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

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

doi:10.1107/S1600536811036154

. 2011 Sep 14;67(Pt 10):o2597. doi: 10.1107/S1600536811036154

4-(4-Chlorophenyl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octahydroquinoline-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: PMC3201290 PMID: 22064694

Abstract

The six-membered N-heterocyclic ring of title compound, C₁₇H₁₇ClN₂O, is fused with a methyl-substituted cyclohexene ring. The nitrogen-bearing ring has an envelope conformation with the benzene ring-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1)° to the latter plane. The cyclohexene ring adopts a half-chair conformation. In the crystal, two molecules are linked about a center of inversion by pairs of N–H⋯O hydrogen bonds, generating dimers. An ethylene portion is disordered over two orientations in a 1:1 ratio. The crystal studied was a non-merohedral twin with a 15.3 (1)% minor component.

Related literature

For a similar compound that has two more H atoms, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₁₇ClN₂O
M _r = 300.78
Monoclinic,
a = 11.0699 (7) Å
b = 7.6018 (3) Å
c = 18.2247 (9) Å
β = 100.505 (6)°
V = 1507.92 (13) Å³
Z = 4
Cu Kα radiation
μ = 2.24 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.554, T _max = 0.896
25955 measured reflections
6143 independent reflections
3143 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.273
S = 1.10
6140 reflections
199 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.46 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/S1600536811036154/xu5321sup1.cif

e-67-o2597-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036154/xu5321Isup2.hkl

e-67-o2597-Isup2.hkl^{(300.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036154/xu5321Isup3.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	0.88	2.07	2.923 (3)	162

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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

The compound (Scheme I) is a side product that was isolated along with 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, the expected product (Asiri et al., 2011); the proportion of the two compounds is unknown. The compound has one set of carbon-carbon double-bonds whereas the expected product has two, i.e., it has two more hydrogen atoms. Futhermore, the double-bond is now located in the methyl-substituted cyclohexene ring. The six-membered ring bearing an N atom that is fused with the cyclohexene ring. The nitrogen-bearing ring has the benzene-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1) °. The cyclohexene ring adopts a half-chair conformation; an ethylene portion is disordered over two positions in a 1:1 ratio (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.

One crystal was characterized as 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, the expected product (Asiri et al., 2011). The second type of crystal is not aromatic and it has two extra hydrogen atoms in the nitrogen-bearing ring (Scheme I).