N'-[(E)-1-(4-Bromo-phen-yl)ethyl-idene]-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide.

In the title compound, C(14)H(14)BrN(5)O(3), the mean plane of the imidazole ring (r.m.s deviation = 0.004 Å) forms a dihedral angle of 58.13 (7)° with the benzene ring. In the crystal, mol-ecules are linked via N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds into a three-dimensional network. A short Br⋯Br contact of 3.4932 (2) Å also occurs.

Related literature

For general background to and applications of imidazole derivatives, see: Priya & Kalluraya (2005 ▶); Krapcho & Turk (1966 ▶); Chu et al. (2004 ▶); Khalafi-Nezhad et al. (2005 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H14BrN5O3

M = 380.21

Monoclinic,

a = 8.4176 (1) Å

b = 10.6541 (1) Å

c = 17.4933 (2) Å

β = 90.100 (1)°

V = 1568.83 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.64 mm−1

T = 100 K

0.37 × 0.33 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.441, T max = 0.701

45099 measured reflections

6320 independent reflections

5026 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.02

6320 reflections

214 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.88 e Å−3

Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202795X/rz2774sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202795X/rz2774Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202795X/rz2774Isup3.cml

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

C14H14BrN5O3	F(000) = 768
Mr = 380.21	Dx = 1.610 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9969 reflections
a = 8.4176 (1) Å	θ = 2.3–33.5°
b = 10.6541 (1) Å	µ = 2.64 mm−1
c = 17.4933 (2) Å	T = 100 K
β = 90.100 (1)°	Block, yellow
V = 1568.83 (3) Å3	0.37 × 0.33 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6320 independent reflections
Radiation source: fine-focus sealed tube	5026 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 33.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.441, Tmax = 0.701	k = −16→16
45099 measured reflections	l = −27→27

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.4612P] where P = (Fo2 + 2Fc2)/3
6320 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.88 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.021322 (19)	−0.359303 (13)	0.050226 (9)	0.03144 (5)
O1	0.45656 (12)	0.54105 (9)	0.08914 (5)	0.02360 (19)
O2	0.13283 (13)	0.85764 (9)	0.31753 (6)	0.0269 (2)
O3	−0.04787 (11)	0.73832 (11)	0.26628 (7)	0.0345 (3)
N1	0.33805 (12)	0.23194 (9)	0.05430 (6)	0.01687 (18)
N2	0.40021 (13)	0.34967 (10)	0.04122 (6)	0.01891 (19)
N3	0.31916 (11)	0.50038 (9)	0.22432 (6)	0.01478 (17)
N4	0.36372 (12)	0.68190 (10)	0.28408 (6)	0.01722 (18)
N5	0.09082 (13)	0.76031 (10)	0.28541 (7)	0.0215 (2)
C1	0.29424 (16)	−0.06979 (12)	−0.03559 (7)	0.0221 (2)
H1A	0.3658	−0.0588	−0.0770	0.026*
C2	0.22669 (16)	−0.18701 (12)	−0.02307 (8)	0.0241 (2)
H2A	0.2518	−0.2559	−0.0553	0.029*
C3	0.12217 (16)	−0.20161 (12)	0.03723 (8)	0.0229 (2)
C4	0.08571 (16)	−0.10281 (12)	0.08621 (7)	0.0212 (2)
H4A	0.0153	−0.1149	0.1280	0.025*
C5	0.15433 (14)	0.01392 (11)	0.07288 (7)	0.0184 (2)
H5A	0.1300	0.0822	0.1058	0.022*
C6	0.25865 (14)	0.03226 (11)	0.01173 (7)	0.0181 (2)
C7	0.32849 (15)	0.15744 (11)	−0.00367 (7)	0.0182 (2)
C8	0.40582 (14)	0.43392 (11)	0.09867 (7)	0.0168 (2)
C9	0.35054 (14)	0.39082 (11)	0.17701 (7)	0.0163 (2)
H9A	0.2528	0.3399	0.1719	0.020*
H9B	0.4335	0.3382	0.2012	0.020*
C10	0.17458 (14)	0.55668 (11)	0.23059 (7)	0.0171 (2)
H10A	0.0746	0.5263	0.2134	0.021*
C11	0.20643 (14)	0.66705 (11)	0.26741 (7)	0.0172 (2)
C12	0.43050 (13)	0.57897 (11)	0.25673 (6)	0.01558 (19)
C13	0.38107 (18)	0.19047 (14)	−0.08367 (7)	0.0267 (3)
H13A	0.3421	0.2744	−0.0969	0.040*
H13B	0.3378	0.1290	−0.1198	0.040*
H13C	0.4974	0.1894	−0.0862	0.040*
C14	0.60238 (15)	0.54790 (13)	0.26074 (8)	0.0226 (2)
H14A	0.6556	0.6059	0.2959	0.034*
H14B	0.6494	0.5557	0.2098	0.034*
H14C	0.6155	0.4616	0.2792	0.034*
H1N2	0.436 (2)	0.3704 (17)	0.0004 (12)	0.028 (5)*

	U11	U22	U33	U12	U13	U23
Br1	0.03837 (9)	0.01604 (7)	0.03988 (9)	−0.00786 (5)	−0.01265 (6)	0.00296 (5)
O1	0.0347 (5)	0.0166 (4)	0.0195 (4)	−0.0089 (4)	0.0077 (4)	−0.0024 (3)
O2	0.0300 (5)	0.0167 (4)	0.0342 (5)	0.0039 (3)	0.0041 (4)	−0.0044 (4)
O3	0.0162 (4)	0.0334 (6)	0.0537 (7)	0.0041 (4)	0.0052 (4)	−0.0103 (5)
N1	0.0189 (4)	0.0138 (4)	0.0179 (4)	−0.0020 (3)	0.0007 (3)	−0.0014 (3)
N2	0.0244 (5)	0.0161 (4)	0.0162 (4)	−0.0052 (4)	0.0044 (4)	−0.0017 (4)
N3	0.0153 (4)	0.0130 (4)	0.0160 (4)	−0.0008 (3)	0.0029 (3)	−0.0008 (3)
N4	0.0176 (4)	0.0152 (4)	0.0189 (4)	0.0000 (3)	0.0009 (4)	−0.0017 (3)
N5	0.0204 (5)	0.0181 (5)	0.0261 (5)	0.0030 (4)	0.0068 (4)	0.0003 (4)
C1	0.0245 (6)	0.0194 (5)	0.0222 (5)	0.0008 (4)	−0.0012 (5)	−0.0056 (4)
C2	0.0272 (6)	0.0159 (5)	0.0291 (6)	0.0019 (5)	−0.0055 (5)	−0.0065 (5)
C3	0.0255 (6)	0.0147 (5)	0.0284 (6)	−0.0028 (4)	−0.0095 (5)	0.0003 (4)
C4	0.0241 (6)	0.0183 (5)	0.0212 (5)	−0.0036 (4)	−0.0030 (4)	0.0009 (4)
C5	0.0213 (5)	0.0156 (5)	0.0183 (5)	−0.0013 (4)	−0.0020 (4)	−0.0024 (4)
C6	0.0201 (5)	0.0149 (5)	0.0192 (5)	−0.0007 (4)	−0.0024 (4)	−0.0030 (4)
C7	0.0200 (5)	0.0168 (5)	0.0176 (5)	−0.0017 (4)	0.0007 (4)	−0.0028 (4)
C8	0.0182 (5)	0.0154 (5)	0.0168 (5)	−0.0018 (4)	0.0030 (4)	−0.0012 (4)
C9	0.0199 (5)	0.0116 (4)	0.0175 (5)	−0.0016 (4)	0.0035 (4)	−0.0016 (4)
C10	0.0145 (5)	0.0167 (5)	0.0201 (5)	−0.0011 (4)	0.0033 (4)	0.0007 (4)
C11	0.0172 (5)	0.0148 (5)	0.0197 (5)	0.0011 (4)	0.0040 (4)	−0.0004 (4)
C12	0.0165 (5)	0.0140 (4)	0.0163 (5)	−0.0002 (4)	0.0002 (4)	−0.0004 (4)
C13	0.0371 (7)	0.0252 (6)	0.0178 (5)	−0.0095 (5)	0.0034 (5)	−0.0032 (5)
C14	0.0162 (5)	0.0221 (6)	0.0296 (6)	0.0026 (4)	−0.0041 (5)	−0.0036 (5)

Br1—C3	1.8962 (13)	C3—C4	1.3919 (19)
O1—C8	1.2302 (14)	C4—C5	1.3912 (17)
O2—N5	1.2310 (15)	C4—H4A	0.9500
O3—N5	1.2363 (15)	C5—C6	1.3989 (17)
N1—C7	1.2901 (15)	C5—H5A	0.9500
N1—N2	1.3783 (14)	C6—C7	1.4824 (17)
N2—C8	1.3483 (15)	C7—C13	1.5102 (18)
N2—H1N2	0.81 (2)	C8—C9	1.5190 (16)
N3—C10	1.3614 (15)	C9—H9A	0.9900
N3—C12	1.3779 (15)	C9—H9B	0.9900
N3—C9	1.4554 (15)	C10—C11	1.3671 (17)
N4—C12	1.3223 (15)	C10—H10A	0.9500
N4—C11	1.3644 (16)	C12—C14	1.4857 (16)
N5—C11	1.4264 (15)	C13—H13A	0.9800
C1—C2	1.3898 (19)	C13—H13B	0.9800
C1—C6	1.3992 (17)	C13—H13C	0.9800
C1—H1A	0.9500	C14—H14A	0.9800
C2—C3	1.383 (2)	C14—H14B	0.9800
C2—H2A	0.9500	C14—H14C	0.9800
C7—N1—N2	116.91 (10)	C6—C7—C13	119.67 (10)
C8—N2—N1	119.67 (10)	O1—C8—N2	121.89 (11)
C8—N2—H1N2	117.7 (13)	O1—C8—C9	120.65 (10)
N1—N2—H1N2	122.6 (13)	N2—C8—C9	117.44 (10)
C10—N3—C12	107.86 (9)	N3—C9—C8	109.07 (9)
C10—N3—C9	124.22 (10)	N3—C9—H9A	109.9
C12—N3—C9	126.68 (10)	C8—C9—H9A	109.9
C12—N4—C11	103.86 (10)	N3—C9—H9B	109.9
O2—N5—O3	123.61 (11)	C8—C9—H9B	109.9
O2—N5—C11	119.47 (11)	H9A—C9—H9B	108.3
O3—N5—C11	116.91 (11)	N3—C10—C11	104.02 (10)
C2—C1—C6	121.13 (12)	N3—C10—H10A	128.0
C2—C1—H1A	119.4	C11—C10—H10A	128.0
C6—C1—H1A	119.4	N4—C11—C10	112.94 (10)
C3—C2—C1	118.82 (12)	N4—C11—N5	122.29 (11)
C3—C2—H2A	120.6	C10—C11—N5	124.74 (11)
C1—C2—H2A	120.6	N4—C12—N3	111.32 (10)
C2—C3—C4	121.70 (12)	N4—C12—C14	125.61 (11)
C2—C3—Br1	118.46 (10)	N3—C12—C14	123.07 (10)
C4—C3—Br1	119.80 (11)	C7—C13—H13A	109.5
C5—C4—C3	118.74 (12)	C7—C13—H13B	109.5
C5—C4—H4A	120.6	H13A—C13—H13B	109.5
C3—C4—H4A	120.6	C7—C13—H13C	109.5
C4—C5—C6	120.96 (11)	H13A—C13—H13C	109.5
C4—C5—H5A	119.5	H13B—C13—H13C	109.5
C6—C5—H5A	119.5	C12—C14—H14A	109.5
C5—C6—C1	118.63 (11)	C12—C14—H14B	109.5
C5—C6—C7	120.95 (11)	H14A—C14—H14B	109.5
C1—C6—C7	120.41 (11)	C12—C14—H14C	109.5
N1—C7—C6	115.78 (11)	H14A—C14—H14C	109.5
N1—C7—C13	124.54 (11)	H14B—C14—H14C	109.5
C7—N1—N2—C8	176.66 (12)	C12—N3—C9—C8	−73.37 (14)
C6—C1—C2—C3	0.25 (19)	O1—C8—C9—N3	18.68 (16)
C1—C2—C3—C4	−1.2 (2)	N2—C8—C9—N3	−162.77 (10)
C1—C2—C3—Br1	176.42 (10)	C12—N3—C10—C11	−0.47 (13)
C2—C3—C4—C5	1.3 (2)	C9—N3—C10—C11	−168.42 (10)
Br1—C3—C4—C5	−176.37 (9)	C12—N4—C11—C10	0.27 (14)
C3—C4—C5—C6	−0.28 (19)	C12—N4—C11—N5	−178.11 (11)
C4—C5—C6—C1	−0.66 (18)	N3—C10—C11—N4	0.13 (14)
C4—C5—C6—C7	178.40 (11)	N3—C10—C11—N5	178.47 (11)
C2—C1—C6—C5	0.68 (19)	O2—N5—C11—N4	−0.47 (18)
C2—C1—C6—C7	−178.39 (12)	O3—N5—C11—N4	178.49 (12)
N2—N1—C7—C6	−178.98 (10)	O2—N5—C11—C10	−178.65 (12)
N2—N1—C7—C13	0.29 (18)	O3—N5—C11—C10	0.30 (19)
C5—C6—C7—N1	24.91 (17)	C11—N4—C12—N3	−0.58 (13)
C1—C6—C7—N1	−156.05 (12)	C11—N4—C12—C14	−179.49 (12)
C5—C6—C7—C13	−154.40 (12)	C10—N3—C12—N4	0.69 (13)
C1—C6—C7—C13	24.64 (18)	C9—N3—C12—N4	168.26 (11)
N1—N2—C8—O1	−178.13 (11)	C10—N3—C12—C14	179.63 (11)
N1—N2—C8—C9	3.34 (17)	C9—N3—C12—C14	−12.80 (18)
C10—N3—C9—C8	92.28 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.81 (2)	2.04 (2)	2.8318 (14)	166.6 (18)
C9—H9A···O3ii	0.99	2.31	3.1818 (16)	147
C9—H9B···N4iii	0.99	2.40	3.3462 (16)	160
C10—H10A···O2ii	0.95	2.56	3.4488 (16)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.81 (2)	2.04 (2)	2.8318 (14)	166.6 (18)
C9—H9A⋯O3ii	0.99	2.31	3.1818 (16)	147
C9—H9B⋯N4iii	0.99	2.40	3.3462 (16)	160
C10—H10A⋯O2ii	0.95	2.56	3.4488 (16)	155

Symmetry codes: (i) ; (ii) ; (iii) .