# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 182/1358
 
#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 1999-05-05 at 17:17:34
#  Using CIFtbx version 2.6.2 16 Jun 1998
 
#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.1beta3
#  Request file    : c:\wingx\files\archive.dat
#  CIF files read  : s92
 
 
data_s92
 
_audit_creation_date            1999-05-05T17:17:34-00:00
_audit_creation_method         'WinGX routine CIF_UPDATE'
_audit_conform_dict_name        cif_core.dic
_audit_conform_dict_version     2.1beta3
_audit_conform_dict_location    ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic
_publ_requested_category        FO
 
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_sum                   'C23 H38 N2 O4 S2'
_chemical_formula_weight                470.67
 
#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
 
_symmetry_cell_setting                  Triclinic
_symmetry_space_group_name_H-M          P-1
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
 
_cell_length_a                          9.891(2)
_cell_length_b                          10.419(2)
_cell_length_c                          13.574(3)
_cell_angle_alpha                       67.91(3)
_cell_angle_beta                        74.89(3)
_cell_angle_gamma                       87.88(3)
_cell_volume                            1248.4(4)
_cell_formula_units_Z                   2
_cell_measurement_temperature           293(2)
 
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
 
_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.15
_exptl_crystal_size_mid                 0.15
_exptl_crystal_size_min                 0.05
_exptl_crystal_density_diffrn           1.252
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    508
_exptl_special_details
;
 ?
;
 
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
 
_exptl_absorpt_coefficient_mu           0.244
_exptl_absorpt_correction_type          multi-scans
_exptl_absorpt_correction_T_min         0.912
_exptl_absorpt_correction_T_max         0.995
 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
 
_diffrn_ambient_temperature             293(2)
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_measurement_device_type         'Nonius KappaCCD area detector'
_diffrn_measurement_method              'Phi + omega scans'
_diffrn_reflns_number                   19877
_diffrn_reflns_av_R_equivalents         0.0968
_diffrn_reflns_av_sigmaI/netI           0.0686
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -11
_diffrn_reflns_limit_k_max              11
_diffrn_reflns_limit_l_min              -14
_diffrn_reflns_limit_l_max              14
_diffrn_reflns_theta_min                1.68
_diffrn_reflns_theta_max                22.5
_diffrn_reflns_theta_full               22.5
_diffrn_measured_fraction_theta_full
                                        1
_diffrn_measured_fraction_theta_max
                                        1
_reflns_number_total                    3267
_reflns_number_gt                       2147
_reflns_threshold_expression            >2sigma(I)
 
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
 
_computing_data_collection
;
        DENZO (Otwinowski and Minor, 1997)
        COLLECT (Hooft, 1989)
;
_computing_cell_refinement              'DENZO and COLLECT'
_computing_data_reduction               'DENZO and COLLECT'
_computing_structure_solution           'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'CAMERON (Watkin and Pearce, 1996)'
 
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
 
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_weighting_scheme
         'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_atom_sites_solution_hydrogens          geom
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            none
_refine_ls_number_reflns                3267
_refine_ls_number_parameters            285
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0931
_refine_ls_R_factor_gt                  0.0556
_refine_ls_wR_factor_ref                0.1593
_refine_ls_wR_factor_gt                 0.1348
_refine_ls_goodness_of_fit_ref          0.964
_refine_ls_restrained_S_all             0.964
_refine_ls_shift/su_max                 0
_refine_ls_shift/su_mean                0
_refine_diff_density_max                0.342
_refine_diff_density_min                -0.308
_refine_diff_density_rms                0.068
 
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
 
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 0 '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'
O O 0.0106 0.006 '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'
 
loop_
    _atom_site_label
    _atom_site_type_symbol
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_occupancy
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_assembly
    _atom_site_disorder_group
S1 S 0.80196(10) 0.76591(10) 0.40864(8) 0.0683(4) Uani 1 d . . .
S2 S 0.99644(11) 1.02448(10) 0.31943(9) 0.0712(4) Uani 1 d . . .
N1 N 1.1948(3) 0.7107(3) 0.0184(2) 0.0631(8) Uani 1 d . . .
N2 N 1.0856(3) 0.6849(3) 0.3853(2) 0.0636(8) Uani 1 d . . .
O1 O 1.3873(3) 0.7399(3) 0.2783(3) 0.0987(10) Uani 1 d . . .
O2 O 1.4062(3) 0.5132(3) 0.3510(2) 0.0882(9) Uani 1 d . . .
O3 O 1.3228(3) 0.6712(3) -0.1299(2) 0.0855(9) Uani 1 d . . .
O4 O 1.4250(3) 0.7611(3) -0.0371(2) 0.0784(8) Uani 1 d . . .
C1 C 0.6716(4) 0.8894(5) 0.4167(4) 0.0895(14) Uani 1 d . . .
H1A H 0.645 0.9252 0.3479 0.107 Uiso 1 calc R . .
H1B H 0.5888 0.8413 0.4749 0.107 Uiso 1 calc R . .
C2 C 0.7175(5) 1.0104(5) 0.4387(4) 0.0992(15) Uani 1 d . . .
H2A H 0.6372 1.0638 0.4521 0.119 Uiso 1 calc R . .
H2B H 0.7499 0.975 0.505 0.119 Uiso 1 calc R . .
C3 C 0.8327(4) 1.1051(4) 0.3453(4) 0.0842(13) Uani 1 d . . .
H3A H 0.8496 1.1851 0.3616 0.101 Uiso 1 calc R . .
H3B H 0.8009 1.1382 0.2787 0.101 Uiso 1 calc R . .
C4 C 0.9422(3) 0.8759(3) 0.2932(3) 0.0561(9) Uani 1 d . . .
C5 C 0.9026(4) 0.9307(4) 0.1844(3) 0.0594(10) Uani 1 d . . .
H5A H 0.8253 0.9899 0.1901 0.071 Uiso 1 calc R . .
H5B H 0.9818 0.9876 0.1269 0.071 Uiso 1 calc R . .
C6 C 0.8604(4) 0.8185(4) 0.1500(3) 0.0637(10) Uani 1 d . . .
H6A H 0.8802 0.8545 0.0702 0.076 Uiso 1 calc R . .
H6B H 0.76 0.7966 0.18 0.076 Uiso 1 calc R . .
C7 C 0.9360(4) 0.6845(3) 0.1881(3) 0.0573(9) Uani 1 d . . .
H7 H 0.8767 0.6234 0.2599 0.069 Uiso 1 calc R . .
C8 C 0.9538(4) 0.6067(4) 0.1104(3) 0.0680(11) Uani 1 d . . .
H8A H 0.9811 0.514 0.1465 0.082 Uiso 1 calc R . .
H8B H 0.8642 0.5977 0.0961 0.082 Uiso 1 calc R . .
C9 C 1.0621(4) 0.6779(4) 0.0017(3) 0.0679(10) Uani 1 d . . .
H9A H 1.0781 0.6179 -0.0396 0.081 Uiso 1 calc R . .
H9B H 1.0268 0.7628 -0.0413 0.081 Uiso 1 calc R . .
C10 C 1.1833(4) 0.7842(4) 0.0931(3) 0.0584(9) Uani 1 d . . .
H10A H 1.1532 0.8766 0.0596 0.07 Uiso 1 calc R . .
H10B H 1.2749 0.7942 0.1039 0.07 Uiso 1 calc R . .
C11 C 1.0794(3) 0.7083(3) 0.2050(3) 0.0531(9) Uani 1 d . . .
C12 C 1.0726(3) 0.7900(3) 0.2814(3) 0.0537(9) Uani 1 d . . .
H12 H 1.1563 0.8546 0.2504 0.064 Uiso 1 calc R . .
C13 C 1.1173(4) 0.7331(5) 0.4652(3) 0.0843(13) Uani 1 d . . .
H13A H 1.2021 0.7925 0.4314 0.127 Uiso 1 calc R . .
H13B H 1.1294 0.6547 0.5275 0.127 Uiso 1 calc R . .
H13C H 1.0414 0.7837 0.4892 0.127 Uiso 1 calc R . .
C14 C 1.1772(4) 0.5835(4) 0.3605(3) 0.0652(10) Uani 1 d . . .
H14 H 1.157 0.4954 0.4245 0.078 Uiso 1 calc R . .
C15 C 1.1333(4) 0.5667(4) 0.2663(3) 0.0652(10) Uani 1 d . . .
H15A H 1.0596 0.4931 0.2946 0.078 Uiso 1 calc R . .
H15B H 1.2125 0.5447 0.2172 0.078 Uiso 1 calc R . .
C16 C 1.3337(4) 0.6243(5) 0.3250(3) 0.0693(11) Uani 1 d . . .
C17 C 1.5572(4) 0.5352(5) 0.3122(4) 0.1014(16) Uani 1 d . . .
H17A H 1.589 0.6061 0.3327 0.122 Uiso 1 calc R . .
H17B H 1.5867 0.5658 0.2325 0.122 Uiso 1 calc R . .
C18 C 1.6169(4) 0.4057(5) 0.3618(4) 0.0996(15) Uani 1 d . . .
H18A H 1.5966 0.3818 0.4399 0.149 Uiso 1 calc R . .
H18B H 1.7168 0.4155 0.3306 0.149 Uiso 1 calc R . .
H18C H 1.5772 0.3338 0.3477 0.149 Uiso 1 calc R . .
C19 C 1.3160(4) 0.7114(4) -0.0567(3) 0.0643(10) Uani 1 d . . .
C20 C 1.5663(4) 0.7884(4) -0.1112(3) 0.0697(11) Uani 1 d . . .
C21 C 1.6458(4) 0.8507(6) -0.0580(4) 0.1028(16) Uani 1 d . . .
H21A H 1.6071 0.9363 -0.0571 0.154 Uiso 1 calc R . .
H21B H 1.7427 0.8685 -0.0992 0.154 Uiso 1 calc R . .
H21C H 1.6384 0.7873 0.0162 0.154 Uiso 1 calc R . .
C22 C 1.6254(5) 0.6554(5) -0.1162(6) 0.130(2) Uani 1 d . . .
H22A H 1.6132 0.5879 -0.0427 0.195 Uiso 1 calc R . .
H22B H 1.7235 0.6722 -0.154 0.195 Uiso 1 calc R . .
H22C H 1.577 0.6212 -0.1552 0.195 Uiso 1 calc R . .
C23 C 1.5650(5) 0.8911(6) -0.2239(4) 0.1183(19) Uani 1 d . . .
H23A H 1.5118 0.8506 -0.2561 0.177 Uiso 1 calc R . .
H23B H 1.6595 0.9152 -0.2699 0.177 Uiso 1 calc R . .
H23C H 1.5228 0.9732 -0.2176 0.177 Uiso 1 calc R . .
 
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_23
    _atom_site_aniso_U_13
    _atom_site_aniso_U_12
S1 0.0617(6) 0.0601(7) 0.0660(6) -0.0131(5) -0.0065(5) 0.0118(5)
S2 0.0741(7) 0.0636(7) 0.0813(7) -0.0363(6) -0.0174(6) 0.0111(5)
N1 0.060(2) 0.064(2) 0.071(2) -0.0372(17) -0.0088(17) -0.0007(15)
N2 0.0630(19) 0.064(2) 0.0578(19) -0.0163(17) -0.0192(15) 0.0209(16)
O1 0.0699(19) 0.065(2) 0.142(3) -0.017(2) -0.0285(19) 0.0073(16)
O2 0.0599(17) 0.0633(18) 0.120(2) -0.0118(16) -0.0250(16) 0.0171(14)
O3 0.0817(19) 0.111(2) 0.0797(19) -0.0592(19) -0.0133(16) 0.0048(17)
O4 0.0625(17) 0.101(2) 0.0786(18) -0.0504(17) -0.0051(15) -0.0015(15)
C1 0.060(3) 0.085(3) 0.098(3) -0.022(3) -0.001(2) 0.023(2)
C2 0.094(3) 0.084(3) 0.107(4) -0.044(3) 0.002(3) 0.032(3)
C3 0.094(3) 0.072(3) 0.094(3) -0.045(3) -0.021(3) 0.030(2)
C4 0.055(2) 0.053(2) 0.063(2) -0.0239(18) -0.0185(18) 0.0130(17)
C5 0.061(2) 0.048(2) 0.065(2) -0.0171(19) -0.0183(19) 0.0111(17)
C6 0.060(2) 0.063(2) 0.065(2) -0.020(2) -0.0184(19) 0.0091(19)
C7 0.058(2) 0.045(2) 0.065(2) -0.0182(18) -0.0136(18) 0.0008(17)
C8 0.066(2) 0.059(2) 0.086(3) -0.034(2) -0.023(2) 0.001(2)
C9 0.067(2) 0.068(3) 0.077(3) -0.039(2) -0.016(2) 0.002(2)
C10 0.061(2) 0.051(2) 0.067(2) -0.0275(19) -0.0155(19) 0.0065(18)
C11 0.052(2) 0.041(2) 0.061(2) -0.0155(18) -0.0131(18) 0.0044(16)
C12 0.054(2) 0.044(2) 0.060(2) -0.0157(18) -0.0169(18) 0.0076(16)
C13 0.092(3) 0.096(3) 0.072(3) -0.031(3) -0.037(2) 0.031(3)
C14 0.055(2) 0.051(2) 0.072(3) -0.007(2) -0.013(2) 0.0104(18)
C15 0.062(2) 0.048(2) 0.082(3) -0.022(2) -0.019(2) 0.0103(18)
C16 0.068(3) 0.054(3) 0.079(3) -0.016(2) -0.024(2) 0.016(2)
C17 0.057(3) 0.082(3) 0.135(4) -0.013(3) -0.020(3) 0.011(2)
C18 0.072(3) 0.091(3) 0.119(4) -0.020(3) -0.028(3) 0.020(3)
C19 0.073(3) 0.058(2) 0.062(2) -0.026(2) -0.014(2) 0.006(2)
C20 0.062(2) 0.067(3) 0.071(3) -0.025(2) -0.004(2) 0.008(2)
C21 0.067(3) 0.141(4) 0.104(3) -0.056(3) -0.013(3) -0.011(3)
C22 0.087(3) 0.098(4) 0.197(6) -0.068(4) -0.010(4) 0.023(3)
C23 0.101(4) 0.126(4) 0.090(3) 0.003(3) -0.025(3) -0.020(3)
 
 
#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
 
_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_distance
    _geom_bond_site_symmetry_2
    _geom_bond_publ_flag
S1 C1 1.800(4) . ?
S1 C4 1.824(4) . ?
S2 C3 1.810(4) . ?
S2 C4 1.840(4) . ?
N1 C19 1.354(5) . ?
N1 C9 1.462(4) . ?
N1 C10 1.466(4) . ?
N2 C14 1.444(4) . ?
N2 C13 1.458(5) . ?
N2 C12 1.459(4) . ?
O1 C16 1.196(4) . ?
O2 C16 1.320(4) . ?
O2 C17 1.444(5) . ?
O3 C19 1.202(4) . ?
O4 C19 1.340(4) . ?
O4 C20 1.459(4) . ?
C1 C2 1.511(6) . ?
C2 C3 1.505(6) . ?
C4 C5 1.521(5) . ?
C4 C12 1.551(4) . ?
C5 C6 1.519(5) . ?
C6 C7 1.536(5) . ?
C7 C8 1.528(5) . ?
C7 C11 1.538(5) . ?
C8 C9 1.512(5) . ?
C10 C11 1.527(5) . ?
C11 C15 1.550(5) . ?
C11 C12 1.558(5) . ?
C14 C16 1.521(5) . ?
C14 C15 1.523(5) . ?
C17 C18 1.444(5) . ?
C20 C21 1.499(6) . ?
C20 C22 1.502(6) . ?
C20 C23 1.504(6) . ?
 
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle_publ_flag
C1 S1 C4 100.88(18) . . ?
C3 S2 C4 102.06(18) . . ?
C19 N1 C9 118.7(3) . . ?
C19 N1 C10 122.8(3) . . ?
C9 N1 C10 115.3(3) . . ?
C14 N2 C13 114.4(3) . . ?
C14 N2 C12 108.2(3) . . ?
C13 N2 C12 117.5(3) . . ?
C16 O2 C17 116.8(3) . . ?
C19 O4 C20 123.2(3) . . ?
C2 C1 S1 114.8(3) . . ?
C3 C2 C1 113.3(4) . . ?
C2 C3 S2 114.2(3) . . ?
C5 C4 C12 108.7(3) . . ?
C5 C4 S1 113.2(2) . . ?
C12 C4 S1 108.5(2) . . ?
C5 C4 S2 108.6(2) . . ?
C12 C4 S2 106.5(2) . . ?
S1 C4 S2 111.18(18) . . ?
C6 C5 C4 114.3(3) . . ?
C5 C6 C7 113.7(3) . . ?
C8 C7 C6 112.6(3) . . ?
C8 C7 C11 109.4(3) . . ?
C6 C7 C11 113.2(3) . . ?
C9 C8 C7 113.2(3) . . ?
N1 C9 C8 111.4(3) . . ?
N1 C10 C11 112.2(3) . . ?
C10 C11 C7 109.5(3) . . ?
C10 C11 C15 110.3(3) . . ?
C7 C11 C15 109.6(3) . . ?
C10 C11 C12 110.0(3) . . ?
C7 C11 C12 113.3(3) . . ?
C15 C11 C12 104.1(3) . . ?
N2 C12 C4 114.1(3) . . ?
N2 C12 C11 104.3(3) . . ?
C4 C12 C11 115.0(3) . . ?
N2 C14 C16 115.8(3) . . ?
N2 C14 C15 103.1(3) . . ?
C16 C14 C15 109.7(3) . . ?
C14 C15 C11 105.6(3) . . ?
O1 C16 O2 123.1(4) . . ?
O1 C16 C14 126.2(3) . . ?
O2 C16 C14 110.7(4) . . ?
O2 C17 C18 108.3(4) . . ?
O3 C19 O4 125.5(4) . . ?
O3 C19 N1 123.7(4) . . ?
O4 C19 N1 110.9(3) . . ?
O4 C20 C21 102.9(3) . . ?
O4 C20 C22 110.4(4) . . ?
C21 C20 C22 111.2(4) . . ?
O4 C20 C23 110.2(3) . . ?
C21 C20 C23 110.5(4) . . ?
C22 C20 C23 111.4(4) . . ?