#------------------------------------------------------------------------------
#$Date: 2021-08-25 02:03:00 +0300 (Wed, 25 Aug 2021) $
#$Revision: 268191 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/81/7708124.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7708124
loop_
_publ_author_name
'Massoud, Salah S.'
'Louka, Febee R.'
'Dial, Madison T.'
'Malek, Andrew J.'
'Fischer, Roland C.'
'Mautner, Franz A.'
'Vančo, Ján'
'Malina, Tomáš'
'Dvořák, Zdeněk'
'Trávníček, Zdeněk'
_publ_section_title
;
 Identification of potent anticancer copper(II) complexes containing
 tripodal bis[2-ethyl-di(3,5-dialkyl-1H-pyrazol-1-yl)]amine moiety.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11521
_journal_page_last               11534
_journal_paper_doi               10.1039/d1dt01724a
_journal_volume                  50
_journal_year                    2021
_chemical_formula_sum            'C43 H64 Cl4 Cu2 N12 O9'
_chemical_formula_weight         1161.96
_chemical_name_common            '[Cu(L1)Cl](ClO4)(MeOH)0.5'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-04-11 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                115.690(2)
_cell_angle_beta                 108.072(2)
_cell_angle_gamma                100.254(2)
_cell_formula_units_Z            1
_cell_length_a                   10.9839(4)
_cell_length_b                   12.3595(5)
_cell_length_c                   12.5141(5)
_cell_measurement_reflns_used    8794
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.50
_cell_volume                     1355.13(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26771
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.999
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.095
_exptl_absorpt_coefficient_mu    1.043
_exptl_absorpt_correction_T_max  0.9235
_exptl_absorpt_correction_T_min  0.7638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       prism
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         5889
_refine_ls_number_restraints     269
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0546P)²+1.6931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4554
_reflns_number_total             5889
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01724a2.cif
_cod_data_source_block           rf1186t
_cod_database_code               7708124
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.826
_shelx_estimated_absorpt_t_max   0.885
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.32706(4) 0.37868(4) 0.57688(4) 0.02286(15) Uani 1 1 d . . . . .
O1 O 0.6134(4) 0.1194(4) 0.7819(4) 0.0712(11) Uani 1 1 d . . . . .
N1 N 0.4179(4) 0.2408(4) 0.5196(4) 0.0406(9) Uani 1 1 d . . . . .
Cl1 Cl 0.30885(9) 0.56692(8) 0.59845(9) 0.0305(2) Uani 1 1 d . . . . .
Cl2 Cl 0.75946(11) 0.18771(10) 0.84172(9) 0.0373(3) Uani 1 1 d . . . . .
O2 O 0.8324(4) 0.1024(3) 0.8392(3) 0.0544(9) Uani 1 1 d . . . . .
O4 O 0.8032(5) 0.2895(4) 0.9737(4) 0.0823(13) Uani 1 1 d . . . . .
O3 O 0.7868(5) 0.2417(5) 0.7672(5) 0.0811(13) Uani 1 1 d . . . . .
N6 N 0.1918(3) 0.2790(3) 0.6334(3) 0.0304(7) Uani 1 1 d . . . . .
N5 N 0.2014(3) 0.1685(3) 0.6299(3) 0.0333(8) Uani 1 1 d . . . . .
C17 C 0.1108(4) 0.1221(4) 0.6675(4) 0.0384(10) Uani 1 1 d . U . . .
C18 C 0.0420(5) 0.2020(4) 0.6950(4) 0.0414(10) Uani 1 1 d . U . . .
H18 H -0.028418 0.193943 0.723106 0.050 Uiso 1 1 calc R U . . .
C19 C 0.0939(4) 0.2993(4) 0.6744(4) 0.0339(9) Uani 1 1 d . U . . .
C20 C 0.1017(5) 0.0032(4) 0.6760(4) 0.0563(14) Uani 1 1 d . U . . .
H20A H 0.077991 -0.070589 0.589231 0.085 Uiso 1 1 calc R U . . .
H20B H 0.030560 -0.013846 0.704432 0.085 Uiso 1 1 calc R U . . .
H20C H 0.190516 0.016846 0.739842 0.085 Uiso 1 1 calc R U . . .
C21 C 0.0549(5) 0.4150(4) 0.6978(5) 0.0459(11) Uani 1 1 d . U . . .
H21A H 0.112546 0.470056 0.681037 0.069 Uiso 1 1 calc R U . . .
H21B H 0.068640 0.463655 0.789351 0.069 Uiso 1 1 calc R U . . .
H21C H -0.041979 0.386949 0.638240 0.069 Uiso 1 1 calc R U . . .
C15A C 0.3212(6) 0.1107(6) 0.4904(6) 0.0303(17) Uani 0.654(11) 1 d . U P A 1
H15A H 0.229517 0.082833 0.419254 0.036 Uiso 0.654(11) 1 calc R U P A 1
H15B H 0.359941 0.043047 0.458933 0.036 Uiso 0.654(11) 1 calc R U P A 1
C14A C 0.390(2) 0.595(2) 0.8983(19) 0.042(4) Uani 0.596(6) 1 d . U P A 1
H14A H 0.351836 0.623542 0.837402 0.062 Uiso 0.596(6) 1 calc R U P A 1
H14B H 0.425117 0.666943 0.989277 0.062 Uiso 0.596(6) 1 calc R U P A 1
H14C H 0.317423 0.523024 0.881948 0.062 Uiso 0.596(6) 1 calc R U P A 1
C13A C 0.8617(6) 0.5750(6) 0.9455(6) 0.0328(16) Uani 0.596(6) 1 d . U P A 1
H13A H 0.871756 0.493591 0.932799 0.049 Uiso 0.596(6) 1 calc R U P A 1
H13B H 0.912252 0.642033 1.039226 0.049 Uiso 0.596(6) 1 calc R U P A 1
H13C H 0.898750 0.600606 0.894644 0.049 Uiso 0.596(6) 1 calc R U P A 1
C12A C 0.5004(14) 0.5548(14) 0.8779(12) 0.027(3) Uani 0.596(6) 1 d . U P A 1
C11A C 0.6415(14) 0.6099(11) 0.9735(11) 0.030(2) Uani 0.596(6) 1 d . U P A 1
H11A H 0.678804 0.668445 1.065842 0.036 Uiso 0.596(6) 1 calc R U P A 1
C10A C 0.7120(7) 0.5575(7) 0.8992(8) 0.0273(15) Uani 0.596(6) 1 d . U P A 1
C8A C 0.5544(6) 0.2629(7) 0.5920(6) 0.0298(16) Uani 0.596(6) 1 d . U P A 1
H8AA H 0.589023 0.208842 0.532472 0.036 Uiso 0.596(6) 1 calc R U P A 1
H8AB H 0.560578 0.238707 0.658715 0.036 Uiso 0.596(6) 1 calc R U P A 1
C7A C -0.012(2) 0.325(2) 0.378(2) 0.030(3) Uani 0.596(6) 1 d . U P A 1
H7A1 H -0.018221 0.286148 0.430543 0.045 Uiso 0.596(6) 1 calc R U P A 1
H7A2 H -0.104017 0.302864 0.313194 0.045 Uiso 0.596(6) 1 calc R U P A 1
H7A3 H 0.032314 0.419022 0.436167 0.045 Uiso 0.596(6) 1 calc R U P A 1
C6A C 0.0746(15) 0.2738(17) 0.3062(12) 0.020(3) Uani 0.596(6) 1 d . U P A 1
C5A C 0.0211(17) 0.2247(15) 0.1707(14) 0.037(4) Uani 0.596(6) 1 d . U P A 1
H5A H -0.062451 0.230900 0.126267 0.044 Uiso 0.596(6) 1 calc R U P A 1
C4A C 0.0894(9) 0.1682(8) 0.1036(9) 0.041(2) Uani 0.596(6) 1 d . U P A 1
H4A H 0.053533 0.133485 0.011207 0.050 Uiso 0.596(6) 1 calc R U P A 1
N4A N 0.5043(18) 0.4871(17) 0.7645(18) 0.032(4) Uani 0.596(6) 1 d . . P A 1
C3A C 0.2119(8) 0.1610(7) 0.1696(6) 0.0338(17) Uani 0.596(6) 1 d . U P A 1
H3A H 0.259541 0.119437 0.123111 0.041 Uiso 0.596(6) 1 calc R U P A 1
N3A N 0.6174(10) 0.4808(9) 0.7728(9) 0.020(2) Uani 0.596(6) 1 d . . P A 1
C2A C 0.2631(13) 0.2150(14) 0.3036(15) 0.025(3) Uani 0.596(6) 1 d . U P A 1
N2A N 0.198(2) 0.273(2) 0.372(2) 0.023(4) Uani 0.596(6) 1 d . U P A 1
C1A C 0.3947(8) 0.2128(7) 0.3806(7) 0.0239(17) Uani 0.596(6) 1 d . U P A 1
H1AA H 0.471196 0.277187 0.389367 0.029 Uiso 0.596(6) 1 calc R U P A 1
H1AB H 0.398726 0.126833 0.330266 0.029 Uiso 0.596(6) 1 calc R U P A 1
C16A C 0.3052(8) 0.1240(7) 0.6107(8) 0.0341(18) Uani 0.654(11) 1 d . U P A 1
H16A H 0.286022 0.038968 0.603037 0.041 Uiso 0.654(11) 1 calc R U P A 1
H16B H 0.393459 0.184102 0.689578 0.041 Uiso 0.654(11) 1 calc R U P A 1
C9A C 0.6411(8) 0.4029(7) 0.6593(7) 0.0284(16) Uani 0.596(6) 1 d . U P A 1
H9AA H 0.739524 0.413795 0.688978 0.034 Uiso 0.596(6) 1 calc R U P A 1
H9AB H 0.617708 0.432516 0.596237 0.034 Uiso 0.596(6) 1 calc R U P A 1
C19B C 0.4265(11) 0.1786(11) 0.5972(11) 0.033(3) Uani 0.346(11) 1 d . U P A 2
H19A H 0.466040 0.243292 0.692622 0.039 Uiso 0.346(11) 1 calc R U P A 2
H19B H 0.482647 0.124124 0.582017 0.039 Uiso 0.346(11) 1 calc R U P A 2
C13B C 0.1540(11) 0.1224(10) 0.0390(10) 0.037(3) Uani 0.404(6) 1 d . U P A 2
H13D H 0.068402 0.097949 -0.035839 0.056 Uiso 0.404(6) 1 calc R U P A 2
H13E H 0.174761 0.045208 0.027417 0.056 Uiso 0.404(6) 1 calc R U P A 2
H13F H 0.229364 0.183027 0.043765 0.056 Uiso 0.404(6) 1 calc R U P A 2
C10B C 0.1382(12) 0.1843(10) 0.1627(11) 0.026(2) Uani 0.404(6) 1 d D U P A 2
N3B N 0.194(4) 0.286(4) 0.386(4) 0.024(6) Uani 0.404(6) 1 d . U P A 2
N4B N 0.2357(16) 0.2330(16) 0.2873(19) 0.033(4) Uani 0.404(6) 1 d . . P A 2
C4B C 0.7656(15) 0.6141(14) 0.9628(14) 0.050(3) Uani 0.404(6) 1 d . U P A 2
H4B H 0.854188 0.659571 1.035417 0.060 Uiso 0.404(6) 1 calc R U P A 2
C3B C 0.7441(12) 0.5187(12) 0.8431(12) 0.041(3) Uani 0.404(6) 1 d . U P A 2
H3B H 0.820303 0.499381 0.830540 0.049 Uiso 0.404(6) 1 calc R U P A 2
C1B C 0.5855(12) 0.3518(12) 0.6104(11) 0.031(2) Uani 0.404(6) 1 d . U P A 2
H1BA H 0.648965 0.304654 0.615871 0.037 Uiso 0.404(6) 1 calc R U P A 2
H1BB H 0.603083 0.393648 0.561951 0.037 Uiso 0.404(6) 1 calc R U P A 2
C6B C 0.526(2) 0.577(2) 0.881(2) 0.030(5) Uani 0.404(6) 1 d D U P A 2
C5B C 0.655(3) 0.6412(19) 0.974(2) 0.042(5) Uani 0.404(6) 1 d . U P A 2
H5B H 0.669969 0.712566 1.054865 0.051 Uiso 0.404(6) 1 calc R U P A 2
C2B C 0.618(2) 0.4507(18) 0.7418(18) 0.025(4) Uani 0.404(6) 1 d . U P A 2
C7B C 0.393(3) 0.579(3) 0.911(3) 0.042(6) Uani 0.404(6) 1 d D U P A 2
H7BA H 0.338174 0.612659 0.865270 0.063 Uiso 0.404(6) 1 calc R U P A 2
H7BB H 0.424255 0.634005 1.006610 0.063 Uiso 0.404(6) 1 calc R U P A 2
H7BC H 0.337562 0.490986 0.881325 0.063 Uiso 0.404(6) 1 calc R U P A 2
C9B C 0.3758(11) 0.2386(12) 0.3183(12) 0.046(3) Uani 0.404(6) 1 d . U P A 2
H9B1 H 0.439790 0.329451 0.370461 0.060 Uiso 0.404(6) 1 calc R U P A 2
H9B2 H 0.386253 0.193687 0.236044 0.060 Uiso 0.404(6) 1 calc R U P A 2
C98 C 0.4082(13) 0.1749(13) 0.3955(12) 0.036(3) Uani 0.404(6) 1 d . U P A 2
H98A H 0.335718 0.088303 0.346701 0.047 Uiso 0.404(6) 1 calc R U P A 2
H98B H 0.496307 0.162869 0.401784 0.047 Uiso 0.404(6) 1 calc R U P A 2
C14 C -0.008(4) 0.329(4) 0.403(3) 0.042(8) Uani 0.404(6) 1 d . U P A 2
H14D H -0.023608 0.282008 0.445995 0.062 Uiso 0.404(6) 1 calc R U P A 2
H14E H -0.095827 0.324792 0.346678 0.062 Uiso 0.404(6) 1 calc R U P A 2
H14F H 0.050364 0.419814 0.470148 0.062 Uiso 0.404(6) 1 calc R U P A 2
C12B C 0.059(2) 0.274(3) 0.3254(17) 0.024(5) Uani 0.404(6) 1 d D U P A 2
C11B C 0.024(2) 0.211(2) 0.1867(18) 0.028(5) Uani 0.404(6) 1 d D U P A 2
H11B H -0.063274 0.189929 0.120102 0.034 Uiso 0.404(6) 1 calc R U P A 2
N2B N 0.482(2) 0.468(2) 0.750(2) 0.014(4) Uani 0.404(6) 1 d . U P A 2
C18B C 0.2771(16) 0.0975(14) 0.5448(18) 0.041(4) Uani 0.346(11) 1 d . U P A 2
H18A H 0.272637 0.016253 0.543733 0.050 Uiso 0.346(11) 1 calc R U P A 2
H18B H 0.226667 0.074615 0.452763 0.050 Uiso 0.346(11) 1 calc R U P A 2
O5 O 0.6108(11) 0.0976(11) 1.0643(12) 0.053(3) Uani 0.3 1 d D U P B 1
H90 H 0.609400 0.096320 0.998528 0.080 Uiso 0.3 1 d . U P C 1
C22 C 0.6301(17) -0.0115(13) 1.0426(17) 0.048(4) Uani 0.3 1 d D U P B 1
H22A H 0.727928 0.002647 1.067694 0.072 Uiso 0.3 1 calc R U P B 1
H22B H 0.576529 -0.077694 0.948813 0.072 Uiso 0.3 1 calc R U P B 1
H22C H 0.600066 -0.039996 1.095149 0.072 Uiso 0.3 1 calc R U P B 1
O6 O 0.4735(13) 0.0848(15) 0.9873(16) 0.041(4) Uani 0.2 1 d D U P D 2
H91 H 0.380190 0.056520 0.941489 0.062 Uiso 0.2 1 d . U P E 2
C23 C 0.568(3) 0.072(4) 1.090(3) 0.086(11) Uani 0.2 1 d D U P D 2
H23A H 0.609049 0.010279 1.050169 0.128 Uiso 0.2 1 calc R U P D 2
H23B H 0.516625 0.039880 1.128396 0.128 Uiso 0.2 1 calc R U P D 2
H23C H 0.640309 0.155641 1.158299 0.128 Uiso 0.2 1 calc R U P D 2
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'
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
N2B Cu1 N3B 169.5(14) . . ?
N2B Cu1 N1 86.9(7) . . ?
N3B Cu1 N1 86.5(12) . . ?
N2A Cu1 N1 81.9(8) . . ?
N2A Cu1 N4A 163.0(9) . . ?
N1 Cu1 N4A 87.6(5) . . ?
N2B Cu1 N6 93.2(8) . . ?
N3B Cu1 N6 95.7(13) . . ?
N2A Cu1 N6 97.2(7) . . ?
N1 Cu1 N6 96.52(13) . . ?
N4A Cu1 N6 97.2(6) . . ?
N2B Cu1 Cl1 92.2(7) . . ?
N3B Cu1 Cl1 89.1(13) . . ?
N2A Cu1 Cl1 92.5(8) . . ?
N1 Cu1 Cl1 147.71(11) . . ?
N4A Cu1 Cl1 89.3(6) . . ?
N6 Cu1 Cl1 115.76(8) . . ?
C98 N1 C19B 119.6(8) . . ?
C8A N1 C1A 109.7(5) . . ?
C8A N1 C15A 109.6(4) . . ?
C1A N1 C15A 102.9(4) . . ?
C98 N1 C1B 103.1(7) . . ?
C19B N1 C1B 97.6(6) . . ?
C98 N1 Cu1 123.2(6) . . ?
C8A N1 Cu1 123.1(4) . . ?
C19B N1 Cu1 110.4(5) . . ?
C1A N1 Cu1 101.7(4) . . ?
C15A N1 Cu1 107.8(3) . . ?
C1B N1 Cu1 95.1(4) . . ?
O4 Cl2 O3 109.0(3) . . ?
O4 Cl2 O2 110.6(2) . . ?
O3 Cl2 O2 108.7(2) . . ?
O4 Cl2 O1 109.7(3) . . ?
O3 Cl2 O1 107.8(3) . . ?
O2 Cl2 O1 111.0(2) . . ?
C19 N6 N5 104.7(3) . . ?
C19 N6 Cu1 135.8(3) . . ?
N5 N6 Cu1 119.5(2) . . ?
C17 N5 N6 110.8(3) . . ?
C17 N5 C16A 125.5(4) . . ?
N6 N5 C16A 123.0(4) . . ?
C17 N5 C18B 130.6(7) . . ?
N6 N5 C18B 115.5(7) . . ?
C18 C17 N5 107.5(4) . . ?
C18 C17 C20 130.3(4) . . ?
N5 C17 C20 122.2(4) . . ?
C17 C18 C19 106.7(4) . . ?
C17 C18 H18 126.7 . . ?
C19 C18 H18 126.7 . . ?
N6 C19 C18 110.4(4) . . ?
N6 C19 C21 122.3(4) . . ?
C18 C19 C21 127.3(4) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16A C15A N1 112.3(5) . . ?
C16A C15A H15A 109.2 . . ?
N1 C15A H15A 109.2 . . ?
C16A C15A H15B 109.2 . . ?
N1 C15A H15B 109.2 . . ?
H15A C15A H15B 107.9 . . ?
C12A C14A H14A 109.5 . . ?
C12A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C12A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C10A C13A H13A 109.5 . . ?
C10A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C10A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
N4A C12A C14A 127.3(15) . . ?
N4A C12A C11A 104.0(14) . . ?
C14A C12A C11A 126.4(14) . . ?
C10A C11A C12A 104.3(10) . . ?
C10A C11A H11A 127.8 . . ?
C12A C11A H11A 127.8 . . ?
N3A C10A C11A 106.7(8) . . ?
N3A C10A C13A 124.0(8) . . ?
C11A C10A C13A 129.2(8) . . ?
N1 C8A C9A 110.0(6) . . ?
N1 C8A H8AA 109.7 . . ?
C9A C8A H8AA 109.7 . . ?
N1 C8A H8AB 109.7 . . ?
C9A C8A H8AB 109.7 . . ?
H8AA C8A H8AB 108.2 . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
N2A C6A C5A 121.0(18) . . ?
N2A C6A C7A 120.6(17) . . ?
C5A C6A C7A 118.4(16) . . ?
C4A C5A C6A 119.2(15) . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A H5A 120.4 . . ?
C5A C4A C3A 119.9(10) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
N3A N4A C12A 115.2(15) . . ?
N3A N4A Cu1 120.4(13) . . ?
C12A N4A Cu1 124.2(13) . . ?
C4A C3A C2A 118.7(9) . . ?
C4A C3A H3A 120.6 . . ?
C2A C3A H3A 120.6 . . ?
N4A N3A C10A 109.5(11) . . ?
N4A N3A C9A 123.7(11) . . ?
C10A N3A C9A 126.8(9) . . ?
N2A C2A C3A 122.4(13) . . ?
N2A C2A C1A 116.1(15) . . ?
C3A C2A C1A 121.5(12) . . ?
C2A N2A C6A 118.6(19) . . ?
C2A N2A Cu1 111.1(14) . . ?
C6A N2A Cu1 129.4(19) . . ?
C2A C1A N1 115.0(9) . . ?
C2A C1A H1AA 108.5 . . ?
N1 C1A H1AA 108.5 . . ?
C2A C1A H1AB 108.5 . . ?
N1 C1A H1AB 108.5 . . ?
H1AA C1A H1AB 107.5 . . ?
N5 C16A C15A 114.5(6) . . ?
N5 C16A H16A 108.6 . . ?
C15A C16A H16A 108.6 . . ?
N5 C16A H16B 108.6 . . ?
C15A C16A H16B 108.6 . . ?
H16A C16A H16B 107.6 . . ?
N3A C9A C8A 110.2(7) . . ?
N3A C9A H9AA 109.6 . . ?
C8A C9A H9AA 109.6 . . ?
N3A C9A H9AB 109.6 . . ?
C8A C9A H9AB 109.6 . . ?
H9AA C9A H9AB 108.1 . . ?
N1 C19B C18B 102.7(9) . . ?
N1 C19B H19A 111.2 . . ?
C18B C19B H19A 111.2 . . ?
N1 C19B H19B 111.2 . . ?
C18B C19B H19B 111.2 . . ?
H19A C19B H19B 109.1 . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
N4B C10B C11B 101.8(13) . . ?
N4B C10B C13B 126.7(13) . . ?
C11B C10B C13B 131.5(12) . . ?
C12B N3B N4B 107(3) . . ?
C12B N3B Cu1 131(3) . . ?
N4B N3B Cu1 121(2) . . ?
C10B N4B N3B 115(2) . . ?
C10B N4B C9B 123.7(18) . . ?
N3B N4B C9B 121(2) . . ?
C5B C4B C3B 116.7(15) . . ?
C5B C4B H4B 121.7 . . ?
C3B C4B H4B 121.7 . . ?
C2B C3B C4B 121.8(15) . . ?
C2B C3B H3B 119.1 . . ?
C4B C3B H3B 119.1 . . ?
C2B C1B N1 115.3(11) . . ?
C2B C1B H1BA 108.4 . . ?
N1 C1B H1BA 108.4 . . ?
C2B C1B H1BB 108.4 . . ?
N1 C1B H1BB 108.4 . . ?
H1BA C1B H1BB 107.5 . . ?
C5B C6B N2B 126(2) . . ?
C5B C6B C7B 123(2) . . ?
N2B C6B C7B 108.3(19) . . ?
C6B C5B C4B 126(2) . . ?
C6B C5B H5B 117.2 . . ?
C4B C5B H5B 117.2 . . ?
C3B C2B C1B 125.9(17) . . ?
C3B C2B N2B 124.6(16) . . ?
C1B C2B N2B 109.5(15) . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
N4B C9B C98 108.3(13) . . ?
N4B C9B H9B1 110.0 . . ?
C98 C9B H9B1 110.0 . . ?
N4B C9B H9B2 110.0 . . ?
C98 C9B H9B2 110.0 . . ?
H9B1 C9B H9B2 108.4 . . ?
N1 C98 C9B 114.6(10) . . ?
N1 C98 H98A 108.6 . . ?
C9B C98 H98A 108.6 . . ?
N1 C98 H98B 108.6 . . ?
C9B C98 H98B 108.6 . . ?
H98A C98 H98B 107.6 . . ?
C12B C14 H14D 109.5 . . ?
C12B C14 H14E 109.5 . . ?
H14D C14 H14E 109.5 . . ?
C12B C14 H14F 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
N3B C12B C14 120(3) . . ?
N3B C12B C11B 105(2) . . ?
C14 C12B C11B 135(3) . . ?
C12B C11B C10B 110.7(18) . . ?
C12B C11B H11B 124.6 . . ?
C10B C11B H11B 124.6 . . ?
C6B N2B C2B 105.1(16) . . ?
C6B N2B Cu1 139.3(17) . . ?
C2B N2B Cu1 112.0(15) . . ?
C19B C18B N5 113.6(11) . . ?
C19B C18B H18A 108.9 . . ?
N5 C18B H18A 108.9 . . ?
C19B C18B H18B 108.9 . . ?
N5 C18B H18B 108.9 . . ?
H18A C18B H18B 107.7 . . ?
C22 O5 H90 100.3(13) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O6 H91 136(2) . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 N2B 1.94(2) . ?
Cu1 N3B 2.00(4) . ?
Cu1 N2A 2.11(2) . ?
Cu1 N1 2.098(3) . ?
Cu1 N4A 2.146(17) . ?
Cu1 N6 2.231(3) . ?
Cu1 Cl1 2.2762(10) . ?
O1 Cl2 1.439(4) . ?
N1 C98 1.363(13) . ?
N1 C8A 1.393(7) . ?
N1 C19B 1.470(12) . ?
N1 C1A 1.544(8) . ?
N1 C15A 1.578(7) . ?
N1 C1B 1.736(13) . ?
Cl2 O4 1.426(4) . ?
Cl2 O3 1.431(4) . ?
Cl2 O2 1.429(3) . ?
N6 C19 1.346(5) . ?
N6 N5 1.372(4) . ?
N5 C17 1.364(5) . ?
N5 C16A 1.392(8) . ?
N5 C18B 1.611(17) . ?
C17 C18 1.340(7) . ?
C17 C20 1.507(6) . ?
C18 C19 1.398(6) . ?
C18 H18 0.9500 . ?
C19 C21 1.499(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C15A C16A 1.512(10) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C14A C12A 1.45(2) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C13A C10A 1.504(10) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C12A N4A 1.32(2) . ?
C12A C11A 1.436(18) . ?
C11A C10A 1.410(18) . ?
C11A H11A 0.9500 . ?
C10A N3A 1.345(12) . ?
C8A C9A 1.504(10) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C7A C6A 1.53(3) . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C6A N2A 1.36(3) . ?
C6A C5A 1.397(17) . ?
C5A C4A 1.352(17) . ?
C5A H5A 0.9500 . ?
C4A C3A 1.384(11) . ?
C4A H4A 0.9500 . ?
N4A N3A 1.23(2) . ?
C3A C2A 1.372(17) . ?
C3A H3A 0.9500 . ?
N3A C9A 1.465(10) . ?
C2A N2A 1.34(3) . ?
C2A C1A 1.481(13) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C19B C18B 1.518(19) . ?
C19B H19A 0.9900 . ?
C19B H19B 0.9900 . ?
C13B C10B 1.483(15) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C10B N4B 1.36(2) . ?
C10B C11B 1.442(18) . ?
N3B C12B 1.39(5) . ?
N3B N4B 1.39(5) . ?
N4B C9B 1.447(18) . ?
C4B C5B 1.35(3) . ?
C4B C3B 1.357(18) . ?
C4B H4B 0.9500 . ?
C3B C2B 1.34(2) . ?
C3B H3B 0.9500 . ?
C1B C2B 1.437(19) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C6B C5B 1.33(3) . ?
C6B N2B 1.44(3) . ?
C6B C7B 1.62(3) . ?
C5B H5B 0.9500 . ?
C2B N2B 1.58(3) . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
C9B C98 1.492(18) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C98 H98A 0.9900 . ?
C98 H98B 0.9900 . ?
C14 C12B 1.41(5) . ?
C14 H14D 0.9800 . ?
C14 H14E 0.9800 . ?
C14 H14F 0.9800 . ?
C12B C11B 1.440(17) . ?
C11B H11B 0.9500 . ?
C18B H18A 0.9900 . ?
C18B H18B 0.9900 . ?
O5 C22 1.325(9) . ?
O5 H90 0.812(12) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O6 C23 1.468(10) . ?
O6 H91 0.914(12) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
C19 N6 N5 C17 0.3(4) . . . . ?
Cu1 N6 N5 C17 -179.9(2) . . . . ?
C19 N6 N5 C16A -170.4(5) . . . . ?
Cu1 N6 N5 C16A 9.4(6) . . . . ?
C19 N6 N5 C18B 162.6(7) . . . . ?
Cu1 N6 N5 C18B -17.5(7) . . . . ?
N6 N5 C17 C18 0.2(4) . . . . ?
C16A N5 C17 C18 170.6(5) . . . . ?
C18B N5 C17 C18 -158.7(9) . . . . ?
N6 N5 C17 C20 -178.5(3) . . . . ?
C16A N5 C17 C20 -8.1(7) . . . . ?
C18B N5 C17 C20 22.6(10) . . . . ?
N5 C17 C18 C19 -0.5(4) . . . . ?
C20 C17 C18 C19 178.0(4) . . . . ?
N5 N6 C19 C18 -0.6(4) . . . . ?
Cu1 N6 C19 C18 179.6(3) . . . . ?
N5 N6 C19 C21 177.2(4) . . . . ?
Cu1 N6 C19 C21 -2.6(6) . . . . ?
C17 C18 C19 N6 0.7(5) . . . . ?
C17 C18 C19 C21 -177.0(4) . . . . ?
C8A N1 C15A C16A 74.8(6) . . . . ?
C1A N1 C15A C16A -168.6(5) . . . . ?
Cu1 N1 C15A C16A -61.6(5) . . . . ?
N4A C12A C11A C10A -3.6(16) . . . . ?
C14A C12A C11A C10A -167.4(16) . . . . ?
C12A C11A C10A N3A 0.6(12) . . . . ?
C12A C11A C10A C13A -177.1(9) . . . . ?
C1A N1 C8A C9A 87.0(6) . . . . ?
C15A N1 C8A C9A -160.8(5) . . . . ?
Cu1 N1 C8A C9A -32.4(7) . . . . ?
N2A C6A C5A C4A 4(3) . . . . ?
C7A C6A C5A C4A -173.9(15) . . . . ?
C6A C5A C4A C3A -0.8(19) . . . . ?
C14A C12A N4A N3A 169.6(18) . . . . ?
C11A C12A N4A N3A 6(2) . . . . ?
C14A C12A N4A Cu1 -16(3) . . . . ?
C11A C12A N4A Cu1 -179.6(13) . . . . ?
C5A C4A C3A C2A -1.7(15) . . . . ?
C12A N4A N3A C10A -6(2) . . . . ?
Cu1 N4A N3A C10A 179.4(10) . . . . ?
C12A N4A N3A C9A 175.5(13) . . . . ?
Cu1 N4A N3A C9A 1(2) . . . . ?
C11A C10A N3A N4A 3.0(16) . . . . ?
C13A C10A N3A N4A -179.2(13) . . . . ?
C11A C10A N3A C9A -178.4(10) . . . . ?
C13A C10A N3A C9A -0.6(15) . . . . ?
C4A C3A C2A N2A 1(2) . . . . ?
C4A C3A C2A C1A -178.9(9) . . . . ?
C3A C2A N2A C6A 3(3) . . . . ?
C1A C2A N2A C6A -177.5(17) . . . . ?
C3A C2A N2A Cu1 -167.5(11) . . . . ?
C1A C2A N2A Cu1 12(2) . . . . ?
C5A C6A N2A C2A -5(3) . . . . ?
C7A C6A N2A C2A 173(2) . . . . ?
C5A C6A N2A Cu1 163.0(17) . . . . ?
C7A C6A N2A Cu1 -19(3) . . . . ?
N2A C2A C1A N1 17.2(19) . . . . ?
C3A C2A C1A N1 -163.2(10) . . . . ?
C8A N1 C1A C2A -167.6(8) . . . . ?
C15A N1 C1A C2A 75.8(8) . . . . ?
Cu1 N1 C1A C2A -35.8(8) . . . . ?
C17 N5 C16A C15A 137.9(5) . . . . ?
N6 N5 C16A C15A -52.8(8) . . . . ?
N1 C15A C16A N5 86.1(7) . . . . ?
N4A N3A C9A C8A -60.3(17) . . . . ?
C10A N3A C9A C8A 121.4(10) . . . . ?
N1 C8A C9A N3A 75.2(8) . . . . ?
C98 N1 C19B C18B -81.5(12) . . . . ?
C1B N1 C19B C18B 168.7(9) . . . . ?
Cu1 N1 C19B C18B 70.4(9) . . . . ?
C11B C10B N4B N3B 0(3) . . . . ?
C13B C10B N4B N3B 180(2) . . . . ?
C11B C10B N4B C9B -175.2(16) . . . . ?
C13B C10B N4B C9B 4(2) . . . . ?
C12B N3B N4B C10B 0(4) . . . . ?
Cu1 N3B N4B C10B -174(2) . . . . ?
C12B N3B N4B C9B 175(2) . . . . ?
Cu1 N3B N4B C9B 2(4) . . . . ?
C5B C4B C3B C2B -3(2) . . . . ?
C98 N1 C1B C2B 169.4(14) . . . . ?
C19B N1 C1B C2B -67.8(14) . . . . ?
Cu1 N1 C1B C2B 43.6(13) . . . . ?
N2B C6B C5B C4B -2(4) . . . . ?
C7B C6B C5B C4B 158(2) . . . . ?
C3B C4B C5B C6B 5(3) . . . . ?
C4B C3B C2B C1B 177.3(16) . . . . ?
C4B C3B C2B N2B -3(3) . . . . ?
N1 C1B C2B C3B 156.4(16) . . . . ?
N1 C1B C2B N2B -24(2) . . . . ?
C10B N4B C9B C98 -126.6(16) . . . . ?
N3B N4B C9B C98 58(3) . . . . ?
C19B N1 C98 C9B 169.9(9) . . . . ?
C1B N1 C98 C9B -83.3(11) . . . . ?
Cu1 N1 C98 C9B 21.8(14) . . . . ?
N4B C9B C98 N1 -69.5(15) . . . . ?
N4B N3B C12B C14 -175(3) . . . . ?
Cu1 N3B C12B C14 -3(6) . . . . ?
N4B N3B C12B C11B 0(4) . . . . ?
Cu1 N3B C12B C11B 173(3) . . . . ?
N3B C12B C11B C10B 0(3) . . . . ?
C14 C12B C11B C10B 174(3) . . . . ?
N4B C10B C11B C12B 0(2) . . . . ?
C13B C10B C11B C12B -179.6(17) . . . . ?
C5B C6B N2B C2B -3(3) . . . . ?
C7B C6B N2B C2B -165(2) . . . . ?
C5B C6B N2B Cu1 -159(2) . . . . ?
C7B C6B N2B Cu1 39(4) . . . . ?
C3B C2B N2B C6B 5(3) . . . . ?
C1B C2B N2B C6B -174.6(19) . . . . ?
C3B C2B N2B Cu1 168.3(17) . . . . ?
C1B C2B N2B Cu1 -12(2) . . . . ?
N1 C19B C18B N5 -94.0(12) . . . . ?
C17 N5 C18B C19B -139.4(9) . . . . ?
N6 N5 C18B C19B 62.5(13) . . . . ?
