(E)-3-Bromo-N′-(2-chloro­benzyl­idene)benzohydrazide

Lan-Zhu Qu; Guo-Biao Cao

doi:10.1107/S160053680902412X

. 2009 Jun 27;65(Pt 7):o1705. doi: 10.1107/S160053680902412X

(E)-3-Bromo-N′-(2-chlorobenzylidene)benzohydrazide

Lan-Zhu Qu ^a, Guo-Biao Cao ^a,^*

PMCID: PMC2969211 PMID: 21582957

Abstract

The title compound, C₁₄H₁₀BrClN₂O, was synthesized by the reaction of 2-chlorobenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The molecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.0 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains propagating along the c axis.

Related literature

For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Li & Ban (2009 ▶); Zhu et al. (2009 ▶); Yang (2007 ▶); You et al. (2008 ▶). For hydrazone compounds reported previously by our group, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶); Cao & Lu (2009a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₀BrClN₂O
M _r = 337.60
Monoclinic,
a = 13.140 (1) Å
b = 12.632 (1) Å
c = 8.377 (1) Å
β = 98.174 (2)°
V = 1376.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.17 mm⁻¹
T = 298 K
0.27 × 0.25 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.481, T _max = 0.542 (expected range = 0.442–0.498)
8319 measured reflections
2998 independent reflections
2235 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.076
S = 1.03
2998 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902412X/ci2833sup1.cif

e-65-o1705-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902412X/ci2833Isup2.hkl

e-65-o1705-Isup2.hkl^{(147.1KB, 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
N2—H2⋯O1ⁱ	0.89 (1)	1.98 (1)	2.854 (2)	165 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The Vital Foundation of Ankang University (Project No. 2008AKXY012) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02 J K202) are gratefully acknowledged.

supplementary crystallographic information

Comment

Study on the crystal structures of hydrazone derivatives is a hot topic in structural chemistry. In the last few years, the crystal structures of a large number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008; Cao & Lu, 2009a,b), the title new hydrazone compound derived from the reaction of 2-chlorobenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide is reported.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 13.0 (2)°. The molecule displays an E configuration about the C═N bond. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

Experimental

The title compound was prepared by refluxing equimolar quantities of 2-chlorobenzaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed by slow evaporation of the solution in air.