# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Weichuan_Zhang_PTB100K
_database_code_depnum_ccdc_archive 'CCDC 1847121'
_audit_update_record             
;
2018-06-04 deposited with the CCDC.
2018-10-09 downloaded from the CCDC.
;
_audit_creation_date             2016-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Bi0.5 I3, I1.5, 2(C3 H10 N)'
_chemical_formula_sum            'C6 H20 Bi0.50 I4.50 N2'
_chemical_formula_weight         795.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Bi I'
_chemical_oxdiff_usercomment     'C O H N Ni'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5733(4)
_cell_length_b                   12.1377(3)
_cell_length_c                   11.9395(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.720(3)
_cell_angle_gamma                90
_cell_volume                     1777.38(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8514
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      29.4240
_cell_measurement_theta_min      3.7280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.974
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20352
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.731
_diffrn_reflns_theta_min         3.322
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  29.00   1.00    3.97    --  -11.58 -99.00 -60.00   49
  2  ω    -20.00  29.00   1.00    3.97    --  -11.58 -99.00-150.00   49
  3  ω    -44.00  65.00   1.00    3.97    --  -11.58  77.00  60.00  109
  4  ω    -64.00  35.00   1.00    3.97    --   10.33 -38.00-180.00   99
  5  ω    -64.00  35.00   1.00    3.97    --   10.33 -38.00 -90.00   99
  6  ω    -84.00 -59.00   1.00    3.97    --  -11.58 -61.00 110.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0412839000
_diffrn_orient_matrix_UB_12      0.0256430000
_diffrn_orient_matrix_UB_13      -0.0420572000
_diffrn_orient_matrix_UB_21      0.0001919000
_diffrn_orient_matrix_UB_22      -0.0454237000
_diffrn_orient_matrix_UB_23      -0.0373038000
_diffrn_orient_matrix_UB_31      -0.0405187000
_diffrn_orient_matrix_UB_32      -0.0263234000
_diffrn_orient_matrix_UB_33      0.0234484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3721
_reflns_number_total             4492
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.066
_refine_diff_density_min         -1.047
_refine_diff_density_rms         0.219
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.046
_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)+(0.0129P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0397
_refine_ls_wR_factor_ref         0.0443
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, {H7A,H7B,H7C} of N7
 At 1.5 times of:
  All C(H,H,H) groups, {H14A,H14B,H14C} of N14
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C13(H13A,H13B), C12(H12A,H12B), C9(H9A,H9B)
2.b Idealised Me refined as rotating group:
 N7(H7A,H7B,H7C), N14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 1.0000 0.5000 0.5000 0.01122(6) Uani 1 2 d S T P . .
I2 I 0.72683(3) 0.46700(2) 0.98230(2) 0.02113(7) Uani 1 1 d . . . . .
I3 I 1.04797(2) 0.49248(2) 0.25861(2) 0.01349(7) Uani 1 1 d . . . . .
I4 I 1.00505(2) 0.75310(2) 0.49323(2) 0.01424(7) Uani 1 1 d . . . . .
I5 I 0.75633(2) 0.50360(2) 0.38928(2) 0.01441(7) Uani 1 1 d . . . . .
I6 I 0.5000 0.5000 1.0000 0.01728(9) Uani 1 2 d S T P . .
N7 N 0.8142(3) 0.2322(3) 0.7131(3) 0.0178(8) Uani 1 1 d . . . . .
H7A H 0.8188 0.2066 0.6445 0.021 Uiso 1 1 calc GR . . . .
H7B H 0.8436 0.1836 0.7669 0.021 Uiso 1 1 calc GR . . . .
H7C H 0.8500 0.2958 0.7263 0.021 Uiso 1 1 calc GR . . . .
N14 N 0.1693(3) 0.2033(3) 0.3067(3) 0.0190(8) Uani 1 1 d . . . . .
H14A H 0.1251 0.2529 0.2655 0.029 Uiso 1 1 calc GR . . . .
H14B H 0.1390 0.1772 0.3620 0.029 Uiso 1 1 calc GR . . . .
H14C H 0.1803 0.1483 0.2613 0.029 Uiso 1 1 calc GR . . . .
C8 C 0.6969(3) 0.2500(3) 0.7158(3) 0.0172(9) Uani 1 1 d . . . . .
H8A H 0.6918 0.2722 0.7925 0.021 Uiso 1 1 calc R . . . .
H8B H 0.6574 0.1813 0.6981 0.021 Uiso 1 1 calc R . . . .
C13 C 0.2757(4) 0.2562(3) 0.3591(3) 0.0192(9) Uani 1 1 d . . . . .
H13A H 0.3243 0.2019 0.4029 0.023 Uiso 1 1 calc R . . . .
H13B H 0.2642 0.3140 0.4114 0.023 Uiso 1 1 calc R . . . .
C12 C 0.3275(4) 0.3048(4) 0.2671(3) 0.0215(10) Uani 1 1 d . . . . .
H12A H 0.3354 0.2476 0.2128 0.026 Uiso 1 1 calc R . . . .
H12B H 0.2800 0.3613 0.2257 0.026 Uiso 1 1 calc R . . . .
C9 C 0.6449(3) 0.3369(3) 0.6312(4) 0.0213(10) Uani 1 1 d . . . . .
H9A H 0.6509 0.3158 0.5545 0.026 Uiso 1 1 calc R . . . .
H9B H 0.6827 0.4064 0.6499 0.026 Uiso 1 1 calc R . . . .
C11 C 0.4372(4) 0.3541(4) 0.3171(4) 0.0318(12) Uani 1 1 d . . . . .
H11A H 0.4669 0.3853 0.2567 0.048 Uiso 1 1 calc GR . . . .
H11B H 0.4853 0.2978 0.3556 0.048 Uiso 1 1 calc GR . . . .
H11C H 0.4297 0.4107 0.3710 0.048 Uiso 1 1 calc GR . . . .
C10 C 0.5256(4) 0.3506(4) 0.6345(4) 0.0269(11) Uani 1 1 d . . . . .
H10A H 0.4941 0.4083 0.5827 0.040 Uiso 1 1 calc GR . . . .
H10B H 0.5198 0.3693 0.7110 0.040 Uiso 1 1 calc GR . . . .
H10C H 0.4875 0.2829 0.6118 0.040 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.01175(12) 0.01065(10) 0.01158(11) -0.00035(8) 0.00328(9) -0.00002(8)
I2 0.02079(17) 0.02207(14) 0.02106(14) 0.00231(12) 0.00574(12) 0.00299(13)
I3 0.01530(15) 0.01396(13) 0.01238(13) -0.00060(10) 0.00554(11) 0.00094(10)
I4 0.01858(16) 0.01015(12) 0.01539(13) 0.00027(10) 0.00676(11) -0.00031(10)
I5 0.01080(15) 0.01605(13) 0.01650(14) 0.00020(10) 0.00324(11) -0.00017(10)
I6 0.0199(2) 0.01418(18) 0.01715(19) 0.00124(15) 0.00287(17) 0.00061(15)
N7 0.016(2) 0.0192(18) 0.0180(18) 0.0018(15) 0.0033(15) -0.0004(15)
N14 0.017(2) 0.0221(18) 0.0208(18) -0.0024(15) 0.0105(16) 0.0009(16)
C8 0.014(2) 0.019(2) 0.020(2) 0.0013(18) 0.0067(18) 0.0014(18)
C13 0.020(3) 0.015(2) 0.022(2) -0.0015(18) 0.0032(19) -0.0042(18)
C12 0.020(3) 0.025(2) 0.022(2) -0.0018(19) 0.010(2) -0.003(2)
C9 0.018(3) 0.018(2) 0.028(2) 0.0056(19) 0.005(2) -0.0008(19)
C11 0.028(3) 0.028(3) 0.043(3) -0.009(2) 0.014(2) -0.010(2)
C10 0.015(3) 0.027(2) 0.039(3) 0.006(2) 0.007(2) 0.003(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 I3 3.0731(3) 3_766 ?
Bi1 I3 3.0731(3) . ?
Bi1 I4 3.0742(3) . ?
Bi1 I4 3.0742(3) 3_766 ?
Bi1 I5 3.0582(3) . ?
Bi1 I5 3.0581(3) 3_766 ?
I2 I6 2.9333(3) . ?
I6 I2 2.9333(3) 3_667 ?
N7 C8 1.498(5) . ?
N14 C13 1.491(5) . ?
C8 C9 1.507(5) . ?
C13 C12 1.515(5) . ?
C12 C11 1.502(6) . ?
C9 C10 1.518(6) . ?

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_766 ?
I3 Bi1 I4 90.253(6) . 3_766 ?
I3 Bi1 I4 89.747(6) . . ?
I3 Bi1 I4 90.253(6) 3_766 . ?
I3 Bi1 I4 89.748(6) 3_766 3_766 ?
I4 Bi1 I4 180.0 3_766 . ?
I5 Bi1 I3 91.154(8) . 3_766 ?
I5 Bi1 I3 88.846(8) 3_766 3_766 ?
I5 Bi1 I3 91.155(7) 3_766 . ?
I5 Bi1 I3 88.845(8) . . ?
I5 Bi1 I4 90.064(7) 3_766 . ?
I5 Bi1 I4 89.936(7) . . ?
I5 Bi1 I4 89.936(7) 3_766 3_766 ?
I5 Bi1 I4 90.063(7) . 3_766 ?
I5 Bi1 I5 180.0 3_766 . ?
I2 I6 I2 180.0 3_667 . ?
N7 C8 C9 111.7(3) . . ?
N14 C13 C12 110.6(3) . . ?
C11 C12 C13 111.8(4) . . ?
C8 C9 C10 110.2(3) . . ?

_shelx_SHELXL_version_number     2014/7

_iucr_refine_instructions_details 
;

    57-1.res created by SHELXL-2014/7

TITL 57-1 in P21/c #14
REM reset to P21/c #14
CELL 0.71073 12.57332 12.13771 11.93948 90 102.7198 90
ZERR 4 0.00038 0.00028 0.00031 0 0.0028 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Bi I N
UNIT 24 80 2 18 8
 
L.S. 20
PLAN  20
BOND
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\57-1.hkl">
REM </olex2.extras>
 
WGHT    0.012900
FVAR       1.19196
BI1   3    1.000000    0.500000    0.500000    10.50000    0.01175    0.01065 =
         0.01158   -0.00035    0.00328   -0.00002
I2    4    0.726828    0.466999    0.982304    11.00000    0.02079    0.02207 =
         0.02106    0.00231    0.00574    0.00299
I3    4    1.047968    0.492477    0.258612    11.00000    0.01530    0.01396 =
         0.01238   -0.00060    0.00554    0.00094
I4    4    1.005054    0.753104    0.493232    11.00000    0.01858    0.01015 =
         0.01539    0.00027    0.00676   -0.00031
I5    4    0.756329    0.503603    0.389281    11.00000    0.01080    0.01605 =
         0.01650    0.00020    0.00324   -0.00017
I6    4    0.500000    0.500000    1.000000    10.50000    0.01995    0.01418 =
         0.01715    0.00124    0.00287    0.00061
N7    5    0.814231    0.232207    0.713125    11.00000    0.01606    0.01922 =
         0.01800    0.00182    0.00332   -0.00035
AFIX 137
H7A   2    0.818771    0.206614    0.644479    11.00000   -1.20000
H7B   2    0.843565    0.183641    0.766948    11.00000   -1.20000
H7C   2    0.850049    0.295794    0.726336    11.00000   -1.20000
AFIX   0
 
N14   5    0.169285    0.203332    0.306713    11.00000    0.01712    0.02206 =
         0.02083   -0.00236    0.01049    0.00093
AFIX 137
H14A  2    0.125119    0.252926    0.265546    11.00000   -1.50000
H14B  2    0.138954    0.177202    0.361971    11.00000   -1.50000
H14C  2    0.180305    0.148293    0.261334    11.00000   -1.50000
AFIX   0
 
C8    1    0.696894    0.250005    0.715840    11.00000    0.01407    0.01872 =
         0.02017    0.00135    0.00674    0.00137
AFIX  23
H8A   2    0.691827    0.272168    0.792547    11.00000   -1.20000
H8B   2    0.657424    0.181270    0.698088    11.00000   -1.20000
AFIX   0
 
C13   1    0.275651    0.256246    0.359141    11.00000    0.01982    0.01548 =
         0.02155   -0.00147    0.00323   -0.00420
AFIX  23
H13A  2    0.324301    0.201926    0.402879    11.00000   -1.20000
H13B  2    0.264151    0.313979    0.411394    11.00000   -1.20000
AFIX   0
C12   1    0.327471    0.304832    0.267098    11.00000    0.02048    0.02472 =
         0.02163   -0.00179    0.00995   -0.00251
AFIX  23
H12A  2    0.335412    0.247610    0.212815    11.00000   -1.20000
H12B  2    0.279978    0.361312    0.225698    11.00000   -1.20000
AFIX   0
 
C9    1    0.644911    0.336901    0.631216    11.00000    0.01776    0.01819 =
         0.02792    0.00557    0.00506   -0.00082
AFIX  23
H9A   2    0.650904    0.315778    0.554494    11.00000   -1.20000
H9B   2    0.682744    0.406393    0.649945    11.00000   -1.20000
AFIX   0
 
C11   1    0.437222    0.354088    0.317102    11.00000    0.02764    0.02778 =
         0.04305   -0.00915    0.01429   -0.01050
AFIX 137
H11A  2    0.466869    0.385327    0.256679    11.00000   -1.50000
H11B  2    0.485291    0.297761    0.355594    11.00000   -1.50000
H11C  2    0.429664    0.410663    0.370999    11.00000   -1.50000
AFIX   0
 
C10   1    0.525625    0.350618    0.634478    11.00000    0.01519    0.02663 =
         0.03924    0.00610    0.00656    0.00339
AFIX 137
H10A  2    0.494120    0.408298    0.582683    11.00000   -1.50000
H10B  2    0.519795    0.369347    0.711015    11.00000   -1.50000
H10C  2    0.487523    0.282885    0.611797    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  57-1 in P21/c #14
REM R1 =  0.0236 for    3721 Fo > 4sig(Fo)  and  0.0365 for all    4492 data
REM    125 parameters refined using      0 restraints
 
END  
     
WGHT      0.0129      0.0000 

REM Highest difference peak  1.066,  deepest hole -1.047,  1-sigma level  0.219
Q1    1   0.7245  0.5373  0.9780  11.00000  0.05    1.07
Q2    1   1.1407  0.5606  0.4634  11.00000  0.05    0.95
Q3    1   1.0581  0.5864  0.5326  11.00000  0.05    0.87
Q4    1   0.6792  0.3766  0.9282  11.00000  0.05    0.78
Q5    1   0.4188  0.3633  0.6205  11.00000  0.05    0.78
Q6    1   1.0643  0.5864  0.2396  11.00000  0.05    0.78
Q7    1   0.6754  0.1018  0.6782  11.00000  0.05    0.77
Q8    1   1.1007  0.5837  0.6068  11.00000  0.05    0.76
Q9    1   0.2567  0.3627  0.3798  11.00000  0.05    0.75
Q10   1   0.9391  0.6503  0.4202  11.00000  0.05    0.73
Q11   1   1.0593  0.3746  0.2597  11.00000  0.05    0.72
Q12   1   0.1571  0.3652  0.4689  11.00000  0.05    0.72
Q13   1  -0.0029  0.2648  0.3273  11.00000  0.05    0.72
Q14   1   0.8418  0.4704  1.0430  11.00000  0.05    0.71
Q15   1   1.0849  0.6130  0.4733  11.00000  0.05    0.71
Q16   1   0.6357  0.4349  0.3838  11.00000  0.05    0.71
Q17   1   1.0434  0.4146  0.3751  11.00000  0.05    0.71
Q18   1   0.1425  0.3356  0.2677  11.00000  0.05    0.70
Q19   1   1.0362  0.8523  0.6075  11.00000  0.05    0.70
Q20   1   1.1241  0.6416  0.5567  11.00000  0.05    0.69

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0236 for 3721 Fo > 4sig(Fo) and 0.0365 for all 20920 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 1.07, deepest hole -1.05
  REM Mean Shift 0, Max Shift -0.001.
  
  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0365
  REM R1_gt = 0.0236
  REM wR_ref = 0.0443
  REM GOOF = 1.046
  REM Shift_max = -0.001
  REM Shift_mean = 0
  REM Reflections_all = 20920
  REM Reflections_gt = 3721
  REM Parameters = n/a
  REM Hole = -1.05
  REM Peak = 1.07
  REM Flack = n/a
  
  
;
_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 2.444
_oxdiff_exptl_absorpt_empirical_full_min 0.643
####################################################################### 
# 
# 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_Weichuan_Zhang_PTB300K
_database_code_depnum_ccdc_archive 'CCDC 1869781'
_audit_update_record             
;
2018-09-25 deposited with the CCDC.
2018-10-09 downloaded from the CCDC.
;
_audit_creation_date             2018-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi I6, 2(I1.5), 4(C3 H10 N)'
_chemical_formula_sum            'C12 H40 Bi I9 N4'
_chemical_formula_weight         1591.56
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.0482(7)
_cell_length_b                   12.4277(8)
_cell_length_c                   12.7161(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.681(2)
_cell_angle_gamma                90
_cell_volume                     1864.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6207
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.186
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.835
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.683
_diffrn_ambient_temperature      299.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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                1901
_reflns_number_total             2235
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.096
_refine_diff_density_min         -1.384
_refine_diff_density_rms         0.351
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²+0.3253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1141
_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,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 C2-C3
 1.48 with sigma of 0.02
 C6-C5
 1.48 with sigma of 0.02
 C6-C4
 1.48 with sigma of 0.02
 C4-C3
 1.48 with sigma of 0.02
 N1-C2
 1.47 with sigma of 0.02
 N1-C5
 1.47 with sigma of 0.02
3. Others
 Fixed Sof: H1AA(0.5) H1AB(0.5) H1AC(0.5) H1BD(0.5) H1BE(0.5) H1BF(0.5)
 H4AA(0.5) H4AB(0.5) H4AC(0.5) H4BD(0.5) H4BE(0.5) H4BF(0.5) C3(0.5) H3A(0.5)
 H3B(0.5) C2(0.5) H2A(0.5) H2B(0.5) C5(0.5) H5A(0.5) H5B(0.5) C6(0.5) H6A(0.5)
 H6B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B)
4.b Idealised Me refined as rotating group:
 N1(H1AA,H1AB,H1AC), N1(H1BD,H1BE,H1BF), C4(H4AA,H4AB,H4AC), C4(H4BD,H4BE,H4BF)
;
_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 0.5000 0.5000 0.5000 0.05570(17) Uani 1 4 d S T P . .
I1 I 0.40010(7) 0.5000 0.25704(6) 0.0765(2) Uani 1 2 d S T P . .
I2 I 0.25593(5) 0.5000 0.53895(6) 0.0674(2) Uani 1 2 d S T P . .
I3 I 0.5000 0.25159(5) 0.5000 0.0685(2) Uani 1 2 d S T P . .
I4 I 1.01086(12) 0.5000 0.77090(11) 0.1313(4) Uani 1 2 d S T P . .
I5 I 1.0000 0.5000 1.0000 0.1017(4) Uani 1 4 d S T P . .
N1 N 0.7086(7) 0.7820(7) 0.3225(6) 0.096(2) Uani 1 1 d D . . . .
H1AA H 0.6864 0.8504 0.3164 0.115 Uiso 0.5 1 calc GR . . A 1
H1AB H 0.7712 0.7764 0.3732 0.115 Uiso 0.5 1 calc GR . . A 1
H1AC H 0.6541 0.7419 0.3404 0.115 Uiso 0.5 1 calc GR . . A 1
H1BD H 0.7603 0.8279 0.3084 0.115 Uiso 0.5 1 calc GR . . B 2
H1BE H 0.7426 0.7306 0.3662 0.115 Uiso 0.5 1 calc GR . . B 2
H1BF H 0.6596 0.8169 0.3539 0.115 Uiso 0.5 1 calc GR . . B 2
C4 C 0.659(2) 0.6457(15) 0.0522(13) 0.197(9) Uani 1 1 d D . . . .
H4AA H 0.6466 0.7071 0.0055 0.296 Uiso 0.5 1 calc GR . . C 1
H4AB H 0.6067 0.5896 0.0230 0.296 Uiso 0.5 1 calc GR . . C 1
H4AC H 0.7350 0.6204 0.0583 0.296 Uiso 0.5 1 calc GR . . C 1
H4BD H 0.6918 0.6743 -0.0045 0.296 Uiso 0.5 1 calc GR . . D 2
H4BE H 0.5814 0.6691 0.0427 0.296 Uiso 0.5 1 calc GR . . D 2
H4BF H 0.6611 0.5685 0.0504 0.296 Uiso 0.5 1 calc GR . . D 2
C3 C 0.640(2) 0.676(3) 0.1572(19) 0.147(12) Uani 0.5 1 d D . . E 1
H3A H 0.6341 0.6110 0.1983 0.177 Uiso 0.5 1 calc R . . E 1
H3B H 0.5691 0.7144 0.1490 0.177 Uiso 0.5 1 calc R . . E 1
C2 C 0.732(2) 0.744(2) 0.2169(18) 0.135(10) Uani 0.5 1 d D . . E 1
H2A H 0.7427 0.8053 0.1733 0.163 Uiso 0.5 1 calc R . . E 1
H2B H 0.8025 0.7027 0.2302 0.163 Uiso 0.5 1 calc R . . E 1
C5 C 0.6478(19) 0.7331(19) 0.2216(16) 0.111(7) Uiso 0.5 1 d D . . E 2
H5A H 0.5969 0.6781 0.2382 0.134 Uiso 0.5 1 calc R . . E 2
H5B H 0.6022 0.7879 0.1787 0.134 Uiso 0.5 1 calc R . . E 2
C6 C 0.724(2) 0.685(3) 0.159(2) 0.156(12) Uiso 0.5 1 d D . . E 2
H6A H 0.7646 0.6253 0.1984 0.188 Uiso 0.5 1 calc R . . E 2
H6B H 0.7796 0.7380 0.1472 0.188 Uiso 0.5 1 calc R . . E 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.0530(3) 0.0558(3) 0.0599(3) 0.000 0.0151(2) 0.000
I1 0.0837(5) 0.0906(5) 0.0557(4) 0.000 0.0153(3) 0.000
I2 0.0539(3) 0.0748(4) 0.0772(5) 0.000 0.0224(3) 0.000
I3 0.0701(4) 0.0504(3) 0.0891(5) 0.000 0.0260(3) 0.000
I4 0.1158(8) 0.1696(11) 0.1041(8) 0.000 0.0119(7) 0.000
I5 0.0851(7) 0.0995(8) 0.1121(11) 0.000 -0.0003(7) 0.000
N1 0.096(5) 0.129(6) 0.063(4) -0.003(4) 0.017(4) -0.024(5)
C4 0.27(2) 0.202(17) 0.124(14) -0.068(13) 0.052(15) -0.037(18)
C3 0.14(2) 0.20(3) 0.106(19) -0.08(2) 0.032(17) -0.04(2)
C2 0.13(2) 0.099(16) 0.20(3) -0.021(18) 0.09(2) -0.029(14)

_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 3.0803(8) . ?
Bi1 I1 3.0803(8) 5_666 ?
Bi1 I2 3.0793(6) . ?
Bi1 I2 3.0793(6) 5_666 ?
Bi1 I3 3.0872(6) . ?
Bi1 I3 3.0873(6) 5_666 ?
I4 I5 2.9425(14) . ?
I5 I4 2.9425(14) 5_767 ?
N1 C2 1.507(16) . ?
N1 C5 1.474(16) . ?
C4 C3 1.446(16) . ?
C4 C6 1.506(18) . ?
C3 C2 1.477(18) . ?
C5 C6 1.463(18) . ?

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 I1 180.0 5_666 . ?
I1 Bi1 I3 90.0 5_666 . ?
I1 Bi1 I3 90.0 5_666 5_666 ?
I1 Bi1 I3 90.0 . 5_666 ?
I1 Bi1 I3 90.0 . . ?
I2 Bi1 I1 88.25(2) 5_666 5_666 ?
I2 Bi1 I1 91.75(2) . 5_666 ?
I2 Bi1 I1 91.75(2) 5_666 . ?
I2 Bi1 I1 88.25(2) . . ?
I2 Bi1 I2 180.0 5_666 . ?
I2 Bi1 I3 90.0 5_666 5_666 ?
I2 Bi1 I3 90.0 5_666 . ?
I2 Bi1 I3 90.0 . . ?
I2 Bi1 I3 90.0 . 5_666 ?
I3 Bi1 I3 180.0 . 5_666 ?
I4 I5 I4 180.0 5_767 . ?
C4 C3 C2 112.5(17) . . ?
C3 C2 N1 112.4(14) . . ?
C6 C5 N1 112.7(17) . . ?
C5 C6 C4 110.5(18) . . ?

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
N1 C5 C6 C4 -175(2) . . . . ?
C4 C3 C2 N1 175(2) . . . . ?

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

data_Weichuan_Zhang_PTB210K
_database_code_depnum_ccdc_archive 'CCDC 1847122'
_audit_update_record             
;
2018-06-04 deposited with the CCDC.
2018-10-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi I6, 2(I1.5), 4(C3 H10 N)'
_chemical_formula_sum            'C12 H40 Bi I9 N4'
_chemical_formula_weight         1591.56
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.0240(7)
_cell_length_b                   12.3072(8)
_cell_length_c                   12.6205(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.258(2)
_cell_angle_gamma                90
_cell_volume                     1825.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9478
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.369
_shelx_estimated_absorpt_T_min   0.190
_exptl_absorpt_coefficient_mu    12.450
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1358 before and 0.0876 after correction. The Ratio of minimum to maximum transmission is 0.4015. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.896
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16367
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.396
_diffrn_ambient_temperature      210.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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                2085
_reflns_number_total             2185
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.464
_refine_diff_density_min         -4.279
_refine_diff_density_rms         0.517
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.276
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         2185
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.277
_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)+(0.0656P)²+3.3438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1207
_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,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C2
 1.48 with sigma of 0.01
 C6-C4
 1.5 with sigma of 0.01
 C3-C4
 1.5 with sigma of 0.01
3. Others
 Sof(H1BD)=Sof(H1BE)=Sof(H1BF)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=
 Sof(H6B)=FVAR(1)
4.a Riding coordinates:
 C4(H4C,H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
4.b Idealised Me refined as rotating group:
 N1(H1BD,H1BE,H1BF), N1(H1AA,H1AB,H1AC)
;
_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 1.0000 0.5000 0.5000 0.03404(16) Uani 1 4 d S T P . .
I1 I 0.75746(5) 0.5000 0.54290(5) 0.04076(19) Uani 1 2 d S T P . .
I2 I 1.0000 0.75064(5) 0.5000 0.04194(19) Uani 1 2 d S T P . .
I3 I 0.89512(6) 0.5000 0.25561(5) 0.0488(2) Uani 1 2 d S T P . .
I4 I 0.5000 0.5000 0.0000 0.0740(4) Uani 1 4 d S T P . .
I5 I 0.48734(12) 0.5000 0.22989(9) 0.1002(4) Uani 1 2 d S T P . .
N1 N 0.7067(7) 0.2822(7) 0.3228(6) 0.0611(19) Uani 1 1 d D . . . .
H1BD H 0.6332 0.3017 0.3145 0.073 Uiso 0.46(3) 1 calc GR . . A 2
H1BE H 0.7515 0.3392 0.3480 0.073 Uiso 0.46(3) 1 calc GR . . A 2
H1BF H 0.7218 0.2269 0.3703 0.073 Uiso 0.46(3) 1 calc GR . . A 2
H1AA H 0.7648 0.3236 0.3116 0.073 Uiso 0.54(3) 1 calc GR . . A 1
H1AB H 0.7338 0.2286 0.3697 0.073 Uiso 0.54(3) 1 calc GR . . A 1
H1AC H 0.6579 0.3235 0.3504 0.073 Uiso 0.54(3) 1 calc GR . . A 1
C4 C 0.6583(19) 0.1477(13) 0.0464(11) 0.131(7) Uani 1 1 d D . . . .
H4C H 0.6415 0.2124 0.0020 0.196 Uiso 1 1 d R . . A .
H4A H 0.6046 0.0908 0.0174 0.196 Uiso 1 1 d R . . . .
H4B H 0.7350 0.1234 0.0461 0.196 Uiso 1 1 d R . . . .
C2 C 0.7293(17) 0.2473(19) 0.2160(13) 0.066(7) Uani 0.46(3) 1 d D . . A 2
H2A H 0.7337 0.3120 0.1717 0.079 Uiso 0.46(3) 1 d R . . A 2
H2B H 0.8031 0.2104 0.2275 0.079 Uiso 0.46(3) 1 d R . . A 2
C3 C 0.641(3) 0.173(2) 0.1573(14) 0.072(8) Uani 0.46(3) 1 d D . . A 2
H3A H 0.6430 0.1057 0.1984 0.086 Uiso 0.46(3) 1 d R . . A 2
H3B H 0.5661 0.2064 0.1520 0.086 Uiso 0.46(3) 1 d R . . A 2
C5 C 0.647(2) 0.2350(17) 0.2198(17) 0.076(8) Uani 0.54(3) 1 d . . . A 1
H5A H 0.6004 0.2914 0.1771 0.091 Uiso 0.54(3) 1 d R . . A 1
H5B H 0.5965 0.1776 0.2350 0.091 Uiso 0.54(3) 1 d R . . A 1
C6 C 0.722(3) 0.186(2) 0.1561(16) 0.104(10) Uani 0.54(3) 1 d D . . A 1
H6A H 0.7654 0.1260 0.1957 0.125 Uiso 0.54(3) 1 d R . . A 1
H6B H 0.7761 0.2419 0.1436 0.125 Uiso 0.54(3) 1 d R . . A 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.0338(3) 0.0348(3) 0.0356(3) 0.000 0.01212(18) 0.000
I1 0.0347(3) 0.0446(3) 0.0464(4) 0.000 0.0165(3) 0.000
I2 0.0438(3) 0.0316(3) 0.0543(4) 0.000 0.0193(3) 0.000
I3 0.0572(4) 0.0565(4) 0.0345(3) 0.000 0.0138(3) 0.000
I4 0.0599(7) 0.0908(9) 0.0655(7) 0.000 0.0007(6) 0.000
I5 0.0830(7) 0.1525(12) 0.0618(6) 0.000 0.0078(5) 0.000
N1 0.061(4) 0.076(5) 0.047(4) 0.000(3) 0.011(3) -0.019(4)
C4 0.20(2) 0.110(11) 0.089(10) -0.043(9) 0.049(12) -0.033(13)
C2 0.041(11) 0.079(15) 0.083(15) -0.009(12) 0.026(10) -0.018(9)
C3 0.086(17) 0.090(17) 0.048(11) -0.019(11) 0.031(11) -0.028(14)
C5 0.088(17) 0.068(11) 0.066(12) -0.005(10) 0.002(10) -0.021(10)
C6 0.14(3) 0.098(19) 0.091(18) -0.005(15) 0.061(19) 0.007(19)

_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 3.0770(6) . ?
Bi1 I1 3.0770(6) 5_766 ?
Bi1 I2 3.0847(6) 5_766 ?
Bi1 I2 3.0847(6) . ?
Bi1 I3 3.0744(7) 5_766 ?
Bi1 I3 3.0744(7) . ?
I4 I5 2.9374(12) 5_665 ?
I4 I5 2.9375(12) . ?
N1 H1BD 0.9000 . ?
N1 H1BE 0.9000 . ?
N1 H1BF 0.9000 . ?
N1 H1AA 0.9000 . ?
N1 H1AB 0.9000 . ?
N1 H1AC 0.9000 . ?
N1 C2 1.494(9) . ?
N1 C5 1.46(2) . ?
C4 H4C 0.9701 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.491(9) . ?
C4 C6 1.510(10) . ?
C2 H2A 0.9799 . ?
C2 H2B 0.9799 . ?
C2 C3 1.47(3) . ?
C3 H3A 0.9801 . ?
C3 H3B 0.9800 . ?
C5 H5A 0.9801 . ?
C5 H5B 0.9801 . ?
C5 C6 1.46(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9801 . ?

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 I1 180.0 . 5_766 ?
I1 Bi1 I2 90.0 5_766 . ?
I1 Bi1 I2 90.0 5_766 5_766 ?
I1 Bi1 I2 90.0 . 5_766 ?
I1 Bi1 I2 90.0 . . ?
I2 Bi1 I2 180.0 . 5_766 ?
I3 Bi1 I1 91.471(19) . 5_766 ?
I3 Bi1 I1 88.529(19) 5_766 5_766 ?
I3 Bi1 I1 88.530(19) . . ?
I3 Bi1 I1 91.471(19) 5_766 . ?
I3 Bi1 I2 90.0 5_766 5_766 ?
I3 Bi1 I2 90.0 . 5_766 ?
I3 Bi1 I2 90.0 5_766 . ?
I3 Bi1 I2 90.0 . . ?
I3 Bi1 I3 180.0 . 5_766 ?
I5 I4 I5 180.0 5_665 . ?
H1BD N1 H1BE 109.5 . . ?
H1BD N1 H1BF 109.5 . . ?
H1BE N1 H1BF 109.5 . . ?
H1AA N1 H1AB 109.5 . . ?
H1AA N1 H1AC 109.5 . . ?
H1AB N1 H1AC 109.5 . . ?
C2 N1 H1BD 109.5 . . ?
C2 N1 H1BE 109.5 . . ?
C2 N1 H1BF 109.5 . . ?
C5 N1 H1AA 109.5 . . ?
C5 N1 H1AB 109.5 . . ?
C5 N1 H1AC 109.5 . . ?
H4C C4 H4A 109.5 . . ?
H4C C4 H4B 109.4 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 108.3 . . ?
C3 C4 H4A 107.1 . . ?
C3 C4 H4B 112.9 . . ?
C6 C4 H4C 106.0 . . ?
C6 C4 H4A 137.8 . . ?
C6 C4 H4B 78.6 . . ?
N1 C2 H2A 108.8 . . ?
N1 C2 H2B 109.4 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 N1 112.5(14) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 108.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 C4 112.1(17) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 107.6 . . ?
N1 C5 H5A 108.8 . . ?
N1 C5 H5B 108.6 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 N1 114.4(19) . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 107.1 . . ?
C4 C6 H6A 110.0 . . ?
C4 C6 H6B 107.3 . . ?
C5 C6 C4 113(2) . . ?
C5 C6 H6A 110.7 . . ?
C5 C6 H6B 107.9 . . ?
H6A C6 H6B 108.2 . . ?

_shelx_res_file                  
;
    57.res created by SHELXL-2014/7

TITL
REM 87 parameters refined using 3 restraints
REM Highest difference peak 1.456, deepest hole -4.277, 1-sigma level 0.517
CELL 0.71073 12.024 12.3072 12.6205 90 102.258 90
ZERR 2 0.0007 0.0008 0.0008 0 0.002 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H Bi I N
UNIT 24 80 2 18 8
DFIX 1.48 0.01 N1 C2
DFIX 1.5 0.01 C6 C4
DFIX 1.5 0.01 C3 C4

L.S. 20
PLAN  -35 0 0
SIZE 0.2 0.15 0.1
TEMP -63
GRID
BOND $H
fmap 2
acta
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\57.hkl">
REM </olex2.extras>

WGHT    0.065600    3.343800
FVAR       0.20726   0.54025
BI1   3    1.000000    0.500000    0.500000    10.25000    0.03379    0.03485 =
         0.03560    0.00000    0.01212    0.00000
I1    4    0.757465    0.500000    0.542900    10.50000    0.03471    0.04460 =
         0.04645    0.00000    0.01647    0.00000
I2    4    1.000000    0.750641    0.500000    10.50000    0.04381    0.03160 =
         0.05434    0.00000    0.01927    0.00000
I3    4    0.895125    0.500000    0.255609    10.50000    0.05724    0.05651 =
         0.03446    0.00000    0.01380    0.00000
I4    4    0.500000    0.500000    0.000000    10.25000    0.05991    0.09084 =
         0.06554    0.00000    0.00069    0.00000
I5    4    0.487336    0.500000    0.229892    10.50000    0.08301    0.15250 =
         0.06180    0.00000    0.00778    0.00000
N1    5    0.706706    0.282231    0.322806    11.00000    0.06067    0.07556 =
         0.04701    0.00034    0.01112   -0.01855
PART 2
AFIX 137
H1BD  2    0.633204    0.301691    0.314462   -21.00000   -1.20000
H1BE  2    0.751510    0.339180    0.348035   -21.00000   -1.20000
H1BF  2    0.721779    0.226862    0.370275   -21.00000   -1.20000
AFIX 137
PART 0
PART 1
H1AA  2    0.764836    0.323617    0.311595    21.00000   -1.20000
H1AB  2    0.733817    0.228626    0.369712    21.00000   -1.20000
H1AC  2    0.657942    0.323478    0.350445    21.00000   -1.20000
AFIX   0
PART 0
C4    1    0.658331    0.147674    0.046402    11.00000    0.20109    0.11006 =
         0.08870   -0.04338    0.04896   -0.03324
AFIX   3
H4C   2    0.641461    0.212364    0.001972    11.00000   -1.50000
H4A   2    0.604581    0.090814    0.017412    11.00000   -1.50000
H4B   2    0.734991    0.123364    0.046062    11.00000   -1.50000
AFIX   0
PART 2
C2    1    0.729329    0.247297    0.215952   -21.00000    0.04129    0.07921 =
         0.08295   -0.00896    0.02624   -0.01797
AFIX   3
H2A   2    0.733729    0.311967    0.171732   -21.00000   -1.20000
H2B   2    0.803129    0.210387    0.227492   -21.00000   -1.20000
AFIX   0
C3    1    0.641316    0.173476    0.157275   -21.00000    0.08579    0.08963 =
         0.04780   -0.01911    0.03061   -0.02785
AFIX   3
H3A   2    0.643026    0.105726    0.198405   -21.00000   -1.20000
H3B   2    0.566126    0.206386    0.152015   -21.00000   -1.20000
AFIX   0
PART 0
PART 1
C5    1    0.647403    0.235040    0.219845    21.00000    0.08765    0.06789 =
         0.06639   -0.00457    0.00221   -0.02143
AFIX   3
H5A   2    0.600443    0.291360    0.177125    21.00000   -1.20000
H5B   2    0.596533    0.177590    0.235025    21.00000   -1.20000
AFIX   0
C6    1    0.722106    0.186229    0.156106    21.00000    0.13903    0.09846 =
         0.09053   -0.00532    0.06081    0.00696
AFIX   3
H6A   2    0.765436    0.125999    0.195726    21.00000   -1.20000
H6B   2    0.776146    0.241929    0.143596    21.00000   -1.20000
AFIX   0
HKLF 4

REM
REM R1 =  0.0406 for    2085 Fo > 4sig(Fo)  and  0.0436 for all    2185 data
REM     88 parameters refined using      3 restraints

END

WGHT      0.0656      3.3316

REM Highest difference peak  1.464,  deepest hole -4.279,  1-sigma level  0.517
Q1    1   0.7650  0.5000  0.6693  10.50000  0.05    1.46
Q2    1   0.6019  0.4832  0.5683  11.00000  0.05    1.45
Q3    1   0.6951  0.5000  0.6263  10.50000  0.05    1.39
Q4    1   0.7814  0.5000  0.8428  10.50000  0.05    1.37
Q5    1   0.7807  0.4407  0.7698  11.00000  0.05    1.24
Q6    1   0.7277  0.5000  0.8181  10.50000  0.05    1.23
Q7    1   0.7630  0.4158  0.7118  11.00000  0.05    1.06
Q8    1   0.5000  0.4249  0.5000  10.50000  0.05    1.05
Q9    1   0.9019  0.5000  0.9577  10.50000  0.05    1.00
Q10   1   0.9153  0.5000  1.0966  10.50000  0.05    0.94
Q11   1   0.8776  0.4711  0.9190  11.00000  0.05    0.94
Q12   1   0.6798  0.2948  0.4967  11.00000  0.05    0.94
Q13   1   0.6627  0.2474  0.4968  11.00000  0.05    0.92
Q14   1   0.7386  0.3602  0.5106  11.00000  0.05    0.90
Q15   1   0.6798  0.4311  0.7530  11.00000  0.05    0.89
Q16   1   0.6980  0.5849  0.4845  11.00000  0.05    0.86
Q17   1   0.5866  0.5000  0.7876  10.50000  0.05    0.86
Q18   1   0.6768  0.2524  0.0435  11.00000  0.05    0.80
Q19   1   0.9185  0.5000  1.0212  10.50000  0.05    0.78
Q20   1   0.9046  0.5324  1.0056  11.00000  0.05    0.78
Q21   1   0.9585  0.4259  0.9758  11.00000  0.05    0.72
Q22   1   0.5227  0.4689  0.6556  11.00000  0.05    0.70
Q23   1   0.6656  0.2459  0.1259  11.00000  0.05    0.69
Q24   1   0.6390  0.2496 -0.0193  11.00000  0.05    0.68
Q25   1   0.6839  0.2732  0.8021  11.00000  0.05    0.65
Q26   1   0.9986  0.5394  1.1213  11.00000  0.05    0.64
Q27   1   0.7000  0.3171  0.7551  11.00000  0.05    0.64
Q28   1   0.5764  0.4313  0.7051  11.00000  0.05    0.63
Q29   1   0.5580  0.4411  0.6845  11.00000  0.05    0.63
Q30   1   0.6978  0.2394  0.7457  11.00000  0.05    0.63
Q31   1   0.5230  0.4456  0.7979  11.00000  0.05    0.61
Q32   1   0.0046  0.2293  0.3323  11.00000  0.05    0.57
Q33   1   0.5372  0.4194  0.6047  11.00000  0.05    0.57
Q34   1   0.6700  0.3046 -0.0157  11.00000  0.05    0.51
Q35   1   0.7069  0.1899  0.0016  11.00000  0.05    0.50
;
_shelx_res_checksum              16190
_olex2_submission_special_instructions 'No special instructions were received'
