TY - JOUR
T1 - Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodophenyl)-1- (4-iodophenyl)prop-2-en-1-one
AU - Spruce, Kieran
AU - Hall, Charlie
AU - Potticary, Jason L
AU - Pridmore, Natalie E
AU - Cremeens, Matthew
AU - D'Ambrusco, Gemma
AU - Matsumoto, Masaomi
AU - Warren, Gabrielle
AU - Warren, Stephen
AU - Hall, Simon R
PY - 2020/1/1
Y1 - 2020/1/1
N2 - The molecular structure of the title compound, C15H10I2O, consists of two iodine substituted rings, one para-substituted and the other meta-substituted where both rings are linked through a prop-2-en-1-one spacer. The mean planes of the 3-iodophenyl and the 4-iodophenyl groups within the crystal are twisted by 46.92o. Calculated electrostatic surfaces show the presences of σ-holes on both substituted iodines, causing an interaction which is stronger than expected intermolecular interactions. It is seen in the fingerprint plots of the Hirshfeld surface analysis that the distance between iodine atoms is shorter than expected. Type II halogen bonding causes layering of substituted chalcone molecules with periodic iodine channels throughout the crystal parallel to [001]. The crystal structure is stabilized by weak intermolecular C···H interactions along [001]. Hirshfeld surface analysis showed that the most significant contacts are C···H/H···C (31.9%), followed by H···H (21.4%), I···H/H···I (18.4%). I···I (14.5%), O···H/H···O (8.1%).
AB - The molecular structure of the title compound, C15H10I2O, consists of two iodine substituted rings, one para-substituted and the other meta-substituted where both rings are linked through a prop-2-en-1-one spacer. The mean planes of the 3-iodophenyl and the 4-iodophenyl groups within the crystal are twisted by 46.92o. Calculated electrostatic surfaces show the presences of σ-holes on both substituted iodines, causing an interaction which is stronger than expected intermolecular interactions. It is seen in the fingerprint plots of the Hirshfeld surface analysis that the distance between iodine atoms is shorter than expected. Type II halogen bonding causes layering of substituted chalcone molecules with periodic iodine channels throughout the crystal parallel to [001]. The crystal structure is stabilized by weak intermolecular C···H interactions along [001]. Hirshfeld surface analysis showed that the most significant contacts are C···H/H···C (31.9%), followed by H···H (21.4%), I···H/H···I (18.4%). I···I (14.5%), O···H/H···O (8.1%).
UR - https://www.scopus.com/pages/publications/85077679359
U2 - 10.1107/S2056989019016402
DO - 10.1107/S2056989019016402
M3 - Article (Academic Journal)
C2 - 31921455
SN - 2056-9890
VL - 76
SP - 72
EP - 76
JO - Acta Crystallographica Section E: Crystallographic Communications
JF - Acta Crystallographica Section E: Crystallographic Communications
IS - 1
ER -