# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1445036'
_audit_update_record             
;
2016-01-03 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 Bi Br2 N S2'
_chemical_formula_sum            'C5 H10 Bi Br2 N S2'
_chemical_formula_weight         517.06

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   10.0768(6)
_cell_length_b                   14.7660(9)
_cell_length_c                   7.8460(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.716(5)
_cell_angle_gamma                90.00
_cell_volume                     1166.91(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.30(10)
_cell_measurement_reflns_used    2158
_cell_measurement_theta_min      3.5010
_cell_measurement_theta_max      28.7570

_exptl_crystal_description       rectangles
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.943
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    22.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.21743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4395
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2049
_reflns_number_gt                1692
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0714P)²+3.4155P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2049
_refine_ls_number_parameters     100
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.141
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.8724(3) 0.3862(2) 1.0026(4) 0.0117(7) Uani 1 1 d . . .
S2 S 0.6669(3) 0.4495(2) 0.7523(4) 0.0148(8) Uani 1 1 d . . .
Br1 Br 0.95803(12) 0.34375(10) 0.48564(17) 0.0146(4) Uani 1 1 d . . .
Br2 Br 0.57588(12) 0.20968(9) 0.94573(18) 0.0133(3) Uani 1 1 d . . .
Bi1 Bi 0.77821(4) 0.29068(3) 0.73611(6) 0.0101(2) Uani 1 1 d . . .
N1 N 0.7450(10) 0.5424(8) 1.0252(14) 0.013(3) Uani 1 1 d U . .
C1 C 0.7597(11) 0.4686(9) 0.9420(17) 0.008(3) Uani 1 1 d U . .
C2 C 0.6557(13) 0.6189(9) 0.9584(18) 0.014(3) Uani 1 1 d . . .
H2A H 0.5822 0.5932 0.8919 0.017 Uiso 1 1 calc R . .
H2B H 0.6193 0.6510 1.0542 0.017 Uiso 1 1 calc R . .
C4 C 0.8164(13) 0.5613(10) 1.1922(17) 0.015(3) Uani 1 1 d U . .
H4A H 0.8436 0.6242 1.1968 0.018 Uiso 1 1 calc R . .
H4B H 0.8952 0.5238 1.2028 0.018 Uiso 1 1 calc R . .
C3 C 0.7300(15) 0.6852(11) 0.849(2) 0.026(4) Uani 1 1 d . . .
H3A H 0.6707 0.7324 0.8104 0.039 Uiso 1 1 calc R . .
H3B H 0.7639 0.6541 0.7518 0.039 Uiso 1 1 calc R . .
H3C H 0.8024 0.7112 0.9143 0.039 Uiso 1 1 calc R . .
C5 C 0.7241(12) 0.5409(10) 1.3381(18) 0.014(3) Uani 1 1 d U . .
H5A H 0.7695 0.5528 1.4450 0.021 Uiso 1 1 calc R . .
H5B H 0.6980 0.4784 1.3334 0.021 Uiso 1 1 calc R . .
H5C H 0.6466 0.5786 1.3276 0.021 Uiso 1 1 calc R . .

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
S1 0.0144(16) 0.0081(17) 0.0125(18) 0.0019(17) -0.0011(13) 0.0006(13)
S2 0.0189(17) 0.0127(18) 0.0127(18) 0.0009(17) -0.0041(13) 0.0032(14)
Br1 0.0139(6) 0.0155(8) 0.0145(7) 0.0003(7) 0.0016(5) -0.0043(6)
Br2 0.0120(6) 0.0139(8) 0.0141(8) 0.0036(7) -0.0003(5) 0.0017(5)
Bi1 0.0131(3) 0.0073(3) 0.0100(3) -0.0010(2) 0.0008(2) -0.00005(19)
N1 0.011(4) 0.016(4) 0.012(4) -0.001(4) 0.002(3) -0.002(3)
C1 0.008(4) 0.008(5) 0.007(4) -0.002(4) 0.001(3) -0.004(4)
C2 0.018(7) 0.005(7) 0.020(8) -0.005(7) 0.002(6) -0.001(6)
C4 0.014(4) 0.016(5) 0.015(5) 0.000(4) -0.002(4) 0.000(4)
C3 0.023(8) 0.014(8) 0.041(11) 0.003(9) -0.004(7) -0.002(7)
C5 0.014(4) 0.013(5) 0.016(5) 0.004(4) 0.001(4) -0.003(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
S1 C1 1.722(13) . ?
S1 Bi1 2.672(3) . ?
S2 C1 1.756(13) . ?
S2 Bi1 2.604(4) . ?
Br1 Bi1 2.8237(14) . ?
Br2 Bi1 2.9142(14) . ?
Br2 Bi1 3.0116(15) 4_566 ?
Bi1 Br2 3.0116(15) 4_565 ?
N1 C1 1.281(17) . ?
N1 C4 1.501(16) . ?
N1 C2 1.527(17) . ?
C2 C3 1.52(2) . ?
C4 C5 1.527(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 Bi1 86.6(4) . . ?
C1 S2 Bi1 88.1(4) . . ?
Bi1 Br2 Bi1 87.62(4) . 4_566 ?
S2 Bi1 S1 68.29(10) . . ?
S2 Bi1 Br1 94.02(9) . . ?
S1 Bi1 Br1 100.25(7) . . ?
S2 Bi1 Br2 91.87(8) . . ?
S1 Bi1 Br2 90.74(8) . . ?
Br1 Bi1 Br2 168.83(4) . . ?
S2 Bi1 Br2 75.86(8) . 4_565 ?
S1 Bi1 Br2 144.03(8) . 4_565 ?
Br1 Bi1 Br2 84.72(4) . 4_565 ?
Br2 Bi1 Br2 87.54(4) . 4_565 ?
C1 N1 C4 122.9(12) . . ?
C1 N1 C2 122.0(11) . . ?
C4 N1 C2 115.1(11) . . ?
N1 C1 S1 123.0(10) . . ?
N1 C1 S2 120.1(10) . . ?
S1 C1 S2 116.8(8) . . ?
C3 C2 N1 112.2(11) . . ?
N1 C4 C5 109.3(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.045
_refine_diff_density_min         -2.769
_refine_diff_density_rms         0.486
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1445037'
_audit_update_record             
;
2016-01-03 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 Bi Br N2 S4'
_chemical_formula_sum            'C6 H12 Bi Br N2 S4'
_chemical_formula_weight         529.31

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   10.2180(6)
_cell_length_b                   16.3552(9)
_cell_length_c                   8.2644(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.927(6)
_cell_angle_gamma                90.00
_cell_volume                     1356.08(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.05(10)
_cell_measurement_reflns_used    2764
_cell_measurement_theta_min      3.1840
_cell_measurement_theta_max      28.7740

_exptl_crystal_description       rods
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    16.531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.21680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4714
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2377
_reflns_number_gt                2079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0829P)²+2.5599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2377
_refine_ls_number_parameters     127
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.165
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.24662(5) 0.21057(3) 0.67573(5) 0.0097(2) Uani 1 1 d . . .
Br1 Br 0.03426(12) 0.24061(8) 0.38518(15) 0.0126(3) Uani 1 1 d . . .
S1 S 0.5321(3) 0.2321(2) 0.6909(4) 0.0167(7) Uani 1 1 d . . .
S2 S 0.3516(3) 0.13138(19) 0.4494(4) 0.0111(7) Uani 1 1 d . . .
S3 S 0.3403(3) 0.11292(19) 0.9355(4) 0.0154(7) Uani 1 1 d . . .
S4 S 0.1025(3) 0.07263(19) 0.6772(4) 0.0142(7) Uani 1 1 d . . .
C3 C 0.5920(17) 0.0724(9) 0.3389(17) 0.029(4) Uani 1 1 d . . .
H3A H 0.6770 0.0570 0.3149 0.043 Uiso 1 1 calc R . .
H3B H 0.5387 0.0969 0.2431 0.043 Uiso 1 1 calc R . .
H3C H 0.5475 0.0248 0.3695 0.043 Uiso 1 1 calc R . .
C4 C 0.2057(14) 0.0486(8) 0.8611(16) 0.016(3) Uani 1 1 d . . .
N1 N 0.6117(12) 0.1310(7) 0.4748(14) 0.018(3) Uani 1 1 d U . .
C2 C 0.7541(14) 0.1585(10) 0.5329(18) 0.027(4) Uani 1 1 d . . .
H2A H 0.8117 0.1282 0.4756 0.040 Uiso 1 1 calc R . .
H2B H 0.7797 0.1489 0.6492 0.040 Uiso 1 1 calc R . .
H2C H 0.7614 0.2157 0.5108 0.040 Uiso 1 1 calc R . .
C1 C 0.5110(13) 0.1640(7) 0.5356(15) 0.011(3) Uani 1 1 d U . .
N2 N 0.1830(12) -0.0180(7) 0.9414(14) 0.020(3) Uani 1 1 d U . .
C5 C 0.0784(16) -0.0757(9) 0.8826(18) 0.027(3) Uani 1 1 d U . .
H5A H 0.0808 -0.1191 0.9615 0.040 Uiso 1 1 calc R . .
H5B H 0.0911 -0.0981 0.7793 0.040 Uiso 1 1 calc R . .
H5C H -0.0063 -0.0486 0.8678 0.040 Uiso 1 1 calc R . .
C6 C 0.266(2) -0.0416(10) 1.0997(19) 0.047(5) Uani 1 1 d . . .
H6A H 0.2316 -0.0912 1.1380 0.071 Uiso 1 1 calc R . .
H6B H 0.2636 0.0010 1.1789 0.071 Uiso 1 1 calc R . .
H6C H 0.3558 -0.0501 1.0856 0.071 Uiso 1 1 calc R . .

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 0.0122(3) 0.0090(3) 0.0081(3) -0.00023(16) 0.0027(2) 0.00089(18)
Br1 0.0103(7) 0.0157(7) 0.0114(7) 0.0026(5) 0.0012(5) -0.0010(6)
S1 0.0128(18) 0.0187(16) 0.0189(19) -0.0053(14) 0.0039(14) -0.0028(15)
S2 0.0100(16) 0.0125(15) 0.0116(15) -0.0041(12) 0.0042(13) 0.0044(14)
S3 0.0141(17) 0.0127(16) 0.0172(16) 0.0034(13) -0.0026(13) -0.0002(14)
S4 0.0156(18) 0.0126(15) 0.0137(16) -0.0026(13) 0.0012(14) -0.0020(14)
C3 0.042(10) 0.029(8) 0.019(7) -0.006(6) 0.015(7) 0.004(8)
C4 0.020(8) 0.013(6) 0.016(7) 0.001(5) 0.005(6) -0.003(6)
N1 0.015(4) 0.020(4) 0.021(4) 0.000(3) 0.005(4) 0.002(4)
C2 0.008(7) 0.042(9) 0.027(8) 0.005(7) -0.002(6) -0.010(7)
C1 0.011(4) 0.009(4) 0.013(4) 0.001(4) 0.001(4) -0.003(4)
N2 0.025(5) 0.019(4) 0.018(4) 0.000(4) 0.007(4) -0.001(4)
C5 0.028(5) 0.023(5) 0.030(5) -0.002(4) 0.008(4) -0.009(4)
C6 0.083(16) 0.032(9) 0.019(9) 0.010(7) -0.009(9) -0.004(10)

_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 S2 2.662(3) . ?
Bi1 S4 2.696(3) . ?
Bi1 S3 2.701(3) . ?
Bi1 S1 2.917(4) . ?
Bi1 Br1 2.9564(13) . ?
Bi1 Br1 3.1251(13) 4_566 ?
Br1 Bi1 3.1251(13) 4_565 ?
S1 C1 1.682(13) . ?
S2 C1 1.735(13) . ?
S3 C4 1.748(14) . ?
S4 C4 1.723(13) . ?
C3 N1 1.461(17) . ?
C4 N2 1.319(17) . ?
N1 C1 1.341(17) . ?
N1 C2 1.512(17) . ?
N2 C5 1.440(18) . ?
N2 C6 1.468(19) . ?

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
S2 Bi1 S4 83.64(10) . . ?
S2 Bi1 S3 98.14(10) . . ?
S4 Bi1 S3 67.23(10) . . ?
S2 Bi1 S1 63.66(10) . . ?
S4 Bi1 S1 130.07(10) . . ?
S3 Bi1 S1 80.59(10) . . ?
S2 Bi1 Br1 80.88(7) . . ?
S4 Bi1 Br1 79.93(7) . . ?
S3 Bi1 Br1 147.00(8) . . ?
S1 Bi1 Br1 126.07(8) . . ?
S2 Bi1 Br1 158.12(8) . 4_566 ?
S4 Bi1 Br1 76.93(7) . 4_566 ?
S3 Bi1 Br1 83.65(8) . 4_566 ?
S1 Bi1 Br1 137.64(7) . 4_566 ?
Br1 Bi1 Br1 85.85(3) . 4_566 ?
Bi1 Br1 Bi1 90.72(4) . 4_565 ?
C1 S1 Bi1 84.6(5) . . ?
C1 S2 Bi1 91.9(4) . . ?
C4 S3 Bi1 86.5(4) . . ?
C4 S4 Bi1 87.2(4) . . ?
N2 C4 S4 119.8(10) . . ?
N2 C4 S3 121.4(10) . . ?
S4 C4 S3 118.8(7) . . ?
C1 N1 C3 123.3(12) . . ?
C1 N1 C2 121.5(11) . . ?
C3 N1 C2 115.0(12) . . ?
N1 C1 S1 123.8(10) . . ?
N1 C1 S2 116.7(9) . . ?
S1 C1 S2 119.5(8) . . ?
C4 N2 C5 124.1(12) . . ?
C4 N2 C6 122.7(13) . . ?
C5 N2 C6 113.2(12) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.783
_refine_diff_density_min         -2.406
_refine_diff_density_rms         0.576
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1445038'
_audit_update_record             
;
2016-01-03 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H40 Bi2 I2 N4 S8'
_chemical_formula_sum            'C20 H40 Bi2 I2 N4 S8'
_chemical_formula_weight         1264.80

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'
S S 0.1246 0.1234 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4033(3)
_cell_length_b                   11.2321(4)
_cell_length_c                   17.6307(6)
_cell_angle_alpha                93.566(3)
_cell_angle_beta                 98.144(3)
_cell_angle_gamma                96.906(3)
_cell_volume                     1824.02(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.05(10)
_cell_measurement_reflns_used    7599
_cell_measurement_theta_min      4.1230
_cell_measurement_theta_max      28.6730

_exptl_crystal_description       rectangles
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    11.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12422
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6419
_reflns_number_gt                5902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0496P)²+2.0118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6419
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.09865(3) 0.18775(2) 0.544329(14) 0.01282(10) Uani 1 1 d . . .
Bi2 Bi 0.12594(3) 0.68052(2) 0.041387(14) 0.01254(10) Uani 1 1 d . . .
I1 I 0.19495(5) -0.07458(4) 0.58290(3) 0.01713(13) Uani 1 1 d . . .
I2 I -0.18886(5) 0.60316(4) -0.06256(3) 0.01939(13) Uani 1 1 d . . .
S7 S 0.31222(19) 0.76692(16) 0.16660(10) 0.0145(4) Uani 1 1 d . . .
S2 S 0.1340(2) 0.36859(16) 0.45497(10) 0.0163(4) Uani 1 1 d . . .
S1 S 0.3210(2) 0.17248(16) 0.46530(10) 0.0158(4) Uani 1 1 d . . .
S6 S 0.1602(2) 0.87874(16) -0.03100(10) 0.0176(4) Uani 1 1 d . . .
S5 S 0.3686(2) 0.69788(17) -0.03226(10) 0.0177(4) Uani 1 1 d . . .
S4 S -0.0037(2) 0.34992(17) 0.64820(10) 0.0173(4) Uani 1 1 d . . .
S8 S 0.0039(2) 0.81256(17) 0.14649(10) 0.0178(4) Uani 1 1 d . . .
S3 S 0.2984(2) 0.28800(16) 0.65826(10) 0.0154(4) Uani 1 1 d . . .
N2 N 0.2141(6) 0.4399(5) 0.7586(3) 0.0144(13) Uani 1 1 d . . .
N1 N 0.3755(7) 0.3693(5) 0.3927(3) 0.0155(13) Uani 1 1 d . . .
N4 N 0.2037(6) 0.9071(5) 0.2640(3) 0.0117(12) Uani 1 1 d . . .
C7 C 0.3647(8) 0.4574(6) 0.7995(4) 0.0148(15) Uani 1 1 d . . .
H7A H 0.4293 0.4386 0.7634 0.018 Uiso 1 1 calc R . .
H7B H 0.3907 0.5415 0.8180 0.018 Uiso 1 1 calc R . .
C14 C 0.3724(9) 1.0301(6) -0.1078(4) 0.0209(17) Uani 1 1 d . . .
H14A H 0.4583 1.0890 -0.1025 0.025 Uiso 1 1 calc R . .
H14B H 0.3075 1.0591 -0.0748 0.025 Uiso 1 1 calc R . .
C17 C 0.3490(8) 0.9271(6) 0.3109(4) 0.0154(15) Uani 1 1 d . . .
H17A H 0.3674 1.0094 0.3337 0.018 Uiso 1 1 calc R . .
H17B H 0.4213 0.9165 0.2777 0.018 Uiso 1 1 calc R . .
C11 C 0.3251(8) 0.8367(6) -0.0524(4) 0.0157(16) Uani 1 1 d . . .
N3 N 0.4135(7) 0.9147(5) -0.0834(3) 0.0175(14) Uani 1 1 d . . .
C8 C 0.3871(9) 0.3833(7) 0.8648(4) 0.0218(17) Uani 1 1 d . . .
H8A H 0.4865 0.3988 0.8887 0.033 Uiso 1 1 calc R . .
H8B H 0.3641 0.2997 0.8469 0.033 Uiso 1 1 calc R . .
H8C H 0.3255 0.4027 0.9015 0.033 Uiso 1 1 calc R . .
C10 C 0.1141(9) 0.6379(7) 0.7650(5) 0.0254(19) Uani 1 1 d . . .
H10A H 0.0477 0.6809 0.7888 0.038 Uiso 1 1 calc R . .
H10B H 0.0864 0.6315 0.7102 0.038 Uiso 1 1 calc R . .
H10C H 0.2102 0.6804 0.7780 0.038 Uiso 1 1 calc R . .
C18 C 0.3643(9) 0.8427(8) 0.3737(4) 0.0261(19) Uani 1 1 d . . .
H18A H 0.4602 0.8589 0.4024 0.039 Uiso 1 1 calc R . .
H18B H 0.3479 0.7611 0.3514 0.039 Uiso 1 1 calc R . .
H18C H 0.2945 0.8542 0.4074 0.039 Uiso 1 1 calc R . .
C19 C 0.0946(8) 0.9712(6) 0.2942(4) 0.0150(15) Uani 1 1 d . . .
H19A H 0.1138 0.9779 0.3499 0.018 Uiso 1 1 calc R . .
H19B H -0.0004 0.9254 0.2784 0.018 Uiso 1 1 calc R . .
C1 C 0.2866(8) 0.3101(6) 0.4331(4) 0.0143(15) Uani 1 1 d . . .
C16 C 0.1741(8) 0.8375(6) 0.1996(4) 0.0139(15) Uani 1 1 d . . .
C9 C 0.1109(8) 0.5097(7) 0.7940(4) 0.0165(16) Uani 1 1 d . . .
H9A H 0.1366 0.5162 0.8495 0.020 Uiso 1 1 calc R . .
H9B H 0.0135 0.4671 0.7811 0.020 Uiso 1 1 calc R . .
C2 C 0.5114(8) 0.3238(7) 0.3757(4) 0.0192(17) Uani 1 1 d . . .
H2A H 0.5286 0.3445 0.3249 0.023 Uiso 1 1 calc R . .
H2B H 0.4992 0.2368 0.3754 0.023 Uiso 1 1 calc R . .
C12 C 0.5553(9) 0.8872(7) -0.0985(4) 0.0261(19) Uani 1 1 d . . .
H12A H 0.5940 0.8385 -0.0590 0.031 Uiso 1 1 calc R . .
H12B H 0.6205 0.9618 -0.0948 0.031 Uiso 1 1 calc R . .
C4 C 0.3463(9) 0.4869(6) 0.3618(4) 0.0198(17) Uani 1 1 d . . .
H4A H 0.4366 0.5404 0.3665 0.024 Uiso 1 1 calc R . .
H4B H 0.2826 0.5242 0.3920 0.024 Uiso 1 1 calc R . .
C5 C 0.2770(8) 0.4694(7) 0.2785(4) 0.0207(17) Uani 1 1 d . . .
H5A H 0.2601 0.5459 0.2602 0.031 Uiso 1 1 calc R . .
H5B H 0.1865 0.4179 0.2739 0.031 Uiso 1 1 calc R . .
H5C H 0.3403 0.4332 0.2484 0.031 Uiso 1 1 calc R . .
C15 C 0.2982(9) 1.0172(7) -0.1908(4) 0.0243(18) Uani 1 1 d . . .
H15A H 0.2717 1.0935 -0.2052 0.037 Uiso 1 1 calc R . .
H15B H 0.2127 0.9594 -0.1961 0.037 Uiso 1 1 calc R . .
H15C H 0.3632 0.9905 -0.2237 0.037 Uiso 1 1 calc R . .
C13 C 0.5526(9) 0.8214(7) -0.1765(4) 0.0240(18) Uani 1 1 d . . .
H13A H 0.6489 0.8065 -0.1826 0.036 Uiso 1 1 calc R . .
H13B H 0.5166 0.8697 -0.2161 0.036 Uiso 1 1 calc R . .
H13C H 0.4906 0.7462 -0.1802 0.036 Uiso 1 1 calc R . .
C20 C 0.0946(8) 1.0973(7) 0.2655(4) 0.0201(17) Uani 1 1 d . . .
H20A H 0.0216 1.1365 0.2860 0.030 Uiso 1 1 calc R . .
H20B H 0.0746 1.0908 0.2104 0.030 Uiso 1 1 calc R . .
H20C H 0.1878 1.1434 0.2821 0.030 Uiso 1 1 calc R . .
C6 C 0.1725(8) 0.3669(6) 0.6956(4) 0.0140(15) Uani 1 1 d . . .
C3 C 0.6421(9) 0.3758(7) 0.4341(4) 0.030(2) Uani 1 1 d . . .
H3A H 0.7269 0.3449 0.4208 0.044 Uiso 1 1 calc R . .
H3B H 0.6268 0.3534 0.4843 0.044 Uiso 1 1 calc R . .
H3C H 0.6552 0.4619 0.4342 0.044 Uiso 1 1 calc R . .

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 0.01535(17) 0.01143(15) 0.01070(15) -0.00025(11) 0.00110(11) -0.00066(11)
Bi2 0.01459(17) 0.01168(15) 0.01038(15) -0.00064(11) 0.00163(11) -0.00117(11)
I1 0.0185(3) 0.0152(2) 0.0171(2) 0.00178(19) 0.00139(19) 0.0013(2)
I2 0.0185(3) 0.0196(3) 0.0188(2) 0.0018(2) -0.00143(19) 0.0020(2)
S7 0.0134(9) 0.0174(9) 0.0127(8) -0.0019(7) 0.0027(7) 0.0022(7)
S2 0.0174(10) 0.0148(9) 0.0172(9) 0.0038(7) 0.0028(7) 0.0021(7)
S1 0.0219(10) 0.0136(9) 0.0122(8) 0.0012(7) 0.0026(7) 0.0034(7)
S6 0.0201(10) 0.0138(9) 0.0201(9) 0.0039(8) 0.0063(8) 0.0014(8)
S5 0.0208(10) 0.0191(9) 0.0146(9) 0.0024(8) 0.0041(7) 0.0055(8)
S4 0.0129(10) 0.0215(10) 0.0163(9) -0.0030(8) -0.0009(7) 0.0026(8)
S8 0.0131(10) 0.0253(10) 0.0140(9) -0.0017(8) -0.0001(7) 0.0030(8)
S3 0.0129(9) 0.0180(9) 0.0148(8) -0.0038(7) 0.0016(7) 0.0030(7)
N2 0.013(3) 0.017(3) 0.012(3) 0.000(3) 0.000(2) 0.003(3)
N1 0.021(4) 0.013(3) 0.011(3) -0.004(2) 0.000(2) 0.002(3)
N4 0.013(3) 0.012(3) 0.011(3) 0.001(2) 0.003(2) 0.002(2)
C7 0.013(4) 0.014(4) 0.018(4) -0.002(3) 0.003(3) 0.002(3)
C14 0.031(5) 0.014(4) 0.017(4) 0.003(3) 0.008(3) -0.002(3)
C17 0.012(4) 0.015(4) 0.018(4) -0.001(3) 0.003(3) 0.001(3)
C11 0.022(4) 0.014(4) 0.009(3) -0.003(3) 0.001(3) -0.005(3)
N3 0.020(4) 0.017(3) 0.014(3) 0.001(3) 0.003(3) -0.004(3)
C8 0.020(4) 0.026(4) 0.020(4) 0.003(3) 0.002(3) 0.009(3)
C10 0.022(5) 0.018(4) 0.036(5) -0.004(4) 0.004(4) 0.006(3)
C18 0.021(5) 0.037(5) 0.020(4) -0.001(4) 0.004(3) 0.006(4)
C19 0.011(4) 0.019(4) 0.015(4) -0.003(3) 0.004(3) 0.002(3)
C1 0.018(4) 0.013(4) 0.009(3) -0.005(3) 0.001(3) -0.005(3)
C16 0.016(4) 0.011(3) 0.014(3) 0.010(3) 0.000(3) 0.001(3)
C9 0.014(4) 0.021(4) 0.015(4) -0.005(3) 0.002(3) 0.005(3)
C2 0.022(4) 0.020(4) 0.015(4) 0.002(3) 0.004(3) 0.001(3)
C12 0.019(4) 0.029(5) 0.028(4) -0.006(4) 0.007(3) -0.005(4)
C4 0.029(5) 0.009(4) 0.022(4) 0.003(3) 0.006(3) 0.003(3)
C5 0.023(4) 0.019(4) 0.021(4) 0.008(3) 0.003(3) 0.007(3)
C15 0.020(4) 0.032(5) 0.023(4) 0.004(4) 0.002(3) 0.009(4)
C13 0.028(5) 0.022(4) 0.025(4) 0.001(3) 0.012(3) 0.003(3)
C20 0.014(4) 0.023(4) 0.023(4) -0.006(3) 0.005(3) 0.002(3)
C6 0.020(4) 0.009(3) 0.013(3) 0.004(3) 0.002(3) 0.000(3)
C3 0.031(5) 0.022(4) 0.032(5) -0.004(4) -0.006(4) 0.005(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 S3 2.6406(18) . ?
Bi1 S2 2.6651(18) . ?
Bi1 S1 2.6880(18) . ?
Bi1 S4 2.8467(18) . ?
Bi1 I1 3.2682(6) . ?
Bi1 I1 3.3639(5) 2_556 ?
Bi2 S6 2.6433(18) . ?
Bi2 S7 2.6669(17) . ?
Bi2 S8 2.7605(18) . ?
Bi2 S5 2.7739(18) . ?
Bi2 I2 3.2438(6) . ?
Bi2 I2 3.3438(6) 2_565 ?
I1 Bi1 3.3640(5) 2_556 ?
I2 Bi2 3.3437(6) 2_565 ?
S7 C16 1.748(8) . ?
S2 C1 1.729(8) . ?
S1 C1 1.731(8) . ?
S6 C11 1.757(8) . ?
S5 C11 1.705(8) . ?
S4 C6 1.730(8) . ?
S8 C16 1.718(7) . ?
S3 C6 1.739(7) . ?
N2 C6 1.321(9) . ?
N2 C7 1.481(9) . ?
N2 C9 1.496(9) . ?
N1 C1 1.320(9) . ?
N1 C2 1.493(9) . ?
N1 C4 1.500(9) . ?
N4 C16 1.313(9) . ?
N4 C19 1.462(9) . ?
N4 C17 1.478(9) . ?
C7 C8 1.469(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 N3 1.469(10) . ?
C14 C15 1.520(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C17 C18 1.506(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C11 N3 1.330(9) . ?
N3 C12 1.461(10) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 C9 1.556(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.533(10) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 C3 1.519(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 C13 1.516(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 C5 1.511(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
S3 Bi1 S2 94.69(6) . . ?
S3 Bi1 S1 85.26(5) . . ?
S2 Bi1 S1 67.60(6) . . ?
S3 Bi1 S4 65.89(5) . . ?
S2 Bi1 S4 87.72(5) . . ?
S1 Bi1 S4 140.56(5) . . ?
S3 Bi1 I1 88.84(4) . . ?
S2 Bi1 I1 144.18(4) . . ?
S1 Bi1 I1 77.24(4) . . ?
S4 Bi1 I1 125.60(4) . . ?
S3 Bi1 I1 170.62(4) . 2_556 ?
S2 Bi1 I1 87.40(4) . 2_556 ?
S1 Bi1 I1 103.96(4) . 2_556 ?
S4 Bi1 I1 105.13(4) . 2_556 ?
I1 Bi1 I1 94.815(14) . 2_556 ?
S6 Bi2 S7 94.98(6) . . ?
S6 Bi2 S8 86.96(6) . . ?
S7 Bi2 S8 66.59(5) . . ?
S6 Bi2 S5 66.92(6) . . ?
S7 Bi2 S5 84.78(5) . . ?
S8 Bi2 S5 139.57(5) . . ?
S6 Bi2 I2 89.93(4) . . ?
S7 Bi2 I2 156.53(4) . . ?
S8 Bi2 I2 90.84(4) . . ?
S5 Bi2 I2 118.09(4) . . ?
S6 Bi2 I2 149.68(4) . 2_565 ?
S7 Bi2 I2 93.16(4) . 2_565 ?
S8 Bi2 I2 122.94(4) . 2_565 ?
S5 Bi2 I2 84.86(4) . 2_565 ?
I2 Bi2 I2 94.081(14) . 2_565 ?
Bi1 I1 Bi1 85.184(13) . 2_556 ?
Bi2 I2 Bi2 85.919(14) . 2_565 ?
C16 S7 Bi2 88.5(2) . . ?
C1 S2 Bi1 86.9(2) . . ?
C1 S1 Bi1 86.1(2) . . ?
C11 S6 Bi2 88.1(2) . . ?
C11 S5 Bi2 84.9(2) . . ?
C6 S4 Bi1 84.3(2) . . ?
C16 S8 Bi2 86.1(2) . . ?
C6 S3 Bi1 90.8(2) . . ?
C6 N2 C7 122.6(6) . . ?
C6 N2 C9 122.0(6) . . ?
C7 N2 C9 115.4(5) . . ?
C1 N1 C2 122.0(6) . . ?
C1 N1 C4 121.8(6) . . ?
C2 N1 C4 116.2(6) . . ?
C16 N4 C19 122.2(6) . . ?
C16 N4 C17 122.7(6) . . ?
C19 N4 C17 115.1(5) . . ?
C8 C7 N2 113.7(6) . . ?
C8 C7 H7A 108.8 . . ?
N2 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N2 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N3 C14 C15 111.1(6) . . ?
N3 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N3 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N4 C17 C18 112.5(6) . . ?
N4 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
N4 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
N3 C11 S5 121.6(6) . . ?
N3 C11 S6 119.0(6) . . ?
S5 C11 S6 119.4(4) . . ?
C11 N3 C12 121.4(7) . . ?
C11 N3 C14 122.5(7) . . ?
C12 N3 C14 116.1(6) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 C20 111.6(5) . . ?
N4 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
N4 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
N1 C1 S2 120.7(6) . . ?
N1 C1 S1 120.5(6) . . ?
S2 C1 S1 118.8(4) . . ?
N4 C16 S8 122.3(6) . . ?
N4 C16 S7 119.1(5) . . ?
S8 C16 S7 118.6(4) . . ?
N2 C9 C10 111.2(6) . . ?
N2 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N1 C2 C3 112.2(6) . . ?
N1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N3 C12 C13 113.9(6) . . ?
N3 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N3 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N1 C4 C5 111.3(6) . . ?
N1 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C6 S4 121.6(6) . . ?
N2 C6 S3 119.3(6) . . ?
S4 C6 S3 119.1(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.035
_refine_diff_density_min         -1.544
_refine_diff_density_rms         0.296
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1445039'
_audit_update_record             
;
2016-01-03 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 Bi Br N2 S4'
_chemical_formula_sum            'C6 H12 Bi Br N2 S4'
_chemical_formula_weight         529.31

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   10.2109(5)
_cell_length_b                   16.3665(7)
_cell_length_c                   8.2545(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.026(4)
_cell_angle_gamma                90.00
_cell_volume                     1354.00(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(6)
_cell_measurement_reflns_used    4194
_cell_measurement_theta_min      3.1790
_cell_measurement_theta_max      28.8220

_exptl_crystal_description       rods
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    16.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8252
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2370
_reflns_number_gt                2136
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0301P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2370
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.24653(2) 0.210395(13) 0.17552(2) 0.01274(10) Uani 1 1 d . . .
Br1 Br 0.03421(6) 0.24097(4) -0.11465(7) 0.01616(15) Uani 1 1 d . . .
S1 S 0.53297(16) 0.23172(10) 0.19125(18) 0.0194(3) Uani 1 1 d . . .
S2 S 0.35025(15) 0.13079(9) -0.05020(17) 0.0152(3) Uani 1 1 d . . .
S4 S 0.10315(15) 0.07303(9) 0.17678(17) 0.0168(3) Uani 1 1 d . . .
S3 S 0.33944(15) 0.11215(9) 0.43498(18) 0.0183(3) Uani 1 1 d . . .
C2 C 0.5943(7) 0.0719(4) -0.1600(7) 0.0268(16) Uani 1 1 d . . .
H2A H 0.6798 0.0572 -0.1836 0.040 Uiso 1 1 calc R . .
H2B H 0.5406 0.0962 -0.2561 0.040 Uiso 1 1 calc R . .
H2C H 0.5507 0.0239 -0.1297 0.040 Uiso 1 1 calc R . .
N2 N 0.1866(5) -0.0181(3) 0.4413(6) 0.0222(12) Uani 1 1 d . . .
C3 C 0.7510(6) 0.1592(5) 0.0319(8) 0.0290(16) Uani 1 1 d . . .
H3A H 0.8087 0.1290 -0.0254 0.043 Uiso 1 1 calc R . .
H3B H 0.7778 0.1505 0.1485 0.043 Uiso 1 1 calc R . .
H3C H 0.7566 0.2163 0.0079 0.043 Uiso 1 1 calc R . .
N1 N 0.6128(5) 0.1311(3) -0.0225(6) 0.0209(12) Uani 1 1 d . . .
C1 C 0.5116(6) 0.1620(4) 0.0352(7) 0.0142(13) Uani 1 1 d . . .
C4 C 0.2058(6) 0.0485(4) 0.3607(7) 0.0178(14) Uani 1 1 d . . .
C5 C 0.0801(8) -0.0759(4) 0.3802(9) 0.0369(19) Uani 1 1 d . . .
H5A H 0.0832 -0.1201 0.4573 0.055 Uiso 1 1 calc R . .
H5B H 0.0917 -0.0970 0.2753 0.055 Uiso 1 1 calc R . .
H5C H -0.0045 -0.0488 0.3679 0.055 Uiso 1 1 calc R . .
C6 C 0.2763(8) -0.0416(4) 0.5978(8) 0.0380(19) Uani 1 1 d . . .
H6A H 0.2455 -0.0917 0.6379 0.057 Uiso 1 1 calc R . .
H6B H 0.2761 0.0007 0.6783 0.057 Uiso 1 1 calc R . .
H6C H 0.3653 -0.0489 0.5784 0.057 Uiso 1 1 calc R . .

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 0.01282(17) 0.01386(15) 0.01152(14) -0.00031(8) 0.00230(10) 0.00059(8)
Br1 0.0126(4) 0.0203(3) 0.0151(3) 0.0025(2) 0.0014(2) -0.0008(2)
S1 0.0152(9) 0.0237(8) 0.0191(8) -0.0054(7) 0.0028(6) -0.0020(6)
S2 0.0133(9) 0.0180(8) 0.0146(7) -0.0029(6) 0.0035(6) 0.0016(6)
S4 0.0152(9) 0.0165(8) 0.0176(8) -0.0014(6) 0.0005(6) -0.0013(6)
S3 0.0167(9) 0.0184(8) 0.0181(8) 0.0030(6) -0.0010(6) -0.0005(6)
C2 0.023(4) 0.032(4) 0.027(4) -0.005(3) 0.010(3) 0.012(3)
N2 0.032(4) 0.012(3) 0.022(3) 0.003(2) 0.005(2) -0.006(2)
C3 0.009(4) 0.050(5) 0.029(4) 0.006(3) 0.007(3) 0.006(3)
N1 0.016(3) 0.027(3) 0.020(3) -0.001(2) 0.005(2) 0.004(2)
C1 0.007(3) 0.017(3) 0.018(3) 0.005(2) 0.003(2) 0.006(2)
C4 0.013(3) 0.022(3) 0.018(3) -0.004(3) 0.002(3) 0.003(3)
C5 0.047(5) 0.024(4) 0.039(4) -0.002(3) 0.009(4) -0.015(3)
C6 0.054(5) 0.034(4) 0.022(4) 0.014(3) -0.003(3) -0.003(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 S2 2.6543(14) . ?
Bi1 S4 2.6839(15) . ?
Bi1 S3 2.7009(15) . ?
Bi1 S1 2.9237(16) . ?
Bi1 Br1 2.9497(6) . ?
Bi1 Br1 3.1257(6) 4_566 ?
Br1 Bi1 3.1256(6) 4_565 ?
S1 C1 1.703(6) . ?
S2 C1 1.740(6) . ?
S4 C4 1.720(6) . ?
S3 C4 1.733(6) . ?
C2 N1 1.476(8) . ?
N2 C4 1.311(8) . ?
N2 C5 1.456(8) . ?
N2 C6 1.484(7) . ?
C3 N1 1.470(8) . ?
N1 C1 1.319(7) . ?

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
S2 Bi1 S4 83.27(5) . . ?
S2 Bi1 S3 97.91(5) . . ?
S4 Bi1 S3 66.89(4) . . ?
S2 Bi1 S1 63.88(4) . . ?
S4 Bi1 S1 129.91(5) . . ?
S3 Bi1 S1 80.74(5) . . ?
S2 Bi1 Br1 80.98(3) . . ?
S4 Bi1 Br1 80.13(3) . . ?
S3 Bi1 Br1 146.83(4) . . ?
S1 Bi1 Br1 126.12(3) . . ?
S2 Bi1 Br1 157.84(3) . 4_566 ?
S4 Bi1 Br1 76.97(3) . 4_566 ?
S3 Bi1 Br1 83.56(4) . 4_566 ?
S1 Bi1 Br1 137.64(3) . 4_566 ?
Br1 Bi1 Br1 85.804(16) . 4_566 ?
Bi1 Br1 Bi1 90.759(17) . 4_565 ?
C1 S1 Bi1 84.5(2) . . ?
C1 S2 Bi1 92.60(19) . . ?
C4 S4 Bi1 87.6(2) . . ?
C4 S3 Bi1 86.8(2) . . ?
C4 N2 C5 122.6(5) . . ?
C4 N2 C6 122.0(5) . . ?
C5 N2 C6 115.4(5) . . ?
C1 N1 C3 122.9(5) . . ?
C1 N1 C2 122.4(5) . . ?
C3 N1 C2 114.4(5) . . ?
N1 C1 S1 122.3(5) . . ?
N1 C1 S2 119.2(5) . . ?
S1 C1 S2 118.5(3) . . ?
N2 C4 S4 121.1(5) . . ?
N2 C4 S3 120.3(4) . . ?
S4 C4 S3 118.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.643
_refine_diff_density_min         -1.433
_refine_diff_density_rms         0.207
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1445040'
_audit_update_record             
;
2016-01-03 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H20 Bi I N2 S4'
_chemical_formula_sum            'C10 H20 Bi I N2 S4'
_chemical_formula_weight         632.40

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c


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                   11.845(5)
_cell_length_b                   18.266(5)
_cell_length_c                   8.659(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 106.904(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1792.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.2(7)
_cell_measurement_reflns_used    4007
_cell_measurement_theta_min      2.8583
_cell_measurement_theta_max      28.9723

_exptl_crystal_description       rods
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    12.011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11153
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3152
_reflns_number_gt                2664
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0177P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3152
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4559(6) 0.1672(4) 0.0584(8) 0.0183(17) Uani 1 1 d . . .
C2 C 0.2405(6) 0.1710(4) -0.0123(9) 0.0227(18) Uani 1 1 d . . .
H2A H 0.2524 0.1868 0.0983 0.027 Uiso 1 1 calc R . .
H2B H 0.1800 0.1334 -0.0356 0.027 Uiso 1 1 calc R . .
C3 C 0.1963(7) 0.2358(5) -0.1244(11) 0.046(3) Uani 1 1 d . . .
H3A H 0.1247 0.2542 -0.1082 0.069 Uiso 1 1 calc R . .
H3B H 0.1815 0.2203 -0.2344 0.069 Uiso 1 1 calc R . .
H3C H 0.2550 0.2737 -0.1011 0.069 Uiso 1 1 calc R . .
C4 C 0.3404(7) 0.0721(4) -0.1267(9) 0.029(2) Uani 1 1 d . . .
H4A H 0.2747 0.0433 -0.1146 0.035 Uiso 1 1 calc R . .
H4B H 0.4114 0.0430 -0.0868 0.035 Uiso 1 1 calc R . .
C5 C 0.3213(11) 0.0874(5) -0.3036(10) 0.069(4) Uani 1 1 d . . .
H5A H 0.3151 0.0420 -0.3612 0.104 Uiso 1 1 calc R . .
H5B H 0.3867 0.1150 -0.3172 0.104 Uiso 1 1 calc R . .
H5C H 0.2499 0.1150 -0.3452 0.104 Uiso 1 1 calc R . .
C6 C 0.7708(6) 0.0895(4) 0.5373(8) 0.0148(16) Uani 1 1 d . . .
C7 C 0.7220(6) 0.0325(4) 0.7674(8) 0.0157(16) Uani 1 1 d . . .
H7A H 0.6831 0.0785 0.7756 0.019 Uiso 1 1 calc R . .
H7B H 0.7724 0.0199 0.8739 0.019 Uiso 1 1 calc R . .
C8 C 0.6293(7) -0.0272(4) 0.7080(9) 0.029(2) Uani 1 1 d . . .
H8A H 0.5831 -0.0320 0.7820 0.044 Uiso 1 1 calc R . .
H8B H 0.6678 -0.0729 0.7015 0.044 Uiso 1 1 calc R . .
H8C H 0.5787 -0.0144 0.6032 0.044 Uiso 1 1 calc R . .
C9 C 0.8999(6) -0.0061(4) 0.6877(8) 0.0148(16) Uani 1 1 d . . .
H9A H 0.9140 -0.0189 0.5862 0.018 Uiso 1 1 calc R . .
H9B H 0.8855 -0.0510 0.7387 0.018 Uiso 1 1 calc R . .
C10 C 1.0085(6) 0.0315(4) 0.7960(9) 0.0228(18) Uani 1 1 d . . .
H10A H 1.0752 -0.0007 0.8139 0.034 Uiso 1 1 calc R . .
H10B H 0.9955 0.0432 0.8975 0.034 Uiso 1 1 calc R . .
H10C H 1.0236 0.0756 0.7451 0.034 Uiso 1 1 calc R . .
N1 N 0.3517(5) 0.1387(3) -0.0265(7) 0.0155(13) Uani 1 1 d . . .
N2 N 0.7945(5) 0.0412(3) 0.6555(7) 0.0157(14) Uani 1 1 d . . .
S1 S 0.58304(16) 0.12564(10) 0.0383(2) 0.0187(4) Uani 1 1 d . . .
S2 S 0.46767(16) 0.23999(10) 0.1812(2) 0.0187(4) Uani 1 1 d . . .
S3 S 0.64562(15) 0.14525(10) 0.5038(2) 0.0149(4) Uani 1 1 d . . .
S4 S 0.85512(16) 0.09822(10) 0.4082(2) 0.0168(4) Uani 1 1 d . . .
Bi1 Bi 0.71588(2) 0.210768(14) 0.26774(3) 0.01369(9) Uani 1 1 d . . .
I1 I 0.89987(4) 0.18987(3) 0.05636(5) 0.01805(13) Uani 1 1 d . . .

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
C1 0.017(4) 0.020(4) 0.021(4) 0.003(3) 0.010(3) -0.004(3)
C2 0.013(4) 0.028(5) 0.027(4) 0.004(4) 0.006(3) -0.003(4)
C3 0.025(5) 0.063(7) 0.044(6) 0.030(5) 0.001(4) 0.016(5)
C4 0.028(5) 0.028(5) 0.030(5) -0.010(4) 0.007(4) -0.014(4)
C5 0.144(12) 0.041(6) 0.027(6) -0.022(5) 0.032(7) -0.044(7)
C6 0.011(4) 0.014(4) 0.018(4) -0.005(3) 0.003(3) -0.001(3)
C7 0.016(4) 0.019(4) 0.013(4) -0.003(3) 0.006(3) -0.006(3)
C8 0.022(5) 0.040(5) 0.024(5) 0.005(4) 0.005(4) -0.013(4)
C9 0.011(4) 0.017(4) 0.015(4) 0.005(3) 0.002(3) 0.004(3)
C10 0.018(4) 0.027(5) 0.020(4) -0.006(4) 0.001(3) -0.001(4)
N1 0.011(3) 0.020(3) 0.015(3) -0.007(3) 0.002(3) -0.002(3)
N2 0.012(3) 0.021(4) 0.015(3) 0.002(3) 0.006(3) -0.002(3)
S1 0.0149(10) 0.0219(11) 0.0197(10) -0.0108(9) 0.0053(8) -0.0049(8)
S2 0.0127(9) 0.0186(10) 0.0226(10) -0.0038(9) 0.0016(8) 0.0002(8)
S3 0.0102(9) 0.0166(10) 0.0183(10) 0.0022(8) 0.0049(8) 0.0027(8)
S4 0.0151(10) 0.0193(10) 0.0187(10) 0.0027(8) 0.0093(8) 0.0044(8)
Bi1 0.01205(15) 0.01468(16) 0.01333(16) 0.00027(12) 0.00210(11) -0.00074(11)
I1 0.0128(3) 0.0225(3) 0.0193(3) 0.0041(2) 0.0053(2) 0.0030(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
C1 N1 1.344(9) . ?
C1 S2 1.683(7) . ?
C1 S1 1.740(7) . ?
C2 N1 1.480(9) . ?
C2 C3 1.524(10) . ?
C4 N1 1.477(9) . ?
C4 C5 1.508(10) . ?
C6 N2 1.319(8) . ?
C6 S4 1.709(7) . ?
C6 S3 1.751(7) . ?
C7 N2 1.478(8) . ?
C7 C8 1.527(9) . ?
C9 N2 1.476(8) . ?
C9 C10 1.518(9) . ?
S1 Bi1 2.6502(19) . ?
S2 Bi1 2.865(2) . ?
S3 Bi1 2.700(2) . ?
S4 Bi1 2.6943(19) . ?
Bi1 I1 3.2504(12) . ?
Bi1 I1 3.3350(11) 4_566 ?
I1 Bi1 3.3349(11) 4_565 ?

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
N1 C1 S2 123.1(6) . . ?
N1 C1 S1 117.4(5) . . ?
S2 C1 S1 119.5(4) . . ?
N1 C2 C3 113.9(6) . . ?
N1 C4 C5 113.9(7) . . ?
N2 C6 S4 122.5(5) . . ?
N2 C6 S3 119.8(5) . . ?
S4 C6 S3 117.7(4) . . ?
N2 C7 C8 110.7(5) . . ?
N2 C9 C10 111.8(6) . . ?
C1 N1 C4 123.5(6) . . ?
C1 N1 C2 119.9(6) . . ?
C4 N1 C2 116.5(6) . . ?
C6 N2 C9 121.0(6) . . ?
C6 N2 C7 123.2(6) . . ?
C9 N2 C7 115.8(5) . . ?
C1 S1 Bi1 90.7(2) . . ?
C1 S2 Bi1 84.7(3) . . ?
C6 S3 Bi1 87.2(2) . . ?
C6 S4 Bi1 88.2(2) . . ?
S1 Bi1 S4 92.46(6) . . ?
S1 Bi1 S3 93.49(7) . . ?
S4 Bi1 S3 66.61(6) . . ?
S1 Bi1 S2 64.71(6) . . ?
S4 Bi1 S2 135.00(6) . . ?
S3 Bi1 S2 76.23(6) . . ?
S1 Bi1 I1 81.84(5) . . ?
S4 Bi1 I1 75.05(5) . . ?
S3 Bi1 I1 141.16(4) . . ?
S2 Bi1 I1 132.81(5) . . ?
S1 Bi1 I1 175.79(4) . 4_566 ?
S4 Bi1 I1 84.03(5) . 4_566 ?
S3 Bi1 I1 87.25(5) . 4_566 ?
S2 Bi1 I1 119.47(4) . 4_566 ?
I1 Bi1 I1 94.98(4) . 4_566 ?
Bi1 I1 Bi1 87.65(4) . 4_565 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.563
_refine_diff_density_min         -1.529
_refine_diff_density_rms         0.223
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1445041'
_audit_update_record             
;
2016-01-03 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H6 Bi I2 N S2'
_chemical_formula_sum            'C3 H6 Bi I2 N S2'
_chemical_formula_weight         582.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   23.8005(12)
_cell_length_b                   11.1504(6)
_cell_length_c                   8.0446(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.625(5)
_cell_angle_gamma                90.00
_cell_volume                     2132.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.3(5)
_cell_measurement_reflns_used    4326
_cell_measurement_theta_min      3.7151
_cell_measurement_theta_max      72.3630

_exptl_crystal_description       polygones
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2016
_exptl_absorpt_coefficient_mu    81.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (cU) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6546
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.72
_diffrn_reflns_theta_max         67.00
_reflns_number_total             1914
_reflns_number_gt                1854
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0924P)²+4.7003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1914
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1380(4) 0.3816(7) 0.2428(11) 0.0091(16) Uani 1 1 d . . .
C2 C 0.2084(4) 0.5202(8) 0.3649(12) 0.0183(18) Uani 1 1 d . . .
H2A H 0.2134 0.6056 0.3683 0.027 Uiso 1 1 calc R . .
H2B H 0.2398 0.4839 0.3132 0.027 Uiso 1 1 calc R . .
H2C H 0.2062 0.4900 0.4762 0.027 Uiso 1 1 calc R . .
C3 C 0.1233(4) 0.5946(8) 0.2019(12) 0.0200(19) Uani 1 1 d . . .
H3A H 0.1424 0.6677 0.2325 0.030 Uiso 1 1 calc R . .
H3B H 0.0867 0.5944 0.2472 0.030 Uiso 1 1 calc R . .
H3C H 0.1195 0.5889 0.0828 0.030 Uiso 1 1 calc R . .
N1 N 0.1561(3) 0.4910(7) 0.2684(9) 0.0158(15) Uani 1 1 d . . .
S004 S 0.07510(9) 0.35512(16) 0.1339(3) 0.0121(4) Uani 1 1 d . . .
S005 S 0.17531(8) 0.25691(17) 0.3189(3) 0.0131(4) Uani 1 1 d . . .
Bi1 Bi 0.090388(12) 0.12531(2) 0.19365(4) 0.0092(2) Uani 1 1 d . . .
I1 I 0.03249(2) 0.16310(4) 0.52396(6) 0.0101(2) Uani 1 1 d . . .
I2 I 0.16215(2) 0.08752(4) -0.11142(6) 0.0106(2) Uani 1 1 d . . .

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
C1 0.008(4) 0.006(4) 0.012(4) -0.004(3) 0.003(3) 0.001(3)
C2 0.018(4) 0.014(4) 0.023(5) -0.003(4) -0.001(4) -0.008(4)
C3 0.030(5) 0.006(4) 0.024(5) 0.000(4) -0.001(4) 0.001(4)
N1 0.015(4) 0.011(3) 0.021(4) -0.001(3) -0.001(3) -0.003(3)
S004 0.0110(10) 0.0053(8) 0.0196(11) 0.0013(8) -0.0029(8) 0.0014(7)
S005 0.0093(9) 0.0081(9) 0.0217(9) -0.0032(8) -0.0010(7) 0.0007(7)
Bi1 0.0076(3) 0.0039(3) 0.0161(3) -0.00055(10) -0.00072(17) -0.00136(10)
I1 0.0072(3) 0.0066(3) 0.0164(3) -0.00020(18) -0.0013(2) 0.00020(18)
I2 0.0089(3) 0.0062(3) 0.0168(3) -0.00168(19) 0.0002(2) -0.00083(18)

_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
C1 N1 1.307(11) . ?
C1 S004 1.725(10) . ?
C1 S005 1.745(9) . ?
C2 N1 1.474(11) . ?
C3 N1 1.480(12) . ?
S004 Bi1 2.6295(19) . ?
S005 Bi1 2.658(2) . ?
Bi1 I1 3.0777(6) . ?
Bi1 I2 3.0824(6) . ?
Bi1 I2 3.2806(6) 6_556 ?
Bi1 I1 3.3655(6) 2 ?
I1 Bi1 3.3655(6) 2 ?
I2 Bi1 3.2806(6) 6 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S004 120.8(7) . . ?
N1 C1 S005 122.0(7) . . ?
S004 C1 S005 117.3(5) . . ?
C1 N1 C2 123.6(8) . . ?
C1 N1 C3 120.4(8) . . ?
C2 N1 C3 115.9(7) . . ?
C1 S004 Bi1 87.9(3) . . ?
C1 S005 Bi1 86.6(3) . . ?
S004 Bi1 S005 68.15(6) . . ?
S004 Bi1 I1 87.75(5) . . ?
S005 Bi1 I1 87.70(5) . . ?
S004 Bi1 I2 93.71(5) . . ?
S005 Bi1 I2 86.44(5) . . ?
I1 Bi1 I2 172.939(18) . . ?
S004 Bi1 I2 148.99(5) . 6_556 ?
S005 Bi1 I2 81.25(5) . 6_556 ?
I1 Bi1 I2 85.998(14) . 6_556 ?
I2 Bi1 I2 89.219(14) . 6_556 ?
S004 Bi1 I1 70.92(5) . 2 ?
S005 Bi1 I1 139.08(4) . 2 ?
I1 Bi1 I1 91.099(16) . 2 ?
I2 Bi1 I1 95.909(16) . 2 ?
I2 Bi1 I1 139.480(15) 6_556 2 ?
Bi1 I1 Bi1 86.935(15) . 2 ?
Bi1 I2 Bi1 100.613(16) . 6 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.960
_refine_diff_density_min         -2.855
_refine_diff_density_rms         0.629
