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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_a
_database_code_depnum_ccdc_archive 'CCDC 1939021'
loop_
_audit_author_name
_audit_author_address
'Bo Kou'
;Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2019-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Bi3 I14), 2(I3), 6(C8 H22 N2 O)'
_chemical_formula_sum            'C48 H130 Bi6 I34 N12 O6'
_chemical_formula_weight         6540.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   20.1467(13)
_cell_length_b                   22.7942(13)
_cell_length_c                   14.9932(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.472(2)
_cell_angle_gamma                90
_cell_volume                     6883.0(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    15.304
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    3.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             5700
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            89520
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.211
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9825
_reflns_number_total             12087
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         11.227
_refine_diff_density_min         -2.312
_refine_diff_density_rms         0.627
_refine_ls_extinction_coef       0.000068(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         12087
_refine_ls_number_restraints     163
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0877
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+1878.3795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2370
_refine_ls_wR_factor_ref         0.2432
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C17 \\sim N5 \\sim C18: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
C3 \\sim N1 \\sim C2 \\sim C4 \\sim C1: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4.a Ternary CH refined with riding coordinates:
 N1(H1), N6(H6), N2(H2), N3(H3), N4(H4), N5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C20(H20a,H20b), C13(H13a,H13b), C3(H3a,H3b), C14(H14a,H14b),
 C4(H4a,H4b), C5(H5a,H5b), C21(H21a,H21b), C19(H19a,H19b), C22(H22a,H22b),
 C11(H11a,H11b), C12(H12a,H12b)
4.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C1(H1a,H1b,H1c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c),
 C9(H9a,H9b,H9c), C2(H2a,H2b,H2c), C18(H18a,H18b,H18c), C24(H24a,H24b,H24c),
 C17(H17a,H17b,H17c), C10(H10a,H10b,H10c), C7(H7a,H7b,H7c), C23(H23a,H23b,H23c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.26547(6) 0.69846(5) 0.51343(8) 0.0201(3) Uani 1 1 d . U . . .
Bi2 Bi 0.25643(6) 0.51642(5) 0.53071(8) 0.0193(3) Uani 1 1 d . U . . .
Bi3 Bi 0.23839(6) 0.33273(5) 0.22467(8) 0.0209(3) Uani 1 1 d . U . . .
I4 I 0.25473(11) 0.60718(8) 0.68190(13) 0.0214(4) Uani 1 1 d . U . . .
I18 I 0.5000 0.5000 0.0000 0.0251(6) Uani 1 2 d S TU P . .
I5 I 0.15547(10) 0.61137(9) 0.42786(15) 0.0253(5) Uani 1 1 d . U . . .
I15 I 0.0000 0.5000 0.0000 0.0262(7) Uani 1 2 d S TU P . .
I6 I 0.36895(10) 0.59774(9) 0.44912(14) 0.0238(5) Uani 1 1 d . U . . .
I9 I 0.26180(11) 0.44869(9) 0.35518(15) 0.0279(5) Uani 1 1 d . U . . .
I8 I 0.14498(11) 0.44933(9) 0.61062(15) 0.0269(5) Uani 1 1 d . U . . .
I12 I 0.37327(11) 0.28404(9) 0.32517(14) 0.0250(5) Uani 1 1 d . U . . .
I7 I 0.35827(11) 0.44886(9) 0.62704(14) 0.0268(5) Uani 1 1 d . U . . .
I13 I 0.33498(11) 0.39159(10) 0.10612(14) 0.0266(5) Uani 1 1 d . U . . .
I2 I 0.37634(11) 0.76046(9) 0.60793(14) 0.0261(5) Uani 1 1 d . U . . .
I10 I 0.13410(11) 0.39853(10) 0.12373(15) 0.0292(5) Uani 1 1 d . U . . .
I3 I 0.27464(11) 0.76715(10) 0.35235(15) 0.0298(5) Uani 1 1 d . U . . .
I1 I 0.16402(11) 0.77536(10) 0.58994(15) 0.0289(5) Uani 1 1 d . U . . .
I11 I 0.11745(11) 0.29104(10) 0.34387(15) 0.0271(5) Uani 1 1 d . U . . .
I17 I 0.53875(12) 0.59163(10) 0.12847(15) 0.0316(5) Uani 1 1 d . U . . .
I14 I 0.21972(12) 0.23037(10) 0.11251(17) 0.0349(6) Uani 1 1 d . U . . .
I16 I -0.02743(12) 0.40296(11) -0.12233(18) 0.0369(6) Uani 1 1 d . U . . .
O1 O 0.5143(12) 0.3538(10) 0.1754(14) 0.025(5) Uani 1 1 d . U . . .
O3 O -0.0415(11) 0.3515(11) 0.2118(18) 0.034(6) Uani 1 1 d . U . . .
N1 N 0.4710(13) 0.4178(11) 0.3209(17) 0.021(5) Uani 1 1 d . U . . .
H1 H 0.4415 0.3860 0.2964 0.025 Uiso 1 1 calc R . . . .
N6 N 0.0091(15) 0.2440(15) 0.1541(18) 0.032(6) Uani 1 1 d . U . . .
H6 H 0.0380 0.2725 0.1876 0.039 Uiso 1 1 calc R . . . .
N2 N 0.4582(15) 0.2494(12) 0.131(2) 0.033(6) Uani 1 1 d . U . . .
H2 H 0.4412 0.2748 0.1794 0.040 Uiso 1 1 calc R . . . .
N3 N 0.2793(15) 0.5974(14) 0.122(2) 0.034(6) Uani 1 1 d . U . . .
H3 H 0.2708 0.6375 0.0966 0.041 Uiso 1 1 calc R . . . .
O2 O 0.2368(13) 0.5100(9) -0.0262(17) 0.033(5) Uani 1 1 d . U . . .
N4 N 0.2281(14) 0.3926(13) -0.100(2) 0.030(6) Uani 1 1 d . U . . .
H4 H 0.2337 0.3986 -0.0342 0.036 Uiso 1 1 calc R . . . .
C8 C 0.402(2) 0.2126(19) 0.097(3) 0.044(10) Uani 1 1 d . U . . .
H8A H 0.3603 0.2345 0.1016 0.066 Uiso 1 1 calc GR . . . .
H8B H 0.3995 0.1766 0.1326 0.066 Uiso 1 1 calc GR . . . .
H8C H 0.4088 0.2023 0.0343 0.066 Uiso 1 1 calc GR . . . .
C1 C 0.4583(19) 0.4715(14) 0.267(2) 0.031(8) Uani 1 1 d . U . . .
H1A H 0.4943 0.4997 0.2785 0.047 Uiso 1 1 calc GR . . . .
H1B H 0.4161 0.4890 0.2844 0.047 Uiso 1 1 calc GR . . . .
H1C H 0.4562 0.4614 0.2039 0.047 Uiso 1 1 calc GR . . . .
C15 C 0.267(2) 0.3399(17) -0.123(3) 0.045(10) Uani 1 1 d . U . . .
H15A H 0.2627 0.3100 -0.0770 0.068 Uiso 1 1 calc GR . . . .
H15B H 0.3143 0.3508 -0.1277 0.068 Uiso 1 1 calc GR . . . .
H15C H 0.2512 0.3243 -0.1807 0.068 Uiso 1 1 calc GR . . . .
C6 C 0.4835(16) 0.2894(14) 0.059(2) 0.025(6) Uani 1 1 d . U . . .
H6A H 0.4459 0.3123 0.0333 0.029 Uiso 1 1 calc R . . . .
H6B H 0.5018 0.2653 0.0105 0.029 Uiso 1 1 calc R . . . .
N5 N 0.0219(15) 0.4226(14) 0.325(2) 0.034(6) Uani 1 1 d . U . . .
H5 H 0.0463 0.3873 0.3037 0.041 Uiso 1 1 calc R . . . .
C20 C -0.0708(17) 0.4055(15) 0.220(3) 0.031(7) Uani 1 1 d . U . . .
H20A H -0.1064 0.4036 0.2639 0.038 Uiso 1 1 calc R . . . .
H20B H -0.0908 0.4176 0.1616 0.038 Uiso 1 1 calc R . . . .
C13 C 0.223(2) 0.4989(16) -0.114(3) 0.038(8) Uani 1 1 d . U . . .
H13A H 0.2369 0.5330 -0.1505 0.045 Uiso 1 1 calc R . . . .
H13B H 0.1750 0.4932 -0.1239 0.045 Uiso 1 1 calc R . . . .
C16 C 0.1569(19) 0.3830(19) -0.119(3) 0.046(10) Uani 1 1 d . U . . .
H16A H 0.1496 0.3765 -0.1832 0.069 Uiso 1 1 calc GR . . . .
H16B H 0.1318 0.4175 -0.1006 0.069 Uiso 1 1 calc GR . . . .
H16C H 0.1419 0.3485 -0.0861 0.069 Uiso 1 1 calc GR . . . .
C9 C 0.293(3) 0.6036(17) 0.221(3) 0.047(10) Uani 1 1 d . U . . .
H9A H 0.3232 0.5721 0.2412 0.071 Uiso 1 1 calc GR . . . .
H9B H 0.2515 0.6010 0.2529 0.071 Uiso 1 1 calc GR . . . .
H9C H 0.3142 0.6416 0.2332 0.071 Uiso 1 1 calc GR . . . .
C3 C 0.5438(16) 0.3987(14) 0.309(2) 0.023(5) Uani 1 1 d . U . . .
H3A H 0.5734 0.4288 0.3356 0.027 Uiso 1 1 calc R . . . .
H3B H 0.5516 0.3616 0.3416 0.027 Uiso 1 1 calc R . . . .
C2 C 0.4585(18) 0.4236(19) 0.413(2) 0.035(8) Uani 1 1 d . U . . .
H2A H 0.4858 0.4555 0.4379 0.053 Uiso 1 1 calc GR . . . .
H2B H 0.4696 0.3868 0.4435 0.053 Uiso 1 1 calc GR . . . .
H2C H 0.4114 0.4326 0.4206 0.053 Uiso 1 1 calc GR . . . .
C14 C 0.2596(19) 0.4449(15) -0.145(3) 0.034(8) Uani 1 1 d . U . . .
H14A H 0.3073 0.4475 -0.1284 0.040 Uiso 1 1 calc R . . . .
H14B H 0.2553 0.4410 -0.2109 0.040 Uiso 1 1 calc R . . . .
C4 C 0.5626(18) 0.3899(18) 0.216(2) 0.032(7) Uani 1 1 d . U . . .
H4A H 0.5645 0.4280 0.1844 0.038 Uiso 1 1 calc R . . . .
H4B H 0.6068 0.3710 0.2135 0.038 Uiso 1 1 calc R . . . .
C18 C -0.022(2) 0.4057(17) 0.401(3) 0.044(10) Uani 1 1 d . U . . .
H18A H -0.0338 0.4409 0.4341 0.066 Uiso 1 1 calc GR . . . .
H18B H 0.0023 0.3784 0.4406 0.066 Uiso 1 1 calc GR . . . .
H18C H -0.0620 0.3867 0.3768 0.066 Uiso 1 1 calc GR . . . .
C5 C 0.5365(19) 0.3312(17) 0.093(2) 0.032(8) Uani 1 1 d . U . . .
H5A H 0.5793 0.3104 0.1024 0.039 Uiso 1 1 calc R . . . .
H5B H 0.5430 0.3635 0.0502 0.039 Uiso 1 1 calc R . . . .
C21 C -0.089(2) 0.3030(18) 0.181(3) 0.045(10) Uani 1 1 d . U . . .
H21A H -0.1291 0.3033 0.2177 0.054 Uiso 1 1 calc R . . . .
H21B H -0.1024 0.3089 0.1180 0.054 Uiso 1 1 calc R . . . .
C19 C -0.0191(19) 0.4491(15) 0.249(2) 0.032(6) Uani 1 1 d . U . . .
H19A H -0.0407 0.4856 0.2696 0.038 Uiso 1 1 calc R . . . .
H19B H 0.0098 0.4589 0.1992 0.038 Uiso 1 1 calc R . . . .
C24 C 0.011(2) 0.2620(19) 0.056(2) 0.047(11) Uani 1 1 d . U . . .
H24A H -0.0236 0.2403 0.0222 0.071 Uiso 1 1 calc GR . . . .
H24B H 0.0543 0.2531 0.0325 0.071 Uiso 1 1 calc GR . . . .
H24C H 0.0020 0.3042 0.0508 0.071 Uiso 1 1 calc GR . . . .
C17 C 0.0731(19) 0.4724(17) 0.354(3) 0.045(9) Uani 1 1 d . U . . .
H17A H 0.0492 0.5055 0.3793 0.067 Uiso 1 1 calc GR . . . .
H17B H 0.0969 0.4856 0.3010 0.067 Uiso 1 1 calc GR . . . .
H17C H 0.1050 0.4568 0.3980 0.067 Uiso 1 1 calc GR . . . .
C10 C 0.3395(18) 0.5743(19) 0.082(3) 0.048(11) Uani 1 1 d . U . . .
H10A H 0.3757 0.6027 0.0901 0.072 Uiso 1 1 calc GR . . . .
H10B H 0.3313 0.5676 0.0180 0.072 Uiso 1 1 calc GR . . . .
H10C H 0.3518 0.5372 0.1109 0.072 Uiso 1 1 calc GR . . . .
C22 C -0.0536(19) 0.2469(16) 0.192(3) 0.036(7) Uani 1 1 d . U . . .
H22A H -0.0483 0.2386 0.2567 0.043 Uiso 1 1 calc R . . . .
H22B H -0.0817 0.2155 0.1656 0.043 Uiso 1 1 calc R . . . .
C7 C 0.510(2) 0.215(3) 0.167(3) 0.068(16) Uani 1 1 d . U . . .
H7A H 0.4938 0.1934 0.2184 0.102 Uiso 1 1 calc GR . . . .
H7B H 0.5467 0.2406 0.1861 0.102 Uiso 1 1 calc GR . . . .
H7C H 0.5251 0.1875 0.1218 0.102 Uiso 1 1 calc GR . . . .
C11 C 0.220(2) 0.563(2) 0.107(3) 0.045(9) Uani 1 1 d . U . . .
H11A H 0.1829 0.5812 0.1381 0.054 Uiso 1 1 calc R . . . .
H11B H 0.2274 0.5232 0.1331 0.054 Uiso 1 1 calc R . . . .
C23 C 0.038(2) 0.187(2) 0.168(3) 0.056(12) Uani 1 1 d . U . . .
H23A H 0.0161 0.1585 0.1282 0.084 Uiso 1 1 calc GR . . . .
H23B H 0.0327 0.1750 0.2301 0.084 Uiso 1 1 calc GR . . . .
H23C H 0.0856 0.1886 0.1550 0.084 Uiso 1 1 calc GR . . . .
C12 C 0.2016(16) 0.5562(18) 0.010(3) 0.035(8) Uani 1 1 d . U . . .
H12A H 0.1533 0.5486 0.0031 0.042 Uiso 1 1 calc R . . . .
H12B H 0.2118 0.5929 -0.0221 0.042 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I4 3.284(2) . ?
Bi1 I5 3.218(2) . ?
Bi1 I6 3.263(2) . ?
Bi1 I2 2.972(2) . ?
Bi1 I3 2.888(2) . ?
Bi1 I1 2.947(2) . ?
Bi2 I4 3.070(2) . ?
Bi2 I5 3.322(2) . ?
Bi2 I6 3.196(2) . ?
Bi2 I9 3.055(2) . ?
Bi2 I8 2.992(2) . ?
Bi2 I7 2.918(2) . ?
Bi3 I9 3.315(2) . ?
Bi3 I12 3.267(2) . ?
Bi3 I13 2.987(2) . ?
Bi3 I10 2.965(2) . ?
Bi3 I11 3.203(2) . ?
Bi3 I14 2.895(3) . ?
I18 I17 2.933(2) . ?
I18 I17 2.933(2) 3_665 ?
I15 I16 2.917(2) 3_565 ?
I15 I16 2.917(2) . ?
O1 C4 1.40(4) . ?
O1 C5 1.42(4) . ?
O3 C20 1.37(4) . ?
O3 C21 1.52(4) . ?
N1 C1 1.48(4) . ?
N1 C3 1.55(4) . ?
N1 C2 1.41(4) . ?
N6 C24 1.53(4) . ?
N6 C22 1.40(5) . ?
N6 C23 1.44(5) . ?
N2 C8 1.49(4) . ?
N2 C6 1.51(4) . ?
N2 C7 1.40(5) . ?
N3 C9 1.52(5) . ?
N3 C10 1.46(5) . ?
N3 C11 1.44(5) . ?
O2 C13 1.37(5) . ?
O2 C12 1.39(4) . ?
N4 C15 1.49(5) . ?
N4 C16 1.47(5) . ?
N4 C14 1.52(4) . ?
C6 C5 1.51(5) . ?
N5 C18 1.50(5) . ?
N5 C19 1.52(5) . ?
N5 C17 1.58(5) . ?
C20 C19 1.50(5) . ?
C13 C14 1.51(5) . ?
C3 C4 1.46(4) . ?
C21 C22 1.47(6) . ?
C11 C12 1.50(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I5 Bi1 I4 81.80(6) . . ?
I5 Bi1 I6 83.50(6) . . ?
I6 Bi1 I4 80.60(6) . . ?
I2 Bi1 I4 89.90(6) . . ?
I2 Bi1 I5 170.10(7) . . ?
I2 Bi1 I6 89.85(6) . . ?
I3 Bi1 I4 173.49(7) . . ?
I3 Bi1 I5 93.40(7) . . ?
I3 Bi1 I6 94.54(7) . . ?
I3 Bi1 I2 94.44(7) . . ?
I3 Bi1 I1 93.61(7) . . ?
I1 Bi1 I4 91.00(7) . . ?
I1 Bi1 I5 92.56(7) . . ?
I1 Bi1 I6 171.14(7) . . ?
I1 Bi1 I2 92.97(7) . . ?
I4 Bi2 I5 83.42(6) . . ?
I4 Bi2 I6 85.02(6) . . ?
I6 Bi2 I5 82.90(6) . . ?
I9 Bi2 I4 167.92(7) . . ?
I9 Bi2 I5 87.95(6) . . ?
I9 Bi2 I6 85.54(6) . . ?
I8 Bi2 I4 91.49(6) . . ?
I8 Bi2 I5 93.56(7) . . ?
I8 Bi2 I6 175.28(7) . . ?
I8 Bi2 I9 97.48(7) . . ?
I7 Bi2 I4 90.64(7) . . ?
I7 Bi2 I5 171.04(7) . . ?
I7 Bi2 I6 89.94(7) . . ?
I7 Bi2 I9 96.87(7) . . ?
I7 Bi2 I8 93.29(7) . . ?
I12 Bi3 I9 83.95(6) . . ?
I13 Bi3 I9 84.73(6) . . ?
I13 Bi3 I12 83.12(6) . . ?
I13 Bi3 I11 169.06(7) . . ?
I10 Bi3 I9 89.21(7) . . ?
I10 Bi3 I12 167.76(7) . . ?
I10 Bi3 I13 86.16(7) . . ?
I10 Bi3 I11 84.01(7) . . ?
I11 Bi3 I9 90.34(6) . . ?
I11 Bi3 I12 106.11(6) . . ?
I14 Bi3 I9 178.99(8) . . ?
I14 Bi3 I12 95.06(7) . . ?
I14 Bi3 I13 95.35(7) . . ?
I14 Bi3 I10 91.80(8) . . ?
I14 Bi3 I11 89.75(7) . . ?
Bi2 I4 Bi1 81.77(5) . . ?
I17 I18 I17 180.0 3_665 . ?
Bi1 I5 Bi2 79.03(5) . . ?
I16 I15 I16 180.0 3_565 . ?
Bi2 I6 Bi1 80.22(6) . . ?
Bi2 I9 Bi3 154.63(9) . . ?
C4 O1 C5 111(3) . . ?
C20 O3 C21 114(3) . . ?
C1 N1 C3 109(2) . . ?
C2 N1 C1 115(3) . . ?
C2 N1 C3 110(2) . . ?
C22 N6 C24 115(3) . . ?
C22 N6 C23 111(3) . . ?
C23 N6 C24 111(3) . . ?
C8 N2 C6 112(3) . . ?
C7 N2 C8 112(4) . . ?
C7 N2 C6 111(3) . . ?
C10 N3 C9 107(3) . . ?
C11 N3 C9 109(3) . . ?
C11 N3 C10 115(3) . . ?
C13 O2 C12 115(3) . . ?
C15 N4 C14 107(3) . . ?
C16 N4 C15 111(3) . . ?
C16 N4 C14 117(3) . . ?
N2 C6 C5 113(3) . . ?
C18 N5 C19 111(3) . . ?
C18 N5 C17 112(3) . . ?
C19 N5 C17 105(3) . . ?
O3 C20 C19 109(3) . . ?
O2 C13 C14 111(3) . . ?
C4 C3 N1 115(3) . . ?
C13 C14 N4 107(3) . . ?
O1 C4 C3 107(3) . . ?
O1 C5 C6 107(3) . . ?
C22 C21 O3 108(3) . . ?
C20 C19 N5 109(3) . . ?
N6 C22 C21 116(3) . . ?
N3 C11 C12 113(3) . . ?
O2 C12 C11 110(3) . . ?

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

data_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1939023'
loop_
_audit_author_name
_audit_author_address
'Bo Kou'
;Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2019-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I8, C8 H22 N2 O'
_chemical_formula_sum            'C8 H22 Bi2 I8 N2 O'
_chemical_formula_weight         1595.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.4885(7)
_cell_length_b                   24.8912(17)
_cell_length_c                   12.3295(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.343(2)
_cell_angle_gamma                90
_cell_volume                     2955.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5332
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.51
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.250
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2728
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1221
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33809
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3404
_reflns_number_total             5204
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.556
_refine_diff_density_min         -1.680
_refine_diff_density_rms         0.344
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         5204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1134
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C3(H3A,H3B), C6(H6A,H6B), C4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.43753(6) 0.41235(3) 0.42329(6) 0.03814(19) Uani 1 1 d . . . . .
Bi2 Bi 0.83994(6) 0.36979(3) 0.69241(6) 0.0421(2) Uani 1 1 d . . . . .
I5 I 0.63788(11) 0.33045(5) 0.40411(10) 0.0468(3) Uani 1 1 d . . . . .
I8 I 0.26844(11) 0.51187(5) 0.45846(10) 0.0476(3) Uani 1 1 d . . . . .
I6 I 0.38647(12) 0.44564(5) 0.17105(10) 0.0512(3) Uani 1 1 d . . . . .
I4 I 0.51350(12) 0.37906(5) 0.68554(10) 0.0527(3) Uani 1 1 d . . . . .
I7 I 0.20075(12) 0.34121(5) 0.34514(11) 0.0541(3) Uani 1 1 d . . . . .
I3 I 0.98257(13) 0.43205(6) 0.90312(11) 0.0623(4) Uani 1 1 d . . . . .
I1 I 1.06676(13) 0.36117(6) 0.61625(12) 0.0652(4) Uani 1 1 d . . . . .
I2 I 0.88626(14) 0.26853(6) 0.81652(14) 0.0746(4) Uani 1 1 d . . . . .
O1 O 0.6344(12) 0.3587(5) 0.0712(11) 0.056(3) Uani 1 1 d . . . . .
N2 N 0.3864(14) 0.3122(6) 0.0494(12) 0.050(4) Uani 1 1 d . . . . .
H2 H 0.420101 0.345236 0.094979 0.060 Uiso 1 1 calc R . . . .
N1 N 0.7497(15) 0.4527(6) 0.2020(13) 0.055(4) Uani 1 1 d . . . . .
H1 H 0.670490 0.434702 0.209465 0.066 Uiso 1 1 calc R . . . .
C5 C 0.6117(18) 0.3047(7) 0.0259(17) 0.055(5) Uani 1 1 d . . . . .
H5A H 0.698674 0.285039 0.055455 0.066 Uiso 1 1 calc R . . . .
H5B H 0.576441 0.305350 -0.059628 0.066 Uiso 1 1 calc R . . . .
C7 C 0.307(2) 0.3263(8) -0.0780(17) 0.069(6) Uani 1 1 d . . . . .
H7A H 0.367028 0.344964 -0.107242 0.104 Uiso 1 1 calc GR . . . .
H7B H 0.229949 0.348928 -0.085334 0.104 Uiso 1 1 calc GR . . . .
H7C H 0.273433 0.294034 -0.122945 0.104 Uiso 1 1 calc GR . . . .
C3 C 0.741(2) 0.4416(8) 0.0813(18) 0.076(7) Uani 1 1 d . . . . .
H3A H 0.820551 0.458024 0.072357 0.092 Uiso 1 1 calc R . . . .
H3B H 0.658111 0.458264 0.024498 0.092 Uiso 1 1 calc R . . . .
C2 C 0.736(2) 0.5109(8) 0.221(2) 0.089(8) Uani 1 1 d . . . . .
H2A H 0.746910 0.516798 0.301193 0.134 Uiso 1 1 calc GR . . . .
H2B H 0.646291 0.523183 0.168159 0.134 Uiso 1 1 calc GR . . . .
H2C H 0.806736 0.530341 0.206312 0.134 Uiso 1 1 calc GR . . . .
C1 C 0.878(2) 0.4312(10) 0.2978(19) 0.094(8) Uani 1 1 d . . . . .
H1A H 0.950097 0.427710 0.268743 0.141 Uiso 1 1 calc GR . . . .
H1B H 0.858692 0.396708 0.322507 0.141 Uiso 1 1 calc GR . . . .
H1C H 0.907862 0.455492 0.363745 0.141 Uiso 1 1 calc GR . . . .
C6 C 0.5069(17) 0.2767(7) 0.0650(17) 0.058(5) Uani 1 1 d . . . . .
H6A H 0.473892 0.244188 0.019129 0.069 Uiso 1 1 calc R . . . .
H6B H 0.552565 0.266584 0.147504 0.069 Uiso 1 1 calc R . . . .
C4 C 0.739(2) 0.3830(9) 0.0538(19) 0.073(6) Uani 1 1 d . . . . .
H4A H 0.727285 0.378312 -0.027751 0.088 Uiso 1 1 calc R . . . .
H4B H 0.826513 0.366688 0.104064 0.088 Uiso 1 1 calc R . . . .
C8 C 0.290(2) 0.2841(9) 0.093(2) 0.099(9) Uani 1 1 d . . . . .
H8A H 0.215697 0.307995 0.088295 0.149 Uiso 1 1 calc GR . . . .
H8B H 0.339598 0.273400 0.173917 0.149 Uiso 1 1 calc GR . . . .
H8C H 0.251632 0.252888 0.045619 0.149 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I5 3.0035(13) . ?
Bi1 I8 3.1747(13) . ?
Bi1 I8 3.4104(13) 3_666 ?
Bi1 I6 3.0538(13) . ?
Bi1 I4 3.1200(13) . ?
Bi1 I7 2.8871(13) . ?
Bi2 I5 3.4807(13) . ?
Bi2 I8 3.4281(14) 3_666 ?
Bi2 I4 3.3990(13) . ?
Bi2 I3 2.8824(14) . ?
Bi2 I1 2.8910(14) . ?
Bi2 I2 2.8883(15) . ?
O1 C5 1.438(18) . ?
O1 C4 1.34(2) . ?
N2 H2 0.9800 . ?
N2 C7 1.50(2) . ?
N2 C6 1.49(2) . ?
N2 C8 1.50(2) . ?
N1 H1 0.9800 . ?
N1 C3 1.48(2) . ?
N1 C2 1.48(2) . ?
N1 C1 1.49(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.53(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.50(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I5 Bi1 I8 170.56(4) . . ?
I5 Bi1 I8 82.34(3) . 3_666 ?
I5 Bi1 I6 87.12(4) . . ?
I5 Bi1 I4 90.11(4) . . ?
I8 Bi1 I8 88.26(3) . 3_666 ?
I6 Bi1 I8 92.82(3) . 3_666 ?
I6 Bi1 I8 92.60(4) . . ?
I6 Bi1 I4 175.70(4) . . ?
I4 Bi1 I8 89.59(4) . . ?
I4 Bi1 I8 83.54(3) . 3_666 ?
I7 Bi1 I5 95.37(4) . . ?
I7 Bi1 I8 94.07(4) . . ?
I7 Bi1 I8 173.96(4) . 3_666 ?
I7 Bi1 I6 92.64(4) . . ?
I7 Bi1 I4 90.90(4) . . ?
I8 Bi2 I5 75.57(3) 3_666 . ?
I4 Bi2 I5 78.11(3) . . ?
I4 Bi2 I8 79.28(3) . 3_666 ?
I3 Bi2 I5 163.78(4) . . ?
I3 Bi2 I8 88.24(4) . 3_666 ?
I3 Bi2 I4 98.27(4) . . ?
I3 Bi2 I1 97.62(4) . . ?
I3 Bi2 I2 94.21(5) . . ?
I1 Bi2 I5 83.91(4) . . ?
I1 Bi2 I8 91.50(4) . 3_666 ?
I1 Bi2 I4 161.33(4) . . ?
I2 Bi2 I5 101.66(4) . . ?
I2 Bi2 I8 170.86(4) . 3_666 ?
I2 Bi2 I4 91.65(4) . . ?
I2 Bi2 I1 96.89(5) . . ?
Bi1 I5 Bi2 83.71(3) . . ?
Bi1 I8 Bi1 91.74(3) . 3_666 ?
Bi1 I8 Bi2 78.82(3) 3_666 3_666 ?
Bi1 I8 Bi2 132.79(4) . 3_666 ?
Bi1 I4 Bi2 83.39(3) . . ?
C4 O1 C5 112.3(14) . . ?
C7 N2 H2 109.1 . . ?
C6 N2 H2 109.1 . . ?
C6 N2 C7 111.3(13) . . ?
C6 N2 C8 109.8(15) . . ?
C8 N2 H2 109.1 . . ?
C8 N2 C7 108.3(15) . . ?
C3 N1 H1 107.1 . . ?
C3 N1 C2 111.7(15) . . ?
C3 N1 C1 113.8(16) . . ?
C2 N1 H1 107.1 . . ?
C2 N1 C1 109.7(17) . . ?
C1 N1 H1 107.1 . . ?
O1 C5 H5A 109.8 . . ?
O1 C5 H5B 109.8 . . ?
O1 C5 C6 109.4(14) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
N1 C3 C4 113.5(16) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C6 C5 111.6(15) . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
O1 C4 C3 110.2(16) . . ?
O1 C4 H4A 109.6 . . ?
O1 C4 H4B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 N2 45(2) . . . . ?
N1 C3 C4 O1 56(3) . . . . ?
C5 O1 C4 C3 169.5(16) . . . . ?
C7 N2 C6 C5 62.4(19) . . . . ?
C2 N1 C3 C4 -173.7(18) . . . . ?
C1 N1 C3 C4 61(2) . . . . ?
C4 O1 C5 C6 171.5(16) . . . . ?
C8 N2 C6 C5 -177.7(15) . . . . ?

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

data_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1939022'
loop_
_audit_author_name
_audit_author_address
'Bo Kou'
;Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2019-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, 2(C8 H22 N2 O), I'
_chemical_formula_sum            'C16 H44 Bi2 I10 N4 O2'
_chemical_formula_weight         2011.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.7709(7)
_cell_length_b                   22.3276(12)
_cell_length_c                   24.5774(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8654.3(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5332
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.51
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    15.276
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.088
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             7040
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            69514
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8967
_reflns_number_total             9885
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.846
_refine_diff_density_min         -2.488
_refine_diff_density_rms         0.245
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         9885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+38.3674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0693
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N4(H4), N3(H3), N2(H2), N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C6(H6a,H6b), C4(H4a,H4b), C11(H11a,H11b), C12(H12a,H12b),
 C14(H14a,H14b), C3(H3a,H3b), C5(H5a,H5b)
2.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C2(H2a,H2b,H2c), C10(H10a,H10b,H10c), C7(H7a,H7b,H7c),
 C8(H8a,H8b,H8c), C1(H1a,H1b,H1c), C9(H9a,H9b,H9c), C15(H15a,H15b,H15c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.52089(2) 0.47822(2) 0.84302(2) 0.01195(5) Uani 1 1 d . . . . .
Bi2 Bi 0.54214(2) 0.28738(2) 0.84935(2) 0.01113(5) Uani 1 1 d . . . . .
I6 I 0.48324(2) 0.36551(2) 0.74894(2) 0.01320(8) Uani 1 1 d . . . . .
I5 I 0.43102(2) 0.37626(2) 0.92215(2) 0.01394(8) Uani 1 1 d . . . . .
I2 I 0.55713(2) 0.55017(2) 0.93730(2) 0.01400(8) Uani 1 1 d . . . . .
I4 I 0.68747(2) 0.39622(2) 0.86273(2) 0.01566(8) Uani 1 1 d . . . . .
I9 I 0.64793(2) 0.20996(2) 0.77815(2) 0.01890(9) Uani 1 1 d . . . . .
I1 I 0.35548(2) 0.53899(2) 0.82626(2) 0.01640(8) Uani 1 1 d . . . . .
I7 I 0.39904(2) 0.20509(2) 0.83537(2) 0.01790(9) Uani 1 1 d . . . . .
I3 I 0.61079(3) 0.55925(2) 0.76934(2) 0.02126(9) Uani 1 1 d . . . . .
I8 I 0.60803(3) 0.23178(2) 0.95228(2) 0.02194(9) Uani 1 1 d . . . . .
O2 O 0.5949(3) 0.26685(19) 0.63031(18) 0.0183(9) Uani 1 1 d . . . . .
N4 N 0.4259(3) 0.2464(2) 0.6247(2) 0.0212(12) Uani 1 1 d . . . . .
H4 H 0.452865 0.286915 0.625230 0.025 Uiso 1 1 calc R . . . .
N3 N 0.6796(3) 0.3651(2) 0.6721(2) 0.0163(11) Uani 1 1 d . . . . .
H3 H 0.629210 0.344005 0.687749 0.020 Uiso 1 1 calc R . . . .
O1 O 0.3001(3) 0.51412(19) 0.52327(17) 0.0157(9) Uani 1 1 d . . . . .
N2 N 0.3805(3) 0.5364(2) 0.6213(2) 0.0146(10) Uani 1 1 d . . . . .
H2 H 0.380431 0.497524 0.601067 0.018 Uiso 1 1 calc R . . . .
N1 N 0.2613(3) 0.4022(2) 0.4882(2) 0.0155(10) Uani 1 1 d . . . . .
H1 H 0.278313 0.409974 0.526767 0.019 Uiso 1 1 calc R . . . .
C16 C 0.4119(5) 0.2290(3) 0.5666(3) 0.0302(16) Uani 1 1 d . . . . .
H16A H 0.464552 0.234507 0.546042 0.045 Uiso 1 1 calc GR . . . .
H16B H 0.367236 0.254115 0.550836 0.045 Uiso 1 1 calc GR . . . .
H16C H 0.394635 0.186830 0.564779 0.045 Uiso 1 1 calc GR . . . .
C2 C 0.1676(4) 0.4117(3) 0.4839(3) 0.0216(14) Uani 1 1 d . . . . .
H2A H 0.152880 0.450731 0.499439 0.032 Uiso 1 1 calc GR . . . .
H2B H 0.137966 0.380000 0.503833 0.032 Uiso 1 1 calc GR . . . .
H2C H 0.150754 0.410580 0.445518 0.032 Uiso 1 1 calc GR . . . .
C13 C 0.5714(4) 0.2058(3) 0.6286(3) 0.0225(14) Uani 1 1 d . . . . .
H13A H 0.611629 0.181178 0.650020 0.027 Uiso 1 1 calc R . . . .
H13B H 0.570654 0.190982 0.590692 0.027 Uiso 1 1 calc R . . . .
C10 C 0.7553(4) 0.3492(3) 0.7065(3) 0.0236(14) Uani 1 1 d . . . . .
H10A H 0.767052 0.306256 0.703224 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.743510 0.359014 0.744632 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.804743 0.372037 0.694075 0.035 Uiso 1 1 calc GR . . . .
C7 C 0.4619(4) 0.5674(3) 0.6089(3) 0.0234(15) Uani 1 1 d . . . . .
H7A H 0.465318 0.575550 0.569810 0.035 Uiso 1 1 calc GR . . . .
H7B H 0.509520 0.541857 0.619794 0.035 Uiso 1 1 calc GR . . . .
H7C H 0.464479 0.605270 0.629060 0.035 Uiso 1 1 calc GR . . . .
C6 C 0.3053(4) 0.5713(3) 0.6030(3) 0.0176(13) Uani 1 1 d . . . . .
H6A H 0.308910 0.612487 0.617722 0.021 Uiso 1 1 calc R . . . .
H6B H 0.253180 0.552551 0.617632 0.021 Uiso 1 1 calc R . . . .
C4 C 0.2944(4) 0.5086(3) 0.4658(3) 0.0188(13) Uani 1 1 d . . . . .
H4A H 0.336822 0.534624 0.447892 0.023 Uiso 1 1 calc R . . . .
H4B H 0.237233 0.520308 0.453100 0.023 Uiso 1 1 calc R . . . .
C8 C 0.3747(4) 0.5223(3) 0.6805(3) 0.0249(15) Uani 1 1 d . . . . .
H8A H 0.424552 0.499145 0.691544 0.037 Uiso 1 1 calc GR . . . .
H8B H 0.323284 0.498898 0.687406 0.037 Uiso 1 1 calc GR . . . .
H8C H 0.372447 0.559702 0.701310 0.037 Uiso 1 1 calc GR . . . .
C11 C 0.6891(4) 0.3450(3) 0.6145(2) 0.0203(14) Uani 1 1 d . . . . .
H11A H 0.746169 0.356087 0.601046 0.024 Uiso 1 1 calc R . . . .
H11B H 0.646604 0.365737 0.591522 0.024 Uiso 1 1 calc R . . . .
C12 C 0.6773(4) 0.2784(3) 0.6096(3) 0.0212(14) Uani 1 1 d . . . . .
H12A H 0.681585 0.265646 0.571116 0.025 Uiso 1 1 calc R . . . .
H12B H 0.720693 0.256870 0.631088 0.025 Uiso 1 1 calc R . . . .
C14 C 0.4845(5) 0.2033(3) 0.6530(3) 0.0248(15) Uani 1 1 d . . . . .
H14A H 0.487672 0.213544 0.692185 0.030 Uiso 1 1 calc R . . . .
H14B H 0.461749 0.162154 0.649811 0.030 Uiso 1 1 calc R . . . .
C3 C 0.3115(4) 0.4434(3) 0.4525(3) 0.0174(13) Uani 1 1 d . . . . .
H3A H 0.296690 0.435758 0.413947 0.021 Uiso 1 1 calc R . . . .
H3B H 0.372705 0.434981 0.457138 0.021 Uiso 1 1 calc R . . . .
C1 C 0.2831(4) 0.3388(3) 0.4752(3) 0.0230(14) Uani 1 1 d . . . . .
H1A H 0.251532 0.311958 0.499420 0.035 Uiso 1 1 calc GR . . . .
H1B H 0.344076 0.332545 0.480351 0.035 Uiso 1 1 calc GR . . . .
H1C H 0.267966 0.330196 0.437339 0.035 Uiso 1 1 calc GR . . . .
C5 C 0.2994(4) 0.5741(3) 0.5418(3) 0.0167(12) Uani 1 1 d . . . . .
H5A H 0.246379 0.594419 0.530594 0.020 Uiso 1 1 calc R . . . .
H5B H 0.348139 0.596516 0.526639 0.020 Uiso 1 1 calc R . . . .
C9 C 0.6625(5) 0.4305(3) 0.6744(4) 0.0316(17) Uani 1 1 d . . . . .
H9A H 0.658126 0.443214 0.712466 0.047 Uiso 1 1 calc GR . . . .
H9B H 0.609184 0.439267 0.655538 0.047 Uiso 1 1 calc GR . . . .
H9C H 0.708976 0.452200 0.656712 0.047 Uiso 1 1 calc GR . . . .
C15 C 0.3442(5) 0.2501(4) 0.6552(4) 0.044(2) Uani 1 1 d . . . . .
H15A H 0.306853 0.279277 0.637461 0.066 Uiso 1 1 calc GR . . . .
H15B H 0.355382 0.262838 0.692661 0.066 Uiso 1 1 calc GR . . . .
H15C H 0.316832 0.210740 0.655407 0.066 Uiso 1 1 calc GR . . . .
I10 I 0.45810(2) 0.39853(2) 0.57163(2) 0.01873(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I6 3.4688(5) . ?
Bi1 I5 3.3126(5) . ?
Bi1 I2 2.8769(4) . ?
Bi1 I4 3.2387(4) . ?
Bi1 I1 2.9690(4) . ?
Bi1 I3 2.9262(5) . ?
Bi2 I6 3.1617(4) . ?
Bi2 I5 3.1954(4) . ?
Bi2 I4 3.3565(5) . ?
Bi2 I9 2.9721(5) . ?
Bi2 I7 2.9303(5) . ?
Bi2 I8 3.0035(5) . ?
O2 C13 1.412(8) . ?
O2 C12 1.420(7) . ?
N4 H4 1.0000 . ?
N4 C16 1.497(9) . ?
N4 C14 1.505(9) . ?
N4 C15 1.492(9) . ?
N3 H3 1.0000 . ?
N3 C10 1.506(8) . ?
N3 C11 1.493(8) . ?
N3 C9 1.487(9) . ?
O1 C4 1.420(7) . ?
O1 C5 1.416(7) . ?
N2 H2 1.0000 . ?
N2 C7 1.491(7) . ?
N2 C6 1.490(8) . ?
N2 C8 1.490(8) . ?
N1 H1 1.0000 . ?
N1 C2 1.497(8) . ?
N1 C3 1.498(8) . ?
N1 C1 1.491(8) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.498(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.507(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.515(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.503(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
I5 Bi1 I6 79.602(11) . . ?
I2 Bi1 I6 167.424(13) . . ?
I2 Bi1 I5 89.763(12) . . ?
I2 Bi1 I4 91.951(12) . . ?
I2 Bi1 I1 91.785(13) . . ?
I2 Bi1 I3 93.268(14) . . ?
I4 Bi1 I6 80.117(11) . . ?
I4 Bi1 I5 82.570(11) . . ?
I1 Bi1 I6 95.088(11) . . ?
I1 Bi1 I5 91.126(12) . . ?
I1 Bi1 I4 172.656(13) . . ?
I3 Bi1 I6 96.832(13) . . ?
I3 Bi1 I5 174.565(13) . . ?
I3 Bi1 I4 92.810(13) . . ?
I3 Bi1 I1 93.287(14) . . ?
I6 Bi2 I5 86.173(12) . . ?
I6 Bi2 I4 82.972(11) . . ?
I5 Bi2 I4 82.530(11) . . ?
I9 Bi2 I6 91.506(13) . . ?
I9 Bi2 I5 177.103(14) . . ?
I9 Bi2 I4 95.476(12) . . ?
I9 Bi2 I8 93.514(14) . . ?
I7 Bi2 I6 91.610(12) . . ?
I7 Bi2 I5 91.874(12) . . ?
I7 Bi2 I4 172.435(13) . . ?
I7 Bi2 I9 89.922(13) . . ?
I7 Bi2 I8 96.090(14) . . ?
I8 Bi2 I6 170.807(14) . . ?
I8 Bi2 I5 88.557(13) . . ?
I8 Bi2 I4 88.882(13) . . ?
Bi2 I6 Bi1 80.195(11) . . ?
Bi2 I5 Bi1 82.153(11) . . ?
Bi1 I4 Bi2 80.838(10) . . ?
C13 O2 C12 113.9(5) . . ?
C16 N4 H4 108.1 . . ?
C16 N4 C14 111.5(5) . . ?
C14 N4 H4 108.1 . . ?
C15 N4 H4 108.1 . . ?
C15 N4 C16 111.5(6) . . ?
C15 N4 C14 109.5(6) . . ?
C10 N3 H3 107.7 . . ?
C11 N3 H3 107.7 . . ?
C11 N3 C10 112.5(5) . . ?
C9 N3 H3 107.7 . . ?
C9 N3 C10 110.7(5) . . ?
C9 N3 C11 110.4(6) . . ?
C5 O1 C4 113.8(5) . . ?
C7 N2 H2 107.6 . . ?
C6 N2 H2 107.6 . . ?
C6 N2 C7 112.4(5) . . ?
C6 N2 C8 110.9(5) . . ?
C8 N2 H2 107.6 . . ?
C8 N2 C7 110.5(5) . . ?
C2 N1 H1 107.9 . . ?
C2 N1 C3 113.1(5) . . ?
C3 N1 H1 107.9 . . ?
C1 N1 H1 107.9 . . ?
C1 N1 C2 110.3(5) . . ?
C1 N1 C3 109.6(5) . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C13 H13A 110.7 . . ?
O2 C13 H13B 110.7 . . ?
O2 C13 C14 105.3(5) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
N2 C6 C5 111.9(5) . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
O1 C4 H4A 110.4 . . ?
O1 C4 H4B 110.4 . . ?
O1 C4 C3 106.7(5) . . ?
H4A C4 H4B 108.6 . . ?
C3 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
N3 C11 C12 111.1(5) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
O2 C12 C11 105.4(5) . . ?
O2 C12 H12A 110.7 . . ?
O2 C12 H12B 110.7 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
C13 C14 N4 110.7(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N1 C3 C4 111.7(5) . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C5 C6 106.3(5) . . ?
O1 C5 H5A 110.5 . . ?
O1 C5 H5B 110.5 . . ?
C6 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
