3-Chloro-N′-(4-diethyl­amino-2-hy­droxy­benzyl­idene)benzohydrazide

Tian-Yi Li; Bing-Bing Li

doi:10.1107/S1600536811001218

. 2011 Jan 15;67(Pt 2):o383. doi: 10.1107/S1600536811001218

3-Chloro-N′-(4-diethylamino-2-hydroxybenzylidene)benzohydrazide

Tian-Yi Li ^a,^*, Bing-Bing Li ^a

PMCID: PMC3051618 PMID: 21523059

Abstract

The asymmetric unit of the title Schiff base compound, C₁₈H₂₀ClN₃O₂, contains two independent molecules. An O—H⋯N hydrogen bond contributes to the planarity of each molecule: the dihedral angles between the two benzene rings are 12.8 (3) and 27.2 (3)° in the two molecules. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For Schiff base compounds, see: Bessy et al. (2006 ▶); Podyachev et al. (2007 ▶); Raj & Kurup (2007 ▶); Pouralimardan et al. (2007 ▶); Bacchi et al. (2006 ▶); Dinda et al. (2002 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For the preparation of the title compound, see: Zhu (2010 ▶).

Experimental

Crystal data

C₁₈H₂₀ClN₃O₂
M _r = 345.82
Triclinic,
a = 10.087 (4) Å
b = 12.939 (5) Å
c = 14.780 (5) Å
α = 78.408 (4)°
β = 80.726 (4)°
γ = 70.632 (4)°
V = 1773.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.951, T _max = 0.955
11600 measured reflections
7423 independent reflections
2683 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.075
wR(F ²) = 0.193
S = 0.91
7423 reflections
445 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001218/om2397sup1.cif

e-67-0o383-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001218/om2397Isup2.hkl

e-67-0o383-Isup2.hkl^{(363.2KB, 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
O1—H1⋯N1	0.82	1.88	2.602 (4)	146
O3—H3⋯N4	0.82	1.91	2.625 (4)	145
N2—H2⋯O4ⁱ	0.90 (6)	2.22 (6)	3.109 (4)	168 (7)
N5—H5⋯O2	0.90 (5)	2.00 (4)	2.899 (4)	176 (7)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

In the last few years, a number of Schiff bases derived from the reaction of aldehydes with benzohydrazides were prepared and structurally characterized (Bessy et al., 2006; Podyachev et al., 2007; Raj & Kurup, 2007; Pouralimardan et al., 2007; Bacchi et al., 2006; Dinda et al., 2002). As a continuation of the work, in the present paper, the title new Schiff base compound, Fig. 1, is reported.

The asymmetric unit of the compound contains two independent Schiff base molecules. In each Schiff base molecule, there is an O—H···N hydrogen bond, which contributes to the planarity of the molecule. The dihedral angles between the two benzene rings in both molecules are 12.8 (3) and 27.2 (3)°, respectively. All the bond lengths are within normal values (Allen et al., 1987). The molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form chains along the a axis (Fig. 2).

Experimental

The compound was prepared and crystallized according to the literature method (Zhu, 2010). 4-Diethylamino-2-hydroxybenzaldehyde (0.193 g, 1 mmol) and 3-chlorobenzohydrazide (0.171 g, 1 mmol) were dissolved in 30 ml absolute methanol. The mixture was stirred at reflux for 10 min, and cooled to room temperature. The clear colorless solution was left to slowly evaporate in air for a few days, yielding colorless block-shaped crystals, which were collected by filtration and washed with methanol.