2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-bromo-benzoate.

In the title compound, C(13)H(12)BrN(3)O(4), the dihedral angle between the benzene and imidazole rings is 30.6 (2)°. In the crystal, mol-ecules are linked into chains parallel to [001] by C-H⋯O hydrogen bonds. The crystal packing is further consolidated by π-π inter-actions [centroid-centroid distance = 3.482 (2) Å].

Related literature

For background information and the crystal structure of the 4-flouro analogue of the title compound, see: Yousuf et al. (2012 ▶).

Experimental

Crystal data

C13H12BrN3O4

M = 354.17

Monoclinic,

a = 14.554 (4) Å

b = 8.836 (2) Å

c = 11.563 (3) Å

β = 105.427 (6)°

V = 1433.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.89 mm−1

T = 273 K

0.33 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.449, T max = 0.610

8200 measured reflections

2601 independent reflections

1959 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.04

2601 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012688/pv2520sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012688/pv2520Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012688/pv2520Isup3.cml

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

C13H12BrN3O4	F(000) = 712
Mr = 354.17	Dx = 1.641 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2494 reflections
a = 14.554 (4) Å	θ = 2.7–24.1°
b = 8.836 (2) Å	µ = 2.89 mm−1
c = 11.563 (3) Å	T = 273 K
β = 105.427 (6)°	Block, colorles
V = 1433.3 (7) Å3	0.33 × 0.20 × 0.19 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2601 independent reflections
Radiation source: fine-focus sealed tube	1959 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
Tmin = 0.449, Tmax = 0.610	k = −10→10
8200 measured reflections	l = −14→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.7664P] where P = (Fo2 + 2Fc2)/3
2601 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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
Br1	0.39287 (3)	0.03857 (5)	0.11564 (3)	0.0748 (2)
O1	0.3629 (3)	0.3331 (3)	0.2376 (3)	0.1003 (11)
O2	0.25716 (17)	0.3109 (3)	0.3428 (2)	0.0606 (6)
O3	0.1411 (3)	0.7613 (3)	0.4002 (3)	0.0981 (10)
O4	0.1559 (3)	0.8059 (3)	0.5864 (3)	0.1087 (11)
N1	0.11680 (18)	0.4509 (3)	0.4402 (2)	0.0471 (6)
N2	0.1099 (2)	0.3517 (4)	0.6143 (3)	0.0667 (8)
N3	0.1438 (2)	0.7198 (4)	0.5010 (3)	0.0696 (9)
C1	0.3499 (3)	0.0609 (4)	0.4570 (3)	0.0623 (9)
H1A	0.3271	0.1295	0.5038	0.075*
C2	0.3779 (3)	−0.0807 (5)	0.5015 (4)	0.0747 (11)
H2B	0.3749	−0.1072	0.5783	0.090*
C3	0.4103 (3)	−0.1832 (5)	0.4319 (4)	0.0778 (12)
H3A	0.4292	−0.2792	0.4620	0.093*
C4	0.4151 (3)	−0.1450 (4)	0.3185 (4)	0.0664 (10)
H4A	0.4367	−0.2151	0.2717	0.080*
C5	0.3879 (2)	−0.0030 (4)	0.2746 (3)	0.0498 (8)
C6	0.3552 (2)	0.1034 (4)	0.3431 (3)	0.0475 (7)
C7	0.3277 (3)	0.2592 (4)	0.3011 (3)	0.0541 (8)
C8	0.2178 (3)	0.4561 (4)	0.2996 (3)	0.0618 (9)
H8A	0.2169	0.4689	0.2160	0.074*
H8B	0.2556	0.5368	0.3459	0.074*
C9	0.1188 (3)	0.4590 (4)	0.3138 (3)	0.0575 (9)
H9A	0.0875	0.5514	0.2785	0.069*
H9B	0.0832	0.3743	0.2704	0.069*
C10	0.1311 (2)	0.5647 (3)	0.5247 (3)	0.0511 (8)
C11	0.1268 (3)	0.5010 (4)	0.6297 (3)	0.0631 (9)
H11A	0.1343	0.5528	0.7016	0.076*
C12	0.1047 (2)	0.3241 (4)	0.4998 (3)	0.0555 (8)
C13	0.0869 (3)	0.1719 (4)	0.4440 (4)	0.0826 (12)
H13A	0.0630	0.1058	0.4952	0.124*
H13B	0.1453	0.1316	0.4332	0.124*
H13C	0.0408	0.1798	0.3675	0.124*

	U11	U22	U33	U12	U13	U23
Br1	0.1056 (4)	0.0702 (3)	0.0535 (3)	0.0046 (2)	0.0298 (2)	−0.00709 (18)
O1	0.134 (3)	0.0601 (16)	0.141 (3)	0.0125 (17)	0.096 (2)	0.0205 (18)
O2	0.0806 (16)	0.0593 (14)	0.0483 (13)	0.0208 (12)	0.0282 (12)	0.0138 (11)
O3	0.158 (3)	0.0530 (16)	0.095 (2)	−0.0046 (18)	0.054 (2)	0.0083 (15)
O4	0.169 (3)	0.0605 (17)	0.108 (3)	−0.011 (2)	0.056 (2)	−0.0356 (18)
N1	0.0498 (14)	0.0417 (14)	0.0480 (15)	0.0060 (11)	0.0097 (12)	−0.0016 (12)
N2	0.0730 (19)	0.068 (2)	0.0620 (19)	0.0077 (16)	0.0231 (16)	0.0130 (16)
N3	0.083 (2)	0.0497 (17)	0.081 (2)	0.0018 (15)	0.0311 (19)	−0.0153 (17)
C1	0.067 (2)	0.072 (2)	0.050 (2)	0.0040 (18)	0.0192 (17)	0.0049 (17)
C2	0.075 (3)	0.088 (3)	0.064 (2)	0.010 (2)	0.023 (2)	0.029 (2)
C3	0.074 (3)	0.063 (2)	0.097 (3)	0.010 (2)	0.025 (2)	0.028 (2)
C4	0.069 (2)	0.052 (2)	0.079 (3)	0.0061 (18)	0.020 (2)	0.0020 (19)
C5	0.0503 (18)	0.0488 (17)	0.0488 (19)	−0.0028 (14)	0.0106 (15)	−0.0015 (14)
C6	0.0488 (17)	0.0480 (16)	0.0456 (17)	−0.0023 (14)	0.0123 (14)	−0.0019 (14)
C7	0.070 (2)	0.0479 (17)	0.0491 (19)	−0.0027 (16)	0.0235 (17)	−0.0046 (15)
C8	0.088 (3)	0.054 (2)	0.047 (2)	0.0189 (18)	0.0245 (19)	0.0130 (16)
C9	0.074 (2)	0.0487 (19)	0.0434 (19)	0.0132 (17)	0.0044 (17)	0.0003 (15)
C10	0.0562 (19)	0.0445 (17)	0.054 (2)	0.0075 (14)	0.0159 (16)	−0.0058 (14)
C11	0.071 (2)	0.068 (2)	0.051 (2)	0.0093 (18)	0.0186 (18)	−0.0037 (17)
C12	0.0513 (19)	0.0473 (18)	0.066 (2)	0.0026 (15)	0.0128 (16)	0.0060 (17)
C13	0.095 (3)	0.050 (2)	0.102 (3)	−0.011 (2)	0.024 (3)	−0.002 (2)

Br1—C5	1.895 (3)	C3—C4	1.374 (5)
O1—C7	1.195 (4)	C3—H3A	0.9300
O2—C7	1.326 (4)	C4—C5	1.372 (5)
O2—C8	1.439 (4)	C4—H4A	0.9300
O3—N3	1.213 (4)	C5—C6	1.393 (4)
O4—N3	1.221 (4)	C6—C7	1.479 (5)
N1—C12	1.351 (4)	C8—C9	1.494 (5)
N1—C10	1.379 (4)	C8—H8A	0.9700
N1—C9	1.472 (4)	C8—H8B	0.9700
N2—C12	1.328 (4)	C9—H9A	0.9700
N2—C11	1.345 (5)	C9—H9B	0.9700
N3—C10	1.420 (5)	C10—C11	1.355 (5)
C1—C2	1.372 (5)	C11—H11A	0.9300
C1—C6	1.391 (5)	C12—C13	1.485 (5)
C1—H1A	0.9300	C13—H13A	0.9600
C2—C3	1.376 (6)	C13—H13B	0.9600
C2—H2B	0.9300	C13—H13C	0.9600
C7—O2—C8	117.1 (3)	O2—C7—C6	111.7 (3)
C12—N1—C10	105.0 (3)	O2—C8—C9	106.5 (3)
C12—N1—C9	125.9 (3)	O2—C8—H8A	110.4
C10—N1—C9	129.0 (3)	C9—C8—H8A	110.4
C12—N2—C11	105.8 (3)	O2—C8—H8B	110.4
O3—N3—O4	123.4 (4)	C9—C8—H8B	110.4
O3—N3—C10	120.3 (3)	H8A—C8—H8B	108.6
O4—N3—C10	116.3 (4)	N1—C9—C8	112.5 (3)
C2—C1—C6	121.0 (3)	N1—C9—H9A	109.1
C2—C1—H1A	119.5	C8—C9—H9A	109.1
C6—C1—H1A	119.5	N1—C9—H9B	109.1
C1—C2—C3	119.6 (4)	C8—C9—H9B	109.1
C1—C2—H2B	120.2	H9A—C9—H9B	107.8
C3—C2—H2B	120.2	C11—C10—N1	107.4 (3)
C4—C3—C2	120.6 (4)	C11—C10—N3	127.8 (3)
C4—C3—H3A	119.7	N1—C10—N3	124.8 (3)
C2—C3—H3A	119.7	N2—C11—C10	109.8 (3)
C5—C4—C3	119.6 (4)	N2—C11—H11A	125.1
C5—C4—H4A	120.2	C10—C11—H11A	125.1
C3—C4—H4A	120.2	N2—C12—N1	112.1 (3)
C4—C5—C6	121.0 (3)	N2—C12—C13	123.8 (3)
C4—C5—Br1	117.1 (3)	N1—C12—C13	124.1 (3)
C6—C5—Br1	121.9 (2)	C12—C13—H13A	109.5
C1—C6—C5	118.0 (3)	C12—C13—H13B	109.5
C1—C6—C7	118.9 (3)	H13A—C13—H13B	109.5
C5—C6—C7	123.0 (3)	C12—C13—H13C	109.5
O1—C7—O2	122.4 (3)	H13A—C13—H13C	109.5
O1—C7—C6	125.9 (3)	H13B—C13—H13C	109.5
C6—C1—C2—C3	−0.9 (6)	C10—N1—C9—C8	80.5 (4)
C1—C2—C3—C4	0.1 (6)	O2—C8—C9—N1	64.2 (4)
C2—C3—C4—C5	0.5 (6)	C12—N1—C10—C11	−0.1 (4)
C3—C4—C5—C6	−0.2 (5)	C9—N1—C10—C11	−177.1 (3)
C3—C4—C5—Br1	−178.1 (3)	C12—N1—C10—N3	−177.7 (3)
C2—C1—C6—C5	1.2 (5)	C9—N1—C10—N3	5.3 (5)
C2—C1—C6—C7	−177.7 (3)	O3—N3—C10—C11	−176.0 (4)
C4—C5—C6—C1	−0.6 (5)	O4—N3—C10—C11	3.1 (6)
Br1—C5—C6—C1	177.1 (3)	O3—N3—C10—N1	1.1 (6)
C4—C5—C6—C7	178.2 (3)	O4—N3—C10—N1	−179.8 (3)
Br1—C5—C6—C7	−4.0 (5)	C12—N2—C11—C10	0.5 (4)
C8—O2—C7—O1	5.6 (5)	N1—C10—C11—N2	−0.2 (4)
C8—O2—C7—C6	−174.4 (3)	N3—C10—C11—N2	177.3 (3)
C1—C6—C7—O1	145.8 (4)	C11—N2—C12—N1	−0.6 (4)
C5—C6—C7—O1	−33.1 (6)	C11—N2—C12—C13	179.9 (3)
C1—C6—C7—O2	−34.2 (4)	C10—N1—C12—N2	0.5 (4)
C5—C6—C7—O2	147.0 (3)	C9—N1—C12—N2	177.6 (3)
C7—O2—C8—C9	156.0 (3)	C10—N1—C12—C13	179.9 (3)
C12—N1—C9—C8	−95.9 (4)	C9—N1—C12—C13	−3.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O4i	0.97	2.51	3.183 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O4i	0.97	2.51	3.183 (4)	127

Symmetry code: (i) .