2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-bromo-benzoate.

The mol-ecule of the title compound, C(13)H(12)BrN(3)O(4), is non-planar, as indicated in the dihedral angle of 59.5 (4)° formed between the least-squares planes through the imidazole and benzene rings. In the crystal, mol-ecules are connected via C-H⋯O contacts, forming a supra-molecular chain.

Related literature

For potential pharmacological uses of benzoic acid derivatives, see: Correa-Basurto et al. (2005 ▶); Jetten et al. (1987 ▶); Kelly et al. (2007 ▶); Sato et al. (2005 ▶). For a related structure, see: Wang et al. (2008 ▶).

Experimental

Crystal data

C13H12BrN3O4

M = 354.17

Monoclinic,

a = 11.871 (2) Å

b = 19.840 (4) Å

c = 7.1983 (13) Å

β = 124.488 (3)°

V = 1397.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.96 mm−1

T = 150 K

0.20 × 0.07 × 0.03 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.589, T max = 0.916

5456 measured reflections

2680 independent reflections

1636 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.119

S = 0.86

2680 reflections

191 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.55 e Å−3

Absolute structure: Flack (1983 ▶), 1301 Friedel pairs

Flack parameter: 0.091 (17)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015499/tk2425sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015499/tk2425Isup2.hkl

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

C13H12BrN3O4	F(000) = 712
Mr = 354.17	Dx = 1.683 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 616 reflections
a = 11.871 (2) Å	θ = 3.7–23.3°
b = 19.840 (4) Å	µ = 2.96 mm−1
c = 7.1983 (13) Å	T = 150 K
β = 124.488 (3)°	Needle, colourless
V = 1397.4 (4) Å3	0.20 × 0.07 × 0.03 mm
Z = 4

Bruker APEX 2000 CCD area-detector diffractometer	2680 independent reflections
Radiation source: fine-focus sealed tube	1636 reflections with I > 2σ(I)
graphite	Rint = 0.087
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.589, Tmax = 0.916	k = −24→23
5456 measured reflections	l = −8→8

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)] = 0.061	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0345P)2] where P = (Fo2 + 2Fc2)/3
S = 0.86	(Δ/σ)max = 0.001
2680 reflections	Δρmax = 0.66 e Å−3
191 parameters	Δρmin = −0.55 e Å−3
2 restraints	Absolute structure: Flack (1983), 1301 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.091 (17)

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	0.81001 (10)	0.59782 (5)	0.72927 (13)	0.0588 (3)
O1	0.0138 (5)	0.6343 (3)	0.5323 (9)	0.0363 (14)
O2	0.0896 (5)	0.7074 (3)	0.8019 (9)	0.0434 (15)
O3	0.2933 (5)	0.5475 (3)	0.4184 (9)	0.0309 (14)
O4	0.2623 (6)	0.4375 (3)	0.4381 (11)	0.0437 (16)
N1	0.0966 (6)	0.6786 (3)	0.6597 (11)	0.0322 (16)
N2	0.2152 (6)	0.6769 (3)	0.4669 (9)	0.0234 (14)
N3	0.3904 (6)	0.7449 (3)	0.6962 (11)	0.0324 (16)
C1	0.2023 (8)	0.6976 (4)	0.6362 (12)	0.0261 (17)
C2	0.3074 (10)	0.7391 (4)	0.7650 (18)	0.042 (3)
H2	0.3216	0.7622	0.8924	0.050*
C3	0.3307 (8)	0.7090 (4)	0.5099 (13)	0.0281 (18)
C4	0.1261 (7)	0.6329 (4)	0.2730 (12)	0.0280 (18)
H4A	0.1413	0.6422	0.1537	0.034*
H4B	0.0295	0.6436	0.2115	0.034*
C5	0.1513 (7)	0.5597 (4)	0.3332 (13)	0.0294 (19)
H5A	0.1344	0.5490	0.4498	0.035*
H5B	0.0903	0.5315	0.1988	0.035*
C6	0.3328 (8)	0.4832 (4)	0.4592 (12)	0.0222 (18)
C7	0.4765 (8)	0.4759 (4)	0.5349 (12)	0.0263 (19)
C8	0.5272 (9)	0.4134 (4)	0.5409 (13)	0.041 (2)
H8	0.4686	0.3754	0.4966	0.049*
C9	0.6614 (10)	0.4036 (5)	0.6098 (14)	0.048 (2)
H9	0.6962	0.3596	0.6198	0.057*
C10	0.7422 (9)	0.4597 (5)	0.6630 (13)	0.049 (3)
H10	0.8333	0.4538	0.7053	0.059*
C11	0.6978 (8)	0.5231 (4)	0.6579 (12)	0.035 (2)
C12	0.5625 (7)	0.5325 (4)	0.5850 (12)	0.032 (2)
H12	0.5277	0.5768	0.5688	0.038*
C13	0.3796 (8)	0.7029 (4)	0.3597 (13)	0.043 (2)
H13A	0.3319	0.7359	0.2373	0.064*
H13B	0.3608	0.6573	0.2962	0.064*
H13C	0.4781	0.7115	0.4472	0.064*

	U11	U22	U33	U12	U13	U23
Br1	0.0321 (4)	0.0955 (8)	0.0384 (5)	−0.0218 (7)	0.0137 (4)	0.0017 (7)
O1	0.025 (3)	0.046 (4)	0.035 (3)	−0.002 (3)	0.014 (3)	0.006 (3)
O2	0.038 (3)	0.065 (4)	0.039 (3)	0.001 (3)	0.028 (3)	−0.007 (3)
O3	0.025 (3)	0.031 (3)	0.036 (4)	0.002 (3)	0.017 (3)	0.005 (3)
O4	0.042 (4)	0.031 (3)	0.062 (4)	−0.003 (3)	0.032 (4)	0.005 (3)
N1	0.021 (4)	0.044 (4)	0.030 (4)	0.007 (3)	0.014 (3)	0.013 (3)
N2	0.025 (4)	0.028 (4)	0.018 (3)	−0.009 (3)	0.012 (3)	−0.003 (3)
N3	0.031 (4)	0.036 (4)	0.036 (4)	−0.007 (3)	0.022 (4)	−0.012 (3)
C1	0.024 (4)	0.031 (4)	0.025 (4)	−0.005 (4)	0.015 (4)	−0.006 (4)
C2	0.030 (5)	0.030 (5)	0.059 (7)	0.003 (5)	0.021 (5)	0.000 (5)
C3	0.035 (5)	0.024 (4)	0.030 (5)	0.006 (4)	0.021 (4)	0.008 (4)
C4	0.027 (4)	0.039 (5)	0.022 (4)	−0.005 (4)	0.017 (4)	0.000 (4)
C5	0.021 (4)	0.043 (5)	0.028 (5)	−0.003 (4)	0.017 (4)	0.008 (4)
C6	0.027 (5)	0.028 (5)	0.010 (4)	−0.004 (4)	0.010 (3)	−0.002 (4)
C7	0.024 (4)	0.037 (5)	0.019 (4)	0.005 (4)	0.013 (4)	−0.002 (4)
C8	0.044 (6)	0.046 (6)	0.024 (5)	0.004 (5)	0.014 (4)	0.003 (4)
C9	0.049 (6)	0.049 (6)	0.041 (6)	0.022 (5)	0.023 (5)	0.011 (5)
C10	0.038 (5)	0.085 (8)	0.035 (6)	0.012 (5)	0.027 (5)	0.012 (5)
C11	0.029 (5)	0.050 (6)	0.021 (4)	0.005 (4)	0.011 (4)	0.000 (4)
C12	0.025 (4)	0.045 (5)	0.021 (4)	0.009 (4)	0.010 (4)	0.009 (4)
C13	0.053 (6)	0.043 (5)	0.044 (5)	−0.010 (5)	0.035 (5)	0.006 (4)

Br1—C11	1.861 (8)	C4—H4B	0.9900
O1—N1	1.248 (7)	C5—H5A	0.9900
O2—N1	1.216 (8)	C5—H5B	0.9900
O3—C6	1.334 (9)	C6—C7	1.475 (10)
O3—C5	1.451 (8)	C7—C8	1.369 (10)
O4—C6	1.183 (9)	C7—C12	1.420 (11)
N1—C1	1.410 (9)	C8—C9	1.389 (12)
N2—C1	1.374 (9)	C8—H8	0.9500
N2—C3	1.378 (9)	C9—C10	1.375 (11)
N2—C4	1.468 (8)	C9—H9	0.9500
N3—C3	1.317 (9)	C10—C11	1.356 (11)
N3—C2	1.334 (11)	C10—H10	0.9500
C1—C2	1.336 (12)	C11—C12	1.391 (10)
C2—H2	0.9500	C12—H12	0.9500
C3—C13	1.493 (10)	C13—H13A	0.9800
C4—C5	1.497 (10)	C13—H13B	0.9800
C4—H4A	0.9900	C13—H13C	0.9800
C6—O3—C5	115.6 (6)	H5A—C5—H5B	108.7
O2—N1—O1	123.3 (6)	O4—C6—O3	124.8 (7)
O2—N1—C1	117.7 (7)	O4—C6—C7	124.0 (8)
O1—N1—C1	119.0 (6)	O3—C6—C7	111.3 (7)
C1—N2—C3	105.0 (6)	C8—C7—C12	118.0 (7)
C1—N2—C4	129.7 (6)	C8—C7—C6	119.7 (8)
C3—N2—C4	125.2 (6)	C12—C7—C6	122.1 (7)
C3—N3—C2	104.3 (7)	C7—C8—C9	122.2 (8)
C2—C1—N2	105.7 (7)	C7—C8—H8	118.9
C2—C1—N1	128.8 (8)	C9—C8—H8	118.9
N2—C1—N1	125.4 (6)	C10—C9—C8	117.7 (8)
N3—C2—C1	113.0 (9)	C10—C9—H9	121.1
N3—C2—H2	123.5	C8—C9—H9	121.1
C1—C2—H2	123.5	C11—C10—C9	122.9 (8)
N3—C3—N2	111.8 (6)	C11—C10—H10	118.5
N3—C3—C13	125.1 (7)	C9—C10—H10	118.5
N2—C3—C13	123.0 (7)	C10—C11—C12	118.9 (8)
N2—C4—C5	112.5 (6)	C10—C11—Br1	121.6 (7)
N2—C4—H4A	109.1	C12—C11—Br1	119.3 (6)
C5—C4—H4A	109.1	C11—C12—C7	120.0 (8)
N2—C4—H4B	109.1	C11—C12—H12	120.0
C5—C4—H4B	109.1	C7—C12—H12	120.0
H4A—C4—H4B	107.8	C3—C13—H13A	109.5
O3—C5—C4	106.1 (6)	C3—C13—H13B	109.5
O3—C5—H5A	110.5	H13A—C13—H13B	109.5
C4—C5—H5A	110.5	C3—C13—H13C	109.5
O3—C5—H5B	110.5	H13A—C13—H13C	109.5
C4—C5—H5B	110.5	H13B—C13—H13C	109.5
C3—N2—C1—C2	−0.1 (8)	C6—O3—C5—C4	−173.1 (6)
C4—N2—C1—C2	−177.6 (7)	N2—C4—C5—O3	−59.7 (7)
C3—N2—C1—N1	178.8 (7)	C5—O3—C6—O4	−2.7 (11)
C4—N2—C1—N1	1.3 (12)	C5—O3—C6—C7	177.4 (6)
O2—N1—C1—C2	7.5 (12)	O4—C6—C7—C8	13.3 (12)
O1—N1—C1—C2	−173.8 (8)	O3—C6—C7—C8	−166.7 (7)
O2—N1—C1—N2	−171.2 (7)	O4—C6—C7—C12	−172.0 (7)
O1—N1—C1—N2	7.5 (10)	O3—C6—C7—C12	8.0 (10)
C3—N3—C2—C1	3.8 (10)	C12—C7—C8—C9	4.8 (12)
N2—C1—C2—N3	−2.3 (10)	C6—C7—C8—C9	179.8 (7)
N1—C1—C2—N3	178.8 (7)	C7—C8—C9—C10	−3.0 (13)
C2—N3—C3—N2	−3.8 (9)	C8—C9—C10—C11	2.2 (13)
C2—N3—C3—C13	176.0 (8)	C9—C10—C11—C12	−3.3 (13)
C1—N2—C3—N3	2.5 (8)	C9—C10—C11—Br1	−179.6 (6)
C4—N2—C3—N3	−179.8 (6)	C10—C11—C12—C7	5.1 (11)
C1—N2—C3—C13	−177.3 (7)	Br1—C11—C12—C7	−178.5 (6)
C4—N2—C3—C13	0.3 (11)	C8—C7—C12—C11	−5.8 (11)
C1—N2—C4—C5	−81.4 (9)	C6—C7—C12—C11	179.4 (7)
C3—N2—C4—C5	101.6 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4a···O2i	0.99	2.59	3.494 (10)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4a⋯O2i	0.99	2.59	3.494 (10)	152

Symmetry code: (i) .