(E)-3-Bromo-N'-(2-chloro-benzyl-idene)benzohydrazide.

The title compound, C(14)H(10)BrClN(2)O, was synthesized by the reaction of 2-chloro-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 13.0 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains propagating 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 hydrazone compounds reported previously by our group, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶); Cao & Lu (2009a ▶,b ▶).

Experimental

Crystal data

C14H10BrClN2O

M = 337.60

Monoclinic,

a = 13.140 (1) Å

b = 12.632 (1) Å

c = 8.377 (1) Å

β = 98.174 (2)°

V = 1376.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.17 mm−1

T = 298 K

0.27 × 0.25 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.481, T max = 0.542 (expected range = 0.442–0.498)

8319 measured reflections

2998 independent reflections

2235 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.076

S = 1.03

2998 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.65 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/S160053680902412X/ci2833sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902412X/ci2833Isup2.hkl

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

C14H10BrClN2O	F(000) = 672
Mr = 337.60	Dx = 1.629 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2981 reflections
a = 13.140 (1) Å	θ = 2.2–27.5°
b = 12.632 (1) Å	µ = 3.17 mm−1
c = 8.377 (1) Å	T = 298 K
β = 98.174 (2)°	Block, colourless
V = 1376.3 (2) Å3	0.27 × 0.25 × 0.22 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2998 independent reflections
Radiation source: fine-focus sealed tube	2235 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→15
Tmin = 0.481, Tmax = 0.542	k = −16→13
8319 measured reflections	l = −10→10

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0266P)2 + 0.7889P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2998 reflections	Δρmax = 0.52 e Å−3
176 parameters	Δρmin = −0.65 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0155 (8)

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	1.03493 (2)	0.63367 (3)	0.15480 (4)	0.06855 (15)
Cl1	0.71461 (6)	1.15851 (6)	0.46918 (11)	0.0757 (3)
N1	0.69113 (14)	0.83453 (15)	0.6106 (2)	0.0358 (4)
N2	0.74414 (15)	0.76627 (15)	0.5225 (2)	0.0378 (4)
O1	0.75662 (14)	0.64019 (12)	0.71573 (18)	0.0477 (4)
C1	0.62315 (16)	1.00731 (17)	0.6291 (3)	0.0342 (5)
C2	0.62851 (18)	1.11440 (19)	0.5940 (3)	0.0433 (6)
C3	0.5678 (2)	1.1884 (2)	0.6563 (3)	0.0542 (7)
H3	0.5732	1.2596	0.6310	0.065*
C4	0.4996 (2)	1.1563 (2)	0.7553 (3)	0.0572 (7)
H4	0.4581	1.2057	0.7970	0.069*
C5	0.4924 (2)	1.0510 (2)	0.7933 (3)	0.0523 (7)
H5	0.4459	1.0293	0.8607	0.063*
C6	0.55369 (18)	0.9775 (2)	0.7319 (3)	0.0429 (6)
H6	0.5487	0.9066	0.7596	0.052*
C7	0.68317 (17)	0.92838 (18)	0.5560 (3)	0.0367 (5)
H7	0.7159	0.9469	0.4686	0.044*
C8	0.77228 (16)	0.67075 (17)	0.5825 (2)	0.0336 (5)
C9	0.82605 (15)	0.60205 (17)	0.4763 (2)	0.0319 (5)
C10	0.89265 (16)	0.64395 (18)	0.3775 (3)	0.0359 (5)
H10	0.9036	0.7166	0.3742	0.043*
C11	0.94190 (17)	0.5767 (2)	0.2851 (3)	0.0395 (5)
C12	0.9267 (2)	0.4693 (2)	0.2864 (3)	0.0487 (6)
H12	0.9603	0.4249	0.2225	0.058*
C13	0.8606 (2)	0.4287 (2)	0.3844 (3)	0.0498 (6)
H13	0.8490	0.3561	0.3859	0.060*
C14	0.81123 (18)	0.49435 (18)	0.4804 (3)	0.0411 (5)
H14	0.7679	0.4658	0.5479	0.049*
H2	0.749 (2)	0.784 (2)	0.4206 (17)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0647 (2)	0.0867 (3)	0.0630 (2)	0.00759 (16)	0.03940 (15)	0.00891 (15)
Cl1	0.0682 (5)	0.0610 (5)	0.1056 (6)	0.0046 (4)	0.0393 (4)	0.0307 (4)
N1	0.0373 (10)	0.0395 (11)	0.0326 (9)	0.0065 (8)	0.0121 (8)	−0.0033 (8)
N2	0.0477 (11)	0.0400 (11)	0.0292 (9)	0.0105 (9)	0.0168 (8)	0.0004 (8)
O1	0.0696 (12)	0.0445 (10)	0.0339 (8)	0.0059 (8)	0.0236 (8)	0.0038 (7)
C1	0.0307 (11)	0.0393 (12)	0.0322 (11)	0.0033 (9)	0.0031 (9)	−0.0017 (9)
C2	0.0375 (12)	0.0439 (14)	0.0487 (14)	0.0022 (10)	0.0063 (10)	0.0019 (10)
C3	0.0551 (15)	0.0383 (14)	0.0686 (18)	0.0081 (12)	0.0063 (14)	−0.0028 (12)
C4	0.0551 (16)	0.0562 (17)	0.0609 (17)	0.0170 (13)	0.0102 (14)	−0.0140 (13)
C5	0.0474 (14)	0.0642 (18)	0.0484 (15)	0.0073 (13)	0.0175 (12)	−0.0042 (13)
C6	0.0429 (13)	0.0435 (14)	0.0443 (13)	0.0035 (11)	0.0127 (11)	−0.0016 (11)
C7	0.0383 (12)	0.0423 (14)	0.0314 (11)	0.0033 (10)	0.0114 (9)	0.0015 (10)
C8	0.0352 (11)	0.0369 (12)	0.0300 (11)	0.0002 (9)	0.0096 (9)	−0.0022 (9)
C9	0.0297 (11)	0.0382 (12)	0.0280 (10)	0.0051 (9)	0.0049 (8)	0.0002 (9)
C10	0.0369 (12)	0.0392 (12)	0.0329 (11)	0.0027 (10)	0.0088 (9)	−0.0006 (9)
C11	0.0341 (11)	0.0526 (15)	0.0336 (11)	0.0064 (10)	0.0112 (9)	0.0018 (10)
C12	0.0508 (14)	0.0518 (16)	0.0450 (14)	0.0149 (12)	0.0119 (11)	−0.0089 (12)
C13	0.0573 (15)	0.0353 (13)	0.0576 (15)	0.0054 (12)	0.0114 (12)	−0.0040 (11)
C14	0.0410 (13)	0.0413 (14)	0.0427 (13)	0.0021 (10)	0.0120 (10)	0.0025 (10)

Br1—C11	1.892 (2)	C5—C6	1.376 (3)
Cl1—C2	1.738 (2)	C5—H5	0.93
N1—C7	1.270 (3)	C6—H6	0.93
N1—N2	1.386 (2)	C7—H7	0.93
N2—C8	1.339 (3)	C8—C9	1.491 (3)
N2—H2	0.893 (10)	C9—C14	1.376 (3)
O1—C8	1.226 (2)	C9—C10	1.392 (3)
C1—C2	1.388 (3)	C10—C11	1.372 (3)
C1—C6	1.393 (3)	C10—H10	0.93
C1—C7	1.459 (3)	C11—C12	1.372 (4)
C2—C3	1.378 (3)	C12—C13	1.376 (4)
C3—C4	1.366 (4)	C12—H12	0.93
C3—H3	0.93	C13—C14	1.379 (3)
C4—C5	1.374 (4)	C13—H13	0.93
C4—H4	0.93	C14—H14	0.93
C7—N1—N2	114.24 (17)	N1—C7—H7	119.7
C8—N2—N1	119.58 (17)	C1—C7—H7	119.7
C8—N2—H2	122 (2)	O1—C8—N2	123.53 (19)
N1—N2—H2	118 (2)	O1—C8—C9	121.02 (19)
C2—C1—C6	116.9 (2)	N2—C8—C9	115.44 (18)
C2—C1—C7	122.0 (2)	C14—C9—C10	119.6 (2)
C6—C1—C7	121.1 (2)	C14—C9—C8	118.69 (19)
C3—C2—C1	122.1 (2)	C10—C9—C8	121.7 (2)
C3—C2—Cl1	118.1 (2)	C11—C10—C9	119.2 (2)
C1—C2—Cl1	119.79 (18)	C11—C10—H10	120.4
C4—C3—C2	119.6 (2)	C9—C10—H10	120.4
C4—C3—H3	120.2	C10—C11—C12	121.8 (2)
C2—C3—H3	120.2	C10—C11—Br1	119.05 (18)
C3—C4—C5	120.1 (2)	C12—C11—Br1	119.17 (17)
C3—C4—H4	120.0	C11—C12—C13	118.6 (2)
C5—C4—H4	120.0	C11—C12—H12	120.7
C4—C5—C6	120.2 (2)	C13—C12—H12	120.7
C4—C5—H5	119.9	C12—C13—C14	120.8 (2)
C6—C5—H5	119.9	C12—C13—H13	119.6
C5—C6—C1	121.3 (2)	C14—C13—H13	119.6
C5—C6—H6	119.4	C9—C14—C13	120.0 (2)
C1—C6—H6	119.4	C9—C14—H14	120.0
N1—C7—C1	120.54 (19)	C13—C14—H14	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.89 (1)	1.98 (1)	2.854 (2)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.89 (1)	1.98 (1)	2.854 (2)	165 (3)

Symmetry code: (i) .