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

The title compound, C(14)H(9)Br(3)N(2)O(2)·CH(4)O, was prepared by the reaction of 3,5-dibromo-2-hydroxy-benzaldehyde and 3-bromo-benzohydrazide in methanol. The asymmetric unit of the crystal consists of a Schiff base mol-ecule and a methanol mol-ecule of crystallization. The dihedral angle between the two benzene rings is 5.5 (2)°. An intra-molecular O-H⋯N hydrogen bond is observed. In the crystal structure, pairs of adjacent Schiff base mol-ecules are linked by two methanol mol-ecules through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff bases, see: Annigeri et al. (2002 ▶); Lodeiro et al. (2003 ▶); Rao et al. (2003 ▶). For related structures, see: Bao & Wei (2008 ▶); Odabaşoğlu et al. (2007 ▶); Wang et al. (2006 ▶); Wei et al. (2008 ▶); Yathirajan et al. (2007 ▶); Yehye et al. (2008 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C14H9Br3N2O2·CH4O

M = 509.00

Triclinic,

a = 8.900 (1) Å

b = 9.366 (1) Å

c = 11.392 (2) Å

α = 95.043 (2)°

β = 111.048 (2)°

γ = 99.584 (2)°

V = 862.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 7.03 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.216, T max = 0.245

5016 measured reflections

3606 independent reflections

2582 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.084

S = 1.03

3606 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.61 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007466/sj2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007466/sj2587Isup2.hkl

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

C14H9Br3N2O2·CH4O	Z = 2
Mr = 509.00	F(000) = 492
Triclinic, P1	Dx = 1.960 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.900 (1) Å	Cell parameters from 1965 reflections
b = 9.366 (1) Å	θ = 2.5–28.0°
c = 11.392 (2) Å	µ = 7.03 mm−1
α = 95.043 (2)°	T = 298 K
β = 111.048 (2)°	Block, colorless
γ = 99.584 (2)°	0.23 × 0.20 × 0.20 mm
V = 862.6 (2) Å3

Bruker SMART 1000 CCD area-detector diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2582 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.216, Tmax = 0.245	k = −11→11
5016 measured reflections	l = −12→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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0368P)2 + 0.2522P] where P = (Fo2 + 2Fc2)/3
3606 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.45 e Å−3
1 restraint	Δρmin = −0.61 e Å−3

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 > 2sigma(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	0.70334 (5)	1.00574 (5)	−0.37638 (4)	0.07063 (16)
Br2	1.39490 (6)	1.16831 (6)	−0.18075 (5)	0.08319 (19)
Br3	1.13101 (5)	0.31103 (4)	0.49994 (3)	0.05564 (13)
O1	0.7708 (3)	0.8094 (3)	−0.1804 (2)	0.0524 (6)
H1	0.7891	0.7546	−0.1269	0.079*
O2	0.6880 (3)	0.5145 (3)	−0.0140 (2)	0.0564 (7)
O3	0.7124 (3)	0.4000 (3)	0.7628 (2)	0.0634 (7)
H3	0.6886	0.4388	0.8192	0.095*
N1	0.9495 (3)	0.7027 (3)	0.0069 (2)	0.0402 (6)
N2	0.9553 (4)	0.6172 (3)	0.0991 (3)	0.0410 (6)
C1	1.0672 (4)	0.8813 (3)	−0.0850 (3)	0.0351 (7)
C2	0.9137 (4)	0.8887 (4)	−0.1748 (3)	0.0378 (7)
C3	0.9096 (4)	0.9860 (4)	−0.2607 (3)	0.0425 (8)
C4	1.0505 (4)	1.0671 (4)	−0.2633 (3)	0.0449 (8)
H4	1.0450	1.1288	−0.3236	0.054*
C5	1.2002 (4)	1.0569 (4)	−0.1762 (3)	0.0460 (8)
C6	1.2101 (4)	0.9668 (4)	−0.0856 (3)	0.0424 (8)
H6	1.3121	0.9632	−0.0251	0.051*
C7	1.0795 (4)	0.7865 (3)	0.0117 (3)	0.0389 (8)
H7	1.1807	0.7877	0.0755	0.047*
C8	0.8112 (4)	0.5247 (4)	0.0818 (3)	0.0388 (7)
C9	0.8101 (4)	0.4374 (3)	0.1852 (3)	0.0365 (7)
C10	0.6573 (4)	0.3690 (4)	0.1800 (3)	0.0487 (9)
H10	0.5620	0.3809	0.1160	0.058*
C11	0.6468 (5)	0.2827 (5)	0.2705 (4)	0.0607 (11)
H11	0.5442	0.2361	0.2670	0.073*
C12	0.7878 (5)	0.2654 (4)	0.3657 (4)	0.0538 (10)
H12	0.7811	0.2077	0.4268	0.065*
C13	0.9373 (4)	0.3341 (4)	0.3692 (3)	0.0407 (8)
C14	0.9518 (4)	0.4212 (3)	0.2807 (3)	0.0375 (7)
H14	1.0550	0.4679	0.2853	0.045*
C15	0.5947 (6)	0.4070 (6)	0.6437 (4)	0.0784 (14)
H15A	0.5748	0.5045	0.6420	0.118*
H15B	0.4939	0.3389	0.6291	0.118*
H15C	0.6346	0.3822	0.5784	0.118*
H2	1.054 (3)	0.617 (5)	0.159 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0520 (3)	0.0897 (3)	0.0683 (3)	0.0262 (2)	0.0085 (2)	0.0444 (2)
Br2	0.0529 (3)	0.0928 (4)	0.0939 (4)	−0.0098 (2)	0.0193 (2)	0.0505 (3)
Br3	0.0528 (2)	0.0679 (3)	0.0421 (2)	0.01579 (19)	0.00793 (17)	0.02572 (18)
O1	0.0349 (13)	0.0634 (17)	0.0562 (15)	0.0067 (11)	0.0111 (12)	0.0302 (13)
O2	0.0364 (14)	0.0847 (19)	0.0458 (14)	0.0112 (13)	0.0087 (12)	0.0325 (13)
O3	0.0423 (15)	0.087 (2)	0.0534 (15)	0.0155 (14)	0.0067 (13)	0.0188 (15)
N1	0.0430 (16)	0.0410 (16)	0.0396 (14)	0.0114 (13)	0.0152 (13)	0.0199 (12)
N2	0.0402 (16)	0.0463 (16)	0.0387 (15)	0.0110 (13)	0.0132 (13)	0.0220 (13)
C1	0.0383 (18)	0.0363 (17)	0.0315 (16)	0.0076 (14)	0.0131 (14)	0.0099 (13)
C2	0.0372 (18)	0.0398 (18)	0.0363 (17)	0.0108 (15)	0.0117 (15)	0.0102 (14)
C3	0.042 (2)	0.047 (2)	0.0378 (18)	0.0150 (16)	0.0109 (16)	0.0151 (15)
C4	0.052 (2)	0.043 (2)	0.0396 (18)	0.0100 (17)	0.0146 (17)	0.0175 (15)
C5	0.044 (2)	0.044 (2)	0.049 (2)	0.0008 (16)	0.0177 (17)	0.0164 (16)
C6	0.0371 (18)	0.0434 (19)	0.0422 (18)	0.0056 (15)	0.0094 (15)	0.0138 (15)
C7	0.0406 (19)	0.0391 (19)	0.0357 (17)	0.0119 (15)	0.0094 (15)	0.0144 (14)
C8	0.0369 (18)	0.0457 (19)	0.0398 (18)	0.0155 (15)	0.0159 (16)	0.0195 (15)
C9	0.0392 (18)	0.0391 (18)	0.0346 (16)	0.0115 (14)	0.0151 (15)	0.0124 (14)
C10	0.0339 (19)	0.061 (2)	0.054 (2)	0.0124 (17)	0.0155 (17)	0.0246 (18)
C11	0.042 (2)	0.077 (3)	0.073 (3)	0.0102 (19)	0.028 (2)	0.039 (2)
C12	0.052 (2)	0.062 (2)	0.059 (2)	0.0154 (19)	0.0278 (19)	0.0336 (19)
C13	0.0411 (19)	0.046 (2)	0.0342 (16)	0.0104 (16)	0.0113 (15)	0.0130 (15)
C14	0.0329 (17)	0.0427 (19)	0.0374 (17)	0.0066 (14)	0.0135 (14)	0.0118 (14)
C15	0.052 (3)	0.115 (4)	0.056 (2)	0.010 (3)	0.005 (2)	0.034 (3)

Br1—C3	1.886 (3)	C4—H4	0.9300
Br2—C5	1.889 (3)	C5—C6	1.378 (4)
Br3—C13	1.891 (3)	C6—H6	0.9300
O1—C2	1.339 (4)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.494 (4)
O2—C8	1.221 (4)	C9—C14	1.381 (4)
O3—C15	1.400 (4)	C9—C10	1.381 (5)
O3—H3	0.8200	C10—C11	1.385 (5)
N1—C7	1.265 (4)	C10—H10	0.9300
N1—N2	1.367 (3)	C11—C12	1.378 (5)
N2—C8	1.361 (4)	C11—H11	0.9300
N2—H2	0.90 (3)	C12—C13	1.364 (5)
C1—C6	1.388 (5)	C12—H12	0.9300
C1—C2	1.399 (4)	C13—C14	1.378 (4)
C1—C7	1.461 (4)	C14—H14	0.9300
C2—C3	1.390 (4)	C15—H15A	0.9600
C3—C4	1.365 (5)	C15—H15B	0.9600
C4—C5	1.370 (5)	C15—H15C	0.9600
C2—O1—H1	109.5	O2—C8—N2	121.2 (3)
C15—O3—H3	109.5	O2—C8—C9	121.5 (3)
C7—N1—N2	120.2 (3)	N2—C8—C9	117.2 (3)
C8—N2—N1	115.8 (3)	C14—C9—C10	120.4 (3)
C8—N2—H2	125 (3)	C14—C9—C8	123.2 (3)
N1—N2—H2	118 (3)	C10—C9—C8	116.4 (3)
C6—C1—C2	120.0 (3)	C9—C10—C11	119.6 (3)
C6—C1—C7	119.1 (3)	C9—C10—H10	120.2
C2—C1—C7	120.8 (3)	C11—C10—H10	120.2
O1—C2—C3	118.5 (3)	C12—C11—C10	120.3 (3)
O1—C2—C1	123.4 (3)	C12—C11—H11	119.8
C3—C2—C1	118.1 (3)	C10—C11—H11	119.8
C4—C3—C2	121.7 (3)	C13—C12—C11	119.0 (3)
C4—C3—Br1	119.5 (2)	C13—C12—H12	120.5
C2—C3—Br1	118.8 (3)	C11—C12—H12	120.5
C3—C4—C5	119.5 (3)	C12—C13—C14	122.0 (3)
C3—C4—H4	120.2	C12—C13—Br3	119.2 (3)
C5—C4—H4	120.2	C14—C13—Br3	118.8 (2)
C4—C5—C6	120.8 (3)	C13—C14—C9	118.6 (3)
C4—C5—Br2	119.4 (3)	C13—C14—H14	120.7
C6—C5—Br2	119.8 (3)	C9—C14—H14	120.7
C5—C6—C1	119.7 (3)	O3—C15—H15A	109.5
C5—C6—H6	120.2	O3—C15—H15B	109.5
C1—C6—H6	120.2	H15A—C15—H15B	109.5
N1—C7—C1	118.6 (3)	O3—C15—H15C	109.5
N1—C7—H7	120.7	H15A—C15—H15C	109.5
C1—C7—H7	120.7	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.559 (3)	145
O3—H3···O2i	0.82	1.97	2.767 (4)	164
N2—H2···O3ii	0.90 (3)	1.99 (2)	2.848 (4)	160 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.84	2.559 (3)	145
O3—H3⋯O2i	0.82	1.97	2.767 (4)	164
N2—H2⋯O3ii	0.90 (3)	1.986 (18)	2.848 (4)	160 (4)

Symmetry codes: (i) ; (ii) .