# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2003413'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT201_1                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          8 Report
RESPONSE: Disordering of the butyl groups
;
# Added during the CSD deposition process: Tuesday 12 May 2020 07:00 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H52 Bi2 Cl10 N4'
_chemical_formula_weight         1313.27

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

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

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

_cell_length_a                   10.4247(3)
_cell_length_b                   14.2467(8)
_cell_length_c                   15.6532(6)
_cell_angle_alpha                85.418(4)
_cell_angle_beta                 85.632(3)
_cell_angle_gamma                89.424(3)
_cell_volume                     2310.60(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4727
_cell_measurement_theta_min      3.5920
_cell_measurement_theta_max      28.5360

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    8.215
_shelx_estimated_absorpt_T_min   0.439
_shelx_estimated_absorpt_T_max   0.559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83752
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            17102
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.371
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8756
_reflns_number_gt                6039
_reflns_threshold_expression     >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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0158P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8756
_refine_ls_number_parameters     445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0714
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3548(8) 0.5338(6) 0.4251(5) 0.045(2) Uani 1 1 d . . . . .
H1A H 0.405475 0.554525 0.470368 0.068 Uiso 1 1 calc R U . . .
H1B H 0.272827 0.568081 0.425604 0.068 Uiso 1 1 calc R U . . .
H1C H 0.338327 0.466105 0.435473 0.068 Uiso 1 1 calc R U . . .
C2 C 0.4290(7) 0.5535(6) 0.3384(5) 0.038(2) Uani 1 1 d . . . . .
H2A H 0.512504 0.519927 0.339042 0.045 Uiso 1 1 calc R U . . .
H2B H 0.447059 0.621816 0.329181 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3578(6) 0.5236(5) 0.2635(4) 0.0261(17) Uani 1 1 d . . . . .
H3A H 0.273302 0.556041 0.263950 0.031 Uiso 1 1 calc R U . . .
H3B H 0.407448 0.544930 0.209073 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3360(6) 0.4188(5) 0.2647(5) 0.0263(18) Uani 1 1 d . . . . .
H4A H 0.281663 0.397212 0.317158 0.032 Uiso 1 1 calc R U . . .
H4B H 0.289801 0.405091 0.214192 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4953(6) 0.3145(5) 0.3331(4) 0.0248(17) Uani 1 1 d . . . . .
H5A H 0.437575 0.309433 0.383182 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6114(6) 0.2687(5) 0.3338(4) 0.0227(16) Uani 1 1 d . . . . .
H6A H 0.634203 0.231870 0.383747 0.027 Uiso 1 1 calc R U . . .
C7 C 0.5434(6) 0.3746(5) 0.1902(4) 0.0228(17) Uani 1 1 d . . . . .
H7A H 0.519311 0.411760 0.140860 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6594(6) 0.3294(5) 0.1887(4) 0.0187(16) Uani 1 1 d . . . . .
H8A H 0.715511 0.334295 0.137809 0.022 Uiso 1 1 calc R U . . .
C9 C 0.6953(6) 0.2769(5) 0.2603(4) 0.0204(16) Uani 1 1 d . . . . .
C10 C 0.8217(6) 0.2269(5) 0.2595(4) 0.0177(15) Uani 1 1 d . . . . .
C11 C 0.9196(6) 0.2511(5) 0.1952(4) 0.0244(17) Uani 1 1 d . . . . .
H11A H 0.903011 0.296678 0.149679 0.029 Uiso 1 1 calc R U . . .
C12 C 1.0378(6) 0.2101(5) 0.1973(4) 0.0248(17) Uani 1 1 d . . . . .
H12A H 1.103075 0.228088 0.153508 0.030 Uiso 1 1 calc R U . . .
C13 C 0.8524(6) 0.1576(5) 0.3234(4) 0.0213(17) Uani 1 1 d . . . . .
H13A H 0.788999 0.137316 0.367600 0.026 Uiso 1 1 calc R U . . .
C14 C 0.9744(6) 0.1185(5) 0.3225(4) 0.0196(16) Uani 1 1 d . . . . .
H14A H 0.994442 0.072485 0.366870 0.024 Uiso 1 1 calc R U . . .
C15 C 1.1934(6) 0.1003(5) 0.2582(4) 0.0235(17) Uani 1 1 d . . . . .
H15A H 1.197704 0.054190 0.308714 0.028 Uiso 1 1 calc R U . . .
H15B H 1.258480 0.149493 0.262410 0.028 Uiso 1 1 calc R U . . .
C16 C 1.2256(7) 0.0508(5) 0.1771(5) 0.0321(18) Uani 1 1 d . . . . .
H16A H 1.315295 0.027298 0.177396 0.039 Uiso 1 1 calc R U . . .
H16B H 1.221308 0.097314 0.126871 0.039 Uiso 1 1 calc R U . . .
C17 C 1.1366(7) -0.0323(6) 0.1658(5) 0.042(2) Uani 1 1 d . . . . .
H17A H 1.184988 -0.076829 0.129854 0.051 Uiso 1 1 calc R U . . .
H17B H 1.115729 -0.065795 0.222976 0.051 Uiso 1 1 calc R U . . .
C18 C 1.0139(7) -0.0084(6) 0.1265(5) 0.045(2) Uani 1 1 d . . . . .
H18A H 0.965181 -0.066084 0.122415 0.067 Uiso 1 1 calc R U . . .
H18B H 0.963085 0.033959 0.162295 0.067 Uiso 1 1 calc R U . . .
H18C H 1.032565 0.022890 0.068876 0.067 Uiso 1 1 calc R U . . .
C23 C 1.0140(6) 0.3172(5) 0.7572(4) 0.0217(16) Uani 1 1 d . . . . .
H23A H 1.070623 0.343294 0.793714 0.026 Uiso 1 1 calc R U . . .
C24 C 0.8936(5) 0.2893(5) 0.7900(4) 0.0197(15) Uani 1 1 d . . . . .
H24A H 0.867770 0.295412 0.848783 0.024 Uiso 1 1 calc R U . . .
C25 C 0.9742(6) 0.2702(5) 0.6235(5) 0.0252(17) Uani 1 1 d . . . . .
H25A H 1.004406 0.261765 0.565807 0.030 Uiso 1 1 calc R U . . .
C26 C 0.8528(6) 0.2432(5) 0.6509(4) 0.0182(15) Uani 1 1 d . . . . .
H26A H 0.797971 0.218667 0.612392 0.022 Uiso 1 1 calc R U . . .
C27 C 0.8090(6) 0.2520(5) 0.7370(4) 0.0207(16) Uani 1 1 d . . . . .
C28 C 0.6783(6) 0.2213(5) 0.7710(4) 0.0163(15) Uani 1 1 d . . . . .
C29 C 0.6221(6) 0.2537(5) 0.8461(4) 0.0254(18) Uani 1 1 d . . . . .
H29A H 0.668612 0.295748 0.876258 0.031 Uiso 1 1 calc R U . . .
C30 C 0.5009(6) 0.2266(5) 0.8780(4) 0.0214(16) Uani 1 1 d . . . . .
H30A H 0.463498 0.249544 0.929618 0.026 Uiso 1 1 calc R U . . .
C31 C 0.6078(5) 0.1582(5) 0.7291(4) 0.0195(15) Uani 1 1 d . . . . .
H31A H 0.643767 0.132936 0.678232 0.023 Uiso 1 1 calc R U . . .
C32 C 0.4865(6) 0.1332(5) 0.7623(4) 0.0219(16) Uani 1 1 d . . . . .
H32A H 0.437699 0.091567 0.733190 0.026 Uiso 1 1 calc R U . . .
N1 N 1.0536(5) 0.3086(4) 0.6749(3) 0.0206(13) Uani 1 1 d . . . . .
N2 N 0.4356(4) 0.1665(4) 0.8347(3) 0.0209(13) Uani 1 1 d . . . . .
N3 N 0.4616(5) 0.3662(4) 0.2633(4) 0.0212(13) Uani 1 1 d . . . . .
N4 N 1.0636(5) 0.1444(4) 0.2605(3) 0.0216(13) Uani 1 1 d . . . . .
Cl1 Cl 0.48020(15) 0.23366(12) 0.55020(10) 0.0245(4) Uani 1 1 d . . . . .
Cl2 Cl 0.31057(15) 0.39860(13) 0.84345(10) 0.0230(4) Uani 1 1 d . . . . .
Cl3 Cl 0.00565(17) 0.52208(14) 0.87786(11) 0.0308(4) Uani 1 1 d . . . . .
Cl4 Cl 0.18628(15) -0.04720(13) 0.46659(10) 0.0248(4) Uani 1 1 d . . . . .
Cl5 Cl 0.51746(15) 0.04249(12) 0.37977(10) 0.0207(4) Uani 1 1 d . . . . .
Cl6 Cl 0.32008(17) 0.56064(14) 1.02190(11) 0.0322(5) Uani 1 1 d . . . . .
Cl7 Cl 0.03378(15) 0.26119(13) 0.97599(11) 0.0262(4) Uani 1 1 d . . . . .
Cl8 Cl 0.32316(15) 0.29800(12) 1.07218(10) 0.0226(4) Uani 1 1 d . . . . .
Cl9 Cl 0.19671(15) 0.21856(13) 0.43637(10) 0.0228(4) Uani 1 1 d . . . . .
Cl10 Cl 0.18622(15) 0.09712(12) 0.65977(10) 0.0221(4) Uani 1 1 d . . . . .
Bi1 Bi 0.33223(2) 0.08803(2) 0.51851(2) 0.01611(8) Uani 1 1 d . . . . .
Bi2 Bi 0.17489(2) 0.41883(2) 0.98679(2) 0.01925(8) Uani 1 1 d . . . . .
C19A C 1.0853(7) 0.6088(6) 0.5991(5) 0.045(2) Uiso 0.3 1 d . . P A 1
H19A H 1.040361 0.649704 0.639123 0.067 Uiso 0.3 1 calc R U P A 1
H19B H 1.168404 0.636765 0.577953 0.067 Uiso 0.3 1 calc R U P A 1
H19C H 1.033090 0.601948 0.550496 0.067 Uiso 0.3 1 calc R U P A 1
C20A C 1.107(2) 0.5148(16) 0.6440(15) 0.020(5) Uiso 0.3 1 d . . P A 1
H20A H 1.021723 0.489497 0.666816 0.025 Uiso 0.3 1 calc R U P A 1
H20D H 1.156370 0.524142 0.694138 0.025 Uiso 0.3 1 calc R U P A 1
C21A C 1.177(2) 0.4373(18) 0.5924(17) 0.029(6) Uiso 0.3 1 d . . P A 1
H21A H 1.132871 0.430121 0.539673 0.035 Uiso 0.3 1 calc R U P A 1
H21B H 1.266394 0.458300 0.574530 0.035 Uiso 0.3 1 calc R U P A 1
C22A C 1.1822(6) 0.3453(5) 0.6419(4) 0.0246(16) Uiso 0.3 1 d . . P A 1
H22A H 1.235243 0.351046 0.691056 0.029 Uiso 0.3 1 calc R U P A 1
H22B H 1.225056 0.299326 0.604876 0.029 Uiso 0.3 1 calc R U P A 1
C19B C 1.0853(7) 0.6088(6) 0.5991(5) 0.045(2) Uiso 0.7 1 d . . P A 2
H19D H 1.016935 0.640332 0.567868 0.067 Uiso 0.7 1 calc R U P A 2
H19E H 1.075788 0.623432 0.659358 0.067 Uiso 0.7 1 calc R U P A 2
H19F H 1.169276 0.630852 0.573146 0.067 Uiso 0.7 1 calc R U P A 2
C20B C 1.0760(10) 0.5029(8) 0.5942(8) 0.036(3) Uiso 0.7 1 d . . P A 2
H20B H 0.990735 0.480677 0.619637 0.043 Uiso 0.7 1 calc R U P A 2
H20C H 1.084365 0.488108 0.533295 0.043 Uiso 0.7 1 calc R U P A 2
C21B C 1.1792(9) 0.4531(8) 0.6413(7) 0.027(2) Uiso 0.7 1 d . . P A 2
H21C H 1.170044 0.469849 0.701614 0.033 Uiso 0.7 1 calc R U P A 2
H21D H 1.263309 0.477422 0.615740 0.033 Uiso 0.7 1 calc R U P A 2
C22B C 1.1822(6) 0.3453(5) 0.6419(4) 0.0246(16) Uiso 0.7 1 d . . P A 2
H22C H 1.203645 0.326421 0.582971 0.029 Uiso 0.7 1 calc R U P A 2
H22D H 1.248681 0.319168 0.679115 0.029 Uiso 0.7 1 calc R U P A 2
C33A C 0.3050(6) 0.1370(5) 0.8701(4) 0.0232(16) Uiso 0.3 1 d . . P B 3
H33A H 0.254912 0.118830 0.822787 0.028 Uiso 0.3 1 calc R U P B 3
H33B H 0.260480 0.190766 0.895962 0.028 Uiso 0.3 1 calc R U P B 3
C34A C 0.3099(7) 0.0556(6) 0.9368(5) 0.045(2) Uiso 0.3 1 d . . P B 3
H34A H 0.312910 0.085064 0.991825 0.054 Uiso 0.3 1 calc R U P B 3
H34D H 0.224019 0.026191 0.938930 0.054 Uiso 0.3 1 calc R U P B 3
C35A C 0.3983(18) -0.0223(15) 0.9432(13) 0.014(5) Uiso 0.3 1 d . . P B 3
H35A H 0.399630 -0.051026 1.002811 0.017 Uiso 0.3 1 calc R U P B 3
H35B H 0.486697 -0.004207 0.920624 0.017 Uiso 0.3 1 calc R U P B 3
C36A C 0.335(3) -0.088(3) 0.884(2) 0.058(9) Uiso 0.3 1 d . . P B 3
H36A H 0.384555 -0.146168 0.881199 0.087 Uiso 0.3 1 calc R U P B 3
H36B H 0.246723 -0.102192 0.907632 0.087 Uiso 0.3 1 calc R U P B 3
H36C H 0.332788 -0.055911 0.826390 0.087 Uiso 0.3 1 calc R U P B 3
C33B C 0.3050(6) 0.1370(5) 0.8701(4) 0.0232(16) Uiso 0.7 1 d . . P B 4
H33C H 0.254912 0.118830 0.822787 0.028 Uiso 0.7 1 calc R U P B 4
H33D H 0.260480 0.190766 0.895962 0.028 Uiso 0.7 1 calc R U P B 4
C34B C 0.3099(7) 0.0556(6) 0.9368(5) 0.045(2) Uiso 0.7 1 d . . P B 4
H34B H 0.223826 0.045448 0.967240 0.054 Uiso 0.7 1 calc R U P B 4
H34C H 0.371051 0.069394 0.979548 0.054 Uiso 0.7 1 calc R U P B 4
C35B C 0.3553(12) -0.0372(9) 0.8907(8) 0.045(3) Uiso 0.7 1 d . . P B 4
H35C H 0.305077 -0.042469 0.840168 0.054 Uiso 0.7 1 calc R U P B 4
H35D H 0.447088 -0.030591 0.869808 0.054 Uiso 0.7 1 calc R U P B 4
C36B C 0.3393(11) -0.1248(10) 0.9481(9) 0.057(4) Uiso 0.7 1 d . . P B 4
H36D H 0.368438 -0.178797 0.916596 0.086 Uiso 0.7 1 calc R U P B 4
H36E H 0.390427 -0.120860 0.997699 0.086 Uiso 0.7 1 calc R U P B 4
H36F H 0.248324 -0.132746 0.968040 0.086 Uiso 0.7 1 calc R U P B 4


_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 1.518(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.525(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.512(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N3 1.501(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.335(8) . ?
C5 C6 1.371(9) . ?
C5 H5A 0.9500 . ?
C6 C9 1.389(9) . ?
C6 H6A 0.9500 . ?
C7 C8 1.364(9) . ?
C7 N3 1.371(8) . ?
C7 H7A 0.9500 . ?
C8 C9 1.371(9) . ?
C8 H8A 0.9500 . ?
C9 C10 1.491(8) . ?
C10 C13 1.400(9) . ?
C10 C11 1.403(9) . ?
C11 C12 1.360(9) . ?
C11 H11A 0.9500 . ?
C12 N4 1.347(8) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(9) . ?
C13 H13A 0.9500 . ?
C14 N4 1.325(8) . ?
C14 H14A 0.9500 . ?
C15 N4 1.486(8) . ?
C15 C16 1.515(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.542(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.486(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C23 N1 1.336(8) . ?
C23 C24 1.370(8) . ?
C23 H23A 0.9500 . ?
C24 C27 1.392(8) . ?
C24 H24A 0.9500 . ?
C25 N1 1.347(8) . ?
C25 C26 1.354(9) . ?
C25 H25A 0.9500 . ?
C26 C27 1.404(9) . ?
C26 H26A 0.9500 . ?
C27 C28 1.481(8) . ?
C28 C29 1.384(9) . ?
C28 C31 1.400(9) . ?
C29 C30 1.370(9) . ?
C29 H29A 0.9500 . ?
C30 N2 1.353(8) . ?
C30 H30A 0.9500 . ?
C31 C32 1.369(8) . ?
C31 H31A 0.9500 . ?
C32 N2 1.335(8) . ?
C32 H32A 0.9500 . ?
N1 C22B 1.485(8) . ?
N1 C22A 1.485(8) . ?
N2 C33B 1.482(8) . ?
N2 C33A 1.482(8) . ?
Cl1 Bi1 2.6972(16) . ?
Cl2 Bi2 2.5942(16) . ?
Cl3 Bi2 2.8617(18) . ?
Cl3 Bi2 2.8958(18) 2_567 ?
Cl4 Bi1 2.6805(16) . ?
Cl5 Bi1 2.8804(17) 2_656 ?
Cl5 Bi1 2.9030(16) . ?
Cl6 Bi2 2.6533(17) . ?
Cl7 Bi2 2.7206(17) . ?
Cl8 Bi2 2.6519(17) . ?
Cl9 Bi1 2.6361(17) . ?
Cl10 Bi1 2.5984(16) . ?
C19A C20A 1.49(2) . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20A C21A 1.57(3) . ?
C20A H20A 0.9900 . ?
C20A H20D 0.9900 . ?
C21A C22A 1.47(3) . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C19B C20B 1.521(14) . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20B C21B 1.492(14) . ?
C20B H20B 0.9900 . ?
C20B H20C 0.9900 . ?
C21B C22B 1.534(12) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C33A C34A 1.501(10) . ?
C33A H33A 0.9900 . ?
C33A H33B 0.9900 . ?
C34A C35A 1.44(2) . ?
C34A H34A 0.9900 . ?
C34A H34D 0.9900 . ?
C35A C36A 1.55(3) . ?
C35A H35A 0.9900 . ?
C35A H35B 0.9900 . ?
C36A H36A 0.9800 . ?
C36A H36B 0.9800 . ?
C36A H36C 0.9800 . ?
C33B C34B 1.501(10) . ?
C33B H33C 0.9900 . ?
C33B H33D 0.9900 . ?
C34B C35B 1.607(15) . ?
C34B H34B 0.9900 . ?
C34B H34C 0.9900 . ?
C35B C36B 1.481(18) . ?
C35B H35C 0.9900 . ?
C35B H35D 0.9900 . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 113.5(6) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 114.4(6) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N3 C4 C3 110.8(5) . . ?
N3 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N3 C5 C6 121.3(6) . . ?
N3 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C9 118.9(6) . . ?
C5 C6 H6A 120.6 . . ?
C9 C6 H6A 120.6 . . ?
C8 C7 N3 119.8(6) . . ?
C8 C7 H7A 120.1 . . ?
N3 C7 H7A 120.1 . . ?
C7 C8 C9 120.3(6) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C8 C9 C6 119.4(7) . . ?
C8 C9 C10 120.9(6) . . ?
C6 C9 C10 119.7(6) . . ?
C13 C10 C11 116.2(6) . . ?
C13 C10 C9 123.2(6) . . ?
C11 C10 C9 120.5(6) . . ?
C12 C11 C10 120.8(7) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
N4 C12 C11 120.9(6) . . ?
N4 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C14 C13 C10 120.5(6) . . ?
C14 C13 H13A 119.7 . . ?
C10 C13 H13A 119.7 . . ?
N4 C14 C13 120.7(6) . . ?
N4 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
N4 C15 C16 112.6(5) . . ?
N4 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N4 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 114.4(6) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 116.4(7) . . ?
C18 C17 H17A 108.2 . . ?
C16 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C16 C17 H17B 108.2 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C23 C24 121.4(6) . . ?
N1 C23 H23A 119.3 . . ?
C24 C23 H23A 119.3 . . ?
C23 C24 C27 120.0(6) . . ?
C23 C24 H24A 120.0 . . ?
C27 C24 H24A 120.0 . . ?
N1 C25 C26 122.5(6) . . ?
N1 C25 H25A 118.8 . . ?
C26 C25 H25A 118.8 . . ?
C25 C26 C27 119.1(6) . . ?
C25 C26 H26A 120.4 . . ?
C27 C26 H26A 120.4 . . ?
C24 C27 C26 117.6(6) . . ?
C24 C27 C28 120.9(6) . . ?
C26 C27 C28 121.4(6) . . ?
C29 C28 C31 117.6(6) . . ?
C29 C28 C27 120.9(6) . . ?
C31 C28 C27 121.5(6) . . ?
C30 C29 C28 121.6(6) . . ?
C30 C29 H29A 119.2 . . ?
C28 C29 H29A 119.2 . . ?
N2 C30 C29 118.7(6) . . ?
N2 C30 H30A 120.6 . . ?
C29 C30 H30A 120.6 . . ?
C32 C31 C28 119.4(6) . . ?
C32 C31 H31A 120.3 . . ?
C28 C31 H31A 120.3 . . ?
N2 C32 C31 121.1(6) . . ?
N2 C32 H32A 119.5 . . ?
C31 C32 H32A 119.5 . . ?
C23 N1 C25 119.3(6) . . ?
C23 N1 C22B 118.9(5) . . ?
C25 N1 C22B 121.7(5) . . ?
C23 N1 C22A 118.9(5) . . ?
C25 N1 C22A 121.7(5) . . ?
C32 N2 C30 121.6(5) . . ?
C32 N2 C33B 120.0(5) . . ?
C30 N2 C33B 118.4(5) . . ?
C32 N2 C33A 120.0(5) . . ?
C30 N2 C33A 118.4(5) . . ?
C5 N3 C7 120.3(6) . . ?
C5 N3 C4 120.5(5) . . ?
C7 N3 C4 119.1(6) . . ?
C14 N4 C12 120.7(6) . . ?
C14 N4 C15 120.7(6) . . ?
C12 N4 C15 118.6(5) . . ?
Bi2 Cl3 Bi2 96.91(5) . 2_567 ?
Bi1 Cl5 Bi1 96.47(5) 2_656 . ?
Cl10 Bi1 Cl9 92.14(5) . . ?
Cl10 Bi1 Cl4 91.76(5) . . ?
Cl9 Bi1 Cl4 90.61(5) . . ?
Cl10 Bi1 Cl1 93.59(5) . . ?
Cl9 Bi1 Cl1 84.38(5) . . ?
Cl4 Bi1 Cl1 172.80(5) . . ?
Cl10 Bi1 Cl5 84.69(5) . 2_656 ?
Cl9 Bi1 Cl5 174.69(5) . 2_656 ?
Cl4 Bi1 Cl5 93.74(5) . 2_656 ?
Cl1 Bi1 Cl5 91.56(5) . 2_656 ?
Cl10 Bi1 Cl5 167.80(5) . . ?
Cl9 Bi1 Cl5 99.84(5) . . ?
Cl4 Bi1 Cl5 85.89(5) . . ?
Cl1 Bi1 Cl5 89.87(5) . . ?
Cl5 Bi1 Cl5 83.52(5) 2_656 . ?
Cl2 Bi2 Cl8 91.57(5) . . ?
Cl2 Bi2 Cl6 91.87(5) . . ?
Cl8 Bi2 Cl6 90.32(6) . . ?
Cl2 Bi2 Cl7 93.59(5) . . ?
Cl8 Bi2 Cl7 82.27(5) . . ?
Cl6 Bi2 Cl7 170.91(5) . . ?
Cl2 Bi2 Cl3 83.61(5) . . ?
Cl8 Bi2 Cl3 170.00(5) . . ?
Cl6 Bi2 Cl3 98.56(6) . . ?
Cl7 Bi2 Cl3 89.28(5) . . ?
Cl2 Bi2 Cl3 166.06(6) . 2_567 ?
Cl8 Bi2 Cl3 102.21(5) . 2_567 ?
Cl6 Bi2 Cl3 86.00(5) . 2_567 ?
Cl7 Bi2 Cl3 90.40(5) . 2_567 ?
Cl3 Bi2 Cl3 83.09(5) . 2_567 ?
C20A C19A H19A 109.5 . . ?
C20A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C20A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C19A C20A C21A 118.6(18) . . ?
C19A C20A H20A 107.7 . . ?
C21A C20A H20A 107.7 . . ?
C19A C20A H20D 107.7 . . ?
C21A C20A H20D 107.7 . . ?
H20A C20A H20D 107.1 . . ?
C22A C21A C20A 113.1(19) . . ?
C22A C21A H21A 109.0 . . ?
C20A C21A H21A 109.0 . . ?
C22A C21A H21B 109.0 . . ?
C20A C21A H21B 109.0 . . ?
H21A C21A H21B 107.8 . . ?
C21A C22A N1 113.6(10) . . ?
C21A C22A H22A 108.8 . . ?
N1 C22A H22A 108.8 . . ?
C21A C22A H22B 108.8 . . ?
N1 C22A H22B 108.8 . . ?
H22A C22A H22B 107.7 . . ?
C20B C19B H19D 109.5 . . ?
C20B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C20B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C21B C20B C19B 110.6(9) . . ?
C21B C20B H20B 109.5 . . ?
C19B C20B H20B 109.5 . . ?
C21B C20B H20C 109.5 . . ?
C19B C20B H20C 109.5 . . ?
H20B C20B H20C 108.1 . . ?
C20B C21B C22B 116.6(8) . . ?
C20B C21B H21C 108.1 . . ?
C22B C21B H21C 108.1 . . ?
C20B C21B H21D 108.1 . . ?
C22B C21B H21D 108.1 . . ?
H21C C21B H21D 107.3 . . ?
N1 C22B C21B 108.5(6) . . ?
N1 C22B H22C 110.0 . . ?
C21B C22B H22C 110.0 . . ?
N1 C22B H22D 110.0 . . ?
C21B C22B H22D 110.0 . . ?
H22C C22B H22D 108.4 . . ?
N2 C33A C34A 111.6(6) . . ?
N2 C33A H33A 109.3 . . ?
C34A C33A H33A 109.3 . . ?
N2 C33A H33B 109.3 . . ?
C34A C33A H33B 109.3 . . ?
H33A C33A H33B 108.0 . . ?
C35A C34A C33A 130.4(10) . . ?
C35A C34A H34A 104.7 . . ?
C33A C34A H34A 104.7 . . ?
C35A C34A H34D 104.7 . . ?
C33A C34A H34D 104.7 . . ?
H34A C34A H34D 105.7 . . ?
C34A C35A C36A 98.6(18) . . ?
C34A C35A H35A 112.0 . . ?
C36A C35A H35A 112.0 . . ?
C34A C35A H35B 112.0 . . ?
C36A C35A H35B 112.0 . . ?
H35A C35A H35B 109.7 . . ?
C35A C36A H36A 109.5 . . ?
C35A C36A H36B 109.5 . . ?
H36A C36A H36B 109.5 . . ?
C35A C36A H36C 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
N2 C33B C34B 111.6(6) . . ?
N2 C33B H33C 109.3 . . ?
C34B C33B H33C 109.3 . . ?
N2 C33B H33D 109.3 . . ?
C34B C33B H33D 109.3 . . ?
H33C C33B H33D 108.0 . . ?
C33B C34B C35B 109.1(7) . . ?
C33B C34B H34B 109.9 . . ?
C35B C34B H34B 109.9 . . ?
C33B C34B H34C 109.9 . . ?
C35B C34B H34C 109.9 . . ?
H34B C34B H34C 108.3 . . ?
C36B C35B C34B 113.2(10) . . ?
C36B C35B H35C 108.9 . . ?
C34B C35B H35C 108.9 . . ?
C36B C35B H35D 108.9 . . ?
C34B C35B H35D 108.9 . . ?
H35C C35B H35D 107.7 . . ?
C35B C36B H36D 109.5 . . ?
C35B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
C35B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?

_refine_diff_density_max         2.358
_refine_diff_density_min         -1.555
_refine_diff_density_rms         0.165


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2003416'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2020-06-09 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT201_1                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          4 Report
RESPONSE: Disordering of the amyl groups
;
# Added during the CSD deposition process: Tuesday 09 June 2020 05:11 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H60 Bi2 Br10 N4'
_chemical_formula_weight         1813.98

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

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

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

_cell_length_a                   11.8794(4)
_cell_length_b                   12.0360(5)
_cell_length_c                   20.2002(7)
_cell_angle_alpha                92.755(3)
_cell_angle_beta                 105.010(3)
_cell_angle_gamma                104.720(3)
_cell_volume                     2678.00(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    7488
_cell_measurement_theta_min      3.5200
_cell_measurement_theta_max      29.1050

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.250
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    14.053
_shelx_estimated_absorpt_T_min   0.165
_shelx_estimated_absorpt_T_max   0.334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59341
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            25142
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.312
_diffrn_reflns_theta_max         29.615
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             12437
_reflns_number_gt                9131
_reflns_threshold_expression     >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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0040P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12437
_refine_ls_number_parameters     497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0568
_refine_ls_wR_factor_gt          0.0518
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0977(5) 0.9137(5) 0.3512(3) 0.0184(13) Uani 1 1 d . . . . .
H1A H 0.172313 0.961683 0.380333 0.022 Uiso 1 1 calc R U . . .
C2 C -0.1133(5) 0.8681(5) 0.3111(3) 0.0204(13) Uani 1 1 d . . . . .
H2A H -0.186891 0.884318 0.312691 0.025 Uiso 1 1 calc R U . . .
C3 C 0.0978(5) 0.8234(5) 0.3068(3) 0.0186(13) Uani 1 1 d . . . . .
H3A H 0.172425 0.808580 0.306323 0.022 Uiso 1 1 calc R U . . .
C4 C -0.0104(5) 0.7535(4) 0.2627(3) 0.0154(12) Uani 1 1 d . . . . .
N4 N 0.3885(4) 0.9915(4) 0.1450(3) 0.0282(13) Uani 1 1 d . . . . .
C5 C 0.0797(5) 0.5100(5) 0.1851(3) 0.0244(14) Uani 1 1 d . . . . .
H5A H 0.143520 0.473821 0.195421 0.029 Uiso 1 1 calc R U . . .
C6 C -0.1019(5) 0.5243(5) 0.1118(3) 0.0234(14) Uani 1 1 d . . . . .
H6A H -0.165474 0.497476 0.070170 0.028 Uiso 1 1 calc R U . . .
C7 C 0.0804(5) 0.6000(5) 0.2298(3) 0.0219(14) Uani 1 1 d . . . . .
H7A H 0.144987 0.625336 0.271067 0.026 Uiso 1 1 calc R U . . .
C8 C -0.1040(5) 0.6139(5) 0.1552(3) 0.0244(14) Uani 1 1 d . . . . .
H8A H -0.169106 0.648262 0.143727 0.029 Uiso 1 1 calc R U . . .
C9 C -0.0116(5) 0.6549(4) 0.2156(3) 0.0153(12) Uani 1 1 d . . . . .
C10 C -0.1169(5) 0.7780(5) 0.2661(3) 0.0204(13) Uani 1 1 d . . . . .
H10A H -0.192584 0.731933 0.236946 0.024 Uiso 1 1 calc R U . . .
C11 C -0.0041(5) 1.0305(5) 0.4037(3) 0.0218(14) Uani 1 1 d . . . . .
H11A H 0.066716 1.040706 0.444408 0.026 Uiso 1 1 calc R U . . .
H11B H -0.078095 1.008933 0.419532 0.026 Uiso 1 1 calc R U . . .
C12 C 0.0033(5) 1.1451(5) 0.3738(3) 0.0251(15) Uani 1 1 d . . . . .
H12A H -0.070665 1.136041 0.335201 0.030 Uiso 1 1 calc R U . . .
H12B H 0.003968 1.204232 0.409839 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1131(5) 1.1893(5) 0.3477(3) 0.0298(16) Uani 1 1 d . . . . .
H13A H 0.104757 1.138186 0.305791 0.036 Uiso 1 1 calc R U . . .
H13B H 0.186425 1.184826 0.383257 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6110(5) 0.3356(5) 0.4344(3) 0.0248(15) Uani 1 1 d . . . . .
H14A H 0.652902 0.278164 0.444232 0.030 Uiso 1 1 calc R U . . .
C15 C 0.1305(6) 1.3139(5) 0.3305(4) 0.0395(18) Uani 1 1 d . . . . .
H15A H 0.195707 1.332949 0.307308 0.047 Uiso 1 1 calc R U . . .
H15B H 0.054825 1.319734 0.297741 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5792(5) 0.3863(5) 0.4865(3) 0.0232(14) Uani 1 1 d . . . . .
H16A H 0.597780 0.363261 0.531506 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5268(5) 0.4468(5) 0.3555(3) 0.0268(15) Uani 1 1 d . . . . .
H17A H 0.508839 0.467216 0.309862 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5192(5) 0.4725(5) 0.4727(3) 0.0201(13) Uani 1 1 d . . . . .
C19 C 0.1630(6) 1.4025(5) 0.3940(4) 0.048(2) Uani 1 1 d . . . . .
H19A H 0.172994 1.480297 0.379859 0.072 Uiso 1 1 calc R U . . .
H19B H 0.098017 1.385354 0.416705 0.072 Uiso 1 1 calc R U . . .
H19C H 0.238989 1.398577 0.426278 0.072 Uiso 1 1 calc R U . . .
C21 C 0.8647(6) 0.5122(5) 0.4129(3) 0.0356(17) Uani 1 1 d . . . . .
H21A H 0.894432 0.459523 0.444961 0.043 Uiso 1 1 calc R U . . .
H21B H 0.792596 0.526742 0.423672 0.043 Uiso 1 1 calc R U . . .
C22 C 0.4935(5) 0.5010(5) 0.4050(3) 0.0277(15) Uani 1 1 d . . . . .
H22A H 0.452552 0.558784 0.393502 0.033 Uiso 1 1 calc R U . . .
C24 C 0.7556(5) 0.3269(5) 0.3283(3) 0.0269(15) Uani 1 1 d . . . . .
H24A H 0.770465 0.288033 0.288324 0.032 Uiso 1 1 calc R U . . .
H24B H 0.786259 0.290036 0.369362 0.032 Uiso 1 1 calc R U . . .
C25 C 0.8289(5) 0.4549(5) 0.3398(3) 0.0310(16) Uani 1 1 d . . . . .
H25A H 0.903479 0.460747 0.325237 0.037 Uiso 1 1 calc R U . . .
H25B H 0.780465 0.498324 0.309462 0.037 Uiso 1 1 calc R U . . .
C26 C 0.6195(5) 0.3060(5) 0.3152(3) 0.0254(15) Uani 1 1 d . . . . .
H26A H 0.586727 0.333482 0.270755 0.030 Uiso 1 1 calc R U . . .
H26B H 0.581262 0.221715 0.310766 0.030 Uiso 1 1 calc R U . . .
C28 C 0.4769(5) 0.9984(5) 0.0314(3) 0.0222(14) Uani 1 1 d . . . . .
C30 C 0.9637(5) 0.6269(5) 0.4242(3) 0.0356(17) Uani 1 1 d . . . . .
H30A H 0.984764 0.661698 0.472179 0.053 Uiso 1 1 calc R U . . .
H30B H 1.035794 0.612562 0.414413 0.053 Uiso 1 1 calc R U . . .
H30C H 0.934023 0.679738 0.393138 0.053 Uiso 1 1 calc R U . . .
C31 C 0.3258(6) 0.9838(6) 0.2003(3) 0.0395(18) Uani 1 1 d . . . . .
H31A H 0.372631 1.046680 0.238350 0.047 Uiso 1 1 calc R U . A 3
H31B H 0.324183 0.909176 0.219169 0.047 Uiso 1 1 calc R U . A 3
C32 C 0.4058(6) 1.0869(5) 0.1143(4) 0.0400(19) Uani 1 1 d . . . . .
H32A H 0.387071 1.152543 0.131815 0.048 Uiso 1 1 calc R U . . .
C33 C 0.4170(6) 0.8987(5) 0.1217(4) 0.0387(18) Uani 1 1 d . . . . .
H33A H 0.407038 0.831096 0.144467 0.046 Uiso 1 1 calc R U . . .
C34 C 0.4602(6) 0.9018(5) 0.0655(4) 0.0400(18) Uani 1 1 d . . . . .
H34A H 0.479356 0.835492 0.049228 0.048 Uiso 1 1 calc R U . . .
C35 C 0.4502(6) 1.0930(5) 0.0574(4) 0.0359(17) Uani 1 1 d . . . . .
H35A H 0.462260 1.162326 0.036330 0.043 Uiso 1 1 calc R U . . .
C44 C -0.0142(5) 0.3741(5) 0.0787(3) 0.0361(18) Uani 1 1 d . . . . .
H44A H 0.065840 0.357970 0.089464 0.043 Uiso 1 1 calc R U . B 1
H44B H -0.035953 0.391122 0.030337 0.043 Uiso 1 1 calc R U . B 1
N1 N -0.0071(4) 0.9347(4) 0.3535(2) 0.0186(11) Uani 1 1 d . . . . .
N2 N -0.0114(4) 0.4734(4) 0.1271(2) 0.0225(12) Uani 1 1 d . . . . .
N3 N 0.5846(4) 0.3646(4) 0.3704(2) 0.0206(11) Uani 1 1 d . . . . .
Br3 Br 0.78655(5) 1.12680(5) 0.48446(3) 0.02015(13) Uani 1 1 d . . . . .
Br4 Br 0.61445(5) 0.65583(5) 0.04103(3) 0.02170(13) Uani 1 1 d . . . . .
Br5 Br 0.38030(5) 0.74928(5) 0.35011(3) 0.02527(14) Uani 1 1 d . . . . .
Br6 Br 0.73280(5) 0.78643(5) 0.44258(3) 0.02424(14) Uani 1 1 d . . . . .
Br7 Br 0.31192(5) 0.33663(5) 0.17162(3) 0.02549(14) Uani 1 1 d . . . . .
Br8 Br 0.41785(5) 1.08299(5) 0.42076(3) 0.02236(14) Uani 1 1 d . . . . .
Br9 Br 0.62140(5) 0.98741(5) 0.30151(3) 0.02432(14) Uani 1 1 d . . . . .
Br10 Br 0.63412(5) 0.37527(5) 0.14185(3) 0.02778(15) Uani 1 1 d . . . . .
Br11 Br 0.55224(5) 0.64548(5) 0.22054(3) 0.02895(15) Uani 1 1 d . . . . .
Br12 Br 0.25844(5) 0.59909(5) 0.07025(3) 0.02967(15) Uani 1 1 d . . . . .
Bi1 Bi 0.45662(2) 0.49431(2) 0.10619(2) 0.01871(6) Uani 1 1 d . . . . .
Bi2 Bi 0.58829(2) 0.93398(2) 0.42645(2) 0.01596(5) Uani 1 1 d . . . . .
C1A C -0.1107(14) 0.2273(13) 0.1647(8) 0.023(4) Uiso 0.4 1 d . . P C 1
H1A1 H -0.108315 0.296248 0.194396 0.028 Uiso 0.4 1 calc R U P C 1
H1A2 H -0.032390 0.208912 0.181836 0.028 Uiso 0.4 1 calc R U P C 1
C2A C -0.2146(14) 0.1236(13) 0.1714(9) 0.032(4) Uiso 0.4 1 d . . P C 1
H2AA H -0.207645 0.118748 0.221016 0.039 Uiso 0.4 1 calc R U P C 1
H2AB H -0.293227 0.139037 0.150053 0.039 Uiso 0.4 1 calc R U P C 1
C3A C -0.2151(17) 0.0113(15) 0.1392(11) 0.045(5) Uiso 0.4 1 d . . P C 1
H3AA H -0.282768 -0.049318 0.145577 0.067 Uiso 0.4 1 calc R U P C 1
H3AB H -0.224214 0.014331 0.089749 0.067 Uiso 0.4 1 calc R U P C 1
H3AC H -0.138496 -0.005990 0.160823 0.067 Uiso 0.4 1 calc R U P C 1
C43A C -0.1248(14) 0.2562(13) 0.0914(9) 0.016(4) Uiso 0.4 1 d . . P C 1
H43A H -0.204797 0.271281 0.074309 0.020 Uiso 0.4 1 calc R U P C 1
H43B H -0.125860 0.186958 0.062474 0.020 Uiso 0.4 1 calc R U P C 1
C1B C -0.1011(9) 0.2130(8) 0.1320(6) 0.018(2) Uiso 0.6 1 d . . P C 2
H1BA H -0.102120 0.264047 0.171624 0.022 Uiso 0.6 1 calc R U P C 2
H1BB H -0.022673 0.193593 0.143640 0.022 Uiso 0.6 1 calc R U P C 2
C2B C -0.2045(9) 0.1021(9) 0.1199(5) 0.030(3) Uiso 0.6 1 d . . P C 2
H2BA H -0.205981 0.053703 0.078467 0.036 Uiso 0.6 1 calc R U P C 2
H2BB H -0.282304 0.122532 0.110379 0.036 Uiso 0.6 1 calc R U P C 2
C3B C -0.1939(11) 0.0308(11) 0.1814(7) 0.045(3) Uiso 0.6 1 d . . P C 2
H3BA H -0.262589 -0.038943 0.170510 0.067 Uiso 0.6 1 calc R U P C 2
H3BB H -0.117960 0.008560 0.190502 0.067 Uiso 0.6 1 calc R U P C 2
H3BC H -0.194344 0.077445 0.222439 0.067 Uiso 0.6 1 calc R U P C 2
C43B C -0.1124(10) 0.2763(9) 0.0687(6) 0.020(3) Uiso 0.6 1 d . . P C 2
H43C H -0.116115 0.223784 0.028428 0.024 Uiso 0.6 1 calc R U P C 2
H43D H -0.188609 0.299732 0.058614 0.024 Uiso 0.6 1 calc R U P C 2
C4A C 0.1988(7) 0.9929(8) 0.1753(4) 0.025(2) Uiso 0.7 1 d . . P D 3
H40A H 0.200413 1.070372 0.160514 0.030 Uiso 0.7 1 calc R U P D 3
H40B H 0.160750 0.984523 0.213694 0.030 Uiso 0.7 1 calc R U P D 3
C5A C 0.1203(10) 0.8970(10) 0.1130(6) 0.031(3) Uiso 0.7 1 d . . P D 3
H5A1 H 0.154262 0.908939 0.073216 0.038 Uiso 0.7 1 calc R U P D 3
H5A2 H 0.123277 0.819593 0.126595 0.038 Uiso 0.7 1 calc R U P D 3
C6A C -0.0105(9) 0.9026(9) 0.0924(5) 0.037(3) Uiso 0.7 1 d . . P D 3
H6A1 H -0.010238 0.984865 0.097867 0.044 Uiso 0.7 1 calc R U P D 3
H6A2 H -0.051519 0.863036 0.125096 0.044 Uiso 0.7 1 calc R U P D 3
C7A C -0.0892(11) 0.8473(10) 0.0159(6) 0.050(3) Uiso 0.7 1 d . . P D 3
H7A1 H -0.046251 0.880105 -0.017102 0.075 Uiso 0.7 1 calc R U P D 3
H7A2 H -0.167836 0.864419 0.006072 0.075 Uiso 0.7 1 calc R U P D 3
H7A3 H -0.101921 0.763233 0.011737 0.075 Uiso 0.7 1 calc R U P D 3
C4B C 0.190(3) 0.905(3) 0.1613(16) 0.066(8) Uiso 0.3 1 d . . P D 4
H4B1 H 0.196940 0.825544 0.152579 0.079 Uiso 0.3 1 calc R U P D 4
H4B2 H 0.143027 0.902249 0.195217 0.079 Uiso 0.3 1 calc R U P D 4
C5B C 0.117(2) 0.928(2) 0.0986(12) 0.024(7) Uiso 0.3 1 d . . P D 4
H5B1 H 0.158156 0.923127 0.062121 0.029 Uiso 0.3 1 calc R U P D 4
H5B2 H 0.111847 1.008380 0.104855 0.029 Uiso 0.3 1 calc R U P D 4
C6B C -0.011(2) 0.848(2) 0.0733(14) 0.040(7) Uiso 0.3 1 d . . P D 4
H6B1 H -0.004949 0.783321 0.101637 0.048 Uiso 0.3 1 calc R U P D 4
H6B2 H -0.057013 0.890808 0.093842 0.048 Uiso 0.3 1 calc R U P D 4
C7B C -0.0750(19) 0.8054(18) 0.0288(11) 0.019(5) Uiso 0.3 1 d . . P D 4
H7B1 H -0.057779 0.843478 -0.010641 0.028 Uiso 0.3 1 calc R U P D 4
H7B2 H -0.155566 0.807452 0.031653 0.028 Uiso 0.3 1 calc R U P D 4
H7B3 H -0.072750 0.724724 0.022933 0.028 Uiso 0.3 1 calc R U P D 4


_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 N1 1.343(7) . ?
C1 C3 1.375(7) . ?
C1 H1A 0.9500 . ?
C2 N1 1.353(6) . ?
C2 C10 1.368(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.393(7) . ?
C3 H3A 0.9500 . ?
C4 C10 1.387(7) . ?
C4 C9 1.479(7) . ?
N4 C32 1.327(8) . ?
N4 C33 1.344(7) . ?
N4 C31 1.490(8) . ?
C5 N2 1.338(7) . ?
C5 C7 1.372(7) . ?
C5 H5A 0.9500 . ?
C6 N2 1.345(7) . ?
C6 C8 1.366(7) . ?
C6 H6A 0.9500 . ?
C7 C9 1.392(7) . ?
C7 H7A 0.9500 . ?
C8 C9 1.383(7) . ?
C8 H8A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 N1 1.485(6) . ?
C11 C12 1.523(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.531(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N3 1.335(7) . ?
C14 C16 1.372(8) . ?
C14 H14A 0.9500 . ?
C15 C19 1.528(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.400(7) . ?
C16 H16A 0.9500 . ?
C17 N3 1.345(7) . ?
C17 C22 1.362(8) . ?
C17 H17A 0.9500 . ?
C18 C22 1.402(8) . ?
C18 C18 1.485(11) 2_666 ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C25 1.507(8) . ?
C21 C30 1.532(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9500 . ?
C24 C26 1.521(7) . ?
C24 C25 1.538(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 N3 1.491(7) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C28 C35 1.372(8) . ?
C28 C34 1.376(9) . ?
C28 C28 1.506(12) 2_675 ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C4A 1.496(10) . ?
C31 C4B 1.61(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C35 1.381(9) . ?
C32 H32A 0.9500 . ?
C33 C34 1.361(9) . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
C35 H35A 0.9500 . ?
C44 C43B 1.395(11) . ?
C44 N2 1.494(7) . ?
C44 C43A 1.752(16) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
Br3 Bi2 2.7996(6) . ?
Br4 Bi1 2.9494(6) . ?
Br4 Bi1 3.1986(6) 2_665 ?
Br5 Bi2 2.8862(6) . ?
Br6 Bi2 2.7427(6) . ?
Br7 Bi1 2.8395(6) . ?
Br8 Bi2 3.0122(6) . ?
Br8 Bi2 3.1213(6) 2_676 ?
Br9 Bi2 2.7347(6) . ?
Br10 Bi1 2.8046(7) . ?
Br11 Bi1 2.6688(6) . ?
Br12 Bi1 2.8933(7) . ?
C1A C43A 1.51(2) . ?
C1A C2A 1.55(2) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A C3A 1.47(2) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C43A H43A 0.9900 . ?
C43A H43B 0.9900 . ?
C1B C43B 1.514(14) . ?
C1B C2B 1.525(13) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B C3B 1.541(16) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B H3BA 0.9800 . ?
C3B H3BB 0.9800 . ?
C3B H3BC 0.9800 . ?
C43B H43C 0.9900 . ?
C43B H43D 0.9900 . ?
C4A C5A 1.578(13) . ?
C4A H40A 0.9900 . ?
C4A H40B 0.9900 . ?
C5A C6A 1.522(15) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A C7A 1.594(15) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C4B C5B 1.42(4) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B C6B 1.52(3) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B C7B 1.02(3) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C3 120.5(5) . . ?
N1 C1 H1A 119.7 . . ?
C3 C1 H1A 119.7 . . ?
N1 C2 C10 121.3(5) . . ?
N1 C2 H2A 119.4 . . ?
C10 C2 H2A 119.4 . . ?
C1 C3 C4 120.6(5) . . ?
C1 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C10 C4 C3 117.4(5) . . ?
C10 C4 C9 121.4(5) . . ?
C3 C4 C9 121.1(5) . . ?
C32 N4 C33 119.9(6) . . ?
C32 N4 C31 119.5(6) . . ?
C33 N4 C31 120.3(6) . . ?
N2 C5 C7 119.7(5) . . ?
N2 C5 H5A 120.2 . . ?
C7 C5 H5A 120.2 . . ?
N2 C6 C8 121.1(5) . . ?
N2 C6 H6A 119.5 . . ?
C8 C6 H6A 119.5 . . ?
C5 C7 C9 121.2(5) . . ?
C5 C7 H7A 119.4 . . ?
C9 C7 H7A 119.4 . . ?
C6 C8 C9 120.3(6) . . ?
C6 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C8 C9 C7 117.0(5) . . ?
C8 C9 C4 121.3(5) . . ?
C7 C9 C4 121.6(5) . . ?
C2 C10 C4 120.2(5) . . ?
C2 C10 H10A 119.9 . . ?
C4 C10 H10A 119.9 . . ?
N1 C11 C12 113.3(5) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 114.7(5) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C15 113.3(5) . . ?
C12 C13 H13A 108.9 . . ?
C15 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C15 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N3 C14 C16 121.9(6) . . ?
N3 C14 H14A 119.0 . . ?
C16 C14 H14A 119.0 . . ?
C19 C15 C13 113.2(6) . . ?
C19 C15 H15A 108.9 . . ?
C13 C15 H15A 108.9 . . ?
C19 C15 H15B 108.9 . . ?
C13 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C14 C16 C18 119.3(6) . . ?
C14 C16 H16A 120.3 . . ?
C18 C16 H16A 120.3 . . ?
N3 C17 C22 120.9(6) . . ?
N3 C17 H17A 119.6 . . ?
C22 C17 H17A 119.6 . . ?
C16 C18 C22 117.2(5) . . ?
C16 C18 C18 121.0(7) . 2_666 ?
C22 C18 C18 121.8(7) . 2_666 ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C21 C30 111.6(5) . . ?
C25 C21 H21A 109.3 . . ?
C30 C21 H21A 109.3 . . ?
C25 C21 H21B 109.3 . . ?
C30 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C17 C22 C18 120.6(6) . . ?
C17 C22 H22A 119.7 . . ?
C18 C22 H22A 119.7 . . ?
C26 C24 C25 115.0(5) . . ?
C26 C24 H24A 108.5 . . ?
C25 C24 H24A 108.5 . . ?
C26 C24 H24B 108.5 . . ?
C25 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
C21 C25 C24 115.1(5) . . ?
C21 C25 H25A 108.5 . . ?
C24 C25 H25A 108.5 . . ?
C21 C25 H25B 108.5 . . ?
C24 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
N3 C26 C24 114.0(5) . . ?
N3 C26 H26A 108.7 . . ?
C24 C26 H26A 108.7 . . ?
N3 C26 H26B 108.7 . . ?
C24 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C35 C28 C34 117.1(6) . . ?
C35 C28 C28 120.9(7) . 2_675 ?
C34 C28 C28 122.0(7) . 2_675 ?
C21 C30 H30A 109.5 . . ?
C21 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C21 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N4 C31 C4A 112.9(6) . . ?
N4 C31 C4B 103.2(11) . . ?
N4 C31 H31A 109.0 . . ?
C4A C31 H31A 109.0 . . ?
N4 C31 H31B 109.0 . . ?
C4A C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
N4 C32 C35 121.6(6) . . ?
N4 C32 H32A 119.2 . . ?
C35 C32 H32A 119.2 . . ?
N4 C33 C34 119.9(6) . . ?
N4 C33 H33A 120.1 . . ?
C34 C33 H33A 120.1 . . ?
C33 C34 C28 121.8(6) . . ?
C33 C34 H34A 119.1 . . ?
C28 C34 H34A 119.1 . . ?
C28 C35 C32 119.7(6) . . ?
C28 C35 H35A 120.2 . . ?
C32 C35 H35A 120.2 . . ?
C43B C44 N2 116.1(6) . . ?
N2 C44 C43A 105.5(6) . . ?
N2 C44 H44A 110.7 . . ?
C43A C44 H44A 110.7 . . ?
N2 C44 H44B 110.7 . . ?
C43A C44 H44B 110.7 . . ?
H44A C44 H44B 108.8 . . ?
C1 N1 C2 120.0(5) . . ?
C1 N1 C11 119.1(5) . . ?
C2 N1 C11 121.0(5) . . ?
C5 N2 C6 120.7(5) . . ?
C5 N2 C44 120.1(5) . . ?
C6 N2 C44 119.2(5) . . ?
C14 N3 C17 120.1(5) . . ?
C14 N3 C26 120.1(5) . . ?
C17 N3 C26 119.8(5) . . ?
Bi1 Br4 Bi1 98.636(17) . 2_665 ?
Bi2 Br8 Bi2 94.294(17) . 2_676 ?
Br11 Bi1 Br10 93.72(2) . . ?
Br11 Bi1 Br7 92.088(19) . . ?
Br10 Bi1 Br7 88.609(19) . . ?
Br11 Bi1 Br12 88.42(2) . . ?
Br10 Bi1 Br12 175.084(19) . . ?
Br7 Bi1 Br12 86.891(19) . . ?
Br11 Bi1 Br4 87.352(18) . . ?
Br10 Bi1 Br4 89.499(18) . . ?
Br7 Bi1 Br4 177.99(2) . . ?
Br12 Bi1 Br4 95.023(19) . . ?
Br11 Bi1 Br4 168.459(18) . 2_665 ?
Br10 Bi1 Br4 83.810(18) . 2_665 ?
Br7 Bi1 Br4 99.107(17) . 2_665 ?
Br12 Bi1 Br4 94.946(17) . 2_665 ?
Br4 Bi1 Br4 81.365(17) . 2_665 ?
Br9 Bi2 Br6 94.042(19) . . ?
Br9 Bi2 Br3 86.180(18) . . ?
Br6 Bi2 Br3 92.252(18) . . ?
Br9 Bi2 Br5 86.831(19) . . ?
Br6 Bi2 Br5 91.042(18) . . ?
Br3 Bi2 Br5 172.47(2) . . ?
Br9 Bi2 Br8 92.032(18) . . ?
Br6 Bi2 Br8 173.598(19) . . ?
Br3 Bi2 Br8 90.164(17) . . ?
Br5 Bi2 Br8 87.275(17) . . ?
Br9 Bi2 Br8 169.724(18) . 2_676 ?
Br6 Bi2 Br8 88.661(18) . 2_676 ?
Br3 Bi2 Br8 83.807(17) . 2_676 ?
Br5 Bi2 Br8 103.048(18) . 2_676 ?
Br8 Bi2 Br8 85.706(17) . 2_676 ?
C43A C1A C2A 113.3(13) . . ?
C43A C1A H1A1 108.9 . . ?
C2A C1A H1A1 108.9 . . ?
C43A C1A H1A2 108.9 . . ?
C2A C1A H1A2 108.9 . . ?
H1A1 C1A H1A2 107.7 . . ?
C3A C2A C1A 114.4(14) . . ?
C3A C2A H2AA 108.7 . . ?
C1A C2A H2AA 108.7 . . ?
C3A C2A H2AB 108.7 . . ?
C1A C2A H2AB 108.7 . . ?
H2AA C2A H2AB 107.6 . . ?
C2A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
C2A C3A H3AC 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C1A C43A C44 116.8(11) . . ?
C1A C43A H43A 108.1 . . ?
C44 C43A H43A 108.1 . . ?
C1A C43A H43B 108.1 . . ?
C44 C43A H43B 108.1 . . ?
H43A C43A H43B 107.3 . . ?
C43B C1B C2B 111.2(9) . . ?
C43B C1B H1BA 109.4 . . ?
C2B C1B H1BA 109.4 . . ?
C43B C1B H1BB 109.4 . . ?
C2B C1B H1BB 109.4 . . ?
H1BA C1B H1BB 108.0 . . ?
C1B C2B C3B 113.4(9) . . ?
C1B C2B H2BA 108.9 . . ?
C3B C2B H2BA 108.9 . . ?
C1B C2B H2BB 108.9 . . ?
C3B C2B H2BB 108.9 . . ?
H2BA C2B H2BB 107.7 . . ?
C2B C3B H3BA 109.5 . . ?
C2B C3B H3BB 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
C2B C3B H3BC 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
C44 C43B C1B 110.9(8) . . ?
C44 C43B H43C 109.5 . . ?
C1B C43B H43C 109.5 . . ?
C44 C43B H43D 109.5 . . ?
C1B C43B H43D 109.5 . . ?
H43C C43B H43D 108.0 . . ?
C31 C4A C5A 111.5(7) . . ?
C31 C4A H40A 109.3 . . ?
C5A C4A H40A 109.3 . . ?
C31 C4A H40B 109.3 . . ?
C5A C4A H40B 109.3 . . ?
H40A C4A H40B 108.0 . . ?
C6A C5A C4A 110.2(8) . . ?
C6A C5A H5A1 109.6 . . ?
C4A C5A H5A1 109.6 . . ?
C6A C5A H5A2 109.6 . . ?
C4A C5A H5A2 109.6 . . ?
H5A1 C5A H5A2 108.1 . . ?
C5A C6A C7A 116.3(9) . . ?
C5A C6A H6A1 108.2 . . ?
C7A C6A H6A1 108.2 . . ?
C5A C6A H6A2 108.2 . . ?
C7A C6A H6A2 108.2 . . ?
H6A1 C6A H6A2 107.4 . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C5B C4B C31 124(2) . . ?
C5B C4B H4B1 106.3 . . ?
C31 C4B H4B1 106.3 . . ?
C5B C4B H4B2 106.3 . . ?
C31 C4B H4B2 106.3 . . ?
H4B1 C4B H4B2 106.4 . . ?
C4B C5B C6B 115(2) . . ?
C4B C5B H5B1 108.4 . . ?
C6B C5B H5B1 108.4 . . ?
C4B C5B H5B2 108.4 . . ?
C6B C5B H5B2 108.4 . . ?
H5B1 C5B H5B2 107.5 . . ?
C7B C6B C5B 141(3) . . ?
C7B C6B H6B1 101.7 . . ?
C5B C6B H6B1 101.7 . . ?
C7B C6B H6B2 101.7 . . ?
C5B C6B H6B2 101.7 . . ?
H6B1 C6B H6B2 104.7 . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?

_refine_diff_density_max         1.502
_refine_diff_density_min         -1.830
_refine_diff_density_rms         0.209


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 2003415'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H59 Bi2 Cl10 N4'
_chemical_formula_weight         1368.37

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

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

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

_cell_length_a                   11.2548(5)
_cell_length_b                   11.3269(7)
_cell_length_c                   11.4527(6)
_cell_angle_alpha                77.607(5)
_cell_angle_beta                 69.581(5)
_cell_angle_gamma                68.028(5)
_cell_volume                     1262.94(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5927
_cell_measurement_theta_min      3.7380
_cell_measurement_theta_max      29.3070

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_F_000             663
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    7.519
_shelx_estimated_absorpt_T_min   0.398
_shelx_estimated_absorpt_T_max   0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72945
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            9986
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.470
_diffrn_reflns_theta_max         29.535
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5892
_reflns_number_gt                5332
_reflns_threshold_expression     >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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5892
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0461
_refine_ls_wR_factor_gt          0.0438
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.1128(5) 0.8180(5) 1.1030(4) 0.0566(14) Uani 1 1 d . . . . .
H1A H 0.126494 0.744842 1.166245 0.085 Uiso 1 1 calc R U . . .
H1B H 0.091017 0.896830 1.139826 0.085 Uiso 1 1 calc R U . . .
H1C H 0.038789 0.823401 1.073570 0.085 Uiso 1 1 calc R U . . .
C2 C 0.2388(4) 0.8012(4) 0.9945(4) 0.0300(10) Uani 1 1 d . . . . .
H2A H 0.261206 0.720230 0.959506 0.036 Uiso 1 1 calc R U . . .
H2B H 0.313372 0.793573 1.025684 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2286(4) 0.9103(4) 0.8901(3) 0.0267(9) Uani 1 1 d . . . . .
H3A H 0.154536 0.918213 0.858039 0.032 Uiso 1 1 calc R U . . .
H3B H 0.207022 0.991578 0.924216 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3579(3) 0.8886(4) 0.7832(3) 0.0227(9) Uani 1 1 d . . . . .
H4A H 0.380897 0.804979 0.752768 0.027 Uiso 1 1 calc R U . . .
H4B H 0.430607 0.883299 0.815848 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3541(3) 0.9905(4) 0.6731(3) 0.0215(8) Uani 1 1 d . . . . .
H5A H 0.332422 1.074592 0.701961 0.026 Uiso 1 1 calc R U . . .
H5B H 0.443609 0.970896 0.609946 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1427(4) 1.1007(4) 0.6211(3) 0.0217(8) Uani 1 1 d . . . . .
H6A H 0.133994 1.172892 0.656923 0.026 Uiso 1 1 calc R U . . .
C7 C 0.0435(4) 1.1042(4) 0.5767(3) 0.0218(8) Uani 1 1 d . . . . .
H7A H -0.033433 1.178580 0.581789 0.026 Uiso 1 1 calc R U . . .
C8 C 0.0546(3) 0.9987(4) 0.5235(3) 0.0172(8) Uani 1 1 d . . . . .
C9 C 0.1697(4) 0.8946(4) 0.5165(3) 0.0245(9) Uani 1 1 d . . . . .
H9A H 0.181531 0.821661 0.479913 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2674(4) 0.8952(4) 0.5617(3) 0.0238(9) Uani 1 1 d . . . . .
H10A H 0.346611 0.823075 0.555409 0.029 Uiso 1 1 calc R U . . .
C16 C 0.2789(4) 0.4080(4) -0.0048(3) 0.0309(10) Uani 1 1 d . . . . .
H16A H 0.245649 0.385950 -0.059856 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3910(4) 0.4453(4) -0.0528(3) 0.0254(9) Uani 1 1 d . . . . .
H17A H 0.435091 0.447571 -0.140309 0.031 Uiso 1 1 calc R U . . .
C18 C 0.4399(4) 0.4795(4) 0.0254(3) 0.0204(8) Uani 1 1 d . . . . .
C19 C 0.3703(4) 0.4738(4) 0.1530(3) 0.0367(12) Uani 1 1 d . . . . .
H19A H 0.400291 0.496713 0.210097 0.044 Uiso 1 1 calc R U . . .
C20 C 0.2598(4) 0.4357(4) 0.1965(4) 0.0353(11) Uani 1 1 d . . . . .
H20A H 0.213504 0.432945 0.283559 0.042 Uiso 1 1 calc R U . . .
C1B C 0.1460(8) 0.2148(8) 0.1493(8) 0.035(2) Uiso 0.5 1 d . . P A 1
H1BA H 0.168959 0.208253 0.058673 0.042 Uiso 0.5 1 calc R U P A 1
H1BB H 0.069502 0.182627 0.192963 0.042 Uiso 0.5 1 calc R U P A 1
C2B C 0.3363(10) -0.0087(10) 0.2190(9) 0.038(2) Uiso 0.5 1 d . . P A 1
H2BA H 0.294226 -0.047595 0.296588 0.046 Uiso 0.5 1 calc R U P A 1
C11B C 0.4639(9) -0.0986(10) 0.1418(9) 0.039(2) Uiso 0.5 1 d . . P A 1
H11A H 0.481836 -0.184386 0.186602 0.059 Uiso 0.5 1 calc R U P A 1
H11B H 0.453620 -0.101723 0.061124 0.059 Uiso 0.5 1 calc R U P A 1
H11C H 0.538859 -0.067786 0.127679 0.059 Uiso 0.5 1 calc R U P A 1
C13B C 0.2658(10) 0.1290(10) 0.1947(10) 0.033(3) Uiso 0.5 1 d . . P A 1
H13A H 0.339329 0.159904 0.136834 0.040 Uiso 0.5 1 calc R U P A 1
H13B H 0.245388 0.161768 0.275390 0.040 Uiso 0.5 1 calc R U P A 1
C15B C 0.1039(4) 0.3484(4) 0.1691(4) 0.0309(9) Uiso 0.5 1 d . . P A 1
H15A H 0.064730 0.357358 0.259945 0.037 Uiso 0.5 1 calc R U P A 1
H15B H 0.033049 0.398347 0.128509 0.037 Uiso 0.5 1 calc R U P A 1
C1A C 0.1585(7) 0.2122(8) 0.2341(7) 0.0240(17) Uiso 0.5 1 d . . P A 2
H1AA H 0.182678 0.220880 0.306307 0.029 Uiso 0.5 1 calc R U P A 2
H1AB H 0.085352 0.174469 0.267306 0.029 Uiso 0.5 1 calc R U P A 2
C2A C 0.3057(8) -0.0093(9) 0.1745(9) 0.032(2) Uiso 0.5 1 d . . P A 2
H2AA H 0.302040 -0.040818 0.102075 0.039 Uiso 0.5 1 calc R U P A 2
H2AB H 0.232936 -0.025716 0.248027 0.039 Uiso 0.5 1 calc R U P A 2
C11A C 0.4395(10) -0.0880(10) 0.1994(10) 0.042(3) Uiso 0.5 1 d . . P A 2
H11D H 0.447408 -0.178752 0.215031 0.063 Uiso 0.5 1 calc R U P A 2
H11E H 0.513158 -0.075464 0.126368 0.063 Uiso 0.5 1 calc R U P A 2
H11F H 0.443826 -0.060312 0.272801 0.063 Uiso 0.5 1 calc R U P A 2
C13A C 0.2798(9) 0.1197(9) 0.1510(9) 0.027(2) Uiso 0.5 1 d . . P A 2
H13C H 0.272756 0.143532 0.064723 0.033 Uiso 0.5 1 calc R U P A 2
H13D H 0.360093 0.136615 0.150633 0.033 Uiso 0.5 1 calc R U P A 2
C15A C 0.1039(4) 0.3484(4) 0.1691(4) 0.0309(9) Uiso 0.5 1 d . . P A 2
H15C H 0.072057 0.343265 0.100480 0.037 Uiso 0.5 1 calc R U P A 2
H15D H 0.027978 0.403428 0.230125 0.037 Uiso 0.5 1 calc R U P A 2
N1 N 0.2522(3) 0.9971(3) 0.6150(3) 0.0181(7) Uani 1 1 d . . . . .
N2 N 0.2158(3) 0.4021(3) 0.1185(3) 0.0237(7) Uani 1 1 d . . . . .
Cl1 Cl 0.42364(8) 0.61837(9) 0.38361(8) 0.01990(19) Uani 1 1 d . . . . .
Cl2 Cl 0.77479(9) 0.36065(9) 0.25833(8) 0.0236(2) Uani 1 1 d . . . . .
Cl3 Cl 0.82499(9) 0.66760(9) 0.22497(8) 0.0251(2) Uani 1 1 d . . . . .
Cl4 Cl 0.90059(9) 0.42155(9) 0.49088(9) 0.0257(2) Uani 1 1 d . . . . .
Cl5 Cl 0.63168(9) 0.73274(9) 0.54901(9) 0.0263(2) Uani 1 1 d . . . . .
Bi1 Bi 0.69677(2) 0.53648(2) 0.41474(2) 0.01441(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.503(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.526(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.515(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.517(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.488(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.339(5) . ?
C6 C7 1.364(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.401(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.378(5) . ?
C8 C8 1.492(6) 2_576 ?
C9 C10 1.372(5) . ?
C9 H9A 0.9500 . ?
C10 N1 1.347(4) . ?
C10 H10A 0.9500 . ?
C16 N2 1.341(4) . ?
C16 C17 1.373(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.382(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.397(5) . ?
C18 C18 1.480(6) 2_665 ?
C19 C20 1.362(5) . ?
C19 H19A 0.9500 . ?
C20 N2 1.336(4) . ?
C20 H20A 0.9500 . ?
C1B C15B 1.449(9) . ?
C1B C13B 1.525(13) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B C13B 1.478(14) . ?
C2B C11B 1.511(13) . ?
C2B H2BA 0.9500 . ?
C11B H11A 0.9800 . ?
C11B H11B 0.9800 . ?
C11B H11C 0.9800 . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C15B N2 1.485(4) . ?
C15B H15A 0.9900 . ?
C15B H15B 0.9900 . ?
C1A C13A 1.523(12) . ?
C1A C15A 1.558(9) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C2A C13A 1.363(12) . ?
C2A C11A 1.526(13) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C15A N2 1.485(4) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
Cl1 Bi1 2.8466(9) 2_666 ?
Cl1 Bi1 2.9877(9) . ?
Cl2 Bi1 2.6593(9) . ?
Cl3 Bi1 2.6536(9) . ?
Cl4 Bi1 2.5281(9) . ?
Cl5 Bi1 2.7028(9) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 113.9(4) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 111.7(3) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 115.0(3) . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
N1 C5 C4 110.9(3) . . ?
N1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C7 121.0(3) . . ?
N1 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C8 120.3(4) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C9 C8 C7 117.2(3) . . ?
C9 C8 C8 122.3(4) . 2_576 ?
C7 C8 C8 120.5(4) . 2_576 ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
N1 C10 C9 120.7(4) . . ?
N1 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
N2 C16 C17 121.1(3) . . ?
N2 C16 H16A 119.4 . . ?
C17 C16 H16A 119.4 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C17 C18 C19 116.8(3) . . ?
C17 C18 C18 120.8(4) . 2_665 ?
C19 C18 C18 122.4(4) . 2_665 ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19A 119.6 . . ?
C18 C19 H19A 119.6 . . ?
N2 C20 C19 120.9(4) . . ?
N2 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C15B C1B C13B 114.4(6) . . ?
C15B C1B H1BA 108.7 . . ?
C13B C1B H1BA 108.7 . . ?
C15B C1B H1BB 108.7 . . ?
C13B C1B H1BB 108.7 . . ?
H1BA C1B H1BB 107.6 . . ?
C13B C2B C11B 131.2(9) . . ?
C13B C2B H2BA 114.4 . . ?
C11B C2B H2BA 114.4 . . ?
C2B C11B H11A 109.5 . . ?
C2B C11B H11B 109.5 . . ?
H11A C11B H11B 109.5 . . ?
C2B C11B H11C 109.5 . . ?
H11A C11B H11C 109.5 . . ?
H11B C11B H11C 109.5 . . ?
C2B C13B C1B 138.9(8) . . ?
C2B C13B H13A 102.4 . . ?
C1B C13B H13A 102.4 . . ?
C2B C13B H13B 102.4 . . ?
C1B C13B H13B 102.4 . . ?
H13A C13B H13B 104.9 . . ?
C1B C15B N2 112.9(4) . . ?
C1B C15B H15A 109.0 . . ?
N2 C15B H15A 109.0 . . ?
C1B C15B H15B 109.0 . . ?
N2 C15B H15B 109.0 . . ?
H15A C15B H15B 107.8 . . ?
C13A C1A C15A 115.4(6) . . ?
C13A C1A H1AA 108.4 . . ?
C15A C1A H1AA 108.4 . . ?
C13A C1A H1AB 108.4 . . ?
C15A C1A H1AB 108.4 . . ?
H1AA C1A H1AB 107.5 . . ?
C13A C2A C11A 116.5(8) . . ?
C13A C2A H2AA 108.2 . . ?
C11A C2A H2AA 108.2 . . ?
C13A C2A H2AB 108.2 . . ?
C11A C2A H2AB 108.2 . . ?
H2AA C2A H2AB 107.3 . . ?
C2A C11A H11D 109.5 . . ?
C2A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C2A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C2A C13A C1A 121.4(8) . . ?
C2A C13A H13C 107.0 . . ?
C1A C13A H13C 107.0 . . ?
C2A C13A H13D 107.0 . . ?
C1A C13A H13D 107.0 . . ?
H13C C13A H13D 106.7 . . ?
N2 C15A C1A 107.4(4) . . ?
N2 C15A H15C 110.2 . . ?
C1A C15A H15C 110.2 . . ?
N2 C15A H15D 110.2 . . ?
C1A C15A H15D 110.2 . . ?
H15C C15A H15D 108.5 . . ?
C6 N1 C10 120.1(3) . . ?
C6 N1 C5 120.4(3) . . ?
C10 N1 C5 119.4(3) . . ?
C20 N2 C16 120.0(3) . . ?
C20 N2 C15A 120.0(3) . . ?
C16 N2 C15A 119.8(3) . . ?
C20 N2 C15B 120.0(3) . . ?
C16 N2 C15B 119.8(3) . . ?
Bi1 Cl1 Bi1 100.49(3) 2_666 . ?
Cl4 Bi1 Cl3 93.09(3) . . ?
Cl4 Bi1 Cl2 91.11(3) . . ?
Cl3 Bi1 Cl2 86.71(3) . . ?
Cl4 Bi1 Cl5 89.79(3) . . ?
Cl3 Bi1 Cl5 86.18(3) . . ?
Cl2 Bi1 Cl5 172.87(3) . . ?
Cl4 Bi1 Cl1 83.57(3) . 2_666 ?
Cl3 Bi1 Cl1 176.03(3) . 2_666 ?
Cl2 Bi1 Cl1 91.20(3) . 2_666 ?
Cl5 Bi1 Cl1 95.94(3) . 2_666 ?
Cl4 Bi1 Cl1 163.02(3) . . ?
Cl3 Bi1 Cl1 103.76(3) . . ?
Cl2 Bi1 Cl1 87.87(3) . . ?
Cl5 Bi1 Cl1 93.32(3) . . ?
Cl1 Bi1 Cl1 79.51(3) 2_666 . ?

_refine_diff_density_max         1.028
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.134


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2003414'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT250_2                   
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.8 Note
RESPONSE: Solution in P1 is unstable, we address the thermal ellipsoids deformation to crystal twinning.
;
_vrf_PLAT971_2                   
;
PROBLEM: Check Calcd Resid. Dens.  0.90A   From Bi1             2.74 eA-3
RESPONSE: Residual densety without any chemical sense
;
_vrf_PLAT972_2                   
;
PROBLEM: Check Calcd Resid. Dens.  0.96A   From Bi1            -2.70 eA-3
RESPONSE: Residual densety without any chemical sense
;
# Added during the CSD deposition process: Tuesday 12 May 2020 07:00 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H52 Bi2 Br10 N4'
_chemical_formula_weight         1757.87

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

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

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

_cell_length_a                   10.4555(3)
_cell_length_b                   11.4437(5)
_cell_length_c                   12.2399(5)
_cell_angle_alpha                75.666(3)
_cell_angle_beta                 67.787(3)
_cell_angle_gamma                65.258(3)
_cell_volume                     1224.38(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4623
_cell_measurement_theta_min      3.8920
_cell_measurement_theta_max      28.7080

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.384
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    15.365
_shelx_estimated_absorpt_T_min   0.091
_shelx_estimated_absorpt_T_max   0.309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38787
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            9188
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.304
_diffrn_reflns_theta_max         29.005
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.801
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.801
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5219
_reflns_number_gt                4730
_reflns_threshold_expression     >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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0432P)²+7.0123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5219
_refine_ls_number_parameters     219
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.021
_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
C2 C 0.2510(10) 0.6036(9) -0.0850(8) 0.0386(10) Uani 1 1 d . U . . .
H2 H 0.336250 0.606461 -0.149890 0.046 Uiso 1 1 calc R U . . .
C3 C 0.0971(9) 0.6558(9) 0.1015(7) 0.0365(10) Uani 1 1 d . U . . .
H3 H 0.072296 0.696269 0.169556 0.044 Uiso 1 1 calc R U . . .
C4 C 0.0090(9) 0.5961(9) 0.0998(7) 0.0368(10) Uani 1 1 d . U . . .
H4 H -0.077125 0.597428 0.165218 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0448(9) 0.5336(9) 0.0032(7) 0.0371(10) Uani 1 1 d . U . . .
C7 C 0.6977(9) 0.0082(7) 0.6266(7) 0.0292(9) Uani 1 1 d . U . . .
H7 H 0.710421 0.063413 0.664980 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5806(10) 0.0552(7) 0.5828(7) 0.0289(9) Uani 1 1 d . U . . .
H8 H 0.513041 0.141850 0.591118 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5610(9) -0.0253(7) 0.5257(7) 0.0269(9) Uani 1 1 d . U . . .
C10 C 0.6624(9) -0.1516(7) 0.5206(7) 0.0266(8) Uani 1 1 d . U . . .
H10 H 0.651934 -0.210112 0.484338 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7759(9) -0.1935(7) 0.5659(7) 0.0268(8) Uani 1 1 d . U . . .
H11 H 0.842889 -0.280764 0.561615 0.032 Uiso 1 1 calc R U . . .
C20 C 0.1671(9) 0.5425(9) -0.0924(8) 0.0389(10) Uani 1 1 d . U . . .
H20 H 0.192447 0.506032 -0.162937 0.047 Uiso 1 1 calc R U . . .
N1 N 0.2159(8) 0.6589(8) 0.0110(6) 0.0362(10) Uani 1 1 d . U . . .
N2 N 0.7945(8) -0.1132(6) 0.6166(6) 0.0277(8) Uani 1 1 d . U . . .
Br1 Br 0.10710(8) 0.78870(7) 0.35398(6) 0.02335(16) Uani 1 1 d . . . . .
Br2 Br 0.34393(7) 0.43872(6) 0.23573(6) 0.01927(15) Uani 1 1 d . . . . .
Br3 Br 0.14796(8) 0.47170(7) 0.58301(6) 0.02381(16) Uani 1 1 d . . . . .
Br4 Br 0.61819(8) 0.33903(7) 0.41154(7) 0.02700(18) Uani 1 1 d . . . . .
Br5 Br 0.52005(9) 0.70770(8) 0.21871(7) 0.03100(19) Uani 1 1 d . . . . .
Bi1 Bi 0.34367(3) 0.57080(2) 0.39623(2) 0.01425(8) Uani 1 1 d . . . . .
C1A C 0.3105(9) 0.7249(8) 0.0153(8) 0.0326(18) Uiso 0.5 1 d . . P A 1
H1A1 H 0.409350 0.691299 -0.043908 0.039 Uiso 0.5 1 calc R U P A 1
H1A2 H 0.324213 0.701611 0.094608 0.039 Uiso 0.5 1 calc R U P A 1
C17 C 0.2467(18) 0.8777(15) -0.0096(14) 0.027(3) Uiso 0.5 1 d . . P A 1
H17A H 0.306019 0.916125 0.006417 0.032 Uiso 0.5 1 calc R U P A 1
H17B H 0.142305 0.913951 0.040505 0.032 Uiso 0.5 1 calc R U P A 1
C19 C 0.259(3) 0.905(2) -0.150(2) 0.056(5) Uiso 0.5 1 d . . P A 1
H19A H 0.187995 0.879260 -0.163856 0.067 Uiso 0.5 1 calc R U P A 1
H19B H 0.360605 0.858107 -0.199048 0.067 Uiso 0.5 1 calc R U P A 1
C23 C 0.218(3) 1.061(2) -0.178(2) 0.067(7) Uiso 0.5 1 d . . P A 1
H23A H 0.170214 1.101041 -0.103486 0.100 Uiso 0.5 1 calc R U P A 1
H23B H 0.150553 1.097371 -0.225920 0.100 Uiso 0.5 1 calc R U P A 1
H23C H 0.309035 1.079684 -0.222159 0.100 Uiso 0.5 1 calc R U P A 1
C1B C 0.3105(9) 0.7249(8) 0.0153(8) 0.0326(18) Uiso 0.5 1 d . . P A 2
H1B1 H 0.273382 0.757830 0.093280 0.039 Uiso 0.5 1 calc R U P A 2
H1B2 H 0.414245 0.663985 0.002483 0.039 Uiso 0.5 1 calc R U P A 2
C18 C 0.303(3) 0.823(3) -0.072(2) 0.070(7) Uiso 0.5 1 d . . P A 2
H18A H 0.360809 0.781124 -0.146010 0.084 Uiso 0.5 1 calc R U P A 2
H18B H 0.361482 0.867846 -0.064211 0.084 Uiso 0.5 1 calc R U P A 2
C22 C 0.171(3) 0.930(2) -0.099(2) 0.059(6) Uiso 0.5 1 d . . P A 2
H22A H 0.101748 0.892251 -0.099856 0.071 Uiso 0.5 1 calc R U P A 2
H22B H 0.118867 0.987582 -0.034980 0.071 Uiso 0.5 1 calc R U P A 2
C24 C 0.206(2) 1.007(2) -0.2102(18) 0.047(5) Uiso 0.5 1 d . . P A 2
H24A H 0.297074 1.020315 -0.222676 0.071 Uiso 0.5 1 calc R U P A 2
H24B H 0.124308 1.090870 -0.209097 0.071 Uiso 0.5 1 calc R U P A 2
H24C H 0.219485 0.962122 -0.274746 0.071 Uiso 0.5 1 calc R U P A 2
C6A C 0.9200(10) -0.1593(8) 0.6667(8) 0.0353(19) Uiso 0.5 1 d . . P B 3
H6A1 H 0.928467 -0.085634 0.688454 0.042 Uiso 0.5 1 calc R U P B 3
H6A2 H 1.014938 -0.204592 0.608355 0.042 Uiso 0.5 1 calc R U P B 3
C13 C 0.8791(15) -0.2578(13) 0.7837(12) 0.019(3) Uiso 0.5 1 d . . P B 3
H13A H 0.876506 -0.331142 0.756485 0.022 Uiso 0.5 1 calc R U P B 3
H13B H 0.962287 -0.293241 0.817058 0.022 Uiso 0.5 1 calc R U P B 3
C21 C 0.7365(19) -0.2096(15) 0.8853(14) 0.025(3) Uiso 0.5 1 d . . P B 3
H21A H 0.650947 -0.176870 0.854973 0.029 Uiso 0.5 1 calc R U P B 3
H21B H 0.727161 -0.283136 0.946513 0.029 Uiso 0.5 1 calc R U P B 3
C15 C 0.7307(19) -0.1042(16) 0.9417(15) 0.035(4) Uiso 0.5 1 d . . P B 3
H15A H 0.828032 -0.124686 0.949292 0.052 Uiso 0.5 1 calc R U P B 3
H15B H 0.656355 -0.097268 1.020498 0.052 Uiso 0.5 1 calc R U P B 3
H15C H 0.703923 -0.021799 0.892049 0.052 Uiso 0.5 1 calc R U P B 3
C6B C 0.9200(10) -0.1593(8) 0.6667(8) 0.0353(19) Uiso 0.5 1 d . . P B 4
H6B1 H 0.964955 -0.254538 0.666936 0.042 Uiso 0.5 1 calc R U P B 4
H6B2 H 0.995681 -0.124387 0.609759 0.042 Uiso 0.5 1 calc R U P B 4
C12 C 0.8970(16) -0.1322(14) 0.7783(13) 0.023(3) Uiso 0.5 1 d . . P B 4
H12A H 0.849285 -0.037576 0.782717 0.028 Uiso 0.5 1 calc R U P B 4
H12B H 0.993273 -0.162199 0.793002 0.028 Uiso 0.5 1 calc R U P B 4
C14 C 0.798(2) -0.2007(17) 0.8727(15) 0.030(4) Uiso 0.5 1 d . . P B 4
H14A H 0.833162 -0.290499 0.853892 0.036 Uiso 0.5 1 calc R U P B 4
H14B H 0.808894 -0.205411 0.950562 0.036 Uiso 0.5 1 calc R U P B 4
C16 C 0.6322(17) -0.1365(15) 0.8842(14) 0.029(3) Uiso 0.5 1 d . . P B 4
H16A H 0.606012 -0.042712 0.865029 0.043 Uiso 0.5 1 calc R U P B 4
H16B H 0.573398 -0.155383 0.965717 0.043 Uiso 0.5 1 calc R U P B 4
H16C H 0.611486 -0.170480 0.829244 0.043 Uiso 0.5 1 calc R U P B 4


_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
C2 N1 1.328(10) . ?
C2 C20 1.368(12) . ?
C2 H2 0.9500 . ?
C3 N1 1.323(11) . ?
C3 C4 1.365(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(11) . ?
C4 H4 0.9500 . ?
C5 C20 1.390(12) . ?
C5 C5 1.471(17) 2_565 ?
C7 N2 1.335(10) . ?
C7 C8 1.371(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(11) . ?
C9 C9 1.471(15) 2_656 ?
C10 C11 1.354(10) . ?
C10 H10 0.9500 . ?
C11 N2 1.338(9) . ?
C11 H11 0.9500 . ?
C20 H20 0.9500 . ?
N1 C1B 1.495(11) . ?
N1 C1A 1.495(11) . ?
N2 C6B 1.499(10) . ?
N2 C6A 1.499(10) . ?
Br1 Bi1 2.7873(7) . ?
Br2 Bi1 2.7580(7) . ?
Br3 Bi1 2.7967(7) . ?
Br4 Bi1 3.0026(7) 2_666 ?
Br4 Bi1 3.0160(8) . ?
Br5 Bi1 2.8773(8) . ?
C1A C17 1.583(17) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C17 C19 1.63(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C23 1.63(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C1B C18 1.34(3) . ?
C1B H1B1 0.9900 . ?
C1B H1B2 0.9900 . ?
C18 C22 1.50(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C22 C24 1.43(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C6A C13 1.627(15) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C13 C21 1.52(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C21 C15 1.50(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C6B C12 1.385(17) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C12 C14 1.54(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C16 1.53(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 C20 121.4(8) . . ?
N1 C2 H2 119.3 . . ?
C20 C2 H2 119.3 . . ?
N1 C3 C4 121.8(7) . . ?
N1 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 120.2(8) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C20 116.7(8) . . ?
C4 C5 C5 122.7(10) . 2_565 ?
C20 C5 C5 120.5(9) . 2_565 ?
N2 C7 C8 121.7(7) . . ?
N2 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C9 119.7(7) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 116.2(7) . . ?
C10 C9 C9 123.5(8) . 2_656 ?
C8 C9 C9 120.2(9) . 2_656 ?
C11 C10 C9 121.8(7) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
N2 C11 C10 120.6(7) . . ?
N2 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C2 C20 C5 120.1(8) . . ?
C2 C20 H20 119.9 . . ?
C5 C20 H20 119.9 . . ?
C3 N1 C2 119.7(8) . . ?
C3 N1 C1B 120.7(7) . . ?
C2 N1 C1B 119.7(7) . . ?
C3 N1 C1A 120.7(7) . . ?
C2 N1 C1A 119.7(7) . . ?
C7 N2 C11 120.0(7) . . ?
C7 N2 C6B 119.2(6) . . ?
C11 N2 C6B 120.7(7) . . ?
C7 N2 C6A 119.2(6) . . ?
C11 N2 C6A 120.7(7) . . ?
Bi1 Br4 Bi1 94.62(2) 2_666 . ?
Br2 Bi1 Br1 92.80(2) . . ?
Br2 Bi1 Br3 92.02(2) . . ?
Br1 Bi1 Br3 90.67(2) . . ?
Br2 Bi1 Br5 94.19(2) . . ?
Br1 Bi1 Br5 83.55(2) . . ?
Br3 Bi1 Br5 171.71(3) . . ?
Br2 Bi1 Br4 168.26(2) . 2_666 ?
Br1 Bi1 Br4 98.52(2) . 2_666 ?
Br3 Bi1 Br4 84.75(2) . 2_666 ?
Br5 Bi1 Br4 90.21(2) . 2_666 ?
Br2 Bi1 Br4 83.66(2) . . ?
Br1 Bi1 Br4 173.35(2) . . ?
Br3 Bi1 Br4 95.07(2) . . ?
Br5 Bi1 Br4 91.07(2) . . ?
Br4 Bi1 Br4 85.38(2) 2_666 . ?
N1 C1A C17 114.9(8) . . ?
N1 C1A H1A1 108.5 . . ?
C17 C1A H1A1 108.5 . . ?
N1 C1A H1A2 108.5 . . ?
C17 C1A H1A2 108.5 . . ?
H1A1 C1A H1A2 107.5 . . ?
C1A C17 C19 104.5(13) . . ?
C1A C17 H17A 110.9 . . ?
C19 C17 H17A 110.9 . . ?
C1A C17 H17B 110.9 . . ?
C19 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C17 C19 C23 103.5(17) . . ?
C17 C19 H19A 111.1 . . ?
C23 C19 H19A 111.1 . . ?
C17 C19 H19B 111.1 . . ?
C23 C19 H19B 111.1 . . ?
H19A C19 H19B 109.0 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C1B N1 106.4(13) . . ?
C18 C1B H1B1 110.5 . . ?
N1 C1B H1B1 110.5 . . ?
C18 C1B H1B2 110.5 . . ?
N1 C1B H1B2 110.5 . . ?
H1B1 C1B H1B2 108.6 . . ?
C1B C18 C22 131(2) . . ?
C1B C18 H18A 104.6 . . ?
C22 C18 H18A 104.6 . . ?
C1B C18 H18B 104.6 . . ?
C22 C18 H18B 104.6 . . ?
H18A C18 H18B 105.7 . . ?
C24 C22 C18 114(2) . . ?
C24 C22 H22A 108.6 . . ?
C18 C22 H22A 108.6 . . ?
C24 C22 H22B 108.6 . . ?
C18 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C6A C13 105.2(7) . . ?
N2 C6A H6A1 110.7 . . ?
C13 C6A H6A1 110.7 . . ?
N2 C6A H6A2 110.7 . . ?
C13 C6A H6A2 110.7 . . ?
H6A1 C6A H6A2 108.8 . . ?
C21 C13 C6A 120.1(11) . . ?
C21 C13 H13A 107.3 . . ?
C6A C13 H13A 107.3 . . ?
C21 C13 H13B 107.3 . . ?
C6A C13 H13B 107.3 . . ?
H13A C13 H13B 106.9 . . ?
C15 C21 C13 113.0(14) . . ?
C15 C21 H21A 109.0 . . ?
C13 C21 H21A 109.0 . . ?
C15 C21 H21B 109.0 . . ?
C13 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C15 H15A 109.5 . . ?
C21 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C21 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C6B N2 121.1(9) . . ?
C12 C6B H6B1 107.0 . . ?
N2 C6B H6B1 107.0 . . ?
C12 C6B H6B2 107.0 . . ?
N2 C6B H6B2 107.0 . . ?
H6B1 C6B H6B2 106.8 . . ?
C6B C12 C14 109.5(12) . . ?
C6B C12 H12A 109.8 . . ?
C14 C12 H12A 109.8 . . ?
C6B C12 H12B 109.8 . . ?
C14 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C16 C14 C12 115.3(13) . . ?
C16 C14 H14A 108.5 . . ?
C12 C14 H14A 108.5 . . ?
C16 C14 H14B 108.5 . . ?
C12 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         2.591
_refine_diff_density_min         -2.741
_refine_diff_density_rms         0.237


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
