Acta Cryst. (2009). E65, o116 [ doi:10.1107/S1600536808041676 ]
In the title compound, C8H12N4O4, the essentially planar methylcarbamoyloxymethyl group [maximum deviation 0.038 (3) Å] and the imidazole ring make a dihedral angle of 48.47 (3)°. The crystal packing is stabilized by intermolecular N-H
N and C-HO hydrogen bonds, which link the molecules into infinite ribbons running along the a axis, and by weak ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking interactions [centroid-centroid distance = 3.894 (2) Å].
The title compound was prepared by reaction of 1.71 g (0.01 mol) 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol with 0.68 g (0.12 mol) methyl isocyanate catalyzed by 1 g triethylamine in 20 ml toluene at room temperature, yield 86.4%. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a metanol solution at room temperature for two weeks.
All H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å, N—H = 0.86 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2 (1.5 for methyl) times Ueq(C, N).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./hg2452fig1thm.gif)
| Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 40% probability level. |
| C8H12N4O4 | F(000) = 480 |
| Mr = 228.22 | Dx = 1.403 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 2505 reflections |
| a = 9.6959 (12) Å | θ = 2.7–27.1° |
| b = 7.2898 (9) Å | µ = 0.11 mm−1 |
| c = 15.589 (2) Å | T = 273 K |
| β = 101.400 (2)° | Block, yellow |
| V = 1080.1 (2) Å3 | 0.15 × 0.12 × 0.10 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 1622 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.015 |
| graphite | θmax = 25.0°, θmin = 2.3° |
| φ and ω scans | h = −11→11 |
| 5515 measured reflections | k = −8→8 |
| 1921 independent reflections | l = −9→18 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
| wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0404P)2 + 0.2462P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 1921 reflections | Δρmax = 0.19 e Å−3 |
| 146 parameters | Δρmin = −0.14 e Å−3 |
| 0 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (2) |
| C8H12N4O4 | V = 1080.1 (2) Å3 |
| Mr = 228.22 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 9.6959 (12) Å | µ = 0.11 mm−1 |
| b = 7.2898 (9) Å | T = 273 K |
| c = 15.589 (2) Å | 0.15 × 0.12 × 0.10 mm |
| β = 101.400 (2)° |
| Bruker SMART CCD area-detector diffractometer | 1622 reflections with I > 2σ(I) |
| 5515 measured reflections | Rint = 0.015 |
| 1921 independent reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
| wR(F2) = 0.089 | Δρmax = 0.19 e Å−3 |
| S = 1.05 | Δρmin = −0.14 e Å−3 |
| 1921 reflections | Absolute structure: ? |
| 146 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 | 0.41899 (13) | 0.31179 (19) | 0.60227 (7) | 0.0673 (4) | |
| O2 | 0.62309 (12) | 0.35345 (19) | 0.56977 (8) | 0.0693 (4) | |
| O3 | 0.06913 (10) | 0.38773 (15) | 0.39251 (7) | 0.0495 (3) | |
| O4 | −0.13394 (10) | 0.24805 (16) | 0.40569 (7) | 0.0516 (3) | |
| N1 | 0.45446 (13) | 0.11166 (19) | 0.33518 (8) | 0.0511 (3) | |
| N2 | 0.32310 (11) | 0.14897 (15) | 0.43564 (7) | 0.0368 (3) | |
| N3 | 0.50075 (13) | 0.29867 (17) | 0.55195 (8) | 0.0461 (3) | |
| N4 | −0.11627 (13) | 0.41147 (18) | 0.28483 (8) | 0.0489 (3) | |
| H4 | −0.0602 | 0.4739 | 0.2598 | 0.059* | |
| C1 | 0.45604 (14) | 0.21818 (18) | 0.46825 (9) | 0.0374 (3) | |
| C2 | 0.53355 (15) | 0.1938 (2) | 0.40604 (10) | 0.0456 (4) | |
| H2 | 0.6272 | 0.2283 | 0.4111 | 0.055* | |
| C3 | 0.32821 (15) | 0.0863 (2) | 0.35445 (9) | 0.0437 (4) | |
| C4 | 0.20850 (19) | −0.0011 (3) | 0.29424 (12) | 0.0657 (5) | |
| H4A | 0.2356 | −0.0287 | 0.2397 | 0.099* | |
| H4B | 0.1297 | 0.0812 | 0.2841 | 0.099* | |
| H4C | 0.1828 | −0.1125 | 0.3200 | 0.099* | |
| C5 | 0.20058 (15) | 0.1428 (2) | 0.47777 (10) | 0.0453 (4) | |
| H5A | 0.2301 | 0.0991 | 0.5373 | 0.054* | |
| H5B | 0.1326 | 0.0562 | 0.4467 | 0.054* | |
| C6 | 0.13134 (15) | 0.3268 (2) | 0.47920 (10) | 0.0489 (4) | |
| H6A | 0.0591 | 0.3191 | 0.5141 | 0.059* | |
| H6B | 0.2007 | 0.4159 | 0.5064 | 0.059* | |
| C7 | −0.06789 (14) | 0.34081 (19) | 0.36319 (9) | 0.0390 (3) | |
| C8 | −0.26021 (17) | 0.3868 (2) | 0.24023 (11) | 0.0564 (4) | |
| H8A | −0.2734 | 0.2632 | 0.2190 | 0.085* | |
| H8B | −0.2811 | 0.4705 | 0.1918 | 0.085* | |
| H8C | −0.3219 | 0.4104 | 0.2801 | 0.085* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0660 (8) | 0.0934 (10) | 0.0442 (6) | −0.0052 (7) | 0.0153 (6) | −0.0090 (6) |
| O2 | 0.0506 (7) | 0.0844 (9) | 0.0671 (8) | −0.0186 (6) | −0.0026 (6) | −0.0062 (7) |
| O3 | 0.0351 (5) | 0.0590 (7) | 0.0568 (7) | −0.0004 (5) | 0.0146 (5) | 0.0064 (5) |
| O4 | 0.0431 (6) | 0.0645 (7) | 0.0486 (6) | −0.0100 (5) | 0.0123 (5) | 0.0118 (5) |
| N1 | 0.0494 (7) | 0.0567 (8) | 0.0504 (8) | 0.0087 (6) | 0.0176 (6) | −0.0046 (6) |
| N2 | 0.0346 (6) | 0.0373 (6) | 0.0394 (6) | 0.0021 (5) | 0.0091 (5) | 0.0027 (5) |
| N3 | 0.0447 (7) | 0.0477 (7) | 0.0436 (7) | −0.0008 (6) | 0.0029 (6) | 0.0050 (6) |
| N4 | 0.0441 (7) | 0.0564 (8) | 0.0491 (7) | −0.0010 (6) | 0.0162 (6) | 0.0130 (6) |
| C1 | 0.0350 (7) | 0.0356 (7) | 0.0410 (7) | 0.0018 (6) | 0.0062 (6) | 0.0040 (6) |
| C2 | 0.0364 (8) | 0.0477 (8) | 0.0547 (9) | 0.0043 (6) | 0.0141 (7) | 0.0042 (7) |
| C3 | 0.0459 (8) | 0.0405 (8) | 0.0439 (8) | 0.0073 (6) | 0.0071 (6) | −0.0020 (6) |
| C4 | 0.0633 (11) | 0.0710 (12) | 0.0582 (10) | −0.0002 (9) | 0.0007 (8) | −0.0172 (9) |
| C5 | 0.0378 (7) | 0.0522 (9) | 0.0481 (8) | −0.0052 (6) | 0.0138 (6) | 0.0045 (7) |
| C6 | 0.0361 (8) | 0.0641 (10) | 0.0478 (9) | 0.0024 (7) | 0.0112 (6) | −0.0061 (7) |
| C7 | 0.0359 (7) | 0.0385 (7) | 0.0460 (8) | 0.0023 (6) | 0.0162 (6) | −0.0017 (6) |
| C8 | 0.0554 (10) | 0.0609 (10) | 0.0512 (9) | −0.0011 (8) | 0.0062 (7) | 0.0107 (8) |
| O1—N3 | 1.2241 (16) | C1—C2 | 1.3509 (19) |
| O2—N3 | 1.2303 (16) | C2—H2 | 0.9300 |
| O3—C7 | 1.3605 (17) | C3—C4 | 1.485 (2) |
| O3—C6 | 1.4370 (18) | C4—H4A | 0.9600 |
| O4—C7 | 1.2140 (16) | C4—H4B | 0.9600 |
| N1—C3 | 1.3297 (19) | C4—H4C | 0.9600 |
| N1—C2 | 1.354 (2) | C5—C6 | 1.503 (2) |
| N2—C3 | 1.3555 (18) | C5—H5A | 0.9700 |
| N2—C1 | 1.3840 (17) | C5—H5B | 0.9700 |
| N2—C5 | 1.4673 (17) | C6—H6A | 0.9700 |
| N3—C1 | 1.4181 (18) | C6—H6B | 0.9700 |
| N4—C7 | 1.3233 (19) | C8—H8A | 0.9600 |
| N4—C8 | 1.442 (2) | C8—H8B | 0.9600 |
| N4—H4 | 0.8600 | C8—H8C | 0.9600 |
| C7—O3—C6 | 116.02 (11) | H4A—C4—H4C | 109.5 |
| C3—N1—C2 | 105.99 (12) | H4B—C4—H4C | 109.5 |
| C3—N2—C1 | 105.22 (11) | N2—C5—C6 | 112.52 (12) |
| C3—N2—C5 | 126.14 (12) | N2—C5—H5A | 109.1 |
| C1—N2—C5 | 128.64 (11) | C6—C5—H5A | 109.1 |
| O1—N3—O2 | 123.20 (13) | N2—C5—H5B | 109.1 |
| O1—N3—C1 | 120.20 (12) | C6—C5—H5B | 109.1 |
| O2—N3—C1 | 116.60 (13) | H5A—C5—H5B | 107.8 |
| C7—N4—C8 | 121.95 (12) | O3—C6—C5 | 111.56 (12) |
| C7—N4—H4 | 119.0 | O3—C6—H6A | 109.3 |
| C8—N4—H4 | 119.0 | C5—C6—H6A | 109.3 |
| C2—C1—N2 | 107.35 (12) | O3—C6—H6B | 109.3 |
| C2—C1—N3 | 127.06 (13) | C5—C6—H6B | 109.3 |
| N2—C1—N3 | 125.59 (12) | H6A—C6—H6B | 108.0 |
| C1—C2—N1 | 109.76 (13) | O4—C7—N4 | 126.27 (13) |
| C1—C2—H2 | 125.1 | O4—C7—O3 | 122.83 (13) |
| N1—C2—H2 | 125.1 | N4—C7—O3 | 110.89 (12) |
| N1—C3—N2 | 111.67 (13) | N4—C8—H8A | 109.5 |
| N1—C3—C4 | 123.81 (14) | N4—C8—H8B | 109.5 |
| N2—C3—C4 | 124.52 (14) | H8A—C8—H8B | 109.5 |
| C3—C4—H4A | 109.5 | N4—C8—H8C | 109.5 |
| C3—C4—H4B | 109.5 | H8A—C8—H8C | 109.5 |
| H4A—C4—H4B | 109.5 | H8B—C8—H8C | 109.5 |
| C3—C4—H4C | 109.5 | ||
| C3—N2—C1—C2 | −0.11 (15) | C1—N2—C3—N1 | 0.19 (16) |
| C5—N2—C1—C2 | −179.97 (13) | C5—N2—C3—N1 | −179.95 (13) |
| C3—N2—C1—N3 | −179.87 (13) | C1—N2—C3—C4 | 179.78 (15) |
| C5—N2—C1—N3 | 0.3 (2) | C5—N2—C3—C4 | −0.4 (2) |
| O1—N3—C1—C2 | −179.83 (15) | C3—N2—C5—C6 | −104.57 (16) |
| O2—N3—C1—C2 | 0.5 (2) | C1—N2—C5—C6 | 75.25 (18) |
| O1—N3—C1—N2 | −0.1 (2) | C7—O3—C6—C5 | 91.29 (14) |
| O2—N3—C1—N2 | −179.77 (13) | N2—C5—C6—O3 | 66.34 (16) |
| N2—C1—C2—N1 | 0.01 (16) | C8—N4—C7—O4 | 1.1 (2) |
| N3—C1—C2—N1 | 179.76 (13) | C8—N4—C7—O3 | −178.06 (13) |
| C3—N1—C2—C1 | 0.11 (17) | C6—O3—C7—O4 | −2.3 (2) |
| C2—N1—C3—N2 | −0.19 (17) | C6—O3—C7—N4 | 176.83 (12) |
| C2—N1—C3—C4 | −179.78 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N4—H4···N1i | 0.86 | 2.20 | 3.0416 (17) | 165 |
| C2—H2···O4ii | 0.93 | 2.34 | 3.2492 (18) | 166 |
| C8—H8B···O4iii | 0.96 | 2.57 | 3.498 (2) | 164 |
| Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x−1/2, y+1/2, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N4—H4···N1i | 0.86 | 2.20 | 3.0416 (17) | 165 |
| C2—H2···O4ii | 0.93 | 2.34 | 3.2492 (18) | 166 |
| C8—H8B···O4iii | 0.96 | 2.57 | 3.498 (2) | 164 |
| Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x−1/2, y+1/2, −z+1/2. |
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.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin
Cina, S. J., Russell, R. A. & Conradi, S. E. (1996). Am. J. Foren. Med. Path. 17, 343–346.
Karamanakos, P. N., Pappas, P., Boumba, V. A., Thomas, C., Malamas, M., Vougiouklakis, T. & Marselos, M. (2007). Int. J. Toxicol. 26, 423–432.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol is an anti-anaerobic bacteria and anti-infusorium agent to treatment of infection which is called metronidazole (Cina et al., 1996; Karamanakos et al., 2007). The title compound is a derivative of it. In this paper, we report the crystal structure of the title compound.
In (I) (Fig. 1), all bond lengths are normal (Allen et al., 1987). Atoms C4, C5, N3, O1, O2 lie in the plane of the imidazole ring (C1/C2/C3/N1/N2) with maximum deviations 0.004 (2)Å for O1. The essentially planar methyl methylcarbamate moiety (C6—C8/N4/O3/O4) and the imidazole ring make a dihedral angle of 48.47 (3)°. The relatively short distance of 3.894 (2)Å between the centroids of imidazole ring C1/C2/C3/N1/N2 [at (1-X,-Y,1-Z)] indicates the presence of weak π-π interactions, which contribute to the stability of the crystal packing. The crystal packing is also stabilized by intermolecular N—H···N and C—H···O hydrogen bonds,