3-Bromo-N′-(2-hydroxy­benzyl­idene)benzohydrazide

He-Bing Li

doi:10.1107/S1600536808001293

. 2008 Jan 18;64(Pt 2):o465. doi: 10.1107/S1600536808001293

3-Bromo-N′-(2-hydroxybenzylidene)benzohydrazide

He-Bing Li ^a,^*

PMCID: PMC2960222 PMID: 21201491

Abstract

The title molecule, C₁₄H₁₁BrN₂O₂, displays a trans configuration about the C=N and C—N bonds. The dihedral angle between the two benzene rings is 18.5 (3)°. An intramolecular O—H⋯N hydrogen bond is observed. In the crystal structure, the molecules are linked into a chain along the c axis by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Ali et al. (2002 ▶); Allen et al. (1987 ▶); Cukurovali et al. (2002 ▶); Li (2007a ▶,b ▶); Qian et al. (2006 ▶); Qiu et al. (2006 ▶); Tarafder et al. (2002 ▶); Yang (2006 ▶); Yang & Guo (2006 ▶); Zhao (2006 ▶).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₂
M _r = 319.16
Monoclinic,
a = 10.9397 (17) Å
b = 13.672 (2) Å
c = 8.8915 (14) Å
β = 95.882 (2)°
V = 1322.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.11 mm⁻¹
T = 298 (2) K
0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.436, T _max = 0.456 (expected range = 0.377–0.394)
7853 measured reflections
3029 independent reflections
1997 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.106
S = 1.03
3029 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536808001293/ci2553sup1.cif

e-64-0o465-sup1.cif^{(14.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001293/ci2553Isup2.hkl

e-64-0o465-Isup2.hkl^{(148.7KB, 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	1.93	2.639 (3)	145
N2—H2⋯O2ⁱ	0.89 (1)	1.934 (15)	2.806 (3)	165 (4)
C7—H7⋯O2ⁱ	0.93	2.45	3.206 (3)	139

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges a research grant from Xiangnan University.

supplementary crystallographic information

Comment

The compounds derived from the condensation reaction of aromatic carbaldehydes with hydrazides exhibit a wide range of biological activities and applications (Tarafder et al., 2002; Cukurovali et al., 2002; Ali et al., 2002). Herein the author reports the crystal structure of the title compound.

The bond lengths and bond angles in the title molecule (Fig. 1) are within normal ranges (Allen et al., 1987) and comprable with those observed in similar compounds(Qiu et al., 2006; Yang and Guo, 2006; Yang, 2006). The C7?N1 double bond length of 1.284 (3) Å is comparable with that in other Schiff bases (Li, 2007b; Qian et al., 2006; Zhao, 2006). The C8—N2 bond length of 1.348 (3) Å is intermediate between a C–N single bond and a C?N double bond, because of conjugation. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 18.5 (3)°. The molecule adopts a trans configuration about the C7?N1 and C8–N2 bonds.

There is an intramolecular O1—H1···N1 hydrogen bond (Table 1) in the title molecule, as observed in a similar compound (Li, 2007a). In the crystal structure, the molecules are linked into a chain along the c axis by N—H···O and C—H···O hydrogen bonds (Table 2 and Fig.2).

Experimental

Salicylaldehyde (0.1 mmol, 12.2 mg) and 3-bromobenzoic acid hydrazide (0.1 mmol, 21.5 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. Crystals of the title compound were formed by gradual evaporation of the solvent over 12 d at room temperature (yield 71.2%). Analysis found: C 52.45, H 3.53, N 8.86%; calculated for C₁₄H₁₁BrN₂O₂: C 52.69, H 3.47, N 8.78%.