(E)-N′-(2,4,5-Trifluorobenzyl­idene)isonicotinohydrazide monohydrate

H S Naveenkumar; Amirin Sadikun; Pazilah Ibrahim; Chin Sing Yeap; Hoong-Kun Fun

doi:10.1107/S1600536810004514

. 2010 Feb 10;66(Pt 3):o579. doi: 10.1107/S1600536810004514

(E)-N′-(2,4,5-Trifluorobenzylidene)isonicotinohydrazide monohydrate

H S Naveenkumar ^a, Amirin Sadikun ^a,^‡, Pazilah Ibrahim ^a, Chin Sing Yeap ^b,^§, Hoong-Kun Fun ^b,^*,^¶

PMCID: PMC2983744 PMID: 21580346

Abstract

In the Schiff base molecule of the title compound, C₁₃H₈F₃N₃O·H₂O, the benzene ring and the pyridine ring are nearly coplanar, making a dihedral angle of 6.64 (7)°. The molecule exists in an E configuration with respect to the C=N double bond. In the crystal structure, molecules are linked via the water molecules into two-dimensional planes parallel to the ab plane through intermolecular N—H⋯O, O—H⋯O O—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For applications of isoniazid (isonicotinylhydrazine) derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶); Kahwa et al. (1986 ▶). For the preparation of the title compound, see: Lourenco et al. (2008 ▶). For related structures, see: Naveenkumar et al. (2009 ▶, 2010 ▶); Shi (2005 ▶).

Experimental

Crystal data

C₁₃H₈F₃N₃O·H₂O
M _r = 297.24
Triclinic,
a = 4.9241 (1) Å
b = 6.3915 (1) Å
c = 21.3387 (2) Å
α = 88.616 (1)°
β = 86.556 (1)°
γ = 76.056 (1)°
V = 650.58 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.32 × 0.32 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.958, T _max = 0.984
14710 measured reflections
4024 independent reflections
2730 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.146
S = 1.05
4024 reflections
230 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 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 datablocks global, I. DOI: 10.1107/S1600536810004514/sj2725sup1.cif

e-66-0o579-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004514/sj2725Isup2.hkl

e-66-0o579-Isup2.hkl^{(197.2KB, 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—H1N2⋯O1W	0.883 (19)	1.921 (19)	2.7910 (13)	168.1 (16)
O1W—H1W1⋯O1ⁱ	0.79 (2)	2.03 (2)	2.8263 (17)	176.3 (18)
O1W—H2W1⋯O1ⁱⁱ	0.84 (2)	2.19 (2)	2.9670 (17)	155 (2)
O1W—H2W1⋯N1ⁱⁱ	0.84 (2)	2.47 (2)	3.1024 (14)	133.7 (19)
C7—H7A⋯O1W	0.967 (13)	2.492 (14)	3.2576 (16)	135.9 (12)
C13—H13A⋯O1W	0.963 (19)	2.427 (18)	3.3308 (19)	156.2 (14)

Open in a new tab

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

Acknowledgments

This research was supported by Universiti Sains Malaysia (USM) under the University Research Grant (1001/PFARMASI/815005). HSNK and CSY each thank USM for the award of a USM Fellowship. HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012).

supplementary crystallographic information

Comment

In the search for new biologically active compounds, isoniazid (isonicotinylhydrazine) derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden & Barry, 2000). As part of our current work on the synthesis of (E)-N'-substituted isonicotinohydrazide derivatives, in this paper we present the crystal structure of the title compound, (I).

The asymmetric unit consists of one Schiff base molecule and one water molecule (Fig. 1). The geometric parameters are comparable to those related structures (Naveenkumar et al., 2009, 2010; Shi, 2005). The molecule is nearly coplanar with a dihedral angle between the benzene ring and the pyridine ring of 6.64 (7)°. The molecule exists in an E configuration with respect to the C7=N1 double bond. In the crystal structure, the water molecules link the molecules into two-dimensional planes parallel to the ab plane through intermolecular N–H···O, O–H···O O–H···N and C–H···O hydrogen bonds (Fig. 2, Table 1).

Experimental

The isoniazid derivative was prepared following a procedure reported by Lourenco et al., (2008). 2,4,5-triflurobenzaldehyde (1.0 eq) was added to isoniazid (1.0 eq) in ethanol/water. After stirring for 1-3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue was purified by washing with cold ethanol and diethyl ether to give the pure derivative. Colourless single crystals suitable for X-ray analysis were obtained by re-crystallization from methanol.