Crystal structure of an orthorhombic form of 1,2-bis(phenylsulfonyl)ethane at 86 K

Abstract

The crystal structure of an orthorhombic form of 1,2-bis-(phenylsulfonyl)ethane, C14H14O4S2, was studied by X-ray diffraction at 86 K. The space group is Pnah, a = 24.249(1) Ä, ft = 11.079(1) Ä, c = 5.257(1) Ä, and Z = 4. Two equivalent sets of intensities were collected to a maximum (sin0)/A = 0.904 A"' with MoÄa radiation. The data were corrected for absorption, scan truncation, extinction and multiple diffraction in addition to the routinely applied corrections before the final averaging. The structure was solved by Patterson methods, and leastsquares refinements were carried out within different shells of reciprocal Space. With all data, 3856 F", R is 0.027. The parameters obtained with (sin0)/A > 0.60 Ä~' give the best description of the structure {R = 0.030, 2481 F"), and a correction for rigid-body motion was applied to the two S-phenyl fragments. Relative to the values from the refmement with all data, the uncorrected aromatic C -C distances are longer by an average of 0.0042 Ä. All S -C bonds are in good agreement with the mean values for aromatic sulfones. One phenyl ring is in an anisotropic environment which causes rather large variations in the atomic displacement parameters and differences between pairs of bonds over the 1,4-diagonal. The other ring has almost exact C2" symmetry. The sequence C -C -S -C(phenyl) is oriented trans, compared to the gauche arrangement in the monoclinic form. The molecular packing is very different in the monoclinic and the orthorhombic forms.

4-Fluoro-3-nitrophenyl methyl sulfone

“…1. Bond lengths and angles are not unusual and compare well with those observed in other analogues (Podlaha et al, 1986;Julia et al, 1986;Hauback & Mo, 1990;Li et al, 2003;Guo & Yuan, 2005). The S O bond lengths within the SO 2 group are almost equal, with an average value of 1.4266 (19) Å .…”

4-Chloro-3-nitrophenyl methyl sulfone

“…1. Bond lengths and angles agree well with those observed in similar compounds (Podlaha et al, 1986;Julia et al, 1986;Hauback & Mo, 1990;Li et al, 2003;Guo & Yuan, 2005). The S O bond lengths within the SO 2 group are not significantly different, with an average value of 1.4352 (18) Å .…”

1-Benzenesulfonyl-5-chloro-2,4-dimethoxybenzene

“…For sulfone atom S1, formally S VI , the S-C and S O bond lengths and the O S O and C-S-C angles are all in normal ranges (Table 1), and compare well with those observed in other related compounds (e.g. Podlaha et al, 1986;Julia et al, 1986;Mo & Berg, 1982;Hauback & Mo, 1990). Least-squares plane calculations show that the dihedral angle between the phenyl (C1-C6) and benzene (C7-C12) planes is 73.0 (2) , and that atoms O3 and O4 are almost coplanar with the benzene ring.…”