2-[1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yloxycarbonyl]benzoic acid

Xiao Tao; Lin Yuan; Xiao-Qing Zhang; Jin-Tang Wang

doi:10.1107/S1600536808001268

. 2008 Jan 18;64(Pt 2):o472. doi: 10.1107/S1600536808001268

2-[1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yloxycarbonyl]benzoic acid

Xiao Tao ^a, Lin Yuan ^a, Xiao-Qing Zhang ^b, Jin-Tang Wang ^a,^*

PMCID: PMC2960386 PMID: 21201498

Abstract

The asymmetric unit of the title compound, C₁₅H₁₄ClN₃O₆, contains two independent molecules. The imidazole rings are oriented with respect to the benzene rings at dihedral angles of 19.66 (3) and 21.64 (3)°. In the crystal structure, intermolecular O—H⋯N hydrogen bonds link the molecules into infinite chains.

Related literature

For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₄ClN₃O₆
M _r = 367.74
Monoclinic,
a = 15.214 (3) Å
b = 16.271 (3) Å
c = 15.069 (3) Å
β = 113.86 (3)°
V = 3411.5 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 294 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.903, T _max = 0.950
6938 measured reflections
6682 independent reflections
3559 reflections with I > 2σ(I)
R _int = 0.037
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.175
S = 1.02
6682 reflections
451 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001268/hk2413sup1.cif

e-64-0o472-sup1.cif^{(27.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001268/hk2413Isup2.hkl

e-64-0o472-Isup2.hkl^{(327KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N5ⁱ	0.82	1.81	2.623 (3)	172
O7—H7A⋯N2ⁱⁱ	0.82	1.82	2.621 (3)	166

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

As part of our ongoing studies, we synthesized the title compound, (I), and report herein its crystal structure.

The asymmetric unit of the title compound, (I), contains two independent molecules (Fig. 1), in which the bond lengths are within normal ranges (Allen et al., 1987).

Rings A (C1–C6), B (N1/N2/C13–C15), C (C17–C22) and D (N4/N5/C29–C31) are, of course, planar and the dihedral angles between them are A/B = 19.66 (3)° and C/D = 21.64 (3)°.

In the crystal structure, intermolecular O—H···N hydrogen bonds (Table 1) link the molecules into infinite chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title conpound, ornidazole (14.6 g, 66 mmol), phthalic anhydride (11.8 g, 80 mmol), acetone (80 ml) and pyridine (6 ml) were added into a three-necked round-bottom flask (250 ml) fitted with a mechanical stirrer and a reflux condensing tube. The mixture was stirred until the solids were completely dissolved, and heated to reflux for about 7 h, and then the reaction was stopped and the mixture was cooled. After filtration of the mixture under vacuum, the colorless deposition was obtained (yield; 18 g, 74%). Suitable crystals for X-ray analysis were obtained by dissolving the title compound (0.1 g) in dry methanol (5 ml), and then allowing the solution to evaporate slowly at room temperature for about 12 d.