# 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_CuSKMa10z
_database_code_depnum_ccdc_archive 'CCDC 1914390'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Choroba'
;University of Silesia
Poland
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 Cl2 Cu N4'
_chemical_formula_sum            'C24 H16 Cl2 Cu N4'
_chemical_formula_weight         494.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.7287(3)
_cell_length_b                   14.2823(7)
_cell_length_c                   18.7465(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.268(4)
_cell_angle_gamma                90
_cell_volume                     2052.68(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2967
_cell_measurement_theta_min      3.9040
_cell_measurement_theta_max      28.9740

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             1004
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.345
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84831
_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            9696
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.322
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3624
_reflns_number_gt                2911
_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)+(0.0351P)²+0.5386P] 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         3624
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
Cu1 Cu 0.09542(4) 0.61667(2) 0.05031(2) 0.03103(12) Uani 1 1 d . . . . .
Cl1 Cl 0.27420(9) 0.49599(5) 0.07676(4) 0.0496(2) Uani 1 1 d . . . . .
Cl2 Cl 0.23737(7) 0.75117(5) 0.12361(3) 0.03554(17) Uani 1 1 d . . . . .
N1 N -0.0733(2) 0.59288(15) 0.12430(11) 0.0308(5) Uani 1 1 d . . . . .
N2 N -0.1030(2) 0.69267(14) 0.00958(10) 0.0265(5) Uani 1 1 d . . . . .
N3 N 0.1690(2) 0.65412(16) -0.04757(10) 0.0317(5) Uani 1 1 d . . . . .
N4 N -0.4791(3) 0.94203(15) -0.11361(10) 0.0319(5) Uani 1 1 d . . . . .
C1 C -0.0434(3) 0.5421(2) 0.18443(15) 0.0417(7) Uani 1 1 d . . . . .
H1 H 0.0592 0.5076 0.1929 0.050 Uiso 1 1 calc R U . . .
C2 C -0.1597(4) 0.5392(2) 0.23426(15) 0.0473(7) Uani 1 1 d . . . . .
H2 H -0.1349 0.5043 0.2762 0.057 Uiso 1 1 calc R U . . .
C3 C -0.3132(4) 0.5887(2) 0.22118(15) 0.0432(7) Uani 1 1 d . . . . .
H3 H -0.3934 0.5877 0.2542 0.052 Uiso 1 1 calc R U . . .
C4 C -0.3467(3) 0.63946(19) 0.15889(13) 0.0343(6) Uani 1 1 d . . . . .
H4 H -0.4515 0.6716 0.1484 0.041 Uiso 1 1 calc R U . . .
C5 C -0.2232(3) 0.64225(18) 0.11208(12) 0.0277(6) Uani 1 1 d . . . . .
C6 C -0.2389(3) 0.70035(18) 0.04653(12) 0.0264(5) Uani 1 1 d . . . . .
C7 C -0.3736(3) 0.76152(18) 0.02425(12) 0.0293(6) Uani 1 1 d . . . . .
H7 H -0.4685 0.7662 0.0500 0.035 Uiso 1 1 calc R U . . .
C8 C -0.3663(3) 0.81592(18) -0.03678(12) 0.0271(5) Uani 1 1 d . . . . .
C9 C -0.2243(3) 0.80394(18) -0.07532(12) 0.0292(6) Uani 1 1 d . . . . .
H9 H -0.2168 0.8384 -0.1169 0.035 Uiso 1 1 calc R U . . .
C10 C -0.0952(3) 0.74056(18) -0.05109(12) 0.0280(6) Uani 1 1 d . . . . .
C11 C 0.0612(3) 0.71565(19) -0.08569(12) 0.0291(6) Uani 1 1 d . . . . .
C12 C 0.0962(3) 0.7495(2) -0.15130(13) 0.0390(7) Uani 1 1 d . . . . .
H12 H 0.0206 0.7918 -0.1769 0.047 Uiso 1 1 calc R U . . .
C13 C 0.2449(3) 0.7198(2) -0.17851(14) 0.0458(8) Uani 1 1 d . . . . .
H13 H 0.2705 0.7415 -0.2228 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3541(3) 0.6580(2) -0.13928(14) 0.0459(8) Uani 1 1 d . . . . .
H14 H 0.4555 0.6378 -0.1565 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3128(3) 0.6262(2) -0.07431(14) 0.0385(7) Uani 1 1 d . . . . .
H15 H 0.3872 0.5839 -0.0481 0.046 Uiso 1 1 calc R U . . .
C16 C -0.5046(3) 0.88603(18) -0.05985(12) 0.0271(5) Uani 1 1 d . . . . .
C17 C -0.6549(3) 0.89163(19) -0.02415(14) 0.0348(6) Uani 1 1 d . . . . .
H17 H -0.6678 0.8521 0.0143 0.042 Uiso 1 1 calc R U . . .
C18 C -0.7799(3) 0.9554(2) -0.04675(14) 0.0378(6) Uani 1 1 d . . . . .
H18 H -0.8801 0.9588 -0.0241 0.045 Uiso 1 1 calc R U . . .
C19 C -0.7599(3) 1.01612(18) -0.10351(13) 0.0298(6) Uani 1 1 d . . . . .
C20 C -0.6039(3) 1.00744(18) -0.13555(13) 0.0315(6) Uani 1 1 d . . . . .
C21 C -0.5758(4) 1.0698(2) -0.19135(15) 0.0464(7) Uani 1 1 d . . . . .
H21 H -0.4723 1.0669 -0.2117 0.056 Uiso 1 1 calc R U . . .
C22 C -0.6998(4) 1.1343(2) -0.21565(15) 0.0489(8) Uani 1 1 d . . . . .
H22 H -0.6813 1.1739 -0.2533 0.059 Uiso 1 1 calc R U . . .
C23 C -0.8545(4) 1.1414(2) -0.18445(14) 0.0403(7) Uani 1 1 d . . . . .
H23 H -0.9382 1.1853 -0.2017 0.048 Uiso 1 1 calc R U . . .
C24 C -0.8828(3) 1.08491(19) -0.12966(14) 0.0360(6) Uani 1 1 d . . . . .
H24 H -0.9849 1.0913 -0.1087 0.043 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
Cu1 N2 1.9536(19) . ?
Cu1 N1 2.049(2) . ?
Cu1 N3 2.059(2) . ?
Cu1 Cl1 2.2254(7) . ?
Cu1 Cl2 2.5300(7) . ?
N1 C1 1.335(3) . ?
N1 C5 1.351(3) . ?
N2 C6 1.334(3) . ?
N2 C10 1.335(3) . ?
N3 C15 1.337(3) . ?
N3 C11 1.351(3) . ?
N4 C16 1.321(3) . ?
N4 C20 1.368(3) . ?
C1 C2 1.376(4) . ?
C2 C3 1.375(4) . ?
C3 C4 1.371(4) . ?
C4 C5 1.377(3) . ?
C5 C6 1.475(3) . ?
C6 C7 1.382(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.399(3) . ?
C8 C16 1.488(3) . ?
C9 C10 1.380(3) . ?
C10 C11 1.486(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.382(4) . ?
C13 C14 1.369(4) . ?
C14 C15 1.375(4) . ?
C16 C17 1.414(3) . ?
C17 C18 1.356(4) . ?
C18 C19 1.396(4) . ?
C19 C24 1.410(3) . ?
C19 C20 1.419(3) . ?
C20 C21 1.411(4) . ?
C21 C22 1.366(4) . ?
C22 C23 1.399(4) . ?
C23 C24 1.345(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
N2 Cu1 N1 79.71(8) . . ?
N2 Cu1 N3 78.39(8) . . ?
N1 Cu1 N3 156.56(8) . . ?
N2 Cu1 Cl1 162.16(6) . . ?
N1 Cu1 Cl1 98.69(6) . . ?
N3 Cu1 Cl1 99.56(6) . . ?
N2 Cu1 Cl2 93.18(6) . . ?
N1 Cu1 Cl2 91.58(6) . . ?
N3 Cu1 Cl2 97.89(6) . . ?
Cl1 Cu1 Cl2 104.64(3) . . ?
C1 N1 C5 118.7(2) . . ?
C1 N1 Cu1 127.20(17) . . ?
C5 N1 Cu1 113.84(16) . . ?
C6 N2 C10 121.6(2) . . ?
C6 N2 Cu1 118.25(16) . . ?
C10 N2 Cu1 120.01(15) . . ?
C15 N3 C11 118.8(2) . . ?
C15 N3 Cu1 126.37(18) . . ?
C11 N3 Cu1 114.78(16) . . ?
C16 N4 C20 118.4(2) . . ?
N1 C1 C2 122.1(2) . . ?
C3 C2 C1 119.1(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 C5 119.1(2) . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 C6 114.4(2) . . ?
C4 C5 C6 123.8(2) . . ?
N2 C6 C7 120.5(2) . . ?
N2 C6 C5 113.5(2) . . ?
C7 C6 C5 125.9(2) . . ?
C6 C7 C8 119.7(2) . . ?
C7 C8 C9 118.2(2) . . ?
C7 C8 C16 120.9(2) . . ?
C9 C8 C16 120.9(2) . . ?
C10 C9 C8 119.5(2) . . ?
N2 C10 C9 120.5(2) . . ?
N2 C10 C11 112.1(2) . . ?
C9 C10 C11 127.4(2) . . ?
N3 C11 C12 121.5(2) . . ?
N3 C11 C10 113.9(2) . . ?
C12 C11 C10 124.6(2) . . ?
C11 C12 C13 119.2(3) . . ?
C14 C13 C12 119.0(3) . . ?
C13 C14 C15 119.5(3) . . ?
N3 C15 C14 122.1(3) . . ?
N4 C16 C17 122.5(2) . . ?
N4 C16 C8 117.3(2) . . ?
C17 C16 C8 120.2(2) . . ?
C18 C17 C16 119.0(2) . . ?
C17 C18 C19 120.8(2) . . ?
C18 C19 C24 124.3(2) . . ?
C18 C19 C20 116.7(2) . . ?
C24 C19 C20 119.0(2) . . ?
N4 C20 C21 119.0(2) . . ?
N4 C20 C19 122.5(2) . . ?
C21 C20 C19 118.5(2) . . ?
C22 C21 C20 120.4(3) . . ?
C21 C22 C23 120.7(3) . . ?
C24 C23 C22 120.4(3) . . ?
C23 C24 C19 121.0(3) . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.062

_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_cu209
_database_code_depnum_ccdc_archive 'CCDC 1914394'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Choroba'
;University of Silesia
Poland
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cl2 Cu N6, H2 O'
_chemical_formula_sum            'C22 H16 Cl2 Cu N6 O'
_chemical_formula_weight         514.85

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   13.4958(6)
_cell_length_b                   12.6508(6)
_cell_length_c                   25.5678(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.202(5)
_cell_angle_gamma                90
_cell_volume                     4282.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4212
_cell_measurement_theta_min      3.7210
_cell_measurement_theta_max      28.4370

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             2088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.298
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78333
_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            9458
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.429
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3771
_reflns_number_gt                3135
_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)+(0.0361P)²+8.3792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Cu1 Cu 0.15309(3) 0.80583(3) 0.35048(2) 0.03634(13) Uani 1 1 d . . . . .
Cl1 Cl 0.10086(7) 0.89560(7) 0.27567(3) 0.0546(2) Uani 1 1 d . . . . .
Cl2 Cl 0.33848(6) 0.84639(7) 0.37100(3) 0.0466(2) Uani 1 1 d . . . . .
N1 N 0.15666(18) 0.65704(19) 0.31948(9) 0.0343(5) Uani 1 1 d . . . . .
N2 N 0.13793(17) 0.71849(18) 0.41184(9) 0.0317(5) Uani 1 1 d . . . . .
N3 N 0.1270(2) 0.9188(2) 0.40352(10) 0.0433(6) Uani 1 1 d . . . . .
N4 N 0.1577(2) 0.4470(2) 0.28838(10) 0.0462(7) Uani 1 1 d . . . . .
N5 N 0.1165(3) 1.0568(2) 0.48662(13) 0.0665(9) Uani 1 1 d . . . . .
N6 N 0.12637(17) 0.42851(19) 0.54050(9) 0.0351(5) Uani 1 1 d . . . . .
C1 C 0.1654(2) 0.6306(3) 0.27022(11) 0.0430(7) Uani 1 1 d . . . . .
H1 H 0.171086 0.683283 0.245589 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1660(3) 0.5257(3) 0.25531(12) 0.0491(8) Uani 1 1 d . . . . .
H2 H 0.172556 0.509670 0.220647 0.059 Uiso 1 1 calc R U . . .
C3 C 0.1498(2) 0.4741(2) 0.33795(11) 0.0382(7) Uani 1 1 d . . . . .
H3 H 0.144179 0.421152 0.362413 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1497(2) 0.5780(2) 0.35390(10) 0.0312(6) Uani 1 1 d . . . . .
C5 C 0.14026(19) 0.6129(2) 0.40806(10) 0.0304(6) Uani 1 1 d . . . . .
C6 C 0.1327(2) 0.5498(2) 0.45136(11) 0.0333(6) Uani 1 1 d . . . . .
H6 H 0.135221 0.476579 0.448722 0.040 Uiso 1 1 calc R U . . .
C7 C 0.12105(19) 0.5979(2) 0.49929(10) 0.0318(6) Uani 1 1 d . . . . .
C8 C 0.1171(2) 0.7077(2) 0.50153(11) 0.0355(7) Uani 1 1 d . . . . .
H8 H 0.108397 0.741491 0.532644 0.043 Uiso 1 1 calc R U . . .
C9 C 0.1261(2) 0.7659(2) 0.45712(11) 0.0334(6) Uani 1 1 d . . . . .
C10 C 0.1237(2) 0.8821(2) 0.45270(11) 0.0375(7) Uani 1 1 d . . . . .
C11 C 0.1184(3) 0.9519(3) 0.49362(13) 0.0514(8) Uani 1 1 d . . . . .
H11 H 0.115961 0.925043 0.527216 0.062 Uiso 1 1 calc R U . A 1
C12 C 0.1192(3) 1.0897(3) 0.43804(17) 0.0725(12) Uani 1 1 d . . . . .
H12 H 0.117191 1.162128 0.431618 0.087 Uiso 1 1 calc R U . . .
C13 C 0.1248(3) 1.0229(3) 0.39633(15) 0.0606(10) Uani 1 1 d . . . . .
H13 H 0.127016 1.050708 0.362905 0.073 Uiso 1 1 calc R U . . .
C14 C 0.1142(2) 0.5300(2) 0.54657(11) 0.0332(6) Uani 1 1 d . . . . .
C15 C 0.0970(2) 0.5761(3) 0.59432(11) 0.0394(7) Uani 1 1 d . . . . .
H15 H 0.087702 0.648702 0.596528 0.047 Uiso 1 1 calc R U . . .
C16 C 0.0944(2) 0.5126(3) 0.63722(11) 0.0413(7) Uani 1 1 d . . . . .
H16 H 0.084110 0.541594 0.669159 0.050 Uiso 1 1 calc R U . . .
C17 C 0.1071(2) 0.4040(3) 0.63270(11) 0.0386(7) Uani 1 1 d . . . . .
C18 C 0.1227(2) 0.3635(2) 0.58348(11) 0.0372(7) Uani 1 1 d . . . . .
C19 C 0.1353(3) 0.2546(3) 0.57732(14) 0.0518(8) Uani 1 1 d . . . . .
H19 H 0.145943 0.227818 0.544990 0.062 Uiso 1 1 calc R U . . .
C20 C 0.1319(3) 0.1872(3) 0.61937(16) 0.0631(10) Uani 1 1 d . . . . .
H20 H 0.139305 0.114774 0.615136 0.076 Uiso 1 1 calc R U . . .
C21 C 0.1174(3) 0.2273(3) 0.66843(16) 0.0615(10) Uani 1 1 d . . . . .
H21 H 0.116201 0.181081 0.696582 0.074 Uiso 1 1 calc R U . . .
C22 C 0.1051(3) 0.3323(3) 0.67558(13) 0.0520(9) Uani 1 1 d . . . . .
H22 H 0.095326 0.357572 0.708359 0.062 Uiso 1 1 calc R U . . .
O1A O 0.0468(6) 0.2475(6) 0.3456(8) 0.084(4) Uani 0.56(3) 1 d . . P B 1
H1AA H 0.002382 0.219968 0.357405 0.126 Uiso 0.56(3) 1 d R U P B 1
H1AB H 0.033425 0.267178 0.313771 0.126 Uiso 0.56(3) 1 d R U P B 1
O1B O 0.0666(16) 0.2209(9) 0.3141(6) 0.091(6) Uani 0.44(3) 1 d . . P B 2
H1BA H 0.033541 0.267962 0.293338 0.137 Uiso 0.44(3) 1 d R U P B 2
H1BB H 0.016822 0.216752 0.329972 0.137 Uiso 0.44(3) 1 d R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.962(2) . ?
Cu1 N1 2.047(2) . ?
Cu1 N3 2.047(3) . ?
Cu1 Cl1 2.2184(8) . ?
Cu1 Cl2 2.5077(9) . ?
N1 C1 1.330(4) . ?
N1 C4 1.348(4) . ?
N2 C5 1.339(4) . ?
N2 C9 1.340(3) . ?
N3 C13 1.330(4) . ?
N3 C10 1.349(4) . ?
N4 C2 1.325(4) . ?
N4 C3 1.337(4) . ?
N5 C12 1.317(5) . ?
N5 C11 1.339(5) . ?
N6 C14 1.307(4) . ?
N6 C18 1.381(4) . ?
C1 C2 1.381(5) . ?
C3 C4 1.375(4) . ?
C4 C5 1.483(4) . ?
C5 C6 1.385(4) . ?
C6 C7 1.404(4) . ?
C7 C8 1.392(4) . ?
C7 C14 1.501(4) . ?
C8 C9 1.378(4) . ?
C9 C10 1.474(4) . ?
C10 C11 1.382(4) . ?
C12 C13 1.374(5) . ?
C14 C15 1.412(4) . ?
C15 C16 1.366(4) . ?
C16 C17 1.392(4) . ?
C17 C18 1.412(4) . ?
C17 C22 1.427(4) . ?
C18 C19 1.400(5) . ?
C19 C20 1.380(5) . ?
C20 C21 1.402(5) . ?
C21 C22 1.355(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
N2 Cu1 N1 78.80(9) . . ?
N2 Cu1 N3 78.77(10) . . ?
N1 Cu1 N3 156.73(10) . . ?
N2 Cu1 Cl1 155.90(7) . . ?
N1 Cu1 Cl1 99.46(7) . . ?
N3 Cu1 Cl1 98.46(8) . . ?
N2 Cu1 Cl2 101.70(7) . . ?
N1 Cu1 Cl2 99.88(7) . . ?
N3 Cu1 Cl2 90.66(8) . . ?
Cl1 Cu1 Cl2 102.27(3) . . ?
C1 N1 C4 117.5(3) . . ?
C1 N1 Cu1 127.6(2) . . ?
C4 N1 Cu1 114.82(18) . . ?
C5 N2 C9 121.1(2) . . ?
C5 N2 Cu1 119.75(18) . . ?
C9 N2 Cu1 119.13(19) . . ?
C13 N3 C10 117.7(3) . . ?
C13 N3 Cu1 127.0(2) . . ?
C10 N3 Cu1 114.7(2) . . ?
C2 N4 C3 116.3(3) . . ?
C12 N5 C11 115.9(3) . . ?
C14 N6 C18 117.8(2) . . ?
N1 C1 C2 120.6(3) . . ?
N4 C2 C1 122.7(3) . . ?
N4 C3 C4 122.1(3) . . ?
N1 C4 C3 120.7(3) . . ?
N1 C4 C5 114.7(2) . . ?
C3 C4 C5 124.6(3) . . ?
N2 C5 C6 120.7(2) . . ?
N2 C5 C4 111.9(2) . . ?
C6 C5 C4 127.4(3) . . ?
C5 C6 C7 119.1(3) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 C14 122.0(2) . . ?
C6 C7 C14 119.3(3) . . ?
C9 C8 C7 119.2(3) . . ?
N2 C9 C8 121.1(3) . . ?
N2 C9 C10 112.6(2) . . ?
C8 C9 C10 126.2(3) . . ?
N3 C10 C11 120.1(3) . . ?
N3 C10 C9 114.2(2) . . ?
C11 C10 C9 125.7(3) . . ?
N5 C11 C10 122.3(3) . . ?
N5 C12 C13 123.6(4) . . ?
N3 C13 C12 120.3(3) . . ?
N6 C14 C15 123.6(3) . . ?
N6 C14 C7 116.0(2) . . ?
C15 C14 C7 120.4(3) . . ?
C16 C15 C14 119.0(3) . . ?
C15 C16 C17 119.4(3) . . ?
C16 C17 C18 118.3(3) . . ?
C16 C17 C22 122.8(3) . . ?
C18 C17 C22 118.8(3) . . ?
N6 C18 C19 118.2(3) . . ?
N6 C18 C17 121.8(3) . . ?
C19 C18 C17 120.0(3) . . ?
C20 C19 C18 119.8(3) . . ?
C19 C20 C21 120.3(4) . . ?
C22 C21 C20 121.2(3) . . ?
C21 C22 C17 119.9(3) . . ?

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.061


# start Validation Reply Form
_vrf_PLAT420_cu209               
;
PROBLEM: D-H Without Acceptor       O1A      --H1AB     .     Please Check 
RESPONSE: There is an acceptor of this hydrogen bond donor 
(coordinating Cl ion generated via -x,-1/2+y,1/2-z symmetry transformation)
 which was not counted by CheckCIF software due to geometrical
 limitations implemented for chlorine atoms 
(smaller than chlorine ions, inducing  coordinating ones).
;
# end Validation Reply Form




####################################################################### 
# 
# 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_Cu213a
_database_code_depnum_ccdc_archive 'CCDC 1914395'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Choroba'
;University of Silesia
Poland
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cl2 Cu N6, C H4 O'
_chemical_formula_sum            'C23 H18 Cl2 Cu N6 O'
_chemical_formula_weight         528.87

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'
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'
O O 0.0106 0.0060 '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                   7.8743(3)
_cell_length_b                   10.5456(7)
_cell_length_c                   13.8368(9)
_cell_angle_alpha                97.810(5)
_cell_angle_beta                 96.724(4)
_cell_angle_gamma                93.962(4)
_cell_volume                     1126.28(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3410
_cell_measurement_theta_min      3.9390
_cell_measurement_theta_max      28.2910

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             538
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    1.236
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81347
_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            10462
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.333
_diffrn_reflns_theta_max         25.043
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3993
_reflns_number_gt                3309
_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)+(0.0363P)²+0.2014P] 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         3993
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Cu1 Cu -0.16052(3) 0.65582(3) -0.03957(2) 0.03314(11) Uani 1 1 d . . . . .
Cl1 Cl -0.27834(8) 0.49919(7) -0.15750(6) 0.0505(2) Uani 1 1 d . . . . .
Cl2 Cl -0.39559(7) 0.79336(6) -0.02168(5) 0.04216(18) Uani 1 1 d . . . . .
N1 N -0.0201(2) 0.7556(2) -0.12664(16) 0.0354(5) Uani 1 1 d . . . . .
N2 N 0.0139(2) 0.75727(18) 0.05917(15) 0.0295(4) Uani 1 1 d . . . . .
N3 N -0.1912(2) 0.56909(19) 0.08173(16) 0.0344(5) Uani 1 1 d . . . . .
N4 N 0.1640(3) 0.9246(3) -0.22191(18) 0.0573(7) Uani 1 1 d . . . . .
N5 N -0.2250(3) 0.4851(2) 0.26122(18) 0.0475(6) Uani 1 1 d . . . . .
N6 N 0.6339(3) 1.1370(2) 0.40994(17) 0.0452(6) Uani 1 1 d . . . . .
C1 C -0.0424(3) 0.7481(3) -0.2245(2) 0.0443(7) Uani 1 1 d . . . . .
H1 H -0.1214 0.6857 -0.2620 0.053 Uiso 1 1 calc R U . . .
C2 C 0.0511(3) 0.8322(3) -0.2702(2) 0.0564(8) Uani 1 1 d . . . . .
H2 H 0.0339 0.8237 -0.3385 0.068 Uiso 1 1 calc R U . . .
C3 C 0.1888(3) 0.9299(3) -0.1247(2) 0.0446(7) Uani 1 1 d . . . . .
H3 H 0.2689 0.9923 -0.0881 0.053 Uiso 1 1 calc R U . . .
C4 C 0.0990(3) 0.8454(2) -0.07559(18) 0.0325(6) Uani 1 1 d . . . . .
C5 C 0.1242(3) 0.8438(2) 0.03091(18) 0.0305(5) Uani 1 1 d . . . . .
C6 C 0.2502(3) 0.9155(2) 0.09875(18) 0.0326(6) Uani 1 1 d . . . . .
H6 H 0.3264 0.9750 0.0787 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2615(3) 0.8977(2) 0.19711(18) 0.0308(5) Uani 1 1 d . . . . .
C8 C 0.1444(3) 0.8073(2) 0.22459(18) 0.0327(6) Uani 1 1 d . . . . .
H8 H 0.1482 0.7941 0.2899 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0226(3) 0.7379(2) 0.15275(18) 0.0304(5) Uani 1 1 d . . . . .
C10 C -0.1006(3) 0.6303(2) 0.16579(19) 0.0320(6) Uani 1 1 d . . . . .
C11 C -0.1189(3) 0.5885(3) 0.2543(2) 0.0424(6) Uani 1 1 d . . . . .
H11 H -0.0560 0.6332 0.3113 0.051 Uiso 1 1 calc R U . . .
C12 C -0.3129(3) 0.4270(3) 0.1773(2) 0.0445(7) Uani 1 1 d . . . . .
H12 H -0.3883 0.3557 0.1790 0.053 Uiso 1 1 calc R U . . .
C13 C -0.2980(3) 0.4671(2) 0.0877(2) 0.0393(6) Uani 1 1 d . . . . .
H13 H -0.3626 0.4230 0.0310 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3958(3) 0.9760(2) 0.27029(18) 0.0324(6) Uani 1 1 d . . . . .
C15 C 0.4140(3) 1.1066(2) 0.2714(2) 0.0396(6) Uani 1 1 d . . . . .
H15 H 0.3481 1.1445 0.2249 0.048 Uiso 1 1 calc R U . . .
C16 C 0.5332(3) 1.1827(3) 0.3436(2) 0.0459(7) Uani 1 1 d . . . . .
H16 H 0.5406 1.2711 0.3441 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6270(3) 1.0062(3) 0.40596(19) 0.0380(6) Uani 1 1 d . . . . .
C18 C 0.5084(3) 0.9209(2) 0.33803(18) 0.0333(6) Uani 1 1 d . . . . .
C19 C 0.5154(3) 0.7871(3) 0.3374(2) 0.0428(6) Uani 1 1 d . . . . .
H19 H 0.4401 0.7299 0.2923 0.051 Uiso 1 1 calc R U . . .
C20 C 0.6312(4) 0.7412(3) 0.4020(2) 0.0554(8) Uani 1 1 d . . . . .
H20 H 0.6343 0.6530 0.4012 0.066 Uiso 1 1 calc R U . . .
C21 C 0.7460(4) 0.8267(4) 0.4699(2) 0.0603(9) Uani 1 1 d . . . . .
H21 H 0.8245 0.7944 0.5138 0.072 Uiso 1 1 calc R U . . .
C22 C 0.7446(3) 0.9554(3) 0.4725(2) 0.0520(8) Uani 1 1 d . . . . .
H22 H 0.8213 1.0105 0.5182 0.062 Uiso 1 1 calc R U . . .
O1 O 0.1434(3) 0.6802(2) 0.4566(2) 0.0795(7) Uani 1 1 d . . . . .
H1A H 0.2105 0.7364 0.4905 0.119 Uiso 1 1 calc R U . . .
C23 C 0.2103(5) 0.5613(4) 0.4583(3) 0.0884(12) Uani 1 1 d . . . . .
H23A H 0.1229 0.4940 0.4306 0.133 Uiso 1 1 calc R U . . .
H23B H 0.2491 0.5512 0.5250 0.133 Uiso 1 1 calc R U . . .
H23C H 0.3051 0.5569 0.4205 0.133 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
Cu1 N2 1.9642(19) . ?
Cu1 N3 2.048(2) . ?
Cu1 N1 2.068(2) . ?
Cu1 Cl1 2.2256(7) . ?
Cu1 Cl2 2.4437(7) . ?
N1 C1 1.336(3) . ?
N1 C4 1.347(3) . ?
N2 C9 1.333(3) . ?
N2 C5 1.344(3) . ?
N3 C13 1.336(3) . ?
N3 C10 1.348(3) . ?
N4 C2 1.323(4) . ?
N4 C3 1.329(3) . ?
N5 C12 1.328(4) . ?
N5 C11 1.348(3) . ?
N6 C16 1.306(4) . ?
N6 C17 1.370(3) . ?
C1 C2 1.379(4) . ?
C3 C4 1.396(3) . ?
C4 C5 1.466(3) . ?
C5 C6 1.386(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.401(3) . ?
C7 C14 1.492(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.485(3) . ?
C10 C11 1.376(4) . ?
C12 C13 1.378(4) . ?
C14 C15 1.373(3) . ?
C14 C18 1.424(3) . ?
C15 C16 1.407(4) . ?
C17 C22 1.413(4) . ?
C17 C18 1.419(3) . ?
C18 C19 1.415(4) . ?
C19 C20 1.362(4) . ?
C20 C21 1.404(4) . ?
C21 C22 1.353(4) . ?
O1 C23 1.396(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
N2 Cu1 N3 78.80(8) . . ?
N2 Cu1 N1 78.44(8) . . ?
N3 Cu1 N1 153.97(8) . . ?
N2 Cu1 Cl1 159.36(6) . . ?
N3 Cu1 Cl1 99.85(6) . . ?
N1 Cu1 Cl1 97.01(6) . . ?
N2 Cu1 Cl2 98.42(6) . . ?
N3 Cu1 Cl2 95.57(6) . . ?
N1 Cu1 Cl2 100.09(6) . . ?
Cl1 Cu1 Cl2 102.21(3) . . ?
C1 N1 C4 117.6(2) . . ?
C1 N1 Cu1 128.08(17) . . ?
C4 N1 Cu1 114.07(16) . . ?
C9 N2 C5 121.1(2) . . ?
C9 N2 Cu1 119.49(15) . . ?
C5 N2 Cu1 119.39(16) . . ?
C13 N3 C10 117.7(2) . . ?
C13 N3 Cu1 127.80(18) . . ?
C10 N3 Cu1 114.27(15) . . ?
C2 N4 C3 116.1(2) . . ?
C12 N5 C11 115.7(2) . . ?
C16 N6 C17 117.4(2) . . ?
N1 C1 C2 120.4(2) . . ?
N4 C2 C1 123.3(3) . . ?
N4 C3 C4 122.4(3) . . ?
N1 C4 C3 120.0(2) . . ?
N1 C4 C5 114.9(2) . . ?
C3 C4 C5 125.0(2) . . ?
N2 C5 C6 120.7(2) . . ?
N2 C5 C4 112.5(2) . . ?
C6 C5 C4 126.7(2) . . ?
C5 C6 C7 119.4(2) . . ?
C6 C7 C8 118.7(2) . . ?
C6 C7 C14 119.4(2) . . ?
C8 C7 C14 121.9(2) . . ?
C9 C8 C7 118.9(2) . . ?
N2 C9 C8 121.2(2) . . ?
N2 C9 C10 112.0(2) . . ?
C8 C9 C10 126.6(2) . . ?
N3 C10 C11 120.6(2) . . ?
N3 C10 C9 114.7(2) . . ?
C11 C10 C9 124.7(2) . . ?
N5 C11 C10 122.3(3) . . ?
N5 C12 C13 123.2(2) . . ?
N3 C13 C12 120.4(2) . . ?
C15 C14 C18 118.4(2) . . ?
C15 C14 C7 118.8(2) . . ?
C18 C14 C7 122.9(2) . . ?
C14 C15 C16 119.5(3) . . ?
N6 C16 C15 124.2(3) . . ?
N6 C17 C22 117.9(2) . . ?
N6 C17 C18 122.9(2) . . ?
C22 C17 C18 119.2(3) . . ?
C19 C18 C17 118.7(2) . . ?
C19 C18 C14 123.9(2) . . ?
C17 C18 C14 117.4(2) . . ?
C20 C19 C18 120.6(3) . . ?
C19 C20 C21 120.1(3) . . ?
C22 C21 C20 121.2(3) . . ?
C21 C22 C17 120.2(3) . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.054

_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_Cu199c
_database_code_depnum_ccdc_archive 'CCDC 1914392'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Choroba'
;University of Silesia
Poland
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 Cl2 Cu N4 S2'
_chemical_formula_sum            'C20 H12 Cl2 Cu N4 S2'
_chemical_formula_weight         506.90

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'
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'
S S 0.1246 0.1234 '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                   23.3543(15)
_cell_length_b                   11.0536(6)
_cell_length_c                   7.7194(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1992.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2539
_cell_measurement_theta_min      4.1380
_cell_measurement_theta_max      27.6490

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.589
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75904
_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            8115
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.489
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.816
_reflns_number_total             2947
_reflns_number_gt                2698
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.552
_reflns_Friedel_fraction_max     0.648
_reflns_Friedel_fraction_full    0.631

_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)+(0.0275P)²+0.6538P] 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 916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2947
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Cu1 Cu 0.17106(2) 0.51075(5) 0.19418(9) 0.03428(16) Uani 1 1 d . . . . .
Cl1 Cl 0.11522(6) 0.40628(12) 0.37220(17) 0.0492(4) Uani 1 1 d . . . . .
Cl2 Cl 0.17417(5) 0.71910(11) 0.31872(15) 0.0390(3) Uani 1 1 d . . . . .
S1 S 0.09289(5) 0.63562(11) -0.30240(18) 0.0413(3) Uani 1 1 d . . . . .
S2 S 0.35706(6) 0.44080(11) 0.26938(17) 0.0405(3) Uani 1 1 d . . . . .
N1 N 0.11406(17) 0.5524(3) -0.0020(5) 0.0338(9) Uani 1 1 d . . . . .
N2 N 0.22313(17) 0.5464(3) -0.0021(5) 0.0298(9) Uani 1 1 d . . . . .
N3 N 0.24882(18) 0.4525(3) 0.2909(5) 0.0356(9) Uani 1 1 d . . . . .
N4 N 0.39174(17) 0.6263(3) -0.3667(5) 0.0318(9) Uani 1 1 d . . . . .
C1 C 0.0562(2) 0.5591(4) -0.0151(7) 0.0426(13) Uani 1 1 d . . . . .
H1 H 0.0317 0.5347 0.0731 0.051 Uiso 1 1 calc R U . . .
C2 C 0.0373(2) 0.6044(5) -0.1684(7) 0.0436(13) Uani 1 1 d . . . . .
H2 H -0.0010 0.6167 -0.1961 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1394(2) 0.5895(4) -0.1457(6) 0.0298(10) Uani 1 1 d . . . . .
C4 C 0.2021(2) 0.5897(4) -0.1503(5) 0.0277(10) Uani 1 1 d . . . . .
C5 C 0.23773(19) 0.6286(3) -0.2818(6) 0.0289(10) Uani 1 1 d . . . . .
H5 H 0.2225 0.6585 -0.3846 0.035 Uiso 1 1 calc R U . . .
C6 C 0.29698(19) 0.6222(4) -0.2582(5) 0.0285(10) Uani 1 1 d . . . . .
C7 C 0.3181(2) 0.5761(4) -0.1018(6) 0.0333(11) Uani 1 1 d . . . . .
H7 H 0.3573 0.5721 -0.0811 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2793(2) 0.5366(4) 0.0211(6) 0.0304(11) Uani 1 1 d . . . . .
C9 C 0.29204(18) 0.4803(4) 0.1888(7) 0.0312(9) Uani 1 1 d . . . . .
C10 C 0.3243(3) 0.3852(4) 0.4504(6) 0.0413(13) Uani 1 1 d . . . . .
H10 H 0.3434 0.3502 0.5436 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2679(2) 0.3986(4) 0.4401(6) 0.0383(12) Uani 1 1 d . . . . .
H11 H 0.2432 0.3734 0.5275 0.046 Uiso 1 1 calc R U . . .
C12 C 0.3387(2) 0.6630(4) -0.3917(6) 0.0293(11) Uani 1 1 d . . . . .
C13 C 0.3215(2) 0.7326(4) -0.5361(6) 0.0349(11) Uani 1 1 d . . . . .
H13 H 0.2836 0.7563 -0.5493 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3616(2) 0.7641(4) -0.6553(7) 0.0374(12) Uani 1 1 d . . . . .
H14 H 0.3512 0.8105 -0.7507 0.045 Uiso 1 1 calc R U . . .
C15 C 0.4188(2) 0.7267(4) -0.6349(6) 0.0346(11) Uani 1 1 d . . . . .
C16 C 0.4320(2) 0.6575(4) -0.4864(6) 0.0333(11) Uani 1 1 d . . . . .
C17 C 0.4890(2) 0.6173(5) -0.4609(7) 0.0448(13) Uani 1 1 d . . . . .
H17 H 0.4982 0.5720 -0.3634 0.054 Uiso 1 1 calc R U . . .
C18 C 0.5305(3) 0.6452(5) -0.5793(7) 0.0529(15) Uani 1 1 d . . . . .
H18 H 0.5679 0.6193 -0.5613 0.063 Uiso 1 1 calc R U . . .
C19 C 0.5170(2) 0.7119(5) -0.7268(7) 0.0557(16) Uani 1 1 d . . . . .
H19 H 0.5457 0.7293 -0.8067 0.067 Uiso 1 1 calc R U . . .
C20 C 0.4629(2) 0.7522(5) -0.7564(7) 0.0505(14) Uani 1 1 d . . . . .
H20 H 0.4547 0.7964 -0.8559 0.061 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
Cu1 N2 1.983(4) . ?
Cu1 N3 2.067(4) . ?
Cu1 N1 2.068(4) . ?
Cu1 Cl1 2.2187(14) . ?
Cu1 Cl2 2.4966(13) . ?
S1 C2 1.695(5) . ?
S1 C3 1.703(5) . ?
S2 C9 1.698(5) . ?
S2 C10 1.707(5) . ?
N1 C3 1.322(6) . ?
N1 C1 1.356(6) . ?
N2 C8 1.329(6) . ?
N2 C4 1.333(6) . ?
N3 C9 1.317(6) . ?
N3 C11 1.371(6) . ?
N4 C12 1.318(6) . ?
N4 C16 1.363(6) . ?
C1 C2 1.359(8) . ?
C3 C4 1.467(6) . ?
C4 C5 1.381(6) . ?
C5 C6 1.397(6) . ?
C6 C7 1.401(6) . ?
C6 C12 1.488(6) . ?
C7 C8 1.383(7) . ?
C8 C9 1.466(7) . ?
C10 C11 1.328(7) . ?
C12 C13 1.413(6) . ?
C13 C14 1.357(7) . ?
C14 C15 1.408(6) . ?
C15 C16 1.412(7) . ?
C15 C20 1.421(7) . ?
C16 C17 1.417(7) . ?
C17 C18 1.367(7) . ?
C18 C19 1.392(7) . ?
C19 C20 1.360(7) . ?

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
N2 Cu1 N3 78.41(16) . . ?
N2 Cu1 N1 77.93(16) . . ?
N3 Cu1 N1 154.11(16) . . ?
N2 Cu1 Cl1 159.62(11) . . ?
N3 Cu1 Cl1 97.50(11) . . ?
N1 Cu1 Cl1 101.01(11) . . ?
N2 Cu1 Cl2 95.35(11) . . ?
N3 Cu1 Cl2 97.05(11) . . ?
N1 Cu1 Cl2 95.48(11) . . ?
Cl1 Cu1 Cl2 105.00(5) . . ?
C2 S1 C3 89.6(3) . . ?
C9 S2 C10 89.6(3) . . ?
C3 N1 C1 111.4(4) . . ?
C3 N1 Cu1 113.3(3) . . ?
C1 N1 Cu1 135.0(3) . . ?
C8 N2 C4 120.5(4) . . ?
C8 N2 Cu1 119.1(3) . . ?
C4 N2 Cu1 120.1(3) . . ?
C9 N3 C11 110.8(4) . . ?
C9 N3 Cu1 112.6(3) . . ?
C11 N3 Cu1 136.5(3) . . ?
C12 N4 C16 118.2(4) . . ?
N1 C1 C2 114.1(5) . . ?
C1 C2 S1 111.0(4) . . ?
N1 C3 C4 117.9(4) . . ?
N1 C3 S1 113.8(4) . . ?
C4 C3 S1 128.3(3) . . ?
N2 C4 C5 121.4(4) . . ?
N2 C4 C3 110.3(4) . . ?
C5 C4 C3 128.3(4) . . ?
C4 C5 C6 119.0(4) . . ?
C5 C6 C7 118.7(4) . . ?
C5 C6 C12 122.9(4) . . ?
C7 C6 C12 118.4(4) . . ?
C8 C7 C6 118.4(4) . . ?
N2 C8 C7 121.9(4) . . ?
N2 C8 C9 110.7(4) . . ?
C7 C8 C9 127.4(4) . . ?
N3 C9 C8 118.2(4) . . ?
N3 C9 S2 113.9(4) . . ?
C8 C9 S2 127.8(4) . . ?
C11 C10 S2 110.8(4) . . ?
C10 C11 N3 114.9(5) . . ?
N4 C12 C13 123.3(4) . . ?
N4 C12 C6 114.9(4) . . ?
C13 C12 C6 121.7(4) . . ?
C14 C13 C12 118.6(5) . . ?
C13 C14 C15 120.2(5) . . ?
C14 C15 C16 117.2(4) . . ?
C14 C15 C20 123.8(5) . . ?
C16 C15 C20 119.0(4) . . ?
N4 C16 C15 122.5(4) . . ?
N4 C16 C17 118.3(4) . . ?
C15 C16 C17 119.2(4) . . ?
C18 C17 C16 120.1(5) . . ?
C17 C18 C19 120.4(5) . . ?
C20 C19 C18 121.3(5) . . ?
C19 C20 C15 119.9(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 Cl1 0.93 2.73 3.578(5) 151.9 2_564
C5 H5 Cl2 0.93 2.64 3.565(5) 173.5 1_554
C10 H10 Cl2 0.93 2.60 3.384(5) 141.8 3_545
C13 H13 Cl2 0.93 2.78 3.622(5) 150.9 1_554

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055

_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_Cu208
_database_code_depnum_ccdc_archive 'CCDC 1914391'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Choroba'
;University of Silesia
Poland
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 Cl2 Cu N4'
_chemical_formula_sum            'C24 H16 Cl2 Cu N4'
_chemical_formula_weight         494.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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/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                   7.9474(5)
_cell_length_b                   22.7151(11)
_cell_length_c                   11.6628(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.888(6)
_cell_angle_gamma                90
_cell_volume                     2102.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2802
_cell_measurement_theta_min      3.9730
_cell_measurement_theta_max      25.8970

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             1004
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.313
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60861
_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            8451
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.302
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3711
_reflns_number_gt                2426
_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)+(0.0387P)²+1.8606P] 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         3711
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
Cu1 Cu 0.35032(9) 0.17357(3) 0.57651(6) 0.0395(2) Uani 1 1 d . . . . .
Cl1 Cl 0.2170(2) 0.08722(6) 0.56968(14) 0.0600(5) Uani 1 1 d . . . . .
Cl2 Cl 0.49999(17) 0.18594(6) 0.76920(11) 0.0426(4) Uani 1 1 d . . . . .
N1 N 0.1555(5) 0.22709(19) 0.6210(4) 0.0385(11) Uani 1 1 d . . . . .
N2 N 0.4307(5) 0.25015(17) 0.5279(3) 0.0329(10) Uani 1 1 d . . . . .
N3 N 0.5564(6) 0.14925(19) 0.4886(4) 0.0410(11) Uani 1 1 d . . . . .
N4 N 0.8124(6) 0.5257(2) 0.4349(4) 0.0481(13) Uani 1 1 d . . . . .
C1 C 0.0143(7) 0.2116(3) 0.6693(5) 0.0498(15) Uani 1 1 d . . . . .
H1 H -0.0076 0.1716 0.6778 0.060 Uiso 1 1 calc R U . . .
C2 C -0.0999(7) 0.2506(3) 0.7069(5) 0.0520(16) Uani 1 1 d . . . . .
H2 H -0.1968 0.2375 0.7405 0.062 Uiso 1 1 calc R U . . .
C3 C -0.0696(7) 0.3098(3) 0.6943(5) 0.0511(16) Uani 1 1 d . . . . .
H3 H -0.1455 0.3375 0.7200 0.061 Uiso 1 1 calc R U . . .
C4 C 0.0754(7) 0.3278(3) 0.6430(5) 0.0450(14) Uani 1 1 d . . . . .
H4 H 0.0971 0.3676 0.6318 0.054 Uiso 1 1 calc R U . . .
C5 C 0.1871(6) 0.2852(2) 0.6089(4) 0.0347(12) Uani 1 1 d . . . . .
C6 C 0.3504(6) 0.2982(2) 0.5595(4) 0.0339(12) Uani 1 1 d . . . . .
C7 C 0.4193(6) 0.3532(2) 0.5468(4) 0.0373(13) Uani 1 1 d . . . . .
H7 H 0.3625 0.3865 0.5704 0.045 Uiso 1 1 calc R U . . .
C8 C 0.5767(7) 0.3585(2) 0.4976(4) 0.0351(12) Uani 1 1 d . . . . .
C9 C 0.6564(7) 0.3071(2) 0.4640(4) 0.0355(12) Uani 1 1 d . . . . .
H9 H 0.7596 0.3090 0.4300 0.043 Uiso 1 1 calc R U . . .
C10 C 0.5816(7) 0.2536(2) 0.4815(4) 0.0298(12) Uani 1 1 d . . . . .
C11 C 0.6533(7) 0.1954(2) 0.4590(4) 0.0328(12) Uani 1 1 d . . . . .
C12 C 0.8057(7) 0.1863(2) 0.4105(4) 0.0452(15) Uani 1 1 d . . . . .
H12 H 0.8696 0.2182 0.3882 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8629(9) 0.1298(3) 0.3954(5) 0.0554(17) Uani 1 1 d . . . . .
H13 H 0.9676 0.1233 0.3655 0.066 Uiso 1 1 calc R U . . .
C14 C 0.7646(9) 0.0833(3) 0.4246(5) 0.0607(18) Uani 1 1 d . . . . .
H14 H 0.7995 0.0448 0.4125 0.073 Uiso 1 1 calc R U . . .
C15 C 0.6119(9) 0.0946(2) 0.4725(5) 0.0510(16) Uani 1 1 d . . . . .
H15 H 0.5459 0.0631 0.4942 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6595(7) 0.4163(2) 0.4815(4) 0.0367(13) Uani 1 1 d . . . . .
C17 C 0.6870(7) 0.4586(2) 0.5715(4) 0.0383(13) Uani 1 1 d . . . . .
C18 C 0.6463(8) 0.4500(3) 0.6873(5) 0.0506(15) Uani 1 1 d . . . . .
H18 H 0.5951 0.4150 0.7080 0.061 Uiso 1 1 calc R U . . .
C19 C 0.6799(9) 0.4909(3) 0.7670(6) 0.069(2) Uani 1 1 d . . . . .
H19 H 0.6520 0.4842 0.8424 0.083 Uiso 1 1 calc R U . . .
C20 C 0.7566(9) 0.5439(3) 0.7383(6) 0.0633(19) Uani 1 1 d . . . . .
H20 H 0.7806 0.5719 0.7948 0.076 Uiso 1 1 calc R U . . .
C21 C 0.7959(8) 0.5545(3) 0.6299(6) 0.0540(16) Uani 1 1 d . . . . .
H21 H 0.8442 0.5904 0.6117 0.065 Uiso 1 1 calc R U . . .
C22 C 0.7654(7) 0.5125(2) 0.5440(5) 0.0385(13) Uani 1 1 d . . . . .
C23 C 0.7871(7) 0.4854(2) 0.3579(5) 0.0439(14) Uani 1 1 d . . . . .
H23 H 0.8194 0.4936 0.2840 0.053 Uiso 1 1 calc R U . . .
C24 C 0.7149(7) 0.4305(2) 0.3771(5) 0.0440(14) Uani 1 1 d . . . . .
H24 H 0.7046 0.4033 0.3176 0.053 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
Cu1 N2 1.947(4) . ?
Cu1 N3 2.052(5) . ?
Cu1 N1 2.055(4) . ?
Cu1 Cl1 2.2289(15) . ?
Cu1 Cl2 2.5050(15) . ?
N1 C1 1.329(7) . ?
N1 C5 1.353(6) . ?
N2 C6 1.326(6) . ?
N2 C10 1.343(6) . ?
N3 C15 1.334(7) . ?
N3 C11 1.355(6) . ?
N4 C23 1.291(7) . ?
N4 C22 1.377(7) . ?
C1 C2 1.357(8) . ?
C2 C3 1.377(8) . ?
C3 C4 1.387(8) . ?
C4 C5 1.385(7) . ?
C5 C6 1.476(7) . ?
C6 C7 1.374(7) . ?
C7 C8 1.407(7) . ?
C8 C9 1.395(7) . ?
C8 C16 1.485(7) . ?
C9 C10 1.373(7) . ?
C10 C11 1.468(7) . ?
C11 C12 1.378(7) . ?
C12 C13 1.377(8) . ?
C13 C14 1.367(9) . ?
C14 C15 1.385(8) . ?
C16 C24 1.353(7) . ?
C16 C17 1.431(7) . ?
C17 C22 1.419(7) . ?
C17 C18 1.418(7) . ?
C18 C19 1.332(8) . ?
C19 C20 1.397(9) . ?
C20 C21 1.339(8) . ?
C21 C22 1.396(8) . ?
C23 C24 1.396(7) . ?

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
N2 Cu1 N3 79.23(18) . . ?
N2 Cu1 N1 78.89(18) . . ?
N3 Cu1 N1 156.33(17) . . ?
N2 Cu1 Cl1 159.71(13) . . ?
N3 Cu1 Cl1 97.78(13) . . ?
N1 Cu1 Cl1 99.60(13) . . ?
N2 Cu1 Cl2 90.76(12) . . ?
N3 Cu1 Cl2 97.10(13) . . ?
N1 Cu1 Cl2 92.11(12) . . ?
Cl1 Cu1 Cl2 109.53(6) . . ?
C1 N1 C5 117.9(5) . . ?
C1 N1 Cu1 127.8(4) . . ?
C5 N1 Cu1 113.9(3) . . ?
C6 N2 C10 121.1(4) . . ?
C6 N2 Cu1 119.0(4) . . ?
C10 N2 Cu1 118.8(3) . . ?
C15 N3 C11 119.2(5) . . ?
C15 N3 Cu1 126.8(4) . . ?
C11 N3 Cu1 113.4(3) . . ?
C23 N4 C22 116.7(5) . . ?
N1 C1 C2 123.8(6) . . ?
C1 C2 C3 118.7(6) . . ?
C2 C3 C4 119.2(6) . . ?
C5 C4 C3 118.5(5) . . ?
N1 C5 C4 121.8(5) . . ?
N1 C5 C6 114.0(4) . . ?
C4 C5 C6 124.2(5) . . ?
N2 C6 C7 121.2(5) . . ?
N2 C6 C5 112.9(4) . . ?
C7 C6 C5 125.9(5) . . ?
C6 C7 C8 119.3(5) . . ?
C9 C8 C7 117.9(5) . . ?
C9 C8 C16 119.6(5) . . ?
C7 C8 C16 122.5(5) . . ?
C10 C9 C8 119.6(5) . . ?
N2 C10 C9 120.9(4) . . ?
N2 C10 C11 112.5(4) . . ?
C9 C10 C11 126.6(5) . . ?
N3 C11 C12 120.7(5) . . ?
N3 C11 C10 114.9(5) . . ?
C12 C11 C10 124.4(5) . . ?
C13 C12 C11 119.7(6) . . ?
C14 C13 C12 119.4(6) . . ?
C13 C14 C15 118.7(6) . . ?
N3 C15 C14 122.1(6) . . ?
C24 C16 C17 117.1(5) . . ?
C24 C16 C8 119.4(5) . . ?
C17 C16 C8 123.5(5) . . ?
C22 C17 C18 117.3(5) . . ?
C22 C17 C16 117.8(5) . . ?
C18 C17 C16 124.9(5) . . ?
C19 C18 C17 121.4(6) . . ?
C18 C19 C20 120.5(6) . . ?
C21 C20 C19 120.5(6) . . ?
C20 C21 C22 120.9(6) . . ?
N4 C22 C21 118.0(5) . . ?
N4 C22 C17 122.6(5) . . ?
C21 C22 C17 119.4(5) . . ?
N4 C23 C24 124.9(5) . . ?
C16 C24 C23 120.8(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 2.72 3.609(6) 161.5 1_455
C7 H7 N4 0.93 2.43 3.324(7) 161.0 3_666
C9 H9 Cl2 0.93 2.75 3.643(6) 162.2 4_665
C12 H12 Cl2 0.93 2.81 3.712(6) 164.5 4_665
C21 H21 Cl2 0.93 2.83 3.568(6) 137.3 2_656

_refine_diff_density_max         0.595
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.082

_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_Cu207a
_database_code_depnum_ccdc_archive 'CCDC 1914393'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Choroba'
;University of Silesia
Poland
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_Cu207a              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: Number of collected reflections is 8252 (independent - 3779),
 which is enough for a satisfactory refinement.
All of the missing reflections are below theta = 3.4 deg.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 Cl2 Cu N4 S2, 3(H2 O)'
_chemical_formula_sum            'C20 H18 Cl2 Cu N4 O3 S2'
_chemical_formula_weight         560.94

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'
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'
S S 0.1246 0.1234 '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'

_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                   7.8923(5)
_cell_length_b                   11.31080(10)
_cell_length_c                   13.6000(14)
_cell_angle_alpha                71.716(9)
_cell_angle_beta                 74.885(7)
_cell_angle_gamma                87.322(6)
_cell_volume                     1112.06(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3995
_cell_measurement_theta_min      3.5870
_cell_measurement_theta_max      28.9990

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             570
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    1.442
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76370
_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            8252
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.478
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             3779
_reflns_number_gt                2714
_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)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3779
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Cu1 Cu 0.75440(6) 0.18715(5) 0.11589(4) 0.0318(2) Uani 1 1 d . . . . .
Cl1 Cl 0.60858(17) 0.04651(12) 0.26709(12) 0.0553(4) Uani 1 1 d . . . . .
Cl2 Cl 0.84318(15) 0.35868(11) 0.16587(11) 0.0437(4) Uani 1 1 d . . . . .
S1 S 0.42592(14) 0.42022(11) -0.08469(11) 0.0366(3) Uani 1 1 d . . . . .
S2 S 1.29267(14) 0.06907(11) -0.00854(10) 0.0371(3) Uani 1 1 d . . . . .
N1 N 0.5465(4) 0.2726(3) 0.0622(3) 0.0310(9) Uani 1 1 d . . . . .
N2 N 0.8620(4) 0.2516(3) -0.0400(3) 0.0296(9) Uani 1 1 d . . . . .
N3 N 0.9919(4) 0.1028(3) 0.1014(3) 0.0309(9) Uani 1 1 d . . . . .
N4 N 1.2964(5) 0.5951(4) -0.5683(3) 0.0406(10) Uani 1 1 d . . . . .
C1 C 0.3757(6) 0.2911(4) 0.1099(4) 0.0375(12) Uani 1 1 d . . . . .
H1 H 0.3229 0.2534 0.1823 0.045 Uiso 1 1 calc R U . . .
C2 C 0.2911(6) 0.3690(4) 0.0422(4) 0.0376(12) Uani 1 1 d . . . . .
H2 H 0.1754 0.3917 0.0620 0.045 Uiso 1 1 calc R U . . .
C3 C 0.5894(5) 0.3351(4) -0.0399(4) 0.0308(11) Uani 1 1 d . . . . .
C4 C 0.7701(5) 0.3289(4) -0.1024(4) 0.0296(11) Uani 1 1 d . . . . .
C5 C 0.8462(5) 0.3878(4) -0.2088(4) 0.0306(11) Uani 1 1 d . . . . .
H5 H 0.7811 0.4405 -0.2515 0.037 Uiso 1 1 calc R U . . .
C6 C 1.0238(5) 0.3681(4) -0.2534(4) 0.0338(11) Uani 1 1 d . . . . .
C7 C 1.1144(5) 0.2852(4) -0.1874(4) 0.0325(11) Uani 1 1 d . . . . .
H7 H 1.2305 0.2680 -0.2142 0.039 Uiso 1 1 calc R U . . .
C8 C 1.0279(5) 0.2289(4) -0.0810(4) 0.0273(10) Uani 1 1 d . . . . .
C9 C 1.0953(5) 0.1387(4) 0.0035(4) 0.0275(10) Uani 1 1 d . . . . .
C10 C 1.2322(6) -0.0107(4) 0.1244(4) 0.0422(13) Uani 1 1 d . . . . .
H10 H 1.3019 -0.0673 0.1605 0.051 Uiso 1 1 calc R U . . .
C11 C 1.0707(6) 0.0186(4) 0.1708(4) 0.0373(12) Uani 1 1 d . . . . .
H11 H 1.0172 -0.0154 0.2436 0.045 Uiso 1 1 calc R U . . .
C12 C 1.1117(5) 0.4410(4) -0.3641(4) 0.0329(11) Uani 1 1 d . . . . .
C13 C 1.0910(6) 0.5675(4) -0.3979(4) 0.0415(13) Uani 1 1 d . . . . .
H13 H 1.0150 0.6050 -0.3528 0.050 Uiso 1 1 calc R U . . .
C14 C 1.1841(7) 0.6393(5) -0.4997(4) 0.0459(14) Uani 1 1 d . . . . .
H14 H 1.1655 0.7243 -0.5206 0.055 Uiso 1 1 calc R U . . .
C15 C 1.3174(6) 0.4697(4) -0.5385(4) 0.0370(12) Uani 1 1 d . . . . .
C16 C 1.2251(6) 0.3872(4) -0.4384(4) 0.0363(12) Uani 1 1 d . . . . .
C17 C 1.2461(7) 0.2572(5) -0.4190(5) 0.0477(14) Uani 1 1 d . . . . .
H17 H 1.1846 0.2011 -0.3545 0.057 Uiso 1 1 calc R U . . .
C18 C 1.3577(8) 0.2143(5) -0.4957(5) 0.0585(16) Uani 1 1 d . . . . .
H18 H 1.3691 0.1290 -0.4831 0.070 Uiso 1 1 calc R U . . .
C19 C 1.4524(8) 0.2962(6) -0.5907(5) 0.0622(18) Uani 1 1 d . . . . .
H19 H 1.5296 0.2652 -0.6404 0.075 Uiso 1 1 calc R U . . .
C20 C 1.4358(7) 0.4197(6) -0.6131(5) 0.0535(16) Uani 1 1 d . . . . .
H20 H 1.5018 0.4731 -0.6776 0.064 Uiso 1 1 calc R U . . .
O1 O 1.4736(5) -0.2145(3) 0.2470(3) 0.0494(10) Uani 1 1 d G . . . .
H1A H 1.4119 -0.2691 0.3017 0.074 Uiso 1 1 d G U . . .
H1B H 1.5057 -0.1562 0.2660 0.074 Uiso 1 1 d G U . . .
O2 O 1.2071(7) 0.9657(5) -0.5890(6) 0.116(2) Uani 1 1 d G . . . .
H2A H 1.3082 1.0016 -0.6175 0.173 Uiso 1 1 d G U . . .
H2B H 1.1371 1.0250 -0.5879 0.173 Uiso 1 1 d G U . . .
O3 O 0.9617(8) 1.1440(7) -0.6303(6) 0.123(2) Uani 1 1 d G . . . .
H3A H 0.9132 1.1978 -0.6728 0.184 Uiso 1 1 d G U . . .
H3B H 0.8774 1.1092 -0.5766 0.184 Uiso 1 1 d G 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
Cu1 N2 1.973(4) . ?
Cu1 N1 2.048(3) . ?
Cu1 N3 2.055(3) . ?
Cu1 Cl1 2.2289(13) . ?
Cu1 Cl2 2.4332(15) . ?
S1 C3 1.700(4) . ?
S1 C2 1.709(5) . ?
S2 C10 1.696(5) . ?
S2 C9 1.705(4) . ?
N1 C3 1.305(6) . ?
N1 C1 1.373(6) . ?
N2 C8 1.330(5) . ?
N2 C4 1.344(5) . ?
N3 C9 1.315(6) . ?
N3 C11 1.368(5) . ?
N4 C14 1.313(7) . ?
N4 C15 1.363(6) . ?
C1 C2 1.351(6) . ?
C3 C4 1.468(6) . ?
C4 C5 1.371(6) . ?
C5 C6 1.412(6) . ?
C6 C7 1.393(6) . ?
C6 C12 1.469(6) . ?
C7 C8 1.382(6) . ?
C8 C9 1.475(6) . ?
C10 C11 1.343(7) . ?
C12 C13 1.375(6) . ?
C12 C16 1.433(7) . ?
C13 C14 1.391(7) . ?
C15 C16 1.415(6) . ?
C15 C20 1.428(8) . ?
C16 C17 1.420(7) . ?
C17 C18 1.378(8) . ?
C18 C19 1.377(8) . ?
C19 C20 1.341(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
N2 Cu1 N1 78.92(14) . . ?
N2 Cu1 N3 77.90(14) . . ?
N1 Cu1 N3 154.91(17) . . ?
N2 Cu1 Cl1 154.73(12) . . ?
N1 Cu1 Cl1 99.50(11) . . ?
N3 Cu1 Cl1 97.35(10) . . ?
N2 Cu1 Cl2 98.42(12) . . ?
N1 Cu1 Cl2 96.35(11) . . ?
N3 Cu1 Cl2 96.42(11) . . ?
Cl1 Cu1 Cl2 106.80(6) . . ?
C3 S1 C2 89.4(2) . . ?
C10 S2 C9 89.5(2) . . ?
C3 N1 C1 111.3(4) . . ?
C3 N1 Cu1 113.1(3) . . ?
C1 N1 Cu1 135.1(3) . . ?
C8 N2 C4 120.5(4) . . ?
C8 N2 Cu1 120.7(3) . . ?
C4 N2 Cu1 118.5(3) . . ?
C9 N3 C11 111.5(4) . . ?
C9 N3 Cu1 113.6(3) . . ?
C11 N3 Cu1 134.9(3) . . ?
C14 N4 C15 117.2(4) . . ?
C2 C1 N1 114.0(4) . . ?
C1 C2 S1 110.6(3) . . ?
N1 C3 C4 118.3(3) . . ?
N1 C3 S1 114.5(3) . . ?
C4 C3 S1 127.1(3) . . ?
N2 C4 C5 120.8(4) . . ?
N2 C4 C3 110.3(4) . . ?
C5 C4 C3 128.9(4) . . ?
C4 C5 C6 119.7(4) . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 C12 121.7(4) . . ?
C5 C6 C12 120.0(4) . . ?
C8 C7 C6 118.6(4) . . ?
N2 C8 C7 122.2(4) . . ?
N2 C8 C9 109.3(4) . . ?
C7 C8 C9 128.5(4) . . ?
N3 C9 C8 117.9(4) . . ?
N3 C9 S2 113.7(3) . . ?
C8 C9 S2 128.4(3) . . ?
C11 C10 S2 111.3(3) . . ?
C10 C11 N3 114.0(4) . . ?
C13 C12 C16 117.8(4) . . ?
C13 C12 C6 119.2(5) . . ?
C16 C12 C6 123.0(4) . . ?
C12 C13 C14 119.9(5) . . ?
N4 C14 C13 124.5(5) . . ?
N4 C15 C16 123.1(5) . . ?
N4 C15 C20 118.0(4) . . ?
C16 C15 C20 118.9(5) . . ?
C15 C16 C17 118.4(5) . . ?
C15 C16 C12 117.4(4) . . ?
C17 C16 C12 124.2(4) . . ?
C18 C17 C16 120.0(5) . . ?
C19 C18 C17 120.8(5) . . ?
C20 C19 C18 121.4(6) . . ?
C19 C20 C15 120.4(5) . . ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.117

_shelxl_version_number           2014/6

