Premium
Crystal and molecular structure of 2,6‐bis(4‐fluorobenzylidene)cyclohexanone
Author(s) -
Ompraba G.,
Rafi Z. A.,
Yogavel M.,
Velmurugan D.,
Sekar K.,
Karthikeyan E.,
Perumal S.,
Choudhury A. R.,
Guru Row T. N.
Publication year - 2003
Publication title -
crystal research and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.377
H-Index - 64
eISSN - 1521-4079
pISSN - 0232-1300
DOI - 10.1002/crat.200310101
Subject(s) - triclinic crystal system , chemistry , van der waals force , steric effects , crystallography , ring (chemistry) , molecule , hydrogen bond , cyclohexanone , crystal (programming language) , crystal structure , bond length , cyclohexane conformation , van der waals radius , stereochemistry , catalysis , organic chemistry , computer science , programming language
The title compound, C 20 H 16 F 2 O, crystallizes in triclinic system with $ {\rm P} \bar1 $ space group and the unit cell parameters are: a = 9.700(5), b = 11.834(6), c = 14.315(7) Å, α = 78.464(9), β = 74.394(8), γ = 86.186(9)°, V = 1551.0(1) Å 3 and Z = 4. The final R‐factor is 4.8%. The cyclohexanone ring adopts a sofa conformation. The different ways of adjusting to steric repulsion results in significant differences between molecule A and B with respect to torsion angles. The steric repulsion between the aromatic groups and hydrogen atoms on the cyclohexanone ring causes increase of the values of bond angles at the C atoms joining the rings and rotation of the corresponding bond, at the expense of conjugation energy of the system. In addition to the van der Waals interactions, C‐H…O, C‐H…F and C‐H…π interactions stabilize the molecular packing. (© 2003 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim)