# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_compound6
_database_code_depnum_ccdc_archive 'CCDC 2025569'
loop_
_audit_author_name
_audit_author_address
'Jakob Moebs'
;Philipps University Marburg
Germany
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, I5, 4(C5 H6 N)'
_chemical_formula_sum            'C20 H24 Bi2 I14 N4'
_chemical_formula_weight         2514.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   18.3316(10)
_cell_length_b                   32.7986(14)
_cell_length_c                   8.1963(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4928.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    29177
_cell_measurement_temperature    100
_cell_measurement_theta_max      54.22
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    15.921
_exptl_absorpt_correction_T_max  0.2186
_exptl_absorpt_correction_T_min  0.0004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4320
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            83000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.937
_diffrn_reflns_theta_min         1.242
_diffrn_ambient_temperature      100
_diffrn_detector                 'imaging plate area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'area detetor, ω scans'
_diffrn_radiation_collimation    '0.5 mm diameter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'STOE C-Tech Mo tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3336
_reflns_number_total             5406
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         5.265
_refine_diff_density_min         -2.045
_refine_diff_density_rms         0.331
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         5406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0714
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1344P)²+50.6986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2374
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Shared sites
{N1, C1}
{C4, N3}
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C1)
Uanis(C4) = Uanis(N3)
Uanis(N3) = Uanis(C4)
4. Others
 Fixed Sof: I8(0.5) C4(0.5) H5A(0.5) H5B(0.5) N1(0.5) H1(0.5) H2A(0.5)
 H2B(0.5) H3A(0.5) H3B(0.5) C1(0.5) H1A(0.5) N3(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5A), C5(H5B), N1(H1), C2(H2A), C2(H2B), C3(H3A), C3(H3B),
 C8(H8), N2(H2), C11(H11), C7(H7), C10(H10), C9(H9), C1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.46850(4) 0.18529(2) 0.96966(10) 0.0520(3) Uani 1 1 d . . . . .
I1 I 0.53848(9) 0.250000 1.2270(2) 0.0543(4) Uani 1 2 d S T P . .
I2 I 0.33159(10) 0.250000 0.9726(2) 0.0563(5) Uani 1 2 d S T P . .
I3 I 0.53906(10) 0.250000 0.7140(2) 0.0554(5) Uani 1 2 d S T P . .
I4 I 0.60671(7) 0.13864(4) 0.97088(19) 0.0625(4) Uani 1 1 d . . . . .
I5 I 0.40709(7) 0.13366(4) 1.22761(17) 0.0582(4) Uani 1 1 d . . . . .
I6 I 0.40350(7) 0.13157(4) 0.72263(17) 0.0576(4) Uani 1 1 d . . . . .
I7 I 0.76480(9) 0.05875(5) 1.0521(3) 0.0989(7) Uani 1 1 d . . . . .
I9 I 0.43550(15) 0.01993(5) 1.4735(3) 0.1106(8) Uani 1 1 d . . . . .
I8 I 0.74633(15) 0.00172(8) 0.7983(5) 0.0788(10) Uani 0.5 1 d . . . . .
C4 C 0.7210(10) 0.2292(5) 0.986(2) 0.061(5) Uani 0.5 1 d . . . A 3
H4 H 0.676743 0.214698 0.970004 0.073 Uiso 1 1 calc R . . . .
C6 C 0.8475(11) 0.2287(6) 1.030(2) 0.061(5) Uani 1 1 d . . . . .
H6 H 0.891292 0.213687 1.045265 0.073 Uiso 1 1 calc R . . . .
C5 C 0.7822(11) 0.2094(6) 1.007(2) 0.056(5) Uani 1 1 d . . . . .
H5A H 0.781254 0.180413 1.006791 0.067 Uiso 0.5 1 calc R . . A 3
H5B H 0.781254 0.180413 1.006791 0.067 Uiso 0.5 1 calc R . . A 4
N1 N 0.4952(11) 0.0412(6) 0.977(3) 0.071(6) Uani 0.5 1 d . . . B 1
H1 H 0.492895 0.067494 0.956739 0.085 Uiso 0.5 1 calc R . . B 1
C2 C 0.5568(14) 0.0256(7) 1.042(4) 0.100(10) Uani 1 1 d . . . . .
H2A H 0.594713 0.043312 1.076622 0.120 Uiso 0.5 1 calc R . . B 1
H2B H 0.594713 0.043312 1.076622 0.120 Uiso 0.5 1 calc R . . B 2
C3 C 0.4350(14) 0.0168(6) 0.942(4) 0.103(10) Uani 1 1 d . . . . .
H3A H 0.389973 0.028359 0.908453 0.123 Uiso 0.5 1 calc R . . B 1
H3B H 0.389973 0.028359 0.908453 0.123 Uiso 0.5 1 calc R . . B 2
C8 C 0.3486(17) -0.0882(7) 1.491(3) 0.087(8) Uani 1 1 d . . . . .
H8 H 0.350460 -0.059349 1.479367 0.104 Uiso 1 1 calc R . . . .
N2 N 0.4078(12) -0.1517(6) 1.531(3) 0.095(7) Uani 1 1 d . . . . .
H2 H 0.447715 -0.166002 1.548250 0.114 Uiso 1 1 calc R . . . .
C11 C 0.3415(13) -0.1717(8) 1.524(3) 0.074(6) Uani 1 1 d . . . . .
H11 H 0.338489 -0.200243 1.541134 0.089 Uiso 1 1 calc R . . . .
C7 C 0.4129(16) -0.1127(9) 1.514(3) 0.084(7) Uani 1 1 d . . . . .
H7 H 0.459461 -0.100022 1.516174 0.101 Uiso 1 1 calc R . . . .
C10 C 0.2816(13) -0.1497(8) 1.492(3) 0.086(8) Uani 1 1 d . . . . .
H10 H 0.236053 -0.162756 1.473468 0.103 Uiso 1 1 calc R . . . .
C9 C 0.2871(16) -0.1087(7) 1.486(3) 0.089(8) Uani 1 1 d . . . . .
H9 H 0.243078 -0.093528 1.478412 0.107 Uiso 1 1 calc R . . . .
C1 C 0.4952(11) 0.0412(6) 0.977(3) 0.071(6) Uani 0.5 1 d . . . B 2
H1A H 0.492714 0.069587 0.955107 0.085 Uiso 0.5 1 calc R . . B 2
N3 N 0.7210(10) 0.2292(5) 0.986(2) 0.061(5) Uani 0.5 1 d . . . A 4


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I1 3.2555(16) . ?
Bi1 I2 3.2869(16) . ?
Bi1 I3 3.2506(16) . ?
Bi1 I4 2.9598(14) . ?
Bi1 I5 2.9335(15) . ?
Bi1 I6 2.9367(14) . ?
I7 I8 2.836(4) 2_655 ?
I7 I8 2.818(4) . ?
I9 I9 2.737(5) 5_658 ?
C4 C4 1.36(3) 8_565 ?
C4 C5 1.31(3) . ?
C6 C6 1.40(4) 8_565 ?
C6 C5 1.37(3) . ?
C5 N3 1.31(3) . ?
N1 C2 1.35(3) . ?
N1 C3 1.39(3) . ?
C2 C3 1.40(3) 5_657 ?
C2 C1 1.35(3) . ?
C3 C1 1.39(3) . ?
C8 C7 1.44(4) . ?
C8 C9 1.31(4) . ?
N2 C11 1.38(3) . ?
N2 C7 1.29(3) . ?
C11 C10 1.34(3) . ?
C10 C9 1.35(3) . ?

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
I1 Bi1 I2 82.83(4) . . ?
I3 Bi1 I1 80.51(4) . . ?
I3 Bi1 I2 83.52(4) . . ?
I4 Bi1 I1 89.86(4) . . ?
I4 Bi1 I2 170.89(4) . . ?
I4 Bi1 I3 89.95(4) . . ?
I5 Bi1 I1 93.47(4) . . ?
I5 Bi1 I2 94.26(4) . . ?
I5 Bi1 I3 173.79(4) . . ?
I5 Bi1 I4 91.59(4) . . ?
I5 Bi1 I6 89.70(4) . . ?
I6 Bi1 I1 176.13(4) . . ?
I6 Bi1 I2 94.74(4) . . ?
I6 Bi1 I3 96.25(4) . . ?
I6 Bi1 I4 92.26(4) . . ?
Bi1 I1 Bi1 81.37(5) . 8_565 ?
Bi1 I2 Bi1 80.43(5) . 8_565 ?
Bi1 I3 Bi1 81.52(5) . 8_565 ?
I8 I7 I8 93.01(5) . 2_655 ?
I7 I8 I7 176.24(12) . 2_654 ?
C5 C4 C4 119.8(11) . 8_565 ?
C5 C6 C6 117.6(11) . 8_565 ?
C4 C5 C6 122.6(18) . . ?
N3 C5 C6 122.6(18) . . ?
C2 N1 C3 122(2) . . ?
N1 C2 C3 120(2) . 5_657 ?
C1 C2 C3 120(2) . 5_657 ?
N1 C3 C2 118(2) . 5_657 ?
C9 C8 C7 115(2) . . ?
C7 N2 C11 122(2) . . ?
C10 C11 N2 118(2) . . ?
N2 C7 C8 121(3) . . ?
C11 C10 C9 119(2) . . ?
C8 C9 C10 125(3) . . ?
C2 C1 C3 122(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound3-Bi
_database_code_depnum_ccdc_archive 'CCDC 2025573'
loop_
_audit_author_name
_audit_author_address
'Jakob Moebs'
;Philipps University Marburg
Germany
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, 2(C4 H10 O2), 3(C5 H6 N)'
_chemical_formula_sum            'C23 H38 Bi2 I9 N3 O4'
_chemical_formula_weight         1980.62
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5623(6)
_cell_length_b                   18.8440(10)
_cell_length_c                   28.796(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4646.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12754
_cell_measurement_temperature    100
_cell_measurement_theta_max      53.7
_cell_measurement_theta_min      2.8
_shelx_estimated_absorpt_T_max   0.410
_shelx_estimated_absorpt_T_min   0.182
_exptl_absorpt_coefficient_mu    13.572
_exptl_absorpt_correction_T_max  0.4012
_exptl_absorpt_correction_T_min  0.2975
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-Red32 1.63.4'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.831
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3488
_exptl_crystal_size_max          0.1905
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.829
_diffrn_reflns_theta_min         1.414
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'imaging plate area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'area detetor, ω scans'
_diffrn_radiation_collimation    '0.5 mm diameter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'STOE C-Tech Mo tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3906
_reflns_number_total             4939
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         2.111
_refine_diff_density_min         -1.928
_refine_diff_density_rms         0.274
_refine_ls_abs_structure_details 
;
 Flack x determined using 1470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4939
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C10 \\sim N2-C14
 with sigma of 0.02
 C10-C11 \\sim C11-C12 \\sim C12-C13 \\sim C13-C14
 with sigma of 0.02
 N2-C13 \\sim N2-C11
 with sigma of 0.04
 C12-C14 \\sim C12-C10 \\sim C13-C11 \\sim C14-C10
 with sigma of 0.04
3. Restrained planarity
 N2, C10, C11, C12, C13, C14
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N2 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 N2, C10, C11, C12, C13, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: N2(0.5) H2(0.5) C10(0.5) H10(0.5) C11(0.5) H11(0.5) C12(0.5)
 H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C5(H5), C8(H8), C9(H9), N2(H2), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14)
7.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.47187(7) 0.18283(3) 0.32328(2) 0.02068(14) Uani 1 1 d . . . . .
I1 I 0.19811(12) 0.24453(6) 0.37116(3) 0.0285(3) Uani 1 1 d . . . . .
I2 I 0.500000 0.31287(8) 0.250000 0.0276(4) Uani 1 2 d S T P . .
I3 I 0.25344(13) 0.11947(6) 0.24223(3) 0.0275(3) Uani 1 1 d . . . . .
I4 I 0.45992(14) 0.05497(6) 0.38209(4) 0.0320(3) Uani 1 1 d . . . . .
I5 I 0.70263(13) 0.25717(6) 0.38287(3) 0.0301(3) Uani 1 1 d . . . . .
O1 O 0.1707(13) 0.3803(6) 0.4634(4) 0.030(3) Uani 1 1 d . . . . .
O2 O 0.4681(13) 0.3955(6) 0.4999(4) 0.032(3) Uani 1 1 d . . . . .
N1 N -0.1445(16) -0.0549(7) 0.3978(5) 0.028(3) Uani 1 1 d . . . . .
H1 H -0.193852 -0.087899 0.413655 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2233(18) 0.3351(8) 0.4991(5) 0.028(4) Uani 1 1 d . . . . .
H2A H 0.171571 0.288301 0.496197 0.034 Uiso 1 1 calc R . . . .
H2B H 0.194712 0.355477 0.529626 0.034 Uiso 1 1 calc R . . . .
C1 C 0.0052(18) 0.3864(10) 0.4616(6) 0.037(4) Uani 1 1 d . . . . .
H1A H -0.023539 0.426792 0.441938 0.055 Uiso 1 1 calc GR . . . .
H1B H -0.035713 0.393676 0.492984 0.055 Uiso 1 1 calc GR . . . .
H1C H -0.039173 0.342764 0.448516 0.055 Uiso 1 1 calc GR . . . .
C6 C -0.041(2) 0.0595(9) 0.3929(5) 0.031(4) Uani 1 1 d . . . . .
H6 H -0.020309 0.104568 0.406372 0.037 Uiso 1 1 calc R . . . .
C4 C 0.6328(18) 0.3928(11) 0.4969(7) 0.044(5) Uani 1 1 d . . . . .
H4A H 0.663186 0.369244 0.467919 0.066 Uiso 1 1 calc GR . . . .
H4B H 0.674437 0.366158 0.523355 0.066 Uiso 1 1 calc GR . . . .
H4C H 0.674998 0.441152 0.497277 0.066 Uiso 1 1 calc GR . . . .
C7 C 0.0087(18) 0.0455(9) 0.3497(6) 0.030(4) Uani 1 1 d . . . . .
H7 H 0.062663 0.081176 0.332786 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3963(19) 0.3257(9) 0.4966(6) 0.033(4) Uani 1 1 d . . . . .
H3A H 0.432545 0.295153 0.522461 0.040 Uiso 1 1 calc R . . . .
H3B H 0.425533 0.302721 0.466940 0.040 Uiso 1 1 calc R . . . .
C5 C -0.1223(19) 0.0092(9) 0.4181(5) 0.027(4) Uani 1 1 d . . . . .
H5 H -0.160898 0.019025 0.448323 0.032 Uiso 1 1 calc R . . . .
C8 C -0.017(2) -0.0195(9) 0.3293(6) 0.042(4) Uani 1 1 d . . . . .
H8 H 0.017923 -0.029519 0.298709 0.050 Uiso 1 1 calc R . . . .
C9 C -0.097(2) -0.0704(9) 0.3561(6) 0.033(4) Uani 1 1 d . . . . .
H9 H -0.116166 -0.116229 0.343588 0.040 Uiso 1 1 calc R . . . .
N2 N -0.008(4) 0.3000(15) 0.2620(9) 0.042(9) Uani 0.5 1 d D U . A -1
H2 H -0.012693 0.256027 0.272169 0.050 Uiso 0.5 1 calc R . . A -1
C10 C -0.071(4) 0.3530(19) 0.2883(11) 0.043(10) Uani 0.5 1 d D U . A -1
H10 H -0.121895 0.342779 0.316940 0.051 Uiso 0.5 1 calc R . . A -1
C11 C -0.060(6) 0.4223(16) 0.2722(17) 0.054(12) Uani 0.5 1 d D U . A -1
H11 H -0.104719 0.459940 0.289655 0.065 Uiso 0.5 1 calc R . . A -1
C12 C 0.016(7) 0.4368(15) 0.2309(17) 0.049(11) Uani 0.5 1 d D U . A -1
H12 H 0.027277 0.484595 0.220905 0.059 Uiso 0.5 1 calc R . . A -1
C13 C 0.075(5) 0.3824(16) 0.2040(14) 0.048(10) Uani 0.5 1 d D U . A -1
H13 H 0.123721 0.392316 0.175072 0.058 Uiso 0.5 1 calc R . . A -1
C14 C 0.063(4) 0.3135(19) 0.2198(10) 0.034(9) Uani 0.5 1 d D U . A -1
H14 H 0.103489 0.275513 0.201815 0.041 Uiso 0.5 1 calc R . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I1 2.9576(12) . ?
Bi1 I2 3.2429(13) . ?
Bi1 I3 3.2204(12) . ?
Bi1 I3 3.2429(12) 3_655 ?
Bi1 I4 2.9468(12) . ?
Bi1 I5 2.9682(12) . ?
O1 C2 1.410(18) . ?
O1 C1 1.423(19) . ?
O2 C4 1.414(19) . ?
O2 C3 1.456(19) . ?
N1 C5 1.36(2) . ?
N1 C9 1.30(2) . ?
C2 C3 1.49(2) . ?
C6 C7 1.34(2) . ?
C6 C5 1.38(2) . ?
C7 C8 1.37(2) . ?
C8 C9 1.41(2) . ?
N2 C10 1.37(3) . ?
N2 C14 1.38(3) . ?
C10 C11 1.39(2) . ?
C11 C12 1.38(2) . ?
C12 C13 1.38(2) . ?
C13 C14 1.38(2) . ?

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
I1 Bi1 I2 93.74(3) . . ?
I1 Bi1 I3 172.20(3) . 3_655 ?
I1 Bi1 I3 91.34(3) . . ?
I1 Bi1 I5 94.16(4) . . ?
I2 Bi1 I3 81.13(3) . 3_655 ?
I3 Bi1 I2 81.47(3) . . ?
I3 Bi1 I3 82.13(4) . 3_655 ?
I4 Bi1 I1 91.49(3) . . ?
I4 Bi1 I2 173.94(4) . . ?
I4 Bi1 I3 93.35(3) . 3_655 ?
I4 Bi1 I3 95.35(3) . . ?
I4 Bi1 I5 94.40(3) . . ?
I5 Bi1 I2 88.29(3) . . ?
I5 Bi1 I3 168.67(3) . . ?
I5 Bi1 I3 91.56(3) . 3_655 ?
Bi1 I2 Bi1 81.83(4) 3_655 . ?
Bi1 I3 Bi1 82.18(3) . 3_655 ?
C2 O1 C1 113.1(12) . . ?
C4 O2 C3 112.6(14) . . ?
C9 N1 C5 123.6(14) . . ?
O1 C2 C3 110.7(14) . . ?
C7 C6 C5 120.7(16) . . ?
C6 C7 C8 121.3(16) . . ?
O2 C3 C2 108.0(14) . . ?
N1 C5 C6 117.2(15) . . ?
C7 C8 C9 116.8(16) . . ?
N1 C9 C8 120.3(16) . . ?
C10 N2 C14 122(4) . . ?
N2 C10 C11 118(2) . . ?
C12 C11 C10 120(2) . . ?
C13 C12 C11 121(2) . . ?
C14 C13 C12 119(2) . . ?
C13 C14 N2 120(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound3-Sb
_database_code_depnum_ccdc_archive 'CCDC 2025574'
loop_
_audit_author_name
_audit_author_address
'Jakob Moebs'
;Philipps University Marburg
Germany
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I9 Sb2, 2(C4 H10 O2), 3(C5 H6 N)'
_chemical_formula_sum            'C23 H38 I9 N3 O4 Sb2'
_chemical_formula_weight         1806.16
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5313(5)
_cell_length_b                   18.8548(10)
_cell_length_c                   28.583(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4597.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14013
_cell_measurement_temperature    100
_cell_measurement_theta_max      54.0
_cell_measurement_theta_min      2.8
_shelx_estimated_absorpt_T_max   0.386
_shelx_estimated_absorpt_T_min   0.222
_exptl_absorpt_coefficient_mu    7.246
_exptl_absorpt_correction_T_max  0.3653
_exptl_absorpt_correction_T_min  0.1840
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-Red32 1.65'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.29738
_exptl_crystal_size_mid          0.24907
_exptl_crystal_size_min          0.16201
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            13992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.977
_diffrn_reflns_theta_min         1.425
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3281
_reflns_number_total             4906
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         2.545
_refine_diff_density_min         -1.465
_refine_diff_density_rms         0.285
_refine_ls_abs_structure_details 
;
 Flack x determined using 1140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4906
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0933P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1647
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C10 \\sim N2-C14
 with sigma of 0.02
 C10-C11 \\sim C11-C12 \\sim C12-C13 \\sim C13-C14
 with sigma of 0.02
 N2-C13 \\sim N2-C11
 with sigma of 0.04
 C12-C14 \\sim C12-C10 \\sim C13-C11 \\sim C14-C10
 with sigma of 0.04
3. Restrained planarity
 N2, C10, C11, C12, C13, C14
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N2 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 N2, C10, C11, C12, C13, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: N2(0.5) H2(0.5) C10(0.5) H10(0.5) C11(0.5) H11(0.5) C12(0.5)
 H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), N2(H2), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14)
7.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Sb1 Sb -0.52981(19) -0.81772(9) -0.67760(5) 0.0427(4) Uani 1 1 d . . . . .
I1 I -0.79786(18) -0.75700(10) -0.63059(6) 0.0518(4) Uani 1 1 d . . . . .
I2 I -0.500000 -0.68856(13) -0.750000 0.0506(6) Uani 1 2 d S T P . .
I3 I -0.7454(2) -0.88064(10) -0.75827(6) 0.0504(4) Uani 1 1 d . . . . .
I4 I -0.30534(19) -0.74632(10) -0.61775(5) 0.0533(4) Uani 1 1 d . . . . .
I5 I -0.5431(2) -0.94172(9) -0.61926(6) 0.0536(4) Uani 1 1 d . . . . .
O1 O -0.8369(18) -0.6196(10) -0.5387(6) 0.056(4) Uani 1 1 d . . . . .
O2 O -0.544(2) -0.6058(9) -0.5013(6) 0.055(4) Uani 1 1 d . . . . .
C2 C -0.617(3) -0.6705(12) -0.5054(9) 0.052(6) Uani 1 1 d . . . . .
H2A H -0.576957 -0.702917 -0.480883 0.062 Uiso 1 1 calc R . . . .
H2B H -0.591301 -0.691498 -0.536278 0.062 Uiso 1 1 calc R . . . .
C3 C -0.785(3) -0.6633(15) -0.5009(9) 0.056(6) Uani 1 1 d . . . . .
H3A H -0.835863 -0.710434 -0.502475 0.067 Uiso 1 1 calc R . . . .
H3B H -0.811687 -0.641103 -0.470558 0.067 Uiso 1 1 calc R . . . .
C1 C -0.375(3) -0.6089(14) -0.5010(11) 0.057(6) Uani 1 1 d . . . . .
H1A H -0.337244 -0.620284 -0.532469 0.086 Uiso 1 1 calc GR . . . .
H1B H -0.340545 -0.645571 -0.479032 0.086 Uiso 1 1 calc GR . . . .
H1C H -0.332972 -0.562822 -0.491282 0.086 Uiso 1 1 calc GR . . . .
C4 C -1.005(2) -0.6149(14) -0.5417(10) 0.053(6) Uani 1 1 d . . . . .
H4A H -1.034756 -0.589765 -0.570375 0.079 Uiso 1 1 calc GR . . . .
H4B H -1.045725 -0.588917 -0.514485 0.079 Uiso 1 1 calc GR . . . .
H4C H -1.050443 -0.662700 -0.542124 0.079 Uiso 1 1 calc GR . . . .
N1 N -0.645(2) -0.5516(10) -0.6020(7) 0.048(5) Uani 1 1 d . . . . .
H1 H -0.694677 -0.583318 -0.584955 0.057 Uiso 1 1 calc R . . . .
C5 C -0.600(4) -0.5704(16) -0.6455(11) 0.070(8) Uani 1 1 d . . . . .
H5 H -0.625357 -0.615631 -0.658190 0.084 Uiso 1 1 calc R . . . .
C6 C -0.516(4) -0.5206(14) -0.6709(10) 0.069(9) Uani 1 1 d . . . . .
H6 H -0.478055 -0.531410 -0.701307 0.083 Uiso 1 1 calc R . . . .
C7 C -0.488(3) -0.4552(14) -0.6511(10) 0.056(7) Uani 1 1 d . . . . .
H7 H -0.428388 -0.421050 -0.667824 0.067 Uiso 1 1 calc R . . . .
C8 C -0.545(3) -0.4387(16) -0.6080(10) 0.061(7) Uani 1 1 d . . . . .
H8 H -0.532531 -0.392467 -0.595299 0.073 Uiso 1 1 calc R . . . .
C9 C -0.620(3) -0.4902(15) -0.5837(10) 0.055(7) Uani 1 1 d . . . . .
H9 H -0.654710 -0.480951 -0.552710 0.066 Uiso 1 1 calc R . . . .
N2 N -0.992(5) -0.6986(18) -0.7616(12) 0.048(10) Uani 0.5 1 d D U . A -1
H2 H -0.984986 -0.742444 -0.771922 0.058 Uiso 0.5 1 calc R . . A -1
C10 C -1.072(5) -0.687(2) -0.7218(12) 0.044(10) Uani 0.5 1 d D U . A -1
H10 H -1.118551 -0.725097 -0.704838 0.053 Uiso 0.5 1 calc R . . A -1
C11 C -1.086(5) -0.6186(19) -0.7067(15) 0.046(10) Uani 0.5 1 d D U . A -1
H11 H -1.141212 -0.608353 -0.678733 0.055 Uiso 0.5 1 calc R . . A -1
C12 C -1.019(8) -0.5648(18) -0.732(2) 0.058(13) Uani 0.5 1 d D U . A -1
H12 H -1.027826 -0.517309 -0.720895 0.070 Uiso 0.5 1 calc R . . A -1
C13 C -0.940(7) -0.579(2) -0.772(2) 0.050(11) Uani 0.5 1 d D U . A -1
H13 H -0.899700 -0.541160 -0.790555 0.060 Uiso 0.5 1 calc R . . A -1
C14 C -0.920(6) -0.647(3) -0.7866(15) 0.050(11) Uani 0.5 1 d D U . A -1
H14 H -0.857928 -0.658474 -0.813200 0.060 Uiso 0.5 1 calc R . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 I1 2.889(2) . ?
Sb1 I2 3.206(2) . ?
Sb1 I3 3.179(2) . ?
Sb1 I3 3.206(2) 3_453 ?
Sb1 I4 2.899(2) . ?
Sb1 I5 2.874(2) . ?
O1 C3 1.43(3) . ?
O1 C4 1.44(3) . ?
O2 C2 1.37(3) . ?
O2 C1 1.45(3) . ?
C2 C3 1.45(3) . ?
N1 C5 1.35(4) . ?
N1 C9 1.29(3) . ?
C5 C6 1.39(4) . ?
C6 C7 1.38(4) . ?
C7 C8 1.36(4) . ?
C8 C9 1.36(4) . ?
N2 C10 1.35(3) . ?
N2 C14 1.35(3) . ?
C10 C11 1.37(3) . ?
C11 C12 1.36(3) . ?
C12 C13 1.37(3) . ?
C13 C14 1.36(3) . ?

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
I1 Sb1 I2 93.55(6) . . ?
I1 Sb1 I3 172.85(7) . 3_453 ?
I1 Sb1 I3 91.56(6) . . ?
I1 Sb1 I4 93.69(7) . . ?
I2 Sb1 I3 81.60(5) . 3_453 ?
I3 Sb1 I2 82.02(5) . . ?
I3 Sb1 I3 82.59(6) . 3_453 ?
I4 Sb1 I2 88.61(6) . . ?
I4 Sb1 I3 91.46(6) . 3_453 ?
I4 Sb1 I3 169.53(7) . . ?
I5 Sb1 I1 91.21(7) . . ?
I5 Sb1 I2 174.65(7) . . ?
I5 Sb1 I3 95.42(7) . . ?
I5 Sb1 I3 93.42(6) . 3_453 ?
I5 Sb1 I4 93.52(7) . . ?
Sb1 I2 Sb1 81.13(8) . 3_453 ?
Sb1 I3 Sb1 81.54(6) . 3_453 ?
C3 O1 C4 113.0(19) . . ?
C2 O2 C1 114(2) . . ?
O2 C2 C3 111(2) . . ?
O1 C3 C2 107(2) . . ?
C9 N1 C5 124(2) . . ?
N1 C5 C6 117(3) . . ?
C7 C6 C5 119(3) . . ?
C8 C7 C6 121(3) . . ?
C9 C8 C7 118(3) . . ?
N1 C9 C8 121(3) . . ?
C14 N2 C10 124(5) . . ?
N2 C10 C11 117(3) . . ?
C12 C11 C10 120(2) . . ?
C11 C12 C13 120(2) . . ?
C14 C13 C12 120(2) . . ?
N2 C14 C13 117(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 2025572'
loop_
_audit_author_name
_audit_author_address
'Jakob Moebs'
;Philipps University Marburg
Germany
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, 3(C5 H6 N)'
_chemical_formula_sum            'C15 H18 Bi2 I9 N3'
_chemical_formula_weight         1800.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   14.6088(6)
_cell_length_b                   23.6348(9)
_cell_length_c                   9.9053(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3420.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.410
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0699 after correction.
The Ratio of minimum to maximum transmission is 0.7167.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    3.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3088
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1239
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            53756
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.306
_diffrn_reflns_theta_min         2.229
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2514
_reflns_number_total             3188
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.928
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.247
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0120P)²+17.2364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0468
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Shared sites
{N2, C6}
3. Restrained distances
 C6-H2A
 0.95 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C6) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2) = Uanis(C6)
5. Others
 Fixed Sof: N2(0.5) C6(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C7(H7), C8(H8), C4(H4), C3(H3), C1(H1A), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.68099(2) 0.65932(2) 0.50504(3) 0.00959(7) Uani 1 1 d . . . . .
I1 I 0.73444(5) 0.750000 0.27092(7) 0.01085(17) Uani 1 2 d S T P . .
I2 I 0.52030(5) 0.750000 0.55087(8) 0.01384(18) Uani 1 2 d S T P . .
I6 I 0.79214(5) 0.750000 0.68501(7) 0.01216(17) Uani 1 2 d S T P . .
I3 I 0.56216(4) 0.59165(2) 0.32241(5) 0.01324(13) Uani 1 1 d . . . . .
I4 I 0.62555(3) 0.58878(2) 0.74012(5) 0.01473(13) Uani 1 1 d . . . . .
I5 I 0.84026(4) 0.58431(2) 0.45966(5) 0.01486(13) Uani 1 1 d . . . . .
N1 N 0.3373(5) 0.5318(3) 0.5348(6) 0.0176(17) Uani 1 1 d . . . . .
H1 H 0.342166 0.494706 0.540107 0.021 Uiso 1 1 calc R . . . .
N2 N 1.0820(6) 0.7211(3) 0.5706(7) 0.0191(19) Uani 0.5 1 d . U . A 1
C2 C 0.3733(5) 0.6208(3) 0.6199(8) 0.0124(19) Uani 1 1 d . . . . .
H2 H 0.403153 0.643463 0.685671 0.015 Uiso 1 1 calc R . . . .
C7 C 1.0349(5) 0.6920(3) 0.4787(8) 0.0154(19) Uani 1 1 d . . . . .
H7 H 1.035211 0.651777 0.479851 0.018 Uiso 1 1 calc R . . A 1
C8 C 0.9858(5) 0.7207(3) 0.3820(8) 0.016(2) Uani 1 1 d . . . . .
H8 H 0.952108 0.700488 0.315653 0.019 Uiso 1 1 calc R . . . .
C4 C 0.2800(6) 0.6119(4) 0.4229(8) 0.020(2) Uani 1 1 d . . . . .
H4 H 0.245655 0.628457 0.351694 0.024 Uiso 1 1 calc R . . . .
C3 C 0.3239(5) 0.6455(3) 0.5181(8) 0.0150(19) Uani 1 1 d . . . . .
H3 H 0.319631 0.685565 0.512692 0.018 Uiso 1 1 calc R . . . .
C1 C 0.3790(5) 0.5631(4) 0.6255(8) 0.016(2) Uani 1 1 d . . . . .
H1A H 0.413305 0.545586 0.695437 0.019 Uiso 1 1 calc R . . . .
C5 C 0.2873(6) 0.5545(4) 0.4338(9) 0.023(2) Uani 1 1 d . . . . .
H5 H 0.257325 0.530603 0.370598 0.028 Uiso 1 1 calc R . . . .
C6 C 1.0820(6) 0.7211(3) 0.5706(7) 0.0191(19) Uani 0.5 1 d D U . A 2
H2A H 1.118(5) 0.703(3) 0.638(6) 0.03(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I1 3.2529(6) . ?
Bi1 I2 3.2110(6) . ?
Bi1 I6 3.2262(6) . ?
Bi1 I3 2.9738(6) . ?
Bi1 I4 2.9761(6) . ?
Bi1 I5 2.9595(6) . ?
N1 C1 1.314(10) . ?
N1 C5 1.350(10) . ?
N2 N2 1.367(14) 7_575 ?
N2 C7 1.333(11) . ?
C2 C3 1.370(11) . ?
C2 C1 1.367(11) . ?
C7 C8 1.376(11) . ?
C7 C6 1.333(11) . ?
C8 C8 1.385(16) 7_575 ?
C4 C3 1.391(11) . ?
C4 C5 1.365(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 Bi1 I1 80.590(17) . . ?
I2 Bi1 I6 81.165(17) . . ?
I6 Bi1 I1 80.525(17) . . ?
I3 Bi1 I1 93.484(17) . . ?
I3 Bi1 I2 91.042(17) . . ?
I3 Bi1 I6 170.823(17) . . ?
I3 Bi1 I4 90.909(16) . . ?
I4 Bi1 I1 172.839(17) . . ?
I4 Bi1 I2 93.688(18) . . ?
I4 Bi1 I6 94.404(18) . . ?
I5 Bi1 I1 95.604(17) . . ?
I5 Bi1 I2 174.928(18) . . ?
I5 Bi1 I6 94.945(17) . . ?
I5 Bi1 I3 92.543(17) . . ?
I5 Bi1 I4 89.843(17) . . ?
Bi1 I1 Bi1 82.43(2) . 7_575 ?
Bi1 I2 Bi1 83.75(2) . 7_575 ?
Bi1 I6 Bi1 83.26(2) . 7_575 ?
C1 N1 C5 122.2(7) . . ?
C7 N2 N2 121.1(5) . 7_575 ?
C1 C2 C3 119.2(8) . . ?
N2 C7 C8 119.3(8) . . ?
C6 C7 C8 119.3(8) . . ?
C7 C8 C8 119.6(5) . 7_575 ?
C5 C4 C3 118.6(8) . . ?
C2 C3 C4 119.9(7) . . ?
N1 C1 C2 120.4(8) . . ?
N1 C5 C4 119.8(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 2025576'
loop_
_audit_author_name
_audit_author_address
'Jakob Moebs'
;Philipps University Marburg
Germany
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi6 I22, 4(C4 H10 O2), 4(C5 H6 N)'
_chemical_formula_sum            'C36 H64 Bi6 I22 N4 O8'
_chemical_formula_weight         4726.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.4579(8)
_cell_length_b                   19.9643(6)
_cell_length_c                   12.4327(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.255(3)
_cell_angle_gamma                90
_cell_volume                     4612.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    101228
_cell_measurement_temperature    100
_cell_measurement_theta_max      53.7
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   0.143
_shelx_estimated_absorpt_T_min   0.115
_exptl_absorpt_coefficient_mu    18.804
_exptl_absorpt_correction_T_max  0.0012
_exptl_absorpt_correction_T_min  0.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area LANA 1.71.6.0 (STOE, 2017)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4072
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.169
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            94343
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.838
_diffrn_reflns_theta_min         1.497
_diffrn_ambient_temperature      100
_diffrn_detector                 'imaging plate area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'area detetor, ω scans'
_diffrn_radiation_collimation    '0.5 mm diameter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'STOE C-Tech Mo tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7694
_reflns_number_total             9860
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.124
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.236
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         9860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C16(H16A,H16B), C8(H8A,H8B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C1(H1A), C3(H3), C11(H11), C12(H12), C10(H10), C4(H4),
 C13(H13), C2(H2), C14(H14), C5(H5)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Bi3 Bi 0.19574(2) 0.60605(2) 0.29118(3) 0.02497(8) Uani 1 1 d . . . . .
Bi1 Bi 0.69009(2) 0.59597(2) 0.53322(3) 0.02609(8) Uani 1 1 d . . . . .
Bi2 Bi 0.44584(2) 0.60478(2) 0.42694(3) 0.02460(8) Uani 1 1 d . . . . .
I8 I 0.33031(3) 0.67765(3) 0.49368(4) 0.02585(12) Uani 1 1 d . . . . .
I7 I 0.32902(3) 0.50966(3) 0.26290(4) 0.02747(12) Uani 1 1 d . . . . .
I1 I 0.80653(3) 0.50468(3) 0.50172(4) 0.02764(12) Uani 1 1 d . . . . .
I5 I 0.55739(3) 0.50493(3) 0.36852(5) 0.02777(12) Uani 1 1 d . . . . .
I4 I 0.56523(3) 0.67613(3) 0.60176(5) 0.02895(12) Uani 1 1 d . . . . .
I6 I 0.45374(3) 0.69839(3) 0.25605(5) 0.03159(13) Uani 1 1 d . . . . .
I9 I 0.22094(3) 0.70141(3) 0.13296(5) 0.03117(13) Uani 1 1 d . . . . .
I11 I 0.09526(3) 0.68665(3) 0.36379(5) 0.03101(13) Uani 1 1 d . . . . .
I3 I 0.68517(3) 0.67327(3) 0.33686(5) 0.03256(13) Uani 1 1 d . . . . .
I2 I 0.79363(3) 0.67801(3) 0.69360(5) 0.03759(15) Uani 1 1 d . . . . .
I10 I 0.08474(4) 0.53190(3) 0.12598(5) 0.03738(15) Uani 1 1 d . . . . .
O3 O -0.0524(3) 0.6011(3) 0.4196(5) 0.0318(14) Uani 1 1 d . . . . .
O4 O -0.0423(4) 0.7361(3) 0.4710(5) 0.0383(15) Uani 1 1 d . . . . .
N1 N 0.6528(6) 0.4793(4) 0.0672(7) 0.050(2) Uani 1 1 d . . . . .
H1 H 0.650423 0.518496 0.034023 0.060 Uiso 1 1 calc R . . . .
O1 O 0.6085(5) 0.5990(4) -0.0434(7) 0.064(2) Uani 1 1 d . . . . .
N2 N 0.0383(4) 0.6292(4) 0.6268(6) 0.0362(18) Uani 1 1 d . . . . .
H2A H 0.019990 0.628973 0.553027 0.043 Uiso 1 1 calc R . . . .
C1 C 0.6782(6) 0.4755(5) 0.1782(9) 0.041(2) Uani 1 1 d . . . . .
H1A H 0.693686 0.515106 0.220834 0.049 Uiso 1 1 calc R . . . .
O2 O 0.7480(5) 0.5880(4) 0.0697(7) 0.065(2) Uani 1 1 d . . . . .
C17 C -0.1043(5) 0.6473(5) 0.3544(7) 0.035(2) Uani 1 1 d . . . . .
H17A H -0.151466 0.624920 0.323238 0.042 Uiso 1 1 calc R . . . .
H17B H -0.088609 0.665034 0.291190 0.042 Uiso 1 1 calc R . . . .
C3 C 0.6599(5) 0.3588(4) 0.1701(8) 0.034(2) Uani 1 1 d . . . . .
H3 H 0.661151 0.316509 0.205678 0.041 Uiso 1 1 calc R . . . .
C11 C 0.1367(6) 0.6405(5) 0.7868(8) 0.042(2) Uani 1 1 d . . . . .
H11 H 0.186428 0.649420 0.820347 0.050 Uiso 1 1 calc R . . . .
C16 C -0.1102(5) 0.7027(5) 0.4319(8) 0.038(2) Uani 1 1 d . . . . .
H16A H -0.147821 0.734835 0.391587 0.046 Uiso 1 1 calc R . . . .
H16B H -0.123897 0.684362 0.496594 0.046 Uiso 1 1 calc R . . . .
C12 C 0.0938(6) 0.6264(5) 0.8532(7) 0.041(2) Uani 1 1 d . . . . .
H12 H 0.113832 0.624427 0.932693 0.049 Uiso 1 1 calc R . . . .
C10 C 0.1083(5) 0.6420(4) 0.6722(8) 0.036(2) Uani 1 1 d . . . . .
H10 H 0.137847 0.651928 0.625664 0.044 Uiso 1 1 calc R . . . .
C4 C 0.6350(6) 0.3646(5) 0.0542(8) 0.047(3) Uani 1 1 d . . . . .
H4 H 0.620778 0.325692 0.008979 0.056 Uiso 1 1 calc R . . . .
C13 C 0.0208(6) 0.6147(4) 0.8037(8) 0.038(2) Uani 1 1 d . . . . .
H13 H -0.010481 0.605670 0.847883 0.045 Uiso 1 1 calc R . . . .
C2 C 0.6826(5) 0.4156(5) 0.2324(8) 0.038(2) Uani 1 1 d . . . . .
H2 H 0.701142 0.413288 0.312076 0.046 Uiso 1 1 calc R . . . .
C18 C -0.0411(6) 0.5473(5) 0.3512(8) 0.041(2) Uani 1 1 d . . . . .
H18A H -0.032851 0.565446 0.282837 0.062 Uiso 1 1 calc GR . . . .
H18B H -0.083729 0.518381 0.330451 0.062 Uiso 1 1 calc GR . . . .
H18C H 0.000887 0.521211 0.393265 0.062 Uiso 1 1 calc GR . . . .
C14 C -0.0039(6) 0.6169(5) 0.6899(9) 0.044(2) Uani 1 1 d . . . . .
H14 H -0.053641 0.609298 0.654094 0.053 Uiso 1 1 calc R . . . .
C8 C 0.6514(8) 0.6554(5) -0.0145(10) 0.059(3) Uani 1 1 d . . . . .
H8A H 0.649974 0.672367 0.059563 0.071 Uiso 1 1 calc R . . . .
H8B H 0.633158 0.690990 -0.071231 0.071 Uiso 1 1 calc R . . . .
C5 C 0.6308(7) 0.4250(5) 0.0053(9) 0.055(3) Uani 1 1 d . . . . .
H5 H 0.612025 0.428866 -0.074220 0.066 Uiso 1 1 calc R . . . .
C7 C 0.7285(8) 0.6376(6) -0.0093(11) 0.070(4) Uani 1 1 d . . . . .
H7A H 0.730942 0.621504 -0.083373 0.083 Uiso 1 1 calc R . . . .
H7B H 0.760436 0.676943 0.013405 0.083 Uiso 1 1 calc R . . . .
C6 C 0.8116(8) 0.5605(8) 0.0648(12) 0.080(4) Uani 1 1 d . . . . .
H6A H 0.809345 0.552846 -0.013972 0.120 Uiso 1 1 calc GR . . . .
H6B H 0.819623 0.517812 0.105550 0.120 Uiso 1 1 calc GR . . . .
H6C H 0.851225 0.591258 0.099524 0.120 Uiso 1 1 calc GR . . . .
C9 C 0.5352(9) 0.6080(7) -0.0530(14) 0.087(5) Uani 1 1 d . . . . .
H9A H 0.518027 0.649655 -0.093980 0.131 Uiso 1 1 calc GR . . . .
H9B H 0.529035 0.610612 0.022339 0.131 Uiso 1 1 calc GR . . . .
H9C H 0.507402 0.570165 -0.094029 0.131 Uiso 1 1 calc GR . . . .
C15 C -0.0448(7) 0.7913(6) 0.5413(9) 0.055(3) Uani 1 1 d . . . . .
H15A H -0.076781 0.825784 0.497215 0.083 Uiso 1 1 calc GR . . . .
H15B H 0.003707 0.809854 0.572562 0.083 Uiso 1 1 calc GR . . . .
H15C H -0.062958 0.776432 0.602938 0.083 Uiso 1 1 calc GR . . . .


_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
Bi3 I8 3.3656(6) . ?
Bi3 I7 3.3306(6) . ?
Bi3 I1 3.4039(6) 3_666 ?
Bi3 I9 2.8821(6) . ?
Bi3 I11 2.8765(6) . ?
Bi3 I10 2.9057(7) . ?
Bi1 I7 3.4015(6) 3_666 ?
Bi1 I1 3.0224(6) . ?
Bi1 I5 3.3207(7) . ?
Bi1 I4 3.2275(6) . ?
Bi1 I3 2.8656(6) . ?
Bi1 I2 2.8869(7) . ?
Bi2 I8 2.9942(6) . ?
Bi2 I7 3.1909(6) . ?
Bi2 I5 3.1856(6) . ?
Bi2 I5 3.3708(6) 3_666 ?
Bi2 I4 3.0257(6) . ?
Bi2 I6 2.8677(6) . ?
O3 C17 1.430(10) . ?
O3 C18 1.427(11) . ?
O4 C16 1.430(11) . ?
O4 C15 1.417(11) . ?
N1 C1 1.323(13) . ?
N1 C5 1.325(13) . ?
O1 C8 1.384(13) . ?
O1 C9 1.407(17) . ?
N2 C10 1.335(12) . ?
N2 C14 1.316(12) . ?
C1 C2 1.361(13) . ?
O2 C7 1.366(14) . ?
O2 C6 1.370(16) . ?
C17 C16 1.493(13) . ?
C3 C4 1.382(13) . ?
C3 C2 1.371(13) . ?
C11 C12 1.366(13) . ?
C11 C10 1.367(13) . ?
C12 C13 1.391(14) . ?
C4 C5 1.342(14) . ?
C13 C14 1.353(13) . ?
C8 C7 1.524(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I8 Bi3 I1 83.789(15) . 3_666 ?
I7 Bi3 I8 82.357(15) . . ?
I7 Bi3 I1 83.676(15) . 3_666 ?
I9 Bi3 I8 88.732(17) . . ?
I9 Bi3 I7 90.807(17) . . ?
I9 Bi3 I1 171.227(19) . 3_666 ?
I9 Bi3 I10 95.473(19) . . ?
I11 Bi3 I8 88.740(17) . . ?
I11 Bi3 I7 168.339(19) . . ?
I11 Bi3 I1 87.902(17) . 3_666 ?
I11 Bi3 I9 96.534(19) . . ?
I11 Bi3 I10 94.30(2) . . ?
I10 Bi3 I8 174.492(19) . . ?
I10 Bi3 I7 94.002(18) . . ?
I10 Bi3 I1 91.723(17) . 3_666 ?
I1 Bi1 I7 88.539(16) . 3_666 ?
I1 Bi1 I5 93.767(16) . . ?
I1 Bi1 I4 170.092(18) . . ?
I5 Bi1 I7 83.298(15) . 3_666 ?
I4 Bi1 I7 81.573(16) . 3_666 ?
I4 Bi1 I5 85.740(16) . . ?
I3 Bi1 I7 170.172(19) . 3_666 ?
I3 Bi1 I1 92.939(18) . . ?
I3 Bi1 I5 86.909(18) . . ?
I3 Bi1 I4 96.913(18) . . ?
I3 Bi1 I2 97.07(2) . . ?
I2 Bi1 I7 92.588(18) . 3_666 ?
I2 Bi1 I1 92.014(19) . . ?
I2 Bi1 I5 172.810(19) . . ?
I2 Bi1 I4 87.830(18) . . ?
I8 Bi2 I7 90.873(17) . . ?
I8 Bi2 I5 85.592(16) . 3_666 ?
I8 Bi2 I5 170.262(18) . . ?
I8 Bi2 I4 92.969(17) . . ?
I7 Bi2 I5 85.778(15) . 3_666 ?
I5 Bi2 I7 83.469(16) . . ?
I5 Bi2 I5 86.091(15) . 3_666 ?
I4 Bi2 I7 171.456(18) . . ?
I4 Bi2 I5 86.912(16) . 3_666 ?
I4 Bi2 I5 91.631(17) . . ?
I6 Bi2 I8 95.642(18) . . ?
I6 Bi2 I7 95.671(18) . . ?
I6 Bi2 I5 92.807(18) . . ?
I6 Bi2 I5 178.07(2) . 3_666 ?
I6 Bi2 I4 91.544(18) . . ?
Bi2 I8 Bi3 93.886(16) . . ?
Bi3 I7 Bi1 91.082(15) . 3_666 ?
Bi2 I7 Bi3 91.035(15) . . ?
Bi2 I7 Bi1 96.157(16) . 3_666 ?
Bi1 I1 Bi3 96.616(16) . 3_666 ?
Bi1 I5 Bi2 94.333(16) . 3_666 ?
Bi2 I5 Bi1 88.546(15) . . ?
Bi2 I5 Bi2 93.909(15) . 3_666 ?
Bi2 I4 Bi1 93.131(16) . . ?
C18 O3 C17 110.8(7) . . ?
C15 O4 C16 112.0(8) . . ?
C1 N1 C5 121.1(9) . . ?
C8 O1 C9 115.8(10) . . ?
C14 N2 C10 121.5(8) . . ?
N1 C1 C2 121.0(9) . . ?
C7 O2 C6 108.7(11) . . ?
O3 C17 C16 106.8(7) . . ?
C2 C3 C4 118.3(9) . . ?
C12 C11 C10 120.2(10) . . ?
O4 C16 C17 108.9(7) . . ?
C11 C12 C13 119.7(8) . . ?
N2 C10 C11 118.9(9) . . ?
C5 C4 C3 120.2(10) . . ?
C14 C13 C12 117.1(9) . . ?
C1 C2 C3 119.0(9) . . ?
N2 C14 C13 122.6(10) . . ?
O1 C8 C7 109.4(9) . . ?
N1 C5 C4 120.4(10) . . ?
O2 C7 C8 105.1(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound1_100K
_database_code_depnum_ccdc_archive 'CCDC 2025570'
loop_
_audit_author_name
_audit_author_address
'Jakob Moebs'
;Philipps University Marburg
Germany
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10.8 Bi3 Cu1.2 I12 N2, C5 H6 N'
_chemical_formula_sum            'C15 H16.80 Bi3 Cu1.20 I12 N3'
_chemical_formula_weight         2465.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9152(5)
_cell_length_b                   10.0648(5)
_cell_length_c                   11.4957(6)
_cell_angle_alpha                64.8710(10)
_cell_angle_beta                 78.306(2)
_cell_angle_gamma                85.680(2)
_cell_volume                     1017.00(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.660
_shelx_estimated_absorpt_T_min   0.316
_exptl_absorpt_coefficient_mu    22.676
_exptl_absorpt_correction_T_max  0.0915
_exptl_absorpt_correction_T_min  0.0557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.6087.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    4.025
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.066
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            39268
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.314
_diffrn_reflns_theta_min         2.235
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2970
_reflns_number_total             3686
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.114
_refine_diff_density_min         -1.406
_refine_diff_density_rms         0.246
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0094P)²+15.5627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: Cu1(0.6) H1(0.4) N2(0.5) H2A(0.5) C10(0.5) H10(0.5) C9(0.5)
 H9(0.5) C8(0.5) H8(0.5) C7(0.5) H7(0.5) C6(0.5) H6(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C1(H1A), C2(H2), C5(H5), C4(H4), N2(H2A), C10(H10), C9(H9),
 C8(H8), C7(H7), C6(H6)
3.b Fitted hexagon refined as free rotating group:
 N2(C10,C9,C8,C7,C6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.88581(4) 0.55848(4) 0.33732(4) 0.01568(10) Uani 1 1 d . . . . .
Bi2 Bi 1.0000 1.0000 0.0000 0.02265(15) Uani 1 2 d S T P A .
I1 I 0.90704(7) 0.90696(7) 0.29673(6) 0.01640(16) Uani 1 1 d . . . . .
I3 I 0.79748(7) 0.44479(7) 0.63330(6) 0.01786(16) Uani 1 1 d . . . . .
I5 I 0.99249(7) 0.68008(7) 0.03450(7) 0.01840(16) Uani 1 1 d . . . . .
I6 I 0.69690(7) 1.02994(8) -0.02423(7) 0.02309(17) Uani 1 1 d . . . . .
I2 I 0.59703(7) 0.61384(7) 0.30643(7) 0.02063(16) Uani 1 1 d . . . . .
I4 I 0.90349(8) 0.26940(7) 0.34520(7) 0.02257(17) Uani 1 1 d . . . . .
Cu1 Cu 0.6652(2) 0.8900(2) 0.2330(2) 0.0230(5) Uani 0.6 1 d . . . A 1
N1 N 0.5189(10) 0.9901(10) 0.3136(9) 0.028(2) Uani 1 1 d . . . . .
H1 H 0.5831 0.9317 0.2974 0.033 Uiso 0.4 1 calc R . . A 2
C3 C 0.3155(12) 1.1691(12) 0.3644(11) 0.033(3) Uani 1 1 d . . . . .
H3 H 0.2456 1.2331 0.3793 0.040 Uiso 1 1 calc R . . . .
C1 C 0.3841(12) 0.9598(12) 0.3284(11) 0.028(3) Uani 1 1 d . . . . .
H1A H 0.3596 0.8744 0.3214 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2814(11) 1.0499(13) 0.3534(10) 0.026(3) Uani 1 1 d . . . . .
H2 H 0.1875 1.0272 0.3627 0.031 Uiso 1 1 calc R . . . .
C5 C 0.5522(13) 1.1078(14) 0.3239(12) 0.038(3) Uani 1 1 d . . . . .
H5 H 0.6470 1.1305 0.3103 0.045 Uiso 1 1 calc R . . . .
C4 C 0.4550(14) 1.2006(13) 0.3538(12) 0.038(3) Uani 1 1 d . . . . .
H4 H 0.4811 1.2816 0.3666 0.046 Uiso 1 1 calc R . . . .
N2 N 0.3983(17) 1.6200(16) 0.0145(17) 0.043(6) Uiso 0.5 1 d . . . B -1
H2A H 0.3328 1.6798 0.0258 0.051 Uiso 0.5 1 calc R . . B -1
C10 C 0.3643(17) 1.4852(18) 0.0210(18) 0.024(5) Uiso 0.5 1 d G . . B -1
H10 H 0.2704 1.4577 0.0378 0.029 Uiso 0.5 1 calc R . . B -1
C9 C 0.468(2) 1.3907(16) 0.003(2) 0.056(9) Uiso 0.5 1 d G . . B -1
H9 H 0.4445 1.2986 0.0076 0.068 Uiso 0.5 1 calc R . . B -1
C8 C 0.6052(19) 1.4310(19) -0.021(2) 0.046(8) Uiso 0.5 1 d G . . B -1
H8 H 0.6759 1.3665 -0.0335 0.056 Uiso 0.5 1 calc R . . B -1
C7 C 0.6392(16) 1.566(2) -0.028(2) 0.050(8) Uiso 0.5 1 d G . . B -1
H7 H 0.7331 1.5934 -0.0446 0.060 Uiso 0.5 1 calc R . . B -1
C6 C 0.5358(19) 1.6603(15) -0.0099(19) 0.035(6) Uiso 0.5 1 d G . . B -1
H6 H 0.5590 1.7525 -0.0144 0.043 Uiso 0.5 1 calc R . . B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I1 3.3534(7) . ?
Bi1 I3 3.0479(8) . ?
Bi1 I3 3.2220(8) 2_766 ?
Bi1 I5 3.1336(8) . ?
Bi1 I2 2.9391(8) . ?
Bi1 I4 2.8654(8) . ?
Bi2 I1 3.0830(7) 2_775 ?
Bi2 I1 3.0830(7) . ?
Bi2 I5 3.0774(7) 2_775 ?
Bi2 I5 3.0774(7) . ?
Bi2 I6 3.0549(7) 2_775 ?
Bi2 I6 3.0549(7) . ?
I1 Cu1 2.683(2) . ?
I3 Bi1 3.2220(8) 2_766 ?
I6 Cu1 2.642(2) . ?
I2 Cu1 2.637(2) . ?
Cu1 N1 2.001(9) . ?
N1 C1 1.354(14) . ?
N1 C5 1.312(15) . ?
C3 C2 1.332(16) . ?
C3 C4 1.412(17) . ?
C1 C2 1.380(15) . ?
C5 C4 1.386(17) . ?
N2 C10 1.3900 . ?
N2 C6 1.3900 . ?
C10 C9 1.3900 . ?
C9 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?

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
I3 Bi1 I1 82.320(18) 2_766 . ?
I3 Bi1 I1 92.875(19) . . ?
I3 Bi1 I3 89.64(2) . 2_766 ?
I3 Bi1 I5 176.82(2) . . ?
I5 Bi1 I1 85.840(19) . . ?
I5 Bi1 I3 87.31(2) . 2_766 ?
I2 Bi1 I1 87.76(2) . . ?
I2 Bi1 I3 170.06(2) . 2_766 ?
I2 Bi1 I3 90.40(2) . . ?
I2 Bi1 I5 92.45(2) . . ?
I4 Bi1 I1 171.84(2) . . ?
I4 Bi1 I3 93.16(2) . . ?
I4 Bi1 I3 92.24(2) . 2_766 ?
I4 Bi1 I5 87.85(2) . . ?
I4 Bi1 I2 97.68(2) . . ?
I1 Bi2 I1 180.0 2_775 . ?
I5 Bi2 I1 91.704(17) . . ?
I5 Bi2 I1 88.296(17) . 2_775 ?
I5 Bi2 I1 91.704(17) 2_775 2_775 ?
I5 Bi2 I1 88.296(17) 2_775 . ?
I5 Bi2 I5 180.0 . 2_775 ?
I6 Bi2 I1 88.479(19) 2_775 2_775 ?
I6 Bi2 I1 91.522(19) 2_775 . ?
I6 Bi2 I1 91.522(19) . 2_775 ?
I6 Bi2 I1 88.478(19) . . ?
I6 Bi2 I5 89.61(2) 2_775 2_775 ?
I6 Bi2 I5 90.39(2) . 2_775 ?
I6 Bi2 I5 89.61(2) . . ?
I6 Bi2 I5 90.39(2) 2_775 . ?
I6 Bi2 I6 180.0 . 2_775 ?
Bi2 I1 Bi1 89.055(17) . . ?
Cu1 I1 Bi1 75.46(5) . . ?
Cu1 I1 Bi2 80.09(5) . . ?
Bi1 I3 Bi1 90.36(2) . 2_766 ?
Bi2 I5 Bi1 93.327(19) . . ?
Cu1 I6 Bi2 81.24(5) . . ?
Cu1 I2 Bi1 83.82(5) . . ?
I6 Cu1 I1 107.06(8) . . ?
I2 Cu1 I1 110.52(8) . . ?
I2 Cu1 I6 109.32(8) . . ?
N1 Cu1 I1 110.2(3) . . ?
N1 Cu1 I6 108.7(3) . . ?
N1 Cu1 I2 111.0(3) . . ?
C1 N1 Cu1 120.4(7) . . ?
C5 N1 Cu1 118.8(8) . . ?
C5 N1 C1 119.0(10) . . ?
C2 C3 C4 120.2(11) . . ?
N1 C1 C2 121.6(10) . . ?
C3 C2 C1 119.3(10) . . ?
N1 C5 C4 122.8(12) . . ?
C5 C4 C3 116.9(11) . . ?
C10 N2 C6 120.0 . . ?
N2 C10 C9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C7 C6 N2 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 2025575'
loop_
_audit_author_name
_audit_author_address
'Jakob Moebs'
;Philipps University Marburg
Germany
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2019-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I7, C4 H10 O2, C5 H6 N'
_chemical_formula_sum            'C9 H16 Bi2 I7 N O2'
_chemical_formula_weight         1476.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7505(7)
_cell_length_b                   11.6799(8)
_cell_length_c                   13.0200(13)
_cell_angle_alpha                102.317(7)
_cell_angle_beta                 111.546(7)
_cell_angle_gamma                109.350(5)
_cell_volume                     1326.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    34488
_cell_measurement_temperature    100
_cell_measurement_theta_max      54.1
_cell_measurement_theta_min      3.6
_shelx_estimated_absorpt_T_max   0.408
_shelx_estimated_absorpt_T_min   0.145
_exptl_absorpt_coefficient_mu    21.403
_exptl_absorpt_correction_T_max  0.3634
_exptl_absorpt_correction_T_min  0.0560
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-Red32 1.63.4'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34488
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.895
_diffrn_reflns_theta_min         1.819
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       'area detetor, ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4347
_reflns_number_total             5671
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.313
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.239
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         5671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0176P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0482
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C3(H3), C2(H2), C1(H1A), C5(H5)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.10190(3) -0.28019(2) 0.06768(2) 0.01734(7) Uani 1 1 d . . . . .
Bi2 Bi 0.26842(3) 0.16125(3) 0.13963(2) 0.01773(7) Uani 1 1 d . . . . .
I4 I -0.01010(4) -0.07915(4) 0.14603(4) 0.01864(10) Uani 1 1 d . . . . .
I1 I 0.17062(5) -0.48901(4) -0.05522(4) 0.02035(10) Uani 1 1 d . . . . .
I7 I 0.16234(5) 0.35490(5) 0.21049(4) 0.02200(10) Uani 1 1 d . . . . .
I3 I 0.33648(5) -0.07903(4) 0.04325(4) 0.02076(10) Uani 1 1 d . . . . .
I5 I 0.47902(5) 0.31213(4) 0.07772(4) 0.02214(10) Uani 1 1 d . . . . .
I2 I 0.29787(5) -0.23403(5) 0.30819(4) 0.02711(11) Uani 1 1 d . . . . .
I6 I 0.47849(5) 0.24149(5) 0.38608(4) 0.02778(12) Uani 1 1 d . . . . .
O1 O 1.1168(5) 0.7181(5) 0.6102(4) 0.0311(12) Uani 1 1 d . . . . .
O2 O 1.1446(5) 0.9465(5) 0.5617(4) 0.0283(12) Uani 1 1 d . . . . .
N1 N 0.8571(6) 0.6883(6) 0.4343(5) 0.0260(14) Uani 1 1 d . . . . .
H1 H 0.943522 0.702414 0.490682 0.031 Uiso 1 1 calc R . . . .
C4 C 0.7201(8) 0.6984(7) 0.2540(6) 0.0278(17) Uani 1 1 d . . . . .
H4 H 0.715600 0.720050 0.186783 0.033 Uiso 1 1 calc R . . . .
C3 C 0.5921(8) 0.6445(7) 0.2625(6) 0.0303(17) Uani 1 1 d . . . . .
H3 H 0.499134 0.630654 0.202330 0.036 Uiso 1 1 calc R . . . .
C2 C 0.5984(8) 0.6103(7) 0.3586(6) 0.0312(18) Uani 1 1 d . . . . .
H2 H 0.510238 0.570538 0.364925 0.037 Uiso 1 1 calc R . . . .
C6 C 1.1785(8) 1.0194(7) 0.4925(6) 0.0287(17) Uani 1 1 d . . . . .
H6A H 1.200522 0.970450 0.436041 0.043 Uiso 1 1 calc GR . . . .
H6B H 1.265934 1.104536 0.545543 0.043 Uiso 1 1 calc GR . . . .
H6C H 1.092461 1.033136 0.448296 0.043 Uiso 1 1 calc GR . . . .
C7 C 1.2699(8) 0.9318(8) 0.6336(7) 0.0359(19) Uani 1 1 d . . . . .
H7A H 1.352110 1.018992 0.692576 0.043 Uiso 1 1 calc R . . . .
H7B H 1.306060 0.892519 0.582595 0.043 Uiso 1 1 calc R . . . .
C1 C 0.7348(9) 0.6352(7) 0.4445(6) 0.0309(18) Uani 1 1 d . . . . .
H1A H 0.742206 0.614218 0.512379 0.037 Uiso 1 1 calc R . . . .
C5 C 0.8540(8) 0.7211(7) 0.3415(6) 0.0278(17) Uani 1 1 d . . . . .
H5 H 0.943523 0.759639 0.336681 0.033 Uiso 1 1 calc R . . . .
C8 C 1.2282(8) 0.8468(8) 0.6965(6) 0.0339(19) Uani 1 1 d . . . . .
H8A H 1.317650 0.841999 0.750690 0.041 Uiso 1 1 calc R . . . .
H8B H 1.188177 0.883921 0.745159 0.041 Uiso 1 1 calc R . . . .
C9 C 1.1078(9) 0.6210(8) 0.6606(7) 0.039(2) Uani 1 1 d . . . . .
H9A H 1.017883 0.538756 0.603711 0.058 Uiso 1 1 calc GR . . . .
H9B H 1.102343 0.650711 0.734481 0.058 Uiso 1 1 calc GR . . . .
H9C H 1.196798 0.606396 0.678506 0.058 Uiso 1 1 calc GR . . . .


_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 3.1238(6) . ?
Bi1 I1 3.1793(5) 2_545 ?
Bi1 I1 3.0744(6) . ?
Bi1 I7 3.3765(6) 2 ?
Bi1 I3 2.9937(5) . ?
Bi1 I2 2.8665(6) . ?
Bi2 I4 3.4012(5) . ?
Bi2 I4 3.4046(6) 2 ?
Bi2 I7 2.9764(6) . ?
Bi2 I3 3.2433(6) . ?
Bi2 I5 2.8607(5) . ?
Bi2 I6 2.8752(6) . ?
O1 C8 1.433(9) . ?
O1 C9 1.421(8) . ?
O2 C6 1.425(7) . ?
O2 C7 1.419(8) . ?
N1 C1 1.324(9) . ?
N1 C5 1.336(8) . ?
C4 C3 1.367(10) . ?
C4 C5 1.362(9) . ?
C3 C2 1.378(9) . ?
C2 C1 1.363(10) . ?
C7 C8 1.476(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I4 Bi1 I1 90.402(14) . 2_545 ?
I4 Bi1 I7 84.528(15) . 2 ?
I1 Bi1 I4 169.692(13) . . ?
I1 Bi1 I1 88.359(15) . 2_545 ?
I1 Bi1 I7 85.172(15) . 2 ?
I1 Bi1 I7 80.894(15) 2_545 2 ?
I3 Bi1 I4 91.876(14) . . ?
I3 Bi1 I1 172.247(14) . 2_545 ?
I3 Bi1 I1 88.076(15) . . ?
I3 Bi1 I7 91.945(15) . 2 ?
I2 Bi1 I4 93.782(16) . . ?
I2 Bi1 I1 92.604(17) . 2_545 ?
I2 Bi1 I1 96.496(17) . . ?
I2 Bi1 I7 173.255(15) . 2 ?
I2 Bi1 I3 94.638(18) . . ?
I4 Bi2 I4 85.307(15) . 2 ?
I7 Bi2 I4 90.646(15) . . ?
I7 Bi2 I4 86.313(15) . 2 ?
I7 Bi2 I3 172.204(14) . . ?
I3 Bi2 I4 88.894(15) . 2 ?
I3 Bi2 I4 82.829(14) . . ?
I5 Bi2 I4 84.904(15) . 2 ?
I5 Bi2 I4 165.256(15) . . ?
I5 Bi2 I7 99.692(16) . . ?
I5 Bi2 I3 85.984(15) . . ?
I5 Bi2 I6 96.199(17) . . ?
I6 Bi2 I4 176.202(16) . 2 ?
I6 Bi2 I4 94.284(17) . . ?
I6 Bi2 I7 89.917(17) . . ?
I6 Bi2 I3 94.804(16) . . ?
Bi1 I4 Bi2 92.928(15) . 2 ?
Bi1 I4 Bi2 89.813(14) . . ?
Bi2 I4 Bi2 94.692(15) . 2 ?
Bi1 I1 Bi1 91.642(15) . 2_545 ?
Bi2 I7 Bi1 96.218(16) . 2 ?
Bi1 I3 Bi2 95.247(15) . . ?
C9 O1 C8 112.3(5) . . ?
C7 O2 C6 111.4(5) . . ?
C1 N1 C5 122.3(6) . . ?
C5 C4 C3 120.2(6) . . ?
C4 C3 C2 119.8(6) . . ?
C1 C2 C3 118.1(7) . . ?
O2 C7 C8 110.3(6) . . ?
N1 C1 C2 120.8(6) . . ?
N1 C5 C4 118.8(7) . . ?
O1 C8 C7 109.0(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound1_293K
_database_code_depnum_ccdc_archive 'CCDC 2025571'
loop_
_audit_author_name
_audit_author_address
'Jakob Moebs'
;Philipps University Marburg
Germany
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;
_audit_creation_date             2020-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 Bi3 Cu I12 N2, C5 H6 N'
_chemical_formula_sum            'C15 H17 Bi3 Cu I12 N3'
_chemical_formula_weight         2452.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9874(6)
_cell_length_b                   10.1149(6)
_cell_length_c                   11.6385(7)
_cell_angle_alpha                65.080(2)
_cell_angle_beta                 78.747(2)
_cell_angle_gamma                86.282(2)
_cell_volume                     1045.58(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8017
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.383
_shelx_estimated_absorpt_T_min   0.056
_exptl_absorpt_coefficient_mu    21.957
_exptl_absorpt_correction_T_max  0.0185
_exptl_absorpt_correction_T_min  0.0029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1429 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.1568.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    3.895
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1042
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21510
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.287
_diffrn_reflns_theta_min         2.221
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'area detetor, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3017
_reflns_number_total             3774
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.002
_refine_diff_density_min         -1.598
_refine_diff_density_rms         0.226
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3774
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+18.5662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1195
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C10 \\sim C9 \\sim C8 \\sim C7 \\sim C6 \\sim N2: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 C10, C9, C8, C7, C6, N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: Cu1(0.5) H1(0.5) C10(0.5) H10(0.5) C9(0.5) H9(0.5) C8(0.5) H8(0.5)
 C7(0.5) H7(0.5) C6(0.5) H6(0.5) N2(0.5) H2A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C4(H4), C3(H3), C2(H2), C1(H1A), C10(H10), C9(H9), C8(H8),
 C7(H7), C6(H6), N2(H2A)
5.b Fitted hexagon refined as free rotating group:
 N1(C5,C4,C3,C2,C1), C10(C9,C8,C7,C6,N2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.38510(6) 0.55894(6) 0.33713(6) 0.05017(19) Uani 1 1 d . . . . .
Bi2 Bi 0.5000 1.0000 0.0000 0.0557(2) Uani 1 2 d S T P A .
I1 I 0.40982(11) 0.90780(11) 0.29352(11) 0.0548(3) Uani 1 1 d . . . . .
I2 I 0.29976(11) 0.44577(13) 0.62965(11) 0.0577(3) Uani 1 1 d . . . . .
I3 I 0.49077(12) 0.67990(11) 0.03710(11) 0.0577(3) Uani 1 1 d . . . . .
I4 I 0.19863(11) 1.02748(14) -0.02380(12) 0.0672(3) Uani 1 1 d . . . . .
I5 I 0.09837(11) 0.61059(14) 0.30809(13) 0.0668(3) Uani 1 1 d . . . . .
I6 I 0.40164(14) 0.27207(13) 0.34290(13) 0.0710(4) Uani 1 1 d . . . . .
Cu1 Cu 0.1623(5) 0.8921(5) 0.2295(5) 0.0712(12) Uani 0.5 1 d . . . A 1
N1 N 0.0204(12) 0.9952(15) 0.3079(13) 0.090(5) Uani 1 1 d . . . . .
H1 H 0.0824 0.9410 0.2887 0.108 Uiso 0.5 1 calc R . . A 2
C5 C 0.0572(13) 1.1178(17) 0.3207(15) 0.102(8) Uani 1 1 d G . . A .
H5 H 0.1489 1.1412 0.3086 0.123 Uiso 1 1 calc R . . . .
C4 C -0.0431(19) 1.2055(14) 0.3516(16) 0.101(8) Uani 1 1 d G . . A .
H4 H -0.0185 1.2875 0.3602 0.121 Uiso 1 1 calc R . . . .
C3 C -0.1802(17) 1.1706(16) 0.3697(16) 0.102(8) Uani 1 1 d G . . A .
H3 H -0.2473 1.2292 0.3904 0.122 Uiso 1 1 calc R . . . .
C2 C -0.2170(10) 1.0480(17) 0.3569(15) 0.095(7) Uani 1 1 d G . . A .
H2 H -0.3088 1.0246 0.3690 0.114 Uiso 1 1 calc R . . . .
C1 C -0.1167(14) 0.9603(13) 0.3259(14) 0.078(5) Uani 1 1 d G . . A .
H1A H -0.1414 0.8783 0.3174 0.094 Uiso 1 1 calc R . . . .
C10 C -0.115(3) 1.440(5) 0.015(4) 0.097(10) Uani 0.5 1 d . U . B -1
H10 H -0.2059 1.4110 0.0309 0.117 Uiso 0.5 1 calc R . . B -1
C9 C -0.011(5) 1.349(4) -0.005(5) 0.097(10) Uani 0.5 1 d G U . B -1
H9 H -0.0328 1.2595 -0.0023 0.117 Uiso 0.5 1 calc R . . B -1
C8 C 0.124(4) 1.392(5) -0.028(5) 0.104(11) Uani 0.5 1 d G U . B -1
H8 H 0.1938 1.3309 -0.0416 0.124 Uiso 0.5 1 calc R . . B -1
C7 C 0.157(3) 1.525(6) -0.032(5) 0.106(11) Uani 0.5 1 d G U . B -1
H7 H 0.2474 1.5538 -0.0477 0.127 Uiso 0.5 1 calc R . . B -1
C6 C 0.053(4) 1.616(5) -0.012(5) 0.107(11) Uani 0.5 1 d G U . B -1
H6 H 0.0743 1.7054 -0.0146 0.129 Uiso 0.5 1 calc R . . B -1
N2 N -0.083(4) 1.573(5) 0.011(4) 0.105(10) Uani 0.5 1 d G U . B -1
H2A H -0.1471 1.6294 0.0237 0.126 Uiso 0.5 1 calc R . . B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I1 3.3652(12) . ?
Bi1 I2 3.0557(13) . ?
Bi1 I2 3.2401(12) 2_666 ?
Bi1 I3 3.1517(13) . ?
Bi1 I5 2.9364(13) . ?
Bi1 I6 2.8687(13) . ?
Bi2 I1 3.0942(11) 2_675 ?
Bi2 I1 3.0942(11) . ?
Bi2 I3 3.0860(10) . ?
Bi2 I3 3.0860(10) 2_675 ?
Bi2 I4 3.0603(11) . ?
Bi2 I4 3.0603(11) 2_675 ?
I1 Cu1 2.750(5) . ?
I2 Bi1 3.2401(12) 2_666 ?
I4 Cu1 2.634(5) . ?
I5 Cu1 2.677(5) . ?
Cu1 N1 2.009(11) . ?
N1 C5 1.3900 . ?
N1 C1 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.3900 . ?
C3 C2 1.3900 . ?
C2 C1 1.3900 . ?
C10 C9 1.3900 . ?
C10 N2 1.3900 . ?
C9 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C6 N2 1.3900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 Bi1 I1 82.49(3) 2_666 . ?
I2 Bi1 I1 93.55(3) . . ?
I2 Bi1 I2 88.67(3) . 2_666 ?
I2 Bi1 I3 176.54(4) . . ?
I3 Bi1 I1 85.21(3) . . ?
I3 Bi1 I2 87.96(3) . 2_666 ?
I5 Bi1 I1 88.18(3) . . ?
I5 Bi1 I2 170.55(4) . 2_666 ?
I5 Bi1 I2 90.37(4) . . ?
I5 Bi1 I3 92.82(4) . . ?
I6 Bi1 I1 170.95(4) . . ?
I6 Bi1 I2 93.52(4) . . ?
I6 Bi1 I2 92.03(4) . 2_666 ?
I6 Bi1 I3 87.41(4) . . ?
I6 Bi1 I5 97.42(4) . . ?
I1 Bi2 I1 180.0 2_675 . ?
I3 Bi2 I1 88.83(3) 2_675 . ?
I3 Bi2 I1 91.17(3) 2_675 2_675 ?
I3 Bi2 I1 88.83(3) . 2_675 ?
I3 Bi2 I1 91.17(3) . . ?
I3 Bi2 I3 180.0 2_675 . ?
I4 Bi2 I1 91.34(3) . 2_675 ?
I4 Bi2 I1 88.66(3) . . ?
I4 Bi2 I1 88.66(3) 2_675 2_675 ?
I4 Bi2 I1 91.34(3) 2_675 . ?
I4 Bi2 I3 89.59(3) . . ?
I4 Bi2 I3 90.41(3) 2_675 . ?
I4 Bi2 I3 89.59(3) 2_675 2_675 ?
I4 Bi2 I3 90.41(3) . 2_675 ?
I4 Bi2 I4 180.0 2_675 . ?
Bi2 I1 Bi1 89.65(3) . . ?
Cu1 I1 Bi1 76.08(10) . . ?
Cu1 I1 Bi2 80.08(11) . . ?
Bi1 I2 Bi1 91.33(3) . 2_666 ?
Bi2 I3 Bi1 93.87(3) . . ?
Cu1 I4 Bi2 82.51(11) . . ?
Cu1 I5 Bi1 85.07(11) . . ?
I4 Cu1 I1 105.99(17) . . ?
I4 Cu1 I5 110.38(18) . . ?
I5 Cu1 I1 108.17(16) . . ?
N1 Cu1 I1 109.9(5) . . ?
N1 Cu1 I4 109.5(4) . . ?
N1 Cu1 I5 112.7(5) . . ?
C5 N1 Cu1 119.8(9) . . ?
C5 N1 C1 120.0 . . ?
C1 N1 Cu1 119.1(9) . . ?
C4 C5 N1 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C2 C1 N1 120.0 . . ?
C9 C10 N2 120.0 . . ?
C8 C9 C10 120.0 . . ?
C7 C8 C9 120.0 . . ?
C8 C7 C6 120.0 . . ?
N2 C6 C7 120.0 . . ?
C6 N2 C10 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
