#------------------------------------------------------------------------------
#$Date: 2022-03-04 02:22:00 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/65/1566544.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_1566544
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         'C28 H28 Br Cl Cu N6 O2'
_chemical_formula_sum            'C28 H28 Br Cl Cu N6 O2'
_chemical_formula_weight         659.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 103.8245(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1127(6)
_cell_length_b                   8.9758(3)
_cell_length_c                   19.2463(7)
_cell_measurement_reflns_used    9776
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.944
_cell_measurement_theta_min      2.517
_cell_volume                     2702.85(17)
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT v8.38A'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            101495
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.040
_diffrn_reflns_theta_min         2.256
_exptl_absorpt_coefficient_mu    2.424
_exptl_absorpt_correction_T_max  0.8987
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       block
_exptl_crystal_F_000             1340
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         7900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0287
_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)+(0.0299P)²+2.0794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6709
_reflns_number_total             7900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jm1c01740_si_016.cif
_cod_data_source_block           feba589
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566544
_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   0.665
_shelx_estimated_absorpt_t_max   0.899
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br Br -0.55096(2) 0.22197(2) 0.31097(2) 0.03109(6) Uani 1 1 d . . . . .
Cu Cu 0.01177(2) 0.15456(2) 0.13548(2) 0.01659(5) Uani 1 1 d . . . . .
Cl Cl 0.04740(3) 0.37144(4) 0.09099(2) 0.02182(8) Uani 1 1 d . . . . .
C1 C -0.34757(11) 0.35414(19) 0.11137(9) 0.0203(3) Uani 1 1 d . . . . .
H1 H -0.3964 0.3027 0.1185 0.024 Uiso 1 1 calc R U . . .
C2 C -0.35642(11) 0.4573(2) 0.05637(9) 0.0239(3) Uani 1 1 d . . . . .
H2 H -0.4114 0.4764 0.0264 0.029 Uiso 1 1 calc R U . . .
C3 C -0.28568(12) 0.5328(2) 0.04472(9) 0.0232(3) Uani 1 1 d . . . . .
H3 H -0.2922 0.6043 0.0074 0.028 Uiso 1 1 calc R U . . .
C4 C -0.20516(11) 0.50295(18) 0.08821(9) 0.0196(3) Uani 1 1 d . . . . .
H4 H -0.1565 0.5533 0.0799 0.024 Uiso 1 1 calc R U . . .
C4A C -0.19519(10) 0.40003(18) 0.14370(9) 0.0178(3) Uani 1 1 d . . . . .
C5 C -0.10819(11) 0.36880(18) 0.19142(9) 0.0195(3) Uani 1 1 d . . . . .
H5A H -0.0666 0.4418 0.1811 0.023 Uiso 1 1 calc R U . . .
H5B H -0.1105 0.3813 0.2420 0.023 Uiso 1 1 calc R U . . .
N6 N -0.07910(9) 0.21774(15) 0.18082(8) 0.0186(3) Uani 1 1 d . . . . .
C7 C -0.11538(10) 0.10400(18) 0.20569(8) 0.0177(3) Uani 1 1 d . . . . .
C7A C -0.18731(11) 0.12442(18) 0.23848(9) 0.0180(3) Uani 1 1 d . . . . .
N8 N -0.20137(10) 0.02941(16) 0.29061(8) 0.0211(3) Uani 1 1 d . . . . .
H8 H -0.1660 -0.0401 0.3122 0.025 Uiso 1 1 calc R U . . .
C8A C -0.27978(11) 0.06111(19) 0.30327(9) 0.0212(3) Uani 1 1 d . . . . .
C9 C -0.32067(13) -0.0053(2) 0.35173(10) 0.0268(4) Uani 1 1 d . . . . .
H9 H -0.2938 -0.0823 0.3830 0.032 Uiso 1 1 calc R U . . .
C10 C -0.40096(13) 0.0446(2) 0.35258(10) 0.0280(4) Uani 1 1 d . . . . .
H10 H -0.4309 0.0007 0.3843 0.034 Uiso 1 1 calc R U . . .
C11 C -0.43905(12) 0.1602(2) 0.30676(9) 0.0242(3) Uani 1 1 d . . . . .
C12 C -0.39955(11) 0.2285(2) 0.25913(9) 0.0211(3) Uani 1 1 d . . . . .
H12 H -0.4265 0.3072 0.2291 0.025 Uiso 1 1 calc R U . . .
C12A C -0.31775(11) 0.17723(19) 0.25664(9) 0.0191(3) Uani 1 1 d . . . . .
C12B C -0.25724(11) 0.21782(18) 0.21553(8) 0.0181(3) Uani 1 1 d . . . . .
C12C C -0.26701(10) 0.32525(18) 0.15654(8) 0.0170(3) Uani 1 1 d . . . . .
N13 N -0.09240(9) -0.04029(15) 0.19772(7) 0.0180(3) Uani 1 1 d . . . . .
N14 N -0.03253(9) -0.03915(15) 0.15892(7) 0.0170(3) Uani 1 1 d . . . . .
C15 C -0.00319(11) -0.15774(18) 0.13539(9) 0.0188(3) Uani 1 1 d . . . . .
H15 H -0.0207 -0.2551 0.1450 0.023 Uiso 1 1 calc R U . . .
C16 C 0.05893(11) -0.13074(18) 0.09297(9) 0.0183(3) Uani 1 1 d . . . . .
N17 N 0.07635(9) 0.01590(15) 0.08368(7) 0.0180(3) Uani 1 1 d . . . . .
C18 C 0.13175(11) 0.05069(19) 0.04469(9) 0.0202(3) Uani 1 1 d . . . . .
H18 H 0.1429 0.1529 0.0380 0.024 Uiso 1 1 calc R U . . .
C19 C 0.17412(11) -0.0563(2) 0.01330(9) 0.0203(3) Uani 1 1 d . . . . .
C20 C 0.15616(12) -0.2048(2) 0.02322(9) 0.0234(3) Uani 1 1 d . . . . .
H20 H 0.1841 -0.2806 0.0029 0.028 Uiso 1 1 calc R U . . .
C21 C 0.09769(12) -0.24352(19) 0.06263(9) 0.0219(3) Uani 1 1 d . . . . .
H21 H 0.0844 -0.3451 0.0687 0.026 Uiso 1 1 calc R U . . .
C22 C 0.23829(11) -0.0103(2) -0.02785(9) 0.0234(3) Uani 1 1 d . . . . .
H22A H 0.2606 -0.1002 -0.0470 0.028 Uiso 1 1 calc R U . . .
H22B H 0.2097 0.0526 -0.0689 0.028 Uiso 1 1 calc R U . . .
N23 N 0.30996(9) 0.07300(16) 0.01713(7) 0.0195(3) Uani 1 1 d . . . . .
C24 C 0.37138(11) 0.1076(2) -0.02576(9) 0.0229(3) Uani 1 1 d . . . . .
H24A H 0.3434 0.1699 -0.0672 0.027 Uiso 1 1 calc R U . . .
H24B H 0.3908 0.0142 -0.0442 0.027 Uiso 1 1 calc R U . . .
C25 C 0.44779(12) 0.1901(2) 0.01926(10) 0.0266(4) Uani 1 1 d . . . . .
H25A H 0.4895 0.2095 -0.0100 0.032 Uiso 1 1 calc R U . . .
H25B H 0.4287 0.2874 0.0340 0.032 Uiso 1 1 calc R U . . .
O26 O 0.48847(8) 0.10770(16) 0.08134(7) 0.0276(3) Uani 1 1 d . . . . .
C27 C 0.42848(11) 0.0742(2) 0.12289(9) 0.0245(4) Uani 1 1 d . . . . .
H27A H 0.4071 0.1681 0.1393 0.029 Uiso 1 1 calc R U . . .
H27B H 0.4572 0.0164 0.1657 0.029 Uiso 1 1 calc R U . . .
C28 C 0.35393(11) -0.0146(2) 0.07986(9) 0.0230(3) Uani 1 1 d . . . . .
H28A H 0.3747 -0.1095 0.0640 0.028 Uiso 1 1 calc R U . . .
H28B H 0.3136 -0.0383 0.1099 0.028 Uiso 1 1 calc R U . . .
O1 O 0.12221(7) 0.18186(13) 0.23929(6) 0.0196(2) Uani 1 1 d . . . . .
H100 H 0.1242 0.2655 0.2639 0.029 Uiso 1 1 d R U . . .
C29 C 0.20909(11) 0.1619(2) 0.23614(10) 0.0252(4) Uani 1 1 d . . . . .
H29A H 0.2206 0.2212 0.1967 0.038 Uiso 1 1 calc R U . . .
H29B H 0.2194 0.0564 0.2282 0.038 Uiso 1 1 calc R U . . .
H29C H 0.2469 0.1943 0.2814 0.038 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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
N6 Cu N14 78.66(6) . . ?
N6 Cu N17 157.16(6) . . ?
N14 Cu N17 80.09(6) . . ?
N6 Cu Cl 101.79(4) . . ?
N14 Cu Cl 170.60(4) . . ?
N17 Cu Cl 97.81(4) . . ?
N6 Cu O1 94.92(5) . . ?
N14 Cu O1 98.01(5) . . ?
N17 Cu O1 96.24(5) . . ?
Cl Cu O1 91.32(3) . . ?
C2 C1 C12C 120.47(16) . . ?
C2 C1 H1 119.8 . . ?
C12C C1 H1 119.8 . . ?
C1 C2 C3 120.65(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 119.46(16) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4A C4 C3 120.62(16) . . ?
C4A C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C4A C12C 120.09(15) . . ?
C4 C4A C5 120.73(15) . . ?
C12C C4A C5 119.17(15) . . ?
N6 C5 C4A 111.67(13) . . ?
N6 C5 H5A 109.3 . . ?
C4A C5 H5A 109.3 . . ?
N6 C5 H5B 109.3 . . ?
C4A C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7 N6 C5 118.72(14) . . ?
C7 N6 Cu 112.34(11) . . ?
C5 N6 Cu 128.92(11) . . ?
N6 C7 N13 122.44(15) . . ?
N6 C7 C7A 121.73(15) . . ?
N13 C7 C7A 115.66(14) . . ?
N8 C7A C12B 110.09(15) . . ?
N8 C7A C7 121.61(14) . . ?
C12B C7A C7 127.35(15) . . ?
C8A N8 C7A 108.65(14) . . ?
C8A N8 H8 125.7 . . ?
C7A N8 H8 125.7 . . ?
N8 C8A C9 129.11(16) . . ?
N8 C8A C12A 108.47(15) . . ?
C9 C8A C12A 122.41(17) . . ?
C10 C9 C8A 117.68(17) . . ?
C10 C9 H9 121.2 . . ?
C8A C9 H9 121.2 . . ?
C9 C10 C11 120.35(17) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 122.96(17) . . ?
C12 C11 Br 119.40(14) . . ?
C10 C11 Br 117.63(14) . . ?
C11 C12 C12A 117.55(16) . . ?
C11 C12 H12 121.2 . . ?
C12A C12 H12 121.2 . . ?
C12 C12A C8A 119.03(16) . . ?
C12 C12A C12B 134.25(16) . . ?
C8A C12A C12B 106.72(15) . . ?
C7A C12B C12A 106.05(14) . . ?
C7A C12B C12C 124.81(15) . . ?
C12A C12B C12C 128.94(15) . . ?
C1 C12C C4A 118.68(15) . . ?
C1 C12C C12B 120.83(15) . . ?
C4A C12C C12B 120.48(14) . . ?
N14 N13 C7 107.64(13) . . ?
C15 N14 N13 123.83(14) . . ?
C15 N14 Cu 117.65(12) . . ?
N13 N14 Cu 118.51(10) . . ?
N14 C15 C16 114.74(14) . . ?
N14 C15 H15 122.6 . . ?
C16 C15 H15 122.6 . . ?
N17 C16 C21 121.32(16) . . ?
N17 C16 C15 115.10(14) . . ?
C21 C16 C15 123.57(15) . . ?
C18 N17 C16 119.04(15) . . ?
C18 N17 Cu 128.57(12) . . ?
C16 N17 Cu 112.38(11) . . ?
N17 C18 C19 122.99(16) . . ?
N17 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C20 C19 C18 117.50(16) . . ?
C20 C19 C22 121.96(16) . . ?
C18 C19 C22 120.52(16) . . ?
C21 C20 C19 120.47(16) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 118.65(16) . . ?
C20 C21 H21 120.7 . . ?
C16 C21 H21 120.7 . . ?
N23 C22 C19 111.82(14) . . ?
N23 C22 H22A 109.3 . . ?
C19 C22 H22A 109.3 . . ?
N23 C22 H22B 109.3 . . ?
C19 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C24 N23 C22 108.49(13) . . ?
C24 N23 C28 108.52(13) . . ?
C22 N23 C28 111.54(14) . . ?
N23 C24 C25 110.29(14) . . ?
N23 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
N23 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
O26 C25 C24 111.91(15) . . ?
O26 C25 H25A 109.2 . . ?
C24 C25 H25A 109.2 . . ?
O26 C25 H25B 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C27 O26 C25 110.01(13) . . ?
O26 C27 C28 111.11(15) . . ?
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 109.32(14) . . ?
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 O1 Cu 120.14(10) . . ?
C29 O1 H100 102.6 . . ?
Cu O1 H100 117.9 . . ?
O1 C29 H29A 109.5 . . ?
O1 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O1 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
Br C11 1.9065(19) . ?
Cu N6 1.9590(15) . ?
Cu N14 1.9724(14) . ?
Cu N17 2.0301(14) . ?
Cu Cl 2.2555(4) . ?
Cu O1 2.3493(12) . ?
C1 C2 1.388(2) . ?
C1 C12C 1.403(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C4A 1.392(2) . ?
C4 H4 0.9500 . ?
C4A C12C 1.410(2) . ?
C4A C5 1.507(2) . ?
C5 N6 1.465(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N6 C7 1.322(2) . ?
C7 N13 1.366(2) . ?
C7 C7A 1.458(2) . ?
C7A N8 1.376(2) . ?
C7A C12B 1.389(2) . ?
N8 C8A 1.373(2) . ?
N8 H8 0.8800 . ?
C8A C9 1.397(3) . ?
C8A C12A 1.416(2) . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(2) . ?
C12 C12A 1.408(2) . ?
C12 H12 0.9500 . ?
C12A C12B 1.442(2) . ?
C12B C12C 1.469(2) . ?
N13 N14 1.354(2) . ?
N14 C15 1.290(2) . ?
C15 C16 1.455(2) . ?
C15 H15 0.9500 . ?
C16 N17 1.366(2) . ?
C16 C21 1.389(2) . ?
N17 C18 1.333(2) . ?
C18 C19 1.397(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(2) . ?
C19 C22 1.503(2) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N23 1.471(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 C24 1.466(2) . ?
N23 C28 1.473(2) . ?
C24 C25 1.518(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O26 1.425(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
O26 C27 1.426(2) . ?
C27 C28 1.513(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
O1 C29 1.427(2) . ?
O1 H100 0.8840 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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 2.88 3.5125(19) 122.3 .
N8 H8 Cl 0.88 2.46 3.2644(15) 152.3 2_545
C18 H18 Cl 0.95 2.83 3.3924(18) 118.9 .
C21 H21 Cl 0.95 2.67 3.6208(18) 177.9 1_545
C24 H24B O26 0.99 2.48 3.337(2) 144.4 3_655
C27 H27B Br 0.99 3.02 3.7827(19) 134.3 2_545
O1 H100 N13 0.88 2.01 2.8633(18) 162.6 2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12C C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C4A -0.9(3) . . . . ?
C3 C4 C4A C12C -0.3(2) . . . . ?
C3 C4 C4A C5 -179.28(15) . . . . ?
C4 C4A C5 N6 -112.12(17) . . . . ?
C12C C4A C5 N6 68.8(2) . . . . ?
C4A C5 N6 C7 -72.84(19) . . . . ?
C4A C5 N6 Cu 109.02(15) . . . . ?
C5 N6 C7 N13 179.61(14) . . . . ?
Cu N6 C7 N13 -1.96(19) . . . . ?
C5 N6 C7 C7A 4.6(2) . . . . ?
Cu N6 C7 C7A -177.00(12) . . . . ?
N6 C7 C7A N8 -150.62(16) . . . . ?
N13 C7 C7A N8 34.0(2) . . . . ?
N6 C7 C7A C12B 41.7(2) . . . . ?
N13 C7 C7A C12B -133.70(17) . . . . ?
C12B C7A N8 C8A -1.05(19) . . . . ?
C7 C7A N8 C8A -170.67(15) . . . . ?
C7A N8 C8A C9 -179.50(18) . . . . ?
C7A N8 C8A C12A 1.46(19) . . . . ?
N8 C8A C9 C10 -178.16(18) . . . . ?
C12A C8A C9 C10 0.8(3) . . . . ?
C8A C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C9 C10 C11 Br 179.62(15) . . . . ?
C10 C11 C12 C12A 0.7(3) . . . . ?
Br C11 C12 C12A -178.61(12) . . . . ?
C11 C12 C12A C8A -0.9(2) . . . . ?
C11 C12 C12A C12B 179.96(18) . . . . ?
N8 C8A C12A C12 179.35(15) . . . . ?
C9 C8A C12A C12 0.2(3) . . . . ?
N8 C8A C12A C12B -1.31(19) . . . . ?
C9 C8A C12A C12B 179.57(16) . . . . ?
N8 C7A C12B C12A 0.21(18) . . . . ?
C7 C7A C12B C12A 169.08(16) . . . . ?
N8 C7A C12B C12C -175.04(15) . . . . ?
C7 C7A C12B C12C -6.2(3) . . . . ?
C12 C12A C12B C7A 179.86(18) . . . . ?
C8A C12A C12B C7A 0.67(18) . . . . ?
C12 C12A C12B C12C -5.2(3) . . . . ?
C8A C12A C12B C12C 175.65(16) . . . . ?
C2 C1 C12C C4A -1.7(2) . . . . ?
C2 C1 C12C C12B 179.13(16) . . . . ?
C4 C4A C12C C1 1.6(2) . . . . ?
C5 C4A C12C C1 -179.41(15) . . . . ?
C4 C4A C12C C12B -179.24(15) . . . . ?
C5 C4A C12C C12B -0.2(2) . . . . ?
C7A C12B C12C C1 144.79(17) . . . . ?
C12A C12B C12C C1 -29.3(3) . . . . ?
C7A C12B C12C C4A -34.4(2) . . . . ?
C12A C12B C12C C4A 151.48(17) . . . . ?
N6 C7 N13 N14 -2.8(2) . . . . ?
C7A C7 N13 N14 172.57(13) . . . . ?
C7 N13 N14 C15 -172.72(15) . . . . ?
C7 N13 N14 Cu 6.38(16) . . . . ?
N13 N14 C15 C16 178.19(14) . . . . ?
Cu N14 C15 C16 -0.92(19) . . . . ?
N14 C15 C16 N17 -0.7(2) . . . . ?
N14 C15 C16 C21 -179.72(15) . . . . ?
C21 C16 N17 C18 0.0(2) . . . . ?
C15 C16 N17 C18 -179.14(14) . . . . ?
C21 C16 N17 Cu -179.10(12) . . . . ?
C15 C16 N17 Cu 1.82(17) . . . . ?
C16 N17 C18 C19 -0.8(2) . . . . ?
Cu N17 C18 C19 178.03(12) . . . . ?
N17 C18 C19 C20 0.7(2) . . . . ?
N17 C18 C19 C22 -177.76(15) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C22 C19 C20 C21 178.80(16) . . . . ?
C19 C20 C21 C16 -1.2(3) . . . . ?
N17 C16 C21 C20 1.1(2) . . . . ?
C15 C16 C21 C20 -179.93(16) . . . . ?
C20 C19 C22 N23 -118.10(18) . . . . ?
C18 C19 C22 N23 60.3(2) . . . . ?
C19 C22 N23 C24 177.40(14) . . . . ?
C19 C22 N23 C28 57.93(19) . . . . ?
C22 N23 C24 C25 -178.45(14) . . . . ?
C28 N23 C24 C25 -57.10(18) . . . . ?
N23 C24 C25 O26 57.0(2) . . . . ?
C24 C25 O26 C27 -56.9(2) . . . . ?
C25 O26 C27 C28 58.76(19) . . . . ?
C24 N23 C28 C27 58.82(18) . . . . ?
C22 N23 C28 C27 178.27(14) . . . . ?
O26 C27 C28 N23 -60.48(19) . . . . ?
