4-Chloro-N'-(4-meth-oxy-benzyl-idene)benzohydrazide methanol monosolvate.

The title compound, C(15)H(13)ClN(2)O(2)·CH(4)O, consists of a 4-chloro-N'-(4-meth-oxy-benzyl-idene)benzohydrazide (CMB) mol-ecule and a methanol mol-ecule of crystallization. It was obtained by the condensation of 4-meth-oxy-benzaldehyde with 4-chloro-benzohydrazide. In the CMB mol-ecule, the dihedral angle between the two benzene rings is 50.1 (3)°. The methanol mol-ecule is linked to the CMB mol-ecule through O-H⋯O and O-H⋯N hydrogen bonds. In the crystal, CMB mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, involving the methanol mol-ecule, forming chains propagating along [010].

Related literature

For background to compounds obtained by the condensation of aldehydes with benzohydrazides, see: Qiu & Zhao (2008 ▶); Yathirajan et al. (2007 ▶); Salhin et al. (2007 ▶). For their biological properties, see: Bedia et al. (2006 ▶); Terzioglu & Gürsoy (2003 ▶); Küçükgüzel et al. (2003 ▶); Charkoudian et al. (2007 ▶). For similar compounds reported by our group, see: Huang (2009 ▶); Wu (2009 ▶). For other similar structures, see: Fun et al. (2008 ▶); Liu & Li (2004 ▶); Lei et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13ClN2O2·CH4O

M = 320.77

Monoclinic,

a = 10.914 (3) Å

b = 6.459 (2) Å

c = 11.358 (2) Å

β = 93.000 (3)°

V = 799.6 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.17 × 0.13 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.958, T max = 0.970

6424 measured reflections

1865 independent reflections

1030 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.123

S = 1.00

1865 reflections

201 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 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 datablocks global, I. DOI: 10.1107/S1600536810038857/su2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038857/su2215Isup2.hkl

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

C15H13ClN2O2·CH4O	F(000) = 336
Mr = 320.77	Dx = 1.332 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 640 reflections
a = 10.914 (3) Å	θ = 2.5–24.3°
b = 6.459 (2) Å	µ = 0.25 mm−1
c = 11.358 (2) Å	T = 298 K
β = 93.000 (3)°	Block, colorless
V = 799.6 (4) Å3	0.17 × 0.13 × 0.12 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	1865 independent reflections
Radiation source: fine-focus sealed tube	1030 reflections with I > 2σ(I)
graphite	Rint = 0.074
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.958, Tmax = 0.970	k = −7→8
6424 measured reflections	l = −14→14

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3
1865 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.19 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	0.58789 (14)	1.0709 (3)	1.25398 (13)	0.0754 (6)
O1	0.7358 (4)	0.4112 (6)	0.8320 (3)	0.0689 (13)
O2	1.0029 (3)	0.3682 (6)	0.1329 (3)	0.0573 (11)
N1	0.7495 (4)	0.7047 (7)	0.7275 (4)	0.0502 (12)
H1	0.7447	0.8376	0.7257	0.060*
N2	0.7810 (4)	0.5948 (7)	0.6283 (4)	0.0493 (12)
C1	0.6292 (5)	0.9354 (10)	1.1301 (5)	0.0505 (15)
C2	0.6174 (5)	1.0320 (9)	1.0215 (5)	0.0571 (16)
H2	0.5886	1.1673	1.0156	0.069*
C3	0.6487 (5)	0.9259 (9)	0.9215 (5)	0.0559 (15)
H3A	0.6402	0.9908	0.8484	0.067*
C4	0.6922 (4)	0.7256 (8)	0.9284 (5)	0.0395 (13)
C5	0.7063 (5)	0.6364 (9)	1.0389 (5)	0.0561 (16)
H5	0.7393	0.5039	1.0456	0.067*
C6	0.6732 (5)	0.7365 (10)	1.1399 (5)	0.0592 (17)
H6	0.6805	0.6708	1.2128	0.071*
C7	0.7264 (5)	0.5997 (10)	0.8265 (5)	0.0500 (14)
C8	0.8292 (5)	0.7001 (9)	0.5487 (5)	0.0482 (15)
H8	0.8390	0.8418	0.5605	0.058*
C9	0.8700 (4)	0.6108 (9)	0.4395 (4)	0.0424 (13)
C10	0.9473 (5)	0.7190 (8)	0.3688 (5)	0.0482 (14)
H10	0.9700	0.8532	0.3901	0.058*
C11	0.9914 (5)	0.6360 (9)	0.2693 (5)	0.0504 (15)
H11	1.0449	0.7116	0.2248	0.060*
C12	0.9561 (5)	0.4384 (9)	0.2346 (5)	0.0441 (14)
C13	0.8792 (5)	0.3255 (8)	0.3021 (4)	0.0448 (14)
H13	0.8558	0.1925	0.2791	0.054*
C14	0.8365 (5)	0.4103 (9)	0.4045 (5)	0.0492 (15)
H14	0.7852	0.3329	0.4503	0.059*
C15	0.9668 (6)	0.1704 (10)	0.0893 (5)	0.076 (2)
H15A	0.9827	0.0682	0.1496	0.115*
H15B	1.0125	0.1372	0.0218	0.115*
H15C	0.8807	0.1718	0.0670	0.115*
O3	0.7025 (4)	0.1217 (6)	0.6473 (4)	0.0689 (12)
H3	0.7236	0.2346	0.6745	0.103*
C16	0.5831 (6)	0.1364 (13)	0.5954 (5)	0.092 (2)
H16A	0.5772	0.2565	0.5456	0.139*
H16B	0.5254	0.1481	0.6560	0.139*
H16C	0.5651	0.0147	0.5491	0.139*

	U11	U22	U33	U12	U13	U23
Cl1	0.0776 (11)	0.0881 (14)	0.0620 (10)	−0.0048 (11)	0.0168 (8)	−0.0320 (10)
O1	0.111 (4)	0.035 (2)	0.063 (3)	0.008 (3)	0.018 (2)	−0.002 (2)
O2	0.074 (3)	0.051 (3)	0.049 (2)	0.004 (2)	0.024 (2)	−0.004 (2)
N1	0.069 (3)	0.030 (3)	0.052 (3)	0.004 (2)	0.014 (2)	−0.009 (2)
N2	0.064 (3)	0.035 (3)	0.050 (3)	0.003 (3)	0.011 (2)	−0.006 (3)
C1	0.041 (3)	0.065 (4)	0.046 (4)	−0.003 (3)	0.006 (3)	−0.023 (3)
C2	0.065 (4)	0.044 (4)	0.064 (4)	0.000 (3)	0.018 (3)	−0.009 (3)
C3	0.075 (4)	0.038 (3)	0.056 (4)	0.004 (3)	0.017 (3)	0.001 (3)
C4	0.044 (3)	0.034 (3)	0.040 (3)	0.001 (3)	0.004 (3)	−0.008 (3)
C5	0.053 (4)	0.048 (4)	0.068 (4)	0.014 (3)	0.004 (3)	0.003 (3)
C6	0.055 (4)	0.071 (5)	0.052 (4)	0.009 (4)	0.007 (3)	0.001 (4)
C7	0.054 (4)	0.042 (4)	0.054 (4)	0.004 (3)	0.008 (3)	0.001 (3)
C8	0.058 (4)	0.033 (3)	0.054 (4)	0.001 (3)	0.002 (3)	−0.007 (3)
C9	0.047 (3)	0.038 (3)	0.041 (3)	0.002 (3)	−0.001 (3)	−0.004 (3)
C10	0.056 (4)	0.034 (3)	0.054 (4)	−0.008 (3)	0.000 (3)	0.003 (3)
C11	0.059 (4)	0.045 (4)	0.048 (4)	−0.003 (3)	0.010 (3)	0.007 (3)
C12	0.046 (3)	0.045 (4)	0.041 (3)	0.006 (3)	−0.002 (3)	−0.001 (3)
C13	0.057 (4)	0.035 (3)	0.044 (3)	−0.008 (3)	0.010 (3)	−0.008 (3)
C14	0.060 (4)	0.037 (3)	0.051 (4)	−0.007 (3)	0.009 (3)	−0.001 (3)
C15	0.102 (6)	0.058 (5)	0.071 (5)	0.001 (4)	0.017 (4)	−0.022 (4)
O3	0.095 (3)	0.031 (3)	0.080 (3)	0.005 (2)	0.003 (2)	−0.006 (2)
C16	0.102 (6)	0.087 (6)	0.087 (5)	−0.001 (5)	−0.004 (4)	−0.013 (5)

Cl1—C1	1.736 (5)	C8—H8	0.9300
O1—C7	1.224 (7)	C9—C10	1.384 (7)
O2—C12	1.364 (6)	C9—C14	1.398 (8)
O2—C15	1.419 (7)	C10—C11	1.362 (7)
N1—C7	1.349 (6)	C10—H10	0.9300
N1—N2	1.389 (5)	C11—C12	1.385 (7)
N1—H1	0.8600	C11—H11	0.9300
N2—C8	1.268 (6)	C12—C13	1.375 (7)
C1—C6	1.374 (8)	C13—C14	1.389 (6)
C1—C2	1.383 (7)	C13—H13	0.9300
C2—C3	1.384 (7)	C14—H14	0.9300
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.379 (7)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.383 (7)	O3—C16	1.406 (6)
C4—C7	1.477 (7)	O3—H3	0.8200
C5—C6	1.381 (7)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C8—C9	1.458 (7)
C12—O2—C15	119.0 (4)	C10—C9—C8	121.1 (5)
C7—N1—N2	119.0 (4)	C14—C9—C8	121.4 (5)
C7—N1—H1	120.5	C11—C10—C9	122.4 (5)
N2—N1—H1	120.5	C11—C10—H10	118.8
C8—N2—N1	115.7 (5)	C9—C10—H10	118.8
C6—C1—C2	120.6 (5)	C10—C11—C12	119.6 (5)
C6—C1—Cl1	120.7 (5)	C10—C11—H11	120.2
C2—C1—Cl1	118.7 (5)	C12—C11—H11	120.2
C1—C2—C3	119.6 (6)	O2—C12—C13	124.2 (5)
C1—C2—H2	120.2	O2—C12—C11	115.9 (5)
C3—C2—H2	120.2	C13—C12—C11	119.9 (5)
C4—C3—C2	121.1 (6)	C12—C13—C14	120.0 (5)
C4—C3—H3A	119.4	C12—C13—H13	120.0
C2—C3—H3A	119.4	C14—C13—H13	120.0
C3—C4—C5	117.6 (5)	C13—C14—C9	120.6 (5)
C3—C4—C7	124.9 (5)	C13—C14—H14	119.7
C5—C4—C7	117.5 (5)	C9—C14—H14	119.7
C6—C5—C4	122.5 (5)	O2—C15—H15A	109.5
C6—C5—H5	118.7	O2—C15—H15B	109.5
C4—C5—H5	118.7	H15A—C15—H15B	109.5
C1—C6—C5	118.4 (6)	O2—C15—H15C	109.5
C1—C6—H6	120.8	H15A—C15—H15C	109.5
C5—C6—H6	120.8	H15B—C15—H15C	109.5
O1—C7—N1	121.6 (5)	C16—O3—H3	109.5
O1—C7—C4	122.1 (5)	O3—C16—H16A	109.5
N1—C7—C4	116.3 (5)	O3—C16—H16B	109.5
N2—C8—C9	123.5 (5)	H16A—C16—H16B	109.5
N2—C8—H8	118.3	O3—C16—H16C	109.5
C9—C8—H8	118.3	H16A—C16—H16C	109.5
C10—C9—C14	117.5 (5)	H16B—C16—H16C	109.5
C7—N1—N2—C8	−164.0 (5)	C5—C4—C7—N1	−159.7 (5)
C6—C1—C2—C3	0.9 (8)	N1—N2—C8—C9	178.9 (4)
Cl1—C1—C2—C3	−179.4 (4)	N2—C8—C9—C10	−164.4 (5)
C1—C2—C3—C4	−0.4 (9)	N2—C8—C9—C14	13.1 (8)
C2—C3—C4—C5	−1.5 (8)	C14—C9—C10—C11	−0.7 (8)
C2—C3—C4—C7	179.2 (5)	C8—C9—C10—C11	176.9 (5)
C3—C4—C5—C6	3.1 (8)	C9—C10—C11—C12	1.7 (8)
C7—C4—C5—C6	−177.6 (5)	C15—O2—C12—C13	3.0 (8)
C2—C1—C6—C5	0.6 (8)	C15—O2—C12—C11	−177.5 (5)
Cl1—C1—C6—C5	−179.2 (4)	C10—C11—C12—O2	179.0 (5)
C4—C5—C6—C1	−2.7 (9)	C10—C11—C12—C13	−1.5 (8)
N2—N1—C7—O1	2.0 (8)	O2—C12—C13—C14	179.9 (5)
N2—N1—C7—C4	−179.4 (4)	C11—C12—C13—C14	0.4 (8)
C3—C4—C7—O1	−161.9 (5)	C12—C13—C14—C9	0.6 (8)
C5—C4—C7—O1	18.8 (8)	C10—C9—C14—C13	−0.5 (7)
C3—C4—C7—N1	19.5 (8)	C8—C9—C14—C13	−178.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	2.47	3.184 (6)	146
O3—H3···O1	0.82	2.12	2.820 (6)	143
N1—H1···O3i	0.86	2.08	2.880 (6)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	2.47	3.184 (6)	146
O3—H3⋯O1	0.82	2.12	2.820 (6)	143
N1—H1⋯O3i	0.86	2.08	2.880 (6)	154

Symmetry code: (i) .