(E)-N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]-3-methoxy­benzohydrazide

Cong-Ming Li; Hong-Yan Ban

doi:10.1107/S1600536809010228

. 2009 Mar 28;65(Pt 4):o876. doi: 10.1107/S1600536809010228

(E)-N′-[1-(2-Hydroxyphenyl)ethylidene]-3-methoxybenzohydrazide

Cong-Ming Li ^a,^*, Hong-Yan Ban ^b

PMCID: PMC2968921 PMID: 21582587

Abstract

In the title compound, C₁₆H₁₆N₂O₃, the benzohydrazide group is not planar and the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 26.9 (2)°. In the crystal structure, the molecular packing is stabilized by intramolecular O—H⋯N and intermolecular N—H⋯O hydrogen bonds. The intermolecular hydrogen bonding forms chains parallel to the b axis.

Related literature

For the biological activities of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban & Li (2008a ▶,b ▶); Yehye et al. (2008 ▶); Fun et al. (2008a ▶,b ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₃
M _r = 284.31
Orthorhombic,
a = 12.932 (2) Å
b = 8.756 (2) Å
c = 25.784 (3) Å
V = 2919.7 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.27 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.976, T _max = 0.982
22735 measured reflections
3180 independent reflections
2023 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.145
S = 1.01
3180 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010228/bx2198sup1.cif

e-65-0o876-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010228/bx2198Isup2.hkl

e-65-0o876-Isup2.hkl^{(156.1KB, 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	0.897 (10)	2.010 (11)	2.894 (2)	168 (2)
O1—H1⋯N1	0.82	1.82	2.534 (2)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support of this work was provided by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Hydrazones derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of hydrazones have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported two hydrazones (Ban & Li, 2008a,b). In this paper, we report herein the crystal structure of the title compound, (I). In the structure of (I), Fig. 1, the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 26.9 (2)°. In the 3-methoxyphenyl unit, the methoxy group is nearly coplanar with the mean plane of the C10–C15 ring, with the C16 atom deviates from the plane by 0.024 (2) Å. The torsion angle of C7-N1-N2-C9 is 8.0 (3)°. In the crystal structure the molecular packing is stabilized by intramolecular O-H···N and intermolecular N—H···O hydrogen bonds, Table 1. The intermolecular hydrogen bond form chains parallel to the b axis, Fig. 2.

Experimental

The compound was prepared by refluxing 1-(2-hydroxyphenyl)ethanone (1.0 mol, 0136 g ) with 3-methoxybenzohydrazide (1.0 mol), 0166 g) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colorless solid product was filtered, and washed three times with methanol. Colorless block crystals of the title compound were obtained from a methanol solution by slow evaporation in air.