2-Oxo-4-(thio­phen-2-yl)-1,2,5,6-tetra­hydro­benzo[h]quinoline-3-carbonitrile

Abdullah M Asiri; Hassan M Faidallah; Abdulrahman O Al-Youbi; Khalid A Alamry; Seik Weng Ng

doi:10.1107/S1600536811033915

. 2011 Aug 27;67(Pt 9):o2472. doi: 10.1107/S1600536811033915

2-Oxo-4-(thiophen-2-yl)-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile

Abdullah M Asiri ^a, Hassan M Faidallah ^a, Abdulrahman O Al-Youbi ^a, Khalid A Alamry ^a, Seik Weng Ng ^b,^a,^*

PMCID: PMC3200622 PMID: 22065622

Abstract

In the molecule of the title compound, C₁₈H₁₂N₂OS, the tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH₂CH₂– fragment, the benzene ring and the pyridine ring being twisted by 16.0 (1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 59.5 (2)° (for the major disordered thienyl component) in order to avoid crowding the cyanide substituent. In the crystal, two molecules are linked by a pair of N—H⋯O hydrogen bonds to form a centrosymmetric dimer. The thienyl ring is disordered over two sites in a 72.7 (2):27.3 ratio.

Related literature

For background to the anticancer properties of this class of compounds, see: Rostom et al. (2011 ▶) .

Experimental

Crystal data

C₁₈H₁₂N₂OS
M _r = 304.36
Triclinic,
a = 6.9952 (3) Å
b = 9.1809 (4) Å
c = 11.1837 (5) Å
α = 93.990 (4)°
β = 95.293 (4)°
γ = 100.903 (4)°
V = 699.48 (5) Å³
Z = 2
Cu Kα radiation
μ = 2.07 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.575, T _max = 0.682
5795 measured reflections
2740 independent reflections
2600 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.098
S = 1.07
2740 reflections
216 parameters
19 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.45 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/S1600536811033915/xu5294sup1.cif

e-67-o2472-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033915/xu5294Isup2.hkl

e-67-o2472-Isup2.hkl^{(134.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033915/xu5294Isup3.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	0.89 (1)	1.97 (1)	2.851 (1)	173 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The compound (Scheme I) belongs to a series of cyano-pyridinones that have been evaluated for their anticancer properties (Rostom et al., 2011). The tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH₂CH₂– fragment, the benzene ring and the pyridine ring being twisted by 16.0 (1)°. The 4-subsituted aromatic ring is bent away from the pyridine ring by 59.5 (2) ° in order to avoid crowding the cyanide substituent (Fig. 1). Two molecules are linked by an N—H···O hydrogen bonds to form a centrosymmetric dimer (Table 1).

Experimental

A mixture of thiophene-2-carbaldehyde (1.10 g, 10 mmol), 1-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool, and the yellow precipitate that formed was filtered, washed with water, dried and recrystallized from ethanol; m.p. 622–623 K.