N'-(2,4-Dichloro-benzyl-idene)-4-methoxy-benzohydrazide methanol solvate.

In the title compound, C(15)H(12)Cl(2)N(2)O(2)·CH(3)OH, the hydrazone mol-ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.6 (2)°. In the crystal structure, the hydrazone and methanol mol-ecules are linked into a chain propagating along the a axis via N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the biological properties of hydrazone compounds, see: Küçükgüzel et al. (2003 ▶); Charkoudian et al. (2007 ▶). For the crystal structures of hydrazone compounds, see: Fun et al. (2008 ▶); Lo & Ng (2009 ▶); Ren (2009 ▶); Zhang (2009 ▶). For related structures, see: Wu (2009 ▶); Peng & Hou (2008 ▶); Mohd Lair et al. (2009 ▶).

Experimental

Crystal data

C15H12Cl2N2O2·CH4O

M = 355.21

Triclinic,

a = 6.7401 (11) Å

b = 8.9583 (14) Å

c = 14.567 (2) Å

α = 75.085 (2)°

β = 81.570 (2)°

γ = 83.445 (2)°

V = 838.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 298 K

0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.924, T max = 0.931

4896 measured reflections

3557 independent reflections

2461 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.128

S = 1.03

3557 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.31 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 datablocks global, I. DOI: 10.1107/S1600536809022624/ci2826sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022624/ci2826Isup2.hkl

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

C15H12Cl2N2O2·CH4O	Z = 2
Mr = 355.21	F(000) = 368
Triclinic, P1	Dx = 1.408 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7401 (11) Å	Cell parameters from 1307 reflections
b = 8.9583 (14) Å	θ = 2.3–26.7°
c = 14.567 (2) Å	µ = 0.40 mm−1
α = 75.085 (2)°	T = 298 K
β = 81.570 (2)°	Block, colourless
γ = 83.445 (2)°	0.20 × 0.18 × 0.18 mm
V = 838.1 (2) Å3

Bruker SMART CCD area-detector diffractometer	3557 independent reflections
Radiation source: fine-focus sealed tube	2461 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.924, Tmax = 0.931	k = −11→11
4896 measured reflections	l = −18→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.048P)2 + 0.3404P] where P = (Fo2 + 2Fc2)/3
3557 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.31 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	0.24871 (10)	0.73959 (10)	1.31319 (5)	0.0692 (2)
Cl2	0.81448 (12)	0.99939 (9)	1.42996 (5)	0.0719 (3)
N1	0.6168 (3)	0.8075 (2)	1.04117 (13)	0.0442 (5)
N2	0.5388 (3)	0.7708 (2)	0.96816 (13)	0.0451 (5)
O1	0.8442 (2)	0.7876 (2)	0.88034 (12)	0.0582 (5)
O2	0.4029 (3)	0.5972 (2)	0.58129 (13)	0.0661 (5)
O3	0.1098 (3)	0.7492 (2)	0.01521 (13)	0.0613 (5)
H3	0.0183	0.7737	−0.0185	0.092*
C1	0.5714 (3)	0.8617 (3)	1.19309 (16)	0.0415 (5)
C2	0.4710 (3)	0.8331 (3)	1.28613 (17)	0.0451 (6)
C3	0.5433 (4)	0.8734 (3)	1.35947 (17)	0.0502 (6)
H3A	0.4748	0.8523	1.4210	0.060*
C4	0.7199 (4)	0.9456 (3)	1.33905 (17)	0.0501 (6)
C5	0.8244 (4)	0.9770 (3)	1.24829 (17)	0.0506 (6)
H5	0.9432	1.0262	1.2357	0.061*
C6	0.7498 (4)	0.9343 (3)	1.17690 (17)	0.0469 (6)
H6	0.8205	0.9544	1.1158	0.056*
C7	0.4950 (4)	0.8199 (3)	1.11445 (16)	0.0462 (6)
H7	0.3601	0.8029	1.1183	0.055*
C8	0.6669 (3)	0.7618 (3)	0.88846 (16)	0.0416 (5)
C9	0.5841 (3)	0.7173 (3)	0.81095 (15)	0.0411 (5)
C10	0.6995 (4)	0.7383 (3)	0.72207 (17)	0.0490 (6)
H10	0.8226	0.7809	0.7130	0.059*
C11	0.6354 (4)	0.6974 (3)	0.64766 (17)	0.0553 (7)
H11	0.7148	0.7129	0.5887	0.066*
C12	0.4530 (4)	0.6333 (3)	0.65966 (17)	0.0487 (6)
C13	0.3364 (4)	0.6112 (3)	0.74703 (18)	0.0557 (7)
H13	0.2135	0.5685	0.7559	0.067*
C14	0.4030 (4)	0.6528 (3)	0.82198 (17)	0.0542 (7)
H14	0.3238	0.6370	0.8810	0.065*
C15	0.2166 (5)	0.5339 (4)	0.5880 (2)	0.0752 (9)
H15A	0.2099	0.4415	0.6391	0.113*
H15B	0.2050	0.5092	0.5288	0.113*
H15C	0.1084	0.6081	0.6008	0.113*
C16	0.0604 (5)	0.6214 (3)	0.0907 (2)	0.0715 (8)
H16A	0.1791	0.5753	0.1196	0.107*
H16B	0.0061	0.5466	0.0666	0.107*
H16C	−0.0377	0.6547	0.1376	0.107*
H2	0.4070 (17)	0.761 (3)	0.973 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0488 (4)	0.1016 (6)	0.0583 (4)	−0.0229 (4)	0.0003 (3)	−0.0181 (4)
Cl2	0.0865 (5)	0.0888 (6)	0.0534 (4)	−0.0131 (4)	−0.0237 (4)	−0.0297 (4)
N1	0.0427 (11)	0.0564 (12)	0.0384 (10)	−0.0082 (9)	−0.0097 (8)	−0.0159 (9)
N2	0.0362 (10)	0.0655 (13)	0.0396 (10)	−0.0100 (10)	−0.0066 (8)	−0.0202 (9)
O1	0.0410 (10)	0.0925 (14)	0.0470 (10)	−0.0223 (9)	−0.0023 (7)	−0.0221 (9)
O2	0.0677 (12)	0.0936 (15)	0.0495 (11)	−0.0154 (11)	−0.0066 (9)	−0.0365 (10)
O3	0.0389 (10)	0.0899 (14)	0.0539 (11)	−0.0146 (9)	−0.0084 (8)	−0.0097 (10)
C1	0.0419 (13)	0.0438 (13)	0.0402 (12)	−0.0003 (10)	−0.0089 (10)	−0.0120 (10)
C2	0.0386 (12)	0.0523 (15)	0.0439 (13)	−0.0012 (11)	−0.0064 (10)	−0.0114 (11)
C3	0.0509 (15)	0.0626 (16)	0.0381 (13)	−0.0006 (12)	−0.0054 (10)	−0.0158 (11)
C4	0.0601 (16)	0.0531 (15)	0.0432 (13)	0.0014 (12)	−0.0188 (11)	−0.0183 (11)
C5	0.0531 (15)	0.0544 (15)	0.0494 (14)	−0.0124 (12)	−0.0117 (11)	−0.0152 (12)
C6	0.0495 (14)	0.0539 (15)	0.0386 (12)	−0.0110 (11)	−0.0029 (10)	−0.0121 (11)
C7	0.0399 (13)	0.0586 (15)	0.0442 (13)	−0.0076 (11)	−0.0088 (10)	−0.0164 (11)
C8	0.0399 (13)	0.0474 (14)	0.0384 (12)	−0.0083 (10)	−0.0066 (10)	−0.0089 (10)
C9	0.0392 (12)	0.0472 (13)	0.0384 (12)	−0.0056 (10)	−0.0057 (9)	−0.0116 (10)
C10	0.0406 (13)	0.0641 (16)	0.0443 (13)	−0.0132 (11)	−0.0016 (10)	−0.0151 (12)
C11	0.0531 (15)	0.0764 (19)	0.0391 (13)	−0.0106 (13)	0.0034 (11)	−0.0216 (13)
C12	0.0527 (15)	0.0576 (15)	0.0411 (13)	−0.0039 (12)	−0.0089 (11)	−0.0198 (11)
C13	0.0486 (15)	0.0778 (19)	0.0495 (14)	−0.0240 (13)	−0.0027 (11)	−0.0251 (13)
C14	0.0519 (15)	0.0768 (18)	0.0394 (13)	−0.0224 (13)	0.0029 (11)	−0.0215 (12)
C15	0.071 (2)	0.102 (2)	0.0701 (19)	−0.0163 (17)	−0.0211 (16)	−0.0415 (18)
C16	0.0693 (19)	0.0626 (19)	0.084 (2)	−0.0067 (15)	−0.0218 (16)	−0.0125 (16)

Cl1—C2	1.745 (2)	C6—H6	0.93
Cl2—C4	1.743 (2)	C7—H7	0.93
N1—C7	1.268 (3)	C8—C9	1.487 (3)
N1—N2	1.378 (2)	C9—C14	1.380 (3)
N2—C8	1.356 (3)	C9—C10	1.389 (3)
N2—H2	0.893 (10)	C10—C11	1.369 (3)
O1—C8	1.226 (3)	C10—H10	0.93
O2—C12	1.360 (3)	C11—C12	1.385 (3)
O2—C15	1.417 (3)	C11—H11	0.93
O3—C16	1.401 (3)	C12—C13	1.374 (3)
O3—H3	0.82	C13—C14	1.387 (3)
C1—C6	1.392 (3)	C13—H13	0.93
C1—C2	1.397 (3)	C14—H14	0.93
C1—C7	1.468 (3)	C15—H15A	0.96
C2—C3	1.378 (3)	C15—H15B	0.96
C3—C4	1.377 (4)	C15—H15C	0.96
C3—H3A	0.93	C16—H16A	0.96
C4—C5	1.380 (3)	C16—H16B	0.96
C5—C6	1.373 (3)	C16—H16C	0.96
C5—H5	0.93
C7—N1—N2	116.93 (19)	C14—C9—C10	117.8 (2)
C8—N2—N1	117.23 (18)	C14—C9—C8	124.5 (2)
C8—N2—H2	123.2 (19)	C10—C9—C8	117.7 (2)
N1—N2—H2	119.4 (19)	C11—C10—C9	121.2 (2)
C12—O2—C15	118.8 (2)	C11—C10—H10	119.4
C16—O3—H3	109.5	C9—C10—H10	119.4
C6—C1—C2	116.9 (2)	C10—C11—C12	120.4 (2)
C6—C1—C7	120.4 (2)	C10—C11—H11	119.8
C2—C1—C7	122.7 (2)	C12—C11—H11	119.8
C3—C2—C1	122.3 (2)	O2—C12—C13	124.8 (2)
C3—C2—Cl1	117.74 (19)	O2—C12—C11	115.8 (2)
C1—C2—Cl1	119.93 (17)	C13—C12—C11	119.4 (2)
C4—C3—C2	118.2 (2)	C12—C13—C14	119.7 (2)
C4—C3—H3A	120.9	C12—C13—H13	120.2
C2—C3—H3A	120.9	C14—C13—H13	120.2
C3—C4—C5	121.8 (2)	C9—C14—C13	121.5 (2)
C3—C4—Cl2	119.34 (19)	C9—C14—H14	119.2
C5—C4—Cl2	118.9 (2)	C13—C14—H14	119.2
C6—C5—C4	118.7 (2)	O2—C15—H15A	109.5
C6—C5—H5	120.6	O2—C15—H15B	109.5
C4—C5—H5	120.6	H15A—C15—H15B	109.5
C5—C6—C1	122.1 (2)	O2—C15—H15C	109.5
C5—C6—H6	119.0	H15A—C15—H15C	109.5
C1—C6—H6	119.0	H15B—C15—H15C	109.5
N1—C7—C1	118.6 (2)	O3—C16—H16A	109.5
N1—C7—H7	120.7	O3—C16—H16B	109.5
C1—C7—H7	120.7	H16A—C16—H16B	109.5
O1—C8—N2	121.9 (2)	O3—C16—H16C	109.5
O1—C8—C9	120.9 (2)	H16A—C16—H16C	109.5
N2—C8—C9	117.20 (19)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.89 (1)	2.01 (1)	2.889 (3)	167 (3)
O3—H3···O1ii	0.82	1.99	2.780 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.893 (10)	2.013 (12)	2.889 (3)	167 (3)
O3—H3⋯O1ii	0.82	1.99	2.780 (2)	163

Symmetry codes: (i) ; (ii) .