N'-(2,4-Dichloro-benzyl-idene)-2-methyl-benzohydrazide.

In the title hydrazone compound, C(15)H(12)Cl(2)N(2)O, the dihedral angle between the two benzene rings is 12.2 (2)°. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming forming C(4) chains propagating in [001].

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For the crystal structures of related compounds, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12Cl2N2O

M = 307.17

Monoclinic,

a = 7.563 (1) Å

b = 25.729 (2) Å

c = 8.174 (2) Å

β = 115.771 (2)°

V = 1432.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 298 K

0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.936, T max = 0.957

7436 measured reflections

3040 independent reflections

1529 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.097

S = 0.85

3040 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043710/wn2414sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043710/wn2414Isup2.hkl

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

C15H12Cl2N2O	F(000) = 632
Mr = 307.17	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.563 (1) Å	Cell parameters from 1160 reflections
b = 25.729 (2) Å	θ = 2.7–24.3°
c = 8.174 (2) Å	µ = 0.45 mm−1
β = 115.771 (2)°	T = 298 K
V = 1432.4 (4) Å3	Block, colourless
Z = 4	0.15 × 0.13 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3040 independent reflections
Radiation source: fine-focus sealed tube	1529 reflections with I > 2σ(I)
graphite	Rint = 0.089
ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→6
Tmin = 0.936, Tmax = 0.957	k = −32→28
7436 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ2(Fo2) + (0.0246P)2] where P = (Fo2 + 2Fc2)/3
3040 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.18 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	0.30785 (12)	0.05472 (3)	0.66289 (10)	0.0762 (3)
Cl2	−0.23133 (11)	0.02731 (3)	−0.01806 (10)	0.0694 (3)
H2	0.424 (4)	0.2371 (10)	0.803 (2)	0.080*
N1	0.3080 (3)	0.21618 (9)	0.5418 (2)	0.0400 (5)
N2	0.4152 (3)	0.24626 (9)	0.6931 (3)	0.0412 (6)
O1	0.4719 (3)	0.30767 (7)	0.5227 (2)	0.0506 (5)
C1	0.1513 (3)	0.13548 (10)	0.4312 (3)	0.0354 (6)
C2	0.1547 (3)	0.08202 (11)	0.4558 (3)	0.0411 (7)
C3	0.0400 (4)	0.04854 (11)	0.3178 (3)	0.0455 (7)
H3	0.0474	0.0128	0.3363	0.055*
C4	−0.0840 (3)	0.06916 (12)	0.1541 (3)	0.0422 (7)
C5	−0.0965 (4)	0.12162 (12)	0.1234 (3)	0.0473 (7)
H5	−0.1832	0.1350	0.0114	0.057*
C6	0.0214 (4)	0.15428 (11)	0.2613 (3)	0.0438 (7)
H6	0.0142	0.1899	0.2403	0.053*
C7	0.2715 (3)	0.17057 (11)	0.5775 (3)	0.0392 (7)
H7	0.3215	0.1595	0.6976	0.047*
C8	0.4929 (4)	0.29150 (10)	0.6711 (3)	0.0375 (6)
C9	0.6141 (4)	0.31927 (10)	0.8446 (3)	0.0367 (6)
C10	0.5972 (4)	0.37312 (11)	0.8577 (3)	0.0419 (7)
C11	0.7197 (5)	0.39632 (12)	1.0223 (4)	0.0587 (8)
H11	0.7096	0.4320	1.0353	0.070*
C12	0.8536 (5)	0.36888 (15)	1.1652 (4)	0.0649 (9)
H12	0.9344	0.3859	1.2720	0.078*
C13	0.8691 (4)	0.31614 (14)	1.1512 (4)	0.0601 (9)
H13	0.9602	0.2972	1.2482	0.072*
C14	0.7481 (4)	0.29148 (11)	0.9917 (3)	0.0472 (7)
H14	0.7564	0.2556	0.9827	0.057*
C15	0.4557 (4)	0.40581 (11)	0.7048 (4)	0.0604 (9)
H15A	0.4380	0.4386	0.7516	0.091*
H15B	0.3317	0.3882	0.6475	0.091*
H15C	0.5068	0.4115	0.6174	0.091*

	U11	U22	U33	U12	U13	U23
Cl1	0.0772 (6)	0.0571 (6)	0.0563 (5)	−0.0056 (4)	−0.0065 (4)	0.0130 (4)
Cl2	0.0518 (5)	0.0768 (6)	0.0616 (5)	−0.0099 (4)	0.0080 (4)	−0.0297 (4)
N1	0.0466 (14)	0.0428 (15)	0.0341 (12)	−0.0087 (12)	0.0208 (10)	−0.0055 (11)
N2	0.0559 (14)	0.0402 (15)	0.0316 (12)	−0.0128 (12)	0.0229 (12)	−0.0057 (11)
O1	0.0797 (14)	0.0437 (13)	0.0342 (10)	−0.0083 (10)	0.0301 (10)	0.0013 (8)
C1	0.0309 (14)	0.0418 (18)	0.0359 (15)	−0.0042 (13)	0.0169 (12)	−0.0042 (12)
C2	0.0340 (15)	0.0457 (19)	0.0390 (15)	−0.0025 (13)	0.0116 (12)	−0.0008 (13)
C3	0.0380 (16)	0.0406 (19)	0.0550 (17)	−0.0034 (13)	0.0175 (14)	−0.0038 (14)
C4	0.0309 (15)	0.051 (2)	0.0421 (16)	−0.0033 (13)	0.0134 (13)	−0.0131 (14)
C5	0.0403 (16)	0.062 (2)	0.0339 (15)	0.0094 (15)	0.0113 (13)	−0.0041 (14)
C6	0.0496 (17)	0.0418 (19)	0.0391 (16)	0.0049 (14)	0.0185 (14)	0.0018 (13)
C7	0.0411 (16)	0.0446 (19)	0.0303 (14)	−0.0041 (14)	0.0139 (12)	−0.0009 (13)
C8	0.0429 (16)	0.0371 (18)	0.0369 (15)	0.0020 (13)	0.0213 (13)	−0.0031 (13)
C9	0.0420 (16)	0.0399 (19)	0.0355 (15)	−0.0059 (13)	0.0236 (13)	−0.0013 (12)
C10	0.0492 (17)	0.0383 (19)	0.0520 (17)	−0.0061 (14)	0.0348 (15)	−0.0031 (14)
C11	0.076 (2)	0.050 (2)	0.066 (2)	−0.0191 (18)	0.046 (2)	−0.0198 (18)
C12	0.074 (2)	0.079 (3)	0.0475 (19)	−0.032 (2)	0.0317 (19)	−0.0183 (19)
C13	0.056 (2)	0.077 (3)	0.0438 (18)	−0.0152 (18)	0.0183 (16)	0.0042 (17)
C14	0.0507 (17)	0.0504 (19)	0.0431 (16)	−0.0092 (15)	0.0228 (14)	−0.0014 (15)
C15	0.065 (2)	0.043 (2)	0.079 (2)	0.0056 (16)	0.0376 (19)	0.0034 (17)

Cl1—C2	1.731 (2)	C7—H7	0.9300
Cl2—C4	1.737 (2)	C8—C9	1.494 (3)
N1—C7	1.268 (3)	C9—C14	1.387 (3)
N1—N2	1.383 (3)	C9—C10	1.400 (3)
N2—C8	1.351 (3)	C10—C11	1.393 (4)
N2—H2	0.901 (10)	C10—C15	1.501 (4)
O1—C8	1.226 (3)	C11—C12	1.364 (4)
C1—C2	1.389 (3)	C11—H11	0.9300
C1—C6	1.393 (3)	C12—C13	1.371 (4)
C1—C7	1.458 (3)	C12—H12	0.9300
C2—C3	1.384 (3)	C13—C14	1.379 (3)
C3—C4	1.364 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.368 (3)	C15—H15A	0.9600
C5—C6	1.377 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300
C7—N1—N2	114.4 (2)	O1—C8—C9	122.6 (2)
C8—N2—N1	118.9 (2)	N2—C8—C9	114.1 (2)
C8—N2—H2	120.6 (18)	C14—C9—C10	120.0 (2)
N1—N2—H2	120.3 (18)	C14—C9—C8	119.5 (2)
C2—C1—C6	116.7 (2)	C10—C9—C8	120.5 (2)
C2—C1—C7	121.9 (2)	C11—C10—C9	116.9 (3)
C6—C1—C7	121.4 (3)	C11—C10—C15	119.9 (3)
C3—C2—C1	122.2 (2)	C9—C10—C15	123.2 (2)
C3—C2—Cl1	117.4 (2)	C12—C11—C10	122.7 (3)
C1—C2—Cl1	120.39 (19)	C12—C11—H11	118.7
C4—C3—C2	118.5 (3)	C10—C11—H11	118.7
C4—C3—H3	120.7	C11—C12—C13	120.0 (3)
C2—C3—H3	120.7	C11—C12—H12	120.0
C3—C4—C5	121.8 (2)	C13—C12—H12	120.0
C3—C4—Cl2	118.6 (2)	C12—C13—C14	119.2 (3)
C5—C4—Cl2	119.6 (2)	C12—C13—H13	120.4
C4—C5—C6	118.9 (2)	C14—C13—H13	120.4
C4—C5—H5	120.5	C13—C14—C9	121.1 (3)
C6—C5—H5	120.5	C13—C14—H14	119.4
C5—C6—C1	121.9 (3)	C9—C14—H14	119.4
C5—C6—H6	119.0	C10—C15—H15A	109.5
C1—C6—H6	119.0	C10—C15—H15B	109.5
N1—C7—C1	120.3 (2)	H15A—C15—H15B	109.5
N1—C7—H7	119.9	C10—C15—H15C	109.5
C1—C7—H7	119.9	H15A—C15—H15C	109.5
O1—C8—N2	123.2 (2)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	2.03 (1)	2.892 (3)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.90 (1)	2.03 (1)	2.892 (3)	159 (3)

Symmetry code: (i) .