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

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

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

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

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

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

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

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

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

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.175
_exptl_absorpt_coefficient_mu    1.422
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.789
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_T_max  0.7890
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10547
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         28.241
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4412
_reflns_number_gt                2788
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4412
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.928
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.02295(5) 0.72357(4) 0.40190(2) 0.01757(13) Uani 1 1 d . . . . .
Cl1 Cl 0.16076(11) 0.68523(9) 0.32344(4) 0.0242(2) Uani 1 1 d . . . . .
Cl2 Cl -0.12225(11) 0.85838(10) 0.45279(4) 0.0299(2) Uani 1 1 d . . . . .
N4 N 0.1715(4) 0.3691(3) 0.63693(13) 0.0193(7) Uani 1 1 d . . . . .
N1 N 0.2248(4) 0.7537(3) 0.45933(12) 0.0202(7) Uani 1 1 d . . . . .
N3 N 0.3320(3) 0.4985(3) 0.69574(12) 0.0176(6) Uani 1 1 d . . . . .
C5 C 0.5418(4) 0.8459(3) 0.63643(14) 0.0144(7) Uani 1 1 d . . . . .
C8 C 0.7704(4) 0.7646(3) 0.70416(14) 0.0173(8) Uani 1 1 d . . . . .
H8 H 0.883836 0.764078 0.718304 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4745(4) 0.9238(3) 0.58060(15) 0.0203(8) Uani 1 1 d . . . . .
H4A H 0.390104 0.982955 0.590968 0.024 Uiso 1 1 calc R U . . .
H4B H 0.562617 0.975137 0.567362 0.024 Uiso 1 1 calc R U . . .
C13 C 0.2555(4) 0.7759(4) 0.64580(15) 0.0216(8) Uani 1 1 d . . . . .
H13A H 0.225828 0.858334 0.626567 0.032 Uiso 1 1 calc R U . . .
H13B H 0.199641 0.765153 0.681295 0.032 Uiso 1 1 calc R U . . .
H13C H 0.223371 0.707209 0.616587 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4373(4) 0.7712(3) 0.66581(14) 0.0153(7) Uani 1 1 d . . . . .
N2 N 0.4036(3) 0.8391(3) 0.53059(12) 0.0185(7) Uani 1 1 d . . . . .
C3 C 0.2506(4) 0.8459(3) 0.50023(15) 0.0184(8) Uani 1 1 d . . . . .
H3 H 0.172610 0.908104 0.507291 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5021(4) 0.6886(3) 0.71320(14) 0.0148(7) Uani 1 1 d . . . . .
C9 C 0.6710(4) 0.6841(3) 0.73183(14) 0.0161(8) Uani 1 1 d . . . . .
C2 C 0.4771(5) 0.7359(4) 0.50827(16) 0.0264(9) Uani 1 1 d . . . . .
H2 H 0.584626 0.706507 0.521074 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7110(4) 0.8459(3) 0.65661(15) 0.0165(8) Uani 1 1 d . . . . .
C10 C 0.7486(5) 0.5915(4) 0.77999(16) 0.0252(9) Uani 1 1 d . . . . .
H10A H 0.866351 0.604952 0.787166 0.038 Uiso 1 1 calc R U . . .
H10B H 0.725280 0.503862 0.766018 0.038 Uiso 1 1 calc R U . . .
H10C H 0.704306 0.605717 0.817895 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3913(4) 0.5981(3) 0.74008(15) 0.0197(8) Uani 1 1 d . . . . .
H14A H 0.450903 0.558243 0.777213 0.024 Uiso 1 1 calc R U . . .
H14B H 0.297995 0.645742 0.751715 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1790(4) 0.4590(3) 0.67920(14) 0.0170(8) Uani 1 1 d . . . . .
H17 H 0.087924 0.491015 0.695572 0.020 Uiso 1 1 calc R U . . .
C7 C 0.8280(4) 0.9307(4) 0.62894(16) 0.0253(9) Uani 1 1 d . . . . .
H7A H 0.937833 0.919637 0.651262 0.038 Uiso 1 1 calc R U . . .
H7B H 0.794888 1.019914 0.631466 0.038 Uiso 1 1 calc R U . . .
H7C H 0.827128 0.907235 0.586205 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4290(5) 0.4290(4) 0.66306(17) 0.0243(9) Uani 1 1 d . . . . .
H15 H 0.543619 0.435210 0.665381 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3293(5) 0.3504(4) 0.62708(16) 0.0244(9) Uani 1 1 d . . . . .
H16 H 0.362591 0.291042 0.599118 0.029 Uiso 1 1 calc R U . . .
C1 C 0.3656(5) 0.6841(4) 0.46428(17) 0.0289(10) Uani 1 1 d . . . . .
H1 H 0.382518 0.611205 0.440649 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.974(3) 3_566 ?
Cu1 N1 1.979(3) . ?
Cu1 Cl1 2.2614(10) . ?
Cu1 Cl2 2.2687(11) . ?
N4 C17 1.325(4) . ?
N4 C16 1.378(5) . ?
N1 C3 1.323(4) . ?
N1 C1 1.372(5) . ?
N3 C17 1.338(4) . ?
N3 C15 1.373(4) . ?
N3 C14 1.470(4) . ?
C5 C12 1.402(5) . ?
C5 C6 1.414(5) . ?
C5 C4 1.521(4) . ?
C8 C9 1.389(5) . ?
C8 C6 1.391(5) . ?
C8 H8 0.9500 . ?
C4 N2 1.475(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C13 C12 1.514(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 C11 1.408(5) . ?
N2 C3 1.352(4) . ?
N2 C2 1.372(5) . ?
C3 H3 0.9500 . ?
C11 C9 1.406(5) . ?
C11 C14 1.508(5) . ?
C9 C10 1.517(5) . ?
C2 C1 1.357(5) . ?
C2 H2 0.9500 . ?
C6 C7 1.516(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 H17 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 C16 1.346(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C1 H1 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 N1 157.44(12) 3_566 . ?
N4 Cu1 Cl1 93.01(9) 3_566 . ?
N1 Cu1 Cl1 92.65(9) . . ?
N4 Cu1 Cl2 93.54(9) 3_566 . ?
N1 Cu1 Cl2 92.48(9) . . ?
Cl1 Cu1 Cl2 149.81(4) . . ?
C17 N4 C16 105.6(3) . . ?
C17 N4 Cu1 127.5(2) . 3_566 ?
C16 N4 Cu1 126.9(2) . 3_566 ?
C3 N1 C1 106.5(3) . . ?
C3 N1 Cu1 126.6(2) . . ?
C1 N1 Cu1 126.9(2) . . ?
C17 N3 C15 107.5(3) . . ?
C17 N3 C14 128.0(3) . . ?
C15 N3 C14 124.5(3) . . ?
C12 C5 C6 120.7(3) . . ?
C12 C5 C4 120.1(3) . . ?
C6 C5 C4 119.2(3) . . ?
C9 C8 C6 122.8(3) . . ?
C9 C8 H8 118.6 . . ?
C6 C8 H8 118.6 . . ?
N2 C4 C5 110.4(3) . . ?
N2 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C12 C11 119.8(3) . . ?
C5 C12 C13 120.5(3) . . ?
C11 C12 C13 119.7(3) . . ?
C3 N2 C2 107.4(3) . . ?
C3 N2 C4 125.9(3) . . ?
C2 N2 C4 126.7(3) . . ?
N1 C3 N2 110.4(3) . . ?
N1 C3 H3 124.8 . . ?
N2 C3 H3 124.8 . . ?
C9 C11 C12 119.8(3) . . ?
C9 C11 C14 120.4(3) . . ?
C12 C11 C14 119.6(3) . . ?
C8 C9 C11 119.0(3) . . ?
C8 C9 C10 118.8(3) . . ?
C11 C9 C10 122.1(3) . . ?
C1 C2 N2 106.4(3) . . ?
C1 C2 H2 126.8 . . ?
N2 C2 H2 126.8 . . ?
C8 C6 C5 117.8(3) . . ?
C8 C6 C7 119.4(3) . . ?
C5 C6 C7 122.8(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C14 C11 110.3(3) . . ?
N3 C14 H14A 109.6 . . ?
C11 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C11 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N4 C17 N3 111.0(3) . . ?
N4 C17 H17 124.5 . . ?
N3 C17 H17 124.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C15 N3 106.2(3) . . ?
C16 C15 H15 126.9 . . ?
N3 C15 H15 126.9 . . ?
C15 C16 N4 109.7(3) . . ?
C15 C16 H16 125.1 . . ?
N4 C16 H16 125.1 . . ?
C2 C1 N1 109.3(3) . . ?
C2 C1 H1 125.4 . . ?
N1 C1 H1 125.4 . . ?

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

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

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.099

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
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# Please retain this information to preserve the provenance of 
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data_7
_database_code_depnum_ccdc_archive 'CCDC 1569716'
_audit_update_record             
;
2017-09-15 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_7                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.915 Note
RESPONSE: Owing to the inclusion of such a large guest the crystal quality deteriorates thus a complete data set could not be obtained
;
_vrf_PLAT911_7                   
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.600        327 Report
RESPONSE: Owing to the inclusion of such a large guest the crystal quality deteriorates thus a complete data set could not be obtained
;
# Added during the CSD deposition process: Friday 15 September 2017 01:05 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            7
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, C6 H4 F2'
_chemical_formula_sum            'C40 H44 Cl4 Cu2 F2 N8'
_chemical_formula_weight         943.71

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'
F F 0.0171 0.0103 '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                   8.424(2)
_cell_length_b                   10.944(3)
_cell_length_c                   22.094(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.735(5)
_cell_angle_gamma                90
_cell_volume                     2007.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3790
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      27.92

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.377
_shelx_estimated_absorpt_T_min   0.492
_shelx_estimated_absorpt_T_max   0.770
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4922
_exptl_absorpt_correction_T_max  0.7703
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4987
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.083
_diffrn_reflns_theta_max         27.918
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.788
_diffrn_measured_fraction_theta_full 0.915
_diffrn_reflns_Laue_measured_fraction_max 0.788
_diffrn_reflns_Laue_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_point_group_measured_fraction_full 0.915
_reflns_number_total             3790
_reflns_number_gt                2588
_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 acknowlede the presence of A and B alerts assosciated
with a low data completeness. This is as a result of poor crystal quality
upon uptake of such a large guest.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+8.7759P] 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         3790
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.02355(9) 0.75993(7) 0.39526(3) 0.0215(2) Uani 1 1 d . . . . .
Cl1 Cl 0.15599(18) 0.80481(16) 0.31702(7) 0.0273(4) Uani 1 1 d . . . . .
Cl2 Cl -0.12264(18) 0.63310(16) 0.44553(8) 0.0318(4) Uani 1 1 d . . . . .
N4 N 0.1679(6) 1.1452(5) 0.6422(2) 0.0215(11) Uani 1 1 d . . . . .
N2 N 0.3937(6) 0.6411(5) 0.5296(2) 0.0228(12) Uani 1 1 d . . . . .
N1 N 0.2246(6) 0.7137(5) 0.4511(2) 0.0248(12) Uani 1 1 d . . . . .
N3 N 0.3261(6) 1.0065(5) 0.6946(2) 0.0229(12) Uani 1 1 d . . . . .
C3 C 0.2421(7) 0.6388(6) 0.4990(3) 0.0231(14) Uani 1 1 d . . . . .
H3 H 0.158328 0.589981 0.510074 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5274(7) 0.6574(6) 0.6379(3) 0.0194(13) Uani 1 1 d . . . . .
C12 C 0.6956(7) 0.6653(5) 0.6564(3) 0.0196(13) Uani 1 1 d . . . . .
C14 C 0.3833(8) 0.9062(6) 0.7376(3) 0.0249(14) Uani 1 1 d . . . . .
H14A H 0.289577 0.860401 0.747451 0.030 Uiso 1 1 calc R U . . .
H14B H 0.442745 0.940840 0.776242 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2428(7) 0.7197(6) 0.6508(3) 0.0293(15) Uani 1 1 d . . . . .
H7A H 0.196884 0.793101 0.629152 0.044 Uiso 1 1 calc R U . . .
H7B H 0.198504 0.709731 0.688760 0.044 Uiso 1 1 calc R U . . .
H7C H 0.215611 0.648044 0.624507 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4792(8) 0.7224(8) 0.5000(3) 0.0401(19) Uani 1 1 d . . . . .
H2 H 0.589584 0.743705 0.511331 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8106(8) 0.5833(6) 0.6294(3) 0.0304(16) Uani 1 1 d . . . . .
H13A H 0.921017 0.598405 0.650358 0.046 Uiso 1 1 calc R U . . .
H13B H 0.802938 0.600863 0.585508 0.046 Uiso 1 1 calc R U . . .
H13C H 0.782433 0.497624 0.634901 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4568(7) 0.5725(6) 0.5859(3) 0.0230(14) Uani 1 1 d . . . . .
H4A H 0.541062 0.514994 0.577414 0.028 Uiso 1 1 calc R U . . .
H4B H 0.368746 0.523957 0.598591 0.028 Uiso 1 1 calc R U . . .
C17 C 0.1755(7) 1.0510(5) 0.6809(3) 0.0195(13) Uani 1 1 d . . . . .
H17 H 0.085876 1.019379 0.696746 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6598(7) 0.8283(5) 0.7275(3) 0.0225(13) Uani 1 1 d . . . . .
C8 C 0.4925(7) 0.8196(6) 0.7100(3) 0.0218(13) Uani 1 1 d . . . . .
C6 C 0.4262(7) 0.7327(5) 0.6664(3) 0.0198(13) Uani 1 1 d . . . . .
C11 C 0.7577(7) 0.7480(6) 0.7009(3) 0.0212(13) Uani 1 1 d . . . . .
H11 H 0.870963 0.750763 0.714207 0.025 Uiso 1 1 calc R U . . .
C16 C 0.3248(8) 1.1606(6) 0.6316(3) 0.0291(16) Uani 1 1 d . . . . .
H16 H 0.358748 1.221488 0.605867 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7388(8) 0.9195(6) 0.7743(3) 0.0297(15) Uani 1 1 d . . . . .
H10A H 0.708619 1.002460 0.760162 0.045 Uiso 1 1 calc R U . . .
H10B H 0.856066 0.910428 0.779593 0.045 Uiso 1 1 calc R U . . .
H10C H 0.702984 0.904764 0.813652 0.045 Uiso 1 1 calc R U . . .
C1 C 0.3751(7) 0.7658(7) 0.4515(3) 0.0333(17) Uani 1 1 d . . . . .
H1 H 0.400711 0.822975 0.422280 0.040 Uiso 1 1 calc R U . . .
C15 C 0.4218(8) 1.0756(6) 0.6635(3) 0.0302(16) Uani 1 1 d . . . . .
H15 H 0.534113 1.065782 0.664156 0.036 Uiso 1 1 calc R U . . .
F1A F 0.2976(7) 1.0530(6) 0.4755(3) 0.0876(19) Uani 1 1 d . . . . .
C1A C 0.1446(11) 1.0245(9) 0.4866(5) 0.062(3) Uani 1 1 d . . . . .
C2A C 0.1330(11) 0.9394(8) 0.5299(4) 0.052(2) Uani 1 1 d . . . . .
H2A H 0.226391 0.899020 0.550688 0.062 Uiso 1 1 calc R U . . .
C3A C -0.0229(12) 0.9112(10) 0.5440(5) 0.068(3) Uani 1 1 d . . . . .
H3A H -0.038240 0.850651 0.573285 0.082 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.978(5) 3_576 ?
Cu1 N1 1.985(5) . ?
Cu1 Cl1 2.2642(16) . ?
Cu1 Cl2 2.2670(17) . ?
N4 C17 1.334(8) . ?
N4 C16 1.391(7) . ?
N2 C3 1.340(8) . ?
N2 C2 1.379(9) . ?
N2 C4 1.473(7) . ?
N1 C3 1.327(8) . ?
N1 C1 1.388(8) . ?
N3 C17 1.345(7) . ?
N3 C15 1.371(8) . ?
N3 C14 1.478(8) . ?
C3 H3 0.9500 . ?
C5 C6 1.408(8) . ?
C5 C12 1.409(8) . ?
C5 C4 1.519(8) . ?
C12 C11 1.374(8) . ?
C12 C13 1.514(8) . ?
C14 C8 1.518(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C7 C6 1.532(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C2 C1 1.350(10) . ?
C2 H2 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C17 H17 0.9500 . ?
C9 C8 1.400(9) . ?
C9 C11 1.400(8) . ?
C9 C10 1.509(9) . ?
C8 C6 1.401(8) . ?
C11 H11 0.9500 . ?
C16 C15 1.355(9) . ?
C16 H16 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1 H1 0.9500 . ?
C15 H15 0.9500 . ?
F1A C1A 1.387(10) . ?
C1A C3A 1.330(13) 3_576 ?
C1A C2A 1.351(13) . ?
C2A C3A 1.433(13) . ?
C2A H2A 0.9500 . ?
C3A H3A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 N1 160.6(2) 3_576 . ?
N4 Cu1 Cl1 92.25(15) 3_576 . ?
N1 Cu1 Cl1 92.92(15) . . ?
N4 Cu1 Cl2 93.10(15) 3_576 . ?
N1 Cu1 Cl2 90.95(15) . . ?
Cl1 Cu1 Cl2 152.31(8) . . ?
C17 N4 C16 105.0(5) . . ?
C17 N4 Cu1 128.4(4) . 3_576 ?
C16 N4 Cu1 126.6(4) . 3_576 ?
C3 N2 C2 107.5(5) . . ?
C3 N2 C4 126.4(5) . . ?
C2 N2 C4 126.0(5) . . ?
C3 N1 C1 105.7(5) . . ?
C3 N1 Cu1 128.4(4) . . ?
C1 N1 Cu1 125.6(4) . . ?
C17 N3 C15 107.4(5) . . ?
C17 N3 C14 127.3(5) . . ?
C15 N3 C14 125.2(5) . . ?
N1 C3 N2 111.1(5) . . ?
N1 C3 H3 124.5 . . ?
N2 C3 H3 124.5 . . ?
C6 C5 C12 119.4(5) . . ?
C6 C5 C4 120.4(5) . . ?
C12 C5 C4 120.1(5) . . ?
C11 C12 C5 119.3(5) . . ?
C11 C12 C13 118.7(5) . . ?
C5 C12 C13 122.0(6) . . ?
N3 C14 C8 111.1(5) . . ?
N3 C14 H14A 109.4 . . ?
C8 C14 H14A 109.4 . . ?
N3 C14 H14B 109.4 . . ?
C8 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C2 N2 106.4(6) . . ?
C1 C2 H2 126.8 . . ?
N2 C2 H2 126.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C4 C5 111.5(5) . . ?
N2 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N4 C17 N3 111.4(5) . . ?
N4 C17 H17 124.3 . . ?
N3 C17 H17 124.3 . . ?
C8 C9 C11 118.6(6) . . ?
C8 C9 C10 122.7(6) . . ?
C11 C9 C10 118.7(5) . . ?
C9 C8 C6 120.0(5) . . ?
C9 C8 C14 119.9(6) . . ?
C6 C8 C14 120.1(5) . . ?
C8 C6 C5 120.2(5) . . ?
C8 C6 C7 119.2(5) . . ?
C5 C6 C7 120.6(5) . . ?
C12 C11 C9 122.3(5) . . ?
C12 C11 H11 118.9 . . ?
C9 C11 H11 118.9 . . ?
C15 C16 N4 109.6(5) . . ?
C15 C16 H16 125.2 . . ?
N4 C16 H16 125.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C1 N1 109.3(6) . . ?
C2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?
C16 C15 N3 106.6(5) . . ?
C16 C15 H15 126.7 . . ?
N3 C15 H15 126.7 . . ?
C3A C1A C2A 125.6(9) 3_576 . ?
C3A C1A F1A 116.8(10) 3_576 . ?
C2A C1A F1A 117.4(9) . . ?
C1A C2A C3A 118.8(9) . . ?
C1A C2A H2A 120.6 . . ?
C3A C2A H2A 120.6 . . ?
C1A C3A C2A 115.6(10) 3_576 . ?
C1A C3A H3A 122.2 3_576 . ?
C2A C3A H3A 122.2 . . ?

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 0.4(7) . . . . ?
Cu1 N1 C3 N2 -172.9(4) . . . . ?
C2 N2 C3 N1 0.1(8) . . . . ?
C4 N2 C3 N1 178.3(5) . . . . ?
C6 C5 C12 C11 -1.2(9) . . . . ?
C4 C5 C12 C11 176.1(5) . . . . ?
C6 C5 C12 C13 177.5(6) . . . . ?
C4 C5 C12 C13 -5.2(9) . . . . ?
C17 N3 C14 C8 135.7(6) . . . . ?
C15 N3 C14 C8 -47.9(8) . . . . ?
C3 N2 C2 C1 -0.6(8) . . . . ?
C4 N2 C2 C1 -178.8(6) . . . . ?
C3 N2 C4 C5 -121.8(6) . . . . ?
C2 N2 C4 C5 56.1(8) . . . . ?
C6 C5 C4 N2 70.6(7) . . . . ?
C12 C5 C4 N2 -106.7(6) . . . . ?
C16 N4 C17 N3 -0.5(7) . . . . ?
Cu1 N4 C17 N3 177.4(4) 3_576 . . . ?
C15 N3 C17 N4 0.3(7) . . . . ?
C14 N3 C17 N4 177.3(5) . . . . ?
C11 C9 C8 C6 -0.7(9) . . . . ?
C10 C9 C8 C6 -179.8(5) . . . . ?
C11 C9 C8 C14 -179.4(5) . . . . ?
C10 C9 C8 C14 1.4(9) . . . . ?
N3 C14 C8 C9 100.7(7) . . . . ?
N3 C14 C8 C6 -78.0(7) . . . . ?
C9 C8 C6 C5 -2.7(9) . . . . ?
C14 C8 C6 C5 176.0(5) . . . . ?
C9 C8 C6 C7 176.4(6) . . . . ?
C14 C8 C6 C7 -4.8(8) . . . . ?
C12 C5 C6 C8 3.7(9) . . . . ?
C4 C5 C6 C8 -173.6(5) . . . . ?
C12 C5 C6 C7 -175.5(6) . . . . ?
C4 C5 C6 C7 7.2(9) . . . . ?
C5 C12 C11 C9 -2.3(9) . . . . ?
C13 C12 C11 C9 179.0(6) . . . . ?
C8 C9 C11 C12 3.2(9) . . . . ?
C10 C9 C11 C12 -177.6(6) . . . . ?
C17 N4 C16 C15 0.4(8) . . . . ?
Cu1 N4 C16 C15 -177.5(5) 3_576 . . . ?
N2 C2 C1 N1 0.8(9) . . . . ?
C3 N1 C1 C2 -0.8(8) . . . . ?
Cu1 N1 C1 C2 172.8(5) . . . . ?
N4 C16 C15 N3 -0.3(8) . . . . ?
C17 N3 C15 C16 0.0(7) . . . . ?
C14 N3 C15 C16 -177.1(6) . . . . ?
C3A C1A C2A C3A 1.9(17) 3_576 . . . ?
F1A C1A C2A C3A 177.7(8) . . . . ?
C1A C2A C3A C1A -1.7(16) . . . 3_576 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 Cl2 0.95 2.59 3.100(6) 113.9 .
C3 H3 Cl2 0.95 2.67 3.433(7) 138.1 3_566
C14 H14A Cl1 0.99 2.74 3.635(6) 151.3 4_576
C2 H2 F1A 0.95 2.42 3.086(10) 127.2 3_676
C4 H4B Cl2 0.99 2.74 3.579(7) 142.5 3_566
C16 H16 Cl2 0.95 2.65 3.149(7) 113.4 3_576
C15 H15 Cl1 0.95 2.94 3.746(7) 143.8 3_676

_refine_diff_density_max         1.018
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.126

####################################################################### 
# 
# 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 1569708'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            1
_chemical_melting_point          ?
_chemical_formula_moiety         
'	C35.09 H43.26 Cl4 Cu2 N8 O1.09, 0.912(C H3 O)'
_chemical_formula_sum            'C36 H46 Cl4 Cu2 N8 O2'
_chemical_formula_weight         891.69

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                   8.4261(10)
_cell_length_b                   10.7068(13)
_cell_length_c                   21.974(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.441(2)
_cell_angle_gamma                90
_cell_volume                     1955.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4118
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      28.08

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.405
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8385
_exptl_absorpt_correction_T_max  0.9331
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8066
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_max         28.081
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             4121
_reflns_number_gt                2999
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1216P)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         4121
_refine_ls_number_parameters     260
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1862
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.02110(6) 0.77241(5) 0.40002(2) 0.0210(2) Uani 1 1 d . . . . .
Cl1 Cl 0.15039(13) 0.80449(10) 0.31831(4) 0.0230(3) Uani 1 1 d . . . . .
Cl2 Cl -0.12415(14) 0.64463(11) 0.45434(5) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.2225(5) 0.7259(3) 0.45498(14) 0.0187(8) Uani 1 1 d . . . . .
C8 C 0.7617(6) 0.7417(4) 0.70212(17) 0.0188(9) Uani 1 1 d . . . . .
H8 H 0.874912 0.743735 0.715174 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6665(5) 0.8239(4) 0.72963(16) 0.0178(9) Uani 1 1 d . . . . .
C12 C 0.4319(5) 0.7331(4) 0.66586(17) 0.0170(9) Uani 1 1 d . . . . .
C5 C 0.5317(5) 0.6551(4) 0.63778(15) 0.0181(9) Uani 1 1 d . . . . .
N2 N 0.3962(4) 0.6435(3) 0.52985(13) 0.0175(7) Uani 1 1 d . . . . .
N4 N 0.1739(4) 1.1408(3) 0.64050(14) 0.0188(8) Uani 1 1 d . . . . .
C11 C 0.4997(5) 0.8181(4) 0.71149(15) 0.0174(9) Uani 1 1 d . . . . .
C2 C 0.4803(6) 0.7243(4) 0.49942(19) 0.0278(11) Uani 1 1 d . . . . .
H2 H 0.592176 0.742046 0.508498 0.033 Uiso 1 1 calc R U . . .
C6 C 0.6996(5) 0.6576(4) 0.65683(16) 0.0174(8) Uani 1 1 d . . . . .
N3 N 0.3329(4) 1.0078(3) 0.69635(14) 0.0191(8) Uani 1 1 d . . . . .
C10 C 0.7491(6) 0.9157(4) 0.77635(17) 0.0261(10) Uani 1 1 d . . . . .
H10A H 0.864459 0.897133 0.785078 0.039 Uiso 1 1 calc R U . . .
H10B H 0.703489 0.909019 0.814488 0.039 Uiso 1 1 calc R U . . .
H10C H 0.732956 1.000636 0.759888 0.039 Uiso 1 1 calc R U . . .
C4 C 0.4611(5) 0.5707(4) 0.58507(16) 0.0206(9) Uani 1 1 d . . . . .
H4A H 0.545367 0.513291 0.575221 0.025 Uiso 1 1 calc R U . . .
H4B H 0.374055 0.519665 0.597696 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2408(5) 0.6468(4) 0.50156(16) 0.0174(8) Uani 1 1 d . . . . .
H3 H 0.156475 0.598600 0.513639 0.021 Uiso 1 1 calc R U . . .
C1 C 0.3720(6) 0.7741(4) 0.45364(19) 0.0277(11) Uani 1 1 d . . . . .
H1 H 0.396391 0.834104 0.424680 0.033 Uiso 1 1 calc R U . . .
C7 C 0.8121(6) 0.5718(4) 0.63024(18) 0.0231(9) Uani 1 1 d . . . . .
H7A H 0.923234 0.589813 0.649226 0.035 Uiso 1 1 calc R U . . .
H7B H 0.800000 0.584811 0.585572 0.035 Uiso 1 1 calc R U . . .
H7C H 0.786254 0.484857 0.638606 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2510(6) 0.7287(4) 0.64732(18) 0.0228(9) Uani 1 1 d . . . . .
H13A H 0.216797 0.793356 0.616406 0.034 Uiso 1 1 calc R U . . .
H13B H 0.199968 0.743281 0.683672 0.034 Uiso 1 1 calc R U . . .
H13C H 0.219163 0.646424 0.629887 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3926(6) 0.9067(4) 0.73983(16) 0.0215(9) Uani 1 1 d . . . . .
H14A H 0.300239 0.860122 0.751122 0.026 Uiso 1 1 calc R U . . .
H14B H 0.453928 0.943306 0.777963 0.026 Uiso 1 1 calc R U . . .
C17 C 0.1822(5) 1.0473(4) 0.68003(16) 0.0194(9) Uani 1 1 d . . . . .
H17 H 0.092171 1.012674 0.694938 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4300(6) 1.0818(4) 0.66676(18) 0.0247(10) Uani 1 1 d . . . . .
H15 H 0.543619 1.077065 0.669976 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3297(6) 1.1626(4) 0.63212(18) 0.0267(10) Uani 1 1 d . . . . .
H16 H 0.362128 1.224959 0.605960 0.032 Uiso 1 1 calc R U . . .
O1A O -0.0488(9) 1.0278(6) 0.5449(3) 0.042(2) Uani 0.544(10) 1 d D . P A 1
C1A C -0.165(2) 0.9353(18) 0.5474(9) 0.060(6) Uani 0.544(10) 1 d D . P A 1
H1A1 H -0.130382 0.857224 0.530385 0.089 Uiso 0.544(10) 1 calc R U P A 1
H1A2 H -0.267708 0.961949 0.523104 0.089 Uiso 0.544(10) 1 calc R U P A 1
H1A3 H -0.178955 0.922063 0.590325 0.089 Uiso 0.544(10) 1 calc R U P A 1
O1B O 0.0500(11) 1.1260(8) 0.4419(3) 0.036(2) Uani 0.456(10) 1 d . . P A 2
C1B C 0.202(2) 1.0690(15) 0.4354(8) 0.034(4) Uani 0.456(10) 1 d . . P A 2
H1B1 H 0.270208 1.130515 0.418773 0.052 Uiso 0.456(10) 1 calc R U P A 2
H1B2 H 0.183323 0.997740 0.407106 0.052 Uiso 0.456(10) 1 calc R U P A 2
H1B3 H 0.256955 1.040235 0.475765 0.052 Uiso 0.456(10) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.968(4) 3_576 ?
Cu1 N1 1.979(4) . ?
Cu1 Cl1 2.2739(10) . ?
Cu1 Cl2 2.2964(11) . ?
N1 C3 1.318(5) . ?
N1 C1 1.366(6) . ?
C8 C6 1.381(6) . ?
C8 C9 1.393(6) . ?
C8 H8 0.9500 . ?
C9 C11 1.399(6) . ?
C9 C10 1.507(5) . ?
C12 C5 1.399(6) . ?
C12 C11 1.404(6) . ?
C12 C13 1.512(6) . ?
C5 C6 1.408(6) . ?
C5 C4 1.512(5) . ?
N2 C3 1.355(5) . ?
N2 C2 1.361(6) . ?
N2 C4 1.470(5) . ?
N4 C17 1.320(5) . ?
N4 C16 1.376(6) . ?
C11 C14 1.512(5) . ?
C2 C1 1.352(7) . ?
C2 H2 0.9500 . ?
C6 C7 1.505(6) . ?
N3 C17 1.330(5) . ?
N3 C15 1.376(5) . ?
N3 C14 1.476(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 H3 0.9500 . ?
C1 H1 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 H17 0.9500 . ?
C15 C16 1.353(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O1A C1A 1.401(9) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
O1B C1B 1.45(2) . ?
C1B H1B1 0.9800 . ?
C1B H1B2 0.9800 . ?
C1B H1B3 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 164.50(14) 3_576 . ?
N4 Cu1 Cl1 92.52(9) 3_576 . ?
N1 Cu1 Cl1 92.63(10) . . ?
N4 Cu1 Cl2 92.28(10) 3_576 . ?
N1 Cu1 Cl2 90.55(10) . . ?
Cl1 Cu1 Cl2 149.96(5) . . ?
C3 N1 C1 105.6(4) . . ?
C3 N1 Cu1 127.9(3) . . ?
C1 N1 Cu1 126.4(3) . . ?
C6 C8 C9 123.2(4) . . ?
C6 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C8 C9 C11 118.1(4) . . ?
C8 C9 C10 118.2(4) . . ?
C11 C9 C10 123.6(4) . . ?
C5 C12 C11 119.9(4) . . ?
C5 C12 C13 121.0(4) . . ?
C11 C12 C13 119.1(4) . . ?
C12 C5 C6 120.3(4) . . ?
C12 C5 C4 120.3(4) . . ?
C6 C5 C4 119.3(4) . . ?
C3 N2 C2 107.5(3) . . ?
C3 N2 C4 126.4(3) . . ?
C2 N2 C4 126.1(4) . . ?
C17 N4 C16 105.5(4) . . ?
C17 N4 Cu1 127.3(3) . 3_576 ?
C16 N4 Cu1 127.2(3) . 3_576 ?
C9 C11 C12 120.3(4) . . ?
C9 C11 C14 119.6(4) . . ?
C12 C11 C14 120.1(4) . . ?
C1 C2 N2 105.9(4) . . ?
C1 C2 H2 127.1 . . ?
N2 C2 H2 127.1 . . ?
C8 C6 C5 118.1(4) . . ?
C8 C6 C7 119.3(4) . . ?
C5 C6 C7 122.6(4) . . ?
C17 N3 C15 107.7(3) . . ?
C17 N3 C14 128.1(4) . . ?
C15 N3 C14 124.2(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C4 C5 111.2(3) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N1 C3 N2 110.7(4) . . ?
N1 C3 H3 124.7 . . ?
N2 C3 H3 124.7 . . ?
C2 C1 N1 110.3(4) . . ?
C2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C11 110.9(3) . . ?
N3 C14 H14A 109.5 . . ?
C11 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
N4 C17 N3 111.4(4) . . ?
N4 C17 H17 124.3 . . ?
N3 C17 H17 124.3 . . ?
C16 C15 N3 105.6(4) . . ?
C16 C15 H15 127.2 . . ?
N3 C15 H15 127.2 . . ?
C15 C16 N4 109.8(4) . . ?
C15 C16 H16 125.1 . . ?
N4 C16 H16 125.1 . . ?
O1A C1A H1A1 109.5 . . ?
O1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
O1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
O1B C1B H1B1 109.5 . . ?
O1B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
O1B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 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
C6 C8 C9 C11 1.8(6) . . . . ?
C6 C8 C9 C10 -177.1(3) . . . . ?
C11 C12 C5 C6 2.6(5) . . . . ?
C13 C12 C5 C6 -178.0(3) . . . . ?
C11 C12 C5 C4 -175.1(3) . . . . ?
C13 C12 C5 C4 4.3(5) . . . . ?
C8 C9 C11 C12 -1.3(5) . . . . ?
C10 C9 C11 C12 177.5(3) . . . . ?
C8 C9 C11 C14 -179.3(3) . . . . ?
C10 C9 C11 C14 -0.5(5) . . . . ?
C5 C12 C11 C9 -0.8(5) . . . . ?
C13 C12 C11 C9 179.8(3) . . . . ?
C5 C12 C11 C14 177.2(3) . . . . ?
C13 C12 C11 C14 -2.2(5) . . . . ?
C3 N2 C2 C1 0.2(5) . . . . ?
C4 N2 C2 C1 -177.2(4) . . . . ?
C9 C8 C6 C5 -0.1(6) . . . . ?
C9 C8 C6 C7 -179.5(3) . . . . ?
C12 C5 C6 C8 -2.2(5) . . . . ?
C4 C5 C6 C8 175.5(3) . . . . ?
C12 C5 C6 C7 177.3(4) . . . . ?
C4 C5 C6 C7 -5.1(5) . . . . ?
C3 N2 C4 C5 -117.9(4) . . . . ?
C2 N2 C4 C5 59.0(5) . . . . ?
C12 C5 C4 N2 67.7(5) . . . . ?
C6 C5 C4 N2 -110.0(4) . . . . ?
C1 N1 C3 N2 0.2(4) . . . . ?
Cu1 N1 C3 N2 -177.4(2) . . . . ?
C2 N2 C3 N1 -0.2(4) . . . . ?
C4 N2 C3 N1 177.1(3) . . . . ?
N2 C2 C1 N1 -0.1(5) . . . . ?
C3 N1 C1 C2 -0.1(5) . . . . ?
Cu1 N1 C1 C2 177.5(3) . . . . ?
C17 N3 C14 C11 130.3(4) . . . . ?
C15 N3 C14 C11 -52.1(5) . . . . ?
C9 C11 C14 N3 103.9(4) . . . . ?
C12 C11 C14 N3 -74.1(5) . . . . ?
C16 N4 C17 N3 -0.9(4) . . . . ?
Cu1 N4 C17 N3 177.4(2) 3_576 . . . ?
C15 N3 C17 N4 1.4(5) . . . . ?
C14 N3 C17 N4 179.3(3) . . . . ?
C17 N3 C15 C16 -1.3(5) . . . . ?
C14 N3 C15 C16 -179.3(3) . . . . ?
N3 C15 C16 N4 0.8(5) . . . . ?
C17 N4 C16 C15 0.0(5) . . . . ?
Cu1 N4 C16 C15 -178.3(3) 3_576 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4B Cl2 0.99 2.84 3.650(5) 139.9 3_566
C3 H3 Cl2 0.95 2.55 3.080(4) 115.1 .
C3 H3 Cl2 0.95 2.72 3.457(4) 134.6 3_566
C14 H14A Cl1 0.99 2.74 3.662(4) 155.7 4_576
C15 H15 Cl1 0.95 2.85 3.703(5) 150.5 3_676
C16 H16 Cl2 0.95 2.62 3.129(5) 114.1 3_576
C1A H1A1 Cl2 0.98 2.83 3.771(17) 161.3 .
C1B H1B2 Cl1 0.98 2.83 3.802(17) 174.0 .

_refine_diff_density_max         1.033
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.148

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1569714'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            5
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, C S2'
_chemical_formula_sum            'C35 H40 Cl4 Cu2 N8 S2'
_chemical_formula_weight         905.77

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.3483(11)
_cell_length_b                   10.5979(14)
_cell_length_c                   22.200(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.700(2)
_cell_angle_gamma                90
_cell_volume                     1941.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3309
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      24.82

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    1.516
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7934
_exptl_absorpt_correction_T_max  0.9105
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8911
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.856
_diffrn_reflns_theta_max         24.824
_diffrn_reflns_theta_full        24.824
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3309
_reflns_number_gt                2750
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+1.9868P] 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         3309
_refine_ls_number_parameters     247
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0726
_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
Cu1 Cu 0.48022(4) 0.23191(3) 0.10205(2) 0.01506(11) Uani 1 1 d . . . . .
Cl2 Cl 0.34409(8) 0.19286(7) 0.18133(3) 0.01928(17) Uani 1 1 d . . . . .
Cl1 Cl 0.62267(8) 0.36800(7) 0.05167(3) 0.02221(18) Uani 1 1 d . . . . .
N1 N 0.2795(3) 0.2603(2) 0.04418(10) 0.0169(5) Uani 1 1 d . . . . .
N4 N 0.3244(3) -0.1426(2) -0.14113(11) 0.0167(5) Uani 1 1 d . . . . .
N3 N 0.1638(3) -0.0100(2) -0.19723(10) 0.0157(5) Uani 1 1 d . . . . .
N2 N 0.1018(3) 0.3400(2) -0.02934(10) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.0264(4) 0.2430(3) -0.00369(13) 0.0250(7) Uani 1 1 d . . . . .
H2 H -0.082154 0.215452 -0.015350 0.030 Uiso 1 1 calc R U . . .
C6 C -0.2081(3) 0.3368(3) -0.15455(12) 0.0163(6) Uani 1 1 d . . . . .
C8 C -0.2699(3) 0.2545(3) -0.20113(12) 0.0178(6) Uani 1 1 d . . . . .
H8 H -0.383631 0.252913 -0.214088 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2536(3) 0.3475(3) 0.00031(13) 0.0176(6) Uani 1 1 d . . . . .
H3 H 0.332146 0.406792 -0.008618 0.021 Uiso 1 1 calc R U . . .
C5 C -0.0398(3) 0.3385(3) -0.13562(12) 0.0162(6) Uani 1 1 d . . . . .
C11 C -0.0048(3) 0.1798(3) -0.21191(12) 0.0163(6) Uani 1 1 d . . . . .
C9 C -0.1728(3) 0.1744(3) -0.22955(12) 0.0158(6) Uani 1 1 d . . . . .
C12 C 0.0621(3) 0.2630(3) -0.16535(12) 0.0154(6) Uani 1 1 d . . . . .
C4 C 0.0307(3) 0.4193(3) -0.08159(12) 0.0182(6) Uani 1 1 d . . . . .
H4A H 0.115480 0.475249 -0.093595 0.022 Uiso 1 1 calc R U . . .
H4B H -0.055613 0.473154 -0.069238 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3167(3) -0.0499(3) -0.18202(12) 0.0155(6) Uani 1 1 d . . . . .
H17 H 0.407132 -0.016690 -0.198105 0.019 Uiso 1 1 calc R U . . .
C13 C 0.2443(3) 0.2672(3) -0.14641(13) 0.0197(6) Uani 1 1 d . . . . .
H13A H 0.275640 0.350119 -0.128902 0.030 Uiso 1 1 calc R U . . .
H13B H 0.297976 0.252814 -0.182127 0.030 Uiso 1 1 calc R U . . .
H13C H 0.277020 0.201540 -0.115964 0.030 Uiso 1 1 calc R U . . .
C10 C -0.2520(4) 0.0830(3) -0.27739(13) 0.0209(7) Uani 1 1 d . . . . .
H10A H -0.369530 0.096412 -0.283986 0.031 Uiso 1 1 calc R U . . .
H10B H -0.228258 -0.003702 -0.263513 0.031 Uiso 1 1 calc R U . . .
H10C H -0.209592 0.097148 -0.315654 0.031 Uiso 1 1 calc R U . . .
C15 C 0.0684(3) -0.0808(3) -0.16482(13) 0.0195(6) Uani 1 1 d . . . . .
H15 H -0.045655 -0.074192 -0.166379 0.023 Uiso 1 1 calc R U . . .
C16 C 0.1683(3) -0.1616(3) -0.13035(13) 0.0188(6) Uani 1 1 d . . . . .
H16 H 0.135907 -0.221983 -0.102965 0.023 Uiso 1 1 calc R U . . .
C14 C 0.1041(3) 0.0909(3) -0.24095(12) 0.0183(6) Uani 1 1 d . . . . .
H14A H 0.042726 0.053311 -0.278286 0.022 Uiso 1 1 calc R U . . .
H14B H 0.196947 0.138345 -0.252563 0.022 Uiso 1 1 calc R U . . .
C7 C -0.3228(3) 0.4218(3) -0.12651(14) 0.0240(7) Uani 1 1 d . . . . .
H7A H -0.317652 0.401177 -0.083231 0.036 Uiso 1 1 calc R U . . .
H7B H -0.433656 0.409082 -0.147473 0.036 Uiso 1 1 calc R U . . .
H7C H -0.291405 0.510092 -0.130707 0.036 Uiso 1 1 calc R U . . .
C1 C 0.1365(4) 0.1941(3) 0.04147(14) 0.0252(7) Uani 1 1 d . . . . .
H1 H 0.118041 0.125408 0.067050 0.030 Uiso 1 1 calc R U . . .
S1A S 0.4472(8) -0.0519(6) 0.0306(3) 0.0581(11) Uani 0.5 1 d D . P A -1
S2A S 0.6102(3) 0.0949(2) -0.06286(12) 0.0599(8) Uani 0.5 1 d D . P A -1
C1A C 0.535(3) 0.018(2) -0.0154(10) 0.058(6) Uani 0.5 1 d D . 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 1.970(2) 3_655 ?
Cu1 N1 1.974(2) . ?
Cu1 Cl1 2.2687(8) . ?
Cu1 Cl2 2.2728(8) . ?
N1 C3 1.336(4) . ?
N1 C1 1.378(4) . ?
N4 C17 1.333(4) . ?
N4 C16 1.375(4) . ?
N3 C17 1.338(4) . ?
N3 C15 1.374(4) . ?
N3 C14 1.480(4) . ?
N2 C3 1.339(4) . ?
N2 C2 1.373(4) . ?
N2 C4 1.482(4) . ?
C2 C1 1.356(4) . ?
C2 H2 0.9500 . ?
C6 C8 1.391(4) . ?
C6 C5 1.404(4) . ?
C6 C7 1.515(4) . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
C3 H3 0.9500 . ?
C5 C12 1.404(4) . ?
C5 C4 1.518(4) . ?
C11 C9 1.399(4) . ?
C11 C12 1.408(4) . ?
C11 C14 1.519(4) . ?
C9 C10 1.514(4) . ?
C12 C13 1.516(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C17 H17 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C15 C16 1.349(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C1 H1 0.9500 . ?
S1A C1A 1.537(2) . ?
S2A C1A 1.537(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 N1 157.61(10) 3_655 . ?
N4 Cu1 Cl1 93.53(7) 3_655 . ?
N1 Cu1 Cl1 92.23(7) . . ?
N4 Cu1 Cl2 92.82(7) 3_655 . ?
N1 Cu1 Cl2 93.27(7) . . ?
Cl1 Cu1 Cl2 149.12(3) . . ?
C3 N1 C1 106.1(2) . . ?
C3 N1 Cu1 127.4(2) . . ?
C1 N1 Cu1 126.5(2) . . ?
C17 N4 C16 106.1(2) . . ?
C17 N4 Cu1 127.25(19) . 3_655 ?
C16 N4 Cu1 126.64(19) . 3_655 ?
C17 N3 C15 107.6(2) . . ?
C17 N3 C14 127.4(2) . . ?
C15 N3 C14 125.0(2) . . ?
C3 N2 C2 107.5(2) . . ?
C3 N2 C4 126.0(2) . . ?
C2 N2 C4 126.5(2) . . ?
C1 C2 N2 106.9(3) . . ?
C1 C2 H2 126.6 . . ?
N2 C2 H2 126.6 . . ?
C8 C6 C5 118.2(3) . . ?
C8 C6 C7 119.5(2) . . ?
C5 C6 C7 122.4(3) . . ?
C9 C8 C6 123.0(3) . . ?
C9 C8 H8 118.5 . . ?
C6 C8 H8 118.5 . . ?
N1 C3 N2 110.7(3) . . ?
N1 C3 H3 124.7 . . ?
N2 C3 H3 124.7 . . ?
C12 C5 C6 120.1(3) . . ?
C12 C5 C4 120.2(2) . . ?
C6 C5 C4 119.6(3) . . ?
C9 C11 C12 120.0(3) . . ?
C9 C11 C14 119.7(3) . . ?
C12 C11 C14 120.2(2) . . ?
C8 C9 C11 118.5(3) . . ?
C8 C9 C10 119.1(2) . . ?
C11 C9 C10 122.4(3) . . ?
C5 C12 C11 120.1(2) . . ?
C5 C12 C13 120.4(2) . . ?
C11 C12 C13 119.5(3) . . ?
N2 C4 C5 111.1(2) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N4 C17 N3 110.5(2) . . ?
N4 C17 H17 124.7 . . ?
N3 C17 H17 124.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C15 N3 106.6(2) . . ?
C16 C15 H15 126.7 . . ?
N3 C15 H15 126.7 . . ?
C15 C16 N4 109.2(3) . . ?
C15 C16 H16 125.4 . . ?
N4 C16 H16 125.4 . . ?
N3 C14 C11 109.5(2) . . ?
N3 C14 H14A 109.8 . . ?
C11 C14 H14A 109.8 . . ?
N3 C14 H14B 109.8 . . ?
C11 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C1 N1 108.9(3) . . ?
C2 C1 H1 125.6 . . ?
N1 C1 H1 125.6 . . ?
S2A C1A S1A 175.2(18) . . ?

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 0.1(3) . . . . ?
C4 N2 C2 C1 178.2(3) . . . . ?
C5 C6 C8 C9 0.0(4) . . . . ?
C7 C6 C8 C9 179.4(3) . . . . ?
C1 N1 C3 N2 0.5(3) . . . . ?
Cu1 N1 C3 N2 -178.98(18) . . . . ?
C2 N2 C3 N1 -0.3(3) . . . . ?
C4 N2 C3 N1 -178.5(2) . . . . ?
C8 C6 C5 C12 3.0(4) . . . . ?
C7 C6 C5 C12 -176.5(3) . . . . ?
C8 C6 C5 C4 -175.1(3) . . . . ?
C7 C6 C5 C4 5.5(4) . . . . ?
C6 C8 C9 C11 -2.2(4) . . . . ?
C6 C8 C9 C10 176.6(3) . . . . ?
C12 C11 C9 C8 1.4(4) . . . . ?
C14 C11 C9 C8 178.3(3) . . . . ?
C12 C11 C9 C10 -177.3(3) . . . . ?
C14 C11 C9 C10 -0.4(4) . . . . ?
C6 C5 C12 C11 -3.6(4) . . . . ?
C4 C5 C12 C11 174.4(3) . . . . ?
C6 C5 C12 C13 178.2(3) . . . . ?
C4 C5 C12 C13 -3.8(4) . . . . ?
C9 C11 C12 C5 1.4(4) . . . . ?
C14 C11 C12 C5 -175.5(3) . . . . ?
C9 C11 C12 C13 179.6(3) . . . . ?
C14 C11 C12 C13 2.7(4) . . . . ?
C3 N2 C4 C5 125.2(3) . . . . ?
C2 N2 C4 C5 -52.6(4) . . . . ?
C12 C5 C4 N2 -65.3(3) . . . . ?
C6 C5 C4 N2 112.7(3) . . . . ?
C16 N4 C17 N3 0.0(3) . . . . ?
Cu1 N4 C17 N3 -178.41(18) 3_655 . . . ?
C15 N3 C17 N4 -0.3(3) . . . . ?
C14 N3 C17 N4 -180.0(3) . . . . ?
C17 N3 C15 C16 0.4(3) . . . . ?
C14 N3 C15 C16 -179.9(3) . . . . ?
N3 C15 C16 N4 -0.4(3) . . . . ?
C17 N4 C16 C15 0.2(3) . . . . ?
Cu1 N4 C16 C15 178.7(2) 3_655 . . . ?
C17 N3 C14 C11 -131.4(3) . . . . ?
C15 N3 C14 C11 49.0(4) . . . . ?
C9 C11 C14 N3 -105.1(3) . . . . ?
C12 C11 C14 N3 71.8(3) . . . . ?
N2 C2 C1 N1 0.2(4) . . . . ?
C3 N1 C1 C2 -0.4(3) . . . . ?
Cu1 N1 C1 C2 179.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 S2A 0.95 2.92 3.857(4) 169.7 1_455
C3 H3 Cl1 0.95 2.62 3.127(3) 113.9 .
C3 H3 Cl1 0.95 2.62 3.442(3) 145.1 3_665
C4 H4A Cl1 0.99 2.79 3.649(3) 145.3 3_665
C15 H15 Cl2 0.95 2.77 3.608(3) 148.3 3
C16 H16 Cl1 0.95 2.66 3.156(3) 113.3 3_655
C14 H14B Cl2 0.99 2.72 3.645(3) 155.4 4_565

_refine_diff_density_max         0.595
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.073

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1569712'
_audit_update_record             
;
2017-09-15 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT413_3                   
;
PROBLEM: Short Inter XH3 .. XHn     H1A3   ..  H16     ..       1.80 Ang.
RESPONSE: This A-alert arises from the acetone disorder
;
# Added during the CSD deposition process: Friday 15 September 2017 01:05 PM
# end Validation Reply Form

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            3
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, 1.02(C3 H6 O)'
_chemical_formula_sum            'C37.06 H46.12 Cl4 Cu2 N8 O1.02'
_chemical_formula_weight         888.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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.
The authors acknowledge the presence of an A-alert. Th short H1A3-H16
distance detecteed is due to the disordered acetone guest.
;

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                   8.386(3)
_cell_length_b                   10.778(4)
_cell_length_c                   22.282(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.205(4)
_cell_angle_gamma                90
_cell_volume                     1988.0(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4167
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      27.57

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             917
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.380
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10354
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.852
_diffrn_reflns_theta_max         27.570
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4168
_reflns_number_gt                2080
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0716P)²+2.1815P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0021(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4168
_refine_ls_number_parameters     234
_refine_ls_number_restraints     175
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1793
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.004
_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 -0.02000(9) 0.25724(8) 0.60421(3) 0.0401(3) Uani 1 1 d . U . . .
Cl2 Cl 0.1236(2) 0.13259(17) 0.55072(8) 0.0529(5) Uani 1 1 d . U . . .
Cl1 Cl -0.1526(2) 0.29457(17) 0.68324(7) 0.0492(5) Uani 1 1 d . U . . .
N2 N 0.3347(6) 0.4824(5) 0.6977(2) 0.0384(13) Uani 1 1 d . U . . .
N1 N 0.1746(6) 0.3469(5) 0.6434(2) 0.0408(13) Uani 1 1 d . U . . .
C5 C 0.5006(7) 0.6724(6) 0.7104(3) 0.0369(15) Uani 1 1 d . U . . .
C3 C 0.1823(7) 0.4416(6) 0.6818(3) 0.0371(15) Uani 1 1 d . U . . .
H3 H 0.091490 0.476213 0.696284 0.044 Uiso 1 1 calc R U . . .
N3 N 0.3956(6) 0.8465(6) 0.5296(2) 0.0554(8) Uani 1 1 d . U . . .
C4 C 0.3939(8) 0.5848(6) 0.7390(3) 0.0400(15) Uani 1 1 d . U . . .
H4A H 0.455568 0.550384 0.776960 0.048 Uiso 1 1 calc R U . . .
H4B H 0.300619 0.631302 0.749760 0.048 Uiso 1 1 calc R U . . .
C10 C 0.7012(7) 0.8312(6) 0.6553(3) 0.0360(15) Uani 1 1 d . U . . .
C13 C 0.6710(8) 0.6658(6) 0.7276(3) 0.0391(15) Uani 1 1 d . U . . .
C8 C 0.5327(7) 0.8321(6) 0.6369(3) 0.0387(15) Uani 1 1 d . U . . .
N4 N 0.2216(6) 0.7748(6) 0.4529(2) 0.0554(8) Uani 1 1 d . U . . .
C7 C 0.2507(7) 0.7601(6) 0.6460(3) 0.0414(15) Uani 1 1 d . U . . .
H7A H 0.217387 0.696940 0.614905 0.062 Uiso 1 1 calc R U . . .
H7B H 0.219282 0.842360 0.629513 0.062 Uiso 1 1 calc R U . . .
H7C H 0.197929 0.744043 0.681462 0.062 Uiso 1 1 calc R U . . .
C15 C 0.4616(8) 0.9183(6) 0.5844(3) 0.0467(17) Uani 1 1 d . U . . .
H15A H 0.374734 0.969463 0.597066 0.056 Uiso 1 1 calc R U . . .
H15B H 0.546925 0.974982 0.574726 0.056 Uiso 1 1 calc R U . . .
C11 C 0.8170(8) 0.9155(7) 0.6287(3) 0.0526(18) Uani 1 1 d . U . . .
H11A H 0.927001 0.902560 0.650321 0.079 Uiso 1 1 calc R U . . .
H11B H 0.785625 1.002182 0.633008 0.079 Uiso 1 1 calc R U . . .
H11C H 0.813227 0.896071 0.585488 0.079 Uiso 1 1 calc R U . . .
C6 C 0.4324(7) 0.7553(6) 0.6650(2) 0.0347(13) Uani 1 1 d . U . . .
C18 C 0.2438(8) 0.8502(7) 0.5004(3) 0.0554(8) Uani 1 1 d . U . . .
H18 H 0.161477 0.900827 0.512353 0.066 Uiso 1 1 calc R U . . .
C12 C 0.7648(8) 0.7479(6) 0.7006(3) 0.0415(15) Uani 1 1 d . U . . .
H12 H 0.878293 0.747386 0.713620 0.050 Uiso 1 1 calc R U . . .
C14 C 0.7511(8) 0.5745(6) 0.7749(3) 0.0490(18) Uani 1 1 d . U . . .
H14A H 0.867874 0.589543 0.782528 0.074 Uiso 1 1 calc R U . . .
H14B H 0.730207 0.489641 0.759844 0.074 Uiso 1 1 calc R U . . .
H14C H 0.707121 0.585349 0.812691 0.074 Uiso 1 1 calc R U . . .
C1 C 0.3318(8) 0.3252(7) 0.6354(3) 0.0531(19) Uani 1 1 d . U . . .
H1 H 0.365309 0.262447 0.610123 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4309(9) 0.4068(7) 0.6689(3) 0.0533(19) Uani 1 1 d . U . . .
H2 H 0.545085 0.411106 0.671962 0.064 Uiso 1 1 calc R U . . .
C16 C 0.4773(8) 0.7631(7) 0.5000(3) 0.0554(8) Uani 1 1 d . U . . .
H16 H 0.587563 0.739821 0.510445 0.066 Uiso 1 1 calc R U . . .
C17 C 0.3688(8) 0.7197(7) 0.4525(3) 0.0554(8) Uani 1 1 d . U . . .
H17 H 0.391763 0.660433 0.423478 0.066 Uiso 1 1 calc R U . . .
O1A O 0.2758(15) 0.5260(12) 0.5383(5) 0.109(5) Uani 0.51 1 d D U P A -1
C3A C -0.0127(15) 0.523(5) 0.5153(15) 0.23(2) Uani 0.51 1 d D U P A -1
H3A1 H -0.095874 0.494620 0.482143 0.348 Uiso 0.51 1 calc R U P A -1
H3A2 H -0.025601 0.479123 0.552863 0.348 Uiso 0.51 1 calc R U P A -1
H3A3 H -0.023760 0.612249 0.521172 0.348 Uiso 0.51 1 calc R U P A -1
C2A C 0.1548(14) 0.4949(15) 0.4995(6) 0.126(9) Uani 0.51 1 d D U P A -1
C1A C 0.190(3) 0.4328(18) 0.4411(6) 0.153(12) Uani 0.51 1 d D U P A -1
H1A1 H 0.087745 0.413090 0.414840 0.229 Uiso 0.51 1 calc R U P A -1
H1A2 H 0.253062 0.489336 0.419706 0.229 Uiso 0.51 1 calc R U P A -1
H1A3 H 0.251191 0.356223 0.451408 0.229 Uiso 0.51 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 1.976(5) . ?
Cu1 N4 1.977(5) 3_566 ?
Cu1 Cl1 2.2640(18) . ?
Cu1 Cl2 2.2660(19) . ?
N2 C3 1.344(7) . ?
N2 C2 1.376(8) . ?
N2 C4 1.472(7) . ?
N1 C3 1.327(8) . ?
N1 C1 1.378(8) . ?
C5 C6 1.402(8) . ?
C5 C13 1.420(8) . ?
C5 C4 1.510(8) . ?
C3 H3 0.9500 . ?
N3 C18 1.334(8) . ?
N3 C16 1.363(9) . ?
N3 C15 1.476(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C10 C12 1.392(8) . ?
C10 C8 1.407(8) . ?
C10 C11 1.518(9) . ?
C13 C12 1.384(9) . ?
C13 C14 1.517(8) . ?
C8 C6 1.397(8) . ?
C8 C15 1.538(8) . ?
N4 C18 1.325(8) . ?
N4 C17 1.371(8) . ?
C7 C6 1.516(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C18 H18 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1 C2 1.350(9) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C16 C17 1.364(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O1A C2A 1.2685(19) . ?
C3A C2A 1.5323(18) . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
C2A C1A 1.5323(18) . ?
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 Cu1 N4 158.5(2) . 3_566 ?
N1 Cu1 Cl1 92.50(15) . . ?
N4 Cu1 Cl1 93.19(16) 3_566 . ?
N1 Cu1 Cl2 92.93(16) . . ?
N4 Cu1 Cl2 91.70(17) 3_566 . ?
Cl1 Cu1 Cl2 152.00(8) . . ?
C3 N2 C2 106.7(5) . . ?
C3 N2 C4 128.4(5) . . ?
C2 N2 C4 124.9(5) . . ?
C3 N1 C1 105.4(5) . . ?
C3 N1 Cu1 127.8(4) . . ?
C1 N1 Cu1 126.8(4) . . ?
C6 C5 C13 120.2(6) . . ?
C6 C5 C4 120.1(6) . . ?
C13 C5 C4 119.6(5) . . ?
N1 C3 N2 111.6(5) . . ?
N1 C3 H3 124.2 . . ?
N2 C3 H3 124.2 . . ?
C18 N3 C16 107.4(6) . . ?
C18 N3 C15 126.1(6) . . ?
C16 N3 C15 126.5(5) . . ?
N2 C4 C5 111.6(5) . . ?
N2 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C12 C10 C8 117.7(6) . . ?
C12 C10 C11 118.3(6) . . ?
C8 C10 C11 123.9(6) . . ?
C12 C13 C5 117.9(6) . . ?
C12 C13 C14 119.8(6) . . ?
C5 C13 C14 122.3(6) . . ?
C6 C8 C10 120.9(6) . . ?
C6 C8 C15 120.7(5) . . ?
C10 C8 C15 118.3(6) . . ?
C18 N4 C17 105.1(6) . . ?
C18 N4 Cu1 128.2(5) . 3_566 ?
C17 N4 Cu1 126.8(5) . 3_566 ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C15 C8 111.1(6) . . ?
N3 C15 H15A 109.4 . . ?
C8 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
C8 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C6 C5 119.7(5) . . ?
C8 C6 C7 120.4(5) . . ?
C5 C6 C7 119.9(6) . . ?
N4 C18 N3 111.8(6) . . ?
N4 C18 H18 124.1 . . ?
N3 C18 H18 124.1 . . ?
C13 C12 C10 123.3(6) . . ?
C13 C12 H12 118.3 . . ?
C10 C12 H12 118.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C1 N1 109.6(6) . . ?
C2 C1 H1 125.2 . . ?
N1 C1 H1 125.2 . . ?
C1 C2 N2 106.8(6) . . ?
C1 C2 H2 126.6 . . ?
N2 C2 H2 126.6 . . ?
N3 C16 C17 106.1(6) . . ?
N3 C16 H16 127.0 . . ?
C17 C16 H16 127.0 . . ?
C16 C17 N4 109.6(6) . . ?
C16 C17 H17 125.2 . . ?
N4 C17 H17 125.2 . . ?
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 116.95(18) . . ?
O1A C2A C3A 116.97(18) . . ?
C1A C2A C3A 126.08(18) . . ?
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
C1 N1 C3 N2 1.1(7) . . . . ?
Cu1 N1 C3 N2 -177.8(4) . . . . ?
C2 N2 C3 N1 -1.7(7) . . . . ?
C4 N2 C3 N1 179.9(5) . . . . ?
C3 N2 C4 C5 -129.9(6) . . . . ?
C2 N2 C4 C5 52.1(8) . . . . ?
C6 C5 C4 N2 74.4(7) . . . . ?
C13 C5 C4 N2 -102.4(6) . . . . ?
C6 C5 C13 C12 3.5(9) . . . . ?
C4 C5 C13 C12 -179.8(5) . . . . ?
C6 C5 C13 C14 -177.7(6) . . . . ?
C4 C5 C13 C14 -0.9(9) . . . . ?
C12 C10 C8 C6 2.5(9) . . . . ?
C11 C10 C8 C6 -177.5(6) . . . . ?
C12 C10 C8 C15 -176.6(6) . . . . ?
C11 C10 C8 C15 3.5(9) . . . . ?
C18 N3 C15 C8 122.0(8) . . . . ?
C16 N3 C15 C8 -56.9(9) . . . . ?
C6 C8 C15 N3 -68.2(8) . . . . ?
C10 C8 C15 N3 110.9(6) . . . . ?
C10 C8 C6 C5 -2.6(9) . . . . ?
C15 C8 C6 C5 176.4(6) . . . . ?
C10 C8 C6 C7 178.1(6) . . . . ?
C15 C8 C6 C7 -2.9(9) . . . . ?
C13 C5 C6 C8 -0.4(9) . . . . ?
C4 C5 C6 C8 -177.2(5) . . . . ?
C13 C5 C6 C7 178.9(5) . . . . ?
C4 C5 C6 C7 2.1(8) . . . . ?
C17 N4 C18 N3 0.4(9) . . . . ?
Cu1 N4 C18 N3 178.6(5) 3_566 . . . ?
C16 N3 C18 N4 -0.7(9) . . . . ?
C15 N3 C18 N4 -179.8(6) . . . . ?
C5 C13 C12 C10 -3.7(9) . . . . ?
C14 C13 C12 C10 177.5(6) . . . . ?
C8 C10 C12 C13 0.8(9) . . . . ?
C11 C10 C12 C13 -179.3(6) . . . . ?
C3 N1 C1 C2 -0.1(8) . . . . ?
Cu1 N1 C1 C2 178.8(5) . . . . ?
N1 C1 C2 N2 -1.0(8) . . . . ?
C3 N2 C2 C1 1.6(8) . . . . ?
C4 N2 C2 C1 -180.0(6) . . . . ?
C18 N3 C16 C17 0.7(8) . . . . ?
C15 N3 C16 C17 179.8(7) . . . . ?
N3 C16 C17 N4 -0.5(9) . . . . ?
C18 N4 C17 C16 0.1(9) . . . . ?
Cu1 N4 C17 C16 -178.2(5) 3_566 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4B Cl1 0.99 2.73 3.651(7) 154.7 2_556
C15 H15A Cl2 0.99 2.81 3.640(7) 141.8 1_565
C18 H18 Cl2 0.95 2.68 3.449(8) 138.9 1_565
C18 H18 Cl2 0.95 2.60 3.115(7) 114.6 3_566
C1 H1 Cl2 0.95 2.64 3.140(7) 113.5 .
C2 H2 Cl1 0.95 2.80 3.661(7) 150.5 1_655

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.099

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1569713'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            4
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, C2 H3 N'
_chemical_formula_sum            'C36 H43 Cl4 Cu2 N9'
_chemical_formula_weight         870.67

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

_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                   8.325(5)
_cell_length_b                   10.568(6)
_cell_length_c                   22.158(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.506(7)
_cell_angle_gamma                90
_cell_volume                     1928.0(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1922
_cell_measurement_theta_min      2.4735
_cell_measurement_theta_max      26.4375

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    1.420
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_T_max  0.8687
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9199
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4432
_reflns_number_gt                3130
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+1.4895P] 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         4432
_refine_ls_number_parameters     234
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.02576(5) 0.26882(4) 0.39885(2) 0.02018(12) Uani 1 1 d . . . . .
Cl1 Cl 0.16197(9) 0.30939(9) 0.32056(4) 0.0244(2) Uani 1 1 d . . . . .
Cl2 Cl -0.11808(10) 0.13136(9) 0.44809(4) 0.0337(2) Uani 1 1 d . . . . .
N1 N 0.2273(3) 0.2392(3) 0.45655(12) 0.0240(6) Uani 1 1 d . . . . .
N4 N 0.1696(3) 0.6401(2) 0.63932(11) 0.0172(6) Uani 1 1 d . . . . .
C5 C 0.5405(4) 0.1590(3) 0.63656(13) 0.0176(7) Uani 1 1 d . . . . .
C4 C 0.4725(4) 0.0789(3) 0.58228(14) 0.0237(8) Uani 1 1 d . . . . .
H4A H 0.559853 0.025035 0.570296 0.028 Uiso 1 1 calc R U . . .
H4B H 0.386795 0.022616 0.593703 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7695(4) 0.2436(3) 0.70303(14) 0.0186(7) Uani 1 1 d . . . . .
H11 H 0.883114 0.244682 0.716849 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5026(4) 0.3188(3) 0.71198(13) 0.0160(6) Uani 1 1 d . . . . .
N3 N 0.3311(3) 0.5078(3) 0.69594(12) 0.0187(6) Uani 1 1 d . . . . .
C6 C 0.4370(4) 0.2356(3) 0.66550(13) 0.0162(6) Uani 1 1 d . . . . .
N2 N 0.4035(3) 0.1587(3) 0.52983(12) 0.0226(6) Uani 1 1 d . . . . .
C12 C 0.7096(4) 0.1612(3) 0.65615(14) 0.0170(7) Uani 1 1 d . . . . .
C9 C 0.6711(4) 0.3240(3) 0.73040(13) 0.0182(7) Uani 1 1 d . . . . .
C7 C 0.2548(4) 0.2311(3) 0.64517(15) 0.0219(7) Uani 1 1 d . . . . .
H7A H 0.198487 0.246764 0.680283 0.033 Uiso 1 1 calc R U . . .
H7B H 0.224316 0.147497 0.628028 0.033 Uiso 1 1 calc R U . . .
H7C H 0.223909 0.296080 0.614066 0.033 Uiso 1 1 calc R U . . .
C17 C 0.1777(4) 0.5484(3) 0.68079(14) 0.0190(7) Uani 1 1 d . . . . .
H17 H 0.087170 0.515959 0.697398 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2509(4) 0.1517(3) 0.49972(14) 0.0218(7) Uani 1 1 d . . . . .
H3 H 0.171491 0.092347 0.508233 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7485(4) 0.4158(3) 0.77836(15) 0.0246(8) Uani 1 1 d . . . . .
H10A H 0.866600 0.404406 0.784511 0.037 Uiso 1 1 calc R U . . .
H10B H 0.707020 0.399952 0.816821 0.037 Uiso 1 1 calc R U . . .
H10C H 0.722012 0.502638 0.764866 0.037 Uiso 1 1 calc R U . . .
C13 C 0.8260(4) 0.0768(3) 0.62918(15) 0.0254(8) Uani 1 1 d . . . . .
H13A H 0.935697 0.088241 0.651527 0.038 Uiso 1 1 calc R U . . .
H13B H 0.825233 0.098954 0.586183 0.038 Uiso 1 1 calc R U . . .
H13C H 0.792805 -0.011617 0.632234 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3918(4) 0.4077(3) 0.73969(14) 0.0204(7) Uani 1 1 d . . . . .
H14A H 0.298902 0.359653 0.751303 0.024 Uiso 1 1 calc R U . . .
H14B H 0.451684 0.446401 0.777061 0.024 Uiso 1 1 calc R U . . .
C16 C 0.3258(4) 0.6583(3) 0.62816(16) 0.0238(7) Uani 1 1 d . . . . .
H16 H 0.358405 0.718064 0.600305 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4258(4) 0.5778(3) 0.66311(16) 0.0250(8) Uani 1 1 d . . . . .
H15 H 0.540136 0.571096 0.664562 0.030 Uiso 1 1 calc R U . . .
C2 C 0.4795(4) 0.2555(5) 0.50570(17) 0.0459(12) Uani 1 1 d . . . . .
H2 H 0.587978 0.283138 0.518084 0.055 Uiso 1 1 calc R U . . .
C1 C 0.3704(4) 0.3055(5) 0.46034(18) 0.0477(13) Uani 1 1 d . . . . .
H1 H 0.389914 0.375018 0.435246 0.057 Uiso 1 1 calc R U . . .
C1A C -0.0053(13) 0.4848(13) 0.5100(6) 0.055(3) Uiso 0.5 1 d D . P A -1
C2A C -0.1159(10) 0.4236(9) 0.5452(4) 0.060(3) Uiso 0.5 1 d D . P A -1
H2A1 H -0.102893 0.460252 0.586301 0.089 Uiso 0.5 1 calc R U P A -1
H2A2 H -0.091919 0.332808 0.548116 0.089 Uiso 0.5 1 calc R U P A -1
H2A3 H -0.227780 0.436211 0.525219 0.089 Uiso 0.5 1 calc R U P A -1
N1A N 0.0681(9) 0.5384(8) 0.4788(3) 0.049(2) Uiso 0.5 1 d D . 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 1.970(3) 3_566 ?
Cu1 N1 1.978(3) . ?
Cu1 Cl1 2.2496(13) . ?
Cu1 Cl2 2.2629(12) . ?
N1 C3 1.325(4) . ?
N1 C1 1.373(5) . ?
N4 C17 1.331(4) . ?
N4 C16 1.373(4) . ?
C5 C6 1.404(4) . ?
C5 C12 1.411(4) . ?
C5 C4 1.511(4) . ?
C4 N2 1.482(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C11 C9 1.381(5) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C8 C6 1.402(4) . ?
C8 C9 1.403(4) . ?
C8 C14 1.510(4) . ?
N3 C17 1.342(4) . ?
N3 C15 1.367(4) . ?
N3 C14 1.473(4) . ?
C6 C7 1.518(4) . ?
N2 C3 1.347(4) . ?
N2 C2 1.354(5) . ?
C12 C13 1.504(4) . ?
C9 C10 1.511(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C17 H17 0.9500 . ?
C3 H3 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C15 1.352(4) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C2 C1 1.358(5) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C1A N1A 1.1385(18) . ?
C1A C2A 1.4455(18) . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
C2A H2A3 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 157.27(11) 3_566 . ?
N4 Cu1 Cl1 93.10(9) 3_566 . ?
N1 Cu1 Cl1 93.00(9) . . ?
N4 Cu1 Cl2 93.34(9) 3_566 . ?
N1 Cu1 Cl2 92.62(9) . . ?
Cl1 Cu1 Cl2 149.00(4) . . ?
C3 N1 C1 106.1(3) . . ?
C3 N1 Cu1 126.7(2) . . ?
C1 N1 Cu1 127.2(2) . . ?
C17 N4 C16 105.9(3) . . ?
C17 N4 Cu1 127.3(2) . 3_566 ?
C16 N4 Cu1 126.8(2) . 3_566 ?
C6 C5 C12 120.1(3) . . ?
C6 C5 C4 120.2(3) . . ?
C12 C5 C4 119.5(3) . . ?
N2 C4 C5 111.2(3) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C9 C11 C12 122.9(3) . . ?
C9 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C6 C8 C9 120.2(3) . . ?
C6 C8 C14 119.6(3) . . ?
C9 C8 C14 120.2(3) . . ?
C17 N3 C15 107.3(3) . . ?
C17 N3 C14 127.9(3) . . ?
C15 N3 C14 124.8(3) . . ?
C8 C6 C5 119.9(3) . . ?
C8 C6 C7 120.1(3) . . ?
C5 C6 C7 120.0(3) . . ?
C3 N2 C2 107.9(3) . . ?
C3 N2 C4 125.8(3) . . ?
C2 N2 C4 126.2(3) . . ?
C11 C12 C5 118.1(3) . . ?
C11 C12 C13 119.2(3) . . ?
C5 C12 C13 122.7(3) . . ?
C11 C9 C8 118.7(3) . . ?
C11 C9 C10 119.0(3) . . ?
C8 C9 C10 122.3(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N4 C17 N3 110.8(3) . . ?
N4 C17 H17 124.6 . . ?
N3 C17 H17 124.6 . . ?
N1 C3 N2 110.3(3) . . ?
N1 C3 H3 124.8 . . ?
N2 C3 H3 124.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C8 110.5(3) . . ?
N3 C14 H14A 109.6 . . ?
C8 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C8 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C15 C16 N4 109.2(3) . . ?
C15 C16 H16 125.4 . . ?
N4 C16 H16 125.4 . . ?
C16 C15 N3 106.9(3) . . ?
C16 C15 H15 126.6 . . ?
N3 C15 H15 126.6 . . ?
N2 C2 C1 106.6(3) . . ?
N2 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C1 N1 109.1(4) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
N1A C1A C2A 172.9(11) . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 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
C6 C5 C4 N2 64.6(4) . . . . ?
C12 C5 C4 N2 -112.3(3) . . . . ?
C9 C8 C6 C5 -1.2(5) . . . . ?
C14 C8 C6 C5 175.5(3) . . . . ?
C9 C8 C6 C7 -179.3(3) . . . . ?
C14 C8 C6 C7 -2.7(4) . . . . ?
C12 C5 C6 C8 3.0(5) . . . . ?
C4 C5 C6 C8 -173.8(3) . . . . ?
C12 C5 C6 C7 -178.8(3) . . . . ?
C4 C5 C6 C7 4.4(5) . . . . ?
C5 C4 N2 C3 -124.6(3) . . . . ?
C5 C4 N2 C2 51.9(5) . . . . ?
C9 C11 C12 C5 -0.9(5) . . . . ?
C9 C11 C12 C13 -179.9(3) . . . . ?
C6 C5 C12 C11 -2.0(5) . . . . ?
C4 C5 C12 C11 174.9(3) . . . . ?
C6 C5 C12 C13 176.9(3) . . . . ?
C4 C5 C12 C13 -6.2(5) . . . . ?
C12 C11 C9 C8 2.8(5) . . . . ?
C12 C11 C9 C10 -176.3(3) . . . . ?
C6 C8 C9 C11 -1.7(5) . . . . ?
C14 C8 C9 C11 -178.3(3) . . . . ?
C6 C8 C9 C10 177.3(3) . . . . ?
C14 C8 C9 C10 0.7(5) . . . . ?
C16 N4 C17 N3 -0.3(4) . . . . ?
Cu1 N4 C17 N3 179.4(2) 3_566 . . . ?
C15 N3 C17 N4 0.6(4) . . . . ?
C14 N3 C17 N4 -179.7(3) . . . . ?
C1 N1 C3 N2 -1.0(4) . . . . ?
Cu1 N1 C3 N2 179.4(2) . . . . ?
C2 N2 C3 N1 1.0(4) . . . . ?
C4 N2 C3 N1 178.0(3) . . . . ?
C17 N3 C14 C8 132.4(3) . . . . ?
C15 N3 C14 C8 -48.0(4) . . . . ?
C6 C8 C14 N3 -71.1(4) . . . . ?
C9 C8 C14 N3 105.6(3) . . . . ?
C17 N4 C16 C15 -0.2(4) . . . . ?
Cu1 N4 C16 C15 -179.9(2) 3_566 . . . ?
N4 C16 C15 N3 0.6(4) . . . . ?
C17 N3 C15 C16 -0.7(4) . . . . ?
C14 N3 C15 C16 179.6(3) . . . . ?
C3 N2 C2 C1 -0.5(5) . . . . ?
C4 N2 C2 C1 -177.5(4) . . . . ?
N2 C2 C1 N1 -0.1(5) . . . . ?
C3 N1 C1 C2 0.6(5) . . . . ?
Cu1 N1 C1 C2 -179.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4B Cl2 0.99 2.81 3.675(4) 146.3 3_556
C3 H3 Cl2 0.95 2.61 3.123(4) 114.3 .
C3 H3 Cl2 0.95 2.62 3.447(4) 146.2 3_556
C14 H14A Cl1 0.99 2.71 3.626(4) 153.4 4_566
C16 H16 Cl2 0.95 2.66 3.149(4) 112.9 3_566
C15 H15 Cl1 0.95 2.76 3.600(4) 148.0 3_666

_refine_diff_density_max         0.798
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.092

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

data_6
_database_code_depnum_ccdc_archive 'CCDC 1569715'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            6
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, C H2 Cl2'
_chemical_formula_sum            'C35 H42 Cl6 Cu2 N8'
_chemical_formula_weight         914.54

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                   8.3498(11)
_cell_length_b                   10.6457(14)
_cell_length_c                   22.378(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.387(2)
_cell_angle_gamma                90
_cell_volume                     1962.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4184
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      27.75

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.530
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8262
_exptl_absorpt_correction_T_max  0.9556
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10291
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         27.751
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4184
_reflns_number_gt                3148
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.9925P] 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         4184
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.02367(4) 0.76309(4) 0.39709(2) 0.01761(13) Uani 1 1 d . . . . .
Cl1 Cl 0.15746(9) 0.79878(9) 0.31843(3) 0.0251(2) Uani 1 1 d . . . . .
Cl2 Cl -0.12056(9) 0.63244(8) 0.44852(4) 0.0253(2) Uani 1 1 d . . . . .
N4 N 0.1733(3) 1.1480(2) 0.64221(11) 0.0174(5) Uani 1 1 d . . . . .
N3 N 0.3340(3) 1.0124(2) 0.69703(11) 0.0186(6) Uani 1 1 d . . . . .
N1 N 0.2256(3) 0.7328(3) 0.45449(11) 0.0206(6) Uani 1 1 d . . . . .
C6 C 0.7067(4) 0.6645(3) 0.65614(13) 0.0178(6) Uani 1 1 d . . . . .
N2 N 0.4009(3) 0.6560(3) 0.52997(11) 0.0204(6) Uani 1 1 d . . . . .
C5 C 0.5383(4) 0.6622(3) 0.63656(13) 0.0169(4) Uani 1 1 d . . . . .
C3 C 0.2478(4) 0.6500(3) 0.49953(13) 0.0199(7) Uani 1 1 d . . . . .
H3 H 0.166770 0.594165 0.509010 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5022(4) 0.8219(3) 0.71117(13) 0.0196(5) Uani 1 1 d . . . . .
C9 C 0.6711(4) 0.8280(3) 0.72925(13) 0.0195(5) Uani 1 1 d . . . . .
C17 C 0.1800(4) 1.0532(3) 0.68115(13) 0.0174(6) Uani 1 1 d . . . . .
H17 H 0.088759 1.018832 0.695799 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4681(4) 0.5799(3) 0.58328(13) 0.0214(7) Uani 1 1 d . . . . .
H4A H 0.554139 0.524182 0.572720 0.026 Uiso 1 1 calc R U . . .
H4B H 0.381256 0.526371 0.594923 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7693(4) 0.7476(3) 0.70223(13) 0.0195(5) Uani 1 1 d . . . . .
H8 H 0.883246 0.749236 0.715690 0.023 Uiso 1 1 calc R U . . .
C14 C 0.3926(4) 0.9096(3) 0.73915(13) 0.0196(5) Uani 1 1 d . . . . .
H14A H 0.298760 0.862047 0.749304 0.023 Uiso 1 1 calc R U . . .
H14B H 0.452963 0.945246 0.777116 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3308(4) 1.1690(3) 0.63382(14) 0.0220(7) Uani 1 1 d . . . . .
H16 H 0.364477 1.232004 0.608490 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4351(4) 0.7391(3) 0.66473(13) 0.0169(4) Uani 1 1 d . . . . .
C10 C 0.7515(4) 0.9202(3) 0.77651(14) 0.0263(8) Uani 1 1 d . . . . .
H10A H 0.869383 0.907744 0.782826 0.039 Uiso 1 1 calc R U . . .
H10B H 0.711202 0.906051 0.814705 0.039 Uiso 1 1 calc R U . . .
H10C H 0.725965 1.006188 0.762544 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2531(4) 0.7345(3) 0.64475(15) 0.0224(7) Uani 1 1 d . . . . .
H13A H 0.198713 0.746021 0.679988 0.034 Uiso 1 1 calc R U . . .
H13B H 0.222645 0.652900 0.626000 0.034 Uiso 1 1 calc R U . . .
H13C H 0.220214 0.801575 0.615319 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8236(4) 0.5805(3) 0.62936(15) 0.0262(7) Uani 1 1 d . . . . .
H7A H 0.819371 0.601008 0.586441 0.039 Uiso 1 1 calc R U . . .
H7B H 0.792841 0.492442 0.633317 0.039 Uiso 1 1 calc R U . . .
H7C H 0.934078 0.593858 0.651037 0.039 Uiso 1 1 calc R U . . .
C1 C 0.3721(4) 0.7940(4) 0.45694(15) 0.0347(9) Uani 1 1 d . . . . .
H1 H 0.393961 0.858750 0.430160 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4302(4) 1.0858(3) 0.66725(14) 0.0237(7) Uani 1 1 d . . . . .
H15 H 0.544535 1.079599 0.669615 0.028 Uiso 1 1 calc R U . . .
C2 C 0.4804(4) 0.7474(4) 0.50359(16) 0.0358(9) Uani 1 1 d . . . . .
H2 H 0.589778 0.773336 0.515513 0.043 Uiso 1 1 calc R U . . .
Cl2A Cl 0.8362(2) 0.92590(18) 0.57823(8) 0.0376(4) Uani 0.5 1 d . . P A -1
Cl1A Cl 1.0220(3) 1.0251(2) 0.48811(10) 0.0481(6) Uani 0.5 1 d . . P A -1
C1A C 0.8376(10) 0.9578(8) 0.5010(3) 0.0377(18) Uani 0.5 1 d . . P A -1
H1A1 H 0.747402 1.015928 0.486018 0.045 Uiso 0.5 1 calc R U P A -1
H1A2 H 0.818806 0.878704 0.477710 0.045 Uiso 0.5 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 1.972(3) . ?
Cu1 N4 1.975(2) 3_576 ?
Cu1 Cl1 2.2655(9) . ?
Cu1 Cl2 2.2719(9) . ?
N4 C17 1.329(4) . ?
N4 C16 1.377(4) . ?
N3 C17 1.349(4) . ?
N3 C15 1.369(4) . ?
N3 C14 1.475(4) . ?
N1 C3 1.329(4) . ?
N1 C1 1.380(4) . ?
C6 C8 1.394(4) . ?
C6 C5 1.404(4) . ?
C6 C7 1.517(4) . ?
N2 C3 1.349(4) . ?
N2 C2 1.365(5) . ?
N2 C4 1.475(4) . ?
C5 C12 1.409(4) . ?
C5 C4 1.518(4) . ?
C3 H3 0.9500 . ?
C11 C9 1.404(4) . ?
C11 C12 1.408(4) . ?
C11 C14 1.513(4) . ?
C9 C8 1.390(5) . ?
C9 C10 1.516(4) . ?
C17 H17 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 H8 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C15 1.352(4) . ?
C16 H16 0.9500 . ?
C12 C13 1.513(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C1 C2 1.358(5) . ?
C1 H1 0.9500 . ?
C15 H15 0.9500 . ?
C2 H2 0.9500 . ?
Cl2A C1A 1.763(7) . ?
Cl1A C1A 1.764(8) . ?
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
N1 Cu1 N4 158.37(11) . 3_576 ?
N1 Cu1 Cl1 93.21(8) . . ?
N4 Cu1 Cl1 93.09(8) 3_576 . ?
N1 Cu1 Cl2 92.14(8) . . ?
N4 Cu1 Cl2 92.70(8) 3_576 . ?
Cl1 Cu1 Cl2 149.95(4) . . ?
C17 N4 C16 105.9(2) . . ?
C17 N4 Cu1 126.8(2) . 3_576 ?
C16 N4 Cu1 127.3(2) . 3_576 ?
C17 N3 C15 107.3(3) . . ?
C17 N3 C14 127.6(3) . . ?
C15 N3 C14 125.1(3) . . ?
C3 N1 C1 105.7(3) . . ?
C3 N1 Cu1 126.9(2) . . ?
C1 N1 Cu1 127.4(2) . . ?
C8 C6 C5 118.5(3) . . ?
C8 C6 C7 118.6(3) . . ?
C5 C6 C7 122.9(3) . . ?
C3 N2 C2 107.7(3) . . ?
C3 N2 C4 125.9(3) . . ?
C2 N2 C4 126.4(3) . . ?
C6 C5 C12 120.3(3) . . ?
C6 C5 C4 119.6(3) . . ?
C12 C5 C4 120.0(3) . . ?
N1 C3 N2 110.8(3) . . ?
N1 C3 H3 124.6 . . ?
N2 C3 H3 124.6 . . ?
C9 C11 C12 120.1(3) . . ?
C9 C11 C14 119.9(3) . . ?
C12 C11 C14 119.8(3) . . ?
C8 C9 C11 118.8(3) . . ?
C8 C9 C10 118.5(3) . . ?
C11 C9 C10 122.7(3) . . ?
N4 C17 N3 110.7(3) . . ?
N4 C17 H17 124.7 . . ?
N3 C17 H17 124.7 . . ?
N2 C4 C5 111.4(3) . . ?
N2 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C9 C8 C6 122.4(3) . . ?
C9 C8 H8 118.8 . . ?
C6 C8 H8 118.8 . . ?
N3 C14 C11 110.7(2) . . ?
N3 C14 H14A 109.5 . . ?
C11 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C15 C16 N4 109.4(3) . . ?
C15 C16 H16 125.3 . . ?
N4 C16 H16 125.3 . . ?
C11 C12 C5 119.7(3) . . ?
C11 C12 C13 119.9(3) . . ?
C5 C12 C13 120.4(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C1 N1 109.4(3) . . ?
C2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?
C16 C15 N3 106.7(3) . . ?
C16 C15 H15 126.7 . . ?
N3 C15 H15 126.7 . . ?
C1 C2 N2 106.5(3) . . ?
C1 C2 H2 126.8 . . ?
N2 C2 H2 126.8 . . ?
Cl2A C1A Cl1A 112.6(4) . . ?
Cl2A C1A H1A1 109.1 . . ?
Cl1A C1A H1A1 109.1 . . ?
Cl2A C1A H1A2 109.1 . . ?
Cl1A C1A H1A2 109.1 . . ?
H1A1 C1A H1A2 107.8 . . ?

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
C8 C6 C5 C12 -2.4(4) . . . . ?
C7 C6 C5 C12 177.6(3) . . . . ?
C8 C6 C5 C4 175.4(3) . . . . ?
C7 C6 C5 C4 -4.7(4) . . . . ?
C1 N1 C3 N2 -0.2(4) . . . . ?
Cu1 N1 C3 N2 -179.3(2) . . . . ?
C2 N2 C3 N1 0.5(4) . . . . ?
C4 N2 C3 N1 178.8(3) . . . . ?
C12 C11 C9 C8 -2.6(4) . . . . ?
C14 C11 C9 C8 -179.1(3) . . . . ?
C12 C11 C9 C10 176.6(3) . . . . ?
C14 C11 C9 C10 0.1(4) . . . . ?
C16 N4 C17 N3 -0.8(3) . . . . ?
Cu1 N4 C17 N3 177.63(19) 3_576 . . . ?
C15 N3 C17 N4 0.7(3) . . . . ?
C14 N3 C17 N4 179.8(3) . . . . ?
C3 N2 C4 C5 -124.1(3) . . . . ?
C2 N2 C4 C5 53.9(4) . . . . ?
C6 C5 C4 N2 -111.1(3) . . . . ?
C12 C5 C4 N2 66.6(4) . . . . ?
C11 C9 C8 C6 2.7(5) . . . . ?
C10 C9 C8 C6 -176.5(3) . . . . ?
C5 C6 C8 C9 -0.2(5) . . . . ?
C7 C6 C8 C9 179.9(3) . . . . ?
C17 N3 C14 C11 131.3(3) . . . . ?
C15 N3 C14 C11 -49.7(4) . . . . ?
C9 C11 C14 N3 103.3(3) . . . . ?
C12 C11 C14 N3 -73.3(4) . . . . ?
C17 N4 C16 C15 0.6(4) . . . . ?
Cu1 N4 C16 C15 -177.8(2) 3_576 . . . ?
C9 C11 C12 C5 0.1(4) . . . . ?
C14 C11 C12 C5 176.6(3) . . . . ?
C9 C11 C12 C13 -179.0(3) . . . . ?
C14 C11 C12 C13 -2.5(4) . . . . ?
C6 C5 C12 C11 2.4(4) . . . . ?
C4 C5 C12 C11 -175.3(3) . . . . ?
C6 C5 C12 C13 -178.5(3) . . . . ?
C4 C5 C12 C13 3.7(4) . . . . ?
C3 N1 C1 C2 -0.2(4) . . . . ?
Cu1 N1 C1 C2 178.9(3) . . . . ?
N4 C16 C15 N3 -0.2(4) . . . . ?
C17 N3 C15 C16 -0.3(4) . . . . ?
C14 N3 C15 C16 -179.4(3) . . . . ?
N1 C1 C2 N2 0.5(5) . . . . ?
C3 N2 C2 C1 -0.6(4) . . . . ?
C4 N2 C2 C1 -178.9(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
C3 H3 Cl2 0.95 2.59 3.107(3) 114.7 .
C3 H3 Cl2 0.95 2.64 3.453(3) 143.3 3_566
C4 H4B Cl2 0.99 2.80 3.656(3) 144.8 3_566
C14 H14A Cl1 0.99 2.70 3.614(3) 153.0 4_576
C16 H16 Cl2 0.95 2.65 3.145(3) 113.2 3_576
C1 H1 Cl2A 0.95 2.98 3.477(5) 114.2 3_676
C15 H15 Cl1 0.95 2.78 3.620(3) 148.1 3_676
C2 H2 Cl2A 0.95 2.81 3.689(4) 154.2 .
C1A H1A2 Cl2 0.99 2.77 3.693(8) 155.6 1_655

_refine_diff_density_max         0.597
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1569709'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            10
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, C5 H4'
_chemical_formula_sum            'C39 H44 Cl4 Cu2 N8'
_chemical_formula_weight         893.72

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'
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                   8.2969(15)
_cell_length_b                   10.771(2)
_cell_length_c                   22.520(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.655(2)
_cell_angle_gamma                90
_cell_volume                     1984.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2529
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      16.44

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.381
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8093
_exptl_absorpt_correction_T_max  0.9217
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11218
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.835
_diffrn_reflns_theta_max         27.795
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4289
_reflns_number_gt                2978
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+4.2754P] 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         4289
_refine_ls_number_parameters     291
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.47527(6) 0.74002(5) 0.10173(2) 0.02982(17) Uani 1 1 d . . . . .
Cl1 Cl 0.62265(14) 0.86846(13) 0.05280(7) 0.0577(4) Uani 1 1 d . . . . .
N1 N 0.2785(11) 0.7539(8) 0.0445(4) 0.0224(16) Uani 0.5 1 d . . P A 1
C1 C 0.1360(9) 0.6821(9) 0.0374(4) 0.0273(18) Uani 0.5 1 d . . P A 1
H1 H 0.118374 0.611955 0.061030 0.033 Uiso 0.5 1 calc R U P A 1
Cl2 Cl 0.34033(13) 0.70348(14) 0.17941(5) 0.0475(4) Uani 1 1 d . . . . .
N2 N 0.1018(12) 0.8301(8) -0.0301(5) 0.0224(16) Uani 0.5 1 d . . P A 1
C2 C 0.0278(10) 0.7285(9) -0.0085(4) 0.029(2) Uani 0.5 1 d . . P A 1
H2 H -0.078552 0.697447 -0.023240 0.035 Uiso 0.5 1 calc R U P A 1
N3 N 0.1710(4) 0.4865(4) -0.19652(17) 0.0344(9) Uani 1 1 d . . . . .
C3 C 0.2510(13) 0.8407(14) 0.0040(5) 0.0224(16) Uani 0.5 1 d . . P A 1
H3 H 0.327149 0.904102 -0.001071 0.027 Uiso 0.5 1 calc R U P A 1
N4 N 0.3307(4) 0.3529(4) -0.14081(17) 0.0347(9) Uani 1 1 d . . . . .
C4 C 0.048(2) 0.9261(17) -0.0924(7) 0.0224(16) Uani 0.5 1 d . . P A 1
H4A H -0.028603 0.992097 -0.084379 0.027 Uiso 0.5 1 calc R U P A 1
H4B H 0.145482 0.964722 -0.104788 0.027 Uiso 0.5 1 calc R U P A 1
C5 C -0.0322(5) 0.8371(4) -0.13857(18) 0.0274(9) Uani 1 1 d . . . . .
C6 C 0.0710(5) 0.7613(4) -0.16597(18) 0.0256(9) Uani 1 1 d . . . . .
C7 C 0.2549(5) 0.7680(5) -0.1469(2) 0.0397(11) Uani 1 1 d . . . . .
H7A H 0.285405 0.851088 -0.131109 0.060 Uiso 1 1 calc R U . . .
H7B H 0.308353 0.751343 -0.181697 0.060 Uiso 1 1 calc R U . . .
H7C H 0.289794 0.706052 -0.115498 0.060 Uiso 1 1 calc R U . . .
C8 C 0.0041(5) 0.6763(4) -0.21126(18) 0.0296(9) Uani 1 1 d . . . . .
C9 C -0.1654(5) 0.6705(4) -0.22976(18) 0.0330(10) Uani 1 1 d . . . . .
C10 C -0.2465(7) 0.5796(5) -0.2762(2) 0.0511(14) Uani 1 1 d . . . . .
H10A H -0.209323 0.594827 -0.314587 0.077 Uiso 1 1 calc R U . . .
H10B H -0.365397 0.589924 -0.281440 0.077 Uiso 1 1 calc R U . . .
H10C H -0.217526 0.494746 -0.262655 0.077 Uiso 1 1 calc R U . . .
C11 C -0.2638(5) 0.7520(4) -0.20368(18) 0.0305(9) Uani 1 1 d . . . . .
H11 H -0.378376 0.750688 -0.217612 0.037 Uiso 1 1 calc R U . . .
C12 C -0.2026(5) 0.8344(4) -0.15855(18) 0.0272(9) Uani 1 1 d . . . . .
C13 C -0.3179(5) 0.9191(4) -0.1325(2) 0.0349(10) Uani 1 1 d . . . . .
H13A H -0.429333 0.907389 -0.154325 0.052 Uiso 1 1 calc R U . . .
H13B H -0.284641 1.005651 -0.136480 0.052 Uiso 1 1 calc R U . . .
H13C H -0.314391 0.899387 -0.089842 0.052 Uiso 1 1 calc R U . . .
C14 C 0.1138(6) 0.5879(4) -0.2385(2) 0.0374(11) Uani 1 1 d . . . . .
H14A H 0.052807 0.552894 -0.276309 0.045 Uiso 1 1 calc R U . . .
H14B H 0.209094 0.633988 -0.248341 0.045 Uiso 1 1 calc R U . . .
C15 C 0.0721(6) 0.4128(6) -0.1687(3) 0.0603(17) Uani 1 1 d . . . . .
H15 H -0.043396 0.418319 -0.172444 0.072 Uiso 1 1 calc R U . . .
C16 C 0.1711(6) 0.3304(6) -0.1349(3) 0.0639(19) Uani 1 1 d . . . . .
H16 H 0.135707 0.266901 -0.110778 0.077 Uiso 1 1 calc R U . . .
C17 C 0.3255(5) 0.4474(4) -0.17861(18) 0.0299(10) Uani 1 1 d . . . . .
H17 H 0.418618 0.483011 -0.191430 0.036 Uiso 1 1 calc R U . . .
N1A N 0.2714(12) 0.7969(8) 0.0449(4) 0.0232(18) Uani 0.5 1 d D . P A 2
C1A C 0.1154(10) 0.7686(9) 0.0513(4) 0.031(2) Uani 0.5 1 d . . P A 2
H1A H 0.084681 0.724498 0.084210 0.037 Uiso 0.5 1 calc R U P A 2
N2A N 0.1009(11) 0.8695(8) -0.0336(5) 0.0232(18) Uani 0.5 1 d D . P A 2
C2A C 0.0098(11) 0.8136(10) 0.0029(4) 0.032(2) Uani 0.5 1 d . . P A 2
H2A H -0.105996 0.806745 -0.003762 0.038 Uiso 0.5 1 calc R U P A 2
C3A C 0.2616(11) 0.8601(14) -0.0081(4) 0.0232(18) Uani 0.5 1 d D . P A 2
H3A H 0.351448 0.892099 -0.024398 0.028 Uiso 0.5 1 calc R U P A 2
C1B C -0.0150(14) 0.4792(9) 0.0288(4) 0.045(3) Uani 0.5 1 d . . P B 3
C2B C 0.1273(14) 0.4451(9) 0.0723(5) 0.048(3) Uani 0.5 1 d . . P B 3
H2B H 0.113795 0.419630 0.111600 0.058 Uiso 0.5 1 calc R U P B 3
C5B C 0.1749(14) 0.5247(10) -0.0412(5) 0.053(3) Uani 0.5 1 d . . P B 3
H5B H 0.192455 0.552290 -0.079676 0.064 Uiso 0.5 1 calc R U P B 3
C3B C 0.2803(15) 0.4490(10) 0.0577(5) 0.053(3) Uani 0.5 1 d . . P B 3
H3B H 0.370260 0.423381 0.086975 0.063 Uiso 0.5 1 calc R U P B 3
C4B C 0.3105(16) 0.4887(11) 0.0019(6) 0.064(3) Uani 0.5 1 d . . P B 3
H4B1 H 0.418407 0.491478 -0.006977 0.077 Uiso 0.5 1 calc R U P B 3
C4A C 0.0271(18) 0.9135(18) -0.0801(6) 0.029(3) Uani 0.5 1 d . . P A 2
H4A1 H 0.096790 0.980909 -0.091674 0.035 Uiso 0.5 1 calc R U P A 2
H4A2 H -0.071326 0.953959 -0.069475 0.035 Uiso 0.5 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.908(9) . ?
Cu1 N4 1.973(4) 3_665 ?
Cu1 N1A 2.037(9) . ?
Cu1 Cl1 2.2529(14) . ?
Cu1 Cl2 2.2639(13) . ?
N1 C3 1.300(11) . ?
N1 C1 1.399(12) . ?
C1 C2 1.346(12) . ?
C1 H1 0.9500 . ?
N2 C3 1.347(10) . ?
N2 C2 1.382(14) . ?
N2 C4 1.74(2) . ?
C2 H2 0.9500 . ?
N3 C17 1.345(5) . ?
N3 C15 1.366(6) . ?
N3 C14 1.470(6) . ?
C3 H3 0.9500 . ?
N4 C17 1.323(6) . ?
N4 C16 1.375(6) . ?
C4 C5 1.486(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.400(6) . ?
C5 C12 1.410(5) . ?
C5 C4A 1.560(17) . ?
C6 C8 1.413(6) . ?
C6 C7 1.516(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.399(6) . ?
C8 C14 1.516(6) . ?
C9 C11 1.393(6) . ?
C9 C10 1.506(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.381(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.510(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.354(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N1A C1A 1.361(13) . ?
N1A C3A 1.364(2) . ?
C1A C2A 1.368(12) . ?
C1A H1A 0.9500 . ?
N2A C4A 1.22(2) . ?
N2A C2A 1.349(15) . ?
N2A C3A 1.364(2) . ?
C2A H2A 0.9500 . ?
C3A H3A 0.9500 . ?
C1B C5B 1.401(15) 3_565 ?
C1B C1B 1.43(2) 3_565 ?
C1B C2B 1.449(15) . ?
C2B C3B 1.365(15) . ?
C2B H2B 0.9500 . ?
C5B C4B 1.411(16) . ?
C5B H5B 0.9500 . ?
C3B C4B 1.390(16) . ?
C3B H3B 0.9500 . ?
C4B H4B1 0.9500 . ?
C4A H4A1 0.9900 . ?
C4A H4A2 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
N1 Cu1 N4 151.9(3) . 3_665 ?
N4 Cu1 N1A 164.2(3) 3_665 . ?
N1 Cu1 Cl1 95.4(3) . . ?
N4 Cu1 Cl1 93.48(11) 3_665 . ?
N1A Cu1 Cl1 88.3(3) . . ?
N1 Cu1 Cl2 93.3(3) . . ?
N4 Cu1 Cl2 92.26(11) 3_665 . ?
N1A Cu1 Cl2 94.1(3) . . ?
Cl1 Cu1 Cl2 149.78(6) . . ?
C3 N1 C1 105.7(8) . . ?
C3 N1 Cu1 124.1(7) . . ?
C1 N1 Cu1 130.2(8) . . ?
C2 C1 N1 109.0(8) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C3 N2 C2 106.7(7) . . ?
C3 N2 C4 119.7(9) . . ?
C2 N2 C4 133.2(10) . . ?
C1 C2 N2 106.6(8) . . ?
C1 C2 H2 126.7 . . ?
N2 C2 H2 126.7 . . ?
C17 N3 C15 107.2(4) . . ?
C17 N3 C14 127.9(4) . . ?
C15 N3 C14 124.9(4) . . ?
N1 C3 N2 112.0(8) . . ?
N1 C3 H3 124.0 . . ?
N2 C3 H3 124.0 . . ?
C17 N4 C16 105.7(4) . . ?
C17 N4 Cu1 127.9(3) . 3_665 ?
C16 N4 Cu1 126.5(3) . 3_665 ?
C5 C4 N2 101.8(11) . . ?
C5 C4 H4A 111.4 . . ?
N2 C4 H4A 111.4 . . ?
C5 C4 H4B 111.4 . . ?
N2 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
C6 C5 C12 120.1(4) . . ?
C6 C5 C4 116.7(7) . . ?
C12 C5 C4 122.9(7) . . ?
C6 C5 C4A 123.4(6) . . ?
C12 C5 C4A 115.9(6) . . ?
C5 C6 C8 120.1(4) . . ?
C5 C6 C7 120.5(4) . . ?
C8 C6 C7 119.4(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C6 119.8(4) . . ?
C9 C8 C14 119.6(4) . . ?
C6 C8 C14 120.6(4) . . ?
C11 C9 C8 118.5(4) . . ?
C11 C9 C10 118.5(4) . . ?
C8 C9 C10 123.0(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 123.1(4) . . ?
C12 C11 H11 118.4 . . ?
C9 C11 H11 118.4 . . ?
C11 C12 C5 118.2(4) . . ?
C11 C12 C13 119.7(4) . . ?
C5 C12 C13 122.0(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C8 111.0(3) . . ?
N3 C14 H14A 109.4 . . ?
C8 C14 H14A 109.4 . . ?
N3 C14 H14B 109.4 . . ?
C8 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 N3 106.5(4) . . ?
C16 C15 H15 126.7 . . ?
N3 C15 H15 126.7 . . ?
C15 C16 N4 109.4(4) . . ?
C15 C16 H16 125.3 . . ?
N4 C16 H16 125.3 . . ?
N4 C17 N3 111.1(4) . . ?
N4 C17 H17 124.4 . . ?
N3 C17 H17 124.4 . . ?
C1A N1A C3A 106.6(7) . . ?
C1A N1A Cu1 124.8(7) . . ?
C3A N1A Cu1 128.4(6) . . ?
N1A C1A C2A 109.2(8) . . ?
N1A C1A H1A 125.4 . . ?
C2A C1A H1A 125.4 . . ?
C4A N2A C2A 116.5(11) . . ?
C4A N2A C3A 135.0(10) . . ?
C2A N2A C3A 108.5(7) . . ?
N2A C2A C1A 107.2(8) . . ?
N2A C2A H2A 126.4 . . ?
C1A C2A H2A 126.4 . . ?
N1A C3A N2A 108.5(6) . . ?
N1A C3A H3A 125.8 . . ?
N2A C3A H3A 125.8 . . ?
C5B C1B C2B 123.3(10) 3_565 . ?
C1B C1B C2B 116.5(13) 3_565 . ?
C3B C2B C1B 120.9(10) . . ?
C3B C2B H2B 119.5 . . ?
C1B C2B H2B 119.5 . . ?
C1B C5B C4B 121.8(11) 3_565 . ?
C1B C5B H5B 119.1 3_565 . ?
C4B C5B H5B 119.1 . . ?
C2B C3B C4B 122.9(11) . . ?
C2B C3B H3B 118.5 . . ?
C4B C3B H3B 118.5 . . ?
C3B C4B C5B 117.6(12) . . ?
C3B C4B H4B1 121.2 . . ?
C5B C4B H4B1 121.2 . . ?
N2A C4A C5 124.2(15) . . ?
N2A C4A H4A1 106.3 . . ?
C5 C4A H4A1 106.3 . . ?
N2A C4A H4A2 106.3 . . ?
C5 C4A H4A2 106.3 . . ?
H4A1 C4A H4A2 106.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 0.8(12) . . . . ?
Cu1 N1 C1 C2 178.8(7) . . . . ?
N1 C1 C2 N2 -0.3(11) . . . . ?
C3 N2 C2 C1 -0.3(13) . . . . ?
C4 N2 C2 C1 172.4(11) . . . . ?
C1 N1 C3 N2 -1.0(15) . . . . ?
Cu1 N1 C3 N2 -179.2(6) . . . . ?
C2 N2 C3 N1 0.9(15) . . . . ?
C4 N2 C3 N1 -173.0(10) . . . . ?
C3 N2 C4 C5 136.1(11) . . . . ?
C2 N2 C4 C5 -35.9(16) . . . . ?
N2 C4 C5 C6 -78.3(9) . . . . ?
N2 C4 C5 C12 107.1(9) . . . . ?
C12 C5 C6 C8 -3.8(6) . . . . ?
C4 C5 C6 C8 -178.5(8) . . . . ?
C4A C5 C6 C8 167.3(7) . . . . ?
C12 C5 C6 C7 177.0(4) . . . . ?
C4 C5 C6 C7 2.3(9) . . . . ?
C4A C5 C6 C7 -11.9(9) . . . . ?
C5 C6 C8 C9 1.7(6) . . . . ?
C7 C6 C8 C9 -179.1(4) . . . . ?
C5 C6 C8 C14 -176.1(4) . . . . ?
C7 C6 C8 C14 3.1(6) . . . . ?
C6 C8 C9 C11 1.6(6) . . . . ?
C14 C8 C9 C11 179.4(4) . . . . ?
C6 C8 C9 C10 -177.8(4) . . . . ?
C14 C8 C9 C10 0.0(7) . . . . ?
C8 C9 C11 C12 -2.9(7) . . . . ?
C10 C9 C11 C12 176.5(4) . . . . ?
C9 C11 C12 C5 0.8(7) . . . . ?
C9 C11 C12 C13 -179.7(4) . . . . ?
C6 C5 C12 C11 2.6(6) . . . . ?
C4 C5 C12 C11 177.0(8) . . . . ?
C4A C5 C12 C11 -169.2(7) . . . . ?
C6 C5 C12 C13 -176.9(4) . . . . ?
C4 C5 C12 C13 -2.5(9) . . . . ?
C4A C5 C12 C13 11.4(9) . . . . ?
C17 N3 C14 C8 -128.8(5) . . . . ?
C15 N3 C14 C8 51.9(7) . . . . ?
C9 C8 C14 N3 -102.9(5) . . . . ?
C6 C8 C14 N3 74.9(5) . . . . ?
C17 N3 C15 C16 -0.3(7) . . . . ?
C14 N3 C15 C16 179.1(5) . . . . ?
N3 C15 C16 N4 0.7(8) . . . . ?
C17 N4 C16 C15 -0.7(7) . . . . ?
Cu1 N4 C16 C15 -179.6(4) 3_665 . . . ?
C16 N4 C17 N3 0.5(6) . . . . ?
Cu1 N4 C17 N3 179.4(3) 3_665 . . . ?
C15 N3 C17 N4 -0.1(6) . . . . ?
C14 N3 C17 N4 -179.5(4) . . . . ?
C3A N1A C1A C2A 0.0(13) . . . . ?
Cu1 N1A C1A C2A -175.3(7) . . . . ?
C4A N2A C2A C1A 178.6(12) . . . . ?
C3A N2A C2A C1A -0.3(13) . . . . ?
N1A C1A C2A N2A 0.2(12) . . . . ?
C1A N1A C3A N2A -0.2(14) . . . . ?
Cu1 N1A C3A N2A 174.9(6) . . . . ?
C4A N2A C3A N1A -178.4(16) . . . . ?
C2A N2A C3A N1A 0.3(14) . . . . ?
C5B C1B C2B C3B 179.2(10) 3_565 . . . ?
C1B C1B C2B C3B -2.2(17) 3_565 . . . ?
C1B C2B C3B C4B 2.0(17) . . . . ?
C2B C3B C4B C5B -0.8(17) . . . . ?
C1B C5B C4B C3B -0.1(16) 3_565 . . . ?
C2A N2A C4A C5 -82.1(13) . . . . ?
C3A N2A C4A C5 96.5(17) . . . . ?
C6 C5 C4A N2A -53.1(15) . . . . ?
C12 C5 C4A N2A 118.4(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 Cl1 0.95 2.58 3.110(11) 115.9 .
C3 H3 Cl1 0.95 2.77 3.605(14) 146.6 3_675
C4 H4B Cl1 0.99 2.75 3.513(17) 134.6 3_675
C14 H14B Cl2 0.99 2.74 3.629(5) 150.1 4_575
C15 H15 Cl2 0.95 2.77 3.614(5) 148.2 3_565
C16 H16 Cl1 0.95 2.64 3.142(5) 113.5 3_665
C1A H1A Cl2 0.95 2.76 3.239(8) 112.0 .
C2A H2A Cl1 0.95 2.85 3.625(10) 140.0 1_455
C3A H3A Cl1 0.95 2.61 3.080(9) 110.6 .
C3A H3A Cl1 0.95 2.67 3.288(14) 122.8 3_675
C4A H4A1 Cl1 0.99 2.85 3.707(17) 145.0 3_675

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1569718'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        9
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, C H Cl3'
_chemical_formula_sum            'C35 H41 Cl7 Cu2 N8'
_chemical_formula_weight         948.99

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                   16.671(2)
_cell_length_b                   10.7795(15)
_cell_length_c                   22.437(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.497(2)
_cell_angle_gamma                90
_cell_volume                     3976.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8607
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      27.79

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.578
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8841
_exptl_absorpt_correction_T_max  0.9396
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22696
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.841
_diffrn_reflns_theta_max         27.786
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8617
_reflns_number_gt                5798
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+4.1648P] 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         8617
_refine_ls_number_parameters     475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.76287(3) 0.26059(4) 0.39309(2) 0.01435(12) Uani 1 1 d . . . . .
Cu2 Cu 0.74031(3) 0.74841(4) 0.60051(2) 0.01375(12) Uani 1 1 d . . . . .
Cl3 Cl 0.67637(5) 0.72855(9) 0.68235(4) 0.0172(2) Uani 1 1 d . . . . .
Cl1 Cl 0.83051(6) 0.31053(10) 0.31740(4) 0.0215(2) Uani 1 1 d . . . . .
Cl2 Cl 0.69261(6) 0.13176(9) 0.44617(4) 0.0209(2) Uani 1 1 d . . . . .
Cl4 Cl 0.81623(6) 0.86821(9) 0.54770(5) 0.0241(2) Uani 1 1 d . . . . .
N4 N 0.83473(19) 0.6510(3) 0.63866(14) 0.0163(7) Uani 1 1 d . . . . .
N8 N 0.66086(19) 0.3390(3) 0.35186(14) 0.0157(7) Uani 1 1 d . . . . .
C33 C 0.5819(2) 0.3019(4) 0.35315(17) 0.0184(8) Uani 1 1 d . . . . .
H33 H 0.566513 0.231014 0.373730 0.022 Uiso 1 1 calc R U . . .
C10 C 1.1143(3) 0.4211(4) 0.77979(18) 0.0243(10) Uani 1 1 d . . . . .
H10A H 1.102323 0.506274 0.765748 0.036 Uiso 1 1 calc R U . . .
H10B H 1.173303 0.409115 0.788689 0.036 Uiso 1 1 calc R U . . .
H10C H 1.090850 0.406436 0.816457 0.036 Uiso 1 1 calc R U . . .
N6 N 0.55369(18) 0.8582(3) 0.46740(13) 0.0151(7) Uani 1 1 d . . . . .
C32 C 0.5299(2) 0.3822(3) 0.32060(17) 0.0180(8) Uani 1 1 d . . . . .
H32 H 0.472185 0.378557 0.314342 0.022 Uiso 1 1 calc R U . . .
N7 N 0.57657(18) 0.4700(3) 0.29834(14) 0.0157(7) Uani 1 1 d . . . . .
C20 C 0.5606(2) 0.7584(4) 0.55239(18) 0.0204(9) Uani 1 1 d . . . . .
H20 H 0.545959 0.714333 0.585654 0.025 Uiso 1 1 calc R U . . .
C28 C 0.4940(2) 0.6622(3) 0.29062(16) 0.0152(8) Uani 1 1 d . . . . .
C18 C 0.6319(2) 0.8495(3) 0.49367(16) 0.0152(8) Uani 1 1 d . . . . .
H18 H 0.676421 0.882886 0.477370 0.018 Uiso 1 1 calc R U . . .
N1 N 0.86390(19) 0.2367(3) 0.45204(14) 0.0186(7) Uani 1 1 d . . . . .
C4 C 0.9857(2) 0.0891(4) 0.58121(17) 0.0191(9) Uani 1 1 d . . . . .
H4A H 1.030722 0.037938 0.570784 0.023 Uiso 1 1 calc R U . . .
H4B H 0.943241 0.032398 0.591349 0.023 Uiso 1 1 calc R U . . .
N3 N 0.90992(19) 0.5114(3) 0.69335(14) 0.0170(7) Uani 1 1 d . . . . .
C11 C 0.9939(2) 0.3232(3) 0.71025(17) 0.0174(8) Uani 1 1 d . . . . .
N2 N 0.95140(19) 0.1656(3) 0.52861(14) 0.0181(7) Uani 1 1 d . . . . .
N5 N 0.63861(19) 0.7881(3) 0.54540(14) 0.0150(7) Uani 1 1 d . . . . .
C17 C 0.8348(2) 0.5583(3) 0.67769(16) 0.0157(8) Uani 1 1 d . . . . .
H17 H 0.788089 0.529100 0.692514 0.019 Uiso 1 1 calc R U . . .
C21 C 0.5230(2) 0.9207(3) 0.40942(17) 0.0173(8) Uani 1 1 d . . . . .
H21A H 0.568780 0.963357 0.394918 0.021 Uiso 1 1 calc R U . . .
H21B H 0.482737 0.984525 0.416121 0.021 Uiso 1 1 calc R U . . .
C9 C 1.0775(2) 0.3305(3) 0.73087(17) 0.0176(8) Uani 1 1 d . . . . .
C5 C 1.0172(2) 0.1689(3) 0.63560(16) 0.0146(8) Uani 1 1 d . . . . .
C8 C 1.1290(2) 0.2527(3) 0.70520(17) 0.0186(8) Uani 1 1 d . . . . .
H8 H 1.185608 0.254855 0.720583 0.022 Uiso 1 1 calc R U . . .
C34 C 0.6550(2) 0.4391(3) 0.31728(16) 0.0145(8) Uani 1 1 d . . . . .
H34 H 0.700086 0.483398 0.307135 0.017 Uiso 1 1 calc R U . . .
C23 C 0.3988(2) 0.8294(3) 0.34574(16) 0.0146(8) Uani 1 1 d . . . . .
C22 C 0.4838(2) 0.8309(3) 0.36128(16) 0.0131(8) Uani 1 1 d . . . . .
C19 C 0.5077(2) 0.8018(4) 0.50447(18) 0.0210(9) Uani 1 1 d . . . . .
H19 H 0.450130 0.794366 0.498022 0.025 Uiso 1 1 calc R U . . .
C6 C 1.1013(2) 0.1722(3) 0.65812(17) 0.0163(8) Uani 1 1 d . . . . .
C31 C 0.5450(2) 0.5746(3) 0.25946(17) 0.0173(8) Uani 1 1 d . . . . .
H31A H 0.511540 0.542191 0.222139 0.021 Uiso 1 1 calc R U . . .
H31B H 0.591185 0.621016 0.247677 0.021 Uiso 1 1 calc R U . . .
C1 C 0.9330(2) 0.3100(5) 0.45878(19) 0.0294(11) Uani 1 1 d . . . . .
H1 H 0.940900 0.379325 0.434251 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8769(2) 0.1520(4) 0.49528(17) 0.0180(8) Uani 1 1 d . . . . .
H3 H 0.838814 0.090073 0.501932 0.022 Uiso 1 1 calc R U . . .
C24 C 0.3439(2) 0.9180(4) 0.37276(19) 0.0215(9) Uani 1 1 d . . . . .
H24A H 0.287153 0.902641 0.354706 0.032 Uiso 1 1 calc R U . . .
H24B H 0.358454 1.003671 0.364494 0.032 Uiso 1 1 calc R U . . .
H24C H 0.350658 0.905016 0.416531 0.032 Uiso 1 1 calc R U . . .
C26 C 0.4088(2) 0.6580(3) 0.27606(16) 0.0151(8) Uani 1 1 d . . . . .
C7 C 1.1619(2) 0.0917(4) 0.63232(19) 0.0243(9) Uani 1 1 d . . . . .
H7A H 1.216692 0.107004 0.654530 0.036 Uiso 1 1 calc R U . . .
H7B H 1.160242 0.111918 0.589553 0.036 Uiso 1 1 calc R U . . .
H7C H 1.147852 0.004088 0.636213 0.036 Uiso 1 1 calc R U . . .
C13 C 0.8723(2) 0.2350(4) 0.64033(19) 0.0211(9) Uani 1 1 d . . . . .
H13A H 0.842994 0.242066 0.674616 0.032 Uiso 1 1 calc R U . . .
H13B H 0.859000 0.155556 0.619812 0.032 Uiso 1 1 calc R U . . .
H13C H 0.856223 0.303129 0.611951 0.032 Uiso 1 1 calc R U . . .
C16 C 0.9140(2) 0.6634(4) 0.62916(19) 0.0236(9) Uani 1 1 d . . . . .
H16 H 0.932748 0.722199 0.603036 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9363(2) 0.4093(4) 0.73629(17) 0.0198(9) Uani 1 1 d . . . . .
H14A H 0.888201 0.362085 0.744178 0.024 Uiso 1 1 calc R U . . .
H14B H 0.964008 0.444110 0.775114 0.024 Uiso 1 1 calc R U . . .
C29 C 0.5317(2) 0.7489(3) 0.33303(16) 0.0142(8) Uani 1 1 d . . . . .
C15 C 0.9612(3) 0.5778(4) 0.66329(19) 0.0249(10) Uani 1 1 d . . . . .
H15 H 1.018169 0.566271 0.665789 0.030 Uiso 1 1 calc R U . . .
C25 C 0.3634(2) 0.7428(3) 0.30342(17) 0.0161(8) Uani 1 1 d . . . . .
H25 H 0.305835 0.741570 0.292731 0.019 Uiso 1 1 calc R U . . .
C12 C 0.9631(2) 0.2415(3) 0.66292(17) 0.0154(8) Uani 1 1 d . . . . .
C27 C 0.3624(2) 0.5665(4) 0.23193(18) 0.0203(9) Uani 1 1 d . . . . .
H27A H 0.381334 0.572849 0.192930 0.031 Uiso 1 1 calc R U . . .
H27B H 0.304192 0.585323 0.226549 0.031 Uiso 1 1 calc R U . . .
H27C H 0.371857 0.482061 0.247775 0.031 Uiso 1 1 calc R U . . .
C30 C 0.6235(2) 0.7555(4) 0.34638(18) 0.0190(8) Uani 1 1 d . . . . .
H30A H 0.644271 0.690281 0.375284 0.029 Uiso 1 1 calc R U . . .
H30B H 0.640214 0.836785 0.363636 0.029 Uiso 1 1 calc R U . . .
H30C H 0.645453 0.743632 0.308873 0.029 Uiso 1 1 calc R U . . .
C2 C 0.9876(3) 0.2675(5) 0.5057(2) 0.0311(11) Uani 1 1 d . . . . .
H2 H 1.040016 0.300588 0.520142 0.037 Uiso 1 1 calc R U . . .
Cl3A Cl 0.41839(7) 0.47106(10) 0.54382(5) 0.0304(3) Uani 1 1 d . . . . .
Cl2A Cl 0.24325(7) 0.48252(12) 0.50968(6) 0.0429(3) Uani 1 1 d . . . . .
Cl1A Cl 0.34686(8) 0.56720(12) 0.42631(5) 0.0399(3) Uani 1 1 d . . . . .
C1A C 0.3359(3) 0.5544(4) 0.5034(2) 0.0301(10) Uani 1 1 d . . . . .
H1A H 0.335860 0.639721 0.520925 0.036 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 N1 1.979(3) . ?
Cu1 N8 1.986(3) . ?
Cu1 Cl1 2.2533(11) . ?
Cu1 Cl2 2.2758(11) . ?
Cu2 N4 1.967(3) . ?
Cu2 N5 1.974(3) . ?
Cu2 Cl4 2.2734(11) . ?
Cu2 Cl3 2.2803(11) . ?
N4 C17 1.329(5) . ?
N4 C16 1.380(5) . ?
N8 C34 1.323(5) . ?
N8 C33 1.381(5) . ?
C33 C32 1.351(5) . ?
C33 H33 0.9500 . ?
C10 C9 1.521(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N6 C18 1.343(5) . ?
N6 C19 1.364(5) . ?
N6 C21 1.479(4) . ?
C32 N7 1.371(5) . ?
C32 H32 0.9500 . ?
N7 C34 1.348(5) . ?
N7 C31 1.468(4) . ?
C20 C19 1.356(5) . ?
C20 N5 1.373(5) . ?
C20 H20 0.9500 . ?
C28 C26 1.404(5) . ?
C28 C29 1.407(5) . ?
C28 C31 1.517(5) . ?
C18 N5 1.325(5) . ?
C18 H18 0.9500 . ?
N1 C3 1.323(5) . ?
N1 C1 1.385(5) . ?
C4 N2 1.475(5) . ?
C4 C5 1.514(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N3 C17 1.342(5) . ?
N3 C15 1.374(5) . ?
N3 C14 1.481(5) . ?
C11 C9 1.397(5) . ?
C11 C12 1.410(5) . ?
C11 C14 1.520(5) . ?
N2 C3 1.348(5) . ?
N2 C2 1.392(5) . ?
C17 H17 0.9500 . ?
C21 C22 1.516(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C9 C8 1.391(6) . ?
C5 C12 1.409(5) . ?
C5 C6 1.410(5) . ?
C8 C6 1.386(5) . ?
C8 H8 0.9500 . ?
C34 H34 0.9500 . ?
C23 C25 1.391(5) . ?
C23 C22 1.402(5) . ?
C23 C24 1.517(5) . ?
C22 C29 1.411(5) . ?
C19 H19 0.9500 . ?
C6 C7 1.518(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C1 C2 1.353(6) . ?
C1 H1 0.9500 . ?
C3 H3 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 C25 1.393(5) . ?
C26 C27 1.516(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C13 C12 1.517(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 C15 1.363(5) . ?
C16 H16 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C29 C30 1.511(5) . ?
C15 H15 0.9500 . ?
C25 H25 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C2 H2 0.9500 . ?
Cl3A C1A 1.763(5) . ?
Cl2A C1A 1.754(5) . ?
Cl1A C1A 1.775(5) . ?
C1A H1A 1.0000 . ?

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 N8 159.33(13) . . ?
N1 Cu1 Cl1 93.34(10) . . ?
N8 Cu1 Cl1 92.51(10) . . ?
N1 Cu1 Cl2 91.46(10) . . ?
N8 Cu1 Cl2 91.63(10) . . ?
Cl1 Cu1 Cl2 154.82(4) . . ?
N4 Cu2 N5 158.68(13) . . ?
N4 Cu2 Cl4 93.20(10) . . ?
N5 Cu2 Cl4 92.57(10) . . ?
N4 Cu2 Cl3 92.66(10) . . ?
N5 Cu2 Cl3 93.29(10) . . ?
Cl4 Cu2 Cl3 147.94(4) . . ?
C17 N4 C16 106.1(3) . . ?
C17 N4 Cu2 127.0(3) . . ?
C16 N4 Cu2 126.8(3) . . ?
C34 N8 C33 105.6(3) . . ?
C34 N8 Cu1 126.5(3) . . ?
C33 N8 Cu1 127.8(3) . . ?
C32 C33 N8 109.4(4) . . ?
C32 C33 H33 125.3 . . ?
N8 C33 H33 125.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C18 N6 C19 107.7(3) . . ?
C18 N6 C21 125.9(3) . . ?
C19 N6 C21 126.3(3) . . ?
C33 C32 N7 106.7(3) . . ?
C33 C32 H32 126.7 . . ?
N7 C32 H32 126.7 . . ?
C34 N7 C32 107.1(3) . . ?
C34 N7 C31 127.7(3) . . ?
C32 N7 C31 125.2(3) . . ?
C19 C20 N5 109.5(4) . . ?
C19 C20 H20 125.3 . . ?
N5 C20 H20 125.3 . . ?
C26 C28 C29 120.1(3) . . ?
C26 C28 C31 119.7(3) . . ?
C29 C28 C31 120.2(3) . . ?
N5 C18 N6 110.8(3) . . ?
N5 C18 H18 124.6 . . ?
N6 C18 H18 124.6 . . ?
C3 N1 C1 106.3(3) . . ?
C3 N1 Cu1 126.7(3) . . ?
C1 N1 Cu1 126.9(3) . . ?
N2 C4 C5 111.4(3) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C17 N3 C15 107.7(3) . . ?
C17 N3 C14 127.9(3) . . ?
C15 N3 C14 124.4(3) . . ?
C9 C11 C12 120.3(4) . . ?
C9 C11 C14 119.9(4) . . ?
C12 C11 C14 119.7(3) . . ?
C3 N2 C2 107.3(3) . . ?
C3 N2 C4 125.7(3) . . ?
C2 N2 C4 127.0(3) . . ?
C18 N5 C20 105.8(3) . . ?
C18 N5 Cu2 126.6(3) . . ?
C20 N5 Cu2 127.6(3) . . ?
N4 C17 N3 110.8(3) . . ?
N4 C17 H17 124.6 . . ?
N3 C17 H17 124.6 . . ?
N6 C21 C22 112.4(3) . . ?
N6 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
N6 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C8 C9 C11 118.6(4) . . ?
C8 C9 C10 118.9(3) . . ?
C11 C9 C10 122.4(4) . . ?
C12 C5 C6 120.0(3) . . ?
C12 C5 C4 120.3(3) . . ?
C6 C5 C4 119.7(3) . . ?
C6 C8 C9 122.8(4) . . ?
C6 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
N8 C34 N7 111.2(3) . . ?
N8 C34 H34 124.4 . . ?
N7 C34 H34 124.4 . . ?
C25 C23 C22 118.4(3) . . ?
C25 C23 C24 118.6(3) . . ?
C22 C23 C24 123.0(3) . . ?
C23 C22 C29 120.3(3) . . ?
C23 C22 C21 119.0(3) . . ?
C29 C22 C21 120.7(3) . . ?
C20 C19 N6 106.2(4) . . ?
C20 C19 H19 126.9 . . ?
N6 C19 H19 126.9 . . ?
C8 C6 C5 118.4(4) . . ?
C8 C6 C7 119.3(3) . . ?
C5 C6 C7 122.3(3) . . ?
N7 C31 C28 112.2(3) . . ?
N7 C31 H31A 109.2 . . ?
C28 C31 H31A 109.2 . . ?
N7 C31 H31B 109.2 . . ?
C28 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C2 C1 N1 109.4(4) . . ?
C2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?
N1 C3 N2 110.9(3) . . ?
N1 C3 H3 124.6 . . ?
N2 C3 H3 124.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 C26 C28 118.6(3) . . ?
C25 C26 C27 117.4(3) . . ?
C28 C26 C27 124.0(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C16 N4 109.0(4) . . ?
C15 C16 H16 125.5 . . ?
N4 C16 H16 125.5 . . ?
N3 C14 C11 110.0(3) . . ?
N3 C14 H14A 109.7 . . ?
C11 C14 H14A 109.7 . . ?
N3 C14 H14B 109.7 . . ?
C11 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C28 C29 C22 119.8(3) . . ?
C28 C29 C30 119.4(3) . . ?
C22 C29 C30 120.8(3) . . ?
C16 C15 N3 106.3(4) . . ?
C16 C15 H15 126.9 . . ?
N3 C15 H15 126.9 . . ?
C23 C25 C26 122.7(3) . . ?
C23 C25 H25 118.6 . . ?
C26 C25 H25 118.6 . . ?
C5 C12 C11 119.7(3) . . ?
C5 C12 C13 120.3(3) . . ?
C11 C12 C13 120.0(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C1 C2 N2 106.1(4) . . ?
C1 C2 H2 126.9 . . ?
N2 C2 H2 126.9 . . ?
Cl2A C1A Cl3A 110.9(2) . . ?
Cl2A C1A Cl1A 110.2(2) . . ?
Cl3A C1A Cl1A 110.1(3) . . ?
Cl2A C1A H1A 108.5 . . ?
Cl3A C1A H1A 108.5 . . ?
Cl1A C1A H1A 108.5 . . ?

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
C34 N8 C33 C32 -1.6(4) . . . . ?
Cu1 N8 C33 C32 178.2(3) . . . . ?
N8 C33 C32 N7 0.4(4) . . . . ?
C33 C32 N7 C34 0.9(4) . . . . ?
C33 C32 N7 C31 179.0(3) . . . . ?
C19 N6 C18 N5 1.2(4) . . . . ?
C21 N6 C18 N5 179.7(3) . . . . ?
C5 C4 N2 C3 -127.6(4) . . . . ?
C5 C4 N2 C2 49.4(5) . . . . ?
N6 C18 N5 C20 -0.9(4) . . . . ?
N6 C18 N5 Cu2 179.1(2) . . . . ?
C19 C20 N5 C18 0.4(4) . . . . ?
C19 C20 N5 Cu2 -179.7(3) . . . . ?
C16 N4 C17 N3 0.0(4) . . . . ?
Cu2 N4 C17 N3 178.6(2) . . . . ?
C15 N3 C17 N4 0.5(4) . . . . ?
C14 N3 C17 N4 178.9(3) . . . . ?
C18 N6 C21 C22 115.2(4) . . . . ?
C19 N6 C21 C22 -66.6(5) . . . . ?
C12 C11 C9 C8 -2.2(6) . . . . ?
C14 C11 C9 C8 -178.4(3) . . . . ?
C12 C11 C9 C10 177.2(4) . . . . ?
C14 C11 C9 C10 0.9(6) . . . . ?
N2 C4 C5 C12 65.1(5) . . . . ?
N2 C4 C5 C6 -113.5(4) . . . . ?
C11 C9 C8 C6 3.0(6) . . . . ?
C10 C9 C8 C6 -176.4(4) . . . . ?
C33 N8 C34 N7 2.2(4) . . . . ?
Cu1 N8 C34 N7 -177.6(2) . . . . ?
C32 N7 C34 N8 -2.0(4) . . . . ?
C31 N7 C34 N8 -180.0(3) . . . . ?
C25 C23 C22 C29 1.9(5) . . . . ?
C24 C23 C22 C29 -177.8(3) . . . . ?
C25 C23 C22 C21 -177.2(3) . . . . ?
C24 C23 C22 C21 3.0(5) . . . . ?
N6 C21 C22 C23 105.6(4) . . . . ?
N6 C21 C22 C29 -73.6(4) . . . . ?
N5 C20 C19 N6 0.3(5) . . . . ?
C18 N6 C19 C20 -0.9(4) . . . . ?
C21 N6 C19 C20 -179.4(3) . . . . ?
C9 C8 C6 C5 -0.3(6) . . . . ?
C9 C8 C6 C7 179.3(4) . . . . ?
C12 C5 C6 C8 -3.3(5) . . . . ?
C4 C5 C6 C8 175.4(3) . . . . ?
C12 C5 C6 C7 177.2(4) . . . . ?
C4 C5 C6 C7 -4.1(6) . . . . ?
C34 N7 C31 C28 -120.0(4) . . . . ?
C32 N7 C31 C28 62.3(5) . . . . ?
C26 C28 C31 N7 -102.6(4) . . . . ?
C29 C28 C31 N7 78.6(4) . . . . ?
C3 N1 C1 C2 0.8(5) . . . . ?
Cu1 N1 C1 C2 177.0(3) . . . . ?
C1 N1 C3 N2 -1.3(5) . . . . ?
Cu1 N1 C3 N2 -177.5(3) . . . . ?
C2 N2 C3 N1 1.3(5) . . . . ?
C4 N2 C3 N1 178.8(3) . . . . ?
C29 C28 C26 C25 1.4(5) . . . . ?
C31 C28 C26 C25 -177.3(3) . . . . ?
C29 C28 C26 C27 -178.8(3) . . . . ?
C31 C28 C26 C27 2.5(5) . . . . ?
C17 N4 C16 C15 -0.4(5) . . . . ?
Cu2 N4 C16 C15 -179.1(3) . . . . ?
C17 N3 C14 C11 136.8(4) . . . . ?
C15 N3 C14 C11 -45.1(5) . . . . ?
C9 C11 C14 N3 102.5(4) . . . . ?
C12 C11 C14 N3 -73.8(4) . . . . ?
C26 C28 C29 C22 0.5(5) . . . . ?
C31 C28 C29 C22 179.3(3) . . . . ?
C26 C28 C29 C30 -177.6(3) . . . . ?
C31 C28 C29 C30 1.1(5) . . . . ?
C23 C22 C29 C28 -2.2(5) . . . . ?
C21 C22 C29 C28 176.9(3) . . . . ?
C23 C22 C29 C30 175.9(3) . . . . ?
C21 C22 C29 C30 -4.9(5) . . . . ?
N4 C16 C15 N3 0.7(5) . . . . ?
C17 N3 C15 C16 -0.7(5) . . . . ?
C14 N3 C15 C16 -179.2(4) . . . . ?
C22 C23 C25 C26 0.1(6) . . . . ?
C24 C23 C25 C26 179.8(4) . . . . ?
C28 C26 C25 C23 -1.7(6) . . . . ?
C27 C26 C25 C23 178.4(3) . . . . ?
C6 C5 C12 C11 4.0(5) . . . . ?
C4 C5 C12 C11 -174.6(3) . . . . ?
C6 C5 C12 C13 -177.9(3) . . . . ?
C4 C5 C12 C13 3.4(5) . . . . ?
C9 C11 C12 C5 -1.3(6) . . . . ?
C14 C11 C12 C5 175.0(3) . . . . ?
C9 C11 C12 C13 -179.4(3) . . . . ?
C14 C11 C12 C13 -3.1(5) . . . . ?
N1 C1 C2 N2 0.0(5) . . . . ?
C3 N2 C2 C1 -0.7(5) . . . . ?
C4 N2 C2 C1 -178.2(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
C33 H33 Cl2 0.95 2.66 3.140(4) 111.8 .
C32 H32 Cl3 0.95 2.74 3.630(4) 155.5 3_666
C18 H18 Cl2 0.95 2.80 3.431(4) 125.0 1_565
C18 H18 Cl4 0.95 2.59 3.118(4) 115.0 .
C4 H4B Cl4 0.99 2.81 3.677(4) 146.7 1_545
C21 H21A Cl2 0.99 2.85 3.616(4) 135.2 1_565
C19 H19 Cl2 0.95 2.97 3.756(4) 140.5 3_666
C31 H31B Cl3 0.99 2.74 3.680(4) 159.7 4_575
C3 H3 Cl2 0.95 2.59 3.095(4) 113.7 .
C3 H3 Cl4 0.95 2.65 3.487(4) 146.7 1_545
C16 H16 Cl4 0.95 2.65 3.145(4) 113.3 .
C14 H14A Cl1 0.99 2.76 3.619(4) 145.7 4_566
C15 H15 Cl1 0.95 2.82 3.633(4) 144.1 3_766
C1A H1A Cl2 1.00 2.64 3.623(5) 168.7 3_666

_refine_diff_density_max         1.672
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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 1569711'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            2
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8 O0.58, 0.78(O)'
_chemical_formula_sum            'C34 H40 Cl4 Cu2 N8 O1.36'
_chemical_formula_weight         851.38

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                   8.333(4)
_cell_length_b                   10.394(5)
_cell_length_c                   22.167(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.264(7)
_cell_angle_gamma                90
_cell_volume                     1900.1(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4090
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      28.05

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             874
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.441
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7615
_exptl_absorpt_correction_T_max  0.8934
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11053
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.857
_diffrn_reflns_theta_max         28.045
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4090
_reflns_number_gt                3009
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+0.8537P] 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         4090
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.02126(4) 0.28596(4) 0.40498(2) 0.02037(12) Uani 1 1 d . . . . .
Cl1 Cl 0.15831(9) 0.31826(8) 0.32493(3) 0.02161(19) Uani 1 1 d . . . . .
N2 N 0.4039(3) 0.1644(3) 0.53055(11) 0.0179(6) Uani 1 1 d . . . . .
Cl2 Cl -0.12378(10) 0.15238(9) 0.45904(4) 0.0358(3) Uani 1 1 d . . . . .
N3 N 0.3363(3) 0.4999(2) 0.69622(11) 0.0156(6) Uani 1 1 d . . . . .
N1 N 0.2223(3) 0.2531(2) 0.46150(11) 0.0185(6) Uani 1 1 d . . . . .
C12 C 0.2587(4) 0.2228(3) 0.64615(14) 0.0203(7) Uani 1 1 d . . . . .
H12A H 0.227628 0.289824 0.615629 0.030 Uiso 1 1 calc R U . . .
H12B H 0.203013 0.237549 0.681586 0.030 Uiso 1 1 calc R U . . .
H12C H 0.227814 0.138322 0.628500 0.030 Uiso 1 1 calc R U . . .
N4 N 0.1749(3) 0.6278(2) 0.63604(11) 0.0169(6) Uani 1 1 d . . . . .
C6 C 0.7126(4) 0.1496(3) 0.65644(13) 0.0171(7) Uani 1 1 d . . . . .
C2 C 0.4742(4) 0.2719(3) 0.51006(15) 0.0265(8) Uani 1 1 d . . . . .
H2 H 0.581017 0.302248 0.523152 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4418(4) 0.2267(3) 0.66600(13) 0.0145(6) Uani 1 1 d . . . . .
C8 C 0.5064(4) 0.3087(3) 0.71382(13) 0.0153(7) Uani 1 1 d . . . . .
C3 C 0.2521(4) 0.1567(3) 0.50029(14) 0.0179(7) Uani 1 1 d . . . . .
H3 H 0.176620 0.090900 0.506065 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4771(4) 0.0758(3) 0.57918(13) 0.0203(7) Uani 1 1 d . . . . .
H4A H 0.565201 0.025980 0.564595 0.024 Uiso 1 1 calc R U . . .
H4B H 0.393927 0.014316 0.589088 0.024 Uiso 1 1 calc R U . . .
C16 C 0.1825(4) 0.5385(3) 0.67890(13) 0.0163(7) Uani 1 1 d . . . . .
H16 H 0.091323 0.505986 0.695279 0.020 Uiso 1 1 calc R U . . .
C1 C 0.3619(4) 0.3266(3) 0.46751(15) 0.0277(8) Uani 1 1 d . . . . .
H1 H 0.376750 0.402901 0.445401 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5447(4) 0.1508(3) 0.63603(13) 0.0149(7) Uani 1 1 d . . . . .
C17 C 0.7732(4) 0.2310(3) 0.70430(13) 0.0166(7) Uani 1 1 d . . . . .
H17 H 0.886420 0.230701 0.718236 0.020 Uiso 1 1 calc R U . . .
C9 C 0.6746(4) 0.3127(3) 0.73248(13) 0.0163(7) Uani 1 1 d . . . . .
C10 C 0.7529(4) 0.4049(3) 0.78120(14) 0.0212(7) Uani 1 1 d . . . . .
H10A H 0.870085 0.389612 0.788666 0.032 Uiso 1 1 calc R U . . .
H10B H 0.706999 0.390923 0.818975 0.032 Uiso 1 1 calc R U . . .
H10C H 0.732000 0.493692 0.767378 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3955(4) 0.3999(3) 0.74126(14) 0.0181(7) Uani 1 1 d . . . . .
H13A H 0.302463 0.351712 0.753194 0.022 Uiso 1 1 calc R U . . .
H13B H 0.455011 0.440513 0.778246 0.022 Uiso 1 1 calc R U . . .
C15 C 0.3325(4) 0.6470(3) 0.62585(14) 0.0203(7) Uani 1 1 d . . . . .
H15 H 0.365632 0.705713 0.597196 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8299(4) 0.0647(3) 0.62830(14) 0.0223(7) Uani 1 1 d . . . . .
H7A H 0.939200 0.074921 0.650878 0.033 Uiso 1 1 calc R U . . .
H7B H 0.830105 0.089559 0.585672 0.033 Uiso 1 1 calc R U . . .
H7C H 0.796195 -0.025406 0.630174 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4324(4) 0.5695(3) 0.66283(14) 0.0206(7) Uani 1 1 d . . . . .
H14 H 0.546986 0.564159 0.665305 0.025 Uiso 1 1 calc R U . . .
O1A O 0.1234(11) 0.6070(10) 0.4371(4) 0.082(3) Uani 0.39 1 d . . P A 1
O1B O 0.0438(14) 0.5106(12) 0.4724(5) 0.065(3) Uani 0.29 1 d . . P B -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.968(2) 3_566 ?
Cu1 N1 1.972(3) . ?
Cu1 Cl1 2.2688(12) . ?
Cu1 Cl2 2.2894(11) . ?
N2 C3 1.346(4) . ?
N2 C2 1.369(4) . ?
N2 C4 1.481(4) . ?
N3 C16 1.345(4) . ?
N3 C14 1.373(4) . ?
N3 C13 1.476(4) . ?
N1 C3 1.321(4) . ?
N1 C1 1.382(4) . ?
C12 C11 1.527(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N4 C16 1.323(4) . ?
N4 C15 1.379(4) . ?
C6 C17 1.393(4) . ?
C6 C5 1.407(4) . ?
C6 C7 1.517(4) . ?
C2 C1 1.354(4) . ?
C2 H2 0.9500 . ?
C11 C5 1.401(4) . ?
C11 C8 1.405(4) . ?
C8 C9 1.404(4) . ?
C8 C13 1.511(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.520(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C16 H16 0.9500 . ?
C1 H1 0.9500 . ?
C17 C9 1.390(4) . ?
C17 H17 0.9500 . ?
C9 C10 1.519(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C14 1.348(4) . ?
C15 H15 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 N1 160.97(11) 3_566 . ?
N4 Cu1 Cl1 92.83(8) 3_566 . ?
N1 Cu1 Cl1 92.59(8) . . ?
N4 Cu1 Cl2 92.99(8) 3_566 . ?
N1 Cu1 Cl2 91.54(8) . . ?
Cl1 Cu1 Cl2 149.55(4) . . ?
C3 N2 C2 107.4(3) . . ?
C3 N2 C4 125.8(3) . . ?
C2 N2 C4 126.7(3) . . ?
C16 N3 C14 107.1(3) . . ?
C16 N3 C13 128.0(3) . . ?
C14 N3 C13 124.9(3) . . ?
C3 N1 C1 106.3(3) . . ?
C3 N1 Cu1 127.4(2) . . ?
C1 N1 Cu1 126.3(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 N4 C15 105.7(2) . . ?
C16 N4 Cu1 127.0(2) . 3_566 ?
C15 N4 Cu1 127.3(2) . 3_566 ?
C17 C6 C5 118.3(3) . . ?
C17 C6 C7 118.8(3) . . ?
C5 C6 C7 122.8(3) . . ?
C1 C2 N2 106.7(3) . . ?
C1 C2 H2 126.6 . . ?
N2 C2 H2 126.6 . . ?
C5 C11 C8 120.3(3) . . ?
C5 C11 C12 120.2(3) . . ?
C8 C11 C12 119.5(3) . . ?
C9 C8 C11 119.9(3) . . ?
C9 C8 C13 120.4(3) . . ?
C11 C8 C13 119.6(3) . . ?
N1 C3 N2 110.7(3) . . ?
N1 C3 H3 124.6 . . ?
N2 C3 H3 124.6 . . ?
N2 C4 C5 110.5(3) . . ?
N2 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N4 C16 N3 111.1(3) . . ?
N4 C16 H16 124.5 . . ?
N3 C16 H16 124.5 . . ?
C2 C1 N1 108.8(3) . . ?
C2 C1 H1 125.6 . . ?
N1 C1 H1 125.6 . . ?
C11 C5 C6 120.0(3) . . ?
C11 C5 C4 120.2(3) . . ?
C6 C5 C4 119.7(3) . . ?
C9 C17 C6 122.7(3) . . ?
C9 C17 H17 118.7 . . ?
C6 C17 H17 118.7 . . ?
C17 C9 C8 118.6(3) . . ?
C17 C9 C10 118.9(3) . . ?
C8 C9 C10 122.4(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C13 C8 109.5(2) . . ?
N3 C13 H13A 109.8 . . ?
C8 C13 H13A 109.8 . . ?
N3 C13 H13B 109.8 . . ?
C8 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C14 C15 N4 109.5(3) . . ?
C14 C15 H15 125.3 . . ?
N4 C15 H15 125.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 C14 N3 106.6(3) . . ?
C15 C14 H14 126.7 . . ?
N3 C14 H14 126.7 . . ?

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 -0.1(4) . . . . ?
C4 N2 C2 C1 -177.3(3) . . . . ?
C5 C11 C8 C9 -1.2(4) . . . . ?
C12 C11 C8 C9 179.8(3) . . . . ?
C5 C11 C8 C13 173.7(3) . . . . ?
C12 C11 C8 C13 -5.2(4) . . . . ?
C1 N1 C3 N2 -0.3(4) . . . . ?
Cu1 N1 C3 N2 178.75(19) . . . . ?
C2 N2 C3 N1 0.3(4) . . . . ?
C4 N2 C3 N1 177.5(3) . . . . ?
C3 N2 C4 C5 -126.2(3) . . . . ?
C2 N2 C4 C5 50.5(4) . . . . ?
C15 N4 C16 N3 -0.2(3) . . . . ?
Cu1 N4 C16 N3 179.38(19) 3_566 . . . ?
C14 N3 C16 N4 0.6(3) . . . . ?
C13 N3 C16 N4 -178.0(3) . . . . ?
N2 C2 C1 N1 -0.1(4) . . . . ?
C3 N1 C1 C2 0.3(4) . . . . ?
Cu1 N1 C1 C2 -178.8(2) . . . . ?
C8 C11 C5 C6 4.3(4) . . . . ?
C12 C11 C5 C6 -176.7(3) . . . . ?
C8 C11 C5 C4 -171.9(3) . . . . ?
C12 C11 C5 C4 7.0(4) . . . . ?
C17 C6 C5 C11 -3.7(4) . . . . ?
C7 C6 C5 C11 176.8(3) . . . . ?
C17 C6 C5 C4 172.6(3) . . . . ?
C7 C6 C5 C4 -6.9(4) . . . . ?
N2 C4 C5 C11 60.6(4) . . . . ?
N2 C4 C5 C6 -115.6(3) . . . . ?
C5 C6 C17 C9 0.0(5) . . . . ?
C7 C6 C17 C9 179.6(3) . . . . ?
C6 C17 C9 C8 3.0(4) . . . . ?
C6 C17 C9 C10 -175.6(3) . . . . ?
C11 C8 C9 C17 -2.3(4) . . . . ?
C13 C8 C9 C17 -177.3(3) . . . . ?
C11 C8 C9 C10 176.2(3) . . . . ?
C13 C8 C9 C10 1.3(4) . . . . ?
C16 N3 C13 C8 130.2(3) . . . . ?
C14 N3 C13 C8 -48.2(4) . . . . ?
C9 C8 C13 N3 106.6(3) . . . . ?
C11 C8 C13 N3 -68.4(4) . . . . ?
C16 N4 C15 C14 -0.2(4) . . . . ?
Cu1 N4 C15 C14 -179.8(2) 3_566 . . . ?
N4 C15 C14 N3 0.6(4) . . . . ?
C16 N3 C14 C15 -0.7(3) . . . . ?
C13 N3 C14 C15 178.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 Cl2 0.95 2.65 3.134(3) 112.3 .
C3 H3 Cl2 0.95 2.70 3.543(4) 148.4 3_556
C4 H4B Cl2 0.99 2.92 3.780(4) 146.1 3_556
C13 H13A Cl1 0.99 2.76 3.680(3) 153.9 4_566
C15 H15 Cl2 0.95 2.66 3.158(3) 113.4 3_566
C14 H14 Cl1 0.95 2.72 3.578(4) 149.9 3_666

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1569717'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            8
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, 0.991(C6 H6)'
_chemical_formula_sum            'C39.95 H45.95 Cl4 Cu2 N8'
_chemical_formula_weight         907.07

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                   8.368(4)
_cell_length_b                   10.906(5)
_cell_length_c                   22.082(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.017(7)
_cell_angle_gamma                90
_cell_volume                     1990.2(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2586
_cell_measurement_theta_min      2.465
_cell_measurement_theta_max      26.4935

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             935.2
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    1.378
_shelx_estimated_absorpt_T_min   0.628
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_T_max  0.8554
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12010
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.868
_diffrn_reflns_theta_max         28.159
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4603
_reflns_number_gt                3483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.8732P] 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         4603
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.48143(4) 0.25644(3) 0.10438(2) 0.02037(12) Uani 1 1 d . . . . .
Cl1 Cl 0.34838(9) 0.29509(8) 0.18381(3) 0.0301(2) Uani 1 1 d . . . . .
Cl2 Cl 0.62610(10) 0.12780(9) 0.05433(4) 0.0421(3) Uani 1 1 d . . . . .
C5 C 0.9965(3) 0.6720(2) 0.21016(12) 0.0178(6) Uani 1 1 d . . . . .
N1 N 0.6752(3) 0.3472(2) 0.14359(11) 0.0207(5) Uani 1 1 d . . . . .
C11 C 1.0279(3) 0.8339(3) 0.13730(12) 0.0181(6) Uani 1 1 d . . . . .
N2 N 0.8328(3) 0.4834(2) 0.19675(11) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.6821(3) 0.4408(3) 0.18213(13) 0.0212(6) Uani 1 1 d . . . . .
H3 H 0.591084 0.473512 0.197467 0.025 Uiso 1 1 calc R U . . .
C6 C 1.1654(4) 0.6660(3) 0.22663(13) 0.0208(6) Uani 1 1 d . . . . .
C9 C 1.1970(3) 0.8305(3) 0.15485(13) 0.0199(6) Uani 1 1 d . . . . .
C12 C 0.9282(3) 0.7577(2) 0.16618(13) 0.0177(6) Uani 1 1 d . . . . .
C14 C 0.9552(4) 0.9200(3) 0.08627(13) 0.0281(7) Uani 1 1 d . . . . .
H14A H 0.869468 0.968924 0.101125 0.034 Uiso 1 1 calc R U . A 4
H14B H 1.040415 0.977722 0.077943 0.034 Uiso 1 1 calc R U . A 4
N3 N 0.8877(8) 0.8633(5) 0.0302(3) 0.0230(8) Uani 0.663(8) 1 d . . P B 4
C17 C 0.7347(13) 0.8572(10) 0.0029(4) 0.0230(8) Uani 0.663(8) 1 d . . P B 4
H17 H 0.646466 0.893197 0.018737 0.028 Uiso 0.663(8) 1 calc R U P B 4
C4 C 0.8892(4) 0.5844(3) 0.23892(13) 0.0239(7) Uani 1 1 d . . . . .
H4A H 0.950345 0.550514 0.277265 0.029 Uiso 1 1 calc R U . . .
H4B H 0.794643 0.629585 0.249476 0.029 Uiso 1 1 calc R U . . .
N4 N 0.7204(7) 0.7950(5) -0.0489(3) 0.0230(8) Uani 0.663(8) 1 d . . P B 4
C13 C 0.7459(4) 0.7671(3) 0.15091(15) 0.0271(7) Uani 1 1 d . . . . .
H13A H 0.716691 0.842467 0.127627 0.041 Uiso 1 1 calc R U . . .
H13B H 0.699235 0.768852 0.188942 0.041 Uiso 1 1 calc R U . . .
H13C H 0.703594 0.696070 0.126292 0.041 Uiso 1 1 calc R U . . .
C7 C 1.2481(4) 0.5756(3) 0.27348(15) 0.0325(8) Uani 1 1 d . . . . .
H7A H 1.365687 0.584437 0.276878 0.049 Uiso 1 1 calc R U . . .
H7B H 1.216770 0.491899 0.260462 0.049 Uiso 1 1 calc R U . . .
H7C H 1.215199 0.591902 0.313402 0.049 Uiso 1 1 calc R U . . .
C10 C 1.3101(4) 0.9144(3) 0.12775(15) 0.0286(7) Uani 1 1 d . . . . .
H10A H 1.421593 0.899005 0.147438 0.043 Uiso 1 1 calc R U . . .
H10B H 1.281511 0.999898 0.134567 0.043 Uiso 1 1 calc R U . . .
H10C H 1.300807 0.898939 0.083618 0.043 Uiso 1 1 calc R U . . .
C8 C 1.2610(4) 0.7471(3) 0.19937(14) 0.0219(6) Uani 1 1 d . . . . .
H8 H 1.374907 0.745232 0.211839 0.026 Uiso 1 1 calc R U . . .
C1 C 0.8310(4) 0.3287(3) 0.13421(17) 0.0335(8) Uani 1 1 d . . . . .
H1 H 0.865285 0.266946 0.108746 0.040 Uiso 1 1 calc R U . . .
C15 C 0.9791(6) 0.8015(5) -0.0058(2) 0.0230(8) Uani 0.663(8) 1 d . . P B 4
H15 H 1.093177 0.790662 0.001518 0.028 Uiso 0.663(8) 1 calc R U P B 4
C2 C 0.9292(4) 0.4124(3) 0.16703(17) 0.0333(8) Uani 1 1 d . . . . .
H2 H 1.042950 0.419871 0.168841 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8724(5) 0.7582(5) -0.0549(2) 0.0230(8) Uani 0.663(8) 1 d . . P B 4
H16 H 0.900326 0.710388 -0.087681 0.028 Uiso 0.663(8) 1 calc R U P B 4
C1A C 0.591(4) 0.530(2) 0.0237(12) 0.045(7) Uani 0.325(5) 1 d . . P C -1
H1A H 0.527934 0.559147 0.052928 0.054 Uiso 0.325(5) 1 calc R U P C -1
C2A C 0.7582(15) 0.5397(9) 0.0342(5) 0.034(3) Uani 0.325(5) 1 d . . P C -1
H2A H 0.810829 0.577597 0.070654 0.041 Uiso 0.325(5) 1 calc R U P C -1
C3A C 0.8489(13) 0.4945(9) -0.0080(5) 0.035(3) Uani 0.325(5) 1 d . . P C -1
H3A H 0.963442 0.501904 -0.000868 0.042 Uiso 0.325(5) 1 calc R U P C -1
C4A C 0.7706(12) 0.4380(9) -0.0612(5) 0.031(3) Uani 0.325(5) 1 d . . P C -1
H4A1 H 0.832600 0.405376 -0.089934 0.037 Uiso 0.325(5) 1 calc R U P C -1
C5A C 0.6127(14) 0.4292(10) -0.0719(5) 0.034(3) Uani 0.325(5) 1 d . . P C -1
H5A H 0.561408 0.389644 -0.108087 0.041 Uiso 0.325(5) 1 calc R U P C -1
C6A C 0.519(2) 0.4774(15) -0.0308(6) 0.036(3) Uani 0.325(5) 1 d . . P C -1
H6A H 0.404485 0.473876 -0.040220 0.043 Uiso 0.325(5) 1 calc R U P C -1
C3B C 0.6495(14) 0.4644(11) -0.0121(5) 0.041(3) Uani 0.341(8) 1 d . . P D 2
H3B H 0.753327 0.437849 -0.018937 0.049 Uiso 0.341(8) 1 calc R U P D 2
C1B C 0.4838(18) 0.5975(17) 0.0376(6) 0.049(4) Uani 0.341(8) 1 d . . P D 2
H1B H 0.475262 0.663162 0.065179 0.059 Uiso 0.341(8) 1 calc R U P D 2
C2B C 0.636(3) 0.564(2) 0.0230(12) 0.038(5) Uani 0.341(8) 1 d . . P D 2
H2B H 0.728789 0.611228 0.037950 0.045 Uiso 0.341(8) 1 calc R U P D 2
C16A C 0.8554(11) 0.6850(13) -0.0403(4) 0.030(2) Uani 0.337(8) 1 d . . P B 5
H16A H 0.869661 0.614566 -0.064218 0.036 Uiso 0.337(8) 1 calc R U P B 5
C15A C 0.9661(12) 0.7309(13) 0.0060(4) 0.030(2) Uani 0.337(8) 1 d . . P B 5
H15A H 1.071526 0.699703 0.019792 0.036 Uiso 0.337(8) 1 calc R U P B 5
N3A N 0.8955(16) 0.8318(12) 0.0291(6) 0.030(2) Uani 0.337(8) 1 d . . P B 5
N4A N 0.7171(15) 0.7591(10) -0.0466(5) 0.030(2) Uani 0.337(8) 1 d . . P B 5
C17A C 0.742(3) 0.845(2) -0.0023(9) 0.030(2) Uani 0.337(8) 1 d . . P B 5
H17A H 0.665713 0.904215 0.005888 0.036 Uiso 0.337(8) 1 calc R U P B 5


_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 N4A 1.937(11) 3_665 ?
Cu1 N1 1.980(2) . ?
Cu1 N4 2.005(6) 3_665 ?
Cu1 Cl2 2.2526(11) . ?
Cu1 Cl1 2.2596(12) . ?
C5 C12 1.403(4) . ?
C5 C6 1.404(4) . ?
C5 C4 1.517(4) . ?
N1 C3 1.324(4) . ?
N1 C1 1.367(4) . ?
C11 C12 1.400(4) . ?
C11 C9 1.407(4) . ?
C11 C14 1.519(4) . ?
N2 C3 1.336(4) . ?
N2 C2 1.359(4) . ?
N2 C4 1.472(4) . ?
C3 H3 0.9500 . ?
C6 C8 1.391(4) . ?
C6 C7 1.516(4) . ?
C9 C8 1.384(4) . ?
C9 C10 1.507(4) . ?
C12 C13 1.514(4) . ?
C14 N3 1.420(7) . ?
C14 N3A 1.603(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N3 C17 1.329(11) . ?
N3 C15 1.364(8) . ?
C17 N4 1.320(9) . ?
C17 H17 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N4 C16 1.360(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8 H8 0.9500 . ?
C1 C2 1.359(4) . ?
C1 H1 0.9500 . ?
C15 C16 1.376(6) . ?
C15 H15 0.9500 . ?
C2 H2 0.9500 . ?
C16 H16 0.9500 . ?
C1A C6A 1.38(3) . ?
C1A C2A 1.38(3) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.381(16) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.396(14) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.309(14) . ?
C4A H4A1 0.9500 . ?
C5A C6A 1.39(2) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C3B C2B 1.35(3) . ?
C3B C1B 1.348(18) 3_665 ?
C3B H3B 0.9500 . ?
C1B C2B 1.41(3) . ?
C1B H1B 0.9500 . ?
C2B H2B 0.9500 . ?
C16A C15A 1.363(12) . ?
C16A N4A 1.401(15) . ?
C16A H16A 0.9500 . ?
C15A N3A 1.383(14) . ?
C15A H15A 0.9500 . ?
N3A C17A 1.37(2) . ?
N4A C17A 1.343(19) . ?
C17A H17A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4A Cu1 N1 153.0(3) 3_665 . ?
N1 Cu1 N4 163.95(16) . 3_665 ?
N4A Cu1 Cl2 95.4(4) 3_665 . ?
N1 Cu1 Cl2 93.43(8) . . ?
N4 Cu1 Cl2 89.55(19) 3_665 . ?
N4A Cu1 Cl1 93.0(4) 3_665 . ?
N1 Cu1 Cl1 92.10(8) . . ?
N4 Cu1 Cl1 93.21(19) 3_665 . ?
Cl2 Cu1 Cl1 149.89(4) . . ?
C12 C5 C6 119.7(3) . . ?
C12 C5 C4 120.3(3) . . ?
C6 C5 C4 120.0(3) . . ?
C3 N1 C1 105.4(2) . . ?
C3 N1 Cu1 128.1(2) . . ?
C1 N1 Cu1 126.5(2) . . ?
C12 C11 C9 120.3(3) . . ?
C12 C11 C14 120.4(2) . . ?
C9 C11 C14 119.3(3) . . ?
C3 N2 C2 107.1(2) . . ?
C3 N2 C4 127.6(3) . . ?
C2 N2 C4 125.2(2) . . ?
N1 C3 N2 111.6(3) . . ?
N1 C3 H3 124.2 . . ?
N2 C3 H3 124.2 . . ?
C8 C6 C5 118.8(3) . . ?
C8 C6 C7 118.5(3) . . ?
C5 C6 C7 122.7(3) . . ?
C8 C9 C11 118.3(3) . . ?
C8 C9 C10 118.9(3) . . ?
C11 C9 C10 122.8(3) . . ?
C11 C12 C5 120.2(3) . . ?
C11 C12 C13 120.7(3) . . ?
C5 C12 C13 119.1(3) . . ?
N3 C14 C11 115.8(3) . . ?
C11 C14 N3A 104.6(5) . . ?
N3 C14 H14A 108.3 . . ?
C11 C14 H14A 108.3 . . ?
N3 C14 H14B 108.3 . . ?
C11 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C17 N3 C15 107.4(5) . . ?
C17 N3 C14 129.8(5) . . ?
C15 N3 C14 122.8(5) . . ?
N4 C17 N3 111.7(7) . . ?
N4 C17 H17 124.2 . . ?
N3 C17 H17 124.2 . . ?
N2 C4 C5 111.0(2) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C17 N4 C16 106.1(6) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C8 C6 122.7(3) . . ?
C9 C8 H8 118.7 . . ?
C6 C8 H8 118.7 . . ?
C2 C1 N1 109.3(3) . . ?
C2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?
N3 C15 C16 106.0(4) . . ?
N3 C15 H15 127.0 . . ?
C16 C15 H15 127.0 . . ?
N2 C2 C1 106.6(3) . . ?
N2 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
N4 C16 C15 108.9(5) . . ?
N4 C16 H16 125.6 . . ?
C15 C16 H16 125.6 . . ?
C6A C1A C2A 118(2) . . ?
C6A C1A H1A 121.1 . . ?
C2A C1A H1A 121.1 . . ?
C3A C2A C1A 120.5(15) . . ?
C3A C2A H2A 119.7 . . ?
C1A C2A H2A 119.7 . . ?
C2A C3A C4A 119.3(10) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
C5A C4A C3A 120.8(11) . . ?
C5A C4A H4A1 119.6 . . ?
C3A C4A H4A1 119.6 . . ?
C4A C5A C6A 120.7(11) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A C5A 120.8(18) . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C2B C3B H3B 119.9 . . ?
C1B C3B H3B 119.9 3_665 . ?
C3B C1B C2B 119.4(17) 3_665 . ?
C3B C1B H1B 120.3 3_665 . ?
C2B C1B H1B 120.3 . . ?
C3B C2B C1B 120.2(18) . . ?
C3B C2B H2B 119.9 . . ?
C1B C2B H2B 119.9 . . ?
C15A C16A N4A 108.4(9) . . ?
C15A C16A H16A 125.8 . . ?
N4A C16A H16A 125.8 . . ?
C16A C15A N3A 106.8(9) . . ?
C16A C15A H15A 126.6 . . ?
N3A C15A H15A 126.6 . . ?
C17A N3A C15A 108.4(10) . . ?
C17A N3A C14 119.3(9) . . ?
C15A N3A C14 132.0(9) . . ?
C17A N4A C16A 107.2(11) . . ?
N4A C17A N3A 109.0(13) . . ?
N4A C17A H17A 125.5 . . ?
N3A C17A H17A 125.5 . . ?

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 1.0(3) . . . . ?
Cu1 N1 C3 N2 -176.60(19) . . . . ?
C2 N2 C3 N1 -1.1(3) . . . . ?
C4 N2 C3 N1 -178.7(3) . . . . ?
C12 C5 C6 C8 1.0(4) . . . . ?
C4 C5 C6 C8 179.8(3) . . . . ?
C12 C5 C6 C7 -179.7(3) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C12 C11 C9 C8 2.4(4) . . . . ?
C14 C11 C9 C8 -176.9(3) . . . . ?
C12 C11 C9 C10 -176.9(3) . . . . ?
C14 C11 C9 C10 3.8(4) . . . . ?
C9 C11 C12 C5 -3.9(4) . . . . ?
C14 C11 C12 C5 175.4(3) . . . . ?
C9 C11 C12 C13 175.5(3) . . . . ?
C14 C11 C12 C13 -5.2(4) . . . . ?
C6 C5 C12 C11 2.2(4) . . . . ?
C4 C5 C12 C11 -176.5(2) . . . . ?
C6 C5 C12 C13 -177.3(3) . . . . ?
C4 C5 C12 C13 4.0(4) . . . . ?
C12 C11 C14 N3 -69.9(5) . . . . ?
C9 C11 C14 N3 109.4(4) . . . . ?
C12 C11 C14 N3A -71.9(6) . . . . ?
C9 C11 C14 N3A 107.4(6) . . . . ?
C11 C14 N3 C17 113.2(8) . . . . ?
C11 C14 N3 C15 -66.2(7) . . . . ?
C15 N3 C17 N4 0.0(10) . . . . ?
C14 N3 C17 N4 -179.5(6) . . . . ?
C3 N2 C4 C5 -132.3(3) . . . . ?
C2 N2 C4 C5 50.5(4) . . . . ?
C12 C5 C4 N2 77.4(3) . . . . ?
C6 C5 C4 N2 -101.4(3) . . . . ?
N3 C17 N4 C16 0.6(10) . . . . ?
N3 C17 N4 Cu1 173.6(5) . . . 3_665 ?
C11 C9 C8 C6 0.9(4) . . . . ?
C10 C9 C8 C6 -179.8(3) . . . . ?
C5 C6 C8 C9 -2.6(4) . . . . ?
C7 C6 C8 C9 178.0(3) . . . . ?
C3 N1 C1 C2 -0.5(4) . . . . ?
Cu1 N1 C1 C2 177.2(2) . . . . ?
C17 N3 C15 C16 -0.6(7) . . . . ?
C14 N3 C15 C16 178.9(5) . . . . ?
C3 N2 C2 C1 0.8(4) . . . . ?
C4 N2 C2 C1 178.5(3) . . . . ?
N1 C1 C2 N2 -0.2(4) . . . . ?
C17 N4 C16 C15 -0.9(7) . . . . ?
Cu1 N4 C16 C15 -174.3(4) 3_665 . . . ?
N3 C15 C16 N4 0.9(6) . . . . ?
C6A C1A C2A C3A -2(3) . . . . ?
C1A C2A C3A C4A -0.6(19) . . . . ?
C2A C3A C4A C5A 1.2(16) . . . . ?
C3A C4A C5A C6A 0.7(17) . . . . ?
C2A C1A C6A C5A 4(3) . . . . ?
C4A C5A C6A C1A -3(2) . . . . ?
C1B C3B C2B C1B 5(3) 3_665 . . . ?
C3B C1B C2B C3B -5(3) 3_665 . . . ?
N4A C16A C15A N3A 1.1(13) . . . . ?
C16A C15A N3A C17A 1.3(17) . . . . ?
C16A C15A N3A C14 175.0(12) . . . . ?
C11 C14 N3A C17A 130.8(15) . . . . ?
C11 C14 N3A C15A -42.3(16) . . . . ?
C15A C16A N4A C17A -3.2(17) . . . . ?
C15A C16A N4A Cu1 179.4(9) . . . 3_665 ?
C16A N4A C17A N3A 4(2) . . . . ?
Cu1 N4A C17A N3A -178.5(10) 3_665 . . . ?
C15A N3A C17A N4A -3(2) . . . . ?
C14 N3A C17A N4A -177.9(13) . . . . ?

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 H14A Cl2 0.99 2.75 3.551(4) 138.4 1_565
C17 H17 Cl2 0.95 2.69 3.339(9) 126.1 1_565
C17 H17 Cl2 0.95 2.59 3.089(11) 113.2 3_665
C4 H4B Cl1 0.99 2.72 3.634(3) 153.2 2_655
C1 H1 Cl2 0.95 2.65 3.147(3) 113.5 .
C15 H15 Cl2 0.95 2.96 3.710(5) 137.2 3_765
C2 H2 Cl1 0.95 2.87 3.698(4) 146.4 1_655
C16 H16 Cl1 0.95 2.73 3.194(5) 110.8 3_665
C17A H17A Cl2 0.95 2.70 3.53(2) 145.2 1_565
C17A H17A Cl2 0.95 2.61 3.13(2) 114.5 3_665

_refine_diff_density_max         0.779
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1569710'
_audit_update_record             
;
2017-08-18 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            11
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H40 Cl4 Cu2 N8, C6 H4 Cl2'
_chemical_formula_sum            'C40 H44 Cl6 Cu2 N8'
_chemical_formula_weight         976.61

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                   8.383(2)
_cell_length_b                   10.868(3)
_cell_length_c                   22.633(6)
_cell_angle_alpha                90
_cell_angle_beta                 79.007(3)
_cell_angle_gamma                90
_cell_volume                     2024.3(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4356
_cell_measurement_theta_min      1.83
_cell_measurement_theta_max      27.84

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.489
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6636
_exptl_absorpt_correction_T_max  0.8654
_exptl_absorpt_process_details   'SADABS, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11073
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         27.839
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4358
_reflns_number_gt                3474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+6.3087P] 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         4358
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.02840(6) 0.75114(5) 0.10483(2) 0.01528(14) Uani 1 1 d . . . . .
Cl2 Cl 0.15629(12) 0.71612(10) 0.18320(4) 0.0203(2) Uani 1 1 d . . . . .
Cl1 Cl -0.11710(12) 0.87989(10) 0.05680(5) 0.0267(3) Uani 1 1 d . . . . .
C5 C 0.5281(5) 0.8270(3) -0.13963(17) 0.0144(8) Uani 1 1 d . . . . .
N2 N 0.3977(4) 0.8590(3) -0.03227(15) 0.0150(7) Uani 1 1 d . . . . .
N1 N 0.2313(4) 0.7906(3) 0.04773(14) 0.0148(7) Uani 1 1 d . . . . .
N4 N 0.1676(4) 0.3395(3) -0.14452(14) 0.0157(7) Uani 1 1 d . . . . .
C8 C 0.4980(5) 0.6622(4) -0.21006(17) 0.0157(8) Uani 1 1 d . . . . .
C12 C 0.6977(5) 0.8217(4) -0.15808(17) 0.0149(8) Uani 1 1 d . . . . .
C3 C 0.2428(5) 0.8467(4) -0.00452(17) 0.0155(8) Uani 1 1 d . . . . .
H3 H 0.152376 0.874899 -0.020451 0.019 Uiso 1 1 calc R U . . .
C14 C 0.3906(5) 0.5769(4) -0.23847(18) 0.0182(9) Uani 1 1 d . . . . .
H14A H 0.296704 0.623861 -0.247330 0.022 Uiso 1 1 calc R U . . .
H14B H 0.452974 0.545210 -0.277037 0.022 Uiso 1 1 calc R U . . .
N3 N 0.3307(4) 0.4722(3) -0.19882(15) 0.0172(7) Uani 1 1 d . . . . .
C10 C 0.7518(5) 0.5620(4) -0.27257(19) 0.0235(9) Uani 1 1 d . . . . .
H10A H 0.869161 0.577362 -0.280366 0.035 Uiso 1 1 calc R U . . .
H10B H 0.710849 0.570610 -0.310117 0.035 Uiso 1 1 calc R U . . .
H10C H 0.730158 0.478459 -0.256780 0.035 Uiso 1 1 calc R U . . .
C2 C 0.4923(5) 0.8110(4) 0.00495(19) 0.0199(9) Uani 1 1 d . . . . .
H2 H 0.607581 0.807435 -0.002384 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4545(5) 0.9181(4) -0.09115(17) 0.0167(8) Uani 1 1 d . . . . .
H4A H 0.536678 0.981219 -0.086971 0.020 Uiso 1 1 calc R U . . .
H4B H 0.361751 0.960207 -0.103769 0.020 Uiso 1 1 calc R U . . .
C1 C 0.3887(5) 0.7694(4) 0.05456(19) 0.0213(9) Uani 1 1 d . . . . .
H1 H 0.419938 0.731728 0.088492 0.026 Uiso 1 1 calc R U . . .
C17 C 0.1755(5) 0.4382(4) -0.17923(18) 0.0168(8) Uani 1 1 d . . . . .
H17 H 0.083990 0.479380 -0.188965 0.020 Uiso 1 1 calc R U . . .
C9 C 0.6675(5) 0.6539(4) -0.22700(17) 0.0160(8) Uani 1 1 d . . . . .
C13 C 0.8128(5) 0.9065(4) -0.1338(2) 0.0236(10) Uani 1 1 d . . . . .
H13A H 0.924295 0.891012 -0.154926 0.035 Uiso 1 1 calc R U . . .
H13B H 0.804954 0.891362 -0.090671 0.035 Uiso 1 1 calc R U . . .
H13C H 0.783711 0.992237 -0.140098 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2436(5) 0.7574(4) -0.14863(18) 0.0200(9) Uani 1 1 d . . . . .
H7A H 0.194964 0.746719 -0.184391 0.030 Uiso 1 1 calc R U . . .
H7B H 0.213300 0.838162 -0.130667 0.030 Uiso 1 1 calc R U . . .
H7C H 0.203888 0.692780 -0.119309 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7636(5) 0.7343(4) -0.20113(18) 0.0182(9) Uani 1 1 d . . . . .
H11 H 0.878316 0.729529 -0.213190 0.022 Uiso 1 1 calc R U . . .
C15 C 0.4278(5) 0.3899(4) -0.17701(18) 0.0194(9) Uani 1 1 d . . . . .
H15 H 0.543154 0.389771 -0.183899 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3263(5) 0.3080(4) -0.14342(19) 0.0203(9) Uani 1 1 d . . . . .
H16 H 0.359451 0.239730 -0.122485 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4272(5) 0.7490(4) -0.16649(17) 0.0156(8) Uani 1 1 d . . . . .
Cl1A Cl 0.13694(17) 0.44570(14) 0.05336(6) 0.0448(3) Uani 1 1 d . . . . .
C1A C 0.3406(6) 0.4770(4) 0.0232(2) 0.0314(11) Uani 1 1 d . . . . .
C2A C 0.3830(6) 0.5160(4) -0.0357(2) 0.0290(11) Uani 1 1 d . . . . .
H2A H 0.302532 0.526392 -0.059713 0.035 Uiso 1 1 calc R U . . .
C3A C 0.4544(6) 0.4602(4) 0.0592(2) 0.0309(11) Uani 1 1 d . . . . .
H3A H 0.422023 0.432701 0.099598 0.037 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 N1 1.977(3) . ?
Cu1 N4 1.979(3) 3_565 ?
Cu1 Cl1 2.2656(12) . ?
Cu1 Cl2 2.2729(12) . ?
C5 C12 1.405(5) . ?
C5 C6 1.413(6) . ?
C5 C4 1.519(5) . ?
N2 C3 1.337(5) . ?
N2 C2 1.366(5) . ?
N2 C4 1.474(5) . ?
N1 C3 1.318(5) . ?
N1 C1 1.377(5) . ?
N4 C17 1.323(5) . ?
N4 C16 1.379(5) . ?
C8 C9 1.402(5) . ?
C8 C6 1.411(6) . ?
C8 C14 1.519(5) . ?
C12 C11 1.397(5) . ?
C12 C13 1.511(6) . ?
C3 H3 0.9500 . ?
C14 N3 1.476(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N3 C17 1.344(5) . ?
N3 C15 1.364(5) . ?
C10 C9 1.510(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C2 C1 1.359(6) . ?
C2 H2 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C1 H1 0.9500 . ?
C17 H17 0.9500 . ?
C9 C11 1.391(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C7 C6 1.518(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 H11 0.9500 . ?
C15 C16 1.359(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
Cl1A C1A 1.747(5) . ?
C1A C2A 1.380(7) . ?
C1A C3A 1.380(7) . ?
C2A C3A 1.390(7) 3_665 ?
C2A H2A 0.9500 . ?
C3A H3A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N4 160.26(13) . 3_565 ?
N1 Cu1 Cl1 91.57(10) . . ?
N4 Cu1 Cl1 92.81(10) 3_565 . ?
N1 Cu1 Cl2 94.09(10) . . ?
N4 Cu1 Cl2 92.10(10) 3_565 . ?
Cl1 Cu1 Cl2 148.77(5) . . ?
C12 C5 C6 120.2(4) . . ?
C12 C5 C4 119.3(3) . . ?
C6 C5 C4 120.5(3) . . ?
C3 N2 C2 107.4(3) . . ?
C3 N2 C4 125.8(3) . . ?
C2 N2 C4 126.8(3) . . ?
C3 N1 C1 105.7(3) . . ?
C3 N1 Cu1 126.4(3) . . ?
C1 N1 Cu1 127.9(3) . . ?
C17 N4 C16 105.8(3) . . ?
C17 N4 Cu1 128.1(3) . 3_565 ?
C16 N4 Cu1 126.0(3) . 3_565 ?
C9 C8 C6 120.2(4) . . ?
C9 C8 C14 119.8(4) . . ?
C6 C8 C14 120.0(4) . . ?
C11 C12 C5 118.5(4) . . ?
C11 C12 C13 118.3(4) . . ?
C5 C12 C13 123.2(4) . . ?
N1 C3 N2 111.5(4) . . ?
N1 C3 H3 124.3 . . ?
N2 C3 H3 124.3 . . ?
N3 C14 C8 111.9(3) . . ?
N3 C14 H14A 109.2 . . ?
C8 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C8 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C17 N3 C15 107.9(3) . . ?
C17 N3 C14 127.5(3) . . ?
C15 N3 C14 124.6(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C2 N2 106.4(4) . . ?
C1 C2 H2 126.8 . . ?
N2 C2 H2 126.8 . . ?
N2 C4 C5 112.7(3) . . ?
N2 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C2 C1 N1 109.0(4) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
N4 C17 N3 110.8(4) . . ?
N4 C17 H17 124.6 . . ?
N3 C17 H17 124.6 . . ?
C11 C9 C8 118.8(4) . . ?
C11 C9 C10 118.0(4) . . ?
C8 C9 C10 123.2(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C11 C12 122.5(4) . . ?
C9 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C16 C15 N3 106.2(4) . . ?
C16 C15 H15 126.9 . . ?
N3 C15 H15 126.9 . . ?
C15 C16 N4 109.3(4) . . ?
C15 C16 H16 125.4 . . ?
N4 C16 H16 125.4 . . ?
C8 C6 C5 119.6(4) . . ?
C8 C6 C7 119.7(4) . . ?
C5 C6 C7 120.6(4) . . ?
C2A C1A C3A 122.2(5) . . ?
C2A C1A Cl1A 119.3(4) . . ?
C3A C1A Cl1A 118.5(4) . . ?
C1A C2A C3A 118.7(4) . 3_665 ?
C1A C2A H2A 120.6 . . ?
C3A C2A H2A 120.6 3_665 . ?
C1A C3A C2A 119.1(5) . 3_665 ?
C1A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 3_665 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C5 C12 C11 -3.0(6) . . . . ?
C4 C5 C12 C11 177.7(3) . . . . ?
C6 C5 C12 C13 176.7(4) . . . . ?
C4 C5 C12 C13 -2.6(6) . . . . ?
C1 N1 C3 N2 2.0(4) . . . . ?
Cu1 N1 C3 N2 -179.8(3) . . . . ?
C2 N2 C3 N1 -1.7(5) . . . . ?
C4 N2 C3 N1 -179.5(3) . . . . ?
C9 C8 C14 N3 100.0(4) . . . . ?
C6 C8 C14 N3 -79.6(5) . . . . ?
C8 C14 N3 C17 124.4(4) . . . . ?
C8 C14 N3 C15 -57.7(5) . . . . ?
C3 N2 C2 C1 0.7(5) . . . . ?
C4 N2 C2 C1 178.5(4) . . . . ?
C3 N2 C4 C5 -111.4(4) . . . . ?
C2 N2 C4 C5 71.2(5) . . . . ?
C12 C5 C4 N2 -104.1(4) . . . . ?
C6 C5 C4 N2 76.6(5) . . . . ?
N2 C2 C1 N1 0.5(5) . . . . ?
C3 N1 C1 C2 -1.5(5) . . . . ?
Cu1 N1 C1 C2 -179.7(3) . . . . ?
C16 N4 C17 N3 -1.5(4) . . . . ?
Cu1 N4 C17 N3 -178.9(3) 3_565 . . . ?
C15 N3 C17 N4 1.6(5) . . . . ?
C14 N3 C17 N4 179.8(4) . . . . ?
C6 C8 C9 C11 -1.5(6) . . . . ?
C14 C8 C9 C11 179.0(4) . . . . ?
C6 C8 C9 C10 179.0(4) . . . . ?
C14 C8 C9 C10 -0.5(6) . . . . ?
C8 C9 C11 C12 1.2(6) . . . . ?
C10 C9 C11 C12 -179.3(4) . . . . ?
C5 C12 C11 C9 1.1(6) . . . . ?
C13 C12 C11 C9 -178.7(4) . . . . ?
C17 N3 C15 C16 -0.9(5) . . . . ?
C14 N3 C15 C16 -179.2(4) . . . . ?
N3 C15 C16 N4 0.0(5) . . . . ?
C17 N4 C16 C15 0.9(5) . . . . ?
Cu1 N4 C16 C15 178.3(3) 3_565 . . . ?
C9 C8 C6 C5 -0.5(6) . . . . ?
C14 C8 C6 C5 179.1(3) . . . . ?
C9 C8 C6 C7 179.9(4) . . . . ?
C14 C8 C6 C7 -0.6(5) . . . . ?
C12 C5 C6 C8 2.7(6) . . . . ?
C4 C5 C6 C8 -178.0(3) . . . . ?
C12 C5 C6 C7 -177.6(4) . . . . ?
C4 C5 C6 C7 1.7(5) . . . . ?
C3A C1A C2A C3A -0.4(8) . . . 3_665 ?
Cl1A C1A C2A C3A -179.6(4) . . . 3_665 ?
C2A C1A C3A C2A 0.4(8) . . . 3_665 ?
Cl1A C1A C3A C2A 179.6(4) . . . 3_665 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 Cl1 0.95 2.58 3.092(4) 114.1 .
C3 H3 Cl1 0.95 2.82 3.437(4) 123.4 3_575
C14 H14A Cl2 0.99 2.75 3.659(4) 152.1 4_575
C2 H2 Cl1 0.95 2.99 3.759(4) 139.3 1_655
C4 H4B Cl1 0.99 2.74 3.548(4) 138.7 3_575
C1 H1 Cl2 0.95 2.78 3.232(4) 110.4 .
C15 H15 Cl2 0.95 2.77 3.650(4) 153.8 3_665
C16 H16 Cl1 0.95 2.62 3.127(4) 113.6 3_565

_refine_diff_density_max         0.993
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.103

