(2E)-1-(2-Methyl-4-phenyl­quinolin-3-yl)-3-(3-methyl­thio­phen-2-yl)prop-2-en-1-one

R Prasath; P Bhavana; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536813004753

. 2013 Feb 23;69(Pt 3):o426–o427. doi: 10.1107/S1600536813004753

(2E)-1-(2-Methyl-4-phenylquinolin-3-yl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one

R Prasath ^a, P Bhavana ^a,^‡, Seik Weng Ng ^b,^c, Edward R T Tiekink ^b,^*

PMCID: PMC3588408 PMID: 23476599

Abstract

In the title compound, C₂₄H₁₉NOS, the quinoline residue (r.m.s. deviation = 0.018 Å) is essentially orthogonal to both the phenyl [dihedral angle = 88.95 (8)°] and 2-thienyl [81.98 (9)°] rings. The carbonyl O atom lies to one side of the quinoline plane, the carbonyl C atom is almost coplanar and the remaining atoms of the chalcone residue lies to the other side, so that overall the molecule has an L-shape. The conformation about the ethylene bond [1.340 (2) Å] is E. In the crystal, a supramolecular chain with the shape of a square rod aligned along the b-axis direction is sustained by C—H⋯π interactions, the π-systems being the heterocyclic rings.

Related literature

For background details and the biological application of quinoline and quinoline chalcones, see: Joshi et al. (2011 ▶); Prasath & Bhavana (2012 ▶); Kalanithi et al. (2012 ▶); Prasath et al. (2013 ▶). For the structure of the dimethyl-substituted quinolinyl compound without a methyl substituent on the 2-thienyl ring, see: Prasath et al. (2011 ▶).

Experimental

Crystal data

C₂₄H₁₉NOS
M _r = 369.46
Triclinic,
a = 10.0815 (7) Å
b = 10.2956 (7) Å
c = 10.5403 (7) Å
α = 71.013 (6)°
β = 78.697 (5)°
γ = 70.412 (6)°
V = 969.99 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.780, T _max = 1.000
8430 measured reflections
4473 independent reflections
3484 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.135
S = 1.03
4473 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(21.2KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004753/hb7043sup1.cif

e-69-0o426-sup1.cif^{(21.2KB, cif)}

Click here for additional data file.^{(219.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004753/hb7043Isup2.hkl

e-69-0o426-Isup2.hkl^{(219.1KB, hkl)}

Click here for additional data file.^{(7.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813004753/hb7043Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the S1,C20–C23 and N1,C1,C6–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1ⁱ	0.93	2.88	3.688 (2)	146
C22—H22⋯Cg2ⁱⁱ	0.93	2.60	3.457 (2)	153

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

Acknowledgments

PB and RP gratefully acknowledge the Council of Scientific and Industrial Research (CSIR), India, for research grant 02 (0076)/12/EMR-II and Senior Research Fellowship (09/919/(0014)/2012 EMR-I), respectively. We 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

In addition to their being valuable intermediates in organic synthesis (Prasath & Bhavana, 2012; Joshi et al., 2011), quinoline and heterocyclic analogues, such as chalcones, exhibit a variety of biological activities, e.g. anti-plasmodial, anti-microbial and anticancer activities (Prasath et al., 2013; Kalanithi et al., 2012). The title quinolinyl/chalcone bearing a thienyl substituent, (I), was investigated in the context of the above.

In (I), Fig. 1, the phenyl ring is perpendicular to the quinolinyl residue (r.m.s. deviation = 0.018 Å), forming a dihedral angle of 88.95 (8)°. The 3-thienyl ring also occupies a position approximately orthogonal to the quinolinyl residue with a dihedral angle of 81.98 (9)°. With respect to the plane through the quinolinyl residue, the carbonyl-O1 atom lies to one side, the carbonyl-C17 atom is almost co-planar and the remaining chalcone residue lies to the other side so that the molecule has an L-shape. The conformation about the ethylene bond [1.340 (2) Å] is E. A similar conformation and displacement of atoms was found in the most closely related structure, namely that of the recently reported (2E)-1-(2,4-dimethylquinolin-3-yl)-3-(thiophen-2-yl)prop-2-en-1-one (Prasath et al., 2011).

The most notable feature of the crystal packing is the formation of supramolecular chains along the b axis and sustained by C—H···π interactions between quinolinyl-C₆—H4 and the 3-thienyl ring, and between 3-thienyl-H22 and the pyridyl ring, Fig. 2 and Table 1. Owing to the L-shape of the molecule, the chain has the shape of a square rod. Chains stack with no specific interactions between them, Fig. 3.

Experimental

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (1.3 g, 0.005 M), 3-methylthiophene-2-carbaldehyde (630 mg, 0.005 M) and KOH (0.5 g) in distilled ethanol (50 ml) was stirred for 12 h at room temperature. The resulting mixture was neutralized with dilute acetic acid. The deposited solid was filtered, dried and purified by column chromatography using a 1:1 mixture of ethyl acetate and hexane. Re-crystallization was by slow evaporation of an acetone solution of (I), which yielded colourless prisms in 76% yield; M.pt: 453–455 K.