# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_Compound_2L_100K
_database_code_depnum_ccdc_archive 'CCDC 1915340'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2020-04-01 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2018-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'

# start Validation Reply Form
_vrf_PLAT029_Compound_2L_100K    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.734 Why?  
RESPONSE: This low value is due to the kappa-goniometer being unavailable
at the time of the data collection.
;
_vrf_PLAT911_Compound_2L_100K    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.595       1248 Report
RESPONSE: Missing cusp of data due to rotation about one axis only (the 
kappa-goniometer was unavailable at the time of the data collection).
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, 3(C H6 N)'
_chemical_formula_sum            'C3 H18 Bi2 I9 N3'
_chemical_formula_weight         1656.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C3 H18 Bi2 I9 N3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 0.0015 '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 -3.0839 9.9321 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4830 1.6974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0058 0.0029 '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                   8.4972(3)
_cell_length_b                   14.6869(5)
_cell_length_c                   21.5538(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.647(4)
_cell_angle_gamma                90
_cell_volume                     2688.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3403
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7560
_cell_measurement_theta_min      2.4330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.942
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    4.092
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.734
_diffrn_reflns_Laue_measured_fraction_max 0.734
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3917
_diffrn_reflns_point_group_measured_fraction_full 0.734
_diffrn_reflns_point_group_measured_fraction_max 0.734
_diffrn_reflns_theta_full        23.891
_diffrn_reflns_theta_max         23.891
_diffrn_reflns_theta_min         1.810
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.734
_diffrn_measured_fraction_theta_max 0.734
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00 360.00   0.25    2.00    --    0.00   0.00   0.00 1440
;
_oxdiff_twin_items               4
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.2928 8265 6406 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.2247 0 2655 nmt 0.5007 0.5009 0.0002 -1.4970 0.4997 -0.0021 0.0371 -0.0377
0.9996
3 0.2179 0 2095 nmt -0.4990 0.5016 0.0001 -1.4977 -0.5000 0.0003 0.1166 -0.0371
1.0001
4 0.2645 0 5365 nmt 0.9994 0.0010 0.0010 0.0010 -1.0009 0.0007 -0.1470 0.0004
-0.9998
_oxdiff_twin_integration_method  simultaneous
_twin_special_details            
;
Component 2 rotated by 60.0237° 
 around [-0.00 0.00 -1.00] (reciprocal) or [-0.07 0.00 -1.00] (direct)
Component 3 rotated by -119.9933° 
 around [0.00 -0.00 1.00] (reciprocal) or [0.08 0.00 1.00] (direct)
Component 4 rotated by 179.9846° 
 around [1.00 0.00 -0.07] (reciprocal) or [1.00 0.00 -0.00] (direct)
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0476675000
_diffrn_orient_matrix_UB_12      0.0370785000
_diffrn_orient_matrix_UB_13      -0.0025302000
_diffrn_orient_matrix_UB_21      -0.0034084000
_diffrn_orient_matrix_UB_22      0.0022380000
_diffrn_orient_matrix_UB_23      0.0314656000
_diffrn_orient_matrix_UB_31      0.0642902000
_diffrn_orient_matrix_UB_32      0.0276835000
_diffrn_orient_matrix_UB_33      0.0009234000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6804
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3144
_reflns_number_total             3917
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         3.658
_refine_diff_density_min         -3.373
_refine_diff_density_rms         0.901
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0920
_refine_ls_restrained_S_all      1.206
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2803
_refine_ls_wR_factor_ref         0.2867
_refine_special_details          
;
 Refined as a 4-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.285(10)
 0.213(6) 0.188(6) 0.314(5)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
4. Rigid body (RIGU) restrains
 C1, C2, C3, N1, N2, N3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), N2(H2A,H2B,H2C), C2(H2D,H2E,H2F), N3(H3A,
 H3B,H3C), C3(H3D,H3E,H3F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.51889(16) 0.16585(9) 0.15826(6) 0.0240(4) Uani 1 1 d . . . . .
Bi2 Bi 0.48333(16) 0.17046(9) 0.34674(6) 0.0240(5) Uani 1 1 d . . . . .
I1 I 0.8006(3) 0.0945(2) 0.09655(11) 0.0347(7) Uani 1 1 d . . . . .
I2 I 0.3013(3) 0.07176(18) 0.06678(11) 0.0325(7) Uani 1 1 d . . . . .
I3 I 0.5056(3) 0.34036(19) 0.08606(12) 0.0319(7) Uani 1 1 d . . . . .
I4 I 0.5212(3) -0.0006(2) 0.25354(8) 0.0304(7) Uani 1 1 d . . . . .
I5 I 0.7408(3) 0.26067(18) 0.25825(11) 0.0327(7) Uani 1 1 d . . . . .
I6 I 0.2276(3) 0.23824(18) 0.23744(11) 0.0319(7) Uani 1 1 d . . . . .
I7 I 0.7322(3) 0.0933(2) 0.42769(11) 0.0343(7) Uani 1 1 d . . . . .
I8 I 0.2230(3) 0.0896(2) 0.41627(11) 0.0344(7) Uani 1 1 d . . . . .
I9 I 0.4799(4) 0.34232(19) 0.41897(12) 0.0315(7) Uani 1 1 d . . . . .
N1 N 0.070(4) 0.3278(19) 0.4565(12) 0.044(7) Uani 1 1 d . U . . .
H1A H 0.027780 0.363115 0.486415 0.053 Uiso 1 1 calc GR . . . .
H1B H 0.170053 0.346619 0.449508 0.053 Uiso 1 1 calc GR . . . .
H1C H 0.071747 0.268693 0.469206 0.053 Uiso 1 1 calc GR . . . .
C1 C -0.028(4) 0.336(2) 0.3976(15) 0.037(8) Uani 1 1 d . U . . .
H1D H -0.080169 0.277651 0.388726 0.055 Uiso 1 1 calc GR . . . .
H1E H 0.040100 0.351700 0.363245 0.055 Uiso 1 1 calc GR . . . .
H1F H -0.107295 0.383499 0.402436 0.055 Uiso 1 1 calc GR . . . .
N2 N 0.084(3) 0.2823(19) 0.0678(14) 0.050(8) Uani 1 1 d . U . . .
H2A H 0.142176 0.266188 0.102101 0.060 Uiso 1 1 calc GR . . . .
H2B H 0.148886 0.297717 0.036718 0.060 Uiso 1 1 calc GR . . . .
H2C H 0.022185 0.234525 0.055442 0.060 Uiso 1 1 calc GR . . . .
C2 C -0.019(5) 0.362(3) 0.083(2) 0.055(11) Uani 1 1 d . U . . .
H2D H -0.042505 0.361084 0.127110 0.083 Uiso 1 1 calc GR . . . .
H2E H -0.117236 0.358839 0.058122 0.083 Uiso 1 1 calc GR . . . .
H2F H 0.036299 0.418865 0.073247 0.083 Uiso 1 1 calc GR . . . .
N3 N 0.947(4) 0.043(3) 0.2791(17) 0.075(11) Uani 1 1 d . U . . .
H3A H 0.921528 0.015513 0.315332 0.090 Uiso 1 1 calc GR . . . .
H3B H 0.858383 0.053460 0.255748 0.090 Uiso 1 1 calc GR . . . .
H3C H 0.996996 0.096494 0.287482 0.090 Uiso 1 1 calc GR . . . .
C3 C 1.054(6) -0.018(3) 0.2443(17) 0.057(10) Uani 1 1 d . U . . .
H3D H 1.089561 -0.068374 0.271163 0.086 Uiso 1 1 calc GR . . . .
H3E H 1.146018 0.016717 0.231110 0.086 Uiso 1 1 calc GR . . . .
H3F H 0.997932 -0.042602 0.207670 0.086 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 0.0198(9) 0.0186(9) 0.0336(8) 0.0005(5) 0.0022(5) 0.0015(6)
Bi2 0.0193(9) 0.0194(9) 0.0336(8) 0.0003(5) 0.0019(5) -0.0016(7)
I1 0.0280(15) 0.0329(15) 0.0436(13) 0.0018(10) 0.0102(10) 0.0070(11)
I2 0.0281(14) 0.0284(14) 0.0408(12) -0.0010(9) -0.0023(9) -0.0067(10)
I3 0.0307(16) 0.0250(16) 0.0399(14) 0.0043(9) 0.0016(10) -0.0010(11)
I4 0.0358(15) 0.0188(16) 0.0369(14) 0.0007(7) 0.0038(10) 0.0013(9)
I5 0.0273(15) 0.0344(14) 0.0365(12) -0.0022(9) 0.0030(9) -0.0127(11)
I6 0.0246(15) 0.0330(14) 0.0384(12) 0.0023(9) 0.0043(9) 0.0086(10)
I7 0.0291(15) 0.0337(15) 0.0399(12) 0.0006(9) -0.0021(10) 0.0084(11)
I8 0.0286(15) 0.0331(15) 0.0420(13) 0.0026(10) 0.0088(10) -0.0051(11)
I9 0.0307(15) 0.0244(16) 0.0395(14) -0.0030(9) 0.0040(10) 0.0028(11)
N1 0.054(19) 0.041(19) 0.037(13) 0.004(12) 0.002(12) -0.006(14)
C1 0.025(14) 0.051(17) 0.035(12) -0.003(12) 0.013(10) -0.003(13)
N2 0.046(15) 0.047(14) 0.058(15) 0.001(12) 0.013(12) 0.011(12)
C2 0.051(18) 0.041(15) 0.075(19) -0.023(14) 0.006(14) 0.003(13)
N3 0.065(18) 0.078(17) 0.082(18) 0.009(14) 0.009(14) 0.021(14)
C3 0.056(17) 0.058(17) 0.058(17) 0.016(13) 0.005(13) 0.009(15)

_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 2.963(3) . ?
Bi1 I2 3.001(3) . ?
Bi1 I3 2.999(3) . ?
Bi1 I4 3.193(3) . ?
Bi1 I5 3.148(3) . ?
Bi1 I6 3.227(3) . ?
Bi2 I4 3.239(3) . ?
Bi2 I5 3.228(3) . ?
Bi2 I6 3.312(3) . ?
Bi2 I7 2.931(3) . ?
Bi2 I8 2.957(3) . ?
Bi2 I9 2.966(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.50(4) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C2 1.50(4) . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C2 H2F 0.9800 . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C3 1.49(6) . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C3 H3F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Bi1 I2 91.88(8) . . ?
I1 Bi1 I3 95.06(8) . . ?
I1 Bi1 I4 91.59(7) . . ?
I1 Bi1 I5 89.31(8) . . ?
I1 Bi1 I6 174.72(8) . . ?
I2 Bi1 I4 93.58(7) . . ?
I2 Bi1 I5 177.84(8) . . ?
I2 Bi1 I6 91.82(8) . . ?
I3 Bi1 I2 92.26(8) . . ?
I3 Bi1 I4 171.01(7) . . ?
I3 Bi1 I5 89.43(8) . . ?
I3 Bi1 I6 88.56(8) . . ?
I4 Bi1 I6 84.42(6) . . ?
I5 Bi1 I4 84.59(7) . . ?
I5 Bi1 I6 86.88(7) . . ?
I4 Bi2 I6 82.35(7) . . ?
I5 Bi2 I4 82.57(7) . . ?
I5 Bi2 I6 84.16(7) . . ?
I7 Bi2 I4 89.21(7) . . ?
I7 Bi2 I5 91.19(8) . . ?
I7 Bi2 I6 170.82(8) . . ?
I7 Bi2 I8 94.62(8) . . ?
I7 Bi2 I9 91.98(8) . . ?
I8 Bi2 I4 95.27(8) . . ?
I8 Bi2 I5 173.78(8) . . ?
I8 Bi2 I6 89.78(8) . . ?
I8 Bi2 I9 93.28(8) . . ?
I9 Bi2 I4 171.24(8) . . ?
I9 Bi2 I5 88.73(8) . . ?
I9 Bi2 I6 95.83(8) . . ?
Bi1 I4 Bi2 78.82(8) . . ?
Bi1 I5 Bi2 79.64(7) . . ?
Bi1 I6 Bi2 77.28(6) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
N1 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C2 N2 H2A 109.5 . . ?
C2 N2 H2B 109.5 . . ?
C2 N2 H2C 109.5 . . ?
N2 C2 H2D 109.5 . . ?
N2 C2 H2E 109.5 . . ?
N2 C2 H2F 109.5 . . ?
H2D C2 H2E 109.5 . . ?
H2D C2 H2F 109.5 . . ?
H2E C2 H2F 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C3 N3 H3A 109.5 . . ?
C3 N3 H3B 109.5 . . ?
C3 N3 H3C 109.5 . . ?
N3 C3 H3D 109.5 . . ?
N3 C3 H3E 109.5 . . ?
N3 C3 H3F 109.5 . . ?
H3D C3 H3E 109.5 . . ?
H3D C3 H3F 109.5 . . ?
H3E C3 H3F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A I1 0.91 3.33 3.73(3) 109.3 4_566 yes
N1 H1A I2 0.91 2.79 3.65(3) 158.1 4_566 yes
N1 H1B I9 0.91 2.73 3.60(3) 160.6 . yes
N1 H1C I3 0.91 3.05 3.78(3) 138.4 4_566 yes
N1 H1C I8 0.91 3.16 3.84(3) 133.5 . yes
C1 H1D I5 0.98 3.17 3.71(3) 116.5 1_455 yes
C1 H1D I7 0.98 3.26 4.17(3) 153.6 1_455 yes
N2 H2A I6 0.91 3.01 3.88(3) 158.8 . yes
N2 H2B I3 0.91 3.24 3.70(3) 112.9 . yes
N2 H2B I7 0.91 2.95 3.78(3) 152.6 4_565 yes
N2 H2C I1 0.91 2.94 3.72(3) 144.9 1_455 yes
N2 H2C I9 0.91 3.16 3.78(3) 126.6 4_565 yes
C2 H2D I4 0.98 3.28 4.06(4) 138.1 2 yes
C2 H2E I3 0.98 3.29 4.06(4) 136.5 1_455 yes
C2 H2F I8 0.98 3.24 4.18(4) 161.3 2 yes
N3 H3A I7 0.91 3.16 3.81(4) 129.7 . yes
N3 H3B I4 0.91 2.97 3.70(4) 138.4 . yes
N3 H3B I5 0.91 3.20 3.67(3) 114.1 . yes
N3 H3C I6 0.91 3.08 3.85(4) 144.4 1_655 yes
C3 H3D I6 0.98 3.25 4.04(4) 139.8 2_645 yes
C3 H3E I4 0.98 3.22 3.97(5) 134.9 1_655 yes
C3 H3F I9 0.98 3.22 4.08(4) 146.7 2_645 yes

_iucr_refine_instructions_details 
;
TITL cbf_twin1_hklf4_a.res in P2(1)/n
    mbi_100k_4_dimer.res
    created by SHELXL-2018/3 at 19:37:04 on 19-Dec-2018
REM Old TITL cbf_twin1_hklf4 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.251, Rweak 0.026, Alpha 0.125
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C3 N1 I9 Bi2
CELL 0.6804 8.497219 14.686889 21.553773 90 91.6472 90
ZERR 4 0.00029 0.000501 0.0012 0 0.0036 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Bi I N
DISP Bi -3.0839 9.9321 39193.2903
DISP C 0.0031 0.0015 10.5749
DISP I -0.483 1.6974 6920.3567
DISP N 0.0058 0.0029 17.8063
UNIT 12 72 8 36 12
EQIV $1 -0.5+X,0.5-Y,0.5+Z
EQIV $2 -1+X,+Y,+Z
EQIV $3 -0.5+X,0.5-Y,-0.5+Z
EQIV $4 0.5-X,0.5+Y,0.5-Z
EQIV $5 1+X,+Y,+Z
EQIV $6 1.5-X,-0.5+Y,0.5-Z
RIGU $C $N
ISOR 0.01 0.02 C3 N3 N2 C2 C1

L.S. 20
PLAN  10
TEMP -173.15
HTAB N1 I1_$1
HTAB N1 I2_$1
HTAB N1 I9
HTAB N1 I3_$1
HTAB N1 I8
HTAB C1 I5_$2
HTAB C1 I7_$2
HTAB N2 I6
HTAB N2 I3
HTAB N2 I7_$3
HTAB N2 I1_$2
HTAB N2 I9_$3
HTAB C2 I4_$4
HTAB C2 I3_$2
HTAB C2 I8_$4
HTAB N3 I7
HTAB N3 I4
HTAB N3 I5
HTAB N3 I6_$5
HTAB C3 I6_$6
HTAB C3 I4_$5
HTAB C3 I9_$6
BOND $H
CONF
fmap 2
acta
SHEL 999 0.84
OMIT 4 6 5
OMIT -2 14 -1
REM <olex2.extras>
REM <HklSrc "%.\\MBI_100K_4_Dimer.hkl">
REM </olex2.extras>

WGHT    0.200000
BASF   0.21339   0.18762   0.31370
FVAR       0.41627
BI1   3    0.518888    0.165854    0.158256    11.00000    0.01980    0.01857 =
         0.03361    0.00054    0.00217    0.00150
BI2   3    0.483329    0.170463    0.346743    11.00000    0.01926    0.01937 =
         0.03357    0.00032    0.00194   -0.00158
I1    4    0.800596    0.094517    0.096555    11.00000    0.02804    0.03293 =
         0.04363    0.00177    0.01016    0.00700
I2    4    0.301266    0.071755    0.066775    11.00000    0.02809    0.02844 =
         0.04078   -0.00104   -0.00228   -0.00674
I3    4    0.505612    0.340361    0.086060    11.00000    0.03066    0.02504 =
         0.03990    0.00428    0.00165   -0.00105
I4    4    0.521234   -0.000604    0.253544    11.00000    0.03576    0.01882 =
         0.03687    0.00074    0.00380    0.00126
I5    4    0.740813    0.260672    0.258253    11.00000    0.02735    0.03444 =
         0.03646   -0.00222    0.00300   -0.01270
I6    4    0.227626    0.238237    0.237441    11.00000    0.02458    0.03305 =
         0.03839    0.00235    0.00425    0.00862
I7    4    0.732211    0.093270    0.427694    11.00000    0.02914    0.03374 =
         0.03989    0.00058   -0.00212    0.00841
I8    4    0.222952    0.089581    0.416272    11.00000    0.02858    0.03314 =
         0.04199    0.00260    0.00883   -0.00509
I9    4    0.479938    0.342320    0.418966    11.00000    0.03071    0.02445 =
         0.03948   -0.00301    0.00400    0.00281
N1    5    0.070087    0.327775    0.456486    11.00000    0.05439    0.04113 =
         0.03713    0.00426    0.00164   -0.00578
AFIX 137
H1A   2    0.027780    0.363115    0.486415    11.00000   -1.20000
H1B   2    0.170053    0.346619    0.449508    11.00000   -1.20000
H1C   2    0.071747    0.268693    0.469206    11.00000   -1.20000
AFIX   0
C1    1   -0.027827    0.335859    0.397607    11.00000    0.02487    0.05095 =
         0.03494   -0.00305    0.01325   -0.00290
AFIX 137
H1D   2   -0.080169    0.277651    0.388726    11.00000   -1.50000
H1E   2    0.040100    0.351700    0.363245    11.00000   -1.50000
H1F   2   -0.107295    0.383499    0.402436    11.00000   -1.50000
AFIX   0

N2    5    0.083720    0.282273    0.067797    11.00000    0.04601    0.04729 =
         0.05792    0.00112    0.01283    0.01050
AFIX 137
H2A   2    0.142176    0.266188    0.102101    11.00000   -1.20000
H2B   2    0.148886    0.297717    0.036718    11.00000   -1.20000
H2C   2    0.022185    0.234525    0.055442    11.00000   -1.20000
AFIX   0
C2    1   -0.018860    0.362225    0.082882    11.00000    0.05067    0.04095 =
         0.07511   -0.02274    0.00618    0.00306
AFIX 137
H2D   2   -0.042505    0.361084    0.127110    11.00000   -1.50000
H2E   2   -0.117236    0.358839    0.058122    11.00000   -1.50000
H2F   2    0.036299    0.418865    0.073247    11.00000   -1.50000
AFIX   0

N3    5    0.947378    0.042788    0.279110    11.00000    0.06495    0.07774 =
         0.08160    0.00914    0.00923    0.02147
AFIX 137
H3A   2    0.921528    0.015513    0.315332    11.00000   -1.20000
H3B   2    0.858383    0.053460    0.255748    11.00000   -1.20000
H3C   2    0.996996    0.096494    0.287482    11.00000   -1.20000
AFIX   0
C3    1    1.054422   -0.018101    0.244269    11.00000    0.05563    0.05763 =
         0.05796    0.01601    0.00526    0.00871
AFIX 137
H3D   2    1.089561   -0.068374    0.271163    11.00000   -1.50000
H3E   2    1.146018    0.016717    0.231110    11.00000   -1.50000
H3F   2    0.997932   -0.042602    0.207670    11.00000   -1.50000
AFIX   0
HKLF 5




REM  cbf_twin1_hklf4_a.res in P2(1)/n
REM wR2 = 0.2867, GooF = S = 1.211, Restrained GooF = 1.206 for all data
REM R1 = 0.0920 for 3144 Fo > 4sig(Fo) and 0.0989 for all 3917 data
REM 163 parameters refined using 39 restraints

END  
     
WGHT      0.2000      0.0000 

REM Highest difference peak  3.658,  deepest hole -3.373,  1-sigma level  0.901
Q1    1   0.4904  0.1964  0.3456  11.00000  0.05    3.66
Q2    1  -0.0586  0.1796  0.0574  11.00000  0.05    3.54
Q3    1   0.0582  0.3200  0.5283  11.00000  0.05    3.52
Q4    1  -0.0571  0.3233 -0.0262  11.00000  0.05    3.24
Q5    1  -0.0756  0.2599  0.5043  11.00000  0.05    3.09
Q6    1  -0.2885  0.4403  0.0444  11.00000  0.05    3.04
Q7    1  -0.0494  0.1861  0.4253  11.00000  0.05    3.04
Q8    1   0.0696  0.2649 -0.0273  11.00000  0.05    2.98
Q9    1   0.5438  0.1190  0.1571  11.00000  0.05    2.96
Q10   1   0.5634  0.1796  0.1102  11.00000  0.05    2.93

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0920 for 3144 Fo > 4sig(Fo) and 0.0989 for all 5626 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 3.66, deepest hole -3.37
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0989
  REM R1_gt = 0.0920
  REM wR_ref = 0.2867
  REM GOOF = 1.211
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 5626
  REM Reflections_gt = 3144
  REM Parameters = n/a
  REM Hole = -3.37
  REM Peak = 3.66
  REM Flack = n/a
;

####################################################################### 
# 
# 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_Compound_2H_230K
_database_code_depnum_ccdc_archive 'CCDC 1915352'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2020-04-01 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-02-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, 3 (C1 H6 N1)'
_chemical_formula_sum            'C3 H18 Bi2 I9 N3'
_chemical_formula_weight         1656.26
_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 0.0031 0.0015 '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 -3.0839 9.9321 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4830 1.6974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0058 0.0029 '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      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   8.53568(6)
_cell_length_b                   8.53568(6)
_cell_length_c                   21.7298(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1371.08(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5614
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      28.7540
_cell_measurement_theta_min      2.6230
_exptl_absorpt_coefficient_mu    20.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    4.012
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            771
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        24.094
_diffrn_reflns_theta_max         28.764
_diffrn_reflns_theta_min         1.794
_diffrn_ambient_temperature      230.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6804
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                720
_reflns_number_total             771
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00 360.00   0.25    2.00    --    0.00   0.00   0.00 1440
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0738250000
_diffrn_orient_matrix_UB_12      -0.0842216000
_diffrn_orient_matrix_UB_13      -0.0020810000
_diffrn_orient_matrix_UB_21      -0.0036429000
_diffrn_orient_matrix_UB_22      -0.0064973000
_diffrn_orient_matrix_UB_23      0.0312234000
_diffrn_orient_matrix_UB_31      -0.0548708000
_diffrn_orient_matrix_UB_32      0.0365690000
_diffrn_orient_matrix_UB_33      0.0007517000
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.17
_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 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         771
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0187
_refine_ls_restrained_S_all      1.079
_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)+(0.0238P)²+2.6969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0481
_refine_ls_wR_factor_ref         0.0488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C1 = N2-C2
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim C1 \\sim N2 \\sim C2: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Others
 Fixed Sof: N1(0.16667) H1A(0.16667) H1B(0.16667) H1C(0.16667) C1(0.16667)
 H1D(0.16667) H1E(0.16667) H1F(0.16667) N2(0.08333) H2A(0.08333) H2B(0.08333)
 H2C(0.08333) C2(0.08333) H2D(0.08333) H2E(0.08333) H2F(0.08333)
5.a Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), N2(H2A,H2B,H2C), C2(H2D,H2E,H2F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.34465(2) 0.03779(10) Uani 1 6 d S T P . .
I1 I 0.83410(3) 0.66820(6) 0.41899(2) 0.07197(16) Uani 1 2 d S T P . .
I2 I 0.49834(3) 0.50166(3) 0.250000 0.05430(15) Uani 1 4 d S T P . .
N1 N 0.325(6) 0.607(4) 0.4012(10) 0.103(15) Uani 0.1667 1 d D U P A -1
H1A H 0.377944 0.654335 0.364809 0.124 Uiso 0.1667 1 calc R U P A -1
H1B H 0.206171 0.569613 0.398863 0.124 Uiso 0.1667 1 calc R U P A -1
H1C H 0.340105 0.512846 0.410533 0.124 Uiso 0.1667 1 calc R U P A -1
C1 C 0.408(3) 0.746(4) 0.4493(11) 0.085(11) Uani 0.1667 1 d D U P A -1
H1D H 0.410841 0.855530 0.435972 0.127 Uiso 0.1667 1 calc R U P A -1
H1E H 0.530883 0.771279 0.456816 0.127 Uiso 0.1667 1 calc R U P A -1
H1F H 0.338273 0.702300 0.486904 0.127 Uiso 0.1667 1 calc R U P A -1
N2 N 0.929(10) 0.984(13) 0.2861(15) 0.08(2) Uani 0.0833 1 d D U P B -1
H2A H 0.818580 0.888113 0.279659 0.097 Uiso 0.0833 1 calc R U P B -1
H2B H 0.922775 1.086036 0.285734 0.097 Uiso 0.0833 1 calc R U P B -1
H2C H 0.971329 0.972624 0.322834 0.097 Uiso 0.0833 1 calc R U P B -1
C2 C 1.053(14) 0.993(13) 0.2369(13) 0.08(2) Uani 0.0833 1 d D U P B -1
H2D H 1.035745 1.048066 0.200471 0.120 Uiso 0.0833 1 calc R U P B -1
H2E H 1.028185 0.871605 0.227043 0.120 Uiso 0.0833 1 calc R U P B -1
H2F H 1.177510 1.064797 0.250824 0.120 Uiso 0.0833 1 calc R U P B -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 0.03908(12) 0.03908(12) 0.03520(15) 0.000 0.000 0.01954(6)
I1 0.0822(3) 0.0581(3) 0.0676(3) -0.02683(19) -0.01341(10) 0.02904(13)
I2 0.0669(3) 0.0669(3) 0.0536(3) 0.000 0.000 0.0519(3)
N1 0.044(15) 0.14(3) 0.121(14) -0.043(14) -0.026(13) 0.039(18)
C1 0.053(13) 0.13(3) 0.088(13) -0.038(14) -0.006(10) 0.053(13)
N2 0.10(3) 0.07(2) 0.04(3) -0.002(18) -0.01(3) 0.01(4)
C2 0.10(3) 0.07(3) 0.03(4) -0.002(16) 0.00(3) 0.01(4)

_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 2.9558(4) 3_665 ?
Bi1 I1 2.9558(4) . ?
Bi1 I1 2.9558(4) 2_655 ?
Bi1 I2 3.2285(4) 3_665 ?
Bi1 I2 3.2285(4) . ?
Bi1 I2 3.2285(4) 2_655 ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
N1 C1 1.468(10) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 H1F 0.9700 . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N2 H2C 0.9000 . ?
N2 C2 1.480(10) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C2 H2F 0.9700 . ?

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 92.979(15) 3_665 . ?
I1 Bi1 I1 92.979(15) 3_665 2_655 ?
I1 Bi1 I1 92.979(15) . 2_655 ?
I1 Bi1 I2 91.456(8) 3_665 3_665 ?
I1 Bi1 I2 91.456(8) 2_655 . ?
I1 Bi1 I2 173.556(14) 2_655 3_665 ?
I1 Bi1 I2 91.456(8) . 3_665 ?
I1 Bi1 I2 91.457(8) 3_665 2_655 ?
I1 Bi1 I2 91.456(8) . . ?
I1 Bi1 I2 173.556(14) . 2_655 ?
I1 Bi1 I2 91.456(8) 2_655 2_655 ?
I1 Bi1 I2 173.556(14) 3_665 . ?
I2 Bi1 I2 83.756(10) 2_655 . ?
I2 Bi1 I2 83.757(10) 2_655 3_665 ?
I2 Bi1 I2 83.756(10) 3_665 . ?
Bi1 I2 Bi1 79.145(13) . 16_556 ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
N1 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C2 N2 H2A 109.5 . . ?
C2 N2 H2B 109.5 . . ?
C2 N2 H2C 109.5 . . ?
N2 C2 H2D 109.5 . . ?
N2 C2 H2E 109.5 . . ?
N2 C2 H2F 109.5 . . ?
H2D C2 H2E 109.5 . . ?
H2D C2 H2F 109.5 . . ?
H2E C2 H2F 109.5 . . ?

_shelx_res_file                  
;
TITL Compound_2H_230K_1915352.res in P6(3)/mmc
    ff.res
    created by SHELXL-2018/3 at 18:35:09 on 27-Feb-2020
CELL 0.6804 8.535681 8.535681 21.729845 90 90 120
ZERR 2 0.000056 0.000056 0.000206 0 0 0
LATT 1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM -X,-Y,0.5+Z
SYMM +Y,-X+Y,0.5+Z
SYMM -Y+X,+X,0.5+Z
SYMM +Y,+X,-Z
SYMM -Y+X,-Y,-Z
SYMM -X,-X+Y,-Z
SYMM -Y,-X,0.5-Z
SYMM +Y-X,+Y,0.5-Z
SYMM +X,+X-Y,0.5-Z
SFAC C H Bi I N
DISP Bi -3.0839 9.9321 39193.2903
DISP C 0.0031 0.0015 10.5749
DISP H -0 0 0.6223
DISP I -0.483 1.6974 6920.3567
DISP N 0.0058 0.0029 17.8063
UNIT 6 36 4 18 6
SIMU 0.01 0.02 2 N1 > C2
DFIX 1.48 0.01 N1 C1 N2 C2

L.S. 20
PLAN  10
TEMP -43.15
CONF
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\ff.hkl">
REM </olex2.extras>

WGHT    0.023800    2.696900
FVAR       0.41464
BI1   3    0.666667    0.333333    0.344650    10.16667    0.03908    0.03908 =
         0.03520    0.00000    0.00000    0.01954
I1    4    0.834098    0.668195    0.418991    10.50000    0.08220    0.05809 =
         0.06759   -0.02683   -0.01341    0.02904
I2    4    0.498340    0.501660    0.250000    10.25000    0.06694    0.06694 =
         0.05359    0.00000    0.00000    0.05189
PART -1
N1    5    0.325084    0.607252    0.401226    10.16667    0.04398    0.13622 =
         0.12053   -0.04308   -0.02639    0.03885
AFIX 137
H1A   2    0.377944    0.654335    0.364809    10.16667   -1.20000
H1B   2    0.206171    0.569613    0.398863    10.16667   -1.20000
H1C   2    0.340105    0.512846    0.410533    10.16667   -1.20000
AFIX   0
C1    1    0.408332    0.745846    0.449308    10.16667    0.05336    0.12505 =
         0.08779   -0.03827   -0.00648    0.05324
AFIX 137
H1D   2    0.410841    0.855530    0.435972    10.16667   -1.50000
H1E   2    0.530883    0.771279    0.456816    10.16667   -1.50000
H1F   2    0.338273    0.702300    0.486904    10.16667   -1.50000
AFIX   0

N2    5    0.929365    0.984050    0.286098    10.08333    0.09701    0.06797 =
         0.03605   -0.00173   -0.00515    0.00969
AFIX 137
H2A   2    0.818580    0.888113    0.279659    10.08333   -1.20000
H2B   2    0.922775    1.086036    0.285734    10.08333   -1.20000
H2C   2    0.971329    0.972624    0.322834    10.08333   -1.20000
AFIX   0
C2    1    1.053388    0.992891    0.236867    10.08333    0.09620    0.07039 =
         0.03226   -0.00219   -0.00364    0.01039
AFIX 137
H2D   2    1.035745    1.048066    0.200471    10.08333   -1.50000
H2E   2    1.028185    0.871605    0.227043    10.08333   -1.50000
H2F   2    1.177510    1.064797    0.250824    10.08333   -1.50000
AFIX   0
HKLF 4




REM  Compound_2H_230K_1915352.res in P6(3)/mmc
REM wR2 = 0.0488, GooF = S = 1.085, Restrained GooF = 1.079 for all data
REM R1 = 0.0187 for 720 Fo > 4sig(Fo) and 0.0204 for all 771 data
REM 54 parameters refined using 14 restraints

END

WGHT      0.0238      2.6968

REM Highest difference peak  0.561,  deepest hole -0.672,  1-sigma level  0.128
Q1    1   0.3546  0.5490  0.2500  10.50000  0.05    0.56
Q2    1   0.5547  0.4453  0.2500  10.25000  0.05    0.54
Q3    1   0.5165  0.2583  0.3450  10.50000  0.05    0.51
Q4    1   0.2550  0.5100  0.2500  10.25000  0.05    0.51
Q5    1   0.7944  0.5887  0.4282  10.50000  0.05    0.48
Q6    1   0.6136  0.5415  0.2500  10.50000  0.05    0.47
Q7    1   0.3333  0.6667  0.2682  10.16667  0.05    0.45
Q8    1   0.8166  0.5595  0.4258  11.00000  0.05    0.44
Q9    1   0.7978  0.3989  0.3456  10.50000  0.05    0.42
Q10   1   0.7591  0.5183  0.2500  10.25000  0.05    0.42
;
_shelx_res_checksum              96664
_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_compound_2_293K
_database_code_depnum_ccdc_archive 'CCDC 1915353'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2020-04-01 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-03-01
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, 3 (C1 H6 N1)'
_chemical_formula_sum            'C3 H18 Bi2 I9 N3'
_chemical_formula_weight         1656.26
_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 0.0031 0.0015 '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 -3.0839 9.9321 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4830 1.6974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0058 0.0029 '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      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   8.57310(10)
_cell_length_b                   8.57310(10)
_cell_length_c                   21.7479(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1384.28(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3646
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      27.8620
_cell_measurement_theta_min      2.6160
_exptl_absorpt_coefficient_mu    20.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    3.974
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11836
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        24.094
_diffrn_reflns_theta_max         28.539
_diffrn_reflns_theta_min         1.793
_diffrn_ambient_temperature      293(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6804
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                703
_reflns_number_total             767
_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 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         767
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.054
_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)+(0.0206P)²+3.6640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C1 = N2-C2
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim C1 \\sim N2 \\sim C2: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Others
 Fixed Sof: N1(0.16667) H1A(0.16667) H1B(0.16667) H1C(0.16667) C1(0.16667)
 H1D(0.16667) H1E(0.16667) H1F(0.16667) N2(0.08333) H2A(0.08333) H2B(0.08333)
 H2C(0.08333) C2(0.08333) H2D(0.08333) H2E(0.08333) H2F(0.08333)
5.a Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), N2(H2A,H2B,H2C), C2(H2D,H2E,H2F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.34493(2) 0.03984(11) Uani 1 6 d S T P . .
I1 I 0.83370(3) 0.66741(6) 0.41875(2) 0.07578(17) Uani 1 2 d S T P . .
I2 I 0.49860(4) 0.50140(4) 0.250000 0.05843(17) Uani 1 4 d S T P . .
N1 N 0.325(6) 0.607(4) 0.4010(12) 0.108(14) Uani 0.1667 1 d D U P A -1
H1A H 0.385237 0.641949 0.365783 0.130 Uiso 0.1667 1 calc R U P A -1
H1B H 0.211446 0.580691 0.394829 0.130 Uiso 0.1667 1 calc R U P A -1
H1C H 0.325101 0.509142 0.414815 0.130 Uiso 0.1667 1 calc R U P A -1
C1 C 0.410(4) 0.752(5) 0.4467(14) 0.096(12) Uani 0.1667 1 d D U P A -1
H1D H 0.480524 0.865088 0.425932 0.145 Uiso 0.1667 1 calc R U P A -1
H1E H 0.487058 0.729770 0.472906 0.145 Uiso 0.1667 1 calc R U P A -1
H1F H 0.318997 0.756337 0.471027 0.145 Uiso 0.1667 1 calc R U P A -1
N2 N 1.052(17) 0.994(15) 0.2858(18) 0.10(2) Uani 0.0833 1 d D U P B -1
H2A H 1.164411 1.055974 0.271387 0.121 Uiso 0.0833 1 calc R U P B -1
H2B H 1.026361 0.881788 0.294328 0.121 Uiso 0.0833 1 calc R U P B -1
H2C H 1.043014 1.046154 0.319823 0.121 Uiso 0.0833 1 calc R U P B -1
C2 C 0.925(14) 0.990(13) 0.239(2) 0.10(2) Uani 0.0833 1 d D U P B -1
H2D H 0.937324 1.106876 0.235664 0.150 Uiso 0.0833 1 calc R U P B -1
H2E H 0.804251 0.903671 0.250819 0.150 Uiso 0.0833 1 calc R U P B -1
H2F H 0.951658 0.955736 0.199918 0.150 Uiso 0.0833 1 calc R U P B -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 0.04092(13) 0.04092(13) 0.03769(16) 0.000 0.000 0.02046(7)
I1 0.0865(3) 0.0595(3) 0.0723(3) -0.0273(2) -0.01366(11) 0.02974(14)
I2 0.0714(3) 0.0714(3) 0.0587(3) 0.000 0.000 0.0554(3)
N1 0.039(17) 0.14(3) 0.15(2) -0.044(17) -0.025(15) 0.048(19)
C1 0.050(14) 0.13(3) 0.12(2) -0.050(19) -0.019(13) 0.056(15)
N2 0.14(7) 0.06(3) 0.07(3) 0.02(3) 0.05(4) 0.03(6)
C2 0.14(7) 0.07(3) 0.07(4) 0.02(3) 0.05(5) 0.04(6)

_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 2.9546(4) 3_665 ?
Bi1 I1 2.9546(4) 2_655 ?
Bi1 I1 2.9546(4) . ?
Bi1 I2 3.2388(5) 3_665 ?
Bi1 I2 3.2388(5) . ?
Bi1 I2 3.2388(5) 2_655 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.472(10) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C2 1.480(10) . ?
C2 H2D 0.9600 . ?
C2 H2E 0.9600 . ?
C2 H2F 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 I1 93.275(16) 3_665 2_655 ?
I1 Bi1 I1 93.274(16) 3_665 . ?
I1 Bi1 I1 93.274(16) 2_655 . ?
I1 Bi1 I2 91.314(9) 3_665 3_665 ?
I1 Bi1 I2 91.314(9) . . ?
I1 Bi1 I2 91.314(9) . 3_665 ?
I1 Bi1 I2 173.315(15) 2_655 3_665 ?
I1 Bi1 I2 91.314(9) 3_665 2_655 ?
I1 Bi1 I2 91.313(9) 2_655 . ?
I1 Bi1 I2 91.313(9) 2_655 2_655 ?
I1 Bi1 I2 173.316(15) . 2_655 ?
I1 Bi1 I2 173.315(15) 3_665 . ?
I2 Bi1 I2 83.717(11) 2_655 . ?
I2 Bi1 I2 83.718(11) 2_655 3_665 ?
I2 Bi1 I2 83.717(11) 3_665 . ?
Bi1 I2 Bi1 79.198(15) . 16_556 ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
N1 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C2 N2 H2A 109.5 . . ?
C2 N2 H2B 109.5 . . ?
C2 N2 H2C 109.5 . . ?
N2 C2 H2D 109.5 . . ?
N2 C2 H2E 109.5 . . ?
N2 C2 H2F 109.5 . . ?
H2D C2 H2E 109.5 . . ?
H2D C2 H2F 109.5 . . ?
H2E C2 H2F 109.5 . . ?

_shelx_res_file                  
;
TITL Compound_2_293K.res in P6(3)/mmc
    compound_2_293k.res
    created by SHELXL-2018/3 at 17:21:43 on 01-Mar-2020
CELL 0.6804 8.5731 8.5731 21.7479 90 90 120
ZERR 2 0.0001 0.0001 0.0003 0 0 0
LATT 1
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM -X,-Y,0.5+Z
SYMM +Y,-X+Y,0.5+Z
SYMM -Y+X,+X,0.5+Z
SYMM +Y,+X,-Z
SYMM -Y+X,-Y,-Z
SYMM -X,-X+Y,-Z
SYMM -Y,-X,0.5-Z
SYMM +Y-X,+Y,0.5-Z
SYMM +X,+X-Y,0.5-Z
SFAC C H Bi I N
DISP Bi -3.0839 9.9321 39193.2903
DISP C 0.0031 0.0015 10.5749
DISP H -0 0 0.6223
DISP I -0.483 1.6974 6920.3567
DISP N 0.0058 0.0029 17.8063
UNIT 6 36 4 18 6
DFIX 1.48 0.01 N1 C1 N2 C2
SIMU 0.01 0.02 2 N1 > C2

L.S. 20
PLAN  2
TEMP 19.85
CONF
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\Compound_2_293K.hkl">
REM </olex2.extras>

WGHT    0.020600    3.664000
FVAR       0.40803
BI1   3    0.666667    0.333333    0.344926    10.16667    0.04092    0.04092 =
         0.03769    0.00000    0.00000    0.02046
I1    4    0.833703    0.667405    0.418749    10.50000    0.08651    0.05949 =
         0.07233   -0.02732   -0.01366    0.02974
I2    4    0.498602    0.501398    0.250000    10.25000    0.07142    0.07142 =
         0.05867    0.00000    0.00000    0.05538
PART -1
N1    5    0.324535    0.606591    0.401016    10.16667    0.03858    0.13941 =
         0.15193   -0.04446   -0.02474    0.04794
AFIX 137
H1A   2    0.385237    0.641949    0.365783    10.16667   -1.20000
H1B   2    0.211446    0.580691    0.394829    10.16667   -1.20000
H1C   2    0.325101    0.509142    0.414815    10.16667   -1.20000
AFIX   0
C1    1    0.410227    0.752095    0.446691    10.16667    0.04995    0.13133 =
         0.12232   -0.04995   -0.01866    0.05603
AFIX 137
H1D   2    0.480524    0.865088    0.425932    10.16667   -1.50000
H1E   2    0.487058    0.729770    0.472906    10.16667   -1.50000
H1F   2    0.318997    0.756337    0.471027    10.16667   -1.50000
AFIX   0

N2    5    1.052431    0.993807    0.285786    10.08333    0.14269    0.06482 =
         0.06977    0.01823    0.04632    0.03333
AFIX 137
H2A   2    1.164411    1.055974    0.271387    10.08333   -1.20000
H2B   2    1.026361    0.881788    0.294328    10.08333   -1.20000
H2C   2    1.043014    1.046154    0.319823    10.08333   -1.20000
AFIX   0
C2    1    0.925248    0.989658    0.238933    10.08333    0.14293    0.06563 =
         0.06895    0.01661    0.04833    0.03523
AFIX 137
H2D   2    0.937324    1.106876    0.235664    10.08333   -1.50000
H2E   2    0.804251    0.903671    0.250819    10.08333   -1.50000
H2F   2    0.951658    0.955736    0.199918    10.08333   -1.50000
AFIX   0
HKLF 4




REM  Compound_2_293K.res in P6(3)/mmc
REM wR2 = 0.0506, GooF = S = 1.062, Restrained GooF = 1.054 for all data
REM R1 = 0.0203 for 703 Fo > 4sig(Fo) and 0.0223 for all 767 data
REM 54 parameters refined using 14 restraints

END

WGHT      0.0206      3.6638

REM Highest difference peak  0.462,  deepest hole -0.736,  1-sigma level  0.111
Q1    1   0.7009  0.4017  0.3946  10.50000  0.05    0.46
Q2    1   0.4258  0.5742  0.2500  10.25000  0.05    0.45
;
_shelx_res_checksum              83210
_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_Compound_1_100K
_database_code_depnum_ccdc_archive 'CCDC 1915351'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;Institute of Chemical Sciences and Engineering, Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2020-04-01 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2018-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi I6, 6(C H6 N), 3(Cl)'
_chemical_formula_sum            'C6 H36 Bi Cl3 I6 N6'
_chemical_formula_weight         1269.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H36 Bi Cl3 I6 N6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0032 0.0015 '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 -3.4385 10.2164 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1432 0.1527 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4515 1.7554 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0031 '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           67
_space_group_name_H-M_alt        'C m m e'
_space_group_name_Hall           '-C 2b 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z'
'x, -y, -z'
'-x, y+1/2, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z'
'-x, -y, -z'
'x, y-1/2, -z'
'-x, y, z'
'x, -y-1/2, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z'
'-x+1/2, y+1/2, z'
'x+1/2, -y, z'

_cell_length_a                   18.94284(14)
_cell_length_b                   18.83413(12)
_cell_length_c                   9.13917(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3260.60(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10292
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      32.1830
_cell_measurement_theta_min      2.0800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2264
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7614
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.589
_diffrn_reflns_theta_max         25.683
_diffrn_reflns_theta_min         2.098
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 360.00   1.00    6.99   0.00   0.00   0.00    --   360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0291114000
_diffrn_orient_matrix_UB_12      -0.0187337000
_diffrn_orient_matrix_UB_13      0.0250642000
_diffrn_orient_matrix_UB_21      0.0043463000
_diffrn_orient_matrix_UB_22      -0.0244030000
_diffrn_orient_matrix_UB_23      -0.0560252000
_diffrn_orient_matrix_UB_31      0.0218116000
_diffrn_orient_matrix_UB_32      -0.0201852000
_diffrn_orient_matrix_UB_33      0.0446260000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6935
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1751
_reflns_number_total             1751
_reflns_odcompleteness_completeness 98.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.69
_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 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         1.044
_refine_diff_density_min         -1.387
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       0.000174(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1751
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0217
_refine_ls_restrained_S_all      1.114
_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)+(0.0292P)²+30.8967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0589
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 N2-H2B = N2-H2A
 0.89 with sigma of 0.01
 C2-H2C = C2-H2D
 0.98 with sigma of 0.01
 H2A-H2B
 1.453 with sigma of 0.01
 H2C-H2D
 1.6 with sigma of 0.01
 N2-H2D
 2.031 with sigma of 0.01
 N2-H2C
 2.031 with sigma of 0.01
 C2-H2B
 1.981 with sigma of 0.01
 C2-H2A
 1.981 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.750000 0.71708(3) 0.01463(11) Uani 1 4 d S T P . .
I1 I 0.500000 0.58809(2) 0.69571(5) 0.02111(12) Uani 1 2 d S T P . .
I2 I 0.39155(2) 0.750000 0.97369(4) 0.01859(12) Uani 1 2 d S T P . .
I3 I 0.37457(2) 0.750000 0.50698(4) 0.01939(12) Uani 1 2 d S T P . .
Cl1 Cl 0.250000 0.500000 0.500000 0.0285(5) Uani 1 4 d S T P . .
Cl2 Cl 0.36508(8) 0.500000 0.000000 0.0189(3) Uani 1 2 d S T P . .
N1 N 0.3112(2) 0.6012(2) 0.7410(4) 0.0245(8) Uani 1 1 d . . . . .
H1A H 0.303556 0.567655 0.671163 0.029 Uiso 1 1 calc GR . . . .
H1B H 0.332199 0.580812 0.820089 0.029 Uiso 1 1 calc GR . . . .
H1C H 0.339914 0.635689 0.704360 0.029 Uiso 1 1 calc GR . . . .
C1 C 0.2430(3) 0.6330(3) 0.7855(6) 0.0295(11) Uani 1 1 d . . . . .
H1D H 0.218640 0.651580 0.698909 0.044 Uiso 1 1 calc GR . . . .
H1E H 0.251576 0.671808 0.854679 0.044 Uiso 1 1 calc GR . . . .
H1F H 0.213586 0.596703 0.832187 0.044 Uiso 1 1 calc GR . . . .
N2 N 0.500000 0.4059(3) 0.8988(6) 0.0203(11) Uani 1 2 d DS T P . .
H2A H 0.500000 0.3683(9) 0.9578(15) 0.024 Uiso 1 2 d DRS T P . .
H2B H 0.5370(13) 0.4330(14) 0.9177(17) 0.024 Uiso 1 1 d DR . . . .
C2 C 0.500000 0.3823(5) 0.7432(8) 0.0388(19) Uani 1 2 d DS T P . .
H2C H 0.500000 0.4247(11) 0.6803(15) 0.058 Uiso 1 2 d DRS T P . .
H2D H 0.5431(14) 0.3551(16) 0.7244(18) 0.058 Uiso 1 1 d DR . . . .

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 0.01453(17) 0.01419(17) 0.01515(17) 0.000 0.000 0.000
I1 0.0216(2) 0.0181(2) 0.0237(2) 0.00150(15) 0.000 0.000
I2 0.0171(2) 0.0203(2) 0.0183(2) 0.000 0.00283(14) 0.000
I3 0.0208(2) 0.0197(2) 0.0177(2) 0.000 -0.00463(15) 0.000
Cl1 0.0456(14) 0.0233(10) 0.0167(10) 0.000 0.000 0.000
Cl2 0.0196(7) 0.0183(6) 0.0187(7) 0.0033(5) 0.000 0.000
N1 0.022(2) 0.025(2) 0.026(2) 0.0010(16) -0.0024(16) -0.0024(17)
C1 0.024(3) 0.034(3) 0.030(3) 0.000(2) -0.0004(19) 0.001(2)
N2 0.021(3) 0.020(3) 0.020(3) 0.000(2) 0.000 0.000
C2 0.053(5) 0.036(5) 0.028(4) -0.015(3) 0.000 0.000

_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 3.0557(4) . ?
Bi1 I1 3.0557(4) 2_665 ?
Bi1 I2 3.1178(4) 2_665 ?
Bi1 I2 3.1177(4) . ?
Bi1 I3 3.0550(4) . ?
Bi1 I3 3.0549(4) 2_665 ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.482(7) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
N2 H2A 0.891(10) . ?
N2 H2B 0.883(9) . ?
N2 H2B 0.883(9) 11_655 ?
N2 C2 1.490(9) . ?
C2 H2C 0.985(10) . ?
C2 H2D 0.979(10) . ?
C2 H2D 0.979(10) 11_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
I1 Bi1 I1 172.668(19) . 2_665 ?
I1 Bi1 I2 92.757(7) . 2_665 ?
I1 Bi1 I2 92.757(7) 2_665 2_665 ?
I1 Bi1 I2 92.757(7) 2_665 . ?
I1 Bi1 I2 92.757(7) . . ?
I2 Bi1 I2 82.437(16) . 2_665 ?
I3 Bi1 I1 87.697(6) . 2_665 ?
I3 Bi1 I1 87.697(6) 2_665 2_665 ?
I3 Bi1 I1 87.697(6) . . ?
I3 Bi1 I1 87.697(6) 2_665 . ?
I3 Bi1 I2 170.162(14) 2_665 . ?
I3 Bi1 I2 170.162(14) . 2_665 ?
I3 Bi1 I2 87.725(11) 2_665 2_665 ?
I3 Bi1 I2 87.724(11) . . ?
I3 Bi1 I3 102.113(18) 2_665 . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
N1 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
H2A N2 H2B 110.0(15) . 11_655 ?
H2A N2 H2B 110.0(15) . . ?
H2B N2 H2B 105(4) . 11_655 ?
C2 N2 H2A 109.8(12) . . ?
C2 N2 H2B 111.1(12) . . ?
C2 N2 H2B 111.1(12) . 11_655 ?
N2 C2 H2C 108.3(12) . . ?
N2 C2 H2D 108.9(12) . 11_655 ?
N2 C2 H2D 108.9(12) . . ?
H2C C2 H2D 108.8(15) . . ?
H2C C2 H2D 108.8(14) . 11_655 ?
H2D C2 H2D 113(4) . 11_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl1 0.91 2.26 3.135(4) 161.7 . yes
N1 H1B Cl2 0.91 2.33 3.206(4) 162.8 1_556 yes
N1 H1C I1 0.91 3.16 3.608(4) 112.3 . yes
N1 H1C I3 0.91 2.88 3.723(4) 153.9 . yes
C1 H1D I3 0.98 3.18 4.118(5) 161.4 8_546 yes
C1 H1E I2 0.98 3.22 3.967(6) 134.1 . yes
C1 H1F Cl2 0.98 2.81 3.783(6) 172.7 6_556 yes
N2 H2A I1 0.891(10) 3.272(17) 3.708(5) 112.7(15) 3_567 yes
N2 H2A I2 0.891(10) 3.094(11) 3.769(5) 134.1(5) 4_647 yes
N2 H2A I2 0.891(10) 3.094(11) 3.769(5) 134.1(5) 3_567 yes
N2 H2B Cl2 0.883(9) 2.367(10) 3.244(4) 172.5(15) 9_666 yes
C2 H2C I1 0.985(10) 3.08(2) 3.901(9) 141.7(15) . yes
C2 H2D I3 0.979(10) 3.290(11) 4.133(6) 145.4(18) 4_646 yes

_iucr_refine_instructions_details 
;
TITL shelx A b m 2 R = 0.03 New:Cmma
    bi_mono_cl.res
    created by SHELXL-2018/3 at 18:58:12 on 11-Dec-2018
CELL 0.6935 18.942835 18.834133 9.139174 90 90 90
ZERR 4 0.000138 0.00012 0.000062 0 0 0
LATT 7
SYMM -X,0.5-Y,+Z
SYMM +X,-Y,-Z
SYMM -X,0.5+Y,-Z
SFAC C H Bi Cl I N
DISP Bi -3.4385 10.2164 41148.6496
DISP C 0.0032 0.0015 10.9913
DISP Cl 0.1432 0.1527 635.8497
DISP H -0 0 0.623
DISP I -0.4515 1.7554 7284.0264
DISP N 0.0061 0.0031 18.6139
UNIT 24 144 4 12 24 24
EQIV $1 +X,+Y,1+Z
EQIV $2 0.5-X,1-Y,1+Z
EQIV $3 1-X,1-Y,1-Z
EQIV $4 1-X,-0.5+Y,1-Z
EQIV $5 0.5-X,+Y,1-Z
EQIV $6 +X,1-Y,2-Z
EQIV $7 1-X,-0.5+Y,2-Z
DFIX 0.89 0.01 N2 H2b N2 H2a
DFIX 0.98 0.01 C2 H2c C2 H2d
DANG 1.453 0.01 H2a H2b
DANG 1.6 0.01 H2c H2d
DANG 2.031 0.01 N2 H2d
DANG 2.031 0.01 N2 H2c
DANG 1.981 0.01 C2 H2b
DANG 1.981 0.01 C2 H2a

L.S. 20
PLAN  -10
TEMP -173.15
HTAB N1 Cl1
HTAB N1 Cl2_$1
HTAB N1 I1
HTAB N1 I3
HTAB C1 I3_$5
HTAB C1 I2
HTAB C1 Cl2_$2
HTAB N2 I1_$6
HTAB N2 I2_$7
HTAB N2 I2_$6
HTAB N2 Cl2_$3
HTAB C2 I1
HTAB C2 I3_$4
BOND $H
CONF
fmap 2
acta
SHEL 999 0.8
REM <olex2.extras>
REM <HklSrc "%.\\Bi_Mono_Cl.hkl">
REM </olex2.extras>

WGHT    0.029200   30.896700
EXTI    0.000174
FVAR       0.83436
BI1   3    0.500000    0.750000    0.717084    10.25000    0.01453    0.01419 =
         0.01515    0.00000    0.00000    0.00000
I1    5    0.500000    0.588089    0.695706    10.50000    0.02163    0.01805 =
         0.02366    0.00150    0.00000    0.00000
I2    5    0.391548    0.750000    0.973691    10.50000    0.01709    0.02035 =
         0.01832    0.00000    0.00283    0.00000
I3    5    0.374567    0.750000    0.506979    10.50000    0.02076    0.01968 =
         0.01771    0.00000   -0.00463    0.00000
CL1   4    0.250000    0.500000    0.500000    10.25000    0.04560    0.02325 =
         0.01674    0.00000    0.00000    0.00000
CL2   4    0.365080    0.500000    0.000000    10.50000    0.01957    0.01831 =
         0.01870    0.00326    0.00000    0.00000
N1    6    0.311250    0.601227    0.740975    11.00000    0.02242    0.02451 =
         0.02648    0.00098   -0.00238   -0.00235
AFIX 137
H1A   2    0.303556    0.567655    0.671163    11.00000   -1.20000
H1B   2    0.332199    0.580812    0.820089    11.00000   -1.20000
H1C   2    0.339914    0.635689    0.704360    11.00000   -1.20000
AFIX   0
C1    1    0.242982    0.633022    0.785454    11.00000    0.02431    0.03398 =
         0.03007   -0.00009   -0.00035    0.00105
AFIX 137
H1D   2    0.218640    0.651580    0.698909    11.00000   -1.50000
H1E   2    0.251576    0.671808    0.854679    11.00000   -1.50000
H1F   2    0.213586    0.596703    0.832187    11.00000   -1.50000
AFIX   0

N2    6    0.500000    0.405943    0.898803    10.50000    0.02079    0.01999 =
         0.02015   -0.00014    0.00000    0.00000
H2A   2    0.500000    0.368255    0.957800    10.50000   -1.20000
H2B   2    0.536956    0.432998    0.917699    11.00000   -1.20000
C2    1    0.500000    0.382277    0.743231    10.50000    0.05280    0.03604 =
         0.02768   -0.01507    0.00000    0.00000
H2C   2    0.500000    0.424720    0.680346    10.50000   -1.50000
H2D   2    0.543111    0.355080    0.724429    11.00000   -1.50000
HKLF 4




REM  shelx A b m 2 R = 0.03 New:Cmma
REM wR2 = 0.0589, GooF = S = 1.117, Restrained GooF = 1.114 for all data
REM R1 = 0.0217 for 1751 Fo > 4sig(Fo) and 0.0217 for all 1751 data
REM 74 parameters refined using 10 restraints

END  
     
WGHT      0.0292     30.8834 

REM Highest difference peak  1.044,  deepest hole -1.387,  1-sigma level  0.170
Q1    1   0.5000  0.8801  0.7719  10.50000  0.05    1.04
Q2    1   0.4009  0.7500  1.0469  10.50000  0.05    0.77
Q3    1   0.5000  0.7500  1.1889  10.25000  0.05    0.75
Q4    1   0.5153  0.7500  0.6548  10.50000  0.05    0.73
Q5    1   0.5097  0.7500  0.7784  10.50000  0.05    0.73
Q6    1   0.5000  0.7989  0.7062  10.50000  0.05    0.61
Q7    1   0.5000  0.5704  0.8124  10.50000  0.05    0.58
Q8    1   0.2614  0.7500  0.6375  10.50000  0.05    0.57
Q9    1   0.5000  0.7500  1.1128  10.25000  0.05    0.54
Q10   1   0.5000  0.5247  0.5135  10.50000  0.05    0.53

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0217 for 1751 Fo > 4sig(Fo) and 0.0217 for all 11517 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 1.04, deepest hole -1.39
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0217
  REM R1_gt = 0.0217
  REM wR_ref = 0.0589
  REM GOOF = 1.117
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 11517
  REM Reflections_gt = 1751
  REM Parameters = n/a
  REM Hole = -1.39
  REM Peak = 1.04
  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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.647
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
