# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_180315-1
_database_code_depnum_ccdc_archive 'CCDC 1937537'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2019-06-30
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C56 H40 Bi2 N12, 0.5(C14 H16)'
_chemical_formula_sum            'C63 H48 Bi2 N12'
_chemical_formula_weight         1391.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.8511(3)
_cell_length_b                   11.8616(4)
_cell_length_c                   14.2639(4)
_cell_angle_alpha                97.805(3)
_cell_angle_beta                 104.276(3)
_cell_angle_gamma                107.123(3)
_cell_volume                     1351.40(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    13368
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9310
_cell_measurement_theta_min      3.3250
_exptl_absorpt_coefficient_mu    6.395
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30468
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.80
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0251
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.8515
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  32.00   1.00   20.13    --   15.53 -57.00 -90.00   84
  2  ω    -52.00  32.00   1.00   20.13    --   15.53 -57.00 150.00   84
  3  ω    -67.00   9.00   1.00   20.13    --  -17.17 118.00 -42.72   76
  4  ω    -85.00  10.00   1.00   20.13    --  -17.17 -77.00-180.00   95
  5  ω    -84.00   0.00   1.00   20.13    --  -17.17 -57.00 -90.00   84
  6  ω    -34.00  50.00   1.00   20.13    --  -17.17  58.00  67.00   84
  7  ω    -85.00  10.00   1.00   20.13    --  -17.17 -77.00  30.00   95
  8  ω    -84.00   0.00   1.00   20.13    --  -17.17 -57.00 120.00   84
  9  ω    -74.00  -1.00   1.00   20.13    --  -17.17 130.00  28.07   73
 10  ω    -67.00   9.00   1.00   20.13    --  -17.17 118.00 174.86   76
 11  ω     35.00  88.00   1.00   20.13    --   15.53 178.00 120.00   53
 12  ω    -55.00  27.00   1.00   20.13    --  -17.17  97.00 101.66   82
 13  ω    -75.00  -2.00   1.00   20.13    --  -17.17 133.00 -90.97   73
 14  ω    -44.00  50.00   1.00   20.13    --  -17.17  77.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0460428000
_diffrn_orient_matrix_UB_12      -0.0227232000
_diffrn_orient_matrix_UB_13      0.0361269000
_diffrn_orient_matrix_UB_21      -0.0742467000
_diffrn_orient_matrix_UB_22      -0.0455622000
_diffrn_orient_matrix_UB_23      -0.0018447000
_diffrn_orient_matrix_UB_31      0.0103974000
_diffrn_orient_matrix_UB_32      -0.0391379000
_diffrn_orient_matrix_UB_33      -0.0382720000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4515
_reflns_number_total             5135
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5135
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0221P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0510
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C32-C31
 1.53 with sigma of 0.01
 C30-C29 = C29-C31 = C33-C31 = C34-C33 = C35-C34 = C35-C30
 1.42 with sigma of 0.01
 C32-C29 \\sim C32-C33
 with sigma of 0.01
3. Restrained planarity
 C29, C30, C31, C32, C33, C34, C35
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
5. Others
 Fixed Sof: C29(0.5) H29(0.5) C32(0.5) H32A(0.5) H32B(0.5) H32C(0.5) C31(0.5)
 C30(0.5) H30(0.5) C33(0.5) H33(0.5) C34(0.5) H34(0.5) C35(0.5) H35(0.5)
6.a Riding coordinates:
 C29(H29), C32(H32A,H32B,H32C), C30(H30), C33(H33), C34(H34), C35(H35)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C24(H24),
  C25(H25), C26(H26), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.498219(19) 0.382689(12) 0.457080(11) 0.02904(6) Uani 1 1 d . . .
C1 C 0.1253(5) 0.7153(4) 0.4991(3) 0.0415(11) Uani 1 1 d . . .
H1 H 0.1928 0.7004 0.5538 0.050 Uiso 1 1 calc R . .
C2 C 0.0988(6) 0.8245(4) 0.5055(4) 0.0497(12) Uani 1 1 d . . .
H2 H 0.1483 0.8834 0.5644 0.060 Uiso 1 1 calc R . .
C3 C -0.0014(6) 0.8460(4) 0.4243(4) 0.0601(14) Uani 1 1 d . . .
H3 H -0.0183 0.9200 0.4284 0.072 Uiso 1 1 calc R . .
C4 C -0.0761(6) 0.7591(4) 0.3377(4) 0.0570(14) Uani 1 1 d . . .
H4 H -0.1441 0.7742 0.2833 0.068 Uiso 1 1 calc R . .
C5 C -0.0508(5) 0.6500(4) 0.3309(4) 0.0461(11) Uani 1 1 d . . .
H5 H -0.1027 0.5910 0.2722 0.055 Uiso 1 1 calc R . .
C6 C 0.0512(5) 0.6273(4) 0.4110(3) 0.0363(10) Uani 1 1 d . . .
C7 C 0.0850(5) 0.5126(3) 0.3985(3) 0.0351(10) Uani 1 1 d . . .
C8 C 0.0759(5) 0.3394(3) 0.3356(3) 0.0341(10) Uani 1 1 d . . .
C9 C 0.0270(5) 0.2221(3) 0.2661(3) 0.0377(10) Uani 1 1 d . . .
C10 C 0.0879(5) 0.1316(4) 0.2924(3) 0.0453(11) Uani 1 1 d . . .
H10 H 0.1567 0.1429 0.3563 0.054 Uiso 1 1 calc R . .
C11 C 0.0461(6) 0.0240(4) 0.2231(4) 0.0557(13) Uani 1 1 d . . .
H11 H 0.0874 -0.0363 0.2405 0.067 Uiso 1 1 calc R . .
C12 C -0.0555(7) 0.0076(4) 0.1300(4) 0.0647(15) Uani 1 1 d . . .
H12 H -0.0823 -0.0638 0.0835 0.078 Uiso 1 1 calc R . .
C13 C -0.1186(7) 0.0952(4) 0.1040(4) 0.0667(15) Uani 1 1 d . . .
H13 H -0.1897 0.0822 0.0404 0.080 Uiso 1 1 calc R . .
C14 C -0.0774(6) 0.2032(4) 0.1717(3) 0.0521(12) Uani 1 1 d . . .
H14 H -0.1200 0.2626 0.1535 0.062 Uiso 1 1 calc R . .
C15 C 0.4241(6) 0.2805(4) 0.1732(3) 0.0450(11) Uani 1 1 d . . .
H15 H 0.3715 0.2681 0.2218 0.054 Uiso 1 1 calc R . .
C16 C 0.4166(6) 0.1828(4) 0.1063(3) 0.0525(13) Uani 1 1 d . . .
H16 H 0.3610 0.1046 0.1103 0.063 Uiso 1 1 calc R . .
C17 C 0.4917(7) 0.2011(4) 0.0332(3) 0.0561(14) Uani 1 1 d . . .
H17 H 0.4870 0.1350 -0.0122 0.067 Uiso 1 1 calc R . .
C18 C 0.5734(6) 0.3161(4) 0.0269(3) 0.0579(14) Uani 1 1 d . . .
H18 H 0.6233 0.3278 -0.0229 0.070 Uiso 1 1 calc R . .
C19 C 0.5820(6) 0.4148(4) 0.0942(3) 0.0478(12) Uani 1 1 d . . .
H19 H 0.6364 0.4928 0.0894 0.057 Uiso 1 1 calc R . .
C20 C 0.5089(5) 0.3970(3) 0.1693(3) 0.0358(10) Uani 1 1 d . . .
C21 C 0.5141(5) 0.5023(3) 0.2396(3) 0.0324(9) Uani 1 1 d . . .
C22 C 0.5132(5) 0.6747(3) 0.2986(3) 0.0336(10) Uani 1 1 d . . .
C23 C 0.5083(5) 0.7981(3) 0.3052(3) 0.0351(10) Uani 1 1 d . . .
C24 C 0.5751(6) 0.8687(4) 0.2455(3) 0.0434(11) Uani 1 1 d . . .
H24 H 0.6252 0.8384 0.2028 0.052 Uiso 1 1 calc R . .
C25 C 0.5672(6) 0.9832(4) 0.2495(4) 0.0523(13) Uani 1 1 d . . .
H25 H 0.6149 1.0309 0.2106 0.063 Uiso 1 1 calc R . .
C26 C 0.4904(6) 1.0274(4) 0.3096(4) 0.0554(13) Uani 1 1 d . . .
H26 H 0.4832 1.1042 0.3102 0.066 Uiso 1 1 calc R . .
C27 C 0.4233(6) 0.9595(4) 0.3694(4) 0.0558(13) Uani 1 1 d . . .
H27 H 0.3727 0.9907 0.4113 0.067 Uiso 1 1 calc R . .
C28 C 0.4314(6) 0.8444(4) 0.3671(3) 0.0456(11) Uani 1 1 d . . .
H28 H 0.3851 0.7979 0.4070 0.055 Uiso 1 1 calc R . .
N1 N 0.2111(4) 0.3821(3) 0.4148(2) 0.0344(8) Uani 1 1 d . . .
N2 N 0.2167(4) 0.4960(3) 0.4559(2) 0.0336(8) Uani 1 1 d . . .
N3 N -0.0078(4) 0.4173(3) 0.3220(3) 0.0396(9) Uani 1 1 d . . .
N4 N 0.5052(4) 0.5006(3) 0.3313(2) 0.0330(8) Uani 1 1 d . . .
N5 N 0.5052(4) 0.6137(3) 0.3697(2) 0.0357(8) Uani 1 1 d . . .
N6 N 0.5205(4) 0.6091(3) 0.2161(2) 0.0366(8) Uani 1 1 d . . .
C29 C 0.9027(18) 0.5260(12) 0.9229(11) 0.113(4) Uani 0.50 1 d PDU . .
H29 H 0.8410 0.5697 0.8877 0.135 Uiso 0.50 1 d PR . .
C32 C 0.9889(18) 0.6912(12) 1.0708(12) 0.137(5) Uani 0.50 1 d PDU . .
H32A H 1.0562 0.7126 1.1389 0.206 Uiso 0.50 1 d PR . .
H32B H 1.0322 0.7526 1.0374 0.206 Uiso 0.50 1 d PR . .
H32C H 0.8771 0.6848 1.0678 0.206 Uiso 0.50 1 d PR . .
C31 C 0.9930(15) 0.5712(11) 1.0220(11) 0.120(4) Uani 0.50 1 d PDU . .
C30 C 0.8996(18) 0.4150(13) 0.8716(13) 0.117(4) Uani 0.50 1 d PDU . .
H30 H 0.8373 0.3826 0.8028 0.141 Uiso 0.50 1 d PR . .
C33 C 1.0853(19) 0.5160(12) 1.0791(15) 0.121(4) Uani 0.50 1 d PDU . .
H33 H 1.1475 0.5482 1.1479 0.145 Uiso 0.50 1 d PR . .
C34 C 1.0842(19) 0.4064(13) 1.0294(14) 0.124(4) Uani 0.50 1 d PDU . .
H34 H 1.1469 0.3630 1.0643 0.149 Uiso 0.50 1 d PR . .
C35 C 0.9914(18) 0.3611(15) 0.9293(14) 0.125(4) Uani 0.50 1 d PDU . .
H35 H 0.9909 0.2846 0.8968 0.149 Uiso 0.50 1 d PR . .


_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 Bi1 2.8721(3) 2_666 ?
Bi1 N1 2.461(3) . ?
Bi1 N2 2.411(3) 2_666 ?
Bi1 N4 2.422(3) . ?
Bi1 N5 2.473(3) 2_666 ?
C1 H1 0.9300 . ?
C1 C2 1.378(6) . ?
C1 C6 1.391(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(6) . ?
C6 C7 1.474(5) . ?
C7 N2 1.332(5) . ?
C7 N3 1.349(5) . ?
C8 C9 1.471(5) . ?
C8 N1 1.337(5) . ?
C8 N3 1.349(5) . ?
C9 C10 1.391(6) . ?
C9 C14 1.378(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.359(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.372(5) . ?
C15 C20 1.380(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(6) . ?
C20 C21 1.473(5) . ?
C21 N4 1.332(5) . ?
C21 N6 1.343(5) . ?
C22 C23 1.468(5) . ?
C22 N5 1.328(5) . ?
C22 N6 1.346(5) . ?
C23 C24 1.388(6) . ?
C23 C28 1.389(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.376(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.359(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(6) . ?
C28 H28 0.9300 . ?
N1 N2 1.380(4) . ?
N2 Bi1 2.411(3) 2_666 ?
N4 N5 1.378(4) . ?
N5 Bi1 2.473(3) 2_666 ?
C29 H29 0.9601 . ?
C29 C31 1.381(9) . ?
C29 C31 1.82(3) 2_767 ?
C29 C30 1.406(9) . ?
C29 C33 0.54(2) 2_767 ?
C29 C34 0.937(18) 2_767 ?
C32 H32A 0.9599 . ?
C32 H32B 0.9601 . ?
C32 H32C 0.9600 . ?
C32 C31 1.512(10) . ?
C32 C30 1.96(2) 2_767 ?
C32 C34 1.57(2) 2_767 ?
C32 C35 0.69(2) 2_767 ?
C31 C29 1.82(3) 2_767 ?
C31 C31 1.77(3) 2_767 ?
C31 C30 1.54(3) 2_767 ?
C31 C33 1.52(3) 2_767 ?
C31 C33 1.375(9) . ?
C31 C34 0.99(3) 2_767 ?
C31 C35 0.94(2) 2_767 ?
C30 C32 1.96(2) 2_767 ?
C30 C31 1.54(3) 2_767 ?
C30 H30 0.9601 . ?
C30 C33 0.96(2) 2_767 ?
C30 C35 1.366(10) . ?
C33 C29 0.54(2) 2_767 ?
C33 C31 1.52(3) 2_767 ?
C33 C30 0.96(2) 2_767 ?
C33 H33 0.9600 . ?
C33 C34 1.389(9) . ?
C33 C35 1.79(2) 2_767 ?
C34 C29 0.937(18) 2_767 ?
C34 C32 1.57(2) 2_767 ?
C34 C31 0.99(3) 2_767 ?
C34 H34 0.9600 . ?
C34 C35 1.399(10) . ?
C35 C32 0.69(2) 2_767 ?
C35 C31 0.94(2) 2_767 ?
C35 C33 1.79(2) 2_767 ?
C35 H35 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
N1 Bi1 Bi1 71.47(7) . 2_666 ?
N1 Bi1 N5 88.41(11) . 2_666 ?
N2 Bi1 Bi1 72.85(7) 2_666 2_666 ?
N2 Bi1 N1 144.32(9) 2_666 . ?
N2 Bi1 N4 89.14(11) 2_666 . ?
N2 Bi1 N5 80.21(11) 2_666 2_666 ?
N4 Bi1 Bi1 72.65(7) . 2_666 ?
N4 Bi1 N1 80.72(11) . . ?
N4 Bi1 N5 144.45(9) . 2_666 ?
N5 Bi1 Bi1 71.80(7) 2_666 2_666 ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0(4) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 121.9(4) . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 C7 118.7(4) . . ?
N2 C7 C6 123.8(4) . . ?
N2 C7 N3 113.3(3) . . ?
N3 C7 C6 122.7(4) . . ?
N1 C8 C9 123.8(4) . . ?
N1 C8 N3 113.4(3) . . ?
N3 C8 C9 122.7(4) . . ?
C10 C9 C8 121.6(4) . . ?
C14 C9 C8 119.1(4) . . ?
C14 C9 C10 119.3(4) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(4) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(5) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(5) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(5) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 119.8(4) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 H15 119.6 . . ?
C16 C15 C20 120.8(4) . . ?
C20 C15 H15 119.6 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.7(4) . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 119.2(4) . . ?
C15 C20 C21 121.0(4) . . ?
C19 C20 C21 119.7(4) . . ?
N4 C21 C20 124.0(3) . . ?
N4 C21 N6 112.7(3) . . ?
N6 C21 C20 123.3(4) . . ?
N5 C22 C23 125.0(4) . . ?
N5 C22 N6 112.5(3) . . ?
N6 C22 C23 122.5(4) . . ?
C24 C23 C22 119.7(4) . . ?
C24 C23 C28 118.9(4) . . ?
C28 C23 C22 121.3(4) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.1(4) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(4) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.7(4) . . ?
C28 C27 H27 120.1 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.2(4) . . ?
C27 C28 H28 119.9 . . ?
C8 N1 Bi1 137.3(3) . . ?
C8 N1 N2 105.4(3) . . ?
N2 N1 Bi1 107.3(2) . . ?
C7 N2 Bi1 136.6(3) . 2_666 ?
C7 N2 N1 105.8(3) . . ?
N1 N2 Bi1 108.4(2) . 2_666 ?
C8 N3 C7 102.0(3) . . ?
C21 N4 Bi1 145.4(2) . . ?
C21 N4 N5 105.6(3) . . ?
N5 N4 Bi1 108.9(2) . . ?
C22 N5 Bi1 147.2(3) . 2_666 ?
C22 N5 N4 106.1(3) . . ?
N4 N5 Bi1 106.6(2) . 2_666 ?
C21 N6 C22 103.1(3) . . ?
C31 C29 H29 120.7 . . ?
C31 C29 H29 173.7 2_767 . ?
C31 C29 C31 65.5(13) . 2_767 ?
C31 C29 C30 120.6(15) . . ?
C30 C29 H29 118.7 . . ?
C30 C29 C31 55.1(9) . 2_767 ?
C33 C29 H29 144.7 2_767 . ?
C33 C29 C31 29(3) 2_767 2_767 ?
C33 C29 C31 94(4) 2_767 . ?
C33 C29 C30 27(3) 2_767 . ?
C33 C29 C34 139(5) 2_767 2_767 ?
C34 C29 H29 74.8 2_767 . ?
C34 C29 C31 111(2) 2_767 2_767 ?
C34 C29 C31 46.0(17) 2_767 . ?
C34 C29 C30 166(3) 2_767 . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C32 H32A 108.6 . . ?
C31 C32 H32B 109.8 . . ?
C31 C32 H32C 110.0 . . ?
C31 C32 C30 50.5(7) . 2_767 ?
C31 C32 C34 37.6(10) . 2_767 ?
C30 C32 H32A 58.1 2_767 . ?
C30 C32 H32B 126.6 2_767 . ?
C30 C32 H32C 123.8 2_767 . ?
C34 C32 H32A 146.1 2_767 . ?
C34 C32 H32B 90.6 2_767 . ?
C34 C32 H32C 87.7 2_767 . ?
C34 C32 C30 88.0(10) 2_767 2_767 ?
C35 C32 H32A 82.9 2_767 . ?
C35 C32 H32B 124.0 2_767 . ?
C35 C32 H32C 117.2 2_767 . ?
C35 C32 C31 26(2) 2_767 . ?
C35 C32 C30 24.9(19) 2_767 2_767 ?
C35 C32 C34 63.2(17) 2_767 2_767 ?
C29 C31 C29 114.5(13) . 2_767 ?
C29 C31 C32 116.8(9) . . ?
C29 C31 C31 69.3(14) . 2_767 ?
C29 C31 C30 163.1(12) . 2_767 ?
C29 C31 C33 20.6(12) . 2_767 ?
C32 C31 C29 128.7(10) . 2_767 ?
C32 C31 C31 173.7(13) . 2_767 ?
C32 C31 C30 80.1(8) . 2_767 ?
C32 C31 C33 137.3(13) . 2_767 ?
C31 C31 C29 45.2(6) 2_767 2_767 ?
C30 C31 C29 48.6(9) 2_767 2_767 ?
C30 C31 C31 93.8(14) 2_767 2_767 ?
C33 C31 C29 93.9(11) 2_767 2_767 ?
C33 C31 C29 10.9(9) . 2_767 ?
C33 C31 C29 125.3(14) . . ?
C33 C31 C32 117.9(9) . . ?
C33 C31 C31 48.7(7) 2_767 2_767 ?
C33 C31 C31 56.1(13) . 2_767 ?
C33 C31 C30 142.4(16) 2_767 2_767 ?
C33 C31 C30 37.9(8) . 2_767 ?
C33 C31 C33 104.8(15) . 2_767 ?
C34 C31 C29 156.7(17) 2_767 2_767 ?
C34 C31 C29 42.7(10) 2_767 . ?
C34 C31 C32 74.2(11) 2_767 . ?
C34 C31 C31 111.8(18) 2_767 2_767 ?
C34 C31 C30 153.8(16) 2_767 2_767 ?
C34 C31 C33 167.6(15) 2_767 . ?
C34 C31 C33 63.1(15) 2_767 2_767 ?
C35 C31 C29 135.3(19) 2_767 . ?
C35 C31 C29 110(2) 2_767 2_767 ?
C35 C31 C32 18.8(16) 2_767 . ?
C35 C31 C31 155(3) 2_767 2_767 ?
C35 C31 C30 61.4(15) 2_767 2_767 ?
C35 C31 C33 156(3) 2_767 2_767 ?
C35 C31 C33 99.3(18) 2_767 . ?
C35 C31 C34 92.6(18) 2_767 2_767 ?
C29 C30 C32 125.6(13) . 2_767 ?
C29 C30 C31 76.2(12) . 2_767 ?
C29 C30 H30 121.3 . . ?
C32 C30 H30 113.0 2_767 . ?
C31 C30 C32 49.4(8) 2_767 2_767 ?
C31 C30 H30 162.3 2_767 . ?
C33 C30 C29 14.6(18) 2_767 . ?
C33 C30 C32 111(2) 2_767 2_767 ?
C33 C30 C31 61.8(15) 2_767 2_767 ?
C33 C30 H30 135.6 2_767 . ?
C33 C30 C35 99(2) 2_767 . ?
C35 C30 C29 113.4(17) . . ?
C35 C30 C32 12.3(10) . 2_767 ?
C35 C30 C31 37.2(11) . 2_767 ?
C35 C30 H30 125.3 . . ?
C29 C33 C31 65(3) 2_767 2_767 ?
C29 C33 C31 140(4) 2_767 . ?
C29 C33 C30 139(5) 2_767 2_767 ?
C29 C33 H33 95.0 2_767 . ?
C29 C33 C34 26(3) 2_767 . ?
C29 C33 C35 169(4) 2_767 2_767 ?
C31 C33 C31 75.2(15) . 2_767 ?
C31 C33 H33 160.1 2_767 . ?
C31 C33 H33 124.6 . . ?
C31 C33 C34 114.8(17) . . ?
C31 C33 C35 31.3(9) . 2_767 ?
C31 C33 C35 106.4(18) 2_767 2_767 ?
C30 C33 C31 155(3) 2_767 2_767 ?
C30 C33 C31 80.3(17) 2_767 . ?
C30 C33 H33 44.4 2_767 . ?
C30 C33 C34 165(2) 2_767 . ?
C30 C33 C35 49.0(12) 2_767 2_767 ?
C34 C33 C31 39.7(11) . 2_767 ?
C34 C33 H33 120.5 . . ?
C34 C33 C35 146.1(16) . 2_767 ?
C35 C33 H33 93.4 2_767 . ?
C29 C34 C32 159(3) 2_767 2_767 ?
C29 C34 C31 91(2) 2_767 2_767 ?
C29 C34 C33 14.6(19) 2_767 . ?
C29 C34 H34 105.3 2_767 . ?
C29 C34 C35 133(3) 2_767 . ?
C32 C34 H34 95.0 2_767 . ?
C31 C34 C32 68.2(13) 2_767 2_767 ?
C31 C34 C33 77.2(16) 2_767 . ?
C31 C34 H34 163.1 2_767 . ?
C31 C34 C35 42.2(13) 2_767 . ?
C33 C34 C32 145.4(17) . 2_767 ?
C33 C34 H34 119.6 . . ?
C33 C34 C35 119.3(19) . . ?
C35 C34 C32 26.2(10) . 2_767 ?
C35 C34 H34 121.1 . . ?
C32 C35 C31 135(4) 2_767 2_767 ?
C32 C35 C30 143(3) 2_767 . ?
C32 C35 C33 173(3) 2_767 2_767 ?
C32 C35 C34 91(2) 2_767 . ?
C32 C35 H35 27.4 2_767 . ?
C31 C35 C30 81(2) 2_767 . ?
C31 C35 C33 49.4(12) 2_767 2_767 ?
C31 C35 C34 45.2(17) 2_767 . ?
C31 C35 H35 162.6 2_767 . ?
C30 C35 C33 32.0(11) . 2_767 ?
C30 C35 C34 126.5(19) . . ?
C30 C35 H35 115.6 . . ?
C33 C35 H35 147.5 2_767 . ?
C34 C35 C33 94.6(14) . 2_767 ?
C34 C35 H35 117.8 . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 58.989
_oxdiff_exptl_absorpt_empirical_full_min 0.451

####################################################################### 
# 
# 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_20190415-1
_database_code_depnum_ccdc_archive 'CCDC 1937538'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2019-06-30
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C32 H56 Bi2 N12'
_chemical_formula_sum            'C32 H56 Bi2 N12'
_chemical_formula_weight         1026.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.1097(3)
_cell_length_b                   10.1538(3)
_cell_length_c                   10.1748(4)
_cell_angle_alpha                97.933(3)
_cell_angle_beta                 99.017(3)
_cell_angle_gamma                96.358(3)
_cell_volume                     1012.28(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4715
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7520
_cell_measurement_theta_min      3.3680
_exptl_absorpt_coefficient_mu    8.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11744
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.09
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0251
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.8603
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  83.00   1.00   13.88    --   15.68  57.00-180.00   84
  2  ω    -54.00  35.00   1.00   13.88    --   15.68 -37.00   0.00   89
  3  ω    -11.00  83.00   1.00   13.88    --   15.68  77.00 -90.00   94
  4  ω     -1.00  83.00   1.00   13.88    --   15.68  57.00 150.00   84
  5  ω    -44.00  50.00   1.00   13.88    --  -17.25  77.00   0.00   94
  6  ω    -25.00  22.00   1.00   13.88    --  -17.25 -99.00 150.00   47
  7  ω    -52.00  34.00   1.00   13.88    --   15.68 -77.00-180.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0374916000
_diffrn_orient_matrix_UB_12      0.0550136000
_diffrn_orient_matrix_UB_13      0.0045669000
_diffrn_orient_matrix_UB_21      0.0611113000
_diffrn_orient_matrix_UB_22      0.0450183000
_diffrn_orient_matrix_UB_23      0.0180855000
_diffrn_orient_matrix_UB_31      0.0005564000
_diffrn_orient_matrix_UB_32      0.0037674000
_diffrn_orient_matrix_UB_33      -0.0690084000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3185
_reflns_number_total             3835
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         1.546
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0305P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C11, C11'}
{C14, C14'}
{C15, C15'}
3. Uiso/Uaniso restraints and constraints
C6 \\sim C7 \\sim C8: within 1.7A with sigma of 0.002 and sigma for terminal atoms of 0.002
C10 \\sim C11 \\sim C11' \\sim C10': within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C9) \\sim Ueq, Uanis(C9') \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C16') \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C11) = Uanis(C11')
Uanis(C14) = Uanis(C14')
Uanis(C15) = Uanis(C15')
4. Others
 Sof(C9')=Sof(H9'A)=Sof(H9'B)=Sof(H9'C)=Sof(C10')=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C11')=Sof(H11')=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=
 Sof(C11)=Sof(H11)=FVAR(1)
 Sof(C14')=Sof(H14')=Sof(C15')=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16')=
 Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(2)
 Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16)=Sof(H16A)=
 Sof(H16B)=Sof(H16C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C11(H11), C11'(H11'), C14(H14), C14'(H14'), C6(H6)
5.b Me refined with riding coordinates:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C9'(H9'A,H9'B,H9'C), C10'(H10D,H10E,
 H10F), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C15'(H15D,H15E,H15F),
 C16'(H16D,H16E,H16F), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.47881(2) 1.13270(2) 1.05302(2) 0.05388(12) Uani 1 1 d . . .
C1 C 0.3139(13) 1.0647(11) 1.5267(9) 0.151(5) Uani 1 1 d . . .
H1A H 0.4103 1.0776 1.5536 0.227 Uiso 1 1 calc R . .
H1B H 0.2774 0.9787 1.5442 0.227 Uiso 1 1 calc R . .
H1C H 0.2763 1.1340 1.5770 0.227 Uiso 1 1 calc R . .
C2 C 0.2807(11) 1.0703(8) 1.3874(8) 0.099(3) Uani 1 1 d . . .
H2 H 0.1822 1.0472 1.3680 0.119 Uiso 1 1 calc R . .
C3 C 0.3021(12) 1.2006(8) 1.3475(10) 0.127(4) Uani 1 1 d . . .
H3A H 0.2585 1.2627 1.4003 0.190 Uiso 1 1 calc R . .
H3B H 0.2647 1.1947 1.2538 0.190 Uiso 1 1 calc R . .
H3C H 0.3972 1.2314 1.3618 0.190 Uiso 1 1 calc R . .
C4 C 0.3296(8) 0.9599(7) 1.2970(7) 0.070(2) Uani 1 1 d . . .
C5 C 0.3661(8) 0.7684(7) 1.2173(7) 0.072(2) Uani 1 1 d . . .
C12 C 0.1787(8) 0.8598(8) 0.7547(8) 0.076(2) Uani 1 1 d . . .
C13 C 0.1588(8) 1.0571(8) 0.8370(8) 0.074(2) Uani 1 1 d . . .
N1 N 0.3908(6) 0.9769(5) 1.1953(5) 0.0584(14) Uani 1 1 d . . .
N2 N 0.4139(6) 0.8502(5) 1.1413(5) 0.0617(15) Uani 1 1 d . . .
N3 N 0.3138(8) 0.8294(6) 1.3170(7) 0.085(2) Uani 1 1 d . . .
N4 N 0.2801(6) 1.0356(5) 0.8922(5) 0.0578(14) Uani 1 1 d . A .
N5 N 0.2944(6) 0.9066(5) 0.8381(5) 0.0603(14) Uani 1 1 d . . .
N6 N 0.0915(7) 0.9495(8) 0.7516(8) 0.091(2) Uani 1 1 d . A .
C9 C 0.224(3) 0.636(3) 0.726(3) 0.178(13) Uani 0.486(13) 1 d PU A 1
H9A H 0.2180 0.5576 0.6601 0.268 Uiso 0.486(13) 1 calc PR A 1
H9B H 0.1906 0.6112 0.8040 0.268 Uiso 0.486(13) 1 calc PR A 1
H9C H 0.3164 0.6767 0.7521 0.268 Uiso 0.486(13) 1 calc PR A 1
C10 C 0.056(2) 0.716(2) 0.553(3) 0.150(3) Uani 0.486(13) 1 d PU A 1
H10A H 0.0920 0.6765 0.4778 0.225 Uiso 0.486(13) 1 calc PR A 1
H10B H 0.0390 0.8058 0.5412 0.225 Uiso 0.486(13) 1 calc PR A 1
H10C H -0.0275 0.6636 0.5584 0.225 Uiso 0.486(13) 1 calc PR A 1
C11 C 0.1508(13) 0.7219(12) 0.6752(14) 0.148(2) Uani 0.486(13) 1 d PU A 1
H11 H 0.0781 0.6968 0.7240 0.178 Uiso 0.486(13) 1 calc PR A 1
C9' C 0.2669(19) 0.6618(18) 0.645(2) 0.099(6) Uani 0.514(13) 1 d PU A 2
H9'A H 0.3101 0.6310 0.7242 0.149 Uiso 0.514(13) 1 calc PR A 2
H9'B H 0.3292 0.7270 0.6185 0.149 Uiso 0.514(13) 1 calc PR A 2
H9'C H 0.2389 0.5873 0.5736 0.149 Uiso 0.514(13) 1 calc PR A 2
C10' C 0.038(2) 0.640(2) 0.693(3) 0.150(3) Uani 0.514(13) 1 d PU A 2
H10D H 0.0615 0.5959 0.7694 0.225 Uiso 0.514(13) 1 calc PR A 2
H10E H 0.0081 0.5732 0.6138 0.225 Uiso 0.514(13) 1 calc PR A 2
H10F H -0.0325 0.6925 0.7073 0.225 Uiso 0.514(13) 1 calc PR A 2
C11' C 0.1508(13) 0.7219(12) 0.6752(14) 0.148(2) Uani 0.514(13) 1 d PU A 2
H11' H 0.1170 0.7437 0.5863 0.178 Uiso 0.514(13) 1 calc PR A 2
C14 C 0.1034(10) 1.1852(11) 0.8720(12) 0.114(4) Uani 0.56(2) 1 d P A 3
H14 H 0.1791 1.2453 0.9296 0.137 Uiso 0.56(2) 1 calc PR A 3
C15 C 0.0014(13) 1.1771(12) 0.9513(12) 0.152(5) Uani 0.56(2) 1 d P A 3
H15A H -0.0727 1.1112 0.9049 0.229 Uiso 0.56(2) 1 calc PR A 3
H15B H -0.0297 1.2629 0.9672 0.229 Uiso 0.56(2) 1 calc PR A 3
H15C H 0.0370 1.1516 1.0358 0.229 Uiso 0.56(2) 1 calc PR A 3
C16 C 0.069(2) 1.2533(18) 0.746(2) 0.109(8) Uani 0.56(2) 1 d PU A 3
H16A H 0.0096 1.1911 0.6769 0.164 Uiso 0.56(2) 1 calc PR A 3
H16B H 0.1510 1.2805 0.7147 0.164 Uiso 0.56(2) 1 calc PR A 3
H16C H 0.0259 1.3306 0.7699 0.164 Uiso 0.56(2) 1 calc PR A 3
C14' C 0.1034(10) 1.1852(11) 0.8720(12) 0.114(4) Uani 0.44(2) 1 d P A 4
H14' H 0.0401 1.1746 0.7866 0.137 Uiso 0.44(2) 1 calc PR A 4
C15' C 0.0014(13) 1.1771(12) 0.9513(12) 0.152(5) Uani 0.44(2) 1 d P A 4
H15D H 0.0248 1.2455 1.0293 0.229 Uiso 0.44(2) 1 calc PR A 4
H15E H -0.0074 1.0905 0.9792 0.229 Uiso 0.44(2) 1 calc PR A 4
H15F H -0.0828 1.1897 0.8994 0.229 Uiso 0.44(2) 1 calc PR A 4
C16' C 0.169(3) 1.291(3) 0.854(3) 0.143(13) Uani 0.44(2) 1 d PU A 4
H16D H 0.2456 1.3168 0.9248 0.214 Uiso 0.44(2) 1 calc PR A 4
H16E H 0.1124 1.3604 0.8531 0.214 Uiso 0.44(2) 1 calc PR A 4
H16F H 0.1995 1.2754 0.7687 0.214 Uiso 0.44(2) 1 calc PR A 4
C6 C 0.3741(15) 0.6206(11) 1.1921(18) 0.185(4) Uani 1 1 d U . .
H6 H 0.4052 0.6011 1.1058 0.223 Uiso 1 1 calc R . .
C7 C 0.2475(14) 0.5451(10) 1.1794(15) 0.188(4) Uani 1 1 d U . .
H7A H 0.2360 0.4731 1.1051 0.282 Uiso 1 1 calc R . .
H7B H 0.1783 0.6015 1.1636 0.282 Uiso 1 1 calc R . .
H7C H 0.2411 0.5089 1.2608 0.282 Uiso 1 1 calc R . .
C8 C 0.4659(13) 0.5782(10) 1.2897(16) 0.189(4) Uani 1 1 d U . .
H8A H 0.4533 0.6166 1.3777 0.283 Uiso 1 1 calc R . .
H8B H 0.5564 0.6067 1.2779 0.283 Uiso 1 1 calc R . .
H8C H 0.4511 0.4821 1.2805 0.283 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Bi1 2.8650(4) 2_677 ?
Bi1 N1 2.472(5) . ?
Bi1 N2 2.417(5) 2_677 ?
Bi1 N4 2.402(5) . ?
Bi1 N5 2.484(6) 2_677 ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.416(12) . ?
C2 H2 0.9800 . ?
C2 C3 1.441(11) . ?
C2 C4 1.526(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N1 1.308(8) . ?
C4 N3 1.363(9) . ?
C5 N2 1.313(8) . ?
C5 N3 1.327(8) . ?
C5 C6 1.501(12) . ?
C12 N5 1.330(9) . ?
C12 N6 1.336(9) . ?
C12 C11 1.491(12) . ?
C13 N4 1.321(8) . ?
C13 N6 1.341(10) . ?
C13 C14 1.493(11) . ?
N1 N2 1.387(6) . ?
N2 Bi1 2.417(5) 2_677 ?
N4 N5 1.381(6) . ?
N5 Bi1 2.484(6) 2_677 ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C11 1.31(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 C11 1.44(2) . ?
C11 H11 0.9800 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.407(13) . ?
C14 C16 1.54(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C6 H6 0.9800 . ?
C6 C7 1.395(16) . ?
C6 C8 1.397(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
N1 Bi1 Bi1 72.04(11) . 2_677 ?
N1 Bi1 N5 85.22(18) . 2_677 ?
N2 Bi1 Bi1 72.77(12) 2_677 2_677 ?
N2 Bi1 N1 144.81(15) 2_677 . ?
N2 Bi1 N5 84.11(18) 2_677 2_677 ?
N4 Bi1 Bi1 72.89(11) . 2_677 ?
N4 Bi1 N1 84.23(18) . . ?
N4 Bi1 N2 85.37(19) . 2_677 ?
N4 Bi1 N5 144.62(16) . 2_677 ?
N5 Bi1 Bi1 71.73(12) 2_677 2_677 ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2 103.4 . . ?
C1 C2 C3 116.7(9) . . ?
C1 C2 C4 114.0(8) . . ?
C3 C2 H2 103.4 . . ?
C3 C2 C4 113.7(7) . . ?
C4 C2 H2 103.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C2 125.6(7) . . ?
N1 C4 N3 112.6(6) . . ?
N3 C4 C2 121.8(7) . . ?
N2 C5 N3 113.7(6) . . ?
N2 C5 C6 121.8(9) . . ?
N3 C5 C6 124.5(9) . . ?
N5 C12 N6 112.5(7) . . ?
N5 C12 C11 123.1(8) . . ?
N6 C12 C11 124.4(9) . . ?
N4 C13 N6 112.1(7) . . ?
N4 C13 C14 122.9(8) . . ?
N6 C13 C14 125.0(8) . . ?
C4 N1 Bi1 148.0(4) . . ?
C4 N1 N2 105.8(5) . . ?
N2 N1 Bi1 106.2(3) . . ?
C5 N2 Bi1 145.4(4) . 2_677 ?
C5 N2 N1 105.6(5) . . ?
N1 N2 Bi1 109.0(4) . 2_677 ?
C5 N3 C4 102.3(6) . . ?
C13 N4 Bi1 143.9(5) . . ?
C13 N4 N5 106.3(6) . . ?
N5 N4 Bi1 109.7(4) . . ?
C12 N5 Bi1 148.9(4) . 2_677 ?
C12 N5 N4 105.4(5) . . ?
N4 N5 Bi1 105.7(4) . 2_677 ?
C12 N6 C13 103.7(7) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C9 H9A 109.5 . . ?
C11 C9 H9B 109.5 . . ?
C11 C9 H9C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
C12 C11 H11 91.5 . . ?
C9 C11 C12 114.1(17) . . ?
C9 C11 C10 134.4(19) . . ?
C9 C11 H11 91.5 . . ?
C10 C11 C12 111.3(13) . . ?
C10 C11 H11 91.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
H10D C10' H10E 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C13 C14 H14 104.9 . . ?
C13 C14 C16 111.2(10) . . ?
C15 C14 C13 115.0(9) . . ?
C15 C14 H14 104.9 . . ?
C15 C14 C16 114.7(10) . . ?
C16 C14 H14 104.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16D C16' H16E 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C5 C6 H6 107.3 . . ?
C7 C6 C5 111.6(11) . . ?
C7 C6 H6 107.3 . . ?
C7 C6 C8 109.6(13) . . ?
C8 C6 C5 113.6(11) . . ?
C8 C6 H6 107.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.633
_oxdiff_exptl_absorpt_empirical_full_min 0.674

