# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2022

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

data_s5791l_auto
_database_code_depnum_ccdc_archive 'CCDC 2126590'
loop_
_audit_author_name
_audit_author_address
'Lili Li'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2022-08-03 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H6 Bi O8, C2 H8 N, 1.5(C3 H7 N O)'
_chemical_formula_sum            'C22.50 H24.50 Bi N2.50 O9.50'
_chemical_formula_weight         690.92
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     jek107
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.9161(5)
_cell_length_b                   10.14340(10)
_cell_length_c                   22.2019(4)
_cell_angle_alpha                90
_cell_angle_beta                 123.381(3)
_cell_angle_gamma                90
_cell_volume                     4873.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10831
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      75.9450
_cell_measurement_theta_min      4.7790
_shelx_estimated_absorpt_T_max   0.757
_shelx_estimated_absorpt_T_min   0.157
_exptl_absorpt_coefficient_mu    14.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15224
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.255
_diffrn_reflns_theta_min         4.849
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    103.00 130.00   1.00    1.00    --   43.42  30.00-180.00   27
  2  ω     58.00  85.00   1.00    1.00    --   43.42  30.00-180.00   27
  3  ω    -46.00 109.00   1.00    1.00    --   43.42  60.00  90.00  155
  4  ω     82.00 135.00   1.00    1.00    --   45.98  60.00 120.00   53
  5  ω     73.00 135.00   1.00    1.00    --   45.98  60.00-180.00   62
  6  ω     97.00 135.00   1.00    1.00    --   45.98  60.00-120.00   38
  7  ω     85.00 197.00   1.00    1.00    --  108.20  50.00-180.00  112
  8  ω     19.00  54.00   1.00    1.00    --  108.20  50.00 150.00   35
  9  ω     97.00 165.00   1.00    1.00    --  108.20  50.00-150.00   68
 10  ω     30.00  56.00   1.00    1.00    --  108.20  50.00-180.00   26
 11  ω     98.00 197.00   1.00    1.00    --  108.20  50.00  60.00   99
 12  ω     20.00 198.00   1.00    1.00    --  108.20   0.00-180.00  178
 13  ω    146.00 180.00   1.00    1.00    --  108.20  50.00  90.00   34
 14  ω    143.00 168.00   1.00    1.00    --  108.20  50.00 120.00   25
 15  ω    103.00 128.00   1.00    1.00    --  108.20  50.00 120.00   25
 16  ω    104.00 131.00   1.00    1.00    --  108.20  50.00  90.00   27
 17  ω    122.00 165.00   1.00    1.00    --  108.20  50.00 150.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0414366000
_diffrn_orient_matrix_UB_12      0.1222006000
_diffrn_orient_matrix_UB_13      0.0184591000
_diffrn_orient_matrix_UB_21      -0.0549077000
_diffrn_orient_matrix_UB_22      0.0900727000
_diffrn_orient_matrix_UB_23      -0.0190174000
_diffrn_orient_matrix_UB_31      0.0183742000
_diffrn_orient_matrix_UB_32      -0.0068403000
_diffrn_orient_matrix_UB_33      0.0787140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4598
_reflns_number_total             4842
_reflns_odcompleteness_completeness 97.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         2.114
_refine_diff_density_min         -2.572
_refine_diff_density_rms         0.196
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²+38.2482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N8S-C10S \\sim N8S-C9S \\sim N3S-C4S \\sim N3S-C5S
 with sigma of 0.02
 C4S-C2S \\sim C2S-C5S
 with sigma of 0.02
3. Restrained planarity
 N3S, O1S, C2S, C4S, C5S
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C5S \\sim C4S \\sim N3S \\sim C2S \\sim O1S: within 2A with sigma of 0.002 and
sigma for terminal atoms of 0.004 within 2A
5. Rigid body (RIGU) restrains
 O6S, N8S, C7S, C9S, C10S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C4S, O1S, C2S, N3S, C5S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Fixed Sof: O1S(0.5) N3S(0.5) C4S(0.5) H4SA(0.5) H4SB(0.5) H4SC(0.5) C2S(0.5)
 H2S(0.5) C5S(0.5) H5SA(0.5) H5SB(0.5) H5SC(0.5)
7.a Secondary CH2 refined with riding coordinates:
 N1D(H1DA,H1DB)
7.b Me refined with riding coordinates:
 C9S(H9SA,H9SB,H9SC), C10S(H10A,H10B,H10C), C4S(H4SA,H4SB,H4SC), C5S(H5SA,H5SB,
 H5SC)
7.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C14(H14), C10(H10), C16(H16), C12(H12), C7S(H7S), C2S(H2S)
7.d Idealised Me refined as rotating group:
 C2D(H2DA,H2DB,H2DC), C3D(H3DA,H3DB,H3DC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.08414(2) -0.12422(2) 0.53858(2) 0.01834(11) Uani 1 1 d . . . . .
O2 O 0.17887(17) -0.0605(4) 0.5667(2) 0.0267(8) Uani 1 1 d . . . . .
O3 O 0.35037(16) 0.2429(4) 0.86287(19) 0.0215(7) Uani 1 1 d . . . . .
O5 O 0.39238(18) -0.2290(4) 0.5211(2) 0.0251(8) Uani 1 1 d . . . . .
O4 O 0.42386(16) 0.3225(4) 0.85110(19) 0.0233(8) Uani 1 1 d . . . . .
O8 O 0.45614(18) 0.3574(4) 0.4907(2) 0.0213(7) Uani 1 1 d . . . . .
O1 O 0.16473(16) 0.0327(4) 0.6464(2) 0.0243(8) Uani 1 1 d . . . . .
O6 O 0.4557(2) -0.1374(4) 0.4967(3) 0.0276(9) Uani 1 1 d . . . . .
O7 O 0.4374(3) 0.4692(4) 0.5622(3) 0.0407(11) Uani 1 1 d . . . . .
C2 C 0.3756(2) 0.2575(5) 0.8273(3) 0.0198(10) Uani 1 1 d . . . . .
C1 C 0.1981(2) 0.0109(5) 0.6231(3) 0.0188(9) Uani 1 1 d . . . . .
C5 C 0.2604(2) 0.0711(5) 0.6577(3) 0.0198(10) Uani 1 1 d . . . . .
C6 C 0.2872(2) 0.1340(5) 0.7242(3) 0.0185(10) Uani 1 1 d . . . . .
H6 H 0.266003 0.137486 0.747955 0.022 Uiso 1 1 calc R U . . .
C8 C 0.3758(2) 0.1889(5) 0.7195(3) 0.0192(9) Uani 1 1 d . . . . .
H8 H 0.414694 0.231341 0.740202 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3496(3) 0.1246(5) 0.6538(3) 0.0215(11) Uani 1 1 d . . . . .
C4 C 0.4419(3) 0.3621(5) 0.5365(3) 0.0216(11) Uani 1 1 d . . . . .
C3 C 0.4226(3) -0.1288(5) 0.5212(3) 0.0207(11) Uani 1 1 d . . . . .
C7 C 0.3453(2) 0.1917(5) 0.7556(3) 0.0200(10) Uani 1 1 d . . . . .
C11 C 0.3813(3) 0.1214(5) 0.6143(3) 0.0206(11) Uani 1 1 d . . . . .
C14 C 0.4375(3) 0.1146(5) 0.5374(3) 0.0200(11) Uani 1 1 d . . . . .
H14 H 0.457958 0.111708 0.512755 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2926(2) 0.0647(5) 0.6241(3) 0.0200(10) Uani 1 1 d . . . . .
H10 H 0.275109 0.018190 0.579855 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4168(2) -0.0012(6) 0.5506(3) 0.0222(11) Uani 1 1 d . . . . .
C15 C 0.4284(2) 0.2335(5) 0.5601(3) 0.0189(10) Uani 1 1 d . . . . .
C16 C 0.4013(2) 0.2381(5) 0.5999(3) 0.0206(10) Uani 1 1 d . . . . .
H16 H 0.396529 0.320013 0.617055 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3881(2) 0.0026(5) 0.5883(3) 0.0214(10) Uani 1 1 d . . . . .
H12 H 0.373144 -0.076523 0.596308 0.026 Uiso 1 1 calc R U . . .
N1D N 0.3927(3) -0.2094(7) 0.8580(3) 0.0542(17) Uani 1 1 d . . . . .
H1DA H 0.419245 -0.244113 0.902590 0.065 Uiso 1 1 calc R U . . .
H1DB H 0.378347 -0.275767 0.825029 0.065 Uiso 1 1 calc R U . . .
N8S N 0.2881(4) -0.4379(8) 0.6257(4) 0.0635(18) Uani 1 1 d D . . . .
O6S O 0.3336(6) -0.3114(10) 0.7249(4) 0.131(5) Uani 1 1 d . . . . .
C2D C 0.3386(5) -0.1401(8) 0.8553(6) 0.055(2) Uani 1 1 d . . . . .
H2DA H 0.304481 -0.127482 0.804933 0.082 Uiso 1 1 calc R U . . .
H2DB H 0.352306 -0.054150 0.879239 0.082 Uiso 1 1 calc R U . . .
H2DC H 0.324467 -0.194468 0.880055 0.082 Uiso 1 1 calc R U . . .
C3D C 0.4237(5) -0.1106(11) 0.8417(6) 0.077(3) Uani 1 1 d . . . . .
H3DA H 0.393949 -0.070187 0.794905 0.115 Uiso 1 1 calc R U . . .
H3DB H 0.456945 -0.152217 0.839924 0.115 Uiso 1 1 calc R U . . .
H3DC H 0.441120 -0.042627 0.879266 0.115 Uiso 1 1 calc R U . . .
O1S O 0.5088(12) -0.333(2) 0.6217(11) 0.132(5) Uani 0.5 1 d . U P A -1
C7S C 0.3144(6) -0.4179(12) 0.6956(5) 0.075(3) Uani 1 1 d . . . . .
H7S H 0.318562 -0.491042 0.724698 0.090 Uiso 1 1 calc R U . . .
C9S C 0.2759(7) -0.3400(13) 0.5748(6) 0.092(4) Uani 1 1 d D . . . .
H9SA H 0.256186 -0.380108 0.526835 0.137 Uiso 1 1 calc R U . . .
H9SB H 0.248202 -0.273642 0.574330 0.137 Uiso 1 1 calc R U . . .
H9SC H 0.314713 -0.298064 0.587580 0.137 Uiso 1 1 calc R U . . .
C10S C 0.2638(5) -0.5650(10) 0.5917(6) 0.082(3) Uani 1 1 d D . . . .
H10A H 0.246448 -0.557942 0.539896 0.123 Uiso 1 1 calc R U . . .
H10B H 0.297200 -0.630298 0.613181 0.123 Uiso 1 1 calc R U . . .
H10C H 0.231416 -0.592661 0.599012 0.123 Uiso 1 1 calc R U . . .
N3S N 0.4971(11) -0.3831(18) 0.7154(11) 0.135(5) Uani 0.5 1 d D U P A -1
C4S C 0.4599(15) -0.273(3) 0.7067(15) 0.129(5) Uani 0.5 1 d D U P A -1
H4SA H 0.449609 -0.276173 0.743055 0.193 Uiso 0.5 1 calc R U P A -1
H4SB H 0.482499 -0.191326 0.712553 0.193 Uiso 0.5 1 calc R U P A -1
H4SC H 0.421721 -0.274879 0.658388 0.193 Uiso 0.5 1 calc R U P A -1
C2S C 0.5208(13) -0.410(3) 0.6714(13) 0.135(5) Uani 0.5 1 d D U P A -1
H2S H 0.545411 -0.486148 0.680200 0.162 Uiso 0.5 1 calc R U P A -1
C5S C 0.508(2) -0.467(3) 0.7738(15) 0.140(6) Uani 0.5 1 d D U P A -1
H5SA H 0.534172 -0.541949 0.778066 0.210 Uiso 0.5 1 calc R U P A -1
H5SB H 0.529645 -0.417022 0.818959 0.210 Uiso 0.5 1 calc R U P A -1
H5SC H 0.468900 -0.500048 0.764100 0.210 Uiso 0.5 1 calc R U P A -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 O2 2.269(3) . ?
Bi1 O3 2.324(3) 4_546 ?
Bi1 O5 2.287(4) 7_546 ?
Bi1 O4 2.625(4) 4_546 ?
Bi1 O1 2.668(4) . ?
Bi1 O6 2.576(4) 7_546 ?
Bi1 O7 2.533(4) 7_556 ?
Bi1 C2 2.825(5) 4_546 ?
Bi1 C1 2.832(5) . ?
Bi1 C3 2.794(5) 7_546 ?
O2 C1 1.286(6) . ?
O3 C2 1.281(6) . ?
O5 C3 1.282(6) . ?
O4 C2 1.246(6) . ?
O8 C4 1.259(7) . ?
O1 C1 1.247(6) . ?
O6 C3 1.245(7) . ?
O7 C4 1.263(7) . ?
C2 C7 1.489(7) . ?
C1 C5 1.485(6) . ?
C5 C6 1.393(7) . ?
C5 C10 1.395(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(7) . ?
C8 C7 1.401(6) . ?
C9 C11 1.495(8) . ?
C9 C10 1.383(8) . ?
C4 C15 1.516(7) . ?
C3 C13 1.495(8) . ?
C11 C16 1.398(7) . ?
C11 C12 1.389(7) . ?
C14 H14 0.9500 . ?
C14 C13 1.388(7) . ?
C14 C15 1.376(7) . ?
C10 H10 0.9500 . ?
C13 C12 1.392(7) . ?
C15 C16 1.402(7) . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?
N1D H1DA 0.9100 . ?
N1D H1DB 0.9100 . ?
N1D C2D 1.540(12) . ?
N1D C3D 1.450(12) . ?
N8S C7S 1.323(12) . ?
N8S C9S 1.404(11) . ?
N8S C10S 1.451(11) . ?
O6S C7S 1.218(14) . ?
C2D H2DA 0.9800 . ?
C2D H2DB 0.9800 . ?
C2D H2DC 0.9800 . ?
C3D H3DA 0.9800 . ?
C3D H3DB 0.9800 . ?
C3D H3DC 0.9800 . ?
O1S C2S 1.25(3) . ?
C7S H7S 0.9500 . ?
C9S H9SA 0.9800 . ?
C9S H9SB 0.9800 . ?
C9S H9SC 0.9800 . ?
C10S H10A 0.9800 . ?
C10S H10B 0.9800 . ?
C10S H10C 0.9800 . ?
N3S C4S 1.420(17) . ?
N3S C2S 1.44(4) . ?
N3S C5S 1.443(16) . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
C2S H2S 0.9500 . ?
C5S H5SA 0.9800 . ?
C5S H5SB 0.9800 . ?
C5S H5SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Bi1 O3 77.71(14) . 4_546 ?
O2 Bi1 O5 75.65(13) . 7_546 ?
O2 Bi1 O4 115.53(12) . 4_546 ?
O2 Bi1 O1 52.34(12) . . ?
O2 Bi1 O6 122.87(14) . 7_546 ?
O2 Bi1 O7 75.22(16) . 7_556 ?
O2 Bi1 C2 96.59(14) . 4_546 ?
O2 Bi1 C1 26.36(14) . . ?
O2 Bi1 C3 99.28(15) . 7_546 ?
O3 Bi1 O4 52.68(11) 4_546 4_546 ?
O3 Bi1 O1 72.29(14) 4_546 . ?
O3 Bi1 O6 72.82(14) 4_546 7_546 ?
O3 Bi1 O7 152.08(15) 4_546 7_556 ?
O3 Bi1 C2 26.61(13) 4_546 4_546 ?
O3 Bi1 C1 72.66(14) 4_546 . ?
O3 Bi1 C3 75.48(15) 4_546 7_546 ?
O5 Bi1 O3 83.01(14) 7_546 4_546 ?
O5 Bi1 O4 126.09(13) 7_546 4_546 ?
O5 Bi1 O1 125.54(12) 7_546 . ?
O5 Bi1 O6 53.30(12) 7_546 7_546 ?
O5 Bi1 O7 83.80(14) 7_546 7_556 ?
O5 Bi1 C2 105.81(14) 7_546 4_546 ?
O5 Bi1 C1 100.71(14) 7_546 . ?
O5 Bi1 C3 26.92(14) 7_546 7_546 ?
O4 Bi1 O1 73.19(12) 4_546 . ?
O4 Bi1 C2 26.09(13) 4_546 4_546 ?
O4 Bi1 C1 94.04(13) 4_546 . ?
O4 Bi1 C3 104.00(14) 4_546 7_546 ?
O1 Bi1 C2 69.81(13) . 4_546 ?
O1 Bi1 C1 25.99(12) . . ?
O1 Bi1 C3 140.69(14) . 7_546 ?
O6 Bi1 O4 82.33(13) 7_546 4_546 ?
O6 Bi1 O1 144.83(14) 7_546 . ?
O6 Bi1 C2 77.05(15) 7_546 4_546 ?
O6 Bi1 C1 138.85(14) 7_546 . ?
O6 Bi1 C3 26.41(14) 7_546 7_546 ?
O7 Bi1 O4 149.30(13) 7_556 4_546 ?
O7 Bi1 O1 96.03(14) 7_556 . ?
O7 Bi1 O6 117.22(15) 7_556 7_546 ?
O7 Bi1 C2 165.70(16) 7_556 4_546 ?
O7 Bi1 C1 85.81(16) 7_556 . ?
O7 Bi1 C3 102.20(15) 7_556 7_546 ?
C2 Bi1 C1 82.03(14) 4_546 . ?
C3 Bi1 C2 90.58(15) 7_546 4_546 ?
C3 Bi1 C1 121.20(15) 7_546 . ?
C1 O2 Bi1 102.1(3) . . ?
C2 O3 Bi1 99.1(3) . 4_556 ?
C3 O5 Bi1 99.2(3) . 7_546 ?
C2 O4 Bi1 85.9(3) . 4_556 ?
C1 O1 Bi1 84.4(3) . . ?
C3 O6 Bi1 86.6(3) . 7_546 ?
C4 O7 Bi1 99.5(3) . 7_556 ?
O3 C2 Bi1 54.3(2) . 4_556 ?
O3 C2 C7 117.4(4) . . ?
O4 C2 Bi1 68.0(3) . 4_556 ?
O4 C2 O3 122.2(4) . . ?
O4 C2 C7 120.4(4) . . ?
C7 C2 Bi1 171.3(3) . 4_556 ?
O2 C1 Bi1 51.6(2) . . ?
O2 C1 C5 117.6(4) . . ?
O1 C1 Bi1 69.7(3) . . ?
O1 C1 O2 121.2(4) . . ?
O1 C1 C5 121.1(4) . . ?
C5 C1 Bi1 169.2(3) . . ?
C6 C5 C1 120.2(4) . . ?
C6 C5 C10 119.4(5) . . ?
C10 C5 C1 120.4(4) . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.7(5) . . ?
C7 C6 H6 120.1 . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.5(5) . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C11 121.2(5) . . ?
C10 C9 C8 118.9(5) . . ?
C10 C9 C11 119.9(5) . . ?
O8 C4 O7 122.6(5) . . ?
O8 C4 C15 118.2(5) . . ?
O7 C4 C15 119.2(5) . . ?
O5 C3 Bi1 53.9(2) . 7_546 ?
O5 C3 C13 118.6(5) . . ?
O6 C3 Bi1 67.0(3) . 7_546 ?
O6 C3 O5 120.7(5) . . ?
O6 C3 C13 120.7(5) . . ?
C13 C3 Bi1 171.4(4) . 7_546 ?
C6 C7 C2 120.8(4) . . ?
C6 C7 C8 119.9(5) . . ?
C8 C7 C2 119.3(4) . . ?
C16 C11 C9 120.5(4) . . ?
C12 C11 C9 119.9(4) . . ?
C12 C11 C16 119.4(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.1(5) . . ?
C5 C10 H10 119.3 . . ?
C9 C10 C5 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
C14 C13 C3 119.8(5) . . ?
C14 C13 C12 119.9(5) . . ?
C12 C13 C3 120.2(5) . . ?
C14 C15 C4 120.7(5) . . ?
C14 C15 C16 120.3(5) . . ?
C16 C15 C4 118.7(5) . . ?
C11 C16 C15 119.7(5) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
H1DA N1D H1DB 108.6 . . ?
C2D N1D H1DA 110.3 . . ?
C2D N1D H1DB 110.3 . . ?
C3D N1D H1DA 110.3 . . ?
C3D N1D H1DB 110.3 . . ?
C3D N1D C2D 107.0(8) . . ?
C7S N8S C9S 125.3(10) . . ?
C7S N8S C10S 122.9(9) . . ?
C9S N8S C10S 111.6(9) . . ?
N1D C2D H2DA 109.5 . . ?
N1D C2D H2DB 109.5 . . ?
N1D C2D H2DC 109.5 . . ?
H2DA C2D H2DB 109.5 . . ?
H2DA C2D H2DC 109.5 . . ?
H2DB C2D H2DC 109.5 . . ?
N1D C3D H3DA 109.5 . . ?
N1D C3D H3DB 109.5 . . ?
N1D C3D H3DC 109.5 . . ?
H3DA C3D H3DB 109.5 . . ?
H3DA C3D H3DC 109.5 . . ?
H3DB C3D H3DC 109.5 . . ?
N8S C7S H7S 118.0 . . ?
O6S C7S N8S 123.9(11) . . ?
O6S C7S H7S 118.0 . . ?
N8S C9S H9SA 109.5 . . ?
N8S C9S H9SB 109.5 . . ?
N8S C9S H9SC 109.5 . . ?
H9SA C9S H9SB 109.5 . . ?
H9SA C9S H9SC 109.5 . . ?
H9SB C9S H9SC 109.5 . . ?
N8S C10S H10A 109.5 . . ?
N8S C10S H10B 109.5 . . ?
N8S C10S H10C 109.5 . . ?
H10A C10S H10B 109.5 . . ?
H10A C10S H10C 109.5 . . ?
H10B C10S H10C 109.5 . . ?
C4S N3S C2S 124.8(15) . . ?
C4S N3S C5S 112(2) . . ?
C2S N3S C5S 123.2(16) . . ?
N3S C4S H4SA 109.5 . . ?
N3S C4S H4SB 109.5 . . ?
N3S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
O1S C2S N3S 119(3) . . ?
O1S C2S H2S 120.3 . . ?
N3S C2S H2S 120.3 . . ?
N3S C5S H5SA 109.5 . . ?
N3S C5S H5SB 109.5 . . ?
N3S C5S H5SC 109.5 . . ?
H5SA C5S H5SB 109.5 . . ?
H5SA C5S H5SC 109.5 . . ?
H5SB C5S H5SC 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.791
_oxdiff_exptl_absorpt_empirical_full_min 0.525
####################################################################### 
# 
# 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_s5795r
_database_code_depnum_ccdc_archive 'CCDC 2126600'
loop_
_audit_author_name
_audit_author_address
'Lili Li'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-12-06 deposited with the CCDC.	2022-08-03 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H23 Bi2 N O18'
_chemical_formula_sum            'C35 H23 Bi2 N O18'
_chemical_formula_weight         1163.50
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I  a '
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   19.0988(4)
_cell_length_b                   7.2639(2)
_cell_length_c                   23.0662(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.885(2)
_cell_angle_gamma                90
_cell_volume                     3142.44(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5712
_cell_measurement_temperature    100.02(12)
_cell_measurement_theta_max      75.2880
_cell_measurement_theta_min      3.8880
_shelx_estimated_absorpt_T_max   0.806
_shelx_estimated_absorpt_T_min   0.398
_exptl_absorpt_coefficient_mu    22.582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11261
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.052
_diffrn_reflns_theta_min         3.903
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  13.00   1.00    1.00    --  -44.94  38.00-180.00   30
  2  ω    -39.00  33.00   1.00    1.00    --  -46.66   0.00  60.00   72
  3  ω   -136.00 -45.00   1.00    1.00    --  -46.66   0.00  60.00   91
  4  ω    -78.00 -17.00   1.00    1.00    --  -46.66  57.00 -60.00   61
  5  ω   -170.00-110.00   1.00    1.50    -- -107.20 -76.00 120.00   60
  6  ω   -176.00 -68.00   1.00    1.50    -- -107.20 -76.00  60.00  108
  7  ω   -193.00-132.00   1.00    1.50    -- -107.20 -76.00  90.00   61
  8  ω    -55.00 -19.00   1.00    1.50    -- -107.20  76.00 -90.00   36
  9  ω   -107.00 -80.00   1.00    1.50    -- -107.20 -57.00 150.00   27
 10  ω    -84.00 -57.00   1.00    1.50    -- -107.20  76.00 -90.00   27
 11  ω   -197.00-170.00   1.00    1.50    -- -107.20 -76.00   0.00   27
 12  ω   -167.00 -69.00   1.00    1.50    -- -107.20 -76.00   0.00   98
 13  ω   -137.00 -53.00   1.00    1.50    -- -107.20  57.00   0.00   84
 14  ω   -143.00 -76.00   1.00    1.50    -- -107.20  76.00 -60.00   67
 15  ω   -143.00 -76.00   1.00    1.50    -- -107.20 -38.00  60.00   67
 16  ω   -147.00-121.00   1.00    1.50    -- -107.20  76.00 -90.00   26
 17  ω    -46.00 -21.00   1.00    1.50    -- -107.20  76.00 -60.00   25
 18  ω   -150.00-107.00   1.00    1.50    -- -107.20  19.00 -90.00   43
 19  ω    -46.00 -19.00   1.00    1.50    -- -107.20  19.00 -90.00   27
 20  ω   -112.00 -68.00   1.00    1.50    -- -107.20 -76.00-150.00   44
 21  ω   -109.00 -77.00   1.00    1.50    -- -107.20 -76.00  90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0117160000
_diffrn_orient_matrix_UB_12      -0.1386586000
_diffrn_orient_matrix_UB_13      -0.0478653000
_diffrn_orient_matrix_UB_21      0.0358914000
_diffrn_orient_matrix_UB_22      -0.1340979000
_diffrn_orient_matrix_UB_23      0.0483284000
_diffrn_orient_matrix_UB_31      -0.0729065000
_diffrn_orient_matrix_UB_32      -0.0881522000
_diffrn_orient_matrix_UB_33      0.0016605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4639
_reflns_number_total             4787
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         5.822
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.233
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.439(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     488
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²+37.1050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1104
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.561(19)
 0.439(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H17 of O17
 At 1.5 times of:
  All C(H,H,H) groups, H11 of O11, H8 of O8, H16 of O16
3. Uiso/Uaniso restraints and constraints
C4 \\sim C6 \\sim C7 \\sim C2 \\sim C3: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 2A
4. Rigid body (RIGU) restrains
 C26, Bi1, O17, O9, O1, O2, Bi2, C17, C1, O18, O10, C18, C2, C33, C19, C23, C7,
  C3, N34, C20, C22, C6, C4, C35, C36, C21, C24, C25, C9, C5, C8, O12, O11, C30,
  C14, C10, O4, O3, C27, C29, C13, C11, C28, C31, C32, C16, C12, C15, O14, O13,
 O16, O15, O7, O8, O6, O5
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5.a Riding coordinates:
 O11(H11), O16(H16)
5.b Me refined with riding coordinates:
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
5.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C14(H14), C28(H28), C10(H10), C30(H30), C21(H21), O17(H17),
 C19(H19), C23(H23), C12(H12), C7(H7), C5(H5), C3(H3), C33(H33)
5.d Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.50206(2) 0.38270(7) 0.52891(2) 0.02039(16) Uani 1 1 d . . . . .
Bi2 Bi 0.43908(3) 0.86299(8) 0.56093(2) 0.02578(18) Uani 1 1 d . . . . .
O12 O 0.5565(6) 0.7459(17) 0.9213(4) 0.029(2) Uani 1 1 d . . . . .
O6 O 0.0481(6) 0.5319(16) 0.0859(4) 0.025(2) Uani 1 1 d . . . . .
O9 O 0.5673(6) 0.4572(16) 0.6277(4) 0.0229(19) Uani 1 1 d . . . . .
O7 O 0.3153(6) 0.6844(17) 0.1078(5) 0.026(2) Uani 1 1 d . . . . .
C15 C 0.0570(8) 0.5331(19) 0.1423(6) 0.019(2) Uani 1 1 d . . . . .
O5 O 0.0073(6) 0.4887(16) 0.1666(4) 0.027(2) Uani 1 1 d . . . . .
C9 C 0.2031(9) 0.621(2) 0.2753(7) 0.021(3) Uani 1 1 d . . . . .
O1 O 0.4138(5) 0.4762(17) 0.4414(4) 0.026(2) Uani 1 1 d . . . . .
C25 C 0.7570(9) 0.617(2) 0.8120(7) 0.021(3) Uani 1 1 d . . . . .
C26 C 0.7874(7) 0.5510(19) 0.8681(6) 0.017(2) Uani 1 1 d . . . . .
H26 H 0.758126 0.497808 0.892677 0.021 Uiso 1 1 calc R U . . .
O14 O 0.9545(5) 0.5332(15) 0.9746(4) 0.025(2) Uani 1 1 d . . . . .
C14 C 0.2577(8) 0.677(2) 0.2462(6) 0.023(3) Uani 1 1 d . . . . .
H14 H 0.302322 0.710820 0.269476 0.028 Uiso 1 1 calc R U . . .
O11 O 0.4650(6) 0.8318(19) 0.8500(5) 0.033(2) Uani 1 1 d . . . . .
H11 H 0.447376 0.876578 0.877590 0.049 Uiso 1 1 d R U . . .
C11 C 0.1277(8) 0.583(2) 0.1788(6) 0.020(2) Uani 1 1 d . . . . .
C27 C 0.8636(8) 0.564(2) 0.8886(6) 0.022(2) Uani 1 1 d . . . . .
O18 O 0.3882(7) 1.1664(17) 0.5675(6) 0.040(3) Uani 1 1 d . . . . .
C17 C 0.5311(8) 0.540(2) 0.6605(6) 0.022(2) Uani 1 1 d . . . . .
O2 O 0.3769(5) 0.5397(16) 0.5241(4) 0.0243(18) Uani 1 1 d . . . . .
C20 C 0.5638(8) 0.692(2) 0.8220(6) 0.024(2) Uani 1 1 d . . . . .
C28 C 0.9047(9) 0.645(2) 0.8518(8) 0.027(3) Uani 1 1 d . . . . .
H28 H 0.954630 0.657390 0.865149 0.033 Uiso 1 1 calc R U . . .
C35 C 0.2270(10) 1.329(3) 0.6079(8) 0.034(3) Uani 1 1 d . . . . .
H35A H 0.176665 1.310548 0.590310 0.052 Uiso 1 1 calc R U . . .
H35B H 0.236689 1.277782 0.647914 0.052 Uiso 1 1 calc R U . . .
H35C H 0.237930 1.460822 0.609508 0.052 Uiso 1 1 calc R U . . .
O10 O 0.4656(6) 0.5861(16) 0.6416(4) 0.0250(19) Uani 1 1 d . . . . .
C10 C 0.1368(8) 0.5765(19) 0.2391(6) 0.020(2) Uani 1 1 d . . . . .
H10 H 0.097970 0.541011 0.256940 0.024 Uiso 1 1 calc R U . . .
O4 O 0.0462(6) 0.6558(15) 0.4375(4) 0.024(2) Uani 1 1 d . . . . .
C18 C 0.5690(8) 0.589(2) 0.7232(6) 0.020(2) Uani 1 1 d . . . . .
C29 C 0.8747(9) 0.706(2) 0.7970(7) 0.027(2) Uani 1 1 d . . . . .
C30 C 0.7998(9) 0.694(2) 0.7768(7) 0.027(3) Uani 1 1 d . . . . .
H30 H 0.779147 0.739536 0.738800 0.032 Uiso 1 1 calc R U . . .
C21 C 0.6367(8) 0.674(2) 0.8354(6) 0.021(2) Uani 1 1 d . . . . .
H21 H 0.660294 0.700446 0.874491 0.026 Uiso 1 1 calc R U . . .
O8 O 0.3590(6) 0.8365(17) 0.1914(4) 0.028(2) Uani 1 1 d . . . . .
H8 H 0.386328 0.881441 0.170567 0.041 Uiso 1 1 calc R U . . .
C31 C 0.8923(9) 0.496(2) 0.9478(7) 0.030(3) Uani 1 1 d . . . . .
O3 O 0.1225(6) 0.6291(16) 0.5209(5) 0.028(2) Uani 1 1 d . . . . .
O17 O 0.5169(5) 0.6792(14) 0.5249(5) 0.0225(17) Uani 1 1 d . . . . .
H17 H 0.554777 0.729972 0.508541 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2503(8) 0.684(2) 0.1862(6) 0.022(2) Uani 1 1 d . . . . .
C16 C 0.3104(8) 0.730(2) 0.1580(6) 0.022(2) Uani 1 1 d . . . . .
C19 C 0.5283(8) 0.653(2) 0.7637(7) 0.023(3) Uani 1 1 d . . . . .
H19 H 0.478254 0.669490 0.752337 0.028 Uiso 1 1 calc R U . . .
C23 C 0.6413(8) 0.571(2) 0.7381(6) 0.022(2) Uani 1 1 d . . . . .
H23 H 0.667254 0.526438 0.709750 0.026 Uiso 1 1 calc R U . . .
C12 C 0.1838(8) 0.6377(18) 0.1512(7) 0.020(2) Uani 1 1 d . . . . .
H12 H 0.177123 0.643203 0.109400 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2814(7) 0.563(2) 0.3724(6) 0.0194(14) Uani 1 1 d . U . . .
H7 H 0.319334 0.534206 0.352667 0.023 Uiso 1 1 calc R U . . .
N34 N 0.2696(8) 1.240(2) 0.5735(6) 0.036(3) Uani 1 1 d . . . . .
C22 C 0.6777(9) 0.618(2) 0.7948(7) 0.022(3) Uani 1 1 d . . . . .
O13 O 0.8529(8) 0.3943(19) 0.9726(6) 0.041(3) Uani 1 1 d . . . . .
C32 C 0.9235(14) 0.786(3) 0.7603(11) 0.054(4) Uani 1 1 d . . . . .
C24 C 0.5276(8) 0.760(2) 0.8690(6) 0.023(2) Uani 1 1 d . . . . .
C4 C 0.1702(7) 0.6308(18) 0.4304(6) 0.0171(16) Uani 1 1 d . U . . .
C2 C 0.2922(7) 0.559(2) 0.4337(6) 0.0187(14) Uani 1 1 d . U . . .
C1 C 0.3640(7) 0.523(2) 0.4683(6) 0.021(2) Uani 1 1 d . . . . .
C5 C 0.1578(8) 0.6419(19) 0.3705(6) 0.021(3) Uani 1 1 d . . . . .
H5 H 0.111363 0.670948 0.349488 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2133(8) 0.6106(19) 0.3395(6) 0.0184(16) Uani 1 1 d . U . . .
O16 O 0.8955(13) 0.877(3) 0.7168(9) 0.077(5) Uani 1 1 d . . . . .
H16 H 0.907382 0.901069 0.684444 0.116 Uiso 1 1 d R U . . .
C36 C 0.2328(14) 1.137(3) 0.5212(10) 0.047(4) Uani 1 1 d . . . . .
H36A H 0.181139 1.149954 0.517794 0.070 Uiso 1 1 calc R U . . .
H36B H 0.247194 1.185650 0.485665 0.070 Uiso 1 1 calc R U . . .
H36C H 0.245723 1.006149 0.525644 0.070 Uiso 1 1 calc R U . . .
O15 O 0.9879(9) 0.783(3) 0.7744(8) 0.065(4) Uani 1 1 d . . . . .
C8 C 0.1115(8) 0.644(2) 0.4644(7) 0.018(2) Uani 1 1 d . . . . .
C3 C 0.2367(7) 0.5921(19) 0.4643(6) 0.0181(14) Uani 1 1 d . U . . .
H3 H 0.244264 0.587999 0.506218 0.022 Uiso 1 1 calc R U . . .
C33 C 0.3421(10) 1.247(2) 0.5899(8) 0.037(3) Uani 1 1 d . . . . .
H33 H 0.359771 1.324191 0.622737 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O9 2.444(10) . ?
Bi1 O1 2.468(10) . ?
Bi1 O2 2.631(10) . ?
Bi1 O4 2.430(10) 2_565 ?
Bi1 O3 2.344(10) 2_565 ?
Bi1 O17 2.177(10) . ?
Bi1 C8 2.791(15) 2_565 ?
Bi2 O6 2.392(11) 3 ?
Bi2 O5 2.697(11) 3 ?
Bi2 O14 2.408(11) 3_454 ?
Bi2 O18 2.425(12) . ?
Bi2 O2 2.695(11) . ?
Bi2 O10 2.722(11) . ?
Bi2 C31 2.768(17) 3_454 ?
Bi2 O17 2.270(10) . ?
Bi2 O13 2.375(12) 3_454 ?
O12 C24 1.233(18) . ?
O6 C15 1.279(17) . ?
O9 C17 1.268(18) . ?
O7 C16 1.224(18) . ?
C15 O5 1.233(18) . ?
C15 C11 1.50(2) . ?
C9 C14 1.40(2) . ?
C9 C10 1.42(2) . ?
C9 C6 1.46(2) . ?
O1 C1 1.275(17) . ?
C25 C26 1.40(2) . ?
C25 C30 1.38(2) . ?
C25 C22 1.49(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.446(19) . ?
O14 C31 1.26(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.364(19) . ?
O11 H11 0.8399 . ?
O11 C24 1.302(19) . ?
C11 C10 1.368(19) . ?
C11 C12 1.40(2) . ?
C27 C28 1.39(2) . ?
C27 C31 1.46(2) . ?
O18 C33 1.25(2) . ?
C17 O10 1.288(19) . ?
C17 C18 1.532(19) . ?
O2 C1 1.269(17) . ?
C20 C21 1.37(2) . ?
C20 C19 1.42(2) . ?
C20 C24 1.474(19) . ?
C28 H28 0.9500 . ?
C28 C29 1.36(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C35 N34 1.40(2) . ?
C10 H10 0.9500 . ?
O4 C8 1.286(19) . ?
C18 C19 1.40(2) . ?
C18 C23 1.36(2) . ?
C29 C30 1.42(2) . ?
C29 C32 1.49(2) . ?
C30 H30 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.39(2) . ?
O8 H8 0.8400 . ?
O8 C16 1.336(19) . ?
C31 O13 1.27(2) . ?
O3 C8 1.283(19) . ?
O17 H17 0.9500 . ?
C13 C16 1.462(19) . ?
C13 C12 1.41(2) . ?
C19 H19 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.40(2) . ?
C12 H12 0.9500 . ?
C7 H7 0.9500 . ?
C7 C2 1.389(18) . ?
C7 C6 1.42(2) . ?
N34 C36 1.48(3) . ?
N34 C33 1.37(2) . ?
C32 O16 1.23(3) . ?
C32 O15 1.21(3) . ?
C4 C5 1.360(19) . ?
C4 C8 1.487(19) . ?
C4 C3 1.39(2) . ?
C2 C1 1.475(19) . ?
C2 C3 1.400(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(19) . ?
O16 H16 0.8401 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C3 H3 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O9 Bi1 O1 148.3(4) . . ?
O9 Bi1 O2 104.1(3) . . ?
O9 Bi1 C8 102.2(4) . 2_565 ?
O1 Bi1 O2 51.0(3) . . ?
O1 Bi1 C8 92.7(4) . 2_565 ?
O2 Bi1 C8 140.6(4) . 2_565 ?
O4 Bi1 O9 129.4(3) 2_565 . ?
O4 Bi1 O1 67.5(3) 2_565 . ?
O4 Bi1 O2 118.3(3) 2_565 . ?
O4 Bi1 C8 27.4(4) 2_565 2_565 ?
O3 Bi1 O9 75.3(4) 2_565 . ?
O3 Bi1 O1 118.3(4) 2_565 . ?
O3 Bi1 O2 155.4(4) 2_565 . ?
O3 Bi1 O4 54.6(4) 2_565 2_565 ?
O3 Bi1 C8 27.2(4) 2_565 2_565 ?
O17 Bi1 O9 76.9(4) . . ?
O17 Bi1 O1 76.5(4) . . ?
O17 Bi1 O2 72.2(4) . . ?
O17 Bi1 O4 90.4(4) . 2_565 ?
O17 Bi1 O3 84.0(4) . 2_565 ?
O17 Bi1 C8 85.9(4) . 2_565 ?
O6 Bi2 O5 50.1(3) 3 3 ?
O6 Bi2 O14 72.5(3) 3 3_454 ?
O6 Bi2 O18 81.9(4) 3 . ?
O6 Bi2 O2 146.6(3) 3 . ?
O6 Bi2 O10 100.0(3) 3 . ?
O6 Bi2 C31 99.2(4) 3 3_454 ?
O5 Bi2 O10 68.7(3) 3 . ?
O5 Bi2 C31 138.5(4) 3 3_454 ?
O14 Bi2 O5 117.4(3) 3_454 3 ?
O14 Bi2 O18 72.5(4) 3_454 . ?
O14 Bi2 O2 107.6(3) 3_454 . ?
O14 Bi2 O10 155.3(3) 3_454 . ?
O14 Bi2 C31 27.1(4) 3_454 3_454 ?
O18 Bi2 O5 76.5(4) . 3 ?
O18 Bi2 O2 130.8(4) . . ?
O18 Bi2 O10 130.8(4) . . ?
O18 Bi2 C31 71.4(5) . 3_454 ?
O2 Bi2 O5 133.5(3) . 3 ?
O2 Bi2 O10 65.6(3) . . ?
O2 Bi2 C31 87.8(4) . 3_454 ?
O10 Bi2 C31 152.6(4) . 3_454 ?
O17 Bi2 O6 77.8(4) . 3 ?
O17 Bi2 O5 107.0(4) . 3 ?
O17 Bi2 O14 78.9(4) . 3_454 ?
O17 Bi2 O18 148.8(4) . . ?
O17 Bi2 O2 69.6(3) . . ?
O17 Bi2 O10 76.5(3) . . ?
O17 Bi2 C31 88.7(5) . 3_454 ?
O17 Bi2 O13 97.9(5) . 3_454 ?
O13 Bi2 O6 126.0(4) 3_454 3 ?
O13 Bi2 O5 151.7(5) 3_454 3 ?
O13 Bi2 O14 54.2(4) 3_454 3_454 ?
O13 Bi2 O18 75.3(5) 3_454 . ?
O13 Bi2 O2 67.7(4) 3_454 . ?
O13 Bi2 O10 131.8(4) 3_454 . ?
O13 Bi2 C31 27.1(5) 3_454 3_454 ?
C15 O6 Bi2 101.0(9) . 3_444 ?
C17 O9 Bi1 114.9(9) . . ?
O6 C15 C11 120.4(13) . . ?
O5 C15 O6 119.7(14) . . ?
O5 C15 C11 119.9(12) . . ?
C15 O5 Bi2 87.7(8) . 3_444 ?
C14 C9 C10 116.5(13) . . ?
C14 C9 C6 122.2(14) . . ?
C10 C9 C6 121.3(14) . . ?
C1 O1 Bi1 97.6(8) . . ?
C26 C25 C22 118.2(15) . . ?
C30 C25 C26 119.7(15) . . ?
C30 C25 C22 121.8(16) . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.8(13) . . ?
C27 C26 H26 120.1 . . ?
C31 O14 Bi2 92.5(10) . 3_545 ?
C9 C14 H14 118.2 . . ?
C13 C14 C9 123.6(15) . . ?
C13 C14 H14 118.2 . . ?
C24 O11 H11 112.0 . . ?
C10 C11 C15 119.4(13) . . ?
C10 C11 C12 120.7(14) . . ?
C12 C11 C15 119.9(12) . . ?
C26 C27 C31 117.4(14) . . ?
C28 C27 C26 118.6(14) . . ?
C28 C27 C31 124.0(15) . . ?
C33 O18 Bi2 140.9(11) . . ?
O9 C17 O10 121.8(13) . . ?
O9 C17 C18 117.3(13) . . ?
O10 C17 C18 121.0(13) . . ?
Bi1 O2 Bi2 91.3(3) . . ?
C1 O2 Bi1 90.2(8) . . ?
C1 O2 Bi2 113.1(9) . . ?
C21 C20 C19 118.4(13) . . ?
C21 C20 C24 117.6(12) . . ?
C19 C20 C24 123.9(13) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.2(15) . . ?
C29 C28 H28 119.4 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N34 C35 H35A 109.5 . . ?
N34 C35 H35B 109.5 . . ?
N34 C35 H35C 109.5 . . ?
C17 O10 Bi2 117.7(9) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(14) . . ?
C11 C10 H10 119.4 . . ?
C8 O4 Bi1 92.1(8) . 2_465 ?
C19 C18 C17 118.9(13) . . ?
C23 C18 C17 119.5(13) . . ?
C23 C18 C19 121.6(13) . . ?
C28 C29 C30 120.4(14) . . ?
C28 C29 C32 117.2(17) . . ?
C30 C29 C32 122.4(17) . . ?
C25 C30 C29 120.3(15) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C20 C21 H21 118.2 . . ?
C20 C21 C22 123.7(14) . . ?
C22 C21 H21 118.2 . . ?
C16 O8 H8 109.5 . . ?
O14 C31 Bi2 60.4(8) . 3_545 ?
O14 C31 C27 122.6(16) . . ?
O14 C31 O13 119.2(15) . . ?
C27 C31 Bi2 176.8(12) . 3_545 ?
O13 C31 Bi2 58.9(8) . 3_545 ?
O13 C31 C27 118.1(15) . . ?
C8 O3 Bi1 96.2(9) . 2_465 ?
Bi1 O17 Bi2 117.8(4) . . ?
Bi1 O17 H17 121.1 . . ?
Bi2 O17 H17 121.1 . . ?
C14 C13 C16 121.4(14) . . ?
C14 C13 C12 118.7(14) . . ?
C12 C13 C16 119.8(13) . . ?
O7 C16 O8 122.2(13) . . ?
O7 C16 C13 124.6(14) . . ?
O8 C16 C13 113.1(12) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 C20 118.3(13) . . ?
C18 C19 H19 120.9 . . ?
C18 C23 H23 119.6 . . ?
C18 C23 C22 120.8(13) . . ?
C22 C23 H23 119.6 . . ?
C11 C12 C13 119.3(13) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C2 C7 H7 120.2 . . ?
C2 C7 C6 119.6(13) . . ?
C6 C7 H7 120.2 . . ?
C35 N34 C36 117.3(17) . . ?
C33 N34 C35 119.4(16) . . ?
C33 N34 C36 123.3(16) . . ?
C21 C22 C25 119.8(14) . . ?
C21 C22 C23 117.1(15) . . ?
C23 C22 C25 123.2(14) . . ?
C31 O13 Bi2 94.0(10) . 3_545 ?
O16 C32 C29 117(2) . . ?
O15 C32 C29 123(2) . . ?
O15 C32 O16 119(2) . . ?
O12 C24 O11 125.1(13) . . ?
O12 C24 C20 120.4(13) . . ?
O11 C24 C20 114.5(13) . . ?
C5 C4 C8 121.9(13) . . ?
C5 C4 C3 123.3(13) . . ?
C3 C4 C8 114.6(12) . . ?
C7 C2 C1 119.9(12) . . ?
C7 C2 C3 121.9(13) . . ?
C3 C2 C1 118.1(12) . . ?
O1 C1 C2 119.2(12) . . ?
O2 C1 O1 119.8(13) . . ?
O2 C1 C2 121.0(12) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(14) . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C9 119.3(14) . . ?
C5 C6 C9 122.6(14) . . ?
C5 C6 C7 118.1(13) . . ?
C32 O16 H16 133.4 . . ?
N34 C36 H36A 109.5 . . ?
N34 C36 H36B 109.5 . . ?
N34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O4 C8 Bi1 60.5(7) . 2_465 ?
O4 C8 C4 120.5(13) . . ?
O3 C8 Bi1 56.6(7) . 2_465 ?
O3 C8 O4 117.0(13) . . ?
O3 C8 C4 122.3(13) . . ?
C4 C8 Bi1 172.4(10) . 2_465 ?
C4 C3 C2 116.7(12) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
O18 C33 N34 128.5(18) . . ?
O18 C33 H33 115.8 . . ?
N34 C33 H33 115.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.916
_oxdiff_exptl_absorpt_empirical_full_min 0.740
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.561(19)
2 0.439(19)

