# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2003358'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H34 N2 O4 S2'
_chemical_formula_weight         406.59

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'

_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                   5.1763(4)
_cell_length_b                   8.0757(6)
_cell_length_c                   12.7460(10)
_cell_angle_alpha                92.297(5)
_cell_angle_beta                 98.372(5)
_cell_angle_gamma                96.965(5)
_cell_volume                     522.34(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3313
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_T_max  0.7457
_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            9470
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         28.114
_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             2531
_reflns_number_gt                1819
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0663P)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         2531
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
C1 C 0.1422(5) 0.4039(3) 0.35063(17) 0.0184(5) Uani 1 1 d . . . . .
H1A H -0.007427 0.443059 0.305141 0.022 Uiso 1 1 calc R U . . .
H1B H 0.193154 0.483629 0.413370 0.022 Uiso 1 1 calc R U . . .
C2 C 0.3725(5) 0.4071(3) 0.28900(18) 0.0207(5) Uani 1 1 d . . . . .
H2A H 0.331736 0.317176 0.231714 0.025 Uiso 1 1 calc R U . . .
H2B H 0.530143 0.383690 0.337254 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4351(5) 0.5737(3) 0.24016(17) 0.0213(5) Uani 1 1 d . . . . .
H3A H 0.590274 0.568582 0.203561 0.026 Uiso 1 1 calc R U . . .
H3B H 0.284521 0.590451 0.185913 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7252(4) 0.7194(3) 0.39673(17) 0.0187(5) Uani 1 1 d . . . . .
H4A H 0.882151 0.766938 0.366715 0.022 Uiso 1 1 calc R U . . .
H4B H 0.747564 0.603183 0.414337 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7048(5) 0.8217(3) 0.49741(16) 0.0184(5) Uani 1 1 d . . . . .
H5A H 0.533026 0.785999 0.520412 0.022 Uiso 1 1 calc R U . . .
H5B H 0.710699 0.941068 0.481650 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4739(5) 0.8750(3) 0.26706(17) 0.0188(5) Uani 1 1 d . . . . .
H6A H 0.497743 0.965698 0.323540 0.023 Uiso 1 1 calc R U . . .
H6B H 0.293950 0.872060 0.227386 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6694(5) 0.9207(3) 0.19113(17) 0.0185(5) Uani 1 1 d . . . . .
C8 C 0.8135(5) 1.1240(3) 0.07656(18) 0.0251(6) Uani 1 1 d . . . . .
H8A H 0.777538 1.047005 0.012236 0.030 Uiso 1 1 calc R U . . .
H8B H 0.999077 1.123662 0.109196 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7670(6) 1.2966(3) 0.04761(19) 0.0323(7) Uani 1 1 d . . . . .
H9A H 0.582581 1.295805 0.015963 0.048 Uiso 1 1 calc R U . . .
H9B H 0.881749 1.334867 -0.003680 0.048 Uiso 1 1 calc R U . . .
H9C H 0.806234 1.372210 0.111548 0.048 Uiso 1 1 calc R U . . .
N1 N 0.4893(4) 0.7187(2) 0.31739(14) 0.0184(4) Uani 1 1 d . . . . .
O1 O 0.8279(3) 0.8346(2) 0.16574(12) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.6376(3) 1.0699(2) 0.15173(12) 0.0208(4) Uani 1 1 d . . . . .
S1 S 0.03319(12) 0.20076(8) 0.39521(4) 0.02092(19) 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
C1 C2 1.518(3) . ?
C1 S1 1.810(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.524(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.472(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.467(3) . ?
C4 C5 1.522(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 S1 1.812(2) 2_666 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.444(3) . ?
C6 C7 1.523(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O1 1.208(3) . ?
C7 O2 1.343(3) . ?
C8 O2 1.459(3) . ?
C8 C9 1.494(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C2 C1 S1 114.47(16) . . ?
C2 C1 H1A 108.6 . . ?
S1 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
S1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 113.0(2) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C2 114.13(18) . . ?
N1 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
N1 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 C5 111.10(18) . . ?
N1 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 S1 112.50(16) . 2_666 ?
C4 C5 H5A 109.1 . . ?
S1 C5 H5A 109.1 2_666 . ?
C4 C5 H5B 109.1 . . ?
S1 C5 H5B 109.1 2_666 . ?
H5A C5 H5B 107.8 . . ?
N1 C6 C7 116.93(19) . . ?
N1 C6 H6A 108.1 . . ?
C7 C6 H6A 108.1 . . ?
N1 C6 H6B 108.1 . . ?
C7 C6 H6B 108.1 . . ?
H6A C6 H6B 107.3 . . ?
O1 C7 O2 123.3(2) . . ?
O1 C7 C6 125.8(2) . . ?
O2 C7 C6 110.85(19) . . ?
O2 C8 C9 108.1(2) . . ?
O2 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O2 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 N1 C4 113.69(18) . . ?
C6 N1 C3 112.41(17) . . ?
C4 N1 C3 114.83(18) . . ?
C7 O2 C8 115.13(19) . . ?
C1 S1 C5 101.64(11) . 2_666 ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_[Cu(1)](ClO4)2
_database_code_depnum_ccdc_archive 'CCDC 2003361'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H34 Cl2 Cu N2 O12 S2'
_chemical_formula_weight         669.03

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/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                   9.4305(4)
_cell_length_b                   16.2613(8)
_cell_length_c                   9.6556(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.665(2)
_cell_angle_gamma                90
_cell_volume                     1345.61(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6925
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.48

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             694
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.199
_exptl_absorpt_coefficient_mu    1.227
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_T_max  0.7457
_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            12390
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         28.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3398
_reflns_number_gt                2708
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0317P)²+3.4230P] 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         3398
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C1 C 0.6191(4) 0.5078(2) 0.3453(4) 0.0284(7) Uani 1 1 d . . . . .
H1A H 0.710247 0.472759 0.360535 0.034 Uiso 1 1 calc R U . . .
H1B H 0.634104 0.532025 0.444513 0.034 Uiso 1 1 calc R U . . .
C2 C 0.4703(4) 0.4580(2) 0.2799(4) 0.0269(7) Uani 1 1 d . . . . .
H2A H 0.473393 0.415832 0.355165 0.032 Uiso 1 1 calc R U . . .
H2B H 0.380522 0.494614 0.261908 0.032 Uiso 1 1 calc R U . . .
C3 C 0.2780(3) 0.3901(2) 0.0639(4) 0.0264(7) Uani 1 1 d . . . . .
H3A H 0.213046 0.439930 0.048852 0.032 Uiso 1 1 calc R U . . .
H3B H 0.260221 0.354987 0.138967 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2194(4) 0.3441(2) -0.0855(4) 0.0284(7) Uani 1 1 d . . . . .
H4A H 0.289492 0.296739 -0.073641 0.034 Uiso 1 1 calc R U . . .
H4B H 0.114712 0.321737 -0.106470 0.034 Uiso 1 1 calc R U . . .
C5 C 0.2077(3) 0.3937(2) -0.2235(4) 0.0277(7) Uani 1 1 d . . . . .
H5A H 0.154641 0.446721 -0.227123 0.033 Uiso 1 1 calc R U . . .
H5B H 0.146434 0.362988 -0.318332 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7002(3) 0.36057(19) 0.1472(3) 0.0231(6) Uani 1 1 d . . . . .
C7 C 0.5514(3) 0.34342(19) 0.1658(4) 0.0230(6) Uani 1 1 d . . . . .
H7A H 0.494369 0.298152 0.096309 0.028 Uiso 1 1 calc R U . . .
H7B H 0.578557 0.324793 0.271472 0.028 Uiso 1 1 calc R U . . .
C8 C 0.9465(3) 0.3044(2) 0.1806(4) 0.0270(7) Uani 1 1 d . . . . .
H8A H 0.937086 0.341121 0.095335 0.032 Uiso 1 1 calc R U . . .
H8B H 0.984209 0.250180 0.163759 0.032 Uiso 1 1 calc R U . . .
C9 C 1.0594(4) 0.3401(3) 0.3283(4) 0.0396(9) Uani 1 1 d . . . . .
H9A H 1.028250 0.396506 0.338294 0.059 Uiso 1 1 calc R U . . .
H9B H 1.164226 0.340474 0.330473 0.059 Uiso 1 1 calc R U . . .
H9C H 1.059717 0.306703 0.412901 0.059 Uiso 1 1 calc R U . . .
Cl1 Cl 0.78753(8) 0.35731(5) 0.67107(9) 0.02530(17) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.000000 0.01605(12) Uani 1 2 d S . P . .
N1 N 0.4468(3) 0.41628(16) 0.1333(3) 0.0217(5) Uani 1 1 d . . . . .
O1 O 0.7295(2) 0.42383(13) 0.1013(2) 0.0235(5) Uani 1 1 d . . . . .
O2 O 0.7919(2) 0.29523(13) 0.1858(3) 0.0273(5) Uani 1 1 d . . . . .
O3 O 0.6203(2) 0.36503(15) 0.6037(3) 0.0329(5) Uani 1 1 d . . . . .
O4 O 0.8415(3) 0.34637(16) 0.5523(3) 0.0362(6) Uani 1 1 d . . . . .
O5 O 0.8320(3) 0.28719(15) 0.7705(3) 0.0369(6) Uani 1 1 d . . . . .
O6 O 0.8554(3) 0.43045(15) 0.7562(3) 0.0398(6) Uani 1 1 d . . . . .
S1 S 0.59716(9) 0.58806(5) 0.20762(9) 0.02432(17) 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
C1 C2 1.511(4) . ?
C1 S1 1.812(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.500(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.508(4) . ?
C3 C4 1.510(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.523(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 S1 1.806(3) 3_665 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O1 1.197(4) . ?
C6 O2 1.322(4) . ?
C6 C7 1.514(4) . ?
C7 N1 1.489(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.487(3) . ?
C8 C9 1.496(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
Cl1 O5 1.436(3) . ?
Cl1 O6 1.436(2) . ?
Cl1 O3 1.439(2) . ?
Cl1 O4 1.446(3) . ?
Cu1 N1 2.074(3) 3_665 ?
Cu1 N1 2.074(2) . ?
Cu1 S1 2.3185(8) . ?
Cu1 S1 2.3185(8) 3_665 ?
Cu1 O1 2.325(2) 3_665 ?
Cu1 O1 2.325(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
C2 C1 S1 106.2(2) . . ?
C2 C1 H1A 110.5 . . ?
S1 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
S1 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
N1 C2 C1 112.5(2) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 117.6(2) . . ?
N1 C3 H3A 107.9 . . ?
C4 C3 H3A 107.9 . . ?
N1 C3 H3B 107.9 . . ?
C4 C3 H3B 107.9 . . ?
H3A C3 H3B 107.2 . . ?
C5 C4 C3 116.0(3) . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C3 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 S1 108.3(2) . 3_665 ?
C4 C5 H5A 110.0 . . ?
S1 C5 H5A 110.0 3_665 . ?
C4 C5 H5B 110.0 . . ?
S1 C5 H5B 110.0 3_665 . ?
H5A C5 H5B 108.4 . . ?
O1 C6 O2 124.8(3) . . ?
O1 C6 C7 124.8(3) . . ?
O2 C6 C7 110.4(3) . . ?
N1 C7 C6 113.2(2) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
O2 C8 C9 108.9(3) . . ?
O2 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
O2 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 Cl1 O6 109.81(16) . . ?
O5 Cl1 O3 109.31(15) . . ?
O6 Cl1 O3 109.24(15) . . ?
O5 Cl1 O4 109.34(15) . . ?
O6 Cl1 O4 109.59(16) . . ?
O3 Cl1 O4 109.53(15) . . ?
N1 Cu1 N1 180.0 3_665 . ?
N1 Cu1 S1 91.18(7) 3_665 . ?
N1 Cu1 S1 88.82(7) . . ?
N1 Cu1 S1 88.82(7) 3_665 3_665 ?
N1 Cu1 S1 91.18(7) . 3_665 ?
S1 Cu1 S1 180.0 . 3_665 ?
N1 Cu1 O1 79.22(8) 3_665 3_665 ?
N1 Cu1 O1 100.78(8) . 3_665 ?
S1 Cu1 O1 89.85(6) . 3_665 ?
S1 Cu1 O1 90.15(6) 3_665 3_665 ?
N1 Cu1 O1 100.78(8) 3_665 . ?
N1 Cu1 O1 79.22(8) . . ?
S1 Cu1 O1 90.15(6) . . ?
S1 Cu1 O1 89.85(6) 3_665 . ?
O1 Cu1 O1 180.0 3_665 . ?
C7 N1 C2 109.7(2) . . ?
C7 N1 C3 110.6(2) . . ?
C2 N1 C3 105.1(2) . . ?
C7 N1 Cu1 110.03(18) . . ?
C2 N1 Cu1 108.08(19) . . ?
C3 N1 Cu1 113.17(18) . . ?
C6 O1 Cu1 107.19(18) . . ?
C6 O2 C8 116.4(2) . . ?
C1 S1 C5 104.80(15) . 3_665 ?
C1 S1 Cu1 94.15(11) . . ?
C5 S1 Cu1 101.30(11) 3_665 . ?

_refine_diff_density_max         1.626
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2003359'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H32 Cl2 N2 O6 S2'
_chemical_formula_weight         459.43

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'

_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                   8.2747(5)
_cell_length_b                   8.4428(5)
_cell_length_c                   8.5526(5)
_cell_angle_alpha                64.705(3)
_cell_angle_beta                 89.681(3)
_cell_angle_gamma                71.834(3)
_cell_volume                     507.59(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6405
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.142
_exptl_absorpt_coefficient_mu    0.559
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_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            9216
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.620
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_full        25.242
_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             2508
_reflns_number_gt                2199
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1017P)²+2.2901P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2508
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2080
_refine_ls_wR_factor_gt          0.2021
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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
C1 C 0.0507(4) 0.7084(4) 0.1121(4) 0.0065(6) Uani 1 1 d . . . . .
C2 C 0.1006(4) 0.5290(4) 0.2817(4) 0.0084(6) Uani 1 1 d . . . . .
H2A H 0.191364 0.526902 0.358250 0.010 Uiso 1 1 calc R U . . .
H2B H -0.000527 0.523816 0.343522 0.010 Uiso 1 1 calc R U . . .
C3 C 0.1493(4) 0.1908(4) 0.3951(4) 0.0069(6) Uani 1 1 d . . . . .
H3A H 0.177392 0.089409 0.359308 0.008 Uiso 1 1 calc R U . . .
H3B H 0.028402 0.217797 0.416934 0.008 Uiso 1 1 calc R U . . .
C4 C 0.2650(4) 0.1231(4) 0.5644(4) 0.0090(6) Uani 1 1 d . . . . .
H4A H 0.228260 0.215988 0.610768 0.011 Uiso 1 1 calc R U . . .
H4B H 0.385279 0.107466 0.542482 0.011 Uiso 1 1 calc R U . . .
C5 C 0.2536(4) -0.0658(4) 0.6994(4) 0.0053(5) Uani 1 1 d . . . . .
H5A H 0.295796 -0.158747 0.653690 0.006 Uiso 1 1 calc R U . . .
H5B H 0.131543 -0.050297 0.713133 0.006 Uiso 1 1 calc R U . . .
C6 C 0.3425(4) 0.3415(4) 0.1934(4) 0.0085(6) Uani 1 1 d . . . . .
H6A H 0.423991 0.315433 0.292807 0.010 Uiso 1 1 calc R U . . .
H6B H 0.339731 0.460262 0.094831 0.010 Uiso 1 1 calc R U . . .
C7 C 0.4068(4) 0.1856(4) 0.1392(4) 0.0090(6) Uani 1 1 d . . . . .
H7A H 0.329313 0.215089 0.035347 0.011 Uiso 1 1 calc R U . . .
H7B H 0.403665 0.067960 0.235200 0.011 Uiso 1 1 calc R U . . .
Cl1 Cl 0.30779(17) 0.48597(18) 0.68353(16) 0.0374(3) Uani 1 1 d . . . . .
H1 H 0.102(6) 0.380(6) 0.167(6) 0.008(10) Uiso 1 1 d . . . . .
N1 N 0.1649(3) 0.3632(4) 0.2461(3) 0.0057(5) Uani 1 1 d . . . . .
O1 O 0.0105(3) 0.7101(3) -0.0265(3) 0.0091(5) Uani 1 1 d . . . . .
H1A H 0.016163 0.602412 -0.008403 0.014 Uiso 0.28 1 calc R U P . .
O2 O 0.0501(3) 0.8504(3) 0.1337(3) 0.0085(5) Uani 1 1 d . . . . .
H2 H 0.021857 0.945623 0.036567 0.013 Uiso 0.72 1 calc R U P . .
O3 O 0.3638(4) 0.7675(4) 0.3574(4) 0.0295(7) Uani 1 1 d . . . . .
S1 S 0.62337(10) 0.15384(11) 0.08863(10) 0.0108(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
C1 O1 1.226(4) . ?
C1 O2 1.287(4) . ?
C1 C2 1.519(4) . ?
C2 N1 1.494(4) . ?
C3 N1 1.513(4) . ?
C3 C4 1.519(4) . ?
C4 C5 1.551(4) . ?
C5 S1 1.809(3) 2_656 ?
C6 N1 1.514(4) . ?
C6 C7 1.521(4) . ?
C7 S1 1.806(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
O1 C1 O2 126.2(3) . . ?
O1 C1 C2 120.6(3) . . ?
O2 C1 C2 113.2(3) . . ?
N1 C2 C1 110.6(2) . . ?
N1 C3 C4 114.1(2) . . ?
C3 C4 C5 109.1(2) . . ?
C4 C5 S1 113.1(2) . 2_656 ?
N1 C6 C7 112.6(2) . . ?
C6 C7 S1 111.8(2) . . ?
C2 N1 C3 111.5(2) . . ?
C2 N1 C6 110.5(2) . . ?
C3 N1 C6 114.9(2) . . ?
C7 S1 C5 102.09(14) . 2_656 ?

_refine_diff_density_max         0.949
_refine_diff_density_min         -1.697
_refine_diff_density_rms         0.154


# start Validation Reply Form

_vrf_PLAT041_2                   
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: Hydrogen atoms on disordered water molecules can not be modelled.
;
_vrf_PLAT043_2                   
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..       4.03 Check 
RESPONSE: Hydrogen atoms on disordered water molecules can not be modelled.
;
_vrf_PLAT068_2                   
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)...     Please Check 
RESPONSE: Hydrogen atoms on disordered water molecules can not be modelled.
;
_vrf_PLAT975_2                   
;
PROBLEM: Check Calcd Resid. Dens.  0.77A   From O3              0.95 eA-3  
RESPONSE: Disordered water molecule in unit cell.
;

# end Validation Reply Form
