Acta Cryst. (2009). E65, o2164 [ doi:10.1107/S1600536809031894 ]
In the title molecule, C15H17N3O5, the dihedral angle between the benzene and imidazole rings is 3.69 (2)°. The crystal structure is stabilized by weak intermolecular C-H
O hydrogen bonds and ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking interactions with a centroid-centroid distance of 3.614 (1) Å.
Compound (I) was synthesized according to the procedure of Khalafi-Nezhad et al. (2005). Single crystals used in X-ray diffraction studies were grown by slow evaporation at room temperature of solutions of (I) in ethyl acetate and dichlormethane mixtures.
Hydrogen atoms were placed in calculated positions with C—H = 0.95Å (aromatic), 0.99Å (methylene) and 0.98Å (methyl) with Uiso(H) = 1.2Ueq(C) (aromatic and methylene C) or 1.5Ueq(C) (methyl C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./lh2876fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
| C15H17N3O5 | F(000) = 672 |
| Mr = 319.32 | Dx = 1.370 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 3149 reflections |
| a = 9.4885 (14) Å | θ = 2.3–26.9° |
| b = 13.048 (2) Å | µ = 0.10 mm−1 |
| c = 12.745 (2) Å | T = 173 K |
| β = 101.120 (3)° | Block, colorless |
| V = 1548.3 (4) Å3 | 0.28 × 0.24 × 0.2 mm |
| Z = 4 |
| Bruker SMART CCD diffractometer | 3329 independent reflections |
| Radiation source: fine-focus sealed tube | 2329 reflections with I > 2σ(I) |
| graphite | Rint = 0.022 |
| φ and ω scans | θmax = 27.0°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→12 |
| Tmin = 0.971, Tmax = 0.979 | k = −15→16 |
| 7761 measured reflections | l = −13→16 |
| 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.130 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0623P)2 + 0.3992P] where P = (Fo2 + 2Fc2)/3 |
| 3329 reflections | (Δ/σ)max < 0.001 |
| 210 parameters | Δρmax = 0.27 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| C15H17N3O5 | V = 1548.3 (4) Å3 |
| Mr = 319.32 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 9.4885 (14) Å | µ = 0.10 mm−1 |
| b = 13.048 (2) Å | T = 173 K |
| c = 12.745 (2) Å | 0.28 × 0.24 × 0.2 mm |
| β = 101.120 (3)° |
| Bruker SMART CCD diffractometer | 3329 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2329 reflections with I > 2σ(I) |
| Tmin = 0.971, Tmax = 0.979 | Rint = 0.022 |
| 7761 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.130 | Δρmax = 0.27 e Å−3 |
| S = 1.03 | Δρmin = −0.19 e Å−3 |
| 3329 reflections | Absolute structure: ? |
| 210 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 | ||
| C1 | 0.2645 (2) | 1.03088 (14) | −0.03024 (16) | 0.0502 (5) | |
| H1 | 0.2344 | 1.0901 | 0.0028 | 0.060* | |
| C2 | 0.21471 (17) | 0.93177 (12) | 0.00141 (13) | 0.0363 (4) | |
| C3 | 0.25719 (18) | 0.84045 (12) | −0.04102 (14) | 0.0381 (4) | |
| H3 | 0.3193 | 0.8421 | −0.0912 | 0.046* | |
| C4 | 0.3482 (2) | 0.65169 (17) | −0.1102 (2) | 0.0691 (7) | |
| H4A | 0.3107 | 0.6882 | −0.1769 | 0.104* | |
| H4B | 0.3681 | 0.5803 | −0.1262 | 0.104* | |
| H4C | 0.4370 | 0.6847 | −0.0737 | 0.104* | |
| C5 | 0.20870 (17) | 0.74857 (12) | −0.00975 (13) | 0.0346 (4) | |
| C6 | 0.11391 (16) | 0.74686 (11) | 0.06315 (12) | 0.0305 (3) | |
| C7 | 0.07388 (17) | 0.83703 (11) | 0.10519 (13) | 0.0322 (4) | |
| H7 | 0.0114 | 0.8359 | 0.1551 | 0.039* | |
| C8 | 0.12529 (17) | 0.92983 (12) | 0.07433 (13) | 0.0347 (4) | |
| H8 | 0.0985 | 0.9921 | 0.1038 | 0.042* | |
| C9 | −0.01627 (18) | 0.64126 (12) | 0.16566 (14) | 0.0360 (4) | |
| H9A | −0.1090 | 0.6775 | 0.1440 | 0.043* | |
| H9B | 0.0344 | 0.6699 | 0.2346 | 0.043* | |
| C10 | −0.04042 (17) | 0.52728 (12) | 0.17563 (14) | 0.0378 (4) | |
| H10A | −0.1107 | 0.5152 | 0.2225 | 0.045* | |
| H10B | −0.0800 | 0.4981 | 0.1043 | 0.045* | |
| C11 | 0.0990 (2) | 0.47573 (13) | 0.2218 (2) | 0.0616 (6) | |
| H11A | 0.1721 | 0.4966 | 0.1802 | 0.074* | |
| H11B | 0.1316 | 0.4999 | 0.2962 | 0.074* | |
| C12 | 0.16148 (17) | 0.29675 (13) | 0.16772 (13) | 0.0384 (4) | |
| C13 | 0.2589 (2) | 0.33135 (16) | 0.09670 (16) | 0.0560 (5) | |
| H13A | 0.2936 | 0.2717 | 0.0624 | 0.084* | |
| H13B | 0.3407 | 0.3680 | 0.1390 | 0.084* | |
| H13C | 0.2066 | 0.3772 | 0.0417 | 0.084* | |
| C14 | 0.01304 (17) | 0.30668 (12) | 0.28026 (15) | 0.0403 (4) | |
| H14 | −0.0475 | 0.3304 | 0.3264 | 0.048* | |
| C15 | 0.04200 (16) | 0.20834 (11) | 0.25747 (13) | 0.0326 (4) | |
| N1 | 0.09014 (14) | 0.36345 (10) | 0.22222 (12) | 0.0417 (4) | |
| N2 | 0.13429 (14) | 0.20076 (10) | 0.18821 (11) | 0.0346 (3) | |
| N3 | −0.01634 (15) | 0.11998 (11) | 0.29957 (12) | 0.0404 (4) | |
| O1 | 0.34061 (19) | 1.04390 (12) | −0.09476 (13) | 0.0758 (5) | |
| O2 | 0.24432 (13) | 0.65445 (9) | −0.04271 (11) | 0.0493 (4) | |
| O3 | 0.06945 (12) | 0.65190 (8) | 0.08547 (10) | 0.0376 (3) | |
| O4 | 0.02197 (15) | 0.03485 (9) | 0.27613 (12) | 0.0544 (4) | |
| O5 | −0.10418 (15) | 0.13411 (11) | 0.35800 (12) | 0.0611 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0631 (12) | 0.0379 (10) | 0.0515 (11) | −0.0115 (8) | 0.0156 (10) | 0.0021 (8) |
| C2 | 0.0422 (9) | 0.0306 (8) | 0.0360 (9) | −0.0055 (7) | 0.0074 (7) | 0.0004 (7) |
| C3 | 0.0385 (9) | 0.0378 (9) | 0.0404 (9) | −0.0086 (7) | 0.0139 (7) | −0.0058 (7) |
| C4 | 0.0556 (12) | 0.0577 (13) | 0.1071 (19) | −0.0074 (10) | 0.0486 (13) | −0.0360 (13) |
| C5 | 0.0327 (8) | 0.0294 (8) | 0.0427 (9) | −0.0027 (6) | 0.0097 (7) | −0.0106 (7) |
| C6 | 0.0306 (8) | 0.0248 (7) | 0.0355 (8) | −0.0027 (6) | 0.0046 (6) | −0.0010 (6) |
| C7 | 0.0370 (8) | 0.0285 (8) | 0.0327 (8) | 0.0011 (6) | 0.0106 (7) | −0.0008 (6) |
| C8 | 0.0420 (9) | 0.0249 (8) | 0.0365 (9) | 0.0012 (6) | 0.0057 (7) | −0.0022 (6) |
| C9 | 0.0391 (9) | 0.0279 (8) | 0.0435 (9) | −0.0007 (7) | 0.0140 (7) | 0.0017 (7) |
| C10 | 0.0375 (9) | 0.0284 (8) | 0.0483 (10) | −0.0015 (7) | 0.0106 (7) | 0.0036 (7) |
| C11 | 0.0487 (11) | 0.0249 (9) | 0.0984 (17) | −0.0025 (8) | −0.0175 (11) | 0.0050 (9) |
| C12 | 0.0367 (8) | 0.0364 (9) | 0.0391 (9) | −0.0067 (7) | −0.0004 (7) | 0.0046 (7) |
| C13 | 0.0567 (12) | 0.0595 (12) | 0.0517 (12) | −0.0214 (10) | 0.0102 (10) | 0.0122 (10) |
| C14 | 0.0356 (8) | 0.0316 (9) | 0.0529 (11) | 0.0045 (7) | 0.0065 (8) | −0.0035 (8) |
| C15 | 0.0321 (8) | 0.0273 (8) | 0.0384 (9) | 0.0018 (6) | 0.0068 (7) | 0.0007 (6) |
| N1 | 0.0360 (8) | 0.0254 (7) | 0.0597 (10) | −0.0008 (6) | −0.0008 (7) | 0.0048 (6) |
| N2 | 0.0368 (7) | 0.0309 (7) | 0.0370 (7) | −0.0023 (6) | 0.0092 (6) | 0.0003 (6) |
| N3 | 0.0445 (8) | 0.0319 (7) | 0.0494 (9) | 0.0022 (6) | 0.0202 (7) | 0.0034 (6) |
| O1 | 0.1041 (12) | 0.0577 (9) | 0.0781 (11) | −0.0285 (9) | 0.0487 (10) | 0.0027 (8) |
| O2 | 0.0480 (7) | 0.0329 (7) | 0.0749 (9) | −0.0048 (5) | 0.0318 (7) | −0.0182 (6) |
| O3 | 0.0431 (6) | 0.0236 (6) | 0.0494 (7) | −0.0037 (5) | 0.0176 (5) | −0.0026 (5) |
| O4 | 0.0732 (9) | 0.0259 (6) | 0.0739 (9) | 0.0032 (6) | 0.0383 (7) | 0.0049 (6) |
| O5 | 0.0638 (9) | 0.0543 (8) | 0.0784 (10) | 0.0023 (7) | 0.0471 (8) | 0.0018 (7) |
| C1—O1 | 1.207 (2) | C9—H9B | 0.9900 |
| C1—C2 | 1.460 (2) | C10—C11 | 1.499 (2) |
| C1—H1 | 0.9500 | C10—H10A | 0.9900 |
| C2—C8 | 1.374 (2) | C10—H10B | 0.9900 |
| C2—C3 | 1.400 (2) | C11—N1 | 1.468 (2) |
| C3—C5 | 1.371 (2) | C11—H11A | 0.9900 |
| C3—H3 | 0.9500 | C11—H11B | 0.9900 |
| C4—O2 | 1.428 (2) | C12—N2 | 1.315 (2) |
| C4—H4A | 0.9800 | C12—N1 | 1.371 (2) |
| C4—H4B | 0.9800 | C12—C13 | 1.483 (2) |
| C4—H4C | 0.9800 | C13—H13A | 0.9800 |
| C5—O2 | 1.3615 (18) | C13—H13B | 0.9800 |
| C5—C6 | 1.412 (2) | C13—H13C | 0.9800 |
| C6—O3 | 1.3567 (18) | C14—C15 | 1.355 (2) |
| C6—C7 | 1.376 (2) | C14—N1 | 1.356 (2) |
| C7—C8 | 1.390 (2) | C14—H14 | 0.9500 |
| C7—H7 | 0.9500 | C15—N2 | 1.362 (2) |
| C8—H8 | 0.9500 | C15—N3 | 1.428 (2) |
| C9—O3 | 1.4304 (19) | N3—O4 | 1.2235 (17) |
| C9—C10 | 1.514 (2) | N3—O5 | 1.2339 (18) |
| C9—H9A | 0.9900 | ||
| O1—C1—C2 | 125.53 (19) | C9—C10—H10A | 109.7 |
| O1—C1—H1 | 117.2 | C11—C10—H10B | 109.7 |
| C2—C1—H1 | 117.2 | C9—C10—H10B | 109.7 |
| C8—C2—C3 | 120.47 (14) | H10A—C10—H10B | 108.2 |
| C8—C2—C1 | 118.55 (15) | N1—C11—C10 | 113.74 (14) |
| C3—C2—C1 | 120.98 (16) | N1—C11—H11A | 108.8 |
| C5—C3—C2 | 119.63 (15) | C10—C11—H11A | 108.8 |
| C5—C3—H3 | 120.2 | N1—C11—H11B | 108.8 |
| C2—C3—H3 | 120.2 | C10—C11—H11B | 108.8 |
| O2—C4—H4A | 109.5 | H11A—C11—H11B | 107.7 |
| O2—C4—H4B | 109.5 | N2—C12—N1 | 111.65 (15) |
| H4A—C4—H4B | 109.5 | N2—C12—C13 | 125.48 (17) |
| O2—C4—H4C | 109.5 | N1—C12—C13 | 122.86 (16) |
| H4A—C4—H4C | 109.5 | C12—C13—H13A | 109.5 |
| H4B—C4—H4C | 109.5 | C12—C13—H13B | 109.5 |
| O2—C5—C3 | 125.59 (15) | H13A—C13—H13B | 109.5 |
| O2—C5—C6 | 114.59 (14) | C12—C13—H13C | 109.5 |
| C3—C5—C6 | 119.82 (14) | H13A—C13—H13C | 109.5 |
| O3—C6—C7 | 125.37 (14) | H13B—C13—H13C | 109.5 |
| O3—C6—C5 | 114.55 (13) | C15—C14—N1 | 104.31 (15) |
| C7—C6—C5 | 120.08 (14) | C15—C14—H14 | 127.8 |
| C6—C7—C8 | 119.74 (14) | N1—C14—H14 | 127.8 |
| C6—C7—H7 | 120.1 | C14—C15—N2 | 112.96 (14) |
| C8—C7—H7 | 120.1 | C14—C15—N3 | 125.07 (15) |
| C2—C8—C7 | 120.23 (14) | N2—C15—N3 | 121.97 (13) |
| C2—C8—H8 | 119.9 | C14—N1—C12 | 107.49 (13) |
| C7—C8—H8 | 119.9 | C14—N1—C11 | 125.74 (17) |
| O3—C9—C10 | 105.75 (12) | C12—N1—C11 | 126.73 (16) |
| O3—C9—H9A | 110.6 | C12—N2—C15 | 103.59 (13) |
| C10—C9—H9A | 110.6 | O4—N3—O5 | 123.37 (14) |
| O3—C9—H9B | 110.6 | O4—N3—C15 | 119.10 (13) |
| C10—C9—H9B | 110.6 | O5—N3—C15 | 117.52 (13) |
| H9A—C9—H9B | 108.7 | C5—O2—C4 | 116.73 (14) |
| C11—C10—C9 | 109.72 (14) | C6—O3—C9 | 118.76 (12) |
| C11—C10—H10A | 109.7 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4B···O4i | 0.98 | 2.58 | 3.415 (3) | 144 |
| C8—H8···O4ii | 0.95 | 2.51 | 3.229 (2) | 133 |
| C10—H10B···O2iii | 0.99 | 2.56 | 3.312 (2) | 133 |
| C10—H10A···O1iv | 0.99 | 2.58 | 3.461 (2) | 148 |
| C14—H14···O1iv | 0.95 | 2.29 | 3.166 (2) | 153 |
| Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x, y+1, z; (iii) −x, −y+1, −z; (iv) x−1/2, −y+3/2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4B···O4i | 0.98 | 2.58 | 3.415 (3) | 144 |
| C8—H8···O4ii | 0.95 | 2.51 | 3.229 (2) | 133 |
| C10—H10B···O2iii | 0.99 | 2.56 | 3.312 (2) | 133 |
| C10—H10A···O1iv | 0.99 | 2.58 | 3.461 (2) | 148 |
| C14—H14···O1iv | 0.95 | 2.29 | 3.166 (2) | 153 |
| Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x, y+1, z; (iii) −x, −y+1, −z; (iv) x−1/2, −y+3/2, z+1/2. |
We thank Southwest University (SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (2007BB5369) for financial support.
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Nitroimidazole and its derivatives possess several biological activities such as radiosensitizer, anti-tuberculosis and antimicrobial (Demirayak et al., 1999; Huang et al., 2007; Olender et al., 2009). In view of the therapeutic potentials of nitroimidazole derivatives, we are interested in the research and development of nitroimidazole compounds as drugs. Herein we report the crystal structure of the title compound (I).
The stucture of the title compound (I) is shown in Fig 1. In the molecule the dihedral angle between the benzene and imidazole rings is 3.69 (2)°. The crystal structure is stabilized by weak intermolecular C—H···O hydrogen bonds and significant π–π stacking interactions with a centroid to centroid ditance of 3.614 (1)Å between benzene and imidazole rings related by the symmetry operator (1/2-x, 1/2+y, 1/2-z).