N′-(3-Phenyl­allyl­idene)isonicotino­hydrazide

Feng-Yu Bao

doi:10.1107/S1600536808026287

. 2008 Aug 20;64(Pt 9):o1789. doi: 10.1107/S1600536808026287

N′-(3-Phenylallylidene)isonicotinohydrazide

Feng-Yu Bao ^a,^*

PMCID: PMC2960596 PMID: 21201769

Abstract

The asymmetric unit of the title compound, C₁₅H₁₃N₃O, contains two similar molecules. Each molecule is non-planar, as indicated by the dihedral angles between the pyridine and benzene rings of 45.2 (2) and 56.6 (2)°. The crystal structure is consolidated by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Kahwa et al. (1986 ▶); Qian et al. (2006 ▶); Santos et al. (2001 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O
M _r = 251.28
Monoclinic,
a = 12.608 (8) Å
b = 11.023 (7) Å
c = 10.044 (7) Å
β = 105.94 (3)°
V = 1342.2 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.98, T _max = 0.98
11645 measured reflections
3110 independent reflections
2784 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.134
S = 1.01
3110 reflections
349 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 ▶); 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/S1600536808026287/ez2136sup1.cif

e-64-o1789-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026287/ez2136Isup2.hkl

e-64-o1789-Isup2.hkl^{(152.6KB, 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
N2—H2A⋯O2ⁱ	0.86 (5)	2.19 (5)	3.050 (6)	174 (3)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Interest in the chemistry of Schiff bases has increased considerably in recent years, mainly due to their novel properties and their application in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). Structural information of Schiff base derivatives is useful in studying their coordination chemisty. As part of our research, we have synthesized the title compound (I) and report its crystal structure here.

The molecular structure is shown in Fig. 1. Each molecule is non-planar, with dihedral angles of 45.2 (2) and 56.6 (2)° between the pyridine ring and the benzene ring for the two molecules. Bond lengths and angles agree with those found for isonicotinohydrazide derivatives (Qian et al., 2006).

Intermolecular N—H···O hydrogen bonds link pairs of molecules.

Experimental

Pyridine-4-carboxylic acid hydrazide (1 mmol, 0.137 g) was dissolved in anhydrous methanol, whereafter H₂SO₄ (98%, 0.5 ml) was added and the mixture was stirred for several minutes at 351 K. A solution of cinnamaldehyde (1 mmol, 0.132 g) in methanol (8 ml) was then added dropwise and the mixture was stirred under reflux for 2 h. The product was isolated and recrystallized from dichloromethane, brown single crystals of (I) were obtained after 2 d.