N′-(2,6-Difluoro­benzyl­idene)pyridine-4-carbohydrazide

Hoong-Kun Fun; Ching Kheng Quah; Divya N Shetty; B Narayana; B K Sarojini

doi:10.1107/S1600536812016716

. 2012 Apr 21;68(Pt 5):o1484. doi: 10.1107/S1600536812016716

N′-(2,6-Difluorobenzylidene)pyridine-4-carbohydrazide

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Divya N Shetty ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3344594 PMID: 22590356

Abstract

In the title compound, C₁₃H₉F₂N₃O, the pyridine ring forms a dihedral angle of 16.92 (7)° with the benzene ring. In the crystal, molecules are linked via N—H⋯O, C—H⋯O and C—H⋯F, with the same O atom accepting two bonds.

Related literature

For related structures, see: Chen (2006 ▶); Nie et al. (2006 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₃H₉F₂N₃O
M _r = 261.23
Monoclinic,
a = 6.8462 (1) Å
b = 24.7903 (5) Å
c = 8.3719 (1) Å
β = 125.249 (1)°
V = 1160.36 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.68 × 0.26 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.923, T _max = 0.988
22044 measured reflections
4531 independent reflections
3819 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.117
S = 1.06
4531 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016716/bv2204sup1.cif

e-68-o1484-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016716/bv2204Isup2.hkl

e-68-o1484-Isup2.hkl^{(222KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016716/bv2204Isup3.cml

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—H1N2⋯O1ⁱ	0.88 (2)	2.00 (2)	2.8554 (12)	163.4 (16)
C1—H1A⋯F1ⁱⁱ	0.93	2.54	3.4622 (13)	169
C7—H7A⋯O1ⁱ	0.93	2.45	3.2253 (13)	141

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

Acknowledgments

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC SAP for financial assistance for the purchase of chemicals. DNS thanks Mangalore University for research facilities.

supplementary crystallographic information

Comment

In view of the importance of isoniazid and its various Schiff base derivatives (Chen, 2006; Nie et al., 2006), the synthesis and crystal structure of the title Schiff base is reported.

In the title molecule (Fig. 1), the pyridine ring (N1/C1-C5) forms a dihedral angle of 16.92 (7)° with the benzene ring (C8-C13). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with related structures (Chen, 2006; Nie et al., 2006).

In the crystal structure, Fig. 2, molecules are linked via intermolecular C1–H1A···F1 and bifurcated N2–H1N2···O1 and C7–H7A···O1 hydrogen bonds (Table 1) into two-dimensional planes parallel to (010).

Experimental

A mixture of isoniazid (1.4 g, 0.01 mol) and 2,6-difluorobenzaldehyde (1.4 ml, 0.01 mol) in 15 ml of absolute alcohol containing 2 drops of hydrochloric acid was refluxed for about 3 h. On cooling, the solid was separated, which was then filtered and recrystallized from DMF. The single crystal was grown from DMF by the slow evaporation method. (m.p. > 523 K).