N′-(4-Methoxy­benzyl­idene)-4-nitro­benzo­hydrazide methanol solvate

Yuan-Zhi Wang; Ming-Dong Wang; Yun-Peng Diao; Qian Cai

doi:10.1107/S1600536808005813

. 2008 Mar 5;64(Pt 4):o668. doi: 10.1107/S1600536808005813

N′-(4-Methoxybenzylidene)-4-nitrobenzohydrazide methanol solvate

Yuan-Zhi Wang ^a,^b, Ming-Dong Wang ^b, Yun-Peng Diao ^c,^*, Qian Cai ^a,^*

PMCID: PMC2960903 PMID: 21202062

Abstract

The title compound, C₁₅H₁₃N₃O₄·CH₄O, was synthesized from the reaction of 4-methoxybenzaldehyde with 4-nitrobenzohydrazide in methanol. The benzene rings of the Schiff base molecule are nearly coplanar, making a dihedral angle of 7.0 (3)°. The methanol solvent molecules are linked to the Schiff base molecules by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, forming chains running parallel to the b axis.

Related literature

For related structures, see: Brückner et al. (2000 ▶); Diao (2007 ▶); Diao et al. (2007 ▶, 2008 ▶); Harrop et al. (2003 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₄·CH₄O
M _r = 331.33
Monoclinic,
a = 14.719 (3) Å
b = 6.631 (2) Å
c = 18.002 (3) Å
β = 113.17 (3)°
V = 1615.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.27 × 0.23 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.973, T _max = 0.977
9171 measured reflections
3351 independent reflections
1493 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.172
S = 0.95
3351 reflections
224 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536808005813/rz2199sup1.cif

e-64-0o668-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005813/rz2199Isup2.hkl

e-64-0o668-Isup2.hkl^{(164.4KB, 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—H2A⋯O5	0.897 (10)	2.049 (13)	2.921 (3)	164 (3)
O5—H5⋯N3ⁱ	0.82	2.56	3.167 (3)	133
O5—H5⋯O3ⁱ	0.82	2.10	2.863 (3)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

This project is supported by a research grant from Dalian Medical University.

supplementary crystallographic information

Comment

Schiff base compounds have been found to have potential pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). Recently, a few Schiff base compounds derived from the reaction of aldehydes with benzohydrazides have been reported (Diao et al., 2008; Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007). As a further study of such compounds, we report here the structure of the title compound.

The title compound (Fig. 1) consists of a Schiff base molecule and a lattice methanol molecule. The Schiff base molecule is nearly planar with the dihedral angle between the two phenyl rings of 7.0 (3)°. The dihedral angle between the C1—C6 phenyl ring and the O1/N1/O2 nitryl plane is 5.1 (3)°. The torsion angles C9—C8—N3—N2 and C4—C7—N2—N3 are 1.4 (3) and 1.6 (3)°, respectively. The methanol molecules are linked to the Schiff base molecules by N–H···O, O–H···N and O–H···O hydrogen bonds (Table 1) forming chains running parallel to the b axis.

Experimental

4-Methoxybenzaldehyde (0.1 mmol, 13.6 mg) and 4-nitrobenzohydrazide (0.1 mmol, 18.1 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 1 h and cooled to room temperature. After keeping the solution in air for five days, yellow block-like crystals were formed on slow evaporation of the solvent.