2-Hydr­oxy-N′-(2-methoxy­naphthyl­idene)benzohydrazide

Xiao-Yang Qiu

doi:10.1107/S1600536808026962

. 2008 Aug 23;64(Pt 9):o1829–o1830. doi: 10.1107/S1600536808026962

2-Hydroxy-N′-(2-methoxynaphthylidene)benzohydrazide

Xiao-Yang Qiu ^a,^*

PMCID: PMC2960698 PMID: 21201804

Abstract

The title Schiff base compound, C₁₉H₁₆N₂O₃, prepared by the reaction of 2-methoxy-1-naphthylaldehyde and 2-hydroxybenzohydrazide, crystallizes with two independent molecules in the asymmetric unit. Each molecule exists in a trans configuration with respect to the methylidene group. The naphthyl ring system make dihedral angles of 65.0 (2)° and 55.8 (2)° with the planes of the benzene rings. Intramolecular N—H⋯O and O—H⋯O hydrogen bonds help to stabilize the molecular conformations. In the crystal structure, molecules are linked into one-dimensional chains parallel to the c axis by intermolecular O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For the biological properties of hydrazones, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Fun et al. (2008 ▶). For our previous reports on hydrazones, see: Qiu, Fang et al. (2006 ▶); Qiu, Luo et al. (2006a ▶,b ▶); Qiu, Xu et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Singh et al. (2007 ▶); Narayana et al. (2007 ▶); Cui et al. (2007 ▶); Diao et al. (2008 ▶).

Experimental

Crystal data

C₁₉H₁₆N₂O₃
M _r = 320.34
Monoclinic,
a = 15.186 (3) Å
b = 9.059 (2) Å
c = 24.135 (3) Å
β = 108.331 (3)°
V = 3151.8 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.10 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.991, T _max = 0.994
17807 measured reflections
6805 independent reflections
4792 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.120
S = 1.03
6805 reflections
443 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536808026962/at2612sup1.cif

e-64-o1829-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026962/at2612Isup2.hkl

e-64-o1829-Isup2.hkl^{(333KB, 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
O3—H3⋯N3ⁱ	0.82	2.24	3.0049 (18)	155
O3—H3⋯O5ⁱ	0.82	2.30	2.914 (2)	133
O6—H6⋯O2	0.82	1.87	2.6683 (17)	164
N2—H2⋯O3	0.918 (19)	1.942 (16)	2.6518 (18)	132.7 (17)
N4—H4A⋯O6	0.895 (9)	1.948 (16)	2.6581 (19)	135.0 (18)
N4—H4A⋯O4	0.895 (9)	2.38 (2)	2.877 (2)	114.9 (16)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges the Education Office of Anhui Province (project No. KJ2008B178).

supplementary crystallographic information

Comment

Hyrazone compounds, which derived from the reaction of aldehydes with hydrazides, have been widely studied due to their excellent biological properties (Bedia et al., 2006; Rollas et al., 2002; Fun et al., 2008). Recently, we have reported a few Schiff hydrazone compounds (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006a,b; Qiu, Xu et al., 2006), we report herein the crystal structure of the title new compound, (I).

Compound (I) crystallizes with two independent molecules in the asymmetric unit (Fig. 1). Each molecule exists in a trans configuration with respect to the methylidene group. The naphthyl rings make dihedral angles of 65.0 (2)° and 55.8 (2)° with the planes of the benzene rings. The bond lengths and angles in (I) are found to have normal values (Allen et al., 1987) and comparable to the values in the similar compounds (Singh et al., 2007; Narayana et al., 2007; Cui et al., 2007; Diao et al., 2008). Intramolecular O–H···O and N–H···O hydrogen bonds (Table 1) help to stabilize the molecular conformations. In the crystal structure, molecules are linked into one-dimensional chains parallel to the c axis by intermolecular O–H···N and O–H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

The title compound was prepared by the Schiff base condensation of equimolar (0.5 mmol each) 2-methoxy-1-naphthylaldehyde and 2-hydroxybenzohydrazide in methanol (20 ml). Excess methanol was removed from the reaction mixture with distillation. The colourless solid was filtered and dried in air. Colourless block-shaped crystals suitable for X-ray diffraction were obtained from a methanol solution.