(E)-2-Chloro-N′-(4-hy­droxy­benzyl­idene)­benzohydrazide

Xiao-Yan Li

doi:10.1107/S1600536812005661

. 2012 Feb 17;68(Pt 3):o709. doi: 10.1107/S1600536812005661

(E)-2-Chloro-N′-(4-hydroxybenzylidene)benzohydrazide

Xiao-Yan Li ^a,^*

PMCID: PMC3295484 PMID: 22412595

Abstract

The title hydrazone molecule, C₁₄H₁₁ClN₂O₂, has a trans conformation with respect to the methylidene unit. The dihedral angle between the two benzene rings is 37.6 (3)°. In the crystal, the presence of O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds leads to the formation of a three-dimensional network. The title compound crystallized in the chiral orthorhombic space group P2₁2₁2₁ and was refined as an inversion twin [Flack parameter = −0.20 (18)].

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M _r = 274.70
Orthorhombic,
a = 7.627 (3) Å
b = 11.859 (2) Å
c = 14.297 (2) Å
V = 1293.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.949, T _max = 0.952
6966 measured reflections
2408 independent reflections
1717 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.167
S = 1.07
2408 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ▶), 999 Friedel pairs
Flack parameter: −0.20 (18)

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 datablock(s) global, I. DOI: 10.1107/S1600536812005661/su2376sup1.cif

e-68-0o709-sup1.cif^{(15KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005661/su2376Isup2.hkl

e-68-0o709-Isup2.hkl^{(118.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812005661/su2376Isup3.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
O2—H2⋯O1ⁱ	0.82	1.99	2.751 (4)	155
O2—H2⋯N2ⁱ	0.82	2.48	3.012 (4)	124
N1—H1⋯O2ⁱⁱ	0.90 (1)	2.12 (2)	2.987 (4)	164 (5)

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

Acknowledgments

The author is grateful to the Zibo Vocational Institute for supporting this work.

supplementary crystallographic information

Comment

In recent years, hydrazone compounds have attracted much attention due to their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b), the author reports herein on the crystal structure of the new title hydrazone compound.

The molecule of the title compound (Fig. 1) exists in a trans conformation with respect to the methylidene unit. The dihedral angle between the (C1–C6) and (C9–C1) benzene rings is 37.6 (3)°.

In the crystal, O–H···O, O–H···N, and N–H···O hydrogen bonds leads to the formation of a three-dimensional network (Table 1, Fig. 2).

Experimental

A mixture of 4-hydroxybenzaldehyde (0.122 g, 1 mmol) and 2-chlorobenzohydrazide (0.171 g, 1 mmol) in 30 ml of methanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Colourless crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a solution of the title compound in methanol.