2-Chloro-12-phenyl-6,7,8,9,10,11-hexa­hydro­cyclo­octa­[b]quinoline

Ayoob Bazgir; Ali Mohammad Astaraki

doi:10.1107/S1600536808009239

. 2008 Apr 10;64(Pt 5):o831. doi: 10.1107/S1600536808009239

2-Chloro-12-phenyl-6,7,8,9,10,11-hexahydrocycloocta[b]quinoline

Ayoob Bazgir ^a,^*, Ali Mohammad Astaraki ^a

PMCID: PMC2961081 PMID: 21202320

Abstract

In the molecule of the title compound, C₂₁H₂₀ClN, the quinoline group is nearly planar and is oriented at a dihedral angle of 77.21 (3)° with respect to the phenyl ring. The conformation of the cyclooctane ring is twist-boat. In the crystal structure, there are some weak π–π interactions [centroid-to-centroid distances of 3.7414 (11) and 3.8633 (12) Å] between the rings of the quinoline groups.

Related literature

For general background, see: Kalluraya & Sreenivasa (1998 ▶); Doube et al. (1998 ▶); Maguire et al. (1994 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₁H₂₀ClN
M _r = 321.83
Triclinic,
a = 9.837 (2) Å
b = 9.980 (2) Å
c = 10.175 (2) Å
α = 74.600 (17)°
β = 70.575 (16)°
γ = 61.829 (15)°
V = 823.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 (2) K
0.5 × 0.5 × 0.25 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical; shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2002 ▶) T _min = 0.889, T _max = 0.949
8123 measured reflections
3801 independent reflections
3493 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.126
S = 1.03
3801 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009239/hk2449sup1.cif

e-64-0o831-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009239/hk2449Isup2.hkl

e-64-0o831-Isup2.hkl^{(182.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author is grateful to the Islamic Azad University, Dorood Branch, for financial support.

supplementary crystallographic information

Comment

Quinoline nucleus is a backbone of many natural products and pharmacologicallly significant compounds displaying a broad range of biological activities and many functionalized quinolines are widely used as antimalarial, antiasthmatic, antiinflamatory, antibacterial, antihypertensive and tyrosine kinase PDGF-RTK inhibiting agents (Kalluraya & Sreenivasa, 1998; Doube et al., 1998; Maguire et al., 1994). We report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (N1/C1/C6-C8/C15) and C (C16-C21) are, of course, planar, and they are oriented at dihedral angles of A/B = 0.88 (3)°, A/C = 76.76 (4)° and B/C = 77.64 (3)°. So, rings A and B are also nearly coplanar. The dihedral angle between the coplanar ring system and ring C is 77.21 (3)°.

In the crystal structure, the weak π–π interactions between the two adjacent A rings and A and B rings, with centroid-centroid distances of 3.7414 (11) Å and 3.8633 (12) Å, may be effective in the stabilization of the structure (Fig. 2).

Experimental

A mixture of 2-amino-5-chlorophenyl(phenyl)methanone (0.23 g, 1 mmol), cyclooctanone (1.26 g, 1 mmol) and Dewax-50 W ion exchange resin (0.3 g) was heated at 353 K. After 2 h the reaction mixture was washed with ethyl acetate (10 ml). Evaporation of the solvent followed by recrystallization from ethanol to afford the pure product (yield; 0.278 g, 75%).