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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1520814'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Bi Br N O'
_chemical_formula_sum            'C17 H19 Bi Br N O'
_chemical_formula_weight         542.22

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'
Br Br -0.2901 2.4595 '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                   16.777(4)
_cell_length_b                   13.537(4)
_cell_length_c                   16.910(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.416(4)
_cell_angle_gamma                90
_cell_volume                     3497.0(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    297
_cell_measurement_reflns_used    7336
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_F_000             2032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    12.367
_shelx_estimated_absorpt_T_min   0.089
_shelx_estimated_absorpt_T_max   0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;SADABS - V2.03 (Bruker 2001)was used for absorption 
correction. R(int) =  0.1526 before parameter refinement
 and 0.0651 after parameter refinement.  Ratio of 
minimum to maximum apparent transmission:  0.387790
 Lambda/2 correction factor = 0.0015
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297
_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            32639
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.333
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6146
_reflns_number_gt                4708
_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-2016/4 (Sheldrick, 2016)'
_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)+(0.0299P)²+13.3344P] 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         6146
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.34857(3) 0.48288(3) 0.16013(3) 0.02901(13) Uani 1 1 d . . . . .
BI2 Bi 0.14974(3) 0.53513(3) 0.28030(3) 0.03422(14) Uani 1 1 d . . . . .
BR1 Br 0.31778(9) 0.66383(9) 0.06866(9) 0.0576(4) Uani 1 1 d . . . . .
BR2 Br 0.16100(9) 0.35782(9) 0.19459(9) 0.0559(4) Uani 1 1 d . . . . .
C1 C 0.4896(7) 0.4846(8) 0.1796(7) 0.034(3) Uani 1 1 d . . . . .
C6 C 0.5472(7) 0.4340(8) 0.2505(7) 0.038(3) Uani 1 1 d . . . . .
C5 C 0.6352(8) 0.4241(9) 0.2632(9) 0.056(4) Uani 1 1 d . . . . .
H5 H 0.675380 0.390858 0.311277 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6601(10) 0.4650(11) 0.2020(12) 0.073(5) Uani 1 1 d . . . . .
H4 H 0.718181 0.458825 0.210060 0.087 Uiso 1 1 calc R U . . .
C3 C 0.6043(11) 0.5132(10) 0.1317(11) 0.068(4) Uani 1 1 d . . . . .
H3 H 0.622950 0.538571 0.091053 0.081 Uiso 1 1 calc R U . . .
C2 C 0.5164(9) 0.5246(9) 0.1206(8) 0.053(3) Uani 1 1 d . . . . .
H2 H 0.477016 0.559431 0.073170 0.064 Uiso 1 1 calc R U . . .
C7 C 0.5196(7) 0.3924(9) 0.3175(7) 0.045(3) Uani 1 1 d . . . . .
H7A H 0.553852 0.333592 0.342192 0.054 Uiso 1 1 calc R U . . .
H7B H 0.532929 0.440297 0.363920 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3651(6) 0.5578(7) 0.2855(7) 0.027(2) Uani 1 1 d . . . . .
C9 C 0.3845(6) 0.4994(8) 0.3556(7) 0.033(3) Uani 1 1 d . . . . .
C10 C 0.3842(7) 0.5419(9) 0.4329(8) 0.044(3) Uani 1 1 d . . . . .
H10 H 0.394251 0.501649 0.480706 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3695(8) 0.6393(10) 0.4379(8) 0.049(3) Uani 1 1 d . . . . .
H11 H 0.371904 0.665980 0.489504 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3511(7) 0.6993(9) 0.3668(8) 0.047(3) Uani 1 1 d . . . . .
H12 H 0.339857 0.766205 0.369471 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3497(7) 0.6584(8) 0.2912(7) 0.036(3) Uani 1 1 d . . . . .
H13 H 0.338298 0.698706 0.243253 0.044 Uiso 1 1 calc R U . . .
C8 C 0.3939(7) 0.3897(8) 0.3496(7) 0.038(3) Uani 1 1 d . . . . .
H8A H 0.434207 0.364184 0.405446 0.046 Uiso 1 1 calc R U . . .
H8B H 0.337591 0.358099 0.334373 0.046 Uiso 1 1 calc R U . . .
C15 C 0.4093(9) 0.2595(7) 0.2612(9) 0.054(4) Uani 1 1 d . . . . .
H15A H 0.443002 0.220405 0.312212 0.064 Uiso 1 1 calc R U . . .
H15B H 0.347867 0.246084 0.245621 0.064 Uiso 1 1 calc R U . . .
C16 C 0.4312(9) 0.2272(9) 0.1892(9) 0.064(4) Uani 1 1 d . . . . .
H16A H 0.492799 0.239368 0.204267 0.077 Uiso 1 1 calc R U . . .
H16B H 0.420853 0.156787 0.179977 0.077 Uiso 1 1 calc R U . . .
C17 C 0.4036(10) 0.2535(12) 0.0439(9) 0.086(5) Uani 1 1 d . . . . .
H17A H 0.456159 0.287911 0.051048 0.128 Uiso 1 1 calc R U . . .
H17C H 0.357060 0.272383 -0.010205 0.128 Uiso 1 1 calc R U . . .
H17B H 0.413180 0.183577 0.043957 0.128 Uiso 1 1 calc R U . . .
C31 C 0.1546(8) 0.4527(8) 0.3982(8) 0.044(3) Uani 1 1 d . . . . .
C26 C 0.1499(9) 0.5108(10) 0.4626(8) 0.056(4) Uani 1 1 d . . . . .
C27 C 0.1584(10) 0.4670(11) 0.5428(9) 0.071(4) Uani 1 1 d . . . . .
H27 H 0.157120 0.506342 0.587313 0.085 Uiso 1 1 calc R U . . .
C28 C 0.1685(10) 0.3677(12) 0.5535(10) 0.082(5) Uani 1 1 d . . . . .
H28 H 0.172941 0.338896 0.605120 0.099 Uiso 1 1 calc R U . . .
C29 C 0.1721(10) 0.3094(10) 0.4883(10) 0.071(4) Uani 1 1 d . . . . .
H29 H 0.179339 0.241426 0.495602 0.085 Uiso 1 1 calc R U . . .
C30 C 0.1646(8) 0.3543(10) 0.4108(9) 0.054(4) Uani 1 1 d . . . . .
H30 H 0.166513 0.314860 0.366550 0.065 Uiso 1 1 calc R U . . .
C25 C 0.1400(9) 0.6201(10) 0.4511(8) 0.060(4) Uani 1 1 d . . . . .
H25A H 0.110205 0.645362 0.485409 0.072 Uiso 1 1 calc R U . . .
H25B H 0.197511 0.650305 0.472574 0.072 Uiso 1 1 calc R U . . .
C18 C 0.0040(7) 0.5372(8) 0.2004(8) 0.037(3) Uani 1 1 d . . . . .
C23 C -0.0449(7) 0.5841(8) 0.2381(8) 0.040(3) Uani 1 1 d . . . . .
C22 C -0.1340(9) 0.5927(11) 0.1896(11) 0.066(4) Uani 1 1 d . . . . .
H22 H -0.168400 0.622880 0.213894 0.079 Uiso 1 1 calc R U . . .
C21 C -0.1726(9) 0.5575(11) 0.1065(12) 0.076(5) Uani 1 1 d . . . . .
H21 H -0.232660 0.564224 0.075005 0.091 Uiso 1 1 calc R U . . .
C20 C -0.1227(9) 0.5118(11) 0.0687(10) 0.069(4) Uani 1 1 d . . . . .
H20 H -0.148821 0.487459 0.012270 0.083 Uiso 1 1 calc R U . . .
C19 C -0.0348(8) 0.5034(9) 0.1160(8) 0.050(3) Uani 1 1 d . . . . .
H19 H -0.000475 0.474443 0.091027 0.060 Uiso 1 1 calc R U . . .
C24 C -0.0035(7) 0.6194(9) 0.3320(8) 0.048(3) Uani 1 1 d . . . . .
H24A H -0.035935 0.675893 0.338331 0.057 Uiso 1 1 calc R U . . .
H24B H -0.007755 0.567239 0.369415 0.057 Uiso 1 1 calc R U . . .
C32 C 0.1007(10) 0.7545(9) 0.3493(9) 0.062(4) Uani 1 1 d . . . . .
H32B H 0.070848 0.790800 0.378495 0.075 Uiso 1 1 calc R U . . .
H32A H 0.162337 0.771251 0.377393 0.075 Uiso 1 1 calc R U . . .
C33 C 0.0664(10) 0.7871(9) 0.2583(10) 0.071(5) Uani 1 1 d . . . . .
H33B H 0.005233 0.768564 0.228530 0.086 Uiso 1 1 calc R U . . .
H33A H 0.070392 0.858400 0.255922 0.086 Uiso 1 1 calc R U . . .
C34 C 0.0803(15) 0.7596(13) 0.1286(12) 0.139(9) Uani 1 1 d . . . . .
H34A H 0.027148 0.722422 0.100743 0.209 Uiso 1 1 calc R U . . .
H34B H 0.121885 0.738877 0.106493 0.209 Uiso 1 1 calc R U . . .
H34C H 0.068026 0.828643 0.117011 0.209 Uiso 1 1 calc R U . . .
N1 N 0.4264(5) 0.3670(6) 0.2842(5) 0.031(2) Uani 1 1 d . . . . .
N2 N 0.0909(6) 0.6478(7) 0.3609(6) 0.044(3) Uani 1 1 d . . . . .
O1 O 0.3806(6) 0.2779(6) 0.1128(6) 0.055(2) Uani 1 1 d . . . . .
O2 O 0.1144(6) 0.7434(6) 0.2173(7) 0.072(3) 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 C1 2.250(10) . ?
BI1 C14 2.261(10) . ?
BI1 N1 2.510(8) . ?
BI1 BR1 2.8282(14) . ?
BI2 C18 2.252(11) . ?
BI2 C31 2.257(12) . ?
BI2 N2 2.504(9) . ?
BI2 BR2 2.8503(14) . ?
C1 C2 1.365(15) . ?
C1 C6 1.373(15) . ?
C6 C5 1.408(15) . ?
C6 C7 1.499(15) . ?
C5 C4 1.381(19) . ?
C5 H5 0.9300 . ?
C4 C3 1.340(19) . ?
C4 H4 0.9300 . ?
C3 C2 1.416(18) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 N1 1.467(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C9 1.349(13) . ?
C14 C13 1.397(13) . ?
C9 C10 1.431(15) . ?
C9 C8 1.501(14) . ?
C10 C11 1.351(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(16) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(15) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C8 N1 1.454(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 C16 1.477(16) . ?
C15 N1 1.503(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.398(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O1 1.408(14) . ?
C17 H17A 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17B 0.9600 . ?
C31 C30 1.349(15) . ?
C31 C26 1.372(16) . ?
C26 C27 1.432(18) . ?
C26 C25 1.493(17) . ?
C27 C28 1.357(18) . ?
C27 H27 0.9300 . ?
C28 C29 1.38(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.403(17) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C25 N2 1.452(15) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C18 C19 1.380(16) . ?
C18 C23 1.384(15) . ?
C23 C22 1.381(17) . ?
C23 C24 1.524(16) . ?
C22 C21 1.37(2) . ?
C22 H22 0.9300 . ?
C21 C20 1.39(2) . ?
C21 H21 0.9300 . ?
C20 C19 1.360(17) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C24 N2 1.501(14) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C32 C33 1.471(17) . ?
C32 N2 1.475(14) . ?
C32 H32B 0.9700 . ?
C32 H32A 0.9700 . ?
C33 O2 1.394(14) . ?
C33 H33B 0.9700 . ?
C33 H33A 0.9700 . ?
C34 O2 1.384(18) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 BI1 C14 98.3(4) . . ?
C1 BI1 N1 74.4(3) . . ?
C14 BI1 N1 71.2(3) . . ?
C1 BI1 BR1 90.8(3) . . ?
C14 BI1 BR1 92.8(3) . . ?
N1 BI1 BR1 155.86(19) . . ?
C18 BI2 C31 99.8(4) . . ?
C18 BI2 N2 75.2(4) . . ?
C31 BI2 N2 72.5(4) . . ?
C18 BI2 BR2 89.4(3) . . ?
C31 BI2 BR2 92.7(3) . . ?
N2 BI2 BR2 156.0(2) . . ?
C2 C1 C6 120.7(11) . . ?
C2 C1 BI1 122.8(9) . . ?
C6 C1 BI1 116.2(8) . . ?
C1 C6 C5 119.7(11) . . ?
C1 C6 C7 121.5(10) . . ?
C5 C6 C7 118.8(11) . . ?
C4 C5 C6 118.1(13) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C3 C4 C5 122.9(14) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C4 C3 C2 118.5(13) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C1 C2 C3 120.0(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N1 C7 C6 114.3(9) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C14 C13 119.7(10) . . ?
C9 C14 BI1 116.9(7) . . ?
C13 C14 BI1 123.2(8) . . ?
C14 C9 C10 118.5(10) . . ?
C14 C9 C8 121.0(10) . . ?
C10 C9 C8 120.0(10) . . ?
C11 C10 C9 121.3(11) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.2(11) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 118.8(11) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C14 121.4(11) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
N1 C8 C9 110.1(8) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C16 C15 N1 114.5(10) . . ?
C16 C15 H15A 108.6 . . ?
N1 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
N1 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
O1 C16 C15 110.7(11) . . ?
O1 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
C30 C31 C26 119.1(12) . . ?
C30 C31 BI2 125.7(10) . . ?
C26 C31 BI2 115.1(9) . . ?
C31 C26 C27 119.8(13) . . ?
C31 C26 C25 120.4(12) . . ?
C27 C26 C25 119.7(12) . . ?
C28 C27 C26 119.7(14) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.3(14) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C30 118.9(13) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C31 C30 C29 122.1(13) . . ?
C31 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
N2 C25 C26 112.1(10) . . ?
N2 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
N2 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C19 C18 C23 120.8(11) . . ?
C19 C18 BI2 123.2(9) . . ?
C23 C18 BI2 115.7(9) . . ?
C22 C23 C18 117.9(13) . . ?
C22 C23 C24 120.6(12) . . ?
C18 C23 C24 121.4(10) . . ?
C21 C22 C23 121.2(14) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C21 C20 120.6(13) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C19 C20 C21 118.6(14) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C19 C18 120.9(13) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
N2 C24 C23 112.6(9) . . ?
N2 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
N2 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C33 C32 N2 114.6(11) . . ?
C33 C32 H32B 108.6 . . ?
N2 C32 H32B 108.6 . . ?
C33 C32 H32A 108.6 . . ?
N2 C32 H32A 108.6 . . ?
H32B C32 H32A 107.6 . . ?
O2 C33 C32 109.7(12) . . ?
O2 C33 H33B 109.7 . . ?
C32 C33 H33B 109.7 . . ?
O2 C33 H33A 109.7 . . ?
C32 C33 H33A 109.7 . . ?
H33B C33 H33A 108.2 . . ?
O2 C34 H34A 109.5 . . ?
O2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C8 N1 C7 109.5(8) . . ?
C8 N1 C15 108.0(8) . . ?
C7 N1 C15 112.7(9) . . ?
C8 N1 BI1 105.9(6) . . ?
C7 N1 BI1 106.1(6) . . ?
C15 N1 BI1 114.3(7) . . ?
C25 N2 C32 110.2(10) . . ?
C25 N2 C24 109.8(9) . . ?
C32 N2 C24 111.6(10) . . ?
C25 N2 BI2 103.6(7) . . ?
C32 N2 BI2 115.7(7) . . ?
C24 N2 BI2 105.5(6) . . ?
C16 O1 C17 112.4(10) . . ?
C34 O2 C33 114.0(12) . . ?

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 0.6(17) . . . . ?
BI1 C1 C6 C5 174.4(8) . . . . ?
C2 C1 C6 C7 177.9(11) . . . . ?
BI1 C1 C6 C7 -8.2(14) . . . . ?
C1 C6 C5 C4 -0.9(18) . . . . ?
C7 C6 C5 C4 -178.4(12) . . . . ?
C6 C5 C4 C3 0(2) . . . . ?
C5 C4 C3 C2 2(2) . . . . ?
C6 C1 C2 C3 0.8(17) . . . . ?
BI1 C1 C2 C3 -172.6(9) . . . . ?
C4 C3 C2 C1 -2(2) . . . . ?
C1 C6 C7 N1 28.0(15) . . . . ?
C5 C6 C7 N1 -154.6(10) . . . . ?
C13 C14 C9 C10 3.3(15) . . . . ?
BI1 C14 C9 C10 -171.9(7) . . . . ?
C13 C14 C9 C8 174.8(9) . . . . ?
BI1 C14 C9 C8 -0.5(13) . . . . ?
C14 C9 C10 C11 -3.6(16) . . . . ?
C8 C9 C10 C11 -175.2(10) . . . . ?
C9 C10 C11 C12 2.6(18) . . . . ?
C10 C11 C12 C13 -1.3(18) . . . . ?
C11 C12 C13 C14 1.1(17) . . . . ?
C9 C14 C13 C12 -2.2(16) . . . . ?
BI1 C14 C13 C12 172.8(8) . . . . ?
C14 C9 C8 N1 30.9(14) . . . . ?
C10 C9 C8 N1 -157.8(9) . . . . ?
N1 C15 C16 O1 -61.6(15) . . . . ?
C30 C31 C26 C27 2(2) . . . . ?
BI2 C31 C26 C27 -175.7(10) . . . . ?
C30 C31 C26 C25 179.3(12) . . . . ?
BI2 C31 C26 C25 1.5(17) . . . . ?
C31 C26 C27 C28 -2(2) . . . . ?
C25 C26 C27 C28 -179.2(14) . . . . ?
C26 C27 C28 C29 1(2) . . . . ?
C27 C28 C29 C30 0(2) . . . . ?
C26 C31 C30 C29 -1(2) . . . . ?
BI2 C31 C30 C29 176.2(10) . . . . ?
C28 C29 C30 C31 1(2) . . . . ?
C31 C26 C25 N2 31.4(18) . . . . ?
C27 C26 C25 N2 -151.5(12) . . . . ?
C19 C18 C23 C22 2.3(16) . . . . ?
BI2 C18 C23 C22 176.1(8) . . . . ?
C19 C18 C23 C24 178.3(10) . . . . ?
BI2 C18 C23 C24 -7.8(13) . . . . ?
C18 C23 C22 C21 -1.1(18) . . . . ?
C24 C23 C22 C21 -177.2(12) . . . . ?
C23 C22 C21 C20 0(2) . . . . ?
C22 C21 C20 C19 0(2) . . . . ?
C21 C20 C19 C18 2(2) . . . . ?
C23 C18 C19 C20 -2.6(18) . . . . ?
BI2 C18 C19 C20 -175.9(9) . . . . ?
C22 C23 C24 N2 -153.8(10) . . . . ?
C18 C23 C24 N2 30.3(14) . . . . ?
N2 C32 C33 O2 -64.4(16) . . . . ?
C9 C8 N1 C7 73.7(11) . . . . ?
C9 C8 N1 C15 -163.2(9) . . . . ?
C9 C8 N1 BI1 -40.3(9) . . . . ?
C6 C7 N1 C8 -143.2(9) . . . . ?
C6 C7 N1 C15 96.5(11) . . . . ?
C6 C7 N1 BI1 -29.3(10) . . . . ?
C16 C15 N1 C8 174.5(11) . . . . ?
C16 C15 N1 C7 -64.4(14) . . . . ?
C16 C15 N1 BI1 56.9(13) . . . . ?
C26 C25 N2 C32 -166.3(11) . . . . ?
C26 C25 N2 C24 70.3(13) . . . . ?
C26 C25 N2 BI2 -42.0(12) . . . . ?
C33 C32 N2 C25 169.9(12) . . . . ?
C33 C32 N2 C24 -67.7(14) . . . . ?
C33 C32 N2 BI2 52.9(14) . . . . ?
C23 C24 N2 C25 -143.8(10) . . . . ?
C23 C24 N2 C32 93.6(11) . . . . ?
C23 C24 N2 BI2 -32.7(10) . . . . ?
C15 C16 O1 C17 176.3(11) . . . . ?
C32 C33 O2 C34 172.3(14) . . . . ?

_refine_diff_density_max         1.479
_refine_diff_density_min         -1.489
_refine_diff_density_rms         0.188

####################################################################### 
# 
# 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 1520815'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Bi I N O'
_chemical_formula_sum            'C17 H19 Bi I N O'
_chemical_formula_weight         589.21

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'
I I -0.4742 1.8119 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   14.942(2)
_cell_length_b                   13.8911(19)
_cell_length_c                   17.153(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.306(2)
_cell_angle_gamma                90
_cell_volume                     3522.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4853
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.222
_exptl_crystal_F_000             2176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    11.761
_shelx_estimated_absorpt_T_min   0.098
_shelx_estimated_absorpt_T_max   0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.080159
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;SADABS - V2.03 (Bruker 2001)was used for absorption 
correction. R(int) =  0.2272 before parameter refinement
 and 0.1156 after parameter refinement.  Ratio of minimum
 to maximum apparent transmission:  0.080159
 Lambda/2 correction factor = 0.0015
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16224
_diffrn_reflns_av_unetI/netI     0.1049
_diffrn_reflns_av_R_equivalents  0.1500
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             3109
_reflns_number_gt                2221
_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-2016/4 (Sheldrick, 2016)'
_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)+(0.0664P)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         3109
_refine_ls_number_parameters     190
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.980
_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 0.18611(4) 0.79168(4) 0.11999(3) 0.0318(2) Uani 1 1 d . . . . .
C14 C 0.3098(10) 0.7011(11) 0.0972(9) 0.039(4) Uani 1 1 d . . . . .
C9 C 0.3880(11) 0.7559(12) 0.0911(10) 0.043(4) Uani 1 1 d . . . . .
C10 C 0.4606(11) 0.7096(13) 0.0732(10) 0.051(5) Uani 1 1 d . . . . .
H10 H 0.513122 0.743892 0.068786 0.061 Uiso 1 1 calc R U . . .
C11 C 0.4588(11) 0.6115(13) 0.0610(10) 0.051(5) Uani 1 1 d . . . . .
H11 H 0.510410 0.580963 0.048791 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3850(11) 0.5591(12) 0.0664(10) 0.049(5) Uani 1 1 d . . . . .
H12 H 0.385729 0.492918 0.058288 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3084(10) 0.6030(10) 0.0839(9) 0.033(4) Uani 1 1 d . U . . .
H13 H 0.256306 0.567438 0.086859 0.040 Uiso 1 1 calc R U . . .
C8 C 0.3855(10) 0.8649(11) 0.0985(10) 0.042(4) Uani 1 1 d . . . . .
H8A H 0.446168 0.888435 0.116211 0.050 Uiso 1 1 calc R U . . .
H8B H 0.365011 0.892708 0.047207 0.050 Uiso 1 1 calc R U . . .
C1 C 0.2138(10) 0.7963(10) 0.2515(9) 0.033(4) Uani 1 1 d . . . . .
C6 C 0.2916(10) 0.8410(10) 0.2851(9) 0.033(4) Uani 1 1 d . . . . .
C5 C 0.3094(11) 0.8571(11) 0.3661(9) 0.042(4) Uani 1 1 d . . . . .
H5 H 0.363077 0.886254 0.388414 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2472(14) 0.8295(12) 0.4116(11) 0.057(5) Uani 1 1 d . . . . .
H4 H 0.258489 0.840105 0.465655 0.069 Uiso 1 1 calc R U . . .
C3 C 0.1650(13) 0.7845(11) 0.3785(10) 0.053(5) Uani 1 1 d . . . . .
H3 H 0.122255 0.766509 0.410149 0.063 Uiso 1 1 calc R U . . .
C2 C 0.1504(11) 0.7686(10) 0.2994(10) 0.040(4) Uani 1 1 d . . . . .
H2 H 0.097262 0.738573 0.276872 0.048 Uiso 1 1 calc R U . . .
C7 C 0.3615(10) 0.8694(11) 0.2340(10) 0.042(4) Uani 1 1 d . . . . .
H7A H 0.395835 0.923281 0.258678 0.050 Uiso 1 1 calc R U . . .
H7B H 0.403065 0.816017 0.232551 0.050 Uiso 1 1 calc R U . . .
C15 C 0.3094(11) 0.9999(10) 0.1441(11) 0.052(5) Uani 1 1 d . . . . .
H15A H 0.292040 1.013176 0.088502 0.062 Uiso 1 1 calc R U . . .
H15B H 0.365934 1.033305 0.160902 0.062 Uiso 1 1 calc R U . . .
C16 C 0.2386(13) 1.0415(12) 0.1881(14) 0.078(7) Uani 1 1 d . . . . .
H16A H 0.255064 1.030783 0.244259 0.094 Uiso 1 1 calc R U . . .
H16B H 0.233410 1.110322 0.178935 0.094 Uiso 1 1 calc R U . . .
C17 C 0.0955(13) 1.0084(15) 0.2180(12) 0.078(7) Uani 1 1 d . . . . .
H17A H 0.038945 0.977397 0.199556 0.116 Uiso 1 1 calc R U . . .
H17B H 0.121581 0.980333 0.267170 0.116 Uiso 1 1 calc R U . . .
H17C H 0.085313 1.075861 0.225316 0.116 Uiso 1 1 calc R U . . .
I I 0.06270(7) 0.61704(7) 0.12178(7) 0.0475(3) Uani 1 1 d . . . . .
N1 N 0.3260(8) 0.8959(9) 0.1536(8) 0.041(3) Uani 1 1 d . . . . .
O1 O 0.1559(7) 0.9961(7) 0.1611(7) 0.053(3) 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 C1 2.235(15) . ?
BI1 C14 2.315(14) . ?
BI1 N1 2.539(12) . ?
BI1 I 3.0500(12) . ?
C14 C13 1.381(19) . ?
C14 C9 1.41(2) . ?
C9 C10 1.34(2) . ?
C9 C8 1.52(2) . ?
C10 C11 1.38(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.34(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.37(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C8 N1 1.453(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C6 1.37(2) . ?
C1 C2 1.39(2) . ?
C6 C5 1.39(2) . ?
C6 C7 1.51(2) . ?
C5 C4 1.35(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.42(2) . ?
C4 H4 0.9300 . ?
C3 C2 1.36(2) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 N1 1.45(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C15 N1 1.471(17) . ?
C15 C16 1.50(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.405(19) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O1 1.43(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 BI1 C14 98.7(5) . . ?
C1 BI1 N1 74.2(5) . . ?
C14 BI1 N1 72.4(5) . . ?
C1 BI1 I 92.1(4) . . ?
C14 BI1 I 93.9(4) . . ?
N1 BI1 I 158.4(3) . . ?
C13 C14 C9 120.8(14) . . ?
C13 C14 BI1 124.8(11) . . ?
C9 C14 BI1 114.2(11) . . ?
C10 C9 C14 117.8(15) . . ?
C10 C9 C8 122.1(15) . . ?
C14 C9 C8 120.0(14) . . ?
C9 C10 C11 120.9(16) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 121.8(16) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.8(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 118.9(15) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
N1 C8 C9 112.0(12) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C6 C1 C2 119.0(14) . . ?
C6 C1 BI1 117.4(10) . . ?
C2 C1 BI1 123.0(12) . . ?
C1 C6 C5 121.4(14) . . ?
C1 C6 C7 119.4(14) . . ?
C5 C6 C7 119.2(14) . . ?
C4 C5 C6 118.7(16) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C4 C3 121.4(17) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C2 C3 C4 118.3(16) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C2 C1 121.2(16) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
N1 C7 C6 115.4(13) . . ?
N1 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
N1 C15 C16 116.3(14) . . ?
N1 C15 H15A 108.2 . . ?
C16 C15 H15A 108.2 . . ?
N1 C15 H15B 108.2 . . ?
C16 C15 H15B 108.2 . . ?
H15A C15 H15B 107.4 . . ?
O1 C16 C15 108.1(15) . . ?
O1 C16 H16A 110.1 . . ?
C15 C16 H16A 110.1 . . ?
O1 C16 H16B 110.1 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 N1 C8 111.6(12) . . ?
C7 N1 C15 112.7(13) . . ?
C8 N1 C15 109.2(12) . . ?
C7 N1 BI1 104.3(9) . . ?
C8 N1 BI1 104.2(8) . . ?
C15 N1 BI1 114.5(9) . . ?
C16 O1 C17 109.4(15) . . ?

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 -1(2) . . . . ?
BI1 C14 C9 C10 -176.0(13) . . . . ?
C13 C14 C9 C8 174.4(14) . . . . ?
BI1 C14 C9 C8 -0.7(19) . . . . ?
C14 C9 C10 C11 0(3) . . . . ?
C8 C9 C10 C11 -175.2(16) . . . . ?
C9 C10 C11 C12 0(3) . . . . ?
C10 C11 C12 C13 0(3) . . . . ?
C11 C12 C13 C14 -1(3) . . . . ?
C9 C14 C13 C12 1(2) . . . . ?
BI1 C14 C13 C12 176.0(11) . . . . ?
C10 C9 C8 N1 -151.1(16) . . . . ?
C14 C9 C8 N1 34(2) . . . . ?
C2 C1 C6 C5 2(2) . . . . ?
BI1 C1 C6 C5 172.6(11) . . . . ?
C2 C1 C6 C7 178.6(13) . . . . ?
BI1 C1 C6 C7 -10.3(18) . . . . ?
C1 C6 C5 C4 -1(2) . . . . ?
C7 C6 C5 C4 -178.5(14) . . . . ?
C6 C5 C4 C3 0(3) . . . . ?
C5 C4 C3 C2 1(3) . . . . ?
C4 C3 C2 C1 -1(2) . . . . ?
C6 C1 C2 C3 0(2) . . . . ?
BI1 C1 C2 C3 -171.0(12) . . . . ?
C1 C6 C7 N1 32(2) . . . . ?
C5 C6 C7 N1 -150.7(14) . . . . ?
N1 C15 C16 O1 -61(2) . . . . ?
C6 C7 N1 C8 -144.3(12) . . . . ?
C6 C7 N1 C15 92.4(15) . . . . ?
C6 C7 N1 BI1 -32.4(14) . . . . ?
C9 C8 N1 C7 68.2(16) . . . . ?
C9 C8 N1 C15 -166.6(14) . . . . ?
C9 C8 N1 BI1 -43.8(15) . . . . ?
C16 C15 N1 C7 -63.9(19) . . . . ?
C16 C15 N1 C8 171.4(15) . . . . ?
C16 C15 N1 BI1 55.1(19) . . . . ?
C15 C16 O1 C17 160.4(15) . . . . ?

_refine_diff_density_max         2.903
_refine_diff_density_min         -3.469
_refine_diff_density_rms         0.277

# start Validation Reply Form
_vrf_PLAT972_shelx               
;
PROBLEM: Check Calcd Residual Density  0.92A From     Bi1      -3.70 eA-3 
RESPONSE:
The highest unrefined electron density peaks (Q peaks) are located at:
Q1, 2.90 e A-3 from Bi1 ( 1.04 A)
Q2, 2.54 e A-3 from I1  ( 0.98 A) 
Q3,  2.35 e A-3 from Bi1  (0.97 A) 
Q4, 2.34 e A-3 from Bi1  (0.97 A) 
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.The observed 
electron density peaks
most likely correspond to the Q1, Q3, Q4 in the proximity of Bi1. 
;
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Residual Density  0.92A From     Bi1      -3.70 eA-3 
RESPONSE:
The highest unrefined electron density peaks (Q peaks) are located at:
Q1, 2.90 e A-3 from Bi1 ( 1.04 A)
Q2, 2.54 e A-3 from I1  ( 0.98 A) 
Q3,  2.35 e A-3 from Bi1  (0.97 A) 
Q4, 2.34 e A-3 from Bi1  (0.97 A) 
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.The observed 
electron density peaks
most likely correspond to the Q1, Q3, Q4 in the proximity of Bi1. 
;
# end Validation Reply Form

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1520816'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 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 Br N'
_chemical_formula_sum            'C22 H21 Bi Br N'
_chemical_formula_weight         588.29

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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   27.200(2)
_cell_length_b                   10.1132(9)
_cell_length_c                   19.7239(17)
_cell_angle_alpha                90
_cell_angle_beta                 132.9980(10)
_cell_angle_gamma                90
_cell_volume                     3968.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2773
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      20.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_F_000             2224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    10.904
_shelx_estimated_absorpt_T_min   0.100
_shelx_estimated_absorpt_T_max   0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.553326
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
; SADABS - V2.03 (Bruker 2001)was used for 
absorption  correction. R(int) =  0.1279 before parameter 
refinement and 0.0535 after parameter refinement.  Ratio of
 minimum to maximum apparent transmission:  0.553326
 Lambda/2 correction factor = 0.0015
;
_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            18397
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_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             3492
_reflns_number_gt                2678
_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-2016/4 (Sheldrick, 2016)'
_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)+(0.1153P)²+42.9671P] 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         3492
_refine_ls_number_parameters     226
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1896
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.093
_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 0.04201(3) 0.51413(5) 0.13126(4) 0.0500(3) Uani 1 1 d . . . . .
Br1 Br 0.07737(13) 0.7744(2) 0.17226(18) 0.1090(8) Uani 1 1 d . . . . .
C14 C 0.0883(7) 0.4674(14) 0.2746(9) 0.047(3) Uani 1 1 d . . . . .
C9 C 0.1113(6) 0.3383(13) 0.3069(8) 0.043(3) Uani 1 1 d . . . . .
C10 C 0.1400(9) 0.3072(19) 0.3952(11) 0.076(5) Uani 1 1 d . . . . .
H10 H 0.1555 0.2217 0.4172 0.091 Uiso 1 1 calc R U . . .
C11 C 0.1464(9) 0.401(2) 0.4521(11) 0.070(4) Uani 1 1 d . U . . .
H11 H 0.1681 0.3773 0.5125 0.084 Uiso 1 1 calc R U . . .
C12 C 0.1216(11) 0.527(2) 0.4222(13) 0.082(6) Uani 1 1 d . U . . .
H12 H 0.1240 0.5865 0.4601 0.099 Uiso 1 1 calc R U . . .
C13 C 0.0916(7) 0.5636(16) 0.3297(10) 0.053(3) Uani 1 1 d . . . . .
H13 H 0.0750 0.6485 0.3072 0.064 Uiso 1 1 calc R U . . .
C8 C 0.1082(7) 0.2400(13) 0.2468(11) 0.054(4) Uani 1 1 d . . . . .
H8A H 0.1513 0.2391 0.2645 0.065 Uiso 1 1 calc R U . . .
H8B H 0.1010 0.1527 0.2590 0.065 Uiso 1 1 calc R U . . .
C1 C 0.1313(7) 0.4630(13) 0.1506(9) 0.046(3) Uani 1 1 d . . . . .
C6 C 0.1338(6) 0.3297(13) 0.1311(8) 0.044(3) Uani 1 1 d . . . . .
C5 C 0.1868(7) 0.2939(16) 0.1400(9) 0.056(4) Uani 1 1 d . . . . .
H5 H 0.1890 0.2069 0.1270 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2353(7) 0.3769(19) 0.1664(11) 0.064(4) Uani 1 1 d . . . . .
H4 H 0.2710 0.3489 0.1733 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2300(10) 0.5054(16) 0.1829(13) 0.063(5) Uani 1 1 d . . . . .
H3 H 0.2626 0.5652 0.1992 0.075 Uiso 1 1 calc R U . . .
C2 C 0.1806(7) 0.5502(15) 0.1769(10) 0.051(3) Uani 1 1 d . . . . .
H2 H 0.1797 0.6379 0.1903 0.061 Uiso 1 1 calc R U . . .
C7 C 0.0800(7) 0.2365(14) 0.1019(9) 0.053(4) Uani 1 1 d . . . . .
H7A H 0.0424 0.2430 0.0354 0.064 Uiso 1 1 calc R U . . .
H7B H 0.0970 0.1467 0.1161 0.064 Uiso 1 1 calc R U . . .
C15 C -0.0104(7) 0.2170(14) 0.1023(12) 0.062(4) Uani 1 1 d . . . . .
H15A H -0.0426 0.2655 0.0447 0.074 Uiso 1 1 calc R U . . .
H15B H -0.0196 0.2378 0.1407 0.074 Uiso 1 1 calc R U . . .
C16 C -0.0225(8) 0.0737(15) 0.0806(14) 0.072(5) Uani 1 1 d . . . . .
H16A H -0.0183 0.0533 0.0367 0.087 Uiso 1 1 calc R U . . .
H16B H 0.0117 0.0239 0.1369 0.087 Uiso 1 1 calc R U . . .
C17 C -0.0898(8) 0.0316(14) 0.0413(12) 0.055(4) Uani 1 1 d . . . . .
C18 C -0.1475(9) 0.0694(16) -0.0438(12) 0.067(4) Uani 1 1 d . . . . .
H18 H -0.1454 0.1185 -0.0817 0.081 Uiso 1 1 calc R U . . .
C19 C -0.2116(10) 0.0347(19) -0.0761(15) 0.089(7) Uani 1 1 d . U . . .
H19 H -0.2512 0.0651 -0.1329 0.107 Uiso 1 1 calc R U . . .
C20 C -0.2126(10) -0.047(2) -0.0195(18) 0.083(6) Uani 1 1 d . U . . .
H20 H -0.2538 -0.0748 -0.0415 0.099 Uiso 1 1 calc R U . . .
C21 C -0.1577(10) -0.0845(17) 0.0629(15) 0.079(5) Uani 1 1 d . . . . .
H21 H -0.1597 -0.1379 0.0993 0.095 Uiso 1 1 calc R U . . .
C22 C -0.0959(9) -0.0431(17) 0.0951(13) 0.073(5) Uani 1 1 d . . . . .
H22 H -0.0570 -0.0661 0.1550 0.088 Uiso 1 1 calc R U . . .
N1 N 0.0566(6) 0.2655(13) 0.1489(8) 0.050(3) 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 2.225(13) . ?
Bi1 C1 2.247(14) . ?
Bi1 N1 2.532(13) . ?
Bi1 Br1 2.729(2) . ?
C14 C9 1.399(19) . ?
C14 C13 1.41(2) . ?
C9 C10 1.37(2) . ?
C9 C8 1.504(19) . ?
C10 C11 1.39(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.37(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.45(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C8 N1 1.438(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.38(2) . ?
C1 C6 1.416(18) . ?
C6 C5 1.376(18) . ?
C6 C7 1.488(18) . ?
C5 C4 1.33(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.37(2) . ?
C4 H4 0.9300 . ?
C3 C2 1.35(2) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 N1 1.469(16) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C15 N1 1.456(17) . ?
C15 C16 1.48(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.48(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.35(2) . ?
C17 C22 1.40(3) . ?
C18 C19 1.43(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.40(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.31(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.40(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 Bi1 C1 97.3(5) . . ?
C14 Bi1 N1 73.4(4) . . ?
C1 Bi1 N1 72.5(4) . . ?
C14 Bi1 Br1 92.8(4) . . ?
C1 Bi1 Br1 92.9(4) . . ?
N1 Bi1 Br1 157.9(3) . . ?
C9 C14 C13 121.2(13) . . ?
C9 C14 Bi1 117.8(9) . . ?
C13 C14 Bi1 121.0(11) . . ?
C10 C9 C14 118.7(14) . . ?
C10 C9 C8 121.7(14) . . ?
C14 C9 C8 119.4(11) . . ?
C9 C10 C11 121.4(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 122.1(16) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 118.0(15) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 118.4(15) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
N1 C8 C9 114.7(11) . . ?
N1 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C2 C1 C6 119.8(14) . . ?
C2 C1 Bi1 125.3(11) . . ?
C6 C1 Bi1 114.8(10) . . ?
C5 C6 C1 117.1(13) . . ?
C5 C6 C7 123.5(13) . . ?
C1 C6 C7 119.4(12) . . ?
C4 C5 C6 123.7(15) . . ?
C4 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
C5 C4 C3 117.0(15) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
C2 C3 C4 123.9(15) . . ?
C2 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
C3 C2 C1 118.4(15) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
N1 C7 C6 111.4(10) . . ?
N1 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N1 C15 C16 116.6(12) . . ?
N1 C15 H15A 108.1 . . ?
C16 C15 H15A 108.1 . . ?
N1 C15 H15B 108.1 . . ?
C16 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C17 C16 C15 112.6(13) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C22 117.0(15) . . ?
C18 C17 C16 122.7(16) . . ?
C22 C17 C16 120.1(16) . . ?
C17 C18 C19 120.8(18) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 117.9(19) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C21 C20 C19 122.4(19) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C20 C21 C22 118.6(19) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C21 C22 C17 123.1(17) . . ?
C21 C22 H22 118.5 . . ?
C17 C22 H22 118.5 . . ?
C8 N1 C15 116.3(12) . . ?
C8 N1 C7 111.4(11) . . ?
C15 N1 C7 115.3(11) . . ?
C8 N1 Bi1 106.3(8) . . ?
C15 N1 Bi1 103.7(8) . . ?
C7 N1 Bi1 101.9(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C14 C9 C10 -2.6(19) . . . . ?
Bi1 C14 C9 C10 -179.9(10) . . . . ?
C13 C14 C9 C8 -178.7(12) . . . . ?
Bi1 C14 C9 C8 4.0(16) . . . . ?
C14 C9 C10 C11 0(2) . . . . ?
C8 C9 C10 C11 176.1(14) . . . . ?
C9 C10 C11 C12 3(3) . . . . ?
C10 C11 C12 C13 -4(3) . . . . ?
C9 C14 C13 C12 2(2) . . . . ?
Bi1 C14 C13 C12 179.2(11) . . . . ?
C11 C12 C13 C14 1(2) . . . . ?
C10 C9 C8 N1 157.5(13) . . . . ?
C14 C9 C8 N1 -26.6(17) . . . . ?
C2 C1 C6 C5 0.1(18) . . . . ?
Bi1 C1 C6 C5 178.7(9) . . . . ?
C2 C1 C6 C7 -179.5(12) . . . . ?
Bi1 C1 C6 C7 -0.9(15) . . . . ?
C1 C6 C5 C4 1(2) . . . . ?
C7 C6 C5 C4 -179.8(13) . . . . ?
C6 C5 C4 C3 -2(2) . . . . ?
C5 C4 C3 C2 2(3) . . . . ?
C4 C3 C2 C1 -2(2) . . . . ?
C6 C1 C2 C3 0(2) . . . . ?
Bi1 C1 C2 C3 -178.1(11) . . . . ?
C5 C6 C7 N1 145.2(12) . . . . ?
C1 C6 C7 N1 -35.3(17) . . . . ?
N1 C15 C16 C17 174.6(14) . . . . ?
C15 C16 C17 C18 68(2) . . . . ?
C15 C16 C17 C22 -107.0(18) . . . . ?
C22 C17 C18 C19 0(2) . . . . ?
C16 C17 C18 C19 -175.1(14) . . . . ?
C17 C18 C19 C20 -4(2) . . . . ?
C18 C19 C20 C21 4(3) . . . . ?
C19 C20 C21 C22 -1(3) . . . . ?
C20 C21 C22 C17 -3(3) . . . . ?
C18 C17 C22 C21 3(2) . . . . ?
C16 C17 C22 C21 179.1(15) . . . . ?
C9 C8 N1 C15 -83.6(14) . . . . ?
C9 C8 N1 C7 141.4(12) . . . . ?
C9 C8 N1 Bi1 31.2(12) . . . . ?
C16 C15 N1 C8 -78.0(18) . . . . ?
C16 C15 N1 C7 55(2) . . . . ?
C16 C15 N1 Bi1 165.7(13) . . . . ?
C6 C7 N1 C8 -66.8(15) . . . . ?
C6 C7 N1 C15 157.8(12) . . . . ?
C6 C7 N1 Bi1 46.2(12) . . . . ?

_refine_diff_density_max         6.058
_refine_diff_density_min         -2.388
_refine_diff_density_rms         0.231

# start Validation Reply Form
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Residual Density  0.78A From     Bi1       6.23 eA-3
RESPONSE:
The highest unrefined electron density peaks (Q peaks) are located at:
Q1, 6.06 e A-3 from Bi1 ( 0.817 A)
Q2, 1.15 e A-3 from Br1  ( 1.069 A) 
Q3,  1.11 e A-3 from C13  (0.58 A) 
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.
The observed electron density peaks
most likely correspond to the Q1 in the proximity of Bi1. 
;
_vrf_PLAT973_shelx               
;
PROBLEM:  Check Calcd Positive Residual Density on     Bi1       3.42 eA-3  
RESPONSE:
The highest unrefined electron density peaks (Q peaks) are located at:
Q1, 6.06 e A-3 from Bi1 ( 0.817 A)
Q2, 1.15 e A-3 from Br1  ( 1.069 A) 
Q3,  1.11 e A-3 from C13  (0.58 A) 
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.
The observed electron density peaks
most likely correspond to the Q1 in the proximity of Bi1. 
;
# end Validation Reply Form


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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1520817'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 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 Cl N'
_chemical_formula_sum            'C22 H21 Bi Cl N'
_chemical_formula_weight         543.83

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'
Cl Cl 0.1484 0.1585 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   27.197(3)
_cell_length_b                   10.0324(11)
_cell_length_c                   19.709(3)
_cell_angle_alpha                90
_cell_angle_beta                 132.929(4)
_cell_angle_gamma                90
_cell_volume                     3937.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5969
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_F_000             2080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    9.095
_shelx_estimated_absorpt_T_min   0.122
_shelx_estimated_absorpt_T_max   0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.249417
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;SADABS - V2.03 (Bruker 2001)was used for 
absorption correction. R(int) 0.2080 before parameter refinement and 0.0703 
after parameter refinement.  Ratio of minimum to maximum apparent
 transmission:  0.249417 Lambda/2 correction factor = 0.0015
;
_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            18798
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.070
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3655
_reflns_number_gt                2739
_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-2016/4 (Sheldrick, 2016)'
_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)+(0.0422P)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         3655
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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 0.45735(2) 0.52103(3) 0.86941(2) 0.04335(15) Uani 1 1 d . . . . .
C1 C 0.3688(4) 0.4658(8) 0.8505(5) 0.0384(19) Uani 1 1 d . . . . .
C6 C 0.3650(4) 0.3362(8) 0.8689(5) 0.0402(19) Uani 1 1 d . . . . .
C5 C 0.3128(4) 0.2942(9) 0.8594(6) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.3102 0.2060 0.8712 0.063 Uiso 1 1 calc R U . . .
C4 C 0.2641(5) 0.3844(11) 0.8322(6) 0.060(3) Uani 1 1 d . . . . .
H4 H 0.2287 0.3564 0.8262 0.072 Uiso 1 1 calc R U . . .
C3 C 0.2666(5) 0.5115(10) 0.8142(7) 0.059(3) Uani 1 1 d . . . . .
H3 H 0.2331 0.5705 0.7961 0.071 Uiso 1 1 calc R U . . .
C2 C 0.3177(4) 0.5556(9) 0.8221(5) 0.048(2) Uani 1 1 d . . . . .
H2 H 0.3189 0.6440 0.8090 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4188(4) 0.2398(8) 0.8993(5) 0.045(2) Uani 1 1 d . . . . .
H7A H 0.4010 0.1497 0.8826 0.053 Uiso 1 1 calc R U . . .
H7B H 0.4557 0.2439 0.9660 0.053 Uiso 1 1 calc R U . . .
C8 C 0.3911(4) 0.2448(8) 0.7510(5) 0.045(2) Uani 1 1 d . . . . .
H8A H 0.3476 0.2417 0.7320 0.054 Uiso 1 1 calc R U . . .
H8B H 0.4000 0.1575 0.7400 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3896(4) 0.3458(9) 0.6941(5) 0.044(2) Uani 1 1 d . . . . .
C10 C 0.3626(4) 0.3153(10) 0.6058(6) 0.060(3) Uani 1 1 d . . . . .
H10 H 0.3483 0.2285 0.5840 0.072 Uiso 1 1 calc R U . . .
C11 C 0.3562(5) 0.4073(12) 0.5502(6) 0.066(3) Uani 1 1 d . . . . .
H11 H 0.3365 0.3837 0.4907 0.079 Uiso 1 1 calc R U . . .
C12 C 0.3783(5) 0.5344(12) 0.5806(8) 0.076(4) Uani 1 1 d . . . . .
H12 H 0.3745 0.5968 0.5423 0.091 Uiso 1 1 calc R U . . .
C13 C 0.4071(4) 0.5709(10) 0.6703(6) 0.058(2) Uani 1 1 d . . . . .
H13 H 0.4234 0.6567 0.6925 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4106(4) 0.4749(8) 0.7251(5) 0.0402(19) Uani 1 1 d . . . . .
C15 C 0.5119(4) 0.2184(8) 0.8999(6) 0.050(2) Uani 1 1 d . . . . .
H15A H 0.5216 0.2368 0.8617 0.060 Uiso 1 1 calc R U . . .
H15B H 0.5450 0.2656 0.9579 0.060 Uiso 1 1 calc R U . . .
C16 C 0.5211(4) 0.0739(9) 0.9201(7) 0.065(3) Uani 1 1 d . . . . .
H16A H 0.4859 0.0245 0.8641 0.078 Uiso 1 1 calc R U . . .
H16B H 0.5183 0.0547 0.9656 0.078 Uiso 1 1 calc R U . . .
C17 C 0.5888(4) 0.0315(8) 0.9569(6) 0.048(2) Uani 1 1 d . . . . .
C18 C 0.6459(5) 0.0694(9) 1.0423(6) 0.059(2) Uani 1 1 d . . . . .
H18 H 0.6427 0.1170 1.0796 0.070 Uiso 1 1 calc R U . . .
C19 C 0.7095(6) 0.0398(11) 1.0764(8) 0.083(4) Uani 1 1 d . . . . .
H19 H 0.7481 0.0715 1.1337 0.100 Uiso 1 1 calc R U . . .
C20 C 0.7130(6) -0.0388(12) 1.0220(11) 0.090(4) Uani 1 1 d . . . . .
H20 H 0.7548 -0.0641 1.0447 0.108 Uiso 1 1 calc R U . . .
C21 C 0.6574(6) -0.0791(10) 0.9372(9) 0.080(3) Uani 1 1 d . . . . .
H21 H 0.6605 -0.1305 0.9010 0.096 Uiso 1 1 calc R U . . .
C22 C 0.5954(5) -0.0426(9) 0.9048(8) 0.069(3) Uani 1 1 d . . . . .
H22 H 0.5569 -0.0691 0.8456 0.083 Uiso 1 1 calc R U . . .
Cl1 Cl 0.42197(13) 0.7734(2) 0.82959(19) 0.0726(7) Uani 1 1 d . . . . .
N1 N 0.4435(3) 0.2759(7) 0.8518(4) 0.0429(17) 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 2.235(8) . ?
Bi1 C1 2.240(7) . ?
Bi1 N1 2.476(7) . ?
Bi1 Cl1 2.632(2) . ?
C1 C6 1.373(10) . ?
C1 C2 1.414(11) . ?
C6 C5 1.366(10) . ?
C6 C7 1.497(10) . ?
C5 C4 1.376(12) . ?
C5 H5 0.9300 . ?
C4 C3 1.338(12) . ?
C4 H4 0.9300 . ?
C3 C2 1.362(12) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 N1 1.523(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.490(9) . ?
C8 C9 1.491(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.379(11) . ?
C9 C10 1.386(10) . ?
C10 C11 1.350(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.410(14) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(11) . ?
C13 H13 0.9300 . ?
C15 C16 1.479(11) . ?
C15 N1 1.512(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.509(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.352(12) . ?
C17 C22 1.376(13) . ?
C18 C19 1.394(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.341(16) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(13) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 Bi1 C1 97.0(3) . . ?
C14 Bi1 N1 73.5(2) . . ?
C1 Bi1 N1 71.8(2) . . ?
C14 Bi1 Cl1 92.5(2) . . ?
C1 Bi1 Cl1 93.2(2) . . ?
N1 Bi1 Cl1 157.54(16) . . ?
C6 C1 C2 118.5(7) . . ?
C6 C1 Bi1 117.2(6) . . ?
C2 C1 Bi1 124.4(6) . . ?
C5 C6 C1 121.0(8) . . ?
C5 C6 C7 119.8(8) . . ?
C1 C6 C7 119.3(7) . . ?
C6 C5 C4 119.1(9) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C3 C4 C5 121.4(9) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C3 C2 120.8(9) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C2 C1 119.4(8) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C6 C7 N1 108.7(6) . . ?
C6 C7 H7A 109.9 . . ?
N1 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
N1 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N1 C8 C9 111.8(7) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.0(8) . . ?
C14 C9 C8 120.9(7) . . ?
C10 C9 C8 120.9(8) . . ?
C11 C10 C9 122.2(10) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 120.7(9) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.7(8) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 118.4(9) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C9 C14 C13 120.9(8) . . ?
C9 C14 Bi1 117.6(5) . . ?
C13 C14 Bi1 121.3(7) . . ?
C16 C15 N1 117.0(6) . . ?
C16 C15 H15A 108.1 . . ?
N1 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
N1 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C15 C16 C17 109.4(7) . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C22 117.2(8) . . ?
C18 C17 C16 120.7(9) . . ?
C22 C17 C16 122.1(9) . . ?
C17 C18 C19 122.5(10) . . ?
C17 C18 H18 118.7 . . ?
C19 C18 H18 118.7 . . ?
C20 C19 C18 117.6(11) . . ?
C20 C19 H19 121.2 . . ?
C18 C19 H19 121.2 . . ?
C21 C20 C19 121.5(11) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 118.7(11) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C17 C22 C21 122.4(10) . . ?
C17 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C8 N1 C15 114.0(6) . . ?
C8 N1 C7 110.3(6) . . ?
C15 N1 C7 113.2(6) . . ?
C8 N1 Bi1 108.1(4) . . ?
C15 N1 Bi1 106.7(4) . . ?
C7 N1 Bi1 103.8(4) . . ?

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 0.5(11) . . . . ?
Bi1 C1 C6 C5 179.8(6) . . . . ?
C2 C1 C6 C7 -179.8(6) . . . . ?
Bi1 C1 C6 C7 -0.6(9) . . . . ?
C1 C6 C5 C4 -0.9(12) . . . . ?
C7 C6 C5 C4 179.5(7) . . . . ?
C6 C5 C4 C3 0.5(13) . . . . ?
C5 C4 C3 C2 0.2(14) . . . . ?
C4 C3 C2 C1 -0.6(13) . . . . ?
C6 C1 C2 C3 0.2(11) . . . . ?
Bi1 C1 C2 C3 -179.0(6) . . . . ?
C5 C6 C7 N1 146.2(7) . . . . ?
C1 C6 C7 N1 -33.4(9) . . . . ?
N1 C8 C9 C14 -26.8(10) . . . . ?
N1 C8 C9 C10 157.9(7) . . . . ?
C14 C9 C10 C11 -0.2(12) . . . . ?
C8 C9 C10 C11 175.2(8) . . . . ?
C9 C10 C11 C12 2.0(14) . . . . ?
C10 C11 C12 C13 -1.1(14) . . . . ?
C11 C12 C13 C14 -1.4(14) . . . . ?
C10 C9 C14 C13 -2.4(12) . . . . ?
C8 C9 C14 C13 -177.9(7) . . . . ?
C10 C9 C14 Bi1 -177.9(6) . . . . ?
C8 C9 C14 Bi1 6.6(10) . . . . ?
C12 C13 C14 C9 3.3(12) . . . . ?
C12 C13 C14 Bi1 178.6(6) . . . . ?
N1 C15 C16 C17 173.0(7) . . . . ?
C15 C16 C17 C18 70.6(11) . . . . ?
C15 C16 C17 C22 -107.2(10) . . . . ?
C22 C17 C18 C19 2.1(14) . . . . ?
C16 C17 C18 C19 -175.7(8) . . . . ?
C17 C18 C19 C20 -4.2(15) . . . . ?
C18 C19 C20 C21 3.6(17) . . . . ?
C19 C20 C21 C22 -1.1(18) . . . . ?
C18 C17 C22 C21 0.6(14) . . . . ?
C16 C17 C22 C21 178.4(9) . . . . ?
C20 C21 C22 C17 -1.1(17) . . . . ?
C9 C8 N1 C15 -88.1(8) . . . . ?
C9 C8 N1 C7 143.2(6) . . . . ?
C9 C8 N1 Bi1 30.3(7) . . . . ?
C16 C15 N1 C8 -75.9(9) . . . . ?
C16 C15 N1 C7 51.2(10) . . . . ?
C16 C15 N1 Bi1 164.8(7) . . . . ?
C6 C7 N1 C8 -70.6(8) . . . . ?
C6 C7 N1 C15 160.4(6) . . . . ?
C6 C7 N1 Bi1 45.1(6) . . . . ?

_refine_diff_density_max         2.513
_refine_diff_density_min         -1.516
_refine_diff_density_rms         0.151

####################################################################### 
# 
# 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 1520818'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013/4
_shelx_SHELXL_version_number     2013/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 Bi Br N'
_chemical_formula_sum            'C21 H19 Bi Br N'
_chemical_formula_weight         574.26

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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   7.5186(5)
_cell_length_b                   10.6718(7)
_cell_length_c                   22.4700(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.532(7)
_cell_angle_gamma                90
_cell_volume                     1797.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    2796
_cell_measurement_theta_min      4.1690
_cell_measurement_theta_max      28.7120

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    12.034
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.61746
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8333
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.149
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3525
_reflns_number_gt                3090
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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)+(0.0270P)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         3525
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C14 C 0.3908(6) 0.5915(5) 1.1032(2) 0.0117(12) Uani 1 1 d . . . . .
C13 C 0.2586(7) 0.5006(5) 1.0938(3) 0.0151(12) Uani 1 1 d . . . . .
H13 H 0.2101 0.4833 1.0553 0.018 Uiso 1 1 calc R U . . .
C12 C 0.1990(7) 0.4352(5) 1.1424(3) 0.0143(12) Uani 1 1 d . . . . .
H12 H 0.1103 0.3748 1.1362 0.017 Uiso 1 1 calc R U . . .
C11 C 0.2706(7) 0.4598(5) 1.1990(3) 0.0165(13) Uani 1 1 d . . . . .
H11 H 0.2317 0.4153 1.2311 0.020 Uiso 1 1 calc R U . . .
C10 C 0.4014(7) 0.5513(5) 1.2088(3) 0.0152(13) Uani 1 1 d . . . . .
H10 H 0.4498 0.5677 1.2474 0.018 Uiso 1 1 calc R U . . .
C9 C 0.4600(6) 0.6185(5) 1.1610(2) 0.0100(11) Uani 1 1 d . . . . .
C8 C 0.5820(7) 0.7296(5) 1.1726(2) 0.0124(12) Uani 1 1 d . . . . .
H8A H 0.5103 0.8036 1.1783 0.015 Uiso 1 1 calc R U . . .
H8B H 0.6565 0.7154 1.2092 0.015 Uiso 1 1 calc R U . . .
C1 C 0.4269(7) 0.8836(5) 1.0543(3) 0.0164(13) Uani 1 1 d . . . . .
C2 C 0.2672(7) 0.9403(6) 1.0340(3) 0.0211(14) Uani 1 1 d . . . . .
H2 H 0.1877 0.8984 1.0072 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2252(8) 1.0610(6) 1.0540(3) 0.0237(15) Uani 1 1 d . . . . .
H3 H 0.1168 1.0980 1.0412 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3453(8) 1.1240(6) 1.0927(3) 0.0216(14) Uani 1 1 d . . . . .
H4 H 0.3187 1.2041 1.1057 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5067(7) 1.0677(5) 1.1123(3) 0.0191(13) Uani 1 1 d . . . . .
H5 H 0.5878 1.1108 1.1381 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5472(7) 0.9489(5) 1.0937(2) 0.0134(12) Uani 1 1 d . . . . .
C7 C 0.7232(7) 0.8885(5) 1.1146(3) 0.0149(13) Uani 1 1 d . . . . .
H7A H 0.8088 0.9018 1.0851 0.018 Uiso 1 1 calc R U . . .
H7B H 0.7700 0.9267 1.1517 0.018 Uiso 1 1 calc R U . . .
C15 C 0.8702(7) 0.6824(5) 1.1320(3) 0.0157(13) Uani 1 1 d . . . . .
H15A H 0.9328 0.6906 1.0960 0.019 Uiso 1 1 calc R U . . .
H15B H 0.8441 0.5942 1.1371 0.019 Uiso 1 1 calc R U . . .
C16 C 0.9915(7) 0.7258(5) 1.1845(3) 0.0114(12) Uani 1 1 d . . . . .
C21 C 0.9836(7) 0.6711(5) 1.2402(3) 0.0177(13) Uani 1 1 d . . . . .
H21 H 0.9077 0.6034 1.2445 0.021 Uiso 1 1 calc R U . . .
C20 C 1.0868(8) 0.7156(6) 1.2896(3) 0.0202(14) Uani 1 1 d . . . . .
H20 H 1.0778 0.6788 1.3268 0.024 Uiso 1 1 calc R U . . .
C19 C 1.2027(7) 0.8142(5) 1.2839(3) 0.0219(15) Uani 1 1 d . . . . .
H19 H 1.2716 0.8444 1.3170 0.026 Uiso 1 1 calc R U . . .
C18 C 1.2153(7) 0.8680(6) 1.2280(3) 0.0199(14) Uani 1 1 d . . . . .
H18 H 1.2940 0.9339 1.2234 0.024 Uiso 1 1 calc R U . . .
C17 C 1.1103(7) 0.8232(5) 1.1793(3) 0.0177(13) Uani 1 1 d . . . . .
H17 H 1.1198 0.8596 1.1421 0.021 Uiso 1 1 calc R U . . .
N1 N 0.6976(5) 0.7530(4) 1.1235(2) 0.0118(10) Uani 1 1 d . . . . .
Bi1 Bi 0.51298(3) 0.69031(2) 1.02908(2) 0.01437(8) Uani 1 1 d . . . . .
Br1 Br 0.20958(9) 0.65383(6) 0.95321(3) 0.03012(17) 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 C9 1.391(7) . ?
C14 C13 1.393(7) . ?
C14 Bi1 2.229(5) . ?
C13 C12 1.400(8) . ?
C13 H13 0.9300 . ?
C12 C11 1.366(8) . ?
C12 H12 0.9300 . ?
C11 C10 1.391(8) . ?
C11 H11 0.9300 . ?
C10 C9 1.393(8) . ?
C10 H10 0.9300 . ?
C9 C8 1.510(7) . ?
C8 N1 1.479(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.389(7) . ?
C1 C6 1.399(7) . ?
C1 Bi1 2.248(6) . ?
C2 C3 1.408(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(7) . ?
C7 N1 1.475(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C15 N1 1.500(7) . ?
C15 C16 1.506(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.381(7) . ?
C16 C21 1.386(8) . ?
C21 C20 1.388(8) . ?
C21 H21 0.9300 . ?
C20 C19 1.378(8) . ?
C20 H20 0.9300 . ?
C19 C18 1.391(9) . ?
C19 H19 0.9300 . ?
C18 C17 1.382(8) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
N1 Bi1 2.531(4) . ?
Bi1 Br1 2.7653(7) . ?

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
C9 C14 C13 119.7(5) . . ?
C9 C14 Bi1 117.0(4) . . ?
C13 C14 Bi1 123.2(4) . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C10 C9 120.1(5) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C14 C9 C10 119.8(5) . . ?
C14 C9 C8 120.1(5) . . ?
C10 C9 C8 119.7(5) . . ?
N1 C8 C9 112.8(4) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C2 C1 C6 119.3(5) . . ?
C2 C1 Bi1 125.1(4) . . ?
C6 C1 Bi1 115.6(4) . . ?
C1 C2 C3 120.2(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.2(5) . . ?
C5 C6 C7 120.5(5) . . ?
C1 C6 C7 119.3(5) . . ?
N1 C7 C6 109.8(4) . . ?
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 . . ?
N1 C15 C16 114.2(4) . . ?
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 C21 117.8(5) . . ?
C17 C16 C15 121.4(5) . . ?
C21 C16 C15 120.7(5) . . ?
C16 C21 C20 121.1(6) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C19 C20 C21 120.3(6) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C19 C18 119.2(5) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C17 C18 C19 119.7(6) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C16 C17 C18 121.8(6) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C7 N1 C8 110.9(4) . . ?
C7 N1 C15 112.9(4) . . ?
C8 N1 C15 112.0(4) . . ?
C7 N1 Bi1 102.4(3) . . ?
C8 N1 Bi1 105.4(3) . . ?
C15 N1 Bi1 112.7(3) . . ?
C14 Bi1 C1 95.8(2) . . ?
C14 Bi1 N1 74.34(17) . . ?
C1 Bi1 N1 72.28(17) . . ?
C14 Bi1 Br1 91.45(13) . . ?
C1 Bi1 Br1 92.59(14) . . ?
N1 Bi1 Br1 157.64(10) . . ?

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 -1.3(8) . . . . ?
Bi1 C14 C13 C12 174.7(4) . . . . ?
C14 C13 C12 C11 -0.3(8) . . . . ?
C13 C12 C11 C10 0.9(8) . . . . ?
C12 C11 C10 C9 0.1(7) . . . . ?
C13 C14 C9 C10 2.3(7) . . . . ?
Bi1 C14 C9 C10 -173.9(4) . . . . ?
C13 C14 C9 C8 -170.6(5) . . . . ?
Bi1 C14 C9 C8 13.1(6) . . . . ?
C11 C10 C9 C14 -1.7(7) . . . . ?
C11 C10 C9 C8 171.3(4) . . . . ?
C14 C9 C8 N1 -34.3(6) . . . . ?
C10 C9 C8 N1 152.7(5) . . . . ?
C6 C1 C2 C3 -1.5(9) . . . . ?
Bi1 C1 C2 C3 178.4(4) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C3 C4 C5 C6 -0.5(9) . . . . ?
C4 C5 C6 C1 0.6(9) . . . . ?
C4 C5 C6 C7 179.4(5) . . . . ?
C2 C1 C6 C5 0.4(9) . . . . ?
Bi1 C1 C6 C5 -179.6(4) . . . . ?
C2 C1 C6 C7 -178.5(5) . . . . ?
Bi1 C1 C6 C7 1.6(7) . . . . ?
C5 C6 C7 N1 144.0(5) . . . . ?
C1 C6 C7 N1 -37.2(7) . . . . ?
N1 C15 C16 C17 -86.8(6) . . . . ?
N1 C15 C16 C21 91.3(6) . . . . ?
C17 C16 C21 C20 2.3(8) . . . . ?
C15 C16 C21 C20 -175.9(5) . . . . ?
C16 C21 C20 C19 -1.3(8) . . . . ?
C21 C20 C19 C18 -0.3(8) . . . . ?
C20 C19 C18 C17 0.8(8) . . . . ?
C21 C16 C17 C18 -1.7(8) . . . . ?
C15 C16 C17 C18 176.5(5) . . . . ?
C19 C18 C17 C16 0.2(8) . . . . ?
C6 C7 N1 C8 -65.2(5) . . . . ?
C6 C7 N1 C15 168.3(5) . . . . ?
C6 C7 N1 Bi1 46.9(5) . . . . ?
C9 C8 N1 C7 143.6(4) . . . . ?
C9 C8 N1 C15 -89.3(5) . . . . ?
C9 C8 N1 Bi1 33.5(5) . . . . ?
C16 C15 N1 C7 59.1(6) . . . . ?
C16 C15 N1 C8 -66.9(6) . . . . ?
C16 C15 N1 Bi1 174.4(4) . . . . ?

_refine_diff_density_max         1.668
_refine_diff_density_min         -1.397
_refine_diff_density_rms         0.183

####################################################################### 
# 
# 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 1520819'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 Bi I N'
_chemical_formula_sum            'C21 H19 Bi I N'
_chemical_formula_weight         621.25

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'
I I -0.4742 1.8119 '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      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                   7.3565(2)
_cell_length_b                   10.8639(4)
_cell_length_c                   23.1182(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.701(3)
_cell_angle_gamma                90
_cell_volume                     1845.56(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    2814
_cell_measurement_theta_min      3.7200
_cell_measurement_theta_max      28.1480

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.236
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    11.228
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.40147
_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            6828
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3243
_reflns_number_gt                2958
_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)+(0.0162P)²+0.4703P] 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         3243
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4321(6) 0.3868(5) 0.5560(2) 0.0137(11) Uani 1 1 d . . . . .
C2 C 0.2685(6) 0.4407(5) 0.5367(2) 0.0170(12) Uani 1 1 d . . . . .
H2 H 0.1881 0.3972 0.5122 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2251(7) 0.5588(6) 0.5539(2) 0.0219(13) Uani 1 1 d . . . . .
H3 H 0.1159 0.5944 0.5407 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3441(7) 0.6244(5) 0.5910(2) 0.0211(13) Uani 1 1 d . . . . .
H4 H 0.3140 0.7030 0.6032 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5072(7) 0.5714(5) 0.6093(2) 0.0188(12) Uani 1 1 d . . . . .
H5 H 0.5882 0.6159 0.6333 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5530(6) 0.4530(5) 0.5927(2) 0.0139(11) Uani 1 1 d . . . . .
C7 C 0.7317(6) 0.3967(5) 0.6126(2) 0.0152(12) Uani 1 1 d . . . . .
H7A H 0.8202 0.4087 0.5833 0.018 Uiso 1 1 calc R U . . .
H7B H 0.7772 0.4367 0.6479 0.018 Uiso 1 1 calc R U . . .
C8 C 0.5863(6) 0.2428(5) 0.6715(2) 0.0127(11) Uani 1 1 d . . . . .
H8A H 0.5088 0.3142 0.6755 0.015 Uiso 1 1 calc R U . . .
H8B H 0.6598 0.2337 0.7072 0.015 Uiso 1 1 calc R U . . .
C9 C 0.4684(6) 0.1297(5) 0.6625(2) 0.0114(11) Uani 1 1 d . . . . .
C10 C 0.4110(6) 0.0644(5) 0.7101(2) 0.0137(11) Uani 1 1 d . . . . .
H10 H 0.4565 0.0848 0.7471 0.016 Uiso 1 1 calc R U . . .
C11 C 0.2882(6) -0.0296(5) 0.7030(2) 0.0173(12) Uani 1 1 d . . . . .
H11 H 0.2499 -0.0722 0.7351 0.021 Uiso 1 1 calc R U . . .
C12 C 0.2212(6) -0.0610(5) 0.6485(2) 0.0163(12) Uani 1 1 d . . . . .
H12 H 0.1378 -0.1250 0.6438 0.020 Uiso 1 1 calc R U . . .
C13 C 0.2779(6) 0.0026(5) 0.6004(2) 0.0132(11) Uani 1 1 d . . . . .
H13 H 0.2317 -0.0184 0.5636 0.016 Uiso 1 1 calc R U . . .
C14 C 0.4030(6) 0.0974(5) 0.6072(2) 0.0103(11) Uani 1 1 d . . . . .
C15 C 0.8850(6) 0.1967(5) 0.6318(2) 0.0180(12) Uani 1 1 d . . . . .
H15A H 0.9549 0.2083 0.5977 0.022 Uiso 1 1 calc R U . . .
H15B H 0.8601 0.1094 0.6352 0.022 Uiso 1 1 calc R U . . .
C16 C 0.9981(6) 0.2373(5) 0.6841(2) 0.0130(11) Uani 1 1 d . . . . .
C17 C 1.1168(6) 0.3373(5) 0.6807(2) 0.0145(12) Uani 1 1 d . . . . .
H17 H 1.1298 0.3766 0.6454 0.017 Uiso 1 1 calc R U . . .
C18 C 1.2144(6) 0.3779(5) 0.7291(2) 0.0217(13) Uani 1 1 d . . . . .
H18 H 1.2928 0.4445 0.7261 0.026 Uiso 1 1 calc R U . . .
C19 C 1.1983(7) 0.3218(6) 0.7820(2) 0.0234(14) Uani 1 1 d . . . . .
H19 H 1.2642 0.3506 0.8146 0.028 Uiso 1 1 calc R U . . .
C20 C 1.0842(7) 0.2231(5) 0.7862(2) 0.0205(13) Uani 1 1 d . . . . .
H20 H 1.0725 0.1846 0.8217 0.025 Uiso 1 1 calc R U . . .
C21 C 0.9852(7) 0.1797(5) 0.7374(2) 0.0189(12) Uani 1 1 d . . . . .
H21 H 0.9099 0.1115 0.7406 0.023 Uiso 1 1 calc R U . . .
N1 N 0.7075(5) 0.2640(4) 0.62327(18) 0.0124(9) Uani 1 1 d . . . . .
I1 I 0.19714(5) 0.14666(4) 0.45549(2) 0.02418(11) Uani 1 1 d . . . . .
Bi1 Bi 0.52581(2) 0.19537(2) 0.53296(2) 0.01338(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 1.392(7) . ?
C1 C6 1.399(7) . ?
C1 Bi1 2.263(5) . ?
C2 C3 1.385(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(6) . ?
C7 N1 1.475(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.478(6) . ?
C8 C9 1.513(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.391(7) . ?
C9 C10 1.392(7) . ?
C10 C11 1.368(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(7) . ?
C13 H13 0.9300 . ?
C14 Bi1 2.245(5) . ?
C15 N1 1.501(6) . ?
C15 C16 1.501(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.389(7) . ?
C16 C17 1.398(7) . ?
C17 C18 1.375(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.396(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 Bi1 2.537(4) . ?
I1 Bi1 2.9875(4) . ?

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 119.6(5) . . ?
C2 C1 Bi1 125.4(4) . . ?
C6 C1 Bi1 115.0(3) . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.2(5) . . ?
C5 C6 C7 120.8(5) . . ?
C1 C6 C7 119.9(5) . . ?
N1 C7 C6 109.8(4) . . ?
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 . . ?
N1 C8 C9 112.7(4) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C10 119.6(4) . . ?
C14 C9 C8 120.1(4) . . ?
C10 C9 C8 120.0(4) . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 119.4(4) . . ?
C13 C14 Bi1 123.7(4) . . ?
C9 C14 Bi1 116.7(3) . . ?
N1 C15 C16 114.1(4) . . ?
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 . . ?
C21 C16 C17 118.0(5) . . ?
C21 C16 C15 121.5(5) . . ?
C17 C16 C15 120.5(5) . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.2(5) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 119.2(5) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.5(5) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.6(5) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C7 N1 C8 111.1(4) . . ?
C7 N1 C15 112.8(4) . . ?
C8 N1 C15 112.1(4) . . ?
C7 N1 Bi1 102.3(3) . . ?
C8 N1 Bi1 105.2(3) . . ?
C15 N1 Bi1 112.7(3) . . ?
C14 Bi1 C1 96.75(17) . . ?
C14 Bi1 N1 74.08(15) . . ?
C1 Bi1 N1 71.97(16) . . ?
C14 Bi1 I1 91.77(12) . . ?
C1 Bi1 I1 93.27(13) . . ?
N1 Bi1 I1 157.72(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(7) . . . . ?
Bi1 C1 C2 C3 179.8(4) . . . . ?
C1 C2 C3 C4 -0.4(8) . . . . ?
C2 C3 C4 C5 1.4(8) . . . . ?
C3 C4 C5 C6 -1.6(8) . . . . ?
C4 C5 C6 C1 0.8(8) . . . . ?
C4 C5 C6 C7 179.5(5) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
Bi1 C1 C6 C5 -179.9(4) . . . . ?
C2 C1 C6 C7 -178.6(4) . . . . ?
Bi1 C1 C6 C7 1.3(6) . . . . ?
C5 C6 C7 N1 144.0(5) . . . . ?
C1 C6 C7 N1 -37.3(6) . . . . ?
N1 C8 C9 C14 -35.0(6) . . . . ?
N1 C8 C9 C10 151.1(4) . . . . ?
C14 C9 C10 C11 -1.3(7) . . . . ?
C8 C9 C10 C11 172.7(4) . . . . ?
C9 C10 C11 C12 0.5(7) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C11 C12 C13 C14 0.5(7) . . . . ?
C12 C13 C14 C9 -1.3(7) . . . . ?
C12 C13 C14 Bi1 173.9(3) . . . . ?
C10 C9 C14 C13 1.7(7) . . . . ?
C8 C9 C14 C13 -172.3(4) . . . . ?
C10 C9 C14 Bi1 -173.9(3) . . . . ?
C8 C9 C14 Bi1 12.2(6) . . . . ?
N1 C15 C16 C21 92.0(6) . . . . ?
N1 C15 C16 C17 -86.3(5) . . . . ?
C21 C16 C17 C18 -1.2(7) . . . . ?
C15 C16 C17 C18 177.1(4) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
C17 C18 C19 C20 0.6(7) . . . . ?
C18 C19 C20 C21 0.0(7) . . . . ?
C17 C16 C21 C20 1.9(7) . . . . ?
C15 C16 C21 C20 -176.5(5) . . . . ?
C19 C20 C21 C16 -1.3(7) . . . . ?
C6 C7 N1 C8 -64.6(5) . . . . ?
C6 C7 N1 C15 168.6(4) . . . . ?
C6 C7 N1 Bi1 47.2(4) . . . . ?
C9 C8 N1 C7 145.0(4) . . . . ?
C9 C8 N1 C15 -87.7(5) . . . . ?
C9 C8 N1 Bi1 35.1(4) . . . . ?
C16 C15 N1 C7 63.3(6) . . . . ?
C16 C15 N1 C8 -63.0(6) . . . . ?
C16 C15 N1 Bi1 178.6(3) . . . . ?

_refine_diff_density_max         1.236
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.155

_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 1520820'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013/4
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 Bi Cl N'
_chemical_formula_sum            'C21 H19 Bi Cl N'
_chemical_formula_weight         529.80

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.0394(4)
_cell_length_b                   11.5616(4)
_cell_length_c                   15.0742(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.277(4)
_cell_angle_gamma                90
_cell_volume                     1749.66(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    3288
_cell_measurement_theta_min      4.3400
_cell_measurement_theta_max      28.9540

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    10.231
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.35615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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            8593
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.003
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3439
_reflns_number_gt                2973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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)+(0.0237P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3439
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0615
_refine_ls_wR_factor_gt          0.0592
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C14 C 0.1185(5) 0.6421(4) 0.0527(3) 0.0102(10) Uani 1 1 d . . . . .
C13 C 0.0605(5) 0.5541(4) 0.1012(3) 0.0167(12) Uani 1 1 d . . . . .
H13 H -0.0197 0.5667 0.1303 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1222(6) 0.4469(4) 0.1062(3) 0.0178(12) Uani 1 1 d . . . . .
H12 H 0.0853 0.3885 0.1406 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2377(5) 0.4272(4) 0.0602(4) 0.0191(12) Uani 1 1 d . . . . .
H11 H 0.2774 0.3545 0.0619 0.023 Uiso 1 1 calc R U . . .
C10 C 0.2955(6) 0.5152(4) 0.0114(4) 0.0172(12) Uani 1 1 d . . . . .
H10 H 0.3732 0.5014 -0.0202 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2370(5) 0.6246(4) 0.0096(3) 0.0113(11) Uani 1 1 d . . . . .
C8 C 0.3100(5) 0.7268(4) -0.0306(3) 0.0109(11) Uani 1 1 d . . . . .
H8A H 0.3539 0.7703 0.0161 0.013 Uiso 1 1 calc R U . . .
H8B H 0.3777 0.6989 -0.0710 0.013 Uiso 1 1 calc R U . . .
C1 C 0.1531(5) 0.9402(4) 0.0708(3) 0.0122(11) Uani 1 1 d . . . . .
C2 C 0.1385(5) 0.9959(4) 0.1521(4) 0.0157(12) Uani 1 1 d . . . . .
H2 H 0.0699 0.9740 0.1898 0.019 Uiso 1 1 calc R U . . .
C3 C 0.2248(5) 1.0836(4) 0.1777(4) 0.0180(12) Uani 1 1 d . . . . .
H3 H 0.2148 1.1196 0.2324 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3253(5) 1.1168(4) 0.1214(3) 0.0159(12) Uani 1 1 d . . . . .
H4 H 0.3842 1.1750 0.1382 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3387(5) 1.0633(4) 0.0393(3) 0.0140(11) Uani 1 1 d . . . . .
H5 H 0.4061 1.0868 0.0012 0.017 Uiso 1 1 calc R U . . .
C6 C 0.2529(5) 0.9755(4) 0.0138(3) 0.0131(11) Uani 1 1 d . . . . .
C7 C 0.2625(5) 0.9249(4) -0.0783(3) 0.0121(11) Uani 1 1 d . . . . .
H7A H 0.2084 0.9701 -0.1189 0.015 Uiso 1 1 calc R U . . .
H7B H 0.3541 0.9284 -0.0982 0.015 Uiso 1 1 calc R U . . .
C15 C 0.1910(5) 0.7592(4) -0.1710(3) 0.0138(11) Uani 1 1 d . . . . .
H15A H 0.1597 0.6801 -0.1671 0.017 Uiso 1 1 calc R U . . .
H15B H 0.1203 0.8049 -0.1977 0.017 Uiso 1 1 calc R U . . .
C16 C 0.3087(5) 0.7625(4) -0.2301(3) 0.0128(11) Uani 1 1 d . . . . .
C21 C 0.3874(6) 0.6623(4) -0.2405(4) 0.0213(13) Uani 1 1 d . . . . .
H21 H 0.3621 0.5939 -0.2128 0.026 Uiso 1 1 calc R U . . .
C20 C 0.5012(6) 0.6643(5) -0.2913(4) 0.0260(14) Uani 1 1 d . . . . .
H20 H 0.5519 0.5976 -0.2977 0.031 Uiso 1 1 calc R U . . .
C19 C 0.5402(5) 0.7658(5) -0.3327(4) 0.0241(13) Uani 1 1 d . . . . .
H19 H 0.6175 0.7678 -0.3664 0.029 Uiso 1 1 calc R U . . .
C18 C 0.4628(5) 0.8642(5) -0.3235(3) 0.0216(13) Uani 1 1 d . . . . .
H18 H 0.4885 0.9327 -0.3508 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3486(5) 0.8611(5) -0.2743(3) 0.0172(12) Uani 1 1 d . . . . .
H17 H 0.2964 0.9273 -0.2706 0.021 Uiso 1 1 calc R U . . .
N1 N 0.2166(4) 0.8035(3) -0.0791(3) 0.0112(9) Uani 1 1 d . . . . .
Cl1 Cl -0.11561(12) 0.80467(10) 0.16962(9) 0.0155(3) Uani 1 1 d . . . . .
Bi1 Bi 0.00949(2) 0.80648(2) 0.01793(2) 0.01054(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
C14 C9 1.374(7) . ?
C14 C13 1.382(6) . ?
C14 Bi1 2.254(5) . ?
C13 C12 1.387(7) . ?
C13 H13 0.9300 . ?
C12 C11 1.373(7) . ?
C12 H12 0.9300 . ?
C11 C10 1.385(7) . ?
C11 H11 0.9300 . ?
C10 C9 1.395(6) . ?
C10 H10 0.9300 . ?
C9 C8 1.518(6) . ?
C8 N1 1.481(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C6 1.384(7) . ?
C1 C2 1.394(7) . ?
C1 Bi1 2.257(5) . ?
C2 C3 1.387(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(7) . ?
C7 N1 1.477(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C15 C16 1.483(7) . ?
C15 N1 1.498(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.381(7) . ?
C16 C21 1.412(7) . ?
C21 C20 1.378(8) . ?
C21 H21 0.9300 . ?
C20 C19 1.387(8) . ?
C20 H20 0.9300 . ?
C19 C18 1.385(8) . ?
C19 H19 0.9300 . ?
C18 C17 1.368(7) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
N1 Bi1 2.548(4) . ?
Cl1 Bi1 2.6142(12) . ?

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
C9 C14 C13 120.7(4) . . ?
C9 C14 Bi1 115.7(3) . . ?
C13 C14 Bi1 122.6(4) . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C11 C12 C13 119.9(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C11 C10 120.2(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C14 C9 C10 119.3(4) . . ?
C14 C9 C8 119.7(4) . . ?
C10 C9 C8 120.6(4) . . ?
N1 C8 C9 110.9(4) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C6 C1 C2 119.3(5) . . ?
C6 C1 Bi1 116.5(4) . . ?
C2 C1 Bi1 123.9(4) . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 119.6(5) . . ?
C1 C6 C7 120.4(4) . . ?
C5 C6 C7 119.8(4) . . ?
N1 C7 C6 110.8(4) . . ?
N1 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C16 C15 N1 114.4(4) . . ?
C16 C15 H15A 108.7 . . ?
N1 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
N1 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C21 117.3(5) . . ?
C17 C16 C15 123.0(5) . . ?
C21 C16 C15 119.6(5) . . ?
C20 C21 C16 120.9(5) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C21 C20 C19 120.1(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C18 C19 C20 119.3(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C17 C18 C19 120.3(5) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C17 C16 122.0(5) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C7 N1 C8 111.6(4) . . ?
C7 N1 C15 112.6(4) . . ?
C8 N1 C15 111.0(4) . . ?
C7 N1 Bi1 103.7(3) . . ?
C8 N1 Bi1 103.9(3) . . ?
C15 N1 Bi1 113.5(3) . . ?
C14 Bi1 C1 100.77(17) . . ?
C14 Bi1 N1 74.07(15) . . ?
C1 Bi1 N1 71.96(15) . . ?
C14 Bi1 Cl1 91.40(13) . . ?
C1 Bi1 Cl1 90.32(13) . . ?
N1 Bi1 Cl1 153.99(10) . . ?

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 -0.2(8) . . . . ?
Bi1 C14 C13 C12 167.7(4) . . . . ?
C14 C13 C12 C11 -2.6(8) . . . . ?
C13 C12 C11 C10 2.3(8) . . . . ?
C12 C11 C10 C9 0.7(8) . . . . ?
C13 C14 C9 C10 3.1(8) . . . . ?
Bi1 C14 C9 C10 -165.6(4) . . . . ?
C13 C14 C9 C8 -170.2(5) . . . . ?
Bi1 C14 C9 C8 21.2(6) . . . . ?
C11 C10 C9 C14 -3.4(8) . . . . ?
C11 C10 C9 C8 169.8(5) . . . . ?
C14 C9 C8 N1 -44.5(6) . . . . ?
C10 C9 C8 N1 142.3(5) . . . . ?
C6 C1 C2 C3 -1.9(7) . . . . ?
Bi1 C1 C2 C3 -175.0(4) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C4 C5 C6 -0.9(7) . . . . ?
C2 C1 C6 C5 1.7(7) . . . . ?
Bi1 C1 C6 C5 175.3(4) . . . . ?
C2 C1 C6 C7 -173.9(4) . . . . ?
Bi1 C1 C6 C7 -0.3(6) . . . . ?
C4 C5 C6 C1 -0.3(7) . . . . ?
C4 C5 C6 C7 175.3(4) . . . . ?
C1 C6 C7 N1 -32.4(6) . . . . ?
C5 C6 C7 N1 152.0(4) . . . . ?
N1 C15 C16 C17 -81.8(6) . . . . ?
N1 C15 C16 C21 96.2(5) . . . . ?
C17 C16 C21 C20 1.5(8) . . . . ?
C15 C16 C21 C20 -176.6(5) . . . . ?
C16 C21 C20 C19 0.2(9) . . . . ?
C21 C20 C19 C18 -0.8(9) . . . . ?
C20 C19 C18 C17 -0.4(8) . . . . ?
C19 C18 C17 C16 2.2(8) . . . . ?
C21 C16 C17 C18 -2.7(8) . . . . ?
C15 C16 C17 C18 175.3(5) . . . . ?
C6 C7 N1 C8 -69.1(5) . . . . ?
C6 C7 N1 C15 165.3(4) . . . . ?
C6 C7 N1 Bi1 42.2(4) . . . . ?
C9 C8 N1 C7 150.5(4) . . . . ?
C9 C8 N1 C15 -83.0(5) . . . . ?
C9 C8 N1 Bi1 39.3(4) . . . . ?
C16 C15 N1 C7 59.5(5) . . . . ?
C16 C15 N1 C8 -66.4(5) . . . . ?
C16 C15 N1 Bi1 177.0(3) . . . . ?

_refine_diff_density_max         0.920
_refine_diff_density_min         -1.935
_refine_diff_density_rms         0.165

####################################################################### 
# 
# 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_AT-162
_database_code_depnum_ccdc_archive 'CCDC 1520821'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Bi Cl N O'
_chemical_formula_sum            'C17 H19 Bi Cl N O'
_chemical_formula_weight         497.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.0546(3)
_cell_length_b                   18.9853(6)
_cell_length_c                   19.0771(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.059(3)
_cell_angle_gamma                90
_cell_volume                     3279.43(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    110
_cell_measurement_reflns_used    8593
_cell_measurement_theta_min      3.3010
_cell_measurement_theta_max      28.5700

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_F_000             1888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    10.913
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.16047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            33575
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.109
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6413
_reflns_number_gt                5553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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)+(0.0324P)²+1.9371P] 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         6413
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_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 0.2735(6) 0.7781(3) 0.2707(3) 0.0178(13) Uani 1 1 d . . . . .
C13 C 0.1232(6) 0.7902(3) 0.2812(3) 0.0179(13) Uani 1 1 d . . . . .
H13 H 0.0642 0.7554 0.3010 0.021 Uiso 1 1 calc R U . . .
C12 C 0.0615(7) 0.8549(3) 0.2620(3) 0.0236(14) Uani 1 1 d . . . . .
H12 H -0.0380 0.8635 0.2704 0.028 Uiso 1 1 calc R U . . .
C11 C 0.1467(7) 0.9059(3) 0.2306(3) 0.0275(15) Uani 1 1 d . . . . .
H11 H 0.1049 0.9488 0.2179 0.033 Uiso 1 1 calc R U . . .
C10 C 0.2946(7) 0.8931(3) 0.2181(3) 0.0243(14) Uani 1 1 d . . . . .
H10 H 0.3516 0.9266 0.1950 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3582(7) 0.8301(3) 0.2401(3) 0.0208(13) Uani 1 1 d . . . . .
C8 C 0.5247(7) 0.8202(3) 0.2333(3) 0.0240(14) Uani 1 1 d . . . . .
H8A H 0.5586 0.8434 0.1910 0.029 Uiso 1 1 calc R U . . .
H8B H 0.5734 0.8423 0.2729 0.029 Uiso 1 1 calc R U . . .
C1 C 0.4078(6) 0.6133(3) 0.2238(3) 0.0178(12) Uani 1 1 d . . . . .
C2 C 0.3596(7) 0.5448(3) 0.2262(3) 0.0249(14) Uani 1 1 d . . . . .
H2 H 0.3110 0.5279 0.2657 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3841(8) 0.5005(4) 0.1687(3) 0.0350(17) Uani 1 1 d . . . . .
H3 H 0.3528 0.4539 0.1700 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4552(7) 0.5263(4) 0.1096(3) 0.0305(16) Uani 1 1 d . . . . .
H4 H 0.4703 0.4971 0.0711 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5030(7) 0.5946(4) 0.1078(3) 0.0274(15) Uani 1 1 d . . . . .
H5 H 0.5507 0.6115 0.0681 0.033 Uiso 1 1 calc R U . . .
C6 C 0.4810(6) 0.6393(3) 0.1649(3) 0.0214(13) Uani 1 1 d . . . . .
C7 C 0.5256(7) 0.7149(3) 0.1613(3) 0.0243(14) Uani 1 1 d . . . . .
H7A H 0.6093 0.7193 0.1299 0.029 Uiso 1 1 calc R U . . .
H7B H 0.4448 0.7420 0.1415 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7241(7) 0.7376(3) 0.2455(3) 0.0268(15) Uani 1 1 d . . . . .
H15A H 0.7490 0.7668 0.2855 0.032 Uiso 1 1 calc R U . . .
H15B H 0.7795 0.7550 0.2057 0.032 Uiso 1 1 calc R U . . .
C16 C 0.7727(7) 0.6635(3) 0.2605(3) 0.0259(14) Uani 1 1 d . . . . .
H16A H 0.7426 0.6323 0.2229 0.031 Uiso 1 1 calc R U . . .
H16B H 0.8792 0.6613 0.2652 0.031 Uiso 1 1 calc R U . . .
C17 C 0.7272(8) 0.5721(4) 0.3414(4) 0.0406(18) Uani 1 1 d . . . . .
H17A H 0.6787 0.5611 0.3848 0.061 Uiso 1 1 calc R U . . .
H17B H 0.6881 0.5429 0.3048 0.061 Uiso 1 1 calc R U . . .
H17C H 0.8313 0.5636 0.3462 0.061 Uiso 1 1 calc R U . . .
C31 C -0.2160(6) 0.6592(3) 0.5085(3) 0.0169(12) Uani 1 1 d . . . . .
C30 C -0.3684(7) 0.6473(3) 0.5083(3) 0.0220(13) Uani 1 1 d . . . . .
H30 H -0.4309 0.6800 0.4874 0.026 Uiso 1 1 calc R U . . .
C29 C -0.4268(7) 0.5880(3) 0.5384(3) 0.0243(14) Uani 1 1 d . . . . .
H29 H -0.5282 0.5803 0.5368 0.029 Uiso 1 1 calc R U . . .
C28 C -0.3361(7) 0.5395(3) 0.5712(3) 0.0262(15) Uani 1 1 d . . . . .
H28 H -0.3763 0.4997 0.5922 0.031 Uiso 1 1 calc R U . . .
C27 C -0.1850(7) 0.5507(3) 0.5725(3) 0.0237(14) Uani 1 1 d . . . . .
H27 H -0.1239 0.5185 0.5951 0.028 Uiso 1 1 calc R U . . .
C26 C -0.1237(6) 0.6095(3) 0.5404(3) 0.0191(13) Uani 1 1 d . . . . .
C25 C 0.0403(6) 0.6183(3) 0.5375(3) 0.0190(13) Uani 1 1 d . . . . .
H25A H 0.0845 0.5965 0.5784 0.023 Uiso 1 1 calc R U . . .
H25B H 0.0783 0.5947 0.4962 0.023 Uiso 1 1 calc R U . . .
C18 C -0.0761(6) 0.8254(3) 0.5364(3) 0.0155(12) Uani 1 1 d . . . . .
C19 C -0.1191(6) 0.8951(3) 0.5293(3) 0.0205(13) Uani 1 1 d . . . . .
H19 H -0.1763 0.9089 0.4912 0.025 Uiso 1 1 calc R U . . .
C20 C -0.0767(7) 0.9445(3) 0.5794(3) 0.0291(15) Uani 1 1 d . . . . .
H20 H -0.1047 0.9914 0.5743 0.035 Uiso 1 1 calc R U . . .
C21 C 0.0062(7) 0.9242(3) 0.6362(3) 0.0277(15) Uani 1 1 d . . . . .
H21 H 0.0338 0.9574 0.6695 0.033 Uiso 1 1 calc R U . . .
C22 C 0.0489(7) 0.8551(3) 0.6441(3) 0.0227(14) Uani 1 1 d . . . . .
H22 H 0.1053 0.8417 0.6826 0.027 Uiso 1 1 calc R U . . .
C23 C 0.0072(6) 0.8053(3) 0.5941(3) 0.0162(12) Uani 1 1 d . . . . .
C24 C 0.0474(7) 0.7290(3) 0.6025(3) 0.0176(12) Uani 1 1 d . . . . .
H24A H 0.1324 0.7255 0.6333 0.021 Uiso 1 1 calc R U . . .
H24B H -0.0341 0.7046 0.6248 0.021 Uiso 1 1 calc R U . . .
C32 C 0.2420(6) 0.7000(3) 0.5174(3) 0.0181(13) Uani 1 1 d . . . . .
H32A H 0.2999 0.6795 0.5551 0.022 Uiso 1 1 calc R U . . .
H32B H 0.2615 0.6730 0.4753 0.022 Uiso 1 1 calc R U . . .
C33 C 0.2920(6) 0.7739(3) 0.5060(3) 0.0190(13) Uani 1 1 d . . . . .
H33A H 0.2682 0.8024 0.5466 0.023 Uiso 1 1 calc R U . . .
H33B H 0.3981 0.7750 0.4991 0.023 Uiso 1 1 calc R U . . .
C34 C 0.2509(7) 0.8731(3) 0.4352(3) 0.0255(14) Uani 1 1 d . . . . .
H34A H 0.2001 0.8896 0.3942 0.038 Uiso 1 1 calc R U . . .
H34B H 0.2191 0.8996 0.4753 0.038 Uiso 1 1 calc R U . . .
H34C H 0.3554 0.8790 0.4290 0.038 Uiso 1 1 calc R U . . .
O1 O 0.7031(5) 0.6437(2) 0.3247(2) 0.0250(10) Uani 1 1 d . . . . .
O2 O 0.2188(4) 0.8006(2) 0.44569(19) 0.0199(9) Uani 1 1 d . . . . .
Cl1 Cl 0.13540(15) 0.62248(7) 0.34850(7) 0.0164(3) Uani 1 1 d . . . . .
Cl2 Cl -0.35829(15) 0.81010(7) 0.41663(7) 0.0180(3) Uani 1 1 d . . . . .
N1 N 0.5661(5) 0.7457(2) 0.2307(2) 0.0191(11) Uani 1 1 d . . . . .
N2 N 0.0823(5) 0.6933(2) 0.5352(2) 0.0148(10) Uani 1 1 d . . . . .
Bi1 Bi 0.39403(2) 0.68569(2) 0.31755(2) 0.01593(7) Uani 1 1 d . . . . .
Bi2 Bi -0.10130(2) 0.74685(2) 0.44963(2) 0.01511(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
C14 C9 1.379(8) . ?
C14 C13 1.395(8) . ?
C14 Bi1 2.251(6) . ?
C13 C12 1.398(8) . ?
C13 H13 0.9300 . ?
C12 C11 1.375(8) . ?
C12 H12 0.9300 . ?
C11 C10 1.382(9) . ?
C11 H11 0.9300 . ?
C10 C9 1.393(8) . ?
C10 H10 0.9300 . ?
C9 C8 1.525(9) . ?
C8 N1 1.463(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.372(8) . ?
C1 C6 1.396(8) . ?
C1 Bi1 2.260(5) . ?
C2 C3 1.400(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.494(8) . ?
C7 N1 1.492(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C15 N1 1.466(8) . ?
C15 C16 1.501(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.427(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O1 1.414(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C31 C26 1.398(8) . ?
C31 C30 1.398(8) . ?
C31 Bi2 2.261(5) . ?
C30 C29 1.370(8) . ?
C30 H30 0.9300 . ?
C29 C28 1.382(9) . ?
C29 H29 0.9300 . ?
C28 C27 1.385(9) . ?
C28 H28 0.9300 . ?
C27 C26 1.390(8) . ?
C27 H27 0.9300 . ?
C26 C25 1.496(8) . ?
C25 N2 1.474(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C18 C19 1.387(8) . ?
C18 C23 1.388(8) . ?
C18 Bi2 2.239(5) . ?
C19 C20 1.392(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.394(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.502(8) . ?
C24 N2 1.487(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C32 C33 1.490(8) . ?
C32 N2 1.491(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 O2 1.422(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 O2 1.420(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
Cl1 Bi1 2.6973(13) . ?
Cl2 Bi2 2.6926(14) . ?
N1 Bi1 2.545(5) . ?
N2 Bi2 2.540(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
C9 C14 C13 119.1(5) . . ?
C9 C14 Bi1 117.1(4) . . ?
C13 C14 Bi1 123.0(4) . . ?
C14 C13 C12 119.8(6) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C11 C12 C13 120.6(6) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C11 C10 119.7(6) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C10 C9 120.0(6) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C14 C9 C10 120.8(6) . . ?
C14 C9 C8 119.9(5) . . ?
C10 C9 C8 119.3(5) . . ?
N1 C8 C9 112.0(5) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C2 C1 C6 120.8(5) . . ?
C2 C1 Bi1 122.2(4) . . ?
C6 C1 Bi1 116.7(4) . . ?
C1 C2 C3 119.5(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.8(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.8(6) . . ?
C5 C6 C7 120.7(5) . . ?
C1 C6 C7 120.4(5) . . ?
N1 C7 C6 113.7(5) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N1 C15 C16 114.9(5) . . ?
N1 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
N1 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
O1 C16 C15 106.3(5) . . ?
O1 C16 H16A 110.5 . . ?
C15 C16 H16A 110.5 . . ?
O1 C16 H16B 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C31 C30 118.8(5) . . ?
C26 C31 Bi2 116.0(4) . . ?
C30 C31 Bi2 124.8(4) . . ?
C29 C30 C31 120.8(6) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C30 C29 C28 120.5(6) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C28 C27 119.6(6) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C27 C26 120.6(6) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C26 C31 119.7(6) . . ?
C27 C26 C25 120.2(5) . . ?
C31 C26 C25 120.1(5) . . ?
N2 C25 C26 111.4(5) . . ?
N2 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
N2 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C19 C18 C23 119.4(5) . . ?
C19 C18 Bi2 122.4(4) . . ?
C23 C18 Bi2 117.3(4) . . ?
C18 C19 C20 120.0(6) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.2(6) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.5(6) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 119.7(6) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 120.3(5) . . ?
C18 C23 C24 118.7(5) . . ?
C22 C23 C24 121.0(5) . . ?
N2 C24 C23 113.6(4) . . ?
N2 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
N2 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C33 C32 N2 114.1(5) . . ?
C33 C32 H32A 108.7 . . ?
N2 C32 H32A 108.7 . . ?
C33 C32 H32B 108.7 . . ?
N2 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
O2 C33 C32 108.2(5) . . ?
O2 C33 H33A 110.0 . . ?
C32 C33 H33A 110.0 . . ?
O2 C33 H33B 110.0 . . ?
C32 C33 H33B 110.0 . . ?
H33A C33 H33B 108.4 . . ?
O2 C34 H34A 109.5 . . ?
O2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C17 O1 C16 112.3(5) . . ?
C34 O2 C33 111.4(4) . . ?
C8 N1 C15 110.2(5) . . ?
C8 N1 C7 110.3(5) . . ?
C15 N1 C7 111.6(5) . . ?
C8 N1 Bi1 104.7(3) . . ?
C15 N1 Bi1 115.1(3) . . ?
C7 N1 Bi1 104.6(3) . . ?
C25 N2 C24 111.1(4) . . ?
C25 N2 C32 109.8(4) . . ?
C24 N2 C32 111.4(4) . . ?
C25 N2 Bi2 103.7(3) . . ?
C24 N2 Bi2 103.5(3) . . ?
C32 N2 Bi2 117.0(3) . . ?
C14 Bi1 C1 100.8(2) . . ?
C14 Bi1 N1 71.89(18) . . ?
C1 Bi1 N1 73.89(18) . . ?
C14 Bi1 Cl1 90.76(15) . . ?
C1 Bi1 Cl1 87.20(15) . . ?
N1 Bi1 Cl1 150.90(11) . . ?
C18 Bi2 C31 99.77(19) . . ?
C18 Bi2 N2 74.07(17) . . ?
C31 Bi2 N2 71.76(18) . . ?
C18 Bi2 Cl2 87.90(15) . . ?
C31 Bi2 Cl2 92.71(15) . . ?
N2 Bi2 Cl2 153.30(10) . . ?

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(8) . . . . ?
Bi1 C14 C13 C12 168.0(4) . . . . ?
C14 C13 C12 C11 2.1(9) . . . . ?
C13 C12 C11 C10 -0.1(9) . . . . ?
C12 C11 C10 C9 -2.9(9) . . . . ?
C13 C14 C9 C10 -1.7(8) . . . . ?
Bi1 C14 C9 C10 -171.6(4) . . . . ?
C13 C14 C9 C8 175.3(5) . . . . ?
Bi1 C14 C9 C8 5.5(7) . . . . ?
C11 C10 C9 C14 3.8(9) . . . . ?
C11 C10 C9 C8 -173.2(5) . . . . ?
C14 C9 C8 N1 26.3(7) . . . . ?
C10 C9 C8 N1 -156.6(5) . . . . ?
C6 C1 C2 C3 -0.1(9) . . . . ?
Bi1 C1 C2 C3 -173.8(5) . . . . ?
C1 C2 C3 C4 -0.7(10) . . . . ?
C2 C3 C4 C5 0.9(10) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C4 C5 C6 C1 -0.6(9) . . . . ?
C4 C5 C6 C7 -176.5(6) . . . . ?
C2 C1 C6 C5 0.7(9) . . . . ?
Bi1 C1 C6 C5 174.8(4) . . . . ?
C2 C1 C6 C7 176.6(6) . . . . ?
Bi1 C1 C6 C7 -9.3(7) . . . . ?
C5 C6 C7 N1 -151.3(5) . . . . ?
C1 C6 C7 N1 33.0(8) . . . . ?
N1 C15 C16 O1 -65.8(6) . . . . ?
C26 C31 C30 C29 -0.2(8) . . . . ?
Bi2 C31 C30 C29 172.0(4) . . . . ?
C31 C30 C29 C28 1.5(9) . . . . ?
C30 C29 C28 C27 -0.9(9) . . . . ?
C29 C28 C27 C26 -1.0(9) . . . . ?
C28 C27 C26 C31 2.3(9) . . . . ?
C28 C27 C26 C25 -175.5(5) . . . . ?
C30 C31 C26 C27 -1.7(8) . . . . ?
Bi2 C31 C26 C27 -174.6(4) . . . . ?
C30 C31 C26 C25 176.1(5) . . . . ?
Bi2 C31 C26 C25 3.2(7) . . . . ?
C27 C26 C25 N2 -151.7(5) . . . . ?
C31 C26 C25 N2 30.6(7) . . . . ?
C23 C18 C19 C20 1.0(8) . . . . ?
Bi2 C18 C19 C20 -168.1(4) . . . . ?
C18 C19 C20 C21 -0.7(9) . . . . ?
C19 C20 C21 C22 0.3(10) . . . . ?
C20 C21 C22 C23 -0.2(9) . . . . ?
C19 C18 C23 C22 -0.9(8) . . . . ?
Bi2 C18 C23 C22 168.8(4) . . . . ?
C19 C18 C23 C24 177.5(5) . . . . ?
Bi2 C18 C23 C24 -12.8(7) . . . . ?
C21 C22 C23 C18 0.5(9) . . . . ?
C21 C22 C23 C24 -177.9(5) . . . . ?
C18 C23 C24 N2 37.5(7) . . . . ?
C22 C23 C24 N2 -144.1(5) . . . . ?
N2 C32 C33 O2 -65.1(6) . . . . ?
C15 C16 O1 C17 173.9(5) . . . . ?
C32 C33 O2 C34 174.7(4) . . . . ?
C9 C8 N1 C15 -162.9(5) . . . . ?
C9 C8 N1 C7 73.5(6) . . . . ?
C9 C8 N1 Bi1 -38.6(5) . . . . ?
C16 C15 N1 C8 166.6(5) . . . . ?
C16 C15 N1 C7 -70.5(6) . . . . ?
C16 C15 N1 Bi1 48.6(6) . . . . ?
C6 C7 N1 C8 -146.8(5) . . . . ?
C6 C7 N1 C15 90.3(6) . . . . ?
C6 C7 N1 Bi1 -34.8(5) . . . . ?
C26 C25 N2 C24 68.1(6) . . . . ?
C26 C25 N2 C32 -168.3(4) . . . . ?
C26 C25 N2 Bi2 -42.4(5) . . . . ?
C23 C24 N2 C25 -148.4(5) . . . . ?
C23 C24 N2 C32 88.9(6) . . . . ?
C23 C24 N2 Bi2 -37.7(5) . . . . ?
C33 C32 N2 C25 173.6(4) . . . . ?
C33 C32 N2 C24 -62.9(6) . . . . ?
C33 C32 N2 Bi2 55.8(5) . . . . ?

_refine_diff_density_max         2.407
_refine_diff_density_min         -1.625
_refine_diff_density_rms         0.168

####################################################################### 
# 
# 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 1520822'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 Bi I N'
_chemical_formula_sum            'C22 H21 Bi I N'
_chemical_formula_weight         635.28

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   19.5719(6)
_cell_length_b                   20.7636(6)
_cell_length_c                   19.6683(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.297(3)
_cell_angle_gamma                90
_cell_volume                     7979.6(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    110
_cell_measurement_reflns_used    8732
_cell_measurement_theta_min      3.5960
_cell_measurement_theta_max      27.8100

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_F_000             4736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    10.390
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.23251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_reflns_number            46954
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.856
_diffrn_reflns_theta_max         24.998
_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             14024
_reflns_number_gt                10724
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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)+(0.0294P)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         14024
_refine_ls_number_parameters     889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0792
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.002
_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 -0.2253(3) 0.0999(3) 0.6105(4) 0.0152(17) Uani 1 1 d . . . . .
C2 C -0.2455(4) 0.1403(3) 0.5562(4) 0.0179(18) Uani 1 1 d . . . . .
H2 H -0.2301 0.1826 0.5554 0.021 Uiso 1 1 calc R U . . .
C3 C -0.2884(4) 0.1170(4) 0.5040(4) 0.023(2) Uani 1 1 d . . . . .
H3 H -0.3015 0.1440 0.4678 0.028 Uiso 1 1 calc R U . . .
C4 C -0.3124(4) 0.0540(4) 0.5042(4) 0.0208(19) Uani 1 1 d . . . . .
H4 H -0.3415 0.0387 0.4688 0.025 Uiso 1 1 calc R U . . .
C5 C -0.2918(4) 0.0146(4) 0.5586(4) 0.0209(19) Uani 1 1 d . . . . .
H5 H -0.3077 -0.0276 0.5595 0.025 Uiso 1 1 calc R U . . .
C6 C -0.2486(4) 0.0363(3) 0.6113(4) 0.0146(17) Uani 1 1 d . . . . .
C7 C -0.2253(4) -0.0083(3) 0.6692(4) 0.0204(19) Uani 1 1 d . . . . .
H7A H -0.2552 -0.0036 0.7065 0.024 Uiso 1 1 calc R U . . .
H7B H -0.2275 -0.0526 0.6538 0.024 Uiso 1 1 calc R U . . .
C14 C -0.0570(4) 0.1040(3) 0.6576(4) 0.0154(17) Uani 1 1 d . . . . .
C13 C -0.0049(4) 0.1491(4) 0.6490(4) 0.0198(19) Uani 1 1 d . . . . .
H13 H -0.0108 0.1918 0.6617 0.024 Uiso 1 1 calc R U . . .
C12 C 0.0550(4) 0.1299(4) 0.6219(4) 0.026(2) Uani 1 1 d . . . . .
H12 H 0.0900 0.1596 0.6176 0.031 Uiso 1 1 calc R U . . .
C11 C 0.0640(4) 0.0670(4) 0.6009(4) 0.0224(19) Uani 1 1 d . . . . .
H11 H 0.1043 0.0548 0.5815 0.027 Uiso 1 1 calc R U . . .
C10 C 0.0122(4) 0.0223(4) 0.6089(4) 0.025(2) Uani 1 1 d . . . . .
H10 H 0.0180 -0.0201 0.5950 0.031 Uiso 1 1 calc R U . . .
C9 C -0.0483(4) 0.0403(3) 0.6376(4) 0.0166(18) Uani 1 1 d . . . . .
C8 C -0.1047(4) -0.0085(3) 0.6410(4) 0.0156(17) Uani 1 1 d . . . . .
H8A H -0.1289 -0.0115 0.5966 0.019 Uiso 1 1 calc R U . . .
H8B H -0.0848 -0.0504 0.6516 0.019 Uiso 1 1 calc R U . . .
C15 C -0.1336(4) -0.0168(3) 0.7614(4) 0.0164(18) Uani 1 1 d . . . . .
H15A H -0.1595 0.0062 0.7943 0.020 Uiso 1 1 calc R U . . .
H15B H -0.0857 -0.0065 0.7709 0.020 Uiso 1 1 calc R U . . .
C16 C -0.1433(4) -0.0895(3) 0.7726(4) 0.0221(19) Uani 1 1 d . . . . .
H16A H -0.1914 -0.1004 0.7658 0.027 Uiso 1 1 calc R U . . .
H16B H -0.1183 -0.1134 0.7397 0.027 Uiso 1 1 calc R U . . .
C17 C -0.1179(4) -0.1078(3) 0.8429(4) 0.0214(14) Uani 1 1 d . . . . .
C18 C -0.1512(4) -0.0874(3) 0.8996(4) 0.0190(19) Uani 1 1 d . . . . .
H18 H -0.1911 -0.0632 0.8933 0.023 Uiso 1 1 calc R U . . .
C19 C -0.1267(4) -0.1019(3) 0.9648(4) 0.024(2) Uani 1 1 d . . . . .
H19 H -0.1496 -0.0865 1.0017 0.029 Uiso 1 1 calc R U . . .
C20 C -0.0688(4) -0.1390(4) 0.9763(4) 0.023(2) Uani 1 1 d . . . . .
H20 H -0.0529 -0.1495 1.0204 0.028 Uiso 1 1 calc R U . . .
C21 C -0.0350(4) -0.1603(4) 0.9207(5) 0.026(2) Uani 1 1 d . . . . .
H21 H 0.0043 -0.1851 0.9275 0.031 Uiso 1 1 calc R U . . .
C22 C -0.0587(4) -0.1451(3) 0.8550(4) 0.0215(19) Uani 1 1 d . . . . .
H22 H -0.0351 -0.1599 0.8183 0.026 Uiso 1 1 calc R U . . .
C23 C 0.2278(4) 0.0800(3) 0.8679(4) 0.0178(18) Uani 1 1 d . . . . .
C24 C 0.2568(4) 0.1298(3) 0.9084(4) 0.0134(17) Uani 1 1 d . . . . .
H24 H 0.2450 0.1723 0.8989 0.016 Uiso 1 1 calc R U . . .
C25 C 0.3024(4) 0.1159(4) 0.9619(4) 0.0194(19) Uani 1 1 d . . . . .
H25 H 0.3200 0.1490 0.9895 0.023 Uiso 1 1 calc R U . . .
C26 C 0.3222(4) 0.0542(4) 0.9750(4) 0.0219(19) Uani 1 1 d . . . . .
H26 H 0.3547 0.0457 1.0103 0.026 Uiso 1 1 calc R U . . .
C27 C 0.2944(4) 0.0038(4) 0.9363(4) 0.0185(18) Uani 1 1 d . . . . .
H27 H 0.3075 -0.0384 0.9463 0.022 Uiso 1 1 calc R U . . .
C28 C 0.2468(4) 0.0161(3) 0.8824(4) 0.0137(17) Uani 1 1 d . . . . .
C29 C 0.2161(4) -0.0378(3) 0.8390(4) 0.0146(17) Uani 1 1 d . . . . .
H29A H 0.2421 -0.0438 0.7990 0.018 Uiso 1 1 calc R U . . .
H29B H 0.2174 -0.0777 0.8646 0.018 Uiso 1 1 calc R U . . .
C36 C 0.0569(4) 0.0882(3) 0.8341(4) 0.0151(17) Uani 1 1 d . . . . .
C35 C 0.0068(4) 0.1360(3) 0.8332(4) 0.0197(19) Uani 1 1 d . . . . .
H35 H 0.0135 0.1741 0.8096 0.024 Uiso 1 1 calc R U . . .
C34 C -0.0533(4) 0.1274(4) 0.8672(4) 0.0207(19) Uani 1 1 d . . . . .
H34 H -0.0869 0.1591 0.8657 0.025 Uiso 1 1 calc R U . . .
C33 C -0.0620(4) 0.0713(4) 0.9027(4) 0.0215(19) Uani 1 1 d . . . . .
H33 H -0.1019 0.0655 0.9256 0.026 Uiso 1 1 calc R U . . .
C32 C -0.0129(4) 0.0234(4) 0.9053(4) 0.0174(18) Uani 1 1 d . . . . .
H32 H -0.0196 -0.0142 0.9297 0.021 Uiso 1 1 calc R U . . .
C31 C 0.0468(4) 0.0317(3) 0.8710(4) 0.0154(17) Uani 1 1 d . . . . .
C30 C 0.1022(4) -0.0183(3) 0.8785(4) 0.0142(17) Uani 1 1 d . . . . .
H30A H 0.1315 -0.0087 0.9186 0.017 Uiso 1 1 calc R U . . .
H30B H 0.0815 -0.0601 0.8851 0.017 Uiso 1 1 calc R U . . .
C37 C 0.1103(4) -0.0649(3) 0.7662(4) 0.0173(18) Uani 1 1 d . . . . .
H37B H 0.0666 -0.0462 0.7510 0.021 Uiso 1 1 calc R U . . .
H37A H 0.1010 -0.1057 0.7879 0.021 Uiso 1 1 calc R U . . .
C38 C 0.1515(4) -0.0780(3) 0.7038(4) 0.0214(14) Uani 1 1 d . . . . .
H38A H 0.1678 -0.0374 0.6864 0.026 Uiso 1 1 calc R U . . .
H38B H 0.1910 -0.1041 0.7172 0.026 Uiso 1 1 calc R U . . .
C39 C 0.1097(4) -0.1119(3) 0.6483(4) 0.0182(18) Uani 1 1 d . . . . .
C40 C 0.1240(4) -0.1012(3) 0.5808(4) 0.0195(19) Uani 1 1 d . . . . .
H40 H 0.1597 -0.0737 0.5710 0.023 Uiso 1 1 calc R U . . .
C41 C 0.0862(4) -0.1306(4) 0.5280(4) 0.026(2) Uani 1 1 d . . . . .
H41 H 0.0963 -0.1227 0.4832 0.031 Uiso 1 1 calc R U . . .
C42 C 0.0332(4) -0.1719(4) 0.5420(4) 0.026(2) Uani 1 1 d . . . . .
H42 H 0.0072 -0.1913 0.5066 0.031 Uiso 1 1 calc R U . . .
C43 C 0.0192(4) -0.1841(4) 0.6075(5) 0.028(2) Uani 1 1 d . . . . .
H43 H -0.0159 -0.2124 0.6168 0.033 Uiso 1 1 calc R U . . .
C44 C 0.0569(4) -0.1548(3) 0.6606(4) 0.0199(19) Uani 1 1 d . . . . .
H44 H 0.0469 -0.1638 0.7053 0.024 Uiso 1 1 calc R U . . .
C58 C 0.2708(3) 0.1656(3) 0.6081(4) 0.0148(17) Uani 1 1 d . . . . .
C57 C 0.2436(4) 0.1169(4) 0.5666(4) 0.0186(18) Uani 1 1 d . . . . .
H57 H 0.2537 0.0742 0.5771 0.022 Uiso 1 1 calc R U . . .
C56 C 0.2012(4) 0.1314(4) 0.5092(4) 0.025(2) Uani 1 1 d . . . . .
H56 H 0.1845 0.0985 0.4808 0.030 Uiso 1 1 calc R U . . .
C55 C 0.1839(4) 0.1947(4) 0.4947(4) 0.0225(19) Uani 1 1 d . . . . .
H55 H 0.1547 0.2048 0.4573 0.027 Uiso 1 1 calc R U . . .
C54 C 0.2111(4) 0.2432(4) 0.5373(4) 0.0221(19) Uani 1 1 d . . . . .
H54 H 0.2001 0.2859 0.5276 0.027 Uiso 1 1 calc R U . . .
C53 C 0.2537(4) 0.2291(3) 0.5931(4) 0.0152(17) Uani 1 1 d . . . . .
C52 C 0.2827(4) 0.2823(3) 0.6384(4) 0.0195(18) Uani 1 1 d . . . . .
H52A H 0.2833 0.3224 0.6131 0.023 Uiso 1 1 calc R U . . .
H52B H 0.2543 0.2883 0.6768 0.023 Uiso 1 1 calc R U . . .
C45 C 0.4406(4) 0.1540(3) 0.6495(4) 0.0166(18) Uani 1 1 d . . . . .
C46 C 0.4882(4) 0.1053(3) 0.6527(4) 0.0193(19) Uani 1 1 d . . . . .
H46 H 0.4793 0.0672 0.6754 0.023 Uiso 1 1 calc R U . . .
C47 C 0.5497(4) 0.1131(4) 0.6218(4) 0.026(2) Uani 1 1 d . . . . .
H47 H 0.5824 0.0805 0.6243 0.031 Uiso 1 1 calc R U . . .
C48 C 0.5624(4) 0.1693(4) 0.5874(4) 0.029(2) Uani 1 1 d . . . . .
H48 H 0.6035 0.1743 0.5665 0.035 Uiso 1 1 calc R U . . .
C49 C 0.5147(4) 0.2181(4) 0.5835(4) 0.024(2) Uani 1 1 d . . . . .
H49 H 0.5233 0.2559 0.5601 0.029 Uiso 1 1 calc R U . . .
C50 C 0.4531(4) 0.2100(3) 0.6153(4) 0.0177(18) Uani 1 1 d . . . . .
C51 C 0.3990(4) 0.2619(3) 0.6054(4) 0.0165(18) Uani 1 1 d . . . . .
H51A H 0.4212 0.3033 0.6007 0.020 Uiso 1 1 calc R U . . .
H51B H 0.3716 0.2535 0.5637 0.020 Uiso 1 1 calc R U . . .
C59 C 0.3852(4) 0.3084(3) 0.7165(4) 0.0213(19) Uani 1 1 d . . . . .
H59B H 0.3946 0.3496 0.6957 0.026 Uiso 1 1 calc R U . . .
H59A H 0.4286 0.2901 0.7329 0.026 Uiso 1 1 calc R U . . .
C60 C 0.3417(4) 0.3200(3) 0.7773(4) 0.0205(19) Uani 1 1 d . . . . .
H60A H 0.3030 0.3468 0.7628 0.025 Uiso 1 1 calc R U . . .
H60B H 0.3240 0.2790 0.7921 0.025 Uiso 1 1 calc R U . . .
C61 C 0.3799(4) 0.3519(3) 0.8369(4) 0.0192(19) Uani 1 1 d . . . . .
C66 C 0.3579(4) 0.3403(3) 0.9021(4) 0.024(2) Uani 1 1 d . . . . .
H66 H 0.3198 0.3145 0.9077 0.028 Uiso 1 1 calc R U . . .
C65 C 0.3931(5) 0.3674(4) 0.9587(5) 0.033(2) Uani 1 1 d . . . . .
H65 H 0.3787 0.3596 1.0022 0.039 Uiso 1 1 calc R U . . .
C64 C 0.4491(5) 0.4056(4) 0.9503(5) 0.031(2) Uani 1 1 d . . . . .
H64 H 0.4728 0.4233 0.9881 0.037 Uiso 1 1 calc R U . . .
C63 C 0.4705(4) 0.4178(4) 0.8861(5) 0.027(2) Uani 1 1 d . . . . .
H63 H 0.5087 0.4436 0.8810 0.032 Uiso 1 1 calc R U . . .
C62 C 0.4362(4) 0.3924(3) 0.8298(4) 0.0210(19) Uani 1 1 d . . . . .
H62 H 0.4504 0.4020 0.7866 0.025 Uiso 1 1 calc R U . . .
C67 C 0.2716(4) -0.1520(3) 1.1269(4) 0.0145(17) Uani 1 1 d . . . . .
C68 C 0.2481(4) -0.1118(4) 1.0735(4) 0.0177(18) Uani 1 1 d . . . . .
H68 H 0.2634 -0.0695 1.0717 0.021 Uiso 1 1 calc R U . . .
C69 C 0.2021(4) -0.1352(4) 1.0233(4) 0.0209(19) Uani 1 1 d . . . . .
H69 H 0.1871 -0.1086 0.9874 0.025 Uiso 1 1 calc R U . . .
C70 C 0.1785(4) -0.1971(4) 1.0261(4) 0.024(2) Uani 1 1 d . . . . .
H70 H 0.1463 -0.2120 0.9932 0.029 Uiso 1 1 calc R U . . .
C71 C 0.2028(4) -0.2376(4) 1.0783(4) 0.0197(18) Uani 1 1 d . . . . .
H71 H 0.1883 -0.2803 1.0791 0.024 Uiso 1 1 calc R U . . .
C72 C 0.2481(4) -0.2150(3) 1.1287(4) 0.0155(17) Uani 1 1 d . . . . .
C73 C 0.2748(4) -0.2594(3) 1.1854(4) 0.0171(18) Uani 1 1 d . . . . .
H73A H 0.2463 -0.2556 1.2239 0.021 Uiso 1 1 calc R U . . .
H73B H 0.2727 -0.3037 1.1697 0.021 Uiso 1 1 calc R U . . .
C80 C 0.4420(3) -0.1454(3) 1.1729(4) 0.0128(17) Uani 1 1 d . . . . .
C79 C 0.4945(4) -0.1012(4) 1.1675(4) 0.0178(18) Uani 1 1 d . . . . .
H79 H 0.4879 -0.0586 1.1806 0.021 Uiso 1 1 calc R U . . .
C78 C 0.5569(4) -0.1196(4) 1.1429(4) 0.0203(19) Uani 1 1 d . . . . .
H78 H 0.5923 -0.0900 1.1405 0.024 Uiso 1 1 calc R U . . .
C77 C 0.5653(4) -0.1829(4) 1.1219(4) 0.0219(19) Uani 1 1 d . . . . .
H77 H 0.6066 -0.1956 1.1050 0.026 Uiso 1 1 calc R U . . .
C76 C 0.5131(4) -0.2267(4) 1.1259(4) 0.0229(19) Uani 1 1 d . . . . .
H76 H 0.5193 -0.2688 1.1113 0.027 Uiso 1 1 calc R U . . .
C75 C 0.4512(4) -0.2091(3) 1.1516(4) 0.0162(18) Uani 1 1 d . . . . .
C74 C 0.3940(4) -0.2574(3) 1.1533(4) 0.0153(17) Uani 1 1 d . . . . .
H74A H 0.3691 -0.2581 1.1093 0.018 Uiso 1 1 calc R U . . .
H74B H 0.4133 -0.2999 1.1617 0.018 Uiso 1 1 calc R U . . .
C81 C 0.3697(4) -0.2680(3) 1.2741(4) 0.0200(19) Uani 1 1 d . . . . .
H81A H 0.3465 -0.2446 1.3086 0.024 Uiso 1 1 calc R U . . .
H81B H 0.4182 -0.2591 1.2811 0.024 Uiso 1 1 calc R U . . .
C82 C 0.3584(4) -0.3404(3) 1.2853(4) 0.023(2) Uani 1 1 d . . . . .
H82A H 0.3098 -0.3496 1.2821 0.028 Uiso 1 1 calc R U . . .
H82B H 0.3796 -0.3646 1.2499 0.028 Uiso 1 1 calc R U . . .
C83 C 0.3886(4) -0.3612(3) 1.3541(4) 0.0188(19) Uani 1 1 d . . . . .
C88 C 0.4443(4) -0.4015(4) 1.3599(4) 0.026(2) Uani 1 1 d . . . . .
H88 H 0.4633 -0.4173 1.3210 0.031 Uiso 1 1 calc R U . . .
C87 C 0.4720(4) -0.4183(4) 1.4235(5) 0.031(2) Uani 1 1 d . . . . .
H87 H 0.5098 -0.4455 1.4270 0.037 Uiso 1 1 calc R U . . .
C86 C 0.4452(5) -0.3960(4) 1.4815(5) 0.034(2) Uani 1 1 d . . . . .
H86 H 0.4646 -0.4073 1.5241 0.040 Uiso 1 1 calc R U . . .
C85 C 0.3884(5) -0.3561(4) 1.4756(5) 0.031(2) Uani 1 1 d . . . . .
H85 H 0.3690 -0.3407 1.5145 0.037 Uiso 1 1 calc R U . . .
C84 C 0.3606(4) -0.3392(3) 1.4123(4) 0.023(2) Uani 1 1 d . . . . .
H84 H 0.3223 -0.3125 1.4088 0.027 Uiso 1 1 calc R U . . .
I1 I -0.14993(3) 0.26610(2) 0.66315(3) 0.02293(13) Uani 1 1 d . . . . .
I2 I 0.15536(3) 0.23688(2) 0.78615(3) 0.02568(14) Uani 1 1 d . . . . .
I3 I 0.33786(3) 0.00646(2) 0.69326(3) 0.02619(14) Uani 1 1 d . . . . .
I4 I 0.34765(3) 0.01431(2) 1.17209(3) 0.02300(13) Uani 1 1 d . . . . .
Bi1 Bi -0.15675(2) 0.12730(2) 0.70246(2) 0.01412(8) Uani 1 1 d . . . . .
Bi2 Bi 0.15317(2) 0.09310(2) 0.77717(2) 0.01367(8) Uani 1 1 d . . . . .
Bi3 Bi 0.34064(2) 0.15088(2) 0.70234(2) 0.01488(8) Uani 1 1 d . . . . .
Bi4 Bi 0.34226(2) -0.12272(2) 1.21632(2) 0.01421(8) Uani 1 1 d . . . . .
N1 N -0.1543(3) 0.0077(3) 0.6928(3) 0.0152(15) Uani 1 1 d . . . . .
N2 N 0.1444(3) -0.0211(3) 0.8182(3) 0.0136(10) Uani 1 1 d . . . . .
N3 N 0.3533(3) 0.2651(3) 0.6633(3) 0.0130(14) Uani 1 1 d . . . . .
N4 N 0.3460(3) -0.2425(3) 1.2065(3) 0.0136(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
C1 C2 1.396(10) . ?
C1 C6 1.398(9) . ?
C1 Bi1 2.262(7) . ?
C2 C3 1.376(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.517(10) . ?
C7 N1 1.476(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C9 1.392(10) . ?
C14 C13 1.401(10) . ?
C14 Bi1 2.242(7) . ?
C13 C12 1.374(11) . ?
C13 H13 0.9300 . ?
C12 C11 1.384(10) . ?
C12 H12 0.9300 . ?
C11 C10 1.391(10) . ?
C11 H11 0.9300 . ?
C10 C9 1.392(11) . ?
C10 H10 0.9300 . ?
C9 C8 1.503(10) . ?
C8 N1 1.487(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 N1 1.476(9) . ?
C15 C16 1.539(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.492(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.389(11) . ?
C17 C22 1.403(10) . ?
C18 C19 1.377(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(11) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.402(9) . ?
C23 C24 1.406(10) . ?
C23 Bi2 2.256(7) . ?
C24 C25 1.371(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.359(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.387(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.395(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.512(9) . ?
C29 N2 1.480(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C36 C35 1.393(10) . ?
C36 C31 1.398(10) . ?
C36 Bi2 2.250(8) . ?
C35 C34 1.398(11) . ?
C35 H35 0.9300 . ?
C34 C33 1.373(10) . ?
C34 H34 0.9300 . ?
C33 C32 1.384(10) . ?
C33 H33 0.9300 . ?
C32 C31 1.391(10) . ?
C32 H32 0.9300 . ?
C31 C30 1.503(9) . ?
C30 N2 1.484(9) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C37 N2 1.497(9) . ?
C37 C38 1.532(11) . ?
C37 H37B 0.9700 . ?
C37 H37A 0.9700 . ?
C38 C39 1.501(10) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.391(11) . ?
C39 C44 1.394(10) . ?
C40 C41 1.382(11) . ?
C40 H40 0.9300 . ?
C41 C42 1.387(11) . ?
C41 H41 0.9300 . ?
C42 C43 1.355(11) . ?
C42 H42 0.9300 . ?
C43 C44 1.386(10) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C58 C57 1.385(10) . ?
C58 C53 1.389(10) . ?
C58 Bi3 2.260(7) . ?
C57 C56 1.395(11) . ?
C57 H57 0.9300 . ?
C56 C55 1.383(10) . ?
C56 H56 0.9300 . ?
C55 C54 1.395(10) . ?
C55 H55 0.9300 . ?
C54 C53 1.371(10) . ?
C54 H54 0.9300 . ?
C53 C52 1.510(10) . ?
C52 N3 1.483(9) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C45 C50 1.373(10) . ?
C45 C46 1.374(10) . ?
C45 Bi3 2.268(8) . ?
C46 C47 1.389(11) . ?
C46 H46 0.9300 . ?
C47 C48 1.378(12) . ?
C47 H47 0.9300 . ?
C48 C49 1.376(11) . ?
C48 H48 0.9300 . ?
C49 C50 1.399(10) . ?
C49 H49 0.9300 . ?
C50 C51 1.517(10) . ?
C51 N3 1.488(9) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C59 N3 1.490(9) . ?
C59 C60 1.526(11) . ?
C59 H59B 0.9700 . ?
C59 H59A 0.9700 . ?
C60 C61 1.507(10) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C61 C66 1.397(11) . ?
C61 C62 1.400(11) . ?
C66 C65 1.395(11) . ?
C66 H66 0.9300 . ?
C65 C64 1.370(12) . ?
C65 H65 0.9300 . ?
C64 C63 1.375(12) . ?
C64 H64 0.9300 . ?
C63 C62 1.368(11) . ?
C63 H63 0.9300 . ?
C62 H62 0.9300 . ?
C67 C72 1.387(9) . ?
C67 C68 1.398(10) . ?
C67 Bi4 2.258(7) . ?
C68 C69 1.386(10) . ?
C68 H68 0.9300 . ?
C69 C70 1.368(10) . ?
C69 H69 0.9300 . ?
C70 C71 1.390(10) . ?
C70 H70 0.9300 . ?
C71 C72 1.374(10) . ?
C71 H71 0.9300 . ?
C72 C73 1.517(10) . ?
C73 N4 1.473(8) . ?
C73 H73A 0.9700 . ?
C73 H73B 0.9700 . ?
C80 C79 1.387(10) . ?
C80 C75 1.402(10) . ?
C80 Bi4 2.225(7) . ?
C79 C78 1.393(10) . ?
C79 H79 0.9300 . ?
C78 C77 1.390(10) . ?
C78 H78 0.9300 . ?
C77 C76 1.376(10) . ?
C77 H77 0.9300 . ?
C76 C75 1.388(10) . ?
C76 H76 0.9300 . ?
C75 C74 1.503(9) . ?
C74 N4 1.479(9) . ?
C74 H74A 0.9700 . ?
C74 H74B 0.9700 . ?
C81 N4 1.480(9) . ?
C81 C82 1.535(9) . ?
C81 H81A 0.9700 . ?
C81 H81B 0.9700 . ?
C82 C83 1.509(10) . ?
C82 H82A 0.9700 . ?
C82 H82B 0.9700 . ?
C83 C88 1.374(10) . ?
C83 C84 1.377(11) . ?
C88 C87 1.381(11) . ?
C88 H88 0.9300 . ?
C87 C86 1.364(13) . ?
C87 H87 0.9300 . ?
C86 C85 1.387(12) . ?
C86 H86 0.9300 . ?
C85 C84 1.375(11) . ?
C85 H85 0.9300 . ?
C84 H84 0.9300 . ?
I1 Bi1 2.9890(6) . ?
I2 Bi2 2.9909(6) . ?
I3 Bi3 3.0043(6) . ?
I4 Bi4 2.9791(6) . ?
Bi1 N1 2.490(6) . ?
Bi2 N2 2.513(5) . ?
Bi3 N3 2.509(5) . ?
Bi4 N4 2.496(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
C2 C1 C6 119.8(7) . . ?
C2 C1 Bi1 126.1(5) . . ?
C6 C1 Bi1 114.0(5) . . ?
C3 C2 C1 119.6(7) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.4(7) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.2(7) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 121.7(7) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.2(7) . . ?
C5 C6 C7 120.7(6) . . ?
C1 C6 C7 120.0(6) . . ?
N1 C7 C6 109.6(6) . . ?
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 . . ?
C9 C14 C13 120.0(7) . . ?
C9 C14 Bi1 116.0(5) . . ?
C13 C14 Bi1 123.9(5) . . ?
C12 C13 C14 119.6(7) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C12 C11 121.1(8) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C11 C10 119.3(7) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C10 C9 120.6(7) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C9 C14 119.3(7) . . ?
C10 C9 C8 118.7(7) . . ?
C14 C9 C8 121.8(7) . . ?
N1 C8 C9 112.8(6) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C15 C16 116.1(6) . . ?
N1 C15 H15A 108.3 . . ?
C16 C15 H15A 108.3 . . ?
N1 C15 H15B 108.3 . . ?
C16 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C17 C16 C15 110.2(6) . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C22 117.0(8) . . ?
C18 C17 C16 121.4(7) . . ?
C22 C17 C16 121.6(7) . . ?
C19 C18 C17 121.8(7) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 120.9(8) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 118.4(8) . . ?
C19 C20 H20 120.8 . . ?
C21 C20 H20 120.8 . . ?
C22 C21 C20 121.0(8) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C17 120.8(8) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C28 C23 C24 119.1(7) . . ?
C28 C23 Bi2 115.3(5) . . ?
C24 C23 Bi2 125.6(5) . . ?
C25 C24 C23 120.3(7) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.7(7) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.5(7) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C28 120.2(7) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 119.1(7) . . ?
C27 C28 C29 121.3(6) . . ?
C23 C28 C29 119.6(6) . . ?
N2 C29 C28 108.7(5) . . ?
N2 C29 H29A 109.9 . . ?
C28 C29 H29A 109.9 . . ?
N2 C29 H29B 109.9 . . ?
C28 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
C35 C36 C31 118.9(7) . . ?
C35 C36 Bi2 124.7(5) . . ?
C31 C36 Bi2 116.3(5) . . ?
C36 C35 C34 120.9(7) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C33 C34 C35 119.0(7) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
C34 C33 C32 121.4(7) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C33 C32 C31 119.6(7) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C31 C36 120.2(7) . . ?
C32 C31 C30 119.1(7) . . ?
C36 C31 C30 120.5(7) . . ?
N2 C30 C31 112.4(6) . . ?
N2 C30 H30A 109.1 . . ?
C31 C30 H30A 109.1 . . ?
N2 C30 H30B 109.1 . . ?
C31 C30 H30B 109.1 . . ?
H30A C30 H30B 107.9 . . ?
N2 C37 C38 114.9(6) . . ?
N2 C37 H37B 108.5 . . ?
C38 C37 H37B 108.5 . . ?
N2 C37 H37A 108.5 . . ?
C38 C37 H37A 108.5 . . ?
H37B C37 H37A 107.5 . . ?
C39 C38 C37 112.1(7) . . ?
C39 C38 H38A 109.2 . . ?
C37 C38 H38A 109.2 . . ?
C39 C38 H38B 109.2 . . ?
C37 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?
C40 C39 C44 117.4(7) . . ?
C40 C39 C38 119.1(7) . . ?
C44 C39 C38 123.4(7) . . ?
C41 C40 C39 121.1(8) . . ?
C41 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C40 C41 C42 119.9(8) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
C43 C42 C41 119.9(8) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 120.4(8) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C43 C44 C39 121.1(8) . . ?
C43 C44 H44 119.4 . . ?
C39 C44 H44 119.4 . . ?
C57 C58 C53 119.2(7) . . ?
C57 C58 Bi3 125.3(5) . . ?
C53 C58 Bi3 115.4(5) . . ?
C58 C57 C56 120.7(7) . . ?
C58 C57 H57 119.7 . . ?
C56 C57 H57 119.7 . . ?
C55 C56 C57 119.9(7) . . ?
C55 C56 H56 120.0 . . ?
C57 C56 H56 120.0 . . ?
C56 C55 C54 118.8(7) . . ?
C56 C55 H55 120.6 . . ?
C54 C55 H55 120.6 . . ?
C53 C54 C55 121.4(7) . . ?
C53 C54 H54 119.3 . . ?
C55 C54 H54 119.3 . . ?
C54 C53 C58 120.0(7) . . ?
C54 C53 C52 120.5(7) . . ?
C58 C53 C52 119.5(7) . . ?
N3 C52 C53 109.2(6) . . ?
N3 C52 H52A 109.8 . . ?
C53 C52 H52A 109.8 . . ?
N3 C52 H52B 109.8 . . ?
C53 C52 H52B 109.8 . . ?
H52A C52 H52B 108.3 . . ?
C50 C45 C46 120.3(7) . . ?
C50 C45 Bi3 115.6(5) . . ?
C46 C45 Bi3 124.0(6) . . ?
C45 C46 C47 119.8(7) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 H46 120.1 . . ?
C48 C47 C46 119.9(7) . . ?
C48 C47 H47 120.1 . . ?
C46 C47 H47 120.1 . . ?
C49 C48 C47 120.6(8) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C48 C49 C50 119.1(8) . . ?
C48 C49 H49 120.5 . . ?
C50 C49 H49 120.5 . . ?
C45 C50 C49 120.2(7) . . ?
C45 C50 C51 121.4(7) . . ?
C49 C50 C51 118.1(7) . . ?
N3 C51 C50 112.3(6) . . ?
N3 C51 H51A 109.1 . . ?
C50 C51 H51A 109.1 . . ?
N3 C51 H51B 109.1 . . ?
C50 C51 H51B 109.1 . . ?
H51A C51 H51B 107.9 . . ?
N3 C59 C60 114.6(6) . . ?
N3 C59 H59B 108.6 . . ?
C60 C59 H59B 108.6 . . ?
N3 C59 H59A 108.6 . . ?
C60 C59 H59A 108.6 . . ?
H59B C59 H59A 107.6 . . ?
C61 C60 C59 113.9(7) . . ?
C61 C60 H60A 108.8 . . ?
C59 C60 H60A 108.8 . . ?
C61 C60 H60B 108.8 . . ?
C59 C60 H60B 108.8 . . ?
H60A C60 H60B 107.7 . . ?
C66 C61 C62 118.8(7) . . ?
C66 C61 C60 118.3(7) . . ?
C62 C61 C60 123.0(7) . . ?
C65 C66 C61 119.9(8) . . ?
C65 C66 H66 120.0 . . ?
C61 C66 H66 120.0 . . ?
C64 C65 C66 119.9(9) . . ?
C64 C65 H65 120.0 . . ?
C66 C65 H65 120.0 . . ?
C65 C64 C63 120.4(8) . . ?
C65 C64 H64 119.8 . . ?
C63 C64 H64 119.8 . . ?
C62 C63 C64 120.6(8) . . ?
C62 C63 H63 119.7 . . ?
C64 C63 H63 119.7 . . ?
C63 C62 C61 120.3(8) . . ?
C63 C62 H62 119.9 . . ?
C61 C62 H62 119.9 . . ?
C72 C67 C68 119.1(7) . . ?
C72 C67 Bi4 115.1(5) . . ?
C68 C67 Bi4 125.8(5) . . ?
C69 C68 C67 119.9(7) . . ?
C69 C68 H68 120.0 . . ?
C67 C68 H68 120.0 . . ?
C70 C69 C68 120.5(8) . . ?
C70 C69 H69 119.8 . . ?
C68 C69 H69 119.8 . . ?
C69 C70 C71 119.8(7) . . ?
C69 C70 H70 120.1 . . ?
C71 C70 H70 120.1 . . ?
C72 C71 C70 120.3(7) . . ?
C72 C71 H71 119.9 . . ?
C70 C71 H71 119.9 . . ?
C71 C72 C67 120.4(7) . . ?
C71 C72 C73 120.2(6) . . ?
C67 C72 C73 119.4(6) . . ?
N4 C73 C72 110.1(6) . . ?
N4 C73 H73A 109.6 . . ?
C72 C73 H73A 109.6 . . ?
N4 C73 H73B 109.6 . . ?
C72 C73 H73B 109.6 . . ?
H73A C73 H73B 108.2 . . ?
C79 C80 C75 119.6(7) . . ?
C79 C80 Bi4 124.0(5) . . ?
C75 C80 Bi4 116.4(5) . . ?
C80 C79 C78 120.9(7) . . ?
C80 C79 H79 119.6 . . ?
C78 C79 H79 119.6 . . ?
C77 C78 C79 119.0(7) . . ?
C77 C78 H78 120.5 . . ?
C79 C78 H78 120.5 . . ?
C76 C77 C78 120.5(7) . . ?
C76 C77 H77 119.8 . . ?
C78 C77 H77 119.8 . . ?
C77 C76 C75 120.9(7) . . ?
C77 C76 H76 119.5 . . ?
C75 C76 H76 119.5 . . ?
C76 C75 C80 119.1(7) . . ?
C76 C75 C74 119.9(7) . . ?
C80 C75 C74 120.9(7) . . ?
N4 C74 C75 112.4(6) . . ?
N4 C74 H74A 109.1 . . ?
C75 C74 H74A 109.1 . . ?
N4 C74 H74B 109.1 . . ?
C75 C74 H74B 109.1 . . ?
H74A C74 H74B 107.9 . . ?
N4 C81 C82 116.0(6) . . ?
N4 C81 H81A 108.3 . . ?
C82 C81 H81A 108.3 . . ?
N4 C81 H81B 108.3 . . ?
C82 C81 H81B 108.3 . . ?
H81A C81 H81B 107.4 . . ?
C83 C82 C81 110.9(6) . . ?
C83 C82 H82A 109.4 . . ?
C81 C82 H82A 109.5 . . ?
C83 C82 H82B 109.5 . . ?
C81 C82 H82B 109.5 . . ?
H82A C82 H82B 108.0 . . ?
C88 C83 C84 119.1(8) . . ?
C88 C83 C82 121.1(7) . . ?
C84 C83 C82 119.8(7) . . ?
C83 C88 C87 119.8(8) . . ?
C83 C88 H88 120.1 . . ?
C87 C88 H88 120.1 . . ?
C86 C87 C88 121.5(8) . . ?
C86 C87 H87 119.2 . . ?
C88 C87 H87 119.2 . . ?
C87 C86 C85 118.6(8) . . ?
C87 C86 H86 120.7 . . ?
C85 C86 H86 120.7 . . ?
C84 C85 C86 120.2(8) . . ?
C84 C85 H85 119.9 . . ?
C86 C85 H85 119.9 . . ?
C85 C84 C83 120.8(8) . . ?
C85 C84 H84 119.6 . . ?
C83 C84 H84 119.6 . . ?
C14 Bi1 C1 96.9(3) . . ?
C14 Bi1 N1 74.6(2) . . ?
C1 Bi1 N1 72.6(2) . . ?
C14 Bi1 I1 93.07(18) . . ?
C1 Bi1 I1 93.93(18) . . ?
N1 Bi1 I1 160.08(14) . . ?
C36 Bi2 C23 97.1(3) . . ?
C36 Bi2 N2 73.9(2) . . ?
C23 Bi2 N2 71.6(2) . . ?
C36 Bi2 I2 91.45(18) . . ?
C23 Bi2 I2 93.87(18) . . ?
N2 Bi2 I2 157.44(14) . . ?
C58 Bi3 C45 96.8(3) . . ?
C58 Bi3 N3 71.8(2) . . ?
C45 Bi3 N3 74.3(2) . . ?
C58 Bi3 I3 94.47(18) . . ?
C45 Bi3 I3 90.82(18) . . ?
N3 Bi3 I3 157.94(13) . . ?
C80 Bi4 C67 98.9(3) . . ?
C80 Bi4 N4 74.3(2) . . ?
C67 Bi4 N4 72.0(2) . . ?
C80 Bi4 I4 92.49(17) . . ?
C67 Bi4 I4 93.45(18) . . ?
N4 Bi4 I4 158.05(14) . . ?
C15 N1 C7 114.5(6) . . ?
C15 N1 C8 113.1(6) . . ?
C7 N1 C8 111.9(6) . . ?
C15 N1 Bi1 106.2(4) . . ?
C7 N1 Bi1 103.1(4) . . ?
C8 N1 Bi1 107.1(4) . . ?
C29 N2 C30 110.6(6) . . ?
C29 N2 C37 115.0(5) . . ?
C30 N2 C37 108.8(6) . . ?
C29 N2 Bi2 103.2(4) . . ?
C30 N2 Bi2 105.7(4) . . ?
C37 N2 Bi2 113.0(4) . . ?
C52 N3 C51 110.3(6) . . ?
C52 N3 C59 115.4(5) . . ?
C51 N3 C59 108.5(6) . . ?
C52 N3 Bi3 102.9(4) . . ?
C51 N3 Bi3 105.5(4) . . ?
C59 N3 Bi3 113.6(4) . . ?
C73 N4 C74 112.4(6) . . ?
C73 N4 C81 114.3(5) . . ?
C74 N4 C81 112.4(6) . . ?
C73 N4 Bi4 103.2(4) . . ?
C74 N4 Bi4 106.5(4) . . ?
C81 N4 Bi4 107.2(4) . . ?

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 0.2(11) . . . . ?
Bi1 C1 C2 C3 -179.1(6) . . . . ?
C1 C2 C3 C4 0.3(12) . . . . ?
C2 C3 C4 C5 -0.3(12) . . . . ?
C3 C4 C5 C6 -0.2(12) . . . . ?
C4 C5 C6 C1 0.7(11) . . . . ?
C4 C5 C6 C7 -178.3(7) . . . . ?
C2 C1 C6 C5 -0.7(11) . . . . ?
Bi1 C1 C6 C5 178.7(6) . . . . ?
C2 C1 C6 C7 178.3(7) . . . . ?
Bi1 C1 C6 C7 -2.3(8) . . . . ?
C5 C6 C7 N1 145.3(7) . . . . ?
C1 C6 C7 N1 -33.7(9) . . . . ?
C9 C14 C13 C12 -1.0(11) . . . . ?
Bi1 C14 C13 C12 179.0(6) . . . . ?
C14 C13 C12 C11 2.0(12) . . . . ?
C13 C12 C11 C10 -1.6(12) . . . . ?
C12 C11 C10 C9 0.2(12) . . . . ?
C11 C10 C9 C14 0.8(12) . . . . ?
C11 C10 C9 C8 175.9(7) . . . . ?
C13 C14 C9 C10 -0.4(11) . . . . ?
Bi1 C14 C9 C10 179.6(6) . . . . ?
C13 C14 C9 C8 -175.3(7) . . . . ?
Bi1 C14 C9 C8 4.6(9) . . . . ?
C10 C9 C8 N1 159.6(7) . . . . ?
C14 C9 C8 N1 -25.5(10) . . . . ?
N1 C15 C16 C17 177.9(6) . . . . ?
C15 C16 C17 C18 68.2(9) . . . . ?
C15 C16 C17 C22 -110.4(8) . . . . ?
C22 C17 C18 C19 1.2(11) . . . . ?
C16 C17 C18 C19 -177.4(6) . . . . ?
C17 C18 C19 C20 -1.7(11) . . . . ?
C18 C19 C20 C21 1.3(11) . . . . ?
C19 C20 C21 C22 -0.4(11) . . . . ?
C20 C21 C22 C17 -0.1(11) . . . . ?
C18 C17 C22 C21 -0.3(11) . . . . ?
C16 C17 C22 C21 178.3(7) . . . . ?
C28 C23 C24 C25 -0.8(12) . . . . ?
Bi2 C23 C24 C25 -179.2(6) . . . . ?
C23 C24 C25 C26 2.5(12) . . . . ?
C24 C25 C26 C27 -2.8(12) . . . . ?
C25 C26 C27 C28 1.4(12) . . . . ?
C26 C27 C28 C23 0.2(12) . . . . ?
C26 C27 C28 C29 179.5(7) . . . . ?
C24 C23 C28 C27 -0.5(11) . . . . ?
Bi2 C23 C28 C27 178.0(6) . . . . ?
C24 C23 C28 C29 -179.8(7) . . . . ?
Bi2 C23 C28 C29 -1.3(9) . . . . ?
C27 C28 C29 N2 145.5(7) . . . . ?
C23 C28 C29 N2 -35.1(9) . . . . ?
C31 C36 C35 C34 -1.4(11) . . . . ?
Bi2 C36 C35 C34 176.5(6) . . . . ?
C36 C35 C34 C33 1.1(12) . . . . ?
C35 C34 C33 C32 -0.3(11) . . . . ?
C34 C33 C32 C31 -0.2(11) . . . . ?
C33 C32 C31 C36 -0.1(11) . . . . ?
C33 C32 C31 C30 175.3(6) . . . . ?
C35 C36 C31 C32 0.9(11) . . . . ?
Bi2 C36 C31 C32 -177.1(5) . . . . ?
C35 C36 C31 C30 -174.5(7) . . . . ?
Bi2 C36 C31 C30 7.5(9) . . . . ?
C32 C31 C30 N2 152.6(6) . . . . ?
C36 C31 C30 N2 -32.0(9) . . . . ?
N2 C37 C38 C39 -169.5(6) . . . . ?
C37 C38 C39 C40 149.7(7) . . . . ?
C37 C38 C39 C44 -31.0(10) . . . . ?
C44 C39 C40 C41 1.7(10) . . . . ?
C38 C39 C40 C41 -179.0(7) . . . . ?
C39 C40 C41 C42 -0.4(11) . . . . ?
C40 C41 C42 C43 -1.0(11) . . . . ?
C41 C42 C43 C44 1.0(12) . . . . ?
C42 C43 C44 C39 0.3(12) . . . . ?
C40 C39 C44 C43 -1.6(11) . . . . ?
C38 C39 C44 C43 179.1(7) . . . . ?
C53 C58 C57 C56 1.9(12) . . . . ?
Bi3 C58 C57 C56 -179.7(6) . . . . ?
C58 C57 C56 C55 -2.4(12) . . . . ?
C57 C56 C55 C54 1.7(12) . . . . ?
C56 C55 C54 C53 -0.7(12) . . . . ?
C55 C54 C53 C58 0.3(12) . . . . ?
C55 C54 C53 C52 179.8(7) . . . . ?
C57 C58 C53 C54 -0.9(11) . . . . ?
Bi3 C58 C53 C54 -179.4(6) . . . . ?
C57 C58 C53 C52 179.5(7) . . . . ?
Bi3 C58 C53 C52 1.0(9) . . . . ?
C54 C53 C52 N3 -144.3(7) . . . . ?
C58 C53 C52 N3 35.3(9) . . . . ?
C50 C45 C46 C47 0.9(11) . . . . ?
Bi3 C45 C46 C47 -176.3(6) . . . . ?
C45 C46 C47 C48 -0.9(11) . . . . ?
C46 C47 C48 C49 0.3(12) . . . . ?
C47 C48 C49 C50 0.2(11) . . . . ?
C46 C45 C50 C49 -0.3(11) . . . . ?
Bi3 C45 C50 C49 177.1(6) . . . . ?
C46 C45 C50 C51 174.3(7) . . . . ?
Bi3 C45 C50 C51 -8.3(9) . . . . ?
C48 C49 C50 C45 -0.2(11) . . . . ?
C48 C49 C50 C51 -175.0(7) . . . . ?
C45 C50 C51 N3 32.1(9) . . . . ?
C49 C50 C51 N3 -153.1(7) . . . . ?
N3 C59 C60 C61 167.6(6) . . . . ?
C59 C60 C61 C66 -152.7(7) . . . . ?
C59 C60 C61 C62 27.3(10) . . . . ?
C62 C61 C66 C65 -1.8(10) . . . . ?
C60 C61 C66 C65 178.2(6) . . . . ?
C61 C66 C65 C64 0.3(11) . . . . ?
C66 C65 C64 C63 0.5(12) . . . . ?
C65 C64 C63 C62 0.3(12) . . . . ?
C64 C63 C62 C61 -1.9(12) . . . . ?
C66 C61 C62 C63 2.7(11) . . . . ?
C60 C61 C62 C63 -177.4(7) . . . . ?
C72 C67 C68 C69 -0.1(11) . . . . ?
Bi4 C67 C68 C69 -176.8(6) . . . . ?
C67 C68 C69 C70 1.1(12) . . . . ?
C68 C69 C70 C71 -2.4(12) . . . . ?
C69 C70 C71 C72 2.8(12) . . . . ?
C70 C71 C72 C67 -1.9(12) . . . . ?
C70 C71 C72 C73 -179.7(7) . . . . ?
C68 C67 C72 C71 0.5(11) . . . . ?
Bi4 C67 C72 C71 177.6(6) . . . . ?
C68 C67 C72 C73 178.4(7) . . . . ?
Bi4 C67 C72 C73 -4.5(9) . . . . ?
C71 C72 C73 N4 146.0(7) . . . . ?
C67 C72 C73 N4 -31.9(9) . . . . ?
C75 C80 C79 C78 -1.6(11) . . . . ?
Bi4 C80 C79 C78 176.8(6) . . . . ?
C80 C79 C78 C77 1.7(11) . . . . ?
C79 C78 C77 C76 -0.5(11) . . . . ?
C78 C77 C76 C75 -0.7(12) . . . . ?
C77 C76 C75 C80 0.7(11) . . . . ?
C77 C76 C75 C74 178.0(7) . . . . ?
C79 C80 C75 C76 0.4(11) . . . . ?
Bi4 C80 C75 C76 -178.1(6) . . . . ?
C79 C80 C75 C74 -176.8(7) . . . . ?
Bi4 C80 C75 C74 4.7(9) . . . . ?
C76 C75 C74 N4 155.0(7) . . . . ?
C80 C75 C74 N4 -27.8(9) . . . . ?
N4 C81 C82 C83 176.4(6) . . . . ?
C81 C82 C83 C88 -112.2(8) . . . . ?
C81 C82 C83 C84 67.1(9) . . . . ?
C84 C83 C88 C87 -1.1(11) . . . . ?
C82 C83 C88 C87 178.2(7) . . . . ?
C83 C88 C87 C86 0.1(12) . . . . ?
C88 C87 C86 C85 0.7(12) . . . . ?
C87 C86 C85 C84 -0.7(12) . . . . ?
C86 C85 C84 C83 -0.3(11) . . . . ?
C88 C83 C84 C85 1.2(11) . . . . ?
C82 C83 C84 C85 -178.1(6) . . . . ?
C16 C15 N1 C7 54.2(9) . . . . ?
C16 C15 N1 C8 -75.5(8) . . . . ?
C16 C15 N1 Bi1 167.3(5) . . . . ?
C6 C7 N1 C15 161.3(6) . . . . ?
C6 C7 N1 C8 -68.4(7) . . . . ?
C6 C7 N1 Bi1 46.3(6) . . . . ?
C9 C8 N1 C15 -87.0(7) . . . . ?
C9 C8 N1 C7 141.9(6) . . . . ?
C9 C8 N1 Bi1 29.6(7) . . . . ?
C28 C29 N2 C30 -65.3(7) . . . . ?
C28 C29 N2 C37 171.0(6) . . . . ?
C28 C29 N2 Bi2 47.4(6) . . . . ?
C31 C30 N2 C29 146.7(6) . . . . ?
C31 C30 N2 C37 -86.1(7) . . . . ?
C31 C30 N2 Bi2 35.6(6) . . . . ?
C38 C37 N2 C29 -49.5(8) . . . . ?
C38 C37 N2 C30 -174.2(6) . . . . ?
C38 C37 N2 Bi2 68.7(7) . . . . ?
C53 C52 N3 C51 64.9(7) . . . . ?
C53 C52 N3 C59 -171.6(6) . . . . ?
C53 C52 N3 Bi3 -47.3(6) . . . . ?
C50 C51 N3 C52 -145.3(6) . . . . ?
C50 C51 N3 C59 87.3(7) . . . . ?
C50 C51 N3 Bi3 -34.8(6) . . . . ?
C60 C59 N3 C52 51.7(9) . . . . ?
C60 C59 N3 C51 176.1(6) . . . . ?
C60 C59 N3 Bi3 -66.9(7) . . . . ?
C72 C73 N4 C74 -68.5(7) . . . . ?
C72 C73 N4 C81 161.9(6) . . . . ?
C72 C73 N4 Bi4 45.8(6) . . . . ?
C75 C74 N4 C73 144.9(6) . . . . ?
C75 C74 N4 C81 -84.5(7) . . . . ?
C75 C74 N4 Bi4 32.7(6) . . . . ?
C82 C81 N4 C73 51.2(9) . . . . ?
C82 C81 N4 C74 -78.4(8) . . . . ?
C82 C81 N4 Bi4 164.8(5) . . . . ?

_refine_diff_density_max         1.983
_refine_diff_density_min         -1.702
_refine_diff_density_rms         0.217

####################################################################### 
# 
# 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_platon_sq
_database_code_depnum_ccdc_archive 'CCDC 1520823'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-20 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         'C17 H19 Bi F N O'
_chemical_formula_sum            'C17 H19 Bi F N O'
_chemical_formula_weight         481.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   12.506(7)
_cell_length_b                   8.658(5)
_cell_length_c                   18.119(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.129(9)
_cell_angle_gamma                90
_cell_volume                     1842.0(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    297
_cell_measurement_reflns_used    4634
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      20.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    9.579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.447766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; SADABS - V2.03 (Bruker 2001)was used for absorption 
correction. R(int) =  0.1461 before parameter refinement
 and  0.0619 after parameter refinement. Ratio of minimum 
to maximum apparent transmission:  0.447766
 Lambda/2 correction factor = 0.0015
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297
_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            17537
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.394
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_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             3425
_reflns_number_gt                2761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0296P)²+1.5568P] 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         3425
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.66483(2) 0.08456(3) 0.27982(2) 0.03784(11) Uani 1 1 d . . . . .
C1 C 0.7720(6) 0.1853(9) 0.3953(4) 0.0374(17) Uani 1 1 d . . . . .
C6 C 0.8207(6) 0.0887(9) 0.4582(4) 0.0435(18) Uani 1 1 d . . . . .
C5 C 0.8918(7) 0.1469(10) 0.5285(5) 0.058(2) Uani 1 1 d . . . . .
H5 H 0.9235 0.0800 0.5705 0.069 Uiso 1 1 calc R U . . .
C4 C 0.9170(7) 0.2997(10) 0.5381(5) 0.059(2) Uani 1 1 d . . . . .
H4 H 0.9665 0.3368 0.5858 0.071 Uiso 1 1 calc R U . . .
C3 C 0.8684(7) 0.3988(10) 0.4764(5) 0.053(2) Uani 1 1 d . . . . .
H3 H 0.8831 0.5041 0.4827 0.063 Uiso 1 1 calc R U . . .
C2 C 0.7973(6) 0.3418(9) 0.4046(4) 0.0412(18) Uani 1 1 d . . . . .
H2 H 0.7664 0.4088 0.3625 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8007(7) -0.0831(9) 0.4479(5) 0.057(2) Uani 1 1 d . . . . .
H7A H 0.8584 -0.1289 0.4301 0.068 Uiso 1 1 calc R U . . .
H7B H 0.8072 -0.1293 0.4980 0.068 Uiso 1 1 calc R U . . .
C14 C 0.5005(6) 0.0813(9) 0.3024(4) 0.0411(18) Uani 1 1 d . . . . .
C9 C 0.4903(6) -0.0089(9) 0.3634(4) 0.0401(19) Uani 1 1 d . . . . .
C10 C 0.3864(7) -0.0340(10) 0.3711(5) 0.054(2) Uani 1 1 d . . . . .
H10 H 0.3807 -0.0972 0.4111 0.064 Uiso 1 1 calc R U . . .
C11 C 0.2896(9) 0.0355(12) 0.3188(7) 0.080(3) Uani 1 1 d . . . . .
H11 H 0.2186 0.0168 0.3228 0.096 Uiso 1 1 calc R U . . .
C12 C 0.2993(8) 0.1324(12) 0.2608(7) 0.073(3) Uani 1 1 d . . . . .
H12 H 0.2354 0.1837 0.2278 0.088 Uiso 1 1 calc R U . . .
C13 C 0.4027(7) 0.1532(10) 0.2518(5) 0.054(2) Uani 1 1 d . . . . .
H13 H 0.4079 0.2160 0.2115 0.065 Uiso 1 1 calc R U . . .
C8 C 0.5964(7) -0.0734(8) 0.4230(4) 0.046(2) Uani 1 1 d . . . . .
H8A H 0.6277 0.0026 0.4641 0.055 Uiso 1 1 calc R U . . .
H8B H 0.5765 -0.1641 0.4469 0.055 Uiso 1 1 calc R U . . .
C15 C 0.6772(7) -0.2798(8) 0.3668(5) 0.053(2) Uani 1 1 d . . . . .
H15A H 0.6785 -0.3421 0.4116 0.063 Uiso 1 1 calc R U . . .
H15B H 0.7435 -0.3071 0.3534 0.063 Uiso 1 1 calc R U . . .
C16 C 0.5721(8) -0.3176(9) 0.2987(5) 0.056(2) Uani 1 1 d . . . . .
H16A H 0.5693 -0.4276 0.2880 0.067 Uiso 1 1 calc R U . . .
H16B H 0.5050 -0.2900 0.3111 0.067 Uiso 1 1 calc R U . . .
C17 C 0.4730(8) -0.2523(14) 0.1667(5) 0.094(4) Uani 1 1 d . . . . .
H17A H 0.4824 -0.2020 0.1221 0.141 Uiso 1 1 calc R U . . .
H17B H 0.4103 -0.2065 0.1778 0.141 Uiso 1 1 calc R U . . .
H17C H 0.4581 -0.3601 0.1554 0.141 Uiso 1 1 calc R U . . .
F1 F 0.6199(4) 0.3158(5) 0.2261(2) 0.0516(11) Uani 1 1 d . . . . .
N1 N 0.6850(5) -0.1162(6) 0.3893(3) 0.0390(15) Uani 1 1 d . . . . .
O1 O 0.5737(5) -0.2353(7) 0.2327(3) 0.0616(16) 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 F1 2.213(4) . ?
Bi1 C14 2.229(7) . ?
Bi1 C1 2.237(7) . ?
Bi1 N1 2.583(6) . ?
C1 C6 1.376(9) . ?
C1 C2 1.388(10) . ?
C6 C5 1.373(11) . ?
C6 C7 1.509(10) . ?
C5 C4 1.357(12) . ?
C5 H5 0.9300 . ?
C4 C3 1.374(11) . ?
C4 H4 0.9300 . ?
C3 C2 1.389(10) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 N1 1.498(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C9 1.394(10) . ?
C14 C13 1.397(11) . ?
C9 C10 1.372(10) . ?
C9 C8 1.501(10) . ?
C10 C11 1.392(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(12) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C8 N1 1.485(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 N1 1.468(9) . ?
C15 C16 1.497(11) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.399(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O1 1.415(10) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 Bi1 C14 88.9(2) . . ?
F1 Bi1 C1 92.2(2) . . ?
C14 Bi1 C1 97.3(3) . . ?
F1 Bi1 N1 152.82(17) . . ?
C14 Bi1 N1 72.8(2) . . ?
C1 Bi1 N1 71.1(2) . . ?
C6 C1 C2 118.4(7) . . ?
C6 C1 Bi1 119.3(5) . . ?
C2 C1 Bi1 122.2(5) . . ?
C5 C6 C1 120.4(8) . . ?
C5 C6 C7 120.2(7) . . ?
C1 C6 C7 119.3(7) . . ?
C4 C5 C6 121.6(8) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C4 C3 119.1(8) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C3 C2 120.1(8) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 120.0 . . ?
C1 C2 C3 120.4(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
N1 C7 C6 110.8(6) . . ?
N1 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C14 C13 118.1(7) . . ?
C9 C14 Bi1 119.6(5) . . ?
C13 C14 Bi1 121.9(6) . . ?
C10 C9 C14 121.2(8) . . ?
C10 C9 C8 120.1(8) . . ?
C14 C9 C8 118.6(7) . . ?
C9 C10 C11 119.6(8) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.8(9) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.3(9) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.8(9) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
N1 C8 C9 113.4(6) . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
N1 C15 C16 113.3(7) . . ?
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 . . ?
O1 C16 C15 109.0(7) . . ?
O1 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
O1 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 N1 C8 111.5(6) . . ?
C15 N1 C7 109.7(6) . . ?
C8 N1 C7 109.7(6) . . ?
C15 N1 Bi1 117.1(5) . . ?
C8 N1 Bi1 105.0(4) . . ?
C7 N1 Bi1 103.3(4) . . ?
C16 O1 C17 113.5(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 0.5(12) . . . . ?
Bi1 C1 C6 C5 176.4(6) . . . . ?
C2 C1 C6 C7 -176.0(7) . . . . ?
Bi1 C1 C6 C7 -0.1(10) . . . . ?
C1 C6 C5 C4 -0.6(14) . . . . ?
C7 C6 C5 C4 175.9(8) . . . . ?
C6 C5 C4 C3 1.3(14) . . . . ?
C5 C4 C3 C2 -2.0(13) . . . . ?
C6 C1 C2 C3 -1.3(11) . . . . ?
Bi1 C1 C2 C3 -177.0(5) . . . . ?
C4 C3 C2 C1 2.0(12) . . . . ?
C5 C6 C7 N1 151.1(7) . . . . ?
C1 C6 C7 N1 -32.3(10) . . . . ?
C13 C14 C9 C10 3.7(11) . . . . ?
Bi1 C14 C9 C10 -169.2(5) . . . . ?
C13 C14 C9 C8 -173.8(6) . . . . ?
Bi1 C14 C9 C8 13.3(8) . . . . ?
C14 C9 C10 C11 -2.1(12) . . . . ?
C8 C9 C10 C11 175.4(7) . . . . ?
C9 C10 C11 C12 -1.7(14) . . . . ?
C10 C11 C12 C13 3.8(15) . . . . ?
C11 C12 C13 C14 -2.1(14) . . . . ?
C9 C14 C13 C12 -1.6(11) . . . . ?
Bi1 C14 C13 C12 171.1(6) . . . . ?
C10 C9 C8 N1 147.7(7) . . . . ?
C14 C9 C8 N1 -34.8(9) . . . . ?
N1 C15 C16 O1 62.4(9) . . . . ?
C16 C15 N1 C8 68.0(8) . . . . ?
C16 C15 N1 C7 -170.3(7) . . . . ?
C16 C15 N1 Bi1 -53.0(8) . . . . ?
C9 C8 N1 C15 -93.7(7) . . . . ?
C9 C8 N1 C7 144.5(6) . . . . ?
C9 C8 N1 Bi1 34.1(7) . . . . ?
C6 C7 N1 C15 167.2(7) . . . . ?
C6 C7 N1 C8 -70.0(8) . . . . ?
C6 C7 N1 Bi1 41.5(7) . . . . ?
C15 C16 O1 C17 -174.7(7) . . . . ?

_refine_diff_density_max         0.988
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.131



