2-Chloro-N′-(3,5-dibromo-2-hydroxy­benzyl­idene)benzohydrazide methanol solvate

Chun-Bao Tang

doi:10.1107/S160053680801965X

. 2008 Jul 5;64(Pt 8):o1382. doi: 10.1107/S160053680801965X

2-Chloro-N′-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide methanol solvate

Chun-Bao Tang ^a,^*

PMCID: PMC2962015 PMID: 21203102

Abstract

The title Schiff base compound, C₁₄H₉Br₂ClN₂O₂·CH₄O, was derived from the condensation reaction of 3,5-dibromosalicylaldehyde with 2-chlorobenzohydrazide. The dihedral angle between the two benzene rings is 48.2 (2)°. In the crystal structure, molecules are linked through O—H⋯O and N—H⋯O intermolecular hydrogen bonds, forming layers parallel to the bc plane. There is also an O—H⋯N intramolecular hydrogen bond.

Related literature

For related structures, see: Tang (2006 ▶); Tang, (2007a ▶,b ▶,c ▶,d ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₉Br₂ClN₂O₂·CH₄O
M _r = 464.54
Monoclinic,
a = 11.156 (4) Å
b = 9.696 (3) Å
c = 18.536 (3) Å
β = 120.356 (8)°
V = 1730.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 4.85 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.402, T _max = 0.444 (expected range = 0.343–0.379)
9035 measured reflections
3627 independent reflections
1895 reflections with I > 2σ(I)
R _int = 0.101

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.160
S = 0.92
3627 reflections
215 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.71 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801965X/at2583sup1.cif

e-64-o1382-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801965X/at2583Isup2.hkl

e-64-o1382-Isup2.hkl^{(177.9KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.82	2.05	2.697 (9)	136
N2—H2⋯O3	0.89 (7)	1.946 (17)	2.840 (7)	173 (8)
O1—H1⋯N1	0.82	1.91	2.590 (6)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Jiaying University research fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Recently, the author has reported the structures of several Schiff base compounds (Tang, 2006;Tang, 2007a,b,c,d) and, in continuation of work in this area, reports herein the structure of the title compound, (I), a new Schiff base compound.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 48.2 (2)°. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8, and N1—N2—C8—C9 are 0.1 (2), 4.8 (2), and 4.3 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through O–H···O intermolecular hydrogen bonds (Table 1), forming layers parallel to the bc plane (Fig. 2).

Experimental

3,5-Dibromosalicylaldehyde (0.1 mmol, 28.0 mg) and 2-chlorobenzohydrazide (0.1 mmol, 17.0 mg) were dissolved in a methanol solution (20 ml). The mixture was stirred at reflux for 10 min to give a clear colorless solution. Colourless block-like crystals of the compound were formed by slow evaporation of the solvent over several days.