N′-(2-Furylmethyl­ene)nicotinohydrazide

Heng-yu Qian; Zhi-gang Yin; Chun-xia Zhang; Zhi-qiang Yao

doi:10.1107/S1600536809033698

. 2009 Aug 29;65(Pt 9):o2260. doi: 10.1107/S1600536809033698

N′-(2-Furylmethylene)nicotinohydrazide

Heng-yu Qian ^a, Zhi-gang Yin ^a,^*, Chun-xia Zhang ^a, Zhi-qiang Yao ^a

PMCID: PMC2970065 PMID: 21577656

Abstract

The asymmetric unit of the title compound, C₁₁H₉N₃O₂, contains two independent molecules: the dihedral angles between the pyridine ring and the furyl ring are 17.00 (16) and 34.12 (15)°. The crystal structure involves intermolecular C—H⋯O, N—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For the role played by Schiff bases in the development of various proteins and enzymes, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶).

Experimental

Crystal data

C₁₁H₉N₃O₂
M _r = 215.21
Monoclinic,
a = 17.4363 (3) Å
b = 16.9143 (3) Å
c = 7.9639 (1) Å
β = 115.326 (1)°
V = 2122.99 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.34 × 0.24 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.964, T _max = 0.981
9336 measured reflections
2443 independent reflections
1908 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.086
S = 1.06
2443 reflections
290 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536809033698/hg2558sup1.cif

e-65-o2260-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033698/hg2558Isup2.hkl

e-65-o2260-Isup2.hkl^{(120KB, 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⋯O4ⁱ	0.86	2.26	3.080 (2)	161
N2—H2A⋯N4ⁱ	0.86	2.51	3.112 (3)	128
N5—H5A⋯O2ⁱⁱ	0.86	2.01	2.843 (3)	162
C8—H8A⋯O4ⁱ	0.93	2.56	3.433 (3)	156
C16—H16A⋯O2ⁱⁱ	0.93	2.45	3.228 (3)	141
C22—H22A⋯O2ⁱⁱ	0.93	2.43	3.260 (3)	149

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

Acknowledgments

The authors would like to express their deep appreciation to the Startup Fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry (No.2005001) and the Fund for Natural Scientific Research of Zhengzhou University of Light Industry (000455).

supplementary crystallographic information

Comment

The chemistry of Schiff bases has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our in the study of the coordination chemistry of Schiff bases, we synthesized the title compound and determined its crystal structure.

The molecular structure is shown in Fig.1. Each molecule is not planar, making the dihedral angle of 17.00 (16) and 34.12 (15)° between pyridine and furyl rings, respectively. In the crystal structure, molecules are linked through intermolecular C—H···O, N—H···N and N—H···O hydrogen bonds, forming a network.

Experimental

Pyridine-4-carboxylic acid hydrazide (1 mmol, 0.137 g) was dissolved in anhydrous ethanol (15 ml), The mixture was stirred for several minutes at 351 K. Furan-2-carbaldehyde (1 mmol, 0.96 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol. Pink single crystals of (I) was obtained after 3 d.