N′-(5-Bromo-2-hy­droxy­benzyl­idene)-3-nitro­benzohydrazide methanol mono­solvate

Chun-Bao Tang

doi:10.1107/S1600536811042553

. 2011 Oct 22;67(Pt 11):o3002. doi: 10.1107/S1600536811042553

N′-(5-Bromo-2-hydroxybenzylidene)-3-nitrobenzohydrazide methanol monosolvate

Chun-Bao Tang ^a,^*

PMCID: PMC3247402 PMID: 22220020

Abstract

In the title compound, C₁₄H₁₀BrN₃O₄·CH₄O, the dihedral angle between the two benzene rings in the hydrazone molecule is 5.8 (3)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. An O—H⋯O hydrogen bond occurs between the hydrazone molecule and the methanol solvent molecule. In the crystal, the components are linked by intermolecular N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₀BrN₃O₄·CH₄O
M _r = 396.20
Triclinic,
a = 6.701 (2) Å
b = 9.492 (3) Å
c = 13.011 (3) Å
α = 105.866 (2)°
β = 92.535 (2)°
γ = 94.496 (2)°
V = 791.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.63 mm⁻¹
T = 298 K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.726, T _max = 0.779
6325 measured reflections
3356 independent reflections
1142 reflections with I > 2σ(I)
R _int = 0.109

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.236
S = 0.93
3356 reflections
223 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.83 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 datablock(s) global, I. DOI: 10.1107/S1600536811042553/qm2037sup1.cif

e-67-o3002-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042553/qm2037Isup2.hkl

e-67-o3002-Isup2.hkl^{(164.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042553/qm2037Isup3.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⋯O5ⁱ	0.90 (1)	2.04 (5)	2.854 (10)	150 (9)
O5—H5⋯O2	0.82	1.90	2.701 (10)	166
O1—H1⋯N1	0.82	1.99	2.700 (10)	144

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Jiaying University research fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Hydrazone compounds have received much attention in biological and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). In the present paper, the author reports the crystal structure of the title new hydrazone compound (Fig. 1).

The compound contains a hydrazone molecule and a methanol molecule of crystallization. The dihedral angle between the two benzene rings in the hydrazone molecule is 5.8 (3)°. An intramolecular O—H···N hydrogen bond generates a S(6) ring motif in the hydrazone molecule (Bernstein et al., 1995). Bond lengths in the compound are normal (Allen et al., 1987) and comparable to those in the similar compounds the author has reported previously (Tang, 2010; Tang, 2011). In the crystal structure, the hydrazone molecules are linked by the methanol molecules through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis (Fig. 2).

Experimental

5-Bromo-2-hydroxybenzaldehyde (0.1 mmol, 20.1 mg) and 3-nitrobenzohydrazide (0.1 mmol, 18.1 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear yellow solution. Yellow needle-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.