Acta Cryst. (2009). E65, o1205 [ doi:10.1107/S1600536809016043 ]
In the title 1:1 adduct, C7H6O3·C3H4N2, the crystal packing features ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking interactions [centroid-centroid distances = 3.799 (2) and 3.753 (1) Å] as well as N-H
(O,O) O-HO and C-HO hydrogen bonds.
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.
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.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
![[Figure 1]](./at2768fig1thm.gif)
| Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme. |
| C7H6O3·C3H4N2 | F(000) = 440 |
| Mr = 206.20 | Dx = 1.398 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 2125 reflections |
| a = 9.601 (2) Å | θ = 2.9–25.6° |
| b = 10.530 (2) Å | µ = 0.11 mm−1 |
| c = 10.586 (2) Å | T = 293 K |
| β = 113.759 (3)° | Block, colourless |
| V = 979.6 (4) Å3 | 0.47 × 0.29 × 0.10 mm |
| Z = 4 |
| Siemens SMART 1000 CCD area-detector diffractometer | 1858 independent reflections |
| Radiation source: fine-focus sealed tube | 1583 reflections with I > 2σ(I) |
| graphite | Rint = 0.024 |
| Detector resolution: 8.33 pixels mm-1 | θmax = 25.7°, θmin = 2.4° |
| ω scans | h = −10→11 |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→12 |
| Tmin = 0.955, Tmax = 0.987 | l = −12→5 |
| 5200 measured reflections |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.213 | H-atom parameters constrained |
| S = 1.11 | w = 1/[σ2(Fo2) + (0.1212P)2 + 0.6043P] where P = (Fo2 + 2Fc2)/3 |
| 1858 reflections | (Δ/σ)max < 0.001 |
| 136 parameters | Δρmax = 0.61 e Å−3 |
| 0 restraints | Δρmin = −0.47 e Å−3 |
| C7H6O3·C3H4N2 | V = 979.6 (4) Å3 |
| Mr = 206.20 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 9.601 (2) Å | µ = 0.11 mm−1 |
| b = 10.530 (2) Å | T = 293 K |
| c = 10.586 (2) Å | 0.47 × 0.29 × 0.10 mm |
| β = 113.759 (3)° |
| Siemens SMART 1000 CCD area-detector diffractometer | 1858 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1583 reflections with I > 2σ(I) |
| Tmin = 0.955, Tmax = 0.987 | Rint = 0.024 |
| 5200 measured reflections | θmax = 25.7° |
| R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
| wR(F2) = 0.213 | Δρmax = 0.61 e Å−3 |
| S = 1.11 | Δρmin = −0.47 e Å−3 |
| 1858 reflections | Absolute structure: ? |
| 136 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | −0.0067 (2) | 0.60204 (17) | 0.30887 (18) | 0.0406 (5) | |
| O2 | 0.1226 (2) | 0.62774 (19) | 0.53341 (19) | 0.0494 (6) | |
| H2 | 0.1995 | 0.5993 | 0.5951 | 0.080* | |
| C1 | 0.2147 (3) | 0.4753 (2) | 0.4208 (2) | 0.0376 (6) | |
| N1 | −0.0869 (3) | 0.8121 (2) | 0.4675 (2) | 0.0444 (6) | |
| H1 | −0.0212 | 0.7516 | 0.4899 | 0.080* | |
| C10 | 0.1036 (3) | 0.5752 (2) | 0.4219 (3) | 0.0361 (6) | |
| O3 | 0.5211 (3) | 0.1947 (2) | 0.4273 (2) | 0.0614 (7) | |
| H3 | 0.5014 | 0.1663 | 0.3499 | 0.080* | |
| C2 | 0.2031 (3) | 0.4185 (3) | 0.2978 (3) | 0.0421 (7) | |
| H2A | 0.1256 | 0.4433 | 0.2149 | 0.080* | |
| C8 | −0.2648 (3) | 0.9398 (2) | 0.3478 (3) | 0.0364 (6) | |
| H8 | −0.3401 | 0.9793 | 0.2727 | 0.080* | |
| C7 | −0.1811 (3) | 0.8415 (3) | 0.3413 (3) | 0.0461 (7) | |
| H7 | −0.1880 | 0.8005 | 0.2611 | 0.080* | |
| C4 | 0.4199 (3) | 0.2872 (3) | 0.4201 (3) | 0.0438 (7) | |
| C6 | 0.3317 (3) | 0.4363 (3) | 0.5424 (3) | 0.0478 (7) | |
| H6 | 0.3420 | 0.4738 | 0.6253 | 0.080* | |
| C3 | 0.3048 (3) | 0.3260 (3) | 0.2973 (3) | 0.0449 (7) | |
| H3A | 0.2960 | 0.2896 | 0.2143 | 0.080* | |
| C5 | 0.4330 (4) | 0.3435 (3) | 0.5433 (3) | 0.0545 (8) | |
| H5 | 0.5102 | 0.3183 | 0.6262 | 0.080* | |
| 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 | −0.0586 | 0.8941 | 0.6528 | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0403 (10) | 0.0418 (10) | 0.0347 (10) | 0.0012 (7) | 0.0099 (8) | 0.0032 (7) |
| O2 | 0.0488 (11) | 0.0549 (12) | 0.0346 (10) | 0.0151 (9) | 0.0065 (8) | −0.0054 (8) |
| C1 | 0.0384 (13) | 0.0386 (13) | 0.0336 (13) | −0.0009 (10) | 0.0121 (11) | −0.0003 (10) |
| N1 | 0.0458 (12) | 0.0424 (12) | 0.0412 (13) | 0.0075 (10) | 0.0137 (10) | 0.0059 (10) |
| C10 | 0.0366 (13) | 0.0371 (13) | 0.0319 (13) | −0.0023 (10) | 0.0108 (10) | 0.0022 (9) |
| O3 | 0.0610 (13) | 0.0710 (15) | 0.0436 (12) | 0.0277 (11) | 0.0122 (10) | −0.0073 (10) |
| C2 | 0.0438 (14) | 0.0463 (14) | 0.0319 (13) | 0.0046 (11) | 0.0109 (11) | 0.0005 (10) |
| C8 | 0.0331 (12) | 0.0372 (12) | 0.0323 (12) | 0.0079 (10) | 0.0065 (10) | 0.0097 (10) |
| C7 | 0.0475 (15) | 0.0476 (15) | 0.0386 (14) | 0.0003 (12) | 0.0125 (12) | −0.0002 (12) |
| C4 | 0.0435 (14) | 0.0466 (15) | 0.0398 (14) | 0.0068 (11) | 0.0154 (12) | −0.0027 (11) |
| C6 | 0.0517 (16) | 0.0551 (16) | 0.0305 (13) | 0.0116 (13) | 0.0101 (12) | −0.0063 (11) |
| C3 | 0.0498 (15) | 0.0503 (15) | 0.0327 (13) | 0.0049 (12) | 0.0146 (12) | −0.0052 (11) |
| C5 | 0.0527 (16) | 0.0673 (19) | 0.0316 (14) | 0.0177 (14) | 0.0048 (12) | −0.0024 (13) |
| N2 | 0.075 (2) | 0.0681 (19) | 0.075 (2) | 0.0103 (15) | 0.0332 (17) | 0.0024 (15) |
| C9 | 0.0572 (17) | 0.0594 (18) | 0.0343 (15) | 0.0063 (14) | 0.0137 (13) | 0.0022 (12) |
| O1—C10 | 1.269 (3) | C8—C7 | 1.330 (4) |
| O2—C10 | 1.249 (3) | C8—N2 | 1.358 (4) |
| O2—H2 | 0.8200 | C8—H8 | 0.9300 |
| C1—C6 | 1.387 (4) | C7—H7 | 0.9300 |
| C1—C2 | 1.396 (4) | C4—C3 | 1.386 (4) |
| C1—C10 | 1.502 (4) | C4—C5 | 1.391 (4) |
| N1—C7 | 1.313 (4) | C6—C5 | 1.376 (4) |
| N1—C9 | 1.367 (4) | C6—H6 | 0.9300 |
| N1—H1 | 0.8600 | C3—H3A | 0.9300 |
| O3—C4 | 1.357 (3) | C5—H5 | 0.9300 |
| O3—H3 | 0.8200 | N2—C9 | 1.341 (4) |
| C2—C3 | 1.381 (4) | C9—H9 | 0.9300 |
| C2—H2A | 0.9300 | ||
| C10—O2—H2 | 109.5 | N1—C7—H7 | 125.9 |
| C6—C1—C2 | 118.0 (2) | C8—C7—H7 | 125.9 |
| C6—C1—C10 | 120.8 (2) | O3—C4—C3 | 123.1 (2) |
| C2—C1—C10 | 121.2 (2) | O3—C4—C5 | 117.4 (2) |
| C7—N1—C9 | 108.7 (2) | C3—C4—C5 | 119.4 (2) |
| C7—N1—H1 | 125.7 | C5—C6—C1 | 121.5 (2) |
| C9—N1—H1 | 125.7 | C5—C6—H6 | 119.3 |
| O2—C10—O1 | 122.8 (2) | C1—C6—H6 | 119.3 |
| O2—C10—C1 | 118.9 (2) | C2—C3—C4 | 120.1 (2) |
| O1—C10—C1 | 118.3 (2) | C2—C3—H3A | 119.9 |
| C4—O3—H3 | 109.5 | C4—C3—H3A | 119.9 |
| C3—C2—C1 | 121.0 (2) | C6—C5—C4 | 119.9 (3) |
| C3—C2—H2A | 119.5 | C6—C5—H5 | 120.0 |
| C1—C2—H2A | 119.5 | C4—C5—H5 | 120.0 |
| C7—C8—N2 | 108.9 (2) | C9—N2—C8 | 106.8 (3) |
| C7—C8—H8 | 125.6 | N2—C9—N1 | 107.3 (3) |
| N2—C8—H8 | 125.6 | N2—C9—H9 | 126.3 |
| N1—C7—C8 | 108.2 (2) | N1—C9—H9 | 126.3 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1 | 0.86 | 2.527 | 3.057 (3) | 120.73 |
| N1—H1···O2 | 0.86 | 1.818 | 2.678 (3) | 177.32 |
| O3—H3···O1i | 0.82 | 1.831 | 2.635 (3) | 166.35 |
| C8—H8···O1ii | 0.93 | 1.886 | 2.748 (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. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1 | 0.86 | 2.527 | 3.057 (3) | 120.73 |
| N1—H1···O2 | 0.86 | 1.818 | 2.678 (3) | 177.32 |
| O3—H3···O1i | 0.82 | 1.831 | 2.635 (3) | 166.35 |
| C8—H8···O1ii | 0.93 | 1.886 | 2.748 (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. |
This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Y2008B02 and Y2008B32).
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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).