(E)-N′-(2,3,4-Trihy­droxy­benzyl­idene)­isonicotinohydrazide dihydrate

H S Naveenkumar; Amirin Sadikun; Pazilah Ibrahim; Jia Hao Goh; Hoong-Kun Fun

doi:10.1107/S1600536810043965

. 2010 Oct 31;66(Pt 11):o3017–o3018. doi: 10.1107/S1600536810043965

(E)-N′-(2,3,4-Trihydroxybenzylidene)isonicotinohydrazide dihydrate

H S Naveenkumar ^a, Amirin Sadikun ^a,^‡, Pazilah Ibrahim ^a, Jia Hao Goh ^b,^§, Hoong-Kun Fun ^b,^*,^¶

PMCID: PMC3009032 PMID: 21589176

Abstract

In the title isoniazid derivative, C₁₃H₁₁N₃O₄·2H₂O, the Schiff base molecule exists in an E configuration with respect to the acyclic C=N bond. An intramolecular O—H⋯N hydrogen bond forms a six-membered ring, producing an S(6) ring motif. The essentially planar pyridine ring [maximum deviation = 0.0119 (8) Å] is inclined at a dihedral angle of 7.30 (4)° with respect to the benzene ring. In the crystal, intermolecular O—H⋯N, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds link the molecules into two-dimensional arrays lying parallel to the (10 Inline graphic ) plane. These arrays are further interconnected into a three-dimensional extended network via O—H⋯O and C—H⋯O hydrogen bonds. A weak intermolecular π–π interaction [centroid-to-centroid distance = 3.5627 (5) Å] is also observed.

Related literature

For general background to and applications of the title isoniazid derivative, see: Janin (2007 ▶); Kahwa et al. (1986 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶). For the preparation of the title compound, see: Lourenço et al. (2008 ▶). For closely related isoniazid structures, see: Naveenkumar et al. (2009 ▶, 2010a ▶,b ▶,c ▶); Shi (2005 ▶). For hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₃H₁₁N₃O₄·2H₂O
M _r = 309.28
Monoclinic,
a = 6.9504 (5) Å
b = 19.9077 (13) Å
c = 10.0930 (7) Å
β = 106.416 (2)°
V = 1339.60 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.35 × 0.18 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.959, T _max = 0.989
21520 measured reflections
5656 independent reflections
4668 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.113
S = 1.03
5656 reflections
259 parameters
All H-atom parameters refined
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.26 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/S1600536810043965/rz2508sup1.cif

e-66-o3017-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043965/rz2508Isup2.hkl

e-66-o3017-Isup2.hkl^{(276.9KB, 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
O2—H1O2⋯N3	0.883 (18)	1.854 (18)	2.6561 (9)	150.1 (16)
O3—H1O3⋯N1ⁱ	0.869 (19)	1.835 (19)	2.6911 (10)	168.4 (18)
O4—H1O4⋯O1W	0.895 (18)	1.769 (18)	2.6559 (9)	170.5 (18)
N2—H1N2⋯O2Wⁱⁱ	0.890 (16)	2.132 (15)	2.9910 (9)	162.1 (14)
O1W—H1W1⋯O1ⁱⁱⁱ	0.926 (18)	1.880 (18)	2.7834 (9)	164.6 (16)
O1W—H2W1⋯O2W	0.837 (19)	2.077 (18)	2.8980 (11)	167.0 (18)
O2W—H1W2⋯O2^iv	0.831 (15)	2.161 (15)	2.9570 (11)	160.3 (14)
O2W—H2W2⋯O4^v	0.86 (2)	1.91 (2)	2.7688 (9)	173.3 (19)
C4—H4A⋯O1^vi	0.922 (14)	2.575 (14)	3.2930 (11)	135.1 (11)
C7—H7A⋯O2Wⁱⁱ	0.988 (14)	2.347 (14)	3.2176 (10)	146.7 (12)

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

Acknowledgments

This research was supported by Universiti Sains Malaysia (USM) under a University Research Grant (No. 1001/PFARMASI/815005). JHG and HKF thank USM for a Research University Grant (No. 1001/PFIZIK/811160). HSNK is grateful to USM for a USM Fellowship.

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). Schiff bases have attracted much attention because of their biological activity (Kahwa et al., 1986). As a part of our current work on synthesis of (E)-N'-substituted isonicotinohydrazide derivatives, in this paper we present the crystal structure of the title compound.

The title isoniazid derivative comprises of a (E)-N'-(2,3,4-trihydroxybenzylidene)isonicotinohydrazide molecule and two water molecules of crystallization (Fig. 1). The Schiff base molecule exists in an E configuration with respect to the acyclic C7═N3 bond [C7═N3 = 1.2921 (10) Å; torsion angle N2—N3—C7—C8 = 178.85 (7)°]. An intramolecular O2—H1O2···N3 hydrogen bond (Table 1) generates a six-membered ring, producing an S(6) ring motifs (Bernstein et al., 1995). The pyridine ring with atom sequence C1/C2/N1/C3/C4/C5 is essentially planar, with a maximum deviation of 0.0119 (8) Å at atom C5. There is a slight inclination between the pyridine and benzene rings, as indicated by the dihedral angle formed of 7.30 (4)°. All bond lengths and angles are consistent to those observed in closely related isoniazid structures (Naveenkumar et al., 2009, 2010a,b,c; Shi, 2005).

In the crystal packing, water molecules play an extensive part in forming the hydrogen-bonded structure. Neighbouring molecules are linked into two-dimensional arrays parallel to the (101) plane (Fig. 2) by intermolecular O3—H1O3···N1, O4—H1O4···O1W, N2—H1N2···O2W, O1W—H1W1···O1, O2W—H2W2···O4 and C7—H7A···O2W hydrogen bonds (Table 1). These arrays are further interconnected by intermolecular O1W—H2W1···O2W, O2W—H1W2···O2 and C4—H4A···O1 hydrogen bonds (Table 1) into a three-dimensional extended structure (Fig. 3). Weak intermolecular π–π aromatic stacking interactions involving the pyridine and benzene rings [Cg1···Cg2 = 3.5627 (5) Å, symmetry code: -x + 2, -y + 1, -z + 2] stabilizing the crystal structure.

Experimental

The isoniazid derivative was prepared following the procedure by Lourenço et al., 2008. The title compound was prepared by the reaction between 2,3,4-trihydroxybenzaldehyde (1.0 eq) with 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, purified by washing with cold ethanol and ethyl ether, afforded the pure derivative. The brown-coloured single crystals suitable for X-ray analysis were obtained by recrystallization with ethanol.