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

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

data_CuPR1
_database_code_depnum_ccdc_archive 'CCDC 1589354'
_audit_update_record             
;
2018-08-18 deposited with the CCDC.
2018-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H50 Cl2 Cu N6 O12'
_chemical_formula_weight         1061.41

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   15.209(19)
_cell_length_b                   20.64(3)
_cell_length_c                   15.35(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.50(2)
_cell_angle_gamma                90
_cell_volume                     4754(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    795
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      16.85

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             2992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .07
_exptl_crystal_size_min          .06
_exptl_absorpt_coefficient_mu    0.644
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18979
_diffrn_reflns_av_unetI/netI     0.1272
_diffrn_reflns_av_R_equivalents  0.1751
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.668
_diffrn_reflns_theta_max         19.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.465
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.465
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.465
_reflns_number_total             4006
_reflns_number_gt                2352
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0711P)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         4006
_refine_ls_number_parameters     641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_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 0.92752(8) 0.79558(5) 0.84867(8) 0.0284(4) Uani 1 1 d . . . . .
C43 C 0.9393(6) 0.6015(5) 0.7671(6) 0.021(2) Uani 1 1 d . . . . .
C1 C 0.9786(7) 0.4043(5) 0.6131(7) 0.027(3) Uani 1 1 d . . . . .
C11 C 1.1528(7) 0.6083(5) 0.8946(7) 0.028(3) Uani 1 1 d . . . . .
N2 N 0.9620(5) 0.7178(3) 0.7821(5) 0.024(2) Uani 1 1 d . . . . .
O11 O 0.6540(5) 0.6483(3) 0.2153(5) 0.051(2) Uani 1 1 d . . . . .
N1 N 0.8463(5) 0.7278(4) 0.8947(5) 0.028(2) Uani 1 1 d . . . . .
O10 O 0.5175(6) 0.5971(4) 0.1750(5) 0.081(3) Uani 1 1 d . . . . .
C33 C 0.9711(7) 0.9150(4) 0.9491(7) 0.040(3) Uani 1 1 d . . . . .
H33A H 1.0006 0.9043 1.0083 0.048 Uiso 1 1 calc R U . . .
H33B H 0.9499 0.9593 0.9497 0.048 Uiso 1 1 calc R U . . .
C17 C 1.0370(7) 0.7120(5) 1.0406(6) 0.030(3) Uani 1 1 d . . . . .
H17 H 1.0293 0.7556 1.0529 0.036 Uiso 1 1 calc R U . . .
O1 O 0.9431(4) 0.4660(3) 0.5970(4) 0.0307(17) Uani 1 1 d . . . . .
C26 C 0.7076(6) 0.6993(5) 0.6850(6) 0.023(2) Uani 1 1 d . . . . .
O3 O 0.8001(4) 0.5618(3) 0.5757(4) 0.0272(17) Uani 1 1 d . . . . .
C15 C 1.0918(6) 0.6958(5) 0.9764(6) 0.027(3) Uani 1 1 d . . . . .
Cl3 Cl 0.8341(2) 0.88022(18) 0.1395(2) 0.0679(11) Uani 1 1 d . . . . .
C24 C 0.7594(7) 0.7514(4) 0.6601(6) 0.025(3) Uani 1 1 d . . . . .
C42 C 0.9206(6) 0.6613(5) 0.8031(6) 0.019(2) Uani 1 1 d . . . . .
C48 C 1.0008(6) 0.5998(5) 0.7070(6) 0.028(3) Uani 1 1 d . . . . .
H48 H 1.0142 0.5608 0.6818 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7870(7) 0.6256(5) 0.5973(6) 0.026(3) Uani 1 1 d . . . . .
C16 C 1.1000(6) 0.6270(5) 0.9595(6) 0.027(3) Uani 1 1 d . . . . .
C25 C 0.7218(7) 0.6356(5) 0.6531(6) 0.024(3) Uani 1 1 d . . . . .
C30 C 0.6681(7) 0.5835(5) 0.6757(6) 0.031(3) Uani 1 1 d . . . . .
H30 H 0.6783 0.5419 0.6563 0.038 Uiso 1 1 calc R U . . .
C27 C 0.6405(7) 0.7065(5) 0.7385(6) 0.032(3) Uani 1 1 d . . . . .
H27 H 0.6311 0.7472 0.7612 0.038 Uiso 1 1 calc R U . . .
C5 C 1.0943(6) 0.3379(5) 0.6979(6) 0.029(3) Uani 1 1 d . . . . .
H5 H 1.1438 0.3340 0.7421 0.035 Uiso 1 1 calc R U . . .
C41 C 0.8603(7) 0.6664(5) 0.8642(6) 0.025(3) Uani 1 1 d . . . . .
C40 C 0.8190(6) 0.6107(5) 0.8909(6) 0.025(3) Uani 1 1 d . . . . .
C39 C 0.7599(6) 0.6188(5) 0.9507(6) 0.034(3) Uani 1 1 d . . . . .
H39 H 0.7304 0.5832 0.9693 0.040 Uiso 1 1 calc R U . . .
C7 C 0.8815(6) 0.4765(4) 0.5182(6) 0.030(3) Uani 1 1 d . . . . .
H7A H 0.8283 0.4507 0.5186 0.036 Uiso 1 1 calc R U . . .
H7B H 0.9078 0.4643 0.4672 0.036 Uiso 1 1 calc R U . . .
C12 C 1.2008(6) 0.6529(5) 0.8557(6) 0.027(3) Uani 1 1 d . . . . .
H12 H 1.2379 0.6394 0.8168 0.033 Uiso 1 1 calc R U . . .
C38 C 0.7454(7) 0.6795(6) 0.9820(7) 0.044(3) Uani 1 1 d . . . . .
H38 H 0.7068 0.6851 1.0225 0.053 Uiso 1 1 calc R U . . .
C20 C 1.0562(6) 0.5812(5) 1.0060(6) 0.030(3) Uani 1 1 d . . . . .
H20 H 1.0614 0.5373 0.9942 0.036 Uiso 1 1 calc R U . . .
C47 C 1.0404(7) 0.6563(5) 0.6864(6) 0.031(3) Uani 1 1 d . . . . .
H47 H 1.0810 0.6559 0.6473 0.037 Uiso 1 1 calc R U . . .
C45 C 0.8392(6) 0.5494(4) 0.8525(6) 0.028(3) Uani 1 1 d . . . . .
H45 H 0.8116 0.5120 0.8681 0.033 Uiso 1 1 calc R U . . .
C10 C 0.8579(7) 0.5487(4) 0.5143(6) 0.035(3) Uani 1 1 d . . . . .
H10A H 0.9118 0.5744 0.5285 0.042 Uiso 1 1 calc R U . . .
H10B H 0.8289 0.5601 0.4552 0.042 Uiso 1 1 calc R U . . .
C23 C 0.8171(6) 0.7401(5) 0.6013(7) 0.031(3) Uani 1 1 d . . . . .
H23 H 0.8478 0.7750 0.5824 0.037 Uiso 1 1 calc R U . . .
C8 C 1.1691(7) 0.4528(4) 0.7774(6) 0.033(3) Uani 1 1 d . . . . .
H8A H 1.2133 0.4330 0.7470 0.039 Uiso 1 1 calc R U . . .
H8B H 1.1647 0.4271 0.8295 0.039 Uiso 1 1 calc R U . . .
C36 C 0.7514(7) 0.8206(4) 0.6962(7) 0.038(3) Uani 1 1 d . . . . .
H36A H 0.7242 0.8485 0.6483 0.046 Uiso 1 1 calc R U . . .
H36B H 0.7125 0.8198 0.7402 0.046 Uiso 1 1 calc R U . . .
C34 C 1.0376(7) 0.9094(4) 0.8848(6) 0.038(3) Uani 1 1 d . . . . .
H34A H 1.0138 0.9303 0.8294 0.045 Uiso 1 1 calc R U . . .
H34B H 1.0932 0.9304 0.9093 0.045 Uiso 1 1 calc R U . . .
C18 C 0.9960(7) 0.6672(6) 1.0843(6) 0.038(3) Uani 1 1 d . . . . .
H18 H 0.9607 0.6802 1.1252 0.045 Uiso 1 1 calc R U . . .
C6 C 1.0535(7) 0.3986(5) 0.6783(7) 0.028(3) Uani 1 1 d . . . . .
C44 C 0.8961(7) 0.5453(5) 0.7956(6) 0.030(3) Uani 1 1 d . . . . .
H44 H 0.9083 0.5049 0.7737 0.036 Uiso 1 1 calc R U . . .
C2 C 0.9423(6) 0.3494(5) 0.5657(6) 0.030(3) Uani 1 1 d . . . . .
H2 H 0.8923 0.3531 0.5220 0.036 Uiso 1 1 calc R U . . .
C14 C 1.1383(7) 0.7410(4) 0.9306(6) 0.026(3) Uani 1 1 d . . . . .
C35 C 1.1253(7) 0.8133(4) 0.9395(6) 0.035(3) Uani 1 1 d . . . . .
H35A H 1.1102 0.8224 0.9972 0.042 Uiso 1 1 calc R U . . .
H35B H 1.1808 0.8353 0.9355 0.042 Uiso 1 1 calc R U . . .
C9 C 1.1965(7) 0.5213(4) 0.8040(6) 0.035(3) Uani 1 1 d . . . . .
H9A H 1.2599 0.5227 0.8269 0.041 Uiso 1 1 calc R U . . .
H9B H 1.1847 0.5496 0.7531 0.041 Uiso 1 1 calc R U . . .
C32 C 0.8218(6) 0.9119(4) 0.7760(6) 0.032(3) Uani 1 1 d . . . . .
H32A H 0.7676 0.9309 0.7441 0.038 Uiso 1 1 calc R U . . .
H32B H 0.8707 0.9415 0.7725 0.038 Uiso 1 1 calc R U . . .
C3 C 0.9829(8) 0.2892(5) 0.5859(8) 0.044(3) Uani 1 1 d . . . . .
H3 H 0.9586 0.2524 0.5561 0.052 Uiso 1 1 calc R U . . .
C19 C 1.0070(7) 0.6000(5) 1.0672(7) 0.034(3) Uani 1 1 d . . . . .
H19 H 0.9803 0.5690 1.0983 0.041 Uiso 1 1 calc R U . . .
C31 C 0.8126(7) 0.9013(4) 0.8717(7) 0.036(3) Uani 1 1 d . . . . .
H31A H 0.8028 0.9426 0.8986 0.043 Uiso 1 1 calc R U . . .
H31B H 0.7610 0.8741 0.8744 0.043 Uiso 1 1 calc R U . . .
C37 C 0.7888(7) 0.7330(4) 0.9525(6) 0.028(3) Uani 1 1 d . . . . .
H37 H 0.7777 0.7739 0.9738 0.033 Uiso 1 1 calc R U . . .
C29 C 0.6019(7) 0.5930(5) 0.7251(7) 0.042(3) Uani 1 1 d . . . . .
H29 H 0.5659 0.5587 0.7369 0.050 Uiso 1 1 calc R U . . .
C46 C 1.0190(6) 0.7148(5) 0.7249(6) 0.029(3) Uani 1 1 d . . . . .
H46 H 1.0457 0.7529 0.7099 0.035 Uiso 1 1 calc R U . . .
C22 C 0.8314(6) 0.6769(5) 0.5685(6) 0.028(3) Uani 1 1 d . . . . .
H22 H 0.8702 0.6707 0.5283 0.033 Uiso 1 1 calc R U . . .
C4 C 1.0588(8) 0.2831(5) 0.6494(8) 0.041(3) Uani 1 1 d . . . . .
H4 H 1.0862 0.2430 0.6600 0.050 Uiso 1 1 calc R U . . .
C28 C 0.5892(7) 0.6557(6) 0.7579(7) 0.045(3) Uani 1 1 d . . . . .
H28 H 0.5456 0.6625 0.7929 0.054 Uiso 1 1 calc R U . . .
C13 C 1.1935(6) 0.7181(5) 0.8749(6) 0.030(3) Uani 1 1 d . . . . .
H13 H 1.2273 0.7477 0.8489 0.036 Uiso 1 1 calc R U . . .
N3 N 0.8932(6) 0.8700(3) 0.9224(5) 0.031(2) Uani 1 1 d . . . . .
H3A H 0.8768 0.8517 0.9763 0.037 Uiso 1 1 calc R U . . .
N4 N 0.8391(5) 0.8485(3) 0.7364(5) 0.028(2) Uani 1 1 d . . . . .
H4A H 0.8740 0.8563 0.6892 0.034 Uiso 1 1 calc R U . . .
N5 N 1.0533(5) 0.8392(3) 0.8698(5) 0.025(2) Uani 1 1 d . . . . .
H5A H 1.0760 0.8363 0.8138 0.029 Uiso 1 1 calc R U . . .
O2 O 1.1464(4) 0.5428(3) 0.8713(4) 0.0307(17) Uani 1 1 d . . . . .
O4 O 0.8909(5) 0.8307(3) 0.1060(4) 0.059(2) Uani 1 1 d . . . . .
O5 O 0.8443(6) 0.9449(4) 0.0923(6) 0.098(3) Uani 1 1 d . . . . .
O7 O 0.8620(5) 0.8875(4) 0.2307(5) 0.069(3) Uani 1 1 d . . . . .
O6 O 0.7436(6) 0.8625(4) 0.1164(6) 0.092(3) Uani 1 1 d . . . . .
Cl1 Cl 0.5919(2) 0.62135(14) 0.14286(19) 0.0467(8) Uani 1 1 d . . . . .
O9 O 0.6340(5) 0.5754(3) 0.0955(4) 0.050(2) Uani 1 1 d . . . . .
O8 O 0.5610(6) 0.6750(4) 0.0800(5) 0.084(3) Uani 1 1 d . . . . .
O12 O 1.0840(4) 0.4546(3) 0.7201(4) 0.0342(18) Uani 1 1 d . . . . .
N1A N 0.6788(7) 0.4460(5) -0.0586(7) 0.060(3) Uani 1 1 d . . . . .
C1A C 0.5728(8) 0.4234(5) 0.0566(7) 0.065(4) Uani 1 1 d . . . . .
H1A1 H 0.6012 0.3934 0.1002 0.097 Uiso 1 1 calc R U . . .
H1A2 H 0.5177 0.4053 0.0272 0.097 Uiso 1 1 calc R U . . .
H1A3 H 0.5611 0.4633 0.0849 0.097 Uiso 1 1 calc R U . . .
C2A C 0.6318(9) 0.4361(5) -0.0084(8) 0.048(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.019(7) . ?
Cu1 N3 2.027(7) . ?
Cu1 N1 2.066(7) . ?
Cu1 N5 2.091(7) . ?
Cu1 N4 2.282(8) . ?
C43 C42 1.401(12) . ?
C43 C48 1.418(12) . ?
C43 C44 1.436(12) . ?
C1 O1 1.389(11) . ?
C1 C6 1.392(13) . ?
C1 C2 1.409(12) . ?
C11 C12 1.371(12) . ?
C11 O2 1.399(10) . ?
C11 C16 1.432(12) . ?
N2 C46 1.334(10) . ?
N2 C42 1.387(10) . ?
O11 Cl1 1.446(7) . ?
N1 C37 1.350(11) . ?
N1 C41 1.380(10) . ?
O10 Cl1 1.401(8) . ?
C33 N3 1.508(11) . ?
C33 C34 1.530(12) . ?
C17 C18 1.354(12) . ?
C17 C15 1.432(12) . ?
O1 C7 1.419(10) . ?
C26 C27 1.419(12) . ?
C26 C24 1.422(12) . ?
C26 C25 1.432(12) . ?
O3 C21 1.382(10) . ?
O3 C10 1.417(10) . ?
C15 C14 1.425(12) . ?
C15 C16 1.452(12) . ?
Cl3 O7 1.403(7) . ?
Cl3 O6 1.412(8) . ?
Cl3 O4 1.484(7) . ?
Cl3 O5 1.539(8) . ?
C24 C23 1.379(12) . ?
C24 C36 1.545(12) . ?
C42 C41 1.419(12) . ?
C48 C47 1.374(12) . ?
C21 C22 1.368(12) . ?
C21 C25 1.428(12) . ?
C16 C20 1.416(12) . ?
C25 C30 1.427(12) . ?
C30 C29 1.371(12) . ?
C27 C28 1.369(12) . ?
C5 C6 1.408(12) . ?
C5 C4 1.410(13) . ?
C41 C40 1.404(12) . ?
C40 C39 1.398(12) . ?
C40 C45 1.448(12) . ?
C39 C38 1.373(12) . ?
C7 C10 1.531(11) . ?
C12 C13 1.386(12) . ?
C38 C37 1.399(12) . ?
C20 C19 1.350(12) . ?
C47 C46 1.406(12) . ?
C45 C44 1.331(12) . ?
C23 C22 1.429(12) . ?
C8 O12 1.439(10) . ?
C8 C9 1.511(11) . ?
C36 N4 1.490(11) . ?
C34 N5 1.492(10) . ?
C18 C19 1.428(12) . ?
C6 O12 1.368(10) . ?
C2 C3 1.401(13) . ?
C14 C13 1.377(12) . ?
C14 C35 1.513(12) . ?
C35 N5 1.497(11) . ?
C9 O2 1.451(10) . ?
C32 N4 1.485(10) . ?
C32 C31 1.515(12) . ?
C3 C4 1.388(14) . ?
C31 N3 1.486(11) . ?
C29 C28 1.414(13) . ?
Cl1 O9 1.412(6) . ?
Cl1 O8 1.493(8) . ?
N1A C2A 1.152(13) . ?
C1A C2A 1.472(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 176.3(3) . . ?
N2 Cu1 N1 81.6(3) . . ?
N3 Cu1 N1 95.7(3) . . ?
N2 Cu1 N5 96.5(3) . . ?
N3 Cu1 N5 84.3(3) . . ?
N1 Cu1 N5 145.3(3) . . ?
N2 Cu1 N4 99.7(3) . . ?
N3 Cu1 N4 83.4(3) . . ?
N1 Cu1 N4 105.7(3) . . ?
N5 Cu1 N4 108.7(3) . . ?
C42 C43 C48 118.5(9) . . ?
C42 C43 C44 117.3(9) . . ?
C48 C43 C44 124.2(9) . . ?
O1 C1 C6 117.0(9) . . ?
O1 C1 C2 122.5(10) . . ?
C6 C1 C2 120.4(10) . . ?
C12 C11 O2 123.8(9) . . ?
C12 C11 C16 121.5(9) . . ?
O2 C11 C16 114.6(9) . . ?
C46 N2 C42 119.0(8) . . ?
C46 N2 Cu1 128.4(7) . . ?
C42 N2 Cu1 112.6(6) . . ?
C37 N1 C41 116.7(8) . . ?
C37 N1 Cu1 131.3(6) . . ?
C41 N1 Cu1 111.8(6) . . ?
N3 C33 C34 110.5(8) . . ?
C18 C17 C15 123.4(9) . . ?
C1 O1 C7 118.3(7) . . ?
C27 C26 C24 124.0(10) . . ?
C27 C26 C25 117.2(9) . . ?
C24 C26 C25 118.8(9) . . ?
C21 O3 C10 118.1(7) . . ?
C14 C15 C17 125.4(10) . . ?
C14 C15 C16 119.2(9) . . ?
C17 C15 C16 115.4(9) . . ?
O7 Cl3 O6 113.6(5) . . ?
O7 Cl3 O4 108.8(5) . . ?
O6 Cl3 O4 109.5(5) . . ?
O7 Cl3 O5 109.9(5) . . ?
O6 Cl3 O5 106.0(5) . . ?
O4 Cl3 O5 108.9(5) . . ?
C23 C24 C26 119.3(9) . . ?
C23 C24 C36 119.1(9) . . ?
C26 C24 C36 121.6(9) . . ?
N2 C42 C43 121.3(9) . . ?
N2 C42 C41 117.4(9) . . ?
C43 C42 C41 121.4(9) . . ?
C47 C48 C43 119.3(9) . . ?
C22 C21 O3 124.2(9) . . ?
C22 C21 C25 120.8(9) . . ?
O3 C21 C25 115.1(9) . . ?
C20 C16 C11 122.4(10) . . ?
C20 C16 C15 120.1(9) . . ?
C11 C16 C15 117.5(9) . . ?
C30 C25 C21 121.3(9) . . ?
C30 C25 C26 118.9(9) . . ?
C21 C25 C26 119.7(9) . . ?
C29 C30 C25 122.0(9) . . ?
C28 C27 C26 122.5(9) . . ?
C6 C5 C4 118.9(10) . . ?
N1 C41 C40 123.5(9) . . ?
N1 C41 C42 116.4(9) . . ?
C40 C41 C42 120.1(9) . . ?
C39 C40 C41 117.5(9) . . ?
C39 C40 C45 125.1(10) . . ?
C41 C40 C45 117.4(9) . . ?
C38 C39 C40 119.8(9) . . ?
O1 C7 C10 107.4(7) . . ?
C11 C12 C13 119.4(9) . . ?
C39 C38 C37 119.7(10) . . ?
C19 C20 C16 121.3(9) . . ?
C48 C47 C46 119.5(9) . . ?
C44 C45 C40 121.8(9) . . ?
O3 C10 C7 109.0(7) . . ?
C24 C23 C22 122.4(8) . . ?
O12 C8 C9 108.7(8) . . ?
N4 C36 C24 112.8(8) . . ?
N5 C34 C33 108.3(7) . . ?
C17 C18 C19 119.6(9) . . ?
O12 C6 C1 116.1(9) . . ?
O12 C6 C5 123.3(10) . . ?
C1 C6 C5 120.6(9) . . ?
C45 C44 C43 121.9(9) . . ?
C3 C2 C1 118.6(10) . . ?
C13 C14 C15 118.9(9) . . ?
C13 C14 C35 119.8(9) . . ?
C15 C14 C35 121.2(9) . . ?
N5 C35 C14 112.3(7) . . ?
O2 C9 C8 108.9(7) . . ?
N4 C32 C31 108.7(7) . . ?
C4 C3 C2 121.3(10) . . ?
C20 C19 C18 120.2(9) . . ?
N3 C31 C32 111.7(8) . . ?
N1 C37 C38 122.8(9) . . ?
C30 C29 C28 118.9(9) . . ?
N2 C46 C47 122.4(9) . . ?
C21 C22 C23 118.7(9) . . ?
C3 C4 C5 120.0(9) . . ?
C27 C28 C29 120.5(9) . . ?
C14 C13 C12 123.0(9) . . ?
C31 N3 C33 114.7(7) . . ?
C31 N3 Cu1 107.6(5) . . ?
C33 N3 Cu1 110.9(6) . . ?
C32 N4 C36 107.7(7) . . ?
C32 N4 Cu1 103.6(5) . . ?
C36 N4 Cu1 120.3(5) . . ?
C34 N5 C35 110.7(7) . . ?
C34 N5 Cu1 106.0(5) . . ?
C35 N5 Cu1 119.9(6) . . ?
C11 O2 C9 117.1(7) . . ?
O10 Cl1 O9 113.8(5) . . ?
O10 Cl1 O11 109.3(5) . . ?
O9 Cl1 O11 111.1(4) . . ?
O10 Cl1 O8 107.8(5) . . ?
O9 Cl1 O8 106.7(4) . . ?
O11 Cl1 O8 108.0(5) . . ?
C6 O12 C8 117.8(7) . . ?
N1A C2A C1A 179.3(14) . . ?

_refine_diff_density_max         1.133
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.076

_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_THETM01_CuPR1               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Caused by weakly diffracting thin crystal resulting in very
few spot at larger Bragg?s angle. Despite of long exposure times, the crystal
did not exhibit observable intensity to a higher resolution. The situation did
not improve even after recrystallisation and full set of fresh data collection.
The data were collected to a completeness that allows for confirmation of the
structure.
;
_vrf_REFNR01_CuPR1               
;
PROBLEM: Ratio of reflections to parameters is < 8 for a
RESPONSE: Caused by weakly diffracting thin crystal resulting in
very few spot at larger Bragg?s angle.
;
_vrf_PLAT088_CuPR1               
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.25 Note  
RESPONSE:Caused by weakly diffracting thin crystal resulting in
very few spot at larger Bragg?s angle.
;
# end Validation Reply Form

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

data_CuPR2
_database_code_depnum_ccdc_archive 'CCDC 1589356'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H54 Cl2 Cu N6 O12'
_chemical_formula_weight         1065.44

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.309(4)
_cell_length_b                   13.829(4)
_cell_length_c                   14.593(5)
_cell_angle_alpha                78.351(4)
_cell_angle_beta                 67.456(4)
_cell_angle_gamma                87.227(4)
_cell_volume                     2428.3(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3604
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      22.46

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             1066
_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    0.627
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24929
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.504
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9827
_reflns_number_gt                6194
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0651P)²+0.1000P] 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
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9827
_refine_ls_number_parameters     644
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_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 0.19156(3) 0.30802(3) 0.29391(3) 0.02124(13) Uani 1 1 d . . . . .
Cl1 Cl 0.53415(8) 0.72356(8) 0.56471(7) 0.0371(3) Uani 1 1 d . . . . .
N5 N 0.2746(2) 0.20810(19) 0.21455(19) 0.0191(6) Uani 1 1 d . . . . .
O3 O 0.11171(18) -0.07464(17) 0.17254(16) 0.0240(5) Uani 1 1 d . . . . .
O4 O 0.16059(19) -0.02633(17) -0.04648(17) 0.0282(6) Uani 1 1 d . . . . .
O2 O 0.40363(19) 0.27191(18) -0.16568(18) 0.0297(6) Uani 1 1 d . . . . .
C13 C 0.1537(3) 0.0036(2) 0.3806(2) 0.0203(7) Uani 1 1 d . . . . .
N1 N 0.1626(2) 0.2178(2) 0.43728(19) 0.0211(6) Uani 1 1 d . . . . .
H1 H 0.2290 0.1821 0.4338 0.025 Uiso 1 1 calc R U . . .
C46 C 0.3592(3) 0.1587(2) 0.2273(2) 0.0220(7) Uani 1 1 d . . . . .
H41 H 0.3831 0.1731 0.2753 0.026 Uiso 1 1 calc R U . . .
C30 C 0.4715(3) 0.3487(2) 0.0309(2) 0.0223(7) Uani 1 1 d . . . . .
C11 C 0.0057(3) 0.0953(2) 0.3506(2) 0.0224(8) Uani 1 1 d . . . . .
H51 H -0.0473 0.1423 0.3666 0.027 Uiso 1 1 calc R U . . .
O1 O 0.26992(19) 0.12399(18) -0.18577(17) 0.0287(6) Uani 1 1 d . . . . .
N4 N 0.1098(2) 0.3124(2) 0.19763(19) 0.0205(6) Uani 1 1 d . . . . .
C24 C 0.3789(3) 0.4701(2) 0.1483(2) 0.0249(8) Uani 1 1 d . . . . .
H50A H 0.4507 0.4942 0.1373 0.030 Uiso 1 1 calc R U . . .
H50B H 0.3339 0.5270 0.1451 0.030 Uiso 1 1 calc R U . . .
C19 C 0.0701(3) 0.1434(3) 0.4748(2) 0.0250(8) Uani 1 1 d . . . . .
H20A H 0.0022 0.1779 0.4911 0.030 Uiso 1 1 calc R U . . .
H20B H 0.0692 0.1007 0.5367 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0108(3) 0.0414(2) 0.2768(2) 0.0218(7) Uani 1 1 d . . . . .
H18 H -0.0389 0.0523 0.2454 0.026 Uiso 1 1 calc R U . . .
N2 N 0.1084(2) 0.4102(2) 0.3762(2) 0.0256(7) Uani 1 1 d . . . . .
H2 H 0.0444 0.4281 0.3594 0.031 Uiso 1 1 calc R U . . .
C26 C 0.3195(3) 0.4420(3) 0.0139(3) 0.0255(8) Uani 1 1 d . . . . .
H33 H 0.2679 0.4895 0.0333 0.031 Uiso 1 1 calc R U . . .
Cl2 Cl 0.99532(7) 0.35550(6) 0.78020(6) 0.0286(2) Uani 1 1 d . . . . .
O5 O 0.5945(2) 0.6544(2) 0.5032(2) 0.0481(8) Uani 1 1 d . . . . .
O6 O 0.6078(2) 0.8003(2) 0.5586(3) 0.0625(9) Uani 1 1 d . . . . .
O8 O 0.4847(3) 0.6726(3) 0.6677(2) 0.0693(11) Uani 1 1 d . . . . .
O9 O 1.0501(2) 0.43886(18) 0.70081(18) 0.0359(6) Uani 1 1 d . . . . .
O11 O 0.9420(2) 0.29461(19) 0.7422(2) 0.0436(7) Uani 1 1 d . . . . .
O12 O 0.9166(2) 0.3916(2) 0.86487(19) 0.0438(7) Uani 1 1 d . . . . .
C2 C 0.2656(3) 0.0391(3) -0.2186(3) 0.0256(8) Uani 1 1 d . . . . .
C4 C 0.2027(3) -0.1320(3) -0.1712(3) 0.0310(9) Uani 1 1 d . . . . .
H4 H 0.1635 -0.1854 -0.1223 0.037 Uiso 1 1 calc R U . . .
C3 C 0.2086(3) -0.0420(3) -0.1445(3) 0.0251(8) Uani 1 1 d . . . . .
C1 C 0.3156(3) 0.0279(3) -0.3185(3) 0.0332(9) Uani 1 1 d . . . . .
H1A H 0.3520 0.0816 -0.3685 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3118(3) -0.0628(3) -0.3445(3) 0.0385(10) Uani 1 1 d . . . . .
H6 H 0.3472 -0.0696 -0.4114 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2564(3) -0.1419(3) -0.2724(3) 0.0372(10) Uani 1 1 d . . . . .
H5 H 0.2541 -0.2023 -0.2903 0.045 Uiso 1 1 calc R U . . .
C7 C 0.0881(3) -0.1030(3) 0.0274(2) 0.0256(8) Uani 1 1 d . . . . .
H8A H 0.1282 -0.1617 0.0383 0.031 Uiso 1 1 calc R U . . .
H8B H 0.0332 -0.1198 0.0043 0.031 Uiso 1 1 calc R U . . .
C36 C 0.3257(3) 0.2074(3) -0.2631(3) 0.0334(9) Uani 1 1 d . . . . .
H9A H 0.2893 0.2255 -0.3101 0.040 Uiso 1 1 calc R U . . .
H9B H 0.4001 0.1912 -0.3006 0.040 Uiso 1 1 calc R U . . .
C8 C 0.0355(3) -0.0654(3) 0.1238(3) 0.0261(8) Uani 1 1 d . . . . .
H7A H 0.0170 0.0032 0.1094 0.031 Uiso 1 1 calc R U . . .
H7B H -0.0307 -0.1038 0.1674 0.031 Uiso 1 1 calc R U . . .
C35 C 0.3248(3) 0.2913(3) -0.2122(3) 0.0296(8) Uani 1 1 d . . . . .
H10A H 0.3435 0.3530 -0.2613 0.035 Uiso 1 1 calc R U . . .
H10B H 0.2530 0.2964 -0.1612 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2944(3) -0.1565(3) 0.3452(3) 0.0308(9) Uani 1 1 d . . . . .
H13 H 0.3399 -0.2098 0.3348 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1587(3) -0.0516(2) 0.3068(2) 0.0200(7) Uani 1 1 d . . . . .
C17 C 0.2926(3) -0.1006(3) 0.4159(3) 0.0320(9) Uani 1 1 d . . . . .
H12 H 0.3384 -0.1159 0.4512 0.038 Uiso 1 1 calc R U . . .
C9 C 0.0893(3) -0.0269(2) 0.2516(2) 0.0202(7) Uani 1 1 d . . . . .
C15 C 0.2288(3) -0.1322(3) 0.2910(2) 0.0241(8) Uani 1 1 d . . . . .
H14 H 0.2305 -0.1691 0.2438 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2235(3) -0.0235(3) 0.4335(2) 0.0265(8) Uani 1 1 d . . . . .
H11 H 0.2226 0.0119 0.4815 0.032 Uiso 1 1 calc R U . . .
C12 C 0.0765(3) 0.0803(2) 0.3996(2) 0.0208(7) Uani 1 1 d . . . . .
C21 C 0.0698(3) 0.3661(3) 0.4869(2) 0.0289(8) Uani 1 1 d . . . . .
H22A H -0.0037 0.3390 0.5101 0.035 Uiso 1 1 calc R U . . .
H22B H 0.0679 0.4174 0.5240 0.035 Uiso 1 1 calc R U . . .
C20 C 0.1430(3) 0.2854(3) 0.5089(2) 0.0278(8) Uani 1 1 d . . . . .
H21A H 0.2116 0.3141 0.5011 0.033 Uiso 1 1 calc R U . . .
H21B H 0.1087 0.2492 0.5779 0.033 Uiso 1 1 calc R U . . .
N3 N 0.3313(2) 0.4071(2) 0.2524(2) 0.0219(6) Uani 1 1 d . . . . .
H3 H 0.3897 0.3669 0.2637 0.026 Uiso 1 1 calc R U . . .
C22 C 0.1799(3) 0.5003(3) 0.3451(3) 0.0305(9) Uani 1 1 d . . . . .
H23A H 0.1540 0.5394 0.3975 0.037 Uiso 1 1 calc R U . . .
H23B H 0.1769 0.5402 0.2834 0.037 Uiso 1 1 calc R U . . .
C23 C 0.2963(3) 0.4726(3) 0.3275(3) 0.0284(8) Uani 1 1 d . . . . .
H24A H 0.3432 0.5315 0.3022 0.034 Uiso 1 1 calc R U . . .
H24B H 0.3013 0.4386 0.3906 0.034 Uiso 1 1 calc R U . . .
C33 C 0.6385(3) 0.2172(3) -0.0430(3) 0.0318(9) Uani 1 1 d . . . . .
H28 H 0.6944 0.1747 -0.0675 0.038 Uiso 1 1 calc R U . . .
C34 C 0.5603(3) 0.2352(3) -0.0837(3) 0.0285(8) Uani 1 1 d . . . . .
H29 H 0.5626 0.2033 -0.1348 0.034 Uiso 1 1 calc R U . . .
C29 C 0.4763(3) 0.3014(2) -0.0491(2) 0.0221(7) Uani 1 1 d . . . . .
C27 C 0.3237(3) 0.3973(2) -0.0660(2) 0.0232(8) Uani 1 1 d . . . . .
H32 H 0.2766 0.4162 -0.0995 0.028 Uiso 1 1 calc R U . . .
C28 C 0.3979(3) 0.3253(3) -0.0942(2) 0.0244(8) Uani 1 1 d . . . . .
C25 C 0.3886(3) 0.4184(2) 0.0643(2) 0.0236(8) Uani 1 1 d . . . . .
C32 C 0.6336(3) 0.2634(3) 0.0360(3) 0.0324(9) Uani 1 1 d . . . . .
H27 H 0.6865 0.2511 0.0636 0.039 Uiso 1 1 calc R U . . .
C31 C 0.5520(3) 0.3264(3) 0.0727(3) 0.0286(8) Uani 1 1 d . . . . .
H26 H 0.5493 0.3550 0.1260 0.034 Uiso 1 1 calc R U . . .
C41 C 0.1485(3) 0.2482(2) 0.1335(2) 0.0187(7) Uani 1 1 d . . . . .
C38 C -0.0201(3) 0.3684(3) 0.1222(3) 0.0266(8) Uani 1 1 d . . . . .
C42 C 0.2393(3) 0.1887(2) 0.1438(2) 0.0196(7) Uani 1 1 d . . . . .
C43 C 0.2876(3) 0.1179(2) 0.0870(2) 0.0238(8) Uani 1 1 d . . . . .
H45 H 0.2623 0.1049 0.0394 0.029 Uiso 1 1 calc R U . . .
C45 C 0.4130(3) 0.0873(3) 0.1727(2) 0.0257(8) Uani 1 1 d . . . . .
C39 C 0.0225(3) 0.3052(3) 0.0550(2) 0.0260(8) Uani 1 1 d . . . . .
H39 H -0.0052 0.3038 0.0056 0.031 Uiso 1 1 calc R U . . .
C48 C -0.1140(3) 0.4339(3) 0.1213(3) 0.0361(10) Uani 1 1 d . . . . .
H40A H -0.1813 0.4001 0.1670 0.054 Uiso 1 1 calc R U . . .
H40B H -0.1139 0.4495 0.0541 0.054 Uiso 1 1 calc R U . . .
H40C H -0.1066 0.4938 0.1422 0.054 Uiso 1 1 calc R U . . .
C40 C 0.1057(3) 0.2443(3) 0.0612(2) 0.0231(8) Uani 1 1 d . . . . .
H38 H 0.1331 0.2008 0.0171 0.028 Uiso 1 1 calc R U . . .
C37 C 0.0270(3) 0.3692(2) 0.1922(2) 0.0241(8) Uani 1 1 d . . . . .
H36 H -0.0004 0.4114 0.2377 0.029 Uiso 1 1 calc R U . . .
C47 C 0.5069(3) 0.0350(3) 0.1906(3) 0.0350(9) Uani 1 1 d . . . . .
H43A H 0.5183 0.0570 0.2443 0.053 Uiso 1 1 calc R U . . .
H43B H 0.5713 0.0494 0.1298 0.053 Uiso 1 1 calc R U . . .
H43C H 0.4914 -0.0349 0.2090 0.053 Uiso 1 1 calc R U . . .
C44 C 0.3741(3) 0.0667(3) 0.1019(3) 0.0261(8) Uani 1 1 d . . . . .
H44 H 0.4064 0.0184 0.0647 0.031 Uiso 1 1 calc R U . . .
O10 O 1.0733(2) 0.2990(2) 0.8125(2) 0.0494(8) Uani 1 1 d . . . . .
O7 O 0.4530(2) 0.7668(2) 0.5290(2) 0.0481(8) Uani 1 1 d . . . . .
C50 C 0.2204(4) 0.6127(3) 0.5725(3) 0.0472(11) Uani 1 1 d . . . . .
N6 N 0.1496(3) 0.6596(3) 0.5686(3) 0.0700(13) Uani 1 1 d . . . . .
C49 C 0.3093(4) 0.5509(4) 0.5800(4) 0.0732(16) Uani 1 1 d . . . . .
H70A H 0.3297 0.5653 0.6323 0.110 Uiso 1 1 calc R U . . .
H70B H 0.3705 0.5638 0.5165 0.110 Uiso 1 1 calc R U . . .
H70C H 0.2865 0.4826 0.5961 0.110 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 N5 1.997(3) . ?
Cu1 N2 2.044(3) . ?
Cu1 N4 2.073(3) . ?
Cu1 N1 2.111(3) . ?
Cu1 N3 2.179(3) . ?
Cl1 O7 1.427(3) . ?
Cl1 O8 1.431(3) . ?
Cl1 O5 1.444(3) . ?
Cl1 O6 1.446(3) . ?
N5 C46 1.343(4) . ?
N5 C42 1.362(4) . ?
O3 C9 1.371(4) . ?
O3 C8 1.433(4) . ?
O4 C3 1.383(4) . ?
O4 C7 1.434(4) . ?
O2 C28 1.372(4) . ?
O2 C35 1.441(4) . ?
C13 C18 1.414(5) . ?
C13 C14 1.421(4) . ?
C13 C12 1.433(4) . ?
N1 C20 1.482(4) . ?
N1 C19 1.500(4) . ?
C46 C45 1.391(5) . ?
C30 C31 1.417(5) . ?
C30 C29 1.428(5) . ?
C30 C25 1.435(5) . ?
C11 C12 1.372(4) . ?
C11 C10 1.408(4) . ?
O1 C2 1.366(4) . ?
O1 C36 1.439(4) . ?
N4 C37 1.340(4) . ?
N4 C41 1.361(4) . ?
C24 N3 1.500(4) . ?
C24 C25 1.502(5) . ?
C19 C12 1.510(5) . ?
C10 C9 1.368(4) . ?
N2 C22 1.490(4) . ?
N2 C21 1.497(4) . ?
C26 C25 1.373(5) . ?
C26 C27 1.409(5) . ?
Cl2 O10 1.435(3) . ?
Cl2 O11 1.438(3) . ?
Cl2 O12 1.443(3) . ?
Cl2 O9 1.448(3) . ?
C2 C1 1.388(5) . ?
C2 C3 1.402(5) . ?
C4 C3 1.391(5) . ?
C4 C5 1.404(5) . ?
C1 C6 1.390(5) . ?
C6 C5 1.366(6) . ?
C7 C8 1.498(5) . ?
C36 C35 1.496(5) . ?
C16 C15 1.376(5) . ?
C16 C17 1.401(5) . ?
C14 C15 1.416(4) . ?
C14 C9 1.430(4) . ?
C17 C18 1.372(5) . ?
C21 C20 1.512(5) . ?
N3 C23 1.486(4) . ?
C22 C23 1.514(5) . ?
C33 C34 1.374(5) . ?
C33 C32 1.406(5) . ?
C34 C29 1.413(5) . ?
C29 C28 1.427(5) . ?
C27 C28 1.376(5) . ?
C32 C31 1.370(5) . ?
C41 C40 1.388(4) . ?
C41 C42 1.468(4) . ?
C38 C39 1.386(5) . ?
C38 C37 1.389(5) . ?
C38 C48 1.511(5) . ?
C42 C43 1.384(4) . ?
C43 C44 1.389(5) . ?
C45 C44 1.400(5) . ?
C45 C47 1.497(5) . ?
C39 C40 1.378(5) . ?
C50 N6 1.131(5) . ?
C50 C49 1.451(6) . ?

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
N5 Cu1 N2 179.09(11) . . ?
N5 Cu1 N4 80.49(11) . . ?
N2 Cu1 N4 100.41(11) . . ?
N5 Cu1 N1 95.45(10) . . ?
N2 Cu1 N1 84.08(11) . . ?
N4 Cu1 N1 130.05(11) . . ?
N5 Cu1 N3 95.55(10) . . ?
N2 Cu1 N3 83.88(11) . . ?
N4 Cu1 N3 120.66(10) . . ?
N1 Cu1 N3 109.29(10) . . ?
O7 Cl1 O8 110.36(19) . . ?
O7 Cl1 O5 109.73(17) . . ?
O8 Cl1 O5 109.0(2) . . ?
O7 Cl1 O6 109.41(19) . . ?
O8 Cl1 O6 109.0(2) . . ?
O5 Cl1 O6 109.33(18) . . ?
C46 N5 C42 118.9(3) . . ?
C46 N5 Cu1 125.2(2) . . ?
C42 N5 Cu1 115.9(2) . . ?
C9 O3 C8 117.3(2) . . ?
C3 O4 C7 117.0(3) . . ?
C28 O2 C35 117.5(3) . . ?
C18 C13 C14 117.2(3) . . ?
C18 C13 C12 124.0(3) . . ?
C14 C13 C12 118.7(3) . . ?
C20 N1 C19 110.3(2) . . ?
C20 N1 Cu1 106.4(2) . . ?
C19 N1 Cu1 115.39(19) . . ?
N5 C46 C45 123.6(3) . . ?
C31 C30 C29 118.0(3) . . ?
C31 C30 C25 122.2(3) . . ?
C29 C30 C25 119.8(3) . . ?
C12 C11 C10 121.9(3) . . ?
C2 O1 C36 115.8(3) . . ?
C37 N4 C41 118.8(3) . . ?
C37 N4 Cu1 128.2(2) . . ?
C41 N4 Cu1 113.0(2) . . ?
N3 C24 C25 114.5(3) . . ?
N1 C19 C12 113.6(3) . . ?
C9 C10 C11 119.6(3) . . ?
C22 N2 C21 113.8(3) . . ?
C22 N2 Cu1 108.4(2) . . ?
C21 N2 Cu1 109.8(2) . . ?
C25 C26 C27 122.6(3) . . ?
O10 Cl2 O11 109.79(17) . . ?
O10 Cl2 O12 109.05(17) . . ?
O11 Cl2 O12 110.18(17) . . ?
O10 Cl2 O9 109.58(17) . . ?
O11 Cl2 O9 109.26(16) . . ?
O12 Cl2 O9 108.96(16) . . ?
O1 C2 C1 124.5(3) . . ?
O1 C2 C3 116.5(3) . . ?
C1 C2 C3 118.9(3) . . ?
C3 C4 C5 119.7(4) . . ?
O4 C3 C4 123.6(3) . . ?
O4 C3 C2 116.3(3) . . ?
C4 C3 C2 120.2(3) . . ?
C2 C1 C6 120.7(4) . . ?
C5 C6 C1 120.4(4) . . ?
C6 C5 C4 120.1(4) . . ?
O4 C7 C8 107.8(3) . . ?
O1 C36 C35 107.8(3) . . ?
O3 C8 C7 107.6(3) . . ?
O2 C35 C36 107.7(3) . . ?
C15 C16 C17 119.9(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 C9 120.7(3) . . ?
C13 C14 C9 119.2(3) . . ?
C18 C17 C16 120.3(3) . . ?
C10 C9 O3 125.1(3) . . ?
C10 C9 C14 120.6(3) . . ?
O3 C9 C14 114.3(3) . . ?
C16 C15 C14 120.5(3) . . ?
C17 C18 C13 122.0(3) . . ?
C11 C12 C13 119.5(3) . . ?
C11 C12 C19 119.5(3) . . ?
C13 C12 C19 121.0(3) . . ?
N2 C21 C20 111.6(3) . . ?
N1 C20 C21 108.8(3) . . ?
C23 N3 C24 108.6(3) . . ?
C23 N3 Cu1 105.1(2) . . ?
C24 N3 Cu1 120.4(2) . . ?
N2 C22 C23 110.7(3) . . ?
N3 C23 C22 108.3(3) . . ?
C34 C33 C32 119.6(3) . . ?
C33 C34 C29 121.0(3) . . ?
C34 C29 C28 121.8(3) . . ?
C34 C29 C30 119.4(3) . . ?
C28 C29 C30 118.7(3) . . ?
C28 C27 C26 119.5(3) . . ?
O2 C28 C27 124.3(3) . . ?
O2 C28 C29 115.0(3) . . ?
C27 C28 C29 120.7(3) . . ?
C26 C25 C30 118.5(3) . . ?
C26 C25 C24 119.1(3) . . ?
C30 C25 C24 122.3(3) . . ?
C31 C32 C33 120.8(3) . . ?
C32 C31 C30 121.1(3) . . ?
N4 C41 C40 120.6(3) . . ?
N4 C41 C42 115.6(3) . . ?
C40 C41 C42 123.8(3) . . ?
C39 C38 C37 117.2(3) . . ?
C39 C38 C48 122.3(3) . . ?
C37 C38 C48 120.5(3) . . ?
N5 C42 C43 121.1(3) . . ?
N5 C42 C41 114.9(3) . . ?
C43 C42 C41 123.9(3) . . ?
C42 C43 C44 119.3(3) . . ?
C46 C45 C44 116.7(3) . . ?
C46 C45 C47 121.0(3) . . ?
C44 C45 C47 122.3(3) . . ?
C40 C39 C38 120.1(3) . . ?
C39 C40 C41 119.8(3) . . ?
N4 C37 C38 123.5(3) . . ?
C43 C44 C45 120.3(3) . . ?
N6 C50 C49 178.5(6) . . ?

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.075

_shelxl_version_number           2014/6

