# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_tdx049
_database_code_depnum_ccdc_archive 'CCDC 2151498'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 Bi N'
_chemical_formula_sum            'C14 H16 Bi N'
_chemical_formula_weight         407.26
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3621(4)
_cell_length_b                   9.7525(3)
_cell_length_c                   14.8523(6)
_cell_angle_alpha                80.019(3)
_cell_angle_beta                 78.242(3)
_cell_angle_gamma                88.274(3)
_cell_volume                     1307.51(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18869
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.179
_cell_measurement_theta_min      2.120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.458
_exptl_absorpt_correction_T_max  0.1075
_exptl_absorpt_correction_T_min  0.0355
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.83.8.0 (STOE, 2020)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.069
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_rad          0.0569
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15578
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.179
_diffrn_reflns_theta_min         2.120
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'STOE IPDS 2T'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5603
_reflns_number_total             7042
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.833
_refine_diff_density_min         -1.547
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         7042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+2.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0639
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.79590(2) 0.33654(2) 0.21662(2) 0.01677(5) Uani 1 1 d . . . . .
N1 N 0.5963(4) 0.4640(4) 0.2035(3) 0.0203(7) Uani 1 1 d . . . . .
C1 C 0.7522(4) 0.2891(4) 0.3733(3) 0.0185(8) Uani 1 1 d . . . . .
C2 C 0.9478(5) 0.5200(4) 0.1983(3) 0.0194(8) Uani 1 1 d . . . . .
C5 C 0.5674(5) 0.5756(4) 0.2585(4) 0.0258(10) Uani 1 1 d . . . . .
H5A H 0.550097 0.535731 0.325057 0.039 Uiso 1 1 calc GR . . . .
H5B H 0.481021 0.627376 0.244423 0.039 Uiso 1 1 calc GR . . . .
H5C H 0.651696 0.638680 0.242918 0.039 Uiso 1 1 calc GR . . . .
C6 C 0.6100(5) 0.5257(5) 0.1045(4) 0.0269(10) Uani 1 1 d . . . . .
H6A H 0.689958 0.593913 0.086348 0.040 Uiso 1 1 calc GR . . . .
H6B H 0.518685 0.572056 0.094876 0.040 Uiso 1 1 calc GR . . . .
H6C H 0.630687 0.452291 0.066260 0.040 Uiso 1 1 calc GR . . . .
C9 C 0.7463(4) 0.1484(4) 0.4132(3) 0.0186(8) Uani 1 1 d . . . . .
H9 H 0.758735 0.079649 0.374134 0.022 Uiso 1 1 calc R . . . .
C10 C 0.7225(5) 0.1079(4) 0.5095(3) 0.0209(8) Uani 1 1 d . . . . .
H10 H 0.719034 0.011786 0.535920 0.025 Uiso 1 1 calc R . . . .
C11 C 0.7037(5) 0.2076(4) 0.5670(3) 0.0214(9) Uani 1 1 d . . . . .
H11 H 0.686166 0.179892 0.632865 0.026 Uiso 1 1 calc R . . . .
C12 C 0.7106(5) 0.3480(4) 0.5281(3) 0.0190(8) Uani 1 1 d . . . . .
H12 H 0.699058 0.416311 0.567505 0.023 Uiso 1 1 calc R . . . .
C13 C 0.7342(4) 0.3889(4) 0.4320(3) 0.0182(8) Uani 1 1 d . . . . .
H13 H 0.738094 0.485097 0.405877 0.022 Uiso 1 1 calc R . . . .
C14 C 1.0082(5) 0.5597(4) 0.2688(3) 0.0211(8) Uani 1 1 d . . . . .
H14 H 0.977322 0.514737 0.331664 0.025 Uiso 1 1 calc R . . . .
C15 C 1.1127(5) 0.6642(5) 0.2476(4) 0.0256(9) Uani 1 1 d . . . . .
H15 H 1.150741 0.691981 0.296280 0.031 Uiso 1 1 calc R . . . .
C16 C 1.1623(5) 0.7286(5) 0.1565(4) 0.0270(10) Uani 1 1 d . . . . .
H16 H 1.237143 0.797136 0.142357 0.032 Uiso 1 1 calc R . . . .
C17 C 1.1018(6) 0.6923(5) 0.0856(4) 0.0291(10) Uani 1 1 d . . . . .
H17 H 1.132142 0.738372 0.022934 0.035 Uiso 1 1 calc R . . . .
C18 C 0.9971(5) 0.5885(5) 0.1076(4) 0.0255(9) Uani 1 1 d . . . . .
H18 H 0.957390 0.562918 0.058800 0.031 Uiso 1 1 calc R . . . .
Bi2 Bi 0.29692(2) 0.32525(2) 0.20922(2) 0.01928(5) Uani 1 1 d . . . . .
N2 N 0.1055(4) 0.1952(4) 0.2064(3) 0.0230(8) Uani 1 1 d . . . . .
C3 C 0.2571(5) 0.2830(4) 0.3655(3) 0.0201(9) Uani 1 1 d . . . . .
C4 C 0.4618(5) 0.1548(4) 0.1845(3) 0.0205(8) Uani 1 1 d . . . . .
C7 C 0.1121(5) 0.1859(5) 0.1084(4) 0.0292(10) Uani 1 1 d . . . . .
H7A H 0.122774 0.279467 0.070910 0.044 Uiso 1 1 calc GR . . . .
H7B H 0.022160 0.142848 0.102223 0.044 Uiso 1 1 calc GR . . . .
H7C H 0.195890 0.129030 0.086517 0.044 Uiso 1 1 calc GR . . . .
C8 C 0.1006(5) 0.0542(5) 0.2605(4) 0.0283(10) Uani 1 1 d . . . . .
H8A H 0.187220 0.002861 0.235882 0.042 Uiso 1 1 calc GR . . . .
H8B H 0.012710 0.006111 0.255633 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.098415 0.059278 0.326038 0.042 Uiso 1 1 calc GR . . . .
C19 C 0.1171(5) 0.2631(5) 0.4180(3) 0.0230(9) Uani 1 1 d . . . . .
H19 H 0.037332 0.264409 0.387240 0.028 Uiso 1 1 calc R . . . .
C20 C 0.0909(5) 0.2410(5) 0.5150(4) 0.0255(9) Uani 1 1 d . . . . .
H20 H -0.005902 0.225915 0.550072 0.031 Uiso 1 1 calc R . . . .
C21 C 0.2065(5) 0.2413(4) 0.5605(3) 0.0228(9) Uani 1 1 d . . . . .
H21 H 0.189289 0.227025 0.626784 0.027 Uiso 1 1 calc R . . . .
C22 C 0.3472(5) 0.2624(4) 0.5086(3) 0.0225(9) Uani 1 1 d . . . . .
H22 H 0.426643 0.262363 0.539432 0.027 Uiso 1 1 calc R . . . .
C23 C 0.3729(5) 0.2836(4) 0.4116(3) 0.0208(8) Uani 1 1 d . . . . .
H23 H 0.469688 0.298557 0.376519 0.025 Uiso 1 1 calc R . . . .
C24 C 0.5243(5) 0.1468(5) 0.0912(3) 0.0261(10) Uani 1 1 d . . . . .
H24 H 0.494493 0.209381 0.042044 0.031 Uiso 1 1 calc R . . . .
C25 C 0.6306(6) 0.0466(5) 0.0707(4) 0.0303(11) Uani 1 1 d . . . . .
H25 H 0.672679 0.041314 0.007539 0.036 Uiso 1 1 calc R . . . .
C26 C 0.6745(6) -0.0448(5) 0.1420(4) 0.0293(11) Uani 1 1 d . . . . .
H26 H 0.747894 -0.111632 0.127841 0.035 Uiso 1 1 calc R . . . .
C27 C 0.6115(5) -0.0388(5) 0.2339(4) 0.0275(10) Uani 1 1 d . . . . .
H27 H 0.640154 -0.102846 0.282813 0.033 Uiso 1 1 calc R . . . .
C28 C 0.5066(5) 0.0603(4) 0.2547(3) 0.0225(9) Uani 1 1 d . . . . .
H28 H 0.464410 0.063725 0.318056 0.027 Uiso 1 1 calc R . . . .


_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 N1 2.236(4) . ?
Bi1 C1 2.247(5) . ?
Bi1 C2 2.263(4) . ?
N1 C5 1.457(5) . ?
N1 C6 1.470(6) . ?
C1 C9 1.395(6) . ?
C1 C13 1.399(6) . ?
C2 C14 1.402(6) . ?
C2 C18 1.389(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.389(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.384(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(6) . ?
C18 H18 0.9500 . ?
Bi2 N2 2.238(4) . ?
Bi2 C3 2.241(5) . ?
Bi2 C4 2.260(4) . ?
N2 C7 1.462(6) . ?
N2 C8 1.464(6) . ?
C3 C19 1.382(6) . ?
C3 C23 1.396(6) . ?
C4 C24 1.404(6) . ?
C4 C28 1.391(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.392(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(7) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.399(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.384(6) . ?
C28 H28 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
N1 Bi1 C1 96.94(14) . . ?
N1 Bi1 C2 95.67(14) . . ?
C1 Bi1 C2 97.27(16) . . ?
C5 N1 Bi1 116.7(3) . . ?
C5 N1 C6 108.3(4) . . ?
C6 N1 Bi1 107.4(3) . . ?
C9 C1 Bi1 116.0(3) . . ?
C9 C1 C13 118.9(4) . . ?
C13 C1 Bi1 125.1(3) . . ?
C14 C2 Bi1 125.4(3) . . ?
C18 C2 Bi1 116.6(3) . . ?
C18 C2 C14 117.6(4) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C9 H9 119.7 . . ?
C10 C9 C1 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C1 C13 H13 119.8 . . ?
C12 C13 C1 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C2 C14 H14 119.8 . . ?
C15 C14 C2 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.0(5) . . ?
C18 C17 H17 120.5 . . ?
C2 C18 H18 118.8 . . ?
C17 C18 C2 122.4(5) . . ?
C17 C18 H18 118.8 . . ?
N2 Bi2 C3 92.53(15) . . ?
N2 Bi2 C4 94.52(15) . . ?
C3 Bi2 C4 97.12(16) . . ?
C7 N2 Bi2 106.3(3) . . ?
C7 N2 C8 108.8(4) . . ?
C8 N2 Bi2 115.5(3) . . ?
C19 C3 Bi2 120.8(3) . . ?
C19 C3 C23 118.8(4) . . ?
C23 C3 Bi2 120.4(3) . . ?
C24 C4 Bi2 116.9(3) . . ?
C28 C4 Bi2 124.7(3) . . ?
C28 C4 C24 118.4(4) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C19 H19 119.4 . . ?
C3 C19 C20 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.5(5) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.5(4) . . ?
C23 C22 H22 119.8 . . ?
C3 C23 H23 119.9 . . ?
C22 C23 C3 120.3(4) . . ?
C22 C23 H23 119.9 . . ?
C4 C24 H24 120.0 . . ?
C25 C24 C4 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.3(5) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.9(4) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.1(5) . . ?
C28 C27 H27 119.9 . . ?
C4 C28 H28 119.4 . . ?
C27 C28 C4 121.2(4) . . ?
C27 C28 H28 119.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx012
_database_code_depnum_ccdc_archive 'CCDC 2151508'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2020-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 As Bi'
_chemical_formula_sum            'C20 H28 As Bi'
_chemical_formula_weight         552.32
_chemical_melting_point          ?
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'
As As 0.0499 2.0058 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.3753(3)
_cell_length_b                   18.4967(9)
_cell_length_c                   17.0593(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.766(3)
_cell_angle_gamma                90
_cell_volume                     2001.49(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13516
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      3.256
_cell_measurement_theta_min      51.992
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.446
_exptl_absorpt_correction_T_max  0.5867
_exptl_absorpt_correction_T_min  0.2009
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.76.6.0 (STOE, 2019)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0293
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12090
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.628
_diffrn_ambient_temperature      100
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           0.000
_diffrn_source_power             0.000
_diffrn_source_voltage           0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3057
_reflns_number_total             3927
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.465
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0717
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C5(H5), C9(H9), C14(H14), C6(H6), C12(H12), C13(H13),
 C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C15(H15A,H15B,
 H15C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72922(3) 0.66809(2) 0.24822(2) 0.02348(8) Uani 1 1 d . . . . .
As1 As 0.42158(9) 0.70827(4) 0.33989(3) 0.02282(14) Uani 1 1 d . . . . .
C1 C 0.4943(9) 0.6209(4) 0.1544(3) 0.0244(13) Uani 1 1 d . . . . .
C18 C 0.8129(9) 0.7274(4) 0.4525(4) 0.0301(15) Uani 1 1 d . . . . .
H18A H 0.886611 0.692911 0.421381 0.045 Uiso 1 1 calc GR . . . .
H18B H 0.875465 0.726329 0.507394 0.045 Uiso 1 1 calc GR . . . .
H18C H 0.825918 0.776159 0.431091 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.4224(10) 0.5838(4) 0.0184(4) 0.0285(14) Uani 1 1 d . . . . .
H8 H 0.465258 0.579998 -0.033241 0.034 Uiso 1 1 calc R . . . .
C4 C 0.5794(9) 0.7067(4) 0.4490(3) 0.0259(13) Uani 1 1 d . . . . .
C2 C 0.7954(9) 0.5610(4) 0.3092(4) 0.0257(13) Uani 1 1 d . . . . .
C7 C 0.2287(10) 0.5589(4) 0.0334(4) 0.0281(14) Uani 1 1 d . . . . .
H7 H 0.138783 0.537135 -0.007739 0.034 Uiso 1 1 calc R . . . .
C5 C 0.2959(9) 0.5961(3) 0.1686(4) 0.0267(14) Uani 1 1 d . . . . .
H5 H 0.250593 0.600264 0.219742 0.032 Uiso 1 1 calc R . . . .
C9 C 0.5575(9) 0.6147(3) 0.0787(3) 0.0237(13) Uani 1 1 d . . . . .
H9 H 0.692671 0.631560 0.068212 0.028 Uiso 1 1 calc R . . . .
C14 C 0.9882(9) 0.5523(4) 0.3535(4) 0.0286(14) Uani 1 1 d . . . . .
H14 H 1.090681 0.589685 0.354350 0.034 Uiso 1 1 calc R . . . .
C6 C 0.1622(10) 0.5649(4) 0.1072(4) 0.0302(15) Uani 1 1 d . . . . .
H6 H 0.026309 0.548055 0.116773 0.036 Uiso 1 1 calc R . . . .
C16 C 0.3248(10) 0.8057(4) 0.2138(4) 0.0326(15) Uani 1 1 d . . . . .
H16A H 0.443753 0.786659 0.188014 0.049 Uiso 1 1 calc GR . . . .
H16B H 0.285962 0.853523 0.192194 0.049 Uiso 1 1 calc GR . . . .
H16C H 0.204255 0.772899 0.204471 0.049 Uiso 1 1 calc GR . . . .
C12 C 0.8864(10) 0.4355(4) 0.3959(4) 0.0316(15) Uani 1 1 d . . . . .
H12 H 0.916245 0.393009 0.426289 0.038 Uiso 1 1 calc R . . . .
C13 C 1.0332(10) 0.4894(4) 0.3969(4) 0.0312(15) Uani 1 1 d . . . . .
H13 H 1.165774 0.484043 0.427140 0.037 Uiso 1 1 calc R . . . .
C3 C 0.3881(9) 0.8122(3) 0.3026(4) 0.0279(14) Uani 1 1 d . . . . .
C20 C 0.4669(10) 0.7576(4) 0.5020(4) 0.0310(15) Uani 1 1 d . . . . .
H20A H 0.490046 0.807792 0.486798 0.047 Uiso 1 1 calc GR . . . .
H20B H 0.523247 0.750299 0.557052 0.047 Uiso 1 1 calc GR . . . .
H20C H 0.315463 0.747079 0.496154 0.047 Uiso 1 1 calc GR . . . .
C15 C 0.2050(10) 0.8454(4) 0.3398(4) 0.0369(17) Uani 1 1 d . . . . .
H15A H 0.082653 0.813214 0.332100 0.055 Uiso 1 1 calc GR . . . .
H15B H 0.169418 0.892267 0.315043 0.055 Uiso 1 1 calc GR . . . .
H15C H 0.244397 0.852390 0.396304 0.055 Uiso 1 1 calc GR . . . .
C19 C 0.5569(10) 0.6294(4) 0.4777(4) 0.0288(14) Uani 1 1 d . . . . .
H19A H 0.407217 0.617983 0.478969 0.043 Uiso 1 1 calc GR . . . .
H19B H 0.630076 0.624460 0.530747 0.043 Uiso 1 1 calc GR . . . .
H19C H 0.619001 0.596073 0.441810 0.043 Uiso 1 1 calc GR . . . .
C17 C 0.5843(9) 0.8601(4) 0.3160(4) 0.0303(15) Uani 1 1 d . . . . .
H17A H 0.621649 0.866763 0.372674 0.045 Uiso 1 1 calc GR . . . .
H17B H 0.555011 0.907296 0.291083 0.045 Uiso 1 1 calc GR . . . .
H17C H 0.701854 0.837028 0.292790 0.045 Uiso 1 1 calc GR . . . .
C10 C 0.6498(10) 0.5044(4) 0.3082(4) 0.0299(14) Uani 1 1 d . . . . .
H10 H 0.517566 0.508598 0.277488 0.036 Uiso 1 1 calc R . . . .
C11 C 0.6968(10) 0.4425(4) 0.3514(4) 0.0332(15) Uani 1 1 d . . . . .
H11 H 0.596667 0.404366 0.350246 0.040 Uiso 1 1 calc R . . . .


_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 As1 2.7315(7) . ?
Bi1 C1 2.255(6) . ?
Bi1 C2 2.257(6) . ?
As1 C4 2.025(6) . ?
As1 C3 2.029(6) . ?
C1 C5 1.390(8) . ?
C1 C9 1.395(8) . ?
C18 C4 1.532(8) . ?
C8 C7 1.366(9) . ?
C8 C9 1.397(8) . ?
C4 C20 1.532(8) . ?
C4 C19 1.523(9) . ?
C2 C14 1.386(8) . ?
C2 C10 1.399(9) . ?
C7 C6 1.372(9) . ?
C5 C6 1.406(8) . ?
C14 C13 1.393(9) . ?
C16 C3 1.532(9) . ?
C12 C13 1.367(10) . ?
C12 C11 1.368(9) . ?
C3 C15 1.514(9) . ?
C3 C17 1.532(9) . ?
C10 C11 1.378(9) . ?

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
C1 Bi1 As1 92.75(16) . . ?
C1 Bi1 C2 93.9(2) . . ?
C2 Bi1 As1 94.97(15) . . ?
C4 As1 Bi1 101.73(17) . . ?
C4 As1 C3 109.2(3) . . ?
C3 As1 Bi1 97.89(19) . . ?
C5 C1 Bi1 123.7(4) . . ?
C5 C1 C9 119.1(5) . . ?
C9 C1 Bi1 117.1(4) . . ?
C7 C8 C9 120.1(6) . . ?
C18 C4 As1 115.1(4) . . ?
C18 C4 C20 109.5(5) . . ?
C20 C4 As1 108.4(4) . . ?
C19 C4 As1 104.7(4) . . ?
C19 C4 C18 110.1(5) . . ?
C19 C4 C20 108.8(5) . . ?
C14 C2 Bi1 117.9(5) . . ?
C14 C2 C10 118.1(6) . . ?
C10 C2 Bi1 123.9(4) . . ?
C8 C7 C6 120.9(6) . . ?
C1 C5 C6 120.0(6) . . ?
C1 C9 C8 120.1(6) . . ?
C2 C14 C13 120.7(6) . . ?
C7 C6 C5 119.7(6) . . ?
C13 C12 C11 120.3(6) . . ?
C12 C13 C14 119.9(6) . . ?
C16 C3 As1 104.2(4) . . ?
C15 C3 As1 108.4(4) . . ?
C15 C3 C16 108.0(5) . . ?
C15 C3 C17 110.8(6) . . ?
C17 C3 As1 116.3(4) . . ?
C17 C3 C16 108.8(5) . . ?
C11 C10 C2 120.5(6) . . ?
C12 C11 C10 120.5(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx032
_database_code_depnum_ccdc_archive 'CCDC 2151500'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 Bi P Si'
_chemical_formula_sum            'C19 H28 Bi P Si'
_chemical_formula_weight         524.45
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2419(3)
_cell_length_b                   8.9902(4)
_cell_length_c                   19.3583(10)
_cell_angle_alpha                77.940(4)
_cell_angle_beta                 88.394(4)
_cell_angle_gamma                75.687(4)
_cell_volume                     1029.04(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    26972
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.999
_cell_measurement_theta_min      2.152
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.699
_exptl_absorpt_correction_T_max  0.1737
_exptl_absorpt_correction_T_min  0.0232
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.76.6.0 (STOE, 2019)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             508
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0853
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.180
_diffrn_reflns_theta_min         2.152
_diffrn_ambient_temperature      100
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           0.000
_diffrn_source_power             0.000
_diffrn_source_voltage           0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4756
_reflns_number_total             5568
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.292
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0435
_refine_ls_wR_factor_ref         0.0442
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Bi1B)=Sof(P1B)=1-FVAR(1)
 Sof(Bi1A)=Sof(P1A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C9(H9), C8(H8), C13(H13), C7(H7), C12(H12), C5(H5),
 C11(H11), C6(H6)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Bi1A Bi -0.00885(2) 0.36732(2) 0.22764(2) 0.01979(4) Uani 0.9861(5) 1 d . . P A
1
P1A P 0.26946(12) 0.46091(9) 0.29718(4) 0.01801(15) Uani 0.9861(5) 1 d . . P A
1
Si1 Si 0.36043(13) 0.24620(9) 0.38619(4) 0.02127(17) Uani 1 1 d . . . . .
C14 C -0.0608(5) 0.7392(4) 0.27515(17) 0.0280(7) Uani 1 1 d . . . . .
H14A H 0.033998 0.765599 0.237086 0.042 Uiso 1 1 calc GR . . . .
H14B H -0.135136 0.832493 0.291125 0.042 Uiso 1 1 calc GR . . . .
H14C H -0.168290 0.693266 0.258977 0.042 Uiso 1 1 calc GR . . . .
C3 C 0.0771(5) 0.6223(3) 0.33592(16) 0.0223(6) Uani 1 1 d . . . . .
C1 C 0.2714(5) 0.1953(3) 0.18940(15) 0.0218(6) Uani 1 1 d . . . . .
C2 C -0.0227(5) 0.5519(3) 0.12823(16) 0.0217(6) Uani 1 1 d . . . . .
C16 C -0.0788(6) 0.5674(4) 0.39143(18) 0.0361(8) Uani 1 1 d . . . . .
H16A H -0.163301 0.508575 0.372523 0.054 Uiso 1 1 calc GR . . . .
H16B H -0.177130 0.656845 0.404650 0.054 Uiso 1 1 calc GR . . . .
H16C H 0.005312 0.502113 0.432246 0.054 Uiso 1 1 calc GR . . . .
C18 C 0.1331(5) 0.1526(4) 0.4217(2) 0.0375(8) Uani 1 1 d . . . . .
H18A H 0.018864 0.227737 0.439059 0.056 Uiso 1 1 calc GR . . . .
H18B H 0.190559 0.064724 0.459466 0.056 Uiso 1 1 calc GR . . . .
H18C H 0.073161 0.117333 0.384698 0.056 Uiso 1 1 calc GR . . . .
C17 C 0.4866(5) 0.2989(4) 0.46145(17) 0.0285(7) Uani 1 1 d . . . . .
H17A H 0.606997 0.344612 0.444716 0.043 Uiso 1 1 calc GR . . . .
H17B H 0.540619 0.206100 0.497207 0.043 Uiso 1 1 calc GR . . . .
H17C H 0.376984 0.373050 0.481020 0.043 Uiso 1 1 calc GR . . . .
C19 C 0.5733(5) 0.0958(4) 0.35176(17) 0.0274(7) Uani 1 1 d . . . . .
H19A H 0.503688 0.051265 0.320312 0.041 Uiso 1 1 calc GR . . . .
H19B H 0.643933 0.014438 0.390503 0.041 Uiso 1 1 calc GR . . . .
H19C H 0.681767 0.144117 0.326724 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.1153(6) 0.7473(4) 0.04811(18) 0.0326(7) Uani 1 1 d . . . . .
H10 H 0.221584 0.804488 0.036866 0.039 Uiso 1 1 calc R . . . .
C4 C 0.4607(5) 0.2375(4) 0.16293(16) 0.0254(6) Uani 1 1 d . . . . .
H4 H 0.475605 0.338272 0.162110 0.030 Uiso 1 1 calc R . . . .
C9 C 0.1353(5) 0.6379(4) 0.11020(16) 0.0254(6) Uani 1 1 d . . . . .
H9 H 0.255744 0.620983 0.140571 0.030 Uiso 1 1 calc R . . . .
C8 C 0.2540(5) 0.0444(4) 0.19145(19) 0.0327(8) Uani 1 1 d . . . . .
H8 H 0.128368 0.014004 0.209741 0.039 Uiso 1 1 calc R . . . .
C13 C -0.1999(5) 0.5782(4) 0.08159(17) 0.0286(7) Uani 1 1 d . . . . .
H13 H -0.306714 0.521447 0.092521 0.034 Uiso 1 1 calc R . . . .
C7 C 0.4217(6) -0.0622(4) 0.1666(2) 0.0434(10) Uani 1 1 d . . . . .
H7 H 0.407705 -0.163497 0.168151 0.052 Uiso 1 1 calc R . . . .
C15 C 0.2292(6) 0.7041(4) 0.3665(2) 0.0378(8) Uani 1 1 d . . . . .
H15A H 0.322651 0.630070 0.403201 0.057 Uiso 1 1 calc GR . . . .
H15B H 0.141240 0.788982 0.385634 0.057 Uiso 1 1 calc GR . . . .
H15C H 0.319072 0.744325 0.329747 0.057 Uiso 1 1 calc GR . . . .
C12 C -0.2185(6) 0.6894(4) 0.01847(18) 0.0379(8) Uani 1 1 d . . . . .
H12 H -0.337342 0.706700 -0.012583 0.046 Uiso 1 1 calc R . . . .
C5 C 0.6289(5) 0.1313(4) 0.13755(18) 0.0332(8) Uani 1 1 d . . . . .
H5 H 0.754865 0.161211 0.119280 0.040 Uiso 1 1 calc R . . . .
C11 C -0.0614(6) 0.7731(4) 0.00231(18) 0.0370(8) Uani 1 1 d . . . . .
H11 H -0.074012 0.847471 -0.039690 0.044 Uiso 1 1 calc R . . . .
C6 C 0.6085(6) -0.0195(4) 0.1395(2) 0.0396(9) Uani 1 1 d . . . . .
H6 H 0.720625 -0.091265 0.122640 0.048 Uiso 1 1 calc R . . . .
Bi1B Bi 0.3692(12) 0.4639(9) 0.2030(4) 0.021(3) Uani 0.0139(5) 1 d . . P A 2
P1B P 0.085(9) 0.417(7) 0.302(3) 0.024(12) Uiso 0.0139(5) 1 d . . 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
Bi1A P1A 2.6201(7) . ?
Bi1A C1 2.251(3) . ?
Bi1A C2 2.251(3) . ?
P1A Si1 2.2672(11) . ?
P1A C3 1.911(3) . ?
Si1 C18 1.867(3) . ?
Si1 C17 1.872(3) . ?
Si1 C19 1.865(3) . ?
Si1 P1B 2.40(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C3 1.524(4) . ?
C3 C16 1.518(4) . ?
C3 C15 1.533(4) . ?
C3 P1B 2.07(6) . ?
C1 C4 1.382(4) . ?
C1 C8 1.380(4) . ?
C1 Bi1B 2.698(8) . ?
C2 C9 1.392(4) . ?
C2 C13 1.390(4) . ?
C2 Bi1B 2.733(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C9 1.372(4) . ?
C10 C11 1.378(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.384(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.395(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.373(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C11 1.369(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C11 H11 0.9300 . ?
C6 H6 0.9300 . ?
Bi1B P1B 2.62(6) . ?

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
C1 Bi1A P1A 90.92(7) . . ?
C1 Bi1A C2 93.05(10) . . ?
C2 Bi1A P1A 96.01(8) . . ?
Si1 P1A Bi1A 98.10(3) . . ?
C3 P1A Bi1A 102.10(9) . . ?
C3 P1A Si1 106.63(10) . . ?
C18 Si1 P1A 117.02(11) . . ?
C18 Si1 C17 107.94(16) . . ?
C18 Si1 P1B 85.1(13) . . ?
C17 Si1 P1A 108.94(11) . . ?
C17 Si1 P1B 126.8(13) . . ?
C19 Si1 P1A 106.89(11) . . ?
C19 Si1 C18 107.23(16) . . ?
C19 Si1 C17 108.56(14) . . ?
C19 Si1 P1B 116.3(13) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
C14 C3 P1A 107.7(2) . . ?
C14 C3 C15 108.6(3) . . ?
C14 C3 P1B 98.8(17) . . ?
C16 C3 P1A 115.5(2) . . ?
C16 C3 C14 108.4(3) . . ?
C16 C3 C15 110.8(3) . . ?
C16 C3 P1B 85.0(16) . . ?
C15 C3 P1A 105.6(2) . . ?
C15 C3 P1B 140.9(16) . . ?
C4 C1 Bi1A 121.6(2) . . ?
C4 C1 Bi1B 57.0(2) . . ?
C8 C1 Bi1A 119.6(2) . . ?
C8 C1 C4 118.8(3) . . ?
C8 C1 Bi1B 169.2(3) . . ?
C9 C2 Bi1A 124.5(2) . . ?
C9 C2 Bi1B 60.4(2) . . ?
C13 C2 Bi1A 117.0(2) . . ?
C13 C2 C9 118.5(3) . . ?
C13 C2 Bi1B 168.8(3) . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C1 C4 H4 119.6 . . ?
C1 C4 C5 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C2 C9 H9 119.6 . . ?
C10 C9 C2 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C1 C8 H8 119.7 . . ?
C1 C8 C7 120.7(3) . . ?
C7 C8 H8 119.7 . . ?
C2 C13 H13 119.8 . . ?
C2 C13 C12 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C8 C7 H7 119.8 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 120.1 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C1 Bi1B C2 74.0(2) . . ?
P1B Bi1B C1 75.7(12) . . ?
P1B Bi1B C2 77.8(13) . . ?
Si1 P1B Bi1B 94.2(18) . . ?
C3 P1B Si1 97(2) . . ?
C3 P1B Bi1B 94(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx021
_database_code_depnum_ccdc_archive 'CCDC 2151501'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 Bi N'
_chemical_formula_sum            'C20 H28 Bi N'
_chemical_formula_weight         491.41
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.075(3)
_cell_length_b                   8.710(3)
_cell_length_c                   26.474(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.97(4)
_cell_angle_gamma                90
_cell_volume                     1857.7(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22828
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.171
_cell_measurement_theta_min      1.542
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.488
_exptl_absorpt_correction_T_max  0.1718
_exptl_absorpt_correction_T_min  0.0640
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   '1.83.8.0 (STOE, 2020)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0669
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            22828
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.171
_diffrn_reflns_theta_min         1.542
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           0.000
_diffrn_source_power             0.000
_diffrn_source_voltage           0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3939
_reflns_number_total             4997
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.989
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4997
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0665
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C11(H11), C9(H9)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C17(H17A,
 H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.53578(2) 0.68294(2) 0.65227(2) 0.01969(5) Uani 1 1 d . . . . .
C6 C 0.9185(5) 0.4330(5) 0.56496(14) 0.0218(8) Uani 1 1 d . . . . .
H6 H 1.035628 0.435437 0.563338 0.026 Uiso 1 1 calc R . . . .
C5 C 0.8263(5) 0.3326(5) 0.53282(15) 0.0231(8) Uani 1 1 d . . . . .
C7 C 0.8475(5) 0.5284(5) 0.59884(14) 0.0211(8) Uani 1 1 d . . . . .
C13 C 0.3906(5) 0.4158(5) 0.57067(16) 0.0268(9) Uani 1 1 d . . . . .
H13A H 0.362957 0.374240 0.603438 0.040 Uiso 1 1 calc GR . . . .
H13B H 0.346520 0.347797 0.543482 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.341352 0.518132 0.565975 0.040 Uiso 1 1 calc GR . . . .
C3 C 0.5779(4) 0.4272(5) 0.56930(14) 0.0213(8) Uani 1 1 d . . . . .
C15 C 0.9569(5) 0.6296(5) 0.63288(16) 0.0239(8) Uani 1 1 d . . . . .
H15A H 0.961905 0.589003 0.667481 0.036 Uiso 1 1 calc GR . . . .
H15B H 0.911242 0.733864 0.632576 0.036 Uiso 1 1 calc GR . . . .
H15C H 1.068848 0.631894 0.620793 0.036 Uiso 1 1 calc GR . . . .
C1 C 0.6733(4) 0.5258(5) 0.60113(14) 0.0201(8) Uani 1 1 d . . . . .
C4 C 0.6543(5) 0.3319(5) 0.53608(15) 0.0233(8) Uani 1 1 d . . . . .
H4 H 0.588192 0.264259 0.514996 0.028 Uiso 1 1 calc R . . . .
C14 C 0.9076(6) 0.2276(5) 0.49701(17) 0.0311(10) Uani 1 1 d . . . . .
H14A H 0.993784 0.283984 0.480417 0.047 Uiso 1 1 calc GR . . . .
H14B H 0.824242 0.189694 0.471360 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.957958 0.140660 0.515876 0.047 Uiso 1 1 calc GR . . . .
C16 C 0.6736(6) 0.3566(5) 0.71032(16) 0.0272(9) Uani 1 1 d . . . . .
H16A H 0.661330 0.269311 0.733128 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.755664 0.331407 0.686003 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.566595 0.378773 0.692063 0.041 Uiso 1 1 calc GR . . . .
C12 C 0.7606(5) 0.7691(5) 0.75494(15) 0.0226(8) Uani 1 1 d . . . . .
C2 C 0.7035(5) 0.6467(5) 0.72414(15) 0.0207(8) Uani 1 1 d . . . . .
C8 C 0.7312(5) 0.4956(5) 0.74080(15) 0.0213(8) Uani 1 1 d . . . . .
N1 N 0.6359(4) 0.8965(4) 0.62139(13) 0.0239(7) Uani 1 1 d . . . . .
C11 C 0.8470(5) 0.7374(5) 0.80127(15) 0.0233(8) Uani 1 1 d . . . . .
H11 H 0.886297 0.820616 0.821987 0.028 Uiso 1 1 calc R . . . .
C18 C 0.7322(5) 0.9360(5) 0.74059(15) 0.0258(8) Uani 1 1 d . . . . .
H18A H 0.774826 0.955378 0.707404 0.039 Uiso 1 1 calc GR . . . .
H18B H 0.790479 1.001993 0.766011 0.039 Uiso 1 1 calc GR . . . .
H18C H 0.613120 0.958602 0.739081 0.039 Uiso 1 1 calc GR . . . .
C10 C 0.8771(5) 0.5896(5) 0.81794(15) 0.0233(8) Uani 1 1 d . . . . .
C19 C 0.5191(6) 1.0240(6) 0.62727(18) 0.0348(10) Uani 1 1 d . . . . .
H19A H 0.429638 1.018668 0.600374 0.052 Uiso 1 1 calc GR . . . .
H19B H 0.577959 1.121898 0.625035 0.052 Uiso 1 1 calc GR . . . .
H19C H 0.472098 1.016231 0.660317 0.052 Uiso 1 1 calc GR . . . .
C9 C 0.8195(5) 0.4694(5) 0.78722(15) 0.0233(8) Uani 1 1 d . . . . .
H9 H 0.840586 0.366748 0.798000 0.028 Uiso 1 1 calc R . . . .
C20 C 0.6673(6) 0.8876(5) 0.56718(16) 0.0299(9) Uani 1 1 d . . . . .
H20A H 0.733742 0.796085 0.561172 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.727630 0.979409 0.557486 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.561269 0.881329 0.546900 0.045 Uiso 1 1 calc GR . . . .
C17 C 0.9686(6) 0.5612(6) 0.86892(16) 0.0317(10) Uani 1 1 d . . . . .
H17A H 1.084659 0.535582 0.864097 0.048 Uiso 1 1 calc GR . . . .
H17B H 0.916312 0.475697 0.885868 0.048 Uiso 1 1 calc GR . . . .
H17C H 0.964191 0.653789 0.889794 0.048 Uiso 1 1 calc GR . . . .


_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 C1 2.269(4) . ?
Bi1 C2 2.280(4) . ?
Bi1 N1 2.208(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.398(6) . ?
C6 C7 1.377(5) . ?
C5 C4 1.397(6) . ?
C5 C14 1.501(6) . ?
C7 C15 1.503(5) . ?
C7 C1 1.412(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C3 1.519(5) . ?
C3 C1 1.397(5) . ?
C3 C4 1.385(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C4 H4 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C8 1.511(6) . ?
C12 C2 1.400(6) . ?
C12 C11 1.396(6) . ?
C12 C18 1.516(6) . ?
C2 C8 1.401(6) . ?
C8 C9 1.396(5) . ?
N1 C19 1.472(5) . ?
N1 C20 1.477(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.377(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C10 C9 1.387(6) . ?
C10 C17 1.513(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C9 H9 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C1 Bi1 C2 97.33(14) . . ?
N1 Bi1 C1 94.60(14) . . ?
N1 Bi1 C2 102.36(14) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C7 C6 C5 123.1(4) . . ?
C6 C5 C14 121.8(4) . . ?
C4 C5 C6 117.1(4) . . ?
C4 C5 C14 121.1(4) . . ?
C6 C7 C15 119.4(3) . . ?
C6 C7 C1 118.6(4) . . ?
C1 C7 C15 122.0(3) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
C1 C3 C13 122.3(4) . . ?
C4 C3 C13 117.7(4) . . ?
C4 C3 C1 120.0(3) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C1 Bi1 123.1(3) . . ?
C3 C1 Bi1 117.3(3) . . ?
C3 C1 C7 119.6(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
C2 C12 C18 123.1(4) . . ?
C11 C12 C2 119.1(4) . . ?
C11 C12 C18 117.8(4) . . ?
C12 C2 Bi1 122.2(3) . . ?
C12 C2 C8 119.5(4) . . ?
C8 C2 Bi1 117.7(3) . . ?
C2 C8 C16 123.3(4) . . ?
C9 C8 C16 117.3(4) . . ?
C9 C8 C2 119.5(4) . . ?
C19 N1 Bi1 110.0(3) . . ?
C19 N1 C20 107.3(3) . . ?
C20 N1 Bi1 114.0(3) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 C12 122.2(4) . . ?
C10 C11 H11 118.9 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C10 C9 118.3(4) . . ?
C11 C10 C17 120.2(4) . . ?
C9 C10 C17 121.5(4) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 H9 119.3 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx024
_database_code_depnum_ccdc_archive 'CCDC 2151499'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H32 Bi N'
_chemical_formula_sum            'C22 H32 Bi N'
_chemical_formula_weight         519.46
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5236(5)
_cell_length_b                   9.9232(5)
_cell_length_c                   13.0242(6)
_cell_angle_alpha                96.380(4)
_cell_angle_beta                 104.891(4)
_cell_angle_gamma                115.291(4)
_cell_volume                     1040.56(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16312
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.151
_cell_measurement_theta_min      1.972
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.475
_exptl_absorpt_correction_T_max  0.2473
_exptl_absorpt_correction_T_min  0.0727
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.83.8.0 (STOE, 2020)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             508
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0701
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16312
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         1.672
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           0.000
_diffrn_source_power             0.000
_diffrn_source_voltage           0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4916
_reflns_number_total             5617
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.291
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5617
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.96 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C5(H5), C12(H12)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C14(H14A,H14B,H14C), C21(H21A,H21B,
 H21C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C22(H22A,
 H22B,H22C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.54700(2) 0.63142(2) 0.69428(2) 0.02223(4) Uani 1 1 d . . . . .
N1 N 0.5613(4) 0.8534(3) 0.7576(2) 0.0258(6) Uani 1 1 d D . . . .
C9 C 0.7907(4) 0.6238(4) 0.5689(3) 0.0246(6) Uani 1 1 d . . . . .
C7 C 1.0323(4) 0.8108(4) 0.9779(3) 0.0247(6) Uani 1 1 d . . . . .
H7 H 1.140550 0.895217 1.001033 0.030 Uiso 1 1 calc R . . . .
C6 C 0.9954(4) 0.7031(4) 1.0405(3) 0.0267(7) Uani 1 1 d . . . . .
C1 C 0.7541(4) 0.6732(4) 0.8476(3) 0.0234(6) Uani 1 1 d . . . . .
C16 C 0.9684(4) 0.9198(4) 0.8193(3) 0.0271(7) Uani 1 1 d . . . . .
H16A H 1.061668 1.015288 0.869543 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.876238 0.939107 0.786131 0.041 Uiso 1 1 calc GR . . . .
H16C H 1.001801 0.883496 0.761363 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.8747(4) 0.6543(4) 0.4941(3) 0.0263(7) Uani 1 1 d . . . . .
H10 H 0.939484 0.605040 0.487716 0.032 Uiso 1 1 calc R . . . .
C8 C 0.9146(4) 0.7978(4) 0.8824(3) 0.0248(6) Uani 1 1 d . . . . .
C5 C 0.8352(4) 0.5827(4) 1.0057(3) 0.0266(7) Uani 1 1 d . . . . .
H5 H 0.806411 0.509990 1.048359 0.032 Uiso 1 1 calc R . . . .
C2 C 0.6951(4) 0.6970(4) 0.5794(3) 0.0234(6) Uani 1 1 d . . . . .
C12 C 0.7694(5) 0.8223(4) 0.4387(3) 0.0300(7) Uani 1 1 d . . . . .
H12 H 0.761128 0.889895 0.394053 0.036 Uiso 1 1 calc R . . . .
C3 C 0.4097(4) 0.8422(4) 0.7763(3) 0.0258(6) Uani 1 1 d . . . . .
C4 C 0.7158(4) 0.5658(4) 0.9101(3) 0.0249(6) Uani 1 1 d . . . . .
C17 C 0.8073(5) 0.5134(4) 0.6361(3) 0.0307(7) Uani 1 1 d . . . . .
H17A H 0.843927 0.449071 0.599787 0.046 Uiso 1 1 calc GR . . . .
H17B H 0.700302 0.447799 0.642609 0.046 Uiso 1 1 calc GR . . . .
H17C H 0.888571 0.571825 0.709380 0.046 Uiso 1 1 calc GR . . . .
C11 C 0.8673(4) 0.7542(4) 0.4285(3) 0.0274(7) Uani 1 1 d . . . . .
C14 C 0.5451(5) 0.4283(4) 0.8773(3) 0.0314(7) Uani 1 1 d . . . . .
H14A H 0.463785 0.464554 0.875748 0.047 Uiso 1 1 calc GR . . . .
H14B H 0.543698 0.365967 0.930746 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.517570 0.365716 0.804322 0.047 Uiso 1 1 calc GR . . . .
C13 C 0.6830(4) 0.7950(4) 0.5121(3) 0.0268(7) Uani 1 1 d . . . . .
C21 C 0.4481(5) 1.0063(4) 0.8283(3) 0.0335(8) Uani 1 1 d . . . . .
H21A H 0.532715 1.044355 0.901202 0.050 Uiso 1 1 calc GR . . . .
H21B H 0.347470 1.005052 0.835258 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.488421 1.074167 0.781657 0.050 Uiso 1 1 calc GR . . . .
C15 C 1.1248(5) 0.7179(4) 1.1417(3) 0.0305(7) Uani 1 1 d . . . . .
H15A H 1.208679 0.700318 1.120988 0.046 Uiso 1 1 calc GR . . . .
H15B H 1.073650 0.641368 1.180306 0.046 Uiso 1 1 calc GR . . . .
H15C H 1.176751 0.821505 1.190086 0.046 Uiso 1 1 calc GR . . . .
C19 C 0.5784(5) 0.8730(5) 0.5161(3) 0.0341(8) Uani 1 1 d . . . . .
H19A H 0.467533 0.796439 0.510497 0.051 Uiso 1 1 calc GR . . . .
H19B H 0.571023 0.921598 0.454829 0.051 Uiso 1 1 calc GR . . . .
H19C H 0.628742 0.951724 0.585687 0.051 Uiso 1 1 calc GR . . . .
C18 C 0.9591(5) 0.7842(5) 0.3480(3) 0.0372(8) Uani 1 1 d . . . . .
H18A H 1.040516 0.747004 0.364501 0.056 Uiso 1 1 calc GR . . . .
H18B H 1.015575 0.895075 0.353868 0.056 Uiso 1 1 calc GR . . . .
H18C H 0.880824 0.730022 0.273264 0.056 Uiso 1 1 calc GR . . . .
C22 C 0.3548(6) 0.7393(5) 0.8530(4) 0.0403(9) Uani 1 1 d . . . . .
H22A H 0.327103 0.633658 0.819596 0.060 Uiso 1 1 calc GR . . . .
H22B H 0.257579 0.740150 0.864765 0.060 Uiso 1 1 calc GR . . . .
H22C H 0.444576 0.778179 0.923574 0.060 Uiso 1 1 calc GR . . . .
C20 C 0.2707(5) 0.7810(4) 0.6667(3) 0.0344(8) Uani 1 1 d . . . . .
H20A H 0.304304 0.848558 0.618451 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.172029 0.778340 0.678483 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.246056 0.676769 0.632529 0.052 Uiso 1 1 calc GR . . . .
H1 H 0.644(5) 0.883(5) 0.827(2) 0.054(14) Uiso 1 1 d 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
Bi1 N1 2.198(3) . ?
Bi1 C1 2.268(3) . ?
Bi1 C2 2.273(3) . ?
N1 C3 1.485(4) . ?
C9 C10 1.392(5) . ?
C9 C2 1.408(5) . ?
C9 C17 1.510(5) . ?
C7 C6 1.396(5) . ?
C7 C8 1.394(5) . ?
C6 C5 1.388(5) . ?
C6 C15 1.499(5) . ?
C1 C8 1.405(5) . ?
C1 C4 1.395(4) . ?
C16 C8 1.521(5) . ?
C10 C11 1.391(5) . ?
C5 C4 1.391(5) . ?
C2 C13 1.400(4) . ?
C12 C11 1.388(5) . ?
C12 C13 1.391(5) . ?
C3 C21 1.538(5) . ?
C3 C22 1.534(5) . ?
C3 C20 1.520(5) . ?
C4 C14 1.518(5) . ?
C11 C18 1.506(5) . ?
C13 C19 1.507(5) . ?

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
N1 Bi1 C1 90.74(11) . . ?
N1 Bi1 C2 100.55(11) . . ?
C1 Bi1 C2 98.66(12) . . ?
C3 N1 Bi1 114.9(2) . . ?
C10 C9 C2 119.1(3) . . ?
C10 C9 C17 118.1(3) . . ?
C2 C9 C17 122.7(3) . . ?
C8 C7 C6 121.8(3) . . ?
C7 C6 C15 120.9(3) . . ?
C5 C6 C7 117.7(3) . . ?
C5 C6 C15 121.4(3) . . ?
C8 C1 Bi1 124.7(2) . . ?
C4 C1 Bi1 116.3(2) . . ?
C4 C1 C8 119.1(3) . . ?
C11 C10 C9 122.5(3) . . ?
C7 C8 C1 119.5(3) . . ?
C7 C8 C16 117.6(3) . . ?
C1 C8 C16 122.9(3) . . ?
C6 C5 C4 121.8(3) . . ?
C9 C2 Bi1 117.7(2) . . ?
C13 C2 Bi1 122.9(2) . . ?
C13 C2 C9 119.1(3) . . ?
C11 C12 C13 122.2(3) . . ?
N1 C3 C21 107.1(3) . . ?
N1 C3 C22 113.3(3) . . ?
N1 C3 C20 109.3(3) . . ?
C22 C3 C21 108.8(3) . . ?
C20 C3 C21 108.8(3) . . ?
C20 C3 C22 109.4(3) . . ?
C1 C4 C14 121.9(3) . . ?
C5 C4 C1 120.2(3) . . ?
C5 C4 C14 117.9(3) . . ?
C10 C11 C18 121.2(3) . . ?
C12 C11 C10 117.2(3) . . ?
C12 C11 C18 121.5(3) . . ?
C2 C13 C19 122.0(3) . . ?
C12 C13 C2 119.7(3) . . ?
C12 C13 C19 118.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx040
_database_code_depnum_ccdc_archive 'CCDC 2151504'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 As Bi Si'
_chemical_formula_sum            'C19 H28 As Bi Si'
_chemical_formula_weight         568.40
_chemical_melting_point          ?
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'
As As 0.0499 2.0058 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   40.1899(18)
_cell_length_b                   6.1680(2)
_cell_length_c                   17.2741(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.327(3)
_cell_angle_gamma                90
_cell_volume                     4166.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19382
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.229
_cell_measurement_theta_min      2.407
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.092
_exptl_absorpt_correction_T_max  0.0590
_exptl_absorpt_correction_T_min  0.0313
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.83.8.0 (STOE, 2020)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0972
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19382
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.229
_diffrn_reflns_theta_min         2.407
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           0.000
_diffrn_source_power             0.000
_diffrn_source_voltage           0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4684
_reflns_number_total             5619
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.946
_refine_diff_density_min         -2.143
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         5619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+22.3475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0796
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C5(H5), C8(H8), C7(H7), C12(H12), C10(H10), C4(H4), C6(H6),
 C11(H11)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.60979(2) 0.50099(2) 0.54094(2) 0.01658(6) Uani 1 1 d . . . . .
As1 As 0.65332(2) 0.81554(6) 0.61443(2) 0.01869(9) Uani 1 1 d . . . . .
Si1 Si 0.67383(3) 0.65651(19) 0.74160(7) 0.0213(2) Uani 1 1 d . . . . .
C9 C 0.57786(11) 0.9398(7) 0.4542(2) 0.0225(8) Uani 1 1 d . . . . .
H9 H 0.601151 0.982871 0.463886 0.027 Uiso 1 1 calc R . . . .
C2 C 0.56940(10) 0.7386(6) 0.4804(2) 0.0186(7) Uani 1 1 d . . . . .
C13 C 0.53496(10) 0.6782(7) 0.4660(2) 0.0212(8) Uani 1 1 d . . . . .
H13 H 0.528937 0.540260 0.483078 0.025 Uiso 1 1 calc R . . . .
C5 C 0.56953(11) 0.1945(7) 0.7365(2) 0.0242(8) Uani 1 1 d . . . . .
H5 H 0.572011 0.056048 0.761229 0.029 Uiso 1 1 calc R . . . .
C1 C 0.58289(10) 0.4402(7) 0.6390(2) 0.0175(7) Uani 1 1 d . . . . .
C8 C 0.56255(10) 0.5985(6) 0.6640(2) 0.0190(7) Uani 1 1 d . . . . .
H8 H 0.559992 0.737029 0.639288 0.023 Uiso 1 1 calc R . . . .
C7 C 0.54621(11) 0.5534(7) 0.7245(3) 0.0243(8) Uani 1 1 d . . . . .
H7 H 0.532501 0.661427 0.741112 0.029 Uiso 1 1 calc R . . . .
C12 C 0.50956(10) 0.8177(8) 0.4269(2) 0.0258(9) Uani 1 1 d . . . . .
H12 H 0.486215 0.776505 0.418151 0.031 Uiso 1 1 calc R . . . .
C10 C 0.55220(12) 1.0796(7) 0.4135(2) 0.0258(9) Uani 1 1 d . . . . .
H10 H 0.558089 1.216050 0.394937 0.031 Uiso 1 1 calc R . . . .
C4 C 0.58594(11) 0.2380(7) 0.6756(3) 0.0232(8) Uani 1 1 d . . . . .
H4 H 0.599374 0.128548 0.658895 0.028 Uiso 1 1 calc R . . . .
C6 C 0.54974(11) 0.3499(7) 0.7613(2) 0.0262(9) Uani 1 1 d . . . . .
H6 H 0.538590 0.319433 0.802932 0.031 Uiso 1 1 calc R . . . .
C19 C 0.64241(13) 0.7308(8) 0.8009(3) 0.0322(10) Uani 1 1 d . . . . .
H19A H 0.638394 0.887621 0.797418 0.048 Uiso 1 1 calc GR . . . .
H19B H 0.651411 0.689744 0.856573 0.048 Uiso 1 1 calc GR . . . .
H19C H 0.620840 0.654347 0.779904 0.048 Uiso 1 1 calc GR . . . .
C11 C 0.51832(13) 1.0179(7) 0.4006(3) 0.0285(10) Uani 1 1 d . . . . .
H11 H 0.500903 1.113014 0.373452 0.034 Uiso 1 1 calc R . . . .
C3 C 0.69105(9) 0.7617(6) 0.5539(2) 0.0184(7) Uani 1 1 d . . . . .
C16 C 0.67591(13) 0.8291(9) 0.4680(3) 0.0361(11) Uani 1 1 d . . . . .
H16A H 0.658338 0.724453 0.443081 0.054 Uiso 1 1 calc GR . . . .
H16B H 0.694025 0.832743 0.438554 0.054 Uiso 1 1 calc GR . . . .
H16C H 0.665626 0.973397 0.467219 0.054 Uiso 1 1 calc GR . . . .
C17 C 0.67962(13) 0.3560(7) 0.7439(3) 0.0309(10) Uani 1 1 d . . . . .
H17A H 0.657854 0.286091 0.719374 0.046 Uiso 1 1 calc GR . . . .
H17B H 0.687194 0.307533 0.799234 0.046 Uiso 1 1 calc GR . . . .
H17C H 0.696851 0.316806 0.714447 0.046 Uiso 1 1 calc GR . . . .
C18 C 0.71596(12) 0.7806(8) 0.7917(3) 0.0321(10) Uani 1 1 d . . . . .
H18A H 0.733976 0.723220 0.767650 0.048 Uiso 1 1 calc GR . . . .
H18B H 0.721220 0.745005 0.848491 0.048 Uiso 1 1 calc GR . . . .
H18C H 0.714676 0.938418 0.785033 0.048 Uiso 1 1 calc GR . . . .
C14 C 0.70391(14) 0.5303(8) 0.5586(4) 0.0359(11) Uani 1 1 d . . . . .
H14A H 0.713832 0.492578 0.614233 0.054 Uiso 1 1 calc GR . . . .
H14B H 0.721390 0.516153 0.527627 0.054 Uiso 1 1 calc GR . . . .
H14C H 0.684832 0.432353 0.536957 0.054 Uiso 1 1 calc GR . . . .
C15 C 0.72076(13) 0.9167(9) 0.5904(3) 0.0363(11) Uani 1 1 d . . . . .
H15A H 0.712303 1.066215 0.587062 0.054 Uiso 1 1 calc GR . . . .
H15B H 0.738805 0.903936 0.560962 0.054 Uiso 1 1 calc GR . . . .
H15C H 0.729993 0.878134 0.646236 0.054 Uiso 1 1 calc GR . . . .


_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 As1 2.7227(4) . ?
Bi1 C2 2.257(4) . ?
Bi1 C1 2.241(4) . ?
As1 Si1 2.3733(12) . ?
As1 C3 2.058(4) . ?
Si1 C19 1.857(5) . ?
Si1 C17 1.867(5) . ?
Si1 C18 1.878(5) . ?
C9 H9 0.9500 . ?
C9 C2 1.390(6) . ?
C9 C10 1.402(6) . ?
C2 C13 1.399(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.386(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(6) . ?
C5 C6 1.375(6) . ?
C1 C8 1.404(6) . ?
C1 C4 1.391(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.385(6) . ?
C7 H7 0.9500 . ?
C7 C6 1.399(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.389(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(7) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C11 H11 0.9500 . ?
C3 C16 1.525(6) . ?
C3 C14 1.514(6) . ?
C3 C15 1.546(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 Bi1 As1 93.99(10) . . ?
C1 Bi1 As1 97.87(10) . . ?
C1 Bi1 C2 92.18(14) . . ?
Si1 As1 Bi1 100.71(3) . . ?
C3 As1 Bi1 96.76(11) . . ?
C3 As1 Si1 105.34(11) . . ?
C19 Si1 As1 105.84(15) . . ?
C19 Si1 C17 109.3(2) . . ?
C19 Si1 C18 107.5(2) . . ?
C17 Si1 As1 116.44(15) . . ?
C17 Si1 C18 107.5(2) . . ?
C18 Si1 As1 109.99(16) . . ?
C2 C9 H9 119.8 . . ?
C2 C9 C10 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C2 Bi1 121.8(3) . . ?
C9 C2 C13 119.1(4) . . ?
C13 C2 Bi1 119.1(3) . . ?
C2 C13 H13 119.7 . . ?
C12 C13 C2 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.7(4) . . ?
C8 C1 Bi1 122.2(3) . . ?
C4 C1 Bi1 119.1(3) . . ?
C4 C1 C8 118.7(4) . . ?
C1 C8 H8 119.9 . . ?
C7 C8 C1 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C8 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C6 C7 H7 119.8 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.2 . . ?
C5 C4 C1 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C1 C4 H4 119.7 . . ?
C5 C6 C7 119.3(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C16 C3 As1 105.9(3) . . ?
C16 C3 C15 109.0(4) . . ?
C14 C3 As1 114.0(3) . . ?
C14 C3 C16 111.3(4) . . ?
C14 C3 C15 109.8(4) . . ?
C15 C3 As1 106.5(3) . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx005
_database_code_depnum_ccdc_archive 'CCDC 2151505'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2020-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 Bi P'
_chemical_formula_sum            'C20 H28 Bi P'
_chemical_formula_weight         508.37
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.3994(3)
_cell_length_b                   18.2817(10)
_cell_length_c                   16.9616(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.753(4)
_cell_angle_gamma                90
_cell_volume                     1974.38(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    51580
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.49
_cell_measurement_theta_min      1.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.007
_exptl_absorpt_correction_T_max  0.1993
_exptl_absorpt_correction_T_min  0.0468
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'STOE LANA, 1.76.6'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0705
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24622
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_min         2.228
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'STOE IPDS 2T'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4462
_reflns_number_total             5012
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+5.9501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0504
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C9(H9), C5(H5), C14(H14), C7(H7), C10(H10), C8(H8),
 C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27799(2) 0.33059(2) 0.74740(2) 0.01848(4) Uani 1 1 d . . . . .
P1 P 0.57556(12) 0.29047(5) 0.65828(5) 0.01856(15) Uani 1 1 d . . . . .
C4 C 0.4360(5) 0.29249(18) 0.55390(18) 0.0207(6) Uani 1 1 d . . . . .
C13 C -0.0386(5) 0.5111(2) 0.6026(2) 0.0263(7) Uani 1 1 d . . . . .
H13 H -0.1714 0.5159 0.5726 0.032 Uiso 1 1 calc R . . . .
C3 C 0.6139(5) 0.19249(18) 0.69474(19) 0.0207(6) Uani 1 1 d . . . . .
C6 C 0.8402(5) 0.43539(19) 0.8893(2) 0.0252(7) Uani 1 1 d . . . . .
H6 H 0.9751 0.4527 0.8795 0.030 Uiso 1 1 calc R . . . .
C15 C 0.2025(5) 0.2720(2) 0.5458(2) 0.0251(7) Uani 1 1 d . . . . .
H15A H 0.1848 0.2241 0.5704 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.1500 0.2697 0.4896 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.1235 0.3089 0.5723 0.038 Uiso 1 1 calc GR . . . .
C16 C 0.5517(5) 0.2427(2) 0.49977(19) 0.0270(7) Uani 1 1 d . . . . .
H16A H 0.7031 0.2519 0.5088 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.5028 0.2530 0.4443 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.5231 0.1914 0.5116 0.041 Uiso 1 1 calc GR . . . .
C1 C 0.5097(5) 0.37861(18) 0.84220(18) 0.0210(6) Uani 1 1 d . . . . .
C9 C 0.4460(5) 0.38509(18) 0.91809(19) 0.0222(6) Uani 1 1 d . . . . .
H9 H 0.3109 0.3682 0.9282 0.027 Uiso 1 1 calc R . . . .
C2 C 0.2068(5) 0.43951(18) 0.68803(18) 0.0211(6) Uani 1 1 d . . . . .
C20 C 0.4271(5) 0.14093(19) 0.6802(2) 0.0252(6) Uani 1 1 d . . . . .
H20A H 0.3069 0.1613 0.7042 0.038 Uiso 1 1 calc GR . . . .
H20B H 0.4637 0.0932 0.7039 0.038 Uiso 1 1 calc GR . . . .
H20C H 0.3904 0.1351 0.6230 0.038 Uiso 1 1 calc GR . . . .
C19 C 0.6760(5) 0.1990(2) 0.7844(2) 0.0269(7) Uani 1 1 d . . . . .
H19A H 0.7870 0.2358 0.7943 0.040 Uiso 1 1 calc GR . . . .
H19B H 0.7274 0.1516 0.8053 0.040 Uiso 1 1 calc GR . . . .
H19C H 0.5532 0.2138 0.8107 0.040 Uiso 1 1 calc GR . . . .
C5 C 0.7082(5) 0.4041(2) 0.82830(19) 0.0238(6) Uani 1 1 d . . . . .
H5 H 0.7536 0.4001 0.7768 0.029 Uiso 1 1 calc R . . . .
C14 C 0.0114(5) 0.44702(19) 0.64396(19) 0.0233(6) Uani 1 1 d . . . . .
H14 H -0.0873 0.4081 0.6423 0.028 Uiso 1 1 calc R . . . .
C7 C 0.7744(6) 0.4413(2) 0.9648(2) 0.0273(7) Uani 1 1 d . . . . .
H7 H 0.8641 0.4628 1.0065 0.033 Uiso 1 1 calc R . . . .
C10 C 0.3471(5) 0.4974(2) 0.6916(2) 0.0260(7) Uani 1 1 d . . . . .
H10 H 0.4786 0.4932 0.7226 0.031 Uiso 1 1 calc R . . . .
C18 C 0.8039(5) 0.1600(2) 0.6585(2) 0.0298(7) Uani 1 1 d . . . . .
H18A H 0.7690 0.1532 0.6014 0.045 Uiso 1 1 calc GR . . . .
H18B H 0.8404 0.1127 0.6833 0.045 Uiso 1 1 calc GR . . . .
H18C H 0.9236 0.1934 0.6677 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.5778(5) 0.41594(18) 0.9789(2) 0.0254(7) Uani 1 1 d . . . . .
H8 H 0.5330 0.4197 1.0305 0.030 Uiso 1 1 calc R . . . .
C17 C 0.4593(5) 0.37161(19) 0.52599(19) 0.0254(7) Uani 1 1 d . . . . .
H17A H 0.3895 0.4047 0.5605 0.038 Uiso 1 1 calc GR . . . .
H17B H 0.3946 0.3765 0.4714 0.038 Uiso 1 1 calc GR . . . .
H17C H 0.6086 0.3842 0.5282 0.038 Uiso 1 1 calc GR . . . .
C11 C 0.2964(6) 0.5616(2) 0.6499(2) 0.0282(7) Uani 1 1 d . . . . .
H11 H 0.3935 0.6011 0.6523 0.034 Uiso 1 1 calc R . . . .
C12 C 0.1041(6) 0.5680(2) 0.6049(2) 0.0290(7) Uani 1 1 d . . . . .
H12 H 0.0705 0.6115 0.5757 0.035 Uiso 1 1 calc R . . . .


_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 P1 2.6508(8) . ?
Bi1 C1 2.253(3) . ?
Bi1 C2 2.257(3) . ?
P1 C4 1.902(3) . ?
P1 C3 1.903(3) . ?
C4 C15 1.533(4) . ?
C4 C16 1.535(4) . ?
C4 C17 1.534(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(5) . ?
C13 C12 1.383(5) . ?
C3 C20 1.523(4) . ?
C3 C19 1.537(5) . ?
C3 C18 1.536(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.391(5) . ?
C6 C7 1.391(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C1 C9 1.394(4) . ?
C1 C5 1.395(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.385(5) . ?
C2 C14 1.398(4) . ?
C2 C10 1.385(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5 H5 0.9500 . ?
C14 H14 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.384(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C8 H8 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.386(5) . ?
C12 H12 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
C1 Bi1 P1 93.20(8) . . ?
C1 Bi1 C2 93.65(12) . . ?
C2 Bi1 P1 96.55(8) . . ?
C4 P1 Bi1 103.19(10) . . ?
C4 P1 C3 110.74(15) . . ?
C3 P1 Bi1 98.73(10) . . ?
C15 C4 P1 116.2(2) . . ?
C15 C4 C16 109.0(3) . . ?
C15 C4 C17 109.1(3) . . ?
C16 C4 P1 109.6(2) . . ?
C17 C4 P1 104.7(2) . . ?
C17 C4 C16 107.9(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C20 C3 P1 117.1(2) . . ?
C20 C3 C19 109.2(3) . . ?
C20 C3 C18 109.6(3) . . ?
C19 C3 P1 105.1(2) . . ?
C18 C3 P1 108.4(2) . . ?
C18 C3 C19 106.8(3) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C1 Bi1 117.4(2) . . ?
C9 C1 C5 118.9(3) . . ?
C5 C1 Bi1 123.7(2) . . ?
C1 C9 H9 119.7 . . ?
C8 C9 C1 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C14 C2 Bi1 117.1(2) . . ?
C10 C2 Bi1 123.6(2) . . ?
C10 C2 C14 119.3(3) . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C5 C1 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C5 H5 119.8 . . ?
C13 C14 C2 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C2 C14 H14 119.9 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C2 C10 H10 119.8 . . ?
C2 C10 C11 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.8 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx026
_database_code_depnum_ccdc_archive 'CCDC 2151503'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H40 Bi P Si'
_chemical_formula_sum            'C25 H40 Bi P Si'
_chemical_formula_weight         608.61
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.1342(10)
_cell_length_b                   8.4111(10)
_cell_length_c                   31.257(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.857(8)
_cell_angle_gamma                90
_cell_volume                     2632.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    32598
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.687
_cell_measurement_theta_min      2.034
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.812
_exptl_absorpt_correction_T_max  0.0377
_exptl_absorpt_correction_T_min  0.0178
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   '1.83.8.0 (STOE, 2020)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.1573
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            31860
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.687
_diffrn_reflns_theta_min         2.034
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'STOE IPDS 2T'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4625
_reflns_number_total             5563
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.993
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0195
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Si1B-C20B \\sim Si1B-C22B \\sim Si1B-C21B
 with sigma of 0.02
 C24A-Si1B \\sim C20B-Si1B
 with sigma of 0.02
 C23A-Si1B \\sim C22B-Si1B
 with sigma of 0.02
 C25A-Si1B \\sim C21B-Si1B
 with sigma of 0.02
 C3A-C24A \\sim C3A-C20B
 with sigma of 0.02
 C3A-C23A \\sim C3A-C22B
 with sigma of 0.02
 C3A-C25A \\sim C3A-C21B
 with sigma of 0.02
 C24A-C3A \\sim C23A-C3A \\sim C25A-C3A
 with sigma of 0.02
 P1B-Si1B \\sim P1A-Si1A
 with sigma of 0.02
 Si1A-C20A \\sim Si1A-C21A \\sim Si1A-C22A
 with sigma of 0.02
 Si1A-C20A \\sim Si1A-C25B
 with sigma of 0.02
 Si1A-C22A \\sim Si1A-C23B
 with sigma of 0.02
 Si1A-C21A \\sim Si1A-C24B
 with sigma of 0.02
 C20A-C3B \\sim C25B-C3B
 with sigma of 0.02
 C22A-C3B \\sim C23B-C3B
 with sigma of 0.02
 C21A-C3B \\sim C24B-C3B
 with sigma of 0.02
 C25B-C3B \\sim C24B-C3B \\sim C23B-C3B
 with sigma of 0.02
 P1A-C3A \\sim P1B-C3B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C24A) = Uanis(C20B)
Uanis(C24B) = Uanis(C21A)
Uanis(C25B) = Uanis(C20A)
Uanis(C22A) = Uanis(C23B)
Uanis(Si1A) = Uanis(C3B)
4. Others
 Sof(P1B)=Sof(Si1B)=Sof(C3B)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C22B)=
 Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C21B)=Sof(H21D)=Sof(H21E)=Sof(H21F)=
 Sof(C25B)=Sof(H25D)=Sof(H25E)=Sof(H25F)=Sof(C24B)=Sof(H24D)=Sof(H24E)=
 Sof(H24F)=Sof(C23B)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(Si1A)=Sof(C3A)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C23A)=
 Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C22A)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(P1A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C12(H12), C5(H5)
5.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C24A(H24A,H24B,H24C), C23A(H23A,
 H23B,H23C), C20A(H20A,H20B,H20C), C25A(H25A,H25B,H25C), C19(H19A,H19B,H19C),
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C22A(H22A,H22B,
 H22C), C21A(H21A,H21B,H21C), C20B(H20D,H20E,H20F), C22B(H22D,H22E,H22F),
 C21B(H21D,H21E,H21F), C25B(H25D,H25E,H25F), C24B(H24D,H24E,H24F), C23B(H23D,
 H23E,H23F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.38791(2) 0.62502(2) 0.63951(2) 0.02389(4) Uani 1 1 d . . . . .
Si1A Si 0.0435(3) 0.5653(3) 0.59207(8) 0.0246(3) Uani 0.733(4) 1 d D . P A 1
C3A C 0.2112(14) 0.238(2) 0.6360(5) 0.018(2) Uani 0.733(4) 1 d D . P A 1
C2 C 0.5160(3) 0.7314(3) 0.59194(9) 0.0240(6) Uani 1 1 d . . . . .
C9 C 0.4905(3) 0.7219(3) 0.54648(9) 0.0263(6) Uani 1 1 d . . . . .
C14 C 0.5929(3) 0.3428(3) 0.59767(9) 0.0287(6) Uani 1 1 d . . . . .
H14A H 0.624664 0.437417 0.584062 0.043 Uiso 1 1 calc GR . . . .
H14B H 0.496094 0.332674 0.589065 0.043 Uiso 1 1 calc GR . . . .
H14C H 0.637234 0.248225 0.588330 0.043 Uiso 1 1 calc GR . . . .
C13 C 0.6250(3) 0.8216(3) 0.61195(9) 0.0261(6) Uani 1 1 d . . . . .
C10 C 0.5736(3) 0.8032(3) 0.52237(9) 0.0280(6) Uani 1 1 d . . . . .
H10 H 0.555040 0.796742 0.491689 0.034 Uiso 1 1 calc R . . . .
C4 C 0.6247(3) 0.3583(3) 0.64635(9) 0.0260(6) Uani 1 1 d . . . . .
C17 C 0.3783(3) 0.6253(3) 0.52239(9) 0.0302(6) Uani 1 1 d . . . . .
H17A H 0.398964 0.511907 0.526285 0.045 Uiso 1 1 calc GR . . . .
H17B H 0.367298 0.651787 0.491514 0.045 Uiso 1 1 calc GR . . . .
H17C H 0.295468 0.649194 0.533660 0.045 Uiso 1 1 calc GR . . . .
C24A C 0.3161(6) 0.1112(9) 0.6305(3) 0.0267(12) Uani 0.733(4) 1 d D . P A 1
H24A H 0.303256 0.018587 0.648468 0.040 Uiso 0.733(4) 1 calc GR . P A 1
H24B H 0.405651 0.155032 0.639536 0.040 Uiso 0.733(4) 1 calc GR . P A 1
H24C H 0.306426 0.078861 0.600075 0.040 Uiso 0.733(4) 1 calc GR . P A 1
C23A C 0.0690(12) 0.1669(14) 0.6208(4) 0.0323(17) Uani 0.733(4) 1 d D . P A 1
H23A H 0.055701 0.151399 0.589347 0.049 Uiso 0.733(4) 1 calc GR . P A 1
H23B H 0.001222 0.240271 0.628398 0.049 Uiso 0.733(4) 1 calc GR . P A 1
H23C H 0.061141 0.064432 0.635122 0.049 Uiso 0.733(4) 1 calc GR . P A 1
C7 C 0.6962(3) 0.3775(3) 0.73575(9) 0.0326(6) Uani 1 1 d . . . . .
H7 H 0.720073 0.383604 0.766310 0.039 Uiso 1 1 calc R . . . .
C11 C 0.6820(3) 0.8930(3) 0.54102(10) 0.0284(6) Uani 1 1 d . . . . .
C12 C 0.7059(3) 0.8999(3) 0.58597(9) 0.0267(6) Uani 1 1 d . . . . .
H12 H 0.779876 0.959949 0.599663 0.032 Uiso 1 1 calc R . . . .
C20A C -0.0137(8) 0.6128(10) 0.64496(19) 0.0346(12) Uani 0.733(4) 1 d D . P A 1
H20A H 0.060721 0.657892 0.664993 0.052 Uiso 0.733(4) 1 calc GR . P A 1
H20B H -0.044831 0.515287 0.657402 0.052 Uiso 0.733(4) 1 calc GR . P A 1
H20C H -0.087008 0.689879 0.640081 0.052 Uiso 0.733(4) 1 calc GR . P A 1
C6 C 0.7702(3) 0.2800(4) 0.71247(10) 0.0339(7) Uani 1 1 d . . . . .
C25A C 0.2193(14) 0.2968(15) 0.6825(2) 0.0305(18) Uani 0.733(4) 1 d D . P A 1
H25A H 0.201427 0.208299 0.701201 0.046 Uiso 0.733(4) 1 calc GR . P A 1
H25B H 0.152775 0.380667 0.683705 0.046 Uiso 0.733(4) 1 calc GR . P A 1
H25C H 0.308738 0.339301 0.692528 0.046 Uiso 0.733(4) 1 calc GR . P A 1
C19 C 0.6583(3) 0.8401(3) 0.66046(10) 0.0321(7) Uani 1 1 d . . . . .
H19A H 0.580845 0.883694 0.671762 0.048 Uiso 1 1 calc GR . . . .
H19B H 0.734308 0.912529 0.667415 0.048 Uiso 1 1 calc GR . . . .
H19C H 0.681267 0.736129 0.673677 0.048 Uiso 1 1 calc GR . . . .
C8 C 0.5882(3) 0.4666(3) 0.71571(9) 0.0278(6) Uani 1 1 d . . . . .
C5 C 0.7322(3) 0.2720(3) 0.66808(9) 0.0294(6) Uani 1 1 d . . . . .
H5 H 0.781244 0.205165 0.651730 0.035 Uiso 1 1 calc R . . . .
C16 C 0.5125(3) 0.5700(4) 0.74319(10) 0.0340(7) Uani 1 1 d . . . . .
H16A H 0.417404 0.542696 0.737522 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.524111 0.682026 0.735986 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.546940 0.552324 0.773864 0.051 Uiso 1 1 calc GR . . . .
C1 C 0.5515(3) 0.4572(3) 0.67043(9) 0.0244(6) Uani 1 1 d . . . . .
C15 C 0.8868(4) 0.1835(4) 0.73461(12) 0.0479(9) Uani 1 1 d . . . . .
H15A H 0.949619 0.253619 0.752663 0.072 Uiso 1 1 calc GR . . . .
H15B H 0.932167 0.132422 0.712722 0.072 Uiso 1 1 calc GR . . . .
H15C H 0.854403 0.101895 0.752809 0.072 Uiso 1 1 calc GR . . . .
C18 C 0.7693(3) 0.9766(4) 0.51346(10) 0.0362(7) Uani 1 1 d . . . . .
H18A H 0.825193 0.898507 0.501386 0.054 Uiso 1 1 calc GR . . . .
H18B H 0.826444 1.053390 0.531183 0.054 Uiso 1 1 calc GR . . . .
H18C H 0.713286 1.032513 0.489817 0.054 Uiso 1 1 calc GR . . . .
C22A C 0.0806(15) 0.7611(12) 0.5670(5) 0.0313(17) Uani 0.733(4) 1 d D . P A 1
H22A H 0.007216 0.835542 0.568781 0.047 Uiso 0.733(4) 1 calc GR . P A 1
H22B H 0.089955 0.744462 0.536606 0.047 Uiso 0.733(4) 1 calc GR . P A 1
H22C H 0.163821 0.805013 0.582671 0.047 Uiso 0.733(4) 1 calc GR . P A 1
C21A C -0.0980(6) 0.4735(10) 0.5542(3) 0.0369(13) Uani 0.733(4) 1 d D . P A 1
H21A H -0.129378 0.378097 0.567515 0.055 Uiso 0.733(4) 1 calc GR . P A 1
H21B H -0.067066 0.444514 0.526997 0.055 Uiso 0.733(4) 1 calc GR . P A 1
H21C H -0.171428 0.550109 0.548172 0.055 Uiso 0.733(4) 1 calc GR . P A 1
P1A P 0.2271(6) 0.4079(5) 0.59517(19) 0.0225(6) Uani 0.733(4) 1 d D . P A 1
P1B P 0.2113(17) 0.4449(14) 0.5913(6) 0.028(2) Uani 0.267(4) 1 d D . P A 2
Si1B Si 0.1994(14) 0.2478(19) 0.6399(5) 0.033(3) Uani 0.267(4) 1 d D . P A 2
C3B C 0.050(3) 0.569(3) 0.5913(7) 0.0246(3) Uani 0.267(4) 1 d D . P A 2
C20B C 0.345(2) 0.135(3) 0.6339(11) 0.0267(12) Uani 0.267(4) 1 d D . P A 2
H20D H 0.421717 0.177203 0.653338 0.040 Uiso 0.267(4) 1 calc GR . P A 2
H20E H 0.361073 0.141596 0.603920 0.040 Uiso 0.267(4) 1 calc GR . P A 2
H20F H 0.330605 0.023376 0.641310 0.040 Uiso 0.267(4) 1 calc GR . P A 2
C22B C 0.050(4) 0.130(4) 0.6271(14) 0.051(8) Uani 0.267(4) 1 d D . P A 2
H22D H 0.053402 0.040800 0.647450 0.077 Uiso 0.267(4) 1 calc GR . P A 2
H22E H 0.044069 0.088594 0.597518 0.077 Uiso 0.267(4) 1 calc GR . P A 2
H22F H -0.028162 0.195842 0.629309 0.077 Uiso 0.267(4) 1 calc GR . P A 2
C21B C 0.220(4) 0.287(4) 0.6970(7) 0.035(5) Uani 0.267(4) 1 d D . P A 2
H21D H 0.158058 0.370030 0.702838 0.053 Uiso 0.267(4) 1 calc GR . P A 2
H21E H 0.312221 0.321586 0.707021 0.053 Uiso 0.267(4) 1 calc GR . P A 2
H21F H 0.202461 0.189307 0.712401 0.053 Uiso 0.267(4) 1 calc GR . P A 2
C25B C 0.004(3) 0.590(3) 0.6348(7) 0.0346(12) Uani 0.267(4) 1 d D . P A 2
H25D H -0.015866 0.485448 0.646259 0.052 Uiso 0.267(4) 1 calc GR . P A 2
H25E H -0.077142 0.655521 0.631304 0.052 Uiso 0.267(4) 1 calc GR . P A 2
H25F H 0.074149 0.641890 0.654945 0.052 Uiso 0.267(4) 1 calc GR . P A 2
C24B C -0.063(2) 0.487(3) 0.5623(9) 0.0369(13) Uani 0.267(4) 1 d D . P A 2
H24D H -0.041561 0.480243 0.532826 0.055 Uiso 0.267(4) 1 calc GR . P A 2
H24E H -0.145634 0.548910 0.561811 0.055 Uiso 0.267(4) 1 calc GR . P A 2
H24F H -0.075821 0.380353 0.573286 0.055 Uiso 0.267(4) 1 calc GR . P A 2
C23B C 0.072(5) 0.729(4) 0.5715(15) 0.0313(17) Uani 0.267(4) 1 d D . P A 2
H23D H 0.138087 0.789854 0.591298 0.047 Uiso 0.267(4) 1 calc GR . P A 2
H23E H -0.012275 0.788297 0.566446 0.047 Uiso 0.267(4) 1 calc GR . P A 2
H23F H 0.105111 0.713823 0.543923 0.047 Uiso 0.267(4) 1 calc GR . 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
Bi1 C2 2.300(3) . ?
Bi1 C1 2.276(3) . ?
Bi1 P1A 2.686(6) . ?
Bi1 P1B 2.634(19) . ?
Si1A C20A 1.877(5) . ?
Si1A C22A 1.886(6) . ?
Si1A C21A 1.880(5) . ?
Si1A P1A 2.274(5) . ?
C3A C24A 1.533(13) . ?
C3A C23A 1.565(12) . ?
C3A C25A 1.527(13) . ?
C3A P1A 1.939(19) . ?
C2 C9 1.407(4) . ?
C2 C13 1.405(4) . ?
C9 C10 1.392(4) . ?
C9 C17 1.502(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C4 1.512(4) . ?
C13 C12 1.403(4) . ?
C13 C19 1.510(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C4 C5 1.395(4) . ?
C4 C1 1.408(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C6 1.390(4) . ?
C7 C8 1.393(4) . ?
C11 C12 1.390(4) . ?
C11 C18 1.501(4) . ?
C12 H12 0.9500 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C6 C5 1.383(4) . ?
C6 C15 1.511(4) . ?
C25A H25A 0.9800 . ?
C25A H25B 0.9800 . ?
C25A H25C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C8 C16 1.511(4) . ?
C8 C1 1.409(4) . ?
C5 H5 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
P1B Si1B 2.264(18) . ?
P1B C3B 1.94(3) . ?
Si1B C20B 1.79(2) . ?
Si1B C22B 1.80(2) . ?
Si1B C21B 1.80(2) . ?
C3B C25B 1.51(2) . ?
C3B C24B 1.51(2) . ?
C3B C23B 1.52(2) . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?

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 Bi1 P1A 106.79(14) . . ?
C2 Bi1 P1B 104.8(4) . . ?
C1 Bi1 C2 93.96(10) . . ?
C1 Bi1 P1A 98.15(11) . . ?
C1 Bi1 P1B 105.8(2) . . ?
C20A Si1A C22A 106.7(6) . . ?
C20A Si1A C21A 109.5(4) . . ?
C20A Si1A P1A 116.6(3) . . ?
C22A Si1A P1A 108.2(5) . . ?
C21A Si1A C22A 106.2(5) . . ?
C21A Si1A P1A 109.1(3) . . ?
C24A C3A C23A 108.8(11) . . ?
C24A C3A P1A 108.1(10) . . ?
C23A C3A P1A 104.4(9) . . ?
C25A C3A C24A 113.3(12) . . ?
C25A C3A C23A 108.9(13) . . ?
C25A C3A P1A 112.9(10) . . ?
C9 C2 Bi1 126.6(2) . . ?
C13 C2 Bi1 113.92(19) . . ?
C13 C2 C9 119.3(3) . . ?
C2 C9 C17 123.0(3) . . ?
C10 C9 C2 119.1(3) . . ?
C10 C9 C17 117.9(2) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
C2 C13 C19 122.8(3) . . ?
C12 C13 C2 119.0(3) . . ?
C12 C13 C19 118.2(3) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 C9 123.1(3) . . ?
C11 C10 H10 118.4 . . ?
C5 C4 C14 118.3(3) . . ?
C5 C4 C1 118.9(3) . . ?
C1 C4 C14 122.7(2) . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3A C24A H24A 109.5 . . ?
C3A C24A H24B 109.5 . . ?
C3A C24A H24C 109.5 . . ?
H24A C24A H24B 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C3A C23A H23A 109.5 . . ?
C3A C23A H23B 109.5 . . ?
C3A C23A H23C 109.5 . . ?
H23A C23A H23B 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C8 122.1(3) . . ?
C8 C7 H7 118.9 . . ?
C10 C11 C12 116.8(3) . . ?
C10 C11 C18 120.9(3) . . ?
C12 C11 C18 122.3(3) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 C13 122.7(3) . . ?
C11 C12 H12 118.7 . . ?
Si1A C20A H20A 109.5 . . ?
Si1A C20A H20B 109.5 . . ?
Si1A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C7 C6 C15 121.6(3) . . ?
C5 C6 C7 117.6(3) . . ?
C5 C6 C15 120.7(3) . . ?
C3A C25A H25A 109.5 . . ?
C3A C25A H25B 109.5 . . ?
C3A C25A H25C 109.5 . . ?
H25A C25A H25B 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 C8 C16 119.1(3) . . ?
C7 C8 C1 119.3(3) . . ?
C1 C8 C16 121.6(3) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 H5 118.7 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C1 Bi1 123.31(19) . . ?
C4 C1 C8 119.4(3) . . ?
C8 C1 Bi1 117.0(2) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1A C22A H22A 109.5 . . ?
Si1A C22A H22B 109.5 . . ?
Si1A C22A H22C 109.5 . . ?
H22A C22A H22B 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
Si1A C21A H21A 109.5 . . ?
Si1A C21A H21B 109.5 . . ?
Si1A C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
Si1A P1A Bi1 93.09(19) . . ?
C3A P1A Bi1 105.5(5) . . ?
C3A P1A Si1A 107.9(5) . . ?
Si1B P1B Bi1 98.0(7) . . ?
C3B P1B Bi1 100.9(9) . . ?
C3B P1B Si1B 105.2(11) . . ?
C20B Si1B P1B 101.0(13) . . ?
C20B Si1B C22B 111.1(19) . . ?
C20B Si1B C21B 103.1(19) . . ?
C22B Si1B P1B 112.6(12) . . ?
C21B Si1B P1B 121.5(13) . . ?
C21B Si1B C22B 107(2) . . ?
C25B C3B P1B 116.0(19) . . ?
C25B C3B C24B 106(2) . . ?
C25B C3B C23B 111(3) . . ?
C24B C3B P1B 108.4(18) . . ?
C24B C3B C23B 108(3) . . ?
C23B C3B P1B 107(2) . . ?
Si1B C20B H20D 109.5 . . ?
Si1B C20B H20E 109.5 . . ?
Si1B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
Si1B C22B H22D 109.5 . . ?
Si1B C22B H22E 109.5 . . ?
Si1B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
Si1B C21B H21D 109.5 . . ?
Si1B C21B H21E 109.5 . . ?
Si1B C21B H21F 109.5 . . ?
H21D C21B H21E 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C3B C25B H25D 109.5 . . ?
C3B C25B H25E 109.5 . . ?
C3B C25B H25F 109.5 . . ?
H25D C25B H25E 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
C3B C24B H24D 109.5 . . ?
C3B C24B H24E 109.5 . . ?
C3B C24B H24F 109.5 . . ?
H24D C24B H24E 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C3B C23B H23D 109.5 . . ?
C3B C23B H23E 109.5 . . ?
C3B C23B H23F 109.5 . . ?
H23D C23B H23E 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Heat-sensitive
####################################################################### 
# 
# 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_pcrx99
_database_code_depnum_ccdc_archive 'CCDC 2151509'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H40 As Bi Si'
_chemical_formula_sum            'C25 H40 As Bi Si'
_chemical_formula_weight         652.56
_chemical_melting_point          ?
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'
As As 0.0499 2.0058 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.1538(3)
_cell_length_b                   8.4878(2)
_cell_length_c                   31.1727(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.745(2)
_cell_angle_gamma                90
_cell_volume                     2655.34(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    39217
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.03
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.930
_exptl_absorpt_correction_T_max  0.0148
_exptl_absorpt_correction_T_min  0.0081
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.83.8.0 (STOE, 2020)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.1739
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            15324
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.976
_diffrn_reflns_theta_min         2.029
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'STOE IPDS 2T'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5369
_reflns_number_total             6248
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.025
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         6248
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+3.7667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0669
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Si1A-C21A \\sim Si1A-C22A \\sim Si1A-C20A
 with sigma of 0.02
 C23A-C3A \\sim C25A-C3A \\sim C3A-C24A
 with sigma of 0.02
 Si1B-C23B \\sim Si1B-C25B \\sim Si1B-C24B
 with sigma of 0.02
 C3B-C21B \\sim C3B-C22B \\sim C3B-C20B
 with sigma of 0.02
 As1B-C3B \\sim As1A-C3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3B) \\sim Ueq, Uanis(C3A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.02
Uanis(C21A) = Uanis(C22A) = Uanis(C20A)
Uanis(C23A) = Uanis(C25A) = Uanis(C24A)
Uanis(C23B) = Uanis(C25B) = Uanis(C24B)
Uanis(C21B) = Uanis(C22B) = Uanis(C20B)
4. Others
 Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C20B)=Sof(H20A)=Sof(H20B)=
 Sof(H20C)=Sof(C23B)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C25B)=Sof(H25A)=
 Sof(H25B)=Sof(H25C)=Sof(C22B)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C21B)=
 Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C3B)=Sof(Si1B)=Sof(As1B)=1-FVAR(1)
 Sof(Si1A)=Sof(C3A)=Sof(As1A)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C25A)=Sof(H25D)=
 Sof(H25E)=Sof(H25F)=Sof(C24B)=Sof(H24D)=Sof(H24E)=Sof(H24F)=FVAR(1)
5.a Me refined with riding coordinates:
 C21B(H21A,H21B,H21C)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C10(H10), C12(H12)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C24A(H24A,H24B,
 H24C), C20B(H20A,H20B,H20C), C14(H14A,H14B,H14C), C23B(H23A,H23B,H23C),
 C25B(H25A,H25B,H25C), C22B(H22A,H22B,H22C), C18(H18A,H18B,H18C), C15(H15A,H15B,
 H15C), C21A(H21D,H21E,H21F), C20A(H20D,H20E,H20F), C22A(H22D,H22E,H22F),
 C23A(H23D,H23E,H23F), C25A(H25D,H25E,H25F), C24B(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.38892(2) 0.37857(2) 0.63812(2) 0.02318(5) Uani 1 1 d . . . . .
Si1A Si 0.0365(6) 0.4352(6) 0.59053(14) 0.0219(14) Uani 0.601(5) 1 d D . P A 1
C3A C 0.2044(16) 0.766(3) 0.6351(7) 0.018(4) Uani 0.601(5) 1 d D U P A 1
C8 C 0.6220(4) 0.6459(4) 0.64631(12) 0.0242(7) Uani 1 1 d . . . . .
C2 C 0.5195(3) 0.2716(4) 0.59179(13) 0.0232(7) Uani 1 1 d . . . . .
C17 C 0.6612(4) 0.1680(5) 0.66054(13) 0.0298(8) Uani 1 1 d . . . . .
H17A H 0.684660 0.271996 0.673080 0.045 Uiso 1 1 calc GR . . . .
H17B H 0.736901 0.096215 0.667799 0.045 Uiso 1 1 calc GR . . . .
H17C H 0.584088 0.126519 0.672363 0.045 Uiso 1 1 calc GR . . . .
C16 C 0.5917(4) 0.6632(5) 0.59799(13) 0.0303(8) Uani 1 1 d . . . . .
H16A H 0.639850 0.754400 0.588884 0.045 Uiso 1 1 calc GR . . . .
H16B H 0.495716 0.678721 0.589345 0.045 Uiso 1 1 calc GR . . . .
H16C H 0.619779 0.567867 0.584123 0.045 Uiso 1 1 calc GR . . . .
C7 C 0.7274(4) 0.7325(5) 0.66850(14) 0.0293(8) Uani 1 1 d . . . . .
H7 H 0.775220 0.801790 0.652533 0.035 Uiso 1 1 calc R . . . .
C9 C 0.6273(4) 0.1822(4) 0.61197(13) 0.0243(7) Uani 1 1 d . . . . .
C5 C 0.6917(4) 0.6231(5) 0.73591(13) 0.0321(9) Uani 1 1 d . . . . .
H5 H 0.715356 0.615258 0.766517 0.038 Uiso 1 1 calc R . . . .
C11 C 0.6840(4) 0.1070(4) 0.54149(14) 0.0276(8) Uani 1 1 d . . . . .
C1 C 0.5496(4) 0.5454(4) 0.67008(12) 0.0231(7) Uani 1 1 d . . . . .
C19 C 0.3804(4) 0.3715(5) 0.52169(14) 0.0326(9) Uani 1 1 d . . . . .
H19A H 0.297137 0.345459 0.532393 0.049 Uiso 1 1 calc GR . . . .
H19B H 0.371712 0.346215 0.490709 0.049 Uiso 1 1 calc GR . . . .
H19C H 0.399099 0.484135 0.525941 0.049 Uiso 1 1 calc GR . . . .
C10 C 0.7077(4) 0.1025(4) 0.58618(14) 0.0272(8) Uani 1 1 d . . . . .
H10 H 0.781392 0.043107 0.600079 0.033 Uiso 1 1 calc R . . . .
C12 C 0.5749(4) 0.1951(4) 0.52208(13) 0.0266(8) Uani 1 1 d . . . . .
H12 H 0.555748 0.199297 0.491312 0.032 Uiso 1 1 calc R . . . .
C13 C 0.4934(4) 0.2767(4) 0.54642(13) 0.0244(7) Uani 1 1 d . . . . .
C24A C 0.311(2) 0.889(3) 0.6308(9) 0.0339(14) Uani 0.399(5) 1 d D . P A 1
H24A H 0.398601 0.838464 0.634527 0.051 Uiso 0.399(5) 1 calc GR . P A 1
H24B H 0.309859 0.970377 0.653137 0.051 Uiso 0.399(5) 1 calc GR . P A 1
H24C H 0.292912 0.937965 0.602020 0.051 Uiso 0.399(5) 1 calc GR . P A 1
C4 C 0.5840(4) 0.5354(5) 0.71517(13) 0.0284(8) Uani 1 1 d . . . . .
C20B C 0.0071(15) 0.416(2) 0.6373(6) 0.044(3) Uani 0.399(5) 1 d D . P A 2
H20A H 0.007930 0.517051 0.652411 0.066 Uiso 0.399(5) 1 calc GR . P A 2
H20B H 0.070062 0.343468 0.654235 0.066 Uiso 0.399(5) 1 calc GR . P A 2
H20C H -0.082724 0.370649 0.633966 0.066 Uiso 0.399(5) 1 calc GR . P A 2
C6 C 0.7649(4) 0.7214(5) 0.71288(14) 0.0324(9) Uani 1 1 d . . . . .
C14 C 0.5103(4) 0.4313(6) 0.74241(14) 0.0353(9) Uani 1 1 d . . . . .
H14A H 0.523593 0.320690 0.735092 0.053 Uiso 1 1 calc GR . . . .
H14B H 0.415001 0.456331 0.736737 0.053 Uiso 1 1 calc GR . . . .
H14C H 0.544115 0.448806 0.773190 0.053 Uiso 1 1 calc GR . . . .
C23B C 0.0465(14) 0.8806(15) 0.6274(5) 0.0327(17) Uani 0.399(5) 1 d D . P A 2
H23A H -0.027686 0.815205 0.633835 0.049 Uiso 0.399(5) 1 calc GR . P A 2
H23B H 0.033183 0.906654 0.596457 0.049 Uiso 0.399(5) 1 calc GR . P A 2
H23C H 0.050019 0.977932 0.644509 0.049 Uiso 0.399(5) 1 calc GR . P A 2
C25B C 0.2186(15) 0.7128(17) 0.6980(4) 0.0327(17) Uani 0.399(5) 1 d D . P A 2
H25A H 0.200155 0.803116 0.715745 0.049 Uiso 0.399(5) 1 calc GR . P A 2
H25B H 0.309274 0.674653 0.707808 0.049 Uiso 0.399(5) 1 calc GR . P A 2
H25C H 0.154705 0.628386 0.700925 0.049 Uiso 0.399(5) 1 calc GR . P A 2
C22B C -0.0737(13) 0.528(2) 0.5626(6) 0.044(3) Uani 0.399(5) 1 d D . P A 2
H22A H -0.152805 0.460615 0.560596 0.066 Uiso 0.399(5) 1 calc GR . P A 2
H22B H -0.053148 0.548653 0.533413 0.066 Uiso 0.399(5) 1 calc GR . P A 2
H22C H -0.091037 0.627926 0.576491 0.066 Uiso 0.399(5) 1 calc GR . P A 2
C18 C 0.7703(4) 0.0205(5) 0.51405(15) 0.0361(10) Uani 1 1 d . . . . .
H18A H 0.830855 0.095146 0.503072 0.054 Uiso 1 1 calc GR . . . .
H18B H 0.713899 -0.029853 0.489570 0.054 Uiso 1 1 calc GR . . . .
H18C H 0.822381 -0.060100 0.531658 0.054 Uiso 1 1 calc GR . . . .
C21B C 0.066(2) 0.271(2) 0.5705(8) 0.044(3) Uani 0.399(5) 1 d D . P A 2
H21A H 0.092173 0.282781 0.541678 0.066 Uiso 0.399(5) 1 calc R . P A 2
H21B H 0.134822 0.212435 0.589399 0.066 Uiso 0.399(5) 1 calc R . P A 2
H21C H -0.018789 0.214507 0.568023 0.066 Uiso 0.399(5) 1 calc R . P A 2
C15 C 0.8798(5) 0.8183(6) 0.73614(17) 0.0466(12) Uani 1 1 d . . . . .
H15A H 0.929315 0.865578 0.714749 0.070 Uiso 1 1 calc GR . . . .
H15B H 0.939360 0.750034 0.755685 0.070 Uiso 1 1 calc GR . . . .
H15C H 0.844880 0.901748 0.752990 0.070 Uiso 1 1 calc GR . . . .
C3B C 0.049(3) 0.442(3) 0.5908(6) 0.016(7) Uani 0.399(5) 1 d D U P A 2
Si1B Si 0.2031(7) 0.7725(14) 0.6415(3) 0.0228(17) Uani 0.399(5) 1 d D . P A 2
As1A As 0.2274(5) 0.6024(4) 0.59129(16) 0.0212(4) Uani 0.601(5) 1 d D . P A 1
As1B As 0.2119(8) 0.5692(6) 0.5885(3) 0.0237(7) Uani 0.399(5) 1 d D . P A 2
C21A C 0.0755(15) 0.2458(14) 0.5660(5) 0.0324(13) Uani 0.601(5) 1 d D . P A 1
H21D H 0.087960 0.263318 0.535761 0.049 Uiso 0.601(5) 1 calc GR . P A 1
H21E H 0.001774 0.171896 0.566792 0.049 Uiso 0.601(5) 1 calc GR . P A 1
H21F H 0.157328 0.201921 0.582293 0.049 Uiso 0.601(5) 1 calc GR . P A 1
C20A C -0.0151(10) 0.3932(13) 0.6434(3) 0.0324(13) Uani 0.601(5) 1 d D . P A 1
H20D H 0.062171 0.357832 0.663814 0.049 Uiso 0.601(5) 1 calc GR . P A 1
H20E H -0.083161 0.310354 0.639903 0.049 Uiso 0.601(5) 1 calc GR . P A 1
H20F H -0.051898 0.488902 0.654520 0.049 Uiso 0.601(5) 1 calc GR . P A 1
C22A C -0.1058(8) 0.5216(12) 0.5538(3) 0.0324(13) Uani 0.601(5) 1 d D . P A 1
H22D H -0.132761 0.620492 0.566151 0.049 Uiso 0.601(5) 1 calc GR . P A 1
H22E H -0.180784 0.447593 0.550348 0.049 Uiso 0.601(5) 1 calc GR . P A 1
H22F H -0.079213 0.542379 0.525375 0.049 Uiso 0.601(5) 1 calc GR . P A 1
C23A C 0.0653(10) 0.8424(10) 0.6214(3) 0.0339(14) Uani 0.601(5) 1 d D . P A 1
H23D H 0.057320 0.936532 0.639044 0.051 Uiso 0.601(5) 1 calc GR . P A 1
H23E H -0.004204 0.766632 0.625838 0.051 Uiso 0.601(5) 1 calc GR . P A 1
H23F H 0.054980 0.871995 0.590697 0.051 Uiso 0.601(5) 1 calc GR . P A 1
C25A C 0.2185(10) 0.7100(11) 0.6829(3) 0.0339(14) Uani 0.601(5) 1 d D . P A 1
H25D H 0.306964 0.663704 0.691515 0.051 Uiso 0.601(5) 1 calc GR . P A 1
H25E H 0.150067 0.630779 0.685685 0.051 Uiso 0.601(5) 1 calc GR . P A 1
H25F H 0.207299 0.799890 0.701778 0.051 Uiso 0.601(5) 1 calc GR . P A 1
C24B C 0.3313(11) 0.9085(15) 0.6337(5) 0.0327(17) Uani 0.601(5) 1 d D . P A 2
H24D H 0.326296 0.931579 0.602736 0.049 Uiso 0.601(5) 1 calc GR . P A 2
H24E H 0.418482 0.862541 0.644737 0.049 Uiso 0.601(5) 1 calc GR . P A 2
H24F H 0.319678 1.006218 0.649504 0.049 Uiso 0.601(5) 1 calc GR . 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
Bi1 C2 2.291(4) . ?
Bi1 C1 2.273(4) . ?
Bi1 As1A 2.776(5) . ?
Bi1 As1B 2.719(8) . ?
Si1A As1A 2.399(8) . ?
Si1A C21A 1.849(9) . ?
Si1A C20A 1.837(9) . ?
Si1A C22A 1.854(9) . ?
C3A C24A 1.523(17) . ?
C3A As1A 1.99(3) . ?
C3A C23A 1.552(16) . ?
C3A C25A 1.551(16) . ?
C8 C16 1.498(5) . ?
C8 C7 1.392(6) . ?
C8 C1 1.408(5) . ?
C2 C9 1.400(5) . ?
C2 C13 1.399(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C9 1.506(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C6 1.381(6) . ?
C9 C10 1.404(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.398(6) . ?
C5 C6 1.388(6) . ?
C11 C10 1.378(6) . ?
C11 C12 1.396(5) . ?
C11 C18 1.506(6) . ?
C1 C4 1.398(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C13 1.513(5) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.390(5) . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C4 C14 1.502(6) . ?
C20B H20A 0.9800 . ?
C20B H20B 0.9800 . ?
C20B H20C 0.9800 . ?
C20B C3B 1.590(19) . ?
C6 C15 1.518(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C23B H23A 0.9800 . ?
C23B H23B 0.9800 . ?
C23B H23C 0.9800 . ?
C23B Si1B 1.831(13) . ?
C25B H25A 0.9800 . ?
C25B H25B 0.9800 . ?
C25B H25C 0.9800 . ?
C25B Si1B 1.816(13) . ?
C22B H22A 0.9800 . ?
C22B H22B 0.9800 . ?
C22B H22C 0.9800 . ?
C22B C3B 1.593(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21B H21A 0.9800 . ?
C21B H21B 0.9800 . ?
C21B H21C 0.9800 . ?
C21B C3B 1.596(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3B As1B 1.98(3) . ?
Si1B As1B 2.400(15) . ?
Si1B C24B 1.784(10) . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?

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 Bi1 As1A 106.98(14) . . ?
C2 Bi1 As1B 105.8(2) . . ?
C1 Bi1 C2 94.46(13) . . ?
C1 Bi1 As1A 97.56(12) . . ?
C1 Bi1 As1B 104.29(14) . . ?
C21A Si1A As1A 107.2(6) . . ?
C21A Si1A C22A 106.5(7) . . ?
C20A Si1A As1A 116.5(4) . . ?
C20A Si1A C21A 108.1(7) . . ?
C20A Si1A C22A 109.2(6) . . ?
C22A Si1A As1A 109.0(4) . . ?
C24A C3A As1A 105.0(15) . . ?
C24A C3A C23A 108.7(17) . . ?
C24A C3A C25A 109.5(18) . . ?
C23A C3A As1A 107.3(12) . . ?
C25A C3A As1A 116.1(14) . . ?
C25A C3A C23A 109.9(14) . . ?
C7 C8 C16 118.2(4) . . ?
C7 C8 C1 118.8(4) . . ?
C1 C8 C16 123.0(3) . . ?
C9 C2 Bi1 114.8(3) . . ?
C13 C2 Bi1 125.9(3) . . ?
C13 C2 C9 119.1(3) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C7 H7 118.8 . . ?
C6 C7 C8 122.4(4) . . ?
C6 C7 H7 118.8 . . ?
C2 C9 C17 122.6(3) . . ?
C2 C9 C10 119.1(4) . . ?
C10 C9 C17 118.2(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C6 C5 C4 121.6(4) . . ?
C10 C11 C12 117.3(4) . . ?
C10 C11 C18 122.2(4) . . ?
C12 C11 C18 120.5(4) . . ?
C8 C1 Bi1 123.0(3) . . ?
C4 C1 Bi1 117.1(3) . . ?
C4 C1 C8 119.7(4) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.6(4) . . ?
C11 C10 H10 118.7 . . ?
C11 C12 H12 119.0 . . ?
C13 C12 C11 122.0(4) . . ?
C13 C12 H12 119.0 . . ?
C2 C13 C19 122.9(3) . . ?
C12 C13 C2 120.0(3) . . ?
C12 C13 C19 117.1(4) . . ?
C3A C24A H24A 109.5 . . ?
C3A C24A H24B 109.5 . . ?
C3A C24A H24C 109.5 . . ?
H24A C24A H24B 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C5 C4 C1 119.4(4) . . ?
C5 C4 C14 118.3(4) . . ?
C1 C4 C14 122.3(4) . . ?
H20A C20B H20B 109.5 . . ?
H20A C20B H20C 109.5 . . ?
H20B C20B H20C 109.5 . . ?
C3B C20B H20A 109.5 . . ?
C3B C20B H20B 109.5 . . ?
C3B C20B H20C 109.5 . . ?
C7 C6 C5 118.1(4) . . ?
C7 C6 C15 121.1(4) . . ?
C5 C6 C15 120.8(4) . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H23A C23B H23B 109.5 . . ?
H23A C23B H23C 109.5 . . ?
H23B C23B H23C 109.5 . . ?
Si1B C23B H23A 109.5 . . ?
Si1B C23B H23B 109.5 . . ?
Si1B C23B H23C 109.5 . . ?
H25A C25B H25B 109.5 . . ?
H25A C25B H25C 109.5 . . ?
H25B C25B H25C 109.5 . . ?
Si1B C25B H25A 109.5 . . ?
Si1B C25B H25B 109.5 . . ?
Si1B C25B H25C 109.5 . . ?
H22A C22B H22B 109.5 . . ?
H22A C22B H22C 109.5 . . ?
H22B C22B H22C 109.5 . . ?
C3B C22B H22A 109.5 . . ?
C3B C22B H22B 109.5 . . ?
C3B C22B H22C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H21A C21B H21B 109.5 . . ?
H21A C21B H21C 109.5 . . ?
H21B C21B H21C 109.5 . . ?
C3B C21B H21A 109.5 . . ?
C3B C21B H21B 109.5 . . ?
C3B C21B H21C 109.5 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C20B C3B C22B 105.5(17) . . ?
C20B C3B C21B 107(2) . . ?
C20B C3B As1B 116.7(15) . . ?
C22B C3B C21B 109(2) . . ?
C22B C3B As1B 108.5(14) . . ?
C21B C3B As1B 110.0(17) . . ?
C23B Si1B As1B 108.5(6) . . ?
C25B Si1B C23B 108.4(9) . . ?
C25B Si1B As1B 117.4(7) . . ?
C24B Si1B C23B 105.6(9) . . ?
C24B Si1B C25B 110.8(10) . . ?
C24B Si1B As1B 105.5(7) . . ?
Si1A As1A Bi1 90.70(16) . . ?
C3A As1A Bi1 103.9(4) . . ?
C3A As1A Si1A 104.0(6) . . ?
C3B As1B Bi1 97.8(6) . . ?
C3B As1B Si1B 104.5(7) . . ?
Si1B As1B Bi1 97.3(3) . . ?
Si1A C21A H21D 109.5 . . ?
Si1A C21A H21E 109.5 . . ?
Si1A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
Si1A C20A H20D 109.5 . . ?
Si1A C20A H20E 109.5 . . ?
Si1A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
Si1A C22A H22D 109.5 . . ?
Si1A C22A H22E 109.5 . . ?
Si1A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C3A C23A H23D 109.5 . . ?
C3A C23A H23E 109.5 . . ?
C3A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C3A C25A H25D 109.5 . . ?
C3A C25A H25E 109.5 . . ?
C3A C25A H25F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
Si1B C24B H24D 109.5 . . ?
Si1B C24B H24E 109.5 . . ?
Si1B C24B H24F 109.5 . . ?
H24D C24B H24E 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx002
_database_code_depnum_ccdc_archive 'CCDC 2151502'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2020-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H40 As Bi'
_chemical_formula_sum            'C26 H40 As Bi'
_chemical_formula_weight         636.48
_chemical_melting_point          ?
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'
As As 0.0499 2.0058 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.010(2)
_cell_length_b                   8.3035(19)
_cell_length_c                   30.855(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.675(16)
_cell_angle_gamma                90
_cell_volume                     2541.7(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    30507
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      51.998
_cell_measurement_theta_min      2.664
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.238
_exptl_absorpt_correction_T_max  0.7488
_exptl_absorpt_correction_T_min  0.1208
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'X-Area LANA 1.76.6.0 (STOE, 2019)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0696
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            23780
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.332
_diffrn_ambient_temperature      100
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           0.000
_diffrn_source_power             0.000
_diffrn_source_voltage           0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4425
_reflns_number_total             4994
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.790
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.0869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0641
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C11(H11), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,
 H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C),
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
As1 As 0.61714(4) 0.58621(5) 0.40986(2) 0.02683(9) Uani 1 1 d . . . . .
Bi1 Bi 0.75353(2) 0.37580(2) 0.36102(2) 0.02552(6) Uani 1 1 d . . . . .
C1 C 0.9297(3) 0.2702(4) 0.40773(12) 0.0270(7) Uani 1 1 d . . . . .
C2 C 0.8857(3) 0.5484(4) 0.32787(11) 0.0252(7) Uani 1 1 d . . . . .
C3 C 0.4516(4) 0.4414(5) 0.40936(12) 0.0321(8) Uani 1 1 d . . . . .
C4 C 0.5669(4) 0.7664(4) 0.36565(12) 0.0312(8) Uani 1 1 d . . . . .
C5 C 0.8747(3) 0.5416(4) 0.28190(11) 0.0281(7) Uani 1 1 d . . . . .
C6 C 0.9644(4) 0.6285(4) 0.26033(12) 0.0301(8) Uani 1 1 d . . . . .
H6 H 0.957024 0.622714 0.229348 0.036 Uiso 1 1 calc R . . . .
C7 C 1.0651(4) 0.7239(5) 0.28301(12) 0.0329(8) Uani 1 1 d . . . . .
C8 C 1.0727(3) 0.7321(5) 0.32806(12) 0.0295(8) Uani 1 1 d . . . . .
H8 H 1.139373 0.798829 0.343835 0.035 Uiso 1 1 calc R . . . .
C9 C 0.9849(4) 0.6448(4) 0.35122(12) 0.0262(7) Uani 1 1 d . . . . .
C10 C 1.0221(4) 0.1796(4) 0.38686(11) 0.0272(7) Uani 1 1 d . . . . .
C11 C 1.1274(4) 0.0996(4) 0.41249(13) 0.0300(8) Uani 1 1 d . . . . .
H11 H 1.189355 0.038948 0.398296 0.036 Uiso 1 1 calc R . . . .
C12 C 1.1449(4) 0.1053(4) 0.45794(13) 0.0295(8) Uani 1 1 d . . . . .
C13 C 1.0519(3) 0.1954(4) 0.47752(11) 0.0280(7) Uani 1 1 d . . . . .
H13 H 1.061094 0.200376 0.508537 0.034 Uiso 1 1 calc R . . . .
C14 C 0.9456(3) 0.2784(4) 0.45344(11) 0.0278(7) Uani 1 1 d . . . . .
C15 C 0.7693(4) 0.4410(5) 0.25528(12) 0.0344(8) Uani 1 1 d . . . . .
H15A H 0.788170 0.326669 0.261147 0.052 Uiso 1 1 calc GR . . . .
H15B H 0.770487 0.462864 0.224125 0.052 Uiso 1 1 calc GR . . . .
H15C H 0.680302 0.467774 0.263201 0.052 Uiso 1 1 calc GR . . . .
C16 C 1.0023(4) 0.6593(5) 0.40035(12) 0.0294(8) Uani 1 1 d . . . . .
H16A H 0.913596 0.662754 0.410425 0.044 Uiso 1 1 calc GR . . . .
H16B H 1.051881 0.758294 0.409196 0.044 Uiso 1 1 calc GR . . . .
H16C H 1.052864 0.566180 0.413370 0.044 Uiso 1 1 calc GR . . . .
C17 C 1.1611(4) 0.8200(5) 0.25906(13) 0.0412(10) Uani 1 1 d . . . . .
H17A H 1.194265 0.751835 0.236861 0.062 Uiso 1 1 calc GR . . . .
H17B H 1.237295 0.856976 0.279934 0.062 Uiso 1 1 calc GR . . . .
H17C H 1.113718 0.913249 0.244880 0.062 Uiso 1 1 calc GR . . . .
C18 C 1.0125(4) 0.1652(5) 0.33775(12) 0.0346(8) Uani 1 1 d . . . . .
H18A H 0.925730 0.116966 0.326143 0.052 Uiso 1 1 calc GR . . . .
H18B H 1.085923 0.096881 0.330258 0.052 Uiso 1 1 calc GR . . . .
H18C H 1.019706 0.272395 0.324970 0.052 Uiso 1 1 calc GR . . . .
C19 C 0.8559(4) 0.3758(4) 0.47875(12) 0.0316(8) Uani 1 1 d . . . . .
H19A H 0.876811 0.350905 0.509970 0.047 Uiso 1 1 calc GR . . . .
H19B H 0.761434 0.349167 0.468724 0.047 Uiso 1 1 calc GR . . . .
H19C H 0.870882 0.490732 0.474068 0.047 Uiso 1 1 calc GR . . . .
C20 C 1.2582(4) 0.0196(5) 0.48543(13) 0.0372(9) Uani 1 1 d . . . . .
H20A H 1.330635 0.096290 0.494944 0.056 Uiso 1 1 calc GR . . . .
H20B H 1.292939 -0.066156 0.468169 0.056 Uiso 1 1 calc GR . . . .
H20C H 1.225056 -0.027384 0.511107 0.056 Uiso 1 1 calc GR . . . .
C21 C 0.6867(4) 0.8799(4) 0.37208(14) 0.0340(9) Uani 1 1 d . . . . .
H21A H 0.704127 0.912445 0.402853 0.051 Uiso 1 1 calc GR . . . .
H21B H 0.666977 0.975531 0.353712 0.051 Uiso 1 1 calc GR . . . .
H21C H 0.766257 0.825176 0.363838 0.051 Uiso 1 1 calc GR . . . .
C22 C 0.5393(4) 0.7165(5) 0.31773(12) 0.0356(9) Uani 1 1 d . . . . .
H22A H 0.621864 0.672628 0.308466 0.053 Uiso 1 1 calc GR . . . .
H22B H 0.509850 0.810582 0.299781 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.468499 0.634220 0.314137 0.053 Uiso 1 1 calc GR . . . .
C23 C 0.4436(4) 0.8526(5) 0.37915(15) 0.0382(9) Uani 1 1 d . . . . .
H23A H 0.365704 0.780085 0.375044 0.057 Uiso 1 1 calc GR . . . .
H23B H 0.424073 0.948937 0.361048 0.057 Uiso 1 1 calc GR . . . .
H23C H 0.462133 0.884055 0.409979 0.057 Uiso 1 1 calc GR . . . .
C24 C 0.3706(4) 0.4102(5) 0.36474(14) 0.0384(9) Uani 1 1 d . . . . .
H24A H 0.332294 0.511713 0.352580 0.058 Uiso 1 1 calc GR . . . .
H24B H 0.297598 0.334191 0.367909 0.058 Uiso 1 1 calc GR . . . .
H24C H 0.429780 0.364503 0.345048 0.058 Uiso 1 1 calc GR . . . .
C25 C 0.3606(4) 0.5190(5) 0.43992(14) 0.0409(10) Uani 1 1 d . . . . .
H25A H 0.412957 0.538354 0.468606 0.061 Uiso 1 1 calc GR . . . .
H25B H 0.285285 0.446547 0.443210 0.061 Uiso 1 1 calc GR . . . .
H25C H 0.325462 0.621466 0.427419 0.061 Uiso 1 1 calc GR . . . .
C26 C 0.5010(4) 0.2813(5) 0.43011(13) 0.0343(9) Uani 1 1 d . . . . .
H26A H 0.566304 0.232796 0.412984 0.052 Uiso 1 1 calc GR . . . .
H26B H 0.424301 0.208223 0.430532 0.052 Uiso 1 1 calc GR . . . .
H26C H 0.544130 0.300127 0.460096 0.052 Uiso 1 1 calc GR . . . .


_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
As1 Bi1 2.7815(6) . ?
As1 C3 2.046(4) . ?
As1 C4 2.042(4) . ?
Bi1 C1 2.298(4) . ?
Bi1 C2 2.283(3) . ?
C1 C10 1.412(5) . ?
C1 C14 1.400(5) . ?
C2 C5 1.409(5) . ?
C2 C9 1.398(5) . ?
C3 C24 1.524(5) . ?
C3 C25 1.537(5) . ?
C3 C26 1.529(5) . ?
C4 C21 1.518(5) . ?
C4 C22 1.525(5) . ?
C4 C23 1.532(5) . ?
C5 C6 1.389(5) . ?
C5 C15 1.502(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(5) . ?
C7 C8 1.383(5) . ?
C7 C17 1.515(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.406(5) . ?
C9 C16 1.508(5) . ?
C10 C11 1.398(5) . ?
C10 C18 1.510(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(5) . ?
C12 C13 1.394(5) . ?
C12 C20 1.502(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(5) . ?
C14 C19 1.503(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C3 As1 Bi1 94.73(11) . . ?
C4 As1 Bi1 101.15(10) . . ?
C4 As1 C3 107.36(15) . . ?
C1 Bi1 As1 106.94(9) . . ?
C2 Bi1 As1 101.78(9) . . ?
C2 Bi1 C1 94.50(12) . . ?
C10 C1 Bi1 114.3(2) . . ?
C14 C1 Bi1 126.0(3) . . ?
C14 C1 C10 119.5(3) . . ?
C5 C2 Bi1 117.0(2) . . ?
C9 C2 Bi1 122.9(3) . . ?
C9 C2 C5 119.7(3) . . ?
C24 C3 As1 116.1(3) . . ?
C24 C3 C25 109.8(3) . . ?
C24 C3 C26 109.5(3) . . ?
C25 C3 As1 107.1(3) . . ?
C26 C3 As1 106.9(2) . . ?
C26 C3 C25 107.0(3) . . ?
C21 C4 As1 104.4(2) . . ?
C21 C4 C22 109.4(3) . . ?
C21 C4 C23 109.0(3) . . ?
C22 C4 As1 116.5(3) . . ?
C22 C4 C23 110.0(3) . . ?
C23 C4 As1 107.3(3) . . ?
C2 C5 C15 121.8(3) . . ?
C6 C5 C2 119.6(3) . . ?
C6 C5 C15 118.6(3) . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C17 121.1(3) . . ?
C8 C7 C6 118.1(3) . . ?
C8 C7 C17 120.7(4) . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 122.1(3) . . ?
C9 C8 H8 119.0 . . ?
C2 C9 C8 118.9(3) . . ?
C2 C9 C16 122.9(3) . . ?
C8 C9 C16 118.3(3) . . ?
C1 C10 C18 122.8(3) . . ?
C11 C10 C1 119.0(3) . . ?
C11 C10 C18 118.1(3) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 C10 122.5(3) . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C13 117.0(3) . . ?
C11 C12 C20 122.5(3) . . ?
C13 C12 C20 120.5(3) . . ?
C12 C13 H13 118.6 . . ?
C12 C13 C14 122.7(3) . . ?
C14 C13 H13 118.6 . . ?
C1 C14 C19 123.7(3) . . ?
C13 C14 C1 119.2(3) . . ?
C13 C14 C19 117.1(3) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C21 H21A 109.5 . . ?
C4 C21 H21B 109.5 . . ?
C4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C23 H23A 109.5 . . ?
C4 C23 H23B 109.5 . . ?
C4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C24 H24A 109.5 . . ?
C3 C24 H24B 109.5 . . ?
C3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C3 C25 H25A 109.5 . . ?
C3 C25 H25B 109.5 . . ?
C3 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C3 C26 H26A 109.5 . . ?
C3 C26 H26B 109.5 . . ?
C3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_tdx052
_database_code_depnum_ccdc_archive 'CCDC 2151507'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H32 Bi Sb'
_chemical_formula_sum            'C30 H32 Bi Sb'
_chemical_formula_weight         723.28
_chemical_melting_point          ?
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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8036(4)
_cell_length_b                   11.5319(5)
_cell_length_c                   13.3134(5)
_cell_angle_alpha                77.045(3)
_cell_angle_beta                 75.373(3)
_cell_angle_gamma                65.976(3)
_cell_volume                     1317.59(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21290
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.255
_cell_measurement_theta_min      1.596
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.709
_exptl_absorpt_correction_T_max  0.5195
_exptl_absorpt_correction_T_min  0.1611
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.83.8.0 (STOE, 2020)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0453
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16609
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.255
_diffrn_reflns_theta_min         1.596
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'STOE IPDS 2T'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5871
_reflns_number_total             7091
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.640
_refine_diff_density_min         -1.677
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         7091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0762
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C14(H14), C18(H18), C21(H21), C5(H5), C16(H16), C12(H12), C8(H8),
 C11(H11), C10(H10), C6(H6), C9(H9), C13(H13), C7(H7)
2.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C26(H26A,H26B,
 H26C), C30(H30A,H30B,H30C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.37612(2) 0.56437(2) 0.86774(2) 0.02468(5) Uani 1 1 d . . . . .
Sb1 Sb 0.53155(3) 0.54459(3) 0.65000(2) 0.02369(7) Uani 1 1 d . . . . .
C20 C 0.5690(5) 0.8103(4) 0.6289(3) 0.0243(8) Uani 1 1 d . . . . .
C22 C 0.7520(5) 0.8798(4) 0.4966(3) 0.0280(9) Uani 1 1 d . . . . .
C23 C 0.8105(5) 0.7611(4) 0.4611(3) 0.0284(9) Uani 1 1 d . . . . .
H23 H 0.893793 0.743713 0.404213 0.034 Uiso 1 1 calc R . . . .
C4 C 0.6309(5) 0.6899(4) 0.5934(3) 0.0235(8) Uani 1 1 d . . . . .
C14 C 0.1106(5) 0.7139(4) 0.7273(3) 0.0294(9) Uani 1 1 d . . . . .
H14 H 0.192163 0.702123 0.669248 0.035 Uiso 1 1 calc R . . . .
C24 C 0.7500(5) 0.6672(4) 0.5069(3) 0.0257(8) Uani 1 1 d . . . . .
C1 C 0.3852(5) 0.3657(4) 0.8701(3) 0.0270(9) Uani 1 1 d . . . . .
C18 C 0.8386(6) 0.1523(5) 0.7335(4) 0.0345(11) Uani 1 1 d . . . . .
H18 H 0.850154 0.071365 0.719211 0.041 Uiso 1 1 calc R . . . .
C21 C 0.6307(6) 0.9023(4) 0.5794(3) 0.0283(9) Uani 1 1 d . . . . .
H21 H 0.587880 0.983521 0.603390 0.034 Uiso 1 1 calc R . . . .
C5 C 0.4982(5) 0.2631(5) 0.9150(3) 0.0319(10) Uani 1 1 d . . . . .
H5 H 0.562495 0.278530 0.948823 0.038 Uiso 1 1 calc R . . . .
C2 C 0.1411(5) 0.6652(4) 0.8284(3) 0.0249(8) Uani 1 1 d . . . . .
C16 C 0.9076(6) 0.2767(5) 0.8179(4) 0.0320(10) Uani 1 1 d . . . . .
H16 H 0.965557 0.281778 0.863000 0.038 Uiso 1 1 calc R . . . .
C12 C -0.1575(6) 0.7989(5) 0.7942(4) 0.0327(10) Uani 1 1 d . . . . .
H12 H -0.258663 0.845123 0.782587 0.039 Uiso 1 1 calc R . . . .
C8 C 0.3112(6) 0.2160(5) 0.8169(4) 0.0362(11) Uani 1 1 d . . . . .
H8 H 0.247408 0.200141 0.782941 0.043 Uiso 1 1 calc R . . . .
C29 C 0.8187(6) 0.9802(5) 0.4481(4) 0.0368(11) Uani 1 1 d . . . . .
H29A H 0.892701 0.974136 0.488483 0.055 Uiso 1 1 calc GR . . . .
H29B H 0.737588 1.065285 0.448281 0.055 Uiso 1 1 calc GR . . . .
H29C H 0.869274 0.966570 0.375774 0.055 Uiso 1 1 calc GR . . . .
C17 C 0.9239(6) 0.1562(5) 0.8006(4) 0.0355(11) Uani 1 1 d . . . . .
C25 C 0.8012(6) 0.5145(4) 0.7942(4) 0.0302(9) Uani 1 1 d . . . . .
H25A H 0.698028 0.561808 0.828751 0.045 Uiso 1 1 calc GR . . . .
H25B H 0.827643 0.565873 0.728540 0.045 Uiso 1 1 calc GR . . . .
H25C H 0.872930 0.496881 0.840349 0.045 Uiso 1 1 calc GR . . . .
C3 C 0.7186(5) 0.3828(4) 0.7065(3) 0.0268(9) Uani 1 1 d . . . . .
C11 C -0.1286(6) 0.7501(5) 0.8953(4) 0.0349(10) Uani 1 1 d . . . . .
H11 H -0.210586 0.762588 0.953080 0.042 Uiso 1 1 calc R . . . .
C15 C 0.8087(5) 0.3895(4) 0.7708(3) 0.0277(9) Uani 1 1 d . . . . .
C19 C 0.7369(5) 0.2625(4) 0.6865(3) 0.0284(9) Uani 1 1 d . . . . .
C28 C 0.4409(6) 0.8436(4) 0.7209(3) 0.0302(9) Uani 1 1 d . . . . .
H28A H 0.361528 0.815685 0.715123 0.045 Uiso 1 1 calc GR . . . .
H28B H 0.398605 0.936561 0.721308 0.045 Uiso 1 1 calc GR . . . .
H28C H 0.479181 0.800314 0.786020 0.045 Uiso 1 1 calc GR . . . .
C10 C 0.0184(5) 0.6838(5) 0.9121(3) 0.0302(9) Uani 1 1 d . . . . .
H10 H 0.036594 0.650359 0.981550 0.036 Uiso 1 1 calc R . . . .
C6 C 0.5174(6) 0.1375(5) 0.9106(4) 0.0348(10) Uani 1 1 d . . . . .
H6 H 0.594617 0.067587 0.941283 0.042 Uiso 1 1 calc R . . . .
C9 C 0.2905(6) 0.3411(5) 0.8215(3) 0.0313(10) Uani 1 1 d . . . . .
H9 H 0.211755 0.410331 0.791617 0.038 Uiso 1 1 calc R . . . .
C13 C -0.0369(6) 0.7791(5) 0.7108(4) 0.0347(10) Uani 1 1 d . . . . .
H13 H -0.055771 0.810729 0.641332 0.042 Uiso 1 1 calc R . . . .
C7 C 0.4231(6) 0.1149(5) 0.8609(4) 0.0360(10) Uani 1 1 d . . . . .
H7 H 0.436201 0.029500 0.857582 0.043 Uiso 1 1 calc R . . . .
C26 C 1.0310(7) 0.0344(5) 0.8532(4) 0.0509(15) Uani 1 1 d . . . . .
H26A H 0.977353 -0.023867 0.886579 0.076 Uiso 1 1 calc GR . . . .
H26B H 1.067159 0.055343 0.906493 0.076 Uiso 1 1 calc GR . . . .
H26C H 1.117777 -0.007207 0.800709 0.076 Uiso 1 1 calc GR . . . .
C30 C 0.8161(6) 0.5431(5) 0.4615(4) 0.0321(10) Uani 1 1 d . . . . .
H30A H 0.895438 0.547023 0.400460 0.048 Uiso 1 1 calc GR . . . .
H30B H 0.735872 0.529377 0.440078 0.048 Uiso 1 1 calc GR . . . .
H30C H 0.860081 0.472088 0.514477 0.048 Uiso 1 1 calc GR . . . .
C27 C 0.6466(6) 0.2476(5) 0.6171(4) 0.0396(12) Uani 1 1 d . . . . .
H27A H 0.662621 0.296364 0.547688 0.059 Uiso 1 1 calc GR . . . .
H27B H 0.538497 0.279823 0.648242 0.059 Uiso 1 1 calc GR . . . .
H27C H 0.680130 0.156747 0.610227 0.059 Uiso 1 1 calc GR . . . .


_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 Sb1 2.9256(3) . ?
Bi1 C1 2.250(4) . ?
Bi1 C2 2.256(4) . ?
Sb1 C4 2.172(4) . ?
Sb1 C3 2.166(5) . ?
C20 C4 1.408(6) . ?
C20 C21 1.389(6) . ?
C20 C28 1.505(6) . ?
C22 C23 1.393(6) . ?
C22 C21 1.383(7) . ?
C22 C29 1.500(6) . ?
C23 C24 1.393(6) . ?
C4 C24 1.402(6) . ?
C14 C2 1.394(6) . ?
C14 C13 1.380(7) . ?
C24 C30 1.506(6) . ?
C1 C5 1.391(7) . ?
C1 C9 1.401(6) . ?
C18 C17 1.388(8) . ?
C18 C19 1.388(7) . ?
C5 C6 1.395(7) . ?
C2 C10 1.398(6) . ?
C16 C17 1.398(7) . ?
C16 C15 1.393(7) . ?
C12 C11 1.389(7) . ?
C12 C13 1.384(7) . ?
C8 C9 1.385(7) . ?
C8 C7 1.372(7) . ?
C17 C26 1.515(7) . ?
C25 C15 1.510(6) . ?
C3 C15 1.410(6) . ?
C3 C19 1.403(6) . ?
C11 C10 1.379(7) . ?
C19 C27 1.508(7) . ?
C6 C7 1.393(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
C1 Bi1 Sb1 85.03(10) . . ?
C1 Bi1 C2 95.05(16) . . ?
C2 Bi1 Sb1 94.92(11) . . ?
C4 Sb1 Bi1 110.08(11) . . ?
C3 Sb1 Bi1 88.48(11) . . ?
C3 Sb1 C4 101.78(16) . . ?
C4 C20 C28 123.0(4) . . ?
C21 C20 C4 119.2(4) . . ?
C21 C20 C28 117.8(4) . . ?
C23 C22 C29 121.6(4) . . ?
C21 C22 C23 117.8(4) . . ?
C21 C22 C29 120.6(4) . . ?
C24 C23 C22 121.6(4) . . ?
C20 C4 Sb1 123.6(3) . . ?
C24 C4 Sb1 116.6(3) . . ?
C24 C4 C20 119.1(4) . . ?
C13 C14 C2 120.7(4) . . ?
C23 C24 C4 119.7(4) . . ?
C23 C24 C30 118.4(4) . . ?
C4 C24 C30 121.9(4) . . ?
C5 C1 Bi1 117.8(3) . . ?
C5 C1 C9 119.1(4) . . ?
C9 C1 Bi1 122.9(3) . . ?
C17 C18 C19 122.3(4) . . ?
C22 C21 C20 122.4(4) . . ?
C1 C5 C6 120.2(5) . . ?
C14 C2 Bi1 124.6(3) . . ?
C14 C2 C10 118.2(4) . . ?
C10 C2 Bi1 117.2(3) . . ?
C15 C16 C17 121.9(5) . . ?
C13 C12 C11 119.1(5) . . ?
C7 C8 C9 120.6(5) . . ?
C18 C17 C16 117.6(5) . . ?
C18 C17 C26 121.3(5) . . ?
C16 C17 C26 121.1(5) . . ?
C15 C3 Sb1 124.4(3) . . ?
C19 C3 Sb1 116.0(3) . . ?
C19 C3 C15 119.1(4) . . ?
C10 C11 C12 120.4(4) . . ?
C16 C15 C25 117.4(4) . . ?
C16 C15 C3 119.4(4) . . ?
C3 C15 C25 123.1(4) . . ?
C18 C19 C3 119.6(4) . . ?
C18 C19 C27 118.1(4) . . ?
C3 C19 C27 122.3(4) . . ?
C11 C10 C2 120.9(4) . . ?
C7 C6 C5 119.9(5) . . ?
C8 C9 C1 120.2(5) . . ?
C14 C13 C12 120.7(4) . . ?
C8 C7 C6 120.0(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_tdx045
_database_code_depnum_ccdc_archive 'CCDC 2151506'
loop_
_audit_author_name
_audit_author_address
'Carsten von Hanisch'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H40 Bi P'
_chemical_formula_sum            'C26 H40 Bi P'
_chemical_formula_weight         592.53
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   17.2923(13)
_cell_length_b                   9.4485(5)
_cell_length_c                   31.273(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.938(6)
_cell_angle_gamma                90
_cell_volume                     5072.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23579
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.914
_cell_measurement_theta_min      1.659
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.024
_exptl_absorpt_correction_T_max  0.4210
_exptl_absorpt_correction_T_min  0.1800
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.83.8.0 (STOE, 2020)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.0492
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            33120
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.914
_diffrn_reflns_theta_min         1.659
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'STOE IPDS 2T'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8976
_reflns_number_total             12063
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.646
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         12063
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+3.1493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0695
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C22(H22), C12(H12), C15(H15), C25(H25), C27(H27), C10(H10), C20(H20)
2.b Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C29(H29A,H29B,H29C), C43(H43A,H43B,H43C), C47(H47A,H47B,
 H47C), C40(H40A,H40B,H40C), C33(H33A,H33B,H33C), C37(H37A,H37B,H37C), C49(H49A,
 H49B,H49C), C48(H48A,H48B,H48C), C41(H41A,H41B,H41C), C32(H32A,H32B,H32C),
 C44(H44A,H44B,H44C), C31(H31A,H31B,H31C), C45(H45A,H45B,H45C), C50(H50A,H50B,
 H50C), C51(H51A,H51B,H51C), C30(H30A,H30B,H30C), C39(H39A,H39B,H39C), C52(H52A,
 H52B,H52C), C34(H34A,H34B,H34C), C46(H46A,H46B,H46C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.73770(2) 0.04286(2) 0.42129(2) 0.01787(4) Uani 1 1 d . . . . .
Bi2 Bi 0.80103(2) 1.03674(2) 0.24050(2) 0.02068(4) Uani 1 1 d . . . . .
P1 P 0.74772(6) -0.08662(11) 0.49773(3) 0.0180(2) Uani 1 1 d . . . . .
P2 P 0.70970(6) 1.17292(12) 0.17818(3) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.6361(2) 0.1943(4) 0.42405(13) 0.0205(8) Uani 1 1 d . . . . .
C17 C 0.8842(2) 0.3992(4) 0.38296(13) 0.0222(8) Uani 1 1 d . . . . .
H17 H 0.881773 0.450033 0.357359 0.027 Uiso 1 1 calc R . . . .
C42 C 0.5916(2) -0.1707(4) 0.45755(13) 0.0231(9) Uani 1 1 d . . . . .
H42A H 0.588670 -0.086801 0.440092 0.035 Uiso 1 1 calc GR . . . .
H42B H 0.540161 -0.196973 0.463234 0.035 Uiso 1 1 calc GR . . . .
H42C H 0.613887 -0.246246 0.442592 0.035 Uiso 1 1 calc GR . . . .
C14 C 0.8868(2) 0.2528(4) 0.46035(13) 0.0184(8) Uani 1 1 d . . . . .
C22 C 0.8623(3) 0.6945(5) 0.14693(15) 0.0318(10) Uani 1 1 d . . . . .
H22 H 0.835036 0.636716 0.126262 0.038 Uiso 1 1 calc R . . . .
C8 C 0.6873(2) 1.3341(5) 0.21154(14) 0.0253(9) Uani 1 1 d . . . . .
C11 C 0.5151(2) 0.3975(5) 0.41773(14) 0.0248(9) Uani 1 1 d . . . . .
C12 C 0.5160(2) 0.2887(5) 0.38779(14) 0.0256(9) Uani 1 1 d . . . . .
H12 H 0.475103 0.282507 0.365620 0.031 Uiso 1 1 calc R . . . .
C5 C 0.8612(2) 0.8782(4) 0.20072(13) 0.0234(8) Uani 1 1 d . . . . .
C16 C 0.9438(2) 0.4285(4) 0.41584(13) 0.0218(8) Uani 1 1 d . . . . .
C28 C 0.6450(3) 0.8475(5) 0.26179(13) 0.0259(9) Uani 1 1 d . . . . .
C19 C 0.9433(3) 0.8749(5) 0.20720(15) 0.0307(10) Uani 1 1 d . . . . .
C29 C 0.6971(2) 0.3133(4) 0.49376(13) 0.0220(8) Uani 1 1 d . . . . .
H29A H 0.713287 0.220471 0.503639 0.033 Uiso 1 1 calc GR . . . .
H29B H 0.676527 0.363581 0.516554 0.033 Uiso 1 1 calc GR . . . .
H29C H 0.740944 0.363824 0.485322 0.033 Uiso 1 1 calc GR . . . .
C43 C 0.6061(2) -0.0171(4) 0.52278(15) 0.0272(9) Uani 1 1 d . . . . .
H43A H 0.638450 0.005677 0.548995 0.041 Uiso 1 1 calc GR . . . .
H43B H 0.555147 -0.043562 0.529260 0.041 Uiso 1 1 calc GR . . . .
H43C H 0.601945 0.063836 0.504098 0.041 Uiso 1 1 calc GR . . . .
C6 C 0.7251(2) 0.8693(4) 0.26976(12) 0.0215(8) Uani 1 1 d . . . . .
C47 C 0.8665(2) 1.2565(5) 0.15958(14) 0.0281(10) Uani 1 1 d . . . . .
H47A H 0.866354 1.334509 0.179237 0.042 Uiso 1 1 calc GR . . . .
H47B H 0.897221 1.280411 0.137041 0.042 Uiso 1 1 calc GR . . . .
H47C H 0.888254 1.174640 0.174750 0.042 Uiso 1 1 calc GR . . . .
C15 C 0.9428(2) 0.3569(4) 0.45423(13) 0.0212(8) Uani 1 1 d . . . . .
H15 H 0.980642 0.378311 0.477036 0.025 Uiso 1 1 calc R . . . .
C3 C 0.6425(2) -0.1419(4) 0.50017(13) 0.0207(8) Uani 1 1 d . . . . .
C40 C 0.5914(2) 0.9221(5) 0.22742(15) 0.0318(10) Uani 1 1 d . . . . .
H40A H 0.555143 0.979487 0.240691 0.048 Uiso 1 1 calc GR . . . .
H40B H 0.563377 0.853303 0.209007 0.048 Uiso 1 1 calc GR . . . .
H40C H 0.621476 0.981106 0.210669 0.048 Uiso 1 1 calc GR . . . .
C33 C 1.0062(2) 0.5335(5) 0.40875(15) 0.0283(9) Uani 1 1 d . . . . .
H33A H 1.042550 0.490701 0.391790 0.042 Uiso 1 1 calc GR . . . .
H33B H 1.032906 0.562324 0.436053 0.042 Uiso 1 1 calc GR . . . .
H33C H 0.982892 0.614712 0.393869 0.042 Uiso 1 1 calc GR . . . .
C18 C 0.8280(2) 0.2962(4) 0.38727(13) 0.0207(8) Uani 1 1 d . . . . .
C9 C 0.6349(2) 0.3005(4) 0.45564(13) 0.0193(8) Uani 1 1 d . . . . .
C25 C 0.7309(3) 0.6900(4) 0.32539(13) 0.0259(9) Uani 1 1 d . . . . .
H25 H 0.760177 0.636050 0.346349 0.031 Uiso 1 1 calc R . . . .
C7 C 0.7828(2) 1.2244(4) 0.14000(13) 0.0217(8) Uani 1 1 d . . . . .
C26 C 0.6513(3) 0.6697(5) 0.31842(13) 0.0274(9) Uani 1 1 d . . . . .
C37 C 0.7333(3) 0.7798(5) 0.16298(14) 0.0299(10) Uani 1 1 d . . . . .
H37A H 0.717968 0.729252 0.136691 0.045 Uiso 1 1 calc GR . . . .
H37B H 0.712857 0.874306 0.160524 0.045 Uiso 1 1 calc GR . . . .
H37C H 0.713309 0.732215 0.186436 0.045 Uiso 1 1 calc GR . . . .
C4 C 0.8044(2) -0.2464(4) 0.48145(14) 0.0227(9) Uani 1 1 d . . . . .
C49 C 0.7497(3) 1.3507(5) 0.11291(14) 0.0319(10) Uani 1 1 d . . . . .
H49A H 0.697012 1.330715 0.101084 0.048 Uiso 1 1 calc GR . . . .
H49B H 0.780743 1.366932 0.089918 0.048 Uiso 1 1 calc GR . . . .
H49C H 0.750696 1.433440 0.130773 0.048 Uiso 1 1 calc GR . . . .
C13 C 0.5757(2) 0.1884(4) 0.38968(13) 0.0227(9) Uani 1 1 d . . . . .
C2 C 0.8291(2) 0.2207(4) 0.42639(12) 0.0182(8) Uani 1 1 d . . . . .
C23 C 0.8208(3) 0.7856(5) 0.17124(14) 0.0276(9) Uani 1 1 d . . . . .
C48 C 0.7844(3) 1.0985(5) 0.10895(13) 0.0263(9) Uani 1 1 d . . . . .
H48A H 0.806152 1.017395 0.124506 0.040 Uiso 1 1 calc GR . . . .
H48B H 0.815796 1.122239 0.086660 0.040 Uiso 1 1 calc GR . . . .
H48C H 0.732338 1.077436 0.096288 0.040 Uiso 1 1 calc GR . . . .
C27 C 0.6097(3) 0.7481(5) 0.28603(14) 0.0279(10) Uani 1 1 d . . . . .
H27 H 0.556290 0.733881 0.280235 0.033 Uiso 1 1 calc R . . . .
C41 C 0.6418(3) -0.2711(5) 0.52933(14) 0.0275(9) Uani 1 1 d . . . . .
H41A H 0.659175 -0.352522 0.514808 0.041 Uiso 1 1 calc GR . . . .
H41B H 0.589854 -0.287015 0.536128 0.041 Uiso 1 1 calc GR . . . .
H41C H 0.676002 -0.255020 0.555427 0.041 Uiso 1 1 calc GR . . . .
C32 C 0.8928(2) 0.1842(5) 0.50411(12) 0.0245(9) Uani 1 1 d . . . . .
H32A H 0.940342 0.131044 0.509004 0.037 Uiso 1 1 calc GR . . . .
H32B H 0.849265 0.121844 0.505367 0.037 Uiso 1 1 calc GR . . . .
H32C H 0.892518 0.255894 0.525833 0.037 Uiso 1 1 calc GR . . . .
C44 C 0.8801(2) -0.1894(5) 0.46615(15) 0.0299(10) Uani 1 1 d . . . . .
H44A H 0.867490 -0.135493 0.440214 0.045 Uiso 1 1 calc GR . . . .
H44B H 0.913117 -0.267236 0.460620 0.045 Uiso 1 1 calc GR . . . .
H44C H 0.906636 -0.129894 0.488087 0.045 Uiso 1 1 calc GR . . . .
C31 C 0.5728(3) 0.0771(5) 0.35484(14) 0.0306(10) Uani 1 1 d . . . . .
H31A H 0.619755 0.081151 0.341323 0.046 Uiso 1 1 calc GR . . . .
H31B H 0.528754 0.094201 0.333714 0.046 Uiso 1 1 calc GR . . . .
H31C H 0.568111 -0.014873 0.367330 0.046 Uiso 1 1 calc GR . . . .
C45 C 0.8302(3) -0.3360(5) 0.52209(14) 0.0290(10) Uani 1 1 d . . . . .
H45A H 0.860274 -0.278249 0.543233 0.044 Uiso 1 1 calc GR . . . .
H45B H 0.861389 -0.414128 0.514547 0.044 Uiso 1 1 calc GR . . . .
H45C H 0.785055 -0.371162 0.533714 0.044 Uiso 1 1 calc GR . . . .
C50 C 0.7555(3) 1.4280(5) 0.22840(15) 0.0303(10) Uani 1 1 d . . . . .
H50A H 0.795247 1.371599 0.244326 0.046 Uiso 1 1 calc GR . . . .
H50B H 0.738145 1.499345 0.246902 0.046 Uiso 1 1 calc GR . . . .
H50C H 0.776236 1.472361 0.204621 0.046 Uiso 1 1 calc GR . . . .
C10 C 0.5746(2) 0.3999(4) 0.45164(13) 0.0214(8) Uani 1 1 d . . . . .
H10 H 0.574369 0.470088 0.472468 0.026 Uiso 1 1 calc R . . . .
C51 C 0.6469(2) 1.2785(5) 0.24944(14) 0.0300(10) Uani 1 1 d . . . . .
H51A H 0.601099 1.226428 0.238548 0.045 Uiso 1 1 calc GR . . . .
H51B H 0.632587 1.356845 0.266373 0.045 Uiso 1 1 calc GR . . . .
H51C H 0.681996 1.217575 0.267061 0.045 Uiso 1 1 calc GR . . . .
C30 C 0.4529(3) 0.5096(5) 0.41284(17) 0.0349(11) Uani 1 1 d . . . . .
H30A H 0.470699 0.589179 0.397657 0.052 Uiso 1 1 calc GR . . . .
H30B H 0.441717 0.539296 0.440807 0.052 Uiso 1 1 calc GR . . . .
H30C H 0.406489 0.471789 0.396944 0.052 Uiso 1 1 calc GR . . . .
C39 C 0.6105(3) 0.5655(5) 0.34495(16) 0.0370(11) Uani 1 1 d . . . . .
H39A H 0.600281 0.479488 0.328949 0.056 Uiso 1 1 calc GR . . . .
H39B H 0.562256 0.605626 0.351407 0.056 Uiso 1 1 calc GR . . . .
H39C H 0.643184 0.545554 0.371311 0.056 Uiso 1 1 calc GR . . . .
C24 C 0.7690(3) 0.7884(5) 0.30217(13) 0.0255(9) Uani 1 1 d . . . . .
C52 C 0.6252(3) 1.4243(5) 0.18385(16) 0.0375(12) Uani 1 1 d . . . . .
H52A H 0.648291 1.467488 0.160657 0.056 Uiso 1 1 calc GR . . . .
H52B H 0.606172 1.496528 0.201449 0.056 Uiso 1 1 calc GR . . . .
H52C H 0.582835 1.364646 0.172302 0.056 Uiso 1 1 calc GR . . . .
C20 C 0.9819(3) 0.7775(5) 0.18336(16) 0.0364(12) Uani 1 1 d . . . . .
H20 H 1.035951 0.772443 0.188237 0.044 Uiso 1 1 calc R . . . .
C34 C 0.7683(2) 0.2690(5) 0.34890(13) 0.0262(9) Uani 1 1 d . . . . .
H34A H 0.774296 0.337555 0.326874 0.039 Uiso 1 1 calc GR . . . .
H34B H 0.716971 0.276600 0.357450 0.039 Uiso 1 1 calc GR . . . .
H34C H 0.775584 0.175689 0.337949 0.039 Uiso 1 1 calc GR . . . .
C46 C 0.7631(3) -0.3422(4) 0.44612(14) 0.0257(9) Uani 1 1 d . . . . .
H46A H 0.718659 -0.385687 0.456390 0.039 Uiso 1 1 calc GR . . . .
H46B H 0.798399 -0.414215 0.438849 0.039 Uiso 1 1 calc GR . . . .
H46C H 0.746301 -0.286473 0.421031 0.039 Uiso 1 1 calc GR . . . .
C35 C 0.9918(3) 0.9713(6) 0.23837(16) 0.0380(12) Uani 1 1 d . . . . .
H35A H 0.981160 1.068130 0.230404 0.057 Uiso 1 1 calc GR . . . .
H35B H 1.046030 0.951708 0.237528 0.057 Uiso 1 1 calc GR . . . .
H35C H 0.978862 0.955324 0.266990 0.057 Uiso 1 1 calc GR . . . .
C36 C 0.9862(3) 0.5879(5) 0.1266(2) 0.0518(16) Uani 1 1 d . . . . .
H36A H 1.005005 0.508928 0.144218 0.078 Uiso 1 1 calc GR . . . .
H36B H 1.029373 0.636265 0.116624 0.078 Uiso 1 1 calc GR . . . .
H36C H 0.951635 0.554508 0.102376 0.078 Uiso 1 1 calc GR . . . .
C21 C 0.9428(3) 0.6886(5) 0.15289(17) 0.0377(12) Uani 1 1 d . . . . .
C38 C 0.8557(3) 0.8022(5) 0.31279(16) 0.0366(11) Uani 1 1 d . . . . .
H38A H 0.880828 0.769427 0.288891 0.055 Uiso 1 1 calc GR . . . .
H38B H 0.872795 0.746359 0.337800 0.055 Uiso 1 1 calc GR . . . .
H38C H 0.868918 0.899636 0.318468 0.055 Uiso 1 1 calc GR . . . .


_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 P1 2.6723(10) . ?
Bi1 C1 2.275(4) . ?
Bi1 C2 2.299(4) . ?
Bi2 P2 2.6841(10) . ?
Bi2 C5 2.278(4) . ?
Bi2 C6 2.314(4) . ?
P1 C3 1.903(4) . ?
P1 C4 1.903(4) . ?
P2 C8 1.912(4) . ?
P2 C7 1.904(4) . ?
C1 C9 1.410(6) . ?
C1 C13 1.407(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.393(6) . ?
C17 C18 1.393(6) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C42 C3 1.531(5) . ?
C14 C15 1.409(5) . ?
C14 C2 1.400(5) . ?
C14 C32 1.506(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.402(6) . ?
C22 C21 1.383(7) . ?
C8 C50 1.519(6) . ?
C8 C51 1.539(6) . ?
C8 C52 1.550(6) . ?
C11 C12 1.391(6) . ?
C11 C10 1.385(6) . ?
C11 C30 1.505(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.399(6) . ?
C5 C19 1.410(6) . ?
C5 C23 1.396(6) . ?
C16 C15 1.380(6) . ?
C16 C33 1.501(6) . ?
C28 C6 1.393(6) . ?
C28 C40 1.507(6) . ?
C28 C27 1.393(6) . ?
C19 C20 1.403(7) . ?
C19 C35 1.511(7) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C29 C9 1.511(5) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C43 C3 1.547(5) . ?
C6 C24 1.415(6) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C47 C7 1.532(6) . ?
C15 H15 0.9300 . ?
C3 C41 1.525(6) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C18 C2 1.414(5) . ?
C18 C34 1.508(5) . ?
C9 C10 1.398(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(6) . ?
C25 C24 1.393(6) . ?
C7 C49 1.534(6) . ?
C7 C48 1.537(6) . ?
C26 C27 1.384(6) . ?
C26 C39 1.515(6) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C37 C23 1.505(6) . ?
C4 C44 1.543(6) . ?
C4 C45 1.547(6) . ?
C4 C46 1.536(6) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C13 C31 1.511(6) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C27 H27 0.9300 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C10 H10 0.9300 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C24 C38 1.501(6) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.384(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36 C21 1.514(7) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
C1 Bi1 P1 102.77(10) . . ?
C1 Bi1 C2 93.71(14) . . ?
C2 Bi1 P1 107.63(10) . . ?
C5 Bi2 P2 100.73(10) . . ?
C5 Bi2 C6 94.88(14) . . ?
C6 Bi2 P2 107.62(10) . . ?
C3 P1 Bi1 101.68(13) . . ?
C3 P1 C4 108.62(18) . . ?
C4 P1 Bi1 95.95(13) . . ?
C8 P2 Bi2 97.23(13) . . ?
C7 P2 Bi2 101.58(13) . . ?
C7 P2 C8 109.43(19) . . ?
C9 C1 Bi1 123.5(3) . . ?
C13 C1 Bi1 116.8(3) . . ?
C13 C1 C9 119.4(4) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C18 C17 C16 122.0(4) . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C3 C42 H42A 109.5 . . ?
C3 C42 H42B 109.5 . . ?
C3 C42 H42C 109.5 . . ?
C15 C14 C32 116.8(3) . . ?
C2 C14 C15 119.1(4) . . ?
C2 C14 C32 124.1(3) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.6(5) . . ?
C50 C8 P2 117.0(3) . . ?
C50 C8 C51 109.7(4) . . ?
C50 C8 C52 109.2(4) . . ?
C51 C8 P2 106.8(3) . . ?
C51 C8 C52 105.7(4) . . ?
C52 C8 P2 107.8(3) . . ?
C12 C11 C30 121.1(4) . . ?
C10 C11 C12 117.4(4) . . ?
C10 C11 C30 121.5(4) . . ?
C11 C12 H12 118.7 . . ?
C11 C12 C13 122.7(4) . . ?
C13 C12 H12 118.7 . . ?
C19 C5 Bi2 117.0(3) . . ?
C23 C5 Bi2 123.2(3) . . ?
C23 C5 C19 119.7(4) . . ?
C17 C16 C33 120.2(4) . . ?
C15 C16 C17 117.3(4) . . ?
C15 C16 C33 122.5(4) . . ?
C6 C28 C40 124.8(4) . . ?
C6 C28 C27 119.6(4) . . ?
C27 C28 C40 115.6(4) . . ?
C5 C19 C35 123.3(4) . . ?
C20 C19 C5 118.2(5) . . ?
C20 C19 C35 118.4(4) . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C9 C29 H29A 109.5 . . ?
C9 C29 H29B 109.5 . . ?
C9 C29 H29C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C3 C43 H43A 109.5 . . ?
C3 C43 H43B 109.5 . . ?
C3 C43 H43C 109.5 . . ?
C28 C6 Bi2 129.0(3) . . ?
C28 C6 C24 119.0(4) . . ?
C24 C6 Bi2 111.8(3) . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C7 C47 H47A 109.5 . . ?
C7 C47 H47B 109.5 . . ?
C7 C47 H47C 109.5 . . ?
C14 C15 H15 118.6 . . ?
C16 C15 C14 122.8(4) . . ?
C16 C15 H15 118.6 . . ?
C42 C3 P1 117.8(3) . . ?
C42 C3 C43 108.0(3) . . ?
C43 C3 P1 104.7(3) . . ?
C41 C3 P1 108.7(3) . . ?
C41 C3 C42 109.5(3) . . ?
C41 C3 C43 107.7(3) . . ?
C28 C40 H40A 109.5 . . ?
C28 C40 H40B 109.5 . . ?
C28 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C16 C33 H33A 109.5 . . ?
C16 C33 H33B 109.5 . . ?
C16 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C17 C18 C2 120.0(4) . . ?
C17 C18 C34 117.4(4) . . ?
C2 C18 C34 122.6(4) . . ?
C1 C9 C29 122.7(4) . . ?
C10 C9 C1 119.3(4) . . ?
C10 C9 C29 118.0(4) . . ?
C26 C25 H25 118.8 . . ?
C26 C25 C24 122.4(4) . . ?
C24 C25 H25 118.8 . . ?
C47 C7 P2 117.8(3) . . ?
C47 C7 C49 109.8(3) . . ?
C47 C7 C48 108.5(3) . . ?
C49 C7 P2 108.3(3) . . ?
C49 C7 C48 106.7(3) . . ?
C48 C7 P2 105.2(3) . . ?
C25 C26 C27 117.4(4) . . ?
C25 C26 C39 121.7(4) . . ?
C27 C26 C39 120.9(4) . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C23 C37 H37A 109.5 . . ?
C23 C37 H37B 109.5 . . ?
C23 C37 H37C 109.5 . . ?
C44 C4 P1 106.8(3) . . ?
C44 C4 C45 106.0(3) . . ?
C45 C4 P1 108.7(3) . . ?
C46 C4 P1 116.7(3) . . ?
C46 C4 C44 108.7(4) . . ?
C46 C4 C45 109.4(3) . . ?
C7 C49 H49A 109.5 . . ?
C7 C49 H49B 109.5 . . ?
C7 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C1 C13 C31 122.4(4) . . ?
C12 C13 C1 118.8(4) . . ?
C12 C13 C31 118.8(4) . . ?
C14 C2 Bi1 129.2(3) . . ?
C14 C2 C18 118.7(4) . . ?
C18 C2 Bi1 111.8(3) . . ?
C22 C23 C37 117.0(4) . . ?
C5 C23 C22 119.7(4) . . ?
C5 C23 C37 123.3(4) . . ?
C7 C48 H48A 109.5 . . ?
C7 C48 H48B 109.5 . . ?
C7 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C28 C27 H27 118.8 . . ?
C26 C27 C28 122.4(4) . . ?
C26 C27 H27 118.8 . . ?
C3 C41 H41A 109.5 . . ?
C3 C41 H41B 109.5 . . ?
C3 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C14 C32 H32A 109.5 . . ?
C14 C32 H32B 109.5 . . ?
C14 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C4 C44 H44A 109.5 . . ?
C4 C44 H44B 109.5 . . ?
C4 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C13 C31 H31A 109.5 . . ?
C13 C31 H31B 109.5 . . ?
C13 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C4 C45 H45A 109.5 . . ?
C4 C45 H45B 109.5 . . ?
C4 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C8 C50 H50A 109.5 . . ?
C8 C50 H50B 109.5 . . ?
C8 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C11 C10 C9 122.3(4) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C8 C51 H51A 109.5 . . ?
C8 C51 H51B 109.5 . . ?
C8 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C11 C30 H30A 109.5 . . ?
C11 C30 H30B 109.5 . . ?
C11 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C26 C39 H39A 109.5 . . ?
C26 C39 H39B 109.5 . . ?
C26 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C6 C24 C38 123.1(4) . . ?
C25 C24 C6 119.2(4) . . ?
C25 C24 C38 117.7(4) . . ?
C8 C52 H52A 109.5 . . ?
C8 C52 H52B 109.5 . . ?
C8 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C19 C20 H20 118.6 . . ?
C21 C20 C19 122.7(4) . . ?
C21 C20 H20 118.6 . . ?
C18 C34 H34A 109.5 . . ?
C18 C34 H34B 109.5 . . ?
C18 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C4 C46 H46A 109.5 . . ?
C4 C46 H46B 109.5 . . ?
C4 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C19 C35 H35A 109.5 . . ?
C19 C35 H35B 109.5 . . ?
C19 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C21 C36 H36A 109.5 . . ?
C21 C36 H36B 109.5 . . ?
C21 C36 H36C 109.5 . . ?
C22 C21 C20 117.9(4) . . ?
C22 C21 C36 120.6(5) . . ?
C20 C21 C36 121.5(5) . . ?
C24 C38 H38A 109.5 . . ?
C24 C38 H38B 109.5 . . ?
C24 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
