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(2E)-1-(2,4-Dimethyl-quinolin-3-yl)-3-phenyl-prop-2-en-1-one.

ABSTRACT: Two independent mol-ecules comprise the asymmetric unit of the title compound, C20H17NO, which differ in the orientation of the terminal phenyl ring with respect to the quinoline ring [the dihedral angles are 75.72?(11) and 84.53?(12)° for the two mol-ecules]. The conformation about each of the ethyl-ene bonds [1.329?(3) and 1.318?(3)?Å] is E. The crystal structure features a combination of C-H?N, C-H?? and ?-? contacts [inter-centroid between the phenyl ring and the quinoline benzene ring is 3.6024?(19)?Å], generating a three-dimensional network.

SUBMITTER: Prasath R

PROVIDER: S-EPMC3588443 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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(2E)-1-(2,4-Dimethyl-quinolin-3-yl)-3-phenyl-prop-2-en-1-one.

Prasath R R Bhavana P P Ng Seik Weng SW Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20130223 Pt 3

Two independent mol-ecules comprise the asymmetric unit of the title compound, C20H17NO, which differ in the orientation of the terminal phenyl ring with respect to the quinoline ring [the dihedral angles are 75.72 (11) and 84.53 (12)° for the two mol-ecules]. The conformation about each of the ethyl-ene bonds [1.329 (3) and 1.318 (3) Å] is E. The crystal structure features a combination of C-H⋯N, C-H⋯π and π-π contacts [inter-centroid between the phenyl ring and the quinoline benzene ring is 3. ...[more]

PMID: 23476600

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(2E)-1-(2,4-Dimethyl-quinolin-3-yl)-3-(thio-phen-2-yl)prop-2-en-1-one.

Project description:Two independent but virtually identical mol-ecules comprise the asymmetric unit in the title compound, C(18)H(15)NOS. With reference to the quinolin-3-yl group, the 3-(thio-phen-2-yl)prop-2-en-1-one residue is almost perpendicular, with all but the carbonyl O atom lying to one side of the plane. This conformation is reflected by the C-C-C-C torsion angles of -102.2 (3) and 81.1 (3)° in the two independent mol-ecules. The dihedral angle formed between the 13 non-H atoms directly associated with the quinolin-3-yl group and the thio-phen-2-yl ring is 87.70 (11)° [83.85 (10)° for the second independent mol-ecule]. The presence of C-H⋯O, C-H⋯N and π-π inter-actions [centroid-centroid distance = 3.5590 (12) Å] lead to supra-molecular chains along the c-axis direction. These are connected along the a-axis direction by C-H⋯π inter-actions. The resultant supra-molecular layers stack along the b axis.

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(2E)-3-(4-Chloro-phen-yl)-1-(2,4-dimethyl-quinolin-3-yl)prop-2-en-1-one.

Project description:Two independent mol-ecules comprise the asymmetric unit of the title compound, C(20)H(16)ClNO, which differ in the orientation of the chalcone residue with respect to the quinoline ring [the C-C-C(=O)-C torsion angles are 69.5?(2) and 86.0?(2)°]. The configuration about each of the ethyl-ene bonds [1.342?(2) and 1.338?(2)?Å] is E. The three-dimensional crystal structure is stabilized by a combination of C-H?O, C-H?N, C-H?? inter-actions and ?-? contacts between the independent mol-ecules [Cg(C(6) of quinoline)?Cg(C(6) of quinoline) = 3.6719?(11)?Å].

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(2E)-1-(6-Chloro-2-methyl-4-phenyl-quinolin-3-yl)-3-phenyl-prop-2-en-1-one.

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(2E)-3-(6-Chloro-2-meth-oxy-quinolin-3-yl)-1-(2,4-di-methyl-quinolin-3-yl)prop-2-en-1-one.

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(E)-1-(2,4-Dimethyl-quinolin-3-yl)-3-(4-methyl-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(21)H(19)NO, there are two mol-ecules in the asymmetric unit (Z' = 2). There are π-π inter-actions between these two mol-ecules [centroid-centroid distance = 3.678 (2) Å], as well as a weak C-H⋯O inter-action. The conformation adopted by the two mol-ecules is such that the quinoline mean plane and the benzene ring are almost perpendicular [89.04 (5) and 76.89 (4)°]. In each mol-ecule, the methyl group of the tolyl ring is disordered over two conformations, with occupancy ratios of 0.56 (3):0.44 (3) and 0.65 (3):0.35 (3).

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(2E)-3-(2-Chloro-benzo[h]quinolin-3-yl)-1-(2-methyl-4-phenyl-quinolin-3-yl)prop-2-en-1-one.

Project description:In the title compound, C32H21ClN2O, an almost planar (r.m.s. deviation = 0.033?Å) prop-2-en-1-one bridge links quinolinyl and benzoquinolinyl residues; the latter are twisted out of the plane of the bridge [dihedral angles = 75.94?(5) and 20.20?(5)°, respectively]. In the crystal, a three-dimensional architecture arises as a result of C-H?O, C-H?? and ?-? [centroid-centroid distances involving pyridine rings = 3.5806?(7)-3.7537?(7)?Å] interactions.

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(2E)-3-(4-Methyl-phen-yl)-1-(2-methyl-4-phenyl-quinolin-3-yl)prop-2-en-1-one monohydrate.

Project description:The title hydrate, C(26)H(21)NO·H(2)O, exhibits significant twists of the benzene ring [dihedral angle = 87.24?(6)°] and chalcone residue [C-C-C-C torsion angle = -94.46?(17)°] out of the plane through the quinoline ring system. The conformation about the C=C bond [1.341?(2)?Å] is E. The solvent water mol-ecule forms hydrogen bonds to carbonyl O and quinoline N atoms derived from two mol-ecules and through the application of a centre of inversion, a 16-membered {?HOH?OC(3)N}(2) synthon is formed to stabilize the resulting tetra-meric (two organic mol-ecules plus two water mol-ecules) aggregate. These are connected into a two-dimensional array via two C-H?O contacts, also involving the water mol-ecule. The layers stack along the c axis, being linked by C-H?? inter-actions.

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(2E)-1-(2-Methyl-4-phenyl-quinolin-3-yl)-3-(3-methyl-thio-phen-2-yl)prop-2-en-1-one.

Project description: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 mol-ecule has an L-shape. The conformation about the ethyl-ene bond [1.340?(2)?Å] is E. In the crystal, a supra-molecular chain with the shape of a square rod aligned along the b-axis direction is sustained by C-H?? inter-actions, the ?-systems being the heterocyclic rings.

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(2E)-1-(6-Chloro-2-methyl-4-phenyl-quinolin-3-yl)-3-(4-chloro-phen-yl)prop-2-en-1-one.

Project description:Two independent mol-ecules comprise the asymmetric unit of the title chalcone, C(25)H(17)Cl(2)NO, and while each has an E configuration about the ethyl-ene double bond, they differ in the relative orientations of the carbonyl and ethyl-ene double bonds within the prop-2-en-1-one residues, i.e. anti and syn. For each mol-ecule, the benzene [dihedral angles = 71.04 (9) and 73.34 (12)°] and prop-2-en-1-one [C-C-C-O = 91.2 (2) and -119.1 (3)°] substituents are twisted out of the plane of the quinoline moiety to which they are attached. The crystal structure is stabilized by C-H⋯π and π-π [Cg(quinoline)⋯Cg(quinoline) = 3.7809 (12) and 3.8446 (11) Å] inter-actions.

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