2-Chloro-N'-(2-chloro-benzyl-idene)benzohydrazide.

The mol-ecule of the title compound, C(14)H(10)Cl(2)N(2)O, adopts an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 79.7 (2)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O, C-H⋯Cl and C-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For the biological activity of hydra­zones, see: Küçükgüzel et al. (2003 ▶); Charkoudian et al. (2007 ▶); Avaji et al. (2009 ▶); Kümmerle et al. (2009 ▶); Raparti et al. (2009 ▶); Bayrak et al. (2009 ▶); Hearn et al. (2009 ▶). For crystal structures of hydrazone compounds, see: Fun et al. (2008 ▶); Lo & Ng (2009 ▶); Ren (2009 ▶); Zhang (2009 ▶); Wu (2009 ▶); Peng & Hou (2008 ▶); Mohd Lair et al. (2009 ▶); Liang & Zou (2009 ▶).

Experimental

Crystal data

C14H10Cl2N2O

M = 293.14

Orthorhombic,

a = 11.9336 (5) Å

b = 9.7471 (4) Å

c = 22.5840 (9) Å

V = 2626.93 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.49 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.897, T max = 0.909

15167 measured reflections

2863 independent reflections

2035 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.098

S = 1.03

2863 reflections

175 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 global, I. DOI: 10.1107/S1600536809043803/ci2943sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043803/ci2943Isup2.hkl

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

C14H10Cl2N2O	F(000) = 1200
Mr = 293.14	Dx = 1.482 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2480 reflections
a = 11.9336 (5) Å	θ = 2.4–24.5°
b = 9.7471 (4) Å	µ = 0.49 mm−1
c = 22.5840 (9) Å	T = 298 K
V = 2626.93 (19) Å3	Block, colourless
Z = 8	0.23 × 0.21 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2863 independent reflections
Radiation source: fine-focus sealed tube	2035 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→11
Tmin = 0.897, Tmax = 0.909	k = −12→12
15167 measured reflections	l = −28→28

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.038P)2 + 0.9372P] where P = (Fo2 + 2Fc2)/3
2863 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.35 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
Cl1	0.79500 (6)	0.47092 (7)	0.48378 (3)	0.0674 (2)
Cl2	0.53369 (5)	1.04300 (6)	0.72070 (3)	0.05271 (18)
N1	0.84153 (13)	0.81563 (16)	0.59949 (6)	0.0345 (4)
N2	0.78786 (14)	0.79951 (16)	0.65338 (7)	0.0341 (4)
O1	0.78386 (13)	1.02813 (13)	0.67114 (6)	0.0445 (4)
C1	0.90227 (16)	0.7097 (2)	0.51022 (8)	0.0352 (4)
C2	0.88637 (17)	0.6053 (2)	0.46878 (9)	0.0413 (5)
C3	0.9388 (2)	0.6077 (3)	0.41454 (10)	0.0540 (6)
H3	0.9271	0.5370	0.3876	0.065*
C4	1.0084 (2)	0.7148 (3)	0.40032 (10)	0.0560 (6)
H4	1.0434	0.7167	0.3635	0.067*
C5	1.02694 (18)	0.8197 (2)	0.44010 (9)	0.0494 (6)
H5	1.0743	0.8920	0.4303	0.059*
C6	0.97447 (17)	0.8163 (2)	0.49456 (9)	0.0415 (5)
H6	0.9876	0.8867	0.5215	0.050*
C7	0.84564 (16)	0.70741 (19)	0.56775 (8)	0.0359 (4)
H7	0.8126	0.6268	0.5812	0.043*
C8	0.76315 (16)	0.91055 (19)	0.68656 (8)	0.0327 (4)
C9	0.71126 (16)	0.87531 (19)	0.74505 (8)	0.0346 (4)
C10	0.61214 (17)	0.9330 (2)	0.76526 (9)	0.0387 (5)
C11	0.5702 (2)	0.9017 (3)	0.82073 (10)	0.0520 (6)
H11	0.5042	0.9422	0.8339	0.062*
C12	0.6263 (2)	0.8106 (3)	0.85620 (10)	0.0600 (7)
H12	0.5982	0.7897	0.8935	0.072*
C13	0.7236 (2)	0.7499 (3)	0.83710 (10)	0.0570 (6)
H13	0.7606	0.6869	0.8611	0.068*
C14	0.76608 (19)	0.7831 (2)	0.78197 (9)	0.0462 (5)
H14	0.8326	0.7430	0.7694	0.055*
H2	0.768 (2)	0.7142 (14)	0.6655 (11)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0867 (5)	0.0575 (4)	0.0581 (4)	−0.0282 (3)	0.0204 (3)	−0.0183 (3)
Cl2	0.0438 (3)	0.0540 (4)	0.0603 (4)	0.0084 (3)	−0.0088 (3)	−0.0094 (3)
N1	0.0413 (9)	0.0334 (9)	0.0288 (8)	0.0033 (7)	0.0049 (7)	0.0008 (7)
N2	0.0447 (10)	0.0279 (8)	0.0297 (8)	0.0004 (7)	0.0066 (7)	−0.0014 (7)
O1	0.0614 (10)	0.0267 (7)	0.0452 (8)	0.0046 (7)	0.0093 (7)	0.0024 (6)
C1	0.0396 (11)	0.0358 (11)	0.0301 (10)	0.0058 (8)	0.0022 (8)	0.0013 (8)
C2	0.0448 (12)	0.0416 (12)	0.0376 (11)	−0.0017 (9)	0.0059 (9)	−0.0040 (9)
C3	0.0608 (15)	0.0597 (15)	0.0415 (12)	−0.0060 (12)	0.0127 (11)	−0.0152 (11)
C4	0.0565 (14)	0.0716 (17)	0.0399 (12)	−0.0003 (12)	0.0174 (11)	−0.0033 (12)
C5	0.0482 (13)	0.0532 (14)	0.0467 (12)	−0.0033 (11)	0.0100 (10)	0.0051 (11)
C6	0.0486 (13)	0.0370 (11)	0.0390 (11)	−0.0009 (9)	0.0038 (9)	0.0007 (9)
C7	0.0452 (11)	0.0308 (10)	0.0318 (10)	0.0007 (9)	0.0034 (8)	0.0015 (8)
C8	0.0354 (10)	0.0285 (10)	0.0341 (10)	0.0027 (8)	−0.0007 (8)	−0.0006 (8)
C9	0.0412 (11)	0.0314 (10)	0.0314 (10)	−0.0012 (8)	0.0024 (8)	−0.0035 (8)
C10	0.0380 (11)	0.0379 (11)	0.0402 (11)	−0.0033 (9)	0.0002 (9)	−0.0109 (9)
C11	0.0460 (13)	0.0633 (15)	0.0467 (13)	−0.0057 (11)	0.0126 (10)	−0.0157 (12)
C12	0.0669 (17)	0.0763 (18)	0.0368 (12)	−0.0104 (14)	0.0154 (12)	0.0003 (12)
C13	0.0686 (16)	0.0625 (15)	0.0398 (12)	0.0039 (13)	0.0043 (11)	0.0107 (11)
C14	0.0535 (13)	0.0460 (13)	0.0391 (11)	0.0066 (10)	0.0070 (10)	0.0025 (10)

Cl1—C2	1.738 (2)	C5—C6	1.381 (3)
Cl2—C10	1.743 (2)	C5—H5	0.93
N1—C7	1.276 (2)	C6—H6	0.93
N1—N2	1.384 (2)	C7—H7	0.93
N2—C8	1.349 (2)	C8—C9	1.499 (3)
N2—H2	0.908 (10)	C9—C10	1.387 (3)
O1—C8	1.223 (2)	C9—C14	1.389 (3)
C1—C6	1.395 (3)	C10—C11	1.383 (3)
C1—C2	1.395 (3)	C11—C12	1.371 (3)
C1—C7	1.465 (3)	C11—H11	0.93
C2—C3	1.376 (3)	C12—C13	1.372 (3)
C3—C4	1.373 (3)	C12—H12	0.93
C3—H3	0.93	C13—C14	1.383 (3)
C4—C5	1.379 (3)	C13—H13	0.93
C4—H4	0.93	C14—H14	0.93
C7—N1—N2	114.69 (16)	N1—C7—H7	119.9
C8—N2—N1	119.89 (15)	C1—C7—H7	119.9
C8—N2—H2	120.6 (17)	O1—C8—N2	123.33 (17)
N1—N2—H2	119.5 (17)	O1—C8—C9	123.31 (17)
C6—C1—C2	117.19 (17)	N2—C8—C9	113.33 (16)
C6—C1—C7	121.43 (18)	C10—C9—C14	117.81 (18)
C2—C1—C7	121.39 (18)	C10—C9—C8	123.31 (17)
C3—C2—C1	121.5 (2)	C14—C9—C8	118.85 (17)
C3—C2—Cl1	118.13 (17)	C11—C10—C9	121.1 (2)
C1—C2—Cl1	120.29 (15)	C11—C10—Cl2	117.69 (17)
C4—C3—C2	119.8 (2)	C9—C10—Cl2	121.17 (15)
C4—C3—H3	120.1	C12—C11—C10	119.7 (2)
C2—C3—H3	120.1	C12—C11—H11	120.1
C3—C4—C5	120.6 (2)	C10—C11—H11	120.1
C3—C4—H4	119.7	C11—C12—C13	120.6 (2)
C5—C4—H4	119.7	C11—C12—H12	119.7
C4—C5—C6	119.3 (2)	C13—C12—H12	119.7
C4—C5—H5	120.3	C12—C13—C14	119.5 (2)
C6—C5—H5	120.3	C12—C13—H13	120.3
C5—C6—C1	121.6 (2)	C14—C13—H13	120.3
C5—C6—H6	119.2	C13—C14—C9	121.3 (2)
C1—C6—H6	119.2	C13—C14—H14	119.4
N1—C7—C1	120.20 (17)	C9—C14—H14	119.4

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.91 (1)	1.92 (1)	2.809 (2)	166 (2)
C7—H7···O1i	0.93	2.53	3.301 (2)	141
C14—H14···Cl2i	0.93	2.75	3.620 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.91 (1)	1.920 (12)	2.809 (2)	166 (2)
C7—H7⋯O1i	0.93	2.53	3.301 (2)	141
C14—H14⋯Cl2i	0.93	2.75	3.620 (2)	156

Symmetry code: (i) .