Crystal and molecular structure of diphenyl sulphone, 4,4′-difluorodiphenyl sulphone and 3,3′-dinitro-4,4′-difluorodiphenyl sulphone

Abstract

The crystal and molecular structures of diphenyl sulphone (A), 4,4′-difluorodiphenyl sulphone (B) and 3,3′-dinitro-4,4′-difluorodiphenyl sulphone (C) have been determined from three-dimensional MoKα diffractometer data. Each molecule crystallizes in the monoclinic space groupP21/c with cell dimensionsa = 12.225(4),b = 7.830(2),c = 11.328(2) A, β = 98 °19′(2);a = 8.255(3),b= 13.062(3),c = 10.135(2) A, β = 99 ° 31′(2) anda = 14.736 (4),b = 8.145(2),c= 14.626(3) A, β= 129°8′(2), respectively. The structures were solved by Patterson and Fourier techniques and refined by the method of least squares toR-factors of 3.8% over 1798 reflections, 6.3% over 1834 reflections and 5.4% over 2185 reflections forA,B andC, respectively. The dimensions of the sulphone group are similar in each molecule; the S—C bond lengths range from 1.764(3) to 1.775(3) A, and the S—O bond lengths from 1.432(3) to 1.439(3) A. The dihedral angles between the aromatic rings and the S—S—C planes lie between 72,6 and 88.9 °, compared with the value of 90 ° predicted for maximum conjugation between the sulphone group and the aromatic ring. Intermolecular H―O contacts of 2.37 A suggest possible C—H—O type hydrogen bonds joining the molecules of 4,4′-difluorodiphenyl sulphone into dimers and the molecules of 3,3′-dinitro-4,4′-difluorodiphenyl sulphone into chains.