# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1541504'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H72 Bi4 O10 S8'
_chemical_formula_sum            'C56 H72 Bi4 O10 S8'
_chemical_formula_weight         1997.53

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3241(5)
_cell_length_b                   12.9973(8)
_cell_length_c                   14.0496(8)
_cell_angle_alpha                114.879(6)
_cell_angle_beta                 101.803(5)
_cell_angle_gamma                99.558(5)
_cell_volume                     1605.25(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    8092
_cell_measurement_theta_min      2.9608
_cell_measurement_theta_max      28.5194

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.066
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    11.242
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Gemini S'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12911
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.971
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6199
_reflns_number_gt                4863
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6199
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2711(6) 0.1163(6) 0.4095(6) 0.0215(15) Uani 1 1 d . . . . .
C2 C 0.2952(7) 0.0831(7) 0.2996(6) 0.0312(18) Uani 1 1 d . . . . .
H2A H 0.3914 0.1138 0.3107 0.047 Uiso 1 1 calc R U . . .
H2B H 0.2681 -0.0015 0.2566 0.047 Uiso 1 1 calc R U . . .
H2C H 0.2416 0.1156 0.2613 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3517(7) 0.0612(7) 0.4694(7) 0.0352(19) Uani 1 1 d . . . . .
H3A H 0.4488 0.0938 0.4855 0.053 Uiso 1 1 calc R U . . .
H3B H 0.3305 0.0780 0.5369 0.053 Uiso 1 1 calc R U . . .
H3C H 0.3264 -0.0229 0.4235 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3093(7) 0.2482(6) 0.4824(6) 0.0249(16) Uani 1 1 d . . . . .
C5 C 0.3290(7) 0.3092(7) 0.5941(6) 0.0337(19) Uani 1 1 d . . . . .
H5 H 0.3268 0.2746 0.6400 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3537(9) 0.4349(7) 0.6299(8) 0.047(3) Uani 1 1 d . . . . .
H6 H 0.3674 0.4899 0.7025 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3552(10) 0.4650(7) 0.5515(9) 0.056(3) Uani 1 1 d . . . . .
H7 H 0.3713 0.5422 0.5623 0.068 Uiso 1 1 calc R U . . .
C8 C -0.1690(7) 0.2115(6) 0.3218(5) 0.0216(15) Uani 1 1 d . . . . .
C9 C -0.0700(7) 0.3318(6) 0.4124(6) 0.0312(18) Uani 1 1 d . . . . .
H9A H -0.0924 0.3937 0.3981 0.047 Uiso 1 1 calc R U . . .
H9B H -0.0792 0.3442 0.4828 0.047 Uiso 1 1 calc R U . . .
H9C H 0.0232 0.3324 0.4129 0.047 Uiso 1 1 calc R U . . .
C10 C -0.3176(7) 0.2125(6) 0.3220(6) 0.0247(16) Uani 1 1 d . . . . .
H10A H -0.3383 0.2758 0.3093 0.037 Uiso 1 1 calc R U . . .
H10B H -0.3805 0.1385 0.2648 0.037 Uiso 1 1 calc R U . . .
H10C H -0.3268 0.2238 0.3921 0.037 Uiso 1 1 calc R U . . .
C11 C -0.1547(6) 0.1929(6) 0.2103(5) 0.0207(15) Uani 1 1 d . . . . .
C12 C -0.2246(7) 0.2226(6) 0.1369(6) 0.0291(17) Uani 1 1 d . . . . .
H12 H -0.2966 0.2566 0.1463 0.035 Uiso 1 1 calc R U . . .
C13 C -0.1760(8) 0.1964(7) 0.0451(7) 0.040(2) Uani 1 1 d . . . . .
H13 H -0.2131 0.2102 -0.0131 0.048 Uiso 1 1 calc R U . . .
C14 C -0.0689(9) 0.1487(7) 0.0507(6) 0.038(2) Uani 1 1 d . . . . .
H14 H -0.0236 0.1270 -0.0024 0.045 Uiso 1 1 calc R U . . .
C15 C -0.4469(6) -0.2222(6) 0.1463(6) 0.0224(16) Uani 1 1 d . . . . .
C16 C -0.5535(7) -0.3405(6) 0.1073(6) 0.036(2) Uani 1 1 d . . . . .
H16A H -0.6398 -0.3430 0.0635 0.054 Uiso 1 1 calc R U . . .
H16B H -0.5212 -0.4044 0.0638 0.054 Uiso 1 1 calc R U . . .
H16C H -0.5662 -0.3480 0.1701 0.054 Uiso 1 1 calc R U . . .
C17 C -0.4957(8) -0.1209(7) 0.2202(6) 0.0346(19) Uani 1 1 d . . . . .
H17A H -0.5789 -0.1177 0.1774 0.052 Uiso 1 1 calc R U . . .
H17B H -0.5133 -0.1341 0.2792 0.052 Uiso 1 1 calc R U . . .
H17C H -0.4255 -0.0474 0.2501 0.052 Uiso 1 1 calc R U . . .
C18 C -0.4213(6) -0.2060(6) 0.0512(5) 0.0230(16) Uani 1 1 d . . . . .
C19 C -0.4012(7) -0.1068(7) 0.0383(6) 0.0285(17) Uani 1 1 d . . . . .
H19 H -0.4100 -0.0354 0.0879 0.034 Uiso 1 1 calc R U . . .
C20 C -0.3657(8) -0.1235(8) -0.0580(7) 0.042(2) Uani 1 1 d . . . . .
H20 H -0.3505 -0.0644 -0.0787 0.051 Uiso 1 1 calc R U . . .
C21 C -0.3560(9) -0.2313(8) -0.1163(7) 0.048(2) Uani 1 1 d . . . . .
H21 H -0.3325 -0.2561 -0.1813 0.058 Uiso 1 1 calc R U . . .
C22 C -0.0292(7) -0.3429(6) 0.1945(6) 0.0256(16) Uani 1 1 d . . . . .
C23 C -0.1633(9) -0.4345(7) 0.1457(9) 0.072(4) Uani 1 1 d . . . . .
H23A H -0.1554 -0.5069 0.0913 0.108 Uiso 1 1 calc R U . . .
H23B H -0.1894 -0.4474 0.2025 0.108 Uiso 1 1 calc R U . . .
H23C H -0.2322 -0.4088 0.1116 0.108 Uiso 1 1 calc R U . . .
C24 C 0.0133(12) -0.3222(10) 0.1044(8) 0.071(4) Uani 1 1 d . . . . .
H24A H 0.0183 -0.3952 0.0488 0.106 Uiso 1 1 calc R U . . .
H24B H -0.0536 -0.2937 0.0719 0.106 Uiso 1 1 calc R U . . .
H24C H 0.1021 -0.2647 0.1361 0.106 Uiso 1 1 calc R U . . .
C25 C 0.0826(7) -0.3803(6) 0.2485(5) 0.0216(15) Uani 1 1 d . . . . .
C26 C 0.0938(10) -0.4894(7) 0.2266(8) 0.058(3) Uani 1 1 d . . . . .
H26 H 0.0257 -0.5585 0.1743 0.069 Uiso 1 1 calc R U . . .
C27 C 0.2176(13) -0.4883(9) 0.2902(9) 0.083(4) Uani 1 1 d . . . . .
H27 H 0.2396 -0.5569 0.2841 0.099 Uiso 1 1 calc R U . . .
C28 C 0.3021(10) -0.3796(9) 0.3607(8) 0.057(3) Uani 1 1 d . . . . .
H28 H 0.3881 -0.3633 0.4091 0.069 Uiso 1 1 calc R U . . .
O1 O 0.1259(4) 0.0672(4) 0.3856(3) 0.0224(11) Uani 1 1 d . . . . .
O2 O -0.1384(4) 0.1174(4) 0.3407(4) 0.0177(10) Uani 1 1 d . . . . .
O3 O -0.1076(4) -0.0417(4) 0.4091(3) 0.0151(9) Uani 1 1 d . . . . .
O4 O -0.3222(4) -0.2267(4) 0.2106(4) 0.0228(11) Uani 1 1 d . . . . .
O5 O -0.0358(5) -0.2333(4) 0.2761(4) 0.0227(11) Uani 1 1 d . . . . .
S1 S 0.3241(2) 0.34404(17) 0.42803(19) 0.0419(5) Uani 1 1 d . . . . .
S2 S -0.0281(2) 0.13374(19) 0.16626(16) 0.0353(5) Uani 1 1 d . . . . .
S3 S -0.3922(3) -0.3193(2) -0.05656(18) 0.0524(6) Uani 1 1 d . . . . .
S4 S 0.2290(2) -0.27569(18) 0.34894(18) 0.0386(5) Uani 1 1 d . . . . .
Bi1 Bi 0.00697(2) 0.13663(2) 0.49042(2) 0.01570(8) Uani 1 1 d . . . . .
Bi2 Bi -0.13005(2) -0.11409(2) 0.24169(2) 0.01688(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.437(7) . ?
C1 C2 1.505(10) . ?
C1 C4 1.509(9) . ?
C1 C3 1.527(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.379(10) . ?
C4 S1 1.715(8) . ?
C5 C6 1.452(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.316(15) . ?
C6 H6 0.9300 . ?
C7 S1 1.701(9) . ?
C7 H7 0.9300 . ?
C8 O2 1.426(8) . ?
C8 C11 1.524(10) . ?
C8 C10 1.537(9) . ?
C8 C9 1.540(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.363(10) . ?
C11 S2 1.716(6) . ?
C12 C13 1.408(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(11) . ?
C13 H13 0.9300 . ?
C14 S2 1.692(9) . ?
C14 H14 0.9300 . ?
C15 O4 1.439(8) . ?
C15 C18 1.504(10) . ?
C15 C17 1.533(9) . ?
C15 C16 1.535(10) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.364(11) . ?
C18 S3 1.735(7) . ?
C19 C20 1.412(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.326(11) . ?
C20 H20 0.9300 . ?
C21 S3 1.716(10) . ?
C21 H21 0.9300 . ?
C22 O5 1.428(7) . ?
C22 C23 1.477(11) . ?
C22 C25 1.511(9) . ?
C22 C24 1.531(12) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.349(11) . ?
C25 S4 1.719(7) . ?
C26 C27 1.396(13) . ?
C26 H26 0.9300 . ?
C27 C28 1.341(14) . ?
C27 H27 0.9300 . ?
C28 S4 1.701(10) . ?
C28 H28 0.9300 . ?
O1 Bi1 2.117(4) . ?
O2 Bi1 2.209(4) . ?
O2 Bi2 2.759(4) . ?
O3 Bi2 2.077(4) . ?
O3 Bi1 2.095(4) . ?
O3 Bi1 2.426(4) 2_556 ?
O4 Bi2 2.101(4) . ?
O5 Bi2 2.126(5) . ?
Bi1 O3 2.426(4) 2_556 ?
Bi1 Bi2 3.4201(5) . ?
Bi1 Bi1 3.6548(5) 2_556 ?

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
O1 C1 C2 105.9(5) . . ?
O1 C1 C4 108.9(5) . . ?
C2 C1 C4 113.2(6) . . ?
O1 C1 C3 109.2(6) . . ?
C2 C1 C3 110.0(6) . . ?
C4 C1 C3 109.5(6) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C1 128.4(7) . . ?
C5 C4 S1 110.5(5) . . ?
C1 C4 S1 121.0(6) . . ?
C4 C5 C6 110.4(8) . . ?
C4 C5 H5 124.8 . . ?
C6 C5 H5 124.8 . . ?
C7 C6 C5 114.7(8) . . ?
C7 C6 H6 122.6 . . ?
C5 C6 H6 122.6 . . ?
C6 C7 S1 111.1(7) . . ?
C6 C7 H7 124.4 . . ?
S1 C7 H7 124.4 . . ?
O2 C8 C11 109.3(5) . . ?
O2 C8 C10 109.4(6) . . ?
C11 C8 C10 109.4(5) . . ?
O2 C8 C9 110.9(6) . . ?
C11 C8 C9 109.2(6) . . ?
C10 C8 C9 108.6(5) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 129.7(6) . . ?
C12 C11 S2 110.7(6) . . ?
C8 C11 S2 119.5(5) . . ?
C11 C12 C13 112.7(7) . . ?
C11 C12 H12 123.6 . . ?
C13 C12 H12 123.6 . . ?
C14 C13 C12 112.6(8) . . ?
C14 C13 H13 123.7 . . ?
C12 C13 H13 123.7 . . ?
C13 C14 S2 111.7(6) . . ?
C13 C14 H14 124.1 . . ?
S2 C14 H14 124.1 . . ?
O4 C15 C18 109.8(5) . . ?
O4 C15 C17 109.3(5) . . ?
C18 C15 C17 111.0(6) . . ?
O4 C15 C16 105.4(6) . . ?
C18 C15 C16 111.9(6) . . ?
C17 C15 C16 109.2(6) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C15 129.8(6) . . ?
C19 C18 S3 109.5(6) . . ?
C15 C18 S3 120.3(5) . . ?
C18 C19 C20 113.2(7) . . ?
C18 C19 H19 123.4 . . ?
C20 C19 H19 123.4 . . ?
C21 C20 C19 113.8(9) . . ?
C21 C20 H20 123.1 . . ?
C19 C20 H20 123.1 . . ?
C20 C21 S3 111.4(7) . . ?
C20 C21 H21 124.3 . . ?
S3 C21 H21 124.3 . . ?
O5 C22 C23 111.6(6) . . ?
O5 C22 C25 107.8(5) . . ?
C23 C22 C25 111.2(7) . . ?
O5 C22 C24 108.4(6) . . ?
C23 C22 C24 109.8(8) . . ?
C25 C22 C24 108.0(6) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C22 130.2(7) . . ?
C26 C25 S4 109.6(6) . . ?
C22 C25 S4 120.1(5) . . ?
C25 C26 C27 113.4(8) . . ?
C25 C26 H26 123.3 . . ?
C27 C26 H26 123.3 . . ?
C28 C27 C26 114.0(8) . . ?
C28 C27 H27 123.0 . . ?
C26 C27 H27 123.0 . . ?
C27 C28 S4 110.1(7) . . ?
C27 C28 H28 124.9 . . ?
S4 C28 H28 124.9 . . ?
C1 O1 Bi1 125.2(3) . . ?
C8 O2 Bi1 126.1(4) . . ?
C8 O2 Bi2 144.9(4) . . ?
Bi1 O2 Bi2 86.27(13) . . ?
Bi2 O3 Bi1 110.2(2) . . ?
Bi2 O3 Bi1 118.22(17) . 2_556 ?
Bi1 O3 Bi1 107.68(16) . 2_556 ?
C15 O4 Bi2 120.7(4) . . ?
C22 O5 Bi2 124.8(4) . . ?
C7 S1 C4 93.3(5) . . ?
C14 S2 C11 92.2(4) . . ?
C21 S3 C18 92.1(4) . . ?
C28 S4 C25 92.8(4) . . ?
O3 Bi1 O1 81.19(16) . . ?
O3 Bi1 O2 76.25(16) . . ?
O1 Bi1 O2 84.75(17) . . ?
O3 Bi1 O3 72.32(16) . 2_556 ?
O1 Bi1 O3 85.00(17) . 2_556 ?
O2 Bi1 O3 148.06(14) . 2_556 ?
O3 Bi1 Bi2 34.75(12) . . ?
O1 Bi1 Bi2 57.32(11) . . ?
O2 Bi1 Bi2 53.60(10) . . ?
O3 Bi1 Bi2 95.80(9) 2_556 . ?
O3 Bi1 Bi1 39.22(12) . 2_556 ?
O1 Bi1 Bi1 81.63(14) . 2_556 ?
O2 Bi1 Bi1 115.28(11) . 2_556 ?
O3 Bi1 Bi1 33.09(9) 2_556 2_556 ?
Bi2 Bi1 Bi1 66.188(9) . 2_556 ?
O3 Bi2 O4 88.69(17) . . ?
O3 Bi2 O5 81.34(16) . . ?
O4 Bi2 O5 88.10(18) . . ?
O3 Bi2 O2 64.93(15) . . ?
O4 Bi2 O2 109.16(15) . . ?
O5 Bi2 O2 140.95(14) . . ?
O3 Bi2 Bi1 35.09(12) . . ?
O4 Bi2 Bi1 118.15(12) . . ?
O5 Bi2 Bi1 100.82(11) . . ?
O2 Bi2 Bi1 40.13(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
O1 C1 C4 C5 77.8(9) . . . . ?
C2 C1 C4 C5 -164.7(7) . . . . ?
C3 C1 C4 C5 -41.5(9) . . . . ?
O1 C1 C4 S1 -98.1(6) . . . . ?
C2 C1 C4 S1 19.4(8) . . . . ?
C3 C1 C4 S1 142.5(6) . . . . ?
C1 C4 C5 C6 -175.4(7) . . . . ?
S1 C4 C5 C6 0.9(8) . . . . ?
C4 C5 C6 C7 -1.3(11) . . . . ?
C5 C6 C7 S1 1.1(11) . . . . ?
O2 C8 C11 C12 148.2(7) . . . . ?
C10 C8 C11 C12 28.4(10) . . . . ?
C9 C8 C11 C12 -90.4(8) . . . . ?
O2 C8 C11 S2 -35.9(7) . . . . ?
C10 C8 C11 S2 -155.7(5) . . . . ?
C9 C8 C11 S2 85.5(6) . . . . ?
C8 C11 C12 C13 176.7(7) . . . . ?
S2 C11 C12 C13 0.5(8) . . . . ?
C11 C12 C13 C14 -0.8(10) . . . . ?
C12 C13 C14 S2 0.8(9) . . . . ?
O4 C15 C18 C19 -102.4(8) . . . . ?
C17 C15 C18 C19 18.5(9) . . . . ?
C16 C15 C18 C19 140.9(7) . . . . ?
O4 C15 C18 S3 69.4(6) . . . . ?
C17 C15 C18 S3 -169.6(5) . . . . ?
C16 C15 C18 S3 -47.3(7) . . . . ?
C15 C18 C19 C20 173.7(7) . . . . ?
S3 C18 C19 C20 1.1(8) . . . . ?
C18 C19 C20 C21 -1.3(10) . . . . ?
C19 C20 C21 S3 0.7(10) . . . . ?
O5 C22 C25 C26 149.5(9) . . . . ?
C23 C22 C25 C26 26.9(13) . . . . ?
C24 C22 C25 C26 -93.6(11) . . . . ?
O5 C22 C25 S4 -35.3(8) . . . . ?
C23 C22 C25 S4 -157.9(6) . . . . ?
C24 C22 C25 S4 81.7(7) . . . . ?
C22 C25 C26 C27 176.1(10) . . . . ?
S4 C25 C26 C27 0.4(13) . . . . ?
C25 C26 C27 C28 -0.1(17) . . . . ?
C26 C27 C28 S4 -0.2(15) . . . . ?
C2 C1 O1 Bi1 -151.6(5) . . . . ?
C4 C1 O1 Bi1 -29.5(8) . . . . ?
C3 C1 O1 Bi1 90.0(6) . . . . ?
C11 C8 O2 Bi1 129.3(4) . . . . ?
C10 C8 O2 Bi1 -110.9(5) . . . . ?
C9 C8 O2 Bi1 9.0(8) . . . . ?
C11 C8 O2 Bi2 -24.4(9) . . . . ?
C10 C8 O2 Bi2 95.4(7) . . . . ?
C9 C8 O2 Bi2 -144.8(5) . . . . ?
C18 C15 O4 Bi2 39.8(6) . . . . ?
C17 C15 O4 Bi2 -82.2(6) . . . . ?
C16 C15 O4 Bi2 160.5(4) . . . . ?
C23 C22 O5 Bi2 -75.8(8) . . . . ?
C25 C22 O5 Bi2 161.8(4) . . . . ?
C24 C22 O5 Bi2 45.1(8) . . . . ?
C6 C7 S1 C4 -0.4(8) . . . . ?
C5 C4 S1 C7 -0.3(6) . . . . ?
C1 C4 S1 C7 176.3(6) . . . . ?
C13 C14 S2 C11 -0.4(6) . . . . ?
C12 C11 S2 C14 0.0(6) . . . . ?
C8 C11 S2 C14 -176.7(6) . . . . ?
C20 C21 S3 C18 -0.1(7) . . . . ?
C19 C18 S3 C21 -0.6(6) . . . . ?
C15 C18 S3 C21 -174.0(6) . . . . ?
C27 C28 S4 C25 0.4(10) . . . . ?
C26 C25 S4 C28 -0.5(8) . . . . ?
C22 C25 S4 C28 -176.6(6) . . . . ?

_refine_diff_density_max         2.278
_refine_diff_density_min         -1.531
_refine_diff_density_rms         0.207

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1541506'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 Bi O3 S3'
_chemical_formula_sum            'C21 H27 Bi O3 S3'
_chemical_formula_weight         632.58

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.8317(7)
_cell_length_b                   18.9174(5)
_cell_length_c                   11.7510(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4630.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    110
_cell_measurement_reflns_used    6576
_cell_measurement_theta_min      2.9243
_cell_measurement_theta_max      28.5967

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_F_000             2464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    7.904
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.33399
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13648
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.932
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4019
_reflns_number_gt                2996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4019
_refine_ls_number_parameters     260
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0416
_refine_ls_wR_factor_gt          0.0401
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.70835(18) 0.11041(19) 0.0443(3) 0.0236(10) Uani 1 1 d . . . . .
C2 C 0.7581(2) 0.1354(2) -0.0417(3) 0.0387(11) Uani 1 1 d . . . . .
H2A H 0.7367 0.1559 -0.1061 0.058 Uiso 1 1 calc R U . . .
H2B H 0.7835 0.0959 -0.0663 0.058 Uiso 1 1 calc R U . . .
H2C H 0.7854 0.1701 -0.0070 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7410(2) 0.0767(2) 0.1465(4) 0.0372(11) Uani 1 1 d . . . . .
H3A H 0.7669 0.0377 0.1216 0.056 Uiso 1 1 calc R U . . .
H3B H 0.7090 0.0601 0.1988 0.056 Uiso 1 1 calc R U . . .
H3C H 0.7677 0.1111 0.1835 0.056 Uiso 1 1 calc R U . . .
C4 C 0.66741(19) 0.17239(19) 0.0827(4) 0.0269(10) Uani 1 1 d . . . . .
C5 C 0.6723(2) 0.2143(2) 0.1773(4) 0.0317(11) Uani 1 1 d . . . . .
H5 H 0.7027 0.2076 0.2342 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6258(2) 0.2689(2) 0.1789(4) 0.0427(13) Uani 1 1 d . . . . .
H6 H 0.6223 0.3020 0.2371 0.051 Uiso 1 1 calc R U . . .
C7 C 0.5873(2) 0.2678(2) 0.0873(4) 0.0478(13) Uani 1 1 d . . . . .
H7 H 0.5542 0.2998 0.0747 0.057 Uiso 1 1 calc R U . . .
C8 C 0.57443(18) -0.0184(2) -0.1994(3) 0.0244(9) Uani 1 1 d . . . . .
C9 C 0.63419(19) -0.0643(2) -0.1964(3) 0.0340(11) Uani 1 1 d . . . . .
H9A H 0.6665 -0.0418 -0.1507 0.051 Uiso 1 1 calc R U . . .
H9B H 0.6501 -0.0706 -0.2724 0.051 Uiso 1 1 calc R U . . .
H9C H 0.6238 -0.1095 -0.1642 0.051 Uiso 1 1 calc R U . . .
C10 C 0.5913(2) 0.0552(2) -0.2486(3) 0.0344(10) Uani 1 1 d . . . . .
H10A H 0.6246 0.0763 -0.2036 0.052 Uiso 1 1 calc R U . . .
H10B H 0.5538 0.0847 -0.2471 0.052 Uiso 1 1 calc R U . . .
H10C H 0.6058 0.0500 -0.3256 0.052 Uiso 1 1 calc R U . . .
C11 C 0.52236(19) -0.05168(19) -0.2694(3) 0.0241(9) Uani 1 1 d . . . . .
C12 C 0.4835(2) -0.0217(2) -0.3504(3) 0.0320(10) Uani 1 1 d . . . . .
H12 H 0.4880 0.0246 -0.3757 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4362(2) -0.0680(3) -0.3910(4) 0.0485(14) Uani 1 1 d . . . . .
H13 H 0.4062 -0.0557 -0.4461 0.058 Uiso 1 1 calc R U . . .
C14 C 0.4389(2) -0.1318(3) -0.3418(4) 0.0498(14) Uani 1 1 d . . . . .
H14 H 0.4110 -0.1688 -0.3585 0.060 Uiso 1 1 calc R U . . .
C15 C 0.6753(2) -0.1996(2) 0.1021(4) 0.0476(14) Uani 1 1 d . . . . .
H15A H 0.6758 -0.2069 0.0213 0.071 Uiso 1 1 calc R U . . .
H15B H 0.6646 -0.2431 0.1397 0.071 Uiso 1 1 calc R U . . .
H15C H 0.7168 -0.1839 0.1268 0.071 Uiso 1 1 calc R U . . .
C16 C 0.5598(2) -0.1668(2) 0.0901(4) 0.0438(13) Uani 1 1 d . . . . .
H16A H 0.5613 -0.1743 0.0093 0.066 Uiso 1 1 calc R U . . .
H16B H 0.5288 -0.1309 0.1073 0.066 Uiso 1 1 calc R U . . .
H16C H 0.5480 -0.2101 0.1272 0.066 Uiso 1 1 calc R U . . .
C17 C 0.6252(2) -0.1435(2) 0.1316(4) 0.0320(11) Uani 1 1 d . . . . .
C18 C 0.6261(2) -0.1309(2) 0.2580(4) 0.0350(11) Uani 1 1 d D . . . .
S3 S 0.68353(12) -0.08075(12) 0.31914(18) 0.0580(7) Uani 0.776(5) 1 d D . P A 1
C19 C 0.5871(6) -0.1590(7) 0.3396(10) 0.0564(15) Uani 0.776(5) 1 d D . P A 1
H19 H 0.5532 -0.1892 0.3226 0.068 Uiso 0.776(5) 1 calc R U P A 1
C20 C 0.6022(4) -0.1385(4) 0.4520(6) 0.0564(15) Uani 0.776(5) 1 d D . P A 1
H20 H 0.5795 -0.1528 0.5162 0.068 Uiso 0.776(5) 1 calc R U P A 1
C21 C 0.6539(4) -0.0956(4) 0.4544(5) 0.0564(15) Uani 0.776(5) 1 d D . P A 1
H21 H 0.6713 -0.0764 0.5204 0.068 Uiso 0.776(5) 1 calc R U P A 1
C19' C 0.6768(11) -0.0949(13) 0.305(2) 0.0564(15) Uani 0.224(5) 1 d D . P A 2
H19' H 0.7080 -0.0720 0.2624 0.068 Uiso 0.224(5) 1 calc R U P A 2
S3' S 0.5816(4) -0.1666(5) 0.3598(9) 0.046(3) Uani 0.224(5) 1 d D . P A 2
C21' C 0.6256(12) -0.1292(15) 0.4706(18) 0.0564(15) Uani 0.224(5) 1 d D . P A 2
H21' H 0.6156 -0.1318 0.5476 0.068 Uiso 0.224(5) 1 calc R U P A 2
C20' C 0.6771(12) -0.0958(13) 0.4249(18) 0.0564(15) Uani 0.224(5) 1 d D . P A 2
H20' H 0.7095 -0.0755 0.4685 0.068 Uiso 0.224(5) 1 calc R U P A 2
O1 O 0.66956(12) 0.06078(13) -0.0134(2) 0.0279(7) Uani 1 1 d . . . . .
O2 O 0.54654(12) -0.00906(12) -0.08720(19) 0.0212(6) Uani 1 1 d . . . . .
O3 O 0.64615(12) -0.08094(13) 0.0733(2) 0.0303(7) Uani 1 1 d . . . . .
S1 S 0.60614(6) 0.20084(6) -0.00261(10) 0.0407(3) Uani 1 1 d . . . . .
S2 S 0.49972(6) -0.13740(6) -0.24454(10) 0.0376(3) Uani 1 1 d . . . . .
Bi1 Bi 0.59154(2) 0.01189(2) 0.06885(2) 0.02167(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.412(4) . ?
C1 C4 1.519(5) . ?
C1 C3 1.520(5) . ?
C1 C2 1.522(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.369(5) . ?
C4 S1 1.710(4) . ?
C5 C6 1.417(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.343(6) . ?
C6 H6 0.9300 . ?
C7 S1 1.696(5) . ?
C7 H7 0.9300 . ?
C8 O2 1.452(4) . ?
C8 C11 1.500(5) . ?
C8 C9 1.518(5) . ?
C8 C10 1.547(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.372(5) . ?
C11 S2 1.714(4) . ?
C12 C13 1.401(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.341(6) . ?
C13 H13 0.9300 . ?
C14 S2 1.709(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.526(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.512(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O3 1.436(5) . ?
C17 C18 1.505(6) . ?
C18 C19 1.365(11) . ?
C18 C19' 1.375(18) . ?
C18 S3' 1.658(9) . ?
C18 S3 1.687(5) . ?
S3 C21 1.729(6) . ?
C19 C20 1.412(13) . ?
C19 H19 0.9300 . ?
C20 C21 1.348(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C19' C20' 1.403(19) . ?
C19' H19' 0.9300 . ?
S3' C21' 1.744(16) . ?
C21' C20' 1.356(18) . ?
C21' H21' 0.9300 . ?
C20' H20' 0.9300 . ?
O1 Bi1 2.105(2) . ?
O2 Bi1 2.097(2) . ?
O3 Bi1 2.093(2) . ?

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
O1 C1 C4 109.5(3) . . ?
O1 C1 C3 110.9(3) . . ?
C4 C1 C3 109.9(3) . . ?
O1 C1 C2 106.1(3) . . ?
C4 C1 C2 109.9(3) . . ?
C3 C1 C2 110.5(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C1 130.3(4) . . ?
C5 C4 S1 110.4(3) . . ?
C1 C4 S1 119.2(3) . . ?
C4 C5 C6 112.5(4) . . ?
C4 C5 H5 123.7 . . ?
C6 C5 H5 123.7 . . ?
C7 C6 C5 112.7(4) . . ?
C7 C6 H6 123.7 . . ?
C5 C6 H6 123.7 . . ?
C6 C7 S1 111.9(4) . . ?
C6 C7 H7 124.0 . . ?
S1 C7 H7 124.0 . . ?
O2 C8 C11 105.1(3) . . ?
O2 C8 C9 112.1(3) . . ?
C11 C8 C9 111.4(3) . . ?
O2 C8 C10 108.7(3) . . ?
C11 C8 C10 109.6(3) . . ?
C9 C8 C10 109.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 129.3(3) . . ?
C12 C11 S2 110.3(3) . . ?
C8 C11 S2 120.2(3) . . ?
C11 C12 C13 113.1(4) . . ?
C11 C12 H12 123.5 . . ?
C13 C12 H12 123.5 . . ?
C14 C13 C12 112.8(4) . . ?
C14 C13 H13 123.6 . . ?
C12 C13 H13 123.6 . . ?
C13 C14 S2 112.0(4) . . ?
C13 C14 H14 124.0 . . ?
S2 C14 H14 124.0 . . ?
C17 C15 H15A 109.5 . . ?
C17 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C17 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C18 109.6(3) . . ?
O3 C17 C16 111.1(3) . . ?
C18 C17 C16 112.1(4) . . ?
O3 C17 C15 104.9(3) . . ?
C18 C17 C15 109.0(4) . . ?
C16 C17 C15 109.8(4) . . ?
C19 C18 C17 128.6(7) . . ?
C19' C18 C17 119.3(12) . . ?
C19' C18 S3' 109.9(12) . . ?
C17 C18 S3' 129.8(5) . . ?
C19 C18 S3 110.0(7) . . ?
C17 C18 S3 121.2(3) . . ?
C18 S3 C21 92.7(3) . . ?
C18 C19 C20 114.6(10) . . ?
C18 C19 H19 122.7 . . ?
C20 C19 H19 122.7 . . ?
C21 C20 C19 111.3(8) . . ?
C21 C20 H20 124.3 . . ?
C19 C20 H20 124.3 . . ?
C20 C21 S3 111.3(6) . . ?
C20 C21 H21 124.3 . . ?
S3 C21 H21 124.3 . . ?
C18 C19' C20' 114(2) . . ?
C18 C19' H19' 123.1 . . ?
C20' C19' H19' 123.1 . . ?
C18 S3' C21' 94.5(10) . . ?
C20' C21' S3' 108.1(17) . . ?
C20' C21' H21' 126.0 . . ?
S3' C21' H21' 126.0 . . ?
C21' C20' C19' 113(2) . . ?
C21' C20' H20' 123.3 . . ?
C19' C20' H20' 123.3 . . ?
C1 O1 Bi1 120.9(2) . . ?
C8 O2 Bi1 129.7(2) . . ?
C17 O3 Bi1 122.6(2) . . ?
C7 S1 C4 92.5(2) . . ?
C14 S2 C11 91.8(2) . . ?
O3 Bi1 O2 96.10(10) . . ?
O3 Bi1 O1 87.73(10) . . ?
O2 Bi1 O1 91.54(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
O1 C1 C4 C5 146.7(4) . . . . ?
C3 C1 C4 C5 24.6(5) . . . . ?
C2 C1 C4 C5 -97.2(5) . . . . ?
O1 C1 C4 S1 -36.3(4) . . . . ?
C3 C1 C4 S1 -158.4(3) . . . . ?
C2 C1 C4 S1 79.8(4) . . . . ?
C1 C4 C5 C6 177.3(4) . . . . ?
S1 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C5 C6 C7 S1 0.0(5) . . . . ?
O2 C8 C11 C12 103.8(4) . . . . ?
C9 C8 C11 C12 -134.5(4) . . . . ?
C10 C8 C11 C12 -12.9(6) . . . . ?
O2 C8 C11 S2 -70.4(4) . . . . ?
C9 C8 C11 S2 51.3(4) . . . . ?
C10 C8 C11 S2 173.0(3) . . . . ?
C8 C11 C12 C13 -174.6(4) . . . . ?
S2 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 S2 -0.3(6) . . . . ?
O3 C17 C18 C19 148.5(8) . . . . ?
C16 C17 C18 C19 24.7(9) . . . . ?
C15 C17 C18 C19 -97.2(8) . . . . ?
O3 C17 C18 C19' -41.8(13) . . . . ?
C16 C17 C18 C19' -165.7(13) . . . . ?
C15 C17 C18 C19' 72.5(13) . . . . ?
O3 C17 C18 S3' 151.5(5) . . . . ?
C16 C17 C18 S3' 27.6(7) . . . . ?
C15 C17 C18 S3' -94.3(6) . . . . ?
O3 C17 C18 S3 -36.2(5) . . . . ?
C16 C17 C18 S3 -160.0(3) . . . . ?
C15 C17 C18 S3 78.1(4) . . . . ?
C19 C18 S3 C21 -1.5(7) . . . . ?
C19' C18 S3 C21 -108(13) . . . . ?
C17 C18 S3 C21 -177.6(4) . . . . ?
S3' C18 S3 C21 -3.8(5) . . . . ?
C19' C18 C19 C20 7.1(17) . . . . ?
C17 C18 C19 C20 177.4(6) . . . . ?
S3' C18 C19 C20 59(21) . . . . ?
S3 C18 C19 C20 1.7(11) . . . . ?
C18 C19 C20 C21 -1.1(12) . . . . ?
C19 C20 C21 S3 -0.1(9) . . . . ?
C18 S3 C21 C20 0.9(6) . . . . ?
C19 C18 C19' C20' 0.6(18) . . . . ?
C17 C18 C19' C20' -170.8(11) . . . . ?
S3' C18 C19' C20' -1.6(16) . . . . ?
S3 C18 C19' C20' 76(13) . . . . ?
C19 C18 S3' C21' -125(21) . . . . ?
C19' C18 S3' C21' 4.2(16) . . . . ?
C17 C18 S3' C21' 171.9(11) . . . . ?
S3 C18 S3' C21' -1.2(11) . . . . ?
C18 S3' C21' C20' -5.8(19) . . . . ?
S3' C21' C20' C19' 6(2) . . . . ?
C18 C19' C20' C21' -3.0(19) . . . . ?
C4 C1 O1 Bi1 -60.1(3) . . . . ?
C3 C1 O1 Bi1 61.3(4) . . . . ?
C2 C1 O1 Bi1 -178.7(2) . . . . ?
C11 C8 O2 Bi1 164.5(2) . . . . ?
C9 C8 O2 Bi1 43.3(4) . . . . ?
C10 C8 O2 Bi1 -78.2(3) . . . . ?
C18 C17 O3 Bi1 -69.1(4) . . . . ?
C16 C17 O3 Bi1 55.4(4) . . . . ?
C15 C17 O3 Bi1 174.0(3) . . . . ?
C6 C7 S1 C4 0.0(4) . . . . ?
C5 C4 S1 C7 -0.1(3) . . . . ?
C1 C4 S1 C7 -177.6(3) . . . . ?
C13 C14 S2 C11 0.2(4) . . . . ?
C12 C11 S2 C14 -0.1(3) . . . . ?
C8 C11 S2 C14 175.0(3) . . . . ?

_refine_diff_density_max         0.866
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-4


# start Validation Reply Form
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact  O2     ..  O2      ..       2.84 Ang.  
RESPONSE: 

This short intermolecular distance is originated by an intermolecular Bi-O2
interaction. Most likely due to this interaction the O2...O2a distance is
shorter than expected or might  contribute to the stabilization of the dimer, 
cf. accompanying manuscript.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1541507'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Bi N3'
_chemical_formula_weight         449.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1009(10)
_cell_length_b                   8.0234(11)
_cell_length_c                   13.7128(15)
_cell_angle_alpha                77.669(11)
_cell_angle_beta                 75.569(11)
_cell_angle_gamma                83.657(11)
_cell_volume                     737.80(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    110
_cell_measurement_reflns_used    1607
_cell_measurement_theta_min      5.6510
_cell_measurement_theta_max      66.3130
_cell_oxdiff_twin_number         2
loop_
_cell_oxdiff_twin_id
_cell_oxdiff_twin_matrix_11
_cell_oxdiff_twin_matrix_12
_cell_oxdiff_twin_matrix_13
_cell_oxdiff_twin_matrix_21
_cell_oxdiff_twin_matrix_22
_cell_oxdiff_twin_matrix_23
_cell_oxdiff_twin_matrix_31
_cell_oxdiff_twin_matrix_32
_cell_oxdiff_twin_matrix_33
1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000
2 0.9868 0.0566 0.0127 -0.0879 0.9987 0.0186 -0.0700 -0.0260 1.0107




_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.022
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    23.361
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.71571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5559
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.392
_diffrn_reflns_theta_max         63.996
_diffrn_reflns_theta_full        64.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_orient_matrix_UB_11      0.0443271000
_diffrn_orient_matrix_UB_12      0.1139561000
_diffrn_orient_matrix_UB_13      -0.1077178000
_diffrn_orient_matrix_UB_21      0.0743009000
_diffrn_orient_matrix_UB_22      -0.1593558000
_diffrn_orient_matrix_UB_23      -0.0474787000
_diffrn_orient_matrix_UB_31      -0.2069910000
_diffrn_orient_matrix_UB_32      -0.0198125000
_diffrn_orient_matrix_UB_33      -0.0105463000
_diffrn_oxdiff_twin_integration_method simultaneous
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.5769 1977 1549
2 0.4231 2033 1549

_reflns_number_total             4179
_reflns_number_gt                3481
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4179
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0959
_refine_ls_wR_factor_ref         0.2733
_refine_ls_wR_factor_gt          0.2606
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.834(4) 0.076(3) 0.7236(19) 0.041(6) Uani 1 1 d . . . . .
C2 C 0.994(3) 0.113(3) 0.7538(18) 0.031(4) Uani 1 1 d . . . . .
H2 H 1.0099 0.0902 0.8209 0.037 Uiso 1 1 calc R U . . .
C3 C 1.133(4) 0.192(3) 0.665(2) 0.040(5) Uani 1 1 d . . . . .
H3 H 1.2526 0.2304 0.6631 0.048 Uiso 1 1 calc R U . . .
C4 C 1.052(4) 0.197(3) 0.583(2) 0.046(6) Uani 1 1 d . . . . .
H4 H 1.1092 0.2406 0.5151 0.056 Uiso 1 1 calc R U . . .
C5 C 0.731(4) 0.124(4) 0.554(2) 0.047(6) Uani 1 1 d . . . . .
H5A H 0.7885 0.1736 0.4839 0.071 Uiso 1 1 calc R U . . .
H5B H 0.6117 0.1874 0.5773 0.071 Uiso 1 1 calc R U . . .
H5C H 0.7040 0.0074 0.5576 0.071 Uiso 1 1 calc R U . . .
C6 C 0.663(3) -0.188(3) 0.9444(16) 0.031(4) Uani 1 1 d . . . . .
C7 C 0.846(3) -0.217(3) 0.967(2) 0.046(6) Uani 1 1 d . . . . .
H7 H 0.9612 -0.1708 0.9266 0.055 Uiso 1 1 calc R U . . .
C8 C 0.822(4) -0.327(3) 1.062(2) 0.042(6) Uani 1 1 d . . . . .
H8 H 0.9213 -0.3671 1.0957 0.050 Uiso 1 1 calc R U . . .
C9 C 0.638(3) -0.366(3) 1.0982(17) 0.033(5) Uani 1 1 d . . . . .
H9 H 0.5865 -0.4393 1.1594 0.040 Uiso 1 1 calc R U . . .
C10 C 0.327(4) -0.289(4) 1.032(2) 0.050(7) Uani 1 1 d . . . . .
H10A H 0.2905 -0.2183 0.9731 0.075 Uiso 1 1 calc R U . . .
H10B H 0.2513 -0.2530 1.0931 0.075 Uiso 1 1 calc R U . . .
H10C H 0.3042 -0.4060 1.0347 0.075 Uiso 1 1 calc R U . . .
C11 C 0.564(3) -0.243(3) 0.7257(16) 0.035(5) Uani 1 1 d . . . . .
C12 C 0.421(4) -0.273(3) 0.690(2) 0.046(6) Uani 1 1 d . . . . .
H12 H 0.2995 -0.2136 0.6980 0.056 Uiso 1 1 calc R U . . .
C13 C 0.483(4) -0.413(3) 0.6369(19) 0.040(5) Uani 1 1 d . . . . .
H13 H 0.4132 -0.4575 0.6004 0.048 Uiso 1 1 calc R U . . .
C14 C 0.666(3) -0.466(3) 0.6508(18) 0.037(5) Uani 1 1 d . . . . .
H14 H 0.7408 -0.5580 0.6277 0.044 Uiso 1 1 calc R U . . .
C15 C 0.909(3) -0.371(3) 0.726(2) 0.040(5) Uani 1 1 d . . . . .
H15A H 0.9156 -0.2873 0.7655 0.060 Uiso 1 1 calc R U . . .
H15B H 1.0051 -0.3499 0.6619 0.060 Uiso 1 1 calc R U . . .
H15C H 0.9342 -0.4830 0.7631 0.060 Uiso 1 1 calc R U . . .
N1 N 0.868(3) 0.127(3) 0.6195(15) 0.040(4) Uani 1 1 d . . . . .
N2 N 0.534(2) -0.275(3) 1.0247(15) 0.034(4) Uani 1 1 d . . . . .
N3 N 0.722(3) -0.358(2) 0.7057(15) 0.036(4) Uani 1 1 d . . . . .
Bi1 Bi 0.54828(11) -0.02839(10) 0.81326(6) 0.0350(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.37(3) . ?
C1 C2 1.39(4) . ?
C1 Bi1 2.24(2) . ?
C2 C3 1.44(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.37(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.41(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.49(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N2 1.36(3) . ?
C6 C7 1.39(3) . ?
C6 Bi1 2.25(2) . ?
C7 C8 1.39(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.32(4) . ?
C8 H8 0.9300 . ?
C9 N2 1.43(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.46(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.30(4) . ?
C11 N3 1.38(3) . ?
C11 Bi1 2.28(2) . ?
C12 C13 1.44(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.37(3) . ?
C13 H13 0.9300 . ?
C14 N3 1.40(3) . ?
C14 H14 0.9300 . ?
C15 N3 1.41(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 107(2) . . ?
N1 C1 Bi1 120.6(19) . . ?
C2 C1 Bi1 132.0(19) . . ?
C1 C2 C3 109(2) . . ?
C1 C2 H2 125.5 . . ?
C3 C2 H2 125.5 . . ?
C4 C3 C2 106(2) . . ?
C4 C3 H3 127.2 . . ?
C2 C3 H3 127.2 . . ?
C3 C4 N1 109(2) . . ?
C3 C4 H4 125.5 . . ?
N1 C4 H4 125.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 108(2) . . ?
N2 C6 Bi1 117.9(15) . . ?
C7 C6 Bi1 134.0(18) . . ?
C6 C7 C8 106(2) . . ?
C6 C7 H7 126.8 . . ?
C8 C7 H7 126.8 . . ?
C9 C8 C7 111(2) . . ?
C9 C8 H8 124.6 . . ?
C7 C8 H8 124.6 . . ?
C8 C9 N2 106(2) . . ?
C8 C9 H9 126.8 . . ?
N2 C9 H9 126.8 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N3 112(2) . . ?
C12 C11 Bi1 123(2) . . ?
N3 C11 Bi1 125.3(15) . . ?
C11 C12 C13 108(2) . . ?
C11 C12 H12 126.1 . . ?
C13 C12 H12 126.1 . . ?
C14 C13 C12 106(2) . . ?
C14 C13 H13 127.2 . . ?
C12 C13 H13 127.2 . . ?
C13 C14 N3 109(2) . . ?
C13 C14 H14 125.5 . . ?
N3 C14 H14 125.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 C4 109(2) . . ?
C1 N1 C5 126(2) . . ?
C4 N1 C5 124(2) . . ?
C6 N2 C9 108.4(18) . . ?
C6 N2 C10 127(2) . . ?
C9 N2 C10 124(2) . . ?
C11 N3 C14 105.2(18) . . ?
C11 N3 C15 132(2) . . ?
C14 N3 C15 123(2) . . ?
C1 Bi1 C6 96.0(10) . . ?
C1 Bi1 C11 95.7(8) . . ?
C6 Bi1 C11 96.1(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
N1 C1 C2 C3 0(3) . . . . ?
Bi1 C1 C2 C3 -175.1(16) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
C2 C3 C4 N1 1(3) . . . . ?
N2 C6 C7 C8 2(3) . . . . ?
Bi1 C6 C7 C8 178.3(17) . . . . ?
C6 C7 C8 C9 0(3) . . . . ?
C7 C8 C9 N2 -1(3) . . . . ?
N3 C11 C12 C13 -3(3) . . . . ?
Bi1 C11 C12 C13 178.2(15) . . . . ?
C11 C12 C13 C14 4(3) . . . . ?
C12 C13 C14 N3 -3(3) . . . . ?
C2 C1 N1 C4 0(3) . . . . ?
Bi1 C1 N1 C4 176.2(15) . . . . ?
C2 C1 N1 C5 -176(2) . . . . ?
Bi1 C1 N1 C5 0(3) . . . . ?
C3 C4 N1 C1 -1(3) . . . . ?
C3 C4 N1 C5 175(2) . . . . ?
C7 C6 N2 C9 -3(3) . . . . ?
Bi1 C6 N2 C9 -179.8(14) . . . . ?
C7 C6 N2 C10 -177(2) . . . . ?
Bi1 C6 N2 C10 6(3) . . . . ?
C8 C9 N2 C6 2(2) . . . . ?
C8 C9 N2 C10 177(2) . . . . ?
C12 C11 N3 C14 1(3) . . . . ?
Bi1 C11 N3 C14 179.8(15) . . . . ?
C12 C11 N3 C15 177(2) . . . . ?
Bi1 C11 N3 C15 -4(3) . . . . ?
C13 C14 N3 C11 1(2) . . . . ?
C13 C14 N3 C15 -175(2) . . . . ?

_refine_diff_density_max         5.208
_refine_diff_density_min         -4.943
_refine_diff_density_rms         0.450

_shelxl_version_number           2013-4


# start Validation Reply Form
_vrf_PLAT342_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0378 Ang.  
RESPONSE: All crystals made available were twinned. The finally chosen one
comprise two nearly equally populated domains. The number of overlapping
reflections is comparatively high, which seems to be responsible for
the lower accuracy.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1541505'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Bi S3'
_chemical_formula_sum            'C12 H9 Bi S3'
_chemical_formula_weight         458.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9848(8)
_cell_length_b                   9.3411(7)
_cell_length_c                   9.6115(11)
_cell_angle_alpha                64.493(9)
_cell_angle_beta                 71.427(9)
_cell_angle_gamma                66.556(8)
_cell_volume                     657.31(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6511
_cell_measurement_theta_min      2.8540
_cell_measurement_theta_max      25.9984

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.316
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    13.856
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Gemini S'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6252
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.862
_diffrn_reflns_theta_max         26.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2572
_reflns_number_gt                2356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0237P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2572
_refine_ls_number_parameters     183
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0473
_refine_ls_wR_factor_gt          0.0461
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.64541(2) 0.64547(2) 0.52928(2) 0.02021(7) Uani 1 1 d . . . . .
S2 S 0.7506(3) 0.9064(4) 0.6260(4) 0.0302(7) Uani 0.699(6) 1 d D U P A 1
C6 C 0.4746(19) 0.857(2) 0.768(2) 0.027(3) Uani 0.699(6) 1 d D U P A 1
H6 H 0.3833 0.8193 0.8038 0.032 Uiso 0.699(6) 1 calc R U P A 1
S2' S 0.4344(12) 0.8563(16) 0.7871(14) 0.0282(19) Uani 0.301(6) 1 d D U P A 2
C6' C 0.699(3) 0.914(4) 0.637(3) 0.028(5) Uani 0.301(6) 1 d D U P A 2
H6' H 0.7905 0.9242 0.5584 0.034 Uiso 0.301(6) 1 calc R U P A 2
C1 C 0.8034(6) 0.4327(5) 0.6972(5) 0.0213(9) Uani 1 1 d . U . . .
C5 C 0.6089(6) 0.8113(5) 0.6579(5) 0.0221(9) Uani 1 1 d D U . . .
S1 S 0.95663(18) 0.27114(17) 0.64899(16) 0.0369(3) Uani 1 1 d . U . . .
C2 C 0.7945(5) 0.4087(5) 0.8573(4) 0.0154(8) Uani 1 1 d . U . . .
H2 H 0.7212 0.4816 0.9085 0.018 Uiso 1 1 calc R U . . .
C9 C 0.4189(6) 0.5707(5) 0.6798(5) 0.0223(9) Uani 1 1 d D U . . .
C3 C 0.9128(7) 0.2589(6) 0.9260(6) 0.0355(11) Uani 1 1 d . U . . .
H3 H 0.9243 0.2219 1.0298 0.043 Uiso 1 1 calc R U . . .
S3 S 0.2275(4) 0.6839(4) 0.6374(5) 0.0268(8) Uani 0.603(5) 1 d D U P B 1
C10 C 0.414(3) 0.424(2) 0.810(2) 0.028(4) Uani 0.603(5) 1 d D U P B 1
H10 H 0.5045 0.3431 0.8534 0.033 Uiso 0.603(5) 1 calc R U P B 1
S3' S 0.4361(9) 0.3910(9) 0.8313(9) 0.0242(13) Uani 0.397(5) 1 d D U P B 2
C10' C 0.251(3) 0.648(3) 0.664(3) 0.035(5) Uani 0.397(5) 1 d D U P B 2
H10' H 0.2134 0.7510 0.5881 0.043 Uiso 0.397(5) 1 calc R U P B 2
C7 C 0.4932(7) 0.9740(6) 0.8231(6) 0.0319(11) Uani 1 1 d D U . . .
H7 H 0.4171 1.0187 0.8970 0.038 Uiso 1 1 calc R U . A 1
C11 C 0.2412(7) 0.4157(7) 0.8683(6) 0.0331(11) Uani 1 1 d D U . . .
H11 H 0.2082 0.3300 0.9529 0.040 Uiso 1 1 calc R U . B 1
C8 C 0.6367(7) 1.0050(6) 0.7494(6) 0.0333(12) Uani 1 1 d D U . . .
H8 H 0.6701 1.0774 0.7666 0.040 Uiso 1 1 calc R U . A 1
C4 C 1.0067(7) 0.1749(6) 0.8304(6) 0.0381(12) Uani 1 1 d . U . . .
H4 H 1.0902 0.0749 0.8598 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1422(7) 0.5501(7) 0.7805(6) 0.0381(12) Uani 1 1 d D U . . .
H12 H 0.0294 0.5673 0.7997 0.046 Uiso 1 1 calc R U . B 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.241(5) . ?
Bi1 C5 2.241(4) . ?
Bi1 C9 2.260(4) . ?
S2 C8 1.649(5) . ?
S2 C5 1.709(4) . ?
C6 C5 1.391(14) . ?
C6 C7 1.478(16) . ?
C6 H6 0.9300 . ?
S2' C7 1.586(11) . ?
S2' C5 1.692(9) . ?
C6' C5 1.394(19) . ?
C6' C8 1.50(2) . ?
C6' H6' 0.9300 . ?
C1 C2 1.437(6) . ?
C1 S1 1.712(5) . ?
S1 C4 1.697(6) . ?
C2 C3 1.411(7) . ?
C2 H2 0.9300 . ?
C9 C10 1.411(17) . ?
C9 C10' 1.41(2) . ?
C9 S3' 1.672(7) . ?
C9 S3 1.694(6) . ?
C3 C4 1.331(8) . ?
C3 H3 0.9300 . ?
S3 C12 1.628(6) . ?
C10 C11 1.49(2) . ?
C10 H10 0.9300 . ?
S3' C11 1.612(10) . ?
C10' C12 1.48(2) . ?
C10' H10' 0.9300 . ?
C7 C8 1.337(7) . ?
C7 H7 0.9300 . ?
C11 C12 1.325(8) . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 C5 90.08(15) . . ?
C1 Bi1 C9 90.75(16) . . ?
C5 Bi1 C9 91.68(14) . . ?
C8 S2 C5 93.5(2) . . ?
C5 C6 C7 112.4(10) . . ?
C5 C6 H6 123.8 . . ?
C7 C6 H6 123.8 . . ?
C7 S2' C5 93.3(5) . . ?
C5 C6' C8 115.4(15) . . ?
C5 C6' H6' 122.3 . . ?
C8 C6' H6' 122.3 . . ?
C2 C1 S1 109.7(3) . . ?
C2 C1 Bi1 126.9(3) . . ?
S1 C1 Bi1 123.4(2) . . ?
C6' C5 S2' 106.7(8) . . ?
C6 C5 S2 109.4(7) . . ?
C6 C5 Bi1 128.2(7) . . ?
C6' C5 Bi1 131.0(9) . . ?
S2' C5 Bi1 121.6(4) . . ?
S2 C5 Bi1 122.4(2) . . ?
C4 S1 C1 93.0(3) . . ?
C3 C2 C1 110.4(4) . . ?
C3 C2 H2 124.8 . . ?
C1 C2 H2 124.8 . . ?
C10' C9 S3' 108.8(9) . . ?
C10 C9 S3 110.3(8) . . ?
C10 C9 Bi1 127.2(9) . . ?
C10' C9 Bi1 130.5(9) . . ?
S3' C9 Bi1 120.6(4) . . ?
S3 C9 Bi1 122.3(2) . . ?
C4 C3 C2 114.7(5) . . ?
C4 C3 H3 122.7 . . ?
C2 C3 H3 122.7 . . ?
C12 S3 C9 93.3(3) . . ?
C9 C10 C11 110.2(12) . . ?
C9 C10 H10 124.9 . . ?
C11 C10 H10 124.9 . . ?
C11 S3' C9 92.9(4) . . ?
C9 C10' C12 113.4(15) . . ?
C9 C10' H10' 123.3 . . ?
C12 C10' H10' 123.3 . . ?
C8 C7 C6 109.1(6) . . ?
C8 C7 S2' 121.6(5) . . ?
C8 C7 H7 125.4 . . ?
C6 C7 H7 125.4 . . ?
C12 C11 C10 109.3(8) . . ?
C12 C11 S3' 120.0(5) . . ?
C12 C11 H11 125.4 . . ?
C10 C11 H11 125.4 . . ?
C7 C8 C6' 102.1(8) . . ?
C7 C8 S2 115.6(3) . . ?
C7 C8 H8 122.2 . . ?
S2 C8 H8 122.2 . . ?
C3 C4 S1 112.3(4) . . ?
C3 C4 H4 123.9 . . ?
S1 C4 H4 123.9 . . ?
C11 C12 C10' 104.9(9) . . ?
C11 C12 S3 116.9(5) . . ?
C11 C12 H12 121.6 . . ?
S3 C12 H12 121.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C6 C5 S2 0.5(16) . . . . ?
C7 C6 C5 Bi1 -177.9(6) . . . . ?
C8 C6' C5 S2' 11(3) . . . . ?
C8 C6' C5 Bi1 -179.1(9) . . . . ?
C7 S2' C5 C6' -7.3(17) . . . . ?
C7 S2' C5 Bi1 -178.6(4) . . . . ?
C8 S2 C5 C6 -1.0(10) . . . . ?
C8 S2 C5 Bi1 177.5(3) . . . . ?
C2 C1 S1 C4 0.4(3) . . . . ?
Bi1 C1 S1 C4 -179.7(2) . . . . ?
S1 C1 C2 C3 -0.8(4) . . . . ?
Bi1 C1 C2 C3 179.3(3) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C10 C9 S3 C12 0.3(12) . . . . ?
Bi1 C9 S3 C12 175.7(3) . . . . ?
S3 C9 C10 C11 -0.1(19) . . . . ?
Bi1 C9 C10 C11 -175.2(7) . . . . ?
C10' C9 S3' C11 0.6(15) . . . . ?
Bi1 C9 S3' C11 -175.7(3) . . . . ?
S3' C9 C10' C12 -1(2) . . . . ?
Bi1 C9 C10' C12 174.6(8) . . . . ?
C5 C6 C7 C8 0.4(17) . . . . ?
C5 S2' C7 C8 2.3(10) . . . . ?
C9 C10 C11 C12 -0.1(19) . . . . ?
C9 S3' C11 C12 0.2(7) . . . . ?
S2' C7 C8 C6' 3.1(15) . . . . ?
C6 C7 C8 S2 -1.2(10) . . . . ?
C5 C6' C8 C7 -9(2) . . . . ?
C5 S2 C8 C7 1.3(5) . . . . ?
C2 C3 C4 S1 -0.7(5) . . . . ?
C1 S1 C4 C3 0.1(4) . . . . ?
S3' C11 C12 C10' -0.8(14) . . . . ?
C10 C11 C12 S3 0.3(12) . . . . ?
C9 C10' C12 C11 1(2) . . . . ?
C9 S3 C12 C11 -0.4(5) . . . . ?

_refine_diff_density_max         1.236
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.135

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 1541502'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Bi Se3'
_chemical_formula_sum            'C12 H9 Bi Se3'
_chemical_formula_weight         599.05

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2842(4)
_cell_length_b                   8.3495(7)
_cell_length_c                   13.7048(11)
_cell_angle_alpha                77.414(7)
_cell_angle_beta                 79.252(6)
_cell_angle_gamma                81.297(6)
_cell_volume                     684.89(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120
_cell_measurement_reflns_used    1747
_cell_measurement_theta_min      3.5790
_cell_measurement_theta_max      27.4160

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.905
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    20.813
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.44330
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4287
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.085
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2384
_reflns_number_gt                2062
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2384
_refine_ls_number_parameters     164
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3552(14) 0.1849(11) 0.0570(7) 0.022(2) Uani 1 1 d D U . . .
Se1 Se 0.0627(2) 0.1990(2) 0.05044(12) 0.0290(5) Uani 0.765(4) 1 d D U P A 1
C2 C 0.464(4) 0.294(3) -0.0237(17) 0.028(5) Uani 0.765(4) 1 d D U P A 1
H2 H 0.6114 0.3060 -0.0337 0.034 Uiso 0.765(4) 1 calc R U P A 1
C2' C 0.142(6) 0.210(7) 0.033(4) 0.036(14) Uani 0.235(4) 1 d D U P A 2
H2' H 0.0342 0.1456 0.0698 0.044 Uiso 0.235(4) 1 calc R U P A 2
Se1' Se 0.5110(11) 0.3184(9) -0.0468(5) 0.0249(17) Uani 0.235(4) 1 d D U P A 2
C3 C 0.2998(18) 0.3900(12) -0.0929(8) 0.030(2) Uani 1 1 d D U . . .
H3 H 0.3387 0.4667 -0.1515 0.036 Uiso 1 1 calc R U . A 1
C4 C 0.0963(19) 0.3517(13) -0.0598(9) 0.038(3) Uani 1 1 d D U . . .
H4 H -0.0196 0.4026 -0.0931 0.045 Uiso 1 1 calc R U . A 1
C5 C 0.2328(16) -0.0853(11) 0.2651(7) 0.019(2) Uani 1 1 d . U . . .
C6 C 0.0862(14) -0.1727(10) 0.2397(7) 0.0169(19) Uani 1 1 d . U . . .
H6 H 0.0918 -0.1878 0.1740 0.020 Uiso 1 1 calc R U . . .
Se2 Se 0.17291(18) -0.08643(12) 0.40418(8) 0.0282(3) Uani 1 1 d . U . . .
C7 C -0.0727(18) -0.2372(12) 0.3212(8) 0.031(2) Uani 1 1 d . U . . .
H7 H -0.1812 -0.2947 0.3124 0.038 Uiso 1 1 calc R U . . .
C8 C -0.0545(17) -0.2091(11) 0.4116(8) 0.029(2) Uani 1 1 d . U . . .
H8 H -0.1455 -0.2469 0.4714 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5025(16) 0.2147(10) 0.2645(8) 0.022(2) Uani 1 1 d . U . . .
C10 C 0.6602(17) 0.2328(10) 0.3177(8) 0.023(2) Uani 1 1 d . U . . .
H10 H 0.7900 0.1629 0.3201 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6041(18) 0.3719(11) 0.3698(8) 0.029(2) Uani 1 1 d . U . . .
H11 H 0.6954 0.3979 0.4088 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4101(18) 0.4596(11) 0.3570(8) 0.027(2) Uani 1 1 d . U . . .
H12 H 0.3549 0.5522 0.3851 0.033 Uiso 1 1 calc R U . . .
Se3 Se 0.26640(16) 0.37580(11) 0.27777(8) 0.0257(3) Uani 1 1 d . U . . .
Bi1 Bi 0.53293(6) 0.01730(4) 0.17307(3) 0.01960(15) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.408(19) . ?
C1 C2' 1.41(3) . ?
C1 Se1' 1.829(8) . ?
C1 Se1 1.842(9) . ?
C1 Bi1 2.226(10) . ?
Se1 C4 1.754(11) . ?
C2 C3 1.55(3) . ?
C2 H2 0.9300 . ?
C2' C4 1.57(3) . ?
C2' H2' 0.9300 . ?
Se1' C3 1.557(14) . ?
C3 C4 1.337(14) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.392(14) . ?
C5 Se2 1.871(10) . ?
C5 Bi1 2.239(9) . ?
C6 C7 1.421(12) . ?
C6 H6 0.9300 . ?
Se2 C8 1.856(11) . ?
C7 C8 1.338(16) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.377(15) . ?
C9 Se3 1.856(9) . ?
C9 Bi1 2.245(10) . ?
C10 C11 1.459(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.344(14) . ?
C11 H11 0.9300 . ?
C12 Se3 1.837(12) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' C1 Se1' 104.7(16) . . ?
C2 C1 Se1 111.9(12) . . ?
C2 C1 Bi1 121.4(12) . . ?
C2' C1 Bi1 136.6(15) . . ?
Se1' C1 Bi1 118.4(5) . . ?
Se1 C1 Bi1 126.6(4) . . ?
C4 Se1 C1 89.9(5) . . ?
C1 C2 C3 109.5(16) . . ?
C1 C2 H2 125.2 . . ?
C3 C2 H2 125.2 . . ?
C1 C2' C4 116(2) . . ?
C1 C2' H2' 121.8 . . ?
C4 C2' H2' 121.8 . . ?
C3 Se1' C1 90.6(6) . . ?
C4 C3 C2 113.1(11) . . ?
C4 C3 Se1' 129.0(9) . . ?
C4 C3 H3 123.5 . . ?
C2 C3 H3 123.5 . . ?
C3 C4 C2' 98.7(16) . . ?
C3 C4 Se1 115.5(9) . . ?
C3 C4 H4 122.2 . . ?
Se1 C4 H4 122.2 . . ?
C6 C5 Se2 109.6(6) . . ?
C6 C5 Bi1 130.4(7) . . ?
Se2 C5 Bi1 119.4(5) . . ?
C5 C6 C7 115.3(10) . . ?
C5 C6 H6 122.4 . . ?
C7 C6 H6 122.4 . . ?
C8 Se2 C5 87.7(5) . . ?
C8 C7 C6 115.0(11) . . ?
C8 C7 H7 122.5 . . ?
C6 C7 H7 122.5 . . ?
C7 C8 Se2 112.4(8) . . ?
C7 C8 H8 123.8 . . ?
Se2 C8 H8 123.8 . . ?
C10 C9 Se3 111.0(7) . . ?
C10 C9 Bi1 123.9(7) . . ?
Se3 C9 Bi1 125.1(6) . . ?
C9 C10 C11 113.6(9) . . ?
C9 C10 H10 123.2 . . ?
C11 C10 H10 123.2 . . ?
C12 C11 C10 114.7(11) . . ?
C12 C11 H11 122.6 . . ?
C10 C11 H11 122.6 . . ?
C11 C12 Se3 112.3(8) . . ?
C11 C12 H12 123.8 . . ?
Se3 C12 H12 123.8 . . ?
C12 Se3 C9 88.3(5) . . ?
C1 Bi1 C5 94.3(3) . . ?
C1 Bi1 C9 92.1(4) . . ?
C5 Bi1 C9 92.1(3) . . ?

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
C2 C1 Se1 C4 -0.4(14) . . . . ?
C2' C1 Se1 C4 -19(15) . . . . ?
Se1' C1 Se1 C4 -1.9(7) . . . . ?
Bi1 C1 Se1 C4 -179.3(7) . . . . ?
C2' C1 C2 C3 3(4) . . . . ?
Se1' C1 C2 C3 155(25) . . . . ?
Se1 C1 C2 C3 0(2) . . . . ?
Bi1 C1 C2 C3 178.5(10) . . . . ?
C2 C1 C2' C4 -6(5) . . . . ?
Se1' C1 C2' C4 -8(5) . . . . ?
Se1 C1 C2' C4 156(19) . . . . ?
Bi1 C1 C2' C4 179.3(15) . . . . ?
C2 C1 Se1' C3 -23(23) . . . . ?
C2' C1 Se1' C3 5(3) . . . . ?
Se1 C1 Se1' C3 1.8(8) . . . . ?
Bi1 C1 Se1' C3 179.4(6) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C1 C2 C3 Se1' -174(6) . . . . ?
C1 Se1' C3 C4 -1.0(13) . . . . ?
C1 Se1' C3 C2 4(4) . . . . ?
C2 C3 C4 C2' -5(3) . . . . ?
Se1' C3 C4 C2' -3(3) . . . . ?
C2 C3 C4 Se1 -1.9(17) . . . . ?
Se1' C3 C4 Se1 -0.3(16) . . . . ?
C1 C2' C4 C3 7(5) . . . . ?
C1 C2' C4 Se1 -164(13) . . . . ?
C1 Se1 C4 C3 1.4(9) . . . . ?
C1 Se1 C4 C2' 11(9) . . . . ?
Se2 C5 C6 C7 1.4(10) . . . . ?
Bi1 C5 C6 C7 172.5(6) . . . . ?
C6 C5 Se2 C8 -0.4(6) . . . . ?
Bi1 C5 Se2 C8 -172.6(5) . . . . ?
C5 C6 C7 C8 -2.0(13) . . . . ?
C6 C7 C8 Se2 1.6(12) . . . . ?
C5 Se2 C8 C7 -0.7(8) . . . . ?
Se3 C9 C10 C11 -0.3(10) . . . . ?
Bi1 C9 C10 C11 179.0(6) . . . . ?
C9 C10 C11 C12 -0.4(12) . . . . ?
C10 C11 C12 Se3 0.9(10) . . . . ?
C11 C12 Se3 C9 -0.9(7) . . . . ?
C10 C9 Se3 C12 0.6(7) . . . . ?
Bi1 C9 Se3 C12 -178.7(5) . . . . ?

_refine_diff_density_max         2.246
_refine_diff_density_min         -1.972
_refine_diff_density_rms         0.292

_shelxl_version_number           2013-4


# start Validation Reply Form
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Residual Density  1.02A From     Bi1       2.73 eA-3  
RESPONSE: 
The highest unrefined electron density peaks (Q peaks) are located at:
1.04 A from Bi1 (Q1, 2.2 e A-3),
1.02 A from Bi1 (Q2, 2.2 e A-3),
0.85 A from Bi1 (Q3, 1.7 e A-3) and
0.96 A from Bi1 (Q4, 1.6 e A-3).

Acoording to W. Massa (Kristallstrukturbestimmung, Teubner Studienbuecher, 
Stuttgart, 1996) and W. Clegg (Crystal Structure Determination, Oxford 
University Press, 1998) this might be observed for heavy atoms for which 
remaining density peaks with ca. 10% of the electron density of the heavy 
atom are expected at distances between 0.6 and 1.2 A - and thus accounts
for Q1-Q4. 
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1541503'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H33 Bi S3 Si3'
_chemical_formula_sum            'C21 H33 Bi S3 Si3'
_chemical_formula_weight         674.90

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   41.799(3)
_cell_length_b                   6.3123(6)
_cell_length_c                   10.6006(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2797.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120
_cell_measurement_reflns_used    4181
_cell_measurement_theta_min      3.3590
_cell_measurement_theta_max      27.0580

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    6.663
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.41407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9017
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.371
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4827
_reflns_number_gt                3917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.954

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.001(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4827
_refine_ls_number_parameters     253
_refine_ls_number_restraints     125
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3497(4) 0.500(2) 0.2769(15) 0.027(3) Uani 1 1 d . U . . .
C2 C 0.3434(3) 0.373(2) 0.3845(14) 0.024(3) Uani 1 1 d . U . . .
H2 H 0.3579 0.2744 0.4156 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3129(4) 0.409(2) 0.4408(14) 0.030(4) Uani 1 1 d . . . . .
H3 H 0.3056 0.3373 0.5121 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2952(4) 0.562(3) 0.3772(14) 0.031(4) Uani 1 1 d . . . . .
C5 C 0.2435(4) 0.547(2) 0.5764(15) 0.029(3) Uani 1 1 d . . . . .
H5A H 0.2431 0.3952 0.5715 0.043 Uiso 1 1 calc R U . . .
H5B H 0.2227 0.5980 0.6001 0.043 Uiso 1 1 calc R U . . .
H5C H 0.2589 0.5904 0.6384 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2554(5) 0.955(3) 0.4320(19) 0.043(4) Uani 1 1 d . . . . .
H6A H 0.2702 0.9966 0.4964 0.065 Uiso 1 1 calc R U . . .
H6B H 0.2344 1.0055 0.4532 0.065 Uiso 1 1 calc R U . . .
H6C H 0.2618 1.0145 0.3526 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2264(4) 0.572(2) 0.2950(15) 0.030(4) Uani 1 1 d . . . . .
H7A H 0.2263 0.4206 0.2901 0.045 Uiso 1 1 calc R U . . .
H7B H 0.2329 0.6303 0.2153 0.045 Uiso 1 1 calc R U . . .
H7C H 0.2053 0.6217 0.3150 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4200(3) 0.289(2) 0.2885(13) 0.024(3) Uani 1 1 d . U . . .
C9 C 0.4173(4) 0.082(2) 0.3095(15) 0.030(3) Uani 1 1 d . U . . .
H9 H 0.4026 -0.0019 0.2669 0.036 Uiso 1 1 calc R U . . .
C10 C 0.4391(4) -0.004(2) 0.4040(18) 0.034(4) Uani 1 1 d . . . . .
H10 H 0.4391 -0.1458 0.4279 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4594(3) 0.143(2) 0.4544(15) 0.024(3) Uani 1 1 d . . . . .
C12 C 0.4988(4) -0.178(3) 0.5959(19) 0.043(4) Uani 1 1 d . . . . .
H12A H 0.4798 -0.2432 0.6288 0.064 Uiso 1 1 calc R U . . .
H12B H 0.5160 -0.1980 0.6545 0.064 Uiso 1 1 calc R U . . .
H12C H 0.5042 -0.2430 0.5167 0.064 Uiso 1 1 calc R U . . .
C13 C 0.5287(4) 0.242(3) 0.5084(17) 0.040(4) Uani 1 1 d . . . . .
H13A H 0.5245 0.3900 0.4943 0.061 Uiso 1 1 calc R U . . .
H13B H 0.5346 0.1765 0.4302 0.061 Uiso 1 1 calc R U . . .
H13C H 0.5458 0.2272 0.5682 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4805(4) 0.238(3) 0.7279(14) 0.039(4) Uani 1 1 d . . . . .
H14A H 0.4613 0.1728 0.7597 0.058 Uiso 1 1 calc R U . . .
H14B H 0.4768 0.3865 0.7158 0.058 Uiso 1 1 calc R U . . .
H14C H 0.4976 0.2179 0.7872 0.058 Uiso 1 1 calc R U . . .
C15 C 0.3763(4) 0.216(2) 0.0513(13) 0.026(3) Uani 1 1 d . U . . .
C16 C 0.3492(4) 0.096(3) 0.0695(14) 0.031(3) Uani 1 1 d . U . . .
H16 H 0.3350 0.1200 0.1355 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3446(4) -0.068(3) -0.0210(14) 0.029(3) Uani 1 1 d . U . . .
H17 H 0.3276 -0.1629 -0.0164 0.035 Uiso 1 1 calc R U . . .
C18 C 0.3665(4) -0.077(2) -0.1131(14) 0.027(3) Uani 1 1 d . U . . .
C19 C 0.4091(4) -0.352(3) -0.2772(15) 0.033(4) Uani 1 1 d . . . . .
H19A H 0.4232 -0.2335 -0.2897 0.049 Uiso 1 1 calc R U . . .
H19B H 0.4098 -0.4422 -0.3500 0.049 Uiso 1 1 calc R U . . .
H19C H 0.4158 -0.4301 -0.2042 0.049 Uiso 1 1 calc R U . . .
C20 C 0.3561(5) -0.094(3) -0.3952(15) 0.046(5) Uani 1 1 d . . . . .
H20A H 0.3717 0.0156 -0.4085 0.069 Uiso 1 1 calc R U . . .
H20B H 0.3355 -0.0316 -0.3816 0.069 Uiso 1 1 calc R U . . .
H20C H 0.3553 -0.1844 -0.4680 0.069 Uiso 1 1 calc R U . . .
C21 C 0.3380(4) -0.464(2) -0.2287(15) 0.031(4) Uani 1 1 d . . . . .
H21A H 0.3172 -0.4018 -0.2186 0.046 Uiso 1 1 calc R U . . .
H21B H 0.3434 -0.5426 -0.1541 0.046 Uiso 1 1 calc R U . . .
H21C H 0.3378 -0.5575 -0.3001 0.046 Uiso 1 1 calc R U . . .
Si1 Si 0.25467(9) 0.6589(6) 0.4195(4) 0.0238(9) Uani 1 1 d . . . . .
Si2 Si 0.49166(10) 0.1116(7) 0.5718(4) 0.0250(9) Uani 1 1 d . . . . .
Si3 Si 0.36766(11) -0.2541(7) -0.2537(4) 0.0276(9) Uani 1 1 d . . . . .
S1 S 0.31728(9) 0.6565(6) 0.2527(4) 0.0309(9) Uani 1 1 d . U . . .
S2 S 0.45016(9) 0.3878(6) 0.3862(4) 0.0264(8) Uani 1 1 d . U . . .
S3 S 0.39482(8) 0.1199(6) -0.0829(4) 0.0268(8) Uani 1 1 d . . . . .
Bi1 Bi 0.39302(2) 0.49564(8) 0.15717(15) 0.02334(19) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.42(2) . ?
C1 S1 1.696(15) . ?
C1 Bi1 2.211(16) . ?
C2 C3 1.43(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.39(2) . ?
C3 H3 0.9300 . ?
C4 S1 1.719(15) . ?
C4 Si1 1.855(17) . ?
C5 Si1 1.866(15) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 Si1 1.874(17) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 Si1 1.854(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.33(2) . ?
C8 S2 1.745(14) . ?
C8 Bi1 2.217(14) . ?
C9 C10 1.46(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.37(2) . ?
C10 H10 0.9300 . ?
C11 S2 1.750(13) . ?
C11 Si2 1.845(15) . ?
C12 Si2 1.873(17) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 Si2 1.878(17) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 Si2 1.895(16) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.38(2) . ?
C15 S3 1.729(15) . ?
C15 Bi1 2.206(15) . ?
C16 C17 1.42(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.34(2) . ?
C17 H17 0.9300 . ?
C18 S3 1.744(16) . ?
C18 Si3 1.865(16) . ?
C19 Si3 1.857(15) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 Si3 1.871(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 Si3 1.835(16) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 107.5(12) . . ?
C2 C1 Bi1 127.3(10) . . ?
S1 C1 Bi1 125.1(8) . . ?
C1 C2 C3 114.4(13) . . ?
C1 C2 H2 122.8 . . ?
C3 C2 H2 122.8 . . ?
C4 C3 C2 112.5(13) . . ?
C4 C3 H3 123.8 . . ?
C2 C3 H3 123.8 . . ?
C3 C4 S1 109.1(12) . . ?
C3 C4 Si1 126.7(12) . . ?
S1 C4 Si1 124.2(10) . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S2 108.2(11) . . ?
C9 C8 Bi1 129.8(11) . . ?
S2 C8 Bi1 122.0(7) . . ?
C8 C9 C10 115.4(14) . . ?
C8 C9 H9 122.3 . . ?
C10 C9 H9 122.3 . . ?
C11 C10 C9 113.8(13) . . ?
C11 C10 H10 123.1 . . ?
C9 C10 H10 123.1 . . ?
C10 C11 S2 107.4(11) . . ?
C10 C11 Si2 130.2(11) . . ?
S2 C11 Si2 122.4(8) . . ?
Si2 C12 H12A 109.5 . . ?
Si2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si2 C13 H13A 109.5 . . ?
Si2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si2 C14 H14A 109.5 . . ?
Si2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S3 106.9(11) . . ?
C16 C15 Bi1 129.1(11) . . ?
S3 C15 Bi1 123.9(9) . . ?
C15 C16 C17 114.6(14) . . ?
C15 C16 H16 122.7 . . ?
C17 C16 H16 122.7 . . ?
C18 C17 C16 115.4(14) . . ?
C18 C17 H17 122.3 . . ?
C16 C17 H17 122.3 . . ?
C17 C18 S3 107.5(12) . . ?
C17 C18 Si3 128.7(13) . . ?
S3 C18 Si3 123.8(9) . . ?
Si3 C19 H19A 109.5 . . ?
Si3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si3 C20 H20A 109.5 . . ?
Si3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si3 C21 H21A 109.5 . . ?
Si3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 Si1 C7 108.2(7) . . ?
C4 Si1 C5 108.6(7) . . ?
C7 Si1 C5 111.3(7) . . ?
C4 Si1 C6 109.4(8) . . ?
C7 Si1 C6 110.7(8) . . ?
C5 Si1 C6 108.6(8) . . ?
C11 Si2 C12 108.3(7) . . ?
C11 Si2 C13 108.2(7) . . ?
C12 Si2 C13 110.3(8) . . ?
C11 Si2 C14 111.3(7) . . ?
C12 Si2 C14 109.3(8) . . ?
C13 Si2 C14 109.4(8) . . ?
C21 Si3 C19 114.3(8) . . ?
C21 Si3 C18 107.5(7) . . ?
C19 Si3 C18 109.3(7) . . ?
C21 Si3 C20 109.4(8) . . ?
C19 Si3 C20 108.2(8) . . ?
C18 Si3 C20 108.1(7) . . ?
C1 S1 C4 96.4(8) . . ?
C8 S2 C11 95.2(7) . . ?
C15 S3 C18 95.6(8) . . ?
C15 Bi1 C1 92.5(6) . . ?
C15 Bi1 C8 90.6(5) . . ?
C1 Bi1 C8 93.7(5) . . ?

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
S1 C1 C2 C3 0.0(17) . . . . ?
Bi1 C1 C2 C3 -178.5(11) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 S1 -0.8(17) . . . . ?
C2 C3 C4 Si1 -179.1(11) . . . . ?
S2 C8 C9 C10 0.1(19) . . . . ?
Bi1 C8 C9 C10 -179.7(12) . . . . ?
C8 C9 C10 C11 -1(2) . . . . ?
C9 C10 C11 S2 1.8(19) . . . . ?
C9 C10 C11 Si2 -178.0(12) . . . . ?
S3 C15 C16 C17 1.3(16) . . . . ?
Bi1 C15 C16 C17 176.6(10) . . . . ?
C15 C16 C17 C18 -3(2) . . . . ?
C16 C17 C18 S3 2.4(17) . . . . ?
C16 C17 C18 Si3 -175.5(11) . . . . ?
C3 C4 Si1 C7 -112.6(14) . . . . ?
S1 C4 Si1 C7 69.4(11) . . . . ?
C3 C4 Si1 C5 8.4(16) . . . . ?
S1 C4 Si1 C5 -169.7(10) . . . . ?
C3 C4 Si1 C6 126.7(14) . . . . ?
S1 C4 Si1 C6 -51.3(12) . . . . ?
C10 C11 Si2 C12 10.7(19) . . . . ?
S2 C11 Si2 C12 -169.1(10) . . . . ?
C10 C11 Si2 C13 130.3(17) . . . . ?
S2 C11 Si2 C13 -49.5(12) . . . . ?
C10 C11 Si2 C14 -109.5(17) . . . . ?
S2 C11 Si2 C14 70.7(11) . . . . ?
C17 C18 Si3 C21 -13.0(16) . . . . ?
S3 C18 Si3 C21 169.4(9) . . . . ?
C17 C18 Si3 C19 -137.5(14) . . . . ?
S3 C18 Si3 C19 44.9(11) . . . . ?
C17 C18 Si3 C20 105.0(15) . . . . ?
S3 C18 Si3 C20 -72.6(11) . . . . ?
C2 C1 S1 C4 -0.4(12) . . . . ?
Bi1 C1 S1 C4 178.2(9) . . . . ?
C3 C4 S1 C1 0.8(12) . . . . ?
Si1 C4 S1 C1 179.1(10) . . . . ?
C9 C8 S2 C11 0.8(13) . . . . ?
Bi1 C8 S2 C11 -179.4(9) . . . . ?
C10 C11 S2 C8 -1.5(13) . . . . ?
Si2 C11 S2 C8 178.3(10) . . . . ?
C16 C15 S3 C18 0.0(11) . . . . ?
Bi1 C15 S3 C18 -175.6(8) . . . . ?
C17 C18 S3 C15 -1.4(12) . . . . ?
Si3 C18 S3 C15 176.7(9) . . . . ?

_refine_diff_density_max         2.563
_refine_diff_density_min         -1.670
_refine_diff_density_rms         0.196

_shelxl_version_number           2013-4


# start Validation Reply Form
_vrf_PLAT973_5                   
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PROBLEM: Check Calcd Positive Residual Density on     Bi1       1.66 eA-3  
RESPONSE: 

The highest unrefined electron density peaks (Q peaks) are located at:
1.12 A from Bi1 (Q1, 2.6 e A-3),
1.09 A from Bi1 (Q2, 2.5 e A-3),
1.06 A from Bi1 (Q3, 2.3 e A-3),
1.08 A from Bi1 (Q4, 2.3 e A-3),
1.15 A from Bi1 (Q5, 1.5 e A-3) and
1.03 A from Bi1 (Q6, 1.5 e A-3).

Acoording to W. Massa (Kristallstrukturbestimmung, Teubner Studienbuecher, 
Stuttgart, 1996) and W. Clegg (Crystal Structure Determination, Oxford 
University Press, 1998) this might be observed for heavy atoms for which 
remaining density peaks with ca. 10% of the electron density of the heavy 
atom are expected at distances between 0.6 and 1.2 A - and accounts
for Q1-Q4. The Q5 and Q6 peak, respectively, should correspond 
to usually observed unrefined electron density peaks.

;
# end Validation Reply Form
