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

ABSTRACT: 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.

SUBMITTER: Prasath R

PROVIDER: S-EPMC3200943 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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.

| S-EPMC3588443 | biostudies-literature

(2E)-1-(2,5-Dimethyl-thio-phen-3-yl)-3-(3-nitro-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(15)H(13)NO(3)S, the benzene ring and the five-membered heterocyclic ring are oriented at a dihedral angle of 12.00 (6)°. In the crystal, C-H⋯O inter-actions generate two types of cyclic motifs, R(2) (2)(14) and R(2) (2)(26), connecting the mol-ecules into tapes extending along [101]. In addition, there are π-π stacking inter-actions between the benzene and thio-phene rings with centroid-centroid distances of 3.7263 (14) and 3.7487 (14) Å.

| S-EPMC3238980 | biostudies-literature

(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].

| S-EPMC3099908 | biostudies-other

(2E)-3-(3,4-Dimeth-oxy-phen-yl)-1-(2,5-dimethyl-thio-phen-3-yl)prop-2-en-1-one.

Project description:The mol-ecule of the title compound, C(17)H(18)O(3)S, is essentially planar: the phenyl and thio-phene rings form a dihedral angle of 2.79?(10)° and they are inclined to the central propenone unit by 6.20?(15) and 4.78?(15)°, respectively. In the crystal, mol-ecules are connected into dimers via pairs of C-H?O inter-actions, generating R(2) (2)(14) motifs. ?-? stacking inter-actions between the thio-phene rings also occur, with a centroid-centroid distance of 3.8062?(12)?Å.

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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).

| S-EPMC3344610 | biostudies-literature

(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-(4-Amino-phen-yl)-3-(2,4-dichloro-phen-yl)prop-2-en-1-one.

Project description:The title compound, C(15)H(11)Cl(2)NO, is approximately planar (r.m.s. deviation = 0.062?Å) and contains a single C=C double bond in a trans (E) configuration. The crystal packing is stabilized by intermolecular N-H?N and N-H?O inter-molecular hydrogen bonding.

| S-EPMC3152147 | biostudies-literature

(2E)-1-(2,4-Dichloro-phen-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(18)H(16)Cl(2)O(4), the dihedral angle between the benzene rings is 82.40 (4)°. The meth-oxy groups at both meta positions of the 3,4,5-trimeth-oxy-phenyl ring are slightly twisted from the aromatic ring [C-O-C-C = -166.60 (8) and -6.18 (13)°], whereas the meth-oxy group at the para position is almost perpendicular [C-O-C-C = 112.08 (9)°]. The ketone O atom is connected to the 2,4-dichloro-phenyl group through a C(ar)-C(ar)-C-O (ar = aromatic) torsion angle of -116.43 (9)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into infinite chains along the b axis. The crystal structure also features C-H⋯π inter-actions.

| S-EPMC3344577 | biostudies-literature

(2E)-3-[4-(Dimethyl-amino)-phen-yl]-1-(4-fluoro-phen-yl)prop-2-en-1-one.

Project description:The mean planes of the two benzene rings in the title compound, C(17)H(16)FNO, are twisted slightly, making a dihedral angle of 7.8 (1)°. The prop-2-en-1-one group is also twisted slightly with a C-C-C-O torsion angle of -11.6 (3)°. In the crystal, weak inter-molecular C-H⋯O inter-actions link pairs of mol-ecules, forming centrosymmetric dimers.

| S-EPMC3051752 | biostudies-literature

(2E)-3-(2-Chloro-8-methyl-quinolin-3-yl)-1-(2,4-di-methyl-quinolin-3-yl)prop-2-en-1-one.

Project description:In the mol-ecule 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 Car-Car-C-C (ar = aromatic) torsion angles being 71.01?(17) and 20.6?(2)°. The crystal structure features phen-yl-carbonyl C-H?O inter-actions and ?-? inter-actions between centrosymmetrically related quinolinyl residues [3.5341?(10) and 3.8719?(9)?Å], which together lead to a three-dimensional architecture.

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