N′-(5-Bromo-2-hy­droxy­benzyl­idene)-4-nitro­benzohydrazide methanol monosolvate

Wei-Hua Liu; Shuang-Ju Song; Jing-Jun Ma

doi:10.1107/S1600536811030108

. 2011 Jul 30;67(Pt 8):o2198. doi: 10.1107/S1600536811030108

N′-(5-Bromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol monosolvate

Wei-Hua Liu ^a, Shuang-Ju Song ^a, Jing-Jun Ma ^a,^*

PMCID: PMC3213628 PMID: 22091205

Abstract

In the title compound, C₁₄H₁₀BrN₃O₄·CH₄O, the benzohydrazide molecule is nearly planar [maximum deviation = 0.110 (2) Å]. The mean planes of the two benzene rings make a dihedral angle of 8.4 (3)°. In the benzohydrazide molecule, there is an intramolecular O—H⋯N hydrogen bond and the NH group is hydrogen bonded to the methanol solvent molecule. In the crystal, intermolecular O—H⋯O hydrogen bonds involving the methanol solvent molecule link the benzohydrazide molecules to form chains which propagate along the a axis.

Related literature

For the biological activities of benzohydrazide compounds, see: El-Sayed et al. (2011 ▶); Horiuchi et al. (2009 ▶). For coordination compounds of benzohydrazide compounds, see: El-Dissouky et al. (2010 ▶); Zhang et al. (2010 ▶). For standard bond distances, see: Allen et al. (1987 ▶). For related structures, see: Suleiman Gwaram et al. (2010 ▶); Dai & Mao (2010 ▶); Ban (2010 ▶).

Experimental

Crystal data

C₁₄H₁₀BrN₃O₄·CH₄O
M _r = 396.20
Monoclinic,
a = 6.660 (2) Å
b = 19.068 (3) Å
c = 12.730 (2) Å
β = 93.222 (2)°
V = 1614.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.58 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.668, T _max = 0.747
8673 measured reflections
3442 independent reflections
1824 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.101
S = 0.95
3442 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811030108/su2299sup1.cif

e-67-o2198-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030108/su2299Isup2.hkl

e-67-o2198-Isup2.hkl^{(168.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811030108/su2299Isup3.cml

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⋯O5	0.89 (1)	2.00 (2)	2.875 (4)	166 (4)
O1—H1⋯N1	0.82	2.03	2.737 (4)	143
O1—H1⋯O5ⁱ	0.82	2.51	2.952 (4)	115
O5—H5⋯O2ⁱⁱ	0.82	1.90	2.710 (4)	171

Open in a new tab

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

Acknowledgments

This project was sponsored by the Nature Development Foundation of Hebei Province (gant No. B2011204051), the Development Foundation of the Department of Education of Hebei Province (grant No. 2010137) and the Research Development Foundation of the Agricultural University of Hebei.

supplementary crystallographic information

Comment

Benzohydrazide compounds are well known for their biological activities (El-Sayed et al., 2011; Horiuchi et al., 2009). In addition, benzohydrazide compounds have also been used as versatile ligands in coordination chemistry (El-Dissouky et al., 2010, Zhang et al., 2010). As a contribution to a structural study on hydrazone compounds, we present here the crystal structure of the title compound, that was obtained as the product of the reaction of 5-bromosalicylaldehyde with 4-nitrobenzohydrazide in methanol.

The title compound contains a benzohydrazide molecule and a methanol solvent molecule of crystallization (Fig. 1). In the benzohydrazide molecule there is an intramolecular O-H···N hydrogen bond and NH group is hydrogen bonded to the methanol solvate molecule. The bond distances (Allen et al., 1987) and angles are within normal ranges and agree well with the corresponding bond distances and angles reported in closely related compounds (Suleiman Gwaram et al., 2010; Dai & Mao, 2010; Ban, 2010). The benzohydrazide molecule is nearly planar [maximum deviation of 0.110 (2) Å], with the mean planes of the two benzene rings making a dihedral angle of 8.4 (3)°.

In the crystal, intermolecular O—H···O hydrogen bonds involving the methanol solvate molecule link the benzohydrazide molecules to form chains which propagate along along the a axis direction (Table 1, Fig. 2).

Experimental

To a methanol solution (20 ml) of 5-bromosalicylaldehyde (0.1 mmol, 20.1 mg) and 4-nitrobenzohydrazide (0.1 mmol, 18.1 mg), a few drops of acetic acid were added. The mixture was refluxed for 1 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and dried in air. Single crystals, suitable for X-ray diffraction, were obtained by slow evaporation of a methanol solution of the product in air.