# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1900233'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2016-12-15T09:25:06-00:00
_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(Bi Br6), 3(C5 H8 N2)'
_chemical_formula_sum            'C15 H24 Bi2 Br12 N6'
_chemical_formula_weight         1665.28

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.3678(6)
_cell_length_b                   14.1378(6)
_cell_length_c                   19.1085(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3611.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6214
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      29.39

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

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    3.063
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2968

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

_exptl_absorpt_coefficient_mu    23.028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.1296
_exptl_absorpt_correction_T_max  0.2657
_exptl_special_details           
;
52010 Corrected reflections written to file 
C:\frames\Ilyukhin\12_13_1\work\12_13_1_0m.hkl
Estimated minimum and maximum transmission:  0.1296  0.2657
The ratio of these values is more reliable than their absolute values!
Additional spherical absorption correction applied with mu*r =  1.0000
;

#----------------------------------------------------------------------------#
#                   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  0.075
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_number            48897
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.097
_diffrn_reflns_theta_max         30.561
_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             5522
_reflns_number_gt                3808
_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)+(0.0400P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5522
_refine_ls_number_parameters     175
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.075
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.36
_refine_diff_density_min         -1.373
_refine_diff_density_rms         0.222

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#
_reflns_special_details          
; 
One of the cations is disordered around two-fold (2) axis, its geometry 
is restricted (AFIX 66 + ISOR 0.01 commands), and part of disordered atoms 
is refined isotropically
;
#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.5 0.03242(2) 0.75 0.01288(7) Uani 1 2 d S T P . .
Bi2 Bi 0.5 0.5 0.5 0.01565(7) Uani 1 2 d S . P . .
Br1 Br 0.64731(5) -0.11195(4) 0.74739(3) 0.02449(14) Uani 1 1 d . . . . .
Br2 Br 0.48007(4) 0.02539(4) 0.60064(3) 0.02001(13) Uani 1 1 d . . . . .
Br3 Br 0.65443(5) 0.17606(4) 0.73776(3) 0.02068(13) Uani 1 1 d . . . . .
Br4 Br 0.65828(4) 0.45200(4) 0.40557(3) 0.02454(14) Uani 1 1 d . . . . .
Br5 Br 0.35269(5) 0.43617(5) 0.40441(3) 0.02956(15) Uani 1 1 d . . . . .
Br6 Br 0.50733(5) 0.31935(4) 0.56724(4) 0.02573(14) Uani 1 1 d . . . . .
N1 N 0.7700(4) 0.2733(4) 0.5125(3) 0.0231(11) Uani 1 1 d . . . . .
N2 N 0.6828(4) 0.1516(3) 0.4236(3) 0.0296(13) Uani 1 1 d . . . . .
H2B H 0.654837 0.111433 0.394346 0.036 Uiso 1 1 calc R U . . .
C1 C 0.7909(4) 0.2779(4) 0.4444(3) 0.0238(13) Uani 1 1 d . . . . .
H1A H 0.836484 0.324115 0.427522 0.029 Uiso 1 1 calc R U . . .
C2 C 0.7467(5) 0.2158(4) 0.3987(3) 0.0261(13) Uani 1 1 d . . . . .
H2A H 0.761348 0.218524 0.350113 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6603(5) 0.1467(5) 0.4909(4) 0.0332(16) Uani 1 1 d . . . . .
H3A H 0.614124 0.100844 0.507539 0.04 Uiso 1 1 calc R U . . .
C4 C 0.7039(5) 0.2078(5) 0.5353(4) 0.0337(17) Uani 1 1 d . . . . .
H4A H 0.688064 0.204847 0.583738 0.04 Uiso 1 1 calc R U . . .
C5 C 0.8195(7) 0.3409(6) 0.5599(5) 0.074(3) Uani 1 1 d . . . . .
H5A H 0.797279 0.329443 0.60803 0.11 Uiso 1 1 calc R U . . .
H5B H 0.892178 0.3326 0.557028 0.11 Uiso 1 1 calc R U . . .
H5C H 0.802003 0.405587 0.546149 0.11 Uiso 1 1 calc R U . . .
N3 N 0.5143(8) 0.4344(4) 0.2506(6) 0.020(3) Uani 0.5 1 d DG U P A -1
C6 C 0.4176(7) 0.4704(6) 0.2521(6) 0.030(4) Uani 0.5 1 d DG U P A -1
H6A H 0.36207 0.428553 0.254088 0.035 Uiso 0.5 1 calc R U P A -1
C7 C 0.4021(7) 0.5676(6) 0.2507(8) 0.025(4) Uani 0.5 1 d G U P A -1
H7A H 0.336013 0.592192 0.251774 0.03 Uiso 0.5 1 calc R U P A -1
N4 N 0.4834(8) 0.6288(4) 0.2478(9) 0.024(3) Uani 0.5 1 d G U P A -1
H4B H 0.47359 0.69035 0.246952 0.029 Uiso 0.5 1 calc R U P A -1
C8 C 0.5801(7) 0.5928(5) 0.2463(7) 0.015(3) Uani 0.5 1 d G U P A -1
H8A H 0.635667 0.634661 0.244306 0.019 Uiso 0.5 1 calc R U P A -1
C9 C 0.5956(7) 0.4956(5) 0.2477(6) 0.017(3) Uani 0.5 1 d DG U P A -1
H9A H 0.661727 0.471022 0.24662 0.021 Uiso 0.5 1 calc R U P A -1
C10 C 0.5284(10) 0.3335(6) 0.2521(8) 0.038(4) Uiso 0.5 1 d D . P A -1
H10A H 0.60006 0.319033 0.250724 0.057 Uiso 0.5 1 calc R U P A -1
H10B H 0.499249 0.307711 0.29511 0.057 Uiso 0.5 1 calc R U P A -1
H10C H 0.495394 0.304949 0.211429 0.057 Uiso 0.5 1 calc R U P A -1



#----------------------------------------------------------------------------#
#                   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 Br1 2.8367(6) . ?
Bi1 Br1 2.8367(6) 3_656 ?
Bi1 Br2 2.8682(6) . ?
Bi1 Br2 2.8682(6) 3_656 ?
Bi1 Br3 2.9053(6) . ?
Bi1 Br3 2.9053(6) 3_656 ?
Bi2 Br5 2.8334(6) . ?
Bi2 Br5 2.8334(6) 5_666 ?
Bi2 Br6 2.8607(6) . ?
Bi2 Br6 2.8607(6) 5_666 ?
Bi2 Br4 2.8624(6) . ?
Bi2 Br4 2.8625(6) 5_666 ?
N1 C1 1.332(8) . ?
N1 C4 1.352(9) . ?
N1 C5 1.474(8) . ?
N2 C3 1.323(8) . ?
N2 C2 1.333(8) . ?
N2 H2B 0.88 . ?
C1 C2 1.372(8) . ?
C1 H1A 0.95 . ?
C2 H2A 0.95 . ?
C3 C4 1.344(10) . ?
C3 H3A 0.95 . ?
C4 H4A 0.95 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
N3 C6 1.39 . ?
N3 C9 1.39 . ?
N3 C10 1.440(7) . ?
C6 C7 1.39 . ?
C6 H6A 0.95 . ?
C7 N4 1.39 . ?
C7 H7A 0.95 . ?
N4 C8 1.39 . ?
N4 H4B 0.88 . ?
C8 C9 1.39 . ?
C8 H8A 0.95 . ?
C9 H9A 0.95 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 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
Br1 Bi1 Br1 87.97(3) . 3_656 ?
Br1 Bi1 Br2 91.264(17) . . ?
Br1 Bi1 Br2 85.873(17) 3_656 . ?
Br1 Bi1 Br2 85.873(17) . 3_656 ?
Br1 Bi1 Br2 91.263(17) 3_656 3_656 ?
Br2 Bi1 Br2 176.02(3) . 3_656 ?
Br1 Bi1 Br3 90.47(2) . . ?
Br1 Bi1 Br3 176.092(16) 3_656 . ?
Br2 Bi1 Br3 90.581(16) . . ?
Br2 Bi1 Br3 92.198(17) 3_656 . ?
Br1 Bi1 Br3 176.093(16) . 3_656 ?
Br1 Bi1 Br3 90.473(19) 3_656 3_656 ?
Br2 Bi1 Br3 92.196(17) . 3_656 ?
Br2 Bi1 Br3 90.583(16) 3_656 3_656 ?
Br3 Bi1 Br3 91.31(3) . 3_656 ?
Br5 Bi2 Br5 180 . 5_666 ?
Br5 Bi2 Br6 91.661(19) . . ?
Br5 Bi2 Br6 88.338(19) 5_666 . ?
Br5 Bi2 Br6 88.340(19) . 5_666 ?
Br5 Bi2 Br6 91.661(19) 5_666 5_666 ?
Br6 Bi2 Br6 180 . 5_666 ?
Br5 Bi2 Br4 91.825(19) . . ?
Br5 Bi2 Br4 88.18(2) 5_666 . ?
Br6 Bi2 Br4 92.645(18) . . ?
Br6 Bi2 Br4 87.355(18) 5_666 . ?
Br5 Bi2 Br4 88.18(2) . 5_666 ?
Br5 Bi2 Br4 91.823(19) 5_666 5_666 ?
Br6 Bi2 Br4 87.354(18) . 5_666 ?
Br6 Bi2 Br4 92.646(18) 5_666 5_666 ?
Br4 Bi2 Br4 180 . 5_666 ?
C1 N1 C4 119.0(6) . . ?
C1 N1 C5 118.3(7) . . ?
C4 N1 C5 122.7(7) . . ?
C3 N2 C2 121.8(6) . . ?
C3 N2 H2B 119.1 . . ?
C2 N2 H2B 119.1 . . ?
N1 C1 C2 120.0(6) . . ?
N1 C1 H1A 120 . . ?
C2 C1 H1A 120 . . ?
N2 C2 C1 119.0(6) . . ?
N2 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
N2 C3 C4 118.8(6) . . ?
N2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C3 C4 N1 121.3(6) . . ?
C3 C4 H4A 119.3 . . ?
N1 C4 H4A 119.3 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 N3 C9 120 . . ?
C6 N3 C10 118.9(7) . . ?
C9 N3 C10 121.1(7) . . ?
N3 C6 C7 120 . . ?
N3 C6 H6A 120 . . ?
C7 C6 H6A 120 . . ?
N4 C7 C6 120 . . ?
N4 C7 H7A 120 . . ?
C6 C7 H7A 120 . . ?
C7 N4 C8 120 . . ?
C7 N4 H4B 120 . . ?
C8 N4 H4B 120 . . ?
C9 C8 N4 120 . . ?
C9 C8 H8A 120 . . ?
N4 C8 H8A 120 . . ?
C8 C9 N3 120 . . ?
C8 C9 H9A 120 . . ?
N3 C9 H9A 120 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
N2 H2B Br1 0.88 2.81 3.445(6) 130.3 7
N2 H2B Br2 0.88 2.65 3.349(5) 137.6 5_656
C1 H1A Br2 0.95 2.92 3.856(6) 170.7 4_556
C2 H2A Br1 0.95 2.91 3.505(6) 122.1 7
C2 H2A Br3 0.95 2.85 3.680(6) 147.2 2_654
C3 H3A Br2 0.95 2.74 3.625(6) 155.2 .
C3 H3A Br2 0.95 3.01 3.536(7) 116.6 5_656
C4 H4A Br3 0.95 3 3.950(7) 173.2 .
C7 H7A Br1 0.95 2.54 3.464(9) 164.8 4_456
N4 H4B Br3 0.88 2.57 3.329(7) 145.6 5_666
N4 H4B Br3 0.88 3.07 3.588(9) 119.4 7_565
C8 H8A Br1 0.95 2.92 3.654(9) 135 2_654
C8 H8A Br3 0.95 2.69 3.419(7) 133.9 7_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 1900234'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2018-07-12T16:14:30-00:00
_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         'Bi2 Br10, 2(C6 H10 N2), 2(H2 O)'
_chemical_formula_sum            'C12 H24 Bi2 Br10 N4 O2'
_chemical_formula_weight         1473.41

#----------------------------------------------------------------------------#
#                   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                   11.1553(14)
_cell_length_b                   11.2184(14)
_cell_length_c                   13.2282(16)
_cell_angle_alpha                90
_cell_angle_beta                 109.653(3)
_cell_angle_gamma                90
_cell_volume                     1559.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5662
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      31.51

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    3.139
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1312

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

_exptl_absorpt_coefficient_mu    24.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0106
_exptl_absorpt_correction_T_max  0.0526
_exptl_special_details           
;
   16499 Corrected reflections written to file INEOS_07_10_2_0m.hkl
 Estimated minimum and maximum transmission:  0.0106  0.0526
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  3.0000
 Lambda/2 correction factor = 0.00150
;

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

_diffrn_ambient_temperature      120(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  0.0416
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_number            16066
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         31.71
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.975
_reflns_Friedel_coverage         0
_reflns_number_total             5158
_reflns_number_gt                4302
_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-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   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         5158
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0585
_refine_ls_wR_factor_gt          0.0554
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.807
_refine_diff_density_min         -1.398
_refine_diff_density_rms         0.188

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.44458(2) 0.50888(2) 0.14759(2) 0.01838(4) Uani 1 1 d . . . . .
Br1 Br 0.52838(4) 0.64415(4) 0.32976(3) 0.02529(9) Uani 1 1 d . . . . .
Br2 Br 0.25364(3) 0.67731(4) 0.05018(3) 0.02232(8) Uani 1 1 d . . . . .
Br3 Br 0.64065(4) 0.33997(4) 0.24733(3) 0.02532(9) Uani 1 1 d . . . . .
Br4 Br 0.61323(4) 0.64430(4) 0.05350(3) 0.02556(9) Uani 1 1 d . . . . .
Br5 Br 0.26630(4) 0.38267(4) 0.20679(3) 0.02431(9) Uani 1 1 d . . . . .
O1 O 0.8544(3) 0.6086(3) 0.4072(2) 0.0291(6) Uani 1 1 d . . . . .
H1 H 0.848947 0.67973 0.363993 0.035 Uiso 1 1 d R U . . .
H2 H 0.761585 0.60435 0.395812 0.035 Uiso 1 1 d R U . . .
N1 N 0.5109(3) 0.0516(3) 0.3086(3) 0.0210(6) Uani 1 1 d . . . . .
N2 N 0.4236(3) -0.0496(3) 0.1146(3) 0.0217(6) Uani 1 1 d . . . . .
H2A H 0.396385 -0.082767 0.050565 0.026 Uiso 1 1 calc R U . . .
C1 C 0.4042(4) 0.0939(4) 0.2359(3) 0.0228(8) Uani 1 1 d . . . . .
H1A H 0.360583 0.159301 0.253208 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3576(4) 0.0414(4) 0.1345(3) 0.0214(7) Uani 1 1 d . . . . .
C3 C 0.5292(4) -0.0925(4) 0.1876(3) 0.0258(8) Uani 1 1 d . . . . .
H3A H 0.573012 -0.158208 0.170963 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5734(4) -0.0400(4) 0.2873(3) 0.0225(8) Uani 1 1 d . . . . .
H4A H 0.648146 -0.069125 0.340417 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5583(4) 0.1093(4) 0.4157(3) 0.0264(8) Uani 1 1 d . . . . .
H5A H 0.485867 0.133721 0.437035 0.04 Uiso 1 1 calc R U . . .
H5B H 0.609043 0.179542 0.412333 0.04 Uiso 1 1 calc R U . . .
H5C H 0.6112 0.052787 0.46842 0.04 Uiso 1 1 calc R U . . .
C6 C 0.2388(4) 0.0816(4) 0.0503(3) 0.0288(9) Uani 1 1 d . . . . .
H6A H 0.202044 0.148296 0.077713 0.043 Uiso 1 1 calc R U . . .
H6B H 0.177781 0.015587 0.030856 0.043 Uiso 1 1 calc R U . . .
H6C H 0.25837 0.107372 -0.013225 0.043 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 Br1 2.7328(5) . ?
Bi1 Br5 2.7606(5) . ?
Bi1 Br2 2.8144(5) . ?
Bi1 Br3 2.8591(5) . ?
Bi1 Br4 2.9952(5) . ?
Bi1 Br4 3.0482(5) 3_665 ?
O1 H1 0.9715 . ?
O1 H2 0.9963 . ?
N1 C4 1.324(5) . ?
N1 C1 1.340(5) . ?
N1 C5 1.483(5) . ?
N2 C2 1.336(5) . ?
N2 C3 1.337(5) . ?
N2 H2A 0.88 . ?
C1 C2 1.395(5) . ?
C1 H1A 0.95 . ?
C2 C6 1.486(5) . ?
C3 C4 1.375(6) . ?
C3 H3A 0.95 . ?
C4 H4A 0.95 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 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
Br1 Bi1 Br5 95.744(14) . . ?
Br1 Bi1 Br2 90.728(15) . . ?
Br5 Bi1 Br2 88.149(15) . . ?
Br1 Bi1 Br3 88.820(14) . . ?
Br5 Bi1 Br3 92.376(15) . . ?
Br2 Bi1 Br3 179.339(13) . . ?
Br1 Bi1 Br4 90.481(14) . . ?
Br5 Bi1 Br4 172.359(12) . . ?
Br2 Bi1 Br4 87.344(15) . . ?
Br3 Bi1 Br4 92.177(15) . . ?
Br1 Bi1 Br4 172.661(12) . 3_665 ?
Br5 Bi1 Br4 89.842(14) . 3_665 ?
Br2 Bi1 Br4 94.215(14) . 3_665 ?
Br3 Bi1 Br4 86.189(14) . 3_665 ?
Br4 Bi1 Br4 84.341(14) . 3_665 ?
Bi1 Br4 Bi1 95.658(14) . 3_665 ?
H1 O1 H2 95.4 . . ?
C4 N1 C1 121.7(3) . . ?
C4 N1 C5 119.9(3) . . ?
C1 N1 C5 118.5(3) . . ?
C2 N2 C3 122.8(3) . . ?
C2 N2 H2A 118.6 . . ?
C3 N2 H2A 118.6 . . ?
N1 C1 C2 119.6(4) . . ?
N1 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
N2 C2 C1 117.5(4) . . ?
N2 C2 C6 119.7(4) . . ?
C1 C2 C6 122.8(4) . . ?
N2 C3 C4 118.9(4) . . ?
N2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
N1 C4 C3 119.5(4) . . ?
N1 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 Br3 0.97 2.35 3.316(3) 171.8 2_655 yes
O1 H2 Br1 1 2.49 3.454(3) 162.7 . yes
N2 H2A O1 0.88 1.82 2.671(4) 162.9 4_565 yes
C1 H1A Br5 0.95 2.71 3.551(4) 148.4 . yes
C3 H3A Br3 0.95 3.01 3.570(4) 119.3 2_645 yes
C3 H3A Br4 0.95 2.83 3.723(4) 157.6 1_545 yes
C4 H4A Br2 0.95 2.89 3.716(4) 145.8 4_666 yes
C4 H4A Br3 0.95 3.13 3.631(4) 114.9 2_645 yes

####################################################################### 
# 
# 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 1900235'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2017-03-09T08:51:25-00:00
_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         'Bi Br5, C7 H12 N2, H2 O'
_chemical_formula_sum            'C7 H14 Bi Br5 N2 O'
_chemical_formula_weight         750.73

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1129(7)
_cell_length_b                   22.6442(16)
_cell_length_c                   8.2570(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.174(2)
_cell_angle_gamma                90
_cell_volume                     1627.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3418
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.21

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

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    3.063
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1344

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

_exptl_absorpt_coefficient_mu    23.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0135
_exptl_absorpt_correction_T_max  0.0504
_exptl_special_details           
;
   25039 Corrected reflections written to file 
C:\frames\Ilyukhin\03_08_3\work\03_08_3_0m.hkl
 Estimated minimum and maximum transmission:  0.0135  0.0504
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  3.0000

;

#----------------------------------------------------------------------------#
#                   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  0.0632
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_number            24625
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         30.061
_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             4765
_reflns_number_gt                3699
_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, 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   mixed

#----------------------------------------------------------------------------#
#                   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)+(0.0600P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4765
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.853
_refine_diff_density_min         -1.199
_refine_diff_density_rms         0.232

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.62468(3) 0.15168(2) 0.72808(3) 0.02323(9) Uani 1 1 d . . . . .
Br1 Br 0.61025(10) 0.06571(4) 0.95998(11) 0.03534(18) Uani 1 1 d . . . . .
Br2 Br 0.95013(8) 0.13173(4) 0.81609(9) 0.03026(17) Uani 1 1 d . . . . .
Br3 Br 0.30166(9) 0.15779(4) 0.63560(11) 0.03508(19) Uani 1 1 d . . . . .
Br4 Br 0.58901(9) 0.07007(4) 0.47808(10) 0.03290(18) Uani 1 1 d . . . . .
Br5 Br 0.64734(9) 0.25176(3) 0.49321(9) 0.03267(18) Uani 1 1 d . . . . .
O1 O -0.1552(9) -0.0211(3) 0.3370(11) 0.077(2) Uani 1 1 d . . . . .
H1 H -0.189116 -0.055242 0.341028 0.092 Uiso 1 1 d R U . . .
H2 H -0.216436 0.001718 0.369458 0.092 Uiso 1 1 d R U . . .
N1 N 0.2372(7) 0.1287(3) 0.1781(8) 0.0296(13) Uani 1 1 d . . . . .
N2 N 0.0367(8) 0.0564(3) 0.2583(8) 0.0327(14) Uani 1 1 d . . . . .
H2A H -0.028032 0.032416 0.286001 0.039 Uiso 1 1 calc R U . . .
C1 C 0.1208(8) 0.1525(3) 0.2290(9) 0.0274(15) Uani 1 1 d . . . . .
C2 C 0.0154(8) 0.1147(4) 0.2705(9) 0.0279(15) Uani 1 1 d . . . . .
C3 C 0.1488(8) 0.0321(4) 0.2072(10) 0.0341(18) Uani 1 1 d . . . . .
H3A H 0.15619 -0.009515 0.197581 0.041 Uiso 1 1 calc R U . . .
C4 C 0.2533(9) 0.0690(4) 0.1690(9) 0.0320(17) Uani 1 1 d . . . . .
H4A H 0.336605 0.053047 0.136177 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3486(10) 0.1671(4) 0.1331(11) 0.0378(19) Uani 1 1 d . . . . .
H5A H 0.393691 0.194333 0.226967 0.057 Uiso 1 1 calc R U . . .
H5B H 0.296626 0.189794 0.03122 0.057 Uiso 1 1 calc R U . . .
H5C H 0.429862 0.14297 0.111208 0.057 Uiso 1 1 calc R U . . .
C6 C 0.0982(9) 0.2175(4) 0.2267(11) 0.0359(18) Uani 1 1 d . . . . .
H6A H 0.115903 0.234074 0.124449 0.054 Uiso 1 1 calc R U . . .
H6B H 0.170781 0.235 0.327291 0.054 Uiso 1 1 calc R U . . .
H6C H -0.007111 0.226294 0.226784 0.054 Uiso 1 1 calc R U . . .
C7 C -0.1092(9) 0.1362(4) 0.3289(11) 0.040(2) Uani 1 1 d . . . . .
H7A H -0.181629 0.104026 0.326579 0.06 Uiso 1 1 calc R U . . .
H7B H -0.162328 0.168263 0.254663 0.06 Uiso 1 1 calc R U . . .
H7C H -0.06834 0.151071 0.44504 0.06 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 Br4 2.7177(8) . ?
Bi1 Br1 2.7608(8) . ?
Bi1 Br3 2.8178(8) . ?
Bi1 Br2 2.8731(8) . ?
Bi1 Br5 3.0293(8) . ?
Bi1 Br5 3.0576(8) 4_566 ?
O1 H1 0.836 . ?
O1 H2 0.8598 . ?
N1 C1 1.362(9) . ?
N1 C4 1.364(10) . ?
N1 C5 1.466(10) . ?
N2 C3 1.334(10) . ?
N2 C2 1.343(10) . ?
N2 H2A 0.88 . ?
C1 C2 1.402(10) . ?
C1 C6 1.485(11) . ?
C2 C7 1.444(11) . ?
C3 C4 1.371(11) . ?
C3 H3A 0.95 . ?
C4 H4A 0.95 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 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
Br4 Bi1 Br1 91.59(3) . . ?
Br4 Bi1 Br3 86.93(2) . . ?
Br1 Bi1 Br3 87.86(3) . . ?
Br4 Bi1 Br2 88.18(2) . . ?
Br1 Bi1 Br2 88.32(2) . . ?
Br3 Bi1 Br2 173.71(3) . . ?
Br4 Bi1 Br5 92.17(2) . . ?
Br1 Bi1 Br5 176.17(3) . . ?
Br3 Bi1 Br5 93.04(2) . . ?
Br2 Bi1 Br5 91.10(2) . . ?
Br4 Bi1 Br5 176.15(2) . 4_566 ?
Br1 Bi1 Br5 90.84(2) . 4_566 ?
Br3 Bi1 Br5 90.18(2) . 4_566 ?
Br2 Bi1 Br5 94.87(2) . 4_566 ?
Br5 Bi1 Br5 85.435(9) . 4_566 ?
Bi1 Br5 Bi1 172.06(3) . 4_565 ?
H1 O1 H2 105.2 . . ?
C1 N1 C4 121.0(7) . . ?
C1 N1 C5 120.3(7) . . ?
C4 N1 C5 118.7(7) . . ?
C3 N2 C2 124.8(7) . . ?
C3 N2 H2A 117.6 . . ?
C2 N2 H2A 117.6 . . ?
N1 C1 C2 119.0(7) . . ?
N1 C1 C6 120.3(7) . . ?
C2 C1 C6 120.4(7) . . ?
N2 C2 C1 117.2(7) . . ?
N2 C2 C7 120.2(7) . . ?
C1 C2 C7 122.5(8) . . ?
N2 C3 C4 118.1(8) . . ?
N2 C3 H3A 121 . . ?
C4 C3 H3A 121 . . ?
N1 C4 C3 119.9(7) . . ?
N1 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
O1 H1 Br3 0.84 2.57 3.404(7) 176.8 3_556
O1 H2 Br4 0.86 2.7 3.558(9) 177.8 1_455
N2 H2A O1 0.88 1.81 2.690(10) 175.9 .
C3 H3A Br1 0.95 3.08 3.664(8) 121.3 3_656
C3 H3A Br2 0.95 2.92 3.810(9) 155.8 3_656
C4 H4A Br1 0.95 2.89 3.574(8) 130.3 3_656

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1900240'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2016-12-18T18:33:28-00:00
_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 Br16, 4(C5 H7 N2)'
_chemical_formula_sum            'C20 H28 Bi4 Br16 N8'
_chemical_formula_weight         2494.98

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7987(3)
_cell_length_b                   10.7742(2)
_cell_length_c                   19.2670(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.6870(10)
_cell_angle_gamma                90
_cell_volume                     2531.25(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8328
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      28.25

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    3.273
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2192

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

_exptl_absorpt_coefficient_mu    26.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0165
_exptl_absorpt_correction_T_max  0.0526
_exptl_special_details           
;
   60358 Corrected reflections written to file 
C:\frames\Ilyukhin\12_16_3\work\12_16_3_0m.hkl
 Estimated minimum and maximum transmission:  0.0165  0.0526
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  3.0000

;

#----------------------------------------------------------------------------#
#                   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  0.0647
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_number            58576
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.192
_diffrn_reflns_theta_max         31.545
_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             8437
_reflns_number_gt                6192
_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)+(0.0500P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8437
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.27
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.223

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.14759(2) 0.40025(2) 0.08244(2) 0.02664(6) Uani 1 1 d . . . . .
Bi2 Bi -0.21042(2) 0.28955(2) 0.05966(2) 0.02742(6) Uani 1 1 d . . . . .
Br1 Br -0.07206(5) 0.53711(6) 0.08335(3) 0.03024(13) Uani 1 1 d . . . . .
Br2 Br 0.01075(5) 0.18215(6) 0.05078(4) 0.03113(13) Uani 1 1 d . . . . .
Br3 Br 0.26280(6) 0.63257(6) 0.10517(4) 0.03639(15) Uani 1 1 d . . . . .
Br4 Br 0.18872(6) 0.36545(7) 0.22608(3) 0.03418(14) Uani 1 1 d . . . . .
Br5 Br 0.32205(6) 0.26789(7) 0.07081(4) 0.03911(16) Uani 1 1 d . . . . .
Br6 Br -0.39482(6) 0.39496(7) 0.07047(4) 0.04234(17) Uani 1 1 d . . . . .
Br7 Br -0.31017(6) 0.07542(6) 0.00068(4) 0.03727(16) Uani 1 1 d . . . . .
Br8 Br -0.16008(6) 0.20226(6) 0.19823(4) 0.03762(16) Uani 1 1 d . . . . .
N1 N 0.4485(5) 0.3237(5) 0.3423(3) 0.0323(12) Uani 1 1 d . . . . .
N2 N 0.4734(5) 0.5421(6) 0.2769(4) 0.0411(14) Uani 1 1 d . . . . .
N3 N 0.0534(5) -0.0658(5) 0.1670(3) 0.0322(12) Uani 1 1 d . . . . .
N4 N 0.2573(5) 0.0332(7) 0.2348(3) 0.0447(15) Uani 1 1 d . . . . .
C1 C 0.4774(6) 0.3205(7) 0.2820(4) 0.0352(14) Uani 1 1 d . . . . .
H1A H 0.489706 0.243765 0.261496 0.042 Uiso 1 1 calc R U . . .
C2 C 0.4895(6) 0.4334(7) 0.2494(4) 0.0415(17) Uani 1 1 d . . . . .
H2A H 0.510039 0.432257 0.205979 0.05 Uiso 1 1 calc R U . . .
C3 C 0.4427(6) 0.5382(7) 0.3371(4) 0.0423(17) Uani 1 1 d . . . . .
H3A H 0.429532 0.614427 0.35781 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4292(6) 0.4288(7) 0.3709(4) 0.0378(15) Uani 1 1 d . . . . .
H4A H 0.406596 0.429513 0.413524 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4344(7) 0.2058(7) 0.3774(5) 0.0485(19) Uani 1 1 d . . . . .
H5A H 0.404414 0.222643 0.41754 0.073 Uiso 1 1 calc R U . . .
H5B H 0.505592 0.164361 0.396287 0.073 Uiso 1 1 calc R U . . .
H5C H 0.383826 0.151932 0.341511 0.073 Uiso 1 1 calc R U . . .
C6 C 0.1343(6) -0.0775(8) 0.1363(4) 0.0442(18) Uani 1 1 d . . . . .
H6A H 0.121874 -0.1204 0.091453 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2346(7) -0.0266(9) 0.1706(4) 0.054(2) Uani 1 1 d . . . . .
H7A H 0.290794 -0.033744 0.147991 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1759(6) 0.0433(7) 0.2638(4) 0.0392(16) Uani 1 1 d . . . . .
H8A H 0.188494 0.085802 0.308755 0.047 Uiso 1 1 calc R U . . .
C9 C 0.0742(6) -0.0060(7) 0.2306(4) 0.0358(15) Uani 1 1 d . . . . .
H9A H 0.017894 0.002515 0.252989 0.043 Uiso 1 1 calc R U . . .
C10 C -0.0575(7) -0.1161(7) 0.1306(4) 0.0438(18) Uani 1 1 d . . . . .
H10A H -0.066282 -0.129431 0.078822 0.066 Uiso 1 1 calc R U . . .
H10B H -0.112901 -0.057022 0.135663 0.066 Uiso 1 1 calc R U . . .
H10C H -0.066562 -0.195209 0.153237 0.066 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 Br4 2.6816(7) . ?
Bi1 Br5 2.7154(7) . ?
Bi1 Br3 2.8703(7) . ?
Bi1 Br2 2.8831(7) . ?
Bi1 Br1 3.1171(7) 3_565 ?
Bi1 Br1 3.1792(7) . ?
Bi2 Br6 2.6837(7) . ?
Bi2 Br7 2.7133(7) . ?
Bi2 Br8 2.7171(7) . ?
Bi2 Br2 3.1106(7) . ?
Bi2 Br3 3.1535(7) 3_565 ?
Bi2 Br1 3.1571(7) . ?
N1 C4 1.315(9) . ?
N1 C1 1.322(9) . ?
N1 C5 1.475(9) . ?
N2 C2 1.327(10) . ?
N2 C3 1.332(10) . ?
N3 C9 1.337(9) . ?
N3 C6 1.346(9) . ?
N3 C10 1.482(10) . ?
N4 C8 1.328(9) . ?
N4 C7 1.347(10) . ?
C1 C2 1.400(10) . ?
C1 H1A 0.95 . ?
C2 H2A 0.95 . ?
C3 C4 1.383(11) . ?
C3 H3A 0.95 . ?
C4 H4A 0.95 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C7 1.367(12) . ?
C6 H6A 0.95 . ?
C7 H7A 0.95 . ?
C8 C9 1.371(10) . ?
C8 H8A 0.95 . ?
C9 H9A 0.95 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 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
Br4 Bi1 Br5 95.92(2) . . ?
Br4 Bi1 Br3 91.94(2) . . ?
Br5 Bi1 Br3 94.21(2) . . ?
Br4 Bi1 Br2 91.18(2) . . ?
Br5 Bi1 Br2 90.93(2) . . ?
Br3 Bi1 Br2 173.68(2) . . ?
Br4 Bi1 Br1 172.01(2) . 3_565 ?
Br5 Bi1 Br1 92.06(2) . 3_565 ?
Br3 Bi1 Br1 87.280(19) . 3_565 ?
Br2 Bi1 Br1 88.870(19) . 3_565 ?
Br4 Bi1 Br1 87.471(19) . . ?
Br5 Bi1 Br1 174.09(2) . . ?
Br3 Bi1 Br1 90.51(2) . . ?
Br2 Bi1 Br1 84.139(18) . . ?
Br1 Bi1 Br1 84.591(18) 3_565 . ?
Br6 Bi2 Br7 94.55(2) . . ?
Br6 Bi2 Br8 91.25(2) . . ?
Br7 Bi2 Br8 93.33(2) . . ?
Br6 Bi2 Br2 176.54(2) . . ?
Br7 Bi2 Br2 88.91(2) . . ?
Br8 Bi2 Br2 88.70(2) . . ?
Br6 Bi2 Br3 92.45(2) . 3_565 ?
Br7 Bi2 Br3 82.85(2) . 3_565 ?
Br8 Bi2 Br3 174.89(2) . 3_565 ?
Br2 Bi2 Br3 87.832(19) . 3_565 ?
Br6 Bi2 Br1 95.69(2) . . ?
Br7 Bi2 Br1 161.95(2) . . ?
Br8 Bi2 Br1 101.26(2) . . ?
Br2 Bi2 Br1 80.931(18) . . ?
Br3 Bi2 Br1 81.898(17) 3_565 . ?
Bi1 Br1 Bi2 92.812(18) 3_565 . ?
Bi1 Br1 Bi1 95.408(18) 3_565 . ?
Bi2 Br1 Bi1 93.754(18) . . ?
Bi1 Br2 Bi2 100.93(2) . . ?
Bi1 Br3 Bi2 97.83(2) . 3_565 ?
C4 N1 C1 121.9(6) . . ?
C4 N1 C5 119.0(6) . . ?
C1 N1 C5 119.0(6) . . ?
C2 N2 C3 116.3(7) . . ?
C9 N3 C6 118.9(7) . . ?
C9 N3 C10 120.4(6) . . ?
C6 N3 C10 120.8(6) . . ?
C8 N4 C7 116.6(7) . . ?
N1 C1 C2 118.1(7) . . ?
N1 C1 H1A 121 . . ?
C2 C1 H1A 121 . . ?
N2 C2 C1 122.4(7) . . ?
N2 C2 H2A 118.8 . . ?
C1 C2 H2A 118.8 . . ?
N2 C3 C4 123.2(7) . . ?
N2 C3 H3A 118.4 . . ?
C4 C3 H3A 118.4 . . ?
N1 C4 C3 118.1(7) . . ?
N1 C4 H4A 121 . . ?
C3 C4 H4A 121 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 119.0(7) . . ?
N3 C6 H6A 120.5 . . ?
C7 C6 H6A 120.5 . . ?
N4 C7 C6 123.0(7) . . ?
N4 C7 H7A 118.5 . . ?
C6 C7 H7A 118.5 . . ?
N4 C8 C9 121.9(7) . . ?
N4 C8 H8A 119.1 . . ?
C9 C8 H8A 119.1 . . ?
N3 C9 C8 120.7(7) . . ?
N3 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1900238'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2019-04-02T20:57:38-00:00
_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 Br18, 2(C5 H8 N2), 2(C5 H7 N2), 3(H2 O)'
_chemical_formula_sum            'C20 H36 Bi4 Br18 N8 O3'
_chemical_formula_weight         2710.87

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.4520(10)
_cell_length_b                   9.7440(4)
_cell_length_c                   22.4625(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.7780(10)
_cell_angle_gamma                90
_cell_volume                     5646.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6720
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      26.9

#----------------------------------------------------------------------------#
#                   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          0.03
_exptl_crystal_density_diffrn    3.189
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             4792

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

_exptl_absorpt_coefficient_mu    25.199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0182
_exptl_absorpt_correction_T_max  0.0504
_exptl_special_details           
;
   55851 Corrected reflections written to file 
C:\frames\Ilyukhin\12_17_1\work\12_17_1_0m.hkl
 Estimated minimum and maximum transmission:  0.0182  0.0504
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  3.0000
;

#----------------------------------------------------------------------------#
#                   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  0.0759
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_number            54121
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.157
_diffrn_reflns_theta_max         30.057
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             8278
_reflns_number_gt                5171
_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-2018/1 (Sheldrick, 2018)'
_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)+(0.0500P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8278
_refine_ls_number_parameters     220
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.096
_refine_ls_R_factor_gt           0.047
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.658
_refine_diff_density_min         -1.231
_refine_diff_density_rms         0.211
_refine_special_details          
;
In 6, one of nine Br atoms as well as one of two [MePz]+ cations are 
disordered with occupancies of 0.63:0.37 and 0.39:0.37:0.24, respectively. 
O atoms of H3O+ and H2O partially occupy five positions 
(0.60, 0.28, 0.26, 0.22 and 0.14). 
Disoredered [MePz]+ cations are restricted geometrically 
(AFIX66 + FLAT + DFIX commands). Disordered Br atom was refined 
anisotropically, while disordered C, N and O atoms were refined isotropically.
;

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.32865(2) 0.43535(4) 0.41081(2) 0.03999(10) Uani 1 1 d . . . . .
Bi2 Bi 0.15734(2) 0.40529(4) 0.36356(2) 0.04341(11) Uani 1 1 d . . . . .
Br1 Br 0.24867(4) 0.25491(9) 0.33380(4) 0.0395(2) Uani 1 1 d . . . . .
Br2 Br 0.23853(4) 0.60253(9) 0.42922(4) 0.0467(2) Uani 1 1 d . . . . .
Br3 Br 0.32883(6) 0.25519(13) 0.52011(5) 0.0782(4) Uani 1 1 d . . . . .
Br4 Br 0.40537(4) 0.26677(12) 0.38567(5) 0.0599(3) Uani 1 1 d . . . . .
Br5 Br 0.33197(5) 0.59272(10) 0.31222(4) 0.0546(3) Uani 1 1 d . . . . .
Br6 Br 0.39579(4) 0.61239(12) 0.48641(5) 0.0594(3) Uani 1 1 d . . . . .
Br7 Br 0.14700(4) 0.53124(10) 0.25257(5) 0.0531(3) Uani 1 1 d . . . . .
Br8 Br 0.08659(4) 0.20993(11) 0.31091(5) 0.0596(3) Uani 1 1 d . . . . .
Br9 Br 0.08292(14) 0.5927(3) 0.38939(14) 0.0658(7) Uani 0.63 1 d . . P . .
Br92 Br 0.0887(2) 0.5460(5) 0.4124(2) 0.0626(11) Uani 0.37 1 d . . P . .
O1 O 0.0712(5) 0.8457(13) 0.2541(6) 0.064(3) Uiso 0.6 1 d . . P A 1
O2 O -0.0035(13) 0.461(3) 0.2655(12) 0.068(8) Uiso 0.28 1 d . . P B 2
O3 O 0 0.630(6) 0.25 0.088(14) Uiso 0.28 2 d S . P C 1
O4 O 0.0111(13) 0.706(4) 0.2310(15) 0.079(10) Uiso 0.26 1 d . . P D 3
O5 O 0.0739(15) 0.825(4) 0.3327(17) 0.078(11) Uiso 0.22 1 d . . P E 3
N1 N 0.2655(4) 0.9279(8) 0.3812(4) 0.054(2) Uani 1 1 d . . . . .
C1 C 0.2282(6) 0.9598(11) 0.4104(5) 0.070(4) Uani 1 1 d . . . . .
H1A H 0.236951 0.998333 0.450161 0.084 Uiso 1 1 calc R U . . .
C2 C 0.1781(6) 0.9373(13) 0.3832(6) 0.073(4) Uani 1 1 d . . . . .
H2A H 0.151589 0.959271 0.40409 0.087 Uiso 1 1 calc R U . . .
N2 N 0.1659(4) 0.8852(9) 0.3282(4) 0.064(3) Uani 1 1 d . . . . .
H2B H 0.133149 0.870175 0.311007 0.077 Uiso 1 1 calc R U . . .
C3 C 0.2013(5) 0.8553(10) 0.2988(5) 0.055(3) Uani 1 1 d . . . . .
H3A H 0.191767 0.817647 0.258911 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2527(4) 0.8780(10) 0.3251(5) 0.055(3) Uani 1 1 d . . . . .
H4A H 0.278775 0.857984 0.303236 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3208(5) 0.9450(12) 0.4099(6) 0.081(4) Uani 1 1 d . . . . .
H5A H 0.324294 0.982655 0.451025 0.122 Uiso 1 1 calc R U . . .
H5B H 0.338158 0.855719 0.412324 0.122 Uiso 1 1 calc R U . . .
H5C H 0.336651 1.007996 0.385298 0.122 Uiso 1 1 calc R U . . .
N3 N 0.4977(11) 0.617(3) 0.3925(13) 0.079(6) Uiso 0.24 1 d DG U P F 1
C6 C 0.4624(14) 0.692(3) 0.3499(12) 0.079(6) Uiso 0.24 1 d DG U P F 1
H6A H 0.447108 0.652959 0.311405 0.094 Uiso 0.24 1 calc R U P F 1
C7 C 0.4494(15) 0.825(3) 0.3635(15) 0.079(6) Uiso 0.24 1 d G U P F 1
H7A H 0.425244 0.87649 0.334333 0.094 Uiso 0.24 1 calc R U P F 1
N4 N 0.4717(15) 0.883(3) 0.4198(16) 0.079(6) Uiso 0.24 1 d G U P F 1
C8 C 0.507(2) 0.808(4) 0.4624(15) 0.079(6) Uiso 0.24 1 d G U P F 1
H8A H 0.522367 0.846966 0.500877 0.094 Uiso 0.24 1 calc R U P F 1
C9 C 0.5201(18) 0.675(4) 0.4488(14) 0.079(6) Uiso 0.24 1 d DG U P F 1
H9A H 0.544233 0.623434 0.477951 0.094 Uiso 0.24 1 calc R U P F 1
C10 C 0.5115(17) 0.480(3) 0.3791(19) 0.079(6) Uiso 0.24 1 d D U P F 1
H10A H 0.53672 0.442664 0.414064 0.118 Uiso 0.24 1 calc R U P F 1
H10B H 0.480445 0.421897 0.370811 0.118 Uiso 0.24 1 calc R U P F 1
H10C H 0.526858 0.480798 0.343129 0.118 Uiso 0.24 1 calc R U P F 1
N32 N 0.4708(7) 0.8226(16) 0.4002(8) 0.080(4) Uiso 0.39 1 d DG U P G 2
C62 C 0.4493(8) 0.742(2) 0.3501(8) 0.080(4) Uiso 0.39 1 d DG U P G 2
H62A H 0.422893 0.777631 0.318247 0.096 Uiso 0.39 1 calc R U P G 2
C72 C 0.4665(9) 0.608(2) 0.3465(9) 0.080(4) Uiso 0.39 1 d G U P G 2
H72A H 0.451817 0.55216 0.312276 0.096 Uiso 0.39 1 calc R U P G 2
N42 N 0.5051(9) 0.5547(17) 0.3931(10) 0.080(4) Uiso 0.39 1 d G U P G 2
C82 C 0.5266(9) 0.636(2) 0.4433(10) 0.080(4) Uiso 0.39 1 d G U P G 2
H82A H 0.552974 0.599661 0.475135 0.096 Uiso 0.39 1 calc R U P G 2
C92 C 0.5094(9) 0.770(2) 0.4468(8) 0.080(4) Uiso 0.39 1 d DG U P G 2
H92A H 0.52405 0.825133 0.481108 0.096 Uiso 0.39 1 calc R U P G 2
C102 C 0.4541(11) 0.9608(19) 0.4057(13) 0.080(4) Uiso 0.39 1 d D U P G 2
H10D H 0.473745 1.000524 0.443963 0.121 Uiso 0.39 1 calc R U P G 2
H10E H 0.46016 1.015117 0.371198 0.121 Uiso 0.39 1 calc R U P G 2
H10F H 0.417068 0.961598 0.405665 0.121 Uiso 0.39 1 calc R U P G 2
N33 N 0.4849(6) 0.6809(13) 0.3874(6) 0.056(3) Uiso 0.37 1 d DG U P H 3
C63 C 0.5136(8) 0.7045(16) 0.4462(7) 0.056(3) Uiso 0.37 1 d DG U P H 3
H63A H 0.534821 0.633925 0.467735 0.068 Uiso 0.37 1 calc R U P H 3
C73 C 0.5111(9) 0.8315(19) 0.4737(7) 0.056(3) Uiso 0.37 1 d G U P H 3
H73A H 0.530642 0.847674 0.513887 0.068 Uiso 0.37 1 calc R U P H 3
N43 N 0.4800(8) 0.9348(14) 0.4422(8) 0.056(3) Uiso 0.37 1 d G U P H 3
C83 C 0.4514(8) 0.9111(15) 0.3833(8) 0.056(3) Uiso 0.37 1 d G U P H 3
H83A H 0.430098 0.981725 0.361836 0.068 Uiso 0.37 1 calc R U P H 3
C93 C 0.4538(7) 0.7842(17) 0.3559(6) 0.056(3) Uiso 0.37 1 d DG U P H 3
H93A H 0.434276 0.767977 0.315683 0.068 Uiso 0.37 1 calc R U P H 3
C103 C 0.4860(9) 0.5515(17) 0.3569(10) 0.056(3) Uiso 0.37 1 d D U P H 3
H10G H 0.463333 0.556074 0.31609 0.085 Uiso 0.37 1 calc R U P H 3
H10H H 0.521562 0.531548 0.353407 0.085 Uiso 0.37 1 calc R U P H 3
H10I H 0.473947 0.478822 0.380533 0.085 Uiso 0.37 1 calc R U P H 3



#----------------------------------------------------------------------------#
#                   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 Br5 2.7110(10) . ?
Bi1 Br4 2.7644(12) . ?
Bi1 Br6 2.7711(10) . ?
Bi1 Br1 2.9902(9) . ?
Bi1 Br2 2.9907(11) . ?
Bi1 Br3 3.0173(11) . ?
Bi2 Br92 2.695(5) . ?
Bi2 Br7 2.7377(10) . ?
Bi2 Br8 2.7468(10) . ?
Bi2 Br9 2.837(3) . ?
Bi2 Br3 2.9974(11) 7_556 ?
Bi2 Br2 3.0133(10) . ?
Bi2 Br1 3.0239(10) . ?
Br9 Br92 0.680(4) . ?
N1 C4 1.323(12) . ?
N1 C1 1.335(15) . ?
N1 C5 1.472(15) . ?
C1 C2 1.348(18) . ?
C1 H1A 0.95 . ?
C2 N2 1.308(15) . ?
C2 H2A 0.95 . ?
N2 C3 1.293(13) . ?
N2 H2B 0.88 . ?
C3 C4 1.375(15) . ?
C3 H3A 0.95 . ?
C4 H4A 0.95 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
N3 C6 1.39 . ?
N3 C9 1.39 . ?
N3 C10 1.438(9) . ?
C6 C7 1.39 . ?
C6 H6A 0.95 . ?
C7 N4 1.39 . ?
C7 H7A 0.95 . ?
N4 C8 1.39 . ?
C8 C9 1.39 . ?
C8 H8A 0.95 . ?
C9 H9A 0.95 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
N32 C62 1.39 . ?
N32 C92 1.39 . ?
N32 C102 1.431(8) . ?
C62 C72 1.39 . ?
C62 H62A 0.95 . ?
C72 N42 1.39 . ?
C72 H72A 0.95 . ?
N42 C82 1.39 . ?
C82 C92 1.39 . ?
C82 H82A 0.95 . ?
C92 H92A 0.95 . ?
C102 H10D 0.98 . ?
C102 H10E 0.98 . ?
C102 H10F 0.98 . ?
N33 C63 1.39 . ?
N33 C93 1.39 . ?
N33 C103 1.437(8) . ?
C63 C73 1.39 . ?
C63 H63A 0.95 . ?
C73 N43 1.39 . ?
C73 H73A 0.95 . ?
N43 C83 1.39 . ?
C83 C93 1.39 . ?
C83 H83A 0.95 . ?
C93 H93A 0.95 . ?
C103 H10G 0.98 . ?
C103 H10H 0.98 . ?
C103 H10I 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
Br5 Bi1 Br4 90.65(4) . . ?
Br5 Bi1 Br6 90.94(3) . . ?
Br4 Bi1 Br6 95.47(4) . . ?
Br5 Bi1 Br1 90.38(3) . . ?
Br4 Bi1 Br1 89.42(3) . . ?
Br6 Bi1 Br1 174.93(3) . . ?
Br5 Bi1 Br2 88.60(3) . . ?
Br4 Bi1 Br2 174.57(3) . . ?
Br6 Bi1 Br2 89.92(3) . . ?
Br1 Bi1 Br2 85.21(3) . . ?
Br5 Bi1 Br3 177.80(4) . . ?
Br4 Bi1 Br3 87.21(4) . . ?
Br6 Bi1 Br3 88.75(3) . . ?
Br1 Bi1 Br3 90.12(3) . . ?
Br2 Bi1 Br3 93.57(4) . . ?
Br92 Bi2 Br7 101.66(10) . . ?
Br92 Bi2 Br8 94.11(11) . . ?
Br7 Bi2 Br8 89.84(3) . . ?
Br92 Bi2 Br9 13.81(9) . . ?
Br7 Bi2 Br9 87.91(6) . . ?
Br8 Bi2 Br9 95.54(8) . . ?
Br92 Bi2 Br3 82.75(11) . 7_556 ?
Br7 Bi2 Br3 174.95(4) . 7_556 ?
Br8 Bi2 Br3 87.36(3) . 7_556 ?
Br9 Bi2 Br3 96.54(6) . 7_556 ?
Br92 Bi2 Br2 87.00(11) . . ?
Br7 Bi2 Br2 94.39(3) . . ?
Br8 Bi2 Br2 175.32(4) . . ?
Br9 Bi2 Br2 86.62(8) . . ?
Br3 Bi2 Br2 88.27(3) 7_556 . ?
Br92 Bi2 Br1 168.44(11) . . ?
Br7 Bi2 Br1 86.54(3) . . ?
Br8 Bi2 Br1 94.05(3) . . ?
Br9 Bi2 Br1 168.91(7) . . ?
Br3 Bi2 Br1 89.46(3) 7_556 . ?
Br2 Bi2 Br1 84.23(3) . . ?
Bi1 Br1 Bi2 94.87(3) . . ?
Bi1 Br2 Bi2 95.08(3) . . ?
Bi2 Br3 Bi1 172.22(5) 7_556 . ?
Br92 Br9 Bi2 71.1(6) . . ?
Br9 Br92 Bi2 95.1(6) . . ?
C4 N1 C1 119.6(11) . . ?
C4 N1 C5 118.5(10) . . ?
C1 N1 C5 122.0(10) . . ?
N1 C1 C2 119.9(11) . . ?
N1 C1 H1A 120 . . ?
C2 C1 H1A 120 . . ?
N2 C2 C1 120.1(12) . . ?
N2 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C3 N2 C2 121.0(12) . . ?
C3 N2 H2B 119.5 . . ?
C2 N2 H2B 119.5 . . ?
N2 C3 C4 120.3(10) . . ?
N2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
N1 C4 C3 119.1(10) . . ?
N1 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 N3 C9 120 . . ?
C6 N3 C10 120.6(11) . . ?
C9 N3 C10 119.4(11) . . ?
N3 C6 C7 120 . . ?
N3 C6 H6A 120 . . ?
C7 C6 H6A 120 . . ?
N4 C7 C6 120 . . ?
N4 C7 H7A 120 . . ?
C6 C7 H7A 120 . . ?
C7 N4 C8 120 . . ?
C9 C8 N4 120 . . ?
C9 C8 H8A 120 . . ?
N4 C8 H8A 120 . . ?
C8 C9 N3 120 . . ?
C8 C9 H9A 120 . . ?
N3 C9 H9A 120 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C62 N32 C92 120 . . ?
C62 N32 C102 121.8(10) . . ?
C92 N32 C102 118.2(10) . . ?
N32 C62 C72 120 . . ?
N32 C62 H62A 120 . . ?
C72 C62 H62A 120 . . ?
N42 C72 C62 120 . . ?
N42 C72 H72A 120 . . ?
C62 C72 H72A 120 . . ?
C72 N42 C82 120 . . ?
N42 C82 C92 120 . . ?
N42 C82 H82A 120 . . ?
C92 C82 H82A 120 . . ?
C82 C92 N32 120 . . ?
C82 C92 H92A 120 . . ?
N32 C92 H92A 120 . . ?
N32 C102 H10D 109.5 . . ?
N32 C102 H10E 109.5 . . ?
H10D C102 H10E 109.5 . . ?
N32 C102 H10F 109.5 . . ?
H10D C102 H10F 109.5 . . ?
H10E C102 H10F 109.5 . . ?
C63 N33 C93 120 . . ?
C63 N33 C103 122.3(10) . . ?
C93 N33 C103 117.7(10) . . ?
C73 C63 N33 120 . . ?
C73 C63 H63A 120 . . ?
N33 C63 H63A 120 . . ?
C63 C73 N43 120 . . ?
C63 C73 H73A 120 . . ?
N43 C73 H73A 120 . . ?
C83 N43 C73 120 . . ?
N43 C83 C93 120 . . ?
N43 C83 H83A 120 . . ?
C93 C83 H83A 120 . . ?
C83 C93 N33 120 . . ?
C83 C93 H93A 120 . . ?
N33 C93 H93A 120 . . ?
N33 C103 H10G 109.5 . . ?
N33 C103 H10H 109.5 . . ?
H10G C103 H10H 109.5 . . ?
N33 C103 H10I 109.5 . . ?
H10G C103 H10I 109.5 . . ?
H10H C103 H10I 109.5 . . ?

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
_geom_hbond_publ_flag
C1 H1A Br2 0.95 2.82 3.568(12) 136.3 7_566 yes
C1 H1A Br3 0.95 3.12 3.670(11) 118.3 7_566 yes
C2 H2A Br6 0.95 3.08 3.894(12) 144.9 7_566 yes
N2 H2B O1a 0.88 1.86 2.712(16) 163.3 . yes
N2 H2B O5c 0.88 1.8 2.53(4) 139.1 . yes
C3 H3A Br1 0.95 2.94 3.651(10) 132.6 4 yes
C3 H3A Br7 0.95 3.02 3.529(10) 114.9 . yes
C4 H4A Br5 0.95 2.93 3.531(10) 122.5 . yes
C4 H4A Br7 0.95 3.06 3.789(10) 134.6 4 yes
C6a H6Aa Br8 0.95 2.75 3.56(3) 143.7 4 yes
C7a H7Aa Br7 0.95 2.84 3.79(2) 179.7 4 yes
C8a H8Aa Br4 0.95 3.04 3.75(3) 132.7 5_666 yes
C9a H9Aa Br6 0.95 2.81 3.67(3) 151.6 5_666 yes
C10a H10Ca Br8 0.98 2.92 3.56(5) 123.9 3 yes
C62b H62Ab Br8 0.95 2.93 3.544(17) 123.3 4 yes
C72b H72Ab Br8 0.95 3.13 3.64(2) 115.6 4 yes
C82b H82Ab Br6 0.95 2.52 3.335(15) 144.4 5_666 yes
C63c H63Ac Br6 0.95 3.06 3.996(12) 169.5 5_666 yes
C73c H73Ac Br4 0.95 2.74 3.563(14) 145.4 5_666 yes
C73c H73Ac N43c 0.95 2.38 2.94(3) 116.9 5_676 yes
C83c H83Ac Br4 0.95 2.93 3.677(13) 136.4 1_565 yes
C83c H83Ac Br7 0.95 2.95 3.734(14) 141.2 4 yes
C93c H93Ac Br8 0.95 2.83 3.733(13) 158.9 4 yes

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1900236'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2016-11-30T11:25:22-00:00
_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         '3(C8 H14 N2), 2(Bi Br6), H2 O'
_chemical_formula_sum            'C24 H44 Bi2 Br12 N6 O'
_chemical_formula_weight         1809.53
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P c'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_Int_Tables_number      7
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.0371(6)
_cell_length_b                   13.4220(7)
_cell_length_c                   15.1336(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.014(2)
_cell_angle_gamma                90
_cell_volume                     2241.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5178
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.31

_shelx_space_group_comment       
;
Compound 4 possesses space group Pc with angle \b equal to 90.014(2)? which 
results in the pseudomerohedral and centrosymmetric twinning with domain 
ratio of 0.280(16): 0.237(16) : 0.263(16) : 0.221(16). 
;
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    2.681
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1648

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

_exptl_absorpt_coefficient_mu    18.561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0273
_exptl_absorpt_correction_T_max  0.0943
_exptl_special_details           
;
   27302 Corrected reflections written to file 11_25_2_0m.hkl
 Estimated minimum and maximum transmission:  0.0273  0.0943
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  2.0000
 Lambda/2 correction factor = 0.00150
;

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

_diffrn_ambient_temperature      120(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  0.0613
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_number            27279
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         27.152
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_coverage         0.997
_reflns_number_total             9873
_reflns_number_gt                8246
_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-2014/7 (Sheldrick, 2014)'
_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 4-component twin.,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)+(0.0500P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9873
_refine_ls_number_parameters     290
_refine_ls_number_restraints     302
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.003
_refine_ls_abs_structure_details 
;
 Flack x determined using 0 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0
_refine_diff_density_max         3.555
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.229

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#
_reflns_special_details          
;
Two of three cations are disordered with 1:1 ratio. Disordered cations are 
restricted geometrically (SAME command), all disordered atoms are refined 
isotropically. 
;

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.00007(7) 0.75322(5) -0.00052(10) 0.01863(18) Uani 1 1 d . . . . .
Bi2 Bi 0.46922(7) 0.76527(5) 0.49709(12) 0.0220(2) Uani 1 1 d . . . . .
Br1 Br -0.1733(6) 0.7152(4) 0.1415(3) 0.0366(12) Uani 1 1 d . . . . .
Br2 Br -0.1781(6) 0.7076(5) -0.1350(4) 0.0498(17) Uani 1 1 d . . . . .
Br3 Br 0.1772(4) 0.7848(5) 0.1276(4) 0.054(2) Uani 1 1 d . . . . .
Br4 Br 0.0626(2) 0.54467(15) 0.0003(5) 0.0332(5) Uani 1 1 d . . . . .
Br5 Br 0.1745(6) 0.7830(6) -0.1296(3) 0.058(2) Uani 1 1 d . . . . .
Br6 Br -0.0615(2) 0.95814(15) -0.0006(5) 0.0447(7) Uani 1 1 d . . . . .
Br7 Br 0.6339(5) 0.8204(5) 0.6323(3) 0.0313(13) Uani 1 1 d . . . . .
Br8 Br 0.6320(6) 0.8210(4) 0.3601(3) 0.0335(13) Uani 1 1 d . . . . .
Br9 Br 0.3021(5) 0.6970(4) 0.3639(3) 0.0325(13) Uani 1 1 d . . . . .
Br10 Br 0.3042(6) 0.7029(5) 0.6332(3) 0.0388(15) Uani 1 1 d . . . . .
Br11 Br 0.3492(2) 0.94945(16) 0.4930(5) 0.0373(7) Uani 1 1 d . . . . .
Br12 Br 0.58231(18) 0.56749(13) 0.4980(4) 0.0258(4) Uani 1 1 d . . . . .
O1 O 0.3230(19) 0.4598(14) 0.4057(12) 0.040(5) Uani 1 1 d . . . . .
H1 H 0.2443 0.4569 0.4334 0.048 Uiso 1 1 d R U . . .
H2 H 0.3171 0.5254 0.3941 0.048 Uiso 1 1 d R U . . .
N1 N 0.5576(12) 0.1712(9) 0.5681(8) 0.029(6) Uani 1 1 d DG U . . .
C1 C 0.5547(12) 0.1772(8) 0.4764(7) 0.024(6) Uani 1 1 d DG U . . .
C2 C 0.4973(14) 0.2571(10) 0.4355(6) 0.033(6) Uani 1 1 d DG U . . .
N2 N 0.4428(10) 0.3308(8) 0.4863(8) 0.022(4) Uani 1 1 d DG U . . .
H3 H 0.4065 0.3814 0.4604 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4457(14) 0.3248(9) 0.5780(8) 0.023(5) Uani 1 1 d DG U . . .
C4 C 0.5031(17) 0.2449(11) 0.6188(6) 0.035(7) Uani 1 1 d DG U . . .
H4A H 0.5051 0.2408 0.6815 0.043 Uiso 1 1 calc R U . . .
C5 C 0.623(4) 0.091(2) 0.612(2) 0.064(12) Uani 1 1 d D U . . .
H5A H 0.6156 0.0982 0.6759 0.095 Uiso 1 1 calc R U . . .
H5B H 0.5891 0.0267 0.5935 0.095 Uiso 1 1 calc R U . . .
H5C H 0.7088 0.0938 0.595 0.095 Uiso 1 1 calc R U . . .
C6 C 0.613(3) 0.0965(19) 0.4193(17) 0.034(8) Uani 1 1 d D U . . .
H6A H 0.6494 0.0457 0.4575 0.051 Uiso 1 1 calc R U . . .
H6B H 0.551 0.0657 0.3818 0.051 Uiso 1 1 calc R U . . .
H6C H 0.6758 0.1264 0.3821 0.051 Uiso 1 1 calc R U . . .
C7 C 0.492(3) 0.271(2) 0.3423(13) 0.047(9) Uani 1 1 d D U . . .
H7A H 0.5322 0.2154 0.3126 0.07 Uiso 1 1 calc R U . . .
H7B H 0.4066 0.2737 0.3236 0.07 Uiso 1 1 calc R U . . .
H7C H 0.5319 0.3336 0.3266 0.07 Uiso 1 1 calc R U . . .
C8 C 0.383(2) 0.4069(18) 0.6299(14) 0.034(7) Uani 1 1 d D U . . .
H8A H 0.3916 0.3939 0.6934 0.051 Uiso 1 1 calc R U . . .
H8B H 0.4201 0.4712 0.6156 0.051 Uiso 1 1 calc R U . . .
H8C H 0.2968 0.4085 0.6144 0.051 Uiso 1 1 calc R U . . .
N3 N 1.047(2) -0.088(2) 0.305(2) 0.0251(16) Uiso 0.5 1 d DG U P A 1
C9 C 0.993(2) -0.011(2) 0.258(2) 0.0251(16) Uiso 0.5 1 d DG U P A 1
C10 C 1.063(3) 0.060(2) 0.216(2) 0.0251(16) Uiso 0.5 1 d DG U P A 1
N4 N 1.189(3) 0.055(2) 0.221(2) 0.0251(16) Uiso 0.5 1 d DG U P A 1
H4 H 1.2337 0.0999 0.1947 0.03 Uiso 0.5 1 calc R U P A 1
C11 C 1.244(2) -0.022(2) 0.269(2) 0.0251(16) Uiso 0.5 1 d DG U P A 1
C12 C 1.173(2) -0.093(2) 0.311(2) 0.0251(16) Uiso 0.5 1 d DG U P A 1
H12A H 1.2102 -0.145 0.3434 0.03 Uiso 0.5 1 calc R U P A 1
C13 C 0.980(4) -0.176(3) 0.333(4) 0.0251(16) Uiso 0.5 1 d D U P A 1
H13A H 1.0342 -0.221 0.3653 0.038 Uiso 0.5 1 calc R U P A 1
H13B H 0.9126 -0.1564 0.3708 0.038 Uiso 0.5 1 calc R U P A 1
H13C H 0.9488 -0.2104 0.2804 0.038 Uiso 0.5 1 calc R U P A 1
C14 C 0.857(3) 0.005(6) 0.263(6) 0.0251(16) Uiso 0.5 1 d D U P A 1
H14A H 0.8341 0.0617 0.2259 0.038 Uiso 0.5 1 calc R U P A 1
H14B H 0.8143 -0.0548 0.243 0.038 Uiso 0.5 1 calc R U P A 1
H14C H 0.8338 0.0193 0.3247 0.038 Uiso 0.5 1 calc R U P A 1
C15 C 1.016(4) 0.133(3) 0.156(3) 0.0251(16) Uiso 0.5 1 d D U P A 1
H15A H 0.9277 0.1311 0.1571 0.038 Uiso 0.5 1 calc R U P A 1
H15B H 1.044 0.1995 0.1748 0.038 Uiso 0.5 1 calc R U P A 1
H15C H 1.0456 0.1194 0.0964 0.038 Uiso 0.5 1 calc R U P A 1
C16 C 1.381(3) -0.029(4) 0.270(4) 0.0251(16) Uiso 0.5 1 d D U P A 1
H16A H 1.4152 0.0277 0.2372 0.038 Uiso 0.5 1 calc R U P A 1
H16B H 1.4096 -0.0267 0.3313 0.038 Uiso 0.5 1 calc R U P A 1
H16C H 1.4062 -0.0912 0.2423 0.038 Uiso 0.5 1 calc R U P A 1
N32 N 1.063(2) 0.083(2) 0.197(3) 0.0251(16) Uiso 0.5 1 d DG U P B 2
C92 C 0.997(2) 0.015(2) 0.247(3) 0.0251(16) Uiso 0.5 1 d DG U P B 2
C102 C 1.057(2) -0.060(2) 0.292(2) 0.0251(16) Uiso 0.5 1 d DG U P B 2
N42 N 1.183(2) -0.067(3) 0.288(2) 0.0251(16) Uiso 0.5 1 d DG U P B 2
H5 H 1.2212 -0.1142 0.3173 0.03 Uiso 0.5 1 calc R U P B 2
C112 C 1.248(2) 0.002(3) 0.239(3) 0.0251(16) Uiso 0.5 1 d DG U P B 2
C122 C 1.188(2) 0.077(3) 0.193(3) 0.0251(16) Uiso 0.5 1 d DG U P B 2
H12B H 1.2328 0.1237 0.1592 0.03 Uiso 0.5 1 calc R U P B 2
C132 C 1.004(4) 0.161(4) 0.145(3) 0.0251(16) Uiso 0.5 1 d D U P B 2
H13D H 0.9958 0.221 0.1806 0.038 Uiso 0.5 1 d R U P B 2
H13E H 0.9238 0.1375 0.1264 0.038 Uiso 0.5 1 d R U P B 2
H13F H 1.0529 0.1755 0.0922 0.038 Uiso 0.5 1 d R U P B 2
C142 C 0.860(3) 0.023(5) 0.255(6) 0.0251(16) Uiso 0.5 1 d D U P B 2
H14D H 0.8304 -0.0363 0.2864 0.038 Uiso 0.5 1 d R U P B 2
H14E H 0.8248 0.0256 0.1961 0.038 Uiso 0.5 1 d R U P B 2
H14F H 0.838 0.0827 0.2885 0.038 Uiso 0.5 1 d R U P B 2
C152 C 0.997(4) -0.146(3) 0.328(4) 0.0251(16) Uiso 0.5 1 d D U P B 2
H15D H 1.0555 -0.2005 0.3342 0.038 Uiso 0.5 1 d R U P B 2
H15E H 0.9319 -0.1666 0.2877 0.038 Uiso 0.5 1 d R U P B 2
H15F H 0.963 -0.1292 0.3855 0.038 Uiso 0.5 1 d R U P B 2
C162 C 1.384(3) -0.012(4) 0.227(3) 0.0251(16) Uiso 0.5 1 d D U P B 2
H16D H 1.4176 0.0476 0.1985 0.038 Uiso 0.5 1 d R U P B 2
H16E H 1.3992 -0.0702 0.1895 0.038 Uiso 0.5 1 d R U P B 2
H16F H 1.4224 -0.0216 0.2846 0.038 Uiso 0.5 1 d R U P B 2
N5 N 0.764(2) 0.539(3) 0.284(3) 0.0251(16) Uiso 0.5 1 d DG U P C 1
C17 C 0.863(2) 0.498(4) 0.240(3) 0.0251(16) Uiso 0.5 1 d DG U P C 1
C18 C 0.980(2) 0.523(4) 0.267(3) 0.0251(16) Uiso 0.5 1 d DG U P C 1
N6 N 0.998(2) 0.588(3) 0.337(3) 0.0251(16) Uiso 0.5 1 d DG U P C 1
H6 H 1.0715 0.604 0.3535 0.03 Uiso 0.5 1 calc R U P C 1
C19 C 0.898(3) 0.629(4) 0.380(3) 0.0251(16) Uiso 0.5 1 d DG U P C 1
C20 C 0.782(2) 0.604(4) 0.354(3) 0.0251(16) Uiso 0.5 1 d DG U P C 1
H20A H 0.7138 0.6317 0.3839 0.03 Uiso 0.5 1 calc R U P C 1
C21 C 0.640(3) 0.519(5) 0.255(4) 0.0251(16) Uiso 0.5 1 d D U P C 1
H21A H 0.6397 0.4576 0.22 0.038 Uiso 0.5 1 d R U P C 1
H21B H 0.6101 0.5743 0.219 0.038 Uiso 0.5 1 d R U P C 1
H21C H 0.5883 0.5105 0.307 0.038 Uiso 0.5 1 d R U P C 1
C22 C 0.846(3) 0.429(4) 0.162(3) 0.0251(16) Uiso 0.5 1 d D U P C 1
H22A H 0.7812 0.3809 0.1747 0.038 Uiso 0.5 1 d R U P C 1
H22B H 0.9214 0.3932 0.1503 0.038 Uiso 0.5 1 d R U P C 1
H22C H 0.8235 0.4681 0.1095 0.038 Uiso 0.5 1 d R U P C 1
C23 C 1.084(3) 0.467(3) 0.239(3) 0.0251(16) Uiso 0.5 1 d D U P C 1
H23A H 1.1566 0.4944 0.2677 0.038 Uiso 0.5 1 d R U P C 1
H23B H 1.0918 0.4729 0.175 0.038 Uiso 0.5 1 d R U P C 1
H23C H 1.0747 0.3969 0.2556 0.038 Uiso 0.5 1 d R U P C 1
C24 C 0.918(3) 0.697(4) 0.460(3) 0.0251(16) Uiso 0.5 1 d D U P C 1
H24A H 0.8565 0.7491 0.4601 0.038 Uiso 0.5 1 d R U P C 1
H24B H 0.9989 0.727 0.4561 0.038 Uiso 0.5 1 d R U P C 1
H24C H 0.9123 0.6578 0.5146 0.038 Uiso 0.5 1 d R U P C 1
N52 N 0.9911(19) 0.531(3) 0.278(3) 0.0251(16) Uiso 0.5 1 d DG U P D 2
C172 C 0.883(2) 0.494(4) 0.244(3) 0.0251(16) Uiso 0.5 1 d DG U P D 2
C182 C 0.7731(19) 0.525(4) 0.280(3) 0.0251(16) Uiso 0.5 1 d DG U P D 2
N62 N 0.772(2) 0.594(4) 0.348(3) 0.0251(16) Uiso 0.5 1 d DG U P D 2
H7 H 0.7025 0.6145 0.3707 0.03 Uiso 0.5 1 calc R U P D 2
C192 C 0.880(3) 0.632(4) 0.382(3) 0.0251(16) Uiso 0.5 1 d DG U P D 2
C202 C 0.990(2) 0.600(4) 0.346(3) 0.0251(16) Uiso 0.5 1 d DG U P D 2
H20B H 1.064 0.6251 0.3689 0.03 Uiso 0.5 1 calc R U P D 2
C212 C 1.107(2) 0.497(6) 0.243(5) 0.0251(16) Uiso 0.5 1 d D U P D 2
H21D H 1.099 0.4878 0.1794 0.038 Uiso 0.5 1 d R U P D 2
H21E H 1.1316 0.4341 0.2708 0.038 Uiso 0.5 1 d R U P D 2
H21F H 1.1688 0.548 0.2552 0.038 Uiso 0.5 1 d R U P D 2
C222 C 0.880(3) 0.431(5) 0.161(3) 0.0251(16) Uiso 0.5 1 d D U P D 2
H22D H 0.7957 0.4112 0.1483 0.038 Uiso 0.5 1 d R U P D 2
H22E H 0.9288 0.3708 0.1702 0.038 Uiso 0.5 1 d R U P D 2
H22F H 0.912 0.4685 0.1108 0.038 Uiso 0.5 1 d R U P D 2
C232 C 0.661(3) 0.512(5) 0.234(2) 0.0251(16) Uiso 0.5 1 d D U P D 2
H23D H 0.6589 0.4462 0.2062 0.038 Uiso 0.5 1 d R U P D 2
H23E H 0.654 0.5636 0.1882 0.038 Uiso 0.5 1 d R U P D 2
H23F H 0.5925 0.5183 0.2751 0.038 Uiso 0.5 1 d R U P D 2
C242 C 0.876(4) 0.695(4) 0.465(3) 0.0251(16) Uiso 0.5 1 d D U P D 2
H24D H 0.9428 0.7428 0.4643 0.038 Uiso 0.5 1 d R U P D 2
H24E H 0.8842 0.6518 0.5175 0.038 Uiso 0.5 1 d R U P D 2
H24F H 0.7987 0.7302 0.4679 0.038 Uiso 0.5 1 d R U P D 2



#----------------------------------------------------------------------------#
#                   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 Br5 2.773(6) . ?
Bi1 Br3 2.787(5) . ?
Bi1 Br6 2.833(2) . ?
Bi1 Br4 2.883(2) . ?
Bi1 Br2 2.894(6) . ?
Bi1 Br1 2.921(6) . ?
Bi2 Br11 2.805(2) . ?
Bi2 Br7 2.835(5) . ?
Bi2 Br8 2.844(6) . ?
Bi2 Br10 2.874(5) . ?
Bi2 Br9 2.882(5) . ?
Bi2 Br12 2.933(2) . ?
O1 H1 0.9653 . ?
O1 H2 0.9 . ?
N1 C1 1.39 . ?
N1 C4 1.39 . ?
N1 C5 1.46(2) . ?
C1 C2 1.39 . ?
C1 C6 1.528(16) . ?
C2 N2 1.39 . ?
C2 C7 1.424(19) . ?
N2 C3 1.39 . ?
N2 H3 0.88 . ?
C3 C4 1.39 . ?
C3 C8 1.522(16) . ?
C4 H4A 0.95 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
N3 C9 1.39 . ?
N3 C12 1.39 . ?
N3 C13 1.46(2) . ?
C9 C10 1.39 . ?
C9 C14 1.518(17) . ?
C10 N4 1.39 . ?
C10 C15 1.43(2) . ?
N4 C11 1.39 . ?
N4 H4 0.88 . ?
C11 C12 1.39 . ?
C11 C16 1.517(17) . ?
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 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
N32 C92 1.39 . ?
N32 C122 1.39 . ?
N32 C132 1.46(2) . ?
C92 C102 1.39 . ?
C92 C142 1.519(16) . ?
C102 N42 1.39 . ?
C102 C152 1.43(2) . ?
N42 C112 1.39 . ?
N42 H5 0.88 . ?
C112 C122 1.39 . ?
C112 C162 1.518(17) . ?
C122 H12B 0.95 . ?
C132 H13D 0.98 . ?
C132 H13E 0.98 . ?
C132 H13F 0.98 . ?
C142 H14D 0.98 . ?
C142 H14E 0.98 . ?
C142 H14F 0.98 . ?
C152 H15D 0.98 . ?
C152 H15E 0.98 . ?
C152 H15F 0.98 . ?
C162 H16D 0.98 . ?
C162 H16E 0.98 . ?
C162 H16F 0.98 . ?
N5 C17 1.39 . ?
N5 C20 1.39 . ?
N5 C21 1.46(2) . ?
C17 C18 1.39 . ?
C17 C22 1.521(17) . ?
C18 N6 1.39 . ?
C18 C23 1.43(2) . ?
N6 C19 1.39 . ?
N6 H6 0.88 . ?
C19 C20 1.39 . ?
C19 C24 1.525(17) . ?
C20 H20A 0.95 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
N52 C172 1.39 . ?
N52 C202 1.39 . ?
N52 C212 1.45(2) . ?
C172 C182 1.39 . ?
C172 C222 1.522(17) . ?
C182 N62 1.39 . ?
C182 C232 1.43(2) . ?
N62 C192 1.39 . ?
N62 H7 0.88 . ?
C192 C202 1.39 . ?
C192 C242 1.526(17) . ?
C202 H20B 0.95 . ?
C212 H21D 0.98 . ?
C212 H21E 0.98 . ?
C212 H21F 0.98 . ?
C222 H22D 0.98 . ?
C222 H22E 0.98 . ?
C222 H22F 0.98 . ?
C232 H23D 0.98 . ?
C232 H23E 0.98 . ?
C232 H23F 0.98 . ?
C242 H24D 0.98 . ?
C242 H24E 0.98 . ?
C242 H24F 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
Br5 Bi1 Br3 88.85(10) . . ?
Br5 Bi1 Br6 91.5(2) . . ?
Br3 Bi1 Br6 91.20(19) . . ?
Br5 Bi1 Br4 88.65(19) . . ?
Br3 Bi1 Br4 88.62(17) . . ?
Br6 Bi1 Br4 179.8(2) . . ?
Br5 Bi1 Br2 90.4(2) . . ?
Br3 Bi1 Br2 176.32(18) . . ?
Br6 Bi1 Br2 92.43(17) . . ?
Br4 Bi1 Br2 87.76(16) . . ?
Br5 Bi1 Br1 176.59(19) . . ?
Br3 Bi1 Br1 88.54(19) . . ?
Br6 Bi1 Br1 90.77(17) . . ?
Br4 Bi1 Br1 89.09(16) . . ?
Br2 Bi1 Br1 92.06(10) . . ?
Br11 Bi2 Br7 95.08(17) . . ?
Br11 Bi2 Br8 92.90(17) . . ?
Br7 Bi2 Br8 93.01(7) . . ?
Br11 Bi2 Br10 88.47(18) . . ?
Br7 Bi2 Br10 88.01(19) . . ?
Br8 Bi2 Br10 178.22(19) . . ?
Br11 Bi2 Br9 87.86(17) . . ?
Br7 Bi2 Br9 176.49(18) . . ?
Br8 Bi2 Br9 88.74(18) . . ?
Br10 Bi2 Br9 90.16(8) . . ?
Br11 Bi2 Br12 176.84(9) . . ?
Br7 Bi2 Br12 87.71(16) . . ?
Br8 Bi2 Br12 88.43(16) . . ?
Br10 Bi2 Br12 90.15(16) . . ?
Br9 Bi2 Br12 89.30(15) . . ?
H1 O1 H2 93.4 . . ?
C1 N1 C4 120 . . ?
C1 N1 C5 120.5(14) . . ?
C4 N1 C5 119.4(14) . . ?
C2 C1 N1 120 . . ?
C2 C1 C6 119.1(12) . . ?
N1 C1 C6 120.9(12) . . ?
N2 C2 C1 120 . . ?
N2 C2 C7 115.8(13) . . ?
C1 C2 C7 124.2(13) . . ?
C2 N2 C3 120 . . ?
C2 N2 H3 120 . . ?
C3 N2 H3 120 . . ?
N2 C3 C4 120 . . ?
N2 C3 C8 117.6(12) . . ?
C4 C3 C8 122.4(12) . . ?
C3 C4 N1 120 . . ?
C3 C4 H4A 120 . . ?
N1 C4 H4A 120 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 N3 C12 120 . . ?
C9 N3 C13 121.7(16) . . ?
C12 N3 C13 116.7(15) . . ?
N3 C9 C10 120 . . ?
N3 C9 C14 120.6(15) . . ?
C10 C9 C14 118.6(16) . . ?
N4 C10 C9 120 . . ?
N4 C10 C15 115.5(15) . . ?
C9 C10 C15 124.0(15) . . ?
C10 N4 C11 120 . . ?
C10 N4 H4 120 . . ?
C11 N4 H4 120 . . ?
C12 C11 N4 120 . . ?
C12 C11 C16 120.9(15) . . ?
N4 C11 C16 119.0(15) . . ?
C11 C12 N3 120 . . ?
C11 C12 H12A 120 . . ?
N3 C12 H12A 120 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.4 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.4 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C92 N32 C122 120 . . ?
C92 N32 C132 122.5(15) . . ?
C122 N32 C132 117.5(15) . . ?
C102 C92 N32 120 . . ?
C102 C92 C142 119.0(15) . . ?
N32 C92 C142 121.0(15) . . ?
C92 C102 N42 120 . . ?
C92 C102 C152 123.0(16) . . ?
N42 C102 C152 115.5(15) . . ?
C102 N42 C112 120 . . ?
C102 N42 H5 120 . . ?
C112 N42 H5 120 . . ?
C122 C112 N42 120 . . ?
C122 C112 C162 120.0(16) . . ?
N42 C112 C162 119.7(16) . . ?
C112 C122 N32 120 . . ?
C112 C122 H12B 120 . . ?
N32 C122 H12B 120 . . ?
N32 C132 H13D 109.3 . . ?
N32 C132 H13E 109.1 . . ?
H13D C132 H13E 109.5 . . ?
N32 C132 H13F 110.1 . . ?
H13D C132 H13F 109.5 . . ?
H13E C132 H13F 109.5 . . ?
C92 C142 H14D 108.7 . . ?
C92 C142 H14E 108.8 . . ?
H14D C142 H14E 109.5 . . ?
C92 C142 H14F 110.9 . . ?
H14D C142 H14F 109.5 . . ?
H14E C142 H14F 109.5 . . ?
C102 C152 H15D 109.4 . . ?
C102 C152 H15E 109.8 . . ?
H15D C152 H15E 109.5 . . ?
C102 C152 H15F 109.2 . . ?
H15D C152 H15F 109.5 . . ?
H15E C152 H15F 109.5 . . ?
C112 C162 H16D 109.1 . . ?
C112 C162 H16E 109.6 . . ?
H16D C162 H16E 109.5 . . ?
C112 C162 H16F 109.7 . . ?
H16D C162 H16F 109.5 . . ?
H16E C162 H16F 109.5 . . ?
C17 N5 C20 120 . . ?
C17 N5 C21 121.6(15) . . ?
C20 N5 C21 118.3(15) . . ?
C18 C17 N5 120 . . ?
C18 C17 C22 119.3(15) . . ?
N5 C17 C22 120.7(15) . . ?
N6 C18 C17 120 . . ?
N6 C18 C23 116.0(16) . . ?
C17 C18 C23 122.3(16) . . ?
C18 N6 C19 120 . . ?
C18 N6 H6 120 . . ?
C19 N6 H6 120 . . ?
N6 C19 C20 120 . . ?
N6 C19 C24 119.7(15) . . ?
C20 C19 C24 120.3(15) . . ?
C19 C20 N5 120 . . ?
C19 C20 H20A 120 . . ?
N5 C20 H20A 120 . . ?
N5 C21 H21A 108.8 . . ?
N5 C21 H21B 110.4 . . ?
H21A C21 H21B 109.5 . . ?
N5 C21 H21C 109.3 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.7 . . ?
C17 C22 H22B 109.2 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 108.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 110.3 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.2 . . ?
C19 C24 H24B 109.4 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.7 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C172 N52 C202 120 . . ?
C172 N52 C212 121.2(16) . . ?
C202 N52 C212 118.8(16) . . ?
C182 C172 N52 120 . . ?
C182 C172 C222 118.1(15) . . ?
N52 C172 C222 121.3(16) . . ?
N62 C182 C172 120 . . ?
N62 C182 C232 115.8(17) . . ?
C172 C182 C232 121.9(16) . . ?
C182 N62 C192 120 . . ?
C182 N62 H7 120 . . ?
C192 N62 H7 120 . . ?
C202 C192 N62 120 . . ?
C202 C192 C242 121.1(16) . . ?
N62 C192 C242 118.3(16) . . ?
C192 C202 N52 120 . . ?
C192 C202 H20B 120 . . ?
N52 C202 H20B 120 . . ?
N52 C212 H21D 108.1 . . ?
N52 C212 H21E 111 . . ?
H21D C212 H21E 109.5 . . ?
N52 C212 H21F 109.2 . . ?
H21D C212 H21F 109.5 . . ?
H21E C212 H21F 109.5 . . ?
C172 C222 H22D 109.3 . . ?
C172 C222 H22E 108.9 . . ?
H22D C222 H22E 109.5 . . ?
C172 C222 H22F 110.2 . . ?
H22D C222 H22F 109.5 . . ?
H22E C222 H22F 109.5 . . ?
C182 C232 H23D 109.7 . . ?
C182 C232 H23E 108.5 . . ?
H23D C232 H23E 109.5 . . ?
C182 C232 H23F 110.2 . . ?
H23D C232 H23F 109.5 . . ?
H23E C232 H23F 109.5 . . ?
C192 C242 H24D 109.3 . . ?
C192 C242 H24E 110 . . ?
H24D C242 H24E 109.5 . . ?
C192 C242 H24F 109.2 . . ?
H24D C242 H24F 109.5 . . ?
H24E C242 H24F 109.5 . . ?

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
O1 H1 Br4 0.97 2.25 3.21(2) 178 2_565
O1 H2 Br9 0.9 2.35 3.25(2) 179.9 .
N2 H3 O1 0.88 1.63 2.50(2) 169.8 .
N4 H4 Br10 0.88 2.91 3.74(2) 157.3 2_664
C12 H12A Br9 0.95 2.37 3.26(2) 155.9 1_645
N42 H5 Br9 0.88 2.78 3.62(3) 160.1 1_645
N42 H5 Br11 0.88 3.13 3.61(4) 116.2 1_645
C122 H12B Br10 0.95 2.49 3.35(3) 150.4 2_664
C122 H12B Br11 0.95 2.99 3.53(4) 117.4 2_664
N6 H6 Br9 0.88 2.84 3.69(3) 162.3 1_655
C20 H20A Br8 0.95 2.72 3.35(5) 124.3 .
C20 H20A Br12 0.95 2.41 3.13(4) 132.4 .
N62 H7 Br8 0.88 2.88 3.42(4) 120.6 .
N62 H7 Br12 0.88 2.42 3.10(4) 134.6 .
C202 H20B Br9 0.95 2.8 3.69(2) 157.2 1_655

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1900243'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2017-11-08T23:14:12-00:00
_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         'Bi2 I9, 3(C5 H7 N2)'
_chemical_formula_sum            'C15 H21 Bi2 I9 N6'
_chemical_formula_weight         1845.44
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   28.8902(5)
_cell_length_b                   9.5425(2)
_cell_length_c                   13.4798(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3716.17(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12084
_cell_measurement_theta_min      1.954
_cell_measurement_theta_max      31.367

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

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    3.298
_exptl_crystal_F_000             3184

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

_exptl_absorpt_coefficient_mu    14.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.61732
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   synchrotron
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.67522
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0159765
_diffrn_orient_matrix_ub_12      0.0178681
_diffrn_orient_matrix_ub_13      -0.0343022
_diffrn_orient_matrix_ub_21      -0.0170305
_diffrn_orient_matrix_ub_22      0.0123734
_diffrn_orient_matrix_ub_23      -0.033164
_diffrn_orient_matrix_ub_31      -0.0010829
_diffrn_orient_matrix_ub_32      0.0673447
_diffrn_orient_matrix_ub_33      0.0152068
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_number            34170
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.963
_diffrn_reflns_theta_max         32.68
_diffrn_reflns_theta_full        23.899
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.78
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.78
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.777
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.775
_reflns_Friedel_coverage         0.926
_reflns_number_total             12387
_reflns_number_gt                10718
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   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] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12387
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 4389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(4)
_refine_diff_density_max         1.331
_refine_diff_density_min         -2.338
_refine_diff_density_rms         0.265

#----------------------------------------------------------------------------#
#                   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 0.003 0.0015 '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 0.0058 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.5193 1.6814 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -3.0941 9.8516 '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 0.31592(2) 0.14067(5) 0.20000(3) 0.02264(9) Uani 1 1 d . . . . .
Bi2 Bi 0.44696(2) 0.20371(5) 0.32345(3) 0.02262(9) Uani 1 1 d . . . . .
I1 I 0.41924(3) 0.15080(9) 0.09377(6) 0.02594(17) Uani 1 1 d . . . . .
I2 I 0.36824(3) -0.02727(9) 0.37148(6) 0.02524(16) Uani 1 1 d . . . . .
I3 I 0.35994(3) 0.41744(9) 0.31674(6) 0.02665(16) Uani 1 1 d . . . . .
I4 I 0.23590(3) 0.14344(10) 0.33080(7) 0.03196(19) Uani 1 1 d . . . . .
I5 I 0.29408(3) -0.11940(12) 0.09506(9) 0.0400(2) Uani 1 1 d . . . . .
I6 I 0.27346(4) 0.31635(12) 0.04283(7) 0.0395(2) Uani 1 1 d . . . . .
I7 I 0.46238(3) 0.25770(10) 0.53595(6) 0.02849(17) Uani 1 1 d . . . . .
I8 I 0.50950(3) 0.42811(10) 0.25167(6) 0.02857(17) Uani 1 1 d . . . . .
I9 I 0.51719(3) -0.02163(9) 0.32175(7) 0.03051(17) Uani 1 1 d . . . . .
N1 N 0.7006(5) 0.8456(14) 0.2201(10) 0.039(3) Uani 1 1 d . . . . .
N2 N 0.6557(4) 0.6452(12) 0.1164(9) 0.031(3) Uani 1 1 d . . . . .
N3 N 0.5697(4) 1.2760(12) 0.0323(8) 0.029(2) Uani 1 1 d . . . . .
N4 N 0.6351(5) 1.1540(15) 0.1530(9) 0.039(3) Uani 1 1 d . . . . .
N5 N 0.5900(4) 0.3149(11) 0.5707(7) 0.022(2) Uani 1 1 d . . . . .
N6 N 0.6166(4) 0.4167(13) 0.3880(9) 0.033(3) Uani 1 1 d . . . . .
C1 C 0.6834(7) 0.740(2) 0.2698(11) 0.049(4) Uani 1 1 d . . . . .
H1A H 0.687334 0.731741 0.339539 0.058 Uiso 1 1 calc R U . . .
C2 C 0.6590(5) 0.6400(17) 0.2160(12) 0.041(4) Uani 1 1 d . . . . .
H2A H 0.644225 0.565654 0.250589 0.05 Uiso 1 1 calc R U . . .
C3 C 0.6742(5) 0.7563(15) 0.0725(11) 0.034(3) Uani 1 1 d . . . . .
H3A H 0.670979 0.7652 0.002688 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6975(5) 0.8585(18) 0.1228(11) 0.036(3) Uani 1 1 d . . . . .
H4A H 0.710964 0.93582 0.089053 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7259(9) 0.954(2) 0.2794(15) 0.065(6) Uani 1 1 d . . . . .
H5A H 0.723202 1.045571 0.246418 0.098 Uiso 1 1 calc R U . . .
H5B H 0.758617 0.928471 0.284652 0.098 Uiso 1 1 calc R U . . .
H5C H 0.712367 0.960312 0.34598 0.098 Uiso 1 1 calc R U . . .
C6 C 0.5630(5) 1.1469(14) 0.0681(10) 0.027(3) Uani 1 1 d . . . . .
H6A H 0.535661 1.096655 0.051375 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5953(6) 1.0874(14) 0.1287(10) 0.032(3) Uani 1 1 d . . . . .
H7A H 0.589807 0.99633 0.154528 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6400(6) 1.2810(18) 0.1150(11) 0.040(4) Uani 1 1 d . . . . .
H8A H 0.667719 1.330369 0.130026 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6085(5) 1.3461(15) 0.0561(11) 0.032(3) Uani 1 1 d . . . . .
H9A H 0.613699 1.43845 0.03232 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5356(5) 1.3448(16) -0.0321(11) 0.035(3) Uani 1 1 d . . . . .
H10A H 0.550187 1.423926 -0.066244 0.052 Uiso 1 1 calc R U . . .
H10B H 0.509698 1.378854 0.008229 0.052 Uiso 1 1 calc R U . . .
H10C H 0.52412 1.277453 -0.081137 0.052 Uiso 1 1 calc R U . . .
C11 C 0.5942(5) 0.2290(18) 0.4942(11) 0.034(3) Uani 1 1 d . . . . .
H11A H 0.587324 0.132111 0.501055 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6091(5) 0.2831(15) 0.4030(10) 0.032(3) Uani 1 1 d . . . . .
H12A H 0.613843 0.219839 0.349573 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6107(6) 0.4986(15) 0.4666(11) 0.033(3) Uani 1 1 d . . . . .
H13A H 0.616591 0.595959 0.458956 0.04 Uiso 1 1 calc R U . . .
C14 C 0.5968(6) 0.4530(17) 0.5567(11) 0.037(3) Uani 1 1 d . . . . .
H14A H 0.591855 0.517407 0.609378 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5775(5) 0.2610(16) 0.6681(10) 0.029(3) Uani 1 1 d . . . . .
H15A H 0.558182 0.329866 0.7027 0.043 Uiso 1 1 calc R U . . .
H15B H 0.605637 0.243544 0.706729 0.043 Uiso 1 1 calc R U . . .
H15C H 0.56021 0.173244 0.66048 0.043 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 2.9076(9) . ?
Bi1 I5 2.9255(11) . ?
Bi1 I6 2.9672(10) . ?
Bi1 I2 3.1931(9) . ?
Bi1 I1 3.3120(9) . ?
Bi1 I3 3.3269(10) . ?
Bi2 I7 2.9443(9) . ?
Bi2 I9 2.9566(10) . ?
Bi2 I8 2.9640(10) . ?
Bi2 I2 3.2325(9) . ?
Bi2 I1 3.2376(9) . ?
Bi2 I3 3.2386(9) . ?
N1 C1 1.31(2) . ?
N1 C4 1.320(19) . ?
N1 C5 1.50(2) . ?
N2 C3 1.326(19) . ?
N2 C2 1.35(2) . ?
N3 C6 1.338(18) . ?
N3 C9 1.342(19) . ?
N3 C10 1.47(2) . ?
N4 C8 1.32(2) . ?
N4 C7 1.35(2) . ?
N5 C11 1.323(18) . ?
N5 C14 1.35(2) . ?
N5 C15 1.456(17) . ?
N6 C12 1.31(2) . ?
N6 C13 1.328(18) . ?
C1 C2 1.39(2) . ?
C1 H1A 0.95 . ?
C2 H2A 0.95 . ?
C3 C4 1.37(2) . ?
C3 H3A 0.95 . ?
C4 H4A 0.95 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C7 1.37(2) . ?
C6 H6A 0.95 . ?
C7 H7A 0.95 . ?
C8 C9 1.36(2) . ?
C8 H8A 0.95 . ?
C9 H9A 0.95 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C12 1.40(2) . ?
C11 H11A 0.95 . ?
C12 H12A 0.95 . ?
C13 C14 1.35(2) . ?
C13 H13A 0.95 . ?
C14 H14A 0.95 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 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 I5 97.43(3) . . ?
I4 Bi1 I6 95.69(3) . . ?
I5 Bi1 I6 92.57(4) . . ?
I4 Bi1 I2 86.68(3) . . ?
I5 Bi1 I2 91.51(3) . . ?
I6 Bi1 I2 174.98(3) . . ?
I4 Bi1 I1 168.10(3) . . ?
I5 Bi1 I1 90.58(3) . . ?
I6 Bi1 I1 92.72(3) . . ?
I2 Bi1 I1 84.32(2) . . ?
I4 Bi1 I3 90.57(3) . . ?
I5 Bi1 I3 169.93(3) . . ?
I6 Bi1 I3 92.71(3) . . ?
I2 Bi1 I3 82.83(2) . . ?
I1 Bi1 I3 80.61(2) . . ?
I7 Bi2 I9 91.78(3) . . ?
I7 Bi2 I8 95.68(3) . . ?
I9 Bi2 I8 96.00(3) . . ?
I7 Bi2 I2 91.77(3) . . ?
I9 Bi2 I2 89.34(3) . . ?
I8 Bi2 I2 170.68(3) . . ?
I7 Bi2 I1 174.31(3) . . ?
I9 Bi2 I1 92.80(3) . . ?
I8 Bi2 I1 87.20(3) . . ?
I2 Bi2 I1 84.90(2) . . ?
I7 Bi2 I3 91.97(3) . . ?
I9 Bi2 I3 172.12(3) . . ?
I8 Bi2 I3 90.52(3) . . ?
I2 Bi2 I3 83.62(2) . . ?
I1 Bi2 I3 83.08(2) . . ?
Bi2 I1 Bi1 79.28(2) . . ?
Bi1 I2 Bi2 81.13(2) . . ?
Bi2 I3 Bi1 79.05(2) . . ?
C1 N1 C4 123.7(14) . . ?
C1 N1 C5 116.5(14) . . ?
C4 N1 C5 119.9(14) . . ?
C3 N2 C2 116.4(13) . . ?
C6 N3 C9 119.7(13) . . ?
C6 N3 C10 121.8(13) . . ?
C9 N3 C10 118.6(12) . . ?
C8 N4 C7 115.4(13) . . ?
C11 N5 C14 119.0(12) . . ?
C11 N5 C15 120.5(12) . . ?
C14 N5 C15 120.6(11) . . ?
C12 N6 C13 115.3(12) . . ?
N1 C1 C2 117.0(14) . . ?
N1 C1 H1A 121.5 . . ?
C2 C1 H1A 121.5 . . ?
N2 C2 C1 122.1(14) . . ?
N2 C2 H2A 119 . . ?
C1 C2 H2A 119 . . ?
N2 C3 C4 123.3(14) . . ?
N2 C3 H3A 118.4 . . ?
C4 C3 H3A 118.4 . . ?
N1 C4 C3 117.3(15) . . ?
N1 C4 H4A 121.3 . . ?
C3 C4 H4A 121.3 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 119.9(13) . . ?
N3 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
N4 C7 C6 122.1(13) . . ?
N4 C7 H7A 119 . . ?
C6 C7 H7A 119 . . ?
N4 C8 C9 124.8(15) . . ?
N4 C8 H8A 117.6 . . ?
C9 C8 H8A 117.6 . . ?
N3 C9 C8 118.1(14) . . ?
N3 C9 H9A 120.9 . . ?
C8 C9 H9A 120.9 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 C12 118.9(14) . . ?
N5 C11 H11A 120.5 . . ?
C12 C11 H11A 120.5 . . ?
N6 C12 C11 123.1(14) . . ?
N6 C12 H12A 118.4 . . ?
C11 C12 H12A 118.4 . . ?
N6 C13 C14 124.5(13) . . ?
N6 C13 H13A 117.8 . . ?
C14 C13 H13A 117.8 . . ?
N5 C14 C13 119.0(13) . . ?
N5 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 I6 0.95 3 3.923(15) 164.1 2_665
C2 H2A N6 0.95 2.47 3.378(19) 160.7 .
C3 H3A I2 0.95 3.27 3.941(14) 129.7 2_664
C3 H3A I3 0.95 3.18 3.951(14) 139.4 2_664
C4 H4A I6 0.95 3.04 3.950(16) 161 3_565
C5 H5A I4 0.98 3.2 3.91(2) 130.7 3_565
C5 H5B I3 0.98 3.3 4.09(2) 138.7 3_565
C7 H7A I7 0.95 3.27 3.897(15) 125.2 2_664
C7 H7A I9 0.95 3.08 3.599(14) 115.7 1_565
C9 H9A I3 0.95 3.3 4.041(14) 136 2_674
C9 H9A N2 0.95 2.58 3.266(18) 129.6 1_565
C10 H10A I8 0.98 3.32 3.859(16) 116.9 2_674
C10 H10B I8 0.98 3.31 3.978(15) 126.7 1_565
C10 H10C I9 0.98 3.02 3.965(14) 163.2 2_664
C11 H11A I1 0.95 2.98 3.884(17) 159.2 2_655
C13 H13A I1 0.95 3.2 3.857(15) 128.3 2_665
C14 H14A I1 0.95 3.19 3.842(16) 127.5 2_665
C14 H14A I3 0.95 3.18 3.922(15) 135.8 2_665
C15 H15A I8 0.98 3.1 4.048(14) 163.9 2_665
C15 H15B I2 0.98 3.12 3.866(14) 133.6 2_655
C15 H15C I1 0.98 3.27 4.056(15) 138 2_655

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1900237'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2018-04-13T14:57:44-00:00
_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         'Bi Br6, 2(C4 H5 N2), H3 O, H2 O'
_chemical_formula_sum            'C8 H15 Bi Br6 N4 O2'
_chemical_formula_weight         887.68

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9423(6)
_cell_length_b                   9.2461(6)
_cell_length_c                   14.0873(8)
_cell_angle_alpha                77.477(2)
_cell_angle_beta                 86.384(2)
_cell_angle_gamma                65.451(2)
_cell_volume                     1033.79(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5081
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      29.97
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          .14
_exptl_crystal_size_mid          .20
_exptl_crystal_size_max          .24
_exptl_crystal_density_diffrn    2.852
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

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

_exptl_absorpt_coefficient_mu    20.129
_exptl_absorpt_process_details   TWINABS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.0299
_exptl_absorpt_correction_T_min  0.0060

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

_diffrn_ambient_temperature      120(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_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_number            27294
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         25.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3806
_reflns_number_gt                3528
_reflns_threshold_expression     'I > 2σ(I)'

_twin_special_details            
;
To collect experimental data for 5, the spliced crystals have been 
investigated. The main domain made up ∼ 70% of the volume and the latter 
part contained more than 5 domains thus not allowing one to take absorbance 
into account correctly.


 TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
 ------------------------------------------------------------------

 Equivalent reflections defined according to point group -1    

 Reading batch  1 from file 11_24_4_01.mul
 Reading batch  2 from file 11_24_4_02.mul
 Reading batch  3 from file 11_24_4_03.mul
 Reading batch  4 from file 11_24_4_04.mul

  2 twin components present

 Mean and maximum errors in direction cosine check function =   0.001   0.009
 The mean error should not exceed 0.008, and is usually caused by matrix
 changes during data processing.

 Maximum 2-theta =  55.35 deg.   Approximate wavelength = 0.71069 Angstroms
 Approximate highest resolution = 0.765 Angstroms
 Approximate unit-cell:   8.937   9.240  14.081   77.49   86.35   65.46

 ==============================================================================

 PART 1 - Refinement of parameters to model systematic errors

    10199 data (   3556 unique ) involve domain  1 only,  mean I/sigma   8.8
    10178 data (   3546 unique ) involve domain  2 only,  mean I/sigma   6.5
     7029 data (   2526 unique ) involve   2 domains,  mean I/sigma  10.1

 Settings for parameter refinement:

 Maximum resolution =  0.1000 A
 (Intensity/sigma) threshold = 3.000
 Restraint esd for equal adjacent scale factors =  0.0050
 Maximum odd and even orders for spherical harmonics =   3   6


 Parameter refinement for twin component  1
 ------------------------------------------

    7136 single and      0 composite reflections used for parameter fitting
 Effective data to parameter ratio =    3.37

 wR2(int) =  0.0872 (selected reflections only, before parameter refinement)

 Cycle wR2(incid) wR2(diffr) Mean wt.
    1    0.0636    0.0511    0.9495
    2    0.0469    0.0452    0.9570
    3    0.0444    0.0439    0.9579
    4    0.0436    0.0434    0.9581
    5    0.0433    0.0432    0.9582
    6    0.0431    0.0431    0.9583
    7    0.0430    0.0430    0.9583
    8    0.0430    0.0430    0.9583
    9    0.0429    0.0429    0.9583
   10    0.0429    0.0429    0.9583
   11    0.0429    0.0429    0.9583
   12    0.0428    0.0429    0.9583
   13    0.0428    0.0428    0.9583
   14    0.0428    0.0428    0.9584
   15    0.0428    0.0428    0.9584
   16    0.0428    0.0428    0.9584
   17    0.0428    0.0428    0.9584
   18    0.0428    0.0428    0.9584
   19    0.0428    0.0428    0.9584
   20    0.0428    0.0428    0.9584
   21    0.0428    0.0428    0.9584
   22    0.0428    0.0428    0.9584
   23    0.0428    0.0428    0.9584
   24    0.0427    0.0428    0.9584
   25    0.0427    0.0428    0.9584
   26    0.0427    0.0428    0.9584
   27    0.0427    0.0428    0.9584
   28    0.0427    0.0427    0.9584
   29    0.0427    0.0427    0.9584
   30    0.0427    0.0427    0.9584
   31    0.0427    0.0427    0.9585
   32    0.0427    0.0427    0.9585
   33    0.0427    0.0427    0.9585
   34    0.0427    0.0427    0.9585
   35    0.0427    0.0427    0.9585
   36    0.0427    0.0427    0.9585
   37    0.0427    0.0427    0.9585
   38    0.0427    0.0427    0.9585
   39    0.0427    0.0427    0.9585
   40    0.0427    0.0427    0.9585

 wR2(int) =  0.0427 (selected reflections only, after parameter refinement)


 Parameter refinement for twin component  2
 ------------------------------------------

    6374 single and      0 composite reflections used for parameter fitting
 Effective data to parameter ratio =    3.02

 wR2(int) =  0.0953 (selected reflections only, before parameter refinement)

 Cycle wR2(incid) wR2(diffr) Mean wt.
    1    0.0707    0.0578    0.9345
    2    0.0533    0.0516    0.9424
    3    0.0507    0.0502    0.9433
    4    0.0498    0.0496    0.9437
    5    0.0493    0.0492    0.9439
    6    0.0491    0.0490    0.9442
    7    0.0489    0.0488    0.9444
    8    0.0488    0.0487    0.9445
    9    0.0486    0.0486    0.9447
   10    0.0486    0.0486    0.9448
   11    0.0485    0.0485    0.9450
   12    0.0485    0.0484    0.9451
   13    0.0484    0.0484    0.9452
   14    0.0484    0.0484    0.9453
   15    0.0483    0.0483    0.9453
   16    0.0483    0.0483    0.9454
   17    0.0483    0.0483    0.9455
   18    0.0483    0.0483    0.9455
   19    0.0482    0.0482    0.9456
   20    0.0482    0.0482    0.9456
   21    0.0482    0.0482    0.9457
   22    0.0482    0.0482    0.9457
   23    0.0482    0.0482    0.9457
   24    0.0481    0.0482    0.9458
   25    0.0481    0.0481    0.9458
   26    0.0481    0.0481    0.9458
   27    0.0481    0.0481    0.9458
   28    0.0481    0.0481    0.9458
   29    0.0481    0.0481    0.9459
   30    0.0481    0.0481    0.9459
   31    0.0480    0.0480    0.9459
   32    0.0480    0.0480    0.9459
   33    0.0480    0.0480    0.9459
   34    0.0480    0.0480    0.9459
   35    0.0480    0.0480    0.9459
   36    0.0480    0.0480    0.9459
   37    0.0480    0.0480    0.9459
   38    0.0480    0.0480    0.9460
   39    0.0480    0.0480    0.9460
   40    0.0480    0.0480    0.9460

 wR2(int) =  0.0480 (selected reflections only, after parameter refinement)

 ==============================================================================

 PART 2 - Reject outliers and establish error model

 Rejected reflections are ignored in the statistics and Postscript plots
 (except the detector diagnostics) and in the output .hkl files. All statistics
 and error estimates refer to total intensities (of single or composite
 reflections) only. Before applying rejections there are:

   27406 total and   9628 unique reflections assuming Friedel's law.

   27394 total and   9626 unique reflections after rejecting pathological cases 

   27306 total and   9624 unique reflections left after |I-|/su test


 g = 0.0259 gave best error model; g set to 0.0259 for further calculations


 Statistics for singles of twin component  1
 -------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1  -22.5  0.0367   0.852 - 1.142   0.943 - 1.138   0.765    2903    2448
    2  -22.5  0.0420   0.963 - 1.238   0.953 - 1.144   0.848    2834    2359
    3  -22.5  0.0453   0.683 - 0.966   0.943 - 1.144   0.786    2281    1892
    4  -22.5  0.0435   0.699 - 1.008   0.943 - 1.144   0.752    2168    1798

   All scans  0.0417   0.683 - 1.238   0.943 - 1.144   0.788   10186    8497


 Statistics for singles of twin component  2
 -------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1  -22.5  0.0505   0.848 - 1.160   0.926 - 1.206   0.765    2887    2309
    2  -22.5  0.0532   0.905 - 1.170   0.927 - 1.203   0.848    2820    2182
    3  -22.5  0.0616   0.607 - 0.979   0.915 - 1.193   0.786    2293    1810
    4  -22.5  0.0583   0.661 - 0.996   0.915 - 1.192   0.752    2165    1714

   All scans  0.0556   0.607 - 1.170   0.915 - 1.206   0.788   10165    8015


 Statistics for all composite reflections
 ----------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1  -22.5  0.0502   0.852 - 1.135   0.930 - 1.145   0.765    1668    1544
    2  -22.5  0.0522   0.921 - 1.224   0.949 - 1.149   0.848    1567    1432
    3  -22.5  0.0593   0.642 - 0.976   0.925 - 1.105   0.786    1904    1686
    4  -22.5  0.0576   0.680 - 1.002   0.925 - 1.115   0.752    1816    1619

   All scans  0.0550   0.642 - 1.224   0.925 - 1.149   0.788    6955    6281


 Statistics for all single and composite reflections
 ---------------------------------------------------

 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1  -22.5  0.0451   0.848 - 1.160   0.926 - 1.206   0.765    7458    6301
    2  -22.5  0.0485   0.905 - 1.238   0.927 - 1.203   0.848    7221    5973
    3  -22.5  0.0549   0.607 - 0.979   0.915 - 1.193   0.786    6478    5388
    4  -22.5  0.0529   0.661 - 1.008   0.915 - 1.192   0.752    6149    5131

   All scans  0.0502   0.607 - 1.238   0.915 - 1.206   0.788   27306   22793

 su = K * Sqrt[ sigma^2(I) + (g)^2 ]  where sigma(I) is estimated by SAINT

 The above statistics are based on all non-rejected data, ignoring
 reflections without equivalents when estimating R(int) and K.

 ==============================================================================

 PART 3 - Output Postscript diagnostics and corrected data


 Unique HKLF 4 data extracted from all observed data

 Cycle   N(1) Rint(1)  N(all) Rint(all) Twin fractions
    1   17100  0.0866   27233  0.0891   0.6248  0.3752
    2   17129  0.0771   27294  0.0772   0.6228  0.3772
    3   17129  0.0577   27294  0.0610   0.6235  0.3765
    4   17129  0.0574   27294  0.0608   0.6235  0.3765
    5   17129  0.0573   27294  0.0607   0.6235  0.3765
    6   17129  0.0572   27294  0.0606   0.6235  0.3765
    7   17129  0.0571   27294  0.0606   0.6235  0.3765
    8   17129  0.0570   27294  0.0605   0.6235  0.3765
    9   17129  0.0570   27294  0.0605   0.6235  0.3765
   10   17129  0.0569   27294  0.0604   0.6234  0.3766
   11   17129  0.0569   27294  0.0604   0.6234  0.3766
   12   17129  0.0569   27294  0.0604   0.6234  0.3766
   13   17129  0.0568   27294  0.0604   0.6234  0.3766
   14   17129  0.0568   27294  0.0604   0.6234  0.3766
   15   17129  0.0568   27294  0.0603   0.6234  0.3766
   16   17129  0.0568   27294  0.0603   0.6234  0.3766
   17   17129  0.0568   27294  0.0603   0.6234  0.3766
   18   17129  0.0568   27294  0.0603   0.6234  0.3766
   19   17129  0.0568   27294  0.0603   0.6234  0.3766
   20   17129  0.0568   27294  0.0603   0.6234  0.3766

 N(1) and Rint(1) refer to singles and composites that include domain 1.

 Rint = 0.0603  for all   27294  observations and
 Rint = 0.0480  for all   16729  observations with I > 3sigma(I)

 Rint is based on agreement between observed single and composite intensities
 and those calculated from refined unique intensities and twin fractions.

    4027 Corrected reflections written to file twin4.hkl
 Reflections merged according to point-group -1    
 Minimum and maximum apparent transmission:  0.005917  0.029912
 Additional spherical absorption correction applied with mu*r =  4.0000


 HKLF 5 dataset constructed from all observations involving domain 1
    5100 Corrected reflections written to file twin5.hkl
 Reflections merged according to point-group -1    
 Single reflections that also occur in composites omitted
 Minimum and maximum apparent transmission:  0.006201  0.029912
 Additional spherical absorption correction applied with mu*r =  4.0000



;

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          'Refined as a 2-component perfect twin.,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)+(0.0500P)²+20.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3806
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.043
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         3.879
_refine_diff_density_min         -0.986
_refine_diff_density_rms         0.264

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.5 0.02318(16) Uani 1 2 d S . P . .
Bi2 Bi 0.5 0 0 0.02351(16) Uani 1 2 d S . P . .
Br1 Br 0.14766(14) -0.20584(13) 0.36728(8) 0.0311(3) Uani 1 1 d . . . . .
Br2 Br 0.18415(14) 0.18452(13) 0.42047(8) 0.0290(3) Uani 1 1 d . . . . .
Br3 Br -0.27201(14) 0.20196(15) 0.36778(8) 0.0340(3) Uani 1 1 d . . . . .
Br4 Br 0.44036(15) 0.20006(15) 0.13848(9) 0.0345(3) Uani 1 1 d . . . . .
Br5 Br 0.41962(17) -0.23642(15) 0.13080(10) 0.0425(3) Uani 1 1 d . . . . .
Br6 Br 0.83651(13) -0.15982(13) 0.06276(8) 0.0280(2) Uani 1 1 d . . . . .
O1 O 0.0664(9) 0.5391(9) 0.2359(6) 0.0317(18) Uani 1 1 d . . . . .
H1 H -0.016528 0.604889 0.277823 0.038 Uiso 1 1 d R U . . .
H2 H 0.041652 0.477469 0.210751 0.038 Uiso 1 1 d R U . . .
H3 H 0.156573 0.50784 0.249371 0.038 Uiso 1 1 d R U . . .
O2 O 0.3616(10) 0.4643(10) 0.2850(6) 0.0324(18) Uani 1 1 d . . . . .
H4 H 0.360347 0.567589 0.250049 0.039 Uiso 1 1 d R U . . .
H5 H 0.466156 0.396398 0.274579 0.039 Uiso 1 1 d R U . . .
N1 N 0.8132(12) -0.3491(12) 0.3481(7) 0.032(2) Uani 1 1 d . . . . .
N2 N 0.5304(12) -0.2277(13) 0.4418(8) 0.036(2) Uani 1 1 d . . . . .
H6 H 0.436915 -0.18888 0.471553 0.043 Uiso 1 1 calc R U . . .
N3 N 0.9757(12) 0.3504(13) 0.1594(8) 0.036(2) Uani 1 1 d . . . . .
N4 N 0.8382(13) 0.1800(13) 0.0919(8) 0.040(3) Uani 1 1 d . . . . .
H7 H 0.793748 0.124353 0.069901 0.047 Uiso 1 1 calc R U . . .
C1 C 0.7806(16) -0.4376(15) 0.4265(9) 0.036(3) Uani 1 1 d . . . . .
H1A H 0.858557 -0.54614 0.449073 0.043 Uiso 1 1 calc R U . . .
C2 C 0.6386(16) -0.3793(15) 0.4770(9) 0.035(3) Uani 1 1 d . . . . .
H2A H 0.618541 -0.444112 0.534184 0.042 Uiso 1 1 calc R U . . .
C3 C 0.5576(16) -0.1338(16) 0.3646(9) 0.038(3) Uani 1 1 d . . . . .
H3A H 0.478195 -0.026191 0.341298 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7022(15) -0.1944(15) 0.3190(9) 0.036(3) Uani 1 1 d . . . . .
H4A H 0.725627 -0.125953 0.265116 0.044 Uiso 1 1 calc R U . . .
C5 C 1.0363(15) 0.1890(16) 0.1843(9) 0.036(3) Uani 1 1 d . . . . .
H5A H 1.129495 0.133554 0.227603 0.044 Uiso 1 1 calc R U . . .
C6 C 0.9711(15) 0.0998(16) 0.1508(9) 0.035(3) Uani 1 1 d . . . . .
H6A H 1.018637 -0.015616 0.168617 0.042 Uiso 1 1 calc R U . . .
C7 C 0.7709(16) 0.3403(16) 0.0655(12) 0.047(3) Uani 1 1 d . . . . .
H7A H 0.674567 0.395178 0.024768 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8442(16) 0.4264(16) 0.0987(12) 0.047(3) Uani 1 1 d . . . . .
H8A H 0.800432 0.541361 0.078038 0.057 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 Br1 2.8293(11) . ?
Bi1 Br1 2.8293(11) 2_556 ?
Bi1 Br2 2.8550(11) . ?
Bi1 Br2 2.8550(11) 2_556 ?
Bi1 Br3 2.8569(11) 2_556 ?
Bi1 Br3 2.8569(11) . ?
Bi2 Br5 2.8428(12) 2_655 ?
Bi2 Br5 2.8429(12) . ?
Bi2 Br6 2.8450(11) 2_655 ?
Bi2 Br6 2.8451(11) . ?
Bi2 Br4 2.8505(11) 2_655 ?
Bi2 Br4 2.8506(11) . ?
O1 H1 0.9971 . ?
O1 H2 0.8372 . ?
O1 H3 0.7563 . ?
O2 H4 0.9711 . ?
O2 H5 0.9079 . ?
N1 C1 1.319(15) . ?
N1 C4 1.347(16) . ?
N2 C3 1.315(17) . ?
N2 C2 1.334(16) . ?
N2 H6 0.88 . ?
N3 C5 1.330(16) . ?
N3 C8 1.336(18) . ?
N4 C7 1.321(17) . ?
N4 C6 1.332(17) . ?
N4 H7 0.88 . ?
C1 C2 1.375(18) . ?
C1 H1A 0.95 . ?
C2 H2A 0.95 . ?
C3 C4 1.360(18) . ?
C3 H3A 0.95 . ?
C4 H4A 0.95 . ?
C5 C6 1.359(18) . ?
C5 H5A 0.95 . ?
C6 H6A 0.95 . ?
C7 C8 1.384(19) . ?
C7 H7A 0.95 . ?
C8 H8A 0.95 . ?

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
Br1 Bi1 Br1 180.00(5) . 2_556 ?
Br1 Bi1 Br2 89.01(3) . . ?
Br1 Bi1 Br2 90.99(3) 2_556 . ?
Br1 Bi1 Br2 90.99(3) . 2_556 ?
Br1 Bi1 Br2 89.01(3) 2_556 2_556 ?
Br2 Bi1 Br2 180 . 2_556 ?
Br1 Bi1 Br3 88.64(3) . 2_556 ?
Br1 Bi1 Br3 91.36(3) 2_556 2_556 ?
Br2 Bi1 Br3 87.59(3) . 2_556 ?
Br2 Bi1 Br3 92.41(3) 2_556 2_556 ?
Br1 Bi1 Br3 91.36(3) . . ?
Br1 Bi1 Br3 88.64(3) 2_556 . ?
Br2 Bi1 Br3 92.41(3) . . ?
Br2 Bi1 Br3 87.59(3) 2_556 . ?
Br3 Bi1 Br3 180.00(4) 2_556 . ?
Br5 Bi2 Br5 180 2_655 . ?
Br5 Bi2 Br6 92.09(4) 2_655 2_655 ?
Br5 Bi2 Br6 87.91(4) . 2_655 ?
Br5 Bi2 Br6 87.91(4) 2_655 . ?
Br5 Bi2 Br6 92.09(4) . . ?
Br6 Bi2 Br6 180 2_655 . ?
Br5 Bi2 Br4 93.32(4) 2_655 2_655 ?
Br5 Bi2 Br4 86.68(4) . 2_655 ?
Br6 Bi2 Br4 89.32(3) 2_655 2_655 ?
Br6 Bi2 Br4 90.68(3) . 2_655 ?
Br5 Bi2 Br4 86.68(4) 2_655 . ?
Br5 Bi2 Br4 93.32(4) . . ?
Br6 Bi2 Br4 90.68(3) 2_655 . ?
Br6 Bi2 Br4 89.32(3) . . ?
Br4 Bi2 Br4 180 2_655 . ?
H1 O1 H2 117.4 . . ?
H1 O1 H3 118.5 . . ?
H2 O1 H3 115 . . ?
H4 O2 H5 100.2 . . ?
C1 N1 C4 117.3(11) . . ?
C3 N2 C2 122.7(11) . . ?
C3 N2 H6 118.6 . . ?
C2 N2 H6 118.6 . . ?
C5 N3 C8 117.6(11) . . ?
C7 N4 C6 122.2(11) . . ?
C7 N4 H7 118.9 . . ?
C6 N4 H7 118.9 . . ?
N1 C1 C2 122.8(11) . . ?
N1 C1 H1A 118.6 . . ?
C2 C1 H1A 118.6 . . ?
N2 C2 C1 116.9(11) . . ?
N2 C2 H2A 121.5 . . ?
C1 C2 H2A 121.5 . . ?
N2 C3 C4 118.4(12) . . ?
N2 C3 H3A 120.8 . . ?
C4 C3 H3A 120.8 . . ?
N1 C4 C3 121.8(12) . . ?
N1 C4 H4A 119.1 . . ?
C3 C4 H4A 119.1 . . ?
N3 C5 C6 123.1(12) . . ?
N3 C5 H5A 118.5 . . ?
C6 C5 H5A 118.5 . . ?
N4 C6 C5 117.6(12) . . ?
N4 C6 H6A 121.2 . . ?
C5 C6 H6A 121.2 . . ?
N4 C7 C8 118.4(12) . . ?
N4 C7 H7A 120.8 . . ?
C8 C7 H7A 120.8 . . ?
N3 C8 C7 121.1(12) . . ?
N3 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 N1 1 1.71 2.647(12) 154.3 1_465 yes
O1 H2 N3 0.84 1.8 2.639(13) 176.4 1_455 yes
O1 H3 O2 0.76 1.79 2.536(11) 171.2 . yes
O2 H4 Br5 0.97 2.4 3.330(8) 160.7 1_565 yes
O2 H5 Br3 0.91 2.51 3.260(8) 140.1 1_655 yes
N2 H6 Br1 0.88 3.13 3.556(10) 112.2 . yes
N2 H6 Br3 0.88 2.63 3.410(10) 148.1 2_556 yes
N4 H7 Br4 0.88 3.08 3.512(10) 112.6 . yes
N4 H7 Br6 0.88 2.52 3.262(10) 142.9 . yes
C1 H1A Br1 0.95 3.08 3.748(12) 128.9 2_646 yes
C1 H1A Br2 0.95 3.02 3.854(13) 147.7 1_645 yes
C2 H2A Br1 0.95 3.09 3.737(12) 126.5 2_646 yes
C2 H2A O2 0.95 2.53 3.274(14) 135.8 2_656 yes
C3 H3A Br2 0.95 2.88 3.597(13) 133.6 . yes
C3 H3A Br4 0.95 3.1 3.774(13) 129.5 . yes
C4 H4A Br6 0.95 3 3.721(13) 134.1 . yes
C5 H5A Br2 0.95 2.96 3.642(13) 129.9 1_655 yes
C6 H6A Br1 0.95 2.97 3.598(12) 124.5 1_655 yes
C6 H6A Br6 0.95 3.1 3.554(13) 110.8 . yes
C8 H8A Br6 0.95 2.87 3.721(13) 149.1 1_565 yes

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1900242'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_date             2019-04-02T21:09:45-00:00
_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         'Bi2 Br5.16 I3.84, 3(C5 H7 N2)'
_chemical_formula_sum            'C15 H21 Bi2 Br5.16 I3.84 N6'
_chemical_formula_weight         1602.97

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.0541(6)
_cell_length_b                   12.8474(5)
_cell_length_c                   34.9720(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6763.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.8

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

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    3.148
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             5625

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

_exptl_absorpt_coefficient_mu    20.011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0015
_exptl_absorpt_correction_T_max  0.0195
_exptl_special_details           
;
   80247 Corrected reflections written to file 
C:\frames\Ilyukhin\01_14_1\work\01_14_1_0m.hkl
 Estimated minimum and maximum transmission:  0.0015  0.0195
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  5.0000
;

#----------------------------------------------------------------------------#
#                   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  0.095
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_number            75467
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.694
_diffrn_reflns_theta_max         26.424
_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_coverage         0
_reflns_number_total             6939
_reflns_number_gt                5286
_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-2018/1 (Sheldrick, 2018)'
_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)+(0.1000P)²+40.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6939
_refine_ls_number_parameters     325
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1739
_refine_ls_wR_factor_gt          0.151
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.511
_refine_diff_density_min         -1.371
_refine_diff_density_rms         0.283
_refine_special_details          
;
In the crystal structure of 10, eight of nine positions of X ligands in 
[Bi2X9]3- are statistical, and ratio of the corresponding occupancies, Br:I, 
varies from 0.30:0.70 to 0.82:0.18. These values were obtained via the 
isotropic refinement with Uiso = 0.03, and were set as constant in further 
calculations. The coordinates of Br and I atoms were refined independently, 
distances between the corresponding positions are in the 0.021-0.607 Å 
range. Cations are geometrically restricted (AFIX66 command). 
;

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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 0.54610(3) 0.35115(4) -0.17035(2) 0.04309(18) Uani 1 1 d . . . . .
Bi2 Bi 0.42128(4) 0.25174(4) -0.07439(2) 0.04647(18) Uani 1 1 d . . . . .
Br1 Br 0.5079(2) 0.1348(2) -0.13799(12) 0.0446(7) Uani 0.82 1 d . U P . .
Br2 Br 0.7175(6) 0.2716(7) -0.1939(2) 0.0302(17) Uani 0.4 1 d . U P . .
Br3 Br 0.4501(15) 0.2856(17) -0.2364(6) 0.040(2) Uani 0.35 1 d . U P . .
Br4 Br 0.5981(8) 0.5577(9) -0.1886(2) 0.081(4) Uani 0.45 1 d . U P . .
Br5 Br 0.3583(14) 0.4094(17) -0.1355(7) 0.145(7) Uani 0.3 1 d . U P . .
Br6 Br 0.59402(7) 0.39302(9) -0.08105(4) 0.0518(3) Uani 0.45 1 d . . P . .
Br7 Br 0.5043(5) 0.1156(5) -0.0279(2) 0.0681(14) Uani 0.8 1 d . U P . .
Br8 Br 0.2786(3) 0.1226(4) -0.08668(14) 0.0629(11) Uani 0.8 1 d . U P . .
Br9 Br 0.3301(9) 0.3547(10) -0.0159(5) 0.0544(18) Uani 0.79 1 d . U P . .
I1 I 0.5082(16) 0.1325(18) -0.1394(9) 0.127(7) Uani 0.18 1 d . U P . .
I2 I 0.7154(4) 0.2750(6) -0.19390(19) 0.0805(19) Uani 0.6 1 d . U P . .
I3 I 0.4590(6) 0.3038(6) -0.2432(2) 0.0468(10) Uani 0.65 1 d . U P . .
I4 I 0.5990(3) 0.5581(3) -0.18819(14) 0.0548(16) Uani 0.55 1 d . . P . .
I5 I 0.35677(12) 0.41193(15) -0.13726(7) 0.0412(4) Uani 0.7 1 d . U P . .
I6 I 0.59402(7) 0.39302(9) -0.08105(4) 0.0518(3) Uani 0.55 1 d . . P . .
I7 I 0.5191(17) 0.1361(17) -0.0192(6) 0.075(4) Uani 0.2 1 d . U P . .
I8 I 0.2872(10) 0.1112(11) -0.0702(4) 0.066(3) Uani 0.2 1 d . U P . .
I9 I 0.340(3) 0.370(3) -0.0107(13) 0.057(5) Uani 0.21 1 d . U P . .
N1 N 0.2927(6) -0.0335(5) 0.0895(3) 0.050(3) Uani 1 1 d G . . . .
C1 C 0.3162(6) 0.0153(7) 0.1235(2) 0.062(4) Uani 1 1 d G . . . .
H1A H 0.304703 -0.017754 0.14725 0.074 Uiso 1 1 calc R U . . .
C2 C 0.3567(7) 0.1126(7) 0.1227(3) 0.063(4) Uani 1 1 d G . . . .
H2A H 0.372762 0.145954 0.14588 0.076 Uiso 1 1 calc R U . . .
N2 N 0.3736(6) 0.1610(6) 0.0879(3) 0.068(4) Uani 1 1 d G . . . .
C3 C 0.3500(7) 0.1121(7) 0.0539(3) 0.063(4) Uani 1 1 d G . . . .
H3A H 0.361557 0.14517 0.030088 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3096(6) 0.0149(7) 0.0547(2) 0.062(4) Uani 1 1 d G . . . .
H4A H 0.293498 -0.018538 0.031457 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2510(13) -0.1337(11) 0.0907(6) 0.069(5) Uani 1 1 d . . . . .
H5A H 0.238705 -0.157453 0.064644 0.104 Uiso 1 1 calc R U . . .
H5B H 0.290652 -0.183497 0.103406 0.104 Uiso 1 1 calc R U . . .
H5C H 0.195204 -0.128837 0.105053 0.104 Uiso 1 1 calc R U . . .
N3 N 0.5680(6) 0.3039(7) 0.0666(3) 0.064(4) Uani 1 1 d G . . . .
C6 C 0.6066(7) 0.2066(8) 0.0615(3) 0.073(5) Uani 1 1 d G . . . .
H6A H 0.627452 0.186281 0.037018 0.088 Uiso 1 1 calc R U . . .
C7 C 0.6146(8) 0.1389(6) 0.0924(4) 0.078(6) Uani 1 1 d G . . . .
H7A H 0.640976 0.072389 0.088908 0.094 Uiso 1 1 calc R U . . .
N4 N 0.5841(8) 0.1686(7) 0.1283(3) 0.075(4) Uani 1 1 d G . . . .
C8 C 0.5455(7) 0.2659(8) 0.1333(3) 0.066(5) Uani 1 1 d G . . . .
H8A H 0.524653 0.286201 0.157859 0.08 Uiso 1 1 calc R U . . .
C9 C 0.5375(7) 0.3336(6) 0.1025(3) 0.060(4) Uani 1 1 d G . . . .
H9A H 0.511129 0.400095 0.105969 0.072 Uiso 1 1 calc R U . . .
C10 C 0.5636(14) 0.3767(17) 0.0356(7) 0.093(7) Uani 1 1 d . . . . .
H10A H 0.534462 0.440744 0.044248 0.14 Uiso 1 1 calc R U . . .
H10B H 0.623801 0.392928 0.02674 0.14 Uiso 1 1 calc R U . . .
H10C H 0.529421 0.34631 0.014485 0.14 Uiso 1 1 calc R U . . .
N5 N 0.7100(5) 0.5290(7) -0.2880(3) 0.056(3) Uani 1 1 d G . . . .
C11 C 0.7025(5) 0.6141(8) -0.3123(3) 0.068(5) Uani 1 1 d G . . . .
H11A H 0.650755 0.622558 -0.327537 0.081 Uiso 1 1 calc R U . . .
C12 C 0.7707(7) 0.6868(7) -0.3143(3) 0.074(5) Uani 1 1 d G . . . .
H12A H 0.765532 0.745032 -0.330947 0.089 Uiso 1 1 calc R U . . .
N6 N 0.8464(6) 0.6745(7) -0.2920(3) 0.065(4) Uani 1 1 d G . . . .
C13 C 0.8540(6) 0.5893(8) -0.2677(3) 0.069(5) Uani 1 1 d G . . . .
H13A H 0.905706 0.58085 -0.25251 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7858(7) 0.5166(7) -0.2657(3) 0.061(4) Uani 1 1 d G . . . .
H14A H 0.790929 0.458374 -0.2491 0.074 Uiso 1 1 calc R U . . .
C15 C 0.6376(13) 0.4522(16) -0.2868(6) 0.076(5) Uani 1 1 d . . . . .
H15A H 0.652501 0.397205 -0.268453 0.114 Uiso 1 1 calc R U . . .
H15B H 0.582545 0.486643 -0.27883 0.114 Uiso 1 1 calc R U . . .
H15C H 0.629592 0.421719 -0.312222 0.114 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 Br4 2.839(12) . ?
Bi1 I4 2.845(4) . ?
Bi1 I2 2.852(7) . ?
Bi1 Br3 2.85(3) . ?
Bi1 Br2 2.895(9) . ?
Bi1 I3 2.929(9) . ?
Bi1 Br1 3.056(3) . ?
Bi1 I1 3.06(2) . ?
Bi1 Br5 3.17(2) . ?
Bi1 I5 3.174(2) . ?
Bi1 I6 3.2500(14) . ?
Bi2 Br7 2.696(7) . ?
Bi2 I8 2.712(14) . ?
Bi2 Br8 2.748(5) . ?
Bi2 Br9 2.796(15) . ?
Bi2 I7 2.84(2) . ?
Bi2 I9 2.96(4) . ?
Bi2 Br1 2.984(4) . ?
Bi2 I1 3.04(3) . ?
Bi2 Br5 3.09(2) . ?
Bi2 I5 3.164(2) . ?
Bi2 I6 3.1798(12) . ?
Br8 I8 0.607(12) . ?
N1 C1 1.39 . ?
N1 C4 1.39 . ?
N1 C5 1.433(16) . ?
C1 C2 1.39 . ?
C1 H1A 0.95 . ?
C2 N2 1.39 . ?
C2 H2A 0.95 . ?
N2 C3 1.39 . ?
C3 C4 1.39 . ?
C3 H3A 0.95 . ?
C4 H4A 0.95 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
N3 C6 1.39 . ?
N3 C9 1.39 . ?
N3 C10 1.44(2) . ?
C6 C7 1.39 . ?
C6 H6A 0.95 . ?
C7 N4 1.39 . ?
C7 H7A 0.95 . ?
N4 C8 1.39 . ?
C8 C9 1.39 . ?
C8 H8A 0.95 . ?
C9 H9A 0.95 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
N5 C11 1.39 . ?
N5 C14 1.39 . ?
N5 C15 1.470(18) . ?
C11 C12 1.39 . ?
C11 H11A 0.95 . ?
C12 N6 1.39 . ?
C12 H12A 0.95 . ?
N6 C13 1.39 . ?
C13 C14 1.39 . ?
C13 H13A 0.95 . ?
C14 H14A 0.95 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 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
Br4 Bi1 I4 0.4(3) . . ?
Br4 Bi1 I2 90.5(3) . . ?
I4 Bi1 I2 90.39(17) . . ?
Br4 Bi1 Br3 103.5(4) . . ?
I4 Bi1 Br3 103.9(3) . . ?
I2 Bi1 Br3 96.8(5) . . ?
Br4 Bi1 Br2 91.2(3) . . ?
I4 Bi1 Br2 91.02(19) . . ?
I2 Bi1 Br2 0.6(3) . . ?
Br3 Bi1 Br2 96.7(5) . . ?
Br4 Bi1 I3 97.0(2) . . ?
I4 Bi1 I3 97.40(15) . . ?
I2 Bi1 I3 94.5(2) . . ?
Br3 Bi1 I3 7.0(3) . . ?
Br2 Bi1 I3 94.5(2) . . ?
Br4 Bi1 Br1 170.2(2) . . ?
I4 Bi1 Br1 169.76(12) . . ?
I2 Bi1 Br1 87.90(16) . . ?
Br3 Bi1 Br1 86.3(3) . . ?
Br2 Bi1 Br1 87.27(18) . . ?
I3 Bi1 Br1 92.80(14) . . ?
Br4 Bi1 I1 170.9(6) . . ?
I4 Bi1 I1 170.5(5) . . ?
I2 Bi1 I1 87.4(5) . . ?
Br3 Bi1 I1 85.5(6) . . ?
Br2 Bi1 I1 86.8(5) . . ?
I3 Bi1 I1 91.9(5) . . ?
Br1 Bi1 I1 1.0(6) . . ?
Br4 Bi1 Br5 96.4(5) . . ?
I4 Bi1 Br5 96.5(4) . . ?
I2 Bi1 Br5 171.8(4) . . ?
Br3 Bi1 Br5 85.9(6) . . ?
Br2 Bi1 Br5 171.2(5) . . ?
I3 Bi1 Br5 89.1(5) . . ?
Br1 Bi1 Br5 84.5(4) . . ?
I1 Bi1 Br5 85.1(6) . . ?
Br4 Bi1 I5 95.7(2) . . ?
I4 Bi1 I5 95.83(9) . . ?
I2 Bi1 I5 172.94(15) . . ?
Br3 Bi1 I5 85.0(5) . . ?
Br2 Bi1 I5 172.34(17) . . ?
I3 Bi1 I5 88.06(17) . . ?
Br1 Bi1 I5 85.39(7) . . ?
I1 Bi1 I5 85.9(5) . . ?
Br5 Bi1 I5 1.3(5) . . ?
Br4 Bi1 I6 90.00(18) . . ?
I4 Bi1 I6 89.65(10) . . ?
I2 Bi1 I6 97.81(13) . . ?
Br3 Bi1 I6 160.0(3) . . ?
Br2 Bi1 I6 97.72(14) . . ?
I3 Bi1 I6 165.80(13) . . ?
Br1 Bi1 I6 80.59(8) . . ?
I1 Bi1 I6 81.6(5) . . ?
Br5 Bi1 I6 77.9(4) . . ?
I5 Bi1 I6 78.94(5) . . ?
Br7 Bi2 I8 83.2(3) . . ?
Br7 Bi2 Br8 93.73(18) . . ?
I8 Bi2 Br8 12.8(2) . . ?
Br7 Bi2 Br9 95.3(4) . . ?
I8 Bi2 Br9 84.9(4) . . ?
Br8 Bi2 Br9 91.0(3) . . ?
Br7 Bi2 I7 9.0(4) . . ?
I8 Bi2 I7 90.1(5) . . ?
Br8 Bi2 I7 101.2(4) . . ?
Br9 Bi2 I7 90.3(6) . . ?
Br7 Bi2 I9 94.0(8) . . ?
I8 Bi2 I9 89.5(8) . . ?
Br8 Bi2 I9 95.9(7) . . ?
Br9 Bi2 I9 5.0(9) . . ?
I7 Bi2 I9 88.4(9) . . ?
Br7 Bi2 Br1 85.45(16) . . ?
I8 Bi2 Br1 91.7(3) . . ?
Br8 Bi2 Br1 85.45(13) . . ?
Br9 Bi2 Br1 176.4(3) . . ?
I7 Bi2 Br1 90.9(5) . . ?
I9 Bi2 Br1 178.6(7) . . ?
Br7 Bi2 I1 85.7(5) . . ?
I8 Bi2 I1 91.4(6) . . ?
Br8 Bi2 I1 85.1(5) . . ?
Br9 Bi2 I1 176.0(5) . . ?
I7 Bi2 I1 91.2(7) . . ?
I9 Bi2 I1 178.9(8) . . ?
Br1 Bi2 I1 0.4(5) . . ?
Br7 Bi2 Br5 169.7(4) . . ?
I8 Bi2 Br5 104.2(5) . . ?
Br8 Bi2 Br5 92.7(4) . . ?
Br9 Bi2 Br5 92.6(5) . . ?
I7 Bi2 Br5 165.7(6) . . ?
I9 Bi2 Br5 93.3(9) . . ?
Br1 Bi2 Br5 87.0(4) . . ?
I1 Bi2 Br5 86.8(7) . . ?
Br7 Bi2 I5 169.59(18) . . ?
I8 Bi2 I5 104.0(2) . . ?
Br8 Bi2 I5 92.54(10) . . ?
Br9 Bi2 I5 92.9(3) . . ?
I7 Bi2 I5 165.8(5) . . ?
I9 Bi2 I5 93.6(8) . . ?
Br1 Bi2 I5 86.77(8) . . ?
I1 Bi2 I5 86.6(5) . . ?
Br5 Bi2 I5 0.3(5) . . ?
Br7 Bi2 I6 92.02(16) . . ?
I8 Bi2 I6 173.0(3) . . ?
Br8 Bi2 I6 166.51(11) . . ?
Br9 Bi2 I6 100.7(3) . . ?
I7 Bi2 I6 85.7(5) . . ?
I9 Bi2 I6 95.8(7) . . ?
Br1 Bi2 I6 82.86(7) . . ?
I1 Bi2 I6 83.2(4) . . ?
Br5 Bi2 I6 80.0(4) . . ?
I5 Bi2 I6 80.14(4) . . ?
Bi2 Br1 Bi1 84.27(7) . . ?
Bi2 Br5 Bi1 80.6(5) . . ?
I8 Br8 Bi2 80.3(18) . . ?
Bi2 I1 Bi1 83.3(6) . . ?
Bi2 I5 Bi1 79.50(4) . . ?
Bi2 I6 Bi1 78.14(3) . . ?
Br8 I8 Bi2 86.9(18) . . ?
C1 N1 C4 120 . . ?
C1 N1 C5 119.4(11) . . ?
C4 N1 C5 120.6(11) . . ?
N1 C1 C2 120 . . ?
N1 C1 H1A 120 . . ?
C2 C1 H1A 120 . . ?
C1 C2 N2 120 . . ?
C1 C2 H2A 120 . . ?
N2 C2 H2A 120 . . ?
C3 N2 C2 120 . . ?
N2 C3 C4 120 . . ?
N2 C3 H3A 120 . . ?
C4 C3 H3A 120 . . ?
C3 C4 N1 120 . . ?
C3 C4 H4A 120 . . ?
N1 C4 H4A 120 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 N3 C9 120 . . ?
C6 N3 C10 120.6(13) . . ?
C9 N3 C10 119.3(13) . . ?
N3 C6 C7 120 . . ?
N3 C6 H6A 120 . . ?
C7 C6 H6A 120 . . ?
N4 C7 C6 120 . . ?
N4 C7 H7A 120 . . ?
C6 C7 H7A 120 . . ?
C7 N4 C8 120 . . ?
N4 C8 C9 120 . . ?
N4 C8 H8A 120 . . ?
C9 C8 H8A 120 . . ?
C8 C9 N3 120 . . ?
C8 C9 H9A 120 . . ?
N3 C9 H9A 120 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 N5 C14 120 . . ?
C11 N5 C15 119.0(10) . . ?
C14 N5 C15 121.0(10) . . ?
N5 C11 C12 120 . . ?
N5 C11 H11A 120 . . ?
C12 C11 H11A 120 . . ?
N6 C12 C11 120 . . ?
N6 C12 H12A 120 . . ?
C11 C12 H12A 120 . . ?
C12 N6 C13 120 . . ?
C14 C13 N6 120 . . ?
C14 C13 H13A 120 . . ?
N6 C13 H13A 120 . . ?
C13 C14 N5 120 . . ?
C13 C14 H14A 120 . . ?
N5 C14 H14A 120 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

