N'-(3,5-Dichloro-2-hydroxy-benzyl-idene)-3-methoxy-benzohydrazide methanol solvate.

In the title compound, C(15)H(12)Cl(2)N(2)O(3)·CH(3)OH, the Schiff base mol-ecule is nearly planar, with a dihedral angle of 4.5 (2)° between the two benzene rings. An intra-molecular O-H⋯N hydrogen bond is observed. The methanol solvent mol-ecule is linked to the Schiff base mol-ecule through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff base compounds, see: Herrick et al. (2008 ▶); Suresh et al. (2007 ▶); Liu et al. (2007 ▶). For the background on biological activities, see: Bhandari et al. (2008 ▶); Sinha et al. (2008 ▶); Sun et al. (2008 ▶). For related structures, see: Wang et al. (2008 ▶); Tang (2008a ▶,b ▶); Yang & Zheng (2007 ▶).

Experimental

Crystal data

C15H12Cl2N2O3·CH4O

M = 371.21

Triclinic,

a = 7.742 (3) Å

b = 9.070 (3) Å

c = 12.296 (4) Å

α = 92.422 (5)°

β = 98.948 (5)°

γ = 96.954 (5)°

V = 845.0 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 298 (2) K

0.27 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.898, T max = 0.923

6888 measured reflections

3452 independent reflections

2253 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.131

S = 1.04

3452 reflections

224 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801235X/ci2593sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801235X/ci2593Isup2.hkl

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

C15H12Cl2N2O3·CH4O	Z = 2
Mr = 371.21	F000 = 384
Triclinic, P1	Dx = 1.459 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.742 (3) Å	Cell parameters from 1304 reflections
b = 9.070 (3) Å	θ = 2.4–24.5º
c = 12.296 (4) Å	µ = 0.41 mm−1
α = 92.422 (5)º	T = 298 (2) K
β = 98.948 (5)º	Block, yellow
γ = 96.954 (5)º	0.27 × 0.23 × 0.20 mm
V = 845.0 (5) Å3

Bruker SMART CCD area-detector diffractometer	3452 independent reflections
Radiation source: fine-focus sealed tube	2253 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 298(2) K	θmax = 26.5º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.898, Tmax = 0.923	k = −11→11
6888 measured reflections	l = −15→15

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0565P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3452 reflections	Δρmax = 0.27 e Å−3
224 parameters	Δρmin = −0.24 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.29231 (9)	−0.03639 (9)	0.10217 (6)	0.0659 (3)
Cl2	−0.37695 (9)	−0.28076 (8)	0.09465 (6)	0.0636 (3)
O1	0.2383 (2)	0.14041 (19)	0.29003 (15)	0.0532 (5)
H1	0.2219	0.1852	0.3461	0.080*
O2	0.3328 (2)	0.3979 (2)	0.51936 (17)	0.0729 (6)
O3	−0.0405 (3)	0.5968 (2)	0.88407 (15)	0.0659 (6)
O4	0.3034 (2)	0.6965 (2)	0.42945 (18)	0.0677 (6)
H4	0.3679	0.6328	0.4458	0.102*
N1	0.0576 (3)	0.2173 (2)	0.43529 (16)	0.0432 (5)
N2	0.0515 (3)	0.3093 (2)	0.52560 (17)	0.0455 (5)
C1	−0.0641 (3)	0.0367 (3)	0.2932 (2)	0.0408 (6)
C2	0.0927 (3)	0.0466 (3)	0.2486 (2)	0.0406 (6)
C3	0.0983 (3)	−0.0464 (3)	0.1565 (2)	0.0432 (6)
C4	−0.0443 (3)	−0.1470 (3)	0.1091 (2)	0.0474 (6)
H4A	−0.0375	−0.2083	0.0477	0.057*
C5	−0.1966 (3)	−0.1549 (3)	0.1541 (2)	0.0448 (6)
C6	−0.2080 (3)	−0.0639 (3)	0.2446 (2)	0.0460 (6)
H6	−0.3127	−0.0699	0.2733	0.055*
C7	−0.0786 (3)	0.1315 (3)	0.3889 (2)	0.0483 (7)
H7	−0.1848	0.1295	0.4156	0.058*
C8	0.2044 (3)	0.3995 (3)	0.5653 (2)	0.0438 (6)
C9	0.2074 (3)	0.4983 (3)	0.66579 (19)	0.0419 (6)
C10	0.0683 (3)	0.4953 (3)	0.7255 (2)	0.0422 (6)
H10	−0.0351	0.4307	0.7029	0.051*
C11	0.0864 (3)	0.5898 (3)	0.8188 (2)	0.0469 (6)
C12	0.2406 (4)	0.6849 (3)	0.8525 (2)	0.0557 (7)
H12	0.2523	0.7472	0.9159	0.067*
C13	0.3750 (4)	0.6877 (3)	0.7933 (2)	0.0596 (8)
H13	0.4778	0.7530	0.8161	0.072*
C14	0.3607 (3)	0.5946 (3)	0.6997 (2)	0.0505 (7)
H14	0.4535	0.5966	0.6598	0.061*
C15	−0.2031 (4)	0.5035 (4)	0.8545 (3)	0.0710 (9)
H15A	−0.2575	0.5241	0.7821	0.107*
H15B	−0.2796	0.5218	0.9066	0.107*
H15C	−0.1824	0.4012	0.8547	0.107*
C16	0.3991 (5)	0.8175 (4)	0.3948 (4)	0.1132 (15)
H16A	0.3265	0.8956	0.3822	0.170*
H16B	0.4388	0.7899	0.3274	0.170*
H16C	0.4992	0.8515	0.4503	0.170*
H2	−0.052 (2)	0.307 (3)	0.551 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0460 (4)	0.0854 (6)	0.0652 (5)	−0.0006 (4)	0.0214 (3)	−0.0269 (4)
Cl2	0.0477 (4)	0.0620 (5)	0.0732 (5)	−0.0078 (3)	0.0037 (3)	−0.0223 (4)
O1	0.0428 (10)	0.0569 (11)	0.0563 (12)	−0.0079 (9)	0.0142 (8)	−0.0200 (9)
O2	0.0505 (12)	0.0888 (15)	0.0777 (15)	−0.0132 (11)	0.0315 (11)	−0.0309 (12)
O3	0.0605 (12)	0.0825 (14)	0.0529 (12)	−0.0024 (11)	0.0200 (10)	−0.0229 (10)
O4	0.0470 (12)	0.0815 (15)	0.0784 (15)	0.0085 (10)	0.0202 (11)	0.0104 (12)
N1	0.0435 (12)	0.0456 (12)	0.0397 (12)	0.0026 (10)	0.0100 (9)	−0.0096 (10)
N2	0.0402 (12)	0.0526 (13)	0.0425 (12)	0.0005 (10)	0.0118 (10)	−0.0158 (10)
C1	0.0434 (14)	0.0383 (13)	0.0404 (14)	0.0037 (11)	0.0092 (11)	−0.0040 (11)
C2	0.0353 (13)	0.0410 (13)	0.0438 (15)	0.0014 (11)	0.0064 (11)	−0.0044 (11)
C3	0.0396 (14)	0.0501 (15)	0.0410 (14)	0.0070 (11)	0.0121 (11)	−0.0071 (12)
C4	0.0487 (15)	0.0480 (15)	0.0437 (15)	0.0070 (12)	0.0053 (12)	−0.0125 (12)
C5	0.0385 (14)	0.0426 (14)	0.0492 (16)	−0.0004 (11)	0.0013 (11)	−0.0053 (12)
C6	0.0401 (14)	0.0469 (15)	0.0502 (16)	0.0013 (11)	0.0104 (12)	−0.0080 (12)
C7	0.0466 (15)	0.0508 (15)	0.0485 (16)	0.0016 (13)	0.0175 (13)	−0.0084 (13)
C8	0.0391 (14)	0.0456 (15)	0.0461 (15)	0.0019 (12)	0.0098 (12)	−0.0052 (12)
C9	0.0404 (14)	0.0446 (14)	0.0388 (14)	0.0048 (11)	0.0030 (11)	−0.0046 (11)
C10	0.0357 (13)	0.0455 (14)	0.0418 (14)	−0.0018 (11)	0.0031 (11)	−0.0072 (11)
C11	0.0487 (15)	0.0491 (15)	0.0419 (15)	0.0061 (12)	0.0063 (12)	−0.0059 (12)
C12	0.0621 (18)	0.0551 (17)	0.0444 (16)	−0.0004 (14)	0.0028 (14)	−0.0153 (13)
C13	0.0510 (17)	0.0602 (18)	0.0581 (19)	−0.0117 (14)	−0.0029 (14)	−0.0109 (15)
C14	0.0427 (15)	0.0538 (16)	0.0524 (17)	−0.0013 (12)	0.0076 (12)	−0.0038 (13)
C15	0.0575 (19)	0.083 (2)	0.075 (2)	0.0027 (17)	0.0269 (16)	−0.0150 (18)
C16	0.090 (3)	0.103 (3)	0.148 (4)	−0.001 (2)	0.025 (3)	0.045 (3)

Cl1—C3	1.730 (2)	C5—C6	1.377 (3)
Cl2—C5	1.736 (2)	C6—H6	0.93
O1—C2	1.344 (3)	C7—H7	0.93
O1—H1	0.82	C8—C9	1.490 (3)
O2—C8	1.219 (3)	C9—C14	1.382 (3)
O3—C11	1.367 (3)	C9—C10	1.393 (3)
O3—C15	1.417 (3)	C10—C11	1.381 (3)
O4—C16	1.369 (4)	C10—H10	0.93
O4—H4	0.82	C11—C12	1.381 (3)
N1—C7	1.273 (3)	C12—C13	1.358 (4)
N1—N2	1.371 (3)	C12—H12	0.93
N2—C8	1.364 (3)	C13—C14	1.381 (4)
N2—H2	0.899 (10)	C13—H13	0.93
C1—C6	1.390 (3)	C14—H14	0.93
C1—C2	1.402 (3)	C15—H15A	0.96
C1—C7	1.455 (3)	C15—H15B	0.96
C2—C3	1.393 (3)	C15—H15C	0.96
C3—C4	1.379 (3)	C16—H16A	0.96
C4—C5	1.374 (3)	C16—H16B	0.96
C4—H4A	0.93	C16—H16C	0.96
C2—O1—H1	109.5	C14—C9—C10	120.3 (2)
C11—O3—C15	118.7 (2)	C14—C9—C8	116.0 (2)
C16—O4—H4	109.5	C10—C9—C8	123.7 (2)
C7—N1—N2	120.9 (2)	C11—C10—C9	119.0 (2)
C8—N2—N1	115.25 (19)	C11—C10—H10	120.5
C8—N2—H2	127.0 (19)	C9—C10—H10	120.5
N1—N2—H2	117.7 (19)	O3—C11—C10	124.3 (2)
C6—C1—C2	119.6 (2)	O3—C11—C12	115.3 (2)
C6—C1—C7	119.6 (2)	C10—C11—C12	120.4 (2)
C2—C1—C7	120.8 (2)	C13—C12—C11	120.3 (2)
O1—C2—C3	118.0 (2)	C13—C12—H12	119.9
O1—C2—C1	123.7 (2)	C11—C12—H12	119.9
C3—C2—C1	118.2 (2)	C12—C13—C14	120.7 (2)
C4—C3—C2	122.0 (2)	C12—C13—H13	119.7
C4—C3—Cl1	119.52 (18)	C14—C13—H13	119.7
C2—C3—Cl1	118.44 (18)	C13—C14—C9	119.5 (2)
C5—C4—C3	118.8 (2)	C13—C14—H14	120.3
C5—C4—H4A	120.6	C9—C14—H14	120.3
C3—C4—H4A	120.6	O3—C15—H15A	109.5
C4—C5—C6	120.9 (2)	O3—C15—H15B	109.5
C4—C5—Cl2	119.08 (19)	H15A—C15—H15B	109.5
C6—C5—Cl2	119.97 (19)	O3—C15—H15C	109.5
C5—C6—C1	120.4 (2)	H15A—C15—H15C	109.5
C5—C6—H6	119.8	H15B—C15—H15C	109.5
C1—C6—H6	119.8	O4—C16—H16A	109.5
N1—C7—C1	118.4 (2)	O4—C16—H16B	109.5
N1—C7—H7	120.8	H16A—C16—H16B	109.5
C1—C7—H7	120.8	O4—C16—H16C	109.5
O2—C8—N2	120.4 (2)	H16A—C16—H16C	109.5
O2—C8—C9	122.0 (2)	H16B—C16—H16C	109.5
N2—C8—C9	117.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.899 (10)	1.997 (12)	2.881 (3)	167 (3)
O4—H4···O2	0.82	2.35	2.989 (3)	135
O4—H4···O2ii	0.82	2.34	3.023 (3)	141
O1—H1···N1	0.82	1.84	2.557 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.899 (10)	1.997 (12)	2.881 (3)	167 (3)
O4—H4⋯O2	0.82	2.35	2.989 (3)	135
O4—H4⋯O2ii	0.82	2.34	3.023 (3)	141
O1—H1⋯N1	0.82	1.84	2.557 (3)	145

Symmetry codes: (i) ; (ii) .