(E)-N′-(2,4,5-Trimethoxy­benzyl­idene)isonicotinohydrazide dihydrate

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

doi:10.1107/S1600536810015254

. 2010 Apr 30;66(Pt 5):o1235–o1236. doi: 10.1107/S1600536810015254

(E)-N′-(2,4,5-Trimethoxybenzylidene)isonicotinohydrazide dihydrate

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

PMCID: PMC2979138 PMID: 21579256

Abstract

The asymmetric unit of the title compound, C₁₆H₁₇N₃O₄·2H₂O, contains one Schiff base molecule and two water molecules. The Schiff base molecule exists in an E configuration with respect to the C=N double bond and is essentially planar, the dihedral angle between the benzene and pyridine rings being 5.48 (8)°. The three methoxy groups are also coplanar with the benzene ring [C—O—C—C torsion angles = 3.9 (2), 178.51 (15) and 0.8 (2) Å]. In the crystal structure, the water molecules link the molecules into a three-dimensional network via intermolecular N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For applications of isoniazid 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 ▶, 2010a ▶,b ▶); Shi (2005 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₇N₃O₄·2H₂O
M _r = 351.36
Monoclinic,
a = 6.8156 (4) Å
b = 14.5648 (10) Å
c = 8.5589 (5) Å
β = 103.421 (2)°
V = 826.42 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.50 × 0.28 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.947, T _max = 0.979
10676 measured reflections
2254 independent reflections
2171 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.126
S = 1.17
2254 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.56 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/S1600536810015254/kj2145sup1.cif

e-66-o1235-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015254/kj2145Isup2.hkl

e-66-o1235-Isup2.hkl^{(110.8KB, 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⋯O2W	0.88 (3)	2.05 (3)	2.916 (2)	171 (2)
O2W—H1W2⋯O1W	0.84	1.93	2.748 (2)	167
O2W—H2W2⋯N1ⁱ	0.83	2.10	2.887 (2)	158
O1W—H1W1⋯O3ⁱⁱ	0.85	2.18	2.8913 (19)	141
O1W—H1W1⋯O4ⁱⁱ	0.85	2.43	3.204 (2)	152
O1W—H2W1⋯O1ⁱⁱⁱ	0.86	1.99	2.834 (2)	170
C4—H4A⋯O2W	0.93	2.34	3.253 (3)	169
C7—H7A⋯O2W	0.93	2.58	3.375 (2)	143
C14—H14A⋯O4ⁱⁱⁱ	0.96	2.60	3.281 (2)	128

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

Acknowledgments

This research was supported by Universiti Sains Malaysia (USM) under the Fundamental Research Grant Scheme (203/PFARMASI/671157). HSNK and CSY are grateful to USM for USM fellowships. HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012).

supplementary crystallographic information

Comment

In the search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden & Barry, 2000). As a part of a current work of synthesis of such derivatives, in this paper we present the crystal structure of the title compound which was synthesized in our lab.

The asymmetric unit consists of one Schiff base molecule and two water molecules (Fig. 1). The geometry parameters are comparable to those related structures (Naveenkumar et al., 2009, 2010a, b; Shi, 2005). The molecule exists in an E configuration with respect to the C7═N3 double bond. The molecule is essentially coplanar with dihedral angle between the benzene ring and the pyridine ring being 5.48 (8)°. The three methoxy groups are coplanar with the benzene ring [torsion angle, C14–O2–C9–C10 = 3.9 (2), C15–O3–C11–C12 = 178.51 (15), C16–O4–C12–C13 = 0.8 (2) Å]. In the crystal structure, the water molecules link the molecules into a three-dimensional network by the 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 the procedure by Lourenco et al., (2008). The title compound was prepared by reaction between 2, 4, 5-trimethoxybenzaldehyde (1.0 eq) and isoniazid (1.0 eq) in ethanol/water. After stirring for 1-3 hours at room temperature, the resulting mixture was concentrated under reduced pressure. The residue, purified by washing with cold ethanol and ethyl ether, afforded the pure derivative. The yellow single crystal suitable for X-ray analysis was obtained by recrystalization with methanol.