# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1948644'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2020-04-03 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H27 Bi'
_chemical_formula_sum            'C36 H27 Bi'
_chemical_formula_weight         668.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0767(1)
_cell_length_b                   20.4313(1)
_cell_length_c                   13.8429(1)
_cell_angle_alpha                90
_cell_angle_beta                 109.817(1)
_cell_angle_gamma                90
_cell_volume                     2681.20(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120
_cell_measurement_reflns_used    13843
_cell_measurement_theta_min      4.0090
_cell_measurement_theta_max      67.5840

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    13.062
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.62060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.756
_oxdiff_exptl_absorpt_empirical_full_max 1.442
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23124
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.025
_diffrn_reflns_theta_max         67.744
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4819
_reflns_number_gt                4394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+1.9761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4819
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.0040(3) 0.01065(17) 0.7163(3) 0.0133(7) Uani 1 1 d . . . . .
C2 C -0.1209(4) 0.01898(18) 0.7383(3) 0.0177(7) Uani 1 1 d . . . . .
H2 H -0.1360 0.0576 0.7685 0.021 Uiso 1 1 calc R U . . .
C3 C -0.2230(4) -0.0306(2) 0.7151(3) 0.0207(8) Uani 1 1 d . . . . .
H3 H -0.3065 -0.0246 0.7286 0.025 Uiso 1 1 calc R U . . .
C4 C -0.1989(4) -0.08856(19) 0.6721(3) 0.0221(8) Uani 1 1 d . . . . .
H4 H -0.2663 -0.1216 0.6572 0.027 Uiso 1 1 calc R U . . .
C5 C -0.0752(4) -0.09789(18) 0.6511(3) 0.0208(8) Uani 1 1 d . . . . .
H5 H -0.0599 -0.1371 0.6222 0.025 Uiso 1 1 calc R U . . .
C6 C 0.0275(4) -0.04805(18) 0.6733(3) 0.0156(7) Uani 1 1 d . . . . .
C7 C 0.1600(4) -0.06057(17) 0.6504(3) 0.0162(7) Uani 1 1 d . . . . .
C8 C 0.2489(4) -0.11169(19) 0.6989(3) 0.0230(8) Uani 1 1 d . . . . .
H8 H 0.2276 -0.1370 0.7476 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3699(4) -0.1251(2) 0.6748(3) 0.0312(10) Uani 1 1 d . . . . .
H9 H 0.4289 -0.1593 0.7072 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4020(4) -0.0873(2) 0.6025(4) 0.0320(10) Uani 1 1 d . . . . .
H10 H 0.4821 -0.0966 0.5860 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3164(4) -0.0365(2) 0.5555(3) 0.0272(9) Uani 1 1 d . . . . .
H11 H 0.3389 -0.0111 0.5075 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1949(4) -0.02241(19) 0.5790(3) 0.0201(8) Uani 1 1 d . . . . .
H12 H 0.1375 0.0124 0.5470 0.024 Uiso 1 1 calc R U . . .
C21 C 0.0970(3) 0.13797(17) 0.8770(3) 0.0140(7) Uani 1 1 d . . . . .
C22 C 0.0173(4) 0.19524(18) 0.8493(3) 0.0173(7) Uani 1 1 d . . . . .
H22 H -0.0084 0.2105 0.7822 0.021 Uiso 1 1 calc R U . . .
C23 C -0.0242(4) 0.22962(18) 0.9210(3) 0.0204(8) Uani 1 1 d . . . . .
H23 H -0.0789 0.2672 0.9014 0.025 Uiso 1 1 calc R U . . .
C24 C 0.0157(4) 0.2081(2) 1.0213(3) 0.0237(8) Uani 1 1 d . . . . .
H24 H -0.0120 0.2311 1.0693 0.028 Uiso 1 1 calc R U . . .
C25 C 0.0967(4) 0.1524(2) 1.0503(3) 0.0237(8) Uani 1 1 d . . . . .
H25 H 0.1242 0.1383 1.1181 0.028 Uiso 1 1 calc R U . . .
C26 C 0.1382(4) 0.11674(17) 0.9788(3) 0.0161(7) Uani 1 1 d . . . . .
C27 C 0.2284(4) 0.05736(18) 1.0149(3) 0.0168(7) Uani 1 1 d . . . . .
C28 C 0.3669(4) 0.06393(19) 1.0807(3) 0.0220(8) Uani 1 1 d . . . . .
H28 H 0.4036 0.1054 1.1016 0.026 Uiso 1 1 calc R U . . .
C29 C 0.4504(4) 0.0093(2) 1.1154(3) 0.0254(9) Uani 1 1 d . . . . .
H29 H 0.5430 0.0143 1.1591 0.031 Uiso 1 1 calc R U . . .
C30 C 0.3976(4) -0.0525(2) 1.0857(3) 0.0270(9) Uani 1 1 d . . . . .
H30 H 0.4542 -0.0892 1.1090 0.032 Uiso 1 1 calc R U . . .
C31 C 0.2592(5) -0.0595(2) 1.0209(3) 0.0287(9) Uani 1 1 d . . . . .
H31 H 0.2226 -0.1012 1.0014 0.034 Uiso 1 1 calc R U . . .
C32 C 0.1755(4) -0.00541(19) 0.9850(3) 0.0230(8) Uani 1 1 d . . . . .
H32 H 0.0833 -0.0107 0.9406 0.028 Uiso 1 1 calc R U . . .
C41 C 0.0870(4) 0.15639(17) 0.6405(3) 0.0154(7) Uani 1 1 d . . . . .
C42 C -0.0582(4) 0.16559(19) 0.5943(3) 0.0194(8) Uani 1 1 d . . . . .
H42 H -0.1199 0.1354 0.6064 0.023 Uiso 1 1 calc R U . . .
C43 C -0.1124(4) 0.2187(2) 0.5308(3) 0.0219(8) Uani 1 1 d . . . . .
H43 H -0.2094 0.2237 0.5003 0.026 Uiso 1 1 calc R U . . .
C44 C -0.0207(4) 0.26447(19) 0.5126(3) 0.0247(8) Uani 1 1 d . . . . .
H44 H -0.0562 0.3011 0.4722 0.030 Uiso 1 1 calc R U . . .
C45 C 0.1243(4) 0.2548(2) 0.5554(3) 0.0239(8) Uani 1 1 d . . . . .
H45 H 0.1854 0.2846 0.5416 0.029 Uiso 1 1 calc R U . . .
C46 C 0.1797(4) 0.20093(18) 0.6190(3) 0.0156(7) Uani 1 1 d . . . . .
C47 C 0.3348(4) 0.19018(17) 0.6607(3) 0.0146(7) Uani 1 1 d . . . . .
C48 C 0.3957(4) 0.14203(18) 0.6175(3) 0.0193(8) Uani 1 1 d . . . . .
H48 H 0.3387 0.1164 0.5638 0.023 Uiso 1 1 calc R U . . .
C49 C 0.5417(4) 0.13206(19) 0.6542(3) 0.0235(8) Uani 1 1 d . . . . .
H49 H 0.5811 0.0995 0.6255 0.028 Uiso 1 1 calc R U . . .
C50 C 0.6276(4) 0.1702(2) 0.7330(3) 0.0228(8) Uani 1 1 d . . . . .
H50 H 0.7248 0.1642 0.7565 0.027 Uiso 1 1 calc R U . . .
C51 C 0.5680(4) 0.21738(19) 0.7764(3) 0.0242(8) Uani 1 1 d . . . . .
H51 H 0.6255 0.2426 0.8302 0.029 Uiso 1 1 calc R U . . .
C52 C 0.4230(4) 0.22772(19) 0.7408(3) 0.0215(8) Uani 1 1 d . . . . .
H52 H 0.3846 0.2600 0.7708 0.026 Uiso 1 1 calc R U . . .
Bi1 Bi 0.18247(2) 0.08364(2) 0.76782(2) 0.01182(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.394(5) . ?
C1 C2 1.402(5) . ?
C1 Bi1 2.258(3) . ?
C2 C3 1.401(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(5) . ?
C7 C8 1.391(5) . ?
C7 C12 1.394(5) . ?
C8 C9 1.396(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C21 C26 1.396(5) . ?
C21 C22 1.397(5) . ?
C21 Bi1 2.267(3) . ?
C22 C23 1.391(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.402(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.496(5) . ?
C27 C28 1.391(5) . ?
C27 C32 1.397(5) . ?
C28 C29 1.382(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.378(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.386(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.377(6) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C41 C42 1.397(5) . ?
C41 C46 1.406(5) . ?
C41 Bi1 2.257(4) . ?
C42 C43 1.386(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.397(6) . ?
C43 H43 0.9300 . ?
C44 C45 1.393(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.402(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.487(5) . ?
C47 C52 1.393(5) . ?
C47 C48 1.397(5) . ?
C48 C49 1.399(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.381(6) . ?
C49 H49 0.9300 . ?
C50 C51 1.376(6) . ?
C50 H50 0.9300 . ?
C51 C52 1.391(5) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?

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
C6 C1 C2 119.5(3) . . ?
C6 C1 Bi1 118.1(2) . . ?
C2 C1 Bi1 121.9(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 C7 122.1(3) . . ?
C5 C6 C7 118.2(3) . . ?
C8 C7 C12 119.1(3) . . ?
C8 C7 C6 120.1(3) . . ?
C12 C7 C6 120.8(3) . . ?
C7 C8 C9 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.0(4) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C26 C21 C22 118.9(3) . . ?
C26 C21 Bi1 118.0(3) . . ?
C22 C21 Bi1 122.7(3) . . ?
C23 C22 C21 120.7(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.9(4) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 119.5(3) . . ?
C21 C26 C27 121.9(3) . . ?
C25 C26 C27 118.6(3) . . ?
C28 C27 C32 118.7(3) . . ?
C28 C27 C26 120.1(3) . . ?
C32 C27 C26 121.2(3) . . ?
C29 C28 C27 120.5(4) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.6(4) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.3(4) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C32 C31 C30 120.6(4) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C27 120.3(4) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?
C42 C41 C46 119.0(3) . . ?
C42 C41 Bi1 123.3(3) . . ?
C46 C41 Bi1 117.0(2) . . ?
C43 C42 C41 121.4(3) . . ?
C43 C42 H42 119.3 . . ?
C41 C42 H42 119.3 . . ?
C42 C43 C44 119.8(4) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
C45 C44 C43 119.4(4) . . ?
C45 C44 H44 120.3 . . ?
C43 C44 H44 120.3 . . ?
C44 C45 C46 121.0(3) . . ?
C44 C45 H45 119.5 . . ?
C46 C45 H45 119.5 . . ?
C45 C46 C41 119.3(3) . . ?
C45 C46 C47 120.1(3) . . ?
C41 C46 C47 120.6(3) . . ?
C52 C47 C48 118.3(3) . . ?
C52 C47 C46 122.0(3) . . ?
C48 C47 C46 119.6(3) . . ?
C47 C48 C49 120.5(4) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
C50 C49 C48 120.4(4) . . ?
C50 C49 H49 119.8 . . ?
C48 C49 H49 119.8 . . ?
C51 C50 C49 119.4(4) . . ?
C51 C50 H50 120.3 . . ?
C49 C50 H50 120.3 . . ?
C50 C51 C52 120.9(4) . . ?
C50 C51 H51 119.6 . . ?
C52 C51 H51 119.6 . . ?
C51 C52 C47 120.6(4) . . ?
C51 C52 H52 119.7 . . ?
C47 C52 H52 119.7 . . ?
C41 Bi1 C1 96.04(12) . . ?
C41 Bi1 C21 92.33(12) . . ?
C1 Bi1 C21 95.28(12) . . ?

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
C6 C1 C2 C3 -1.6(5) . . . . ?
Bi1 C1 C2 C3 -173.0(3) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C2 C1 C6 C5 1.1(5) . . . . ?
Bi1 C1 C6 C5 172.8(3) . . . . ?
C2 C1 C6 C7 -178.5(3) . . . . ?
Bi1 C1 C6 C7 -6.8(4) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
C1 C6 C7 C8 118.4(4) . . . . ?
C5 C6 C7 C8 -61.1(5) . . . . ?
C1 C6 C7 C12 -63.0(5) . . . . ?
C5 C6 C7 C12 117.5(4) . . . . ?
C12 C7 C8 C9 -1.1(6) . . . . ?
C6 C7 C8 C9 177.5(3) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 0.7(6) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C8 C7 C12 C11 1.3(5) . . . . ?
C6 C7 C12 C11 -177.4(3) . . . . ?
C10 C11 C12 C7 -0.4(6) . . . . ?
C26 C21 C22 C23 -1.9(5) . . . . ?
Bi1 C21 C22 C23 -175.2(3) . . . . ?
C21 C22 C23 C24 1.3(5) . . . . ?
C22 C23 C24 C25 0.0(6) . . . . ?
C23 C24 C25 C26 -0.7(6) . . . . ?
C22 C21 C26 C25 1.2(5) . . . . ?
Bi1 C21 C26 C25 174.8(3) . . . . ?
C22 C21 C26 C27 -177.5(3) . . . . ?
Bi1 C21 C26 C27 -4.0(4) . . . . ?
C24 C25 C26 C21 0.0(6) . . . . ?
C24 C25 C26 C27 178.9(4) . . . . ?
C21 C26 C27 C28 110.4(4) . . . . ?
C25 C26 C27 C28 -68.4(5) . . . . ?
C21 C26 C27 C32 -70.7(5) . . . . ?
C25 C26 C27 C32 110.5(4) . . . . ?
C32 C27 C28 C29 0.3(5) . . . . ?
C26 C27 C28 C29 179.2(4) . . . . ?
C27 C28 C29 C30 -0.3(6) . . . . ?
C28 C29 C30 C31 -0.3(6) . . . . ?
C29 C30 C31 C32 0.9(6) . . . . ?
C30 C31 C32 C27 -1.0(6) . . . . ?
C28 C27 C32 C31 0.4(6) . . . . ?
C26 C27 C32 C31 -178.5(4) . . . . ?
C46 C41 C42 C43 -2.1(5) . . . . ?
Bi1 C41 C42 C43 167.5(3) . . . . ?
C41 C42 C43 C44 -0.5(6) . . . . ?
C42 C43 C44 C45 2.5(6) . . . . ?
C43 C44 C45 C46 -2.0(6) . . . . ?
C44 C45 C46 C41 -0.6(6) . . . . ?
C44 C45 C46 C47 177.6(4) . . . . ?
C42 C41 C46 C45 2.6(5) . . . . ?
Bi1 C41 C46 C45 -167.7(3) . . . . ?
C42 C41 C46 C47 -175.6(3) . . . . ?
Bi1 C41 C46 C47 14.1(4) . . . . ?
C45 C46 C47 C52 75.2(5) . . . . ?
C41 C46 C47 C52 -106.6(4) . . . . ?
C45 C46 C47 C48 -103.5(4) . . . . ?
C41 C46 C47 C48 74.7(5) . . . . ?
C52 C47 C48 C49 0.1(5) . . . . ?
C46 C47 C48 C49 178.7(3) . . . . ?
C47 C48 C49 C50 -0.8(6) . . . . ?
C48 C49 C50 C51 1.3(6) . . . . ?
C49 C50 C51 C52 -1.1(6) . . . . ?
C50 C51 C52 C47 0.4(6) . . . . ?
C48 C47 C52 C51 0.1(6) . . . . ?
C46 C47 C52 C51 -178.5(3) . . . . ?

_refine_diff_density_max         0.914
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.104

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1948647'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 Bi'
_chemical_formula_sum            'C25 H21 Bi'
_chemical_formula_weight         530.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   15.1772(5)
_cell_length_b                   6.7889(3)
_cell_length_c                   19.2090(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.773(3)
_cell_angle_gamma                90
_cell_volume                     1950.51(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    10804
_cell_measurement_theta_min      4.0090
_cell_measurement_theta_max      67.5560


_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -5 0.0085
-6 0 11 0.0163
-6 0 -8 0.0979
0 0 0 0.0292
0 0 0 0.0485
0 0 0 1.2236
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0101 0.0052 -5.0006 -0.3951 0.0147 -0.0966
-5.7432 -0.0972 11.2202 0.8022 0.5551 0.2199
-6.3802 0.1595 -7.9839 -0.7106 0.6731 -0.2050
0.2071 0.0023 -0.0016 0.0029 -0.0211 0.0000
0.1567 0.0039 -0.1973 -0.0132 -0.0154 -0.0042
0.1451 0.2508 -0.1754 0.0016 -0.0139 -0.0582
_exptl_absorpt_coefficient_mu    17.710
_exptl_absorpt_correction_T_min  0.023
_exptl_absorpt_correction_T_max  0.673
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.600
_oxdiff_exptl_absorpt_empirical_full_max 2.197
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku oxford gemini s'
_diffrn_measurement_method       'w\ scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28460
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         67.800
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.900
_reflns_number_total             6360
_reflns_number_gt                5599
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_max     0.814
_reflns_Friedel_fraction_full    0.816

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0993P)²+5.1701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.059(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6360
_refine_ls_number_parameters     469
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1422
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.9051(14) -0.412(3) 0.1887(10) 0.045(5) Uani 1 1 d . . . . .
H1A H 0.9065 -0.4988 0.1495 0.067 Uiso 1 1 calc R U . . .
H1B H 0.8524 -0.3314 0.1794 0.067 Uiso 1 1 calc R U . . .
H1C H 0.9043 -0.4881 0.2307 0.067 Uiso 1 1 calc R U . . .
C2 C 0.9672(11) 0.013(3) 0.1252(9) 0.034(4) Uani 1 1 d . . . . .
C3 C 0.8797(10) -0.007(3) 0.0887(8) 0.032(4) Uani 1 1 d . . . . .
H3 H 0.8437 -0.1069 0.1012 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8457(11) 0.120(3) 0.0342(10) 0.039(4) Uani 1 1 d . . . . .
H4 H 0.7871 0.1062 0.0111 0.047 Uiso 1 1 calc R U . . .
C5 C 0.8995(11) 0.268(5) 0.0142(8) 0.042(4) Uani 1 1 d . . . . .
H5 H 0.8771 0.3507 -0.0233 0.050 Uiso 1 1 calc R U . . .
C6 C 0.9848(11) 0.294(5) 0.0491(8) 0.037(4) Uani 1 1 d . . . . .
H6 H 1.0197 0.3947 0.0356 0.045 Uiso 1 1 calc R U . . .
C7 C 1.0204(11) 0.169(3) 0.1054(9) 0.033(4) Uani 1 1 d . . . . .
C8 C 1.1130(11) 0.202(3) 0.1427(10) 0.036(4) Uani 1 1 d . . . . .
C9 C 1.1302(9) 0.230(3) 0.2119(8) 0.035(6) Uani 1 1 d . . . . .
H9 H 1.0825 0.2432 0.2363 0.042 Uiso 1 1 calc R U . . .
C10 C 1.2191(13) 0.241(4) 0.2506(10) 0.046(7) Uani 1 1 d . . . . .
H10 H 1.2301 0.2381 0.2997 0.056 Uiso 1 1 calc R U . . .
C11 C 1.2876(13) 0.255(5) 0.2125(10) 0.056(7) Uani 1 1 d . . . . .
H11 H 1.3455 0.2791 0.2357 0.067 Uiso 1 1 calc R U . . .
C12 C 1.2713(13) 0.233(3) 0.1405(10) 0.042(6) Uani 1 1 d . . . . .
H12 H 1.3185 0.2309 0.1154 0.050 Uiso 1 1 calc R U . . .
C13 C 1.1836(12) 0.213(3) 0.1052(10) 0.043(5) Uani 1 1 d . . . . .
H13 H 1.1722 0.2080 0.0561 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9804(10) -0.072(2) 0.2963(7) 0.024(3) Uani 1 1 d . . . . .
C15 C 0.9136(10) 0.073(3) 0.2862(8) 0.026(3) Uani 1 1 d . . . . .
H15 H 0.8930 0.1182 0.2406 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8770(11) 0.153(3) 0.3417(9) 0.033(4) Uani 1 1 d . . . . .
H16 H 0.8344 0.2527 0.3332 0.039 Uiso 1 1 calc R U . . .
C17 C 0.9050(11) 0.082(3) 0.4107(9) 0.033(4) Uani 1 1 d . . . . .
H17 H 0.8792 0.1286 0.4481 0.040 Uiso 1 1 calc R U . . .
C18 C 0.9721(11) -0.060(3) 0.4217(9) 0.035(4) Uani 1 1 d . . . . .
H18 H 0.9934 -0.1034 0.4674 0.042 Uiso 1 1 calc R U . . .
C19 C 1.0086(11) -0.139(2) 0.3645(9) 0.032(4) Uani 1 1 d . . . . .
C20 C 1.0786(11) -0.296(3) 0.3826(9) 0.029(4) Uani 1 1 d . . . . .
C21 C 1.0564(11) -0.485(3) 0.3948(9) 0.034(4) Uani 1 1 d . . . . .
H21 H 0.9961 -0.5176 0.3895 0.040 Uiso 1 1 calc R U . . .
C22 C 1.1204(13) -0.632(3) 0.4152(9) 0.039(4) Uani 1 1 d . . . . .
H22 H 1.1034 -0.7611 0.4229 0.047 Uiso 1 1 calc R U . . .
C23 C 1.2110(12) -0.578(3) 0.4234(9) 0.040(4) Uani 1 1 d . . . . .
H23 H 1.2554 -0.6701 0.4391 0.048 Uiso 1 1 calc R U . . .
C24 C 1.2335(12) -0.391(3) 0.4082(10) 0.041(4) Uani 1 1 d . . . . .
H24 H 1.2935 -0.3580 0.4118 0.049 Uiso 1 1 calc R U . . .
C25 C 1.1695(11) -0.251(4) 0.3878(9) 0.038(5) Uani 1 1 d . . . . .
H25 H 1.1866 -0.1239 0.3773 0.045 Uiso 1 1 calc R U . . .
C31 C 0.6764(13) 0.091(3) 0.1920(10) 0.046(5) Uani 1 1 d . . . . .
H31A H 0.6580 0.0041 0.1529 0.069 Uiso 1 1 calc R U . . .
H31B H 0.6961 0.0152 0.2339 0.069 Uiso 1 1 calc R U . . .
H31C H 0.7247 0.1726 0.1823 0.069 Uiso 1 1 calc R U . . .
C32 C 0.5853(11) 0.517(3) 0.1283(9) 0.034(4) Uani 1 1 d . . . . .
C33 C 0.6562(11) 0.497(3) 0.0904(9) 0.038(4) Uani 1 1 d . . . . .
H33 H 0.6979 0.3972 0.1024 0.045 Uiso 1 1 calc R U . . .
C34 C 0.6655(14) 0.623(3) 0.0358(10) 0.046(5) Uani 1 1 d . . . . .
H34 H 0.7129 0.6086 0.0112 0.056 Uiso 1 1 calc R U . . .
C35 C 0.6039(11) 0.769(4) 0.0184(8) 0.039(4) Uani 1 1 d . . . . .
H35 H 0.6099 0.8540 -0.0185 0.046 Uiso 1 1 calc R U . . .
C36 C 0.5326(9) 0.795(5) 0.0543(8) 0.033(4) Uani 1 1 d . . . . .
H36 H 0.4912 0.8947 0.0413 0.040 Uiso 1 1 calc R U . . .
C37 C 0.5235(12) 0.667(3) 0.1108(9) 0.036(4) Uani 1 1 d . . . . .
C38 C 0.4480(12) 0.697(3) 0.1491(10) 0.035(4) Uani 1 1 d . . . . .
C39 C 0.3600(11) 0.714(3) 0.1129(10) 0.038(5) Uani 1 1 d . . . . .
H39 H 0.3488 0.7130 0.0638 0.046 Uiso 1 1 calc R U . . .
C40 C 0.2899(13) 0.733(3) 0.1496(9) 0.041(5) Uani 1 1 d . . . . .
H40 H 0.2317 0.7385 0.1249 0.049 Uiso 1 1 calc R U . . .
C41 C 0.3044(13) 0.742(4) 0.2208(10) 0.049(7) Uani 1 1 d . . . . .
H41 H 0.2563 0.7542 0.2447 0.058 Uiso 1 1 calc R U . . .
C42 C 0.3905(13) 0.735(3) 0.2583(10) 0.044(6) Uani 1 1 d . . . . .
H42 H 0.4012 0.7389 0.3074 0.053 Uiso 1 1 calc R U . . .
C43 C 0.4613(11) 0.722(3) 0.2203(8) 0.035(5) Uani 1 1 d . . . . .
H43 H 0.5196 0.7294 0.2447 0.042 Uiso 1 1 calc R U . . .
C44 C 0.6509(10) 0.426(2) 0.3003(8) 0.027(3) Uani 1 1 d . U . . .
C45 C 0.7115(10) 0.575(3) 0.2870(9) 0.031(3) Uani 1 1 d . U . . .
H45 H 0.7099 0.6220 0.2413 0.037 Uiso 1 1 calc R U . . .
C46 C 0.7719(11) 0.650(3) 0.3410(9) 0.034(3) Uani 1 1 d . U . . .
H46 H 0.8108 0.7475 0.3311 0.040 Uiso 1 1 calc R U . . .
C47 C 0.7775(11) 0.587(2) 0.4090(9) 0.032(3) Uani 1 1 d . U . . .
H47 H 0.8196 0.6396 0.4450 0.038 Uiso 1 1 calc R U . . .
C48 C 0.7172(11) 0.439(3) 0.4229(9) 0.035(4) Uani 1 1 d . U . . .
H48 H 0.7199 0.3922 0.4688 0.042 Uiso 1 1 calc R U . . .
C49 C 0.6544(11) 0.363(2) 0.3691(9) 0.029(3) Uani 1 1 d . U . . .
C50 C 0.5936(12) 0.201(3) 0.3892(10) 0.035(4) Uani 1 1 d . . . . .
C51 C 0.4999(12) 0.247(4) 0.3816(10) 0.048(7) Uani 1 1 d . . . . .
H51 H 0.4772 0.3665 0.3625 0.057 Uiso 1 1 calc R U . . .
C52 C 0.4454(12) 0.107(3) 0.4039(10) 0.042(5) Uani 1 1 d . . . . .
H52 H 0.3842 0.1305 0.3985 0.051 Uiso 1 1 calc R U . . .
C53 C 0.4796(14) -0.071(4) 0.4344(10) 0.051(6) Uani 1 1 d . . . . .
H53 H 0.4420 -0.1601 0.4515 0.062 Uiso 1 1 calc R U . . .
C54 C 0.5694(14) -0.112(3) 0.4390(11) 0.055(6) Uani 1 1 d . . . . .
H54 H 0.5922 -0.2332 0.4563 0.066 Uiso 1 1 calc R U . . .
C55 C 0.6250(12) 0.027(3) 0.4177(10) 0.038(4) Uani 1 1 d . . . . .
H55 H 0.6859 0.0009 0.4229 0.045 Uiso 1 1 calc R U . . .
Bi1 Bi 1.02742(3) -0.21801(13) 0.20402(2) 0.0287(2) Uani 1 1 d . . . . .
Bi2 Bi 0.56159(3) 0.28096(13) 0.20799(2) 0.0287(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 Bi1 2.25(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.40(2) . ?
C2 C7 1.42(3) . ?
C2 Bi1 2.263(18) . ?
C3 C4 1.39(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.39(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.36(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.41(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.48(2) . ?
C8 C9 1.33(2) . ?
C8 C13 1.39(2) . ?
C9 C10 1.43(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.37(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.37(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.39(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.38(2) . ?
C14 C15 1.41(2) . ?
C14 Bi1 2.249(14) . ?
C15 C16 1.39(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.41(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.39(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.42(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.50(2) . ?
C20 C21 1.36(3) . ?
C20 C25 1.40(2) . ?
C21 C22 1.41(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.41(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.36(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.37(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C31 Bi2 2.23(2) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C37 1.39(3) . ?
C32 C33 1.41(2) . ?
C32 Bi2 2.285(17) . ?
C33 C34 1.38(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.36(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.39(2) . ?
C35 H35 0.9300 . ?
C36 C37 1.41(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.48(3) . ?
C38 C43 1.36(2) . ?
C38 C39 1.40(2) . ?
C39 C40 1.38(3) . ?
C39 H39 0.9300 . ?
C40 C41 1.35(3) . ?
C40 H40 0.9300 . ?
C41 C42 1.38(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.40(2) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 C49 1.38(2) . ?
C44 C45 1.42(2) . ?
C44 Bi2 2.265(16) . ?
C45 C46 1.36(2) . ?
C45 H45 0.9300 . ?
C46 C47 1.36(2) . ?
C46 H46 0.9300 . ?
C47 C48 1.42(3) . ?
C47 H47 0.9300 . ?
C48 C49 1.38(2) . ?
C48 H48 0.9300 . ?
C49 C50 1.53(2) . ?
C50 C55 1.36(3) . ?
C50 C51 1.44(2) . ?
C51 C52 1.38(3) . ?
C51 H51 0.9300 . ?
C52 C53 1.40(3) . ?
C52 H52 0.9300 . ?
C53 C54 1.38(3) . ?
C53 H53 0.9300 . ?
C54 C55 1.37(3) . ?
C54 H54 0.9300 . ?
C55 H55 0.9300 . ?

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
Bi1 C1 H1A 109.5 . . ?
Bi1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Bi1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.1(16) . . ?
C3 C2 Bi1 120.6(14) . . ?
C7 C2 Bi1 120.8(12) . . ?
C4 C3 C2 121.2(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.9(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 119.5(17) . . ?
C6 C7 C8 119.2(17) . . ?
C2 C7 C8 121.3(16) . . ?
C9 C8 C13 118.2(16) . . ?
C9 C8 C7 121.1(15) . . ?
C13 C8 C7 120.6(16) . . ?
C8 C9 C10 122.5(15) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C11 C10 C9 117.5(17) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
C12 C11 C10 120.4(19) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.7(17) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 120.6(17) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C19 C14 C15 117.4(14) . . ?
C19 C14 Bi1 121.0(12) . . ?
C15 C14 Bi1 121.2(10) . . ?
C16 C15 C14 122.7(15) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C17 119.4(16) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 118.5(16) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C19 121.1(16) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 120.9(16) . . ?
C14 C19 C20 122.9(15) . . ?
C18 C19 C20 116.3(15) . . ?
C21 C20 C25 117.9(18) . . ?
C21 C20 C19 121.5(15) . . ?
C25 C20 C19 120.6(17) . . ?
C20 C21 C22 122.8(16) . . ?
C20 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
C23 C22 C21 117.5(18) . . ?
C23 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
C24 C23 C22 119.7(18) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 121.4(18) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C20 121(2) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
Bi2 C31 H31A 109.5 . . ?
Bi2 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
Bi2 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C37 C32 C33 119.3(16) . . ?
C37 C32 Bi2 120.1(13) . . ?
C33 C32 Bi2 120.2(13) . . ?
C34 C33 C32 121.5(18) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C35 C34 C33 118.9(18) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 C36 122(2) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C35 C36 C37 119(2) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C32 C37 C36 119.2(18) . . ?
C32 C37 C38 122.0(16) . . ?
C36 C37 C38 118.8(18) . . ?
C43 C38 C39 117.1(16) . . ?
C43 C38 C37 121.5(15) . . ?
C39 C38 C37 121.3(16) . . ?
C40 C39 C38 120.5(17) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C41 C40 C39 121.1(18) . . ?
C41 C40 H40 119.5 . . ?
C39 C40 H40 119.5 . . ?
C40 C41 C42 120.2(19) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C41 C42 C43 118.1(16) . . ?
C41 C42 H42 120.9 . . ?
C43 C42 H42 120.9 . . ?
C38 C43 C42 122.5(15) . . ?
C38 C43 H43 118.7 . . ?
C42 C43 H43 118.7 . . ?
C49 C44 C45 118.1(15) . . ?
C49 C44 Bi2 122.5(12) . . ?
C45 C44 Bi2 119.2(12) . . ?
C46 C45 C44 120.1(16) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C47 122.7(17) . . ?
C45 C46 H46 118.7 . . ?
C47 C46 H46 118.7 . . ?
C46 C47 C48 117.8(16) . . ?
C46 C47 H47 121.1 . . ?
C48 C47 H47 121.1 . . ?
C49 C48 C47 120.5(17) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C48 C49 C44 120.9(16) . . ?
C48 C49 C50 116.6(15) . . ?
C44 C49 C50 122.5(15) . . ?
C55 C50 C51 120(2) . . ?
C55 C50 C49 123.0(16) . . ?
C51 C50 C49 116.6(18) . . ?
C52 C51 C50 117(2) . . ?
C52 C51 H51 121.5 . . ?
C50 C51 H51 121.5 . . ?
C51 C52 C53 121.8(18) . . ?
C51 C52 H52 119.1 . . ?
C53 C52 H52 119.1 . . ?
C54 C53 C52 119.6(19) . . ?
C54 C53 H53 120.2 . . ?
C52 C53 H53 120.2 . . ?
C53 C54 C55 119(2) . . ?
C53 C54 H54 120.3 . . ?
C55 C54 H54 120.3 . . ?
C50 C55 C54 122.0(19) . . ?
C50 C55 H55 119.0 . . ?
C54 C55 H55 119.0 . . ?
C14 Bi1 C1 89.7(6) . . ?
C14 Bi1 C2 94.4(6) . . ?
C1 Bi1 C2 95.0(7) . . ?
C31 Bi2 C44 88.9(6) . . ?
C31 Bi2 C32 95.6(7) . . ?
C44 Bi2 C32 94.5(6) . . ?

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
C7 C2 C3 C4 1(3) . . . . ?
Bi1 C2 C3 C4 -171.9(13) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C3 C4 C5 C6 -2(3) . . . . ?
C4 C5 C6 C7 1(3) . . . . ?
C5 C6 C7 C2 1(3) . . . . ?
C5 C6 C7 C8 -179.3(19) . . . . ?
C3 C2 C7 C6 -2(3) . . . . ?
Bi1 C2 C7 C6 171.0(14) . . . . ?
C3 C2 C7 C8 178.5(16) . . . . ?
Bi1 C2 C7 C8 -9(2) . . . . ?
C6 C7 C8 C9 124(2) . . . . ?
C2 C7 C8 C9 -56(3) . . . . ?
C6 C7 C8 C13 -53(3) . . . . ?
C2 C7 C8 C13 126.6(19) . . . . ?
C13 C8 C9 C10 -10(3) . . . . ?
C7 C8 C9 C10 172.8(19) . . . . ?
C8 C9 C10 C11 11(4) . . . . ?
C9 C10 C11 C12 -8(4) . . . . ?
C10 C11 C12 C13 6(4) . . . . ?
C9 C8 C13 C12 7(3) . . . . ?
C7 C8 C13 C12 -176.1(18) . . . . ?
C11 C12 C13 C8 -5(3) . . . . ?
C19 C14 C15 C16 1(2) . . . . ?
Bi1 C14 C15 C16 173.8(12) . . . . ?
C14 C15 C16 C17 -2(2) . . . . ?
C15 C16 C17 C18 3(2) . . . . ?
C16 C17 C18 C19 -3(3) . . . . ?
C15 C14 C19 C18 -1(2) . . . . ?
Bi1 C14 C19 C18 -173.7(12) . . . . ?
C15 C14 C19 C20 179.1(15) . . . . ?
Bi1 C14 C19 C20 6(2) . . . . ?
C17 C18 C19 C14 2(3) . . . . ?
C17 C18 C19 C20 -178.0(16) . . . . ?
C14 C19 C20 C21 -101(2) . . . . ?
C18 C19 C20 C21 79(2) . . . . ?
C14 C19 C20 C25 79(2) . . . . ?
C18 C19 C20 C25 -100.9(19) . . . . ?
C25 C20 C21 C22 3(3) . . . . ?
C19 C20 C21 C22 -176.8(16) . . . . ?
C20 C21 C22 C23 0(3) . . . . ?
C21 C22 C23 C24 -3(3) . . . . ?
C22 C23 C24 C25 3(3) . . . . ?
C23 C24 C25 C20 1(3) . . . . ?
C21 C20 C25 C24 -3(3) . . . . ?
C19 C20 C25 C24 176.3(16) . . . . ?
C37 C32 C33 C34 0(3) . . . . ?
Bi2 C32 C33 C34 171.6(14) . . . . ?
C32 C33 C34 C35 0(3) . . . . ?
C33 C34 C35 C36 0(3) . . . . ?
C34 C35 C36 C37 0(3) . . . . ?
C33 C32 C37 C36 1(3) . . . . ?
Bi2 C32 C37 C36 -171.0(14) . . . . ?
C33 C32 C37 C38 -179.2(16) . . . . ?
Bi2 C32 C37 C38 9(2) . . . . ?
C35 C36 C37 C32 -1(3) . . . . ?
C35 C36 C37 C38 179.2(18) . . . . ?
C32 C37 C38 C43 55(3) . . . . ?
C36 C37 C38 C43 -125(2) . . . . ?
C32 C37 C38 C39 -128.7(19) . . . . ?
C36 C37 C38 C39 51(3) . . . . ?
C43 C38 C39 C40 -7(3) . . . . ?
C37 C38 C39 C40 176.7(17) . . . . ?
C38 C39 C40 C41 3(3) . . . . ?
C39 C40 C41 C42 0(4) . . . . ?
C40 C41 C42 C43 1(4) . . . . ?
C39 C38 C43 C42 9(3) . . . . ?
C37 C38 C43 C42 -174.9(18) . . . . ?
C41 C42 C43 C38 -6(3) . . . . ?
C49 C44 C45 C46 1(2) . . . . ?
Bi2 C44 C45 C46 -173.3(12) . . . . ?
C44 C45 C46 C47 0(3) . . . . ?
C45 C46 C47 C48 0(3) . . . . ?
C46 C47 C48 C49 -1(3) . . . . ?
C47 C48 C49 C44 2(3) . . . . ?
C47 C48 C49 C50 178.9(15) . . . . ?
C45 C44 C49 C48 -2(2) . . . . ?
Bi2 C44 C49 C48 172.1(12) . . . . ?
C45 C44 C49 C50 -178.9(15) . . . . ?
Bi2 C44 C49 C50 -5(2) . . . . ?
C48 C49 C50 C55 -60(2) . . . . ?
C44 C49 C50 C55 117(2) . . . . ?
C48 C49 C50 C51 115.1(19) . . . . ?
C44 C49 C50 C51 -68(2) . . . . ?
C55 C50 C51 C52 0(3) . . . . ?
C49 C50 C51 C52 -176.0(17) . . . . ?
C50 C51 C52 C53 2(3) . . . . ?
C51 C52 C53 C54 -4(3) . . . . ?
C52 C53 C54 C55 4(3) . . . . ?
C51 C50 C55 C54 1(3) . . . . ?
C49 C50 C55 C54 176.3(18) . . . . ?
C53 C54 C55 C50 -3(3) . . . . ?

_refine_diff_density_max         4.754
_refine_diff_density_min         -1.543
_refine_diff_density_rms         0.227

_shelxl_version_number           2013-4


# start Validation Reply Form
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.99A   From Bi2             4.71 eA-3  
RESPONSE: 

The ten highest unrefined electron density peaks (Q peaks) are located at:
0.95 A from Bi2 (Q1, 4.8 e A-3),
0.95 A from Bi1 (Q2, 4.6 e A-3),
0.98 A from Bi1 (Q3, 4.5 e A-3),
0.97 A from Bi2 (Q4, 3.9 e A-3),
2.19 A from C43 (Q5, 3.8 e A-3),
2.07 A from C9  (Q6, 2.5 e A-3),
1.33 A from C31 (Q7, 1.9 e A-3),
2.04 A from C41 (Q8, 1.9 e A-3),
0.36 A from C9  (Q9, 1.6 e A-3) and
0.48 A from C43 (Q10, 1.6 e A-3).

According to W. Massa (Kristallstrukturbestimmung, Teubner Studienbuecher, 
Stuttgart, 1996) and W. Clegg (Crystal Structure Determination, Oxford 
University Press, 1998) this might be observed for heavy atoms for which 
remaining density peaks with ca. 10% of the electron density of the heavy 
atom are expected at distances between 0.6 and 1.2 A - and accounts
for Q1-Q4.

The Q5 to Q8 peaks, respectively,are attributed to a non/resolvable twinning
of the crystals. The major domain comprises about 50 % of all reflection, while
the following three domains comprises about 20, 13 and 8 %. Separate integration
and combining reflections into one hklf5 file gave non-reliable results.
This is attributed to the very small rotation angle(s) of the domains with 
respect to each other. 


Based on:
_refine_diff_density_max    4.754
_refine_diff_density_min   -1.543


the q peaks starting from Q9 correspond then
to usually observed unrefined electron density peaks.



;
_vrf_PLAT973_shelx               
;
PROBLEM: Check Calcd Positive Resid. Density on       Bi2       3.19 eA-3  
RESPONSE: 

see above
;
_vrf_PLAT342_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02577 Ang.  
RESPONSE:

see above
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1948646'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Bi I'
_chemical_formula_sum            'C24 H19 Bi I'
_chemical_formula_weight         643.27

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.3194(9)
_cell_length_b                   9.6034(9)
_cell_length_c                   12.8339(12)
_cell_angle_alpha                108.743(3)
_cell_angle_beta                 99.713(3)
_cell_angle_gamma                103.712(3)
_cell_volume                     1018.57(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9873
_cell_measurement_theta_min      3.1087
_cell_measurement_theta_max      31.5399
_cell_measurement_temperature    100


_exptl_crystal_description       block
_exptl_crystal_colour            'clear light yellow'

_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.097
_exptl_crystal_F_000             598
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.312
_exptl_absorpt_coefficient_mu    10.174
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.04
_exptl_absorpt_correction_T_max  0.14


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'bruker venture d8'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15873
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.396
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3558
_reflns_number_gt                3356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'bruker instrument service APEX3v2017.3-0'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'

_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+8.8108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3558
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2615(12) 0.8394(12) 0.1803(9) 0.044(2) Uani 1 1 d . . . . .
C2 C 0.2621(13) 0.9081(13) 0.1007(9) 0.045(2) Uani 1 1 d . . . . .
H2 H 0.3562 0.9703 0.0979 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1294(15) 0.8873(15) 0.0265(10) 0.053(3) Uani 1 1 d . . . . .
H3 H 0.1314 0.9336 -0.0286 0.064 Uiso 1 1 calc R U . . .
C4 C -0.0110(14) 0.7979(14) 0.0306(10) 0.049(3) Uani 1 1 d . . . . .
H4 H -0.1038 0.7862 -0.0202 0.059 Uiso 1 1 calc R U . . .
C5 C -0.0138(13) 0.7287(13) 0.1069(9) 0.045(2) Uani 1 1 d . . . . .
H5 H -0.1085 0.6651 0.1075 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1223(12) 0.7498(12) 0.1856(9) 0.041(2) Uani 1 1 d . . . . .
C7 C 0.1162(12) 0.6719(13) 0.2693(10) 0.043(2) Uani 1 1 d . . . . .
C8 C 0.0467(13) 0.5144(14) 0.2322(11) 0.050(3) Uani 1 1 d . . . . .
H8 H -0.0065 0.4566 0.1542 0.059 Uiso 1 1 calc R U . . .
C9 C 0.0540(15) 0.4404(15) 0.3079(12) 0.057(3) Uani 1 1 d . . . . .
H9 H 0.0088 0.3314 0.2817 0.068 Uiso 1 1 calc R U . . .
C10 C 0.1278(14) 0.5258(16) 0.4227(11) 0.055(3) Uani 1 1 d . . . . .
H10 H 0.1353 0.4737 0.4741 0.066 Uiso 1 1 calc R U . . .
C11 C 0.1852(11) 0.6712(16) 0.4603(9) 0.046(3) Uani 1 1 d . . . . .
H11 H 0.2317 0.7264 0.5397 0.055 Uiso 1 1 calc R U . . .
C12 C 0.1817(12) 0.7560(13) 0.3847(10) 0.046(2) Uani 1 1 d . . . . .
H12 H 0.2232 0.8656 0.4136 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4817(12) 0.6310(12) 0.2338(9) 0.044(2) Uani 1 1 d . . . . .
C14 C 0.3999(13) 0.5361(13) 0.1234(10) 0.047(2) Uani 1 1 d . . . . .
H14 H 0.3290 0.5686 0.0821 0.057 Uiso 1 1 calc R U . . .
C15 C 0.4198(13) 0.3933(13) 0.0716(10) 0.048(2) Uani 1 1 d . . . . .
H15 H 0.3637 0.3285 -0.0048 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5249(13) 0.3460(15) 0.1346(11) 0.052(3) Uani 1 1 d . . . . .
H16 H 0.5394 0.2485 0.1009 0.062 Uiso 1 1 calc R U . . .
C17 C 0.6055(14) 0.4409(13) 0.2440(11) 0.054(3) Uani 1 1 d . . . . .
H17 H 0.6772 0.4089 0.2851 0.064 Uiso 1 1 calc R U . . .
C18 C 0.5852(12) 0.5838(13) 0.2969(10) 0.045(2) Uani 1 1 d . . . . .
C19 C 0.6709(12) 0.6834(12) 0.4170(10) 0.045(2) Uani 1 1 d . . . . .
C20 C 0.5991(13) 0.6924(13) 0.5048(10) 0.049(3) Uani 1 1 d . . . . .
H20 H 0.4936 0.6365 0.4872 0.059 Uiso 1 1 calc R U . . .
C21 C 0.6800(14) 0.7824(13) 0.6180(10) 0.050(3) Uani 1 1 d . . . . .
H21 H 0.6302 0.7865 0.6772 0.061 Uiso 1 1 calc R U . . .
C22 C 0.8354(14) 0.8669(14) 0.6445(10) 0.051(3) Uani 1 1 d . . . . .
H22 H 0.8914 0.9299 0.7212 0.061 Uiso 1 1 calc R U . . .
C23 C 0.9043(14) 0.8568(14) 0.5577(10) 0.051(3) Uani 1 1 d . . . . .
H23 H 1.0099 0.9124 0.5751 0.061 Uiso 1 1 calc R U . . .
C24 C 0.8244(13) 0.7675(13) 0.4448(10) 0.048(2) Uani 1 1 d . . . . .
H24 H 0.8752 0.7639 0.3862 0.058 Uiso 1 1 calc R U . . .
Bi1 Bi 0.47302(4) 0.87330(4) 0.31380(3) 0.04214(18) Uani 1 1 d . . . . .
HI1 H 0.5359 0.9595 0.3802 0.051 Uiso 1 1 calc R U . . .
I1 I 0.68578(8) 0.99986(8) 0.20371(6) 0.0480(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.383(16) . ?
C1 C6 1.402(15) . ?
C1 Bi1 2.264(11) . ?
C2 C3 1.356(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.349(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.494(15) . ?
C7 C8 1.380(16) . ?
C7 C12 1.382(16) . ?
C8 C9 1.377(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.263(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.455(16) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.377(16) . ?
C13 C18 1.403(15) . ?
C13 Bi1 2.248(11) . ?
C14 C15 1.391(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.413(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.365(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.485(16) . ?
C19 C24 1.386(16) . ?
C19 C20 1.395(16) . ?
C20 C21 1.393(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.404(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.365(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(17) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
Bi1 I1 2.8829(8) . ?
Bi1 HI1 0.9500 . ?

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
C2 C1 C6 119.7(10) . . ?
C2 C1 Bi1 124.0(8) . . ?
C6 C1 Bi1 116.2(8) . . ?
C3 C2 C1 120.4(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.6(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.8(11) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.7(11) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.7(10) . . ?
C1 C6 C7 121.6(10) . . ?
C5 C6 C7 119.7(10) . . ?
C8 C7 C12 119.0(10) . . ?
C8 C7 C6 120.4(10) . . ?
C12 C7 C6 120.6(10) . . ?
C9 C8 C7 120.3(12) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.7(12) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 121.4(11) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 121.5(11) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 117.8(10) . . ?
C7 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C14 C13 C18 120.3(10) . . ?
C14 C13 Bi1 122.0(8) . . ?
C18 C13 Bi1 117.4(8) . . ?
C13 C14 C15 120.9(11) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 118.8(11) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 119.8(11) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.6(11) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 118.4(11) . . ?
C17 C18 C19 120.8(10) . . ?
C13 C18 C19 120.8(10) . . ?
C24 C19 C20 118.4(11) . . ?
C24 C19 C18 121.0(10) . . ?
C20 C19 C18 120.6(10) . . ?
C21 C20 C19 120.8(11) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.9(11) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 118.7(11) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C22 C23 C24 121.7(12) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C19 C24 C23 120.4(11) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C13 Bi1 C1 94.9(4) . . ?
C13 Bi1 I1 93.9(3) . . ?
C1 Bi1 I1 94.7(3) . . ?
C13 Bi1 HI1 132.6 . . ?
C1 Bi1 HI1 132.6 . . ?
I1 Bi1 HI1 83.6 . . ?

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
C6 C1 C2 C3 -1.1(16) . . . . ?
Bi1 C1 C2 C3 -177.2(8) . . . . ?
C1 C2 C3 C4 1.1(18) . . . . ?
C2 C3 C4 C5 -1.7(18) . . . . ?
C3 C4 C5 C6 2.4(17) . . . . ?
C2 C1 C6 C5 1.7(15) . . . . ?
Bi1 C1 C6 C5 178.1(8) . . . . ?
C2 C1 C6 C7 179.3(10) . . . . ?
Bi1 C1 C6 C7 -4.3(13) . . . . ?
C4 C5 C6 C1 -2.4(16) . . . . ?
C4 C5 C6 C7 180.0(10) . . . . ?
C1 C6 C7 C8 -124.5(12) . . . . ?
C5 C6 C7 C8 53.1(14) . . . . ?
C1 C6 C7 C12 54.6(14) . . . . ?
C5 C6 C7 C12 -127.8(11) . . . . ?
C12 C7 C8 C9 -5.5(16) . . . . ?
C6 C7 C8 C9 173.7(10) . . . . ?
C7 C8 C9 C10 2.0(17) . . . . ?
C8 C9 C10 C11 1.9(18) . . . . ?
C9 C10 C11 C12 -2.2(17) . . . . ?
C8 C7 C12 C11 5.1(14) . . . . ?
C6 C7 C12 C11 -174.0(9) . . . . ?
C10 C11 C12 C7 -1.3(15) . . . . ?
C18 C13 C14 C15 -1.0(17) . . . . ?
Bi1 C13 C14 C15 172.9(8) . . . . ?
C13 C14 C15 C16 0.5(17) . . . . ?
C14 C15 C16 C17 -0.5(18) . . . . ?
C15 C16 C17 C18 1.1(19) . . . . ?
C16 C17 C18 C13 -1.6(18) . . . . ?
C16 C17 C18 C19 178.3(11) . . . . ?
C14 C13 C18 C17 1.5(16) . . . . ?
Bi1 C13 C18 C17 -172.7(9) . . . . ?
C14 C13 C18 C19 -178.4(10) . . . . ?
Bi1 C13 C18 C19 7.4(13) . . . . ?
C17 C18 C19 C24 76.0(15) . . . . ?
C13 C18 C19 C24 -104.1(12) . . . . ?
C17 C18 C19 C20 -102.9(13) . . . . ?
C13 C18 C19 C20 77.0(14) . . . . ?
C24 C19 C20 C21 -0.7(16) . . . . ?
C18 C19 C20 C21 178.2(10) . . . . ?
C19 C20 C21 C22 0.8(17) . . . . ?
C20 C21 C22 C23 -1.0(16) . . . . ?
C21 C22 C23 C24 1.0(17) . . . . ?
C20 C19 C24 C23 0.7(16) . . . . ?
C18 C19 C24 C23 -178.2(10) . . . . ?
C22 C23 C24 C19 -0.9(17) . . . . ?

_refine_diff_density_max         4.718
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.260

_shelxl_version_number           2013-4



# start Validation Reply Form
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  1.55A   From Bi1             4.70 eA-3  
RESPONSE: 

The highest unrefined electron density peaks (Q peaks) are located at:
1.45 A from Bi1 (Q1, 4.7 e A-3),
0.90 A from Bi1 (Q2, 3.1 e A-3),
0.96 A from Bi1 (Q3, 2.9 e A-3),
0.93 A from Bi1 (Q4, 2.1 e A-3),
0.91 A from Bi1 (Q5, 2.0 e A-3,
0.96 A from I1 (Q6, 2.0 e A-3),

0.99 A from I1 (Q7, 2.0 e A-3),
0.89 A from I1 (Q8, 1.5 e A-3),
0.43 A from C11 (Q9, 1.5 e A-3),
0.85 A from I1 (Q10, 1.5 e A-3) and
0.71 A from C16 (Q11, 1.0 e A-3.


According to W. Massa (Kristallstrukturbestimmung, Teubner Studienbuecher, 
Stuttgart, 1996) and W. Clegg (Crystal Structure Determination, Oxford 
University Press, 1998) for heavy atoms  
remaining density peaks with ca. 10% of the electron density of the heavy 
atom are expected at distances between 0.6 and 1.2 A.

That accounts for Q2 to Q8 - and very likely for Q1 as well, although the 
distance is large. Noticeable, after isotropic refinement the Q1 peak
emerged in close proximity to Q1 (less than 1 A), while it shift
the position to larger distances after anisotropic refinement.

Furthermore, there is a comparatively large Q peak close to C11.
It is supposed that due to the fact that the atoms I1, Bi1 and C11 as
well as the q peaks Q1 and Q9 do all form a nearly straight line,
the absorption of reflexes along this line (crystal orientation)
is close to total absorption which is supposed as responsible for
this effect.
 
Based on:
_refine_diff_density_max    4.718
_refine_diff_density_min   -1.012
_refine_diff_density_rms    0.260 

the Q peaks starting
from Q11 are regarded as being due to the usually excpected  unrefined electron 
density peaks, cf.:


;
_vrf_PLAT094_shelx               
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.66 Report
RESPONSE: 

see above
;
# end Validation Reply Form


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1948649'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2020-04-03 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Bi2 I4'
_chemical_formula_sum            'C24 H18 Bi2 I4'
_chemical_formula_weight         1231.94

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.4889(9)
_cell_length_b                   9.9731(9)
_cell_length_c                   14.6288(13)
_cell_angle_alpha                102.420(3)
_cell_angle_beta                 93.506(3)
_cell_angle_gamma                92.701(3)
_cell_volume                     1346.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      3.0975
_cell_measurement_theta_max      25.6584

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.038
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    17.642
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.23976
_exptl_absorpt_correction_T_max  0.99999
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33289
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.671
_diffrn_reflns_theta_max         25.727
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5105
_reflns_number_gt                4945
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2017.3-0'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+9.3482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00178(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5105
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0609
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.4075(6) 0.0603(6) 0.2608(4) 0.0098(11) Uani 1 1 d . . . . .
C2 C 0.4890(6) -0.0249(6) 0.2010(4) 0.0131(12) Uani 1 1 d . . . . .
H10 H 0.5014 -0.0094 0.1401 0.016 Uiso 1 1 calc R U . . .
C3 C 0.5531(7) -0.1332(6) 0.2297(4) 0.0168(13) Uani 1 1 d . . . . .
H25 H 0.6121 -0.1894 0.1895 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5300(7) -0.1584(6) 0.3169(5) 0.0188(13) Uani 1 1 d . . . . .
H26 H 0.5713 -0.2338 0.3361 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4461(6) -0.0732(6) 0.3771(4) 0.0134(12) Uani 1 1 d . . . . .
H27 H 0.4289 -0.0924 0.4364 0.016 Uiso 1 1 calc R U . . .
C6 C 0.3878(6) 0.0391(6) 0.3509(4) 0.0115(11) Uani 1 1 d . . . . .
C7 C 0.3144(6) 0.1372(6) 0.4200(4) 0.0135(12) Uani 1 1 d . . . . .
C8 C 0.2037(7) 0.0904(7) 0.4661(4) 0.0186(13) Uani 1 1 d . . . . .
H31 H 0.1696 -0.0034 0.4493 0.022 Uiso 1 1 calc R U . . .
C9 C 0.1436(7) 0.1820(8) 0.5368(5) 0.0256(16) Uani 1 1 d . . . . .
H32 H 0.0703 0.1496 0.5695 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1892(7) 0.3182(8) 0.5596(5) 0.0259(16) Uani 1 1 d . . . . .
H1A H 0.1469 0.3800 0.6074 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2975(7) 0.3658(7) 0.5128(4) 0.0213(14) Uani 1 1 d . . . . .
H30 H 0.3291 0.4603 0.5283 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3598(7) 0.2745(6) 0.4429(4) 0.0149(12) Uani 1 1 d . . . . .
H29 H 0.4340 0.3071 0.4110 0.018 Uiso 1 1 calc R U . . .
C21 C -0.0483(6) 0.3838(6) 0.2499(4) 0.0125(12) Uani 1 1 d . . . . .
C22 C 0.0409(6) 0.4170(6) 0.3314(4) 0.0134(12) Uani 1 1 d . . . . .
H2 H 0.0344 0.3635 0.3776 0.016 Uiso 1 1 calc R U . . .
C23 C 0.1403(7) 0.5290(7) 0.3456(5) 0.0182(13) Uani 1 1 d . . . . .
H3 H 0.2014 0.5516 0.4014 0.022 Uiso 1 1 calc R U . . .
C24 C 0.1491(7) 0.6057(6) 0.2790(5) 0.0198(14) Uani 1 1 d . . . . .
H4 H 0.2173 0.6811 0.2884 0.024 Uiso 1 1 calc R U . . .
C25 C 0.0599(7) 0.5747(7) 0.1982(5) 0.0206(14) Uani 1 1 d . . . . .
H5 H 0.0650 0.6308 0.1534 0.025 Uiso 1 1 calc R U . . .
C26 C -0.0373(6) 0.4620(6) 0.1819(4) 0.0127(12) Uani 1 1 d . . . . .
C27 C -0.1331(6) 0.4286(6) 0.0941(4) 0.0132(12) Uani 1 1 d . . . . .
C28 C -0.1494(6) 0.2963(6) 0.0388(4) 0.0141(12) Uani 1 1 d . . . . .
H20 H -0.0911 0.2272 0.0523 0.017 Uiso 1 1 calc R U . . .
C29 C -0.2516(7) 0.2644(7) -0.0370(4) 0.0173(13) Uani 1 1 d . . . . .
H21 H -0.2662 0.1727 -0.0727 0.021 Uiso 1 1 calc R U . . .
C30 C -0.3309(7) 0.3660(7) -0.0597(4) 0.0176(13) Uani 1 1 d . . . . .
H22 H -0.4001 0.3442 -0.1113 0.021 Uiso 1 1 calc R U . . .
C31 C -0.3105(7) 0.5000(7) -0.0078(5) 0.0171(13) Uani 1 1 d . . . . .
H23 H -0.3643 0.5703 -0.0243 0.021 Uiso 1 1 calc R U . . .
C32 C -0.2116(7) 0.5309(6) 0.0683(4) 0.0157(12) Uani 1 1 d . . . . .
H24 H -0.1970 0.6230 0.1033 0.019 Uiso 1 1 calc R U . . .
I1 I 0.54028(4) 0.41910(4) 0.23080(3) 0.01315(10) Uani 1 1 d . . . . .
I2 I 0.29530(5) 0.11915(4) 0.01906(3) 0.01789(10) Uani 1 1 d . . . . .
I3 I 0.01653(4) 0.00707(4) 0.20863(3) 0.01471(10) Uani 1 1 d . . . . .
I4 I -0.23495(4) 0.21048(4) 0.41543(3) 0.01593(10) Uani 1 1 d . . . . .
Bi1 Bi 0.28223(2) 0.22268(2) 0.21447(2) 0.00973(7) Uani 1 1 d . . . . .
Bi2 Bi -0.21421(2) 0.20738(2) 0.22364(2) 0.01013(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.382(8) . ?
C1 C6 1.401(8) . ?
C1 Bi1 2.247(5) . ?
C2 C3 1.392(8) . ?
C2 H10 0.9500 . ?
C3 C4 1.381(9) . ?
C3 H25 0.9500 . ?
C4 C5 1.400(9) . ?
C4 H26 0.9500 . ?
C5 C6 1.387(8) . ?
C5 H27 0.9500 . ?
C6 C7 1.480(8) . ?
C7 C12 1.379(9) . ?
C7 C8 1.397(9) . ?
C8 C9 1.394(9) . ?
C8 H31 0.9500 . ?
C9 C10 1.370(11) . ?
C9 H32 0.9500 . ?
C10 C11 1.389(10) . ?
C10 H1A 0.9500 . ?
C11 C12 1.396(9) . ?
C11 H30 0.9500 . ?
C12 H29 0.9500 . ?
C21 C22 1.388(9) . ?
C21 C26 1.395(9) . ?
C21 Bi2 2.257(6) . ?
C22 C23 1.399(9) . ?
C22 H2 0.9500 . ?
C23 C24 1.365(10) . ?
C23 H3 0.9500 . ?
C24 C25 1.381(9) . ?
C24 H4 0.9500 . ?
C25 C26 1.390(9) . ?
C25 H5 0.9500 . ?
C26 C27 1.494(8) . ?
C27 C28 1.388(9) . ?
C27 C32 1.394(9) . ?
C28 C29 1.399(9) . ?
C28 H20 0.9500 . ?
C29 C30 1.374(9) . ?
C29 H21 0.9500 . ?
C30 C31 1.387(9) . ?
C30 H22 0.9500 . ?
C31 C32 1.382(9) . ?
C31 H23 0.9500 . ?
C32 H24 0.9500 . ?
I1 Bi1 3.0274(5) . ?
I1 Bi2 3.2086(5) 1_655 ?
I2 Bi1 2.8353(5) . ?
I3 Bi2 3.0191(5) . ?
I3 Bi1 3.2205(5) . ?
I4 Bi2 2.8183(5) . ?
Bi2 I1 3.2086(5) 1_455 ?

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
C2 C1 C6 120.7(5) . . ?
C2 C1 Bi1 122.3(4) . . ?
C6 C1 Bi1 116.7(4) . . ?
C1 C2 C3 120.3(6) . . ?
C1 C2 H10 119.8 . . ?
C3 C2 H10 119.8 . . ?
C4 C3 C2 119.5(6) . . ?
C4 C3 H25 120.2 . . ?
C2 C3 H25 120.2 . . ?
C3 C4 C5 120.2(6) . . ?
C3 C4 H26 119.9 . . ?
C5 C4 H26 119.9 . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 H27 119.7 . . ?
C4 C5 H27 119.7 . . ?
C5 C6 C1 118.5(5) . . ?
C5 C6 C7 119.5(5) . . ?
C1 C6 C7 121.8(5) . . ?
C12 C7 C8 119.6(6) . . ?
C12 C7 C6 120.1(6) . . ?
C8 C7 C6 120.3(6) . . ?
C9 C8 C7 119.7(6) . . ?
C9 C8 H31 120.2 . . ?
C7 C8 H31 120.2 . . ?
C10 C9 C8 120.6(7) . . ?
C10 C9 H32 119.7 . . ?
C8 C9 H32 119.7 . . ?
C9 C10 C11 119.9(6) . . ?
C9 C10 H1A 120.0 . . ?
C11 C10 H1A 120.0 . . ?
C10 C11 C12 119.9(7) . . ?
C10 C11 H30 120.1 . . ?
C12 C11 H30 120.1 . . ?
C7 C12 C11 120.3(6) . . ?
C7 C12 H29 119.8 . . ?
C11 C12 H29 119.8 . . ?
C22 C21 C26 119.6(6) . . ?
C22 C21 Bi2 122.1(4) . . ?
C26 C21 Bi2 118.3(4) . . ?
C21 C22 C23 120.2(6) . . ?
C21 C22 H2 119.9 . . ?
C23 C22 H2 119.9 . . ?
C24 C23 C22 119.7(6) . . ?
C24 C23 H3 120.2 . . ?
C22 C23 H3 120.2 . . ?
C23 C24 C25 120.7(6) . . ?
C23 C24 H4 119.6 . . ?
C25 C24 H4 119.6 . . ?
C24 C25 C26 120.4(6) . . ?
C24 C25 H5 119.8 . . ?
C26 C25 H5 119.8 . . ?
C25 C26 C21 119.4(6) . . ?
C25 C26 C27 120.2(6) . . ?
C21 C26 C27 120.4(5) . . ?
C28 C27 C32 118.9(6) . . ?
C28 C27 C26 121.4(5) . . ?
C32 C27 C26 119.6(5) . . ?
C27 C28 C29 120.2(6) . . ?
C27 C28 H20 119.9 . . ?
C29 C28 H20 119.9 . . ?
C30 C29 C28 119.9(6) . . ?
C30 C29 H21 120.0 . . ?
C28 C29 H21 120.0 . . ?
C29 C30 C31 120.3(6) . . ?
C29 C30 H22 119.8 . . ?
C31 C30 H22 119.8 . . ?
C32 C31 C30 119.7(6) . . ?
C32 C31 H23 120.1 . . ?
C30 C31 H23 120.1 . . ?
C31 C32 C27 120.8(6) . . ?
C31 C32 H24 119.6 . . ?
C27 C32 H24 119.6 . . ?
Bi1 I1 Bi2 100.114(14) . 1_655 ?
Bi2 I3 Bi1 98.170(14) . . ?
C1 Bi1 I2 96.25(15) . . ?
C1 Bi1 I1 92.88(14) . . ?
I2 Bi1 I1 94.078(13) . . ?
C1 Bi1 I3 84.07(14) . . ?
I2 Bi1 I3 88.367(13) . . ?
I1 Bi1 I3 176.289(12) . . ?
C21 Bi2 I4 94.45(16) . . ?
C21 Bi2 I3 89.74(14) . . ?
I4 Bi2 I3 92.031(13) . . ?
C21 Bi2 I1 90.34(14) . 1_455 ?
I4 Bi2 I1 90.211(12) . 1_455 ?
I3 Bi2 I1 177.743(12) . 1_455 ?

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
C6 C1 C2 C3 -0.1(9) . . . . ?
Bi1 C1 C2 C3 -173.3(4) . . . . ?
C1 C2 C3 C4 2.6(9) . . . . ?
C2 C3 C4 C5 -1.8(9) . . . . ?
C3 C4 C5 C6 -1.5(9) . . . . ?
C4 C5 C6 C1 3.9(9) . . . . ?
C4 C5 C6 C7 -172.5(6) . . . . ?
C2 C1 C6 C5 -3.1(9) . . . . ?
Bi1 C1 C6 C5 170.5(4) . . . . ?
C2 C1 C6 C7 173.2(6) . . . . ?
Bi1 C1 C6 C7 -13.2(7) . . . . ?
C5 C6 C7 C12 121.8(6) . . . . ?
C1 C6 C7 C12 -54.5(8) . . . . ?
C5 C6 C7 C8 -54.7(8) . . . . ?
C1 C6 C7 C8 129.0(6) . . . . ?
C12 C7 C8 C9 -2.1(9) . . . . ?
C6 C7 C8 C9 174.5(6) . . . . ?
C7 C8 C9 C10 1.9(10) . . . . ?
C8 C9 C10 C11 -0.7(10) . . . . ?
C9 C10 C11 C12 -0.3(9) . . . . ?
C8 C7 C12 C11 1.1(9) . . . . ?
C6 C7 C12 C11 -175.5(6) . . . . ?
C10 C11 C12 C7 0.1(9) . . . . ?
C26 C21 C22 C23 0.6(8) . . . . ?
Bi2 C21 C22 C23 -178.7(4) . . . . ?
C21 C22 C23 C24 0.1(9) . . . . ?
C22 C23 C24 C25 0.7(10) . . . . ?
C23 C24 C25 C26 -2.1(10) . . . . ?
C24 C25 C26 C21 2.8(9) . . . . ?
C24 C25 C26 C27 -179.7(6) . . . . ?
C22 C21 C26 C25 -2.1(9) . . . . ?
Bi2 C21 C26 C25 177.3(4) . . . . ?
C22 C21 C26 C27 -179.5(5) . . . . ?
Bi2 C21 C26 C27 -0.2(7) . . . . ?
C25 C26 C27 C28 131.2(6) . . . . ?
C21 C26 C27 C28 -51.4(8) . . . . ?
C25 C26 C27 C32 -50.9(8) . . . . ?
C21 C26 C27 C32 126.5(6) . . . . ?
C32 C27 C28 C29 -5.3(9) . . . . ?
C26 C27 C28 C29 172.7(6) . . . . ?
C27 C28 C29 C30 3.4(9) . . . . ?
C28 C29 C30 C31 -0.2(10) . . . . ?
C29 C30 C31 C32 -1.2(10) . . . . ?
C30 C31 C32 C27 -0.7(9) . . . . ?
C28 C27 C32 C31 3.9(9) . . . . ?
C26 C27 C32 C31 -174.1(6) . . . . ?

_refine_diff_density_max         1.686
_refine_diff_density_min         -1.828
_refine_diff_density_rms         0.193

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AP379-2
_database_code_depnum_ccdc_archive 'CCDC 1950690'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2020-03-16 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Bi Br2'
_chemical_formula_sum            'C12 H9 Bi Br2'
_chemical_formula_weight         521.99

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'

_cell_length_a                   7.5467(5)
_cell_length_b                   9.2977(5)
_cell_length_c                   18.6372(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.936(6)
_cell_angle_gamma                90
_cell_volume                     1302.87(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(7)
_cell_measurement_reflns_used    2461
_cell_measurement_theta_min      3.3160
_cell_measurement_theta_max      27.6550

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.661
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    19.632
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.29748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(7)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8056
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.337
_diffrn_reflns_theta_max         25.240
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2349
_reflns_number_gt                1878
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.9693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2349
_refine_ls_number_parameters     192
_refine_ls_number_restraints     194
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.150(3) 0.113(2) 0.1945(9) 0.035(4) Uani 0.59(3) 1 d G . P A 1
C2 C 0.301(3) 0.035(2) 0.2180(9) 0.040(4) Uani 0.59(3) 1 d G . P A 1
H2 H 0.340685 0.034411 0.266663 0.048 Uiso 0.59(3) 1 calc R U P A 1
C3 C 0.392(2) -0.041(2) 0.1689(11) 0.050(5) Uani 0.59(3) 1 d G . P A 1
H3 H 0.493509 -0.093231 0.184582 0.060 Uiso 0.59(3) 1 calc R U P A 1
C4 C 0.333(2) -0.040(2) 0.0962(10) 0.050(5) Uani 0.59(3) 1 d G . P A 1
H4 H 0.394032 -0.090815 0.063287 0.060 Uiso 0.59(3) 1 calc R U P A 1
C5 C 0.182(2) 0.038(2) 0.0727(9) 0.055(5) Uani 0.59(3) 1 d G . P A 1
H5 H 0.141729 0.039244 0.024073 0.066 Uiso 0.59(3) 1 calc R U P A 1
C6 C 0.090(3) 0.115(2) 0.1219(9) 0.038(3) Uani 0.59(3) 1 d G . P A 1
Br1 Br 0.17314(13) 0.48987(11) 0.18928(5) 0.0434(3) Uani 1 1 d . . . B 1
C7 C -0.075(2) 0.192(2) 0.0968(9) 0.037(3) Uani 0.59(3) 1 d G . P A 1
C8 C -0.076(3) 0.2882(19) 0.0396(8) 0.039(4) Uani 0.59(3) 1 d G . P A 1
H8 H 0.026951 0.301749 0.016067 0.047 Uiso 0.59(3) 1 calc R U P A 1
C9 C -0.230(3) 0.3638(17) 0.0174(7) 0.051(5) Uani 0.59(3) 1 d G . P A 1
H9 H -0.230094 0.427867 -0.020884 0.061 Uiso 0.59(3) 1 calc R U P A 1
C10 C -0.383(2) 0.3435(18) 0.0526(10) 0.054(5) Uani 0.59(3) 1 d G . P A 1
H10 H -0.485877 0.394046 0.037754 0.065 Uiso 0.59(3) 1 calc R U P A 1
C11 C -0.382(2) 0.248(2) 0.1098(11) 0.051(5) Uani 0.59(3) 1 d G . P A 1
H11 H -0.484617 0.234109 0.133344 0.062 Uiso 0.59(3) 1 calc R U P A 1
C12 C -0.228(2) 0.172(2) 0.1320(10) 0.041(4) Uani 0.59(3) 1 d G . P A 1
H12 H -0.227573 0.107989 0.170296 0.050 Uiso 0.59(3) 1 calc R U P A 1
Bi1 Bi -0.00648(5) 0.24055(4) 0.26890(2) 0.03596(19) Uani 1 1 d . . . . .
C107 C -0.048(3) 0.165(3) 0.0936(14) 0.038(5) Uani 0.41(3) 1 d G . P A 2
C108 C -0.010(3) 0.265(3) 0.0413(13) 0.043(6) Uani 0.41(3) 1 d G . P A 2
H108 H 0.103669 0.270408 0.026140 0.052 Uiso 0.41(3) 1 calc R U P A 2
C109 C -0.143(4) 0.355(2) 0.0117(12) 0.053(7) Uani 0.41(3) 1 d G . P A 2
H109 H -0.118492 0.422109 -0.023259 0.064 Uiso 0.41(3) 1 calc R U P A 2
C110 C -0.314(4) 0.347(3) 0.0344(14) 0.055(7) Uani 0.41(3) 1 d G . P A 2
H110 H -0.402897 0.407634 0.014573 0.066 Uiso 0.41(3) 1 calc R U P A 2
C111 C -0.351(3) 0.247(3) 0.0866(17) 0.051(7) Uani 0.41(3) 1 d G . P A 2
H111 H -0.465142 0.241458 0.101804 0.061 Uiso 0.41(3) 1 calc R U P A 2
C112 C -0.218(4) 0.156(3) 0.1162(16) 0.041(4) Uani 0.41(3) 1 d G . P A 2
H112 H -0.242983 0.089756 0.151205 0.050 Uiso 0.41(3) 1 calc R U P A 2
Br2 Br 0.22976(18) 0.23597(13) 0.37971(6) 0.0608(4) Uani 1 1 d . . . C 2
C106 C 0.105(3) 0.081(3) 0.1307(12) 0.034(4) Uani 0.41(3) 1 d G . P A 2
C105 C 0.204(3) -0.007(3) 0.0891(10) 0.040(6) Uani 0.41(3) 1 d G . P A 2
H105 H 0.173054 -0.016376 0.040015 0.049 Uiso 0.41(3) 1 calc R U P A 2
C104 C 0.351(3) -0.081(3) 0.1210(12) 0.041(6) Uani 0.41(3) 1 d G . P A 2
H104 H 0.417121 -0.139928 0.093258 0.049 Uiso 0.41(3) 1 calc R U P A 2
C103 C 0.398(3) -0.067(3) 0.1945(12) 0.033(5) Uani 0.41(3) 1 d G . P A 2
H103 H 0.495563 -0.116243 0.215802 0.039 Uiso 0.41(3) 1 calc R U P A 2
C102 C 0.298(4) 0.021(3) 0.2360(10) 0.040(7) Uani 0.41(3) 1 d G . P A 2
H102 H 0.329939 0.030993 0.285104 0.048 Uiso 0.41(3) 1 calc R U P A 2
C101 C 0.152(4) 0.096(3) 0.2041(12) 0.031(6) Uani 0.41(3) 1 d G . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 Bi1 2.234(11) . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.479(15) . ?
Br1 Bi1 2.7911(10) 2 ?
Br1 Bi1 3.1240(10) . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9300 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
Bi1 C101 2.228(17) . ?
Bi1 Br2 2.6099(13) . ?
C107 C108 1.3900 . ?
C107 C112 1.3900 . ?
C107 C106 1.51(2) . ?
C108 C109 1.3900 . ?
C108 H108 0.9300 . ?
C109 C110 1.3900 . ?
C109 H109 0.9300 . ?
C110 C111 1.3900 . ?
C110 H110 0.9300 . ?
C111 C112 1.3900 . ?
C111 H111 0.9300 . ?
C112 H112 0.9300 . ?
C106 C105 1.3900 . ?
C106 C101 1.3900 . ?
C105 C104 1.3900 . ?
C105 H105 0.9300 . ?
C104 C103 1.3900 . ?
C104 H104 0.9300 . ?
C103 C102 1.3900 . ?
C103 H103 0.9300 . ?
C102 C101 1.3900 . ?
C102 H102 0.9300 . ?

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
C2 C1 C6 120.0 . . ?
C2 C1 Bi1 122.9(8) . . ?
C6 C1 Bi1 117.1(8) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 119.6(11) . . ?
C1 C6 C7 120.3(11) . . ?
Bi1 Br1 Bi1 105.23(3) 2 . ?
C8 C7 C12 120.0 . . ?
C8 C7 C6 120.2(11) . . ?
C12 C7 C6 119.8(11) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C101 Bi1 Br2 93.2(7) . . ?
C1 Bi1 Br1 90.3(7) . 2_545 ?
C1 Bi1 Br1 79.9(7) . . ?
Br1 Bi1 Br1 167.59(2) 2_545 . ?
C108 C107 C112 120.0 . . ?
C108 C107 C106 118.1(17) . . ?
C112 C107 C106 121.4(16) . . ?
C107 C108 C109 120.0 . . ?
C107 C108 H108 120.0 . . ?
C109 C108 H108 120.0 . . ?
C108 C109 C110 120.0 . . ?
C108 C109 H109 120.0 . . ?
C110 C109 H109 120.0 . . ?
C111 C110 C109 120.0 . . ?
C111 C110 H110 120.0 . . ?
C109 C110 H110 120.0 . . ?
C110 C111 C112 120.0 . . ?
C110 C111 H111 120.0 . . ?
C112 C111 H111 120.0 . . ?
C111 C112 C107 120.0 . . ?
C111 C112 H112 120.0 . . ?
C107 C112 H112 120.0 . . ?
C105 C106 C101 120.0 . . ?
C105 C106 C107 118.5(16) . . ?
C101 C106 C107 121.5(16) . . ?
C106 C105 C104 120.0 . . ?
C106 C105 H105 120.0 . . ?
C104 C105 H105 120.0 . . ?
C103 C104 C105 120.0 . . ?
C103 C104 H104 120.0 . . ?
C105 C104 H104 120.0 . . ?
C104 C103 C102 120.0 . . ?
C104 C103 H103 120.0 . . ?
C102 C103 H103 120.0 . . ?
C103 C102 C101 120.0 . . ?
C103 C102 H102 120.0 . . ?
C101 C102 H102 120.0 . . ?
C102 C101 C106 120.0 . . ?
C102 C101 Bi1 120.8(12) . . ?
C106 C101 Bi1 119.2(12) . . ?

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
C6 C1 C2 C3 0.0 . . . . ?
Bi1 C1 C2 C3 -179.7(16) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 -177.5(17) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
Bi1 C1 C6 C5 179.7(16) . . . . ?
C2 C1 C6 C7 177.4(17) . . . . ?
Bi1 C1 C6 C7 -2.8(16) . . . . ?
C5 C6 C7 C8 -52.5(19) . . . . ?
C1 C6 C7 C8 130.1(13) . . . . ?
C5 C6 C7 C12 129.2(12) . . . . ?
C1 C6 C7 C12 -48.3(17) . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
C6 C7 C8 C9 -178.3(17) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C6 C7 C12 C11 178.3(17) . . . . ?
C112 C107 C108 C109 0.0 . . . . ?
C106 C107 C108 C109 -173(2) . . . . ?
C107 C108 C109 C110 0.0 . . . . ?
C108 C109 C110 C111 0.0 . . . . ?
C109 C110 C111 C112 0.0 . . . . ?
C110 C111 C112 C107 0.0 . . . . ?
C108 C107 C112 C111 0.0 . . . . ?
C106 C107 C112 C111 172(3) . . . . ?
C108 C107 C106 C105 -61(3) . . . . ?
C112 C107 C106 C105 126.2(19) . . . . ?
C108 C107 C106 C101 116.1(18) . . . . ?
C112 C107 C106 C101 -56(2) . . . . ?
C101 C106 C105 C104 0.0 . . . . ?
C107 C106 C105 C104 177(2) . . . . ?
C106 C105 C104 C103 0.0 . . . . ?
C105 C104 C103 C102 0.0 . . . . ?
C104 C103 C102 C101 0.0 . . . . ?
C103 C102 C101 C106 0.0 . . . . ?
C103 C102 C101 Bi1 -179(2) . . . . ?
C105 C106 C101 C102 0.0 . . . . ?
C107 C106 C101 C102 -177(2) . . . . ?
C105 C106 C101 Bi1 179(2) . . . . ?
C107 C106 C101 Bi1 2(2) . . . . ?

_refine_diff_density_max         1.490
_refine_diff_density_min         -1.090
_refine_diff_density_rms         0.205

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1948650'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2020-04-03 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H27 Sb'
_chemical_formula_weight         581.32

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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0086(7)
_cell_length_b                   20.2781(14)
_cell_length_c                   13.7772(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.442(2)
_cell_angle_gamma                90
_cell_volume                     2636.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9791
_cell_measurement_theta_min      2.9488
_cell_measurement_theta_max      25.6084

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.070
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.740

_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.74

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'bruker venture d8'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27264
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.222
_diffrn_reflns_theta_max         25.615
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4957
_reflns_number_gt                4650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2017.3-0'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²+2.0195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0051(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4957
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_gt          0.0469
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

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 0.59815(17) 0.63800(8) 0.37379(12) 0.0136(3) Uani 1 1 d . . . . .
C2 C 0.51905(18) 0.69591(8) 0.34765(13) 0.0161(3) Uani 1 1 d . . . . .
H00V H 0.4925 0.7119 0.2790 0.019 Uiso 1 1 calc R U . . .
C3 C 0.47841(18) 0.73058(8) 0.42005(14) 0.0180(3) Uani 1 1 d . . . . .
H00P H 0.4231 0.7695 0.4005 0.022 Uiso 1 1 calc R U . . .
C4 C 0.51840(19) 0.70851(9) 0.52071(14) 0.0205(4) Uani 1 1 d . . . . .
H009 H 0.4906 0.7321 0.5705 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5994(2) 0.65176(9) 0.54838(13) 0.0207(4) Uani 1 1 d . . . . .
H00H H 0.6278 0.6369 0.6177 0.025 Uiso 1 1 calc R U . . .
C6 C 0.63999(17) 0.61612(8) 0.47623(13) 0.0152(3) Uani 1 1 d . . . . .
C7 C 0.72948(18) 0.55609(8) 0.51180(12) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.86902(19) 0.56268(9) 0.57697(13) 0.0191(4) Uani 1 1 d . . . . .
H00U H 0.9070 0.6054 0.5969 0.023 Uiso 1 1 calc R U . . .
C9 C 0.9532(2) 0.50775(9) 0.61322(14) 0.0224(4) Uani 1 1 d . . . . .
H00W H 1.0485 0.5130 0.6571 0.027 Uiso 1 1 calc R U . . .
C10 C 0.8984(2) 0.44518(9) 0.58534(14) 0.0228(4) Uani 1 1 d . . . . .
H00M H 0.9559 0.4074 0.6100 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7596(2) 0.43789(9) 0.52138(15) 0.0249(4) Uani 1 1 d . . . . .
H00A H 0.7216 0.3950 0.5029 0.030 Uiso 1 1 calc R U . . .
C12 C 0.6754(2) 0.49291(9) 0.48400(14) 0.0210(4) Uani 1 1 d . . . . .
H00N H 0.5806 0.4874 0.4393 0.025 Uiso 1 1 calc R U . . .
C13 C 0.50704(17) 0.51345(8) 0.21961(12) 0.0137(3) Uani 1 1 d . . . . .
C14 C 0.38124(18) 0.52103(8) 0.24154(13) 0.0163(3) Uani 1 1 d . . . . .
H00L H 0.3646 0.5609 0.2719 0.020 Uiso 1 1 calc R U . . .
C15 C 0.28019(19) 0.47128(9) 0.21967(13) 0.0191(4) Uani 1 1 d . . . . .
H00K H 0.1948 0.4772 0.2345 0.023 Uiso 1 1 calc R U . . .
C16 C 0.30465(19) 0.41293(8) 0.17604(14) 0.0201(4) Uani 1 1 d . . . . .
H00R H 0.2361 0.3786 0.1613 0.024 Uiso 1 1 calc R U . . .
C17 C 0.42864(19) 0.40439(8) 0.15382(14) 0.0183(4) Uani 1 1 d . . . . .
H00D H 0.4444 0.3643 0.1236 0.022 Uiso 1 1 calc R U . . .
C18 C 0.53075(18) 0.45420(8) 0.17541(12) 0.0144(3) Uani 1 1 d . . . . .
C19 C 0.66323(18) 0.44209(8) 0.15146(12) 0.0151(3) Uani 1 1 d . . . . .
C20 C 0.75472(19) 0.39112(9) 0.20065(14) 0.0204(4) Uani 1 1 d . . . . .
H002 H 0.7343 0.3655 0.2517 0.024 Uiso 1 1 calc R U . . .
C21 C 0.8751(2) 0.37759(9) 0.17553(15) 0.0250(4) Uani 1 1 d . . . . .
H00B H 0.9365 0.3428 0.2093 0.030 Uiso 1 1 calc R U . . .
C22 C 0.9060(2) 0.41479(9) 0.10130(15) 0.0248(4) Uani 1 1 d . . . . .
H00I H 0.9878 0.4051 0.0835 0.030 Uiso 1 1 calc R U . . .
C23 C 0.8178(2) 0.46591(9) 0.05334(14) 0.0224(4) Uani 1 1 d . . . . .
H00S H 0.8398 0.4918 0.0032 0.027 Uiso 1 1 calc R U . . .
C24 C 0.69662(19) 0.47985(9) 0.07800(13) 0.0182(3) Uani 1 1 d . . . . .
H00E H 0.6365 0.5152 0.0447 0.022 Uiso 1 1 calc R U . . .
C25 C 0.58654(18) 0.65481(8) 0.14282(12) 0.0140(3) Uani 1 1 d . . . . .
C26 C 0.44060(18) 0.66274(9) 0.09533(13) 0.0171(3) Uani 1 1 d . . . . .
H00O H 0.3777 0.6314 0.1079 0.021 Uiso 1 1 calc R U . . .
C27 C 0.38572(19) 0.71543(9) 0.03020(13) 0.0200(4) Uani 1 1 d . . . . .
H00T H 0.2862 0.7201 -0.0015 0.024 Uiso 1 1 calc R U . . .
C28 C 0.4769(2) 0.76138(9) 0.01156(14) 0.0220(4) Uani 1 1 d . . . . .
H00Q H 0.4399 0.7984 -0.0311 0.026 Uiso 1 1 calc R U . . .
C29 C 0.62256(19) 0.75317(9) 0.05543(14) 0.0207(4) Uani 1 1 d . . . . .
H00F H 0.6847 0.7842 0.0412 0.025 Uiso 1 1 calc R U . . .
C30 C 0.67847(18) 0.69979(8) 0.12022(12) 0.0152(3) Uani 1 1 d . . . . .
C31 C 0.83549(18) 0.69040(8) 0.16176(13) 0.0148(3) Uani 1 1 d . . . . .
C32 C 0.92182(19) 0.72897(8) 0.24134(13) 0.0184(4) Uani 1 1 d . . . . .
H00X H 0.8808 0.7618 0.2717 0.022 Uiso 1 1 calc R U . . .
C33 C 1.06764(19) 0.71989(9) 0.27686(14) 0.0207(4) Uani 1 1 d . . . . .
H011 H 1.1256 0.7465 0.3314 0.025 Uiso 1 1 calc R U . . .
C34 C 1.12903(19) 0.67235(9) 0.23323(14) 0.0194(4) Uani 1 1 d . . . . .
H010 H 1.2289 0.6667 0.2571 0.023 Uiso 1 1 calc R U . . .
C35 C 1.0442(2) 0.63321(9) 0.15484(14) 0.0212(4) Uani 1 1 d . . . . .
H00Y H 1.0857 0.6000 0.1253 0.025 Uiso 1 1 calc R U . . .
C36 C 0.89825(19) 0.64226(8) 0.11902(14) 0.0186(4) Uani 1 1 d . . . . .
H00Z H 0.8406 0.6153 0.0648 0.022 Uiso 1 1 calc R U . . .
Sb1 Sb 0.67608(2) 0.58520(2) 0.26648(2) 0.01139(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.395(2) . ?
C1 C6 1.404(2) . ?
C1 Sb1 2.1698(16) . ?
C2 C3 1.387(2) . ?
C2 H00V 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H00P 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H009 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H00H 0.9500 . ?
C6 C7 1.494(2) . ?
C7 C8 1.393(3) . ?
C7 C12 1.394(2) . ?
C8 C9 1.386(3) . ?
C8 H00U 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H00W 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H00M 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H00A 0.9500 . ?
C12 H00N 0.9500 . ?
C13 C14 1.398(2) . ?
C13 C18 1.403(2) . ?
C13 Sb1 2.1608(16) . ?
C14 C15 1.389(2) . ?
C14 H00L 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H00K 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H00R 0.9500 . ?
C17 C18 1.397(2) . ?
C17 H00D 0.9500 . ?
C18 C19 1.489(2) . ?
C19 C24 1.396(2) . ?
C19 C20 1.397(2) . ?
C20 C21 1.387(3) . ?
C20 H002 0.9500 . ?
C21 C22 1.386(3) . ?
C21 H00B 0.9500 . ?
C22 C23 1.379(3) . ?
C22 H00I 0.9500 . ?
C23 C24 1.393(2) . ?
C23 H00S 0.9500 . ?
C24 H00E 0.9500 . ?
C25 C26 1.397(2) . ?
C25 C30 1.402(2) . ?
C25 Sb1 2.1637(16) . ?
C26 C27 1.386(2) . ?
C26 H00O 0.9500 . ?
C27 C28 1.387(3) . ?
C27 H00T 0.9500 . ?
C28 C29 1.390(3) . ?
C28 H00Q 0.9500 . ?
C29 C30 1.396(2) . ?
C29 H00F 0.9500 . ?
C30 C31 1.495(2) . ?
C31 C32 1.389(2) . ?
C31 C36 1.393(2) . ?
C32 C33 1.388(3) . ?
C32 H00X 0.9500 . ?
C33 C34 1.383(3) . ?
C33 H011 0.9500 . ?
C34 C35 1.381(3) . ?
C34 H010 0.9500 . ?
C35 C36 1.390(3) . ?
C35 H00Y 0.9500 . ?
C36 H00Z 0.9500 . ?

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
C2 C1 C6 118.64(15) . . ?
C2 C1 Sb1 122.77(12) . . ?
C6 C1 Sb1 118.33(12) . . ?
C3 C2 C1 121.20(16) . . ?
C3 C2 H00V 119.4 . . ?
C1 C2 H00V 119.4 . . ?
C4 C3 C2 120.03(16) . . ?
C4 C3 H00P 120.0 . . ?
C2 C3 H00P 120.0 . . ?
C3 C4 C5 119.46(16) . . ?
C3 C4 H009 120.3 . . ?
C5 C4 H009 120.3 . . ?
C4 C5 C6 121.11(16) . . ?
C4 C5 H00H 119.4 . . ?
C6 C5 H00H 119.4 . . ?
C5 C6 C1 119.53(15) . . ?
C5 C6 C7 118.26(15) . . ?
C1 C6 C7 122.20(14) . . ?
C8 C7 C12 118.66(16) . . ?
C8 C7 C6 119.76(16) . . ?
C12 C7 C6 121.55(16) . . ?
C9 C8 C7 120.96(17) . . ?
C9 C8 H00U 119.5 . . ?
C7 C8 H00U 119.5 . . ?
C10 C9 C8 119.93(18) . . ?
C10 C9 H00W 120.0 . . ?
C8 C9 H00W 120.0 . . ?
C11 C10 C9 119.73(17) . . ?
C11 C10 H00M 120.1 . . ?
C9 C10 H00M 120.1 . . ?
C10 C11 C12 120.46(18) . . ?
C10 C11 H00A 119.8 . . ?
C12 C11 H00A 119.8 . . ?
C11 C12 C7 120.25(18) . . ?
C11 C12 H00N 119.9 . . ?
C7 C12 H00N 119.9 . . ?
C14 C13 C18 118.88(15) . . ?
C14 C13 Sb1 122.24(12) . . ?
C18 C13 Sb1 118.54(12) . . ?
C15 C14 C13 121.11(16) . . ?
C15 C14 H00L 119.4 . . ?
C13 C14 H00L 119.4 . . ?
C16 C15 C14 119.57(16) . . ?
C16 C15 H00K 120.2 . . ?
C14 C15 H00K 120.2 . . ?
C17 C16 C15 120.24(16) . . ?
C17 C16 H00R 119.9 . . ?
C15 C16 H00R 119.9 . . ?
C16 C17 C18 120.58(16) . . ?
C16 C17 H00D 119.7 . . ?
C18 C17 H00D 119.7 . . ?
C17 C18 C13 119.63(15) . . ?
C17 C18 C19 118.41(15) . . ?
C13 C18 C19 121.96(15) . . ?
C24 C19 C20 118.76(16) . . ?
C24 C19 C18 121.05(15) . . ?
C20 C19 C18 120.17(15) . . ?
C21 C20 C19 120.57(17) . . ?
C21 C20 H002 119.7 . . ?
C19 C20 H002 119.7 . . ?
C22 C21 C20 120.15(17) . . ?
C22 C21 H00B 119.9 . . ?
C20 C21 H00B 119.9 . . ?
C23 C22 C21 119.84(17) . . ?
C23 C22 H00I 120.1 . . ?
C21 C22 H00I 120.1 . . ?
C22 C23 C24 120.42(17) . . ?
C22 C23 H00S 119.8 . . ?
C24 C23 H00S 119.8 . . ?
C23 C24 C19 120.24(17) . . ?
C23 C24 H00E 119.9 . . ?
C19 C24 H00E 119.9 . . ?
C26 C25 C30 118.84(15) . . ?
C26 C25 Sb1 122.57(12) . . ?
C30 C25 Sb1 117.96(12) . . ?
C27 C26 C25 121.28(16) . . ?
C27 C26 H00O 119.4 . . ?
C25 C26 H00O 119.4 . . ?
C26 C27 C28 119.64(17) . . ?
C26 C27 H00T 120.2 . . ?
C28 C27 H00T 120.2 . . ?
C27 C28 C29 119.92(16) . . ?
C27 C28 H00Q 120.0 . . ?
C29 C28 H00Q 120.0 . . ?
C28 C29 C30 120.67(16) . . ?
C28 C29 H00F 119.7 . . ?
C30 C29 H00F 119.7 . . ?
C29 C30 C25 119.56(16) . . ?
C29 C30 C31 119.34(15) . . ?
C25 C30 C31 121.07(15) . . ?
C32 C31 C36 118.60(16) . . ?
C32 C31 C30 121.93(15) . . ?
C36 C31 C30 119.47(15) . . ?
C33 C32 C31 120.54(16) . . ?
C33 C32 H00X 119.7 . . ?
C31 C32 H00X 119.7 . . ?
C34 C33 C32 120.40(17) . . ?
C34 C33 H011 119.8 . . ?
C32 C33 H011 119.8 . . ?
C35 C34 C33 119.60(17) . . ?
C35 C34 H010 120.2 . . ?
C33 C34 H010 120.2 . . ?
C34 C35 C36 120.11(16) . . ?
C34 C35 H00Y 119.9 . . ?
C36 C35 H00Y 119.9 . . ?
C35 C36 C31 120.74(16) . . ?
C35 C36 H00Z 119.6 . . ?
C31 C36 H00Z 119.6 . . ?
C13 Sb1 C25 97.25(6) . . ?
C13 Sb1 C1 96.46(6) . . ?
C25 Sb1 C1 93.78(6) . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AP379Kr
_database_code_depnum_ccdc_archive 'CCDC 1950689'
loop_
_audit_author_name
_audit_author_address
'Marcus Korb'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2020-03-16 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Bi Br'
_chemical_formula_sum            'C24 H18 Bi Br'
_chemical_formula_weight         595.27

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9115(7)
_cell_length_b                   15.7922(9)
_cell_length_c                   13.3369(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.717(7)
_cell_angle_gamma                90
_cell_volume                     1988.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    115.7(10)
_cell_measurement_reflns_used    2726
_cell_measurement_theta_min      3.3680
_cell_measurement_theta_max      27.6480

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    10.880
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.39371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      115.7(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8769
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.432
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.498
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3653
_reflns_number_gt                2901
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3653
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.2005(6) -0.1311(3) 0.7247(4) 0.0231(13) Uani 1 1 d . . . . .
C2 C 0.2344(7) -0.1604(3) 0.6375(4) 0.0322(15) Uani 1 1 d . . . . .
H2 H 0.291006 -0.127512 0.608557 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1849(8) -0.2385(4) 0.5926(4) 0.0404(18) Uani 1 1 d . . . . .
H3 H 0.209762 -0.257681 0.534679 0.048 Uiso 1 1 calc R U . . .
C4 C 0.1007(7) -0.2864(4) 0.6328(5) 0.0402(17) Uani 1 1 d . . . . .
H4 H 0.067018 -0.338085 0.601654 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0640(7) -0.2594(3) 0.7202(5) 0.0343(15) Uani 1 1 d . . . . .
H5 H 0.005404 -0.292596 0.746875 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1160(6) -0.1811(3) 0.7684(4) 0.0260(13) Uani 1 1 d . . . . .
C7 C 0.0800(6) -0.1556(3) 0.8640(4) 0.0238(13) Uani 1 1 d . . . . .
C8 C 0.1844(7) -0.1346(3) 0.9560(4) 0.0274(14) Uani 1 1 d . . . . .
H8 H 0.278790 -0.137010 0.957515 0.033 Uiso 1 1 calc R U . . .
C9 C 0.1529(7) -0.1103(3) 1.0456(4) 0.0319(15) Uani 1 1 d . . . . .
H9 H 0.225130 -0.095734 1.106056 0.038 Uiso 1 1 calc R U . . .
C10 C 0.0135(8) -0.1075(4) 1.0450(5) 0.0391(17) Uani 1 1 d . . . . .
H10 H -0.008462 -0.091175 1.105236 0.047 Uiso 1 1 calc R U . . .
C11 C -0.0921(8) -0.1288(4) 0.9559(6) 0.0440(18) Uani 1 1 d . . . . .
H11 H -0.185985 -0.127667 0.955775 0.053 Uiso 1 1 calc R U . . .
C12 C -0.0594(7) -0.1525(3) 0.8647(5) 0.0352(15) Uani 1 1 d . . . . .
H12 H -0.132039 -0.166312 0.804106 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2999(6) 0.0535(3) 0.6471(4) 0.0188(12) Uani 1 1 d . . . . .
C14 C 0.4249(6) 0.0475(3) 0.6193(4) 0.0257(13) Uani 1 1 d . . . . .
H14 H 0.496473 0.011011 0.656249 0.031 Uiso 1 1 calc R U . . .
C15 C 0.4425(6) 0.0947(3) 0.5384(4) 0.0257(13) Uani 1 1 d . . . . .
H15 H 0.525736 0.090020 0.520438 0.031 Uiso 1 1 calc R U . . .
C16 C 0.3364(7) 0.1500(3) 0.4827(4) 0.0269(14) Uani 1 1 d . . . . .
H16 H 0.348193 0.182235 0.427614 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2122(6) 0.1561(3) 0.5110(4) 0.0259(13) Uani 1 1 d . . . . .
H17 H 0.141075 0.193082 0.474659 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1937(6) 0.1080(3) 0.5924(4) 0.0189(12) Uani 1 1 d . . . . .
C19 C 0.0619(5) 0.1172(3) 0.6238(4) 0.0176(11) Uani 1 1 d . . . . .
C20 C 0.0273(6) 0.1960(3) 0.6566(4) 0.0252(13) Uani 1 1 d . . . . .
H20 H 0.085891 0.242437 0.658802 0.030 Uiso 1 1 calc R U . . .
C21 C -0.0955(6) 0.2048(4) 0.6859(4) 0.0289(14) Uani 1 1 d . . . . .
H21 H -0.118192 0.257010 0.708780 0.035 Uiso 1 1 calc R U . . .
C22 C -0.1838(6) 0.1360(4) 0.6812(4) 0.0305(14) Uani 1 1 d . . . . .
H22 H -0.266573 0.142563 0.699530 0.037 Uiso 1 1 calc R U . . .
C23 C -0.1501(6) 0.0586(4) 0.6498(4) 0.0290(14) Uani 1 1 d . . . . .
H23 H -0.209269 0.012456 0.647317 0.035 Uiso 1 1 calc R U . . .
C24 C -0.0269(6) 0.0492(3) 0.6215(4) 0.0257(13) Uani 1 1 d . . . . .
H24 H -0.003924 -0.003671 0.600701 0.031 Uiso 1 1 calc R U . . .
Br1 Br 0.53621(7) -0.05067(4) 0.87154(5) 0.03598(16) Uani 1 1 d . . . . .
Bi1 Bi 0.26773(2) -0.00276(2) 0.79335(2) 0.02067(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.385(7) . ?
C1 C6 1.400(7) . ?
C1 Bi1 2.240(5) . ?
C2 C3 1.393(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.480(7) . ?
C7 C8 1.384(8) . ?
C7 C12 1.386(8) . ?
C8 C9 1.378(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.402(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.383(7) . ?
C13 C14 1.400(7) . ?
C13 Bi1 2.252(5) . ?
C14 C15 1.366(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.496(7) . ?
C19 C24 1.383(7) . ?
C19 C20 1.396(7) . ?
C20 C21 1.395(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
Br1 Bi1 2.6557(7) . ?

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
C2 C1 C6 119.3(5) . . ?
C2 C1 Bi1 121.8(4) . . ?
C6 C1 Bi1 118.8(3) . . ?
C1 C2 C3 120.8(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.8(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.0(5) . . ?
C1 C6 C7 122.4(5) . . ?
C5 C6 C7 118.6(5) . . ?
C8 C7 C12 117.6(5) . . ?
C8 C7 C6 121.2(5) . . ?
C12 C7 C6 121.2(5) . . ?
C9 C8 C7 122.0(6) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 119.7(6) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.2(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.7(6) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C18 C13 C14 119.7(5) . . ?
C18 C13 Bi1 114.6(3) . . ?
C14 C13 Bi1 124.9(4) . . ?
C15 C14 C13 120.5(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 118.9(5) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 120.8(5) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 119.7(5) . . ?
C17 C18 C19 120.2(5) . . ?
C13 C18 C19 120.1(4) . . ?
C24 C19 C20 118.9(5) . . ?
C24 C19 C18 121.5(5) . . ?
C20 C19 C18 119.6(5) . . ?
C21 C20 C19 119.7(5) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.4(5) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.7(5) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 121.1(5) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C1 Bi1 C13 96.09(17) . . ?
C1 Bi1 Br1 92.33(14) . . ?
C13 Bi1 Br1 93.63(14) . . ?

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
C6 C1 C2 C3 0.4(9) . . . . ?
Bi1 C1 C2 C3 -176.4(5) . . . . ?
C1 C2 C3 C4 1.0(9) . . . . ?
C2 C3 C4 C5 -0.9(10) . . . . ?
C3 C4 C5 C6 -0.5(9) . . . . ?
C2 C1 C6 C5 -1.8(8) . . . . ?
Bi1 C1 C6 C5 175.1(4) . . . . ?
C2 C1 C6 C7 177.6(5) . . . . ?
Bi1 C1 C6 C7 -5.5(7) . . . . ?
C4 C5 C6 C1 1.9(8) . . . . ?
C4 C5 C6 C7 -177.5(5) . . . . ?
C1 C6 C7 C8 -54.0(7) . . . . ?
C5 C6 C7 C8 125.4(6) . . . . ?
C1 C6 C7 C12 126.5(6) . . . . ?
C5 C6 C7 C12 -54.1(7) . . . . ?
C12 C7 C8 C9 -0.9(8) . . . . ?
C6 C7 C8 C9 179.6(5) . . . . ?
C7 C8 C9 C10 0.9(8) . . . . ?
C8 C9 C10 C11 -0.1(9) . . . . ?
C9 C10 C11 C12 -0.8(9) . . . . ?
C8 C7 C12 C11 0.0(8) . . . . ?
C6 C7 C12 C11 179.5(5) . . . . ?
C10 C11 C12 C7 0.8(9) . . . . ?
C18 C13 C14 C15 -0.2(8) . . . . ?
Bi1 C13 C14 C15 -169.4(4) . . . . ?
C13 C14 C15 C16 0.3(8) . . . . ?
C14 C15 C16 C17 0.0(8) . . . . ?
C15 C16 C17 C18 -0.4(8) . . . . ?
C16 C17 C18 C13 0.6(8) . . . . ?
C16 C17 C18 C19 178.2(5) . . . . ?
C14 C13 C18 C17 -0.2(8) . . . . ?
Bi1 C13 C18 C17 170.1(4) . . . . ?
C14 C13 C18 C19 -177.8(4) . . . . ?
Bi1 C13 C18 C19 -7.5(6) . . . . ?
C17 C18 C19 C24 121.3(6) . . . . ?
C13 C18 C19 C24 -61.1(7) . . . . ?
C17 C18 C19 C20 -58.9(7) . . . . ?
C13 C18 C19 C20 118.7(5) . . . . ?
C24 C19 C20 C21 -0.2(8) . . . . ?
C18 C19 C20 C21 -180.0(5) . . . . ?
C19 C20 C21 C22 -0.9(8) . . . . ?
C20 C21 C22 C23 1.3(8) . . . . ?
C21 C22 C23 C24 -0.6(8) . . . . ?
C20 C19 C24 C23 0.9(8) . . . . ?
C18 C19 C24 C23 -179.3(5) . . . . ?
C22 C23 C24 C19 -0.5(8) . . . . ?

_refine_diff_density_max         1.212
_refine_diff_density_min         -1.715
_refine_diff_density_rms         0.147

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1948648'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2020-04-03 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Bi Cl2'
_chemical_formula_sum            'C12 H9 Bi Cl2'
_chemical_formula_weight         433.07

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6237(7)
_cell_length_b                   9.0462(8)
_cell_length_c                   17.6540(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1217.52(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4660
_cell_measurement_theta_min      3.2241
_cell_measurement_theta_max      25.5754

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.363
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    14.883
_shelx_estimated_absorpt_T_min   0.318
_shelx_estimated_absorpt_T_max   0.318
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.14
_exptl_absorpt_correction_T_max  0.32

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'bruker venture d8'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5829
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.531
_diffrn_reflns_theta_max         25.574
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2249
_reflns_number_gt                2150
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2017.3-0'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.021(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2249
_refine_ls_number_parameters     138
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0457
_refine_ls_wR_factor_gt          0.0449
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_restrained_S_all      0.801
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 1.1731(9) 0.6024(7) 0.2960(5) 0.0119(14) Uani 1 1 d . U . . .
C2 C 1.3159(8) 0.6695(7) 0.2597(6) 0.0146(16) Uani 1 1 d . U . . .
H2 H 1.3363 0.6531 0.2073 0.018 Uiso 1 1 calc R U . . .
C3 C 1.4274(10) 0.7600(8) 0.3011(6) 0.0190(17) Uani 1 1 d . U . . .
H3 H 1.5246 0.8061 0.2771 0.023 Uiso 1 1 calc R U . . .
C4 C 1.3960(10) 0.7828(8) 0.3778(6) 0.0209(18) Uani 1 1 d . U . . .
H4 H 1.4717 0.8459 0.4057 0.025 Uiso 1 1 calc R U . . .
C5 C 1.2582(10) 0.7161(8) 0.4136(6) 0.0190(18) Uani 1 1 d . U . . .
H5 H 1.2402 0.7316 0.4663 0.023 Uiso 1 1 calc R U . . .
C6 C 1.1419(9) 0.6238(7) 0.3723(5) 0.0129(15) Uani 1 1 d . U . . .
C7 C 0.9967(9) 0.5490(7) 0.4115(5) 0.0142(14) Uani 1 1 d . U . . .
C8 C 1.0269(10) 0.4568(8) 0.4742(5) 0.0182(15) Uani 1 1 d . U . . .
H8 H 1.1434 0.4429 0.4919 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8926(11) 0.3868(8) 0.5103(6) 0.0231(18) Uani 1 1 d . U . . .
H9 H 0.9173 0.3257 0.5527 0.028 Uiso 1 1 calc R U . . .
C10 C 0.7215(11) 0.4027(9) 0.4865(6) 0.0226(18) Uani 1 1 d . U . . .
H10 H 0.6293 0.3547 0.5130 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6848(10) 0.4898(8) 0.4234(5) 0.0193(18) Uani 1 1 d . U . . .
H11 H 0.5679 0.4982 0.4052 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8204(10) 0.5641(7) 0.3874(5) 0.0139(17) Uani 1 1 d . U . . .
H12 H 0.7945 0.6265 0.3455 0.017 Uiso 1 1 calc R U . . .
Bi1 Bi 0.97904(3) 0.46664(3) 0.23203(2) 0.01092(11) Uani 1 1 d . U . . .
Cl1 Cl 0.8402(2) 0.72708(17) 0.19058(12) 0.0122(4) Uani 1 1 d . U . . .
Cl2 Cl 1.1626(2) 0.4564(2) 0.11643(12) 0.0169(4) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.382(13) . ?
C1 C2 1.401(10) . ?
C1 Bi1 2.230(7) . ?
C2 C3 1.388(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.420(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.471(10) . ?
C7 C8 1.405(11) . ?
C7 C12 1.416(10) . ?
C8 C9 1.361(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(12) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
Bi1 Cl2 2.476(2) . ?
Bi1 Cl1 2.6844(16) . ?
Bi1 Cl1 2.9088(18) 3_745 ?
Cl1 Bi1 2.9088(18) 3_755 ?

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
C6 C1 C2 121.2(7) . . ?
C6 C1 Bi1 117.2(5) . . ?
C2 C1 Bi1 121.5(6) . . ?
C3 C2 C1 119.4(9) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.7(8) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.2(7) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.1(9) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.4(7) . . ?
C1 C6 C7 121.6(7) . . ?
C5 C6 C7 119.9(8) . . ?
C8 C7 C12 116.8(7) . . ?
C8 C7 C6 121.4(7) . . ?
C12 C7 C6 121.9(7) . . ?
C9 C8 C7 121.4(7) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 121.4(9) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 119.5(8) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.4(7) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 121.5(7) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C1 Bi1 Cl2 93.6(2) . . ?
C1 Bi1 Cl1 85.20(19) . . ?
Cl2 Bi1 Cl1 91.77(6) . . ?
C1 Bi1 Cl1 81.85(19) . 3_745 ?
Cl2 Bi1 Cl1 95.25(6) . 3_745 ?
Cl1 Bi1 Cl1 165.61(4) . 3_745 ?
Bi1 Cl1 Bi1 109.82(7) . 3_755 ?

_refine_diff_density_max         1.000
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.139

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1948645'
loop_
_audit_author_name
_audit_author_address
'Tobias Ruffer'
;TU Chemnitz
Germany
;
_audit_update_record             
;
2020-04-03 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Bi Cl'
_chemical_formula_sum            'C24 H18 Bi Cl'
_chemical_formula_weight         550.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.9371(3)
_cell_length_b                   11.3295(4)
_cell_length_c                   17.9137(6)
_cell_angle_alpha                78.588(1)
_cell_angle_beta                 86.690(1)
_cell_angle_gamma                78.695(1)
_cell_volume                     1938.16(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    117
_cell_measurement_theta_min      4.0739
_cell_measurement_theta_max      68.0263

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    19.133
_shelx_estimated_absorpt_T_min   0.079
_shelx_estimated_absorpt_T_max   0.207
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.03
_exptl_absorpt_correction_T_max  0.21

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker venture d8'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26560
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         65.774
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             6656
_reflns_number_gt                6395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+2.2486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6656
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0521
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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 -0.15326(2) 0.67149(2) 0.01842(2) 0.01710(6) Uani 1 1 d . . . . .
Bi2 Bi 0.64176(2) 0.31570(2) 0.52691(2) 0.01865(6) Uani 1 1 d . . . . .
Cl1 Cl -0.40343(8) 0.66607(7) 0.04679(5) 0.02286(16) Uani 1 1 d . . . . .
Cl2 Cl 0.87418(8) 0.29365(8) 0.58228(5) 0.02531(17) Uani 1 1 d . . . . .
C1 C -0.1433(3) 0.7487(3) 0.12482(18) 0.0194(6) Uani 1 1 d . . . . .
C2 C -0.2426(4) 0.8494(3) 0.1357(2) 0.0224(7) Uani 1 1 d . . . . .
H2 H -0.3019 0.8922 0.0954 0.027 Uiso 1 1 calc R U . . .
C3 C -0.2555(4) 0.8879(3) 0.2056(2) 0.0268(7) Uani 1 1 d . . . . .
H3 H -0.3226 0.9574 0.2125 0.032 Uiso 1 1 calc R U . . .
C4 C -0.1706(4) 0.8247(3) 0.2648(2) 0.0272(8) Uani 1 1 d . . . . .
H4 H -0.1805 0.8499 0.3126 0.033 Uiso 1 1 calc R U . . .
C5 C -0.0713(4) 0.7249(3) 0.2542(2) 0.0264(7) Uani 1 1 d . . . . .
H5 H -0.0133 0.6822 0.2951 0.032 Uiso 1 1 calc R U . . .
C6 C -0.0544(3) 0.6853(3) 0.18398(19) 0.0210(7) Uani 1 1 d . . . . .
C7 C 0.0590(4) 0.5813(3) 0.17511(19) 0.0216(7) Uani 1 1 d . . . . .
C8 C 0.0785(4) 0.4735(3) 0.2297(2) 0.0257(7) Uani 1 1 d . . . . .
H8 H 0.0163 0.4651 0.2719 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1874(4) 0.3783(3) 0.2234(2) 0.0282(8) Uani 1 1 d . . . . .
H9 H 0.1987 0.3052 0.2609 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2800(4) 0.3895(4) 0.1624(2) 0.0302(8) Uani 1 1 d . . . . .
H10 H 0.3541 0.3239 0.1580 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2638(4) 0.4971(4) 0.1080(2) 0.0270(7) Uani 1 1 d . . . . .
H11 H 0.3278 0.5059 0.0667 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1533(4) 0.5922(3) 0.11411(19) 0.0223(7) Uani 1 1 d . . . . .
H12 H 0.1419 0.6652 0.0764 0.027 Uiso 1 1 calc R U . . .
C13 C -0.1999(3) 0.8593(3) -0.05718(18) 0.0196(6) Uani 1 1 d . . . . .
C14 C -0.3302(4) 0.9324(3) -0.0651(2) 0.0248(7) Uani 1 1 d . . . . .
H14 H -0.4075 0.9002 -0.0426 0.030 Uiso 1 1 calc R U . . .
C15 C -0.3481(4) 1.0524(4) -0.1058(2) 0.0266(7) Uani 1 1 d . . . . .
H15 H -0.4374 1.1015 -0.1115 0.032 Uiso 1 1 calc R U . . .
C16 C -0.2356(4) 1.0998(3) -0.1379(2) 0.0272(8) Uani 1 1 d . . . . .
H16 H -0.2477 1.1822 -0.1646 0.033 Uiso 1 1 calc R U . . .
C17 C -0.1050(4) 1.0280(3) -0.1314(2) 0.0237(7) Uani 1 1 d . . . . .
H17 H -0.0282 1.0611 -0.1539 0.028 Uiso 1 1 calc R U . . .
C18 C -0.0866(3) 0.9067(3) -0.09150(18) 0.0211(7) Uani 1 1 d . . . . .
C19 C 0.0537(3) 0.8290(3) -0.08563(18) 0.0204(7) Uani 1 1 d . . . . .
C20 C 0.1618(4) 0.8679(3) -0.0562(2) 0.0237(7) Uani 1 1 d . . . . .
H20 H 0.1455 0.9438 -0.0392 0.028 Uiso 1 1 calc R U . . .
C21 C 0.2927(4) 0.7959(4) -0.0518(2) 0.0294(8) Uani 1 1 d . . . . .
H21 H 0.3654 0.8228 -0.0318 0.035 Uiso 1 1 calc R U . . .
C22 C 0.3172(4) 0.6841(4) -0.0767(2) 0.0277(8) Uani 1 1 d . . . . .
H22 H 0.4066 0.6350 -0.0736 0.033 Uiso 1 1 calc R U . . .
C23 C 0.2115(4) 0.6449(3) -0.1060(2) 0.0253(7) Uani 1 1 d . . . . .
H23 H 0.2284 0.5692 -0.1233 0.030 Uiso 1 1 calc R U . . .
C24 C 0.0801(3) 0.7168(3) -0.11007(18) 0.0212(7) Uani 1 1 d . . . . .
H24 H 0.0075 0.6892 -0.1297 0.025 Uiso 1 1 calc R U . . .
C25 C 0.7400(3) 0.2128(3) 0.43556(19) 0.0214(7) Uani 1 1 d . . . . .
C26 C 0.8304(4) 0.1019(3) 0.4553(2) 0.0250(7) Uani 1 1 d . . . . .
H26 H 0.8401 0.0639 0.5074 0.030 Uiso 1 1 calc R U . . .
C27 C 0.9065(4) 0.0456(3) 0.4005(2) 0.0277(8) Uani 1 1 d . . . . .
H27 H 0.9665 -0.0311 0.4150 0.033 Uiso 1 1 calc R U . . .
C28 C 0.8947(4) 0.1022(4) 0.3241(2) 0.0300(8) Uani 1 1 d . . . . .
H28 H 0.9483 0.0651 0.2863 0.036 Uiso 1 1 calc R U . . .
C29 C 0.8046(4) 0.2127(4) 0.3033(2) 0.0286(8) Uani 1 1 d . . . . .
H29 H 0.7965 0.2507 0.2510 0.034 Uiso 1 1 calc R U . . .
C30 C 0.7255(4) 0.2687(3) 0.3584(2) 0.0233(7) Uani 1 1 d . . . . .
C31 C 0.6247(4) 0.3853(3) 0.33320(19) 0.0219(7) Uani 1 1 d . . . . .
C32 C 0.6675(4) 0.4850(4) 0.2854(2) 0.0282(8) Uani 1 1 d . . . . .
H32 H 0.7609 0.4790 0.2693 0.034 Uiso 1 1 calc R U . . .
C33 C 0.5744(5) 0.5930(4) 0.2614(2) 0.0325(8) Uani 1 1 d . . . . .
H33 H 0.6045 0.6608 0.2296 0.039 Uiso 1 1 calc R U . . .
C34 C 0.4368(4) 0.6016(3) 0.2840(2) 0.0313(8) Uani 1 1 d . . . . .
H34 H 0.3728 0.6751 0.2675 0.038 Uiso 1 1 calc R U . . .
C35 C 0.3934(4) 0.5022(4) 0.3306(2) 0.0276(8) Uani 1 1 d . . . . .
H35 H 0.2996 0.5076 0.3457 0.033 Uiso 1 1 calc R U . . .
C36 C 0.4870(4) 0.3948(3) 0.35527(19) 0.0238(7) Uani 1 1 d . . . . .
H36 H 0.4568 0.3274 0.3874 0.029 Uiso 1 1 calc R U . . .
C37 C 0.6003(4) 0.1448(3) 0.60677(18) 0.0210(7) Uani 1 1 d . . . . .
C38 C 0.6944(4) 0.0733(3) 0.6598(2) 0.0247(7) Uani 1 1 d . . . . .
H38 H 0.7779 0.0989 0.6660 0.030 Uiso 1 1 calc R U . . .
C39 C 0.6669(4) -0.0356(3) 0.7038(2) 0.0272(7) Uani 1 1 d . . . . .
H39 H 0.7300 -0.0829 0.7412 0.033 Uiso 1 1 calc R U . . .
C40 C 0.5462(4) -0.0745(3) 0.6927(2) 0.0290(8) Uani 1 1 d . . . . .
H40 H 0.5287 -0.1504 0.7210 0.035 Uiso 1 1 calc R U . . .
C41 C 0.4516(4) -0.0027(3) 0.6405(2) 0.0250(7) Uani 1 1 d . . . . .
H41 H 0.3695 -0.0300 0.6333 0.030 Uiso 1 1 calc R U . . .
C42 C 0.4751(4) 0.1087(3) 0.59834(19) 0.0217(7) Uani 1 1 d . . . . .
C43 C 0.3674(3) 0.1901(3) 0.54779(19) 0.0218(7) Uani 1 1 d . . . . .
C44 C 0.3127(4) 0.1483(3) 0.4897(2) 0.0247(7) Uani 1 1 d . . . . .
H44 H 0.3478 0.0682 0.4804 0.030 Uiso 1 1 calc R U . . .
C45 C 0.2068(4) 0.2240(4) 0.4456(2) 0.0286(8) Uani 1 1 d . . . . .
H45 H 0.1698 0.1954 0.4064 0.034 Uiso 1 1 calc R U . . .
C46 C 0.1553(4) 0.3415(4) 0.4588(2) 0.0314(8) Uani 1 1 d . . . . .
H46 H 0.0831 0.3928 0.4286 0.038 Uiso 1 1 calc R U . . .
C47 C 0.2086(4) 0.3835(3) 0.5155(2) 0.0276(8) Uani 1 1 d . . . . .
H47 H 0.1731 0.4639 0.5242 0.033 Uiso 1 1 calc R U . . .
C48 C 0.3145(4) 0.3088(3) 0.5602(2) 0.0235(7) Uani 1 1 d . . . . .
H48 H 0.3509 0.3385 0.5992 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C13 2.263(3) . ?
Bi1 C1 2.264(3) . ?
Bi1 Cl1 2.5187(8) . ?
Bi2 C37 2.261(3) . ?
Bi2 C25 2.262(3) . ?
Bi2 Cl2 2.5142(8) . ?
C1 C2 1.392(5) . ?
C1 C6 1.406(5) . ?
C2 C3 1.397(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.488(5) . ?
C7 C8 1.394(5) . ?
C7 C12 1.400(5) . ?
C8 C9 1.386(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.392(5) . ?
C13 C18 1.400(5) . ?
C14 C15 1.392(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.400(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.493(5) . ?
C19 C24 1.397(5) . ?
C19 C20 1.402(5) . ?
C20 C21 1.390(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.388(5) . ?
C25 C30 1.405(5) . ?
C26 C27 1.384(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.393(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.387(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.400(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.500(5) . ?
C31 C36 1.392(5) . ?
C31 C32 1.397(5) . ?
C32 C33 1.390(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.394(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.389(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.391(5) . ?
C37 C42 1.408(5) . ?
C38 C39 1.393(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.394(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.387(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.391(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.487(5) . ?
C43 C48 1.401(5) . ?
C43 C44 1.401(5) . ?
C44 C45 1.394(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.390(6) . ?
C45 H45 0.9500 . ?
C46 C47 1.375(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.395(5) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?

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 Bi1 C1 93.30(12) . . ?
C13 Bi1 Cl1 92.89(9) . . ?
C1 Bi1 Cl1 89.64(8) . . ?
C37 Bi2 C25 93.88(12) . . ?
C37 Bi2 Cl2 91.91(9) . . ?
C25 Bi2 Cl2 89.62(9) . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 Bi1 118.0(2) . . ?
C6 C1 Bi1 120.8(2) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 123.2(3) . . ?
C5 C6 C7 118.6(3) . . ?
C8 C7 C12 118.4(3) . . ?
C8 C7 C6 120.7(3) . . ?
C12 C7 C6 120.8(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 119.7(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 119.4(3) . . ?
C14 C13 Bi1 124.0(2) . . ?
C18 C13 Bi1 116.2(2) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 119.7(3) . . ?
C17 C18 C19 119.8(3) . . ?
C13 C18 C19 120.5(3) . . ?
C24 C19 C20 118.8(3) . . ?
C24 C19 C18 120.6(3) . . ?
C20 C19 C18 120.6(3) . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 120.8(3) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C26 C25 C30 119.2(3) . . ?
C26 C25 Bi2 120.2(3) . . ?
C30 C25 Bi2 120.0(3) . . ?
C27 C26 C25 121.4(3) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 119.5(3) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.6(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C25 119.3(3) . . ?
C29 C30 C31 119.0(3) . . ?
C25 C30 C31 121.7(3) . . ?
C36 C31 C32 119.1(3) . . ?
C36 C31 C30 120.7(3) . . ?
C32 C31 C30 120.2(3) . . ?
C33 C32 C31 120.5(4) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 120.0(4) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 119.8(4) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.2(4) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 120.5(3) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C38 C37 C42 120.1(3) . . ?
C38 C37 Bi2 123.0(3) . . ?
C42 C37 Bi2 116.8(2) . . ?
C37 C38 C39 120.4(3) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C38 C39 C40 119.5(3) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C41 C40 C39 120.1(3) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C40 C41 C42 120.9(3) . . ?
C40 C41 H41 119.5 . . ?
C42 C41 H41 119.5 . . ?
C41 C42 C37 118.8(3) . . ?
C41 C42 C43 120.4(3) . . ?
C37 C42 C43 120.8(3) . . ?
C48 C43 C44 119.0(3) . . ?
C48 C43 C42 119.9(3) . . ?
C44 C43 C42 121.1(3) . . ?
C45 C44 C43 120.1(4) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C46 C45 C44 120.2(4) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C47 C46 C45 120.2(4) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C46 C47 C48 120.4(4) . . ?
C46 C47 H47 119.8 . . ?
C48 C47 H47 119.8 . . ?
C47 C48 C43 120.2(3) . . ?
C47 C48 H48 119.9 . . ?
C43 C48 H48 119.9 . . ?

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
C6 C1 C2 C3 -0.4(5) . . . . ?
Bi1 C1 C2 C3 169.3(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
Bi1 C1 C6 C5 -167.9(2) . . . . ?
C2 C1 C6 C7 -176.5(3) . . . . ?
Bi1 C1 C6 C7 14.1(4) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C4 C5 C6 C7 176.9(3) . . . . ?
C1 C6 C7 C8 -133.2(4) . . . . ?
C5 C6 C7 C8 48.9(5) . . . . ?
C1 C6 C7 C12 50.6(5) . . . . ?
C5 C6 C7 C12 -127.4(4) . . . . ?
C12 C7 C8 C9 -0.9(5) . . . . ?
C6 C7 C8 C9 -177.3(3) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
C9 C10 C11 C12 -1.2(6) . . . . ?
C10 C11 C12 C7 0.8(5) . . . . ?
C8 C7 C12 C11 0.3(5) . . . . ?
C6 C7 C12 C11 176.6(3) . . . . ?
C18 C13 C14 C15 -1.0(5) . . . . ?
Bi1 C13 C14 C15 172.6(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 1.4(6) . . . . ?
C15 C16 C17 C18 -0.5(6) . . . . ?
C16 C17 C18 C13 -1.2(5) . . . . ?
C16 C17 C18 C19 179.0(3) . . . . ?
C14 C13 C18 C17 1.9(5) . . . . ?
Bi1 C13 C18 C17 -172.2(2) . . . . ?
C14 C13 C18 C19 -178.3(3) . . . . ?
Bi1 C13 C18 C19 7.7(4) . . . . ?
C17 C18 C19 C24 -124.0(4) . . . . ?
C13 C18 C19 C24 56.2(4) . . . . ?
C17 C18 C19 C20 55.4(4) . . . . ?
C13 C18 C19 C20 -124.4(4) . . . . ?
C24 C19 C20 C21 0.2(5) . . . . ?
C18 C19 C20 C21 -179.1(3) . . . . ?
C19 C20 C21 C22 0.0(5) . . . . ?
C20 C21 C22 C23 0.2(5) . . . . ?
C21 C22 C23 C24 -0.5(5) . . . . ?
C22 C23 C24 C19 0.7(5) . . . . ?
C20 C19 C24 C23 -0.5(5) . . . . ?
C18 C19 C24 C23 178.8(3) . . . . ?
C30 C25 C26 C27 0.2(5) . . . . ?
Bi2 C25 C26 C27 -170.8(3) . . . . ?
C25 C26 C27 C28 1.3(5) . . . . ?
C26 C27 C28 C29 -1.5(6) . . . . ?
C27 C28 C29 C30 0.3(6) . . . . ?
C28 C29 C30 C25 1.1(5) . . . . ?
C28 C29 C30 C31 -177.3(3) . . . . ?
C26 C25 C30 C29 -1.4(5) . . . . ?
Bi2 C25 C30 C29 169.6(3) . . . . ?
C26 C25 C30 C31 177.0(3) . . . . ?
Bi2 C25 C30 C31 -12.0(4) . . . . ?
C29 C30 C31 C36 125.0(4) . . . . ?
C25 C30 C31 C36 -53.4(5) . . . . ?
C29 C30 C31 C32 -53.3(5) . . . . ?
C25 C30 C31 C32 128.3(4) . . . . ?
C36 C31 C32 C33 1.2(5) . . . . ?
C30 C31 C32 C33 179.5(3) . . . . ?
C31 C32 C33 C34 -1.1(6) . . . . ?
C32 C33 C34 C35 0.2(6) . . . . ?
C33 C34 C35 C36 0.5(6) . . . . ?
C34 C35 C36 C31 -0.4(5) . . . . ?
C32 C31 C36 C35 -0.4(5) . . . . ?
C30 C31 C36 C35 -178.7(3) . . . . ?
C42 C37 C38 C39 1.3(5) . . . . ?
Bi2 C37 C38 C39 -175.6(3) . . . . ?
C37 C38 C39 C40 2.0(5) . . . . ?
C38 C39 C40 C41 -2.7(6) . . . . ?
C39 C40 C41 C42 0.1(5) . . . . ?
C40 C41 C42 C37 3.2(5) . . . . ?
C40 C41 C42 C43 -174.4(3) . . . . ?
C38 C37 C42 C41 -3.9(5) . . . . ?
Bi2 C37 C42 C41 173.2(2) . . . . ?
C38 C37 C42 C43 173.7(3) . . . . ?
Bi2 C37 C42 C43 -9.3(4) . . . . ?
C41 C42 C43 C48 119.9(4) . . . . ?
C37 C42 C43 C48 -57.6(4) . . . . ?
C41 C42 C43 C44 -57.0(5) . . . . ?
C37 C42 C43 C44 125.5(4) . . . . ?
C48 C43 C44 C45 -0.3(5) . . . . ?
C42 C43 C44 C45 176.7(3) . . . . ?
C43 C44 C45 C46 0.2(5) . . . . ?
C44 C45 C46 C47 0.0(5) . . . . ?
C45 C46 C47 C48 -0.1(5) . . . . ?
C46 C47 C48 C43 -0.1(5) . . . . ?
C44 C43 C48 C47 0.3(5) . . . . ?
C42 C43 C48 C47 -176.7(3) . . . . ?

_refine_diff_density_max         1.026
_refine_diff_density_min         -1.224
_refine_diff_density_rms         0.114

_shelxl_version_number           2013-4

