#------------------------------------------------------------------------------
#$Date: 2023-07-05 02:03:06 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/33/7713371.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_7713371
loop_
_publ_author_name
'Arion, Vladimir'
'Wittmann, Christopher'
'Dömötör, Orsolya'
'Kuznetcova, Irina'
'Spengler, Gabriella'
'Reynisson, Johannes'
'Holder, Lauren'
'Miller, Gavin John'
'Enyedy, Eva A.'
'Bai, Ruoli'
'Hamel, Ernest'
_publ_section_title
;
 Indolo[2,3-e]benzazocines and indolo[2,3-f]benzazonines and their
 copper(II) complexes as microtubule destabilizing agents
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01632C
_journal_year                    2023
_chemical_formula_moiety         'C24 H21 Cl2 Cu N5, 2(C3 H7 N O)'
_chemical_formula_sum            'C30 H35 Cl2 Cu N7 O2'
_chemical_formula_weight         660.09
_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   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                77.4544(10)
_cell_angle_beta                 76.6520(12)
_cell_angle_gamma                85.2866(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8729(2)
_cell_length_b                   9.9230(2)
_cell_length_c                   16.4367(4)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      29.709
_cell_measurement_theta_min      2.602
_cell_volume                     1528.50(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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      140(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_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  0.0704
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37246
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.087
_diffrn_reflns_theta_min         2.104
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.5642
_exptl_absorpt_correction_T_min  0.4875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             686
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         8880
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0296P)²+0.7176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6201
_reflns_number_total             8880
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01632c2.cif
_cod_data_source_block           chwi665
_cod_database_code               7713371
_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   0.703
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2014-3
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
Cu Cu 0.32205(2) 0.17244(2) 0.53583(2) 0.01658(7) Uani 1 1 d . . . . .
Cl1 Cl 0.13704(5) 0.03901(5) 0.57783(3) 0.02514(12) Uani 1 1 d . . . . .
Cl2 Cl 0.25736(5) 0.35001(5) 0.62597(3) 0.02171(11) Uani 1 1 d . . . . .
C1 C 0.2983(2) 0.3665(2) 0.13852(13) 0.0233(4) Uani 1 1 d . . . . .
H1 H 0.3834 0.3932 0.0995 0.028 Uiso 1 1 calc R U . . .
C2 C 0.2125(2) 0.2810(2) 0.11912(14) 0.0273(5) Uani 1 1 d . . . . .
H2 H 0.2388 0.2490 0.0670 0.033 Uiso 1 1 calc R U . . .
C3 C 0.0876(2) 0.2416(2) 0.17564(15) 0.0303(5) Uani 1 1 d . . . . .
H3 H 0.0281 0.1828 0.1624 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0507(2) 0.2884(2) 0.25120(14) 0.0265(5) Uani 1 1 d . . . . .
H4 H -0.0340 0.2597 0.2901 0.032 Uiso 1 1 calc R U . . .
C4A C 0.1340(2) 0.3765(2) 0.27182(13) 0.0211(4) Uani 1 1 d . . . . .
C5 C 0.0877(2) 0.4296(2) 0.35379(13) 0.0232(4) Uani 1 1 d . . . . .
H5A H -0.0148 0.4443 0.3658 0.028 Uiso 1 1 calc R U . . .
H5B H 0.1296 0.5200 0.3460 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1283(2) 0.3316(2) 0.43038(13) 0.0238(5) Uani 1 1 d . . . . .
H6A H 0.0815 0.3668 0.4821 0.029 Uiso 1 1 calc R U . . .
H6B H 0.0888 0.2409 0.4354 0.029 Uiso 1 1 calc R U . . .
N7 N 0.27561(17) 0.30729(17) 0.43261(10) 0.0183(3) Uani 1 1 d . . . . .
C8 C 0.3796(2) 0.3809(2) 0.38800(12) 0.0170(4) Uani 1 1 d . . . . .
C8A C 0.3924(2) 0.49515(19) 0.31173(12) 0.0171(4) Uani 1 1 d . . . . .
N9 N 0.47933(17) 0.60154(16) 0.30535(10) 0.0190(3) Uani 1 1 d D . . . .
H9 H 0.5160 0.6162 0.3465 0.023 Uiso 1 1 calc DR U . . .
C9A C 0.4986(2) 0.6802(2) 0.22399(12) 0.0187(4) Uani 1 1 d . . . . .
C10 C 0.5776(2) 0.7978(2) 0.18813(14) 0.0240(4) Uani 1 1 d . . . . .
H10 H 0.6283 0.8350 0.2203 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5785(2) 0.8576(2) 0.10378(14) 0.0285(5) Uani 1 1 d . . . . .
H11 H 0.6318 0.9371 0.0771 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5022(2) 0.8033(2) 0.05675(14) 0.0282(5) Uani 1 1 d . . . . .
H12 H 0.5049 0.8472 -0.0010 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4235(2) 0.6880(2) 0.09223(13) 0.0237(4) Uani 1 1 d . . . . .
H13 H 0.3713 0.6530 0.0600 0.028 Uiso 1 1 calc R U . . .
C13A C 0.4226(2) 0.6233(2) 0.17799(12) 0.0189(4) Uani 1 1 d . . . . .
C13B C 0.3538(2) 0.5049(2) 0.23493(12) 0.0178(4) Uani 1 1 d . . . . .
C13C C 0.2615(2) 0.4147(2) 0.21515(12) 0.0190(4) Uani 1 1 d . . . . .
N14 N 0.50626(17) 0.35541(16) 0.41208(10) 0.0175(3) Uani 1 1 d D . . . .
H14 H 0.5808 0.4029 0.3853 0.021 Uiso 1 1 calc DR U . . .
N15 N 0.50485(17) 0.24971(16) 0.48131(10) 0.0171(3) Uani 1 1 d . . . . .
C16 C 0.6104(2) 0.2136(2) 0.51456(12) 0.0177(4) Uani 1 1 d . . . . .
C17 C 0.5811(2) 0.09591(19) 0.58846(12) 0.0177(4) Uani 1 1 d . . . . .
N18 N 0.44819(17) 0.05188(16) 0.60836(10) 0.0170(3) Uani 1 1 d . . . . .
C19 C 0.4121(2) -0.0539(2) 0.67407(13) 0.0210(4) Uani 1 1 d . . . . .
H19 H 0.3200 -0.0860 0.6874 0.025 Uiso 1 1 calc R U . . .
C20 C 0.5047(2) -0.1182(2) 0.72333(13) 0.0249(5) Uani 1 1 d . . . . .
H20 H 0.4759 -0.1924 0.7702 0.030 Uiso 1 1 calc R U . . .
C21 C 0.6391(2) -0.0732(2) 0.70356(14) 0.0258(5) Uani 1 1 d . . . . .
H21 H 0.7040 -0.1158 0.7367 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6786(2) 0.0353(2) 0.63448(13) 0.0223(4) Uani 1 1 d . . . . .
H22 H 0.7710 0.0671 0.6192 0.027 Uiso 1 1 calc R U . . .
C23 C 0.7474(2) 0.2807(2) 0.48620(14) 0.0249(5) Uani 1 1 d . . . . .
H23A H 0.8149 0.2232 0.4537 0.037 Uiso 1 1 calc R U . . .
H23B H 0.7803 0.2913 0.5363 0.037 Uiso 1 1 calc R U . . .
H23C H 0.7373 0.3717 0.4499 0.037 Uiso 1 1 calc R U . . .
O1 O 1.15590(18) -0.02836(17) 0.86303(11) 0.0378(4) Uani 1 1 d . . . . .
C24 C 1.0998(2) 0.0552(2) 0.81350(15) 0.0287(5) Uani 1 1 d . . . . .
H24 H 1.1531 0.0855 0.7573 0.034 Uiso 1 1 calc R U . . .
N24 N 0.9702(2) 0.10733(19) 0.83174(12) 0.0291(4) Uani 1 1 d . . . . .
C25 C 0.9118(3) 0.2038(3) 0.76768(16) 0.0403(6) Uani 1 1 d . . . . .
H25A H 0.8285 0.1653 0.7599 0.061 Uiso 1 1 calc R U . . .
H25B H 0.9809 0.2197 0.7134 0.061 Uiso 1 1 calc R U . . .
H25C H 0.8867 0.2915 0.7865 0.061 Uiso 1 1 calc R U . . .
C26 C 0.8810(3) 0.0682(3) 0.91636(16) 0.0423(7) Uani 1 1 d . . . . .
H26A H 0.8678 0.1466 0.9451 0.063 Uiso 1 1 calc R U . . .
H26B H 0.9246 -0.0101 0.9498 0.063 Uiso 1 1 calc R U . . .
H26C H 0.7904 0.0417 0.9111 0.063 Uiso 1 1 calc R U . . .
O2 O 0.29909(16) 0.63962(16) 0.73525(9) 0.0279(4) Uani 1 1 d . . . . .
C27 C 0.2257(2) 0.5424(2) 0.77712(13) 0.0233(4) Uani 1 1 d . . . . .
H27 H 0.1938 0.4847 0.7467 0.028 Uiso 1 1 calc R U . . .
N27 N 0.18862(19) 0.51326(19) 0.86149(11) 0.0252(4) Uani 1 1 d . . . . .
C28 C 0.2368(3) 0.5959(3) 0.91127(16) 0.0493(8) Uani 1 1 d . . . . .
H28A H 0.3361 0.6129 0.8882 0.074 Uiso 1 1 calc R U . . .
H28B H 0.2229 0.5464 0.9709 0.074 Uiso 1 1 calc R U . . .
H28C H 0.1841 0.6843 0.9083 0.074 Uiso 1 1 calc R U . . .
C29 C 0.0944(3) 0.4018(3) 0.90409(17) 0.0458(7) Uani 1 1 d . . . . .
H29A H 0.0036 0.4405 0.9289 0.069 Uiso 1 1 calc R U . . .
H29B H 0.1329 0.3413 0.9495 0.069 Uiso 1 1 calc R U . . .
H29C H 0.0831 0.3484 0.8626 0.069 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'
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
N15 Cu N7 79.40(7) . . ?
N15 Cu N18 78.04(7) . . ?
N7 Cu N18 156.45(6) . . ?
N15 Cu Cl1 164.17(5) . . ?
N7 Cu Cl1 101.74(5) . . ?
N18 Cu Cl1 98.15(5) . . ?
N15 Cu Cl2 93.00(5) . . ?
N7 Cu Cl2 91.41(5) . . ?
N18 Cu Cl2 96.42(5) . . ?
Cl1 Cu Cl2 102.73(2) . . ?
C2 C1 C13C 120.89(19) . . ?
C2 C1 H1 119.6 . . ?
C13C C1 H1 119.6 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C4A 121.8(2) . . ?
C3 C4 H4 119.1 . . ?
C4A C4 H4 119.1 . . ?
C4 C4A C13C 118.71(19) . . ?
C4 C4A C5 120.24(18) . . ?
C13C C4A C5 121.05(19) . . ?
C4A C5 C6 113.14(17) . . ?
C4A C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C4A C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N7 C6 C5 119.29(16) . . ?
N7 C6 H6A 107.5 . . ?
C5 C6 H6A 107.5 . . ?
N7 C6 H6B 107.5 . . ?
C5 C6 H6B 107.5 . . ?
H6A C6 H6B 107.0 . . ?
C8 N7 C6 128.04(17) . . ?
C8 N7 Cu 113.03(14) . . ?
C6 N7 Cu 117.09(12) . . ?
N7 C8 N14 118.30(17) . . ?
N7 C8 C8A 131.96(19) . . ?
N14 C8 C8A 109.74(16) . . ?
C13B C8A N9 109.86(16) . . ?
C13B C8A C8 130.95(18) . . ?
N9 C8A C8 117.90(18) . . ?
C9A N9 C8A 108.52(17) . . ?
C9A N9 H9 125.7 . . ?
C8A N9 H9 125.7 . . ?
N9 C9A C10 129.0(2) . . ?
N9 C9A C13A 108.28(17) . . ?
C10 C9A C13A 122.69(19) . . ?
C11 C10 C9A 117.0(2) . . ?
C11 C10 H10 121.5 . . ?
C9A C10 H10 121.5 . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 121.7(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C13A 118.2(2) . . ?
C12 C13 H13 120.9 . . ?
C13A C13 H13 120.9 . . ?
C9A C13A C13 119.10(18) . . ?
C9A C13A C13B 107.37(17) . . ?
C13 C13A C13B 133.5(2) . . ?
C8A C13B C13A 105.97(18) . . ?
C8A C13B C13C 127.31(17) . . ?
C13A C13B C13C 126.72(18) . . ?
C1 C13C C4A 119.10(19) . . ?
C1 C13C C13B 120.24(17) . . ?
C4A C13C C13B 120.65(18) . . ?
N15 N14 C8 113.81(15) . . ?
N15 N14 H14 123.1 . . ?
C8 N14 H14 123.1 . . ?
C16 N15 N14 123.07(17) . . ?
C16 N15 Cu 121.39(13) . . ?
N14 N15 Cu 115.08(13) . . ?
N15 C16 C17 112.11(17) . . ?
N15 C16 C23 125.66(18) . . ?
C17 C16 C23 122.21(18) . . ?
N18 C17 C22 121.92(18) . . ?
N18 C17 C16 114.42(17) . . ?
C22 C17 C16 123.66(18) . . ?
C19 N18 C17 118.71(18) . . ?
C19 N18 Cu 127.89(14) . . ?
C17 N18 Cu 113.20(13) . . ?
N18 C19 C20 122.2(2) . . ?
N18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 119.18(19) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 119.2(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C21 118.8(2) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 N24 125.5(2) . . ?
O1 C24 H24 117.2 . . ?
N24 C24 H24 117.2 . . ?
C24 N24 C25 121.35(19) . . ?
C24 N24 C26 121.2(2) . . ?
C25 N24 C26 117.42(19) . . ?
N24 C25 H25A 109.5 . . ?
N24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N24 C26 H26A 109.5 . . ?
N24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O2 C27 N27 124.3(2) . . ?
O2 C27 H27 117.9 . . ?
N27 C27 H27 117.9 . . ?
C27 N27 C28 120.24(19) . . ?
C27 N27 C29 119.7(2) . . ?
C28 N27 C29 119.99(19) . . ?
N27 C28 H28A 109.5 . . ?
N27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N27 C29 H29A 109.5 . . ?
N27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N27 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
Cu N15 1.9571(16) . ?
Cu N7 2.0375(17) . ?
Cu N18 2.0554(17) . ?
Cu Cl1 2.2325(5) . ?
Cu Cl2 2.4940(5) . ?
C1 C2 1.378(3) . ?
C1 C13C 1.403(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.390(3) . ?
C4 H4 0.9500 . ?
C4A C13C 1.407(3) . ?
C4A C5 1.512(3) . ?
C5 C6 1.526(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.462(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C8 1.291(2) . ?
C8 N14 1.385(3) . ?
C8 C8A 1.485(3) . ?
C8A C13B 1.382(3) . ?
C8A N9 1.386(3) . ?
N9 C9A 1.374(2) . ?
N9 H9 0.8800 . ?
C9A C10 1.399(3) . ?
C9A C13A 1.404(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 C13A 1.415(3) . ?
C13 H13 0.9500 . ?
C13A C13B 1.441(3) . ?
C13B C13C 1.461(3) . ?
N14 N15 1.368(2) . ?
N14 H14 0.8800 . ?
N15 C16 1.277(3) . ?
C16 C17 1.483(3) . ?
C16 C23 1.488(3) . ?
C17 N18 1.362(3) . ?
C17 C22 1.379(3) . ?
N18 C19 1.336(2) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1 C24 1.223(3) . ?
C24 N24 1.333(3) . ?
C24 H24 0.9500 . ?
N24 C25 1.452(3) . ?
N24 C26 1.455(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O2 C27 1.235(3) . ?
C27 N27 1.323(3) . ?
C27 H27 0.9500 . ?
N27 C28 1.451(3) . ?
N27 C29 1.453(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
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
C6 H6B Cl1 0.99 2.84 3.363(2) 114.0 .
N9 H9 Cl2 0.88 2.45 3.1718(18) 140.2 2_666
N14 H14 Cl2 0.88 2.99 3.7463(17) 145.9 2_666
N14 H14 O2 0.88 2.17 2.716(2) 119.7 2_666
C19 H19 Cl1 0.95 2.87 3.416(2) 118.0 .
C23 H23A Cl1 0.98 2.74 3.574(2) 142.7 2_656
C23 H23C Cl2 0.98 2.77 3.729(2) 165.8 2_666
C27 H27 Cl2 0.95 2.56 3.394(2) 146.4 .
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
C13C C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C4A 1.2(3) . . . . ?
C3 C4 C4A C13C -2.2(3) . . . . ?
C3 C4 C4A C5 177.91(19) . . . . ?
C4 C4A C5 C6 86.2(2) . . . . ?
C13C C4A C5 C6 -93.7(2) . . . . ?
C4A C5 C6 N7 66.3(3) . . . . ?
C5 C6 N7 C8 17.7(3) . . . . ?
C5 C6 N7 Cu -178.89(15) . . . . ?
C6 N7 C8 N14 167.08(18) . . . . ?
Cu N7 C8 N14 3.2(2) . . . . ?
C6 N7 C8 C8A -12.4(4) . . . . ?
Cu N7 C8 C8A -176.28(17) . . . . ?
N7 C8 C8A C13B -50.2(3) . . . . ?
N14 C8 C8A C13B 130.3(2) . . . . ?
N7 C8 C8A N9 144.2(2) . . . . ?
N14 C8 C8A N9 -35.2(2) . . . . ?
C13B C8A N9 C9A -0.5(2) . . . . ?
C8 C8A N9 C9A 167.91(16) . . . . ?
C8A N9 C9A C10 179.9(2) . . . . ?
C8A N9 C9A C13A 0.1(2) . . . . ?
N9 C9A C10 C11 -179.80(19) . . . . ?
C13A C9A C10 C11 -0.1(3) . . . . ?
C9A C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C13A -0.9(3) . . . . ?
N9 C9A C13A C13 178.78(17) . . . . ?
C10 C9A C13A C13 -1.0(3) . . . . ?
N9 C9A C13A C13B 0.3(2) . . . . ?
C10 C9A C13A C13B -179.48(18) . . . . ?
C12 C13 C13A C9A 1.4(3) . . . . ?
C12 C13 C13A C13B 179.4(2) . . . . ?
N9 C8A C13B C13A 0.7(2) . . . . ?
C8 C8A C13B C13A -165.73(19) . . . . ?
N9 C8A C13B C13C -178.96(18) . . . . ?
C8 C8A C13B C13C 14.6(3) . . . . ?
C9A C13A C13B C8A -0.6(2) . . . . ?
C13 C13A C13B C8A -178.8(2) . . . . ?
C9A C13A C13B C13C 179.05(18) . . . . ?
C13 C13A C13B C13C 0.9(4) . . . . ?
C2 C1 C13C C4A -1.1(3) . . . . ?
C2 C1 C13C C13B 179.80(19) . . . . ?
C4 C4A C13C C1 2.1(3) . . . . ?
C5 C4A C13C C1 -178.01(18) . . . . ?
C4 C4A C13C C13B -178.81(19) . . . . ?
C5 C4A C13C C13B 1.1(3) . . . . ?
C8A C13B C13C C1 -134.9(2) . . . . ?
C13A C13B C13C C1 45.5(3) . . . . ?
C8A C13B C13C C4A 46.0(3) . . . . ?
C13A C13B C13C C4A -133.6(2) . . . . ?
N7 C8 N14 N15 1.4(3) . . . . ?
C8A C8 N14 N15 -179.00(15) . . . . ?
C8 N14 N15 C16 -177.86(18) . . . . ?
C8 N14 N15 Cu -5.6(2) . . . . ?
N14 N15 C16 C17 -179.69(15) . . . . ?
Cu N15 C16 C17 8.5(2) . . . . ?
N14 N15 C16 C23 1.8(3) . . . . ?
Cu N15 C16 C23 -169.98(15) . . . . ?
N15 C16 C17 N18 -1.9(2) . . . . ?
C23 C16 C17 N18 176.66(18) . . . . ?
N15 C16 C17 C22 178.58(19) . . . . ?
C23 C16 C17 C22 -2.9(3) . . . . ?
C22 C17 N18 C19 -0.5(3) . . . . ?
C16 C17 N18 C19 179.94(16) . . . . ?
C22 C17 N18 Cu 174.79(15) . . . . ?
C16 C17 N18 Cu -4.8(2) . . . . ?
C17 N18 C19 C20 1.2(3) . . . . ?
Cu N18 C19 C20 -173.34(15) . . . . ?
N18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
N18 C17 C22 C21 -0.5(3) . . . . ?
C16 C17 C22 C21 179.00(18) . . . . ?
C20 C21 C22 C17 0.9(3) . . . . ?
O1 C24 N24 C25 -178.5(2) . . . . ?
O1 C24 N24 C26 0.6(4) . . . . ?
O2 C27 N27 C28 -1.4(3) . . . . ?
O2 C27 N27 C29 176.0(2) . . . . ?
