#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:58:40 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159979.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_7159979
loop_
_publ_author_name
'Lin, Bohong'
'Ruan, Yaoping'
'Hou, Qi'
'Yuan, Zhijun'
'Liang, Yunshi'
'Zhang, Jing'
_publ_section_title
;
 Regioselective 5-exo-dig (halo)cyclization of
 N-propargyloxycarbonyl guanidine derivatives under mild
 conditions.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5585
_journal_page_last               5590
_journal_paper_doi               10.1039/d4ob00579a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C11 H8 Cl3 N3 O2'
_chemical_formula_sum            'C11 H8 Cl3 N3 O2'
_chemical_formula_weight         320.55
_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     dual
_audit_creation_date             2022-04-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-24 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                91.8130(10)
_cell_angle_beta                 97.6170(10)
_cell_angle_gamma                102.8260(10)
_cell_formula_units_Z            4
_cell_length_a                   7.5748(3)
_cell_length_b                   12.5331(4)
_cell_length_c                   13.9255(5)
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      68.728
_cell_measurement_theta_min      3.152
_cell_volume                     1275.11(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20912
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.605
_diffrn_reflns_theta_min         1.478
_diffrn_source_current           2.86
_diffrn_source_power             0.19985679999999997
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1415 before and 0.0857 after correction.
The Ratio of minimum to maximum transmission is 0.5177.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0617P)²+0.8554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6291
_reflns_number_total             6864
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00579a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7159978--7159982.cif.'
_cod_database_code               7159979
_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 C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C22(H22), C11(H11), C18(H18)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N5(H5A,H5B), C15(H15A,H15B), C4(H4A,H4B)
;
_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
Cl2 Cl 0.82903(6) 1.02594(3) 0.12531(3) 0.03224(11) Uani 1 1 d . . . . .
Cl5 Cl 0.65633(6) 0.25601(3) 0.73311(3) 0.03134(11) Uani 1 1 d . . . . .
Cl6 Cl 0.68663(6) 0.09494(4) 0.56237(3) 0.03296(11) Uani 1 1 d . . . . .
Cl3 Cl 0.84136(7) 0.78121(4) 0.07261(3) 0.03634(12) Uani 1 1 d . . . . .
Cl4 Cl 0.63995(7) 0.16924(4) 0.94215(3) 0.03566(12) Uani 1 1 d . . . . .
Cl1 Cl 0.84799(7) 1.10156(3) 0.34352(3) 0.03370(11) Uani 1 1 d . . . . .
O2 O 0.74576(17) 0.48535(10) 0.67012(9) 0.0282(3) Uani 1 1 d . . . . .
O3 O 0.30297(18) -0.47543(11) 0.84385(12) 0.0395(3) Uani 1 1 d . . . . .
O1 O 0.50964(18) 0.55281(12) 0.61024(11) 0.0369(3) Uani 1 1 d . . . . .
O4 O 0.5409(2) -0.54690(11) 0.89442(12) 0.0386(3) Uani 1 1 d . . . . .
N3 N 0.79833(17) 0.61387(11) 0.56332(10) 0.0214(2) Uani 1 1 d . . . . .
N1 N 0.87094(19) 0.70854(11) 0.43005(10) 0.0248(3) Uani 1 1 d . . . . .
N6 N 0.60378(19) -0.37476(11) 0.85003(10) 0.0229(3) Uani 1 1 d . . . . .
N2 N 0.6027(2) 0.72097(14) 0.49554(12) 0.0320(3) Uani 1 1 d . . . . .
H2A H 0.570804 0.766845 0.453682 0.038 Uiso 1 1 calc R U . . .
H2B H 0.534373 0.698691 0.540687 0.038 Uiso 1 1 calc R U . . .
N4 N 0.7093(2) -0.20025(12) 0.80451(13) 0.0309(3) Uani 1 1 d . . . . .
N5 N 0.3987(2) -0.26029(13) 0.82063(15) 0.0398(4) Uani 1 1 d . . . . .
H5A H 0.371041 -0.197553 0.806197 0.048 Uiso 1 1 calc R U . . .
H5B H 0.313287 -0.315543 0.834090 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6711(2) -0.02303(14) 0.86312(13) 0.0278(3) Uani 1 1 d . . . . .
H7 H 0.667864 -0.048215 0.926629 0.033 Uiso 1 1 calc R U . . .
C22 C 0.8436(2) 0.75060(13) 0.26236(12) 0.0248(3) Uani 1 1 d . . . . .
H22 H 0.845086 0.676869 0.245202 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6685(2) 0.55154(13) 0.61341(12) 0.0243(3) Uani 1 1 d . . . . .
C20 C 0.8355(2) 0.93371(13) 0.21382(11) 0.0236(3) Uani 1 1 d . . . . .
C16 C 0.7571(2) 0.68463(12) 0.49049(11) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.5718(2) -0.27177(12) 0.82212(12) 0.0227(3) Uani 1 1 d . . . . .
C21 C 0.8379(2) 0.82490(13) 0.19095(12) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.6796(2) 0.05100(13) 0.67842(12) 0.0246(3) Uani 1 1 d . . . . .
C6 C 0.6864(2) -0.09375(13) 0.78700(13) 0.0257(3) Uani 1 1 d . . . . .
C19 C 0.8403(2) 0.96578(13) 0.31070(12) 0.0236(3) Uani 1 1 d . . . . .
C17 C 0.8471(2) 0.78371(13) 0.35919(12) 0.0228(3) Uani 1 1 d . . . . .
C14 C 0.9729(2) 0.59252(13) 0.59304(11) 0.0216(3) Uani 1 1 d . . . . .
C8 C 0.6608(2) 0.08385(13) 0.84644(12) 0.0258(3) Uani 1 1 d . . . . .
C9 C 0.6658(2) 0.12265(12) 0.75392(12) 0.0239(3) Uani 1 1 d . . . . .
C3 C 0.7787(2) -0.39728(13) 0.87684(12) 0.0239(3) Uani 1 1 d . . . . .
C15 C 1.1351(2) 0.64156(15) 0.57173(14) 0.0307(3) Uani 1 1 d . . . . .
H15A H 1.145788 0.700889 0.530454 0.037 Uiso 1 1 calc R U . . .
H15B H 1.240975 0.617454 0.597680 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6907(2) -0.05630(13) 0.69399(13) 0.0268(3) Uani 1 1 d . . . . .
H11 H 0.701204 -0.103858 0.641612 0.032 Uiso 1 1 calc R U . . .
C18 C 0.8452(2) 0.89260(13) 0.38330(12) 0.0248(3) Uani 1 1 d . . . . .
H18 H 0.847230 0.916362 0.448980 0.030 Uiso 1 1 calc R U . . .
C4 C 0.9443(2) -0.33691(15) 0.87504(15) 0.0330(4) Uani 1 1 d . . . . .
H4A H 0.959690 -0.264992 0.852814 0.040 Uiso 1 1 calc R U . . .
H4B H 1.048307 -0.365289 0.895977 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4664(2) -0.46594(14) 0.86076(14) 0.0294(3) Uani 1 1 d . . . . .
C12 C 0.9370(2) 0.50027(14) 0.65928(13) 0.0274(3) Uani 1 1 d . . . . .
H12A H 0.960823 0.432619 0.630261 0.033 Uiso 1 1 calc R U . . .
H12B H 1.015558 0.519609 0.722901 0.033 Uiso 1 1 calc R U . . .
C1 C 0.7369(3) -0.51119(15) 0.91211(15) 0.0336(4) Uani 1 1 d . . . . .
H1A H 0.794352 -0.560355 0.875941 0.040 Uiso 1 1 calc R U . . .
H1B H 0.782526 -0.510302 0.982188 0.040 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'
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
C13 O2 C12 110.15(13) . . ?
C2 O4 C1 110.37(14) . . ?
C13 N3 C16 123.94(13) . . ?
C13 N3 C14 110.26(13) . . ?
C14 N3 C16 125.75(13) . . ?
C16 N1 C17 120.59(14) . . ?
C3 N6 C5 125.20(13) . . ?
C2 N6 C5 124.26(14) . . ?
C2 N6 C3 110.42(13) . . ?
H2A N2 H2B 120.0 . . ?
C16 N2 H2A 120.0 . . ?
C16 N2 H2B 120.0 . . ?
C5 N4 C6 118.22(14) . . ?
H5A N5 H5B 120.0 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.17(16) . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C17 120.23(15) . . ?
C17 C22 H22 119.9 . . ?
O2 C13 N3 109.81(13) . . ?
O1 C13 O2 121.83(15) . . ?
O1 C13 N3 128.36(15) . . ?
C21 C20 Cl2 121.25(12) . . ?
C19 C20 Cl2 120.82(12) . . ?
C19 C20 C21 117.92(14) . . ?
N1 C16 N3 116.74(13) . . ?
N1 C16 N2 128.03(15) . . ?
N2 C16 N3 115.20(14) . . ?
N4 C5 N6 116.86(14) . . ?
N4 C5 N5 127.46(15) . . ?
N5 C5 N6 115.63(14) . . ?
C22 C21 Cl3 118.52(13) . . ?
C22 C21 C20 121.24(15) . . ?
C20 C21 Cl3 120.20(12) . . ?
C9 C10 Cl6 120.26(12) . . ?
C11 C10 Cl6 118.30(13) . . ?
C11 C10 C9 121.44(15) . . ?
C7 C6 N4 120.50(16) . . ?
C11 C6 N4 119.77(16) . . ?
C11 C6 C7 119.60(15) . . ?
C20 C19 Cl1 119.68(12) . . ?
C20 C19 C18 121.77(15) . . ?
C18 C19 Cl1 118.52(13) . . ?
C22 C17 N1 118.14(14) . . ?
C22 C17 C18 119.20(14) . . ?
C18 C17 N1 122.35(15) . . ?
N3 C14 C12 104.44(13) . . ?
C15 C14 N3 129.96(15) . . ?
C15 C14 C12 125.58(15) . . ?
C7 C8 Cl4 119.07(13) . . ?
C7 C8 C9 120.91(16) . . ?
C9 C8 Cl4 120.02(13) . . ?
C10 C9 Cl5 120.52(12) . . ?
C10 C9 C8 118.37(14) . . ?
C8 C9 Cl5 121.11(13) . . ?
N6 C3 C1 104.02(14) . . ?
C4 C3 N6 131.05(16) . . ?
C4 C3 C1 124.92(16) . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C10 C11 C6 119.52(16) . . ?
C10 C11 H11 120.2 . . ?
C6 C11 H11 120.2 . . ?
C19 C18 C17 119.64(15) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 H4B 120.0 . . ?
H4A C4 H4B 120.0 . . ?
O3 C2 O4 122.38(16) . . ?
O3 C2 N6 127.89(16) . . ?
O4 C2 N6 109.73(15) . . ?
O2 C12 C14 104.91(12) . . ?
O2 C12 H12A 110.8 . . ?
O2 C12 H12B 110.8 . . ?
C14 C12 H12A 110.8 . . ?
C14 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
O4 C1 C3 105.22(14) . . ?
O4 C1 H1A 110.7 . . ?
O4 C1 H1B 110.7 . . ?
C3 C1 H1A 110.7 . . ?
C3 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
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
Cl2 C20 1.7196(16) . ?
Cl5 C9 1.7208(16) . ?
Cl6 C10 1.7274(17) . ?
Cl3 C21 1.7253(16) . ?
Cl4 C8 1.7283(18) . ?
Cl1 C19 1.7343(16) . ?
O2 C13 1.3373(19) . ?
O2 C12 1.448(2) . ?
O3 C2 1.207(2) . ?
O1 C13 1.202(2) . ?
O4 C2 1.335(2) . ?
O4 C1 1.438(2) . ?
N3 C13 1.392(2) . ?
N3 C16 1.4173(19) . ?
N3 C14 1.4181(19) . ?
N1 C16 1.279(2) . ?
N1 C17 1.407(2) . ?
N6 C5 1.422(2) . ?
N6 C3 1.420(2) . ?
N6 C2 1.391(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C16 1.355(2) . ?
N4 C5 1.271(2) . ?
N4 C6 1.408(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C5 1.348(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.393(2) . ?
C7 C8 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.387(2) . ?
C22 C17 1.393(2) . ?
C20 C21 1.395(2) . ?
C20 C19 1.389(2) . ?
C10 C9 1.391(2) . ?
C10 C11 1.388(2) . ?
C6 C11 1.394(2) . ?
C19 C18 1.389(2) . ?
C17 C18 1.399(2) . ?
C14 C15 1.322(2) . ?
C14 C12 1.502(2) . ?
C8 C9 1.394(2) . ?
C3 C4 1.317(2) . ?
C3 C1 1.505(2) . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
C4 H4A 0.9500 . ?
C4 H4B 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
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
Cl2 C20 C21 Cl3 1.9(2) . . . . ?
Cl2 C20 C21 C22 179.85(13) . . . . ?
Cl2 C20 C19 Cl1 -2.3(2) . . . . ?
Cl2 C20 C19 C18 179.86(13) . . . . ?
Cl6 C10 C9 Cl5 -0.2(2) . . . . ?
Cl6 C10 C9 C8 -179.91(13) . . . . ?
Cl6 C10 C11 C6 179.63(13) . . . . ?
Cl4 C8 C9 Cl5 1.4(2) . . . . ?
Cl4 C8 C9 C10 -178.94(12) . . . . ?
Cl1 C19 C18 C17 -177.27(13) . . . . ?
N3 C14 C12 O2 -6.31(17) . . . . ?
N1 C17 C18 C19 173.31(15) . . . . ?
N6 C3 C1 O4 4.73(19) . . . . ?
N4 C6 C11 C10 -175.97(15) . . . . ?
C7 C6 C11 C10 -0.1(2) . . . . ?
C7 C8 C9 Cl5 -179.04(13) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?
C13 O2 C12 C14 4.39(18) . . . . ?
C13 N3 C16 N1 -158.05(16) . . . . ?
C13 N3 C16 N2 23.6(2) . . . . ?
C13 N3 C14 C15 -172.19(18) . . . . ?
C13 N3 C14 C12 6.26(17) . . . . ?
C20 C19 C18 C17 0.6(3) . . . . ?
C16 N3 C13 O2 173.87(14) . . . . ?
C16 N3 C13 O1 -6.4(3) . . . . ?
C16 N3 C14 C15 10.2(3) . . . . ?
C16 N3 C14 C12 -171.34(14) . . . . ?
C16 N1 C17 C22 -125.95(17) . . . . ?
C16 N1 C17 C18 60.5(2) . . . . ?
C5 N6 C3 C4 -6.3(3) . . . . ?
C5 N6 C3 C1 172.68(15) . . . . ?
C5 N6 C2 O3 4.4(3) . . . . ?
C5 N6 C2 O4 -175.40(15) . . . . ?
C5 N4 C6 C7 74.2(2) . . . . ?
C5 N4 C6 C11 -109.9(2) . . . . ?
C21 C22 C17 N1 -173.87(15) . . . . ?
C21 C22 C17 C18 -0.1(2) . . . . ?
C21 C20 C19 Cl1 177.09(12) . . . . ?
C21 C20 C19 C18 -0.8(2) . . . . ?
C6 N4 C5 N6 -173.23(15) . . . . ?
C6 N4 C5 N5 4.3(3) . . . . ?
C6 C7 C8 Cl4 179.45(13) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C19 C20 C21 Cl3 -177.44(12) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C17 N1 C16 N3 -175.92(14) . . . . ?
C17 N1 C16 N2 2.1(3) . . . . ?
C17 C22 C21 Cl3 177.90(13) . . . . ?
C17 C22 C21 C20 0.0(2) . . . . ?
C14 N3 C13 O2 -3.78(19) . . . . ?
C14 N3 C13 O1 175.93(18) . . . . ?
C14 N3 C16 N1 19.2(2) . . . . ?
C14 N3 C16 N2 -159.07(15) . . . . ?
C8 C7 C6 N4 175.73(16) . . . . ?
C8 C7 C6 C11 -0.1(3) . . . . ?
C9 C10 C11 C6 0.6(2) . . . . ?
C3 N6 C5 N4 12.2(2) . . . . ?
C3 N6 C5 N5 -165.65(16) . . . . ?
C3 N6 C2 O3 -179.39(19) . . . . ?
C3 N6 C2 O4 0.8(2) . . . . ?
C15 C14 C12 O2 172.24(16) . . . . ?
C11 C10 C9 Cl5 178.82(13) . . . . ?
C11 C10 C9 C8 -0.9(2) . . . . ?
C4 C3 C1 O4 -176.19(18) . . . . ?
C2 O4 C1 C3 -4.5(2) . . . . ?
C2 N6 C5 N4 -172.10(17) . . . . ?
C2 N6 C5 N5 10.0(2) . . . . ?
C2 N6 C3 C4 177.48(19) . . . . ?
C2 N6 C3 C1 -3.52(18) . . . . ?
C12 O2 C13 O1 179.66(17) . . . . ?
C12 O2 C13 N3 -0.60(19) . . . . ?
C1 O4 C2 O3 -177.33(19) . . . . ?
C1 O4 C2 N6 2.4(2) . . . . ?
