# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1996480'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2020-04-12 deposited with the CCDC.	2020-11-01 downloaded from the CCDC.
;
_vrf_PLAT974_shelx               
;
PROBLEM: Check Calcd Negative Resid. Density on       Bi1      -2.57 eA-3   
RESPONSE: Probably artifact caused by heavy atoms.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Bi2 I10 N4'
_chemical_formula_weight         2003.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   8.8336(8)
_cell_length_b                   10.7018(10)
_cell_length_c                   11.7936(10)
_cell_angle_alpha                114.450(2)
_cell_angle_beta                 99.704(2)
_cell_angle_gamma                100.092(2)
_cell_volume                     962.40(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17303
_cell_measurement_theta_min      2.1500
_cell_measurement_theta_max      36.6720

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.457
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    17.168
_shelx_estimated_absorpt_T_min   0.086
_shelx_estimated_absorpt_T_max   0.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.24852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported S'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10537
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.173
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3935
_reflns_number_gt                3840
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0486P)²+2.0789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3935
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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
Bi1 Bi 0.42900(2) 0.92841(2) 0.65505(2) 0.01426(8) Uani 1 1 d . . . . .
I3 I 0.74628(4) 1.00638(3) 0.57232(3) 0.01556(9) Uani 1 1 d . . . . .
I4 I 0.49842(4) 1.25485(3) 0.84606(3) 0.01827(9) Uani 1 1 d . . . . .
I2 I 0.35921(4) 0.62348(4) 0.45949(3) 0.01970(10) Uani 1 1 d . . . . .
I1 I 0.12244(4) 0.86934(4) 0.71901(3) 0.02032(10) Uani 1 1 d . . . . .
I5 I 0.62238(4) 0.87609(4) 0.85212(3) 0.02389(10) Uani 1 1 d . . . . .
N1 N 0.7373(6) 0.6325(5) 0.3645(4) 0.0212(9) Uani 1 1 d . . . . .
H1 H 0.687619 0.681746 0.418552 0.025 Uiso 1 1 calc R U . . .
N2 N 1.1398(5) 0.2396(5) -0.0512(4) 0.0189(9) Uani 1 1 d . . . . .
H2 H 1.192456 0.189720 -0.101860 0.023 Uiso 1 1 calc R U . . .
C8 C 0.9782(6) 0.3946(5) 0.1086(4) 0.0143(10) Uani 1 1 d . . . . .
C3 C 0.8931(6) 0.4783(5) 0.1980(5) 0.0154(10) Uani 1 1 d . . . . .
C7 C 1.1324(7) 0.4564(6) 0.1118(5) 0.0213(11) Uani 1 1 d . . . . .
H7 H 1.183212 0.554086 0.169853 0.026 Uiso 1 1 calc R U . . .
C9 C 0.9087(6) 0.2522(6) 0.0207(5) 0.0187(10) Uani 1 1 d . . . . .
H9 H 0.803418 0.207447 0.016135 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7442(6) 0.4136(6) 0.2036(5) 0.0176(10) Uani 1 1 d . . . . .
H2A H 0.695890 0.314607 0.149222 0.021 Uiso 1 1 calc R U . . .
C10 C 0.9896(6) 0.1751(6) -0.0595(5) 0.0185(10) Uani 1 1 d . . . . .
H10 H 0.940879 0.077862 -0.120057 0.022 Uiso 1 1 calc R U . . .
C5 C 0.8789(7) 0.7005(6) 0.3627(6) 0.0257(12) Uani 1 1 d . . . . .
H5 H 0.923709 0.799751 0.418110 0.031 Uiso 1 1 calc R U . . .
C1 C 0.6678(7) 0.4933(6) 0.2879(5) 0.0210(11) Uani 1 1 d . . . . .
H1A H 0.566594 0.449772 0.291649 0.025 Uiso 1 1 calc R U . . .
C4 C 0.9586(6) 0.6238(6) 0.2790(5) 0.0222(11) Uani 1 1 d . . . . .
H4 H 1.058901 0.670837 0.276674 0.027 Uiso 1 1 calc R U . . .
C6 C 1.2106(7) 0.3762(6) 0.0312(5) 0.0226(11) Uani 1 1 d . . . . .
H6 H 1.316173 0.418271 0.034120 0.027 Uiso 1 1 calc R U . . .


_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 2.9508(4) . ?
Bi1 I1 2.9640(4) . ?
Bi1 I2 2.9889(4) . ?
Bi1 I4 3.1503(4) . ?
Bi1 I3 3.2062(4) . ?
Bi1 I3 3.2562(4) 2_676 ?
N1 C1 1.338(7) . ?
N1 C5 1.341(8) . ?
N1 H1 0.8800 . ?
N2 C6 1.331(7) . ?
N2 C10 1.351(7) . ?
N2 H2 0.8800 . ?
C8 C9 1.387(7) . ?
C8 C7 1.394(7) . ?
C8 C3 1.484(8) . ?
C3 C4 1.392(7) . ?
C3 C2 1.401(7) . ?
C7 C6 1.368(8) . ?
C7 H7 0.9500 . ?
C9 C10 1.369(8) . ?
C9 H9 0.9500 . ?
C2 C1 1.377(7) . ?
C2 H2A 0.9500 . ?
C10 H10 0.9500 . ?
C5 C4 1.382(8) . ?
C5 H5 0.9500 . ?
C1 H1A 0.9500 . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?

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 I1 96.357(12) . . ?
I5 Bi1 I2 91.038(13) . . ?
I1 Bi1 I2 91.184(11) . . ?
I5 Bi1 I4 92.377(12) . . ?
I1 Bi1 I4 89.969(10) . . ?
I2 Bi1 I4 176.253(10) . . ?
I5 Bi1 I3 88.592(12) . . ?
I1 Bi1 I3 174.821(10) . . ?
I2 Bi1 I3 90.245(10) . . ?
I4 Bi1 I3 88.298(10) . . ?
I5 Bi1 I3 173.296(11) . 2_676 ?
I1 Bi1 I3 90.346(11) . 2_676 ?
I2 Bi1 I3 88.732(12) . 2_676 ?
I4 Bi1 I3 87.696(12) . 2_676 ?
I3 Bi1 I3 84.709(11) . 2_676 ?
Bi1 I3 Bi1 95.291(11) . 2_676 ?
C1 N1 C5 123.2(5) . . ?
C1 N1 H1 118.4 . . ?
C5 N1 H1 118.4 . . ?
C6 N2 C10 122.0(5) . . ?
C6 N2 H2 119.0 . . ?
C10 N2 H2 119.0 . . ?
C9 C8 C7 117.7(5) . . ?
C9 C8 C3 121.5(5) . . ?
C7 C8 C3 120.8(5) . . ?
C4 C3 C2 117.8(5) . . ?
C4 C3 C8 121.1(5) . . ?
C2 C3 C8 121.1(5) . . ?
C6 C7 C8 119.9(5) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C10 C9 C8 121.0(5) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C1 C2 C3 120.1(5) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
N2 C10 C9 118.9(5) . . ?
N2 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C5 C4 118.9(5) . . ?
N1 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N1 C1 C2 119.5(5) . . ?
N1 C1 H1A 120.3 . . ?
C2 C1 H1A 120.3 . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N2 C6 C7 120.4(5) . . ?
N2 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?

_refine_diff_density_max         1.954
_refine_diff_density_min         -2.692
_refine_diff_density_rms         0.320

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1996482'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2020-04-12 deposited with the CCDC.	2020-11-01 downloaded from the CCDC.
;

_vrf_PLAT416_shelx               
;
PROBLEM: Short Intra D-H..H-D       H2       ..H1       .       1.65 Ang.  
RESPONSE: Double protonation of terpyridine, a really strong base due to it
intramolecular H-bond
;
_vrf_PLAT417_shelx               
;
PROBLEM: Short Inter D-H..H-D       H2       ..H2B      .       1.99 Ang.  
RESPONSE: Double protonation of terpyridine, a really strong base due to it
intramolecular H-bond plus interaction with water molecule.
;
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.96A   From I3              3.04 eA-3   
RESPONSE: Probably artifact caused by heavy atoms.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H29 Bi I6 N6 O2'
_chemical_formula_weight         1475.97

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   10.666(2)
_cell_length_b                   10.822(2)
_cell_length_c                   10.947(2)
_cell_angle_alpha                81.045(4)
_cell_angle_beta                 61.715(4)
_cell_angle_gamma                61.460(4)
_cell_volume                     973.4(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    33122
_cell_measurement_theta_min      2.1240
_cell_measurement_theta_max      38.2920

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.518
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    9.320
_shelx_estimated_absorpt_T_min   0.315
_shelx_estimated_absorpt_T_max   0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported S'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26083
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3994
_reflns_number_gt                3913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0326P)²+13.4062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3994
_refine_ls_number_parameters     215
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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 0.0355(10) 0.8456(10) 0.2031(9) 0.0335(18) Uani 1 1 d . . . . .
H1A H 0.019950 0.937441 0.206810 0.040 Uiso 1 1 calc R U . . .
C2 C -0.0056(11) 0.8052(10) 0.1209(10) 0.038(2) Uani 1 1 d . . . . .
H2A H -0.052790 0.870998 0.070383 0.046 Uiso 1 1 calc R U . . .
C3 C 0.0223(11) 0.6680(11) 0.1123(9) 0.039(2) Uani 1 1 d . . . . .
H3A H -0.003488 0.640669 0.054507 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0886(10) 0.5715(10) 0.1897(9) 0.0359(19) Uani 1 1 d . . . . .
H4 H 0.108352 0.478553 0.183550 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1261(9) 0.6125(9) 0.2773(8) 0.0283(16) Uani 1 1 d . . . . .
C6 C 0.1912(9) 0.5232(8) 0.3708(9) 0.0285(16) Uani 1 1 d . . . . .
C7 C 0.2140(9) 0.3854(9) 0.3851(9) 0.0297(17) Uani 1 1 d . . . . .
H7 H 0.198359 0.342702 0.329696 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2605(11) 0.3140(9) 0.4837(10) 0.039(2) Uani 1 1 d . . . . .
H8 H 0.273372 0.222573 0.498688 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2876(10) 0.3794(10) 0.5601(10) 0.037(2) Uani 1 1 d . . . . .
H9 H 0.319312 0.332409 0.627108 0.045 Uiso 1 1 calc R U . . .
C10 C 0.2672(9) 0.5180(9) 0.5362(8) 0.0288(17) Uani 1 1 d . . . . .
C11 C 0.2996(9) 0.5932(9) 0.6119(9) 0.0318(18) Uani 1 1 d . . . . .
C12 C 0.3401(11) 0.5375(10) 0.7189(9) 0.038(2) Uani 1 1 d . . . . .
H12 H 0.350859 0.448318 0.744770 0.046 Uiso 1 1 calc R U . . .
C13 C 0.3643(11) 0.6151(11) 0.7863(10) 0.040(2) Uani 1 1 d . . . . .
H13 H 0.389811 0.579236 0.858985 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3504(10) 0.7478(9) 0.7451(9) 0.0330(18) Uani 1 1 d . . . . .
H14 H 0.367092 0.801560 0.788822 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3114(10) 0.7970(9) 0.6378(9) 0.0331(18) Uani 1 1 d . . . . .
H15 H 0.301541 0.885234 0.608745 0.040 Uiso 1 1 calc R U . . .
N1 N 0.0996(8) 0.7483(7) 0.2793(7) 0.0281(14) Uani 1 1 d D . . . .
H1 H 0.124719 0.774020 0.331337 0.034 Uiso 0.31(7) 1 calc R U P A 1
N2 N 0.2180(8) 0.5866(7) 0.4439(7) 0.0270(14) Uani 1 1 d . . . . .
H2 H 0.203367 0.671920 0.431115 0.032 Uiso 1 1 calc R U . . .
N3 N 0.2873(8) 0.7200(7) 0.5743(7) 0.0298(14) Uani 1 1 d D . . . .
H3 H 0.263206 0.753446 0.507421 0.036 Uiso 0.19(7) 1 calc R U P A 2
I1 I 0.86888(5) 0.82869(5) -0.17020(5) 0.02369(12) Uani 1 1 d . . . . .
I2 I 0.52447(6) 0.95314(5) 0.27375(5) 0.03010(13) Uani 1 1 d . . . . .
I3 I 0.48314(6) 0.72011(5) 0.02674(5) 0.02876(13) Uani 1 1 d . . . . .
Bi1 Bi 0.500000 1.000000 0.000000 0.02041(11) Uani 1 2 d S . P . .
O1 O 0.1497(8) 0.9002(6) 0.4178(6) 0.0320(12) Uani 1 1 d D . . . .
H1B H 0.13(3) 0.86(2) 0.356(14) 0.048 Uiso 0.38(14) 1 d D U P A 2
H2B H 0.212(15) 0.844(14) 0.461(14) 0.048 Uiso 0.62(14) 1 d D U P A 1
H1C H 0.206(11) 0.945(9) 0.361(9) 0.048 Uiso 1 1 d D U . . .


_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 1.361(11) . ?
C1 C2 1.368(13) . ?
C1 H1A 0.9300 . ?
C2 C3 1.377(14) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(13) . ?
C3 H3A 0.9300 . ?
C4 C5 1.394(12) . ?
C4 H4 0.9300 . ?
C5 N1 1.359(11) . ?
C5 C6 1.479(11) . ?
C6 N2 1.329(11) . ?
C6 C7 1.388(11) . ?
C7 C8 1.375(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(12) . ?
C9 H9 0.9300 . ?
C10 N2 1.321(10) . ?
C10 C11 1.489(12) . ?
C11 N3 1.331(11) . ?
C11 C12 1.390(12) . ?
C12 C13 1.378(13) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(12) . ?
C14 H14 0.9300 . ?
C15 N3 1.341(11) . ?
C15 H15 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?
N3 H3 0.8600 . ?
I1 Bi1 3.0899(7) . ?
I2 Bi1 3.0738(8) . ?
I3 Bi1 3.0800(7) . ?
O1 H1B 0.94(5) . ?
O1 H2B 0.93(4) . ?
O1 H1C 0.90(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 118.4(8) . . ?
N1 C1 H1A 120.8 . . ?
C2 C1 H1A 120.8 . . ?
C1 C2 C3 120.6(8) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 119.7(8) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.2(9) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 117.6(8) . . ?
N1 C5 C6 115.8(7) . . ?
C4 C5 C6 126.6(8) . . ?
N2 C6 C7 123.1(8) . . ?
N2 C6 C5 115.4(7) . . ?
C7 C6 C5 121.4(7) . . ?
C8 C7 C6 117.8(8) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C9 119.2(8) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 119.6(8) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
N2 C10 C9 120.4(8) . . ?
N2 C10 C11 117.2(8) . . ?
C9 C10 C11 122.4(8) . . ?
N3 C11 C12 119.6(8) . . ?
N3 C11 C10 117.4(7) . . ?
C12 C11 C10 123.1(8) . . ?
C13 C12 C11 119.6(9) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.6(8) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 118.1(8) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
N3 C15 C14 121.2(8) . . ?
N3 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C5 N1 C1 123.4(7) . . ?
C5 N1 H1 118.3 . . ?
C1 N1 H1 118.3 . . ?
C10 N2 C6 119.8(7) . . ?
C10 N2 H2 120.1 . . ?
C6 N2 H2 120.1 . . ?
C11 N3 C15 121.8(7) . . ?
C11 N3 H3 119.1 . . ?
C15 N3 H3 119.1 . . ?
I2 Bi1 I2 180.00(2) 2_675 . ?
I2 Bi1 I3 87.717(15) 2_675 2_675 ?
I2 Bi1 I3 92.283(15) . 2_675 ?
I2 Bi1 I3 92.282(15) 2_675 . ?
I2 Bi1 I3 87.718(15) . . ?
I3 Bi1 I3 180.00(2) 2_675 . ?
I2 Bi1 I1 89.025(17) 2_675 . ?
I2 Bi1 I1 90.975(17) . . ?
I3 Bi1 I1 91.962(17) 2_675 . ?
I3 Bi1 I1 88.037(17) . . ?
I2 Bi1 I1 90.975(17) 2_675 2_675 ?
I2 Bi1 I1 89.025(17) . 2_675 ?
I3 Bi1 I1 88.037(17) 2_675 2_675 ?
I3 Bi1 I1 91.963(17) . 2_675 ?
I1 Bi1 I1 180.0 . 2_675 ?
H1B O1 H1C 102(7) . . ?
H2B O1 H1C 102(6) . . ?

_refine_diff_density_max         3.107
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.198

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

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1996481'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2020-04-12 deposited with the CCDC.	2020-11-01 downloaded from the CCDC.
;

_vrf_PLAT413_shelx               
;
PROBLEM: Short Inter XH3 .. XHn     H15B     ..H40B     .       1.95 Ang.  
RESPONSE: CH3---CH3 interaction caused by strong phenantroline pi-stacking
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H39 Bi2 I9 N6'
_chemical_formula_weight         2187.85

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   23.5530(16)
_cell_length_b                   10.4348(7)
_cell_length_c                   21.9237(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5388.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    70499
_cell_measurement_theta_min      1.8670
_cell_measurement_theta_max      37.0260

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.697
_exptl_crystal_F_000             3904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.132
_exptl_absorpt_coefficient_mu    11.714
_shelx_estimated_absorpt_T_min   0.135
_shelx_estimated_absorpt_T_max   0.307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported S'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77406
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11011
_reflns_number_gt                10653
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0646P)²+7.5757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11011
_refine_ls_number_parameters     532
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.80883(2) 0.19890(4) 0.56025(2) 0.03247(9) Uani 1 1 d . . . . .
Bi2 Bi 0.67184(2) 0.04409(4) 0.65984(2) 0.03271(9) Uani 1 1 d . . . . .
I6 I 0.68418(3) 0.10152(7) 0.50967(3) 0.03985(16) Uani 1 1 d . . . . .
I4 I 0.72393(3) 0.32926(7) 0.66264(4) 0.04428(17) Uani 1 1 d . . . . .
I5 I 0.80703(3) -0.03331(7) 0.65183(4) 0.04525(18) Uani 1 1 d . . . . .
I3 I 0.87175(3) 0.02686(9) 0.47609(4) 0.0513(2) Uani 1 1 d . . . . .
I1 I 0.90760(4) 0.30414(10) 0.62141(4) 0.0543(2) Uani 1 1 d . . . . .
I2 I 0.81499(4) 0.41602(9) 0.47048(4) 0.0531(2) Uani 1 1 d . . . . .
I8 I 0.55709(3) 0.14401(9) 0.66114(5) 0.0573(2) Uani 1 1 d . . . . .
I9 I 0.63266(4) -0.22708(8) 0.63860(5) 0.0571(2) Uani 1 1 d . . . . .
I7 I 0.67681(4) 0.00754(10) 0.79207(4) 0.0556(2) Uani 1 1 d . . . . .
C30 C 0.7245(6) 0.7641(11) 0.4571(6) 0.046(3) Uani 1 1 d . . . . .
C19 C 0.6227(5) 0.4722(10) 0.4418(6) 0.044(3) Uani 1 1 d . . . . .
N6 N 0.5545(5) 0.8244(9) 0.4609(5) 0.046(2) Uani 1 1 d . . . . .
N2 N 0.5647(4) 0.1799(8) 0.3797(5) 0.041(2) Uani 1 1 d . . . . .
H2 H 0.595398 0.172290 0.402250 0.049 Uiso 1 1 calc R U . . .
N4 N 0.4868(4) 0.5476(10) 0.3677(4) 0.042(2) Uani 1 1 d . . . . .
N1 N 0.6685(4) 0.1549(8) 0.3266(4) 0.0364(19) Uani 1 1 d . . . . .
C20 C 0.5657(5) 0.5009(10) 0.4326(5) 0.039(2) Uani 1 1 d . . . . .
C7 C 0.5681(5) 0.1791(10) 0.3170(5) 0.040(2) Uani 1 1 d . . . . .
N3 N 0.5299(4) 0.5124(9) 0.4811(5) 0.039(2) Uani 1 1 d . . . . .
H3 H 0.494013 0.530973 0.474066 0.047 Uiso 1 1 calc R U . . .
C28 C 0.6596(6) 0.4613(11) 0.3898(7) 0.049(3) Uani 1 1 d . . . . .
H28 H 0.698284 0.438103 0.395132 0.059 Uiso 1 1 calc R U . . .
C27 C 0.6389(6) 0.4841(12) 0.3336(8) 0.055(3) Uani 1 1 d . . . . .
H27 H 0.664267 0.482619 0.299922 0.066 Uiso 1 1 calc R U . . .
C39 C 0.4988(6) 0.8469(12) 0.4642(6) 0.049(3) Uani 1 1 d . . . . .
C8 C 0.5199(6) 0.1860(12) 0.2784(7) 0.053(3) Uani 1 1 d . . . . .
C25 C 0.4656(6) 0.5660(13) 0.3120(6) 0.049(3) Uani 1 1 d . . . . .
C37 C 0.4916(6) 0.8765(12) 0.3558(7) 0.054(3) Uani 1 1 d . . . . .
H37 H 0.469750 0.893507 0.320291 0.064 Uiso 1 1 calc R U . . .
C22 C 0.5811(6) 0.5100(10) 0.3231(6) 0.043(3) Uani 1 1 d . . . . .
C35 C 0.5796(5) 0.8290(9) 0.4061(5) 0.039(2) Uani 1 1 d . . . . .
C42 C 0.6365(7) 0.8303(12) 0.2927(6) 0.055(3) Uani 1 1 d . . . . .
H42 H 0.655395 0.830493 0.254397 0.066 Uiso 1 1 calc R U . . .
C31 C 0.7544(6) 0.7596(13) 0.4029(7) 0.057(3) Uani 1 1 d . . . . .
H31 H 0.794037 0.742391 0.403287 0.068 Uiso 1 1 calc R U . . .
N5 N 0.6691(4) 0.7847(9) 0.4556(5) 0.042(2) Uani 1 1 d . . . . .
H5 H 0.650503 0.784533 0.490406 0.050 Uiso 1 1 calc R U . . .
C5 C 0.6288(6) 0.1568(12) 0.2272(6) 0.052(3) Uani 1 1 d . . . . .
C2 C 0.7211(6) 0.1445(12) 0.3066(7) 0.049(3) Uani 1 1 d . . . . .
C36 C 0.5499(6) 0.8547(9) 0.3507(6) 0.043(3) Uani 1 1 d . . . . .
C38 C 0.4659(7) 0.8736(13) 0.4115(7) 0.057(3) Uani 1 1 d . . . . .
H38 H 0.426326 0.889265 0.414995 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5469(6) 0.4966(11) 0.5389(5) 0.043(3) Uani 1 1 d . . . . .
C41 C 0.5800(6) 0.8538(11) 0.2943(6) 0.048(3) Uani 1 1 d . . . . .
H41 H 0.560213 0.869908 0.257364 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7295(7) 0.1357(14) 0.2437(7) 0.060(4) Uani 1 1 d . . . . .
H3A H 0.766726 0.125010 0.227838 0.072 Uiso 1 1 calc R U . . .
C11 C 0.5140(6) 0.1925(11) 0.4052(7) 0.050(3) Uani 1 1 d . . . . .
C14 C 0.5800(8) 0.1645(15) 0.1900(7) 0.064(4) Uani 1 1 d . . . . .
H14 H 0.584058 0.160292 0.146893 0.076 Uiso 1 1 calc R U . . .
C18 C 0.6414(6) 0.4552(12) 0.5020(7) 0.052(3) Uani 1 1 d . . . . .
H18 H 0.680033 0.434890 0.509676 0.063 Uiso 1 1 calc R U . . .
C23 C 0.5564(7) 0.5316(13) 0.2659(6) 0.054(3) Uani 1 1 d . . . . .
H23 H 0.579452 0.528762 0.230345 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5111(8) 0.1907(14) 0.4727(8) 0.065(4) Uani 1 1 d . . . . .
H12A H 0.471517 0.200790 0.485683 0.097 Uiso 1 1 calc R U . . .
H12B H 0.525909 0.108987 0.487839 0.097 Uiso 1 1 calc R U . . .
H12C H 0.533874 0.261271 0.489121 0.097 Uiso 1 1 calc R U . . .
C29 C 0.7511(7) 0.7443(16) 0.5174(7) 0.063(4) Uani 1 1 d . . . . .
H29A H 0.791946 0.730192 0.512150 0.094 Uiso 1 1 calc R U . . .
H29B H 0.744925 0.820160 0.542857 0.094 Uiso 1 1 calc R U . . .
H29C H 0.734087 0.669241 0.537109 0.094 Uiso 1 1 calc R U . . .
C24 C 0.5001(7) 0.5564(14) 0.2606(6) 0.058(3) Uani 1 1 d . . . . .
H24 H 0.483958 0.567485 0.221240 0.069 Uiso 1 1 calc R U . . .
C15 C 0.5050(8) 0.5119(15) 0.5875(6) 0.061(4) Uani 1 1 d . . . . .
H15A H 0.523263 0.497705 0.627053 0.092 Uiso 1 1 calc R U . . .
H15B H 0.489264 0.598739 0.586043 0.092 Uiso 1 1 calc R U . . .
H15C H 0.474390 0.449352 0.581865 0.092 Uiso 1 1 calc R U . . .
C9 C 0.4672(6) 0.2028(14) 0.3082(9) 0.063(4) Uani 1 1 d . . . . .
H9 H 0.433644 0.213750 0.284750 0.075 Uiso 1 1 calc R U . . .
C40 C 0.4717(7) 0.8471(17) 0.5269(7) 0.066(4) Uani 1 1 d . . . . .
H40A H 0.431005 0.864713 0.522982 0.099 Uiso 1 1 calc R U . . .
H40B H 0.477179 0.763263 0.546135 0.099 Uiso 1 1 calc R U . . .
H40C H 0.489423 0.913594 0.552108 0.099 Uiso 1 1 calc R U . . .
C33 C 0.6687(6) 0.8052(12) 0.3467(6) 0.047(3) Uani 1 1 d . . . . .
C34 C 0.6383(5) 0.8065(9) 0.4021(5) 0.038(2) Uani 1 1 d . . . . .
C4 C 0.6835(7) 0.1427(14) 0.2042(7) 0.061(4) Uani 1 1 d . . . . .
H4 H 0.689462 0.137835 0.161400 0.073 Uiso 1 1 calc R U . . .
C32 C 0.7264(7) 0.7804(15) 0.3478(7) 0.063(4) Uani 1 1 d . . . . .
H32 H 0.747084 0.777404 0.310609 0.076 Uiso 1 1 calc R U . . .
C13 C 0.5278(8) 0.1776(16) 0.2144(8) 0.069(4) Uani 1 1 d . . . . .
H13 H 0.495705 0.181249 0.188227 0.082 Uiso 1 1 calc R U . . .
C1 C 0.7688(6) 0.1391(15) 0.3503(7) 0.057(3) Uani 1 1 d . . . . .
H1A H 0.804679 0.131361 0.327894 0.086 Uiso 1 1 calc R U . . .
H1B H 0.769350 0.217564 0.374846 0.086 Uiso 1 1 calc R U . . .
H1C H 0.764140 0.064727 0.377146 0.086 Uiso 1 1 calc R U . . .
C10 C 0.4642(6) 0.2033(14) 0.3699(11) 0.070(5) Uani 1 1 d . . . . .
H10 H 0.428338 0.210978 0.389426 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6042(6) 0.4677(10) 0.5499(7) 0.054(4) Uani 1 1 d . . . . .
H17 H 0.617290 0.456863 0.590557 0.065 Uiso 1 1 calc R U . . .
C26 C 0.4036(7) 0.596(2) 0.3069(8) 0.077(5) Uani 1 1 d . . . . .
H26A H 0.393547 0.607247 0.263876 0.116 Uiso 1 1 calc R U . . .
H26B H 0.381487 0.525124 0.324148 0.116 Uiso 1 1 calc R U . . .
H26C H 0.395275 0.674899 0.329360 0.116 Uiso 1 1 calc R U . . .
C21 C 0.5429(5) 0.5195(9) 0.3723(5) 0.036(2) Uani 1 1 d . . . . .
C6 C 0.6222(5) 0.1637(9) 0.2900(5) 0.038(2) 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 I1 2.9009(9) . ?
Bi1 I3 2.9704(9) . ?
Bi1 I2 3.0045(9) . ?
Bi1 I5 3.1472(8) . ?
Bi1 I6 3.2987(8) . ?
Bi1 I4 3.2999(9) . ?
Bi2 I8 2.8970(9) . ?
Bi2 I7 2.9263(9) . ?
Bi2 I9 3.0125(9) . ?
Bi2 I4 3.2192(8) . ?
Bi2 I5 3.2896(8) . ?
Bi2 I6 3.3589(9) . ?
C30 N5 1.322(17) . ?
C30 C31 1.382(19) . ?
C30 C29 1.478(19) . ?
C19 C18 1.403(19) . ?
C19 C20 1.389(17) . ?
C19 C28 1.44(2) . ?
N6 C35 1.341(16) . ?
N6 C39 1.334(18) . ?
N2 C11 1.325(17) . ?
N2 C7 1.376(16) . ?
N2 H2 0.8800 . ?
N4 C25 1.334(16) . ?
N4 C21 1.357(15) . ?
N1 C2 1.319(16) . ?
N1 C6 1.358(14) . ?
C20 N3 1.361(16) . ?
C20 C21 1.440(16) . ?
C7 C6 1.414(18) . ?
C7 C8 1.417(17) . ?
N3 C16 1.340(14) . ?
N3 H3 0.8800 . ?
C28 C27 1.35(2) . ?
C28 H28 0.9500 . ?
C27 C22 1.409(19) . ?
C27 H27 0.9500 . ?
C39 C38 1.42(2) . ?
C39 C40 1.516(18) . ?
C8 C9 1.41(2) . ?
C8 C13 1.42(2) . ?
C25 C24 1.393(19) . ?
C25 C26 1.50(2) . ?
C37 C38 1.36(2) . ?
C37 C36 1.39(2) . ?
C37 H37 0.9500 . ?
C22 C23 1.40(2) . ?
C22 C21 1.409(17) . ?
C35 C34 1.404(17) . ?
C35 C36 1.428(17) . ?
C42 C41 1.35(2) . ?
C42 C33 1.43(2) . ?
C42 H42 0.9500 . ?
C31 C32 1.39(2) . ?
C31 H31 0.9500 . ?
N5 C34 1.398(17) . ?
N5 H5 0.8800 . ?
C5 C4 1.39(2) . ?
C5 C6 1.389(19) . ?
C5 C14 1.41(2) . ?
C2 C3 1.40(2) . ?
C2 C1 1.48(2) . ?
C36 C41 1.425(19) . ?
C38 H38 0.9500 . ?
C16 C17 1.404(19) . ?
C16 C15 1.46(2) . ?
C41 H41 0.9500 . ?
C3 C4 1.39(2) . ?
C3 H3A 0.9500 . ?
C11 C10 1.41(2) . ?
C11 C12 1.48(2) . ?
C14 C13 1.35(3) . ?
C14 H14 0.9500 . ?
C18 C17 1.37(2) . ?
C18 H18 0.9500 . ?
C23 C24 1.36(2) . ?
C23 H23 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C24 H24 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9 C10 1.35(3) . ?
C9 H9 0.9500 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C33 C32 1.38(2) . ?
C33 C34 1.410(17) . ?
C4 H4 0.9500 . ?
C32 H32 0.9500 . ?
C13 H13 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C10 H10 0.9500 . ?
C17 H17 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
I1 Bi1 I3 96.65(3) . . ?
I1 Bi1 I2 88.77(3) . . ?
I3 Bi1 I2 91.42(3) . . ?
I1 Bi1 I5 90.42(3) . . ?
I3 Bi1 I5 86.43(3) . . ?
I2 Bi1 I5 177.61(3) . . ?
I1 Bi1 I6 170.29(3) . . ?
I3 Bi1 I6 92.81(2) . . ?
I2 Bi1 I6 93.16(2) . . ?
I5 Bi1 I6 88.01(2) . . ?
I1 Bi1 I4 90.89(2) . . ?
I3 Bi1 I4 166.92(3) . . ?
I2 Bi1 I4 99.44(3) . . ?
I5 Bi1 I4 82.83(2) . . ?
I6 Bi1 I4 79.41(2) . . ?
I8 Bi2 I7 94.27(3) . . ?
I8 Bi2 I9 93.08(3) . . ?
I7 Bi2 I9 92.46(3) . . ?
I8 Bi2 I4 91.30(3) . . ?
I7 Bi2 I4 94.95(3) . . ?
I9 Bi2 I4 171.09(3) . . ?
I8 Bi2 I5 172.70(3) . . ?
I7 Bi2 I5 88.97(3) . . ?
I9 Bi2 I5 93.30(2) . . ?
I4 Bi2 I5 81.90(2) . . ?
I8 Bi2 I6 91.50(3) . . ?
I7 Bi2 I6 172.21(3) . . ?
I9 Bi2 I6 92.44(3) . . ?
I4 Bi2 I6 79.68(2) . . ?
I5 Bi2 I6 84.71(2) . . ?
Bi1 I6 Bi2 78.610(17) . . ?
Bi2 I4 Bi1 80.615(19) . . ?
Bi1 I5 Bi2 81.841(19) . . ?
N5 C30 C31 119.2(13) . . ?
N5 C30 C29 117.6(12) . . ?
C31 C30 C29 123.1(13) . . ?
C18 C19 C20 117.8(13) . . ?
C18 C19 C28 123.1(12) . . ?
C20 C19 C28 119.2(12) . . ?
C35 N6 C39 118.4(11) . . ?
C11 N2 C7 118.3(11) . . ?
C11 N2 H2 120.9 . . ?
C7 N2 H2 120.9 . . ?
C25 N4 C21 117.6(11) . . ?
C2 N1 C6 124.4(11) . . ?
N3 C20 C19 120.4(11) . . ?
N3 C20 C21 118.2(10) . . ?
C19 C20 C21 121.4(12) . . ?
N2 C7 C6 118.1(10) . . ?
N2 C7 C8 123.3(12) . . ?
C6 C7 C8 118.5(11) . . ?
C16 N3 C20 122.8(11) . . ?
C16 N3 H3 118.6 . . ?
C20 N3 H3 118.6 . . ?
C27 C28 C19 119.5(12) . . ?
C27 C28 H28 120.2 . . ?
C19 C28 H28 120.2 . . ?
C28 C27 C22 122.3(14) . . ?
C28 C27 H27 118.9 . . ?
C22 C27 H27 118.9 . . ?
N6 C39 C38 121.8(12) . . ?
N6 C39 C40 117.6(13) . . ?
C38 C39 C40 120.5(13) . . ?
C9 C8 C13 125.4(14) . . ?
C9 C8 C7 115.7(14) . . ?
C13 C8 C7 118.8(14) . . ?
N4 C25 C24 120.9(13) . . ?
N4 C25 C26 117.6(12) . . ?
C24 C25 C26 121.5(13) . . ?
C38 C37 C36 120.3(14) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C23 C22 C21 114.2(12) . . ?
C23 C22 C27 125.4(13) . . ?
C21 C22 C27 120.4(13) . . ?
N6 C35 C34 118.9(11) . . ?
N6 C35 C36 123.6(11) . . ?
C34 C35 C36 117.5(11) . . ?
C41 C42 C33 122.2(13) . . ?
C41 C42 H42 118.9 . . ?
C33 C42 H42 118.9 . . ?
C32 C31 C30 119.8(13) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C30 N5 C34 124.1(10) . . ?
C30 N5 H5 118.0 . . ?
C34 N5 H5 118.0 . . ?
C4 C5 C6 117.9(13) . . ?
C4 C5 C14 123.4(14) . . ?
C6 C5 C14 118.7(14) . . ?
N1 C2 C3 117.8(13) . . ?
N1 C2 C1 120.2(12) . . ?
C3 C2 C1 122.1(13) . . ?
C37 C36 C41 124.2(12) . . ?
C37 C36 C35 116.4(12) . . ?
C41 C36 C35 119.4(12) . . ?
C37 C38 C39 119.4(14) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
N3 C16 C17 118.4(13) . . ?
N3 C16 C15 118.4(12) . . ?
C17 C16 C15 123.2(12) . . ?
C42 C41 C36 121.0(12) . . ?
C42 C41 H41 119.5 . . ?
C36 C41 H41 119.5 . . ?
C2 C3 C4 120.2(14) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
N2 C11 C10 121.7(14) . . ?
N2 C11 C12 117.5(14) . . ?
C10 C11 C12 120.7(14) . . ?
C13 C14 C5 121.2(15) . . ?
C13 C14 H14 119.4 . . ?
C5 C14 H14 119.4 . . ?
C17 C18 C19 120.5(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C24 C23 C22 120.9(12) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C24 C25 121.0(13) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C9 C8 120.5(14) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C32 C33 C34 119.1(13) . . ?
C32 C33 C42 124.7(13) . . ?
C34 C33 C42 116.2(13) . . ?
N5 C34 C35 119.1(10) . . ?
N5 C34 C33 117.1(11) . . ?
C35 C34 C33 123.8(12) . . ?
C5 C4 C3 120.2(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C31 C32 C33 120.6(13) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C14 C13 C8 121.3(14) . . ?
C14 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
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 . . ?
C9 C10 C11 120.3(14) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C18 C17 C16 120.1(12) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N4 C21 C22 125.4(11) . . ?
N4 C21 C20 117.4(11) . . ?
C22 C21 C20 117.1(11) . . ?
N1 C6 C5 119.5(12) . . ?
N1 C6 C7 119.0(10) . . ?
C5 C6 C7 121.5(11) . . ?

_refine_diff_density_max         1.185
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.114

