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

Tao, X.; Yuan, L.; Zhang, X.-Q.; Wang, J.-T.

doi:10.1107/S1600536808001268

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o472

doi:10.1107/S1600536808001268

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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 and Jin-Tang Wang ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bNanjing Huawei Medicinal Science Development Co. Ltd, Nanjing 210036, People's Republic of China
^*Correspondence e-mail: wjt@njut.edu.cn

(Received 19 December 2007; accepted 12 January 2008; online 18 January 2008)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.066
wR(F²) = 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

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
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

	Fig. 1. Ellipsoid plot.
	Fig. 2. Packing diagram.

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

Crystal data top

C₁₅H₁₄ClN₃O₆	F(000) = 1520
M_r = 367.74	D_x = 1.432 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 444–447 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.214 (3) Å	Cell parameters from 25 reflections
b = 16.271 (3) Å	θ = 10–13°
c = 15.069 (3) Å	µ = 0.26 mm⁻¹
β = 113.86 (3)°	T = 294 K
V = 3411.5 (14) Å³	Block, colourless
Z = 8	0.40 × 0.30 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	3559 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 26.0°, θ_min = 1.5°
ω/2θ scans	h = −18→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
T_min = 0.903, T_max = 0.950	l = −16→18
6938 measured reflections	3 standard reflections every 120 min
6682 independent reflections	intensity decay: none

Refinement top

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) = 0.175	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.07P)² + 1.25P] where P = (F_o² + 2F_c²)/3
6682 reflections	(Δ/σ)_max < 0.001
451 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₅H₁₄ClN₃O₆	V = 3411.5 (14) Å³
M_r = 367.74	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.214 (3) Å	µ = 0.26 mm⁻¹
b = 16.271 (3) Å	T = 294 K
c = 15.069 (3) Å	0.40 × 0.30 × 0.20 mm
β = 113.86 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3559 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.037
T_min = 0.903, T_max = 0.950	3 standard reflections every 120 min
6938 measured reflections	intensity decay: none
6682 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.02	Δρ_max = 0.41 e Å⁻³
6682 reflections	Δρ_min = −0.36 e Å⁻³
451 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Cl1	0.11705 (11)	0.43257 (8)	0.72492 (11)	0.1116 (6)
Cl2	−0.38901 (14)	0.04807 (9)	0.66545 (14)	0.1333 (7)
O1	0.3761 (2)	0.03250 (17)	1.0499 (2)	0.0784 (9)
H1B	0.3710	0.0047	1.0026	0.118*
O2	0.3562 (2)	0.13615 (16)	0.94718 (18)	0.0613 (7)
O3	0.3744 (2)	0.32764 (19)	0.96664 (19)	0.0684 (8)
O4	0.23091 (17)	0.27469 (14)	0.94386 (16)	0.0485 (6)
O5	0.1328 (2)	0.2233 (2)	0.6314 (2)	0.0748 (8)
O6	0.1459 (2)	0.0990 (2)	0.5886 (2)	0.0887 (10)
O7	−0.1465 (2)	0.39839 (15)	0.55531 (19)	0.0719 (9)
H7A	−0.1519	0.4404	0.5828	0.108*
O8	−0.1401 (2)	0.33919 (14)	0.69075 (19)	0.0596 (7)
O9	−0.11021 (18)	0.16192 (17)	0.77884 (18)	0.0592 (7)
O10	−0.25765 (16)	0.19193 (14)	0.66714 (15)	0.0453 (6)
O11	−0.3413 (3)	0.4576 (2)	0.8743 (2)	0.1134 (14)
O12	−0.3404 (2)	0.3246 (2)	0.8740 (2)	0.0832 (10)
N1	0.11477 (19)	0.16366 (16)	0.7989 (2)	0.0426 (7)
N2	0.1320 (2)	0.03336 (18)	0.8448 (2)	0.0554 (8)
N3	0.1364 (2)	0.1490 (2)	0.6445 (2)	0.0592 (9)
N4	−0.37734 (19)	0.32555 (17)	0.6748 (2)	0.0438 (7)
N5	−0.3757 (2)	0.4369 (2)	0.5904 (2)	0.0597 (9)
N6	−0.3466 (3)	0.3912 (3)	0.8340 (2)	0.0684 (10)
C1	0.3666 (3)	0.3017 (3)	1.1689 (3)	0.0580 (11)
H1A	0.3550	0.3577	1.1582	0.070*
C2	0.3935 (3)	0.2701 (3)	1.2607 (3)	0.0673 (13)
H2B	0.3988	0.3047	1.3117	0.081*
C3	0.4129 (3)	0.1871 (3)	1.2777 (3)	0.0676 (12)
H3A	0.4320	0.1663	1.3402	0.081*
C4	0.4037 (3)	0.1351 (3)	1.2018 (3)	0.0580 (11)
H4A	0.4166	0.0793	1.2133	0.070*
C5	0.3755 (2)	0.1661 (2)	1.1088 (2)	0.0464 (9)
C6	0.3568 (2)	0.2497 (2)	1.0920 (2)	0.0462 (9)
C7	0.3675 (3)	0.1105 (2)	1.0262 (3)	0.0498 (9)
C8	0.3245 (3)	0.2879 (2)	0.9941 (3)	0.0475 (9)
C9	0.1664 (3)	0.3935 (2)	0.8436 (3)	0.0749 (13)
H9A	0.2255	0.4225	0.8812	0.090*
H9B	0.1219	0.4027	0.8740	0.090*
C10	0.1872 (3)	0.3018 (2)	0.8441 (2)	0.0476 (9)
H10A	0.2298	0.2909	0.8110	0.057*
C11	0.0955 (2)	0.2518 (2)	0.7990 (3)	0.0491 (9)
H11A	0.0560	0.2615	0.8349	0.059*
H11B	0.0596	0.2701	0.7328	0.059*
C12	0.1003 (3)	0.1285 (3)	0.9559 (3)	0.0616 (11)
H12A	0.1046	0.0788	0.9918	0.092*
H12B	0.0378	0.1523	0.9380	0.092*
H12C	0.1484	0.1666	0.9954	0.092*
C13	0.1158 (2)	0.1095 (2)	0.8677 (3)	0.0465 (9)
C14	0.1408 (3)	0.0381 (2)	0.7593 (3)	0.0569 (10)
H14A	0.1517	−0.0061	0.7259	0.068*
C15	0.1311 (3)	0.1176 (2)	0.7298 (3)	0.0477 (9)
C17	−0.1188 (3)	0.1073 (2)	0.5763 (3)	0.0552 (10)
H17A	−0.1214	0.0583	0.6069	0.066*
C18	−0.0988 (3)	0.1060 (3)	0.4947 (3)	0.0643 (11)
H18A	−0.0887	0.0560	0.4703	0.077*
C19	−0.0939 (3)	0.1783 (3)	0.4494 (3)	0.0594 (11)
H19A	−0.0811	0.1773	0.3940	0.071*
C20	−0.1079 (2)	0.2521 (2)	0.4867 (2)	0.0477 (9)
H20A	−0.1032	0.3009	0.4568	0.057*
C21	−0.1288 (2)	0.2548 (2)	0.5676 (2)	0.0389 (8)
C22	−0.1352 (2)	0.1814 (2)	0.6130 (2)	0.0399 (8)
C23	−0.1395 (3)	0.3347 (2)	0.6110 (3)	0.0459 (9)
C24	−0.1631 (3)	0.1788 (2)	0.6968 (3)	0.0428 (8)
C25	−0.3119 (3)	0.1052 (3)	0.7666 (3)	0.0737 (13)
H25A	−0.3391	0.1072	0.8147	0.088*
H25B	−0.2503	0.0777	0.7955	0.088*
C26	−0.2968 (3)	0.1925 (2)	0.7394 (3)	0.0491 (9)
H26A	−0.2528	0.2216	0.7972	0.059*
C27	−0.3904 (2)	0.2392 (2)	0.6947 (3)	0.0490 (9)
H27A	−0.4314	0.2125	0.6345	0.059*
H27B	−0.4229	0.2368	0.7384	0.059*
C28	−0.4060 (3)	0.3050 (3)	0.5004 (3)	0.0655 (11)
H28A	−0.4093	0.3398	0.4476	0.098*
H28B	−0.4660	0.2767	0.4832	0.098*
H28C	−0.3553	0.2656	0.5136	0.098*
C29	−0.3866 (3)	0.3556 (2)	0.5877 (3)	0.0494 (9)
C30	−0.3610 (3)	0.4604 (3)	0.6814 (3)	0.0618 (11)
H30A	−0.3517	0.5142	0.7039	0.074*
C31	−0.3617 (3)	0.3934 (2)	0.7348 (3)	0.0508 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1335 (12)	0.0557 (8)	0.1106 (11)	0.0032 (8)	0.0131 (9)	0.0320 (7)
Cl2	0.1632 (15)	0.0625 (9)	0.1512 (15)	−0.0410 (9)	0.0400 (12)	0.0081 (9)
O1	0.128 (3)	0.0514 (19)	0.0574 (18)	−0.0074 (17)	0.0396 (18)	−0.0063 (14)
O2	0.085 (2)	0.0620 (18)	0.0400 (15)	0.0030 (15)	0.0285 (14)	−0.0037 (13)
O3	0.0697 (19)	0.086 (2)	0.0548 (17)	−0.0269 (16)	0.0310 (15)	−0.0091 (15)
O4	0.0524 (16)	0.0461 (14)	0.0426 (14)	−0.0039 (12)	0.0146 (12)	−0.0052 (11)
O5	0.099 (2)	0.060 (2)	0.0677 (19)	−0.0005 (17)	0.0358 (17)	0.0091 (16)
O6	0.124 (3)	0.083 (2)	0.078 (2)	−0.011 (2)	0.059 (2)	−0.0271 (19)
O7	0.126 (3)	0.0319 (15)	0.0609 (17)	0.0040 (15)	0.0406 (17)	0.0059 (13)
O8	0.093 (2)	0.0387 (15)	0.0592 (17)	−0.0026 (13)	0.0427 (16)	−0.0068 (13)
O9	0.0560 (16)	0.0704 (19)	0.0476 (16)	0.0104 (14)	0.0173 (13)	0.0095 (14)
O10	0.0485 (15)	0.0482 (14)	0.0430 (13)	0.0016 (12)	0.0225 (12)	0.0073 (11)
O11	0.165 (4)	0.093 (3)	0.071 (2)	0.024 (3)	0.037 (2)	−0.026 (2)
O12	0.098 (2)	0.098 (3)	0.0586 (19)	0.004 (2)	0.0372 (18)	0.0143 (18)
N1	0.0440 (17)	0.0327 (16)	0.0447 (17)	0.0032 (13)	0.0115 (13)	−0.0036 (14)
N2	0.066 (2)	0.0311 (17)	0.066 (2)	−0.0015 (15)	0.0234 (17)	−0.0005 (15)
N3	0.061 (2)	0.056 (2)	0.056 (2)	−0.0040 (18)	0.0196 (17)	−0.0071 (19)
N4	0.0451 (17)	0.0426 (18)	0.0454 (17)	0.0005 (14)	0.0199 (14)	0.0039 (14)
N5	0.067 (2)	0.050 (2)	0.061 (2)	0.0025 (17)	0.0253 (18)	0.0116 (17)
N6	0.071 (2)	0.082 (3)	0.049 (2)	0.007 (2)	0.0225 (18)	−0.006 (2)
C1	0.053 (2)	0.070 (3)	0.049 (2)	0.003 (2)	0.0197 (19)	−0.023 (2)
C2	0.056 (3)	0.103 (4)	0.042 (2)	−0.002 (3)	0.0194 (19)	−0.029 (2)
C3	0.058 (3)	0.109 (4)	0.037 (2)	−0.006 (3)	0.0205 (19)	−0.007 (2)
C4	0.062 (3)	0.073 (3)	0.042 (2)	−0.013 (2)	0.0236 (19)	−0.003 (2)
C5	0.043 (2)	0.060 (3)	0.038 (2)	−0.0115 (18)	0.0194 (16)	−0.0109 (18)
C6	0.042 (2)	0.057 (2)	0.040 (2)	−0.0054 (18)	0.0172 (16)	−0.0101 (18)
C7	0.057 (2)	0.052 (2)	0.043 (2)	−0.0065 (19)	0.0218 (18)	−0.0092 (19)
C8	0.051 (2)	0.047 (2)	0.047 (2)	−0.0061 (18)	0.0213 (19)	−0.0142 (18)
C9	0.098 (3)	0.039 (2)	0.080 (3)	0.005 (2)	0.027 (3)	−0.001 (2)
C10	0.061 (2)	0.0322 (19)	0.047 (2)	0.0016 (17)	0.0196 (19)	−0.0002 (16)
C11	0.047 (2)	0.034 (2)	0.058 (2)	0.0078 (16)	0.0130 (18)	−0.0016 (17)
C12	0.068 (3)	0.061 (3)	0.059 (3)	0.001 (2)	0.029 (2)	0.001 (2)
C13	0.046 (2)	0.040 (2)	0.052 (2)	−0.0008 (17)	0.0182 (18)	−0.0039 (18)
C14	0.066 (3)	0.040 (2)	0.063 (3)	−0.0031 (19)	0.025 (2)	−0.0110 (19)
C15	0.053 (2)	0.036 (2)	0.052 (2)	−0.0026 (17)	0.0184 (18)	−0.0069 (18)
C17	0.071 (3)	0.035 (2)	0.063 (3)	0.0029 (19)	0.031 (2)	−0.0004 (18)
C18	0.077 (3)	0.047 (2)	0.072 (3)	0.003 (2)	0.033 (2)	−0.019 (2)
C19	0.064 (3)	0.069 (3)	0.055 (2)	−0.001 (2)	0.033 (2)	−0.010 (2)
C20	0.054 (2)	0.048 (2)	0.045 (2)	−0.0027 (18)	0.0246 (18)	0.0026 (17)
C21	0.0421 (19)	0.0359 (19)	0.0389 (19)	0.0000 (16)	0.0165 (16)	0.0000 (15)
C22	0.041 (2)	0.0353 (19)	0.044 (2)	−0.0007 (16)	0.0175 (16)	−0.0013 (15)
C23	0.052 (2)	0.034 (2)	0.051 (2)	−0.0003 (16)	0.0193 (18)	−0.0002 (17)
C24	0.048 (2)	0.0344 (19)	0.047 (2)	−0.0010 (17)	0.0209 (18)	0.0019 (16)
C25	0.091 (3)	0.064 (3)	0.079 (3)	0.007 (3)	0.048 (3)	0.028 (2)
C26	0.056 (2)	0.050 (2)	0.050 (2)	−0.0022 (18)	0.0307 (19)	0.0088 (18)
C27	0.049 (2)	0.047 (2)	0.057 (2)	−0.0090 (18)	0.0280 (19)	0.0007 (18)
C28	0.074 (3)	0.073 (3)	0.047 (2)	0.008 (2)	0.022 (2)	−0.002 (2)
C29	0.046 (2)	0.059 (3)	0.042 (2)	0.0018 (19)	0.0163 (17)	0.0036 (18)
C30	0.070 (3)	0.045 (2)	0.071 (3)	0.001 (2)	0.028 (2)	0.000 (2)
C31	0.054 (2)	0.055 (2)	0.044 (2)	0.0006 (19)	0.0203 (18)	−0.0033 (19)

Geometric parameters (Å, º) top

Cl1—C9	1.755 (4)	C9—C10	1.524 (5)
Cl2—C25	1.765 (5)	C9—H9A	0.9700
O1—C7	1.311 (4)	C9—H9B	0.9700
O1—H1B	0.8200	C10—C11	1.517 (5)
O2—C7	1.207 (4)	C10—H10A	0.9800
O3—C8	1.191 (4)	C11—H11A	0.9700
O4—C8	1.333 (4)	C11—H11B	0.9700
O4—C10	1.446 (4)	C12—C13	1.474 (5)
O5—N3	1.222 (4)	C12—H12A	0.9600
O6—N3	1.221 (4)	C12—H12B	0.9600
O7—C23	1.310 (4)	C12—H12C	0.9600
O7—H7A	0.8200	C14—C15	1.357 (5)
O8—C23	1.207 (4)	C14—H14A	0.9300
O9—C24	1.203 (4)	C15—N3	1.416 (5)
O10—C24	1.340 (4)	C17—C18	1.381 (5)
O10—C26	1.436 (4)	C17—C22	1.390 (5)
O11—N6	1.226 (5)	C17—H17A	0.9300
O12—N6	1.225 (4)	C18—C19	1.378 (6)
N1—C13	1.356 (4)	C18—H18A	0.9300
N1—C15	1.383 (4)	C19—C20	1.379 (5)
N1—C11	1.465 (4)	C19—H19A	0.9300
N2—C13	1.336 (4)	C20—C21	1.379 (5)
N2—C14	1.351 (5)	C20—H20A	0.9300
N4—C29	1.353 (4)	C21—C22	1.398 (4)
N4—C31	1.385 (4)	C21—C23	1.494 (5)
N4—C27	1.468 (4)	C22—C24	1.486 (5)
N5—C29	1.331 (5)	C25—C26	1.522 (5)
N5—C30	1.351 (5)	C25—H25A	0.9700
C1—C2	1.373 (6)	C25—H25B	0.9700
C1—C6	1.394 (5)	C26—C27	1.511 (5)
C1—H1A	0.9300	C26—H26A	0.9800
C2—C3	1.384 (6)	C27—H27A	0.9700
C2—H2B	0.9300	C27—H27B	0.9700
C3—C4	1.384 (5)	C28—C29	1.478 (5)
C3—H3A	0.9300	C28—H28A	0.9600
C4—C5	1.383 (5)	C28—H28B	0.9600
C4—H4A	0.9300	C28—H28C	0.9600
C5—C6	1.392 (5)	C30—C31	1.357 (5)
C5—C7	1.503 (5)	C30—H30A	0.9300
C6—C8	1.489 (5)	C31—N6	1.419 (5)

C7—O1—H1B	109.5	N2—C13—N1	110.6 (3)
C8—O4—C10	118.6 (3)	N2—C13—C12	122.7 (3)
C23—O7—H7A	109.5	N1—C13—C12	126.7 (3)
C24—O10—C26	117.8 (3)	N2—C14—C15	109.1 (3)
C13—N1—C15	105.9 (3)	N2—C14—H14A	125.5
C13—N1—C11	125.1 (3)	C15—C14—H14A	125.5
C15—N1—C11	128.9 (3)	C14—C15—N1	107.4 (3)
C13—N2—C14	107.0 (3)	C14—C15—N3	127.0 (3)
O6—N3—O5	123.8 (4)	N1—C15—N3	125.6 (3)
O6—N3—C15	116.9 (3)	C18—C17—C22	120.5 (4)
O5—N3—C15	119.2 (3)	C18—C17—H17A	119.8
C29—N4—C31	105.5 (3)	C22—C17—H17A	119.8
C29—N4—C27	125.1 (3)	C19—C18—C17	120.3 (4)
C31—N4—C27	129.1 (3)	C19—C18—H18A	119.9
C29—N5—C30	106.3 (3)	C17—C18—H18A	119.9
O12—N6—O11	124.0 (4)	C18—C19—C20	119.5 (3)
O12—N6—C31	119.2 (4)	C18—C19—H19A	120.2
O11—N6—C31	116.8 (4)	C20—C19—H19A	120.2
C2—C1—C6	119.9 (4)	C19—C20—C21	121.1 (3)
C2—C1—H1A	120.1	C19—C20—H20A	119.4
C6—C1—H1A	120.1	C21—C20—H20A	119.4
C1—C2—C3	120.4 (4)	C20—C21—C22	119.5 (3)
C1—C2—H2B	119.8	C20—C21—C23	121.3 (3)
C3—C2—H2B	119.8	C22—C21—C23	119.2 (3)
C4—C3—C2	120.0 (4)	C17—C22—C21	119.1 (3)
C4—C3—H3A	120.0	C17—C22—C24	118.1 (3)
C2—C3—H3A	120.0	C21—C22—C24	122.7 (3)
C5—C4—C3	120.0 (4)	O8—C23—O7	123.9 (3)
C5—C4—H4A	120.0	O8—C23—C21	122.3 (3)
C3—C4—H4A	120.0	O7—C23—C21	113.8 (3)
C4—C5—C6	119.8 (3)	O9—C24—O10	124.1 (3)
C4—C5—C7	120.5 (4)	O9—C24—C22	125.3 (3)
C6—C5—C7	119.7 (3)	O10—C24—C22	110.4 (3)
C5—C6—C1	119.8 (3)	C26—C25—Cl2	112.3 (3)
C5—C6—C8	123.3 (3)	C26—C25—H25A	109.1
C1—C6—C8	116.9 (4)	Cl2—C25—H25A	109.1
O2—C7—O1	124.2 (3)	C26—C25—H25B	109.1
O2—C7—C5	122.8 (4)	Cl2—C25—H25B	109.1
O1—C7—C5	113.0 (3)	H25A—C25—H25B	107.9
O3—C8—O4	125.1 (4)	O10—C26—C27	105.7 (3)
O3—C8—C6	124.7 (3)	O10—C26—C25	110.6 (3)
O4—C8—C6	110.1 (3)	C27—C26—C25	111.7 (3)
C10—C9—Cl1	111.2 (3)	O10—C26—H26A	109.6
C10—C9—H9A	109.4	C27—C26—H26A	109.6
Cl1—C9—H9A	109.4	C25—C26—H26A	109.6
C10—C9—H9B	109.4	N4—C27—C26	113.0 (3)
Cl1—C9—H9B	109.4	N4—C27—H27A	109.0
H9A—C9—H9B	108.0	C26—C27—H27A	109.0
O4—C10—C11	104.8 (3)	N4—C27—H27B	109.0
O4—C10—C9	108.1 (3)	C26—C27—H27B	109.0
C11—C10—C9	111.8 (3)	H27A—C27—H27B	107.8
O4—C10—H10A	110.7	C29—C28—H28A	109.5
C11—C10—H10A	110.7	C29—C28—H28B	109.5
C9—C10—H10A	110.7	H28A—C28—H28B	109.5
N1—C11—C10	112.1 (3)	C29—C28—H28C	109.5
N1—C11—H11A	109.2	H28A—C28—H28C	109.5
C10—C11—H11A	109.2	H28B—C28—H28C	109.5
N1—C11—H11B	109.2	N5—C29—N4	111.5 (3)
C10—C11—H11B	109.2	N5—C29—C28	124.0 (4)
H11A—C11—H11B	107.9	N4—C29—C28	124.5 (4)
C13—C12—H12A	109.5	N5—C30—C31	109.7 (4)
C13—C12—H12B	109.5	N5—C30—H30A	125.2
H12A—C12—H12B	109.5	C31—C30—H30A	125.2
C13—C12—H12C	109.5	C30—C31—N4	107.1 (3)
H12A—C12—H12C	109.5	C30—C31—N6	127.4 (4)
H12B—C12—H12C	109.5	N4—C31—N6	125.5 (4)

C10—O4—C8—O3	7.7 (5)	C6—C5—C7—O2	8.8 (5)
C10—O4—C8—C6	−175.5 (3)	C4—C5—C7—O1	9.1 (5)
C8—O4—C10—C11	159.8 (3)	C6—C5—C7—O1	−172.6 (3)
C8—O4—C10—C9	−80.9 (4)	C5—C6—C8—O3	−104.2 (5)
C26—O10—C24—O9	5.3 (5)	C1—C6—C8—O3	76.8 (5)
C26—O10—C24—C22	−179.2 (3)	C5—C6—C8—O4	78.9 (4)
C24—O10—C26—C27	158.9 (3)	C1—C6—C8—O4	−100.0 (4)
C24—O10—C26—C25	−80.0 (4)	Cl1—C9—C10—O4	177.8 (3)
C13—N1—C11—C10	94.9 (4)	Cl1—C9—C10—C11	−67.4 (4)
C15—N1—C11—C10	−88.2 (4)	O4—C10—C11—N1	−63.4 (4)
C15—N1—C13—N2	0.1 (4)	C9—C10—C11—N1	179.8 (3)
C11—N1—C13—N2	177.6 (3)	N2—C14—C15—N1	−0.6 (4)
C15—N1—C13—C12	−179.0 (3)	N2—C14—C15—N3	179.4 (3)
C11—N1—C13—C12	−1.5 (6)	C14—C15—N3—O6	4.0 (6)
C13—N1—C15—C14	0.3 (4)	N1—C15—N3—O6	−176.0 (3)
C11—N1—C15—C14	−177.1 (3)	C14—C15—N3—O5	−174.9 (4)
C13—N1—C15—N3	−179.7 (3)	N1—C15—N3—O5	5.1 (6)
C11—N1—C15—N3	3.0 (6)	C22—C17—C18—C19	0.7 (6)
C14—N2—C13—N1	−0.5 (4)	C18—C17—C22—C21	−1.6 (5)
C14—N2—C13—C12	178.7 (3)	C18—C17—C22—C24	175.8 (3)
C13—N2—C14—C15	0.7 (4)	C17—C18—C19—C20	0.8 (6)
C29—N4—C27—C26	97.5 (4)	C18—C19—C20—C21	−1.3 (6)
C31—N4—C27—C26	−88.5 (4)	C19—C20—C21—C22	0.4 (5)
C31—N4—C29—N5	1.3 (4)	C19—C20—C21—C23	177.1 (3)
C27—N4—C29—N5	176.5 (3)	C20—C21—C22—C17	1.0 (5)
C31—N4—C29—C28	−178.8 (3)	C23—C21—C22—C17	−175.7 (3)
C27—N4—C29—C28	−3.6 (5)	C20—C21—C22—C24	−176.3 (3)
C29—N4—C31—C30	−0.9 (4)	C23—C21—C22—C24	7.0 (5)
C27—N4—C31—C30	−175.8 (3)	C20—C21—C23—O8	−166.0 (3)
C29—N4—C31—N6	−179.1 (3)	C22—C21—C23—O8	10.7 (5)
C27—N4—C31—N6	5.9 (6)	C20—C21—C23—O7	12.9 (5)
C30—N5—C29—N4	−1.3 (4)	C22—C21—C23—O7	−170.4 (3)
C30—N5—C29—C28	178.9 (4)	C17—C22—C24—O9	72.7 (5)
C29—N5—C30—C31	0.7 (4)	C21—C22—C24—O9	−110.0 (4)
C6—C1—C2—C3	1.3 (6)	C17—C22—C24—O10	−102.8 (4)
C2—C1—C6—C5	−0.8 (5)	C21—C22—C24—O10	74.6 (4)
C2—C1—C6—C8	178.2 (3)	Cl2—C25—C26—O10	−58.1 (4)
C1—C2—C3—C4	−1.0 (6)	Cl2—C25—C26—C27	59.4 (4)
C2—C3—C4—C5	0.2 (6)	O10—C26—C27—N4	−64.1 (4)
C3—C4—C5—C6	0.3 (5)	C25—C26—C27—N4	175.5 (3)
C3—C4—C5—C7	178.6 (3)	N5—C30—C31—N4	0.1 (4)
C4—C5—C6—C1	0.0 (5)	N5—C30—C31—N6	178.3 (3)
C7—C5—C6—C1	−178.3 (3)	C30—C31—N6—O12	−172.9 (4)
C4—C5—C6—C8	−178.9 (3)	N4—C31—N6—O12	5.0 (6)
C7—C5—C6—C8	2.8 (5)	C30—C31—N6—O11	7.5 (6)
C4—C5—C7—O2	−169.5 (4)	N4—C31—N6—O11	−174.5 (4)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClN₃O₆
M_r	367.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	15.214 (3), 16.271 (3), 15.069 (3)
β (°)	113.86 (3)
V (Å³)	3411.5 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.903, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	6938, 6682, 3559
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.175, 1.02
No. of reflections	6682
No. of parameters	451
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.36

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N5ⁱ	0.82	1.81	2.623 (3)	172.00
O7—H7A···N2ⁱⁱ	0.82	1.82	2.621 (3)	166.00

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2.

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. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Version 5. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 2| February 2008| Page o472

doi:10.1107/S1600536808001268

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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