# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_bii6-ipyme
_database_code_depnum_ccdc_archive 'CCDC 2234399'
loop_
_audit_author_name
_audit_author_address
'Fangfang Pan'
;Central China Normal University
China
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-03-23 downloaded from the CCDC.
;
_audit_creation_date             2023-01-04
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi I6, 3(C6 H7 I N)'
_chemical_formula_sum            'C18 H21 Bi I9 N3'
_chemical_formula_weight         1630.46
_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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.409(2)
_cell_length_b                   13.542(3)
_cell_length_c                   12.252(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.906(3)
_cell_angle_gamma                90
_cell_volume                     1717.9(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7313
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.445
_cell_measurement_theta_min      2.248
_shelx_estimated_absorpt_T_max   0.351
_shelx_estimated_absorpt_T_min   0.300
_exptl_absorpt_coefficient_mu    13.231
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1759 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.4427.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'orangish orange'
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    3.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1420
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13160
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3214
_reflns_number_total             3528
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       0.00148(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.131
_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)+5.3046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0652
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C12 \\sim C12-C11
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C12) = Uanis(I2)
4. Others
 Fixed Sof: I2(0.5) C8(0.5) H8(0.5) C9(0.5) C10(0.5) H10(0.5) C11(0.5)
 H11(0.5) N2(0.5) C7(0.5) H7(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C7(H7)
5.b Fitted hexagon refined as free rotating group:
 C8(C9,C10,C11,N2,C7)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.500000 1.000000 0.500000 0.03281(10) Uani 1 2 d S . P . .
I3 I 0.78504(4) 0.95277(3) 0.46146(3) 0.04430(12) Uani 1 1 d . . . . .
I4 I 0.48696(5) 1.16223(3) 0.32513(3) 0.04720(13) Uani 1 1 d . . . . .
I5 I 0.60156(5) 1.14982(3) 0.67861(4) 0.05121(14) Uani 1 1 d . . . . .
I1 I 0.80100(4) 0.69073(3) 0.45671(4) 0.04839(13) Uani 1 1 d . . . . .
N1 N 0.8357(5) 0.3355(4) 0.4353(5) 0.0410(12) Uani 1 1 d . . . . .
C1 C 0.8138(7) 0.3894(5) 0.3437(6) 0.0489(16) Uani 1 1 d . . . . .
H1 H 0.804846 0.357938 0.275863 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8043(7) 0.4894(5) 0.3482(6) 0.0463(15) Uani 1 1 d . . . . .
H2 H 0.788923 0.525890 0.283858 0.056 Uiso 1 1 calc R U . . .
C3 C 0.8177(5) 0.5365(4) 0.4488(5) 0.0371(13) Uani 1 1 d . . . . .
C4 C 0.8411(6) 0.4803(5) 0.5427(6) 0.0430(14) Uani 1 1 d . . . . .
H4 H 0.851889 0.510629 0.611186 0.052 Uiso 1 1 calc R U . . .
C5 C 0.8482(6) 0.3794(5) 0.5344(6) 0.0461(15) Uani 1 1 d . . . . .
H5 H 0.861659 0.341170 0.597607 0.055 Uiso 1 1 calc R U . . .
C6 C 0.8489(8) 0.2263(5) 0.4298(7) 0.061(2) Uani 1 1 d . . . . .
H6A H 0.778670 0.199627 0.381804 0.091 Uiso 1 1 calc R U . . .
H6B H 0.847242 0.198774 0.501870 0.091 Uiso 1 1 calc R U . . .
H6C H 0.929247 0.209890 0.402183 0.091 Uiso 1 1 calc R U . . .
I2 I 0.9212(4) 0.95686(11) 0.7475(2) 0.0547(4) Uani 0.5 1 d . . P A -1
C8 C 0.9987(11) 1.0775(9) 0.9477(7) 0.040(4) Uani 0.5 1 d G U P A -1
H8 H 0.989229 1.128884 0.897154 0.048 Uiso 0.5 1 calc R U P A -1
C9 C 0.9781(11) 0.9806(10) 0.9129(5) 0.035(3) Uani 0.5 1 d G . P A -1
C10 C 0.9923(11) 0.9037(8) 0.9884(7) 0.041(4) Uani 0.5 1 d G . P A -1
H10 H 0.978432 0.838894 0.965104 0.049 Uiso 0.5 1 calc R U P A -1
C11 C 1.0271(11) 0.9238(7) 1.0987(6) 0.043(4) Uani 0.5 1 d DG . P A -1
H11 H 1.036649 0.872445 1.149242 0.051 Uiso 0.5 1 calc R U P A -1
N2 N 1.0478(10) 1.0208(8) 1.1335(6) 0.038(3) Uani 0.5 1 d G . P A -1
C7 C 1.0336(10) 1.0976(7) 1.0580(8) 0.042(4) Uani 0.5 1 d DG . P A -1
H7 H 1.047447 1.162436 1.081296 0.050 Uiso 0.5 1 calc R U P A -1
C12 C 1.076(6) 1.0400(15) 1.240(4) 0.0547(4) Uani 0.5 1 d D U P A -1
H12A H 1.069930 0.980353 1.281340 0.082 Uiso 0.5 1 calc R U P A -1
H12B H 1.016289 1.087873 1.262734 0.082 Uiso 0.5 1 calc R U P A -1
H12C H 1.162307 1.065664 1.252179 0.082 Uiso 0.5 1 calc R U P A -1


_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 I3 3.1181(7) 3_676 ?
Bi1 I3 3.1181(7) . ?
Bi1 I4 3.0620(6) . ?
Bi1 I4 3.0620(6) 3_676 ?
Bi1 I5 3.0898(6) . ?
Bi1 I5 3.0898(6) 3_676 ?
I1 C3 2.099(6) . ?
N1 C1 1.339(9) . ?
N1 C5 1.347(8) . ?
N1 C6 1.487(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.359(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(9) . ?
C3 C4 1.380(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(9) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
I2 C9 2.077(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C8 C7 1.3900 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 N2 1.3900 . ?
N2 C7 1.3900 . ?
N2 C12 1.33(5) . ?
C7 H7 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
I3 Bi1 I3 180.0 . 3_676 ?
I4 Bi1 I3 90.890(13) 3_676 3_676 ?
I4 Bi1 I3 90.891(13) . . ?
I4 Bi1 I3 89.110(13) . 3_676 ?
I4 Bi1 I3 89.109(13) 3_676 . ?
I4 Bi1 I4 180.000(18) . 3_676 ?
I4 Bi1 I5 89.326(19) 3_676 . ?
I4 Bi1 I5 89.326(19) . 3_676 ?
I4 Bi1 I5 90.674(19) . . ?
I4 Bi1 I5 90.675(19) 3_676 3_676 ?
I5 Bi1 I3 88.879(15) 3_676 3_676 ?
I5 Bi1 I3 88.879(15) . . ?
I5 Bi1 I3 91.121(15) . 3_676 ?
I5 Bi1 I3 91.121(14) 3_676 . ?
I5 Bi1 I5 179.999(18) . 3_676 ?
C1 N1 C5 120.5(6) . . ?
C1 N1 C6 120.9(6) . . ?
C5 N1 C6 118.7(6) . . ?
N1 C1 H1 119.4 . . ?
N1 C1 C2 121.1(6) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(7) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 I1 120.0(5) . . ?
C4 C3 I1 121.2(5) . . ?
C4 C3 C2 118.8(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.4(6) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 I2 117.7(6) . . ?
C10 C9 I2 122.3(6) . . ?
C10 C9 C8 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
N2 C11 C10 120.0 . . ?
N2 C11 H11 120.0 . . ?
C7 N2 C11 120.0 . . ?
C12 N2 C11 119.8(4) . . ?
C12 N2 C7 120.2(4) . . ?
C8 C7 H7 120.0 . . ?
N2 C7 C8 120.0 . . ?
N2 C7 H7 120.0 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
I1 C3 C4 C5 178.4(5) . . . . ?
N1 C1 C2 C3 0.1(10) . . . . ?
C1 N1 C5 C4 -1.3(9) . . . . ?
C1 C2 C3 I1 -179.2(5) . . . . ?
C1 C2 C3 C4 0.3(10) . . . . ?
C2 C3 C4 C5 -1.1(9) . . . . ?
C3 C4 C5 N1 1.6(10) . . . . ?
C5 N1 C1 C2 0.4(10) . . . . ?
C6 N1 C1 C2 -178.6(6) . . . . ?
C6 N1 C5 C4 177.8(6) . . . . ?
I2 C9 C10 C11 -178.2(6) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C8 C7 N2 0.0 . . . . ?
C9 C10 C11 N2 0.0 . . . . ?
C10 C11 N2 C7 0.0 . . . . ?
C10 C11 N2 C12 177(3) . . . . ?
C11 N2 C7 C8 0.0 . . . . ?
C7 C8 C9 I2 178.3(6) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C12 N2 C7 C8 -177(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       thermochromism
####################################################################### 
# 
# 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_bii4_ipyme
_database_code_depnum_ccdc_archive 'CCDC 2234400'
loop_
_audit_author_name
_audit_author_address
'Fangfang Pan'
;Central China Normal University
China
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-03-23 downloaded from the CCDC.
;
_audit_creation_date             2023-01-05
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I8, 2(C6 H7 I N), 0.5(C H4 O)'
_chemical_formula_sum            'C12.50 H16 Bi2 I10 N2 O0.50'
_chemical_formula_weight         1889.23
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7329(16)
_cell_length_b                   10.364(2)
_cell_length_c                   11.706(2)
_cell_angle_alpha                70.549(3)
_cell_angle_beta                 81.104(3)
_cell_angle_gamma                88.664(3)
_cell_volume                     873.6(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3379
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.656
_cell_measurement_theta_min      2.289
_shelx_estimated_absorpt_T_max   0.313
_shelx_estimated_absorpt_T_min   0.132
_exptl_absorpt_coefficient_mu    18.900
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.4447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0403 after correction.
The Ratio of minimum to maximum transmission is 0.5958.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'orangish brown'
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    3.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             805
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9836
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.369
_diffrn_reflns_theta_min         1.868
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.900
_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                4266
_reflns_number_total             5648
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.805
_refine_diff_density_min         -1.424
_refine_diff_density_rms         0.264
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         5648
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      0.997
_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)+(0.0546P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: O1(0.25) H1(0.25) C7(0.25) H7A(0.25) H7B(0.25) H7C(0.25)
4.a Riding coordinates:
 O1(H1), C7(H7A,H7B,H7C)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
4.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.27494(3) 0.93826(3) 0.92108(2) 0.02893(8) Uani 1 1 d . . . . .
I1 I 0.13056(8) 0.67190(6) 0.93820(6) 0.05004(15) Uani 1 1 d . . . . .
I2 I -0.03675(7) 1.09802(6) 0.81211(4) 0.04321(14) Uani 1 1 d . . . . .
I3 I 0.57647(7) 0.78384(5) 1.05049(5) 0.04130(13) Uani 1 1 d . . . . .
I4 I 0.47166(9) 1.00120(7) 0.67278(5) 0.05519(18) Uani 1 1 d . . . . .
I1O I 0.21802(9) 0.56749(8) 0.67134(7) 0.06108(18) Uani 1 1 d . . . . .
N1 N 0.2878(9) 0.4124(7) 0.3216(7) 0.0434(15) Uani 1 1 d . . . . .
C1 C 0.2507(11) 0.5016(8) 0.5188(8) 0.0431(18) Uani 1 1 d . . . . .
C2 C 0.2385(14) 0.5920(9) 0.4050(9) 0.054(2) Uani 1 1 d . . . . .
H2 H 0.214989 0.699014 0.392015 0.065 Uiso 1 1 calc R U . . .
C3 C 0.2569(13) 0.5443(9) 0.3060(9) 0.055(2) Uani 1 1 d . . . . .
H3 H 0.245996 0.614597 0.215386 0.066 Uiso 1 1 calc R U . . .
C4 C 0.3027(13) 0.3219(9) 0.4318(9) 0.053(2) Uani 1 1 d . . . . .
H4 H 0.330284 0.216260 0.441303 0.064 Uiso 1 1 calc R U . . .
C5 C 0.2829(12) 0.3634(9) 0.5330(9) 0.050(2) Uani 1 1 d . . . . .
H5 H 0.291982 0.290350 0.622759 0.060 Uiso 1 1 calc R U . . .
C6 C 0.3066(15) 0.3658(12) 0.2115(11) 0.069(3) Uani 1 1 d . . . . .
H6A H 0.180138 0.351524 0.191358 0.103 Uiso 1 1 calc R U . . .
H6B H 0.373326 0.271580 0.230629 0.103 Uiso 1 1 calc R U . . .
H6C H 0.379833 0.441377 0.134727 0.103 Uiso 1 1 calc R U . . .
O1 O 0.018(6) -0.033(4) 0.517(4) 0.070(10) Uani 0.25 1 d . U P A -1
H1 H 0.009449 -0.094736 0.488639 0.106 Uiso 0.25 1 d R U P A -1
C7 C 0.044(6) 0.093(4) 0.421(4) 0.066(11) Uani 0.25 1 d . U P A -1
H7A H -0.045018 0.110925 0.369619 0.098 Uiso 0.25 1 d R U P A -1
H7B H 0.155912 0.091095 0.373109 0.098 Uiso 0.25 1 d R U P A -1
H7C H 0.046262 0.164215 0.456679 0.098 Uiso 0.25 1 d R U P A -1


_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 2.9349(8) . ?
Bi1 I2 3.2802(8) 2_577 ?
Bi1 I2 3.0881(7) . ?
Bi1 I3 3.0979(7) . ?
Bi1 I3 3.2614(8) 2_677 ?
Bi1 I4 2.9333(8) . ?
I1O C1 2.094(9) . ?
N1 C3 1.339(11) . ?
N1 C4 1.339(11) . ?
N1 C6 1.506(14) . ?
C1 C2 1.366(12) . ?
C1 C5 1.406(12) . ?
C2 H2 1.0830 . ?
C2 C3 1.391(14) . ?
C3 H3 1.0830 . ?
C4 H4 1.0830 . ?
C4 C5 1.375(14) . ?
C5 H5 1.0830 . ?
C6 H6A 1.0661 . ?
C6 H6B 1.0660 . ?
C6 H6C 1.0660 . ?
O1 H1 0.8200 . ?
O1 C7 1.40(6) . ?
C7 H7A 0.9599 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9601 . ?

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 I2 93.76(2) . . ?
I1 Bi1 I2 87.879(19) . 2_577 ?
I1 Bi1 I3 87.97(2) . . ?
I1 Bi1 I3 170.897(19) . 2_677 ?
I2 Bi1 I2 85.108(19) . 2_577 ?
I2 Bi1 I3 175.125(17) . . ?
I2 Bi1 I3 89.62(2) . 2_677 ?
I3 Bi1 I2 90.41(2) . 2_577 ?
I3 Bi1 I2 83.990(19) 2_677 2_577 ?
I3 Bi1 I3 88.000(18) . 2_677 ?
I4 Bi1 I1 96.21(2) . . ?
I4 Bi1 I2 173.600(17) . 2_577 ?
I4 Bi1 I2 89.70(2) . . ?
I4 Bi1 I3 92.25(2) . 2_677 ?
I4 Bi1 I3 94.64(2) . . ?
Bi1 I2 Bi1 94.892(19) . 2_577 ?
Bi1 I3 Bi1 92.000(19) . 2_677 ?
C3 N1 C4 121.8(9) . . ?
C3 N1 C6 118.6(8) . . ?
C4 N1 C6 119.6(8) . . ?
C2 C1 I1O 120.3(7) . . ?
C2 C1 C5 119.5(9) . . ?
C5 C1 I1O 120.2(6) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(8) . . ?
C3 C2 H2 120.6 . . ?
N1 C3 C2 120.6(8) . . ?
N1 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
N1 C4 H4 120.1 . . ?
N1 C4 C5 119.9(8) . . ?
C5 C4 H4 120.1 . . ?
C1 C5 H5 120.3 . . ?
C4 C5 C1 119.4(8) . . ?
C4 C5 H5 120.3 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 O1 H1 109.7 . . ?
O1 C7 H7A 113.1 . . ?
O1 C7 H7B 107.1 . . ?
O1 C7 H7C 108.2 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
I1O C1 C2 C3 -178.5(7) . . . . ?
I1O C1 C5 C4 179.5(7) . . . . ?
N1 C4 C5 C1 -1.3(15) . . . . ?
C1 C2 C3 N1 -0.7(16) . . . . ?
C2 C1 C5 C4 0.4(15) . . . . ?
C3 N1 C4 C5 1.2(15) . . . . ?
C4 N1 C3 C2 -0.2(15) . . . . ?
C5 C1 C2 C3 0.6(15) . . . . ?
C6 N1 C3 C2 -180.0(9) . . . . ?
C6 N1 C4 C5 -179.0(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       thermochromism
####################################################################### 
# 
# 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_bi2i9_ipyme
_database_code_depnum_ccdc_archive 'CCDC 2234401'
loop_
_audit_author_name
_audit_author_address
'Fangfang Pan'
;Central China Normal University
China
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-03-23 downloaded from the CCDC.
;
_audit_creation_date             2022-12-30
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, 3(C6 H7 I N)'
_chemical_formula_sum            'C18 H21 Bi2 I12 N3'
_chemical_formula_weight         2220.14
_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'

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

_cell_length_a                   10.6214(19)
_cell_length_b                   12.362(2)
_cell_length_c                   16.562(3)
_cell_angle_alpha                79.662(3)
_cell_angle_beta                 84.417(3)
_cell_angle_gamma                89.782(3)
_cell_volume                     2129.0(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4155
_cell_measurement_temperature    296.15(10)
_cell_measurement_theta_max      24.91
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.969
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.4988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1177 before and 0.0386 after correction.
The Ratio of minimum to maximum transmission is 0.6684.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    3.463
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23307
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.691
_diffrn_reflns_theta_min         1.256
_diffrn_ambient_temperature      296.15(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           45.0
_diffrn_source_power             2.25
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6792
_reflns_number_total             13292
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.204
_refine_diff_density_min         -1.748
_refine_diff_density_rms         0.187
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         13292
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      0.959
_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)+(0.0331P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7A-C8A = C7A-C11A = C8B-C7B = C11B-C7B
 1.39 with sigma of 0.01
 N3B-C9B = N3B-C10B = N2-C10A = N2-C9A
 1.35 with sigma of 0.01
 C8B-C9B = C10A-C11A = C11B-C10B = C9A-C8A
 1.38 with sigma of 0.01
 C12B-N3B
 1.46 with sigma of 0.01
 N2-C12A
 1.46 with sigma of 0.01
 C9B-C12B \\sim C12B-C10B
 with sigma of 0.01
 C11A-C9A \\sim C8A-C10A \\sim C9B-C11B \\sim C8B-C10B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(N3B) \\sim Ueq, Uanis(C7B) \\sim Ueq, Uanis(C8B) \\sim Ueq, Uanis(C11B)
\\sim Ueq, Uanis(C9B) \\sim Ueq, Uanis(C10B) \\sim Ueq, Uanis(C12B) \\sim Ueq,
Uanis(C12A) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C7A)
\\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(C10A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C12A) = Uanis(I2OB)
Uanis(I2OA) = Uanis(C12B)
4. Others
 Sof(I2OB)=Sof(N3B)=Sof(C7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=
 Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(I2OA)=Sof(N2)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C8B(H8B), C9B(H9B), C10B(H10B),
 C11B(H11B)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C18(H18A,H18B,H18C), C12A(H12A,H12B,H12C), C12B(H12D,H12E,
 H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.43730(3) 0.83555(3) 0.77024(2) 0.04609(9) Uani 1 1 d . . . . .
Bi2 Bi 0.18086(3) 0.58923(3) 0.74556(2) 0.04424(9) Uani 1 1 d . . . . .
I1 I 0.47315(9) 1.04729(6) 0.65162(5) 0.0933(3) Uani 1 1 d . . . . .
I2 I 0.71160(6) 0.79220(6) 0.76869(4) 0.06312(18) Uani 1 1 d . . . . .
I3 I 0.43310(7) 0.94229(6) 0.91447(4) 0.0729(2) Uani 1 1 d . . . . .
I4 I 0.41433(5) 0.70991(5) 0.61560(4) 0.04889(14) Uani 1 1 d . . . . .
I5 I 0.13215(6) 0.83990(5) 0.77250(4) 0.05932(17) Uani 1 1 d . . . . .
I6 I 0.37515(7) 0.60016(5) 0.88379(4) 0.06492(18) Uani 1 1 d . . . . .
I7 I 0.01395(6) 0.61059(5) 0.61104(4) 0.05999(17) Uani 1 1 d . . . . .
I8 I 0.27622(7) 0.37274(5) 0.71935(5) 0.06883(19) Uani 1 1 d . . . . .
I9 I -0.02451(7) 0.49737(6) 0.86962(4) 0.0736(2) Uani 1 1 d . . . . .
I1O I 0.82798(7) 1.02429(6) 0.86866(5) 0.0739(2) Uani 1 1 d . . . . .
N1 N 1.1384(8) 1.2332(6) 0.9689(5) 0.058(2) Uani 1 1 d . . . . .
C1 C 0.9611(9) 1.1144(7) 0.9137(5) 0.053(2) Uani 1 1 d . . . . .
C2 C 1.0859(10) 1.1142(8) 0.8815(7) 0.066(3) Uani 1 1 d . . . . .
H2 H 1.110345 1.072690 0.841180 0.080 Uiso 1 1 calc R U . . .
C3 C 1.1728(10) 1.1753(8) 0.9095(7) 0.066(3) Uani 1 1 d . . . . .
H3 H 1.256749 1.176851 0.887249 0.079 Uiso 1 1 calc R U . . .
C4 C 1.0208(10) 1.2333(8) 1.0018(6) 0.064(3) Uani 1 1 d . . . . .
H4 H 0.999263 1.273501 1.043384 0.077 Uiso 1 1 calc R U . . .
C5 C 0.9301(10) 1.1742(8) 0.9749(6) 0.064(3) Uani 1 1 d . . . . .
H5 H 0.846826 1.174574 0.998135 0.077 Uiso 1 1 calc R U . . .
C6 C 1.2357(12) 1.2996(10) 0.9967(8) 0.091(4) Uani 1 1 d . . . . .
H6A H 1.276269 1.349004 0.950126 0.137 Uiso 1 1 calc R U . . .
H6B H 1.297587 1.251790 1.022245 0.137 Uiso 1 1 calc R U . . .
H6C H 1.196444 1.341152 1.035772 0.137 Uiso 1 1 calc R U . . .
I3O I -0.02110(9) 0.26539(7) 0.63835(5) 0.0918(3) Uani 1 1 d . . . . .
N3 N -0.1883(7) -0.0438(7) 0.5433(5) 0.058(2) Uani 1 1 d . . . . .
C13 C -0.0932(9) 0.1338(9) 0.5963(6) 0.061(3) Uani 1 1 d . . . . .
C14 C -0.0522(10) 0.0296(9) 0.6233(6) 0.068(3) Uani 1 1 d . . . . .
H14 H 0.009242 0.018387 0.660151 0.081 Uiso 1 1 calc R U . . .
C15 C -0.1009(9) -0.0575(8) 0.5964(6) 0.063(3) Uani 1 1 d . . . . .
H15 H -0.072557 -0.127877 0.615439 0.075 Uiso 1 1 calc R U . . .
C16 C -0.2303(9) 0.0566(8) 0.5127(6) 0.059(2) Uani 1 1 d . . . . .
H16 H -0.291111 0.064930 0.475333 0.071 Uiso 1 1 calc R U . . .
C17 C -0.1821(9) 0.1456(8) 0.5374(6) 0.062(3) Uani 1 1 d . . . . .
H17 H -0.208157 0.215573 0.515025 0.075 Uiso 1 1 calc R U . . .
C18 C -0.2483(11) -0.1405(9) 0.5186(8) 0.084(3) Uani 1 1 d . . . . .
H18A H -0.324525 -0.161479 0.554058 0.127 Uiso 1 1 calc R U . . .
H18B H -0.190769 -0.200914 0.523361 0.127 Uiso 1 1 calc R U . . .
H18C H -0.268151 -0.121302 0.462552 0.127 Uiso 1 1 calc R U . . .
I2OA I 0.3986(4) 0.71035(19) 1.10591(15) 0.1069(8) Uani 0.505(2) 1 d . . P A 1
N2 N 0.339(2) 0.5245(13) 1.3927(10) 0.049(5) Uani 0.505(2) 1 d D U P A 1
C7A C 0.373(3) 0.6312(15) 1.2285(11) 0.046(5) Uani 0.505(2) 1 d D U P A 1
C8A C 0.390(2) 0.6843(14) 1.2941(10) 0.054(5) Uani 0.505(2) 1 d D U P A 1
H8A H 0.414590 0.758138 1.282852 0.064 Uiso 0.505(2) 1 calc R U P A 1
C9A C 0.373(2) 0.6312(14) 1.3752(10) 0.058(6) Uani 0.505(2) 1 d D U P A 1
H9A H 0.385606 0.669200 1.417566 0.070 Uiso 0.505(2) 1 calc R U P A 1
C10A C 0.320(4) 0.4685(16) 1.3323(11) 0.066(8) Uani 0.505(2) 1 d D U P A 1
H10A H 0.298453 0.394060 1.345068 0.079 Uiso 0.505(2) 1 calc R U P A 1
C11A C 0.332(3) 0.5220(15) 1.2516(11) 0.056(7) Uani 0.505(2) 1 d D U P A 1
H11A H 0.312914 0.483818 1.210846 0.068 Uiso 0.505(2) 1 calc R U P A 1
C12A C 0.311(6) 0.471(5) 1.4788(15) 0.0775(6) Uani 0.505(2) 1 d D U P A 1
H12A H 0.245714 0.510036 1.504983 0.116 Uiso 0.505(2) 1 calc R U P A 1
H12B H 0.386237 0.471185 1.506874 0.116 Uiso 0.505(2) 1 calc R U P A 1
H12C H 0.283924 0.396468 1.481019 0.116 Uiso 0.505(2) 1 calc R U P A 1
I2OB I 0.3068(4) 0.4762(3) 1.49105(12) 0.0775(6) Uani 0.495(2) 1 d . . P A 2
N3B N 0.374(2) 0.6370(14) 1.1968(11) 0.064(6) Uani 0.495(2) 1 d D U P A 2
C7B C 0.335(2) 0.5530(14) 1.3653(11) 0.039(5) Uani 0.495(2) 1 d D U P A 2
C8B C 0.321(3) 0.4835(14) 1.3095(10) 0.044(5) Uani 0.495(2) 1 d D U P A 2
H8B H 0.297361 0.409835 1.326383 0.053 Uiso 0.495(2) 1 calc R U P A 2
C9B C 0.343(3) 0.5304(15) 1.2277(10) 0.052(6) Uani 0.495(2) 1 d D U P A 2
H9B H 0.336949 0.484249 1.189651 0.063 Uiso 0.495(2) 1 calc R U P A 2
C10B C 0.387(2) 0.6981(15) 1.2550(9) 0.062(6) Uani 0.495(2) 1 d D U P A 2
H10B H 0.407289 0.772240 1.236727 0.074 Uiso 0.495(2) 1 calc R U P A 2
C11B C 0.374(2) 0.6613(14) 1.3397(9) 0.052(5) Uani 0.495(2) 1 d D U P A 2
H11B H 0.391178 0.706472 1.376812 0.062 Uiso 0.495(2) 1 calc R U P A 2
C12B C 0.384(6) 0.681(2) 1.1079(13) 0.1069(8) Uani 0.495(2) 1 d D U P A 2
H12D H 0.344085 0.751346 1.098506 0.160 Uiso 0.495(2) 1 calc R U P A 2
H12E H 0.343717 0.631351 1.080013 0.160 Uiso 0.495(2) 1 calc R U P A 2
H12F H 0.471981 0.689580 1.087163 0.160 Uiso 0.495(2) 1 calc R U P A 2


_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 2.9787(9) . ?
Bi1 I2 2.9588(9) . ?
Bi1 I3 2.9257(8) . ?
Bi1 I4 3.2533(8) . ?
Bi1 I5 3.2380(9) . ?
Bi1 I6 3.2014(8) . ?
Bi2 I4 3.2933(8) . ?
Bi2 I5 3.2417(9) . ?
Bi2 I6 3.2481(8) . ?
Bi2 I7 2.9547(8) . ?
Bi2 I8 2.9475(9) . ?
Bi2 I9 2.9289(8) . ?
I1O C1 2.077(9) . ?
N1 C3 1.339(13) . ?
N1 C4 1.314(12) . ?
N1 C6 1.480(13) . ?
C1 C2 1.380(13) . ?
C1 C5 1.373(13) . ?
C2 H2 0.9300 . ?
C2 C3 1.361(14) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.365(14) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
I3O C13 2.059(10) . ?
N3 C15 1.329(12) . ?
N3 C16 1.346(12) . ?
N3 C18 1.496(13) . ?
C13 C14 1.370(14) . ?
C13 C17 1.411(13) . ?
C14 H14 0.9300 . ?
C14 C15 1.358(14) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.358(13) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
I2OA C7A 2.083(18) . ?
N2 C9A 1.344(9) . ?
N2 C10A 1.345(9) . ?
N2 C12A 1.462(10) . ?
C7A C8A 1.394(10) . ?
C7A C11A 1.393(10) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.380(9) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9300 . ?
C10A C11A 1.375(10) . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
I2OB C7B 2.121(18) . ?
N3B C9B 1.354(9) . ?
N3B C10B 1.345(9) . ?
N3B C12B 1.469(10) . ?
C7B C8B 1.389(9) . ?
C7B C11B 1.384(10) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.372(10) . ?
C9B H9B 0.9300 . ?
C10B H10B 0.9300 . ?
C10B C11B 1.389(9) . ?
C11B H11B 0.9300 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 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
I1 Bi1 I4 89.02(3) . . ?
I1 Bi1 I5 93.45(2) . . ?
I1 Bi1 I6 173.18(2) . . ?
I2 Bi1 I1 93.87(3) . . ?
I2 Bi1 I4 91.794(19) . . ?
I2 Bi1 I5 170.54(2) . . ?
I2 Bi1 I6 90.46(2) . . ?
I3 Bi1 I1 93.29(3) . . ?
I3 Bi1 I2 92.93(2) . . ?
I3 Bi1 I4 174.59(2) . . ?
I3 Bi1 I5 92.62(2) . . ?
I3 Bi1 I6 91.74(3) . . ?
I5 Bi1 I4 82.353(17) . . ?
I6 Bi1 I4 85.57(2) . . ?
I6 Bi1 I5 81.72(2) . . ?
I5 Bi2 I4 81.682(19) . . ?
I5 Bi2 I6 80.957(19) . . ?
I6 Bi2 I4 84.18(2) . . ?
I7 Bi2 I4 90.46(2) . . ?
I7 Bi2 I5 92.77(2) . . ?
I7 Bi2 I6 172.26(2) . . ?
I8 Bi2 I4 89.79(2) . . ?
I8 Bi2 I5 169.14(2) . . ?
I8 Bi2 I6 91.54(2) . . ?
I8 Bi2 I7 94.03(2) . . ?
I9 Bi2 I4 174.93(2) . . ?
I9 Bi2 I5 93.89(2) . . ?
I9 Bi2 I6 92.72(3) . . ?
I9 Bi2 I7 92.22(3) . . ?
I9 Bi2 I8 94.31(2) . . ?
Bi1 I4 Bi2 79.663(18) . . ?
Bi1 I5 Bi2 80.655(16) . . ?
Bi1 I6 Bi2 81.109(19) . . ?
C3 N1 C6 118.7(10) . . ?
C4 N1 C3 121.6(9) . . ?
C4 N1 C6 119.7(9) . . ?
C2 C1 I1O 119.1(7) . . ?
C5 C1 I1O 122.6(7) . . ?
C5 C1 C2 118.3(9) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(10) . . ?
C3 C2 H2 120.4 . . ?
N1 C3 C2 120.5(10) . . ?
N1 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
N1 C4 H4 120.1 . . ?
N1 C4 C5 119.9(10) . . ?
C5 C4 H4 120.1 . . ?
C1 C5 H5 119.8 . . ?
C4 C5 C1 120.4(10) . . ?
C4 C5 H5 119.8 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C15 N3 C16 121.7(9) . . ?
C15 N3 C18 120.9(9) . . ?
C16 N3 C18 117.4(9) . . ?
C14 C13 I3O 120.2(8) . . ?
C14 C13 C17 116.9(10) . . ?
C17 C13 I3O 122.8(8) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(10) . . ?
C15 C14 H14 119.8 . . ?
N3 C15 C14 121.1(10) . . ?
N3 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
N3 C16 H16 120.7 . . ?
N3 C16 C17 118.7(9) . . ?
C17 C16 H16 120.7 . . ?
C13 C17 H17 119.4 . . ?
C16 C17 C13 121.2(9) . . ?
C16 C17 H17 119.4 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9A N2 C10A 121.0(18) . . ?
C9A N2 C12A 119(3) . . ?
C10A N2 C12A 119(3) . . ?
C8A C7A I2OA 122.7(11) . . ?
C11A C7A I2OA 122.6(12) . . ?
C11A C7A C8A 114.6(16) . . ?
C7A C8A H8A 118.8 . . ?
C9A C8A C7A 122.4(15) . . ?
C9A C8A H8A 118.8 . . ?
N2 C9A C8A 119.7(16) . . ?
N2 C9A H9A 120.2 . . ?
C8A C9A H9A 120.2 . . ?
N2 C10A H10A 120.3 . . ?
N2 C10A C11A 119.5(16) . . ?
C11A C10A H10A 120.3 . . ?
C7A C11A H11A 118.7 . . ?
C10A C11A C7A 122.7(15) . . ?
C10A C11A H11A 118.7 . . ?
N2 C12A H12A 109.5 . . ?
N2 C12A H12B 109.5 . . ?
N2 C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C9B N3B C12B 122.2(11) . . ?
C10B N3B C9B 113.7(18) . . ?
C10B N3B C12B 124.0(11) . . ?
C8B C7B I2OB 114.7(12) . . ?
C11B C7B I2OB 123.3(11) . . ?
C11B C7B C8B 121.8(17) . . ?
C7B C8B H8B 122.1 . . ?
C9B C8B C7B 115.7(15) . . ?
C9B C8B H8B 122.1 . . ?
N3B C9B C8B 126.7(16) . . ?
N3B C9B H9B 116.7 . . ?
C8B C9B H9B 116.7 . . ?
N3B C10B H10B 116.8 . . ?
N3B C10B C11B 126.3(16) . . ?
C11B C10B H10B 116.8 . . ?
C7B C11B C10B 115.5(15) . . ?
C7B C11B H11B 122.2 . . ?
C10B C11B H11B 122.2 . . ?
N3B C12B H12D 109.5 . . ?
N3B C12B H12E 109.5 . . ?
N3B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 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
I1O C1 C2 C3 178.4(8) . . . . ?
I1O C1 C5 C4 -179.2(7) . . . . ?
N1 C4 C5 C1 0.2(15) . . . . ?
C1 C2 C3 N1 1.5(15) . . . . ?
C2 C1 C5 C4 1.1(15) . . . . ?
C3 N1 C4 C5 -0.7(15) . . . . ?
C4 N1 C3 C2 -0.1(14) . . . . ?
C5 C1 C2 C3 -1.9(15) . . . . ?
C6 N1 C3 C2 -179.2(10) . . . . ?
C6 N1 C4 C5 178.4(10) . . . . ?
I3O C13 C14 C15 179.1(8) . . . . ?
I3O C13 C17 C16 -178.2(8) . . . . ?
N3 C16 C17 C13 -2.3(14) . . . . ?
C13 C14 C15 N3 0.4(15) . . . . ?
C14 C13 C17 C16 4.0(14) . . . . ?
C15 N3 C16 C17 -0.4(14) . . . . ?
C16 N3 C15 C14 1.4(14) . . . . ?
C17 C13 C14 C15 -2.9(15) . . . . ?
C18 N3 C15 C14 -175.6(10) . . . . ?
C18 N3 C16 C17 176.7(9) . . . . ?
I2OA C7A C8A C9A -180(2) . . . . ?
I2OA C7A C11A C10A 177(3) . . . . ?
N2 C10A C11A C7A 5(6) . . . . ?
C7A C8A C9A N2 0(4) . . . . ?
C8A C7A C11A C10A -5(5) . . . . ?
C9A N2 C10A C11A -2(5) . . . . ?
C10A N2 C9A C8A -1(4) . . . . ?
C11A C7A C8A C9A 2(4) . . . . ?
C12A N2 C9A C8A -175(4) . . . . ?
C12A N2 C10A C11A 173(4) . . . . ?
I2OB C7B C8B C9B -178(2) . . . . ?
I2OB C7B C11B C10B -179.8(19) . . . . ?
N3B C10B C11B C7B -5(4) . . . . ?
C7B C8B C9B N3B -2(5) . . . . ?
C8B C7B C11B C10B 6(4) . . . . ?
C9B N3B C10B C11B 1(4) . . . . ?
C10B N3B C9B C8B 3(5) . . . . ?
C11B C7B C8B C9B -3(4) . . . . ?
C12B N3B C9B C8B -174(4) . . . . ?
C12B N3B C10B C11B 178(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       thermochromism
