N′-(Cyclo­hexyl­carbon­yl)isonicotino­hydrazide

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

doi:10.1107/S1600536809027469

. 2009 Jul 18;65(Pt 8):o1912. doi: 10.1107/S1600536809027469

N′-(Cyclohexylcarbonyl)isonicotinohydrazide

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

PMCID: PMC2977321 PMID: 21583599

Abstract

In the title compound, C₁₃H₁₇N₃O₂, the mean plane of the cyclohexane ring forms a dihedral angle of 33.12 (5)° with the pyridine ring. The two O atoms are twisted away from each other, as indicated by the C—N—N—C torsion angle of −74.97 (9)°. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds. The structure is also stabilized by C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For applications of isoniazid derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶). For the preparation, see: Besra et al. (1993 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₃H₁₇N₃O₂
M _r = 247.30
Orthorhombic,
a = 9.1184 (2) Å
b = 11.5989 (2) Å
c = 12.1684 (2) Å
V = 1286.97 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.60 × 0.40 × 0.33 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.941, T _max = 0.971
27969 measured reflections
3210 independent reflections
3124 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.084
S = 1.11
3210 reflections
231 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809027469/kj2133sup1.cif

e-65-o1912-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027469/kj2133Isup2.hkl

e-65-o1912-Isup2.hkl^{(157.5KB, 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⋯N1ⁱ	0.911 (18)	2.095 (18)	2.9456 (10)	155.0 (16)
N3—H1N3⋯O2ⁱⁱ	0.900 (16)	1.854 (16)	2.7486 (9)	172.4 (14)
C2—H2⋯O1ⁱⁱⁱ	1.017 (18)	2.527 (18)	3.4971 (11)	159.4 (14)
C4—H4⋯O1^iv	0.948 (15)	2.502 (15)	3.3062 (10)	142.6 (12)
C10—H10B⋯Cg1^v	1.01 (2)	2.78 (3)	3.7299 (14)	157.1 (16)
C13—H13A⋯Cg1^vi	0.993 (15)	2.958 (16)	3.7039 (10)	132.7 (12)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the C1/C2/N1/C3–C5 ring.

Acknowledgments

This research is supported by Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815005). HKF and CSY thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY thanks the Malaysian Government and USM for the award of the post of Research Officer under the Science Fund Grant (No. 305/PFIZIK/613312). HSNK is grateful for a USM fellowship for financial assistance.

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.

Bond lengths and angles of the title compound (I), (Fig. 1) are within the normal range (Allen et al., 1987). The mean plane of cyclohexane ring forms dihedral angle of 33.12 (5)° with the pyridine ring. The O1 and O2 atoms are twisted away from each other as is indicated by torsion angle C6–N2–N3–C7 [-74.97 (9)°]. In the crystal structure, the molecules are linked into three-dimensional network by the intermolecular N2—H1N2···N1, N3—H1N3···O2, C2—H2···O1 and C4—H4···O1 hydrogen bonds. The structure is also stabilized by C—H···π interactions (Table 1).

Experimental

The isoniazid (INH) derivative was prepared following the procedure by literature (Besra et al., 1993). Dry dichloromethane (30 ml) and 4-dimethylaminopyridine (4-DMAP) (1.2 eq) was added to cyclohexane carbonyl chloride followed by INH (1.1 eq). The reaction mixture was kept in an ice bath for 1 h and then left stirring under nitrogen overnight at room temperature. Dichloromethane (20 ml) was added to the reaction mixture, which was then washed with water, and the organic layer dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure to afford the crude product which was purified by column chromatography and recrystallized from methanol to afford colorless crystals.