N′-(3-Hy­droxy­benzyl­idene)-4-methyl­benzohydrazide

Ji-Lai Liu; Ming-Hui Sun; Jing-Jun Ma

doi:10.1107/S1600536812021897

. 2012 May 19;68(Pt 6):o1816. doi: 10.1107/S1600536812021897

N′-(3-Hydroxybenzylidene)-4-methylbenzohydrazide

Ji-Lai Liu ^a, Ming-Hui Sun ^b, Jing-Jun Ma ^c,^*

PMCID: PMC3379390 PMID: 22719588

Abstract

The title compound, C₁₅H₁₄N₂O₂, was obtained from the reaction of 3-hydroxybenzaldhyde and 4-methylbenzohydrazide in methanol. In the molecule, the benzene rings form a dihedral angle of 2.9 (3)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the molecules into layers parallel to (101). The crystal packing also exhibits π–π interactions between the aromatic rings [centroid–centroid distance = 3.686 (4) Å].

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ▶); Horiuchi et al. (2009 ▶). For benzohydrazide coordination compounds, see: El-Dissouky et al. (2010 ▶); Zhang et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010 ▶); Liu et al. (2011 ▶); Zhang et al. (2012 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M _r = 254.28
Monoclinic,
a = 11.5203 (14) Å
b = 8.7228 (12) Å
c = 13.5793 (19) Å
β = 106.889 (2)°
V = 1305.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.985, T _max = 0.987
5767 measured reflections
2193 independent reflections
1013 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.160
S = 0.96
2193 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021897/cv5303sup1.cif

e-68-o1816-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021897/cv5303Isup2.hkl

e-68-o1816-Isup2.hkl^{(107.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812021897/cv5303Isup3.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
N2—H2⋯O2ⁱ	0.90 (1)	2.10 (2)	2.926 (4)	152 (3)
O2—H2B⋯O1ⁱⁱ	0.82	1.91	2.713 (3)	166

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This project was sponsored by the Natural Development Foundation of Hebei Province (grant No. B2011204051), the Development Foundation of the Department of Education of Hebei Province (grant No. 2010137) and the Research Development Foundation of the Agricultural University of Hebei.

supplementary crystallographic information

Comment

Benzohydrazide compounds are well known for their biological activities (El-Sayed et al., 2011; Horiuchi et al., 2009). In addition, benzohydrazide compounds have also been used as versatile ligands in coordination chemistry (El-Dissouky et al., 2010, Zhang et al., 2010). As a contribution to a structural study on hydrazone compounds, we present here the crystal structure of the title compound (I) obtained in the reaction of 3-hydroxybenzaldehyde with 4-methylbenzohydrazide in methanol.

In (I) (Fig. 1), two benzene rings form a dihedral angle of 2.9 (3)°. The bond lengths and angles are within normal ranges (Allen et al., 1987), and agree well with those reported for related compounds (Suleiman Gwaram et al., 2010; Liu et al., 2011; Zhang et al., 2012). Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to (101). The crystal packing exhibits π–π interactions between the aromatic rings [centroid-centroid distance = 3.686 (4) Å].

Experimental

To a methanol solution (20 ml) of 3-hydroxybenzaldehyde (0.1 mmol, 12.2 mg) and 4-methylbenzohydrazide (0.1 mmol, 15.0 mg), a few drops of acetic acid were added. The mixture was refluxed for 1 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and dried in air. Single crystals, suitable for X-ray diffraction, were obtained by slow evaporation of a methanol solution of the product in air.