N′-(2-Methoxy­benzyl­idene)-2-nitro­benzo­hydrazide

Ge-Jiang Xiao; Chao Wei

doi:10.1107/S1600536809005753

. 2009 Feb 21;65(Pt 3):o577. doi: 10.1107/S1600536809005753

N′-(2-Methoxybenzylidene)-2-nitrobenzohydrazide

Ge-Jiang Xiao ^a,^*, Chao Wei ^a

PMCID: PMC2968637 PMID: 21582232

Abstract

The title compound, C₁₅H₁₃N₃O₄, was synthesized by the reaction of equimolar quantities of 2-methoxybenzaldehyde and 2-nitrobenzohydrazide in methanol. The dihedral angle between the two substituted benzene rings is 68.3 (2)°. In the crystal structure, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur.

Related literature

For the pharmacological properties of hydrazone compounds, see: Beraldo & Gambino (2004 ▶). For related structures, see: Galić et al. (2001 ▶); Richardson & Bernhardt (1999 ▶); Ali et al. (2004 ▶). For bond length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M _r = 299.28
Triclinic,
a = 7.491 (2) Å
b = 9.427 (3) Å
c = 10.977 (3) Å
α = 91.748 (4)°
β = 106.218 (4)°
γ = 92.221 (4)°
V = 743.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.23 × 0.23 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.978, T _max = 0.979
6232 measured reflections
3140 independent reflections
2018 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.132
S = 1.03
3140 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.20 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/S1600536809005753/sj2574sup1.cif

e-65-0o577-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005753/sj2574Isup2.hkl

e-65-0o577-Isup2.hkl^{(154KB, 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
N1—H1⋯O1ⁱ	0.910 (9)	1.943 (10)	2.844 (2)	170.3 (18)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by Changsha University of Science and Technology (project No. 1004091).

supplementary crystallographic information

Comment

Hydrazone compounds have received considerable attention due to their pharmacological properties (Beraldo & Gambino, 2004). In the last few years, the crystal structures and properties of a series of hydrazone compounds have been reported (Galić et al., 2001; Richardson & Bernhardt, 1999; Ali et al., 2004). As a continuation of work on these compounds, we report here the structure of the title compound, (I) Fig. 1.

In (I), the dihedral angle between the C1—C6 and C9—C14 benzene rings is 111.7 (2)° while that between the O2—N3—O3 nitro plane and the plane of the C1—C6 benzene ring is 26.7 (2)°. Bond lengths in the compound are found to have normal values (Allen et al., 1987). The methoxy group is coplanar with the C9—C14 benzene ring, with a C15—O4—C10—C11 torsion angle of -3.2 (2)°.

In the crystal packing, adjacent molecules are linked through intermolecular N1–H1···O1 hydrogen bonds (Table 1), forming dimers (Fig. 2).

Experimental

The title compound was synthesized by the reaction of equimolar quantities (1.0 mmol each) of 2-methoxybenzaldehyde and 2-nitrobenzohydrazide in methanol (100 ml) for 3 h at room temperature. The solution was kept in air for a few days, forming colorless block-like crystals of the compound.