(E)-4-Chloro-N'-(2-chloro-benzyl-idene)benzohydrazide.

The title compound, C(14)H(10)Cl(2)N(2)O, was synthesized by the reaction of 2-chloro-benzaldehyde with an equimolar quantity of 4-chloro-benzohydrazide in methanol. The mol-ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 8.6 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For examples of 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 the n class="Chemical">hydrazone compounds previously reported by our group, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶), Cao & Lu (2009a ▶,b ▶), Cao (2009a ▶,b ▶).

Experimental

Crystal data

C14H10Cl2N2O

M = 293.14

Monoclinic,

a = 10.9140 (4) Å

b = 13.3253 (4) Å

c = 9.1283 (3) Å

β = 96.165 (2)°

V = 1319.87 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.910, T max = 0.918

7970 measured reflections

2863 independent reflections

2099 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.05

2863 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809035739/om2272sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035739/om2272Isup2.hkl

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

C14H10Cl2N2O	F(000) = 600
Mr = 293.14	Dx = 1.475 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2259 reflections
a = 10.9140 (4) Å	θ = 2.4–26.5°
b = 13.3253 (4) Å	µ = 0.48 mm−1
c = 9.1283 (3) Å	T = 298 K
β = 96.165 (2)°	Block, colorless
V = 1319.87 (8) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART 1K diffractometer	2863 independent reflections
Radiation source: fine-focus sealed tube	2099 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→13
Tmin = 0.910, Tmax = 0.918	k = −17→16
7970 measured reflections	l = −11→11

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.3326P] where P = (Fo2 + 2Fc2)/3
2863 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.23 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
Cl1	0.23751 (6)	0.62666 (4)	1.13145 (6)	0.0669 (2)
Cl2	0.45481 (6)	−0.17289 (4)	1.34138 (7)	0.0725 (2)
N1	0.19376 (14)	0.33512 (10)	0.93524 (16)	0.0400 (4)
N2	0.23897 (15)	0.25647 (11)	1.02386 (16)	0.0394 (4)
O1	0.27146 (14)	0.16448 (10)	0.82336 (13)	0.0503 (4)
C1	0.13324 (16)	0.50527 (13)	0.9130 (2)	0.0404 (4)
C2	0.15065 (18)	0.60340 (14)	0.9639 (2)	0.0442 (4)
C3	0.1036 (2)	0.68464 (15)	0.8830 (2)	0.0543 (5)
H3	0.1166	0.7494	0.9193	0.065*
C4	0.0371 (2)	0.66901 (17)	0.7480 (3)	0.0600 (6)
H4	0.0048	0.7234	0.6929	0.072*
C5	0.0185 (2)	0.57327 (17)	0.6945 (2)	0.0586 (6)
H5	−0.0263	0.5630	0.6032	0.070*
C6	0.06591 (18)	0.49246 (15)	0.7758 (2)	0.0487 (5)
H6	0.0527	0.4280	0.7383	0.058*
C7	0.18227 (18)	0.41876 (13)	0.9994 (2)	0.0423 (4)
H7	0.2048	0.4250	1.1002	0.051*
C8	0.27714 (17)	0.17307 (13)	0.95759 (19)	0.0376 (4)
C9	0.32468 (17)	0.08966 (12)	1.05677 (18)	0.0359 (4)
C10	0.37559 (18)	0.10432 (13)	1.20078 (19)	0.0411 (4)
H10	0.3812	0.1688	1.2399	0.049*
C11	0.41803 (19)	0.02376 (14)	1.2864 (2)	0.0477 (5)
H11	0.4537	0.0340	1.3824	0.057*
C12	0.40759 (18)	−0.07139 (14)	1.2298 (2)	0.0456 (5)
C13	0.3595 (2)	−0.08810 (14)	1.0865 (2)	0.0570 (6)
H13	0.3541	−0.1529	1.0484	0.068*
C14	0.3195 (2)	−0.00707 (14)	1.0001 (2)	0.0521 (5)
H14	0.2885	−0.0174	0.9023	0.063*
H2	0.2458 (17)	0.2649 (15)	1.1210 (11)	0.048 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0997 (5)	0.0446 (3)	0.0528 (3)	−0.0018 (3)	−0.0077 (3)	−0.0010 (2)
Cl2	0.0851 (5)	0.0532 (3)	0.0794 (4)	0.0270 (3)	0.0106 (3)	0.0243 (3)
N1	0.0515 (9)	0.0326 (8)	0.0350 (8)	0.0001 (6)	0.0009 (7)	0.0062 (6)
N2	0.0597 (10)	0.0302 (7)	0.0272 (7)	0.0026 (7)	−0.0002 (7)	0.0020 (6)
O1	0.0832 (10)	0.0410 (7)	0.0264 (6)	−0.0001 (6)	0.0039 (6)	−0.0008 (5)
C1	0.0451 (11)	0.0377 (9)	0.0397 (10)	0.0033 (8)	0.0101 (8)	0.0068 (8)
C2	0.0504 (11)	0.0396 (10)	0.0434 (10)	0.0023 (8)	0.0084 (8)	0.0055 (8)
C3	0.0655 (14)	0.0364 (10)	0.0616 (13)	0.0059 (9)	0.0098 (11)	0.0081 (9)
C4	0.0627 (14)	0.0519 (13)	0.0652 (14)	0.0149 (10)	0.0053 (11)	0.0224 (11)
C5	0.0607 (14)	0.0623 (14)	0.0506 (12)	0.0105 (11)	−0.0043 (10)	0.0106 (10)
C6	0.0542 (12)	0.0436 (11)	0.0478 (11)	0.0055 (9)	0.0029 (9)	0.0033 (9)
C7	0.0573 (12)	0.0348 (9)	0.0347 (9)	0.0020 (8)	0.0049 (8)	0.0045 (7)
C8	0.0491 (11)	0.0331 (9)	0.0301 (9)	−0.0065 (7)	0.0014 (8)	0.0004 (7)
C9	0.0449 (10)	0.0305 (8)	0.0328 (9)	−0.0012 (7)	0.0057 (7)	−0.0004 (7)
C10	0.0544 (12)	0.0331 (9)	0.0354 (10)	−0.0001 (8)	0.0023 (8)	−0.0028 (7)
C11	0.0595 (13)	0.0460 (11)	0.0363 (10)	0.0074 (9)	−0.0007 (9)	0.0030 (8)
C12	0.0494 (11)	0.0381 (10)	0.0500 (11)	0.0111 (8)	0.0088 (9)	0.0102 (8)
C13	0.0808 (16)	0.0299 (9)	0.0596 (13)	0.0065 (10)	0.0046 (11)	−0.0057 (9)
C14	0.0780 (15)	0.0385 (10)	0.0379 (11)	0.0037 (10)	−0.0026 (9)	−0.0079 (8)

Cl1—C2	1.739 (2)	C5—C6	1.377 (3)
Cl2—C12	1.7379 (19)	C5—H5	0.9300
N1—C7	1.272 (2)	C6—H6	0.9300
N1—N2	1.3822 (19)	C7—H7	0.9300
N2—C8	1.352 (2)	C8—C9	1.491 (2)
N2—H2	0.889 (9)	C9—C10	1.385 (2)
O1—C8	1.225 (2)	C9—C14	1.388 (2)
C1—C6	1.393 (3)	C10—C11	1.378 (2)
C1—C2	1.394 (3)	C10—H10	0.9300
C1—C7	1.465 (2)	C11—C12	1.369 (3)
C2—C3	1.378 (3)	C11—H11	0.9300
C3—C4	1.377 (3)	C12—C13	1.374 (3)
C3—H3	0.9300	C13—C14	1.380 (3)
C4—C5	1.373 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C7—N1—N2	116.21 (14)	N1—C7—H7	120.3
C8—N2—N1	117.98 (14)	C1—C7—H7	120.3
C8—N2—H2	123.6 (13)	O1—C8—N2	122.62 (16)
N1—N2—H2	118.3 (13)	O1—C8—C9	120.95 (16)
C6—C1—C2	117.03 (17)	N2—C8—C9	116.41 (14)
C6—C1—C7	120.97 (17)	C10—C9—C14	118.77 (16)
C2—C1—C7	122.00 (17)	C10—C9—C8	123.30 (15)
C3—C2—C1	121.92 (19)	C14—C9—C8	117.92 (15)
C3—C2—Cl1	117.90 (16)	C11—C10—C9	120.28 (17)
C1—C2—Cl1	120.15 (14)	C11—C10—H10	119.9
C4—C3—C2	119.4 (2)	C9—C10—H10	119.9
C4—C3—H3	120.3	C12—C11—C10	119.86 (17)
C2—C3—H3	120.3	C12—C11—H11	120.1
C5—C4—C3	120.14 (19)	C10—C11—H11	120.1
C5—C4—H4	119.9	C11—C12—C13	121.14 (17)
C3—C4—H4	119.9	C11—C12—Cl2	119.47 (15)
C4—C5—C6	120.2 (2)	C13—C12—Cl2	119.39 (15)
C4—C5—H5	119.9	C12—C13—C14	118.83 (18)
C6—C5—H5	119.9	C12—C13—H13	120.6
C5—C6—C1	121.34 (19)	C14—C13—H13	120.6
C5—C6—H6	119.3	C13—C14—C9	121.04 (18)
C1—C6—H6	119.3	C13—C14—H14	119.5
N1—C7—C1	119.33 (16)	C9—C14—H14	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.89 (1)	2.07 (1)	2.9157 (18)	160 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.889 (9)	2.065 (11)	2.9157 (18)	159.8 (18)

Symmetry code: (i) .