(2E)-3-(2-Chloro-8-methyl­quinolin-3-yl)-1-(2,4-di­methyl­quinolin-3-yl)prop-2-en-1-one

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

doi:10.1107/S1600536813019405

. 2013 Jul 20;69(Pt 8):o1275. doi: 10.1107/S1600536813019405

(2E)-3-(2-Chloro-8-methylquinolin-3-yl)-1-(2,4-dimethylquinolin-3-yl)prop-2-en-1-one

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

PMCID: PMC3793770 PMID: 24109357

Abstract

In the molecule of the title compound, C₂₄H₁₉ClN₂O, the terminal quinolinyl residues are close to perpendicular to each other [dihedral angle 83.72 (4)°]. The quinolinyl residues are connected by and inclined to the prop-2-en-1-one bridge, with the C_ar—C_ar—C—C (ar = aromatic) torsion angles being 71.01 (17) and 20.6 (2)°. The crystal structure features phenyl–carbonyl C—H⋯O interactions and π–π interactions between centrosymmetrically related quinolinyl residues [3.5341 (10) and 3.8719 (9) Å], which together lead to a three-dimensional architecture.

Related literature

For background to quinoline chalcones and for a related structure, see: Prasath et al. (2013 ▶). graphic file with name e-69-o1275-scheme1.jpg

Experimental

Crystal data

C₂₄H₁₉ClN₂O
M _r = 386.86
Triclinic,
a = 7.4150 (5) Å
b = 9.9045 (6) Å
c = 14.0696 (9) Å
α = 71.072 (5)°
β = 88.427 (5)°
γ = 72.552 (5)°
V = 929.66 (10) Å³
Z = 2
Cu Kα radiation
μ = 1.95 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T _min = 0.853, T _max = 1.000
6846 measured reflections
3811 independent reflections
3587 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.095
S = 1.04
3811 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 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) global, I. DOI: 10.1107/S1600536813019405/hb7108sup1.cif

e-69-o1275-sup1.cif^{(28.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019405/hb7108Isup2.hkl

e-69-o1275-Isup2.hkl^{(183KB, hkl)}

Click here for additional data file.^{(7.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813019405/hb7108Isup3.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
C20—H20⋯O1ⁱ	0.95	2.58	3.364 (2)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

RP gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship [grant No. 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 (grant No. UM·C/HIR-MOHE/SC/03).

supplementary crystallographic information

Comment

For the background to biological activities, utility as intermediates in organic synthesis and photophysical properties of quinolines, as well as the bio-activities of quinolinyl chalcones and a related structure, see the Introduction to Prasath et al. (2013).

In (I), Fig. 1, the dihedral angle between the quinolinyl rings is 83.72 (4)°. The conformation about the ethylene bond [C13═C14 = 1.3333 (19) Å] is E. The central prop-2-en-1-one residue, comprising the O1 and C12–C15 atoms, is twisted, as manifested in the O1—C12—C13—C14 torsion angle of 16.4 (2)°. The N1- and N2-containing quinolinyl rings are also twisted with respect to the central bridge, as seen in the C7—C8—C12—C13 and C13—C14—C15—C23 torsion angles of 71.01 (17) and 20.6 (2)°, respectively.

In the most closely related structure available for comparison, (II), namely (2E)-3-(6-chloro-2-methoxyquinolin-3-yl)-1-(5,7-dimethylquinolin-6-yl)prop-2-en-1-one (Prasath et al., 2013), the dihedral angle between the quinolinyl residues is 63.30 (5)°, indicating a more compact configuration than that in (I); the central residue in (II) is planar. Finally, when the structures are viewed normal to the ethylene bond, the pyridyl-N atoms in (I) can be described as anti, whereas they are closer to syn in (II).

In the crystal, linear supramolecular chains are formed by phenyl-C—H···O(carbonyl) interactions, Table 1. These, along with π–π interactions between the rings of centrosymmetrically related N1-quinolinyl residues [3.7578 (9) Å; angle of inclination = 1.91 (7)° for symmetry operation 1 - x, -y, 1 - z] and between the rings of centrosymmetrically related N2-quinolinyl residues [3.5767 (9) Å; angle of inclination = 0.99 (7)° for symmetry operation -x, 2 - y, -z], connect the molecules into a three-dimensional architecture, Fig. 2.

Experimental

A mixture of 2,4-dimethyl-3-acetylquinoline (200 mg, 0.001 M) and 2-chloro-8-methylquinoline-3-carbaldehyde (200 mg, 0.001 M) in methanol (20 ml) containing 0.2 g of potassium hydroxide was stirred at room temperature for 12 h. Then the reaction mixture was neutralized with dilute acetic acid and the resultant solid was filtered, dried and purified by column chromatography using ethyl acetate–hexane (1:1) mixture to afford (I). Re-crystallization was by slow evaporation of an acetone solution of (I), which yielded pale-yellow blocks in 78% yield; m.p. 458–460 K.