(E)-N′-(4-Isopropyl­benzyl­idene)isonicotinohydrazide monohydrate

Mashooq A Bhat; Hatem A Abdel-Aziz; Hazem A Ghabbour; Madhukar Hemamalini; Hoong-Kun Fun

doi:10.1107/S1600536812009099

. 2012 Mar 10;68(Pt 4):o1002. doi: 10.1107/S1600536812009099

(E)-N′-(4-Isopropylbenzylidene)isonicotinohydrazide monohydrate

Mashooq A Bhat ^a, Hatem A Abdel-Aziz ^a, Hazem A Ghabbour ^a, Madhukar Hemamalini ^b, Hoong-Kun Fun ^b,^*,^‡

PMCID: PMC3343969 PMID: 22589878

Abstract

In the title compound, C₁₆H₁₇N₃O·H₂O, the isonicotinohydrazide molecule adopts an E conformation about the central C=N double bond. The dihedral angle between the pyridine and the benzene rings is 54.56 (15)°. In the crystal, molecules are connected via N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For details and the biological activity of isoniazide, see: Bloom & Murray (1992 ▶); Loenhout-Rooyackers & Veen (1998 ▶); Hearn et al. (2009 ▶); Tripathi et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₇N₃O·H₂O
M _r = 285.34
Orthorhombic,
a = 7.7503 (2) Å
b = 11.7894 (3) Å
c = 17.2820 (4) Å
V = 1579.08 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.65 mm⁻¹
T = 296 K
0.89 × 0.19 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.594, T _max = 0.920
6473 measured reflections
2939 independent reflections
2499 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.145
S = 1.04
2939 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 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/S1600536812009099/cv5248sup1.cif

e-68-o1002-sup1.cif^{(25.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009099/cv5248Isup2.hkl

e-68-o1002-Isup2.hkl^{(141.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009099/cv5248Isup3.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—H1N1⋯O1W	0.85	1.90	2.757 (3)	176
O1W—H1W1⋯N1ⁱ	0.85	2.03	2.861 (3)	164
O1W—H2W1⋯O1ⁱⁱ	0.84	2.00	2.779 (3)	154

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

Acknowledgments

MAB, HAA and HAG thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. MH and HFK thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

In the last decade, tuberculosis (TB) has reemerged as one of the leading causes of death in the world, reaching nearly three million deaths annually (Bloom & Murray, 1992). Therefore, the search for new drugs for tuberculosis is of the utmost importance. Treatment regimens are based on a long-term and combined chemotherapy. The most used first-choice drug is isoniazid, a bactericidal drug that acts both intracellularly in the macrophages and extracellularly in the necrotic tissue (Loenhout-Rooyackers & Veen, 1998). The derivatives of isoniazid have been found to possess potential tuberculostatic activity (Hearn et al., 2009; Tripathi et al., 2011). Herein, we present the crystal structure of the title compound, (I).

The asymmetric unit of (I) contains one N'-(4-isopropylbenzylidene) isonicotinohydrazide molecule and one water molecule (Fig. 1). The molecule adopts an E configuration about the central C7═N3 double bond. The dihedral angle between the pyridine (N1/C1–C5) and the benzene (C8–C13) rings is 54.56 (15)°. The hydrazine group is twisted slightly, with a C5-C6-N2-N3 torsion angle of -178.9 (2)°.

In the crystal, the molecules are connected via N—H···O, O—H···N and O—H···O hydrogen bonds (Table 1), forming a three-dimensional networks (Fig. 2).

Experimental

The title compound was prepared by the reaction of 4-isopropyl benzaldehyde (0.15 g, 1 mmol) with isoniazid (0.14 g, 1 mmol) in EtOH (25 mL). After stirring for 3 h, at room temperature, the resulting mixture was concentrated. The precipitate was washed with EtOH to afford the title compound. Colourless blocks of the title compound suitable for X-ray structure determination were recrystallized from EtOH by the slow evaporation of the solvent at room temperature.