# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound1
_database_code_depnum_ccdc_archive 'CCDC 1939881'
loop_
_audit_author_name
_audit_author_address
'Johanna Heine'
;University of Marburg
Germany
;
_audit_update_record             
;
2019-07-11 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2019-06-24
_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         'Bi2 I7, C5 H12 N'
_chemical_formula_sum            'C5 H12 Bi2 I7 N'
_chemical_formula_weight         1392.42
_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   14.4647(8)
_cell_length_b                   7.5084(4)
_cell_length_c                   20.9965(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.165(2)
_cell_angle_gamma                90
_cell_volume                     2166.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.421
_shelx_estimated_absorpt_T_min   0.235
_exptl_absorpt_coefficient_mu    26.177
_exptl_absorpt_correction_T_max  0.3311
_exptl_absorpt_correction_T_min  0.2865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1022 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.8653. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    4.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2344
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            83909
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.322
_diffrn_reflns_theta_min         2.713
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3402
_reflns_number_total             3936
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.912
_refine_diff_density_min         -1.257
_refine_diff_density_rms         0.217
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0130P)²+4.8387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0352
_refine_ls_wR_factor_ref         0.0367
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Shared sites
{C5, N5}
{C6, N6}
3. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(N5)
Uanis(C6) = Uanis(N6)
4. Others
 Sof(C5)=Sof(N6)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=
 Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=1-FVAR(1)
 Sof(N5)=Sof(C6)=Sof(H1BD)=Sof(H1BE)=Sof(H1BF)=Sof(H4BD)=Sof(H4BE)=Sof(H4BF)=
 Sof(H2BD)=Sof(H2BE)=Sof(H2BF)=Sof(H3BD)=Sof(H3BE)=Sof(H3BF)=FVAR(1)
5.a Idealised Me refined as rotating group:
 C1(H1BD,H1BE,H1BF), C1(H1AA,H1AB,H1AC), C4(H4AA,H4AB,H4AC), C4(H4BD,H4BE,
 H4BF), C2(H2BD,H2BE,H2BF), C2(H2AA,H2AB,H2AC), C3(H3AA,H3AB,H3AC), C3(H3BD,
 H3BE,H3BF)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Bi2 Bi 0.45006(2) 0.76583(3) 0.79002(2) 0.00852(6) Uani 1 1 d . . . . .
Bi1 Bi 0.55027(2) 0.28542(3) 0.71618(2) 0.00819(6) Uani 1 1 d . . . . .
I8 I 0.2500 0.95536(7) 0.7500 0.01150(12) Uani 1 2 d S T P . .
I4 I 0.65179(3) 0.61065(5) 0.80578(2) 0.01175(9) Uani 1 1 d . . . . .
I2 I 0.46648(3) -0.05474(5) 0.64850(2) 0.01102(9) Uani 1 1 d . . . . .
I5 I 0.34920(3) 0.44192(5) 0.69876(2) 0.01150(9) Uani 1 1 d . . . . .
I1 I 0.7500 0.09525(7) 0.7500 0.01357(12) Uani 1 2 d S T P . .
I7 I 0.53306(3) 1.10561(5) 0.85814(2) 0.01144(9) Uani 1 1 d . . . . .
I6 I 0.44237(3) 0.60798(5) 0.91384(2) 0.01468(9) Uani 1 1 d . . . . .
I3 I 0.55484(3) 0.44260(5) 0.59164(2) 0.01449(9) Uani 1 1 d . . . . .
N5 N 0.2347(4) 0.1244(7) 0.5121(3) 0.0139(14) Uani 0.53(4) 1 d . . . A 2
C5 C 0.2347(4) 0.1244(7) 0.5121(3) 0.0139(14) Uani 0.47(4) 1 d . . . A 1
N6 N 0.2769(4) 0.0024(8) 0.4885(3) 0.0176(15) Uani 0.47(4) 1 d . . . A 1
C6 C 0.2769(4) 0.0024(8) 0.4885(3) 0.0176(15) Uani 0.53(4) 1 d . . . A 2
C1 C 0.2509(5) 0.3174(8) 0.5031(3) 0.0184(14) Uani 1 1 d . . . . .
H1BD H 0.2974 0.3313 0.4780 0.028 Uiso 0.53(4) 1 calc GR . . A 2
H1BE H 0.2769 0.3742 0.5471 0.028 Uiso 0.53(4) 1 calc GR . . A 2
H1BF H 0.1890 0.3736 0.4782 0.028 Uiso 0.53(4) 1 calc GR . . A 2
H1AA H 0.3172 0.3499 0.5300 0.028 Uiso 0.47(4) 1 calc GR . . A 1
H1AB H 0.2041 0.3877 0.5177 0.028 Uiso 0.47(4) 1 calc GR . . A 1
H1AC H 0.2420 0.3415 0.4557 0.028 Uiso 0.47(4) 1 calc GR . . A 1
C4 C 0.2622(5) -0.1901(8) 0.4973(3) 0.0246(16) Uani 1 1 d . . . . .
H4AA H 0.3139 -0.2343 0.5364 0.037 Uiso 0.47(4) 1 calc GR . . A 1
H4AB H 0.2642 -0.2549 0.4572 0.037 Uiso 0.47(4) 1 calc GR . . A 1
H4AC H 0.1989 -0.2086 0.5041 0.037 Uiso 0.47(4) 1 calc GR . . A 1
H4BD H 0.2281 -0.2063 0.5305 0.037 Uiso 0.53(4) 1 calc GR . . A 2
H4BE H 0.3255 -0.2500 0.5127 0.037 Uiso 0.53(4) 1 calc GR . . A 2
H4BF H 0.2233 -0.2415 0.4544 0.037 Uiso 0.53(4) 1 calc GR . . A 2
C2 C 0.1688(5) 0.0846(9) 0.5522(3) 0.0227(15) Uani 1 1 d . . . . .
H2BD H 0.2069 0.0384 0.5962 0.034 Uiso 0.53(4) 1 calc GR . . A 2
H2BE H 0.1208 -0.0047 0.5288 0.034 Uiso 0.53(4) 1 calc GR . . A 2
H2BF H 0.1352 0.1937 0.5580 0.034 Uiso 0.53(4) 1 calc GR . . A 2
H2AA H 0.1864 0.1593 0.5924 0.034 Uiso 0.47(4) 1 calc GR . . A 1
H2AB H 0.1751 -0.0412 0.5653 0.034 Uiso 0.47(4) 1 calc GR . . A 1
H2AC H 0.1014 0.1093 0.5252 0.034 Uiso 0.47(4) 1 calc GR . . A 1
C3 C 0.3464(5) 0.0482(9) 0.4501(3) 0.0241(16) Uani 1 1 d . . . . .
H3AA H 0.4049 0.1038 0.4804 0.036 Uiso 0.47(4) 1 calc GR . . A 1
H3AB H 0.3148 0.1311 0.4138 0.036 Uiso 0.47(4) 1 calc GR . . A 1
H3AC H 0.3645 -0.0607 0.4312 0.036 Uiso 0.47(4) 1 calc GR . . A 1
H3BD H 0.3919 -0.0506 0.4535 0.036 Uiso 0.53(4) 1 calc GR . . A 2
H3BE H 0.3827 0.1561 0.4690 0.036 Uiso 0.53(4) 1 calc GR . . A 2
H3BF H 0.3096 0.0688 0.4029 0.036 Uiso 0.53(4) 1 calc GR . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi2 I8 3.0966(3) . ?
Bi2 I4 3.0626(5) . ?
Bi2 I2 3.3375(4) 1_565 ?
Bi2 I5 3.1577(4) . ?
Bi2 I7 2.9875(4) . ?
Bi2 I6 2.8907(4) . ?
Bi1 I4 3.1522(4) . ?
Bi1 I2 2.9896(4) . ?
Bi1 I5 3.0512(5) . ?
Bi1 I1 3.1001(4) . ?
Bi1 I7 3.3513(4) 1_545 ?
Bi1 I3 2.8885(4) . ?
I8 Bi2 3.0966(3) 2_556 ?
I2 Bi2 3.3377(4) 1_545 ?
I1 Bi1 3.1001(3) 2_656 ?
I7 Bi1 3.3513(4) 1_565 ?
N5 C6 1.283(7) . ?
N5 C1 1.489(8) . ?
N5 C2 1.486(8) . ?
C5 N6 1.283(7) . ?
C5 C1 1.489(8) . ?
C5 C2 1.486(8) . ?
N6 C4 1.481(8) . ?
N6 C3 1.510(8) . ?
C6 C4 1.481(8) . ?
C6 C3 1.510(8) . ?

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
I8 Bi2 I2 83.846(9) . 1_565 ?
I8 Bi2 I5 88.478(12) . . ?
I4 Bi2 I8 169.250(11) . . ?
I4 Bi2 I2 85.409(11) . 1_565 ?
I4 Bi2 I5 90.971(11) . . ?
I5 Bi2 I2 85.318(11) . 1_565 ?
I7 Bi2 I8 86.535(12) . . ?
I7 Bi2 I4 92.634(12) . . ?
I7 Bi2 I2 87.250(11) . 1_565 ?
I7 Bi2 I5 171.454(12) . . ?
I6 Bi2 I8 97.917(11) . . ?
I6 Bi2 I4 92.825(12) . . ?
I6 Bi2 I2 178.182(13) . 1_565 ?
I6 Bi2 I5 95.157(13) . . ?
I6 Bi2 I7 92.402(12) . . ?
I4 Bi1 I7 86.057(11) . 1_545 ?
I2 Bi1 I4 171.855(12) . . ?
I2 Bi1 I5 92.408(12) . . ?
I2 Bi1 I1 85.764(12) . . ?
I2 Bi1 I7 86.966(11) . 1_545 ?
I5 Bi1 I4 91.288(11) . . ?
I5 Bi1 I1 171.991(11) . . ?
I5 Bi1 I7 85.957(11) . 1_545 ?
I1 Bi1 I4 89.578(12) . . ?
I1 Bi1 I7 86.160(10) . 1_545 ?
I3 Bi1 I4 94.928(12) . . ?
I3 Bi1 I2 92.237(12) . . ?
I3 Bi1 I5 91.383(12) . . ?
I3 Bi1 I1 96.476(11) . . ?
I3 Bi1 I7 177.186(13) . 1_545 ?
Bi2 I8 Bi2 125.283(18) 2_556 . ?
Bi2 I4 Bi1 88.816(12) . . ?
Bi1 I2 Bi2 93.009(11) . 1_545 ?
Bi1 I5 Bi2 88.916(12) . . ?
Bi1 I1 Bi1 125.151(19) . 2_656 ?
Bi2 I7 Bi1 92.773(11) . 1_565 ?
C6 N5 C1 122.2(5) . . ?
C6 N5 C2 122.8(5) . . ?
C2 N5 C1 114.9(5) . . ?
N6 C5 C1 122.2(5) . . ?
N6 C5 C2 122.8(5) . . ?
C2 C5 C1 114.9(5) . . ?
C5 N6 C4 123.0(6) . . ?
C5 N6 C3 121.3(5) . . ?
C4 N6 C3 115.7(5) . . ?
N5 C6 C4 123.0(6) . . ?
N5 C6 C3 121.3(5) . . ?
C4 C6 C3 115.7(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
