N′-(2-Meth­oxy-1-naphthyl­idene)nicotino­hydrazide

Cong Li; Ping Wang; Yong-Qing Su

doi:10.1107/S1600536810003843

. 2010 Feb 6;66(Pt 3):o520. doi: 10.1107/S1600536810003843

N′-(2-Methoxy-1-naphthylidene)nicotinohydrazide

Cong Li ^a, Ping Wang ^a, Yong-Qing Su ^a,^*

PMCID: PMC2983545 PMID: 21580294

Abstract

The title compound, C₁₈H₁₅N₃O₂, was prepared by the reaction of 2-methoxynaphthaldehyde with nicotinic acid hydrazide in methanol. The dihedral angle between the naphthalene ring system and the pyridine ring is 9.2 (3)°. An intramolecular C—H⋯N hydrogen bond is observed. In the crystal structure, molecules are linked into chains running along the c axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For general background to Schiff base compounds, see: Archibald et al. (1994 ▶); Harada et al. (1999 ▶); Ogawa et al. (1998 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Sun et al. (2009 ▶); Wen et al. (2009 ▶).

Experimental

Crystal data

C₁₈H₁₅N₃O₂
M _r = 305.33
Tetragonal,
a = 9.6163 (13) Å
c = 17.442 (3) Å
V = 1612.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.981, T _max = 0.983
8478 measured reflections
1498 independent reflections
1109 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.099
S = 1.03
1498 reflections
212 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 global, I. DOI: 10.1107/S1600536810003843/ci5027sup1.cif

e-66-0o520-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003843/ci5027Isup2.hkl

e-66-0o520-Isup2.hkl^{(73.9KB, 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 (1)	2.00 (2)	2.833 (3)	154 (3)
C9—H9⋯N1	0.93	2.30	2.930 (5)	125

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge support by the Science and Technology Department of Yunnan Province, the Program of Yunnan Province’s Young-Middle Aged Reserve Scientific and Technological Principal Culture Plan (grant No. 2006PY01–50) and the fund of Yunnan Province’s Applied Research Plan (grant No. 2006E0032M).

supplementary crystallographic information

Comment

Schiff bases have been received much attention in recent years (Ogawa et al., 1998; Archibald et al., 1994; Harada et al., 1999). As a further investigation of the structures of Schiff base compounds, the title new compound is reported here.

In the title compound, the dihedral angle between the naphthalene ring system and the pyridine ring is 9.2 (3)°. The bond lengths are comparable to those observed in related Schiff base compounds (Wen et al., 2009; Mohd Lair et al., 2009; Sun et al., 2009).

In the crystal structure, molecules form chains running along the c axis through intermolecular N—H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

2-Methoxynaphthaldehyde (1.0 mmol, 186 mg) and nicotinic acid hydrazide (1.0 mmol, 137 mg) were dissolved in methanol (30 ml). The mixture was stirred at room temperature for 1 h to give a colourless solution. After keeping the solution in air for 5 d, colourless block shaped crystals were formed.