#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:55:43 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179218 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/44/4314479.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_4314479
loop_
_publ_author_name
'Michael F. Primik'
'Gerhard Mühlgassner'
'Michael A. Jakupec'
'Olivier Zava'
'Paul J. Dyson'
'Vladimir B. Arion'
'Bernhard K. Keppler'
_publ_section_title
;
 Highly Cytotoxic Copper(II) Complexes with Modified Paullone Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              302
_journal_page_last               311
_journal_paper_doi               10.1021/ic902042a
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         '4(C22 H17.5 Br Cl2 Cu N5), O3'
_chemical_formula_sum            'C88 H70 Br4 Cl8 Cu4 N20 O3'
_chemical_formula_weight         2313.04
_chemical_name_systematic
; 
N-(9-Bromo-7,12-dihydroindolo-[3,2-d][1]benzazepin-6-yliden)-N'-
(1-pyridin-2-yl-methyliden)-azin-5-ide-dichlorido-copper(II)
methanol solvate  
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.691(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            1
_cell_length_a                   12.7662(8)
_cell_length_b                   13.5586(8)
_cell_length_c                   13.1869(8)
_cell_measurement_reflns_used    1447
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.70
_cell_measurement_theta_min      2.98
_cell_volume                     2197.5(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            64787
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    3.080
_exptl_absorpt_correction_T_max  0.8133
_exptl_absorpt_correction_T_min  0.7481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1154
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.094
_refine_diff_density_min         -1.288
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5517
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0362P)²+3.7430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                4029
_reflns_number_total             5517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic902042a_si_002_4.cif
_cod_data_source_block           mipr039
_cod_database_code               4314479
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.75282(3) 0.42772(3) 0.94415(3) 0.02756(11) Uani 1 1 d . . .
Cu Cu 0.62414(3) 1.08613(3) 0.86133(3) 0.00939(9) Uani 1 1 d . . .
Cl1 Cl 0.75431(6) 1.16257(6) 0.98479(6) 0.01656(17) Uani 1 1 d . . .
Cl2 Cl 0.55468(7) 1.20598(6) 0.72233(7) 0.02166(19) Uani 1 1 d . . .
N5 N 0.7179(2) 1.00072(19) 0.7934(2) 0.0108(5) Uani 1 1 d . . .
N12 N 0.9723(2) 0.82041(19) 0.9563(2) 0.0127(5) Uani 1 1 d . . .
H12 H 1.0314 0.8468 0.9979 0.015 Uiso 1 1 calc R . .
N13 N 0.5713(2) 0.89769(19) 0.76732(19) 0.0108(5) Uani 1 1 d . . .
H13 H 0.5350 0.8440 0.7416 0.013 Uiso 1 1 calc R . .
N14 N 0.5290(2) 0.96991(18) 0.81515(19) 0.0104(5) Uani 1 1 d . . .
N17 N 0.4946(2) 1.11630(19) 0.92174(19) 0.0110(5) Uani 1 1 d . . .
C1 C 1.0202(3) 1.0008(2) 0.8322(2) 0.0145(7) Uani 1 1 d . . .
H1 H 1.0829 0.9619 0.8619 0.017 Uiso 1 1 calc R . .
C2 C 1.0318(3) 1.0918(2) 0.7902(2) 0.0166(7) Uani 1 1 d . . .
H2 H 1.1022 1.1148 0.7908 0.020 Uiso 1 1 calc R . .
C3 C 0.9411(3) 1.1503(2) 0.7467(3) 0.0165(7) Uani 1 1 d . . .
H3 H 0.9494 1.2123 0.7161 0.020 Uiso 1 1 calc R . .
C4 C 0.8391(3) 1.1178(2) 0.7484(2) 0.0158(7) Uani 1 1 d . . .
H4 H 0.7775 1.1588 0.7211 0.019 Uiso 1 1 calc R . .
C4A C 0.8254(2) 1.0250(2) 0.7899(2) 0.0110(6) Uani 1 1 d . . .
C6 C 0.6751(2) 0.9154(2) 0.7625(2) 0.0109(6) Uani 1 1 d . . .
C7 C 0.7321(2) 0.8309(2) 0.7284(2) 0.0125(6) Uani 1 1 d . . .
H7A H 0.7628 0.8509 0.6702 0.015 Uiso 1 1 calc R . .
H7B H 0.6811 0.7754 0.7041 0.015 Uiso 1 1 calc R . .
C7A C 0.8212(2) 0.8013(2) 0.8235(2) 0.0106(6) Uani 1 1 d . . .
C7B C 0.8370(2) 0.7135(2) 0.8849(2) 0.0114(6) Uani 1 1 d . . .
C8 C 0.7797(3) 0.6240(2) 0.8785(2) 0.0137(6) Uani 1 1 d . . .
H8 H 0.7152 0.6125 0.8238 0.016 Uiso 1 1 calc R . .
C9 C 0.8203(3) 0.5538(2) 0.9544(3) 0.0171(7) Uani 1 1 d . . .
C10 C 0.9134(3) 0.5698(2) 1.0382(3) 0.0187(7) Uani 1 1 d . . .
H10 H 0.9371 0.5203 1.0904 0.022 Uiso 1 1 calc R . .
C11 C 0.9710(3) 0.6569(2) 1.0454(3) 0.0166(7) Uani 1 1 d . . .
H11 H 1.0346 0.6681 1.1014 0.020 Uiso 1 1 calc R . .
C11A C 0.9329(3) 0.7278(2) 0.9678(2) 0.0131(6) Uani 1 1 d . . .
C12A C 0.9039(2) 0.8654(2) 0.8687(2) 0.0113(6) Uani 1 1 d . . .
C12B C 0.9170(3) 0.9646(2) 0.8318(2) 0.0124(6) Uani 1 1 d . . .
C15 C 0.4365(2) 0.9643(2) 0.8347(2) 0.0116(6) Uani 1 1 d . . .
H15 H 0.3882 0.9102 0.8139 0.014 Uiso 1 1 calc R . .
C16 C 0.4123(2) 1.0498(2) 0.8926(2) 0.0105(6) Uani 1 1 d . . .
C18 C 0.4788(3) 1.1958(2) 0.9753(2) 0.0142(7) Uani 1 1 d . . .
H18 H 0.5362 1.2423 0.9967 0.017 Uiso 1 1 calc R . .
C19 C 0.3816(3) 1.2134(2) 1.0011(2) 0.0152(7) Uani 1 1 d . . .
H19 H 0.3727 1.2713 1.0386 0.018 Uiso 1 1 calc R . .
C20 C 0.2989(3) 1.1457(3) 0.9716(2) 0.0168(7) Uani 1 1 d . . .
H20 H 0.2318 1.1562 0.9882 0.020 Uiso 1 1 calc R . .
C21 C 0.3146(3) 1.0617(2) 0.9170(2) 0.0147(7) Uani 1 1 d . . .
H21 H 0.2590 1.0134 0.8968 0.018 Uiso 1 1 calc R . .
O1 O 0.4726(6) 0.4304(5) 0.9979(5) 0.0477(17) Uani 0.50 1 d P . .
O2 O 0.5000 0.5000 1.0000 0.082(4) Uani 0.50 2 d SPU . .
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'
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'
Br Br -0.2901 2.4595 '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
N14 Cu N5 78.28(10) . . ?
N14 Cu N17 77.75(10) . . ?
N5 Cu N17 155.53(10) . . ?
N14 Cu Cl1 149.67(8) . . ?
N5 Cu Cl1 100.01(7) . . ?
N17 Cu Cl1 98.18(7) . . ?
N14 Cu Cl2 103.39(7) . . ?
N5 Cu Cl2 100.75(7) . . ?
N17 Cu Cl2 89.52(7) . . ?
Cl1 Cu Cl2 106.63(3) . . ?
C6 N5 C4A 121.5(3) . . ?
C6 N5 Cu 113.5(2) . . ?
C4A N5 Cu 124.6(2) . . ?
C11A N12 C12A 109.1(3) . . ?
C11A N12 H12 125.5 . . ?
C12A N12 H12 125.5 . . ?
N14 N13 C6 114.1(2) . . ?
N14 N13 H13 123.0 . . ?
C6 N13 H13 123.0 . . ?
C15 N14 N13 123.9(3) . . ?
C15 N14 Cu 120.5(2) . . ?
N13 N14 Cu 115.50(19) . . ?
C18 N17 C16 118.0(3) . . ?
C18 N17 Cu 128.1(2) . . ?
C16 N17 Cu 113.5(2) . . ?
C2 C1 C12B 120.9(3) . . ?
C2 C1 H1 119.5 . . ?
C12B C1 H1 119.5 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C4A 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C4A C4 H4 119.7 . . ?
C4 C4A C12B 119.7(3) . . ?
C4 C4A N5 116.3(3) . . ?
C12B C4A N5 123.8(3) . . ?
N5 C6 N13 118.3(3) . . ?
N5 C6 C7 125.7(3) . . ?
N13 C6 C7 116.0(3) . . ?
C6 C7 C7A 106.0(2) . . ?
C6 C7 H7A 110.5 . . ?
C7A C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
C7A C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C12A C7A C7B 108.0(3) . . ?
C12A C7A C7 120.9(3) . . ?
C7B C7A C7 131.1(3) . . ?
C8 C7B C11A 119.4(3) . . ?
C8 C7B C7A 134.1(3) . . ?
C11A C7B C7A 106.5(3) . . ?
C9 C8 C7B 117.7(3) . . ?
C9 C8 H8 121.1 . . ?
C7B C8 H8 121.1 . . ?
C8 C9 C10 122.5(3) . . ?
C8 C9 Br 119.7(2) . . ?
C10 C9 Br 117.8(2) . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C11A 117.8(3) . . ?
C10 C11 H11 121.1 . . ?
C11A C11 H11 121.1 . . ?
N12 C11A C11 130.2(3) . . ?
N12 C11A C7B 107.7(3) . . ?
C11 C11A C7B 122.0(3) . . ?
C7A C12A N12 108.6(3) . . ?
C7A C12A C12B 125.8(3) . . ?
N12 C12A C12B 125.6(3) . . ?
C1 C12B C4A 118.4(3) . . ?
C1 C12B C12A 120.9(3) . . ?
C4A C12B C12A 120.6(3) . . ?
N14 C15 C16 113.3(3) . . ?
N14 C15 H15 123.4 . . ?
C16 C15 H15 123.4 . . ?
N17 C16 C21 122.4(3) . . ?
N17 C16 C15 114.6(3) . . ?
C21 C16 C15 123.0(3) . . ?
N17 C18 C19 122.7(3) . . ?
N17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 119.1(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C20 118.9(3) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
O1 O2 O1 180.0(7) 3_667 . ?
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 C9 1.902(3) . ?
Cu N14 1.982(3) . ?
Cu N5 2.038(3) . ?
Cu N17 2.062(3) . ?
Cu Cl1 2.2411(8) . ?
Cu Cl2 2.4306(8) . ?
N5 C6 1.296(4) . ?
N5 C4A 1.425(4) . ?
N12 C11A 1.376(4) . ?
N12 C12A 1.388(4) . ?
N12 H12 0.8800 . ?
N13 N14 1.353(3) . ?
N13 C6 1.366(4) . ?
N13 H13 0.8800 . ?
N14 C15 1.278(4) . ?
N17 C18 1.333(4) . ?
N17 C16 1.359(4) . ?
C1 C2 1.377(5) . ?
C1 C12B 1.404(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.402(4) . ?
C4 H4 0.9500 . ?
C4A C12B 1.412(4) . ?
C6 C7 1.490(4) . ?
C7 C7A 1.501(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7A C12A 1.373(4) . ?
C7A C7B 1.423(4) . ?
C7B C8 1.408(4) . ?
C7B C11A 1.417(4) . ?
C8 C9 1.378(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(5) . ?
C10 C11 1.381(5) . ?
C10 H10 0.9500 . ?
C11 C11A 1.392(4) . ?
C11 H11 0.9500 . ?
C12A C12B 1.455(4) . ?
C15 C16 1.466(4) . ?
C15 H15 0.9500 . ?
C16 C21 1.379(4) . ?
C18 C19 1.393(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O1 O2 1.004(7) . ?
O2 O1 1.004(7) 3_667 ?
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
N14 Cu N5 C6 -4.4(2) . . . . ?
N17 Cu N5 C6 7.3(4) . . . . ?
Cl1 Cu N5 C6 144.8(2) . . . . ?
Cl2 Cu N5 C6 -106.0(2) . . . . ?
N14 Cu N5 C4A -177.4(2) . . . . ?
N17 Cu N5 C4A -165.7(2) . . . . ?
Cl1 Cu N5 C4A -28.3(2) . . . . ?
Cl2 Cu N5 C4A 81.0(2) . . . . ?
C6 N13 N14 C15 -174.5(3) . . . . ?
C6 N13 N14 Cu 2.5(3) . . . . ?
N5 Cu N14 C15 178.1(3) . . . . ?
N17 Cu N14 C15 3.0(2) . . . . ?
Cl1 Cu N14 C15 88.2(3) . . . . ?
Cl2 Cu N14 C15 -83.5(2) . . . . ?
N5 Cu N14 N13 0.94(19) . . . . ?
N17 Cu N14 N13 -174.1(2) . . . . ?
Cl1 Cu N14 N13 -88.9(2) . . . . ?
Cl2 Cu N14 N13 99.35(19) . . . . ?
N14 Cu N17 C18 -178.2(3) . . . . ?
N5 Cu N17 C18 170.1(2) . . . . ?
Cl1 Cu N17 C18 32.4(3) . . . . ?
Cl2 Cu N17 C18 -74.3(2) . . . . ?
N14 Cu N17 C16 -5.2(2) . . . . ?
N5 Cu N17 C16 -17.0(4) . . . . ?
Cl1 Cu N17 C16 -154.67(19) . . . . ?
Cl2 Cu N17 C16 98.59(19) . . . . ?
C12B C1 C2 C3 0.4(5) . . . . ?
C1 C2 C3 C4 1.7(5) . . . . ?
C2 C3 C4 C4A -2.3(5) . . . . ?
C3 C4 C4A C12B 0.9(5) . . . . ?
C3 C4 C4A N5 176.5(3) . . . . ?
C6 N5 C4A C4 134.2(3) . . . . ?
Cu N5 C4A C4 -53.3(3) . . . . ?
C6 N5 C4A C12B -50.4(4) . . . . ?
Cu N5 C4A C12B 122.2(3) . . . . ?
C4A N5 C6 N13 -179.4(3) . . . . ?
Cu N5 C6 N13 7.3(3) . . . . ?
C4A N5 C6 C7 5.1(5) . . . . ?
Cu N5 C6 C7 -168.2(2) . . . . ?
N14 N13 C6 N5 -6.6(4) . . . . ?
N14 N13 C6 C7 169.4(2) . . . . ?
N5 C6 C7 C7A 63.9(4) . . . . ?
N13 C6 C7 C7A -111.7(3) . . . . ?
C6 C7 C7A C12A -62.7(4) . . . . ?
C6 C7 C7A C7B 114.1(4) . . . . ?
C12A C7A C7B C8 179.3(3) . . . . ?
C7 C7A C7B C8 2.2(6) . . . . ?
C12A C7A C7B C11A -0.5(3) . . . . ?
C7 C7A C7B C11A -177.7(3) . . . . ?
C11A C7B C8 C9 0.0(5) . . . . ?
C7A C7B C8 C9 -179.8(3) . . . . ?
C7B C8 C9 C10 2.1(5) . . . . ?
C7B C8 C9 Br -175.3(2) . . . . ?
C8 C9 C10 C11 -2.5(5) . . . . ?
Br C9 C10 C11 174.9(3) . . . . ?
C9 C10 C11 C11A 0.6(5) . . . . ?
C12A N12 C11A C11 -177.4(3) . . . . ?
C12A N12 C11A C7B 0.2(3) . . . . ?
C10 C11 C11A N12 178.8(3) . . . . ?
C10 C11 C11A C7B 1.4(5) . . . . ?
C8 C7B C11A N12 -179.7(3) . . . . ?
C7A C7B C11A N12 0.2(3) . . . . ?
C8 C7B C11A C11 -1.8(5) . . . . ?
C7A C7B C11A C11 178.1(3) . . . . ?
C7B C7A C12A N12 0.6(3) . . . . ?
C7 C7A C12A N12 178.1(3) . . . . ?
C7B C7A C12A C12B -178.6(3) . . . . ?
C7 C7A C12A C12B -1.1(5) . . . . ?
C11A N12 C12A C7A -0.5(3) . . . . ?
C11A N12 C12A C12B 178.7(3) . . . . ?
C2 C1 C12B C4A -1.8(5) . . . . ?
C2 C1 C12B C12A 175.2(3) . . . . ?
C4 C4A C12B C1 1.1(4) . . . . ?
N5 C4A C12B C1 -174.2(3) . . . . ?
C4 C4A C12B C12A -175.8(3) . . . . ?
N5 C4A C12B C12A 8.9(5) . . . . ?
C7A C12A C12B C1 -139.9(3) . . . . ?
N12 C12A C12B C1 40.9(5) . . . . ?
C7A C12A C12B C4A 36.9(5) . . . . ?
N12 C12A C12B C4A -142.2(3) . . . . ?
N13 N14 C15 C16 176.6(2) . . . . ?
Cu N14 C15 C16 -0.3(3) . . . . ?
C18 N17 C16 C21 -0.4(4) . . . . ?
Cu N17 C16 C21 -174.1(2) . . . . ?
C18 N17 C16 C15 -179.6(3) . . . . ?
Cu N17 C16 C15 6.7(3) . . . . ?
N14 C15 C16 N17 -4.4(4) . . . . ?
N14 C15 C16 C21 176.4(3) . . . . ?
C16 N17 C18 C19 -0.7(4) . . . . ?
Cu N17 C18 C19 172.0(2) . . . . ?
N17 C18 C19 C20 0.9(5) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
N17 C16 C21 C20 1.3(4) . . . . ?
C15 C16 C21 C20 -179.6(3) . . . . ?
C19 C20 C21 C16 -1.1(4) . . . . ?
