3-Chloro-N′-[(2-hy­droxy­naphthalen-1-yl)methyl­idene]benzohydrazide

Tian-Yi Li; Wei Li

doi:10.1107/S1600536811000912

. 2011 Jan 12;67(Pt 2):o373. doi: 10.1107/S1600536811000912

3-Chloro-N′-[(2-hydroxynaphthalen-1-yl)methylidene]benzohydrazide

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

PMCID: PMC3051679 PMID: 21523050

Abstract

The title compound, C₁₈H₁₃ClN₂O₂, was prepared by the reaction of 2-hydroxy-1-naphthaldehyde with 3-chlorobenzohydrazide in methanol. An intramolecular O—H⋯N hydrogen bond influences the molecular conformation; the benzene ring and naphthyl ring system form a dihedral angle of 17.1 (3)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains propagated in [101].

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 details of the synthesis, see: Zhu (2010 ▶).

Experimental

Crystal data

C₁₈H₁₃ClN₂O₂
M _r = 324.75
Monoclinic,
a = 7.158 (2) Å
b = 30.886 (3) Å
c = 7.3733 (12) Å
β = 108.924 (2)°
V = 1541.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.950, T _max = 0.955
8306 measured reflections
3288 independent reflections
1635 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.082
wR(F ²) = 0.161
S = 1.04
3288 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.35 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/S1600536811000912/cv5033sup1.cif

e-67-0o373-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000912/cv5033Isup2.hkl

e-67-0o373-Isup2.hkl^{(161.3KB, 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
N2—H2⋯O2ⁱ	0.90 (3)	1.99 (2)	2.860 (4)	162 (4)
O1—H1⋯N1	0.82	1.85	2.574 (4)	146

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

In the last 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 contribution to this work, we present here the title new Schiff base compound (Fig. 1).

There is an intramolecular O—H···N hydrogen bond in the molecule, which influences the molecular conformation - the dihedral angle between the benzene ring and the naphthyl ring is 17.1 (3)°. All the bond lengths are within normal values (Allen et al., 1987). In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in [101] (Fig. 2).

Experimental

The compound was prepared and crystallized according to the literature method (Zhu, 2010). 2-Hydroxy-1-naphthaldehyde (0.172 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 slow evaporation in air for five days, yielding colorless block-shaped crystals, which were collected by filtration and washed with methanol.