(E)-3-[4-(Dimethyl­amino)­phen­yl]-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one 0.7-hydrate

Wan-Sin Loh; Hoong-Kun Fun; S Sarveswari; V Vijayakumar; R Prasath

doi:10.1107/S1600536811019088

. 2011 May 25;67(Pt 6):o1521–o1522. doi: 10.1107/S1600536811019088

(E)-3-[4-(Dimethylamino)phenyl]-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one 0.7-hydrate

Wan-Sin Loh ^a,^‡, Hoong-Kun Fun ^a,^*,^§, S Sarveswari ^b, V Vijayakumar ^b, R Prasath ^b

PMCID: PMC3120557 PMID: 21754884

Abstract

In the title compound, C₂₇H₂₄N₂O·0.7H₂O, the quinoline ring system is approximately planar, with a maximum deviation of 0.011 (1) Å, and forms dihedral angles of 74.70 (4) and 80.14 (4)° with the phenyl and benzene rings, respectively. In the crystal, the molecules are linked to the water molecules via intermolecular O—H⋯N hydrogen bonds and further stabilized by C—H⋯π interactions involving the centroid of the benzene ring of the quinoline group. This benzene ring is observed to form a π–π interaction with an adjacent pyridine ring [centroid–centroid distance = 3.7120 (6) Å].

Related literature

For background to chalcone derivatives, see: Sarveswari & Vijayakumar (2011 ▶); Sarveswari et al. (2010 ▶); Loh et al. (2010b ▶); Shahani et al. (2010 ▶). For related structures, see: Fun et al. (2009 ▶); Loh et al. (2010a ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₇H₂₄N₂O·0.7H₂O
M _r = 405.09
Triclinic,
a = 9.2653 (2) Å
b = 10.6076 (2) Å
c = 12.2347 (2) Å
α = 66.409 (1)°
β = 87.758 (1)°
γ = 80.308 (1)°
V = 1085.70 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.47 × 0.31 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.964, T _max = 0.983
28425 measured reflections
8843 independent reflections
6883 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.158
S = 1.05
8843 reflections
289 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.25 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/S1600536811019088/rz2594sup1.cif

e-67-o1521-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019088/rz2594Isup2.hkl

e-67-o1521-Isup2.hkl^{(432.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811019088/rz2594Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N1ⁱ	0.85 (2)	2.01 (2)	2.8650 (17)	176 (2)
C14—H14A⋯Cg1ⁱⁱ	0.95	2.81	3.6395 (14)	147

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

As part of our ongoing research on chalcones (Sarveswari & Vijayakumar, 2011; Sarveswari et al., 2010; Loh et al., 2010b; Shahani et al., 2010), herein we report the synthesis of new chalcone derivative.

The asymmetric unit of title compound, (Fig. 1), consists of one (E)-3-(4-(dimethylamino)phenyl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one molecule and one water molecule with the occupancy of 0.7. The quinoline ring system (C1–C9/N1) is approximately planar with a maximum deviation of 0.011 (1) Å at atom C9 and forms dihedral angles of 74.70 (4) and 80.14 (4)° with the benzene and phenyl rings (C10–C15 & C19–C24), respectively. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Fun et al., 2009; Loh et al., 2010a).

In the crystal packing (Fig. 2), the molecules are linked to the water molecules via intermolecular O1W—H1W1···N1 hydrogen bonds (Table 1) and further stabilized by C—H···π interactions (Table 1), involving the centroids of the benzene ring (C1–C6; Cg1) of the quinoline unit. This benzene ring is observed to form a π–π interactions with an adjacent pyridine ring (N1/C1/C6–C9; Cg2) in the stabilization of the crystal structure, with the separation Cg1···Cg2ⁱⁱⁱ = 3.7120 (6) Å [symmetry code: (iii) 1 - x, -y, -z].

Experimental

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (2.6 g, 0.01 M) and N,N-dimethylamino-benzaldehyde (1.5 g 0.01 M) and a catalytic amount of KOH in 30 ml of distilled ethanol was stirred for about 24 h. The resulting mixture was concentrated to remove ethanol and then poured onto ice and neutralized with diluted acetic acid. The resultant solid was filtered, dried and purified by column chromatography using 1:1 v/v mixture of ethyl acetate and petroleum ether. Crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone solution (yield: 60%). M.p.: 421–423 K.