# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_100K
_database_code_depnum_ccdc_archive 'CCDC 1548780'
_audit_update_record             
;
2017-05-09 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H16 Bi Cl5 N2'
_chemical_formula_weight         478.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   17.5405(4)
_cell_length_b                   21.7670(4)
_cell_length_c                   7.47911(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2855.54(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9605
_cell_measurement_theta_min      2.8750
_cell_measurement_theta_max      36.8544

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.226
_exptl_crystal_F_000             3552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    13.247

_diffrn_ambient_temperature      100(2)
_exptl_absorpt_correction_T_min  0.19258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            11801
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         29.570
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2869
_reflns_number_gt                2687
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0758P)²+0.7008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.462(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2869
_refine_ls_number_parameters     138
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.63291(2) 0.13657(2) 0.0000(16) 0.01782(14) Uani 1 1 d . . . . .
Cl1 Cl 0.54866(16) 0.11383(19) 0.2780(16) 0.0373(7) Uani 1 1 d . . . . .
Cl11 Cl 0.52667(15) 0.12145(14) -0.2250(16) 0.0270(5) Uani 1 1 d . . . . .
Cl2 Cl 0.59225(15) 0.25439(12) 0.0432(16) 0.0257(5) Uani 1 1 d . . . . .
Cl3 Cl 0.67084(14) 0.01592(11) -0.0283(17) 0.0421(9) Uani 1 1 d . . . . .
Cl4 Cl 0.72689(14) 0.16195(14) -0.2993(16) 0.0308(5) Uani 1 1 d . . . . .
N1A N 0.5945(5) 0.2415(4) 0.483(2) 0.0322(19) Uani 1 1 d . . . . .
H1 H 0.6024 0.2422 0.3657 0.048 Uiso 1 1 calc R U . . .
H2 H 0.5452 0.2354 0.5047 0.048 Uiso 1 1 calc R U . . .
H3 H 0.6215 0.2112 0.5319 0.048 Uiso 1 1 calc R U . . .
C1A C 0.6183(7) 0.3009(5) 0.562(2) 0.029(2) Uani 1 1 d . . . . .
H4 H 0.5785 0.3311 0.5426 0.034 Uiso 1 1 calc R U . . .
H5 H 0.6251 0.2960 0.6897 0.034 Uiso 1 1 calc R U . . .
C2A C 0.6902(6) 0.3233(5) 0.482(3) 0.037(2) Uani 1 1 d . . . . .
H6 H 0.7323 0.3004 0.5300 0.056 Uiso 1 1 calc R U . . .
H7 H 0.6966 0.3661 0.5095 0.056 Uiso 1 1 calc R U . . .
H8 H 0.6885 0.3180 0.3546 0.056 Uiso 1 1 calc R U . . .
N1B N 0.3542(12) -0.0285(7) 0.521(4) 0.028(5) Uani 0.63(3) 1 d D U P A 1
H9 H 0.3507 -0.0292 0.6401 0.041 Uiso 0.63(3) 1 calc R U P A 1
H10 H 0.3768 -0.0628 0.4836 0.041 Uiso 0.63(3) 1 calc R U P A 1
H11 H 0.3078 -0.0259 0.4741 0.041 Uiso 0.63(3) 1 calc R U P A 1
C2B C 0.3554(10) 0.0831(7) 0.486(5) 0.041(5) Uani 0.63(3) 1 d D U P A 1
H12 H 0.3176 0.0858 0.3936 0.062 Uiso 0.63(3) 1 calc R U P A 1
H13 H 0.3898 0.1172 0.4764 0.062 Uiso 0.63(3) 1 calc R U P A 1
H14 H 0.3309 0.0841 0.6008 0.062 Uiso 0.63(3) 1 calc R U P A 1
C1B C 0.3990(8) 0.0242(5) 0.467(3) 0.031(5) Uani 0.63(3) 1 d D U P A 1
H15 H 0.4142 0.0192 0.3428 0.038 Uiso 0.63(3) 1 calc R U P A 1
H16 H 0.4449 0.0263 0.5388 0.038 Uiso 0.63(3) 1 calc R U P A 1
N11B N 0.348(2) -0.0214(10) 0.566(6) 0.022(8) Uani 0.37(3) 1 d D U P A -1
H17 H 0.3006 -0.0258 0.5221 0.033 Uiso 0.37(3) 1 calc R U P A -1
H18 H 0.3482 -0.0326 0.6800 0.033 Uiso 0.37(3) 1 calc R U P A -1
H19 H 0.3797 -0.0449 0.5038 0.033 Uiso 0.37(3) 1 calc R U P A -1
C21B C 0.3565(17) 0.0722(13) 0.373(2) 0.025(7) Uani 0.37(3) 1 d D U P A -1
H20 H 0.3750 0.0460 0.2793 0.037 Uiso 0.37(3) 1 calc R U P A -1
H21 H 0.3826 0.1110 0.3684 0.037 Uiso 0.37(3) 1 calc R U P A -1
H22 H 0.3028 0.0788 0.3575 0.037 Uiso 0.37(3) 1 calc R U P A -1
C11B C 0.3706(16) 0.0424(9) 0.551(2) 0.028(9) Uani 0.37(3) 1 d D U P A -1
H23 H 0.4247 0.0450 0.5768 0.034 Uiso 0.37(3) 1 calc R U P A -1
H24 H 0.3439 0.0658 0.6416 0.034 Uiso 0.37(3) 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl11 2.532(3) . ?
Bi1 Cl1 2.598(3) . ?
Bi1 Cl2 2.682(3) . ?
Bi1 Cl3 2.717(3) . ?
Bi1 Cl4 2.834(3) . ?
Bi1 Cl4 2.934(3) 8_645 ?
Cl4 Bi1 2.934(3) 8_644 ?
N1A C1A 1.480(14) . ?
N1A H1 0.8900 . ?
N1A H2 0.8900 . ?
N1A H3 0.8900 . ?
C1A C2A 1.478(16) . ?
C1A H4 0.9700 . ?
C1A H5 0.9700 . ?
C2A H6 0.9600 . ?
C2A H7 0.9600 . ?
C2A H8 0.9600 . ?
N1B C1B 1.4501(12) . ?
N1B H9 0.8900 . ?
N1B H10 0.8900 . ?
N1B H11 0.8900 . ?
C2B C1B 1.5000(12) . ?
C2B H12 0.9600 . ?
C2B H13 0.9600 . ?
C2B H14 0.9600 . ?
C1B H15 0.9700 . ?
C1B H16 0.9700 . ?
N11B C11B 1.4501(12) . ?
N11B H17 0.8900 . ?
N11B H18 0.8900 . ?
N11B H19 0.8900 . ?
C21B C11B 1.4999(12) . ?
C21B H20 0.9600 . ?
C21B H21 0.9600 . ?
C21B H22 0.9600 . ?
C11B H23 0.9700 . ?
C11B H24 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
Cl11 Bi1 Cl1 95.08(10) . . ?
Cl11 Bi1 Cl2 90.50(9) . . ?
Cl1 Bi1 Cl2 86.24(11) . . ?
Cl11 Bi1 Cl3 90.17(10) . . ?
Cl1 Bi1 Cl3 91.00(13) . . ?
Cl2 Bi1 Cl3 177.21(12) . . ?
Cl11 Bi1 Cl4 85.90(10) . . ?
Cl1 Bi1 Cl4 179.02(10) . . ?
Cl2 Bi1 Cl4 93.64(8) . . ?
Cl3 Bi1 Cl4 89.12(11) . . ?
Cl11 Bi1 Cl4 168.92(10) . 8_645 ?
Cl1 Bi1 Cl4 95.92(10) . 8_645 ?
Cl2 Bi1 Cl4 88.92(8) . 8_645 ?
Cl3 Bi1 Cl4 90.95(9) . 8_645 ?
Cl4 Bi1 Cl4 83.10(3) . 8_645 ?
Bi1 Cl4 Bi1 148.76(11) . 8_644 ?
C1A N1A H1 109.5 . . ?
C1A N1A H2 109.5 . . ?
H1 N1A H2 109.5 . . ?
C1A N1A H3 109.5 . . ?
H1 N1A H3 109.5 . . ?
H2 N1A H3 109.5 . . ?
C2A C1A N1A 111.7(10) . . ?
C2A C1A H4 109.3 . . ?
N1A C1A H4 109.3 . . ?
C2A C1A H5 109.3 . . ?
N1A C1A H5 109.3 . . ?
H4 C1A H5 107.9 . . ?
C1A C2A H6 109.5 . . ?
C1A C2A H7 109.5 . . ?
H6 C2A H7 109.5 . . ?
C1A C2A H8 109.5 . . ?
H6 C2A H8 109.5 . . ?
H7 C2A H8 109.5 . . ?
C1B N1B H9 109.5 . . ?
C1B N1B H10 109.5 . . ?
H9 N1B H10 109.5 . . ?
C1B N1B H11 109.5 . . ?
H9 N1B H11 109.5 . . ?
H10 N1B H11 109.5 . . ?
C1B C2B H12 109.5 . . ?
C1B C2B H13 109.5 . . ?
H12 C2B H13 109.5 . . ?
C1B C2B H14 109.5 . . ?
H12 C2B H14 109.5 . . ?
H13 C2B H14 109.5 . . ?
N1B C1B C2B 111.9(15) . . ?
N1B C1B H15 109.2 . . ?
C2B C1B H15 109.2 . . ?
N1B C1B H16 109.2 . . ?
C2B C1B H16 109.2 . . ?
H15 C1B H16 107.9 . . ?
C11B N11B H17 109.5 . . ?
C11B N11B H18 109.5 . . ?
H17 N11B H18 109.5 . . ?
C11B N11B H19 109.5 . . ?
H17 N11B H19 109.5 . . ?
H18 N11B H19 109.5 . . ?
C11B C21B H20 109.5 . . ?
C11B C21B H21 109.5 . . ?
H20 C21B H21 109.5 . . ?
C11B C21B H22 109.5 . . ?
H20 C21B H22 109.5 . . ?
H21 C21B H22 109.5 . . ?
N11B C11B C21B 116(2) . . ?
N11B C11B H23 108.3 . . ?
C21B C11B H23 108.3 . . ?
N11B C11B H24 108.3 . . ?
C21B C11B H24 108.3 . . ?
H23 C11B H24 107.4 . . ?

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


N1A H1 Cl2 0.89 2.43 3.303(11) 165.7 .
N1A H2 Cl2 0.89 2.44 3.307(9) 165.7 6_655
N1A H3 Cl4 0.89 2.48 3.323(10) 157.7 1_556
N1B H9 Cl3 0.89 2.53 3.41(3) 171.1 2_656
N1B H10 Cl1 0.89 2.30 3.11(2) 150.2 2_655
N1B H11 Cl3 0.89 2.41 3.25(2) 157.0 7_445
N11B H17 Cl3 0.89 2.32 3.18(4) 163.3 7_445
N11B H18 Cl3 0.89 2.24 3.06(4) 153.0 2_656
N11B H19 Cl1 0.89 2.59 3.46(4) 168.6 2_655


_refine_diff_density_max         1.675
_refine_diff_density_min         -2.173
_refine_diff_density_rms         0.277

####################################################################### 
# 
# 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_PhaseI
_database_code_depnum_ccdc_archive 'CCDC 1548779'
_audit_update_record             
;
2017-05-09 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H16 Bi Cl5 N2'
_chemical_formula_weight         478.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        Acam
_space_group_name_Hall           ?

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'x-1/2, -y, z+1/2'
'-x-1/2, y, z+1/2'

_cell_length_a                   17.8318(2)
_cell_length_b                   21.9673(8)
_cell_length_c                   7.5656(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2963.57(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    11166
_cell_measurement_theta_min      3.0460
_cell_measurement_theta_max      29.5680

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    12.764

_diffrn_ambient_temperature      295(2)
_exptl_absorpt_correction_T_min  0.30102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            32217
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2229
_reflns_number_gt                1917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+4P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2229
_refine_ls_number_parameters     78
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.63354(2) 0.13566(2) 0.0000 0.04449(9) Uani 1 2 d S T P . .
Cl1 Cl 0.53802(9) 0.12052(7) 0.25187(19) 0.0863(4) Uani 1 1 d . . . . .
Cl2 Cl 0.59715(14) 0.25380(9) 0.0000 0.0907(6) Uani 1 2 d S T P . .
Cl3 Cl 0.66899(12) 0.01674(9) 0.0000 0.1038(8) Uani 1 2 d S T P . .
Cl4 Cl 0.7500 0.15497(15) -0.2500 0.1364(12) Uani 1 2 d S T P . .
N1B N 0.3504(4) -0.0312(3) 0.5000 0.086(2) Uani 0.5 2 d DS TU P . .
H1 H 0.3114 -0.0233 0.4303 0.129 Uiso 0.25 1 calc R U P . .
H2 H 0.3344 -0.0486 0.5993 0.129 Uiso 0.25 1 calc R U P . .
H3 H 0.3818 -0.0562 0.4446 0.129 Uiso 0.25 1 calc R U P . .
N11B N 0.3504(4) -0.0312(3) 0.5000 0.086(2) Uani 0.5 2 d S T P . .
H4 H 0.3806 -0.0551 0.5627 0.129 Uiso 0.25 1 calc R U P . .
H5 H 0.3375 -0.0500 0.4004 0.129 Uiso 0.25 1 calc R U P . .
H6 H 0.3094 -0.0230 0.5627 0.129 Uiso 0.25 1 calc R U P . .
C1B C 0.3893(7) 0.0258(4) 0.543(2) 0.102(4) Uani 0.5 1 d D U P . .
H7 H 0.4414 0.0233 0.5060 0.122 Uiso 0.5 1 calc R U P . .
H8 H 0.3880 0.0329 0.6690 0.122 Uiso 0.5 1 calc R U P . .
C2B C 0.3515(7) 0.0771(5) 0.448(2) 0.108(5) Uani 0.5 1 d D U P . .
H9 H 0.3258 0.0616 0.3461 0.162 Uiso 0.5 1 calc R U P . .
H10 H 0.3883 0.1064 0.4119 0.162 Uiso 0.5 1 calc R U P . .
H11 H 0.3160 0.0962 0.5260 0.162 Uiso 0.5 1 calc R U P . .
N1A N 0.4097(7) 0.2567(5) 0.0000 0.146(3) Uani 0.5 2 d DS TU P . .
H12 H 0.4469 0.2507 -0.0766 0.219 Uiso 0.25 1 calc R U P . .
H13 H 0.4265 0.2783 0.0913 0.219 Uiso 0.25 1 calc R U P . .
H14 H 0.3727 0.2768 -0.0529 0.219 Uiso 0.25 1 calc R U P . .
N11A N 0.4097(7) 0.2567(5) 0.0000 0.146(3) Uani 0.5 2 d S T P . .
H15 H 0.4242 0.2791 -0.0919 0.219 Uiso 0.25 1 calc R U P . .
H16 H 0.4485 0.2507 0.0720 0.219 Uiso 0.25 1 calc R U P . .
H17 H 0.3734 0.2760 0.0581 0.219 Uiso 0.25 1 calc R U P . .
C1A C 0.3830(8) 0.2004(7) 0.060(3) 0.153(4) Uani 0.5 1 d D U P . .
H18 H 0.3804 0.2027 0.1880 0.183 Uiso 0.5 1 calc R U P . .
H19 H 0.4209 0.1703 0.0317 0.183 Uiso 0.5 1 calc R U P . .
C2A C 0.3128(7) 0.1769(7) 0.0000 0.159(4) Uani 0.5 2 d DS TU P . .
H20 H 0.2869 0.2077 -0.0662 0.238 Uiso 0.25 1 calc R U P . .
H21 H 0.2829 0.1652 0.0999 0.238 Uiso 0.25 1 calc R U P . .
H22 H 0.3214 0.1421 -0.0741 0.238 Uiso 0.25 1 calc R U P . .
C21A C 0.3128(7) 0.1769(7) 0.0000 0.159(4) Uani 0.5 2 d S T P . .
H23 H 0.2738 0.2058 -0.0252 0.238 Uiso 0.25 1 calc R U P . .
H24 H 0.3151 0.1699 0.1251 0.238 Uiso 0.25 1 calc R U P . .
H25 H 0.3022 0.1393 -0.0596 0.238 Uiso 0.25 1 calc R U P . .


_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 Cl1 2.5774(12) . ?
Bi1 Cl1 2.5774(12) 10 ?
Bi1 Cl2 2.6752(19) . ?
Bi1 Cl3 2.6878(19) . ?
Bi1 Cl4 2.8408(5) 10 ?
Bi1 Cl4 2.8408(5) . ?
Cl4 Bi1 2.8408(5) 7_644 ?
N1B C1B 1.468(8) . ?
N1B H1 0.8900 . ?
N1B H2 0.8900 . ?
N1B H3 0.8900 . ?
C1B C2B 1.494(9) . ?
C1B H7 0.9700 . ?
C1B H8 0.9700 . ?
C2B H9 0.9600 . ?
C2B H10 0.9600 . ?
C2B H11 0.9600 . ?
N1A C1A 1.401(9) . ?
N1A H12 0.8900 . ?
N1A H13 0.8900 . ?
N1A H14 0.8900 . ?
C1A C2A 1.428(9) . ?
C1A H18 0.9700 . ?
C1A H19 0.9700 . ?
C2A H20 0.9600 . ?
C2A H21 0.9600 . ?
C2A H22 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
Cl1 Bi1 Cl1 95.35(8) . 10 ?
Cl1 Bi1 Cl2 87.99(5) . . ?
Cl1 Bi1 Cl2 87.99(5) 10 . ?
Cl1 Bi1 Cl3 91.72(5) . . ?
Cl1 Bi1 Cl3 91.72(5) 10 . ?
Cl2 Bi1 Cl3 179.57(7) . . ?
Cl1 Bi1 Cl4 90.58(4) . 10 ?
Cl1 Bi1 Cl4 174.06(4) 10 10 ?
Cl2 Bi1 Cl4 91.86(8) . 10 ?
Cl3 Bi1 Cl4 88.46(7) . 10 ?
Cl1 Bi1 Cl4 174.06(4) . . ?
Cl1 Bi1 Cl4 90.58(4) 10 . ?
Cl2 Bi1 Cl4 91.86(8) . . ?
Cl3 Bi1 Cl4 88.46(7) . . ?
Cl4 Bi1 Cl4 83.487(19) 10 . ?
Bi1 Cl4 Bi1 162.82(13) . 7_644 ?
C1B N1B H1 109.5 . . ?
C1B N1B H2 109.5 . . ?
H1 N1B H2 109.5 . . ?
C1B N1B H3 109.5 . . ?
H1 N1B H3 109.5 . . ?
H2 N1B H3 109.5 . . ?
N1B C1B C2B 109.0(9) . . ?
N1B C1B H7 109.9 . . ?
C2B C1B H7 109.9 . . ?
N1B C1B H8 109.9 . . ?
C2B C1B H8 109.9 . . ?
H7 C1B H8 108.3 . . ?
C1B C2B H9 109.5 . . ?
C1B C2B H10 109.5 . . ?
H9 C2B H10 109.5 . . ?
C1B C2B H11 109.5 . . ?
H9 C2B H11 109.5 . . ?
H10 C2B H11 109.5 . . ?
C1A N1A H12 109.5 . . ?
C1A N1A H13 109.5 . . ?
H12 N1A H13 109.5 . . ?
C1A N1A H14 109.5 . . ?
H12 N1A H14 109.5 . . ?
H13 N1A H14 109.5 . . ?
N1A C1A C2A 120.9(14) . . ?
N1A C1A H18 107.1 . . ?
C2A C1A H18 107.1 . . ?
N1A C1A H19 107.1 . . ?
C2A C1A H19 107.1 . . ?
H18 C1A H19 106.8 . . ?
C1A C2A H20 109.5 . . ?
C1A C2A H21 109.5 . . ?
H20 C2A H21 109.5 . . ?
C1A C2A H22 109.5 . . ?
H20 C2A H22 109.5 . . ?
H21 C2A H22 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




N1B H6 Cl3 0.89 2.55 3.250(7) 135.9 15
N1B H3 Cl1 0.89 2.48 3.367(6) 172.1 2_655
N1A H16 Cl2 0.89 2.71 3.343(12) 129.4 .
N1A H13 Cl1 0.89 2.60 3.416(8) 153.2 13_655



_refine_diff_density_max         0.859
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.130

