(E)-3-Bromo-N'-(2,4-dichloro-benzyl-idene)benzohydrazide.

The title compound, C(14)H(9)BrCl(2)N(2)O, was synthesized by the reaction of 2,4-dichloro-benzaldehyde with an equimolar quantity of 3-bromo-benzohydrazide in methanol. The mol-ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 5.3 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Li & Ban (2009 ▶); Zhu et al. (2009 ▶); Yang (2007 ▶); You et al. (2008 ▶). For n class="Chemical">hydrazone compounds reported previously by our group, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶); Cao & Lu (2009a ▶,b ▶); Qu & Cao (2009 ▶); Cao & Wang (2009 ▶); Cao (2009 ▶).

Experimental

Crystal data

C14H9BrCl2N2O

M = 372.04

Monoclinic,

a = 12.140 (2) Å

b = 14.356 (3) Å

c = 8.452 (2) Å

β = 96.019 (3)°

V = 1464.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.17 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.570, T max = 0.600 (expected range = 0.538–0.566)

6615 measured reflections

2350 independent reflections

1561 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.094

S = 1.01

2350 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.76 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030220/ci2871sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030220/ci2871Isup2.hkl

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

C14H9BrCl2N2O	F(000) = 736
Mr = 372.04	Dx = 1.687 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1215 reflections
a = 12.140 (2) Å	θ = 2.2–24.5°
b = 14.356 (3) Å	µ = 3.17 mm−1
c = 8.452 (2) Å	T = 298 K
β = 96.019 (3)°	Block, colourless
V = 1464.9 (5) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2350 independent reflections
Radiation source: fine-focus sealed tube	1561 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 24.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
Tmin = 0.570, Tmax = 0.600	k = −16→15
6615 measured reflections	l = −4→9

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) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.027P)2 + 1.2965P] where P = (Fo2 + 2Fc2)/3
2350 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.64 e Å−3
1 restraint	Δρmin = −0.76 e Å−3

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	0.63560 (5)	0.68952 (3)	0.11003 (7)	0.0796 (3)
Cl1	0.77292 (12)	−0.09489 (8)	0.12692 (16)	0.0724 (4)
Cl2	1.00210 (13)	−0.17858 (10)	−0.36215 (18)	0.0857 (5)
N1	0.7760 (3)	0.1874 (2)	−0.0336 (4)	0.0359 (8)
N2	0.7287 (3)	0.2522 (2)	0.0607 (4)	0.0371 (8)
O1	0.6990 (2)	0.34967 (18)	−0.1509 (3)	0.0505 (8)
C1	0.8471 (3)	0.0368 (3)	−0.0658 (5)	0.0376 (10)
C2	0.8405 (3)	−0.0571 (3)	−0.0332 (5)	0.0422 (10)
C3	0.8859 (4)	−0.1247 (3)	−0.1250 (6)	0.0494 (12)
H3	0.8792	−0.1877	−0.1025	0.059*
C4	0.9409 (4)	−0.0953 (3)	−0.2499 (6)	0.0511 (12)
C5	0.9513 (4)	−0.0029 (3)	−0.2835 (5)	0.0503 (12)
H5	0.9904	0.0157	−0.3670	0.060*
C6	0.9041 (3)	0.0622 (3)	−0.1940 (5)	0.0434 (11)
H6	0.9100	0.1249	−0.2192	0.052*
C7	0.7967 (3)	0.1081 (3)	0.0279 (5)	0.0380 (10)
H7	0.7803	0.0953	0.1307	0.046*
C8	0.6924 (3)	0.3329 (3)	−0.0095 (5)	0.0359 (10)
C9	0.6420 (3)	0.4015 (3)	0.0939 (4)	0.0339 (9)
C10	0.6578 (3)	0.4950 (3)	0.0618 (5)	0.0378 (10)
H10	0.7001	0.5125	−0.0188	0.045*
C11	0.6103 (4)	0.5617 (3)	0.1505 (5)	0.0471 (12)
C12	0.5449 (4)	0.5370 (3)	0.2661 (5)	0.0567 (13)
H12	0.5120	0.5826	0.3237	0.068*
C13	0.5282 (4)	0.4437 (4)	0.2965 (5)	0.0548 (13)
H13	0.4832	0.4266	0.3741	0.066*
C14	0.5781 (3)	0.3756 (3)	0.2123 (5)	0.0422 (11)
H14	0.5685	0.3129	0.2353	0.051*
H2	0.732 (4)	0.243 (3)	0.1660 (16)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0888 (4)	0.0329 (3)	0.1108 (5)	0.0064 (3)	−0.0197 (3)	−0.0116 (3)
Cl1	0.0879 (10)	0.0444 (7)	0.0906 (10)	−0.0053 (7)	0.0363 (8)	0.0120 (7)
Cl2	0.0982 (11)	0.0673 (9)	0.0926 (10)	0.0235 (8)	0.0146 (9)	−0.0379 (8)
N1	0.048 (2)	0.0266 (18)	0.0342 (19)	0.0030 (16)	0.0087 (16)	−0.0037 (16)
N2	0.059 (2)	0.0253 (18)	0.0288 (18)	0.0078 (16)	0.0119 (18)	−0.0020 (16)
O1	0.084 (2)	0.0390 (17)	0.0310 (18)	0.0149 (15)	0.0173 (16)	0.0037 (13)
C1	0.041 (2)	0.034 (2)	0.037 (2)	0.0047 (19)	−0.001 (2)	−0.0054 (19)
C2	0.042 (3)	0.035 (2)	0.049 (3)	0.003 (2)	0.003 (2)	−0.003 (2)
C3	0.050 (3)	0.032 (2)	0.064 (3)	0.004 (2)	−0.003 (3)	−0.007 (2)
C4	0.047 (3)	0.049 (3)	0.056 (3)	0.015 (2)	−0.003 (2)	−0.022 (2)
C5	0.058 (3)	0.048 (3)	0.047 (3)	0.005 (2)	0.011 (2)	−0.010 (2)
C6	0.056 (3)	0.035 (2)	0.039 (3)	0.000 (2)	0.005 (2)	−0.001 (2)
C7	0.050 (3)	0.033 (2)	0.031 (2)	0.001 (2)	0.006 (2)	−0.0001 (19)
C8	0.043 (3)	0.029 (2)	0.036 (3)	−0.0030 (18)	0.007 (2)	−0.0020 (19)
C9	0.040 (2)	0.034 (2)	0.028 (2)	0.0036 (19)	0.0027 (19)	−0.0033 (18)
C10	0.041 (2)	0.032 (2)	0.039 (2)	0.0013 (19)	0.001 (2)	−0.003 (2)
C11	0.055 (3)	0.032 (2)	0.050 (3)	0.011 (2)	−0.013 (2)	−0.009 (2)
C12	0.066 (3)	0.060 (3)	0.043 (3)	0.030 (3)	0.001 (3)	−0.013 (3)
C13	0.050 (3)	0.077 (4)	0.039 (3)	0.019 (3)	0.012 (2)	0.000 (3)
C14	0.047 (3)	0.042 (2)	0.038 (3)	0.005 (2)	0.006 (2)	0.002 (2)

Br1—C11	1.897 (4)	C5—C6	1.365 (5)
Cl1—C2	1.741 (4)	C5—H5	0.93
Cl2—C4	1.740 (4)	C6—H6	0.93
N1—C7	1.265 (4)	C7—H7	0.93
N1—N2	1.388 (4)	C8—C9	1.489 (5)
N2—C8	1.354 (5)	C9—C14	1.380 (5)
N2—H2	0.897 (10)	C9—C10	1.386 (5)
O1—C8	1.230 (4)	C10—C11	1.380 (5)
C1—C2	1.380 (5)	C10—H10	0.93
C1—C6	1.394 (5)	C11—C12	1.369 (6)
C1—C7	1.467 (5)	C12—C13	1.382 (6)
C2—C3	1.391 (6)	C12—H12	0.93
C3—C4	1.374 (6)	C13—C14	1.386 (6)
C3—H3	0.93	C13—H13	0.93
C4—C5	1.365 (6)	C14—H14	0.93
C7—N1—N2	116.3 (3)	N1—C7—H7	120.6
C8—N2—N1	117.2 (3)	C1—C7—H7	120.6
C8—N2—H2	123 (3)	O1—C8—N2	122.8 (3)
N1—N2—H2	119 (3)	O1—C8—C9	120.9 (3)
C2—C1—C6	117.1 (4)	N2—C8—C9	116.3 (3)
C2—C1—C7	122.5 (4)	C14—C9—C10	120.2 (3)
C6—C1—C7	120.4 (4)	C14—C9—C8	123.0 (4)
C1—C2—C3	122.3 (4)	C10—C9—C8	116.8 (4)
C1—C2—Cl1	120.1 (3)	C11—C10—C9	119.5 (4)
C3—C2—Cl1	117.6 (3)	C11—C10—H10	120.3
C4—C3—C2	117.9 (4)	C9—C10—H10	120.3
C4—C3—H3	121.1	C12—C11—C10	121.0 (4)
C2—C3—H3	121.1	C12—C11—Br1	119.7 (3)
C5—C4—C3	121.4 (4)	C10—C11—Br1	119.3 (4)
C5—C4—Cl2	120.0 (4)	C11—C12—C13	119.4 (4)
C3—C4—Cl2	118.5 (4)	C11—C12—H12	120.3
C4—C5—C6	119.8 (4)	C13—C12—H12	120.3
C4—C5—H5	120.1	C12—C13—C14	120.6 (4)
C6—C5—H5	120.1	C12—C13—H13	119.7
C5—C6—C1	121.5 (4)	C14—C13—H13	119.7
C5—C6—H6	119.2	C9—C14—C13	119.4 (4)
C1—C6—H6	119.2	C9—C14—H14	120.3
N1—C7—C1	118.8 (4)	C13—C14—H14	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	2.11 (3)	2.898 (4)	146 (4)
C7—H7···O1i	0.93	2.32	3.134 (5)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.90 (1)	2.11 (3)	2.898 (4)	146 (4)
C7—H7⋯O1i	0.93	2.32	3.134 (5)	146

Symmetry code: (i) .