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

The title compound, C(14)H(10)Cl(2)N(2)O, was prepared from the reaction of 2-chloro-benzaldehyde with 3-chloro-benzo-hydrazide in methanol. The mol-ecule adopts an E configuration about the methyl-idene unit and the two aromatic rings form a dihedral angle of 13.8 (2)°. In the crystal, mol-ecules are linked via inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For background to hydrazones, see: El-Asmy et al. (2010 ▶); El-Sherif (2009 ▶); Singh et al. (2009 ▶); El-Tabl et al. (2007 ▶); Lei (2011 ▶). For structures of hydrazone compounds, see: Qiao et al. (2010 ▶); Hussain et al. (2010 ▶); Han & Zhao (2010 ▶); Ahmad et al. (2010 ▶).

Experimental

Crystal data

C14H10Cl2N2O

M = 293.14

Monoclinic,

a = 13.106 (3) Å

b = 12.588 (3) Å

c = 8.347 (2) Å

β = 97.578 (2)°

V = 1365.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 298 K

0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.865, T max = 0.873

6893 measured reflections

2954 independent reflections

1936 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.01

2954 reflections

175 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.48 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/S1600536811001656/qm2001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001656/qm2001Isup2.hkl

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

C14H10Cl2N2O	F(000) = 600
Mr = 293.14	Dx = 1.426 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.106 (3) Å	Cell parameters from 1672 reflections
b = 12.588 (3) Å	θ = 2.2–25.0°
c = 8.347 (2) Å	µ = 0.47 mm−1
β = 97.578 (2)°	T = 298 K
V = 1365.0 (6) Å3	Cut from needle, colourless
Z = 4	0.32 × 0.30 × 0.30 mm

Bruker SMART CCD area-detector diffractometer	2954 independent reflections
Radiation source: fine-focus sealed tube	1936 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→8
Tmin = 0.865, Tmax = 0.873	k = −15→15
6893 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3
2954 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.48 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	0.21684 (6)	1.16019 (5)	0.46800 (10)	0.0837 (3)
Cl2	0.53314 (6)	0.63298 (7)	0.15637 (9)	0.0856 (3)
N1	0.19380 (12)	0.83421 (13)	0.60855 (18)	0.0400 (4)
N2	0.24735 (13)	0.76623 (13)	0.51905 (19)	0.0427 (4)
O1	0.26043 (12)	0.63872 (10)	0.71199 (17)	0.0540 (4)
C1	0.12399 (14)	1.00751 (15)	0.6282 (2)	0.0385 (5)
C2	0.12993 (16)	1.11524 (18)	0.5925 (3)	0.0490 (5)
C3	0.06753 (19)	1.18886 (19)	0.6553 (3)	0.0611 (6)
H3	0.0727	1.2605	0.6301	0.073*
C4	−0.0017 (2)	1.1565 (2)	0.7544 (3)	0.0632 (7)
H4	−0.0443	1.2059	0.7952	0.076*
C5	−0.00819 (18)	1.0505 (2)	0.7936 (3)	0.0587 (6)
H5	−0.0545	1.0284	0.8622	0.070*
C6	0.05422 (16)	0.97729 (17)	0.7309 (2)	0.0481 (5)
H6	0.0494	0.9060	0.7581	0.058*
C7	0.18546 (15)	0.92841 (16)	0.5543 (2)	0.0421 (5)
H7	0.2187	0.9475	0.4668	0.050*
C8	0.27659 (15)	0.66994 (15)	0.5784 (2)	0.0395 (5)
C9	0.33107 (14)	0.60210 (16)	0.4702 (2)	0.0385 (5)
C10	0.39762 (14)	0.64550 (17)	0.3718 (2)	0.0434 (5)
H10	0.4085	0.7185	0.3701	0.052*
C11	0.44732 (15)	0.57875 (19)	0.2767 (2)	0.0491 (5)
C12	0.43214 (18)	0.4709 (2)	0.2764 (3)	0.0604 (6)
H12	0.4660	0.4271	0.2108	0.073*
C13	0.36611 (18)	0.4287 (2)	0.3747 (3)	0.0597 (6)
H13	0.3549	0.3558	0.3750	0.072*
C14	0.31610 (16)	0.49373 (16)	0.4730 (2)	0.0480 (5)
H14	0.2726	0.4645	0.5406	0.058*
H2	0.2558 (19)	0.784 (2)	0.4177 (15)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0797 (5)	0.0687 (5)	0.1097 (6)	0.0039 (3)	0.0387 (4)	0.0327 (4)
Cl2	0.0801 (5)	0.1113 (6)	0.0754 (5)	0.0101 (4)	0.0480 (4)	0.0065 (4)
N1	0.0445 (9)	0.0439 (10)	0.0329 (9)	0.0052 (7)	0.0100 (7)	−0.0031 (7)
N2	0.0552 (10)	0.0449 (10)	0.0309 (9)	0.0109 (8)	0.0159 (8)	0.0019 (7)
O1	0.0810 (11)	0.0488 (9)	0.0364 (8)	0.0073 (7)	0.0237 (7)	0.0049 (6)
C1	0.0390 (10)	0.0428 (12)	0.0332 (10)	0.0044 (8)	0.0028 (8)	−0.0010 (8)
C2	0.0436 (11)	0.0519 (14)	0.0509 (13)	0.0030 (10)	0.0043 (9)	0.0033 (10)
C3	0.0637 (14)	0.0438 (13)	0.0743 (17)	0.0098 (11)	0.0037 (13)	−0.0032 (12)
C4	0.0640 (15)	0.0614 (16)	0.0644 (16)	0.0179 (12)	0.0092 (13)	−0.0153 (12)
C5	0.0548 (13)	0.0700 (16)	0.0540 (14)	0.0091 (12)	0.0177 (11)	−0.0036 (12)
C6	0.0507 (12)	0.0467 (12)	0.0482 (13)	0.0017 (10)	0.0116 (10)	−0.0008 (10)
C7	0.0435 (11)	0.0482 (12)	0.0357 (11)	0.0037 (9)	0.0098 (8)	0.0013 (9)
C8	0.0427 (11)	0.0438 (12)	0.0331 (11)	0.0010 (9)	0.0092 (8)	0.0002 (9)
C9	0.0376 (10)	0.0452 (12)	0.0323 (10)	0.0052 (8)	0.0033 (8)	−0.0015 (8)
C10	0.0449 (11)	0.0507 (13)	0.0351 (11)	0.0046 (9)	0.0072 (9)	−0.0016 (9)
C11	0.0445 (11)	0.0647 (15)	0.0400 (12)	0.0093 (10)	0.0122 (9)	−0.0011 (10)
C12	0.0610 (14)	0.0699 (17)	0.0511 (14)	0.0208 (12)	0.0102 (12)	−0.0151 (12)
C13	0.0675 (15)	0.0473 (14)	0.0640 (16)	0.0079 (11)	0.0077 (12)	−0.0082 (11)
C14	0.0502 (12)	0.0478 (13)	0.0468 (13)	0.0037 (10)	0.0089 (10)	0.0005 (10)

Cl1—C2	1.735 (2)	C5—C6	1.380 (3)
Cl2—C11	1.743 (2)	C5—H5	0.9300
N1—C7	1.269 (2)	C6—H6	0.9300
N1—N2	1.386 (2)	C7—H7	0.9300
N2—C8	1.346 (2)	C8—C9	1.491 (3)
N2—H2	0.895 (10)	C9—C14	1.379 (3)
O1—C8	1.227 (2)	C9—C10	1.387 (3)
C1—C6	1.387 (3)	C10—C11	1.377 (3)
C1—C2	1.393 (3)	C10—H10	0.9300
C1—C7	1.467 (3)	C11—C12	1.372 (3)
C2—C3	1.384 (3)	C12—C13	1.375 (3)
C3—C4	1.368 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.384 (3)
C4—C5	1.379 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C7—N1—N2	114.25 (16)	N1—C7—H7	119.6
C8—N2—N1	119.83 (15)	C1—C7—H7	119.6
C8—N2—H2	120.5 (17)	O1—C8—N2	123.24 (18)
N1—N2—H2	119.3 (17)	O1—C8—C9	121.38 (18)
C6—C1—C2	117.34 (18)	N2—C8—C9	115.39 (16)
C6—C1—C7	121.13 (18)	C14—C9—C10	120.11 (19)
C2—C1—C7	121.46 (19)	C14—C9—C8	118.42 (18)
C3—C2—C1	121.2 (2)	C10—C9—C8	121.45 (18)
C3—C2—Cl1	118.42 (19)	C11—C10—C9	118.9 (2)
C1—C2—Cl1	120.35 (16)	C11—C10—H10	120.6
C4—C3—C2	120.1 (2)	C9—C10—H10	120.6
C4—C3—H3	119.9	C12—C11—C10	121.7 (2)
C2—C3—H3	119.9	C12—C11—Cl2	119.40 (17)
C3—C4—C5	119.9 (2)	C10—C11—Cl2	118.91 (18)
C3—C4—H4	120.1	C11—C12—C13	118.9 (2)
C5—C4—H4	120.1	C11—C12—H12	120.5
C4—C5—C6	119.9 (2)	C13—C12—H12	120.5
C4—C5—H5	120.1	C12—C13—C14	120.7 (2)
C6—C5—H5	120.1	C12—C13—H13	119.7
C5—C6—C1	121.6 (2)	C14—C13—H13	119.7
C5—C6—H6	119.2	C9—C14—C13	119.7 (2)
C1—C6—H6	119.2	C9—C14—H14	120.1
N1—C7—C1	120.73 (18)	C13—C14—H14	120.1

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	1.98 (1)	2.854 (2)	164 (2)
C7—H7···O1i	0.93	2.51	3.254 (2)	137 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.90 (1)	1.98 (1)	2.854 (2)	164 (2)
C7—H7⋯O1i	0.93	2.51	3.254 (2)	137 (2)

Symmetry code: (i) .