# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 1875340'
loop_
_audit_author_name
_audit_author_address
'Crispin Lichtenberg' 'Julius-Maximilians-Universit?t W?rzburg'
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2019-02-28 downloaded from the CCDC.
;
_audit_creation_date             2016-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H19 Bi F3 N3 O4 S'
_chemical_formula_sum            'C24 H19 Bi F3 N3 O4 S'
_chemical_formula_weight         711.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.1161(5)
_cell_length_b                   9.3373(3)
_cell_length_c                   18.4406(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.4741(12)
_cell_angle_gamma                90
_cell_volume                     2438.36(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7779
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.815
_shelx_estimated_absorpt_T_min   0.436
_exptl_absorpt_coefficient_mu    7.376
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0656 before and 0.0247 after correction.
The Ratio of minimum to maximum transmission is 0.8836.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.029
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12418
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.756
_diffrn_reflns_theta_min         2.358
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4112
_reflns_number_total             5190
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.640
_refine_diff_density_min         -1.159
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      0.990
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C23(H23), C8(H8), C9(H9), C5(H5), C14(H14), C11(H11), C12(H12),
 C18(H18), C4(H4), C6(H6), C16(H16), C15(H15), C19(H19), C10(H10), C20(H20),
 C17(H17), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.34007(2) 0.39838(2) 0.03797(2) 0.01353(6) Uani 1 1 d . . . . .
S1 S 0.39166(9) 0.51772(13) -0.14277(7) 0.0169(3) Uani 1 1 d . . . . .
O1 O 0.3071(3) 0.3601(4) 0.20040(18) 0.0227(8) Uani 1 1 d . . . . .
N1 N 0.1782(3) 0.3095(4) 0.0942(2) 0.0147(8) Uani 1 1 d . . . . .
C1 C 0.1400(3) 0.2907(5) 0.0117(3) 0.0146(10) Uani 1 1 d . . . . .
N3 N 0.3877(3) 0.1439(4) 0.0489(2) 0.0186(9) Uani 1 1 d . . . . .
C3 C 0.1618(4) 0.2927(5) -0.1112(3) 0.0177(10) Uani 1 1 d . . . . .
H3 H 0.2007 0.3113 -0.1411 0.021 Uiso 1 1 calc R . . . .
C13 C 0.2716(3) 0.3478(5) 0.1307(3) 0.0158(10) Uani 1 1 d . . . . .
C2 C 0.1966(3) 0.3195(5) -0.0323(2) 0.0132(9) Uani 1 1 d . . . . .
C23 C 0.4549(4) 0.0984(6) 0.1128(3) 0.0264(12) Uani 1 1 d . . . . .
H23 H 0.4787 0.1617 0.1556 0.032 Uiso 1 1 calc R . . . .
C7 C 0.1177(3) 0.2884(5) 0.1394(2) 0.0160(10) Uani 1 1 d . . . . .
F3 F 0.2799(2) 0.5258(4) -0.28855(17) 0.0387(9) Uani 1 1 d . . . . .
F2 F 0.2995(3) 0.7282(4) -0.22920(18) 0.0402(9) Uani 1 1 d . . . . .
O2 O 0.3922(3) 0.6031(4) -0.07778(19) 0.0317(9) Uani 1 1 d . . . . .
F1 F 0.2101(2) 0.5669(5) -0.2074(2) 0.0493(11) Uani 1 1 d . . . . .
O3 O 0.3700(3) 0.3691(4) -0.1374(2) 0.0285(9) Uani 1 1 d . . . . .
O4 O 0.4685(3) 0.5451(5) -0.1702(2) 0.0306(9) Uani 1 1 d . . . . .
C8 C 0.0618(4) 0.4020(6) 0.1471(3) 0.0213(11) Uani 1 1 d . . . . .
H8 H 0.0653 0.4928 0.1250 0.026 Uiso 1 1 calc R . . . .
C9 C 0.0011(4) 0.3802(6) 0.1874(3) 0.0224(11) Uani 1 1 d . . . . .
H9 H -0.0370 0.4569 0.1936 0.027 Uiso 1 1 calc R . . . .
C5 C 0.0146(3) 0.2153(5) -0.1036(3) 0.0174(10) Uani 1 1 d . . . . .
H5 H -0.0482 0.1818 -0.1283 0.021 Uiso 1 1 calc R . . . .
C14 C 0.2020(4) 0.6975(6) -0.0238(3) 0.0200(11) Uani 1 1 d . . . . .
H14 H 0.1884 0.6495 -0.0719 0.024 Uiso 1 1 calc R . . . .
C24 C 0.2897(4) 0.5867(6) -0.2212(3) 0.0238(12) Uani 1 1 d . . . . .
C11 C 0.0516(4) 0.1364(5) 0.2121(3) 0.0165(10) Uani 1 1 d . . . . .
H11 H 0.0479 0.0460 0.2345 0.020 Uiso 1 1 calc R . . . .
C12 C 0.1140(3) 0.1562(5) 0.1724(3) 0.0144(10) Uani 1 1 d . . . . .
H12 H 0.1535 0.0800 0.1679 0.017 Uiso 1 1 calc R . . . .
C18 C 0.2739(4) 0.6991(6) 0.1077(3) 0.0219(11) Uani 1 1 d . . . . .
H18 H 0.3119 0.6524 0.1538 0.026 Uiso 1 1 calc R . . . .
C4 C 0.0716(4) 0.2393(5) -0.1474(3) 0.0179(10) Uani 1 1 d . . . . .
H4 H 0.0490 0.2193 -0.2013 0.021 Uiso 1 1 calc R . . . .
C6 C 0.0483(4) 0.2398(5) -0.0241(3) 0.0187(11) Uani 1 1 d . . . . .
H6 H 0.0091 0.2221 0.0055 0.022 Uiso 1 1 calc R . . . .
N2 N 0.2558(3) 0.6302(4) 0.0406(2) 0.0162(9) Uani 1 1 d . . . . .
C16 C 0.1858(4) 0.9013(6) 0.0465(3) 0.0242(11) Uani 1 1 d . . . . .
H16 H 0.1620 0.9948 0.0484 0.029 Uiso 1 1 calc R . . . .
C15 C 0.1655(4) 0.8317(6) -0.0241(3) 0.0219(11) Uani 1 1 d . . . . .
H15 H 0.1275 0.8759 -0.0711 0.026 Uiso 1 1 calc R . . . .
C19 C 0.3548(4) 0.0540(6) -0.0117(3) 0.0221(11) Uani 1 1 d . . . . .
H19 H 0.3070 0.0867 -0.0575 0.027 Uiso 1 1 calc R . . . .
C10 C -0.0045(4) 0.2478(6) 0.2188(3) 0.0197(11) Uani 1 1 d . . . . .
H10 H -0.0475 0.2335 0.2453 0.024 Uiso 1 1 calc R . . . .
C20 C 0.3882(4) -0.0838(6) -0.0094(3) 0.0255(12) Uani 1 1 d . . . . .
H20 H 0.3643 -0.1448 -0.0532 0.031 Uiso 1 1 calc R . . . .
C17 C 0.2407(4) 0.8337(6) 0.1137(3) 0.0272(13) Uani 1 1 d . . . . .
H17 H 0.2550 0.8790 0.1626 0.033 Uiso 1 1 calc R . . . .
C21 C 0.4561(4) -0.1313(6) 0.0568(3) 0.0304(14) Uani 1 1 d . . . . .
H21 H 0.4790 -0.2268 0.0603 0.037 Uiso 1 1 calc R . . . .
C22 C 0.4912(4) -0.0387(7) 0.1187(3) 0.0322(14) Uani 1 1 d . . . . .
H22 H 0.5398 -0.0689 0.1647 0.039 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N3 2.471(4) . ?
Bi1 C13 2.335(5) . ?
Bi1 C2 2.227(5) . ?
Bi1 O2 3.164(4) . ?
Bi1 N2 2.520(4) . ?
S1 O2 1.437(4) . ?
S1 O3 1.437(4) . ?
S1 O4 1.443(4) . ?
S1 C24 1.823(5) . ?
O1 C13 1.213(5) . ?
N1 C1 1.437(5) . ?
N1 C13 1.382(6) . ?
N1 C7 1.452(6) . ?
C1 C2 1.395(6) . ?
C1 C6 1.394(7) . ?
N3 C23 1.328(6) . ?
N3 C19 1.346(6) . ?
C3 C2 1.387(6) . ?
C3 C4 1.386(7) . ?
C23 C22 1.382(8) . ?
C7 C8 1.394(7) . ?
C7 C12 1.385(7) . ?
F3 C24 1.326(6) . ?
F2 C24 1.344(6) . ?
F1 C24 1.327(6) . ?
C8 C9 1.383(7) . ?
C9 C10 1.380(7) . ?
C5 C4 1.390(7) . ?
C5 C6 1.393(6) . ?
C14 N2 1.337(6) . ?
C14 C15 1.369(7) . ?
C11 C12 1.394(7) . ?
C11 C10 1.375(7) . ?
C18 N2 1.335(6) . ?
C18 C17 1.372(7) . ?
C16 C15 1.390(7) . ?
C16 C17 1.379(7) . ?
C19 C20 1.377(7) . ?
C20 C21 1.366(8) . ?
C21 C22 1.381(8) . ?

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
N3 Bi1 O2 120.14(11) . . ?
N3 Bi1 N2 163.56(13) . . ?
C13 Bi1 N3 86.36(15) . . ?
C13 Bi1 O2 153.50(14) . . ?
C13 Bi1 N2 78.67(15) . . ?
C2 Bi1 N3 85.77(15) . . ?
C2 Bi1 C13 76.60(16) . . ?
C2 Bi1 O2 103.25(14) . . ?
C2 Bi1 N2 84.21(15) . . ?
N2 Bi1 O2 74.98(11) . . ?
O2 S1 O3 114.4(2) . . ?
O2 S1 O4 115.0(2) . . ?
O2 S1 C24 102.9(2) . . ?
O3 S1 O4 115.2(3) . . ?
O3 S1 C24 104.2(2) . . ?
O4 S1 C24 102.7(2) . . ?
C1 N1 C7 119.5(4) . . ?
C13 N1 C1 120.7(4) . . ?
C13 N1 C7 119.8(4) . . ?
C2 C1 N1 119.4(4) . . ?
C6 C1 N1 120.5(4) . . ?
C6 C1 C2 120.1(4) . . ?
C23 N3 Bi1 119.4(3) . . ?
C23 N3 C19 118.9(5) . . ?
C19 N3 Bi1 121.3(3) . . ?
C4 C3 C2 121.2(4) . . ?
O1 C13 Bi1 127.7(4) . . ?
O1 C13 N1 122.6(4) . . ?
N1 C13 Bi1 109.5(3) . . ?
C1 C2 Bi1 113.4(3) . . ?
C3 C2 Bi1 127.2(3) . . ?
C3 C2 C1 119.4(4) . . ?
N3 C23 C22 121.6(5) . . ?
C8 C7 N1 118.8(4) . . ?
C12 C7 N1 120.2(4) . . ?
C12 C7 C8 121.0(4) . . ?
S1 O2 Bi1 107.29(19) . . ?
C9 C8 C7 118.8(5) . . ?
C10 C9 C8 120.4(5) . . ?
C4 C5 C6 120.8(4) . . ?
N2 C14 C15 123.6(4) . . ?
F3 C24 S1 112.3(4) . . ?
F3 C24 F2 107.4(4) . . ?
F3 C24 F1 107.9(5) . . ?
F2 C24 S1 109.9(4) . . ?
F1 C24 S1 111.7(3) . . ?
F1 C24 F2 107.5(5) . . ?
C10 C11 C12 119.9(4) . . ?
C7 C12 C11 119.1(5) . . ?
N2 C18 C17 123.6(5) . . ?
C3 C4 C5 119.0(4) . . ?
C5 C6 C1 119.4(5) . . ?
C14 N2 Bi1 122.8(3) . . ?
C18 N2 Bi1 119.4(3) . . ?
C18 N2 C14 117.3(4) . . ?
C17 C16 C15 119.6(5) . . ?
C14 C15 C16 117.9(4) . . ?
N3 C19 C20 122.2(5) . . ?
C11 C10 C9 120.7(5) . . ?
C21 C20 C19 118.9(5) . . ?
C18 C17 C16 118.0(5) . . ?
C20 C21 C22 119.1(5) . . ?
C21 C22 C23 119.3(5) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_5
_database_code_depnum_ccdc_archive 'CCDC 1875343'
loop_
_audit_author_name
_audit_author_address
'Crispin Lichtenberg' 'Julius-Maximilians-Universit?t W?rzburg'
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2019-02-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34.2 H30.2 Bi F3 N4.44 O3 S, 0.56(C5 H5 N)'
_chemical_formula_sum            'C37 H33 Bi F3 N5 O3 S'
_chemical_formula_weight         893.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2452(6)
_cell_length_b                   16.0336(7)
_cell_length_c                   19.9108(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.575(2)
_cell_angle_gamma                90
_cell_volume                     3566.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.494
_shelx_estimated_absorpt_T_min   0.298
_exptl_absorpt_coefficient_mu    5.062
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0687 before and 0.0450 after correction. The Ratio of minimum to maximum transmission is 0.7746. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.162
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51137
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.781
_diffrn_reflns_theta_min         2.222
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6971
_reflns_number_total             7585
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.202
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         7585
_refine_ls_number_restraints     213
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.215
_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)+(0.0032P)²+17.1504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C32
 1.84 with sigma of 0.02
 F3-C32
 1.3 with sigma of 0.02
 F1-C32
 1.3 with sigma of 0.02
 H22_$9-H33A
 2.02 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F1) \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.008
Uanis(C32) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(C10) \\sim Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.016
Uanis(N1A) = Uanis(N1)
4. Rigid body (RIGU) restrains
 C36, C35, C34, C33, C37, N5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C12, C11, C10, C9, C8, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1A, C7A, C8A, C9A, C10A, C11A, C12A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, F2A, F3A, C32A, S1, O3A, O2A, O1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C37A, C36A, C35A, C34A, C33A, N5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C7)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=Sof(C10)=Sof(H10)=Sof(C9)=Sof(H9)=
 Sof(C8)=Sof(H8)=Sof(N1)=1-FVAR(1)
 Sof(N1A)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
 Sof(C36)=Sof(H36)=Sof(C35)=Sof(H35)=Sof(C34)=Sof(H34)=Sof(C33)=Sof(H33)=
 Sof(C37)=Sof(H37)=Sof(N5)=1-FVAR(2)
 Sof(C37A)=Sof(H37A)=Sof(C36A)=Sof(H36A)=Sof(C35A)=Sof(H35A)=Sof(C34A)=
 Sof(H34A)=Sof(C33A)=Sof(H33A)=Sof(N5A)=FVAR(2)
 Sof(O3)=Sof(S1A)=Sof(O2)=Sof(O1)=1-FVAR(3)
 Sof(S1)=Sof(O3A)=Sof(O2A)=Sof(O1A)=FVAR(3)
 Sof(C32)=Sof(F3)=Sof(F1)=Sof(F2)=1-FVAR(4)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C32A)=FVAR(4)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C18(H18), C27(H27), C4(H4), C22(H22), C26(H26),
 C28(H28), C31(H31), C23(H23), C16(H16), C24(H24), C17(H17), C29(H29), C30(H30),
  C25(H25), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C12(H12),
 C11(H11), C10(H10), C9(H9), C8(H8), C37A(H37A), C36A(H36A), C35A(H35A),
 C34A(H34A), C33A(H33A), C36(H36), C35(H35), C34(H34), C33(H33), C37(H37)
6.b Fitted hexagon refined as free rotating group:
 C7A(C8A,C9A,C10A,C11A,C12A), C37A(C36A,C35A,C34A,C33A,N5A)
6.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
;
_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 0.33634(2) 0.64305(2) 0.76710(2) 0.01793(5) Uani 1 1 d . . . . .
N2 N 0.1014(3) 0.5879(3) 0.66502(19) 0.0267(9) Uani 1 1 d . . . . .
C2 C 0.4643(4) 0.6075(3) 0.6962(2) 0.0172(8) Uani 1 1 d . . . . .
N3 N 0.3296(4) 0.7812(2) 0.7076(2) 0.0307(9) Uani 1 1 d . . . . .
C1 C 0.4096(4) 0.5732(3) 0.6362(2) 0.0244(9) Uani 1 1 d . . . . .
N1A N 0.283(2) 0.5787(9) 0.6220(9) 0.018(2) Uani 0.482(7) 1 d . U P A 1
C3 C 0.5882(4) 0.6178(3) 0.7059(2) 0.0191(8) Uani 1 1 d . . . . .
H3 H 0.625175 0.641878 0.746632 0.023 Uiso 1 1 calc R . . . .
N4 N 0.3491(3) 0.4953(2) 0.8054(2) 0.0271(8) Uani 1 1 d . . . . .
C13 C 0.2147(4) 0.5930(3) 0.6752(2) 0.0204(9) Uani 1 1 d . . . . .
C19 C -0.0037(4) 0.5651(3) 0.7642(2) 0.0273(10) Uani 1 1 d . . . . .
C14 C 0.0318(4) 0.6181(3) 0.7149(2) 0.0199(9) Uani 1 1 d . . . . .
C5 C 0.6034(4) 0.5574(3) 0.5974(2) 0.0287(10) Uani 1 1 d . . . . .
H5 H 0.651007 0.539611 0.563656 0.034 Uiso 1 1 calc R . . . .
C6 C 0.4808(4) 0.5470(4) 0.5867(2) 0.0336(12) Uani 1 1 d . . . . .
H6 H 0.444758 0.522298 0.546034 0.040 Uiso 1 1 calc R . . . .
C18 C -0.0772(5) 0.5982(4) 0.8097(3) 0.0398(13) Uani 1 1 d . . . . .
H18 H -0.101345 0.563472 0.844289 0.048 Uiso 1 1 calc R . . . .
C15 C -0.0113(4) 0.7015(3) 0.7087(3) 0.0320(11) Uani 1 1 d . . . . .
C27 C 0.3639(4) 0.4296(3) 0.7658(3) 0.0315(11) Uani 1 1 d . . . . .
H27 H 0.378795 0.439348 0.720415 0.038 Uiso 1 1 calc R . . . .
C4 C 0.6582(4) 0.5928(3) 0.6558(2) 0.0234(9) Uani 1 1 d . . . . .
H4 H 0.742581 0.600168 0.662061 0.028 Uiso 1 1 calc R . . . .
C22 C 0.3017(5) 0.8469(3) 0.7439(4) 0.0502(16) Uani 1 1 d . . . . .
H22 H 0.282929 0.837968 0.788679 0.060 Uiso 1 1 calc DR . . . .
C21 C 0.0325(5) 0.4752(3) 0.7670(3) 0.0433(14) Uani 1 1 d . . . . .
H21A H 0.021358 0.451565 0.721294 0.065 Uiso 1 1 calc GR . . . .
H21B H -0.017098 0.444601 0.796029 0.065 Uiso 1 1 calc GR . . . .
H21C H 0.116860 0.470605 0.785384 0.065 Uiso 1 1 calc GR . . . .
F1A F 0.3758(6) 0.7614(5) 0.9179(3) 0.077(2) Uani 0.670(6) 1 d . U P B 2
C26 C 0.3548(5) 0.7950(3) 0.6448(3) 0.0390(13) Uani 1 1 d . . . . .
H26 H 0.373803 0.749018 0.617884 0.047 Uiso 1 1 calc R . . . .
F2A F 0.5187(9) 0.8315(6) 0.9539(5) 0.092(3) Uani 0.670(6) 1 d . U P B 2
C28 C 0.3585(5) 0.3478(3) 0.7882(4) 0.0470(15) Uani 1 1 d . . . . .
H28 H 0.368736 0.302505 0.758710 0.056 Uiso 1 1 calc R . . . .
C31 C 0.3294(5) 0.4806(4) 0.8688(3) 0.0408(13) Uani 1 1 d . . . . .
H31 H 0.318597 0.526733 0.897377 0.049 Uiso 1 1 calc R . . . .
C23 C 0.2991(6) 0.9274(4) 0.7189(5) 0.065(2) Uani 1 1 d . . . . .
H23 H 0.278357 0.972620 0.746160 0.079 Uiso 1 1 calc R . . . .
C20 C 0.0167(5) 0.7554(4) 0.6507(4) 0.0516(17) Uani 1 1 d . . . . .
H20A H 0.098724 0.776557 0.659752 0.077 Uiso 1 1 calc GR . . . .
H20B H -0.039354 0.802326 0.645542 0.077 Uiso 1 1 calc GR . . . .
H20C H 0.008995 0.722271 0.609065 0.077 Uiso 1 1 calc GR . . . .
C16 C -0.0835(5) 0.7296(4) 0.7557(4) 0.0489(16) Uani 1 1 d . . . . .
H16 H -0.111808 0.785491 0.753076 0.059 Uiso 1 1 calc R . . . .
C24 C 0.3260(6) 0.9414(4) 0.6557(5) 0.068(2) Uani 1 1 d . . . . .
H24 H 0.325653 0.996363 0.637831 0.081 Uiso 1 1 calc R . . . .
C17 C -0.1150(5) 0.6789(4) 0.8057(4) 0.0555(18) Uani 1 1 d . . . . .
H17 H -0.163542 0.699945 0.837912 0.067 Uiso 1 1 calc R . . . .
C29 C 0.3382(6) 0.3340(4) 0.8536(4) 0.059(2) Uani 1 1 d . . . . .
H29 H 0.333950 0.278656 0.870146 0.071 Uiso 1 1 calc R . . . .
C30 C 0.3240(6) 0.4007(4) 0.8951(4) 0.0596(19) Uani 1 1 d . . . . .
H30 H 0.310782 0.392398 0.940937 0.071 Uiso 1 1 calc R . . . .
C25 C 0.3541(6) 0.8744(4) 0.6176(4) 0.0602(19) Uani 1 1 d . . . . .
H25 H 0.372923 0.882490 0.572702 0.072 Uiso 1 1 calc R . . . .
F3A F 0.4842(8) 0.7350(6) 1.0118(3) 0.116(4) Uani 0.670(6) 1 d . U P B 2
C32A C 0.4874(9) 0.7600(7) 0.9489(4) 0.048(2) Uani 0.670(6) 1 d . U P B 2
C7A C 0.2219(5) 0.5627(4) 0.5559(2) 0.0216(19) Uani 0.482(7) 1 d . U P A 1
C8A C 0.2065(6) 0.6279(3) 0.5097(3) 0.033(2) Uani 0.482(7) 1 d G U P A 1
H8A H 0.235837 0.681924 0.522051 0.040 Uiso 0.482(7) 1 calc R . P A 1
C9A C 0.1481(6) 0.6139(5) 0.4453(3) 0.041(3) Uani 0.482(7) 1 d G U P A 1
H9A H 0.137546 0.658399 0.413657 0.049 Uiso 0.482(7) 1 calc R . P A 1
C10A C 0.1051(6) 0.5348(5) 0.4271(3) 0.039(3) Uani 0.482(7) 1 d G U P A 1
H10A H 0.065233 0.525242 0.383135 0.047 Uiso 0.482(7) 1 calc R . P A 1
C11A C 0.1206(7) 0.4697(4) 0.4734(4) 0.036(3) Uani 0.482(7) 1 d G U P A 1
H11A H 0.091211 0.415609 0.461007 0.044 Uiso 0.482(7) 1 calc R . P A 1
C12A C 0.1790(7) 0.4836(4) 0.5378(3) 0.031(2) Uani 0.482(7) 1 d G U P A 1
H12A H 0.189502 0.439133 0.569402 0.037 Uiso 0.482(7) 1 calc R . P A 1
C7 C 0.2300(7) 0.5061(6) 0.5722(5) 0.0226(18) Uani 0.518(7) 1 d . U P A 2
C12 C 0.2246(8) 0.4205(6) 0.5760(5) 0.030(2) Uani 0.518(7) 1 d . U P A 2
H12 H 0.258781 0.392614 0.615663 0.036 Uiso 0.518(7) 1 calc R . P A 2
C11 C 0.1698(9) 0.3749(7) 0.5223(6) 0.041(2) Uani 0.518(7) 1 d . U P A 2
H11 H 0.166662 0.315785 0.524789 0.049 Uiso 0.518(7) 1 calc R . P A 2
C10 C 0.1207(9) 0.4149(9) 0.4661(6) 0.043(2) Uani 0.518(7) 1 d . U P A 2
H10 H 0.082970 0.383296 0.429299 0.052 Uiso 0.518(7) 1 calc R . P A 2
C9 C 0.1242(11) 0.4992(10) 0.4611(7) 0.037(3) Uani 0.518(7) 1 d . U P A 2
H9 H 0.088389 0.525957 0.421225 0.045 Uiso 0.518(7) 1 calc R . P A 2
C8 C 0.1825(8) 0.5485(7) 0.5163(5) 0.033(2) Uani 0.518(7) 1 d . U P A 2
H8 H 0.187279 0.607512 0.513586 0.040 Uiso 0.518(7) 1 calc R . P A 2
N1 N 0.286(2) 0.5523(8) 0.6302(9) 0.018(2) Uani 0.518(7) 1 d . U P A 2
C37A C 0.2237(16) 0.7836(12) 0.4543(8) 0.164(12) Uani 0.441(6) 1 d . U P C 2
H37A H 0.291813 0.814059 0.473359 0.197 Uiso 0.441(6) 1 calc R . P C 2
C36A C 0.1131(19) 0.7969(9) 0.4773(7) 0.127(9) Uani 0.441(6) 1 d G U P C 2
H36A H 0.105628 0.836391 0.512075 0.152 Uiso 0.441(6) 1 calc R . P C 2
C35A C 0.0135(14) 0.7523(9) 0.4493(7) 0.105(7) Uani 0.441(6) 1 d G U P C 2
H35A H -0.062087 0.761406 0.465020 0.126 Uiso 0.441(6) 1 calc R . P C 2
C34A C 0.0245(10) 0.6945(9) 0.3984(6) 0.104(7) Uani 0.441(6) 1 d G U P C 2
H34A H -0.043619 0.664088 0.379249 0.124 Uiso 0.441(6) 1 calc R . P C 2
C33A C 0.1351(11) 0.6813(8) 0.3754(6) 0.101(7) Uani 0.441(6) 1 d G U P C 2
H33A H 0.142565 0.641755 0.340532 0.122 Uiso 0.441(6) 1 calc DR . P C 2
N5A N 0.2347(11) 0.7258(11) 0.4033(8) 0.180(12) Uani 0.441(6) 1 d G U P C 2
C36 C 0.002(3) 0.9652(18) 0.5187(12) 0.139(8) Uani 0.559(6) 1 d . U P C -1
H36 H -0.045336 1.003720 0.540314 0.166 Uiso 0.559(6) 1 calc R . P C -1
C35 C -0.0513(17) 0.8960(15) 0.5084(9) 0.104(6) Uani 0.559(6) 1 d . U P C -1
H35 H -0.130694 0.885497 0.518084 0.125 Uiso 0.559(6) 1 calc R . P C -1
C34 C 0.0221(19) 0.8361(18) 0.4808(10) 0.124(7) Uani 0.559(6) 1 d . U P C -1
H34 H -0.001971 0.779775 0.472999 0.148 Uiso 0.559(6) 1 calc R . P C -1
C33 C 0.1278(19) 0.8652(16) 0.4667(10) 0.109(6) Uani 0.559(6) 1 d . U P C -1
H33 H 0.178827 0.827975 0.446294 0.131 Uiso 0.559(6) 1 calc R . P C -1
C37 C 0.101(2) 0.9967(16) 0.5080(9) 0.108(6) Uani 0.559(6) 1 d . U P C -1
H37 H 0.124118 1.052354 0.519341 0.129 Uiso 0.559(6) 1 calc R . P C -1
N5 N 0.167(2) 0.9429(14) 0.4792(11) 0.159(8) Uani 0.559(6) 1 d . U P C -1
S1 S 0.5868(10) 0.6851(7) 0.9169(5) 0.045(2) Uani 0.599(13) 1 d . U P B 1
O3A O 0.6944(6) 0.6926(7) 0.9442(3) 0.041(2) Uani 0.599(13) 1 d . U P B 2
O2A O 0.5787(10) 0.7385(7) 0.8395(5) 0.049(3) Uani 0.599(13) 1 d . U P B 2
O1A O 0.5211(7) 0.6160(4) 0.8968(6) 0.066(4) Uani 0.599(13) 1 d . U P B 2
O3 O 0.7037(13) 0.6355(14) 0.9353(8) 0.077(5) Uani 0.401(13) 1 d . . P B 1
S1A S 0.5819(11) 0.6927(7) 0.8996(5) 0.0215(17) Uani 0.401(13) 1 d D . P B 2
O2 O 0.5016(12) 0.6510(9) 0.9588(9) 0.088(7) Uani 0.401(13) 1 d . . P B 1
O1 O 0.5550(13) 0.6931(14) 0.8494(8) 0.065(6) Uani 0.401(13) 1 d . . P B 1
C32 C 0.641(2) 0.7799(14) 0.9461(10) 0.068(6) Uani 0.330(6) 1 d D U P B 1
F3 F 0.6945(15) 0.7819(10) 1.0081(8) 0.096(5) Uani 0.330(6) 1 d D U P B 1
F1 F 0.5712(18) 0.8417(10) 0.9424(10) 0.079(5) Uani 0.330(6) 1 d D U P B 1
F2 F 0.7134(19) 0.8104(9) 0.9051(9) 0.116(7) Uani 0.330(6) 1 d . . P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C2 2.202(4) . ?
Bi1 N3 2.510(4) . ?
Bi1 N4 2.488(4) . ?
Bi1 C13 2.299(4) . ?
Bi1 O1A 3.154(9) . ?
Bi1 O1 2.907(15) . ?
N2 C13 1.269(6) . ?
N2 C14 1.419(5) . ?
C2 C1 1.394(6) . ?
C2 C3 1.394(6) . ?
N3 C22 1.335(7) . ?
N3 C26 1.332(7) . ?
C1 N1A 1.43(3) . ?
C1 C6 1.402(6) . ?
C1 N1 1.42(2) . ?
N1A C13 1.39(2) . ?
N1A C7A 1.433(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(6) . ?
N4 C27 1.337(6) . ?
N4 C31 1.327(6) . ?
C13 N1 1.43(2) . ?
C19 C14 1.391(6) . ?
C19 C18 1.398(7) . ?
C19 C21 1.497(7) . ?
C14 C15 1.423(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(6) . ?
C5 C4 1.375(6) . ?
C6 H6 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.361(9) . ?
C15 C20 1.504(8) . ?
C15 C16 1.383(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.389(7) . ?
C4 H4 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.383(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
F1A C32A 1.334(11) . ?
F1A N5A 1.59(8) 4_576 ?
C26 H26 0.9500 . ?
C26 C25 1.382(8) . ?
F2A C32A 1.201(13) . ?
C28 H28 0.9500 . ?
C28 C29 1.364(10) . ?
C31 H31 0.9500 . ?
C31 C30 1.388(8) . ?
C23 H23 0.9500 . ?
C23 C24 1.348(11) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.364(9) . ?
C24 H24 0.9500 . ?
C24 C25 1.373(11) . ?
C17 H17 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.373(10) . ?
C30 H30 0.9500 . ?
C25 H25 0.9500 . ?
F3A C32A 1.320(10) . ?
C32A S1A 1.869(14) . ?
C7A C8A 1.3900 . ?
C7A C12A 1.3900 . ?
C8A H8A 0.9500 . ?
C8A C9A 1.3900 . ?
C9A H9A 0.9500 . ?
C9A C10A 1.3900 . ?
C10A H10A 0.9500 . ?
C10A C11A 1.3900 . ?
C11A H11A 0.9500 . ?
C11A C12A 1.3900 . ?
C12A H12A 0.9500 . ?
C7 C12 1.376(14) . ?
C7 C8 1.361(14) . ?
C7 N1 1.454(19) . ?
C12 H12 0.9500 . ?
C12 C11 1.380(13) . ?
C11 H11 0.9500 . ?
C11 C10 1.351(17) . ?
C10 H10 0.9500 . ?
C10 C9 1.36(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.448(17) . ?
C8 H8 0.9500 . ?
C37A H37A 0.9500 . ?
C37A C36A 1.3900 . ?
C37A N5A 1.3900 . ?
C36A H36A 0.9500 . ?
C36A C35A 1.3900 . ?
C35A H35A 0.9500 . ?
C35A C34A 1.3900 . ?
C34A H34A 0.9500 . ?
C34A C33A 1.3900 . ?
C33A H33A 0.9500 . ?
C33A N5A 1.3900 . ?
C36 H36 0.9500 . ?
C36 C35 1.27(3) . ?
C36 C37 1.26(3) . ?
C35 H35 0.9500 . ?
C35 C34 1.42(3) . ?
C34 H34 0.9500 . ?
C34 C33 1.34(3) . ?
C33 H33 0.9500 . ?
C33 N5 1.33(3) . ?
C37 H37 0.9500 . ?
C37 N5 1.31(3) . ?
S1 O3 1.545(19) . ?
S1 O2 1.448(15) . ?
S1 O1 1.356(17) . ?
S1 C32 1.71(3) . ?
O3A S1A 1.461(14) . ?
O2A S1A 1.400(12) . ?
O1A S1A 1.405(16) . ?
C32 F3 1.310(16) . ?
C32 F1 1.260(17) . ?
C32 F2 1.31(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Bi1 N3 84.96(14) . . ?
C2 Bi1 N4 86.06(14) . . ?
C2 Bi1 C13 76.89(15) . . ?
C2 Bi1 O1A 94.1(2) . . ?
C2 Bi1 O1 82.0(3) . . ?
N3 Bi1 O1A 119.31(16) . . ?
N3 Bi1 O1 90.0(5) . . ?
N4 Bi1 N3 169.41(13) . . ?
N4 Bi1 O1A 66.96(16) . . ?
N4 Bi1 O1 94.3(5) . . ?
C13 Bi1 N3 87.08(15) . . ?
C13 Bi1 N4 85.41(15) . . ?
C13 Bi1 O1A 151.60(17) . . ?
C13 Bi1 O1 158.8(3) . . ?
C13 N2 C14 119.3(4) . . ?
C1 C2 Bi1 113.3(3) . . ?
C1 C2 C3 120.0(4) . . ?
C3 C2 Bi1 126.7(3) . . ?
C22 N3 Bi1 115.9(4) . . ?
C26 N3 Bi1 126.3(3) . . ?
C26 N3 C22 117.8(5) . . ?
C2 C1 N1A 118.6(9) . . ?
C2 C1 C6 119.3(4) . . ?
C2 C1 N1 119.7(8) . . ?
C6 C1 N1A 121.2(9) . . ?
C6 C1 N1 120.2(8) . . ?
C1 N1A C7A 122.1(18) . . ?
C13 N1A C1 118.8(13) . . ?
C13 N1A C7A 118.9(18) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C27 N4 Bi1 125.1(3) . . ?
C31 N4 Bi1 116.8(3) . . ?
C31 N4 C27 117.8(5) . . ?
N2 C13 Bi1 130.2(3) . . ?
N2 C13 N1A 119.6(9) . . ?
N2 C13 N1 119.6(9) . . ?
N1A C13 Bi1 109.6(9) . . ?
N1 C13 Bi1 109.5(8) . . ?
C14 C19 C18 117.6(5) . . ?
C14 C19 C21 121.0(4) . . ?
C18 C19 C21 121.3(5) . . ?
N2 C14 C15 118.1(4) . . ?
C19 C14 N2 120.8(4) . . ?
C19 C14 C15 120.8(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(4) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 H6 120.1 . . ?
C19 C18 H18 119.1 . . ?
C17 C18 C19 121.8(5) . . ?
C17 C18 H18 119.1 . . ?
C14 C15 C20 120.4(5) . . ?
C16 C15 C14 117.9(5) . . ?
C16 C15 C20 121.5(5) . . ?
N4 C27 H27 118.7 . . ?
N4 C27 C28 122.7(5) . . ?
C28 C27 H27 118.7 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
N3 C22 H22 118.7 . . ?
N3 C22 C23 122.5(7) . . ?
C23 C22 H22 118.7 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C32A F1A N5A 162.0(14) . 4_576 ?
N3 C26 H26 119.0 . . ?
N3 C26 C25 121.9(6) . . ?
C25 C26 H26 119.0 . . ?
C27 C28 H28 120.7 . . ?
C29 C28 C27 118.6(6) . . ?
C29 C28 H28 120.7 . . ?
N4 C31 H31 118.6 . . ?
N4 C31 C30 122.9(6) . . ?
C30 C31 H31 118.6 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(7) . . ?
C24 C23 H23 120.2 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.4(5) . . ?
C17 C16 H16 119.3 . . ?
C23 C24 H24 120.8 . . ?
C23 C24 C25 118.5(6) . . ?
C25 C24 H24 120.8 . . ?
C18 C17 C16 120.2(5) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C28 C29 H29 120.3 . . ?
C28 C29 C30 119.5(5) . . ?
C30 C29 H29 120.3 . . ?
C31 C30 H30 120.7 . . ?
C29 C30 C31 118.5(6) . . ?
C29 C30 H30 120.7 . . ?
C26 C25 H25 120.2 . . ?
C24 C25 C26 119.7(7) . . ?
C24 C25 H25 120.2 . . ?
F1A C32A S1A 109.2(7) . . ?
F2A C32A F1A 105.9(10) . . ?
F2A C32A F3A 104.5(10) . . ?
F2A C32A S1A 114.6(9) . . ?
F3A C32A F1A 108.5(9) . . ?
F3A C32A S1A 113.7(8) . . ?
C8A C7A N1A 119.0(7) . . ?
C8A C7A C12A 120.0 . . ?
C12A C7A N1A 121.0(7) . . ?
C7A C8A H8A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C10A C11A C12A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C7A C12A H12A 120.0 . . ?
C11A C12A C7A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12 C7 N1 118.9(9) . . ?
C8 C7 C12 121.8(10) . . ?
C8 C7 N1 119.2(10) . . ?
C7 C12 H12 119.9 . . ?
C7 C12 C11 120.3(10) . . ?
C11 C12 H12 119.9 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.6(11) . . ?
C10 C11 H11 120.2 . . ?
C11 C10 H10 119.3 . . ?
C11 C10 C9 121.4(11) . . ?
C9 C10 H10 119.3 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.1(13) . . ?
C8 C9 H9 119.9 . . ?
C7 C8 C9 116.7(11) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 H8 121.6 . . ?
C1 N1 C13 117.0(12) . . ?
C1 N1 C7 121.0(16) . . ?
C13 N1 C7 120.7(16) . . ?
C36A C37A H37A 120.0 . . ?
C36A C37A N5A 120.0 . . ?
N5A C37A H37A 120.0 . . ?
C37A C36A H36A 120.0 . . ?
C35A C36A C37A 120.0 . . ?
C35A C36A H36A 120.0 . . ?
C36A C35A H35A 120.0 . . ?
C34A C35A C36A 120.0 . . ?
C34A C35A H35A 120.0 . . ?
C35A C34A H34A 120.0 . . ?
C35A C34A C33A 120.0 . . ?
C33A C34A H34A 120.0 . . ?
C34A C33A H33A 120.0 . . ?
N5A C33A C34A 120.0 . . ?
N5A C33A H33A 120.0 . . ?
C33A N5A C37A 120.0 . . ?
C35 C36 H36 111.4 . . ?
C37 C36 H36 111.4 . . ?
C37 C36 C35 137(3) . . ?
C36 C35 H35 124.1 . . ?
C36 C35 C34 112(2) . . ?
C34 C35 H35 124.1 . . ?
C35 C34 H34 122.7 . . ?
C33 C34 C35 115(3) . . ?
C33 C34 H34 122.7 . . ?
C34 C33 H33 117.8 . . ?
N5 C33 C34 124(3) . . ?
N5 C33 H33 117.8 . . ?
C36 C37 H37 124.4 . . ?
C36 C37 N5 111(3) . . ?
N5 C37 H37 124.4 . . ?
C37 N5 C33 120(2) . . ?
O3 S1 C32 96.7(12) . . ?
O2 S1 O3 105.7(10) . . ?
O2 S1 C32 111.8(13) . . ?
O1 S1 O3 113.9(12) . . ?
O1 S1 O2 119.4(13) . . ?
O1 S1 C32 107.2(15) . . ?
S1A O1A Bi1 100.5(6) . . ?
O3A S1A C32A 100.7(7) . . ?
O2A S1A C32A 100.7(7) . . ?
O2A S1A O3A 117.1(11) . . ?
O2A S1A O1A 117.5(10) . . ?
O1A S1A C32A 102.9(9) . . ?
O1A S1A O3A 113.9(8) . . ?
S1 O1 Bi1 130.0(13) . . ?
F3 C32 S1 116.7(17) . . ?
F3 C32 F2 109(2) . . ?
F1 C32 S1 118.8(18) . . ?
F1 C32 F3 104.6(19) . . ?
F1 C32 F2 96(2) . . ?
F2 C32 S1 109.9(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 1875341'
loop_
_audit_author_name
_audit_author_address
'Crispin Lichtenberg' 'Julius-Maximilians-Universit?t W?rzburg'
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2019-02-28 downloaded from the CCDC.
;
_audit_creation_date             2016-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H22 Bi F3 N4 O3 S), C5 H5 N'
_chemical_formula_sum            'C55 H49 Bi2 F6 N9 O6 S2'
_chemical_formula_weight         1528.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.7873(9)
_cell_length_b                   19.5468(10)
_cell_length_c                   17.0940(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.1963(13)
_cell_angle_gamma                90
_cell_volume                     5646.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.709
_shelx_estimated_absorpt_T_min   0.124
_exptl_absorpt_coefficient_mu    6.377
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4688
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0914 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.6289.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2968
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            84157
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.771
_diffrn_reflns_theta_min         1.630
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10659
_reflns_number_total             12009
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     736
_refine_ls_number_reflns         12009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0090P)²+8.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0424
_refine_ls_wR_factor_ref         0.0444
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C55A) = Uanis(C54A) = Uanis(C53A) = Uanis(C52A) = Uanis(C51A)
Uanis(N9) = Uanis(N9A)
3. Others
 Sof(C54A)=Sof(H54A)=Sof(C53A)=Sof(H53A)=Sof(C52A)=Sof(H52A)=Sof(C51A)=
 Sof(H51A)=Sof(N9A)=Sof(C55A)=Sof(H55A)=1-FVAR(1)
 Sof(C54)=Sof(H54)=Sof(N9)=Sof(C53)=Sof(H53)=Sof(C55)=Sof(H55)=Sof(C52)=
 Sof(H52)=Sof(C51)=Sof(H51)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C43(H43), C30(H30), C12(H12), C18(H18), C16(H16), C4(H4),
 C17(H17), C15(H15), C24(H24), C48(H48), C23(H23), C46(H46), C8(H8), C32(H32),
 C33(H33), C20(H20), C28(H28), C5(H5), C42(H42), C47(H47), C6(H6), C29(H29),
 C11(H11), C44(H44), C9(H9), C39(H39), C27(H27), C21(H21), C54(H54), C41(H41),
 C45(H45), C40(H40), C36(H36), C10(H10), C35(H35), C34(H34), C53(H53), C55(H55),
  C52(H52), C51(H51), C22(H22), C54A(H54A), C53A(H53A), C52A(H52A), C51A(H51A),
 C55A(H55A)
4.b Fitted hexagon refined as free rotating group:
 C54A(C53A,C52A,C51A,N9A,C55A)
4.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.42313(2) 0.70494(2) 0.97229(2) 0.01227(3) Uani 1 1 d . . . . .
Bi2 Bi 1.12004(2) 0.77458(2) 1.02829(2) 0.01546(3) Uani 1 1 d . . . . .
S2 S 1.19754(4) 0.63142(4) 0.91348(4) 0.01880(15) Uani 1 1 d . . . . .
S1 S 0.33490(5) 0.90515(4) 0.99772(5) 0.02354(16) Uani 1 1 d . . . . .
O6 O 1.24400(12) 0.64091(11) 0.85907(13) 0.0267(5) Uani 1 1 d . . . . .
F5 F 1.21198(12) 0.49862(9) 0.90106(13) 0.0405(5) Uani 1 1 d . . . . .
N1 N 0.55910(13) 0.64728(11) 0.91709(14) 0.0157(5) Uani 1 1 d . . . . .
F4 F 1.11187(13) 0.52918(10) 0.93578(15) 0.0504(6) Uani 1 1 d . . . . .
N7 N 1.14836(13) 0.70602(12) 1.15829(14) 0.0183(5) Uani 1 1 d . . . . .
C19 C 0.49411(17) 0.59618(14) 1.13599(17) 0.0191(6) Uani 1 1 d . . . . .
H19 H 0.4692 0.5632 1.0954 0.023 Uiso 1 1 calc R . . . .
N4 N 0.38654(13) 0.74407(12) 0.82710(14) 0.0165(5) Uani 1 1 d . . . . .
O3 O 0.25768(13) 0.88675(12) 1.00115(14) 0.0325(5) Uani 1 1 d . . . . .
C3 C 0.56336(17) 0.81890(14) 1.00982(17) 0.0184(6) Uani 1 1 d . . . . .
H3 H 0.5308 0.8466 1.0316 0.022 Uiso 1 1 calc R . . . .
C50 C 1.15641(18) 0.54635(15) 0.88913(19) 0.0244(7) Uani 1 1 d . . . . .
N8 N 1.04472(13) 0.84006(12) 0.90487(14) 0.0184(5) Uani 1 1 d . . . . .
C43 C 1.17064(16) 0.73124(15) 1.23493(17) 0.0185(6) Uani 1 1 d . . . . .
H43 H 1.1753 0.7794 1.2424 0.022 Uiso 1 1 calc R . . . .
N3 N 0.49598(13) 0.66130(12) 1.11301(13) 0.0162(5) Uani 1 1 d . . . . .
O5 O 1.24206(16) 0.62625(12) 0.99903(13) 0.0415(6) Uani 1 1 d . . . . .
C31 C 0.93103(16) 0.86235(14) 1.11750(18) 0.0186(6) Uani 1 1 d . . . . .
C1 C 0.58590(16) 0.71297(13) 0.94806(16) 0.0148(6) Uani 1 1 d . . . . .
F3 F 0.32444(15) 1.01352(10) 1.08426(13) 0.0539(6) Uani 1 1 d . . . . .
C30 C 0.88577(16) 0.72868(14) 1.05036(17) 0.0187(6) Uani 1 1 d . . . . .
H30 H 0.8533 0.7517 1.0768 0.022 Uiso 1 1 calc R . . . .
N5 N 0.98352(13) 0.82101(12) 1.08873(14) 0.0168(5) Uani 1 1 d . . . . .
C12 C 0.65956(17) 0.56259(15) 0.9124(2) 0.0245(7) Uani 1 1 d . . . . .
H12 H 0.6750 0.5586 0.9706 0.029 Uiso 1 1 calc R . . . .
N6 N 1.08017(14) 0.90391(12) 1.12939(15) 0.0221(5) Uani 1 1 d . . . . .
C18 C 0.52706(19) 0.57507(15) 1.21647(18) 0.0255(7) Uani 1 1 d . . . . .
H18 H 0.5253 0.5283 1.2310 0.031 Uiso 1 1 calc R . . . .
C16 C 0.56487(18) 0.69044(16) 1.25209(18) 0.0255(7) Uani 1 1 d . . . . .
H16 H 0.5895 0.7244 1.2916 0.031 Uiso 1 1 calc R . . . .
N2 N 0.46914(13) 0.55966(11) 0.90380(14) 0.0163(5) Uani 1 1 d . . . . .
C13 C 0.48870(15) 0.62061(14) 0.92515(15) 0.0138(5) Uani 1 1 d . . . . .
C4 C 0.63640(17) 0.84343(15) 1.00856(17) 0.0217(6) Uani 1 1 d . . . . .
H4 H 0.6540 0.8876 1.0298 0.026 Uiso 1 1 calc R . . . .
C17 C 0.56262(19) 0.62336(16) 1.27544(18) 0.0283(7) Uani 1 1 d . . . . .
H17 H 0.5853 0.6104 1.3315 0.034 Uiso 1 1 calc R . . . .
C38 C 1.15911(18) 0.92973(16) 1.1374(2) 0.0280(7) Uani 1 1 d . . . . .
H38A H 1.1830 0.9018 1.1038 0.042 Uiso 1 1 calc GR . . . .
H38B H 1.1920 0.9274 1.1952 0.042 Uiso 1 1 calc GR . . . .
H38C H 1.1554 0.9773 1.1186 0.042 Uiso 1 1 calc GR . . . .
C15 C 0.53097(17) 0.70761(15) 1.17078(17) 0.0207(6) Uani 1 1 d . . . . .
H15 H 0.5324 0.7540 1.1548 0.025 Uiso 1 1 calc R . . . .
C7 C 0.60059(16) 0.60758(14) 0.87221(18) 0.0177(6) Uani 1 1 d . . . . .
C24 C 0.36325(16) 0.70180(15) 0.76225(17) 0.0191(6) Uani 1 1 d . . . . .
H24 H 0.3637 0.6539 0.7717 0.023 Uiso 1 1 calc R . . . .
C2 C 0.53775(16) 0.75407(14) 0.97939(16) 0.0154(6) Uani 1 1 d . . . . .
C48 C 1.01152(18) 0.80341(15) 0.83649(19) 0.0240(7) Uani 1 1 d . . . . .
H48 H 1.0157 0.7550 0.8396 0.029 Uiso 1 1 calc R . . . .
O4 O 1.12732(13) 0.67359(11) 0.89499(15) 0.0315(5) Uani 1 1 d . . . . .
C23 C 0.33854(17) 0.72570(16) 0.68208(18) 0.0245(7) Uani 1 1 d . . . . .
H23 H 0.3236 0.6947 0.6370 0.029 Uiso 1 1 calc R . . . .
C46 C 0.96503(19) 0.90318(16) 0.7583(2) 0.0310(8) Uani 1 1 d . . . . .
H46 H 0.9380 0.9248 0.7075 0.037 Uiso 1 1 calc R . . . .
C8 C 0.57812(19) 0.61399(16) 0.78728(19) 0.0254(7) Uani 1 1 d . . . . .
H8 H 0.5374 0.6451 0.7597 0.030 Uiso 1 1 calc R . . . .
C32 C 0.87382(18) 0.90111(15) 1.0610(2) 0.0309(8) Uani 1 1 d . . . . .
H32 H 0.8710 0.9010 1.0045 0.037 Uiso 1 1 calc R . . . .
F2 F 0.44270(14) 0.98697(12) 1.09125(15) 0.0616(7) Uani 1 1 d . . . . .
C33 C 0.8218(2) 0.93927(18) 1.0864(3) 0.0503(12) Uani 1 1 d . . . . .
H33 H 0.7830 0.9661 1.0478 0.060 Uiso 1 1 calc R . . . .
F6 F 1.11122(14) 0.54265(10) 0.81136(13) 0.0580(7) Uani 1 1 d . . . . .
C20 C 0.38425(16) 0.81186(15) 0.81368(18) 0.0203(6) Uani 1 1 d . . . . .
H20 H 0.4004 0.8420 0.8595 0.024 Uiso 1 1 calc R . . . .
F1 F 0.38094(17) 0.92833(11) 1.15737(13) 0.0667(8) Uani 1 1 d . . . . .
C28 C 0.90801(18) 0.63207(15) 0.97264(19) 0.0248(7) Uani 1 1 d . . . . .
H28 H 0.8912 0.5894 0.9465 0.030 Uiso 1 1 calc R . . . .
C25 C 0.95723(16) 0.75827(14) 1.04932(16) 0.0161(6) Uani 1 1 d . . . . .
C5 C 0.68315(17) 0.80302(15) 0.97617(17) 0.0212(6) Uani 1 1 d . . . . .
H5 H 0.7325 0.8201 0.9742 0.025 Uiso 1 1 calc R . . . .
C42 C 1.18697(17) 0.68967(16) 1.30314(18) 0.0230(6) Uani 1 1 d . . . . .
H42 H 1.2042 0.7088 1.3569 0.028 Uiso 1 1 calc R . . . .
C37 C 1.05818(16) 0.84730(14) 1.09404(17) 0.0169(6) Uani 1 1 d . . . . .
C47 C 0.97192(18) 0.83288(16) 0.76245(19) 0.0282(7) Uani 1 1 d . . . . .
H47 H 0.9496 0.8055 0.7149 0.034 Uiso 1 1 calc R . . . .
O2 O 0.33571(13) 0.94784(11) 0.92961(13) 0.0327(5) Uani 1 1 d . . . . .
C6 C 0.65911(16) 0.73782(14) 0.94640(16) 0.0179(6) Uani 1 1 d . . . . .
H6 H 0.6922 0.7103 0.9251 0.021 Uiso 1 1 calc R . . . .
C29 C 0.86253(17) 0.66610(15) 1.01299(18) 0.0223(6) Uani 1 1 d . . . . .
H29 H 0.8145 0.6460 1.0150 0.027 Uiso 1 1 calc R . . . .
C11 C 0.6967(2) 0.52289(17) 0.8672(2) 0.0342(8) Uani 1 1 d . . . . .
H11 H 0.7373 0.4916 0.8946 0.041 Uiso 1 1 calc R . . . .
C44 C 1.03731(18) 0.90831(15) 0.90016(19) 0.0229(6) Uani 1 1 d . . . . .
H44 H 1.0604 0.9346 0.9484 0.027 Uiso 1 1 calc R . . . .
C9 C 0.6156(2) 0.57446(18) 0.7426(2) 0.0368(8) Uani 1 1 d . . . . .
H9 H 0.6007 0.5787 0.6844 0.044 Uiso 1 1 calc R . . . .
C39 C 1.14113(17) 0.63757(15) 1.14857(19) 0.0246(7) Uani 1 1 d . . . . .
H39 H 1.1260 0.6192 1.0944 0.030 Uiso 1 1 calc R . . . .
C27 C 0.97861(17) 0.66143(15) 0.97102(18) 0.0219(6) Uani 1 1 d . . . . .
H27 H 1.0100 0.6388 0.9431 0.026 Uiso 1 1 calc R . . . .
C21 C 0.35919(17) 0.83890(16) 0.73549(19) 0.0248(7) Uani 1 1 d . . . . .
H21 H 0.3580 0.8870 0.7277 0.030 Uiso 1 1 calc R . . . .
C14 C 0.39594(16) 0.53239(14) 0.91220(19) 0.0213(6) Uani 1 1 d . . . . .
H14A H 0.3591 0.5222 0.8575 0.032 Uiso 1 1 calc GR . . . .
H14B H 0.3721 0.5663 0.9396 0.032 Uiso 1 1 calc GR . . . .
H14C H 0.4073 0.4904 0.9451 0.032 Uiso 1 1 calc GR . . . .
C54 C 0.7339(8) 0.6449(8) 1.1870(7) 0.059(3) Uani 0.76(3) 1 d . . P A 1
H54 H 0.7102 0.6200 1.1377 0.070 Uiso 0.76(3) 1 calc R . P A 1
C41 C 1.17808(17) 0.61975(16) 1.29254(19) 0.0254(7) Uani 1 1 d . . . . .
H41 H 1.1878 0.5902 1.3388 0.031 Uiso 1 1 calc R . . . .
O1 O 0.39090(14) 0.84961(12) 1.01597(15) 0.0397(6) Uani 1 1 d . . . . .
C45 C 0.99761(18) 0.94194(15) 0.8281(2) 0.0273(7) Uani 1 1 d . . . . .
H45 H 0.9928 0.9904 0.8267 0.033 Uiso 1 1 calc R . . . .
C26 C 1.00392(16) 0.72355(14) 1.00978(17) 0.0178(6) Uani 1 1 d . . . . .
C40 C 1.15490(18) 0.59375(16) 1.2140(2) 0.0278(7) Uani 1 1 d . . . . .
H40 H 1.1485 0.5458 1.2052 0.033 Uiso 1 1 calc R . . . .
N9 N 0.7970(7) 0.6384(6) 1.3291(5) 0.056(2) Uani 0.76(3) 1 d . . P A 1
C36 C 0.9380(2) 0.86330(16) 1.1999(2) 0.0338(8) Uani 1 1 d . . . . .
H36 H 0.9788 0.8387 1.2390 0.041 Uiso 1 1 calc R . . . .
C10 C 0.6742(2) 0.52931(17) 0.7832(2) 0.0368(9) Uani 1 1 d . . . . .
H10 H 0.6995 0.5022 0.7525 0.044 Uiso 1 1 calc R . . . .
C35 C 0.8824(3) 0.9022(2) 1.2242(3) 0.0589(14) Uani 1 1 d . . . . .
H35 H 0.8843 0.9031 1.2803 0.071 Uiso 1 1 calc R . . . .
C34 C 0.8253(2) 0.9390(2) 1.1664(4) 0.0590(14) Uani 1 1 d . . . . .
H34 H 0.7876 0.9646 1.1832 0.071 Uiso 1 1 calc R . . . .
C53 C 0.7378(8) 0.7145(7) 1.1851(6) 0.051(2) Uani 0.76(3) 1 d . . P A 1
H53 H 0.7169 0.7397 1.1355 0.062 Uiso 0.76(3) 1 calc R . P A 1
C49 C 0.3733(2) 0.96083(17) 1.0867(2) 0.0383(9) Uani 1 1 d . . . . .
C55 C 0.7630(9) 0.6122(6) 1.2574(10) 0.060(3) Uani 0.76(3) 1 d . . P A 1
H55 H 0.7584 0.5637 1.2551 0.072 Uiso 0.76(3) 1 calc R . P A 1
C52 C 0.7749(8) 0.7467(5) 1.2610(12) 0.069(4) Uani 0.76(3) 1 d . . P A 1
H52 H 0.7807 0.7951 1.2650 0.083 Uiso 0.76(3) 1 calc R . P A 1
C51 C 0.8025(6) 0.7055(9) 1.3295(6) 0.058(3) Uani 0.76(3) 1 d . . P A 1
H51 H 0.8274 0.7272 1.3808 0.069 Uiso 0.76(3) 1 calc R . P A 1
C22 C 0.33590(17) 0.79566(17) 0.66868(19) 0.0265(7) Uani 1 1 d . . . . .
H22 H 0.3183 0.8135 0.6143 0.032 Uiso 1 1 calc R . . . .
C54A C 0.761(2) 0.6066(9) 1.2557(17) 0.029(6) Uani 0.24(3) 1 d . . P A 2
H54A H 0.7575 0.5581 1.2545 0.035 Uiso 0.24(3) 1 calc R . P A 2
C53A C 0.797(2) 0.6403(12) 1.3293(14) 0.029(6) Uani 0.24(3) 1 d G . P A 2
H53A H 0.8194 0.6148 1.3785 0.035 Uiso 0.24(3) 1 calc R . P A 2
C52A C 0.8021(17) 0.7113(12) 1.3309(13) 0.029(6) Uani 0.24(3) 1 d G . P A 2
H52A H 0.8273 0.7343 1.3813 0.035 Uiso 0.24(3) 1 calc R . P A 2
C51A C 0.7701(18) 0.7486(9) 1.2590(16) 0.029(6) Uani 0.24(3) 1 d G . P A 2
H51A H 0.7733 0.7971 1.2601 0.035 Uiso 0.24(3) 1 calc R . P A 2
N9A N 0.733(2) 0.7149(12) 1.1853(13) 0.056(2) Uani 0.24(3) 1 d G . P A 2
C55A C 0.729(2) 0.6439(12) 1.1837(14) 0.029(6) Uani 0.24(3) 1 d G . P A 2
H55A H 0.7035 0.6208 1.1334 0.035 Uiso 0.24(3) 1 calc R . 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 N4 2.482(2) . ?
Bi1 N3 2.499(2) . ?
Bi1 C13 2.305(3) . ?
Bi1 C2 2.222(3) . ?
Bi1 O1 3.025(2) . ?
Bi2 N7 2.508(2) . ?
Bi2 N8 2.474(2) . ?
Bi2 O4 3.048(2) . ?
Bi2 C37 2.295(3) . ?
Bi2 C26 2.225(3) . ?
S2 O6 1.436(2) . ?
S2 C50 1.812(3) . ?
S2 O5 1.433(2) . ?
S2 O4 1.447(2) . ?
S1 O3 1.439(2) . ?
S1 O2 1.436(2) . ?
S1 O1 1.440(2) . ?
S1 C49 1.820(3) . ?
F5 C50 1.328(3) . ?
N1 C1 1.414(3) . ?
N1 C13 1.402(3) . ?
N1 C7 1.445(3) . ?
F4 C50 1.331(4) . ?
N7 C43 1.339(4) . ?
N7 C39 1.349(4) . ?
C19 N3 1.336(4) . ?
C19 C18 1.379(4) . ?
N4 C24 1.340(4) . ?
N4 C20 1.343(4) . ?
C3 C4 1.391(4) . ?
C3 C2 1.391(4) . ?
C50 F6 1.323(3) . ?
N8 C48 1.341(4) . ?
N8 C44 1.340(4) . ?
C43 C42 1.376(4) . ?
N3 C15 1.341(4) . ?
C31 N5 1.433(3) . ?
C31 C32 1.389(4) . ?
C31 C36 1.374(4) . ?
C1 C2 1.397(4) . ?
C1 C6 1.399(4) . ?
F3 C49 1.340(4) . ?
C30 C25 1.402(4) . ?
C30 C29 1.382(4) . ?
N5 C25 1.407(3) . ?
N5 C37 1.400(3) . ?
C12 C7 1.377(4) . ?
C12 C11 1.397(4) . ?
N6 C38 1.458(4) . ?
N6 C37 1.263(4) . ?
C18 C17 1.382(4) . ?
C16 C17 1.375(4) . ?
C16 C15 1.373(4) . ?
N2 C13 1.263(3) . ?
N2 C14 1.455(3) . ?
C4 C5 1.382(4) . ?
C7 C8 1.386(4) . ?
C24 C23 1.383(4) . ?
C48 C47 1.369(4) . ?
C23 C22 1.385(4) . ?
C46 C47 1.379(4) . ?
C46 C45 1.380(4) . ?
C8 C9 1.394(4) . ?
C32 C33 1.361(5) . ?
F2 C49 1.316(4) . ?
C33 C34 1.350(6) . ?
C20 C21 1.376(4) . ?
F1 C49 1.334(4) . ?
C28 C29 1.386(4) . ?
C28 C27 1.389(4) . ?
C25 C26 1.399(4) . ?
C5 C6 1.389(4) . ?
C42 C41 1.381(4) . ?
C11 C10 1.372(5) . ?
C44 C45 1.380(4) . ?
C9 C10 1.377(5) . ?
C39 C40 1.369(4) . ?
C27 C26 1.389(4) . ?
C21 C22 1.376(4) . ?
C54 C53 1.363(9) . ?
C54 C55 1.317(9) . ?
C41 C40 1.373(4) . ?
N9 C55 1.291(11) . ?
N9 C51 1.317(11) . ?
C36 C35 1.410(5) . ?
C35 C34 1.377(7) . ?
C53 C52 1.409(11) . ?
C52 C51 1.378(10) . ?
C54A C53A 1.3900 . ?
C54A C55A 1.3900 . ?
C53A C52A 1.3900 . ?
C52A C51A 1.3900 . ?
C51A N9A 1.3900 . ?
N9A C55A 1.3900 . ?

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
N4 Bi1 N3 164.35(7) . . ?
N4 Bi1 O1 87.02(7) . . ?
N3 Bi1 O1 99.36(7) . . ?
C13 Bi1 N4 82.77(8) . . ?
C13 Bi1 N3 85.73(8) . . ?
C13 Bi1 O1 155.56(8) . . ?
C2 Bi1 N4 82.59(8) . . ?
C2 Bi1 N3 84.48(8) . . ?
C2 Bi1 C13 76.84(10) . . ?
C2 Bi1 O1 79.86(9) . . ?
N7 Bi2 O4 105.83(7) . . ?
N8 Bi2 N7 159.67(8) . . ?
N8 Bi2 O4 80.54(7) . . ?
C37 Bi2 N7 83.77(9) . . ?
C37 Bi2 N8 83.24(9) . . ?
C37 Bi2 O4 154.97(8) . . ?
C26 Bi2 N7 78.88(9) . . ?
C26 Bi2 N8 83.07(9) . . ?
C26 Bi2 O4 81.82(8) . . ?
C26 Bi2 C37 77.39(10) . . ?
O6 S2 C50 104.03(14) . . ?
O6 S2 O4 114.65(13) . . ?
O5 S2 O6 115.07(15) . . ?
O5 S2 C50 102.98(14) . . ?
O5 S2 O4 115.31(15) . . ?
O4 S2 C50 102.33(14) . . ?
O3 S1 O1 114.03(15) . . ?
O3 S1 C49 103.25(16) . . ?
O2 S1 O3 115.45(14) . . ?
O2 S1 O1 115.61(15) . . ?
O2 S1 C49 103.52(15) . . ?
O1 S1 C49 102.48(16) . . ?
C1 N1 C7 121.2(2) . . ?
C13 N1 C1 120.5(2) . . ?
C13 N1 C7 118.2(2) . . ?
C43 N7 Bi2 125.91(18) . . ?
C43 N7 C39 118.3(3) . . ?
C39 N7 Bi2 115.83(19) . . ?
N3 C19 C18 122.5(3) . . ?
C24 N4 Bi1 123.63(18) . . ?
C24 N4 C20 118.8(2) . . ?
C20 N4 Bi1 117.34(18) . . ?
C4 C3 C2 120.4(3) . . ?
F5 C50 S2 112.4(2) . . ?
F5 C50 F4 106.5(2) . . ?
F4 C50 S2 111.5(2) . . ?
F6 C50 S2 110.8(2) . . ?
F6 C50 F5 107.8(3) . . ?
F6 C50 F4 107.4(3) . . ?
C48 N8 Bi2 116.16(18) . . ?
C44 N8 Bi2 125.67(19) . . ?
C44 N8 C48 118.1(3) . . ?
N7 C43 C42 122.1(3) . . ?
C19 N3 Bi1 123.73(18) . . ?
C19 N3 C15 118.4(2) . . ?
C15 N3 Bi1 117.41(18) . . ?
C32 C31 N5 118.9(3) . . ?
C36 C31 N5 119.9(3) . . ?
C36 C31 C32 121.2(3) . . ?
C2 C1 N1 119.4(2) . . ?
C2 C1 C6 119.6(3) . . ?
C6 C1 N1 121.0(2) . . ?
C29 C30 C25 120.0(3) . . ?
C25 N5 C31 120.1(2) . . ?
C37 N5 C31 118.5(2) . . ?
C37 N5 C25 121.2(2) . . ?
C7 C12 C11 119.8(3) . . ?
C37 N6 C38 119.6(3) . . ?
C19 C18 C17 118.6(3) . . ?
C15 C16 C17 118.9(3) . . ?
C13 N2 C14 119.4(2) . . ?
N1 C13 Bi1 109.47(17) . . ?
N2 C13 Bi1 130.7(2) . . ?
N2 C13 N1 119.8(2) . . ?
C5 C4 C3 119.4(3) . . ?
C16 C17 C18 119.2(3) . . ?
N3 C15 C16 122.5(3) . . ?
C12 C7 N1 120.9(3) . . ?
C12 C7 C8 120.4(3) . . ?
C8 C7 N1 118.7(3) . . ?
N4 C24 C23 122.1(3) . . ?
C3 C2 Bi1 127.0(2) . . ?
C3 C2 C1 119.9(2) . . ?
C1 C2 Bi1 113.10(19) . . ?
N8 C48 C47 122.7(3) . . ?
S2 O4 Bi2 116.17(12) . . ?
C24 C23 C22 118.8(3) . . ?
C47 C46 C45 119.7(3) . . ?
C7 C8 C9 119.5(3) . . ?
C33 C32 C31 120.0(4) . . ?
C34 C33 C32 120.1(4) . . ?
N4 C20 C21 121.9(3) . . ?
C29 C28 C27 118.9(3) . . ?
C30 C25 N5 121.4(2) . . ?
C26 C25 C30 118.9(3) . . ?
C26 C25 N5 119.7(2) . . ?
C4 C5 C6 121.1(3) . . ?
C43 C42 C41 119.2(3) . . ?
N5 C37 Bi2 109.32(18) . . ?
N6 C37 Bi2 130.7(2) . . ?
N6 C37 N5 119.9(3) . . ?
C48 C47 C46 118.6(3) . . ?
C5 C6 C1 119.6(3) . . ?
C30 C29 C28 121.2(3) . . ?
C10 C11 C12 119.7(3) . . ?
N8 C44 C45 122.8(3) . . ?
C10 C9 C8 119.7(3) . . ?
N7 C39 C40 122.3(3) . . ?
C28 C27 C26 120.8(3) . . ?
C20 C21 C22 119.5(3) . . ?
C55 C54 C53 119.9(6) . . ?
C40 C41 C42 118.8(3) . . ?
S1 O1 Bi1 145.36(14) . . ?
C46 C45 C44 118.1(3) . . ?
C25 C26 Bi2 112.24(19) . . ?
C27 C26 Bi2 127.4(2) . . ?
C27 C26 C25 120.1(3) . . ?
C39 C40 C41 119.3(3) . . ?
C55 N9 C51 114.3(6) . . ?
C31 C36 C35 117.5(4) . . ?
C11 C10 C9 120.9(3) . . ?
C34 C35 C36 119.9(4) . . ?
C33 C34 C35 121.2(4) . . ?
C54 C53 C52 115.9(7) . . ?
F3 C49 S1 111.3(2) . . ?
F2 C49 S1 112.5(3) . . ?
F2 C49 F3 106.9(3) . . ?
F2 C49 F1 107.6(3) . . ?
F1 C49 S1 112.2(2) . . ?
F1 C49 F3 106.0(3) . . ?
N9 C55 C54 127.5(8) . . ?
C51 C52 C53 117.4(6) . . ?
N9 C51 C52 124.9(7) . . ?
C21 C22 C23 118.9(3) . . ?
C53A C54A C55A 120.0 . . ?
C52A C53A C54A 120.0 . . ?
C53A C52A C51A 120.0 . . ?
N9A C51A C52A 120.0 . . ?
C55A N9A C51A 120.0 . . ?
N9A C55A C54A 120.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 1875342'
loop_
_audit_author_name
_audit_author_address
'Crispin Lichtenberg' 'Julius-Maximilians-Universit?t W?rzburg'
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2019-02-28 downloaded from the CCDC.
;
_audit_creation_date             2016-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C28 H28 Bi F3 N4 O3 S, 0.51(C5 H5 N), 0.49(C4 H10 O)'
_chemical_formula_sum            'C32.51 H35.44 Bi F3 N4.51 O3.49 S'
_chemical_formula_weight         843.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.527(3)
_cell_length_b                   27.102(11)
_cell_length_c                   11.870(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.991(15)
_cell_angle_gamma                90
_cell_volume                     3384(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9632
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.700
_exptl_absorpt_coefficient_mu    5.328
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0838 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.7931.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.072
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            62337
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.190
_diffrn_reflns_theta_max         25.190
_diffrn_reflns_theta_min         1.874
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5180
_reflns_number_total             6040
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6040
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+3.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0518
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-C36
 1.5 with sigma of 0.02
 C36-C37
 1.54 with sigma of 0.04
 C34-C35
 1.54 with sigma of 0.04
 C35-O4
 1.5 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C37, C36, O4, C35, C34
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C30, C29, N5, C33, C32, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(O4)=
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=1-FVAR(1)
 Sof(C30)=Sof(H30)=Sof(C29)=Sof(H29)=Sof(N5)=Sof(C33)=Sof(H33)=Sof(C32)=
 Sof(H32)=Sof(C31)=Sof(H31)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B)
5.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C3(H3), C8(H8), C23(H23), C5(H5), C27(H27), C22(H22), C21(H21),
 C6(H6), C24(H24), C9(H9), C20(H20), C4(H4), C12(H12), C10(H10), C11(H11),
 C26(H26), C19(H19), C25(H25), C30(H30), C29(H29), C33(H33), C32(H32), C31(H31)
5.c Fitted hexagon refined as free rotating group:
 C30(C29,N5,C33,C32,C31)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C37(H37A,H37B,
 H37C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.69932(2) 0.59889(2) 0.92960(2) 0.01429(5) Uani 1 1 d . . . . .
S1 S 0.51620(8) 0.51990(3) 1.18163(7) 0.01892(18) Uani 1 1 d . . . . .
O2 O 0.5605(2) 0.47077(9) 1.1574(2) 0.0281(6) Uani 1 1 d . . . . .
N1 N 0.8387(3) 0.69675(10) 0.8861(2) 0.0186(6) Uani 1 1 d . . . . .
F1 F 0.4725(3) 0.48798(9) 1.38486(18) 0.0528(7) Uani 1 1 d . . . . .
O3 O 0.3831(2) 0.52809(10) 1.1617(2) 0.0342(6) Uani 1 1 d . . . . .
N3 N 0.5136(3) 0.65316(10) 0.9608(2) 0.0189(6) Uani 1 1 d . . . . .
C18 C 0.5171(4) 0.70264(13) 0.9603(3) 0.0292(8) Uani 1 1 d . . . . .
H18 H 0.5937 0.7186 0.9410 0.035 Uiso 1 1 calc R . . . .
C2 C 0.8092(3) 0.64575(12) 1.0522(3) 0.0171(7) Uani 1 1 d . . . . .
N2 N 0.7671(3) 0.67011(10) 0.7115(2) 0.0237(7) Uani 1 1 d . . . . .
N4 N 0.9093(3) 0.55843(10) 0.8905(2) 0.0211(6) Uani 1 1 d . . . . .
C13 C 0.7740(3) 0.66202(11) 0.8161(3) 0.0176(7) Uani 1 1 d . . . . .
C1 C 0.8618(3) 0.68764(12) 1.0025(3) 0.0171(7) Uani 1 1 d . . . . .
C3 C 0.8326(3) 0.63647(12) 1.1658(3) 0.0200(7) Uani 1 1 d . . . . .
H3 H 0.7959 0.6083 1.1995 0.024 Uiso 1 1 calc R . . . .
C8 C 1.0205(4) 0.73670(13) 0.8012(3) 0.0242(8) Uani 1 1 d . . . . .
H8 H 1.0647 0.7061 0.8046 0.029 Uiso 1 1 calc R . . . .
C7 C 0.8975(3) 0.73964(12) 0.8368(3) 0.0207(8) Uani 1 1 d . . . . .
C23 C 1.0224(3) 0.58053(14) 0.8855(3) 0.0267(8) Uani 1 1 d . . . . .
H23 H 1.0275 0.6151 0.8987 0.032 Uiso 1 1 calc R . . . .
O1 O 0.5975(2) 0.55917(8) 1.14415(19) 0.0227(5) Uani 1 1 d . . . . .
F3 F 0.4955(2) 0.56640(8) 1.37453(18) 0.0406(6) Uani 1 1 d . . . . .
F2 F 0.6576(2) 0.51955(10) 1.36718(19) 0.0491(7) Uani 1 1 d . . . . .
C5 C 0.9603(3) 0.70939(14) 1.1819(3) 0.0249(8) Uani 1 1 d . . . . .
H5 H 1.0126 0.7310 1.2262 0.030 Uiso 1 1 calc R . . . .
C27 C 0.9025(3) 0.50985(13) 0.8704(3) 0.0258(8) Uani 1 1 d . . . . .
H27 H 0.8223 0.4939 0.8731 0.031 Uiso 1 1 calc R . . . .
C22 C 0.4061(3) 0.63085(13) 0.9894(3) 0.0230(8) Uani 1 1 d . . . . .
H22 H 0.4033 0.5958 0.9906 0.028 Uiso 1 1 calc R . . . .
C16 C 0.5604(4) 0.63324(14) 0.6497(3) 0.0312(9) Uani 1 1 d . . . . .
H16A H 0.5454 0.6155 0.7200 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.5176 0.6160 0.5866 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.5267 0.6668 0.6549 0.047 Uiso 1 1 calc GR . . . .
C21 C 0.2986(3) 0.65707(14) 1.0171(3) 0.0302(9) Uani 1 1 d . . . . .
H21 H 0.2232 0.6404 1.0367 0.036 Uiso 1 1 calc R . . . .
C6 C 0.9364(3) 0.71989(12) 1.0688(3) 0.0214(8) Uani 1 1 d . . . . .
H6 H 0.9704 0.7489 1.0365 0.026 Uiso 1 1 calc R . . . .
C24 C 1.1314(4) 0.55537(14) 0.8622(3) 0.0322(9) Uani 1 1 d . . . . .
H24 H 1.2104 0.5722 0.8593 0.039 Uiso 1 1 calc R . . . .
C9 C 1.0801(4) 0.77877(14) 0.7599(3) 0.0317(9) Uani 1 1 d . . . . .
H9 H 1.1646 0.7769 0.7349 0.038 Uiso 1 1 calc R . . . .
C14 C 0.7029(4) 0.63541(13) 0.6307(3) 0.0255(8) Uani 1 1 d . . . . .
C20 C 0.3035(4) 0.70832(15) 1.0158(4) 0.0361(10) Uani 1 1 d . . . . .
H20 H 0.2315 0.7273 1.0348 0.043 Uiso 1 1 calc R . . . .
C4 C 0.9093(4) 0.66793(13) 1.2313(3) 0.0264(8) Uani 1 1 d . . . . .
H4 H 0.9264 0.6610 1.3088 0.032 Uiso 1 1 calc R . . . .
C12 C 0.8318(4) 0.78379(13) 0.8317(3) 0.0266(8) Uani 1 1 d . . . . .
H12 H 0.7466 0.7856 0.8553 0.032 Uiso 1 1 calc R . . . .
C10 C 1.0153(4) 0.82295(14) 0.7559(3) 0.0305(9) Uani 1 1 d . . . . .
H10 H 1.0559 0.8516 0.7285 0.037 Uiso 1 1 calc R . . . .
C17 C 0.7626(4) 0.58406(14) 0.6362(3) 0.0294(9) Uani 1 1 d . . . . .
H17A H 0.8552 0.5870 0.6331 0.044 Uiso 1 1 calc GR . . . .
H17B H 0.7304 0.5643 0.5722 0.044 Uiso 1 1 calc GR . . . .
H17C H 0.7407 0.5680 0.7068 0.044 Uiso 1 1 calc GR . . . .
C11 C 0.8926(4) 0.82593(14) 0.7912(3) 0.0325(9) Uani 1 1 d . . . . .
H11 H 0.8489 0.8566 0.7881 0.039 Uiso 1 1 calc R . . . .
C28 C 0.5358(4) 0.52381(13) 1.3350(3) 0.0270(8) Uani 1 1 d . . . . .
C26 C 1.0081(4) 0.48223(14) 0.8461(3) 0.0332(9) Uani 1 1 d . . . . .
H26 H 1.0005 0.4479 0.8317 0.040 Uiso 1 1 calc R . . . .
C19 C 0.4149(4) 0.73122(15) 0.9865(4) 0.0401(11) Uani 1 1 d . . . . .
H19 H 0.4205 0.7662 0.9846 0.048 Uiso 1 1 calc R . . . .
C25 C 1.1243(4) 0.50501(15) 0.8428(4) 0.0365(10) Uani 1 1 d . . . . .
H25 H 1.1986 0.4866 0.8276 0.044 Uiso 1 1 calc R . . . .
C15 C 0.7241(5) 0.65665(16) 0.5137(3) 0.0464(12) Uani 1 1 d . . . . .
H15A H 0.6850 0.6894 0.5077 0.070 Uiso 1 1 calc GR . . . .
H15B H 0.6854 0.6348 0.4564 0.070 Uiso 1 1 calc GR . . . .
H15C H 0.8155 0.6594 0.5020 0.070 Uiso 1 1 calc GR . . . .
C30 C 1.1909(9) 0.5752(2) 0.5113(7) 0.080(4) Uani 0.512(7) 1 d . U P A 1
H30 H 1.2078 0.5422 0.4898 0.096 Uiso 0.512(7) 1 calc R . P A 1
C29 C 1.1081(8) 0.6041(3) 0.4457(6) 0.111(8) Uani 0.512(7) 1 d G U P A 1
H29 H 1.0684 0.5908 0.3794 0.133 Uiso 0.512(7) 1 calc R . P A 1
N5 N 1.0834(7) 0.6525(2) 0.4772(5) 0.046(2) Uani 0.512(7) 1 d G U P A 1
C33 C 1.1415(8) 0.6719(2) 0.5743(6) 0.068(4) Uani 0.512(7) 1 d G U P A 1
H33 H 1.1246 0.7050 0.5958 0.082 Uiso 0.512(7) 1 calc R . P A 1
C32 C 1.2243(8) 0.6431(3) 0.6399(5) 0.059(3) Uani 0.512(7) 1 d G U P A 1
H32 H 1.2640 0.6564 0.7062 0.071 Uiso 0.512(7) 1 calc R . P A 1
C31 C 1.2490(7) 0.5947(3) 0.6084(6) 0.066(3) Uani 0.512(7) 1 d G U P A 1
H31 H 1.3056 0.5750 0.6533 0.079 Uiso 0.512(7) 1 calc R . P A 1
C35 C 1.1363(17) 0.5701(7) 0.4035(14) 0.119(6) Uani 0.488(7) 1 d D U P A 2
H35A H 1.1230 0.5746 0.3211 0.143 Uiso 0.488(7) 1 calc R . P A 2
H35B H 1.2224 0.5563 0.4176 0.143 Uiso 0.488(7) 1 calc R . P A 2
C37 C 1.2176(14) 0.6665(5) 0.6173(13) 0.078(4) Uani 0.488(7) 1 d D U P A 2
H37A H 1.2347 0.6613 0.6981 0.117 Uiso 0.488(7) 1 calc GR . P A 2
H37B H 1.1798 0.6992 0.6053 0.117 Uiso 0.488(7) 1 calc GR . P A 2
H37C H 1.2973 0.6643 0.5773 0.117 Uiso 0.488(7) 1 calc GR . P A 2
O4 O 1.1266(13) 0.6200(5) 0.4623(9) 0.107(5) Uani 0.488(7) 1 d D U P A 2
C36 C 1.139(3) 0.6329(9) 0.5791(14) 0.198(11) Uani 0.488(7) 1 d D U P A 2
H36A H 1.0534 0.6428 0.6025 0.237 Uiso 0.488(7) 1 calc R . P A 2
H36B H 1.1606 0.6021 0.6204 0.237 Uiso 0.488(7) 1 calc R . P A 2
C34 C 1.0480(16) 0.5382(6) 0.4419(13) 0.113(6) Uani 0.488(7) 1 d D U P A 2
H34A H 1.0673 0.5307 0.5215 0.170 Uiso 0.488(7) 1 calc GR . P A 2
H34B H 1.0495 0.5077 0.3978 0.170 Uiso 0.488(7) 1 calc GR . P A 2
H34C H 0.9635 0.5533 0.4343 0.170 Uiso 0.488(7) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N3 2.485(3) . ?
Bi1 C2 2.225(3) . ?
Bi1 N4 2.525(3) . ?
Bi1 C13 2.331(3) . ?
Bi1 O1 2.997(2) . ?
S1 O2 1.443(3) . ?
S1 O3 1.430(3) . ?
S1 O1 1.446(2) . ?
S1 C28 1.828(4) . ?
N1 C13 1.415(4) . ?
N1 C1 1.416(4) . ?
N1 C7 1.450(4) . ?
F1 C28 1.329(4) . ?
N3 C18 1.341(4) . ?
N3 C22 1.337(4) . ?
C18 C19 1.371(5) . ?
C2 C1 1.402(5) . ?
C2 C3 1.386(5) . ?
N2 C13 1.261(4) . ?
N2 C14 1.489(4) . ?
N4 C23 1.335(5) . ?
N4 C27 1.339(5) . ?
C1 C6 1.399(5) . ?
C3 C4 1.392(5) . ?
C8 C7 1.378(5) . ?
C8 C9 1.398(5) . ?
C7 C12 1.382(5) . ?
C23 C24 1.371(5) . ?
F3 C28 1.322(4) . ?
F2 C28 1.330(4) . ?
C5 C6 1.386(5) . ?
C5 C4 1.384(5) . ?
C27 C26 1.379(5) . ?
C22 C21 1.385(5) . ?
C16 C14 1.525(5) . ?
C21 C20 1.390(6) . ?
C24 C25 1.386(6) . ?
C9 C10 1.378(5) . ?
C14 C17 1.528(5) . ?
C14 C15 1.526(5) . ?
C20 C19 1.381(6) . ?
C12 C11 1.403(5) . ?
C10 C11 1.374(6) . ?
C26 C25 1.372(5) . ?
C30 C29 1.3900 . ?
C30 C31 1.3900 . ?
C29 N5 1.3900 . ?
N5 C33 1.3900 . ?
C33 C32 1.3900 . ?
C32 C31 1.3900 . ?
C35 O4 1.525(15) . ?
C35 C34 1.360(18) . ?
C37 C36 1.301(19) . ?
O4 C36 1.432(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
N3 Bi1 N4 169.39(9) . . ?
N3 Bi1 O1 77.27(8) . . ?
C2 Bi1 N3 87.63(11) . . ?
C2 Bi1 N4 85.97(11) . . ?
C2 Bi1 C13 77.35(12) . . ?
C2 Bi1 O1 80.94(10) . . ?
N4 Bi1 O1 109.97(8) . . ?
C13 Bi1 N3 86.24(10) . . ?
C13 Bi1 N4 84.12(10) . . ?
C13 Bi1 O1 153.18(9) . . ?
O2 S1 O1 114.78(15) . . ?
O2 S1 C28 103.05(16) . . ?
O3 S1 O2 115.57(16) . . ?
O3 S1 O1 114.98(16) . . ?
O3 S1 C28 103.39(17) . . ?
O1 S1 C28 102.49(15) . . ?
C13 N1 C1 121.3(3) . . ?
C13 N1 C7 120.0(3) . . ?
C1 N1 C7 118.2(3) . . ?
C18 N3 Bi1 124.7(2) . . ?
C22 N3 Bi1 116.6(2) . . ?
C22 N3 C18 118.5(3) . . ?
N3 C18 C19 122.8(4) . . ?
C1 C2 Bi1 113.0(2) . . ?
C3 C2 Bi1 127.2(2) . . ?
C3 C2 C1 119.8(3) . . ?
C13 N2 C14 122.3(3) . . ?
C23 N4 Bi1 126.9(2) . . ?
C23 N4 C27 118.4(3) . . ?
C27 N4 Bi1 114.7(2) . . ?
N1 C13 Bi1 108.3(2) . . ?
N2 C13 Bi1 133.5(2) . . ?
N2 C13 N1 118.2(3) . . ?
C2 C1 N1 119.6(3) . . ?
C6 C1 N1 121.0(3) . . ?
C6 C1 C2 119.4(3) . . ?
C2 C3 C4 120.8(3) . . ?
C7 C8 C9 119.9(3) . . ?
C8 C7 N1 119.8(3) . . ?
C8 C7 C12 120.7(3) . . ?
C12 C7 N1 119.5(3) . . ?
N4 C23 C24 122.6(3) . . ?
S1 O1 Bi1 139.38(13) . . ?
C4 C5 C6 121.1(3) . . ?
N4 C27 C26 122.2(3) . . ?
N3 C22 C21 122.2(3) . . ?
C22 C21 C20 118.6(4) . . ?
C5 C6 C1 119.8(3) . . ?
C23 C24 C25 118.9(4) . . ?
C10 C9 C8 119.6(4) . . ?
N2 C14 C16 110.8(3) . . ?
N2 C14 C17 111.7(3) . . ?
N2 C14 C15 105.7(3) . . ?
C16 C14 C17 111.4(3) . . ?
C16 C14 C15 109.0(3) . . ?
C15 C14 C17 108.0(3) . . ?
C19 C20 C21 118.9(4) . . ?
C5 C4 C3 119.1(3) . . ?
C7 C12 C11 119.1(4) . . ?
C11 C10 C9 120.6(3) . . ?
C10 C11 C12 120.1(4) . . ?
F1 C28 S1 111.1(2) . . ?
F1 C28 F2 107.6(3) . . ?
F3 C28 S1 112.2(3) . . ?
F3 C28 F1 107.9(3) . . ?
F3 C28 F2 107.0(3) . . ?
F2 C28 S1 110.8(3) . . ?
C25 C26 C27 119.2(4) . . ?
C18 C19 C20 118.9(4) . . ?
C26 C25 C24 118.8(4) . . ?
C29 C30 C31 120.0 . . ?
C30 C29 N5 120.0 . . ?
C33 N5 C29 120.0 . . ?
C32 C33 N5 120.0 . . ?
C33 C32 C31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C34 C35 O4 110.6(14) . . ?
C36 O4 C35 130.9(15) . . ?
C37 C36 O4 123.0(18) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
