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

In the title compound, C(15)H(13)ClN(2)O, the mol-ecule displays a trans conformation with respect to the C=N bond. The two aromatic rings form a dihedral angle of 12.0 (3)°. In the crystal, mol-ecules are connected via N-H⋯O hydrogen bonds into chains propagating along the c-axis direction.

Related literature

For the crystal structures of hydrazones, see: Wardell et al. (2006 ▶); Kummerle et al. (2009 ▶). For bond-length data, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C15H13ClN2O

M = 272.72

Monoclinic,

a = 11.0697 (14) Å

b = 13.4436 (16) Å

c = 9.1643 (11) Å

β = 96.576 (2)°

V = 1354.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.10 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T min = 0.973, T max = 0.981

11486 measured reflections

2096 independent reflections

1682 reflections with I > 2σ(I)

R int = 0.026

θmax = 23.9°

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.03

2096 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.18 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 datablock(s) global, I. DOI: 10.1107/S1600536812024099/hb6816sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024099/hb6816Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024099/hb6816Isup3.cml

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

C15H13ClN2O	F(000) = 568
Mr = 272.72	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5323 reflections
a = 11.0697 (14) Å	θ = 2.4–24.3°
b = 13.4436 (16) Å	µ = 0.28 mm−1
c = 9.1643 (11) Å	T = 298 K
β = 96.576 (2)°	Block, colorless
V = 1354.8 (3) Å3	0.10 × 0.10 × 0.07 mm
Z = 4

Bruker SMART CCD diffractometer	2096 independent reflections
Radiation source: fine-focus sealed tube	1682 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 23.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.973, Tmax = 0.981	k = −15→15
11486 measured reflections	l = −9→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.051P)2 + 0.4392P] where P = (Fo2 + 2Fc2)/3
2096 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.18 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	0.73671 (7)	−0.12300 (4)	0.12887 (7)	0.0804 (3)
N1	0.68758 (14)	0.16431 (11)	−0.06660 (16)	0.0437 (4)
N2	0.73084 (15)	0.24311 (11)	0.02057 (16)	0.0440 (4)
O1	0.76428 (13)	0.33102 (10)	−0.18063 (13)	0.0560 (4)
C1	0.62975 (16)	−0.00454 (13)	−0.0883 (2)	0.0444 (5)
C2	0.65016 (18)	−0.10128 (14)	−0.0383 (2)	0.0508 (5)
C3	0.6060 (2)	−0.18270 (15)	−0.1196 (2)	0.0611 (6)
H3	0.6209	−0.2467	−0.0835	0.073*
C4	0.5403 (2)	−0.16849 (17)	−0.2538 (3)	0.0673 (6)
H4	0.5098	−0.2229	−0.3088	0.081*
C5	0.5195 (2)	−0.07398 (17)	−0.3069 (2)	0.0655 (6)
H5	0.4752	−0.0645	−0.3984	0.079*
C6	0.56356 (18)	0.00679 (16)	−0.2258 (2)	0.0548 (5)
H6	0.5489	0.0704	−0.2636	0.066*
C7	0.67597 (17)	0.08183 (13)	−0.0024 (2)	0.0453 (5)
H7	0.6967	0.0764	0.0986	0.054*
C8	0.76952 (17)	0.32495 (13)	−0.04646 (19)	0.0415 (4)
C9	0.81732 (17)	0.40832 (12)	0.04982 (19)	0.0404 (4)
C10	0.86287 (18)	0.39728 (13)	0.1951 (2)	0.0455 (5)
H10	0.8641	0.3347	0.2385	0.055*
C11	0.90664 (18)	0.47857 (15)	0.2764 (2)	0.0534 (5)
H11	0.9381	0.4694	0.3740	0.064*
C12	0.90528 (18)	0.57268 (14)	0.2177 (2)	0.0527 (5)
C13	0.8605 (2)	0.58265 (16)	0.0728 (3)	0.0707 (7)
H13	0.8585	0.6454	0.0299	0.085*
C14	0.8183 (2)	0.50216 (15)	−0.0111 (2)	0.0661 (6)
H14	0.7903	0.5111	−0.1098	0.079*
C15	0.9510 (2)	0.66110 (18)	0.3086 (3)	0.0776 (7)
H15A	0.9073	0.6662	0.3930	0.116*
H15B	0.9387	0.7205	0.2507	0.116*
H15C	1.0362	0.6530	0.3402	0.116*
H2	0.740 (2)	0.2368 (18)	0.1184 (11)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1227 (6)	0.0485 (4)	0.0643 (4)	0.0043 (3)	−0.0136 (4)	0.0008 (3)
N1	0.0568 (10)	0.0352 (8)	0.0386 (9)	−0.0009 (7)	0.0025 (7)	−0.0062 (7)
N2	0.0665 (10)	0.0329 (8)	0.0319 (8)	−0.0025 (7)	0.0022 (8)	−0.0019 (7)
O1	0.0919 (11)	0.0446 (8)	0.0314 (7)	−0.0007 (7)	0.0065 (7)	0.0009 (6)
C1	0.0503 (11)	0.0411 (10)	0.0433 (11)	−0.0045 (8)	0.0118 (9)	−0.0052 (8)
C2	0.0595 (12)	0.0430 (11)	0.0510 (12)	−0.0032 (9)	0.0104 (10)	−0.0071 (9)
C3	0.0737 (14)	0.0397 (11)	0.0710 (15)	−0.0060 (10)	0.0132 (12)	−0.0104 (10)
C4	0.0755 (15)	0.0543 (14)	0.0714 (16)	−0.0171 (11)	0.0052 (13)	−0.0230 (12)
C5	0.0703 (15)	0.0673 (15)	0.0565 (13)	−0.0130 (11)	−0.0027 (11)	−0.0109 (11)
C6	0.0607 (12)	0.0499 (12)	0.0528 (12)	−0.0068 (10)	0.0028 (10)	−0.0039 (10)
C7	0.0591 (12)	0.0387 (10)	0.0380 (10)	−0.0013 (9)	0.0054 (9)	−0.0036 (8)
C8	0.0542 (11)	0.0357 (10)	0.0343 (10)	0.0069 (8)	0.0044 (8)	0.0016 (8)
C9	0.0508 (11)	0.0338 (9)	0.0373 (10)	0.0016 (8)	0.0074 (8)	0.0007 (7)
C10	0.0599 (12)	0.0358 (10)	0.0404 (11)	−0.0023 (8)	0.0033 (9)	0.0043 (8)
C11	0.0643 (13)	0.0512 (12)	0.0427 (11)	−0.0079 (10)	−0.0019 (9)	−0.0029 (9)
C12	0.0534 (12)	0.0444 (12)	0.0610 (13)	−0.0091 (9)	0.0099 (10)	−0.0072 (10)
C13	0.1038 (19)	0.0339 (11)	0.0721 (16)	−0.0111 (11)	0.0008 (14)	0.0086 (10)
C14	0.1066 (18)	0.0429 (12)	0.0456 (12)	−0.0066 (12)	−0.0057 (12)	0.0091 (10)
C15	0.0850 (17)	0.0563 (14)	0.0914 (19)	−0.0249 (12)	0.0092 (14)	−0.0196 (13)

Cl1—C2	1.736 (2)	C7—H7	0.9300
N1—C7	1.269 (2)	C8—C9	1.486 (2)
N1—N2	1.379 (2)	C9—C10	1.376 (3)
N2—C8	1.353 (2)	C9—C14	1.380 (3)
N2—H2	0.895 (9)	C10—C11	1.379 (3)
O1—C8	1.227 (2)	C10—H10	0.9300
C1—C2	1.389 (3)	C11—C12	1.374 (3)
C1—C6	1.391 (3)	C11—H11	0.9300
C1—C7	1.462 (2)	C12—C13	1.370 (3)
C2—C3	1.382 (3)	C12—C15	1.505 (3)
C3—C4	1.368 (3)	C13—C14	1.377 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.371 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.374 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300
C7—N1—N2	116.71 (15)	O1—C8—C9	121.18 (16)
C8—N2—N1	117.93 (14)	N2—C8—C9	116.96 (15)
C8—N2—H2	121.8 (16)	C10—C9—C14	118.10 (17)
N1—N2—H2	119.9 (16)	C10—C9—C8	123.99 (15)
C2—C1—C6	116.78 (17)	C14—C9—C8	117.90 (16)
C2—C1—C7	122.13 (17)	C9—C10—C11	120.29 (17)
C6—C1—C7	121.09 (17)	C9—C10—H10	119.9
C3—C2—C1	121.96 (19)	C11—C10—H10	119.9
C3—C2—Cl1	117.91 (16)	C12—C11—C10	122.04 (18)
C1—C2—Cl1	120.10 (14)	C12—C11—H11	119.0
C4—C3—C2	119.5 (2)	C10—C11—H11	119.0
C4—C3—H3	120.2	C13—C12—C11	117.12 (18)
C2—C3—H3	120.2	C13—C12—C15	121.4 (2)
C3—C4—C5	119.95 (19)	C11—C12—C15	121.5 (2)
C3—C4—H4	120.0	C12—C13—C14	121.75 (19)
C5—C4—H4	120.0	C12—C13—H13	119.1
C4—C5—C6	120.4 (2)	C14—C13—H13	119.1
C4—C5—H5	119.8	C13—C14—C9	120.66 (19)
C6—C5—H5	119.8	C13—C14—H14	119.7
C5—C6—C1	121.4 (2)	C9—C14—H14	119.7
C5—C6—H6	119.3	C12—C15—H15A	109.5
C1—C6—H6	119.3	C12—C15—H15B	109.5
N1—C7—C1	119.45 (16)	H15A—C15—H15B	109.5
N1—C7—H7	120.3	C12—C15—H15C	109.5
C1—C7—H7	120.3	H15A—C15—H15C	109.5
O1—C8—N2	121.86 (16)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	2.05 (1)	2.8976 (19)	159 (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)	2.05 (1)	2.8976 (19)	159 (2)

Symmetry code: (i) .