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

The title compound, C(14)H(9)Cl(3)N(2)O, adopts an E configuration about the methyl-idene unit and the two aromatic rings form a dihedral angle of 6.6 (2)°. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming C(4) chains propagating in [001]. C-H⋯O inter-actions reinforce the chains.

Related literature

For background to hydrazones, see: El-Asmy et al. (2010 ▶); El-Sherif (2009 ▶); Singh et al. (2009 ▶); El-Tabl et al. (2007 ▶). For structures of hydrazone compounds, see: Qiao et al. (2010 ▶); Hussain et al. (2010 ▶); Han & Zhao (2010 ▶); Ahmad et al. (2010 ▶).

Experimental

Crystal data

C14H9Cl3N2O

M = 327.58

Monoclinic,

a = 12.372 (3) Å

b = 14.071 (2) Å

c = 8.332 (2) Å

β = 97.582 (3)°

V = 1437.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.63 mm−1

T = 298 K

0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.833, T max = 0.848

7125 measured reflections

3081 independent reflections

1776 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.129

S = 1.02

3081 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536810051913/hb5766sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051913/hb5766Isup2.hkl

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

C14H9Cl3N2O	F(000) = 664
Mr = 327.58	Dx = 1.513 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.372 (3) Å	Cell parameters from 1072 reflections
b = 14.071 (2) Å	θ = 2.3–25.1°
c = 8.332 (2) Å	µ = 0.63 mm−1
β = 97.582 (3)°	T = 298 K
V = 1437.9 (5) Å3	Cut from needle, colourless
Z = 4	0.30 × 0.27 × 0.27 mm

Bruker SMART CCD diffractometer	3081 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→11
Tmin = 0.833, Tmax = 0.848	k = −17→17
7125 measured reflections	l = −10→10

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.3462P] where P = (Fo2 + 2Fc2)/3
3081 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.34 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	0.50321 (9)	1.17766 (6)	0.13090 (13)	0.0852 (4)
Cl2	0.27379 (8)	1.10398 (6)	0.61537 (13)	0.0791 (3)
Cl3	0.12211 (9)	0.31908 (6)	0.63795 (16)	0.1013 (5)
N1	0.27659 (18)	0.81292 (16)	0.4682 (3)	0.0403 (6)
N2	0.22918 (19)	0.74940 (16)	0.5631 (3)	0.0408 (6)
O1	0.20262 (17)	0.64606 (14)	0.3554 (2)	0.0544 (6)
C1	0.3473 (2)	0.96532 (19)	0.4329 (3)	0.0384 (7)
C2	0.3406 (2)	1.0619 (2)	0.4604 (4)	0.0456 (8)
C3	0.3859 (2)	1.1283 (2)	0.3661 (4)	0.0528 (8)
H3	0.3788	1.1930	0.3845	0.063*
C4	0.4413 (2)	1.0962 (2)	0.2456 (4)	0.0503 (8)
C5	0.4516 (2)	1.0012 (2)	0.2160 (4)	0.0503 (8)
H5	0.4903	0.9805	0.1342	0.060*
C6	0.4041 (2)	0.9370 (2)	0.3086 (3)	0.0435 (7)
H6	0.4102	0.8724	0.2874	0.052*
C7	0.2964 (2)	0.8950 (2)	0.5281 (4)	0.0418 (7)
H7	0.2790	0.9101	0.6302	0.050*
C8	0.1933 (2)	0.66637 (19)	0.4955 (4)	0.0396 (7)
C9	0.1403 (2)	0.59954 (19)	0.5991 (3)	0.0361 (6)
C10	0.1539 (2)	0.5032 (2)	0.5755 (4)	0.0475 (8)
H10	0.1974	0.4820	0.4999	0.057*
C11	0.1030 (3)	0.4393 (2)	0.6640 (4)	0.0582 (9)
C12	0.0359 (3)	0.4696 (3)	0.7725 (4)	0.0723 (11)
H12	0.0004	0.4258	0.8307	0.087*
C13	0.0219 (3)	0.5651 (3)	0.7939 (4)	0.0663 (10)
H13	−0.0235	0.5860	0.8671	0.080*
C14	0.0743 (2)	0.6307 (2)	0.7086 (3)	0.0490 (8)
H14	0.0650	0.6954	0.7250	0.059*
H2	0.227 (2)	0.763 (2)	0.6680 (15)	0.059*

	U11	U22	U33	U12	U13	U23
Cl1	0.1072 (8)	0.0612 (6)	0.0882 (8)	−0.0214 (5)	0.0174 (6)	0.0292 (5)
Cl2	0.0891 (7)	0.0575 (6)	0.0975 (8)	0.0031 (5)	0.0376 (6)	−0.0209 (5)
Cl3	0.1025 (8)	0.0464 (5)	0.1416 (11)	−0.0168 (5)	−0.0342 (7)	0.0293 (6)
N1	0.0504 (14)	0.0348 (13)	0.0360 (15)	−0.0021 (11)	0.0066 (11)	0.0053 (11)
N2	0.0556 (15)	0.0390 (13)	0.0290 (13)	−0.0088 (11)	0.0094 (12)	−0.0006 (12)
O1	0.0815 (15)	0.0482 (12)	0.0366 (13)	−0.0143 (11)	0.0201 (11)	−0.0062 (10)
C1	0.0382 (15)	0.0357 (16)	0.0393 (17)	−0.0020 (13)	−0.0017 (13)	0.0028 (13)
C2	0.0452 (17)	0.0405 (17)	0.050 (2)	0.0006 (13)	0.0034 (14)	−0.0049 (15)
C3	0.0559 (19)	0.0327 (16)	0.066 (2)	−0.0040 (14)	−0.0073 (17)	0.0029 (16)
C4	0.0522 (18)	0.0457 (18)	0.051 (2)	−0.0096 (15)	−0.0022 (16)	0.0176 (16)
C5	0.0604 (19)	0.049 (2)	0.042 (2)	−0.0016 (15)	0.0087 (15)	0.0100 (15)
C6	0.0555 (18)	0.0354 (15)	0.0388 (18)	−0.0012 (13)	0.0025 (14)	0.0029 (14)
C7	0.0488 (17)	0.0427 (17)	0.0336 (17)	−0.0007 (14)	0.0050 (13)	−0.0005 (14)
C8	0.0461 (17)	0.0397 (17)	0.0336 (18)	0.0025 (13)	0.0080 (13)	0.0014 (14)
C9	0.0393 (15)	0.0412 (16)	0.0267 (16)	−0.0059 (13)	0.0007 (12)	0.0022 (13)
C10	0.0417 (16)	0.0453 (18)	0.052 (2)	−0.0023 (13)	−0.0060 (14)	0.0035 (15)
C11	0.060 (2)	0.0458 (19)	0.061 (2)	−0.0173 (16)	−0.0191 (18)	0.0191 (17)
C12	0.074 (2)	0.090 (3)	0.049 (2)	−0.041 (2)	−0.0053 (19)	0.025 (2)
C13	0.058 (2)	0.099 (3)	0.043 (2)	−0.024 (2)	0.0126 (16)	−0.001 (2)
C14	0.0478 (17)	0.062 (2)	0.0370 (18)	−0.0102 (15)	0.0069 (14)	−0.0009 (16)

Cl1—C4	1.733 (3)	C5—C6	1.370 (4)
Cl2—C2	1.728 (3)	C5—H5	0.9300
Cl3—C11	1.726 (3)	C6—H6	0.9300
N1—C7	1.269 (3)	C7—H7	0.9300
N1—N2	1.375 (3)	C8—C9	1.487 (4)
N2—C8	1.347 (3)	C9—C14	1.374 (4)
N2—H2	0.896 (10)	C9—C10	1.383 (4)
O1—C8	1.222 (3)	C10—C11	1.368 (4)
C1—C2	1.382 (4)	C10—H10	0.9300
C1—C6	1.384 (4)	C11—C12	1.373 (5)
C1—C7	1.462 (4)	C12—C13	1.371 (5)
C2—C3	1.386 (4)	C12—H12	0.9300
C3—C4	1.365 (4)	C13—C14	1.377 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.369 (4)	C14—H14	0.9300
C7—N1—N2	116.1 (2)	N1—C7—H7	120.7
C8—N2—N1	117.7 (2)	C1—C7—H7	120.7
C8—N2—H2	122.6 (19)	O1—C8—N2	122.4 (3)
N1—N2—H2	119.5 (19)	O1—C8—C9	120.8 (3)
C2—C1—C6	117.1 (3)	N2—C8—C9	116.8 (3)
C2—C1—C7	122.4 (3)	C14—C9—C10	120.1 (3)
C6—C1—C7	120.5 (3)	C14—C9—C8	122.0 (3)
C1—C2—C3	122.1 (3)	C10—C9—C8	117.8 (3)
C1—C2—Cl2	120.4 (2)	C11—C10—C9	119.6 (3)
C3—C2—Cl2	117.5 (2)	C11—C10—H10	120.2
C4—C3—C2	118.3 (3)	C9—C10—H10	120.2
C4—C3—H3	120.8	C10—C11—C12	120.8 (3)
C2—C3—H3	120.8	C10—C11—Cl3	119.7 (3)
C3—C4—C5	121.5 (3)	C12—C11—Cl3	119.5 (3)
C3—C4—Cl1	119.2 (2)	C13—C12—C11	119.2 (3)
C5—C4—Cl1	119.2 (3)	C13—C12—H12	120.4
C4—C5—C6	119.1 (3)	C11—C12—H12	120.4
C4—C5—H5	120.4	C12—C13—C14	120.9 (3)
C6—C5—H5	120.4	C12—C13—H13	119.5
C5—C6—C1	121.9 (3)	C14—C13—H13	119.5
C5—C6—H6	119.0	C9—C14—C13	119.3 (3)
C1—C6—H6	119.0	C9—C14—H14	120.3
N1—C7—C1	118.5 (3)	C13—C14—H14	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	2.08 (2)	2.900 (3)	152 (3)
C7—H7···O1i	0.93	2.35	3.155 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.90 (1)	2.08 (2)	2.900 (3)	152 (3)
C7—H7⋯O1i	0.93	2.35	3.155 (3)	145

Symmetry code: (i) .