#------------------------------------------------------------------------------
#$Date: 2021-07-05 20:45:02 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/74/7707418.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_7707418
loop_
_publ_author_name
'Shimada, Shigeru'
'Yin, Shuang-Feng'
'Bao, Ming'
_publ_section_title
;
 A new C-anionic tripodal ligand
 2-{bis(benzothiazolyl)(methoxy)methyl}phenyl and its bismuth complexes.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7949
_journal_page_last               7954
_journal_paper_doi               10.1039/d1dt01071a
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C22 H15 Bi Cl2 N2 O S2'
_chemical_formula_sum            'C22 H15 Bi Cl2 N2 O S2'
_chemical_formula_weight         667.36
_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             2020-04-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-03-26 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                102.1600(10)
_cell_angle_beta                 92.451(2)
_cell_angle_gamma                106.506(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9561(2)
_cell_length_b                   10.6585(2)
_cell_length_c                   11.9387(2)
_cell_measurement_reflns_used    6414
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.6310
_cell_measurement_theta_min      1.7510
_cell_volume                     1061.75(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.31 183.92   0.30    9.99    --   28.00  73.62 -25.69  606
  2  ω      2.31 132.67   0.30    9.99    --   28.00  73.62  64.31  435
  3  ω      2.31  71.24   0.30    9.99    --   28.00  73.62 154.31  230
  4  ω      2.31  17.29   0.30    9.99    --   28.00  73.62 -25.69   50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103237000
_diffrn_orient_matrix_UB_12      -0.0144927000
_diffrn_orient_matrix_UB_13      -0.0610970000
_diffrn_orient_matrix_UB_21      0.0277167000
_diffrn_orient_matrix_UB_22      0.0697693000
_diffrn_orient_matrix_UB_23      0.0017659000
_diffrn_orient_matrix_UB_31      0.0776597000
_diffrn_orient_matrix_UB_32      -0.0039072000
_diffrn_orient_matrix_UB_33      -0.0015893000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6322
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         1.755
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_description       needle
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method 'Crystallized from THF-d8'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0163
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0241P)²+1.3203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0401
_refine_ls_wR_factor_ref         0.0404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4158
_reflns_number_total             4255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01071a2.cif
_cod_data_source_block           LBiCl2
_cod_depositor_comments
'Adding full bibliography for 7707417--7707423.cif.'
_cod_database_code               7707418
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H15 Bi1 Cl2 N2 O1 S1'
_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   0.668
_shelx_estimated_absorpt_t_min   0.260
_reflns_odcompleteness_completeness 98.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.794
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
Bi1 Bi 0.50806(2) 0.30481(2) 0.81295(2) 0.01427(4) Uani 1 1 d . . . . .
Cl1 Cl 0.23390(8) 0.13818(7) 0.80679(6) 0.02305(14) Uani 1 1 d . . . . .
Cl2 Cl 0.43141(10) 0.52184(7) 0.85784(7) 0.02674(16) Uani 1 1 d . . . . .
S1 S 0.88581(8) 0.09304(7) 0.65694(6) 0.02007(14) Uani 1 1 d . . . . .
S2 S 1.02097(8) 0.48621(7) 0.65302(6) 0.01975(14) Uani 1 1 d . . . . .
O1 O 0.8359(2) 0.25680(19) 0.49464(17) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.6145(3) 0.1124(2) 0.7062(2) 0.0155(5) Uani 1 1 d . . . . .
N2 N 0.7898(3) 0.4307(2) 0.7738(2) 0.0159(5) Uani 1 1 d . . . . .
C1 C 0.4712(3) 0.2984(3) 0.6249(2) 0.0167(5) Uani 1 1 d . . . . .
C2 C 0.3311(4) 0.3157(3) 0.5860(3) 0.0217(6) Uani 1 1 d . . . . .
H2 H 0.252031 0.317919 0.636284 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3062(4) 0.3296(3) 0.4744(3) 0.0258(7) Uani 1 1 d . . . . .
H3 H 0.209693 0.339736 0.448091 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4214(4) 0.3287(3) 0.4019(3) 0.0253(6) Uani 1 1 d . . . . .
H4 H 0.406528 0.342399 0.326678 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5583(4) 0.3079(3) 0.4388(2) 0.0211(6) Uani 1 1 d . . . . .
H5 H 0.636830 0.306337 0.387927 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5840(3) 0.2890(3) 0.5495(2) 0.0155(5) Uani 1 1 d . . . . .
C7 C 0.7413(3) 0.2689(3) 0.5854(2) 0.0145(5) Uani 1 1 d . . . . .
C8 C 0.7269(3) 0.1537(3) 0.6457(2) 0.0150(5) Uani 1 1 d . . . . .
C9 C 0.7930(3) 0.0019(3) 0.7519(2) 0.0177(5) Uani 1 1 d . . . . .
C10 C 0.8456(4) -0.0791(3) 0.8116(3) 0.0244(6) Uani 1 1 d . . . . .
H10 H 0.944952 -0.092929 0.802294 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7490(4) -0.1385(3) 0.8845(3) 0.0267(7) Uani 1 1 d . . . . .
H11 H 0.782973 -0.193323 0.926949 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6016(4) -0.1198(3) 0.8974(3) 0.0231(6) Uani 1 1 d . . . . .
H12 H 0.536726 -0.163473 0.947367 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5492(3) -0.0396(3) 0.8392(2) 0.0192(6) Uani 1 1 d . . . . .
H13 H 0.449132 -0.027061 0.848251 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6471(3) 0.0229(3) 0.7666(2) 0.0157(5) Uani 1 1 d . . . . .
C15 C 0.8377(3) 0.3936(3) 0.6748(2) 0.0148(5) Uani 1 1 d . . . . .
C16 C 1.0377(3) 0.5861(3) 0.7911(2) 0.0172(5) Uani 1 1 d . . . . .
C17 C 1.1626(3) 0.6944(3) 0.8491(3) 0.0223(6) Uani 1 1 d . . . . .
H17 H 1.254386 0.725528 0.813302 0.027 Uiso 1 1 calc R U . . .
C18 C 1.1487(4) 0.7551(3) 0.9606(3) 0.0259(7) Uani 1 1 d . . . . .
H18 H 1.231701 0.830261 1.001939 0.031 Uiso 1 1 calc R U . . .
C19 C 1.0157(4) 0.7084(3) 1.0134(3) 0.0234(6) Uani 1 1 d . . . . .
H19 H 1.010645 0.751451 1.090764 0.028 Uiso 1 1 calc R U . . .
C20 C 0.8903(4) 0.6010(3) 0.9566(2) 0.0208(6) Uani 1 1 d . . . . .
H20 H 0.799453 0.569800 0.993217 0.025 Uiso 1 1 calc R U . . .
C21 C 0.9024(3) 0.5403(3) 0.8435(2) 0.0160(5) Uani 1 1 d . . . . .
C22 C 0.7870(4) 0.1325(3) 0.4073(2) 0.0246(6) Uani 1 1 d . . . . .
H22A H 0.801963 0.151960 0.331210 0.037 Uiso 1 1 calc R U . . .
H22B H 0.676114 0.086672 0.410031 0.037 Uiso 1 1 calc R U . . .
H22C H 0.849896 0.074558 0.421428 0.037 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'
Bi Bi -4.1077 10.2566 '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'
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
Cl1 Bi1 N1 91.65(5) . . ?
Cl1 Bi1 N2 165.91(5) . . ?
Cl2 Bi1 Cl1 97.90(2) . . ?
Cl2 Bi1 N1 160.84(5) . . ?
Cl2 Bi1 N2 92.31(5) . . ?
N2 Bi1 N1 75.87(7) . . ?
C1 Bi1 Cl1 91.94(7) . . ?
C1 Bi1 Cl2 88.87(7) . . ?
C1 Bi1 N1 74.17(9) . . ?
C1 Bi1 N2 78.52(9) . . ?
C9 S1 C8 89.14(13) . . ?
C15 S2 C16 88.66(13) . . ?
C7 O1 C22 116.8(2) . . ?
C8 N1 Bi1 113.24(17) . . ?
C8 N1 C14 110.9(2) . . ?
C14 N1 Bi1 119.28(17) . . ?
C15 N2 Bi1 119.26(17) . . ?
C15 N2 C21 111.1(2) . . ?
C21 N2 Bi1 129.65(18) . . ?
C2 C1 Bi1 116.5(2) . . ?
C6 C1 Bi1 123.7(2) . . ?
C6 C1 C2 119.6(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 122.9(2) . . ?
C5 C6 C7 118.3(2) . . ?
O1 C7 C6 113.7(2) . . ?
O1 C7 C8 109.9(2) . . ?
O1 C7 C15 104.9(2) . . ?
C8 C7 C6 114.5(2) . . ?
C15 C7 C6 108.8(2) . . ?
C15 C7 C8 104.2(2) . . ?
N1 C8 S1 116.1(2) . . ?
N1 C8 C7 124.2(2) . . ?
C7 C8 S1 118.6(2) . . ?
C10 C9 S1 129.5(2) . . ?
C10 C9 C14 120.9(3) . . ?
C14 C9 S1 109.6(2) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.0(3) . . ?
C14 C13 H13 121.0 . . ?
N1 C14 C9 114.3(2) . . ?
C13 C14 N1 125.0(3) . . ?
C13 C14 C9 120.7(3) . . ?
N2 C15 S2 116.6(2) . . ?
N2 C15 C7 121.7(2) . . ?
C7 C15 S2 121.6(2) . . ?
C17 C16 S2 128.7(2) . . ?
C17 C16 C21 121.3(3) . . ?
C21 C16 S2 109.9(2) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121.2 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.3(3) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.8(3) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 121.3 . . ?
C19 C20 C21 117.4(3) . . ?
C21 C20 H20 121.3 . . ?
N2 C21 C16 113.8(2) . . ?
N2 C21 C20 125.5(3) . . ?
C20 C21 C16 120.7(3) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Bi1 Cl1 2.5768(7) . ?
Bi1 Cl2 2.5536(7) . ?
Bi1 N1 2.618(2) . ?
Bi1 N2 2.613(2) . ?
Bi1 C1 2.239(3) . ?
S1 C8 1.734(3) . ?
S1 C9 1.734(3) . ?
S2 C15 1.721(3) . ?
S2 C16 1.739(3) . ?
O1 C7 1.410(3) . ?
O1 C22 1.443(3) . ?
N1 C8 1.293(4) . ?
N1 C14 1.395(3) . ?
N2 C15 1.296(4) . ?
N2 C21 1.387(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(4) . ?
C6 C7 1.541(4) . ?
C7 C8 1.527(4) . ?
C7 C15 1.525(4) . ?
C9 C10 1.392(4) . ?
C9 C14 1.399(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(4) . ?
C16 C17 1.388(4) . ?
C16 C21 1.398(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
Bi1 N1 C8 S1 135.78(14) . . . . ?
Bi1 N1 C8 C7 -32.3(3) . . . . ?
Bi1 N1 C14 C9 -132.2(2) . . . . ?
Bi1 N1 C14 C13 45.9(3) . . . . ?
Bi1 N2 C15 S2 177.10(11) . . . . ?
Bi1 N2 C15 C7 -6.8(3) . . . . ?
Bi1 N2 C21 C16 -176.49(18) . . . . ?
Bi1 N2 C21 C20 5.2(4) . . . . ?
Bi1 C1 C2 C3 172.1(2) . . . . ?
Bi1 C1 C6 C5 -169.7(2) . . . . ?
Bi1 C1 C6 C7 5.8(4) . . . . ?
S1 C9 C10 C11 178.6(2) . . . . ?
S1 C9 C14 N1 -1.9(3) . . . . ?
S1 C9 C14 C13 180.0(2) . . . . ?
S2 C16 C17 C18 -178.1(2) . . . . ?
S2 C16 C21 N2 -1.0(3) . . . . ?
S2 C16 C21 C20 177.5(2) . . . . ?
O1 C7 C8 S1 34.3(3) . . . . ?
O1 C7 C8 N1 -157.9(2) . . . . ?
O1 C7 C15 S2 0.0(3) . . . . ?
O1 C7 C15 N2 -175.9(2) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C1 C6 C7 O1 177.7(2) . . . . ?
C1 C6 C7 C8 50.2(3) . . . . ?
C1 C6 C7 C15 -65.9(3) . . . . ?
C2 C1 C6 C5 5.0(4) . . . . ?
C2 C1 C6 C7 -179.5(2) . . . . ?
C2 C3 C4 C5 2.9(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C1 -3.2(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C5 C6 C7 O1 -6.8(3) . . . . ?
C5 C6 C7 C8 -134.3(3) . . . . ?
C5 C6 C7 C15 109.6(3) . . . . ?
C6 C1 C2 C3 -2.9(4) . . . . ?
C6 C7 C8 S1 163.68(18) . . . . ?
C6 C7 C8 N1 -28.5(4) . . . . ?
C6 C7 C15 S2 -122.0(2) . . . . ?
C6 C7 C15 N2 62.1(3) . . . . ?
C8 S1 C9 C10 -177.4(3) . . . . ?
C8 S1 C9 C14 0.9(2) . . . . ?
C8 N1 C14 C9 2.1(3) . . . . ?
C8 N1 C14 C13 -179.8(3) . . . . ?
C8 C7 C15 S2 115.5(2) . . . . ?
C8 C7 C15 N2 -60.4(3) . . . . ?
C9 S1 C8 N1 0.3(2) . . . . ?
C9 S1 C8 C7 169.1(2) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C10 C9 C14 N1 176.5(2) . . . . ?
C10 C9 C14 C13 -1.6(4) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 N1 -176.6(3) . . . . ?
C12 C13 C14 C9 1.3(4) . . . . ?
C14 N1 C8 S1 -1.4(3) . . . . ?
C14 N1 C8 C7 -169.5(2) . . . . ?
C14 C9 C10 C11 0.5(4) . . . . ?
C15 S2 C16 C17 178.9(3) . . . . ?
C15 S2 C16 C21 0.4(2) . . . . ?
C15 N2 C21 C16 1.1(3) . . . . ?
C15 N2 C21 C20 -177.2(3) . . . . ?
C15 C7 C8 S1 -77.6(2) . . . . ?
C15 C7 C8 N1 90.2(3) . . . . ?
C16 S2 C15 N2 0.2(2) . . . . ?
C16 S2 C15 C7 -175.9(2) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C17 C16 C21 N2 -179.5(3) . . . . ?
C17 C16 C21 C20 -1.1(4) . . . . ?
C17 C18 C19 C20 -1.2(5) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 N2 179.1(3) . . . . ?
C19 C20 C21 C16 0.9(4) . . . . ?
C21 N2 C15 S2 -0.8(3) . . . . ?
C21 N2 C15 C7 175.3(2) . . . . ?
C21 C16 C17 C18 0.2(4) . . . . ?
C22 O1 C7 C6 -72.9(3) . . . . ?
C22 O1 C7 C8 56.9(3) . . . . ?
C22 O1 C7 C15 168.4(2) . . . . ?
