1. Name of contact person Dr M. Migaud, 2. E-mail address of contact person m.migaud@qub.ac.uk ; 3. Authors' names Marie E. Migaud,a Rupert C. Wilmouth,a Gareth J. Wayne,b Catherine Risley,c Simon J. Macdonaldb and Christopher J. Schofielda* 4. Name of the journal to which the paper has been or will be submitted J. Chem. Soc.; Chemical Communication 5. Compound name _6-methanesulfonyl-4,4-bis-allyl-4,6 dihydro-thieno [2,3-b] pyrrol-5-one 6. Compound synonym (drug name, brand name, etc.) 7. Formula _C13H15NO3S2 8. Formula weight _297.05 g/mol 9. Colour _colourless crystlas 10. Melting point (in K) _128oC Table 1. Crystal data and structure refinement for str81 . Identification code str81 Empirical formula C13 H15 N O3 S2 Formula weight 297.39 Temperature 150 K Wavelength 0.71069 Å Crystal system Trigonal Space group P 32 Unit cell dimensions a == 8.315(7) Å ?== 90° b == 8.315(3) Å ?== 90° c == 18.101(3) Å ? == 120° Volume 1083.8(5) Å3 Z 3 Density (calculated) 1.37 Mg/m3 Absorption coefficient 0.37 mm-1 F(000) 468.77 Crystal size 0.30 x 0.25 x 0.25 mm Theta range for data collection 0.00 to 26.57° Index ranges 0(h(10, -8(k(0, -22(l(22 Reflections collected 2978 Independent reflections 1365 [R(int) == 0.03] Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.91 and 0.91 Refinement method Full-matrix least-squares on F Data / parameters 1336 / 172 Goodness-of-fit on F2 1.0913 R indices (all data) R1 == 0.0456, wR2 == 0.0294 Extinction coefficient 109.544 Largest diff. peak and hole 0.31 and -0.37 e.Å-3 Table 2. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å2x 103) for str81. U(eq) is defined as one third the trace of the orthogonalized Uij tensor. x y z U(eq) S(1) 1325(1) 2473(1) 4446(1) 27 S(4) -2995(1) 711(1) 3462(1) 23 C(2) 751(5) 3122(4) 3628(2) 22 C(7) -4156(7) 1947(7) 3643(2) 48 C(8) -501(5) 3415(4) 2549(2) 21 C(10) 1554(4) 4948(5) 2567(2) 21 C(11) 2175(4) 4567(4) 3295(2) 22 C(12) 3849(5) 5250(5) 3706(2) 22 C(13) 3583(5) 4258(5) 4336(2) 26 C(14) 1625(5) 6840(5) 2523(2) 26 C(15) 647(5) 7185(5) 3148(2) 32 C(16) -690(8) 7557(8) 3077(3) 54 C(17) 2569(5) 4707(5) 1899(2) 29 C(18) 2511(6) 2884(7) 1878(2) 40 C(19) 3940(8) 2656(9) 1884(3) 61 N(3) -871(4) 2350(4) 3195(1) 26 O(5) -2704(4) -19(4) 4131(1) 34 O(6) -3829(4) -469(4) 2849(1) 39 O(9) -1640(3) 3159(4) 2081(1) 28 H(71) -5441 1125 3808 60 H(72) -3483 2913 4040 60 H(73) -4176 2639 3191 60 H(121) 5054 6335 3552 60 H(131) 4588 4523 4694 60 H(141) 2956 7848 2518 60 H(142) 1042 6894 2050 60 H(151) 1056 7131 3665 60 H(161) -1267 7781 3527 60 H(162) -1143 7651 2585 60 H(171) 3884 5718 1909 60 H(172) 1977 4846 1439 60 H(181) 1255 1722 1861 60 H(191) 5234 3796 1891 60 H(192) 3841 1425 1864 60 Table 3. Bond lengths [Å] and angles [°] for str81. S(1)-C(2) 1.724(3) S(1)-C(13) 1.726(4) S(4)-C(7) 1.757(4) S(4)-N(3) 1.674(3) S(4)-O(5) 1.428(3) S(4)-O(6) 1.413(3) C(2)-C(11) 1.336(5) C(2)-N(3) 1.407(4) C(7)-H(71) 0.984(5) C(7)-H(72) 1.012(5) C(7)-H(73) 1.006(4) C(8)-C(10) 1.539(4) C(8)-N(3) 1.405(4) C(8)-O(9) 1.208(4) C(10)-C(11) 1.505(4) C(10)-C(14) 1.547(5) C(10)-C(17) 1.544(4) C(11)-C(12) 1.423(4) C(12)-C(13) 1.360(5) C(12)-H(121) 0.996(3) C(13)-H(131) 0.990(3) C(14)-C(15) 1.503(5) C(14)-H(141) 1.000(3) C(14)-H(142) 0.996(3) C(15)-C(16) 1.301(6) C(15)-H(151) 1.003(3) C(16)-H(161) 1.009(5) C(16)-H(162) 0.985(4) C(17)-C(18) 1.493(6) C(17)-H(171) 0.992(4) C(17)-H(172) 1.004(3) C(18)-C(19) 1.293(6) C(18)-H(181) 1.008(5) C(19)-H(191) 1.018(7) C(19)-H(192) 0.985(6) C(2)-S(1)-C(13) 89.09(16) C(7)-S(4)-N(3) 104.02(19) C(7)-S(4)-O(5) 110.49(17) N(3)-S(4)-O(5) 104.91(14) C(7)-S(4)-O(6) 109.2(2) N(3)-S(4)-O(6) 106.86(15) O(5)-S(4)-O(6) 119.98(19) S(1)-C(2)-C(11) 114.2(2) S(1)-C(2)-N(3) 133.5(2) C(11)-C(2)-N(3) 112.1(3) S(4)-C(7)-H(71) 112.0(4) S(4)-C(7)-H(72) 110.4(3) H(71)-C(7)-H(72) 108.3(3) S(4)-C(7)-H(73) 110.8(3) H(71)-C(7)-H(73) 108.8(4) H(72)-C(7)-H(73) 106.5(5) C(10)-C(8)-N(3) 107.9(2) C(10)-C(8)-O(9) 127.5(3) N(3)-C(8)-O(9) 124.6(3) C(8)-C(10)-C(11) 101.5(2) C(8)-C(10)-C(14) 107.6(3) C(11)-C(10)-C(14) 114.6(3) C(8)-C(10)-C(17) 109.2(3) C(11)-C(10)-C(17) 113.0(3) C(14)-C(10)-C(17) 110.2(3) C(2)-C(11)-C(10) 109.9(3) C(2)-C(11)-C(12) 111.9(3) C(10)-C(11)-C(12) 138.1(3) C(11)-C(12)-C(13) 111.5(3) C(11)-C(12)-H(121) 123.8(3) C(13)-C(12)-H(121) 124.7(3) S(1)-C(13)-C(12) 113.3(2) S(1)-C(13)-H(131) 123.3(3) C(12)-C(13)-H(131) 123.3(3) C(10)-C(14)-C(15) 114.0(3) C(10)-C(14)-H(141) 108.5(3) C(15)-C(14)-H(141) 108.9(3) C(10)-C(14)-H(142) 108.6(3) C(15)-C(14)-H(142) 108.5(3) H(141)-C(14)-H(142) 108.3(3) C(14)-C(15)-C(16) 125.4(3) C(14)-C(15)-H(151) 117.7(3) C(16)-C(15)-H(151) 116.9(4) C(15)-C(16)-H(161) 120.4(4) C(15)-C(16)-H(162) 121.0(4) H(161)-C(16)-H(162) 118.6(5) C(10)-C(17)-C(18) 114.2(3) C(10)-C(17)-H(171) 108.5(3) C(18)-C(17)-H(171) 108.9(3) C(10)-C(17)-H(172) 107.7(3) C(18)-C(17)-H(172) 109.1(3) H(171)-C(17)-H(172) 108.3(3) C(17)-C(18)-C(19) 125.7(5) C(17)-C(18)-H(181) 117.8(4) C(19)-C(18)-H(181) 116.6(5) C(18)-C(19)-H(191) 118.9(5) C(18)-C(19)-H(192) 123.1(6) H(191)-C(19)-H(192) 117.9(5) S(4)-N(3)-C(2) 126.2(2) S(4)-N(3)-C(8) 124.3(2) C(2)-N(3)-C(8) 108.5(3) Table 4. Anisotropic displacement parameters (Å2x 103)for str81. The anisotropic displacement factor exponent takes the form: -2?2[ h2a*2U11 + ... + 2 h k a* b* U12 ] U11 U22 U33 U23 U13 U12 S(1) 31(1) 27(1) 19(1) 6(1) -4(1) 12(1) S(4) 18(1) 22(1) 22(1) 2(1) 5(1) 4(1) C(2) 23(2) 25(2) 14(1) -1(1) -6(1) 9(1) C(7) 56(3) 71(3) 33(2) 9(2) 16(2) 46(3) C(8) 23(2) 19(2) 18(1) -1(1) 0(1) 9(1) C(10) 16(2) 24(2) 18(1) 1(1) -3(1) 6(1) C(11) 22(2) 22(2) 21(1) 0(1) -1(1) 10(1) C(12) 21(2) 21(2) 25(2) 0(1) -4(1) 10(1) C(13) 25(2) 26(2) 28(2) -7(1) -11(1) 14(2) C(14) 24(2) 26(2) 25(2) 2(1) -7(1) 9(2) C(15) 37(2) 30(2) 28(2) -2(1) -9(1) 16(2) C(16) 61(3) 64(3) 53(3) -4(2) -6(2) 44(3) C(17) 26(2) 42(2) 19(2) 5(1) 3(1) 16(2) C(18) 48(2) 50(2) 27(2) -1(2) 8(2) 28(2) C(19) 74(4) 89(4) 47(3) 6(2) 12(2) 62(4) N(3) 21(1) 26(2) 18(1) 5(1) -1(1) 2(1) O(5) 29(1) 32(1) 28(1) 10(1) 7(1) 6(1) O(6) 25(1) 32(2) 37(1) -4(1) 0(1) -3(1) O(9) 23(1) 32(1) 21(1) 1(1) -7(1) 8(1) Experimentator: Dr Leigh H. Rees E-mail: Leigh.Rees@chem.ox.ac.uk Tel. +44 (0)1865 270832 Fax. +44 (0)1865 272690 Colourless crystals of str81 were grown by diffusion of 40-60 petroleum ether into an acetone solution. A single crystal having approximate dimensions of 0.25 x 0.25 x 0.30 mm was encased in perfluoropolyether oil and mounted atop a glass fibre. The fibre, secured in a goniometer head was then placed under a stream of cold nitrogen maintained at 150 K and data collected using a Enraf-Nonius DIP2000 Image Plate Diffractometer (graphite monochromator, X-ray radiation Mo K? ? == 0.71069 Å). A total of 30 'frames' of data were collected at 600 secs per frame affording an overall data collection time of ca. 5 hours and 2978 reflections. Data frames were processed using the programs DENZO1and SCALEPACK2 running on a Silicon Graphics Indy computer. The structure was solved using the program SIR973 and refined to a conventional R1 factor of 0.0456 using full-matrix least-squares on all F data [CRYSTALS]4. All non-hydrogen atoms were refined anisotropically and hydrogen atoms were included in calculated positions with isotropic thermal parameters. All calculations were carried out on a Pentium III personal computer. str81 crystallised in the trigonal space group P32 with one molecule in the asymmetric unit. Attached are thermal ellipsoid (40 % probability) diagrams along with a summary of crystallographic data and refinement details (Table 1) and bond distances and angles (Table 2). References 1 DENZO, Z. Otwinowski and W. Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods in Enzymology,276,1997 , 307-326; Ed Carter, C.W. & Sweet, R.M., Academic Press. 2 SCALEPACK, Z. Otwinowski and W. Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods in Enzymology,1997,276 , 307-326; Ed Carter, C.W. & Sweet, R.M., Academic Press. 3 SIR97 - A program for crystal structure solution. 4 CRYSTALS - D.J. Watkin, C.K. Prout, J.R. Carruthers and P.W. Better (1996), Issue 10. Chemical Crystallography Laboratory, OXFORD, UK