(E)-3-Bromo-N′-(4-methoxy­benzyl­idene)benzohydrazide methanol solvate

Guo-Biao Cao

doi:10.1107/S1600536809030219

. 2009 Aug 8;65(Pt 9):o2086. doi: 10.1107/S1600536809030219

(E)-3-Bromo-N′-(4-methoxybenzylidene)benzohydrazide methanol solvate

Guo-Biao Cao ^a,^*

PMCID: PMC2970086 PMID: 21577504

Abstract

The title compound, C₁₅H₁₃BrN₂O₂·CH₃OH, was synthesized by the reaction of 4-methoxybenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The benzohydrazide molecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.0 (2)°. The benzohydrazide and methanol molecules are linked into a chain propagating along the b axis by O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds.

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 ▶); Qu & Cao (2009 ▶); Cao & Wang (2009 ▶); Cao (2009 ▶).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₂·CH₄O
M _r = 365.23
Monoclinic,
a = 13.585 (1) Å
b = 6.715 (1) Å
c = 18.377 (1) Å
β = 104.429 (2)°
V = 1623.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.55 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.630, T _max = 0.672
9539 measured reflections
3539 independent reflections
2132 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.103
S = 1.02
3539 reflections
205 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.52 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/S1600536809030219/ci2872sup1.cif

e-65-o2086-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030219/ci2872Isup2.hkl

e-65-o2086-Isup2.hkl^{(173.6KB, 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—H3⋯O1	0.82	2.07	2.831 (3)	154
O3—H3⋯N2	0.82	2.60	3.211 (3)	132
N1—H1⋯O3ⁱ	0.90 (1)	2.12 (1)	2.993 (3)	166 (3)
C6—H6⋯O3ⁱ	0.93	2.49	3.406 (4)	168
C8—H8⋯O3ⁱ	0.93	2.56	3.370 (3)	146

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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 an interesting topic in structural chemistry. Recently, crystal structures of a 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; Qu & Cao, 2009; Cao & Wang, 2009), the title new hydrazone compound derived from the reaction of 2-chlorobenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide is reported.

The title compound (Fig. 1) consists of a hydrazone molecule and a methanol molecule of crystallization. The methanol molecule is linked to the hydrazone molecule through O—H···O and O—H···N hydrogen bonds (Table 1). The hydrazone molecule displays an E configuration about the C═N bond. The dihedral angle between the two benzene rings is 4.0 (2)°. In the crystal structure, molecules are linked through intermolecular N—H···O, O—H···O, O—H···N and C—H···O hydrogen bonds (Table 1) to form chains running along the b axis (Fig. 2).

Experimental

The title compound was prepared by refluxing equimolar quantities of 4-methoxybenzaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed by slow evaporation of the solution in air.