data_global
_audit_creation_method                  'APEX2 v2014.9-0'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_I
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C27 H28 N2 O5 S2'
_chemical_formula_iupac                 ?
_chemical_formula_weight                524.63

_chemical_melting_point                 ?

_space_group_crystal_system             triclinic
_space_group_name_H-M_alt               'P -1'
_space_group_name_Hall                  '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'

_cell_length_a                          9.475(2)
_cell_length_b                          10.144(2)
_cell_length_c                          13.660(3)
_cell_angle_alpha                       98.118(3)
_cell_angle_beta                        91.348(3)
_cell_angle_gamma                       100.871(3)
_cell_volume                            1274.7(5)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           110
_cell_measurement_theta_min             2.7372
_cell_measurement_theta_max             25.1036
_cell_measurement_temperature           173

_exptl_crystal_description              Prismatic
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.300
_exptl_crystal_size_mid                 0.200
_exptl_crystal_size_min                 0.200
_exptl_crystal_density_diffrn           1.367
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    552

_exptl_absorpt_coefficient_mu           0.250
_exptl_absorpt_correction_type          empirical
_exptl_absorpt_process_details          'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min         0.87
_exptl_absorpt_correction_T_max         0.95

_exptl_special_details                  'SADABS (Sheldrick 1996)' 

_diffrn_ambient_temperature             173

_diffrn_source                          'fine-focus sealed tube'
_diffrn_source_type                     ?

_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         graphite

_diffrn_measurement_device_type         'Bruker APEXII CCD area detector'
_diffrn_measurement_method              'Phi and Omega scans'

_diffrn_detector_area_resol_mean        8.3333

_diffrn_reflns_number                   7413
_diffrn_reflns_av_R_equivalents         0.0257
_diffrn_reflns_av_unetI/netI            0.0752
_diffrn_reflns_theta_min                1.51
_diffrn_reflns_theta_max                27.572
_diffrn_reflns_theta_full               27.500
_diffrn_measured_fraction_theta_max     0.948
_diffrn_measured_fraction_theta_full    0.983
_diffrn_reflns_limit_h_min              -8
_diffrn_reflns_limit_h_max              12
_diffrn_reflns_limit_k_min              -10
_diffrn_reflns_limit_k_max              13
_diffrn_reflns_limit_l_min              -17
_diffrn_reflns_limit_l_max              17

_refine_special_details                 
;
;

_reflns_number_total                    5602
_reflns_number_gt                       3559
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0892
_refine_ls_R_factor_gt                  0.0508
_refine_ls_wR_factor_gt                 0.1031
_refine_ls_wR_factor_ref                0.1223
_refine_ls_goodness_of_fit_ref          1.015
_refine_ls_restrained_S_all             1.015
_refine_ls_number_reflns                5602
_refine_ls_number_parameters            330
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0446P)²+0.1253P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.264
_refine_diff_density_min                -0.440
_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'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 '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'

_computing_data_collection              'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement              'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction               'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution           'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement         'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics           'XSHEL (Bruker AXS,2002)'
_computing_publication_material         'XCIF (Bruker AXS, 2001)'

loop_
    _atom_site_type_symbol
    _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_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.43583(7) 0.86224(7) 0.78446(5) 0.02802(17) Uani d . . . 1 . .
    S S2 0.14278(7) 0.75030(7) 0.84053(5) 0.02953(18) Uani d . . . 1 . .
    O O3 0.40847(19) 0.97866(17) 0.84746(13) 0.0342(5) Uani d . . . 1 . .
    O O4 0.2096(2) 0.77469(19) 0.93771(13) 0.0370(5) Uani d . . . 1 . .
    O O2 0.49461(18) 0.87483(19) 0.69075(13) 0.0359(5) Uani d . . . 1 . .
    O O5 0.04609(19) 0.62462(18) 0.80636(15) 0.0399(5) Uani d . . . 1 . .
    O O1 0.2577(2) 0.2882(2) 0.44911(14) 0.0485(6) Uani d . . . 1 . .
    N N2 0.2754(2) 0.7550(2) 0.75950(15) 0.0262(5) Uani d . . . 1 . .
    N N1 0.2623(2) 0.4586(2) 0.57436(15) 0.0278(5) Uani d . . . 1 . .
    C C1 0.2930(3) 0.5303(3) 0.67017(19) 0.0274(6) Uani d . . . 1 . .
    H H1 0.3315 0.4967 0.7243 0.033 Uiso calc U . R 1 . .
    C C3 0.2037(3) 0.6662(3) 0.57818(18) 0.0252(6) Uani d . . . 1 . .
    C C21 0.0550(3) 0.8845(3) 0.82480(19) 0.0277(6) Uani d . . . 1 . .
    C C22 0.0862(3) 1.0031(3) 0.89200(19) 0.0308(6) Uani d . . . 1 . .
    H H22 0.1625 1.0169 0.941 0.037 Uiso calc U . R 1 . .
    C C8 0.2039(3) 0.5435(3) 0.51666(19) 0.0263(6) Uani d . . . 1 . .
    C C2 0.2595(2) 0.6538(3) 0.67387(18) 0.0254(6) Uani d . . . 1 . .
    C C7 0.1491(3) 0.5208(3) 0.41927(19) 0.0297(6) Uani d . . . 1 . .
    H H7 0.1477 0.4369 0.3779 0.036 Uiso calc U . R 1 . .
    C C14 0.5389(3) 0.7740(3) 0.85067(19) 0.0279(6) Uani d . . . 1 . .
    C C24 -0.1078(3) 1.0825(3) 0.8144(2) 0.0325(6) Uani d . . . 1 . .
    C C9 0.2863(3) 0.3286(3) 0.5363(2) 0.0318(6) Uani d . . . 1 . .
    C C4 0.1522(3) 0.7705(3) 0.5414(2) 0.0331(6) Uani d . . . 1 . .
    H H4 0.1533 0.8547 0.5824 0.04 Uiso calc U . R 1 . .
    C C27 -0.0517(3) 0.8655(3) 0.7509(2) 0.0331(6) Uani d . . . 1 . .
    H H27 -0.07 0.7849 0.704 0.04 Uiso calc U . R 1 . .
    C C5 0.0996(3) 0.7488(3) 0.4442(2) 0.0373(7) Uani d . . . 1 . .
    H H5 0.0651 0.819 0.4174 0.045 Uiso calc U . R 1 . .
    C C23 0.0033(3) 1.1013(3) 0.8860(2) 0.0340(7) Uani d . . . 1 . .
    H H23 0.023 1.183 0.9318 0.041 Uiso calc U . R 1 . .
    C C6 0.0968(3) 0.6244(3) 0.3850(2) 0.0350(7) Uani d . . . 1 . .
    H H6 0.0576 0.6107 0.3189 0.042 Uiso calc U . R 1 . .
    C C15 0.6137(3) 0.6837(3) 0.7988(2) 0.0351(7) Uani d . . . 1 . .
    H H15 0.6131 0.6731 0.7285 0.042 Uiso calc U . R 1 . .
    C C10 0.3484(3) 0.2428(3) 0.6045(2) 0.0314(6) Uani d . . . 1 . .
    C C20 0.5419(3) 0.7923(3) 0.9523(2) 0.0352(7) Uani d . . . 1 . .
    H H20 0.4921 0.8556 0.9874 0.042 Uiso calc U . R 1 . .
    C C26 -0.1318(3) 0.9654(3) 0.7461(2) 0.0365(7) Uani d . . . 1 . .
    H H26 -0.2046 0.9533 0.6948 0.044 Uiso calc U . R 1 . .
    C C17 0.6913(3) 0.6243(3) 0.9532(2) 0.0405(7) Uani d . . . 1 . .
    C C16 0.6891(3) 0.6094(3) 0.8510(2) 0.0390(7) Uani d . . . 1 . .
    H H16 0.7403 0.5473 0.8159 0.047 Uiso calc U . R 1 . .
    C C12 0.2492(3) 0.2082(3) 0.6880(2) 0.0405(7) Uani d . . . 1 . .
    H H12A 0.2934 0.1546 0.7299 0.061 Uiso calc U . R 1 . .
    H H12B 0.1562 0.1556 0.6596 0.061 Uiso calc U . R 1 . .
    H H12C 0.2348 0.2923 0.728 0.061 Uiso calc U . R 1 . .
    C C19 0.6186(3) 0.7174(3) 1.0028(2) 0.0434(8) Uani d . . . 1 . .
    H H19 0.6213 0.7302 1.0731 0.052 Uiso calc U . R 1 . .
    C C13 0.3592(4) 0.1096(3) 0.5397(2) 0.0522(9) Uani d . . . 1 . .
    H H13A 0.4248 0.1285 0.4868 0.078 Uiso calc U . R 1 . .
    H H13B 0.2637 0.065 0.5106 0.078 Uiso calc U . R 1 . .
    H H13C 0.3961 0.05 0.5803 0.078 Uiso calc U . R 1 . .
    C C25 -0.2047(3) 1.1849(3) 0.8145(2) 0.0487(9) Uani d . . . 1 . .
    H H25A -0.2832 1.1636 0.8586 0.073 Uiso calc U . R 1 . .
    H H25B -0.2447 1.1814 0.7472 0.073 Uiso calc U . R 1 . .
    H H25C -0.149 1.2761 0.8378 0.073 Uiso calc U . R 1 . .
    C C11 0.5002(3) 0.3117(3) 0.6449(3) 0.0540(9) Uani d . . . 1 . .
    H H11A 0.5597 0.3358 0.59 0.081 Uiso calc U . R 1 . .
    H H11B 0.5427 0.2494 0.6798 0.081 Uiso calc U . R 1 . .
    H H11C 0.4956 0.394 0.6909 0.081 Uiso calc U . R 1 . .
    C C18 0.7715(4) 0.5398(3) 1.0081(3) 0.0640(10) Uani d . . . 1 . .
    H H18A 0.7185 0.4458 0.9988 0.096 Uiso calc U . R 1 . .
    H H18B 0.7807 0.5763 1.0788 0.096 Uiso calc U . R 1 . .
    H H18C 0.8675 0.5424 0.9823 0.096 Uiso calc U . R 1 . .


_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
    S1 O2 . 1.4205(18) ?
    S1 O3 . 1.4288(18) ?
    S1 N2 . 1.691(2) ?
    S1 C14 . 1.758(2) ?
    S2 O4 . 1.4258(19) ?
    S2 O5 . 1.433(2) ?
    S2 N2 . 1.692(2) ?
    S2 C21 . 1.759(3) ?
    O1 C9 . 1.210(3) ?
    N2 C2 . 1.428(3) ?
    N1 C1 . 1.400(3) ?
    N1 C9 . 1.410(3) ?
    N1 C8 . 1.421(3) ?
    C1 C2 . 1.344(3) ?
    C1 H1 . 0.95 ?
    C3 C4 . 1.394(3) ?
    C3 C8 . 1.400(3) ?
    C3 C2 . 1.429(3) ?
    C21 C27 . 1.379(3) ?
    C21 C22 . 1.385(3) ?
    C22 C23 . 1.391(3) ?
    C22 H22 . 0.95 ?
    C8 C7 . 1.389(3) ?
    C7 C6 . 1.376(3) ?
    C7 H7 . 0.95 ?
    C14 C20 . 1.373(4) ?
    C14 C15 . 1.388(3) ?
    C24 C26 . 1.382(4) ?
    C24 C23 . 1.387(4) ?
    C24 C25 . 1.510(3) ?
    C9 C10 . 1.538(3) ?
    C4 C5 . 1.380(4) ?
    C4 H4 . 0.95 ?
    C27 C26 . 1.383(3) ?
    C27 H27 . 0.95 ?
    C5 C6 . 1.395(4) ?
    C5 H5 . 0.95 ?
    C23 H23 . 0.95 ?
    C6 H6 . 0.95 ?
    C15 C16 . 1.385(4) ?
    C15 H15 . 0.95 ?
    C10 C13 . 1.528(4) ?
    C10 C11 . 1.529(4) ?
    C10 C12 . 1.533(3) ?
    C20 C19 . 1.383(4) ?
    C20 H20 . 0.95 ?
    C26 H26 . 0.95 ?
    C17 C16 . 1.382(4) ?
    C17 C19 . 1.383(4) ?
    C17 C18 . 1.508(4) ?
    C16 H16 . 0.95 ?
    C12 H12A . 0.98 ?
    C12 H12B . 0.98 ?
    C12 H12C . 0.98 ?
    C19 H19 . 0.95 ?
    C13 H13A . 0.98 ?
    C13 H13B . 0.98 ?
    C13 H13C . 0.98 ?
    C25 H25A . 0.98 ?
    C25 H25B . 0.98 ?
    C25 H25C . 0.98 ?
    C11 H11A . 0.98 ?
    C11 H11B . 0.98 ?
    C11 H11C . 0.98 ?
    C18 H18A . 0.98 ?
    C18 H18B . 0.98 ?
    C18 H18C . 0.98 ?

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
    O2 S1 O3 . . 120.63(11) ?
    O2 S1 N2 . . 105.21(11) ?
    O3 S1 N2 . . 106.38(10) ?
    O2 S1 C14 . . 109.12(12) ?
    O3 S1 C14 . . 109.78(12) ?
    N2 S1 C14 . . 104.39(11) ?
    O4 S2 O5 . . 120.25(12) ?
    O4 S2 N2 . . 107.34(11) ?
    O5 S2 N2 . . 104.09(11) ?
    O4 S2 C21 . . 109.03(12) ?
    O5 S2 C21 . . 108.53(12) ?
    N2 S2 C21 . . 106.78(11) ?
    C2 N2 S1 . . 118.35(16) ?
    C2 N2 S2 . . 119.25(16) ?
    S1 N2 S2 . . 121.85(12) ?
    C1 N1 C9 . . 128.9(2) ?
    C1 N1 C8 . . 107.3(2) ?
    C9 N1 C8 . . 123.7(2) ?
    C2 C1 N1 . . 109.7(2) ?
    C2 C1 H1 . . 125.2 ?
    N1 C1 H1 . . 125.2 ?
    C4 C3 C8 . . 120.3(2) ?
    C4 C3 C2 . . 132.5(2) ?
    C8 C3 C2 . . 107.2(2) ?
    C27 C21 C22 . . 121.3(2) ?
    C27 C21 S2 . . 119.3(2) ?
    C22 C21 S2 . . 119.1(2) ?
    C21 C22 C23 . . 118.4(3) ?
    C21 C22 H22 . . 120.8 ?
    C23 C22 H22 . . 120.8 ?
    C7 C8 C3 . . 121.3(2) ?
    C7 C8 N1 . . 131.5(2) ?
    C3 C8 N1 . . 107.2(2) ?
    C1 C2 N2 . . 125.6(2) ?
    C1 C2 C3 . . 108.6(2) ?
    N2 C2 C3 . . 125.8(2) ?
    C6 C7 C8 . . 117.4(3) ?
    C6 C7 H7 . . 121.3 ?
    C8 C7 H7 . . 121.3 ?
    C20 C14 C15 . . 120.9(2) ?
    C20 C14 S1 . . 120.0(2) ?
    C15 C14 S1 . . 119.1(2) ?
    C26 C24 C23 . . 118.6(2) ?
    C26 C24 C25 . . 120.9(3) ?
    C23 C24 C25 . . 120.5(3) ?
    O1 C9 N1 . . 117.9(2) ?
    O1 C9 C10 . . 121.8(2) ?
    N1 C9 C10 . . 120.3(2) ?
    C5 C4 C3 . . 118.5(3) ?
    C5 C4 H4 . . 120.8 ?
    C3 C4 H4 . . 120.8 ?
    C21 C27 C26 . . 119.1(3) ?
    C21 C27 H27 . . 120.5 ?
    C26 C27 H27 . . 120.5 ?
    C4 C5 C6 . . 120.3(3) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    C24 C23 C22 . . 121.3(3) ?
    C24 C23 H23 . . 119.3 ?
    C22 C23 H23 . . 119.3 ?
    C7 C6 C5 . . 122.2(3) ?
    C7 C6 H6 . . 118.9 ?
    C5 C6 H6 . . 118.9 ?
    C16 C15 C14 . . 119.0(3) ?
    C16 C15 H15 . . 120.5 ?
    C14 C15 H15 . . 120.5 ?
    C13 C10 C11 . . 107.7(2) ?
    C13 C10 C12 . . 107.7(2) ?
    C11 C10 C12 . . 111.5(2) ?
    C13 C10 C9 . . 106.3(2) ?
    C11 C10 C9 . . 111.1(2) ?
    C12 C10 C9 . . 112.2(2) ?
    C14 C20 C19 . . 119.1(3) ?
    C14 C20 H20 . . 120.5 ?
    C19 C20 H20 . . 120.5 ?
    C24 C26 C27 . . 121.2(3) ?
    C24 C26 H26 . . 119.4 ?
    C27 C26 H26 . . 119.4 ?
    C16 C17 C19 . . 118.5(3) ?
    C16 C17 C18 . . 120.0(3) ?
    C19 C17 C18 . . 121.5(3) ?
    C17 C16 C15 . . 121.1(3) ?
    C17 C16 H16 . . 119.4 ?
    C15 C16 H16 . . 119.4 ?
    C10 C12 H12A . . 109.5 ?
    C10 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C10 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C20 C19 C17 . . 121.4(3) ?
    C20 C19 H19 . . 119.3 ?
    C17 C19 H19 . . 119.3 ?
    C10 C13 H13A . . 109.5 ?
    C10 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C10 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C24 C25 H25A . . 109.5 ?
    C24 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C24 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C17 C18 H18A . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?



