#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202328.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2202328
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1070
_journal_page_last  o1072
_publ_section_title
;
(1'S,2R,3R)-3-(1'-tert-Butyldimethylsilyloxy-1'-phenylmethyl)-
2-(4''-methylphenylthio)-2-nitrooxirane
;
loop_
_publ_author_name
  'Clegg, William' .
  'Elsegood, Mark R. J.'
_chemical_formula_moiety  'C22 H29 N O4 S Si'
_chemical_formula_sum  'C22 H29 N O4 S Si'
_chemical_formula_iupac  'C22 H29 N O4 S Si'
_chemical_formula_weight  431.61
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  10.0904(12)
_cell_length_b  8.9428(11)
_cell_length_c  13.1503(16)
_cell_angle_alpha  90.00
_cell_angle_beta  95.531(3)
_cell_angle_gamma  90.00
_cell_volume  1181.1(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  160(2)
_exptl_crystal_density_diffrn  1.214
_diffrn_ambient_temperature  160(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  O1 0.33416(13) 0.41659(15) 0.35992(10) 0.0359(3) Uani d . 1 . . O
  C1 0.21246(18) 0.4483(2) 0.30530(14) 0.0326(4) Uani d . 1 . . C
  C2 0.28023(18) 0.3071(2) 0.28598(13) 0.0319(4) Uani d . 1 . . C
  H2 0.2415 0.2155 0.3151 0.038 Uiso calc R 1 . . H
  N1 0.09616(18) 0.4315(2) 0.37214(14) 0.0439(4) Uani d . 1 . . N
  O2 -0.00947(16) 0.4871(2) 0.34073(16) 0.0679(5) Uani d . 1 . . O
  O3 0.11668(17) 0.3605(2) 0.45007(13) 0.0711(6) Uani d . 1 . . O
  C3 0.35306(18) 0.2825(2) 0.19186(14) 0.0325(4) Uani d . 1 . . C
  H3 0.3772 0.3812 0.1631 0.039 Uiso calc R 1 . . H
  C4 0.26396(17) 0.1982(2) 0.11369(14) 0.0318(4) Uani d . 1 . . C
  C5 0.24227(19) 0.0459(2) 0.12654(16) 0.0381(4) Uani d . 1 . . C
  H5 0.2863 -0.0049 0.1836 0.046 Uiso calc R 1 . . H
  C6 0.1573(2) -0.0317(2) 0.05692(16) 0.0430(5) Uani d . 1 . . C
  H6 0.1427 -0.1354 0.0667 0.052 Uiso calc R 1 . . H
  C7 0.0935(2) 0.0399(3) -0.02632(17) 0.0421(5) Uani d . 1 . . C
  H7 0.0349 -0.0143 -0.0738 0.051 Uiso calc R 1 . . H
  C8 0.1146(2) 0.1905(3) -0.04091(16) 0.0418(5) Uani d . 1 . . C
  H8 0.0716 0.2402 -0.0988 0.050 Uiso calc R 1 . . H
  C9 0.19913(19) 0.2689(2) 0.02950(15) 0.0373(5) Uani d . 1 . . C
  H9 0.2127 0.3728 0.0198 0.045 Uiso calc R 1 . . H
  O4 0.47070(12) 0.20244(15) 0.22525(10) 0.0372(3) Uani d . 1 . . O
  Si1 0.61268(5) 0.23361(6) 0.17355(4) 0.03532(13) Uani d . 1 . . Si
  C10 0.5900(3) 0.1795(3) 0.03609(17) 0.0582(6) Uani d . 1 . . C
  H10A 0.5637 0.0742 0.0302 0.087 Uiso calc R 1 . . H
  H10B 0.6738 0.1941 0.0055 0.087 Uiso calc R 1 . . H
  H10C 0.5205 0.2419 0.0003 0.087 Uiso calc R 1 . . H
  C11 0.6533(2) 0.4356(3) 0.18729(18) 0.0501(5) Uani d . 1 . . C
  H11A 0.6170 0.4891 0.1258 0.075 Uiso calc R 1 . . H
  H11B 0.7502 0.4484 0.1965 0.075 Uiso calc R 1 . . H
  H11C 0.6141 0.4759 0.2469 0.075 Uiso calc R 1 . . H
  C12 0.7392(2) 0.1124(3) 0.24831(15) 0.0428(5) Uani d . 1 . . C
  C13 0.8753(2) 0.1316(3) 0.2051(2) 0.0647(7) Uani d . 1 . . C
  H13A 0.9416 0.0677 0.2433 0.097 Uiso calc R 1 . . H
  H13B 0.9035 0.2363 0.2117 0.097 Uiso calc R 1 . . H
  H13C 0.8672 0.1029 0.1328 0.097 Uiso calc R 1 . . H
  C14 0.7521(2) 0.1612(3) 0.36047(18) 0.0607(7) Uani d . 1 . . C
  H14A 0.6645 0.1573 0.3867 0.091 Uiso calc R 1 . . H
  H14B 0.7866 0.2636 0.3659 0.091 Uiso calc R 1 . . H
  H14C 0.8134 0.0938 0.4005 0.091 Uiso calc R 1 . . H
  C15 0.6982(2) -0.0524(3) 0.2397(2) 0.0601(7) Uani d . 1 . . C
  H15A 0.7666 -0.1142 0.2772 0.090 Uiso calc R 1 . . H
  H15B 0.6885 -0.0822 0.1677 0.090 Uiso calc R 1 . . H
  H15C 0.6132 -0.0663 0.2688 0.090 Uiso calc R 1 . . H
  S1 0.19777(5) 0.60295(6) 0.22149(4) 0.04069(13) Uani d . 1 . . S
  C16 0.23489(19) 0.7470(2) 0.31291(14) 0.0332(4) Uani d . 1 . . C
  C17 0.3673(2) 0.7821(2) 0.34352(17) 0.0416(5) Uani d . 1 . . C
  H17 0.4370 0.7293 0.3157 0.050 Uiso calc R 1 . . H
  C18 0.3967(2) 0.8932(2) 0.41392(17) 0.0447(5) Uani d . 1 . . C
  H18 0.4873 0.9159 0.4345 0.054 Uiso calc R 1 . . H
  C19 0.2976(2) 0.9733(2) 0.45583(15) 0.0416(5) Uani d . 1 . . C
  C20 0.1654(2) 0.9388(2) 0.42300(16) 0.0421(5) Uani d . 1 . . C
  H20 0.0959 0.9937 0.4496 0.051 Uiso calc R 1 . . H
  C21 0.1336(2) 0.8264(2) 0.35245(15) 0.0383(5) Uani d . 1 . . C
  H21 0.0432 0.8038 0.3313 0.046 Uiso calc R 1 . . H
  C22 0.3320(3) 1.0933(3) 0.53381(18) 0.0614(6) Uani d . 1 . . C
  H22A 0.4105 1.0629 0.5787 0.092 Uiso calc R 1 . . H
  H22B 0.2568 1.1086 0.5746 0.092 Uiso calc R 1 . . H
  H22C 0.3510 1.1867 0.4991 0.092 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1 0.0356(7) 0.0379(8) 0.0328(7) -0.0006(6) -0.0035(6) 0.0036(6)
  C1 0.0301(10) 0.0345(10) 0.0323(10) -0.0027(8) -0.0016(8) 0.0022(8)
  C2 0.0311(10) 0.0313(10) 0.0333(10) -0.0021(8) 0.0028(8) 0.0056(8)
  N1 0.0447(11) 0.0392(10) 0.0489(11) 0.0000(8) 0.0107(9) -0.0060(9)
  O2 0.0337(9) 0.0737(12) 0.0970(14) 0.0026(8) 0.0109(8) 0.0128(11)
  O3 0.0731(12) 0.0923(15) 0.0524(10) 0.0186(11) 0.0292(9) 0.0183(10)
  C3 0.0295(10) 0.0339(10) 0.0343(10) -0.0001(8) 0.0039(7) 0.0081(8)
  C4 0.0259(9) 0.0365(11) 0.0344(10) 0.0032(8) 0.0091(7) 0.0047(8)
  C5 0.0354(11) 0.0389(11) 0.0396(11) 0.0010(9) 0.0018(8) 0.0097(9)
  C6 0.0412(12) 0.0364(11) 0.0521(13) -0.0026(9) 0.0076(10) 0.0001(10)
  C7 0.0336(11) 0.0505(13) 0.0423(12) 0.0021(10) 0.0041(9) -0.0074(10)
  C8 0.0370(11) 0.0522(14) 0.0354(11) 0.0105(10) 0.0001(9) 0.0065(10)
  C9 0.0384(11) 0.0365(11) 0.0375(10) 0.0079(9) 0.0065(8) 0.0080(9)
  O4 0.0284(7) 0.0455(8) 0.0378(7) 0.0024(6) 0.0033(5) 0.0083(6)
  Si1 0.0318(3) 0.0439(3) 0.0310(3) -0.0024(2) 0.0065(2) -0.0034(2)
  C10 0.0607(15) 0.0773(17) 0.0371(12) -0.0078(13) 0.0082(10) -0.0090(11)
  C11 0.0434(12) 0.0530(14) 0.0551(13) -0.0070(11) 0.0116(10) -0.0008(11)
  C12 0.0339(11) 0.0537(12) 0.0420(11) 0.0055(10) 0.0094(8) -0.0015(11)
  C13 0.0355(13) 0.086(2) 0.0746(17) 0.0088(13) 0.0140(11) 0.0026(16)
  C14 0.0559(16) 0.0828(19) 0.0413(13) 0.0073(13) -0.0066(11) 0.0022(12)
  C15 0.0580(16) 0.0550(15) 0.0694(16) 0.0091(12) 0.0161(12) 0.0033(13)
  S1 0.0514(3) 0.0353(3) 0.0332(2) 0.0029(2) -0.0069(2) 0.0039(2)
  C16 0.0372(10) 0.0293(9) 0.0322(9) -0.0002(8) -0.0016(8) 0.0082(8)
  C17 0.0350(11) 0.0384(12) 0.0503(12) -0.0001(9) -0.0009(9) 0.0108(10)
  C18 0.0369(11) 0.0391(12) 0.0548(13) -0.0072(9) -0.0122(10) 0.0109(10)
  C19 0.0549(14) 0.0333(10) 0.0346(10) -0.0080(10) -0.0062(9) 0.0116(9)
  C20 0.0468(12) 0.0371(11) 0.0431(12) -0.0005(10) 0.0081(9) 0.0063(9)
  C21 0.0321(11) 0.0377(11) 0.0439(11) -0.0040(9) -0.0021(9) 0.0074(9)
  C22 0.0884(18) 0.0447(13) 0.0466(13) -0.0111(14) -0.0164(11) 0.0023(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C1 . 1.391(2) yes
  O1 C2 . 1.448(2) yes
  C1 C2 . 1.470(3) yes
  C1 N1 . 1.540(2) yes
  C1 S1 . 1.7656(19) yes
  C2 H2 . 1.000 ?
  C2 C3 . 1.515(3) yes
  N1 O2 . 1.212(2) yes
  N1 O3 . 1.207(2) yes
  C3 H3 . 1.000 ?
  C3 C4 . 1.502(3) ?
  C3 O4 . 1.419(2) ?
  C4 C5 . 1.392(3) ?
  C4 C9 . 1.383(3) ?
  C5 H5 . 0.950 ?
  C5 C6 . 1.380(3) ?
  C6 H6 . 0.950 ?
  C6 C7 . 1.373(3) ?
  C7 H7 . 0.950 ?
  C7 C8 . 1.380(3) ?
  C8 H8 . 0.950 ?
  C8 C9 . 1.387(3) ?
  C9 H9 . 0.950 ?
  O4 Si1 . 1.6673(13) ?
  Si1 C10 . 1.864(2) ?
  Si1 C11 . 1.858(2) ?
  Si1 C12 . 1.878(2) ?
  C10 H10A . 0.980 ?
  C10 H10B . 0.980 ?
  C10 H10C . 0.980 ?
  C11 H11A . 0.980 ?
  C11 H11B . 0.980 ?
  C11 H11C . 0.980 ?
  C12 C13 . 1.546(3) ?
  C12 C14 . 1.531(3) ?
  C12 C15 . 1.532(3) ?
  C13 H13A . 0.980 ?
  C13 H13B . 0.980 ?
  C13 H13C . 0.980 ?
  C14 H14A . 0.980 ?
  C14 H14B . 0.980 ?
  C14 H14C . 0.980 ?
  C15 H15A . 0.980 ?
  C15 H15B . 0.980 ?
  C15 H15C . 0.980 ?
  S1 C16 . 1.777(2) yes
  C16 C17 . 1.394(3) ?
  C16 C21 . 1.386(3) ?
  C17 H17 . 0.950 ?
  C17 C18 . 1.370(3) ?
  C18 H18 . 0.950 ?
  C18 C19 . 1.386(3) ?
  C19 C20 . 1.397(3) ?
  C19 C22 . 1.502(3) ?
  C20 H20 . 0.950 ?
  C20 C21 . 1.385(3) ?
  C21 H21 . 0.950 ?
  C22 H22A . 0.980 ?
  C22 H22B . 0.980 ?
  C22 H22C . 0.980 ?