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Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo-phen-yl)-1-(4-iodo-phen-yl)prop-2-en-1-one.

ABSTRACT: The title compound, C15H10I2O, is a halogenated chalcone formed from two iodine substituted rings, one para-substituted and the other meta-substituted, linked through a prop-2-en-1-one spacer. In the mol-ecule, the mean planes of the 3-iodo-phenyl and the 4-iodo-phenyl groups are twisted by 46.51 (15)°. The calculated electrostatic potential surfaces show the presence of σ-holes on both substituted iodines. In the crystal, the mol-ecules are linked through type II halogen bonds, forming a sheet structure parallel to the bc plane. Between the sheets, weak inter-molecular C-H⋯π inter-actions are observed. Hirshfeld surface analysis showed that the most significant contacts in the structure are C⋯H/H⋯C (31.9%), followed by H⋯H (21.4%), I⋯H/H⋯I (18.4%). I⋯I (14.5%) and O⋯H/H⋯O (8.1%).

SUBMITTER: Spruce KJ

PROVIDER: S-EPMC6944092 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluoro-phen-yl)prop-2-en-1-one: crystal structure and Hirshfeld surface analysis.

Project description:In the title compound, C23H14ClFO, the enone moiety adopts an E conformation. The dihedral angle between the benzene and anthracene ring is 63.42?(8)° and an intra-molecular C-H?F hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are arranged into centrosymmetric dimers via pairs of C-H?F hydrogen bonds. The crystal structure also features C-H?? and ?-? inter-actions. Hirshfeld surface analysis was used to confirm the existence of inter-molecular inter-actions.

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

Project description:In the title compound, C15H10BrFO, the mol-ecular structure consists of a 3-bromo-phenyl ring and a 4-fluoro-phenyl ring linked via a prop-2-en-1-one spacer. The 3-bromophenyl and 4-fluorophenyl rings make a dihedral angle of 48.90?(15)°. The mol-ecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. In the crystal, mol-ecules are linked by C-H?? inter-actions between the bromo-phenyl and fluoro-phenyl rings of mol-ecules, resulting in a two-dimensional layered structure parallel to the ab plane. The mol-ecular packing is stabilized by weak Br?H and F?H contacts, one of which is on the one side of each layer, and the second is on the other. The inter-molecular inter-actions in the crystal packing were further analysed using Hirshfeld surface analysis, which indicates that the most significant contacts are Cl?H/H?Cl (20.8%), followed by C?H/H?C (31.1%), H?H (21.7%), Br?H/H?Br (14.2%), F?H/H?F (9.8%), O?H/H?O (9.7%).

| S-EPMC6362636 | biostudies-literature

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.

Project description: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.

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

Project description:The asymmetric unit of the title halogenated chalcone derivative, C15H10BrFO, contains two independent mol-ecules, both adopting an s-cis configuration with respect to the C=O and C=C bonds. In the crystal, centrosymmetrically related mol-ecules are linked into dimers via inter-molecular hydrogen bonds, forming rings with R 1 2(6), R 2 2(10) and R 2 2(14) graph-set motifs. The dimers are further connected by C-H⋯O inter-actions into chains parallel to [001]. A Hirshfeld surface analysis suggests that the most significant contribution to the crystal packing is by H⋯H contacts (26.3%). Calculations performed on the optimized structure obtained using density functional theory (DFT) at B3LYP with the 6-311 G++(d,p) basis set reveal that the HOMO-LUMO energy gap is 4.12 eV, indicating the suitability of this crystal for optoelectronic and biological applications. The nucleophilic and electrophilic binding site regions are elucidated using the mol-ecular electrostatic potential (MEP).

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Crystal structure and Hirshfeld surface analysis of (E)-3-(2-chloro-4-fluoro-phen-yl)-1-(2,5-di-chloro-thio-phen-3-yl)prop-2-en-1-one.

Project description:In the title chalcone-thio-phene derivative, C13H6Cl3FOS, the aromatic rings are inclined to one another by 12.9?(2)°, and the thio-phene ring is affected by ?-conjugation. In the crystal, mol-ecules are linked by C-H?F hydrogen bonds, forming an R22(8) ring motif. A Hirshfeld surface analysis was conducted to verify the contribution of the different inter-molecular inter-actions. The shape-index surface clearly shows that the two sides of the mol-ecules are involved in the same contacts with neighbouring mol-ecules and the curvedness plots show flat surface patches characteristic of planar stacking.

| S-EPMC6073002 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-3-(2-chloro-6-fluoro-phen-yl)-1-(3-fluoro-4-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title chalcone derivative, C16H11ClF2O2, the enone group adopts an E conformation. The dihedral angle between the benzene rings is 0.47?(9)° and an intra-molecular C-H?F hydrogen bond closes an S(6) ring. In the crystal, mol-ecules are linked into a three-dimensional network by C-H?O hydrogen bonds and aromatic ?-? stacking inter-actions are also observed [centroid-centroid separation = 3.5629?(18)?Å]. The inter-molecular inter-actions in the crystal structure were qu-anti-fied and analysed using Hirshfeld surface analysis.

| S-EPMC4908511 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-3-(2-chloro-phen-yl)-1-(2,5-di-chloro-thio-phen-3-yl)prop-2-en-1-one.

Project description:The mol-ecular structure of the title compound, C13H7Cl3OS, consists of a 2,5- di-chloro-thio-phene ring and a 2-chloro-phenyl ring linked via a prop-2-en-1-one spacer. The dihedral angle between the 2,5-di-chloro-thio-phene and 2-chloro-phenyl rings is 9.69?(12)°. The mol-ecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The mol-ecular conformation is stabilized by two intra-molecular C-H?Cl contacts and one intra-molecular C-H?O contact, forming S(5)S(5)S(6) ring motifs. In the crystal, the mol-ecules are linked along the a-axis direction through van der Waals forces and along the b axis by face-to-face ?-stacking between the thio-phene rings and between the benzene rings of neighbouring mol-ecules, forming corrugated sheets lying parallel to the bc plane. The inter-molecular inter-actions in the crystal packing were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are Cl?H/ H?Cl (28.6%), followed by C?H/H?C (11.9%), C?C (11.1%), H?H (11.0%), Cl?Cl (8.1%), O?H/H?O (8.0%) and S?H/H?S (6.6%).

| S-EPMC6362645 | biostudies-literature

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

Project description:In title compound, C17H15ClO3, the dihedral angle between the benzene and chloro-phenyl rings is 18.46 (7)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen contacts, enclosing an R22(14) ring motif, and by a further C-H⋯O hydrogen contact, forming a two-dimensional supra-molecular structure extending along the direction parallel to the ac plane. 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 36.2% of the surface.

| S-EPMC6038638 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of a bromo-chalcone: (E)-1-(3-bromo-phen-yl)-3-(2,6-di-chloro-phen-yl)prop-2-en-1-one.

Project description:In the title chalcone derivative, C15H9BrCl2O, the aryl rings are inclined to each by 14.49?(17)°, and the configuration about the C=C bond is E. There is a short intra-molecular C-H?Cl contact present resulting in the formation of an S(6) ring motif. In the crystal, the shortest inter-molecular contacts are Cl?O contacts [3.173?(3)?Å] that link the mol-ecules to form a 21 helix propagating along the b-axis direction. The helices stack up the short crystallographic a axis, and are linked by offset ?-? inter-actions [inter-centroid distance = 3.983?(1)?Å], forming layers lying parallel to the ab plane. A qu-anti-fication of the inter-molecular contacts in the crystal were estimated using Hirshfeld surface analysis and two-dimensional fingerprint plots.

| S-EPMC6362637 | biostudies-literature

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

Project description:The mol-ecular structure of the title compound, C17H14ClFO3, consists of a 4-chloro-3-fluoro-phenyl ring and a 3,4-di-meth-oxy-phenyl ring linked via a prop-2-en-1-one spacer. The mol-ecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The F and H atoms at the meta positions of the 4-chloro-3-fluoro-phenyl ring are disordered over two orientations, with an occupancy ratio of 0.785?(3):0.215?(3). In the crystal, mol-ecules are linked via pairs of C-H?O inter-actions with an R 2 2(14) ring motif, forming inversion dimers. The dimers are linked into a tape structure running along [10] by a C-H?? inter-action. The inter-molecular contacts in the crystal were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are H?H (25.0%), followed by C?H/H?C (20.6%), O?H/H?O (15.6%), Cl?H/H?Cl (10.7%), F?H/H?F (10.4%), F?C/C?F (7.2%) and C?C (3.0%).

| S-EPMC6659344 | biostudies-literature

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