# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1855099'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-01 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 H14 Cu2 I2 S2'
_chemical_formula_weight         651.27

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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3864(3)
_cell_length_b                   12.2916(4)
_cell_length_c                   12.5264(4)
_cell_angle_alpha                115.9720(10)
_cell_angle_beta                 106.7240(10)
_cell_angle_gamma                94.8040(10)
_cell_volume                     949.67(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9834
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      37.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    5.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4177
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_process_details   
;
The crystal's faces were indexed using Face Indexing Software. 
Bruker AXS area detector scaling and absorption correction was performed using SADABS Software
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'APEX DUO'
_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            87927
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetl/netI     0.0181
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         40.41
_reflns_number_total             11922
_reflns_number_gt                9742
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker DUO'
_computing_cell_refinement       'Bruker DUO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0369P)²+0.4989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11922
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.38167(4) 0.88514(2) 0.44294(3) 0.04048(6) Uani 1 1 d . . .
Cu2 Cu 0.11476(4) 0.98666(3) 0.60089(2) 0.03875(5) Uani 1 1 d . . .
I1 I 0.496131(16) 0.966309(11) 0.304764(12) 0.03298(3) Uani 1 1 d . . .
I2 I -0.002959(16) 0.804894(10) 0.362916(10) 0.02998(3) Uani 1 1 d . . .
S1 S 0.51061(6) 0.71090(4) 0.41484(4) 0.03022(7) Uani 1 1 d . . .
S2 S -0.01627(6) 0.90915(4) 0.71168(4) 0.02905(7) Uani 1 1 d . . .
C1 C 0.1459(5) 0.4042(3) 0.0129(3) 0.0656(8) Uani 1 1 d . . .
H1A H 0.0745 0.3418 -0.0701 0.079 Uiso 1 1 calc R . .
C2 C 0.2875(5) 0.4998(3) 0.0352(3) 0.0619(7) Uani 1 1 d . . .
H2A H 0.3098 0.5023 -0.0332 0.074 Uiso 1 1 calc R . .
C3 C 0.1103(5) 0.4008(3) 0.1132(3) 0.0587(7) Uani 1 1 d . . .
H3A H 0.0154 0.3357 0.0981 0.070 Uiso 1 1 calc R . .
C4 C 0.3972(4) 0.5927(3) 0.1583(2) 0.0465(5) Uani 1 1 d . . .
H4A H 0.4944 0.6561 0.1727 0.056 Uiso 1 1 calc R . .
C5 C 0.2155(3) 0.4943(2) 0.2371(2) 0.0427(4) Uani 1 1 d . . .
H5A H 0.1890 0.4928 0.3047 0.051 Uiso 1 1 calc R . .
C6 C 0.3604(3) 0.59007(17) 0.26008(17) 0.0310(3) Uani 1 1 d . . .
C7 C 0.4399(3) 0.66637(17) 0.52024(19) 0.0364(4) Uani 1 1 d . . .
H7A H 0.5075 0.7317 0.6076 0.044 Uiso 1 1 calc R . .
H7B H 0.3011 0.6588 0.5014 0.044 Uiso 1 1 calc R . .
C8 C 0.4837(3) 0.54919(17) 0.50777(18) 0.0346(3) Uani 1 1 d . . .
C9 C 0.3402(6) 0.6457(4) 0.7772(4) 0.0701(9) Uani 1 1 d . . .
H9A H 0.4111 0.5904 0.7895 0.084 Uiso 1 1 calc R . .
C10 C 0.4119(6) 0.7707(4) 0.8551(4) 0.0847(13) Uani 1 1 d . . .
H10A H 0.5323 0.8003 0.9210 0.102 Uiso 1 1 calc R . .
C11 C 0.1626(5) 0.6020(3) 0.6807(4) 0.0612(8) Uani 1 1 d . . .
H11A H 0.1137 0.5166 0.6262 0.073 Uiso 1 1 calc R . .
C12 C 0.3096(4) 0.8550(3) 0.8383(3) 0.0639(8) Uani 1 1 d . . .
H12A H 0.3629 0.9403 0.8905 0.077 Uiso 1 1 calc R . .
C13 C 0.0550(4) 0.6843(2) 0.6637(3) 0.0464(5) Uani 1 1 d . . .
H13A H -0.0664 0.6541 0.5986 0.056 Uiso 1 1 calc R . .
C14 C 0.1287(3) 0.81129(17) 0.74376(17) 0.0310(3) Uani 1 1 d . . .
C15 C 0.0436(3) 1.04419(19) 0.86789(17) 0.0370(4) Uani 1 1 d . . .
H15A H 0.1794 1.0868 0.8990 0.044 Uiso 1 1 calc R . .
H15B H -0.0346 1.1015 0.8593 0.044 Uiso 1 1 calc R . .
C16 C 0.0113(4) 1.0128(2) 0.96108(18) 0.0413(4) 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 S1 2.3435(5) . ?
Cu1 I1 2.6305(3) . ?
Cu1 I2 2.6599(3) . ?
Cu1 I1 2.6766(3) 2_676 ?
Cu1 Cu1 2.6966(5) 2_676 ?
Cu2 S2 2.3553(5) . ?
Cu2 I2 2.6426(3) . ?
Cu2 I2 2.6466(3) 2_576 ?
Cu2 I1 2.6758(3) 2_676 ?
Cu2 Cu2 2.7791(5) 2_576 ?
I1 Cu2 2.6758(3) 2_676 ?
I1 Cu1 2.6766(3) 2_676 ?
I2 Cu2 2.6466(3) 2_576 ?
S1 C6 1.777(2) . ?
S1 C7 1.8159(18) . ?
S2 C14 1.7737(19) . ?
S2 C15 1.8203(19) . ?
C1 C3 1.372(5) . ?
C1 C2 1.375(5) . ?
C2 C4 1.387(4) . ?
C3 C5 1.388(3) . ?
C4 C6 1.390(3) . ?
C5 C6 1.389(3) . ?
C7 C8 1.454(2) . ?
C8 C8 1.195(3) 2_666 ?
C9 C10 1.358(6) . ?
C9 C11 1.368(5) . ?
C10 C12 1.385(4) . ?
C11 C13 1.388(4) . ?
C12 C14 1.374(3) . ?
C13 C14 1.382(3) . ?
C15 C16 1.452(3) . ?
C16 C16 1.196(4) 2_577 ?

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 I1 104.657(15) . . ?
S1 Cu1 I2 106.560(15) . . ?
I1 Cu1 I2 113.809(11) . . ?
S1 Cu1 I1 105.499(16) . 2_676 ?
I1 Cu1 I1 118.931(10) . 2_676 ?
I2 Cu1 I1 106.429(11) . 2_676 ?
S1 Cu1 Cu1 120.80(2) . 2_676 ?
I1 Cu1 Cu1 60.310(11) . 2_676 ?
I2 Cu1 Cu1 132.417(17) . 2_676 ?
I1 Cu1 Cu1 58.621(11) 2_676 2_676 ?
S2 Cu2 I2 106.677(15) . . ?
S2 Cu2 I2 106.618(15) . 2_576 ?
I2 Cu2 I2 116.606(10) . 2_576 ?
S2 Cu2 I1 109.397(14) . 2_676 ?
I2 Cu2 I1 106.951(10) . 2_676 ?
I2 Cu2 I1 110.399(11) 2_576 2_676 ?
S2 Cu2 Cu2 123.04(2) . 2_576 ?
I2 Cu2 Cu2 58.372(10) . 2_576 ?
I2 Cu2 Cu2 58.234(10) 2_576 2_576 ?
I1 Cu2 Cu2 127.530(16) 2_676 2_576 ?
Cu1 I1 Cu2 104.361(9) . 2_676 ?
Cu1 I1 Cu1 61.069(10) . 2_676 ?
Cu2 I1 Cu1 71.812(9) 2_676 2_676 ?
Cu2 I2 Cu2 63.394(10) . 2_576 ?
Cu2 I2 Cu1 72.594(10) . . ?
Cu2 I2 Cu1 101.131(9) 2_576 . ?
C6 S1 C7 103.60(9) . . ?
C6 S1 Cu1 105.28(6) . . ?
C7 S1 Cu1 102.20(6) . . ?
C14 S2 C15 103.55(9) . . ?
C14 S2 Cu2 107.25(6) . . ?
C15 S2 Cu2 104.20(7) . . ?
C3 C1 C2 119.9(3) . . ?
C1 C2 C4 120.8(3) . . ?
C1 C3 C5 120.2(3) . . ?
C2 C4 C6 119.4(3) . . ?
C3 C5 C6 120.1(2) . . ?
C5 C6 C4 119.6(2) . . ?
C5 C6 S1 123.88(15) . . ?
C4 C6 S1 116.47(17) . . ?
C8 C7 S1 112.58(14) . . ?
C8 C8 C7 177.3(3) 2_666 . ?
C10 C9 C11 119.4(3) . . ?
C9 C10 C12 121.4(3) . . ?
C9 C11 C13 120.4(3) . . ?
C14 C12 C10 119.4(3) . . ?
C14 C13 C11 119.8(3) . . ?
C12 C14 C13 119.6(2) . . ?
C12 C14 S2 123.84(18) . . ?
C13 C14 S2 116.52(16) . . ?
C16 C15 S2 113.50(16) . . ?
C16 C16 C15 178.6(3) 2_577 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 Cu1 I1 Cu2 -58.039(17) . . . 2_676 ?
I2 Cu1 I1 Cu2 -173.978(10) . . . 2_676 ?
I1 Cu1 I1 Cu2 59.359(14) 2_676 . . 2_676 ?
Cu1 Cu1 I1 Cu2 59.359(14) 2_676 . . 2_676 ?
S1 Cu1 I1 Cu1 -117.40(2) . . . 2_676 ?
I2 Cu1 I1 Cu1 126.663(18) . . . 2_676 ?
I1 Cu1 I1 Cu1 0.0 2_676 . . 2_676 ?
S2 Cu2 I2 Cu2 118.94(2) . . . 2_576 ?
I2 Cu2 I2 Cu2 0.0 2_576 . . 2_576 ?
I1 Cu2 I2 Cu2 -124.070(16) 2_676 . . 2_576 ?
S2 Cu2 I2 Cu1 -128.516(16) . . . . ?
I2 Cu2 I2 Cu1 112.539(13) 2_576 . . . ?
I1 Cu2 I2 Cu1 -11.531(10) 2_676 . . . ?
Cu2 Cu2 I2 Cu1 112.539(13) 2_576 . . . ?
S1 Cu1 I2 Cu2 123.726(17) . . . . ?
I1 Cu1 I2 Cu2 -121.455(13) . . . . ?
I1 Cu1 I2 Cu2 11.496(9) 2_676 . . . ?
Cu1 Cu1 I2 Cu2 -50.74(2) 2_676 . . . ?
S1 Cu1 I2 Cu2 -178.959(15) . . . 2_576 ?
I1 Cu1 I2 Cu2 -64.141(13) . . . 2_576 ?
I1 Cu1 I2 Cu2 68.810(11) 2_676 . . 2_576 ?
Cu1 Cu1 I2 Cu2 6.58(3) 2_676 . . 2_576 ?
I1 Cu1 S1 C6 -75.59(6) . . . . ?
I2 Cu1 S1 C6 45.28(6) . . . . ?
I1 Cu1 S1 C6 158.15(6) 2_676 . . . ?
Cu1 Cu1 S1 C6 -139.48(6) 2_676 . . . ?
I1 Cu1 S1 C7 176.45(8) . . . . ?
I2 Cu1 S1 C7 -62.68(8) . . . . ?
I1 Cu1 S1 C7 50.19(8) 2_676 . . . ?
Cu1 Cu1 S1 C7 112.56(8) 2_676 . . . ?
I2 Cu2 S2 C14 77.72(7) . . . . ?
I2 Cu2 S2 C14 -157.02(7) 2_576 . . . ?
I1 Cu2 S2 C14 -37.63(7) 2_676 . . . ?
Cu2 Cu2 S2 C14 140.45(7) 2_576 . . . ?
I2 Cu2 S2 C15 -172.92(7) . . . . ?
I2 Cu2 S2 C15 -47.66(8) 2_576 . . . ?
I1 Cu2 S2 C15 71.73(8) 2_676 . . . ?
Cu2 Cu2 S2 C15 -110.19(8) 2_576 . . . ?
C3 C1 C2 C4 0.8(5) . . . . ?
C2 C1 C3 C5 0.6(5) . . . . ?
C1 C2 C4 C6 -1.3(4) . . . . ?
C1 C3 C5 C6 -1.5(5) . . . . ?
C3 C5 C6 C4 1.0(4) . . . . ?
C3 C5 C6 S1 -177.4(2) . . . . ?
C2 C4 C6 C5 0.4(4) . . . . ?
C2 C4 C6 S1 178.9(2) . . . . ?
C7 S1 C6 C5 4.9(2) . . . . ?
Cu1 S1 C6 C5 -102.08(17) . . . . ?
C7 S1 C6 C4 -173.55(16) . . . . ?
Cu1 S1 C6 C4 79.51(16) . . . . ?
C6 S1 C7 C8 63.67(18) . . . . ?
Cu1 S1 C7 C8 172.92(15) . . . . ?
S1 C7 C8 C8 -48(6) . . . 2_666 ?
C11 C9 C10 C12 -0.4(7) . . . . ?
C10 C9 C11 C13 -1.1(5) . . . . ?
C9 C10 C12 C14 2.3(7) . . . . ?
C9 C11 C13 C14 0.8(4) . . . . ?
C10 C12 C14 C13 -2.6(5) . . . . ?
C10 C12 C14 S2 -179.5(3) . . . . ?
C11 C13 C14 C12 1.1(4) . . . . ?
C11 C13 C14 S2 178.2(2) . . . . ?
C15 S2 C14 C12 -32.9(3) . . . . ?
Cu2 S2 C14 C12 76.9(2) . . . . ?
C15 S2 C14 C13 150.06(16) . . . . ?
Cu2 S2 C14 C13 -100.12(16) . . . . ?
C14 S2 C15 C16 -56.14(18) . . . . ?
Cu2 S2 C15 C16 -168.20(15) . . . . ?
S2 C15 C16 C16 101(14) . . . 2_577 ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        40.41
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.812
_refine_diff_density_min         -2.127
_refine_diff_density_rms         0.211
