##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-[(1S,2S,3R)-2-Bromo-3-(tert-butyldiphenylsilyloxy)-1-phenyl-4-
(phenylsulfonyl)butyl]-4-methylbenzenesulfonamide
;
_chemical_formula_moiety     'C39 H42 Br N O5 S2 Si'
_chemical_formula_sum     'C39 H42 Br N O5 S2 Si'
_chemical_formula_iupac     'C39 H42 Br N O5 S2 Si'
_chemical_formula_weight     776.86
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     13.9704(8)
_cell_length_b     19.5590(12)
_cell_length_c     14.1646(9)
_cell_angle_alpha     90.00
_cell_angle_beta     96.9000(10)
_cell_angle_gamma     90.00
_cell_volume     3842.4(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4427
_cell_measurement_theta_min     2.42
_cell_measurement_theta_max     22.75
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Needle
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.345
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1616
_exptl_absorpt_coefficient_mu     1.252
_exptl_absorpt_correction_type     none
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Smart APEX CCD area-detector'
_diffrn_measurement_device     'Bruker SMART APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     23909
_diffrn_reflns_av_R_equivalents     0.0398
_diffrn_reflns_av_sigmaI/netI     0.0576
_diffrn_reflns_theta_min     1.78
_diffrn_reflns_theta_max     28.01
_diffrn_reflns_theta_full     28.01
_diffrn_measured_fraction_theta_max     0.927
_diffrn_measured_fraction_theta_full     0.927
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     8859
_reflns_number_gt     5593
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0931
_refine_ls_R_factor_gt     0.0514
_refine_ls_wR_factor_gt     0.1141
_refine_ls_wR_factor_ref     0.1303
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     8859
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.072P)²+0.603P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.003
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     0.624
_refine_diff_density_min     -0.561
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Si' 'Si' 0.0817 0.0704
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material     'SHELXL97 and PARST (Nardelli, 1995)'
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
    Br1 0.58188(2) 0.208667(16) 0.66847(3) 0.06261(14) Uani d . 1 . . Br
    C1 0.58772(18) 0.34824(13) 0.6178(2) 0.0370(6) Uani d . 1 . . C
    H1 0.6103 0.3504 0.6860 0.044 Uiso calc R 1 . . H
    C2 0.51861(18) 0.28690(13) 0.6006(2) 0.0373(6) Uani d . 1 . . C
    H2 0.5132 0.2763 0.5326 0.045 Uiso calc R 1 . . H
    C3 0.41601(18) 0.29696(13) 0.62589(18) 0.0354(6) Uani d . 1 . . C
    H3 0.3847 0.3326 0.5845 0.043 Uiso calc R 1 . . H
    C4 0.41414(18) 0.31874(14) 0.72899(18) 0.0380(6) Uani d . 1 . . C
    H4A 0.4644 0.3523 0.7456 0.046 Uiso calc R 1 . . H
    H4B 0.4280 0.2794 0.7700 0.046 Uiso calc R 1 . . H
    C5 0.3265(2) 0.38390(16) 0.8678(2) 0.0443(7) Uani d . 1 . . C
    C6 0.3651(2) 0.44778(17) 0.8859(3) 0.0581(8) Uani d . 1 . . C
    H6 0.3771 0.4764 0.8362 0.070 Uiso calc R 1 . . H
    C7 0.3859(2) 0.4687(2) 0.9790(3) 0.0700(10) Uani d . 1 . . C
    H7 0.4118 0.5120 0.9924 0.084 Uiso calc R 1 . . H
    C8 0.3690(3) 0.4268(2) 1.0510(3) 0.0796(12) Uani d . 1 . . C
    H8 0.3845 0.4412 1.1135 0.095 Uiso calc R 1 . . H
    C9 0.3290(3) 0.3633(2) 1.0329(3) 0.0776(11) Uani d . 1 . . C
    H9 0.3164 0.3351 1.0827 0.093 Uiso calc R 1 . . H
    C10 0.3080(3) 0.34193(17) 0.9405(2) 0.0592(9) Uani d . 1 . . C
    H10 0.2811 0.2989 0.9274 0.071 Uiso calc R 1 . . H
    C11 0.67958(19) 0.50421(14) 0.63723(19) 0.0398(6) Uani d . 1 . . C
    C12 0.7490(2) 0.50595(16) 0.7156(2) 0.0520(8) Uani d . 1 . . C
    H12 0.7332 0.4945 0.7756 0.062 Uiso calc R 1 . . H
    C13 0.8410(2) 0.52472(19) 0.7036(2) 0.0643(9) Uani d . 1 . . C
    H13 0.8875 0.5263 0.7564 0.077 Uiso calc R 1 . . H
    C14 0.8669(2) 0.54136(18) 0.6153(2) 0.0585(9) Uani d . 1 . . C
    C15 0.7969(2) 0.53846(16) 0.5380(2) 0.0557(8) Uani d . 1 . . C
    H15 0.8130 0.5491 0.4779 0.067 Uiso calc R 1 . . H
    C16 0.7035(2) 0.52010(15) 0.5481(2) 0.0488(7) Uani d . 1 . . C
    H16 0.6570 0.5184 0.4954 0.059 Uiso calc R 1 . . H
    C17 0.9684(2) 0.5628(2) 0.6035(3) 0.0906(13) Uani d . 1 . . C
    H17A 1.0103 0.5238 0.6119 0.136 Uiso calc R 1 . . H
    H17B 0.9897 0.5968 0.6501 0.136 Uiso calc R 1 . . H
    H17C 0.9700 0.5813 0.5409 0.136 Uiso calc R 1 . . H
    C18 0.67524(19) 0.34150(14) 0.5646(2) 0.0446(7) Uani d . 1 . . C
    C19 0.6638(2) 0.34411(15) 0.4664(2) 0.0566(8) Uani d . 1 . . C
    H19 0.6023 0.3473 0.4333 0.068 Uiso calc R 1 . . H
    C20 0.7440(3) 0.34199(18) 0.4167(3) 0.0759(11) Uani d . 1 . . C
    H20 0.7364 0.3436 0.3506 0.091 Uiso calc R 1 . . H
    C21 0.8340(3) 0.3376(2) 0.4662(4) 0.0909(15) Uani d . 1 . . C
    H21 0.8877 0.3368 0.4333 0.109 Uiso calc R 1 . . H
    C22 0.8465(3) 0.3343(2) 0.5627(4) 0.0841(13) Uani d . 1 . . C
    H22 0.9083 0.3308 0.5952 0.101 Uiso calc R 1 . . H
    C23 0.7665(2) 0.33618(16) 0.6127(3) 0.0629(9) Uani d . 1 . . C
    H23 0.7749 0.3339 0.6787 0.075 Uiso calc R 1 . . H
    C24 0.3718(2) 0.22678(15) 0.41022(19) 0.0408(7) Uani d . 1 . . C
    C25 0.4497(2) 0.19458(19) 0.3782(2) 0.0611(9) Uani d . 1 . . C
    H25 0.4710 0.1532 0.4053 0.073 Uiso calc R 1 . . H
    C26 0.4964(3) 0.2222(2) 0.3073(3) 0.0801(12) Uani d . 1 . . C
    H26 0.5494 0.1997 0.2878 0.096 Uiso calc R 1 . . H
    C27 0.4656(3) 0.2824(2) 0.2651(3) 0.0828(13) Uani d . 1 . . C
    H27 0.4964 0.3006 0.2161 0.099 Uiso calc R 1 . . H
    C28 0.3897(3) 0.3152(2) 0.2954(3) 0.0777(11) Uani d . 1 . . C
    H28 0.3686 0.3564 0.2675 0.093 Uiso calc R 1 . . H
    C29 0.3439(3) 0.28806(17) 0.3669(2) 0.0606(9) Uani d . 1 . . C
    H29 0.2922 0.3117 0.3870 0.073 Uiso calc R 1 . . H
    C30 0.35169(19) 0.10265(15) 0.5414(2) 0.0444(7) Uani d . 1 . . C
    C31 0.3542(2) 0.05377(17) 0.4708(3) 0.0609(9) Uani d . 1 . . C
    H31 0.3445 0.0674 0.4075 0.073 Uiso calc R 1 . . H
    C32 0.3707(3) -0.0145(2) 0.4914(4) 0.0827(13) Uani d . 1 . . C
    H32 0.3719 -0.0460 0.4424 0.099 Uiso calc R 1 . . H
    C33 0.3850(3) -0.0355(2) 0.5830(5) 0.0902(15) Uani d . 1 . . C
    H33 0.3955 -0.0816 0.5968 0.108 Uiso calc R 1 . . H
    C34 0.3843(3) 0.0104(2) 0.6547(3) 0.0851(13) Uani d . 1 . . C
    H34 0.3943 -0.0042 0.7176 0.102 Uiso calc R 1 . . H
    C35 0.3684(2) 0.07973(18) 0.6344(3) 0.0642(9) Uani d . 1 . . C
    H35 0.3690 0.1109 0.6840 0.077 Uiso calc R 1 . . H
    C36 0.1812(2) 0.19846(15) 0.5030(2) 0.0453(7) Uani d . 1 . . C
    C37 0.1394(2) 0.15857(19) 0.4145(2) 0.0651(10) Uani d . 1 . . C
    H37A 0.0703 0.1595 0.4094 0.098 Uiso calc R 1 . . H
    H37B 0.1615 0.1121 0.4197 0.098 Uiso calc R 1 . . H
    H37C 0.1604 0.1792 0.3590 0.098 Uiso calc R 1 . . H
    C38 0.1465(2) 0.1650(2) 0.5910(2) 0.0657(10) Uani d . 1 . . C
    H38A 0.1711 0.1902 0.6469 0.099 Uiso calc R 1 . . H
    H38B 0.1694 0.1187 0.5965 0.099 Uiso calc R 1 . . H
    H38C 0.0773 0.1652 0.5846 0.099 Uiso calc R 1 . . H
    C39 0.1426(2) 0.27209(19) 0.4962(3) 0.0783(11) Uani d . 1 . . C
    H39A 0.1554 0.2919 0.4370 0.117 Uiso calc R 1 . . H
    H39B 0.1740 0.2986 0.5480 0.117 Uiso calc R 1 . . H
    H39C 0.0744 0.2717 0.4993 0.117 Uiso calc R 1 . . H
    N1 0.53386(14) 0.41190(10) 0.59082(15) 0.0362(5) Uani d . 1 . . N
    H1A 0.4889 0.4120 0.5436 0.043 Uiso calc R 1 . . H
    O1 0.2834(2) 0.41091(16) 0.68720(17) 0.0974(10) Uani d . 1 . . O
    O2 0.23100(18) 0.30129(17) 0.74917(19) 0.1004(11) Uani d . 1 . . O
    O3 0.36095(13) 0.23622(10) 0.61151(12) 0.0433(5) Uani d . 1 . . O
    O4 0.55618(14) 0.46619(10) 0.74889(13) 0.0482(5) Uani d . 1 . . O
    O5 0.49736(13) 0.53253(9) 0.60528(13) 0.0463(5) Uani d . 1 . . O
    S1 0.30168(6) 0.35403(5) 0.74997(6) 0.0571(2) Uani d . 1 . . S
    S2 0.56020(5) 0.48139(3) 0.65088(5) 0.03767(17) Uani d . 1 . . S
    Si1 0.31707(5) 0.19352(4) 0.51599(5) 0.03609(18) Uani d . 1 . . Si
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Br1 C2 . 1.960(3) y
    C1 N1 . 1.481(3) ?
    C1 C18 . 1.517(4) ?
    C1 C2 . 1.541(3) ?
    C1 H1 . 0.9800 ?
    C2 C3 . 1.531(4) ?
    C2 H2 . 0.9800 ?
    C3 O3 . 1.417(3) ?
    C3 C4 . 1.525(4) ?
    C3 H3 . 0.9800 ?
    C4 S1 . 1.773(3) y
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C10 . 1.366(4) ?
    C5 C6 . 1.373(4) ?
    C5 S1 . 1.764(3) y
    C6 C7 . 1.378(5) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.350(5) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.373(5) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.371(5) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11 C16 . 1.380(4) ?
    C11 C12 . 1.384(4) ?
    C11 S2 . 1.759(3) y
    C12 C13 . 1.367(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.382(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.380(4) ?
    C14 C17 . 1.507(4) ?
    C15 C16 . 1.377(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 C23 . 1.376(4) ?
    C18 C19 . 1.382(4) ?
    C19 C20 . 1.394(4) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.367(6) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.357(6) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.394(5) ?
    C22 H22 . 0.9300 ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.380(4) ?
    C24 C29 . 1.381(4) ?
    C24 Si1 . 1.878(3) y
    C25 C26 . 1.373(5) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.368(6) ?
    C26 H26 . 0.9300 ?
    C27 C28 . 1.352(6) ?
    C27 H27 . 0.9300 ?
    C28 C29 . 1.369(5) ?
    C28 H28 . 0.9300 ?
    C29 H29 . 0.9300 ?
    C30 C35 . 1.384(4) ?
    C30 C31 . 1.387(4) ?
    C30 Si1 . 1.866(3) y
    C31 C32 . 1.380(5) ?
    C31 H31 . 0.9300 ?
    C32 C33 . 1.352(6) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.358(6) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.398(5) ?
    C34 H34 . 0.9300 ?
    C35 H35 . 0.9300 ?
    C36 C37 . 1.531(4) ?
    C36 C39 . 1.537(4) ?
    C36 C38 . 1.537(4) ?
    C36 Si1 . 1.887(3) y
    C37 H37A . 0.9600 ?
    C37 H37B . 0.9600 ?
    C37 H37C . 0.9600 ?
    C38 H38A . 0.9600 ?
    C38 H38B . 0.9600 ?
    C38 H38C . 0.9600 ?
    C39 H39A . 0.9600 ?
    C39 H39B . 0.9600 ?
    C39 H39C . 0.9600 ?
    N1 S2 . 1.622(2) y
    N1 H1A . 0.8600 ?
    O1 S1 . 1.428(3) y
    O2 S1 . 1.427(3) y
    O3 Si1 . 1.6446(19) y
    O4 S2 . 1.4275(19) y
    O5 S2 . 1.4325(19) y
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C1 C18 . . 111.1(2) ?
    N1 C1 C2 . . 108.9(2) ?
    C18 C1 C2 . . 112.4(2) ?
    N1 C1 H1 . . 108.1 ?
    C18 C1 H1 . . 108.1 ?
    C2 C1 H1 . . 108.1 ?
    C3 C2 C1 . . 116.7(2) ?
    C3 C2 Br1 . . 111.43(17) ?
    C1 C2 Br1 . . 107.06(17) ?
    C3 C2 H2 . . 107.1 ?
    C1 C2 H2 . . 107.1 ?
    Br1 C2 H2 . . 107.1 ?
    O3 C3 C4 . . 107.5(2) ?
    O3 C3 C2 . . 111.5(2) ?
    C4 C3 C2 . . 112.6(2) ?
    O3 C3 H3 . . 108.4 ?
    C4 C3 H3 . . 108.4 ?
    C2 C3 H3 . . 108.4 ?
    C3 C4 S1 . . 112.75(18) ?
    C3 C4 H4A . . 109.0 ?
    S1 C4 H4A . . 109.0 ?
    C3 C4 H4B . . 109.0 ?
    S1 C4 H4B . . 109.0 ?
    H4A C4 H4B . . 107.8 ?
    C10 C5 C6 . . 120.8(3) ?
    C10 C5 S1 . . 118.8(2) ?
    C6 C5 S1 . . 120.4(3) ?
    C5 C6 C7 . . 118.8(3) ?
    C5 C6 H6 . . 120.6 ?
    C7 C6 H6 . . 120.6 ?
    C8 C7 C6 . . 120.4(4) ?
    C8 C7 H7 . . 119.8 ?
    C6 C7 H7 . . 119.8 ?
    C7 C8 C9 . . 120.8(4) ?
    C7 C8 H8 . . 119.6 ?
    C9 C8 H8 . . 119.6 ?
    C8 C9 C10 . . 119.4(4) ?
    C8 C9 H9 . . 120.3 ?
    C10 C9 H9 . . 120.3 ?
    C5 C10 C9 . . 119.8(3) ?
    C5 C10 H10 . . 120.1 ?
    C9 C10 H10 . . 120.1 ?
    C16 C11 C12 . . 120.4(3) ?
    C16 C11 S2 . . 119.6(2) ?
    C12 C11 S2 . . 120.0(2) ?
    C13 C12 C11 . . 119.0(3) ?
    C13 C12 H12 . . 120.5 ?
    C11 C12 H12 . . 120.5 ?
    C12 C13 C14 . . 121.9(3) ?
    C12 C13 H13 . . 119.0 ?
    C14 C13 H13 . . 119.0 ?
    C15 C14 C13 . . 118.1(3) ?
    C15 C14 C17 . . 120.7(3) ?
    C13 C14 C17 . . 121.2(3) ?
    C16 C15 C14 . . 121.2(3) ?
    C16 C15 H15 . . 119.4 ?
    C14 C15 H15 . . 119.4 ?
    C15 C16 C11 . . 119.4(3) ?
    C15 C16 H16 . . 120.3 ?
    C11 C16 H16 . . 120.3 ?
    C14 C17 H17A . . 109.5 ?
    C14 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C14 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C23 C18 C19 . . 119.3(3) ?
    C23 C18 C1 . . 121.0(3) ?
    C19 C18 C1 . . 119.6(3) ?
    C18 C19 C20 . . 120.3(3) ?
    C18 C19 H19 . . 119.9 ?
    C20 C19 H19 . . 119.9 ?
    C21 C20 C19 . . 119.2(4) ?
    C21 C20 H20 . . 120.4 ?
    C19 C20 H20 . . 120.4 ?
    C22 C21 C20 . . 121.3(4) ?
    C22 C21 H21 . . 119.3 ?
    C20 C21 H21 . . 119.3 ?
    C21 C22 C23 . . 119.7(4) ?
    C21 C22 H22 . . 120.2 ?
    C23 C22 H22 . . 120.2 ?
    C18 C23 C22 . . 120.2(4) ?
    C18 C23 H23 . . 119.9 ?
    C22 C23 H23 . . 119.9 ?
    C25 C24 C29 . . 116.2(3) ?
    C25 C24 Si1 . . 121.1(2) ?
    C29 C24 Si1 . . 122.3(2) ?
    C26 C25 C24 . . 121.6(3) ?
    C26 C25 H25 . . 119.2 ?
    C24 C25 H25 . . 119.2 ?
    C27 C26 C25 . . 120.4(4) ?
    C27 C26 H26 . . 119.8 ?
    C25 C26 H26 . . 119.8 ?
    C28 C27 C26 . . 119.2(3) ?
    C28 C27 H27 . . 120.4 ?
    C26 C27 H27 . . 120.4 ?
    C27 C28 C29 . . 120.3(4) ?
    C27 C28 H28 . . 119.8 ?
    C29 C28 H28 . . 119.8 ?
    C28 C29 C24 . . 122.2(3) ?
    C28 C29 H29 . . 118.9 ?
    C24 C29 H29 . . 118.9 ?
    C35 C30 C31 . . 116.5(3) ?
    C35 C30 Si1 . . 120.1(2) ?
    C31 C30 Si1 . . 123.1(2) ?
    C32 C31 C30 . . 122.2(4) ?
    C32 C31 H31 . . 118.9 ?
    C30 C31 H31 . . 118.9 ?
    C33 C32 C31 . . 119.9(4) ?
    C33 C32 H32 . . 120.0 ?
    C31 C32 H32 . . 120.0 ?
    C32 C33 C34 . . 120.2(4) ?
    C32 C33 H33 . . 119.9 ?
    C34 C33 H33 . . 119.9 ?
    C33 C34 C35 . . 120.2(4) ?
    C33 C34 H34 . . 119.9 ?
    C35 C34 H34 . . 119.9 ?
    C30 C35 C34 . . 121.0(4) ?
    C30 C35 H35 . . 119.5 ?
    C34 C35 H35 . . 119.5 ?
    C37 C36 C39 . . 109.2(3) ?
    C37 C36 C38 . . 108.7(3) ?
    C39 C36 C38 . . 107.9(3) ?
    C37 C36 Si1 . . 109.5(2) ?
    C39 C36 Si1 . . 113.3(2) ?
    C38 C36 Si1 . . 108.1(2) ?
    C36 C37 H37A . . 109.5 ?
    C36 C37 H37B . . 109.5 ?
    H37A C37 H37B . . 109.5 ?
    C36 C37 H37C . . 109.5 ?
    H37A C37 H37C . . 109.5 ?
    H37B C37 H37C . . 109.5 ?
    C36 C38 H38A . . 109.5 ?
    C36 C38 H38B . . 109.5 ?
    H38A C38 H38B . . 109.5 ?
    C36 C38 H38C . . 109.5 ?
    H38A C38 H38C . . 109.5 ?
    H38B C38 H38C . . 109.5 ?
    C36 C39 H39A . . 109.5 ?
    C36 C39 H39B . . 109.5 ?
    H39A C39 H39B . . 109.5 ?
    C36 C39 H39C . . 109.5 ?
    H39A C39 H39C . . 109.5 ?
    H39B C39 H39C . . 109.5 ?
    C1 N1 S2 . . 119.54(17) ?
    C1 N1 H1A . . 120.2 ?
    S2 N1 H1A . . 120.2 ?
    C3 O3 Si1 . . 133.35(16) ?
    O2 S1 O1 . . 119.1(2) ?
    O2 S1 C5 . . 107.71(15) ?
    O1 S1 C5 . . 109.37(16) ?
    O2 S1 C4 . . 110.08(16) ?
    O1 S1 C4 . . 107.12(15) y
    C5 S1 C4 . . 102.12(13) y
    O4 S2 O5 . . 119.36(12) ?
    O4 S2 N1 . . 107.62(11) y
    O5 S2 N1 . . 105.10(11) ?
    O4 S2 C11 . . 107.95(12) y
    O5 S2 C11 . . 108.12(12) ?
    N1 S2 C11 . . 108.25(12) y
    O3 Si1 C30 . . 105.24(12) y
    O3 Si1 C24 . . 109.46(11) y
    C30 Si1 C24 . . 111.28(13) y
    O3 Si1 C36 . . 108.98(11) ?
    C30 Si1 C36 . . 107.58(12) ?
    C24 Si1 C36 . . 113.92(13) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C1 C2 C3 . . . . -39.2(3) ?
    C18 C1 C2 C3 . . . . -162.8(2) ?
    N1 C1 C2 Br1 . . . . -164.84(17) ?
    C18 C1 C2 Br1 . . . . 71.6(2) ?
    C1 C2 C3 O3 . . . . -177.1(2) ?
    Br1 C2 C3 O3 . . . . -53.7(2) ?
    C1 C2 C3 C4 . . . . -56.2(3) ?
    Br1 C2 C3 C4 . . . . 67.2(2) ?
    O3 C3 C4 S1 . . . . -74.0(2) ?
    C2 C3 C4 S1 . . . . 162.85(18) ?
    C10 C5 C6 C7 . . . . 0.7(5) ?
    S1 C5 C6 C7 . . . . -178.3(2) ?
    C5 C6 C7 C8 . . . . 0.3(5) ?
    C6 C7 C8 C9 . . . . -1.3(6) ?
    C7 C8 C9 C10 . . . . 1.3(6) ?
    C6 C5 C10 C9 . . . . -0.7(5) ?
    S1 C5 C10 C9 . . . . 178.3(3) ?
    C8 C9 C10 C5 . . . . -0.2(5) ?
    C16 C11 C12 C13 . . . . 1.1(5) ?
    S2 C11 C12 C13 . . . . -179.1(3) ?
    C11 C12 C13 C14 . . . . -0.6(5) ?
    C12 C13 C14 C15 . . . . -0.2(5) ?
    C12 C13 C14 C17 . . . . 179.3(4) ?
    C13 C14 C15 C16 . . . . 0.5(5) ?
    C17 C14 C15 C16 . . . . -178.9(3) ?
    C14 C15 C16 C11 . . . . -0.1(5) ?
    C12 C11 C16 C15 . . . . -0.7(4) ?
    S2 C11 C16 C15 . . . . 179.5(2) ?
    N1 C1 C18 C23 . . . . 121.5(3) ?
    C2 C1 C18 C23 . . . . -116.1(3) ?
    N1 C1 C18 C19 . . . . -55.3(3) ?
    C2 C1 C18 C19 . . . . 67.1(3) ?
    C23 C18 C19 C20 . . . . -0.6(4) ?
    C1 C18 C19 C20 . . . . 176.3(3) ?
    C18 C19 C20 C21 . . . . -0.2(5) ?
    C19 C20 C21 C22 . . . . 0.9(6) ?
    C20 C21 C22 C23 . . . . -0.7(6) ?
    C19 C18 C23 C22 . . . . 0.8(5) ?
    C1 C18 C23 C22 . . . . -176.0(3) ?
    C21 C22 C23 C18 . . . . -0.1(6) ?
    C29 C24 C25 C26 . . . . 0.0(5) ?
    Si1 C24 C25 C26 . . . . -173.3(3) ?
    C24 C25 C26 C27 . . . . -1.1(6) ?
    C25 C26 C27 C28 . . . . 1.4(6) ?
    C26 C27 C28 C29 . . . . -0.6(6) ?
    C27 C28 C29 C24 . . . . -0.5(6) ?
    C25 C24 C29 C28 . . . . 0.8(5) ?
    Si1 C24 C29 C28 . . . . 174.0(3) ?
    C35 C30 C31 C32 . . . . 1.2(5) ?
    Si1 C30 C31 C32 . . . . -173.4(2) ?
    C30 C31 C32 C33 . . . . 0.0(5) ?
    C31 C32 C33 C34 . . . . -0.7(6) ?
    C32 C33 C34 C35 . . . . 0.2(6) ?
    C31 C30 C35 C34 . . . . -1.6(5) ?
    Si1 C30 C35 C34 . . . . 173.1(3) ?
    C33 C34 C35 C30 . . . . 1.0(6) ?
    C18 C1 N1 S2 . . . . -90.7(2) ?
    C2 C1 N1 S2 . . . . 144.92(18) ?
    C4 C3 O3 Si1 . . . . 167.12(19) ?
    C2 C3 O3 Si1 . . . . -69.1(3) ?
    C10 C5 S1 O2 . . . . 23.0(3) ?
    C6 C5 S1 O2 . . . . -157.9(3) ?
    C10 C5 S1 O1 . . . . 153.9(3) ?
    C6 C5 S1 O1 . . . . -27.1(3) ?
    C10 C5 S1 C4 . . . . -92.9(3) ?
    C6 C5 S1 C4 . . . . 86.1(3) ?
    C3 C4 S1 O2 . . . . 73.2(2) ?
    C3 C4 S1 O1 . . . . -57.7(2) ?
    C3 C4 S1 C5 . . . . -172.6(2) ?
    C1 N1 S2 O4 . . . . -53.2(2) ?
    C1 N1 S2 O5 . . . . 178.62(18) ?
    C1 N1 S2 C11 . . . . 63.3(2) ?
    C16 C11 S2 O4 . . . . 178.7(2) ?
    C12 C11 S2 O4 . . . . -1.1(3) ?
    C16 C11 S2 O5 . . . . -50.9(3) ?
    C12 C11 S2 O5 . . . . 129.3(2) ?
    C16 C11 S2 N1 . . . . 62.5(3) ?
    C12 C11 S2 N1 . . . . -117.3(2) ?
    C3 O3 Si1 C30 . . . . 131.7(2) ?
    C3 O3 Si1 C24 . . . . 12.1(3) ?
    C3 O3 Si1 C36 . . . . -113.1(2) ?
    C35 C30 Si1 O3 . . . . 25.4(3) ?
    C31 C30 Si1 O3 . . . . -160.2(2) ?
    C35 C30 Si1 C24 . . . . 143.9(2) ?
    C31 C30 Si1 C24 . . . . -41.7(3) ?
    C35 C30 Si1 C36 . . . . -90.7(2) ?
    C31 C30 Si1 C36 . . . . 83.7(3) ?
    C25 C24 Si1 O3 . . . . 97.1(3) ?
    C29 C24 Si1 O3 . . . . -75.8(3) ?
    C25 C24 Si1 C30 . . . . -18.8(3) ?
    C29 C24 Si1 C30 . . . . 168.3(3) ?
    C25 C24 Si1 C36 . . . . -140.6(2) ?
    C29 C24 Si1 C36 . . . . 46.5(3) ?
    C37 C36 Si1 O3 . . . . -179.7(2) ?
    C39 C36 Si1 O3 . . . . 58.1(3) ?
    C38 C36 Si1 O3 . . . . -61.5(2) ?
    C37 C36 Si1 C30 . . . . -66.1(2) ?
    C39 C36 Si1 C30 . . . . 171.7(2) ?
    C38 C36 Si1 C30 . . . . 52.1(2) ?
    C37 C36 Si1 C24 . . . . 57.7(3) ?
    C39 C36 Si1 C24 . . . . -64.5(3) ?
    C38 C36 Si1 C24 . . . . 176.0(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C1 H1 O4 . 0.98 2.58 3.027(5) 108
    C4 H4A O4 . 0.97 2.57 3.493(3) 160
    C10 H10 O2 . 0.93 2.54 2.904(2) 104
    C12 H12 O4 . 0.93 2.52 2.896(2) 105
    N1 H1A O5 3_666 0.86 2.40 2.966(3) 124
data_global
_journal_date_recd_electronic     2004-11-01
_journal_date_accepted     2004-11-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     12
_journal_page_first     o2290
_journal_page_last     o2292
_journal_paper_category     EO
_publ_contact_author_name     'Dr. G.Y.S.K. Swamy'
_publ_contact_author_address
;  Laboratory of X-ray Crystallography
   Indian Institute of Chemical Technolgoy
   Hyderabad - 500 007
;
_publ_contact_author_email     swamy@ins.iictnet.com
_publ_contact_author_fax     '091 040 2719 3118'
_publ_contact_author_phone     '091 040 2719 3118'
_publ_section_title
;
N-[(1S,2S,3R)-2-Bromo-3-(tert-butyldiphenylsilyloxy)-1-phenyl-4-
(phenylsulfonyl)butyl]-4-methylbenzenesulfonamide
;
loop_
    _publ_author_name
    _publ_author_address
    'K. Ravikumar'
;
Laboratory of X-ray Crystallography
Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'G. Y. S. K. Swamy'
;
Laboratory of X-ray Crystallography
Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'S. Raghavan'
;
Organic Division I
Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'Ch. Naveenkumar'
;
Organic Division I
Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
