# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_DMEDABiI-Red
_database_code_depnum_ccdc_archive 'CCDC 1905325'
loop_
_audit_author_name
_audit_author_address
'Jiangwei Zhang'
;Dalian Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C4 H14 N2), 2(Bi I6)'
_chemical_formula_sum            'C12 H42 Bi2 I12 N6'
_chemical_formula_weight         2211.28
_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 0.0181 0.0091 '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 -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   14.6871(3)
_cell_length_b                   14.6871(3)
_cell_length_c                   36.1205(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6747.7(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    3884
_cell_measurement_temperature    297(1)
_cell_measurement_theta_max      73.2540
_cell_measurement_theta_min      5.9960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    79.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    3.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             5748.0
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            5615
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.556
_diffrn_reflns_theta_min         4.251
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    126.00 168.00   0.50   13.00    --   94.60  66.00 151.00   84
  2  ω    -27.00  30.00   0.50    5.00    --    0.00 -82.00-120.00  114
  3  ω     87.00 166.00   0.50   13.00    --   94.60  82.00-120.00  158
  4  ω     12.00  38.00   0.50    5.00    --    0.00  32.00  11.00   52
  5  ω      5.00  31.00   0.50    5.00    --    0.00 -82.00 -90.00   52
  6  ω     78.00 115.00   0.50   13.00    --   94.60 -82.00   0.00   74
  7  ω     87.00 143.00   0.50   13.00    --   94.60  82.00   0.00  112
  8  ω     36.00  63.00   0.50   13.00    --   94.60 -82.00   0.00   54
  9  ω    143.00 176.00   0.50   13.00    --   94.60  82.00 -90.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1006818000
_diffrn_orient_matrix_UB_12      -0.0056566000
_diffrn_orient_matrix_UB_13      0.0067934000
_diffrn_orient_matrix_UB_21      -0.0540554000
_diffrn_orient_matrix_UB_22      -0.1118220000
_diffrn_orient_matrix_UB_23      -0.0164168000
_diffrn_orient_matrix_UB_31      0.0403724667
_diffrn_orient_matrix_UB_32      0.0462761333
_diffrn_orient_matrix_UB_33      -0.0387525667
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1372
_reflns_number_total             1494
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.587
_refine_diff_density_min         -4.855
_refine_diff_density_rms         0.616
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         1494
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1075P)²+201.4569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1A-C1A_$1
 1.53 with sigma of 0.02
 N1-C1B
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C1B) = Uanis(C1A)
4. Others
 Sof(H1BD)=Sof(H1BC)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=1-FVAR(1)
 Sof(H1AB)=Sof(H1AA)=Sof(C1A)=Sof(H1AC)=Sof(H1AD)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 N1(H1AB,H1AA), N1(H1BD,H1BC), C1A(H1AC,H1AD), C1B(H1BA,H1BB)
5.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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 0.666667 0.333333 0.69708(2) 0.0145(3) Uani 1 3 d S T P . .
I2 I 0.64727(6) 0.49580(6) 0.74004(2) 0.0347(3) Uani 1 1 d . . . . .
I1 I 0.48602(5) 0.32149(6) 0.64438(2) 0.0342(3) Uani 1 1 d . . . . .
N1 N 0.6411(10) 0.6005(9) 0.6341(3) 0.047(3) Uani 1 1 d D . . . .
H1AB H 0.605878 0.531023 0.631094 0.057 Uiso 0.65(3) 1 calc R . . A 1
H1AA H 0.686129 0.613727 0.652543 0.057 Uiso 0.65(3) 1 calc R . . A 1
H1BD H 0.620714 0.533236 0.638233 0.057 Uiso 0.35(3) 1 calc R . . A 2
H1BC H 0.705301 0.641575 0.643168 0.057 Uiso 0.35(3) 1 calc R . . A 2
C2 C 0.5653(12) 0.6294(12) 0.6473(4) 0.054(4) Uani 1 1 d . . . . .
H2A H 0.583217 0.697369 0.637742 0.081 Uiso 1 1 calc GR . . . .
H2B H 0.566568 0.631629 0.673857 0.081 Uiso 1 1 calc GR . . . .
H2C H 0.496196 0.578333 0.638995 0.081 Uiso 1 1 calc GR . . . .
C1A C 0.7104(15) 0.6483(19) 0.5976(5) 0.058(5) Uani 0.65(3) 1 d D . . A 1
H1AC H 0.748645 0.724514 0.597860 0.069 Uiso 0.65(3) 1 calc R . . A 1
H1AD H 0.759035 0.622554 0.593917 0.069 Uiso 0.65(3) 1 calc R . . A 1
C1B C 0.632(4) 0.623(4) 0.5936(6) 0.058(5) Uani 0.35(3) 1 d D U . A 2
H1BA H 0.578807 0.556925 0.582978 0.069 Uiso 0.35(3) 1 calc R . . A 2
H1BB H 0.603643 0.669727 0.593290 0.069 Uiso 0.35(3) 1 calc R . . 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 I2 2.9770(7) 3_665 ?
Bi1 I2 2.9770(7) 2_655 ?
Bi1 I2 2.9770(7) . ?
Bi1 I1 3.1988(7) 2_655 ?
Bi1 I1 3.1987(7) . ?
Bi1 I1 3.1988(7) 3_665 ?
N1 C2 1.457(19) . ?
N1 C1A 1.60(3) . ?
N1 C1B 1.518(19) . ?
C1A C1A 1.517(19) 18_655 ?
C1B C1B 1.15(8) 18_655 ?

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 95.31(2) 3_665 2_655 ?
I2 Bi1 I2 95.31(2) 3_665 . ?
I2 Bi1 I2 95.31(2) 2_655 . ?
I2 Bi1 I1 89.45(2) 2_655 . ?
I2 Bi1 I1 89.45(2) . 3_665 ?
I2 Bi1 I1 86.82(2) 3_665 3_665 ?
I2 Bi1 I1 86.82(2) . . ?
I2 Bi1 I1 89.45(2) 3_665 2_655 ?
I2 Bi1 I1 174.57(3) 2_655 3_665 ?
I2 Bi1 I1 86.82(2) 2_655 2_655 ?
I2 Bi1 I1 174.57(3) . 2_655 ?
I2 Bi1 I1 174.57(3) 3_665 . ?
I1 Bi1 I1 88.21(2) 2_655 3_665 ?
I1 Bi1 I1 88.21(2) . 3_665 ?
I1 Bi1 I1 88.21(2) 2_655 . ?
C2 N1 C1A 123.7(13) . . ?
C2 N1 C1B 95.3(19) . . ?
C1A C1A N1 99(2) 18_655 . ?
C1B C1B N1 124(5) 18_655 . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.154
_oxdiff_exptl_absorpt_empirical_full_min 0.379
####################################################################### 
# 
# 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_b-1
_database_code_depnum_ccdc_archive 'CCDC 1905326'
loop_
_audit_author_name
_audit_author_address
'Jiangwei Zhang'
;Dalian Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;
_audit_creation_date             2019-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Bi2 I10), C4 H14 N2'
_chemical_formula_sum            'C4 H14 Bi I5 N2'
_chemical_formula_weight         933.65
_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   18.268(4)
_cell_length_b                   8.4939(17)
_cell_length_c                   10.927(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1695.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.291
_cell_measurement_theta_min      2.172
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    19.485
_exptl_absorpt_correction_T_max  0.142
_exptl_absorpt_correction_T_min  0.013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    3.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1600.0
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17071
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.291
_diffrn_reflns_theta_min         2.172
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_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                1785
_reflns_number_total             1819
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.495
_refine_diff_density_min         -3.825
_refine_diff_density_rms         0.576
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1334P)²+13.1620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1702
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C11 = N2-C5 = C5-C3 = N1-C3 = N1-C4
 1.5 with sigma of 0.02
 C11-C5
 2.5 with sigma of 0.02
 N2-C3
 2.5 with sigma of 0.02
 C3-C4
 2.5 with sigma of 0.02
 C5-N1
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C4, N1, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C4) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C5) = Uanis(N2) = Uanis(C11)
5. Others
 Fixed Sof: N1(0.5) H1A(0.5) H1B(0.5) N2(0.5) H2A(0.5) H2B(0.5) C3(0.5)
 H3A(0.5) H3B(0.5) C4(0.5) H4A(0.5) H4B(0.5) H4C(0.5) C5(0.5) H5A(0.5) H5B(0.5)
 C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
6.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
6.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C)
;
_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
Bi01 Bi 0.43442(3) 0.250000 0.69117(5) 0.0410(3) Uani 1 2 d S T P . .
I002 I 0.57785(8) 0.250000 0.82458(13) 0.0630(4) Uani 1 2 d S T P . .
I003 I 0.29034(6) 0.250000 0.53131(12) 0.0634(4) Uani 1 2 d S T P . .
I004 I 0.37493(6) 0.50281(11) 0.84620(10) 0.0679(4) Uani 1 1 d . . . . .
I005 I 0.500000 0.000000 0.500000 0.0784(5) Uani 1 2 d S T P . .
N1 N 0.322(2) 0.157(6) 0.172(6) 0.130(14) Uani 0.5 1 d D U . A -1
H1A H 0.323830 0.105716 0.100676 0.156 Uiso 0.5 1 calc R . . A -1
H1B H 0.298079 0.097618 0.224964 0.156 Uiso 0.5 1 calc R . . A -1
N2 N 0.198(2) 0.225(9) -0.018(3) 0.127(11) Uani 0.5 1 d D . . A -1
H2A H 0.241494 0.184265 -0.039448 0.152 Uiso 0.5 1 calc R . . A -1
H2B H 0.188296 0.303099 -0.069603 0.152 Uiso 0.5 1 calc R . . A -1
C3 C 0.282(2) 0.310(5) 0.154(5) 0.116(16) Uani 0.5 1 d D U . A -1
H3A H 0.307711 0.372515 0.093924 0.139 Uiso 0.5 1 calc R . . A -1
H3B H 0.282460 0.367404 0.230761 0.139 Uiso 0.5 1 calc R . . A -1
C4 C 0.400(2) 0.182(9) 0.217(8) 0.148(19) Uani 0.5 1 d D U . A -1
H4A H 0.430075 0.217606 0.151102 0.222 Uiso 0.5 1 calc GR . . A -1
H4B H 0.418632 0.085159 0.249173 0.222 Uiso 0.5 1 calc GR . . A -1
H4C H 0.399552 0.260383 0.281004 0.222 Uiso 0.5 1 calc GR . . A -1
C5 C 0.204(2) 0.291(6) 0.114(4) 0.127(11) Uani 0.5 1 d D U . A -1
H5A H 0.178631 0.221213 0.169349 0.152 Uiso 0.5 1 calc R . . A -1
H5B H 0.179710 0.393047 0.116775 0.152 Uiso 0.5 1 calc R . . A -1
C11 C 0.140(3) 0.100(8) -0.028(5) 0.127(11) Uani 0.5 1 d D . . A -1
H11A H 0.145242 0.027411 0.038170 0.190 Uiso 0.5 1 calc GR . . A -1
H11B H 0.145968 0.045502 -0.104607 0.190 Uiso 0.5 1 calc GR . . A -1
H11C H 0.092970 0.148844 -0.025361 0.190 Uiso 0.5 1 calc GR . . 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
Bi01 I002 2.9984(14) . ?
Bi01 I003 3.1589(13) . ?
Bi01 I004 2.9430(9) . ?
Bi01 I004 2.9430(9) 7_565 ?
Bi01 I005 3.2106(6) . ?
Bi01 I005 3.2106(6) 3_656 ?
N1 C3 1.505(19) . ?
N1 C4 1.52(2) . ?
N2 C5 1.548(19) . ?
N2 C11 1.50(2) . ?
C3 C5 1.50(2) . ?

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
I002 Bi01 I003 175.52(4) . . ?
I002 Bi01 I005 89.44(3) . 3_656 ?
I002 Bi01 I005 89.44(3) . . ?
I003 Bi01 I005 87.20(3) . 3_656 ?
I003 Bi01 I005 87.20(3) . . ?
I004 Bi01 I002 92.46(3) 7_565 . ?
I004 Bi01 I002 92.46(3) . . ?
I004 Bi01 I003 90.61(3) . . ?
I004 Bi01 I003 90.61(3) 7_565 . ?
I004 Bi01 I004 93.71(4) 7_565 . ?
I004 Bi01 I005 174.18(3) 7_565 3_656 ?
I004 Bi01 I005 91.70(2) 7_565 . ?
I004 Bi01 I005 91.70(2) . 3_656 ?
I004 Bi01 I005 174.18(3) . . ?
I005 Bi01 I005 82.814(19) . 3_656 ?
Bi01 I005 Bi01 180.0 . 5_656 ?
C3 N1 C4 112(2) . . ?
C5 N2 C11 111.8(19) . . ?
N1 C3 C5 115(2) . . ?
N2 C5 C3 111.9(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
