# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_Cu169b
_database_code_depnum_ccdc_archive 'CCDC 1540061'
_audit_update_record             
;
2017-03-24 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 Cl2 Cu N3 O, C H4 O'
_chemical_formula_sum            'C20 H17 Cl2 Cu N3 O2'
_chemical_formula_weight         465.80

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9205(5)
_cell_length_b                   10.6701(6)
_cell_length_c                   12.6536(8)
_cell_angle_alpha                106.766(5)
_cell_angle_beta                 97.488(5)
_cell_angle_gamma                102.659(5)
_cell_volume                     977.37(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2464
_cell_measurement_theta_min      3.9000
_cell_measurement_theta_max      26.6160

_exptl_crystal_description       brick
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             474
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.412
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8026
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.327
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3468
_reflns_number_gt                2707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0394P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3468
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_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 0.7540(4) 0.3782(3) 0.8309(3) 0.0427(8) Uani 1 1 d . . . . .
H1 H 0.8482 0.4281 0.8911 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7617(4) 0.2565(4) 0.7617(3) 0.0513(9) Uani 1 1 d . . . . .
H2 H 0.8601 0.2247 0.7749 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6246(4) 0.1809(3) 0.6726(3) 0.0504(8) Uani 1 1 d . . . . .
H3 H 0.6282 0.0972 0.6250 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4796(4) 0.2316(3) 0.6546(3) 0.0430(7) Uani 1 1 d . . . . .
H4 H 0.3849 0.1827 0.5945 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4789(3) 0.3548(3) 0.7269(2) 0.0330(7) Uani 1 1 d . . . . .
C6 C 0.3322(3) 0.4197(3) 0.7190(2) 0.0323(6) Uani 1 1 d . . . . .
C7 C 0.1777(3) 0.3679(3) 0.6382(2) 0.0352(7) Uani 1 1 d . . . . .
H7 H 0.1595 0.2868 0.5797 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0483(3) 0.4399(3) 0.6458(2) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.0814(3) 0.5598(3) 0.7362(2) 0.0332(6) Uani 1 1 d . . . . .
H9 H -0.0032 0.6083 0.7443 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2390(3) 0.6062(3) 0.8131(2) 0.0317(6) Uani 1 1 d . . . . .
C11 C 0.2936(3) 0.7292(3) 0.9138(2) 0.0328(7) Uani 1 1 d . . . . .
C12 C 0.1880(4) 0.8151(3) 0.9459(2) 0.0404(7) Uani 1 1 d . . . . .
H12 H 0.0757 0.7982 0.9030 0.049 Uiso 1 1 calc R U . . .
C13 C 0.2521(4) 0.9256(3) 1.0418(3) 0.0469(8) Uani 1 1 d . . . . .
H13 H 0.1834 0.9848 1.0648 0.056 Uiso 1 1 calc R U . . .
C14 C 0.4167(4) 0.9486(3) 1.1035(3) 0.0480(8) Uani 1 1 d . . . . .
H14 H 0.4619 1.0239 1.1683 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5153(4) 0.8590(3) 1.0687(2) 0.0431(8) Uani 1 1 d . . . . .
H15 H 0.6269 0.8745 1.1119 0.052 Uiso 1 1 calc R U . . .
C16 C -0.1144(4) 0.3930(3) 0.5635(2) 0.0371(7) Uani 1 1 d . . . . .
C17 C -0.3062(4) 0.2525(4) 0.4154(3) 0.0651(10) Uani 1 1 d . . . . .
H17 H -0.3611 0.1770 0.3520 0.078 Uiso 1 1 calc R U . . .
C18 C -0.3725(4) 0.3545(4) 0.4529(3) 0.0531(9) Uani 1 1 d . . . . .
H18 H -0.4802 0.3639 0.4219 0.064 Uiso 1 1 calc R U . . .
C19 C -0.2509(4) 0.4469(3) 0.5486(2) 0.0415(7) Uani 1 1 d . . . . .
H19 H -0.2621 0.5295 0.5934 0.050 Uiso 1 1 calc R U . . .
N1 N 0.6153(3) 0.4288(2) 0.8154(2) 0.0372(6) Uani 1 1 d . . . . .
N2 N 0.3620(3) 0.5374(2) 0.80163(19) 0.0314(5) Uani 1 1 d . . . . .
N3 N 0.4565(3) 0.7507(2) 0.97525(19) 0.0346(6) Uani 1 1 d . . . . .
O1 O -0.1461(3) 0.2711(2) 0.48109(19) 0.0610(6) Uani 1 1 d . . . . .
Cl1 Cl 0.80877(10) 0.66656(9) 1.05370(7) 0.0556(2) Uani 1 1 d . . . . .
Cl2 Cl 0.73332(9) 0.74357(7) 0.78331(6) 0.0397(2) Uani 1 1 d . . . . .
Cu1 Cu 0.58828(4) 0.61246(4) 0.90717(3) 0.03628(14) Uani 1 1 d . . . . .
C20 C 0.9929(6) 0.9860(4) 0.6628(5) 0.1084(17) Uani 1 1 d . . . . .
H20A H 1.0365 1.0354 0.6150 0.163 Uiso 1 1 calc R U . . .
H20B H 1.0650 0.9266 0.6713 0.163 Uiso 1 1 calc R U . . .
H20C H 0.9972 1.0488 0.7354 0.163 Uiso 1 1 calc R U . . .
O2 O 0.8201(4) 0.9099(3) 0.6147(3) 0.0907(9) Uani 1 1 d . . . . .
H2A H 0.7844 0.8650 0.6540 0.136 Uiso 1 1 calc R U . . .


_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 1.343(3) . ?
C1 C2 1.360(4) . ?
C2 C3 1.369(5) . ?
C3 C4 1.393(4) . ?
C4 C5 1.370(4) . ?
C5 N1 1.358(3) . ?
C5 C6 1.484(4) . ?
C6 N2 1.332(3) . ?
C6 C7 1.378(4) . ?
C7 C8 1.407(4) . ?
C8 C9 1.395(4) . ?
C8 C16 1.436(4) . ?
C9 C10 1.373(4) . ?
C10 N2 1.341(3) . ?
C10 C11 1.475(4) . ?
C11 N3 1.352(3) . ?
C11 C12 1.384(4) . ?
C12 C13 1.369(4) . ?
C13 C14 1.361(4) . ?
C14 C15 1.375(4) . ?
C15 N3 1.336(4) . ?
C16 C19 1.349(4) . ?
C16 O1 1.359(3) . ?
C17 C18 1.305(5) . ?
C17 O1 1.364(4) . ?
C18 C19 1.399(4) . ?
N1 Cu1 2.042(2) . ?
N2 Cu1 1.941(2) . ?
N3 Cu1 2.045(2) . ?
Cl1 Cu1 2.2176(8) . ?
Cl2 Cu1 2.6007(8) . ?
C20 O2 1.383(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 C1 C2 122.4(3) . . ?
C1 C2 C3 119.9(3) . . ?
C2 C3 C4 118.7(3) . . ?
C5 C4 C3 118.9(3) . . ?
N1 C5 C4 122.0(2) . . ?
N1 C5 C6 113.4(2) . . ?
C4 C5 C6 124.6(3) . . ?
N2 C6 C7 121.2(2) . . ?
N2 C6 C5 112.7(2) . . ?
C7 C6 C5 126.0(3) . . ?
C6 C7 C8 118.8(3) . . ?
C9 C8 C7 118.2(3) . . ?
C9 C8 C16 120.0(3) . . ?
C7 C8 C16 121.8(3) . . ?
C10 C9 C8 119.8(3) . . ?
N2 C10 C9 120.5(3) . . ?
N2 C10 C11 112.8(2) . . ?
C9 C10 C11 126.7(3) . . ?
N3 C11 C12 121.8(3) . . ?
N3 C11 C10 114.3(2) . . ?
C12 C11 C10 123.9(2) . . ?
C13 C12 C11 118.7(3) . . ?
C14 C13 C12 119.7(3) . . ?
C13 C14 C15 119.2(3) . . ?
N3 C15 C14 122.3(3) . . ?
C19 C16 O1 109.4(2) . . ?
C19 C16 C8 132.7(3) . . ?
O1 C16 C8 118.0(2) . . ?
C18 C17 O1 111.3(3) . . ?
C17 C18 C19 107.0(3) . . ?
C16 C19 C18 106.7(3) . . ?
C1 N1 C5 118.1(3) . . ?
C1 N1 Cu1 127.1(2) . . ?
C5 N1 Cu1 114.71(17) . . ?
C6 N2 C10 121.3(2) . . ?
C6 N2 Cu1 119.66(18) . . ?
C10 N2 Cu1 119.03(19) . . ?
C15 N3 C11 118.2(2) . . ?
C15 N3 Cu1 127.7(2) . . ?
C11 N3 Cu1 114.10(18) . . ?
C16 O1 C17 105.6(2) . . ?
N2 Cu1 N1 79.14(9) . . ?
N2 Cu1 N3 79.52(9) . . ?
N1 Cu1 N3 156.58(9) . . ?
N2 Cu1 Cl1 164.51(7) . . ?
N1 Cu1 Cl1 99.32(7) . . ?
N3 Cu1 Cl1 98.65(7) . . ?
N2 Cu1 Cl2 93.68(7) . . ?
N1 Cu1 Cl2 94.84(7) . . ?
N3 Cu1 Cl2 96.04(6) . . ?
Cl1 Cu1 Cl2 101.82(3) . . ?

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
O2 H2A Cl2 0.82 2.38 3.195(3) 170.1 .

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.060

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_Cu171
_database_code_depnum_ccdc_archive 'CCDC 1540066'
_audit_update_record             
;
2017-03-24 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl2 Cu N4 S2'
_chemical_formula_sum            'C16 H12 Cl2 Cu N4 S2'
_chemical_formula_weight         458.86

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.3169(8)
_cell_length_b                   10.9680(5)
_cell_length_c                   7.5747(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1770.99(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3372
_cell_measurement_theta_min      3.8360
_cell_measurement_theta_max      28.8360

_exptl_crystal_description       brick
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.778
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7628
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.300
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.927
_reflns_number_total             2958
_reflns_number_gt                2650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.891
_reflns_Friedel_fraction_full    0.870

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0357P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4727(2) 0.3457(5) 0.6845(8) 0.0408(13) Uani 1 1 d . . . . .
H1 H 0.4988 0.3212 0.7760 0.049 Uiso 1 1 calc R U . . .
C2 C 0.4939(2) 0.3996(5) 0.5374(8) 0.0441(13) Uani 1 1 d . . . . .
H2 H 0.5358 0.4185 0.5167 0.053 Uiso 1 1 calc R U . . .
C3 C 0.3826(2) 0.3708(4) 0.5423(7) 0.0274(10) Uani 1 1 d . . . . .
C4 C 0.3131(2) 0.3690(4) 0.5327(6) 0.0252(10) Uani 1 1 d . . . . .
C5 C 0.27493(19) 0.4069(3) 0.3988(7) 0.0261(9) Uani 1 1 d . . . . .
H5 H 0.2921 0.4340 0.2930 0.031 Uiso 1 1 calc R U . . .
C6 C 0.20917(19) 0.4045(4) 0.4218(6) 0.0256(11) Uani 1 1 d . . . . .
C7 C 0.1871(2) 0.3601(4) 0.5847(7) 0.0311(11) Uani 1 1 d . . . . .
H7 H 0.1442 0.3587 0.6078 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2287(2) 0.3186(4) 0.7095(7) 0.0300(11) Uani 1 1 d . . . . .
C9 C 0.2155(2) 0.2609(4) 0.8788(8) 0.0306(10) Uani 1 1 d . . . . .
C10 C 0.1798(3) 0.1584(5) 1.1403(7) 0.0453(14) Uani 1 1 d . . . . .
H10 H 0.1589 0.1206 1.2331 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2421(3) 0.1739(4) 1.1317(7) 0.0398(13) Uani 1 1 d . . . . .
H11 H 0.2692 0.1478 1.2202 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1693(2) 0.4493(4) 0.2809(6) 0.0294(11) Uani 1 1 d . . . . .
C13 C 0.1869(2) 0.5186(4) 0.1381(7) 0.0333(12) Uani 1 1 d . . . . .
H13 H 0.2274 0.5451 0.1143 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1341(2) 0.5428(4) 0.0346(8) 0.0433(14) Uani 1 1 d . . . . .
H14 H 0.1327 0.5880 -0.0693 0.052 Uiso 1 1 calc R U . . .
C15 C 0.0853(2) 0.4869(5) 0.1166(8) 0.0452(15) Uani 1 1 d . . . . .
H15 H 0.0440 0.4873 0.0766 0.054 Uiso 1 1 calc R U . . .
C16 C 0.0636(2) 0.3560(5) 0.3729(10) 0.0545(15) Uani 1 1 d . . . . .
H16A H 0.0583 0.3935 0.4864 0.082 Uiso 1 1 calc R U . . .
H16B H 0.0815 0.2763 0.3875 0.082 Uiso 1 1 calc R U . . .
H16C H 0.0235 0.3491 0.3158 0.082 Uiso 1 1 calc R U . . .
N1 N 0.40902(18) 0.3299(4) 0.6880(6) 0.0332(10) Uani 1 1 d . . . . .
N2 N 0.29063(17) 0.3248(3) 0.6851(5) 0.0282(9) Uani 1 1 d . . . . .
N3 N 0.2626(2) 0.2314(3) 0.9813(6) 0.0365(10) Uani 1 1 d . . . . .
N4 N 0.10537(18) 0.4308(4) 0.2646(6) 0.0347(10) Uani 1 1 d . . . . .
S1 S 0.43460(5) 0.42908(11) 0.3934(2) 0.0383(3) Uani 1 1 d . . . . .
S2 S 0.14432(6) 0.21746(12) 0.9581(2) 0.0413(4) Uani 1 1 d . . . . .
Cl1 Cl 0.41092(7) 0.17785(12) 1.0619(2) 0.0546(4) Uani 1 1 d . . . . .
Cl2 Cl 0.35139(5) 0.49950(11) 1.00875(17) 0.0365(3) Uani 1 1 d . . . . .
Cu1 Cu 0.34795(2) 0.28163(5) 0.88085(8) 0.03406(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.340(8) . ?
C1 N1 1.368(6) . ?
C2 S1 1.701(6) . ?
C3 N1 1.318(6) . ?
C3 C4 1.483(6) . ?
C3 S1 1.705(5) . ?
C4 N2 1.342(6) . ?
C4 C5 1.365(7) . ?
C5 C6 1.413(6) . ?
C6 C7 1.408(7) . ?
C6 C12 1.450(7) . ?
C7 C8 1.375(7) . ?
C8 N2 1.334(6) . ?
C8 C9 1.458(8) . ?
C9 N3 1.309(6) . ?
C9 S2 1.700(5) . ?
C10 C11 1.340(8) . ?
C10 S2 1.702(6) . ?
C11 N3 1.373(7) . ?
C12 C13 1.373(7) . ?
C12 N4 1.384(6) . ?
C13 C14 1.396(7) . ?
C14 C15 1.359(7) . ?
C15 N4 1.349(7) . ?
C16 N4 1.463(7) . ?
N1 Cu1 2.027(4) . ?
N2 Cu1 1.979(4) . ?
N3 Cu1 2.048(4) . ?
Cl1 Cu1 2.2311(15) . ?
Cl2 Cu1 2.5796(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 114.1(5) . . ?
C1 C2 S1 111.4(4) . . ?
N1 C3 C4 117.6(4) . . ?
N1 C3 S1 113.8(3) . . ?
C4 C3 S1 128.4(4) . . ?
N2 C4 C5 122.4(4) . . ?
N2 C4 C3 108.6(4) . . ?
C5 C4 C3 128.9(4) . . ?
C4 C5 C6 119.7(4) . . ?
C7 C6 C5 116.5(4) . . ?
C7 C6 C12 124.5(4) . . ?
C5 C6 C12 118.9(4) . . ?
C8 C7 C6 120.1(4) . . ?
N2 C8 C7 121.8(4) . . ?
N2 C8 C9 109.6(4) . . ?
C7 C8 C9 128.6(4) . . ?
N3 C9 C8 118.7(4) . . ?
N3 C9 S2 113.9(4) . . ?
C8 C9 S2 127.3(4) . . ?
C11 C10 S2 110.7(4) . . ?
C10 C11 N3 114.4(5) . . ?
C13 C12 N4 106.2(4) . . ?
C13 C12 C6 127.4(4) . . ?
N4 C12 C6 126.4(4) . . ?
C12 C13 C14 109.2(4) . . ?
C15 C14 C13 105.9(5) . . ?
N4 C15 C14 110.0(4) . . ?
C3 N1 C1 111.4(4) . . ?
C3 N1 Cu1 114.7(3) . . ?
C1 N1 Cu1 133.1(4) . . ?
C8 N2 C4 119.4(4) . . ?
C8 N2 Cu1 119.7(3) . . ?
C4 N2 Cu1 120.7(3) . . ?
C9 N3 C11 111.2(5) . . ?
C9 N3 Cu1 113.2(3) . . ?
C11 N3 Cu1 135.6(4) . . ?
C15 N4 C12 108.7(4) . . ?
C15 N4 C16 121.9(4) . . ?
C12 N4 C16 129.2(4) . . ?
C2 S1 C3 89.3(3) . . ?
C9 S2 C10 89.8(3) . . ?
N2 Cu1 N1 78.12(16) . . ?
N2 Cu1 N3 78.11(17) . . ?
N1 Cu1 N3 155.32(17) . . ?
N2 Cu1 Cl1 162.57(12) . . ?
N1 Cu1 Cl1 100.94(12) . . ?
N3 Cu1 Cl1 99.73(12) . . ?
N2 Cu1 Cl2 94.44(11) . . ?
N1 Cu1 Cl2 90.61(12) . . ?
N3 Cu1 Cl2 97.75(12) . . ?
Cl1 Cu1 Cl2 102.99(5) . . ?

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
C2 H2 Cl2 0.93 2.57 3.485(5) 168.8 2_664
C5 H5 Cl2 0.93 2.60 3.524(5) 173.8 1_554
C10 H10 Cl2 0.93 2.48 3.357(6) 156.3 3_545
C13 H13 Cl2 0.93 2.81 3.647(5) 151.1 1_554

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.070

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_Cu163
_database_code_depnum_ccdc_archive 'CCDC 1540063'
_audit_update_record             
;
2017-03-24 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 Cl2 Cu N3 O S2'
_chemical_formula_sum            'C15 H9 Cl2 Cu N3 O S2'
_chemical_formula_weight         445.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8472(4)
_cell_length_b                   10.3540(6)
_cell_length_c                   11.2776(7)
_cell_angle_alpha                116.387(6)
_cell_angle_beta                 95.253(5)
_cell_angle_gamma                90.856(4)
_cell_volume                     815.80(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2777
_cell_measurement_theta_min      4.0630
_cell_measurement_theta_max      29.2140

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_F_000             446
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.929
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.13379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6826
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.367
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2888
_reflns_number_gt                2273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0346P)²+0.0408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2888
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_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 0.0949(4) 0.6088(3) 0.4573(3) 0.0352(7) Uani 1 1 d . . . . .
H1 H -0.0014 0.5607 0.3981 0.042 Uiso 1 1 calc R U . . .
C2 C 0.2437(4) 0.5456(3) 0.4571(3) 0.0400(8) Uani 1 1 d . . . . .
H2 H 0.2622 0.4504 0.3998 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2477(3) 0.7935(3) 0.6226(3) 0.0274(6) Uani 1 1 d . . . . .
C4 C 0.2691(3) 0.9424(3) 0.7279(3) 0.0264(6) Uani 1 1 d . . . . .
C5 C 0.4125(3) 1.0129(3) 0.8146(3) 0.0286(6) Uani 1 1 d . . . . .
H5 H 0.5128 0.9655 0.8121 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4041(3) 1.1581(3) 0.9070(3) 0.0280(6) Uani 1 1 d . . . . .
C7 C 0.2519(3) 1.2269(3) 0.9043(3) 0.0291(6) Uani 1 1 d . . . . .
H7 H 0.2434 1.3234 0.9635 0.035 Uiso 1 1 calc R U . . .
C8 C 0.1155(3) 1.1491(3) 0.8127(3) 0.0262(6) Uani 1 1 d . . . . .
C9 C -0.0520(3) 1.1982(3) 0.7852(3) 0.0268(6) Uani 1 1 d . . . . .
C10 C -0.3108(4) 1.3069(3) 0.7539(3) 0.0386(7) Uani 1 1 d . . . . .
H10 H -0.4013 1.3641 0.7546 0.046 Uiso 1 1 calc R U . . .
C11 C -0.3124(3) 1.1639(3) 0.6761(3) 0.0340(7) Uani 1 1 d . . . . .
H11 H -0.4056 1.1113 0.6154 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5529(3) 1.2327(3) 1.0004(3) 0.0306(7) Uani 1 1 d . . . . .
C13 C 0.7084(3) 1.1902(3) 1.0263(3) 0.0334(7) Uani 1 1 d . . . . .
H13 H 0.7469 1.0977 0.9846 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8012(4) 1.3133(3) 1.1287(3) 0.0397(8) Uani 1 1 d . . . . .
H14 H 0.9120 1.3173 1.1678 0.048 Uiso 1 1 calc R U . . .
C15 C 0.6988(4) 1.4226(3) 1.1584(3) 0.0436(8) Uani 1 1 d . . . . .
H15 H 0.7289 1.5167 1.2227 0.052 Uiso 1 1 calc R U . . .
N1 N 0.0969(3) 0.7487(2) 0.5511(2) 0.0293(5) Uani 1 1 d . . . . .
N2 N 0.1231(2) 1.0089(2) 0.7298(2) 0.0266(5) Uani 1 1 d . . . . .
N3 N -0.1647(3) 1.1021(2) 0.6938(2) 0.0300(5) Uani 1 1 d . . . . .
O1 O 0.5435(2) 1.3783(2) 1.0821(2) 0.0392(5) Uani 1 1 d . . . . .
S1 S 0.39382(9) 0.66460(7) 0.57673(9) 0.0404(2) Uani 1 1 d . . . . .
S2 S -0.11910(9) 1.36927(7) 0.85171(8) 0.0370(2) Uani 1 1 d . . . . .
Cl1 Cl -0.27369(9) 0.79603(8) 0.43262(8) 0.0414(2) Uani 1 1 d . . . . .
Cl2 Cl -0.19557(9) 0.82326(7) 0.77548(8) 0.03677(19) Uani 1 1 d . . . . .
Cu1 Cu -0.08409(4) 0.89647(3) 0.61427(3) 0.02868(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.347(4) . ?
C1 N1 1.361(3) . ?
C2 S1 1.707(3) . ?
C3 N1 1.320(3) . ?
C3 C4 1.464(4) . ?
C3 S1 1.704(3) . ?
C4 N2 1.343(3) . ?
C4 C5 1.377(4) . ?
C5 C6 1.405(4) . ?
C6 C7 1.405(4) . ?
C6 C12 1.447(4) . ?
C7 C8 1.377(4) . ?
C8 N2 1.338(3) . ?
C8 C9 1.472(3) . ?
C9 N3 1.316(3) . ?
C9 S2 1.702(3) . ?
C10 C11 1.344(4) . ?
C10 S2 1.712(3) . ?
C11 N3 1.373(3) . ?
C12 C13 1.354(4) . ?
C12 O1 1.381(3) . ?
C13 C14 1.413(4) . ?
C14 C15 1.333(4) . ?
C15 O1 1.370(3) . ?
N1 Cu1 2.036(2) . ?
N2 Cu1 1.976(2) . ?
N3 Cu1 2.046(2) . ?
Cl1 Cu1 2.2348(8) . ?
Cl2 Cu1 2.4782(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 114.5(2) . . ?
C1 C2 S1 110.5(2) . . ?
N1 C3 C4 117.9(2) . . ?
N1 C3 S1 113.4(2) . . ?
C4 C3 S1 128.68(19) . . ?
N2 C4 C5 121.6(2) . . ?
N2 C4 C3 109.8(2) . . ?
C5 C4 C3 128.6(2) . . ?
C4 C5 C6 118.6(2) . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 C12 119.2(2) . . ?
C7 C6 C12 122.1(2) . . ?
C8 C7 C6 118.9(2) . . ?
N2 C8 C7 121.5(2) . . ?
N2 C8 C9 109.4(2) . . ?
C7 C8 C9 129.1(2) . . ?
N3 C9 C8 118.0(2) . . ?
N3 C9 S2 113.7(2) . . ?
C8 C9 S2 128.20(19) . . ?
C11 C10 S2 110.6(2) . . ?
C10 C11 N3 114.3(2) . . ?
C13 C12 O1 109.7(2) . . ?
C13 C12 C6 133.3(3) . . ?
O1 C12 C6 117.1(2) . . ?
C12 C13 C14 107.0(3) . . ?
C15 C14 C13 106.6(3) . . ?
C14 C15 O1 111.3(3) . . ?
C3 N1 C1 111.7(2) . . ?
C3 N1 Cu1 113.71(18) . . ?
C1 N1 Cu1 134.34(18) . . ?
C8 N2 C4 120.5(2) . . ?
C8 N2 Cu1 119.96(16) . . ?
C4 N2 Cu1 119.49(17) . . ?
C9 N3 C11 111.6(2) . . ?
C9 N3 Cu1 113.66(17) . . ?
C11 N3 Cu1 134.74(19) . . ?
C15 O1 C12 105.5(2) . . ?
C3 S1 C2 89.83(13) . . ?
C9 S2 C10 89.81(14) . . ?
N2 Cu1 N1 78.49(9) . . ?
N2 Cu1 N3 78.25(8) . . ?
N1 Cu1 N3 153.52(8) . . ?
N2 Cu1 Cl1 158.32(7) . . ?
N1 Cu1 Cl1 97.92(7) . . ?
N3 Cu1 Cl1 99.01(7) . . ?
N2 Cu1 Cl2 96.69(7) . . ?
N1 Cu1 Cl2 97.73(7) . . ?
N3 Cu1 Cl2 97.38(7) . . ?
Cl1 Cu1 Cl2 104.98(3) . . ?

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
C5 H5 Cl2 0.93 2.70 3.629(3) 173.4 1_655
C15 H15 Cl1 0.93 2.81 3.713(3) 164.1 1_666

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.072

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_Cu190b
_database_code_depnum_ccdc_archive 'CCDC 1540064'
_audit_update_record             
;
2017-03-24 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 Cl2 Cu N3 S'
_chemical_formula_sum            'C19 H13 Cl2 Cu N3 S'
_chemical_formula_weight         449.82

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.8185(4)
_cell_length_b                   11.0960(7)
_cell_length_c                   20.4983(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.626(5)
_cell_angle_gamma                90
_cell_volume                     1769.74(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2491
_cell_measurement_theta_min      3.9860
_cell_measurement_theta_max      27.9120

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.662
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7539
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.426
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3126
_reflns_number_gt                2391
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0740P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3126
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1323
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5803(6) 0.1854(4) -0.0304(2) 0.0392(12) Uani 1 1 d . . . . .
H1 H 0.4697 0.1805 -0.0515 0.047 Uiso 1 1 calc R U . . .
C2 C 0.7080(7) 0.1162(5) -0.0530(3) 0.0450(13) Uani 1 1 d . . . . .
H2 H 0.6830 0.0632 -0.0878 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8725(7) 0.1264(4) -0.0236(2) 0.0397(12) Uani 1 1 d . . . . .
H3 H 0.9616 0.0842 -0.0401 0.048 Uiso 1 1 calc R U . . .
C4 C 0.9058(6) 0.2003(4) 0.0311(2) 0.0316(10) Uani 1 1 d . . . . .
H4 H 1.0158 0.2062 0.0527 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7706(5) 0.2643(4) 0.0524(2) 0.0254(10) Uani 1 1 d . . . . .
C6 C 0.7825(5) 0.3410(4) 0.1116(2) 0.0264(10) Uani 1 1 d . . . . .
C7 C 0.9247(5) 0.3536(4) 0.1564(2) 0.0252(10) Uani 1 1 d . . . . .
H7 H 1.0266 0.3140 0.1501 0.030 Uiso 1 1 calc R U . . .
C8 C 0.9140(5) 0.4266(4) 0.2114(2) 0.0249(9) Uani 1 1 d . . . . .
C9 C 0.7611(5) 0.4902(4) 0.2168(2) 0.0270(10) Uani 1 1 d . . . . .
H9 H 0.7513 0.5418 0.2520 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6254(5) 0.4750(4) 0.1693(2) 0.0278(10) Uani 1 1 d . . . . .
C11 C 0.4582(5) 0.5384(4) 0.1657(2) 0.0274(10) Uani 1 1 d . . . . .
C12 C 0.4143(6) 0.6248(4) 0.2085(3) 0.0354(12) Uani 1 1 d . . . . .
H12 H 0.4904 0.6461 0.2444 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2556(6) 0.6804(4) 0.1980(3) 0.0394(12) Uani 1 1 d . . . . .
H13 H 0.2241 0.7393 0.2268 0.047 Uiso 1 1 calc R U . . .
C14 C 0.1442(6) 0.6475(4) 0.1443(3) 0.0387(12) Uani 1 1 d . . . . .
H14 H 0.0376 0.6844 0.1358 0.046 Uiso 1 1 calc R U . . .
C15 C 0.1953(5) 0.5599(4) 0.1045(2) 0.0342(11) Uani 1 1 d . . . . .
H15 H 0.1200 0.5369 0.0687 0.041 Uiso 1 1 calc R U . . .
C16 C 1.0604(5) 0.4331(4) 0.2621(2) 0.0272(10) Uani 1 1 d . . . . .
C17 C 1.2119(6) 0.3690(4) 0.2639(2) 0.0375(12) Uani 1 1 d . . . . .
H17 H 1.2353 0.3114 0.2330 0.045 Uiso 1 1 calc R U . . .
C18 C 1.3268(7) 0.4019(5) 0.3183(3) 0.0511(14) Uani 1 1 d . . . . .
H18 H 1.4352 0.3678 0.3271 0.061 Uiso 1 1 calc R U . . .
C19 C 1.2656(6) 0.4867(5) 0.3561(3) 0.0466(13) Uani 1 1 d . . . . .
H19 H 1.3261 0.5178 0.3937 0.056 Uiso 1 1 calc R U . . .
N1 N 0.6094(4) 0.2593(3) 0.02086(17) 0.0305(9) Uani 1 1 d . . . . .
N2 N 0.6356(4) 0.3995(3) 0.11944(17) 0.0255(8) Uani 1 1 d . . . . .
N3 N 0.3468(4) 0.5047(3) 0.11358(18) 0.0288(8) Uani 1 1 d . . . . .
S1 S 1.06429(16) 0.53086(12) 0.32731(6) 0.0425(4) Uani 1 1 d . . . . .
Cl1 Cl 0.23859(16) 0.37431(12) -0.02694(6) 0.0457(4) Uani 1 1 d . . . . .
Cl2 Cl 0.33293(14) 0.19181(10) 0.12936(6) 0.0357(3) Uani 1 1 d . . . . .
Cu1 Cu 0.43310(6) 0.36544(5) 0.05992(3) 0.0292(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.334(6) . ?
C1 C2 1.376(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.360(5) . ?
C5 C6 1.479(6) . ?
C6 N2 1.343(5) . ?
C6 C7 1.377(6) . ?
C7 C8 1.398(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.402(6) . ?
C8 C16 1.471(6) . ?
C9 C10 1.379(6) . ?
C9 H9 0.9300 . ?
C10 N2 1.330(5) . ?
C10 C11 1.480(6) . ?
C11 N3 1.363(6) . ?
C11 C12 1.366(6) . ?
C12 C13 1.383(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(7) . ?
C14 H14 0.9300 . ?
C15 N3 1.329(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(6) . ?
C16 S1 1.718(4) . ?
C17 C18 1.410(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.337(7) . ?
C18 H18 0.9300 . ?
C19 S1 1.698(5) . ?
C19 H19 0.9300 . ?
N1 Cu1 2.036(4) . ?
N2 Cu1 1.939(3) . ?
N3 Cu1 2.050(4) . ?
Cl1 Cu1 2.2274(13) . ?
Cl2 Cu1 2.5631(13) . ?

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 C2 122.4(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.0(4) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 122.1(4) . . ?
N1 C5 C6 113.2(4) . . ?
C4 C5 C6 124.6(4) . . ?
N2 C6 C7 121.1(4) . . ?
N2 C6 C5 113.0(4) . . ?
C7 C6 C5 126.0(4) . . ?
C6 C7 C8 119.2(4) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C9 118.4(4) . . ?
C7 C8 C16 119.7(4) . . ?
C9 C8 C16 122.0(4) . . ?
C10 C9 C8 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N2 C10 C9 121.3(4) . . ?
N2 C10 C11 112.4(4) . . ?
C9 C10 C11 126.3(4) . . ?
N3 C11 C12 120.9(4) . . ?
N3 C11 C10 113.7(4) . . ?
C12 C11 C10 125.4(4) . . ?
C11 C12 C13 119.4(5) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 119.4(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 117.9(4) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
N3 C15 C14 123.9(5) . . ?
N3 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
C17 C16 C8 126.8(4) . . ?
C17 C16 S1 110.8(3) . . ?
C8 C16 S1 122.3(3) . . ?
C16 C17 C18 111.4(4) . . ?
C16 C17 H17 124.3 . . ?
C18 C17 H17 124.3 . . ?
C19 C18 C17 113.9(5) . . ?
C19 C18 H18 123.1 . . ?
C17 C18 H18 123.1 . . ?
C18 C19 S1 111.9(4) . . ?
C18 C19 H19 124.0 . . ?
S1 C19 H19 124.0 . . ?
C1 N1 C5 118.5(4) . . ?
C1 N1 Cu1 126.5(3) . . ?
C5 N1 Cu1 114.9(3) . . ?
C10 N2 C6 120.8(4) . . ?
C10 N2 Cu1 120.0(3) . . ?
C6 N2 Cu1 119.1(3) . . ?
C15 N3 C11 118.4(4) . . ?
C15 N3 Cu1 127.4(3) . . ?
C11 N3 Cu1 114.1(3) . . ?
C19 S1 C16 91.9(2) . . ?
N2 Cu1 N1 79.48(14) . . ?
N2 Cu1 N3 78.87(14) . . ?
N1 Cu1 N3 156.74(14) . . ?
N2 Cu1 Cl1 161.05(11) . . ?
N1 Cu1 Cl1 98.44(11) . . ?
N3 Cu1 Cl1 99.25(11) . . ?
N2 Cu1 Cl2 94.13(11) . . ?
N1 Cu1 Cl2 92.23(11) . . ?
N3 Cu1 Cl2 97.71(10) . . ?
Cl1 Cu1 Cl2 104.79(5) . . ?

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
C4 H4 Cl2 0.93 2.81 3.728(5) 170.8 1_655
C7 H7 Cl2 0.93 2.82 3.750(4) 179.1 1_655
C9 H9 S1 0.93 2.76 3.146(4) 105.7 .
C17 H17 Cl2 0.93 2.68 3.588(5) 165.9 1_655

_refine_diff_density_max         1.038
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.136

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_Cu178
_database_code_depnum_ccdc_archive 'CCDC 1540062'
_audit_update_record             
;
2017-03-24 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl2 Cu N4'
_chemical_formula_sum            'C20 H16 Cl2 Cu N4'
_chemical_formula_weight         446.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3952(3)
_cell_length_b                   12.8556(4)
_cell_length_c                   16.9843(6)
_cell_angle_alpha                72.580(3)
_cell_angle_beta                 81.358(3)
_cell_angle_gamma                73.642(3)
_cell_volume                     1873.19(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    6526
_cell_measurement_theta_min      3.7670
_cell_measurement_theta_max      28.1320

_exptl_crystal_description       brick
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.464
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15611
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.295
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             6636
_reflns_number_gt                5266
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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+0.2943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6636
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_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 0.6267(3) 0.6819(2) 0.5322(2) 0.0454(8) Uani 1 1 d . . . . .
H1 H 0.5529 0.7408 0.5043 0.055 Uiso 1 1 calc R U . . .
C2 C 0.6757(4) 0.6905(3) 0.6019(2) 0.0488(8) Uani 1 1 d . . . . .
H2 H 0.6342 0.7536 0.6215 0.059 Uiso 1 1 calc R U . . .
C3 C 0.7861(4) 0.6053(3) 0.6419(2) 0.0473(8) Uani 1 1 d . . . . .
H3 H 0.8210 0.6100 0.6888 0.057 Uiso 1 1 calc R U . . .
C4 C 0.8458(3) 0.5116(2) 0.61207(18) 0.0393(7) Uani 1 1 d . . . . .
H4 H 0.9213 0.4528 0.6384 0.047 Uiso 1 1 calc R U . . .
C5 C 0.7909(3) 0.5075(2) 0.54284(17) 0.0320(6) Uani 1 1 d . . . . .
C6 C 0.8428(3) 0.4104(2) 0.50596(17) 0.0315(6) Uani 1 1 d . . . . .
C7 C 0.9549(3) 0.3154(2) 0.53209(18) 0.0356(7) Uani 1 1 d . . . . .
H7 H 1.0087 0.3082 0.5759 0.043 Uiso 1 1 calc R U . . .
C8 C 0.9880(3) 0.2290(2) 0.49230(18) 0.0364(7) Uani 1 1 d . . . . .
C9 C 0.9001(3) 0.2456(2) 0.42733(19) 0.0404(7) Uani 1 1 d . . . . .
H9 H 0.9146 0.1891 0.4011 0.048 Uiso 1 1 calc R U . . .
C10 C 0.7932(3) 0.3443(2) 0.40217(17) 0.0358(7) Uani 1 1 d . . . . .
C11 C 0.6963(3) 0.3766(3) 0.33309(18) 0.0407(7) Uani 1 1 d . . . . .
C12 C 0.6969(4) 0.3071(3) 0.2842(2) 0.0509(8) Uani 1 1 d . . . . .
H12 H 0.7587 0.2346 0.2945 0.061 Uiso 1 1 calc R U . . .
C13 C 0.6043(4) 0.3473(4) 0.2201(2) 0.0612(10) Uani 1 1 d . . . . .
H13 H 0.6027 0.3021 0.1867 0.073 Uiso 1 1 calc R U . . .
C14 C 0.5147(4) 0.4548(4) 0.2062(2) 0.0654(11) Uani 1 1 d . . . . .
H14 H 0.4534 0.4839 0.1624 0.078 Uiso 1 1 calc R U . . .
C15 C 0.5164(4) 0.5192(3) 0.2579(2) 0.0539(9) Uani 1 1 d . . . . .
H15 H 0.4536 0.5912 0.2490 0.065 Uiso 1 1 calc R U . . .
C16 C 1.1088(3) 0.1302(2) 0.5213(2) 0.0419(7) Uani 1 1 d . . . . .
C17 C 1.1709(4) 0.0957(3) 0.5967(2) 0.0570(9) Uani 1 1 d . . . . .
H17 H 1.1409 0.1304 0.6393 0.068 Uiso 1 1 calc R U . . .
C18 C 1.2866(5) -0.0004(3) 0.5973(3) 0.0761(12) Uani 1 1 d . . . . .
H18 H 1.3482 -0.0408 0.6401 0.091 Uiso 1 1 calc R U . . .
C19 C 1.2926(4) -0.0240(3) 0.5246(3) 0.0702(11) Uani 1 1 d . . . . .
H19 H 1.3599 -0.0843 0.5092 0.084 Uiso 1 1 calc R U . . .
C20 C 1.1706(5) 0.0538(3) 0.3939(3) 0.0746(12) Uani 1 1 d . . . . .
H20A H 1.0783 0.0368 0.3917 0.112 Uiso 1 1 calc R U . . .
H20B H 1.2518 -0.0021 0.3776 0.112 Uiso 1 1 calc R U . . .
H20C H 1.1717 0.1266 0.3570 0.112 Uiso 1 1 calc R U . . .
N1 N 0.6823(3) 0.59102(18) 0.50338(15) 0.0357(5) Uani 1 1 d . . . . .
N2 N 0.7669(3) 0.42529(18) 0.44112(14) 0.0328(5) Uani 1 1 d . . . . .
N3 N 0.6056(3) 0.4812(2) 0.32059(15) 0.0421(6) Uani 1 1 d . . . . .
N4 N 1.1854(3) 0.0538(2) 0.47674(19) 0.0539(7) Uani 1 1 d . . . . .
Cl1 Cl 0.41755(8) 0.70697(7) 0.37822(5) 0.0531(2) Uani 1 1 d . . . . .
Cl2 Cl 0.81953(8) 0.65985(6) 0.30588(5) 0.04301(19) Uani 1 1 d . . . . .
Cu1 Cu 0.62919(4) 0.57041(3) 0.39766(2) 0.03680(11) Uani 1 1 d . . . . .
C21 C 0.5159(3) 0.0273(2) 1.18228(19) 0.0419(7) Uani 1 1 d . . . . .
H21 H 0.5448 0.0742 1.2058 0.050 Uiso 1 1 calc R U . . .
C22 C 0.5662(3) -0.0866(2) 1.21301(19) 0.0440(7) Uani 1 1 d . . . . .
H22 H 0.6256 -0.1167 1.2576 0.053 Uiso 1 1 calc R U . . .
C23 C 0.5270(3) -0.1558(2) 1.17653(18) 0.0396(7) Uani 1 1 d . . . . .
H23 H 0.5628 -0.2336 1.1951 0.048 Uiso 1 1 calc R U . . .
C24 C 0.4351(3) -0.1099(2) 1.11259(17) 0.0335(6) Uani 1 1 d . . . . .
H24 H 0.4076 -0.1560 1.0876 0.040 Uiso 1 1 calc R U . . .
C25 C 0.3840(3) 0.0058(2) 1.08598(16) 0.0292(6) Uani 1 1 d . . . . .
C26 C 0.2817(3) 0.0674(2) 1.01931(16) 0.0277(6) Uani 1 1 d . . . . .
C27 C 0.2133(3) 0.0225(2) 0.97562(17) 0.0319(6) Uani 1 1 d . . . . .
H27 H 0.2291 -0.0552 0.9874 0.038 Uiso 1 1 calc R U . . .
C28 C 0.1201(3) 0.0936(2) 0.91364(17) 0.0309(6) Uani 1 1 d . . . . .
C29 C 0.1001(3) 0.2107(2) 0.89824(17) 0.0325(6) Uani 1 1 d . . . . .
H29 H 0.0403 0.2610 0.8571 0.039 Uiso 1 1 calc R U . . .
C30 C 0.1706(3) 0.2498(2) 0.94516(17) 0.0298(6) Uani 1 1 d . . . . .
C31 C 0.1624(3) 0.3703(2) 0.93593(17) 0.0317(6) Uani 1 1 d . . . . .
C32 C 0.0828(3) 0.4598(2) 0.87947(19) 0.0418(7) Uani 1 1 d . . . . .
H32 H 0.0320 0.4482 0.8412 0.050 Uiso 1 1 calc R U . . .
C33 C 0.0792(3) 0.5676(2) 0.8803(2) 0.0463(8) Uani 1 1 d . . . . .
H33 H 0.0236 0.6297 0.8435 0.056 Uiso 1 1 calc R U . . .
C34 C 0.1586(3) 0.5821(2) 0.9361(2) 0.0455(8) Uani 1 1 d . . . . .
H34 H 0.1575 0.6540 0.9376 0.055 Uiso 1 1 calc R U . . .
C35 C 0.2391(3) 0.4897(2) 0.9893(2) 0.0437(8) Uani 1 1 d . . . . .
H35 H 0.2949 0.5000 1.0258 0.052 Uiso 1 1 calc R U . . .
C36 C 0.0522(3) 0.0435(2) 0.86683(17) 0.0339(6) Uani 1 1 d . . . . .
C37 C 0.0867(3) -0.0689(3) 0.8677(2) 0.0458(8) Uani 1 1 d . . . . .
H37 H 0.1587 -0.1263 0.8980 0.055 Uiso 1 1 calc R U . . .
C38 C -0.0047(4) -0.0814(3) 0.8155(2) 0.0528(9) Uani 1 1 d . . . . .
H38 H -0.0045 -0.1480 0.8043 0.063 Uiso 1 1 calc R U . . .
C39 C -0.0940(4) 0.0223(3) 0.7842(2) 0.0501(9) Uani 1 1 d . . . . .
H39 H -0.1672 0.0383 0.7479 0.060 Uiso 1 1 calc R U . . .
C40 C -0.1398(4) 0.2175(3) 0.7912(2) 0.0531(9) Uani 1 1 d . . . . .
H40A H -0.1805 0.2404 0.8405 0.080 Uiso 1 1 calc R U . . .
H40B H -0.2189 0.2282 0.7575 0.080 Uiso 1 1 calc R U . . .
H40C H -0.0724 0.2619 0.7609 0.080 Uiso 1 1 calc R U . . .
N5 N 0.4267(2) 0.07419(18) 1.11960(14) 0.0343(5) Uani 1 1 d . . . . .
N6 N 0.2576(2) 0.17974(17) 1.00349(14) 0.0288(5) Uani 1 1 d . . . . .
N7 N 0.2408(2) 0.38437(18) 0.99090(14) 0.0339(5) Uani 1 1 d . . . . .
N8 N -0.0603(3) 0.0990(2) 0.81364(15) 0.0382(6) Uani 1 1 d . . . . .
Cl3 Cl 0.27720(9) 0.28445(7) 1.19206(5) 0.0546(2) Uani 1 1 d . . . . .
Cl4 Cl 0.59087(8) 0.28028(6) 1.01907(5) 0.0479(2) Uani 1 1 d . . . . .
Cu2 Cu 0.35301(4) 0.24098(3) 1.06777(2) 0.03438(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.342(3) . ?
C1 C2 1.378(4) . ?
C2 C3 1.365(5) . ?
C3 C4 1.386(4) . ?
C4 C5 1.373(4) . ?
C5 N1 1.342(3) . ?
C5 C6 1.491(3) . ?
C6 N2 1.338(3) . ?
C6 C7 1.374(4) . ?
C7 C8 1.407(4) . ?
C8 C9 1.406(4) . ?
C8 C16 1.458(4) . ?
C9 C10 1.374(4) . ?
C10 N2 1.343(3) . ?
C10 C11 1.481(4) . ?
C11 N3 1.348(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.379(5) . ?
C13 C14 1.373(5) . ?
C14 C15 1.380(5) . ?
C15 N3 1.342(4) . ?
C16 C17 1.384(5) . ?
C16 N4 1.393(4) . ?
C17 C18 1.395(5) . ?
C18 C19 1.346(5) . ?
C19 N4 1.366(5) . ?
C20 N4 1.434(5) . ?
N1 Cu1 2.043(2) . ?
N2 Cu1 1.950(2) . ?
N3 Cu1 2.051(2) . ?
Cl1 Cu1 2.2424(8) . ?
Cl2 Cu1 2.4894(8) . ?
C21 N5 1.341(4) . ?
C21 C22 1.366(4) . ?
C22 C23 1.376(4) . ?
C23 C24 1.373(4) . ?
C24 C25 1.382(4) . ?
C25 N5 1.352(3) . ?
C25 C26 1.482(4) . ?
C26 N6 1.346(3) . ?
C26 C27 1.380(3) . ?
C27 C28 1.400(4) . ?
C28 C29 1.411(4) . ?
C28 C36 1.464(3) . ?
C29 C30 1.382(4) . ?
C30 N6 1.325(3) . ?
C30 C31 1.491(3) . ?
C31 N7 1.353(3) . ?
C31 C32 1.369(4) . ?
C32 C33 1.380(4) . ?
C33 C34 1.374(4) . ?
C34 C35 1.361(4) . ?
C35 N7 1.341(3) . ?
C36 C37 1.385(4) . ?
C36 N8 1.385(4) . ?
C37 C38 1.393(4) . ?
C38 C39 1.358(5) . ?
C39 N8 1.357(4) . ?
C40 N8 1.456(4) . ?
N5 Cu2 2.017(2) . ?
N6 Cu2 1.955(2) . ?
N7 Cu2 2.023(2) . ?
Cl3 Cu2 2.3034(8) . ?
Cl4 Cu2 2.4008(8) . ?

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 C2 121.8(3) . . ?
C3 C2 C1 119.2(3) . . ?
C2 C3 C4 119.5(3) . . ?
C5 C4 C3 118.5(3) . . ?
N1 C5 C4 122.2(2) . . ?
N1 C5 C6 114.1(2) . . ?
C4 C5 C6 123.7(3) . . ?
N2 C6 C7 121.7(2) . . ?
N2 C6 C5 111.8(2) . . ?
C7 C6 C5 126.5(2) . . ?
C6 C7 C8 119.8(3) . . ?
C9 C8 C7 116.6(3) . . ?
C9 C8 C16 125.3(2) . . ?
C7 C8 C16 118.1(3) . . ?
C10 C9 C8 120.8(2) . . ?
N2 C10 C9 120.6(3) . . ?
N2 C10 C11 112.0(3) . . ?
C9 C10 C11 127.5(2) . . ?
N3 C11 C12 121.7(3) . . ?
N3 C11 C10 114.3(2) . . ?
C12 C11 C10 124.0(3) . . ?
C13 C12 C11 119.0(3) . . ?
C14 C13 C12 119.2(3) . . ?
C13 C14 C15 119.3(3) . . ?
N3 C15 C14 122.2(3) . . ?
C17 C16 N4 107.1(3) . . ?
C17 C16 C8 127.0(3) . . ?
N4 C16 C8 125.8(3) . . ?
C16 C17 C18 107.9(3) . . ?
C19 C18 C17 107.5(4) . . ?
C18 C19 N4 110.1(3) . . ?
C5 N1 C1 118.8(2) . . ?
C5 N1 Cu1 114.92(16) . . ?
C1 N1 Cu1 126.1(2) . . ?
C6 N2 C10 120.4(2) . . ?
C6 N2 Cu1 119.49(17) . . ?
C10 N2 Cu1 119.87(19) . . ?
C15 N3 C11 118.6(3) . . ?
C15 N3 Cu1 126.4(2) . . ?
C11 N3 Cu1 114.88(19) . . ?
C19 N4 C16 107.5(3) . . ?
C19 N4 C20 122.5(3) . . ?
C16 N4 C20 129.8(3) . . ?
N2 Cu1 N1 78.83(9) . . ?
N2 Cu1 N3 78.70(9) . . ?
N1 Cu1 N3 155.78(10) . . ?
N2 Cu1 Cl1 160.41(7) . . ?
N1 Cu1 Cl1 98.36(7) . . ?
N3 Cu1 Cl1 99.78(8) . . ?
N2 Cu1 Cl2 95.70(7) . . ?
N1 Cu1 Cl2 95.03(7) . . ?
N3 Cu1 Cl2 96.05(7) . . ?
Cl1 Cu1 Cl2 103.87(3) . . ?
N5 C21 C22 122.7(3) . . ?
C21 C22 C23 118.6(3) . . ?
C24 C23 C22 119.9(3) . . ?
C23 C24 C25 118.8(2) . . ?
N5 C25 C24 121.4(2) . . ?
N5 C25 C26 113.5(2) . . ?
C24 C25 C26 125.1(2) . . ?
N6 C26 C27 120.3(2) . . ?
N6 C26 C25 112.0(2) . . ?
C27 C26 C25 127.7(2) . . ?
C26 C27 C28 120.2(2) . . ?
C27 C28 C29 117.5(2) . . ?
C27 C28 C36 119.0(2) . . ?
C29 C28 C36 123.4(3) . . ?
C30 C29 C28 119.1(3) . . ?
N6 C30 C29 121.5(2) . . ?
N6 C30 C31 112.8(2) . . ?
C29 C30 C31 125.7(2) . . ?
N7 C31 C32 121.9(2) . . ?
N7 C31 C30 113.1(2) . . ?
C32 C31 C30 125.0(2) . . ?
C31 C32 C33 119.0(3) . . ?
C34 C33 C32 119.2(3) . . ?
C35 C34 C33 119.1(3) . . ?
N7 C35 C34 122.5(3) . . ?
C37 C36 N8 106.5(2) . . ?
C37 C36 C28 126.7(3) . . ?
N8 C36 C28 126.8(2) . . ?
C36 C37 C38 108.5(3) . . ?
C39 C38 C37 106.8(3) . . ?
N8 C39 C38 109.7(3) . . ?
C21 N5 C25 118.5(2) . . ?
C21 N5 Cu2 125.39(18) . . ?
C25 N5 Cu2 116.04(18) . . ?
C30 N6 C26 121.3(2) . . ?
C30 N6 Cu2 119.28(16) . . ?
C26 N6 Cu2 119.40(18) . . ?
C35 N7 C31 118.2(2) . . ?
C35 N7 Cu2 126.19(19) . . ?
C31 N7 Cu2 115.56(17) . . ?
C39 N8 C36 108.5(2) . . ?
C39 N8 C40 121.9(3) . . ?
C36 N8 C40 129.6(2) . . ?
N6 Cu2 N5 78.96(9) . . ?
N6 Cu2 N7 79.20(9) . . ?
N5 Cu2 N7 158.16(8) . . ?
N6 Cu2 Cl3 130.72(7) . . ?
N5 Cu2 Cl3 94.65(7) . . ?
N7 Cu2 Cl3 99.37(6) . . ?
N6 Cu2 Cl4 119.99(7) . . ?
N5 Cu2 Cl4 97.61(7) . . ?
N7 Cu2 Cl4 93.49(7) . . ?
Cl3 Cu2 Cl4 109.29(3) . . ?

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
C4 H4 Cl2 0.93 2.61 3.501(3) 160.9 2_766

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_Cu165
_database_code_depnum_ccdc_archive 'CCDC 1540065'
_audit_update_record             
;
2017-03-24 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 Cl2 Cu N3 S3'
_chemical_formula_sum            'C15 H9 Cl2 Cu N3 S3'
_chemical_formula_weight         461.87

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8330(4)
_cell_length_b                   10.9863(8)
_cell_length_c                   11.2152(8)
_cell_angle_alpha                118.351(7)
_cell_angle_beta                 92.578(5)
_cell_angle_gamma                91.767(6)
_cell_volume                     847.01(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2214
_cell_measurement_theta_min      3.6920
_cell_measurement_theta_max      28.5260

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_F_000             462
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.976
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6680
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.361
_diffrn_reflns_theta_max         25.044
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2993
_reflns_number_gt                2409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2993
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1013(4) -0.4023(4) -0.0514(3) 0.0335(8) Uani 1 1 d . . . . .
H1 H 0.0066 -0.4526 -0.1089 0.040 Uiso 1 1 calc R U . . .
C2 C 0.2528(5) -0.4589(4) -0.0526(4) 0.0401(9) Uani 1 1 d . . . . .
H2 H 0.2747 -0.5508 -0.1097 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2478(4) -0.2177(3) 0.1119(3) 0.0263(7) Uani 1 1 d . . . . .
C4 C 0.2649(4) -0.0711(3) 0.2162(3) 0.0266(7) Uani 1 1 d . . . . .
C5 C 0.4043(4) 0.0003(4) 0.3056(3) 0.0294(8) Uani 1 1 d . . . . .
H5 H 0.5041 -0.0442 0.3037 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3929(4) 0.1403(4) 0.3988(3) 0.0269(7) Uani 1 1 d . . . . .
C7 C 0.2404(4) 0.2028(4) 0.3937(3) 0.0315(8) Uani 1 1 d . . . . .
H7 H 0.2286 0.2959 0.4534 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1088(4) 0.1252(4) 0.2996(3) 0.0282(8) Uani 1 1 d . . . . .
C9 C -0.0561(4) 0.1707(4) 0.2717(3) 0.0287(8) Uani 1 1 d . . . . .
C10 C -0.3096(4) 0.2715(4) 0.2371(3) 0.0387(9) Uani 1 1 d . . . . .
H10 H -0.3983 0.3254 0.2360 0.046 Uiso 1 1 calc R U . . .
C11 C -0.3097(4) 0.1336(4) 0.1604(3) 0.0355(9) Uani 1 1 d . . . . .
H11 H -0.4010 0.0816 0.0993 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5361(4) 0.2192(3) 0.4953(3) 0.0298(8) Uani 1 1 d . . . . .
C13 C 0.6903(4) 0.1729(4) 0.5165(3) 0.0316(8) Uani 1 1 d . . . . .
H13 H 0.7184 0.0809 0.4704 0.038 Uiso 1 1 calc R U . . .
C14 C 0.8007(5) 0.2809(4) 0.6161(3) 0.0432(10) Uani 1 1 d . . . . .
H14 H 0.9094 0.2674 0.6429 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7323(5) 0.4050(4) 0.6679(4) 0.0457(10) Uani 1 1 d . . . . .
H15 H 0.7889 0.4869 0.7335 0.055 Uiso 1 1 calc R U . . .
N1 N 0.0990(3) -0.2654(3) 0.0412(3) 0.0289(7) Uani 1 1 d . . . . .
N2 N 0.1201(3) -0.0096(3) 0.2159(3) 0.0274(6) Uani 1 1 d . . . . .
N3 N -0.1653(3) 0.0743(3) 0.1784(3) 0.0304(7) Uani 1 1 d . . . . .
S1 S 0.39768(11) -0.33768(10) 0.06531(9) 0.0384(3) Uani 1 1 d . . . . .
S2 S -0.12320(11) 0.33417(10) 0.33735(9) 0.0376(2) Uani 1 1 d . . . . .
S3 S 0.53067(12) 0.39535(10) 0.59993(9) 0.0452(3) Uani 1 1 d . . . . .
Cl1 Cl -0.26689(11) -0.22410(10) -0.08234(8) 0.0411(3) Uani 1 1 d . . . . .
Cl2 Cl -0.20300(11) -0.17960(9) 0.26993(8) 0.0353(2) Uani 1 1 d . . . . .
Cu1 Cu -0.08366(5) -0.12246(4) 0.10174(4) 0.02909(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.354(5) . ?
C1 N1 1.364(4) . ?
C2 S1 1.706(4) . ?
C3 N1 1.321(4) . ?
C3 C4 1.471(5) . ?
C3 S1 1.699(3) . ?
C4 N2 1.339(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.399(5) . ?
C6 C7 1.408(4) . ?
C6 C12 1.456(4) . ?
C7 C8 1.377(4) . ?
C8 N2 1.333(4) . ?
C8 C9 1.473(4) . ?
C9 N3 1.327(4) . ?
C9 S2 1.697(3) . ?
C10 C11 1.341(5) . ?
C10 S2 1.710(4) . ?
C11 N3 1.377(4) . ?
C12 C13 1.379(4) . ?
C12 S3 1.725(3) . ?
C13 C14 1.412(5) . ?
C14 C15 1.343(6) . ?
C15 S3 1.701(4) . ?
N1 Cu1 2.046(3) . ?
N2 Cu1 1.977(2) . ?
N3 Cu1 2.047(3) . ?
Cl1 Cu1 2.2392(9) . ?
Cl2 Cu1 2.4643(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 114.5(3) . . ?
C1 C2 S1 110.3(3) . . ?
N1 C3 C4 117.7(3) . . ?
N1 C3 S1 113.7(2) . . ?
C4 C3 S1 128.5(2) . . ?
N2 C4 C5 121.8(3) . . ?
N2 C4 C3 110.0(3) . . ?
C5 C4 C3 128.2(3) . . ?
C4 C5 C6 119.0(3) . . ?
C5 C6 C7 117.8(3) . . ?
C5 C6 C12 120.8(3) . . ?
C7 C6 C12 121.3(3) . . ?
C8 C7 C6 119.6(3) . . ?
N2 C8 C7 121.4(3) . . ?
N2 C8 C9 110.0(3) . . ?
C7 C8 C9 128.6(3) . . ?
N3 C9 C8 117.1(3) . . ?
N3 C9 S2 114.3(2) . . ?
C8 C9 S2 128.4(3) . . ?
C11 C10 S2 110.3(3) . . ?
C10 C11 N3 115.3(3) . . ?
C13 C12 C6 128.5(3) . . ?
C13 C12 S3 110.4(2) . . ?
C6 C12 S3 121.1(2) . . ?
C12 C13 C14 112.4(3) . . ?
C15 C14 C13 113.0(3) . . ?
C14 C15 S3 112.4(3) . . ?
C3 N1 C1 111.4(3) . . ?
C3 N1 Cu1 113.7(2) . . ?
C1 N1 Cu1 134.8(2) . . ?
C8 N2 C4 120.3(3) . . ?
C8 N2 Cu1 119.9(2) . . ?
C4 N2 Cu1 119.7(2) . . ?
C9 N3 C11 110.2(3) . . ?
C9 N3 Cu1 113.9(2) . . ?
C11 N3 Cu1 136.0(2) . . ?
C3 S1 C2 90.01(16) . . ?
C9 S2 C10 89.88(17) . . ?
C15 S3 C12 91.88(18) . . ?
N2 Cu1 N1 78.43(10) . . ?
N2 Cu1 N3 78.13(10) . . ?
N1 Cu1 N3 153.72(11) . . ?
N2 Cu1 Cl1 157.24(9) . . ?
N1 Cu1 Cl1 99.16(7) . . ?
N3 Cu1 Cl1 97.85(7) . . ?
N2 Cu1 Cl2 97.06(8) . . ?
N1 Cu1 Cl2 96.79(8) . . ?
N3 Cu1 Cl2 97.72(8) . . ?
Cl1 Cu1 Cl2 105.68(4) . . ?

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
C2 H2 Cl2 0.93 2.66 3.534(4) 157.1 2_545
C5 H5 Cl2 0.93 2.72 3.641(3) 173.8 1_655
C7 H7 S3 0.93 2.70 3.095(3) 106.7 .
C13 H13 Cl2 0.93 2.78 3.685(4) 163.6 1_655
C14 H14 Cl2 0.93 2.83 3.743(4) 167.5 2_656

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.082

_shelxl_version_number           2014/6

