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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1444434'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '2,6 diisopropylanilinium tetraiodobismuthate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi I4, C12 H20 N '
_chemical_formula_sum            'C12 H20 Bi I4 N'
_chemical_formula_weight         894.87

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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.363(2)
_cell_length_b                   24.704(3)
_cell_length_c                   9.8942(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4244.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3021
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.51

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      2.801
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    2.801
_exptl_crystal_F_000             3152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    14.117
_shelx_estimated_absorpt_T_min   0.226
_shelx_estimated_absorpt_T_max   0.333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.226
_exptl_absorpt_correction_T_max  0.333
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            9045
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3730
_reflns_number_gt                2991
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.996

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.059(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3730
_refine_ls_number_parameters     169
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0606
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_restrained_S_all      0.872
_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 0.3401(10) 0.0000 0.5000 0.047(5) Uani 1 2 d S T P . .
C2 C 0.3750(9) 0.0442(5) 0.5496(13) 0.063(4) Uani 1 1 d D . . . .
C3 C 0.4583(10) 0.0436(8) 0.547(2) 0.116(8) Uani 1 1 d . . . . .
H3 H 0.4855 0.0736 0.5779 0.140 Uiso 1 1 calc R U . . .
C4 C 0.4969(19) 0.0000 0.5000 0.17(2) Uani 1 2 d S T P . .
H4 H 0.5505 0.0000 0.5000 0.203 Uiso 1 2 calc R U P . .
C5 C 0.3362(9) 0.0948(5) 0.6064(15) 0.085(5) Uani 1 1 d D . . . .
H5 H 0.2814 0.0919 0.5838 0.102 Uiso 1 1 calc DR U . . .
C6 C 0.3410(11) 0.0965(8) 0.7580(16) 0.113(7) Uani 1 1 d D . . . .
H6A H 0.3228 0.0628 0.7944 0.169 Uiso 1 1 calc R U . . .
H6B H 0.3935 0.1021 0.7849 0.169 Uiso 1 1 calc R U . . .
H6C H 0.3098 0.1256 0.7915 0.169 Uiso 1 1 calc R U . . .
C7 C 0.3646(12) 0.1476(6) 0.544(2) 0.139(9) Uani 1 1 d D . . . .
H7A H 0.3608 0.1453 0.4469 0.208 Uiso 1 1 calc R U . . .
H7B H 0.3335 0.1771 0.5754 0.208 Uiso 1 1 calc R U . . .
H7C H 0.4173 0.1536 0.5688 0.208 Uiso 1 1 calc R U . . .
C8 C 0.5000 0.2608(7) 0.2500 0.048(5) Uani 1 2 d S T P . .
C9 C 0.4469(8) 0.2338(6) 0.1708(14) 0.061(4) Uani 1 1 d D . . . .
C10 C 0.4495(10) 0.1775(6) 0.1687(18) 0.078(5) Uani 1 1 d . . . . .
H10 H 0.4168 0.1582 0.1119 0.093 Uiso 1 1 calc R U . . .
C11 C 0.5000 0.1506(10) 0.2500 0.100(9) Uani 1 2 d S T P . .
H11 H 0.5000 0.1130 0.2500 0.120 Uiso 1 2 calc R U P . .
C12 C 0.3882(10) 0.2643(6) 0.0852(16) 0.092(5) Uani 1 1 d D . . . .
H12 H 0.4110 0.2993 0.0613 0.110 Uiso 1 1 calc R U . . .
C13 C 0.3171(10) 0.2757(10) 0.169(2) 0.161(11) Uani 1 1 d D . . . .
H13A H 0.3317 0.2933 0.2512 0.241 Uiso 1 1 calc R U . . .
H13B H 0.2830 0.2988 0.1186 0.241 Uiso 1 1 calc R U . . .
H13C H 0.2915 0.2423 0.1889 0.241 Uiso 1 1 calc R U . . .
C14 C 0.3651(13) 0.2365(10) -0.0456(17) 0.183(13) Uani 1 1 d D . . . .
H14A H 0.4103 0.2293 -0.0986 0.275 Uiso 1 1 calc R U . . .
H14B H 0.3395 0.2031 -0.0253 0.275 Uiso 1 1 calc R U . . .
H14C H 0.3310 0.2596 -0.0957 0.275 Uiso 1 1 calc R U . . .
N1 N 0.2548(9) 0.0000 0.5000 0.062(5) Uani 1 2 d S T P . .
H1A H 0.2377 0.0218 0.5651 0.092 Uiso 0.5 1 calc DR U P . .
H1B H 0.2377 -0.0335 0.5145 0.092 Uiso 0.5 1 calc R U P . .
H1C H 0.2377 0.0117 0.4204 0.092 Uiso 0.5 1 calc R U P . .
N2 N 0.5000 0.3201(6) 0.2500 0.068(5) Uani 1 2 d S T P . .
H2A H 0.4616 0.3321 0.3014 0.101 Uiso 0.5 1 calc R U P . .
H2B H 0.4939 0.3321 0.1659 0.101 Uiso 0.5 1 calc R U P . .
H2C H 0.5446 0.3321 0.2827 0.101 Uiso 0.5 1 calc R U P . .
I1 I 0.11831(6) 0.05606(3) 0.81793(8) 0.0553(2) Uani 1 1 d . . . . .
I2 I 0.10739(7) 0.19396(4) 1.07463(11) 0.0788(3) Uani 1 1 d . . . . .
I3 I 0.27636(6) 0.07386(5) 1.16911(12) 0.0828(4) Uani 1 1 d . . . . .
I4 I 0.08062(5) 0.08407(4) 1.42865(8) 0.0564(3) Uani 1 1 d . . . . .
Bi3 Bi 0.11181(3) 0.07891(2) 1.12243(4) 0.04739(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 C2 1.341(16) 2_556 ?
C1 C2 1.341(16) . ?
C1 N1 1.48(2) . ?
C2 C3 1.446(19) . ?
C2 C5 1.529(11) . ?
C3 C4 1.35(2) . ?
C3 H3 0.9300 . ?
C4 C3 1.35(2) 2_556 ?
C4 H4 0.9300 . ?
C5 C6 1.503(12) . ?
C5 C7 1.527(12) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.381(16) 3_655 ?
C8 C9 1.381(16) . ?
C8 N2 1.47(2) . ?
C9 C10 1.391(19) . ?
C9 C12 1.526(11) . ?
C10 C11 1.362(18) . ?
C10 H10 0.9300 . ?
C11 C10 1.362(18) 3_655 ?
C11 H11 0.9300 . ?
C12 C13 1.510(12) . ?
C12 C14 1.519(12) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
I1 Bi3 3.0672(9) . ?
I1 Bi3 3.3879(10) 2_557 ?
I2 Bi3 2.8823(11) . ?
I3 Bi3 2.8969(13) . ?
I4 Bi3 3.0805(9) . ?
I4 Bi3 3.3817(12) 3_557 ?
Bi3 I4 3.3817(12) 3_557 ?
Bi3 I1 3.3879(10) 2_557 ?

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 126.2(18) 2_556 . ?
C2 C1 N1 116.9(9) 2_556 . ?
C2 C1 N1 116.9(9) . . ?
C1 C2 C3 116.0(14) . . ?
C1 C2 C5 126.9(14) . . ?
C3 C2 C5 117.1(15) . . ?
C4 C3 C2 121(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C3 121(3) . 2_556 ?
C3 C4 H4 119.7 . . ?
C3 C4 H4 119.7 2_556 . ?
C6 C5 C7 111.4(14) . . ?
C6 C5 C2 111.4(13) . . ?
C7 C5 C2 114.0(12) . . ?
C6 C5 H5 106.5 . . ?
C7 C5 H5 106.5 . . ?
C2 C5 H5 106.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C9 122.3(18) 3_655 . ?
C9 C8 N2 118.9(9) 3_655 . ?
C9 C8 N2 118.9(9) . . ?
C8 C9 C10 118.0(15) . . ?
C8 C9 C12 121.5(13) . . ?
C10 C9 C12 120.5(14) . . ?
C11 C10 C9 119.9(18) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C10 122(2) . 3_655 ?
C10 C11 H11 119.2 . . ?
C10 C11 H11 119.2 3_655 . ?
C13 C12 C14 109.5(16) . . ?
C13 C12 C9 109.6(14) . . ?
C14 C12 C9 115.2(15) . . ?
C13 C12 H12 107.4 . . ?
C14 C12 H12 107.4 . . ?
C9 C12 H12 107.4 . . ?
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 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C8 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
Bi3 I1 Bi3 90.50(2) . 2_557 ?
Bi3 I4 Bi3 91.44(2) . 3_557 ?
I2 Bi3 I3 95.44(3) . . ?
I2 Bi3 I1 91.22(3) . . ?
I3 Bi3 I1 96.45(3) . . ?
I2 Bi3 I4 96.65(3) . . ?
I3 Bi3 I4 91.05(3) . . ?
I1 Bi3 I4 168.57(3) . . ?
I2 Bi3 I4 84.95(3) . 3_557 ?
I3 Bi3 I4 179.34(3) . 3_557 ?
I1 Bi3 I4 84.06(3) . 3_557 ?
I4 Bi3 I4 88.38(2) . 3_557 ?
I2 Bi3 I1 179.30(3) . 2_557 ?
I3 Bi3 I1 84.09(3) . 2_557 ?
I1 Bi3 I1 89.36(2) . 2_557 ?
I4 Bi3 I1 82.84(2) . 2_557 ?
I4 Bi3 I1 95.51(3) 3_557 2_557 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 0.8(12) 2_556 . . . ?
N1 C1 C2 C3 -179.2(12) . . . . ?
C2 C1 C2 C5 179.9(15) 2_556 . . . ?
N1 C1 C2 C5 -0.1(15) . . . . ?
C1 C2 C3 C4 -2(3) . . . . ?
C5 C2 C3 C4 179.1(15) . . . . ?
C2 C3 C4 C3 0.9(13) . . . 2_556 ?
C1 C2 C5 C6 105.1(16) . . . . ?
C3 C2 C5 C6 -76(2) . . . . ?
C1 C2 C5 C7 -127.8(16) . . . . ?
C3 C2 C5 C7 51(2) . . . . ?
C9 C8 C9 C10 -2.1(10) 3_655 . . . ?
N2 C8 C9 C10 177.9(10) . . . . ?
C9 C8 C9 C12 179.4(15) 3_655 . . . ?
N2 C8 C9 C12 -0.6(15) . . . . ?
C8 C9 C10 C11 4(2) . . . . ?
C12 C9 C10 C11 -177.2(12) . . . . ?
C9 C10 C11 C10 -2.2(11) . . . 3_655 ?
C8 C9 C12 C13 -87.9(17) . . . . ?
C10 C9 C12 C13 93.6(19) . . . . ?
C8 C9 C12 C14 148.1(14) . . . . ?
C10 C9 C12 C14 -30(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A I1 0.89 3.36 4.175(9) 153.8 .
N1 H1B I4 0.89 3.05 3.737(12) 135.1 2_557
N1 H1C I3 0.89 3.00 3.7666(19) 145.7 1_554
N1 H1C I4 0.89 3.26 3.737(12) 115.7 1_554
N2 H2B I2 0.89 3.16 3.7302(17) 124.2 6_556
N2 H2A I1 0.89 3.10 3.746(12) 131.6 8_554
N2 H2A I2 0.89 3.03 3.7302(17) 137.4 8_554
N1 H1A I1 0.89 3.36 4.175(9) 153.8 .
N1 H1B I4 0.89 3.05 3.737(12) 135.1 2_557
N1 H1C I3 0.89 3.00 3.7666(19) 145.7 1_554
N1 H1C I4 0.89 3.26 3.737(12) 115.7 1_554
N2 H2B I2 0.89 3.16 3.7302(17) 124.2 6_556
N2 H2A I1 0.89 3.10 3.746(12) 131.6 8_554
N2 H2A I2 0.89 3.03 3.7302(17) 137.4 8_554

_refine_diff_density_max         1.362
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.114

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1444440'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        iodobismuthate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C12 H20 N), Bi I6, I '
_chemical_formula_sum            'C48 H80 Bi I7 N4'
_chemical_formula_weight         1810.44
_chemical_absolute_configuration rm

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                   18.372(3)
_cell_length_b                   18.431(2)
_cell_length_c                   19.530(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.319(9)
_cell_angle_gamma                90
_cell_volume                     6484.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5411
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      23.08

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      1.853
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_F_000             3400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.082
_shelx_estimated_absorpt_T_min   0.462
_shelx_estimated_absorpt_T_max   0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_T_max  0.581
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            24638
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.823
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             6234
_reflns_number_gt                3843
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0516P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6234
_refine_ls_number_parameters     283
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.0512(4) 0.6833(4) 0.5694(4) 0.0549(19) Uani 1 1 d . . . . .
C2 C 0.0726(5) 0.6143(4) 0.5934(4) 0.067(2) Uani 1 1 d . . . . .
C3 C 0.1326(5) 0.5850(5) 0.5704(5) 0.087(3) Uani 1 1 d . . . . .
H3 H 0.1490 0.5388 0.5851 0.104 Uiso 1 1 calc R U . . .
C4 C 0.1689(6) 0.6227(6) 0.5263(6) 0.100(3) Uani 1 1 d . . . . .
H4 H 0.2083 0.6014 0.5104 0.120 Uiso 1 1 calc R U . . .
C5 C 0.1470(5) 0.6908(6) 0.5060(5) 0.084(3) Uani 1 1 d . . . . .
H5 H 0.1734 0.7164 0.4778 0.101 Uiso 1 1 calc R U . . .
C6 C 0.0863(5) 0.7239(5) 0.5260(4) 0.067(2) Uani 1 1 d . . . . .
C7 C 0.0329(5) 0.5710(4) 0.6415(5) 0.073(2) Uani 1 1 d . . . . .
H7 H 0.0029 0.6047 0.6632 0.087 Uiso 1 1 calc R U . . .
C8 C -0.0187(5) 0.5156(5) 0.6003(5) 0.104(3) Uani 1 1 d . . . . .
H8A H -0.0527 0.5396 0.5637 0.156 Uiso 1 1 calc R U . . .
H8B H -0.0459 0.4913 0.6307 0.156 Uiso 1 1 calc R U . . .
H8C H 0.0099 0.4808 0.5802 0.156 Uiso 1 1 calc R U . . .
C9 C 0.0894(7) 0.5343(6) 0.6999(5) 0.120(4) Uani 1 1 d . . . . .
H9A H 0.1193 0.5010 0.6797 0.180 Uiso 1 1 calc R U . . .
H9B H 0.0634 0.5085 0.7305 0.180 Uiso 1 1 calc R U . . .
H9C H 0.1206 0.5706 0.7260 0.180 Uiso 1 1 calc R U . . .
C10 C 0.0623(6) 0.8012(6) 0.5030(6) 0.100(3) Uani 1 1 d . . . . .
H10 H 0.0122 0.8070 0.5125 0.120 Uiso 1 1 calc DR U . . .
C11 C 0.0549(11) 0.8106(9) 0.4276(7) 0.216(9) Uani 1 1 d . . . . .
H11A H 0.0130 0.8411 0.4103 0.324 Uiso 1 1 calc R U . . .
H11B H 0.0479 0.7641 0.4051 0.324 Uiso 1 1 calc R U . . .
H11C H 0.0991 0.8328 0.4179 0.324 Uiso 1 1 calc R U . . .
C12 C 0.1075(11) 0.8561(7) 0.5449(9) 0.252(13) Uani 1 1 d . . . . .
H12A H 0.1443 0.8737 0.5202 0.379 Uiso 1 1 calc R U . . .
H12B H 0.1316 0.8353 0.5885 0.379 Uiso 1 1 calc R U . . .
H12C H 0.0764 0.8956 0.5535 0.379 Uiso 1 1 calc R U . . .
C13 C 0.2216(4) 0.8931(4) 0.7368(4) 0.060(2) Uani 1 1 d . . . . .
C14 C 0.1876(5) 0.9600(4) 0.7130(5) 0.081(3) Uani 1 1 d . . . . .
C15 C 0.2177(6) 0.9936(5) 0.6612(6) 0.095(3) Uani 1 1 d . . . . .
H15 H 0.1978 1.0376 0.6432 0.114 Uiso 1 1 calc R U . . .
C16 C 0.2753(6) 0.9644(5) 0.6358(6) 0.094(3) Uani 1 1 d . . . . .
H16 H 0.2937 0.9881 0.6007 0.112 Uiso 1 1 calc R U . . .
C17 C 0.3057(5) 0.9005(5) 0.6621(5) 0.083(3) Uani 1 1 d . . . . .
H17 H 0.3459 0.8819 0.6453 0.100 Uiso 1 1 calc R U . . .
C18 C 0.2792(5) 0.8624(4) 0.7123(5) 0.066(2) Uani 1 1 d . . . . .
C19 C 0.1259(6) 0.9928(5) 0.7422(7) 0.114(4) Uani 1 1 d . . . . .
H19 H 0.0960 0.9532 0.7557 0.136 Uiso 1 1 calc R U . . .
C20 C 0.0764(10) 1.0399(10) 0.6932(11) 0.300(16) Uani 1 1 d . . . . .
H20A H 0.0367 1.0565 0.7145 0.450 Uiso 1 1 calc R U . . .
H20B H 0.0564 1.0131 0.6516 0.450 Uiso 1 1 calc R U . . .
H20C H 0.1039 1.0808 0.6814 0.450 Uiso 1 1 calc R U . . .
C21 C 0.1593(9) 1.0364(7) 0.8088(10) 0.214(10) Uani 1 1 d . . . . .
H21A H 0.1205 1.0627 0.8245 0.321 Uiso 1 1 calc R U . . .
H21B H 0.1956 1.0699 0.7985 0.321 Uiso 1 1 calc R U . . .
H21C H 0.1823 1.0036 0.8448 0.321 Uiso 1 1 calc R U . . .
C22 C 0.3092(5) 0.7879(4) 0.7350(5) 0.080(3) Uani 1 1 d . . . . .
H22 H 0.2981 0.7789 0.7813 0.096 Uiso 1 1 calc R U . . .
C23 C 0.2675(7) 0.7311(5) 0.6860(6) 0.118(4) Uani 1 1 d . . . . .
H23A H 0.2152 0.7403 0.6792 0.177 Uiso 1 1 calc R U . . .
H23B H 0.2781 0.6838 0.7061 0.177 Uiso 1 1 calc R U . . .
H23C H 0.2831 0.7333 0.6419 0.177 Uiso 1 1 calc R U . . .
C24 C 0.3936(6) 0.7829(7) 0.7425(7) 0.131(4) Uani 1 1 d . . . . .
H24A H 0.4069 0.7926 0.6982 0.196 Uiso 1 1 calc R U . . .
H24B H 0.4100 0.7351 0.7579 0.196 Uiso 1 1 calc R U . . .
H24C H 0.4170 0.8180 0.7761 0.196 Uiso 1 1 calc R U . . .
N1 N -0.0150(3) 0.7149(3) 0.5904(3) 0.0636(17) Uani 1 1 d . . . . .
H1A H -0.0449 0.7333 0.5530 0.095 Uiso 1 1 calc DR U . . .
H1B H -0.0011 0.7499 0.6216 0.095 Uiso 1 1 calc R U . . .
H1C H -0.0389 0.6805 0.6091 0.095 Uiso 1 1 calc R U . . .
N2 N 0.1904(4) 0.8551(3) 0.7926(3) 0.0684(19) Uani 1 1 d . . . . .
H2A H 0.1998 0.8078 0.7913 0.103 Uiso 1 1 calc R U . . .
H2B H 0.1416 0.8621 0.7854 0.103 Uiso 1 1 calc R U . . .
H2C H 0.2114 0.8728 0.8342 0.103 Uiso 1 1 calc R U . . .
I1 I -0.36406(3) 0.62582(3) 0.46310(3) 0.0761(2) Uani 1 1 d . . . . .
I2 I -0.18931(3) 0.67619(2) 0.64053(3) 0.06217(17) Uani 1 1 d . . . . .
I3 I -0.14181(4) 0.65666(3) 0.43542(3) 0.0810(2) Uani 1 1 d . . . . .
I4 I 0.0000 0.80437(4) 0.7500 0.0680(2) Uani 1 2 d S T P . .
Bi1 Bi -0.2500 0.7500 0.5000 0.05589(14) Uani 1 2 d S . 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 C6 1.382(10) . ?
C1 C2 1.386(11) . ?
C1 N1 1.476(9) . ?
C2 C3 1.379(11) . ?
C2 C7 1.524(11) . ?
C3 C4 1.377(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.353(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(11) . ?
C5 H5 0.9300 . ?
C6 C10 1.532(13) . ?
C7 C8 1.513(12) . ?
C7 C9 1.539(13) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.454(16) . ?
C10 C11 1.463(15) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.366(11) . ?
C13 C14 1.419(11) . ?
C13 N2 1.500(9) . ?
C14 C15 1.390(12) . ?
C14 C19 1.493(13) . ?
C15 C16 1.365(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(11) . ?
C17 H17 0.9300 . ?
C18 C22 1.514(11) . ?
C19 C20 1.467(17) . ?
C19 C21 1.550(19) . ?
C19 H19 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.521(13) . ?
C22 C24 1.531(13) . ?
C22 H22 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
I1 Bi1 3.0913(6) . ?
I2 Bi1 3.0700(6) . ?
I3 Bi1 3.0798(6) . ?
Bi1 I2 3.0701(6) 7_466 ?
Bi1 I3 3.0798(6) 7_466 ?
Bi1 I1 3.0913(6) 7_466 ?

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
C6 C1 C2 124.6(7) . . ?
C6 C1 N1 117.7(7) . . ?
C2 C1 N1 117.6(7) . . ?
C3 C2 C1 116.2(8) . . ?
C3 C2 C7 120.4(8) . . ?
C1 C2 C7 123.4(7) . . ?
C4 C3 C2 121.5(9) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.9(9) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 122.1(9) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 115.5(8) . . ?
C1 C6 C10 122.8(8) . . ?
C5 C6 C10 121.6(8) . . ?
C8 C7 C2 110.5(7) . . ?
C8 C7 C9 111.0(8) . . ?
C2 C7 C9 110.6(8) . . ?
C8 C7 H7 108.2 . . ?
C2 C7 H7 108.2 . . ?
C9 C7 H7 108.2 . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C11 114.4(13) . . ?
C12 C10 C6 112.5(10) . . ?
C11 C10 C6 111.8(10) . . ?
C12 C10 H10 105.8 . . ?
C11 C10 H10 105.8 . . ?
C6 C10 H10 105.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
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 . . ?
C18 C13 C14 124.5(8) . . ?
C18 C13 N2 119.6(7) . . ?
C14 C13 N2 115.9(7) . . ?
C15 C14 C13 114.4(8) . . ?
C15 C14 C19 122.5(8) . . ?
C13 C14 C19 123.1(8) . . ?
C16 C15 C14 122.5(9) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C17 C16 C15 119.6(9) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 122.5(9) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C13 C18 C17 116.6(8) . . ?
C13 C18 C22 122.4(8) . . ?
C17 C18 C22 120.9(8) . . ?
C20 C19 C14 114.3(12) . . ?
C20 C19 C21 109.4(13) . . ?
C14 C19 C21 109.0(10) . . ?
C20 C19 H19 108.0 . . ?
C14 C19 H19 108.0 . . ?
C21 C19 H19 108.0 . . ?
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 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 C23 109.3(8) . . ?
C18 C22 C24 112.8(8) . . ?
C23 C22 C24 113.2(9) . . ?
C18 C22 H22 107.1 . . ?
C23 C22 H22 107.1 . . ?
C24 C22 H22 107.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N2 H2A 109.5 . . ?
C13 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C13 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
I2 Bi1 I2 180.0 . 7_466 ?
I2 Bi1 I3 88.179(18) . . ?
I2 Bi1 I3 91.820(18) 7_466 . ?
I2 Bi1 I3 91.821(18) . 7_466 ?
I2 Bi1 I3 88.180(18) 7_466 7_466 ?
I3 Bi1 I3 180.0 . 7_466 ?
I2 Bi1 I1 90.518(17) . 7_466 ?
I2 Bi1 I1 89.482(17) 7_466 7_466 ?
I3 Bi1 I1 92.67(2) . 7_466 ?
I3 Bi1 I1 87.327(19) 7_466 7_466 ?
I2 Bi1 I1 89.482(17) . . ?
I2 Bi1 I1 90.518(17) 7_466 . ?
I3 Bi1 I1 87.33(2) . . ?
I3 Bi1 I1 92.67(2) 7_466 . ?
I1 Bi1 I1 180.0 7_466 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(13) . . . . ?
N1 C1 C2 C3 177.2(7) . . . . ?
C6 C1 C2 C7 179.7(8) . . . . ?
N1 C1 C2 C7 -1.9(12) . . . . ?
C1 C2 C3 C4 0.0(14) . . . . ?
C7 C2 C3 C4 179.2(9) . . . . ?
C2 C3 C4 C5 1.9(17) . . . . ?
C3 C4 C5 C6 -2.7(16) . . . . ?
C2 C1 C6 C5 0.3(13) . . . . ?
N1 C1 C6 C5 -178.0(7) . . . . ?
C2 C1 C6 C10 -177.7(9) . . . . ?
N1 C1 C6 C10 3.9(12) . . . . ?
C4 C5 C6 C1 1.6(14) . . . . ?
C4 C5 C6 C10 179.7(10) . . . . ?
C3 C2 C7 C8 -78.8(11) . . . . ?
C1 C2 C7 C8 100.3(9) . . . . ?
C3 C2 C7 C9 44.6(11) . . . . ?
C1 C2 C7 C9 -136.3(9) . . . . ?
C1 C6 C10 C12 98.0(14) . . . . ?
C5 C6 C10 C12 -79.9(15) . . . . ?
C1 C6 C10 C11 -131.7(12) . . . . ?
C5 C6 C10 C11 50.4(15) . . . . ?
C18 C13 C14 C15 0.1(13) . . . . ?
N2 C13 C14 C15 -179.8(8) . . . . ?
C18 C13 C14 C19 -178.5(9) . . . . ?
N2 C13 C14 C19 1.5(13) . . . . ?
C13 C14 C15 C16 -0.2(15) . . . . ?
C19 C14 C15 C16 178.4(10) . . . . ?
C14 C15 C16 C17 -0.8(17) . . . . ?
C15 C16 C17 C18 2.0(16) . . . . ?
C14 C13 C18 C17 1.0(13) . . . . ?
N2 C13 C18 C17 -179.1(7) . . . . ?
C14 C13 C18 C22 -174.8(8) . . . . ?
N2 C13 C18 C22 5.1(12) . . . . ?
C16 C17 C18 C13 -2.1(14) . . . . ?
C16 C17 C18 C22 173.8(9) . . . . ?
C15 C14 C19 C20 28.6(18) . . . . ?
C13 C14 C19 C20 -152.8(14) . . . . ?
C15 C14 C19 C21 -94.1(13) . . . . ?
C13 C14 C19 C21 84.4(12) . . . . ?
C13 C18 C22 C23 90.0(11) . . . . ?
C17 C18 C22 C23 -85.7(11) . . . . ?
C13 C18 C22 C24 -143.2(9) . . . . ?
C17 C18 C22 C24 41.2(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A I1 0.89 3.07 3.706(6) 130.0 7_466
N1 H1B I4 0.89 2.70 3.490(6) 148.8 .
N1 H1C I2 0.89 2.95 3.599(6) 131.6 .
N1 H1A I3 0.89 2.97 3.601(6) 129.2 .
N2 H2A I2 0.89 2.79 3.548(6) 143.7 2_556
N2 H2B I4 0.89 2.77 3.558(6) 148.4 .
N2 H2C I1 0.89 3.10 3.677(6) 124.1 8_566
N2 H2C I3 0.89 3.06 3.735(7) 133.8 8_566

_refine_diff_density_max         1.063
_refine_diff_density_min         -1.163
_refine_diff_density_rms         0.166

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_85K
_database_code_depnum_ccdc_archive 'CCDC 1468858'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '2,6 diisopropylanilinium tetraiodobismuthate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi I4, C12 H20 N '
_chemical_formula_sum            'C12 H20 Bi I4 N'
_chemical_formula_weight         894.87

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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.2900(8)
_cell_length_b                   24.7674(11)
_cell_length_c                   9.8852(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4233.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    85(2)
_cell_measurement_reflns_used    3030
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.54

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      2.807
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    2.808
_exptl_crystal_F_000             3152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    14.153
_shelx_estimated_absorpt_T_min   0.225
_shelx_estimated_absorpt_T_max   0.538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1866
_exptl_absorpt_correction_T_max  0.4863
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      85(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            11851
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.512
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4130
_reflns_number_gt                3270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0137P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.416(6)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         4130
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0534
_refine_ls_wR_factor_gt          0.0490
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.966
_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 0.5000 0.7391(7) -0.7500 0.040(4) Uani 1 2 d S T P . .
C2 C 0.4471(7) 0.7659(6) -0.6667(13) 0.048(4) Uani 1 1 d . . . . .
C3 C 0.4505(8) 0.8229(6) -0.6664(15) 0.065(4) Uani 1 1 d . . . . .
H3 H 0.4177 0.8425 -0.6069 0.078 Uiso 1 1 calc R U . . .
C4 C 0.5000 0.8507(9) -0.7500 0.083(8) Uani 1 2 d S T P . .
H4 H 0.5000 0.8891 -0.7500 0.100 Uiso 1 2 calc R U P . .
C5 C 0.3876(9) 0.7360(6) -0.5834(16) 0.075(5) Uani 1 1 d . . . . .
H5 H 0.4122 0.7013 -0.5547 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3177(9) 0.7215(9) -0.662(2) 0.140(10) Uani 1 1 d . . . . .
H6A H 0.2812 0.7023 -0.6036 0.210 Uiso 1 1 calc R U . . .
H6B H 0.2933 0.7544 -0.6967 0.210 Uiso 1 1 calc R U . . .
H6C H 0.3324 0.6983 -0.7381 0.210 Uiso 1 1 calc R U . . .
C7 C 0.3642(11) 0.7661(9) -0.4524(18) 0.139(9) Uani 1 1 d . . . . .
H7A H 0.4108 0.7755 -0.4010 0.209 Uiso 1 1 calc R U . . .
H7B H 0.3360 0.7991 -0.4759 0.209 Uiso 1 1 calc R U . . .
H7C H 0.3310 0.7428 -0.3973 0.209 Uiso 1 1 calc R U . . .
C8 C 0.8409(10) 0.5000 0.0000 0.037(4) Uani 1 2 d S T P . .
C9 C 0.8774(8) 0.5448(5) 0.0488(13) 0.051(3) Uani 1 1 d . . . . .
C10 C 0.9597(8) 0.5440(6) 0.0445(18) 0.086(6) Uani 1 1 d . . . . .
H10 H 0.9879 0.5749 0.0733 0.103 Uiso 1 1 calc R U . . .
C11 C 0.9982(13) 0.5000 0.0000 0.101(11) Uani 1 2 d S T P . .
H11 H 1.0532 0.5000 0.0000 0.122 Uiso 1 2 calc R U P . .
C12 C 0.8384(8) 0.5964(6) 0.1058(16) 0.066(4) Uani 1 1 d . . . . .
H12 H 0.7826 0.5932 0.0808 0.079 Uiso 1 1 calc DR U . . .
C13 C 0.8402(10) 0.5950(8) 0.2555(19) 0.110(7) Uani 1 1 d . . . . .
H13A H 0.8218 0.5598 0.2872 0.166 Uiso 1 1 calc R U . . .
H13B H 0.8933 0.6007 0.2870 0.166 Uiso 1 1 calc R U . . .
H13C H 0.8068 0.6235 0.2915 0.166 Uiso 1 1 calc R U . . .
C14 C 0.8644(9) 0.6463(6) 0.046(2) 0.114(7) Uani 1 1 d D . . . .
H14A H 0.8612 0.6436 -0.0526 0.171 Uiso 1 1 calc R U . . .
H14B H 0.8314 0.6759 0.0774 0.171 Uiso 1 1 calc R U . . .
H14C H 0.9180 0.6532 0.0729 0.171 Uiso 1 1 calc R U . . .
N1 N 0.5000 0.6811(6) -0.7500 0.059(5) Uani 1 2 d S T P . .
H1A H 0.5369 0.6688 -0.8081 0.088 Uiso 0.5 1 calc R U P . .
H1B H 0.5103 0.6688 -0.6651 0.088 Uiso 0.5 1 calc R U P . .
H1C H 0.4528 0.6688 -0.7768 0.088 Uiso 0.5 1 calc R U P . .
N2 N 0.7535(7) 0.5000 0.0000 0.058(5) Uani 1 2 d S T P . .
H2A H 0.7359 0.4682 -0.0346 0.087 Uiso 0.5 1 calc R U P . .
H2B H 0.7359 0.5039 0.0862 0.087 Uiso 0.5 1 calc R U P . .
H2C H 0.7359 0.5278 -0.0516 0.087 Uiso 0.5 1 calc R U P . .
I1 I 0.58087(5) 0.58403(4) -0.07109(8) 0.0477(2) Uani 1 1 d . . . . .
I2 I 0.61882(5) 0.55580(3) -0.68264(8) 0.0470(2) Uani 1 1 d . . . . .
I3 I 0.60848(6) 0.69375(4) -0.42646(11) 0.0675(3) Uani 1 1 d . . . . .
I4 I 0.77797(5) 0.57379(5) -0.32974(11) 0.0706(3) Uani 1 1 d . . . . .
Bi1 Bi 0.61249(3) 0.57874(2) -0.37776(4) 0.03956(13) 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 C2 1.398(14) . ?
C1 C2 1.398(14) 3_653 ?
C1 N1 1.44(2) . ?
C2 C3 1.413(18) . ?
C2 C5 1.512(18) . ?
C3 C4 1.375(17) . ?
C3 H3 0.9500 . ?
C4 C3 1.375(17) 3_653 ?
C4 H4 0.9500 . ?
C5 C6 1.481(19) . ?
C5 C7 1.55(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.364(14) . ?
C8 C9 1.364(14) 2_565 ?
C8 N2 1.51(2) . ?
C9 C10 1.423(17) . ?
C9 C12 1.551(18) . ?
C10 C11 1.351(16) . ?
C10 H10 0.9500 . ?
C11 C10 1.351(16) 2_565 ?
C11 H11 0.9500 . ?
C12 C14 1.441(15) . ?
C12 C13 1.48(2) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
I1 Bi1 3.0832(9) . ?
I1 Bi1 3.3838(9) 3_654 ?
I2 Bi1 3.0689(9) . ?
I2 Bi1 3.3870(10) 2_564 ?
I3 Bi1 2.8898(10) . ?
I4 Bi1 2.9027(10) . ?
Bi1 I1 3.3838(9) 3_654 ?
Bi1 I2 3.3869(10) 2_564 ?

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 123.2(17) . 3_653 ?
C2 C1 N1 118.4(8) . . ?
C2 C1 N1 118.4(8) 3_653 . ?
C1 C2 C3 116.7(13) . . ?
C1 C2 C5 122.1(13) . . ?
C3 C2 C5 121.1(13) . . ?
C4 C3 C2 121.6(16) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C3 120(2) 3_653 . ?
C3 C4 H4 120.0 3_653 . ?
C3 C4 H4 120.0 . . ?
C6 C5 C2 112.8(14) . . ?
C6 C5 C7 110.0(14) . . ?
C2 C5 C7 113.4(14) . . ?
C6 C5 H5 106.7 . . ?
C2 C5 H5 106.7 . . ?
C7 C5 H5 106.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C9 124.9(17) . 2_565 ?
C9 C8 N2 117.6(8) . . ?
C9 C8 N2 117.6(8) 2_565 . ?
C8 C9 C10 116.2(13) . . ?
C8 C9 C12 126.7(12) . . ?
C10 C9 C12 117.1(12) . . ?
C11 C10 C9 120.9(15) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C10 121(2) 2_565 . ?
C10 C11 H11 119.6 2_565 . ?
C10 C11 H11 119.5 . . ?
C14 C12 C13 115.0(15) . . ?
C14 C12 C9 115.0(13) . . ?
C13 C12 C9 109.6(13) . . ?
C14 C12 H12 105.4 . . ?
C13 C12 H12 105.4 . . ?
C9 C12 H12 105.4 . . ?
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 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C8 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
Bi1 I1 Bi1 91.53(2) . 3_654 ?
Bi1 I2 Bi1 90.45(2) . 2_564 ?
I3 Bi1 I4 95.31(3) . . ?
I3 Bi1 I2 91.13(3) . . ?
I4 Bi1 I2 96.76(3) . . ?
I3 Bi1 I1 96.76(3) . . ?
I4 Bi1 I1 90.91(3) . . ?
I2 Bi1 I1 168.46(3) . . ?
I3 Bi1 I1 85.02(3) . 3_654 ?
I4 Bi1 I1 179.16(3) . 3_654 ?
I2 Bi1 I1 84.01(2) . 3_654 ?
I1 Bi1 I1 88.29(2) . 3_654 ?
I3 Bi1 I2 179.26(3) . 2_564 ?
I4 Bi1 I2 84.14(3) . 2_564 ?
I2 Bi1 I2 89.41(2) . 2_564 ?
I1 Bi1 I2 82.77(3) . 2_564 ?
I1 Bi1 I2 95.53(2) 3_654 2_564 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C I3 0.91 3.18 3.7210(16) 120.2 3_653
N1 H1A I2 0.91 3.37 3.780(12) 109.8 .
N1 H1B I3 0.91 2.97 3.7210(16) 140.8 .
N2 H2A I1 0.91 3.15 3.705(10) 120.9 2_565
N2 H2B I4 0.91 3.17 3.7610(17) 124.8 2_565
N2 H2C I1 0.91 3.03 3.705(10) 132.8 .
N2 H2C I4 0.91 3.06 3.7610(17) 134.9 .

_refine_diff_density_max         0.828
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.136

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_296K
_database_code_depnum_ccdc_archive 'CCDC 1468859'
_audit_update_record             
;
2016-03-16 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '2,6 diisopropylanilinium tetraiodobismuthate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi I4, C12 H20 N'
_chemical_formula_sum            'C12 H20 Bi I4 N'
_chemical_formula_weight         894.87

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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

_cell_length_a                   17.3001(6)
_cell_length_b                   24.7219(8)
_cell_length_c                   9.8813(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4226.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2914
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.55

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.813
_exptl_crystal_F_000             3152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    14.177
_shelx_estimated_absorpt_T_min   0.164
_shelx_estimated_absorpt_T_max   0.538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.164
_exptl_absorpt_correction_T_max  0.167
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            9910
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.513
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4133
_reflns_number_gt                3226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.455(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4133
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0585
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 1.0000 0.7393(7) 1.2500 0.041(4) Uani 1 2 d S T P . .
C2 C 0.9475(8) 0.7659(5) 1.3314(14) 0.058(4) Uani 1 1 d . . . . .
C3 C 0.8871(11) 0.7350(7) 1.4163(19) 0.094(6) Uani 1 1 d . . . . .
H3 H 0.9095 0.7000 1.4412 0.113 Uiso 1 1 calc R U . . .
C4 C 0.8154(10) 0.7242(9) 1.333(2) 0.149(10) Uani 1 1 d . . . . .
H4A H 0.7728 0.7165 1.3921 0.223 Uiso 1 1 calc R U . . .
H4B H 0.8244 0.6938 1.2746 0.223 Uiso 1 1 calc R U . . .
H4C H 0.8037 0.7555 1.2792 0.223 Uiso 1 1 calc R U . . .
C5 C 0.8639(13) 0.7639(10) 1.547(2) 0.161(11) Uani 1 1 d . . . . .
H5A H 0.8267 0.7916 1.5265 0.242 Uiso 1 1 calc R U . . .
H5B H 0.9088 0.7801 1.5872 0.242 Uiso 1 1 calc R U . . .
H5C H 0.8417 0.7383 1.6086 0.242 Uiso 1 1 calc R U . . .
C6 C 0.9494(9) 0.8228(6) 1.3303(16) 0.068(4) Uani 1 1 d . . . . .
H6 H 0.9159 0.8426 1.3848 0.082 Uiso 1 1 calc R U . . .
C7 C 1.0000 0.8480(8) 1.2500 0.087(8) Uani 1 2 d S T P . .
H7 H 1.0000 0.8856 1.2500 0.104 Uiso 1 2 calc R U P . .
C8 C 0.6600(10) 0.5000 1.5000 0.046(5) Uani 1 2 d S T P . .
C9 C 0.6231(8) 0.5444(5) 1.4488(14) 0.059(4) Uani 1 1 d . . . . .
C10 C 0.6633(8) 0.5957(5) 1.3941(16) 0.068(4) Uani 1 1 d . . . . .
H10 H 0.7182 0.5928 1.4172 0.081 Uiso 1 1 calc R U . . .
C11 C 0.6578(11) 0.5971(7) 1.2431(19) 0.109(7) Uani 1 1 d . . . . .
H11A H 0.6045 0.5989 1.2167 0.164 Uiso 1 1 calc R U . . .
H11B H 0.6808 0.5650 1.2062 0.164 Uiso 1 1 calc R U . . .
H11C H 0.6846 0.6284 1.2095 0.164 Uiso 1 1 calc R U . . .
C12 C 0.6340(13) 0.6482(6) 1.455(2) 0.141(9) Uani 1 1 d . . . . .
H12A H 0.6529 0.6782 1.4025 0.211 Uiso 1 1 calc R U . . .
H12B H 0.6519 0.6514 1.5463 0.211 Uiso 1 1 calc R U . . .
H12C H 0.5785 0.6484 1.4536 0.211 Uiso 1 1 calc R U . . .
C13 C 0.5423(10) 0.5435(7) 1.451(2) 0.109(7) Uani 1 1 d . . . . .
H13 H 0.5145 0.5730 1.4189 0.131 Uiso 1 1 calc R U . . .
C14 C 0.5046(14) 0.5000 1.5000 0.110(11) Uani 1 2 d S T P . .
H14 H 0.4509 0.5000 1.5000 0.132 Uiso 1 2 calc R U P . .
N1 N 1.0000 0.6803(6) 1.2500 0.065(5) Uani 1 2 d S T P . .
H1A H 0.9637 0.6683 1.3063 0.097 Uiso 0.5 1 calc R U P . .
H1B H 0.9903 0.6683 1.1668 0.097 Uiso 0.5 1 calc R U P . .
H1C H 1.0460 0.6683 1.2769 0.097 Uiso 0.5 1 calc R U P . .
N2 N 0.7456(8) 0.5000 1.5000 0.063(5) Uani 1 2 d S T P . .
H2A H 0.7627 0.5308 1.4644 0.094 Uiso 0.5 1 calc R U P . .
H2B H 0.7627 0.4969 1.5846 0.094 Uiso 0.5 1 calc R U P . .
H2C H 0.7627 0.4723 1.4510 0.094 Uiso 0.5 1 calc R U P . .
I1 I 0.88145(6) 0.55592(3) 1.18220(8) 0.0525(2) Uani 1 1 d . . . . .
I2 I 0.91910(5) 0.58397(4) 0.57148(8) 0.0535(2) Uani 1 1 d . . . . .
I3 I 0.89208(7) 0.69370(4) 0.92574(11) 0.0755(3) Uani 1 1 d . . . . .
I4 I 0.72280(6) 0.57364(5) 0.83067(12) 0.0790(4) Uani 1 1 d . . . . .
Bi1 Bi 0.88778(3) 0.57874(2) 0.87769(4) 0.04465(13) 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 C2 1.381(15) 4_757 ?
C1 C2 1.381(15) . ?
C1 N1 1.46(2) . ?
C2 C6 1.408(18) . ?
C2 C3 1.54(2) . ?
C3 C4 1.51(2) . ?
C3 C5 1.53(2) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.335(16) . ?
C6 H6 0.9300 . ?
C7 C6 1.335(16) 4_757 ?
C7 H7 0.9300 . ?
C8 C9 1.367(15) 3_568 ?
C8 C9 1.367(15) . ?
C8 N2 1.48(2) . ?
C9 C13 1.398(19) . ?
C9 C10 1.545(17) . ?
C10 C11 1.50(2) . ?
C10 C12 1.52(2) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.347(19) . ?
C13 H13 0.9300 . ?
C14 C13 1.347(19) 3_568 ?
C14 H14 0.9300 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
I1 Bi1 3.0634(9) . ?
I1 Bi1 3.3831(9) 3_567 ?
I2 Bi1 3.0766(9) . ?
I2 Bi1 3.3810(10) 4_756 ?
I3 Bi1 2.8823(10) . ?
I4 Bi1 2.8945(11) . ?
Bi1 I2 3.3809(10) 4_756 ?
Bi1 I1 3.3830(9) 3_567 ?

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 123.0(18) 4_757 . ?
C2 C1 N1 118.5(9) 4_757 . ?
C2 C1 N1 118.5(9) . . ?
C1 C2 C6 117.2(14) . . ?
C1 C2 C3 121.7(13) . . ?
C6 C2 C3 121.0(13) . . ?
C4 C3 C5 109.1(16) . . ?
C4 C3 C2 110.3(15) . . ?
C5 C3 C2 113.9(16) . . ?
C4 C3 H3 107.8 . . ?
C5 C3 H3 107.8 . . ?
C2 C3 H3 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 119.1(16) . . ?
C7 C6 H6 120.5 . . ?
C2 C6 H6 120.5 . . ?
C6 C7 C6 124(2) 4_757 . ?
C6 C7 H7 117.8 4_757 . ?
C6 C7 H7 117.8 . . ?
C9 C8 C9 124.2(18) 3_568 . ?
C9 C8 N2 117.9(9) 3_568 . ?
C9 C8 N2 117.9(9) . . ?
C8 C9 C13 116.7(15) . . ?
C8 C9 C10 125.3(13) . . ?
C13 C9 C10 117.9(13) . . ?
C11 C10 C12 110.6(15) . . ?
C11 C10 C9 109.9(13) . . ?
C12 C10 C9 114.5(13) . . ?
C11 C10 H10 107.2 . . ?
C12 C10 H10 107.2 . . ?
C9 C10 H10 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
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 . . ?
C14 C13 C9 120.1(18) . . ?
C14 C13 H13 119.9 . . ?
C9 C13 H13 119.9 . . ?
C13 C14 C13 122(2) 3_568 . ?
C13 C14 H14 118.9 3_568 . ?
C13 C14 H14 118.9 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C8 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
Bi1 I1 Bi1 90.48(2) . 3_567 ?
Bi1 I2 Bi1 91.51(2) . 4_756 ?
I3 Bi1 I4 95.44(3) . . ?
I3 Bi1 I1 91.19(3) . . ?
I4 Bi1 I1 96.57(3) . . ?
I3 Bi1 I2 96.66(3) . . ?
I4 Bi1 I2 91.01(3) . . ?
I1 Bi1 I2 168.53(3) . . ?
I3 Bi1 I2 84.97(3) . 4_756 ?
I4 Bi1 I2 179.24(3) . 4_756 ?
I1 Bi1 I2 84.06(3) . 4_756 ?
I2 Bi1 I2 88.31(2) . 4_756 ?
I3 Bi1 I1 179.30(3) . 3_567 ?
I4 Bi1 I1 84.09(3) . 3_567 ?
I1 Bi1 I1 89.39(2) . 3_567 ?
I2 Bi1 I1 82.82(2) . 3_567 ?
I2 Bi1 I1 95.48(3) 4_756 3_567 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C6 -0.7(9) 4_757 . . . ?
N1 C1 C2 C6 179.3(9) . . . . ?
C2 C1 C2 C3 177.2(15) 4_757 . . . ?
N1 C1 C2 C3 -2.8(15) . . . . ?
C1 C2 C3 C4 -86.8(16) . . . . ?
C6 C2 C3 C4 91.0(19) . . . . ?
C1 C2 C3 C5 150.2(14) . . . . ?
C6 C2 C3 C5 -32(2) . . . . ?
C1 C2 C6 C7 1.3(19) . . . . ?
C3 C2 C6 C7 -176.5(13) . . . . ?
C2 C6 C7 C6 -0.7(10) . . . 4_757 ?
C9 C8 C9 C13 0.6(12) 3_568 . . . ?
N2 C8 C9 C13 -179.4(12) . . . . ?
C9 C8 C9 C10 178.1(15) 3_568 . . . ?
N2 C8 C9 C10 -1.9(15) . . . . ?
C8 C9 C10 C11 106.7(15) . . . . ?
C13 C9 C10 C11 -75.7(19) . . . . ?
C8 C9 C10 C12 -128.0(16) . . . . ?
C13 C9 C10 C12 50(2) . . . . ?
C8 C9 C13 C14 -1(2) . . . . ?
C10 C9 C13 C14 -178.9(15) . . . . ?
C9 C13 C14 C13 0.6(13) . . . 3_568 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B I3 0.89 2.99 3.7232(16) 140.6 .
N1 H1C I1 0.89 3.07 3.756(11) 134.9 4_757
N1 H1C I3 0.89 3.19 3.7232(16) 120.7 4_757
N2 H2A I2 0.89 3.19 3.717(12) 120.3 1_556
N2 H2B I4 0.89 3.16 3.7612(19) 126.7 1_556
N2 H2C I2 0.89 3.05 3.717(12) 133.3 3_567
N2 H2C I4 0.89 3.08 3.7612(19) 134.4 3_567

_refine_diff_density_max         1.151
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.129

_shelxl_version_number           2014-3

