3-Bromo-N′-(3,5-dichloro-2-hydroxy­benzyl­idene)benzohydrazide

Chuan-Gao Zhu; Yi-Jun Wei; Qi-Yong Zhu

doi:10.1107/S1600536808041378

. 2008 Dec 10;65(Pt 1):o85. doi: 10.1107/S1600536808041378

3-Bromo-N′-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide

Chuan-Gao Zhu ^a, Yi-Jun Wei ^a,^*, Qi-Yong Zhu ^a

PMCID: PMC2967993 PMID: 21581723

Abstract

The title compound, C₁₄H₉BrCl₂N₂O₂, was prepared by the reaction of 3,5-dichloro-2-hydroxybenzaldehyde and 3-bromobenzohydrazide in methanol. The dihedral angle between the two benzene rings is 13.0 (2)°. An intramolecular O—H⋯N hydrogen bond is observed. The molecules are linked into chains along the c axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff bases, see: Akitsu & Einaga (2006 ▶); Butcher et al. (2005 ▶); Habibi et al. (2007 ▶); Pradeep (2005 ▶). 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. (2007 ▶).

Experimental

Crystal data

C₁₄H₉BrCl₂N₂O₂
M _r = 388.04
Monoclinic,
a = 8.272 (2) Å
b = 22.366 (3) Å
c = 8.237 (2) Å
β = 104.014 (2)°
V = 1478.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.15 mm⁻¹
T = 298 (2) K
0.23 × 0.23 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.495, T _max = 0.513
8590 measured reflections
3224 independent reflections
2144 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.075
S = 0.98
3224 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.29 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/S1600536808041378/ci2740sup1.cif

e-65-00o85-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041378/ci2740Isup2.hkl

e-65-00o85-Isup2.hkl^{(158.2KB, 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	1.88	2.598 (3)	145
N2—H2⋯O2ⁱ	0.89 (1)	2.03 (1)	2.898 (3)	165 (3)

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Symmetry code: (i) Inline graphic .

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 (Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005; Habibi et al., 2007). We have reported a few Schiff bases and their complexes (Wei et al., 2008; Zhu et al., 2007; Wang et al., 2006). In this paper, the crystal structure of a new Schiff base compound is reported.

The C═N bond length in the title molecule (Fig.1) 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 a related compound (Bao & Wei, 2008). The dihedral angle between C1—C6 and C9—C14 phenyl rings is 13.0 (2)°, indicating that the molecule is non-planar. An intramolecular O1—H1···N1 hydrogen bond is observed.

The crystal structure is stabilized by intermolecular N–H···O hydrogen bonds (Table 1), forming chains along the c axis (Fig. 2).

Experimental

3,5-Dichloro-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 5 d, colourless needle-shaped crystals were formed.