# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_1539AE051_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1833305'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-07-23 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         'C27 H35 Cl Cu N2 O6 S2, 2(C H2 Cl2)'
_chemical_formula_sum            'C29 H39 Cl5 Cu N2 O6 S2'
_chemical_formula_weight         816.53

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'
Cl Cl 0.1484 0.1585 '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           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                   8.4746(7)
_cell_length_b                   9.5148(7)
_cell_length_c                   45.506(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.765(4)
_cell_angle_gamma                90
_cell_volume                     3667.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6218
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.73

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             1684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.667
_exptl_crystal_size_mid          0.580
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.115
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5205
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            31666
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_theta_min         0.895
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8422
_reflns_number_gt                6549
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0870P)²+8.4728P] 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         8422
_refine_ls_number_parameters     412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1880
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.11052(5) 0.76292(5) 0.35722(2) 0.01673(15) Uani 1 1 d . . . . .
O1 O 0.2786(3) 0.7168(3) 0.38409(6) 0.0191(6) Uani 1 1 d . . . . .
O2 O 0.2180(3) 0.6951(3) 0.32365(6) 0.0181(6) Uani 1 1 d . . . . .
O3 O 0.8568(5) 0.3798(5) 0.39732(8) 0.0532(11) Uani 1 1 d . . . . .
O4 O 0.7846(4) 0.4139(4) 0.34747(9) 0.0421(9) Uani 1 1 d . . . . .
O5 O 0.9908(5) 0.2617(4) 0.36069(9) 0.0481(10) Uani 1 1 d . . . . .
O6 O 1.0246(4) 0.5018(4) 0.36607(8) 0.0381(8) Uani 1 1 d . . . . .
S1 S 0.83591(15) 0.54074(19) 0.54389(3) 0.0458(4) Uani 1 1 d . . . . .
S2 S 0.59923(12) 0.52881(12) 0.14993(2) 0.0248(2) Uani 1 1 d . . . . .
N1 N -0.0050(4) 0.8587(4) 0.39095(8) 0.0211(7) Uani 1 1 d . . . . .
N2 N -0.0753(4) 0.8206(4) 0.33138(7) 0.0204(7) Uani 1 1 d . . . . .
C1 C 0.0948(5) 0.9676(5) 0.40531(10) 0.0295(10) Uani 1 1 d . . . . .
H1A H 0.1177 1.0416 0.3911 0.044 Uiso 1 1 calc R U . . .
H1B H 0.1940 0.9251 0.4126 0.044 Uiso 1 1 calc R U . . .
H1C H 0.0391 1.0083 0.4218 0.044 Uiso 1 1 calc R U . . .
C2 C -0.0450(6) 0.7500(5) 0.41309(10) 0.0301(10) Uani 1 1 d . . . . .
H2A H 0.0520 0.7042 0.4204 0.045 Uiso 1 1 calc R U . . .
H2B H -0.1152 0.6797 0.4039 0.045 Uiso 1 1 calc R U . . .
H2C H -0.0982 0.7946 0.4295 0.045 Uiso 1 1 calc R U . . .
C3 C -0.1522(5) 0.9231(5) 0.37828(10) 0.0275(10) Uani 1 1 d . . . . .
H3A H -0.1315 1.0213 0.3723 0.033 Uiso 1 1 calc R U . . .
H3B H -0.2348 0.9240 0.3932 0.033 Uiso 1 1 calc R U . . .
C4 C -0.2074(5) 0.8391(5) 0.35209(9) 0.0259(9) Uani 1 1 d . . . . .
H4A H -0.2449 0.7459 0.3586 0.031 Uiso 1 1 calc R U . . .
H4B H -0.2966 0.8879 0.3419 0.031 Uiso 1 1 calc R U . . .
C5 C -0.1240(5) 0.7188(5) 0.30837(10) 0.0264(9) Uani 1 1 d . . . . .
H5A H -0.1524 0.6295 0.3176 0.040 Uiso 1 1 calc R U . . .
H5B H -0.0364 0.7034 0.2952 0.040 Uiso 1 1 calc R U . . .
H5C H -0.2153 0.7558 0.2971 0.040 Uiso 1 1 calc R U . . .
C6 C -0.0339(5) 0.9560(5) 0.31705(10) 0.0260(9) Uani 1 1 d . . . . .
H6A H 0.0519 0.9403 0.3035 0.039 Uiso 1 1 calc R U . . .
H6B H 0.0002 1.0241 0.3321 0.039 Uiso 1 1 calc R U . . .
H6C H -0.1265 0.9927 0.3061 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4359(4) 0.5948(4) 0.35015(9) 0.0188(8) Uani 1 1 d . . . . .
H7 H 0.5264 0.5367 0.3484 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4007(4) 0.6432(4) 0.37815(9) 0.0180(8) Uani 1 1 d . . . . .
C9 C 0.5105(5) 0.6116(5) 0.40274(9) 0.0233(9) Uani 1 1 d . . . . .
H9 H 0.5995 0.5534 0.3996 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4869(5) 0.6638(5) 0.42960(10) 0.0278(10) Uani 1 1 d . . . . .
H10 H 0.3999 0.7261 0.4311 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5784(5) 0.6369(5) 0.45696(9) 0.0286(10) Uani 1 1 d . . . . .
C12 C 0.5327(6) 0.7033(7) 0.48247(11) 0.0409(13) Uani 1 1 d . . . . .
H12 H 0.4468 0.7675 0.4815 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6090(6) 0.6784(7) 0.50923(11) 0.0397(13) Uani 1 1 d . . . . .
H13 H 0.5758 0.7256 0.5264 0.048 Uiso 1 1 calc R U . . .
C14 C 0.7325(5) 0.5858(6) 0.51109(10) 0.0334(11) Uani 1 1 d . . . . .
C15 C 0.7820(5) 0.5201(7) 0.48555(10) 0.0377(13) Uani 1 1 d . . . . .
H15 H 0.8687 0.4568 0.4865 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7060(5) 0.5464(6) 0.45884(10) 0.0307(11) Uani 1 1 d . . . . .
H16 H 0.7417 0.5019 0.4416 0.037 Uiso 1 1 calc R U . . .
C17 C 0.7494(6) 0.6502(7) 0.57061(10) 0.0408(13) Uani 1 1 d . . . . .
H17A H 0.7680 0.7490 0.5657 0.061 Uiso 1 1 calc R U . . .
H17B H 0.7970 0.6296 0.5900 0.061 Uiso 1 1 calc R U . . .
H17C H 0.6356 0.6324 0.5708 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3479(4) 0.6254(4) 0.32457(9) 0.0161(8) Uani 1 1 d . . . . .
C19 C 0.4084(4) 0.5792(4) 0.29608(9) 0.0186(8) Uani 1 1 d . . . . .
H19 H 0.4954 0.5162 0.2959 0.022 Uiso 1 1 calc R U . . .
C20 C 0.3450(4) 0.6229(4) 0.27067(8) 0.0175(8) Uani 1 1 d . . . . .
H20 H 0.2527 0.6791 0.2718 0.021 Uiso 1 1 calc R U . . .
C21 C 0.4004(4) 0.5946(4) 0.24111(8) 0.0162(8) Uani 1 1 d . . . . .
C22 C 0.5041(5) 0.4844(4) 0.23502(10) 0.0220(9) Uani 1 1 d . . . . .
H22 H 0.5352 0.4207 0.2502 0.026 Uiso 1 1 calc R U . . .
C23 C 0.5617(5) 0.4672(4) 0.20709(9) 0.0222(9) Uani 1 1 d . . . . .
H23 H 0.6312 0.3915 0.2033 0.027 Uiso 1 1 calc R U . . .
C24 C 0.5191(4) 0.5593(4) 0.18459(9) 0.0190(8) Uani 1 1 d . . . . .
C25 C 0.4129(4) 0.6681(5) 0.19013(9) 0.0202(8) Uani 1 1 d . . . . .
H25 H 0.3805 0.7309 0.1749 0.024 Uiso 1 1 calc R U . . .
C26 C 0.3557(4) 0.6831(5) 0.21807(9) 0.0210(8) Uani 1 1 d . . . . .
H26 H 0.2830 0.7567 0.2216 0.025 Uiso 1 1 calc R U . . .
C27 C 0.5647(10) 0.6910(7) 0.13124(14) 0.066(2) Uani 1 1 d . . . . .
H27A H 0.4509 0.7046 0.1279 0.099 Uiso 1 1 calc R U . . .
H27B H 0.6165 0.6891 0.1123 0.099 Uiso 1 1 calc R U . . .
H27C H 0.6078 0.7685 0.1432 0.099 Uiso 1 1 calc R U . . .
C1S C 0.7617(16) 0.1685(11) 0.4531(3) 0.125(5) Uani 1 1 d . . . . .
H1S1 H 0.8186 0.1851 0.4348 0.151 Uiso 1 1 calc R U . . .
H1S2 H 0.7108 0.2583 0.4585 0.151 Uiso 1 1 calc R U . . .
C2S C 0.9518(5) 0.8693(5) 0.20823(10) 0.0245(9) Uani 1 1 d . . . . .
H2S1 H 0.9024 0.9442 0.1960 0.029 Uiso 1 1 calc R U . . .
H2S2 H 1.0329 0.8226 0.1964 0.029 Uiso 1 1 calc R U . . .
Cl1 Cl 0.91359(11) 0.38863(11) 0.36800(2) 0.0208(2) Uani 1 1 d . . . . .
Cl2 Cl 0.8994(10) 0.1272(8) 0.48054(14) 0.281(4) Uani 1 1 d . . . . .
Cl3 Cl 0.6143(7) 0.0464(4) 0.44575(12) 0.220(3) Uani 1 1 d . . . . .
Cl4 Cl 0.80805(15) 0.74646(14) 0.21743(4) 0.0453(4) Uani 1 1 d . . . . .
Cl5 Cl 1.04326(13) 0.94534(12) 0.23975(2) 0.0291(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
Cu1 O1 1.899(3) . ?
Cu1 O2 1.915(3) . ?
Cu1 N2 2.013(3) . ?
Cu1 N1 2.059(3) . ?
O1 C8 1.285(5) . ?
O2 C18 1.285(5) . ?
O3 Cl1 1.434(3) . ?
O4 Cl1 1.436(4) . ?
O5 Cl1 1.418(4) . ?
O6 Cl1 1.434(3) . ?
S1 C14 1.760(5) . ?
S1 C17 1.776(6) . ?
S2 C24 1.760(4) . ?
S2 C27 1.782(6) . ?
N1 C1 1.477(6) . ?
N1 C3 1.490(5) . ?
N1 C2 1.491(6) . ?
N2 C5 1.476(6) . ?
N2 C6 1.491(6) . ?
N2 C4 1.495(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.498(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C18 1.394(6) . ?
C7 C8 1.396(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.465(6) . ?
C9 C10 1.340(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.469(6) . ?
C10 H10 0.9500 . ?
C11 C16 1.383(7) . ?
C11 C12 1.387(7) . ?
C12 C13 1.382(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.369(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(7) . ?
C15 C16 1.381(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.476(5) . ?
C19 C20 1.327(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.463(5) . ?
C20 H20 0.9500 . ?
C21 C26 1.389(6) . ?
C21 C22 1.401(5) . ?
C22 C23 1.385(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.400(6) . ?
C25 C26 1.382(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C1S Cl2 1.727(15) . ?
C1S Cl3 1.731(14) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S Cl4 1.749(5) . ?
C2S Cl5 1.764(4) . ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?

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 Cu1 O2 94.02(12) . . ?
O1 Cu1 N2 175.38(13) . . ?
O2 Cu1 N2 90.50(13) . . ?
O1 Cu1 N1 89.23(13) . . ?
O2 Cu1 N1 173.22(13) . . ?
N2 Cu1 N1 86.17(14) . . ?
C8 O1 Cu1 125.7(3) . . ?
C18 O2 Cu1 125.2(3) . . ?
C14 S1 C17 103.5(2) . . ?
C24 S2 C27 102.9(2) . . ?
C1 N1 C3 110.2(4) . . ?
C1 N1 C2 109.1(4) . . ?
C3 N1 C2 110.0(3) . . ?
C1 N1 Cu1 111.2(2) . . ?
C3 N1 Cu1 107.8(3) . . ?
C2 N1 Cu1 108.6(3) . . ?
C5 N2 C6 108.7(3) . . ?
C5 N2 C4 109.0(3) . . ?
C6 N2 C4 111.4(3) . . ?
C5 N2 Cu1 115.6(3) . . ?
C6 N2 Cu1 107.5(3) . . ?
C4 N2 Cu1 104.6(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 109.0(4) . . ?
N1 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 110.0(3) . . ?
N2 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C18 C7 C8 124.7(4) . . ?
C18 C7 H7 117.7 . . ?
C8 C7 H7 117.7 . . ?
O1 C8 C7 124.6(4) . . ?
O1 C8 C9 116.6(4) . . ?
C7 C8 C9 118.7(4) . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 128.2(4) . . ?
C9 C10 H10 115.9 . . ?
C11 C10 H10 115.9 . . ?
C16 C11 C12 118.0(4) . . ?
C16 C11 C10 123.5(4) . . ?
C12 C11 C10 118.4(4) . . ?
C13 C12 C11 121.6(5) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 C12 120.1(5) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 S1 124.6(4) . . ?
C15 C14 S1 116.3(4) . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.7(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 C7 124.8(3) . . ?
O2 C18 C19 116.5(3) . . ?
C7 C18 C19 118.7(3) . . ?
C20 C19 C18 122.0(4) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 127.6(4) . . ?
C19 C20 H20 116.2 . . ?
C21 C20 H20 116.2 . . ?
C26 C21 C22 117.6(4) . . ?
C26 C21 C20 119.7(4) . . ?
C22 C21 C20 122.7(4) . . ?
C23 C22 C21 120.7(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.8(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C25 119.2(4) . . ?
C23 C24 S2 117.3(3) . . ?
C25 C24 S2 123.4(3) . . ?
C26 C25 C24 119.2(4) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C21 122.5(4) . . ?
C25 C26 H26 118.8 . . ?
C21 C26 H26 118.8 . . ?
S2 C27 H27A 109.5 . . ?
S2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
S2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Cl2 C1S Cl3 117.0(7) . . ?
Cl2 C1S H1S1 108.0 . . ?
Cl3 C1S H1S1 108.0 . . ?
Cl2 C1S H1S2 108.0 . . ?
Cl3 C1S H1S2 108.0 . . ?
H1S1 C1S H1S2 107.3 . . ?
Cl4 C2S Cl5 111.8(2) . . ?
Cl4 C2S H2S1 109.3 . . ?
Cl5 C2S H2S1 109.3 . . ?
Cl4 C2S H2S2 109.3 . . ?
Cl5 C2S H2S2 109.3 . . ?
H2S1 C2S H2S2 107.9 . . ?
O5 Cl1 O6 108.4(2) . . ?
O5 Cl1 O3 109.8(3) . . ?
O6 Cl1 O3 109.9(2) . . ?
O5 Cl1 O4 109.7(3) . . ?
O6 Cl1 O4 108.8(2) . . ?
O3 Cl1 O4 110.2(2) . . ?

_refine_diff_density_max         1.494
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.191

####################################################################### 
# 
# 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_1563AC073_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1840934'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-07-23 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         'C21 H20 O2 S2'
_chemical_formula_sum            'C21 H20 O2 S2'
_chemical_formula_weight         368.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Zn Zn 0.2839 1.4301 '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                   13.7982(5)
_cell_length_b                   5.5253(2)
_cell_length_c                   24.9052(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.390(2)
_cell_angle_gamma                90
_cell_volume                     1847.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5173
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.61

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.743
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.175
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   0.808
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15846
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.555
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4216
_reflns_number_gt                3074
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0750P)²+0.4004P] 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         4216
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
S2 S 1.31056(5) 0.30859(13) 0.53786(3) 0.0683(2) Uani 1 1 d . . . . .
S1 S 0.05902(4) 0.45669(14) 0.09856(3) 0.0712(2) Uani 1 1 d . . . . .
O2 O 0.78921(12) 1.0894(3) 0.34534(7) 0.0635(4) Uani 1 1 d . . . . .
O1 O 0.61190(13) 1.0920(3) 0.29134(7) 0.0675(5) Uani 1 1 d . . . . .
H1 H 0.6547 1.1291 0.3188 0.101 Uiso 1 1 calc R U . . .
C5 C 0.35368(15) 0.7262(4) 0.20505(7) 0.0435(4) Uani 1 1 d . . . . .
C4 C 0.44540(16) 0.8333(4) 0.23700(8) 0.0485(5) Uani 1 1 d . . . . .
H4 H 0.4395 0.9850 0.2521 0.058 Uiso 1 1 calc R U . . .
C15 C 1.04074(15) 0.6935(4) 0.43144(8) 0.0486(5) Uani 1 1 d . . . . .
C10 C 0.35086(15) 0.5108(4) 0.17572(8) 0.0475(5) Uani 1 1 d . . . . .
H10 H 0.4094 0.4240 0.1781 0.057 Uiso 1 1 calc R U . . .
C6 C 0.26371(16) 0.8470(4) 0.20172(8) 0.0491(5) Uani 1 1 d . . . . .
H6 H 0.2632 0.9896 0.2215 0.059 Uiso 1 1 calc R U . . .
C12 C 0.79486(16) 0.8659(4) 0.33285(8) 0.0506(5) Uani 1 1 d . . . . .
C14 C 0.95328(16) 0.8154(4) 0.39941(8) 0.0522(5) Uani 1 1 d . . . . .
H14 H 0.9453 0.9757 0.4089 0.063 Uiso 1 1 calc R U . . .
C8 C 0.17443(15) 0.5495(4) 0.13945(8) 0.0465(5) Uani 1 1 d . . . . .
C13 C 0.88311(16) 0.7282(4) 0.35824(9) 0.0535(5) Uani 1 1 d . . . . .
H13 H 0.8908 0.5733 0.3452 0.064 Uiso 1 1 calc R U . . .
C2 C 0.62340(16) 0.8667(4) 0.27896(8) 0.0500(5) Uani 1 1 d . . . . .
C7 C 0.17602(16) 0.7596(4) 0.16984(8) 0.0505(5) Uani 1 1 d . . . . .
H7 H 0.1169 0.8427 0.1686 0.061 Uiso 1 1 calc R U . . .
C9 C 0.26326(15) 0.4234(4) 0.14325(8) 0.0482(5) Uani 1 1 d . . . . .
H9 H 0.2634 0.2798 0.1238 0.058 Uiso 1 1 calc R U . . .
C3 C 0.53671(16) 0.7400(4) 0.24718(8) 0.0517(5) Uani 1 1 d . . . . .
H3 H 0.5454 0.5872 0.2333 0.062 Uiso 1 1 calc R U . . .
C18 C 1.20856(15) 0.4686(4) 0.49852(9) 0.0503(5) Uani 1 1 d . . . . .
C1 C 0.71422(16) 0.7515(4) 0.29687(8) 0.0517(5) Uani 1 1 d . . . . .
H1A H 0.7221 0.5950 0.2848 0.062 Uiso 1 1 calc R U . . .
C20 C 1.07621(17) 0.4745(4) 0.41630(9) 0.0576(6) Uani 1 1 d . . . . .
H20 H 1.0433 0.4002 0.3837 0.069 Uiso 1 1 calc R U . . .
C17 C 1.17565(16) 0.6873(4) 0.51363(9) 0.0568(6) Uani 1 1 d . . . . .
H17 H 1.2083 0.7604 0.5465 0.068 Uiso 1 1 calc R U . . .
C16 C 1.09429(16) 0.7985(4) 0.48012(9) 0.0576(6) Uani 1 1 d . . . . .
H16 H 1.0745 0.9490 0.4904 0.069 Uiso 1 1 calc R U . . .
C19 C 1.15861(19) 0.3663(5) 0.44845(10) 0.0614(6) Uani 1 1 d . . . . .
H19 H 1.1818 0.2220 0.4368 0.074 Uiso 1 1 calc R U . . .
C21 C 1.3640(2) 0.5149(5) 0.59140(10) 0.0713(7) Uani 1 1 d . . . . .
H21A H 1.3857 0.6576 0.5756 0.107 Uiso 1 1 calc R U . . .
H21B H 1.4199 0.4400 0.6159 0.107 Uiso 1 1 calc R U . . .
H21C H 1.3151 0.5582 0.6116 0.107 Uiso 1 1 calc R U . . .
C11 C 0.0904(2) 0.2496(6) 0.05079(11) 0.0754(8) Uani 1 1 d . . . . .
H11A H 0.1369 0.3240 0.0326 0.113 Uiso 1 1 calc R U . . .
H11B H 0.0312 0.2052 0.0239 0.113 Uiso 1 1 calc R U . . .
H11C H 0.1198 0.1074 0.0700 0.113 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
S2 C18 1.756(2) . ?
S2 C21 1.779(3) . ?
S1 C8 1.756(2) . ?
S1 C11 1.775(3) . ?
O2 C12 1.280(3) . ?
O1 C2 1.301(3) . ?
O1 H1 0.8200 . ?
C5 C10 1.392(3) . ?
C5 C6 1.395(3) . ?
C5 C4 1.455(3) . ?
C4 C3 1.330(3) . ?
C4 H4 0.9300 . ?
C15 C20 1.390(3) . ?
C15 C16 1.392(3) . ?
C15 C14 1.449(3) . ?
C10 C9 1.377(3) . ?
C10 H10 0.9300 . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C12 C1 1.406(3) . ?
C12 C13 1.451(3) . ?
C14 C13 1.327(3) . ?
C14 H14 0.9300 . ?
C8 C7 1.384(3) . ?
C8 C9 1.394(3) . ?
C13 H13 0.9300 . ?
C2 C1 1.384(3) . ?
C2 C3 1.452(3) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C18 C17 1.374(3) . ?
C18 C19 1.397(3) . ?
C1 H1A 0.9300 . ?
C20 C19 1.368(3) . ?
C20 H20 0.9300 . ?
C17 C16 1.378(3) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C18 S2 C21 103.59(12) . . ?
C8 S1 C11 104.36(11) . . ?
C2 O1 H1 109.5 . . ?
C10 C5 C6 117.48(19) . . ?
C10 C5 C4 123.34(18) . . ?
C6 C5 C4 119.14(19) . . ?
C3 C4 C5 127.7(2) . . ?
C3 C4 H4 116.1 . . ?
C5 C4 H4 116.1 . . ?
C20 C15 C16 116.7(2) . . ?
C20 C15 C14 123.78(19) . . ?
C16 C15 C14 119.5(2) . . ?
C9 C10 C5 121.47(19) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C7 C6 C5 121.29(19) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O2 C12 C1 120.3(2) . . ?
O2 C12 C13 119.48(19) . . ?
C1 C12 C13 120.2(2) . . ?
C13 C14 C15 128.5(2) . . ?
C13 C14 H14 115.8 . . ?
C15 C14 H14 115.8 . . ?
C7 C8 C9 118.68(19) . . ?
C7 C8 S1 117.36(16) . . ?
C9 C8 S1 123.95(17) . . ?
C14 C13 C12 122.3(2) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
O1 C2 C1 120.97(19) . . ?
O1 C2 C3 117.4(2) . . ?
C1 C2 C3 121.6(2) . . ?
C6 C7 C8 120.80(19) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C4 C3 C2 122.8(2) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C17 C18 C19 118.3(2) . . ?
C17 C18 S2 124.27(17) . . ?
C19 C18 S2 117.41(18) . . ?
C2 C1 C12 121.5(2) . . ?
C2 C1 H1A 119.2 . . ?
C12 C1 H1A 119.2 . . ?
C19 C20 C15 121.3(2) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C16 C15 122.4(2) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
S2 C21 H21A 109.5 . . ?
S2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.073

