# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1432420'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-01-22 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_structural     (C5H5NCH3)[BiBr4]
_chemical_formula_sum            'C6 H8 Bi Br4 N'
_chemical_formula_weight         622.75

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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.47341(15)
_cell_length_b                   13.3443(2)
_cell_length_c                   12.4703(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.9932(16)
_cell_angle_gamma                90.00
_cell_volume                     1242.87(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3413
_cell_measurement_theta_min      4.1770
_cell_measurement_theta_max      30.6140
_cell_oxdiff_length_a            7.47513(16)
_cell_oxdiff_length_b            13.3411(3)
_cell_oxdiff_length_c            12.4701(2)
_cell_oxdiff_angle_alpha         89.9861(16)
_cell_oxdiff_angle_beta          91.9586(15)
_cell_oxdiff_angle_gamma         89.9721(18)
_cell_oxdiff_volume              1242.87(4)
_cell_oxdiff_measurement_reflns_used 3413

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    27.000
_exptl_absorpt_correction_T_min  0.52109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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.
;

_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_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  'New Xcalibur, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            6811
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.4636
_diffrn_reflns_theta_max         31.0475
_diffrn_measured_fraction_theta_max 0.8634
_diffrn_reflns_theta_full        28.2205
_diffrn_measured_fraction_theta_full 0.9960
_diffrn_orient_matrix_UB_11      -0.0853165000
_diffrn_orient_matrix_UB_12      -0.0138909000
_diffrn_orient_matrix_UB_13      -0.0217752000
_diffrn_orient_matrix_UB_21      0.0323681000
_diffrn_orient_matrix_UB_22      -0.0490140000
_diffrn_orient_matrix_UB_23      -0.0098424000
_diffrn_orient_matrix_UB_31      -0.0262231000
_diffrn_orient_matrix_UB_32      -0.0152105000
_diffrn_orient_matrix_UB_33      0.0516535000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00    5.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.8209  -99.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   58.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.8209   57.0000  150.0000 138

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   92.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2897   38.0000  -60.0000 202

;
_reflns_number_total             3431
_reflns_number_gt                3003
_reflns_threshold_expression     >2σ(I)
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_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_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelxLe (Sheldrick, 2011)'
_computing_publication_material  'CIFTAB-2014/7 (Sheldrick, 2014)'
_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)+(0.0129P)²] 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         3431
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0440
_refine_ls_wR_factor_gt          0.0424
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_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
C5 C 1.3430(6) 0.4711(4) 0.6141(3) 0.0293(11) Uani 1 1 d . . . . .
H5A H 1.3892 0.4991 0.6794 0.035 Uiso 1 1 calc R U . . .
C6 C 1.2718(6) 0.5331(4) 0.5342(4) 0.0276(10) Uani 1 1 d . . . . .
H6A H 1.2712 0.6038 0.5432 0.033 Uiso 1 1 calc R U . . .
C7 C 1.2018(6) 0.4899(3) 0.4415(3) 0.0220(9) Uani 1 1 d . . . . .
H7A H 1.1518 0.5312 0.3860 0.026 Uiso 1 1 calc R U . . .
C8 C 1.1214(6) 0.3451(3) 0.3304(3) 0.0237(9) Uani 1 1 d . . . . .
H8A H 1.1341 0.2720 0.3338 0.036 Uiso 1 1 calc R U . . .
H8B H 0.9941 0.3627 0.3249 0.036 Uiso 1 1 calc R U . . .
H8C H 1.1817 0.3706 0.2674 0.036 Uiso 1 1 calc R U . . .
C9 C 1.3468(6) 0.3697(4) 0.5987(3) 0.0288(11) Uani 1 1 d . . . . .
H9A H 1.3982 0.3269 0.6524 0.035 Uiso 1 1 calc R U . . .
C11 C 1.2757(5) 0.3303(3) 0.5051(3) 0.0201(9) Uani 1 1 d . . . . .
H11A H 1.2774 0.2599 0.4940 0.024 Uiso 1 1 calc R U . . .
Br1 Br 0.44464(5) 0.08954(3) 0.62427(3) 0.01669(8) Uani 1 1 d . . . . .
N1 N 1.2038(4) 0.3905(2) 0.4290(2) 0.0149(7) Uani 1 1 d . . . . .
Br2 Br 1.05400(5) 0.06413(3) 0.35641(3) 0.01815(9) Uani 1 1 d . . . . .
Br3 Br 0.59873(5) 0.21390(3) 0.34615(3) 0.01906(9) Uani 1 1 d . . . . .
Br4 Br 0.89846(5) 0.23959(3) 0.60176(3) 0.01981(9) Uani 1 1 d . . . . .
Bi1 Bi 0.75002(2) 0.08766(2) 0.48962(2) 0.01258(4) Uani 1 1 d . . . . .


_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
C5 C9 1.368(6) . ?
C5 C6 1.387(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.379(6) . ?
C6 H6A 0.9500 . ?
C7 N1 1.336(5) . ?
C7 H7A 0.9500 . ?
C8 N1 1.485(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.371(6) . ?
C9 H9A 0.9500 . ?
C11 N1 1.341(5) . ?
C11 H11A 0.9500 . ?
Br1 Bi1 2.8802(4) . ?
Br1 Bi1 3.0953(4) 3_656 ?
Br2 Bi1 2.8777(4) . ?
Br2 Bi1 3.1207(4) 3_756 ?
Br3 Bi1 2.6788(4) . ?
Br4 Bi1 2.6812(4) . ?
Bi1 Br1 3.0953(4) 3_656 ?
Bi1 Br2 3.1207(4) 3_756 ?

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
C9 C5 C6 120.0(4) . . ?
C9 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C5 118.5(4) . . ?
C7 C6 H6A 120.7 . . ?
C5 C6 H6A 120.7 . . ?
N1 C7 C6 120.5(4) . . ?
N1 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 C11 119.3(4) . . ?
C5 C9 H9A 120.4 . . ?
C11 C9 H9A 120.4 . . ?
N1 C11 C9 120.5(4) . . ?
N1 C11 H11A 119.7 . . ?
C9 C11 H11A 119.7 . . ?
Bi1 Br1 Bi1 95.460(11) . 3_656 ?
C7 N1 C11 121.2(4) . . ?
C7 N1 C8 119.7(4) . . ?
C11 N1 C8 119.1(3) . . ?
Bi1 Br2 Bi1 94.515(11) . 3_756 ?
Br3 Bi1 Br4 91.730(13) . . ?
Br3 Bi1 Br2 90.370(12) . . ?
Br4 Bi1 Br2 93.611(13) . . ?
Br3 Bi1 Br1 93.398(12) . . ?
Br4 Bi1 Br1 90.640(12) . . ?
Br2 Bi1 Br1 174.233(13) . . ?
Br3 Bi1 Br1 89.614(12) . 3_656 ?
Br4 Bi1 Br1 175.065(11) . 3_656 ?
Br2 Bi1 Br1 91.127(11) . 3_656 ?
Br1 Bi1 Br1 84.540(11) . 3_656 ?
Br3 Bi1 Br2 175.720(12) . 3_756 ?
Br4 Bi1 Br2 89.602(12) . 3_756 ?
Br2 Bi1 Br2 85.486(11) . 3_756 ?
Br1 Bi1 Br2 90.653(11) . 3_756 ?
Br1 Bi1 Br2 89.397(11) 3_656 3_756 ?

_refine_diff_density_max         0.893
_refine_diff_density_min         -1.311
_refine_diff_density_rms         0.200

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
####################################################################### 
# 
# 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_1_b
_database_code_depnum_ccdc_archive 'CCDC 1432421'
_audit_update_record             
;
2016-01-19 deposited with the CCDC.
2016-01-22 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_structural     (C5H5NCH3)3Bi2Br9*Br2
_chemical_formula_sum            'C18 H24 Bi2 Br11 N3'
_chemical_formula_weight         1579.37

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P c a m'
_space_group_name_Hall           '-P 2c 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+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y, z'

_cell_length_a                   15.0999(3)
_cell_length_b                   10.6848(2)
_cell_length_c                   22.7470(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3669.99(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7867
_cell_measurement_theta_min      3.5590
_cell_measurement_theta_max      29.1610
_cell_oxdiff_length_a            10.6882(3)
_cell_oxdiff_length_b            15.1006(4)
_cell_oxdiff_length_c            22.7387(6)
_cell_oxdiff_angle_alpha         90.014(2)
_cell_oxdiff_angle_beta          89.986(2)
_cell_oxdiff_angle_gamma         90.040(2)
_cell_oxdiff_volume              3669.99(17)
_cell_oxdiff_measurement_reflns_used 7867

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.858
_exptl_crystal_F_000             2816
_exptl_transmission_factor_min   0.63123
_exptl_transmission_factor_max   1.00000
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    21.567
_exptl_absorpt_correction_T_min  0.63123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      296.00(10)
_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  'New Xcalibur, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            19785
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_av_R_equivalents  0.1063
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.2946
_diffrn_reflns_theta_max         25.6794
_diffrn_measured_fraction_theta_max 0.9957
_diffrn_reflns_theta_full        25.6263
_diffrn_measured_fraction_theta_full 0.9957
_diffrn_orient_matrix_UB_11      -0.0272209000
_diffrn_orient_matrix_UB_12      0.0064033000
_diffrn_orient_matrix_UB_13      -0.0281235000
_diffrn_orient_matrix_UB_21      0.0500490000
_diffrn_orient_matrix_UB_22      -0.0237025000
_diffrn_orient_matrix_UB_23      -0.0130981000
_diffrn_orient_matrix_UB_31      -0.0340320000
_diffrn_orient_matrix_UB_32      -0.0400439000
_diffrn_orient_matrix_UB_33      0.0032469000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   16.00   0.5000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.8209   57.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   67.00   0.5000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2897   38.0000 -180.0000 142

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00   63.00   0.5000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       16.2897  -19.0000  -30.0000 256

;
_reflns_number_total             6032
_reflns_number_gt                4661
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelxLe (Sheldrick, 2011)'
_computing_publication_material  'CIFTAB-2014/7 (Sheldrick, 2014)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+13.5676P] 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         3566
_refine_ls_number_parameters     174
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_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
N1 N 0.0924(6) 0.8398(9) 0.5924(4) 0.060(3) Uani 1 1 d D . . . .
C1 C 0.0700(12) 0.7681(15) 0.5468(6) 0.096(5) Uani 1 1 d D . . . .
H1 H 0.0893 0.7884 0.5092 0.115 Uiso 1 1 calc R U . . .
C2 C 0.0197(12) 0.6671(15) 0.5554(7) 0.110(6) Uani 1 1 d D . . . .
H2 H 0.0020 0.6191 0.5234 0.132 Uiso 1 1 calc R U . . .
C3 C -0.0056(11) 0.6342(14) 0.6096(6) 0.100(5) Uani 1 1 d D . . . .
H3 H -0.0384 0.5616 0.6155 0.120 Uiso 1 1 calc R U . . .
C4 C 0.0168(10) 0.7065(12) 0.6550(6) 0.084(5) Uani 1 1 d D . . . .
H4 H -0.0013 0.6851 0.6928 0.101 Uiso 1 1 calc R U . . .
C5 C 0.0650(9) 0.8093(12) 0.6464(6) 0.071(3) Uani 1 1 d D . . . .
H5 H 0.0796 0.8601 0.6782 0.085 Uiso 1 1 calc R U . . .
C6 C 0.1425(10) 0.9559(14) 0.5827(8) 0.105(5) Uani 1 1 d D . . . .
H6A H 0.1072 1.0134 0.5603 0.157 Uiso 1 1 calc R U . . .
H6B H 0.1960 0.9373 0.5616 0.157 Uiso 1 1 calc R U . . .
H6C H 0.1571 0.9928 0.6199 0.157 Uiso 1 1 calc R U . . .
N2 N 0.2202(12) 1.3921(16) 0.7500 0.107(3) Uani 1 2 d DS TU P . .
C7 C 0.2435(10) 1.3383(13) 0.6992(7) 0.107(3) Uani 1 1 d D U . . .
H7 H 0.2301 1.3770 0.6637 0.129 Uiso 1 1 calc R U . . .
C8 C 0.2859(10) 1.2291(13) 0.6997(8) 0.108(3) Uani 1 1 d D U . . .
H8 H 0.2988 1.1895 0.6643 0.129 Uiso 1 1 calc R U . . .
C9 C 0.3102(15) 1.176(2) 0.7500 0.108(3) Uani 1 2 d DS TU P . .
H9 H 0.3434 1.1025 0.7500 0.129 Uiso 1 2 calc R U P . .
C10 C 0.1716(14) 1.5115(18) 0.7500 0.107(3) Uani 1 2 d DS TU P . .
H10A H 0.2052 1.5733 0.7290 0.161 Uiso 0.5 1 calc R U P A -1
H10B H 0.1627 1.5388 0.7898 0.161 Uiso 0.5 1 calc R U P A -1
H10C H 0.1152 1.5002 0.7312 0.161 Uiso 0.5 1 calc R U P A -1
Bi1 Bi 0.40770(2) 0.77668(4) 0.66241(2) 0.03912(16) Uani 1 1 d . . . . .
Br1 Br 0.55244(8) 0.69984(13) 0.60349(6) 0.0681(4) Uani 1 1 d . . . . .
Br2 Br 0.39083(8) 0.98639(11) 0.59352(5) 0.0564(3) Uani 1 1 d . . . . .
Br3 Br 0.29535(8) 0.64175(12) 0.59305(6) 0.0702(4) Uani 1 1 d . . . . .
Br4 Br 0.25953(9) 0.84760(14) 0.7500 0.0508(4) Uani 1 2 d S T P . .
Br5 Br 0.42485(10) 0.56348(13) 0.7500 0.0498(4) Uani 1 2 d S T P . .
Br6 Br 0.52254(11) 0.91564(17) 0.7500 0.0619(5) Uani 1 2 d S T P . .
Br11 Br 0.2847(2) 0.2141(2) 0.52586(13) 0.0761(8) Uani 0.5 1 d . . P B -1
Br12 Br 0.23705(17) 0.3926(2) 0.47752(10) 0.0671(6) Uani 0.5 1 d . . P B -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
N1 C1 1.332(12) . ?
N1 C5 1.337(11) . ?
N1 C6 1.470(15) . ?
C1 C2 1.334(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.337(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.334(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.331(9) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N2 C7 1.338(12) . ?
N2 C7 1.338(12) 6_557 ?
N2 C10 1.471(16) . ?
C7 C8 1.331(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.330(9) . ?
C8 H8 0.9300 . ?
C9 C8 1.330(9) 6_557 ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Bi1 Br1 2.6922(12) . ?
Bi1 Br3 2.7286(11) . ?
Bi1 Br2 2.7461(11) . ?
Bi1 Br6 3.0301(12) . ?
Bi1 Br5 3.0374(11) . ?
Bi1 Br4 3.0902(11) . ?
Br4 Bi1 3.0902(11) 6_557 ?
Br5 Bi1 3.0374(11) 6_557 ?
Br6 Bi1 3.0300(12) 6_557 ?
Br11 Br12 2.317(4) . ?

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
C1 N1 C5 119.8(12) . . ?
C1 N1 C6 120.0(12) . . ?
C5 N1 C6 120.2(12) . . ?
N1 C1 C2 119.7(13) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 120.7(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.3(13) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.2(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 N1 120.3(12) . . ?
C4 C5 H5 119.9 . . ?
N1 C5 H5 119.9 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 N2 C7 119(2) . 6_557 ?
C7 N2 C10 120.2(10) . . ?
C7 N2 C10 120.2(10) 6_557 . ?
C8 C7 N2 119.7(17) . . ?
C8 C7 H7 120.1 . . ?
N2 C7 H7 120.1 . . ?
C9 C8 C7 121(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C8 119(3) 6_557 . ?
C8 C9 H9 120.6 6_557 . ?
C8 C9 H9 120.6 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br1 Bi1 Br3 93.19(4) . . ?
Br1 Bi1 Br2 92.29(4) . . ?
Br3 Bi1 Br2 92.50(4) . . ?
Br1 Bi1 Br6 90.70(4) . . ?
Br3 Bi1 Br6 174.21(4) . . ?
Br2 Bi1 Br6 91.63(4) . . ?
Br1 Bi1 Br5 91.64(4) . . ?
Br3 Bi1 Br5 92.06(4) . . ?
Br2 Bi1 Br5 173.80(3) . . ?
Br6 Bi1 Br5 83.53(4) . . ?
Br1 Bi1 Br4 169.60(4) . . ?
Br3 Bi1 Br4 92.99(4) . . ?
Br2 Bi1 Br4 95.78(4) . . ?
Br6 Bi1 Br4 82.55(4) . . ?
Br5 Bi1 Br4 79.79(3) . . ?
Bi1 Br4 Bi1 80.29(4) 6_557 . ?
Bi1 Br5 Bi1 81.98(4) 6_557 . ?
Bi1 Br6 Bi1 82.22(4) 6_557 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1(2) . . . . ?
C6 N1 C1 C2 -175.7(16) . . . . ?
N1 C1 C2 C3 -3(3) . . . . ?
C1 C2 C3 C4 3(3) . . . . ?
C2 C3 C4 C5 -1(3) . . . . ?
C3 C4 C5 N1 -1(2) . . . . ?
C1 N1 C5 C4 1(2) . . . . ?
C6 N1 C5 C4 177.6(14) . . . . ?
C7 N2 C7 C8 3(3) 6_557 . . . ?
C10 N2 C7 C8 -178.7(17) . . . . ?
N2 C7 C8 C9 -4(3) . . . . ?
C7 C8 C9 C8 5(4) . . . 6_557 ?

_refine_diff_density_max         1.722
_refine_diff_density_min         -1.926
_refine_diff_density_rms         0.256

