N′-(2-Hy­droxy­benzyl­idene)-3-methyl­benzohydrazide

Zeng-Xin Liu

doi:10.1107/S1600536811049944

. 2011 Nov 25;67(Pt 12):o3439. doi: 10.1107/S1600536811049944

N′-(2-Hydroxybenzylidene)-3-methylbenzohydrazide

Zeng-Xin Liu ^a,^*

PMCID: PMC3239072 PMID: 22199920

Abstract

The title compound, C₁₅H₁₄N₂O₂, is the product of the reaction of 2-hydroxybenzaldehyde and 3-methylbenzohydrazide. The dihedral angle between the substituted benzene rings is 19.5 (3)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O hydrogen bonds to generate C(4) chains propagating in [001] and C—H⋯O interactions to the same O-atom acceptor reinforce the chains.

Related literature

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

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M _r = 254.28
Monoclinic,
a = 11.042 (2) Å
b = 13.588 (3) Å
c = 8.7936 (15) Å
β = 94.406 (2)°
V = 1315.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.17 × 0.15 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.985, T _max = 0.987
9633 measured reflections
2686 independent reflections
1528 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.186
S = 1.04
2686 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 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/S1600536811049944/hb6528sup1.cif

e-67-o3439-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049944/hb6528Isup2.hkl

e-67-o3439-Isup2.hkl^{(131.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811049944/hb6528Isup3.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
O1—H1⋯N1	0.82	1.91	2.624 (2)	146
N2—H2⋯O2ⁱ	0.90 (1)	1.91 (1)	2.793 (3)	168 (3)
C7—H7⋯O2ⁱ	0.93	2.49	3.229 (2)	137

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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 2-hydroxybenzaldehyde with 3-methylbenzohydrazide, is reported.

The molecule of the compound, Fig. 1, displays a trans-configuration about the C7 ═N1 bond. The torsion angle of C7—N1—N2—C8 is 7.0 (3)°. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 19.5 (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 intermolecular hydrogen bonds (Table 1) to form one-dimensional chains along the c axis (Fig. 2).

Experimental

The title compound was synthesized by the reaction of 2-hydroxybenzaldehyde (1 mmol, 0.12 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.