1-(6-Chloro-2-methyl-4-phenyl-3-quinol­yl)ethanone

Hoong-Kun Fun; Wan-Sin Loh; S Sarveswari; V Vijayakumar; B Palakshi Reddy

doi:10.1107/S1600536809040306

. 2009 Oct 10;65(Pt 11):o2688–o2689. doi: 10.1107/S1600536809040306

1-(6-Chloro-2-methyl-4-phenyl-3-quinolyl)ethanone

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a, S Sarveswari ^b, V Vijayakumar ^b, B Palakshi Reddy ^b

PMCID: PMC2971397 PMID: 21578294

Abstract

In the title compound, C₁₈H₁₄ClNO, the quinoline ring system is approximately planar with a maximum devation of 0.022 (1) Å and forms a dihedral angle of 62.70 (3)° with the phenyl ring. In the crystal, pairs of C—H⋯O intermolecular hydrogen bonds link neighbouring molecules into inversion dimers, forming R ₂ ²(14) ring motifs. These inversion dimers are stacked along the b axis. The structure is further stabilized by C—H⋯π interactions.

Related literature

For reference bond-length data, see: Allen et al. (1987 ▶). For background to quinolines, see: Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1988 ▶); Maguire et al. (1994 ▶); Kalluraya & Sreenivasa (1998 ▶); Roma et al. (2000 ▶); Chen et al. (2001 ▶); Skraup (1880 ▶); Katritzky & Arend (1998 ▶); Jiang & Si (2002 ▶). For the biological activity of chalcones, see: Dimmock et al. (1999 ▶); Yamazaki et al. (2002 ▶). For a related structure, see: Fun et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₈H₁₄ClNO
M _r = 295.75
Monoclinic,
a = 10.4633 (2) Å
b = 7.7959 (1) Å
c = 17.5925 (3) Å
β = 90.887 (1)°
V = 1434.86 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.57 × 0.34 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.865, T _max = 0.932
32340 measured reflections
7613 independent reflections
6588 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.107
S = 1.07
7613 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809040306/wn2352sup1.cif

e-65-o2688-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040306/wn2352Isup2.hkl

e-65-o2688-Isup2.hkl^{(372.5KB, 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
C15—H15A⋯O1ⁱ	0.93	2.55	3.2047 (10)	128
C11—H11A⋯Cg1ⁱⁱ	0.93	2.78	3.6416 (7)	155
C13—H13A⋯Cg2ⁱⁱⁱ	0.93	2.92	3.6255 (8)	133

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C9/N1 and C10–C15 ring systems, respectively.

Acknowledgments

HKF and WSL thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of the post of Assistant Research Officer under the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991; Michael, 1997) and biologically active compounds (Markees et al., 1970; Campbell et al., 1988). A large variety of quinolines have interesting physiological activities and have found attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks (Maguire et al., 1994; Kalluraya & Sreenivasa, 1998; Roma et al., 2000; Chen et al., 2001; Skraup, 1880). Many synthetic methods such as the Skraup, Doebner-Von Miller, Friedländer and Combes reactions have been developed for the preparation of quinolines, but due to their great importance, the synthesis of new derivatives of quinoline remains an active research area (Katritzky & Arend, 1998; Jiang & Si, 2002). Chalcones are open-chain flavonoids, possessing a variety of biological activities, including antioxidant, anti-inflammatory, antimicrobial, antiprotozoal, antiulcer, as well as other activities (Dimmock et al., 1999). More importantly, chalcones have shown several anticancer activities, such as inhibitors of cancer cell proliferation, carcinogenesis, and metastasis (Yamazaki et al., 2002).

In the crystal structure (Fig. 1), bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to those in a closely related structure (Fun et al., 2009). The quinoline ring system (C1–C9/N1) is approximately planar, with a maximum devation of 0.022 (1) Å at atom C1. The phenyl ring (C10–C15) forms a dihedral angle of 62.70 (3)° with the mean plane of the quinoline ring system. In the crystal packing (Fig. 2), pairs of C15—H15A···O1 hydrogen bonds link neighbouring molecules into dimers, forming R₂²(14) ring motifs (Bernstein et al., 1995). These inversion dimers are stacked along the b axis. The crystal structure is further stabilized by C—H···π interactions (Table 1), involving the C1–C9/N1 (centroid Cg1) and C10–C15 (centroid Cg2) ring systems.

Experimental

A mixture of 2-amino-5-chlorobenzophenone (2.3 g, 0.01 mol) and acetylacetone (1.0 g, 0.01 mol) with 0.15 ml concentrated HCl in a beaker was subjected to microwave irradiation for about 6 min. After completion of the reaction (monitored by TLC), the reaction mixture was washed with saturated solvent NaHCO₃ (10 ml) and then it was dried. After that it was washed with petroleum ether and recrystallized with chloroform (M. p. 224–226°C). IR (cm^-1): 1704, 1480, 1385, 840, 711.