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

Yi-Jun Wei; Feng-Wu Wang; Qi-Yong Zhu

doi:10.1107/S1600536809007466

. 2009 Mar 6;65(Pt 4):o688. doi: 10.1107/S1600536809007466

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

Yi-Jun Wei ^a,^*, Feng-Wu Wang ^a, Qi-Yong Zhu ^a

PMCID: PMC2968809 PMID: 21582430

Abstract

The title compound, C₁₄H₉Br₃N₂O₂·CH₄O, was prepared by the reaction of 3,5-dibromo-2-hydroxybenzaldehyde and 3-bromobenzohydrazide in methanol. The asymmetric unit of the crystal consists of a Schiff base molecule and a methanol molecule of crystallization. The dihedral angle between the two benzene rings is 5.5 (2)°. An intramolecular O—H⋯N hydrogen bond is observed. In the crystal structure, pairs of adjacent Schiff base molecules are linked by two methanol molecules through intermolecular 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 _r = 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
Δρ_max = 0.45 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-65-0o688-sup1.cif^{(16.2KB, cif)}

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

e-65-0o688-Isup2.hkl^{(176.8KB, 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
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)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Natural Science Foundation of the Education Office of Anhui Province, China, for financial support (grant No. KJ2007A126ZC).

supplementary crystallographic information

Comment

Schiff bases are readily synthesized by the reaction of aldehydes with primary amines (Lodeiro et al., 2003; Annigeri et al., 2002; Rao et al., 2003). We have previously reported some Schiff bases and their complexes (Wei et al., 2008; Wang et al., 2006). In this paper, the preparation and crystal structure of the new Schiff base title compound (I), Fig 1, is reported.

The C═N bond length in the title molecule is comparable with those observed in other Schiff bases (Yehye et al., 2008; Odabaşoğlu et al., 2007; Yathirajan et al., 2007). All bond lengths are within normal ranges and are comparable to those observed in the related compounds (Zhu et al., 2009; Bao & Wei, 2008). The dihedral angle between C1—C6 and C9—C14 phenyl rings is 5.5 (2)°, indicating that the molecule is nearly coplanar. An intramolecular O1—H1···N1 hydrogen bond is observed and may contribute to the overall planarity of the molecule.

In the crystal structure, pairs of adjacent Schiff base molecules are linked by two methanol molecules through intermolecular N2—H2···O3 and O3—H3···O2 hydrogen bonds, Table 1, Fig. 2.

Experimental

3,5-Dibromo-2-hydroxybenzaldehyde (1.0 mmol) and 3-bromobenzohydrazide (1.0 mmol) were dissolved in methanol (30 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. After keeping this solution in air for a week, colourless block-shaped crystals were formed.