#------------------------------------------------------------------------------
#$Date: 2022-03-04 02:23:37 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273298 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/65/1566548.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_1566548
loop_
_publ_author_name
'Wittmann, Christopher'
'Bacher, Felix'
'Enyedy, Eva A.'
'Dömötör, Orsolya'
'Spengler, Gabriella'
'Madejski, Christian'
'Reynisson, Jóhannes'
'Arion, Vladimir B.'
_publ_section_title
;
 Highly Antiproliferative Latonduine and Indolo[2,3-c]quinoline
 Derivatives: Complex Formation with Copper(II) Markedly Changes the
 Kinase Inhibitory Profile.
;
_journal_issue                   3
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              2238
_journal_page_last               2261
_journal_paper_doi               10.1021/acs.jmedchem.1c01740
_journal_volume                  65
_journal_year                    2022
_chemical_formula_moiety         'C33 H39 Cl Cu N8 O3'
_chemical_formula_sum            'C33 H39 Cl Cu N8 O3'
_chemical_formula_weight         694.71
_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
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 118.948(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.667(6)
_cell_length_b                   10.5159(16)
_cell_length_c                   19.220(3)
_cell_measurement_reflns_used    3456
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.564
_cell_measurement_theta_min      3.034
_cell_volume                     6661.9(18)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            58820
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.033
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  0.9436
_exptl_absorpt_correction_T_min  0.8917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             2904
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6523
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0457
_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)+(0.0431P)²+14.3083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4437
_reflns_number_total             6523
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jm1c01740_si_010.cif
_cod_data_source_block           chwi055
_cod_original_cell_volume        6662.0(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1566548
_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   0.892
_shelx_estimated_absorpt_t_max   0.944
_shelxl_version_number           2014-3
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
Cu Cu 0.27602(2) 0.40646(3) 0.43243(2) 0.02412(12) Uani 1 1 d . . . . .
Cl Cl 0.30140(2) 0.58015(7) 0.50753(5) 0.0365(2) Uani 1 1 d . . . . .
C1 C 0.44916(9) 0.2228(3) 0.55604(19) 0.0357(8) Uani 1 1 d . . . . .
H1 H 0.4608 0.1453 0.5513 0.043 Uiso 1 1 calc R U . . .
C2 C 0.46861(10) 0.2924(4) 0.6259(2) 0.0485(10) Uani 1 1 d . . . . .
H2 H 0.4934 0.2624 0.6686 0.058 Uiso 1 1 calc R U . . .
C3 C 0.45198(11) 0.4051(4) 0.6336(2) 0.0523(10) Uani 1 1 d . . . . .
H3 H 0.4652 0.4526 0.6816 0.063 Uiso 1 1 calc R U . . .
C4 C 0.41604(10) 0.4484(3) 0.5713(2) 0.0386(8) Uani 1 1 d . . . . .
H4 H 0.4046 0.5258 0.5768 0.046 Uiso 1 1 calc R U . . .
C4A C 0.39626(9) 0.3805(3) 0.50049(19) 0.0279(7) Uani 1 1 d . . . . .
C5 C 0.35743(8) 0.4277(3) 0.43184(19) 0.0290(7) Uani 1 1 d . . . . .
H5A H 0.3532 0.5175 0.4414 0.035 Uiso 1 1 calc R U . . .
H5B H 0.3598 0.4245 0.3827 0.035 Uiso 1 1 calc R U . . .
N6 N 0.32219(7) 0.3522(2) 0.42021(14) 0.0242(5) Uani 1 1 d . . . . .
C7 C 0.31758(8) 0.2354(3) 0.39169(16) 0.0229(6) Uani 1 1 d . . . . .
C7A C 0.34863(8) 0.1735(3) 0.37820(17) 0.0250(7) Uani 1 1 d . . . . .
N8 N 0.33838(7) 0.0796(2) 0.32252(14) 0.0274(6) Uani 1 1 d . . . . .
H8 H 0.3135 0.0544 0.2895 0.033 Uiso 1 1 calc R U . . .
C8A C 0.37289(9) 0.0309(3) 0.32623(17) 0.0271(7) Uani 1 1 d . . . . .
C9 C 0.37715(10) -0.0648(3) 0.28047(19) 0.0344(8) Uani 1 1 d . . . . .
H9 H 0.3541 -0.1074 0.2402 0.041 Uiso 1 1 calc R U . . .
C10 C 0.41555(10) -0.0950(3) 0.2956(2) 0.0409(8) Uani 1 1 d . . . . .
H10 H 0.4194 -0.1606 0.2658 0.049 Uiso 1 1 calc R U . . .
C11 C 0.44947(10) -0.0304(3) 0.3546(2) 0.0416(9) Uani 1 1 d . . . . .
H11 H 0.4758 -0.0517 0.3630 0.050 Uiso 1 1 calc R U . . .
C12 C 0.44555(9) 0.0625(3) 0.4005(2) 0.0346(8) Uani 1 1 d . . . . .
H12 H 0.4688 0.1044 0.4405 0.042 Uiso 1 1 calc R U . . .
C12A C 0.40652(9) 0.0949(3) 0.38734(17) 0.0267(7) Uani 1 1 d . . . . .
C12B C 0.39059(8) 0.1866(3) 0.42105(17) 0.0256(7) Uani 1 1 d . . . . .
C12C C 0.41278(8) 0.2650(3) 0.49261(17) 0.0264(7) Uani 1 1 d . . . . .
N13 N 0.28450(7) 0.1630(2) 0.37380(14) 0.0237(5) Uani 1 1 d . . . . .
N14 N 0.25932(7) 0.2335(2) 0.39097(13) 0.0222(5) Uani 1 1 d . . . . .
C15 C 0.22524(9) 0.1932(3) 0.38308(16) 0.0247(7) Uani 1 1 d . . . . .
H15 H 0.2153 0.1101 0.3647 0.030 Uiso 1 1 calc R U . . .
C16 C 0.20320(8) 0.2844(3) 0.40443(16) 0.0220(6) Uani 1 1 d . . . . .
N17 N 0.22186(7) 0.3988(2) 0.42969(14) 0.0237(5) Uani 1 1 d . . . . .
C18 C 0.20423(9) 0.4886(3) 0.45178(17) 0.0269(7) Uani 1 1 d . . . . .
H18 H 0.2175 0.5684 0.4689 0.032 Uiso 1 1 calc R U . . .
C19 C 0.16746(9) 0.4711(3) 0.45100(17) 0.0260(7) Uani 1 1 d . . . . .
C20 C 0.14813(9) 0.3546(3) 0.42386(17) 0.0268(7) Uani 1 1 d . . . . .
H20 H 0.1226 0.3395 0.4212 0.032 Uiso 1 1 calc R U . . .
C21 C 0.16599(8) 0.2608(3) 0.40077(16) 0.0244(7) Uani 1 1 d . . . . .
H21 H 0.1530 0.1809 0.3826 0.029 Uiso 1 1 calc R U . . .
C22 C 0.15184(9) 0.5730(3) 0.48461(18) 0.0283(7) Uani 1 1 d . . . . .
H22A H 0.1595 0.5509 0.5402 0.034 Uiso 1 1 calc R U . . .
H22B H 0.1651 0.6547 0.4854 0.034 Uiso 1 1 calc R U . . .
N23 N 0.10809(7) 0.5894(2) 0.43969(15) 0.0298(6) Uani 1 1 d . . . . .
C24 C 0.09435(10) 0.6720(3) 0.4834(2) 0.0384(8) Uani 1 1 d . . . . .
H24A H 0.1078 0.7560 0.4924 0.046 Uiso 1 1 calc R U . . .
H24B H 0.1019 0.6339 0.5358 0.046 Uiso 1 1 calc R U . . .
C25 C 0.04903(11) 0.6884(4) 0.4366(3) 0.0577(11) Uani 1 1 d . . . . .
H25A H 0.0358 0.6050 0.4317 0.069 Uiso 1 1 calc R U . . .
H25B H 0.0402 0.7463 0.4658 0.069 Uiso 1 1 calc R U . . .
O26 O 0.03621(7) 0.7382(3) 0.35952(18) 0.0635(8) Uani 1 1 d . . . . .
C27 C 0.04998(11) 0.6578(4) 0.3177(2) 0.0591(11) Uani 1 1 d . . . . .
H27A H 0.0414 0.6938 0.2643 0.071 Uiso 1 1 calc R U . . .
H27B H 0.0374 0.5728 0.3106 0.071 Uiso 1 1 calc R U . . .
C28 C 0.09556(10) 0.6443(4) 0.36189(19) 0.0418(9) Uani 1 1 d . . . . .
H28A H 0.1044 0.5889 0.3315 0.050 Uiso 1 1 calc R U . . .
H28B H 0.1084 0.7287 0.3679 0.050 Uiso 1 1 calc R U . . .
N1 N 0.24640(8) 0.3362(3) 0.19893(15) 0.0348(6) Uani 1 1 d . . . . .
O1 O 0.23795(6) 0.4682(2) 0.28385(12) 0.0343(5) Uani 1 1 d . . . . .
C29 C 0.25670(10) 0.4330(3) 0.24882(19) 0.0336(8) Uani 1 1 d . . . . .
H29 H 0.2803 0.4796 0.2587 0.040 Uiso 1 1 calc R U . . .
C30 C 0.27018(12) 0.3028(4) 0.1602(2) 0.0499(10) Uani 1 1 d . . . . .
H30A H 0.2940 0.3583 0.1799 0.075 Uiso 1 1 calc R U . . .
H30B H 0.2535 0.3137 0.1026 0.075 Uiso 1 1 calc R U . . .
H30C H 0.2790 0.2141 0.1720 0.075 Uiso 1 1 calc R U . . .
C31 C 0.21090(10) 0.2589(3) 0.1808(2) 0.0428(9) Uani 1 1 d . . . . .
H31A H 0.1986 0.2881 0.2127 0.064 Uiso 1 1 calc R U . . .
H31B H 0.2190 0.1697 0.1933 0.064 Uiso 1 1 calc R U . . .
H31C H 0.1912 0.2669 0.1242 0.064 Uiso 1 1 calc R U . . .
N2 N 0.41842(12) 0.4961(4) 0.3273(2) 0.0727(11) Uani 1 1 d D . . . .
C32 C 0.3917(3) 0.5893(10) 0.3211(7) 0.1000(15) Uani 0.5 1 d D . P A 2
H32 H 0.4013 0.6510 0.3623 0.120 Uiso 0.5 1 calc R U P A 2
C33 C 0.3817(3) 0.4777(11) 0.2624(7) 0.1000(15) Uani 0.5 1 d D . P A 1
H33 H 0.3786 0.4117 0.2261 0.120 Uiso 0.5 1 calc R U P A 1
O2 O 0.3566(2) 0.6013(7) 0.2677(4) 0.0788(14) Uiso 0.5 1 d D . P A 2
C34 C 0.4310(4) 0.5891(10) 0.3889(6) 0.1000(15) Uani 0.5 1 d D . P A 1
H34A H 0.4076 0.6397 0.3812 0.150 Uiso 0.5 1 calc R U P A 1
H34B H 0.4514 0.6449 0.3872 0.150 Uiso 0.5 1 calc R U P A 1
H34C H 0.4428 0.5463 0.4407 0.150 Uiso 0.5 1 calc R U P A 1
C36 C 0.4498(3) 0.4041(10) 0.3396(8) 0.1000(15) Uani 0.5 1 d D . P A 1
H36A H 0.4418 0.3574 0.2901 0.150 Uiso 0.5 1 calc R U P A 1
H36B H 0.4532 0.3444 0.3815 0.150 Uiso 0.5 1 calc R U P A 1
H36C H 0.4754 0.4486 0.3555 0.150 Uiso 0.5 1 calc R U P A 1
C37 C 0.4043(4) 0.4032(10) 0.2656(6) 0.1000(15) Uani 0.5 1 d D . P A 2
H37A H 0.4130 0.4263 0.2269 0.150 Uiso 0.5 1 calc R U P A 2
H37B H 0.3746 0.3996 0.2391 0.150 Uiso 0.5 1 calc R U P A 2
H37C H 0.4154 0.3198 0.2885 0.150 Uiso 0.5 1 calc R U P A 2
C35 C 0.4570(3) 0.4869(12) 0.3977(6) 0.1000(15) Uani 0.5 1 d D . P A 2
H35A H 0.4785 0.5108 0.3854 0.150 Uiso 0.5 1 calc R U P A 2
H35B H 0.4613 0.3992 0.4175 0.150 Uiso 0.5 1 calc R U P A 2
H35C H 0.4576 0.5442 0.4384 0.150 Uiso 0.5 1 calc R U P A 2
O3 O 0.3531(2) 0.5427(7) 0.2496(4) 0.0788(14) Uiso 0.5 1 d D . P A 1
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'
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'
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
N6 Cu N14 78.99(10) . . ?
N6 Cu N17 159.27(10) . . ?
N14 Cu N17 80.28(9) . . ?
N6 Cu Cl 100.92(7) . . ?
N14 Cu Cl 166.40(7) . . ?
N17 Cu Cl 99.23(7) . . ?
C2 C1 C12C 120.9(3) . . ?
C2 C1 H1 119.5 . . ?
C12C C1 H1 119.5 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C4A 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C4A C4 H4 119.5 . . ?
C4 C4A C12C 119.6(3) . . ?
C4 C4A C5 121.5(3) . . ?
C12C C4A C5 118.9(3) . . ?
N6 C5 C4A 112.3(2) . . ?
N6 C5 H5A 109.1 . . ?
C4A C5 H5A 109.1 . . ?
N6 C5 H5B 109.1 . . ?
C4A C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C7 N6 C5 119.5(2) . . ?
C7 N6 Cu 112.11(18) . . ?
C5 N6 Cu 128.10(19) . . ?
N6 C7 N13 123.2(2) . . ?
N6 C7 C7A 122.0(3) . . ?
N13 C7 C7A 114.8(3) . . ?
N8 C7A C12B 110.1(2) . . ?
N8 C7A C7 120.8(3) . . ?
C12B C7A C7 128.8(3) . . ?
C8A N8 C7A 109.2(2) . . ?
C8A N8 H8 125.4 . . ?
C7A N8 H8 125.4 . . ?
N8 C8A C9 129.3(3) . . ?
N8 C8A C12A 108.2(3) . . ?
C9 C8A C12A 122.5(3) . . ?
C10 C9 C8A 117.8(3) . . ?
C10 C9 H9 121.1 . . ?
C8A C9 H9 121.1 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C12A 119.1(3) . . ?
C11 C12 H12 120.5 . . ?
C12A C12 H12 120.5 . . ?
C12 C12A C8A 118.1(3) . . ?
C12 C12A C12B 134.9(3) . . ?
C8A C12A C12B 106.9(2) . . ?
C7A C12B C12A 105.5(3) . . ?
C7A C12B C12C 125.4(3) . . ?
C12A C12B C12C 128.5(3) . . ?
C1 C12C C4A 118.6(3) . . ?
C1 C12C C12B 120.9(3) . . ?
C4A C12C C12B 120.3(3) . . ?
C7 N13 N14 107.1(2) . . ?
C15 N14 N13 124.2(2) . . ?
C15 N14 Cu 117.2(2) . . ?
N13 N14 Cu 118.56(17) . . ?
N14 C15 C16 115.0(3) . . ?
N14 C15 H15 122.5 . . ?
C16 C15 H15 122.5 . . ?
N17 C16 C21 120.7(3) . . ?
N17 C16 C15 114.7(2) . . ?
C21 C16 C15 124.6(3) . . ?
C18 N17 C16 119.2(2) . . ?
C18 N17 Cu 128.0(2) . . ?
C16 N17 Cu 112.73(18) . . ?
N17 C18 C19 123.3(3) . . ?
N17 C18 H18 118.4 . . ?
C19 C18 H18 118.4 . . ?
C18 C19 C20 117.3(3) . . ?
C18 C19 C22 119.6(3) . . ?
C20 C19 C22 122.9(3) . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C16 C21 H21 120.3 . . ?
N23 C22 C19 113.2(2) . . ?
N23 C22 H22A 108.9 . . ?
C19 C22 H22A 108.9 . . ?
N23 C22 H22B 108.9 . . ?
C19 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C28 N23 C22 111.6(2) . . ?
C28 N23 C24 109.0(3) . . ?
C22 N23 C24 110.1(2) . . ?
N23 C24 C25 109.8(3) . . ?
N23 C24 H24A 109.7 . . ?
C25 C24 H24A 109.7 . . ?
N23 C24 H24B 109.7 . . ?
C25 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
O26 C25 C24 112.4(3) . . ?
O26 C25 H25A 109.1 . . ?
C24 C25 H25A 109.1 . . ?
O26 C25 H25B 109.1 . . ?
C24 C25 H25B 109.1 . . ?
H25A C25 H25B 107.9 . . ?
C25 O26 C27 109.7(3) . . ?
O26 C27 C28 111.3(3) . . ?
O26 C27 H27A 109.4 . . ?
C28 C27 H27A 109.4 . . ?
O26 C27 H27B 109.4 . . ?
C28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
N23 C28 C27 109.3(3) . . ?
N23 C28 H28A 109.8 . . ?
C27 C28 H28A 109.8 . . ?
N23 C28 H28B 109.8 . . ?
C27 C28 H28B 109.8 . . ?
H28A C28 H28B 108.3 . . ?
C29 N1 C31 121.1(3) . . ?
C29 N1 C30 121.3(3) . . ?
C31 N1 C30 117.6(3) . . ?
O1 C29 N1 125.3(3) . . ?
O1 C29 H29 117.4 . . ?
N1 C29 H29 117.4 . . ?
N1 C30 H30A 109.5 . . ?
N1 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N1 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N1 C31 H31A 109.5 . . ?
N1 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N1 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 N2 C37 117.1(8) . . ?
C33 N2 C34 130.0(7) . . ?
C32 N2 C35 119.9(8) . . ?
C37 N2 C35 122.7(7) . . ?
C33 N2 C36 116.2(8) . . ?
C34 N2 C36 113.7(8) . . ?
O2 C32 N2 126.7(10) . . ?
O2 C32 H32 116.7 . . ?
N2 C32 H32 116.7 . . ?
O3 C33 N2 121.5(10) . . ?
O3 C33 H33 119.2 . . ?
N2 C33 H33 119.2 . . ?
N2 C34 H34A 109.5 . . ?
N2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N2 C36 H36A 109.5 . . ?
N2 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N2 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N2 C37 H37A 109.5 . . ?
N2 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N2 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N2 C35 H35A 109.5 . . ?
N2 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N2 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
Cu N6 1.949(2) . ?
Cu N14 1.963(2) . ?
Cu N17 2.017(2) . ?
Cu Cl 2.2355(9) . ?
C1 C2 1.387(5) . ?
C1 C12C 1.394(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.391(4) . ?
C4 H4 0.9500 . ?
C4A C12C 1.406(4) . ?
C4A C5 1.503(4) . ?
C5 N6 1.468(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N6 C7 1.321(4) . ?
C7 N13 1.355(4) . ?
C7 C7A 1.467(4) . ?
C7A N8 1.368(4) . ?
C7A C12B 1.391(4) . ?
N8 C8A 1.366(4) . ?
N8 H8 0.8800 . ?
C8A C9 1.396(4) . ?
C8A C12A 1.413(4) . ?
C9 C10 1.368(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9500 . ?
C12 C12A 1.408(4) . ?
C12 H12 0.9500 . ?
C12A C12B 1.444(4) . ?
C12B C12C 1.468(4) . ?
N13 N14 1.364(3) . ?
N14 C15 1.289(3) . ?
C15 C16 1.452(4) . ?
C15 H15 0.9500 . ?
C16 N17 1.359(4) . ?
C16 C21 1.391(4) . ?
N17 C18 1.336(4) . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(4) . ?
C19 C22 1.510(4) . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N23 1.454(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 C28 1.452(4) . ?
N23 C24 1.466(4) . ?
C24 C25 1.505(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O26 1.417(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
O26 C27 1.427(4) . ?
C27 C28 1.509(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
N1 C29 1.322(4) . ?
N1 C31 1.455(4) . ?
N1 C30 1.458(4) . ?
O1 C29 1.245(4) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
N2 C33 1.355(9) . ?
N2 C32 1.367(9) . ?
N2 C37 1.425(8) . ?
N2 C34 1.428(8) . ?
N2 C35 1.431(8) . ?
N2 C36 1.454(7) . ?
C32 O2 1.227(8) . ?
C32 H32 0.9500 . ?
C33 O3 1.198(8) . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
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
C5 H5A Cl 0.99 2.87 3.481(3) 120.5 .
N8 H8 O1 0.88 1.98 2.851(3) 169.8 4_545
C15 H15 O3 0.95 2.55 3.230(8) 129.0 4_545
C18 H18 Cl 0.95 2.88 3.417(3) 117.1 .
C31 H31B O1 0.98 2.57 3.500(4) 157.9 4_545
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
C12C C1 C2 C3 0.1(6) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C4A -0.2(6) . . . . ?
C3 C4 C4A C12C 0.9(5) . . . . ?
C3 C4 C4A C5 -179.1(3) . . . . ?
C4 C4A C5 N6 -108.1(3) . . . . ?
C12C C4A C5 N6 71.8(3) . . . . ?
C4A C5 N6 C7 -71.7(3) . . . . ?
C4A C5 N6 Cu 114.6(2) . . . . ?
C5 N6 C7 N13 -175.1(2) . . . . ?
Cu N6 C7 N13 -0.4(3) . . . . ?
C5 N6 C7 C7A 6.0(4) . . . . ?
Cu N6 C7 C7A -179.3(2) . . . . ?
N6 C7 C7A N8 -154.1(3) . . . . ?
N13 C7 C7A N8 26.9(4) . . . . ?
N6 C7 C7A C12B 33.3(5) . . . . ?
N13 C7 C7A C12B -145.7(3) . . . . ?
C12B C7A N8 C8A -1.2(3) . . . . ?
C7 C7A N8 C8A -175.1(3) . . . . ?
C7A N8 C8A C9 -179.2(3) . . . . ?
C7A N8 C8A C12A 0.9(3) . . . . ?
N8 C8A C9 C10 179.1(3) . . . . ?
C12A C8A C9 C10 -0.9(5) . . . . ?
C8A C9 C10 C11 -0.8(5) . . . . ?
C9 C10 C11 C12 1.7(5) . . . . ?
C10 C11 C12 C12A -0.7(5) . . . . ?
C11 C12 C12A C8A -0.9(5) . . . . ?
C11 C12 C12A C12B -178.3(3) . . . . ?
N8 C8A C12A C12 -178.2(3) . . . . ?
C9 C8A C12A C12 1.8(5) . . . . ?
N8 C8A C12A C12B -0.2(3) . . . . ?
C9 C8A C12A C12B 179.9(3) . . . . ?
N8 C7A C12B C12A 1.1(3) . . . . ?
C7 C7A C12B C12A 174.3(3) . . . . ?
N8 C7A C12B C12C -170.9(3) . . . . ?
C7 C7A C12B C12C 2.3(5) . . . . ?
C12 C12A C12B C7A 177.1(3) . . . . ?
C8A C12A C12B C7A -0.5(3) . . . . ?
C12 C12A C12B C12C -11.3(6) . . . . ?
C8A C12A C12B C12C 171.1(3) . . . . ?
C2 C1 C12C C4A 0.6(5) . . . . ?
C2 C1 C12C C12B -175.2(3) . . . . ?
C4 C4A C12C C1 -1.1(4) . . . . ?
C5 C4A C12C C1 178.9(3) . . . . ?
C4 C4A C12C C12B 174.8(3) . . . . ?
C5 C4A C12C C12B -5.2(4) . . . . ?
C7A C12B C12C C1 140.9(3) . . . . ?
C12A C12B C12C C1 -29.2(5) . . . . ?
C7A C12B C12C C4A -34.9(4) . . . . ?
C12A C12B C12C C4A 155.1(3) . . . . ?
N6 C7 N13 N14 -0.1(4) . . . . ?
C7A C7 N13 N14 179.0(2) . . . . ?
C7 N13 N14 C15 -178.2(2) . . . . ?
C7 N13 N14 Cu 0.5(3) . . . . ?
N13 N14 C15 C16 -179.7(2) . . . . ?
Cu N14 C15 C16 1.6(3) . . . . ?
N14 C15 C16 N17 -0.1(4) . . . . ?
N14 C15 C16 C21 -179.7(3) . . . . ?
C21 C16 N17 C18 0.6(4) . . . . ?
C15 C16 N17 C18 -179.1(2) . . . . ?
C21 C16 N17 Cu 178.3(2) . . . . ?
C15 C16 N17 Cu -1.4(3) . . . . ?
C16 N17 C18 C19 0.5(4) . . . . ?
Cu N17 C18 C19 -176.8(2) . . . . ?
N17 C18 C19 C20 -1.6(4) . . . . ?
N17 C18 C19 C22 174.0(3) . . . . ?
C18 C19 C20 C21 1.5(4) . . . . ?
C22 C19 C20 C21 -173.9(3) . . . . ?
C19 C20 C21 C16 -0.5(4) . . . . ?
N17 C16 C21 C20 -0.6(4) . . . . ?
C15 C16 C21 C20 179.0(3) . . . . ?
C18 C19 C22 N23 142.4(3) . . . . ?
C20 C19 C22 N23 -42.4(4) . . . . ?
C19 C22 N23 C28 -69.1(3) . . . . ?
C19 C22 N23 C24 169.7(2) . . . . ?
C28 N23 C24 C25 57.3(4) . . . . ?
C22 N23 C24 C25 -179.9(3) . . . . ?
N23 C24 C25 O26 -57.2(4) . . . . ?
C24 C25 O26 C27 56.9(4) . . . . ?
C25 O26 C27 C28 -58.0(4) . . . . ?
C22 N23 C28 C27 179.4(3) . . . . ?
C24 N23 C28 C27 -58.8(4) . . . . ?
O26 C27 C28 N23 60.0(4) . . . . ?
C31 N1 C29 O1 -0.5(5) . . . . ?
C30 N1 C29 O1 179.5(3) . . . . ?
C33 N2 C32 O2 -2.3(11) . . . . ?
C37 N2 C32 O2 0.1(15) . . . . ?
C34 N2 C32 O2 -178.2(15) . . . . ?
C35 N2 C32 O2 -173.1(10) . . . . ?
C32 N2 C33 O3 -6.2(10) . . . . ?
C37 N2 C33 O3 176.7(17) . . . . ?
C34 N2 C33 O3 -1.5(16) . . . . ?
C35 N2 C33 O3 133(3) . . . . ?
C36 N2 C33 O3 174.8(10) . . . . ?
