# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_apohost
_database_code_depnum_ccdc_archive 'CCDC 1566860'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            1_apohost
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8'
_chemical_formula_sum            'C34 H40 Cl4 Cu2 N8'
_chemical_formula_weight         829.62

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/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                   8.327(2)
_cell_length_b                   10.489(3)
_cell_length_c                   22.225(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.546(3)
_cell_angle_gamma                90
_cell_volume                     1919.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1381
_cell_measurement_theta_min      2.698
_cell_measurement_theta_max      25.2095

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.175
_exptl_absorpt_coefficient_mu    1.422
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.789
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_T_max  0.7890
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10547
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         28.241
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4412
_reflns_number_gt                2788
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4412
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.928
_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 0.02295(5) 0.72357(4) 0.40190(2) 0.01757(13) Uani 1 1 d . . . . .
Cl1 Cl 0.16076(11) 0.68523(9) 0.32344(4) 0.0242(2) Uani 1 1 d . . . . .
Cl2 Cl -0.12225(11) 0.85838(10) 0.45279(4) 0.0299(2) Uani 1 1 d . . . . .
N4 N 0.1715(4) 0.3691(3) 0.63693(13) 0.0193(7) Uani 1 1 d . . . . .
N1 N 0.2248(4) 0.7537(3) 0.45933(12) 0.0202(7) Uani 1 1 d . . . . .
N3 N 0.3320(3) 0.4985(3) 0.69574(12) 0.0176(6) Uani 1 1 d . . . . .
C5 C 0.5418(4) 0.8459(3) 0.63643(14) 0.0144(7) Uani 1 1 d . . . . .
C8 C 0.7704(4) 0.7646(3) 0.70416(14) 0.0173(8) Uani 1 1 d . . . . .
H8 H 0.883836 0.764078 0.718304 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4745(4) 0.9238(3) 0.58060(15) 0.0203(8) Uani 1 1 d . . . . .
H4A H 0.390104 0.982955 0.590968 0.024 Uiso 1 1 calc R U . . .
H4B H 0.562617 0.975137 0.567362 0.024 Uiso 1 1 calc R U . . .
C13 C 0.2555(4) 0.7759(4) 0.64580(15) 0.0216(8) Uani 1 1 d . . . . .
H13A H 0.225828 0.858334 0.626567 0.032 Uiso 1 1 calc R U . . .
H13B H 0.199641 0.765153 0.681295 0.032 Uiso 1 1 calc R U . . .
H13C H 0.223371 0.707209 0.616587 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4373(4) 0.7712(3) 0.66581(14) 0.0153(7) Uani 1 1 d . . . . .
N2 N 0.4036(3) 0.8391(3) 0.53059(12) 0.0185(7) Uani 1 1 d . . . . .
C3 C 0.2506(4) 0.8459(3) 0.50023(15) 0.0184(8) Uani 1 1 d . . . . .
H3 H 0.172610 0.908104 0.507291 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5021(4) 0.6886(3) 0.71320(14) 0.0148(7) Uani 1 1 d . . . . .
C9 C 0.6710(4) 0.6841(3) 0.73183(14) 0.0161(8) Uani 1 1 d . . . . .
C2 C 0.4771(5) 0.7359(4) 0.50827(16) 0.0264(9) Uani 1 1 d . . . . .
H2 H 0.584626 0.706507 0.521074 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7110(4) 0.8459(3) 0.65661(15) 0.0165(8) Uani 1 1 d . . . . .
C10 C 0.7486(5) 0.5915(4) 0.77999(16) 0.0252(9) Uani 1 1 d . . . . .
H10A H 0.866351 0.604952 0.787166 0.038 Uiso 1 1 calc R U . . .
H10B H 0.725280 0.503862 0.766018 0.038 Uiso 1 1 calc R U . . .
H10C H 0.704306 0.605717 0.817895 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3913(4) 0.5981(3) 0.74008(15) 0.0197(8) Uani 1 1 d . . . . .
H14A H 0.450903 0.558243 0.777213 0.024 Uiso 1 1 calc R U . . .
H14B H 0.297995 0.645742 0.751715 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1790(4) 0.4590(3) 0.67920(14) 0.0170(8) Uani 1 1 d . . . . .
H17 H 0.087924 0.491015 0.695572 0.020 Uiso 1 1 calc R U . . .
C7 C 0.8280(4) 0.9307(4) 0.62894(16) 0.0253(9) Uani 1 1 d . . . . .
H7A H 0.937833 0.919637 0.651262 0.038 Uiso 1 1 calc R U . . .
H7B H 0.794888 1.019914 0.631466 0.038 Uiso 1 1 calc R U . . .
H7C H 0.827128 0.907235 0.586205 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4290(5) 0.4290(4) 0.66306(17) 0.0243(9) Uani 1 1 d . . . . .
H15 H 0.543619 0.435210 0.665381 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3293(5) 0.3504(4) 0.62708(16) 0.0244(9) Uani 1 1 d . . . . .
H16 H 0.362591 0.291042 0.599118 0.029 Uiso 1 1 calc R U . . .
C1 C 0.3656(5) 0.6841(4) 0.46428(17) 0.0289(10) Uani 1 1 d . . . . .
H1 H 0.382518 0.611205 0.440649 0.035 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 N4 1.974(3) 3_566 ?
Cu1 N1 1.979(3) . ?
Cu1 Cl1 2.2614(10) . ?
Cu1 Cl2 2.2687(11) . ?
N4 C17 1.325(4) . ?
N4 C16 1.378(5) . ?
N1 C3 1.323(4) . ?
N1 C1 1.372(5) . ?
N3 C17 1.338(4) . ?
N3 C15 1.373(4) . ?
N3 C14 1.470(4) . ?
C5 C12 1.402(5) . ?
C5 C6 1.414(5) . ?
C5 C4 1.521(4) . ?
C8 C9 1.389(5) . ?
C8 C6 1.391(5) . ?
C8 H8 0.9500 . ?
C4 N2 1.475(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C13 C12 1.514(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 C11 1.408(5) . ?
N2 C3 1.352(4) . ?
N2 C2 1.372(5) . ?
C3 H3 0.9500 . ?
C11 C9 1.406(5) . ?
C11 C14 1.508(5) . ?
C9 C10 1.517(5) . ?
C2 C1 1.357(5) . ?
C2 H2 0.9500 . ?
C6 C7 1.516(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 H17 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 C16 1.346(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C1 H1 0.9500 . ?

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
N4 Cu1 N1 157.44(12) 3_566 . ?
N4 Cu1 Cl1 93.01(9) 3_566 . ?
N1 Cu1 Cl1 92.65(9) . . ?
N4 Cu1 Cl2 93.54(9) 3_566 . ?
N1 Cu1 Cl2 92.48(9) . . ?
Cl1 Cu1 Cl2 149.81(4) . . ?
C17 N4 C16 105.6(3) . . ?
C17 N4 Cu1 127.5(2) . 3_566 ?
C16 N4 Cu1 126.9(2) . 3_566 ?
C3 N1 C1 106.5(3) . . ?
C3 N1 Cu1 126.6(2) . . ?
C1 N1 Cu1 126.9(2) . . ?
C17 N3 C15 107.5(3) . . ?
C17 N3 C14 128.0(3) . . ?
C15 N3 C14 124.5(3) . . ?
C12 C5 C6 120.7(3) . . ?
C12 C5 C4 120.1(3) . . ?
C6 C5 C4 119.2(3) . . ?
C9 C8 C6 122.8(3) . . ?
C9 C8 H8 118.6 . . ?
C6 C8 H8 118.6 . . ?
N2 C4 C5 110.4(3) . . ?
N2 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C12 C11 119.8(3) . . ?
C5 C12 C13 120.5(3) . . ?
C11 C12 C13 119.7(3) . . ?
C3 N2 C2 107.4(3) . . ?
C3 N2 C4 125.9(3) . . ?
C2 N2 C4 126.7(3) . . ?
N1 C3 N2 110.4(3) . . ?
N1 C3 H3 124.8 . . ?
N2 C3 H3 124.8 . . ?
C9 C11 C12 119.8(3) . . ?
C9 C11 C14 120.4(3) . . ?
C12 C11 C14 119.6(3) . . ?
C8 C9 C11 119.0(3) . . ?
C8 C9 C10 118.8(3) . . ?
C11 C9 C10 122.1(3) . . ?
C1 C2 N2 106.4(3) . . ?
C1 C2 H2 126.8 . . ?
N2 C2 H2 126.8 . . ?
C8 C6 C5 117.8(3) . . ?
C8 C6 C7 119.4(3) . . ?
C5 C6 C7 122.8(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C14 C11 110.3(3) . . ?
N3 C14 H14A 109.6 . . ?
C11 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C11 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N4 C17 N3 111.0(3) . . ?
N4 C17 H17 124.5 . . ?
N3 C17 H17 124.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C15 N3 106.2(3) . . ?
C16 C15 H15 126.9 . . ?
N3 C15 H15 126.9 . . ?
C15 C16 N4 109.7(3) . . ?
C15 C16 H16 125.1 . . ?
N4 C16 H16 125.1 . . ?
C2 C1 N1 109.3(3) . . ?
C2 C1 H1 125.4 . . ?
N1 C1 H1 125.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C5 C4 N2 -63.1(4) . . . . ?
C6 C5 C4 N2 114.3(3) . . . . ?
C6 C5 C12 C11 -4.4(5) . . . . ?
C4 C5 C12 C11 173.0(3) . . . . ?
C6 C5 C12 C13 177.3(3) . . . . ?
C4 C5 C12 C13 -5.3(5) . . . . ?
C5 C4 N2 C3 125.1(4) . . . . ?
C5 C4 N2 C2 -51.6(5) . . . . ?
C1 N1 C3 N2 0.9(4) . . . . ?
Cu1 N1 C3 N2 -178.6(2) . . . . ?
C2 N2 C3 N1 -1.0(4) . . . . ?
C4 N2 C3 N1 -178.2(3) . . . . ?
C5 C12 C11 C9 1.6(5) . . . . ?
C13 C12 C11 C9 180.0(3) . . . . ?
C5 C12 C11 C14 -173.4(3) . . . . ?
C13 C12 C11 C14 5.0(5) . . . . ?
C6 C8 C9 C11 -3.1(5) . . . . ?
C6 C8 C9 C10 175.3(3) . . . . ?
C12 C11 C9 C8 2.0(5) . . . . ?
C14 C11 C9 C8 177.0(3) . . . . ?
C12 C11 C9 C10 -176.3(3) . . . . ?
C14 C11 C9 C10 -1.3(5) . . . . ?
C3 N2 C2 C1 0.7(4) . . . . ?
C4 N2 C2 C1 177.8(3) . . . . ?
C9 C8 C6 C5 0.4(5) . . . . ?
C9 C8 C6 C7 -180.0(3) . . . . ?
C12 C5 C6 C8 3.4(5) . . . . ?
C4 C5 C6 C8 -174.0(3) . . . . ?
C12 C5 C6 C7 -176.3(3) . . . . ?
C4 C5 C6 C7 6.3(5) . . . . ?
C17 N3 C14 C11 -131.2(4) . . . . ?
C15 N3 C14 C11 48.3(5) . . . . ?
C9 C11 C14 N3 -105.7(4) . . . . ?
C12 C11 C14 N3 69.2(4) . . . . ?
C16 N4 C17 N3 0.8(4) . . . . ?
Cu1 N4 C17 N3 178.7(2) 3_566 . . . ?
C15 N3 C17 N4 -1.0(4) . . . . ?
C14 N3 C17 N4 178.6(3) . . . . ?
C17 N3 C15 C16 0.7(4) . . . . ?
C14 N3 C15 C16 -178.8(3) . . . . ?
N3 C15 C16 N4 -0.3(4) . . . . ?
C17 N4 C16 C15 -0.3(4) . . . . ?
Cu1 N4 C16 C15 -178.3(3) 3_566 . . . ?
N2 C2 C1 N1 -0.1(5) . . . . ?
C3 N1 C1 C2 -0.5(4) . . . . ?
Cu1 N1 C1 C2 179.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4A Cl2 0.99 2.84 3.705(4) 146.8 3_576
C3 H3 Cl2 0.95 2.62 3.130(4) 113.8 .
C3 H3 Cl2 0.95 2.66 3.491(4) 146.4 3_576
C14 H14B Cl1 0.99 2.74 3.652(4) 152.7 4_576
C15 H15 Cl1 0.95 2.75 3.590(4) 148.6 3_666
C16 H16 Cl2 0.95 2.67 3.164(4) 113.3 3_566

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_CuBx_298K
_database_code_depnum_ccdc_archive 'CCDC 1566861'
_audit_update_record             
;
2017-08-04 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            CuBx_298K
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8'
_chemical_formula_sum            'C34 H40 Cl4 Cu2 N8'
_chemical_formula_weight         829.62

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/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                   8.3697(3)
_cell_length_b                   10.6009(4)
_cell_length_c                   22.4574(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.7740(10)
_cell_angle_gamma                90
_cell_volume                     1969.25(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.6575
_cell_measurement_theta_max      28.329

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    1.386
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6572
_exptl_absorpt_correction_T_max  0.7325
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31832
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.657
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4869
_reflns_number_gt                3734
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0090P)²+7.4003P] 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         4869
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0839
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_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 0.02572(7) 0.72849(6) 0.40086(3) 0.03827(17) Uani 1 1 d . . . . .
Cl1 Cl 0.16178(15) 0.69055(16) 0.32348(6) 0.0564(4) Uani 1 1 d . . . . .
Cl2 Cl -0.11912(16) 0.86308(16) 0.44946(8) 0.0682(5) Uani 1 1 d . . . . .
N4 N 0.1671(5) 0.3654(4) 0.63677(18) 0.0404(9) Uani 1 1 d . . . . .
C5 C 0.5375(5) 0.8425(4) 0.63646(19) 0.0344(10) Uani 1 1 d . . . . .
N1 N 0.2252(5) 0.7576(4) 0.45859(18) 0.0447(10) Uani 1 1 d . . . . .
C8 C 0.7630(6) 0.7590(5) 0.7028(2) 0.0423(11) Uani 1 1 d . . . . .
H8 H 0.873473 0.758896 0.716729 0.051 Uiso 1 1 calc R U . . .
N3 N 0.3273(5) 0.4960(4) 0.69376(18) 0.0421(10) Uani 1 1 d . . . . .
C12 C 0.4330(5) 0.7667(4) 0.66498(19) 0.0349(10) Uani 1 1 d . . . . .
C4 C 0.4697(6) 0.9206(5) 0.5820(2) 0.0450(12) Uani 1 1 d . . . . .
H4A H 0.386274 0.976244 0.592537 0.054 Uiso 1 1 calc R U . . .
H4B H 0.554905 0.972479 0.570145 0.054 Uiso 1 1 calc R U . . .
N2 N 0.4008(5) 0.8398(4) 0.53097(17) 0.0423(10) Uani 1 1 d . . . . .
C6 C 0.7042(5) 0.8397(5) 0.6561(2) 0.0370(10) Uani 1 1 d . . . . .
C3 C 0.2518(5) 0.8465(5) 0.5004(2) 0.0390(11) Uani 1 1 d . . . . .
H3 H 0.175619 0.906345 0.507460 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4976(6) 0.6845(4) 0.7111(2) 0.0363(10) Uani 1 1 d . . . . .
C9 C 0.6655(6) 0.6787(5) 0.7298(2) 0.0403(11) Uani 1 1 d . . . . .
C17 C 0.1756(6) 0.4542(5) 0.6778(2) 0.0397(11) Uani 1 1 d . . . . .
H17 H 0.087047 0.484559 0.693897 0.048 Uiso 1 1 calc R U . . .
C13 C 0.2509(5) 0.7732(5) 0.6451(2) 0.0480(12) Uani 1 1 d . . . . .
H13A H 0.222410 0.854884 0.628258 0.072 Uiso 1 1 calc R U . . .
H13B H 0.196562 0.759335 0.679210 0.072 Uiso 1 1 calc R U . . .
H13C H 0.218821 0.709535 0.615259 0.072 Uiso 1 1 calc R U . . .
C14 C 0.3857(7) 0.5952(5) 0.7374(2) 0.0457(12) Uani 1 1 d . . . . .
H14A H 0.442886 0.557088 0.773788 0.055 Uiso 1 1 calc R U . . .
H14B H 0.294477 0.641894 0.748038 0.055 Uiso 1 1 calc R U . . .
C2 C 0.4751(7) 0.7409(7) 0.5078(3) 0.0674(19) Uani 1 1 d . . . . .
H2 H 0.580196 0.713034 0.520420 0.081 Uiso 1 1 calc R U . . .
C10 C 0.7433(7) 0.5875(5) 0.7777(2) 0.0586(15) Uani 1 1 d . . . . .
H10A H 0.698684 0.600376 0.814105 0.088 Uiso 1 1 calc R U . . .
H10B H 0.857838 0.601997 0.785260 0.088 Uiso 1 1 calc R U . . .
H10C H 0.722652 0.502489 0.763893 0.088 Uiso 1 1 calc R U . . .
C7 C 0.8219(6) 0.9229(6) 0.6294(3) 0.0598(16) Uani 1 1 d . . . . .
H7A H 0.927114 0.916080 0.653159 0.090 Uiso 1 1 calc R U . . .
H7B H 0.786068 1.008944 0.629253 0.090 Uiso 1 1 calc R U . . .
H7C H 0.827299 0.896517 0.588867 0.090 Uiso 1 1 calc R U . . .
C15 C 0.4220(6) 0.4279(6) 0.6615(3) 0.0582(16) Uani 1 1 d . . . . .
H15 H 0.533285 0.435499 0.663118 0.070 Uiso 1 1 calc R U . . .
C16 C 0.3245(6) 0.3479(6) 0.6268(3) 0.0604(16) Uani 1 1 d . . . . .
H16 H 0.357669 0.289635 0.600207 0.072 Uiso 1 1 calc R U . . .
C1 C 0.3683(7) 0.6914(7) 0.4634(3) 0.0686(19) Uani 1 1 d . . . . .
H1 H 0.387690 0.622926 0.439629 0.082 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 N4 1.973(4) 3_566 ?
Cu1 N1 1.976(4) . ?
Cu1 Cl1 2.2543(14) . ?
Cu1 Cl2 2.2584(15) . ?
N4 C17 1.312(6) . ?
N4 C16 1.383(6) . ?
C5 C6 1.398(6) . ?
C5 C12 1.411(6) . ?
C5 C4 1.513(6) . ?
N1 C3 1.325(6) . ?
N1 C1 1.378(7) . ?
C8 C9 1.381(7) . ?
C8 C6 1.384(7) . ?
C8 H8 0.9300 . ?
N3 C17 1.341(6) . ?
N3 C15 1.360(7) . ?
N3 C14 1.470(6) . ?
C12 C11 1.398(6) . ?
C12 C13 1.523(6) . ?
C4 N2 1.476(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N2 C3 1.331(6) . ?
N2 C2 1.362(7) . ?
C6 C7 1.513(7) . ?
C3 H3 0.9300 . ?
C11 C9 1.405(7) . ?
C11 C14 1.513(7) . ?
C9 C10 1.517(7) . ?
C17 H17 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C2 C1 1.341(8) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C15 C16 1.341(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C1 H1 0.9300 . ?

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
N4 Cu1 N1 156.05(18) 3_566 . ?
N4 Cu1 Cl1 93.21(12) 3_566 . ?
N1 Cu1 Cl1 93.32(12) . . ?
N4 Cu1 Cl2 93.53(12) 3_566 . ?
N1 Cu1 Cl2 92.67(13) . . ?
Cl1 Cu1 Cl2 148.96(7) . . ?
C17 N4 C16 105.0(4) . . ?
C17 N4 Cu1 128.1(3) . 3_566 ?
C16 N4 Cu1 126.9(3) . 3_566 ?
C6 C5 C12 120.2(4) . . ?
C6 C5 C4 120.0(4) . . ?
C12 C5 C4 119.7(4) . . ?
C3 N1 C1 104.9(4) . . ?
C3 N1 Cu1 127.6(3) . . ?
C1 N1 Cu1 127.6(4) . . ?
C9 C8 C6 123.2(4) . . ?
C9 C8 H8 118.4 . . ?
C6 C8 H8 118.4 . . ?
C17 N3 C15 106.7(4) . . ?
C17 N3 C14 128.3(4) . . ?
C15 N3 C14 125.0(4) . . ?
C11 C12 C5 119.6(4) . . ?
C11 C12 C13 120.2(4) . . ?
C5 C12 C13 120.2(4) . . ?
N2 C4 C5 111.3(4) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C3 N2 C2 106.9(4) . . ?
C3 N2 C4 126.5(4) . . ?
C2 N2 C4 126.6(4) . . ?
C8 C6 C5 118.3(4) . . ?
C8 C6 C7 118.9(4) . . ?
C5 C6 C7 122.8(4) . . ?
N1 C3 N2 111.7(4) . . ?
N1 C3 H3 124.1 . . ?
N2 C3 H3 124.1 . . ?
C12 C11 C9 120.3(4) . . ?
C12 C11 C14 119.1(4) . . ?
C9 C11 C14 120.4(4) . . ?
C8 C9 C11 118.2(4) . . ?
C8 C9 C10 119.0(5) . . ?
C11 C9 C10 122.8(5) . . ?
N4 C17 N3 111.9(4) . . ?
N4 C17 H17 124.1 . . ?
N3 C17 H17 124.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C11 110.5(4) . . ?
N3 C14 H14A 109.5 . . ?
C11 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C1 C2 N2 107.1(5) . . ?
C1 C2 H2 126.5 . . ?
N2 C2 H2 126.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C15 N3 107.0(5) . . ?
C16 C15 H15 126.5 . . ?
N3 C15 H15 126.5 . . ?
C15 C16 N4 109.3(5) . . ?
C15 C16 H16 125.3 . . ?
N4 C16 H16 125.3 . . ?
C2 C1 N1 109.4(5) . . ?
C2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C5 C12 C11 -3.0(7) . . . . ?
C4 C5 C12 C11 173.2(4) . . . . ?
C6 C5 C12 C13 177.8(4) . . . . ?
C4 C5 C12 C13 -6.0(7) . . . . ?
C6 C5 C4 N2 112.1(5) . . . . ?
C12 C5 C4 N2 -64.1(6) . . . . ?
C5 C4 N2 C3 125.6(5) . . . . ?
C5 C4 N2 C2 -51.4(7) . . . . ?
C9 C8 C6 C5 1.9(7) . . . . ?
C9 C8 C6 C7 -179.4(5) . . . . ?
C12 C5 C6 C8 1.5(7) . . . . ?
C4 C5 C6 C8 -174.6(4) . . . . ?
C12 C5 C6 C7 -177.1(5) . . . . ?
C4 C5 C6 C7 6.8(7) . . . . ?
C1 N1 C3 N2 -0.3(6) . . . . ?
Cu1 N1 C3 N2 -179.2(3) . . . . ?
C2 N2 C3 N1 -0.1(6) . . . . ?
C4 N2 C3 N1 -177.6(4) . . . . ?
C5 C12 C11 C9 1.1(7) . . . . ?
C13 C12 C11 C9 -179.7(4) . . . . ?
C5 C12 C11 C14 -174.5(4) . . . . ?
C13 C12 C11 C14 4.8(7) . . . . ?
C6 C8 C9 C11 -3.7(7) . . . . ?
C6 C8 C9 C10 175.8(5) . . . . ?
C12 C11 C9 C8 2.2(7) . . . . ?
C14 C11 C9 C8 177.6(4) . . . . ?
C12 C11 C9 C10 -177.3(5) . . . . ?
C14 C11 C9 C10 -1.8(7) . . . . ?
C16 N4 C17 N3 1.2(6) . . . . ?
Cu1 N4 C17 N3 179.1(3) 3_566 . . . ?
C15 N3 C17 N4 -1.0(6) . . . . ?
C14 N3 C17 N4 179.1(5) . . . . ?
C17 N3 C14 C11 -133.1(5) . . . . ?
C15 N3 C14 C11 47.1(7) . . . . ?
C12 C11 C14 N3 70.7(6) . . . . ?
C9 C11 C14 N3 -104.8(5) . . . . ?
C3 N2 C2 C1 0.4(7) . . . . ?
C4 N2 C2 C1 177.9(5) . . . . ?
C17 N3 C15 C16 0.4(7) . . . . ?
C14 N3 C15 C16 -179.8(5) . . . . ?
N3 C15 C16 N4 0.3(8) . . . . ?
C17 N4 C16 C15 -0.9(7) . . . . ?
Cu1 N4 C16 C15 -178.8(4) 3_566 . . . ?
N2 C2 C1 N1 -0.6(8) . . . . ?
C3 N1 C1 C2 0.6(7) . . . . ?
Cu1 N1 C1 C2 179.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4A Cl2 0.97 2.85 3.706(6) 147.0 3_576
C3 H3 Cl2 0.93 2.65 3.145(5) 114.2 .
C3 H3 Cl2 0.93 2.70 3.516(5) 147.3 3_576
C14 H14B Cl1 0.97 2.80 3.676(6) 150.8 4_576
C15 H15 Cl1 0.93 2.86 3.670(6) 146.9 3_666
C16 H16 Cl2 0.93 2.68 3.161(6) 113.1 3_566

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_Cubx_PhCNSSN_298k
_database_code_depnum_ccdc_archive 'CCDC 1566863'
_audit_update_record             
;
2017-08-04 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            Cubx_phcnssn_298k
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8'
_chemical_formula_sum            'C34 H40 Cl4 Cu2 N8'
_chemical_formula_weight         829.62

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/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                   8.3927(5)
_cell_length_b                   10.8318(6)
_cell_length_c                   22.4675(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.103(2)
_cell_angle_gamma                90
_cell_volume                     2016.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      2.4575
_cell_measurement_theta_max      28.295

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.353
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5845
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28288
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.092
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4951
_reflns_number_gt                3788
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0002P)²+81.3853P] 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         4951
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2390
_refine_ls_R_factor_gt           0.2085
_refine_ls_wR_factor_ref         0.3906
_refine_ls_wR_factor_gt          0.3781
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_restrained_S_all      1.308
_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 0.0236(2) 0.73812(16) 0.39780(7) 0.0256(5) Uani 1 1 d . . . . .
Cl1 Cl 0.1587(5) 0.7010(5) 0.32032(17) 0.0458(11) Uani 1 1 d . . . . .
Cl2 Cl -0.1208(5) 0.8688(5) 0.4463(2) 0.0610(15) Uani 1 1 d . . . . .
N4 N 0.1693(15) 0.3549(13) 0.6404(6) 0.0339(15) Uani 1 1 d . . . . .
N1A N 0.212(3) 0.789(3) 0.4528(10) 0.016(5) Uiso 0.53(4) 1 d . . P A 2
C12 C 0.4288(16) 0.7620(13) 0.6645(6) 0.028(3) Uani 1 1 d . . . . .
C8 C 0.7581(19) 0.7500(15) 0.7011(7) 0.038(4) Uani 1 1 d . . . . .
H8 H 0.871448 0.747583 0.714008 0.046 Uiso 1 1 calc R U . . .
N3 N 0.3297(15) 0.4882(12) 0.6946(6) 0.0339(15) Uani 1 1 d . . . . .
C17 C 0.1776(18) 0.4455(15) 0.6798(7) 0.0339(15) Uani 1 1 d . . . . .
H17 H 0.087579 0.476878 0.695769 0.041 Uiso 1 1 calc R U . . .
N2 N 0.392(3) 0.827(3) 0.5308(13) 0.020(7) Uiso 0.47(4) 1 d . . P A 1
C13 C 0.2447(17) 0.7686(17) 0.6476(7) 0.040(4) Uani 1 1 d . . . . .
H13A H 0.213219 0.851594 0.632871 0.060 Uiso 1 1 calc R U . . .
H13B H 0.194708 0.750419 0.683233 0.060 Uiso 1 1 calc R U . . .
H13C H 0.208431 0.707955 0.616008 0.060 Uiso 1 1 calc R U . . .
C5 C 0.5293(17) 0.8368(11) 0.6368(5) 0.020(3) Uani 1 1 d . . . . .
C3 C 0.242(6) 0.836(5) 0.498(2) 0.034(14) Uiso 0.47(4) 1 d . . P A 1
H3 H 0.159386 0.893142 0.503854 0.040 Uiso 0.47(4) 1 calc R U P A 1
C11 C 0.4938(16) 0.6761(12) 0.7093(6) 0.024(3) Uani 1 1 d . . . . .
C9 C 0.6626(15) 0.6713(12) 0.7286(5) 0.021(3) Uani 1 1 d . . . . .
C14 C 0.3870(18) 0.5875(15) 0.7372(6) 0.032(3) Uani 1 1 d . . . . .
H14A H 0.448440 0.551603 0.774374 0.039 Uiso 1 1 calc R U . . .
H14B H 0.293431 0.632798 0.748210 0.039 Uiso 1 1 calc R U . . .
C6 C 0.6990(17) 0.8314(14) 0.6564(7) 0.031(3) Uani 1 1 d . . . . .
C10 C 0.747(2) 0.5796(17) 0.7723(8) 0.051(5) Uani 1 1 d . . . . .
H10A H 0.863600 0.594640 0.777856 0.077 Uiso 1 1 calc R U . . .
H10B H 0.724337 0.495940 0.756557 0.077 Uiso 1 1 calc R U . . .
H10C H 0.708578 0.587964 0.811046 0.077 Uiso 1 1 calc R U . . .
C16 C 0.3250(17) 0.3357(15) 0.6306(7) 0.0339(15) Uani 1 1 d . . . . .
H16 H 0.359175 0.275006 0.604811 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8146(19) 0.9161(17) 0.6298(9) 0.048(5) Uani 1 1 d . . . . .
H7A H 0.925030 0.901757 0.650306 0.072 Uiso 1 1 calc R U . . .
H7B H 0.784761 1.002354 0.635337 0.072 Uiso 1 1 calc R U . . .
H7C H 0.808246 0.898738 0.586695 0.072 Uiso 1 1 calc R U . . .
C4 C 0.462(2) 0.9168(16) 0.5855(7) 0.044(4) Uani 1 1 d . . . . .
H4A H 0.547528 0.970522 0.573843 0.053 Uiso 1 1 calc R U . A 1
H4B H 0.375381 0.969814 0.596679 0.053 Uiso 1 1 calc R U . A 1
C15 C 0.4218(18) 0.4191(15) 0.6645(7) 0.0339(15) Uani 1 1 d . . . . .
H15 H 0.535268 0.426768 0.666284 0.041 Uiso 1 1 calc R U . . .
C2 C 0.469(4) 0.734(3) 0.5093(13) 0.026(8) Uiso 0.47(4) 1 d . . P A 1
H2 H 0.576146 0.707704 0.523826 0.032 Uiso 0.47(4) 1 calc R U P A 1
C1 C 0.366(3) 0.684(3) 0.4626(11) 0.014(7) Uiso 0.47(4) 1 d . . P A 1
H1 H 0.385067 0.614473 0.438614 0.017 Uiso 0.47(4) 1 calc R U P A 1
C1A C 0.376(4) 0.750(4) 0.4501(17) 0.055(10) Uiso 0.53(4) 1 d . . P A 2
H1A H 0.408428 0.698969 0.419782 0.065 Uiso 0.53(4) 1 calc R U P A 2
C2A C 0.478(5) 0.800(4) 0.4996(17) 0.047(10) Uiso 0.53(4) 1 d . . P A 2
H2A H 0.591664 0.788014 0.508016 0.057 Uiso 0.53(4) 1 calc R U P A 2
N1 N 0.234(4) 0.751(4) 0.4578(15) 0.034(8) Uiso 0.47(4) 1 d . . P A 1
C3A C 0.250(4) 0.860(4) 0.5036(16) 0.018(9) Uiso 0.53(4) 1 d . . P A 2
H3A H 0.167674 0.907055 0.517837 0.022 Uiso 0.53(4) 1 calc R U P A 2
N2A N 0.394(3) 0.864(3) 0.5319(11) 0.018(6) Uiso 0.53(4) 1 d . . P A 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 N1A 1.93(2) . ?
Cu1 N4 1.984(12) 3_566 ?
Cu1 N1 2.05(3) . ?
Cu1 Cl2 2.253(5) . ?
Cu1 Cl1 2.259(4) . ?
N4 C17 1.315(19) . ?
N4 C16 1.375(18) . ?
N1A C3A 1.37(4) . ?
N1A C1A 1.45(4) . ?
C12 C5 1.387(19) . ?
C12 C11 1.41(2) . ?
C12 C13 1.534(19) . ?
C8 C6 1.37(2) . ?
C8 C9 1.38(2) . ?
C8 H8 0.9500 . ?
N3 C15 1.335(19) . ?
N3 C17 1.349(18) . ?
N3 C14 1.469(18) . ?
C17 H17 0.9500 . ?
N2 C2 1.33(4) . ?
N2 C3 1.36(6) . ?
N2 C4 1.61(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C5 C6 1.424(19) . ?
C5 C4 1.479(19) . ?
C3 N1 1.28(6) . ?
C3 H3 0.9500 . ?
C11 C9 1.415(18) . ?
C11 C14 1.515(19) . ?
C9 C10 1.49(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C6 C7 1.52(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 C15 1.36(2) . ?
C16 H16 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 N2A 1.37(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C15 H15 0.9500 . ?
C2 C1 1.37(4) . ?
C2 H2 0.9500 . ?
C1 N1 1.32(4) . ?
C1 H1 0.9500 . ?
C1A C2A 1.40(5) . ?
C1A H1A 0.9500 . ?
C2A N2A 1.29(5) . ?
C2A H2A 0.9500 . ?
C3A N2A 1.28(4) . ?
C3A H3A 0.9500 . ?

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
N1A Cu1 N4 162.5(9) . 3_566 ?
N4 Cu1 N1 151.5(12) 3_566 . ?
N1A Cu1 Cl2 87.8(8) . . ?
N4 Cu1 Cl2 93.6(4) 3_566 . ?
N1 Cu1 Cl2 96.5(10) . . ?
N1A Cu1 Cl1 94.8(7) . . ?
N4 Cu1 Cl1 92.9(4) 3_566 . ?
N1 Cu1 Cl1 91.9(9) . . ?
Cl2 Cu1 Cl1 149.1(2) . . ?
C17 N4 C16 105.7(12) . . ?
C17 N4 Cu1 128.5(10) . 3_566 ?
C16 N4 Cu1 125.9(10) . 3_566 ?
C3A N1A C1A 96(3) . . ?
C3A N1A Cu1 139(2) . . ?
C1A N1A Cu1 125(2) . . ?
C5 C12 C11 120.7(12) . . ?
C5 C12 C13 121.5(13) . . ?
C11 C12 C13 117.8(13) . . ?
C6 C8 C9 123.9(14) . . ?
C6 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
C15 N3 C17 106.4(12) . . ?
C15 N3 C14 125.8(12) . . ?
C17 N3 C14 127.7(12) . . ?
N4 C17 N3 111.7(13) . . ?
N4 C17 H17 124.1 . . ?
N3 C17 H17 124.1 . . ?
C2 N2 C3 109(3) . . ?
C2 N2 C4 126(2) . . ?
C3 N2 C4 125(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C5 C6 119.1(12) . . ?
C12 C5 C4 120.5(13) . . ?
C6 C5 C4 120.3(13) . . ?
N1 C3 N2 105(4) . . ?
N1 C3 H3 127.3 . . ?
N2 C3 H3 127.3 . . ?
C12 C11 C9 119.8(13) . . ?
C12 C11 C14 121.6(13) . . ?
C9 C11 C14 118.6(12) . . ?
C8 C9 C11 117.6(12) . . ?
C8 C9 C10 117.1(13) . . ?
C11 C9 C10 125.0(13) . . ?
N3 C14 C11 110.4(11) . . ?
N3 C14 H14A 109.6 . . ?
C11 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C11 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C8 C6 C5 118.9(14) . . ?
C8 C6 C7 119.8(14) . . ?
C5 C6 C7 121.4(14) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C16 N4 107.9(13) . . ?
C15 C16 H16 126.0 . . ?
N4 C16 H16 126.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2A C4 C5 119.5(18) . . ?
C5 C4 N2 106.8(17) . . ?
C5 C4 H4A 110.4 . . ?
N2 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
N2 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N3 C15 C16 108.2(13) . . ?
N3 C15 H15 125.9 . . ?
C16 C15 H15 125.9 . . ?
N2 C2 C1 107(3) . . ?
N2 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
N1 C1 C2 105(3) . . ?
N1 C1 H1 127.4 . . ?
C2 C1 H1 127.4 . . ?
C2A C1A N1A 109(3) . . ?
C2A C1A H1A 125.6 . . ?
N1A C1A H1A 125.6 . . ?
N2A C2A C1A 109(3) . . ?
N2A C2A H2A 125.3 . . ?
C1A C2A H2A 125.3 . . ?
C3 N1 C1 113(4) . . ?
C3 N1 Cu1 117(3) . . ?
C1 N1 Cu1 130(2) . . ?
N2A C3A N1A 120(3) . . ?
N2A C3A H3A 119.8 . . ?
N1A C3A H3A 119.8 . . ?
C3A N2A C2A 105(3) . . ?
C3A N2A C4 133(3) . . ?
C2A N2A C4 122(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N4 C17 N3 1.8(19) . . . . ?
Cu1 N4 C17 N3 -178.6(11) 3_566 . . . ?
C15 N3 C17 N4 -1.8(19) . . . . ?
C14 N3 C17 N4 -179.5(15) . . . . ?
C11 C12 C5 C6 -3.7(19) . . . . ?
C13 C12 C5 C6 176.8(13) . . . . ?
C11 C12 C5 C4 173.4(13) . . . . ?
C13 C12 C5 C4 -6(2) . . . . ?
C2 N2 C3 N1 -1(5) . . . . ?
C4 N2 C3 N1 178(3) . . . . ?
C5 C12 C11 C9 3.8(19) . . . . ?
C13 C12 C11 C9 -176.7(13) . . . . ?
C5 C12 C11 C14 -175.8(12) . . . . ?
C13 C12 C11 C14 3.7(19) . . . . ?
C6 C8 C9 C11 0(2) . . . . ?
C6 C8 C9 C10 174.1(15) . . . . ?
C12 C11 C9 C8 -1.7(19) . . . . ?
C14 C11 C9 C8 177.9(13) . . . . ?
C12 C11 C9 C10 -175.6(14) . . . . ?
C14 C11 C9 C10 4(2) . . . . ?
C15 N3 C14 C11 50(2) . . . . ?
C17 N3 C14 C11 -132.5(16) . . . . ?
C12 C11 C14 N3 74.5(17) . . . . ?
C9 C11 C14 N3 -105.1(14) . . . . ?
C9 C8 C6 C5 0(2) . . . . ?
C9 C8 C6 C7 178.8(15) . . . . ?
C12 C5 C6 C8 2(2) . . . . ?
C4 C5 C6 C8 -175.5(15) . . . . ?
C12 C5 C6 C7 -176.8(14) . . . . ?
C4 C5 C6 C7 6(2) . . . . ?
C17 N4 C16 C15 -1.2(19) . . . . ?
Cu1 N4 C16 C15 179.2(11) 3_566 . . . ?
C12 C5 C4 N2A -67(2) . . . . ?
C6 C5 C4 N2A 110(2) . . . . ?
C12 C5 C4 N2 -66(2) . . . . ?
C6 C5 C4 N2 111.0(17) . . . . ?
C2 N2 C4 C5 -51(4) . . . . ?
C3 N2 C4 C5 130(4) . . . . ?
C17 N3 C15 C16 0.9(19) . . . . ?
C14 N3 C15 C16 178.8(15) . . . . ?
N4 C16 C15 N3 0.2(19) . . . . ?
C3 N2 C2 C1 0(4) . . . . ?
C4 N2 C2 C1 -179(3) . . . . ?
N2 C2 C1 N1 2(4) . . . . ?
C3A N1A C1A C2A 2(4) . . . . ?
Cu1 N1A C1A C2A -176(2) . . . . ?
N1A C1A C2A N2A 0(5) . . . . ?
N2 C3 N1 C1 2(5) . . . . ?
N2 C3 N1 Cu1 -179(3) . . . . ?
C2 C1 N1 C3 -2(4) . . . . ?
C2 C1 N1 Cu1 179(3) . . . . ?
C1A N1A C3A N2A -4(4) . . . . ?
Cu1 N1A C3A N2A 174(2) . . . . ?
N1A C3A N2A C2A 5(4) . . . . ?
N1A C3A N2A C4 -173(3) . . . . ?
C1A C2A N2A C3A -3(4) . . . . ?
C1A C2A N2A C4 176(3) . . . . ?
C5 C4 N2A C3A 113(4) . . . . ?
C5 C4 N2A C2A -65(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 Cl2 0.95 2.51 3.10(5) 120.2 .
C3 H3 Cl2 0.95 2.85 3.63(5) 140.5 3_576
C14 H14B Cl1 0.99 2.78 3.680(16) 151.5 4_576
C16 H16 Cl2 0.95 2.65 3.145(15) 113.0 3_566
C4 H4B Cl2 0.99 2.81 3.670(19) 145.4 3_576
C15 H15 Cl1 0.95 2.89 3.718(16) 146.2 3_666
C3A H3A Cl2 0.95 2.72 3.17(4) 110.2 .
C3A H3A Cl2 0.95 2.61 3.38(4) 138.9 3_576

_refine_diff_density_max         1.195
_refine_diff_density_min         -1.763
_refine_diff_density_rms         0.221

####################################################################### 
# 
# 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_CuBx_PhCNSSN_100K
_database_code_depnum_ccdc_archive 'CCDC 1566862'
_audit_update_record             
;
2017-08-04 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            CuBx_PhCNSSN_100K
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, 0.606(C7 H5 N2 S2)'
_chemical_formula_sum            'C38.24 H43.03 Cl4 Cu2 N9.21 S1.21'
_chemical_formula_weight         939.34

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'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 '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                   8.361(3)
_cell_length_b                   10.911(4)
_cell_length_c                   22.138(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.147(5)
_cell_angle_gamma                90
_cell_volume                     1993.9(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2275
_cell_measurement_theta_min      2.4675
_cell_measurement_theta_max      26.5325

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             964.7
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    1.441
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9275
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11435
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.863
_diffrn_reflns_theta_max         28.213
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4600
_reflns_number_gt                3225
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0429P)²+1.0132P] 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         4600
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.01741(4) 0.74579(3) 0.39599(2) 0.01995(11) Uani 1 1 d . . . . .
Cl1 Cl 0.14990(10) 0.71071(9) 0.31632(3) 0.0330(2) Uani 1 1 d . . . . .
Cl2 Cl -0.12769(10) 0.87042(8) 0.44783(4) 0.0411(3) Uani 1 1 d . . . . .
C12 C 0.4278(3) 0.7528(3) 0.66631(13) 0.0171(6) Uani 1 1 d . . . . .
C8 C 0.7610(4) 0.7453(3) 0.70026(13) 0.0220(6) Uani 1 1 d . . . . .
H8 H 0.875078 0.744177 0.712831 0.026 Uiso 1 1 calc R U . . .
N4 N 0.1758(3) 0.3438(2) 0.64374(11) 0.0202(6) Uani 1 1 d . . . . .
N3 N 0.3346(3) 0.4788(2) 0.69786(11) 0.0203(6) Uani 1 1 d . . . . .
C13 C 0.2442(4) 0.7585(3) 0.64933(15) 0.0263(7) Uani 1 1 d . . . . .
H13A H 0.207289 0.693665 0.619733 0.039 Uiso 1 1 calc R U . . .
H13B H 0.212579 0.838525 0.631183 0.039 Uiso 1 1 calc R U . . .
H13C H 0.194510 0.746925 0.686150 0.039 Uiso 1 1 calc R U . . .
N2 N 0.3872(12) 0.8632(5) 0.5310(4) 0.0152(12) Uani 0.680(6) 1 d . . P A 1
C5 C 0.5277(4) 0.8304(3) 0.63810(12) 0.0165(6) Uani 1 1 d . . . . .
N1 N 0.2176(6) 0.7952(4) 0.4520(3) 0.0169(8) Uani 0.680(6) 1 d . . P A 1
C14 C 0.3916(4) 0.5795(3) 0.73935(14) 0.0237(7) Uani 1 1 d . . . . .
H14A H 0.454423 0.545821 0.777396 0.028 Uiso 1 1 calc R U . . .
H14B H 0.297192 0.624076 0.750375 0.028 Uiso 1 1 calc R U . . .
C17 C 0.1815(4) 0.4382(3) 0.68149(13) 0.0197(6) Uani 1 1 d . . . . .
H17 H 0.089560 0.472884 0.695305 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4976(4) 0.6686(3) 0.71023(13) 0.0183(6) Uani 1 1 d . . . . .
C2 C 0.4799(6) 0.8093(5) 0.4927(2) 0.0204(11) Uani 0.680(6) 1 d . . P A 1
H2 H 0.594664 0.802823 0.498700 0.024 Uiso 0.680(6) 1 calc R U P A 1
C6 C 0.6959(4) 0.8287(3) 0.65605(13) 0.0192(6) Uani 1 1 d . . . . .
C9 C 0.6665(4) 0.6631(3) 0.72702(13) 0.0211(7) Uani 1 1 d . . . . .
C3 C 0.2308(10) 0.8527(8) 0.5052(3) 0.0169(8) Uani 0.680(6) 1 d . . P A 1
H3 H 0.141917 0.882512 0.522813 0.020 Uiso 0.680(6) 1 calc R U P A 1
C4 C 0.4531(4) 0.9166(3) 0.58777(14) 0.0269(7) Uani 1 1 d . . . . .
H4A H 0.366068 0.963372 0.602924 0.032 Uiso 1 1 calc R U . A 1
H4B H 0.537156 0.976230 0.580367 0.032 Uiso 1 1 calc R U . A 1
C7 C 0.8085(4) 0.9148(3) 0.62918(15) 0.0276(7) Uani 1 1 d . . . . .
H7A H 0.920495 0.899811 0.648625 0.041 Uiso 1 1 calc R U . . .
H7B H 0.779055 0.999855 0.636514 0.041 Uiso 1 1 calc R U . . .
H7C H 0.798775 0.900464 0.585051 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7512(4) 0.5727(3) 0.77340(15) 0.0319(8) Uani 1 1 d . . . . .
H10A H 0.868530 0.586025 0.778537 0.048 Uiso 1 1 calc R U . . .
H10B H 0.726292 0.488924 0.758925 0.048 Uiso 1 1 calc R U . . .
H10C H 0.713653 0.584677 0.812720 0.048 Uiso 1 1 calc R U . . .
C15 C 0.4323(4) 0.4039(3) 0.66990(16) 0.0312(8) Uani 1 1 d . . . . .
H15 H 0.546742 0.408966 0.672870 0.037 Uiso 1 1 calc R U . . .
C16 C 0.3333(4) 0.3213(3) 0.63725(16) 0.0323(8) Uani 1 1 d . . . . .
H16 H 0.367971 0.257174 0.613337 0.039 Uiso 1 1 calc R U . . .
C1 C 0.3732(5) 0.7667(4) 0.44394(19) 0.0169(8) Uani 0.680(6) 1 d . . P A 1
H1 H 0.402023 0.724000 0.409832 0.020 Uiso 0.680(6) 1 calc R U P A 1
C2A C 0.4658(13) 0.7248(13) 0.5082(5) 0.032(3) Uani 0.320(6) 1 d . . P A 2
H2A H 0.570244 0.692006 0.522418 0.039 Uiso 0.320(6) 1 calc R U P A 2
C1A C 0.3529(11) 0.6820(10) 0.4613(4) 0.0219(18) Uani 0.320(6) 1 d . . P A 2
H1A H 0.366762 0.611885 0.437269 0.026 Uiso 0.320(6) 1 calc R U P A 2
N1A N 0.2179(14) 0.7541(9) 0.4539(5) 0.0219(18) Uani 0.320(6) 1 d . . P A 2
N2A N 0.395(3) 0.8251(13) 0.5302(10) 0.0152(12) Uani 0.320(6) 1 d . . P A 2
C3A C 0.243(2) 0.840(2) 0.4968(8) 0.0219(18) Uani 0.320(6) 1 d . . P A 2
H3A H 0.168319 0.901667 0.503359 0.026 Uiso 0.320(6) 1 calc R U P A 2
S2B S 0.1822(7) 0.4292(5) 0.4277(2) 0.0512(13) Uani 0.3029(14) 1 d . . P B -1
S1B S 0.1588(9) 0.5048(6) 0.5133(3) 0.0656(18) Uani 0.3029(14) 1 d . . P B -1
C1B C 0.436(2) 0.492(2) 0.4927(10) 0.037(4) Uani 0.3029(14) 1 d . . P B -1
N2B N 0.3741(19) 0.4470(14) 0.4376(7) 0.049(4) Uani 0.3029(14) 1 d . . P B -1
N1B N 0.351(2) 0.5249(19) 0.5329(8) 0.053(5) Uani 0.3029(14) 1 d . . P B -1
C5B C 0.9520(13) 0.5289(11) 0.5298(5) 0.048(3) Uani 0.3029(14) 1 d G . P B -1
H5B H 1.066489 0.537159 0.538381 0.058 Uiso 0.3029(14) 1 calc R U P B -1
C6B C 0.8796(15) 0.4735(14) 0.4758(5) 0.040(4) Uani 0.3029(14) 1 d G . P B -1
H6B H 0.944570 0.443816 0.447459 0.048 Uiso 0.3029(14) 1 calc R U P B -1
C2B C 0.7121(16) 0.4614(19) 0.4633(7) 0.040(4) Uani 0.3029(14) 1 d G . P B -1
H2B H 0.662572 0.423494 0.426391 0.048 Uiso 0.3029(14) 1 calc R U P B -1
C3B C 0.6170(12) 0.505(2) 0.5048(9) 0.040(4) Uani 0.3029(14) 1 d G . P B -1
C7B C 0.6894(17) 0.5602(19) 0.5588(8) 0.048(3) Uani 0.3029(14) 1 d G . P B -1
H7B1 H 0.624407 0.589860 0.587167 0.058 Uiso 0.3029(14) 1 calc R U P B -1
C4B C 0.8569(18) 0.5723(15) 0.5713(5) 0.048(3) Uani 0.3029(14) 1 d G . P B -1
H4B1 H 0.906405 0.610182 0.608236 0.058 Uiso 0.3029(14) 1 calc R U P B -1


_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 N1A 1.944(11) . ?
Cu1 N4 1.971(3) 3_566 ?
Cu1 N1 1.992(5) . ?
Cu1 Cl2 2.2541(10) . ?
Cu1 Cl1 2.2595(11) . ?
C12 C11 1.396(4) . ?
C12 C5 1.404(4) . ?
C12 C13 1.522(4) . ?
C8 C6 1.383(4) . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
N4 C17 1.322(4) . ?
N4 C16 1.370(4) . ?
N3 C17 1.349(4) . ?
N3 C15 1.371(4) . ?
N3 C14 1.463(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N2 C3 1.346(13) . ?
N2 C2 1.370(10) . ?
N2 C4 1.415(9) . ?
C5 C6 1.399(4) . ?
C5 C4 1.515(4) . ?
N1 C3 1.324(8) . ?
N1 C1 1.377(7) . ?
C14 C11 1.526(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 H17 0.9500 . ?
C11 C9 1.403(4) . ?
C2 C1 1.368(6) . ?
C2 H2 0.9500 . ?
C6 C7 1.517(4) . ?
C9 C10 1.516(4) . ?
C3 H3 0.9500 . ?
C4 N2A 1.631(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C15 C16 1.352(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C1 H1 0.9500 . ?
C2A N2A 1.37(2) . ?
C2A C1A 1.369(14) . ?
C2A H2A 0.9500 . ?
C1A N1A 1.364(14) . ?
C1A H1A 0.9500 . ?
N1A C3A 1.324(17) . ?
N2A C3A 1.37(3) . ?
C3A H3A 0.9500 . ?
S2B N2B 1.597(14) . ?
S2B S1B 2.102(6) . ?
S1B N1B 1.614(15) . ?
C1B N1B 1.276(18) . ?
C1B N2B 1.340(18) . ?
C1B C3B 1.500(17) . ?
C5B C6B 1.3900 . ?
C5B C4B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B C2B 1.3900 . ?
C6B H6B 0.9500 . ?
C2B C3B 1.3900 . ?
C2B H2B 0.9500 . ?
C3B C7B 1.3900 . ?
C7B C4B 1.3900 . ?
C7B H7B1 0.9500 . ?
C4B H4B1 0.9500 . ?

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
N1A Cu1 N4 151.2(3) . 3_566 ?
N4 Cu1 N1 163.62(14) 3_566 . ?
N1A Cu1 Cl2 96.5(3) . . ?
N4 Cu1 Cl2 93.28(8) 3_566 . ?
N1 Cu1 Cl2 89.25(16) . . ?
N1A Cu1 Cl1 92.6(4) . . ?
N4 Cu1 Cl1 92.09(8) 3_566 . ?
N1 Cu1 Cl1 93.67(17) . . ?
Cl2 Cu1 Cl1 150.45(4) . . ?
C11 C12 C5 119.6(3) . . ?
C11 C12 C13 119.5(3) . . ?
C5 C12 C13 120.9(3) . . ?
C6 C8 C9 122.7(3) . . ?
C6 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C17 N4 C16 105.5(3) . . ?
C17 N4 Cu1 127.8(2) . 3_566 ?
C16 N4 Cu1 126.7(2) . 3_566 ?
C17 N3 C15 106.9(3) . . ?
C17 N3 C14 128.0(3) . . ?
C15 N3 C14 125.0(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 N2 C2 107.9(6) . . ?
C3 N2 C4 128.8(7) . . ?
C2 N2 C4 123.3(7) . . ?
C6 C5 C12 120.5(3) . . ?
C6 C5 C4 119.6(3) . . ?
C12 C5 C4 119.8(3) . . ?
C3 N1 C1 106.0(5) . . ?
C3 N1 Cu1 128.7(5) . . ?
C1 N1 Cu1 125.2(4) . . ?
N3 C14 C11 111.5(2) . . ?
N3 C14 H14A 109.3 . . ?
C11 C14 H14A 109.3 . . ?
N3 C14 H14B 109.3 . . ?
C11 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N4 C17 N3 111.3(3) . . ?
N4 C17 H17 124.4 . . ?
N3 C17 H17 124.4 . . ?
C12 C11 C9 120.3(3) . . ?
C12 C11 C14 120.4(3) . . ?
C9 C11 C14 119.2(3) . . ?
C1 C2 N2 105.8(5) . . ?
C1 C2 H2 127.1 . . ?
N2 C2 H2 127.1 . . ?
C8 C6 C5 118.3(3) . . ?
C8 C6 C7 119.1(3) . . ?
C5 C6 C7 122.6(3) . . ?
C8 C9 C11 118.5(3) . . ?
C8 C9 C10 118.2(3) . . ?
C11 C9 C10 123.3(3) . . ?
N1 C3 N2 110.9(6) . . ?
N1 C3 H3 124.6 . . ?
N2 C3 H3 124.6 . . ?
N2 C4 C5 117.0(3) . . ?
C5 C4 N2A 103.3(6) . . ?
N2 C4 H4A 108.0 . . ?
C5 C4 H4A 108.0 . . ?
N2 C4 H4B 108.0 . . ?
C5 C4 H4B 108.0 . . ?
H4A C4 H4B 107.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C15 N3 106.3(3) . . ?
C16 C15 H15 126.9 . . ?
N3 C15 H15 126.9 . . ?
C15 C16 N4 110.0(3) . . ?
C15 C16 H16 125.0 . . ?
N4 C16 H16 125.0 . . ?
C2 C1 N1 109.4(4) . . ?
C2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?
N2A C2A C1A 105.0(13) . . ?
N2A C2A H2A 127.5 . . ?
C1A C2A H2A 127.5 . . ?
N1A C1A C2A 110.6(9) . . ?
N1A C1A H1A 124.7 . . ?
C2A C1A H1A 124.7 . . ?
C3A N1A C1A 106.5(11) . . ?
C3A N1A Cu1 122.0(9) . . ?
C1A N1A Cu1 131.5(8) . . ?
C2A N2A C3A 108.3(16) . . ?
C2A N2A C4 132.6(16) . . ?
C3A N2A C4 118.9(14) . . ?
N1A C3A N2A 109.5(13) . . ?
N1A C3A H3A 125.2 . . ?
N2A C3A H3A 125.2 . . ?
N2B S2B S1B 93.7(5) . . ?
N1B S1B S2B 93.7(6) . . ?
N1B C1B N2B 124.2(16) . . ?
N1B C1B C3B 120.3(11) . . ?
N2B C1B C3B 115.5(14) . . ?
C1B N2B S2B 113.8(13) . . ?
C1B N1B S1B 114.5(11) . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C2B C6B C5B 120.0 . . ?
C2B C6B H6B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C3B C2B C6B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C6B C2B H2B 120.0 . . ?
C2B C3B C7B 120.0 . . ?
C2B C3B C1B 121.1(8) . . ?
C7B C3B C1B 118.9(8) . . ?
C3B C7B C4B 120.0 . . ?
C3B C7B H7B1 120.0 . . ?
C4B C7B H7B1 120.0 . . ?
C7B C4B C5B 120.0 . . ?
C7B C4B H4B1 120.0 . . ?
C5B C4B H4B1 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C12 C5 C6 -3.6(4) . . . . ?
C13 C12 C5 C6 176.9(3) . . . . ?
C11 C12 C5 C4 176.4(3) . . . . ?
C13 C12 C5 C4 -3.1(4) . . . . ?
C17 N3 C14 C11 -128.9(3) . . . . ?
C15 N3 C14 C11 53.9(4) . . . . ?
C16 N4 C17 N3 1.8(3) . . . . ?
Cu1 N4 C17 N3 -177.65(19) 3_566 . . . ?
C15 N3 C17 N4 -1.4(3) . . . . ?
C14 N3 C17 N4 -179.0(3) . . . . ?
C5 C12 C11 C9 1.3(4) . . . . ?
C13 C12 C11 C9 -179.2(3) . . . . ?
C5 C12 C11 C14 -177.2(3) . . . . ?
C13 C12 C11 C14 2.3(4) . . . . ?
N3 C14 C11 C12 76.5(3) . . . . ?
N3 C14 C11 C9 -102.0(3) . . . . ?
C3 N2 C2 C1 -0.2(7) . . . . ?
C4 N2 C2 C1 178.6(5) . . . . ?
C9 C8 C6 C5 0.4(4) . . . . ?
C9 C8 C6 C7 -179.8(3) . . . . ?
C12 C5 C6 C8 2.7(4) . . . . ?
C4 C5 C6 C8 -177.3(3) . . . . ?
C12 C5 C6 C7 -177.0(3) . . . . ?
C4 C5 C6 C7 3.0(4) . . . . ?
C6 C8 C9 C11 -2.7(4) . . . . ?
C6 C8 C9 C10 177.9(3) . . . . ?
C12 C11 C9 C8 1.8(4) . . . . ?
C14 C11 C9 C8 -179.7(3) . . . . ?
C12 C11 C9 C10 -178.8(3) . . . . ?
C14 C11 C9 C10 -0.3(4) . . . . ?
C1 N1 C3 N2 0.7(9) . . . . ?
Cu1 N1 C3 N2 176.3(5) . . . . ?
C2 N2 C3 N1 -0.3(9) . . . . ?
C4 N2 C3 N1 -179.0(6) . . . . ?
C3 N2 C4 C5 109.6(8) . . . . ?
C2 N2 C4 C5 -68.9(8) . . . . ?
C6 C5 C4 N2 109.2(6) . . . . ?
C12 C5 C4 N2 -70.8(6) . . . . ?
C6 C5 C4 N2A 107.9(9) . . . . ?
C12 C5 C4 N2A -72.1(10) . . . . ?
C17 N3 C15 C16 0.5(4) . . . . ?
C14 N3 C15 C16 178.2(3) . . . . ?
N3 C15 C16 N4 0.6(4) . . . . ?
C17 N4 C16 C15 -1.4(4) . . . . ?
Cu1 N4 C16 C15 178.0(2) 3_566 . . . ?
N2 C2 C1 N1 0.6(6) . . . . ?
C3 N1 C1 C2 -0.8(7) . . . . ?
Cu1 N1 C1 C2 -176.7(3) . . . . ?
N2A C2A C1A N1A 0.7(17) . . . . ?
C2A C1A N1A C3A -1.6(17) . . . . ?
C2A C1A N1A Cu1 179.1(9) . . . . ?
C1A C2A N2A C3A 0(2) . . . . ?
C1A C2A N2A C4 175.9(18) . . . . ?
C5 C4 N2A C2A -41(2) . . . . ?
C5 C4 N2A C3A 134.3(16) . . . . ?
C1A N1A C3A N2A 2(2) . . . . ?
Cu1 N1A C3A N2A -178.8(12) . . . . ?
C2A N2A C3A N1A -1(2) . . . . ?
C4 N2A C3A N1A -177.6(15) . . . . ?
N1B C1B N2B S2B -4.0(18) . . . . ?
C3B C1B N2B S2B 177.4(7) . . . . ?
S1B S2B N2B C1B 3.4(11) . . . . ?
N2B C1B N1B S1B 1.8(18) . . . . ?
C3B C1B N1B S1B -179.7(9) . . . . ?
S2B S1B N1B C1B 0.7(10) . . . . ?
C4B C5B C6B C2B 0.0 . . . . ?
C5B C6B C2B C3B 0.0 . . . . ?
C6B C2B C3B C7B 0.0 . . . . ?
C6B C2B C3B C1B -179.4(11) . . . . ?
N1B C1B C3B C2B 175.5(14) . . . . ?
N2B C1B C3B C2B -5.9(19) . . . . ?
N1B C1B C3B C7B -4.0(16) . . . . ?
N2B C1B C3B C7B 174.6(17) . . . . ?
C2B C3B C7B C4B 0.0 . . . . ?
C1B C3B C7B C4B 179.5(11) . . . . ?
C3B C7B C4B C5B 0.0 . . . . ?
C6B C5B C4B C7B 0.0 . . . . ?

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
C14 H14B Cl1 0.99 2.73 3.650(3) 154.2 4_576
C2 H2 Cl2 0.95 2.83 3.637(5) 142.9 1_655
C3 H3 Cl2 0.95 2.58 3.070(9) 112.3 .
C3 H3 Cl2 0.95 2.78 3.352(8) 119.6 3_576
C4 H4A Cl2 0.99 2.79 3.569(4) 135.5 3_576
C15 H15 Cl1 0.95 2.83 3.677(4) 149.1 3_666
C16 H16 Cl2 0.95 2.63 3.139(3) 113.6 3_566
C1 H1 Cl1 0.95 2.71 3.188(4) 111.6 .
C3A H3A Cl2 0.95 2.60 3.138(19) 115.9 .
C3A H3A Cl2 0.95 2.75 3.581(18) 146.0 3_576

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.086

