4-(4-Chloro­phen­yl)-8-methyl-2-oxo-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbonitrile

Abdullah M Asiri; Abdulrahman O Al-Youbi; Hassan M Faidallah; Khadija O Badahdah; Seik Weng Ng

doi:10.1107/S1600536811036142

. 2011 Sep 14;67(Pt 10):o2596. doi: 10.1107/S1600536811036142

4-(4-Chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

Abdullah M Asiri ^a,^b, Abdulrahman O Al-Youbi ^a, Hassan M Faidallah ^a, Khadija O Badahdah ^a, Seik Weng Ng ^c,^a,^*

PMCID: PMC3201532 PMID: 22064998

Abstract

The six-membered N-heterocyclic ring of the title compound, C₁₇H₁₅ClN₂O, is fused with a methyl-substituted cyclohexene ring. The approximately planar nitrogen-bearing ring (r.m.s. deviation 0.019 Å) is aromatic, and the N atom shows a trigonal–planar coordination; its benzene substituent is aligned at 77.1 (1) °. The cyclohexene ring adopts a half-chair conformation. In the crystal, inversion-related molecules are linked by pairs of N—H⋯O hydrogen bonds, generating dimers.

Related literature

For a related compound, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₁₅ClN₂O
M _r = 298.76
Monoclinic,
a = 18.6304 (4) Å
b = 18.7399 (4) Å
c = 8.5209 (2) Å
β = 90.229 (2)°
V = 2974.89 (11) Å³
Z = 8
Cu Kα radiation
μ = 2.27 mm⁻¹
T = 100 K
0.30 × 0.03 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.550, T _max = 0.935
10387 measured reflections
3014 independent reflections
2682 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.187
S = 1.03
3014 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036142/xu5320sup1.cif

e-67-o2596-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036142/xu5320Isup2.hkl

e-67-o2596-Isup2.hkl^{(148KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036142/xu5320Isup3.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
N1—H1⋯O1ⁱ	0.91 (4)	1.84 (4)	2.744 (3)	174 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank King Abdulaziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have reported the synthesis of 2-oxo-4-phenyl-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile by using the reaction of benzaldehyde, 1-tetralone and ethyl cyanoacetate. The last reactant is incorporated into the product to form a part of the six-membered nitrogen-bearing ring, which is now endowed with an exocyclic cyanide group (Asiri et al., 2011). In the present study, the use of 2-methylcyclohexane leads to the formation of the analogous compound with a cyclohexene ring fused with the six-membered nitrogen-bearing ring (Scheme I). The planar nitrogen-bearing ring (r.m.s. deviation 0.019 Å) is aromatic, and the N atom shows trigonal planar coordination; its benzene substituent is aligned at 77.1 (1) °. The cyclohexene ring adopts a half-chair conformation (Fig. 1). Two molecules are linked about a center-of-inversion by an N–H···O hydrogen bond to generate a dimer (Table 1).

Experimental

4-Chlorobenzaldehyde (1.4 g, 10 mmol), 2-methylcyclohexanone (1.2 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) were heated in ethanol (50 ml) for 6 h. The solid product was collected, washed with water and then recrystallized from ethanol.