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

The title hydrazone compound, C(15)H(13)ClN(2)O, adopts an E configuration about the C=N double bond. The dihedral angle between the two benzene rings is 13.1 (2)°. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds, forming chains parallel to [101].

Related literature

For the biological properties of hydrazone compounds, see: Ajani et al. (2010 ▶); Angelusiu et al. (2010 ▶); Zhang et al. (2010 ▶); Horiuchi et al. (2009 ▶). For the crystal structures of similar hydrazone comounds, see: Ban (2010 ▶); Hussain et al. (2010 ▶); Shalash et al. (2010 ▶); Khaledi et al. (2009 ▶). For the crystal structure of the 2-fluorobenzohydrazide analoque, reported on recently by the author, see: Zhang (2011 ▶).

Experimental

Crystal data

C15H13ClN2O

M = 272.72

Monoclinic,

a = 7.4305 (17) Å

b = 25.596 (2) Å

c = 7.7926 (18) Å

β = 113.505 (2)°

V = 1359.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.947, T max = 0.947

7513 measured reflections

2516 independent reflections

1870 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.141

S = 1.08

2516 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536812000463/qm2047sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000463/qm2047Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000463/qm2047Isup3.cml

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

C15H13ClN2O	F(000) = 568
Mr = 272.72	Dx = 1.333 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4305 (17) Å	Cell parameters from 2213 reflections
b = 25.596 (2) Å	θ = 2.7–24.5°
c = 7.7926 (18) Å	µ = 0.27 mm−1
β = 113.505 (2)°	T = 298 K
V = 1359.1 (5) Å3	Block, colorless
Z = 4	0.20 × 0.20 × 0.20 mm

Bruker APEXII CCD area-detector diffractometer	2516 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.947, Tmax = 0.947	k = −25→31
7513 measured reflections	l = −9→9

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0445P)2 + 1.1147P] where P = (Fo2 + 2Fc2)/3
2516 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.33 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	0.29514 (17)	0.04920 (3)	0.54672 (14)	0.0790 (4)
N1	0.1795 (3)	0.21108 (8)	0.4023 (3)	0.0380 (5)
N2	0.2213 (3)	0.24341 (8)	0.5565 (3)	0.0388 (6)
O1	0.0050 (3)	0.30528 (7)	0.3860 (2)	0.0468 (5)
C1	0.2276 (4)	0.12767 (10)	0.2918 (4)	0.0374 (6)
C2	0.2488 (4)	0.07402 (11)	0.3250 (4)	0.0465 (7)
C3	0.2323 (5)	0.03896 (12)	0.1830 (5)	0.0581 (9)
H3	0.2448	0.0033	0.2069	0.070*
C4	0.1976 (5)	0.05753 (14)	0.0072 (5)	0.0611 (9)
H4	0.1865	0.0343	−0.0882	0.073*
C5	0.1791 (5)	0.11049 (13)	−0.0288 (4)	0.0546 (8)
H5	0.1573	0.1229	−0.1476	0.066*
C6	0.1931 (4)	0.14482 (11)	0.1120 (4)	0.0442 (7)
H6	0.1792	0.1804	0.0863	0.053*
C7	0.2488 (4)	0.16495 (10)	0.4419 (4)	0.0386 (6)
H7	0.3131	0.1549	0.5664	0.046*
C8	0.1263 (4)	0.28972 (10)	0.5363 (3)	0.0331 (6)
C9	0.1778 (4)	0.31909 (10)	0.7153 (4)	0.0349 (6)
C10	0.2087 (4)	0.37314 (11)	0.7235 (4)	0.0432 (7)
C11	0.2488 (5)	0.39768 (14)	0.8949 (5)	0.0634 (10)
H11	0.2718	0.4335	0.9046	0.076*
C12	0.2553 (5)	0.37064 (17)	1.0496 (5)	0.0728 (11)
H12	0.2811	0.3883	1.1612	0.087*
C13	0.2242 (5)	0.31800 (17)	1.0403 (4)	0.0663 (10)
H13	0.2282	0.2997	1.1450	0.080*
C14	0.1869 (4)	0.29217 (12)	0.8746 (4)	0.0475 (7)
H14	0.1673	0.2562	0.8686	0.057*
C15	0.2020 (5)	0.40465 (12)	0.5579 (5)	0.0598 (9)
H15A	0.2780	0.3874	0.4998	0.090*
H15B	0.2554	0.4388	0.5990	0.090*
H15C	0.0685	0.4078	0.4693	0.090*
H2	0.312 (4)	0.2342 (13)	0.669 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1180 (9)	0.0447 (5)	0.0724 (6)	0.0103 (5)	0.0360 (6)	0.0145 (4)
N1	0.0397 (13)	0.0355 (12)	0.0320 (11)	0.0014 (10)	0.0069 (10)	−0.0057 (9)
N2	0.0427 (14)	0.0341 (12)	0.0288 (11)	0.0062 (10)	0.0031 (10)	−0.0042 (9)
O1	0.0516 (12)	0.0383 (10)	0.0342 (10)	0.0068 (9)	−0.0002 (9)	−0.0008 (8)
C1	0.0312 (14)	0.0343 (14)	0.0432 (15)	−0.0029 (11)	0.0111 (12)	−0.0065 (12)
C2	0.0450 (18)	0.0389 (16)	0.0532 (18)	0.0018 (13)	0.0172 (14)	−0.0017 (13)
C3	0.058 (2)	0.0368 (17)	0.082 (2)	−0.0037 (14)	0.0298 (19)	−0.0161 (16)
C4	0.060 (2)	0.061 (2)	0.066 (2)	−0.0093 (17)	0.0283 (18)	−0.0288 (18)
C5	0.0511 (19)	0.070 (2)	0.0457 (17)	−0.0116 (16)	0.0223 (15)	−0.0140 (15)
C6	0.0418 (16)	0.0439 (16)	0.0436 (16)	−0.0045 (13)	0.0134 (13)	−0.0057 (13)
C7	0.0382 (16)	0.0374 (15)	0.0344 (14)	0.0021 (12)	0.0084 (12)	0.0002 (12)
C8	0.0316 (14)	0.0319 (13)	0.0313 (13)	−0.0028 (11)	0.0078 (11)	0.0004 (11)
C9	0.0266 (14)	0.0389 (15)	0.0357 (14)	0.0043 (11)	0.0087 (11)	−0.0038 (11)
C10	0.0307 (15)	0.0389 (15)	0.0531 (17)	0.0001 (12)	0.0096 (13)	−0.0090 (13)
C11	0.050 (2)	0.054 (2)	0.074 (2)	0.0003 (15)	0.0113 (18)	−0.0291 (18)
C12	0.062 (2)	0.097 (3)	0.0458 (19)	0.013 (2)	0.0072 (17)	−0.033 (2)
C13	0.057 (2)	0.103 (3)	0.0362 (17)	0.022 (2)	0.0159 (15)	−0.0005 (18)
C14	0.0462 (18)	0.0549 (18)	0.0384 (15)	0.0074 (14)	0.0137 (13)	0.0003 (13)
C15	0.054 (2)	0.0391 (17)	0.085 (2)	−0.0032 (15)	0.0269 (18)	0.0055 (16)

Cl1—C2	1.742 (3)	C7—H7	0.9300
N1—C7	1.276 (3)	C8—C9	1.494 (3)
N1—N2	1.388 (3)	C9—C14	1.397 (4)
N2—C8	1.356 (3)	C9—C10	1.400 (4)
N2—H2	0.899 (10)	C10—C11	1.396 (4)
O1—C8	1.225 (3)	C10—C15	1.505 (4)
C1—C6	1.391 (4)	C11—C12	1.374 (5)
C1—C2	1.395 (4)	C11—H11	0.9300
C1—C7	1.468 (4)	C12—C13	1.364 (5)
C2—C3	1.392 (4)	C12—H12	0.9300
C3—C4	1.374 (5)	C13—C14	1.377 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.380 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.377 (4)	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	123.1 (2)
C8—N2—N1	119.6 (2)	N2—C8—C9	113.8 (2)
C8—N2—H2	120 (2)	C14—C9—C10	119.9 (3)
N1—N2—H2	121 (2)	C14—C9—C8	119.0 (2)
C6—C1—C2	117.3 (2)	C10—C9—C8	121.0 (2)
C6—C1—C7	121.0 (2)	C11—C10—C9	117.2 (3)
C2—C1—C7	121.6 (2)	C11—C10—C15	120.0 (3)
C3—C2—C1	121.3 (3)	C9—C10—C15	122.8 (3)
C3—C2—Cl1	118.3 (2)	C12—C11—C10	122.1 (3)
C1—C2—Cl1	120.4 (2)	C12—C11—H11	118.9
C4—C3—C2	119.5 (3)	C10—C11—H11	118.9
C4—C3—H3	120.3	C13—C12—C11	120.3 (3)
C2—C3—H3	120.3	C13—C12—H12	119.8
C3—C4—C5	120.4 (3)	C11—C12—H12	119.8
C3—C4—H4	119.8	C12—C13—C14	119.4 (3)
C5—C4—H4	119.8	C12—C13—H13	120.3
C6—C5—C4	119.7 (3)	C14—C13—H13	120.3
C6—C5—H5	120.2	C13—C14—C9	121.1 (3)
C4—C5—H5	120.2	C13—C14—H14	119.4
C5—C6—C1	121.7 (3)	C9—C14—H14	119.4
C5—C6—H6	119.1	C10—C15—H15A	109.5
C1—C6—H6	119.1	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	123.1 (2)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	2.00 (1)	2.876 (3)	164 (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)	2.00 (1)	2.876 (3)	164 (3)

Symmetry code: (i) .