N′-[(1E,2E)-3,7-Dimethyl­octa-2,6-dien-1-yl­idene]pyridine-4-carbohydrazide

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

doi:10.1107/S1600536812009075

. 2012 Mar 24;68(Pt 4):o1144–o1145. doi: 10.1107/S1600536812009075

N′-[(1E,2E)-3,7-Dimethylocta-2,6-dien-1-ylidene]pyridine-4-carbohydrazide

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

PMCID: PMC3344089 PMID: 22606092

Abstract

In the title compound, C₁₆H₂₁N₃O, the molecule adopts an E conformation about the central C=N double bond. The 2-methylpent-2-ene group is disordered over two sets of sites, with a refined occupancy ratio of 0.785 (8):0.215 (8). The dihedral angle between the essentially planar [the r.m.s. value for the major component is 0.021 (7) and its maximum deviation is 0.025 (4) Å; the r.m.s. value for the minor component is 0.03 (4) and its maximum deviation is 0.05 (3) Å] major and minor components of the 2-methylbut-2-ene group is 35.9 (13)°. In the crystal, C—H⋯O and N—H⋯O hydrogen bonds link the molecules, with the same O atom acting as the acceptor. This results in C ¹ ₁(4) and C ¹ ₁(5) [001] chains.

Related literature

For details and the biological activity of isoniazide, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶); Hearn et al. (2009 ▶); Tripathi et al. (2011 ▶). For related structures, see: Naveenkumar et al. (2010) ▶; Jiang et al. (2009 ▶); Khan et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₂₁N₃O
M _r = 271.36
Monoclinic,
a = 17.5415 (8) Å
b = 12.0708 (6) Å
c = 7.8430 (4) Å
β = 101.854 (3)°
V = 1625.26 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.56 mm⁻¹
T = 296 K
0.90 × 0.27 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.633, T _max = 0.912
16548 measured reflections
2978 independent reflections
2376 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.154
S = 1.03
2978 reflections
239 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 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/S1600536812009075/lh5421sup1.cif

e-68-o1144-sup1.cif^{(29.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009075/lh5421Isup2.hkl

e-68-o1144-Isup2.hkl^{(143.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009075/lh5421Isup3.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
N3—H1N3⋯O1ⁱ	0.873 (17)	2.052 (17)	2.9167 (18)	170.8 (16)
C4—H4A⋯O1ⁱ	0.93	2.53	3.251 (2)	135

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Symmetry code: (i) Inline graphic .

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 search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden & Barry, 2000; Hearn et al., 2009; Tripathi et al., 2011). The crystal structures of (E)-N'- (2-Benzyloxybenzylidene)isonicotinohydrazide methanol solvate monohydrate (Naveenkumar et al., 2010), N'-(1-Phenylethylidene)isonicotino hydrazide (Jiang et al., 2009) and N'-(4-Bromophenylsulfonyl) isonicotinohydrazide (Khan et al., 2009) have been reported in the literature. Here, we present the crystal structure of the title compound, (I).

The asymmetric unit of the title compound is shown in Fig. 1. The molecule adopts an E configuration about the central C7═N2 double bond. The 2-methylpent-2-ene group is disordered over two sets of sites, with a refined occupancy ratio of 0.785 (8):0.215 (8). The dihedral angles between the major and minor components of the 2-methylbut-2-ene (C11–C15:C11A–C15A) group is 35.9 (13)°.

In the crystal, Fig. 2, the adjacent molecules are connected via bifurcated N—H···O and C—H···O hydrogen bonds (Table 1), generating R¹₂(7) ring motifs (Bernstein et al., 1995), resulting in supramolecular [001] chains.

Experimental

The title compound was prepared by the reaction of citral, 3,7-dimethylocta- 2,6-dienal (0.15 g, 1 mmol) with isoniazid (0.14 g, 1 mmol) in ETOH/H₂O (3:1, v/v, 10 mL). After stirring for 3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue washed with cold ethyl alcohol and then with ethyl ether to afford the title compound. Colorless blocks of the latter compound suitable for X-ray structure determination were recrystallized from ETOH by the slow evaporation of the solvent at room temperature.