O1—C101.269 (3)C8—C71.330 (4)
O2—C101.249 (3)C8—N21.358 (4)
O2—H20.8200C8—H80.9300
C1—C61.387 (4)C7—H70.9300
C1—C21.396 (4)C4—C31.386 (4)
C1—C101.502 (4)C4—C51.391 (4)
N1—C71.313 (4)C6—C51.376 (4)
N1—C91.367 (4)C6—H60.9300
N1—H10.8600C3—H3A0.9300
O3—C41.357 (3)C5—H50.9300
O3—H30.8200N2—C91.341 (4)
C2—C31.381 (4)C9—H90.9300
C2—H2A0.9300
C10—O2—H2109.5N1—C7—H7125.9
C6—C1—C2118.0 (2)C8—C7—H7125.9
C6—C1—C10120.8 (2)O3—C4—C3123.1 (2)
C2—C1—C10121.2 (2)O3—C4—C5117.4 (2)
C7—N1—C9108.7 (2)C3—C4—C5119.4 (2)
C7—N1—H1125.7C5—C6—C1121.5 (2)
C9—N1—H1125.7C5—C6—H6119.3
O2—C10—O1122.8 (2)C1—C6—H6119.3
O2—C10—C1118.9 (2)C2—C3—C4120.1 (2)
O1—C10—C1118.3 (2)C2—C3—H3A119.9
C4—O3—H3109.5C4—C3—H3A119.9
C3—C2—C1121.0 (2)C6—C5—C4119.9 (3)
C3—C2—H2A119.5C6—C5—H5120.0
C1—C2—H2A119.5C4—C5—H5120.0
C7—C8—N2108.9 (2)C9—N2—C8106.8 (3)
C7—C8—H8125.6N2—C9—N1107.3 (3)
N2—C8—H8125.6N2—C9—H9126.3
N1—C7—C8108.2 (2)N1—C9—H9126.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.5273.057 (3)120.73
N1—H1···O20.861.8182.678 (3)177.32
O3—H3···O1i0.821.8312.635 (3)166.35
C8—H8···O1ii0.931.8862.748 (3)153.18

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x−1/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2768).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Li, X.-M., Wan, J., Zhang, S.-S. & Ouyang, P.-K. (2005). Acta Cryst. E61, o3632–o3633.
  • Nardelli, M. (1995). J. Appl. Cryst.28, 659.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments, Inc., Madison, Wisconsin, USA.
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Wan, J., Peng, Z.-Z., Li, X.-M., Ouyang, P.-K. & Zhang, S.-S. (2005). Acta Cryst. E61, o2585–o2586.
  • Wang, L., Yang, M., Li, G.-H., Shi, Z. & Feng, S.-H. (2006). Inorg. Chem.45, 2474–2478. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography