N′-(4-Meth­oxy­benzyl­idene)-4-methyl­benzohydrazide

Zeng-Xin Liu

doi:10.1107/S1600536811049932

. 2011 Nov 25;67(Pt 12):o3438. doi: 10.1107/S1600536811049932

N′-(4-Methoxybenzylidene)-4-methylbenzohydrazide

Zeng-Xin Liu ^a,^*

PMCID: PMC3239071 PMID: 22199919

Abstract

The title compound, C₁₆H₁₆N₂O₂, is the product of the reaction of 4-methoxybenzaldehyde and 4-methylbenzohydrazide. The dihedral angle between the substituted benzene rings is 17.6 (3)° and the methoxy C atom is almost coplanar with its attached ring [deviation = 0.019 (4) Å]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating along the b-axis direction.

Related literature

For reference bond lengths, see: Allen et al. (1987 ▶). For related strctures, see: Horkaew et al. (2011 ▶); Fun et al. (2011 ▶); Su et al. (2011 ▶); Hashemian et al. (2011 ▶); Promdet et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₂
M _r = 268.31
Orthorhombic,
a = 12.138 (2) Å
b = 8.0580 (16) Å
c = 29.320 (3) Å
V = 2867.7 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.986, T _max = 0.990
20247 measured reflections
3098 independent reflections
1427 reflections with I > 2σ(I)
R _int = 0.137

Refinement

R[F ² > 2σ(F ²)] = 0.082
wR(F ²) = 0.212
S = 1.01
3098 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811049932/hb6527sup1.cif

e-67-o3438-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049932/hb6527Isup2.hkl

e-67-o3438-Isup2.hkl^{(152.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811049932/hb6527Isup3.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
N1—H1⋯O1ⁱ	0.90 (1)	1.97 (1)	2.870 (4)	176 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author thanks the Experimental Center of Linyi University for support.

supplementary crystallographic information

Comment

Recently, the compounds derived from the condensation reaction of carbonyl-containing compounds with substituted benzohydrazides have received considerable attention. In this paper, the title new compound, derived from the reaction of 4-methoxybenzaldehyde with 4-methylbenzohydrazide, is reported.

The molecule of the compound, Fig. 1, displays a trans-configuration about the C9 ═N2 bond. The torsion angle of C8—N1—N2—C9 is 2.3 (3)°. The dihedral angle between the C2—C7 and C10—C15 benzene rings is 17.6 (3)°, indicating the molecule of the compound is twisted. Overall, the bond distances are within normal values (Allen et al., 1987), and are comparable with those reported in similar compounds (Horkaew et al., 2011; Fun et al., 2011; Su et al., 2011; Hashemian et al., 2011; Promdet et al., 2011). In the crystal, molecules are linked by N—H···O hydrogen bonds (Table 1) to form C(4) chains along the b axis (Fig. 2).

Experimental

The title compound was synthesized by the reaction of 4-methoxybenzaldehyde (1 mmol, 0.14 g) with 4-methylbenzohydrazide (1 mmol, 0.15 g) in absolute methanol (30 ml) at ambient condition. Colorless prism-shaped single crystals were obtained by slow evaporation of the solution at room temperature after several days.