#------------------------------------------------------------------------------
#$Date: 2022-08-31 12:01:24 +0300 (Wed, 31 Aug 2022) $
#$Revision: 277485 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105725.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_8105725
loop_
_publ_author_name
'Li, Zhang'
'Qiong, Wu'
'Jin, Tong-Yin'
'Zhang, Ya-Zhai'
'Wang, Xiao-Zhong'
'Zhang, Heng-Qiang'
_publ_section_title
;
 Crystal structure of
 (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one,
 C21H16I N3O2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              467
_journal_page_last               469
_journal_paper_doi               10.1515/ncrs-2022-0077
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C22 H18 I N3 O2'
_chemical_formula_sum            'C22 H18 I N3 O2'
_chemical_formula_weight         483.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 99.803(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7439(9)
_cell_length_b                   11.8391(8)
_cell_length_c                   13.4459(7)
_cell_measurement_reflns_used    2215
_cell_measurement_temperature    173(10)
_cell_measurement_theta_max      28.7150
_cell_measurement_theta_min      4.0770
_cell_volume                     1999.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2018/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(10)
_diffrn_detector_area_resol_mean 16.1213
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8887
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.442
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_description       block
_exptl_crystal_F_000             960.0
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.00088(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0365
_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)+(0.0355P)²+0.7986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2943
_reflns_number_total             3932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0077_suppl.cif
_cod_data_source_block           exp_5196
_cod_original_cell_volume        1999.1(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105725
_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.
;
loop_
_space_group_symop_operation_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_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
C1 C 0.3712(2) -0.0607(3) 0.7844(2) 0.0437(8) Uani 1 1 d . . . . .
C2 C 0.3524(3) -0.1590(3) 0.7297(3) 0.0652(11) Uani 1 1 d . . . . .
H2 H 0.318428 -0.156558 0.662833 0.078 Uiso 1 1 calc R U . . .
C3 C 0.3841(3) -0.2611(3) 0.7742(3) 0.0706(12) Uani 1 1 d . . . . .
H3 H 0.370880 -0.326692 0.736113 0.085 Uiso 1 1 calc R U . . .
C4 C 0.4343(3) -0.2696(3) 0.8726(3) 0.0534(9) Uani 1 1 d . . . . .
C5 C 0.4550(3) -0.1709(3) 0.9250(3) 0.0650(11) Uani 1 1 d . . . . .
H5 H 0.491487 -0.173180 0.991029 0.078 Uiso 1 1 calc R U . . .
C6 C 0.4229(3) -0.0676(3) 0.8822(3) 0.0609(10) Uani 1 1 d . . . . .
H6 H 0.436659 -0.002082 0.920330 0.073 Uiso 1 1 calc R U . . .
C7 C 0.4652(4) -0.3822(3) 0.9206(4) 0.0753(12) Uani 1 1 d . . . . .
H7A H 0.531208 -0.374794 0.966750 0.113 Uiso 1 1 calc R U . . .
H7B H 0.473561 -0.436138 0.869258 0.113 Uiso 1 1 calc R U . . .
H7C H 0.410636 -0.407447 0.956580 0.113 Uiso 1 1 calc R U . . .
C8 C 0.2741(3) 0.0711(3) 0.6529(2) 0.0474(8) Uani 1 1 d . . . . .
C9 C 0.2675(3) 0.1930(3) 0.6509(2) 0.0460(8) Uani 1 1 d . . . . .
C10 C 0.3288(3) 0.2287(3) 0.7452(3) 0.0488(8) Uani 1 1 d . . . . .
C11 C 0.3480(4) 0.3456(3) 0.7861(3) 0.0711(12) Uani 1 1 d . . . . .
H11A H 0.387369 0.342077 0.853535 0.107 Uiso 1 1 calc R U . . .
H11B H 0.280964 0.382373 0.786777 0.107 Uiso 1 1 calc R U . . .
H11C H 0.387952 0.387587 0.744141 0.107 Uiso 1 1 calc R U . . .
C12 C 0.2064(3) 0.2514(3) 0.5730(2) 0.0480(8) Uani 1 1 d . . . . .
C13 C 0.1963(3) 0.3744(3) 0.5742(3) 0.0508(9) Uani 1 1 d . U . . .
C14 C 0.1132(3) 0.4370(3) 0.5823(3) 0.0607(10) Uani 1 1 d . U . . .
H14 H 0.046827 0.410798 0.591899 0.073 Uiso 1 1 calc R U . . .
C15 C 0.1421(4) 0.5490(4) 0.5741(4) 0.0824(14) Uani 1 1 d . . . . .
H15 H 0.099557 0.611645 0.580225 0.099 Uiso 1 1 calc R U . . .
C16 C 0.2387(4) 0.5510(4) 0.5562(4) 0.0797(13) Uani 1 1 d . . . . .
H16 H 0.277347 0.615506 0.546490 0.096 Uiso 1 1 calc R U . . .
C17 C 0.0883(3) 0.2341(3) 0.4048(2) 0.0498(9) Uani 1 1 d . . . . .
C18 C 0.0001(3) 0.1723(3) 0.3628(3) 0.0554(9) Uani 1 1 d . . . . .
H18 H -0.017347 0.106851 0.394562 0.066 Uiso 1 1 calc R U . . .
C19 C -0.0627(3) 0.2069(3) 0.2738(3) 0.0545(9) Uani 1 1 d . . . . .
H19 H -0.121684 0.164630 0.245134 0.065 Uiso 1 1 calc R U . . .
C20 C -0.0368(3) 0.3046(3) 0.2281(2) 0.0484(8) Uani 1 1 d . . . . .
C21 C 0.0523(3) 0.3650(3) 0.2682(3) 0.0538(9) Uani 1 1 d . . . . .
H21 H 0.070007 0.429840 0.235710 0.065 Uiso 1 1 calc R U . . .
C22 C 0.1158(3) 0.3301(3) 0.3564(3) 0.0554(9) Uani 1 1 d . . . . .
H22 H 0.176583 0.370686 0.383087 0.066 Uiso 1 1 calc R U . . .
H3A H 0.151(3) 0.128(3) 0.500(3) 0.057(13) Uiso 1 1 d . . . . .
I1 I -0.13391(2) 0.36276(2) 0.09648(2) 0.06770(14) Uani 1 1 d . . . . .
N1 N 0.3383(2) 0.0463(2) 0.7428(2) 0.0460(7) Uani 1 1 d . . . . .
N2 N 0.3706(2) 0.1439(2) 0.7984(2) 0.0506(7) Uani 1 1 d . . . . .
N3 N 0.1503(3) 0.1940(3) 0.4959(2) 0.0607(9) Uani 1 1 d . . . . .
O1 O 0.2290(2) 0.0018(2) 0.59017(18) 0.0671(7) Uani 1 1 d . . . . .
O3 O 0.2754(2) 0.4394(3) 0.5540(3) 0.0889(9) Uani 1 1 d . . . . .
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'
I I -0.4742 1.8119 '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
C6 C1 C2 118.3(3) . .
C6 C1 N1 119.6(3) . .
C2 C1 N1 122.1(3) . .
C1 C2 C3 119.9(3) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C4 C3 C2 122.5(4) . .
C4 C3 H3 118.7 . .
C2 C3 H3 118.7 . .
C5 C4 C3 116.8(3) . .
C5 C4 C7 121.5(3) . .
C3 C4 C7 121.7(4) . .
C4 C5 C6 121.6(3) . .
C4 C5 H5 119.2 . .
C6 C5 H5 119.2 . .
C1 C6 C5 120.8(3) . .
C1 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O1 C8 N1 126.4(3) . .
O1 C8 C9 128.8(3) . .
N1 C8 C9 104.7(3) . .
C12 C9 C10 132.4(3) . .
C12 C9 C8 122.6(3) . .
C10 C9 C8 104.9(3) . .
N2 C10 C9 111.8(3) . .
N2 C10 C11 119.3(3) . .
C9 C10 C11 128.9(3) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N3 C12 C9 119.4(3) . .
N3 C12 C13 118.5(3) . .
C9 C12 C13 122.0(3) . .
C14 C13 O3 109.9(3) . .
C14 C13 C12 129.6(4) . .
O3 C13 C12 120.1(3) . .
C13 C14 C15 107.7(4) . .
C13 C14 H14 126.1 . .
C15 C14 H14 126.1 . .
C16 C15 C14 107.8(4) . .
C16 C15 H15 126.1 . .
C14 C15 H15 126.1 . .
C15 C16 O3 108.5(4) . .
C15 C16 H16 125.7 . .
O3 C16 H16 125.7 . .
C18 C17 C22 119.8(3) . .
C18 C17 N3 118.1(3) . .
C22 C17 N3 122.1(3) . .
C17 C18 C19 120.5(3) . .
C17 C18 H18 119.7 . .
C19 C18 H18 119.7 . .
C20 C19 C18 119.2(3) . .
C20 C19 H19 120.4 . .
C18 C19 H19 120.4 . .
C21 C20 C19 120.6(3) . .
C21 C20 I1 119.4(3) . .
C19 C20 I1 120.1(3) . .
C20 C21 C22 120.4(3) . .
C20 C21 H21 119.8 . .
C22 C21 H21 119.8 . .
C21 C22 C17 119.4(3) . .
C21 C22 H22 120.3 . .
C17 C22 H22 120.3 . .
C8 N1 N2 111.8(3) . .
C8 N1 C1 129.1(3) . .
N2 N1 C1 119.1(2) . .
C10 N2 N1 106.8(3) . .
C12 N3 C17 130.0(3) . .
C12 N3 H3A 117(3) . .
C17 N3 H3A 113(3) . .
C13 O3 C16 105.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.369(4) .
C1 C2 1.376(5) .
C1 N1 1.419(4) .
C2 C3 1.378(5) .
C2 H2 0.9300 .
C3 C4 1.371(5) .
C3 H3 0.9300 .
C4 C5 1.368(5) .
C4 C7 1.504(5) .
C5 C6 1.382(5) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 O1 1.244(4) .
C8 N1 1.372(4) .
C8 C9 1.445(5) .
C9 C12 1.380(4) .
C9 C10 1.435(4) .
C10 N2 1.293(4) .
C10 C11 1.494(5) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 N3 1.339(4) .
C12 C13 1.463(5) .
C13 C14 1.312(5) .
C13 O3 1.332(5) .
C14 C15 1.386(6) .
C14 H14 0.9300 .
C15 C16 1.294(6) .
C15 H15 0.9300 .
C16 O3 1.403(5) .
C16 H16 0.9300 .
C17 C18 1.379(5) .
C17 C22 1.383(5) .
C17 N3 1.422(4) .
C18 C19 1.384(5) .
C18 H18 0.9300 .
C19 C20 1.375(5) .
C19 H19 0.9300 .
C20 C21 1.372(5) .
C20 I1 2.096(3) .
C21 C22 1.381(5) .
C21 H21 0.9300 .
C22 H22 0.9300 .
N1 N2 1.400(4) .
N3 H3A 0.78(4) .
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
_geom_hbond_publ_flag
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
C2 H2 O1 0.93 2.32 2.935(4) 123.1 . yes
C18 H18 I1 0.93 3.33 3.846(4) 117.3 4_566 yes
C22 H22 O3 0.93 2.56 3.321(5) 139.5 . yes
N3 H3A O1 0.78(4) 2.07(4) 2.712(4) 140(4) . yes
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
C6 C1 C2 C3 1.0(6) . . . .
N1 C1 C2 C3 -178.7(4) . . . .
C1 C2 C3 C4 0.1(7) . . . .
C2 C3 C4 C5 -1.9(6) . . . .
C2 C3 C4 C7 178.1(4) . . . .
C3 C4 C5 C6 2.5(6) . . . .
C7 C4 C5 C6 -177.4(4) . . . .
C2 C1 C6 C5 -0.3(6) . . . .
N1 C1 C6 C5 179.4(4) . . . .
C4 C5 C6 C1 -1.5(6) . . . .
O1 C8 C9 C12 -0.5(6) . . . .
N1 C8 C9 C12 -177.9(3) . . . .
O1 C8 C9 C10 175.8(4) . . . .
N1 C8 C9 C10 -1.6(3) . . . .
C12 C9 C10 N2 177.2(4) . . . .
C8 C9 C10 N2 1.4(4) . . . .
C12 C9 C10 C11 -2.5(7) . . . .
C8 C9 C10 C11 -178.3(4) . . . .
C10 C9 C12 N3 -174.8(4) . . . .
C8 C9 C12 N3 0.3(5) . . . .
C10 C9 C12 C13 1.9(6) . . . .
C8 C9 C12 C13 177.0(3) . . . .
N3 C12 C13 C14 65.1(6) . . . .
C9 C12 C13 C14 -111.6(5) . . . .
N3 C12 C13 O3 -106.7(4) . . . .
C9 C12 C13 O3 76.6(5) . . . .
O3 C13 C14 C15 -4.3(5) . . . .
C12 C13 C14 C15 -176.8(4) . . . .
C13 C14 C15 C16 3.2(6) . . . .
C14 C15 C16 O3 -0.9(6) . . . .
C22 C17 C18 C19 -1.6(5) . . . .
N3 C17 C18 C19 -179.5(3) . . . .
C17 C18 C19 C20 -0.7(6) . . . .
C18 C19 C20 C21 2.3(5) . . . .
C18 C19 C20 I1 -177.5(3) . . . .
C19 C20 C21 C22 -1.7(5) . . . .
I1 C20 C21 C22 178.2(3) . . . .
C20 C21 C22 C17 -0.7(5) . . . .
C18 C17 C22 C21 2.2(5) . . . .
N3 C17 C22 C21 -179.9(3) . . . .
O1 C8 N1 N2 -176.1(3) . . . .
C9 C8 N1 N2 1.3(4) . . . .
O1 C8 N1 C1 2.0(6) . . . .
C9 C8 N1 C1 179.5(3) . . . .
C6 C1 N1 C8 -170.4(3) . . . .
C2 C1 N1 C8 9.3(5) . . . .
C6 C1 N1 N2 7.6(5) . . . .
C2 C1 N1 N2 -172.7(3) . . . .
C9 C10 N2 N1 -0.6(4) . . . .
C11 C10 N2 N1 179.1(3) . . . .
C8 N1 N2 C10 -0.5(4) . . . .
C1 N1 N2 C10 -178.8(3) . . . .
C9 C12 N3 C17 -175.1(4) . . . .
C13 C12 N3 C17 8.1(6) . . . .
C18 C17 N3 C12 -148.1(4) . . . .
C22 C17 N3 C12 34.0(6) . . . .
C14 C13 O3 C16 3.8(5) . . . .
C12 C13 O3 C16 177.0(3) . . . .
C15 C16 O3 C13 -1.7(5) . . . .
