# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_2-H
_database_code_depnum_ccdc_archive 'CCDC 2223276'
loop_
_audit_author_name
_audit_author_address
'Kai Oberdorf'
;Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H50 Bi3 F9 N4 O17 S3'
_chemical_formula_sum            'C52 H50 Bi3 F9 N4 O17 S3'
_chemical_formula_weight         1897.08

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   13.745(4)
_cell_length_b                   17.557(5)
_cell_length_c                   25.813(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6229(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9141
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.98


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.023
_exptl_crystal_F_000             3616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    8.651
_shelx_estimated_absorpt_T_min   0.185
_shelx_estimated_absorpt_T_max   0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2850
_exptl_absorpt_correction_T_max  0.4286
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0130
0.00 0.00 1.00 0.0320
-1.00 1.00 1.00 0.1010
1.00 1.00 -1.00 0.0600
1.00 1.00 0.00 0.0660
-1.00 -1.00 0.00 0.1200
1.00 -1.00 1.00 0.0750
-1.00 1.00 -1.00 0.1040
0.00 -1.00 1.00 0.0180
0.00 1.00 -1.00 0.0260
0.00 -1.00 0.00 0.0110
0.00 1.00 0.00 0.0300

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            80096
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.958
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10980
_reflns_number_gt                10288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.The 
atomic displacement parameters of atoms S1, O1, O2, O3, C1, F1, F2, F3 in 
residue OTF, O1, C1, C2, C3, C4 of residue Et2O, N1, C1, C2 of residue MECN 
were restraint with RIGU keyword in ShelXL input ('enhanced rigid bond' 
restraint for all bonds in the connectivity list. Standard values of 0.004 for 
both parameters s1 and s2 were used). The displacement parameters of atoms S1, 
O1, O2, O3, C1, F1, F2, F3 in residue OTF, O1, C1, C2, C3, C4 of residue Et2O, 
N1, C1, C2 of residue MECN were restrained to the same value with similarity 
restraint SIMU. The 1-2 and 1-3 distances in OTF residues were restrained to 
the same values with SAME. The Uii displacement parameters of atoms O1 O2 O3 
C1 F1 F2 F3 in residue OTF, O1, C1, C2 C3 C4 of residue Et2O were restrained 
with ISOR keyword to approximate isotropic behavior.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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 4413 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         10980
_refine_ls_number_parameters     846
_refine_ls_number_restraints     978
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0541
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.072
_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 0.73314(2) 0.49288(2) 0.76216(2) 0.02349(8) Uani 1 1 d . . . . .
Bi2 Bi 0.60130(2) 0.24393(2) 0.70383(2) 0.02763(8) Uani 1 1 d . . . . .
Bi3 Bi 0.41399(2) 0.47719(2) 0.66293(2) 0.02440(8) Uani 1 1 d . . . . .
N1 N 0.6948(4) 0.5775(3) 0.6447(2) 0.0218(14) Uani 1 1 d . . . . .
N2 N 0.8174(5) 0.3139(3) 0.6606(2) 0.0229(14) Uani 1 1 d . . . . .
N3 N 0.5087(5) 0.3606(4) 0.5678(2) 0.0256(15) Uani 1 1 d . . . . .
C1 C 0.7913(6) 0.5960(4) 0.7266(3) 0.0234(17) Uani 1 1 d . . . . .
C2 C 0.8577(6) 0.6418(4) 0.7541(3) 0.0297(19) Uani 1 1 d . . . . .
H2 H 0.878306 0.626264 0.787621 0.036 Uiso 1 1 calc R U . . .
C3 C 0.8928(6) 0.7077(5) 0.7338(3) 0.0327(19) Uani 1 1 d . . . . .
H3 H 0.938139 0.737308 0.752958 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8633(6) 0.7314(5) 0.6861(3) 0.034(2) Uani 1 1 d . . . . .
H4 H 0.887603 0.777762 0.672180 0.041 Uiso 1 1 calc R U . . .
C5 C 0.7972(6) 0.6878(4) 0.6576(3) 0.0294(19) Uani 1 1 d . . . . .
H5 H 0.777501 0.704354 0.624206 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7602(6) 0.6204(4) 0.6777(3) 0.0252(18) Uani 1 1 d . . . . .
C7 C 0.7115(6) 0.5835(4) 0.5900(3) 0.0247(17) Uani 1 1 d . . . . .
C8 C 0.7957(6) 0.5503(4) 0.5698(3) 0.0275(18) Uani 1 1 d . . . . .
H8 H 0.837399 0.521209 0.591486 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8177(6) 0.5604(5) 0.5180(4) 0.038(2) Uani 1 1 d . . . . .
H9 H 0.875085 0.538326 0.503941 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7583(7) 0.6012(6) 0.4874(3) 0.046(3) Uani 1 1 d . . . . .
H10 H 0.774122 0.607745 0.451877 0.056 Uiso 1 1 calc R U . . .
C11 C 0.6748(9) 0.6338(6) 0.5067(4) 0.052(3) Uani 1 1 d . . . . .
H11 H 0.633641 0.662495 0.484528 0.062 Uiso 1 1 calc R U . . .
C12 C 0.6501(6) 0.6247(5) 0.5596(3) 0.037(2) Uani 1 1 d . . . . .
H12 H 0.592585 0.646673 0.573467 0.044 Uiso 1 1 calc R U . . .
C13 C 0.6211(5) 0.5330(4) 0.6618(3) 0.0222(16) Uani 1 1 d . . . . .
O1 O 0.6080(3) 0.5200(3) 0.71040(17) 0.0251(11) Uani 1 1 d . . . . .
O2 O 0.5641(3) 0.5042(3) 0.62829(18) 0.0243(11) Uani 1 1 d . . . . .
C14 C 0.7360(6) 0.1877(4) 0.6775(3) 0.0269(18) Uani 1 1 d . . . . .
C15 C 0.7453(6) 0.1084(4) 0.6786(3) 0.035(2) Uani 1 1 d . . . . .
H15 H 0.691726 0.078363 0.689733 0.042 Uiso 1 1 calc R U . . .
C16 C 0.8302(7) 0.0728(5) 0.6641(4) 0.039(2) Uani 1 1 d . . . . .
H16 H 0.833969 0.018797 0.663990 0.046 Uiso 1 1 calc R U . . .
C17 C 0.9101(8) 0.1158(5) 0.6495(3) 0.042(2) Uani 1 1 d . . . . .
H17 H 0.969002 0.091371 0.639835 0.050 Uiso 1 1 calc R U . . .
C18 C 0.9038(6) 0.1941(4) 0.6492(3) 0.0314(19) Uani 1 1 d . . . . .
H18 H 0.959009 0.223480 0.639645 0.038 Uiso 1 1 calc R U . . .
C19 C 0.8174(6) 0.2310(4) 0.6627(3) 0.0231(16) Uani 1 1 d . . . . .
C20 C 0.8781(5) 0.3480(4) 0.6210(3) 0.0227(17) Uani 1 1 d . . . . .
C21 C 0.8544(6) 0.3361(4) 0.5701(3) 0.0271(18) Uani 1 1 d . . . . .
H21 H 0.797746 0.308013 0.561281 0.032 Uiso 1 1 calc R U . . .
C22 C 0.9138(6) 0.3654(5) 0.5319(3) 0.0328(19) Uani 1 1 d . . . . .
H22 H 0.897807 0.357098 0.496495 0.039 Uiso 1 1 calc R U . . .
C23 C 0.9957(7) 0.4064(5) 0.5444(3) 0.039(2) Uani 1 1 d . . . . .
H23 H 1.035926 0.426714 0.517792 0.047 Uiso 1 1 calc R U . . .
C24 C 1.0189(6) 0.4178(5) 0.5954(3) 0.037(2) Uani 1 1 d . . . . .
H24 H 1.075418 0.446305 0.604057 0.045 Uiso 1 1 calc R U . . .
C25 C 0.9618(6) 0.3886(5) 0.6344(3) 0.0305(19) Uani 1 1 d . . . . .
H25 H 0.978876 0.395921 0.669683 0.037 Uiso 1 1 calc R U . . .
C26 C 0.7700(6) 0.3580(4) 0.6941(3) 0.0226(17) Uani 1 1 d . . . . .
O3 O 0.7081(4) 0.3330(3) 0.72628(19) 0.0254(12) Uani 1 1 d . . . . .
O4 O 0.7864(4) 0.4308(3) 0.69223(19) 0.0237(12) Uani 1 1 d . . . . .
C27 C 0.3686(5) 0.4506(4) 0.5824(3) 0.0255(18) Uani 1 1 d . . . . .
C28 C 0.2886(6) 0.4856(5) 0.5606(3) 0.0334(19) Uani 1 1 d . . . . .
H28 H 0.256090 0.524250 0.579619 0.040 Uiso 1 1 calc R U . . .
C29 C 0.2542(6) 0.4665(5) 0.5121(3) 0.035(2) Uani 1 1 d . . . . .
H29 H 0.197933 0.491008 0.498715 0.041 Uiso 1 1 calc R U . . .
C30 C 0.3010(6) 0.4121(5) 0.4833(4) 0.040(2) Uani 1 1 d . . . . .
H30 H 0.277458 0.398558 0.449900 0.048 Uiso 1 1 calc R U . . .
C31 C 0.3843(6) 0.3766(5) 0.5036(3) 0.035(2) Uani 1 1 d . . . . .
H31 H 0.416398 0.338289 0.484092 0.042 Uiso 1 1 calc R U . . .
C32 C 0.4204(6) 0.3969(4) 0.5521(3) 0.0275(18) Uani 1 1 d . . . . .
C33 C 0.5797(6) 0.3454(5) 0.5269(3) 0.0290(18) Uani 1 1 d . . . . .
C34 C 0.6005(6) 0.2733(5) 0.5119(3) 0.0336(19) Uani 1 1 d . . . . .
H34 H 0.571326 0.231349 0.529261 0.040 Uiso 1 1 calc R U . . .
C35 C 0.6640(6) 0.2608(5) 0.4715(3) 0.041(2) Uani 1 1 d . . . . .
H35 H 0.677681 0.210229 0.460618 0.049 Uiso 1 1 calc R U . . .
C36 C 0.7084(7) 0.3223(5) 0.4463(4) 0.043(2) Uani 1 1 d . . . . .
H36 H 0.754087 0.313658 0.419291 0.052 Uiso 1 1 calc R U . . .
C37 C 0.6849(6) 0.3958(5) 0.4612(3) 0.037(2) Uani 1 1 d . . . . .
H37 H 0.712464 0.438033 0.443531 0.045 Uiso 1 1 calc R U . . .
C38 C 0.6206(6) 0.4076(5) 0.5024(3) 0.033(2) Uani 1 1 d . . . . .
H38 H 0.605126 0.457791 0.513419 0.040 Uiso 1 1 calc R U . . .
C39 C 0.5321(6) 0.3410(4) 0.6173(3) 0.0261(18) Uani 1 1 d . . . . .
O5 O 0.4754(4) 0.3586(3) 0.6550(2) 0.0288(13) Uani 1 1 d . . . . .
O6 O 0.6076(4) 0.3007(3) 0.6248(2) 0.0290(13) Uani 1 1 d . . . . .
S1_1 S 0.95579(14) 0.40802(11) 0.80036(8) 0.0316(5) Uani 1 1 d D U . . .
O1_1 O 0.9066(4) 0.4781(2) 0.78720(19) 0.0373(13) Uani 1 1 d D U . . .
O2_1 O 1.0593(3) 0.4128(3) 0.7986(2) 0.0395(14) Uani 1 1 d D U . . .
O3_1 O 0.9142(4) 0.3418(3) 0.7760(2) 0.0460(16) Uani 1 1 d D U . . .
C1_1 C 0.9266(4) 0.3964(3) 0.8683(2) 0.0446(17) Uani 1 1 d D U . . .
F1_1 F 0.9571(4) 0.3300(3) 0.8858(2) 0.0622(16) Uani 1 1 d D U . . .
F2_1 F 0.8309(4) 0.3997(4) 0.8746(2) 0.077(2) Uani 1 1 d D U . . .
F3_1 F 0.9665(4) 0.4520(3) 0.8957(2) 0.0667(17) Uani 1 1 d D U . . .
S1_2 S 0.44192(17) 0.10993(13) 0.65447(9) 0.0427(6) Uani 1 1 d D U . . .
O1_2 O 0.5126(4) 0.1107(4) 0.6956(2) 0.0654(19) Uani 1 1 d D U . . .
O2_2 O 0.4484(6) 0.1742(3) 0.6208(3) 0.087(3) Uani 1 1 d D U . . .
O3_2 O 0.3456(3) 0.0909(3) 0.6714(2) 0.0439(15) Uani 1 1 d D U . . .
C1_2 C 0.4783(4) 0.0296(4) 0.6151(2) 0.0528(18) Uani 1 1 d D U . . .
F1_2 F 0.4188(5) 0.0239(4) 0.5752(2) 0.091(2) Uani 1 1 d D U . . .
F2_2 F 0.4742(5) -0.0337(3) 0.6424(3) 0.090(2) Uani 1 1 d D U . . .
F3_2 F 0.5673(4) 0.0371(4) 0.5971(2) 0.0768(19) Uani 1 1 d D U . . .
S1_3 S 0.41733(17) 0.68592(12) 0.66558(9) 0.0422(5) Uani 1 1 d D U . . .
O1_3 O 0.4108(5) 0.6172(3) 0.6353(2) 0.0495(15) Uani 1 1 d D U . . .
O2_3 O 0.5137(3) 0.7133(4) 0.6751(3) 0.066(2) Uani 1 1 d D U . . .
O3_3 O 0.3538(4) 0.6858(3) 0.71013(18) 0.0420(14) Uani 1 1 d D U . . .
C1_3 C 0.3629(4) 0.7571(3) 0.6237(2) 0.0565(18) Uani 1 1 d D U . . .
F1_3 F 0.3617(5) 0.8239(3) 0.6471(2) 0.0758(19) Uani 1 1 d D U . . .
F2_3 F 0.2724(4) 0.7388(3) 0.6116(2) 0.0716(17) Uani 1 1 d D U . . .
F3_3 F 0.4117(5) 0.7631(4) 0.5798(2) 0.095(2) Uani 1 1 d D U . . .
O1_4 O 0.6721(8) 0.8501(6) 0.4968(4) 0.099(2) Uani 1 1 d . U . . .
C1_4 C 0.5523(10) 0.8554(8) 0.4361(5) 0.083(3) Uani 1 1 d . U . . .
H1A_4 H 0.481923 0.858747 0.430442 0.125 Uiso 1 1 calc R U . . .
H1B_4 H 0.578106 0.810941 0.417667 0.125 Uiso 1 1 calc R U . . .
H1C_4 H 0.583702 0.901644 0.423016 0.125 Uiso 1 1 calc R U . . .
C2_4 C 0.5718(11) 0.8476(8) 0.4912(5) 0.088(3) Uani 1 1 d . U . . .
H2A_4 H 0.540971 0.889686 0.510751 0.105 Uiso 1 1 calc R U . . .
H2AB_4 H 0.545906 0.798649 0.504323 0.105 Uiso 1 1 calc R U . . .
C3_4 C 0.7073(12) 0.8459(10) 0.5499(6) 0.110(3) Uani 1 1 d . U . . .
H3A_4 H 0.682994 0.799227 0.567148 0.132 Uiso 1 1 calc R U . . .
H3AB_4 H 0.685635 0.890804 0.570011 0.132 Uiso 1 1 calc R U . . .
C4_4 C 0.8227(12) 0.8441(10) 0.5454(7) 0.125(5) Uani 1 1 d . U . . .
H4A_4 H 0.851530 0.861108 0.578128 0.188 Uiso 1 1 calc R U . . .
H4B_4 H 0.843524 0.878144 0.517373 0.188 Uiso 1 1 calc R U . . .
H4C_4 H 0.844250 0.792094 0.537815 0.188 Uiso 1 1 calc R U . . .
O1_5 O 0.8000(11) 0.1063(8) 0.2848(6) 0.042(2) Uani 0.572(9) 1 d . U P A 1
C1_5 C 0.7297(14) 0.2009(12) 0.3410(8) 0.044(4) Uani 0.572(9) 1 d . U P A 1
H1A_5 H 0.667981 0.219251 0.355293 0.065 Uiso 0.572(9) 1 calc R U P A 1
H1B_5 H 0.760473 0.241649 0.320855 0.065 Uiso 0.572(9) 1 calc R U P A 1
H1C_5 H 0.772964 0.185676 0.369332 0.065 Uiso 0.572(9) 1 calc R U P A 1
C2_5 C 0.7107(12) 0.1329(10) 0.3060(7) 0.044(2) Uani 0.572(9) 1 d . U P A 1
H2A_5 H 0.679459 0.091637 0.326210 0.053 Uiso 0.572(9) 1 calc R U P A 1
H2AB_5 H 0.665999 0.147784 0.277726 0.053 Uiso 0.572(9) 1 calc R U P A 1
C3_5 C 0.8410(14) 0.1501(10) 0.2445(6) 0.045(2) Uani 0.572(9) 1 d . U P A 1
H3A_5 H 0.911593 0.154132 0.251624 0.054 Uiso 0.572(9) 1 calc R U P A 1
H3AB_5 H 0.813925 0.202182 0.247652 0.054 Uiso 0.572(9) 1 calc R U P A 1
C4_5 C 0.8307(15) 0.1274(11) 0.1893(7) 0.054(3) Uani 0.572(9) 1 d . U P A 1
H4A_5 H 0.878369 0.155080 0.168266 0.081 Uiso 0.572(9) 1 calc R U P A 1
H4B_5 H 0.764875 0.139615 0.177250 0.081 Uiso 0.572(9) 1 calc R U P A 1
H4C_5 H 0.841946 0.072503 0.185953 0.081 Uiso 0.572(9) 1 calc R U P A 1
O1_15 O 0.8226(15) 0.1279(11) 0.2873(9) 0.044(2) Uani 0.428(9) 1 d . U P A 2
C1_15 C 0.694(2) 0.1909(17) 0.3343(11) 0.044(4) Uani 0.428(9) 1 d . U P A 2
H1A_15 H 0.665594 0.240621 0.342211 0.066 Uiso 0.428(9) 1 calc R U P A 2
H1B_15 H 0.707874 0.163638 0.366605 0.066 Uiso 0.428(9) 1 calc R U P A 2
H1C_15 H 0.648824 0.161145 0.313199 0.066 Uiso 0.428(9) 1 calc R U P A 2
C2_15 C 0.7863(16) 0.2019(13) 0.3052(9) 0.044(2) Uani 0.428(9) 1 d . U P A 2
H2A_15 H 0.774695 0.235699 0.275118 0.053 Uiso 0.428(9) 1 calc R U P A 2
H2AB_15 H 0.835308 0.226392 0.327850 0.053 Uiso 0.428(9) 1 calc R U P A 2
C3_15 C 0.7889(17) 0.1064(13) 0.2353(8) 0.045(2) Uani 0.428(9) 1 d . U P A 2
H3A_15 H 0.745146 0.144394 0.219235 0.054 Uiso 0.428(9) 1 calc R U P A 2
H3AB_15 H 0.760410 0.054694 0.233580 0.054 Uiso 0.428(9) 1 calc R U P A 2
C4_15 C 0.9002(19) 0.1108(14) 0.2146(9) 0.055(4) Uani 0.428(9) 1 d . U P A 2
H4A_15 H 0.905751 0.151532 0.188795 0.083 Uiso 0.428(9) 1 calc R U P A 2
H4B_15 H 0.918128 0.062095 0.198775 0.083 Uiso 0.428(9) 1 calc R U P A 2
H4C_15 H 0.943817 0.121563 0.243725 0.083 Uiso 0.428(9) 1 calc R U P A 2
N1_6 N 0.2309(6) 0.5343(6) 0.6756(3) 0.062(2) Uani 1 1 d . U . . .
C1_6 C 0.1774(8) 0.5796(8) 0.6893(4) 0.068(3) Uani 1 1 d . U . . .
C2_6 C 0.1093(10) 0.6392(9) 0.7063(5) 0.099(4) Uani 1 1 d . U . . .
H2A_6 H 0.049851 0.615512 0.719686 0.148 Uiso 1 1 calc R U . . .
H2B_6 H 0.092975 0.672109 0.676856 0.148 Uiso 1 1 calc R U . . .
H2C_6 H 0.139654 0.669782 0.733630 0.148 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 C1 2.181(8) . ?
Bi1 O1 2.229(5) . ?
Bi1 O4 2.232(5) . ?
Bi1 O1_1 2.484(5) . ?
Bi1 O3_2 2.659(5) 3_656 ?
Bi2 C14 2.206(8) . ?
Bi2 O3 2.222(5) . ?
Bi2 O6 2.273(5) . ?
Bi2 O3_3 2.521(5) 3_646 ?
Bi2 O1_2 2.647(7) . ?
Bi3 C27 2.219(7) . ?
Bi3 O5 2.256(5) . ?
Bi3 O2 2.298(5) . ?
Bi3 O1_5 2.535(15) 4_456 ?
Bi3 O1_3 2.560(5) . ?
Bi3 O1_15 2.57(2) 4_456 ?
Bi3 N1_6 2.729(8) . ?
N1 C13 1.354(9) . ?
N1 C7 1.435(9) . ?
N1 C6 1.450(10) . ?
N2 C26 1.332(10) . ?
N2 C20 1.448(10) . ?
N2 C19 1.457(9) . ?
N3 C39 1.360(10) . ?
N3 C32 1.429(10) . ?
N3 C33 1.462(10) . ?
C1 C6 1.398(11) . ?
C1 C2 1.409(11) . ?
C2 C3 1.359(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(11) . ?
C5 H5 0.9500 . ?
C7 C12 1.360(11) . ?
C7 C8 1.395(11) . ?
C8 C9 1.384(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.344(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(13) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O2 1.273(8) . ?
C13 O1 1.287(9) . ?
C14 C15 1.398(10) . ?
C14 C19 1.405(11) . ?
C15 C16 1.376(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(11) . ?
C17 H17 0.9500 . ?
C18 C19 1.397(11) . ?
C18 H18 0.9500 . ?
C20 C21 1.367(11) . ?
C20 C25 1.398(11) . ?
C21 C22 1.381(11) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.371(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(12) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 O3 1.267(9) . ?
C26 O4 1.299(9) . ?
C27 C28 1.379(11) . ?
C27 C32 1.418(11) . ?
C28 C29 1.379(11) . ?
C28 H28 0.9500 . ?
C29 C30 1.372(13) . ?
C29 H29 0.9500 . ?
C30 C31 1.405(12) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(11) . ?
C31 H31 0.9500 . ?
C33 C34 1.354(11) . ?
C33 C38 1.382(11) . ?
C34 C35 1.379(12) . ?
C34 H34 0.9500 . ?
C35 C36 1.400(13) . ?
C35 H35 0.9500 . ?
C36 C37 1.385(12) . ?
C36 H36 0.9500 . ?
C37 C38 1.399(11) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 O6 1.271(9) . ?
C39 O5 1.284(9) . ?
S1_1 O2_1 1.425(4) . ?
S1_1 O3_1 1.440(4) . ?
S1_1 O1_1 1.444(4) . ?
S1_1 C1_1 1.810(7) . ?
C1_1 F1_1 1.319(5) . ?
C1_1 F3_1 1.325(5) . ?
C1_1 F2_1 1.327(5) . ?
S1_2 O2_2 1.428(4) . ?
S1_2 O3_2 1.434(4) . ?
S1_2 O1_2 1.439(4) . ?
S1_2 C1_2 1.808(7) . ?
C1_2 F3_2 1.315(5) . ?
C1_2 F2_2 1.317(5) . ?
C1_2 F1_2 1.321(5) . ?
S1_3 O2_3 1.430(4) . ?
S1_3 O1_3 1.441(4) . ?
S1_3 O3_3 1.444(4) . ?
S1_3 C1_3 1.814(7) . ?
C1_3 F1_3 1.319(5) . ?
C1_3 F3_3 1.319(5) . ?
C1_3 F2_3 1.323(5) . ?
O1_4 C2_4 1.387(17) . ?
O1_4 C3_4 1.456(17) . ?
C1_4 C2_4 1.454(17) . ?
C1_4 H1A_4 0.9800 . ?
C1_4 H1B_4 0.9800 . ?
C1_4 H1C_4 0.9800 . ?
C2_4 H2A_4 0.9900 . ?
C2_4 H2AB_4 0.9900 . ?
C3_4 C4_4 1.59(2) . ?
C3_4 H3A_4 0.9900 . ?
C3_4 H3AB_4 0.9900 . ?
C4_4 H4A_4 0.9800 . ?
C4_4 H4B_4 0.9800 . ?
C4_4 H4C_4 0.9800 . ?
O1_5 C3_5 1.41(2) . ?
O1_5 C2_5 1.42(2) . ?
C1_5 C2_5 1.52(3) . ?
C1_5 H1A_5 0.9800 . ?
C1_5 H1B_5 0.9800 . ?
C1_5 H1C_5 0.9800 . ?
C2_5 H2A_5 0.9900 . ?
C2_5 H2AB_5 0.9900 . ?
C3_5 C4_5 1.49(2) . ?
C3_5 H3A_5 0.9900 . ?
C3_5 H3AB_5 0.9900 . ?
C4_5 H4A_5 0.9800 . ?
C4_5 H4B_5 0.9800 . ?
C4_5 H4C_5 0.9800 . ?
O1_15 C2_15 1.47(3) . ?
O1_15 C3_15 1.47(3) . ?
C1_15 C2_15 1.48(4) . ?
C1_15 H1A_15 0.9800 . ?
C1_15 H1B_15 0.9800 . ?
C1_15 H1C_15 0.9800 . ?
C2_15 H2A_15 0.9900 . ?
C2_15 H2AB_15 0.9900 . ?
C3_15 C4_15 1.62(3) . ?
C3_15 H3A_15 0.9900 . ?
C3_15 H3AB_15 0.9900 . ?
C4_15 H4A_15 0.9800 . ?
C4_15 H4B_15 0.9800 . ?
C4_15 H4C_15 0.9800 . ?
N1_6 C1_6 1.138(13) . ?
C1_6 C2_6 1.472(16) . ?
C2_6 H2A_6 0.9800 . ?
C2_6 H2B_6 0.9800 . ?
C2_6 H2C_6 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 O1 81.6(2) . . ?
C1 Bi1 O4 86.8(2) . . ?
O1 Bi1 O4 82.67(18) . . ?
C1 Bi1 O1_1 81.1(2) . . ?
O1 Bi1 O1_1 156.76(17) . . ?
O4 Bi1 O1_1 81.06(18) . . ?
C1 Bi1 O3_2 83.3(2) . 3_656 ?
O1 Bi1 O3_2 86.24(17) . 3_656 ?
O4 Bi1 O3_2 166.12(18) . 3_656 ?
O1_1 Bi1 O3_2 106.88(17) . 3_656 ?
C14 Bi2 O3 80.8(2) . . ?
C14 Bi2 O6 83.5(2) . . ?
O3 Bi2 O6 84.30(19) . . ?
C14 Bi2 O3_3 83.4(2) . 3_646 ?
O3 Bi2 O3_3 83.85(19) . 3_646 ?
O6 Bi2 O3_3 163.58(18) . 3_646 ?
C14 Bi2 O1_2 88.1(2) . . ?
O3 Bi2 O1_2 161.34(18) . . ?
O6 Bi2 O1_2 109.45(18) . . ?
O3_3 Bi2 O1_2 79.97(18) 3_646 . ?
C27 Bi3 O5 80.0(2) . . ?
C27 Bi3 O2 86.1(2) . . ?
O5 Bi3 O2 79.57(19) . . ?
C27 Bi3 O1_5 101.7(4) . 4_456 ?
O5 Bi3 O1_5 75.3(3) . 4_456 ?
O2 Bi3 O1_5 151.8(3) . 4_456 ?
C27 Bi3 O1_3 86.3(2) . . ?
O5 Bi3 O1_3 150.12(19) . . ?
O2 Bi3 O1_3 73.1(2) . . ?
O1_5 Bi3 O1_3 133.9(3) 4_456 . ?
C27 Bi3 O1_15 100.3(6) . 4_456 ?
O5 Bi3 O1_15 64.3(4) . 4_456 ?
O2 Bi3 O1_15 141.2(4) . 4_456 ?
O1_5 Bi3 O1_15 11.1(5) 4_456 4_456 ?
O1_3 Bi3 O1_15 144.9(4) . 4_456 ?
C27 Bi3 N1_6 86.0(3) . . ?
O5 Bi3 N1_6 134.0(3) . . ?
O2 Bi3 N1_6 143.0(2) . . ?
O1_5 Bi3 N1_6 65.1(4) 4_456 . ?
O1_3 Bi3 N1_6 70.4(3) . . ?
O1_15 Bi3 N1_6 75.7(5) 4_456 . ?
C13 N1 C7 119.0(6) . . ?
C13 N1 C6 124.8(6) . . ?
C7 N1 C6 116.2(6) . . ?
C26 N2 C20 120.0(6) . . ?
C26 N2 C19 123.8(7) . . ?
C20 N2 C19 116.1(6) . . ?
C39 N3 C32 125.4(7) . . ?
C39 N3 C33 118.3(7) . . ?
C32 N3 C33 116.3(6) . . ?
C6 C1 C2 118.5(7) . . ?
C6 C1 Bi1 121.5(6) . . ?
C2 C1 Bi1 119.9(6) . . ?
C3 C2 C1 121.4(8) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.2(8) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.1(8) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.6(8) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.1(7) . . ?
C5 C6 N1 116.7(7) . . ?
C1 C6 N1 124.1(7) . . ?
C12 C7 C8 121.4(8) . . ?
C12 C7 N1 120.4(7) . . ?
C8 C7 N1 118.0(7) . . ?
C9 C8 C7 119.3(8) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 120.2(8) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.1(9) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 120.2(9) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 117.8(9) . . ?
C7 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
O2 C13 O1 120.4(6) . . ?
O2 C13 N1 117.9(7) . . ?
O1 C13 N1 121.7(7) . . ?
C13 O1 Bi1 120.9(4) . . ?
C13 O2 Bi3 111.7(4) . . ?
C15 C14 C19 118.2(7) . . ?
C15 C14 Bi2 121.0(6) . . ?
C19 C14 Bi2 120.6(5) . . ?
C16 C15 C14 121.6(8) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 120.0(8) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.7(9) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.9(9) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C14 119.6(7) . . ?
C18 C19 N2 117.0(7) . . ?
C14 C19 N2 123.5(6) . . ?
C21 C20 C25 120.7(7) . . ?
C21 C20 N2 118.5(7) . . ?
C25 C20 N2 120.7(7) . . ?
C20 C21 C22 119.3(8) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 120.7(8) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 119.5(8) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 121.0(8) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C20 118.7(8) . . ?
C24 C25 H25 120.7 . . ?
C20 C25 H25 120.7 . . ?
O3 C26 O4 118.9(7) . . ?
O3 C26 N2 123.5(7) . . ?
O4 C26 N2 117.6(7) . . ?
C26 O3 Bi2 121.1(5) . . ?
C26 O4 Bi1 113.1(4) . . ?
C28 C27 C32 118.0(7) . . ?
C28 C27 Bi3 120.9(6) . . ?
C32 C27 Bi3 121.0(5) . . ?
C29 C28 C27 122.5(8) . . ?
C29 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C30 C29 C28 120.0(8) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 119.2(8) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C32 C31 C30 120.9(9) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C27 119.2(8) . . ?
C31 C32 N3 116.3(7) . . ?
C27 C32 N3 124.5(7) . . ?
C34 C33 C38 121.5(8) . . ?
C34 C33 N3 121.3(8) . . ?
C38 C33 N3 117.2(7) . . ?
C33 C34 C35 119.9(9) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 120.4(8) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 119.2(8) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C36 C37 C38 119.8(9) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C33 C38 C37 119.2(8) . . ?
C33 C38 H38 120.4 . . ?
C37 C38 H38 120.4 . . ?
O6 C39 O5 120.9(7) . . ?
O6 C39 N3 118.5(7) . . ?
O5 C39 N3 120.4(7) . . ?
C39 O5 Bi3 121.2(5) . . ?
C39 O6 Bi2 110.5(5) . . ?
O2_1 S1_1 O3_1 115.5(3) . . ?
O2_1 S1_1 O1_1 114.1(3) . . ?
O3_1 S1_1 O1_1 113.5(3) . . ?
O2_1 S1_1 C1_1 105.0(3) . . ?
O3_1 S1_1 C1_1 104.1(3) . . ?
O1_1 S1_1 C1_1 102.7(3) . . ?
S1_1 O1_1 Bi1 126.8(3) . . ?
F1_1 C1_1 F3_1 109.7(5) . . ?
F1_1 C1_1 F2_1 108.2(5) . . ?
F3_1 C1_1 F2_1 108.2(5) . . ?
F1_1 C1_1 S1_1 111.2(4) . . ?
F3_1 C1_1 S1_1 110.1(4) . . ?
F2_1 C1_1 S1_1 109.5(4) . . ?
O2_2 S1_2 O3_2 115.3(4) . . ?
O2_2 S1_2 O1_2 113.6(4) . . ?
O3_2 S1_2 O1_2 113.6(4) . . ?
O2_2 S1_2 C1_2 104.9(3) . . ?
O3_2 S1_2 C1_2 104.2(3) . . ?
O1_2 S1_2 C1_2 103.6(3) . . ?
S1_2 O1_2 Bi2 112.2(4) . . ?
S1_2 O3_2 Bi1 136.3(4) . 3_646 ?
F3_2 C1_2 F2_2 108.2(6) . . ?
F3_2 C1_2 F1_2 107.9(5) . . ?
F2_2 C1_2 F1_2 109.0(6) . . ?
F3_2 C1_2 S1_2 112.2(4) . . ?
F2_2 C1_2 S1_2 110.3(5) . . ?
F1_2 C1_2 S1_2 109.1(4) . . ?
O2_3 S1_3 O1_3 115.6(4) . . ?
O2_3 S1_3 O3_3 115.1(4) . . ?
O1_3 S1_3 O3_3 113.2(4) . . ?
O2_3 S1_3 C1_3 104.7(3) . . ?
O1_3 S1_3 C1_3 103.1(3) . . ?
O3_3 S1_3 C1_3 103.1(3) . . ?
S1_3 O1_3 Bi3 130.7(3) . . ?
S1_3 O3_3 Bi2 123.6(3) . 3_656 ?
F1_3 C1_3 F3_3 109.2(6) . . ?
F1_3 C1_3 F2_3 108.1(5) . . ?
F3_3 C1_3 F2_3 107.2(6) . . ?
F1_3 C1_3 S1_3 110.1(4) . . ?
F3_3 C1_3 S1_3 110.9(5) . . ?
F2_3 C1_3 S1_3 111.1(4) . . ?
C2_4 O1_4 C3_4 115.2(13) . . ?
C2_4 C1_4 H1A_4 109.5 . . ?
C2_4 C1_4 H1B_4 109.5 . . ?
H1A_4 C1_4 H1B_4 109.5 . . ?
C2_4 C1_4 H1C_4 109.5 . . ?
H1A_4 C1_4 H1C_4 109.5 . . ?
H1B_4 C1_4 H1C_4 109.5 . . ?
O1_4 C2_4 C1_4 106.4(13) . . ?
O1_4 C2_4 H2A_4 110.5 . . ?
C1_4 C2_4 H2A_4 110.5 . . ?
O1_4 C2_4 H2AB_4 110.5 . . ?
C1_4 C2_4 H2AB_4 110.5 . . ?
H2A_4 C2_4 H2AB_4 108.6 . . ?
O1_4 C3_4 C4_4 105.2(14) . . ?
O1_4 C3_4 H3A_4 110.7 . . ?
C4_4 C3_4 H3A_4 110.7 . . ?
O1_4 C3_4 H3AB_4 110.7 . . ?
C4_4 C3_4 H3AB_4 110.7 . . ?
H3A_4 C3_4 H3AB_4 108.8 . . ?
C3_4 C4_4 H4A_4 109.5 . . ?
C3_4 C4_4 H4B_4 109.5 . . ?
H4A_4 C4_4 H4B_4 109.5 . . ?
C3_4 C4_4 H4C_4 109.5 . . ?
H4A_4 C4_4 H4C_4 109.5 . . ?
H4B_4 C4_4 H4C_4 109.5 . . ?
C3_5 O1_5 C2_5 116.7(14) . . ?
C3_5 O1_5 Bi3 117.5(11) . 4_556 ?
C2_5 O1_5 Bi3 121.1(11) . 4_556 ?
C2_5 C1_5 H1A_5 109.5 . . ?
C2_5 C1_5 H1B_5 109.5 . . ?
H1A_5 C1_5 H1B_5 109.5 . . ?
C2_5 C1_5 H1C_5 109.5 . . ?
H1A_5 C1_5 H1C_5 109.5 . . ?
H1B_5 C1_5 H1C_5 109.5 . . ?
O1_5 C2_5 C1_5 109.8(14) . . ?
O1_5 C2_5 H2A_5 109.7 . . ?
C1_5 C2_5 H2A_5 109.7 . . ?
O1_5 C2_5 H2AB_5 109.7 . . ?
C1_5 C2_5 H2AB_5 109.7 . . ?
H2A_5 C2_5 H2AB_5 108.2 . . ?
O1_5 C3_5 C4_5 121.4(16) . . ?
O1_5 C3_5 H3A_5 107.0 . . ?
C4_5 C3_5 H3A_5 107.0 . . ?
O1_5 C3_5 H3AB_5 107.0 . . ?
C4_5 C3_5 H3AB_5 107.0 . . ?
H3A_5 C3_5 H3AB_5 106.7 . . ?
C3_5 C4_5 H4A_5 109.5 . . ?
C3_5 C4_5 H4B_5 109.5 . . ?
H4A_5 C4_5 H4B_5 109.5 . . ?
C3_5 C4_5 H4C_5 109.5 . . ?
H4A_5 C4_5 H4C_5 109.5 . . ?
H4B_5 C4_5 H4C_5 109.5 . . ?
C2_15 O1_15 C3_15 114.1(19) . . ?
C2_15 C1_15 H1A_15 109.5 . . ?
C2_15 C1_15 H1B_15 109.5 . . ?
H1A_15 C1_15 H1B_15 109.5 . . ?
C2_15 C1_15 H1C_15 109.5 . . ?
H1A_15 C1_15 H1C_15 109.5 . . ?
H1B_15 C1_15 H1C_15 109.5 . . ?
O1_15 C2_15 C1_15 109(2) . . ?
O1_15 C2_15 H2A_15 109.8 . . ?
C1_15 C2_15 H2A_15 109.8 . . ?
O1_15 C2_15 H2AB_15 109.8 . . ?
C1_15 C2_15 H2AB_15 109.8 . . ?
H2A_15 C2_15 H2AB_15 108.2 . . ?
O1_15 C3_15 C4_15 89.6(17) . . ?
O1_15 C3_15 H3A_15 113.7 . . ?
C4_15 C3_15 H3A_15 113.7 . . ?
O1_15 C3_15 H3AB_15 113.7 . . ?
C4_15 C3_15 H3AB_15 113.7 . . ?
H3A_15 C3_15 H3AB_15 111.0 . . ?
C3_15 C4_15 H4A_15 109.5 . . ?
C3_15 C4_15 H4B_15 109.5 . . ?
H4A_15 C4_15 H4B_15 109.5 . . ?
C3_15 C4_15 H4C_15 109.5 . . ?
H4A_15 C4_15 H4C_15 109.5 . . ?
H4B_15 C4_15 H4C_15 109.5 . . ?
C1_6 N1_6 Bi3 152.7(9) . . ?
N1_6 C1_6 C2_6 178.9(16) . . ?
C1_6 C2_6 H2A_6 109.5 . . ?
C1_6 C2_6 H2B_6 109.5 . . ?
H2A_6 C2_6 H2B_6 109.5 . . ?
C1_6 C2_6 H2C_6 109.5 . . ?
H2A_6 C2_6 H2C_6 109.5 . . ?
H2B_6 C2_6 H2C_6 109.5 . . ?

_refine_diff_density_max         1.116
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_3-Me
_database_code_depnum_ccdc_archive 'CCDC 2223277'
loop_
_audit_author_name
_audit_author_address
'Kai Oberdorf'
;Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 Bi F3 N O6 S3'
_chemical_formula_sum            'C22 H27 Bi F3 N O6 S3'
_chemical_formula_weight         763.60

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'
F F 0.0171 0.0103 '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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

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

_cell_length_a                   17.7035(14)
_cell_length_b                   24.613(2)
_cell_length_c                   14.9608(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6519.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9813
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.49


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             2976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.155
_exptl_absorpt_coefficient_mu    5.649
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1808
_exptl_absorpt_correction_T_max  0.2602
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            114474
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.593
_diffrn_reflns_theta_max         26.507
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6766
_reflns_number_gt                5720
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.The displacement parameters of atoms XXX 
and XXX of the residue YYY were constrained to the same value with EADP keyword.
The atomic displacement parameters of atoms XXX were restraint with RIGU 
keyword in ShelXL input ('enhanced rigid bond' restraint for all bonds in the 
connectivity list. Standard values of 0.004 for both parameters s1 and s2 were used).
The displacement parameters of atoms XXX and XXX of the residue YYY were 
restrained to the same value with similarity restraint SIMU.
The distances between atoms XXX and YYY were restrained during refinement to 
the same value.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+9.2898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6766
_refine_ls_number_parameters     483
_refine_ls_number_restraints     677
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0558
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.002

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_1 Bi 0.78991(2) 0.27478(2) 0.45260(2) 0.02073(4) Uani 1 1 d D . . . .
N1_1 N 0.71286(12) 0.34463(9) 0.24382(17) 0.0194(5) Uani 1 1 d . . . . .
C1_1 C 0.73508(16) 0.30698(12) 0.1855(2) 0.0205(6) Uani 1 1 d . . . . .
S1_1 S 0.82988(4) 0.29840(3) 0.16605(5) 0.02419(16) Uani 1 1 d . . . . .
S2_1 S 0.67159(4) 0.26589(3) 0.13076(5) 0.02031(15) Uani 1 1 d . . . . .
C2_2 C 0.63529(16) 0.36328(11) 0.2520(2) 0.0216(6) Uani 1 1 d . . . . .
C3_2 C 0.59594(18) 0.38091(13) 0.1770(2) 0.0287(7) Uani 1 1 d . . . . .
H3_2 H 0.618278 0.378603 0.119431 0.034 Uiso 1 1 calc R U . . .
C4_2 C 0.52358(18) 0.40196(13) 0.1872(3) 0.0350(8) Uani 1 1 d . . . . .
H4_2 H 0.496664 0.413834 0.135843 0.042 Uiso 1 1 calc R U . . .
C5_2 C 0.48983(17) 0.40600(13) 0.2704(3) 0.0333(8) Uani 1 1 d . . . . .
C6_2 C 0.53026(18) 0.38781(13) 0.3447(2) 0.0318(8) Uani 1 1 d . . . . .
H6_2 H 0.507725 0.389804 0.402231 0.038 Uiso 1 1 calc R U . . .
C7_2 C 0.60267(17) 0.36685(12) 0.3363(2) 0.0266(7) Uani 1 1 d . . . . .
H7_2 H 0.629676 0.355069 0.387598 0.032 Uiso 1 1 calc R U . . .
C8_2 C 0.41221(19) 0.43047(15) 0.2824(3) 0.0480(11) Uani 1 1 d . . . . .
H8A_2 H 0.380196 0.405176 0.315919 0.072 Uiso 1 1 calc R U . . .
H8B_2 H 0.389651 0.437376 0.223666 0.072 Uiso 1 1 calc R U . . .
H8C_2 H 0.416432 0.464741 0.315378 0.072 Uiso 1 1 calc R U . . .
C9_3 C 0.76868(15) 0.37491(12) 0.2949(2) 0.0215(6) Uani 1 1 d . . . . .
C10_3 C 0.78537(16) 0.42680(12) 0.2636(2) 0.0266(7) Uani 1 1 d . . . . .
H10_3 H 0.760972 0.440443 0.211701 0.032 Uiso 1 1 calc R U . . .
C11_3 C 0.83783(17) 0.45849(13) 0.3087(2) 0.0299(7) Uani 1 1 d . . . . .
H11_3 H 0.849339 0.493824 0.287049 0.036 Uiso 1 1 calc R U . . .
C12_3 C 0.87344(17) 0.43949(12) 0.3842(2) 0.0264(7) Uani 1 1 d . . . . .
C13_3 C 0.85514(17) 0.38771(13) 0.4146(2) 0.0261(7) Uani 1 1 d . . . . .
H13_3 H 0.878829 0.374833 0.467538 0.031 Uiso 1 1 calc R U . . .
C14_3 C 0.80359(15) 0.35369(12) 0.3712(2) 0.0219(6) Uani 1 1 d . . . . .
C15_3 C 0.93060(19) 0.47327(14) 0.4339(3) 0.0367(8) Uani 1 1 d . . . . .
H15A_3 H 0.928427 0.464523 0.497761 0.055 Uiso 1 1 calc R U . . .
H15B_3 H 0.919279 0.511895 0.425297 0.055 Uiso 1 1 calc R U . . .
H15C_3 H 0.981286 0.465390 0.410998 0.055 Uiso 1 1 calc R U . . .
C1_4 C 0.9856(12) 0.2838(6) 0.3588(13) 0.039(2) Uani 0.596(9) 1 d . U P A 1
H1A_4 H 1.025294 0.311158 0.366719 0.058 Uiso 0.596(9) 1 calc R U P A 1
H1B_4 H 0.950354 0.295978 0.312362 0.058 Uiso 0.596(9) 1 calc R U P A 1
H1C_4 H 1.008421 0.249250 0.340836 0.058 Uiso 0.596(9) 1 calc R U P A 1
O2_4 O 0.9460(15) 0.2768(8) 0.4406(14) 0.0304(16) Uani 0.596(9) 1 d . U P A 1
C3_4 C 0.9963(8) 0.2581(6) 0.5051(7) 0.0308(13) Uani 0.596(9) 1 d . U P A 1
H3A_4 H 1.037398 0.284864 0.513649 0.037 Uiso 0.596(9) 1 calc R U P A 1
H3B_4 H 1.019033 0.223349 0.485470 0.037 Uiso 0.596(9) 1 calc R U P A 1
C4_4 C 0.9544(7) 0.2499(7) 0.5915(9) 0.0311(13) Uani 0.596(9) 1 d . U P A 1
H4A_4 H 0.990203 0.239017 0.639069 0.037 Uiso 0.596(9) 1 calc R U P A 1
H4B_4 H 0.930062 0.284409 0.609843 0.037 Uiso 0.596(9) 1 calc R U P A 1
O5_4 O 0.8982(10) 0.2087(10) 0.5802(16) 0.0298(12) Uani 0.596(9) 1 d . U P A 1
C6_4 C 0.8560(5) 0.1986(5) 0.6554(9) 0.0315(13) Uani 0.596(9) 1 d . U P A 1
H6A_4 H 0.832250 0.232689 0.676313 0.038 Uiso 0.596(9) 1 calc R U P A 1
H6B_4 H 0.889263 0.184877 0.703605 0.038 Uiso 0.596(9) 1 calc R U P A 1
C7_4 C 0.7957(7) 0.1571(5) 0.6354(6) 0.0365(13) Uani 0.596(9) 1 d . U P A 1
H7A_4 H 0.766323 0.151099 0.690845 0.044 Uiso 0.596(9) 1 calc R U P A 1
H7B_4 H 0.821037 0.122401 0.620690 0.044 Uiso 0.596(9) 1 calc R U P A 1
O8_4 O 0.7390(5) 0.1699(3) 0.5594(5) 0.0390(13) Uani 0.596(9) 1 d . U P A 1
C9_4 C 0.6722(4) 0.1881(4) 0.5997(5) 0.055(2) Uani 0.596(9) 1 d . U P A 1
H9A_4 H 0.649876 0.158594 0.634811 0.082 Uiso 0.596(9) 1 calc R U P A 1
H9B_4 H 0.636468 0.199692 0.553455 0.082 Uiso 0.596(9) 1 calc R U P A 1
H9C_4 H 0.683530 0.218881 0.639153 0.082 Uiso 0.596(9) 1 calc R U P A 1
C1_14 C 0.9838(16) 0.2968(8) 0.3687(18) 0.031(3) Uani 0.404(9) 1 d . U P A 2
H1A_14 H 1.020905 0.325062 0.382750 0.047 Uiso 0.404(9) 1 calc R U P A 2
H1B_14 H 0.947646 0.310657 0.324737 0.047 Uiso 0.404(9) 1 calc R U P A 2
H1C_14 H 1.009844 0.264965 0.344078 0.047 Uiso 0.404(9) 1 calc R U P A 2
O2_14 O 0.944(2) 0.2813(13) 0.450(2) 0.0296(17) Uani 0.404(9) 1 d . U P A 2
C3_14 C 0.9906(13) 0.2591(10) 0.5225(11) 0.0303(14) Uani 0.404(9) 1 d . U P A 2
H3A_14 H 1.030970 0.285255 0.538001 0.036 Uiso 0.404(9) 1 calc R U P A 2
H3B_14 H 1.014759 0.224868 0.502633 0.036 Uiso 0.404(9) 1 calc R U P A 2
C4_14 C 0.9429(10) 0.2484(10) 0.6023(13) 0.0306(14) Uani 0.404(9) 1 d . U P A 2
H4A_14 H 0.974159 0.235060 0.652500 0.037 Uiso 0.404(9) 1 calc R U P A 2
H4B_14 H 0.916748 0.282057 0.621378 0.037 Uiso 0.404(9) 1 calc R U P A 2
O5_14 O 0.8907(15) 0.2092(15) 0.577(2) 0.0300(13) Uani 0.404(9) 1 d . U P A 2
C6_14 C 0.8409(8) 0.1923(7) 0.6520(13) 0.0319(14) Uani 0.404(9) 1 d . U P A 2
H6A_14 H 0.871535 0.177927 0.702006 0.038 Uiso 0.404(9) 1 calc R U P A 2
H6B_14 H 0.811225 0.223673 0.673942 0.038 Uiso 0.404(9) 1 calc R U P A 2
C7_14 C 0.7899(10) 0.1496(7) 0.6172(10) 0.0360(14) Uani 0.404(9) 1 d . U P A 2
H7A_14 H 0.814544 0.125694 0.572720 0.043 Uiso 0.404(9) 1 calc R U P A 2
H7B_14 H 0.766345 0.127660 0.665122 0.043 Uiso 0.404(9) 1 calc R U P A 2
O8_14 O 0.7417(8) 0.1852(5) 0.5799(8) 0.0397(16) Uani 0.404(9) 1 d . U P A 2
C9_14 C 0.6757(6) 0.1487(6) 0.5686(8) 0.052(2) Uani 0.404(9) 1 d . U P A 2
H9A_14 H 0.692587 0.113808 0.544326 0.078 Uiso 0.404(9) 1 calc R U P A 2
H9B_14 H 0.639521 0.165411 0.527241 0.078 Uiso 0.404(9) 1 calc R U P A 2
H9C_14 H 0.651365 0.142906 0.626614 0.078 Uiso 0.404(9) 1 calc R U P A 2
S3_5 S 0.7002(9) 0.3475(7) 0.6196(9) 0.0272(8) Uani 0.610(17) 1 d . U P A 1
O4_5 O 0.7842(8) 0.3432(6) 0.6198(9) 0.034(2) Uani 0.610(17) 1 d . U P A 1
O5_5 O 0.6718(5) 0.3228(4) 0.5330(10) 0.0285(13) Uani 0.610(17) 1 d D U P A 1
O6_5 O 0.6610(7) 0.3306(5) 0.6933(11) 0.0351(19) Uani 0.610(17) 1 d . U P A 1
C22_5 C 0.6923(4) 0.4214(4) 0.6138(5) 0.0366(12) Uani 0.610(17) 1 d D U P A 1
F1_5 F 0.7340(5) 0.4412(3) 0.5475(6) 0.0542(17) Uani 0.610(17) 1 d D U P A 1
F2_5 F 0.6210(4) 0.4366(4) 0.6007(5) 0.0496(16) Uani 0.610(17) 1 d D U P A 1
F3_5 F 0.7160(4) 0.4434(3) 0.6901(6) 0.0480(12) Uani 0.610(17) 1 d D U P A 1
S3_15 S 0.7031(15) 0.3464(11) 0.6135(16) 0.0304(11) Uani 0.390(17) 1 d . U P A
2
O4_15 O 0.7783(12) 0.3364(9) 0.6385(13) 0.026(2) Uani 0.390(17) 1 d . U P A 2
O5_15 O 0.6776(9) 0.3309(6) 0.5305(17) 0.0288(15) Uani 0.390(17) 1 d D U P A 2
O6_15 O 0.6473(11) 0.3399(8) 0.6919(18) 0.031(2) Uani 0.390(17) 1 d . U P A 2
C22_15 C 0.6836(8) 0.4179(7) 0.5920(10) 0.0368(13) Uani 0.390(17) 1 d . U P A 2
F1_15 F 0.7153(6) 0.4366(5) 0.5188(9) 0.0443(19) Uani 0.390(17) 1 d . U P A 2
F2_15 F 0.6088(7) 0.4250(6) 0.5833(9) 0.047(2) Uani 0.390(17) 1 d . U P A 2
F3_15 F 0.7082(7) 0.4492(5) 0.6617(9) 0.0480(12) Uani 0.390(17) 1 d . U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1_1 C14_3 2.305(3) . ?
Bi1_1 S1_1 2.6260(8) 4 ?
Bi1_1 S2_1 2.6354(7) 4 ?
Bi1_1 O5_5 2.685(3) . ?
Bi1_1 O5_15 2.687(4) . ?
Bi1_1 O2_14 2.73(4) . ?
N1_1 C1_1 1.332(4) . ?
N1_1 C2_2 1.453(3) . ?
N1_1 C9_3 1.454(4) . ?
C1_1 S1_1 1.716(3) . ?
C1_1 S2_1 1.720(3) . ?
C2_2 C7_2 1.389(4) . ?
C2_2 C3_2 1.390(4) . ?
C3_2 C4_2 1.390(4) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.385(5) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.396(5) . ?
C5_2 C8_2 1.511(4) . ?
C6_2 C7_2 1.388(4) . ?
C6_2 H6_2 0.9500 . ?
C7_2 H7_2 0.9500 . ?
C8_2 H8A_2 0.9800 . ?
C8_2 H8B_2 0.9800 . ?
C8_2 H8C_2 0.9800 . ?
C9_3 C10_3 1.392(4) . ?
C9_3 C14_3 1.399(4) . ?
C10_3 C11_3 1.388(4) . ?
C10_3 H10_3 0.9500 . ?
C11_3 C12_3 1.376(5) . ?
C11_3 H11_3 0.9500 . ?
C12_3 C13_3 1.391(4) . ?
C12_3 C15_3 1.506(4) . ?
C13_3 C14_3 1.399(4) . ?
C13_3 H13_3 0.9500 . ?
C15_3 H15A_3 0.9800 . ?
C15_3 H15B_3 0.9800 . ?
C15_3 H15C_3 0.9800 . ?
C1_4 O2_4 1.42(2) . ?
C1_4 H1A_4 0.9800 . ?
C1_4 H1B_4 0.9800 . ?
C1_4 H1C_4 0.9800 . ?
O2_4 C3_4 1.39(2) . ?
C3_4 C4_4 1.504(12) . ?
C3_4 H3A_4 0.9900 . ?
C3_4 H3B_4 0.9900 . ?
C4_4 O5_4 1.43(2) . ?
C4_4 H4A_4 0.9900 . ?
C4_4 H4B_4 0.9900 . ?
O5_4 C6_4 1.37(2) . ?
C6_4 C7_4 1.508(11) . ?
C6_4 H6A_4 0.9900 . ?
C6_4 H6B_4 0.9900 . ?
C7_4 O8_4 1.548(14) . ?
C7_4 H7A_4 0.9900 . ?
C7_4 H7B_4 0.9900 . ?
O8_4 C9_4 1.402(12) . ?
C9_4 H9A_4 0.9800 . ?
C9_4 H9B_4 0.9800 . ?
C9_4 H9C_4 0.9800 . ?
C1_14 O2_14 1.45(3) . ?
C1_14 H1A_14 0.9800 . ?
C1_14 H1B_14 0.9800 . ?
C1_14 H1C_14 0.9800 . ?
O2_14 C3_14 1.47(3) . ?
C3_14 C4_14 1.486(17) . ?
C3_14 H3A_14 0.9900 . ?
C3_14 H3B_14 0.9900 . ?
C4_14 O5_14 1.39(3) . ?
C4_14 H4A_14 0.9900 . ?
C4_14 H4B_14 0.9900 . ?
O5_14 C6_14 1.49(3) . ?
C6_14 C7_14 1.480(17) . ?
C6_14 H6A_14 0.9900 . ?
C6_14 H6B_14 0.9900 . ?
C7_14 O8_14 1.34(2) . ?
C7_14 H7A_14 0.9900 . ?
C7_14 H7B_14 0.9900 . ?
O8_14 C9_14 1.483(18) . ?
C9_14 H9A_14 0.9800 . ?
C9_14 H9B_14 0.9800 . ?
C9_14 H9C_14 0.9800 . ?
S3_5 O6_5 1.37(2) . ?
S3_5 O4_5 1.49(2) . ?
S3_5 O5_5 1.52(2) . ?
S3_5 C22_5 1.826(19) . ?
C22_5 F1_5 1.329(6) . ?
C22_5 F2_5 1.331(6) . ?
C22_5 F3_5 1.331(6) . ?
S3_15 O5_15 1.38(3) . ?
S3_15 O4_15 1.40(4) . ?
S3_15 O6_15 1.54(3) . ?
S3_15 C22_15 1.82(3) . ?
C22_15 F1_15 1.314(15) . ?
C22_15 F2_15 1.343(14) . ?
C22_15 F3_15 1.367(15) . ?

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
C14_3 Bi1_1 S1_1 101.10(8) . 4 ?
C14_3 Bi1_1 S2_1 98.83(7) . 4 ?
S1_1 Bi1_1 S2_1 68.52(2) 4 4 ?
C14_3 Bi1_1 O5_5 87.0(3) . . ?
S1_1 Bi1_1 O5_5 144.5(3) 4 . ?
S2_1 Bi1_1 O5_5 76.1(3) 4 . ?
C14_3 Bi1_1 O5_15 82.7(4) . . ?
S1_1 Bi1_1 O5_15 147.7(5) 4 . ?
S2_1 Bi1_1 O5_15 79.2(5) 4 . ?
C14_3 Bi1_1 O2_14 80.6(7) . . ?
S1_1 Bi1_1 O2_14 76.1(6) 4 . ?
S2_1 Bi1_1 O2_14 143.9(6) 4 . ?
O5_15 Bi1_1 O2_14 135.7(8) . . ?
C1_1 N1_1 C2_2 123.7(2) . . ?
C1_1 N1_1 C9_3 120.0(2) . . ?
C2_2 N1_1 C9_3 115.8(2) . . ?
N1_1 C1_1 S1_1 119.1(2) . . ?
N1_1 C1_1 S2_1 121.9(2) . . ?
S1_1 C1_1 S2_1 119.06(18) . . ?
C1_1 S1_1 Bi1_1 86.31(11) . 4 ?
C1_1 S2_1 Bi1_1 85.95(10) . 4 ?
C7_2 C2_2 C3_2 120.3(3) . . ?
C7_2 C2_2 N1_1 119.3(3) . . ?
C3_2 C2_2 N1_1 120.3(3) . . ?
C2_2 C3_2 C4_2 119.3(3) . . ?
C2_2 C3_2 H3_2 120.3 . . ?
C4_2 C3_2 H3_2 120.3 . . ?
C5_2 C4_2 C3_2 121.5(3) . . ?
C5_2 C4_2 H4_2 119.2 . . ?
C3_2 C4_2 H4_2 119.2 . . ?
C4_2 C5_2 C6_2 118.1(3) . . ?
C4_2 C5_2 C8_2 121.8(3) . . ?
C6_2 C5_2 C8_2 120.0(3) . . ?
C7_2 C6_2 C5_2 121.4(3) . . ?
C7_2 C6_2 H6_2 119.3 . . ?
C5_2 C6_2 H6_2 119.3 . . ?
C6_2 C7_2 C2_2 119.3(3) . . ?
C6_2 C7_2 H7_2 120.3 . . ?
C2_2 C7_2 H7_2 120.3 . . ?
C5_2 C8_2 H8A_2 109.5 . . ?
C5_2 C8_2 H8B_2 109.5 . . ?
H8A_2 C8_2 H8B_2 109.5 . . ?
C5_2 C8_2 H8C_2 109.5 . . ?
H8A_2 C8_2 H8C_2 109.5 . . ?
H8B_2 C8_2 H8C_2 109.5 . . ?
C10_3 C9_3 C14_3 121.5(3) . . ?
C10_3 C9_3 N1_1 116.0(3) . . ?
C14_3 C9_3 N1_1 122.5(3) . . ?
C11_3 C10_3 C9_3 119.6(3) . . ?
C11_3 C10_3 H10_3 120.2 . . ?
C9_3 C10_3 H10_3 120.2 . . ?
C12_3 C11_3 C10_3 121.0(3) . . ?
C12_3 C11_3 H11_3 119.5 . . ?
C10_3 C11_3 H11_3 119.5 . . ?
C11_3 C12_3 C13_3 118.2(3) . . ?
C11_3 C12_3 C15_3 121.7(3) . . ?
C13_3 C12_3 C15_3 120.1(3) . . ?
C12_3 C13_3 C14_3 123.2(3) . . ?
C12_3 C13_3 H13_3 118.4 . . ?
C14_3 C13_3 H13_3 118.4 . . ?
C13_3 C14_3 C9_3 116.4(3) . . ?
C13_3 C14_3 Bi1_1 109.1(2) . . ?
C9_3 C14_3 Bi1_1 134.4(2) . . ?
C12_3 C15_3 H15A_3 109.5 . . ?
C12_3 C15_3 H15B_3 109.5 . . ?
H15A_3 C15_3 H15B_3 109.5 . . ?
C12_3 C15_3 H15C_3 109.5 . . ?
H15A_3 C15_3 H15C_3 109.5 . . ?
H15B_3 C15_3 H15C_3 109.5 . . ?
O2_4 C1_4 H1A_4 109.5 . . ?
O2_4 C1_4 H1B_4 109.5 . . ?
H1A_4 C1_4 H1B_4 109.5 . . ?
O2_4 C1_4 H1C_4 109.5 . . ?
H1A_4 C1_4 H1C_4 109.5 . . ?
H1B_4 C1_4 H1C_4 109.5 . . ?
C3_4 O2_4 C1_4 108.8(16) . . ?
O2_4 C3_4 C4_4 108.9(11) . . ?
O2_4 C3_4 H3A_4 109.9 . . ?
C4_4 C3_4 H3A_4 109.9 . . ?
O2_4 C3_4 H3B_4 109.9 . . ?
C4_4 C3_4 H3B_4 109.9 . . ?
H3A_4 C3_4 H3B_4 108.3 . . ?
O5_4 C4_4 C3_4 109.6(14) . . ?
O5_4 C4_4 H4A_4 109.7 . . ?
C3_4 C4_4 H4A_4 109.7 . . ?
O5_4 C4_4 H4B_4 109.8 . . ?
C3_4 C4_4 H4B_4 109.7 . . ?
H4A_4 C4_4 H4B_4 108.2 . . ?
C6_4 O5_4 C4_4 114.2(16) . . ?
O5_4 C6_4 C7_4 110.2(11) . . ?
O5_4 C6_4 H6A_4 109.6 . . ?
C7_4 C6_4 H6A_4 109.6 . . ?
O5_4 C6_4 H6B_4 109.6 . . ?
C7_4 C6_4 H6B_4 109.6 . . ?
H6A_4 C6_4 H6B_4 108.1 . . ?
C6_4 C7_4 O8_4 117.8(9) . . ?
C6_4 C7_4 H7A_4 107.9 . . ?
O8_4 C7_4 H7A_4 107.8 . . ?
C6_4 C7_4 H7B_4 107.8 . . ?
O8_4 C7_4 H7B_4 107.8 . . ?
H7A_4 C7_4 H7B_4 107.2 . . ?
C9_4 O8_4 C7_4 107.2(8) . . ?
O8_4 C9_4 H9A_4 109.5 . . ?
O8_4 C9_4 H9B_4 109.5 . . ?
H9A_4 C9_4 H9B_4 109.5 . . ?
O8_4 C9_4 H9C_4 109.5 . . ?
H9A_4 C9_4 H9C_4 109.5 . . ?
H9B_4 C9_4 H9C_4 109.5 . . ?
O2_14 C1_14 H1A_14 109.5 . . ?
O2_14 C1_14 H1B_14 109.5 . . ?
H1A_14 C1_14 H1B_14 109.5 . . ?
O2_14 C1_14 H1C_14 109.5 . . ?
H1A_14 C1_14 H1C_14 109.5 . . ?
H1B_14 C1_14 H1C_14 109.5 . . ?
C1_14 O2_14 C3_14 116(2) . . ?
C1_14 O2_14 Bi1_1 121.0(19) . . ?
C3_14 O2_14 Bi1_1 121.7(18) . . ?
O2_14 C3_14 C4_14 110.0(16) . . ?
O2_14 C3_14 H3A_14 109.7 . . ?
C4_14 C3_14 H3A_14 109.7 . . ?
O2_14 C3_14 H3B_14 109.7 . . ?
C4_14 C3_14 H3B_14 109.7 . . ?
H3A_14 C3_14 H3B_14 108.2 . . ?
O5_14 C4_14 C3_14 106(2) . . ?
O5_14 C4_14 H4A_14 110.5 . . ?
C3_14 C4_14 H4A_14 110.5 . . ?
O5_14 C4_14 H4B_14 110.5 . . ?
C3_14 C4_14 H4B_14 110.5 . . ?
H4A_14 C4_14 H4B_14 108.7 . . ?
C4_14 O5_14 C6_14 112(2) . . ?
C7_14 C6_14 O5_14 107.0(16) . . ?
C7_14 C6_14 H6A_14 110.3 . . ?
O5_14 C6_14 H6A_14 110.3 . . ?
C7_14 C6_14 H6B_14 110.3 . . ?
O5_14 C6_14 H6B_14 110.3 . . ?
H6A_14 C6_14 H6B_14 108.6 . . ?
O8_14 C7_14 C6_14 94.0(14) . . ?
O8_14 C7_14 H7A_14 112.9 . . ?
C6_14 C7_14 H7A_14 112.9 . . ?
O8_14 C7_14 H7B_14 112.9 . . ?
C6_14 C7_14 H7B_14 112.9 . . ?
H7A_14 C7_14 H7B_14 110.3 . . ?
C7_14 O8_14 C9_14 98.8(13) . . ?
O8_14 C9_14 H9A_14 109.5 . . ?
O8_14 C9_14 H9B_14 109.5 . . ?
H9A_14 C9_14 H9B_14 109.5 . . ?
O8_14 C9_14 H9C_14 109.5 . . ?
H9A_14 C9_14 H9C_14 109.5 . . ?
H9B_14 C9_14 H9C_14 109.5 . . ?
O6_5 S3_5 O4_5 118.8(14) . . ?
O6_5 S3_5 O5_5 113.5(14) . . ?
O4_5 S3_5 O5_5 107.7(11) . . ?
O6_5 S3_5 C22_5 107.6(10) . . ?
O4_5 S3_5 C22_5 98.5(11) . . ?
O5_5 S3_5 C22_5 109.5(10) . . ?
S3_5 O5_5 Bi1_1 107.6(7) . . ?
F1_5 C22_5 F2_5 108.3(5) . . ?
F1_5 C22_5 F3_5 108.3(5) . . ?
F2_5 C22_5 F3_5 108.1(5) . . ?
F1_5 C22_5 S3_5 111.0(7) . . ?
F2_5 C22_5 S3_5 111.1(8) . . ?
F3_5 C22_5 S3_5 109.9(7) . . ?
O5_15 S3_15 O4_15 120(2) . . ?
O5_15 S3_15 O6_15 117(2) . . ?
O4_15 S3_15 O6_15 113(2) . . ?
O5_15 S3_15 C22_15 92.7(16) . . ?
O4_15 S3_15 C22_15 113(2) . . ?
O6_15 S3_15 C22_15 96.5(15) . . ?
S3_15 O5_15 Bi1_1 106.9(13) . . ?
F1_15 C22_15 F2_15 107.1(11) . . ?
F1_15 C22_15 F3_15 107.7(11) . . ?
F2_15 C22_15 F3_15 108.3(10) . . ?
F1_15 C22_15 S3_15 113.8(12) . . ?
F2_15 C22_15 S3_15 109.2(13) . . ?
F3_15 C22_15 S3_15 110.4(12) . . ?

_refine_diff_density_max         1.714
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.085


####################################################################### 
# 
# 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-Me
_database_code_depnum_ccdc_archive 'CCDC 2223278'
loop_
_audit_author_name
_audit_author_address
'Kai Oberdorf'
;Universitaet Marburg
Germany
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H29 Bi N O2 S O3 C F3'
_chemical_formula_sum            'C23 H29 Bi F3 N O5 S'
_chemical_formula_weight         697.51

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.160(6)
_cell_length_b                   18.258(13)
_cell_length_c                   14.044(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.56(3)
_cell_angle_gamma                90
_cell_volume                     2455(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9212
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      25.04


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    7.324
_shelx_estimated_absorpt_T_min   0.234
_shelx_estimated_absorpt_T_max   0.543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3212
_exptl_absorpt_correction_T_max  0.4286
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0750
0.00 0.00 -1.00 0.0800
-1.00 0.00 0.00 0.0490
1.00 0.00 1.00 0.1250
-1.00 0.00 1.00 0.0850
1.00 0.00 -1.00 0.1340
0.00 -1.00 -1.00 0.0490
1.00 -1.00 -1.00 0.0990
1.00 -1.00 0.00 0.0910
0.00 1.00 0.00 0.0470
0.00 -1.00 0.00 0.0020

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            16184
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4318
_reflns_number_gt                3903
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+2.2500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4318
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_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
Bi1 Bi 0.59506(2) 0.76904(2) 0.59684(2) 0.02166(8) Uani 1 1 d . . . . .
N1 N 0.3811(3) 0.64884(19) 0.6717(3) 0.0270(8) Uani 1 1 d . . . . .
H1 H 0.324299 0.621908 0.692648 0.032 Uiso 1 1 calc R U . . .
F1 F 0.0791(4) 0.5875(2) 0.8251(4) 0.0917(14) Uani 1 1 d . . . . .
S1 S 0.21743(10) 0.47538(6) 0.79393(8) 0.0295(2) Uani 1 1 d . . . . .
O1 O 0.2259(3) 0.51822(19) 0.7093(2) 0.0431(8) Uani 1 1 d . . . . .
C1 C 0.3858(4) 0.7215(2) 0.5232(3) 0.0223(9) Uani 1 1 d . . . . .
O5 O 0.4751(3) 0.86002(17) 0.6604(2) 0.0369(7) Uani 1 1 d . . . . .
O2 O 0.1790(3) 0.39989(18) 0.7719(3) 0.0476(9) Uani 1 1 d . . . . .
F2 F -0.0512(3) 0.5003(3) 0.7434(3) 0.0902(14) Uani 1 1 d . . . . .
C2 C 0.3222(4) 0.6741(2) 0.5728(3) 0.0233(8) Uani 1 1 d . . . . .
O4 O 0.6800(3) 0.65520(15) 0.5326(2) 0.0316(7) Uani 1 1 d . . . . .
C3 C 0.1872(4) 0.6482(2) 0.5191(3) 0.0264(9) Uani 1 1 d . . . . .
H3 H 0.140996 0.616697 0.551542 0.032 Uiso 1 1 calc R U . . .
O3 O 0.3281(3) 0.48793(19) 0.8877(2) 0.0432(8) Uani 1 1 d . . . . .
F3 F 0.0535(3) 0.4909(2) 0.9026(3) 0.0635(9) Uani 1 1 d . . . . .
C6 C 0.3148(4) 0.7409(2) 0.4229(3) 0.0260(9) Uani 1 1 d . . . . .
H6 H 0.358921 0.773516 0.390386 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1831(4) 0.7148(2) 0.3688(3) 0.0277(9) Uani 1 1 d . . . . .
C4 C 0.1213(4) 0.6682(2) 0.4198(3) 0.0294(10) Uani 1 1 d . . . . .
H4 H 0.030640 0.649521 0.385144 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6186(4) 0.7045(2) 0.7330(3) 0.0212(8) Uani 1 1 d . . . . .
C7 C 0.1097(5) 0.7360(3) 0.2605(4) 0.0400(12) Uani 1 1 d . . . . .
H00C H 0.047122 0.696327 0.225726 0.060 Uiso 1 1 calc R U . . .
H00D H 0.178971 0.744851 0.227225 0.060 Uiso 1 1 calc R U . . .
H00E H 0.055267 0.780692 0.258107 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5136(4) 0.6583(2) 0.7439(3) 0.0224(8) Uani 1 1 d . . . . .
C10 C 0.5434(4) 0.6172(2) 0.8332(3) 0.0253(9) Uani 1 1 d . . . . .
H10 H 0.473182 0.586391 0.842347 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6708(4) 0.6206(2) 0.9069(3) 0.0268(9) Uani 1 1 d . . . . .
H11 H 0.687612 0.591825 0.966196 0.032 Uiso 1 1 calc R U . . .
C12 C 0.7787(4) 0.6657(2) 0.8975(3) 0.0267(9) Uani 1 1 d . . . . .
C13 C 0.7482(4) 0.7074(2) 0.8115(3) 0.0253(9) Uani 1 1 d . . . . .
H13 H 0.817722 0.739790 0.804755 0.030 Uiso 1 1 calc R U . . .
C14 C 0.9201(4) 0.6671(3) 0.9796(3) 0.0361(10) Uani 1 1 d . . . . .
H00P H 0.968437 0.620646 0.979537 0.054 Uiso 1 1 calc R U . . .
H00Q H 0.907999 0.674044 1.045324 0.054 Uiso 1 1 calc R U . . .
H00R H 0.975688 0.707527 0.967057 0.054 Uiso 1 1 calc R U . . .
C15 C 0.0668(5) 0.5154(3) 0.8175(4) 0.0481(13) Uani 1 1 d . . . . .
C16 C 0.6352(6) 0.5842(3) 0.5526(5) 0.0553(16) Uani 1 1 d . . . . .
H00S H 0.532777 0.579080 0.520678 0.066 Uiso 1 1 calc R U . . .
H00T H 0.659983 0.576246 0.626273 0.066 Uiso 1 1 calc R U . . .
C17 C 0.7096(5) 0.5304(2) 0.5083(4) 0.0371(11) Uani 1 1 d . . . . .
H00A H 0.652342 0.517690 0.438163 0.045 Uiso 1 1 calc R U . . .
H00B H 0.731835 0.485031 0.549212 0.045 Uiso 1 1 calc R U . . .
C18 C 0.8429(5) 0.5703(3) 0.5110(4) 0.0405(11) Uani 1 1 d . . . . .
H00H H 0.925528 0.549024 0.563110 0.049 Uiso 1 1 calc R U . . .
H00J H 0.856665 0.567471 0.444535 0.049 Uiso 1 1 calc R U . . .
C19 C 0.8199(5) 0.6472(3) 0.5361(6) 0.0624(18) Uani 1 1 d . . . . .
H00W H 0.884271 0.659439 0.604552 0.075 Uiso 1 1 calc R U . . .
H19 H 0.839051 0.680903 0.487160 0.075 Uiso 1 1 calc R U . . .
C20 C 0.3701(5) 0.9083(3) 0.5922(4) 0.0431(12) Uani 1 1 d . . . . .
H00K H 0.315990 0.881963 0.529666 0.052 Uiso 1 1 calc R U . . .
H00O H 0.414781 0.951655 0.573734 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2777(5) 0.9304(3) 0.6508(5) 0.0547(15) Uani 1 1 d . . . . .
H00U H 0.201280 0.894659 0.642100 0.066 Uiso 1 1 calc R U . . .
H00V H 0.237103 0.979625 0.630489 0.066 Uiso 1 1 calc R U . . .
C22 C 0.3779(6) 0.9305(3) 0.7579(5) 0.0618(16) Uani 1 1 d . . . . .
H22 H 0.327671 0.923209 0.806652 0.074 Uiso 1 1 calc R U . . .
H00Z H 0.430398 0.977145 0.773687 0.074 Uiso 1 1 calc R U . . .
C23 C 0.4745(6) 0.8670(3) 0.7610(4) 0.0483(13) Uani 1 1 d . . . . .
H00F H 0.569663 0.877230 0.808147 0.058 Uiso 1 1 calc R U . . .
H00G H 0.439470 0.821601 0.782771 0.058 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 C8 2.190(4) . ?
Bi1 C1 2.207(4) . ?
Bi1 O5 2.402(3) . ?
Bi1 O4 2.529(3) . ?
N1 C2 1.394(5) . ?
N1 C9 1.398(5) . ?
N1 H1 0.8800 . ?
F1 C15 1.323(7) . ?
S1 O3 1.435(3) . ?
S1 O2 1.438(4) . ?
S1 O1 1.449(3) . ?
S1 C15 1.823(5) . ?
C1 C6 1.396(6) . ?
C1 C2 1.397(6) . ?
O5 C23 1.420(6) . ?
O5 C20 1.465(5) . ?
F2 C15 1.327(6) . ?
C2 C3 1.408(5) . ?
O4 C19 1.414(5) . ?
O4 C16 1.433(5) . ?
C3 C4 1.378(6) . ?
C3 H3 0.9500 . ?
F3 C15 1.325(6) . ?
C6 C5 1.384(6) . ?
C6 H6 0.9500 . ?
C5 C4 1.390(6) . ?
C5 C7 1.502(6) . ?
C4 H4 0.9500 . ?
C8 C9 1.408(5) . ?
C8 C13 1.408(5) . ?
C7 H00C 0.9800 . ?
C7 H00D 0.9800 . ?
C7 H00E 0.9800 . ?
C9 C10 1.405(6) . ?
C10 C11 1.362(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.413(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.372(6) . ?
C12 C14 1.512(5) . ?
C13 H13 0.9500 . ?
C14 H00P 0.9800 . ?
C14 H00Q 0.9800 . ?
C14 H00R 0.9800 . ?
C16 C17 1.496(6) . ?
C16 H00S 0.9900 . ?
C16 H00T 0.9900 . ?
C17 C18 1.527(6) . ?
C17 H00A 0.9900 . ?
C17 H00B 0.9900 . ?
C18 C19 1.485(7) . ?
C18 H00H 0.9900 . ?
C18 H00J 0.9900 . ?
C19 H00W 0.9900 . ?
C19 H19 0.9900 . ?
C20 C21 1.497(7) . ?
C20 H00K 0.9900 . ?
C20 H00O 0.9900 . ?
C21 C22 1.507(8) . ?
C21 H00U 0.9900 . ?
C21 H00V 0.9900 . ?
C22 C23 1.510(7) . ?
C22 H22 0.9900 . ?
C22 H00Z 0.9900 . ?
C23 H00F 0.9900 . ?
C23 H00G 0.9900 . ?

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
C8 Bi1 C1 90.21(15) . . ?
C8 Bi1 O5 88.20(13) . . ?
C1 Bi1 O5 85.23(13) . . ?
C8 Bi1 O4 85.32(13) . . ?
C1 Bi1 O4 84.25(12) . . ?
O5 Bi1 O4 167.61(10) . . ?
C2 N1 C9 132.0(3) . . ?
C2 N1 H1 114.0 . . ?
C9 N1 H1 114.0 . . ?
O3 S1 O2 115.0(2) . . ?
O3 S1 O1 115.02(19) . . ?
O2 S1 O1 115.3(2) . . ?
O3 S1 C15 102.5(2) . . ?
O2 S1 C15 103.9(2) . . ?
O1 S1 C15 102.5(2) . . ?
C6 C1 C2 119.4(4) . . ?
C6 C1 Bi1 117.7(3) . . ?
C2 C1 Bi1 123.0(3) . . ?
C23 O5 C20 110.6(3) . . ?
C23 O5 Bi1 127.1(3) . . ?
C20 O5 Bi1 121.4(3) . . ?
N1 C2 C1 125.8(3) . . ?
N1 C2 C3 116.0(3) . . ?
C1 C2 C3 118.1(4) . . ?
C19 O4 C16 106.3(4) . . ?
C19 O4 Bi1 122.1(3) . . ?
C16 O4 Bi1 120.3(3) . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C6 C1 123.1(4) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
C6 C5 C4 116.6(4) . . ?
C6 C5 C7 121.9(4) . . ?
C4 C5 C7 121.5(4) . . ?
C3 C4 C5 122.3(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C9 C8 C13 118.8(4) . . ?
C9 C8 Bi1 123.5(3) . . ?
C13 C8 Bi1 117.6(3) . . ?
C5 C7 H00C 109.5 . . ?
C5 C7 H00D 109.5 . . ?
H00C C7 H00D 109.5 . . ?
C5 C7 H00E 109.5 . . ?
H00C C7 H00E 109.5 . . ?
H00D C7 H00E 109.5 . . ?
N1 C9 C10 116.6(3) . . ?
N1 C9 C8 125.2(4) . . ?
C10 C9 C8 118.2(3) . . ?
C11 C10 C9 121.3(4) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 121.7(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 116.9(4) . . ?
C13 C12 C14 122.6(4) . . ?
C11 C12 C14 120.5(4) . . ?
C12 C13 C8 123.0(4) . . ?
C12 C13 H13 118.5 . . ?
C8 C13 H13 118.5 . . ?
C12 C14 H00P 109.5 . . ?
C12 C14 H00Q 109.5 . . ?
H00P C14 H00Q 109.5 . . ?
C12 C14 H00R 109.5 . . ?
H00P C14 H00R 109.5 . . ?
H00Q C14 H00R 109.5 . . ?
F1 C15 F3 107.3(5) . . ?
F1 C15 F2 107.8(5) . . ?
F3 C15 F2 107.4(4) . . ?
F1 C15 S1 110.6(4) . . ?
F3 C15 S1 111.9(3) . . ?
F2 C15 S1 111.6(4) . . ?
O4 C16 C17 105.9(4) . . ?
O4 C16 H00S 110.5 . . ?
C17 C16 H00S 110.5 . . ?
O4 C16 H00T 110.5 . . ?
C17 C16 H00T 110.5 . . ?
H00S C16 H00T 108.7 . . ?
C16 C17 C18 104.2(4) . . ?
C16 C17 H00A 110.9 . . ?
C18 C17 H00A 110.9 . . ?
C16 C17 H00B 110.9 . . ?
C18 C17 H00B 110.9 . . ?
H00A C17 H00B 108.9 . . ?
C19 C18 C17 104.3(4) . . ?
C19 C18 H00H 110.9 . . ?
C17 C18 H00H 110.9 . . ?
C19 C18 H00J 110.9 . . ?
C17 C18 H00J 110.9 . . ?
H00H C18 H00J 108.9 . . ?
O4 C19 C18 109.0(4) . . ?
O4 C19 H00W 109.9 . . ?
C18 C19 H00W 109.9 . . ?
O4 C19 H19 109.9 . . ?
C18 C19 H19 109.9 . . ?
H00W C19 H19 108.3 . . ?
O5 C20 C21 104.8(4) . . ?
O5 C20 H00K 110.8 . . ?
C21 C20 H00K 110.8 . . ?
O5 C20 H00O 110.8 . . ?
C21 C20 H00O 110.8 . . ?
H00K C20 H00O 108.9 . . ?
C20 C21 C22 102.2(4) . . ?
C20 C21 H00U 111.3 . . ?
C22 C21 H00U 111.3 . . ?
C20 C21 H00V 111.3 . . ?
C22 C21 H00V 111.3 . . ?
H00U C21 H00V 109.2 . . ?
C21 C22 C23 104.1(5) . . ?
C21 C22 H22 110.9 . . ?
C23 C22 H22 110.9 . . ?
C21 C22 H00Z 110.9 . . ?
C23 C22 H00Z 110.9 . . ?
H22 C22 H00Z 109.0 . . ?
O5 C23 C22 105.0(4) . . ?
O5 C23 H00F 110.7 . . ?
C22 C23 H00F 110.7 . . ?
O5 C23 H00G 110.7 . . ?
C22 C23 H00G 110.7 . . ?
H00F C23 H00G 108.8 . . ?

_refine_diff_density_max         0.768
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.121

