#------------------------------------------------------------------------------
#$Date: 2023-06-29 12:20:44 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284570 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/93/1569328.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_1569328
loop_
_publ_author_name
'Korzun, André'
'Crespi, Stefano'
'Golz, Christopher'
'Bismuto, Alessandro'
_publ_section_title
;
 Replacing the BO in BODIPY: unlocking the path to SBDIPY and BIDIPY
 chromophores.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6579
_journal_page_last               6584
_journal_paper_doi               10.1039/d3sc01493b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H25 Bi Cl2 N2'
_chemical_formula_sum            'C22 H25 Bi Cl2 N2'
_chemical_formula_weight         597.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-19
_audit_creation_method
;FinalCif V113 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.984(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7393(7)
_cell_length_b                   15.609(2)
_cell_length_c                   36.440(5)
_cell_measurement_reflns_used    4915
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.712
_cell_measurement_theta_min      2.243
_cell_volume                     4391.4(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2022.1-1'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Ag'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11478
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.725
_diffrn_reflns_theta_min         2.128
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.282
_exptl_absorpt_correction_T_max  0.025393
_exptl_absorpt_correction_T_min  0.005216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_description       plate
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.021
_refine_diff_density_max         1.906
_refine_diff_density_min         -3.563
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         11478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0464
_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)+(0.0337P)²+38.7502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10465
_reflns_number_total             11478
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
'The data was integrated as a 2-component twin.'
_twin_individual_id              2
_twin_individual_twin_matrix_11  -7e-05
_twin_individual_twin_matrix_12  -3e-05
_twin_individual_twin_matrix_13  0.99999
_twin_individual_twin_matrix_21  -1.0
_twin_individual_twin_matrix_22  0.00015
_twin_individual_twin_matrix_23  -0.00024
_twin_individual_twin_matrix_31  -0.00076
_twin_individual_twin_matrix_32  -0.99999
_twin_individual_twin_matrix_33  -0.66013
_cod_data_source_file            d3sc01493b2.cif
_cod_data_source_block           mo_1852_cg_0m_4
_cod_original_cell_volume        4391.5(10)
_cod_database_code               1569328
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7246(7)
 0.2754(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C11(H11), C18(H18), C25(H25), C31(H31), C33(H33), C40(H40)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,
 H23B,H23C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C),
 C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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_min   0.308
_shelx_estimated_absorpt_t_max   0.845
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Bi1 Bi 0.24123(4) 0.65800(2) 0.29095(2) 0.03404(7) Uani 1 1 d . . . . .
Cl1 Cl 0.5687(3) 0.60028(12) 0.30170(6) 0.0381(4) Uani 1 1 d . . . . .
Cl2 Cl -0.0529(3) 0.74951(12) 0.29054(6) 0.0411(4) Uani 1 1 d . . . . .
N1 N 0.2909(9) 0.7330(4) 0.34247(18) 0.0356(14) Uani 1 1 d . . . . .
N2 N 0.1672(10) 0.5608(4) 0.33139(19) 0.0370(15) Uani 1 1 d . . . . .
C1 C 0.4726(12) 0.8373(6) 0.3111(2) 0.0433(18) Uani 1 1 d . . . . .
H1A H 0.495451 0.898992 0.312675 0.065 Uiso 1 1 calc R U . . .
H1B H 0.408969 0.824239 0.287574 0.065 Uiso 1 1 calc R U . . .
H1C H 0.582593 0.806006 0.312818 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3680(11) 0.8112(5) 0.3416(2) 0.0384(17) Uani 1 1 d . . . . .
C3 C 0.3351(12) 0.8550(5) 0.3739(3) 0.0424(19) Uani 1 1 d . . . . .
H3 H 0.377569 0.910442 0.380499 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2312(11) 0.8051(5) 0.3947(2) 0.0381(17) Uani 1 1 d . . . . .
C5 C 0.2002(12) 0.7271(6) 0.3745(2) 0.0393(18) Uani 1 1 d . . . . .
C6 C 0.1068(11) 0.6545(5) 0.3841(2) 0.0368(16) Uani 1 1 d . . . . .
C7 C 0.0222(11) 0.6577(6) 0.4203(2) 0.0386(17) Uani 1 1 d . . . . .
C8 C -0.1496(12) 0.6857(5) 0.4212(2) 0.0413(18) Uani 1 1 d . . . . .
C9 C -0.2246(12) 0.6880(6) 0.4544(3) 0.045(2) Uani 1 1 d . . . . .
H9 H -0.339690 0.708971 0.454898 0.054 Uiso 1 1 calc R U . . .
C10 C -0.1396(13) 0.6613(6) 0.4869(2) 0.0436(18) Uani 1 1 d . . . . .
C11 C 0.0317(13) 0.6333(6) 0.4856(3) 0.047(2) Uani 1 1 d . . . . .
H11 H 0.093611 0.615897 0.507825 0.056 Uiso 1 1 calc R U . . .
C12 C 0.1139(13) 0.6301(6) 0.4530(3) 0.045(2) Uani 1 1 d . . . . .
C13 C 0.2970(13) 0.5976(7) 0.4520(3) 0.051(2) Uani 1 1 d . . . . .
H13A H 0.296144 0.541611 0.439910 0.077 Uiso 1 1 calc R U . . .
H13B H 0.348928 0.592100 0.477239 0.077 Uiso 1 1 calc R U . . .
H13C H 0.364919 0.638145 0.438383 0.077 Uiso 1 1 calc R U . . .
C14 C -0.2261(15) 0.6638(8) 0.5233(3) 0.056(2) Uani 1 1 d . . . . .
H14A H -0.144785 0.642890 0.543134 0.084 Uiso 1 1 calc R U . . .
H14B H -0.329445 0.627380 0.521598 0.084 Uiso 1 1 calc R U . . .
H14C H -0.259530 0.722871 0.528639 0.084 Uiso 1 1 calc R U . . .
C15 C -0.2511(13) 0.7127(7) 0.3855(3) 0.048(2) Uani 1 1 d . . . . .
H15A H -0.270205 0.662632 0.369522 0.072 Uiso 1 1 calc R U . . .
H15B H -0.185008 0.755957 0.372958 0.072 Uiso 1 1 calc R U . . .
H15C H -0.363001 0.736728 0.391277 0.072 Uiso 1 1 calc R U . . .
C16 C 0.0909(11) 0.5777(5) 0.3652(2) 0.0353(16) Uani 1 1 d . . . . .
C17 C 0.0175(12) 0.4957(6) 0.3755(3) 0.0425(19) Uani 1 1 d . . . . .
C18 C 0.0603(12) 0.4365(5) 0.3498(2) 0.0426(19) Uani 1 1 d . . . . .
H18 H 0.032045 0.377297 0.350180 0.051 Uiso 1 1 calc R U . . .
C19 C 0.1523(11) 0.4772(5) 0.3231(2) 0.0379(17) Uani 1 1 d . . . . .
C20 C 0.2265(12) 0.4391(5) 0.2900(2) 0.0415(18) Uani 1 1 d . . . . .
H20A H 0.148097 0.449989 0.268227 0.062 Uiso 1 1 calc R U . . .
H20B H 0.240541 0.377151 0.293499 0.062 Uiso 1 1 calc R U . . .
H20C H 0.339489 0.465112 0.286620 0.062 Uiso 1 1 calc R U . . .
C21 C -0.0919(13) 0.4745(6) 0.4072(3) 0.048(2) Uani 1 1 d . . . . .
H21A H -0.026296 0.487171 0.430522 0.072 Uiso 1 1 calc R U . . .
H21B H -0.122416 0.413571 0.406301 0.072 Uiso 1 1 calc R U . . .
H21C H -0.197896 0.509056 0.405209 0.072 Uiso 1 1 calc R U . . .
C22 C 0.1698(14) 0.8328(6) 0.4312(2) 0.050(2) Uani 1 1 d . . . . .
H22A H 0.210344 0.891131 0.436764 0.075 Uiso 1 1 calc R U . . .
H22B H 0.216187 0.793733 0.450508 0.075 Uiso 1 1 calc R U . . .
H22C H 0.042941 0.831483 0.430065 0.075 Uiso 1 1 calc R U . . .
Bi2 Bi 0.78724(4) 0.16567(2) 0.27359(2) 0.03348(7) Uani 1 1 d . . . . .
Cl3 Cl 1.1113(3) 0.22327(13) 0.28407(6) 0.0395(4) Uani 1 1 d . . . . .
Cl4 Cl 0.4951(3) 0.07282(13) 0.27175(6) 0.0413(4) Uani 1 1 d . . . . .
N3 N 0.7096(9) 0.2562(4) 0.31681(19) 0.0358(15) Uani 1 1 d . . . . .
N4 N 0.8474(9) 0.0846(4) 0.32288(18) 0.0354(14) Uani 1 1 d . . . . .
C23 C 0.7533(11) 0.3847(5) 0.2778(2) 0.0384(18) Uani 1 1 d . . . . .
H23A H 0.671837 0.375892 0.256297 0.058 Uiso 1 1 calc R U . . .
H23B H 0.866650 0.361110 0.272772 0.058 Uiso 1 1 calc R U . . .
H23C H 0.764777 0.446213 0.282840 0.058 Uiso 1 1 calc R U . . .
C24 C 0.6873(11) 0.3405(5) 0.3104(2) 0.0381(16) Uani 1 1 d . . . . .
C25 C 0.6012(12) 0.3764(5) 0.3392(2) 0.0412(18) Uani 1 1 d . . . . .
H25 H 0.571013 0.435137 0.341355 0.049 Uiso 1 1 calc R U . . .
C26 C 0.5674(12) 0.3131(5) 0.3637(2) 0.0403(18) Uani 1 1 d . . . . .
C27 C 0.6393(11) 0.2347(5) 0.3499(2) 0.0341(16) Uani 1 1 d . . . . .
C28 C 0.6589(11) 0.1543(5) 0.3673(2) 0.0375(17) Uani 1 1 d . . . . .
C29 C 0.5722(12) 0.1428(5) 0.4027(2) 0.0381(18) Uani 1 1 d . . . . .
C30 C 0.6673(12) 0.1596(6) 0.4364(2) 0.0417(18) Uani 1 1 d . . . . .
C31 C 0.5837(13) 0.1449(6) 0.4685(3) 0.046(2) Uani 1 1 d . . . . .
H31 H 0.643902 0.157246 0.491480 0.056 Uiso 1 1 calc R U . . .
C32 C 0.4166(14) 0.1132(6) 0.4682(3) 0.050(2) Uani 1 1 d . . . . .
C33 C 0.3282(13) 0.0989(6) 0.4342(3) 0.045(2) Uani 1 1 d . . . . .
H33 H 0.212581 0.078204 0.433395 0.054 Uiso 1 1 calc R U . . .
C34 C 0.4038(12) 0.1140(5) 0.4012(2) 0.0393(18) Uani 1 1 d . . . . .
C35 C 0.2996(12) 0.0995(6) 0.3649(3) 0.047(2) Uani 1 1 d . . . . .
H35A H 0.257304 0.154535 0.354989 0.070 Uiso 1 1 calc R U . . .
H35B H 0.200994 0.062003 0.368832 0.070 Uiso 1 1 calc R U . . .
H35C H 0.373404 0.072420 0.347409 0.070 Uiso 1 1 calc R U . . .
C36 C 0.3290(17) 0.0948(7) 0.5035(3) 0.065(3) Uani 1 1 d . . . . .
H36A H 0.307579 0.033163 0.505442 0.097 Uiso 1 1 calc R U . . .
H36B H 0.218733 0.125762 0.503114 0.097 Uiso 1 1 calc R U . . .
H36C H 0.404381 0.113709 0.524693 0.097 Uiso 1 1 calc R U . . .
C37 C 0.8464(15) 0.1941(7) 0.4376(3) 0.053(2) Uani 1 1 d . . . . .
H37A H 0.843117 0.254293 0.429954 0.080 Uiso 1 1 calc R U . . .
H37B H 0.914803 0.161022 0.420924 0.080 Uiso 1 1 calc R U . . .
H37C H 0.899594 0.189733 0.462737 0.080 Uiso 1 1 calc R U . . .
C38 C 0.7570(11) 0.0849(5) 0.3559(2) 0.0339(15) Uani 1 1 d . . . . .
C39 C 0.7929(11) 0.0033(5) 0.3734(2) 0.0369(17) Uani 1 1 d . . . . .
C40 C 0.8995(11) -0.0405(5) 0.3512(2) 0.0377(17) Uani 1 1 d . . . . .
H40 H 0.944190 -0.096352 0.356080 0.045 Uiso 1 1 calc R U . . .
C41 C 0.9324(11) 0.0090(5) 0.3205(2) 0.0368(17) Uani 1 1 d . . . . .
C42 C 1.0428(10) -0.0107(5) 0.2904(2) 0.0385(17) Uani 1 1 d . . . . .
H42A H 1.147834 0.024447 0.292893 0.058 Uiso 1 1 calc R U . . .
H42B H 0.979395 0.001670 0.266745 0.058 Uiso 1 1 calc R U . . .
H42C H 1.074737 -0.071485 0.291362 0.058 Uiso 1 1 calc R U . . .
C43 C 0.7419(13) -0.0302(6) 0.4098(3) 0.045(2) Uani 1 1 d . . . . .
H43A H 0.756124 -0.092628 0.410507 0.067 Uiso 1 1 calc R U . . .
H43B H 0.620622 -0.015730 0.412917 0.067 Uiso 1 1 calc R U . . .
H43C H 0.815850 -0.004263 0.429713 0.067 Uiso 1 1 calc R U . . .
C44 C 0.4716(13) 0.3280(6) 0.3978(3) 0.047(2) Uani 1 1 d . . . . .
H44A H 0.548077 0.314816 0.419664 0.071 Uiso 1 1 calc R U . . .
H44B H 0.369564 0.290702 0.397243 0.071 Uiso 1 1 calc R U . . .
H44C H 0.435014 0.387975 0.398688 0.071 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'
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
Cl2 Bi1 Cl1 165.31(6) . . ?
N1 Bi1 Cl1 86.98(19) . . ?
N1 Bi1 Cl2 79.72(19) . . ?
N2 Bi1 Cl1 87.6(2) . . ?
N2 Bi1 Cl2 96.3(2) . . ?
N2 Bi1 N1 80.6(3) . . ?
C2 N1 Bi1 120.3(6) . . ?
C2 N1 C5 108.8(7) . . ?
C5 N1 Bi1 126.8(6) . . ?
C16 N2 Bi1 126.1(5) . . ?
C19 N2 Bi1 122.5(6) . . ?
C19 N2 C16 109.9(7) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 121.9(8) . . ?
N1 C2 C3 108.4(8) . . ?
C3 C2 C1 129.7(8) . . ?
C2 C3 H3 125.4 . . ?
C4 C3 C2 109.3(8) . . ?
C4 C3 H3 125.4 . . ?
C3 C4 C5 106.3(8) . . ?
C3 C4 C22 123.5(8) . . ?
C5 C4 C22 130.2(8) . . ?
N1 C5 C4 107.2(7) . . ?
C6 C5 N1 123.9(8) . . ?
C6 C5 C4 128.9(8) . . ?
C5 C6 C7 117.0(7) . . ?
C16 C6 C5 127.1(8) . . ?
C16 C6 C7 115.8(8) . . ?
C8 C7 C6 119.8(8) . . ?
C8 C7 C12 120.0(8) . . ?
C12 C7 C6 120.2(8) . . ?
C7 C8 C15 119.9(8) . . ?
C9 C8 C7 119.0(8) . . ?
C9 C8 C15 121.0(9) . . ?
C8 C9 H9 118.6 . . ?
C8 C9 C10 122.7(9) . . ?
C10 C9 H9 118.6 . . ?
C9 C10 C11 117.6(8) . . ?
C9 C10 C14 121.8(9) . . ?
C11 C10 C14 120.6(9) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.0(9) . . ?
C12 C11 H11 119.0 . . ?
C7 C12 C13 120.2(9) . . ?
C11 C12 C7 118.6(9) . . ?
C11 C12 C13 121.3(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 104.6(7) . . ?
C6 C16 N2 124.3(7) . . ?
C6 C16 C17 130.7(8) . . ?
C16 C17 C21 129.5(8) . . ?
C18 C17 C16 107.3(8) . . ?
C18 C17 C21 123.2(8) . . ?
C17 C18 H18 125.4 . . ?
C17 C18 C19 109.2(8) . . ?
C19 C18 H18 125.4 . . ?
N2 C19 C18 108.9(8) . . ?
N2 C19 C20 122.4(8) . . ?
C18 C19 C20 128.6(8) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl3 Bi2 Cl4 165.56(6) . . ?
N3 Bi2 Cl3 88.96(19) . . ?
N3 Bi2 Cl4 95.29(19) . . ?
N4 Bi2 Cl3 86.23(19) . . ?
N4 Bi2 Cl4 80.85(19) . . ?
N4 Bi2 N3 80.9(3) . . ?
C24 N3 Bi2 122.4(6) . . ?
C24 N3 C27 109.3(7) . . ?
C27 N3 Bi2 126.7(5) . . ?
C38 N4 Bi2 126.2(5) . . ?
C41 N4 Bi2 121.3(5) . . ?
C41 N4 C38 108.8(7) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
N3 C24 C23 122.8(8) . . ?
N3 C24 C25 109.0(7) . . ?
C25 C24 C23 128.1(8) . . ?
C24 C25 H25 125.6 . . ?
C26 C25 C24 108.8(8) . . ?
C26 C25 H25 125.6 . . ?
C25 C26 C27 106.7(8) . . ?
C25 C26 C44 123.6(8) . . ?
C27 C26 C44 129.7(8) . . ?
N3 C27 C26 106.2(7) . . ?
N3 C27 C28 124.4(8) . . ?
C28 C27 C26 128.9(8) . . ?
C27 C28 C29 116.8(7) . . ?
C38 C28 C27 126.8(8) . . ?
C38 C28 C29 116.4(7) . . ?
C30 C29 C28 119.1(8) . . ?
C34 C29 C28 119.0(8) . . ?
C34 C29 C30 121.9(8) . . ?
C29 C30 C37 121.5(8) . . ?
C31 C30 C29 117.1(9) . . ?
C31 C30 C37 121.4(9) . . ?
C30 C31 H31 118.6 . . ?
C32 C31 C30 122.7(9) . . ?
C32 C31 H31 118.6 . . ?
C31 C32 C33 117.7(9) . . ?
C31 C32 C36 122.2(10) . . ?
C33 C32 C36 120.2(10) . . ?
C32 C33 H33 118.9 . . ?
C34 C33 C32 122.1(9) . . ?
C34 C33 H33 118.9 . . ?
C29 C34 C33 118.5(9) . . ?
C29 C34 C35 121.7(8) . . ?
C33 C34 C35 119.8(8) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C30 C37 H37A 109.5 . . ?
C30 C37 H37B 109.5 . . ?
C30 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N4 C38 C39 106.1(7) . . ?
C28 C38 N4 123.8(7) . . ?
C28 C38 C39 130.0(8) . . ?
C38 C39 C43 130.0(8) . . ?
C40 C39 C38 106.6(7) . . ?
C40 C39 C43 123.3(8) . . ?
C39 C40 H40 124.9 . . ?
C39 C40 C41 110.1(7) . . ?
C41 C40 H40 124.9 . . ?
N4 C41 C40 108.3(7) . . ?
N4 C41 C42 122.6(7) . . ?
C40 C41 C42 129.0(7) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C39 C43 H43A 109.5 . . ?
C39 C43 H43B 109.5 . . ?
C39 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C26 C44 H44A 109.5 . . ?
C26 C44 H44B 109.5 . . ?
C26 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 2.692(2) . ?
Bi1 Cl2 2.687(2) . ?
Bi1 N1 2.223(7) . ?
Bi1 N2 2.218(7) . ?
N1 C2 1.359(10) . ?
N1 C5 1.406(11) . ?
N2 C16 1.427(11) . ?
N2 C19 1.344(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.478(12) . ?
C2 C3 1.399(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(13) . ?
C4 C5 1.434(12) . ?
C4 C22 1.507(12) . ?
C5 C6 1.403(12) . ?
C6 C7 1.513(11) . ?
C6 C16 1.384(11) . ?
C7 C8 1.402(12) . ?
C7 C12 1.410(13) . ?
C8 C9 1.378(12) . ?
C8 C15 1.529(13) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(13) . ?
C10 C11 1.400(14) . ?
C10 C14 1.530(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(13) . ?
C12 C13 1.507(14) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.461(12) . ?
C17 C18 1.373(13) . ?
C17 C21 1.514(13) . ?
C18 H18 0.9500 . ?
C18 C19 1.398(12) . ?
C19 C20 1.494(12) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Bi2 Cl3 2.667(2) . ?
Bi2 Cl4 2.683(2) . ?
Bi2 N3 2.229(7) . ?
Bi2 N4 2.220(7) . ?
N3 C24 1.345(10) . ?
N3 C27 1.398(10) . ?
N4 C38 1.433(10) . ?
N4 C41 1.356(10) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C24 1.497(11) . ?
C24 C25 1.398(12) . ?
C25 H25 0.9500 . ?
C25 C26 1.370(12) . ?
C26 C27 1.449(11) . ?
C26 C44 1.507(12) . ?
C27 C28 1.410(11) . ?
C28 C29 1.504(12) . ?
C28 C38 1.402(11) . ?
C29 C30 1.412(12) . ?
C29 C34 1.376(12) . ?
C30 C31 1.394(12) . ?
C30 C37 1.485(14) . ?
C31 H31 0.9500 . ?
C31 C32 1.384(15) . ?
C32 C33 1.393(14) . ?
C32 C36 1.522(13) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(12) . ?
C34 C35 1.519(13) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.441(10) . ?
C39 C40 1.376(12) . ?
C39 C43 1.505(12) . ?
C40 H40 0.9500 . ?
C40 C41 1.397(11) . ?
C41 C42 1.471(11) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
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 N1 C2 C1 -20.8(10) . . . . ?
Bi1 N1 C2 C3 161.6(6) . . . . ?
Bi1 N1 C5 C4 -159.5(6) . . . . ?
Bi1 N1 C5 C6 23.5(11) . . . . ?
Bi1 N2 C16 C6 -24.1(11) . . . . ?
Bi1 N2 C16 C17 162.4(6) . . . . ?
Bi1 N2 C19 C18 -164.0(6) . . . . ?
Bi1 N2 C19 C20 16.1(12) . . . . ?
N1 C2 C3 C4 -2.1(10) . . . . ?
N1 C5 C6 C7 177.7(7) . . . . ?
N1 C5 C6 C16 1.7(14) . . . . ?
N2 C16 C17 C18 3.2(10) . . . . ?
N2 C16 C17 C21 -174.7(9) . . . . ?
C1 C2 C3 C4 -179.4(8) . . . . ?
C2 N1 C5 C4 -2.5(9) . . . . ?
C2 N1 C5 C6 -179.5(8) . . . . ?
C2 C3 C4 C5 0.5(10) . . . . ?
C2 C3 C4 C22 -179.7(8) . . . . ?
C3 C4 C5 N1 1.2(9) . . . . ?
C3 C4 C5 C6 178.0(9) . . . . ?
C4 C5 C6 C7 1.5(13) . . . . ?
C4 C5 C6 C16 -174.6(9) . . . . ?
C5 N1 C2 C1 -179.6(7) . . . . ?
C5 N1 C2 C3 2.9(9) . . . . ?
C5 C6 C7 C8 92.5(10) . . . . ?
C5 C6 C7 C12 -89.4(10) . . . . ?
C5 C6 C16 N2 -1.3(14) . . . . ?
C5 C6 C16 C17 170.5(9) . . . . ?
C6 C7 C8 C9 179.9(8) . . . . ?
C6 C7 C8 C15 0.1(12) . . . . ?
C6 C7 C12 C11 -179.5(8) . . . . ?
C6 C7 C12 C13 0.3(13) . . . . ?
C6 C16 C17 C18 -169.7(9) . . . . ?
C6 C16 C17 C21 12.3(16) . . . . ?
C7 C6 C16 N2 -177.4(7) . . . . ?
C7 C6 C16 C17 -5.6(13) . . . . ?
C7 C8 C9 C10 -2.2(14) . . . . ?
C8 C7 C12 C11 -1.4(13) . . . . ?
C8 C7 C12 C13 178.3(8) . . . . ?
C8 C9 C10 C11 2.0(14) . . . . ?
C8 C9 C10 C14 -179.5(9) . . . . ?
C9 C10 C11 C12 -1.5(14) . . . . ?
C10 C11 C12 C7 1.3(14) . . . . ?
C10 C11 C12 C13 -178.5(9) . . . . ?
C12 C7 C8 C9 1.9(13) . . . . ?
C12 C7 C8 C15 -177.9(8) . . . . ?
C14 C10 C11 C12 179.9(9) . . . . ?
C15 C8 C9 C10 177.6(9) . . . . ?
C16 N2 C19 C18 2.5(10) . . . . ?
C16 N2 C19 C20 -177.4(8) . . . . ?
C16 C6 C7 C8 -91.0(10) . . . . ?
C16 C6 C7 C12 87.1(10) . . . . ?
C16 C17 C18 C19 -1.9(11) . . . . ?
C17 C18 C19 N2 -0.3(11) . . . . ?
C17 C18 C19 C20 179.6(9) . . . . ?
C19 N2 C16 C6 170.1(8) . . . . ?
C19 N2 C16 C17 -3.5(9) . . . . ?
C21 C17 C18 C19 176.2(8) . . . . ?
C22 C4 C5 N1 -178.5(9) . . . . ?
C22 C4 C5 C6 -1.8(16) . . . . ?
Bi2 N3 C24 C23 -15.7(11) . . . . ?
Bi2 N3 C24 C25 166.3(6) . . . . ?
Bi2 N3 C27 C26 -164.8(6) . . . . ?
Bi2 N3 C27 C28 22.6(11) . . . . ?
Bi2 N4 C38 C28 -23.0(11) . . . . ?
Bi2 N4 C38 C39 158.2(6) . . . . ?
Bi2 N4 C41 C40 -159.6(6) . . . . ?
Bi2 N4 C41 C42 22.3(11) . . . . ?
N3 C24 C25 C26 -0.7(10) . . . . ?
N3 C27 C28 C29 -179.4(7) . . . . ?
N3 C27 C28 C38 3.5(14) . . . . ?
N4 C38 C39 C40 0.3(9) . . . . ?
N4 C38 C39 C43 175.9(8) . . . . ?
C23 C24 C25 C26 -178.6(8) . . . . ?
C24 N3 C27 C26 0.9(9) . . . . ?
C24 N3 C27 C28 -171.7(8) . . . . ?
C24 C25 C26 C27 1.2(10) . . . . ?
C24 C25 C26 C44 -178.3(8) . . . . ?
C25 C26 C27 N3 -1.3(10) . . . . ?
C25 C26 C27 C28 170.8(9) . . . . ?
C26 C27 C28 C29 9.7(13) . . . . ?
C26 C27 C28 C38 -167.4(9) . . . . ?
C27 N3 C24 C23 177.9(8) . . . . ?
C27 N3 C24 C25 -0.1(10) . . . . ?
C27 C28 C29 C30 -92.9(10) . . . . ?
C27 C28 C29 C34 88.8(10) . . . . ?
C27 C28 C38 N4 -3.3(14) . . . . ?
C27 C28 C38 C39 175.2(8) . . . . ?
C28 C29 C30 C31 -177.6(8) . . . . ?
C28 C29 C30 C37 4.4(13) . . . . ?
C28 C29 C34 C33 176.3(8) . . . . ?
C28 C29 C34 C35 -4.3(12) . . . . ?
C28 C38 C39 C40 -178.4(9) . . . . ?
C28 C38 C39 C43 -2.8(15) . . . . ?
C29 C28 C38 N4 179.7(7) . . . . ?
C29 C28 C38 C39 -1.9(13) . . . . ?
C29 C30 C31 C32 1.7(13) . . . . ?
C30 C29 C34 C33 -1.9(13) . . . . ?
C30 C29 C34 C35 177.5(8) . . . . ?
C30 C31 C32 C33 -2.6(14) . . . . ?
C30 C31 C32 C36 178.0(9) . . . . ?
C31 C32 C33 C34 1.2(14) . . . . ?
C32 C33 C34 C29 0.9(14) . . . . ?
C32 C33 C34 C35 -178.5(9) . . . . ?
C34 C29 C30 C31 0.6(13) . . . . ?
C34 C29 C30 C37 -177.4(8) . . . . ?
C36 C32 C33 C34 -179.4(9) . . . . ?
C37 C30 C31 C32 179.7(9) . . . . ?
C38 N4 C41 C40 0.2(9) . . . . ?
C38 N4 C41 C42 -177.9(7) . . . . ?
C38 C28 C29 C30 84.4(10) . . . . ?
C38 C28 C29 C34 -93.8(10) . . . . ?
C38 C39 C40 C41 -0.2(10) . . . . ?
C39 C40 C41 N4 0.0(10) . . . . ?
C39 C40 C41 C42 178.0(8) . . . . ?
C41 N4 C38 C28 178.5(8) . . . . ?
C41 N4 C38 C39 -0.3(9) . . . . ?
C43 C39 C40 C41 -176.1(8) . . . . ?
C44 C26 C27 N3 178.2(9) . . . . ?
C44 C26 C27 C28 -9.6(16) . . . . ?
