# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535552'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24  H26  O4  S2'
_chemical_formula_sum            'C24 H26 O4 S2'
_chemical_formula_weight         442.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.0710(3)
_cell_length_b                   15.0757(9)
_cell_length_c                   25.2963(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.595(3)
_cell_angle_gamma                90
_cell_volume                     2312.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7929
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      67.87

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    2.305
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS SADABS-2012/1, Bruker Inc., 
Madison, Wisconsin, USA. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22816
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.414
_diffrn_reflns_theta_max         67.863
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4187
_reflns_number_gt                3467
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.5475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00030(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4187
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.00679(8) 0.63030(3) -0.03180(2) 0.04950(14) Uani 1 1 d . . . . .
S2 S 0.43411(7) 0.60729(3) 0.03231(2) 0.04470(13) Uani 1 1 d . . . . .
O1 O -0.9396(2) 0.70799(9) -0.32205(5) 0.0628(4) Uani 1 1 d . . . . .
O2 O -1.2426(2) 0.63239(8) -0.30364(5) 0.0549(3) Uani 1 1 d . . . . .
O3 O 1.4149(2) 0.67544(8) 0.31318(5) 0.0585(3) Uani 1 1 d . . . . .
O4 O 1.70688(19) 0.59078(8) 0.29643(5) 0.0519(3) Uani 1 1 d . . . . .
C1 C 0.1486(3) 0.72635(10) -0.01516(6) 0.0421(4) Uani 1 1 d . . . . .
C2 C 0.3482(3) 0.71556(10) 0.01376(6) 0.0406(4) Uani 1 1 d . . . . .
C3 C 0.4772(3) 0.78941(12) 0.02655(7) 0.0553(5) Uani 1 1 d . . . . .
H3 H 0.6148 0.7821 0.0454 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4062(4) 0.87315(12) 0.01198(8) 0.0698(6) Uani 1 1 d . . . . .
H4 H 0.4952 0.9233 0.0207 0.084 Uiso 1 1 calc R U . . .
C5 C 0.2065(4) 0.88405(12) -0.01522(8) 0.0688(6) Uani 1 1 d . . . . .
H5 H 0.1569 0.9419 -0.0246 0.083 Uiso 1 1 calc R U . . .
C6 C 0.0776(3) 0.81111(12) -0.02897(7) 0.0555(5) Uani 1 1 d . . . . .
H6 H -0.0598 0.8191 -0.0479 0.067 Uiso 1 1 calc R U . . .
C7 C -0.1448(3) 0.66269(11) -0.09061(6) 0.0448(4) Uani 1 1 d . . . . .
H7 H -0.0778 0.7053 -0.1124 0.054 Uiso 1 1 calc R U . . .
C8 C -0.3410(3) 0.62977(10) -0.10612(6) 0.0430(4) Uani 1 1 d . . . . .
H8 H -0.4140 0.5911 -0.0830 0.052 Uiso 1 1 calc R U . . .
C9 C -0.4457(3) 0.65083(10) -0.15661(6) 0.0413(4) Uani 1 1 d . . . . .
H9 H -0.3673 0.6880 -0.1795 0.050 Uiso 1 1 calc R U . . .
C10 C -0.6454(3) 0.62223(10) -0.17401(6) 0.0416(4) Uani 1 1 d . . . . .
H10 H -0.7230 0.5826 -0.1524 0.050 Uiso 1 1 calc R U . . .
C11 C -0.7471(3) 0.64888(10) -0.22386(6) 0.0408(4) Uani 1 1 d . . . . .
H11 H -0.6632 0.6860 -0.2457 0.049 Uiso 1 1 calc R U . . .
C12 C -0.9481(3) 0.62627(10) -0.24224(6) 0.0432(4) Uani 1 1 d . . . . .
H12 H -1.0350 0.5875 -0.2222 0.052 Uiso 1 1 calc R U . . .
C13 C -1.0369(3) 0.66052(10) -0.29306(6) 0.0421(4) Uani 1 1 d . . . . .
C14 C -1.3452(4) 0.65951(14) -0.35388(8) 0.0710(6) Uani 1 1 d . . . . .
H14A H -1.2313 0.6671 -0.3803 0.085 Uiso 1 1 calc R U . . .
H14B H -1.4214 0.7170 -0.3498 0.085 Uiso 1 1 calc R U . . .
C15 C -1.5034(3) 0.59198(15) -0.37185(8) 0.0733(6) Uani 1 1 d . . . . .
H15A H -1.5832 0.6125 -0.4041 0.110 Uiso 1 1 calc R U . . .
H15B H -1.6082 0.5812 -0.3442 0.110 Uiso 1 1 calc R U . . .
H15C H -1.4250 0.5369 -0.3793 0.110 Uiso 1 1 calc R U . . .
C16 C 0.5925(3) 0.63110(10) 0.09004(6) 0.0423(4) Uani 1 1 d . . . . .
H16 H 0.5386 0.6746 0.1133 0.051 Uiso 1 1 calc R U . . .
C17 C 0.7838(3) 0.59209(10) 0.10343(6) 0.0419(4) Uani 1 1 d . . . . .
H17 H 0.8442 0.5502 0.0801 0.050 Uiso 1 1 calc R U . . .
C18 C 0.9002(3) 0.61247(10) 0.15266(6) 0.0415(4) Uani 1 1 d . . . . .
H18 H 0.8288 0.6512 0.1760 0.050 Uiso 1 1 calc R U . . .
C19 C 1.0997(3) 0.58213(11) 0.16885(6) 0.0420(4) Uani 1 1 d . . . . .
H19 H 1.1712 0.5402 0.1475 0.050 Uiso 1 1 calc R U . . .
C20 C 1.2090(3) 0.61087(10) 0.21736(6) 0.0411(4) Uani 1 1 d . . . . .
H20 H 1.1311 0.6513 0.2385 0.049 Uiso 1 1 calc R U . . .
C21 C 1.4087(3) 0.58643(10) 0.23570(6) 0.0430(4) Uani 1 1 d . . . . .
H21 H 1.4906 0.5448 0.2164 0.052 Uiso 1 1 calc R U . . .
C22 C 1.5041(3) 0.62302(10) 0.28538(7) 0.0430(4) Uani 1 1 d . . . . .
C23 C 1.8140(4) 0.62082(13) 0.34537(8) 0.0686(6) Uani 1 1 d . . . . .
H23A H 1.7062 0.6229 0.3736 0.082 Uiso 1 1 calc R U . . .
H23B H 1.8740 0.6812 0.3408 0.082 Uiso 1 1 calc R U . . .
C24 C 1.9956(3) 0.55827(14) 0.36054(8) 0.0652(5) Uani 1 1 d . . . . .
H24A H 2.0914 0.5507 0.3307 0.098 Uiso 1 1 calc R U . . .
H24B H 1.9333 0.5007 0.3699 0.098 Uiso 1 1 calc R U . . .
H24C H 2.0819 0.5822 0.3910 0.098 Uiso 1 1 calc R U . . .


_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 C7 1.7436(16) . ?
S1 C1 1.7687(16) . ?
S2 C16 1.7490(16) . ?
S2 C2 1.7704(16) . ?
O1 C13 1.1991(19) . ?
O2 C13 1.3347(19) . ?
O2 C14 1.449(2) . ?
O3 C22 1.2027(19) . ?
O4 C22 1.341(2) . ?
O4 C23 1.445(2) . ?
C1 C6 1.388(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.333(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.436(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.342(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.436(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.330(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.465(2) . ?
C12 H12 0.9500 . ?
C14 C15 1.458(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.332(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.437(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.341(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.435(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.330(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.467(2) . ?
C21 H21 0.9500 . ?
C23 C24 1.488(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C7 S1 C1 101.79(8) . . ?
C16 S2 C2 100.16(7) . . ?
C13 O2 C14 116.58(14) . . ?
C22 O4 C23 115.98(14) . . ?
C6 C1 C2 119.43(15) . . ?
C6 C1 S1 122.51(14) . . ?
C2 C1 S1 118.05(12) . . ?
C3 C2 C1 119.66(15) . . ?
C3 C2 S2 121.34(13) . . ?
C1 C2 S2 118.99(12) . . ?
C4 C3 C2 120.34(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.01(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.39(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.13(18) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 S1 122.38(13) . . ?
C8 C7 H7 118.8 . . ?
S1 C7 H7 118.8 . . ?
C7 C8 C9 122.23(16) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C10 C9 C8 125.29(16) . . ?
C10 C9 H9 117.4 . . ?
C8 C9 H9 117.4 . . ?
C9 C10 C11 122.96(15) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C12 C11 C10 125.88(16) . . ?
C12 C11 H11 117.1 . . ?
C10 C11 H11 117.1 . . ?
C11 C12 C13 120.76(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
O1 C13 O2 123.32(15) . . ?
O1 C13 C12 125.11(15) . . ?
O2 C13 C12 111.58(14) . . ?
O2 C14 C15 109.11(16) . . ?
O2 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
O2 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S2 124.18(13) . . ?
C17 C16 H16 117.9 . . ?
S2 C16 H16 117.9 . . ?
C16 C17 C18 120.99(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 126.41(16) . . ?
C19 C18 H18 116.8 . . ?
C17 C18 H18 116.8 . . ?
C18 C19 C20 122.29(15) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 126.39(16) . . ?
C21 C20 H20 116.8 . . ?
C19 C20 H20 116.8 . . ?
C20 C21 C22 120.84(15) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
O3 C22 O4 123.34(15) . . ?
O3 C22 C21 125.24(15) . . ?
O4 C22 C21 111.41(14) . . ?
O4 C23 C24 108.77(16) . . ?
O4 C23 H23A 109.9 . . ?
C24 C23 H23A 109.9 . . ?
O4 C23 H23B 109.9 . . ?
C24 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 S1 C1 C6 30.12(17) . . . . ?
C7 S1 C1 C2 -151.01(14) . . . . ?
C6 C1 C2 C3 -2.5(3) . . . . ?
S1 C1 C2 C3 178.58(13) . . . . ?
C6 C1 C2 S2 178.69(13) . . . . ?
S1 C1 C2 S2 -0.21(19) . . . . ?
C16 S2 C2 C3 29.35(16) . . . . ?
C16 S2 C2 C1 -151.88(14) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
S2 C2 C3 C4 -179.59(15) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
S1 C1 C6 C5 -179.59(15) . . . . ?
C1 S1 C7 C8 -151.33(15) . . . . ?
S1 C7 C8 C9 -174.60(12) . . . . ?
C7 C8 C9 C10 -177.88(16) . . . . ?
C8 C9 C10 C11 176.83(15) . . . . ?
C9 C10 C11 C12 -176.70(16) . . . . ?
C10 C11 C12 C13 177.72(14) . . . . ?
C14 O2 C13 O1 2.2(3) . . . . ?
C14 O2 C13 C12 -177.89(15) . . . . ?
C11 C12 C13 O1 1.9(3) . . . . ?
C11 C12 C13 O2 -178.06(15) . . . . ?
C13 O2 C14 C15 150.45(18) . . . . ?
C2 S2 C16 C17 -139.44(15) . . . . ?
S2 C16 C17 C18 -177.36(12) . . . . ?
C16 C17 C18 C19 -175.30(16) . . . . ?
C17 C18 C19 C20 175.86(14) . . . . ?
C18 C19 C20 C21 -177.90(16) . . . . ?
C19 C20 C21 C22 178.17(14) . . . . ?
C23 O4 C22 O3 1.7(2) . . . . ?
C23 O4 C22 C21 -178.45(15) . . . . ?
C20 C21 C22 O3 0.6(3) . . . . ?
C20 C21 C22 O4 -179.23(14) . . . . ?
C22 O4 C23 C24 161.05(16) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535554'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 O4 S2, C12 H10 O4 S2, Na, 2 (H2 O)'
_chemical_formula_sum            'C24 H23 Na O10 S4'
_chemical_formula_weight         622.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.29580(10)
_cell_length_b                   40.1116(9)
_cell_length_c                   10.5256(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.680(2)
_cell_angle_gamma                90
_cell_volume                     2634.23(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3598
_cell_measurement_theta_min      4.38
_cell_measurement_theta_max      68.18

_exptl_crystal_description       platelet
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.983
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            26845
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.203
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4834
_reflns_number_gt                3506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'bruker APEX2'
_computing_cell_refinement       'bruker SAINT'
_computing_data_reduction        'bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.8582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4834
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.10013(12) 0.69013(2) 1.17351(7) 0.02944(19) Uani 1 1 d . . . . .
S2 S 0.50432(12) 0.68607(2) 1.00589(8) 0.02947(19) Uani 1 1 d . . . . .
O1 O -0.1076(4) 0.57531(6) 1.1016(3) 0.0472(7) Uani 1 1 d . . . . .
O2 O 0.2481(4) 0.58024(6) 1.1144(3) 0.0425(6) Uani 1 1 d . . . . .
H2 H 0.2604(7) 0.5591(11) 1.1374(12) 0.064 Uiso 1 1 d R U . . .
O3 O 0.1210(3) 0.58370(5) 0.8139(2) 0.0378(6) Uani 1 1 d . . . . .
O4 O 0.4513(3) 0.60518(6) 0.8378(2) 0.0374(6) Uani 1 1 d . . . . .
H4A H 0.4688(8) 0.5861(8) 0.782(2) 0.056 Uiso 1 1 d R U . . .
C1 C 0.1183(5) 0.71552(7) 1.0388(3) 0.0258(6) Uani 1 1 d . . . . .
C2 C 0.2918(5) 0.71449(7) 0.9675(3) 0.0263(7) Uani 1 1 d . . . . .
C3 C 0.3033(5) 0.73764(8) 0.8709(3) 0.0334(7) Uani 1 1 d . . . . .
H3 H 0.4186 0.7367 0.8212 0.040 Uiso 1 1 calc R U . . .
C4 C 0.1483(6) 0.76212(8) 0.8461(3) 0.0418(9) Uani 1 1 d . . . . .
H4 H 0.1586 0.7781 0.7807 0.050 Uiso 1 1 calc R U . . .
C5 C -0.0206(6) 0.76323(8) 0.9164(3) 0.0391(8) Uani 1 1 d . . . . .
H5 H -0.1264 0.7801 0.8995 0.047 Uiso 1 1 calc R U . . .
C6 C -0.0380(5) 0.74004(8) 1.0113(3) 0.0331(7) Uani 1 1 d . . . . .
H6 H -0.1569 0.7408 1.0581 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1983(5) 0.64969(7) 1.1348(3) 0.0255(6) Uani 1 1 d . . . . .
H7 H 0.2536 0.6372 1.2147 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0451(5) 0.62706(7) 1.0420(3) 0.0266(7) Uani 1 1 d . . . . .
H8 H -0.1029 0.6363 1.0215 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1906(4) 0.63402(7) 0.9355(3) 0.0241(6) Uani 1 1 d . . . . .
H9 H 0.1262 0.6522 0.8778 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3631(5) 0.64872(7) 1.0383(3) 0.0238(6) Uani 1 1 d . . . . .
H10 H 0.4708 0.6309 1.0657 0.029 Uiso 1 1 calc R U . . .
C11 C 0.0489(5) 0.59146(8) 1.0879(3) 0.0304(7) Uani 1 1 d . . . . .
C12 C 0.2483(5) 0.60512(7) 0.8565(3) 0.0271(7) Uani 1 1 d . . . . .
S3 S 0.39437(12) 0.62721(2) 0.50653(8) 0.02949(19) Uani 1 1 d . . . . .
S4 S 0.75856(12) 0.63579(2) 0.32296(7) 0.02749(18) Uani 1 1 d . . . . .
O5 O 0.5216(3) 0.55025(5) 0.7090(2) 0.0308(5) Uani 1 1 d . . . . .
O6 O 0.8132(3) 0.52456(5) 0.6612(2) 0.0275(5) Uani 1 1 d . . . . .
O7 O 0.7934(3) 0.52397(5) 0.3666(2) 0.0319(5) Uani 1 1 d . . . . .
O8 O 1.1318(3) 0.53428(5) 0.4534(2) 0.0346(5) Uani 1 1 d . . . . .
H8A H 1.1529(10) 0.5135(9) 0.4215(15) 0.052 Uiso 1 1 d R U . . .
C13 C 0.6145(5) 0.65402(7) 0.5501(3) 0.0261(6) Uani 1 1 d . . . . .
C14 C 0.7757(5) 0.65704(7) 0.4709(3) 0.0250(6) Uani 1 1 d . . . . .
C15 C 0.9477(5) 0.67830(7) 0.5070(3) 0.0311(7) Uani 1 1 d . . . . .
H15 H 1.0596 0.6800 0.4551 0.037 Uiso 1 1 calc R U . . .
C16 C 0.9568(6) 0.69677(8) 0.6172(3) 0.0396(8) Uani 1 1 d . . . . .
H16 H 1.0726 0.7117 0.6396 0.048 Uiso 1 1 calc R U . . .
C17 C 0.7990(6) 0.69379(8) 0.6960(3) 0.0432(9) Uani 1 1 d . . . . .
H17 H 0.8070 0.7066 0.7725 0.052 Uiso 1 1 calc R U . . .
C18 C 0.6291(5) 0.67215(8) 0.6632(3) 0.0344(8) Uani 1 1 d . . . . .
H18 H 0.5223 0.6697 0.7183 0.041 Uiso 1 1 calc R U . . .
C19 C 0.5400(4) 0.59046(7) 0.4701(3) 0.0248(6) Uani 1 1 d . . . . .
H19 H 0.4385 0.5717 0.4455 0.030 Uiso 1 1 calc R U . . .
C20 C 0.7268(4) 0.57859(7) 0.5716(3) 0.0235(6) Uani 1 1 d . . . . .
H20 H 0.7733 0.5976 0.6302 0.028 Uiso 1 1 calc R U . . .
C21 C 0.8766(5) 0.57678(7) 0.4654(3) 0.0250(6) Uani 1 1 d . . . . .
H21 H 1.0081 0.5908 0.4855 0.030 Uiso 1 1 calc R U . . .
C22 C 0.6999(5) 0.59413(7) 0.3704(3) 0.0256(6) Uani 1 1 d . . . . .
H22 H 0.6561 0.5798 0.2938 0.031 Uiso 1 1 calc R U . . .
C23 C 0.6845(4) 0.54872(7) 0.6514(3) 0.0239(6) Uani 1 1 d . . . . .
C24 C 0.9254(5) 0.54247(7) 0.4228(3) 0.0261(7) Uani 1 1 d . . . . .
O1W O 0.3282(4) 0.51693(5) 1.1513(2) 0.0367(6) Uani 1 1 d . . . . .
H1A H 0.2850(13) 0.5038(4) 1.2089(17) 0.055 Uiso 1 1 d R U . . .
H1B H 0.462(4) 0.51634(6) 1.1533(2) 0.055 Uiso 1 1 d R U . . .
O2W O 0.2428(4) 0.49263(6) 0.9002(2) 0.0423(6) Uani 1 1 d . . . . .
H2A H 0.1888(18) 0.4741(6) 0.9054(3) 0.064 Uiso 1 1 d R U . . .
H2B H 0.2534(5) 0.4993(2) 0.977(3) 0.064 Uiso 1 1 d R U . . .
Na1 Na 0.18650(18) 0.52973(3) 0.72718(12) 0.0313(3) Uani 1 1 d . . . . .


_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 1.762(3) . ?
S1 C7 1.802(3) . ?
S2 C2 1.763(3) . ?
S2 C10 1.798(3) . ?
O1 C11 1.204(4) . ?
O2 C11 1.326(4) . ?
O2 H2 0.88(4) . ?
O3 C12 1.219(4) . ?
O3 Na1 2.406(2) . ?
O4 C12 1.319(4) . ?
O4 H4A 0.98(4) . ?
C1 C6 1.394(4) . ?
C1 C2 1.406(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C10 1.547(4) . ?
C7 C8 1.567(4) . ?
C7 H7 1.0000 . ?
C8 C11 1.507(4) . ?
C8 C9 1.564(4) . ?
C8 H8 1.0000 . ?
C9 C12 1.499(4) . ?
C9 C10 1.544(4) . ?
C9 H9 1.0000 . ?
C10 H10 1.0000 . ?
S3 C13 1.766(3) . ?
S3 C19 1.804(3) . ?
S4 C14 1.766(3) . ?
S4 C22 1.796(3) . ?
O5 C23 1.261(3) . ?
O5 Na1 2.296(2) . ?
O6 C23 1.259(3) . ?
O6 Na1 2.369(2) 1_655 ?
O7 C24 1.208(4) . ?
O7 Na1 2.380(2) 3_666 ?
O8 C24 1.337(4) . ?
O8 Na1 2.862(3) 1_655 ?
O8 H8A 0.92(4) . ?
C13 C18 1.387(5) . ?
C13 C14 1.403(4) . ?
C14 C15 1.391(4) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.554(4) . ?
C19 C22 1.555(4) . ?
C19 H19 1.0000 . ?
C20 C23 1.507(4) . ?
C20 C21 1.559(4) . ?
C20 H20 1.0000 . ?
C21 C24 1.492(4) . ?
C21 C22 1.557(4) . ?
C21 H21 1.0000 . ?
C22 H22 1.0000 . ?
O1W H1A 0.87(3) . ?
O1W H1B 0.84(2) . ?
O2W Na1 2.342(3) . ?
O2W H2A 0.82(3) . ?
O2W H2B 0.85(3) . ?
Na1 O6 2.369(2) 1_455 ?
Na1 O7 2.380(2) 3_666 ?
Na1 O8 2.862(3) 1_455 ?

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 C7 106.10(14) . . ?
C2 S2 C10 101.72(14) . . ?
C11 O2 H2 115.5 . . ?
C12 O3 Na1 129.5(2) . . ?
C12 O4 H4A 106.1 . . ?
C6 C1 C2 119.2(3) . . ?
C6 C1 S1 117.1(2) . . ?
C2 C1 S1 123.4(2) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 S2 119.3(2) . . ?
C1 C2 S2 121.1(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C10 C7 C8 89.2(2) . . ?
C10 C7 S1 116.9(2) . . ?
C8 C7 S1 117.5(2) . . ?
C10 C7 H7 110.5 . . ?
C8 C7 H7 110.5 . . ?
S1 C7 H7 110.5 . . ?
C11 C8 C9 114.4(2) . . ?
C11 C8 C7 111.5(3) . . ?
C9 C8 C7 88.5(2) . . ?
C11 C8 H8 113.4 . . ?
C9 C8 H8 113.4 . . ?
C7 C8 H8 113.4 . . ?
C12 C9 C10 118.9(2) . . ?
C12 C9 C8 117.9(2) . . ?
C10 C9 C8 89.5(2) . . ?
C12 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
C9 C10 C7 89.9(2) . . ?
C9 C10 S2 120.3(2) . . ?
C7 C10 S2 119.7(2) . . ?
C9 C10 H10 108.4 . . ?
C7 C10 H10 108.4 . . ?
S2 C10 H10 108.4 . . ?
O1 C11 O2 123.9(3) . . ?
O1 C11 C8 124.8(3) . . ?
O2 C11 C8 111.3(3) . . ?
O3 C12 O4 123.3(3) . . ?
O3 C12 C9 123.6(3) . . ?
O4 C12 C9 113.1(3) . . ?
C13 S3 C19 98.59(14) . . ?
C14 S4 C22 101.22(14) . . ?
C23 O5 Na1 146.9(2) . . ?
C23 O6 Na1 124.01(19) . 1_655 ?
C24 O7 Na1 133.4(2) . 3_666 ?
C24 O8 Na1 103.90(17) . 1_655 ?
C24 O8 H8A 108.6 . . ?
Na1 O8 H8A 107.9 1_655 . ?
C18 C13 C14 119.7(3) . . ?
C18 C13 S3 120.1(2) . . ?
C14 C13 S3 120.2(2) . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 S4 119.4(2) . . ?
C13 C14 S4 121.3(2) . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C20 C19 C22 89.7(2) . . ?
C20 C19 S3 117.6(2) . . ?
C22 C19 S3 117.3(2) . . ?
C20 C19 H19 110.2 . . ?
C22 C19 H19 110.2 . . ?
S3 C19 H19 110.2 . . ?
C23 C20 C19 116.9(2) . . ?
C23 C20 C21 122.1(2) . . ?
C19 C20 C21 89.7(2) . . ?
C23 C20 H20 108.8 . . ?
C19 C20 H20 108.8 . . ?
C21 C20 H20 108.8 . . ?
C24 C21 C22 112.2(3) . . ?
C24 C21 C20 115.3(2) . . ?
C22 C21 C20 89.5(2) . . ?
C24 C21 H21 112.6 . . ?
C22 C21 H21 112.6 . . ?
C20 C21 H21 112.6 . . ?
C19 C22 C21 89.8(2) . . ?
C19 C22 S4 116.8(2) . . ?
C21 C22 S4 116.0(2) . . ?
C19 C22 H22 110.9 . . ?
C21 C22 H22 110.9 . . ?
S4 C22 H22 110.9 . . ?
O6 C23 O5 123.6(3) . . ?
O6 C23 C20 119.9(2) . . ?
O5 C23 C20 116.4(3) . . ?
O7 C24 O8 123.4(3) . . ?
O7 C24 C21 123.9(3) . . ?
O8 C24 C21 112.8(3) . . ?
H1A O1W H1B 111.7 . . ?
Na1 O2W H2A 127.3 . . ?
Na1 O2W H2B 121.9 . . ?
H2A O2W H2B 101.6 . . ?
O5 Na1 O2W 104.30(9) . . ?
O5 Na1 O6 153.32(9) . 1_455 ?
O2W Na1 O6 102.33(9) . 1_455 ?
O5 Na1 O7 100.92(8) . 3_666 ?
O2W Na1 O7 74.72(9) . 3_666 ?
O6 Na1 O7 84.55(8) 1_455 3_666 ?
O5 Na1 O3 85.13(8) . . ?
O2W Na1 O3 107.01(10) . . ?
O6 Na1 O3 88.64(8) 1_455 . ?
O7 Na1 O3 173.19(9) 3_666 . ?
O5 Na1 O8 83.20(8) . 1_455 ?
O2W Na1 O8 143.97(9) . 1_455 ?
O6 Na1 O8 74.30(7) 1_455 1_455 ?
O7 Na1 O8 69.25(8) 3_666 1_455 ?
O3 Na1 O8 108.74(9) . 1_455 ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.066

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535555'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 O8 S2'
_chemical_formula_sum            'C24 H26 O8 S2'
_chemical_formula_weight         506.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.865(6)
_cell_length_b                   20.080(4)
_cell_length_c                   10.665(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.607(18)
_cell_angle_gamma                90
_cell_volume                     4886.8(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6033
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      52.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             2128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.381
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            29958
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         54.732
_diffrn_reflns_theta_full        54.732
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.901
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.901
_reflns_number_total             5475
_reflns_number_gt                4050
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Despite all our efforts, we were not able to isolate a crystal 
with a better signal to noise ratio. This low diffusing power 
explains the low resolution of the structure.
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1080P)²+16.7928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5475
_refine_ls_number_parameters     714
_refine_ls_number_restraints     455
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0833
_refine_ls_wR_factor_ref         0.2375
_refine_ls_wR_factor_gt          0.2177
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36046(8) 0.47840(8) 0.38551(16) 0.0457(5) Uani 1 1 d . . . . .
S2 S 0.35646(8) 0.31018(8) 0.35570(15) 0.0450(5) Uani 1 1 d . . . . .
O1 O 0.3074(2) 0.5106(3) 0.4192(5) 0.0608(14) Uani 1 1 d . . . . .
O2 O 0.4111(2) 0.5188(2) 0.3651(5) 0.0616(14) Uani 1 1 d . . . . .
O3 O 0.3050(2) 0.3044(2) 0.4278(4) 0.0507(13) Uani 1 1 d . . . . .
O4 O 0.3813(2) 0.2504(2) 0.3080(4) 0.0546(13) Uani 1 1 d . . . . .
O5 O 0.4837(2) 0.3783(3) 1.1807(5) 0.0623(14) Uani 1 1 d . . . . .
O6 O 0.5819(2) 0.3874(2) 1.1828(4) 0.0546(13) Uani 1 1 d . . . . .
O7 O 0.6619(2) 0.3694(2) 0.9454(5) 0.0560(13) Uani 1 1 d . . . . .
O8 O 0.6402(2) 0.2731(2) 1.0395(4) 0.0504(13) Uani 1 1 d . . . . .
C1 C 0.3430(3) 0.4344(3) 0.2416(6) 0.0392(17) Uani 1 1 d . . . . .
C2 C 0.3405(3) 0.3661(3) 0.2281(6) 0.0383(16) Uani 1 1 d . . . . .
C3 C 0.3276(3) 0.3388(4) 0.1108(6) 0.0497(19) Uani 1 1 d . . . . .
H3 H 0.3269 0.2917 0.1009 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3158(3) 0.3792(4) 0.0082(7) 0.056(2) Uani 1 1 d . . . . .
H4 H 0.3055 0.3600 -0.0716 0.068 Uiso 1 1 calc R U . . .
C5 C 0.3188(3) 0.4478(4) 0.0206(7) 0.056(2) Uani 1 1 d . . . . .
H5 H 0.3115 0.4757 -0.0504 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3326(3) 0.4750(4) 0.1379(7) 0.0512(19) Uani 1 1 d . . . . .
H6 H 0.3350 0.5220 0.1472 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3811(3) 0.4177(3) 0.5060(6) 0.0419(17) Uani 1 1 d . . . . .
H7 H 0.3450 0.4026 0.5462 0.050 Uiso 1 1 calc R U . . .
C8 C 0.4213(3) 0.4494(3) 0.6031(6) 0.0453(18) Uani 1 1 d . . . . .
H8 H 0.4514 0.4781 0.5776 0.054 Uiso 1 1 calc R U . . .
C9 C 0.4162(3) 0.4383(3) 0.7266(6) 0.0463(18) Uani 1 1 d . . . . .
H9 H 0.3793 0.4254 0.7551 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4663(3) 0.4458(3) 0.8172(6) 0.0465(18) Uani 1 1 d . . . . .
H11 H 0.4947 0.4790 0.8025 0.056 Uiso 1 1 calc R U . . .
C12 C 0.4738(3) 0.4078(3) 0.9202(6) 0.0431(17) Uani 1 1 d . . . . .
H12 H 0.4404 0.3879 0.9531 0.052 Uiso 1 1 calc R U . . .
C14 C 0.5318(3) 0.3956(3) 0.9847(6) 0.0401(16) Uani 1 1 d . . . . .
H14 H 0.5575 0.4347 0.9699 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5283(4) 0.3868(3) 1.1261(7) 0.0459(18) Uani 1 1 d . . . . .
C16 C 0.5858(4) 0.3746(4) 1.3178(6) 0.058(2) Uani 1 1 d . . . . .
H16A H 0.5702 0.3299 1.3359 0.069 Uiso 1 1 calc R U . . .
H16B H 0.5633 0.4083 1.3624 0.069 Uiso 1 1 calc R U . . .
C17 C 0.6496(4) 0.3788(5) 1.3584(8) 0.084(3) Uani 1 1 d . . . . .
H17A H 0.6702 0.3406 1.3247 0.127 Uiso 1 1 calc R U . . .
H17B H 0.6544 0.3783 1.4503 0.127 Uiso 1 1 calc R U . . .
H17C H 0.6660 0.4201 1.3266 0.127 Uiso 1 1 calc R U . . .
C18 C 0.4113(3) 0.3553(3) 0.4477(6) 0.0423(17) Uani 1 1 d . . . . .
H18 H 0.4424 0.3707 0.3925 0.051 Uiso 1 1 calc R U . . .
C19 C 0.4382(3) 0.3127(3) 0.5504(6) 0.0444(18) Uani 1 1 d . . . . .
H19 H 0.4148 0.2792 0.5852 0.053 Uiso 1 1 calc R U . . .
C20 C 0.4935(4) 0.3195(3) 0.5956(6) 0.0464(18) Uani 1 1 d . . . . .
H20 H 0.5212 0.3385 0.5432 0.056 Uiso 1 1 calc R U . . .
C21 C 0.5131(3) 0.2991(3) 0.7214(6) 0.0457(18) Uani 1 1 d . . . . .
H21 H 0.4955 0.2614 0.7573 0.055 Uiso 1 1 calc R U . . .
C22 C 0.5552(3) 0.3316(3) 0.7885(6) 0.0434(17) Uani 1 1 d . . . . .
H22 H 0.5827 0.3566 0.7447 0.052 Uiso 1 1 calc R U . . .
C23 C 0.5614(3) 0.3308(3) 0.9299(6) 0.0428(17) Uani 1 1 d . . . . .
H23 H 0.5415 0.2903 0.9613 0.051 Uiso 1 1 calc R U . . .
C24 C 0.6258(3) 0.3283(4) 0.9723(6) 0.0465(18) Uani 1 1 d . . . . .
C25 C 0.7019(3) 0.2670(4) 1.0784(7) 0.058(2) Uani 1 1 d . . . . .
H25A H 0.7170 0.3096 1.1142 0.070 Uiso 1 1 calc R U . . .
H25B H 0.7247 0.2554 1.0057 0.070 Uiso 1 1 calc R U . . .
C26 C 0.7074(4) 0.2124(4) 1.1767(8) 0.073(2) Uani 1 1 d . . . . .
H26A H 0.6837 0.2240 1.2471 0.110 Uiso 1 1 calc R U . . .
H26B H 0.7485 0.2078 1.2071 0.110 Uiso 1 1 calc R U . . .
H26C H 0.6934 0.1703 1.1394 0.110 Uiso 1 1 calc R U . . .
S3 S 0.20488(11) 0.40955(11) 0.6891(2) 0.0706(7) Uani 1 1 d . . . . .
S4 S 0.12702(17) 0.39801(16) 0.4045(3) 0.1143(11) Uani 1 1 d . . . . .
C27 C 0.1794(16) 0.336(2) 0.598(3) 0.065(6) Uani 0.5 1 d . U P A 1
C28 C 0.1418(11) 0.3365(12) 0.479(2) 0.070(6) Uani 0.5 1 d . U P A 1
C29 C 0.1220(10) 0.2731(9) 0.430(2) 0.070(5) Uani 0.5 1 d . U P A 1
H29 H 0.0957 0.2704 0.3579 0.085 Uiso 0.5 1 calc R U P A 1
C30 C 0.1438(10) 0.2124(12) 0.496(2) 0.069(5) Uani 0.5 1 d . U P A 1
H30 H 0.1328 0.1703 0.4615 0.082 Uiso 0.5 1 calc R U P A 1
C31 C 0.1791(12) 0.2147(13) 0.603(2) 0.073(6) Uani 0.5 1 d . U P A 1
H31 H 0.1917 0.1744 0.6430 0.088 Uiso 0.5 1 calc R U P A 1
C32 C 0.1971(12) 0.2757(14) 0.655(2) 0.072(5) Uani 0.5 1 d . U P A 1
H32 H 0.2216 0.2764 0.7305 0.087 Uiso 0.5 1 calc R U P A 1
C27B C 0.1910(17) 0.331(2) 0.627(3) 0.070(6) Uani 0.5 1 d . U P A 2
C28B C 0.1580(13) 0.3219(13) 0.519(3) 0.074(5) Uani 0.5 1 d . U P A 2
C29B C 0.1470(12) 0.2555(15) 0.477(2) 0.083(5) Uani 0.5 1 d . U P A 2
H29B H 0.1260 0.2466 0.3990 0.100 Uiso 0.5 1 calc R U P A 2
C30B C 0.1679(13) 0.2057(14) 0.552(3) 0.082(6) Uani 0.5 1 d . U P A 2
H30B H 0.1601 0.1613 0.5259 0.098 Uiso 0.5 1 calc R U P A 2
C31B C 0.2000(10) 0.2153(11) 0.666(2) 0.079(5) Uani 0.5 1 d . U P A 2
H31B H 0.2128 0.1780 0.7153 0.095 Uiso 0.5 1 calc R U P A 2
C32B C 0.2130(13) 0.2778(14) 0.706(2) 0.075(5) Uani 0.5 1 d . U P A 2
H32B H 0.2356 0.2860 0.7823 0.090 Uiso 0.5 1 calc R U P A 2
C33 C 0.1832(4) 0.4749(4) 0.5827(8) 0.063(2) Uani 1 1 d . . . . .
H33 H 0.2119 0.4775 0.5159 0.075 Uiso 1 1 calc R U . . .
C34 C 0.1837(4) 0.5397(4) 0.6523(8) 0.065(2) Uani 1 1 d . . . . .
H34 H 0.1730 0.5398 0.7369 0.078 Uiso 1 1 calc R U . . .
C35 C 0.1985(3) 0.5967(4) 0.6014(9) 0.065(2) Uani 1 1 d . . . . .
H35 H 0.2244 0.5960 0.5351 0.078 Uiso 1 1 calc R U . . .
C36 C 0.1762(4) 0.6615(5) 0.6435(10) 0.076(3) Uani 1 1 d . . . . .
H36 H 0.1697 0.6678 0.7298 0.091 Uiso 1 1 calc R U . . .
C37 C 0.1652(4) 0.7109(5) 0.5639(12) 0.090(3) Uani 1 1 d . . . . .
H37 H 0.1845 0.7108 0.4876 0.108 Uiso 1 1 calc R U . . .
C38 C 0.1246(6) 0.7663(7) 0.5860(13) 0.120(4) Uiso 1 1 d . . . . .
H38A H 0.1087 0.7654 0.6711 0.144 Uiso 0.6 1 calc R U P B 1
H38B H 0.1256 0.7681 0.6798 0.144 Uiso 0.4 1 calc R U P C 2
C39 C 0.1529(6) 0.8354(6) 0.5522(15) 0.100(4) Uani 1 1 d . . . . .
C40 C 0.1970(5) 0.9310(6) 0.6196(14) 0.120(4) Uani 1 1 d . . . . .
H40A H 0.2191 0.9464 0.6970 0.144 Uiso 1 1 calc R U . . .
H40B H 0.2258 0.9208 0.5568 0.144 Uiso 1 1 calc R U . . .
C41 C 0.1600(6) 0.9838(6) 0.5724(12) 0.115(4) Uani 1 1 d . . . . .
H41A H 0.1455 0.9737 0.4861 0.173 Uiso 1 1 calc R U . . .
H41B H 0.1823 1.0255 0.5735 0.173 Uiso 1 1 calc R U . . .
H41C H 0.1267 0.9886 0.6254 0.173 Uiso 1 1 calc R U . . .
C42 C 0.1212(4) 0.4631(5) 0.5197(9) 0.080(3) Uani 1 1 d . . . . .
H42 H 0.0937 0.4493 0.5841 0.096 Uiso 1 1 calc R U . . .
C43 C 0.0979(5) 0.5241(6) 0.4503(11) 0.108(4) Uani 1 1 d . . . . .
H43 H 0.1107 0.5318 0.3685 0.129 Uiso 1 1 calc R U . . .
C44 C 0.0615(6) 0.5671(7) 0.4941(13) 0.124(4) Uiso 1 1 d . . . . .
H44A H 0.0364 0.5591 0.5603 0.148 Uiso 0.6 1 calc R U P D 1
H44B H 0.0342 0.5461 0.5450 0.148 Uiso 0.4 1 calc R U P E 2
C45 C 0.0656(10) 0.6337(11) 0.420(2) 0.064(6) Uiso 0.4 1 d . . P F 1
H45 H 0.0779 0.6374 0.3373 0.077 Uiso 0.4 1 calc R U P F 1
C46 C 0.0478(10) 0.6903(13) 0.498(2) 0.067(6) Uiso 0.4 1 d . . P F 1
H46 H 0.0217 0.6850 0.5631 0.080 Uiso 0.4 1 calc R U P F 1
C47 C 0.0731(11) 0.7558(13) 0.468(2) 0.088(7) Uani 0.4 1 d D U P F 1
H47 H 0.0889 0.7578 0.3825 0.105 Uiso 0.4 1 calc R U P F 1
C45B C 0.0509(9) 0.6418(11) 0.486(2) 0.099(6) Uiso 0.6 1 d . . P F 2
H45B H 0.0503 0.6619 0.4049 0.119 Uiso 0.6 1 calc R U P F 2
C46B C 0.0425(10) 0.6806(12) 0.583(3) 0.128(8) Uiso 0.6 1 d . . P F 2
H46B H 0.0281 0.6662 0.6600 0.154 Uiso 0.6 1 calc R U P F 2
C47B C 0.0605(9) 0.7567(12) 0.551(3) 0.132(6) Uani 0.6 1 d D U P F 2
H47B H 0.0535 0.7640 0.4587 0.158 Uiso 0.6 1 calc R U P F 2
C48B C 0.0204(16) 0.8018(15) 0.618(3) 0.164(8) Uani 0.6 1 d D U P F 2
O15B O -0.0101(12) 0.7940(12) 0.713(3) 0.236(10) Uani 0.6 1 d . U P F 2
O16B O 0.0120(13) 0.8530(13) 0.541(3) 0.177(7) Uani 0.6 1 d D U P F 2
C49B C -0.0320(14) 0.8999(17) 0.577(4) 0.181(9) Uani 0.6 1 d . U P F 2
H49A H -0.0459 0.9256 0.5016 0.217 Uiso 0.6 1 calc R U P F 2
H49B H -0.0658 0.8745 0.6054 0.217 Uiso 0.6 1 calc R U P F 2
C50B C -0.0145(11) 0.9419(18) 0.666(3) 0.181(12) Uani 0.6 1 d . U P F 2
H50A H -0.0110 0.9187 0.7466 0.272 Uiso 0.6 1 calc R U P F 2
H50B H -0.0432 0.9781 0.6695 0.272 Uiso 0.6 1 calc R U P F 2
H50C H 0.0236 0.9605 0.6471 0.272 Uiso 0.6 1 calc R U P F 2
C48A C 0.0244(15) 0.8133(19) 0.492(3) 0.133(7) Uani 0.4 1 d D U P F 1
O15A O 0.0181(16) 0.8382(18) 0.595(2) 0.151(9) Uani 0.4 1 d D U P F 1
O16A O 0.0051(13) 0.8397(15) 0.392(2) 0.179(8) Uani 0.4 1 d D U P F 1
C49A C -0.021(2) 0.908(2) 0.412(4) 0.180(10) Uani 0.4 1 d . U P F 1
H49C H -0.0194 0.9176 0.5033 0.216 Uiso 0.4 1 calc R U P F 1
H49D H -0.0630 0.9070 0.3816 0.216 Uiso 0.4 1 calc R U P F 1
C50A C 0.013(2) 0.968(2) 0.338(4) 0.191(13) Uani 0.4 1 d . U P F 1
H50D H 0.0439 0.9866 0.3954 0.286 Uiso 0.4 1 calc R U P F 1
H50E H -0.0152 1.0024 0.3121 0.286 Uiso 0.4 1 calc R U P F 1
H50F H 0.0304 0.9489 0.2645 0.286 Uiso 0.4 1 calc R U P F 1
O9 O 0.2673(3) 0.4109(3) 0.7078(6) 0.0847(19) Uani 1 1 d . . . . .
O10 O 0.1695(3) 0.4147(3) 0.7946(6) 0.094(2) Uani 1 1 d . . . . .
O11 O 0.1743(4) 0.4146(4) 0.3229(7) 0.126(3) Uani 1 1 d . . . . .
O12 O 0.0703(5) 0.3842(5) 0.3497(10) 0.175(4) Uani 1 1 d . . . . .
O13 O 0.1597(6) 0.8478(5) 0.4438(11) 0.162(4) Uani 1 1 d . . . . .
O14 O 0.1661(3) 0.8704(4) 0.6476(9) 0.106(2) Uani 1 1 d . . . . .


_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 O1 1.440(5) . ?
S1 O2 1.442(5) . ?
S1 C1 1.793(6) . ?
S1 C7 1.812(7) . ?
S2 O4 1.435(5) . ?
S2 O3 1.451(5) . ?
S2 C2 1.783(7) . ?
S2 C18 1.789(7) . ?
O5 C15 1.218(8) . ?
O6 C15 1.332(9) . ?
O6 C16 1.460(8) . ?
O7 C24 1.215(8) . ?
O8 C24 1.348(8) . ?
O8 C25 1.451(9) . ?
C1 C2 1.381(9) . ?
C1 C6 1.382(9) . ?
C2 C3 1.381(9) . ?
C3 C4 1.376(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.484(10) . ?
C7 C18 1.577(9) . ?
C7 H7 1.0000 . ?
C8 C9 1.348(9) . ?
C8 H8 0.9500 . ?
C9 C11 1.459(10) . ?
C9 H9 0.9500 . ?
C11 C12 1.339(9) . ?
C11 H11 0.9500 . ?
C12 C14 1.474(9) . ?
C12 H12 0.9500 . ?
C14 C15 1.525(10) . ?
C14 C23 1.595(9) . ?
C14 H14 1.0000 . ?
C16 C17 1.497(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.491(9) . ?
C18 H18 1.0000 . ?
C19 C20 1.333(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.447(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.332(10) . ?
C21 H21 0.9500 . ?
C22 C23 1.506(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.514(10) . ?
C23 H23 1.0000 . ?
C25 C26 1.516(11) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
S3 O9 1.428(7) . ?
S3 O10 1.431(6) . ?
S3 C27B 1.74(4) . ?
S3 C33 1.785(8) . ?
S3 C27 1.84(5) . ?
S4 O12 1.415(10) . ?
S4 O11 1.468(8) . ?
S4 C28 1.50(2) . ?
S4 C42 1.805(9) . ?
S4 C28B 2.05(2) . ?
C27 C32 1.41(4) . ?
C27 C28 1.48(4) . ?
C28 C29 1.44(3) . ?
C29 C30 1.47(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.36(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.40(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C27B C28B 1.35(4) . ?
C27B C32B 1.43(4) . ?
C28B C29B 1.42(3) . ?
C29B C30B 1.35(4) . ?
C29B H29B 0.9500 . ?
C30B C31B 1.39(3) . ?
C30B H30B 0.9500 . ?
C31B C32B 1.35(3) . ?
C31B H31B 0.9500 . ?
C32B H32B 0.9500 . ?
C33 C34 1.498(11) . ?
C33 C42 1.548(12) . ?
C33 H33 1.0000 . ?
C34 C35 1.319(11) . ?
C34 H34 0.9500 . ?
C35 C36 1.479(12) . ?
C35 H35 0.9500 . ?
C36 C37 1.319(13) . ?
C36 H36 0.9500 . ?
C37 C38 1.476(15) . ?
C37 H37 0.9500 . ?
C38 C47B 1.50(2) . ?
C38 C39 1.581(17) . ?
C38 C47 1.68(3) . ?
C38 H38A 1.0000 . ?
C38 H38B 1.0000 . ?
C39 O13 1.202(14) . ?
C39 O14 1.259(15) . ?
C40 C41 1.429(15) . ?
C40 O14 1.447(12) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.511(14) . ?
C42 H42 1.0000 . ?
C43 C44 1.306(16) . ?
C43 H43 0.9500 . ?
C44 C45B 1.52(3) . ?
C44 C45 1.56(3) . ?
C44 H44A 0.9500 . ?
C44 H44B 0.9500 . ?
C45 C46 1.48(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.48(4) . ?
C46 H46 0.9500 . ?
C47 C48A 1.63(3) . ?
C47 H47 1.0000 . ?
C45B C46B 1.32(3) . ?
C45B H45B 0.9500 . ?
C46B C47B 1.62(3) . ?
C46B H46B 0.9500 . ?
C47B C48B 1.503(19) . ?
C47B H47B 1.0000 . ?
C48B O15B 1.27(3) . ?
C48B O16B 1.327(19) . ?
O16B C49B 1.45(3) . ?
C49B C50B 1.31(4) . ?
C49B H49A 0.9900 . ?
C49B H49B 0.9900 . ?
C50B H50A 0.9800 . ?
C50B H50B 0.9800 . ?
C50B H50C 0.9800 . ?
C48A O15A 1.231(19) . ?
C48A O16A 1.24(3) . ?
O16A C49A 1.51(4) . ?
C49A C50A 1.66(6) . ?
C49A H49C 0.9900 . ?
C49A H49D 0.9900 . ?
C50A H50D 0.9800 . ?
C50A H50E 0.9800 . ?
C50A H50F 0.9800 . ?

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
O1 S1 O2 118.8(3) . . ?
O1 S1 C1 106.8(3) . . ?
O2 S1 C1 106.6(3) . . ?
O1 S1 C7 108.1(3) . . ?
O2 S1 C7 108.1(3) . . ?
C1 S1 C7 108.0(3) . . ?
O4 S2 O3 118.3(3) . . ?
O4 S2 C2 108.8(3) . . ?
O3 S2 C2 108.7(3) . . ?
O4 S2 C18 109.8(3) . . ?
O3 S2 C18 108.3(3) . . ?
C2 S2 C18 101.7(3) . . ?
C15 O6 C16 116.4(6) . . ?
C24 O8 C25 115.0(6) . . ?
C2 C1 C6 119.9(6) . . ?
C2 C1 S1 125.7(5) . . ?
C6 C1 S1 114.4(5) . . ?
C1 C2 C3 119.6(6) . . ?
C1 C2 S2 122.7(5) . . ?
C3 C2 S2 117.6(5) . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.3(7) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.2(7) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C1 C6 C5 120.6(7) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C18 110.3(6) . . ?
C8 C7 S1 109.2(4) . . ?
C18 C7 S1 110.8(4) . . ?
C8 C7 H7 108.8 . . ?
C18 C7 H7 108.8 . . ?
S1 C7 H7 108.8 . . ?
C9 C8 C7 121.5(7) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C11 121.1(7) . . ?
C8 C9 H9 119.4 . . ?
C11 C9 H9 119.4 . . ?
C12 C11 C9 122.7(7) . . ?
C12 C11 H11 118.7 . . ?
C9 C11 H11 118.7 . . ?
C11 C12 C14 122.9(7) . . ?
C11 C12 H12 118.5 . . ?
C14 C12 H12 118.5 . . ?
C12 C14 C15 112.3(6) . . ?
C12 C14 C23 110.8(5) . . ?
C15 C14 C23 108.5(5) . . ?
C12 C14 H14 108.4 . . ?
C15 C14 H14 108.4 . . ?
C23 C14 H14 108.4 . . ?
O5 C15 O6 124.0(6) . . ?
O5 C15 C14 125.9(7) . . ?
O6 C15 C14 110.1(6) . . ?
O6 C16 C17 105.9(7) . . ?
O6 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
O6 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C7 109.7(5) . . ?
C19 C18 S2 110.7(5) . . ?
C7 C18 S2 108.0(5) . . ?
C19 C18 H18 109.5 . . ?
C7 C18 H18 109.5 . . ?
S2 C18 H18 109.5 . . ?
C20 C19 C18 123.0(7) . . ?
C20 C19 H19 118.5 . . ?
C18 C19 H19 118.5 . . ?
C19 C20 C21 122.6(7) . . ?
C19 C20 H20 118.7 . . ?
C21 C20 H20 118.7 . . ?
C22 C21 C20 122.0(7) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 123.5(6) . . ?
C21 C22 H22 118.3 . . ?
C23 C22 H22 118.3 . . ?
C22 C23 C24 109.1(6) . . ?
C22 C23 C14 110.1(5) . . ?
C24 C23 C14 110.3(5) . . ?
C22 C23 H23 109.1 . . ?
C24 C23 H23 109.1 . . ?
C14 C23 H23 109.1 . . ?
O7 C24 O8 122.6(7) . . ?
O7 C24 C23 124.6(7) . . ?
O8 C24 C23 112.8(6) . . ?
O8 C25 C26 107.2(6) . . ?
O8 C25 H25A 110.3 . . ?
C26 C25 H25A 110.3 . . ?
O8 C25 H25B 110.3 . . ?
C26 C25 H25B 110.3 . . ?
H25A C25 H25B 108.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O9 S3 O10 119.9(4) . . ?
O9 S3 C27B 103.2(13) . . ?
O10 S3 C27B 105.4(14) . . ?
O9 S3 C33 108.0(4) . . ?
O10 S3 C33 107.4(4) . . ?
C27B S3 C33 113.1(11) . . ?
O9 S3 C27 111.7(11) . . ?
O10 S3 C27 107.3(13) . . ?
C33 S3 C27 100.7(9) . . ?
O12 S4 O11 119.2(7) . . ?
O12 S4 C28 103.2(11) . . ?
O11 S4 C28 110.7(11) . . ?
O12 S4 C42 108.6(6) . . ?
O11 S4 C42 109.1(5) . . ?
C28 S4 C42 105.0(11) . . ?
O12 S4 C28B 111.9(10) . . ?
O11 S4 C28B 106.4(9) . . ?
C42 S4 C28B 99.9(9) . . ?
C32 C27 C28 120(3) . . ?
C32 C27 S3 113(2) . . ?
C28 C27 S3 127(2) . . ?
C29 C28 C27 117(2) . . ?
C29 C28 S4 118.7(19) . . ?
C27 C28 S4 124(2) . . ?
C28 C29 C30 118(2) . . ?
C28 C29 H29 121.0 . . ?
C30 C29 H29 121.0 . . ?
C31 C30 C29 122(2) . . ?
C31 C30 H30 118.8 . . ?
C29 C30 H30 118.8 . . ?
C30 C31 C32 121(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C27 121(2) . . ?
C31 C32 H32 119.5 . . ?
C27 C32 H32 119.5 . . ?
C28B C27B C32B 124(3) . . ?
C28B C27B S3 122(3) . . ?
C32B C27B S3 114(2) . . ?
C27B C28B C29B 118(2) . . ?
C27B C28B S4 124(2) . . ?
C29B C28B S4 117(2) . . ?
C30B C29B C28B 117(2) . . ?
C30B C29B H29B 121.5 . . ?
C28B C29B H29B 121.5 . . ?
C29B C30B C31B 124(3) . . ?
C29B C30B H30B 117.8 . . ?
C31B C30B H30B 117.8 . . ?
C32B C31B C30B 120(2) . . ?
C32B C31B H31B 120.1 . . ?
C30B C31B H31B 120.1 . . ?
C31B C32B C27B 116(3) . . ?
C31B C32B H32B 121.8 . . ?
C27B C32B H32B 121.8 . . ?
C34 C33 C42 109.1(7) . . ?
C34 C33 S3 109.3(6) . . ?
C42 C33 S3 111.9(6) . . ?
C34 C33 H33 108.8 . . ?
C42 C33 H33 108.8 . . ?
S3 C33 H33 108.8 . . ?
C35 C34 C33 122.9(8) . . ?
C35 C34 H34 118.6 . . ?
C33 C34 H34 118.6 . . ?
C34 C35 C36 122.4(9) . . ?
C34 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C37 C36 C35 121.5(10) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C36 C37 C38 124.1(11) . . ?
C36 C37 H37 118.0 . . ?
C38 C37 H37 118.0 . . ?
C37 C38 C47B 118.5(13) . . ?
C37 C38 C39 110.8(10) . . ?
C47B C38 C39 117.6(14) . . ?
C37 C38 C47 101.7(11) . . ?
C39 C38 C47 102.5(13) . . ?
C37 C38 H38A 113.6 . . ?
C39 C38 H38A 113.6 . . ?
C47 C38 H38A 113.6 . . ?
C37 C38 H38B 102.2 . . ?
C47B C38 H38B 102.2 . . ?
C39 C38 H38B 102.2 . . ?
O13 C39 O14 128.5(13) . . ?
O13 C39 C38 118.8(14) . . ?
O14 C39 C38 112.8(12) . . ?
C41 C40 O14 114.3(10) . . ?
C41 C40 H40A 108.7 . . ?
O14 C40 H40A 108.7 . . ?
C41 C40 H40B 108.7 . . ?
O14 C40 H40B 108.7 . . ?
H40A C40 H40B 107.6 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C33 112.0(8) . . ?
C43 C42 S4 107.0(7) . . ?
C33 C42 S4 107.6(6) . . ?
C43 C42 H42 110.1 . . ?
C33 C42 H42 110.1 . . ?
S4 C42 H42 110.1 . . ?
C44 C43 C42 125.0(13) . . ?
C44 C43 H43 117.5 . . ?
C42 C43 H43 117.5 . . ?
C43 C44 C45B 137.1(15) . . ?
C43 C44 C45 109.1(15) . . ?
C43 C44 H44A 125.5 . . ?
C45 C44 H44A 125.5 . . ?
C43 C44 H44B 111.4 . . ?
C45B C44 H44B 111.4 . . ?
C46 C45 C44 111(2) . . ?
C46 C45 H45 124.7 . . ?
C44 C45 H45 124.7 . . ?
C45 C46 C47 116(2) . . ?
C45 C46 H46 122.1 . . ?
C47 C46 H46 122.1 . . ?
C46 C47 C48A 108(2) . . ?
C46 C47 C38 102.3(17) . . ?
C48A C47 C38 104.3(19) . . ?
C46 C47 H47 113.7 . . ?
C48A C47 H47 113.7 . . ?
C38 C47 H47 113.7 . . ?
C46B C45B C44 124(2) . . ?
C46B C45B H45B 117.8 . . ?
C44 C45B H45B 117.8 . . ?
C45B C46B C47B 110(2) . . ?
C45B C46B H46B 125.1 . . ?
C47B C46B H46B 125.1 . . ?
C48B C47B C38 115(2) . . ?
C48B C47B C46B 107(2) . . ?
C38 C47B C46B 109.0(18) . . ?
C48B C47B H47B 108.5 . . ?
C38 C47B H47B 108.5 . . ?
C46B C47B H47B 108.5 . . ?
O15B C48B O16B 122(3) . . ?
O15B C48B C47B 133(3) . . ?
O16B C48B C47B 104(2) . . ?
C48B O16B C49B 114(3) . . ?
C50B C49B O16B 115(3) . . ?
C50B C49B H49A 108.5 . . ?
O16B C49B H49A 108.5 . . ?
C50B C49B H49B 108.5 . . ?
O16B C49B H49B 108.5 . . ?
H49A C49B H49B 107.5 . . ?
C49B C50B H50A 109.5 . . ?
C49B C50B H50B 109.5 . . ?
H50A C50B H50B 109.5 . . ?
C49B C50B H50C 109.5 . . ?
H50A C50B H50C 109.5 . . ?
H50B C50B H50C 109.5 . . ?
O15A C48A O16A 123(3) . . ?
O15A C48A C47 123(3) . . ?
O16A C48A C47 112(2) . . ?
C48A O16A C49A 113(3) . . ?
O16A C49A C50A 113(3) . . ?
O16A C49A H49C 109.1 . . ?
C50A C49A H49C 109.1 . . ?
O16A C49A H49D 109.1 . . ?
C50A C49A H49D 109.1 . . ?
H49C C49A H49D 107.8 . . ?
C49A C50A H50D 109.5 . . ?
C49A C50A H50E 109.5 . . ?
H50D C50A H50E 109.5 . . ?
C49A C50A H50F 109.5 . . ?
H50D C50A H50F 109.5 . . ?
H50E C50A H50F 109.5 . . ?
C39 O14 C40 113.5(11) . . ?

_refine_diff_density_max         0.772
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.078

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535549'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20  H22  O4  S2'
_chemical_formula_sum            'C20 H22 O4 S2'
_chemical_formula_weight         390.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.9549(2)
_cell_length_b                   15.3259(4)
_cell_length_c                   21.7847(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.458(2)
_cell_angle_gamma                90
_cell_volume                     1984.54(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5835
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      67.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.614
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            17607
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.528
_diffrn_reflns_theta_max         67.755
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3572
_reflns_number_gt                3001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
As a G-type alert appeared in checkcif procedure, we carefully examined the 
symmetry of the crystal structure. An ADDSYM procedure with Platon did not 
indicated any supplementary symmetry except for high values of tolerance. 
A C-centered monoclinic unit cell could be found and the refinement was quite 
good in that case. However, the latter unit cell did not indexed all 
diffraction pattern and the final R factors and ADPs were a little bit worse. 
All these facts strengthened us in the use of the P-monoclic symmetry. 
 
Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.4821P] where P=(Fo²+2Fc²)/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_extinction_coef       .
_refine_ls_number_reflns         3572
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51404(7) 0.62314(3) 0.03672(2) 0.04374(14) Uani 1 1 d . . . . .
S2 S 0.93375(7) 0.60830(3) -0.03925(2) 0.03973(13) Uani 1 1 d . . . . .
O1 O -0.0437(2) 0.70655(8) 0.29313(5) 0.0471(3) Uani 1 1 d . . . . .
O2 O -0.34059(19) 0.61831(7) 0.27606(5) 0.0404(3) Uani 1 1 d . . . . .
O3 O 1.53595(19) 0.68724(8) -0.28755(5) 0.0462(3) Uani 1 1 d . . . . .
O4 O 1.82245(19) 0.59371(7) -0.27055(5) 0.0397(3) Uani 1 1 d . . . . .
C1 C 0.6540(3) 0.72018(10) 0.01730(7) 0.0370(4) Uani 1 1 d . . . . .
C2 C 0.8451(3) 0.71326(10) -0.01682(7) 0.0365(4) Uani 1 1 d . . . . .
C3 C 0.9625(3) 0.78804(12) -0.03108(8) 0.0503(5) Uani 1 1 d . . . . .
H3 H 1.0952 0.7833 -0.0530 0.060 Uiso 1 1 calc R U . . .
C4 C 0.8885(4) 0.86910(13) -0.01386(9) 0.0652(6) Uani 1 1 d . . . . .
H4 H 0.9699 0.9199 -0.0239 0.078 Uiso 1 1 calc R U . . .
C5 C 0.6959(4) 0.87632(12) 0.01797(9) 0.0642(6) Uani 1 1 d . . . . .
H5 H 0.6433 0.9323 0.0292 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5794(3) 0.80240(12) 0.03355(8) 0.0505(4) Uani 1 1 d . . . . .
H6 H 0.4471 0.8078 0.0556 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3976(3) 0.65372(11) 0.10509(7) 0.0387(4) Uani 1 1 d . . . . .
H7 H 0.4732 0.6966 0.1301 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2072(3) 0.61973(10) 0.12387(7) 0.0376(4) Uani 1 1 d . . . . .
H8 H 0.1258 0.5788 0.0985 0.045 Uiso 1 1 calc R U . . .
C9 C 0.1232(3) 0.64425(10) 0.18219(7) 0.0350(3) Uani 1 1 d . . . . .
H9 H 0.2141 0.6824 0.2075 0.042 Uiso 1 1 calc R U . . .
C10 C -0.0703(3) 0.61813(10) 0.20361(7) 0.0369(4) Uani 1 1 d . . . . .
H10 H -0.1609 0.5767 0.1811 0.044 Uiso 1 1 calc R U . . .
C11 C -0.1447(3) 0.65292(10) 0.26182(7) 0.0344(3) Uani 1 1 d . . . . .
C12 C -0.4317(4) 0.64973(13) 0.33225(9) 0.0561(5) Uani 1 1 d . . . . .
H12A H -0.5083 0.7064 0.3246 0.067 Uiso 1 1 calc R U . . .
H12B H -0.3088 0.6583 0.3643 0.067 Uiso 1 1 calc R U . . .
C13 C -0.5932(3) 0.58477(13) 0.35302(9) 0.0557(5) Uani 1 1 d . . . . .
H13A H -0.7083 0.5735 0.3199 0.084 Uiso 1 1 calc R U . . .
H13B H -0.6650 0.6072 0.3891 0.084 Uiso 1 1 calc R U . . .
H13C H -0.5137 0.5304 0.3639 0.084 Uiso 1 1 calc R U . . .
C14 C 1.0681(3) 0.63515(11) -0.10594(7) 0.0370(4) Uani 1 1 d . . . . .
H14 H 1.0039 0.6800 -0.1314 0.044 Uiso 1 1 calc R U . . .
C15 C 1.2549(3) 0.59667(10) -0.12328(7) 0.0367(3) Uani 1 1 d . . . . .
H15 H 1.3253 0.5525 -0.0983 0.044 Uiso 1 1 calc R U . . .
C16 C 1.3503(3) 0.62196(10) -0.17995(7) 0.0347(3) Uani 1 1 d . . . . .
H16 H 1.2679 0.6632 -0.2049 0.042 Uiso 1 1 calc R U . . .
C17 C 1.5427(3) 0.59318(10) -0.20074(7) 0.0366(4) Uani 1 1 d . . . . .
H17 H 1.6252 0.5485 -0.1792 0.044 Uiso 1 1 calc R U . . .
C18 C 1.6274(3) 0.63050(10) -0.25712(7) 0.0341(3) Uani 1 1 d . . . . .
C19 C 1.9263(3) 0.62874(12) -0.32376(9) 0.0529(5) Uani 1 1 d . . . . .
H19A H 2.0027 0.6845 -0.3129 0.064 Uiso 1 1 calc R U . . .
H19B H 1.8101 0.6401 -0.3572 0.064 Uiso 1 1 calc R U . . .
C20 C 2.0927(3) 0.56416(12) -0.34449(8) 0.0494(4) Uani 1 1 d . . . . .
H20A H 2.1992 0.5493 -0.3100 0.074 Uiso 1 1 calc R U . . .
H20B H 2.1746 0.5894 -0.3779 0.074 Uiso 1 1 calc R U . . .
H20C H 2.0139 0.5113 -0.3592 0.074 Uiso 1 1 calc R U . . .


_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 C7 1.7446(15) . ?
S1 C1 1.7685(16) . ?
S2 C14 1.7494(15) . ?
S2 C2 1.7708(16) . ?
O1 C11 1.2056(19) . ?
O2 C11 1.3348(19) . ?
O2 C12 1.4510(19) . ?
O3 C18 1.2035(18) . ?
O4 C18 1.3394(18) . ?
O4 C19 1.4496(19) . ?
C1 C6 1.389(2) . ?
C1 C2 1.401(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.334(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.443(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.331(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.469(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.474(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.334(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.443(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.332(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.471(2) . ?
C17 H17 0.9500 . ?
C19 C20 1.490(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C7 S1 C1 101.29(8) . . ?
C14 S2 C2 100.04(7) . . ?
C11 O2 C12 116.15(13) . . ?
C18 O4 C19 115.86(13) . . ?
C6 C1 C2 119.13(15) . . ?
C6 C1 S1 122.63(13) . . ?
C2 C1 S1 118.23(12) . . ?
C3 C2 C1 119.52(15) . . ?
C3 C2 S2 121.75(13) . . ?
C1 C2 S2 118.72(12) . . ?
C4 C3 C2 120.69(18) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.88(18) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.18(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.54(18) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 S1 123.08(13) . . ?
C8 C7 H7 118.5 . . ?
S1 C7 H7 118.5 . . ?
C7 C8 C9 120.95(15) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 125.71(15) . . ?
C10 C9 H9 117.1 . . ?
C8 C9 H9 117.1 . . ?
C9 C10 C11 120.42(14) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
O1 C11 O2 123.57(14) . . ?
O1 C11 C10 124.73(14) . . ?
O2 C11 C10 111.70(13) . . ?
O2 C12 C13 108.60(15) . . ?
O2 C12 H12A 110.0 . . ?
C13 C12 H12A 110.0 . . ?
O2 C12 H12B 110.0 . . ?
C13 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 S2 124.21(13) . . ?
C15 C14 H14 117.9 . . ?
S2 C14 H14 117.9 . . ?
C14 C15 C16 120.12(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 126.38(15) . . ?
C17 C16 H16 116.8 . . ?
C15 C16 H16 116.8 . . ?
C16 C17 C18 120.01(14) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O3 C18 O4 123.60(14) . . ?
O3 C18 C17 125.05(14) . . ?
O4 C18 C17 111.35(13) . . ?
O4 C19 C20 108.67(14) . . ?
O4 C19 H19A 110.0 . . ?
C20 C19 H19A 110.0 . . ?
O4 C19 H19B 110.0 . . ?
C20 C19 H19B 110.0 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 S1 C1 C6 -29.81(16) . . . . ?
C7 S1 C1 C2 151.39(13) . . . . ?
C6 C1 C2 C3 3.2(2) . . . . ?
S1 C1 C2 C3 -178.00(12) . . . . ?
C6 C1 C2 S2 -178.13(12) . . . . ?
S1 C1 C2 S2 0.71(18) . . . . ?
C14 S2 C2 C3 -28.79(15) . . . . ?
C14 S2 C2 C1 152.53(13) . . . . ?
C1 C2 C3 C4 -2.2(3) . . . . ?
S2 C2 C3 C4 179.10(15) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
S1 C1 C6 C5 179.23(15) . . . . ?
C1 S1 C7 C8 150.66(15) . . . . ?
S1 C7 C8 C9 177.11(12) . . . . ?
C7 C8 C9 C10 175.99(16) . . . . ?
C8 C9 C10 C11 -175.47(15) . . . . ?
C12 O2 C11 O1 0.8(2) . . . . ?
C12 O2 C11 C10 -178.76(14) . . . . ?
C9 C10 C11 O1 1.2(3) . . . . ?
C9 C10 C11 O2 -179.21(14) . . . . ?
C11 O2 C12 C13 -159.05(16) . . . . ?
C2 S2 C14 C15 142.89(15) . . . . ?
S2 C14 C15 C16 178.50(12) . . . . ?
C14 C15 C16 C17 175.40(16) . . . . ?
C15 C16 C17 C18 -175.01(14) . . . . ?
C19 O4 C18 O3 2.4(2) . . . . ?
C19 O4 C18 C17 -177.16(14) . . . . ?
C16 C17 C18 O3 0.2(2) . . . . ?
C16 C17 C18 O4 179.75(13) . . . . ?
C18 O4 C19 C20 -161.36(15) . . . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.035

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535551'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O2 S2'
_chemical_formula_sum            'C16 H14 O2 S2'
_chemical_formula_weight         302.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8437(4)
_cell_length_b                   12.6589(4)
_cell_length_c                   8.7099(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.811(2)
_cell_angle_gamma                90
_cell_volume                     1499.28(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2957
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      67.35

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    3.200
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.418
_exptl_absorpt_correction_T_max  0.521
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            8954
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.773
_diffrn_reflns_theta_max         67.991
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2649
_reflns_number_gt                2126
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+1.1683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2649
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.74188(5) 0.12371(5) 0.04831(7) 0.04060(19) Uani 1 1 d . . . . .
S2 S 0.87280(5) 0.11875(5) 0.37441(7) 0.04164(19) Uani 1 1 d . . . . .
O1 O 0.48735(15) 0.14495(16) -0.7923(2) 0.0556(5) Uani 1 1 d . . . . .
O2 O 1.15501(16) 0.12816(16) 1.1999(2) 0.0584(5) Uani 1 1 d . . . . .
C1 C 0.73091(17) 0.01376(19) 0.1701(3) 0.0343(5) Uani 1 1 d . . . . .
C2 C 0.78911(17) 0.01309(19) 0.3205(3) 0.0340(5) Uani 1 1 d . . . . .
C3 C 0.78196(18) -0.0714(2) 0.4203(3) 0.0390(6) Uani 1 1 d . . . . .
H3 H 0.8216 -0.0727 0.5220 0.047 Uiso 1 1 calc R U . . .
C4 C 0.7174(2) -0.1533(2) 0.3720(3) 0.0458(6) Uani 1 1 d . . . . .
H4 H 0.7125 -0.2104 0.4408 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6599(2) -0.1523(2) 0.2240(3) 0.0467(6) Uani 1 1 d . . . . .
H5 H 0.6160 -0.2091 0.1910 0.056 Uiso 1 1 calc R U . . .
C6 C 0.66627(18) -0.0688(2) 0.1239(3) 0.0406(6) Uani 1 1 d . . . . .
H6 H 0.6260 -0.0680 0.0228 0.049 Uiso 1 1 calc R U . . .
C7 C 0.69604(17) 0.0728(2) -0.1362(3) 0.0381(6) Uani 1 1 d . . . . .
H7 H 0.7055 -0.0001 -0.1552 0.046 Uiso 1 1 calc R U . . .
C8 C 0.64785(18) 0.1326(2) -0.2524(3) 0.0395(6) Uani 1 1 d . . . . .
H8 H 0.6348 0.2043 -0.2313 0.047 Uiso 1 1 calc R U . . .
C9 C 0.61520(17) 0.0928(2) -0.4074(3) 0.0365(5) Uani 1 1 d . . . . .
H9 H 0.6317 0.0220 -0.4278 0.044 Uiso 1 1 calc R U . . .
C10 C 0.56303(18) 0.1482(2) -0.5261(3) 0.0391(6) Uani 1 1 d . . . . .
H10 H 0.5460 0.2196 -0.5102 0.047 Uiso 1 1 calc R U . . .
C11 C 0.53246(18) 0.0998(2) -0.6786(3) 0.0396(6) Uani 1 1 d . . . . .
H11 H 0.5490 0.0277 -0.6900 0.048 Uiso 1 1 calc R U . . .
C12 C 0.88806(18) 0.1154(2) 0.5779(3) 0.0381(5) Uani 1 1 d . . . . .
H12 H 0.8324 0.1015 0.6239 0.046 Uiso 1 1 calc R U . . .
C13 C 0.97473(17) 0.13154(18) 0.6713(3) 0.0355(5) Uani 1 1 d . . . . .
H13 H 1.0308 0.1431 0.6252 0.043 Uiso 1 1 calc R U . . .
C14 C 0.98678(18) 0.13214(18) 0.8387(3) 0.0359(5) Uani 1 1 d . . . . .
H14 H 0.9292 0.1258 0.8827 0.043 Uiso 1 1 calc R U . . .
C15 C 1.07264(18) 0.14085(19) 0.9371(3) 0.0388(6) Uani 1 1 d . . . . .
H15 H 1.1307 0.1539 0.8968 0.047 Uiso 1 1 calc R U . . .
C16 C 1.0791(2) 0.13081(19) 1.1042(3) 0.0432(6) Uani 1 1 d . . . . .
H16 H 1.0192 0.1259 1.1419 0.052 Uiso 1 1 calc R U . . .


_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 C7 1.737(2) . ?
S1 C1 1.774(2) . ?
S2 C12 1.746(2) . ?
S2 C2 1.774(2) . ?
O1 C11 1.210(3) . ?
O2 C16 1.213(3) . ?
C1 C6 1.385(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.338(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.433(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.342(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.452(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.333(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.437(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.333(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.446(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C7 S1 C1 101.79(12) . . ?
C12 S2 C2 101.48(11) . . ?
C6 C1 C2 119.5(2) . . ?
C6 C1 S1 122.78(18) . . ?
C2 C1 S1 117.67(18) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 S2 122.20(18) . . ?
C1 C2 S2 118.32(18) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 S1 122.2(2) . . ?
C8 C7 H7 118.9 . . ?
S1 C7 H7 118.9 . . ?
C7 C8 C9 122.6(2) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C10 C9 C8 124.8(2) . . ?
C10 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
O1 C11 C10 124.4(3) . . ?
O1 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
C13 C12 S2 122.65(19) . . ?
C13 C12 H12 118.7 . . ?
S2 C12 H12 118.7 . . ?
C12 C13 C14 122.7(2) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C15 C14 C13 125.0(2) . . ?
C15 C14 H14 117.5 . . ?
C13 C14 H14 117.5 . . ?
C14 C15 C16 121.3(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
O2 C16 C15 125.2(3) . . ?
O2 C16 H16 117.4 . . ?
C15 C16 H16 117.4 . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1535553'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 O8 S2 + [solvent]'
_chemical_formula_sum            'C24 H26 O8 S2'
_chemical_formula_weight         506.57

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2168(2)
_cell_length_b                   16.2188(4)
_cell_length_c                   25.3953(6)
_cell_angle_alpha                100.6500(10)
_cell_angle_beta                 92.4380(10)
_cell_angle_gamma                101.7140(10)
_cell_volume                     2850.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.36

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48777
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.457
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13088
_reflns_number_gt                8204
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1661P)²+0.7171P] where P=(Fo²+2Fc²)/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_extinction_coef       .
_refine_ls_number_reflns         13088
_refine_ls_number_parameters     617
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   0.812
_refine_ls_restrained_S_all      0.813
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.40769(8) 0.58910(4) 0.38048(2) 0.03161(17) Uani 1 1 d . . . . .
S2 S 0.33193(9) 0.78822(4) 0.35896(3) 0.0425(2) Uani 1 1 d . . . . .
O1 O 0.4620(3) 0.50775(12) 0.36844(8) 0.0450(5) Uani 1 1 d . . . . .
O2 O 0.5444(2) 0.66172(12) 0.40906(7) 0.0429(5) Uani 1 1 d . . . . .
O3 O 0.2690(3) 0.76645(12) 0.40822(9) 0.0545(5) Uani 1 1 d . . . . .
O4 O 0.2362(3) 0.84321(14) 0.33485(11) 0.0628(6) Uani 1 1 d . . . . .
O5 O -0.7631(3) 0.36583(13) 0.48404(8) 0.0463(5) Uani 1 1 d . . . . .
O6 O -0.7477(2) 0.22908(11) 0.48327(7) 0.0399(4) Uani 1 1 d . . . . .
O7 O 1.4721(3) 1.00904(16) 0.25066(11) 0.0685(7) Uani 1 1 d . . . . .
O8 O 1.3998(3) 1.10092(17) 0.20090(11) 0.0738(7) Uani 1 1 d . . . . .
C1 C 0.3397(3) 0.61312(16) 0.31760(9) 0.0278(5) Uani 1 1 d . . . . .
C2 C 0.3154(3) 0.69300(16) 0.30879(10) 0.0326(5) Uani 1 1 d . . . . .
C3 C 0.2725(4) 0.7019(2) 0.25613(13) 0.0480(8) Uani 1 1 d . . . . .
H3 H 0.2576 0.7562 0.2497 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2517(4) 0.6343(3) 0.21377(12) 0.0551(9) Uani 1 1 d . . . . .
H4 H 0.2240 0.6420 0.1783 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2707(4) 0.5554(2) 0.22252(11) 0.0496(8) Uani 1 1 d . . . . .
H5 H 0.2540 0.5082 0.1931 0.059 Uiso 1 1 calc R U . . .
C6 C 0.3144(3) 0.54435(18) 0.27408(10) 0.0373(6) Uani 1 1 d . . . . .
H6 H 0.3272 0.4895 0.2798 0.045 Uiso 1 1 calc R U . . .
C7 C 0.1949(3) 0.57587(16) 0.41144(9) 0.0324(5) Uani 1 1 d . . . . .
H7 H 0.1507 0.6250 0.4278 0.039 Uiso 1 1 calc R U . . .
C8 C 0.0940(3) 0.49788(16) 0.41249(9) 0.0310(5) Uani 1 1 d . . . . .
H8 H 0.1464 0.4495 0.3996 0.037 Uiso 1 1 calc R U . . .
C9 C -0.0916(3) 0.48399(16) 0.43235(9) 0.0315(5) Uani 1 1 d . . . . .
H9 H -0.1437 0.5327 0.4446 0.038 Uiso 1 1 calc R U . . .
C10 C -0.1945(3) 0.40648(16) 0.43450(10) 0.0345(6) Uani 1 1 d . . . . .
H10 H -0.1402 0.3579 0.4240 0.041 Uiso 1 1 calc R U . . .
C11 C -0.3834(3) 0.39295(16) 0.45196(9) 0.0325(5) Uani 1 1 d . . . . .
H11 H -0.4404 0.4413 0.4592 0.039 Uiso 1 1 calc R U . . .
C12 C -0.4840(3) 0.31823(17) 0.45873(10) 0.0369(6) Uani 1 1 d . . . . .
H12 H -0.4301 0.2689 0.4518 0.044 Uiso 1 1 calc R U . . .
C13 C -0.6768(3) 0.30952(17) 0.47673(10) 0.0347(6) Uani 1 1 d . . . . .
C14 C -0.9278(4) 0.21663(18) 0.50725(11) 0.0431(6) Uani 1 1 d . . . . .
H14A H -1.0246 0.2345 0.4857 0.052 Uiso 1 1 calc R U . . .
H14B H -0.9136 0.2513 0.5442 0.052 Uiso 1 1 calc R U . . .
C15 C -0.9861(5) 0.1239(2) 0.50831(14) 0.0592(8) Uani 1 1 d . . . . .
H15A H -1.0105 0.0907 0.4714 0.089 Uiso 1 1 calc R U . . .
H15B H -1.1018 0.1138 0.5271 0.089 Uiso 1 1 calc R U . . .
H15C H -0.8844 0.1059 0.5271 0.089 Uiso 1 1 calc R U . . .
C16 C 0.5742(4) 0.83255(17) 0.36549(12) 0.0421(6) Uani 1 1 d . . . . .
H16 H 0.6575 0.8147 0.3889 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6418(4) 0.89223(17) 0.33709(12) 0.0430(7) Uani 1 1 d . . . . .
H17 H 0.5528 0.9164 0.3197 0.052 Uiso 1 1 calc R U . . .
C18 C 0.8403(4) 0.92238(17) 0.33111(12) 0.0418(6) Uani 1 1 d . . . . .
H18 H 0.9315 0.9058 0.3527 0.050 Uiso 1 1 calc R U . . .
C19 C 0.9015(4) 0.97248(17) 0.29656(12) 0.0435(7) Uani 1 1 d . . . . .
H19 H 0.8127 0.9976 0.2799 0.052 Uiso 1 1 calc R U . . .
C20 C 1.0958(4) 0.99032(17) 0.28332(12) 0.0417(6) Uani 1 1 d . . . . .
H20 H 1.1829 0.9654 0.3008 0.050 Uiso 1 1 calc R U . . .
C21 C 1.1630(4) 1.0384(2) 0.24891(13) 0.0501(7) Uani 1 1 d . . . . .
H21 H 1.0823 1.0681 0.2329 0.060 Uiso 1 1 calc R U . . .
C22 C 1.3609(4) 1.0467(2) 0.23500(14) 0.0532(8) Uani 1 1 d . . . . .
C23 C 1.5898(6) 1.1143(3) 0.1824(2) 0.0958(15) Uani 1 1 d . U . . .
H23A H 1.6366 1.0603 0.1777 0.115 Uiso 1 1 calc R U . . .
H23B H 1.6788 1.1587 0.2089 0.115 Uiso 1 1 calc R U . . .
C24 C 1.5766(10) 1.1422(6) 0.1310(3) 0.193(4) Uani 1 1 d . U . . .
H24A H 1.5185 1.0928 0.1027 0.289 Uiso 1 1 calc R U . . .
H24B H 1.7041 1.1672 0.1222 0.289 Uiso 1 1 calc R U . . .
H24C H 1.4984 1.1854 0.1337 0.289 Uiso 1 1 calc R U . . .
S3 S 0.79116(10) 0.40858(5) 0.23497(3) 0.0491(2) Uani 1 1 d . . . . .
S4 S 0.66522(9) 0.51798(6) 0.13602(3) 0.0505(2) Uani 1 1 d . . . . .
O9 O 0.8599(4) 0.38208(14) 0.18390(11) 0.0722(7) Uani 1 1 d . . . . .
O10 O 0.8913(3) 0.39698(16) 0.28259(11) 0.0692(7) Uani 1 1 d . . . . .
O11 O 0.5418(3) 0.43583(18) 0.13387(8) 0.0741(8) Uani 1 1 d . . . . .
O12 O 0.5908(3) 0.5813(2) 0.11477(9) 0.0762(8) Uani 1 1 d . . . . .
O13 O -0.3852(3) 0.18398(15) 0.32977(10) 0.0596(6) Uani 1 1 d . . . . .
O14 O -0.3227(3) 0.11878(12) 0.39637(7) 0.0431(5) Uani 1 1 d . . . . .
O15 O 1.7752(3) 0.64038(18) -0.02666(10) 0.0707(7) Uani 1 1 d . . . . .
O16 O 1.7117(3) 0.73864(16) -0.07196(10) 0.0680(7) Uani 1 1 d . . . . .
C25 C 0.7890(3) 0.51942(16) 0.24437(9) 0.0304(5) Uani 1 1 d . . . . .
C26 C 0.7426(3) 0.56342(17) 0.20470(9) 0.0319(5) Uani 1 1 d . . . . .
C27 C 0.7521(4) 0.65125(19) 0.21934(13) 0.0461(7) Uani 1 1 d . . . . .
H27 H 0.7234 0.6818 0.1926 0.055 Uiso 1 1 calc R U . . .
C28 C 0.8015(4) 0.6949(2) 0.27121(15) 0.0554(8) Uani 1 1 d . . . . .
H28 H 0.8082 0.7550 0.2800 0.066 Uiso 1 1 calc R U . . .
C29 C 0.8404(4) 0.6525(2) 0.30971(13) 0.0548(9) Uani 1 1 d . . . . .
H29 H 0.8721 0.6826 0.3458 0.066 Uiso 1 1 calc R U . . .
C30 C 0.8344(3) 0.5645(2) 0.29693(10) 0.0427(7) Uani 1 1 d . . . . .
H30 H 0.8616 0.5352 0.3244 0.051 Uiso 1 1 calc R U . . .
C31 C 0.5511(4) 0.36204(18) 0.23455(13) 0.0473(7) Uani 1 1 d . . . . .
H31 H 0.4676 0.3589 0.2040 0.057 Uiso 1 1 calc R U . . .
C32 C 0.4828(4) 0.33077(18) 0.27656(13) 0.0452(7) Uani 1 1 d . . . . .
H32 H 0.5696 0.3290 0.3053 0.054 Uiso 1 1 calc R U . . .
C33 C 0.2834(4) 0.29970(17) 0.28003(12) 0.0404(6) Uani 1 1 d . . . . .
H33 H 0.1969 0.3065 0.2527 0.048 Uiso 1 1 calc R U . . .
C34 C 0.2130(4) 0.26188(17) 0.31938(11) 0.0390(6) Uani 1 1 d . . . . .
H34 H 0.2987 0.2531 0.3462 0.047 Uiso 1 1 calc R U . . .
C35 C 0.0124(4) 0.23385(17) 0.32280(11) 0.0369(6) Uani 1 1 d . . . . .
H35 H -0.0708 0.2477 0.2974 0.044 Uiso 1 1 calc R U . . .
C36 C -0.0664(4) 0.19017(17) 0.35855(11) 0.0382(6) Uani 1 1 d . . . . .
H36 H 0.0126 0.1750 0.3844 0.046 Uiso 1 1 calc R U . . .
C37 C -0.2726(4) 0.16515(17) 0.35863(10) 0.0366(6) Uani 1 1 d . . . . .
C38 C -0.5225(4) 0.08555(19) 0.39787(12) 0.0459(7) Uani 1 1 d . . . . .
H38A H -0.5719 0.0413 0.3652 0.055 Uiso 1 1 calc R U . . .
H38B H -0.5927 0.1323 0.3995 0.055 Uiso 1 1 calc R U . . .
C39 C -0.5466(5) 0.0473(2) 0.44670(15) 0.0658(10) Uani 1 1 d . . . . .
H39A H -0.4716 0.0031 0.4454 0.099 Uiso 1 1 calc R U . . .
H39B H -0.6810 0.0214 0.4480 0.099 Uiso 1 1 calc R U . . .
H39C H -0.5033 0.0923 0.4788 0.099 Uiso 1 1 calc R U . . .
C40 C 0.8767(4) 0.5080(2) 0.10718(10) 0.0474(7) Uani 1 1 d . . . . .
H40 H 0.9371 0.4631 0.1129 0.057 Uiso 1 1 calc R U . . .
C41 C 0.9540(4) 0.5630(2) 0.07707(10) 0.0465(7) Uani 1 1 d . . . . .
H41 H 0.8843 0.6034 0.0687 0.056 Uiso 1 1 calc R U . . .
C42 C 1.1374(4) 0.5645(2) 0.05655(10) 0.0446(7) Uani 1 1 d . . . . .
H42 H 1.2052 0.5225 0.0632 0.054 Uiso 1 1 calc R U . . .
C43 C 1.2157(4) 0.6227(2) 0.02854(11) 0.0466(7) Uani 1 1 d . . . . .
H43 H 1.1444 0.6628 0.0206 0.056 Uiso 1 1 calc R U . . .
C44 C 1.4021(4) 0.6281(2) 0.00966(10) 0.0426(6) Uani 1 1 d . . . . .
H44 H 1.4743 0.5892 0.0188 0.051 Uiso 1 1 calc R U . . .
C45 C 1.4798(4) 0.6833(2) -0.01952(12) 0.0504(7) Uani 1 1 d . . . . .
H45 H 1.4115 0.7238 -0.0284 0.061 Uiso 1 1 calc R U . . .
C46 C 1.6703(4) 0.6836(2) -0.03871(12) 0.0505(7) Uani 1 1 d . . . . .
C47 C 1.8860(6) 0.7367(3) -0.09872(19) 0.0893(13) Uani 1 1 d . U . . .
H47A H 1.9972 0.7531 -0.0719 0.107 Uiso 1 1 calc R U . . .
H47B H 1.8823 0.6782 -0.1193 0.107 Uiso 1 1 calc R U . . .
C48 C 1.9000(8) 0.7977(4) -0.1348(2) 0.131(2) Uani 1 1 d . U . . .
H48A H 1.7837 0.7840 -0.1590 0.196 Uiso 1 1 calc R U . . .
H48B H 2.0093 0.7938 -0.1561 0.196 Uiso 1 1 calc R U . . .
H48C H 1.9164 0.8560 -0.1137 0.196 Uiso 1 1 calc R U . . .


_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 O2 1.4279(19) . ?
S1 O1 1.4349(19) . ?
S1 C7 1.747(2) . ?
S1 C1 1.784(2) . ?
S2 O3 1.429(2) . ?
S2 O4 1.437(2) . ?
S2 C16 1.739(3) . ?
S2 C2 1.791(3) . ?
O5 C13 1.197(3) . ?
O6 C13 1.344(3) . ?
O6 C14 1.452(3) . ?
O7 C22 1.199(4) . ?
O8 C22 1.343(4) . ?
O8 C23 1.456(4) . ?
C1 C6 1.394(4) . ?
C1 C2 1.398(3) . ?
C2 C3 1.400(4) . ?
C3 C4 1.366(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.331(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.440(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.336(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.439(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.325(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.471(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.483(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.338(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.441(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.333(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.441(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.319(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.472(4) . ?
C21 H21 0.9500 . ?
C23 C24 1.464(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
S3 O9 1.431(2) . ?
S3 O10 1.444(2) . ?
S3 C31 1.742(3) . ?
S3 C25 1.773(3) . ?
S4 O11 1.435(2) . ?
S4 O12 1.428(3) . ?
S4 C40 1.745(3) . ?
S4 C26 1.781(3) . ?
O13 C37 1.193(3) . ?
O14 C37 1.342(3) . ?
O14 C38 1.438(3) . ?
O15 C46 1.196(4) . ?
O16 C46 1.339(4) . ?
O16 C47 1.458(4) . ?
C25 C30 1.389(4) . ?
C25 C26 1.404(3) . ?
C26 C27 1.391(4) . ?
C27 C28 1.370(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.346(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.335(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.437(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.333(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.438(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.329(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.461(4) . ?
C36 H36 0.9500 . ?
C38 C39 1.487(4) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.334(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.440(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.335(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.438(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.319(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.478(4) . ?
C45 H45 0.9500 . ?
C47 C48 1.460(6) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?

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
O2 S1 O1 118.39(11) . . ?
O2 S1 C7 111.52(12) . . ?
O1 S1 C7 108.78(12) . . ?
O2 S1 C1 107.53(11) . . ?
O1 S1 C1 106.51(11) . . ?
C7 S1 C1 102.85(11) . . ?
O3 S2 O4 117.73(13) . . ?
O3 S2 C16 111.11(15) . . ?
O4 S2 C16 108.20(13) . . ?
O3 S2 C2 110.33(12) . . ?
O4 S2 C2 106.13(14) . . ?
C16 S2 C2 102.10(12) . . ?
C13 O6 C14 115.5(2) . . ?
C22 O8 C23 117.2(3) . . ?
C6 C1 C2 119.1(2) . . ?
C6 C1 S1 114.67(19) . . ?
C2 C1 S1 126.17(19) . . ?
C1 C2 C3 118.7(3) . . ?
C1 C2 S2 126.46(19) . . ?
C3 C2 S2 114.8(2) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 S1 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
S1 C7 H7 119.5 . . ?
C7 C8 C9 122.6(2) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C10 C9 C8 123.7(2) . . ?
C10 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C9 C10 C11 123.3(2) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C12 C11 C10 125.0(2) . . ?
C12 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
O5 C13 O6 123.4(2) . . ?
O5 C13 C12 125.1(2) . . ?
O6 C13 C12 111.4(2) . . ?
O6 C14 C15 107.2(2) . . ?
O6 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O6 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S2 119.1(2) . . ?
C17 C16 H16 120.5 . . ?
S2 C16 H16 120.5 . . ?
C16 C17 C18 124.4(3) . . ?
C16 C17 H17 117.8 . . ?
C18 C17 H17 117.8 . . ?
C19 C18 C17 122.8(3) . . ?
C19 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C18 C19 C20 123.1(3) . . ?
C18 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C21 C20 C19 125.5(3) . . ?
C21 C20 H20 117.3 . . ?
C19 C20 H20 117.3 . . ?
C20 C21 C22 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
O7 C22 O8 124.1(3) . . ?
O7 C22 C21 125.2(3) . . ?
O8 C22 C21 110.7(3) . . ?
O8 C23 C24 107.0(4) . . ?
O8 C23 H23A 110.3 . . ?
C24 C23 H23A 110.3 . . ?
O8 C23 H23B 110.3 . . ?
C24 C23 H23B 110.3 . . ?
H23A C23 H23B 108.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O9 S3 O10 118.35(15) . . ?
O9 S3 C31 110.51(16) . . ?
O10 S3 C31 109.04(14) . . ?
O9 S3 C25 109.06(12) . . ?
O10 S3 C25 106.46(14) . . ?
C31 S3 C25 102.12(12) . . ?
O11 S4 O12 118.10(16) . . ?
O11 S4 C40 111.71(16) . . ?
O12 S4 C40 108.38(14) . . ?
O11 S4 C26 107.91(12) . . ?
O12 S4 C26 106.56(15) . . ?
C40 S4 C26 102.99(12) . . ?
C37 O14 C38 116.6(2) . . ?
C46 O16 C47 116.0(3) . . ?
C30 C25 C26 118.7(2) . . ?
C30 C25 S3 114.8(2) . . ?
C26 C25 S3 126.4(2) . . ?
C27 C26 C25 118.5(2) . . ?
C27 C26 S4 114.9(2) . . ?
C25 C26 S4 126.7(2) . . ?
C28 C27 C26 121.8(3) . . ?
C28 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C29 C28 C27 119.9(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.4(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C25 C30 C29 120.6(3) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C32 C31 S3 121.0(3) . . ?
C32 C31 H31 119.5 . . ?
S3 C31 H31 119.5 . . ?
C31 C32 C33 122.7(3) . . ?
C31 C32 H32 118.7 . . ?
C33 C32 H32 118.7 . . ?
C34 C33 C32 123.7(3) . . ?
C34 C33 H33 118.1 . . ?
C32 C33 H33 118.1 . . ?
C33 C34 C35 122.6(3) . . ?
C33 C34 H34 118.7 . . ?
C35 C34 H34 118.7 . . ?
C36 C35 C34 125.5(3) . . ?
C36 C35 H35 117.3 . . ?
C34 C35 H35 117.3 . . ?
C35 C36 C37 121.0(2) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
O13 C37 O14 123.1(2) . . ?
O13 C37 C36 125.3(2) . . ?
O14 C37 C36 111.6(2) . . ?
O14 C38 C39 107.3(3) . . ?
O14 C38 H38A 110.2 . . ?
C39 C38 H38A 110.2 . . ?
O14 C38 H38B 110.2 . . ?
C39 C38 H38B 110.2 . . ?
H38A C38 H38B 108.5 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 S4 120.3(3) . . ?
C41 C40 H40 119.9 . . ?
S4 C40 H40 119.9 . . ?
C40 C41 C42 123.5(3) . . ?
C40 C41 H41 118.3 . . ?
C42 C41 H41 118.3 . . ?
C43 C42 C41 122.5(3) . . ?
C43 C42 H42 118.8 . . ?
C41 C42 H42 118.8 . . ?
C42 C43 C44 123.6(3) . . ?
C42 C43 H43 118.2 . . ?
C44 C43 H43 118.2 . . ?
C45 C44 C43 124.6(3) . . ?
C45 C44 H44 117.7 . . ?
C43 C44 H44 117.7 . . ?
C44 C45 C46 121.6(3) . . ?
C44 C45 H45 119.2 . . ?
C46 C45 H45 119.2 . . ?
O15 C46 O16 123.7(3) . . ?
O15 C46 C45 125.1(3) . . ?
O16 C46 C45 111.1(3) . . ?
C48 C47 O16 107.5(4) . . ?
C48 C47 H47A 110.2 . . ?
O16 C47 H47A 110.2 . . ?
C48 C47 H47B 110.2 . . ?
O16 C47 H47B 110.2 . . ?
H47A C47 H47B 108.5 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

_refine_diff_density_max         0.754
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.052



