# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_L1
_database_code_depnum_ccdc_archive 'CCDC 1898671'
loop_
_audit_author_name
_audit_author_address
'In-Hyeok Park'
;National University of Singapore
South Korea
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-12-17 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         ?
_chemical_formula_sum            'C20 H24 O3 S2'
_chemical_formula_weight         376.51

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'

_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                   14.7867(2)
_cell_length_b                   4.62090(10)
_cell_length_c                   27.4643(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.3620(10)
_cell_angle_gamma                90
_cell_volume                     1871.14(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5025
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.301
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9313
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12750
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.487
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3586
_reflns_number_gt                3065
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0434P)²+0.6599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3586
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 -0.11063(3) 0.60261(9) 0.03551(2) 0.03304(13) Uani 1 1 d . . . . .
S2 S 0.12251(2) 0.90200(9) 0.13048(2) 0.03046(12) Uani 1 1 d . . . . .
O1 O -0.34180(7) 0.5518(2) 0.06352(4) 0.0300(3) Uani 1 1 d . . . . .
C3 C -0.23666(11) 0.6160(4) 0.16390(6) 0.0343(4) Uani 1 1 d . . . . .
H3A H -0.2540 0.8230 0.1641 0.041 Uiso 1 1 calc R U . . .
H3B H -0.2125 0.5702 0.1321 0.041 Uiso 1 1 calc R U . . .
O3 O -0.08864(7) 0.7159(3) 0.19788(4) 0.0321(3) Uani 1 1 d . . . . .
C1 C -0.39844(10) 0.3827(4) 0.09233(6) 0.0295(4) Uani 1 1 d . . . . .
H1A H -0.3777 0.1789 0.0933 0.035 Uiso 1 1 calc R U . . .
H1B H -0.4618 0.3879 0.0779 0.035 Uiso 1 1 calc R U . . .
C2 C -0.39329(10) 0.5058(4) 0.14305(6) 0.0314(4) Uani 1 1 d . . . . .
H2A H -0.3986 0.7190 0.1407 0.038 Uiso 1 1 calc R U . . .
H2B H -0.4458 0.4340 0.1599 0.038 Uiso 1 1 calc R U . . .
O2 O -0.31240(7) 0.4366(3) 0.17205(4) 0.0368(3) Uani 1 1 d . . . . .
C4 C -0.16757(10) 0.5494(4) 0.20539(6) 0.0314(4) Uani 1 1 d . . . . .
H4A H -0.1915 0.6013 0.2369 0.038 Uiso 1 1 calc R U . . .
H4B H -0.1528 0.3404 0.2059 0.038 Uiso 1 1 calc R U . . .
C5 C -0.01554(10) 0.6841(3) 0.23163(5) 0.0254(3) Uani 1 1 d . . . . .
C6 C -0.01571(10) 0.4976(4) 0.27112(6) 0.0299(4) Uani 1 1 d . . . . .
H6A H -0.0680 0.3849 0.2760 0.036 Uiso 1 1 calc R U . . .
C7 C 0.06063(11) 0.4760(4) 0.30342(6) 0.0356(4) Uani 1 1 d . . . . .
H7A H 0.0605 0.3476 0.3304 0.043 Uiso 1 1 calc R U . . .
C8 C 0.13670(11) 0.6390(4) 0.29672(6) 0.0378(4) Uani 1 1 d . . . . .
H8A H 0.1888 0.6251 0.3191 0.045 Uiso 1 1 calc R U . . .
C9 C 0.13635(10) 0.8236(4) 0.25695(6) 0.0333(4) Uani 1 1 d . . . . .
H9A H 0.1889 0.9356 0.2523 0.040 Uiso 1 1 calc R U . . .
C10 C 0.06116(10) 0.8490(3) 0.22366(6) 0.0252(3) Uani 1 1 d . . . . .
C11 C 0.06371(11) 1.0499(3) 0.18084(6) 0.0284(4) Uani 1 1 d . . . . .
H11A H 0.0940 1.2320 0.1919 0.034 Uiso 1 1 calc R U . . .
H11B H 0.0007 1.0981 0.1688 0.034 Uiso 1 1 calc R U . . .
C12 C 0.03588(10) 0.6828(3) 0.09845(6) 0.0266(3) Uani 1 1 d . . . . .
H12A H 0.0651 0.5506 0.0760 0.032 Uiso 1 1 calc R U . . .
H12B H 0.0064 0.5624 0.1225 0.032 Uiso 1 1 calc R U . . .
C13 C -0.03634(10) 0.8566(3) 0.06929(6) 0.0293(4) Uani 1 1 d . . . . .
H13A H -0.0080 0.9887 0.0465 0.035 Uiso 1 1 calc R U . . .
H13B H -0.0713 0.9741 0.0915 0.035 Uiso 1 1 calc R U . . .
C14 C -0.20729(9) 0.8273(3) 0.01569(6) 0.0256(3) Uani 1 1 d . . . . .
H14A H -0.2332 0.9187 0.0441 0.031 Uiso 1 1 calc R U . . .
H14B H -0.1890 0.9814 -0.0066 0.031 Uiso 1 1 calc R U . . .
C15 C -0.27533(9) 0.6291(3) -0.01030(6) 0.0228(3) Uani 1 1 d . . . . .
C16 C -0.27149(10) 0.5723(4) -0.05965(6) 0.0291(4) Uani 1 1 d . . . . .
H16A H -0.2284 0.6720 -0.0774 0.035 Uiso 1 1 calc R U . . .
C17 C -0.32910(10) 0.3733(4) -0.08384(6) 0.0336(4) Uani 1 1 d . . . . .
H17A H -0.3254 0.3373 -0.1177 0.040 Uiso 1 1 calc R U . . .
C18 C -0.39162(10) 0.2285(4) -0.05820(6) 0.0327(4) Uani 1 1 d . . . . .
H18A H -0.4307 0.0902 -0.0744 0.039 Uiso 1 1 calc R U . . .
C19 C -0.39810(10) 0.2826(4) -0.00883(6) 0.0298(4) Uani 1 1 d . . . . .
H19A H -0.4418 0.1833 0.0086 0.036 Uiso 1 1 calc R U . . .
C20 C -0.34034(9) 0.4824(3) 0.01487(5) 0.0238(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 C13 1.8139(16) . ?
S1 C14 1.8161(15) . ?
S2 C12 1.8080(15) . ?
S2 C11 1.8217(16) . ?
O1 C20 1.3757(18) . ?
O1 C1 1.4279(17) . ?
C3 O2 1.4247(19) . ?
C3 C4 1.503(2) . ?
O3 C5 1.3773(17) . ?
O3 C4 1.4260(18) . ?
C1 C2 1.501(2) . ?
C2 O2 1.4222(19) . ?
C5 C6 1.385(2) . ?
C5 C10 1.397(2) . ?
C6 C7 1.385(2) . ?
C7 C8 1.378(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.390(2) . ?
C10 C11 1.501(2) . ?
C12 C13 1.516(2) . ?
C14 C15 1.500(2) . ?
C15 C16 1.386(2) . ?
C15 C20 1.401(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.389(2) . ?
C19 C20 1.386(2) . ?

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
C13 S1 C14 102.45(7) . . ?
C12 S2 C11 102.60(7) . . ?
C20 O1 C1 117.64(12) . . ?
O2 C3 C4 104.99(13) . . ?
C5 O3 C4 117.00(12) . . ?
O1 C1 C2 108.45(13) . . ?
O2 C2 C1 114.56(13) . . ?
C2 O2 C3 114.77(12) . . ?
O3 C4 C3 107.23(13) . . ?
O3 C5 C6 123.04(14) . . ?
O3 C5 C10 116.17(13) . . ?
C6 C5 C10 120.78(14) . . ?
C7 C6 C5 119.75(15) . . ?
C8 C7 C6 120.59(16) . . ?
C7 C8 C9 119.19(16) . . ?
C8 C9 C10 121.70(15) . . ?
C9 C10 C5 117.98(15) . . ?
C9 C10 C11 120.07(14) . . ?
C5 C10 C11 121.95(14) . . ?
C10 C11 S2 113.86(11) . . ?
C13 C12 S2 113.89(11) . . ?
C12 C13 S1 107.60(11) . . ?
C15 C14 S1 106.13(10) . . ?
C16 C15 C20 118.13(14) . . ?
C16 C15 C14 120.34(13) . . ?
C20 C15 C14 121.40(13) . . ?
C15 C16 C17 121.62(15) . . ?
C18 C17 C16 119.23(15) . . ?
C17 C18 C19 120.70(15) . . ?
C20 C19 C18 119.50(14) . . ?
O1 C20 C19 123.82(13) . . ?
O1 C20 C15 115.37(13) . . ?
C19 C20 C15 120.80(14) . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_2_sq
_database_code_depnum_ccdc_archive 'CCDC 1898674'
loop_
_audit_author_name
_audit_author_address
'In-Hyeok Park'
;National University of Singapore
South Korea
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-12-17 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         ?
_chemical_formula_sum            'C84 H112 Cl2 Cu2 N2 O26 S8'
_chemical_formula_weight         2020.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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      tetragonal
_space_group_IT_number           87
_space_group_name_H-M_alt        'I 4/m'
_space_group_name_Hall           '-I 4'

_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'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   16.627(9)
_cell_length_b                   16.627(9)
_cell_length_c                   19.050(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5267(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1445
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      21.54

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             2116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.679
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11089
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.626
_diffrn_reflns_theta_max         25.978
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2677
_reflns_number_gt                1682
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1315P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2677
_refine_ls_number_parameters     152
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2234
_refine_ls_wR_factor_gt          0.1995
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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
Cu1 Cu 0.5000 0.5000 0.62966(6) 0.0351(4) Uani 1 4 d S T P . .
Cl1 Cl 0.5000 0.5000 0.5000 0.0393(8) Uani 1 8 d S T P . .
Cl2 Cl 0.5000 0.5000 0.9216(4) 0.098(2) Uani 0.5 4 d S T P . .
S1 S 0.43149(9) 0.66643(7) 0.60088(7) 0.0466(4) Uani 1 1 d . . . . .
O1 O 0.1494(4) 0.7047(5) 0.5000 0.094(2) Uani 1 2 d S T P . .
O2 O 0.2257(3) 0.6936(3) 0.63808(19) 0.0804(15) Uani 1 1 d . . . . .
O3 O 0.4947(2) 0.61624(18) 0.64040(16) 0.0429(8) Uani 1 1 d . . . . .
C1 C 0.1252(5) 0.7461(5) 0.5625(3) 0.100(3) Uani 1 1 d . . . . .
H1A H 0.0671 0.7590 0.5603 0.120 Uiso 1 1 calc R U . . .
H1B H 0.1555 0.7971 0.5672 0.120 Uiso 1 1 calc R U . . .
C2 C 0.1416(5) 0.6936(5) 0.6232(3) 0.096(3) Uani 1 1 d . . . . .
H2A H 0.1115 0.7131 0.6647 0.116 Uiso 1 1 calc R U . . .
H2B H 0.1235 0.6382 0.6128 0.116 Uiso 1 1 calc R U . . .
C3 C 0.2515(4) 0.6572(4) 0.6991(3) 0.0705(19) Uani 1 1 d . . . . .
C4 C 0.2008(4) 0.6094(4) 0.7405(3) 0.075(2) Uani 1 1 d . . . . .
H4 H 0.1462 0.6010 0.7277 0.090 Uiso 1 1 calc R U . . .
C5 C 0.2328(5) 0.5745(4) 0.8012(3) 0.083(2) Uani 1 1 d . . . . .
H5A H 0.2018 0.5958 0.8415 0.099 Uiso 1 1 calc R U . . .
H5B H 0.2213 0.5161 0.7987 0.099 Uiso 1 1 calc R U . . .
C6 C 0.3140(5) 0.5828(5) 0.8176(4) 0.084(2) Uani 1 1 d . . . . .
H6 H 0.3363 0.5563 0.8574 0.101 Uiso 1 1 calc R U . . .
C7 C 0.3623(4) 0.6309(4) 0.7745(3) 0.0727(19) Uani 1 1 d . . . . .
H7 H 0.4174 0.6384 0.7861 0.087 Uiso 1 1 calc R U . . .
C8 C 0.3314(4) 0.6679(4) 0.7153(3) 0.0669(18) Uani 1 1 d . . . . .
C9 C 0.3830(4) 0.7217(3) 0.6712(3) 0.0697(19) Uani 1 1 d . . . . .
H9A H 0.4245 0.7470 0.7012 0.084 Uiso 1 1 calc R U . . .
H9B H 0.3494 0.7650 0.6509 0.084 Uiso 1 1 calc R U . . .
C10 C 0.4907(4) 0.7480(3) 0.5673(3) 0.0594(16) Uani 1 1 d . . . . .
H10A H 0.4549 0.7944 0.5582 0.071 Uiso 1 1 calc R U . . .
H10B H 0.5298 0.7646 0.6038 0.071 Uiso 1 1 calc R U . . .
C11 C 0.5366(5) 0.7281(5) 0.5000 0.060(2) Uani 1 2 d S T P . .
H11A H 0.5497 0.6701 0.5000 0.071 Uiso 1 2 calc R U P . .
H11B H 0.5880 0.7582 0.5000 0.071 Uiso 1 2 calc R U P . .
O4 O -0.0571(13) 0.5011(19) 0.6314(12) 0.299(10) Uani 0.5 1 d D U P . .
O5 O 0.0000 0.5000 0.7500 0.299(10) Uani 1 4 d DS TU P . .
N1 N 0.0000 0.5000 0.6802(6) 0.197(16) Uani 0.5 2 d DS TU P . .


_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
Cu1 O3 1.945(3) . ?
Cu1 O3 1.946(3) 4_565 ?
Cu1 O3 1.946(3) 3_655 ?
Cu1 O3 1.946(3) 2_665 ?
Cu1 Cl1 2.4699(17) . ?
Cl1 Cu1 2.4699(18) 9_666 ?
S1 O3 1.539(3) . ?
S1 C10 1.794(6) . ?
S1 C9 1.814(6) . ?
O1 C1 1.434(7) . ?
O1 C1 1.434(7) 10_556 ?
O2 C3 1.378(7) . ?
O2 C2 1.426(8) . ?
C1 C2 1.474(9) . ?
C3 C8 1.376(10) . ?
C3 C4 1.402(10) . ?
C4 C5 1.399(8) . ?
C5 C6 1.394(10) . ?
C6 C7 1.400(9) . ?
C7 C8 1.384(8) . ?
C8 C9 1.496(9) . ?
C10 C11 1.528(7) . ?
C11 C10 1.528(7) 10_556 ?
O4 N1 1.329(11) . ?
O5 O5 0.0000 2_565 ?
O5 N1 1.329(11) 15_456 ?
O5 N1 1.329(11) . ?
N1 O4 1.329(11) 2_565 ?
N1 O5 1.329(11) 2_565 ?

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
O3 Cu1 O3 89.37(2) . 4_565 ?
O3 Cu1 O3 89.37(2) . 3_655 ?
O3 Cu1 O3 167.93(19) 4_565 3_655 ?
O3 Cu1 O3 167.92(19) . 2_665 ?
O3 Cu1 O3 89.37(2) 4_565 2_665 ?
O3 Cu1 O3 89.37(2) 3_655 2_665 ?
O3 Cu1 Cl1 96.04(9) . . ?
O3 Cu1 Cl1 96.04(9) 4_565 . ?
O3 Cu1 Cl1 96.04(9) 3_655 . ?
O3 Cu1 Cl1 96.04(9) 2_665 . ?
Cu1 Cl1 Cu1 180.0 9_666 . ?
O3 S1 C10 102.1(3) . . ?
O3 S1 C9 102.5(2) . . ?
C10 S1 C9 97.2(3) . . ?
C1 O1 C1 112.4(6) . 10_556 ?
C3 O2 C2 118.2(6) . . ?
S1 O3 Cu1 121.20(19) . . ?
O1 C1 C2 108.4(6) . . ?
O2 C2 C1 109.7(7) . . ?
C8 C3 O2 115.7(6) . . ?
C8 C3 C4 121.8(6) . . ?
O2 C3 C4 122.5(7) . . ?
C5 C4 C3 118.2(7) . . ?
C6 C5 C4 120.8(7) . . ?
C5 C6 C7 118.7(7) . . ?
C8 C7 C6 121.3(7) . . ?
C3 C8 C7 119.0(7) . . ?
C3 C8 C9 120.3(6) . . ?
C7 C8 C9 120.7(7) . . ?
C8 C9 S1 111.5(4) . . ?
C11 C10 S1 114.2(4) . . ?
C10 C11 C10 114.1(8) . 10_556 ?
O5 O5 N1 0(10) 2_565 15_456 ?
O5 O5 N1 0(10) 2_565 . ?
N1 O5 N1 180.0 15_456 . ?
O4 N1 O4 91(2) 2_565 . ?
O4 N1 O5 134.4(12) 2_565 . ?
O4 N1 O5 134.4(12) . . ?
O4 N1 O5 134.4(12) 2_565 2_565 ?
O4 N1 O5 134.4(12) . 2_565 ?
O5 N1 O5 0.0 . 2_565 ?

_refine_diff_density_max         0.988
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.110




_vrf_PLAT605_2_sq                
;
PROBLEM: Largest Solvent Accessible VOID in the Structure170 A**3 

RESPONSE: SQUEEZE was used because it was impossible to find a disordered solvent molecule.
NMR analysis showed that acetonitrile solvent was present in the lattice. 
;
####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 1898672'
loop_
_audit_author_name
_audit_author_address
'In-Hyeok Park'
;National University of Singapore
South Korea
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-12-17 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         ?
_chemical_formula_sum            'C21 H26 O3 S2'
_chemical_formula_weight         390.54

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9980(2)
_cell_length_b                   13.8621(3)
_cell_length_c                   17.8754(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1981.83(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5155
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.245
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9267
_exptl_absorpt_correction_T_max  0.9331
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17602
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3880
_reflns_number_gt                3520
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0260P)²+0.2647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1384 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3880
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0621
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.38636(9) 0.51551(5) 0.12892(4) 0.03686(17) Uani 1 1 d . . . . .
S2 S 0.38150(8) 0.20074(5) 0.19714(4) 0.03648(17) Uani 1 1 d . . . . .
O1 O 0.0033(2) 0.49276(12) 0.02614(9) 0.0332(4) Uani 1 1 d . . . . .
O2 O -0.14535(19) 0.29419(12) 0.04556(9) 0.0316(4) Uani 1 1 d . . . . .
O3 O -0.0373(2) 0.13047(12) 0.13886(10) 0.0373(4) Uani 1 1 d . . . . .
C1 C -0.1365(3) 0.45131(17) -0.01283(14) 0.0344(6) Uani 1 1 d . . . . .
H1A H -0.0965 0.4157 -0.0574 0.041 Uiso 1 1 calc R U . . .
H1B H -0.2126 0.5031 -0.0299 0.041 Uiso 1 1 calc R U . . .
C2 C -0.2280(3) 0.38443(18) 0.03789(15) 0.0377(6) Uani 1 1 d . . . . .
H2A H -0.2390 0.4147 0.0878 0.045 Uiso 1 1 calc R U . . .
H2B H -0.3419 0.3735 0.0180 0.045 Uiso 1 1 calc R U . . .
C3 C -0.2499(3) 0.22778(19) 0.08418(15) 0.0370(6) Uani 1 1 d . . . . .
H3A H -0.3596 0.2242 0.0587 0.044 Uiso 1 1 calc R U . . .
H3B H -0.2691 0.2513 0.1358 0.044 Uiso 1 1 calc R U . . .
C4 C -0.1745(3) 0.12958(19) 0.08728(14) 0.0362(6) Uani 1 1 d . . . . .
H4A H -0.2595 0.0822 0.1037 0.043 Uiso 1 1 calc R U . . .
H4B H -0.1347 0.1105 0.0370 0.043 Uiso 1 1 calc R U . . .
C5 C 0.0360(3) 0.04357(18) 0.15619(13) 0.0299(6) Uani 1 1 d . . . . .
C6 C -0.0051(3) -0.04344(18) 0.12261(14) 0.0330(6) Uani 1 1 d . . . . .
H6A H -0.0875 -0.0454 0.0844 0.040 Uiso 1 1 calc R U . . .
C7 C 0.0742(3) -0.1276(2) 0.14484(14) 0.0368(6) Uani 1 1 d . . . . .
H7A H 0.0463 -0.1869 0.1213 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1930(3) -0.12625(19) 0.20069(15) 0.0384(6) Uani 1 1 d . . . . .
H8A H 0.2462 -0.1842 0.2162 0.046 Uiso 1 1 calc R U . . .
C9 C 0.2335(3) -0.03878(18) 0.23377(14) 0.0352(6) Uani 1 1 d . . . . .
H9A H 0.3151 -0.0377 0.2724 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1590(3) 0.04671(17) 0.21238(13) 0.0301(6) Uani 1 1 d . . . . .
C11 C 0.2135(3) 0.14004(19) 0.24806(13) 0.0340(6) Uani 1 1 d . . . . .
H11A H 0.2517 0.1267 0.2997 0.041 Uiso 1 1 calc R U . . .
H11B H 0.1161 0.1839 0.2512 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2646(3) 0.28185(19) 0.13702(14) 0.0375(6) Uani 1 1 d . . . . .
H12A H 0.3408 0.3081 0.0984 0.045 Uiso 1 1 calc R U . . .
H12B H 0.1761 0.2448 0.1111 0.045 Uiso 1 1 calc R U . . .
C13 C 0.1845(3) 0.3651(2) 0.17896(16) 0.0420(7) Uani 1 1 d . . . . .
H13A H 0.1246 0.3394 0.2231 0.050 Uiso 1 1 calc R U . . .
H13B H 0.1010 0.3964 0.1461 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3100(4) 0.44042(19) 0.20473(14) 0.0399(6) Uani 1 1 d . . . . .
H14A H 0.4060 0.4074 0.2286 0.048 Uiso 1 1 calc R U . . .
H14B H 0.2568 0.4820 0.2429 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2088(3) 0.59778(18) 0.12127(13) 0.0348(6) Uani 1 1 d . . . . .
H15A H 0.1072 0.5658 0.1410 0.042 Uiso 1 1 calc R U . . .
H15B H 0.2302 0.6559 0.1520 0.042 Uiso 1 1 calc R U . . .
C16 C 0.1793(3) 0.62738(17) 0.04133(13) 0.0288(5) Uani 1 1 d . . . . .
C17 C 0.2523(3) 0.71041(18) 0.01249(15) 0.0354(6) Uani 1 1 d . . . . .
H17A H 0.3234 0.7480 0.0435 0.042 Uiso 1 1 calc R U . . .
C18 C 0.2238(3) 0.73968(19) -0.06039(15) 0.0371(6) Uani 1 1 d . . . . .
H18A H 0.2734 0.7972 -0.0788 0.045 Uiso 1 1 calc R U . . .
C19 C 0.1230(4) 0.68472(18) -0.10596(14) 0.0366(6) Uani 1 1 d . . . . .
H19A H 0.1038 0.7043 -0.1562 0.044 Uiso 1 1 calc R U . . .
C20 C 0.0493(3) 0.60125(18) -0.07942(14) 0.0319(6) Uani 1 1 d . . . . .
H20A H -0.0189 0.5633 -0.1115 0.038 Uiso 1 1 calc R U . . .
C21 C 0.0753(3) 0.57271(17) -0.00533(13) 0.0276(6) 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 C14 1.815(3) . ?
S1 C15 1.827(3) . ?
S2 C12 1.815(3) . ?
S2 C11 1.828(2) . ?
O1 C21 1.370(3) . ?
O1 C1 1.437(3) . ?
O2 C2 1.421(3) . ?
O2 C3 1.422(3) . ?
O3 C5 1.375(3) . ?
O3 C4 1.434(3) . ?
C1 C2 1.489(3) . ?
C3 C4 1.490(4) . ?
C5 C6 1.387(3) . ?
C5 C10 1.407(3) . ?
C6 C7 1.386(4) . ?
C7 C8 1.378(3) . ?
C8 C9 1.387(3) . ?
C9 C10 1.380(3) . ?
C10 C11 1.507(3) . ?
C12 C13 1.518(4) . ?
C13 C14 1.520(4) . ?
C15 C16 1.505(3) . ?
C16 C17 1.390(3) . ?
C16 C21 1.401(3) . ?
C17 C18 1.383(4) . ?
C18 C19 1.376(4) . ?
C19 C20 1.382(3) . ?
C20 C21 1.398(3) . ?

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
C14 S1 C15 98.77(12) . . ?
C12 S2 C11 101.62(12) . . ?
C21 O1 C1 116.83(18) . . ?
C2 O2 C3 110.06(18) . . ?
C5 O3 C4 117.63(18) . . ?
O1 C1 C2 109.6(2) . . ?
O2 C2 C1 112.2(2) . . ?
O2 C3 C4 111.8(2) . . ?
O3 C4 C3 109.0(2) . . ?
O3 C5 C6 124.3(2) . . ?
O3 C5 C10 115.6(2) . . ?
C6 C5 C10 120.1(2) . . ?
C7 C6 C5 120.0(2) . . ?
C8 C7 C6 120.8(2) . . ?
C7 C8 C9 118.8(3) . . ?
C10 C9 C8 122.1(2) . . ?
C9 C10 C5 118.2(2) . . ?
C9 C10 C11 119.7(2) . . ?
C5 C10 C11 122.1(2) . . ?
C10 C11 S2 113.39(17) . . ?
C13 C12 S2 113.34(18) . . ?
C12 C13 C14 113.1(2) . . ?
C13 C14 S1 112.95(18) . . ?
C16 C15 S1 111.28(17) . . ?
C17 C16 C21 118.5(2) . . ?
C17 C16 C15 120.8(2) . . ?
C21 C16 C15 120.7(2) . . ?
C18 C17 C16 121.5(2) . . ?
C19 C18 C17 119.4(2) . . ?
C18 C19 C20 120.7(2) . . ?
C19 C20 C21 119.9(2) . . ?
O1 C21 C20 123.8(2) . . ?
O1 C21 C16 116.3(2) . . ?
C20 C21 C16 119.9(2) . . ?

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1898673'
loop_
_audit_author_name
_audit_author_address
'In-Hyeok Park'
;National University of Singapore
South Korea
;
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-12-17 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         ?
_chemical_formula_sum            'C20 H24 Cu N2 O9 S2'
_chemical_formula_weight         564.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.2239(2)
_cell_length_b                   13.0421(2)
_cell_length_c                   20.8189(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.6790(10)
_cell_angle_gamma                90
_cell_volume                     4676.34(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4122
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      24.82

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             2328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.167
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7442
_exptl_absorpt_correction_T_max  0.8847
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23008
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.959
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4532
_reflns_number_gt                3159
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0356P)²+2.1828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4532
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Cu1 Cu 0.0000 0.5000 0.0000 0.02348(15) Uani 1 2 d S . P A .
Cu2 Cu -0.2500 0.7500 0.0000 0.02342(15) Uani 1 2 d S . P . .
S1 S 0.08192(5) 0.61315(6) -0.05351(5) 0.0374(2) Uani 1 1 d . . . . .
S2 S 0.09126(5) 0.50005(7) 0.08484(4) 0.0334(2) Uani 1 1 d . . . . .
O1 O 0.09292(15) 0.89677(16) -0.00099(11) 0.0449(7) Uani 1 1 d . . . . .
O2 O 0.11350(13) 0.90221(16) 0.13499(11) 0.0346(6) Uani 1 1 d . . . . .
O3 O 0.09716(13) 0.71511(16) 0.20962(11) 0.0349(6) Uani 1 1 d . . . . .
O4 O -0.05589(12) 0.63769(16) 0.06112(11) 0.0342(6) Uani 1 1 d . . . . .
O5 O -0.17475(12) 0.64519(15) 0.02683(11) 0.0303(5) Uani 1 1 d . . . . .
O6 O -0.11737(13) 0.78160(16) 0.06466(12) 0.0379(6) Uani 1 1 d . . . . .
O7 O -0.32430(12) 0.70002(16) 0.06278(11) 0.0323(5) Uani 1 1 d . . . . .
O8 O -0.36762(14) 0.73191(17) 0.15756(11) 0.0406(6) Uani 1 1 d . . . . .
O9 O -0.27129(13) 0.82085(17) 0.11996(12) 0.0388(6) Uani 1 1 d . . . . .
N1 N -0.11486(14) 0.6901(2) 0.05151(13) 0.0267(6) Uani 1 1 d . . . . .
N2 N -0.32080(15) 0.7530(2) 0.11548(14) 0.0279(6) Uani 1 1 d . . . . .
C1 C 0.0749(2) 0.9789(2) 0.09791(17) 0.0356(8) Uani 1 1 d . . . . .
H1A H 0.0778 1.0455 0.1206 0.043 Uiso 1 1 calc R U . . .
H1B H 0.0195 0.9605 0.0923 0.043 Uiso 1 1 calc R U . . .
C2 C 0.1120(2) 0.9882(2) 0.03390(17) 0.0370(9) Uani 1 1 d . . . . .
H2A H 0.0920 1.0493 0.0109 0.044 Uiso 1 1 calc R U . . .
H2B H 0.1690 0.9949 0.0389 0.044 Uiso 1 1 calc R U . . .
C3 C 0.11179(19) 0.8933(2) -0.06426(15) 0.0308(8) Uani 1 1 d . . . . .
C4 C 0.1579(2) 0.9652(2) -0.09548(18) 0.0397(9) Uani 1 1 d . . . . .
H4 H 0.1783 1.0222 -0.0724 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1738(2) 0.9538(3) -0.15942(18) 0.0439(10) Uani 1 1 d . . . . .
H5 H 0.2066 1.0020 -0.1799 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1431(2) 0.8736(2) -0.19462(17) 0.0436(10) Uani 1 1 d . . . . .
H6 H 0.1539 0.8665 -0.2390 0.052 Uiso 1 1 calc R U . . .
C7 C 0.0960(2) 0.8035(2) -0.16368(17) 0.0383(9) Uani 1 1 d . . . . .
H7 H 0.0740 0.7486 -0.1877 0.046 Uiso 1 1 calc R U . . .
C8 C 0.07999(18) 0.8110(2) -0.09901(16) 0.0295(8) Uani 1 1 d . . . . .
C9 C 0.03019(18) 0.7331(2) -0.06608(16) 0.0296(8) Uani 1 1 d . . . . .
H9A H -0.0170 0.7202 -0.0925 0.036 Uiso 1 1 calc R U . . .
H9B H 0.0136 0.7606 -0.0241 0.036 Uiso 1 1 calc R U . . .
C10 C 0.1598(3) 0.6357(4) -0.0010(3) 0.0316(17) Uani 0.698(11) 1 d . . P A 1
H10A H 0.2001 0.5827 -0.0074 0.038 Uiso 0.698(11) 1 calc R U P A 1
H10B H 0.1830 0.7033 -0.0106 0.038 Uiso 0.698(11) 1 calc R U P A 1
C11 C 0.1339(4) 0.6337(6) 0.0677(3) 0.0294(16) Uani 0.698(11) 1 d . . P A 1
H11A H 0.0941 0.6872 0.0747 0.035 Uiso 0.698(11) 1 calc R U P A 1
H11B H 0.1785 0.6474 0.0968 0.035 Uiso 0.698(11) 1 calc R U P A 1
C10X C 0.1257(7) 0.6698(9) 0.0315(7) 0.024(4) Uani 0.302(11) 1 d . . P A 2
H10C H 0.1671 0.7207 0.0233 0.029 Uiso 0.302(11) 1 calc R U P A 2
H10D H 0.0842 0.7033 0.0565 0.029 Uiso 0.302(11) 1 calc R U P A 2
C11X C 0.1584(7) 0.5774(11) 0.0679(6) 0.023(3) Uani 0.302(11) 1 d . . P A 2
H11C H 0.1844 0.6009 0.1080 0.027 Uiso 0.302(11) 1 calc R U P A 2
H11D H 0.1975 0.5424 0.0412 0.027 Uiso 0.302(11) 1 calc R U P A 2
C12 C 0.04354(17) 0.5319(2) 0.15976(15) 0.0272(7) Uani 1 1 d . . . . .
H12A H 0.0177 0.5993 0.1553 0.033 Uiso 1 1 calc R U . . .
H12B H 0.0031 0.4800 0.1686 0.033 Uiso 1 1 calc R U . . .
C13 C 0.10006(17) 0.5357(2) 0.21525(15) 0.0254(7) Uani 1 1 d . . . . .
C14 C 0.12783(18) 0.4464(3) 0.24336(15) 0.0301(8) Uani 1 1 d . . . . .
H14 H 0.1110 0.3820 0.2270 0.036 Uiso 1 1 calc R U . . .
C15 C 0.17919(19) 0.4488(3) 0.29435(16) 0.0347(8) Uani 1 1 d . . . . .
H15 H 0.1982 0.3868 0.3126 0.042 Uiso 1 1 calc R U . . .
C16 C 0.20299(19) 0.5425(3) 0.31889(17) 0.0402(9) Uani 1 1 d . . . . .
H16 H 0.2379 0.5447 0.3545 0.048 Uiso 1 1 calc R U . . .
C17 C 0.17632(18) 0.6329(3) 0.29196(16) 0.0332(8) Uani 1 1 d . . . . .
H17 H 0.1929 0.6970 0.3090 0.040 Uiso 1 1 calc R U . . .
C18 C 0.12533(17) 0.6298(2) 0.24005(15) 0.0259(7) Uani 1 1 d . . . . .
C19 C 0.1203(2) 0.8131(2) 0.23450(16) 0.0379(9) Uani 1 1 d . . . . .
H19A H 0.1773 0.8212 0.2313 0.045 Uiso 1 1 calc R U . . .
H19B H 0.1060 0.8188 0.2803 0.045 Uiso 1 1 calc R U . . .
C20 C 0.0802(2) 0.8936(2) 0.19626(17) 0.0422(9) Uani 1 1 d . . . . .
H20A H 0.0245 0.8762 0.1916 0.051 Uiso 1 1 calc R U . . .
H20B H 0.0843 0.9601 0.2189 0.051 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
Cu1 S1 2.3338(8) . ?
Cu1 S1 2.3339(8) 5_565 ?
Cu1 S2 2.3505(8) . ?
Cu1 S2 2.3505(8) 5_565 ?
Cu1 O4 2.408(2) . ?
Cu1 O4 2.408(2) 5_565 ?
Cu2 O7 1.952(2) 7_465 ?
Cu2 O7 1.952(2) . ?
Cu2 O5 1.9605(19) . ?
Cu2 O5 1.9605(19) 7_465 ?
S1 C10 1.745(5) . ?
S1 C9 1.818(3) . ?
S1 C10X 2.053(13) . ?
S2 C11X 1.578(11) . ?
S2 C12 1.820(3) . ?
S2 C11 1.927(6) . ?
O1 C3 1.361(4) . ?
O1 C2 1.432(4) . ?
O2 C20 1.409(4) . ?
O2 C1 1.423(4) . ?
O3 C18 1.367(3) . ?
O3 C19 1.433(4) . ?
O4 N1 1.239(3) . ?
O5 N1 1.288(3) . ?
O6 N1 1.225(3) . ?
O7 N2 1.297(3) . ?
O8 N2 1.229(3) . ?
O9 N2 1.232(3) . ?
C1 C2 1.489(5) . ?
C3 C4 1.394(4) . ?
C3 C8 1.402(4) . ?
C4 C5 1.371(5) . ?
C5 C6 1.379(5) . ?
C6 C7 1.385(5) . ?
C7 C8 1.381(5) . ?
C8 C9 1.501(4) . ?
C10 C11 1.503(9) . ?
C10X C11X 1.528(19) . ?
C12 C13 1.503(4) . ?
C13 C14 1.386(4) . ?
C13 C18 1.399(4) . ?
C14 C15 1.374(4) . ?
C15 C16 1.385(5) . ?
C16 C17 1.382(4) . ?
C17 C18 1.385(4) . ?
C19 C20 1.484(4) . ?

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
S1 Cu1 S1 180.0 . 5_565 ?
S1 Cu1 S2 87.47(3) . . ?
S1 Cu1 S2 92.53(3) 5_565 . ?
S1 Cu1 S2 92.53(3) . 5_565 ?
S1 Cu1 S2 87.47(3) 5_565 5_565 ?
S2 Cu1 S2 180.0 . 5_565 ?
S1 Cu1 O4 91.63(6) . . ?
S1 Cu1 O4 88.37(6) 5_565 . ?
S2 Cu1 O4 82.57(5) . . ?
S2 Cu1 O4 97.43(5) 5_565 . ?
S1 Cu1 O4 88.37(6) . 5_565 ?
S1 Cu1 O4 91.63(6) 5_565 5_565 ?
S2 Cu1 O4 97.43(5) . 5_565 ?
S2 Cu1 O4 82.57(5) 5_565 5_565 ?
O4 Cu1 O4 180.00(9) . 5_565 ?
O7 Cu2 O7 180.0 7_465 . ?
O7 Cu2 O5 89.26(9) 7_465 . ?
O7 Cu2 O5 90.74(9) . . ?
O7 Cu2 O5 90.74(9) 7_465 7_465 ?
O7 Cu2 O5 89.26(9) . 7_465 ?
O5 Cu2 O5 180.0 . 7_465 ?
C10 S1 C9 108.5(2) . . ?
C9 S1 C10X 89.3(4) . . ?
C10 S1 Cu1 105.78(18) . . ?
C9 S1 Cu1 108.35(11) . . ?
C10X S1 Cu1 92.0(4) . . ?
C11X S2 C12 112.6(5) . . ?
C12 S2 C11 97.5(2) . . ?
C11X S2 Cu1 108.5(5) . . ?
C12 S2 Cu1 109.84(10) . . ?
C11 S2 Cu1 96.5(2) . . ?
C3 O1 C2 117.6(2) . . ?
C20 O2 C1 110.8(2) . . ?
C18 O3 C19 117.5(2) . . ?
N1 O4 Cu1 131.17(18) . . ?
N1 O5 Cu2 108.68(17) . . ?
N2 O7 Cu2 111.35(18) . . ?
O6 N1 O4 122.2(3) . . ?
O6 N1 O5 120.1(2) . . ?
O4 N1 O5 117.7(2) . . ?
O8 N2 O9 124.5(3) . . ?
O8 N2 O7 117.4(3) . . ?
O9 N2 O7 118.2(3) . . ?
O2 C1 C2 109.9(3) . . ?
O1 C2 C1 106.7(3) . . ?
O1 C3 C4 124.9(3) . . ?
O1 C3 C8 115.4(3) . . ?
C4 C3 C8 119.7(3) . . ?
C5 C4 C3 120.1(3) . . ?
C4 C5 C6 121.2(3) . . ?
C5 C6 C7 118.4(3) . . ?
C8 C7 C6 122.1(3) . . ?
C7 C8 C3 118.4(3) . . ?
C7 C8 C9 121.3(3) . . ?
C3 C8 C9 120.3(3) . . ?
C8 C9 S1 111.5(2) . . ?
C11 C10 S1 111.0(4) . . ?
C10 C11 S2 108.1(4) . . ?
C11X C10X S1 105.9(9) . . ?
C10X C11X S2 110.4(10) . . ?
C13 C12 S2 111.8(2) . . ?
C14 C13 C18 118.5(3) . . ?
C14 C13 C12 121.0(3) . . ?
C18 C13 C12 120.6(3) . . ?
C15 C14 C13 121.5(3) . . ?
C14 C15 C16 119.4(3) . . ?
C17 C16 C15 120.5(3) . . ?
C16 C17 C18 119.7(3) . . ?
O3 C18 C17 123.8(3) . . ?
O3 C18 C13 115.9(3) . . ?
C17 C18 C13 120.4(3) . . ?
O3 C19 C20 108.1(3) . . ?
O2 C20 C19 110.5(3) . . ?

_refine_diff_density_max         0.566
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.077

