# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1_100K
_database_code_depnum_ccdc_archive 'CCDC 1567568'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_date             2017-04-03T10:58:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         '2(C14 H18 N2), Bi2 I10'
_chemical_formula_sum            'C28 H36 Bi2 I10 N4'
_chemical_formula_weight         2115.57

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   12.5628(6)
_cell_length_b                   12.2070(6)
_cell_length_c                   15.2026(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.0000(10)
_cell_angle_gamma                90
_cell_volume                     2328.19(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      34.14

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    3.018
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1856
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71069   12.566   12.209   15.217   90.010   92.996   90.025
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    14.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0757
_exptl_absorpt_correction_T_max  0.1626

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_number            64771
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         34.378
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_reflns_Friedel_coverage         0
_reflns_number_total             9555
_reflns_number_gt                8236
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9555
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0507
_refine_ls_wR_factor_gt          0.0478
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.522
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.215

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.00421(2) 0.52857(2) 0.15251(2) 0.01093(2) Uani 1 1 d . . . . .
I1 I 0.13375(2) 0.44123(2) 0.30374(2) 0.01816(4) Uani 1 1 d . . . . .
I2 I 0.16416(2) 0.71493(2) 0.13595(2) 0.01752(4) Uani 1 1 d . . . . .
I3 I 0.13594(2) 0.36986(2) 0.01876(2) 0.01642(4) Uani 1 1 d . . . . .
I4 I -0.12312(2) 0.66217(2) 0.26614(2) 0.01875(4) Uani 1 1 d . . . . .
I5 I -0.15275(2) 0.34415(2) 0.17938(2) 0.01703(4) Uani 1 1 d . . . . .
N1 N 0.0352(2) 0.97164(19) -0.10526(17) 0.0144(4) Uani 1 1 d . . . . .
N2 N -0.04100(19) 0.9436(2) -0.28906(17) 0.0161(5) Uani 1 1 d . . . . .
C1 C 0.1011(2) 0.9006(2) -0.06149(19) 0.0150(5) Uani 1 1 d . . . . .
H1A H 0.074792 0.831401 -0.044092 0.018 Uiso 1 1 calc R U . . .
C2 C 0.2062(2) 0.9275(2) -0.0418(2) 0.0172(5) Uani 1 1 d . . . . .
H2A H 0.25164 0.876856 -0.010693 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2463(2) 1.0287(2) -0.0673(2) 0.0168(5) Uani 1 1 d . . . . .
C4 C 0.1761(3) 1.1007(2) -0.1118(2) 0.0184(6) Uani 1 1 d . . . . .
H4A H 0.20066 1.170574 -0.129457 0.022 Uiso 1 1 calc R U . . .
C5 C 0.0716(2) 1.0713(2) -0.1304(2) 0.0175(5) Uani 1 1 d . . . . .
H5A H 0.024582 1.120933 -0.160881 0.021 Uiso 1 1 calc R U . . .
C6 C -0.0758(2) 0.9393(3) -0.1305(2) 0.0173(5) Uani 1 1 d . . . . .
H6A H -0.120905 1.005702 -0.135886 0.021 Uiso 1 1 calc R U . . .
H6B H -0.103632 0.892662 -0.083613 0.021 Uiso 1 1 calc R U . . .
C7 C -0.0827(2) 0.8766(2) -0.2179(2) 0.0179(6) Uani 1 1 d . . . . .
H7A H -0.041059 0.807927 -0.21164 0.022 Uiso 1 1 calc R U . . .
H7B H -0.157878 0.856953 -0.233128 0.022 Uiso 1 1 calc R U . . .
C8 C -0.1007(2) 1.0267(3) -0.3242(2) 0.0211(6) Uani 1 1 d . . . . .
H8A H -0.171089 1.038012 -0.306126 0.025 Uiso 1 1 calc R U . . .
C9 C -0.0595(3) 1.0947(3) -0.3860(2) 0.0234(6) Uani 1 1 d . . . . .
H9A H -0.101802 1.153028 -0.410058 0.028 Uiso 1 1 calc R U . . .
C10 C 0.0431(2) 1.0792(3) -0.4137(2) 0.0196(6) Uani 1 1 d . . . . .
C11 C 0.1024(2) 0.9919(3) -0.3772(2) 0.0206(6) Uani 1 1 d . . . . .
H11A H 0.172483 0.978439 -0.395243 0.025 Uiso 1 1 calc R U . . .
C12 C 0.0593(2) 0.9254(3) -0.3150(2) 0.0174(5) Uani 1 1 d . . . . .
H12A H 0.100061 0.866495 -0.290111 0.021 Uiso 1 1 calc R U . . .
C13 C 0.3602(3) 1.0603(3) -0.0484(2) 0.0246(7) Uani 1 1 d . . . . .
H13A H 0.396894 1.002144 -0.01426 0.037 Uiso 1 1 calc R U . . .
H13B H 0.363456 1.128651 -0.014531 0.037 Uiso 1 1 calc R U . . .
H13C H 0.394975 1.07083 -0.103993 0.037 Uiso 1 1 calc R U . . .
C14 C 0.0902(3) 1.1557(3) -0.4781(2) 0.0264(7) Uani 1 1 d . . . . .
H14A H 0.142289 1.116206 -0.511876 0.04 Uiso 1 1 calc R U . . .
H14B H 0.125696 1.216458 -0.446158 0.04 Uiso 1 1 calc R U . . .
H14C H 0.033508 1.184644 -0.51827 0.04 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 I4 2.9141(2) . ?
Bi1 I1 2.9460(2) . ?
Bi1 I5 3.0344(2) . ?
Bi1 I2 3.0543(2) . ?
Bi1 I3 3.3071(2) 3_565 ?
Bi1 I3 3.3134(2) . ?
N1 C1 1.350(4) . ?
N1 C5 1.362(4) . ?
N1 C6 1.480(4) . ?
N2 C8 1.354(4) . ?
N2 C12 1.358(4) . ?
N2 C7 1.474(4) . ?
C1 C2 1.378(4) . ?
C1 H1A 0.95 . ?
C2 C3 1.397(4) . ?
C2 H2A 0.95 . ?
C3 C4 1.395(4) . ?
C3 C13 1.496(4) . ?
C4 C5 1.376(4) . ?
C4 H4A 0.95 . ?
C5 H5A 0.95 . ?
C6 C7 1.532(4) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.374(5) . ?
C8 H8A 0.95 . ?
C9 C10 1.391(4) . ?
C9 H9A 0.95 . ?
C10 C11 1.398(5) . ?
C10 C14 1.497(4) . ?
C11 C12 1.378(4) . ?
C11 H11A 0.95 . ?
C12 H12A 0.95 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?

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
I4 Bi1 I1 92.169(7) . . ?
I4 Bi1 I5 87.400(7) . . ?
I1 Bi1 I5 87.866(7) . . ?
I4 Bi1 I2 90.914(7) . . ?
I1 Bi1 I2 89.711(7) . . ?
I5 Bi1 I2 176.993(7) . . ?
I4 Bi1 I3 88.324(7) . 3_565 ?
I1 Bi1 I3 178.562(6) . 3_565 ?
I5 Bi1 I3 93.507(6) . 3_565 ?
I2 Bi1 I3 88.930(6) . 3_565 ?
I4 Bi1 I3 176.657(6) . . ?
I1 Bi1 I3 89.660(7) . . ?
I5 Bi1 I3 89.872(6) . . ?
I2 Bi1 I3 91.895(7) . . ?
I3 Bi1 I3 89.914(6) 3_565 . ?
Bi1 I3 Bi1 90.087(6) 3_565 . ?
C1 N1 C5 120.3(3) . . ?
C1 N1 C6 120.1(2) . . ?
C5 N1 C6 119.5(2) . . ?
C8 N2 C12 120.7(3) . . ?
C8 N2 C7 119.6(3) . . ?
C12 N2 C7 119.5(3) . . ?
N1 C1 C2 120.7(3) . . ?
N1 C1 H1A 119.6 . . ?
C2 C1 H1A 119.6 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 C13 120.3(3) . . ?
C2 C3 C13 122.0(3) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
N1 C5 C4 120.5(3) . . ?
N1 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
N1 C6 C7 111.6(2) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108 . . ?
N2 C7 C6 110.7(2) . . ?
N2 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 120.1(3) . . ?
N2 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
C9 C10 C11 117.8(3) . . ?
C9 C10 C14 121.2(3) . . ?
C11 C10 C14 121.0(3) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11A 120 . . ?
C10 C11 H11A 120 . . ?
N2 C12 C11 120.5(3) . . ?
N2 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.2(4) . . . . ?
C6 N1 C1 C2 176.5(3) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C1 C2 C3 C13 -179.0(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C13 C3 C4 C5 179.1(3) . . . . ?
C1 N1 C5 C4 0.3(4) . . . . ?
C6 N1 C5 C4 -176.5(3) . . . . ?
C3 C4 C5 N1 0.2(5) . . . . ?
C1 N1 C6 C7 -84.8(3) . . . . ?
C5 N1 C6 C7 91.9(3) . . . . ?
C8 N2 C7 C6 -75.7(3) . . . . ?
C12 N2 C7 C6 100.5(3) . . . . ?
N1 C6 C7 N2 -58.5(3) . . . . ?
C12 N2 C8 C9 -0.9(5) . . . . ?
C7 N2 C8 C9 175.2(3) . . . . ?
N2 C8 C9 C10 0.3(5) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C8 C9 C10 C14 -177.4(3) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C14 C10 C11 C12 177.0(3) . . . . ?
C8 N2 C12 C11 0.5(4) . . . . ?
C7 N2 C12 C11 -175.6(3) . . . . ?
C10 C11 C12 N2 0.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A I2 0.95 3.23 3.811(3) 121.1 .
C2 H2A I2 0.95 3.22 3.803(3) 121.8 .
C4 H4A I4 0.95 3.04 3.763(3) 134.4 3_575
C5 H5A I2 0.95 3.14 3.945(3) 143.3 3_575
C6 H6A I1 0.99 3.24 4.008(3) 136.1 4_575
C7 H7A I5 0.99 3.08 4.021(3) 159.2 3_565
C7 H7B I2 0.99 3.04 3.944(3) 151.9 4_575
C8 H8A I1 0.95 3.05 3.968(3) 163.4 4_575
C11 H11A I5 0.95 3.25 3.732(3) 113.8 4_675
C12 H12A I5 0.95 3.13 4.026(3) 158.8 3_565

####################################################################### 
# 
# 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 1567571'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_date             2017-02-26T22:24:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C17 H24 N2, Bi I5'
_chemical_formula_sum            'C17 H24 Bi I5 N2'
_chemical_formula_weight         1099.86
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'I 2 2 2'
_symmetry_space_group_name_Hall  'I 2 2'
_symmetry_Int_Tables_number      23
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'

_cell_length_a                   12.2018(4)
_cell_length_b                   13.4499(4)
_cell_length_c                   16.2572(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2668.02(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6484
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      29.96

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    2.738
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1952

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    12.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0127
_exptl_absorpt_correction_T_max  0.0526

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_number            18203
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.254
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.791
_reflns_number_total             3743
_reflns_number_gt                3475
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0400P)²+20.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3743
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.387
_refine_ls_restrained_S_all      1.387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.287(16)
_refine_diff_density_max         2.245
_refine_diff_density_min         -2.263
_refine_diff_density_rms         0.213

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.27348(14) 0.5 0.0315(3) Uani 0.5 2 d S T P . .
Bi1B Bi 0 0.23018(13) 0.5 0.0301(3) Uani 0.5 2 d S T P . .
I1 I 0.07679(7) 0.23116(6) 0.32298(5) 0.03565(19) Uani 1 1 d . . . . .
I2 I 0.23822(7) 0.27259(8) 0.55456(6) 0.0449(2) Uani 1 1 d . . . . .
I3 I 0 0.5105(12) 0.5 0.0357(19) Uani 0.5 2 d S T P . .
I4 I 0 0.0124(8) 0.5 0.0399(16) Uani 0.5 2 d S T P . .
N1 N 0.2259(9) -0.0567(8) 0.2245(8) 0.036(2) Uani 1 1 d . . . . .
C1 C 0.3091(14) -0.0003(16) 0.1941(10) 0.053(4) Uani 1 1 d . . . . .
H1A H 0.323561 -0.001438 0.13671 0.063 Uiso 1 1 calc R U . . .
C2 C 0.3708(14) 0.0565(12) 0.2427(10) 0.050(4) Uani 1 1 d . . . . .
H2A H 0.426828 0.096564 0.219275 0.061 Uiso 1 1 calc R U . . .
C3 C 0.3542(12) 0.0578(10) 0.3269(11) 0.041(3) Uani 1 1 d . . . . .
C4 C 0.2706(13) 0.0016(18) 0.3576(10) 0.057(4) Uani 1 1 d . . . . .
H4A H 0.255488 0.001722 0.414902 0.069 Uiso 1 1 calc R U . . .
C5 C 0.2086(13) -0.0549(14) 0.3056(10) 0.051(4) Uani 1 1 d . . . . .
H5A H 0.151155 -0.094189 0.327856 0.062 Uiso 1 1 calc R U . . .
C6 C 0.1590(12) -0.1203(12) 0.1679(10) 0.046(3) Uani 1 1 d . . . . .
H6A H 0.116167 -0.168655 0.200622 0.055 Uiso 1 1 calc R U . . .
H6B H 0.208429 -0.158045 0.131089 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0811(14) -0.0577(11) 0.1162(10) 0.045(3) Uani 1 1 d . . . . .
H7A H 0.124486 -0.010595 0.082571 0.054 Uiso 1 1 calc R U . . .
H7B H 0.040657 -0.101845 0.078087 0.054 Uiso 1 1 calc R U . . .
C8 C 0 0 0.1669(12) 0.035(4) Uani 1 2 d S T P . .
H8A H 0.03823 0.04612 0.201573 0.042 Uiso 1 1 d R U . . .
C9 C 0.4249(16) 0.1223(12) 0.3826(10) 0.054(4) Uani 1 1 d . . . . .
H9A H 0.480897 0.156014 0.34957 0.081 Uiso 1 1 calc R U . . .
H9B H 0.46052 0.080462 0.424064 0.081 Uiso 1 1 calc R U . . .
H9C H 0.378803 0.17195 0.409941 0.081 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 Bi1B 0.5824(18) . ?
Bi1 I3 2.905(16) 2_565 ?
Bi1 I2 3.0390(8) . ?
Bi1 I2 3.0391(8) 3_556 ?
Bi1 I1 3.0795(9) 3_556 ?
Bi1 I1 3.0796(9) . ?
Bi1 I3 3.188(16) . ?
Bi1 I4 3.511(10) . ?
Bi1 I4 3.845(11) 2 ?
Bi1B I4 2.929(11) . ?
Bi1B I1 3.0265(8) 3_556 ?
Bi1B I1 3.0265(8) . ?
Bi1B I2 3.0921(9) . ?
Bi1B I2 3.0921(9) 3_556 ?
Bi1B I4 3.263(10) 2 ?
Bi1B I3 3.487(16) 2_565 ?
Bi1B I3 3.771(16) . ?
I3 I3 0.28(3) 2_565 ?
I4 I4 0.33(2) 2 ?
N1 C5 1.33(2) . ?
N1 C1 1.36(2) . ?
N1 C6 1.50(2) . ?
C1 C2 1.33(3) . ?
C1 H1A 0.95 . ?
C2 C3 1.38(2) . ?
C2 H2A 0.95 . ?
C3 C4 1.37(2) . ?
C3 C9 1.52(2) . ?
C4 C5 1.36(3) . ?
C4 H4A 0.95 . ?
C5 H5A 0.95 . ?
C6 C7 1.52(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.503(17) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 H8A 0.9597 . ?
C8 H8A 0.9597 2 ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?

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
Bi1B Bi1 I3 180 . 2_565 ?
Bi1B Bi1 I2 89.77(4) . . ?
I3 Bi1 I2 90.23(4) 2_565 . ?
Bi1B Bi1 I2 89.77(4) . 3_556 ?
I3 Bi1 I2 90.23(4) 2_565 3_556 ?
I2 Bi1 I2 179.55(8) . 3_556 ?
Bi1B Bi1 I1 79.35(4) . 3_556 ?
I3 Bi1 I1 100.65(4) 2_565 3_556 ?
I2 Bi1 I1 91.00(2) . 3_556 ?
I2 Bi1 I1 88.91(2) 3_556 3_556 ?
Bi1B Bi1 I1 79.35(4) . . ?
I3 Bi1 I1 100.65(4) 2_565 . ?
I2 Bi1 I1 88.91(2) . . ?
I2 Bi1 I1 91.00(2) 3_556 . ?
I1 Bi1 I1 158.69(8) 3_556 . ?
Bi1B Bi1 I3 180 . . ?
I3 Bi1 I3 0.0000(10) 2_565 . ?
I2 Bi1 I3 90.23(4) . . ?
I2 Bi1 I3 90.23(4) 3_556 . ?
I1 Bi1 I3 100.65(4) 3_556 . ?
I1 Bi1 I3 100.65(4) . . ?
Bi1B Bi1 I4 0.000(3) . . ?
I3 Bi1 I4 180 2_565 . ?
I2 Bi1 I4 89.77(4) . . ?
I2 Bi1 I4 89.77(4) 3_556 . ?
I1 Bi1 I4 79.35(4) 3_556 . ?
I1 Bi1 I4 79.35(4) . . ?
I3 Bi1 I4 180 . . ?
Bi1B Bi1 I4 0.000(3) . 2 ?
I3 Bi1 I4 180 2_565 2 ?
I2 Bi1 I4 89.77(4) . 2 ?
I2 Bi1 I4 89.77(4) 3_556 2 ?
I1 Bi1 I4 79.35(4) 3_556 2 ?
I1 Bi1 I4 79.35(4) . 2 ?
I3 Bi1 I4 180 . 2 ?
I4 Bi1 I4 0 . 2 ?
Bi1 Bi1B I4 180 . . ?
Bi1 Bi1B I1 89.75(4) . 3_556 ?
I4 Bi1B I1 90.25(4) . 3_556 ?
Bi1 Bi1B I1 89.75(4) . . ?
I4 Bi1B I1 90.25(4) . . ?
I1 Bi1B I1 179.50(8) 3_556 . ?
Bi1 Bi1B I2 79.37(4) . . ?
I4 Bi1B I2 100.63(4) . . ?
I1 Bi1B I2 91.00(2) 3_556 . ?
I1 Bi1B I2 88.91(2) . . ?
Bi1 Bi1B I2 79.37(4) . 3_556 ?
I4 Bi1B I2 100.63(4) . 3_556 ?
I1 Bi1B I2 88.91(2) 3_556 3_556 ?
I1 Bi1B I2 91.00(2) . 3_556 ?
I2 Bi1B I2 158.74(8) . 3_556 ?
Bi1 Bi1B I4 180 . 2 ?
I4 Bi1B I4 0 . 2 ?
I1 Bi1B I4 90.25(4) 3_556 2 ?
I1 Bi1B I4 90.25(4) . 2 ?
I2 Bi1B I4 100.63(4) . 2 ?
I2 Bi1B I4 100.63(4) 3_556 2 ?
Bi1 Bi1B I3 0.000(4) . 2_565 ?
I4 Bi1B I3 180 . 2_565 ?
I1 Bi1B I3 89.75(4) 3_556 2_565 ?
I1 Bi1B I3 89.75(4) . 2_565 ?
I2 Bi1B I3 79.37(4) . 2_565 ?
I2 Bi1B I3 79.37(4) 3_556 2_565 ?
I4 Bi1B I3 180 2 2_565 ?
Bi1 Bi1B I3 0.000(4) . . ?
I4 Bi1B I3 180 . . ?
I1 Bi1B I3 89.75(4) 3_556 . ?
I1 Bi1B I3 89.75(4) . . ?
I2 Bi1B I3 79.37(4) . . ?
I2 Bi1B I3 79.37(4) 3_556 . ?
I4 Bi1B I3 180 2 . ?
I3 Bi1B I3 0.0000(10) 2_565 . ?
Bi1B I1 Bi1 10.90(3) . . ?
Bi1 I2 Bi1B 10.86(3) . . ?
I3 I3 Bi1 180.000(12) 2_565 2_565 ?
I3 I3 Bi1 0.000(12) 2_565 . ?
Bi1 I3 Bi1 180 2_565 . ?
I3 I3 Bi1B 180.000(12) 2_565 2_565 ?
Bi1 I3 Bi1B 0 2_565 2_565 ?
Bi1 I3 Bi1B 180 . 2_565 ?
I3 I3 Bi1B 0.000(12) 2_565 . ?
Bi1 I3 Bi1B 180 2_565 . ?
Bi1 I3 Bi1B 0 . . ?
Bi1B I3 Bi1B 180 2_565 . ?
I4 I4 Bi1B 180 2 . ?
I4 I4 Bi1B 0.000(4) 2 2 ?
Bi1B I4 Bi1B 180 . 2 ?
I4 I4 Bi1 180 2 . ?
Bi1B I4 Bi1 0 . . ?
Bi1B I4 Bi1 180 2 . ?
I4 I4 Bi1 0.000(4) 2 2 ?
Bi1B I4 Bi1 180 . 2 ?
Bi1B I4 Bi1 0 2 2 ?
Bi1 I4 Bi1 180 . 2 ?
C5 N1 C1 117.8(15) . . ?
C5 N1 C6 122.1(13) . . ?
C1 N1 C6 120.1(13) . . ?
C2 C1 N1 121.7(14) . . ?
C2 C1 H1A 119.1 . . ?
N1 C1 H1A 119.1 . . ?
C1 C2 C3 120.7(15) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 117.6(16) . . ?
C4 C3 C9 121.5(16) . . ?
C2 C3 C9 120.9(15) . . ?
C5 C4 C3 119.8(15) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C5 C4 122.3(14) . . ?
N1 C5 H5A 118.9 . . ?
C4 C5 H5A 118.9 . . ?
N1 C6 C7 111.4(13) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108 . . ?
C8 C7 C6 113.2(13) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C7 113.5(18) . 2 ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8A 108 2 . ?
C7 C8 H8A 108.0(7) . 2 ?
C7 C8 H8A 109.6(7) 2 2 ?
H8A C8 H8A 107.9 . 2 ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
I2 Bi1 Bi1B I1 91.06(2) . . . 3_556 ?
I2 Bi1 Bi1B I1 -88.94(2) 3_556 . . 3_556 ?
I1 Bi1 Bi1B I1 179.999 . . . 3_556 ?
I4 Bi1 Bi1B I1 0E1(7) . . . 3_556 ?
I4 Bi1 Bi1B I1 0E1(7) 2 . . 3_556 ?
I2 Bi1 Bi1B I1 -88.94(2) . . . . ?
I2 Bi1 Bi1B I1 91.06(2) 3_556 . . . ?
I1 Bi1 Bi1B I1 180.001 3_556 . . . ?
I4 Bi1 Bi1B I1 0E1(10) . . . . ?
I4 Bi1 Bi1B I1 0E1(10) 2 . . . ?
I2 Bi1 Bi1B I2 180 3_556 . . . ?
I1 Bi1 Bi1B I2 -91.06(2) 3_556 . . . ?
I1 Bi1 Bi1B I2 88.94(2) . . . . ?
I4 Bi1 Bi1B I2 0E1(10) . . . . ?
I4 Bi1 Bi1B I2 0E1(10) 2 . . . ?
I2 Bi1 Bi1B I2 180.001 . . . 3_556 ?
I1 Bi1 Bi1B I2 88.94(2) 3_556 . . 3_556 ?
I1 Bi1 Bi1B I2 -91.06(2) . . . 3_556 ?
I4 Bi1 Bi1B I2 0(17) . . . 3_556 ?
I4 Bi1 Bi1B I2 0(17) 2 . . 3_556 ?
I2 Bi1 Bi1B I3 0E1(8) . . . 2_565 ?
I2 Bi1 Bi1B I3 0E1(10) 3_556 . . 2_565 ?
I1 Bi1 Bi1B I3 0E1(10) 3_556 . . 2_565 ?
I1 Bi1 Bi1B I3 0E1(10) . . . 2_565 ?
I4 Bi1 Bi1B I3 0E1(10) . . . 2_565 ?
I4 Bi1 Bi1B I3 0E1(10) 2 . . 2_565 ?
I2 Bi1 Bi1B I3 0E1(8) . . . . ?
I2 Bi1 Bi1B I3 0E1(10) 3_556 . . . ?
I1 Bi1 Bi1B I3 0E1(10) 3_556 . . . ?
I1 Bi1 Bi1B I3 0E1(10) . . . . ?
I4 Bi1 Bi1B I3 0E1(10) . . . . ?
I4 Bi1 Bi1B I3 0E1(10) 2 . . . ?
C5 N1 C1 C2 -1(2) . . . . ?
C6 N1 C1 C2 -179.5(16) . . . . ?
N1 C1 C2 C3 2(3) . . . . ?
C1 C2 C3 C4 -2(3) . . . . ?
C1 C2 C3 C9 179.8(16) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C9 C3 C4 C5 179.6(16) . . . . ?
C1 N1 C5 C4 0(2) . . . . ?
C6 N1 C5 C4 178.9(16) . . . . ?
C3 C4 C5 N1 -1(3) . . . . ?
C5 N1 C6 C7 107.9(16) . . . . ?
C1 N1 C6 C7 -73.7(17) . . . . ?
N1 C6 C7 C8 -60.9(16) . . . . ?
C6 C7 C8 C7 -176.9(15) . . . 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
C1 H1A I3 0.95 3.1 3.925(14) 146.4 5_544
C1 H1A I3 0.95 3.1 3.925(14) 146.6 6_554
C2 H2A I1 0.95 3.03 3.951(16) 163.5 8
C5 H5A I2 0.95 3.25 3.725(14) 113.2 4_556

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1567572'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_date             2017-02-19T19:39:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'Bi4 I16, 2(C17 H24 N2)'
_chemical_formula_sum            'C34 H48 Bi4 I16 N4'
_chemical_formula_weight         3379.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   16.8086(9)
_cell_length_b                   12.0003(6)
_cell_length_c                   17.7036(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.294(2)
_cell_angle_gamma                90
_cell_volume                     3409.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6432
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      27.15

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    3.291
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2920

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    17.561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.4793
_exptl_absorpt_correction_T_max  0.7461

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_number            47874
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         30.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             10422
_reflns_number_gt                7943
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10422
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.293
_refine_diff_density_min         -1.752
_refine_diff_density_rms         0.262

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.07815(2) 0.48840(2) 0.13760(2) 0.01722(5) Uani 1 1 d . . . . .
Bi2 Bi -0.21758(2) 0.55405(2) 0.06474(2) 0.02019(6) Uani 1 1 d . . . . .
I3 I -0.05434(2) 0.67066(3) 0.02186(2) 0.02126(9) Uani 1 1 d . . . . .
I4 I -0.07470(2) 0.38016(3) 0.16419(2) 0.02321(9) Uani 1 1 d . . . . .
I5 I 0.23312(3) 0.58630(3) 0.09704(2) 0.02376(9) Uani 1 1 d . . . . .
I6 I 0.17815(2) 0.31700(3) 0.23657(3) 0.02680(10) Uani 1 1 d . . . . .
I7 I 0.10692(3) 0.64778(4) 0.26478(2) 0.02748(10) Uani 1 1 d . . . . .
I8 I -0.34704(3) 0.69600(4) -0.03575(3) 0.03389(11) Uani 1 1 d . . . . .
I9 I -0.19207(3) 0.70389(5) 0.20029(3) 0.04365(14) Uani 1 1 d . . . . .
I10 I -0.33346(3) 0.39849(4) 0.10310(3) 0.03891(12) Uani 1 1 d . . . . .
N1 N 0.0031(3) 0.2331(5) 0.3826(3) 0.0291(13) Uani 1 1 d . . . . .
N2 N 0.1399(3) -0.0281(4) 0.1124(3) 0.0308(14) Uani 1 1 d . . . . .
C1 C -0.0741(4) 0.2751(7) 0.3699(4) 0.0393(19) Uani 1 1 d . . . . .
H1A H -0.12077 0.226367 0.35672 0.047 Uiso 1 1 calc R U . . .
C2 C -0.0860(4) 0.3846(7) 0.3755(4) 0.0392(19) Uani 1 1 d . . . . .
H2A H -0.141048 0.41163 0.367091 0.047 Uiso 1 1 calc R U . . .
C3 C -0.0202(4) 0.4603(6) 0.3934(4) 0.0302(16) Uani 1 1 d . . . . .
C4 C 0.0584(4) 0.4154(6) 0.4062(4) 0.0304(16) Uani 1 1 d . . . . .
H4A H 0.105587 0.463173 0.419354 0.036 Uiso 1 1 calc R U . . .
C5 C 0.0691(4) 0.3029(6) 0.4002(4) 0.0335(16) Uani 1 1 d . . . . .
H5A H 0.123604 0.273673 0.408527 0.04 Uiso 1 1 calc R U . . .
C6 C 0.0147(4) 0.1145(6) 0.3695(4) 0.0335(16) Uani 1 1 d . . . . .
H6A H -0.029812 0.070534 0.381803 0.04 Uiso 1 1 calc R U . . .
H6B H 0.069028 0.089217 0.405006 0.04 Uiso 1 1 calc R U . . .
C7 C 0.0117(5) 0.0959(6) 0.2839(4) 0.0351(17) Uani 1 1 d . . . . .
H7A H 0.0597 0.134772 0.274197 0.042 Uiso 1 1 calc R U . . .
H7B H -0.039691 0.130651 0.249388 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0136(5) -0.0256(6) 0.2597(4) 0.0365(18) Uani 1 1 d . . . . .
H8A H 0.057838 -0.065181 0.300444 0.044 Uiso 1 1 calc R U . . .
H8B H -0.040381 -0.060984 0.257212 0.044 Uiso 1 1 calc R U . . .
C9 C 0.0294(4) -0.0375(5) 0.1805(4) 0.0351(17) Uani 1 1 d . . . . .
H9A H 0.012269 -0.112859 0.158942 0.042 Uiso 1 1 calc R U . . .
H9B H -0.004624 0.017705 0.143008 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1202(4) -0.0199(6) 0.1881(4) 0.042(2) Uani 1 1 d . . . . .
H10A H 0.137022 0.054709 0.211239 0.05 Uiso 1 1 calc R U . . .
H10B H 0.153485 -0.075933 0.225232 0.05 Uiso 1 1 calc R U . . .
C11 C 0.1355(5) -0.1266(6) 0.0769(4) 0.043(2) Uani 1 1 d . . . . .
H11A H 0.119285 -0.190389 0.100489 0.052 Uiso 1 1 calc R U . . .
C12 C 0.1539(5) -0.1377(6) 0.0065(4) 0.0397(19) Uani 1 1 d . . . . .
H12A H 0.14797 -0.208542 -0.018505 0.048 Uiso 1 1 calc R U . . .
C13 C 0.1807(4) -0.0487(6) -0.0284(5) 0.0346(17) Uani 1 1 d . . . . .
C14 C 0.1848(5) 0.0523(6) 0.0108(5) 0.048(2) Uani 1 1 d . . . . .
H14A H 0.202659 0.11693 -0.010587 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1640(5) 0.0606(6) 0.0787(5) 0.047(2) Uani 1 1 d . . . . .
H15A H 0.166624 0.131395 0.103345 0.056 Uiso 1 1 calc R U . . .
C16 C -0.0344(4) 0.5820(6) 0.3967(4) 0.0371(18) Uani 1 1 d . . . . .
H16A H 0.010479 0.615122 0.439426 0.056 Uiso 1 1 calc R U . . .
H16B H -0.087969 0.595261 0.406589 0.056 Uiso 1 1 calc R U . . .
H16C H -0.035117 0.616116 0.346167 0.056 Uiso 1 1 calc R U . . .
C17 C 0.2044(5) -0.0602(7) -0.1016(5) 0.050(2) Uani 1 1 d . . . . .
H17A H 0.208427 0.013866 -0.12356 0.074 Uiso 1 1 calc R U . . .
H17B H 0.162237 -0.104207 -0.140134 0.074 Uiso 1 1 calc R U . . .
H17C H 0.258518 -0.097767 -0.089839 0.074 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 I7 2.8834(5) . ?
Bi1 I6 2.8939(5) . ?
Bi1 I4 3.0379(5) . ?
Bi1 I5 3.1294(5) . ?
Bi1 I3 3.3318(5) 3_565 ?
Bi1 I3 3.3508(5) . ?
Bi2 I8 2.9155(5) . ?
Bi2 I10 2.9200(5) . ?
Bi2 I9 2.9264(5) . ?
Bi2 I5 3.2654(5) 3_565 ?
Bi2 I4 3.2723(5) . ?
Bi2 I3 3.3618(5) . ?
N1 C1 1.347(9) . ?
N1 C5 1.351(8) . ?
N1 C6 1.465(9) . ?
N2 C11 1.331(9) . ?
N2 C15 1.339(9) . ?
N2 C10 1.477(9) . ?
C1 C2 1.337(11) . ?
C1 H1A 0.95 . ?
C2 C3 1.393(10) . ?
C2 H2A 0.95 . ?
C3 C4 1.382(9) . ?
C3 C16 1.484(10) . ?
C4 C5 1.371(9) . ?
C4 H4A 0.95 . ?
C5 H5A 0.95 . ?
C6 C7 1.519(9) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.522(9) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.511(10) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.507(10) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.376(10) . ?
C11 H11A 0.95 . ?
C12 C13 1.375(10) . ?
C12 H12A 0.95 . ?
C13 C14 1.388(10) . ?
C13 C17 1.472(11) . ?
C14 C15 1.353(11) . ?
C14 H14A 0.95 . ?
C15 H15A 0.95 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?

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
I7 Bi1 I6 93.800(14) . . ?
I7 Bi1 I4 96.652(13) . . ?
I6 Bi1 I4 88.169(13) . . ?
I7 Bi1 I5 88.416(13) . . ?
I6 Bi1 I5 91.860(13) . . ?
I4 Bi1 I5 174.920(13) . . ?
I7 Bi1 I3 172.584(14) . 3_565 ?
I6 Bi1 I3 90.439(13) . 3_565 ?
I4 Bi1 I3 89.556(12) . 3_565 ?
I5 Bi1 I3 85.365(12) . 3_565 ?
I7 Bi1 I3 88.352(13) . . ?
I6 Bi1 I3 174.235(13) . . ?
I4 Bi1 I3 86.269(12) . . ?
I5 Bi1 I3 93.546(12) . . ?
I3 Bi1 I3 88.006(11) 3_565 . ?
I8 Bi2 I10 94.990(16) . . ?
I8 Bi2 I9 92.418(15) . . ?
I10 Bi2 I9 98.475(17) . . ?
I8 Bi2 I5 85.158(13) . 3_565 ?
I10 Bi2 I5 89.386(14) . 3_565 ?
I9 Bi2 I5 171.956(16) . 3_565 ?
I8 Bi2 I4 174.979(14) . . ?
I10 Bi2 I4 84.305(14) . . ?
I9 Bi2 I4 92.603(14) . . ?
I5 Bi2 I4 89.861(12) 3_565 . ?
I8 Bi2 I3 97.484(14) . . ?
I10 Bi2 I3 164.640(14) . . ?
I9 Bi2 I3 89.938(14) . . ?
I5 Bi2 I3 82.790(11) 3_565 . ?
I4 Bi2 I3 82.485(11) . . ?
Bi1 I3 Bi1 91.993(11) 3_565 . ?
Bi1 I3 Bi2 93.000(11) 3_565 . ?
Bi1 I3 Bi2 91.656(12) . . ?
Bi1 I4 Bi2 99.390(13) . . ?
Bi1 I5 Bi2 98.779(12) . 3_565 ?
C1 N1 C5 119.5(6) . . ?
C1 N1 C6 120.3(6) . . ?
C5 N1 C6 120.0(6) . . ?
C11 N2 C15 118.5(7) . . ?
C11 N2 C10 119.5(6) . . ?
C15 N2 C10 122.0(6) . . ?
C2 C1 N1 120.8(7) . . ?
C2 C1 H1A 119.6 . . ?
N1 C1 H1A 119.6 . . ?
C1 C2 C3 122.2(7) . . ?
C1 C2 H2A 118.9 . . ?
C3 C2 H2A 118.9 . . ?
C4 C3 C2 116.0(7) . . ?
C4 C3 C16 122.3(6) . . ?
C2 C3 C16 121.7(7) . . ?
C5 C4 C3 120.9(6) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
N1 C5 C4 120.6(6) . . ?
N1 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
N1 C6 C7 109.5(5) . . ?
N1 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C6 C7 C8 115.1(6) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 112.1(6) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 110.9(6) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108 . . ?
N2 C10 C9 113.9(6) . . ?
N2 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C12 121.2(7) . . ?
N2 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C13 C12 C11 121.6(7) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C14 115.4(8) . . ?
C12 C13 C17 122.3(7) . . ?
C14 C13 C17 122.3(7) . . ?
C15 C14 C13 121.4(7) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
N2 C15 C14 122.0(7) . . ?
N2 C15 H15A 119 . . ?
C14 C15 H15A 119 . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.9(10) . . . . ?
C6 N1 C1 C2 -174.7(7) . . . . ?
N1 C1 C2 C3 1.1(11) . . . . ?
C1 C2 C3 C4 -1.0(10) . . . . ?
C1 C2 C3 C16 177.8(7) . . . . ?
C2 C3 C4 C5 0.9(10) . . . . ?
C16 C3 C4 C5 -177.9(6) . . . . ?
C1 N1 C5 C4 0.9(10) . . . . ?
C6 N1 C5 C4 174.6(6) . . . . ?
C3 C4 C5 N1 -0.9(10) . . . . ?
C1 N1 C6 C7 88.3(7) . . . . ?
C5 N1 C6 C7 -85.4(7) . . . . ?
N1 C6 C7 C8 -173.7(6) . . . . ?
C6 C7 C8 C9 -167.5(6) . . . . ?
C7 C8 C9 C10 77.4(7) . . . . ?
C11 N2 C10 C9 -69.4(8) . . . . ?
C15 N2 C10 C9 111.9(8) . . . . ?
C8 C9 C10 N2 -178.8(6) . . . . ?
C15 N2 C11 C12 -1.0(11) . . . . ?
C10 N2 C11 C12 -179.6(7) . . . . ?
N2 C11 C12 C13 2.5(12) . . . . ?
C11 C12 C13 C14 -2.1(11) . . . . ?
C11 C12 C13 C17 177.0(7) . . . . ?
C12 C13 C14 C15 0.3(11) . . . . ?
C17 C13 C14 C15 -178.8(7) . . . . ?
C11 N2 C15 C14 -0.9(11) . . . . ?
C10 N2 C15 C14 177.7(7) . . . . ?
C13 C14 C15 N2 1.2(12) . . . . ?

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
C1 H1A I9 0.95 3.02 3.849(7) 147.1 2_445
C5 H5A I5 0.95 3.32 4.208(7) 157 2_545
C6 H6A I10 0.99 3.16 4.136(7) 169.1 2_445
C7 H7A I6 0.99 3.16 4.119(7) 163.7 .
C7 H7B I4 0.99 3.33 4.051(7) 131.6 .
C10 H10A I6 0.99 3.23 4.187(8) 164.3 .
C10 H10B I6 0.99 3 3.797(7) 138.7 2_545
C11 H11A I3 0.95 3.29 3.899(7) 123.8 1_545
C11 H11A I5 0.95 3.3 3.787(8) 113.7 1_545
C12 H12A I4 0.95 3.24 4.121(7) 154.3 3
C12 H12A I5 0.95 3.25 3.747(7) 114.8 1_545
C14 H14A I8 0.95 3.23 4.005(8) 140.3 3_565
C15 H15A I6 0.95 3.21 4.116(8) 160.5 .

####################################################################### 
# 
# 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_298K
_database_code_depnum_ccdc_archive 'CCDC 1567570'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_date             2017-04-03T10:48:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         '2(C14 H18 N2), Bi2 I10'
_chemical_formula_sum            'C28 H36 Bi2 I10 N4'
_chemical_formula_weight         2115.57

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   12.6544(16)
_cell_length_b                   12.2914(15)
_cell_length_c                   15.3829(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.656(4)
_cell_angle_gamma                90
_cell_volume                     2390.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.48

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    2.94
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1856
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71067   12.640   12.302   15.372   89.993   92.689   89.989
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    13.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0744
_exptl_absorpt_correction_T_max  0.1561

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_number            45437
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.038
_diffrn_reflns_theta_max         30.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             7283
_reflns_number_gt                5830
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7283
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0714
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.809
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.171

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.00427(2) 0.52871(2) 0.15331(2) 0.02904(5) Uani 1 1 d . . . . .
I1 I 0.13308(3) 0.44158(3) 0.30233(2) 0.05104(10) Uani 1 1 d . . . . .
I2 I 0.16371(3) 0.71410(3) 0.13538(3) 0.04958(10) Uani 1 1 d . . . . .
I3 I 0.13442(3) 0.37265(3) 0.01789(2) 0.04533(9) Uani 1 1 d . . . . .
I4 I -0.12452(3) 0.66193(3) 0.26433(3) 0.05221(10) Uani 1 1 d . . . . .
I5 I -0.15129(3) 0.34504(3) 0.18059(3) 0.04749(9) Uani 1 1 d . . . . .
N1 N 0.0338(3) 0.9706(3) -0.1065(3) 0.0398(9) Uani 1 1 d . . . . .
N2 N -0.0404(3) 0.9460(4) -0.2893(3) 0.0433(10) Uani 1 1 d . . . . .
C1 C 0.0998(4) 0.9007(4) -0.0631(3) 0.0409(11) Uani 1 1 d . . . . .
H1A H 0.074655 0.832933 -0.046717 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2025(4) 0.9279(4) -0.0429(3) 0.0450(12) Uani 1 1 d . . . . .
H2A H 0.246628 0.878828 -0.012881 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2421(5) 1.0297(4) -0.0673(3) 0.0456(12) Uani 1 1 d . . . . .
C4 C 0.1721(5) 1.0990(4) -0.1106(4) 0.0500(13) Uani 1 1 d . . . . .
H4A H 0.195234 1.167306 -0.127407 0.06 Uiso 1 1 calc R U . . .
C5 C 0.0703(5) 1.0697(4) -0.1294(4) 0.0471(13) Uani 1 1 d . . . . .
H5A H 0.024842 1.118371 -0.158381 0.056 Uiso 1 1 calc R U . . .
C6 C -0.0747(4) 0.9375(5) -0.1333(4) 0.0462(12) Uani 1 1 d . . . . .
H6A H -0.119072 1.00177 -0.137859 0.055 Uiso 1 1 calc R U . . .
H6B H -0.102166 0.890985 -0.088722 0.055 Uiso 1 1 calc R U . . .
C7 C -0.0811(4) 0.8771(5) -0.2202(4) 0.0486(13) Uani 1 1 d . . . . .
H7A H -0.039963 0.810582 -0.215395 0.058 Uiso 1 1 calc R U . . .
H7B H -0.154059 0.857545 -0.234904 0.058 Uiso 1 1 calc R U . . .
C8 C -0.0995(4) 1.0281(5) -0.3243(4) 0.0525(14) Uani 1 1 d . . . . .
H8A H -0.168193 1.038172 -0.306804 0.063 Uiso 1 1 calc R U . . .
C9 C -0.0607(5) 1.0955(6) -0.3842(4) 0.0611(16) Uani 1 1 d . . . . .
H9A H -0.102525 1.151864 -0.40705 0.073 Uiso 1 1 calc R U . . .
C10 C 0.0403(5) 1.0815(5) -0.4118(4) 0.0545(15) Uani 1 1 d . . . . .
C11 C 0.1008(4) 0.9964(5) -0.3765(4) 0.0542(15) Uani 1 1 d . . . . .
H11A H 0.169328 0.985125 -0.393824 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0588(4) 0.9298(5) -0.3164(4) 0.0487(13) Uani 1 1 d . . . . .
H12A H 0.098887 0.872207 -0.293519 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3543(5) 1.0616(6) -0.0473(5) 0.0689(18) Uani 1 1 d . . . . .
H13A H 0.390547 1.003239 -0.017051 0.103 Uiso 1 1 calc R U . . .
H13B H 0.388186 1.076513 -0.100532 0.103 Uiso 1 1 calc R U . . .
H13C H 0.356246 1.125495 -0.011389 0.103 Uiso 1 1 calc R U . . .
C14 C 0.0854(6) 1.1591(6) -0.4760(4) 0.078(2) Uani 1 1 d . . . . .
H14A H 0.156177 1.137325 -0.487895 0.118 Uiso 1 1 calc R U . . .
H14B H 0.042351 1.158276 -0.529064 0.118 Uiso 1 1 calc R U . . .
H14C H 0.086559 1.231287 -0.452129 0.118 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 I4 2.9176(4) . ?
Bi1 I1 2.9516(5) . ?
Bi1 I5 3.0371(4) . ?
Bi1 I2 3.0645(4) . ?
Bi1 I3 3.3241(4) . ?
Bi1 I3 3.3252(5) 3_565 ?
N1 C1 1.352(6) . ?
N1 C5 1.355(7) . ?
N1 C6 1.472(7) . ?
N2 C8 1.353(7) . ?
N2 C12 1.356(6) . ?
N2 C7 1.471(7) . ?
C1 C2 1.365(7) . ?
C1 H1A 0.93 . ?
C2 C3 1.405(8) . ?
C2 H2A 0.93 . ?
C3 C4 1.378(8) . ?
C3 C13 1.490(8) . ?
C4 C5 1.356(8) . ?
C4 H4A 0.93 . ?
C5 H5A 0.93 . ?
C6 C7 1.528(8) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.349(8) . ?
C8 H8A 0.93 . ?
C9 C10 1.377(8) . ?
C9 H9A 0.93 . ?
C10 C11 1.391(9) . ?
C10 C14 1.505(9) . ?
C11 C12 1.361(8) . ?
C11 H11A 0.93 . ?
C12 H12A 0.93 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?

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
I4 Bi1 I1 93.001(15) . . ?
I4 Bi1 I5 87.311(14) . . ?
I1 Bi1 I5 87.772(14) . . ?
I4 Bi1 I2 91.337(14) . . ?
I1 Bi1 I2 89.855(13) . . ?
I5 Bi1 I2 177.204(12) . . ?
I4 Bi1 I3 175.673(12) . . ?
I1 Bi1 I3 90.318(14) . . ?
I5 Bi1 I3 90.046(13) . . ?
I2 Bi1 I3 91.448(13) . . ?
I4 Bi1 I3 88.297(14) . 3_565 ?
I1 Bi1 I3 178.311(11) . 3_565 ?
I5 Bi1 I3 93.371(13) . 3_565 ?
I2 Bi1 I3 89.034(12) . 3_565 ?
I3 Bi1 I3 88.438(13) . 3_565 ?
Bi1 I3 Bi1 91.563(12) . 3_565 ?
C1 N1 C5 119.3(5) . . ?
C1 N1 C6 120.6(4) . . ?
C5 N1 C6 120.0(4) . . ?
C8 N2 C12 119.4(5) . . ?
C8 N2 C7 120.8(5) . . ?
C12 N2 C7 119.8(5) . . ?
N1 C1 C2 121.1(5) . . ?
N1 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C1 C2 C3 120.4(5) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 116.7(5) . . ?
C4 C3 C13 121.5(5) . . ?
C2 C3 C13 121.8(6) . . ?
C5 C4 C3 121.5(5) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
N1 C5 C4 121.0(5) . . ?
N1 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
N1 C6 C7 113.0(4) . . ?
N1 C6 H6A 109 . . ?
C7 C6 H6A 109 . . ?
N1 C6 H6B 109 . . ?
C7 C6 H6B 109 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 C6 110.2(4) . . ?
N2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 N2 121.2(5) . . ?
C9 C8 H8A 119.4 . . ?
N2 C8 H8A 119.4 . . ?
C8 C9 C10 120.4(6) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C9 C10 C11 118.4(6) . . ?
C9 C10 C14 120.6(6) . . ?
C11 C10 C14 121.0(6) . . ?
C12 C11 C10 119.6(5) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
N2 C12 C11 121.1(6) . . ?
N2 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.8(7) . . . . ?
C6 N1 C1 C2 175.7(5) . . . . ?
N1 C1 C2 C3 -0.2(8) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C1 C2 C3 C13 -179.2(5) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C13 C3 C4 C5 179.5(6) . . . . ?
C1 N1 C5 C4 1.1(8) . . . . ?
C6 N1 C5 C4 -175.4(5) . . . . ?
C3 C4 C5 N1 -0.4(9) . . . . ?
C1 N1 C6 C7 -85.0(6) . . . . ?
C5 N1 C6 C7 91.4(6) . . . . ?
C8 N2 C7 C6 -76.8(6) . . . . ?
C12 N2 C7 C6 101.0(6) . . . . ?
N1 C6 C7 N2 -59.0(6) . . . . ?
C12 N2 C8 C9 -1.5(9) . . . . ?
C7 N2 C8 C9 176.3(6) . . . . ?
N2 C8 C9 C10 0.6(10) . . . . ?
C8 C9 C10 C11 0.1(10) . . . . ?
C8 C9 C10 C14 -177.6(6) . . . . ?
C9 C10 C11 C12 0.1(9) . . . . ?
C14 C10 C11 C12 177.8(6) . . . . ?
C8 N2 C12 C11 1.7(8) . . . . ?
C7 N2 C12 C11 -176.1(5) . . . . ?
C10 C11 C12 N2 -1.0(8) . . . . ?

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
C1 H1A I2 0.93 3.31 3.874(5) 121.1 .
C2 H2A I2 0.93 3.26 3.847(5) 123.1 .
C4 H4A I4 0.93 3.08 3.802(6) 136.1 3_575
C5 H5A I2 0.93 3.18 3.977(5) 144.4 3_575
C6 H6A I1 0.97 3.3 4.065(5) 137 4_575
C7 H7A I5 0.97 3.11 4.038(6) 160.3 3_565
C7 H7B I2 0.97 3.11 3.994(6) 152.8 4_575
C8 H8A I1 0.93 3.1 4.000(6) 163.9 4_575
C11 H11A I5 0.93 3.25 3.763(6) 116.6 4_675
C12 H12A I5 0.93 3.24 4.113(6) 157.7 3_565

####################################################################### 
# 
# 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_150K
_database_code_depnum_ccdc_archive 'CCDC 1567569'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_date             2017-02-26T18:05:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         '2(C14 H18 N2), Bi2 I10'
_chemical_formula_sum            'C28 H36 Bi2 I10 N4'
_chemical_formula_weight         2115.57

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   12.5792(4)
_cell_length_b                   12.2266(4)
_cell_length_c                   15.2453(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.9530(10)
_cell_angle_gamma                90
_cell_volume                     2341.63(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      31.19

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    3
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1856

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    14.12
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.3129
_exptl_absorpt_correction_T_max  0.4942

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_number            46334
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         31.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             7699
_reflns_number_gt                6420
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7699
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0509
_refine_ls_wR_factor_gt          0.0471
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.074
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.197

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.00423(2) 0.52849(2) 0.15274(2) 0.01309(3) Uani 1 1 d . . . . .
I1 I 0.13378(2) 0.44103(2) 0.30331(2) 0.02379(6) Uani 1 1 d . . . . .
I2 I 0.16397(2) 0.71457(2) 0.13573(2) 0.02277(6) Uani 1 1 d . . . . .
I3 I 0.13542(2) 0.37065(2) 0.01848(2) 0.02121(6) Uani 1 1 d . . . . .
I4 I -0.12309(2) 0.66203(2) 0.26589(2) 0.02442(6) Uani 1 1 d . . . . .
I5 I -0.15230(2) 0.34421(2) 0.17974(2) 0.02194(6) Uani 1 1 d . . . . .
N1 N 0.0348(2) 0.9720(2) -0.1053(2) 0.0165(6) Uani 1 1 d . . . . .
N2 N -0.0408(2) 0.9443(3) -0.2888(2) 0.0202(7) Uani 1 1 d . . . . .
C1 C 0.1012(3) 0.9014(3) -0.0618(2) 0.0200(8) Uani 1 1 d . . . . .
H1A H 0.075184 0.832178 -0.044378 0.024 Uiso 1 1 calc R U . . .
C2 C 0.2054(3) 0.9281(3) -0.0424(2) 0.0216(8) Uani 1 1 d . . . . .
H2A H 0.250827 0.877619 -0.011495 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2455(3) 1.0290(3) -0.0678(3) 0.0221(8) Uani 1 1 d . . . . .
C4 C 0.1750(3) 1.1004(3) -0.1113(3) 0.0241(8) Uani 1 1 d . . . . .
H4A H 0.199088 1.170421 -0.128559 0.029 Uiso 1 1 calc R U . . .
C5 C 0.0715(3) 1.0711(3) -0.1297(2) 0.0210(8) Uani 1 1 d . . . . .
H5A H 0.024555 1.120868 -0.159975 0.025 Uiso 1 1 calc R U . . .
C6 C -0.0752(3) 0.9395(3) -0.1310(3) 0.0214(8) Uani 1 1 d . . . . .
H6A H -0.120393 1.005684 -0.136144 0.026 Uiso 1 1 calc R U . . .
H6B H -0.103048 0.892618 -0.084466 0.026 Uiso 1 1 calc R U . . .
C7 C -0.0825(3) 0.8772(3) -0.2185(3) 0.0221(8) Uani 1 1 d . . . . .
H7A H -0.041234 0.808459 -0.212602 0.027 Uiso 1 1 calc R U . . .
H7B H -0.157703 0.858082 -0.233679 0.027 Uiso 1 1 calc R U . . .
C8 C -0.0996(3) 1.0266(3) -0.3246(3) 0.0261(9) Uani 1 1 d . . . . .
H8A H -0.170291 1.03706 -0.307067 0.031 Uiso 1 1 calc R U . . .
C9 C -0.0597(3) 1.0957(4) -0.3858(3) 0.0286(9) Uani 1 1 d . . . . .
H9A H -0.102035 1.153955 -0.409539 0.034 Uiso 1 1 calc R U . . .
C10 C 0.0429(3) 1.0799(3) -0.4129(3) 0.0245(9) Uani 1 1 d . . . . .
C11 C 0.1013(3) 0.9927(3) -0.3770(3) 0.0249(9) Uani 1 1 d . . . . .
H11A H 0.171086 0.97899 -0.395275 0.03 Uiso 1 1 calc R U . . .
C12 C 0.0588(3) 0.9267(3) -0.3155(3) 0.0220(8) Uani 1 1 d . . . . .
H12A H 0.099587 0.867652 -0.291162 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3591(3) 1.0604(4) -0.0479(3) 0.0320(10) Uani 1 1 d . . . . .
H13A H 0.396438 1.000135 -0.017194 0.048 Uiso 1 1 calc R U . . .
H13B H 0.393325 1.075851 -0.102914 0.048 Uiso 1 1 calc R U . . .
H13C H 0.362008 1.125762 -0.010698 0.048 Uiso 1 1 calc R U . . .
C14 C 0.0894(4) 1.1565(4) -0.4778(3) 0.0361(11) Uani 1 1 d . . . . .
H14A H 0.161955 1.133103 -0.489273 0.054 Uiso 1 1 calc R U . . .
H14B H 0.045483 1.155375 -0.532808 0.054 Uiso 1 1 calc R U . . .
H14C H 0.091217 1.230816 -0.453803 0.054 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 I4 2.9140(3) . ?
Bi1 I1 2.9467(3) . ?
Bi1 I5 3.0342(3) . ?
Bi1 I2 3.0553(3) . ?
Bi1 I3 3.3088(3) 3_565 ?
Bi1 I3 3.3144(3) . ?
N1 C1 1.352(4) . ?
N1 C5 1.355(5) . ?
N1 C6 1.473(5) . ?
N2 C8 1.348(5) . ?
N2 C12 1.353(5) . ?
N2 C7 1.468(5) . ?
C1 C2 1.368(5) . ?
C1 H1A 0.95 . ?
C2 C3 1.395(5) . ?
C2 H2A 0.95 . ?
C3 C4 1.388(6) . ?
C3 C13 1.496(5) . ?
C4 C5 1.366(5) . ?
C4 H4A 0.95 . ?
C5 H5A 0.95 . ?
C6 C7 1.534(5) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.373(6) . ?
C8 H8A 0.95 . ?
C9 C10 1.389(6) . ?
C9 H9A 0.95 . ?
C10 C11 1.391(6) . ?
C10 C14 1.503(6) . ?
C11 C12 1.367(6) . ?
C11 H11A 0.95 . ?
C12 H12A 0.95 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?

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
I4 Bi1 I1 92.348(8) . . ?
I4 Bi1 I5 87.448(8) . . ?
I1 Bi1 I5 87.796(8) . . ?
I4 Bi1 I2 90.972(8) . . ?
I1 Bi1 I2 89.808(8) . . ?
I5 Bi1 I2 177.073(9) . . ?
I4 Bi1 I3 88.424(8) . 3_565 ?
I1 Bi1 I3 178.481(8) . 3_565 ?
I5 Bi1 I3 93.547(8) . 3_565 ?
I2 Bi1 I3 88.871(7) . 3_565 ?
I4 Bi1 I3 176.525(8) . . ?
I1 Bi1 I3 89.817(8) . . ?
I5 Bi1 I3 89.921(8) . . ?
I2 Bi1 I3 91.753(8) . . ?
I3 Bi1 I3 89.475(7) 3_565 . ?
Bi1 I3 Bi1 90.524(7) 3_565 . ?
C1 N1 C5 119.7(3) . . ?
C1 N1 C6 120.4(3) . . ?
C5 N1 C6 119.8(3) . . ?
C8 N2 C12 119.6(4) . . ?
C8 N2 C7 120.2(3) . . ?
C12 N2 C7 120.1(3) . . ?
N1 C1 C2 120.9(3) . . ?
N1 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 117.2(4) . . ?
C4 C3 C13 121.1(4) . . ?
C2 C3 C13 121.7(4) . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
N1 C5 C4 120.8(3) . . ?
N1 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
N1 C6 C7 112.3(3) . . ?
N1 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C6 110.5(3) . . ?
N2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 121.4(4) . . ?
N2 C8 H8A 119.3 . . ?
C9 C8 H8A 119.3 . . ?
C8 C9 C10 119.7(4) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C9 C10 C11 118.0(4) . . ?
C9 C10 C14 120.6(4) . . ?
C11 C10 C14 121.4(4) . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
N2 C12 C11 120.8(4) . . ?
N2 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.4(5) . . . . ?
C6 N1 C1 C2 175.8(3) . . . . ?
N1 C1 C2 C3 -0.4(6) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C1 C2 C3 C13 -179.8(4) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C13 C3 C4 C5 179.7(4) . . . . ?
C1 N1 C5 C4 0.4(5) . . . . ?
C6 N1 C5 C4 -175.9(3) . . . . ?
C3 C4 C5 N1 0.5(6) . . . . ?
C1 N1 C6 C7 -84.6(4) . . . . ?
C5 N1 C6 C7 91.6(4) . . . . ?
C8 N2 C7 C6 -76.6(4) . . . . ?
C12 N2 C7 C6 100.6(4) . . . . ?
N1 C6 C7 N2 -58.3(4) . . . . ?
C12 N2 C8 C9 -2.1(6) . . . . ?
C7 N2 C8 C9 175.2(4) . . . . ?
N2 C8 C9 C10 1.0(6) . . . . ?
C8 C9 C10 C11 0.7(6) . . . . ?
C8 C9 C10 C14 -178.2(4) . . . . ?
C9 C10 C11 C12 -1.4(6) . . . . ?
C14 C10 C11 C12 177.5(4) . . . . ?
C8 N2 C12 C11 1.4(6) . . . . ?
C7 N2 C12 C11 -175.9(4) . . . . ?
C10 C11 C12 N2 0.4(6) . . . . ?

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
C1 H1A I2 0.95 3.25 3.829(4) 121.5 .
C2 H2A I2 0.95 3.23 3.823(4) 122 .
C4 H4A I4 0.95 3.05 3.776(4) 134.6 3_575
C5 H5A I2 0.95 3.15 3.952(4) 143.6 3_575
C6 H6A I1 0.99 3.25 4.020(4) 136.2 4_575
C7 H7A I5 0.99 3.09 4.028(4) 159 3_565
C7 H7B I2 0.99 3.05 3.954(4) 151.9 4_575
C8 H8A I1 0.95 3.07 3.985(4) 163 4_575
C11 H11A I5 0.95 3.26 3.749(4) 113.7 4_675
C12 H12A I5 0.95 3.15 4.048(4) 158.4 3_565

