# 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_cucldmpztzd
_database_code_depnum_ccdc_archive 'CCDC 1532496'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;

_audit_creation_date             2017-06-29T20:42:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H26 Cl4 Cu2 N6 S2'
_chemical_formula_sum            'C18 H26 Cl4 Cu2 N6 S2'
_chemical_formula_weight         659.45
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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                   17.3533(6)
_cell_length_b                   9.0977(3)
_cell_length_c                   17.7828(6)
_cell_angle_alpha                90
_cell_angle_beta                 118.7020(10)
_cell_angle_gamma                90
_cell_volume                     2462.51(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4431
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.375
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_T_max  0.7047
_shelx_estimated_absorpt_T_min   0.602
_shelx_estimated_absorpt_T_max   0.705

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker X8 KappaAPEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_standards_number         '50 first frames'
_diffrn_standards_interval_time  'set of frames'
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_number            2532
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.608
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_full        0.5
_diffrn_measured_fraction_theta_full 0
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             2532
_reflns_number_gt                2228
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX2'
_computing_cell_refinement       'BRUKER APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0203P)²+4.3665P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2532
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0536
_refine_ls_wR_factor_gt          0.0517
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.077

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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'

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 0.11547(13) 0.3022(2) 1.13802(13) 0.0108(4) Uani 1 1 d . . . . .
C2 C 0.15361(15) 0.0458(2) 1.14566(13) 0.0137(4) Uani 1 1 d . . . . .
H2A H 0.201 -0.0013 1.1383 0.016 Uiso 1 1 calc R U . . .
H2B H 0.0999 -0.0142 1.1141 0.016 Uiso 1 1 calc R U . . .
C3 C 0.17952(15) 0.0445(2) 1.24019(14) 0.0167(5) Uani 1 1 d . . . . .
H3A H 0.1892 -0.058 1.2614 0.02 Uiso 1 1 calc R U . . .
H3B H 0.2351 0.0994 1.2731 0.02 Uiso 1 1 calc R U . . .
C4 C 0.10790(15) 0.1143(2) 1.25373(14) 0.0179(5) Uani 1 1 d . . . . .
H4A H 0.1226 0.1038 1.3146 0.022 Uiso 1 1 calc R U . . .
H4B H 0.0516 0.0627 1.2182 0.022 Uiso 1 1 calc R U . . .
C5 C 0.13031(14) 0.5760(2) 1.00912(13) 0.0124(4) Uani 1 1 d . . . . .
C6 C 0.09746(14) 0.6656(2) 1.05175(13) 0.0149(4) Uani 1 1 d . . . . .
H6 H 0.0861 0.7681 1.0433 0.018 Uiso 1 1 calc R U . . .
C7 C 0.08484(14) 0.5789(2) 1.10736(13) 0.0135(4) Uani 1 1 d . . . . .
C8 C 0.15776(15) 0.6236(2) 0.94535(14) 0.0184(5) Uani 1 1 d . . . . .
H8A H 0.2185 0.5927 0.9647 0.028 Uiso 1 1 calc R U . . .
H8B H 0.1537 0.7308 0.9398 0.028 Uiso 1 1 calc R U . . .
H8C H 0.1191 0.5785 0.8897 0.028 Uiso 1 1 calc R U . . .
C9 C 0.05313(15) 0.6257(2) 1.16844(14) 0.0182(5) Uani 1 1 d . . . . .
H9A H 0.0363 0.7296 1.159 0.027 Uiso 1 1 calc R U . . .
H9B H 0.1002 0.612 1.2275 0.027 Uiso 1 1 calc R U . . .
H9C H 0.0022 0.5661 1.1589 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 0.17953(3) 0.28597(6) 0.89452(3) 0.01287(12) Uani 1 1 d . . . . .
Cl2 Cl 0.08799(4) 0.01445(6) 0.94378(3) 0.01527(12) Uani 1 1 d . . . . .
Cu1 Cu 0.15329(2) 0.23000(3) 1.00474(2) 0.00950(8) Uani 1 1 d . . . . .
N1 N 0.13720(11) 0.19323(18) 1.10708(11) 0.0104(4) Uani 1 1 d . . . . .
N2 N 0.10877(11) 0.43865(18) 1.09704(10) 0.0103(4) Uani 1 1 d . . . . .
N3 N 0.13624(11) 0.43756(19) 1.03580(10) 0.0111(4) Uani 1 1 d . . . . .
S S 0.09555(4) 0.30740(6) 1.22520(4) 0.01855(13) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.276(3) . ?
C1 N2 1.415(3) . ?
C1 S 1.744(2) . ?
C2 N1 1.470(3) . ?
C2 C3 1.517(3) . ?
C3 C4 1.514(3) . ?
C4 S 1.813(2) . ?
C5 N3 1.332(3) . ?
C5 C6 1.407(3) . ?
C5 C8 1.490(3) . ?
C6 C7 1.362(3) . ?
C7 N2 1.381(3) . ?
C7 C9 1.496(3) . ?
Cl1 Cu1 2.2727(5) . ?
Cl1 Cu1 2.5798(6) 7_557 ?
Cl2 Cu1 2.2639(6) . ?
Cu1 N1 1.9975(16) . ?
Cu1 N3 2.0286(17) . ?
Cu1 Cl1 2.5797(6) 7_557 ?
N2 N3 1.383(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
N1 C1 N2 115.32(17) . . ?
N1 C1 S 129.07(16) . . ?
N2 C1 S 115.59(14) . . ?
N1 C2 C3 114.35(17) . . ?
C4 C3 C2 110.09(18) . . ?
C3 C4 S 110.96(15) . . ?
N3 C5 C6 109.74(18) . . ?
N3 C5 C8 123.20(19) . . ?
C6 C5 C8 127.04(19) . . ?
C7 C6 C5 107.68(19) . . ?
C6 C7 N2 105.97(17) . . ?
C6 C7 C9 127.3(2) . . ?
N2 C7 C9 126.76(19) . . ?
Cu1 Cl1 Cu1 90.730(18) . 7_557 ?
N1 Cu1 N3 78.78(7) . . ?
N1 Cu1 Cl2 91.97(5) . . ?
N3 Cu1 Cl2 146.28(5) . . ?
N1 Cu1 Cl1 175.41(5) . . ?
N3 Cu1 Cl1 98.17(5) . . ?
Cl2 Cu1 Cl1 92.44(2) . . ?
N1 Cu1 Cl1 87.74(5) . 7_557 ?
N3 Cu1 Cl1 97.23(5) . 7_557 ?
Cl2 Cu1 Cl1 114.90(2) . 7_557 ?
Cl1 Cu1 Cl1 89.269(18) . 7_557 ?
C1 N1 C2 122.60(17) . . ?
C1 N1 Cu1 117.54(14) . . ?
C2 N1 Cu1 119.82(12) . . ?
C7 N2 N3 110.53(16) . . ?
C7 N2 C1 134.21(17) . . ?
N3 N2 C1 115.15(16) . . ?
C5 N3 N2 106.06(16) . . ?
C5 N3 Cu1 141.21(14) . . ?
N2 N3 Cu1 111.82(12) . . ?
C1 S C4 100.10(10) . . ?

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cucldmpztzm
_database_code_depnum_ccdc_archive 'CCDC 1532497'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;

_audit_creation_date             2017-06-29T20:52:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H13 Cl2 Cu1 N3 S1'
_chemical_formula_sum            'C9 H13 Cl2 Cu N3 S'
_chemical_formula_weight         329.72
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'


_cell_length_a                   7.5613(3)
_cell_length_b                   17.6501(7)
_cell_length_c                   18.5075(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2469.97(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1792
_cell_measurement_theta_min      3.131
_cell_measurement_theta_max      26.3425
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.35
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.3991
_exptl_absorpt_correction_T_max  0.4942
_shelx_estimated_absorpt_T_min   0.399
_shelx_estimated_absorpt_T_max   0.494

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker X8 KappaAPEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.014
_diffrn_reflns_number            2533
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_full        0.5
_diffrn_measured_fraction_theta_full 0
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 0
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             2533
_reflns_number_gt                2367
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX2'
_computing_cell_refinement       'BRUKER APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0255P)²+1.6620P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2533
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0545
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.085

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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'

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 0.1986(2) 0.65152(10) 0.34455(9) 0.0111(3) Uani 1 1 d . . . . .
C2 C 0.1800(3) 0.66349(10) 0.47437(9) 0.0146(4) Uani 1 1 d . . . . .
H2A H 0.0875 0.6874 0.5046 0.018 Uiso 1 1 calc R U . . .
H2B H 0.2964 0.6786 0.4941 0.018 Uiso 1 1 calc R U . . .
C3 C 0.1620(3) 0.57828(10) 0.47994(10) 0.0163(4) Uani 1 1 d . . . . .
H3A H 0.1716 0.5627 0.5312 0.02 Uiso 1 1 calc R U . . .
H3B H 0.0443 0.5626 0.4619 0.02 Uiso 1 1 calc R U . . .
C4 C 0.3048(3) 0.53972(11) 0.43617(10) 0.0190(4) Uani 1 1 d . . . . .
H4A H 0.2998 0.4844 0.4446 0.023 Uiso 1 1 calc R U . . .
H4B H 0.4222 0.5581 0.4521 0.023 Uiso 1 1 calc R U . . .
C5 C 0.0757(2) 0.78140(10) 0.21200(9) 0.0127(4) Uani 1 1 d . . . . .
C6 C 0.1276(2) 0.72304(10) 0.16502(10) 0.0154(4) Uani 1 1 d . . . . .
H6 H 0.1235 0.7246 0.1137 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1849(2) 0.66368(10) 0.20613(9) 0.0130(3) Uani 1 1 d . . . . .
C8 C 0.0045(2) 0.85720(10) 0.19171(9) 0.0158(4) Uani 1 1 d . . . . .
H8A H -0.1111 0.8646 0.2146 0.024 Uiso 1 1 calc R U . . .
H8B H -0.0084 0.8601 0.1391 0.024 Uiso 1 1 calc R U . . .
H8C H 0.0862 0.8967 0.2081 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2520(2) 0.58909(10) 0.17999(10) 0.0169(4) Uani 1 1 d . . . . .
H9A H 0.2557 0.5891 0.1271 0.025 Uiso 1 1 calc R U . . .
H9B H 0.1732 0.5487 0.1967 0.025 Uiso 1 1 calc R U . . .
H9C H 0.3713 0.5805 0.199 0.025 Uiso 1 1 calc R U . . .
Cl1 Cl 0.21375(6) 0.84192(2) 0.48403(2) 0.01551(11) Uani 1 1 d . . . . .
Cl2 Cl -0.06504(6) 0.90131(2) 0.36114(2) 0.01701(11) Uani 1 1 d . . . . .
Cu Cu 0.09577(3) 0.79931(2) 0.38089(2) 0.00958(7) Uani 1 1 d . . . . .
N1 N 0.1643(2) 0.69258(8) 0.39983(8) 0.0110(3) Uani 1 1 d . . . . .
N2 N 0.16728(19) 0.68669(8) 0.27678(8) 0.0111(3) Uani 1 1 d . . . . .
N3 N 0.10003(18) 0.75940(8) 0.28020(8) 0.0111(3) Uani 1 1 d . . . . .
S S 0.27713(6) 0.55891(2) 0.34056(2) 0.01471(11) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.280(2) . ?
C1 N2 1.419(2) . ?
C1 S 1.7408(17) . ?
C2 N1 1.477(2) . ?
C2 C3 1.514(2) . ?
C3 C4 1.511(3) . ?
C4 S 1.8137(19) . ?
C5 N3 1.333(2) . ?
C5 C6 1.404(3) . ?
C5 C8 1.490(2) . ?
C6 C7 1.366(3) . ?
C7 N2 1.376(2) . ?
C7 C9 1.491(2) . ?
Cl1 Cu 2.2372(5) . ?
Cl2 Cu 2.2029(5) . ?
Cu N1 1.9851(14) . ?
Cu N3 1.9925(15) . ?
N2 N3 1.382(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
N1 C1 N2 115.15(15) . . ?
N1 C1 S 129.38(14) . . ?
N2 C1 S 115.47(12) . . ?
N1 C2 C3 113.70(14) . . ?
C4 C3 C2 110.30(15) . . ?
C3 C4 S 110.89(13) . . ?
N3 C5 C6 109.52(16) . . ?
N3 C5 C8 123.35(16) . . ?
C6 C5 C8 127.13(16) . . ?
C7 C6 C5 107.85(16) . . ?
C6 C7 N2 105.80(15) . . ?
C6 C7 C9 127.19(16) . . ?
N2 C7 C9 127.01(16) . . ?
N1 Cu N3 79.95(6) . . ?
N1 Cu Cl2 161.62(5) . . ?
N3 Cu Cl2 98.20(4) . . ?
N1 Cu Cl1 93.68(4) . . ?
N3 Cu Cl1 155.56(4) . . ?
Cl2 Cu Cl1 94.988(18) . . ?
C1 N1 C2 122.24(15) . . ?
C1 N1 Cu 116.67(12) . . ?
C2 N1 Cu 121.06(11) . . ?
C7 N2 N3 110.70(14) . . ?
C7 N2 C1 134.00(15) . . ?
N3 N2 C1 115.28(13) . . ?
C5 N3 N2 106.13(14) . . ?
C5 N3 Cu 141.28(13) . . ?
N2 N3 Cu 112.16(10) . . ?
C1 S C4 99.98(8) . . ?

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cupztz
_database_code_depnum_ccdc_archive 'CCDC 1532498'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;

_audit_creation_date             2017-06-29T20:20:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H18 Cl4 Cu2 N6 S2'
_chemical_formula_sum            'C14 H18 Cl4 Cu2 N6 S2'
_chemical_formula_weight         603.34
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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                   17.2598(14)
_cell_length_b                   8.9759(7)
_cell_length_c                   14.2902(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.6000(10)
_cell_angle_gamma                90
_cell_volume                     2121.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12014
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.2
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.889
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.4959
_exptl_absorpt_correction_T_max  0.5614
_shelx_estimated_absorpt_T_min   0.496
_shelx_estimated_absorpt_T_max   0.561

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_number            12014
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.463
_diffrn_reflns_theta_max         28.221
_diffrn_reflns_theta_full        0.5
_diffrn_measured_fraction_theta_full 0
_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0
_diffrn_reflns_point_group_measured_fraction_max 0.951
_reflns_Friedel_coverage         0
_reflns_number_total             2482
_reflns_number_gt                2300
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0420P)²+7.4127P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2482
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.422
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.085

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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'

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 0.21618(19) -0.1301(4) 0.1353(2) 0.0345(6) Uani 1 1 d . . . . .
C2 C 0.0922(2) -0.0194(4) 0.1382(3) 0.0460(8) Uani 1 1 d . . . . .
H2A H 0.0625 0.0671 0.1063 0.055 Uiso 1 1 calc R U . . .
H2B H 0.0935 -0.0162 0.2065 0.055 Uiso 1 1 calc R U . . .
C3 C 0.0494(2) -0.1549(5) 0.0935(4) 0.0632(12) Uani 1 1 d . . . . .
H3A H 0.0471 -0.1557 0.0249 0.076 Uiso 1 1 calc R U . . .
H3B H -0.0057 -0.1498 0.0974 0.076 Uiso 1 1 calc R U . . .
C4 C 0.0859(2) -0.2984(4) 0.1382(4) 0.0558(11) Uani 1 1 d . . . . .
H4A H 0.0563 -0.3803 0.0999 0.067 Uiso 1 1 calc R U . . .
H4B H 0.0798 -0.306 0.2034 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3947(2) 0.0177(4) 0.1163(3) 0.0435(8) Uani 1 1 d . . . . .
H5 H 0.4265 0.0983 0.1095 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4207(2) -0.1297(4) 0.1249(3) 0.0455(8) Uani 1 1 d . . . . .
H6 H 0.4715 -0.1652 0.1254 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3561(2) -0.2111(4) 0.1325(3) 0.0436(8) Uani 1 1 d . . . . .
H7 H 0.3541 -0.314 0.1392 0.052 Uiso 1 1 calc R U . . .
Cl1 Cl 0.31967(5) 0.36515(9) 0.09425(7) 0.0414(2) Uani 1 1 d . . . . .
Cl2 Cl 0.13455(5) 0.33174(9) 0.12143(7) 0.0446(2) Uani 1 1 d . . . . .
Cu Cu 0.23250(2) 0.17916(4) 0.10771(3) 0.03388(14) Uani 1 1 d . . . . .
N1 N 0.17534(16) -0.0116(3) 0.1311(2) 0.0348(6) Uani 1 1 d . . . . .
N2 N 0.29514(15) -0.1129(3) 0.1282(2) 0.0348(6) Uani 1 1 d . . . . .
N3 N 0.31899(16) 0.0282(3) 0.1190(2) 0.0372(6) Uani 1 1 d . . . . .
S S 0.19195(5) -0.31671(9) 0.14552(8) 0.0446(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.268(4) . ?
C1 N2 1.404(4) . ?
C1 S 1.743(3) . ?
C2 N1 1.469(4) . ?
C2 C3 1.470(5) . ?
C3 C4 1.494(6) . ?
C4 S 1.811(4) . ?
C5 N3 1.322(4) . ?
C5 C6 1.391(5) . ?
C6 C7 1.363(5) . ?
C7 N2 1.361(4) . ?
Cl1 Cu 2.2919(8) . ?
Cl2 Cu 2.2274(8) . ?
Cu N3 1.988(3) . ?
Cu N1 2.050(3) . ?
N2 N3 1.349(4) . ?

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 C1 N2 116.2(3) . . ?
N1 C1 S 131.8(2) . . ?
N2 C1 S 111.9(2) . . ?
N1 C2 C3 112.9(3) . . ?
C2 C3 C4 115.4(4) . . ?
C3 C4 S 113.5(3) . . ?
N3 C5 C6 111.2(3) . . ?
C7 C6 C5 105.5(3) . . ?
N2 C7 C6 106.8(3) . . ?
N3 Cu N1 78.63(11) . . ?
N3 Cu Cl2 169.44(9) . . ?
N1 Cu Cl2 94.95(8) . . ?
N3 Cu Cl1 90.43(8) . . ?
N1 Cu Cl1 168.46(8) . . ?
Cl2 Cu Cl1 95.30(3) . . ?
C1 N1 C2 119.8(3) . . ?
C1 N1 Cu 114.9(2) . . ?
C2 N1 Cu 125.2(2) . . ?
N3 N2 C7 111.1(3) . . ?
N3 N2 C1 116.1(2) . . ?
C7 N2 C1 132.8(3) . . ?
C5 N3 N2 105.5(3) . . ?
C5 N3 Cu 140.5(2) . . ?
N2 N3 Cu 113.87(19) . . ?
C1 S C4 99.83(16) . . ?

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cucldphpztz
_database_code_depnum_ccdc_archive 'CCDC 1532499'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;

_audit_creation_date             2017-06-29T21:04:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C38 H34 Cl4 Cu2 N6 S2'
_chemical_formula_sum            'C38 H34 Cl4 Cu2 N6 S2'
_chemical_formula_weight         907.71
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   6.340(5)
_cell_length_b                   15.756(5)
_cell_length_c                   19.015(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 98.637(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1877.9(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1970
_cell_measurement_theta_min      2.523
_cell_measurement_theta_max      24.9185
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.6593
_exptl_absorpt_correction_T_max  0.9545
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.955

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_number            3829
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.686
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_full        0.5
_diffrn_measured_fraction_theta_full 0
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3829
_reflns_number_gt                3100
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX2'
_computing_cell_refinement       'BRUKER APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0815P)²+2.3929P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3829
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.138
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.433
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.151

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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'

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 0.9556(6) 0.5086(2) 0.1609(2) 0.0141(8) Uani 1 1 d . . . . .
C2 C 0.8159(7) 0.3888(3) 0.0913(2) 0.0198(9) Uani 1 1 d . . . . .
H2A H 0.9266 0.3677 0.0641 0.024 Uiso 1 1 calc R U . . .
H2B H 0.6753 0.3799 0.0618 0.024 Uiso 1 1 calc R U . . .
C3 C 0.8254(8) 0.3378(3) 0.1587(3) 0.0264(10) Uani 1 1 d . . . . .
H3A H 0.798 0.2773 0.1466 0.032 Uiso 1 1 calc R U . . .
H3B H 0.7126 0.3576 0.1856 0.032 Uiso 1 1 calc R U . . .
C4 C 1.0417(8) 0.3463(3) 0.2050(2) 0.0258(10) Uani 1 1 d . . . . .
H4A H 1.1551 0.3282 0.1777 0.031 Uiso 1 1 calc R U . . .
H4B H 1.0473 0.3087 0.247 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7867(6) 0.7183(3) 0.1463(2) 0.0152(8) Uani 1 1 d . . . . .
C6 C 0.9523(6) 0.7307(3) 0.2045(2) 0.0158(8) Uani 1 1 d . . . . .
H6 H 0.9856 0.7822 0.2298 0.019 Uiso 1 1 calc R U . . .
C7 C 1.0547(6) 0.6548(3) 0.2171(2) 0.0151(8) Uani 1 1 d . . . . .
C8 C 0.6194(6) 0.7786(3) 0.1167(2) 0.0157(8) Uani 1 1 d . . . . .
C9 C 0.4150(6) 0.7496(3) 0.0916(2) 0.0156(8) Uani 1 1 d . . . . .
H9 H 0.3859 0.6904 0.0911 0.019 Uiso 1 1 calc R U . . .
C10 C 0.2528(6) 0.8063(3) 0.0672(2) 0.0188(9) Uani 1 1 d . . . . .
H10 H 0.1136 0.7859 0.0499 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2941(7) 0.8924(3) 0.0680(2) 0.0224(10) Uani 1 1 d . . . . .
H11 H 0.1829 0.9314 0.052 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4993(7) 0.9220(3) 0.0924(2) 0.0227(10) Uani 1 1 d . . . . .
H12 H 0.5281 0.9812 0.0923 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6606(7) 0.8658(3) 0.1168(2) 0.0195(9) Uani 1 1 d . . . . .
H13 H 0.7999 0.8863 0.1336 0.023 Uiso 1 1 calc R U . . .
C14 C 1.2396(6) 0.6339(2) 0.2716(2) 0.0150(8) Uani 1 1 d . . . . .
C15 C 1.2248(7) 0.6490(3) 0.3428(2) 0.0177(9) Uani 1 1 d . . . . .
H15 H 1.0966 0.6714 0.3556 0.021 Uiso 1 1 calc R U . . .
C16 C 1.3952(7) 0.6318(3) 0.3951(2) 0.0207(9) Uani 1 1 d . . . . .
H16 H 1.3842 0.6422 0.4436 0.025 Uiso 1 1 calc R U . . .
C17 C 1.5825(7) 0.5991(3) 0.3765(2) 0.0216(9) Uani 1 1 d . . . . .
H17 H 1.6994 0.5866 0.4125 0.026 Uiso 1 1 calc R U . . .
C18 C 1.5995(7) 0.5847(3) 0.3055(2) 0.0210(9) Uani 1 1 d . . . . .
H18 H 1.7286 0.5631 0.2929 0.025 Uiso 1 1 calc R U . . .
C19 C 1.4281(6) 0.6020(3) 0.2530(2) 0.0177(9) Uani 1 1 d . . . . .
H19 H 1.4396 0.592 0.2045 0.021 Uiso 1 1 calc R U . . .
Cl1 Cl 0.66928(15) 0.47823(7) -0.06048(5) 0.0187(2) Uani 1 1 d . . . . .
Cl2 Cl 0.70405(16) 0.68586(6) -0.03399(5) 0.0188(2) Uani 1 1 d . . . . .
Cu Cu 0.71648(8) 0.56905(3) 0.03405(3) 0.01476(17) Uani 1 1 d . . . . .
N1 N 0.8481(5) 0.4802(2) 0.10398(18) 0.0158(7) Uani 1 1 d . . . . .
N2 N 0.9539(5) 0.5989(2) 0.16782(17) 0.0140(7) Uani 1 1 d . . . . .
N3 N 0.7899(5) 0.6386(2) 0.12398(17) 0.0148(7) Uani 1 1 d . . . . .
S S 1.08966(18) 0.45506(7) 0.23450(6) 0.0208(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.270(5) . ?
C1 N2 1.430(5) . ?
C1 S 1.742(4) . ?
C2 N1 1.469(5) . ?
C2 C3 1.507(6) . ?
C3 C4 1.521(7) . ?
C4 S 1.814(4) . ?
C5 N3 1.327(5) . ?
C5 C6 1.419(6) . ?
C5 C8 1.471(5) . ?
C6 C7 1.366(6) . ?
C7 N2 1.371(5) . ?
C7 C14 1.480(5) . ?
C8 C9 1.389(6) . ?
C8 C13 1.399(6) . ?
C9 C10 1.389(6) . ?
C10 C11 1.381(6) . ?
C11 C12 1.394(6) . ?
C12 C13 1.379(6) . ?
C14 C19 1.390(6) . ?
C14 C15 1.393(6) . ?
C15 C16 1.380(6) . ?
C16 C17 1.387(6) . ?
C17 C18 1.389(6) . ?
C18 C19 1.388(6) . ?
Cl1 Cu 2.2816(12) . ?
Cl1 Cu 2.675(2) 3_665 ?
Cl2 Cu 2.2442(12) . ?
Cu N1 2.022(3) . ?
Cu N3 2.026(3) . ?
Cu Cl1 2.675(2) 3_665 ?
N2 N3 1.381(4) . ?

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 C1 N2 114.7(3) . . ?
N1 C1 S 130.5(3) . . ?
N2 C1 S 114.6(3) . . ?
N1 C2 C3 113.4(3) . . ?
C2 C3 C4 111.3(4) . . ?
C3 C4 S 110.9(3) . . ?
N3 C5 C6 109.6(3) . . ?
N3 C5 C8 122.2(4) . . ?
C6 C5 C8 128.0(4) . . ?
C7 C6 C5 107.0(4) . . ?
C6 C7 N2 106.4(3) . . ?
C6 C7 C14 128.6(4) . . ?
N2 C7 C14 125.1(4) . . ?
C9 C8 C13 119.2(4) . . ?
C9 C8 C5 120.1(4) . . ?
C13 C8 C5 120.7(4) . . ?
C10 C9 C8 120.6(4) . . ?
C11 C10 C9 119.9(4) . . ?
C10 C11 C12 119.9(4) . . ?
C13 C12 C11 120.3(4) . . ?
C12 C13 C8 120.1(4) . . ?
C19 C14 C15 119.7(4) . . ?
C19 C14 C7 121.6(4) . . ?
C15 C14 C7 118.7(4) . . ?
C16 C15 C14 120.4(4) . . ?
C15 C16 C17 119.8(4) . . ?
C16 C17 C18 120.1(4) . . ?
C19 C18 C17 120.1(4) . . ?
C18 C19 C14 119.9(4) . . ?
Cu Cl1 Cu 92.41(4) . 3_665 ?
N1 Cu N3 78.43(14) . . ?
N1 Cu Cl2 157.19(10) . . ?
N3 Cu Cl2 91.52(10) . . ?
N1 Cu Cl1 94.38(10) . . ?
N3 Cu Cl1 172.17(10) . . ?
Cl2 Cu Cl1 94.08(5) . . ?
N1 Cu Cl1 88.99(10) . 3_665 ?
N3 Cu Cl1 95.32(10) . 3_665 ?
Cl2 Cu Cl1 112.50(4) . 3_665 ?
Cl1 Cu Cl1 87.59(4) . 3_665 ?
C1 N1 C2 121.9(3) . . ?
C1 N1 Cu 115.6(3) . . ?
C2 N1 Cu 122.5(3) . . ?
C7 N2 N3 110.7(3) . . ?
C7 N2 C1 133.8(3) . . ?
N3 N2 C1 114.2(3) . . ?
C5 N3 N2 106.3(3) . . ?
C5 N3 Cu 140.3(3) . . ?
N2 N3 Cu 108.8(2) . . ?
C1 S C4 99.8(2) . . ?

_shelxl_version_number           2014-3

