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#$Date: 2024-01-06 10:43:36 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/28/7062819.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_7062819
loop_
_publ_author_name
'Malakar, Kakoli'
'Selvakumaran, Balasubramaniam'
'Murali, Mariappan'
'Arul Prakash, Pitchan'
'Sangeetha, Somasundaram'
'Sohtun, Winaki P.'
'Jaabir, Mohamed Sultan Mohamed'
'Velusamy, Marappan'
_publ_section_title
;
 Copper(ii) complexes of the CuN4S core: selective cytotoxicity to
 cancerous cells, ROS generation and induction of apoptosis
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20070
_journal_page_last               20087
_journal_paper_doi               10.1039/D2NJ06170H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C23 H19 Cu N6 S2, Cl O4'
_chemical_formula_sum            'C23 H19 Cl Cu N6 O4 S2'
_chemical_formula_weight         606.55
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-01-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2022-10-19 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.427(11)
_cell_angle_beta                 99.066(11)
_cell_angle_gamma                94.234(11)
_cell_formula_units_Z            2
_cell_length_a                   8.0120(17)
_cell_length_b                   11.649(2)
_cell_length_c                   13.796(3)
_cell_measurement_reflns_used    5256
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.65
_cell_measurement_theta_min      2.51
_cell_volume                     1251.6(4)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42085
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.739
_diffrn_reflns_theta_min         1.514
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             618
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0436
_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)+(0.0509P)²+0.3765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4310
_reflns_number_total             6411
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj06170h2.cif
_cod_data_source_block           aa
_cod_depositor_comments
'Adding full bibliography for 7062815--7062821.cif.'
_cod_original_cell_volume        1251.6(5)
_cod_database_code               7062819
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N6(H6), C12(H12), C21(H21), C20(H20), C19(H19), C1(H1), C13(H13), C2(H2),
 C4(H4), C14(H14), C3(H3), C17(H17), C16(H16)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cu1 Cu 0.59062(4) 0.31619(3) 0.23071(2) 0.03402(11) Uani 1 1 d . . . . .
S1 S 0.30018(9) 0.28910(7) 0.18142(6) 0.04222(19) Uani 1 1 d . . . . .
Cl1 Cl 1.27969(12) 0.21898(7) 0.68205(6) 0.0548(2) Uani 1 1 d . . . . .
S2 S 0.06814(10) 0.12832(7) 0.25243(7) 0.0494(2) Uani 1 1 d . . . . .
N4 N 0.6594(3) 0.16230(19) 0.13704(17) 0.0341(5) Uani 1 1 d . . . . .
N1 N 0.8096(3) 0.3672(2) 0.32942(16) 0.0355(5) Uani 1 1 d . . . . .
N2 N 0.5424(3) 0.2343(2) 0.33970(17) 0.0363(5) Uani 1 1 d . . . . .
N3 N 0.6589(3) 0.39006(19) 0.11901(16) 0.0333(5) Uani 1 1 d . . . . .
N5 N 0.3875(3) 0.1733(2) 0.33809(18) 0.0390(5) Uani 1 1 d . . . . .
N6 N 0.9708(3) 0.3153(2) 0.45928(17) 0.0402(6) Uani 1 1 d . . . . .
H6 H 1.000520 0.280603 0.509231 0.048 Uiso 1 1 calc R U . . .
C22 C 0.7232(3) 0.3182(2) 0.04991(19) 0.0329(6) Uani 1 1 d . . . . .
C23 C 0.7212(3) 0.1967(2) 0.0588(2) 0.0349(6) Uani 1 1 d . . . . .
C7 C 0.8174(4) 0.3012(2) 0.4008(2) 0.0365(6) Uani 1 1 d . . . . .
C8 C 0.6670(4) 0.2272(2) 0.4103(2) 0.0368(6) Uani 1 1 d . . . . .
C5 C 1.0721(4) 0.3958(2) 0.4245(2) 0.0373(6) Uani 1 1 d . . . . .
C6 C 0.9693(3) 0.4284(2) 0.3425(2) 0.0344(6) Uani 1 1 d . . . . .
C10 C 0.2737(4) 0.1965(2) 0.2661(2) 0.0373(6) Uani 1 1 d . . . . .
C12 C 0.6520(4) 0.0494(2) 0.1443(2) 0.0445(7) Uani 1 1 d . . . . .
H12 H 0.609667 0.024915 0.197659 0.053 Uiso 1 1 calc R U . . .
C21 C 0.6597(4) 0.5031(2) 0.1111(2) 0.0405(7) Uani 1 1 d . . . . .
H21 H 0.616632 0.552689 0.158217 0.049 Uiso 1 1 calc R U . . .
C18 C 0.7876(4) 0.3593(3) -0.0292(2) 0.0429(7) Uani 1 1 d . . . . .
C15 C 0.7808(4) 0.1191(3) -0.0131(2) 0.0434(7) Uani 1 1 d . . . . .
C20 C 0.7226(4) 0.5494(3) 0.0352(2) 0.0464(8) Uani 1 1 d . . . . .
H20 H 0.721409 0.628644 0.032339 0.056 Uiso 1 1 calc R U . . .
C19 C 0.7858(4) 0.4787(3) -0.0349(3) 0.0498(8) Uani 1 1 d . . . . .
H19 H 0.827420 0.509042 -0.086064 0.060 Uiso 1 1 calc R U . . .
C1 C 1.0341(4) 0.5132(3) 0.2930(2) 0.0424(7) Uani 1 1 d . . . . .
H1 H 0.967492 0.538225 0.240088 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7051(4) -0.0339(3) 0.0750(3) 0.0504(8) Uani 1 1 d . . . . .
H13 H 0.695640 -0.112309 0.081671 0.060 Uiso 1 1 calc R U . . .
C2 C 1.1997(4) 0.5583(3) 0.3253(2) 0.0481(8) Uani 1 1 d . . . . .
H2 H 1.246377 0.613745 0.292584 0.058 Uiso 1 1 calc R U . . .
C4 C 1.2393(4) 0.4415(3) 0.4567(2) 0.0493(8) Uani 1 1 d . . . . .
H4 H 1.306600 0.417749 0.510001 0.059 Uiso 1 1 calc R U . . .
O2 O 1.3777(5) 0.3204(3) 0.6708(3) 0.1133(12) Uani 1 1 d . . . . .
O3 O 1.2225(5) 0.2336(3) 0.7741(2) 0.1113(13) Uani 1 1 d . . . . .
C14 C 0.7707(4) 0.0007(3) -0.0022(3) 0.0524(8) Uani 1 1 d . . . . .
H14 H 0.808895 -0.053838 -0.047867 0.063 Uiso 1 1 calc R U . . .
C3 C 1.3010(4) 0.5235(3) 0.4061(3) 0.0531(8) Uani 1 1 d . . . . .
H3 H 1.412597 0.556808 0.425802 0.064 Uiso 1 1 calc R U . . .
C17 C 0.8538(5) 0.2778(3) -0.0985(3) 0.0581(9) Uani 1 1 d . . . . .
H17 H 0.900625 0.304402 -0.149602 0.070 Uiso 1 1 calc R U . . .
C9 C 0.6615(4) 0.1556(3) 0.4905(2) 0.0546(9) Uani 1 1 d . . . . .
H9A H 0.561404 0.167763 0.519296 0.082 Uiso 1 1 calc R U . . .
H9B H 0.760433 0.177958 0.540881 0.082 Uiso 1 1 calc R U . . .
H9C H 0.659140 0.074645 0.463273 0.082 Uiso 1 1 calc R U . . .
C16 C 0.8496(5) 0.1640(3) -0.0911(3) 0.0587(9) Uani 1 1 d . . . . .
H16 H 0.892221 0.113316 -0.137585 0.070 Uiso 1 1 calc R U . . .
O4 O 1.3627(6) 0.1183(3) 0.6734(3) 0.1353(16) Uani 1 1 d . . . . .
O1 O 1.1368(6) 0.1997(4) 0.6063(3) 0.1485(18) Uani 1 1 d . . . . .
C11 C 0.0874(5) 0.0373(3) 0.3470(3) 0.0710(11) Uani 1 1 d . . . . .
H11A H 0.169838 -0.016552 0.335029 0.106 Uiso 1 1 calc R U . . .
H11B H -0.020486 -0.005216 0.345548 0.106 Uiso 1 1 calc R U . . .
H11C H 0.123228 0.084888 0.410915 0.106 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'
S S 0.1246 0.1234 '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
N4 Cu1 S1 98.89(6) . . ?
N1 Cu1 S1 154.84(7) . . ?
N1 Cu1 N4 102.09(9) . . ?
N2 Cu1 S1 83.79(7) . . ?
N2 Cu1 N4 95.98(9) . . ?
N2 Cu1 N1 80.37(9) . . ?
N2 Cu1 N3 174.37(9) . . ?
N3 Cu1 S1 100.36(7) . . ?
N3 Cu1 N4 79.68(9) . . ?
N3 Cu1 N1 96.94(9) . . ?
C10 S1 Cu1 92.90(10) . . ?
O3 Cl1 O2 111.0(2) . . ?
O4 Cl1 O2 114.4(3) . . ?
O4 Cl1 O3 108.6(2) . . ?
O4 Cl1 O1 106.6(3) . . ?
O1 Cl1 O2 108.0(2) . . ?
O1 Cl1 O3 108.1(3) . . ?
C10 S2 C11 102.67(16) . . ?
C23 N4 Cu1 109.21(17) . . ?
C12 N4 Cu1 132.8(2) . . ?
C12 N4 C23 118.0(2) . . ?
C7 N1 Cu1 108.81(18) . . ?
C7 N1 C6 105.8(2) . . ?
C6 N1 Cu1 143.82(18) . . ?
N5 N2 Cu1 122.63(17) . . ?
C8 N2 Cu1 118.12(19) . . ?
C8 N2 N5 118.8(2) . . ?
C22 N3 Cu1 115.40(17) . . ?
C21 N3 Cu1 126.0(2) . . ?
C21 N3 C22 118.3(2) . . ?
C10 N5 N2 110.7(2) . . ?
C7 N6 H6 126.2 . . ?
C7 N6 C5 107.6(2) . . ?
C5 N6 H6 126.2 . . ?
N3 C22 C23 117.9(2) . . ?
N3 C22 C18 122.0(2) . . ?
C18 C22 C23 120.1(3) . . ?
N4 C23 C22 117.5(2) . . ?
N4 C23 C15 123.0(2) . . ?
C15 C23 C22 119.5(2) . . ?
N1 C7 N6 112.4(2) . . ?
N1 C7 C8 120.1(2) . . ?
N6 C7 C8 127.5(2) . . ?
N2 C8 C7 110.3(2) . . ?
N2 C8 C9 125.9(3) . . ?
C7 C8 C9 123.8(3) . . ?
N6 C5 C6 105.8(2) . . ?
N6 C5 C4 131.7(3) . . ?
C4 C5 C6 122.6(3) . . ?
N1 C6 C5 108.5(2) . . ?
N1 C6 C1 131.8(3) . . ?
C1 C6 C5 119.7(3) . . ?
S1 C10 S2 114.37(17) . . ?
N5 C10 S1 128.0(2) . . ?
N5 C10 S2 117.6(2) . . ?
N4 C12 H12 118.6 . . ?
N4 C12 C13 122.8(3) . . ?
C13 C12 H12 118.6 . . ?
N3 C21 H21 118.7 . . ?
N3 C21 C20 122.5(3) . . ?
C20 C21 H21 118.7 . . ?
C22 C18 C17 118.4(3) . . ?
C19 C18 C22 117.8(3) . . ?
C19 C18 C17 123.7(3) . . ?
C23 C15 C14 117.0(3) . . ?
C23 C15 C16 119.1(3) . . ?
C14 C15 C16 123.9(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.0 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C6 C1 H1 121.3 . . ?
C2 C1 C6 117.4(3) . . ?
C2 C1 H1 121.3 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C5 C4 H4 121.6 . . ?
C3 C4 C5 116.7(3) . . ?
C3 C4 H4 121.6 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C18 C17 H17 119.3 . . ?
C16 C17 C18 121.5(3) . . ?
C16 C17 H17 119.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.3 . . ?
S2 C11 H11A 109.5 . . ?
S2 C11 H11B 109.5 . . ?
S2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
Cu1 S1 2.3037(9) . ?
Cu1 N4 2.209(2) . ?
Cu1 N1 2.035(2) . ?
Cu1 N2 1.967(2) . ?
Cu1 N3 2.000(2) . ?
S1 C10 1.729(3) . ?
Cl1 O2 1.411(3) . ?
Cl1 O3 1.409(3) . ?
Cl1 O4 1.390(3) . ?
Cl1 O1 1.403(3) . ?
S2 C10 1.744(3) . ?
S2 C11 1.793(4) . ?
N4 C23 1.355(3) . ?
N4 C12 1.331(3) . ?
N1 C7 1.332(3) . ?
N1 C6 1.390(3) . ?
N2 N5 1.379(3) . ?
N2 C8 1.297(3) . ?
N3 C22 1.364(3) . ?
N3 C21 1.337(3) . ?
N5 C10 1.311(4) . ?
N6 H6 0.8600 . ?
N6 C7 1.345(3) . ?
N6 C5 1.381(4) . ?
C22 C23 1.437(4) . ?
C22 C18 1.408(4) . ?
C23 C15 1.407(4) . ?
C7 C8 1.464(4) . ?
C8 C9 1.484(4) . ?
C5 C6 1.408(4) . ?
C5 C4 1.383(4) . ?
C6 C1 1.396(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.398(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(4) . ?
C18 C19 1.405(4) . ?
C18 C17 1.437(4) . ?
C15 C14 1.408(4) . ?
C15 C16 1.429(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.362(5) . ?
C19 H19 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.370(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.358(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.371(4) . ?
C14 H14 0.9300 . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.343(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C16 H16 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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
Cu1 S1 C10 S2 -171.87(14) . . . . ?
Cu1 S1 C10 N5 8.8(3) . . . . ?
Cu1 N4 C23 C22 -2.5(3) . . . . ?
Cu1 N4 C23 C15 178.1(2) . . . . ?
Cu1 N4 C12 C13 -179.4(2) . . . . ?
Cu1 N1 C7 N6 169.15(19) . . . . ?
Cu1 N1 C7 C8 -12.7(3) . . . . ?
Cu1 N1 C6 C5 -162.3(2) . . . . ?
Cu1 N1 C6 C1 20.5(5) . . . . ?
Cu1 N2 N5 C10 -11.9(3) . . . . ?
Cu1 N2 C8 C7 9.4(3) . . . . ?
Cu1 N2 C8 C9 -170.8(2) . . . . ?
Cu1 N3 C22 C23 5.5(3) . . . . ?
Cu1 N3 C22 C18 -175.6(2) . . . . ?
Cu1 N3 C21 C20 174.5(2) . . . . ?
N4 C23 C15 C14 1.3(4) . . . . ?
N4 C23 C15 C16 -177.7(3) . . . . ?
N4 C12 C13 C14 1.4(5) . . . . ?
N1 C7 C8 N2 3.0(4) . . . . ?
N1 C7 C8 C9 -176.8(3) . . . . ?
N1 C6 C1 C2 179.2(3) . . . . ?
N2 N5 C10 S1 -0.2(4) . . . . ?
N2 N5 C10 S2 -179.50(18) . . . . ?
N3 C22 C23 N4 -1.7(4) . . . . ?
N3 C22 C23 C15 177.7(2) . . . . ?
N3 C22 C18 C19 0.7(4) . . . . ?
N3 C22 C18 C17 179.7(3) . . . . ?
N3 C21 C20 C19 0.3(5) . . . . ?
N5 N2 C8 C7 -177.9(2) . . . . ?
N5 N2 C8 C9 1.9(4) . . . . ?
N6 C7 C8 N2 -179.1(3) . . . . ?
N6 C7 C8 C9 1.1(5) . . . . ?
N6 C5 C6 N1 -0.1(3) . . . . ?
N6 C5 C6 C1 177.5(3) . . . . ?
N6 C5 C4 C3 -178.4(3) . . . . ?
C22 N3 C21 C20 0.3(4) . . . . ?
C22 C23 C15 C14 -178.0(3) . . . . ?
C22 C23 C15 C16 2.9(4) . . . . ?
C22 C18 C19 C20 -0.1(5) . . . . ?
C22 C18 C17 C16 2.4(5) . . . . ?
C23 N4 C12 C13 0.0(4) . . . . ?
C23 C22 C18 C19 179.6(3) . . . . ?
C23 C22 C18 C17 -1.4(4) . . . . ?
C23 C15 C14 C13 0.2(5) . . . . ?
C23 C15 C16 C17 -1.9(5) . . . . ?
C7 N1 C6 C5 0.1(3) . . . . ?
C7 N1 C6 C1 -177.1(3) . . . . ?
C7 N6 C5 C6 0.2(3) . . . . ?
C7 N6 C5 C4 -179.8(3) . . . . ?
C8 N2 N5 C10 175.7(2) . . . . ?
C5 N6 C7 N1 -0.1(3) . . . . ?
C5 N6 C7 C8 -178.2(3) . . . . ?
C5 C6 C1 C2 2.3(4) . . . . ?
C5 C4 C3 C2 -0.5(5) . . . . ?
C6 N1 C7 N6 0.0(3) . . . . ?
C6 N1 C7 C8 178.2(2) . . . . ?
C6 C5 C4 C3 1.6(5) . . . . ?
C6 C1 C2 C3 -1.3(5) . . . . ?
C12 N4 C23 C22 177.9(2) . . . . ?
C12 N4 C23 C15 -1.5(4) . . . . ?
C12 C13 C14 C15 -1.5(5) . . . . ?
C21 N3 C22 C23 -179.8(2) . . . . ?
C21 N3 C22 C18 -0.8(4) . . . . ?
C21 C20 C19 C18 -0.4(5) . . . . ?
C18 C22 C23 N4 179.3(2) . . . . ?
C18 C22 C23 C15 -1.3(4) . . . . ?
C18 C17 C16 C15 -0.8(6) . . . . ?
C19 C18 C17 C16 -178.7(3) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C4 C5 C6 N1 179.9(3) . . . . ?
C4 C5 C6 C1 -2.5(5) . . . . ?
C14 C15 C16 C17 179.1(4) . . . . ?
C17 C18 C19 C20 -179.0(3) . . . . ?
C16 C15 C14 C13 179.2(3) . . . . ?
C11 S2 C10 S1 178.14(19) . . . . ?
C11 S2 C10 N5 -2.5(3) . . . . ?
