N′-(2-Chloro­benzyl­idene)-4-hydroxy­benzohydrazide

Yu-Mei Hao

doi:10.1107/S1600536809030797

. 2009 Aug 8;65(Pt 9):o2098. doi: 10.1107/S1600536809030797

N′-(2-Chlorobenzylidene)-4-hydroxybenzohydrazide

Yu-Mei Hao ^a,^*

PMCID: PMC2969926 PMID: 21577514

Abstract

In the molecule of the title compound, C₁₄H₁₁ClN₂O₂, the dihedral angle between the benzene rings is 30.53 (4)°. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules into a two-dimensional network. π–π contacts between benzene rings [centroid–centroid distance = 3.619 (1) Å] may further stabilize the structure. The crystal studied was found to be an inversion twin.

Related literature

For general background, see: Ali et al. (2008 ▶); Dao et al. (2000 ▶); Kargar et al. (2009 ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶); Yeap et al. (2009 ▶). For related structures, see: Eltayeb et al. (2008 ▶); Fun et al. (2009 ▶); Hao (2009 ▶); Nadeem et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M _r = 274.70
Orthorhombic,
a = 7.2851 (17) Å
b = 11.716 (3) Å
c = 14.978 (3) Å
V = 1278.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.30 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 = 0.943, T _max = 0.948
6989 measured reflections
2360 independent reflections
1617 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.105
S = 1.02
2360 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ▶), 963 Friedel pairs
Flack parameter: 0.45 (12)

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/S1600536809030797/hk2750sup1.cif

e-65-o2098-sup1.cif^{(15.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030797/hk2750Isup2.hkl

e-65-o2098-Isup2.hkl^{(116KB, 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
O2—H2⋯O1ⁱ	0.82	1.84	2.657 (3)	179
N2—H2A⋯O2ⁱⁱ	0.90 (3)	2.106 (17)	2.951 (3)	157 (3)

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

supplementary crystallographic information

Comment

Schiff base compounds are a class of important materials used in pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). Schiff bases have also been used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of a large number of Schiff base compounds have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). As a part of our ongoing investigation (Hao, 2009), we report herein the crystal structure of the title new Schiff base compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C9-C14) are, of course, planar and the dihedral angle between them is A/B = 30.53 (4)°.

In the crystal structure, intermolecular O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules into a two-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the benzene rings, Cg1—Cg2ⁱ [symmetry code: (i) 1/2 + x, 1/2 - y, 1 - z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B (C9-C14), respectively] may further stabilize the structure, with centroid-centroid distance of 3.619 (1) Å.

Experimental

For the preparation of the title compound, 2-chlorobenzaldehyde (0.1 mmol, 14.1 mg) and 4-hydroxybenzohydrazide (0.1 mmol, 15.2 mg) were refluxed in a methanol solution (30 ml) for 30 min to give a clear orange solution. Yellow block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.