# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1850384'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 Cl N6'
_chemical_formula_sum            'C8 H7 Cl N6'
_chemical_formula_weight         222.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   4.1825(5)
_cell_length_b                   23.824(2)
_cell_length_c                   9.9296(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.827(10)
_cell_angle_gamma                90
_cell_volume                     980.22(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    152(2)
_cell_measurement_reflns_used    1679
_cell_measurement_theta_min      3.6780
_cell_measurement_theta_max      72.0680

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.265
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.20518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      152(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova(Cu) micro-focus sealed X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_reflns_number            3064
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.711
_diffrn_reflns_theta_max         72.252
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             1783
_reflns_number_gt                1433
_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1792P)²+0.1316P] 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         1783
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2537
_refine_ls_wR_factor_gt          0.2149
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 -0.3411(9) 0.47357(15) -0.3095(3) 0.0547(9) Uani 1 1 d . . . . .
H1 H -0.294414 0.509814 -0.335636 0.066 Uiso 1 1 calc R U . . .
C2 C -0.2640(10) 0.42951(18) -0.3882(3) 0.0607(9) Uani 1 1 d . . . . .
H2A H -0.168708 0.435712 -0.466261 0.073 Uiso 1 1 calc R U . . .
C3 C -0.3317(10) 0.37586(16) -0.3486(4) 0.0608(9) Uani 1 1 d . . . . .
H3 H -0.283099 0.345048 -0.399617 0.073 Uiso 1 1 calc R U . . .
C4 C -0.4719(9) 0.36859(13) -0.2326(3) 0.0517(8) Uani 1 1 d . . . . .
H4 H -0.515423 0.332708 -0.203001 0.062 Uiso 1 1 calc R U . . .
C5 C -0.5473(7) 0.41507(12) -0.1605(3) 0.0418(7) Uani 1 1 d . . . . .
C6 C -0.7070(8) 0.41005(14) -0.0334(3) 0.0490(8) Uani 1 1 d . . . . .
H6A H -0.883217 0.436762 -0.038079 0.059 Uiso 1 1 calc R U . . .
H6B H -0.797164 0.372687 -0.029158 0.059 Uiso 1 1 calc R U . . .
C7 C -0.3207(7) 0.37988(12) 0.1641(3) 0.0394(7) Uani 1 1 d . . . . .
C8 C -0.0342(8) 0.30560(13) 0.3187(3) 0.0477(8) Uani 1 1 d . . . . .
N1 N -0.4798(7) 0.46688(11) -0.1973(2) 0.0470(7) Uani 1 1 d . . . . .
N2 N -0.4818(7) 0.42040(11) 0.0901(2) 0.0466(7) Uani 1 1 d . . . . .
H2 H -0.451013 0.454552 0.116750 0.056 Uiso 1 1 calc R U . . .
N3 N -0.3772(8) 0.32595(11) 0.1300(3) 0.0557(8) Uani 1 1 d . . . . .
N4 N -0.2305(9) 0.28758(11) 0.2137(3) 0.0585(8) Uani 1 1 d . . . . .
N5 N 0.0378(8) 0.35873(12) 0.3508(3) 0.0547(8) Uani 1 1 d . . . . .
N6 N -0.1069(8) 0.39745(11) 0.2712(3) 0.0526(7) Uani 1 1 d . . . . .
CL1 Cl 0.1558(3) 0.25664(4) 0.42951(10) 0.0741(5) 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(4) . ?
C1 C2 1.373(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.328(4) . ?
C5 C6 1.511(5) . ?
C6 N2 1.462(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.338(4) . ?
C7 N3 1.341(4) . ?
C7 N6 1.359(4) . ?
C8 N4 1.309(5) . ?
C8 N5 1.330(5) . ?
C8 CL1 1.722(3) . ?
N2 H2 0.8600 . ?
N3 N4 1.328(4) . ?
N5 N6 1.308(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 C2 123.2(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 C6 116.0(3) . . ?
C4 C5 C6 121.9(3) . . ?
N2 C6 C5 112.3(3) . . ?
N2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 N3 119.6(3) . . ?
N2 C7 N6 115.9(3) . . ?
N3 C7 N6 124.5(3) . . ?
N4 C8 N5 126.9(3) . . ?
N4 C8 CL1 118.2(3) . . ?
N5 C8 CL1 114.9(2) . . ?
C5 N1 C1 118.3(3) . . ?
C7 N2 C6 123.9(3) . . ?
C7 N2 H2 118.0 . . ?
C6 N2 H2 118.0 . . ?
N4 N3 C7 116.8(3) . . ?
C8 N4 N3 117.3(3) . . ?
N6 N5 C8 117.1(3) . . ?
N5 N6 C7 117.2(2) . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.121
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1850387'
_audit_update_record             
;
2019-03-22 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H9 Cl Cu F12 N6 O4'
_chemical_formula_sum            'C18 H9 Cl Cu F12 N6 O4'
_chemical_formula_weight         700.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.9292(3)
_cell_length_b                   9.21150(10)
_cell_length_c                   17.4056(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.765(2)
_cell_angle_gamma                90
_cell_volume                     2500.30(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    6876
_cell_measurement_theta_min      4.1740
_cell_measurement_theta_max      72.2360

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_F_000             1380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.450
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova(Cu) micro-focus sealed X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_reflns_number            9887
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.430
_diffrn_reflns_theta_max         72.577
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4796
_reflns_number_gt                4434
_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+3.2996P] 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         4796
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.42052(16) 0.1326(3) 0.00209(14) 0.0272(5) Uani 1 1 d . . . . .
H1 H 0.471445 0.184733 0.008166 0.033 Uiso 1 1 calc R U . . .
C2 C 0.39001(17) 0.0637(3) -0.06837(14) 0.0320(5) Uani 1 1 d . . . . .
H2 H 0.420117 0.068115 -0.108809 0.038 Uiso 1 1 calc R U . . .
C3 C 0.31385(17) -0.0120(3) -0.07763(13) 0.0301(5) Uani 1 1 d . . . . .
H3 H 0.291662 -0.059335 -0.124588 0.036 Uiso 1 1 calc R U . . .
C4 C 0.27114(15) -0.0166(3) -0.01631(13) 0.0250(5) Uani 1 1 d . . . . .
H4 H 0.219491 -0.066427 -0.021739 0.030 Uiso 1 1 calc R U . . .
C5 C 0.30563(14) 0.0537(2) 0.05370(12) 0.0199(4) Uani 1 1 d . . . . .
C9 C 0.43885(15) 0.5286(2) 0.11185(13) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.52706(16) 0.5380(3) 0.12484(15) 0.0300(5) Uani 1 1 d . . . . .
H10 H 0.551852 0.629164 0.123856 0.036 Uiso 1 1 calc R U . . .
C11 C 0.58137(16) 0.4162(3) 0.13950(15) 0.0307(5) Uani 1 1 d . . . . .
C12 C 0.67810(18) 0.4491(3) 0.1600(2) 0.0460(7) Uani 1 1 d . . . . .
C13 C 0.38750(16) 0.6685(3) 0.09730(16) 0.0323(5) Uani 1 1 d . . . . .
C14 C 0.50686(15) 0.2969(3) 0.31959(13) 0.0246(5) Uani 1 1 d . . . . .
C15 C 0.53812(15) 0.1569(3) 0.33621(13) 0.0271(5) Uani 1 1 d . . . . .
H15 H 0.576097 0.137970 0.383251 0.033 Uiso 1 1 calc R U . . .
C16 C 0.51284(14) 0.0452(3) 0.28284(13) 0.0244(5) Uani 1 1 d . . . . .
C17 C 0.53947(17) -0.1103(3) 0.30743(15) 0.0315(5) Uani 1 1 d . . . . .
C18 C 0.53259(16) 0.4184(3) 0.38001(14) 0.0302(5) Uani 1 1 d . . . . .
F1 F 0.72471(13) 0.3410(3) 0.1480(2) 0.1000(11) Uani 1 1 d . . . . .
F2A F 0.70016(18) 0.5127(8) 0.2265(2) 0.110(2) Uani 0.803(8) 1 d . . P . .
F2B F 0.7076(8) 0.392(3) 0.2368(10) 0.110(2) Uani 0.197(8) 1 d . . P . .
F3 F 0.70056(15) 0.5520(3) 0.1139(2) 0.1111(12) Uani 1 1 d . . . . .
F4 F 0.34761(13) 0.69537(19) 0.15583(13) 0.0585(5) Uani 1 1 d . . . . .
F5 F 0.43392(10) 0.78595(16) 0.09007(11) 0.0429(4) Uani 1 1 d . . . . .
F6 F 0.32635(13) 0.6587(2) 0.03331(13) 0.0641(6) Uani 1 1 d . . . . .
F7 F 0.59912(13) -0.1175(2) 0.37201(10) 0.0557(5) Uani 1 1 d . . . . .
F8 F 0.57147(17) -0.1773(2) 0.25325(11) 0.0686(7) Uani 1 1 d . . . . .
F9 F 0.47322(14) -0.1837(2) 0.31953(19) 0.0896(9) Uani 1 1 d . . . . .
F10 F 0.57255(12) 0.36993(19) 0.44960(9) 0.0465(4) Uani 1 1 d . . . . .
F11 F 0.58488(11) 0.51170(19) 0.35454(10) 0.0438(4) Uani 1 1 d . . . . .
F12 F 0.46465(10) 0.49326(18) 0.39059(10) 0.0426(4) Uani 1 1 d . . . . .
O1 O 0.39075(10) 0.41888(17) 0.11026(9) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.56137(11) 0.28646(19) 0.13948(11) 0.0321(4) Uani 1 1 d . . . . .
O3 O 0.45778(11) 0.34179(18) 0.25824(9) 0.0278(4) Uani 1 1 d . . . . .
O4 O 0.46670(11) 0.05198(18) 0.21478(9) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.26254(15) 0.0441(2) 0.12307(13) 0.0242(5) Uani 1 1 d . . . . .
H6A H 0.201902 0.025503 0.104195 0.029 Uiso 1 1 calc R U . . .
H6B H 0.286349 -0.037572 0.155494 0.029 Uiso 1 1 calc R U . . .
C7 C 0.22819(14) 0.2972(2) 0.14464(13) 0.0216(4) Uani 1 1 d . . . . .
C8 C 0.16041(15) 0.5346(3) 0.09162(14) 0.0257(5) Uani 1 1 d . . . . .
CL1 Cl 0.12193(4) 0.69956(7) 0.05505(4) 0.03714(16) Uani 1 1 d . . . . .
CU1 Cu 0.42876(2) 0.23320(4) 0.16041(2) 0.02115(11) Uani 1 1 d . . . . .
N1 N 0.37960(12) 0.1274(2) 0.06232(10) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.27243(12) 0.1754(2) 0.17133(10) 0.0228(4) Uani 1 1 d . . . . .
H5 H 0.306300 0.175342 0.216644 0.027 Uiso 1 1 calc R U . . .
N3 N 0.19041(13) 0.3016(2) 0.06783(11) 0.0261(4) Uani 1 1 d . . . . .
N4 N 0.15544(13) 0.4264(2) 0.04057(11) 0.0286(4) Uani 1 1 d . . . . .
N5 N 0.22463(12) 0.4032(2) 0.19703(11) 0.0249(4) Uani 1 1 d . . . . .
N6 N 0.18961(13) 0.5271(2) 0.16903(11) 0.0261(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.343(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.341(3) . ?
C5 C6 1.508(3) . ?
C9 O1 1.265(3) . ?
C9 C10 1.380(3) . ?
C9 C13 1.520(3) . ?
C10 C11 1.408(4) . ?
C10 H10 0.9300 . ?
C11 O2 1.237(3) . ?
C11 C12 1.539(4) . ?
C12 F2A 1.281(5) . ?
C12 F1 1.285(4) . ?
C12 F3 1.337(4) . ?
C12 F2B 1.43(2) . ?
C13 F6 1.325(3) . ?
C13 F4 1.329(3) . ?
C13 F5 1.331(3) . ?
C14 O3 1.258(3) . ?
C14 C15 1.392(3) . ?
C14 C18 1.533(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 O4 1.262(3) . ?
C16 C17 1.531(3) . ?
C17 F9 1.306(3) . ?
C17 F8 1.314(3) . ?
C17 F7 1.317(3) . ?
C18 F10 1.325(3) . ?
C18 F12 1.328(3) . ?
C18 F11 1.334(3) . ?
F1 F2B 1.691(16) . ?
F2A F2B 1.13(3) . ?
O1 CU1 1.9593(16) . ?
O2 CU1 2.2691(18) . ?
O3 CU1 1.9476(16) . ?
O4 CU1 1.9529(16) . ?
C6 N2 1.463(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N5 1.345(3) . ?
C7 N3 1.350(3) . ?
C7 N2 1.355(3) . ?
C8 N4 1.327(3) . ?
C8 N6 1.335(3) . ?
C8 CL1 1.712(2) . ?
CU1 N1 1.9831(18) . ?
N2 H5 0.8600 . ?
N3 N4 1.322(3) . ?
N5 N6 1.320(3) . ?

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 122.6(2) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.6(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 121.0(2) . . ?
N1 C5 C6 118.23(19) . . ?
C4 C5 C6 120.7(2) . . ?
O1 C9 C10 130.2(2) . . ?
O1 C9 C13 111.8(2) . . ?
C10 C9 C13 118.0(2) . . ?
C9 C10 C11 123.2(2) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
O2 C11 C10 128.4(2) . . ?
O2 C11 C12 115.8(2) . . ?
C10 C11 C12 115.8(2) . . ?
F2A C12 F1 116.2(4) . . ?
F2A C12 F3 99.2(4) . . ?
F1 C12 F3 102.5(3) . . ?
F2A C12 F2B 49.1(9) . . ?
F1 C12 F2B 77.0(9) . . ?
F3 C12 F2B 138.5(8) . . ?
F2A C12 C11 112.1(3) . . ?
F1 C12 C11 113.2(2) . . ?
F3 C12 C11 112.2(3) . . ?
F2B C12 C11 105.5(6) . . ?
F6 C13 F4 105.8(2) . . ?
F6 C13 F5 107.7(2) . . ?
F4 C13 F5 106.4(2) . . ?
F6 C13 C9 111.1(2) . . ?
F4 C13 C9 110.8(2) . . ?
F5 C13 C9 114.5(2) . . ?
O3 C14 C15 128.0(2) . . ?
O3 C14 C18 112.1(2) . . ?
C15 C14 C18 120.0(2) . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O4 C16 C15 128.7(2) . . ?
O4 C16 C17 112.6(2) . . ?
C15 C16 C17 118.7(2) . . ?
F9 C17 F8 108.5(3) . . ?
F9 C17 F7 107.6(2) . . ?
F8 C17 F7 105.7(2) . . ?
F9 C17 C16 110.0(2) . . ?
F8 C17 C16 111.4(2) . . ?
F7 C17 C16 113.3(2) . . ?
F10 C18 F12 107.5(2) . . ?
F10 C18 F11 107.7(2) . . ?
F12 C18 F11 107.0(2) . . ?
F10 C18 C14 113.1(2) . . ?
F12 C18 C14 111.28(19) . . ?
F11 C18 C14 109.9(2) . . ?
C12 F1 F2B 55.2(9) . . ?
F2B F2A C12 72.1(8) . . ?
F2A F2B C12 58.8(13) . . ?
F2A F2B F1 99.0(16) . . ?
C12 F2B F1 47.8(5) . . ?
C9 O1 CU1 123.83(14) . . ?
C11 O2 CU1 117.19(16) . . ?
C14 O3 CU1 124.70(16) . . ?
C16 O4 CU1 124.09(16) . . ?
N2 C6 C5 113.45(18) . . ?
N2 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N5 C7 N3 125.3(2) . . ?
N5 C7 N2 117.34(19) . . ?
N3 C7 N2 117.4(2) . . ?
N4 C8 N6 126.8(2) . . ?
N4 C8 CL1 116.73(18) . . ?
N6 C8 CL1 116.47(18) . . ?
O3 CU1 O4 91.18(7) . . ?
O3 CU1 O1 86.44(7) . . ?
O4 CU1 O1 177.54(7) . . ?
O3 CU1 N1 170.69(8) . . ?
O4 CU1 N1 91.49(7) . . ?
O1 CU1 N1 90.77(7) . . ?
O3 CU1 O2 88.08(7) . . ?
O4 CU1 O2 93.23(7) . . ?
O1 CU1 O2 87.31(7) . . ?
N1 CU1 O2 100.67(7) . . ?
C5 N1 C1 119.05(19) . . ?
C5 N1 CU1 121.91(15) . . ?
C1 N1 CU1 119.02(16) . . ?
C7 N2 C6 119.99(18) . . ?
C7 N2 H5 120.0 . . ?
C6 N2 H5 120.0 . . ?
N4 N3 C7 116.85(19) . . ?
N3 N4 C8 116.70(19) . . ?
N6 N5 C7 116.80(19) . . ?
N5 N6 C8 116.83(19) . . ?

_refine_diff_density_max         0.896
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1850386'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl4 Cu N12, 2(C2 H3 N)'
_chemical_formula_sum            'C20 H20 Cl4 Cu N14'
_chemical_formula_weight         661.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   8.1726(7)
_cell_length_b                   8.7426(7)
_cell_length_c                   10.3892(8)
_cell_angle_alpha                82.662(7)
_cell_angle_beta                 67.773(8)
_cell_angle_gamma                79.566(7)
_cell_volume                     674.35(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    3709
_cell_measurement_theta_min      4.5830
_cell_measurement_theta_max      72.2250

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             335
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.140
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova(Cu) micro-focus sealed X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_reflns_number            4299
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.608
_diffrn_reflns_theta_max         72.694
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2546
_reflns_number_gt                2484
_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+0.9485P] 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         2546
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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 0.4004(3) 0.1942(3) 0.6049(3) 0.0113(5) Uani 1 1 d . . . . .
H1 H 0.481816 0.195207 0.647483 0.014 Uiso 1 1 calc R U . . .
C2 C 0.3149(3) 0.0659(3) 0.6306(3) 0.0136(5) Uani 1 1 d . . . . .
H2 H 0.337178 -0.017824 0.689430 0.016 Uiso 1 1 calc R U . . .
C3 C 0.1936(4) 0.0648(3) 0.5659(3) 0.0158(6) Uani 1 1 d . . . . .
H3 H 0.133463 -0.020329 0.580471 0.019 Uiso 1 1 calc R U . . .
C4 C 0.1641(3) 0.1920(3) 0.4799(3) 0.0129(5) Uani 1 1 d . . . . .
H4 H 0.083021 0.193691 0.436374 0.015 Uiso 1 1 calc R U . . .
C5 C 0.2558(3) 0.3169(3) 0.4586(3) 0.0080(5) Uani 1 1 d . . . . .
C6 C 0.2217(3) 0.4572(3) 0.3667(3) 0.0109(5) Uani 1 1 d . . . . .
H6A H 0.181139 0.424429 0.299436 0.013 Uiso 1 1 calc R U . . .
H6B H 0.126032 0.530705 0.423818 0.013 Uiso 1 1 calc R U . . .
C7 C 0.5161(4) 0.4712(3) 0.1833(3) 0.0098(5) Uani 1 1 d . . . . .
C8 C 0.7969(4) 0.3541(3) -0.0062(3) 0.0136(5) Uani 1 1 d . . . . .
C9 C 0.2220(8) 0.1131(5) 1.0926(5) 0.0528(12) Uani 1 1 d . . . . .
H9A H 0.324131 0.166920 1.051175 0.079 Uiso 1 1 calc R U . . .
H9B H 0.121400 0.182973 1.146762 0.079 Uiso 1 1 calc R U . . .
H9C H 0.195010 0.076653 1.020537 0.079 Uiso 1 1 calc R U . . .
C10 C 0.2603(4) -0.0179(3) 1.1816(3) 0.0199(6) Uani 1 1 d . . . . .
N1 N 0.3722(3) 0.3185(2) 0.5212(2) 0.0071(4) Uani 1 1 d . . . . .
N2 N 0.3768(3) 0.5368(2) 0.2917(2) 0.0090(4) Uani 1 1 d . . . . .
H7 H 0.380147 0.626094 0.316285 0.011 Uiso 1 1 calc R U . . .
N3 N 0.6794(3) 0.2586(3) 0.0671(2) 0.0153(5) Uani 1 1 d . . . . .
N4 N 0.5307(3) 0.3201(3) 0.1653(2) 0.0132(5) Uani 1 1 d . . . . .
N5 N 0.6282(3) 0.5706(3) 0.0984(2) 0.0148(5) Uani 1 1 d . . . . .
N6 N 0.7737(3) 0.5084(3) -0.0003(2) 0.0167(5) Uani 1 1 d . . . . .
N7 N 0.2859(4) -0.1210(3) 1.2525(3) 0.0256(6) Uani 1 1 d . . . . .
CL1 Cl 0.23433(7) 0.64031(7) 0.63301(6) 0.01075(18) Uani 1 1 d . . . . .
CL2 Cl 0.99038(9) 0.27642(9) -0.13068(7) 0.0230(2) Uani 1 1 d . . . . .
CU1 Cu 0.500000 0.500000 0.500000 0.00458(18) Uani 1 2 d S . P . .


_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 1.345(3) . ?
C1 C2 1.372(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.394(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.343(3) . ?
C5 C6 1.508(3) . ?
C6 N2 1.460(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N4 1.336(4) . ?
C7 N2 1.360(3) . ?
C7 N5 1.362(3) . ?
C8 N3 1.332(4) . ?
C8 N6 1.334(4) . ?
C8 CL2 1.709(3) . ?
C9 C10 1.444(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N7 1.130(4) . ?
N1 CU1 1.998(2) . ?
N2 H7 0.8600 . ?
N3 N4 1.331(3) . ?
N5 N6 1.322(3) . ?
CL1 CU1 2.3080(6) . ?
CU1 N1 1.998(2) 2_666 ?
CU1 CL1 2.3080(6) 2_666 ?

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 123.3(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 121.5(2) . . ?
N1 C5 C6 118.6(2) . . ?
C4 C5 C6 119.9(2) . . ?
N2 C6 C5 114.4(2) . . ?
N2 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
N2 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N4 C7 N2 119.4(2) . . ?
N4 C7 N5 125.3(2) . . ?
N2 C7 N5 115.3(2) . . ?
N3 C8 N6 126.5(3) . . ?
N3 C8 CL2 117.8(2) . . ?
N6 C8 CL2 115.6(2) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N7 C10 C9 178.2(4) . . ?
C5 N1 C1 118.5(2) . . ?
C5 N1 CU1 122.90(17) . . ?
C1 N1 CU1 118.55(17) . . ?
C7 N2 C6 120.7(2) . . ?
C7 N2 H7 119.6 . . ?
C6 N2 H7 119.6 . . ?
N4 N3 C8 117.1(2) . . ?
N3 N4 C7 116.6(2) . . ?
N6 N5 C7 116.9(2) . . ?
N5 N6 C8 116.7(2) . . ?
N1 CU1 N1 180.0 . 2_666 ?
N1 CU1 CL1 90.56(6) . 2_666 ?
N1 CU1 CL1 89.44(6) 2_666 2_666 ?
N1 CU1 CL1 89.44(6) . . ?
N1 CU1 CL1 90.56(6) 2_666 . ?
CL1 CU1 CL1 180.0 2_666 . ?

_refine_diff_density_max         0.725
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.154


####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1850385'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Cl3 Cu2 N12'
_chemical_formula_sum            'C16 H12 Cl3 Cu2 N12'
_chemical_formula_weight         605.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   13.5525(3)
_cell_length_b                   11.4392(2)
_cell_length_c                   13.7445(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.474(2)
_cell_angle_gamma                90
_cell_volume                     2063.18(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    5494
_cell_measurement_theta_min      3.3210
_cell_measurement_theta_max      73.3390

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_F_000             1204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    6.433
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova(Cu) micro-focus sealed X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_reflns_number            7939
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.368
_diffrn_reflns_theta_max         73.458
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4029
_reflns_number_gt                3648
_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.5969P] 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         4029
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0776
_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 0.41260(17) 0.7575(2) 0.05743(16) 0.0278(4) Uani 1 1 d . . . . .
H1 H 0.424930 0.702685 0.109020 0.033 Uiso 1 1 calc R U . . .
C2 C 0.31830(17) 0.8101(2) 0.03001(18) 0.0313(5) Uani 1 1 d . . . . .
H2 H 0.267803 0.791015 0.062301 0.038 Uiso 1 1 calc R U . . .
C3 C 0.30017(16) 0.8920(2) -0.04650(17) 0.0302(5) Uani 1 1 d . . . . .
H3 H 0.236870 0.928080 -0.066928 0.036 Uiso 1 1 calc R U . . .
C4 C 0.37671(16) 0.91939(19) -0.09204(16) 0.0270(4) Uani 1 1 d . . . . .
H4 H 0.366192 0.975312 -0.142708 0.032 Uiso 1 1 calc R U . . .
C5 C 0.46982(15) 0.86264(18) -0.06149(15) 0.0217(4) Uani 1 1 d . . . . .
C6 C 0.55466(15) 0.88897(18) -0.11044(15) 0.0227(4) Uani 1 1 d . . . . .
H6A H 0.534462 0.866056 -0.180569 0.027 Uiso 1 1 calc R U . . .
H6B H 0.567919 0.972389 -0.107529 0.027 Uiso 1 1 calc R U . . .
C7 C 0.73249(15) 0.85751(17) -0.07950(15) 0.0203(4) Uani 1 1 d . . . . .
C8 C 0.90611(16) 0.91469(19) -0.11123(15) 0.0237(4) Uani 1 1 d . . . . .
C9 C 1.04382(17) 0.6999(2) 0.14227(16) 0.0271(4) Uani 1 1 d . . . . .
H9 H 1.034765 0.780497 0.139141 0.032 Uiso 1 1 calc R U . . .
C10 C 1.14139(17) 0.6562(2) 0.17108(17) 0.0312(5) Uani 1 1 d . . . . .
H10 H 1.197082 0.705911 0.190835 0.037 Uiso 1 1 calc R U . . .
C11 C 1.15462(17) 0.5352(2) 0.16989(18) 0.0323(5) Uani 1 1 d . . . . .
H11 H 1.219688 0.503047 0.185075 0.039 Uiso 1 1 calc R U . . .
C12 C 1.06955(17) 0.4640(2) 0.14580(16) 0.0286(5) Uani 1 1 d . . . . .
H12 H 1.076882 0.383189 0.144507 0.034 Uiso 1 1 calc R U . . .
C13 C 0.97331(16) 0.51377(19) 0.12360(14) 0.0228(4) Uani 1 1 d . . . . .
C14 C 0.87840(16) 0.44074(18) 0.11001(16) 0.0258(4) Uani 1 1 d . . . . .
H14A H 0.874168 0.386250 0.055038 0.031 Uiso 1 1 calc R U . . .
H14B H 0.881379 0.395964 0.170607 0.031 Uiso 1 1 calc R U . . .
C15 C 0.70647(16) 0.48264(17) 0.11508(14) 0.0219(4) Uani 1 1 d . . . . .
C16 C 0.54511(16) 0.42818(19) 0.17352(15) 0.0251(4) Uani 1 1 d . . . . .
N1 N 0.48751(13) 0.78240(15) 0.01246(13) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.64671(13) 0.82689(15) -0.06051(13) 0.0214(3) Uani 1 1 d . . . . .
N3 N 0.73649(14) 0.94895(16) -0.14508(13) 0.0255(4) Uani 1 1 d . . . . .
N4 N 0.82510(14) 0.97773(16) -0.15955(13) 0.0254(4) Uani 1 1 d . . . . .
N5 N 0.90753(13) 0.82665(15) -0.04922(13) 0.0235(4) Uani 1 1 d . . . . .
N6 N 0.81859(13) 0.79709(15) -0.03239(13) 0.0213(3) Uani 1 1 d . . . . .
N7 N 0.62382(13) 0.55666(15) 0.09411(12) 0.0218(3) Uani 1 1 d . . . . .
N8 N 0.54203(13) 0.52728(15) 0.12527(13) 0.0237(4) Uani 1 1 d . . . . .
N9 N 0.62279(15) 0.34944(15) 0.19297(14) 0.0272(4) Uani 1 1 d . . . . .
N10 N 0.70310(14) 0.37574(15) 0.16244(13) 0.0256(4) Uani 1 1 d . . . . .
N11 N 0.78788(13) 0.51576(15) 0.08849(13) 0.0226(4) Uani 1 1 d . . . . .
N12 N 0.96104(13) 0.63068(16) 0.11846(13) 0.0233(4) Uani 1 1 d . . . . .
CL1 Cl 1.02182(4) 0.95597(5) -0.13079(4) 0.03246(14) Uani 1 1 d . . . . .
CL2 Cl 0.43963(4) 0.38980(5) 0.21467(4) 0.03062(13) Uani 1 1 d . . . . .
CL3 Cl 0.75441(4) 0.78814(4) 0.19329(4) 0.02720(12) Uani 1 1 d . . . . .
CU1 Cu 0.63246(2) 0.71372(3) 0.03952(2) 0.02047(9) Uani 1 1 d . . . . .
CU2 Cu 0.81393(2) 0.67687(3) 0.06595(2) 0.02200(10) 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 1.344(3) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.346(3) . ?
C5 C6 1.501(3) . ?
C6 N2 1.450(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.302(3) . ?
C7 N6 1.371(3) . ?
C7 N3 1.391(3) . ?
C8 N5 1.316(3) . ?
C8 N4 1.342(3) . ?
C8 CL1 1.722(2) . ?
C9 N12 1.345(3) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.395(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 N12 1.347(3) . ?
C13 C14 1.506(3) . ?
C14 N11 1.465(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N11 1.302(3) . ?
C15 N7 1.376(3) . ?
C15 N10 1.391(3) . ?
C16 N8 1.309(3) . ?
C16 N9 1.360(3) . ?
C16 CL2 1.721(2) . ?
N1 CU1 2.0614(18) . ?
N2 CU1 1.9329(17) . ?
N3 N4 1.307(2) . ?
N5 N6 1.327(2) . ?
N6 CU2 1.9404(17) . ?
N7 N8 1.328(2) . ?
N7 CU1 1.9618(17) . ?
N9 N10 1.296(3) . ?
N11 CU2 1.9163(17) . ?
N12 CU2 2.0139(18) . ?
CL3 CU2 2.4575(6) . ?
CL3 CU1 2.4853(6) . ?
CU1 CU2 2.4313(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 C2 122.5(2) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.63(19) . . ?
N1 C5 C6 117.62(17) . . ?
C4 C5 C6 120.75(19) . . ?
N2 C6 C5 110.76(16) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 N6 117.83(18) . . ?
N2 C7 N3 120.93(18) . . ?
N6 C7 N3 121.24(18) . . ?
N5 C8 N4 127.53(19) . . ?
N5 C8 CL1 116.38(16) . . ?
N4 C8 CL1 116.07(16) . . ?
N12 C9 C10 122.6(2) . . ?
N12 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C9 C10 C11 118.3(2) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
N12 C13 C12 121.1(2) . . ?
N12 C13 C14 116.99(18) . . ?
C12 C13 C14 121.80(19) . . ?
N11 C14 C13 110.25(17) . . ?
N11 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N11 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N11 C15 N7 117.68(18) . . ?
N11 C15 N10 121.07(19) . . ?
N7 C15 N10 121.25(19) . . ?
N8 C16 N9 126.7(2) . . ?
N8 C16 CL2 117.62(17) . . ?
N9 C16 CL2 115.61(16) . . ?
C1 N1 C5 118.63(18) . . ?
C1 N1 CU1 129.15(15) . . ?
C5 N1 CU1 112.21(13) . . ?
C7 N2 C6 118.62(17) . . ?
C7 N2 CU1 125.17(14) . . ?
C6 N2 CU1 115.94(13) . . ?
N4 N3 C7 118.30(17) . . ?
N3 N4 C8 117.27(17) . . ?
C8 N5 N6 116.17(17) . . ?
N5 N6 C7 119.48(17) . . ?
N5 N6 CU2 119.43(13) . . ?
C7 N6 CU2 120.94(14) . . ?
N8 N7 C15 118.57(17) . . ?
N8 N7 CU1 119.32(13) . . ?
C15 N7 CU1 121.36(14) . . ?
C16 N8 N7 117.34(18) . . ?
N10 N9 C16 117.00(18) . . ?
N9 N10 C15 118.93(18) . . ?
C15 N11 C14 119.88(17) . . ?
C15 N11 CU2 121.89(14) . . ?
C14 N11 CU2 114.65(13) . . ?
C9 N12 C13 119.14(19) . . ?
C9 N12 CU2 128.59(15) . . ?
C13 N12 CU2 112.17(14) . . ?
CU2 CL3 CU1 58.926(14) . . ?
N2 CU1 N7 155.72(7) . . ?
N2 CU1 N1 82.91(7) . . ?
N7 CU1 N1 105.83(7) . . ?
N2 CU1 CU2 86.86(5) . . ?
N7 CU1 CU2 86.50(5) . . ?
N1 CU1 CU2 167.36(5) . . ?
N2 CU1 CL3 102.24(5) . . ?
N7 CU1 CL3 94.53(5) . . ?
N1 CU1 CL3 115.09(5) . . ?
CU2 CU1 CL3 59.966(15) . . ?
N11 CU2 N6 146.48(7) . . ?
N11 CU2 N12 84.01(7) . . ?
N6 CU2 N12 103.53(7) . . ?
N11 CU2 CU1 88.31(5) . . ?
N6 CU2 CU1 88.90(5) . . ?
N12 CU2 CU1 166.62(5) . . ?
N11 CU2 CL3 106.05(5) . . ?
N6 CU2 CL3 101.69(5) . . ?
N12 CU2 CL3 110.64(5) . . ?
CU1 CU2 CL3 61.108(15) . . ?

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.074



####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1850388'
_audit_update_record             
;
2019-03-22 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 Cl2 Cu2 F3 N12 O3 S'
_chemical_formula_sum            'C17 H12 Cl2 Cu2 F3 N12 O3 S'
_chemical_formula_weight         719.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   15.3612(4)
_cell_length_b                   10.9054(3)
_cell_length_c                   15.4148(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.358(4)
_cell_angle_gamma                90
_cell_volume                     2404.94(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    5742
_cell_measurement_theta_min      3.0680
_cell_measurement_theta_max      73.3500

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_F_000             1428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    5.723
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova(Cu) micro-focus sealed X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_reflns_number            9791
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.089
_diffrn_reflns_theta_max         73.448
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4706
_reflns_number_gt                4183
_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0741P)²+8.8657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4706
_refine_ls_number_parameters     416
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.2411(3) 0.6050(4) 0.1376(3) 0.0332(10) Uani 1 1 d . . . . .
H1 H 0.182699 0.580234 0.096434 0.040 Uiso 1 1 calc R U . . .
C2 C 0.2751(4) 0.7166(5) 0.1237(4) 0.0439(12) Uani 1 1 d . . . . .
H2 H 0.241008 0.766002 0.073653 0.053 Uiso 1 1 calc R U . . .
C3 C 0.3618(3) 0.7541(5) 0.1863(4) 0.0416(12) Uani 1 1 d . . . . .
H3 H 0.385820 0.830335 0.179839 0.050 Uiso 1 1 calc R U . . .
C4 C 0.4118(3) 0.6769(4) 0.2582(3) 0.0333(10) Uani 1 1 d . . . . .
H4 H 0.470377 0.699886 0.299917 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3735(3) 0.5645(4) 0.2675(3) 0.0254(8) Uani 1 1 d . . . . .
C6 C 0.4252(3) 0.4750(4) 0.3425(3) 0.0269(8) Uani 1 1 d . . . . .
H6A H 0.485099 0.455655 0.338213 0.032 Uiso 1 1 calc R U . . .
H6B H 0.436493 0.511114 0.403161 0.032 Uiso 1 1 calc R U . . .
C7A C 0.4031(3) 0.2757(5) 0.3943(4) 0.0210(9) Uani 0.810(3) 1 d . . P A 1
C7B C 0.4229(16) 0.267(2) 0.3624(16) 0.0210(9) Uani 0.190(3) 1 d . . P A 2
C8A C 0.4524(4) 0.1239(4) 0.5311(3) 0.0247(10) Uani 0.810(3) 1 d . . P A 1
C8B C 0.5182(13) 0.0653(16) 0.4073(15) 0.019(4) Uani 0.190(3) 1 d . U P A 2
C9 C 0.2591(3) -0.1250(4) 0.3513(3) 0.0276(9) Uani 1 1 d . . . . .
H9 H 0.317039 -0.102847 0.394768 0.033 Uiso 1 1 calc R U . . .
C10 C 0.2313(3) -0.2454(4) 0.3473(3) 0.0355(10) Uani 1 1 d . . . . .
H10 H 0.269574 -0.303599 0.387332 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1453(4) -0.2783(4) 0.2825(4) 0.0380(10) Uani 1 1 d . . . . .
H11 H 0.125007 -0.359195 0.277855 0.046 Uiso 1 1 calc R U . . .
C12 C 0.0900(3) -0.1893(4) 0.2249(3) 0.0325(9) Uani 1 1 d . . . . .
H12 H 0.031769 -0.209600 0.181100 0.039 Uiso 1 1 calc R U . . .
C13 C 0.1219(3) -0.0697(4) 0.2328(3) 0.0279(9) Uani 1 1 d . . . . .
C14 C 0.0636(3) 0.0295(4) 0.1723(4) 0.0363(10) Uani 1 1 d . . . . .
H14A H 0.051655 0.010921 0.107421 0.044 Uiso 1 1 calc R U . . .
H14B H 0.004001 0.034230 0.180466 0.044 Uiso 1 1 calc R U . . .
C15 C 0.0697(3) 0.2446(4) 0.1530(3) 0.0278(8) Uani 1 1 d . . . . .
C16 C -0.0224(3) 0.4447(4) 0.0975(3) 0.0271(8) Uani 1 1 d . . . . .
C17 C 0.2023(4) 0.0906(6) -0.0081(4) 0.0513(14) Uani 1 1 d . . . . .
CL1A Cl 0.48145(9) 0.03558(12) 0.62955(8) 0.0311(4) Uani 0.810(3) 1 d . . P A 1
CL1B Cl 0.5883(3) -0.0612(5) 0.4248(4) 0.0310(15) Uani 0.190(3) 1 d . . P A 2
CL2 Cl -0.08896(7) 0.57599(10) 0.06939(8) 0.0350(3) Uani 1 1 d . . . . .
CU1 Cu 0.25036(4) 0.36101(5) 0.23701(4) 0.02284(18) Uani 1 1 d . . . . .
CU2A Cu 0.2370(3) 0.1417(4) 0.2865(2) 0.0215(5) Uani 0.810(3) 1 d . . P A 1
CU2B Cu 0.2418(12) 0.1442(17) 0.2653(8) 0.022(2) Uani 0.190(3) 1 d . . P A 2
N1 N 0.2885(2) 0.5296(3) 0.2083(2) 0.0247(7) Uani 1 1 d . . . . .
N2 N 0.3702(2) 0.3635(3) 0.3321(3) 0.0278(8) Uani 1 1 d . . . . .
N3A N 0.4947(3) 0.2806(5) 0.4583(3) 0.0227(10) Uani 0.810(3) 1 d . . P A 1
N3B N 0.5097(18) 0.269(3) 0.4338(17) 0.0227(10) Uani 0.190(3) 1 d . . P A 2
N4A N 0.5186(3) 0.2045(4) 0.5275(3) 0.0259(9) Uani 0.810(3) 1 d . . P A 1
N4B N 0.5573(10) 0.1696(16) 0.4540(12) 0.022(4) Uani 0.190(3) 1 d . . P A 2
N5A N 0.3490(3) 0.1740(4) 0.3900(3) 0.0228(8) Uani 0.810(3) 1 d . . P A 1
N5B N 0.3789(12) 0.1526(15) 0.3384(13) 0.0228(8) Uani 0.190(3) 1 d . . P A 2
N6A N 0.3732(3) 0.0991(4) 0.4627(3) 0.0246(9) Uani 0.810(3) 1 d . . P A 1
N6B N 0.4308(11) 0.0515(16) 0.3575(14) 0.026(4) Uani 0.190(3) 1 d . . P A 2
N7 N 0.1162(2) 0.3551(3) 0.1746(3) 0.0266(7) Uani 1 1 d . . . . .
N8 N 0.0669(2) 0.4577(3) 0.1499(2) 0.0268(7) Uani 1 1 d . . . . .
N9 N -0.0173(3) 0.2386(3) 0.0814(3) 0.0336(8) Uani 1 1 d . . . . .
N10 N -0.0637(2) 0.3407(4) 0.0559(3) 0.0313(8) Uani 1 1 d . . . . .
N11 N 0.1122(2) 0.1474(3) 0.1968(3) 0.0294(8) Uani 1 1 d . . . . .
N12 N 0.2059(2) -0.0383(3) 0.2950(3) 0.0264(7) Uani 1 1 d . . . . .
O1 O 0.2646(3) 0.2719(3) 0.1024(2) 0.0429(8) Uani 1 1 d . . . . .
O2 O 0.2996(3) 0.0689(4) 0.1693(3) 0.0509(9) Uani 1 1 d . . . . .
O3 O 0.3767(2) 0.1426(4) 0.0655(3) 0.0509(10) Uani 1 1 d . . . . .
S1 S 0.29756(8) 0.15077(10) 0.09435(8) 0.0326(3) Uani 1 1 d . . . . .
F1 F 0.1945(2) 0.1532(3) -0.08031(19) 0.0417(7) Uani 1 1 d . . . . .
F2 F 0.1210(3) 0.0948(5) 0.0024(3) 0.0890(16) Uani 1 1 d . . . . .
F3 F 0.2206(4) -0.0235(4) -0.0257(4) 0.0986(16) 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 1.348(5) . ?
C1 C2 1.372(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.347(5) . ?
C5 C6 1.499(6) . ?
C6 N2 1.456(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7A N2 1.318(6) . ?
C7A N5A 1.373(6) . ?
C7A N3A 1.394(7) . ?
C7B N2 1.31(2) . ?
C7B N3B 1.39(3) . ?
C7B N5B 1.40(3) . ?
C8A N6A 1.317(7) . ?
C8A N4A 1.360(7) . ?
C8A CL1A 1.713(5) . ?
C8B N6B 1.29(3) . ?
C8B N4B 1.36(3) . ?
C8B CL1B 1.710(18) . ?
C9 N12 1.341(6) . ?
C9 C10 1.376(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(6) . ?
C12 H12 0.9300 . ?
C13 N12 1.342(5) . ?
C13 C14 1.495(6) . ?
C14 N11 1.465(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N11 1.297(6) . ?
C15 N7 1.379(5) . ?
C15 N9 1.391(6) . ?
C16 N8 1.322(5) . ?
C16 N10 1.343(6) . ?
C16 CL2 1.720(4) . ?
C17 F1 1.273(7) . ?
C17 F2 1.318(7) . ?
C17 F3 1.325(7) . ?
C17 S1 1.839(6) . ?
CU1 N2 1.890(3) . ?
CU1 N7 1.931(4) . ?
CU1 N1 2.027(4) . ?
CU1 O1 2.372(3) . ?
CU1 CU2B 2.416(18) . ?
CU1 CU2A 2.541(4) . ?
CU2A N5A 1.906(6) . ?
CU2A N11 1.913(5) . ?
CU2A N12 2.036(5) . ?
CU2B N11 1.884(17) . ?
CU2B N5B 2.00(2) . ?
CU2B O2 2.147(15) . ?
CU2B N12 2.159(18) . ?
N3A N4A 1.296(7) . ?
N3B N4B 1.28(3) . ?
N5A N6A 1.325(6) . ?
N5B N6B 1.33(2) . ?
N7 N8 1.328(5) . ?
N9 N10 1.303(5) . ?
O1 S1 1.436(4) . ?
O2 S1 1.451(4) . ?
O3 S1 1.441(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 C2 122.9(4) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.3(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.4(4) . . ?
N1 C5 C6 116.7(4) . . ?
C4 C5 C6 121.9(4) . . ?
N2 C6 C5 109.6(3) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7A N5A 119.1(4) . . ?
N2 C7A N3A 120.5(4) . . ?
N5A C7A N3A 120.1(4) . . ?
N2 C7B N3B 124(2) . . ?
N2 C7B N5B 116.4(17) . . ?
N3B C7B N5B 117(2) . . ?
N6A C8A N4A 125.9(4) . . ?
N6A C8A CL1A 117.4(4) . . ?
N4A C8A CL1A 116.2(4) . . ?
N6B C8B N4B 125.1(16) . . ?
N6B C8B CL1B 117.3(15) . . ?
N4B C8B CL1B 117.3(14) . . ?
N12 C9 C10 122.5(4) . . ?
N12 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C9 C10 C11 118.7(4) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
N12 C13 C12 121.4(4) . . ?
N12 C13 C14 117.6(4) . . ?
C12 C13 C14 121.0(4) . . ?
N11 C14 C13 110.0(3) . . ?
N11 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
N11 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
N11 C15 N7 118.0(4) . . ?
N11 C15 N9 122.0(4) . . ?
N7 C15 N9 119.7(4) . . ?
N8 C16 N10 125.9(4) . . ?
N8 C16 CL2 117.0(3) . . ?
N10 C16 CL2 116.6(3) . . ?
F1 C17 F2 107.3(6) . . ?
F1 C17 F3 106.5(5) . . ?
F2 C17 F3 109.7(5) . . ?
F1 C17 S1 110.6(4) . . ?
F2 C17 S1 112.0(4) . . ?
F3 C17 S1 110.5(5) . . ?
N2 CU1 N7 161.34(17) . . ?
N2 CU1 N1 83.05(14) . . ?
N7 CU1 N1 105.23(14) . . ?
N2 CU1 O1 108.10(15) . . ?
N7 CU1 O1 88.40(15) . . ?
N1 CU1 O1 93.14(13) . . ?
N2 CU1 CU2B 88.6(4) . . ?
N7 CU1 CU2B 86.5(4) . . ?
N1 CU1 CU2B 165.0(4) . . ?
O1 CU1 CU2B 77.6(3) . . ?
N2 CU1 CU2A 86.74(14) . . ?
N7 CU1 CU2A 85.96(14) . . ?
N1 CU1 CU2A 168.69(14) . . ?
O1 CU1 CU2A 85.42(11) . . ?
N5A CU2A N11 163.9(3) . . ?
N5A CU2A N12 106.6(2) . . ?
N11 CU2A N12 83.2(2) . . ?
N5A CU2A CU1 85.99(19) . . ?
N11 CU2A CU1 85.51(17) . . ?
N12 CU2A CU1 166.8(2) . . ?
N11 CU2B N5B 176.3(12) . . ?
N11 CU2B O2 103.8(6) . . ?
N5B CU2B O2 77.9(8) . . ?
N11 CU2B N12 80.6(6) . . ?
N5B CU2B N12 102.8(9) . . ?
O2 CU2B N12 89.7(7) . . ?
N11 CU2B CU1 89.8(7) . . ?
N5B CU2B CU1 86.6(8) . . ?
O2 CU2B CU1 100.8(5) . . ?
N12 CU2B CU1 167.2(8) . . ?
C5 N1 C1 118.8(4) . . ?
C5 N1 CU1 113.2(3) . . ?
C1 N1 CU1 128.0(3) . . ?
C7B N2 C6 112.0(10) . . ?
C7A N2 C6 118.2(4) . . ?
C7B N2 CU1 124.5(10) . . ?
C7A N2 CU1 124.1(3) . . ?
C6 N2 CU1 117.3(3) . . ?
N4A N3A C7A 117.9(5) . . ?
N4B N3B C7B 118(2) . . ?
N3A N4A C8A 117.2(4) . . ?
N3B N4B C8B 118.4(18) . . ?
N6A N5A C7A 118.6(4) . . ?
N6A N5A CU2A 118.9(3) . . ?
C7A N5A CU2A 122.4(3) . . ?
N6B N5B C7B 119.0(17) . . ?
N6B N5B CU2B 120.8(14) . . ?
C7B N5B CU2B 119.9(15) . . ?
C8A N6A N5A 116.3(4) . . ?
C8B N6B N5B 116.5(16) . . ?
N8 N7 C15 118.4(3) . . ?
N8 N7 CU1 120.6(3) . . ?
C15 N7 CU1 121.0(3) . . ?
C16 N8 N7 116.3(4) . . ?
N10 N9 C15 117.5(4) . . ?
N9 N10 C16 117.8(3) . . ?
C15 N11 C14 118.0(4) . . ?
C15 N11 CU2B 122.4(6) . . ?
C14 N11 CU2B 117.6(6) . . ?
C15 N11 CU2A 125.8(3) . . ?
C14 N11 CU2A 116.1(3) . . ?
C9 N12 C13 118.9(4) . . ?
C9 N12 CU2A 128.3(3) . . ?
C13 N12 CU2A 112.8(3) . . ?
C9 N12 CU2B 130.2(5) . . ?
C13 N12 CU2B 109.7(5) . . ?
S1 O1 CU1 126.9(2) . . ?
S1 O2 CU2B 114.7(5) . . ?
O1 S1 O3 116.6(2) . . ?
O1 S1 O2 113.7(2) . . ?
O3 S1 O2 115.5(2) . . ?
O1 S1 C17 102.0(3) . . ?
O3 S1 C17 102.1(3) . . ?
O2 S1 C17 104.1(3) . . ?

_refine_diff_density_max         1.401
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.121

