#------------------------------------------------------------------------------
#$Date: 2021-08-25 02:03:00 +0300 (Wed, 25 Aug 2021) $
#$Revision: 268191 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/81/7708125.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_7708125
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_moiety         'C22 H32 Cl Cu N6 O2, Cl O4'
_chemical_formula_sum            'C22 H32 Cl2 Cu N6 O6'
_chemical_formula_weight         610.97
_chemical_name_common            '[Cu(L2)Cl]ClO4'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-11 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.876(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3521(9)
_cell_length_b                   20.4978(9)
_cell_length_c                   15.1917(7)
_cell_measurement_reflns_used    9632
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.42
_cell_volume                     6125.2(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            79236
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.999
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.435
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1516 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.8018. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       Block
_exptl_crystal_F_000             2536
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6021
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0536P)²+29.4702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4864
_reflns_number_total             6021
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01724a2.cif
_cod_data_source_block           rf1178_0m_a
_cod_database_code               7708125
_shelx_shelxl_version_number     2018/3
_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_max   0.881
_shelx_estimated_absorpt_t_min   0.794
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O6A \\sim O6B \\sim O7A \\sim O7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(O6B)=Sof(Cl2B)=Sof(O7B)=1-FVAR(1)
 Sof(O6A)=Sof(Cl2A)=Sof(O7A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B), C10(H10A,H10B), C16(H16A,H16B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C12(H12), C19(H19)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C1 C 0.6417(2) 0.65201(18) 0.8340(3) 0.0334(8) Uani 1 1 d . . . . .
H1A H 0.660887 0.633667 0.895562 0.040 Uiso 1 1 calc R . . . .
H1B H 0.603519 0.623863 0.801942 0.040 Uiso 1 1 calc R . . . .
C2 C 0.61651(18) 0.71984(17) 0.8418(2) 0.0271(7) Uani 1 1 d . . . . .
C3 C 0.55345(18) 0.73222(17) 0.8558(2) 0.0281(8) Uani 1 1 d . . . . .
C4 C 0.53358(18) 0.79681(18) 0.8644(2) 0.0309(8) Uani 1 1 d . . . . .
O4 O 0.8595(2) 0.59107(14) 0.6580(2) 0.0642(10) Uani 1 1 d . . . . .
N4 N 0.84110(16) 0.69515(16) 0.8389(2) 0.0361(7) Uani 1 1 d . . . . .
C5 C 0.57922(18) 0.84610(18) 0.8592(3) 0.0328(8) Uani 1 1 d . . . . .
H5 H 0.567439 0.890469 0.864879 0.039 Uiso 1 1 calc R . . . .
O5 O 0.8426(2) 0.48548(16) 0.7082(2) 0.0727(11) Uani 1 1 d . . . . .
N5 N 0.70860(15) 0.74765(15) 0.6156(2) 0.0314(7) Uani 1 1 d . . . . .
C6 C 0.64147(18) 0.83030(17) 0.8459(3) 0.0308(8) Uani 1 1 d . . . . .
H6 H 0.672334 0.864537 0.843113 0.037 Uiso 1 1 calc R . . . .
N6 N 0.74251(16) 0.78387(16) 0.6889(2) 0.0337(7) Uani 1 1 d . . . . .
C7 C 0.5104(2) 0.6625(2) 0.9511(3) 0.0425(10) Uani 1 1 d . . . . .
H7A H 0.480838 0.624593 0.949490 0.064 Uiso 1 1 calc GR . . . .
H7B H 0.493315 0.699215 0.980207 0.064 Uiso 1 1 calc GR . . . .
H7C H 0.556700 0.651734 0.985966 0.064 Uiso 1 1 calc GR . . . .
C8 C 0.4490(2) 0.8721(2) 0.8820(3) 0.0428(10) Uani 1 1 d . . . . .
H8A H 0.451707 0.896398 0.827481 0.064 Uiso 1 1 calc GR . . . .
H8B H 0.478906 0.892471 0.935976 0.064 Uiso 1 1 calc GR . . . .
H8C H 0.402087 0.872626 0.887489 0.064 Uiso 1 1 calc GR . . . .
C9 C 0.7350(2) 0.59182(19) 0.8003(3) 0.0366(9) Uani 1 1 d . . . . .
H9A H 0.753953 0.582154 0.747885 0.044 Uiso 1 1 calc R . . . .
H9B H 0.704420 0.555459 0.806348 0.044 Uiso 1 1 calc R . . . .
C10 C 0.7926(2) 0.5963(2) 0.8864(3) 0.0417(10) Uani 1 1 d . . . . .
H10A H 0.776208 0.618448 0.934615 0.050 Uiso 1 1 calc R . . . .
H10B H 0.807482 0.551807 0.907986 0.050 Uiso 1 1 calc R . . . .
C11 C 0.9147(2) 0.6122(2) 0.8776(2) 0.0440(11) Uani 1 1 d . . . . .
C12 C 0.9485(2) 0.6640(2) 0.8524(3) 0.0452(11) Uani 1 1 d . . . . .
H12 H 0.994934 0.664903 0.851107 0.054 Uiso 1 1 calc R . . . .
C13 C 0.90180(19) 0.7152(2) 0.8289(2) 0.0392(9) Uani 1 1 d . . . . .
C14 C 0.9375(3) 0.5440(2) 0.9051(3) 0.0625(15) Uani 1 1 d . . . . .
H14A H 0.912263 0.513334 0.859267 0.094 Uiso 1 1 calc GR . . . .
H14B H 0.928857 0.534122 0.964215 0.094 Uiso 1 1 calc GR . . . .
H14C H 0.986231 0.540061 0.909690 0.094 Uiso 1 1 calc GR . . . .
C15 C 0.9132(2) 0.7822(2) 0.7976(3) 0.0472(11) Uani 1 1 d . . . . .
H15A H 0.883202 0.789632 0.736737 0.071 Uiso 1 1 calc GR . . . .
H15B H 0.960654 0.786766 0.795392 0.071 Uiso 1 1 calc GR . . . .
H15C H 0.903124 0.814359 0.840121 0.071 Uiso 1 1 calc GR . . . .
C16 C 0.65852(19) 0.65665(19) 0.6838(2) 0.0331(8) Uani 1 1 d . . . . .
H16A H 0.620358 0.687903 0.675836 0.040 Uiso 1 1 calc R . . . .
H16B H 0.639022 0.613199 0.663899 0.040 Uiso 1 1 calc R . . . .
C17 C 0.7040(2) 0.67745(19) 0.6228(2) 0.0352(9) Uani 1 1 d . . . . .
H17A H 0.750173 0.659403 0.647722 0.042 Uiso 1 1 calc R . . . .
H17B H 0.685785 0.658874 0.561204 0.042 Uiso 1 1 calc R . . . .
C18 C 0.68708(19) 0.7856(2) 0.5395(2) 0.0352(9) Uani 1 1 d . . . . .
C19 C 0.7085(2) 0.8477(2) 0.5646(3) 0.0380(9) Uani 1 1 d . . . . .
H19 H 0.701739 0.885134 0.526477 0.046 Uiso 1 1 calc R . . . .
C20 C 0.7424(2) 0.8453(2) 0.6578(3) 0.0367(9) Uani 1 1 d . . . . .
C21 C 0.6454(2) 0.7593(2) 0.4509(3) 0.0421(10) Uani 1 1 d . . . . .
H21A H 0.638535 0.793481 0.404430 0.063 Uiso 1 1 calc GR . . . .
H21B H 0.601233 0.744726 0.458212 0.063 Uiso 1 1 calc GR . . . .
H21C H 0.669168 0.722283 0.432151 0.063 Uiso 1 1 calc GR . . . .
C22 C 0.7743(2) 0.9001(2) 0.7176(3) 0.0486(11) Uani 1 1 d . . . . .
H22A H 0.810669 0.919163 0.694387 0.073 Uiso 1 1 calc GR . . . .
H22B H 0.793287 0.883792 0.779583 0.073 Uiso 1 1 calc GR . . . .
H22C H 0.739893 0.933385 0.718324 0.073 Uiso 1 1 calc GR . . . .
N2 N 0.66061(15) 0.76875(14) 0.8367(2) 0.0282(6) Uani 1 1 d . . . . .
Cu1 Cu 0.75221(2) 0.74006(2) 0.82721(3) 0.02803(14) Uani 1 1 d . . . . .
N1 N 0.69517(16) 0.65345(15) 0.7825(2) 0.0308(7) Uani 1 1 d . . . . .
Cl1 Cl 0.80283(5) 0.81553(5) 0.93574(6) 0.0370(2) Uani 1 1 d . . . . .
O1 O 0.51101(13) 0.68030(12) 0.85957(16) 0.0323(6) Uani 1 1 d . . . . .
O2 O 0.47024(12) 0.80538(13) 0.87474(18) 0.0359(6) Uani 1 1 d . . . . .
N3 N 0.85002(17) 0.63226(16) 0.8699(2) 0.0363(8) Uani 1 1 d . . . . .
O6A O 0.7720(4) 0.5338(4) 0.5885(8) 0.103(4) Uani 0.539(8) 1 d . U P A 1
Cl2A Cl 0.8424(4) 0.5254(4) 0.6291(6) 0.0332(14) Uani 0.539(8) 1 d . . P A 1
O7A O 0.8760(5) 0.5012(3) 0.5664(5) 0.068(2) Uani 0.539(8) 1 d . U P A 1
O6B O 0.8157(7) 0.5053(4) 0.5564(5) 0.074(3) Uani 0.461(8) 1 d . U P A 2
Cl2B Cl 0.8592(5) 0.5261(5) 0.6430(7) 0.0317(15) Uani 0.461(8) 1 d . . P A 2
O7B O 0.9268(5) 0.5073(4) 0.6516(9) 0.090(4) Uani 0.461(8) 1 d . U P A 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'
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'
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'
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
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.4(3) . . ?
C3 C2 C1 122.3(3) . . ?
N2 C2 C1 115.8(3) . . ?
N2 C2 C3 121.8(3) . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 O1 118.8(3) . . ?
O1 C3 C4 121.7(3) . . ?
C5 C4 C3 118.0(3) . . ?
O2 C4 C3 116.2(3) . . ?
O2 C4 C5 125.8(3) . . ?
C13 N4 Cu1 133.3(3) . . ?
C13 N4 N3 106.4(3) . . ?
N3 N4 Cu1 120.1(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
N6 N5 C17 120.4(3) . . ?
N6 N5 C18 111.4(3) . . ?
C18 N5 C17 128.0(3) . . ?
C5 C6 H6 118.6 . . ?
N2 C6 C5 122.9(3) . . ?
N2 C6 H6 118.6 . . ?
N5 N6 Cu1 116.7(2) . . ?
C20 N6 N5 105.5(3) . . ?
C20 N6 Cu1 134.0(3) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
N1 C9 C10 111.7(3) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N3 C10 C9 111.0(3) . . ?
N3 C10 H10A 109.4 . . ?
N3 C10 H10B 109.4 . . ?
C12 C11 C14 131.1(4) . . ?
N3 C11 C12 106.6(4) . . ?
N3 C11 C14 122.2(5) . . ?
C11 C12 H12 126.4 . . ?
C11 C12 C13 107.2(4) . . ?
C13 C12 H12 126.4 . . ?
N4 C13 C12 108.9(4) . . ?
N4 C13 C15 122.6(3) . . ?
C12 C13 C15 128.4(4) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
N1 C16 H16A 108.9 . . ?
N1 C16 H16B 108.9 . . ?
N1 C16 C17 113.3(3) . . ?
N5 C17 C16 112.6(3) . . ?
N5 C17 H17A 109.1 . . ?
N5 C17 H17B 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
N5 C18 C21 122.6(4) . . ?
C19 C18 N5 106.5(4) . . ?
C19 C18 C21 130.8(3) . . ?
C18 C19 H19 126.7 . . ?
C18 C19 C20 106.7(3) . . ?
C20 C19 H19 126.7 . . ?
N6 C20 C19 110.0(4) . . ?
N6 C20 C22 122.1(3) . . ?
C19 C20 C22 127.9(4) . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 N2 Cu1 115.4(2) . . ?
C6 N2 C2 118.3(3) . . ?
C6 N2 Cu1 126.0(2) . . ?
N4 Cu1 N6 97.31(11) . . ?
N4 Cu1 N1 92.93(13) . . ?
N4 Cu1 Cl1 91.01(10) . . ?
N6 Cu1 Cl1 108.48(9) . . ?
N2 Cu1 N4 166.34(12) . . ?
N2 Cu1 N6 95.17(11) . . ?
N2 Cu1 N1 79.98(12) . . ?
N2 Cu1 Cl1 90.29(9) . . ?
N1 Cu1 N6 97.17(12) . . ?
N1 Cu1 Cl1 153.33(8) . . ?
C1 N1 Cu1 105.0(2) . . ?
C9 N1 C1 108.9(3) . . ?
C9 N1 C16 109.1(3) . . ?
C9 N1 Cu1 115.0(2) . . ?
C16 N1 C1 106.5(3) . . ?
C16 N1 Cu1 111.9(2) . . ?
C3 O1 C7 113.3(3) . . ?
C4 O2 C8 116.4(3) . . ?
N4 N3 C10 119.6(3) . . ?
C11 N3 N4 110.8(4) . . ?
C11 N3 C10 129.5(3) . . ?
O4 Cl2A O5 109.0(6) . . ?
O6A Cl2A O4 99.0(7) . . ?
O6A Cl2A O5 102.5(7) . . ?
O7A Cl2A O4 114.9(7) . . ?
O7A Cl2A O5 117.8(7) . . ?
O7A Cl2A O6A 111.3(9) . . ?
O4 Cl2B O5 117.3(7) . . ?
O4 Cl2B O6B 114.8(8) . . ?
O4 Cl2B O7B 107.0(8) . . ?
O5 Cl2B O6B 105.4(8) . . ?
O5 Cl2B O7B 100.3(8) . . ?
O7B Cl2B O6B 111.1(9) . . ?
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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.497(5) . ?
C1 N1 1.495(4) . ?
C2 C3 1.377(5) . ?
C2 N2 1.361(5) . ?
C3 C4 1.400(5) . ?
C3 O1 1.381(4) . ?
C4 C5 1.388(5) . ?
C4 O2 1.350(4) . ?
O4 Cl2A 1.432(9) . ?
O4 Cl2B 1.350(11) . ?
N4 C13 1.347(5) . ?
N4 Cu1 1.997(3) . ?
N4 N3 1.369(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(5) . ?
O5 Cl2A 1.454(9) . ?
O5 Cl2B 1.401(12) . ?
N5 N6 1.369(5) . ?
N5 C17 1.448(5) . ?
N5 C18 1.369(4) . ?
C6 H6 0.9500 . ?
C6 N2 1.338(5) . ?
N6 C20 1.345(5) . ?
N6 Cu1 2.246(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 O1 1.441(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 O2 1.447(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.519(6) . ?
C9 N1 1.488(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 N3 1.456(5) . ?
C11 C12 1.373(7) . ?
C11 C14 1.497(6) . ?
C11 N3 1.355(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.400(6) . ?
C13 C15 1.490(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.529(5) . ?
C16 N1 1.495(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.367(6) . ?
C18 C21 1.495(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.408(6) . ?
C20 C22 1.485(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N2 Cu1 1.995(3) . ?
Cu1 N1 2.134(3) . ?
Cu1 Cl1 2.3023(11) . ?
O6A Cl2A 1.419(11) . ?
Cl2A O7A 1.396(11) . ?
O6B Cl2B 1.449(11) . ?
Cl2B O7B 1.401(13) . ?
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 C2 C3 C4 178.6(3) . . . . ?
C1 C2 C3 O1 -2.3(5) . . . . ?
C1 C2 N2 C6 -178.0(3) . . . . ?
C1 C2 N2 Cu1 -3.5(4) . . . . ?
C2 C1 N1 C9 161.9(3) . . . . ?
C2 C1 N1 C16 -80.5(4) . . . . ?
C2 C1 N1 Cu1 38.3(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C2 C3 C4 O2 177.7(3) . . . . ?
C2 C3 O1 C7 100.8(4) . . . . ?
C3 C2 N2 C6 0.2(5) . . . . ?
C3 C2 N2 Cu1 174.8(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C3 C4 O2 C8 -178.9(3) . . . . ?
C4 C3 O1 C7 -80.2(4) . . . . ?
C4 C5 C6 N2 0.6(6) . . . . ?
C5 C4 O2 C8 -0.7(5) . . . . ?
C5 C6 N2 C2 -0.8(5) . . . . ?
C5 C6 N2 Cu1 -174.7(3) . . . . ?
N5 N6 C20 C19 -0.1(4) . . . . ?
N5 N6 C20 C22 179.5(3) . . . . ?
N5 C18 C19 C20 -0.7(4) . . . . ?
N6 N5 C17 C16 69.5(4) . . . . ?
N6 N5 C18 C19 0.7(4) . . . . ?
N6 N5 C18 C21 -176.6(3) . . . . ?
C9 C10 N3 N4 58.6(4) . . . . ?
C9 C10 N3 C11 -118.7(4) . . . . ?
C10 C9 N1 C1 -85.8(4) . . . . ?
C10 C9 N1 C16 158.4(3) . . . . ?
C10 C9 N1 Cu1 31.7(4) . . . . ?
C11 C12 C13 N4 -0.4(4) . . . . ?
C11 C12 C13 C15 179.5(4) . . . . ?
C12 C11 N3 N4 1.1(4) . . . . ?
C12 C11 N3 C10 178.6(4) . . . . ?
C13 N4 N3 C10 -179.1(3) . . . . ?
C13 N4 N3 C11 -1.3(4) . . . . ?
C14 C11 C12 C13 176.8(4) . . . . ?
C14 C11 N3 N4 -176.4(3) . . . . ?
C14 C11 N3 C10 1.1(6) . . . . ?
C17 N5 N6 C20 174.8(3) . . . . ?
C17 N5 N6 Cu1 -24.1(4) . . . . ?
C17 N5 C18 C19 -174.0(3) . . . . ?
C17 N5 C18 C21 8.8(5) . . . . ?
C17 C16 N1 C1 163.9(3) . . . . ?
C17 C16 N1 C9 -78.8(4) . . . . ?
C17 C16 N1 Cu1 49.6(3) . . . . ?
C18 N5 N6 C20 -0.4(4) . . . . ?
C18 N5 N6 Cu1 160.8(2) . . . . ?
C18 N5 C17 C16 -116.3(4) . . . . ?
C18 C19 C20 N6 0.5(4) . . . . ?
C18 C19 C20 C22 -179.1(4) . . . . ?
C21 C18 C19 C20 176.3(4) . . . . ?
N2 C2 C3 C4 0.5(5) . . . . ?
N2 C2 C3 O1 179.5(3) . . . . ?
Cu1 N4 C13 C12 175.3(3) . . . . ?
Cu1 N4 C13 C15 -4.5(6) . . . . ?
Cu1 N4 N3 C10 5.7(4) . . . . ?
Cu1 N4 N3 C11 -176.5(2) . . . . ?
Cu1 N6 C20 C19 -156.4(3) . . . . ?
Cu1 N6 C20 C22 23.2(6) . . . . ?
N1 C1 C2 C3 156.6(3) . . . . ?
N1 C1 C2 N2 -25.1(4) . . . . ?
N1 C9 C10 N3 -78.7(4) . . . . ?
N1 C16 C17 N5 -86.1(4) . . . . ?
O1 C3 C4 C5 -179.6(3) . . . . ?
O1 C3 C4 O2 -1.3(5) . . . . ?
O2 C4 C5 C6 -178.1(3) . . . . ?
N3 N4 C13 C12 1.0(4) . . . . ?
N3 N4 C13 C15 -178.8(3) . . . . ?
N3 C11 C12 C13 -0.4(4) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.716 562.9 190.3 ?
2 0.500 0.500 -0.086 562.9 190.3 ?
