8-Methyl-2-oxo-4-(thio­phen-2-yl)-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbonitrile

Abdullah M Asiri; Hassan M Faidallah; Alaa Anwar Ahmad Saqer; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S160053681202836X

. 2012 Jun 30;68(Pt 7):o2291–o2292. doi: 10.1107/S160053681202836X

8-Methyl-2-oxo-4-(thiophen-2-yl)-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

Abdullah M Asiri ^a,^b,^‡, Hassan M Faidallah ^a, Alaa Anwar Ahmad Saqer ^a,^b, Seik Weng Ng ^c, Edward R T Tiekink ^c,^*

PMCID: PMC3394069 PMID: 22798934

Abstract

In the title compound, C₁₅H₁₄N₂OS, the pyridinone ring in the fused-ring system is nearly planar (r.m.s. deviation = 0.011 Å) and the cyclohexene ring has a twisted half-boat conformation with the methylene C atom adjacent to the methine C atom deviating by 0.592 (7) Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.108 Å). The thienyl ring is disordered over two almost coplanar positions of opposite orientation in a 0.649 (4):0.351 (4) ratio, and forms dihedral angles of 51.4 (3) (major component) and 54.2 (3)°, respectively, with the pyridinone ring. In the crystal, inversion-related molecules associate via an eight-membered {⋯HNCO}₂ synthon and these are linked into a linear supramolecular chain along the a axis by weak π–π interactions that occur between centrosymmetrically related pyridinone rings [centroid–centroid distance = 3.889 (2) Å].

Related literature

For background to the cardiotonic and anti-inflammatory properties of this class of compounds, see: Behit & Baraka (2005 ▶); Girgis et al. (2007 ▶). For a related structure, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂OS
M _r = 270.34
Triclinic,
a = 7.6443 (3) Å
b = 9.6909 (5) Å
c = 9.9852 (5) Å
α = 67.003 (5)°
β = 80.869 (4)°
γ = 76.108 (4)°
V = 659.26 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.798, T _max = 1.000
9707 measured reflections
3041 independent reflections
2356 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.088
wR(F ²) = 0.230
S = 1.07
3041 reflections
185 parameters
33 restraints
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202836X/xu5572sup1.cif

e-68-o2291-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202836X/xu5572Isup2.hkl

e-68-o2291-Isup2.hkl^{(149.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681202836X/xu5572Isup3.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—H1n⋯O1ⁱ	0.88	1.94	2.801 (4)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to King Abdulaziz University for providing the research facilities. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound (I) is a member of a series of cyano-pyridinones that have been evaluated for their cardiotonic (Behit & Baraka, 2005) and anti-inflammatory (Girgis et al., (2007) properties. Herein, the crystal and molecular structures of (I) are described.

In (I), Fig. 1, the pyridyl ring in the fused ring system is planar [r.m.s. deviation = 0.011 Å] and the cyclohexene ring has a twisted half-boat conformation with the methylene-C3 atom lying -0.592 (7) Å above the plane defined by the remaining five atoms [r.m.s. deviation = 0.108 Å]. There are two orientations of the thienyl ring [co-planar, with a dihedral angle of 4.4 (4)°, and of opposite orientations] both of which are inclined with respect to the pyridyl ring, forming dihedral angles of 51.4 (3)° [major component] and 54.2 (3)°, respectively. The molecular structure of (I) resembles that found in a literature structure with the exception of the C2—C3 conformation which is fused to a benzene ring (Asiri et al., 2011).

The familiar eight-membered centrosymmetric amide {···HNCO}₂ synthon is observed in the crystal packing, Table 1. These are connected into a linear supramolecular chain along the a axis by π—π interactions that occur between centrosymmetrically related pyridyl rings [inter-centroid distance = 3.889 (2) Å for symmetry operation 1 - x, 1 - y, 1 - z], Fig. 2. Chains assemble into layers in the ab plane and stack along the c axis being separated by hydrophobic interactions, Fig. 3.

Experimental

A mixture of the thiophene-2-carboxaldehyde (1.1 g, 0.01 M), 2-methylcyclohexanone (1.12 g, 0.01 M), ethyl cyanoacetate (1.1 g, 0.01 M) and ammonium acetate (6.2 g, 0.08 M) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool. The formed precipitate was filtered, washed with water, dried and recrystallized from ethanol as yellow crystals, M. pt: 525–527 K. Yield: 72%.