# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1818828'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            1
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H48 Cl4 Cu2 N8 O2 S2'
_chemical_formula_sum            'C36 H48 Cl4 Cu2 N8 O2 S2'
_chemical_formula_weight         957.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.8724(19)
_cell_length_b                   13.043(3)
_cell_length_c                   17.770(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.506(3)
_cell_angle_gamma                90
_cell_volume                     2046.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    764
_cell_measurement_theta_min      2.303
_cell_measurement_theta_max      21.4915

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    1.446
_shelx_estimated_absorpt_T_min   0.719
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6702
_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  graphite
_diffrn_measurement_method       'Bruker APEX CCD area -detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12728
_diffrn_reflns_av_unetI/netI     0.1162
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.940
_diffrn_reflns_theta_max         28.200
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4749
_reflns_number_gt                3140
_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    'SHELXS-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         4749
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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 0.27922(6) 0.71924(4) 0.09437(3) 0.01334(15) Uani 1 1 d . . . . .
Cl2 Cl 0.17991(12) 0.63141(8) 0.19527(6) 0.0156(2) Uani 1 1 d . . . . .
Cl1 Cl 0.49687(12) 0.66622(9) 0.04413(6) 0.0205(3) Uani 1 1 d . . . . .
S1 S 0.26661(13) 0.92391(9) -0.01624(7) 0.0201(3) Uani 1 1 d . . . . .
O1 O 0.1684(4) 0.8670(2) 0.03482(18) 0.0219(8) Uani 1 1 d . . . . .
C16 C 0.0982(5) 1.2786(3) -0.0547(3) 0.0176(10) Uani 1 1 d . . . . .
H16A H 0.125291 1.213081 -0.030041 0.026 Uiso 1 1 calc R U . . .
H16B H 0.190592 1.316881 -0.062304 0.026 Uiso 1 1 calc R U . . .
H16C H 0.040985 1.265804 -0.103773 0.026 Uiso 1 1 calc R U . . .
N4 N -0.1453(4) 1.3512(3) -0.0165(2) 0.0133(8) Uani 1 1 d . . . . .
N3 N 0.0615(4) 1.3927(3) 0.0549(2) 0.0139(8) Uani 1 1 d . . . . .
N2 N 0.4266(4) 0.9554(2) 0.2361(2) 0.0140(8) Uani 1 1 d . . . . .
N1 N 0.3870(4) 0.8225(3) 0.1606(2) 0.0141(8) Uani 1 1 d . . . . .
C1 C 0.5390(5) 0.8482(3) 0.1652(3) 0.0164(10) Uani 1 1 d . . . . .
H1 H 0.614175 0.813838 0.140154 0.020 Uiso 1 1 calc R U . . .
C15 C 0.0046(5) 1.3389(3) -0.0067(2) 0.0135(9) Uani 1 1 d . . . . .
C3 C 0.3218(5) 0.8886(3) 0.2042(2) 0.0141(9) Uani 1 1 d . . . . .
C2 C 0.5629(5) 0.9303(3) 0.2113(2) 0.0158(10) Uani 1 1 d . . . . .
H2 H 0.656745 0.964107 0.223939 0.019 Uiso 1 1 calc R U . . .
C12 C 0.2191(5) 1.3933(3) 0.0872(3) 0.0157(10) Uani 1 1 d . . . . .
H12A H 0.237833 1.456299 0.117717 0.019 Uiso 1 1 calc R U . . .
H12B H 0.285614 1.395545 0.045540 0.019 Uiso 1 1 calc R U . . .
C13 C -0.0565(5) 1.4405(3) 0.0852(3) 0.0160(10) Uani 1 1 d . . . . .
H13 H -0.050432 1.482921 0.128880 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2611(5) 1.3011(3) 0.1364(2) 0.0121(9) Uani 1 1 d . . . . .
C6 C 0.3485(5) 1.1371(3) 0.2316(2) 0.0149(10) Uani 1 1 d . . . . .
C8 C 0.1574(5) 1.2530(3) 0.1770(3) 0.0185(10) Uani 1 1 d . . . . .
H8 H 0.055242 1.275769 0.172393 0.022 Uiso 1 1 calc R U . . .
C14 C -0.1833(5) 1.4152(3) 0.0406(2) 0.0147(10) Uani 1 1 d . . . . .
H14 H -0.282821 1.437853 0.047442 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4106(5) 1.2661(3) 0.1429(2) 0.0157(10) Uani 1 1 d . . . . .
H10 H 0.483267 1.298112 0.114732 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3977(5) 1.0462(3) 0.2816(3) 0.0202(11) Uani 1 1 d . . . . .
H5A H 0.490847 1.064278 0.314019 0.024 Uiso 1 1 calc R U . . .
H5B H 0.317561 1.030233 0.314881 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4529(5) 1.1851(3) 0.1904(2) 0.0158(10) Uani 1 1 d . . . . .
H11 H 0.554964 1.161980 0.194857 0.019 Uiso 1 1 calc R U . . .
C7 C 0.2001(5) 1.1711(3) 0.2251(2) 0.0158(10) Uani 1 1 d . . . . .
H7 H 0.127509 1.138819 0.253160 0.019 Uiso 1 1 calc R U . . .
C17 C 0.3153(5) 1.0412(3) 0.0309(3) 0.0233(11) Uani 1 1 d . . . . .
H17A H 0.224160 1.072371 0.048036 0.035 Uiso 1 1 calc R U . . .
H17B H 0.359868 1.088014 -0.004026 0.035 Uiso 1 1 calc R U . . .
H17C H 0.388818 1.027841 0.074514 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1589(5) 0.8938(3) 0.2173(3) 0.0192(10) Uani 1 1 d . . . . .
H4A H 0.119086 0.962007 0.203344 0.029 Uiso 1 1 calc R U . . .
H4B H 0.147843 0.881059 0.270872 0.029 Uiso 1 1 calc R U . . .
H4C H 0.102347 0.841827 0.186413 0.029 Uiso 1 1 calc R U . . .
C18 C 0.1380(6) 0.9733(4) -0.0906(3) 0.0294(12) Uani 1 1 d . . . . .
H18A H 0.095863 0.916598 -0.122121 0.044 Uiso 1 1 calc R U . . .
H18B H 0.191538 1.020657 -0.121524 0.044 Uiso 1 1 calc R U . . .
H18C H 0.055705 1.009779 -0.068960 0.044 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 1.963(3) 3_575 ?
Cu1 N1 1.974(3) . ?
Cu1 Cl1 2.3099(13) . ?
Cu1 O1 2.367(3) . ?
Cu1 Cl2 2.3678(13) . ?
S1 O1 1.512(3) . ?
S1 C17 1.777(4) . ?
S1 C18 1.781(5) . ?
C16 C15 1.474(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N4 C15 1.334(5) . ?
N4 C14 1.380(5) . ?
N3 C15 1.357(5) . ?
N3 C13 1.373(5) . ?
N3 C12 1.459(5) . ?
N2 C3 1.357(5) . ?
N2 C2 1.367(6) . ?
N2 C5 1.470(5) . ?
N1 C3 1.329(5) . ?
N1 C1 1.384(5) . ?
C1 C2 1.351(6) . ?
C1 H1 0.9500 . ?
C3 C4 1.488(6) . ?
C2 H2 0.9500 . ?
C12 C9 1.513(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.354(6) . ?
C13 H13 0.9500 . ?
C9 C8 1.375(6) . ?
C9 C10 1.397(6) . ?
C6 C7 1.384(6) . ?
C6 C11 1.384(6) . ?
C6 C5 1.519(6) . ?
C8 C7 1.397(6) . ?
C8 H8 0.9500 . ?
C14 H14 0.9500 . ?
C10 C11 1.382(6) . ?
C10 H10 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 H11 0.9500 . ?
C7 H7 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 164.82(14) 3_575 . ?
N4 Cu1 Cl1 93.41(11) 3_575 . ?
N1 Cu1 Cl1 93.41(11) . . ?
N4 Cu1 O1 82.44(12) 3_575 . ?
N1 Cu1 O1 82.40(12) . . ?
Cl1 Cu1 O1 113.44(9) . . ?
N4 Cu1 Cl2 93.63(11) 3_575 . ?
N1 Cu1 Cl2 94.17(11) . . ?
Cl1 Cu1 Cl2 122.24(5) . . ?
O1 Cu1 Cl2 124.31(9) . . ?
O1 S1 C17 105.5(2) . . ?
O1 S1 C18 104.9(2) . . ?
C17 S1 C18 98.5(2) . . ?
S1 O1 Cu1 115.42(18) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 N4 C14 106.7(3) . . ?
C15 N4 Cu1 124.4(3) . 3_575 ?
C14 N4 Cu1 128.8(3) . 3_575 ?
C15 N3 C13 108.2(4) . . ?
C15 N3 C12 126.0(4) . . ?
C13 N3 C12 125.6(4) . . ?
C3 N2 C2 107.7(4) . . ?
C3 N2 C5 126.7(4) . . ?
C2 N2 C5 125.2(4) . . ?
C3 N1 C1 106.5(4) . . ?
C3 N1 Cu1 125.3(3) . . ?
C1 N1 Cu1 127.9(3) . . ?
C2 C1 N1 108.9(4) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
N4 C15 N3 109.5(4) . . ?
N4 C15 C16 126.7(4) . . ?
N3 C15 C16 123.8(4) . . ?
N1 C3 N2 110.0(4) . . ?
N1 C3 C4 127.2(4) . . ?
N2 C3 C4 122.8(4) . . ?
C1 C2 N2 107.0(4) . . ?
C1 C2 H2 126.5 . . ?
N2 C2 H2 126.5 . . ?
N3 C12 C9 113.4(4) . . ?
N3 C12 H12A 108.9 . . ?
C9 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C9 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 N3 106.3(4) . . ?
C14 C13 H13 126.8 . . ?
N3 C13 H13 126.8 . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 C12 121.8(4) . . ?
C10 C9 C12 119.1(4) . . ?
C7 C6 C11 119.4(4) . . ?
C7 C6 C5 121.1(4) . . ?
C11 C6 C5 119.5(4) . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C13 C14 N4 109.3(4) . . ?
C13 C14 H14 125.4 . . ?
N4 C14 H14 125.4 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
N2 C5 C6 111.3(3) . . ?
N2 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C10 C11 C6 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C6 C7 C8 119.7(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C17 S1 O1 Cu1 -110.4(2) . . . . ?
C18 S1 O1 Cu1 146.1(2) . . . . ?
C3 N1 C1 C2 -0.5(5) . . . . ?
Cu1 N1 C1 C2 173.1(3) . . . . ?
C14 N4 C15 N3 0.3(5) . . . . ?
Cu1 N4 C15 N3 -175.8(3) 3_575 . . . ?
C14 N4 C15 C16 -178.6(4) . . . . ?
Cu1 N4 C15 C16 5.4(6) 3_575 . . . ?
C13 N3 C15 N4 0.2(5) . . . . ?
C12 N3 C15 N4 175.6(4) . . . . ?
C13 N3 C15 C16 179.1(4) . . . . ?
C12 N3 C15 C16 -5.5(7) . . . . ?
C1 N1 C3 N2 0.1(5) . . . . ?
Cu1 N1 C3 N2 -173.7(3) . . . . ?
C1 N1 C3 C4 179.1(4) . . . . ?
Cu1 N1 C3 C4 5.3(6) . . . . ?
C2 N2 C3 N1 0.3(5) . . . . ?
C5 N2 C3 N1 173.2(4) . . . . ?
C2 N2 C3 C4 -178.8(4) . . . . ?
C5 N2 C3 C4 -5.8(6) . . . . ?
N1 C1 C2 N2 0.6(5) . . . . ?
C3 N2 C2 C1 -0.5(5) . . . . ?
C5 N2 C2 C1 -173.7(4) . . . . ?
C15 N3 C12 C9 -80.1(5) . . . . ?
C13 N3 C12 C9 94.5(5) . . . . ?
C15 N3 C13 C14 -0.6(5) . . . . ?
C12 N3 C13 C14 -176.0(4) . . . . ?
N3 C12 C9 C8 -31.0(6) . . . . ?
N3 C12 C9 C10 151.5(4) . . . . ?
C10 C9 C8 C7 0.8(6) . . . . ?
C12 C9 C8 C7 -176.8(4) . . . . ?
N3 C13 C14 N4 0.8(5) . . . . ?
C15 N4 C14 C13 -0.6(5) . . . . ?
Cu1 N4 C14 C13 175.2(3) 3_575 . . . ?
C8 C9 C10 C11 -0.7(6) . . . . ?
C12 C9 C10 C11 176.9(4) . . . . ?
C3 N2 C5 C6 -81.7(5) . . . . ?
C2 N2 C5 C6 90.1(5) . . . . ?
C7 C6 C5 N2 107.4(5) . . . . ?
C11 C6 C5 N2 -70.8(5) . . . . ?
C9 C10 C11 C6 0.4(6) . . . . ?
C7 C6 C11 C10 -0.1(6) . . . . ?
C5 C6 C11 C10 178.2(4) . . . . ?
C11 C6 C7 C8 0.1(6) . . . . ?
C5 C6 C7 C8 -178.2(4) . . . . ?
C9 C8 C7 C6 -0.5(7) . . . . ?

_refine_diff_density_max         0.639
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.140



####################################################################### 
# 
# 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_5_343K
_database_code_depnum_ccdc_archive 'CCDC 1818831'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            5_343K
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H36 Cl4 Cu2 N8, 0.472(C8 H20 O)'
_chemical_formula_sum            'C35.78 H45.44 Cl4 Cu2 N8 O0.47'
_chemical_formula_weight         863.94

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6706(8)
_cell_length_b                   13.3945(12)
_cell_length_c                   18.2327(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.236(3)
_cell_angle_gamma                90.00
_cell_volume                     2108.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    343(2)
_cell_measurement_reflns_used    7749
_cell_measurement_theta_min      2.275
_cell_measurement_theta_max      28.136

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             891.7
_exptl_absorpt_coefficient_mu    1.298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, 2012'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      343(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            31310
_diffrn_reflns_av_R_equivalents  0.2270
_diffrn_reflns_av_sigmaI/netI    0.1397
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.35
_reflns_number_total             5254
_reflns_number_gt                2236
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)²+6.0982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    Constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5254
_refine_ls_number_parameters     228
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2449
_refine_ls_R_factor_gt           0.1067
_refine_ls_wR_factor_ref         0.2767
_refine_ls_wR_factor_gt          0.2085
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.097
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.29046(11) 0.68955(7) 0.10509(5) 0.0637(4) Uani 1 1 d . . .
Cl2 Cl 0.5078(3) 0.6342(2) 0.05974(13) 0.0895(8) Uani 1 1 d . . .
N1 N 0.3849(8) 0.8070(5) 0.1584(4) 0.0738(19) Uani 1 1 d . . .
N3 N 0.0601(7) 1.3823(5) 0.0545(3) 0.0630(17) Uani 1 1 d . . .
N4 N -0.1503(7) 1.3532(5) -0.0203(3) 0.0593(16) Uani 1 1 d . . .
N2 N 0.4248(9) 0.9416(5) 0.2232(4) 0.0734(19) Uani 1 1 d . . .
C15 C 0.0003(10) 1.3352(6) -0.0080(4) 0.062(2) Uani 1 1 d . . .
C14 C -0.1873(10) 1.4164(7) 0.0362(4) 0.072(2) Uani 1 1 d . . .
H14 H -0.2854 1.4417 0.0419 0.086 Uiso 1 1 calc R . .
C16 C 0.0953(10) 1.2732(7) -0.0536(5) 0.086(3) Uani 1 1 d . . .
H16A H 0.0384 1.2602 -0.1003 0.130 Uiso 1 1 calc R . .
H16B H 0.1200 1.2112 -0.0289 0.130 Uiso 1 1 calc R . .
H16C H 0.1892 1.3081 -0.0613 0.130 Uiso 1 1 calc R . .
C1 C 0.5404(12) 0.8324(8) 0.1601(6) 0.095(3) Uani 1 1 d . . .
H1 H 0.6160 0.7974 0.1377 0.114 Uiso 1 1 calc R . .
C2 C 0.5618(13) 0.9150(9) 0.1990(6) 0.101(3) Uani 1 1 d . . .
H2 H 0.6550 0.9491 0.2082 0.121 Uiso 1 1 calc R . .
C4 C 0.1577(14) 0.8798(9) 0.2107(8) 0.134(5) Uani 1 1 d . . .
H4A H 0.1507 0.9111 0.2577 0.201 Uiso 1 1 calc R . .
H4B H 0.1149 0.8137 0.2116 0.201 Uiso 1 1 calc R . .
H4C H 0.1007 0.9183 0.1730 0.201 Uiso 1 1 calc R . .
C9 C 0.2621(10) 1.2872(6) 0.1307(4) 0.060(2) Uani 1 1 d . . .
C12 C 0.2206(9) 1.3808(6) 0.0863(5) 0.072(2) Uani 1 1 d . . .
H12A H 0.2390 1.4387 0.1178 0.086 Uiso 1 1 calc R . .
H12B H 0.2881 1.3860 0.0469 0.086 Uiso 1 1 calc R . .
C6 C 0.3517(11) 1.1223(6) 0.2171(5) 0.069(2) Uani 1 1 d . . .
C7 C 0.4530(11) 1.1690(8) 0.1759(5) 0.088(3) Uani 1 1 d . . .
H7 H 0.5538 1.1451 0.1767 0.105 Uiso 1 1 calc R . .
C10 C 0.1600(12) 1.2402(8) 0.1716(6) 0.091(3) Uani 1 1 d . . .
H10 H 0.0584 1.2627 0.1705 0.109 Uiso 1 1 calc R . .
C11 C 0.2083(13) 1.1579(8) 0.2153(6) 0.094(3) Uani 1 1 d . . .
H11 H 0.1381 1.1274 0.2437 0.113 Uiso 1 1 calc R . .
C8 C 0.4100(11) 1.2517(8) 0.1323(5) 0.087(3) Uani 1 1 d . . .
H8 H 0.4814 1.2824 0.1046 0.105 Uiso 1 1 calc R . .
C5 C 0.4015(13) 1.0329(7) 0.2648(5) 0.095(3) Uani 1 1 d . . .
H5A H 0.4973 1.0492 0.2940 0.114 Uiso 1 1 calc R . .
H5B H 0.3234 1.0203 0.2985 0.114 Uiso 1 1 calc R . .
C3 C 0.3214(11) 0.8739(7) 0.1953(5) 0.075(2) Uani 1 1 d . . .
C13 C -0.0586(10) 1.4352(7) 0.0817(5) 0.076(2) Uani 1 1 d . . .
H13 H -0.0515 1.4760 0.1231 0.091 Uiso 1 1 calc R . .
Cl1 Cl 0.1657(3) 0.61916(18) 0.19643(12) 0.0787(7) Uani 1 1 d . . .
C3A C -0.098(3) 1.039(5) 0.0470(19) 0.31(3) Uiso 0.472(15) 1 d PD A -1
H3A1 H -0.0680 1.1081 0.0572 0.376 Uiso 0.472(15) 1 calc PR A -1
H3A2 H -0.0844 1.0030 0.0931 0.376 Uiso 0.472(15) 1 calc PR A -1
O1A O 0.0000 1.0000 0.0000 0.143(11) Uiso 0.472(15) 2 d SPD . .
C2A C 0.1537(17) 0.983(5) 0.019(2) 0.31(3) Uiso 0.472(15) 1 d PD A -1
H2A1 H 0.1661 0.9474 0.0659 0.376 Uiso 0.472(15) 1 calc PR A -1
H2A2 H 0.2084 1.0456 0.0252 0.376 Uiso 0.472(15) 1 calc PR A -1
C4A C -0.271(4) 1.037(7) 0.019(4) 0.33(4) Uiso 0.472(15) 1 d PD A -1
H4A1 H -0.3309 1.0660 0.0556 0.499 Uiso 0.472(15) 1 calc PR A -1
H4A2 H -0.3035 0.9697 0.0097 0.499 Uiso 0.472(15) 1 calc PR A -1
H4A3 H -0.2874 1.0754 -0.0257 0.499 Uiso 0.472(15) 1 calc PR A -1
C1A C 0.223(8) 0.920(7) -0.041(3) 0.39(6) Uiso 0.472(15) 1 d PD A -1
H1A1 H 0.3306 0.9071 -0.0260 0.584 Uiso 0.472(15) 1 calc PR A -1
H1A2 H 0.2138 0.9557 -0.0863 0.584 Uiso 0.472(15) 1 calc PR A -1
H1A3 H 0.1686 0.8575 -0.0466 0.584 Uiso 0.472(15) 1 calc PR A -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 N4 1.963(6) 3_575 ?
Cu1 N1 1.986(7) . ?
Cu1 Cl2 2.252(2) . ?
Cu1 Cl1 2.272(2) . ?
N1 C3 1.275(10) . ?
N1 C1 1.388(11) . ?
N3 C15 1.363(9) . ?
N3 C13 1.379(10) . ?
N3 C12 1.457(10) . ?
N4 C15 1.327(9) . ?
N4 C14 1.393(10) . ?
N4 Cu1 1.963(6) 3_575 ?
N2 C3 1.343(11) . ?
N2 C2 1.352(12) . ?
N2 C5 1.462(11) . ?
C15 C16 1.478(11) . ?
C14 C13 1.351(11) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C1 C2 1.318(13) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C4 C3 1.474(13) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C9 C10 1.363(12) . ?
C9 C8 1.365(12) . ?
C9 C12 1.518(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C11 1.329(13) . ?
C6 C7 1.360(12) . ?
C6 C5 1.519(12) . ?
C7 C8 1.393(13) . ?
C7 H7 0.9300 . ?
C10 C11 1.401(14) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C13 H13 0.9300 . ?
C3A O1A 1.367(2) . ?
C3A C4A 1.542(2) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
O1A C2A 1.366(2) 3_575 ?
O1A C2A 1.366(2) . ?
O1A C3A 1.367(2) 3_575 ?
C2A C1A 1.542(2) . ?
C2A H2A1 0.9700 . ?
C4A H4A1 0.9600 . ?
C4A H4A2 0.9600 . ?
C4A H4A3 0.9600 . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 0.9600 . ?

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 144.5(3) 3_575 . ?
N4 Cu1 Cl2 95.35(19) 3_575 . ?
N1 Cu1 Cl2 96.9(2) . . ?
N4 Cu1 Cl1 98.9(2) 3_575 . ?
N1 Cu1 Cl1 99.9(2) . . ?
Cl2 Cu1 Cl1 127.08(10) . . ?
C3 N1 C1 106.3(8) . . ?
C3 N1 Cu1 129.5(7) . . ?
C1 N1 Cu1 124.1(7) . . ?
C15 N3 C13 107.4(7) . . ?
C15 N3 C12 127.0(7) . . ?
C13 N3 C12 125.5(7) . . ?
C15 N4 C14 106.0(6) . . ?
C15 N4 Cu1 127.5(5) . 3_575 ?
C14 N4 Cu1 126.3(5) . 3_575 ?
C3 N2 C2 105.9(8) . . ?
C3 N2 C5 130.0(9) . . ?
C2 N2 C5 123.8(9) . . ?
N4 C15 N3 110.5(7) . . ?
N4 C15 C16 126.7(7) . . ?
N3 C15 C16 122.8(8) . . ?
C13 C14 N4 109.5(7) . . ?
C13 C14 H14 125.3 . . ?
N4 C14 H14 125.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C1 N1 107.9(10) . . ?
C2 C1 H1 126.1 . . ?
N1 C1 H1 126.1 . . ?
C1 C2 N2 108.1(9) . . ?
C1 C2 H2 125.9 . . ?
N2 C2 H2 125.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C9 C8 118.8(8) . . ?
C10 C9 C12 122.6(8) . . ?
C8 C9 C12 118.4(8) . . ?
N3 C12 C9 113.2(7) . . ?
N3 C12 H12A 108.9 . . ?
C9 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C9 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C11 C6 C7 118.0(9) . . ?
C11 C6 C5 120.9(9) . . ?
C7 C6 C5 121.0(9) . . ?
C6 C7 C8 121.9(9) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C10 C11 120.0(10) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 121.8(10) . . ?
C6 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C9 C8 C7 119.4(9) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N2 C5 C6 114.1(7) . . ?
N2 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
N2 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N1 C3 N2 111.7(8) . . ?
N1 C3 C4 127.4(9) . . ?
N2 C3 C4 120.8(9) . . ?
C14 C13 N3 106.6(7) . . ?
C14 C13 H13 126.7 . . ?
N3 C13 H13 126.7 . . ?
O1A C3A C4A 115(4) . . ?
O1A C3A H3A1 108.4 . . ?
C4A C3A H3A1 108.4 . . ?
O1A C3A H3A2 108.4 . . ?
C4A C3A H3A2 108.4 . . ?
H3A1 C3A H3A2 107.5 . . ?
C2A O1A C2A 179.998(5) 3_575 . ?
C2A O1A C3A 56.4(3) 3_575 . ?
C2A O1A C3A 123.6(3) . . ?
C2A O1A C3A 123.6(3) 3_575 3_575 ?
C2A O1A C3A 56.4(3) . 3_575 ?
C3A O1A C3A 179.999(8) . 3_575 ?
O1A C2A C1A 110(4) . . ?
O1A C2A H2A1 109.6 . . ?
C1A C2A H2A1 109.6 . . ?
O1A C2A H2A2 109.6 . . ?
C1A C2A H2A2 109.6 . . ?
H2A1 C2A H2A2 108.1 . . ?
C3A C4A H4A1 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?

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
N4 Cu1 N1 C3 68.5(10) 3_575 . . . ?
Cl2 Cu1 N1 C3 177.8(8) . . . . ?
Cl1 Cu1 N1 C3 -52.6(8) . . . . ?
N4 Cu1 N1 C1 -109.7(8) 3_575 . . . ?
Cl2 Cu1 N1 C1 -0.4(8) . . . . ?
Cl1 Cu1 N1 C1 129.2(7) . . . . ?
C14 N4 C15 N3 1.3(9) . . . . ?
Cu1 N4 C15 N3 176.2(5) 3_575 . . . ?
C14 N4 C15 C16 -178.9(8) . . . . ?
Cu1 N4 C15 C16 -4.0(13) 3_575 . . . ?
C13 N3 C15 N4 -1.9(9) . . . . ?
C12 N3 C15 N4 -179.9(7) . . . . ?
C13 N3 C15 C16 178.2(8) . . . . ?
C12 N3 C15 C16 0.3(13) . . . . ?
C15 N4 C14 C13 -0.1(9) . . . . ?
Cu1 N4 C14 C13 -175.1(6) 3_575 . . . ?
C3 N1 C1 C2 0.2(12) . . . . ?
Cu1 N1 C1 C2 178.7(7) . . . . ?
N1 C1 C2 N2 1.1(12) . . . . ?
C3 N2 C2 C1 -1.9(11) . . . . ?
C5 N2 C2 C1 -176.4(8) . . . . ?
C15 N3 C12 C9 -80.6(10) . . . . ?
C13 N3 C12 C9 101.8(9) . . . . ?
C10 C9 C12 N3 -35.0(11) . . . . ?
C8 C9 C12 N3 148.1(8) . . . . ?
C11 C6 C7 C8 -0.2(14) . . . . ?
C5 C6 C7 C8 -179.4(9) . . . . ?
C8 C9 C10 C11 1.1(14) . . . . ?
C12 C9 C10 C11 -175.8(8) . . . . ?
C7 C6 C11 C10 0.9(15) . . . . ?
C5 C6 C11 C10 -179.9(9) . . . . ?
C9 C10 C11 C6 -1.4(16) . . . . ?
C10 C9 C8 C7 -0.4(14) . . . . ?
C12 C9 C8 C7 176.7(8) . . . . ?
C6 C7 C8 C9 -0.1(15) . . . . ?
C3 N2 C5 C6 -82.6(12) . . . . ?
C2 N2 C5 C6 90.5(11) . . . . ?
C11 C6 C5 N2 108.6(11) . . . . ?
C7 C6 C5 N2 -72.2(12) . . . . ?
C1 N1 C3 N2 -1.4(11) . . . . ?
Cu1 N1 C3 N2 -179.9(6) . . . . ?
C1 N1 C3 C4 -179.1(11) . . . . ?
Cu1 N1 C3 C4 2.5(15) . . . . ?
C2 N2 C3 N1 2.1(10) . . . . ?
C5 N2 C3 N1 176.1(8) . . . . ?
C2 N2 C3 C4 179.9(10) . . . . ?
C5 N2 C3 C4 -6.0(15) . . . . ?
N4 C14 C13 N3 -1.1(10) . . . . ?
C15 N3 C13 C14 1.8(9) . . . . ?
C12 N3 C13 C14 179.8(8) . . . . ?
C4A C3A O1A C2A 9(6) . . . 3_575 ?
C4A C3A O1A C2A -171(6) . . . . ?
C3A O1A C2A C1A 169(6) . . . . ?
C3A O1A C2A C1A -11(6) 3_575 . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.102
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.010 0.000 0.000 248 57 ' '
2 -0.025 0.500 0.500 248 57 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1818829'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            4
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H52 Cl4 Cu2 N8 O2'
_chemical_formula_sum            'C40 H52 Cl4 Cu2 N8 O2'
_chemical_formula_weight         945.77

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

_space_group_crystal_system      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                   8.8606(14)
_cell_length_b                   13.145(2)
_cell_length_c                   18.080(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.808(2)
_cell_angle_gamma                90
_cell_volume                     2095.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5527
_cell_measurement_theta_min      2.2645
_cell_measurement_theta_max      25.380

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.186
_exptl_absorpt_coefficient_mu    1.316
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.792
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6772
_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_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30496
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.919
_diffrn_reflns_theta_max         28.301
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5205
_reflns_number_gt                3754
_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    'SHELXS-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)+(0.0213P)²+4.8332P] 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         5205
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.28454(4) 0.69866(3) 0.10374(2) 0.01827(10) Uani 1 1 d . . . . .
Cl2 Cl 0.17502(8) 0.61469(6) 0.19783(4) 0.02001(16) Uani 1 1 d . . . . .
Cl1 Cl 0.49637(9) 0.65461(7) 0.04857(5) 0.02721(18) Uani 1 1 d . . . . .
N1 N 0.3864(3) 0.8029(2) 0.16880(14) 0.0185(5) Uani 1 1 d . . . . .
O1A O 0.1830(3) 0.88073(18) 0.02964(13) 0.0290(5) Uani 1 1 d . . . . .
N3 N 0.0653(3) 1.38284(18) 0.05166(14) 0.0177(5) Uani 1 1 d . . . . .
N4 N -0.1428(3) 1.35522(19) -0.02280(14) 0.0188(5) Uani 1 1 d . . . . .
N2 N 0.4233(3) 0.93999(19) 0.23800(14) 0.0195(5) Uani 1 1 d . . . . .
C8 C 0.1587(3) 1.2419(2) 0.17496(18) 0.0209(6) Uani 1 1 d . . . . .
H8 H 0.058859 1.268753 0.173285 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3454(3) 1.1205(2) 0.22584(17) 0.0195(6) Uani 1 1 d . . . . .
C12 C 0.2241(3) 1.3790(2) 0.08392(17) 0.0192(6) Uani 1 1 d . . . . .
H12A H 0.246181 1.440271 0.114957 0.023 Uiso 1 1 calc R U . . .
H12B H 0.290771 1.380697 0.043187 0.023 Uiso 1 1 calc R U . . .
C9 C 0.2614(3) 1.2853(2) 0.13101(17) 0.0186(6) Uani 1 1 d . . . . .
C14 C 0.0061(3) 1.3371(2) -0.01179(17) 0.0185(6) Uani 1 1 d . . . . .
C13 C -0.1779(4) 1.4160(2) 0.03601(17) 0.0195(6) Uani 1 1 d . . . . .
H13 H -0.275957 1.441080 0.043010 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0965(4) 1.2756(3) -0.06066(18) 0.0242(7) Uani 1 1 d . . . . .
H15A H 0.041349 1.213022 -0.075352 0.036 Uiso 1 1 calc R U . . .
H15B H 0.194629 1.258389 -0.033666 0.036 Uiso 1 1 calc R U . . .
H15C H 0.112856 1.315105 -0.105135 0.036 Uiso 1 1 calc R U . . .
C2 C 0.5630(4) 0.9121(2) 0.21649(18) 0.0223(7) Uani 1 1 d . . . . .
H2 H 0.657073 0.945621 0.229035 0.027 Uiso 1 1 calc R U . . .
C16 C -0.0502(4) 1.4336(2) 0.08162(18) 0.0208(6) Uani 1 1 d . . . . .
H16 H -0.041715 1.473267 0.125770 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1547(3) 0.8788(3) 0.21759(19) 0.0240(7) Uani 1 1 d . . . . .
H4A H 0.109714 0.935342 0.187684 0.036 Uiso 1 1 calc R U . . .
H4B H 0.141324 0.890417 0.270061 0.036 Uiso 1 1 calc R U . . .
H4C H 0.104614 0.815092 0.201045 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3195(3) 0.8719(2) 0.20842(17) 0.0190(6) Uani 1 1 d . . . . .
C10 C 0.4077(3) 1.2435(2) 0.13379(18) 0.0214(6) Uani 1 1 d . . . . .
H10 H 0.478897 1.270430 0.103062 0.026 Uiso 1 1 calc R U . . .
C7 C 0.1992(4) 1.1598(2) 0.22131(18) 0.0220(7) Uani 1 1 d . . . . .
H7 H 0.126415 1.130459 0.250060 0.026 Uiso 1 1 calc R U . . .
C1 C 0.5395(3) 0.8278(2) 0.17416(17) 0.0200(6) Uani 1 1 d . . . . .
H1 H 0.615410 0.791345 0.151678 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3929(4) 1.0335(2) 0.27823(17) 0.0224(7) Uani 1 1 d . . . . .
H5A H 0.485287 1.053362 0.310373 0.027 Uiso 1 1 calc R U . . .
H5B H 0.311431 1.020382 0.310669 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4487(4) 1.1629(2) 0.18140(17) 0.0212(7) Uani 1 1 d . . . . .
H11 H 0.548737 1.136292 0.183696 0.025 Uiso 1 1 calc R U . . .
C4A C 0.2731(4) 0.9723(3) 0.0408(2) 0.0282(7) Uani 1 1 d . . . . .
H4A1 H 0.369113 0.958005 0.072051 0.034 Uiso 1 1 calc R U . . .
H4A2 H 0.216653 1.025302 0.065532 0.034 Uiso 1 1 calc R U . . .
C3A C 0.3050(4) 1.0071(3) -0.0361(2) 0.0309(8) Uani 1 1 d . . . . .
H3A1 H 0.319001 1.081730 -0.037860 0.037 Uiso 1 1 calc R U . . .
H3A2 H 0.395927 0.973067 -0.052060 0.037 Uiso 1 1 calc R U . . .
C2A C 0.1622(4) 0.9742(3) -0.0832(2) 0.0317(8) Uani 1 1 d . . . . .
H2A1 H 0.179654 0.967226 -0.136222 0.038 Uiso 1 1 calc R U . . .
H2A2 H 0.077617 1.022313 -0.078784 0.038 Uiso 1 1 calc R U . . .
C1A C 0.1323(5) 0.8719(3) -0.04870(19) 0.0331(8) Uani 1 1 d . . . . .
H1A1 H 0.022710 0.855506 -0.055868 0.040 Uiso 1 1 calc R U . . .
H1A2 H 0.188940 0.817539 -0.071768 0.040 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 1.962(3) 3_575 ?
Cu1 N1 1.965(3) . ?
Cu1 Cl1 2.2873(9) . ?
Cu1 Cl2 2.3213(9) . ?
N1 C3 1.332(4) . ?
N1 C1 1.389(4) . ?
O1A C1A 1.447(4) . ?
O1A C4A 1.448(4) . ?
N3 C14 1.353(4) . ?
N3 C16 1.378(4) . ?
N3 C12 1.468(4) . ?
N4 C14 1.336(4) . ?
N4 C13 1.390(4) . ?
N2 C3 1.354(4) . ?
N2 C2 1.384(4) . ?
N2 C5 1.467(4) . ?
C8 C9 1.390(4) . ?
C8 C7 1.390(4) . ?
C8 H8 0.9500 . ?
C6 C7 1.390(4) . ?
C6 C11 1.394(4) . ?
C6 C5 1.517(4) . ?
C12 C9 1.515(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 C10 1.404(4) . ?
C14 C15 1.489(4) . ?
C13 C16 1.351(4) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C2 C1 1.351(4) . ?
C2 H2 0.9500 . ?
C16 H16 0.9500 . ?
C4 C3 1.489(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9500 . ?
C7 H7 0.9500 . ?
C1 H1 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 H11 0.9500 . ?
C4A C3A 1.516(5) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C3A C2A 1.516(5) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C2A C1A 1.517(5) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?

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 156.78(10) 3_575 . ?
N4 Cu1 Cl1 94.30(8) 3_575 . ?
N1 Cu1 Cl1 95.16(8) . . ?
N4 Cu1 Cl2 95.25(8) 3_575 . ?
N1 Cu1 Cl2 95.37(8) . . ?
Cl1 Cu1 Cl2 128.43(3) . . ?
C3 N1 C1 106.7(3) . . ?
C3 N1 Cu1 126.5(2) . . ?
C1 N1 Cu1 126.3(2) . . ?
C1A O1A C4A 108.4(2) . . ?
C14 N3 C16 108.0(3) . . ?
C14 N3 C12 126.5(3) . . ?
C16 N3 C12 125.5(3) . . ?
C14 N4 C13 106.4(3) . . ?
C14 N4 Cu1 126.5(2) . 3_575 ?
C13 N4 Cu1 127.0(2) . 3_575 ?
C3 N2 C2 107.7(3) . . ?
C3 N2 C5 126.7(3) . . ?
C2 N2 C5 125.2(3) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C7 C6 C11 118.7(3) . . ?
C7 C6 C5 121.0(3) . . ?
C11 C6 C5 120.3(3) . . ?
N3 C12 C9 113.4(2) . . ?
N3 C12 H12A 108.9 . . ?
C9 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C9 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C8 C9 C10 118.4(3) . . ?
C8 C9 C12 122.4(3) . . ?
C10 C9 C12 119.1(3) . . ?
N4 C14 N3 109.8(3) . . ?
N4 C14 C15 126.2(3) . . ?
N3 C14 C15 124.0(3) . . ?
C16 C13 N4 109.1(3) . . ?
C16 C13 H13 125.4 . . ?
N4 C13 H13 125.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C2 N2 106.6(3) . . ?
C1 C2 H2 126.7 . . ?
N2 C2 H2 126.7 . . ?
C13 C16 N3 106.6(3) . . ?
C13 C16 H16 126.7 . . ?
N3 C16 H16 126.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C3 N2 110.0(3) . . ?
N1 C3 C4 126.6(3) . . ?
N2 C3 C4 123.4(3) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C2 C1 N1 109.1(3) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
N2 C5 C6 112.0(3) . . ?
N2 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C10 C11 C6 121.1(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
O1A C4A C3A 105.9(3) . . ?
O1A C4A H4A1 110.6 . . ?
C3A C4A H4A1 110.6 . . ?
O1A C4A H4A2 110.6 . . ?
C3A C4A H4A2 110.6 . . ?
H4A1 C4A H4A2 108.7 . . ?
C2A C3A C4A 102.0(3) . . ?
C2A C3A H3A1 111.4 . . ?
C4A C3A H3A1 111.4 . . ?
C2A C3A H3A2 111.4 . . ?
C4A C3A H3A2 111.4 . . ?
H3A1 C3A H3A2 109.2 . . ?
C3A C2A C1A 101.1(3) . . ?
C3A C2A H2A1 111.6 . . ?
C1A C2A H2A1 111.6 . . ?
C3A C2A H2A2 111.6 . . ?
C1A C2A H2A2 111.6 . . ?
H2A1 C2A H2A2 109.4 . . ?
O1A C1A C2A 106.4(3) . . ?
O1A C1A H1A1 110.4 . . ?
C2A C1A H1A1 110.4 . . ?
O1A C1A H1A2 110.4 . . ?
C2A C1A H1A2 110.4 . . ?
H1A1 C1A H1A2 108.6 . . ?

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
C14 N3 C12 C9 -83.9(4) . . . . ?
C16 N3 C12 C9 95.4(3) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C7 C8 C9 C12 -175.8(3) . . . . ?
N3 C12 C9 C8 -35.7(4) . . . . ?
N3 C12 C9 C10 147.8(3) . . . . ?
C13 N4 C14 N3 0.6(3) . . . . ?
Cu1 N4 C14 N3 -176.87(19) 3_575 . . . ?
C13 N4 C14 C15 -179.6(3) . . . . ?
Cu1 N4 C14 C15 2.8(4) 3_575 . . . ?
C16 N3 C14 N4 -1.0(3) . . . . ?
C12 N3 C14 N4 178.5(3) . . . . ?
C16 N3 C14 C15 179.3(3) . . . . ?
C12 N3 C14 C15 -1.3(5) . . . . ?
C14 N4 C13 C16 0.0(3) . . . . ?
Cu1 N4 C13 C16 177.5(2) 3_575 . . . ?
C3 N2 C2 C1 0.2(3) . . . . ?
C5 N2 C2 C1 -173.3(3) . . . . ?
N4 C13 C16 N3 -0.6(3) . . . . ?
C14 N3 C16 C13 1.0(3) . . . . ?
C12 N3 C16 C13 -178.5(3) . . . . ?
C1 N1 C3 N2 0.6(3) . . . . ?
Cu1 N1 C3 N2 -171.25(19) . . . . ?
C1 N1 C3 C4 178.1(3) . . . . ?
Cu1 N1 C3 C4 6.3(4) . . . . ?
C2 N2 C3 N1 -0.5(3) . . . . ?
C5 N2 C3 N1 172.9(3) . . . . ?
C2 N2 C3 C4 -178.1(3) . . . . ?
C5 N2 C3 C4 -4.7(5) . . . . ?
C8 C9 C10 C11 -2.1(5) . . . . ?
C12 C9 C10 C11 174.5(3) . . . . ?
C11 C6 C7 C8 -1.9(5) . . . . ?
C5 C6 C7 C8 177.8(3) . . . . ?
C9 C8 C7 C6 1.3(5) . . . . ?
N2 C2 C1 N1 0.2(3) . . . . ?
C3 N1 C1 C2 -0.5(3) . . . . ?
Cu1 N1 C1 C2 171.4(2) . . . . ?
C3 N2 C5 C6 -81.7(4) . . . . ?
C2 N2 C5 C6 90.6(4) . . . . ?
C7 C6 C5 N2 112.7(3) . . . . ?
C11 C6 C5 N2 -67.7(4) . . . . ?
C9 C10 C11 C6 1.5(5) . . . . ?
C7 C6 C11 C10 0.5(5) . . . . ?
C5 C6 C11 C10 -179.1(3) . . . . ?
C1A O1A C4A C3A -12.4(4) . . . . ?
O1A C4A C3A C2A 32.9(4) . . . . ?
C4A C3A C2A C1A -39.5(4) . . . . ?
C4A O1A C1A C2A -13.3(4) . . . . ?
C3A C2A C1A O1A 33.3(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
C12 H12A Cl2 0.99 2.84 3.770(3) 155.9 1_565
C12 H12B Cl1 0.99 2.68 3.643(3) 165.6 3_675
C13 H13 Cl1 0.95 2.74 3.208(3) 111.5 3_575
C15 H15A O1A 0.98 2.55 3.310(4) 134.6 3_575
C2 H2 Cl2 0.95 2.92 3.762(3) 149.0 2_655
C16 H16 Cl2 0.95 2.89 3.635(3) 136.5 1_565
C4 H4C Cl2 0.98 2.71 3.496(3) 137.6 .
C1 H1 Cl1 0.95 2.72 3.210(3) 112.5 .
C5 H5A Cl1 0.99 2.87 3.561(3) 127.8 2_655
C4A H4A1 N1 0.99 2.68 3.294(4) 120.4 .

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.091



####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1819551'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H36 Cl4 Cu2 N8, 2(C3 H6 O)'
_chemical_formula_sum            'C38 H48 Cl4 Cu2 N8 O2'
_chemical_formula_weight         917.72

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

_space_group_crystal_system      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                   8.7550(7)
_cell_length_b                   13.3722(11)
_cell_length_c                   17.6870(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.982(3)
_cell_angle_gamma                90
_cell_volume                     2059.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2566
_cell_measurement_theta_min      2.772
_cell_measurement_theta_max      24.113

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    1.336
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9967
_exptl_absorpt_correction_T_max  0.9997
_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  graphite
_diffrn_measurement_method       'Bruker APEX CCD area -detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25262
_diffrn_reflns_av_unetI/netI     0.1874
_diffrn_reflns_av_R_equivalents  0.2815
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.913
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5117
_reflns_number_gt                2759
_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.
The authors acknowledge the presence of two A alerts regarding the Rint
being greater than 0.25. This is due to the crystal having undergone
two SC-SC transformations. Since this structure was previously reported
this data is considered sufficient.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-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)+(0.0011P)²+16.7965P] 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         5117
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1878
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.2149
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
Cu01 Cu -0.19954(10) 0.69383(7) 0.10050(5) 0.0206(2) Uani 1 1 d . . . . .
Cl02 Cl -0.3168(2) 0.62346(13) 0.19678(10) 0.0224(4) Uani 1 1 d . . . . .
Cl03 Cl 0.0150(2) 0.64883(14) 0.04815(10) 0.0268(4) Uani 1 1 d . . . . .
N4 N -0.6583(6) 1.3591(4) -0.0163(3) 0.0199(13) Uani 1 1 d . . . . .
N3 N -0.4482(7) 1.3900(4) 0.0585(3) 0.0216(13) Uani 1 1 d . . . . .
N1 N -0.1109(7) 0.8124(4) 0.1552(3) 0.0214(13) Uani 1 1 d . . . . .
N2 N -0.0769(7) 0.9470(4) 0.2262(3) 0.0204(13) Uani 1 1 d . . . . .
C8 C -0.0946(9) 1.2609(5) 0.1451(4) 0.0242(16) Uani 1 1 d . . . . .
H8 H -0.020211 1.296028 0.119967 0.029 Uiso 1 1 calc R U . . .
C9 C -0.2474(8) 1.2933(5) 0.1372(4) 0.0203(15) Uani 1 1 d . . . . .
C3 C -0.1803(8) 0.8781(5) 0.1972(4) 0.0209(15) Uani 1 1 d . . . . .
C6 C -0.1569(8) 1.1242(5) 0.2262(4) 0.0186(15) Uani 1 1 d . . . . .
C15 C -0.5075(8) 1.3393(5) -0.0037(4) 0.0205(15) Uani 1 1 d . . . . .
C1 C 0.0411(8) 0.8424(6) 0.1575(4) 0.0223(16) Uani 1 1 d . . . . .
H1 H 0.117855 0.809872 0.132237 0.027 Uiso 1 1 calc R U . . .
C12 C -0.2876(8) 1.3875(5) 0.0923(4) 0.0205(15) Uani 1 1 d . . . . .
H12A H -0.268250 1.446071 0.126191 0.025 Uiso 1 1 calc R U . . .
H12B H -0.219438 1.393280 0.051204 0.025 Uiso 1 1 calc R U . . .
C7 C -0.0503(8) 1.1775(5) 0.1895(4) 0.0226(16) Uani 1 1 d . . . . .
H7 H 0.054157 1.156982 0.194637 0.027 Uiso 1 1 calc R U . . .
C10 C -0.3524(9) 1.2406(5) 0.1755(4) 0.0228(16) Uani 1 1 d . . . . .
H10 H -0.456132 1.262438 0.171851 0.027 Uiso 1 1 calc R U . . .
C14 C -0.6945(8) 1.4245(5) 0.0397(4) 0.0218(16) Uani 1 1 d . . . . .
H14 H -0.793771 1.450844 0.044649 0.026 Uiso 1 1 calc R U . . .
C2 C 0.0627(9) 0.9245(6) 0.2009(4) 0.0257(17) Uani 1 1 d . . . . .
H2 H 0.156167 0.960105 0.212100 0.031 Uiso 1 1 calc R U . . .
C13 C -0.5634(8) 1.4454(5) 0.0871(4) 0.0224(16) Uani 1 1 d . . . . .
H13 H -0.553931 1.488372 0.130117 0.027 Uiso 1 1 calc R U . . .
C11 C -0.3094(9) 1.1572(6) 0.2186(4) 0.0236(16) Uani 1 1 d . . . . .
H11 H -0.384068 1.121955 0.243459 0.028 Uiso 1 1 calc R U . . .
C4 C -0.3436(8) 0.8803(6) 0.2101(5) 0.0301(18) Uani 1 1 d . . . . .
H4A H -0.392281 0.817021 0.193110 0.045 Uiso 1 1 calc R U . . .
H4B H -0.394793 0.935709 0.181442 0.045 Uiso 1 1 calc R U . . .
H4C H -0.352590 0.889499 0.264456 0.045 Uiso 1 1 calc R U . . .
C16 C -0.4189(9) 1.2716(6) -0.0483(4) 0.0277(17) Uani 1 1 d . . . . .
H16A H -0.458889 1.203371 -0.045530 0.041 Uiso 1 1 calc R U . . .
H16B H -0.310554 1.272733 -0.027678 0.041 Uiso 1 1 calc R U . . .
H16C H -0.428190 1.293573 -0.101457 0.041 Uiso 1 1 calc R U . . .
C5 C -0.1078(9) 1.0337(6) 0.2730(4) 0.0256(17) Uani 1 1 d . . . . .
H5A H -0.014015 1.050087 0.306896 0.031 Uiso 1 1 calc R U . . .
H5B H -0.189582 1.016183 0.305345 0.031 Uiso 1 1 calc R U . . .
C3A C -0.7909(12) 0.9666(8) -0.0256(5) 0.053(3) Uani 1 1 d . . . . .
H3A1 H -0.720943 0.939569 -0.060260 0.080 Uiso 1 1 calc R U . . .
H3A2 H -0.857984 1.016775 -0.052232 0.080 Uiso 1 1 calc R U . . .
H3A3 H -0.853567 0.912277 -0.007958 0.080 Uiso 1 1 calc R U . . .
C2A C -0.6990(13) 1.0143(8) 0.0417(7) 0.063(3) Uani 1 1 d . . . . .
C1A C -0.7340(12) 1.1126(7) 0.0623(6) 0.057(3) Uani 1 1 d . . . . .
H1A1 H -0.844399 1.118151 0.066462 0.086 Uiso 1 1 calc R U . . .
H1A2 H -0.705077 1.159170 0.023443 0.086 Uiso 1 1 calc R U . . .
H1A3 H -0.676809 1.128969 0.111341 0.086 Uiso 1 1 calc R U . . .
O1A O -0.645(2) 0.9586(11) 0.0972(8) 0.074(5) Uani 0.55 1 d . . P A 1
O2A O -0.5508(18) 0.9854(13) 0.0536(11) 0.061(5) Uani 0.45 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
Cu01 N4 1.970(6) 3_475 ?
Cu01 N1 1.974(6) . ?
Cu01 Cl03 2.261(2) . ?
Cu01 Cl02 2.2811(19) . ?
N4 C15 1.343(9) . ?
N4 C14 1.383(9) . ?
N3 C15 1.349(9) . ?
N3 C13 1.389(9) . ?
N3 C12 1.470(9) . ?
N1 C3 1.336(9) . ?
N1 C1 1.386(9) . ?
N2 C3 1.355(9) . ?
N2 C2 1.378(9) . ?
N2 C5 1.465(9) . ?
C8 C7 1.395(10) . ?
C8 C9 1.399(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(10) . ?
C9 C12 1.511(10) . ?
C3 C4 1.472(10) . ?
C6 C7 1.388(10) . ?
C6 C11 1.399(10) . ?
C6 C5 1.503(10) . ?
C15 C16 1.474(10) . ?
C1 C2 1.342(10) . ?
C1 H1 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C7 H7 0.9500 . ?
C10 C11 1.382(10) . ?
C10 H10 0.9500 . ?
C14 C13 1.378(10) . ?
C14 H14 0.9500 . ?
C2 H2 0.9500 . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3A C2A 1.507(14) . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
C2A O1A 1.284(17) . ?
C2A O2A 1.349(18) . ?
C2A C1A 1.406(14) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?

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 Cu01 N1 147.6(2) 3_475 . ?
N4 Cu01 Cl03 94.66(17) 3_475 . ?
N1 Cu01 Cl03 96.52(18) . . ?
N4 Cu01 Cl02 96.77(17) 3_475 . ?
N1 Cu01 Cl02 98.62(18) . . ?
Cl03 Cu01 Cl02 130.82(8) . . ?
C15 N4 C14 107.5(6) . . ?
C15 N4 Cu01 126.0(5) . 3_475 ?
C14 N4 Cu01 126.5(5) . 3_475 ?
C15 N3 C13 109.5(6) . . ?
C15 N3 C12 126.2(6) . . ?
C13 N3 C12 124.4(6) . . ?
C3 N1 C1 106.6(6) . . ?
C3 N1 Cu01 128.4(5) . . ?
C1 N1 Cu01 125.0(5) . . ?
C3 N2 C2 107.9(6) . . ?
C3 N2 C5 126.6(6) . . ?
C2 N2 C5 125.4(6) . . ?
C7 C8 C9 120.7(7) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 117.9(7) . . ?
C10 C9 C12 123.3(6) . . ?
C8 C9 C12 118.6(6) . . ?
N1 C3 N2 109.4(6) . . ?
N1 C3 C4 127.2(6) . . ?
N2 C3 C4 123.3(6) . . ?
C7 C6 C11 118.3(6) . . ?
C7 C6 C5 120.2(6) . . ?
C11 C6 C5 121.4(7) . . ?
N4 C15 N3 108.9(6) . . ?
N4 C15 C16 126.6(6) . . ?
N3 C15 C16 124.5(6) . . ?
C2 C1 N1 109.3(6) . . ?
C2 C1 H1 125.4 . . ?
N1 C1 H1 125.4 . . ?
N3 C12 C9 113.1(6) . . ?
N3 C12 H12A 109.0 . . ?
C9 C12 H12A 109.0 . . ?
N3 C12 H12B 109.0 . . ?
C9 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C6 C7 C8 120.8(7) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C11 C10 C9 121.5(7) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C13 C14 N4 109.0(6) . . ?
C13 C14 H14 125.5 . . ?
N4 C14 H14 125.5 . . ?
C1 C2 N2 106.8(6) . . ?
C1 C2 H2 126.6 . . ?
N2 C2 H2 126.6 . . ?
C14 C13 N3 105.1(6) . . ?
C14 C13 H13 127.4 . . ?
N3 C13 H13 127.4 . . ?
C10 C11 C6 120.6(7) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C5 C6 112.6(5) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C2A C3A H3A1 109.5 . . ?
C2A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C2A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
O1A C2A C1A 114.7(11) . . ?
O2A C2A C1A 117.3(12) . . ?
O1A C2A C3A 118.8(11) . . ?
O2A C2A C3A 115.3(11) . . ?
C1A C2A C3A 119.2(10) . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?

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
C7 C8 C9 C10 0.7(11) . . . . ?
C7 C8 C9 C12 176.4(6) . . . . ?
C1 N1 C3 N2 -0.7(8) . . . . ?
Cu01 N1 C3 N2 178.5(4) . . . . ?
C1 N1 C3 C4 177.8(7) . . . . ?
Cu01 N1 C3 C4 -3.0(11) . . . . ?
C2 N2 C3 N1 0.6(8) . . . . ?
C5 N2 C3 N1 177.7(6) . . . . ?
C2 N2 C3 C4 -178.0(7) . . . . ?
C5 N2 C3 C4 -0.9(11) . . . . ?
C14 N4 C15 N3 0.1(8) . . . . ?
Cu01 N4 C15 N3 179.2(4) 3_475 . . . ?
C14 N4 C15 C16 178.7(7) . . . . ?
Cu01 N4 C15 C16 -2.2(11) 3_475 . . . ?
C13 N3 C15 N4 -0.5(8) . . . . ?
C12 N3 C15 N4 179.0(6) . . . . ?
C13 N3 C15 C16 -179.2(7) . . . . ?
C12 N3 C15 C16 0.4(11) . . . . ?
C3 N1 C1 C2 0.6(8) . . . . ?
Cu01 N1 C1 C2 -178.7(5) . . . . ?
C15 N3 C12 C9 -76.5(8) . . . . ?
C13 N3 C12 C9 103.0(7) . . . . ?
C10 C9 C12 N3 -30.8(9) . . . . ?
C8 C9 C12 N3 153.7(6) . . . . ?
C11 C6 C7 C8 -1.1(10) . . . . ?
C5 C6 C7 C8 179.2(7) . . . . ?
C9 C8 C7 C6 0.6(11) . . . . ?
C8 C9 C10 C11 -1.6(10) . . . . ?
C12 C9 C10 C11 -177.1(6) . . . . ?
C15 N4 C14 C13 0.3(8) . . . . ?
Cu01 N4 C14 C13 -178.8(5) 3_475 . . . ?
N1 C1 C2 N2 -0.2(8) . . . . ?
C3 N2 C2 C1 -0.2(8) . . . . ?
C5 N2 C2 C1 -177.3(6) . . . . ?
N4 C14 C13 N3 -0.6(8) . . . . ?
C15 N3 C13 C14 0.7(8) . . . . ?
C12 N3 C13 C14 -178.9(6) . . . . ?
C9 C10 C11 C6 1.1(11) . . . . ?
C7 C6 C11 C10 0.2(10) . . . . ?
C5 C6 C11 C10 180.0(6) . . . . ?
C3 N2 C5 C6 -87.6(9) . . . . ?
C2 N2 C5 C6 89.0(8) . . . . ?
C7 C6 C5 N2 -73.6(8) . . . . ?
C11 C6 C5 N2 106.6(8) . . . . ?

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
C1 H1 Cl03 0.95 2.72 3.224(8) 114.2 .
C12 H12A Cl02 0.99 2.73 3.679(7) 159.7 1_565
C12 H12B Cl03 0.99 2.70 3.652(7) 162.6 3_575
C14 H14 Cl03 0.95 2.75 3.216(7) 111.1 3_475
C13 H13 Cl02 0.95 2.91 3.636(8) 134.4 1_565
C4 H4A Cl02 0.98 2.67 3.452(8) 136.9 .
C4 H4B O1A 0.98 2.53 3.308(15) 135.7 .
C4 H4B O2A 0.98 2.60 3.45(2) 144.4 .
C16 H16A O1A 0.98 2.55 3.260(16) 128.9 3_475
C16 H16A O2A 0.98 2.53 3.447(19) 155.7 3_475
C16 H16B Cl03 0.98 2.85 3.692(8) 144.5 3_575
C16 H16C Cl02 0.98 2.88 3.599(8) 131.3 3_475
C5 H5A Cl03 0.99 2.88 3.536(7) 124.1 2
C3A H3A1 O2A 0.98 2.57 3.15(2) 117.6 3_475

_refine_diff_density_max         0.744
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.164



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1819550'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            2
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H36 Cl4 Cu2 N8, 2(C2 H3 N)'
_chemical_formula_sum            'C36 H42 Cl4 Cu2 N10'
_chemical_formula_weight         883.67

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                   8.5707(12)
_cell_length_b                   12.8298(16)
_cell_length_c                   18.181(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.579(4)
_cell_angle_gamma                90
_cell_volume                     1998.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3644
_cell_measurement_theta_min      2.377
_cell_measurement_theta_max      24.61

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    1.372
_shelx_estimated_absorpt_T_min   0.783
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5463
_exptl_absorpt_correction_T_max  0.6615
_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  graphite
_diffrn_measurement_method       'Bruker APEX CCD area -detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23174
_diffrn_reflns_av_unetI/netI     0.1393
_diffrn_reflns_av_R_equivalents  0.1386
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.943
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4970
_reflns_number_gt                2659
_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    'SHELXS-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)+(0.0501P)²+9.5867P] 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         4970
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1688
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1857
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Cu01 Cu 0.75010(9) 0.69210(6) 0.11662(4) 0.0241(2) Uani 1 1 d . . . . .
Cl1 Cl 0.98357(18) 0.61631(12) 0.09137(8) 0.0262(4) Uani 1 1 d . . . . .
Cl2 Cl 0.57505(19) 0.62976(13) 0.19794(8) 0.0307(4) Uani 1 1 d . . . . .
N4 N 0.3603(6) 1.3437(4) -0.0235(3) 0.0230(11) Uani 1 1 d . . . . .
N1 N 0.8284(6) 0.8052(4) 0.1796(3) 0.0247(11) Uani 1 1 d . . . . .
N2 N 0.9539(6) 0.9460(4) 0.2160(3) 0.0246(12) Uani 1 1 d . . . . .
N3 N 0.5475(6) 1.3783(4) 0.0575(3) 0.0255(12) Uani 1 1 d . . . . .
C15 C 0.5120(7) 1.3298(5) -0.0066(3) 0.0222(13) Uani 1 1 d . . . . .
C3 C 0.9244(7) 0.8821(5) 0.1585(3) 0.0241(14) Uani 1 1 d . . . . .
C14 C 0.2989(7) 1.4009(5) 0.0333(3) 0.0237(14) Uani 1 1 d . . . . .
H14 H 0.192902 1.421469 0.036631 0.028 Uiso 1 1 calc R U . . .
C10 C 0.9153(7) 1.2597(5) 0.0862(3) 0.0252(14) Uani 1 1 d . . . . .
H10 H 0.947059 1.288956 0.041041 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7050(7) 1.3963(5) 0.0892(4) 0.0272(15) Uani 1 1 d . . . . .
H12A H 0.697529 1.449400 0.128438 0.033 Uiso 1 1 calc R U . . .
H12B H 0.770498 1.425913 0.050365 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7884(7) 1.3011(5) 0.1215(3) 0.0247(14) Uani 1 1 d . . . . .
C5 C 1.0456(7) 1.0425(5) 0.2152(3) 0.0257(14) Uani 1 1 d . . . . .
H5A H 1.139955 1.031196 0.186049 0.031 Uiso 1 1 calc R U . . .
H5B H 1.080202 1.059746 0.266189 0.031 Uiso 1 1 calc R U . . .
C4 C 0.9888(9) 0.8944(5) 0.0845(3) 0.0330(16) Uani 1 1 d . . . . .
H4A H 0.963553 0.832710 0.054771 0.049 Uiso 1 1 calc R U . . .
H4B H 1.102438 0.902433 0.088885 0.049 Uiso 1 1 calc R U . . .
H4C H 0.943314 0.956388 0.060823 0.049 Uiso 1 1 calc R U . . .
C6 C 0.9550(7) 1.1330(5) 0.1833(3) 0.0246(14) Uani 1 1 d . . . . .
C1 C 0.7941(8) 0.8243(5) 0.2523(3) 0.0264(14) Uani 1 1 d . . . . .
H1 H 0.727618 0.783012 0.281443 0.032 Uiso 1 1 calc R U . . .
C2 C 0.8711(8) 0.9119(5) 0.2754(4) 0.0274(15) Uani 1 1 d . . . . .
H2 H 0.868276 0.943079 0.322759 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4139(8) 1.4228(5) 0.0832(3) 0.0262(14) Uani 1 1 d . . . . .
H13 H 0.404161 1.461456 0.127378 0.031 Uiso 1 1 calc R U . . .
C11 C 0.9957(7) 1.1764(5) 0.1162(3) 0.0259(14) Uani 1 1 d . . . . .
H11 H 1.080896 1.147786 0.090584 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6248(7) 1.2697(5) -0.0499(4) 0.0316(15) Uani 1 1 d . . . . .
H16A H 0.716495 1.313051 -0.059043 0.047 Uiso 1 1 calc R U . . .
H16B H 0.575646 1.249105 -0.097018 0.047 Uiso 1 1 calc R U . . .
H16C H 0.657125 1.207297 -0.022450 0.047 Uiso 1 1 calc R U . . .
C7 C 0.8300(8) 1.1755(5) 0.2187(3) 0.0282(15) Uani 1 1 d . . . . .
H7 H 0.801237 1.147287 0.264703 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7441(8) 1.2588(5) 0.1889(4) 0.0312(15) Uani 1 1 d . . . . .
H8 H 0.657282 1.286214 0.213892 0.037 Uiso 1 1 calc R U . . .
N1A N 0.3331(10) 1.0640(8) 0.0414(4) 0.075(3) Uani 1 1 d . . . . .
C2A C 0.4323(10) 1.0397(7) 0.0815(5) 0.050(2) Uani 1 1 d . . . . .
C1A C 0.5571(11) 1.0087(8) 0.1299(5) 0.066(3) Uani 1 1 d . . . . .
H1A1 H 0.581255 0.935031 0.121614 0.099 Uiso 1 1 calc R U . . .
H1A2 H 0.526516 1.018582 0.180958 0.099 Uiso 1 1 calc R U . . .
H1A3 H 0.649513 1.051102 0.120410 0.099 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
Cu01 N1 1.956(5) . ?
Cu01 N4 1.971(5) 3_675 ?
Cu01 Cl2 2.2800(18) . ?
Cu01 Cl1 2.2827(17) . ?
N4 C15 1.340(7) . ?
N4 C14 1.381(8) . ?
N1 C3 1.347(8) . ?
N1 C1 1.383(8) . ?
N2 C3 1.346(7) . ?
N2 C2 1.381(8) . ?
N2 C5 1.467(8) . ?
N3 C15 1.350(7) . ?
N3 C13 1.373(8) . ?
N3 C12 1.471(8) . ?
C15 C16 1.480(9) . ?
C3 C4 1.477(9) . ?
C14 C13 1.351(8) . ?
C14 H14 0.9500 . ?
C10 C11 1.377(8) . ?
C10 C9 1.383(9) . ?
C10 H10 0.9500 . ?
C12 C9 1.523(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 C8 1.403(9) . ?
C5 C6 1.505(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.377(9) . ?
C6 C11 1.394(9) . ?
C1 C2 1.363(9) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C7 C8 1.399(9) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N1A C2A 1.147(10) . ?
C2A C1A 1.423(12) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu01 N4 145.6(2) . 3_675 ?
N1 Cu01 Cl2 95.84(16) . . ?
N4 Cu01 Cl2 99.57(16) 3_675 . ?
N1 Cu01 Cl1 98.36(16) . . ?
N4 Cu01 Cl1 97.50(16) 3_675 . ?
Cl2 Cu01 Cl1 125.25(7) . . ?
C15 N4 C14 106.7(5) . . ?
C15 N4 Cu01 127.2(4) . 3_675 ?
C14 N4 Cu01 125.6(4) . 3_675 ?
C3 N1 C1 106.9(5) . . ?
C3 N1 Cu01 125.3(4) . . ?
C1 N1 Cu01 127.7(4) . . ?
C3 N2 C2 109.0(5) . . ?
C3 N2 C5 126.6(5) . . ?
C2 N2 C5 124.2(5) . . ?
C15 N3 C13 108.3(5) . . ?
C15 N3 C12 126.4(5) . . ?
C13 N3 C12 124.5(5) . . ?
N4 C15 N3 109.3(5) . . ?
N4 C15 C16 126.3(5) . . ?
N3 C15 C16 124.4(5) . . ?
N2 C3 N1 109.1(5) . . ?
N2 C3 C4 125.0(6) . . ?
N1 C3 C4 125.8(5) . . ?
C13 C14 N4 109.1(6) . . ?
C13 C14 H14 125.5 . . ?
N4 C14 H14 125.5 . . ?
C11 C10 C9 120.5(6) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
N3 C12 C9 116.2(5) . . ?
N3 C12 H12A 108.2 . . ?
C9 C12 H12A 108.2 . . ?
N3 C12 H12B 108.2 . . ?
C9 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C10 C9 C8 119.4(6) . . ?
C10 C9 C12 119.7(6) . . ?
C8 C9 C12 120.8(6) . . ?
N2 C5 C6 112.6(5) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C6 C11 117.9(6) . . ?
C7 C6 C5 121.6(6) . . ?
C11 C6 C5 120.4(6) . . ?
C2 C1 N1 109.1(6) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C1 C2 N2 105.9(5) . . ?
C1 C2 H2 127.0 . . ?
N2 C2 H2 127.0 . . ?
C14 C13 N3 106.6(5) . . ?
C14 C13 H13 126.7 . . ?
N3 C13 H13 126.7 . . ?
C10 C11 C6 121.4(6) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C7 C8 121.9(6) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C9 118.8(6) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
N1A C2A C1A 178.8(9) . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?

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
C14 N4 C15 N3 -1.5(6) . . . . ?
Cu01 N4 C15 N3 170.7(4) 3_675 . . . ?
C14 N4 C15 C16 177.7(6) . . . . ?
Cu01 N4 C15 C16 -10.0(9) 3_675 . . . ?
C13 N3 C15 N4 1.3(7) . . . . ?
C12 N3 C15 N4 -169.4(5) . . . . ?
C13 N3 C15 C16 -178.0(6) . . . . ?
C12 N3 C15 C16 11.3(10) . . . . ?
C2 N2 C3 N1 -2.0(7) . . . . ?
C5 N2 C3 N1 -176.2(5) . . . . ?
C2 N2 C3 C4 178.6(6) . . . . ?
C5 N2 C3 C4 4.3(10) . . . . ?
C1 N1 C3 N2 1.7(7) . . . . ?
Cu01 N1 C3 N2 180.0(4) . . . . ?
C1 N1 C3 C4 -178.8(6) . . . . ?
Cu01 N1 C3 C4 -0.6(9) . . . . ?
C15 N4 C14 C13 1.2(7) . . . . ?
Cu01 N4 C14 C13 -171.2(4) 3_675 . . . ?
C15 N3 C12 C9 -73.4(8) . . . . ?
C13 N3 C12 C9 117.3(7) . . . . ?
C11 C10 C9 C8 1.2(9) . . . . ?
C11 C10 C9 C12 177.4(5) . . . . ?
N3 C12 C9 C10 109.8(7) . . . . ?
N3 C12 C9 C8 -74.1(8) . . . . ?
C3 N2 C5 C6 78.9(8) . . . . ?
C2 N2 C5 C6 -94.5(7) . . . . ?
N2 C5 C6 C7 67.9(7) . . . . ?
N2 C5 C6 C11 -111.9(6) . . . . ?
C3 N1 C1 C2 -0.8(7) . . . . ?
Cu01 N1 C1 C2 -179.0(4) . . . . ?
N1 C1 C2 N2 -0.3(7) . . . . ?
C3 N2 C2 C1 1.4(7) . . . . ?
C5 N2 C2 C1 175.8(5) . . . . ?
N4 C14 C13 N3 -0.4(7) . . . . ?
C15 N3 C13 C14 -0.5(7) . . . . ?
C12 N3 C13 C14 170.4(5) . . . . ?
C9 C10 C11 C6 -1.6(9) . . . . ?
C7 C6 C11 C10 0.7(9) . . . . ?
C5 C6 C11 C10 -179.5(6) . . . . ?
C11 C6 C7 C8 0.6(9) . . . . ?
C5 C6 C7 C8 -179.2(6) . . . . ?
C6 C7 C8 C9 -0.9(10) . . . . ?
C10 C9 C8 C7 0.0(9) . . . . ?
C12 C9 C8 C7 -176.1(6) . . . . ?

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 H14 Cl1 0.95 2.78 3.278(6) 113.4 3_675
C12 H12A Cl2 0.99 2.85 3.774(7) 155.5 1_565
C5 H5B Cl1 0.99 2.76 3.657(7) 151.1 2_755
C4 H4A Cl1 0.98 2.86 3.571(7) 130.2 .
C1 H1 Cl2 0.95 2.79 3.260(7) 111.7 .
C2 H2 Cl1 0.95 2.98 3.759(7) 140.2 2_755
C13 H13 Cl2 0.95 2.89 3.627(6) 135.3 1_565
C16 H16A Cl1 0.98 2.80 3.756(7) 164.3 3_775
C16 H16B Cl2 0.98 2.71 3.403(7) 128.5 3_675
C1A H1A2 Cl2 0.98 2.78 3.700(9) 156.0 2_655

_refine_diff_density_max         0.778
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.139



####################################################################### 
# 
# 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_5_100K
_database_code_depnum_ccdc_archive 'CCDC 1818830'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            5_100K
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H36 Cl4 Cu2 N8, 0.88(C4 H10 O)'
_chemical_formula_sum            'C35.52 H44.80 Cl4 Cu2 N8 O0.88'
_chemical_formula_weight         866.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.5758(4)
_cell_length_b                   13.2950(6)
_cell_length_c                   17.9793(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.182(2)
_cell_angle_gamma                90
_cell_volume                     2041.54(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    7749
_cell_measurement_theta_min      2.275
_cell_measurement_theta_max      28.136

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             894
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.158
_exptl_absorpt_coefficient_mu    1.342
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.816
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31495
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5076
_reflns_number_gt                3387
_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    'SHELXS-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)+(0.0482P)²+5.2811P] 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         5076
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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 0.30249(6) 0.69599(4) 0.10003(3) 0.02200(15) Uani 1 1 d . . . . .
Cl2 Cl 0.17080(12) 0.62665(8) 0.19246(6) 0.0248(2) Uani 1 1 d . . . . .
Cl1 Cl 0.52411(12) 0.64151(9) 0.05378(6) 0.0289(3) Uani 1 1 d . . . . .
N3 N 0.0506(4) 1.3850(3) 0.05834(19) 0.0218(7) Uani 1 1 d . . . . .
N4 N -0.1621(4) 1.3522(2) -0.01473(18) 0.0200(7) Uani 1 1 d . . . . .
N1 N 0.3975(4) 0.8107(3) 0.15673(19) 0.0238(8) Uani 1 1 d . . . . .
N2 N 0.4359(4) 0.9456(3) 0.22650(19) 0.0241(8) Uani 1 1 d . . . . .
C6 C 0.3529(5) 1.1247(3) 0.2241(2) 0.0234(9) Uani 1 1 d . . . . .
C16 C 0.0812(5) 1.2586(4) -0.0424(2) 0.0284(10) Uani 1 1 d . . . . .
H16A H 0.071700 1.276661 -0.095433 0.043 Uiso 1 1 calc R U . . .
H16B H 0.040925 1.190339 -0.036471 0.043 Uiso 1 1 calc R U . . .
H16C H 0.191496 1.261318 -0.022776 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3282(5) 0.8792(3) 0.1974(2) 0.0254(9) Uani 1 1 d . . . . .
C9 C 0.2577(5) 1.2911(3) 0.1357(2) 0.0217(9) Uani 1 1 d . . . . .
C5 C 0.4062(5) 1.0345(3) 0.2714(2) 0.0277(10) Uani 1 1 d . . . . .
H5A H 0.503177 1.052192 0.302700 0.033 Uiso 1 1 calc R U . . .
H5B H 0.324875 1.017959 0.305160 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2135(5) 1.3847(3) 0.0908(2) 0.0258(9) Uani 1 1 d . . . . .
H12A H 0.231137 1.444247 0.123563 0.031 Uiso 1 1 calc R U . . .
H12B H 0.283299 1.390813 0.050092 0.031 Uiso 1 1 calc R U . . .
C1 C 0.5544(5) 0.8370(3) 0.1602(3) 0.0277(10) Uani 1 1 d . . . . .
H1 H 0.632470 0.802545 0.135858 0.033 Uiso 1 1 calc R U . . .
C2 C 0.5783(5) 0.9188(3) 0.2033(3) 0.0288(10) Uani 1 1 d . . . . .
H2 H 0.675406 0.951964 0.215521 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4587(5) 1.1737(3) 0.1821(2) 0.0268(10) Uani 1 1 d . . . . .
H7 H 0.563881 1.150889 0.183589 0.032 Uiso 1 1 calc R U . . .
C13 C -0.0680(5) 1.4438(3) 0.0829(2) 0.0266(10) Uani 1 1 d . . . . .
H13 H -0.059146 1.490035 0.123326 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4110(5) 1.2557(3) 0.1382(2) 0.0277(10) Uani 1 1 d . . . . .
H8 H 0.483775 1.288159 0.109415 0.033 Uiso 1 1 calc R U . . .
C10 C 0.1533(5) 1.2413(3) 0.1775(3) 0.0287(10) Uani 1 1 d . . . . .
H10 H 0.047914 1.263737 0.176024 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1604(6) 0.8857(4) 0.2093(4) 0.0513(16) Uani 1 1 d . . . . .
H4A H 0.113343 0.943248 0.181641 0.077 Uiso 1 1 calc R U . . .
H4B H 0.149052 0.894307 0.262711 0.077 Uiso 1 1 calc R U . . .
H4C H 0.107295 0.823734 0.191588 0.077 Uiso 1 1 calc R U . . .
C11 C 0.2011(6) 1.1586(4) 0.2215(3) 0.0306(10) Uani 1 1 d . . . . .
H11 H 0.128241 1.125556 0.249968 0.037 Uiso 1 1 calc R U . . .
C14 C -0.1992(5) 1.4222(3) 0.0379(2) 0.0245(9) Uani 1 1 d . . . . .
H14 H -0.299913 1.450475 0.041814 0.029 Uiso 1 1 calc R U . . .
C15 C -0.0111(5) 1.3308(3) -0.0004(2) 0.0233(9) Uani 1 1 d . . . . .
O1A O -0.021(4) 1.009(3) -0.003(2) 0.037(4) Uani 0.440(5) 1 d . . P A -1
C1A C -0.285(3) 1.046(4) 0.017(2) 0.090(11) Uani 0.440(5) 1 d . . P A -1
H1A1 H -0.283530 1.094385 -0.024381 0.135 Uiso 0.440(5) 1 calc R U P A -1
H1A2 H -0.348235 1.073608 0.054941 0.135 Uiso 0.440(5) 1 calc R U P A -1
H1A3 H -0.329633 0.982546 -0.001794 0.135 Uiso 0.440(5) 1 calc R U P A -1
C2A C -0.117(2) 1.0289(11) 0.0516(8) 0.053(4) Uani 0.440(5) 1 d . . P A -1
H2A1 H -0.079592 1.089321 0.080013 0.064 Uiso 0.440(5) 1 calc R U P A -1
H2A2 H -0.115330 0.971434 0.086613 0.064 Uiso 0.440(5) 1 calc R U P A -1
C3A C 0.140(2) 0.9834(13) 0.0211(10) 0.063(5) Uani 0.440(5) 1 d . . P A -1
H3A1 H 0.190903 1.041933 0.047106 0.076 Uiso 0.440(5) 1 calc R U P A -1
H3A2 H 0.139773 0.927564 0.057616 0.076 Uiso 0.440(5) 1 calc R U P A -1
C4A C 0.229(3) 0.954(3) -0.038(2) 0.087(11) Uani 0.440(5) 1 d . . P A -1
H4A1 H 0.225246 1.007417 -0.075562 0.131 Uiso 0.440(5) 1 calc R U P A -1
H4A2 H 0.185774 0.891945 -0.060526 0.131 Uiso 0.440(5) 1 calc R U P A -1
H4A3 H 0.337910 0.942738 -0.018068 0.131 Uiso 0.440(5) 1 calc R U P A -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 N1 1.969(4) . ?
Cu1 N4 1.970(3) 3_575 ?
Cu1 Cl1 2.2615(11) . ?
Cu1 Cl2 2.2860(11) . ?
N3 C15 1.347(5) . ?
N3 C13 1.386(5) . ?
N3 C12 1.465(5) . ?
N4 C15 1.328(5) . ?
N4 C14 1.385(5) . ?
N1 C3 1.340(5) . ?
N1 C1 1.386(5) . ?
N2 C3 1.349(5) . ?
N2 C2 1.373(6) . ?
N2 C5 1.466(5) . ?
C6 C11 1.374(6) . ?
C6 C7 1.394(6) . ?
C6 C5 1.517(6) . ?
C16 C15 1.491(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C3 C4 1.477(6) . ?
C9 C10 1.388(6) . ?
C9 C8 1.393(6) . ?
C9 C12 1.513(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C1 C2 1.341(6) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C7 C8 1.385(6) . ?
C7 H7 0.9500 . ?
C13 C14 1.356(6) . ?
C13 H13 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.394(7) . ?
C10 H10 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C11 H11 0.9500 . ?
C14 H14 0.9500 . ?
O1A C2A 1.36(4) . ?
O1A C3A 1.45(2) . ?
C1A C2A 1.53(3) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C4A 1.42(4) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A H4A1 0.9800 . ?
C4A H4A2 0.9800 . ?
C4A H4A3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N4 148.26(14) . 3_575 ?
N1 Cu1 Cl1 96.68(11) . . ?
N4 Cu1 Cl1 94.84(10) 3_575 . ?
N1 Cu1 Cl2 98.29(11) . . ?
N4 Cu1 Cl2 97.32(10) 3_575 . ?
Cl1 Cu1 Cl2 128.68(5) . . ?
C15 N3 C13 107.7(3) . . ?
C15 N3 C12 127.1(4) . . ?
C13 N3 C12 125.2(3) . . ?
C15 N4 C14 107.0(3) . . ?
C15 N4 Cu1 126.7(3) . 3_575 ?
C14 N4 Cu1 126.1(3) . 3_575 ?
C3 N1 C1 106.3(4) . . ?
C3 N1 Cu1 128.7(3) . . ?
C1 N1 Cu1 125.0(3) . . ?
C3 N2 C2 108.0(4) . . ?
C3 N2 C5 126.5(4) . . ?
C2 N2 C5 125.4(4) . . ?
C11 C6 C7 119.3(4) . . ?
C11 C6 C5 121.0(4) . . ?
C7 C6 C5 119.7(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C3 N2 109.6(4) . . ?
N1 C3 C4 127.2(4) . . ?
N2 C3 C4 123.1(4) . . ?
C10 C9 C8 118.3(4) . . ?
C10 C9 C12 122.6(4) . . ?
C8 C9 C12 119.0(4) . . ?
N2 C5 C6 112.8(3) . . ?
N2 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N3 C12 C9 113.5(4) . . ?
N3 C12 H12A 108.9 . . ?
C9 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C9 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C2 C1 N1 109.2(4) . . ?
C2 C1 H1 125.4 . . ?
N1 C1 H1 125.4 . . ?
C1 C2 N2 107.0(4) . . ?
C1 C2 H2 126.5 . . ?
N2 C2 H2 126.5 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C14 C13 N3 106.5(4) . . ?
C14 C13 H13 126.7 . . ?
N3 C13 H13 126.7 . . ?
C7 C8 C9 120.9(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C11 C10 120.4(4) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C14 N4 108.7(4) . . ?
C13 C14 H14 125.7 . . ?
N4 C14 H14 125.7 . . ?
N4 C15 N3 110.1(4) . . ?
N4 C15 C16 126.3(4) . . ?
N3 C15 C16 123.6(4) . . ?
C2A O1A C3A 117(3) . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
O1A C2A C1A 110(2) . . ?
O1A C2A H2A1 109.6 . . ?
C1A C2A H2A1 109.6 . . ?
O1A C2A H2A2 109.6 . . ?
C1A C2A H2A2 109.6 . . ?
H2A1 C2A H2A2 108.2 . . ?
C4A C3A O1A 114(2) . . ?
C4A C3A H3A1 108.8 . . ?
O1A C3A H3A1 108.8 . . ?
C4A C3A H3A2 108.8 . . ?
O1A C3A H3A2 108.8 . . ?
H3A1 C3A H3A2 107.7 . . ?
C3A C4A H4A1 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?

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
C1 N1 C3 N2 -0.8(5) . . . . ?
Cu1 N1 C3 N2 -179.4(3) . . . . ?
C1 N1 C3 C4 178.2(5) . . . . ?
Cu1 N1 C3 C4 -0.4(7) . . . . ?
C2 N2 C3 N1 0.3(5) . . . . ?
C5 N2 C3 N1 177.0(4) . . . . ?
C2 N2 C3 C4 -178.8(5) . . . . ?
C5 N2 C3 C4 -2.1(7) . . . . ?
C3 N2 C5 C6 -82.9(5) . . . . ?
C2 N2 C5 C6 93.2(5) . . . . ?
C11 C6 C5 N2 109.0(5) . . . . ?
C7 C6 C5 N2 -70.5(5) . . . . ?
C15 N3 C12 C9 -74.0(5) . . . . ?
C13 N3 C12 C9 107.0(4) . . . . ?
C10 C9 C12 N3 -34.5(6) . . . . ?
C8 C9 C12 N3 148.5(4) . . . . ?
C3 N1 C1 C2 1.1(5) . . . . ?
Cu1 N1 C1 C2 179.7(3) . . . . ?
N1 C1 C2 N2 -0.9(5) . . . . ?
C3 N2 C2 C1 0.4(5) . . . . ?
C5 N2 C2 C1 -176.4(4) . . . . ?
C11 C6 C7 C8 -0.1(6) . . . . ?
C5 C6 C7 C8 179.4(4) . . . . ?
C15 N3 C13 C14 0.4(5) . . . . ?
C12 N3 C13 C14 179.5(4) . . . . ?
C6 C7 C8 C9 0.6(7) . . . . ?
C10 C9 C8 C7 -0.9(6) . . . . ?
C12 C9 C8 C7 176.2(4) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C12 C9 C10 C11 -176.2(4) . . . . ?
C7 C6 C11 C10 -0.1(7) . . . . ?
C5 C6 C11 C10 -179.6(4) . . . . ?
C9 C10 C11 C6 -0.3(7) . . . . ?
N3 C13 C14 N4 -1.0(5) . . . . ?
C15 N4 C14 C13 1.1(5) . . . . ?
Cu1 N4 C14 C13 -173.6(3) 3_575 . . . ?
C14 N4 C15 N3 -0.9(5) . . . . ?
Cu1 N4 C15 N3 173.8(3) 3_575 . . . ?
C14 N4 C15 C16 179.7(4) . . . . ?
Cu1 N4 C15 C16 -5.6(6) 3_575 . . . ?
C13 N3 C15 N4 0.3(5) . . . . ?
C12 N3 C15 N4 -178.8(4) . . . . ?
C13 N3 C15 C16 179.8(4) . . . . ?
C12 N3 C15 C16 0.7(7) . . . . ?
C3A O1A C2A C1A -175(3) . . . . ?
C2A O1A C3A C4A 174(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
C16 H16A Cl2 0.98 2.89 3.637(5) 133.5 3_575
C16 H16B O1A 0.98 2.55 3.51(4) 169.4 .
C16 H16C Cl1 0.98 2.86 3.659(5) 139.4 3_675
C5 H5A Cl2 0.99 2.96 3.829(5) 147.1 2_655
C5 H5A Cl1 0.99 2.87 3.453(4) 118.5 2_655
C12 H12A Cl2 0.99 2.79 3.734(5) 159.0 1_565
C12 H12B Cl1 0.99 2.64 3.605(4) 165.8 3_675
C1 H1 Cl1 0.95 2.72 3.224(5) 114.1 .
C13 H13 Cl2 0.95 2.88 3.641(5) 138.0 1_565
C4 H4C Cl2 0.98 2.68 3.459(6) 137.1 .
C14 H14 Cl1 0.95 2.97 3.786(4) 144.5 1_465
C14 H14 Cl1 0.95 2.75 3.220(4) 111.5 3_575

_refine_diff_density_max         0.757
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.119



####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1818832'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            6
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H36 Cl4 Cu2 N8, 0.998(C5 H12)'
_chemical_formula_sum            'C36.99 H47.97 Cl4 Cu2 N8'
_chemical_formula_weight         873.56

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                   8.499(4)
_cell_length_b                   13.247(6)
_cell_length_c                   18.335(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.452(9)
_cell_angle_gamma                90
_cell_volume                     2055.1(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2434
_cell_measurement_theta_min      2.2315
_cell_measurement_theta_max      21.609

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             903.8
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    1.332
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6510
_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_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32277
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.899
_diffrn_reflns_theta_max         28.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5121
_reflns_number_gt                3688
_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    'SHELXS-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)+(0.0413P)²+2.3511P] 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         5121
_refine_ls_number_parameters     234
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.019
_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 0.30893(4) 0.70044(3) 0.09855(2) 0.01774(12) Uani 1 1 d . . . . .
Cl2 Cl 0.17131(9) 0.62988(6) 0.18701(4) 0.02131(18) Uani 1 1 d . . . . .
Cl1 Cl 0.53513(9) 0.64870(6) 0.05479(5) 0.02537(19) Uani 1 1 d . . . . .
N3 N 0.0436(3) 1.38574(19) 0.05799(14) 0.0195(6) Uani 1 1 d . . . . .
N2 N 0.4352(3) 0.9490(2) 0.22791(14) 0.0203(6) Uani 1 1 d . . . . .
N1 N 0.4008(3) 0.8156(2) 0.15650(15) 0.0195(6) Uani 1 1 d . . . . .
N4 N -0.1705(3) 1.34966(19) -0.01422(14) 0.0187(6) Uani 1 1 d . . . . .
C9 C 0.2537(4) 1.2936(2) 0.13628(17) 0.0186(6) Uani 1 1 d . . . . .
C6 C 0.3488(4) 1.1280(2) 0.22587(17) 0.0204(7) Uani 1 1 d . . . . .
C2 C 0.5821(4) 0.9224(2) 0.20840(18) 0.0211(7) Uani 1 1 d . . . . .
H2 H 0.679369 0.955325 0.222782 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4578(4) 1.1793(2) 0.18684(18) 0.0211(7) Uani 1 1 d . . . . .
H7 H 0.565186 1.158430 0.190964 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2098(4) 1.3858(2) 0.08979(18) 0.0204(7) Uani 1 1 d . . . . .
H12A H 0.228997 1.447046 0.120321 0.024 Uiso 1 1 calc R U . . .
H12B H 0.279555 1.389344 0.049581 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3273(4) 0.8837(2) 0.19517(18) 0.0199(7) Uani 1 1 d . . . . .
C8 C 0.4103(4) 1.2608(2) 0.14203(18) 0.0209(7) Uani 1 1 d . . . . .
H8 H 0.485100 1.294229 0.115179 0.025 Uiso 1 1 calc R U . . .
C13 C -0.0753(4) 1.4454(2) 0.08031(18) 0.0213(7) Uani 1 1 d . . . . .
H13 H -0.066339 1.493339 0.119014 0.026 Uiso 1 1 calc R U . . .
C1 C 0.5608(4) 0.8400(2) 0.16466(18) 0.0212(7) Uani 1 1 d . . . . .
H1 H 0.641967 0.804643 0.143100 0.025 Uiso 1 1 calc R U . . .
C11 C 0.1926(4) 1.1605(2) 0.21940(19) 0.0240(7) Uani 1 1 d . . . . .
H11 H 0.117110 1.126269 0.245343 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1454(4) 1.2431(3) 0.17518(19) 0.0248(7) Uani 1 1 d . . . . .
H10 H 0.038457 1.264817 0.171704 0.030 Uiso 1 1 calc R U . . .
C14 C -0.2084(4) 1.4224(2) 0.03610(18) 0.0201(7) Uani 1 1 d . . . . .
H14 H -0.309961 1.451100 0.039101 0.024 Uiso 1 1 calc R U . . .
C5 C 0.4006(4) 1.0376(2) 0.27237(18) 0.0224(7) Uani 1 1 d . . . . .
H5A H 0.496344 1.055542 0.304805 0.027 Uiso 1 1 calc R U . . .
H5B H 0.316232 1.019931 0.303811 0.027 Uiso 1 1 calc R U . . .
C16 C 0.0759(4) 1.2552(3) -0.0386(2) 0.0292(8) Uani 1 1 d . . . . .
H16A H 0.008428 1.197911 -0.054744 0.044 Uiso 1 1 calc R U . . .
H16B H 0.165464 1.231166 -0.005526 0.044 Uiso 1 1 calc R U . . .
H16C H 0.115142 1.287813 -0.081252 0.044 Uiso 1 1 calc R U . . .
C15 C -0.0172(4) 1.3291(2) 0.00063(18) 0.0197(7) Uani 1 1 d . . . . .
C4 C 0.1541(4) 0.8913(3) 0.2016(2) 0.0278(8) Uani 1 1 d . . . . .
H4A H 0.108954 0.944738 0.169076 0.042 Uiso 1 1 calc R U . . .
H4B H 0.136229 0.907440 0.252335 0.042 Uiso 1 1 calc R U . . .
H4C H 0.103348 0.826835 0.187670 0.042 Uiso 1 1 calc R U . . .
C5A C -0.2003(13) 1.0398(10) 0.0219(8) 0.118(5) Uani 0.499(4) 1 d D . P A -1
H5A1 H -0.175110 0.971196 0.039352 0.178 Uiso 0.499(4) 1 calc R U P A -1
H5A2 H -0.132509 1.088203 0.050454 0.178 Uiso 0.499(4) 1 calc R U P A -1
H5A3 H -0.182089 1.045020 -0.029968 0.178 Uiso 0.499(4) 1 calc R U P A -1
C2A C -0.6436(12) 1.0081(12) 0.0032(9) 0.118(5) Uani 0.499(4) 1 d D . P A -1
H2A1 H -0.669392 1.078370 -0.012046 0.142 Uiso 0.499(4) 1 calc R U P A -1
H2A2 H -0.655405 1.001718 0.056207 0.142 Uiso 0.499(4) 1 calc R U P A -1
C1A C -0.754(2) 0.9336(12) -0.0409(9) 0.118(5) Uani 0.499(4) 1 d D . P A -1
H1A1 H -0.736323 0.937365 -0.092791 0.178 Uiso 0.499(4) 1 calc R U P A -1
H1A2 H -0.864497 0.951227 -0.035039 0.178 Uiso 0.499(4) 1 calc R U P A -1
H1A3 H -0.732897 0.864915 -0.022816 0.178 Uiso 0.499(4) 1 calc R U P A -1
C4A C -0.3746(15) 1.0631(9) 0.0310(8) 0.118(5) Uani 0.499(4) 1 d D . P A -1
H4A1 H -0.402918 1.131130 0.011590 0.142 Uiso 0.499(4) 1 calc R U P A -1
H4A2 H -0.393666 1.060928 0.083405 0.142 Uiso 0.499(4) 1 calc R U P A -1
C3A C -0.4736(12) 0.9820(11) -0.0123(9) 0.118(5) Uani 0.499(4) 1 d D . P A -1
H3A1 H -0.460814 0.986192 -0.065305 0.142 Uiso 0.499(4) 1 calc R U P A -1
H3A2 H -0.443835 0.913373 0.005513 0.142 Uiso 0.499(4) 1 calc R U P A -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 N4 1.967(3) 3_575 ?
Cu1 N1 1.976(3) . ?
Cu1 Cl1 2.2590(12) . ?
Cu1 Cl2 2.2875(11) . ?
N3 C15 1.354(4) . ?
N3 C13 1.376(4) . ?
N3 C12 1.476(4) . ?
N2 C3 1.359(4) . ?
N2 C2 1.376(4) . ?
N2 C5 1.474(4) . ?
N1 C3 1.338(4) . ?
N1 C1 1.393(4) . ?
N4 C15 1.333(4) . ?
N4 C14 1.393(4) . ?
C9 C10 1.388(5) . ?
C9 C8 1.395(4) . ?
C9 C12 1.516(4) . ?
C6 C11 1.390(5) . ?
C6 C7 1.399(5) . ?
C6 C5 1.511(4) . ?
C2 C1 1.357(4) . ?
C2 H2 0.9500 . ?
C7 C8 1.392(4) . ?
C7 H7 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C3 C4 1.491(5) . ?
C8 H8 0.9500 . ?
C13 C14 1.362(4) . ?
C13 H13 0.9500 . ?
C1 H1 0.9500 . ?
C11 C10 1.397(5) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C14 H14 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C16 C15 1.486(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5A C4A 1.538(2) . ?
C5A H5A1 0.9800 . ?
C5A H5A2 0.9800 . ?
C5A H5A3 0.9800 . ?
C2A C3A 1.539(2) . ?
C2A C1A 1.539(2) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
C4A C3A 1.539(2) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?

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 149.21(11) 3_575 . ?
N4 Cu1 Cl1 94.83(9) 3_575 . ?
N1 Cu1 Cl1 96.84(9) . . ?
N4 Cu1 Cl2 96.40(9) 3_575 . ?
N1 Cu1 Cl2 97.85(9) . . ?
Cl1 Cu1 Cl2 129.62(4) . . ?
C15 N3 C13 108.2(3) . . ?
C15 N3 C12 126.0(3) . . ?
C13 N3 C12 125.8(3) . . ?
C3 N2 C2 108.2(3) . . ?
C3 N2 C5 126.1(3) . . ?
C2 N2 C5 125.5(3) . . ?
C3 N1 C1 106.7(3) . . ?
C3 N1 Cu1 128.7(2) . . ?
C1 N1 Cu1 124.7(2) . . ?
C15 N4 C14 106.8(3) . . ?
C15 N4 Cu1 126.2(2) . 3_575 ?
C14 N4 Cu1 126.5(2) . 3_575 ?
C10 C9 C8 119.1(3) . . ?
C10 C9 C12 122.5(3) . . ?
C8 C9 C12 118.4(3) . . ?
C11 C6 C7 118.6(3) . . ?
C11 C6 C5 121.2(3) . . ?
C7 C6 C5 120.1(3) . . ?
C1 C2 N2 106.7(3) . . ?
C1 C2 H2 126.7 . . ?
N2 C2 H2 126.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N3 C12 C9 113.4(3) . . ?
N3 C12 H12A 108.9 . . ?
C9 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C9 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
N1 C3 N2 109.5(3) . . ?
N1 C3 C4 127.0(3) . . ?
N2 C3 C4 123.5(3) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C14 C13 N3 106.7(3) . . ?
C14 C13 H13 126.7 . . ?
N3 C13 H13 126.7 . . ?
C2 C1 N1 108.9(3) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C6 C11 C10 120.8(3) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C13 C14 N4 108.5(3) . . ?
C13 C14 H14 125.7 . . ?
N4 C14 H14 125.7 . . ?
N2 C5 C6 112.4(3) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C15 N3 109.8(3) . . ?
N4 C15 C16 126.2(3) . . ?
N3 C15 C16 124.0(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C4A C5A H5A1 109.5 . . ?
C4A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C4A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
C3A C2A C1A 107.3(11) . . ?
C3A C2A H2A1 110.3 . . ?
C1A C2A H2A1 110.3 . . ?
C3A C2A H2A2 110.3 . . ?
C1A C2A H2A2 110.3 . . ?
H2A1 C2A H2A2 108.5 . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
C5A C4A C3A 106.78(19) . . ?
C5A C4A H4A1 110.4 . . ?
C3A C4A H4A1 110.4 . . ?
C5A C4A H4A2 110.4 . . ?
C3A C4A H4A2 110.4 . . ?
H4A1 C4A H4A2 108.6 . . ?
C2A C3A C4A 103.0(8) . . ?
C2A C3A H3A1 111.2 . . ?
C4A C3A H3A1 111.2 . . ?
C2A C3A H3A2 111.2 . . ?
C4A C3A H3A2 111.2 . . ?
H3A1 C3A H3A2 109.1 . . ?

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
C3 N2 C2 C1 -0.8(3) . . . . ?
C5 N2 C2 C1 -176.8(3) . . . . ?
C11 C6 C7 C8 -0.5(5) . . . . ?
C5 C6 C7 C8 178.0(3) . . . . ?
C15 N3 C12 C9 -75.3(4) . . . . ?
C13 N3 C12 C9 106.6(3) . . . . ?
C10 C9 C12 N3 -30.6(4) . . . . ?
C8 C9 C12 N3 151.8(3) . . . . ?
C1 N1 C3 N2 -0.7(3) . . . . ?
Cu1 N1 C3 N2 178.9(2) . . . . ?
C1 N1 C3 C4 177.9(3) . . . . ?
Cu1 N1 C3 C4 -2.5(5) . . . . ?
C2 N2 C3 N1 1.0(4) . . . . ?
C5 N2 C3 N1 177.0(3) . . . . ?
C2 N2 C3 C4 -177.7(3) . . . . ?
C5 N2 C3 C4 -1.7(5) . . . . ?
C6 C7 C8 C9 1.1(5) . . . . ?
C10 C9 C8 C7 -0.8(5) . . . . ?
C12 C9 C8 C7 176.9(3) . . . . ?
C15 N3 C13 C14 0.9(4) . . . . ?
C12 N3 C13 C14 179.2(3) . . . . ?
N2 C2 C1 N1 0.4(4) . . . . ?
C3 N1 C1 C2 0.2(4) . . . . ?
Cu1 N1 C1 C2 -179.4(2) . . . . ?
C7 C6 C11 C10 -0.3(5) . . . . ?
C5 C6 C11 C10 -178.8(3) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C12 C9 C10 C11 -177.7(3) . . . . ?
C6 C11 C10 C9 0.6(5) . . . . ?
N3 C13 C14 N4 -1.0(4) . . . . ?
C15 N4 C14 C13 0.7(4) . . . . ?
Cu1 N4 C14 C13 -172.3(2) 3_575 . . . ?
C3 N2 C5 C6 -80.9(4) . . . . ?
C2 N2 C5 C6 94.4(4) . . . . ?
C11 C6 C5 N2 107.8(3) . . . . ?
C7 C6 C5 N2 -70.7(4) . . . . ?
C14 N4 C15 N3 -0.2(4) . . . . ?
Cu1 N4 C15 N3 172.9(2) 3_575 . . . ?
C14 N4 C15 C16 179.6(3) . . . . ?
Cu1 N4 C15 C16 -7.4(5) 3_575 . . . ?
C13 N3 C15 N4 -0.4(4) . . . . ?
C12 N3 C15 N4 -178.8(3) . . . . ?
C13 N3 C15 C16 179.8(3) . . . . ?
C12 N3 C15 C16 1.5(5) . . . . ?
C1A C2A C3A C4A 177.4(13) . . . . ?
C5A C4A C3A C2A 177.2(11) . . . . ?

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
C12 H12A Cl2 0.99 2.78 3.721(4) 159.5 1_565
C12 H12B Cl1 0.99 2.64 3.609(4) 166.3 3_675
C13 H13 Cl2 0.95 2.90 3.663(3) 137.8 1_565
C1 H1 Cl1 0.95 2.73 3.231(4) 114.0 .
C14 H14 Cl1 0.95 2.96 3.742(3) 140.9 1_465
C14 H14 Cl1 0.95 2.78 3.240(3) 110.4 3_575
C5 H5A Cl2 0.99 2.98 3.843(4) 146.1 2_655
C5 H5A Cl1 0.99 2.89 3.490(4) 119.8 2_655
C4 H4C Cl2 0.98 2.67 3.478(4) 139.7 .

_refine_diff_density_max         0.927
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.101



