# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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. 
# 
#######################################################################

data_cmc21
_database_code_depnum_ccdc_archive 'CCDC 1855907'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H15 Bi2 I9 N6'
_chemical_formula_weight         1695.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

_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, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   8.6920(2)
_cell_length_b                   15.0550(2)
_cell_length_c                   21.9675(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2874.62(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    189.9(2)
_cell_measurement_reflns_used    5047
_cell_measurement_theta_min      2.8950
_cell_measurement_theta_max      25.6400

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.917
_exptl_crystal_F_000             2872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    21.893
_exptl_absorpt_correction_T_min  0.41979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.630
_oxdiff_exptl_absorpt_empirical_full_max 1.674
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      189.9(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            12711
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.782
_diffrn_reflns_theta_max         29.343
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3803
_reflns_number_gt                3157
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_max     0.895
_reflns_Friedel_fraction_full    0.965

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

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1200P)²+4.0000P] 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 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3803
_refine_ls_number_parameters     84
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.2060
_refine_ls_wR_factor_gt          0.1929
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_restrained_S_all      1.204
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.006

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 0.5000 0.15715(16) 0.13913(17) 0.0445(5) Uani 1 2 d S T P . .
Bi2 Bi 0.5000 0.17589(17) 0.32837(17) 0.0464(5) Uani 1 2 d S T P . .
I1 I 0.7477(5) 0.0662(4) 0.0693(2) 0.0937(15) Uani 1 1 d . . . . .
I2 I 0.5000 0.3128(4) 0.0610(3) 0.0679(13) Uani 1 2 d S T P . .
I3 I 0.5000 0.0013(4) 0.2414(3) 0.0595(12) Uani 1 2 d S T P . .
I4 I 0.2512(3) 0.2480(3) 0.2295(2) 0.0668(11) Uani 1 1 d . . . . .
I5 I 0.2518(4) 0.1030(4) 0.4039(2) 0.0814(12) Uani 1 1 d . . . . .
I6 I 0.5000 0.3486(5) 0.3934(3) 0.099(2) Uani 1 2 d S T P . .
C11 C 0.0000 -0.024(5) 0.276(2) 0.081(17) Uiso 0.5 2 d DS . P . .
H11 H 0.0153 -0.0717 0.3021 0.098 Uiso 0.25 1 calc R U P . .
C12 C 0.0000 0.050(4) 0.220(3) 0.081(17) Uiso 0.5 2 d DS . P . .
H12 H -0.0154 0.0844 0.1855 0.098 Uiso 0.25 1 calc R U P . .
N12 N 0.023(10) -0.035(4) 0.218(2) 0.081(17) Uiso 0.5 1 d D . P . .
H12A H 0.0368 -0.0646 0.2508 0.098 Uiso 0.5 1 calc R U P . .
H12B H 0.0242 -0.0616 0.1832 0.098 Uiso 0.5 1 calc R U P . .
N21 N 0.0000 0.058(6) 0.295(3) 0.081(17) Uiso 0.5 2 d DS . P . .
H21A H -0.0145 0.1004 0.2691 0.098 Uiso 0.25 1 calc R U P . .
H21B H 0.0145 0.0694 0.3325 0.098 Uiso 0.25 1 calc R U P . .
N22 N 0.0000 0.085(5) 0.274(4) 0.081(17) Uiso 0.5 2 d DS . P . .
H22A H 0.0146 0.0515 0.3058 0.098 Uiso 0.25 1 calc R U P . .
H22B H -0.0146 0.1409 0.2791 0.098 Uiso 0.25 1 calc R U P . .
C2 C 0.5000 0.108(8) -0.061(5) 0.17(3) Uiso 1 2 d DS . P . .
H2 H 0.5000 0.0645 -0.0309 0.210 Uiso 1 2 calc R U P . .
C3 C 0.5000 -0.167(5) 0.068(3) 0.14(2) Uiso 1 2 d DS . P . .
H3 H 0.5000 -0.1486 0.0277 0.166 Uiso 1 2 calc R U P . .
N4 N 0.5000 -0.108(5) 0.111(4) 0.14(2) Uiso 1 2 d DS . P . .
H4A H 0.5000 -0.1247 0.1489 0.166 Uiso 1 2 calc R U P . .
H4B H 0.5000 -0.0522 0.1027 0.166 Uiso 1 2 calc R U P . .
N3 N 0.6294(8) 0.139(6) -0.082(3) 0.17(3) Uiso 1 1 d D . . . .
H3A H 0.6293 0.1790 -0.1096 0.210 Uiso 1 1 calc R U . . .
H3B H 0.7151 0.1185 -0.0681 0.210 Uiso 1 1 calc R U . . .
N5 N 0.5000 -0.251(5) 0.081(4) 0.14(2) Uiso 1 2 d DS . P . .
H5A H 0.5000 -0.2675 0.1189 0.166 Uiso 1 2 calc R U P . .
H5B H 0.5000 -0.2897 0.0528 0.166 Uiso 1 2 calc R U P . .


_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 I2 2.904(6) . ?
Bi1 I1 2.977(3) 4_655 ?
Bi1 I1 2.977(3) . ?
Bi1 I4 3.239(3) . ?
Bi1 I4 3.239(3) 4_655 ?
Bi1 I3 3.248(5) . ?
Bi2 I5 2.934(3) . ?
Bi2 I5 2.934(3) 4_655 ?
Bi2 I6 2.967(7) . ?
Bi2 I3 3.249(6) . ?
Bi2 I4 3.251(3) 4_655 ?
Bi2 I4 3.251(3) . ?
C11 N21 1.300(7) . ?
C11 N12 1.301(7) 4 ?
C11 H11 0.9300 . ?
C12 N12 1.300(7) . ?
C12 N22 1.300(7) . ?
C12 H12 0.9300 . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N21 H21A 0.8600 . ?
N21 H21B 0.8600 . ?
N22 H22A 0.8600 . ?
N22 H22B 0.8600 . ?
C2 N3 1.299(7) . ?
C2 N3 1.299(7) 4_655 ?
C2 H2 0.9300 . ?
C3 N5 1.299(7) . ?
C3 N4 1.299(7) . ?
C3 H3 0.9300 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?

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
I2 Bi1 I1 93.83(12) . 4_655 ?
I2 Bi1 I1 93.83(12) . . ?
I1 Bi1 I1 92.7(2) 4_655 . ?
I2 Bi1 I4 91.23(13) . . ?
I1 Bi1 I4 91.56(14) 4_655 . ?
I1 Bi1 I4 173.18(12) . . ?
I2 Bi1 I4 91.23(13) . 4_655 ?
I1 Bi1 I4 173.18(12) 4_655 4_655 ?
I1 Bi1 I4 91.56(14) . 4_655 ?
I4 Bi1 I4 83.75(16) . 4_655 ?
I2 Bi1 I3 172.45(17) . . ?
I1 Bi1 I3 91.38(12) 4_655 . ?
I1 Bi1 I3 91.38(12) . . ?
I4 Bi1 I3 83.17(11) . . ?
I4 Bi1 I3 83.17(11) 4_655 . ?
I5 Bi2 I5 94.66(19) . 4_655 ?
I5 Bi2 I6 93.18(14) . . ?
I5 Bi2 I6 93.18(14) 4_655 . ?
I5 Bi2 I3 91.72(13) . . ?
I5 Bi2 I3 91.72(13) 4_655 . ?
I6 Bi2 I3 172.77(17) . . ?
I5 Bi2 I4 172.53(12) . 4_655 ?
I5 Bi2 I4 90.77(11) 4_655 4_655 ?
I6 Bi2 I4 91.64(14) . 4_655 ?
I3 Bi2 I4 82.97(12) . 4_655 ?
I5 Bi2 I4 90.77(11) . . ?
I5 Bi2 I4 172.53(12) 4_655 . ?
I6 Bi2 I4 91.65(14) . . ?
I3 Bi2 I4 82.97(12) . . ?
I4 Bi2 I4 83.38(13) 4_655 . ?
Bi2 I3 Bi1 79.78(14) . . ?
Bi1 I4 Bi2 79.88(6) . . ?
N21 C11 N12 115.4(9) . 4 ?
N21 C11 H11 122.5 . . ?
N12 C11 H11 122.1 4 . ?
N12 C12 N22 115.6(9) . . ?
N12 C12 H12 122.2 . . ?
N22 C12 H12 122.2 . . ?
C12 N12 H12A 120.0 . . ?
C12 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C11 N21 H21A 120.2 . . ?
C11 N21 H21B 119.8 . . ?
H21A N21 H21B 120.0 . . ?
C12 N22 H22A 120.0 . . ?
C12 N22 H22B 120.0 . . ?
H22A N22 H22B 120.0 . . ?
N3 C2 N3 119.9(16) . 4_655 ?
N3 C2 H2 120.1 . . ?
N3 C2 H2 120.1 4_655 . ?
N5 C3 N4 120.0(14) . . ?
N5 C3 H3 120.0 . . ?
N4 C3 H3 120.0 . . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21A I4 0.86 3.15 3.88(9) 143.4 4
N4 H4B I1 0.86 2.89 3.52(6) 131.1 .
N4 H4B I1 0.86 2.89 3.52(6) 131.1 4_655
N3 H3B I6 0.86 2.66 3.272(14) 128.9 6_654

_refine_diff_density_max         2.189
_refine_diff_density_min         -2.722
_refine_diff_density_rms         0.346

####################################################################### 
# 
# 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_P63mc
_database_code_depnum_ccdc_archive 'CCDC 1855908'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H15 Bi2 I9 N6'
_chemical_formula_weight         1695.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           186
_space_group_name_H-M_alt        'P 63 m c'
_space_group_name_Hall           'P 6c -2c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, z+1/2'

_cell_length_a                   8.7119(2)
_cell_length_b                   8.7119(2)
_cell_length_c                   22.0141(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1446.96(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    219.8(4)
_cell_measurement_reflns_used    4165
_cell_measurement_theta_min      2.8970
_cell_measurement_theta_max      25.5570

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.891
_exptl_crystal_F_000             1436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    21.746
_exptl_absorpt_correction_T_min  0.62476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      219.8(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            10697
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.274
_diffrn_reflns_theta_max         25.651
_diffrn_reflns_theta_full        25.651
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1114
_reflns_number_gt                995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

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

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+4.0862P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1114
_refine_ls_number_parameters     43
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_restrained_S_all      1.252
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.014

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 0.3333 0.6667 0.14158(13) 0.0556(8) Uani 1 6 d S T P . .
Bi2 Bi 0.3333 0.6667 0.33116(12) 0.0549(8) Uani 1 6 d S T P . .
I2 I 0.6600(5) 0.8300(2) 0.0675(2) 0.1099(18) Uani 1 2 d S T P . .
I3 I 0.49805(8) 0.50195(8) 0.2354(3) 0.0726(4) Uani 1 2 d S T P . .
I1 I 0.1680(2) 0.3361(4) 0.40195(18) 0.1025(17) Uani 1 2 d S T P . .
C1 C 0.0000 0.0000 0.217(4) 0.18(3) Uiso 1 6 d DS . P . .
H1 H 0.0084 0.0882 0.1911 0.221 Uiso 0.1667 1 calc R U P . .
N2 N 0.071(11) 0.035(6) 0.271(5) 0.18(3) Uiso 0.3333 2 d DS . P . .
H2A H 0.0606 -0.0491 0.2937 0.221 Uiso 0.3333 2 calc R U P . .
H2B H 0.1273 0.1430 0.2835 0.221 Uiso 0.1667 1 calc R U P . .
N3 N -0.0830(10) -0.1661(19) 0.202(4) 0.18(3) Uiso 0.3333 2 d DS . P . .
H3A H -0.0887 -0.2448 0.2265 0.221 Uiso 0.1667 1 calc R U P . .
H3B H -0.1324 -0.1974 0.1665 0.221 Uiso 0.1667 1 calc R U P . .
C6 C 0.6667 0.3333 0.067(2) 0.13(2) Uiso 1 6 d DS . P . .
H6 H 0.6678 0.3339 0.1095 0.152 Uiso 1 6 calc R U P . .
N7 N 0.666(4) 0.4650(18) 0.040(2) 0.13(2) Uiso 0.3333 1 d D . P . .
H7A H 0.6649 0.4682 0.0007 0.152 Uiso 0.3333 1 calc R U P . .
H7B H 0.6665 0.5488 0.0605 0.152 Uiso 0.3333 1 calc R U P . .
C4 C 0.6667 0.3333 0.367(3) 0.20(4) Uiso 1 6 d DS . P . .
H4 H 0.6355 0.3178 0.3257 0.235 Uiso 0.3333 2 calc R U P . .
N5 N 0.679(8) 0.196(4) 0.382(3) 0.20(4) Uiso 0.3333 1 d D . P . .
H5A H 0.7067 0.1862 0.4191 0.235 Uiso 0.3333 1 calc R U P . .
H5B H 0.6587 0.1149 0.3562 0.235 Uiso 0.3333 1 calc R U P . .


_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 I2 2.955(4) 2_665 ?
Bi1 I2 2.955(4) 3_565 ?
Bi1 I2 2.955(4) . ?
Bi1 I3 3.231(5) 2_665 ?
Bi1 I3 3.231(5) 3_565 ?
Bi1 I3 3.231(5) . ?
Bi2 I1 2.941(3) 3_565 ?
Bi2 I1 2.941(3) 2_665 ?
Bi2 I1 2.941(3) . ?
Bi2 I3 3.259(5) 3_565 ?
Bi2 I3 3.259(5) 2_665 ?
Bi2 I3 3.259(5) . ?
C1 N2 1.299(7) . ?
C1 N3 1.298(7) . ?
C1 H1 0.9300 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C6 N7 1.300(7) 9 ?
C6 N7 1.300(7) . ?
C6 H6 0.9300 . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
C4 N5 1.300(7) . ?
C4 N5 1.300(7) 9 ?
C4 H4 0.9300 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?

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
I2 Bi1 I2 92.48(12) 2_665 3_565 ?
I2 Bi1 I2 92.48(12) 2_665 . ?
I2 Bi1 I2 92.48(12) 3_565 . ?
I2 Bi1 I3 91.83(8) 2_665 2_665 ?
I2 Bi1 I3 173.77(15) 3_565 2_665 ?
I2 Bi1 I3 91.82(8) . 2_665 ?
I2 Bi1 I3 91.82(8) 2_665 3_565 ?
I2 Bi1 I3 91.83(8) 3_565 3_565 ?
I2 Bi1 I3 173.77(15) . 3_565 ?
I3 Bi1 I3 83.54(14) 2_665 3_565 ?
I2 Bi1 I3 173.77(15) 2_665 . ?
I2 Bi1 I3 91.82(8) 3_565 . ?
I2 Bi1 I3 91.83(8) . . ?
I3 Bi1 I3 83.54(14) 2_665 . ?
I3 Bi1 I3 83.54(14) 3_565 . ?
I1 Bi2 I1 94.52(12) 3_565 2_665 ?
I1 Bi2 I1 94.52(12) 3_565 . ?
I1 Bi2 I1 94.52(12) 2_665 . ?
I1 Bi2 I3 91.12(9) 3_565 3_565 ?
I1 Bi2 I3 171.69(14) 2_665 3_565 ?
I1 Bi2 I3 91.11(9) . 3_565 ?
I1 Bi2 I3 91.11(9) 3_565 2_665 ?
I1 Bi2 I3 91.12(9) 2_665 2_665 ?
I1 Bi2 I3 171.69(14) . 2_665 ?
I3 Bi2 I3 82.66(15) 3_565 2_665 ?
I1 Bi2 I3 171.69(14) 3_565 . ?
I1 Bi2 I3 91.11(9) 2_665 . ?
I1 Bi2 I3 91.12(9) . . ?
I3 Bi2 I3 82.66(15) 3_565 . ?
I3 Bi2 I3 82.66(15) 2_665 . ?
Bi1 I3 Bi2 80.03(3) . . ?
N2 C1 N3 115.9(9) . . ?
N2 C1 H1 122.1 . . ?
N3 C1 H1 122.1 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N7 C6 N7 124.4(12) 9 . ?
N7 C6 H6 117.8 9 . ?
N7 C6 H6 117.8 . . ?
C6 N7 H7A 120.0 . . ?
C6 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
N5 C4 N5 148(2) . 9 ?
N5 C4 H4 106.1 . . ?
N5 C4 H4 106.1 9 . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A

N2 H2A I1 0.86 2.93 3.70(7) 150.0 3
N3 H3B I2 0.86 2.92 3.69(7) 151.4 1_445
N7 H7B I2 0.86 2.48 3.264(9) 151.3 .
N7 H7A I1 0.86 2.70 3.43(5) 144.5 4_664
C4 H4 I3 0.93 3.14 3.85(5) 134.1 .
C4 H4 I3 0.93 3.14 3.85(5) 134.1 2_655
N5 H5B I3 0.86 2.94 3.64(6) 139.6 2_655

_refine_diff_density_max         0.909
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.116

