(E)-N′-[(E)-3-(4-Hydr­oxy-3-methoxy­phen­yl)allyl­idene]isonicotinohydrazide

H S Naveenkumar; Amirin Sadikun; Pazilah Ibrahim; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S1600536810000371

. 2010 Jan 9;66(Pt 2):o291. doi: 10.1107/S1600536810000371

(E)-N′-[(E)-3-(4-Hydroxy-3-methoxyphenyl)allylidene]isonicotinohydrazide

H S Naveenkumar ^a, Amirin Sadikun ^a,^‡, Pazilah Ibrahim ^a, Ching Kheng Quah ^b,^§, Hoong-Kun Fun ^b,^*,^¶

PMCID: PMC2979869 PMID: 21579726

Abstract

In the title compound, C₁₆H₁₅N₃O₃, the dihedral angle between the pyridine and benzene rings is 7.66 (5)°. The crystal packing is consolidated by intermolecular C—H⋯O and O—H⋯N interactions, which link the molecules into zigzag chains propagating along [010]. The chains are further linked into a three-dimensional network by N—H⋯O, C—H⋯N, C—H⋯O and C—H⋯π interactions.

Related literature

For the synthesis, see: Lourenco et al. (2008 ▶). For the tuberculostatic activities of isoniazid derivatives, see: Janin (2007 ▶). For related structures, see: Naveenkumar et al. (2009a ▶,b ▶,c ▶); Shi (2005 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₅N₃O₃
M _r = 297.31
Monoclinic,
a = 5.0470 (1) Å
b = 28.9314 (6) Å
c = 9.6446 (2) Å
β = 90.010 (1)°
V = 1408.27 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.53 × 0.20 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.950, T _max = 0.992
33857 measured reflections
4144 independent reflections
3534 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.110
S = 1.05
4144 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 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/S1600536810000371/hb5304sup1.cif

e-66-0o291-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000371/hb5304Isup2.hkl

e-66-0o291-Isup2.hkl^{(203.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C10–C15 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.886 (15)	1.999 (15)	2.8622 (12)	164.4 (14)
O2—H1O2⋯N1ⁱⁱ	0.87 (2)	1.96 (2)	2.7750 (13)	156.9 (19)
C2—H2A⋯O3ⁱⁱⁱ	0.93	2.55	3.1651 (14)	124
C4—H4A⋯N3^iv	0.93	2.60	3.4747 (14)	156
C7—H7A⋯O1ⁱ	0.93	2.52	3.2405 (14)	135
C16—H16B⋯Cg1^v	0.96	2.65	3.4556 (12)	142

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

Acknowledgments

This research was supported by Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815005). HKF and CKQ thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). HSNK and CKQ are grateful financial assistance through a USM fellowship.

supplementary crystallographic information

Comment

In the search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activities (e.g. Janin, 2007). As a part of a current work of synthesis of (E)-N'-substituted isonicotinohydrazide derivatives, we present the crystal structure of the title compound, (I), (Fig. 1).

The pyridine ring (N1/C1–C5) in (I) forms dihedral angle of 7.66 (5)° with the benzene ring (C10–C15), indicating that they are almost co-planar to each other. Bond lengths and angles are within normal ranges, and comparable to closely related structures (Naveenkumar et al., 2009a,b,c; Shi, 2005).

The crystal packing is consolidated by intermolecular C2—H2A···O3 and O2—H1O2···N1 interactions (Fig. 2) which link the independent molecules into zig-zag chains along the [0 1 0] direction. The crystal structure is further linked via N2—H1N2···O1, C4—H4A···N3 and C7—H7A···O1 interactions, into three-dimensional network. The structure is also stabilized by C—H···π interactions (Table 1).

Experimental

The isoniazid derivative was prepared following the procedure by Lourenco et al. (2008). (E)-N'-[(E)-3-(4-hydroxy-3-methoxyphenyl) allylidene]isonicotinohydrazide was prepared by reaction between the 4-hydroxy-3-methoxy cinnamaldehyde (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. Yellow needles of (I) were obtained by recrystallization from methanol.