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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.

ABSTRACT: 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.

SUBMITTER: Prasath R

PROVIDER: S-EPMC3588408 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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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.

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

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-mo ...[more]

PMID: 23476599

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

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Project description:The title hydrate, C(27)H(23)NO(2)·H(2)O, features an almost planar quinoline residue (r.m.s. deviation = 0.015?Å) with the benzene [dihedral angle = 63.80?(7) °] and chalcone [C-C-C-O torsion angle = -103.38?(18)°] substituents twisted significantly out of its plane. The configuration about the C=C bond [1.340?(2)?Å] is E. In the crystal, mol-ecules related by the 2(1) symmetry operation are linked along the b axis via water mol-ecules that form O-H?O(c) and O-H?N(q) hydrogen bonds (c = carbonyl and q = quinoline). A C-H?O inter-action also occurs.

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

Project description: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.

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

Project description:The crystal structure of the title compound, C(25)H(18)ClNO, shows that the mol-ecules are isolated and not involved in inter-molecular C-H⋯O or C-H⋯Cl inter-actions. However, the phenyl and quinoline rings are involved in π-π inter-actions [centroid-centroid distance = 3.8829 (9) Å].

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Crystal structure of (2E)-3-[4-(di-methyl-amino)-phen-yl]-1-(thio-phen-2-yl)prop-2-en-1-one.

Project description:The equimolar reaction between 4-(di-methyl-amino)-benzaldehyde and 2-acetyl-thio-phene in basic ethano-lic solution yields the title compound, C15H15NOS, whose mol-ecular structure matches the asymmetric unit. The mol-ecule is not planar, the dihedral angle between the aromatic and the thio-phene rings being 11.4?(2)°. In the crystal, mol-ecules are linked by C-H?O and weak C-H?S inter-actions along [100], forming R22 (8) rings, and by weak C-H?O inter-actions along [010], forming chains with a C(6) graph-set motif. In addition, mol-ecules are connected into centrosymmetric dimers by weak C-H?? inter-actions, as indicated by the Hirshfeld surface analysis. The most important contributions for the crystal structure are the H?H (46.50%) and H?C (23.40%) inter-actions. The crystal packing resembles a herringbone arrangement when viewed along [100]. A mol-ecular docking calculation of the title compound with the neuraminidase enzyme was carried out. The enzyme shows (ASN263)N-H?O, (PRO245)C-H?Cg(thio-phene ring) and (AGR287)C-H?N inter-molecular inter-actions with the title compound. The crystal structure was refined as a two-component twin with a fractional contribution to the minor domain of 0.0181?(8).

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(2E)-3-(2-Chloro-7-methyl-quinolin-3-yl)-1-(6-chloro-2-methyl-4-phenyl-quinolin-3-yl)prop-2-en-1-one ethanol monosolvate.

Project description:In the title ethanol solvate, C29H20Cl2N2O·C2H5OH, the quinolinyl residues form a dihedral angle of 46.41?(4)° with each other, and each is inclined [Cp-C-C=O and C=C-C-Cp (p = pyridyl) torsion angles = 54.8?(2) and 144.44?(19)°, respectively] with respect to the almost planar bridging prop-2-en-1-one residue [O=C-C=C torsion angle = -4.1?(3)°]. The ethanol solvent mol-ecule is disordered over two positions of equal occupancy and is located close to a centre of inversion. These mol-ecules reside in cavities defined by the organic mol-ecules, which are connected into a three-dimensional architecture by C-H?Cl, C-H?O and C-H?N inter-actions, as well as ?-? contacts [inter-centroid distances = 3.5853?(10) and 3.8268?(11)?Å], each involving pyridyl rings.

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