N'-(2-Chloro-benzyl-idene)-2-hydr-oxy-3-methyl-benzohydrazide.

In the title compound, C(15)H(13)ClN(2)O(2), the dihedral angle between the two benzene rings is 3.4 (5)° and the mol-ecule adopts an E configuration with respect to the C=N bond. There is an intra-molecular O-H⋯O hydrogen bond in the mol-ecule, which generates an S(6) loop. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming C(4) chains running along the a axis.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶); Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13ClN2O2

M = 288.72

Monoclinic,

a = 7.084 (2) Å

b = 27.010 (3) Å

c = 7.755 (2) Å

β = 111.229 (3)°

V = 1383.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.967, T max = 0.973

3856 measured reflections

1981 independent reflections

1145 reflections with I > 2σ(I)

R int = 0.151

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.220

S = 0.92

1981 reflections

183 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.45 e Å−3

Absolute structure: Flack (1983 ▶), 470 Friedel pairs

Flack parameter: 0.29 (17)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012110/hb5388sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012110/hb5388Isup2.hkl

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

C15H13ClN2O2	F(000) = 600
Mr = 288.72	Dx = 1.387 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 975 reflections
a = 7.084 (2) Å	θ = 2.6–24.5°
b = 27.010 (3) Å	µ = 0.28 mm−1
c = 7.755 (2) Å	T = 298 K
β = 111.229 (3)°	Block, colorless
V = 1383.1 (6) Å3	0.12 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	1981 independent reflections
Radiation source: fine-focus sealed tube	1145 reflections with I > 2σ(I)
graphite	Rint = 0.151
ω scans	θmax = 27.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −4→9
Tmin = 0.967, Tmax = 0.973	k = −34→34
3856 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.083	H-atom parameters constrained
wR(F2) = 0.220	w = 1/[σ2(Fo2) + (0.1271P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max = 0.001
1981 reflections	Δρmax = 0.39 e Å−3
183 parameters	Δρmin = −0.45 e Å−3
2 restraints	Absolute structure: Flack (1983), 470 Fridel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.29 (17)

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 > 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	0.3375 (3)	0.43050 (6)	0.8129 (3)	0.0785 (7)
N1	0.2710 (8)	0.24748 (18)	0.8198 (7)	0.0526 (14)
H1	0.3490	0.2572	0.9277	0.063*
N2	0.2275 (8)	0.2780 (2)	0.6677 (6)	0.0503 (13)
O1	0.0826 (8)	0.18614 (19)	0.6388 (6)	0.0704 (15)
O2	0.1832 (8)	0.09660 (18)	0.7787 (7)	0.0666 (14)
H2	0.1443	0.1174	0.6964	0.100*
C1	0.2311 (9)	0.1713 (2)	0.9627 (8)	0.0462 (15)
C2	0.2276 (10)	0.1188 (2)	0.9446 (8)	0.0505 (16)
C3	0.2680 (10)	0.0889 (3)	1.1021 (10)	0.0599 (19)
C4	0.3049 (11)	0.1111 (3)	1.2688 (9)	0.065 (2)
H4	0.3328	0.0912	1.3730	0.078*
C5	0.3026 (12)	0.1623 (3)	1.2901 (11)	0.067 (2)
H5	0.3253	0.1762	1.4055	0.081*
C6	0.2661 (9)	0.1919 (3)	1.1361 (8)	0.0550 (17)
H6	0.2648	0.2262	1.1484	0.066*
C7	0.1867 (9)	0.2013 (2)	0.7943 (8)	0.0489 (16)
C8	0.2946 (10)	0.3218 (3)	0.7035 (9)	0.0485 (15)
H8	0.3665	0.3312	0.8251	0.058*
C9	0.2591 (9)	0.3575 (2)	0.5540 (8)	0.0445 (14)
C10	0.2758 (10)	0.4085 (2)	0.5897 (9)	0.0548 (18)
C11	0.2424 (13)	0.4419 (3)	0.4451 (12)	0.070 (2)
H11	0.2509	0.4757	0.4689	0.084*
C12	0.1983 (14)	0.4256 (3)	0.2722 (13)	0.078 (2)
H12	0.1778	0.4485	0.1775	0.093*
C13	0.1823 (11)	0.3753 (3)	0.2297 (9)	0.066 (2)
H13	0.1523	0.3645	0.1087	0.079*
C14	0.2122 (10)	0.3417 (3)	0.3723 (9)	0.0555 (18)
H14	0.2008	0.3080	0.3462	0.067*
C15	0.2730 (15)	0.0336 (3)	1.0799 (14)	0.085 (3)
H15A	0.3750	0.0251	1.0306	0.127*
H15B	0.1433	0.0224	0.9969	0.127*
H15C	0.3037	0.0180	1.1982	0.127*

	U11	U22	U33	U12	U13	U23
Cl1	0.1018 (16)	0.0557 (10)	0.0756 (12)	−0.0051 (12)	0.0294 (10)	−0.0184 (10)
N1	0.063 (3)	0.044 (3)	0.035 (2)	−0.005 (3)	−0.001 (2)	0.005 (2)
N2	0.056 (3)	0.049 (3)	0.034 (2)	−0.002 (3)	0.002 (2)	0.002 (2)
O1	0.100 (4)	0.057 (3)	0.034 (2)	−0.024 (3)	0.001 (2)	−0.001 (2)
O2	0.087 (4)	0.049 (3)	0.058 (3)	−0.002 (3)	0.020 (3)	−0.005 (2)
C1	0.042 (3)	0.046 (3)	0.039 (3)	−0.001 (3)	0.001 (3)	0.001 (3)
C2	0.050 (4)	0.049 (3)	0.043 (3)	−0.003 (3)	0.005 (3)	0.006 (3)
C3	0.052 (4)	0.056 (4)	0.062 (5)	0.001 (3)	0.009 (3)	0.015 (3)
C4	0.063 (5)	0.075 (5)	0.050 (4)	−0.001 (4)	0.012 (4)	0.025 (4)
C5	0.066 (5)	0.089 (6)	0.043 (3)	−0.008 (4)	0.015 (3)	−0.003 (4)
C6	0.059 (4)	0.059 (4)	0.038 (3)	−0.007 (3)	0.007 (3)	0.001 (3)
C7	0.051 (4)	0.049 (3)	0.034 (3)	−0.005 (3)	0.001 (3)	−0.003 (3)
C8	0.048 (4)	0.049 (4)	0.039 (3)	−0.007 (3)	0.003 (2)	0.001 (3)
C9	0.046 (3)	0.043 (3)	0.041 (3)	0.002 (3)	0.011 (3)	0.003 (3)
C10	0.058 (4)	0.044 (3)	0.060 (4)	−0.003 (3)	0.018 (3)	−0.005 (3)
C11	0.078 (5)	0.047 (4)	0.082 (6)	0.009 (4)	0.024 (4)	0.012 (4)
C12	0.085 (6)	0.071 (5)	0.074 (5)	0.010 (5)	0.024 (4)	0.032 (5)
C13	0.066 (5)	0.082 (5)	0.038 (3)	0.001 (4)	0.006 (3)	0.012 (3)
C14	0.051 (4)	0.061 (4)	0.048 (4)	−0.004 (3)	0.011 (3)	0.008 (3)
C15	0.093 (6)	0.057 (4)	0.100 (7)	0.006 (5)	0.028 (5)	0.024 (5)

Cl1—C10	1.730 (7)	C5—H5	0.9300
N1—C7	1.365 (8)	C6—H6	0.9300
N1—N2	1.379 (7)	C8—C9	1.458 (9)
N1—H1	0.8600	C8—H8	0.9300
N2—C8	1.268 (8)	C9—C14	1.392 (10)
O1—C7	1.234 (7)	C9—C10	1.400 (8)
O2—C2	1.350 (8)	C10—C11	1.392 (10)
O2—H2	0.8200	C11—C12	1.336 (12)
C1—C6	1.392 (9)	C11—H11	0.9300
C1—C2	1.423 (8)	C12—C13	1.392 (12)
C1—C7	1.472 (9)	C12—H12	0.9300
C2—C3	1.405 (9)	C13—C14	1.387 (10)
C3—C4	1.362 (10)	C13—H13	0.9300
C3—C15	1.506 (12)	C14—H14	0.9300
C4—C5	1.394 (11)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.382 (10)	C15—H15C	0.9600
C7—N1—N2	118.1 (4)	N2—C8—H8	120.0
C7—N1—H1	121.0	C9—C8—H8	120.0
N2—N1—H1	121.0	C14—C9—C10	118.3 (6)
C8—N2—N1	114.9 (5)	C14—C9—C8	120.7 (6)
C2—O2—H2	109.5	C10—C9—C8	121.0 (6)
C6—C1—C2	119.0 (6)	C11—C10—C9	120.0 (6)
C6—C1—C7	122.8 (6)	C11—C10—Cl1	119.4 (5)
C2—C1—C7	118.1 (5)	C9—C10—Cl1	120.6 (5)
O2—C2—C3	118.4 (6)	C12—C11—C10	120.3 (7)
O2—C2—C1	121.8 (5)	C12—C11—H11	119.8
C3—C2—C1	119.8 (6)	C10—C11—H11	119.8
C4—C3—C2	118.7 (7)	C11—C12—C13	121.9 (7)
C4—C3—C15	122.7 (7)	C11—C12—H12	119.1
C2—C3—C15	118.5 (7)	C13—C12—H12	119.1
C3—C4—C5	122.9 (7)	C14—C13—C12	118.3 (7)
C3—C4—H4	118.6	C14—C13—H13	120.9
C5—C4—H4	118.6	C12—C13—H13	120.9
C6—C5—C4	118.6 (7)	C13—C14—C9	121.2 (7)
C6—C5—H5	120.7	C13—C14—H14	119.4
C4—C5—H5	120.7	C9—C14—H14	119.4
C5—C6—C1	121.0 (7)	C3—C15—H15A	109.5
C5—C6—H6	119.5	C3—C15—H15B	109.5
C1—C6—H6	119.5	H15A—C15—H15B	109.5
O1—C7—N1	121.4 (6)	C3—C15—H15C	109.5
O1—C7—C1	122.9 (6)	H15A—C15—H15C	109.5
N1—C7—C1	115.7 (5)	H15B—C15—H15C	109.5
N2—C8—C9	120.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.41	3.202 (7)	154
O2—H2···O1	0.82	1.92	2.641 (7)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.41	3.202 (7)	154
O2—H2⋯O1	0.82	1.92	2.641 (7)	146

Symmetry code: (i) .