#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/55/7015526.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_7015526
loop_
_publ_author_name
'Brotherton, Wendy S.'
'Guha, Pampa M.'
'Phan, Hoa'
'Clark, Ronald J.'
'Shatruk, Michael'
'Zhu, Lei'
_publ_section_title
;
 Tridentate complexes of
 2,6-bis(4-substituted-1,2,3-triazol-1-ylmethyl)pyridine and its
 organic azide precursors: an application of the copper(II)
 acetate-accelerated azide-alkyne cycloaddition.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3655
_journal_page_last               3665
_journal_paper_doi               10.1039/c0dt01702g
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C22 H22 Cl Cu N6, Cl O4'
_chemical_formula_sum            'C22 H22 Cl2 Cu N6 O4'
_chemical_formula_weight         568.90
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.990(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.8646(15)
_cell_length_b                   7.5283(7)
_cell_length_c                   18.9900(17)
_cell_measurement_reflns_used    6018
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.49
_cell_volume                     2339.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27253
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    1.205
_exptl_absorpt_correction_T_max  0.9312
_exptl_absorpt_correction_T_min  0.7137
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tetragonal
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+2.1237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                4194
_reflns_number_total             4787
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01702g.txt
_cod_data_source_block           zhu7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'EMPIRICAL' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7015526
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.876657(19) 0.91818(4) -0.050946(17) 0.01425(11) Uani 1 1 d . . .
C1 C 0.93702(17) 0.7096(4) 0.08594(16) 0.0199(6) Uani 1 1 d . . .
H1 H 0.9489 0.6178 0.0557 0.024 Uiso 1 1 calc R . .
C2 C 0.95372(18) 0.6817(4) 0.15967(16) 0.0239(6) Uani 1 1 d . . .
H2 H 0.9762 0.5721 0.1799 0.029 Uiso 1 1 calc R . .
C3 C 0.93723(19) 0.8158(4) 0.20375(17) 0.0271(7) Uani 1 1 d . . .
H3 H 0.9490 0.8002 0.2549 0.033 Uiso 1 1 calc R . .
C4 C 0.90328(18) 0.9731(4) 0.17259(16) 0.0259(7) Uani 1 1 d . . .
H4 H 0.8917 1.0671 0.2020 0.031 Uiso 1 1 calc R . .
C5 C 0.88634(16) 0.9913(4) 0.09759(15) 0.0180(6) Uani 1 1 d . . .
C6 C 0.84922(19) 1.1599(4) 0.06104(15) 0.0201(6) Uani 1 1 d . . .
H6A H 0.8013 1.1924 0.0798 0.024 Uiso 1 1 calc R . .
H6B H 0.8897 1.2572 0.0735 0.024 Uiso 1 1 calc R . .
C7 C 0.85141(17) 1.2926(4) -0.05739(15) 0.0180(6) Uani 1 1 d . . .
H7A H 0.9077 1.3268 -0.0319 0.022 Uiso 1 1 calc R . .
H7B H 0.8153 1.3966 -0.0581 0.022 Uiso 1 1 calc R . .
C8 C 0.84922(16) 1.2352(4) -0.13389(15) 0.0177(6) Uani 1 1 d . . .
C9 C 0.83444(18) 1.3509(4) -0.19200(16) 0.0241(6) Uani 1 1 d . . .
H9 H 0.8226 1.4724 -0.1857 0.029 Uiso 1 1 calc R . .
C10 C 0.8372(2) 1.2869(4) -0.25950(17) 0.0288(7) Uani 1 1 d . . .
H10 H 0.8269 1.3641 -0.3003 0.035 Uiso 1 1 calc R . .
C11 C 0.85482(19) 1.1098(4) -0.26739(17) 0.0272(7) Uani 1 1 d . . .
H11 H 0.8576 1.0640 -0.3133 0.033 Uiso 1 1 calc R . .
C12 C 0.86838(18) 1.0007(4) -0.20721(16) 0.0220(6) Uani 1 1 d . . .
H12 H 0.8803 0.8788 -0.2125 0.026 Uiso 1 1 calc R . .
C13 C 0.73256(17) 1.1253(4) -0.04487(16) 0.0191(6) Uani 1 1 d . . .
H13A H 0.7057 1.2086 -0.0175 0.023 Uiso 1 1 calc R . .
H13B H 0.7153 1.1566 -0.0970 0.023 Uiso 1 1 calc R . .
C14 C 0.70703(16) 0.9399(4) -0.03400(15) 0.0164(6) Uani 1 1 d . . .
C15 C 0.64670(17) 0.8686(4) -0.00549(15) 0.0181(6) Uani 1 1 d . . .
H15 H 0.6086 0.9297 0.0153 0.022 Uiso 1 1 calc R . .
C16 C 0.60756(17) 0.5512(4) 0.01107(16) 0.0212(6) Uani 1 1 d . . .
H16A H 0.5890 0.4645 -0.0287 0.025 Uiso 1 1 calc R . .
H16B H 0.5584 0.6033 0.0229 0.025 Uiso 1 1 calc R . .
C17 C 0.65719(17) 0.4556(4) 0.07703(15) 0.0178(6) Uani 1 1 d . . .
C18 C 0.62787(19) 0.2941(4) 0.09624(17) 0.0233(6) Uani 1 1 d . . .
H18 H 0.5786 0.2460 0.0673 0.028 Uiso 1 1 calc R . .
C19 C 0.6702(2) 0.2029(4) 0.15746(17) 0.0271(7) Uani 1 1 d . . .
H19 H 0.6496 0.0933 0.1704 0.033 Uiso 1 1 calc R . .
C20 C 0.74227(19) 0.2714(4) 0.19958(16) 0.0254(7) Uani 1 1 d . . .
H20 H 0.7712 0.2094 0.2415 0.031 Uiso 1 1 calc R . .
C21 C 0.77206(19) 0.4314(4) 0.18018(16) 0.0240(6) Uani 1 1 d . . .
H21 H 0.8218 0.4784 0.2086 0.029 Uiso 1 1 calc R . .
C22 C 0.72943(18) 0.5227(4) 0.11954(16) 0.0214(6) Uani 1 1 d . . .
H22 H 0.7500 0.6326 0.1069 0.026 Uiso 1 1 calc R . .
N1 N 0.90431(14) 0.8631(3) 0.05494(12) 0.0165(5) Uani 1 1 d . . .
N2 N 0.86521(14) 1.0613(3) -0.14145(13) 0.0175(5) Uani 1 1 d . . .
N3 N 0.82328(13) 1.1420(3) -0.01915(12) 0.0152(5) Uani 1 1 d . . .
N4 N 0.74719(14) 0.8043(3) -0.05739(12) 0.0168(5) Uani 1 1 d . . .
N5 N 0.71478(14) 0.6517(3) -0.04448(13) 0.0179(5) Uani 1 1 d . . .
N6 N 0.65387(14) 0.6917(3) -0.01365(13) 0.0168(5) Uani 1 1 d . . .
Cl1 Cl 0.94718(4) 0.69545(9) -0.08479(4) 0.02098(17) Uani 1 1 d . . .
Cl2 Cl 0.50782(5) 0.17913(13) 0.84842(4) 0.0369(2) Uani 1 1 d D . .
O1A O 0.5174(10) 0.162(2) 0.9244(5) 0.042(3) Uani 0.650(13) 1 d PD A 1
O2A O 0.4279(5) 0.2161(16) 0.8132(5) 0.069(3) Uani 0.650(13) 1 d PD A 1
O3A O 0.5254(5) -0.0056(10) 0.8284(3) 0.092(3) Uani 0.650(13) 1 d PD A 1
O4A O 0.5705(5) 0.2827(16) 0.8406(4) 0.105(4) Uani 0.650(13) 1 d PD A 1
O1B O 0.4996(19) 0.135(5) 0.9188(9) 0.041(6) Uani 0.350(13) 1 d PD A 2
O2B O 0.4380(8) 0.164(3) 0.7917(8) 0.057(5) Uani 0.350(13) 1 d PD A 2
O3B O 0.5758(7) 0.147(3) 0.8192(6) 0.087(7) Uani 0.350(13) 1 d PD A 2
O4B O 0.5149(10) 0.3857(12) 0.8467(5) 0.070(5) Uani 0.350(13) 1 d PD 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'
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'
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'
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
N1 Cu1 N2 158.38(10) . . ?
N1 Cu1 N3 83.52(9) . . ?
N2 Cu1 N3 81.57(9) . . ?
N1 Cu1 Cl1 97.06(7) . . ?
N2 Cu1 Cl1 96.00(7) . . ?
N3 Cu1 Cl1 173.38(7) . . ?
N1 Cu1 N4 87.94(9) . . ?
N2 Cu1 N4 105.06(9) . . ?
N3 Cu1 N4 81.15(8) . . ?
Cl1 Cu1 N4 105.45(6) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 117.2(2) . . ?
C4 C5 C6 120.9(3) . . ?
N3 C6 C5 112.5(2) . . ?
N3 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N3 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N3 C7 C8 108.4(2) . . ?
N3 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
N3 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
N2 C8 C9 121.9(3) . . ?
N2 C8 C7 114.9(2) . . ?
C9 C8 C7 123.2(3) . . ?
C8 C9 C10 118.8(3) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
N2 C12 C11 122.1(3) . . ?
N2 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C14 C13 N3 109.9(2) . . ?
C14 C13 H13A 109.7 . . ?
N3 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
N3 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N4 C14 C15 108.1(2) . . ?
N4 C14 C13 118.4(2) . . ?
C15 C14 C13 133.5(3) . . ?
N6 C15 C14 104.2(2) . . ?
N6 C15 H15 127.9 . . ?
C14 C15 H15 127.9 . . ?
N6 C16 C17 112.3(2) . . ?
N6 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N6 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C22 C17 C18 118.9(3) . . ?
C22 C17 C16 122.9(3) . . ?
C18 C17 C16 118.2(3) . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.6(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C5 N1 C1 118.7(2) . . ?
C5 N1 Cu1 115.32(19) . . ?
C1 N1 Cu1 126.0(2) . . ?
C12 N2 C8 118.8(2) . . ?
C12 N2 Cu1 126.9(2) . . ?
C8 N2 Cu1 114.29(19) . . ?
C7 N3 C6 112.5(2) . . ?
C7 N3 C13 109.1(2) . . ?
C6 N3 C13 111.5(2) . . ?
C7 N3 Cu1 105.45(16) . . ?
C6 N3 Cu1 109.38(16) . . ?
C13 N3 Cu1 108.63(16) . . ?
N5 N4 C14 109.4(2) . . ?
N5 N4 Cu1 137.56(17) . . ?
C14 N4 Cu1 104.01(17) . . ?
N4 N5 N6 106.4(2) . . ?
N5 N6 C15 111.9(2) . . ?
N5 N6 C16 120.4(2) . . ?
C15 N6 C16 127.5(2) . . ?
O4A Cl2 O2A 121.9(6) . . ?
O4A Cl2 O2B 120.0(8) . . ?
O4A Cl2 O3B 47.5(7) . . ?
O2A Cl2 O3B 129.5(7) . . ?
O2B Cl2 O3B 107.3(9) . . ?
O4A Cl2 O1B 119.9(13) . . ?
O2A Cl2 O1B 101.4(14) . . ?
O2B Cl2 O1B 116.8(14) . . ?
O3B Cl2 O1B 127.2(15) . . ?
O4A Cl2 O1A 105.3(8) . . ?
O2A Cl2 O1A 111.6(8) . . ?
O2B Cl2 O1A 130.2(9) . . ?
O3B Cl2 O1A 118.8(8) . . ?
O4A Cl2 O3A 107.6(6) . . ?
O2A Cl2 O3A 107.2(5) . . ?
O2B Cl2 O3A 84.8(8) . . ?
O3B Cl2 O3A 60.5(7) . . ?
O1B Cl2 O3A 95.2(15) . . ?
O1A Cl2 O3A 101.3(7) . . ?
O4A Cl2 O4B 49.9(6) . . ?
O2A Cl2 O4B 81.9(7) . . ?
O2B Cl2 O4B 96.9(9) . . ?
O3B Cl2 O4B 95.2(9) . . ?
O1B Cl2 O4B 106.3(15) . . ?
O1A Cl2 O4B 96.9(8) . . ?
O3A Cl2 O4B 154.6(6) . . ?
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
Cu1 N1 1.995(2) . ?
Cu1 N2 1.998(2) . ?
Cu1 N3 2.068(2) . ?
Cu1 Cl1 2.2380(7) . ?
Cu1 N4 2.321(2) . ?
C1 N1 1.352(4) . ?
C1 C2 1.376(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.341(4) . ?
C5 C6 1.508(4) . ?
C6 N3 1.485(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N3 1.485(3) . ?
C7 C8 1.508(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.351(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.380(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C12 N2 1.343(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.490(4) . ?
C13 N3 1.495(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.358(3) . ?
C14 C15 1.372(4) . ?
C15 N6 1.349(4) . ?
C15 H15 0.9500 . ?
C16 N6 1.458(4) . ?
C16 C17 1.510(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.384(4) . ?
C17 C18 1.394(4) . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N4 N5 1.320(3) . ?
N5 N6 1.334(3) . ?
Cl2 O4A 1.350(5) . ?
Cl2 O2A 1.381(7) . ?
Cl2 O2B 1.396(12) . ?
Cl2 O3B 1.409(9) . ?
Cl2 O1B 1.417(13) . ?
Cl2 O1A 1.417(9) . ?
Cl2 O3A 1.490(6) . ?
Cl2 O4B 1.561(8) . ?
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
N1 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 N1 -2.1(4) . . . . ?
C3 C4 C5 C6 179.9(3) . . . . ?
N1 C5 C6 N3 11.5(4) . . . . ?
C4 C5 C6 N3 -170.5(2) . . . . ?
N3 C7 C8 N2 -32.5(3) . . . . ?
N3 C7 C8 C9 149.3(3) . . . . ?
N2 C8 C9 C10 -0.8(4) . . . . ?
C7 C8 C9 C10 177.2(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C10 C11 C12 N2 -0.2(5) . . . . ?
N3 C13 C14 N4 -48.9(3) . . . . ?
N3 C13 C14 C15 133.3(3) . . . . ?
N4 C14 C15 N6 -0.2(3) . . . . ?
C13 C14 C15 N6 177.8(3) . . . . ?
N6 C16 C17 C22 15.7(4) . . . . ?
N6 C16 C17 C18 -165.4(2) . . . . ?
C22 C17 C18 C19 0.6(4) . . . . ?
C16 C17 C18 C19 -178.4(3) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C17 -0.6(4) . . . . ?
C18 C17 C22 C21 0.0(4) . . . . ?
C16 C17 C22 C21 178.9(3) . . . . ?
C4 C5 N1 C1 2.5(4) . . . . ?
C6 C5 N1 C1 -179.4(2) . . . . ?
C4 C5 N1 Cu1 -179.0(2) . . . . ?
C6 C5 N1 Cu1 -0.9(3) . . . . ?
C2 C1 N1 C5 -1.1(4) . . . . ?
C2 C1 N1 Cu1 -179.5(2) . . . . ?
N2 Cu1 N1 C5 40.1(4) . . . . ?
N3 Cu1 N1 C5 -6.52(19) . . . . ?
Cl1 Cu1 N1 C5 166.84(18) . . . . ?
N4 Cu1 N1 C5 -87.8(2) . . . . ?
N2 Cu1 N1 C1 -141.5(3) . . . . ?
N3 Cu1 N1 C1 171.9(2) . . . . ?
Cl1 Cu1 N1 C1 -14.8(2) . . . . ?
N4 Cu1 N1 C1 90.6(2) . . . . ?
C11 C12 N2 C8 -0.8(4) . . . . ?
C11 C12 N2 Cu1 176.0(2) . . . . ?
C9 C8 N2 C12 1.4(4) . . . . ?
C7 C8 N2 C12 -176.8(2) . . . . ?
C9 C8 N2 Cu1 -175.9(2) . . . . ?
C7 C8 N2 Cu1 5.9(3) . . . . ?
N1 Cu1 N2 C12 150.8(3) . . . . ?
N3 Cu1 N2 C12 -162.3(2) . . . . ?
Cl1 Cu1 N2 C12 23.9(2) . . . . ?
N4 Cu1 N2 C12 -83.9(2) . . . . ?
N1 Cu1 N2 C8 -32.2(4) . . . . ?
N3 Cu1 N2 C8 14.68(19) . . . . ?
Cl1 Cu1 N2 C8 -159.11(18) . . . . ?
N4 Cu1 N2 C8 93.1(2) . . . . ?
C8 C7 N3 C6 160.3(2) . . . . ?
C8 C7 N3 C13 -75.3(3) . . . . ?
C8 C7 N3 Cu1 41.2(2) . . . . ?
C5 C6 N3 C7 -132.4(2) . . . . ?
C5 C6 N3 C13 104.6(3) . . . . ?
C5 C6 N3 Cu1 -15.5(3) . . . . ?
C14 C13 N3 C7 155.6(2) . . . . ?
C14 C13 N3 C6 -79.5(3) . . . . ?
C14 C13 N3 Cu1 41.1(3) . . . . ?
N1 Cu1 N3 C7 133.34(17) . . . . ?
N2 Cu1 N3 C7 -30.96(17) . . . . ?
N4 Cu1 N3 C7 -137.75(17) . . . . ?
N1 Cu1 N3 C6 12.14(17) . . . . ?
N2 Cu1 N3 C6 -152.16(18) . . . . ?
N4 Cu1 N3 C6 101.05(17) . . . . ?
N1 Cu1 N3 C13 -109.82(18) . . . . ?
N2 Cu1 N3 C13 85.89(18) . . . . ?
N4 Cu1 N3 C13 -20.90(17) . . . . ?
C15 C14 N4 N5 -0.2(3) . . . . ?
C13 C14 N4 N5 -178.6(2) . . . . ?
C15 C14 N4 Cu1 -153.62(19) . . . . ?
C13 C14 N4 Cu1 28.0(3) . . . . ?
N1 Cu1 N4 N5 -60.2(3) . . . . ?
N2 Cu1 N4 N5 137.3(3) . . . . ?
N3 Cu1 N4 N5 -144.0(3) . . . . ?
Cl1 Cu1 N4 N5 36.6(3) . . . . ?
N1 Cu1 N4 C14 81.02(18) . . . . ?
N2 Cu1 N4 C14 -81.46(18) . . . . ?
N3 Cu1 N4 C14 -2.74(17) . . . . ?
Cl1 Cu1 N4 C14 177.78(15) . . . . ?
C14 N4 N5 N6 0.6(3) . . . . ?
Cu1 N4 N5 N6 140.5(2) . . . . ?
N4 N5 N6 C15 -0.7(3) . . . . ?
N4 N5 N6 C16 -176.8(2) . . . . ?
C14 C15 N6 N5 0.6(3) . . . . ?
C14 C15 N6 C16 176.3(3) . . . . ?
C17 C16 N6 N5 70.4(3) . . . . ?
C17 C16 N6 C15 -105.0(3) . . . . ?
