N′-(2-Chloro-5-nitro­benzyl­idene)-3-hydroxy­benzohydrazide methanol solvate

Zhi Zhou

doi:10.1107/S1600536808019636

. 2008 Jul 5;64(Pt 8):o1383. doi: 10.1107/S1600536808019636

N′-(2-Chloro-5-nitrobenzylidene)-3-hydroxybenzohydrazide methanol solvate

Zhi Zhou ^a,^*

PMCID: PMC2962016 PMID: 21203103

Abstract

In the title compound, C₁₄H₁₀ClN₃O₄·CH₃OH, the dihedral angle between the two benzene rings is 33.9 (2)°. In the crystal structure, the methanol solvent molecules are linked to the Schiff base molecules through intermolecular N—H⋯O and O—H⋯O hydrogen bonds. Molecules are further linked through intermolecular O—H⋯O and O—H⋯N hydrogen bonds, forming chains running along the b axis.

Related literature

For related structures, see: Zhou & Tang (2007 ▶); Zhou & Xiao (2007 ▶). For related literature, see: Ali et al. (2007 ▶); Butcher et al. (2007 ▶); He (2008 ▶); Jing & Yu (2007 ▶); Nie (2008 ▶).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₄·CH₄O
M _r = 351.74
Monoclinic,
a = 7.716 (3) Å
b = 11.945 (2) Å
c = 17.650 (3) Å
β = 99.886 (2)°
V = 1602.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 (2) K
0.27 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.931, T _max = 0.943
12656 measured reflections
3316 independent reflections
2396 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.121
S = 1.01
3316 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 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/S1600536808019636/rz2226sup1.cif

e-64-o1383-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019636/rz2226Isup2.hkl

e-64-o1383-Isup2.hkl^{(162.7KB, 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
O4—H4⋯O3ⁱ	0.82	1.91	2.7237 (19)	169
O4—H4⋯N2ⁱ	0.82	2.62	3.118 (2)	120
O5—H5⋯O3ⁱ	0.82	2.00	2.817 (2)	175
N3—H3B⋯O5	0.81 (3)	2.05 (3)	2.854 (2)	173 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author thanks Kaili College for financial support.

supplementary crystallographic information

Comment

Recently, we have reported two metal complexes with Schiff base ligands (Zhou & Tang, 2007; Zhou & Xiao, 2007). We report herein the crystal structure of the title Schiff base compound (Fig. 1).

The title compound consists of a Schiff base molecule and a methanol molecule of crystallization. The dihedral angle between the two benzene rings is 33.9 (2)°. All bond lengths are comparable to those found in similar compounds (Ali et al., 2007; Nie, 2008; He, 2008; Butcher et al., 2007; Jing & Yu, 2007). In the crystal structure, the methanol molecules are linked to the Schiff base molecules through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1). Molecules are further linked through intermolecular O—H···O and O—H···N hydrogen bonds to form chains running along the b axis (Fig. 2).

Experimental

2-Chloro-5-nitrobenzaldehyde (1.0 mmol, 167.1 mg) and 3-hydroxybenzohydrazide (1.0 mmol, 152.1 mg) were dissolved in methanol (30 ml). The mixture was stirred at reflux for 30 min to give a colourless solution. After keeping the solution in air for a few days, colourless block-shaped crystals were formed.