3-Chloro-N'-(3,5-dibromo-2-hy-droxy-benzyl-idene)benzohydrazide methanol monosolvate.

The title Schiff base compound, C(14)H(9)Br(2)ClN(2)O(2)·CH(3)OH, features an intra-molecular O-H⋯N hydrogen bond, which contributes to the planarity of the mol-ecule: the dihedral angle between the two benzene rings is 4.6 (2)°. In the crystal, pairs of adjacent mol-ecules are linked through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, forming dimers. The methanol solvent mol-ecule is linked by inter-molecular O-H⋯O hydrogen bonds.

Related literature

For Schiff base compounds derived from the reaction of aldehydes with benzohydrazides, see: Pouralimardan et al. (2007) ▶; Dinda et al. (2002 ▶); Podyachev et al. (2007 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H9Br2ClN2O2·CH4O

M = 464.54

Triclinic,

a = 8.8560 (18) Å

b = 9.3810 (19) Å

c = 11.205 (2) Å

α = 95.634 (3)°

β = 110.952 (3)°

γ = 99.392 (3)°

V = 845.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 4.97 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.468, T max = 0.486

7213 measured reflections

3504 independent reflections

2423 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.117

S = 1.03

3504 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.71 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536811000742/hg2785sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000742/hg2785Isup2.hkl

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

C14H9Br2ClN2O2·CH4O	Z = 2
Mr = 464.54	F(000) = 456
Triclinic, P1	Dx = 1.825 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8560 (18) Å	Cell parameters from 2168 reflections
b = 9.3810 (19) Å	θ = 2.5–25.9°
c = 11.205 (2) Å	µ = 4.97 mm−1
α = 95.634 (3)°	T = 298 K
β = 110.952 (3)°	Block, colorless
γ = 99.392 (3)°	0.18 × 0.17 × 0.17 mm
V = 845.2 (3) Å3

Bruker APEXII CCD area-detector diffractometer	3504 independent reflections
Radiation source: fine-focus sealed tube	2423 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.468, Tmax = 0.486	k = −11→11
7213 measured reflections	l = −14→13

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.050P)2 + 0.0441P] where P = (Fo2 + 2Fc2)/3
3504 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.61 e Å−3
1 restraint	Δρmin = −0.71 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
Br1	0.29523 (6)	0.00200 (5)	1.38779 (5)	0.0684 (2)
Br2	−0.39950 (6)	−0.16848 (6)	1.18451 (5)	0.0754 (2)
Cl1	−0.12376 (13)	0.68386 (11)	0.50390 (9)	0.0538 (3)
N1	0.0467 (4)	0.2942 (3)	0.9916 (3)	0.0375 (7)
N2	0.0405 (4)	0.3784 (3)	0.8978 (3)	0.0386 (7)
O1	0.2266 (3)	0.1922 (3)	1.1849 (3)	0.0496 (7)
H1	0.2078	0.2450	1.1295	0.074*
O2	0.3090 (3)	0.4803 (3)	1.0115 (3)	0.0533 (7)
O3	0.2945 (3)	0.6052 (3)	0.2405 (3)	0.0578 (8)
H3	0.3060	0.5530	0.1826	0.087*
C1	−0.0709 (5)	0.1171 (4)	1.0859 (3)	0.0338 (8)
C2	0.0834 (4)	0.1111 (4)	1.1785 (3)	0.0346 (8)
C3	0.0872 (4)	0.0173 (4)	1.2683 (3)	0.0388 (8)
C4	−0.0538 (5)	−0.0650 (4)	1.2702 (3)	0.0439 (9)
H4	−0.0484	−0.1259	1.3316	0.053*
C5	−0.2040 (5)	−0.0563 (4)	1.1797 (4)	0.0420 (9)
C6	−0.2136 (5)	0.0304 (4)	1.0871 (3)	0.0392 (8)
H6	−0.3162	0.0315	1.0246	0.047*
C7	−0.0839 (4)	0.2091 (4)	0.9867 (3)	0.0356 (8)
H7	−0.1856	0.2058	0.9212	0.043*
C8	0.1846 (4)	0.4709 (4)	0.9153 (3)	0.0349 (8)
C9	0.1854 (4)	0.5574 (4)	0.8114 (3)	0.0341 (8)
C10	0.0427 (4)	0.5745 (3)	0.7138 (3)	0.0349 (8)
H10	−0.0608	0.5274	0.7088	0.042*
C11	0.0560 (5)	0.6615 (4)	0.6248 (3)	0.0388 (8)
C12	0.2061 (5)	0.7299 (4)	0.6284 (4)	0.0503 (10)
H12	0.2126	0.7875	0.5667	0.060*
C13	0.3475 (5)	0.7129 (5)	0.7242 (4)	0.0560 (11)
H13	0.4504	0.7598	0.7279	0.067*
C14	0.3379 (5)	0.6269 (4)	0.8146 (4)	0.0459 (9)
H14	0.4345	0.6151	0.8785	0.055*
C15	0.4103 (6)	0.5924 (6)	0.3610 (4)	0.0718 (14)
H15A	0.5198	0.6338	0.3671	0.108*
H15B	0.4020	0.4907	0.3691	0.108*
H15C	0.3882	0.6438	0.4293	0.108*
H2	−0.060 (3)	0.383 (5)	0.842 (4)	0.086*

	U11	U22	U33	U12	U13	U23
Br1	0.0442 (3)	0.0852 (4)	0.0707 (3)	0.0200 (2)	0.0048 (2)	0.0458 (3)
Br2	0.0454 (3)	0.0852 (4)	0.0891 (4)	−0.0070 (2)	0.0186 (3)	0.0470 (3)
Cl1	0.0495 (6)	0.0638 (6)	0.0440 (6)	0.0160 (5)	0.0074 (5)	0.0251 (5)
N1	0.0416 (18)	0.0382 (16)	0.0383 (17)	0.0134 (14)	0.0164 (15)	0.0195 (13)
N2	0.0362 (18)	0.0394 (16)	0.0402 (18)	0.0099 (14)	0.0104 (15)	0.0198 (14)
O1	0.0347 (15)	0.0582 (17)	0.0538 (17)	0.0050 (13)	0.0113 (13)	0.0294 (13)
O2	0.0344 (15)	0.078 (2)	0.0455 (16)	0.0117 (14)	0.0079 (13)	0.0314 (14)
O3	0.0395 (16)	0.079 (2)	0.0466 (17)	0.0142 (15)	0.0039 (14)	0.0187 (15)
C1	0.042 (2)	0.0317 (18)	0.0286 (18)	0.0103 (15)	0.0115 (16)	0.0120 (14)
C2	0.0297 (19)	0.0355 (19)	0.039 (2)	0.0093 (15)	0.0112 (17)	0.0104 (15)
C3	0.036 (2)	0.041 (2)	0.0352 (19)	0.0115 (17)	0.0050 (17)	0.0148 (16)
C4	0.046 (2)	0.041 (2)	0.046 (2)	0.0125 (18)	0.015 (2)	0.0217 (18)
C5	0.037 (2)	0.041 (2)	0.046 (2)	0.0011 (17)	0.0141 (19)	0.0136 (17)
C6	0.033 (2)	0.042 (2)	0.040 (2)	0.0082 (17)	0.0081 (17)	0.0134 (16)
C7	0.033 (2)	0.0370 (19)	0.0334 (19)	0.0102 (16)	0.0061 (16)	0.0127 (15)
C8	0.0312 (19)	0.0416 (19)	0.036 (2)	0.0130 (16)	0.0136 (17)	0.0146 (15)
C9	0.036 (2)	0.0349 (19)	0.0340 (19)	0.0109 (16)	0.0136 (17)	0.0081 (15)
C10	0.032 (2)	0.039 (2)	0.0345 (19)	0.0081 (16)	0.0123 (17)	0.0110 (16)
C11	0.043 (2)	0.038 (2)	0.036 (2)	0.0135 (17)	0.0119 (18)	0.0121 (16)
C12	0.054 (3)	0.054 (2)	0.056 (2)	0.018 (2)	0.028 (2)	0.029 (2)
C13	0.037 (2)	0.068 (3)	0.070 (3)	0.008 (2)	0.026 (2)	0.031 (2)
C14	0.031 (2)	0.057 (2)	0.052 (2)	0.0115 (18)	0.0152 (19)	0.0227 (19)
C15	0.045 (3)	0.104 (4)	0.055 (3)	0.007 (3)	0.005 (2)	0.031 (3)

Br1—C3	1.889 (3)	C4—H4	0.9300
Br2—C5	1.895 (4)	C5—C6	1.368 (5)
Cl1—C11	1.743 (4)	C6—H6	0.9300
N1—C7	1.274 (4)	C7—H7	0.9300
N1—N2	1.367 (4)	C8—C9	1.484 (4)
N2—C8	1.359 (5)	C9—C14	1.387 (5)
N2—H2	0.90 (4)	C9—C10	1.389 (4)
O1—C2	1.342 (4)	C10—C11	1.374 (4)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.218 (4)	C11—C12	1.363 (6)
O3—C15	1.404 (5)	C12—C13	1.373 (6)
O3—H3	0.8200	C12—H12	0.9300
C1—C6	1.392 (5)	C13—C14	1.373 (5)
C1—C2	1.403 (5)	C13—H13	0.9300
C1—C7	1.457 (4)	C14—H14	0.9300
C2—C3	1.396 (5)	C15—H15A	0.9600
C3—C4	1.366 (5)	C15—H15B	0.9600
C4—C5	1.375 (5)	C15—H15C	0.9600
C7—N1—N2	120.4 (3)	O2—C8—N2	121.2 (3)
C8—N2—N1	115.9 (3)	O2—C8—C9	121.3 (3)
C8—N2—H2	125 (3)	N2—C8—C9	117.4 (3)
N1—N2—H2	118 (3)	C14—C9—C10	118.8 (3)
C2—O1—H1	109.5	C14—C9—C8	117.5 (3)
C15—O3—H3	109.5	C10—C9—C8	123.7 (3)
C6—C1—C2	119.2 (3)	C11—C10—C9	119.4 (3)
C6—C1—C7	119.5 (3)	C11—C10—H10	120.3
C2—C1—C7	121.3 (3)	C9—C10—H10	120.3
O1—C2—C3	118.8 (3)	C12—C11—C10	121.7 (3)
O1—C2—C1	123.0 (3)	C12—C11—Cl1	119.3 (3)
C3—C2—C1	118.3 (3)	C10—C11—Cl1	119.0 (3)
C4—C3—C2	122.0 (3)	C11—C12—C13	119.2 (3)
C4—C3—Br1	119.6 (3)	C11—C12—H12	120.4
C2—C3—Br1	118.4 (3)	C13—C12—H12	120.4
C3—C4—C5	118.8 (3)	C12—C13—C14	120.4 (4)
C3—C4—H4	120.6	C12—C13—H13	119.8
C5—C4—H4	120.6	C14—C13—H13	119.8
C6—C5—C4	121.2 (3)	C13—C14—C9	120.5 (4)
C6—C5—Br2	120.2 (3)	C13—C14—H14	119.7
C4—C5—Br2	118.6 (3)	C9—C14—H14	119.7
C5—C6—C1	120.4 (4)	O3—C15—H15A	109.5
C5—C6—H6	119.8	O3—C15—H15B	109.5
C1—C6—H6	119.8	H15A—C15—H15B	109.5
N1—C7—C1	118.7 (3)	O3—C15—H15C	109.5
N1—C7—H7	120.6	H15A—C15—H15C	109.5
C1—C7—H7	120.6	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.90 (4)	1.98 (2)	2.852 (4)	165 (5)
O3—H3···O2ii	0.82	1.98	2.769 (4)	161
O1—H1···N1	0.82	1.85	2.566 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.90 (4)	1.98 (2)	2.852 (4)	165 (5)
O3—H3⋯O2ii	0.82	1.98	2.769 (4)	161
O1—H1⋯N1	0.82	1.85	2.566 (4)	146

Symmetry codes: (i) ; (ii) .