6-Chloro-N′-(2-hydr­oxy-1-naphthyl­methyl­ene)nicotinohydrazide

Feng Zhi

doi:10.1107/S1600536807063611

. 2007 Dec 6;64(Pt 1):o150. doi: 10.1107/S1600536807063611

6-Chloro-N′-(2-hydroxy-1-naphthylmethylene)nicotinohydrazide

Feng Zhi ^a,^*

PMCID: PMC2915218 PMID: 21200715

Abstract

The title compound, C₁₇H₁₂ClN₃O₂, was synthesized by the Schiff base condensation reaction of 2-hydroxy-1-naphthaldehyde with 6-chloronicotinic acid hydrazide in a methanol solution. The molecule displays a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the naphthyl ring system and the pyridine ring is 7.6 (4)°. There is an intramolecular O—H⋯N hydrogen bond. The crystal structure is stabilized by intermolecular N—H⋯O and C—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For related literature, see: Allen et al. (1987 ▶); Chen et al. (1997 ▶); Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C₁₇H₁₂ClN₃O₂
M _r = 325.75
Monoclinic,
a = 4.7450 (9) Å
b = 6.0420 (12) Å
c = 25.752 (5) Å
β = 91.93 (3)°
V = 737.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 (2) K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.937, T _max = 0.940
5692 measured reflections
2980 independent reflections
1948 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.110
S = 0.99
2980 reflections
212 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ▶), 1447 Friedel pairs
Flack parameter: 0.11 (10)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063611/bv2083sup1.cif

e-64-0o150-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063611/bv2083Isup2.hkl

e-64-0o150-Isup2.hkl^{(146.2KB, 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
O2—H2⋯N3	0.82	1.84	2.559 (4)	146
N2—H2B⋯O1ⁱ	0.900 (10)	2.05 (2)	2.862 (4)	150 (4)
C2—H2A⋯O1ⁱⁱ	0.93	2.50	3.396 (4)	161

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

Acknowledgments

Financial support from the Third Affiliated Hospital of Suzhou University is acknowledged.

supplementary crystallographic information

Comment

Schiff base compounds have been widely investigated over a century (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). In this paper, the crystal structure of a new Schiff base compound derived from the condensation reaction of 2-hydroxy-1-naphthaldehyde with 6-chloronicotinic acid hydrazide is reported.

The Schiff base molecule of the compound displays a trans configuration with respect to the C?N and C—N bonds (Fig. 1). The dihedral angle between the C8—C17 naphthyl ring and the C1—C5/N1 pyridine ring is 7.6 (4)°. All the bond lengths are within normal ranges (Allen et al., 1987). There is an intramolecular O–H···N hydrogen bond in the molecule (Table 1). The crystal structure is stabilized by intermolecular N–H···O and C–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

Experimental

2-Hydroxy-1-naphthaldehyde (0.1 mmol, 17.2 mg) and 6-chloronicotinic acid hydrazide (0.1 mmol, 17.1 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature to give a clear yellow solution. Crystals of the title compound were formed by gradual evaporation of the solvent for two days at room temperature.