#------------------------------------------------------------------------------
#$Date: 2021-07-05 20:45:02 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/74/7707420.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_7707420
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         'C44 H30 Bi Cl N4 O2 S4'
_chemical_formula_sum            'C44 H30 Bi Cl N4 O2 S4'
_chemical_formula_weight         1019.39
_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                110.088(2)
_cell_angle_beta                 104.112(2)
_cell_angle_gamma                107.625(2)
_cell_formula_units_Z            2
_cell_length_a                   12.3209(3)
_cell_length_b                   13.3170(3)
_cell_length_c                   14.6867(3)
_cell_measurement_reflns_used    9470
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.4790
_cell_measurement_theta_min      1.7970
_cell_volume                     1987.42(10)
_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 0.989
_diffrn_measured_fraction_theta_max 0.980
_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   14.99    --   28.00  73.62 -25.69  606
  2  ω      2.31 132.67   0.30   14.99    --   28.00  73.62  64.31  435
  3  ω      2.31  71.24   0.30   14.99    --   28.00  73.62 154.31  230
  4  ω      2.31  17.29   0.30   14.99    --   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      -0.0391476000
_diffrn_orient_matrix_UB_12      -0.0337869000
_diffrn_orient_matrix_UB_13      -0.0541384000
_diffrn_orient_matrix_UB_21      0.0525440000
_diffrn_orient_matrix_UB_22      0.0100141000
_diffrn_orient_matrix_UB_23      -0.0133664000
_diffrn_orient_matrix_UB_31      0.0020547000
_diffrn_orient_matrix_UB_32      -0.0517786000
_diffrn_orient_matrix_UB_33      0.0022631000
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12258
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         1.602
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88434
_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    1.703
_exptl_crystal_description       plate
_exptl_crystal_F_000             1004
_exptl_crystal_recrystallization_method 'crystallized from THF-d8.'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.740
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0350
_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)+(0.0326P)²+5.7098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0781
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7782
_reflns_number_total             8277
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01071a2.cif
_cod_data_source_block           L2BiCl
_cod_depositor_comments
'Adding full bibliography for 7707417--7707423.cif.'
_cod_original_cell_volume        1987.42(9)
_cod_database_code               7707420
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H30 Bi1 Cl1 N4 O2 S4'
_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   0.870
_shelx_estimated_absorpt_t_min   0.674
_reflns_odcompleteness_completeness 97.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.67
_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), C24(H24), C25(H25), C26(H26), C27(H27),
  C32(H32), C33(H33), C34(H34), C35(H35), C39(H39), C40(H40), C41(H41), C42(H42)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
;
_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 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.822
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 0.80825(2) 0.81416(2) 0.32642(2) 0.01682(5) Uani 1 1 d . . . . .
Cl1 Cl 1.03091(11) 0.91220(12) 0.34034(12) 0.0370(3) Uani 1 1 d . . . . .
S1 S 0.97563(11) 1.07294(12) 0.18095(10) 0.0303(3) Uani 1 1 d . . . . .
S2 S 0.59651(11) 1.11732(10) 0.17058(9) 0.0227(2) Uani 1 1 d . . . . .
S3 S 0.46190(10) 0.47714(10) 0.33049(9) 0.0226(2) Uani 1 1 d . . . . .
S4 S 0.87937(11) 0.54131(11) 0.53490(10) 0.0276(3) Uani 1 1 d . . . . .
O1 O 0.8272(3) 1.0119(3) 0.2983(2) 0.0193(6) Uani 1 1 d . . . . .
O2 O 0.8086(3) 0.7085(3) 0.4679(2) 0.0191(6) Uani 1 1 d . . . . .
N1 N 0.7819(3) 1.0944(3) 0.0893(3) 0.0216(8) Uani 1 1 d . . . . .
N2 N 0.5742(4) 0.9710(3) 0.2515(3) 0.0232(8) Uani 1 1 d . . . . .
N3 N 0.5899(3) 0.6482(3) 0.3016(3) 0.0177(7) Uani 1 1 d . . . . .
N4 N 0.6419(3) 0.4202(3) 0.4326(3) 0.0214(8) Uani 1 1 d . . . . .
C1 C 0.7103(4) 0.7752(4) 0.1561(3) 0.0172(8) Uani 1 1 d . . . . .
C2 C 0.6501(4) 0.6569(4) 0.0803(4) 0.0238(10) Uani 1 1 d . . . . .
H2 H 0.659814 0.598189 0.099973 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5769(4) 0.6229(4) -0.0224(4) 0.0262(10) Uani 1 1 d . . . . .
H3 H 0.538611 0.542105 -0.072644 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5597(5) 0.7066(4) -0.0516(4) 0.0285(11) Uani 1 1 d . . . . .
H4 H 0.508462 0.683819 -0.121728 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6177(4) 0.8243(4) 0.0221(4) 0.0243(10) Uani 1 1 d . . . . .
H5 H 0.606151 0.882254 0.002197 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6924(4) 0.8583(4) 0.1247(3) 0.0181(8) Uani 1 1 d . . . . .
C7 C 0.7487(4) 0.9919(4) 0.2001(3) 0.0166(8) Uani 1 1 d . . . . .
C8 C 0.8242(4) 1.0586(4) 0.1547(3) 0.0183(8) Uani 1 1 d . . . . .
C9 C 0.9841(4) 1.1356(4) 0.0957(4) 0.0256(10) Uani 1 1 d . . . . .
C10 C 1.0810(5) 1.1748(5) 0.0647(5) 0.0383(13) Uani 1 1 d . . . . .
H10 H 1.156961 1.170879 0.092432 0.046 Uiso 1 1 calc R U . . .
C11 C 1.0637(5) 1.2189(5) -0.0067(4) 0.0369(13) Uani 1 1 d . . . . .
H11 H 1.129282 1.247553 -0.027291 0.044 Uiso 1 1 calc R U . . .
C12 C 0.9519(5) 1.2224(5) -0.0495(4) 0.0334(12) Uani 1 1 d . . . . .
H12 H 0.941927 1.252573 -0.099391 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8551(5) 1.1825(5) -0.0202(4) 0.0324(11) Uani 1 1 d . . . . .
H13 H 0.778384 1.184054 -0.050247 0.039 Uiso 1 1 calc R U . . .
C14 C 0.8719(4) 1.1400(4) 0.0541(3) 0.0215(9) Uani 1 1 d . . . . .
C15 C 0.6400(4) 1.0216(4) 0.2099(3) 0.0183(8) Uani 1 1 d . . . . .
C16 C 0.4780(4) 1.0880(4) 0.2142(4) 0.0237(9) Uani 1 1 d . . . . .
C17 C 0.3871(5) 1.1317(5) 0.2125(4) 0.0303(11) Uani 1 1 d . . . . .
H17 H 0.384969 1.186577 0.185243 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3013(5) 1.0916(5) 0.2518(4) 0.0339(12) Uani 1 1 d . . . . .
H18 H 0.239539 1.120379 0.252221 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3028(5) 1.0101(5) 0.2910(4) 0.0353(12) Uani 1 1 d . . . . .
H19 H 0.241335 0.983659 0.316427 0.042 Uiso 1 1 calc R U . . .
C20 C 0.3913(5) 0.9674(5) 0.2936(4) 0.0307(11) Uani 1 1 d . . . . .
H20 H 0.392687 0.912766 0.321313 0.037 Uiso 1 1 calc R U . . .
C21 C 0.4796(4) 1.0067(4) 0.2540(4) 0.0232(9) Uani 1 1 d . . . . .
C22 C 0.8726(5) 1.1277(4) 0.3836(4) 0.0279(10) Uani 1 1 d . . . . .
H22A H 0.803412 1.139862 0.399418 0.042 Uiso 1 1 calc R U . . .
H22B H 0.912899 1.187389 0.363401 0.042 Uiso 1 1 calc R U . . .
H22C H 0.932343 1.134885 0.446020 0.042 Uiso 1 1 calc R U . . .
C23 C 0.8254(4) 0.6391(4) 0.2726(4) 0.0206(9) Uani 1 1 d . . . . .
C24 C 0.8726(4) 0.6080(5) 0.1956(4) 0.0267(10) Uani 1 1 d . . . . .
H24 H 0.907601 0.664406 0.173123 0.032 Uiso 1 1 calc R U . . .
C25 C 0.8700(5) 0.4972(5) 0.1510(4) 0.0326(11) Uani 1 1 d . . . . .
H25 H 0.900846 0.477407 0.097180 0.039 Uiso 1 1 calc R U . . .
C26 C 0.8221(5) 0.4149(5) 0.1848(4) 0.0312(11) Uani 1 1 d . . . . .
H26 H 0.819561 0.338266 0.154184 0.037 Uiso 1 1 calc R U . . .
C27 C 0.7780(4) 0.4453(4) 0.2635(4) 0.0255(10) Uani 1 1 d . . . . .
H27 H 0.746058 0.389469 0.287522 0.031 Uiso 1 1 calc R U . . .
C28 C 0.7800(4) 0.5566(4) 0.3079(3) 0.0170(8) Uani 1 1 d . . . . .
C29 C 0.7290(4) 0.5879(4) 0.3946(3) 0.0178(8) Uani 1 1 d . . . . .
C30 C 0.5995(4) 0.5778(4) 0.3424(3) 0.0166(8) Uani 1 1 d . . . . .
C31 C 0.3829(4) 0.5341(4) 0.2622(4) 0.0225(9) Uani 1 1 d . . . . .
C32 C 0.2557(4) 0.4976(5) 0.2166(4) 0.0302(11) Uani 1 1 d . . . . .
H32 H 0.199048 0.436347 0.223093 0.036 Uiso 1 1 calc R U . . .
C33 C 0.2156(5) 0.5532(5) 0.1620(5) 0.0371(13) Uani 1 1 d . . . . .
H33 H 0.129306 0.528934 0.128900 0.045 Uiso 1 1 calc R U . . .
C34 C 0.2982(5) 0.6446(5) 0.1538(4) 0.0346(12) Uani 1 1 d . . . . .
H34 H 0.267116 0.681708 0.115767 0.042 Uiso 1 1 calc R U . . .
C35 C 0.4239(4) 0.6823(4) 0.1999(4) 0.0256(10) Uani 1 1 d . . . . .
H35 H 0.479936 0.745378 0.194985 0.031 Uiso 1 1 calc R U . . .
C36 C 0.4667(4) 0.6249(4) 0.2541(3) 0.0208(9) Uani 1 1 d . . . . .
C37 C 0.7340(4) 0.5127(4) 0.4507(3) 0.0197(9) Uani 1 1 d . . . . .
C38 C 0.8096(5) 0.4144(4) 0.5463(4) 0.0254(10) Uani 1 1 d . . . . .
C39 C 0.8641(5) 0.3637(5) 0.6016(4) 0.0314(11) Uani 1 1 d . . . . .
H39 H 0.950825 0.398685 0.640585 0.038 Uiso 1 1 calc R U . . .
C40 C 0.7877(5) 0.2612(5) 0.5976(4) 0.0330(12) Uani 1 1 d . . . . .
H40 H 0.822268 0.224300 0.633835 0.040 Uiso 1 1 calc R U . . .
C41 C 0.6610(5) 0.2109(5) 0.5415(4) 0.0334(12) Uani 1 1 d . . . . .
H41 H 0.610557 0.141257 0.541888 0.040 Uiso 1 1 calc R U . . .
C42 C 0.6060(5) 0.2586(4) 0.4853(4) 0.0287(11) Uani 1 1 d . . . . .
H42 H 0.519335 0.222083 0.445970 0.034 Uiso 1 1 calc R U . . .
C43 C 0.6819(4) 0.3627(4) 0.4880(3) 0.0208(9) Uani 1 1 d . . . . .
C44 C 0.7684(5) 0.7598(4) 0.5484(4) 0.0258(10) Uani 1 1 d . . . . .
H44A H 0.688340 0.759097 0.516197 0.039 Uiso 1 1 calc R U . . .
H44B H 0.829238 0.841442 0.595915 0.039 Uiso 1 1 calc R U . . .
H44C H 0.760091 0.714146 0.588314 0.039 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'
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'
Cl Cl 0.1484 0.1585 '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'
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 O1 73.82(7) . . ?
Cl1 Bi1 N3 161.36(8) . . ?
O1 Bi1 N3 123.80(10) . . ?
C1 Bi1 Cl1 96.82(11) . . ?
C1 Bi1 O1 65.70(12) . . ?
C1 Bi1 N3 86.70(13) . . ?
C23 Bi1 Cl1 87.43(11) . . ?
C23 Bi1 O1 147.70(13) . . ?
C23 Bi1 N3 74.15(13) . . ?
C23 Bi1 C1 91.48(15) . . ?
C9 S1 C8 88.6(2) . . ?
C16 S2 C15 88.8(2) . . ?
C30 S3 C31 88.7(2) . . ?
C38 S4 C37 88.5(2) . . ?
C7 O1 Bi1 116.2(2) . . ?
C7 O1 C22 116.0(3) . . ?
C22 O1 Bi1 123.6(3) . . ?
C29 O2 C44 115.0(3) . . ?
C8 N1 C14 110.4(4) . . ?
C15 N2 C21 110.0(4) . . ?
C30 N3 Bi1 116.5(3) . . ?
C30 N3 C36 111.1(4) . . ?
C36 N3 Bi1 132.4(3) . . ?
C37 N4 C43 110.2(4) . . ?
C2 C1 Bi1 117.3(3) . . ?
C6 C1 Bi1 124.8(3) . . ?
C6 C1 C2 117.4(4) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(4) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 123.5(4) . . ?
C5 C6 C1 120.9(4) . . ?
C5 C6 C7 115.5(4) . . ?
O1 C7 C6 108.1(3) . . ?
O1 C7 C8 109.3(3) . . ?
O1 C7 C15 110.6(3) . . ?
C8 C7 C6 108.1(3) . . ?
C8 C7 C15 114.0(3) . . ?
C15 C7 C6 106.5(3) . . ?
N1 C8 S1 116.7(3) . . ?
N1 C8 C7 125.1(4) . . ?
C7 C8 S1 117.8(3) . . ?
C10 C9 S1 129.5(4) . . ?
C14 C9 S1 109.6(3) . . ?
C14 C9 C10 120.9(5) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.4(5) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(5) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(5) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 N1 114.8(4) . . ?
C13 C14 N1 125.2(4) . . ?
C13 C14 C9 119.9(4) . . ?
N2 C15 S2 116.6(3) . . ?
N2 C15 C7 117.3(4) . . ?
C7 C15 S2 126.1(3) . . ?
C17 C16 S2 129.7(4) . . ?
C21 C16 S2 109.7(3) . . ?
C21 C16 C17 120.6(4) . . ?
C16 C17 H17 121.3 . . ?
C18 C17 C16 117.5(5) . . ?
C18 C17 H17 121.3 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.8(5) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.3(5) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 121.0 . . ?
C19 C20 C21 118.0(5) . . ?
C21 C20 H20 121.0 . . ?
N2 C21 C16 114.9(4) . . ?
N2 C21 C20 124.3(4) . . ?
C16 C21 C20 120.8(4) . . ?
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 . . ?
C24 C23 Bi1 119.7(3) . . ?
C24 C23 C28 118.0(4) . . ?
C28 C23 Bi1 122.0(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.7(5) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.8(5) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.4(5) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.8(4) . . ?
C28 C27 H27 119.6 . . ?
C23 C28 C29 120.0(4) . . ?
C27 C28 C23 120.2(4) . . ?
C27 C28 C29 119.8(4) . . ?
O2 C29 C28 106.1(3) . . ?
O2 C29 C30 109.0(3) . . ?
O2 C29 C37 108.7(3) . . ?
C30 C29 C28 107.1(3) . . ?
C37 C29 C28 110.7(3) . . ?
C37 C29 C30 114.8(3) . . ?
N3 C30 S3 116.1(3) . . ?
N3 C30 C29 118.1(4) . . ?
C29 C30 S3 125.7(3) . . ?
C32 C31 S3 128.5(4) . . ?
C32 C31 C36 121.6(4) . . ?
C36 C31 S3 109.8(3) . . ?
C31 C32 H32 121.3 . . ?
C33 C32 C31 117.5(5) . . ?
C33 C32 H32 121.3 . . ?
C32 C33 H33 119.2 . . ?
C32 C33 C34 121.6(5) . . ?
C34 C33 H33 119.2 . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.3(5) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 H35 121.0 . . ?
C34 C35 C36 118.0(5) . . ?
C36 C35 H35 121.0 . . ?
N3 C36 C31 114.2(4) . . ?
N3 C36 C35 125.7(4) . . ?
C31 C36 C35 120.0(4) . . ?
N4 C37 S4 116.8(3) . . ?
N4 C37 C29 125.1(4) . . ?
C29 C37 S4 117.6(3) . . ?
C39 C38 S4 128.9(4) . . ?
C39 C38 C43 121.6(5) . . ?
C43 C38 S4 109.5(3) . . ?
C38 C39 H39 121.2 . . ?
C40 C39 C38 117.5(5) . . ?
C40 C39 H39 121.2 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.1(5) . . ?
C41 C40 H40 119.4 . . ?
C40 C41 H41 119.0 . . ?
C42 C41 C40 122.1(5) . . ?
C42 C41 H41 119.0 . . ?
C41 C42 H42 121.1 . . ?
C41 C42 C43 117.9(5) . . ?
C43 C42 H42 121.1 . . ?
N4 C43 C38 114.9(4) . . ?
N4 C43 C42 125.2(4) . . ?
C42 C43 C38 119.8(4) . . ?
O2 C44 H44A 109.5 . . ?
O2 C44 H44B 109.5 . . ?
O2 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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 2.5781(11) . ?
Bi1 O1 2.753(3) . ?
Bi1 N3 2.761(4) . ?
Bi1 C1 2.289(4) . ?
Bi1 C23 2.284(4) . ?
S1 C8 1.746(4) . ?
S1 C9 1.733(5) . ?
S2 C15 1.736(4) . ?
S2 C16 1.725(5) . ?
S3 C30 1.738(4) . ?
S3 C31 1.738(5) . ?
S4 C37 1.751(4) . ?
S4 C38 1.735(5) . ?
O1 C7 1.410(5) . ?
O1 C22 1.439(5) . ?
O2 C29 1.430(5) . ?
O2 C44 1.431(5) . ?
N1 C8 1.282(6) . ?
N1 C14 1.398(6) . ?
N2 C15 1.295(6) . ?
N2 C21 1.389(6) . ?
N3 C30 1.292(5) . ?
N3 C36 1.392(6) . ?
N4 C37 1.287(6) . ?
N4 C43 1.396(5) . ?
C1 C2 1.399(6) . ?
C1 C6 1.391(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(6) . ?
C6 C7 1.548(6) . ?
C7 C8 1.519(6) . ?
C7 C15 1.532(6) . ?
C9 C10 1.398(7) . ?
C9 C14 1.396(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.371(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(6) . ?
C16 C17 1.408(6) . ?
C16 C21 1.398(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.373(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.404(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.391(6) . ?
C23 C28 1.397(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(6) . ?
C28 C29 1.540(6) . ?
C29 C30 1.534(6) . ?
C29 C37 1.505(6) . ?
C31 C32 1.394(6) . ?
C31 C36 1.395(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.368(8) . ?
C33 H33 0.9500 . ?
C33 C34 1.394(8) . ?
C34 H34 0.9500 . ?
C34 C35 1.377(7) . ?
C35 H35 0.9500 . ?
C35 C36 1.397(6) . ?
C38 C39 1.397(7) . ?
C38 C43 1.402(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.375(7) . ?
C40 H40 0.9500 . ?
C40 C41 1.388(8) . ?
C41 H41 0.9500 . ?
C41 C42 1.375(7) . ?
C42 H42 0.9500 . ?
C42 C43 1.399(6) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 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 O1 C7 C6 -12.5(4) . . . . ?
Bi1 O1 C7 C8 -130.0(3) . . . . ?
Bi1 O1 C7 C15 103.7(3) . . . . ?
Bi1 N3 C30 S3 177.79(18) . . . . ?
Bi1 N3 C30 C29 -3.5(5) . . . . ?
Bi1 N3 C36 C31 -177.7(3) . . . . ?
Bi1 N3 C36 C35 3.6(7) . . . . ?
Bi1 C1 C2 C3 172.7(3) . . . . ?
Bi1 C1 C6 C5 -171.1(3) . . . . ?
Bi1 C1 C6 C7 6.5(6) . . . . ?
Bi1 C23 C24 C25 -171.5(4) . . . . ?
Bi1 C23 C28 C27 171.8(3) . . . . ?
Bi1 C23 C28 C29 -6.7(6) . . . . ?
S1 C9 C10 C11 178.3(4) . . . . ?
S1 C9 C14 N1 -0.1(5) . . . . ?
S1 C9 C14 C13 -177.2(4) . . . . ?
S2 C16 C17 C18 179.1(4) . . . . ?
S2 C16 C21 N2 1.2(5) . . . . ?
S2 C16 C21 C20 -179.4(4) . . . . ?
S3 C31 C32 C33 -176.8(4) . . . . ?
S3 C31 C36 N3 -0.3(5) . . . . ?
S3 C31 C36 C35 178.5(4) . . . . ?
S4 C38 C39 C40 -179.6(4) . . . . ?
S4 C38 C43 N4 2.4(5) . . . . ?
S4 C38 C43 C42 179.9(4) . . . . ?
O1 C7 C8 S1 33.8(4) . . . . ?
O1 C7 C8 N1 -154.2(4) . . . . ?
O1 C7 C15 S2 126.0(3) . . . . ?
O1 C7 C15 N2 -53.9(5) . . . . ?
O2 C29 C30 S3 -130.2(3) . . . . ?
O2 C29 C30 N3 51.2(5) . . . . ?
O2 C29 C37 S4 -44.4(4) . . . . ?
O2 C29 C37 N4 144.2(4) . . . . ?
C1 C2 C3 C4 -1.4(7) . . . . ?
C1 C6 C7 O1 5.7(5) . . . . ?
C1 C6 C7 C8 123.9(4) . . . . ?
C1 C6 C7 C15 -113.2(4) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
C2 C1 C6 C7 177.7(4) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C5 C6 C1 -0.4(7) . . . . ?
C4 C5 C6 C7 -178.3(4) . . . . ?
C5 C6 C7 O1 -176.6(4) . . . . ?
C5 C6 C7 C8 -58.3(5) . . . . ?
C5 C6 C7 C15 64.5(5) . . . . ?
C6 C1 C2 C3 0.8(6) . . . . ?
C6 C7 C8 S1 -83.6(4) . . . . ?
C6 C7 C8 N1 88.4(5) . . . . ?
C6 C7 C15 S2 -116.8(4) . . . . ?
C6 C7 C15 N2 63.3(5) . . . . ?
C8 S1 C9 C10 -178.1(5) . . . . ?
C8 S1 C9 C14 -0.3(4) . . . . ?
C8 N1 C14 C9 0.7(6) . . . . ?
C8 N1 C14 C13 177.6(5) . . . . ?
C8 C7 C15 S2 2.3(5) . . . . ?
C8 C7 C15 N2 -177.6(4) . . . . ?
C9 S1 C8 N1 0.7(4) . . . . ?
C9 S1 C8 C7 173.4(3) . . . . ?
C9 C10 C11 C12 -1.5(9) . . . . ?
C10 C9 C14 N1 177.9(5) . . . . ?
C10 C9 C14 C13 0.8(8) . . . . ?
C10 C11 C12 C13 0.7(9) . . . . ?
C11 C12 C13 C14 0.8(8) . . . . ?
C12 C13 C14 N1 -178.3(5) . . . . ?
C12 C13 C14 C9 -1.6(8) . . . . ?
C14 N1 C8 S1 -0.9(5) . . . . ?
C14 N1 C8 C7 -173.0(4) . . . . ?
C14 C9 C10 C11 0.7(8) . . . . ?
C15 S2 C16 C17 -179.6(5) . . . . ?
C15 S2 C16 C21 -0.8(4) . . . . ?
C15 N2 C21 C16 -1.1(6) . . . . ?
C15 N2 C21 C20 179.5(5) . . . . ?
C15 C7 C8 S1 158.3(3) . . . . ?
C15 C7 C8 N1 -29.7(6) . . . . ?
C16 S2 C15 N2 0.2(4) . . . . ?
C16 S2 C15 C7 -179.7(4) . . . . ?
C16 C17 C18 C19 -0.7(8) . . . . ?
C17 C16 C21 N2 -179.8(4) . . . . ?
C17 C16 C21 C20 -0.4(7) . . . . ?
C17 C18 C19 C20 1.0(9) . . . . ?
C18 C19 C20 C21 -1.0(8) . . . . ?
C19 C20 C21 N2 -180.0(5) . . . . ?
C19 C20 C21 C16 0.7(7) . . . . ?
C21 N2 C15 S2 0.5(5) . . . . ?
C21 N2 C15 C7 -179.7(4) . . . . ?
C21 C16 C17 C18 0.4(7) . . . . ?
C22 O1 C7 C6 -170.4(3) . . . . ?
C22 O1 C7 C8 72.2(4) . . . . ?
C22 O1 C7 C15 -54.2(5) . . . . ?
C23 C24 C25 C26 -1.6(8) . . . . ?
C23 C28 C29 O2 -39.1(5) . . . . ?
C23 C28 C29 C30 77.2(5) . . . . ?
C23 C28 C29 C37 -156.9(4) . . . . ?
C24 C23 C28 C27 -2.6(7) . . . . ?
C24 C23 C28 C29 178.9(4) . . . . ?
C24 C25 C26 C27 -0.3(8) . . . . ?
C25 C26 C27 C28 0.7(8) . . . . ?
C26 C27 C28 C23 0.8(7) . . . . ?
C26 C27 C28 C29 179.3(4) . . . . ?
C27 C28 C29 O2 142.3(4) . . . . ?
C27 C28 C29 C30 -101.3(5) . . . . ?
C27 C28 C29 C37 24.6(6) . . . . ?
C28 C23 C24 C25 3.1(7) . . . . ?
C28 C29 C30 S3 115.5(4) . . . . ?
C28 C29 C30 N3 -63.1(5) . . . . ?
C28 C29 C37 S4 71.7(4) . . . . ?
C28 C29 C37 N4 -99.7(5) . . . . ?
C30 S3 C31 C32 177.6(5) . . . . ?
C30 S3 C31 C36 -0.2(3) . . . . ?
C30 N3 C36 C31 0.8(5) . . . . ?
C30 N3 C36 C35 -177.8(4) . . . . ?
C30 C29 C37 S4 -166.8(3) . . . . ?
C30 C29 C37 N4 21.7(6) . . . . ?
C31 S3 C30 N3 0.7(4) . . . . ?
C31 S3 C30 C29 -177.9(4) . . . . ?
C31 C32 C33 C34 -1.3(8) . . . . ?
C32 C31 C36 N3 -178.3(4) . . . . ?
C32 C31 C36 C35 0.5(7) . . . . ?
C32 C33 C34 C35 0.4(9) . . . . ?
C33 C34 C35 C36 0.9(8) . . . . ?
C34 C35 C36 N3 177.3(4) . . . . ?
C34 C35 C36 C31 -1.3(7) . . . . ?
C36 N3 C30 S3 -1.0(5) . . . . ?
C36 N3 C30 C29 177.7(4) . . . . ?
C36 C31 C32 C33 0.8(7) . . . . ?
C37 S4 C38 C39 177.5(5) . . . . ?
C37 S4 C38 C43 -1.7(4) . . . . ?
C37 N4 C43 C38 -1.9(6) . . . . ?
C37 N4 C43 C42 -179.2(4) . . . . ?
C37 C29 C30 S3 -7.9(5) . . . . ?
C37 C29 C30 N3 173.5(4) . . . . ?
C38 S4 C37 N4 0.7(4) . . . . ?
C38 S4 C37 C29 -171.5(4) . . . . ?
C38 C39 C40 C41 -0.7(8) . . . . ?
C39 C38 C43 N4 -176.8(4) . . . . ?
C39 C38 C43 C42 0.6(7) . . . . ?
C39 C40 C41 C42 1.7(8) . . . . ?
C40 C41 C42 C43 -1.5(8) . . . . ?
C41 C42 C43 N4 177.5(4) . . . . ?
C41 C42 C43 C38 0.3(7) . . . . ?
C43 N4 C37 S4 0.5(5) . . . . ?
C43 N4 C37 C29 172.1(4) . . . . ?
C43 C38 C39 C40 -0.5(7) . . . . ?
C44 O2 C29 C28 172.6(3) . . . . ?
C44 O2 C29 C30 57.6(4) . . . . ?
C44 O2 C29 C37 -68.3(4) . . . . ?
