2-(2,4-Dichloro­phen­yl)-9-phenyl-2,3-di­hydro­thieno[3,2-b]quinoline

K Balamurugan; D Narmadha; J Suresh; S Perumal; P L Nilantha Lakshman

doi:10.1107/S1600536809025380

. 2009 Jul 4;65(Pt 8):o1783. doi: 10.1107/S1600536809025380

2-(2,4-Dichlorophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline

K Balamurugan ^a, D Narmadha ^b, J Suresh ^b, S Perumal ^a, P L Nilantha Lakshman ^c,^*

PMCID: PMC2977236 PMID: 21583489

Abstract

In the title compound, C₂₃H₁₅Cl₂NS, the quinoline system is almost planar [r.m.s. deviation = 0.013 (2) Å]. The phenyl group is disordered over two positions with site occupancies of 0.55 and 0.45, and is oriented in a nearly perpendicular configuration to the quinoline ring [the dihedral angles between the quinoline ring and the major and minor disordered components of the phenyl ring are 81.8 (2) and 71.6 (2)°, respectively]. The dihydrothiene ring adopts an envelope conformation. The dihedral angle between the chlorophenyl ring and the quinoline system is 79.32 (1)°. In the crystal weak C—H⋯π interactions occur.

Related literature

For the biological activity of quinoline derivatives, see: Kalluraya & Sreenivasa (1998 ▶); Maguire et al. (1994 ▶); Doube et al. (1998 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₃H₁₅Cl₂NS
M _r = 408.32
Monoclinic,
a = 11.8860 (5) Å
b = 11.5040 (5) Å
c = 14.0270 (6) Å
β = 94.297 (9)°
V = 1912.61 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 K
0.19 × 0.16 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.917, T _max = 0.951
3917 measured reflections
3363 independent reflections
2577 reflections with I > 2σ(I)
R _int = 0.014
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.091
S = 1.02
3363 reflections
284 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025380/at2782sup1.cif

e-65-o1783-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025380/at2782Isup2.hkl

e-65-o1783-Isup2.hkl^{(161.6KB, hkl)}

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
C8—H8⋯Cg2ⁱ	0.93	2.92	3.818 (2)	162
C21—H21⋯Cg3ⁱⁱ	0.93	2.71	3.636 (2)	172

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Symmetry codes: (i) Inline graphic ; (ii) . Cg2 and Cg3 are the centroids of the N1/C2–C6 and C2/C3/C7–C10 rings, respectively.

Acknowledgments

JS and DN thank the Management of The Madura College, Madurai, for their constant support.

supplementary crystallographic information

Comment

Quinoline exists as backbone in many natural products and pharmacologically important compounds. Their widerange of biological activities include 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 (I), (Fig. 1), the quinoline ring is planar and is oriented to the disordered phenyl ring in nearly perpendicular configuration. The dihendral angle between the major and minor components of the disordered phenyl rings is 26.6 (4)°. The dihydrothieno ring adopts envelope conformation with C18 being the flap atom. The puckering parameters are q₂ = 0.333 (2) Å and φ₂ = 319.7 (3)° (Cremer & Pople, 1975). The dihedral angle between the chlorophenyl ring and the quinoline ring is 79.32 (1)°.

In the crystal structure, there is no classical hydrogen bonds. The crystal packing is stabilized by two weak C—H···π interactions (Table 1; Cg2 and Cg3 refer to ring centroids of N1/C2–C6 and C2/C3/C7–C10, respectively).

Experimental

A mixture of 5-(2,4-dichlorophenyl)dihydrothiophen-3(2H)-one, (1 mmol), 2-aminobenzophenone (1 mmol) and trifluroaceticacid (1.5 mmol) was taken in a 10 ml quartz vial and placed in the Biotage microwave oven. The vial was sealed and subjected to microwave irradiation. The irradiation was programmed at (273 K, 25 W, 0 bar, Absorption level: very high) for 30 min. (After a period of 1–2 min, the temperature reached a plateau, 273 K, and remained constant). After N₂ gas jet cooling to room temperature (3 min), the reaction mixture was neutralized with NaHCO₃ and extracted in CH₂Cl₂ (2 X 5 ml), dried over MgSO₄ and concentrated in vacuo to give the crude product which was further purified either by a short column chromatography (silica gel, EtOAc-petroleumether, 2:8) to afford the corresponding pure quinoline derivative [melting point: 437–438 K, yield: 75%].