# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_sd
_database_code_depnum_ccdc_archive 'CCDC 1446192'
_audit_update_record             
;
2016-01-08 deposited with the CCDC.
2017-04-25 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 H26 Cl2 Cu N6 O8 S2'
_chemical_formula_weight         629.02

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   13.9357(3)
_cell_length_b                   6.68730(10)
_cell_length_c                   27.1213(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.3250(10)
_cell_angle_gamma                90.00
_cell_volume                     2525.41(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1292
_exptl_absorpt_coefficient_mu    1.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  2.87
_exptl_absorpt_correction_T_max  2.99
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20108
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         27.53
_reflns_number_total             2890
_reflns_number_gt                2542
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0445P)²+2.2970P] 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         2890
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_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 0.0000 1.13705(5) 0.2500 0.04054(12) Uani 1 2 d S . .
Cl1 Cl -0.11864(6) 1.35195(9) 0.26242(3) 0.0692(2) Uani 1 1 d . . .
S1 S -0.00325(3) 0.21962(7) 0.058256(16) 0.03409(13) Uani 1 1 d . . .
O1 O -0.07541(11) 0.3186(2) 0.02773(5) 0.0470(4) Uani 1 1 d . . .
O2 O -0.02053(11) 0.0163(2) 0.07321(5) 0.0459(3) Uani 1 1 d . . .
O3 O 0.29870(11) 0.7844(4) 0.13941(8) 0.0741(6) Uani 1 1 d . . .
O4 O 0.21518(11) 0.5531(3) 0.10261(7) 0.0607(5) Uani 1 1 d . . .
C444 C 0.01731(13) 0.3622(3) 0.11309(6) 0.0308(4) Uani 1 1 d . . .
H44A H -0.0306 0.3283 0.1367 0.037 Uiso 1 1 calc R . .
H44B H 0.0801 0.3299 0.1277 0.037 Uiso 1 1 calc R . .
N2 N 0.22299(12) 0.6966(3) 0.13031(7) 0.0458(4) Uani 1 1 d . . .
N200 N 0.04700(12) 0.9329(2) 0.20284(6) 0.0355(3) Uani 1 1 d . . .
C2 C -0.00683(13) 0.8101(3) 0.17426(6) 0.0303(4) Uani 1 1 d . . .
N100 N 0.04808(10) 0.7074(2) 0.14340(5) 0.0293(3) Uani 1 1 d . . .
C4 C 0.01219(13) 0.5845(3) 0.10165(6) 0.0310(4) Uani 1 1 d . . .
H4A H 0.0498 0.6124 0.0731 0.037 Uiso 1 1 calc R . .
H4B H -0.0539 0.6208 0.0934 0.037 Uiso 1 1 calc R . .
C5 C 0.10609(16) 0.2273(3) 0.02709(7) 0.0435(5) Uani 1 1 d . . .
H5A H 0.0940 0.1844 -0.0068 0.052 Uiso 1 1 calc R . .
H5B H 0.1286 0.3645 0.0263 0.052 Uiso 1 1 calc R . .
C6 C 0.18462(19) 0.0975(4) 0.05053(10) 0.0647(7) Uani 1 1 d . . .
H6A H 0.1974 0.1393 0.0840 0.097 Uiso 1 1 calc R . .
H6B H 0.2419 0.1106 0.0323 0.097 Uiso 1 1 calc R . .
H6C H 0.1642 -0.0396 0.0501 0.097 Uiso 1 1 calc R . .
C7 C 0.14115(13) 0.7699(3) 0.15362(7) 0.0352(4) Uani 1 1 d . . .
C8 C 0.13982(14) 0.9075(3) 0.19006(7) 0.0402(4) Uani 1 1 d . . .
H8 H 0.1930 0.9736 0.2040 0.048 Uiso 1 1 calc R . .
C9 C -0.11250(14) 0.7919(3) 0.17534(8) 0.0427(5) Uani 1 1 d . . .
H9A H -0.1361 0.8794 0.2002 0.064 Uiso 1 1 calc R . .
H9B H -0.1293 0.6564 0.1828 0.064 Uiso 1 1 calc R . .
H9C H -0.1407 0.8282 0.1437 0.064 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0691(3) 0.02493(18) 0.02714(17) 0.000 -0.00387(15) 0.000
Cl1 0.1059(5) 0.0429(3) 0.0574(4) -0.0014(3) -0.0146(3) 0.0315(3)
S1 0.0471(3) 0.0246(2) 0.0301(2) -0.00005(16) -0.00234(18) -0.00276(18)
O1 0.0552(9) 0.0415(8) 0.0429(8) 0.0015(6) -0.0153(7) -0.0019(7)
O2 0.0682(9) 0.0248(7) 0.0446(8) 0.0004(6) 0.0026(7) -0.0065(6)
O3 0.0364(8) 0.1022(16) 0.0840(14) -0.0244(12) 0.0055(8) -0.0182(9)
O4 0.0474(9) 0.0618(11) 0.0734(11) -0.0207(9) 0.0099(8) 0.0013(8)
C444 0.0381(9) 0.0267(9) 0.0274(8) -0.0001(6) 0.0006(7) -0.0023(7)
N2 0.0372(9) 0.0544(11) 0.0457(10) 0.0002(9) 0.0011(7) -0.0028(8)
N200 0.0461(9) 0.0307(8) 0.0295(7) -0.0011(6) -0.0001(6) -0.0080(7)
C2 0.0383(9) 0.0243(8) 0.0283(8) 0.0016(6) 0.0003(7) -0.0017(7)
N100 0.0335(7) 0.0257(7) 0.0285(7) -0.0001(6) -0.0020(6) -0.0015(6)
C4 0.0375(9) 0.0268(8) 0.0284(8) -0.0025(7) -0.0039(7) 0.0013(7)
C5 0.0597(13) 0.0375(11) 0.0341(10) 0.0017(8) 0.0113(9) 0.0010(9)
C6 0.0618(15) 0.0656(17) 0.0680(17) 0.0135(13) 0.0196(13) 0.0168(13)
C7 0.0350(9) 0.0366(10) 0.0337(9) 0.0008(7) -0.0008(7) -0.0061(8)
C8 0.0431(10) 0.0422(11) 0.0349(9) -0.0024(8) -0.0033(8) -0.0137(9)
C9 0.0380(10) 0.0449(12) 0.0452(11) -0.0064(9) 0.0027(8) -0.0011(9)

_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 N200 1.9993(16) 2 ?
Cu1 N200 1.9993(16) . ?
Cu1 Cl1 2.2265(7) 2 ?
Cu1 Cl1 2.2265(7) . ?
S1 O1 1.4378(15) . ?
S1 O2 1.4418(14) . ?
S1 C5 1.773(2) . ?
S1 C444 1.7798(18) . ?
O3 N2 1.224(2) . ?
O4 N2 1.221(2) . ?
C444 C4 1.520(2) . ?
C444 H44A 0.9700 . ?
C444 H44B 0.9700 . ?
N2 C7 1.414(3) . ?
N200 C2 1.338(2) . ?
N200 C8 1.363(3) . ?
C2 N100 1.345(2) . ?
C2 C9 1.479(3) . ?
N100 C7 1.380(2) . ?
N100 C4 1.470(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.516(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.351(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
N200 Cu1 N200 93.85(9) 2 . ?
N200 Cu1 Cl1 143.33(5) 2 2 ?
N200 Cu1 Cl1 94.56(5) . 2 ?
N200 Cu1 Cl1 94.56(5) 2 . ?
N200 Cu1 Cl1 143.33(5) . . ?
Cl1 Cu1 Cl1 99.60(4) 2 . ?
O1 S1 O2 118.38(9) . . ?
O1 S1 C5 107.86(10) . . ?
O2 S1 C5 108.55(10) . . ?
O1 S1 C444 108.63(9) . . ?
O2 S1 C444 107.05(8) . . ?
C5 S1 C444 105.69(9) . . ?
C4 C444 S1 110.42(12) . . ?
C4 C444 H44A 109.6 . . ?
S1 C444 H44A 109.6 . . ?
C4 C444 H44B 109.6 . . ?
S1 C444 H44B 109.6 . . ?
H44A C444 H44B 108.1 . . ?
O4 N2 O3 123.77(19) . . ?
O4 N2 C7 119.62(17) . . ?
O3 N2 C7 116.60(19) . . ?
C2 N200 C8 106.97(16) . . ?
C2 N200 Cu1 126.80(13) . . ?
C8 N200 Cu1 125.90(13) . . ?
N200 C2 N100 110.73(16) . . ?
N200 C2 C9 125.05(17) . . ?
N100 C2 C9 124.21(16) . . ?
C2 N100 C7 105.92(15) . . ?
C2 N100 C4 125.47(15) . . ?
C7 N100 C4 127.70(15) . . ?
N100 C4 C444 112.22(14) . . ?
N100 C4 H4A 109.2 . . ?
C444 C4 H4A 109.2 . . ?
N100 C4 H4B 109.2 . . ?
C444 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 S1 113.77(15) . . ?
C6 C5 H5A 108.8 . . ?
S1 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
S1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N100 108.20(17) . . ?
C8 C7 N2 126.77(18) . . ?
N100 C7 N2 125.01(17) . . ?
C7 C8 N200 108.18(17) . . ?
C7 C8 H8 125.9 . . ?
N200 C8 H8 125.9 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.064
