4-Meth­oxy-N′-(2-methoxy­benzyl­idene)benzohydrazide

Xinyou Zhang

doi:10.1107/S1600536809019102

. 2009 May 23;65(Pt 6):o1388. doi: 10.1107/S1600536809019102

4-Methoxy-N′-(2-methoxybenzylidene)benzohydrazide

Xinyou Zhang ^a,^*

PMCID: PMC2969810 PMID: 21583235

Abstract

In the title compound, C₁₆H₁₆N₂O₃, the two benzene rings are inclined to one another by 75.4 (2)°, and the molecule adopts an E configuration about the C=N bond. In the crystal structure, symmetry-related molecules are linked via intermolecular N—H⋯O hydrogen bonds, forming chains running parallel to the c axis.

Related literature

For related structures, see: Alhadi et al. (2008 ▶), Küçükgüzel et al. (2003 ▶); Mohd Lair et al. (2009a ▶,b ▶); Li et al. (2009 ▶); Zhang et al. (2009 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₃
M _r = 284.31
Monoclinic,
a = 12.705 (1) Å
b = 16.053 (2) Å
c = 7.718 (1) Å
β = 107.233 (2)°
V = 1503.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.983, T _max = 0.984
8570 measured reflections
3007 independent reflections
1574 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.123
S = 0.98
3007 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.19 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019102/su2114sup1.cif

e-65-o1388-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019102/su2114Isup2.hkl

e-65-o1388-Isup2.hkl^{(147.6KB, 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—H2⋯O2ⁱ	0.898 (9)	1.985 (11)	2.859 (2)	164 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Hydrazone compounds are readily synthesized by the reaction of aldehydes with hydrazides. Recently, a large number of such compounds have been reported on (Alhadi et al., 2008; Küçükgüzel et al., 2003; Li et al., 2009; Zhang et al., 2009). In continuation of work in this area we report herein on the crystal structure of the title compound, a new hydrazone compound synthesized from the reaction of equimolar quantities of 2-methoxybenzaldehyde with 4-methoxybenzohydrazide in methanol.

The molecule structure of the title compound is illustrated in Fig. 1. The molecule adopts an E configuration about the C═N bond. The dihedral angle involving the two benzene rings is 75.4 (2)°. All the bond lengths are within normal values (Allen et al., 1987) and are comparable with those observed in the similar compounds (Mohd Lair et al., 2009a,b).

In the crystal structure of the compound, symmetry related molecules are linked through intermolecular N–H···O and N–H···N hydrogen bonds, forming chains running along the c axis (Table 1 and Fig. 2).

Experimental

2-Methoxybenzaldehyde (1.0 mmol, 136.2 mg) and 4-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were mixed in a methanol solution, and the mixture was refluxed for 1 h. Colorless block-shaped crystals of the title compound were formed by slow evaporation of the solution in air.