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

ABSTRACT: In the title compound, C(25)H(18)ClNO, the conformation about the C=C double bond is E. Significant twists are evident in the mol-ecule, with the benzene ring forming a dihedral angle of 53.92 (11)° with the quinolinyl residue. Further, the chalcone residue is approximately perpendicular to the quinolinyl residue [C(q)-C(q)-C(c)-O(c) torsion angle = -104.5 (3)°, where q = quinolinyl and c = chalcone]. In the crystal, the presence of C-H⋯O and C-H⋯π inter-actions leads to supra-molecular layers lying parallel to (02).

SUBMITTER: Viji AJ

PROVIDER: S-EPMC3006996 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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?? and ?-? [Cg(quinoline)?Cg(quinoline) = 3.7809?(12) and 3.8446?(11)?Å] inter-actions.

| S-EPMC3052117 | biostudies-literature

(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.

| S-EPMC3884470 | biostudies-literature

(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.

| S-EPMC3884436 | 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.

| S-EPMC3793770 | biostudies-literature

(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.

| S-EPMC3009190 | biostudies-literature

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

Project description:The mol-ecule of the title compound, C24H19ClN2O2, is bent, with the dihedral angle between the terminal quinoline ring systems being 63.30?(5)°. The quinolinyl residues are connected by an almost planar prop-2-en-1-one bridge (r.m.s. deviation = 0.022?Å), with the dihedral angles between this plane and the appended quinolinyl residues being 75.86?(7) and 38.54?(7)°. The C atom of the meth-oxy group is close to coplanar with its attached ring [deviation = 0.116?(2)?Å]. In the crystal, a three-dimensional architecture is constructed by meth-yl-carbonyl C-H?O inter-actions and ?-? inter-actions between centrosymmetrically related quinolinyl residues [centroid-to-centroid separations 3.5341?(10) and 3.8719?(9)?Å].

| S-EPMC3793769 | biostudies-literature

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

Project description:In the title compound, C29H21ClN2O, there is a twist in the bridging prop-2-en-1-one group [C=C-C=O torsion angle = 22.7?(2)°]. The quinolinyl residues form a dihedral angle of 86.92?(4)°, indicating an almost perpendicular relationship. In the crystal, supra-molecular layers in the bc plane are stabilized by C-H?? and ?-? inter-actions [centroid-centroid distance = 3.4947?(7)?Å].

| S-EPMC3793805 | biostudies-other

(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.

| S-EPMC3588408 | biostudies-literature

(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

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].

| S-EPMC3051952 | biostudies-literature

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