# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1586815'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H31 Cu2 I2 N S2'
_chemical_formula_weight         682.42

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   16.6274(14)
_cell_length_b                   10.6924(9)
_cell_length_c                   13.1711(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.243(2)
_cell_angle_gamma                90.00
_cell_volume                     2197.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8690
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.51

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_absorpt_coefficient_mu    4.935
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.1687
_exptl_absorpt_correction_T_max  0.5056
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14706
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5031
_reflns_number_gt                4636
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+53.4538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5031
_refine_ls_number_parameters     267
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1561
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.154
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.32825(7) 0.25582(10) 0.16869(9) 0.0206(2) Uani 1 1 d . . .
Cu2 Cu 0.43269(7) 0.44061(10) 0.50551(8) 0.0206(2) Uani 1 1 d . . .
I1 I 0.33486(4) 0.27547(5) 0.37036(4) 0.02252(16) Uani 1 1 d . . .
I2 I 0.41431(4) 0.66834(5) 0.42399(5) 0.02314(16) Uani 1 1 d . . .
S1 S 0.20592(15) 0.3417(2) 0.0479(2) 0.0256(5) Uani 1 1 d . . .
S2 S 0.62011(14) 0.56653(19) 0.35131(16) 0.0182(4) Uani 1 1 d . . .
N1 N 0.4025(5) 0.4018(7) 0.1380(6) 0.0191(14) Uani 1 1 d . . .
H1N H 0.420(7) 0.385(10) 0.086(8) 0.02(2) Uiso 1 1 d . . .
C1 C 0.3441(6) 0.5098(9) 0.1085(8) 0.0240(18) Uani 1 1 d . A .
H1A H 0.3723 0.5793 0.0841 0.029 Uiso 1 1 calc R . .
H1B H 0.3316 0.5385 0.1729 0.029 Uiso 1 1 calc R . .
C2 C 0.2607(6) 0.4767(9) 0.0190(8) 0.0269(19) Uani 1 1 d . A .
H2A H 0.2730 0.4604 -0.0482 0.032 Uiso 1 1 calc R . .
H2B H 0.2218 0.5497 0.0056 0.032 Uiso 1 1 calc R . .
C3 C 0.4810(6) 0.4219(8) 0.2328(7) 0.0213(17) Uani 1 1 d . A .
H3A H 0.5176 0.3466 0.2432 0.026 Uiso 1 1 calc R . .
H3B H 0.4646 0.4312 0.2979 0.026 Uiso 1 1 calc R . .
C4 C 0.5332(6) 0.5352(9) 0.2243(7) 0.0244(18) Uani 1 1 d . . .
H4A H 0.4952 0.6092 0.2040 0.029 Uiso 1 1 calc R A .
H4B H 0.5575 0.5209 0.1664 0.029 Uiso 1 1 calc R . .
C11 C 0.6980(6) 0.4421(8) 0.3631(7) 0.0211(17) Uani 1 1 d . . .
H11 H 0.6703 0.3596 0.3653 0.025 Uiso 1 1 calc R A .
C12 C 0.7704(6) 0.4631(9) 0.4709(8) 0.0250(18) Uani 1 1 d . A .
H12A H 0.7479 0.4562 0.5311 0.030 Uiso 1 1 calc R . .
H12B H 0.7944 0.5482 0.4726 0.030 Uiso 1 1 calc R . .
C13 C 0.8411(7) 0.3655(10) 0.4852(9) 0.032(2) Uani 1 1 d . . .
H13A H 0.8892 0.3830 0.5531 0.039 Uiso 1 1 calc R A .
H13B H 0.8183 0.2815 0.4918 0.039 Uiso 1 1 calc R . .
C14 C 0.8742(7) 0.3654(11) 0.3913(9) 0.036(2) Uani 1 1 d . A .
H14A H 0.9020 0.4466 0.3888 0.044 Uiso 1 1 calc R . .
H14B H 0.9178 0.2989 0.4026 0.044 Uiso 1 1 calc R . .
C15 C 0.8029(7) 0.3439(9) 0.2855(9) 0.032(2) Uani 1 1 d . . .
H15A H 0.7788 0.2590 0.2849 0.039 Uiso 1 1 calc R A .
H15B H 0.8257 0.3490 0.2255 0.039 Uiso 1 1 calc R . .
C16 C 0.7310(7) 0.4427(9) 0.2683(8) 0.0260(19) Uani 1 1 d . A .
H16A H 0.7536 0.5267 0.2614 0.031 Uiso 1 1 calc R . .
H16B H 0.6831 0.4242 0.2003 0.031 Uiso 1 1 calc R . .
C5 C 0.1566(7) 0.4072(12) 0.1463(13) 0.028(4) Uani 0.601(19) 1 d PD A 1
H5 H 0.2030 0.4376 0.2127 0.033 Uiso 0.601(19) 1 calc PR A 1
C6 C 0.0941(10) 0.5159(12) 0.0956(11) 0.038(5) Uani 0.601(19) 1 d PD A 1
H6C H 0.1263 0.5865 0.0794 0.046 Uiso 0.601(19) 1 calc PR A 1
H6D H 0.0508 0.4878 0.0268 0.046 Uiso 0.601(19) 1 calc PR A 1
C7 C 0.0487(12) 0.5603(9) 0.1737(16) 0.047(6) Uani 0.601(19) 1 d PD A 1
H7C H 0.0073 0.6274 0.1387 0.056 Uiso 0.601(19) 1 calc PR A 1
H7D H 0.0915 0.5951 0.2401 0.056 Uiso 0.601(19) 1 calc PR A 1
C8 C 0.0008(9) 0.4504(13) 0.2041(16) 0.048(6) Uani 0.601(19) 1 d PD A 1
H8C H -0.0451 0.4197 0.1385 0.058 Uiso 0.601(19) 1 calc PR A 1
H8D H -0.0263 0.4798 0.2560 0.058 Uiso 0.601(19) 1 calc PR A 1
C9 C 0.0638(11) 0.3424(13) 0.2556(13) 0.045(5) Uani 0.601(19) 1 d PD A 1
H9C H 0.0322 0.2719 0.2731 0.054 Uiso 0.601(19) 1 calc PR A 1
H9D H 0.1076 0.3715 0.3237 0.054 Uiso 0.601(19) 1 calc PR A 1
C10 C 0.1084(13) 0.2973(9) 0.1764(19) 0.044(7) Uani 0.601(19) 1 d PD A 1
H10C H 0.1494 0.2295 0.2105 0.053 Uiso 0.601(19) 1 calc PR A 1
H10D H 0.0649 0.2634 0.1100 0.053 Uiso 0.601(19) 1 calc PR A 1
C5A C 0.1275(12) 0.3998(15) 0.0949(13) 0.018(5) Uani 0.399(19) 1 d PDU A 2
H5A H 0.0793 0.4347 0.0326 0.021 Uiso 0.399(19) 1 calc PR A 2
C6A C 0.1621(9) 0.5027(14) 0.1819(14) 0.020(5) Uani 0.399(19) 1 d PDU A 2
H6A H 0.2123 0.4703 0.2416 0.024 Uiso 0.399(19) 1 calc PR A 2
H6B H 0.1810 0.5757 0.1497 0.024 Uiso 0.399(19) 1 calc PR A 2
C7A C 0.0918(12) 0.5438(13) 0.2272(17) 0.034(7) Uani 0.399(19) 1 d PD A 2
H7A H 0.0435 0.5821 0.1686 0.040 Uiso 0.399(19) 1 calc PR A 2
H7B H 0.1155 0.6075 0.2843 0.040 Uiso 0.399(19) 1 calc PR A 2
C8A C 0.0590(14) 0.4302(19) 0.2746(14) 0.037(7) Uani 0.399(19) 1 d PD A 2
H8A H 0.1064 0.3959 0.3368 0.044 Uiso 0.399(19) 1 calc PR A 2
H8B H 0.0129 0.4575 0.3010 0.044 Uiso 0.399(19) 1 calc PR A 2
C9A C 0.0245(11) 0.3274(16) 0.1876(17) 0.028(6) Uani 0.399(19) 1 d PD A 2
H9A H -0.0257 0.3598 0.1279 0.034 Uiso 0.399(19) 1 calc PR A 2
H9B H 0.0055 0.2544 0.2198 0.034 Uiso 0.399(19) 1 calc PR A 2
C10A C 0.0948(15) 0.2862(12) 0.142(2) 0.027(8) Uani 0.399(19) 1 d PD A 2
H10A H 0.0713 0.2224 0.0853 0.033 Uiso 0.399(19) 1 calc PR A 2
H10B H 0.1432 0.2481 0.2011 0.033 Uiso 0.399(19) 1 calc PR A 2


_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 N1 2.114(7) . ?
Cu1 S2 2.249(2) 2_645 ?
Cu1 S1 2.296(3) . ?
Cu1 I1 2.6287(12) . ?
Cu2 S2 2.341(2) 3_666 ?
Cu2 Cu2 2.621(2) 3_666 ?
Cu2 I1 2.6322(12) . ?
Cu2 I2 2.6359(12) . ?
Cu2 I2 2.6564(13) 3_666 ?
I2 Cu2 2.6564(13) 3_666 ?
S1 C5A 1.739(14) . ?
S1 C2 1.817(10) . ?
S1 C5 1.891(12) . ?
S2 C4 1.824(9) . ?
S2 C11 1.825(9) . ?
S2 Cu1 2.249(2) 2_655 ?
S2 Cu2 2.341(2) 3_666 ?
N1 C1 1.472(12) . ?
N1 C3 1.477(11) . ?
C1 C2 1.518(13) . ?
C3 C4 1.517(13) . ?
C11 C12 1.528(13) . ?
C11 C16 1.529(12) . ?
C12 C13 1.533(13) . ?
C13 C14 1.518(15) . ?
C14 C15 1.502(16) . ?
C15 C16 1.552(14) . ?
C5 C6 1.547(5) . ?
C5 C10 1.549(5) . ?
C6 C7 1.546(5) . ?
C7 C8 1.548(5) . ?
C8 C9 1.550(5) . ?
C9 C10 1.551(5) . ?
C5A C6A 1.548(5) . ?
C5A C10A 1.549(5) . ?
C6A C7A 1.548(5) . ?
C7A C8A 1.549(5) . ?
C8A C9A 1.548(5) . ?
C9A C10A 1.549(5) . ?

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
N1 Cu1 S2 111.7(2) . 2_645 ?
N1 Cu1 S1 90.5(2) . . ?
S2 Cu1 S1 124.15(9) 2_645 . ?
N1 Cu1 I1 108.1(2) . . ?
S2 Cu1 I1 107.82(7) 2_645 . ?
S1 Cu1 I1 112.66(8) . . ?
S2 Cu2 Cu2 128.75(8) 3_666 3_666 ?
S2 Cu2 I1 101.93(7) 3_666 . ?
Cu2 Cu2 I1 128.86(6) 3_666 . ?
S2 Cu2 I2 109.59(7) 3_666 . ?
Cu2 Cu2 I2 60.71(4) 3_666 . ?
I1 Cu2 I2 112.75(4) . . ?
S2 Cu2 I2 106.55(7) 3_666 3_666 ?
Cu2 Cu2 I2 59.93(4) 3_666 3_666 ?
I1 Cu2 I2 103.61(4) . 3_666 ?
I2 Cu2 I2 120.63(4) . 3_666 ?
Cu1 I1 Cu2 122.48(4) . . ?
Cu2 I2 Cu2 59.37(4) . 3_666 ?
C5A S1 C2 106.4(6) . . ?
C5A S1 C5 21.3(6) . . ?
C2 S1 C5 102.5(5) . . ?
C5A S1 Cu1 119.3(6) . . ?
C2 S1 Cu1 94.3(3) . . ?
C5 S1 Cu1 99.4(4) . . ?
C4 S2 C11 104.9(4) . . ?
C4 S2 Cu1 105.7(3) . 2_655 ?
C11 S2 Cu1 112.2(3) . 2_655 ?
C4 S2 Cu2 109.5(3) . 3_666 ?
C11 S2 Cu2 111.1(3) . 3_666 ?
Cu1 S2 Cu2 112.86(9) 2_655 3_666 ?
C1 N1 C3 114.8(7) . . ?
C1 N1 Cu1 104.7(5) . . ?
C3 N1 Cu1 110.5(5) . . ?
N1 C1 C2 111.4(7) . . ?
C1 C2 S1 114.3(6) . . ?
N1 C3 C4 114.5(7) . . ?
C3 C4 S2 111.8(6) . . ?
C12 C11 C16 111.6(8) . . ?
C12 C11 S2 106.2(6) . . ?
C16 C11 S2 111.8(6) . . ?
C11 C12 C13 109.8(8) . . ?
C14 C13 C12 112.3(9) . . ?
C15 C14 C13 111.3(9) . . ?
C14 C15 C16 110.6(8) . . ?
C11 C16 C15 110.7(8) . . ?
C6 C5 C10 110.5(6) . . ?
C6 C5 S1 111.6(8) . . ?
C10 C5 S1 106.2(7) . . ?
C7 C6 C5 110.7(6) . . ?
C6 C7 C8 110.7(6) . . ?
C7 C8 C9 110.4(6) . . ?
C8 C9 C10 110.2(6) . . ?
C5 C10 C9 110.3(6) . . ?
C6A C5A C10A 110.5(6) . . ?
C6A C5A S1 112.6(10) . . ?
C10A C5A S1 105.9(10) . . ?
C7A C6A C5A 110.5(6) . . ?
C6A C7A C8A 110.5(6) . . ?
C9A C8A C7A 110.5(6) . . ?
C8A C9A C10A 110.5(6) . . ?
C9A C10A C5A 110.5(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N I1 0.86(11) 3.20(10) 3.814(7) 131(8) 4_565

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         3.328
_refine_diff_density_min         -1.167
_refine_diff_density_rms         0.259
