# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1520801'
_audit_update_record             
;
2017-02-21 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 Bi F3 N O3 S'
_chemical_formula_sum            'C22 H19 Bi F3 N O3 S'
_chemical_formula_weight         643.42

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.8797(6)
_cell_length_b                   10.1848(4)
_cell_length_c                   10.9733(5)
_cell_angle_alpha                78.190(4)
_cell_angle_beta                 86.738(4)
_cell_angle_gamma                83.332(4)
_cell_volume                     1072.86(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    110
_cell_measurement_reflns_used    4802
_cell_measurement_theta_min      3.0430
_cell_measurement_theta_max      27.7910

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    8.364
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.57126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6582
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.063
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3738
_reflns_number_gt                3482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;Brandenburg, K. [or Brandenburg, K. & Putz, H., or Brandenburg, K. & Berndt,
 M.] (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
; Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).
 J. Appl. Cryst. 37, 335-338.
;
_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0120P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0516
_refine_ls_wR_factor_gt          0.0503
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3639(5) 0.1540(4) 0.1089(4) 0.0132(10) Uani 1 1 d . . . . .
C2 C 0.3195(5) 0.0890(4) 0.0225(4) 0.0190(11) Uani 1 1 d . . . . .
H2 H 0.3470 -0.0023 0.0269 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2339(5) 0.1587(5) -0.0711(4) 0.0214(12) Uani 1 1 d . . . . .
H3 H 0.2015 0.1139 -0.1275 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1979(5) 0.2944(4) -0.0792(4) 0.0227(12) Uani 1 1 d . . . . .
H4 H 0.1429 0.3421 -0.1430 0.027 Uiso 1 1 calc R U . . .
C5 C 0.2420(5) 0.3610(4) 0.0060(4) 0.0165(11) Uani 1 1 d . . . . .
H5 H 0.2154 0.4526 0.0003 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3265(5) 0.2912(4) 0.1008(4) 0.0127(10) Uani 1 1 d . . . . .
C7 C 0.3680(5) 0.3608(4) 0.1998(4) 0.0173(11) Uani 1 1 d . . . . .
H7A H 0.3761 0.4549 0.1637 0.021 Uiso 1 1 calc R U . . .
H7B H 0.2978 0.3572 0.2655 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5013(5) 0.3002(4) 0.3889(4) 0.0157(11) Uani 1 1 d . . . . .
H8A H 0.4847 0.3928 0.3999 0.019 Uiso 1 1 calc R U . . .
H8B H 0.5893 0.2622 0.4223 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3914(5) 0.2201(4) 0.4563(4) 0.0124(10) Uani 1 1 d . . . . .
C10 C 0.3068(6) 0.2649(5) 0.5487(4) 0.0182(12) Uani 1 1 d . . . . .
H10 H 0.3219 0.3433 0.5745 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2011(5) 0.1938(5) 0.6021(4) 0.0195(12) Uani 1 1 d . . . . .
H11 H 0.1446 0.2250 0.6631 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1781(5) 0.0759(5) 0.5656(4) 0.0193(11) Uani 1 1 d . . . . .
H12 H 0.1066 0.0280 0.6020 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2624(5) 0.0302(4) 0.4744(4) 0.0177(11) Uani 1 1 d . . . . .
H13 H 0.2485 -0.0498 0.4507 0.021 Uiso 1 1 calc R U . . .
C14 C 0.3659(5) 0.1020(4) 0.4189(4) 0.0126(10) Uani 1 1 d . . . . .
C15 C 0.6124(5) 0.3660(4) 0.1803(4) 0.0152(11) Uani 1 1 d . . . . .
H15A H 0.6083 0.4558 0.1982 0.018 Uiso 1 1 calc R U . . .
H15B H 0.5954 0.3762 0.0925 0.018 Uiso 1 1 calc R U . . .
C16 C 0.7535(5) 0.2977(4) 0.2034(4) 0.0179(11) Uani 1 1 d . . . . .
C17 C 0.8104(5) 0.2090(4) 0.1294(4) 0.0195(11) Uani 1 1 d . . . . .
H17 H 0.7595 0.1904 0.0675 0.023 Uiso 1 1 calc R U . . .
C18 C 0.9420(6) 0.1480(5) 0.1468(5) 0.0236(12) Uani 1 1 d . . . . .
H18 H 0.9787 0.0882 0.0970 0.028 Uiso 1 1 calc R U . . .
C19 C 1.0191(6) 0.1749(5) 0.2370(5) 0.0274(13) Uani 1 1 d . . . . .
H19 H 1.1078 0.1336 0.2482 0.033 Uiso 1 1 calc R U . . .
C20 C 0.9639(6) 0.2640(5) 0.3112(5) 0.0309(14) Uani 1 1 d . . . . .
H20 H 1.0156 0.2826 0.3727 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8334(6) 0.3247(5) 0.2941(5) 0.0247(12) Uani 1 1 d . . . . .
H21 H 0.7975 0.3850 0.3438 0.030 Uiso 1 1 calc R U . . .
C22 C 0.1793(6) -0.2768(5) 0.2719(5) 0.0260(13) Uani 1 1 d . . . . .
N1 N 0.5008(4) 0.2958(3) 0.2538(3) 0.0126(9) Uani 1 1 d . . . . .
O1 O 0.3742(4) -0.1374(3) 0.2766(3) 0.0223(8) Uani 1 1 d . . . . .
O2 O 0.4184(4) -0.3791(3) 0.3424(3) 0.0291(10) Uani 1 1 d . . . . .
O3 O 0.3902(4) -0.2807(3) 0.1231(3) 0.0282(9) Uani 1 1 d . . . . .
F1 F 0.1385(4) -0.2680(3) 0.3877(3) 0.0434(9) Uani 1 1 d . . . . .
F2 F 0.1110(3) -0.1766(3) 0.1962(3) 0.0424(9) Uani 1 1 d . . . . .
F3 F 0.1436(4) -0.3913(3) 0.2504(3) 0.0437(9) Uani 1 1 d . . . . .
S1 S 0.36227(14) -0.27010(11) 0.24994(11) 0.0166(3) Uani 1 1 d . . . . .
Bi1 Bi 0.50581(2) 0.05837(2) 0.25896(2) 0.01267(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(6) . ?
C1 C6 1.390(6) . ?
C1 Bi1 2.217(4) . ?
C2 C3 1.392(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(6) . ?
C7 N1 1.496(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.492(5) . ?
C8 C9 1.502(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.393(6) . ?
C9 C14 1.401(6) . ?
C10 C11 1.375(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(7) . ?
C13 H13 0.9300 . ?
C14 Bi1 2.256(5) . ?
C15 N1 1.491(6) . ?
C15 C16 1.495(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.387(6) . ?
C16 C21 1.393(7) . ?
C17 C18 1.380(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 F2 1.321(5) . ?
C22 F3 1.325(5) . ?
C22 F1 1.329(6) . ?
C22 S1 1.817(6) . ?
N1 Bi1 2.402(3) . ?
O1 S1 1.460(3) . ?
O1 Bi1 2.474(3) . ?
O2 S1 1.424(3) . ?
O3 S1 1.427(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 C1 C6 120.1(4) . . ?
C2 C1 Bi1 124.7(3) . . ?
C6 C1 Bi1 115.1(3) . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 C7 120.1(4) . . ?
C5 C6 C7 120.6(4) . . ?
N1 C7 C6 111.3(3) . . ?
N1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 108.6(4) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C14 118.6(5) . . ?
C10 C9 C8 122.0(4) . . ?
C14 C9 C8 119.2(4) . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.5(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.5(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.7(4) . . ?
C13 C14 Bi1 127.1(3) . . ?
C9 C14 Bi1 112.1(4) . . ?
N1 C15 C16 115.7(4) . . ?
N1 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
N1 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
C17 C16 C21 118.2(5) . . ?
C17 C16 C15 119.7(4) . . ?
C21 C16 C15 122.1(4) . . ?
C18 C17 C16 120.6(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.6(5) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.5(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.1(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 121.1(5) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
F2 C22 F3 107.7(4) . . ?
F2 C22 F1 107.4(4) . . ?
F3 C22 F1 107.8(5) . . ?
F2 C22 S1 111.5(4) . . ?
F3 C22 S1 111.3(3) . . ?
F1 C22 S1 111.0(4) . . ?
C15 N1 C8 112.5(4) . . ?
C15 N1 C7 108.1(3) . . ?
C8 N1 C7 110.4(4) . . ?
C15 N1 Bi1 116.8(3) . . ?
C8 N1 Bi1 102.1(2) . . ?
C7 N1 Bi1 106.7(3) . . ?
S1 O1 Bi1 149.4(2) . . ?
O2 S1 O3 116.8(2) . . ?
O2 S1 O1 113.72(19) . . ?
O3 S1 O1 114.9(2) . . ?
O2 S1 C22 103.8(2) . . ?
O3 S1 C22 104.4(2) . . ?
O1 S1 C22 100.5(2) . . ?
C1 Bi1 C14 96.44(16) . . ?
C1 Bi1 N1 75.86(14) . . ?
C14 Bi1 N1 73.74(15) . . ?
C1 Bi1 O1 84.18(14) . . ?
C14 Bi1 O1 83.20(14) . . ?
N1 Bi1 O1 147.27(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.9(8) . . . . ?
Bi1 C1 C2 C3 -177.8(4) . . . . ?
C1 C2 C3 C4 2.2(8) . . . . ?
C2 C3 C4 C5 -1.9(8) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C2 C1 C6 C5 1.1(8) . . . . ?
Bi1 C1 C6 C5 177.4(4) . . . . ?
C2 C1 C6 C7 176.3(5) . . . . ?
Bi1 C1 C6 C7 -7.4(6) . . . . ?
C4 C5 C6 C1 -0.8(8) . . . . ?
C4 C5 C6 C7 -175.9(5) . . . . ?
C1 C6 C7 N1 30.9(6) . . . . ?
C5 C6 C7 N1 -154.0(4) . . . . ?
N1 C8 C9 C10 -138.0(4) . . . . ?
N1 C8 C9 C14 37.0(5) . . . . ?
C14 C9 C10 C11 0.2(6) . . . . ?
C8 C9 C10 C11 175.3(4) . . . . ?
C9 C10 C11 C12 0.7(7) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C11 C12 C13 C14 -1.3(7) . . . . ?
C12 C13 C14 C9 2.2(7) . . . . ?
C12 C13 C14 Bi1 -174.8(3) . . . . ?
C10 C9 C14 C13 -1.7(6) . . . . ?
C8 C9 C14 C13 -176.9(4) . . . . ?
C10 C9 C14 Bi1 175.8(3) . . . . ?
C8 C9 C14 Bi1 0.6(5) . . . . ?
N1 C15 C16 C17 92.5(5) . . . . ?
N1 C15 C16 C21 -90.5(6) . . . . ?
C21 C16 C17 C18 0.9(7) . . . . ?
C15 C16 C17 C18 178.1(5) . . . . ?
C16 C17 C18 C19 -0.5(8) . . . . ?
C17 C18 C19 C20 0.1(8) . . . . ?
C18 C19 C20 C21 -0.1(8) . . . . ?
C19 C20 C21 C16 0.6(8) . . . . ?
C17 C16 C21 C20 -0.9(8) . . . . ?
C15 C16 C21 C20 -178.0(5) . . . . ?
C16 C15 N1 C8 69.9(5) . . . . ?
C16 C15 N1 C7 -167.9(3) . . . . ?
C16 C15 N1 Bi1 -47.7(4) . . . . ?
C9 C8 N1 C15 -176.6(3) . . . . ?
C9 C8 N1 C7 62.6(4) . . . . ?
C9 C8 N1 Bi1 -50.5(4) . . . . ?
C6 C7 N1 C15 91.3(4) . . . . ?
C6 C7 N1 C8 -145.4(4) . . . . ?
C6 C7 N1 Bi1 -35.1(4) . . . . ?
Bi1 O1 S1 O2 89.3(4) . . . . ?
Bi1 O1 S1 O3 -48.9(4) . . . . ?
Bi1 O1 S1 C22 -160.4(4) . . . . ?
F2 C22 S1 O2 176.8(3) . . . . ?
F3 C22 S1 O2 -63.0(4) . . . . ?
F1 C22 S1 O2 57.1(4) . . . . ?
F2 C22 S1 O3 -60.3(4) . . . . ?
F3 C22 S1 O3 59.9(4) . . . . ?
F1 C22 S1 O3 180.0(3) . . . . ?
F2 C22 S1 O1 59.0(4) . . . . ?
F3 C22 S1 O1 179.2(3) . . . . ?
F1 C22 S1 O1 -60.7(4) . . . . ?

_refine_diff_density_max         1.049
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.145

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1520802'
_audit_update_record             
;
2017-02-21 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 Bi N2 O3'
_chemical_formula_sum            'C21 H19 Bi N2 O3'
_chemical_formula_weight         556.36

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'
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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.6340(4)
_cell_length_b                   10.1839(6)
_cell_length_c                   19.5747(10)
_cell_angle_alpha                91.790(4)
_cell_angle_beta                 104.227(4)
_cell_angle_gamma                93.993(4)
_cell_volume                     1854.76(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    6510
_cell_measurement_theta_min      3.4720
_cell_measurement_theta_max      27.8400

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    9.530
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   
;
 ?
;
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13118
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.014
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6521
_reflns_number_gt                5615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;Brandenburg, K. [or Brandenburg, K. & Putz, H., or Brandenburg, K. & Berndt,
 M.] (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
; Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).
 J. Appl. Cryst. 37, 335-338.
;
_refine_special_details          
;
 ?
;
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+32.6319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6521
_refine_ls_number_parameters     475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C14 C 0.2388(9) 0.8405(9) 0.2798(5) 0.025(2) Uani 1 1 d . . . . .
C13 C 0.1554(10) 0.9069(10) 0.2266(5) 0.029(2) Uani 1 1 d . . . . .
H13 H 0.1812 0.9949 0.2210 0.035 Uiso 1 1 calc R U . . .
C12 C 0.0327(10) 0.8439(11) 0.1812(5) 0.033(2) Uani 1 1 d . . . . .
H12 H -0.0253 0.8905 0.1467 0.039 Uiso 1 1 calc R U . . .
C11 C -0.0018(10) 0.7140(11) 0.1875(5) 0.032(2) Uani 1 1 d . . . . .
H11 H -0.0823 0.6713 0.1565 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0817(10) 0.6448(10) 0.2398(6) 0.031(2) Uani 1 1 d . . . . .
H10 H 0.0579 0.5556 0.2434 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2021(9) 0.7086(10) 0.2874(5) 0.029(2) Uani 1 1 d . . . . .
C8 C 0.2790(10) 0.6357(10) 0.3496(6) 0.032(2) Uani 1 1 d . . . . .
H8A H 0.2260 0.6386 0.3858 0.038 Uiso 1 1 calc R U . . .
H8B H 0.2800 0.5441 0.3349 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4615(10) 0.6954(10) 0.4585(6) 0.033(2) Uani 1 1 d . . . . .
H7A H 0.5630 0.7192 0.4783 0.040 Uiso 1 1 calc R U . . .
H7B H 0.4389 0.6085 0.4737 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3753(10) 0.7930(10) 0.4857(5) 0.029(2) Uani 1 1 d . . . . .
C5 C 0.3248(10) 0.7725(11) 0.5450(5) 0.032(2) Uani 1 1 d . . . . .
H5 H 0.3451 0.6961 0.5691 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2447(11) 0.8624(12) 0.5699(6) 0.042(3) Uani 1 1 d . . . . .
H4 H 0.2114 0.8474 0.6099 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2163(11) 0.9740(12) 0.5334(6) 0.041(3) Uani 1 1 d . . . . .
H3 H 0.1612 1.0343 0.5490 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2665(10) 1.0012(11) 0.4737(6) 0.038(3) Uani 1 1 d . . . . .
H2 H 0.2474 1.0785 0.4503 0.046 Uiso 1 1 calc R U . . .
C1 C 0.3478(9) 0.9063(10) 0.4505(5) 0.027(2) Uani 1 1 d . . . . .
C15 C 0.5301(10) 0.6092(10) 0.3535(6) 0.035(3) Uani 1 1 d . . . . .
H15A H 0.5012 0.6048 0.3023 0.042 Uiso 1 1 calc R U . . .
H15B H 0.5193 0.5203 0.3689 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6873(10) 0.6584(10) 0.3768(5) 0.028(2) Uani 1 1 d . . . . .
C21 C 0.7461(10) 0.7406(9) 0.3335(5) 0.025(2) Uani 1 1 d . . . . .
H21 H 0.6879 0.7685 0.2921 0.030 Uiso 1 1 calc R U . . .
C20 C 0.8922(10) 0.7805(10) 0.3525(5) 0.029(2) Uani 1 1 d . . . . .
H20 H 0.9321 0.8326 0.3230 0.035 Uiso 1 1 calc R U . . .
C19 C 0.9776(10) 0.7432(10) 0.4148(5) 0.027(2) Uani 1 1 d . . . . .
H19 H 1.0744 0.7729 0.4285 0.032 Uiso 1 1 calc R U . . .
C18 C 0.9187(10) 0.6618(11) 0.4567(5) 0.033(2) Uani 1 1 d . . . . .
H18 H 0.9770 0.6353 0.4984 0.040 Uiso 1 1 calc R U . . .
C17 C 0.7748(10) 0.6184(10) 0.4381(5) 0.028(2) Uani 1 1 d . . . . .
H17 H 0.7371 0.5624 0.4668 0.034 Uiso 1 1 calc R U . . .
C22 C 0.7561(9) 0.1974(9) 0.2265(4) 0.0178(19) Uani 1 1 d . . . . .
C23 C 0.8683(9) 0.1201(9) 0.2544(4) 0.0193(19) Uani 1 1 d . . . . .
H23 H 0.8662 0.0336 0.2373 0.023 Uiso 1 1 calc R U . . .
C24 C 0.9832(10) 0.1735(10) 0.3080(5) 0.029(2) Uani 1 1 d . . . . .
H24 H 1.0591 0.1228 0.3263 0.034 Uiso 1 1 calc R U . . .
C25 C 0.9853(10) 0.3004(10) 0.3338(5) 0.027(2) Uani 1 1 d . . . . .
H25 H 1.0627 0.3352 0.3697 0.032 Uiso 1 1 calc R U . . .
C26 C 0.8730(10) 0.3775(10) 0.3070(5) 0.029(2) Uani 1 1 d . . . . .
H26 H 0.8739 0.4630 0.3252 0.035 Uiso 1 1 calc R U . . .
C27 C 0.7588(9) 0.3248(9) 0.2522(5) 0.0194(19) Uani 1 1 d . . . . .
C28 C 0.6376(10) 0.4085(9) 0.2190(5) 0.024(2) Uani 1 1 d . . . . .
H28A H 0.5567 0.3912 0.2395 0.029 Uiso 1 1 calc R U . . .
H28B H 0.6698 0.5013 0.2274 0.029 Uiso 1 1 calc R U . . .
C29 C 0.7139(9) 0.4147(8) 0.1088(5) 0.0187(19) Uani 1 1 d . . . . .
H29A H 0.8049 0.4157 0.1438 0.022 Uiso 1 1 calc R U . . .
H29B H 0.7029 0.5031 0.0923 0.022 Uiso 1 1 calc R U . . .
C30 C 0.7142(9) 0.3210(9) 0.0480(4) 0.0172(18) Uani 1 1 d . . . . .
C31 C 0.7692(9) 0.3644(9) -0.0077(5) 0.023(2) Uani 1 1 d . . . . .
H31 H 0.7997 0.4527 -0.0089 0.027 Uiso 1 1 calc R U . . .
C32 C 0.7781(10) 0.2771(10) -0.0604(5) 0.027(2) Uani 1 1 d . . . . .
H32 H 0.8135 0.3068 -0.0978 0.033 Uiso 1 1 calc R U . . .
C33 C 0.7349(9) 0.1446(10) -0.0589(5) 0.026(2) Uani 1 1 d . . . . .
H33 H 0.7421 0.0857 -0.0950 0.032 Uiso 1 1 calc R U . . .
C34 C 0.6808(9) 0.0999(9) -0.0032(5) 0.022(2) Uani 1 1 d . . . . .
H34 H 0.6521 0.0112 -0.0017 0.027 Uiso 1 1 calc R U . . .
C35 C 0.6705(9) 0.1888(9) 0.0495(4) 0.0176(19) Uani 1 1 d . . . . .
C36 C 0.4616(9) 0.4372(9) 0.1053(5) 0.022(2) Uani 1 1 d . . . . .
H36A H 0.4662 0.4529 0.0573 0.027 Uiso 1 1 calc R U . . .
H36B H 0.4607 0.5220 0.1290 0.027 Uiso 1 1 calc R U . . .
C37 C 0.3233(9) 0.3568(8) 0.1033(5) 0.0199(19) Uani 1 1 d . . . . .
C42 C 0.2630(10) 0.2694(9) 0.0468(5) 0.028(2) Uani 1 1 d . . . . .
H42 H 0.3076 0.2608 0.0099 0.034 Uiso 1 1 calc R U . . .
C41 C 0.1358(10) 0.1941(10) 0.0448(6) 0.034(3) Uani 1 1 d . . . . .
H41 H 0.0955 0.1357 0.0064 0.041 Uiso 1 1 calc R U . . .
C40 C 0.0685(10) 0.2051(11) 0.0994(6) 0.037(3) Uani 1 1 d . . . . .
H40 H -0.0162 0.1543 0.0983 0.045 Uiso 1 1 calc R U . . .
C39 C 0.1287(11) 0.2918(11) 0.1548(6) 0.036(3) Uani 1 1 d . . . . .
H39 H 0.0844 0.2992 0.1918 0.044 Uiso 1 1 calc R U . . .
C38 C 0.2533(10) 0.3690(10) 0.1576(5) 0.027(2) Uani 1 1 d . . . . .
H38 H 0.2908 0.4291 0.1955 0.032 Uiso 1 1 calc R U . . .
N1 N 0.4308(8) 0.6917(8) 0.3807(4) 0.0256(18) Uani 1 1 d . . . . .
N2 N 0.3807(11) 1.2028(10) 0.3169(6) 0.0463(12) Uani 1 1 d . . . . .
N3 N 0.5940(7) 0.3742(7) 0.1418(4) 0.0201(16) Uani 1 1 d . . . . .
N4 N 0.6201(9) -0.1594(8) 0.1534(5) 0.030(2) Uani 1 1 d . . . . .
O1 O 0.3341(9) 1.1317(9) 0.3545(5) 0.054(2) Uani 1 1 d . . . . .
O2 O 0.3725(8) 1.3275(8) 0.3262(4) 0.0463(12) Uani 1 1 d . . . . .
O3 O 0.4424(8) 1.1642(8) 0.2739(4) 0.0463(12) Uani 1 1 d . . . . .
O4 O 0.6702(7) -0.0731(7) 0.1218(4) 0.0289(15) Uani 1 1 d . . . . .
O5 O 0.5495(8) -0.1298(7) 0.1973(4) 0.0391(18) Uani 1 1 d . . . . .
O6 O 0.6385(8) -0.2764(7) 0.1405(5) 0.044(2) Uani 1 1 d . . . . .
Bi1 Bi 0.43995(4) 0.92771(4) 0.35459(2) 0.03044(12) Uani 1 1 d . . . . .
Bi2 Bi 0.56682(3) 0.13252(3) 0.13684(2) 0.01695(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C14 C13 1.377(14) . ?
C14 C9 1.387(14) . ?
C14 Bi1 2.230(9) . ?
C13 C12 1.394(14) . ?
C13 H13 0.9300 . ?
C12 C11 1.358(15) . ?
C12 H12 0.9300 . ?
C11 C10 1.383(15) . ?
C11 H11 0.9300 . ?
C10 C9 1.400(13) . ?
C10 H10 0.9300 . ?
C9 C8 1.507(14) . ?
C8 N1 1.503(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 N1 1.477(13) . ?
C7 C6 1.503(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C1 1.370(14) . ?
C6 C5 1.382(14) . ?
C5 C4 1.388(15) . ?
C5 H5 0.9300 . ?
C4 C3 1.369(17) . ?
C4 H4 0.9300 . ?
C3 C2 1.398(16) . ?
C3 H3 0.9300 . ?
C2 C1 1.417(13) . ?
C2 H2 0.9300 . ?
C1 Bi1 2.275(9) . ?
C15 N1 1.496(11) . ?
C15 C16 1.514(13) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.378(14) . ?
C16 C21 1.398(14) . ?
C21 C20 1.392(13) . ?
C21 H21 0.9300 . ?
C20 C19 1.373(14) . ?
C20 H20 0.9300 . ?
C19 C18 1.374(14) . ?
C19 H19 0.9300 . ?
C18 C17 1.381(14) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C22 C27 1.373(12) . ?
C22 C23 1.393(12) . ?
C22 Bi2 2.242(8) . ?
C23 C24 1.390(13) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(14) . ?
C24 H24 0.9300 . ?
C25 C26 1.388(13) . ?
C25 H25 0.9300 . ?
C26 C27 1.397(13) . ?
C26 H26 0.9300 . ?
C27 C28 1.521(12) . ?
C28 N3 1.489(11) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 N3 1.495(11) . ?
C29 C30 1.503(12) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C35 1.386(12) . ?
C30 C31 1.396(12) . ?
C31 C32 1.362(13) . ?
C31 H31 0.9300 . ?
C32 C33 1.388(13) . ?
C32 H32 0.9300 . ?
C33 C34 1.395(13) . ?
C33 H33 0.9300 . ?
C34 C35 1.379(12) . ?
C34 H34 0.9300 . ?
C35 Bi2 2.251(8) . ?
C36 N3 1.498(11) . ?
C36 C37 1.506(12) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C42 1.381(13) . ?
C37 C38 1.397(13) . ?
C42 C41 1.392(14) . ?
C42 H42 0.9300 . ?
C41 C40 1.387(15) . ?
C41 H41 0.9300 . ?
C40 C39 1.360(16) . ?
C40 H40 0.9300 . ?
C39 C38 1.377(14) . ?
C39 H39 0.9300 . ?
C38 H38 0.9300 . ?
N1 Bi1 2.473(8) . ?
N2 O1 1.190(12) . ?
N2 O3 1.213(12) . ?
N2 O2 1.288(12) . ?
N3 Bi2 2.453(7) . ?
N4 O4 1.228(10) . ?
N4 O6 1.244(10) . ?
N4 O5 1.262(11) . ?
O1 Bi1 2.377(8) . ?
O4 Bi2 2.420(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 C14 C9 119.7(9) . . ?
C13 C14 Bi1 124.5(7) . . ?
C9 C14 Bi1 115.7(7) . . ?
C14 C13 C12 120.7(10) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C11 C12 C13 119.7(10) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C11 C10 120.5(9) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C10 C9 120.2(10) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C14 C9 C10 119.1(9) . . ?
C14 C9 C8 121.8(9) . . ?
C10 C9 C8 118.8(9) . . ?
N1 C8 C9 113.2(8) . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
N1 C7 C6 111.3(8) . . ?
N1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C1 C6 C5 119.4(9) . . ?
C1 C6 C7 118.5(9) . . ?
C5 C6 C7 122.1(10) . . ?
C6 C5 C4 122.1(11) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C3 C4 C5 117.6(11) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C3 C2 122.9(10) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C2 C1 117.3(11) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C6 C1 C2 120.7(10) . . ?
C6 C1 Bi1 115.5(7) . . ?
C2 C1 Bi1 123.8(8) . . ?
N1 C15 C16 114.9(8) . . ?
N1 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
N1 C15 H15B 108.5 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C21 119.5(9) . . ?
C17 C16 C15 121.2(10) . . ?
C21 C16 C15 119.3(9) . . ?
C20 C21 C16 119.8(9) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
C19 C20 C21 120.3(9) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C19 C18 119.3(9) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C18 C17 121.4(9) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C16 C17 C18 119.7(10) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C27 C22 C23 120.1(8) . . ?
C27 C22 Bi2 115.1(6) . . ?
C23 C22 Bi2 124.8(6) . . ?
C24 C23 C22 119.4(9) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C25 C24 C23 120.3(9) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.7(9) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C27 119.1(9) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C22 C27 C26 120.4(8) . . ?
C22 C27 C28 119.0(8) . . ?
C26 C27 C28 120.6(8) . . ?
N3 C28 C27 108.1(7) . . ?
N3 C28 H28A 110.1 . . ?
C27 C28 H28A 110.1 . . ?
N3 C28 H28B 110.1 . . ?
C27 C28 H28B 110.1 . . ?
H28A C28 H28B 108.4 . . ?
N3 C29 C30 110.5(7) . . ?
N3 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C35 C30 C31 119.4(8) . . ?
C35 C30 C29 120.2(8) . . ?
C31 C30 C29 120.2(8) . . ?
C32 C31 C30 120.0(9) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C33 120.8(9) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C32 C33 C34 119.8(9) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C35 C34 C33 119.2(9) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C30 120.8(8) . . ?
C34 C35 Bi2 122.6(7) . . ?
C30 C35 Bi2 116.4(6) . . ?
N3 C36 C37 114.2(7) . . ?
N3 C36 H36A 108.7 . . ?
C37 C36 H36A 108.7 . . ?
N3 C36 H36B 108.7 . . ?
C37 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
C42 C37 C38 118.8(9) . . ?
C42 C37 C36 119.7(9) . . ?
C38 C37 C36 121.5(8) . . ?
C37 C42 C41 120.1(10) . . ?
C37 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C40 C41 C42 120.6(10) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C39 C40 C41 118.7(10) . . ?
C39 C40 H40 120.7 . . ?
C41 C40 H40 120.7 . . ?
C40 C39 C38 121.9(10) . . ?
C40 C39 H39 119.1 . . ?
C38 C39 H39 119.1 . . ?
C39 C38 C37 119.9(10) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C7 N1 C15 111.9(8) . . ?
C7 N1 C8 109.6(8) . . ?
C15 N1 C8 108.7(7) . . ?
C7 N1 Bi1 103.0(6) . . ?
C15 N1 Bi1 116.6(6) . . ?
C8 N1 Bi1 106.8(5) . . ?
O1 N2 O3 123.3(10) . . ?
O1 N2 O2 117.3(11) . . ?
O3 N2 O2 119.2(10) . . ?
C28 N3 C29 109.9(7) . . ?
C28 N3 C36 112.5(7) . . ?
C29 N3 C36 109.3(7) . . ?
C28 N3 Bi2 102.8(5) . . ?
C29 N3 Bi2 107.7(5) . . ?
C36 N3 Bi2 114.3(5) . . ?
O4 N4 O6 118.8(9) . . ?
O4 N4 O5 120.4(8) . . ?
O6 N4 O5 120.7(9) . . ?
N2 O1 Bi1 108.5(7) . . ?
N4 O4 Bi2 110.0(5) . . ?
C14 Bi1 C1 93.4(3) . . ?
C14 Bi1 O1 89.2(3) . . ?
C1 Bi1 O1 80.3(4) . . ?
C14 Bi1 N1 75.9(3) . . ?
C1 Bi1 N1 72.3(3) . . ?
O1 Bi1 N1 147.7(3) . . ?
C22 Bi2 C35 96.6(3) . . ?
C22 Bi2 O4 90.4(3) . . ?
C35 Bi2 O4 81.7(3) . . ?
C22 Bi2 N3 72.5(3) . . ?
C35 Bi2 N3 73.8(3) . . ?
O4 Bi2 N3 147.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C14 C13 C12 1.2(14) . . . . ?
Bi1 C14 C13 C12 178.6(7) . . . . ?
C14 C13 C12 C11 -2.7(14) . . . . ?
C13 C12 C11 C10 1.7(14) . . . . ?
C12 C11 C10 C9 0.8(14) . . . . ?
C13 C14 C9 C10 1.2(13) . . . . ?
Bi1 C14 C9 C10 -176.4(7) . . . . ?
C13 C14 C9 C8 -172.6(8) . . . . ?
Bi1 C14 C9 C8 9.8(11) . . . . ?
C11 C10 C9 C14 -2.2(13) . . . . ?
C11 C10 C9 C8 171.7(9) . . . . ?
C14 C9 C8 N1 -27.1(12) . . . . ?
C10 C9 C8 N1 159.1(8) . . . . ?
N1 C7 C6 C1 -34.7(12) . . . . ?
N1 C7 C6 C5 146.0(9) . . . . ?
C1 C6 C5 C4 1.0(15) . . . . ?
C7 C6 C5 C4 -179.7(9) . . . . ?
C6 C5 C4 C3 0.1(15) . . . . ?
C5 C4 C3 C2 -1.2(16) . . . . ?
C4 C3 C2 C1 1.2(15) . . . . ?
C5 C6 C1 C2 -0.9(14) . . . . ?
C7 C6 C1 C2 179.7(9) . . . . ?
C5 C6 C1 Bi1 179.3(7) . . . . ?
C7 C6 C1 Bi1 -0.1(11) . . . . ?
C3 C2 C1 C6 -0.1(14) . . . . ?
C3 C2 C1 Bi1 179.7(7) . . . . ?
N1 C15 C16 C17 89.7(11) . . . . ?
N1 C15 C16 C21 -93.5(11) . . . . ?
C17 C16 C21 C20 0.3(14) . . . . ?
C15 C16 C21 C20 -176.5(8) . . . . ?
C16 C21 C20 C19 -2.3(14) . . . . ?
C21 C20 C19 C18 2.7(14) . . . . ?
C20 C19 C18 C17 -1.1(15) . . . . ?
C21 C16 C17 C18 1.2(14) . . . . ?
C15 C16 C17 C18 177.9(9) . . . . ?
C19 C18 C17 C16 -0.8(15) . . . . ?
C27 C22 C23 C24 -0.6(13) . . . . ?
Bi2 C22 C23 C24 177.1(6) . . . . ?
C22 C23 C24 C25 0.9(14) . . . . ?
C23 C24 C25 C26 0.0(14) . . . . ?
C24 C25 C26 C27 -1.2(14) . . . . ?
C23 C22 C27 C26 -0.7(13) . . . . ?
Bi2 C22 C27 C26 -178.5(7) . . . . ?
C23 C22 C27 C28 177.8(8) . . . . ?
Bi2 C22 C27 C28 0.0(10) . . . . ?
C25 C26 C27 C22 1.6(14) . . . . ?
C25 C26 C27 C28 -176.9(8) . . . . ?
C22 C27 C28 N3 -36.4(11) . . . . ?
C26 C27 C28 N3 142.1(8) . . . . ?
N3 C29 C30 C35 -32.8(11) . . . . ?
N3 C29 C30 C31 152.2(7) . . . . ?
C35 C30 C31 C32 0.7(13) . . . . ?
C29 C30 C31 C32 175.6(8) . . . . ?
C30 C31 C32 C33 -0.9(13) . . . . ?
C31 C32 C33 C34 0.4(14) . . . . ?
C32 C33 C34 C35 0.3(13) . . . . ?
C33 C34 C35 C30 -0.6(13) . . . . ?
C33 C34 C35 Bi2 174.4(6) . . . . ?
C31 C30 C35 C34 0.1(12) . . . . ?
C29 C30 C35 C34 -174.9(8) . . . . ?
C31 C30 C35 Bi2 -175.1(6) . . . . ?
C29 C30 C35 Bi2 9.9(10) . . . . ?
N3 C36 C37 C42 -91.4(10) . . . . ?
N3 C36 C37 C38 89.0(10) . . . . ?
C38 C37 C42 C41 -0.8(13) . . . . ?
C36 C37 C42 C41 179.5(8) . . . . ?
C37 C42 C41 C40 -0.4(14) . . . . ?
C42 C41 C40 C39 0.5(15) . . . . ?
C41 C40 C39 C38 0.5(15) . . . . ?
C40 C39 C38 C37 -1.6(15) . . . . ?
C42 C37 C38 C39 1.7(13) . . . . ?
C36 C37 C38 C39 -178.6(8) . . . . ?
C6 C7 N1 C15 172.1(8) . . . . ?
C6 C7 N1 C8 -67.3(10) . . . . ?
C6 C7 N1 Bi1 46.1(8) . . . . ?
C16 C15 N1 C7 -62.4(12) . . . . ?
C16 C15 N1 C8 176.5(9) . . . . ?
C16 C15 N1 Bi1 55.8(11) . . . . ?
C9 C8 N1 C7 138.0(8) . . . . ?
C9 C8 N1 C15 -99.5(9) . . . . ?
C9 C8 N1 Bi1 27.2(9) . . . . ?
C27 C28 N3 C29 -65.9(9) . . . . ?
C27 C28 N3 C36 172.0(7) . . . . ?
C27 C28 N3 Bi2 48.5(7) . . . . ?
C30 C29 N3 C28 147.2(7) . . . . ?
C30 C29 N3 C36 -88.8(8) . . . . ?
C30 C29 N3 Bi2 35.9(8) . . . . ?
C37 C36 N3 C28 -88.7(9) . . . . ?
C37 C36 N3 C29 148.9(8) . . . . ?
C37 C36 N3 Bi2 28.1(9) . . . . ?
O3 N2 O1 Bi1 16.3(14) . . . . ?
O2 N2 O1 Bi1 -159.0(7) . . . . ?
O6 N4 O4 Bi2 165.9(6) . . . . ?
O5 N4 O4 Bi2 -13.0(10) . . . . ?

_refine_diff_density_max         5.518
_refine_diff_density_min         -5.318
_refine_diff_density_rms         0.200

# start Validation Reply Form
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Residual Density  0.62A From     Bi1       5.08 eA-3  
RESPONSE:

The highest unrefined electron density peaks (Q peaks) are located at:
0.84 A from Bi1 (Q1, 5.5 e A-3),
1.39 A from Bi1 (Q2, 1.3 e A-3),
1.40 A from Bi1 (Q3, 1.2 e A-3),
0.94 A from Bi2 (Q4, 1.2 e A-3),
1.28 A from Bi1 (Q5, 1.2 e A-3) and
1.29 A from N1 (Q6, 1.0 e A-3).

Acoording to W. Massa (Kristallstrukturbestimmung, Teubner Studienbuecher, 
Stuttgart, 1996) and W. Clegg (Crystal Structure Determination, Oxford 
University Press, 1998) this might be observed for heavy atoms for which 
remaining density peaks with ca. 10% of the electron density of the heavy 
atom are expected at distances between 0.6 and 1.2 A. Most likely, this
accounts for Q1 in the proximity of Bi1 and for Q4 in the proximity of Bi2.
Remaining Q peaks corresponds then
to usually observed unrefined electron density peaks.

;
_vrf_PLAT972_shelx               
;
PROBLEM: Check Calcd Residual Density  0.66A From     Bi1      -4.95 eA-3  
RESPONSE: cf. above
;
# end Validation Reply Form


_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1520799'
_audit_update_record             
;
2017-02-21 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 Bi N2 O3'
_chemical_formula_sum            'C22 H21 Bi N2 O3'
_chemical_formula_weight         570.39

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'
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                   9.567(3)
_cell_length_b                   18.155(5)
_cell_length_c                   12.596(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.952(5)
_cell_angle_gamma                90
_cell_volume                     2043.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2748
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      20.54

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    8.654
_shelx_estimated_absorpt_T_min   0.157
_shelx_estimated_absorpt_T_max   0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.157
_exptl_absorpt_correction_T_max  0.231
_exptl_absorpt_process_details   
; SADABS - V2.03 (Bruker 2001)was used for 
absorption  correction. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14421
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.063
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3608
_reflns_number_gt                2939
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    
;Brandenburg, K. [or Brandenburg, K. & Putz, H., or Brandenburg, K. & Berndt,
 M.] (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
; Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).
 J. Appl. Cryst. 37, 335-338.
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+2.0027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3608
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.16421(3) 0.11956(2) 0.10188(2) 0.03636(11) Uani 1 1 d . . . . .
C1 C 0.3775(7) 0.1544(4) 0.0792(5) 0.0354(16) Uani 1 1 d . . . . .
C6 C 0.4580(8) 0.2107(4) 0.1524(5) 0.0362(16) Uani 1 1 d . . . . .
C5 C 0.5996(8) 0.2285(4) 0.1509(7) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.6547 0.2659 0.1979 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6588(9) 0.1915(5) 0.0808(7) 0.063(3) Uani 1 1 d . . . . .
H4 H 0.7527 0.2045 0.0807 0.076 Uiso 1 1 calc R U . . .
C3 C 0.5799(10) 0.1356(5) 0.0111(8) 0.060(2) Uani 1 1 d . . . . .
H3 H 0.6211 0.1103 -0.0349 0.072 Uiso 1 1 calc R U . . .
C2 C 0.4386(9) 0.1171(4) 0.0100(6) 0.0477(19) Uani 1 1 d . . . . .
H2 H 0.3847 0.0796 -0.0373 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3880(8) 0.2535(4) 0.2222(6) 0.0413(18) Uani 1 1 d . . . . .
H7A H 0.4662 0.2729 0.2888 0.050 Uiso 1 1 calc R U . . .
H7B H 0.3331 0.2949 0.1779 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0391(7) 0.2263(3) 0.0526(6) 0.0350(16) Uani 1 1 d . . . . .
C9 C 0.0540(8) 0.2743(4) 0.1427(6) 0.0411(18) Uani 1 1 d . . . . .
C10 C -0.0245(9) 0.3408(4) 0.1233(7) 0.057(2) Uani 1 1 d . . . . .
H10 H -0.0102 0.3732 0.1834 0.068 Uiso 1 1 calc R U . . .
C11 C -0.1231(9) 0.3592(4) 0.0162(7) 0.056(2) Uani 1 1 d . . . . .
H11 H -0.1790 0.4023 0.0041 0.067 Uiso 1 1 calc R U . . .
C12 C -0.1361(8) 0.3114(4) -0.0723(6) 0.054(2) Uani 1 1 d . . . . .
H12 H -0.1965 0.3247 -0.1457 0.065 Uiso 1 1 calc R U . . .
C13 C -0.0634(8) 0.2457(4) -0.0556(6) 0.0433(18) Uani 1 1 d . . . . .
H13 H -0.0815 0.2132 -0.1161 0.052 Uiso 1 1 calc R U . . .
C8 C 0.1563(9) 0.2548(4) 0.2619(6) 0.049(2) Uani 1 1 d . . . . .
H8A H 0.1956 0.2995 0.3041 0.059 Uiso 1 1 calc R U . . .
H8B H 0.0999 0.2287 0.3006 0.059 Uiso 1 1 calc R U . . .
C15 C 0.3679(8) 0.1734(4) 0.3710(5) 0.0442(19) Uani 1 1 d . . . . .
H15A H 0.3990 0.2120 0.4280 0.053 Uiso 1 1 calc R U . . .
H15B H 0.4577 0.1504 0.3674 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2787(11) 0.1156(4) 0.4089(7) 0.063(2) Uani 1 1 d . . . . .
H16A H 0.1868 0.1380 0.4092 0.076 Uiso 1 1 calc R U . . .
H16B H 0.2517 0.0759 0.3538 0.076 Uiso 1 1 calc R U . . .
C17 C 0.3617(10) 0.0838(4) 0.5249(6) 0.047(2) Uani 1 1 d . . . . .
C18 C 0.2759(11) 0.0520(4) 0.5809(7) 0.063(2) Uani 1 1 d . . . . .
H18 H 0.1723 0.0516 0.5457 0.076 Uiso 1 1 calc R U . . .
C19 C 0.3392(16) 0.0209(5) 0.6867(10) 0.090(3) Uani 1 1 d . . . . .
H19 H 0.2789 -0.0018 0.7207 0.107 Uiso 1 1 calc R U . . .
C20 C 0.4909(17) 0.0233(5) 0.7421(8) 0.093(4) Uani 1 1 d . . . . .
H20 H 0.5341 0.0034 0.8146 0.112 Uiso 1 1 calc R U . . .
C21 C 0.5797(13) 0.0560(5) 0.6885(8) 0.083(3) Uani 1 1 d . . . . .
H21 H 0.6828 0.0585 0.7259 0.099 Uiso 1 1 calc R U . . .
C22 C 0.5153(11) 0.0849(5) 0.5794(7) 0.064(2) Uani 1 1 d . . . . .
H22 H 0.5758 0.1051 0.5432 0.077 Uiso 1 1 calc R U . . .
N1 N 0.2839(6) 0.2073(3) 0.2590(5) 0.0410(14) Uani 1 1 d . . . . .
N2 N 0.0767(8) 0.0244(4) -0.1206(6) 0.0560(18) Uani 1 1 d . . . . .
O1 O 0.0700(6) 0.0927(3) -0.1000(4) 0.0569(15) Uani 1 1 d . . . . .
O2 O 0.0137(8) 0.0006(3) -0.2187(5) 0.084(2) Uani 1 1 d . . . . .
O3 O 0.1448(7) -0.0170(3) -0.0396(6) 0.0784(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C14 2.246(6) . ?
Bi1 C1 2.250(7) . ?
Bi1 O1 2.424(5) . ?
Bi1 N1 2.479(5) . ?
C1 C2 1.387(9) . ?
C1 C6 1.407(9) . ?
C6 C5 1.399(9) . ?
C6 C7 1.498(9) . ?
C5 C4 1.382(11) . ?
C5 H5 0.9300 . ?
C4 C3 1.378(12) . ?
C4 H4 0.9300 . ?
C3 C2 1.388(11) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 N1 1.496(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C9 1.396(9) . ?
C14 C13 1.410(9) . ?
C9 C10 1.396(10) . ?
C9 C8 1.512(10) . ?
C10 C11 1.383(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C8 N1 1.506(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 N1 1.486(8) . ?
C15 C16 1.532(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.506(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.382(11) . ?
C17 C18 1.385(11) . ?
C18 C19 1.372(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(15) . ?
C19 H19 0.9300 . ?
C20 C21 1.392(14) . ?
C20 H20 0.9300 . ?
C21 C22 1.393(11) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N2 O2 1.243(8) . ?
N2 O3 1.247(8) . ?
N2 O1 1.273(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
C14 Bi1 C1 98.1(2) . . ?
C14 Bi1 O1 85.6(2) . . ?
C1 Bi1 O1 86.4(2) . . ?
C14 Bi1 N1 73.4(2) . . ?
C1 Bi1 N1 74.9(2) . . ?
O1 Bi1 N1 149.20(17) . . ?
C2 C1 C6 120.7(7) . . ?
C2 C1 Bi1 123.2(5) . . ?
C6 C1 Bi1 115.4(5) . . ?
C5 C6 C1 117.7(7) . . ?
C5 C6 C7 121.7(7) . . ?
C1 C6 C7 120.4(6) . . ?
C4 C5 C6 121.1(8) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C3 C4 C5 120.6(7) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C3 C2 119.6(8) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C1 C2 C3 120.2(7) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N1 C7 C6 112.2(5) . . ?
N1 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C14 C13 117.6(6) . . ?
C9 C14 Bi1 115.1(5) . . ?
C13 C14 Bi1 126.9(5) . . ?
C10 C9 C14 120.3(7) . . ?
C10 C9 C8 119.5(7) . . ?
C14 C9 C8 120.2(6) . . ?
C11 C10 C9 121.1(8) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 117.9(7) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C13 C12 C11 122.2(7) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 120.6(7) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
N1 C8 C9 110.6(6) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N1 C15 C16 114.0(6) . . ?
N1 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 113.9(7) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C22 C17 C18 118.2(8) . . ?
C22 C17 C16 125.0(8) . . ?
C18 C17 C16 116.8(8) . . ?
C19 C18 C17 122.0(10) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C20 C19 C18 120.1(11) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.1(10) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C22 120.6(10) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 120.0(9) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C15 N1 C7 109.4(5) . . ?
C15 N1 C8 112.4(5) . . ?
C7 N1 C8 108.8(5) . . ?
C15 N1 Bi1 115.5(4) . . ?
C7 N1 Bi1 106.3(4) . . ?
C8 N1 Bi1 103.9(4) . . ?
O2 N2 O3 122.0(7) . . ?
O2 N2 O1 120.0(7) . . ?
O3 N2 O1 118.0(7) . . ?
N2 O1 Bi1 112.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 1.3(10) . . . . ?
Bi1 C1 C6 C5 172.8(5) . . . . ?
C2 C1 C6 C7 176.6(6) . . . . ?
Bi1 C1 C6 C7 -11.8(8) . . . . ?
C1 C6 C5 C4 -0.6(10) . . . . ?
C7 C6 C5 C4 -175.9(7) . . . . ?
C6 C5 C4 C3 -0.5(12) . . . . ?
C5 C4 C3 C2 1.1(12) . . . . ?
C6 C1 C2 C3 -0.8(10) . . . . ?
Bi1 C1 C2 C3 -171.6(5) . . . . ?
C4 C3 C2 C1 -0.4(12) . . . . ?
C5 C6 C7 N1 -151.1(6) . . . . ?
C1 C6 C7 N1 33.7(8) . . . . ?
C13 C14 C9 C10 -3.5(10) . . . . ?
Bi1 C14 C9 C10 -176.8(5) . . . . ?
C13 C14 C9 C8 176.9(6) . . . . ?
Bi1 C14 C9 C8 3.6(8) . . . . ?
C14 C9 C10 C11 2.8(12) . . . . ?
C8 C9 C10 C11 -177.6(7) . . . . ?
C9 C10 C11 C12 -3.2(12) . . . . ?
C10 C11 C12 C13 4.5(12) . . . . ?
C11 C12 C13 C14 -5.5(12) . . . . ?
C9 C14 C13 C12 4.8(10) . . . . ?
Bi1 C14 C13 C12 177.2(6) . . . . ?
C10 C9 C8 N1 -150.3(7) . . . . ?
C14 C9 C8 N1 29.3(9) . . . . ?
N1 C15 C16 C17 -177.4(6) . . . . ?
C15 C16 C17 C22 -20.6(11) . . . . ?
C15 C16 C17 C18 158.4(7) . . . . ?
C22 C17 C18 C19 -1.2(12) . . . . ?
C16 C17 C18 C19 179.7(8) . . . . ?
C17 C18 C19 C20 2.6(14) . . . . ?
C18 C19 C20 C21 -1.6(15) . . . . ?
C19 C20 C21 C22 -0.9(14) . . . . ?
C18 C17 C22 C21 -1.2(12) . . . . ?
C16 C17 C22 C21 177.8(8) . . . . ?
C20 C21 C22 C17 2.3(13) . . . . ?
C16 C15 N1 C7 -171.1(6) . . . . ?
C16 C15 N1 C8 67.8(8) . . . . ?
C16 C15 N1 Bi1 -51.2(8) . . . . ?
C6 C7 N1 C15 90.8(7) . . . . ?
C6 C7 N1 C8 -145.9(6) . . . . ?
C6 C7 N1 Bi1 -34.6(6) . . . . ?
C9 C8 N1 C15 -167.4(6) . . . . ?
C9 C8 N1 C7 71.2(7) . . . . ?
C9 C8 N1 Bi1 -41.8(6) . . . . ?
O2 N2 O1 Bi1 169.9(6) . . . . ?
O3 N2 O1 Bi1 -8.6(8) . . . . ?

_refine_diff_density_max         0.906
_refine_diff_density_min         -1.214
_refine_diff_density_rms         0.131



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1520800'
_audit_update_record             
;
2017-02-21 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H26 Bi N O3 S'
_chemical_formula_weight         677.55

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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.0680(11)
_cell_length_b                   14.0151(13)
_cell_length_c                   15.1158(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.579(2)
_cell_angle_gamma                90
_cell_volume                     2555.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4921
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      22.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.370
_exptl_absorpt_coefficient_mu    7.012
_shelx_estimated_absorpt_T_min   0.106
_shelx_estimated_absorpt_T_max   0.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.106
_exptl_absorpt_correction_T_max  0.181
_exptl_absorpt_process_details   
; SADABS - V2.03 (Bruker 2001)was used for 
absorption  correction. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23643
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4497
_reflns_number_gt                3578
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    
;Brandenburg, K. [or Brandenburg, K. & Putz, H., or Brandenburg, K. & Berndt,
 M.] (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material  
; Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).
 J. Appl. Cryst. 37, 335-338.
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4497
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 0.56135(2) 0.69977(2) 0.10469(2) 0.04003(9) Uani 1 1 d . . . . .
C14 C 0.4752(5) 0.8095(4) 0.1848(4) 0.0435(14) Uani 1 1 d . . . . .
C9 C 0.3844(5) 0.8545(4) 0.1443(4) 0.0449(14) Uani 1 1 d . . . . .
C10 C 0.3351(5) 0.9299(4) 0.1862(4) 0.0584(17) Uani 1 1 d . . . . .
H10 H 0.2739 0.9602 0.1601 0.070 Uiso 1 1 calc R U . . .
C11 C 0.3769(6) 0.9602(5) 0.2670(5) 0.075(2) Uani 1 1 d . . . . .
H11 H 0.3441 1.0119 0.2946 0.089 Uiso 1 1 calc R U . . .
C12 C 0.4640(6) 0.9166(5) 0.3071(4) 0.071(2) Uani 1 1 d . . . . .
H12 H 0.4895 0.9375 0.3624 0.086 Uiso 1 1 calc R U . . .
C13 C 0.5158(5) 0.8410(4) 0.2666(4) 0.0597(17) Uani 1 1 d . . . . .
H13 H 0.5769 0.8117 0.2937 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3385(4) 0.8143(4) 0.0571(4) 0.0493(15) Uani 1 1 d . . . . .
H8A H 0.2881 0.7622 0.0690 0.059 Uiso 1 1 calc R U . . .
H8B H 0.2972 0.8635 0.0254 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3904(5) 0.7022(4) -0.0584(4) 0.0526(15) Uani 1 1 d . . . . .
H7A H 0.4450 0.6888 -0.1026 0.063 Uiso 1 1 calc R U . . .
H7B H 0.3225 0.7225 -0.0887 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3688(4) 0.6138(4) -0.0060(4) 0.0445(14) Uani 1 1 d . . . . .
C1 C 0.4268(4) 0.5946(4) 0.0725(3) 0.0399(12) Uani 1 1 d . . . . .
C2 C 0.4069(5) 0.5119(4) 0.1168(4) 0.0521(15) Uani 1 1 d . . . . .
H2 H 0.4474 0.4993 0.1687 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3298(5) 0.4467(4) 0.0879(5) 0.0619(18) Uani 1 1 d . . . . .
H3 H 0.3169 0.3914 0.1200 0.074 Uiso 1 1 calc R U . . .
C4 C 0.2721(5) 0.4647(5) 0.0107(5) 0.0625(18) Uani 1 1 d . . . . .
H4 H 0.2207 0.4204 -0.0107 0.075 Uiso 1 1 calc R U . . .
C5 C 0.2893(5) 0.5476(4) -0.0357(4) 0.0561(16) Uani 1 1 d . . . . .
H5 H 0.2478 0.5598 -0.0872 0.067 Uiso 1 1 calc R U . . .
C15 C 0.4749(5) 0.8627(4) -0.0476(4) 0.0522(15) Uani 1 1 d . . . . .
H15A H 0.4814 0.9162 -0.0070 0.063 Uiso 1 1 calc R U . . .
H15B H 0.4221 0.8802 -0.0943 0.063 Uiso 1 1 calc R U . . .
C16 C 0.5858(5) 0.8451(4) -0.0875(4) 0.0429(14) Uani 1 1 d . . . . .
C21 C 0.6815(6) 0.8635(5) -0.0383(4) 0.073(2) Uani 1 1 d . . . . .
H21 H 0.6768 0.8862 0.0193 0.087 Uiso 1 1 calc R U . . .
C20 C 0.7844(6) 0.8484(6) -0.0739(7) 0.101(3) Uani 1 1 d . . . . .
H20 H 0.8484 0.8602 -0.0399 0.121 Uiso 1 1 calc R U . . .
C19 C 0.7924(8) 0.8163(6) -0.1590(8) 0.106(4) Uani 1 1 d . . . . .
H19 H 0.8614 0.8069 -0.1834 0.127 Uiso 1 1 calc R U . . .
C18 C 0.6974(8) 0.7982(5) -0.2079(6) 0.088(3) Uani 1 1 d . . . . .
H18 H 0.7015 0.7756 -0.2655 0.105 Uiso 1 1 calc R U . . .
C17 C 0.5975(6) 0.8134(4) -0.1718(4) 0.0606(17) Uani 1 1 d . . . . .
H17 H 0.5339 0.8017 -0.2062 0.073 Uiso 1 1 calc R U . . .
C22 C 0.6243(4) 0.4706(4) 0.3303(4) 0.0432(14) Uani 1 1 d . . . . .
C23 C 0.6785(4) 0.3910(4) 0.3017(4) 0.0498(14) Uani 1 1 d . . . . .
H23 H 0.7416 0.3966 0.2681 0.060 Uiso 1 1 calc R U . . .
C24 C 0.6370(6) 0.3006(5) 0.3240(5) 0.0636(18) Uani 1 1 d . . . . .
H24 H 0.6717 0.2468 0.3018 0.076 Uiso 1 1 calc R U . . .
C25 C 0.5525(6) 0.2889(4) 0.3741(4) 0.0583(17) Uani 1 1 d . . . . .
C26 C 0.4948(6) 0.3698(5) 0.4026(4) 0.072(2) Uani 1 1 d . . . . .
H26 H 0.4320 0.3629 0.4362 0.086 Uiso 1 1 calc R U . . .
C27 C 0.5322(5) 0.4602(5) 0.3803(4) 0.0646(18) Uani 1 1 d . . . . .
H27 H 0.4944 0.5139 0.3993 0.078 Uiso 1 1 calc R U . . .
C28 C 0.5174(7) 0.1912(6) 0.3990(6) 0.094(3) Uani 1 1 d . . . . .
H28 H 0.5469 0.1426 0.3650 0.113 Uiso 1 1 calc R U . . .
C29 C 0.4576(7) 0.1649(7) 0.4556(7) 0.116(3) Uani 1 1 d . . . . .
H29A H 0.4248 0.2091 0.4926 0.139 Uiso 1 1 calc R U . . .
H29B H 0.4437 0.1001 0.4628 0.139 Uiso 1 1 calc R U . . .
N1 N 0.4312(3) 0.7788(3) 0.0009(3) 0.0425(11) Uani 1 1 d . . . . .
O1 O 0.5797(3) 0.6209(3) 0.2431(3) 0.0693(13) Uani 1 1 d . . . . .
O2 O 0.7712(4) 0.5758(4) 0.2558(4) 0.1084(19) Uani 1 1 d . . . . .
O3 O 0.6766(5) 0.6394(3) 0.3808(3) 0.1017(18) Uani 1 1 d . . . . .
S1 S 0.66998(14) 0.58554(11) 0.30103(11) 0.0581(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C14 2.232(5) . ?
Bi1 C1 2.237(5) . ?
Bi1 O1 2.371(4) . ?
Bi1 N1 2.454(4) . ?
C14 C13 1.389(8) . ?
C14 C9 1.391(7) . ?
C9 C10 1.375(7) . ?
C9 C8 1.523(8) . ?
C10 C11 1.376(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.346(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C8 N1 1.508(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 N1 1.474(6) . ?
C7 C6 1.496(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C1 1.387(7) . ?
C6 C5 1.400(7) . ?
C1 C2 1.363(7) . ?
C2 C3 1.367(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C15 N1 1.490(6) . ?
C15 C16 1.503(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.360(8) . ?
C16 C21 1.381(8) . ?
C21 C20 1.383(10) . ?
C21 H21 0.9300 . ?
C20 C19 1.370(12) . ?
C20 H20 0.9300 . ?
C19 C18 1.370(12) . ?
C19 H19 0.9300 . ?
C18 C17 1.353(9) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C22 C27 1.368(8) . ?
C22 C23 1.369(7) . ?
C22 S1 1.763(5) . ?
C23 C24 1.407(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.297(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.404(9) . ?
C25 C28 1.484(9) . ?
C26 C27 1.390(8) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.193(10) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9300 . ?
C29 H29B 0.9300 . ?
O1 S1 1.465(4) . ?
O2 S1 1.422(5) . ?
O3 S1 1.423(5) . ?

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 Bi1 C1 103.06(19) . . ?
C14 Bi1 O1 82.89(18) . . ?
C1 Bi1 O1 86.24(17) . . ?
C14 Bi1 N1 74.71(18) . . ?
C1 Bi1 N1 73.13(17) . . ?
O1 Bi1 N1 144.79(14) . . ?
C13 C14 C9 120.1(5) . . ?
C13 C14 Bi1 123.0(4) . . ?
C9 C14 Bi1 116.5(4) . . ?
C10 C9 C14 119.4(6) . . ?
C10 C9 C8 122.0(5) . . ?
C14 C9 C8 118.4(5) . . ?
C9 C10 C11 119.5(6) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.5(6) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.4(7) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 119.1(6) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
N1 C8 C9 110.6(4) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N1 C7 C6 110.0(5) . . ?
N1 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C1 C6 C5 118.1(5) . . ?
C1 C6 C7 121.5(5) . . ?
C5 C6 C7 120.4(5) . . ?
C2 C1 C6 119.6(5) . . ?
C2 C1 Bi1 126.1(4) . . ?
C6 C1 Bi1 113.8(4) . . ?
C1 C2 C3 122.6(6) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C4 C3 C2 118.4(6) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 120.7(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.5(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N1 C15 C16 113.5(4) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C21 117.3(6) . . ?
C17 C16 C15 123.1(5) . . ?
C21 C16 C15 119.6(6) . . ?
C16 C21 C20 120.5(7) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C19 C20 C21 120.2(8) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C19 C18 119.2(8) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C17 C18 C19 119.7(8) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C17 C16 123.1(7) . . ?
C18 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C27 C22 C23 119.3(5) . . ?
C27 C22 S1 120.0(5) . . ?
C23 C22 S1 120.6(5) . . ?
C22 C23 C24 118.8(6) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 123.0(6) . . ?
C25 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
C24 C25 C26 118.7(6) . . ?
C24 C25 C28 120.0(7) . . ?
C26 C25 C28 121.3(7) . . ?
C27 C26 C25 119.7(6) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C22 C27 C26 120.3(6) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C25 130.5(10) . . ?
C29 C28 H28 114.7 . . ?
C25 C28 H28 114.7 . . ?
C28 C29 H29A 120.0 . . ?
C28 C29 H29B 120.0 . . ?
H29A C29 H29B 120.0 . . ?
C7 N1 C15 113.2(4) . . ?
C7 N1 C8 110.0(4) . . ?
C15 N1 C8 107.1(4) . . ?
C7 N1 Bi1 104.9(3) . . ?
C15 N1 Bi1 116.2(3) . . ?
C8 N1 Bi1 105.1(3) . . ?
S1 O1 Bi1 137.3(3) . . ?
O2 S1 O3 115.4(4) . . ?
O2 S1 O1 112.3(3) . . ?
O3 S1 O1 110.5(3) . . ?
O2 S1 C22 108.2(3) . . ?
O3 S1 C22 106.4(3) . . ?
O1 S1 C22 103.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C14 C9 C10 -0.3(8) . . . . ?
Bi1 C14 C9 C10 -173.0(4) . . . . ?
C13 C14 C9 C8 -176.6(5) . . . . ?
Bi1 C14 C9 C8 10.7(6) . . . . ?
C14 C9 C10 C11 0.6(8) . . . . ?
C8 C9 C10 C11 176.7(5) . . . . ?
C9 C10 C11 C12 -1.2(10) . . . . ?
C10 C11 C12 C13 1.6(11) . . . . ?
C11 C12 C13 C14 -1.3(10) . . . . ?
C9 C14 C13 C12 0.6(9) . . . . ?
Bi1 C14 C13 C12 172.8(4) . . . . ?
C10 C9 C8 N1 146.7(5) . . . . ?
C14 C9 C8 N1 -37.1(6) . . . . ?
N1 C7 C6 C1 -27.8(7) . . . . ?
N1 C7 C6 C5 152.5(5) . . . . ?
C5 C6 C1 C2 1.6(8) . . . . ?
C7 C6 C1 C2 -178.1(5) . . . . ?
C5 C6 C1 Bi1 174.7(4) . . . . ?
C7 C6 C1 Bi1 -5.0(6) . . . . ?
C6 C1 C2 C3 -1.3(9) . . . . ?
Bi1 C1 C2 C3 -173.4(4) . . . . ?
C1 C2 C3 C4 1.2(9) . . . . ?
C2 C3 C4 C5 -1.6(9) . . . . ?
C3 C4 C5 C6 2.0(9) . . . . ?
C1 C6 C5 C4 -1.9(8) . . . . ?
C7 C6 C5 C4 177.7(5) . . . . ?
N1 C15 C16 C17 92.4(6) . . . . ?
N1 C15 C16 C21 -89.2(6) . . . . ?
C17 C16 C21 C20 -1.0(9) . . . . ?
C15 C16 C21 C20 -179.5(6) . . . . ?
C16 C21 C20 C19 0.9(11) . . . . ?
C21 C20 C19 C18 -0.8(12) . . . . ?
C20 C19 C18 C17 0.8(12) . . . . ?
C19 C18 C17 C16 -1.0(11) . . . . ?
C21 C16 C17 C18 1.1(9) . . . . ?
C15 C16 C17 C18 179.5(6) . . . . ?
C27 C22 C23 C24 0.5(8) . . . . ?
S1 C22 C23 C24 -177.8(4) . . . . ?
C22 C23 C24 C25 -3.4(9) . . . . ?
C23 C24 C25 C26 4.5(10) . . . . ?
C23 C24 C25 C28 -176.5(6) . . . . ?
C24 C25 C26 C27 -3.0(10) . . . . ?
C28 C25 C26 C27 178.0(6) . . . . ?
C23 C22 C27 C26 0.8(9) . . . . ?
S1 C22 C27 C26 179.1(5) . . . . ?
C25 C26 C27 C22 0.4(10) . . . . ?
C24 C25 C28 C29 164.4(9) . . . . ?
C26 C25 C28 C29 -16.6(13) . . . . ?
C6 C7 N1 C15 169.0(4) . . . . ?
C6 C7 N1 C8 -71.2(5) . . . . ?
C6 C7 N1 Bi1 41.3(5) . . . . ?
C16 C15 N1 C7 -73.9(6) . . . . ?
C16 C15 N1 C8 164.7(5) . . . . ?
C16 C15 N1 Bi1 47.6(6) . . . . ?
C9 C8 N1 C7 152.8(4) . . . . ?
C9 C8 N1 C15 -83.8(5) . . . . ?
C9 C8 N1 Bi1 40.3(4) . . . . ?
Bi1 O1 S1 O2 -17.8(5) . . . . ?
Bi1 O1 S1 O3 112.7(4) . . . . ?
Bi1 O1 S1 C22 -134.0(4) . . . . ?
C27 C22 S1 O2 175.4(5) . . . . ?
C23 C22 S1 O2 -6.3(5) . . . . ?
C27 C22 S1 O3 50.8(5) . . . . ?
C23 C22 S1 O3 -130.9(5) . . . . ?
C27 C22 S1 O1 -65.5(5) . . . . ?
C23 C22 S1 O1 112.8(5) . . . . ?

_refine_diff_density_max         0.614
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.112



