H. Levi, R. Doedens
Aug 15, 1980
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0
Influential Citations
4
Citations
Journal
Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry
Abstract
Aeta Cryst. (1980). B36, 1959-1961 3-Bromo-2,5-diphenyl- 1,4-dithiin l,l-Dioxide Be HUGO A. LEVI AND ROBERT J. DOEDENS Department of Chemistry, University of California, Irvine, California 92717, USA (Received 14 November 1979; accepted 25 February 1980) Abstract. C I 6 H I I B r O 2 S 2 , triclinic P i , a = 9-174 (1), b = 9.239 (1), c = 9.367 (1)A, a = 71.68 (1), fl = 89.29 (1), y = 85.04 (1) ° , V = 750.8 (2) A 3, Z = 2, D m = 1.680 (flotation), D c = 1.676 Mg m -3. The molecule has a boat conformation. The mean S - C distances and the C - S - C angles at the two S atoms are similar. The molecule is more nearly planar than other 1,4-dithiin derivatives. Introduction. The title compound was first obtained as a product of the oxidation of 3-bromo-2,5-diphenyl- 1,4-dithiin with H20 2 (Parham, Nicholson & Traynelis, 1956) or with peracetic acid (Szmant & Alfonso, 1957), although the regiochemistry of the oxidation (i.e. whether the Br was at the 2 or 3 position of the ring) was not established. More recently (Levi, 1979), products believed to be the 2-bromo and 3-bromo isomers of this compound were prepared; however, spectroscopic data again provided no definitive basis for determining the identities of these isomers. Since this information was of importance in the interpre- tation of the chemistry of these molecules, and since no detailed structural data were available for any dithiin 1,l-dioxide, a crystal structure analysis was under- taken. Colorless crystals of the title compound were obtained by slow evaporation of a chloroform solution. The crystal used for all X-ray studies was a rectangular prism of dimensions 0.33 x 0.20 x 0.20 m m which had been cut from a larger crystal and mounted on a glass fiber. Data were collected with graphite-mono- chromatized Mo Ka radiation (J. = 0.71073 A) on a Syntex P21 automated diffractometer under the control of a Nova 1200 computer. Refined cell parameters (T = 295 K) were based upon the setting angles of 15 reflections with 30 ° 3 a ( F 2) and were used in subsequent calculations. Intensity statistics implied a centrosymmetric struc- ture. The structure solution was achieved in a straight- Table 1. Positional parameters and equivalent isotropic thermal parameters of the nonhydrogen atoms x Br S(I) S(2) O(1) C(1) C(2) C(3) C(4) C(5) C(6) C(7) C(8) C(9) C(10) C(11) C(12) C(13) C(14) C(15) C(16) y z Ueq (A 2) 0.045t * Throughout this paper, numbers in parentheses are estimated standard deviations in the least significant figures. I Ueq = ](U H + U22 + U33), where U, = principal mean-square thermal displacement. © 1980 International Union of Crystallography