(2E,4E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinol­yl)-5-phenyl­penta-2,4-dien-1-one

Wan-Sin Loh; Hoong-Kun Fun; A J Viji; S Sarveswari; V Vijayakumar

doi:10.1107/S1600536810016429

. 2010 May 12;66(Pt 6):o1321. doi: 10.1107/S1600536810016429

(2E,4E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinolyl)-5-phenylpenta-2,4-dien-1-one

Wan-Sin Loh ^a,^‡, Hoong-Kun Fun ^a,^*,^§, A J Viji ^b, S Sarveswari ^b, V Vijayakumar ^b

PMCID: PMC2979425 PMID: 21579414

Abstract

In the title compound, C₂₇H₂₀ClNO, the quinoline ring forms a dihedral angle of 62.53 (5)° with the substituent benzene ring. In the crystal, intermolecular C—H⋯Cl interactions link the molecules into chains along the b axis. Intermolecular C—H⋯N and C—H⋯O hydrogen bonds further consolidate the structure into a three-dimensional network. The unit cell contains four solvent-accessible voids, each with a volume of 35 Å³, but no significant electron density was found in them.

Related literature

For the background to and the biological activity of quinolines, see: Bhat et al. (2005 ▶); Markees et al. (1970 ▶); Campbell et al. (1998 ▶). For related structures, see: Loh et al. (2010a ▶,b ▶); Shahani et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₇H₂₀ClNO
M _r = 409.89
Monoclinic,
a = 6.2464 (3) Å
b = 22.5672 (11) Å
c = 15.2748 (7) Å
β = 94.620 (1)°
V = 2146.20 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.35 × 0.26 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.935, T _max = 0.975
22989 measured reflections
6191 independent reflections
4889 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.116
S = 1.03
6191 reflections
351 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016429/fj2295sup1.cif

e-66-o1321-sup1.cif^{(23.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016429/fj2295Isup2.hkl

e-66-o1321-Isup2.hkl^{(303.1KB, 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
C3—H3A⋯N1ⁱ	0.966 (17)	2.484 (19)	3.3681 (16)	152.1 (14)
C11—H11A⋯Cl1ⁱⁱ	0.994 (17)	2.772 (16)	3.6491 (12)	147.4 (14)
C17—H17A⋯O1ⁱⁱⁱ	1.000 (19)	2.596 (19)	3.4398 (17)	142.1 (14)
C27—H27C⋯O1^iv	0.984 (18)	2.517 (19)	3.3892 (16)	147.6 (14)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

The quinoline derivatives are very important compounds because of their wide occurrence in natural products and biologically active compounds (Markees et al., 1970; Campbell et al., 1998). A variety of natural compounds such as vinblastin, combretastatin A-4 and colchicine attack microtubules by interfering with the dynamics of tubulin polymerization and depolymerization, resulting in mitotic arrest. For a structurally simple group of compounds, chalcones have displayed an impressive array of biological activities, among which anti-malarial, anti-protozoal, anti-inflammatory, immunomodulatory, nitric oxide inhibition, tyronase inhibition, cytotoxic and anticancer activities have been cited in the literature (Bhat et al., 2005). In continuation our interest in synthesis of chalcones herein we report a new chalcone (Loh et al., 2010a,b; Shahani et al., 2010).

In the title compound (Fig. 1), the quinoline ring system (C1/N1/C2–C9) is approximately planar with a maximum deviation of 0.009 (1) Å at atom C1. This mean plane of quinoline ring system forms a dihedral angle of 62.53 (5)° with the benzene ring (C21–C26) attached to it. Another benzene ring (C15–C20) is linked with the quinoline ring system by a linkage of pentadione (C10–C14/O1) with a dihedral angle of 80.31 (5)° and the torsion angle between the linkage and the quinoline ring system, C8–C9–C10–C11 is 111.08 (13)°. Bond lengths and angles are comparable to closely related structures (Loh et al., 2010a,b; Shahani et al., 2010).

In the crystal packing (Fig. 2), intermolecular C11—H11A···Cl1 interactions (Table 1) link the molecules into chains down the b axis. Intermolecular C3—H3A···N1, C17—H17A···O1 and C27—H27C···O1 hydrogen bonds (Table 1) further consolidate the structure into a three-dimensional network. The unit cell contains four solvent-accessible voids each with a volume of 35 Å³. Application of the PLATON SQUEEZE procedure (Spek, 2009) showed no electron count in the void.

Experimental

A mixture of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline (0.01 M) and cinnamaldehyde (0.01 M) and a catalytic amount of KOH in distilled ethanol was stirred for about 12 h, the resulting mixture was concentrated to remove ethanol then poured on to ice and neutralized with dilluted acetic acid. The resultant solid was filtered, dried and purified by column chromatography using 1:1 mixture of ethyl acetate and petroleum ether. M.P.: 416–417 K. Yield: 62 %. The solvent used for the crystallisation was a 1:1 mixture of ethyl acetate and petroleum ether.