# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_13712sadabs
_database_code_depnum_ccdc_archive 'CCDC 2063973'
loop_
_audit_author_name
_audit_author_address
'Nils Noethling'
;Max Planck Institut fuer Kohlenforschung
Germany
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;

_audit_block_code                KUJ-KA-258-01
_audit_creation_date             2021-02-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
4,6-bis(diphenylbismuthanyl)dibenzo[b,d]furan
;
_chemical_formula_moiety         'C36 H26 Bi2 O'
_chemical_formula_sum            'C36 H26 Bi2 O'
_chemical_formula_weight         892.53
_chemical_absolute_configuration ad
_chemical_properties_physical    none
_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'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1284(3)
_cell_length_b                   13.2853(8)
_cell_length_c                   34.731(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2827.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    48642


_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.9997
_cell_measurement_theta_min      2.8
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.457
_exptl_absorpt_correction_T_max  0.77837
_exptl_absorpt_correction_T_min  0.17161

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  dichloromethane, hexane'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0250
0.00 0.00 1.00 0.0250
-1.00 0.00 0.00 0.0800
1.00 0.00 0.00 0.0800
0.00 1.00 0.00 0.0100
0.00 -1.00 0.00 0.0100
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            38138
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.802

_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7693
_reflns_number_total             8618
_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       'EVALCCD V. 1.6, 2008'

_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'EVALCCD V. 1.6, 2008'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_refine_diff_density_max         1.247
_refine_diff_density_min         -1.882
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details 
;
 Flack x determined using 3069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.044(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         8618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+3.6970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0604

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.1765 and 0.7789 (SADABS).

INTENSITY STATISTICS FOR DATASET 	
#------------------------------------------------------------------------------- 
Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 2.60     174    182     95.6     5.57    133.10   41.53  0.0417  0.0194
 2.60 - 1.73     420    420    100.0     6.09    106.45   41.07  0.0370  0.0200
 1.73 - 1.37     587    587    100.0     6.00     68.90   34.90  0.0386  0.0220
 1.37 - 1.19     584    584    100.0     5.73     51.66   31.40  0.0430  0.0249
 1.19 - 1.08     610    610    100.0     5.29     42.94   26.93  0.0453  0.0286
 1.08 - 1.00     599    599    100.0     4.91     35.62   22.89  0.0499  0.0332
 1.00 - 0.95     502    502    100.0     4.69     29.04   20.79  0.0540  0.0382
 0.95 - 0.90     604    604    100.0     4.41     28.21   19.38  0.0561  0.0419
 0.90 - 0.86     587    587    100.0     4.14     19.86   15.36  0.0672  0.0529
 0.86 - 0.83     553    553    100.0     4.08     20.22   15.00  0.0737  0.0550
 0.83 - 0.80     595    595    100.0     3.82     15.55   12.04  0.0853  0.0690
 0.80 - 0.77     672    672    100.0     3.65     15.49   11.15  0.0899  0.0736
 0.77 - 0.75     564    564    100.0     3.56     12.98    9.92  0.1066  0.0866
 0.75 - 0.73     589    589    100.0     3.37     12.18    8.91  0.1102  0.0960
 0.73 - 0.71     671    673     99.7     3.21     10.65    7.79  0.1377  0.1149
 0.71 - 0.69     715    718     99.6     3.09      9.17    6.50  0.1570  0.1393
 0.69 - 0.68     398    400     99.5     3.02      8.15    5.77  0.1671  0.1620
 0.68 - 0.66     901    905     99.6     2.96      7.78    5.24  0.1880  0.1790
 0.66 - 0.65     489    494     99.0     2.84      6.96    4.47  0.2065  0.2190
 0.65 - 0.64     516    522     98.9     2.70      5.69    3.45  0.2487  0.2950
 0.64 - 0.63     262    276     94.9     2.55      5.92    3.29  0.2413  0.3034
#-------------------------------------------------------------------------------
 0.73 - 0.63    3952   3988     99.1     2.95      8.06    5.50  0.1763  0.1757
  Inf - 0.63   11592  11636     99.6     4.02     26.44   15.54  0.0575  0.0498
#-------------------------------------------------------------------------------

A resolution cut off (SHEL 99 0.7) was applied to suppress poorly measured
intensities at higher diffraction angles. 

 Highest peak    1.25  at  0.6632  0.4361  0.1516  [  0.82 A from BI1 ]
 Deepest hole   -1.88  at  0.0542  0.8208  0.0995  [  0.79 A from BI2 ]
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36)
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

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 0.97122(4) 0.56346(2) 0.65157(2) 0.01946(6) Uani 1 1 d . . . . .
Bi2 Bi 0.50902(4) 0.23094(2) 0.60007(2) 0.01768(6) Uani 1 1 d . . . . .
O1 O 0.5556(7) 0.4007(3) 0.66820(13) 0.0183(9) Uani 1 1 d . . . . .
C1 C 0.5590(11) 0.4752(5) 0.6966(2) 0.0198(13) Uani 1 1 d . . . . .
C2 C 0.7111(11) 0.5511(5) 0.6975(2) 0.0221(14) Uani 1 1 d . . . . .
C3 C 0.6927(12) 0.6174(5) 0.7282(2) 0.0228(15) Uani 1 1 d . . . . .
H3 H 0.796670 0.669983 0.730932 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5237(13) 0.6085(5) 0.75522(19) 0.0244(14) Uani 1 1 d . . . . .
H4 H 0.514857 0.655525 0.775778 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3683(12) 0.5320(5) 0.7525(2) 0.0241(15) Uani 1 1 d . . . . .
H5 H 0.252936 0.526938 0.770695 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3873(12) 0.4632(5) 0.7224(2) 0.0203(14) Uani 1 1 d . . . . .
C7 C 0.2641(11) 0.3764(5) 0.7089(2) 0.0181(13) Uani 1 1 d . . . . .
C8 C 0.0704(12) 0.3277(5) 0.7197(2) 0.0218(14) Uani 1 1 d . . . . .
H8 H -0.010133 0.348807 0.741636 0.026 Uiso 1 1 calc R U . . .
C9 C 0.0007(12) 0.2473(5) 0.69716(18) 0.0232(13) Uani 1 1 d . . . . .
H9 H -0.129541 0.213049 0.704108 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1146(11) 0.2154(5) 0.6649(2) 0.0215(14) Uani 1 1 d . . . . .
H10 H 0.061456 0.159543 0.650679 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3074(10) 0.2638(5) 0.6528(2) 0.0193(13) Uani 1 1 d . . . . .
C12 C 0.3724(11) 0.3428(5) 0.67605(19) 0.0173(13) Uani 1 1 d . . . . .
C13 C 1.0480(10) 0.7246(5) 0.66549(19) 0.0187(12) Uani 1 1 d . . . . .
C14 C 0.8983(11) 0.8024(6) 0.6597(2) 0.0237(15) Uani 1 1 d . . . . .
H14 H 0.757812 0.787722 0.649608 0.028 Uiso 1 1 calc R U . . .
C15 C 0.9532(13) 0.9014(5) 0.6687(2) 0.0251(15) Uani 1 1 d . . . . .
H15 H 0.850459 0.953985 0.664768 0.030 Uiso 1 1 calc R U . . .
C16 C 1.1598(12) 0.9231(6) 0.6835(2) 0.0267(16) Uani 1 1 d . . . . .
H16 H 1.198308 0.990545 0.689590 0.032 Uiso 1 1 calc R U . . .
C17 C 1.3089(12) 0.8457(6) 0.6893(2) 0.0275(17) Uani 1 1 d . . . . .
H17 H 1.448819 0.859969 0.699748 0.033 Uiso 1 1 calc R U . . .
C18 C 1.2531(11) 0.7480(6) 0.6800(2) 0.0244(15) Uani 1 1 d . . . . .
H18 H 1.357125 0.695797 0.683462 0.029 Uiso 1 1 calc R U . . .
C19 C 0.7436(10) 0.6036(5) 0.6030(2) 0.0201(13) Uani 1 1 d . . . . .
C20 C 0.5331(10) 0.5656(5) 0.59920(19) 0.0233(13) Uani 1 1 d . . . . .
H20 H 0.468055 0.530611 0.620123 0.028 Uiso 1 1 calc R U . . .
C21 C 0.4167(11) 0.5782(5) 0.5651(2) 0.0251(15) Uani 1 1 d . . . . .
H21 H 0.273575 0.551239 0.562953 0.030 Uiso 1 1 calc R U . . .
C22 C 0.5062(15) 0.6288(5) 0.5348(2) 0.0294(15) Uani 1 1 d . . . . .
H22 H 0.425648 0.637230 0.511665 0.035 Uiso 1 1 calc R U . . .
C23 C 0.7147(15) 0.6679(6) 0.5379(3) 0.036(2) Uani 1 1 d . . . . .
H23 H 0.777269 0.703290 0.516852 0.043 Uiso 1 1 calc R U . . .
C24 C 0.8330(13) 0.6555(6) 0.5718(3) 0.0288(17) Uani 1 1 d . . . . .
H24 H 0.975930 0.682679 0.573749 0.035 Uiso 1 1 calc R U . . .
C25 C 0.3747(10) 0.0761(5) 0.59020(19) 0.0181(13) Uani 1 1 d . . . . .
C26 C 0.5193(12) -0.0043(5) 0.59539(18) 0.0243(13) Uani 1 1 d . . . . .
H26 H 0.661774 0.007931 0.605088 0.029 Uiso 1 1 calc R U . . .
C27 C 0.4564(14) -0.1013(6) 0.5865(2) 0.0331(18) Uani 1 1 d . . . . .
H27 H 0.556302 -0.155217 0.589873 0.040 Uiso 1 1 calc R U . . .
C28 C 0.2507(14) -0.1202(6) 0.5729(3) 0.0325(19) Uani 1 1 d . . . . .
H28 H 0.209067 -0.187146 0.566764 0.039 Uiso 1 1 calc R U . . .
C29 C 0.1033(13) -0.0423(6) 0.5681(2) 0.0303(17) Uani 1 1 d . . . . .
H29 H -0.039785 -0.055670 0.558934 0.036 Uiso 1 1 calc R U . . .
C30 C 0.1667(11) 0.0566(6) 0.5770(2) 0.0237(14) Uani 1 1 d . . . . .
H30 H 0.065970 0.110352 0.573896 0.028 Uiso 1 1 calc R U . . .
C31 C 0.2797(11) 0.3112(5) 0.55996(19) 0.0167(13) Uani 1 1 d . . . . .
C32 C 0.3504(11) 0.3321(5) 0.5228(2) 0.0200(14) Uani 1 1 d . . . . .
H32 H 0.489339 0.309079 0.514404 0.024 Uiso 1 1 calc R U . . .
C33 C 0.2179(12) 0.3869(5) 0.4976(2) 0.0221(14) Uani 1 1 d . . . . .
H33 H 0.267843 0.401263 0.472326 0.026 Uiso 1 1 calc R U . . .
C34 C 0.0147(12) 0.4205(4) 0.50922(19) 0.0220(13) Uani 1 1 d . . . . .
H34 H -0.075112 0.457625 0.492031 0.026 Uiso 1 1 calc R U . . .
C35 C -0.0566(11) 0.3992(5) 0.5464(2) 0.0219(14) Uani 1 1 d . . . . .
H35 H -0.195609 0.422318 0.554696 0.026 Uiso 1 1 calc R U . . .
C36 C 0.0745(11) 0.3444(5) 0.5716(2) 0.0222(14) Uani 1 1 d . . . . .
H36 H 0.023749 0.329605 0.596861 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C2 2.262(7) . ?
Bi1 C13 2.244(6) . ?
Bi1 C19 2.253(7) . ?
Bi2 C11 2.252(7) . ?
Bi2 C25 2.243(7) . ?
Bi2 C31 2.248(7) . ?
O1 C1 1.397(8) . ?
O1 C12 1.387(8) . ?
C1 C2 1.374(9) . ?
C1 C6 1.392(10) . ?
C2 C3 1.387(10) . ?
C3 H3 0.9500 . ?
C3 C4 1.403(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(10) . ?
C6 C7 1.456(9) . ?
C7 C8 1.403(9) . ?
C7 C12 1.392(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(10) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.410(9) . ?
C11 C12 1.383(9) . ?
C13 C14 1.397(9) . ?
C13 C18 1.389(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(10) . ?
C15 H15 0.9500 . ?
C15 C16 1.397(10) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(9) . ?
C19 C24 1.396(11) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.365(10) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(12) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.400(9) . ?
C25 C30 1.378(9) . ?
C26 H26 0.9500 . ?
C26 C27 1.379(10) . ?
C27 H27 0.9500 . ?
C27 C28 1.369(12) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(11) . ?
C29 H29 0.9500 . ?
C29 C30 1.405(10) . ?
C30 H30 0.9500 . ?
C31 C32 1.391(10) . ?
C31 C36 1.393(9) . ?
C32 H32 0.9500 . ?
C32 C33 1.397(10) . ?
C33 H33 0.9500 . ?
C33 C34 1.382(9) . ?
C34 H34 0.9500 . ?
C34 C35 1.393(9) . ?
C35 H35 0.9500 . ?
C35 C36 1.394(10) . ?
C36 H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 Bi1 C2 93.7(2) . . ?
C13 Bi1 C19 93.8(2) . . ?
C19 Bi1 C2 96.3(3) . . ?
C25 Bi2 C11 95.8(2) . . ?
C25 Bi2 C31 96.4(2) . . ?
C31 Bi2 C11 94.0(2) . . ?
C12 O1 C1 105.4(5) . . ?
C2 C1 O1 123.2(6) . . ?
C2 C1 C6 125.6(6) . . ?
C6 C1 O1 111.2(6) . . ?
C1 C2 Bi1 121.0(5) . . ?
C1 C2 C3 115.4(7) . . ?
C3 C2 Bi1 123.6(5) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(7) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(6) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 118.1(7) . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 118.1(7) . . ?
C1 C6 C7 106.0(6) . . ?
C5 C6 C7 135.9(7) . . ?
C8 C7 C6 135.8(7) . . ?
C12 C7 C6 105.7(6) . . ?
C12 C7 C8 118.4(6) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 C7 117.5(7) . . ?
C9 C8 H8 121.2 . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.3(7) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.6(7) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 Bi2 127.9(5) . . ?
C12 C11 Bi2 117.6(5) . . ?
C12 C11 C10 114.4(7) . . ?
O1 C12 C7 111.7(6) . . ?
C11 C12 O1 122.6(6) . . ?
C11 C12 C7 125.7(6) . . ?
C14 C13 Bi1 122.5(5) . . ?
C18 C13 Bi1 118.8(5) . . ?
C18 C13 C14 118.7(6) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.5(6) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(7) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(7) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.9(7) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.3(7) . . ?
C17 C18 H18 119.3 . . ?
C20 C19 Bi1 124.0(5) . . ?
C20 C19 C24 118.0(7) . . ?
C24 C19 Bi1 117.1(5) . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.8(7) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(7) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.8(7) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.1(8) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.7(7) . . ?
C23 C24 H24 119.7 . . ?
C26 C25 Bi2 116.6(5) . . ?
C30 C25 Bi2 124.2(5) . . ?
C30 C25 C26 119.0(7) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(7) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.4(7) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.4(7) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.3 . . ?
C28 C29 C30 119.5(7) . . ?
C30 C29 H29 120.3 . . ?
C25 C30 C29 120.3(7) . . ?
C25 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C32 C31 Bi2 118.4(5) . . ?
C32 C31 C36 119.2(6) . . ?
C36 C31 Bi2 122.3(5) . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.2(6) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 119.7 . . ?
C34 C33 C32 120.7(7) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 120.4 . . ?
C33 C34 C35 119.1(6) . . ?
C35 C34 H34 120.4 . . ?
C34 C35 H35 119.7 . . ?
C34 C35 C36 120.5(6) . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 120.2(7) . . ?
C31 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C2 C3 C4 177.8(5) . . . . ?
Bi1 C13 C14 C15 -179.9(5) . . . . ?
Bi1 C13 C18 C17 -179.4(6) . . . . ?
Bi1 C19 C20 C21 -167.8(5) . . . . ?
Bi1 C19 C24 C23 168.8(6) . . . . ?
Bi2 C11 C12 O1 -0.6(8) . . . . ?
Bi2 C11 C12 C7 177.6(5) . . . . ?
Bi2 C25 C26 C27 -174.0(5) . . . . ?
Bi2 C25 C30 C29 173.9(6) . . . . ?
Bi2 C31 C32 C33 -176.3(5) . . . . ?
Bi2 C31 C36 C35 176.0(5) . . . . ?
O1 C1 C2 Bi1 1.1(9) . . . . ?
O1 C1 C2 C3 -178.7(6) . . . . ?
O1 C1 C6 C5 180.0(6) . . . . ?
O1 C1 C6 C7 -1.4(7) . . . . ?
C1 O1 C12 C7 -1.7(7) . . . . ?
C1 O1 C12 C11 176.7(6) . . . . ?
C1 C2 C3 C4 -2.4(10) . . . . ?
C1 C6 C7 C8 -175.5(8) . . . . ?
C1 C6 C7 C12 0.3(7) . . . . ?
C2 C1 C6 C5 -1.6(11) . . . . ?
C2 C1 C6 C7 177.1(7) . . . . ?
C2 C3 C4 C5 0.6(11) . . . . ?
C3 C4 C5 C6 1.0(10) . . . . ?
C4 C5 C6 C1 -0.5(10) . . . . ?
C4 C5 C6 C7 -178.7(7) . . . . ?
C5 C6 C7 C8 2.8(15) . . . . ?
C5 C6 C7 C12 178.6(8) . . . . ?
C6 C1 C2 Bi1 -177.2(5) . . . . ?
C6 C1 C2 C3 3.0(10) . . . . ?
C6 C7 C8 C9 176.5(7) . . . . ?
C6 C7 C12 O1 0.9(7) . . . . ?
C6 C7 C12 C11 -177.4(6) . . . . ?
C7 C8 C9 C10 -0.4(10) . . . . ?
C8 C7 C12 O1 177.6(6) . . . . ?
C8 C7 C12 C11 -0.7(11) . . . . ?
C8 C9 C10 C11 -0.9(10) . . . . ?
C9 C10 C11 Bi2 -176.5(5) . . . . ?
C9 C10 C11 C12 1.2(10) . . . . ?
C10 C11 C12 O1 -178.6(6) . . . . ?
C10 C11 C12 C7 -0.5(10) . . . . ?
C12 O1 C1 C2 -176.6(6) . . . . ?
C12 O1 C1 C6 1.9(7) . . . . ?
C12 C7 C8 C9 1.1(10) . . . . ?
C13 C14 C15 C16 0.1(11) . . . . ?
C14 C13 C18 C17 1.3(11) . . . . ?
C14 C15 C16 C17 -0.3(11) . . . . ?
C15 C16 C17 C18 0.9(12) . . . . ?
C16 C17 C18 C13 -1.4(12) . . . . ?
C18 C13 C14 C15 -0.6(11) . . . . ?
C19 C20 C21 C22 -0.5(11) . . . . ?
C20 C19 C24 C23 -0.5(11) . . . . ?
C20 C21 C22 C23 0.1(11) . . . . ?
C21 C22 C23 C24 0.1(12) . . . . ?
C22 C23 C24 C19 0.1(13) . . . . ?
C24 C19 C20 C21 0.7(10) . . . . ?
C25 C26 C27 C28 -0.7(11) . . . . ?
C26 C25 C30 C29 -1.4(11) . . . . ?
C26 C27 C28 C29 -0.4(13) . . . . ?
C27 C28 C29 C30 0.6(12) . . . . ?
C28 C29 C30 C25 0.3(12) . . . . ?
C30 C25 C26 C27 1.6(10) . . . . ?
C31 C32 C33 C34 -0.4(10) . . . . ?
C32 C31 C36 C35 -0.9(10) . . . . ?
C32 C33 C34 C35 0.2(10) . . . . ?
C33 C34 C35 C36 -0.3(10) . . . . ?
C34 C35 C36 C31 0.7(10) . . . . ?
C36 C31 C32 C33 0.8(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_shelx_SHELXL_version_number     2018/3
####################################################################### 
# 
# 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_13680sadabs
_database_code_depnum_ccdc_archive 'CCDC 2063977'
loop_
_audit_author_name
_audit_author_address
'Nils Noethling'
;Max Planck Institut fuer Kohlenforschung
Germany
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_block_code                KUJ-KA-319-01
_audit_creation_date             2021-01-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
4,6-bis(dichlorodiphenyl-l5-bismuthanyl)dibenzo[b,d]furan
;
_chemical_formula_moiety         'C36 H26 Bi2 Cl4 O'
_chemical_formula_sum            'C36 H26 Bi2 Cl4 O'
_chemical_formula_weight         1034.33
_chemical_properties_physical    Moisture-sensitive,Moisture-sensitive
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.0281(4)
_cell_length_b                   12.1880(5)
_cell_length_c                   15.1195(6)
_cell_angle_alpha                101.289(2)
_cell_angle_beta                 90.246(2)
_cell_angle_gamma                95.156(2)
_cell_volume                     1624.47(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9042


_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.8857
_cell_measurement_theta_min      2.2656
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.544
_exptl_absorpt_coefficient_mu    11.176
_exptl_absorpt_correction_T_max  0.89794
_exptl_absorpt_correction_T_min  0.62769

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  dichloromethane, pentane'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0050
0.00 -1.00 0.00 0.0050
0.00 0.00 1.00 0.0150
0.00 0.00 -1.00 0.0150
1.00 0.00 0.00 0.0300
-1.00 0.00 0.00 0.0150
_exptl_crystal_size_max          0.062
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            65647
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.077
_diffrn_reflns_theta_min         1.374

_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         1\mS
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11437
_reflns_number_total             14207
_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       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'APEX3 (Bruker AXS, 2005-2017)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_refine_diff_density_max         1.959
_refine_diff_density_min         -1.375
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         14207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.046
_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)+(0.0225P)²+0.4014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0527
_refine_ls_wR_factor_ref         0.0566

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.5748 and 0.9627 (SADABS).
INTENSITY STATISTICS FOR DATASET 	
#------------------------------------------------------------------------------- 
Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 2.62     193    193    100.0    16.66    105.31  100.95  0.0218  0.0077
 2.62 - 1.73     465    465    100.0    18.07     77.19   95.92  0.0213  0.0078
 1.73 - 1.36     659    659    100.0    18.21     56.68   85.70  0.0239  0.0084
 1.36 - 1.19     637    637    100.0    17.89     40.21   73.92  0.0290  0.0095
 1.19 - 1.08     644    644    100.0    16.19     34.66   63.67  0.0328  0.0110
 1.08 - 1.00     659    659    100.0    12.04     30.16   50.59  0.0367  0.0144
 1.00 - 0.94     643    643    100.0     9.96     24.96   41.52  0.0403  0.0173
 0.94 - 0.89     700    700    100.0     8.42     22.48   34.84  0.0441  0.0206
 0.89 - 0.85     654    654    100.0     7.81     18.60   29.75  0.0501  0.0243
 0.85 - 0.82     606    606    100.0     7.49     18.04   27.34  0.0527  0.0262
 0.82 - 0.79     676    676    100.0     7.22     14.37   23.26  0.0635  0.0317
 0.79 - 0.77     526    526    100.0     6.93     14.23   21.71  0.0608  0.0330
 0.77 - 0.74     882    882    100.0     6.73     13.25   19.76  0.0695  0.0367
 0.74 - 0.72     680    680    100.0     6.25     12.03   17.70  0.0789  0.0427
 0.72 - 0.71     354    354    100.0     6.39     12.06   17.95  0.0819  0.0426
 0.71 - 0.69     773    773    100.0     6.05      9.64   14.48  0.0936  0.0526
 0.69 - 0.67     914    914    100.0     5.83      9.13   13.50  0.1011  0.0579
 0.67 - 0.66     488    488    100.0     5.68      8.11   11.88  0.1123  0.0651
 0.66 - 0.65     509    509    100.0     5.49      7.47   11.07  0.1194  0.0728
 0.65 - 0.64     555    555    100.0     5.38      8.04   11.27  0.1236  0.0705
 0.64 - 0.63     601    601    100.0     5.13      7.03    9.96  0.1317  0.0819
#-------------------------------------------------------------------------------
 0.73 - 0.63    4559   4559    100.0     5.74      8.91   13.13  0.1027  0.0599
  Inf - 0.63   12818  12818    100.0     9.20     22.61   34.27  0.0359  0.0217
#-------------------------------------------------------------------------------

 Highest peak    1.96  at  0.1551  0.2742  0.2311  [  0.68 A from BI1 ]
 Deepest hole   -1.38  at  0.5271  0.7200  0.3086  [  0.60 A from BI2 ]
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36)
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

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 0.08380(2) 0.27795(2) 0.21731(2) 0.01452(2) Uani 1 1 d . . . . .
Bi2 Bi 0.47207(2) 0.74102(2) 0.32301(2) 0.01533(2) Uani 1 1 d . . . . .
Cl1 Cl 0.25225(7) 0.12772(5) 0.24622(4) 0.02231(12) Uani 1 1 d . . . . .
Cl2 Cl -0.07976(7) 0.43405(5) 0.19479(4) 0.02215(12) Uani 1 1 d . . . . .
Cl3 Cl 0.55119(8) 0.55343(5) 0.23961(4) 0.02584(14) Uani 1 1 d . . . . .
Cl4 Cl 0.36585(8) 0.92385(6) 0.40099(5) 0.03218(16) Uani 1 1 d . . . . .
O1 O 0.25485(19) 0.50534(14) 0.37376(10) 0.0168(3) Uani 1 1 d . . . . .
C1 C 0.1702(3) 0.4260(2) 0.41048(15) 0.0166(5) Uani 1 1 d . . . . .
C2 C 0.0837(3) 0.3344(2) 0.36357(15) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.0011(3) 0.2653(2) 0.41251(17) 0.0242(6) Uani 1 1 d . . . . .
H3 H -0.060837 0.202169 0.381692 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0093(3) 0.2889(2) 0.50680(18) 0.0274(6) Uani 1 1 d . . . . .
H4 H -0.049218 0.242257 0.539340 0.033 Uiso 1 1 calc R U . . .
C5 C 0.1004(3) 0.3782(2) 0.55341(17) 0.0238(6) Uani 1 1 d . . . . .
H5 H 0.107384 0.392040 0.617415 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1822(3) 0.4481(2) 0.50498(16) 0.0185(5) Uani 1 1 d . . . . .
C7 C 0.2860(3) 0.5467(2) 0.52830(16) 0.0195(5) Uani 1 1 d . . . . .
C8 C 0.3466(3) 0.6106(2) 0.60945(17) 0.0263(6) Uani 1 1 d . . . . .
H8 H 0.321810 0.590251 0.665449 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4431(4) 0.7037(3) 0.60618(18) 0.0336(7) Uani 1 1 d . . . . .
H9 H 0.487628 0.746358 0.660690 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4773(3) 0.7372(3) 0.52511(17) 0.0299(7) Uani 1 1 d . . . . .
H10 H 0.541915 0.803110 0.525056 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4166(3) 0.6739(2) 0.44388(16) 0.0210(5) Uani 1 1 d . . . . .
C12 C 0.3246(3) 0.5781(2) 0.44688(16) 0.0188(5) Uani 1 1 d . . . . .
C13 C 0.2430(3) 0.32368(19) 0.11666(15) 0.0179(5) Uani 1 1 d . . . . .
C14 C 0.3899(3) 0.3039(2) 0.12252(18) 0.0250(6) Uani 1 1 d . . . . .
H14 H 0.426412 0.275766 0.171905 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4831(3) 0.3261(3) 0.0546(2) 0.0319(7) Uani 1 1 d . . . . .
H15 H 0.585245 0.313585 0.057408 0.038 Uiso 1 1 calc R U . . .
C16 C 0.4294(4) 0.3663(2) -0.01707(18) 0.0286(6) Uani 1 1 d . . . . .
H16 H 0.494151 0.379800 -0.063920 0.034 Uiso 1 1 calc R U . . .
C17 C 0.2833(4) 0.3868(2) -0.02123(17) 0.0276(6) Uani 1 1 d . . . . .
H17 H 0.247435 0.415362 -0.070602 0.033 Uiso 1 1 calc R U . . .
C18 C 0.1867(3) 0.3662(2) 0.04645(16) 0.0219(5) Uani 1 1 d . . . . .
H18 H 0.085328 0.380924 0.044448 0.026 Uiso 1 1 calc R U . . .
C19 C -0.0968(3) 0.1451(2) 0.16635(16) 0.0169(5) Uani 1 1 d . . . . .
C20 C -0.0589(3) 0.0420(2) 0.1227(2) 0.0284(6) Uani 1 1 d . . . . .
H20 H 0.042707 0.027960 0.115965 0.034 Uiso 1 1 calc R U . . .
C21 C -0.1708(3) -0.0415(2) 0.0885(2) 0.0313(7) Uani 1 1 d . . . . .
H21 H -0.145646 -0.112517 0.057062 0.038 Uiso 1 1 calc R U . . .
C22 C -0.3166(3) -0.0221(2) 0.0998(2) 0.0288(6) Uani 1 1 d . . . . .
H22 H -0.392602 -0.080001 0.077218 0.035 Uiso 1 1 calc R U . . .
C23 C -0.3539(3) 0.0817(3) 0.1441(2) 0.0369(8) Uani 1 1 d . . . . .
H23 H -0.455642 0.094957 0.151780 0.044 Uiso 1 1 calc R U . . .
C24 C -0.2437(3) 0.1667(2) 0.1773(2) 0.0294(6) Uani 1 1 d . . . . .
H24 H -0.268870 0.238518 0.207096 0.035 Uiso 1 1 calc R U . . .
C25 C 0.6985(3) 0.8252(2) 0.32914(16) 0.0192(5) Uani 1 1 d . . . . .
C26 C 0.7312(3) 0.9221(2) 0.39264(19) 0.0240(5) Uani 1 1 d . . . . .
H26 H 0.656546 0.953593 0.431152 0.029 Uiso 1 1 calc R U . . .
C27 C 0.8755(3) 0.9725(2) 0.3990(2) 0.0306(7) Uani 1 1 d . . . . .
H27 H 0.901325 1.037452 0.444180 0.037 Uiso 1 1 calc R U . . .
C28 C 0.9818(3) 0.9299(3) 0.3409(2) 0.0361(7) Uani 1 1 d . . . . .
H28 H 1.079255 0.967165 0.344359 0.043 Uiso 1 1 calc R U . . .
C29 C 0.9474(3) 0.8330(3) 0.2774(2) 0.0371(8) Uani 1 1 d . . . . .
H29 H 1.021688 0.803559 0.237701 0.045 Uiso 1 1 calc R U . . .
C30 C 0.8056(3) 0.7784(3) 0.27105(18) 0.0267(6) Uani 1 1 d . . . . .
H30 H 0.781786 0.710732 0.228252 0.032 Uiso 1 1 calc R U . . .
C31 C 0.3282(3) 0.74532(19) 0.20664(15) 0.0156(4) Uani 1 1 d . . . . .
C32 C 0.3353(3) 0.8458(2) 0.17677(17) 0.0191(5) Uani 1 1 d . . . . .
H32 H 0.393234 0.910509 0.208730 0.023 Uiso 1 1 calc R U . . .
C33 C 0.2559(3) 0.8498(2) 0.09896(17) 0.0218(5) Uani 1 1 d . . . . .
H33 H 0.262302 0.917015 0.075653 0.026 Uiso 1 1 calc R U . . .
C34 C 0.1679(3) 0.7571(2) 0.05550(17) 0.0255(6) Uani 1 1 d . . . . .
H34 H 0.113106 0.760553 0.002484 0.031 Uiso 1 1 calc R U . . .
C35 C 0.1586(4) 0.6589(2) 0.08837(19) 0.0296(6) Uani 1 1 d . . . . .
H35 H 0.095668 0.595839 0.058340 0.035 Uiso 1 1 calc R U . . .
C36 C 0.2399(3) 0.6506(2) 0.16473(17) 0.0248(6) Uani 1 1 d . . . . .
H36 H 0.234992 0.582867 0.187152 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl1 2.5816(6) . ?
Bi1 Cl2 2.5827(6) . ?
Bi1 C2 2.184(2) . ?
Bi1 C13 2.213(2) . ?
Bi1 C19 2.213(2) . ?
Bi2 Cl3 2.5496(6) . ?
Bi2 Cl4 2.5769(6) . ?
Bi2 C11 2.186(3) . ?
Bi2 C25 2.197(3) . ?
Bi2 C31 2.194(2) . ?
O1 C1 1.381(3) . ?
O1 C12 1.384(3) . ?
C1 C2 1.375(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.395(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(4) . ?
C6 C7 1.441(4) . ?
C7 C8 1.398(4) . ?
C7 C12 1.396(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(4) . ?
C11 C12 1.379(4) . ?
C13 C14 1.375(4) . ?
C13 C18 1.383(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.368(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(4) . ?
C19 C24 1.380(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.364(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(4) . ?
C25 C30 1.393(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.371(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.383(3) . ?
C31 C36 1.383(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.387(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.372(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.379(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.390(4) . ?
C36 H36 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
Cl1 Bi1 Cl2 177.46(2) . . ?
C2 Bi1 Cl1 86.64(7) . . ?
C2 Bi1 Cl2 91.17(7) . . ?
C2 Bi1 C13 130.24(9) . . ?
C2 Bi1 C19 113.08(9) . . ?
C13 Bi1 Cl1 89.26(7) . . ?
C13 Bi1 Cl2 91.19(7) . . ?
C19 Bi1 Cl1 90.29(7) . . ?
C19 Bi1 Cl2 91.75(7) . . ?
C19 Bi1 C13 116.51(8) . . ?
Cl3 Bi2 Cl4 174.32(2) . . ?
C11 Bi2 Cl3 92.41(7) . . ?
C11 Bi2 Cl4 87.53(7) . . ?
C11 Bi2 C25 112.86(9) . . ?
C11 Bi2 C31 128.63(9) . . ?
C25 Bi2 Cl3 93.52(7) . . ?
C25 Bi2 Cl4 91.74(7) . . ?
C31 Bi2 Cl3 88.73(6) . . ?
C31 Bi2 Cl4 86.88(6) . . ?
C31 Bi2 C25 118.32(9) . . ?
C1 O1 C12 104.98(18) . . ?
O1 C1 C6 111.9(2) . . ?
C2 C1 O1 126.3(2) . . ?
C2 C1 C6 121.7(2) . . ?
C1 C2 Bi1 124.53(17) . . ?
C1 C2 C3 118.3(2) . . ?
C3 C2 Bi1 116.85(18) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.7(2) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 105.3(2) . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 135.0(2) . . ?
C8 C7 C6 134.4(2) . . ?
C12 C7 C6 105.9(2) . . ?
C12 C7 C8 119.7(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.4(2) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 Bi2 115.9(2) . . ?
C12 C11 Bi2 126.00(18) . . ?
C12 C11 C10 118.1(2) . . ?
O1 C12 C7 111.9(2) . . ?
C11 C12 O1 126.2(2) . . ?
C11 C12 C7 121.9(2) . . ?
C14 C13 Bi1 120.16(19) . . ?
C14 C13 C18 122.4(2) . . ?
C18 C13 Bi1 117.36(19) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.2(3) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 118.0(3) . . ?
C13 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
C20 C19 Bi1 118.46(19) . . ?
C20 C19 C24 121.2(2) . . ?
C24 C19 Bi1 120.36(18) . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.3(3) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 118.8(3) . . ?
C19 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C26 C25 Bi2 118.36(19) . . ?
C26 C25 C30 121.9(3) . . ?
C30 C25 Bi2 119.72(19) . . ?
C25 C26 H26 120.9 . . ?
C25 C26 C27 118.3(3) . . ?
C27 C26 H26 120.9 . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 120.9(3) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.1(3) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 H30 120.9 . . ?
C29 C30 C25 118.2(3) . . ?
C29 C30 H30 120.9 . . ?
C32 C31 Bi2 116.25(17) . . ?
C32 C31 C36 122.8(2) . . ?
C36 C31 Bi2 120.90(18) . . ?
C31 C32 H32 120.9 . . ?
C31 C32 C33 118.3(2) . . ?
C33 C32 H32 120.9 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.2(2) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 119.8 . . ?
C33 C34 C35 120.3(3) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 119.5 . . ?
C34 C35 C36 121.1(3) . . ?
C36 C35 H35 119.5 . . ?
C31 C36 C35 117.1(2) . . ?
C31 C36 H36 121.4 . . ?
C35 C36 H36 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C2 C3 C4 172.6(2) . . . . ?
Bi1 C13 C14 C15 175.3(2) . . . . ?
Bi1 C13 C18 C17 -174.93(18) . . . . ?
Bi1 C19 C20 C21 -178.6(2) . . . . ?
Bi1 C19 C24 C23 179.6(2) . . . . ?
Bi2 C11 C12 O1 2.2(4) . . . . ?
Bi2 C11 C12 C7 -174.7(2) . . . . ?
Bi2 C25 C26 C27 177.3(2) . . . . ?
Bi2 C25 C30 C29 -179.3(2) . . . . ?
Bi2 C31 C32 C33 174.73(18) . . . . ?
Bi2 C31 C36 C35 -176.4(2) . . . . ?
O1 C1 C2 Bi1 9.3(4) . . . . ?
O1 C1 C2 C3 -177.6(2) . . . . ?
O1 C1 C6 C5 178.1(2) . . . . ?
O1 C1 C6 C7 -1.9(3) . . . . ?
C1 O1 C12 C7 -0.1(3) . . . . ?
C1 O1 C12 C11 -177.2(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C6 C7 C8 -179.3(3) . . . . ?
C1 C6 C7 C12 1.8(3) . . . . ?
C2 C1 C6 C5 -2.5(4) . . . . ?
C2 C1 C6 C7 177.6(2) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C3 C4 C5 C6 2.0(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C5 C6 C7 C12 -178.2(3) . . . . ?
C6 C1 C2 Bi1 -170.10(19) . . . . ?
C6 C1 C2 C3 3.0(4) . . . . ?
C6 C7 C8 C9 -178.6(3) . . . . ?
C6 C7 C12 O1 -1.1(3) . . . . ?
C6 C7 C12 C11 176.2(2) . . . . ?
C7 C8 C9 C10 2.1(5) . . . . ?
C8 C7 C12 O1 179.8(2) . . . . ?
C8 C7 C12 C11 -2.9(4) . . . . ?
C8 C9 C10 C11 -1.9(5) . . . . ?
C9 C10 C11 Bi2 177.3(2) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 O1 180.0(3) . . . . ?
C10 C11 C12 C7 3.1(4) . . . . ?
C12 O1 C1 C2 -178.2(3) . . . . ?
C12 O1 C1 C6 1.3(3) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C13 C18 C17 1.5(4) . . . . ?
C14 C15 C16 C17 1.3(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C18 C13 C14 C15 -1.0(4) . . . . ?
C19 C20 C21 C22 -1.4(5) . . . . ?
C20 C19 C24 C23 0.6(5) . . . . ?
C20 C21 C22 C23 1.2(5) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C22 C23 C24 C19 -0.8(5) . . . . ?
C24 C19 C20 C21 0.5(4) . . . . ?
C25 C26 C27 C28 2.8(4) . . . . ?
C26 C25 C30 C29 -1.1(4) . . . . ?
C26 C27 C28 C29 -2.7(5) . . . . ?
C27 C28 C29 C30 0.6(5) . . . . ?
C28 C29 C30 C25 1.3(5) . . . . ?
C30 C25 C26 C27 -0.9(4) . . . . ?
C31 C32 C33 C34 2.6(4) . . . . ?
C32 C31 C36 C35 1.4(4) . . . . ?
C32 C33 C34 C35 -0.5(4) . . . . ?
C33 C34 C35 C36 -1.3(5) . . . . ?
C34 C35 C36 C31 0.9(4) . . . . ?
C36 C31 C32 C33 -3.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_shelx_SHELXL_version_number     2018/3
####################################################################### 
# 
# 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_13708sadabs
_database_code_depnum_ccdc_archive 'CCDC 2063974'
loop_
_audit_author_name
_audit_author_address
'Nils Noethling'
;Max Planck Institut fuer Kohlenforschung
Germany
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;

_audit_block_code                KUJ-KA-317-01
_audit_creation_date             2021-02-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
4,6-bis(dichlorodiphenyl-λ⁵-bismuthanyl)-10,11-dihydrodibenzo[b,f]oxepine
;
_chemical_formula_moiety         'C38 H30 Bi2 Cl4 O, C6 H6'
_chemical_formula_sum            'C44 H36 Bi2 Cl4 O'
_chemical_formula_weight         1140.49
_chemical_properties_physical    none
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.0198(3)
_cell_length_b                   12.1771(7)
_cell_length_c                   15.7796(11)
_cell_angle_alpha                96.190(5)
_cell_angle_beta                 103.900(4)
_cell_angle_gamma                114.199(3)
_cell_volume                     1988.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    118897


_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.9999
_cell_measurement_theta_min      2.7121
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.139
_exptl_absorpt_correction_T_max  0.59321
_exptl_absorpt_correction_T_min  0.30255

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_exptl_crystal_description       prism
_exptl_crystal_F_000             1084
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  benzene, pentane'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -2.00 -1.00 0.0650
-1.00 2.00 1.00 0.0650
0.00 -1.00 1.00 0.0400
0.00 1.00 -1.00 0.0400
-1.00 0.00 0.00 0.0350
1.00 0.00 0.00 0.0350
1.00 -1.00 -2.00 0.0750
-1.00 1.00 2.00 0.0750
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            75349
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.716

_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10803
_reflns_number_total             12134
_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       'EVALCCD V. 1.6, 2008'

_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'EVALCCD V. 1.6, 2008'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         1.030
_refine_diff_density_min         -1.794
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         12134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0210
_refine_ls_restrained_S_all      1.072
_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)+(0.0102P)²+2.5079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0436
_refine_ls_wR_factor_ref         0.0457

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.3089 and 0.5885 (SADABS).

INTENSITY STATISTICS FOR DATASET 	
#------------------------------------------------------------------------------- 
Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 2.32     326    335     97.3     7.26    132.92   52.70  0.0448  0.0163
 2.32 - 1.56     763    763    100.0     7.62     95.60   47.40  0.0342  0.0166
 1.56 - 1.24    1082   1082    100.0     7.50     62.64   39.99  0.0341  0.0181
 1.24 - 1.08    1130   1130    100.0     7.27     47.51   36.25  0.0368  0.0201
 1.08 - 0.98    1126   1126    100.0     6.89     36.41   30.62  0.0417  0.0228
 0.98 - 0.91    1098   1098    100.0     6.47     28.86   27.10  0.0457  0.0263
 0.91 - 0.86    1011   1011    100.0     6.15     24.12   23.50  0.0506  0.0300
 0.86 - 0.81    1279   1279    100.0     5.80     20.66   20.40  0.0557  0.0344
 0.81 - 0.78     947    947    100.0     5.52     18.15   18.56  0.0619  0.0389
 0.78 - 0.75    1091   1091    100.0     5.28     15.08   15.78  0.0735  0.0454
 0.75 - 0.72    1289   1289    100.0     5.05     14.01   14.83  0.0794  0.0509
 0.72 - 0.70     992    992    100.0     4.84     11.26   12.27  0.0925  0.0623
 0.70 - 0.68    1115   1115    100.0     4.61     10.57   11.32  0.1002  0.0688
 0.68 - 0.66    1225   1225    100.0     4.48      8.63    9.44  0.1237  0.0863
 0.66 - 0.64    1423   1423    100.0     4.21      7.55    7.95  0.1461  0.1079
 0.64 - 0.63     729    729    100.0     4.15      7.54    7.43  0.1543  0.1176
 0.63 - 0.62     842    842    100.0     4.01      7.00    6.68  0.1665  0.1369
 0.62 - 0.60    1796   1796    100.0     3.86      5.60    4.96  0.2054  0.1933
 0.60 - 0.59    1020   1020    100.0     3.68      4.73    3.67  0.2448  0.2715
 0.59 - 0.58    1426   1474     96.7     3.44      4.54    3.11  0.2664  0.3321
#-------------------------------------------------------------------------------
 0.68 - 0.58    8461   8509     99.4     3.95      6.39    6.03  0.1755  0.1652
  Inf - 0.58   21710  21767     99.7     5.24     22.57   17.57  0.0540  0.0416
#-------------------------------------------------------------------------------
A resolution cut off (SHEL 0.7 55) was applied to suppress poorly measured 
intensities at higher diffraction angles.

 Highest peak    1.10  at  0.3811  0.7911  0.1186  [  0.69 A from BI2 ]
 Deepest hole   -1.76  at  0.3409  0.6926  0.1480  [  0.60 A from BI2 ]
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35),
 C36(H36), C37(H37), C38(H38), C51(H51), C52(H52), C53(H53), C61(H61), C62(H62),
  C63(H63)
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

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 0.32233(2) 0.24070(2) 0.57263(2) 0.01407(2) Uani 1 1 d . . . . .
Bi2 Bi 0.64570(2) 0.26252(2) 0.86719(2) 0.01979(3) Uani 1 1 d . . . . .
Cl1 Cl 0.20785(6) 0.00068(5) 0.54154(4) 0.02089(11) Uani 1 1 d . . . . .
Cl2 Cl 0.40005(6) 0.47813(5) 0.60044(4) 0.02065(11) Uani 1 1 d . . . . .
Cl3 Cl 0.43027(6) 0.19088(6) 0.90190(5) 0.02676(13) Uani 1 1 d . . . . .
Cl4 Cl 0.86957(7) 0.33729(9) 0.84559(6) 0.03926(18) Uani 1 1 d . . . . .
O1 O 0.44173(16) 0.36366(17) 0.77328(12) 0.0200(4) Uani 1 1 d . . . . .
C1 C 0.3132(2) 0.3315(2) 0.75875(17) 0.0196(5) Uani 1 1 d . . . . .
C2 C 0.2331(2) 0.2483(2) 0.67759(17) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.1004(2) 0.1932(2) 0.65519(19) 0.0224(5) Uani 1 1 d . . . . .
H3 H 0.047572 0.135921 0.599306 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0471(3) 0.2245(3) 0.7173(2) 0.0289(6) Uani 1 1 d . . . . .
H4 H -0.043082 0.183940 0.706469 0.035 Uiso 1 1 calc R U . . .
C5 C 0.1264(3) 0.3151(3) 0.7947(2) 0.0298(6) Uani 1 1 d . . . . .
H5 H 0.088248 0.339357 0.834508 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2597(3) 0.3724(3) 0.81715(18) 0.0254(5) Uani 1 1 d . . . . .
C7 C 0.3395(3) 0.4861(3) 0.89239(19) 0.0330(7) Uani 1 1 d . . . . .
H7A H 0.390359 0.466759 0.942478 0.040 Uiso 1 1 calc R U . . .
H7B H 0.282683 0.513351 0.914917 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4304(3) 0.5906(3) 0.8593(2) 0.0314(6) Uani 1 1 d . . . . .
H8A H 0.387433 0.586531 0.796257 0.038 Uiso 1 1 calc R U . . .
H8B H 0.451994 0.671884 0.896348 0.038 Uiso 1 1 calc R U . . .
C9 C 0.5507(3) 0.5777(3) 0.86570(17) 0.0232(5) Uani 1 1 d . . . . .
C10 C 0.6710(3) 0.6753(3) 0.91416(19) 0.0289(6) Uani 1 1 d . . . . .
H10 H 0.676002 0.753751 0.935543 0.035 Uiso 1 1 calc R U . . .
C11 C 0.7825(3) 0.6628(3) 0.93223(19) 0.0295(6) Uani 1 1 d . . . . .
H11 H 0.863280 0.732940 0.960661 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7755(2) 0.5469(3) 0.90856(18) 0.0253(5) Uani 1 1 d . . . . .
H12 H 0.850680 0.535247 0.924235 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6570(2) 0.4479(2) 0.86152(16) 0.0198(5) Uani 1 1 d . . . . .
C14 C 0.5462(2) 0.4633(2) 0.83463(16) 0.0191(5) Uani 1 1 d . . . . .
C15 C 0.2179(2) 0.2251(2) 0.43316(16) 0.0166(4) Uani 1 1 d . . . . .
C16 C 0.0905(2) 0.1386(2) 0.39284(18) 0.0238(5) Uani 1 1 d . . . . .
H16 H 0.043888 0.086042 0.425392 0.029 Uiso 1 1 calc R U . . .
C17 C 0.0329(3) 0.1314(3) 0.3033(2) 0.0311(6) Uani 1 1 d . . . . .
H17 H -0.054680 0.073896 0.274251 0.037 Uiso 1 1 calc R U . . .
C18 C 0.1024(3) 0.2074(3) 0.25602(19) 0.0292(6) Uani 1 1 d . . . . .
H18 H 0.062560 0.200808 0.194645 0.035 Uiso 1 1 calc R U . . .
C19 C 0.2294(3) 0.2929(2) 0.29780(19) 0.0261(6) Uani 1 1 d . . . . .
H19 H 0.276349 0.344842 0.265102 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2885(3) 0.3028(2) 0.38740(17) 0.0209(5) Uani 1 1 d . . . . .
H20 H 0.375529 0.361674 0.416714 0.025 Uiso 1 1 calc R U . . .
C21 C 0.5176(2) 0.2588(2) 0.58912(17) 0.0187(5) Uani 1 1 d . . . . .
C22 C 0.6182(3) 0.3760(3) 0.6133(3) 0.0478(10) Uani 1 1 d . . . . .
H22 H 0.604765 0.446625 0.627111 0.057 Uiso 1 1 calc R U . . .
C23 C 0.7400(3) 0.3892(3) 0.6171(3) 0.0550(12) Uani 1 1 d . . . . .
H23 H 0.810534 0.469535 0.633639 0.066 Uiso 1 1 calc R U . . .
C24 C 0.7587(3) 0.2867(3) 0.5972(2) 0.0336(7) Uani 1 1 d . . . . .
H24 H 0.841693 0.296167 0.598680 0.040 Uiso 1 1 calc R U . . .
C25 C 0.6573(3) 0.1705(3) 0.5750(2) 0.0366(7) Uani 1 1 d . . . . .
H25 H 0.671204 0.099864 0.563071 0.044 Uiso 1 1 calc R U . . .
C26 C 0.5341(3) 0.1549(3) 0.5698(2) 0.0298(6) Uani 1 1 d . . . . .
H26 H 0.463559 0.074597 0.553420 0.036 Uiso 1 1 calc R U . . .
C27 C 0.5726(3) 0.0809(3) 0.77403(19) 0.0334(7) Uani 1 1 d . . . . .
C28 C 0.4434(3) 0.0119(3) 0.72891(19) 0.0326(7) Uani 1 1 d . . . . .
H28 H 0.384023 0.043201 0.733569 0.039 Uiso 1 1 calc R U . . .
C29 C 0.4023(4) -0.1054(3) 0.6762(2) 0.0457(9) Uani 1 1 d . . . . .
H29 H 0.313963 -0.154431 0.643188 0.055 Uiso 1 1 calc R U . . .
C30 C 0.4899(5) -0.1509(4) 0.6717(3) 0.0636(14) Uani 1 1 d . . . . .
H30 H 0.461021 -0.231584 0.636639 0.076 Uiso 1 1 calc R U . . .
C31 C 0.6184(5) -0.0796(5) 0.7177(3) 0.0738(16) Uani 1 1 d . . . . .
H31 H 0.677628 -0.111392 0.713990 0.089 Uiso 1 1 calc R U . . .
C32 C 0.6626(4) 0.0386(4) 0.7697(2) 0.0541(11) Uani 1 1 d . . . . .
H32 H 0.751316 0.088548 0.801150 0.065 Uiso 1 1 calc R U . . .
C33 C 0.7342(3) 0.2575(3) 1.00557(18) 0.0235(5) Uani 1 1 d . . . . .
C34 C 0.6695(3) 0.1562(3) 1.0362(2) 0.0357(7) Uani 1 1 d . . . . .
H34 H 0.591788 0.089535 0.997518 0.043 Uiso 1 1 calc R U . . .
C35 C 0.7186(4) 0.1520(3) 1.1241(2) 0.0453(9) Uani 1 1 d . . . . .
H35 H 0.675203 0.081625 1.145641 0.054 Uiso 1 1 calc R U . . .
C36 C 0.8309(4) 0.2503(4) 1.1806(2) 0.0419(8) Uani 1 1 d . . . . .
H36 H 0.863058 0.248104 1.241234 0.050 Uiso 1 1 calc R U . . .
C37 C 0.8967(3) 0.3515(3) 1.1492(2) 0.0374(7) Uani 1 1 d . . . . .
H37 H 0.974073 0.418370 1.188097 0.045 Uiso 1 1 calc R U . . .
C38 C 0.8491(3) 0.3552(3) 1.0604(2) 0.0298(6) Uani 1 1 d . . . . .
H38 H 0.894627 0.423418 1.037761 0.036 Uiso 1 1 calc R U . . .
C51 C 0.0679(3) 0.4370(3) 0.5296(3) 0.0448(9) Uani 1 1 d . . . . .
H51 H 0.115066 0.393589 0.550303 0.054 Uiso 1 1 calc R U . . .
C52 C 0.0983(4) 0.5514(4) 0.5799(3) 0.0498(9) Uani 1 1 d . . . . .
H52 H 0.166368 0.586747 0.635166 0.060 Uiso 1 1 calc R U . . .
C53 C 0.0298(4) 0.6136(3) 0.5498(3) 0.0468(9) Uani 1 1 d . . . . .
H53 H 0.050447 0.692245 0.584282 0.056 Uiso 1 1 calc R U . . .
C61 C 0.0257(3) 0.9586(3) 0.0769(2) 0.0420(8) Uani 1 1 d . . . . .
H61 H 0.043434 0.930196 0.129895 0.050 Uiso 1 1 calc R U . . .
C62 C 0.1059(3) 0.9788(3) 0.0251(2) 0.0409(8) Uani 1 1 d . . . . .
H62 H 0.178984 0.964030 0.042480 0.049 Uiso 1 1 calc R U . . .
C63 C 0.0813(3) 1.0203(3) -0.0517(2) 0.0414(8) Uani 1 1 d . . . . .
H63 H 0.137174 1.034420 -0.087225 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl1 2.5972(6) . ?
Bi1 Cl2 2.5962(6) . ?
Bi1 C2 2.192(2) . ?
Bi1 C15 2.200(2) . ?
Bi1 C21 2.212(2) . ?
Bi2 Cl3 2.5881(7) . ?
Bi2 Cl4 2.5856(7) . ?
Bi2 C13 2.218(3) . ?
Bi2 C27 2.216(3) . ?
Bi2 C33 2.206(3) . ?
O1 C1 1.381(3) . ?
O1 C14 1.379(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.400(3) . ?
C2 C3 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(4) . ?
C6 C7 1.502(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.537(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.499(4) . ?
C9 C10 1.397(4) . ?
C9 C14 1.401(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 C14 1.392(3) . ?
C15 C16 1.388(3) . ?
C15 C20 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(4) . ?
C21 C26 1.373(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.375(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.373(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.393(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(5) . ?
C27 C32 1.387(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.395(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.376(7) . ?
C31 H31 0.9500 . ?
C31 C32 1.391(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.372(4) . ?
C33 C38 1.389(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.387(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.384(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.382(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.394(4) . ?
C38 H38 0.9500 . ?
C51 H51 0.9500 . ?
C51 C52 1.381(5) . ?
C51 C53 1.364(5) 2_566 ?
C52 H52 0.9500 . ?
C52 C53 1.371(5) . ?
C53 H53 0.9500 . ?
C61 H61 0.9500 . ?
C61 C62 1.372(5) . ?
C61 C63 1.388(5) 2_575 ?
C62 H62 0.9500 . ?
C62 C63 1.377(5) . ?
C63 H63 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
Cl2 Bi1 Cl1 170.725(19) . . ?
C2 Bi1 Cl1 88.91(7) . . ?
C2 Bi1 Cl2 85.48(7) . . ?
C2 Bi1 C15 119.38(9) . . ?
C2 Bi1 C21 127.71(9) . . ?
C15 Bi1 Cl1 88.26(6) . . ?
C15 Bi1 Cl2 88.06(6) . . ?
C15 Bi1 C21 112.80(9) . . ?
C21 Bi1 Cl1 96.08(7) . . ?
C21 Bi1 Cl2 93.19(7) . . ?
Cl4 Bi2 Cl3 175.59(2) . . ?
C13 Bi2 Cl3 91.39(7) . . ?
C13 Bi2 Cl4 89.29(7) . . ?
C27 Bi2 Cl3 90.69(9) . . ?
C27 Bi2 Cl4 91.67(9) . . ?
C27 Bi2 C13 138.46(10) . . ?
C33 Bi2 Cl3 87.62(7) . . ?
C33 Bi2 Cl4 88.07(7) . . ?
C33 Bi2 C13 110.94(10) . . ?
C33 Bi2 C27 110.60(11) . . ?
C14 O1 C1 127.87(19) . . ?
O1 C1 C2 113.8(2) . . ?
O1 C1 C6 126.8(2) . . ?
C2 C1 C6 119.4(2) . . ?
C1 C2 Bi1 116.30(17) . . ?
C3 C2 Bi1 119.50(19) . . ?
C3 C2 C1 122.6(2) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(2) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 118.5 . . ?
C4 C5 C6 123.1(3) . . ?
C6 C5 H5 118.5 . . ?
C1 C6 C7 121.7(2) . . ?
C5 C6 C1 117.1(3) . . ?
C5 C6 C7 120.5(2) . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C6 C7 C8 110.1(2) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 109.6(2) . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 C14 117.3(2) . . ?
C14 C9 C8 121.4(2) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 C9 122.8(3) . . ?
C11 C10 H10 118.6 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.3(3) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.9(3) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 Bi2 114.97(19) . . ?
C12 C13 C14 121.7(2) . . ?
C14 C13 Bi2 121.05(19) . . ?
O1 C14 C9 125.4(2) . . ?
O1 C14 C13 115.2(2) . . ?
C13 C14 C9 119.3(2) . . ?
C16 C15 Bi1 121.55(19) . . ?
C20 C15 Bi1 116.02(17) . . ?
C20 C15 C16 122.4(2) . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 118.0(3) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 118.6(2) . . ?
C15 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 Bi1 118.0(2) . . ?
C26 C21 Bi1 119.80(18) . . ?
C26 C21 C22 122.1(3) . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C23 118.7(3) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.9(3) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 118.1(3) . . ?
C21 C26 H26 120.9 . . ?
C25 C26 H26 120.9 . . ?
C28 C27 Bi2 120.7(2) . . ?
C28 C27 C32 123.0(3) . . ?
C32 C27 Bi2 116.1(3) . . ?
C27 C28 H28 121.0 . . ?
C27 C28 C29 118.0(3) . . ?
C29 C28 H28 121.0 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.3(4) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.2(3) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.8(4) . . ?
C32 C31 H31 119.6 . . ?
C27 C32 C31 117.7(4) . . ?
C27 C32 H32 121.2 . . ?
C31 C32 H32 121.2 . . ?
C34 C33 Bi2 117.5(2) . . ?
C34 C33 C38 121.3(3) . . ?
C38 C33 Bi2 121.1(2) . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.5(3) . . ?
C35 C34 H34 120.3 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0(3) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.4(3) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.1 . . ?
C36 C37 C38 119.9(3) . . ?
C38 C37 H37 120.1 . . ?
C33 C38 C37 118.9(3) . . ?
C33 C38 H38 120.5 . . ?
C37 C38 H38 120.5 . . ?
C52 C51 H51 120.0 . . ?
C53 C51 H51 120.0 2_566 . ?
C53 C51 C52 120.1(3) 2_566 . ?
C51 C52 H52 120.1 . . ?
C53 C52 C51 119.7(3) . . ?
C53 C52 H52 120.1 . . ?
C51 C53 C52 120.2(3) 2_566 . ?
C51 C53 H53 119.9 2_566 . ?
C52 C53 H53 119.9 . . ?
C62 C61 H61 120.0 . . ?
C62 C61 C63 120.0(4) . 2_575 ?
C63 C61 H61 120.0 2_575 . ?
C61 C62 H62 119.8 . . ?
C61 C62 C63 120.4(3) . . ?
C63 C62 H62 119.8 . . ?
C61 C63 H63 120.2 2_575 . ?
C62 C63 C61 119.6(4) . 2_575 ?
C62 C63 H63 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C2 C3 C4 -164.7(2) . . . . ?
Bi1 C15 C16 C17 -177.5(2) . . . . ?
Bi1 C15 C20 C19 176.90(19) . . . . ?
Bi1 C21 C22 C23 -175.1(3) . . . . ?
Bi1 C21 C26 C25 175.6(2) . . . . ?
Bi2 C13 C14 O1 -30.8(3) . . . . ?
Bi2 C13 C14 C9 153.4(2) . . . . ?
Bi2 C27 C28 C29 -175.5(2) . . . . ?
Bi2 C27 C32 C31 174.7(3) . . . . ?
Bi2 C33 C34 C35 -177.0(3) . . . . ?
Bi2 C33 C38 C37 175.6(2) . . . . ?
O1 C1 C2 Bi1 -22.3(3) . . . . ?
O1 C1 C2 C3 172.0(2) . . . . ?
O1 C1 C6 C5 -171.2(3) . . . . ?
O1 C1 C6 C7 18.4(4) . . . . ?
C1 O1 C14 C9 -30.1(4) . . . . ?
C1 O1 C14 C13 154.5(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C6 C7 C8 43.5(4) . . . . ?
C2 C1 C6 C5 7.6(4) . . . . ?
C2 C1 C6 C7 -162.8(3) . . . . ?
C2 C3 C4 C5 5.0(4) . . . . ?
C3 C4 C5 C6 -4.1(5) . . . . ?
C4 C5 C6 C1 -2.2(5) . . . . ?
C4 C5 C6 C7 168.3(3) . . . . ?
C5 C6 C7 C8 -126.5(3) . . . . ?
C6 C1 C2 Bi1 158.7(2) . . . . ?
C6 C1 C2 C3 -6.9(4) . . . . ?
C6 C7 C8 C9 -85.4(3) . . . . ?
C7 C8 C9 C10 -124.3(3) . . . . ?
C7 C8 C9 C14 46.6(3) . . . . ?
C8 C9 C10 C11 171.0(3) . . . . ?
C8 C9 C14 O1 20.8(4) . . . . ?
C8 C9 C14 C13 -163.9(3) . . . . ?
C9 C10 C11 C12 -5.7(5) . . . . ?
C10 C9 C14 O1 -168.0(2) . . . . ?
C10 C9 C14 C13 7.3(4) . . . . ?
C10 C11 C12 C13 4.5(4) . . . . ?
C11 C12 C13 Bi2 -160.4(2) . . . . ?
C11 C12 C13 C14 2.6(4) . . . . ?
C12 C13 C14 O1 167.2(2) . . . . ?
C12 C13 C14 C9 -8.6(4) . . . . ?
C14 O1 C1 C2 163.1(2) . . . . ?
C14 O1 C1 C6 -18.1(4) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C15 C20 C19 -0.5(4) . . . . ?
C16 C17 C18 C19 -1.0(5) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C19 C20 C15 0.5(4) . . . . ?
C20 C15 C16 C17 -0.2(4) . . . . ?
C21 C22 C23 C24 -0.1(7) . . . . ?
C22 C21 C26 C25 -0.2(5) . . . . ?
C22 C23 C24 C25 -1.3(6) . . . . ?
C23 C24 C25 C26 1.9(5) . . . . ?
C24 C25 C26 C21 -1.2(5) . . . . ?
C26 C21 C22 C23 0.8(6) . . . . ?
C27 C28 C29 C30 1.4(5) . . . . ?
C28 C27 C32 C31 -0.6(6) . . . . ?
C28 C29 C30 C31 -1.4(7) . . . . ?
C29 C30 C31 C32 0.3(8) . . . . ?
C30 C31 C32 C27 0.7(7) . . . . ?
C32 C27 C28 C29 -0.5(5) . . . . ?
C33 C34 C35 C36 1.0(6) . . . . ?
C34 C33 C38 C37 -2.3(5) . . . . ?
C34 C35 C36 C37 -1.8(6) . . . . ?
C35 C36 C37 C38 0.5(5) . . . . ?
C36 C37 C38 C33 1.5(5) . . . . ?
C38 C33 C34 C35 1.1(5) . . . . ?
C51 C52 C53 C51 -0.1(7) . . . 2_566 ?
C53 C51 C52 C53 0.1(7) 2_566 . . . ?
C61 C62 C63 C61 -0.2(5) . . . 2_575 ?
C63 C61 C62 C63 0.2(6) 2_575 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_shelx_SHELXL_version_number     2018/3
####################################################################### 
# 
# 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_13364sadabs
_database_code_depnum_ccdc_archive 'CCDC 2063978'
loop_
_audit_author_name
_audit_author_address
'Nils Noethling'
;Max Planck Institut fuer Kohlenforschung
Germany
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_block_code                KUJ-KA-131-01
_audit_creation_date             2020-08-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
4,6-bis(diphenylbismuthanyl)-10,11-dihydrodibenzo[b,f]oxepine
;
_chemical_formula_moiety         'C38 H30 Bi2 O'
_chemical_formula_sum            'C38 H30 Bi2 O'
_chemical_formula_weight         920.58
_chemical_properties_physical    none
_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'
O O 0.0106 0.0060 '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                   10.6951(17)
_cell_length_b                   10.8286(12)
_cell_length_c                   13.7009(8)
_cell_angle_alpha                83.462(6)
_cell_angle_beta                 88.592(9)
_cell_angle_gamma                79.178(12)
_cell_volume                     1548.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    49119


_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.0996
_cell_measurement_theta_min      2.771
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    11.378
_exptl_absorpt_correction_T_max  0.68309
_exptl_absorpt_correction_T_min  0.47746

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_exptl_crystal_description       prism
_exptl_crystal_F_000             864

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0200
0.00 1.00 1.00 0.0200
1.00 0.00 0.00 0.0350
-1.00 0.00 0.00 0.0350
0.00 1.00 -1.00 0.0250
0.00 -1.00 1.00 0.0250
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  dichloromethane, hexane'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47337
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.080
_diffrn_reflns_theta_min         2.768

_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8776
_reflns_number_total             11728
_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       'EVALCCD V. 1.6, 2008'

_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'EVALCCD V. 1.6, 2008'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.781
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         11728
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0188P)²+1.7413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0613

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.4830 and 0.6881 (SADABS).

INTENSITY STATISTICS FOR DATASET 	
#------------------------------------------------------------------------------- 
Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 2.60     176    184     95.7     8.72    140.68   63.91  0.0360  0.0124
 2.60 - 1.75     419    419    100.0     6.29    102.07   46.48  0.0312  0.0163
 1.75 - 1.40     584    584    100.0     5.68     73.63   38.69  0.0337  0.0190
 1.40 - 1.22     597    597    100.0     5.35     51.08   31.55  0.0365  0.0224
 1.22 - 1.11     591    591    100.0     5.04     43.27   27.54  0.0371  0.0252
 1.11 - 1.03     595    595    100.0     4.85     36.74   24.02  0.0396  0.0288
 1.03 - 0.97     564    564    100.0     4.55     29.10   20.28  0.0455  0.0338
 0.97 - 0.92     628    628    100.0     4.44     26.32   18.54  0.0491  0.0380
 0.92 - 0.88     599    599    100.0     4.23     23.14   16.89  0.0563  0.0436
 0.88 - 0.84     710    710    100.0     3.94     18.12   13.57  0.0673  0.0534
 0.84 - 0.82     412    412    100.0     3.81     17.62   12.66  0.0667  0.0575
 0.82 - 0.79     707    707    100.0     3.72     13.90   10.81  0.0828  0.0697
 0.79 - 0.77     504    504    100.0     3.48     13.18    9.90  0.0883  0.0779
 0.77 - 0.75     590    590    100.0     3.42     11.46    8.66  0.1088  0.0905
 0.75 - 0.73     663    663    100.0     3.26     11.17    7.89  0.1150  0.0996
 0.73 - 0.71     717    717    100.0     3.10      9.60    6.91  0.1343  0.1220
 0.71 - 0.70     403    403    100.0     3.08      9.82    6.74  0.1283  0.1272
 0.70 - 0.68     834    834    100.0     2.94      7.09    4.87  0.1727  0.1846
 0.68 - 0.67     483    483    100.0     2.84      6.68    4.24  0.2018  0.2225
 0.67 - 0.66     488    488    100.0     2.78      6.32    3.84  0.2072  0.2548
 0.66 - 0.65     464    482     96.3     2.60      5.41    3.03  0.2528  0.3300
#-------------------------------------------------------------------------------
 0.75 - 0.65    4052   4070     99.6     2.96      8.14    5.50  0.1557  0.1669
  Inf - 0.65   11728  11754     99.8     4.03     26.57   16.27  0.0489  0.0449
#-------------------------------------------------------------------------------

 Highest peak    1.34  at  0.4616  0.6773  0.1753  [  0.89 A from BI1 ]
 Deepest hole   -1.78  at  0.4413  0.7010  0.1037  [  0.71 A from BI1 ]
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C12(H12), C34(H34), C28(H28), C13(H13), C26(H26), C2(H2), C22(H22),
 C29(H29), C31(H31), C20(H20), C19(H19), C32(H32), C16(H16), C38(H38), C35(H35),
  C14(H14), C25(H25), C36(H36), C17(H17), C23(H23), C37(H37), C18(H18), C3(H3),
 C24(H24), C4(H4)
;
_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Bi2 Bi 0.32395(2) 0.46716(2) 0.64265(2) 0.01953(3) Uani 1 1 d . . . . .
Bi1 Bi 0.50079(2) 0.33920(2) 0.88147(2) 0.02134(3) Uani 1 1 d . . . . .
O1 O 0.1902(2) 0.3852(2) 0.83985(17) 0.0221(5) Uani 1 1 d . . . . .
C21 C 0.5217(3) 0.1908(3) 0.7772(3) 0.0220(7) Uani 1 1 d . . . . .
C27 C 0.3270(3) 0.4446(3) 0.4807(3) 0.0225(7) Uani 1 1 d . . . . .
C10 C 0.1307(3) 0.3268(3) 0.7715(3) 0.0198(6) Uani 1 1 d . . . . .
C30 C 0.3380(4) 0.4095(4) 0.2812(3) 0.0287(8) Uani 1 1 d . . . . .
H30 H 0.341807 0.398662 0.213272 0.034 Uiso 1 1 calc R U . . .
C1 C 0.3355(3) 0.2829(3) 0.9690(2) 0.0203(6) Uani 1 1 d . . . . .
C33 C 0.1741(3) 0.6459(3) 0.6279(2) 0.0213(7) Uani 1 1 d . . . . .
C12 C 0.1308(3) 0.2852(3) 0.6025(3) 0.0221(7) Uani 1 1 d . . . . .
H12 H 0.162858 0.294805 0.537382 0.027 Uiso 1 1 calc R U . . .
C34 C 0.0462(3) 0.6465(3) 0.6490(3) 0.0231(7) Uani 1 1 d . . . . .
H34 H 0.017777 0.568634 0.664655 0.028 Uiso 1 1 calc R U . . .
C9 C 0.0271(3) 0.2652(3) 0.7927(3) 0.0231(7) Uani 1 1 d . . . . .
C11 C 0.1794(3) 0.3412(3) 0.6756(2) 0.0205(7) Uani 1 1 d . . . . .
C28 C 0.4198(3) 0.3518(4) 0.4453(3) 0.0279(8) Uani 1 1 d . . . . .
H28 H 0.479952 0.299874 0.489485 0.034 Uiso 1 1 calc R U . . .
C13 C 0.0348(3) 0.2147(3) 0.6241(3) 0.0251(7) Uani 1 1 d . . . . .
H13 H 0.004392 0.172757 0.574898 0.030 Uiso 1 1 calc R U . . .
C26 C 0.4435(4) 0.1009(4) 0.7810(3) 0.0284(8) Uani 1 1 d . . . . .
H26 H 0.379145 0.099992 0.829962 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2109(3) 0.3244(3) 0.9366(2) 0.0213(7) Uani 1 1 d . . . . .
C2 C 0.3538(4) 0.2205(3) 1.0645(3) 0.0238(7) Uani 1 1 d . . . . .
H2 H 0.437838 0.189542 1.088309 0.029 Uiso 1 1 calc R U . . .
C22 C 0.6157(4) 0.1904(4) 0.7046(3) 0.0297(8) Uani 1 1 d . . . . .
H22 H 0.668647 0.252095 0.700454 0.036 Uiso 1 1 calc R U . . .
C29 C 0.4258(4) 0.3339(4) 0.3459(3) 0.0323(9) Uani 1 1 d . . . . .
H29 H 0.489619 0.270445 0.322700 0.039 Uiso 1 1 calc R U . . .
C15 C 0.6436(3) 0.2235(3) 0.9901(3) 0.0236(7) Uani 1 1 d . . . . .
C7 C -0.0254(4) 0.3590(4) 0.9565(3) 0.0336(9) Uani 1 1 d . . . . .
H7A H -0.032392 0.444726 0.920680 0.040 Uiso 1 1 calc R U . . .
H7B H -0.088563 0.363099 1.010640 0.040 Uiso 1 1 calc R U . . .
C31 C 0.2451(4) 0.5005(4) 0.3160(3) 0.0293(8) Uani 1 1 d . . . . .
H31 H 0.184235 0.551599 0.271903 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6803(4) 0.2811(4) 1.0680(3) 0.0302(8) Uani 1 1 d . . . . .
H20 H 0.645398 0.367272 1.074135 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7680(4) 0.2126(4) 1.1371(3) 0.0345(9) Uani 1 1 d . . . . .
H19 H 0.791848 0.252186 1.190359 0.041 Uiso 1 1 calc R U . . .
C32 C 0.2398(4) 0.5180(3) 0.4146(3) 0.0273(8) Uani 1 1 d . . . . .
H32 H 0.175399 0.581306 0.437363 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6965(3) 0.0979(3) 0.9815(3) 0.0265(8) Uani 1 1 d . . . . .
H16 H 0.672642 0.058158 0.928331 0.032 Uiso 1 1 calc R U . . .
C38 C 0.2129(3) 0.7622(3) 0.6045(3) 0.0242(7) Uani 1 1 d . . . . .
H38 H 0.299712 0.763871 0.589143 0.029 Uiso 1 1 calc R U . . .
C8 C -0.0518(3) 0.2664(4) 0.8868(3) 0.0303(8) Uani 1 1 d . . . . .
H8A H -0.035955 0.180055 0.922289 0.036 Uiso 1 1 calc R U . . .
H8B H -0.143080 0.287529 0.868809 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1059(3) 0.3148(3) 0.9973(3) 0.0258(7) Uani 1 1 d . . . . .
C35 C -0.0407(4) 0.7600(4) 0.6474(3) 0.0266(7) Uani 1 1 d . . . . .
H35 H -0.127953 0.759010 0.661561 0.032 Uiso 1 1 calc R U . . .
C14 C -0.0150(3) 0.2067(3) 0.7175(3) 0.0256(7) Uani 1 1 d . . . . .
H14 H -0.080924 0.159396 0.731429 0.031 Uiso 1 1 calc R U . . .
C25 C 0.4591(4) 0.0127(4) 0.7137(3) 0.0381(10) Uani 1 1 d . . . . .
H25 H 0.404621 -0.047545 0.716212 0.046 Uiso 1 1 calc R U . . .
C36 C -0.0002(4) 0.8742(4) 0.6252(3) 0.0285(8) Uani 1 1 d . . . . .
H36 H -0.059225 0.951611 0.624828 0.034 Uiso 1 1 calc R U . . .
C17 C 0.7842(4) 0.0300(4) 1.0504(3) 0.0303(8) Uani 1 1 d . . . . .
H17 H 0.819571 -0.056041 1.044231 0.036 Uiso 1 1 calc R U . . .
C23 C 0.6324(4) 0.1007(4) 0.6384(3) 0.0381(10) Uani 1 1 d . . . . .
H23 H 0.697771 0.100220 0.590132 0.046 Uiso 1 1 calc R U . . .
C37 C 0.1265(4) 0.8750(3) 0.6035(3) 0.0289(8) Uani 1 1 d . . . . .
H37 H 0.154399 0.953196 0.587812 0.035 Uiso 1 1 calc R U . . .
C18 C 0.8203(4) 0.0879(4) 1.1284(3) 0.0349(9) Uani 1 1 d . . . . .
H18 H 0.880512 0.041621 1.175220 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2510(4) 0.2037(4) 1.1243(3) 0.0277(8) Uani 1 1 d . . . . .
H3 H 0.264736 0.158699 1.187953 0.033 Uiso 1 1 calc R U . . .
C24 C 0.5543(5) 0.0119(4) 0.6424(3) 0.0416(11) Uani 1 1 d . . . . .
H24 H 0.565472 -0.049198 0.596887 0.050 Uiso 1 1 calc R U . . .
C4 C 0.1276(4) 0.2523(4) 1.0919(3) 0.0284(8) Uani 1 1 d . . . . .
H4 H 0.057596 0.242920 1.134293 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi2 C27 2.259(4) . ?
Bi2 C33 2.262(3) . ?
Bi2 C11 2.252(3) . ?
Bi1 C21 2.247(4) . ?
Bi1 C1 2.251(3) . ?
Bi1 C15 2.255(3) . ?
O1 C10 1.413(4) . ?
O1 C6 1.415(4) . ?
C21 C26 1.393(5) . ?
C21 C22 1.397(5) . ?
C27 C28 1.394(5) . ?
C27 C32 1.386(5) . ?
C10 C9 1.405(5) . ?
C10 C11 1.404(5) . ?
C30 H30 0.9500 . ?
C30 C29 1.388(6) . ?
C30 C31 1.378(6) . ?
C1 C6 1.390(5) . ?
C1 C2 1.403(5) . ?
C33 C34 1.390(5) . ?
C33 C38 1.400(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(5) . ?
C12 C13 1.397(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.393(5) . ?
C9 C8 1.523(5) . ?
C9 C14 1.394(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.395(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(5) . ?
C26 H26 0.9500 . ?
C26 C25 1.387(6) . ?
C6 C5 1.393(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(6) . ?
C29 H29 0.9500 . ?
C15 C20 1.396(5) . ?
C15 C16 1.388(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.529(6) . ?
C7 C5 1.496(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.384(5) . ?
C20 H20 0.9500 . ?
C20 C19 1.396(5) . ?
C19 H19 0.9500 . ?
C19 C18 1.379(6) . ?
C32 H32 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.392(5) . ?
C38 H38 0.9500 . ?
C38 C37 1.385(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C5 C4 1.395(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.386(5) . ?
C14 H14 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.392(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.381(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.396(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(7) . ?
C37 H37 0.9500 . ?
C18 H18 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.389(5) . ?
C24 H24 0.9500 . ?
C4 H4 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
C27 Bi2 C33 94.34(12) . . ?
C11 Bi2 C27 92.72(12) . . ?
C11 Bi2 C33 93.21(12) . . ?
C21 Bi1 C1 97.62(12) . . ?
C21 Bi1 C15 94.52(13) . . ?
C1 Bi1 C15 92.32(12) . . ?
C10 O1 C6 118.8(3) . . ?
C26 C21 Bi1 122.8(3) . . ?
C26 C21 C22 118.9(4) . . ?
C22 C21 Bi1 118.4(3) . . ?
C28 C27 Bi2 118.8(3) . . ?
C32 C27 Bi2 123.0(3) . . ?
C32 C27 C28 118.2(3) . . ?
C9 C10 O1 125.0(3) . . ?
C11 C10 O1 114.0(3) . . ?
C11 C10 C9 121.0(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C31 C30 C29 119.6(4) . . ?
C6 C1 Bi1 121.3(2) . . ?
C6 C1 C2 117.6(3) . . ?
C2 C1 Bi1 120.5(2) . . ?
C34 C33 Bi2 122.9(2) . . ?
C34 C33 C38 118.2(3) . . ?
C38 C33 Bi2 118.7(3) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C33 C34 H34 119.6 . . ?
C33 C34 C35 120.9(3) . . ?
C35 C34 H34 119.6 . . ?
C10 C9 C8 126.3(3) . . ?
C14 C9 C10 117.1(3) . . ?
C14 C9 C8 116.4(3) . . ?
C10 C11 Bi2 118.8(2) . . ?
C12 C11 Bi2 121.8(3) . . ?
C12 C11 C10 119.3(3) . . ?
C27 C28 H28 119.5 . . ?
C27 C28 C29 121.0(4) . . ?
C29 C28 H28 119.5 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.4(4) . . ?
C25 C26 H26 119.8 . . ?
C1 C6 O1 118.6(3) . . ?
C1 C6 C5 122.6(3) . . ?
C5 C6 O1 118.7(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(4) . . ?
C23 C22 H22 119.7 . . ?
C30 C29 C28 119.6(4) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C20 C15 Bi1 118.5(3) . . ?
C16 C15 Bi1 122.3(3) . . ?
C16 C15 C20 119.2(3) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C5 C7 H7A 109.9 . . ?
C5 C7 H7B 109.9 . . ?
C5 C7 C8 108.8(3) . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.5(4) . . ?
C32 C31 H31 119.7 . . ?
C15 C20 H20 119.9 . . ?
C15 C20 C19 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C27 C32 H32 119.5 . . ?
C31 C32 C27 121.0(4) . . ?
C31 C32 H32 119.5 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C33 C38 H38 119.5 . . ?
C37 C38 C33 120.9(3) . . ?
C37 C38 H38 119.5 . . ?
C9 C8 C7 115.0(3) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C6 C5 C7 119.5(3) . . ?
C6 C5 C4 118.1(3) . . ?
C4 C5 C7 122.1(3) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.1(4) . . ?
C36 C35 H35 120.0 . . ?
C9 C14 H14 118.6 . . ?
C13 C14 C9 122.7(3) . . ?
C13 C14 H14 118.6 . . ?
C26 C25 H25 119.8 . . ?
C26 C25 C24 120.3(4) . . ?
C24 C25 H25 119.8 . . ?
C35 C36 H36 120.1 . . ?
C37 C36 C35 119.7(3) . . ?
C37 C36 H36 120.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.3(4) . . ?
C18 C17 H17 119.9 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(4) . . ?
C24 C23 H23 119.9 . . ?
C38 C37 H37 119.9 . . ?
C36 C37 C38 120.2(3) . . ?
C36 C37 H37 119.9 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C25 C24 H24 120.2 . . ?
C23 C24 C25 119.6(4) . . ?
C23 C24 H24 120.2 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi2 C27 C28 C29 180.0(3) . . . . ?
Bi2 C27 C32 C31 -179.8(3) . . . . ?
Bi2 C33 C34 C35 174.1(3) . . . . ?
Bi2 C33 C38 C37 -174.0(3) . . . . ?
Bi1 C21 C26 C25 178.9(3) . . . . ?
Bi1 C21 C22 C23 180.0(3) . . . . ?
Bi1 C1 C6 O1 10.5(4) . . . . ?
Bi1 C1 C6 C5 -165.8(3) . . . . ?
Bi1 C1 C2 C3 169.6(3) . . . . ?
Bi1 C15 C20 C19 179.7(3) . . . . ?
Bi1 C15 C16 C17 -179.9(3) . . . . ?
O1 C10 C9 C8 9.6(5) . . . . ?
O1 C10 C9 C14 -176.6(3) . . . . ?
O1 C10 C11 Bi2 -6.3(4) . . . . ?
O1 C10 C11 C12 178.4(3) . . . . ?
O1 C6 C5 C7 5.0(5) . . . . ?
O1 C6 C5 C4 178.7(3) . . . . ?
C21 C26 C25 C24 0.9(6) . . . . ?
C21 C22 C23 C24 1.3(6) . . . . ?
C27 C28 C29 C30 -0.1(6) . . . . ?
C10 O1 C6 C1 115.5(3) . . . . ?
C10 O1 C6 C5 -68.0(4) . . . . ?
C10 C9 C8 C7 9.1(5) . . . . ?
C10 C9 C14 C13 -4.4(5) . . . . ?
C30 C31 C32 C27 -0.2(6) . . . . ?
C1 C6 C5 C7 -178.7(3) . . . . ?
C1 C6 C5 C4 -5.0(5) . . . . ?
C1 C2 C3 C4 -2.2(6) . . . . ?
C33 C34 C35 C36 -0.4(6) . . . . ?
C33 C38 C37 C36 -0.3(6) . . . . ?
C12 C13 C14 C9 -0.7(5) . . . . ?
C34 C33 C38 C37 0.7(5) . . . . ?
C34 C35 C36 C37 0.8(6) . . . . ?
C9 C10 C11 Bi2 170.4(2) . . . . ?
C9 C10 C11 C12 -5.0(5) . . . . ?
C11 C10 C9 C8 -166.6(3) . . . . ?
C11 C10 C9 C14 7.2(5) . . . . ?
C11 C12 C13 C14 3.2(5) . . . . ?
C28 C27 C32 C31 -0.5(5) . . . . ?
C13 C12 C11 Bi2 -175.5(2) . . . . ?
C13 C12 C11 C10 -0.3(5) . . . . ?
C26 C21 C22 C23 -1.1(5) . . . . ?
C26 C25 C24 C23 -0.7(6) . . . . ?
C6 O1 C10 C9 40.8(4) . . . . ?
C6 O1 C10 C11 -142.8(3) . . . . ?
C6 C1 C2 C3 -1.2(5) . . . . ?
C6 C5 C4 C3 1.3(6) . . . . ?
C2 C1 C6 O1 -178.7(3) . . . . ?
C2 C1 C6 C5 4.9(5) . . . . ?
C2 C3 C4 C5 2.2(6) . . . . ?
C22 C21 C26 C25 0.0(5) . . . . ?
C22 C23 C24 C25 -0.3(6) . . . . ?
C29 C30 C31 C32 0.8(6) . . . . ?
C15 C20 C19 C18 0.7(6) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C7 C5 C4 C3 174.8(4) . . . . ?
C31 C30 C29 C28 -0.6(6) . . . . ?
C20 C15 C16 C17 0.6(6) . . . . ?
C20 C19 C18 C17 -0.5(7) . . . . ?
C32 C27 C28 C29 0.7(5) . . . . ?
C16 C15 C20 C19 -0.7(6) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C38 C33 C34 C35 -0.3(5) . . . . ?
C8 C9 C14 C13 170.1(3) . . . . ?
C8 C7 C5 C6 71.5(4) . . . . ?
C8 C7 C5 C4 -102.0(4) . . . . ?
C5 C7 C8 C9 -67.7(4) . . . . ?
C35 C36 C37 C38 -0.4(6) . . . . ?
C14 C9 C8 C7 -164.7(3) . . . . ?

_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_13015sadabs
_database_code_depnum_ccdc_archive 'CCDC 2063975'
loop_
_audit_author_name
_audit_author_address
'Nils Noethling'
;Max Planck Institut fuer Kohlenforschung
Germany
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_block_code                MBH-MA-009-01
_audit_creation_date             2020-03-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylbismuthane)
;
_chemical_formula_moiety         'C39 H32 Bi2 O'
_chemical_formula_sum            'C39 H32 Bi2 O'
_chemical_formula_weight         934.60
_chemical_absolute_configuration ad
_chemical_properties_physical    none
_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'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   37.8761(11)
_cell_length_b                   51.1850(17)
_cell_length_c                   6.6097(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12814.1(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9186

_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7691
_cell_measurement_theta_min      2.6759
_shelx_estimated_absorpt_T_max   0.802
_shelx_estimated_absorpt_T_min   0.699
_exptl_absorpt_coefficient_mu    11.000
_exptl_absorpt_correction_T_max  0.85446
_exptl_absorpt_correction_T_min  0.72004

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  dichloromethane, pentane'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 1.00 0.0150
-1.00 0.00 -1.00 0.0150
1.00 0.00 0.00 0.0100
-1.00 0.00 0.00 0.0150
0.00 1.00 0.00 0.0050
0.00 -1.00 0.00 0.0100

_exptl_crystal_description       prism
_exptl_crystal_F_000             7040
_exptl_crystal_size_max          0.035
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       76
_diffrn_reflns_limit_k_min       -76
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            112958
_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         32.028
_diffrn_reflns_theta_min         1.338

_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         1\mS
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                9565
_reflns_number_total             11150
_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       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'APEX3 (Bruker AXS, 2005-2017)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_refine_diff_density_max         0.868
_refine_diff_density_min         -1.262
_refine_diff_density_rms         0.155
_refine_ls_abs_structure_details 
;
 Flack x determined using 3932 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         11150
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0111P)²+22.1937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0415
_refine_ls_wR_factor_ref         0.0437

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.6829 and 0.8678 (SADABS).

INTENSITY STATISTICS FOR DATASET 	
#------------------------------------------------------------------------------- 
Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 2.66     200    201     99.5    16.96     95.19   68.76  0.0220  0.0116
 2.66 - 1.75     463    463    100.0    18.49     70.61   65.58  0.0274  0.0125
 1.75 - 1.38     671    671    100.0    18.31     45.20   52.21  0.0388  0.0156
 1.38 - 1.20     695    695    100.0    18.26     37.69   45.16  0.0481  0.0180
 1.20 - 1.09     645    645    100.0    16.62     27.11   34.02  0.0651  0.0239
 1.09 - 1.01     703    703    100.0    12.42     25.28   25.97  0.0736  0.0309
 1.01 - 0.95     656    656    100.0    10.20     21.96   21.40  0.0885  0.0399
 0.95 - 0.90     714    714    100.0     8.84     17.50   16.32  0.1038  0.0517
 0.90 - 0.86     682    682    100.0     7.95     14.48   13.41  0.1218  0.0650
 0.86 - 0.83     592    592    100.0     7.70     12.60   11.82  0.1369  0.0759
 0.83 - 0.80     703    703    100.0     7.15     12.03   10.28  0.1521  0.0841
 0.80 - 0.78     541    541    100.0     7.03     10.33    8.97  0.1652  0.0981
 0.78 - 0.75     897    897    100.0     6.82      9.33    8.03  0.1877  0.1123
 0.75 - 0.73     664    664    100.0     6.61      7.82    6.62  0.2204  0.1371
 0.73 - 0.71     783    784     99.9     6.26      7.07    5.81  0.2493  0.1573
 0.71 - 0.70     438    438    100.0     6.16      6.44    5.20  0.2553  0.1765
 0.70 - 0.68     875    876     99.9     6.04      5.64    4.60  0.2969  0.2071
 0.68 - 0.67     476    479     99.4     5.84      5.22    4.11  0.3323  0.2332
 0.67 - 0.66     484    492     98.4     5.71      4.70    3.69  0.3623  0.2616
 0.66 - 0.64    1164   1194     97.5     4.90      3.96    2.87  0.3944  0.3500
 0.64 - 0.63     144    456     31.6     0.57      2.74    1.14  0.4023  1.0221
#-------------------------------------------------------------------------------
 0.73 - 0.63    4364   4719     92.5     5.22      5.28    4.15  0.3079  0.2421
  Inf - 0.63   13190  13546     97.4     9.10     18.07   17.77  0.0694  0.0565
#-------------------------------------------------------------------------------

 Highest peak    1.06  at  0.3591  0.9192  0.6362  [  1.14 A from BI2 ]
 Deepest hole   -1.74  at  0.8605  0.4367  0.5360  [  0.08 A from BI2 ]
;
_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:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

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 0.37776(2) 0.61781(2) 0.46220(3) 0.01950(5) Uani 1 1 d . . . . .
Bi2 Bi 0.39139(2) 0.68736(2) 0.78653(3) 0.01698(5) Uani 1 1 d . . . . .
O1 O 0.33708(8) 0.67329(7) 0.4335(6) 0.0159(8) Uani 1 1 d . . . . .
C1 C 0.32770(12) 0.66064(10) 0.2560(8) 0.0163(12) Uani 1 1 d . . . . .
C2 C 0.34103(13) 0.63541(10) 0.2279(9) 0.0182(11) Uani 1 1 d . . . . .
C3 C 0.33257(14) 0.62234(10) 0.0538(10) 0.0211(12) Uani 1 1 d . . . . .
H3 H 0.341322 0.605166 0.032327 0.025 Uiso 1 1 calc R U . . .
C4 C 0.31128(14) 0.63401(11) -0.0919(9) 0.0232(13) Uani 1 1 d . . . . .
H4 H 0.305681 0.624809 -0.212541 0.028 Uiso 1 1 calc R U . . .
C5 C 0.29813(13) 0.65909(11) -0.0619(9) 0.0205(12) Uani 1 1 d . . . . .
H5 H 0.283846 0.666932 -0.163222 0.025 Uiso 1 1 calc R U . . .
C6 C 0.30563(12) 0.67290(10) 0.1151(8) 0.0171(11) Uani 1 1 d . . . . .
C7 C 0.29019(13) 0.69967(10) 0.1625(8) 0.0178(11) Uani 1 1 d . . . . .
C8 C 0.31707(12) 0.71422(10) 0.2917(9) 0.0164(10) Uani 1 1 d . . . . .
C9 C 0.32059(13) 0.74151(10) 0.2912(10) 0.0200(11) Uani 1 1 d . . . . .
H9 H 0.306866 0.751597 0.199693 0.024 Uiso 1 1 calc R U . . .
C10 C 0.34379(14) 0.75410(10) 0.4222(9) 0.0200(12) Uani 1 1 d . . . . .
H10 H 0.345845 0.772597 0.420133 0.024 Uiso 1 1 calc R U . . .
C11 C 0.36390(13) 0.73941(11) 0.5561(10) 0.0224(12) Uani 1 1 d . . . . .
H11 H 0.379586 0.748083 0.645878 0.027 Uiso 1 1 calc R U . . .
C12 C 0.36161(13) 0.71212(10) 0.5618(9) 0.0172(11) Uani 1 1 d . . . . .
C13 C 0.33819(12) 0.70044(9) 0.4265(8) 0.0149(11) Uani 1 1 d . . . . .
C14 C 0.25660(13) 0.69563(11) 0.2903(11) 0.0288(14) Uani 1 1 d . . . . .
H14A H 0.262571 0.685969 0.413643 0.043 Uiso 1 1 calc R U . . .
H14B H 0.239240 0.685695 0.211794 0.043 Uiso 1 1 calc R U . . .
H14C H 0.246641 0.712663 0.326724 0.043 Uiso 1 1 calc R U . . .
C15 C 0.28071(14) 0.71477(12) -0.0297(10) 0.0296(14) Uani 1 1 d . . . . .
H15A H 0.272108 0.732200 0.006900 0.044 Uiso 1 1 calc R U . . .
H15B H 0.262252 0.705358 -0.103671 0.044 Uiso 1 1 calc R U . . .
H15C H 0.301709 0.716438 -0.115367 0.044 Uiso 1 1 calc R U . . .
C16 C 0.34019(13) 0.58680(10) 0.5693(8) 0.0179(11) Uani 1 1 d . . . . .
C17 C 0.35115(14) 0.57073(11) 0.7254(9) 0.0228(13) Uani 1 1 d . . . . .
H17 H 0.374927 0.571587 0.770728 0.027 Uiso 1 1 calc R U . . .
C18 C 0.32777(14) 0.55324(10) 0.8177(9) 0.0220(13) Uani 1 1 d . . . . .
H18 H 0.335665 0.542287 0.924558 0.026 Uiso 1 1 calc R U . . .
C19 C 0.29332(14) 0.55197(11) 0.7529(9) 0.0233(13) Uani 1 1 d . . . . .
H19 H 0.277200 0.540367 0.816541 0.028 Uiso 1 1 calc R U . . .
C20 C 0.28213(14) 0.56774(11) 0.5937(9) 0.0224(13) Uani 1 1 d . . . . .
H20 H 0.258379 0.566757 0.548166 0.027 Uiso 1 1 calc R U . . .
C21 C 0.30553(13) 0.58494(10) 0.5010(8) 0.0184(12) Uani 1 1 d . . . . .
H21 H 0.297838 0.595416 0.390859 0.022 Uiso 1 1 calc R U . . .
C22 C 0.40451(12) 0.59119(10) 0.2361(9) 0.0199(12) Uani 1 1 d . . . . .
C23 C 0.42760(15) 0.60173(12) 0.0936(10) 0.0313(15) Uani 1 1 d . . . . .
H23 H 0.430608 0.620136 0.087459 0.038 Uiso 1 1 calc R U . . .
C24 C 0.44619(14) 0.58608(12) -0.0387(11) 0.0302(15) Uani 1 1 d . . . . .
H24 H 0.461528 0.593707 -0.135905 0.036 Uiso 1 1 calc R U . . .
C25 C 0.44238(13) 0.55901(12) -0.0292(10) 0.0270(14) Uani 1 1 d . . . . .
H25 H 0.455343 0.548062 -0.118304 0.032 Uiso 1 1 calc R U . . .
C26 C 0.41959(15) 0.54828(11) 0.1111(9) 0.0245(13) Uani 1 1 d . . . . .
H26 H 0.416578 0.529864 0.116188 0.029 Uiso 1 1 calc R U . . .
C27 C 0.40097(14) 0.56409(10) 0.2450(9) 0.0201(12) Uani 1 1 d . . . . .
H27 H 0.385811 0.556401 0.342754 0.024 Uiso 1 1 calc R U . . .
C28 C 0.42293(14) 0.72226(10) 0.8832(8) 0.0188(11) Uani 1 1 d . . . . .
C29 C 0.40943(13) 0.73861(11) 1.0343(10) 0.0228(12) Uani 1 1 d . . . . .
H29 H 0.387732 0.734211 1.097814 0.027 Uiso 1 1 calc R U . . .
C30 C 0.42704(14) 0.76103(12) 1.0929(9) 0.0244(14) Uani 1 1 d . . . . .
H30 H 0.417250 0.772062 1.193985 0.029 Uiso 1 1 calc R U . . .
C31 C 0.45923(14) 0.76738(11) 1.0031(9) 0.0252(14) Uani 1 1 d . . . . .
H31 H 0.471409 0.782792 1.042395 0.030 Uiso 1 1 calc R U . . .
C32 C 0.47337(14) 0.75118(10) 0.8567(8) 0.0201(12) Uani 1 1 d . . . . .
H32 H 0.495553 0.755298 0.797739 0.024 Uiso 1 1 calc R U . . .
C33 C 0.45533(12) 0.72894(10) 0.7955(9) 0.0184(11) Uani 1 1 d . . . . .
H33 H 0.465090 0.718125 0.692869 0.022 Uiso 1 1 calc R U . . .
C34 C 0.43270(13) 0.67427(10) 0.5635(9) 0.0174(11) Uani 1 1 d . . . . .
C35 C 0.45435(14) 0.65318(11) 0.6143(10) 0.0228(13) Uani 1 1 d . . . . .
H35 H 0.451958 0.645172 0.743212 0.027 Uiso 1 1 calc R U . . .
C36 C 0.47930(13) 0.64377(11) 0.4791(10) 0.0273(14) Uani 1 1 d . . . . .
H36 H 0.493499 0.629173 0.514650 0.033 Uiso 1 1 calc R U . . .
C37 C 0.48354(13) 0.65563(12) 0.2919(10) 0.0281(13) Uani 1 1 d . . . . .
H37 H 0.500793 0.649467 0.199159 0.034 Uiso 1 1 calc R U . . .
C38 C 0.46210(14) 0.67669(12) 0.2430(9) 0.0280(14) Uani 1 1 d . . . . .
H38 H 0.465005 0.685049 0.115721 0.034 Uiso 1 1 calc R U . . .
C39 C 0.43684(14) 0.68569(11) 0.3739(9) 0.0227(12) Uani 1 1 d . . . . .
H39 H 0.422060 0.699815 0.335011 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C2 2.268(6) . ?
Bi1 C16 2.246(5) . ?
Bi1 C22 2.262(5) . ?
Bi2 C12 2.255(5) . ?
Bi2 C28 2.242(5) . ?
Bi2 C34 2.252(5) . ?
O1 C1 1.387(6) . ?
O1 C13 1.391(6) . ?
C1 C2 1.399(7) . ?
C1 C6 1.400(7) . ?
C2 C3 1.369(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(8) . ?
C6 C7 1.522(7) . ?
C7 C8 1.523(7) . ?
C7 C14 1.541(8) . ?
C7 C15 1.530(8) . ?
C8 C9 1.403(7) . ?
C8 C13 1.390(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(7) . ?
C12 C13 1.394(7) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.383(8) . ?
C16 C21 1.392(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.375(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(8) . ?
C22 C27 1.395(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.379(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.394(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.381(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.391(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.399(8) . ?
C28 C33 1.400(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.395(8) . ?
C31 H31 0.9500 . ?
C31 C32 1.382(8) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.396(7) . ?
C34 C39 1.392(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.387(8) . ?
C36 H36 0.9500 . ?
C36 C37 1.387(9) . ?
C37 H37 0.9500 . ?
C37 C38 1.388(8) . ?
C38 H38 0.9500 . ?
C38 C39 1.370(8) . ?
C39 H39 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
C16 Bi1 C2 96.16(19) . . ?
C16 Bi1 C22 93.82(18) . . ?
C22 Bi1 C2 93.60(19) . . ?
C28 Bi2 C12 90.36(19) . . ?
C28 Bi2 C34 93.06(19) . . ?
C34 Bi2 C12 94.8(2) . . ?
C1 O1 C13 116.5(4) . . ?
O1 C1 C2 116.8(5) . . ?
O1 C1 C6 120.4(5) . . ?
C2 C1 C6 122.8(5) . . ?
C1 C2 Bi1 119.9(4) . . ?
C3 C2 Bi1 121.5(4) . . ?
C3 C2 C1 118.6(5) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(5) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(5) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(5) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 119.7(5) . . ?
C5 C6 C1 116.9(5) . . ?
C5 C6 C7 123.4(5) . . ?
C6 C7 C8 107.4(4) . . ?
C6 C7 C14 108.0(4) . . ?
C6 C7 C15 112.0(5) . . ?
C8 C7 C14 108.0(5) . . ?
C8 C7 C15 112.0(5) . . ?
C15 C7 C14 109.2(4) . . ?
C9 C8 C7 123.3(5) . . ?
C13 C8 C7 119.7(5) . . ?
C13 C8 C9 116.9(5) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(5) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(5) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 Bi2 123.2(4) . . ?
C13 C12 Bi2 120.0(4) . . ?
C13 C12 C11 116.7(5) . . ?
O1 C13 C12 115.2(4) . . ?
C8 C13 O1 120.7(4) . . ?
C8 C13 C12 124.1(5) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 . . ?
C17 C16 Bi1 117.7(4) . . ?
C17 C16 C21 119.0(5) . . ?
C21 C16 Bi1 123.0(4) . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.1(5) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(6) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(5) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.1(5) . . ?
C20 C21 H21 120.0 . . ?
C23 C22 Bi1 119.6(4) . . ?
C23 C22 C27 118.3(5) . . ?
C27 C22 Bi1 121.9(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.6(6) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.7(6) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.4(5) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.8(5) . . ?
C27 C26 H26 119.6 . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.2(5) . . ?
C26 C27 H27 119.9 . . ?
C29 C28 Bi2 119.0(4) . . ?
C29 C28 C33 118.0(5) . . ?
C33 C28 Bi2 122.9(4) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 C28 121.3(5) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.7(5) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.8(5) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.4(5) . . ?
C33 C32 H32 119.8 . . ?
C28 C33 H33 119.7 . . ?
C32 C33 C28 120.7(5) . . ?
C32 C33 H33 119.6 . . ?
C35 C34 Bi2 118.7(4) . . ?
C39 C34 Bi2 122.9(4) . . ?
C39 C34 C35 118.4(5) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 C34 120.9(6) . . ?
C36 C35 H35 119.5 . . ?
C35 C36 H36 120.0 . . ?
C35 C36 C37 120.1(5) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 120.7 . . ?
C36 C37 C38 118.7(5) . . ?
C38 C37 H37 120.7 . . ?
C37 C38 H38 119.3 . . ?
C39 C38 C37 121.5(6) . . ?
C39 C38 H38 119.2 . . ?
C34 C39 H39 119.8 . . ?
C38 C39 C34 120.4(5) . . ?
C38 C39 H39 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C2 C3 C4 -177.1(4) . . . . ?
Bi1 C16 C17 C18 171.8(4) . . . . ?
Bi1 C16 C21 C20 -170.8(4) . . . . ?
Bi1 C22 C23 C24 175.8(5) . . . . ?
Bi1 C22 C27 C26 -176.0(4) . . . . ?
Bi2 C12 C13 O1 -4.4(6) . . . . ?
Bi2 C12 C13 C8 175.8(4) . . . . ?
Bi2 C28 C29 C30 -177.0(4) . . . . ?
Bi2 C28 C33 C32 178.1(4) . . . . ?
Bi2 C34 C35 C36 177.6(4) . . . . ?
Bi2 C34 C39 C38 -179.0(4) . . . . ?
O1 C1 C2 Bi1 -2.2(6) . . . . ?
O1 C1 C2 C3 -179.5(4) . . . . ?
O1 C1 C6 C5 178.5(4) . . . . ?
O1 C1 C6 C7 -3.4(7) . . . . ?
C1 O1 C13 C8 27.7(6) . . . . ?
C1 O1 C13 C12 -152.2(4) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
C1 C6 C7 C8 32.2(6) . . . . ?
C1 C6 C7 C14 -84.1(6) . . . . ?
C1 C6 C7 C15 155.6(5) . . . . ?
C2 C1 C6 C5 -2.1(7) . . . . ?
C2 C1 C6 C7 176.0(5) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C3 C4 C5 C6 -0.8(8) . . . . ?
C4 C5 C6 C1 1.9(7) . . . . ?
C4 C5 C6 C7 -176.1(5) . . . . ?
C5 C6 C7 C8 -149.8(5) . . . . ?
C5 C6 C7 C14 93.9(6) . . . . ?
C5 C6 C7 C15 -26.4(7) . . . . ?
C6 C1 C2 Bi1 178.4(4) . . . . ?
C6 C1 C2 C3 1.1(8) . . . . ?
C6 C7 C8 C9 150.6(5) . . . . ?
C6 C7 C8 C13 -33.1(7) . . . . ?
C7 C8 C9 C10 175.4(5) . . . . ?
C7 C8 C13 O1 5.2(7) . . . . ?
C7 C8 C13 C12 -175.0(5) . . . . ?
C8 C9 C10 C11 0.1(8) . . . . ?
C9 C8 C13 O1 -178.3(5) . . . . ?
C9 C8 C13 C12 1.5(8) . . . . ?
C9 C10 C11 C12 0.4(9) . . . . ?
C10 C11 C12 Bi2 -176.6(4) . . . . ?
C10 C11 C12 C13 0.0(8) . . . . ?
C11 C12 C13 O1 178.8(5) . . . . ?
C11 C12 C13 C8 -1.0(8) . . . . ?
C13 O1 C1 C2 152.1(4) . . . . ?
C13 O1 C1 C6 -28.5(6) . . . . ?
C13 C8 C9 C10 -1.0(8) . . . . ?
C14 C7 C8 C9 -93.1(6) . . . . ?
C14 C7 C8 C13 83.2(6) . . . . ?
C15 C7 C8 C9 27.3(7) . . . . ?
C15 C7 C8 C13 -156.5(5) . . . . ?
C16 C17 C18 C19 -0.1(8) . . . . ?
C17 C16 C21 C20 2.1(8) . . . . ?
C17 C18 C19 C20 1.2(8) . . . . ?
C18 C19 C20 C21 -0.5(8) . . . . ?
C19 C20 C21 C16 -1.1(8) . . . . ?
C21 C16 C17 C18 -1.5(8) . . . . ?
C22 C23 C24 C25 -0.9(9) . . . . ?
C23 C22 C27 C26 -1.4(8) . . . . ?
C23 C24 C25 C26 0.9(9) . . . . ?
C24 C25 C26 C27 -1.2(8) . . . . ?
C25 C26 C27 C22 1.5(8) . . . . ?
C27 C22 C23 C24 1.2(9) . . . . ?
C28 C29 C30 C31 -1.2(9) . . . . ?
C29 C28 C33 C32 -0.2(8) . . . . ?
C29 C30 C31 C32 -0.2(8) . . . . ?
C30 C31 C32 C33 1.4(8) . . . . ?
C31 C32 C33 C28 -1.2(8) . . . . ?
C33 C28 C29 C30 1.4(8) . . . . ?
C34 C35 C36 C37 1.3(8) . . . . ?
C35 C34 C39 C38 -1.3(8) . . . . ?
C35 C36 C37 C38 -0.9(8) . . . . ?
C36 C37 C38 C39 -0.7(9) . . . . ?
C37 C38 C39 C34 1.8(9) . . . . ?
C39 C34 C35 C36 -0.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_shelx_SHELXL_version_number     2018/3
####################################################################### 
# 
# 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_13386sadabs
_database_code_depnum_ccdc_archive 'CCDC 2063979'
loop_
_audit_author_name
_audit_author_address
'Nils Noethling'
;Max Planck Institut fuer Kohlenforschung
Germany
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT971_13386sadabs         
;
PROBLEM: Check Calcd Resid. Dens.  0.75A   From Bi1             3.14 eA-3  
RESPONSE:  The high residual electron density could possibly be 
caused by anharmonic displacement of both Bi atoms. 
;
# end Validation Reply Form

_audit_block_code                KUJ-KA-155-01
_audit_creation_date             2020-09-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
(oxybis(2,1-phenylene))bis(dichlorodiphenyl-λ⁵-bismuthane)
;
_chemical_formula_moiety         'C36 H28 Bi2 Cl4 O'
_chemical_formula_sum            'C36 H28 Bi2 Cl4 O'
_chemical_formula_weight         1036.34
_chemical_properties_physical    none
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4334(5)
_cell_length_b                   25.9105(15)
_cell_length_c                   15.5944(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.060(2)
_cell_angle_gamma                90
_cell_volume                     3407.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9797


_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.4417
_cell_measurement_theta_min      2.6960
_shelx_estimated_absorpt_T_max   0.799
_shelx_estimated_absorpt_T_min   0.640
_exptl_absorpt_coefficient_mu    10.658
_exptl_absorpt_correction_T_max  0.85075
_exptl_absorpt_correction_T_min  0.67881

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_exptl_crystal_description       prism
_exptl_crystal_F_000             1944

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0220
-1.00 0.00 0.00 0.0230
0.00 0.00 1.00 0.0100
0.00 0.00 -1.00 0.0100
0.00 1.00 0.00 0.0080
0.00 -1.00 0.00 0.0080
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  dichloromethane, hexane '
_exptl_crystal_size_max          0.046
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.022
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0270
_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       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            151031
_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         30.508
_diffrn_reflns_theta_min         1.524

_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         1\mS
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9085
_reflns_number_total             10382
_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       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'APEX3 (Bruker AXS, 2005-2017)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_refine_diff_density_max         3.134
_refine_diff_density_min         -1.090
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         10382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+5.7737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0542

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.5708 and 0.9067 (SADABS).
INTENSITY STATISTICS FOR DATASET 	
#------------------------------------------------------------------------------- 
Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 2.45     267    267    100.0    20.20    103.09   56.90  0.0462  0.0144
 2.45 - 1.62     616    616    100.0    23.06     72.24   58.09  0.0399  0.0137
 1.62 - 1.28     895    895    100.0    23.17     46.06   51.39  0.0389  0.0146
 1.28 - 1.11     924    924    100.0    22.10     35.78   43.86  0.0466  0.0162
 1.11 - 1.01     877    877    100.0    17.24     26.65   32.97  0.0588  0.0210
 1.01 - 0.93     981    981    100.0    14.04     22.64   27.09  0.0690  0.0262
 0.93 - 0.88     830    830    100.0    12.06     17.49   21.36  0.0862  0.0333
 0.88 - 0.83    1012   1012    100.0    11.32     16.19   18.62  0.0963  0.0377
 0.83 - 0.80     755    755    100.0    10.72     13.84   16.33  0.1110  0.0444
 0.80 - 0.77     834    834    100.0    10.42     13.17   15.62  0.1263  0.0490
 0.77 - 0.74    1021   1021    100.0     9.80     10.77   12.97  0.1454  0.0598
 0.74 - 0.72     768    768    100.0     9.54     10.42   12.18  0.1553  0.0646
 0.72 - 0.70     832    832    100.0     9.15      8.45    9.88  0.1810  0.0805
 0.70 - 0.68     985    985    100.0     8.90      7.63    8.96  0.2039  0.0909
 0.68 - 0.66    1071   1071    100.0     8.51      7.31    8.15  0.2203  0.1012
 0.66 - 0.65     563    563    100.0     8.32      5.96    6.93  0.2573  0.1267
 0.65 - 0.63    1322   1322    100.0     7.90      5.42    6.03  0.2729  0.1441
 0.63 - 0.62     725    725    100.0     7.75      5.22    5.68  0.2990  0.1563
 0.62 - 0.61     750    750    100.0     7.42      4.74    5.04  0.3239  0.1810
 0.61 - 0.60     781    781    100.0     7.17      4.39    4.47  0.3471  0.2085
 0.60 - 0.59     834   1025     81.4     3.23      3.14    2.26  0.4051  0.4727
#-------------------------------------------------------------------------------
 0.69 - 0.59    6537   6728     97.2     7.23      5.43    5.83  0.2715  0.1631
  Inf - 0.59   17643  17834     98.9    11.55     17.54   18.61  0.0711  0.0426
#-------------------------------------------------------------------------------
A resolution cut off (SHEL 99 0.7) was applied to suppress poorly measured 
intensities at higher diffraction angles. The high residual electron density 
(highest peak: 3.13 at 0.78 Å from Bi1 and deepest hole: -1.09 at 
1.28 Å from Bi1) could possibly be caused by anharmonic displacement of 
the Bi atom.

 Highest peak    3.13  at  0.5468  0.2572  0.5539  [  0.78 A from BI1 ]
 Deepest hole   -1.09  at  0.7646  0.9582  0.7596  [  1.28 A from BI2 ]
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C33(H33), C4(H4), C3(H3), C5(H5), C17(H17), C24(H24), C15(H15), C32(H32),
 C34(H34), C18(H18), C36(H36), C16(H16), C9(H9), C14(H14), C35(H35), C23(H23),
 C6(H6), C30(H30), C11(H11), C12(H12), C10(H10), C28(H28), C20(H20), C29(H29),
 C22(H22), C26(H26), C21(H21), C27(H27)
;
_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.59593(2) 0.24872(2) 0.51409(2) 0.01422(3) Uani 1 1 d . . . . .
Bi2 Bi 0.58602(2) 0.45619(2) 0.72305(2) 0.01768(3) Uani 1 1 d . . . . .
Cl2 Cl 0.75158(9) 0.26625(3) 0.37552(5) 0.02170(15) Uani 1 1 d . . . . .
Cl1 Cl 0.45232(9) 0.23740(3) 0.65799(5) 0.01941(14) Uani 1 1 d . . . . .
Cl4 Cl 0.86305(10) 0.49891(3) 0.75288(6) 0.02642(17) Uani 1 1 d . . . . .
Cl3 Cl 0.32374(10) 0.41018(3) 0.68642(5) 0.02247(15) Uani 1 1 d . . . . .
O1 O 0.6763(3) 0.35854(8) 0.60529(15) 0.0202(4) Uani 1 1 d . . . . .
C33 C 0.2233(4) 0.57144(13) 0.7949(2) 0.0256(7) Uani 1 1 d . . . . .
H33 H 0.118106 0.569909 0.815502 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6703(4) 0.45046(12) 0.5915(2) 0.0195(6) Uani 1 1 d . . . . .
C4 C 1.0579(4) 0.30749(13) 0.6860(2) 0.0214(6) Uani 1 1 d . . . . .
H4 H 1.149175 0.318472 0.717621 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3947(4) 0.29155(12) 0.4574(2) 0.0176(6) Uani 1 1 d . . . . .
C2 C 0.8057(3) 0.32585(11) 0.62080(19) 0.0165(6) Uani 1 1 d . . . . .
C1 C 0.7981(3) 0.27585(11) 0.59119(19) 0.0144(5) Uani 1 1 d . . . . .
C3 C 0.9376(4) 0.34251(13) 0.6681(2) 0.0220(6) Uani 1 1 d . . . . .
H3 H 0.945059 0.377166 0.687649 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6151(4) 0.16469(12) 0.4948(2) 0.0223(6) Uani 1 1 d . . . . .
C5 C 1.0473(4) 0.25681(12) 0.6587(2) 0.0230(7) Uani 1 1 d . . . . .
H5 H 1.129469 0.233103 0.673037 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2210(4) 0.30580(15) 0.3377(2) 0.0298(8) Uani 1 1 d . . . . .
H17 H 0.186352 0.297849 0.280938 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7102(4) 0.40279(12) 0.5580(2) 0.0198(6) Uani 1 1 d . . . . .
C24 C 0.6306(4) 0.13246(13) 0.5659(2) 0.0265(7) Uani 1 1 d . . . . .
H24 H 0.630884 0.146098 0.622436 0.032 Uiso 1 1 calc R U . . .
C15 C 0.1910(4) 0.35435(14) 0.4672(2) 0.0296(8) Uani 1 1 d . . . . .
H15 H 0.137716 0.380504 0.498204 0.035 Uiso 1 1 calc R U . . .
C32 C 0.3063(4) 0.52607(12) 0.7799(2) 0.0238(7) Uani 1 1 d . . . . .
H32 H 0.257893 0.493479 0.789084 0.029 Uiso 1 1 calc R U . . .
C34 C 0.2932(4) 0.61870(13) 0.7801(2) 0.0279(7) Uani 1 1 d . . . . .
H34 H 0.235585 0.649602 0.789816 0.033 Uiso 1 1 calc R U . . .
C31 C 0.4600(4) 0.52901(11) 0.7514(2) 0.0192(6) Uani 1 1 d . . . . .
C18 C 0.3503(4) 0.27990(14) 0.3737(2) 0.0246(7) Uani 1 1 d . . . . .
H18 H 0.406691 0.254907 0.341709 0.030 Uiso 1 1 calc R U . . .
C36 C 0.5335(5) 0.57607(13) 0.7374(2) 0.0278(7) Uani 1 1 d . . . . .
H36 H 0.640094 0.577641 0.718939 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1428(4) 0.34290(15) 0.3839(2) 0.0295(8) Uani 1 1 d . . . . .
H16 H 0.055453 0.360743 0.358567 0.035 Uiso 1 1 calc R U . . .
C25 C 0.6267(4) 0.40275(13) 0.8313(2) 0.0238(7) Uani 1 1 d . . . . .
C9 C 0.7800(4) 0.39957(13) 0.4785(2) 0.0268(7) Uani 1 1 d . . . . .
H9 H 0.805741 0.366933 0.454751 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3171(4) 0.32782(13) 0.5060(2) 0.0233(7) Uani 1 1 d . . . . .
H14 H 0.348369 0.334466 0.563772 0.028 Uiso 1 1 calc R U . . .
C35 C 0.4466(5) 0.62108(13) 0.7513(3) 0.0320(8) Uani 1 1 d . . . . .
H35 H 0.493744 0.653719 0.740708 0.038 Uiso 1 1 calc R U . . .
C23 C 0.6456(6) 0.07963(14) 0.5516(3) 0.0378(10) Uani 1 1 d . . . . .
H23 H 0.659344 0.056850 0.598916 0.045 Uiso 1 1 calc R U . . .
C6 C 0.9174(4) 0.24056(12) 0.6105(2) 0.0199(6) Uani 1 1 d . . . . .
H6 H 0.909938 0.205899 0.591024 0.024 Uiso 1 1 calc R U . . .
C30 C 0.5715(4) 0.35285(13) 0.8277(3) 0.0286(8) Uani 1 1 d . . . . .
H30 H 0.520611 0.339716 0.777363 0.034 Uiso 1 1 calc R U . . .
C11 C 0.7717(5) 0.49214(15) 0.4672(2) 0.0361(9) Uani 1 1 d . . . . .
H11 H 0.794150 0.522669 0.435966 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6991(5) 0.49535(13) 0.5457(2) 0.0300(8) Uani 1 1 d . . . . .
H12 H 0.669230 0.527938 0.568214 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8117(5) 0.44452(15) 0.4342(2) 0.0334(8) Uani 1 1 d . . . . .
H10 H 0.861727 0.442617 0.380172 0.040 Uiso 1 1 calc R U . . .
C28 C 0.6675(5) 0.34117(18) 0.9728(3) 0.0413(10) Uani 1 1 d . . . . .
H28 H 0.682951 0.319606 1.021469 0.050 Uiso 1 1 calc R U . . .
C20 C 0.6118(6) 0.14585(14) 0.4118(2) 0.0370(9) Uani 1 1 d . . . . .
H20 H 0.602679 0.168669 0.364314 0.044 Uiso 1 1 calc R U . . .
C29 C 0.5931(4) 0.32203(15) 0.9010(3) 0.0348(9) Uani 1 1 d . . . . .
H29 H 0.555661 0.287453 0.900636 0.042 Uiso 1 1 calc R U . . .
C22 C 0.6405(6) 0.06010(14) 0.4690(3) 0.0456(12) Uani 1 1 d . . . . .
H22 H 0.649740 0.023964 0.460041 0.055 Uiso 1 1 calc R U . . .
C26 C 0.7012(6) 0.42308(17) 0.9037(2) 0.0401(10) Uani 1 1 d . . . . .
H26 H 0.738456 0.457683 0.904447 0.048 Uiso 1 1 calc R U . . .
C21 C 0.6221(7) 0.09279(16) 0.3993(3) 0.0485(12) Uani 1 1 d . . . . .
H21 H 0.616461 0.078987 0.342887 0.058 Uiso 1 1 calc R U . . .
C27 C 0.7200(6) 0.39137(19) 0.9751(3) 0.0503(12) Uani 1 1 d . . . . .
H27 H 0.769504 0.404494 1.025751 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl2 2.5892(8) . ?
Bi1 Cl1 2.5862(8) . ?
Bi1 C13 2.199(3) . ?
Bi1 C1 2.184(3) . ?
Bi1 C19 2.204(3) . ?
Bi2 Cl4 2.6191(8) . ?
Bi2 Cl3 2.5677(8) . ?
Bi2 C7 2.189(3) . ?
Bi2 C31 2.214(3) . ?
Bi2 C25 2.205(3) . ?
O1 C2 1.399(4) . ?
O1 C8 1.396(4) . ?
C33 H33 0.9500 . ?
C33 C32 1.391(5) . ?
C33 C34 1.380(5) . ?
C7 C8 1.385(4) . ?
C7 C12 1.388(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.386(5) . ?
C4 C5 1.383(5) . ?
C13 C18 1.385(4) . ?
C13 C14 1.380(4) . ?
C2 C1 1.377(4) . ?
C2 C3 1.392(4) . ?
C1 C6 1.389(4) . ?
C3 H3 0.9500 . ?
C19 C24 1.392(4) . ?
C19 C20 1.382(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(5) . ?
C17 C16 1.377(5) . ?
C8 C9 1.384(5) . ?
C24 H24 0.9500 . ?
C24 C23 1.393(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(5) . ?
C15 C14 1.394(5) . ?
C32 H32 0.9500 . ?
C32 C31 1.380(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.379(5) . ?
C31 C36 1.387(4) . ?
C18 H18 0.9500 . ?
C36 H36 0.9500 . ?
C36 C35 1.396(5) . ?
C16 H16 0.9500 . ?
C25 C30 1.375(5) . ?
C25 C26 1.385(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(5) . ?
C14 H14 0.9500 . ?
C35 H35 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.384(6) . ?
C6 H6 0.9500 . ?
C30 H30 0.9500 . ?
C30 C29 1.404(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(6) . ?
C11 C10 1.381(6) . ?
C12 H12 0.9500 . ?
C10 H10 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.366(6) . ?
C28 C27 1.375(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(5) . ?
C29 H29 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.384(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.390(6) . ?
C21 H21 0.9500 . ?
C27 H27 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
Cl1 Bi1 Cl2 175.42(3) . . ?
C13 Bi1 Cl2 88.59(8) . . ?
C13 Bi1 Cl1 92.04(8) . . ?
C13 Bi1 C19 120.09(12) . . ?
C1 Bi1 Cl2 90.01(8) . . ?
C1 Bi1 Cl1 86.12(8) . . ?
C1 Bi1 C13 130.36(11) . . ?
C1 Bi1 C19 109.56(12) . . ?
C19 Bi1 Cl2 91.13(9) . . ?
C19 Bi1 Cl1 92.47(9) . . ?
Cl3 Bi2 Cl4 176.06(3) . . ?
C7 Bi2 Cl4 83.75(9) . . ?
C7 Bi2 Cl3 93.06(9) . . ?
C7 Bi2 C31 114.23(12) . . ?
C7 Bi2 C25 128.79(12) . . ?
C31 Bi2 Cl4 91.96(9) . . ?
C31 Bi2 Cl3 91.45(8) . . ?
C25 Bi2 Cl4 90.22(9) . . ?
C25 Bi2 Cl3 89.99(9) . . ?
C25 Bi2 C31 116.77(12) . . ?
C8 O1 C2 115.0(2) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C34 C33 C32 120.3(3) . . ?
C8 C7 Bi2 120.0(2) . . ?
C8 C7 C12 120.5(3) . . ?
C12 C7 Bi2 119.2(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.1(3) . . ?
C18 C13 Bi1 117.5(2) . . ?
C14 C13 Bi1 119.6(2) . . ?
C14 C13 C18 122.9(3) . . ?
C1 C2 O1 118.7(3) . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 O1 121.1(3) . . ?
C2 C1 Bi1 121.2(2) . . ?
C2 C1 C6 121.2(3) . . ?
C6 C1 Bi1 117.6(2) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C24 C19 Bi1 119.3(2) . . ?
C20 C19 Bi1 118.5(2) . . ?
C20 C19 C24 122.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C7 C8 O1 118.7(3) . . ?
C9 C8 O1 121.2(3) . . ?
C9 C8 C7 120.1(3) . . ?
C19 C24 H24 121.0 . . ?
C19 C24 C23 118.0(3) . . ?
C23 C24 H24 121.0 . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C33 C32 H32 120.4 . . ?
C31 C32 C33 119.1(3) . . ?
C31 C32 H32 120.4 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0(3) . . ?
C35 C34 H34 120.0 . . ?
C32 C31 Bi2 118.3(2) . . ?
C32 C31 C36 121.6(3) . . ?
C36 C31 Bi2 120.0(2) . . ?
C13 C18 C17 118.1(3) . . ?
C13 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C31 C36 H36 120.9 . . ?
C31 C36 C35 118.2(3) . . ?
C35 C36 H36 120.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C30 C25 Bi2 120.7(3) . . ?
C30 C25 C26 122.7(3) . . ?
C26 C25 Bi2 116.5(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.5 . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C34 C35 C36 120.7(3) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C25 C30 H30 121.2 . . ?
C25 C30 C29 117.5(4) . . ?
C29 C30 H30 121.2 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.3(3) . . ?
C11 C12 H12 120.4 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C29 C28 H28 119.7 . . ?
C29 C28 C27 120.5(4) . . ?
C27 C28 H28 119.7 . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.7(4) . . ?
C21 C20 H20 120.7 . . ?
C30 C29 H29 119.6 . . ?
C28 C29 C30 120.8(4) . . ?
C28 C29 H29 119.6 . . ?
C23 C22 H22 119.7 . . ?
C21 C22 C23 120.5(4) . . ?
C21 C22 H22 119.7 . . ?
C25 C26 H26 121.0 . . ?
C25 C26 C27 118.1(4) . . ?
C27 C26 H26 121.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(4) . . ?
C22 C21 H21 120.0 . . ?
C28 C27 C26 120.4(4) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C13 C18 C17 178.5(3) . . . . ?
Bi1 C13 C14 C15 179.5(3) . . . . ?
Bi1 C1 C6 C5 179.5(2) . . . . ?
Bi1 C19 C24 C23 -178.7(3) . . . . ?
Bi1 C19 C20 C21 -179.3(4) . . . . ?
Bi2 C7 C8 O1 8.1(4) . . . . ?
Bi2 C7 C8 C9 -172.8(2) . . . . ?
Bi2 C7 C12 C11 171.6(3) . . . . ?
Bi2 C31 C36 C35 176.3(3) . . . . ?
Bi2 C25 C30 C29 -176.1(3) . . . . ?
Bi2 C25 C26 C27 176.1(4) . . . . ?
O1 C2 C1 Bi1 4.0(4) . . . . ?
O1 C2 C1 C6 -174.8(3) . . . . ?
O1 C2 C3 C4 176.0(3) . . . . ?
O1 C8 C9 C10 -179.8(3) . . . . ?
C33 C32 C31 Bi2 -177.6(3) . . . . ?
C33 C32 C31 C36 0.0(5) . . . . ?
C33 C34 C35 C36 -0.6(6) . . . . ?
C7 C8 C9 C10 1.2(5) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C2 O1 C8 C7 -125.9(3) . . . . ?
C2 O1 C8 C9 55.1(4) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C3 C4 C5 C6 1.9(5) . . . . ?
C3 C2 C1 Bi1 -178.5(2) . . . . ?
C3 C2 C1 C6 2.7(5) . . . . ?
C19 C24 C23 C22 -1.8(6) . . . . ?
C19 C20 C21 C22 -2.1(8) . . . . ?
C5 C4 C3 C2 -0.8(5) . . . . ?
C8 O1 C2 C1 -120.3(3) . . . . ?
C8 O1 C2 C3 62.2(4) . . . . ?
C8 C7 C12 C11 -1.6(6) . . . . ?
C8 C9 C10 C11 -1.4(6) . . . . ?
C24 C19 C20 C21 0.9(7) . . . . ?
C24 C23 C22 C21 0.7(8) . . . . ?
C32 C33 C34 C35 -0.8(6) . . . . ?
C32 C31 C36 C35 -1.3(5) . . . . ?
C34 C33 C32 C31 1.1(5) . . . . ?
C31 C36 C35 C34 1.6(6) . . . . ?
C18 C13 C14 C15 -1.5(5) . . . . ?
C18 C17 C16 C15 -0.8(6) . . . . ?
C16 C17 C18 C13 1.7(5) . . . . ?
C16 C15 C14 C13 2.4(5) . . . . ?
C25 C30 C29 C28 -0.5(6) . . . . ?
C25 C26 C27 C28 0.8(7) . . . . ?
C14 C13 C18 C17 -0.5(5) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C23 C22 C21 C20 1.3(8) . . . . ?
C30 C25 C26 C27 -0.1(7) . . . . ?
C12 C7 C8 O1 -178.8(3) . . . . ?
C12 C7 C8 C9 0.3(5) . . . . ?
C12 C11 C10 C9 0.1(6) . . . . ?
C10 C11 C12 C7 1.4(6) . . . . ?
C20 C19 C24 C23 1.0(6) . . . . ?
C29 C28 C27 C26 -1.4(8) . . . . ?
C26 C25 C30 C29 -0.1(6) . . . . ?
C27 C28 C29 C30 1.2(7) . . . . ?

