N′-(5-Chloro-2-hydroxy­benzyl­idene)nicotinohydrazide

Chong-Gui Ren

doi:10.1107/S1600536809020819

. 2009 Jun 6;65(Pt 7):o1505–o1506. doi: 10.1107/S1600536809020819

N′-(5-Chloro-2-hydroxybenzylidene)nicotinohydrazide

Chong-Gui Ren ^a,^*

PMCID: PMC2969359 PMID: 21582803

Abstract

There are two independent Schiff base molecules in the asymmetric unit of the title compound, C₁₃H₁₀ClN₃O₂. The dihedral angles between the benzene and pyridine rings are 12.8 (2) and 1.9 (2)° in the two molecules. Intramolecular O—H⋯N hydrogen bonds are observed. Molecules are linked into centrosymmetric R ⁴ ₄(26) motifs by N—H⋯O and N—H⋯N interactions.

Related literature

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999 ▶); Ren et al. (2002 ▶); Eltayeb et al. (2008 ▶); Sinha et al. (2008 ▶). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008 ▶); Prabhakaran et al. (2006 ▶); Dhar et al. (2005 ▶). For related structures, see: Cui et al. (2007 ▶); Jing et al. (2007 ▶); Ma et al. (2008 ▶); Salhin et al. (2007 ▶); Lin et al. (2007 ▶); Alhadi et al. (2008 ▶); Xue et al. (2008 ▶); Wang et al. (2008 ▶); Lu (2008 ▶); Diao et al. (2008 ▶); Qiu (2009 ▶); Mohd Lair et al. (2009a ▶,b ▶). For reference structural data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₁₀ClN₃O₂
M _r = 275.69
Monoclinic,
a = 9.792 (2) Å
b = 23.358 (3) Å
c = 10.926 (2) Å
β = 96.848 (2)°
V = 2481.2 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.30 × 0.30 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.913, T _max = 0.921
14387 measured reflections
5342 independent reflections
3193 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.115
S = 1.01
5342 reflections
351 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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/S1600536809020819/bx2215sup1.cif

e-65-o1505-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020819/bx2215Isup2.hkl

e-65-o1505-Isup2.hkl^{(261.6KB, 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	2.594 (2)	145
O3—H3⋯N4	0.82	1.82	2.538 (2)	146
N5—H5⋯N3ⁱ	0.891 (10)	2.109 (11)	2.991 (3)	171 (2)
N2—H2⋯O3	0.892 (10)	2.097 (10)	2.984 (2)	173 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges Zaozhuang University for funding this study.

supplementary crystallographic information

Comment

The Schiff base compounds show excellent biological properties (Jeewoth et al., 1999; Ren et al., 2002; Eltayeb et al., 2008; Sinha et al., 2008). Moreover, the Schiff base compounds have been widely used as versatile ligands in coordination chemistry (Shivakumar et al., 2008; Prabhakaran et al., 2006; Dhar et al., 2005). We report here the crystal structure of the title compound .In the title compound, Fig. 1, there two independent molecules in the symmetric unit.The dihedral angles between the benzene and pyridine rings are 12.8 (2) and 1.9 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987) and comparable to those in other similar compounds (Cui et al., 2007; Jing et al., 2007; Ma et al., 2008; Salhin et al., 2007; Lin et al., 2007; Alhadi et al., 2008; Xue et al., 2008; Wang et al., 2008; Lu, 2008; Diao et al., 2008; Qiu, 2009; Lair et al., 2009a,b). The molecules of the title compound are linked into centrosymmetric R⁴₄(26) motifs by N–H···O and N–H···N interactions (Table 1, Fig. 2) (Bernstein et al., 1995).

Experimental

All the starting materials were obtained with AR grade from Lancaster. 5-Chloro-2-hydroxybenzaldehyde (1.0 mmol, 157.1 mg) and nicotinohydrazide (1.0 mmol, 137.1 mg) were refluxed in a 30 ml methanol solution for 30 min to give a clear yellow solution. Yellow block-shaped single crystals of the compound were obtained by slow evaporation of the solution for five days at room temperature.