# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_AU20_a
_database_code_depnum_ccdc_archive 'CCDC 1566485'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_AU20_a              
;
PROBLEM: Check Calcd Residual Density  0.54A From     Bi2      -4.87 eA-3
RESPONSE: Residual density without any chemical sense.
;
_vrf_PLAT974_AU20_a              
;
PROBLEM: Check Calcd Negative Residual Density on     Bi1      -4.32 eA-3
RESPONSE: Residual density without any chemical sense.
;
_vrf_PLAT971_AU20_a              
;
PROBLEM: Check Calcd Residual Density  0.91A From     Bi2       3.43 eA-3
RESPONSE: Residual density without any chemical sense.
;
_vrf_PLAT972_AU20_a_2            
;
PROBLEM: Check Calcd Residual Density  0.08A From      I2      -3.49 eA-3
RESPONSE: Residual density without any chemical sense.
;
# Added during the CSD deposition process: Thursday 03 August 2017 08:24 AM
# end Validation Reply Form

#complex 1 (Mepy)[Bi3I9]
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 Bi3 I10 N'
_chemical_formula_weight         1990.07

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   10.8976(3)
_cell_length_b                   11.2977(3)
_cell_length_c                   23.3163(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.257(3)
_cell_angle_gamma                90
_cell_volume                     2840.89(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4632
_cell_measurement_theta_min      3.7750
_cell_measurement_theta_max      29.2130

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    4.653
_exptl_crystal_F_000             3320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    29.398
_shelx_estimated_absorpt_T_min   0.067
_shelx_estimated_absorpt_T_max   0.321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.14296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            7228
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.521
_diffrn_reflns_theta_max         29.553
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3399
_reflns_number_gt                3056
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (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)+(0.0711P)²] 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         3399
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 0.5123(11) 0.4847(12) 0.7016(6) 0.023(3) Uani 1 1 d . . . . .
H1A H 0.5201 0.5284 0.6675 0.028 Uiso 1 1 calc R U . . .
C2 C 0.5000 0.6724(15) 0.7500 0.037(5) Uani 1 2 d S T P . .
H2A H 0.5099 0.7013 0.7113 0.056 Uiso 0.5 1 calc R U P . .
H2B H 0.4214 0.7013 0.7604 0.056 Uiso 0.5 1 calc R U P . .
H2C H 0.5688 0.7013 0.7783 0.056 Uiso 0.5 1 calc R U P . .
C3 C 0.5138(11) 0.3629(11) 0.7010(7) 0.027(3) Uani 1 1 d . . . . .
H3A H 0.5245 0.3217 0.6665 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5000 0.3016(16) 0.7500 0.029(4) Uani 1 2 d S T P . .
H4A H 0.5000 0.2175 0.7500 0.035 Uiso 1 2 calc R U P . .
N1 N 0.5000 0.5393(11) 0.7500 0.012(3) Uani 1 2 d S T P . .
I1 I 0.33862(6) 0.86383(6) 0.61917(3) 0.01647(18) Uani 1 1 d . . . . .
I2 I 0.00166(6) 0.68859(6) 0.53963(3) 0.01286(17) Uani 1 1 d . . . . .
I3 I 0.34690(6) 0.50560(6) 0.54535(3) 0.01551(18) Uani 1 1 d . . . . .
I4 I 0.21247(7) 0.19473(6) 0.62214(4) 0.0205(2) Uani 1 1 d . . . . .
I5 I 0.16689(7) 0.51762(8) 0.70818(4) 0.0255(2) Uani 1 1 d . . . . .
Bi1 Bi 0.2500 0.7500 0.5000 0.01310(15) Uani 1 2 d S . P . .
Bi2 Bi 0.10906(4) 0.42303(3) 0.59373(2) 0.01373(14) 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
C1 N1 1.310(14) . ?
C1 C3 1.376(18) . ?
C1 H1A 0.9500 . ?
C2 N1 1.50(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.363(16) . ?
C3 H3A 0.9500 . ?
C4 C3 1.363(17) 2_656 ?
C4 H4A 0.9500 . ?
N1 C1 1.310(14) 2_656 ?
I1 Bi1 3.0880(7) . ?
I1 Bi2 3.1603(7) 3 ?
I2 Bi1 3.0623(6) . ?
I2 Bi2 3.3967(8) . ?
I2 Bi2 3.4113(8) 5_566 ?
I3 Bi1 3.0881(6) . ?
I3 Bi2 3.1145(8) . ?
I4 Bi2 2.8543(8) . ?
I5 Bi2 2.8597(9) . ?
Bi1 I2 3.0622(6) 7_566 ?
Bi1 I1 3.0880(7) 7_566 ?
Bi1 I3 3.0881(6) 7_566 ?
Bi2 I1 3.1603(7) 3_445 ?
Bi2 I2 3.4112(9) 5_566 ?

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 C3 118.9(12) . . ?
N1 C1 H1A 120.5 . . ?
C3 C1 H1A 120.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C1 119.7(13) . . ?
C4 C3 H3A 120.1 . . ?
C1 C3 H3A 120.1 . . ?
C3 C4 C3 118.9(17) 2_656 . ?
C3 C4 H4A 120.5 2_656 . ?
C3 C4 H4A 120.5 . . ?
C1 N1 C1 123.7(15) 2_656 . ?
C1 N1 C2 118.1(7) 2_656 . ?
C1 N1 C2 118.1(7) . . ?
Bi1 I1 Bi2 95.67(2) . 3 ?
Bi1 I2 Bi2 92.284(17) . . ?
Bi1 I2 Bi2 91.201(19) . 5_566 ?
Bi2 I2 Bi2 94.008(19) . 5_566 ?
Bi1 I3 Bi2 97.492(19) . . ?
I2 Bi1 I2 180.0 7_566 . ?
I2 Bi1 I1 89.921(19) 7_566 7_566 ?
I2 Bi1 I1 90.080(19) . 7_566 ?
I2 Bi1 I1 90.080(19) 7_566 . ?
I2 Bi1 I1 89.919(19) . . ?
I1 Bi1 I1 180.00(3) 7_566 . ?
I2 Bi1 I3 88.145(18) 7_566 7_566 ?
I2 Bi1 I3 91.855(18) . 7_566 ?
I1 Bi1 I3 90.97(2) 7_566 7_566 ?
I1 Bi1 I3 89.03(2) . 7_566 ?
I2 Bi1 I3 91.854(18) 7_566 . ?
I2 Bi1 I3 88.146(18) . . ?
I1 Bi1 I3 89.03(2) 7_566 . ?
I1 Bi1 I3 90.97(2) . . ?
I3 Bi1 I3 179.998(10) 7_566 . ?
I4 Bi2 I5 95.42(3) . . ?
I4 Bi2 I3 91.91(2) . . ?
I5 Bi2 I3 98.21(3) . . ?
I4 Bi2 I1 96.49(2) . 3_445 ?
I5 Bi2 I1 89.45(2) . 3_445 ?
I3 Bi2 I1 168.07(2) . 3_445 ?
I4 Bi2 I2 171.05(3) . . ?
I5 Bi2 I2 91.98(2) . . ?
I3 Bi2 I2 82.025(19) . . ?
I1 Bi2 I2 88.61(2) 3_445 . ?
I4 Bi2 I2 87.34(2) . 5_566 ?
I5 Bi2 I2 172.08(2) . 5_566 ?
I3 Bi2 I2 89.11(2) . 5_566 ?
I1 Bi2 I2 82.85(2) 3_445 5_566 ?
I2 Bi2 I2 85.992(19) . 5_566 ?

_refine_diff_density_max         2.779
_refine_diff_density_min         -4.450
_refine_diff_density_rms         0.611


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_AU91_a
_database_code_depnum_ccdc_archive 'CCDC 1566490'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_AU91_a              
;
PROBLEM: Check Calcd Residual Density  0.80A From     Bi1      -4.05 eA-3
RESPONSE: Residual density without any chemical sense
;
_vrf_PLAT971_AU91_a              
;
PROBLEM: Check Calcd Residual Density  0.89A From     Bi1       2.89 eA-3
RESPONSE: Residual density without any chemical sense
;
_vrf_PLAT972_AU91_a_2            
;
PROBLEM: Check Calcd Residual Density  0.66A From     Bi1      -2.93 eA-3
RESPONSE: Residual density without any chemical sense
;
# Added during the CSD deposition process: Thursday 03 August 2017 08:24 AM
# end Validation Reply Form

#complex 6 (Me-i-quinolinium){[BiI4]}
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Bi I4 N'
_chemical_formula_weight         860.77

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.6749(3)
_cell_length_b                   10.0389(4)
_cell_length_c                   11.4778(5)
_cell_angle_alpha                71.809(4)
_cell_angle_beta                 84.837(3)
_cell_angle_gamma                83.290(3)
_cell_volume                     833.04(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3282
_cell_measurement_theta_min      3.6860
_cell_measurement_theta_max      29.2270

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.432
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    17.973
_shelx_estimated_absorpt_T_min   0.174
_shelx_estimated_absorpt_T_max   0.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.13940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            6579
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.343
_diffrn_reflns_theta_max         29.576
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3863
_reflns_number_gt                3419
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (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)+(0.0375P)²] 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         3863
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4046(13) 1.3454(11) 0.1366(10) 0.034(3) Uani 1 1 d . . . . .
H1A H 0.3864 1.3444 0.2224 0.051 Uiso 1 1 calc R U . . .
H1B H 0.5304 1.3452 0.1124 0.051 Uiso 1 1 calc R U . . .
H1C H 0.3414 1.4303 0.0840 0.051 Uiso 1 1 calc R U . . .
C2 C 0.2693(11) 1.1224(10) 0.2237(8) 0.021(2) Uani 1 1 d . . . . .
H2A H 0.2645 1.1380 0.3014 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3484(10) 1.1979(9) 0.0135(8) 0.0185(19) Uani 1 1 d . . . . .
H3A H 0.3982 1.2653 -0.0555 0.022 Uiso 1 1 calc R U . . .
C4 C 0.2078(11) 1.0041(10) 0.2157(8) 0.0203(19) Uani 1 1 d . . . . .
H4A H 0.1580 0.9396 0.2868 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2887(10) 1.0795(9) -0.0024(8) 0.0145(17) Uani 1 1 d . . . . .
C6 C 0.2183(10) 0.9779(9) 0.1017(8) 0.0175(19) Uani 1 1 d . . . . .
C7 C 0.1576(11) 0.8563(10) 0.0860(9) 0.023(2) Uani 1 1 d . . . . .
H7A H 0.1087 0.7875 0.1543 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1699(11) 0.8393(11) -0.0275(10) 0.030(3) Uani 1 1 d . . . . .
H8A H 0.1311 0.7573 -0.0375 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2389(11) 0.9405(11) -0.1300(9) 0.027(2) Uani 1 1 d . . . . .
H9A H 0.2444 0.9257 -0.2081 0.033 Uiso 1 1 calc R U . . .
C10 C 0.2988(11) 1.0603(11) -0.1208(8) 0.022(2) Uani 1 1 d . . . . .
H10A H 0.3454 1.1280 -0.1910 0.026 Uiso 1 1 calc R U . . .
N1 N 0.3380(9) 1.2196(8) 0.1228(7) 0.0184(16) Uani 1 1 d . . . . .
I1 I 0.43100(7) 0.59797(6) 0.31297(5) 0.01637(14) Uani 1 1 d . . . . .
I2 I 0.92069(7) 0.47638(6) 0.17018(5) 0.01981(14) Uani 1 1 d . . . . .
I3 I 0.65437(8) 0.15239(6) 0.44416(5) 0.02106(15) Uani 1 1 d . . . . .
I4 I 1.11074(7) 0.27873(6) 0.54563(5) 0.01843(14) Uani 1 1 d . . . . .
Bi1 Bi 0.77322(4) 0.42212(3) 0.42594(3) 0.01312(10) 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
C1 N1 1.474(11) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.359(12) . ?
C2 N1 1.370(11) . ?
C2 H2A 0.9500 . ?
C3 N1 1.332(11) . ?
C3 C5 1.392(12) . ?
C3 H3A 0.9500 . ?
C4 C6 1.408(12) . ?
C4 H4A 0.9500 . ?
C5 C6 1.418(12) . ?
C5 C10 1.425(12) . ?
C6 C7 1.423(12) . ?
C7 C8 1.359(13) . ?
C7 H7A 0.9500 . ?
C8 C9 1.401(15) . ?
C8 H8A 0.9500 . ?
C9 C10 1.373(13) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
I1 Bi1 3.1299(6) . ?
I1 Bi1 3.2138(6) 2_666 ?
I2 Bi1 2.9569(6) . ?
I3 Bi1 2.8977(7) . ?
I4 Bi1 3.0339(6) . ?
I4 Bi1 3.3478(7) 2_766 ?
Bi1 I1 3.2138(6) 2_666 ?
Bi1 I4 3.3479(7) 2_766 ?

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 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 N1 121.9(8) . . ?
C4 C2 H2A 119.1 . . ?
N1 C2 H2A 119.1 . . ?
N1 C3 C5 121.9(8) . . ?
N1 C3 H3A 119.0 . . ?
C5 C3 H3A 119.0 . . ?
C2 C4 C6 119.6(8) . . ?
C2 C4 H4A 120.2 . . ?
C6 C4 H4A 120.2 . . ?
C3 C5 C6 118.6(8) . . ?
C3 C5 C10 120.7(8) . . ?
C6 C5 C10 120.7(8) . . ?
C4 C6 C5 118.1(8) . . ?
C4 C6 C7 123.0(9) . . ?
C5 C6 C7 118.9(8) . . ?
C8 C7 C6 119.5(9) . . ?
C8 C7 H7A 120.2 . . ?
C6 C7 H7A 120.2 . . ?
C7 C8 C9 121.3(9) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C10 C9 C8 121.9(9) . . ?
C10 C9 H9A 119.0 . . ?
C8 C9 H9A 119.0 . . ?
C9 C10 C5 117.7(9) . . ?
C9 C10 H10A 121.1 . . ?
C5 C10 H10A 121.1 . . ?
C3 N1 C2 119.8(8) . . ?
C3 N1 C1 120.4(8) . . ?
C2 N1 C1 119.8(8) . . ?
Bi1 I1 Bi1 94.684(16) . 2_666 ?
Bi1 I4 Bi1 92.930(16) . 2_766 ?
I3 Bi1 I2 95.076(19) . . ?
I3 Bi1 I4 91.065(18) . . ?
I2 Bi1 I4 95.771(17) . . ?
I3 Bi1 I1 94.708(18) . . ?
I2 Bi1 I1 86.377(17) . . ?
I4 Bi1 I1 173.645(18) . . ?
I3 Bi1 I1 88.167(18) . 2_666 ?
I2 Bi1 I1 171.305(18) . 2_666 ?
I4 Bi1 I1 92.226(16) . 2_666 ?
I1 Bi1 I1 85.316(16) . 2_666 ?
I3 Bi1 I4 170.483(19) . 2_766 ?
I2 Bi1 I4 94.397(18) . 2_766 ?
I4 Bi1 I4 87.070(16) . 2_766 ?
I1 Bi1 I4 86.802(16) . 2_766 ?
I1 Bi1 I4 82.585(17) 2_666 2_766 ?

_refine_diff_density_max         2.827
_refine_diff_density_min         -4.081
_refine_diff_density_rms         0.382


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2

####################################################################### 
# 
# 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_AU30_a
_database_code_depnum_ccdc_archive 'CCDC 1566487'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
#complex 3 (Etpy)[Bi3I9]
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H10 Bi3 I10 N'
_chemical_formula_weight         2004.10

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6530(2)
_cell_length_b                   27.2277(6)
_cell_length_c                   14.2784(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.354(2)
_cell_angle_gamma                90
_cell_volume                     2962.26(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5571
_cell_measurement_theta_min      3.6550
_cell_measurement_theta_max      29.1210

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    4.494
_exptl_crystal_F_000             3352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    28.196
_shelx_estimated_absorpt_T_min   0.165
_shelx_estimated_absorpt_T_max   0.333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            15177
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.275
_diffrn_reflns_theta_max         29.550
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6958
_reflns_number_gt                5735
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (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)+(0.0181P)²] 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         6958
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0543
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Bi1 Bi 0.21326(3) 0.48859(2) 0.74648(2) 0.01490(7) Uani 1 1 d . . . . .
C1 C -0.1497(10) 0.1875(3) 0.5496(6) 0.0258(19) Uani 1 1 d . . . . .
H1A H -0.1336 0.2147 0.5096 0.031 Uiso 1 1 calc R U . . .
I10 I 0.10443(7) 0.22714(2) 0.80129(4) 0.02629(13) Uani 1 1 d . . . . .
I1 I 0.10439(6) 0.54225(2) 0.90322(4) 0.02356(12) Uani 1 1 d . . . . .
N1 N -0.2882(8) 0.1510(2) 0.6732(5) 0.0228(15) Uani 1 1 d . . . . .
Bi2 Bi 0.71091(3) 0.39999(2) 0.70826(2) 0.01362(7) Uani 1 1 d . . . . .
I2 I 0.33595(7) 0.57067(2) 0.64751(4) 0.02434(12) Uani 1 1 d . . . . .
C2 C -0.2623(10) 0.1901(3) 0.6177(6) 0.0253(19) Uani 1 1 d . . . . .
H2A H -0.3237 0.2198 0.6264 0.030 Uiso 1 1 calc R U . . .
C3 C -0.0587(10) 0.1437(3) 0.5402(6) 0.0236(19) Uani 1 1 d . . . . .
H3A H 0.0221 0.1408 0.4939 0.028 Uiso 1 1 calc R U . . .
Bi3 Bi 0.20737(3) 0.30741(2) 0.68923(2) 0.01433(7) Uani 1 1 d . . . . .
I3 I 0.56184(6) 0.46353(2) 0.86337(3) 0.01627(10) Uani 1 1 d . . . . .
I4 I 0.85222(6) 0.49174(2) 0.62137(4) 0.02001(11) Uani 1 1 d . . . . .
C4 C -0.0856(10) 0.1047(3) 0.5980(6) 0.0250(19) Uani 1 1 d . . . . .
H4A H -0.0245 0.0747 0.5915 0.030 Uiso 1 1 calc R U . . .
I5 I 1.04467(6) 0.38605(2) 0.84615(3) 0.01545(10) Uani 1 1 d . . . . .
C5 C -0.2011(10) 0.1092(3) 0.6649(6) 0.0228(18) Uani 1 1 d . . . . .
H5A H -0.2192 0.0825 0.7055 0.027 Uiso 1 1 calc R U . . .
I6 I 0.36347(6) 0.40993(2) 0.58540(3) 0.01471(10) Uani 1 1 d . . . . .
C6 C -0.4243(11) 0.1554(3) 0.7434(7) 0.040(3) Uani 1 1 d . . . . .
H6A H -0.4814 0.1880 0.7372 0.048 Uiso 1 1 calc R U . . .
H6B H -0.5159 0.1300 0.7301 0.048 Uiso 1 1 calc R U . . .
I7 I 0.85171(6) 0.33147(2) 0.56440(3) 0.01637(11) Uani 1 1 d . . . . .
C7 C -0.3398(13) 0.1491(4) 0.8416(7) 0.051(3) Uani 1 1 d . . . . .
H7A H -0.4291 0.1520 0.8863 0.077 Uiso 1 1 calc R U . . .
H7B H -0.2848 0.1166 0.8479 0.077 Uiso 1 1 calc R U . . .
H7C H -0.2504 0.1745 0.8550 0.077 Uiso 1 1 calc R U . . .
I9 I 0.31046(6) 0.24984(2) 0.53621(4) 0.02458(12) Uani 1 1 d . . . . .
I8 I 0.56965(6) 0.30465(2) 0.79961(3) 0.01563(10) 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
Bi1 I2 2.8496(5) . ?
Bi1 I1 2.8611(6) . ?
Bi1 I3 3.0883(6) . ?
Bi1 I4 3.1482(6) 1_455 ?
Bi1 I6 3.4192(5) . ?
C1 C2 1.361(10) . ?
C1 C3 1.394(10) . ?
C1 H1A 0.9500 . ?
I10 Bi3 2.8621(5) . ?
N1 C5 1.330(9) . ?
N1 C2 1.351(9) . ?
N1 C6 1.516(9) . ?
Bi2 I4 3.0331(5) . ?
Bi2 I7 3.0454(5) . ?
Bi2 I6 3.0578(5) . ?
Bi2 I5 3.0993(6) . ?
Bi2 I3 3.1098(5) . ?
Bi2 I8 3.1418(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.372(10) . ?
C3 H3A 0.9500 . ?
Bi3 I9 2.8591(5) . ?
Bi3 I8 3.0595(5) . ?
Bi3 I7 3.1796(6) 1_455 ?
Bi3 I5 3.4171(5) 1_455 ?
Bi3 I6 3.4276(5) . ?
I4 Bi1 3.1482(6) 1_655 ?
C4 C5 1.366(10) . ?
C4 H4A 0.9500 . ?
I5 Bi3 3.4171(5) 1_655 ?
C5 H5A 0.9500 . ?
C6 C7 1.498(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
I7 Bi3 3.1796(6) 1_655 ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 Bi1 I1 96.947(17) . . ?
I2 Bi1 I3 97.664(16) . . ?
I1 Bi1 I3 89.427(16) . . ?
I2 Bi1 I4 90.554(16) . 1_455 ?
I1 Bi1 I4 97.222(16) . 1_455 ?
I3 Bi1 I4 168.752(16) . 1_455 ?
I2 Bi1 I6 90.611(15) . . ?
I1 Bi1 I6 170.659(17) . . ?
I3 Bi1 I6 84.111(13) . . ?
I4 Bi1 I6 88.152(14) 1_455 . ?
C2 C1 C3 117.9(7) . . ?
C2 C1 H1A 121.0 . . ?
C3 C1 H1A 121.0 . . ?
C5 N1 C2 121.2(6) . . ?
C5 N1 C6 120.5(6) . . ?
C2 N1 C6 118.2(6) . . ?
I4 Bi2 I7 93.817(15) . . ?
I4 Bi2 I6 90.948(14) . . ?
I7 Bi2 I6 90.616(14) . . ?
I4 Bi2 I5 93.239(14) . . ?
I7 Bi2 I5 91.776(14) . . ?
I6 Bi2 I5 175.029(15) . . ?
I4 Bi2 I3 90.092(15) . . ?
I7 Bi2 I3 176.009(16) . . ?
I6 Bi2 I3 90.122(14) . . ?
I5 Bi2 I3 87.195(14) . . ?
I4 Bi2 I8 179.223(16) . . ?
I7 Bi2 I8 86.043(14) . . ?
I6 Bi2 I8 89.818(14) . . ?
I5 Bi2 I8 86.001(14) . . ?
I3 Bi2 I8 90.038(14) . . ?
N1 C2 C1 121.1(7) . . ?
N1 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C4 C3 C1 120.0(7) . . ?
C4 C3 H3A 120.0 . . ?
C1 C3 H3A 120.0 . . ?
I9 Bi3 I10 96.812(17) . . ?
I9 Bi3 I8 94.521(15) . . ?
I10 Bi3 I8 88.671(16) . . ?
I9 Bi3 I7 88.130(16) . 1_455 ?
I10 Bi3 I7 101.819(16) . 1_455 ?
I8 Bi3 I7 168.819(15) . 1_455 ?
I9 Bi3 I5 171.120(17) . 1_455 ?
I10 Bi3 I5 88.614(15) . 1_455 ?
I8 Bi3 I5 92.621(14) . 1_455 ?
I7 Bi3 I5 83.869(13) 1_455 1_455 ?
I9 Bi3 I6 89.071(15) . . ?
I10 Bi3 I6 171.448(18) . . ?
I8 Bi3 I6 84.670(13) . . ?
I7 Bi3 I6 84.514(13) 1_455 . ?
I5 Bi3 I6 86.343(12) 1_455 . ?
Bi1 I3 Bi2 95.385(15) . . ?
Bi2 I4 Bi1 94.190(15) . 1_655 ?
C5 C4 C3 119.5(7) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
Bi2 I5 Bi3 89.389(14) . 1_655 ?
N1 C5 C4 120.2(7) . . ?
N1 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
Bi2 I6 Bi1 89.916(14) . . ?
Bi2 I6 Bi3 89.957(14) . . ?
Bi1 I6 Bi3 93.820(12) . . ?
C7 C6 N1 110.3(7) . . ?
C7 C6 H6A 109.6 . . ?
N1 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
N1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
Bi2 I7 Bi3 94.955(15) . 1_655 ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Bi3 I8 Bi2 95.526(15) . . ?

_refine_diff_density_max         1.377
_refine_diff_density_min         -1.584
_refine_diff_density_rms         0.277


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_AU113b_a
_database_code_depnum_ccdc_archive 'CCDC 1566488'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_AU113b_a            
;
PROBLEM: Check Calcd Residual Density  0.94A From    I007      -4.24 eA-3
RESPONSE: Residual density without any chemical sense
;
_vrf_PLAT972_AU113b_a_2          
;
PROBLEM: Check Calcd Residual Density  0.95A From    I007      -3.33 eA-3
RESPONSE: Residual density without any chemical sense
;
# Added during the CSD deposition process: Thursday 03 August 2017 08:24 AM
# end Validation Reply Form

#complex 4 (NC7H10)3Bi2I9*CH3CN
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H33 Bi2 I9 N4'
_chemical_formula_weight         1925.59

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   16.4361(4)
_cell_length_b                   22.9617(9)
_cell_length_c                   11.2234(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4235.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4274
_cell_measurement_theta_min      3.8100
_cell_measurement_theta_max      29.0460

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.020
_exptl_crystal_F_000             3368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    14.877
_shelx_estimated_absorpt_T_min   0.155
_shelx_estimated_absorpt_T_max   0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            14012
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.452
_diffrn_reflns_theta_max         29.557
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5268
_reflns_number_gt                4248
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (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)+(0.0336P)²+18.9353P] 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         5268
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.4267(5) 0.4136(3) 0.6549(8) 0.0349(19) Uani 1 1 d . . . . .
H1A H 0.4680 0.3829 0.6418 0.042 Uiso 1 1 calc R U . . .
H1B H 0.4526 0.4517 0.6385 0.042 Uiso 1 1 calc R U . . .
C2 C 0.4000(6) 0.4120(6) 0.7784(8) 0.071(4) Uani 1 1 d . . . . .
H2A H 0.4468 0.4179 0.8311 0.106 Uiso 1 1 calc R U . . .
H2B H 0.3599 0.4428 0.7921 0.106 Uiso 1 1 calc R U . . .
H2C H 0.3753 0.3740 0.7954 0.106 Uiso 1 1 calc R U . . .
C1S C 0.0466(6) 0.4573(4) 0.4666(9) 0.060(2) Uiso 0.5 1 d . . P . .
C3 C 0.3301(6) 0.3509(4) 0.5490(14) 0.082(5) Uani 1 1 d . . . . .
H3A H 0.3550 0.3188 0.5879 0.098 Uiso 1 1 calc R U . . .
C4 C 0.3223(6) 0.4498(5) 0.5195(9) 0.057(3) Uani 1 1 d . . . . .
H4A H 0.3408 0.4881 0.5363 0.068 Uiso 1 1 calc R U . . .
C5 C 0.2591(6) 0.4410(5) 0.4418(11) 0.075(4) Uani 1 1 d . . . . .
H5A H 0.2338 0.4737 0.4053 0.090 Uiso 1 1 calc R U . . .
C6 C 0.2319(5) 0.3872(4) 0.4161(7) 0.044(2) Uani 1 1 d . . . . .
H6A H 0.1893 0.3813 0.3603 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2674(7) 0.3414(5) 0.4724(12) 0.078(4) Uani 1 1 d . . . . .
H7A H 0.2485 0.3029 0.4583 0.093 Uiso 1 1 calc R U . . .
C11 C 0.0000 0.5000 0.5000 0.074(5) Uani 1 2 d S . P . .
N2 N 0.3572(3) 0.4047(3) 0.5705(6) 0.0287(14) Uani 1 1 d . . . . .
N1S N 0.0466(6) 0.4573(4) 0.4666(9) 0.060(2) Uiso 0.5 1 d . . P . .
I002 I 0.52682(3) 0.2500 0.59783(6) 0.01981(14) Uani 1 2 d S T P . .
I003 I 0.67043(4) 0.2500 0.28314(6) 0.02590(15) Uani 1 2 d S T P . .
I004 I 0.78281(4) 0.2500 0.63985(6) 0.02795(16) Uani 1 2 d S T P . .
I005 I 0.65251(3) 0.41638(2) 0.71646(4) 0.02810(12) Uani 1 1 d . . . . .
I006 I 0.54343(3) 0.40932(2) 0.36299(5) 0.03271(13) Uani 1 1 d . . . . .
I007 I 0.80141(3) 0.40941(3) 0.40280(5) 0.05048(18) Uani 1 1 d . . . . .
Bi01 Bi 0.66440(2) 0.34232(2) 0.50187(2) 0.02395(9) Uani 1 1 d . . . . .
N1A N 0.9662(6) 0.2643(4) 0.4232(10) 0.022(3) Uiso 0.5 1 d . . P A -1
C12 C 0.9260(8) 0.252(2) 0.2144(12) 0.047(5) Uani 0.5 1 d . . P A -1
H12A H 0.8875 0.2374 0.1551 0.070 Uiso 0.5 1 calc R U P A -1
H12B H 0.9302 0.2947 0.2068 0.070 Uiso 0.5 1 calc R U P A -1
H12C H 0.9796 0.2347 0.2010 0.070 Uiso 0.5 1 calc R U P A -1
C10 C 0.8971(8) 0.2372(8) 0.3356(13) 0.034(6) Uani 0.5 1 d . . P A -1
H10A H 0.8930 0.1945 0.3457 0.041 Uiso 0.5 1 calc R U P A -1
H10B H 0.8432 0.2549 0.3516 0.041 Uiso 0.5 1 calc R U P A -1
C8 C 0.9879(9) 0.2150(7) 0.4756(14) 0.027(3) Uiso 0.5 1 d . . P A -1
H8A H 0.9603 0.1799 0.4563 0.033 Uiso 0.5 1 calc R U P A -1
C16 C 1.0530(10) 0.2142(8) 0.5615(16) 0.035(4) Uiso 0.5 1 d . . P A -1
H16A H 1.0709 0.1790 0.5974 0.042 Uiso 0.5 1 calc R U P A -1
C14 C 1.0881(9) 0.2671(6) 0.5890(14) 0.033(4) Uiso 0.5 1 d . . P A -1
H14A H 1.1299 0.2692 0.6473 0.039 Uiso 0.5 1 calc R U P A -1
C13 C 1.0621(10) 0.3175(7) 0.5312(15) 0.033(4) Uiso 0.5 1 d . . P A -1
H13A H 1.0866 0.3538 0.5504 0.040 Uiso 0.5 1 calc R U P A -1
C15 C 1.0022(9) 0.3155(7) 0.4476(14) 0.030(3) Uiso 0.5 1 d . . P A -1
H15A H 0.9860 0.3499 0.4070 0.036 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.454(12) . ?
C1 N2 1.499(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1S C11 1.300(10) . ?
C3 N2 1.334(11) . ?
C3 C7 1.360(14) . ?
C3 H3A 0.9500 . ?
C4 N2 1.316(11) . ?
C4 C5 1.372(12) . ?
C4 H4A 0.9500 . ?
C5 C6 1.346(14) . ?
C5 H5A 0.9500 . ?
C6 C7 1.357(14) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C11 N1S 1.300(10) 5_566 ?
C11 C1S 1.300(10) 5_566 ?
I002 Bi01 3.2812(5) . ?
I002 Bi01 3.2812(5) 7_565 ?
I003 Bi01 3.2450(6) . ?
I003 Bi01 3.2451(6) 7_565 ?
I004 Bi01 3.2679(6) . ?
I004 Bi01 3.2679(6) 7_565 ?
I005 Bi01 2.9547(6) . ?
I006 Bi01 2.9580(6) . ?
I007 Bi01 2.9464(6) . ?
N1A C8 1.325(18) . ?
N1A C15 1.343(18) . ?
N1A C10 1.627(16) . ?
C12 C10 1.48(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 C16 1.44(2) . ?
C8 H8A 0.9500 . ?
C16 C14 1.38(2) . ?
C16 H16A 0.9500 . ?
C14 C13 1.39(2) . ?
C14 H14A 0.9500 . ?
C13 C15 1.36(2) . ?
C13 H13A 0.9500 . ?
C15 H15A 0.9500 . ?

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
C2 C1 N2 111.6(7) . . ?
C2 C1 H1A 109.3 . . ?
N2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C7 121.1(10) . . ?
N2 C3 H3A 119.5 . . ?
C7 C3 H3A 119.5 . . ?
N2 C4 C5 119.4(9) . . ?
N2 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C6 C5 C4 121.4(10) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C7 118.0(8) . . ?
C5 C6 H6A 121.0 . . ?
C7 C6 H6A 121.0 . . ?
C6 C7 C3 119.7(10) . . ?
C6 C7 H7A 120.2 . . ?
C3 C7 H7A 120.2 . . ?
C1S C11 N1S 180.0 . 5_566 ?
C1S C11 C1S 180.0 . 5_566 ?
N1S C11 C1S 0.0 5_566 5_566 ?
C4 N2 C3 120.3(8) . . ?
C4 N2 C1 119.9(7) . . ?
C3 N2 C1 119.7(7) . . ?
Bi01 I002 Bi01 80.489(16) . 7_565 ?
Bi01 I003 Bi01 81.576(18) . 7_565 ?
Bi01 I004 Bi01 80.886(17) . 7_565 ?
I007 Bi01 I005 93.283(18) . . ?
I007 Bi01 I006 92.460(18) . . ?
I005 Bi01 I006 94.919(16) . . ?
I007 Bi01 I003 91.874(18) . . ?
I005 Bi01 I003 174.059(16) . . ?
I006 Bi01 I003 87.801(16) . . ?
I007 Bi01 I004 93.603(18) . . ?
I005 Bi01 I004 91.517(16) . . ?
I006 Bi01 I004 170.890(15) . . ?
I003 Bi01 I004 85.212(15) . . ?
I007 Bi01 I002 171.256(19) . . ?
I005 Bi01 I002 93.365(15) . . ?
I006 Bi01 I002 92.622(15) . . ?
I003 Bi01 I002 81.218(15) . . ?
I004 Bi01 I002 80.549(14) . . ?
C8 N1A C15 122.6(12) . . ?
C8 N1A C10 97.4(10) . . ?
C15 N1A C10 140.0(12) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12 C10 N1A 103.9(15) . . ?
C12 C10 H10A 111.0 . . ?
N1A C10 H10A 111.0 . . ?
C12 C10 H10B 111.0 . . ?
N1A C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N1A C8 C16 120.5(14) . . ?
N1A C8 H8A 119.7 . . ?
C16 C8 H8A 119.7 . . ?
C14 C16 C8 116.6(16) . . ?
C14 C16 H16A 121.7 . . ?
C8 C16 H16A 121.7 . . ?
C16 C14 C13 119.9(15) . . ?
C16 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C15 C13 C14 120.9(16) . . ?
C15 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
N1A C15 C13 119.3(15) . . ?
N1A C15 H15A 120.4 . . ?
C13 C15 H15A 120.4 . . ?

_refine_diff_density_max         2.289
_refine_diff_density_min         -4.153
_refine_diff_density_rms         0.245


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_AU83_a
_database_code_depnum_ccdc_archive 'CCDC 1566489'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_AU83_a              
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      20.16 Check
RESPONSE: H-atoms of disordered Me-quinolinium were not refined and added directly to the composition
;
_vrf_PLAT971_AU83_a              
;
PROBLEM: Check Calcd Residual Density  0.82A From     Bi1       2.96 eA-3
RESPONSE: Residual density without any chemical sense
;
# Added during the CSD deposition process: Thursday 03 August 2017 08:24 AM
# end Validation Reply Form

#complex 5 (Me-quinolinium){[BiI4]} 
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Bi I4 N'
_chemical_formula_weight         860.77

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   7.6699(3)
_cell_length_b                   16.3360(7)
_cell_length_c                   13.1719(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.060(4)
_cell_angle_gamma                90
_cell_volume                     1650.10(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1639
_cell_measurement_theta_min      4.0490
_cell_measurement_theta_max      29.3580

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.465
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    18.147
_shelx_estimated_absorpt_T_min   0.068
_shelx_estimated_absorpt_T_max   0.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.17437
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            3744
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.940
_diffrn_reflns_theta_max         29.433
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1942
_reflns_number_gt                1865
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (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)+(0.0384P)²+8.2810P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1942
_refine_ls_number_parameters     88
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.082
_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
C1 C -0.2500 0.5976(7) 0.5000 0.024(2) Uani 1 2 d S TU P . .
C2 C -0.1869(10) 0.5540(6) 0.4184(7) 0.0332(17) Uani 1 1 d . U . . .
C3 C -0.1417(9) 0.3142(5) 0.3736(5) 0.0246(15) Uani 1 1 d . U . . .
C5 C -0.2500 0.4279(7) 0.5000 0.049(3) Uani 1 2 d S TU P . .
C6 C -0.1331(19) 0.4046(10) 0.3610(12) 0.028(3) Uani 0.5 1 d . U P . .
C9 C -0.2168(17) 0.2925(9) 0.4685(10) 0.017(2) Uani 0.5 1 d . U P . .
C10 C -0.1848(11) 0.4678(6) 0.4172(8) 0.049(2) Uani 1 1 d . U . . .
N1 N -0.2770(15) 0.3426(7) 0.5391(9) 0.020(2) Uani 0.5 1 d . U P . .
I1 I -0.57738(6) 0.93272(2) 0.36099(3) 0.01636(12) Uani 1 1 d . . . . .
I2 I -0.10554(6) 0.80074(3) 0.36512(3) 0.01939(13) Uani 1 1 d . . . . .
Bi1 Bi -0.2500 0.92269(2) 0.5000 0.01229(11) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(10) . ?
C1 C2 1.384(10) 2_456 ?
C2 C10 1.408(13) . ?
C3 N1 1.397(13) 2_456 ?
C3 C9 1.430(14) . ?
C3 C6 1.487(18) . ?
C5 C10 1.372(13) . ?
C5 C10 1.372(13) 2_456 ?
C5 N1 1.502(15) 2_456 ?
C5 N1 1.502(15) . ?
C6 C10 1.335(18) . ?
C6 N1 1.81(2) 2_456 ?
C9 N1 0.826(16) 2_456 ?
C9 C9 0.98(3) 2_456 ?
C9 N1 1.329(16) . ?
N1 C9 0.826(16) 2_456 ?
N1 N1 1.12(2) 2_456 ?
N1 C3 1.397(13) 2_456 ?
N1 C6 1.81(2) 2_456 ?
I1 Bi1 3.0846(4) . ?
I1 Bi1 3.2824(5) 5_476 ?
I2 Bi1 2.9027(5) . ?
Bi1 I2 2.9027(5) 2_456 ?
Bi1 I1 3.0846(5) 2_456 ?
Bi1 I1 3.2824(5) 5_476 ?
Bi1 I1 3.2824(5) 6_675 ?

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
C2 C1 C2 117.9(11) . 2_456 ?
C1 C2 C10 121.9(9) . . ?
N1 C3 C9 34.0(7) 2_456 . ?
N1 C3 C6 77.5(9) 2_456 . ?
C9 C3 C6 111.4(10) . . ?
C10 C5 C10 123.3(12) . 2_456 ?
C10 C5 N1 96.5(6) . 2_456 ?
C10 C5 N1 140.1(9) 2_456 2_456 ?
C10 C5 N1 140.2(9) . . ?
C10 C5 N1 96.5(6) 2_456 . ?
N1 C5 N1 43.7(9) 2_456 . ?
C10 C6 C3 133.7(14) . . ?
C10 C6 N1 84.7(11) . 2_456 ?
C3 C6 N1 49.0(7) . 2_456 ?
N1 C9 C9 94.2(13) 2_456 2_456 ?
N1 C9 N1 56.9(15) 2_456 . ?
C9 C9 N1 38.3(7) 2_456 . ?
N1 C9 C3 70.8(13) 2_456 . ?
C9 C9 C3 164.2(11) 2_456 . ?
N1 C9 C3 127.5(11) . . ?
C6 C10 C5 101.0(11) . . ?
C6 C10 C2 141.5(13) . . ?
C5 C10 C2 117.5(9) . . ?
C9 N1 N1 84.8(13) 2_456 2_456 ?
C9 N1 C9 47.5(14) 2_456 . ?
N1 N1 C9 38.3(7) 2_456 . ?
C9 N1 C3 75.2(13) 2_456 2_456 ?
N1 N1 C3 159.6(8) 2_456 2_456 ?
C9 N1 C3 122.5(10) . 2_456 ?
C9 N1 C5 152.4(16) 2_456 . ?
N1 N1 C5 68.2(5) 2_456 . ?
C9 N1 C5 106.2(9) . . ?
C3 N1 C5 131.1(9) 2_456 . ?
C9 N1 C6 128.4(16) 2_456 2_456 ?
N1 N1 C6 145.5(7) 2_456 2_456 ?
C9 N1 C6 175.9(11) . 2_456 ?
C3 N1 C6 53.5(7) 2_456 2_456 ?
C5 N1 C6 77.7(7) . 2_456 ?
Bi1 I1 Bi1 92.258(12) . 5_476 ?
I2 Bi1 I2 93.32(2) . 2_456 ?
I2 Bi1 I1 89.363(13) . . ?
I2 Bi1 I1 94.820(13) 2_456 . ?
I2 Bi1 I1 94.821(13) . 2_456 ?
I2 Bi1 I1 89.364(13) 2_456 2_456 ?
I1 Bi1 I1 173.909(19) . 2_456 ?
I2 Bi1 I1 176.169(13) . 5_476 ?
I2 Bi1 I1 89.427(13) 2_456 5_476 ?
I1 Bi1 I1 87.743(12) . 5_476 ?
I1 Bi1 I1 87.875(12) 2_456 5_476 ?
I2 Bi1 I1 89.425(13) . 6_675 ?
I2 Bi1 I1 176.171(13) 2_456 6_675 ?
I1 Bi1 I1 87.876(12) . 6_675 ?
I1 Bi1 I1 87.742(12) 2_456 6_675 ?
I1 Bi1 I1 87.961(17) 5_476 6_675 ?

_refine_diff_density_max         2.843
_refine_diff_density_min         -2.452
_refine_diff_density_rms         0.302


_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_sq
_database_code_depnum_ccdc_archive 'CCDC 1566486'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2018-12-06 downloaded from the CCDC.
;
#complex 2 (NC6H8)3[Bi2I9]*CH3CN
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 Bi2 I9 N3'
_chemical_formula_weight         1842.46

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.5976(8)
_cell_length_b                   23.0812(13)
_cell_length_c                   11.0806(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3989.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6507
_cell_measurement_theta_min      3.8720
_cell_measurement_theta_max      29.2080

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.068
_exptl_crystal_F_000             3184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    15.788
_shelx_estimated_absorpt_T_min   0.129
_shelx_estimated_absorpt_T_max   0.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            13234
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.478
_diffrn_reflns_theta_max         29.522
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4797
_reflns_number_gt                4278
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0249P)²+5.1565P] 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         4797
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5008(4) 0.1992(3) 0.0700(6) 0.0455(19) Uani 1 1 d . . . . .
H1A H 0.4834 0.1639 0.1065 0.055 Uiso 1 1 calc R U . . .
I1 I 0.67493(3) 0.2500 0.28443(4) 0.01773(11) Uani 1 2 d S T P . .
Bi1 Bi 0.66063(2) 0.34132(2) 0.50535(2) 0.01710(6) Uani 1 1 d . . . . .
N1 N 0.4763(4) 0.2500 0.1173(6) 0.0349(19) Uani 1 2 d S T P . .
C2 C 0.5512(5) 0.1984(5) -0.0314(6) 0.062(3) Uani 1 1 d . . . . .
H2A H 0.5689 0.1625 -0.0651 0.074 Uiso 1 1 calc R U . . .
I2 I 0.51450(3) 0.2500 0.59292(4) 0.02200(12) Uani 1 2 d S T P . .
N2 N 0.8479(3) 0.4071(3) 0.8914(5) 0.0319(13) Uani 1 1 d . . . . .
C3 C 0.5763(7) 0.2500 -0.0843(8) 0.064(4) Uani 1 2 d S T P . .
H3A H 0.6102 0.2500 -0.1556 0.077 Uiso 1 2 calc R U P . .
I3 I 0.79093(3) 0.2500 0.63548(4) 0.02375(12) Uani 1 2 d S T P . .
C4 C 0.8230(4) 0.3526(3) 0.9177(7) 0.045(2) Uani 1 1 d . . . . .
H4A H 0.8409 0.3216 0.8672 0.054 Uiso 1 1 calc R U . . .
I4 I 0.64719(2) 0.41506(2) 0.72216(3) 0.02340(9) Uani 1 1 d . . . . .
C5 C 0.8231(4) 0.4501(3) 0.9611(6) 0.0379(16) Uani 1 1 d . . . . .
H5A H 0.8400 0.4886 0.9421 0.046 Uiso 1 1 calc R U . . .
I5 I 0.80694(2) 0.40842(2) 0.41146(3) 0.02617(10) Uani 1 1 d . . . . .
C6 C 0.7735(4) 0.4401(3) 1.0606(6) 0.0378(16) Uani 1 1 d . . . . .
H6A H 0.7577 0.4714 1.1117 0.045 Uiso 1 1 calc R U . . .
I6 I 0.52983(2) 0.40739(2) 0.37172(3) 0.02835(10) Uani 1 1 d . . . . .
C7 C 0.7465(5) 0.3854(3) 1.0868(6) 0.0444(18) Uani 1 1 d . . . . .
H7A H 0.7101 0.3783 1.1539 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7730(6) 0.3412(3) 1.0145(6) 0.047(2) Uani 1 1 d . . . . .
H8A H 0.7564 0.3025 1.0321 0.056 Uiso 1 1 calc R U . . .
C9 C 0.9006(5) 0.4202(4) 0.7844(7) 0.068(3) Uani 1 1 d . . . . .
H9A H 0.9139 0.3841 0.7416 0.102 Uiso 1 1 calc R U . . .
H9B H 0.8689 0.4462 0.7305 0.102 Uiso 1 1 calc R U . . .
H9C H 0.9540 0.4389 0.8098 0.102 Uiso 1 1 calc R U . . .
C10 C 0.4250(5) 0.2500 0.2271(8) 0.037(2) Uani 1 2 d S T P . .
H10A H 0.4121 0.2100 0.2505 0.056 Uiso 0.5 1 calc R U P . .
H10B H 0.4570 0.2691 0.2920 0.056 Uiso 0.5 1 calc R U P . .
H10C H 0.3713 0.2710 0.2127 0.056 Uiso 0.5 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(8) . ?
C1 C2 1.371(10) . ?
C1 H1A 0.9500 . ?
I1 Bi1 3.2380(4) . ?
I1 Bi1 3.2380(4) 7_565 ?
Bi1 I6 2.9462(4) . ?
Bi1 I5 2.9476(4) . ?
Bi1 I4 2.9517(4) . ?
Bi1 I2 3.2526(4) . ?
Bi1 I3 3.2639(4) . ?
N1 C1 1.340(8) 7_565 ?
N1 C10 1.456(10) . ?
C2 C3 1.385(10) . ?
C2 H2A 0.9500 . ?
I2 Bi1 3.2526(4) 7_565 ?
N2 C5 1.316(8) . ?
N2 C4 1.348(9) . ?
N2 C9 1.474(9) . ?
C3 C2 1.385(10) 7_565 ?
C3 H3A 0.9500 . ?
I3 Bi1 3.2638(4) 7_565 ?
C4 C8 1.353(11) . ?
C4 H4A 0.9500 . ?
C5 C6 1.367(9) . ?
C5 H5A 0.9500 . ?
C6 C7 1.361(9) . ?
C6 H6A 0.9500 . ?
C7 C8 1.361(10) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 119.9(8) . . ?
N1 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
Bi1 I1 Bi1 81.229(13) . 7_565 ?
I6 Bi1 I5 94.981(13) . . ?
I6 Bi1 I4 93.522(12) . . ?
I5 Bi1 I4 92.253(12) . . ?
I6 Bi1 I1 90.268(12) . . ?
I5 Bi1 I1 91.254(11) . . ?
I4 Bi1 I1 174.596(12) . . ?
I6 Bi1 I2 90.005(12) . . ?
I5 Bi1 I2 171.223(12) . . ?
I4 Bi1 I2 94.651(12) . . ?
I1 Bi1 I2 81.484(11) . . ?
I6 Bi1 I3 170.928(12) . . ?
I5 Bi1 I3 90.753(12) . . ?
I4 Bi1 I3 93.270(11) . . ?
I1 Bi1 I3 82.570(11) . . ?
I2 Bi1 I3 83.456(12) . . ?
C1 N1 C1 122.0(8) 7_565 . ?
C1 N1 C10 119.0(4) 7_565 . ?
C1 N1 C10 119.0(4) . . ?
C1 C2 C3 119.7(9) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
Bi1 I2 Bi1 80.789(13) . 7_565 ?
C5 N2 C4 119.5(6) . . ?
C5 N2 C9 118.8(7) . . ?
C4 N2 C9 121.7(7) . . ?
C2 C3 C2 118.8(10) 7_565 . ?
C2 C3 H3A 120.6 7_565 . ?
C2 C3 H3A 120.6 . . ?
Bi1 I3 Bi1 80.454(13) 7_565 . ?
N2 C4 C8 121.3(7) . . ?
N2 C4 H4A 119.4 . . ?
C8 C4 H4A 119.4 . . ?
N2 C5 C6 120.7(6) . . ?
N2 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 120.3(6) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C8 C7 C6 118.4(7) . . ?
C8 C7 H7A 120.8 . . ?
C6 C7 H7A 120.8 . . ?
C4 C8 C7 119.7(7) . . ?
C4 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.929
_refine_diff_density_min         -1.720
_refine_diff_density_rms         0.261



_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
