#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:48:32 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063264.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_7063264
loop_
_publ_author_name
'Xue, Xuan-Yi'
'He, Jing-Liang'
'Li, Rui'
'Ding, Bo'
'Wu, Wen-Long'
'Cao, Yao-Yao'
'He, Ran'
'Hu, Peng-Hong'
'Ji, Jing'
'Shi, Da-Hua'
_publ_section_title
;
 Design, synthesis and anticancer evaluation of imamine-1,3,5-triazine
 derivatives
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12188
_journal_page_last               12198
_journal_paper_doi               10.1039/D4NJ00819G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C23 H24 Cl N9, C H Cl3'
_chemical_formula_sum            'C24 H25 Cl4 N9'
_chemical_formula_weight         581.33
_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     dual
_audit_creation_date             2023-06-17
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-02-02 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                105.816(5)
_cell_angle_beta                 107.239(6)
_cell_angle_gamma                101.579(6)
_cell_formula_units_Z            2
_cell_length_a                   9.478(4)
_cell_length_b                   12.216(5)
_cell_length_c                   13.705(6)
_cell_measurement_reflns_used    3076
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.33
_cell_volume                     1388.1(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.964
_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  0.0214
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8622
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         1.664
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5521
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1038 before and 0.0362 after correction.
The Ratio of minimum to maximum transmission is 0.7405.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6174
_refine_ls_number_restraints     103
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0806
_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)+(0.1341P)²+1.0534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2349
_refine_ls_wR_factor_ref         0.2625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4128
_reflns_number_total             6174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00819g2.cif
_cod_data_source_block           20230616_0m
_cod_depositor_comments          'Adding full bibliography for 7063264.cif.'
_cod_database_code               7063264
_shelx_shelxl_version_number     2016/4
_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_max   0.951
_shelx_estimated_absorpt_t_min   0.910
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B)
4.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N4(H4), C15(H15), C7(H7), C13(H13), C5(H5A), C3(H3), C8(H8), C12(H12),
  C1(H1), C2(H2)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_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
Cl1 Cl 0.95778(13) 1.05703(10) 0.88031(8) 0.0796(4) Uani 1 1 d . U . . .
Cl2 Cl -0.0403(2) 0.3514(2) 0.37114(19) 0.1359(7) Uani 1 1 d . U . . .
Cl3 Cl -0.2928(2) 0.19275(19) 0.1770(2) 0.1460(8) Uani 1 1 d . U . . .
Cl4 Cl -0.0040(3) 0.3116(3) 0.1671(2) 0.1742(11) Uani 1 1 d . U . . .
N2 N 0.5812(3) 0.4511(2) 0.25382(19) 0.0405(6) Uani 1 1 d . U . . .
N5 N 0.8987(3) 0.8358(2) 0.51071(19) 0.0440(6) Uani 1 1 d . U . . .
H5 H 0.804089 0.814109 0.506057 0.053 Uiso 1 1 calc R U . . .
N8 N 0.9336(3) 0.9414(2) 0.6843(2) 0.0484(7) Uani 1 1 d . U . . .
N4 N 0.6655(3) 0.5452(2) 0.14574(19) 0.0499(7) Uani 1 1 d . U . . .
H4 H 0.652225 0.544206 0.080626 0.060 Uiso 1 1 calc R U . . .
N6 N 1.1464(3) 0.9640(2) 0.6245(2) 0.0502(7) Uani 1 1 d . U . . .
N3 N 0.4322(3) 0.3979(3) 0.0644(2) 0.0518(7) Uani 1 1 d . U . . .
N7 N 1.1814(3) 1.0749(3) 0.8075(2) 0.0552(8) Uani 1 1 d . U . . .
N1 N 0.4120(4) 0.2827(3) 0.4923(2) 0.0554(7) Uani 1 1 d . U . . .
C10 C 0.8002(3) 0.6324(3) 0.2320(2) 0.0395(7) Uani 1 1 d . U . . .
C6 C 0.4762(3) 0.3644(3) 0.2594(2) 0.0402(6) Uani 1 1 d . U . . .
C9 C 0.5557(3) 0.4633(3) 0.1564(2) 0.0412(7) Uani 1 1 d . U . . .
C14 C 0.9227(3) 0.7805(3) 0.4147(2) 0.0385(6) Uani 1 1 d . U . . .
C4 C 0.5055(3) 0.3570(3) 0.3701(2) 0.0409(7) Uani 1 1 d . U . . .
C17 C 0.9981(4) 0.9165(3) 0.6080(2) 0.0426(7) Uani 1 1 d . U . . .
C11 C 0.9387(4) 0.6573(3) 0.2136(2) 0.0438(7) Uani 1 1 d . U . . .
C15 C 0.7927(3) 0.6937(3) 0.3306(2) 0.0416(7) Uani 1 1 d . U . . .
H15 H 0.699115 0.676643 0.340796 0.050 Uiso 1 1 calc R U . . .
C19 C 1.0338(4) 1.0203(3) 0.7780(3) 0.0495(8) Uani 1 1 d . U . . .
N20 N 1.3844(4) 1.0933(4) 0.7454(3) 0.0817(12) Uani 1 1 d . U . . .
C7 C 0.3508(4) 0.2872(3) 0.1672(3) 0.0525(8) Uani 1 1 d . U . . .
H7 H 0.281081 0.223456 0.169679 0.063 Uiso 1 1 calc R U . . .
C13 C 1.0608(4) 0.8072(3) 0.3975(3) 0.0505(8) Uani 1 1 d . U . . .
H13 H 1.148811 0.865828 0.451806 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3925(4) 0.2902(3) 0.3933(3) 0.0498(8) Uani 1 1 d . U . . .
H5A H 0.296839 0.247696 0.336954 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6461(4) 0.4202(3) 0.4542(3) 0.0541(8) Uani 1 1 d . U . . .
H3 H 0.724552 0.467714 0.442357 0.065 Uiso 1 1 calc R U . . .
C18 C 1.2332(4) 1.0426(3) 0.7250(3) 0.0550(9) Uani 1 1 d . U . . .
C8 C 0.3334(4) 0.3086(3) 0.0715(3) 0.0569(9) Uani 1 1 d . U . . .
H8 H 0.248799 0.258465 0.008715 0.068 Uiso 1 1 calc R U . . .
C12 C 1.0652(4) 0.7452(3) 0.2982(3) 0.0542(9) Uani 1 1 d . U . . .
H12 H 1.158355 0.763607 0.287702 0.065 Uiso 1 1 calc R U . . .
C1 C 0.5500(4) 0.3435(4) 0.5714(3) 0.0583(9) Uani 1 1 d . U . . .
H1 H 0.566226 0.339160 0.640378 0.070 Uiso 1 1 calc R U . . .
C2 C 0.6703(4) 0.4126(4) 0.5566(3) 0.0633(10) Uani 1 1 d . U . . .
H2 H 0.765424 0.453193 0.613951 0.076 Uiso 1 1 calc R U . . .
C16 C 0.9538(4) 0.5929(4) 0.1084(3) 0.0621(10) Uani 1 1 d . U . . .
H16A H 0.920252 0.630339 0.056340 0.093 Uiso 1 1 calc R U . . .
H16B H 0.890583 0.510937 0.079934 0.093 Uiso 1 1 calc R U . . .
H16C H 1.060265 0.596398 0.121903 0.093 Uiso 1 1 calc R U . . .
C21 C 1.4462(5) 1.0652(4) 0.6553(4) 0.0790(13) Uani 1 1 d . U . . .
H21A H 1.366787 1.051830 0.585847 0.095 Uiso 1 1 calc R U . . .
H21B H 1.534659 1.131320 0.669279 0.095 Uiso 1 1 calc R U . . .
C23 C 1.4956(6) 1.1623(6) 0.8601(5) 0.126(2) Uani 1 1 d . U . . .
H23A H 1.435849 1.183538 0.904744 0.151 Uiso 1 1 calc R U . . .
H23B H 1.548049 1.109387 0.886111 0.151 Uiso 1 1 calc R U . . .
C22 C 1.4918(8) 0.9592(6) 0.6524(6) 0.125(2) Uani 1 1 d . U . . .
H22A H 1.529408 0.937878 0.594240 0.187 Uiso 1 1 calc R U . . .
H22B H 1.403991 0.894811 0.640123 0.187 Uiso 1 1 calc R U . . .
H22C H 1.572420 0.974095 0.720722 0.187 Uiso 1 1 calc R U . . .
C25 C -0.1322(7) 0.3217(6) 0.2347(6) 0.1125(19) Uani 1 1 d . U . . .
H25 H -0.170620 0.388933 0.227156 0.135 Uiso 1 1 calc R U . . .
C24 C 1.6041(9) 1.2621(8) 0.8777(6) 0.160(3) Uani 1 1 d . U . . .
H24A H 1.686046 1.283860 0.947163 0.240 Uiso 1 1 calc R U . . .
H24B H 1.558583 1.325542 0.877551 0.240 Uiso 1 1 calc R U . . .
H24C H 1.645386 1.248402 0.820954 0.240 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'
N N 0.0061 0.0033 '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
C6 N2 C9 117.2(2) . . ?
C14 N5 H5 114.5 . . ?
C17 N5 H5 114.5 . . ?
C17 N5 C14 131.1(3) . . ?
C19 N8 C17 112.2(3) . . ?
C10 N4 H4 116.8 . . ?
C9 N4 H4 116.8 . . ?
C9 N4 C10 126.4(2) . . ?
C17 N6 C18 114.9(3) . . ?
C8 N3 C9 115.5(3) . . ?
C19 N7 C18 112.2(3) . . ?
C1 N1 C5 116.9(3) . . ?
C11 C10 N4 118.6(3) . . ?
C15 C10 N4 120.7(3) . . ?
C15 C10 C11 120.7(3) . . ?
N2 C6 C4 115.5(2) . . ?
N2 C6 C7 121.1(3) . . ?
C7 C6 C4 123.4(3) . . ?
N2 C9 N4 118.9(2) . . ?
N2 C9 N3 125.8(3) . . ?
N3 C9 N4 115.3(3) . . ?
C15 C14 N5 115.2(3) . . ?
C13 C14 N5 125.9(3) . . ?
C13 C14 C15 118.8(3) . . ?
C5 C4 C6 121.8(3) . . ?
C3 C4 C6 120.6(3) . . ?
C3 C4 C5 117.5(3) . . ?
N5 C17 N8 114.0(3) . . ?
N6 C17 N5 120.9(3) . . ?
N6 C17 N8 125.1(3) . . ?
C10 C11 C16 123.0(3) . . ?
C12 C11 C10 116.6(3) . . ?
C12 C11 C16 120.4(3) . . ?
C10 C15 C14 121.2(3) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
N8 C19 Cl1 114.6(2) . . ?
N7 C19 Cl1 115.0(2) . . ?
N7 C19 N8 130.4(3) . . ?
C18 N20 C21 120.1(3) . . ?
C18 N20 C23 120.1(4) . . ?
C23 N20 C21 119.2(4) . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.1(3) . . ?
C8 C7 H7 121.4 . . ?
C14 C13 H13 120.6 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.6 . . ?
N1 C5 C4 124.1(3) . . ?
N1 C5 H5A 118.0 . . ?
C4 C5 H5A 118.0 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
N6 C18 N7 125.2(3) . . ?
N6 C18 N20 117.0(3) . . ?
N20 C18 N7 117.8(3) . . ?
N3 C8 C7 123.1(3) . . ?
N3 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C11 C12 H12 118.1 . . ?
C13 C12 C11 123.7(3) . . ?
C13 C12 H12 118.1 . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.5(3) . . ?
C2 C1 H1 118.3 . . ?
C3 C2 H2 120.8 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N20 C21 H21A 110.2 . . ?
N20 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C22 C21 N20 107.7(5) . . ?
C22 C21 H21A 110.2 . . ?
C22 C21 H21B 110.2 . . ?
N20 C23 H23A 107.9 . . ?
N20 C23 H23B 107.9 . . ?
H23A C23 H23B 107.2 . . ?
C24 C23 N20 117.6(7) . . ?
C24 C23 H23A 107.9 . . ?
C24 C23 H23B 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl2 C25 Cl3 110.7(4) . . ?
Cl2 C25 Cl4 111.0(3) . . ?
Cl2 C25 H25 107.7 . . ?
Cl3 C25 H25 107.7 . . ?
Cl4 C25 Cl3 111.9(4) . . ?
Cl4 C25 H25 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
Cl1 C19 1.754(3) . ?
Cl2 C25 1.711(8) . ?
Cl3 C25 1.752(7) . ?
Cl4 C25 1.737(7) . ?
N2 C6 1.335(4) . ?
N2 C9 1.339(4) . ?
N5 H5 0.8600 . ?
N5 C14 1.413(4) . ?
N5 C17 1.343(4) . ?
N8 C17 1.356(4) . ?
N8 C19 1.310(4) . ?
N4 H4 0.8600 . ?
N4 C10 1.427(4) . ?
N4 C9 1.363(4) . ?
N6 C17 1.334(4) . ?
N6 C18 1.337(4) . ?
N3 C9 1.342(4) . ?
N3 C8 1.332(4) . ?
N7 C19 1.307(4) . ?
N7 C18 1.356(4) . ?
N1 C5 1.345(4) . ?
N1 C1 1.330(5) . ?
C10 C11 1.400(4) . ?
C10 C15 1.385(4) . ?
C6 C4 1.491(4) . ?
C6 C7 1.383(4) . ?
C14 C15 1.393(4) . ?
C14 C13 1.388(4) . ?
C4 C5 1.381(4) . ?
C4 C3 1.375(5) . ?
C11 C12 1.384(4) . ?
C11 C16 1.506(4) . ?
C15 H15 0.9300 . ?
N20 C18 1.352(5) . ?
N20 C21 1.504(6) . ?
N20 C23 1.494(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.382(4) . ?
C5 H5A 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.386(5) . ?
C8 H8 0.9300 . ?
C12 H12 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.377(5) . ?
C2 H2 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.440(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.338(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C25 H25 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
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
N5 H5 N1_$1 0.86 2.16 2.992(4) 162.9 2_666
N4 H4 N3_$2 0.86 2.27 3.068(4) 154.6 2_665
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
N2 C6 C4 C5 165.9(3) . . . . ?
N2 C6 C4 C3 -12.1(4) . . . . ?
N2 C6 C7 C8 -4.3(5) . . . . ?
N5 C14 C15 C10 -179.9(3) . . . . ?
N5 C14 C13 C12 -179.6(3) . . . . ?
N4 C10 C11 C12 177.9(3) . . . . ?
N4 C10 C11 C16 -2.4(5) . . . . ?
N4 C10 C15 C14 -178.9(3) . . . . ?
N1 C1 C2 C3 0.6(7) . . . . ?
C10 N4 C9 N2 -8.4(5) . . . . ?
C10 N4 C9 N3 174.1(3) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C6 N2 C9 N4 -175.5(3) . . . . ?
C6 N2 C9 N3 1.7(5) . . . . ?
C6 C4 C5 N1 -178.5(3) . . . . ?
C6 C4 C3 C2 179.5(3) . . . . ?
C6 C7 C8 N3 1.1(6) . . . . ?
C9 N2 C6 C4 -177.7(3) . . . . ?
C9 N2 C6 C7 3.0(5) . . . . ?
C9 N4 C10 C11 141.4(3) . . . . ?
C9 N4 C10 C15 -40.5(5) . . . . ?
C9 N3 C8 C7 3.1(6) . . . . ?
C14 N5 C17 N8 -174.6(3) . . . . ?
C14 N5 C17 N6 4.4(6) . . . . ?
C14 C13 C12 C11 0.2(6) . . . . ?
C4 C6 C7 C8 176.4(3) . . . . ?
C4 C3 C2 C1 -1.5(6) . . . . ?
C17 N5 C14 C15 175.6(3) . . . . ?
C17 N5 C14 C13 -5.9(6) . . . . ?
C17 N8 C19 Cl1 179.8(2) . . . . ?
C17 N8 C19 N7 -1.0(6) . . . . ?
C17 N6 C18 N7 0.3(6) . . . . ?
C17 N6 C18 N20 -179.8(4) . . . . ?
C11 C10 C15 C14 -0.9(5) . . . . ?
C15 C10 C11 C12 -0.1(5) . . . . ?
C15 C10 C11 C16 179.6(3) . . . . ?
C15 C14 C13 C12 -1.2(5) . . . . ?
C19 N8 C17 N5 -180.0(3) . . . . ?
C19 N8 C17 N6 1.0(5) . . . . ?
C19 N7 C18 N6 -0.2(6) . . . . ?
C19 N7 C18 N20 179.8(4) . . . . ?
C7 C6 C4 C5 -14.8(5) . . . . ?
C7 C6 C4 C3 167.2(3) . . . . ?
C13 C14 C15 C10 1.5(5) . . . . ?
C5 N1 C1 C2 0.4(6) . . . . ?
C5 C4 C3 C2 1.4(5) . . . . ?
C3 C4 C5 N1 -0.4(5) . . . . ?
C18 N6 C17 N5 -179.6(3) . . . . ?
C18 N6 C17 N8 -0.7(5) . . . . ?
C18 N7 C19 Cl1 179.9(3) . . . . ?
C18 N7 C19 N8 0.6(6) . . . . ?
C18 N20 C21 C22 -86.9(6) . . . . ?
C18 N20 C23 C24 -140.9(7) . . . . ?
C8 N3 C9 N2 -4.7(5) . . . . ?
C8 N3 C9 N4 172.6(3) . . . . ?
C1 N1 C5 C4 -0.5(6) . . . . ?
C16 C11 C12 C13 -179.3(4) . . . . ?
C21 N20 C18 N6 3.0(7) . . . . ?
C21 N20 C18 N7 -177.1(4) . . . . ?
C21 N20 C23 C24 48.4(9) . . . . ?
C23 N20 C18 N6 -167.6(5) . . . . ?
C23 N20 C18 N7 12.4(7) . . . . ?
C23 N20 C21 C22 83.7(6) . . . . ?
