(2E)-3-(6-Chloro-2-meth­oxy­quinolin-3-yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one acetone monosolvate

R Prasath; S Sarveswari; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536813020217

. 2013 Jul 27;69(Pt 8):o1319. doi: 10.1107/S1600536813020217

(2E)-3-(6-Chloro-2-methoxyquinolin-3-yl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one acetone monosolvate

R Prasath ^a,^‡, S Sarveswari ^b, Seik Weng Ng ^c,^d, Edward R T Tiekink ^c,^*

PMCID: PMC3793806 PMID: 24109393

Abstract

In the title solvate, C₂₉H₂₁ClN₂O₂·C₃H₆O, a prop-2-en-1-one bridge links two quinolinyl residues; the latter are almost perpendicular [dihedral angle = 78.27 (6)°]. The dihedral angle between the quinonyl ring system and its pendant phenyl group is 59.78 (8)°. A small twist in the bridging prop-2-en-1-one group is noted [O=C—C=C torsion angle = −10.6 (3)°]. In the crystal, a three-dimensional architecture arises as a result of C—H⋯O and π–π stacking [centroid–centroid distances = 3.5504 (12)–3.6623 (12) Å].

Related literature

For background details and the biological applications of quinolinyl derivatives, see: Joshi et al. (2011 ▶); Prasath et al. (2013a ▶). For a related structure, see: Prasath et al. (2013b ▶). graphic file with name e-69-o1319-scheme1.jpg

Experimental

Crystal data

C₂₉H₂₁ClN₂O₂·C₃H₆O
M _r = 523.01
Monoclinic,
a = 17.1714 (3) Å
b = 10.7099 (2) Å
c = 14.5248 (2) Å
β = 100.021 (2)°
V = 2630.42 (8) Å³
Z = 4
Cu Kα radiation
μ = 1.58 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T _min = 0.665, T _max = 1.000
11367 measured reflections
5408 independent reflections
4574 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.167
S = 1.03
5408 reflections
346 parameters
H-atom parameters constrained
Δρ_max = 1.47 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2013 ▶); 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

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536813020217/hg5334sup1.cif

e-69-o1319-sup1.cif^{(25.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020217/hg5334Isup2.hkl

e-69-o1319-Isup2.hkl^{(259.5KB, hkl)}

Click here for additional data file.^{(9.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813020217/hg5334Isup3.cml

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
C26—H26⋯O2ⁱ	0.95	2.47	3.319 (3)	149
C30—H30A⋯O1ⁱ	0.98	2.52	3.373 (4)	146
C28—H28⋯O3	0.95	2.57	3.467 (3)	158

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

RP gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship (09/919/(0014)/2012 EMR-I). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

supplementary crystallographic information

Comment

The the title compound, (I), was investigated in connection with on-going studies of quinolinyl chalcones (Prasath et al., 2013a), motivated by their potential anti-bacterial, anti-fungal, anti-malarial and anti-cancer activity (Joshi et al., 2011).

The molecular structure of the quinolinyl derivative, (I), Fig. 1, comprises two quinolinyl residues connected by the ends of a prop-2-en-1-one bridge, in an almost perpendicular relationship; the dihedral angle between the quinolinyl residues is 78.27 (6)°. The phenyl ring is inclined with respect to the quinolinyl residue to which it is attached, forming a dihedral angle of 59.78 (8)°. The conformation about the ethylene bond [C18═C19 = 1.336 (3) Å] is E. A small twist in the bridging prop-2-en-1-one group is manifested in the O1—C17—C18—C19 torsion angle of -10.6 (3)°. An distinct conformation was reported recently for a related structure, namely (2E)-3-(6-chloro-2-methoxyquinolin-3-yl)-1-(2,4-dimethylquinolin-3 - y)prop-2-en-1-one (Prasath et al., 2013b) where the nitrogen atoms are approximately syn as opposed to approximately anti in (I).

In the crystal packing, the quinolinyl and acetone molecules are connected by C—H···O interactions, Table 1. Additional C—H···O contacts and a number of π—π interactions, involving pyridyl, a quinolinyl-C₆ ring and the phenyl group, connect molecules into a three-dimensional architecture [centroid···centroid distances = 3.5504 (12), 3.5747 (12) and 3.6623 (12) Å], Fig. 2.

Experimental

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (260 mg, 0.001 M) and 2,6-dichloroquinoline-3-carbaldehyde (230 mg, 0.001 M) in methanol (20 ml) containing potassium hydroxide (0.2 g) was stirred at room temperature for 12 h. The reaction mixture was then neutralized with dilute acetic acid and the resultant solid was filtered, dried and purified by column chromatography using ethyl acetate - hexane (3:1) mixture to afford compound. Re-crystallization was by slow evaporation of an acetone solution of (I), which yielded blocks in 62% yield; M.pt: 366–368 K.