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Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-bromo-4-fluoro-phen-yl)-1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one.

ABSTRACT: In the mol-ecule of the title compound, C17H14BrFO3, the aromatic rings are tilted with respect to the enone bridge by 13.63 (14) and 4.27 (15)°, and form a dihedral angle 17.91 (17)°. In the crystal, centrosymmetrically related mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into dimeric units, forming rings of R22(14) graph-set motif. The dimers are further connected by weak C-H⋯O hydrogen inter-actions, forming layers parallel to (10). Hirshfeld surface analysis shows that van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 29.7% of the surface.

SUBMITTER: Sheshadri SN

PROVIDER: S-EPMC6072984 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structures of (2E)-1-(3-bromo-thio-phen-2-yl)-3-(2-meth-oxy-phen-yl)prop-2-en-1-one and (2E)-1-(3-bromo-thio-phen-2-yl)-3-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the mol-ecules of the title compounds, (2E)-1-(3-bromo-thio-phen-2-yl)-3-(2-meth-oxy-phen-yl)prop-2-en-1-one, C14H11BrO2S, (I), which crystallizes in the space group P-1 with four independent mol-ecules in the asymmetric unit (Z' = 8), and (2E)-1-(3-bromo-thio-phen-2-yl)-3-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one, C15H13BrO3S, (II), which crystallizes with Z' = 8 in the space group I2/a, the non-H atoms are nearly coplanar. The mol-ecules of (I) pack with inversion symmetry stacked diagonally along the a-axis direction. Weak C-H?Br intra-molecular inter-actions in each of the four mol-ecules in the asymmetric unit are observed. In (II), weak C-H?O, bifurcated three-center inter-molecular inter-actions forming dimers along with weak C-H?? and ?-? stacking inter-actions are observed, linking the mol-ecules into sheets along [001]. A weak C-H?Br intra-molecular inter-action is also present. There are no classical hydrogen bonds present in either structure.

| S-EPMC4571368 | biostudies-literature

(2E)-1-(2-Bromo-phen-yl)-3-(4-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(16)H(13)BrO(2), two benzene rings form a dihedral angle of 44.3?(9)°. In the crystal, weak inter-molecular C-H?O hydrogen bonds link the mol-ecules into chains propagating in [010]. The crystal packing also exhibits short Br?Br contacts of 3.4787?(8)?Å. A comparison of the DFT-optimized gas-phase mol-ecular geometry with that in the crystal structure revealed only small differences.

| S-EPMC3006708 | biostudies-literature

(E)-3-(3,4-Di-fluoro-phen-yl)-1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C17H14F2O3, the dihedral angle between the benzene rings is 20.56 (8)° and the H atoms at the central propenone group are trans configured. One of the F atoms is disordered over two positions (occupancy ratio 0.57:0.43) and was refined using a split model. In the crystal, the molecules are linked into centrosymmetrical dimers and are further connected into a three-dimensional network via weak C-H⋯O interactions.

| S-EPMC3685099 | biostudies-literature

(2E)-3-(3-Bromo-4-meth-oxy-phen-yl)-1-(4-methyl-phen-yl)prop-2-en-1-one.

Project description:The overall shape of the mol-ecule of the title compound, C(17)H(15)BrO(2), can be described by the dihedral angles between three planar fragments: 1-bromo-2-meth-oxy-phenyl ring [maximum deviation = 0.003 (2) Å], the central prop-2-en-1-one chain [maximum deviation = 0.005 (2) Å], and the methyl-phenyl ring [maximum deviation = 0.004 (2) Å]. The terminal planes are twisted by 10.37 (12)°, while the central plane is almost coplanar with the methyl-phenyl ring [3.30 (13)°], but the dihedral angle with the other phenyl ring is significantly larger [8.76 (16)°]. In the crystal, mol-ecules are linked into chains along [001] by three C-H⋯O hydrogen bonds. These chains inter-act with each other by means of weak π-π contacts [centroid-centroid distances = 3.73 (1) and 3.44 (1) Å]. An inter-molecular C-H⋯Br inter-action also occurs.

| S-EPMC3099759 | biostudies-literature

(2E)-1-(2,6-Dichloro-3-fluoro-phen-yl)-3-(4-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C(16)H(11)Cl(2)FO(2). The F atom equally populates both meta positions of the 6-dichloro-3-fluoro-phenyl ring in each mol-ecule, resulting in 0.5 occupancy for both the F and H atoms in these positions. The dihedral angle between the mean planes of the benzene rings are 77.5?(2) and 89.8?(8)°in the two mol-ecules. In the crystal, weak C-H?F and C-H?O inter-actions involving the half-occupied H and F atoms are observed. Weak ?-? stacking inter-actions [centroid-centroid distance = 3.150?(2)?Å] also contribute to the crystal stability.

| S-EPMC3344105 | biostudies-literature

(2E)-1-(2-Bromo-phen-yl)-3-(4-bromo-phen-yl)prop-2-en-1-one.

Project description:The title compound, C(15)H(10)Br(2)O, is a chalcone with 2-bromo-phenyl and 4-bromo-phenyl rings bonded to opposite sides of a propenone group. The dihedral angle between mean planes of the benzene rings is 71.3 (1)°. The angle between the mean plane of the prop-2-ene-1-one group and the mean planes of the 2-bromo-phenyl and 4-bromo-phenyl rings are 64.2 (9) and 71.3 (1)°, respectively. A weak inter-molecular C-H⋯O inter-action and two weak C-Br⋯π inter-actions are observed, which contribute to the stability of the crystal packing.

| S-EPMC3006939 | biostudies-literature

(2E)-3-(2-Fluoro-phen-yl)-1-(4-fluoro-phen-yl)prop-2-en-1-one.

Project description:In the title compouund, C(15)H(10)F(2)O, the mol-ecule exists in an E conformation with respect to the C=C bond [1.3382 (16) Å]. The dihedral angle between the fluoro-substituted benzene rings is 6.80 (6)° and the whole mol-ecule is roughly planar (r.m.s. deviation for the non-H atoms = 0.069 Å). In the crystal, mol-ecules are linked by C-H⋯F and C-H⋯O inter-actions into sheets lying parallel to the bc plane.

| S-EPMC3435684 | biostudies-literature

(2E)-3-(3-Bromo-4-meth-oxy-phen-yl)-1-(4-fluoro-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(16)H(12)BrFO(2), the dihedral angle between the aromatic rings is 23.75?(12)° and the dihedral angle between the prop-2-en-1-one fragment and the fluorobenzene ring is 20.9?(2)°. In the crystal, only van der Waals interactions occur.

| S-EPMC3089233 | biostudies-other

(2E)-1-(3-Bromo-phen-yl)-3-(6-meth-oxy-2-naphth-yl)prop-2-en-1-one.

Project description:In the title compound, C(20)H(15)BrO(2), the prop-2-en-1-one fragment is substanti-ally twisted [C-C-C-O = 23.0?(11)°]. The dihedral angle between the benzene and naphthalene rings is 44.28?(13)°. The only possible directional inter-actions in the crystal are weak C-H?? contacts, which generate (001) sheets.

| S-EPMC2983307 | biostudies-literature

(2E)-3-(3-Bromo-4-meth-oxy-phen-yl)-1-(pyridin-2-yl)prop-2-en-1-one.

Project description:The mean planes of the benzene and pyridine rings in the title compound, C(15)H(12)BrNO(2), are nearly coplanar, subtending an angle of 2.8 (8)°. The prop-2-en-1-one group is also in the plane of these rings with an N-C-C-O torsion angle of 179.6 (3)°. A weak C-H⋯Br inter-molecular inter-action contributes to the crystal packing, creating a chain-like structure along the a axis.

| S-EPMC3051466 | biostudies-literature

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