# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_d8_5847_27mar22_ajp2_0m
_database_code_depnum_ccdc_archive 'CCDC 2182000'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(I3), C12 H10 N4 S, 2(H2 O)'
_chemical_formula_sum            'C12 H14 I6 N4 O2 S'
_chemical_formula_weight         1039.73
_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'
S S 0.1246 0.1234 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4815(4)
_cell_length_b                   32.2385(19)
_cell_length_c                   10.5446(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.562(2)
_cell_angle_gamma                90
_cell_volume                     2437.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.64
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.417
_shelx_estimated_absorpt_T_min   0.271
_exptl_absorpt_coefficient_mu    7.745
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.833
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.137
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            65198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.687
_diffrn_reflns_theta_min         2.112
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6046
_reflns_number_total             6891
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         1.103
_refine_diff_density_min         -1.312
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         6891
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0192P)²+13.1016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 H4-N4
 0.86 with sigma of 0.02
 H3-N3
 0.86 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
S1 \\sim N1: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
3.a Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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
I1 I 0.41525(5) 0.55071(2) 0.06062(3) 0.02210(7) Uani 1 1 d . . . . .
I2 I 0.49223(4) 0.63646(2) 0.15985(3) 0.01629(6) Uani 1 1 d . . . . .
I3 I 0.55480(4) 0.72125(2) 0.24676(3) 0.02143(7) Uani 1 1 d . . . . .
I4 I 0.50162(4) 0.17211(2) 0.86780(3) 0.02098(7) Uani 1 1 d . . . . .
I5 I 0.51234(4) 0.08453(2) 0.84685(3) 0.01652(6) Uani 1 1 d . . . . .
I6 I 0.53383(5) -0.00889(2) 0.80596(3) 0.02114(7) Uani 1 1 d . . . . .
S1 S 0.40506(19) 0.25356(4) 0.10650(12) 0.0234(2) Uani 1 1 d . U . . .
N1 N 0.4248(6) 0.30174(13) 0.1306(4) 0.0222(7) Uani 1 1 d . U . . .
N2 N 0.4833(5) 0.27557(11) 0.3457(4) 0.0148(7) Uani 1 1 d . . . . .
N3 N 0.5278(6) 0.43120(12) 0.4103(4) 0.0176(8) Uani 1 1 d D . . . .
H3 H 0.540(9) 0.4569(8) 0.433(6) 0.032(17) Uiso 1 1 d D . . . .
N4 N 0.5190(6) 0.12104(13) 0.4278(4) 0.0199(8) Uani 1 1 d D . . . .
H4 H 0.548(8) 0.0974(10) 0.468(5) 0.024(15) Uiso 1 1 d D . . . .
C1 C 0.4641(6) 0.30903(14) 0.2647(4) 0.0151(8) Uani 1 1 d . . . . .
C2 C 0.4883(6) 0.35197(13) 0.3175(4) 0.0147(8) Uani 1 1 d . . . . .
C3 C 0.4793(6) 0.38520(14) 0.2311(5) 0.0180(9) Uani 1 1 d . . . . .
H3A H 0.458510 0.380361 0.139108 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5007(6) 0.42498(14) 0.2800(5) 0.0182(9) Uani 1 1 d . . . . .
H4A H 0.496468 0.447845 0.222345 0.022 Uiso 1 1 calc R U . . .
C5 C 0.5378(7) 0.39981(15) 0.4961(5) 0.0202(9) Uani 1 1 d . . . . .
H5 H 0.556841 0.405576 0.587341 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5205(7) 0.35940(15) 0.4524(5) 0.0200(9) Uani 1 1 d . . . . .
H6 H 0.530286 0.337066 0.512791 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4556(6) 0.24175(14) 0.2717(4) 0.0155(8) Uani 1 1 d . . . . .
C8 C 0.4708(6) 0.19970(14) 0.3243(4) 0.0149(8) Uani 1 1 d . . . . .
C9 C 0.4820(7) 0.16561(15) 0.2445(5) 0.0206(9) Uani 1 1 d . . . . .
H9 H 0.472805 0.169441 0.153509 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5064(7) 0.12644(15) 0.2993(5) 0.0231(10) Uani 1 1 d . . . . .
H10 H 0.514391 0.103172 0.245927 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5034(7) 0.15299(15) 0.5061(5) 0.0216(9) Uani 1 1 d . . . . .
H11 H 0.509597 0.148197 0.596194 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4782(7) 0.19288(15) 0.4553(5) 0.0201(9) Uani 1 1 d . . . . .
H12 H 0.466190 0.215469 0.510132 0.024 Uiso 1 1 calc R U . . .
O1 O 0.5892(5) 0.51702(11) 0.3955(4) 0.0220(7) Uani 1 1 d G . . . .
H1A H 0.569914 0.528312 0.317826 0.033 Uiso 1 1 d G U . . .
H1B H 0.706785 0.521461 0.434531 0.033 Uiso 1 1 d G U . . .
O2 O 0.6424(5) 0.04804(10) 0.5416(3) 0.0216(7) Uani 1 1 d G . . . .
H2A H 0.605015 0.031535 0.594033 0.032 Uiso 1 1 d G U . . .
H2B H 0.678286 0.031613 0.488274 0.032 Uiso 1 1 d G U . . .


_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
I1 I2 2.9540(4) . ?
I2 I3 2.8784(5) . ?
I4 I5 2.8352(4) . ?
I5 I6 3.0530(4) . ?
S1 N1 1.574(4) . ?
S1 C7 1.716(5) . ?
N1 C1 1.380(6) . ?
N2 C1 1.358(6) . ?
N2 C7 1.323(6) . ?
N3 H3 0.860(19) . ?
N3 C4 1.346(6) . ?
N3 C5 1.345(6) . ?
N4 H4 0.868(19) . ?
N4 C10 1.343(7) . ?
N4 C11 1.346(6) . ?
C1 C2 1.484(6) . ?
C2 C3 1.396(6) . ?
C2 C6 1.394(6) . ?
C3 H3A 0.9500 . ?
C3 C4 1.374(6) . ?
C4 H4A 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.375(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.457(6) . ?
C8 C9 1.401(6) . ?
C8 C12 1.384(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.385(7) . ?
C12 H12 0.9500 . ?
O1 H1A 0.8703 . ?
O1 H1B 0.8701 . ?
O2 H2A 0.8692 . ?
O2 H2B 0.8687 . ?

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 I2 I1 177.534(15) . . ?
I4 I5 I6 175.723(14) . . ?
N1 S1 C7 94.1(2) . . ?
C1 N1 S1 108.4(3) . . ?
C7 N2 C1 108.2(4) . . ?
C4 N3 H3 114(4) . . ?
C5 N3 H3 124(4) . . ?
C5 N3 C4 122.5(4) . . ?
C10 N4 H4 122(4) . . ?
C10 N4 C11 121.8(4) . . ?
C11 N4 H4 116(4) . . ?
N1 C1 C2 120.7(4) . . ?
N2 C1 N1 117.6(4) . . ?
N2 C1 C2 121.7(4) . . ?
C3 C2 C1 119.5(4) . . ?
C6 C2 C1 120.7(4) . . ?
C6 C2 C3 119.8(4) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3A 120.2 . . ?
N3 C4 C3 119.3(4) . . ?
N3 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
N3 C5 H5 119.8 . . ?
N3 C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C2 C6 H6 120.8 . . ?
C5 C6 C2 118.5(4) . . ?
C5 C6 H6 120.8 . . ?
N2 C7 S1 111.6(3) . . ?
N2 C7 C8 124.1(4) . . ?
C8 C7 S1 124.3(3) . . ?
C9 C8 C7 120.8(4) . . ?
C12 C8 C7 120.3(4) . . ?
C12 C8 C9 118.8(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.3(5) . . ?
C10 C9 H9 120.3 . . ?
N4 C10 C9 120.3(5) . . ?
N4 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
N4 C11 H11 120.0 . . ?
N4 C11 C12 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C8 C12 C11 119.8(4) . . ?
C8 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
H1A O1 H1B 104.5 . . ?
H2A O2 H2B 104.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 N2 2.0(5) . . . . ?
S1 N1 C1 C2 -179.3(3) . . . . ?
S1 C7 C8 C9 13.1(6) . . . . ?
S1 C7 C8 C12 -168.2(4) . . . . ?
N1 S1 C7 N2 1.6(4) . . . . ?
N1 S1 C7 C8 -177.0(4) . . . . ?
N1 C1 C2 C3 -2.8(6) . . . . ?
N1 C1 C2 C6 177.4(4) . . . . ?
N2 C1 C2 C3 175.8(4) . . . . ?
N2 C1 C2 C6 -4.0(6) . . . . ?
N2 C7 C8 C9 -165.3(4) . . . . ?
N2 C7 C8 C12 13.4(7) . . . . ?
N3 C5 C6 C2 -1.5(7) . . . . ?
N4 C11 C12 C8 -0.5(7) . . . . ?
C1 N2 C7 S1 -0.7(5) . . . . ?
C1 N2 C7 C8 177.9(4) . . . . ?
C1 C2 C3 C4 179.6(4) . . . . ?
C1 C2 C6 C5 -178.5(4) . . . . ?
C2 C3 C4 N3 -0.8(7) . . . . ?
C3 C2 C6 C5 1.7(7) . . . . ?
C4 N3 C5 C6 0.1(7) . . . . ?
C5 N3 C4 C3 1.1(7) . . . . ?
C6 C2 C3 C4 -0.5(7) . . . . ?
C7 S1 N1 C1 -1.9(3) . . . . ?
C7 N2 C1 N1 -0.8(5) . . . . ?
C7 N2 C1 C2 -179.5(4) . . . . ?
C7 C8 C9 C10 176.5(4) . . . . ?
C7 C8 C12 C11 -176.3(4) . . . . ?
C8 C9 C10 N4 0.1(7) . . . . ?
C9 C8 C12 C11 2.4(7) . . . . ?
C10 N4 C11 C12 -1.6(7) . . . . ?
C11 N4 C10 C9 1.8(7) . . . . ?
C12 C8 C9 C10 -2.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT420_mo_d8_5847_27mar22_ajp2_0m 
;
PROBLEM: D-H Bond Without Acceptor  O2       --H2B      .     Please Check 
RESPONSE: These hydrogen atoms are involved in non-standard H...I hydrogen bonds
;
####################################################################### 
# 
# 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_4jul20_ajp7_xprep_a
_database_code_depnum_ccdc_archive 'CCDC 2182001'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C12 H9 N4 S, 0.5(C4 H6 N2)'
_chemical_formula_sum            'C14 H12 I N5 S'
_chemical_formula_weight         409.25
_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'
S S 0.1246 0.1234 '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                   9.8620(2)
_cell_length_b                   6.3853(2)
_cell_length_c                   25.0333(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1576.39(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.3790
_cell_measurement_theta_min      1.6210
_shelx_estimated_absorpt_T_max   0.768
_shelx_estimated_absorpt_T_min   0.680
_exptl_absorpt_coefficient_mu    2.164
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.1211
-1.00 0.00 0.00 0.0760
-2.00 1.00 1.99 0.0764
2.00 1.00 0.98 0.0954
0.00 1.00 1.98 0.0922
-2.00 0.00 1.01 0.0730
-2.00 -1.00 -0.98 0.0693
0.00 -1.00 -1.98 0.0572
-1.00 -1.00 -0.98 0.0574
1.00 1.00 0.98 0.1000
-2.01 -2.00 -0.96 0.0555
-1.01 -2.00 -1.96 0.0588
-1.00 0.00 1.00 0.0707
-2.00 -1.00 0.02 0.0630
-1.00 0.00 2.00 0.0627
-1.00 -1.00 2.02 0.0674
1.00 0.00 -2.00 0.1043
1.00 1.00 -2.02 0.0922
-1.00 -2.00 2.04 0.0630
0.00 -1.00 0.02 0.0557
1.00 -2.00 -1.97 0.0579
0.00 -1.00 2.02 0.0592
1.00 -2.00 1.03 0.0474
0.00 1.00 -2.02 0.0795
0.00 0.00 1.00 0.0767
0.00 0.00 -1.00 0.0526
1.00 -1.00 -0.99 0.0675

_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.129
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11018
_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         26.371
_diffrn_reflns_theta_min         1.627
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1508
_reflns_number_total             1756
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0198P)²+0.9690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0578
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H14A(0.5) H14B(0.5) H14C(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.91214(2) 0.750000 0.67279(2) 0.02523(11) Uani 1 2 d S T P . .
HN3 H 0.663(4) 0.750000 0.6344(17) 0.033(13) Uiso 1 2 d S . P . .
S1 S 0.26470(9) 0.750000 0.43254(4) 0.0183(2) Uani 1 2 d S T P . .
N1 N 0.3787(3) 0.750000 0.48076(12) 0.0166(7) Uani 1 2 d S T P . .
C1 C 0.3112(3) 0.750000 0.52658(15) 0.0134(8) Uani 1 2 d S T P . .
N2 N 0.1736(3) 0.750000 0.52609(12) 0.0129(7) Uani 1 2 d S T P . .
C2 C 0.3810(3) 0.750000 0.57850(15) 0.0142(8) Uani 1 2 d S T P . .
N3 N 0.5795(3) 0.750000 0.63025(14) 0.0172(7) Uani 1 2 d S T P . .
C3 C 0.5220(4) 0.750000 0.58195(16) 0.0164(9) Uani 1 2 d S T P . .
H3 H 0.576194 0.750000 0.550571 0.020 Uiso 1 2 calc R U P . .
C4 C 0.5094(4) 0.750000 0.67583(16) 0.0193(9) Uani 1 2 d S T P . .
H4 H 0.555673 0.750000 0.709113 0.023 Uiso 1 2 calc R U P . .
N4 N -0.2435(3) 0.750000 0.49420(12) 0.0148(7) Uani 1 2 d S T P . .
C5 C 0.3705(4) 0.750000 0.67450(15) 0.0195(9) Uani 1 2 d S T P . .
H5 H 0.319733 0.750000 0.706753 0.023 Uiso 1 2 calc R U P . .
N5 N 0.5022(4) 0.250000 0.66769(15) 0.0334(10) Uani 1 2 d S T P . .
C6 C 0.3054(4) 0.750000 0.62581(15) 0.0171(9) Uani 1 2 d S T P . .
H6 H 0.209129 0.750000 0.624348 0.021 Uiso 1 2 calc R U P . .
C7 C 0.1312(3) 0.750000 0.47686(15) 0.0142(8) Uani 1 2 d S T P . .
C9 C -0.1091(3) 0.750000 0.50301(16) 0.0145(8) Uani 1 2 d S T P . .
H9 H -0.078065 0.750000 0.538928 0.017 Uiso 1 2 calc R U P . .
C8 C -0.0134(3) 0.750000 0.46247(15) 0.0130(8) Uani 1 2 d S T P . .
C10 C -0.2842(4) 0.750000 0.44316(15) 0.0167(9) Uani 1 2 d S T P . .
H10 H -0.378844 0.750000 0.436144 0.020 Uiso 1 2 calc R U P . .
C11 C -0.1958(4) 0.750000 0.39977(15) 0.0175(9) Uani 1 2 d S T P . .
H11 H -0.229524 0.750000 0.364217 0.021 Uiso 1 2 calc R U P . .
C12 C -0.0575(3) 0.750000 0.40972(15) 0.0158(8) Uani 1 2 d S T P . .
H12 H 0.005817 0.750000 0.381112 0.019 Uiso 1 2 calc R U P . .
C13 C 0.5700(4) 0.250000 0.70416(18) 0.0268(10) Uani 1 2 d S T P . .
C14 C 0.6575(6) 0.250000 0.7512(2) 0.0649(18) Uani 1 2 d S T P . .
H14A H 0.748160 0.299325 0.741208 0.097 Uiso 0.5 1 calc R U P . .
H14B H 0.663916 0.107529 0.765538 0.097 Uiso 0.5 1 calc R U P . .
H14C H 0.619304 0.343146 0.778423 0.097 Uiso 0.5 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.650(3) . ?
S1 C7 1.722(4) . ?
N1 C1 1.326(4) . ?
C1 N2 1.357(4) . ?
C1 C2 1.471(5) . ?
N2 C7 1.302(5) . ?
C2 C3 1.394(5) . ?
C2 C6 1.399(5) . ?
N3 HN3 0.83(4) . ?
N3 C3 1.335(5) . ?
N3 C4 1.334(5) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.370(5) . ?
N4 C9 1.343(4) . ?
N4 C10 1.339(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(5) . ?
N5 C13 1.131(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.471(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.386(5) . ?
C8 C12 1.390(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.460(6) . ?
C14 H14A 0.98(3) 7_565 ?
C14 H14A 0.9800 . ?
C14 H14B 0.980(13) 7_565 ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14C 0.98(4) 7_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C7 92.85(17) . . ?
C1 N1 S1 106.9(2) . . ?
N1 C1 N2 119.6(3) . . ?
N1 C1 C2 122.0(3) . . ?
N2 C1 C2 118.4(3) . . ?
C7 N2 C1 109.3(3) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 C6 118.6(3) . . ?
C6 C2 C1 119.9(3) . . ?
C3 N3 HN3 122(3) . . ?
C4 N3 HN3 114(3) . . ?
C4 N3 C3 123.7(3) . . ?
C2 C3 H3 120.7 . . ?
N3 C3 C2 118.7(4) . . ?
N3 C3 H3 120.7 . . ?
N3 C4 H4 120.1 . . ?
N3 C4 C5 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C10 N4 C9 116.9(3) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C2 C6 H6 120.0 . . ?
C5 C6 C2 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
N2 C7 S1 111.4(3) . . ?
N2 C7 C8 122.9(3) . . ?
C8 C7 S1 125.7(3) . . ?
N4 C9 H9 118.3 . . ?
N4 C9 C8 123.5(3) . . ?
C8 C9 H9 118.3 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 C12 118.9(3) . . ?
C12 C8 C7 122.4(3) . . ?
N4 C10 H10 118.1 . . ?
N4 C10 C11 123.8(3) . . ?
C11 C10 H10 118.1 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.4(4) . . ?
C12 C11 H11 120.8 . . ?
C8 C12 H12 120.7 . . ?
C11 C12 C8 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
N5 C13 C14 180.0(5) . . ?
C13 C14 H14A 109.5(6) . 7_565 ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5(3) . 7_565 ?
C13 C14 H14C 109.5 . . ?
C13 C14 H14C 109.5(9) . 7_565 ?
H14A C14 H14A 37.5 . 7_565 ?
H14A C14 H14B 109.5 7_565 7_565 ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14B 74.7 . 7_565 ?
H14A C14 H14C 136.3 . 7_565 ?
H14A C14 H14C 109.5 7_565 7_565 ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14A 74.7 . 7_565 ?
H14B C14 H14B 136.3 . 7_565 ?
H14B C14 H14C 37.5 . 7_565 ?
H14B C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 7_565 7_565 ?
H14C C14 H14A 136.3 . 7_565 ?
H14C C14 H14B 37.5 . 7_565 ?
H14C C14 H14C 74.7 . 7_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 HN3 I1 0.83(4) 2.64(4) 3.449(3) 166(4) . yes
C3 H3 N4 0.95 2.27 3.190(5) 162.7 1_655 yes
C4 H4 I1 0.95 3.28 3.909(4) 125.7 6_557 yes
C5 H5 I1 0.95 3.15 3.845(4) 131.4 6_557 yes
C10 H10 N1 0.95 2.64 3.455(5) 144.3 1_455 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 N2 0.000(1) . . . . ?
S1 N1 C1 C2 180.000(1) . . . . ?
S1 C7 C8 C9 180.000(1) . . . . ?
S1 C7 C8 C12 0.000(1) . . . . ?
N1 S1 C7 N2 0.000(1) . . . . ?
N1 S1 C7 C8 180.000(1) . . . . ?
N1 C1 N2 C7 0.000(1) . . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
N1 C1 C2 C6 180.000(1) . . . . ?
C1 N2 C7 S1 0.000(1) . . . . ?
C1 N2 C7 C8 180.000(1) . . . . ?
C1 C2 C3 N3 180.000(1) . . . . ?
C1 C2 C6 C5 180.000(1) . . . . ?
N2 C1 C2 C3 180.000(1) . . . . ?
N2 C1 C2 C6 0.000(1) . . . . ?
N2 C7 C8 C9 0.000(1) . . . . ?
N2 C7 C8 C12 180.000(1) . . . . ?
C2 C1 N2 C7 180.000(1) . . . . ?
N3 C4 C5 C6 0.000(2) . . . . ?
C3 C2 C6 C5 0.000(2) . . . . ?
C3 N3 C4 C5 0.000(2) . . . . ?
C4 N3 C3 C2 0.000(2) . . . . ?
C4 C5 C6 C2 0.000(2) . . . . ?
N4 C9 C8 C7 180.000(1) . . . . ?
N4 C9 C8 C12 0.000(1) . . . . ?
N4 C10 C11 C12 0.000(1) . . . . ?
C6 C2 C3 N3 0.000(1) . . . . ?
C7 S1 N1 C1 0.000(1) . . . . ?
C7 C8 C12 C11 180.000(1) . . . . ?
C9 N4 C10 C11 0.000(1) . . . . ?
C9 C8 C12 C11 0.000(1) . . . . ?
C10 N4 C9 C8 0.000(1) . . . . ?
C10 C11 C12 C8 0.000(1) . . . . ?

_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_mo_d8_5783_6mar22_ajp1_0m
_database_code_depnum_ccdc_archive 'CCDC 2182009'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi4 I16, 2(I2), 2(C12 H10 N4 S), 2(C2 H3 N)'
_chemical_formula_sum            'C28 H26 Bi4 I20 N10 S2'
_chemical_formula_weight         3940.63
_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'
S S 0.1246 0.1234 '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                   10.789(2)
_cell_length_b                   12.598(3)
_cell_length_c                   15.026(3)
_cell_angle_alpha                107.107(9)
_cell_angle_beta                 95.518(8)
_cell_angle_gamma                111.229(8)
_cell_volume                     1771.9(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9763
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.127
_shelx_estimated_absorpt_T_min   0.094
_exptl_absorpt_coefficient_mu    18.703
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.693
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.188
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            85055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_min         1.909
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8325
_reflns_number_total             8860
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         1.079
_refine_diff_density_min         -2.205
_refine_diff_density_rms         0.304
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         8860
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.243
_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)+7.3146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0613
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
S1A \\sim N3A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
2. Others
 Sof(N3B)=Sof(S1B)=1-FVAR(1)
 Sof(S1A)=Sof(N3A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(HN1), N4(HN4), C3(H3), C4(H1), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.34565(2) 0.98168(2) 0.61024(2) 0.00942(5) Uani 1 1 d . . . . .
Bi2 Bi 0.19466(2) 0.72617(2) 0.28065(2) 0.00848(5) Uani 1 1 d . . . . .
I1 I 0.25253(4) 1.15441(4) 0.71618(3) 0.02044(9) Uani 1 1 d . . . . .
I2 I 0.59080(4) 1.04621(3) 0.76851(3) 0.01426(8) Uani 1 1 d . . . . .
I3 I 0.16714(4) 0.77823(4) 0.65321(3) 0.02146(9) Uani 1 1 d . . . . .
I4 I 0.12371(4) 0.92286(3) 0.43226(3) 0.01025(7) Uani 1 1 d . . . . .
I5 I 0.44744(3) 0.79726(3) 0.45424(3) 0.01039(7) Uani 1 1 d . . . . .
I6 I 0.01883(4) 0.53867(3) 0.34101(3) 0.01381(8) Uani 1 1 d . . . . .
I7 I -0.02083(4) 0.72030(3) 0.13919(3) 0.01174(7) Uani 1 1 d . . . . .
I8 I 0.25952(4) 0.54664(3) 0.13735(3) 0.01917(9) Uani 1 1 d . . . . .
I9 I 0.13554(4) 0.25626(4) 0.14441(3) 0.01852(9) Uani 1 1 d . . . . .
I10 I 0.06274(4) 0.02748(4) 0.15022(3) 0.02074(9) Uani 1 1 d . . . . .
N1 N 0.6897(5) 0.1409(5) 0.0770(4) 0.0165(10) Uani 1 1 d . . . . .
HN1 H 0.666294 0.062405 0.063886 0.020 Uiso 1 1 calc R U . . .
N2 N 0.5104(5) 0.3232(4) 0.2699(4) 0.0145(10) Uani 1 1 d . . . . .
N4 N 0.2267(5) 0.2251(5) 0.4376(4) 0.0176(11) Uani 1 1 d . . . . .
HN4 H 0.197897 0.151596 0.440509 0.021 Uiso 1 1 calc R U . . .
C1 C 0.6000(6) 0.3804(5) 0.2254(4) 0.0139(11) Uani 1 1 d . . . . .
C2 C 0.6643(5) 0.3195(5) 0.1586(4) 0.0107(11) Uani 1 1 d . . . . .
C3 C 0.6303(6) 0.1963(5) 0.1379(4) 0.0146(11) Uani 1 1 d . . . . .
H3 H 0.565699 0.151790 0.166575 0.017 Uiso 1 1 calc R U . . .
C4 C 0.7833(6) 0.1989(6) 0.0350(4) 0.0176(12) Uani 1 1 d . . . . .
H1 H 0.824414 0.156243 -0.006575 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8184(6) 0.3208(6) 0.0532(5) 0.0195(13) Uani 1 1 d . . . . .
H5 H 0.882749 0.362902 0.023061 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7588(6) 0.3829(6) 0.1164(5) 0.0182(12) Uani 1 1 d . . . . .
H6 H 0.783159 0.467409 0.129994 0.022 Uiso 1 1 calc R U . . .
C7 C 0.4701(6) 0.4047(5) 0.3240(4) 0.0120(11) Uani 1 1 d . . . . .
C8 C 0.3702(6) 0.3705(5) 0.3815(4) 0.0117(11) Uani 1 1 d . . . . .
C9 C 0.3202(6) 0.2546(5) 0.3849(4) 0.0155(12) Uani 1 1 d . . . . .
H9 H 0.350963 0.196149 0.350796 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1755(6) 0.3014(6) 0.4855(5) 0.0194(13) Uani 1 1 d . . . . .
H10 H 0.108050 0.275721 0.519973 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2233(6) 0.4186(6) 0.4835(5) 0.0199(13) Uani 1 1 d . . . . .
H11 H 0.190615 0.475146 0.518188 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3185(6) 0.4523(6) 0.4309(5) 0.0190(13) Uani 1 1 d . . . . .
H12 H 0.349558 0.531850 0.428056 0.023 Uiso 1 1 calc R U . . .
S1A S 0.6369(5) 0.5296(4) 0.2598(4) 0.0171(10) Uani 0.622(11) 1 d . U P A 1
N3A N 0.528(2) 0.5212(16) 0.3312(13) 0.021(4) Uani 0.622(11) 1 d . U P A 1
N3B N 0.615(3) 0.494(3) 0.233(2) 0.028(8) Uani 0.378(11) 1 d . . P A 2
S1B S 0.5298(10) 0.5396(7) 0.3086(6) 0.0150(16) Uani 0.378(11) 1 d . . P A 2
N5 N 0.6306(6) -0.1079(5) 0.0295(4) 0.0242(12) Uani 1 1 d . . . . .
C13 C 0.6155(6) -0.2028(6) 0.0256(4) 0.0176(12) Uani 1 1 d . . . . .
C14 C 0.5921(7) -0.3269(5) 0.0208(5) 0.0203(13) Uani 1 1 d . . . . .
H14A H 0.560841 -0.381784 -0.046208 0.030 Uiso 1 1 calc R U . . .
H14B H 0.522400 -0.354472 0.055935 0.030 Uiso 1 1 calc R U . . .
H14C H 0.677382 -0.327376 0.049318 0.030 Uiso 1 1 calc R U . . .


_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 2.8517(6) . ?
Bi1 I2 3.0674(7) . ?
Bi1 I3 2.8869(7) . ?
Bi1 I4 3.1229(7) . ?
Bi1 I5 3.3435(7) 2_676 ?
Bi1 I5 3.3522(6) . ?
Bi2 I2 3.3008(7) 2_676 ?
Bi2 I4 3.2100(7) . ?
Bi2 I5 3.2453(7) . ?
Bi2 I6 2.8892(6) . ?
Bi2 I7 2.9600(6) . ?
Bi2 I8 2.9686(6) . ?
I9 I10 2.7302(8) . ?
N1 HN1 0.8800 . ?
N1 C3 1.341(8) . ?
N1 C4 1.347(9) . ?
N2 C1 1.343(8) . ?
N2 C7 1.343(7) . ?
N4 HN4 0.8800 . ?
N4 C9 1.355(8) . ?
N4 C10 1.343(8) . ?
C1 C2 1.464(8) . ?
C1 S1A 1.675(7) . ?
C1 N3B 1.35(3) . ?
C2 C3 1.386(8) . ?
C2 C6 1.383(8) . ?
C3 H3 0.9500 . ?
C4 H1 0.9500 . ?
C4 C5 1.375(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.467(8) . ?
C7 N3A 1.336(18) . ?
C7 S1B 1.681(10) . ?
C8 C9 1.381(8) . ?
C8 C12 1.404(8) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.387(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(9) . ?
C12 H12 0.9500 . ?
S1A N3A 1.66(2) . ?
N3B S1B 1.64(3) . ?
N5 C13 1.128(8) . ?
C13 C14 1.470(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Bi1 I2 96.361(19) . . ?
I1 Bi1 I3 96.17(2) . . ?
I1 Bi1 I4 87.937(18) . . ?
I1 Bi1 I5 169.770(13) . . ?
I1 Bi1 I5 87.53(2) . 2_676 ?
I2 Bi1 I4 172.448(13) . . ?
I2 Bi1 I5 86.871(18) . 2_676 ?
I2 Bi1 I5 90.702(19) . . ?
I3 Bi1 I2 94.571(18) . . ?
I3 Bi1 I4 91.124(18) . . ?
I3 Bi1 I5 90.61(2) . . ?
I3 Bi1 I5 175.839(13) . 2_676 ?
I4 Bi1 I5 84.273(18) . . ?
I4 Bi1 I5 87.115(18) . 2_676 ?
I5 Bi1 I5 85.465(19) 2_676 . ?
I4 Bi2 I2 87.70(2) . 2_676 ?
I4 Bi2 I5 84.670(18) . . ?
I5 Bi2 I2 84.753(17) . 2_676 ?
I6 Bi2 I2 175.005(12) . 2_676 ?
I6 Bi2 I4 89.28(2) . . ?
I6 Bi2 I5 91.005(19) . . ?
I6 Bi2 I7 96.879(19) . . ?
I6 Bi2 I8 91.60(2) . . ?
I7 Bi2 I2 86.846(18) . 2_676 ?
I7 Bi2 I4 85.339(19) . . ?
I7 Bi2 I5 167.184(12) . . ?
I7 Bi2 I8 93.71(2) . . ?
I8 Bi2 I2 91.48(2) . 2_676 ?
I8 Bi2 I4 178.774(13) . . ?
I8 Bi2 I5 96.167(19) . . ?
Bi1 I2 Bi2 96.228(17) . 2_676 ?
Bi1 I4 Bi2 97.903(18) . . ?
Bi1 I5 Bi1 94.536(19) 2_676 . ?
Bi2 I5 Bi1 92.085(17) . 2_676 ?
Bi2 I5 Bi1 92.751(19) . . ?
C3 N1 HN1 118.3 . . ?
C3 N1 C4 123.5(5) . . ?
C4 N1 HN1 118.3 . . ?
C1 N2 C7 107.6(5) . . ?
C9 N4 HN4 118.1 . . ?
C10 N4 HN4 118.1 . . ?
C10 N4 C9 123.9(5) . . ?
N2 C1 C2 123.2(5) . . ?
N2 C1 S1A 112.7(5) . . ?
N2 C1 N3B 117.2(16) . . ?
C2 C1 S1A 123.9(5) . . ?
N3B C1 C2 118.9(15) . . ?
C3 C2 C1 119.3(5) . . ?
C6 C2 C1 121.2(5) . . ?
C6 C2 C3 119.6(5) . . ?
N1 C3 C2 119.2(6) . . ?
N1 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
N1 C4 H1 120.6 . . ?
N1 C4 C5 118.8(6) . . ?
C5 C4 H1 120.6 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C2 C6 C5 119.1(6) . . ?
C2 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N2 C7 C8 121.3(5) . . ?
N2 C7 S1B 113.7(5) . . ?
C8 C7 S1B 124.6(5) . . ?
N3A C7 N2 119.8(10) . . ?
N3A C7 C8 118.8(10) . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 C12 118.2(6) . . ?
C12 C8 C7 121.3(5) . . ?
N4 C9 C8 119.2(5) . . ?
N4 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N4 C10 H10 120.8 . . ?
N4 C10 C11 118.4(6) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.5(6) . . ?
C12 C11 H11 120.2 . . ?
C8 C12 H12 119.6 . . ?
C11 C12 C8 120.7(6) . . ?
C11 C12 H12 119.6 . . ?
N3A S1A C1 92.9(7) . . ?
C7 N3A S1A 106.8(13) . . ?
C1 N3B S1B 110(2) . . ?
N3B S1B C7 91.2(13) . . ?
N5 C13 C14 178.5(7) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 C6 1.4(9) . . . . ?
N2 C1 C2 C3 1.3(9) . . . . ?
N2 C1 C2 C6 -178.3(6) . . . . ?
N2 C1 S1A N3A -2.7(8) . . . . ?
N2 C1 N3B S1B 7(2) . . . . ?
N2 C7 C8 C9 3.3(9) . . . . ?
N2 C7 C8 C12 -173.9(5) . . . . ?
N2 C7 N3A S1A 3.2(15) . . . . ?
N2 C7 S1B N3B -2.2(11) . . . . ?
N4 C10 C11 C12 1.7(9) . . . . ?
C1 N2 C7 C8 179.3(5) . . . . ?
C1 N2 C7 N3A -5.2(12) . . . . ?
C1 N2 C7 S1B 6.2(7) . . . . ?
C1 C2 C3 N1 -179.7(5) . . . . ?
C1 C2 C6 C5 179.6(6) . . . . ?
C1 S1A N3A C7 -0.2(11) . . . . ?
C1 N3B S1B C7 -2.6(17) . . . . ?
C2 C1 S1A N3A -179.2(8) . . . . ?
C2 C1 N3B S1B 177.9(10) . . . . ?
C3 N1 C4 C5 -1.5(9) . . . . ?
C3 C2 C6 C5 0.1(9) . . . . ?
C4 N1 C3 C2 0.9(9) . . . . ?
C4 C5 C6 C2 -0.7(9) . . . . ?
C6 C2 C3 N1 -0.2(8) . . . . ?
C7 N2 C1 C2 -178.9(5) . . . . ?
C7 N2 C1 S1A 4.7(6) . . . . ?
C7 N2 C1 N3B -8.5(15) . . . . ?
C7 C8 C9 N4 -179.2(5) . . . . ?
C7 C8 C12 C11 179.1(6) . . . . ?
C8 C7 N3A S1A 178.8(6) . . . . ?
C8 C7 S1B N3B -175.1(11) . . . . ?
C9 N4 C10 C11 -1.8(9) . . . . ?
C9 C8 C12 C11 1.8(9) . . . . ?
C10 N4 C9 C8 1.9(9) . . . . ?
C10 C11 C12 C8 -1.7(10) . . . . ?
C12 C8 C9 N4 -1.8(8) . . . . ?
S1A C1 C2 C3 177.3(5) . . . . ?
S1A C1 C2 C6 -2.2(8) . . . . ?
N3A C7 C8 C9 -172.2(10) . . . . ?
N3A C7 C8 C12 10.5(12) . . . . ?
N3B C1 C2 C3 -168.9(15) . . . . ?
N3B C1 C2 C6 11.6(16) . . . . ?
S1B C7 C8 C9 175.7(6) . . . . ?
S1B C7 C8 C12 -1.6(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT434_mo_d8_5783_6mar22_ajp1_0m 
;
PROBLEM: Short Inter HL..HL Contact I8       ..I9       .       3.45 Ang.  
RESPONSE: This contact represents an I...I halogen bond
;
####################################################################### 
# 
# 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_mo_d8_5846_27mar22_ajp1_0m
_database_code_depnum_ccdc_archive 'CCDC 2182008'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 I9, C12 H10 N4 S, 3(H2 O), C12 H9 N4 S'
_chemical_formula_sum            'C24 H25 Bi2 I9 N8 O3 S2'
_chemical_formula_weight         2097.70
_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'
S S 0.1246 0.1234 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3663(5)
_cell_length_b                   24.1622(12)
_cell_length_c                   12.9374(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.602(2)
_cell_angle_gamma                90
_cell_volume                     2506.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9605
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.256
_shelx_estimated_absorpt_T_min   0.149
_exptl_absorpt_coefficient_mu    12.671
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.780
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.148
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0509
_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       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            77273
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.635
_diffrn_reflns_theta_min         1.846
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                13212
_reflns_number_total             13925
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         3.772
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.215
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.010(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         13925
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0094P)²+10.7712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0718
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.99005
 0.00995
2. Restrained distances
 N4-H4
 0.86 with sigma of 0.02
 H7-N7
 0.86 with sigma of 0.02
 H1O3-O3 = H2O3-O3
 0.87 with sigma of 0.02
 H2O3-H1O3
 1.38 with sigma of 0.04
 C1-N2A \\sim C7-N2B
 with sigma of 0.02
 C7-S1A \\sim C1-S1B
 with sigma of 0.02
 C17-H7 \\sim C16-H7
 with sigma of 0.02
 H1O3-O3 \\sim H2O3-O3
 with sigma of 0.001
3. Restrained planarity
 N7, H7, C16, C17
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
S1B \\sim N2B: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
S1A \\sim N2A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
S2 \\sim N6: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
5. Others
 Sof(S1B)=Sof(N2B)=1-FVAR(1)
 Sof(S1A)=Sof(N2A)=FVAR(1)
 Fixed X: H1A(0.25933) H1B(0.191991) H2C(1.31604) H2D(1.313) H1O3(0.828701)
 H2O3(0.788)
 Fixed Y: H1A(0.21096) H1B(0.24797) H2C(0.73082) H2D(0.780509) H1O3(0.30181)
 H2O3(0.35797)
 Fixed Z: H1A(-0.246739) H1B(-0.18998) H2C(1.132721) H2D(1.080189)
 H1O3(0.73037) H2O3(0.706539)
6.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
 C24(H24), C3(H3), C4(H4A), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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 0.17063(5) 0.47832(2) 0.05692(3) 0.01573(8) Uani 1 1 d . . . . .
Bi2 Bi 0.17561(5) 0.33537(2) 0.24568(3) 0.01673(8) Uani 1 1 d . . . . .
I1 I 0.46877(9) 0.54200(3) 0.05423(6) 0.02499(15) Uani 1 1 d . . . . .
I2 I -0.02870(9) 0.57773(3) 0.06196(6) 0.02285(15) Uani 1 1 d . . . . .
I3 I 0.05393(10) 0.46288(3) -0.18188(6) 0.02744(16) Uani 1 1 d . . . . .
I4 I 0.40825(9) 0.36725(3) 0.09852(6) 0.02025(14) Uani 1 1 d . . . . .
I5 I 0.25866(8) 0.46611(3) 0.31319(5) 0.01695(13) Uani 1 1 d . . . . .
I6 I -0.11825(9) 0.38931(3) 0.06645(6) 0.02314(15) Uani 1 1 d . . . . .
I7 I 0.14005(10) 0.22759(3) 0.14094(6) 0.02695(16) Uani 1 1 d . . . . .
I8 I -0.04720(9) 0.31148(3) 0.38158(6) 0.02402(15) Uani 1 1 d . . . . .
I9 I 0.47836(8) 0.30674(3) 0.42831(6) 0.02065(14) Uani 1 1 d . . . . .
S2 S 1.1066(6) 0.60103(17) 0.3948(4) 0.0457(9) Uani 1 1 d . U . . .
N5 N 1.0666(11) 0.5734(4) 0.5744(8) 0.0224(19) Uani 1 1 d . . . . .
N6 N 1.1961(16) 0.6428(5) 0.4933(10) 0.0356(15) Uani 1 1 d . U . . .
N7 N 1.3207(15) 0.6985(5) 0.8870(11) 0.040(3) Uani 1 1 d D . . . .
H7 H 1.347(8) 0.716(2) 0.947(3) 0.03(4) Uiso 1 1 d D . . . .
N8 N 0.6905(13) 0.4300(4) 0.3570(9) 0.029(2) Uani 1 1 d . . . . .
H8 H 0.619353 0.402879 0.332881 0.034 Uiso 1 1 calc R U . . .
C13 C 1.1696(14) 0.6187(5) 0.5879(11) 0.027(3) Uani 1 1 d . . . . .
C14 C 1.2313(14) 0.6440(5) 0.6944(11) 0.025(2) Uani 1 1 d . . . . .
C15 C 1.3323(15) 0.6908(5) 0.7081(13) 0.034(3) Uani 1 1 d . . . . .
H15 H 1.373520 0.703846 0.651261 0.041 Uiso 1 1 calc R U . . .
C16 C 1.3708(17) 0.7176(5) 0.8052(13) 0.042(4) Uani 1 1 d D . . . .
H16 H 1.434758 0.750659 0.814321 0.051 Uiso 1 1 calc R U . . .
C17 C 1.2268(16) 0.6529(5) 0.8764(11) 0.029(3) Uani 1 1 d D . . . .
H17 H 1.190235 0.640326 0.935456 0.035 Uiso 1 1 calc R U . . .
C18 C 1.1830(15) 0.6244(5) 0.7817(11) 0.027(3) Uani 1 1 d . . . . .
H18 H 1.119810 0.591217 0.775426 0.033 Uiso 1 1 calc R U . . .
C19 C 1.0194(15) 0.5605(5) 0.4686(10) 0.024(2) Uani 1 1 d . . . . .
C20 C 0.9061(14) 0.5142(5) 0.4286(10) 0.025(2) Uani 1 1 d . . . . .
C21 C 0.8559(14) 0.4815(6) 0.5024(10) 0.028(2) Uani 1 1 d . . . . .
H21 H 0.896677 0.488475 0.577594 0.033 Uiso 1 1 calc R U . . .
C22 C 0.7440(16) 0.4380(5) 0.4632(11) 0.032(3) Uani 1 1 d . . . . .
H22 H 0.707252 0.414856 0.511200 0.038 Uiso 1 1 calc R U . . .
C23 C 0.7384(16) 0.4607(6) 0.2843(11) 0.031(3) Uani 1 1 d . . . . .
H23 H 0.697873 0.452395 0.209600 0.037 Uiso 1 1 calc R U . . .
C24 C 0.8440(14) 0.5032(5) 0.3183(10) 0.026(2) Uani 1 1 d . . . . .
H24 H 0.876368 0.525631 0.267511 0.032 Uiso 1 1 calc R U . . .
O1 O 0.2474(18) 0.2464(4) -0.2372(10) 0.057(4) Uani 1 1 d . . . . .
H1A H 0.259330 0.210960 -0.246739 0.086 Uiso 1 1 d . U . . .
H1B H 0.191991 0.247970 -0.189980 0.086 Uiso 1 1 d . U . . .
O2 O 1.348(2) 0.7477(5) 1.0849(12) 0.099(7) Uani 1 1 d . . . . .
H2C H 1.316040 0.730820 1.132721 0.149 Uiso 1 1 d . U . . .
H2D H 1.313000 0.780509 1.080189 0.149 Uiso 1 1 d . U . . .
O3 O 0.869(3) 0.3333(2) 0.7129(14) 0.129(8) Uani 1 1 d D . . . .
H1O3 H 0.828701 0.301810 0.730370 0.193 Uiso 1 1 d D U . . .
H2O3 H 0.788000 0.357970 0.706539 0.193 Uiso 1 1 d D U . . .
N1 N 0.5330(12) 0.5267(4) -0.3886(8) 0.023(2) Uani 1 1 d . . . . .
N3 N 0.6941(14) 0.6704(4) -0.6292(9) 0.030(2) Uani 1 1 d . . . . .
N4 N 0.3470(13) 0.3469(4) -0.2650(8) 0.024(2) Uani 1 1 d D . . . .
H4 H 0.303(13) 0.314(2) -0.269(9) 0.01(3) Uiso 1 1 d D . . . .
C1 C 0.6161(13) 0.5762(5) -0.3712(9) 0.021(2) Uani 1 1 d D . . . .
C2 C 0.6393(13) 0.6090(4) -0.4596(10) 0.020(2) Uani 1 1 d . . . . .
C3 C 0.5698(14) 0.5920(5) -0.5661(9) 0.023(2) Uani 1 1 d . . . . .
H3 H 0.502276 0.559774 -0.582039 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6011(17) 0.6228(5) -0.6473(10) 0.030(3) Uani 1 1 d . . . . .
H4A H 0.555955 0.610597 -0.719597 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7590(16) 0.6853(5) -0.5285(11) 0.031(3) Uani 1 1 d . . . . .
H5 H 0.827395 0.717404 -0.514646 0.037 Uiso 1 1 calc R U . . .
C6 C 0.7340(15) 0.6569(5) -0.4397(10) 0.026(2) Uani 1 1 d . . . . .
H6 H 0.780705 0.670058 -0.368263 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5382(13) 0.5048(5) -0.2915(9) 0.022(2) Uani 1 1 d D . . . .
C8 C 0.4662(13) 0.4502(5) -0.2824(9) 0.021(2) Uani 1 1 d . . . . .
C9 C 0.3559(14) 0.4246(5) -0.3730(9) 0.023(2) Uani 1 1 d . . . . .
H9 H 0.322981 0.442914 -0.440817 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2974(15) 0.3728(5) -0.3611(10) 0.026(2) Uani 1 1 d . . . . .
H10 H 0.221607 0.355019 -0.420837 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4528(16) 0.3702(5) -0.1774(9) 0.028(3) Uani 1 1 d . . . . .
H11 H 0.486462 0.350187 -0.111445 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5117(17) 0.4221(5) -0.1830(11) 0.031(3) Uani 1 1 d . . . . .
H12 H 0.582685 0.439241 -0.120598 0.037 Uiso 1 1 calc R U . . .
S1A S 0.6304(10) 0.5490(3) -0.1909(6) 0.033(2) Uani 0.555(18) 1 d D U P A 1
N2A N 0.670(4) 0.5965(13) -0.273(2) 0.036(5) Uani 0.555(18) 1 d D U P A 1
S1B S 0.6984(12) 0.5869(3) -0.2340(7) 0.025(2) Uani 0.445(18) 1 d D U P A 2
N2B N 0.623(4) 0.5291(12) -0.198(2) 0.025(4) Uani 0.445(18) 1 d D U P A 2


_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 2.9393(8) . ?
Bi1 I2 2.9354(8) . ?
Bi1 I3 2.9856(9) . ?
Bi1 I4 3.2914(8) . ?
Bi1 I5 3.1980(8) . ?
Bi1 I6 3.2638(8) . ?
Bi2 I4 3.1817(8) . ?
Bi2 I5 3.2982(8) . ?
Bi2 I6 3.1404(8) . ?
Bi2 I7 2.9113(8) . ?
Bi2 I8 2.9618(8) . ?
Bi2 I9 3.0095(8) . ?
S2 N6 1.630(12) . ?
S2 C19 1.673(12) . ?
N5 C13 1.373(14) . ?
N5 C19 1.348(16) . ?
N6 C13 1.427(17) . ?
N7 H7 0.85(3) . ?
N7 C16 1.33(2) . ?
N7 C17 1.336(16) . ?
N8 H8 0.8800 . ?
N8 C22 1.332(17) . ?
N8 C23 1.346(18) . ?
C13 C14 1.460(19) . ?
C14 C15 1.393(15) . ?
C14 C18 1.387(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.37(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.362(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.462(16) . ?
C20 C21 1.393(18) . ?
C20 C24 1.398(17) . ?
C21 H21 0.9500 . ?
C21 C22 1.402(17) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.344(19) . ?
C24 H24 0.9500 . ?
O1 H1A 0.874(9) . ?
O1 H1B 0.867(10) . ?
O2 H2C 0.844(19) . ?
O2 H2D 0.840(15) . ?
O3 H1O3 0.888(12) . ?
O3 H2O3 0.888(12) . ?
N1 C1 1.368(14) . ?
N1 C7 1.353(15) . ?
N3 C4 1.370(16) . ?
N3 C5 1.311(18) . ?
N4 H4 0.87(3) . ?
N4 C10 1.348(16) . ?
N4 C11 1.346(16) . ?
C1 C2 1.450(16) . ?
C1 N2A 1.31(3) . ?
C1 S1B 1.730(13) . ?
C2 C3 1.396(16) . ?
C2 C6 1.383(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(18) . ?
C4 H4A 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.404(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.468(16) . ?
C7 S1A 1.691(12) . ?
C7 N2B 1.35(3) . ?
C8 C9 1.411(15) . ?
C8 C12 1.407(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.369(16) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.357(18) . ?
C12 H12 0.9500 . ?
S1A N2A 1.66(3) . ?
S1B N2B 1.65(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 I3 94.64(2) . . ?
I1 Bi1 I4 87.35(2) . . ?
I1 Bi1 I5 96.65(2) . . ?
I1 Bi1 I6 170.21(2) . . ?
I2 Bi1 I1 93.52(2) . . ?
I2 Bi1 I3 96.05(2) . . ?
I2 Bi1 I4 169.74(2) . . ?
I2 Bi1 I5 90.94(2) . . ?
I2 Bi1 I6 96.13(2) . . ?
I3 Bi1 I4 94.07(2) . . ?
I3 Bi1 I5 166.33(2) . . ?
I3 Bi1 I6 85.98(2) . . ?
I5 Bi1 I4 78.802(19) . . ?
I5 Bi1 I6 81.59(2) . . ?
I6 Bi1 I4 82.86(2) . . ?
I4 Bi2 I5 78.931(19) . . ?
I6 Bi2 I4 86.64(2) . . ?
I6 Bi2 I5 81.91(2) . . ?
I7 Bi2 I4 86.37(2) . . ?
I7 Bi2 I5 164.97(2) . . ?
I7 Bi2 I6 94.20(2) . . ?
I7 Bi2 I8 95.97(3) . . ?
I7 Bi2 I9 96.37(2) . . ?
I8 Bi2 I4 177.13(2) . . ?
I8 Bi2 I5 98.64(2) . . ?
I8 Bi2 I6 91.52(2) . . ?
I8 Bi2 I9 91.17(2) . . ?
I9 Bi2 I4 90.22(2) . . ?
I9 Bi2 I5 86.90(2) . . ?
I9 Bi2 I6 168.76(2) . . ?
Bi2 I4 Bi1 81.438(18) . . ?
Bi1 I5 Bi2 81.090(18) . . ?
Bi2 I6 Bi1 82.496(19) . . ?
N6 S2 C19 95.4(6) . . ?
C19 N5 C13 107.7(10) . . ?
C13 N6 S2 105.6(8) . . ?
C16 N7 H7 120(2) . . ?
C16 N7 C17 121.1(13) . . ?
C17 N7 H7 119(2) . . ?
C22 N8 H8 117.9 . . ?
C22 N8 C23 124.1(11) . . ?
C23 N8 H8 117.9 . . ?
N5 C13 N6 117.5(11) . . ?
N5 C13 C14 119.5(12) . . ?
N6 C13 C14 122.6(10) . . ?
C15 C14 C13 119.8(12) . . ?
C18 C14 C13 121.3(11) . . ?
C18 C14 C15 118.8(13) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.4(14) . . ?
C16 C15 H15 120.8 . . ?
N7 C16 C15 121.5(12) . . ?
N7 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
N7 C17 H17 119.7 . . ?
N7 C17 C18 120.5(13) . . ?
C18 C17 H17 119.7 . . ?
C14 C18 H18 120.2 . . ?
C17 C18 C14 119.6(11) . . ?
C17 C18 H18 120.2 . . ?
N5 C19 S2 113.2(9) . . ?
N5 C19 C20 120.6(10) . . ?
C20 C19 S2 126.2(10) . . ?
C21 C20 C19 119.0(11) . . ?
C21 C20 C24 119.6(11) . . ?
C24 C20 C19 121.4(12) . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.6(11) . . ?
C22 C21 H21 120.7 . . ?
N8 C22 C21 118.4(12) . . ?
N8 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
N8 C23 H23 120.3 . . ?
C24 C23 N8 119.4(12) . . ?
C24 C23 H23 120.3 . . ?
C20 C24 H24 120.1 . . ?
C23 C24 C20 119.9(12) . . ?
C23 C24 H24 120.1 . . ?
H1A O1 H1B 104.4(10) . . ?
H2C O2 H2D 110(2) . . ?
H1O3 O3 H2O3 105(2) . . ?
C7 N1 C1 108.0(10) . . ?
C5 N3 C4 117.0(11) . . ?
C10 N4 H4 111(8) . . ?
C11 N4 H4 127(8) . . ?
C11 N4 C10 122.5(10) . . ?
N1 C1 C2 121.6(10) . . ?
N1 C1 S1B 109.5(9) . . ?
C2 C1 S1B 128.6(9) . . ?
N2A C1 N1 120.2(16) . . ?
N2A C1 C2 118.1(16) . . ?
C3 C2 C1 120.4(10) . . ?
C6 C2 C1 120.6(10) . . ?
C6 C2 C3 119.0(11) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.7(11) . . ?
C4 C3 H3 120.7 . . ?
N3 C4 C3 123.2(11) . . ?
N3 C4 H4A 118.4 . . ?
C3 C4 H4A 118.4 . . ?
N3 C5 H5 117.9 . . ?
N3 C5 C6 124.2(12) . . ?
C6 C5 H5 117.9 . . ?
C2 C6 C5 117.9(11) . . ?
C2 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N1 C7 C8 121.4(10) . . ?
N1 C7 S1A 110.7(9) . . ?
C8 C7 S1A 127.9(10) . . ?
N2B C7 N1 122.0(17) . . ?
N2B C7 C8 116.3(17) . . ?
C9 C8 C7 120.9(11) . . ?
C12 C8 C7 119.8(10) . . ?
C12 C8 C9 119.3(11) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.5(11) . . ?
C10 C9 H9 120.7 . . ?
N4 C10 C9 120.2(11) . . ?
N4 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N4 C11 H11 119.9 . . ?
N4 C11 C12 120.2(11) . . ?
C12 C11 H11 119.9 . . ?
C8 C12 H12 120.4 . . ?
C11 C12 C8 119.2(12) . . ?
C11 C12 H12 120.4 . . ?
N2A S1A C7 94.3(11) . . ?
C1 N2A S1A 106.5(18) . . ?
N2B S1B C1 95.0(12) . . ?
C7 N2B S1B 105(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 N6 C13 N5 -7.1(13) . . . . ?
S2 N6 C13 C14 -179.9(9) . . . . ?
S2 C19 C20 C21 174.4(10) . . . . ?
S2 C19 C20 C24 -7.4(18) . . . . ?
N5 C13 C14 C15 -178.3(11) . . . . ?
N5 C13 C14 C18 -2.3(17) . . . . ?
N5 C19 C20 C21 -4.0(18) . . . . ?
N5 C19 C20 C24 174.3(11) . . . . ?
N6 S2 C19 N5 -5.9(11) . . . . ?
N6 S2 C19 C20 175.6(11) . . . . ?
N6 C13 C14 C15 -5.7(17) . . . . ?
N6 C13 C14 C18 170.3(11) . . . . ?
N7 C17 C18 C14 -2.4(19) . . . . ?
N8 C23 C24 C20 1.5(18) . . . . ?
C13 N5 C19 S2 2.4(12) . . . . ?
C13 N5 C19 C20 -179.0(10) . . . . ?
C13 C14 C15 C16 171.9(12) . . . . ?
C13 C14 C18 C17 -172.2(11) . . . . ?
C14 C15 C16 N7 3(2) . . . . ?
C15 C14 C18 C17 3.9(18) . . . . ?
C16 N7 C17 C18 1(2) . . . . ?
C17 N7 C16 C15 -2(2) . . . . ?
C18 C14 C15 C16 -4.2(18) . . . . ?
C19 S2 N6 C13 6.9(10) . . . . ?
C19 N5 C13 N6 3.1(14) . . . . ?
C19 N5 C13 C14 176.1(10) . . . . ?
C19 C20 C21 C22 178.5(11) . . . . ?
C19 C20 C24 C23 -179.2(11) . . . . ?
C20 C21 C22 N8 0.0(19) . . . . ?
C21 C20 C24 C23 -0.9(18) . . . . ?
C22 N8 C23 C24 -1.5(19) . . . . ?
C23 N8 C22 C21 1(2) . . . . ?
C24 C20 C21 C22 0.1(18) . . . . ?
N1 C1 C2 C3 3.1(16) . . . . ?
N1 C1 C2 C6 -175.2(11) . . . . ?
N1 C1 N2A S1A 5(3) . . . . ?
N1 C1 S1B N2B -1.4(15) . . . . ?
N1 C7 C8 C9 -15.1(16) . . . . ?
N1 C7 C8 C12 162.8(11) . . . . ?
N1 C7 S1A N2A -1.6(14) . . . . ?
N1 C7 N2B S1B 3(3) . . . . ?
N3 C5 C6 C2 2(2) . . . . ?
N4 C11 C12 C8 -2.6(19) . . . . ?
C1 N1 C7 C8 -177.2(10) . . . . ?
C1 N1 C7 S1A 4.3(12) . . . . ?
C1 N1 C7 N2B -4(2) . . . . ?
C1 C2 C3 C4 -177.0(11) . . . . ?
C1 C2 C6 C5 176.8(11) . . . . ?
C1 S1B N2B C7 0(2) . . . . ?
C2 C1 N2A S1A -178.3(11) . . . . ?
C2 C1 S1B N2B -175.3(16) . . . . ?
C2 C3 C4 N3 -2(2) . . . . ?
C3 C2 C6 C5 -1.6(17) . . . . ?
C4 N3 C5 C6 -2(2) . . . . ?
C5 N3 C4 C3 2(2) . . . . ?
C6 C2 C3 C4 1.4(17) . . . . ?
C7 N1 C1 C2 177.2(10) . . . . ?
C7 N1 C1 N2A -6(2) . . . . ?
C7 N1 C1 S1B 2.8(12) . . . . ?
C7 C8 C9 C10 177.5(11) . . . . ?
C7 C8 C12 C11 -175.7(11) . . . . ?
C7 S1A N2A C1 -2(2) . . . . ?
C8 C7 S1A N2A -180.0(15) . . . . ?
C8 C7 N2B S1B 176.4(12) . . . . ?
C8 C9 C10 N4 -1.0(17) . . . . ?
C9 C8 C12 C11 2.2(18) . . . . ?
C10 N4 C11 C12 1.3(19) . . . . ?
C11 N4 C10 C9 0.6(18) . . . . ?
C12 C8 C9 C10 -0.4(17) . . . . ?
S1A C7 C8 C9 163.1(10) . . . . ?
S1A C7 C8 C12 -19.0(16) . . . . ?
N2A C1 C2 C3 -173.4(19) . . . . ?
N2A C1 C2 C6 8(2) . . . . ?
S1B C1 C2 C3 176.3(10) . . . . ?
S1B C1 C2 C6 -2.1(17) . . . . ?
N2B C7 C8 C9 171.0(19) . . . . ?
N2B C7 C8 C12 -11(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.99005
2 0.00995

# start Validation Reply Form
_vrf_PLAT420_mo_d8_5846_27mar22_ajp1_0m 
;
PROBLEM: D-H Bond Without Acceptor  O3       --H1O3     .     Please Check 
RESPONSE: The water molecules in this structure act as either N-H...O acceptors,
C-H...O acceptors, or to fill void space without  significant standard H-bonding 
interactions.
;
####################################################################### 
# 
# 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_27jul20_ajp3_xprep_a
_database_code_depnum_ccdc_archive 'CCDC 2182006'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '10.667(I3), 2(C30 H23 Fe N10 O), 4(H2 O)'
_chemical_formula_sum            'C60 H54 Fe2 I32 N20 O6'
_chemical_formula_weight         5323.73
_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'
Fe Fe 0.3463 0.8444 '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      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                   10.36580(10)
_cell_length_b                   13.9906(2)
_cell_length_c                   21.5956(3)
_cell_angle_alpha                97.0570(10)
_cell_angle_beta                 94.9320(10)
_cell_angle_gamma                110.7400(10)
_cell_volume                     2878.31(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    72888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.370
_cell_measurement_theta_min      1.578
_shelx_estimated_absorpt_T_max   0.473
_shelx_estimated_absorpt_T_min   0.227
_exptl_absorpt_coefficient_mu    8.882
_exptl_absorpt_correction_T_max  0.528
_exptl_absorpt_correction_T_min  0.291
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.071
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2350
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.01 1.98 -5.01 0.0668
0.98 0.04 5.01 0.0328
-1.99 1.96 -5.03 0.1173
0.03 -2.03 -4.99 0.0885
-3.94 -5.08 -4.01 0.1218
0.01 -1.01 -1.00 0.0964
0.02 -5.01 1.02 0.1007
-1.00 -1.99 5.00 0.0587
1.00 -3.97 5.03 0.0859
-0.98 -0.04 -5.01 0.1103
-0.02 1.03 5.00 0.0314
-0.03 2.03 4.99 0.0379
-1.03 5.01 2.97 0.0770
0.96 5.03 1.99 0.0495
0.99 1.02 0.00 0.0663
1.99 4.01 -5.00 0.0553
-0.01 4.99 -4.02 0.0649
-0.01 -0.98 5.01 0.0374
-2.02 4.98 -1.04 0.1077
1.01 0.99 -5.00 0.0654
-1.01 -0.99 5.00 0.0689
-3.98 -4.04 4.98 0.1229
0.00 0.00 -1.00 0.0741
0.01 1.98 -5.01 0.0668
0.98 0.04 5.01 0.0328
-1.99 1.96 -5.03 0.1173
0.03 -2.03 -4.99 0.0885
-3.94 -5.08 -4.01 0.1218
0.01 -1.01 -1.00 0.0964
0.02 -5.01 1.02 0.1007
-1.00 -1.99 5.00 0.0587
1.00 -3.97 5.03 0.0859
-0.98 -0.04 -5.01 0.1103
-0.02 1.03 5.00 0.0314
-0.03 2.03 4.99 0.0379
-1.03 5.01 2.97 0.0770
0.96 5.03 1.99 0.0495
0.99 1.02 0.00 0.0663
1.99 4.01 -5.00 0.0553
-0.01 4.99 -4.02 0.0649
-0.01 -0.98 5.01 0.0374
-2.02 4.98 -1.04 0.1077
1.01 0.99 -5.00 0.0654
-1.01 -0.99 5.00 0.0689
-3.98 -4.04 4.98 0.1229
0.00 0.00 -1.00 0.0741

_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.099
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            72888
_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         26.370
_diffrn_reflns_theta_min         1.578
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9201
_reflns_number_total             11738
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         4.467
_refine_diff_density_min         -2.047
_refine_diff_density_rms         0.247
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         11738
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.090
_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)+(0.0608P)²+23.6516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N10-HN10
 0.86 with sigma of 0.02
 H1O1-O1 = H2O1-O1
 0.87 with sigma of 0.02
 H1O2-O2 = H2O2-O2
 0.87 with sigma of 0.01
 H1O1-H2O1
 1.38 with sigma of 0.04
 H1O2-H2O2
 1.38 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
C7 \\sim C8: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
within 2A
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C21(H26), C22(H27), C23(H28), C24(H29),
  C27(H20), C28(H21), C29(H22), C30(H23)
3.b X=CH2 refined with riding coordinates:
 N4(HN4A,HN4B)
;
_atom_sites_solution_hydrogens   mixed
_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
I3 I 0.71125(7) 0.61404(5) 0.31820(3) 0.03854(17) Uani 1 1 d . . . . .
I4 I 0.43086(7) 0.47513(5) 0.27667(3) 0.03349(16) Uani 1 1 d . . . . .
I5 I 0.13211(7) 0.34290(5) 0.21916(3) 0.04182(18) Uani 1 1 d . . . . .
I6 I 0.19315(7) 0.45308(5) 0.09856(3) 0.03499(16) Uani 1 1 d . . . . .
I7 I 0.23900(8) 0.56279(6) -0.00009(3) 0.0517(2) Uani 1 1 d . . . . .
I8 I -0.36764(8) 0.35044(5) 0.16270(4) 0.04677(19) Uani 1 1 d . . . . .
I9 I -0.22877(7) 0.22967(6) 0.09533(3) 0.04325(19) Uani 1 1 d . . . . .
I10 I -0.08997(8) 0.12184(7) 0.01877(3) 0.0490(2) Uani 1 1 d . . . . .
I11 I -0.06186(7) -0.02154(6) 0.12516(3) 0.04498(19) Uani 1 1 d . . . . .
I12 I -0.04685(8) -0.13522(6) 0.21859(4) 0.04733(19) Uani 1 1 d . . . . .
I13 I -0.32429(8) 0.18978(6) 0.40426(4) 0.04625(19) Uani 1 1 d . . . . .
I14 I -0.32738(7) 0.27632(5) 0.29725(4) 0.04224(18) Uani 1 1 d . . . . .
I15 I 0.14028(9) 0.30840(6) 0.38725(4) 0.0523(2) Uani 1 1 d . . . . .
I16 I 0.06030(7) 0.24576(5) 0.50228(3) 0.03962(17) Uani 1 1 d . . . . .
I17 I -0.05286(6) 0.17926(5) 0.62208(3) 0.03678(16) Uani 1 1 d . . . . .
I18 I -0.36506(8) 0.05021(6) 0.53255(3) 0.04552(19) Uani 1 1 d . . . . .
Fe1 Fe 0.44258(13) 0.86214(10) 0.21066(6) 0.0251(3) Uani 1 1 d . . . . .
O4 O 0.5284(8) 0.9302(6) 0.0388(3) 0.0453(18) Uani 1 1 d . . . . .
N1 N 0.5193(8) 0.7752(6) 0.1590(4) 0.0315(18) Uani 1 1 d . . . . .
N2 N 0.4575(8) 0.9322(6) 0.1378(4) 0.0335(19) Uani 1 1 d . . . . .
N3 N 0.3727(7) 0.9728(6) 0.2391(4) 0.0270(17) Uani 1 1 d . . . . .
N4 N 0.4006(8) 1.0568(6) 0.0904(4) 0.0354(19) Uani 1 1 d . . . . .
HN4A H 0.432459 1.041141 0.055624 0.043 Uiso 1 1 calc R U . . .
HN4B H 0.365337 1.105601 0.093371 0.043 Uiso 1 1 calc R U . . .
N5 N 0.2507(7) 0.7580(6) 0.1848(3) 0.0254(16) Uani 1 1 d . . . . .
N6 N 0.4221(7) 0.7958(5) 0.2795(3) 0.0229(15) Uani 1 1 d . . . . .
N7 N 0.6285(7) 0.9430(6) 0.2610(3) 0.0258(16) Uani 1 1 d . . . . .
N8 N 0.2844(7) 0.6734(6) 0.3354(3) 0.0246(16) Uani 1 1 d . . . . .
N9 N 0.5217(8) 0.7791(6) 0.3792(3) 0.0250(16) Uani 1 1 d . . . . .
N10 N 0.2520(9) 0.5948(6) 0.4440(4) 0.0348(19) Uani 1 1 d D . . . .
HN10 H 0.186(10) 0.573(11) 0.413(4) 0.08(5) Uiso 1 1 d D . . . .
C1 C 0.5471(9) 0.8067(8) 0.1016(5) 0.037(2) Uani 1 1 d . . . . .
C2 C 0.6033(10) 0.7554(8) 0.0603(5) 0.039(2) Uani 1 1 d . . . . .
H2 H 0.622515 0.777130 0.020977 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6312(10) 0.6726(9) 0.0763(5) 0.041(3) Uani 1 1 d . . . . .
H3 H 0.672658 0.638154 0.048295 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5999(11) 0.6373(9) 0.1335(5) 0.044(3) Uani 1 1 d . . . . .
H4 H 0.615639 0.578194 0.144293 0.052 Uiso 1 1 calc R U . . .
C5 C 0.5436(9) 0.6951(7) 0.1740(5) 0.033(2) Uani 1 1 d . . . . .
H5 H 0.522828 0.674805 0.213502 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5110(10) 0.8946(8) 0.0894(5) 0.036(2) Uani 1 1 d . . . . .
C7 C 0.4058(9) 1.0080(7) 0.1373(5) 0.0319(19) Uani 1 1 d . U . . .
C8 C 0.3595(9) 1.0339(7) 0.1971(5) 0.0319(19) Uani 1 1 d . U . . .
C9 C 0.3074(9) 1.1133(7) 0.2121(5) 0.035(2) Uani 1 1 d . . . . .
H9 H 0.296754 1.153922 0.181285 0.042 Uiso 1 1 calc R U . . .
C10 C 0.2728(11) 1.1317(8) 0.2698(5) 0.038(2) Uani 1 1 d . . . . .
H10 H 0.237904 1.185050 0.280215 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2892(11) 1.0714(8) 0.3136(6) 0.041(3) Uani 1 1 d . . . . .
H11 H 0.266088 1.082833 0.354802 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3400(9) 0.9937(7) 0.2966(5) 0.034(2) Uani 1 1 d . . . . .
H12 H 0.352100 0.953377 0.327295 0.041 Uiso 1 1 calc R U . . .
C13 C 0.1996(9) 0.6972(7) 0.2295(4) 0.0267(19) Uani 1 1 d . . . . .
C14 C 0.0688(9) 0.6211(7) 0.2204(5) 0.029(2) Uani 1 1 d . . . . .
H14 H 0.036925 0.580561 0.252148 0.035 Uiso 1 1 calc R U . . .
C15 C -0.0170(10) 0.6049(7) 0.1626(5) 0.035(2) Uani 1 1 d . . . . .
H15 H -0.108212 0.553298 0.154663 0.041 Uiso 1 1 calc R U . . .
C16 C 0.0343(10) 0.6654(8) 0.1181(5) 0.033(2) Uani 1 1 d . . . . .
H16 H -0.021696 0.655116 0.078788 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1673(10) 0.7416(8) 0.1300(4) 0.033(2) Uani 1 1 d . . . . .
H17 H 0.200180 0.783027 0.098810 0.039 Uiso 1 1 calc R U . . .
C18 C 0.3032(9) 0.7205(7) 0.2855(4) 0.0241(19) Uani 1 1 d . . . . .
C19 C 0.5309(9) 0.8240(7) 0.3277(4) 0.0228(18) Uani 1 1 d . . . . .
C20 C 0.6512(9) 0.9078(7) 0.3170(4) 0.0254(19) Uani 1 1 d . . . . .
C21 C 0.7749(9) 0.9529(7) 0.3576(4) 0.0272(19) Uani 1 1 d . . . . .
H26 H 0.787092 0.927803 0.395741 0.033 Uiso 1 1 calc R U . . .
C22 C 0.8806(10) 1.0351(7) 0.3419(5) 0.034(2) Uani 1 1 d . . . . .
H27 H 0.967933 1.065300 0.368140 0.040 Uiso 1 1 calc R U . . .
C23 C 0.8575(10) 1.0736(8) 0.2865(5) 0.034(2) Uani 1 1 d . . . . .
H28 H 0.927414 1.132113 0.275863 0.041 Uiso 1 1 calc R U . . .
C24 C 0.7292(9) 1.0242(7) 0.2471(5) 0.030(2) Uani 1 1 d . . . . .
H29 H 0.714061 1.049603 0.209395 0.035 Uiso 1 1 calc R U . . .
C25 C 0.3956(9) 0.7036(7) 0.3787(4) 0.0255(19) Uani 1 1 d . . . . .
C26 C 0.3831(10) 0.6544(7) 0.4359(5) 0.032(2) Uani 1 1 d . . . . .
C27 C 0.4943(11) 0.6644(8) 0.4792(5) 0.036(2) Uani 1 1 d . . . . .
H20 H 0.586649 0.706433 0.474760 0.044 Uiso 1 1 calc R U . . .
C28 C 0.4666(14) 0.6105(9) 0.5300(5) 0.049(3) Uani 1 1 d . . . . .
H21 H 0.542104 0.615874 0.560233 0.058 Uiso 1 1 calc R U . . .
C29 C 0.3368(13) 0.5517(9) 0.5374(5) 0.047(3) Uani 1 1 d . . . . .
H22 H 0.320233 0.515330 0.572037 0.056 Uiso 1 1 calc R U . . .
C30 C 0.2277(12) 0.5450(8) 0.4934(5) 0.043(3) Uani 1 1 d . . . . .
H23 H 0.134805 0.504873 0.498226 0.052 Uiso 1 1 calc R U . . .
O1 O -0.0204(8) 0.5186(7) 0.3884(4) 0.052(2) Uani 1 1 d D . . . .
H1O1 H -0.042(12) 0.456(4) 0.367(5) 0.062 Uiso 1 1 d D U . . .
H2O1 H -0.073(10) 0.546(7) 0.369(5) 0.062 Uiso 1 1 d D U . . .
O2 O 0.2789(8) 1.2105(6) 0.0762(4) 0.0424(18) Uani 1 1 d D . . . .
H1O2 H 0.195(4) 1.201(7) 0.060(5) 0.051 Uiso 1 1 d D U . . .
H2O2 H 0.328(8) 1.2765(18) 0.084(5) 0.051 Uiso 1 1 d D U . . .


_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
I3 I4 2.8551(9) . ?
I4 I5 3.0449(9) . ?
I6 I7 2.7534(10) . ?
I8 I9 2.9192(11) . ?
I9 I10 2.9006(11) . ?
I11 I12 2.7449(11) . ?
I13 I14 2.7405(11) . ?
I15 I16 2.8286(10) . ?
I16 I17 3.0456(10) . ?
I18 I18 2.7985(16) 2_456 ?
Fe1 N1 1.965(8) . ?
Fe1 N2 1.943(8) . ?
Fe1 N3 1.984(8) . ?
Fe1 N5 1.987(7) . ?
Fe1 N6 1.837(7) . ?
Fe1 N7 1.993(7) . ?
O4 C6 1.257(12) . ?
N1 C1 1.386(13) . ?
N1 C5 1.303(13) . ?
N2 C6 1.358(13) . ?
N2 C7 1.347(13) . ?
N3 C8 1.352(11) . ?
N3 C12 1.339(13) . ?
N4 HN4A 0.8800 . ?
N4 HN4B 0.8800 . ?
N4 C7 1.296(12) . ?
N5 C13 1.382(11) . ?
N5 C17 1.347(11) . ?
N6 C18 1.336(11) . ?
N6 C19 1.376(11) . ?
N7 C20 1.392(11) . ?
N7 C24 1.330(11) . ?
N8 C18 1.325(11) . ?
N8 C25 1.325(12) . ?
N9 C19 1.335(11) . ?
N9 C25 1.357(11) . ?
N10 HN10 0.86(2) . ?
N10 C26 1.358(13) . ?
N10 C30 1.338(13) . ?
C1 C2 1.370(14) . ?
C1 C6 1.452(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.365(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.418(15) . ?
C5 H5 0.9500 . ?
C7 C8 1.464(15) . ?
C8 C9 1.412(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.347(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(12) . ?
C13 C18 1.467(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.414(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(14) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(13) . ?
C17 H17 0.9500 . ?
C19 C20 1.436(12) . ?
C20 C21 1.382(12) . ?
C21 H26 0.9500 . ?
C21 C22 1.380(13) . ?
C22 H27 0.9500 . ?
C22 C23 1.406(14) . ?
C23 H28 0.9500 . ?
C23 C24 1.407(13) . ?
C24 H29 0.9500 . ?
C25 C26 1.478(13) . ?
C26 C27 1.375(14) . ?
C27 H20 0.9500 . ?
C27 C28 1.400(15) . ?
C28 H21 0.9500 . ?
C28 C29 1.341(17) . ?
C29 H22 0.9500 . ?
C29 C30 1.382(16) . ?
C30 H23 0.9500 . ?
O1 H1O1 0.87(2) . ?
O1 H2O1 0.87(2) . ?
O2 H1O2 0.868(10) . ?
O2 H2O2 0.868(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
I3 I4 I5 172.79(3) . . ?
I10 I9 I8 174.40(3) . . ?
I15 I16 I17 174.51(4) . . ?
N1 Fe1 N3 161.6(3) . . ?
N1 Fe1 N5 91.0(3) . . ?
N1 Fe1 N7 91.7(3) . . ?
N2 Fe1 N1 82.5(3) . . ?
N2 Fe1 N3 79.2(3) . . ?
N2 Fe1 N5 98.4(3) . . ?
N2 Fe1 N7 100.5(3) . . ?
N3 Fe1 N5 92.3(3) . . ?
N3 Fe1 N7 91.0(3) . . ?
N5 Fe1 N7 161.2(3) . . ?
N6 Fe1 N1 98.9(3) . . ?
N6 Fe1 N2 178.0(3) . . ?
N6 Fe1 N3 99.5(3) . . ?
N6 Fe1 N5 80.1(3) . . ?
N6 Fe1 N7 81.1(3) . . ?
C1 N1 Fe1 113.0(7) . . ?
C5 N1 Fe1 126.4(7) . . ?
C5 N1 C1 120.6(9) . . ?
C6 N2 Fe1 116.1(7) . . ?
C7 N2 Fe1 118.1(7) . . ?
C7 N2 C6 125.6(8) . . ?
C8 N3 Fe1 117.0(7) . . ?
C12 N3 Fe1 125.9(6) . . ?
C12 N3 C8 117.0(8) . . ?
HN4A N4 HN4B 120.0 . . ?
C7 N4 HN4A 120.0 . . ?
C7 N4 HN4B 120.0 . . ?
C13 N5 Fe1 114.4(6) . . ?
C17 N5 Fe1 127.7(6) . . ?
C17 N5 C13 117.9(8) . . ?
C18 N6 Fe1 122.4(6) . . ?
C18 N6 C19 117.6(7) . . ?
C19 N6 Fe1 120.0(6) . . ?
C20 N7 Fe1 114.0(6) . . ?
C24 N7 Fe1 127.6(6) . . ?
C24 N7 C20 118.4(8) . . ?
C18 N8 C25 114.7(7) . . ?
C19 N9 C25 113.4(7) . . ?
C26 N10 HN10 121(10) . . ?
C30 N10 HN10 115(10) . . ?
C30 N10 C26 121.6(10) . . ?
N1 C1 C6 115.3(9) . . ?
C2 C1 N1 120.4(10) . . ?
C2 C1 C6 124.3(10) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(11) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(10) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 121.9 . . ?
C3 C4 C5 116.2(10) . . ?
C5 C4 H4 121.9 . . ?
N1 C5 C4 122.3(10) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
O4 C6 N2 124.9(10) . . ?
O4 C6 C1 122.1(10) . . ?
N2 C6 C1 113.1(9) . . ?
N2 C7 C8 113.0(8) . . ?
N4 C7 N2 124.9(10) . . ?
N4 C7 C8 122.1(9) . . ?
N3 C8 C7 112.3(9) . . ?
N3 C8 C9 121.5(10) . . ?
C9 C8 C7 126.2(9) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(10) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(10) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.0(11) . . ?
C12 C11 H11 120.5 . . ?
N3 C12 C11 123.4(10) . . ?
N3 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
N5 C13 C18 112.0(7) . . ?
C14 C13 N5 123.0(8) . . ?
C14 C13 C18 124.9(8) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.3(9) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.6(8) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(9) . . ?
C17 C16 H16 119.7 . . ?
N5 C17 C16 121.7(9) . . ?
N5 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
N6 C18 C13 110.9(8) . . ?
N8 C18 N6 123.6(8) . . ?
N8 C18 C13 125.5(8) . . ?
N6 C19 C20 112.5(7) . . ?
N9 C19 N6 122.7(8) . . ?
N9 C19 C20 124.8(8) . . ?
N7 C20 C19 112.3(7) . . ?
C21 C20 N7 122.4(8) . . ?
C21 C20 C19 125.3(8) . . ?
C20 C21 H26 120.5 . . ?
C22 C21 C20 118.9(9) . . ?
C22 C21 H26 120.5 . . ?
C21 C22 H27 120.4 . . ?
C21 C22 C23 119.3(8) . . ?
C23 C22 H27 120.4 . . ?
C22 C23 H28 120.5 . . ?
C22 C23 C24 119.0(9) . . ?
C24 C23 H28 120.5 . . ?
N7 C24 C23 122.0(9) . . ?
N7 C24 H29 119.0 . . ?
C23 C24 H29 119.0 . . ?
N8 C25 N9 128.0(8) . . ?
N8 C25 C26 117.9(8) . . ?
N9 C25 C26 114.0(8) . . ?
N10 C26 C25 116.1(9) . . ?
N10 C26 C27 119.8(9) . . ?
C27 C26 C25 124.1(9) . . ?
C26 C27 H20 121.2 . . ?
C26 C27 C28 117.7(10) . . ?
C28 C27 H20 121.2 . . ?
C27 C28 H21 119.0 . . ?
C29 C28 C27 122.0(11) . . ?
C29 C28 H21 119.0 . . ?
C28 C29 H22 120.7 . . ?
C28 C29 C30 118.5(11) . . ?
C30 C29 H22 120.7 . . ?
N10 C30 C29 120.4(10) . . ?
N10 C30 H23 119.8 . . ?
C29 C30 H23 119.8 . . ?
H1O1 O1 H2O1 106(5) . . ?
H1O2 O2 H2O2 109(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 N1 C1 C2 178.9(7) . . . . ?
Fe1 N1 C1 C6 -1.9(10) . . . . ?
Fe1 N1 C5 C4 -179.7(7) . . . . ?
Fe1 N2 C6 O4 -179.9(8) . . . . ?
Fe1 N2 C6 C1 0.3(10) . . . . ?
Fe1 N2 C7 N4 -175.5(7) . . . . ?
Fe1 N2 C7 C8 6.8(10) . . . . ?
Fe1 N3 C8 C7 -2.2(9) . . . . ?
Fe1 N3 C8 C9 178.4(7) . . . . ?
Fe1 N3 C12 C11 -178.9(7) . . . . ?
Fe1 N5 C13 C14 179.8(7) . . . . ?
Fe1 N5 C13 C18 -2.9(9) . . . . ?
Fe1 N5 C17 C16 -180.0(7) . . . . ?
Fe1 N6 C18 N8 -178.1(6) . . . . ?
Fe1 N6 C18 C13 2.7(10) . . . . ?
Fe1 N6 C19 N9 179.5(6) . . . . ?
Fe1 N6 C19 C20 1.2(10) . . . . ?
Fe1 N7 C20 C19 -3.4(9) . . . . ?
Fe1 N7 C20 C21 178.8(7) . . . . ?
Fe1 N7 C24 C23 -178.9(7) . . . . ?
N1 Fe1 N6 C18 -92.9(7) . . . . ?
N1 Fe1 N6 C19 87.9(7) . . . . ?
N1 C1 C2 C3 0.1(14) . . . . ?
N1 C1 C6 O4 -178.8(9) . . . . ?
N1 C1 C6 N2 1.1(12) . . . . ?
N2 C7 C8 N3 -2.8(11) . . . . ?
N2 C7 C8 C9 176.5(8) . . . . ?
N3 Fe1 N6 C18 87.2(7) . . . . ?
N3 Fe1 N6 C19 -92.0(7) . . . . ?
N3 C8 C9 C10 1.7(14) . . . . ?
N4 C7 C8 N3 179.4(8) . . . . ?
N4 C7 C8 C9 -1.2(14) . . . . ?
N5 Fe1 N6 C18 -3.5(7) . . . . ?
N5 Fe1 N6 C19 177.4(7) . . . . ?
N5 C13 C14 C15 -0.2(14) . . . . ?
N5 C13 C18 N6 0.4(11) . . . . ?
N5 C13 C18 N8 -178.8(8) . . . . ?
N6 C19 C20 N7 1.6(11) . . . . ?
N6 C19 C20 C21 179.3(8) . . . . ?
N7 Fe1 N6 C18 176.7(7) . . . . ?
N7 Fe1 N6 C19 -2.4(6) . . . . ?
N7 C20 C21 C22 -0.7(14) . . . . ?
N8 C25 C26 N10 -10.7(12) . . . . ?
N8 C25 C26 C27 168.3(9) . . . . ?
N9 C19 C20 N7 -176.6(8) . . . . ?
N9 C19 C20 C21 1.0(15) . . . . ?
N9 C25 C26 N10 166.5(8) . . . . ?
N9 C25 C26 C27 -14.6(13) . . . . ?
N10 C26 C27 C28 0.9(14) . . . . ?
C1 N1 C5 C4 0.5(14) . . . . ?
C1 C2 C3 C4 1.8(15) . . . . ?
C2 C1 C6 O4 0.4(15) . . . . ?
C2 C1 C6 N2 -179.8(9) . . . . ?
C2 C3 C4 C5 -2.5(15) . . . . ?
C3 C4 C5 N1 1.3(14) . . . . ?
C5 N1 C1 C2 -1.3(14) . . . . ?
C5 N1 C1 C6 177.9(8) . . . . ?
C6 N2 C7 N4 -0.6(15) . . . . ?
C6 N2 C7 C8 -178.3(8) . . . . ?
C6 C1 C2 C3 -179.0(9) . . . . ?
C7 N2 C6 O4 5.1(15) . . . . ?
C7 N2 C6 C1 -174.8(8) . . . . ?
C7 C8 C9 C10 -177.6(9) . . . . ?
C8 N3 C12 C11 2.4(13) . . . . ?
C8 C9 C10 C11 -0.1(15) . . . . ?
C9 C10 C11 C12 -0.3(15) . . . . ?
C10 C11 C12 N3 -0.9(15) . . . . ?
C12 N3 C8 C7 176.6(8) . . . . ?
C12 N3 C8 C9 -2.8(12) . . . . ?
C13 N5 C17 C16 -0.6(14) . . . . ?
C13 C14 C15 C16 0.3(14) . . . . ?
C14 C13 C18 N6 177.6(9) . . . . ?
C14 C13 C18 N8 -1.6(15) . . . . ?
C14 C15 C16 C17 -0.6(15) . . . . ?
C15 C16 C17 N5 0.8(16) . . . . ?
C17 N5 C13 C14 0.3(14) . . . . ?
C17 N5 C13 C18 177.6(8) . . . . ?
C18 N6 C19 N9 0.3(12) . . . . ?
C18 N6 C19 C20 -178.0(8) . . . . ?
C18 N8 C25 N9 3.4(13) . . . . ?
C18 N8 C25 C26 -179.9(8) . . . . ?
C18 C13 C14 C15 -177.1(9) . . . . ?
C19 N6 C18 N8 1.1(13) . . . . ?
C19 N6 C18 C13 -178.1(7) . . . . ?
C19 N9 C25 N8 -2.2(13) . . . . ?
C19 N9 C25 C26 -179.0(7) . . . . ?
C19 C20 C21 C22 -178.2(9) . . . . ?
C20 N7 C24 C23 1.2(14) . . . . ?
C20 C21 C22 C23 2.8(14) . . . . ?
C21 C22 C23 C24 -2.9(15) . . . . ?
C22 C23 C24 N7 0.9(15) . . . . ?
C24 N7 C20 C19 176.4(8) . . . . ?
C24 N7 C20 C21 -1.3(13) . . . . ?
C25 N8 C18 N6 -2.7(12) . . . . ?
C25 N8 C18 C13 176.3(8) . . . . ?
C25 N9 C19 N6 0.2(12) . . . . ?
C25 N9 C19 C20 178.2(8) . . . . ?
C25 C26 C27 C28 -178.0(9) . . . . ?
C26 N10 C30 C29 -1.1(15) . . . . ?
C26 C27 C28 C29 -0.6(16) . . . . ?
C27 C28 C29 C30 -0.4(17) . . . . ?
C28 C29 C30 N10 1.3(16) . . . . ?
C30 N10 C26 C25 179.0(9) . . . . ?
C30 N10 C26 C27 0.0(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT434_27jul20_ajp3_xprep_a 
;
PROBLEM: Short Inter HL..HL Contact I8       ..I14      .       3.25 Ang.  
RESPONSE: This contact represents an I...I halogen bond
;
_vrf_PLAT420_27jul20_ajp3_xprep_a 
;
PROBLEM: D-H Bond Without Acceptor  O1       --H1O1     .     Please Check 
RESPONSE: This water molecule acts as both an N-H...O acceptor and O-H...I donor
;
####################################################################### 
# 
# 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_mo_d8_5046_14mar21_ajp1_0m
_database_code_depnum_ccdc_archive 'CCDC 2182012'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(I3), 4(C10 H9 N6), 3(C2 H3 N)'
_chemical_formula_sum            'C46 H45 I12 N27'
_chemical_formula_weight         2498.89
_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'

_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                   13.5105(5)
_cell_length_b                   14.6827(7)
_cell_length_c                   17.4311(8)
_cell_angle_alpha                93.901(2)
_cell_angle_beta                 101.189(2)
_cell_angle_gamma                91.407(2)
_cell_volume                     3381.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.615
_shelx_estimated_absorpt_T_min   0.422
_exptl_absorpt_coefficient_mu    5.550
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.454
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2292
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.097
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            143131
_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         27.877
_diffrn_reflns_theta_min         2.113
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                13684
_reflns_number_total             16112
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         1.465
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     817
_refine_ls_number_reflns         16112
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+9.9264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0567
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 HN3-N3
 0.86 with sigma of 0.02
 HN7B-N7
 0.86 with sigma of 0.02
 HN15-N15
 0.86 with sigma of 0.02
 HN19-N19
 0.86 with sigma of 0.02
 N19-H2
 0.86 with sigma of 0.02
 HN7A-N7
 0.86 with sigma of 0.02
 HN9-N9
 0.86 with sigma of 0.02
 HN13-N13
 0.86 with sigma of 0.02
 H1-N13
 0.86 with sigma of 0.02
 N21-HN21
 0.86 with sigma of 0.02
2. Restrained planarity
 N3, HN3, C3, C4
 with sigma of 0.1
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C7(H7), C8(H8), C9(H9), C44(H44), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C46(H46), C20(H20), C21(H21A), C22(H22),
 C25(H25), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), C35(H35), C36(H36),
  C37(H37)
3.b Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C43(H43A,H43B,H43C)
;
_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
I1 I 0.86100(2) 0.06915(2) 0.60307(2) 0.01906(5) Uani 1 1 d . . . . .
I2 I 0.86361(2) 0.04408(2) 0.43604(2) 0.01749(5) Uani 1 1 d . . . . .
I3 I 0.87008(2) 0.01960(2) 0.26874(2) 0.01989(5) Uani 1 1 d . . . . .
I4 I 0.58652(2) 0.14605(2) 0.46354(2) 0.02356(5) Uani 1 1 d . . . . .
I5 I 0.59745(2) 0.13966(2) 0.29500(2) 0.02064(5) Uani 1 1 d . . . . .
I6 I 0.61490(2) 0.13089(2) 0.13210(2) 0.02455(6) Uani 1 1 d . . . . .
I7 I 0.31097(2) 0.54608(2) 0.08248(2) 0.02664(6) Uani 1 1 d . . . . .
I8 I 0.34318(2) 0.74518(2) 0.08372(2) 0.02286(5) Uani 1 1 d . . . . .
I9 I 0.37707(2) 0.94233(2) 0.09695(2) 0.03036(6) Uani 1 1 d . . . . .
I10 I 1.05096(2) 0.65150(2) -0.03293(2) 0.02442(6) Uani 1 1 d . . . . .
I11 I 0.86502(2) 0.72654(2) -0.11850(2) 0.02158(5) Uani 1 1 d . . . . .
I12 I 0.67838(2) 0.79566(2) -0.20718(2) 0.02627(6) Uani 1 1 d . . . . .
N1 N 0.8449(3) 0.3018(2) 0.5276(2) 0.0257(7) Uani 1 1 d . . . . .
HN1B H 0.843(3) 0.255(3) 0.544(3) 0.018(11) Uiso 1 1 d . . . . .
HN1A H 0.838(4) 0.305(3) 0.478(3) 0.033(13) Uiso 1 1 d . . . . .
N2 N 0.9021(2) 0.4762(2) 0.68344(18) 0.0170(6) Uani 1 1 d . . . . .
N3 N 0.8916(2) 0.3516(2) 0.7922(2) 0.0215(7) Uani 1 1 d D . . . .
HN3 H 0.885(3) 0.309(3) 0.822(3) 0.042(15) Uiso 1 1 d D . . . .
N4 N 0.8792(2) 0.4598(2) 0.55250(19) 0.0189(6) Uani 1 1 d . . . . .
N5 N 0.9234(2) 0.6707(2) 0.67955(19) 0.0207(6) Uani 1 1 d . . . . .
N6 N 0.9165(2) 0.7433(2) 0.53368(19) 0.0194(6) Uani 1 1 d . . . . .
C1 C 0.8682(3) 0.3757(2) 0.5774(2) 0.0183(7) Uani 1 1 d . . . . .
C2 C 0.8821(3) 0.3814(2) 0.6609(2) 0.0181(7) Uani 1 1 d . . . . .
C3 C 0.8774(3) 0.3215(2) 0.7168(2) 0.0192(7) Uani 1 1 d . . . . .
H3A H 0.863975 0.258247 0.701969 0.023 Uiso 1 1 calc R U . . .
C4 C 0.9130(3) 0.4434(3) 0.8155(2) 0.0221(8) Uani 1 1 d . . . . .
H4 H 0.923670 0.462934 0.869642 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8990(3) 0.5188(2) 0.6171(2) 0.0168(7) Uani 1 1 d . . . . .
C6 C 0.9110(3) 0.6174(2) 0.6125(2) 0.0165(7) Uani 1 1 d . . . . .
C7 C 0.9082(3) 0.6532(2) 0.5399(2) 0.0192(7) Uani 1 1 d . . . . .
H7 H 0.900245 0.612748 0.494069 0.023 Uiso 1 1 calc R U . . .
C8 C 0.9283(3) 0.7965(2) 0.6007(2) 0.0210(8) Uani 1 1 d . . . . .
H8 H 0.934832 0.860844 0.598927 0.025 Uiso 1 1 calc R U . . .
C9 C 0.9314(3) 0.7607(2) 0.6722(2) 0.0220(8) Uani 1 1 d . . . . .
H9 H 0.939492 0.801392 0.717975 0.026 Uiso 1 1 calc R U . . .
C44 C 0.9190(3) 0.5050(2) 0.7633(2) 0.0195(7) Uani 1 1 d . . . . .
H44 H 0.934453 0.567542 0.780131 0.023 Uiso 1 1 calc R U . . .
N7 N 0.5895(3) 0.3822(2) 0.4092(2) 0.0273(7) Uani 1 1 d D . . . .
HN7B H 0.584(4) 0.3271(17) 0.421(3) 0.034(13) Uiso 1 1 d D . . . .
HN7A H 0.581(3) 0.390(3) 0.3600(12) 0.020(11) Uiso 1 1 d D . . . .
N8 N 0.6455(2) 0.5502(2) 0.57036(19) 0.0211(7) Uani 1 1 d . . . . .
N9 N 0.6370(3) 0.4181(2) 0.6731(2) 0.0265(7) Uani 1 1 d D . . . .
HN9 H 0.629(4) 0.376(3) 0.704(3) 0.046(15) Uiso 1 1 d D . . . .
N10 N 0.6208(2) 0.5408(2) 0.4391(2) 0.0217(7) Uani 1 1 d . . . . .
N11 N 0.6803(2) 0.7437(2) 0.57440(19) 0.0233(7) Uani 1 1 d . . . . .
N12 N 0.6494(3) 0.8269(2) 0.4325(2) 0.0257(7) Uani 1 1 d . . . . .
C10 C 0.6122(3) 0.4544(3) 0.4610(2) 0.0213(8) Uani 1 1 d . . . . .
C11 C 0.6260(3) 0.4561(2) 0.5440(2) 0.0211(8) Uani 1 1 d . . . . .
C12 C 0.6224(3) 0.3924(3) 0.5963(2) 0.0235(8) Uani 1 1 d . . . . .
H12 H 0.609585 0.329805 0.578571 0.028 Uiso 1 1 calc R U . . .
C13 C 0.6553(3) 0.5092(3) 0.7000(2) 0.0271(9) Uani 1 1 d . . . . .
H13 H 0.664834 0.525563 0.754721 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6542(3) 0.6954(3) 0.5054(2) 0.0201(7) Uani 1 1 d . . . . .
C15 C 0.6401(3) 0.7364(3) 0.4346(2) 0.0246(8) Uani 1 1 d . . . . .
H15 H 0.623555 0.699174 0.386849 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6734(3) 0.8759(3) 0.5013(2) 0.0249(8) Uani 1 1 d . . . . .
H16 H 0.679863 0.940601 0.502158 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6892(3) 0.8344(3) 0.5715(2) 0.0249(8) Uani 1 1 d . . . . .
H17 H 0.707082 0.871533 0.619197 0.030 Uiso 1 1 calc R U . . .
C45 C 0.6409(3) 0.5961(2) 0.5051(2) 0.0192(7) Uani 1 1 d . . . . .
C46 C 0.6600(3) 0.5747(3) 0.6506(2) 0.0242(8) Uani 1 1 d . . . . .
H46 H 0.673008 0.636760 0.669999 0.029 Uiso 1 1 calc R U . . .
N13 N 0.6321(3) 0.8794(2) 0.2698(2) 0.0270(7) Uani 1 1 d D . . . .
HN13 H 0.640(4) 0.871(3) 0.3199(13) 0.037(14) Uiso 1 1 d D . . . .
H1 H 0.649(4) 0.931(2) 0.255(3) 0.043(15) Uiso 1 1 d D . . . .
N14 N 0.6164(2) 0.7082(2) 0.11259(19) 0.0199(6) Uani 1 1 d . . . . .
N15 N 0.6246(3) 0.8383(3) 0.0091(2) 0.0305(8) Uani 1 1 d D . . . .
HN15 H 0.625(4) 0.881(3) -0.023(3) 0.048(16) Uiso 1 1 d D . . . .
N16 N 0.6171(2) 0.7202(2) 0.24127(19) 0.0197(6) Uani 1 1 d . . . . .
N17 N 0.6012(2) 0.5123(2) 0.1113(2) 0.0226(7) Uani 1 1 d . . . . .
N18 N 0.5725(3) 0.4356(2) 0.2485(2) 0.0239(7) Uani 1 1 d . . . . .
C18 C 0.6257(3) 0.8057(3) 0.2191(2) 0.0222(8) Uani 1 1 d . . . . .
C19 C 0.6256(3) 0.8026(3) 0.1372(2) 0.0217(8) Uani 1 1 d . . . . .
C20 C 0.6290(3) 0.8658(3) 0.0838(3) 0.0260(8) Uani 1 1 d . . . . .
H20 H 0.634515 0.929162 0.100080 0.031 Uiso 1 1 calc R U . . .
C21 C 0.6144(3) 0.7461(3) -0.0163(3) 0.0292(9) Uani 1 1 d . . . . .
H21A H 0.610120 0.728538 -0.070349 0.035 Uiso 1 1 calc R U . . .
C22 C 0.6105(3) 0.6819(3) 0.0333(2) 0.0244(8) Uani 1 1 d . . . . .
H22 H 0.603869 0.619159 0.015148 0.029 Uiso 1 1 calc R U . . .
C23 C 0.6110(3) 0.6632(2) 0.1766(2) 0.0194(7) Uani 1 1 d . . . . .
C24 C 0.5987(3) 0.5642(2) 0.1773(2) 0.0175(7) Uani 1 1 d . . . . .
C25 C 0.5861(3) 0.5259(2) 0.2460(2) 0.0216(8) Uani 1 1 d . . . . .
H25 H 0.587202 0.564734 0.292095 0.026 Uiso 1 1 calc R U . . .
C26 C 0.5716(3) 0.3843(3) 0.1819(2) 0.0243(8) Uani 1 1 d . . . . .
H26 H 0.559590 0.320162 0.180706 0.029 Uiso 1 1 calc R U . . .
C27 C 0.5878(3) 0.4225(3) 0.1145(2) 0.0252(8) Uani 1 1 d . . . . .
H27 H 0.589293 0.383301 0.069147 0.030 Uiso 1 1 calc R U . . .
N19 N 0.8895(3) 0.7877(2) 0.3666(2) 0.0241(7) Uani 1 1 d D . . . .
HN19 H 0.897(3) 0.784(3) 0.4152(12) 0.024(12) Uiso 1 1 d D . . . .
H2 H 0.901(3) 0.8390(18) 0.351(3) 0.027(12) Uiso 1 1 d D . . . .
N20 N 0.8512(2) 0.61046(19) 0.21265(18) 0.0171(6) Uani 1 1 d . . . . .
N21 N 0.8648(2) 0.7351(2) 0.10461(19) 0.0212(7) Uani 1 1 d D . . . .
HN21 H 0.867(4) 0.773(3) 0.069(2) 0.046(16) Uiso 1 1 d D . . . .
N22 N 0.8640(2) 0.6281(2) 0.34301(19) 0.0178(6) Uani 1 1 d . . . . .
N23 N 0.8312(2) 0.4160(2) 0.21735(19) 0.0203(6) Uani 1 1 d . . . . .
N24 N 0.8309(2) 0.3443(2) 0.3618(2) 0.0213(7) Uani 1 1 d . . . . .
C28 C 0.8741(3) 0.7125(2) 0.3180(2) 0.0167(7) Uani 1 1 d . . . . .
C29 C 0.8668(3) 0.7056(2) 0.2350(2) 0.0165(7) Uani 1 1 d . . . . .
C30 C 0.8739(3) 0.7653(2) 0.1794(2) 0.0194(7) Uani 1 1 d . . . . .
H30 H 0.885404 0.828701 0.194197 0.023 Uiso 1 1 calc R U . . .
C31 C 0.8476(3) 0.6427(2) 0.0815(2) 0.0197(7) Uani 1 1 d . . . . .
H31 H 0.840834 0.622916 0.027605 0.024 Uiso 1 1 calc R U . . .
C32 C 0.8405(3) 0.5811(2) 0.1334(2) 0.0190(7) Uani 1 1 d . . . . .
H32 H 0.828299 0.518164 0.116643 0.023 Uiso 1 1 calc R U . . .
C33 C 0.8503(3) 0.5685(2) 0.2790(2) 0.0167(7) Uani 1 1 d . . . . .
C34 C 0.8390(3) 0.4702(2) 0.2838(2) 0.0173(7) Uani 1 1 d . . . . .
C35 C 0.8381(3) 0.4345(2) 0.3554(2) 0.0192(7) Uani 1 1 d . . . . .
H35 H 0.842720 0.474975 0.401010 0.023 Uiso 1 1 calc R U . . .
C36 C 0.8232(3) 0.2907(2) 0.2958(2) 0.0202(7) Uani 1 1 d . . . . .
H36 H 0.817440 0.226330 0.297817 0.024 Uiso 1 1 calc R U . . .
C37 C 0.8236(3) 0.3265(2) 0.2243(2) 0.0239(8) Uani 1 1 d . . . . .
H37 H 0.818235 0.285796 0.178776 0.029 Uiso 1 1 calc R U . . .
N25 N 0.8953(3) 0.1674(2) 0.8340(2) 0.0327(8) Uani 1 1 d . . . . .
C38 C 0.8857(3) 0.0911(3) 0.8293(2) 0.0241(8) Uani 1 1 d . . . . .
C39 C 0.8736(4) -0.0088(3) 0.8237(3) 0.0341(10) Uani 1 1 d . . . . .
H39A H 0.921820 -0.035268 0.793907 0.051 Uiso 1 1 calc R U . . .
H39B H 0.804705 -0.027257 0.796945 0.051 Uiso 1 1 calc R U . . .
H39C H 0.886404 -0.030611 0.876484 0.051 Uiso 1 1 calc R U . . .
N26 N 0.6295(3) 0.2302(3) 0.6996(2) 0.0419(10) Uani 1 1 d . . . . .
C40 C 0.6131(3) 0.1540(3) 0.6873(2) 0.0294(9) Uani 1 1 d . . . . .
C41 C 0.5916(4) 0.0564(3) 0.6702(3) 0.0331(10) Uani 1 1 d . . . . .
H41A H 0.641196 0.030545 0.641461 0.050 Uiso 1 1 calc R U . . .
H41B H 0.523667 0.046073 0.638198 0.050 Uiso 1 1 calc R U . . .
H41C H 0.595605 0.026911 0.719402 0.050 Uiso 1 1 calc R U . . .
N27 N 0.8750(3) 0.9207(2) 0.0519(2) 0.0326(8) Uani 1 1 d . . . . .
C42 C 0.8775(3) 0.9974(3) 0.0501(2) 0.0258(8) Uani 1 1 d . . . . .
C43 C 0.8815(3) 1.0976(3) 0.0496(3) 0.0316(9) Uani 1 1 d . . . . .
H43A H 0.823757 1.116883 0.011775 0.047 Uiso 1 1 calc R U . . .
H43B H 0.944380 1.117548 0.034524 0.047 Uiso 1 1 calc R U . . .
H43C H 0.879160 1.124951 0.101997 0.047 Uiso 1 1 calc R U . . .


_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
I1 I2 2.9169(4) . ?
I2 I3 2.9325(4) . ?
I4 I5 2.9653(4) . ?
I5 I6 2.8890(4) . ?
I7 I8 2.9429(4) . ?
I8 I9 2.9061(4) . ?
I10 I11 2.9419(4) . ?
I11 I12 2.9333(4) . ?
N1 HN1B 0.75(5) . ?
N1 HN1A 0.86(5) . ?
N1 C1 1.335(5) . ?
N2 C2 1.425(4) . ?
N2 C5 1.345(5) . ?
N2 C44 1.400(5) . ?
N3 HN3 0.851(19) . ?
N3 C3 1.333(5) . ?
N3 C4 1.388(5) . ?
N4 C1 1.350(4) . ?
N4 C5 1.353(5) . ?
N5 C6 1.342(5) . ?
N5 C9 1.340(5) . ?
N6 C7 1.339(4) . ?
N6 C8 1.341(5) . ?
C1 C2 1.426(5) . ?
C2 C3 1.367(5) . ?
C3 H3A 0.9500 . ?
C4 H4 0.9500 . ?
C4 C44 1.338(5) . ?
C5 C6 1.463(5) . ?
C6 C7 1.395(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.378(5) . ?
C9 H9 0.9500 . ?
C44 H44 0.9500 . ?
N7 HN7B 0.855(19) . ?
N7 HN7A 0.859(19) . ?
N7 C10 1.334(5) . ?
N8 C11 1.427(5) . ?
N8 C45 1.353(5) . ?
N8 C46 1.395(5) . ?
N9 HN9 0.861(19) . ?
N9 C12 1.342(5) . ?
N9 C13 1.387(5) . ?
N10 C10 1.357(5) . ?
N10 C45 1.342(5) . ?
N11 C14 1.334(5) . ?
N11 C17 1.339(5) . ?
N12 C15 1.336(5) . ?
N12 C16 1.335(5) . ?
C10 C11 1.421(5) . ?
C11 C12 1.357(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C46 1.343(6) . ?
C14 C15 1.391(5) . ?
C14 C45 1.464(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.386(6) . ?
C17 H17 0.9500 . ?
C46 H46 0.9500 . ?
N13 HN13 0.876(19) . ?
N13 H1 0.854(19) . ?
N13 C18 1.339(5) . ?
N14 C19 1.417(5) . ?
N14 C22 1.396(5) . ?
N14 C23 1.348(5) . ?
N15 HN15 0.864(19) . ?
N15 C20 1.328(6) . ?
N15 C21 1.391(6) . ?
N16 C18 1.347(5) . ?
N16 C23 1.345(5) . ?
N17 C24 1.342(5) . ?
N17 C27 1.334(5) . ?
N18 C25 1.339(5) . ?
N18 C26 1.338(5) . ?
C18 C19 1.426(6) . ?
C19 C20 1.364(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9500 . ?
C21 C22 1.328(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.460(5) . ?
C24 C25 1.394(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.387(6) . ?
C27 H27 0.9500 . ?
N19 HN19 0.840(19) . ?
N19 H2 0.844(19) . ?
N19 C28 1.330(5) . ?
N20 C29 1.424(4) . ?
N20 C32 1.398(5) . ?
N20 C33 1.349(5) . ?
N21 HN21 0.859(19) . ?
N21 C30 1.329(5) . ?
N21 C31 1.389(5) . ?
N22 C28 1.354(4) . ?
N22 C33 1.349(5) . ?
N23 C34 1.346(5) . ?
N23 C37 1.332(5) . ?
N24 C35 1.340(5) . ?
N24 C36 1.334(5) . ?
C28 C29 1.428(5) . ?
C29 C30 1.366(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.338(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.457(5) . ?
C34 C35 1.388(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.385(6) . ?
C37 H37 0.9500 . ?
N25 C38 1.120(5) . ?
C38 C39 1.467(5) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N26 C40 1.134(6) . ?
C40 C41 1.453(6) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
N27 C42 1.128(5) . ?
C42 C43 1.471(6) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 I2 I3 178.989(11) . . ?
I6 I5 I4 178.036(12) . . ?
I9 I8 I7 175.952(13) . . ?
I12 I11 I10 178.090(12) . . ?
HN1B N1 HN1A 119(5) . . ?
C1 N1 HN1B 119(3) . . ?
C1 N1 HN1A 122(3) . . ?
C5 N2 C2 106.9(3) . . ?
C5 N2 C44 134.5(3) . . ?
C44 N2 C2 118.6(3) . . ?
C3 N3 HN3 112(4) . . ?
C3 N3 C4 121.1(3) . . ?
C4 N3 HN3 127(4) . . ?
C1 N4 C5 106.8(3) . . ?
C9 N5 C6 115.6(3) . . ?
C7 N6 C8 116.3(3) . . ?
N1 C1 N4 122.0(4) . . ?
N1 C1 C2 128.1(3) . . ?
N4 C1 C2 109.8(3) . . ?
N2 C2 C1 104.3(3) . . ?
C3 C2 N2 119.7(3) . . ?
C3 C2 C1 135.9(3) . . ?
N3 C3 C2 120.1(3) . . ?
N3 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
N3 C4 H4 119.3 . . ?
C44 C4 N3 121.4(4) . . ?
C44 C4 H4 119.3 . . ?
N2 C5 N4 112.1(3) . . ?
N2 C5 C6 125.6(3) . . ?
N4 C5 C6 122.3(3) . . ?
N5 C6 C5 117.6(3) . . ?
N5 C6 C7 122.3(3) . . ?
C7 C6 C5 120.1(3) . . ?
N6 C7 C6 121.4(3) . . ?
N6 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N6 C8 H8 119.0 . . ?
N6 C8 C9 122.1(3) . . ?
C9 C8 H8 119.0 . . ?
N5 C9 C8 122.4(3) . . ?
N5 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
N2 C44 H44 120.4 . . ?
C4 C44 N2 119.2(3) . . ?
C4 C44 H44 120.4 . . ?
HN7B N7 HN7A 116(4) . . ?
C10 N7 HN7B 125(3) . . ?
C10 N7 HN7A 119(3) . . ?
C45 N8 C11 106.2(3) . . ?
C45 N8 C46 135.2(3) . . ?
C46 N8 C11 118.5(3) . . ?
C12 N9 HN9 117(4) . . ?
C12 N9 C13 121.0(3) . . ?
C13 N9 HN9 122(4) . . ?
C45 N10 C10 106.9(3) . . ?
C14 N11 C17 115.9(3) . . ?
C16 N12 C15 116.9(4) . . ?
N7 C10 N10 122.6(4) . . ?
N7 C10 C11 127.8(4) . . ?
N10 C10 C11 109.6(3) . . ?
C10 C11 N8 104.7(3) . . ?
C12 C11 N8 120.3(4) . . ?
C12 C11 C10 135.0(4) . . ?
N9 C12 C11 119.7(4) . . ?
N9 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N9 C13 H13 119.2 . . ?
C46 C13 N9 121.5(4) . . ?
C46 C13 H13 119.2 . . ?
N11 C14 C15 122.1(4) . . ?
N11 C14 C45 118.2(3) . . ?
C15 C14 C45 119.6(3) . . ?
N12 C15 C14 121.4(4) . . ?
N12 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
N12 C16 H16 119.3 . . ?
N12 C16 C17 121.3(4) . . ?
C17 C16 H16 119.3 . . ?
N11 C17 C16 122.4(4) . . ?
N11 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
N8 C45 C14 124.4(3) . . ?
N10 C45 N8 112.6(3) . . ?
N10 C45 C14 123.0(3) . . ?
N8 C46 H46 120.5 . . ?
C13 C46 N8 118.9(4) . . ?
C13 C46 H46 120.5 . . ?
HN13 N13 H1 120(5) . . ?
C18 N13 HN13 118(3) . . ?
C18 N13 H1 118(4) . . ?
C22 N14 C19 118.8(3) . . ?
C23 N14 C19 106.7(3) . . ?
C23 N14 C22 134.5(3) . . ?
C20 N15 HN15 116(4) . . ?
C20 N15 C21 121.2(4) . . ?
C21 N15 HN15 122(4) . . ?
C23 N16 C18 106.9(3) . . ?
C27 N17 C24 116.2(3) . . ?
C26 N18 C25 116.7(3) . . ?
N13 C18 N16 122.2(4) . . ?
N13 C18 C19 128.1(4) . . ?
N16 C18 C19 109.7(3) . . ?
N14 C19 C18 104.5(3) . . ?
C20 C19 N14 120.1(4) . . ?
C20 C19 C18 135.4(4) . . ?
N15 C20 C19 119.5(4) . . ?
N15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
N15 C21 H21A 119.2 . . ?
C22 C21 N15 121.5(4) . . ?
C22 C21 H21A 119.2 . . ?
N14 C22 H22 120.5 . . ?
C21 C22 N14 118.9(4) . . ?
C21 C22 H22 120.5 . . ?
N14 C23 C24 125.0(3) . . ?
N16 C23 N14 112.2(3) . . ?
N16 C23 C24 122.7(3) . . ?
N17 C24 C23 118.4(3) . . ?
N17 C24 C25 121.8(3) . . ?
C25 C24 C23 119.7(3) . . ?
N18 C25 C24 121.4(4) . . ?
N18 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
N18 C26 H26 119.2 . . ?
N18 C26 C27 121.6(4) . . ?
C27 C26 H26 119.2 . . ?
N17 C27 C26 122.2(4) . . ?
N17 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
HN19 N19 H2 118(4) . . ?
C28 N19 HN19 121(3) . . ?
C28 N19 H2 121(3) . . ?
C32 N20 C29 118.7(3) . . ?
C33 N20 C29 106.6(3) . . ?
C33 N20 C32 134.8(3) . . ?
C30 N21 HN21 120(4) . . ?
C30 N21 C31 120.9(3) . . ?
C31 N21 HN21 119(4) . . ?
C33 N22 C28 107.0(3) . . ?
C37 N23 C34 116.3(3) . . ?
C36 N24 C35 116.7(3) . . ?
N19 C28 N22 122.8(3) . . ?
N19 C28 C29 127.8(3) . . ?
N22 C28 C29 109.4(3) . . ?
N20 C29 C28 104.7(3) . . ?
C30 C29 N20 119.6(3) . . ?
C30 C29 C28 135.7(3) . . ?
N21 C30 C29 120.3(3) . . ?
N21 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
N21 C31 H31 119.3 . . ?
C32 C31 N21 121.4(3) . . ?
C32 C31 H31 119.3 . . ?
N20 C32 H32 120.5 . . ?
C31 C32 N20 119.1(3) . . ?
C31 C32 H32 120.5 . . ?
N20 C33 C34 125.3(3) . . ?
N22 C33 N20 112.3(3) . . ?
N22 C33 C34 122.4(3) . . ?
N23 C34 C33 118.0(3) . . ?
N23 C34 C35 121.6(3) . . ?
C35 C34 C33 120.4(3) . . ?
N24 C35 C34 121.5(3) . . ?
N24 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
N24 C36 H36 119.1 . . ?
N24 C36 C37 121.7(3) . . ?
C37 C36 H36 119.1 . . ?
N23 C37 C36 122.1(4) . . ?
N23 C37 H37 118.9 . . ?
C36 C37 H37 118.9 . . ?
N25 C38 C39 179.5(6) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N26 C40 C41 179.1(5) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N27 C42 C43 178.9(5) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -178.0(4) . . . . ?
N1 C1 C2 C3 -0.4(7) . . . . ?
N2 C2 C3 N3 -0.1(5) . . . . ?
N2 C5 C6 N5 -2.0(5) . . . . ?
N2 C5 C6 C7 178.8(3) . . . . ?
N3 C4 C44 N2 0.7(6) . . . . ?
N4 C1 C2 N2 0.1(4) . . . . ?
N4 C1 C2 C3 177.7(4) . . . . ?
N4 C5 C6 N5 175.3(3) . . . . ?
N4 C5 C6 C7 -3.9(5) . . . . ?
N5 C6 C7 N6 -0.9(6) . . . . ?
N6 C8 C9 N5 0.4(6) . . . . ?
C1 N4 C5 N2 0.4(4) . . . . ?
C1 N4 C5 C6 -177.2(3) . . . . ?
C1 C2 C3 N3 -177.4(4) . . . . ?
C2 N2 C5 N4 -0.3(4) . . . . ?
C2 N2 C5 C6 177.2(3) . . . . ?
C2 N2 C44 C4 -1.9(5) . . . . ?
C3 N3 C4 C44 0.8(6) . . . . ?
C4 N3 C3 C2 -1.1(5) . . . . ?
C5 N2 C2 C1 0.1(4) . . . . ?
C5 N2 C2 C3 -178.0(3) . . . . ?
C5 N2 C44 C4 177.5(4) . . . . ?
C5 N4 C1 N1 178.0(3) . . . . ?
C5 N4 C1 C2 -0.3(4) . . . . ?
C5 C6 C7 N6 178.3(3) . . . . ?
C6 N5 C9 C8 -0.7(5) . . . . ?
C7 N6 C8 C9 -0.3(5) . . . . ?
C8 N6 C7 C6 0.5(5) . . . . ?
C9 N5 C6 C5 -178.3(3) . . . . ?
C9 N5 C6 C7 0.9(5) . . . . ?
C44 N2 C2 C1 179.7(3) . . . . ?
C44 N2 C2 C3 1.6(5) . . . . ?
C44 N2 C5 N4 -179.8(4) . . . . ?
C44 N2 C5 C6 -2.3(6) . . . . ?
N7 C10 C11 N8 -178.1(4) . . . . ?
N7 C10 C11 C12 0.4(7) . . . . ?
N8 C11 C12 N9 0.2(6) . . . . ?
N9 C13 C46 N8 0.3(6) . . . . ?
N10 C10 C11 N8 -1.0(4) . . . . ?
N10 C10 C11 C12 177.5(4) . . . . ?
N11 C14 C15 N12 -1.9(6) . . . . ?
N11 C14 C45 N8 5.5(5) . . . . ?
N11 C14 C45 N10 -175.8(3) . . . . ?
N12 C16 C17 N11 -0.8(6) . . . . ?
C10 N10 C45 N8 -0.4(4) . . . . ?
C10 N10 C45 C14 -179.2(3) . . . . ?
C10 C11 C12 N9 -178.2(4) . . . . ?
C11 N8 C45 N10 -0.3(4) . . . . ?
C11 N8 C45 C14 178.5(3) . . . . ?
C11 N8 C46 C13 0.1(5) . . . . ?
C12 N9 C13 C46 -0.5(6) . . . . ?
C13 N9 C12 C11 0.3(6) . . . . ?
C14 N11 C17 C16 -0.6(6) . . . . ?
C15 N12 C16 C17 0.8(6) . . . . ?
C15 C14 C45 N8 -174.9(4) . . . . ?
C15 C14 C45 N10 3.7(6) . . . . ?
C16 N12 C15 C14 0.5(6) . . . . ?
C17 N11 C14 C15 1.9(5) . . . . ?
C17 N11 C14 C45 -178.6(3) . . . . ?
C45 N8 C11 C10 0.8(4) . . . . ?
C45 N8 C11 C12 -178.0(3) . . . . ?
C45 N8 C46 C13 176.9(4) . . . . ?
C45 N10 C10 N7 178.1(4) . . . . ?
C45 N10 C10 C11 0.9(4) . . . . ?
C45 C14 C15 N12 178.6(3) . . . . ?
C46 N8 C11 C10 178.4(3) . . . . ?
C46 N8 C11 C12 -0.3(5) . . . . ?
C46 N8 C45 N10 -177.4(4) . . . . ?
C46 N8 C45 C14 1.4(7) . . . . ?
N13 C18 C19 N14 -179.5(4) . . . . ?
N13 C18 C19 C20 -1.8(7) . . . . ?
N14 C19 C20 N15 -0.6(6) . . . . ?
N14 C23 C24 N17 5.9(5) . . . . ?
N14 C23 C24 C25 -175.0(3) . . . . ?
N15 C21 C22 N14 0.3(6) . . . . ?
N16 C18 C19 N14 -0.1(4) . . . . ?
N16 C18 C19 C20 177.6(4) . . . . ?
N16 C23 C24 N17 -174.8(3) . . . . ?
N16 C23 C24 C25 4.3(5) . . . . ?
N17 C24 C25 N18 -2.3(6) . . . . ?
N18 C26 C27 N17 -2.6(6) . . . . ?
C18 N16 C23 N14 0.7(4) . . . . ?
C18 N16 C23 C24 -178.6(3) . . . . ?
C18 C19 C20 N15 -178.0(4) . . . . ?
C19 N14 C22 C21 0.4(5) . . . . ?
C19 N14 C23 N16 -0.8(4) . . . . ?
C19 N14 C23 C24 178.5(3) . . . . ?
C20 N15 C21 C22 -1.2(6) . . . . ?
C21 N15 C20 C19 1.4(6) . . . . ?
C22 N14 C19 C18 177.8(3) . . . . ?
C22 N14 C19 C20 -0.3(5) . . . . ?
C22 N14 C23 N16 -177.5(4) . . . . ?
C22 N14 C23 C24 1.8(6) . . . . ?
C23 N14 C19 C18 0.5(4) . . . . ?
C23 N14 C19 C20 -177.6(3) . . . . ?
C23 N14 C22 C21 176.9(4) . . . . ?
C23 N16 C18 N13 179.1(4) . . . . ?
C23 N16 C18 C19 -0.4(4) . . . . ?
C23 C24 C25 N18 178.6(3) . . . . ?
C24 N17 C27 C26 0.3(6) . . . . ?
C25 N18 C26 C27 2.4(6) . . . . ?
C26 N18 C25 C24 0.0(6) . . . . ?
C27 N17 C24 C23 -178.8(3) . . . . ?
C27 N17 C24 C25 2.1(5) . . . . ?
N19 C28 C29 N20 179.5(4) . . . . ?
N19 C28 C29 C30 1.6(7) . . . . ?
N20 C29 C30 N21 1.0(5) . . . . ?
N20 C33 C34 N23 1.7(5) . . . . ?
N20 C33 C34 C35 -179.4(3) . . . . ?
N21 C31 C32 N20 -0.4(5) . . . . ?
N22 C28 C29 N20 0.2(4) . . . . ?
N22 C28 C29 C30 -177.7(4) . . . . ?
N22 C33 C34 N23 -176.4(3) . . . . ?
N22 C33 C34 C35 2.5(5) . . . . ?
N23 C34 C35 N24 0.9(6) . . . . ?
N24 C36 C37 N23 -0.2(6) . . . . ?
C28 N22 C33 N20 0.1(4) . . . . ?
C28 N22 C33 C34 178.5(3) . . . . ?
C28 C29 C30 N21 178.7(4) . . . . ?
C29 N20 C32 C31 1.6(5) . . . . ?
C29 N20 C33 N22 0.0(4) . . . . ?
C29 N20 C33 C34 -178.3(3) . . . . ?
C30 N21 C31 C32 -0.5(6) . . . . ?
C31 N21 C30 C29 0.2(5) . . . . ?
C32 N20 C29 C28 179.8(3) . . . . ?
C32 N20 C29 C30 -1.9(5) . . . . ?
C32 N20 C33 N22 -179.8(4) . . . . ?
C32 N20 C33 C34 1.9(6) . . . . ?
C33 N20 C29 C28 -0.1(4) . . . . ?
C33 N20 C29 C30 178.2(3) . . . . ?
C33 N20 C32 C31 -178.6(4) . . . . ?
C33 N22 C28 N19 -179.5(3) . . . . ?
C33 N22 C28 C29 -0.2(4) . . . . ?
C33 C34 C35 N24 -177.9(3) . . . . ?
C34 N23 C37 C36 0.3(5) . . . . ?
C35 N24 C36 C37 0.5(5) . . . . ?
C36 N24 C35 C34 -0.8(5) . . . . ?
C37 N23 C34 C33 178.3(3) . . . . ?
C37 N23 C34 C35 -0.6(5) . . . . ?

_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_p21c_a
_database_code_depnum_ccdc_archive 'CCDC 2182015'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3.333(I3), C20 H16 N12'
_chemical_formula_sum            'C20 H16 I10 N12'
_chemical_formula_weight         1693.45
_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'

_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                   25.1259(13)
_cell_length_b                   7.4309(4)
_cell_length_c                   21.0334(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.923(2)
_cell_angle_gamma                90
_cell_volume                     3827.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9308
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.155
_exptl_absorpt_coefficient_mu    8.128
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.939
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3000
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.017
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56327
_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         28.500
_diffrn_reflns_theta_min         2.288
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8281
_reflns_number_total             9664
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         1.220
_refine_diff_density_min         -1.201
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         9664
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+12.0993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0587
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 HN10-N10
 0.86 with sigma of 0.02
 N10-H1
 0.86 with sigma of 0.02
 HN9-N9
 0.86 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 N7(HN7), C3(H3), C4(H4), C5(H5), C8(H8), C9(H2), C10(H10), C13(H13), C14(H14),
  C15(H15), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.49502(2) 0.68721(4) 0.32147(2) 0.02417(7) Uani 1 1 d . . . . .
I2 I 0.59079(2) 0.62135(4) 0.41933(2) 0.01910(6) Uani 1 1 d . . . . .
I3 I 0.69197(2) 0.53141(4) 0.52210(2) 0.02005(6) Uani 1 1 d . . . . .
I4 I 0.66302(2) 0.58212(4) 0.66089(2) 0.01881(6) Uani 1 1 d . . . . .
I5 I 0.64418(2) 0.63170(5) 0.78376(2) 0.02592(7) Uani 1 1 d . . . . .
I6 I 0.88033(2) 0.34148(4) 0.52556(2) 0.02689(7) Uani 1 1 d . . . . .
I7 I 0.84479(2) 0.41965(4) 0.63853(2) 0.01968(6) Uani 1 1 d . . . . .
I8 I 0.80751(2) 0.49238(4) 0.76777(2) 0.01995(6) Uani 1 1 d . . . . .
I9 I 0.91281(2) 0.37235(4) 0.86062(2) 0.02078(6) Uani 1 1 d . . . . .
I10 I 1.00960(2) 0.24960(5) 0.94319(2) 0.03087(8) Uani 1 1 d . . . . .
N1 N 0.71038(14) 1.0418(5) 0.62709(18) 0.0175(7) Uani 1 1 d . . . . .
N2 N 0.79184(15) 1.0140(5) 0.78773(17) 0.0166(7) Uani 1 1 d . . . . .
N3 N 0.69705(16) 1.1097(5) 0.76322(19) 0.0225(8) Uani 1 1 d . . . . .
N4 N 0.80326(15) 0.9675(5) 0.68954(17) 0.0174(7) Uani 1 1 d . . . . .
N5 N 0.91136(16) 0.8866(6) 0.72598(19) 0.0244(8) Uani 1 1 d . . . . .
N6 N 0.90541(16) 0.8861(5) 0.83872(18) 0.0215(8) Uani 1 1 d . . . . .
N7 N 0.66023(14) 1.0532(5) 0.52221(18) 0.0170(7) Uani 1 1 d . . . . .
HN7 H 0.659483 1.030360 0.480971 0.020 Uiso 1 1 calc R U . . .
N8 N 0.73803(15) 0.9741(5) 0.46657(18) 0.0205(8) Uani 1 1 d . . . . .
N9 N 0.80205(15) 0.9155(5) 0.56608(18) 0.0175(7) Uani 1 1 d D . . . .
HN9 H 0.813(12) 0.92(4) 0.608(2) 0.54(19) Uiso 1 1 d D . . . .
N10 N 0.60565(16) 1.1431(6) 0.59342(19) 0.0215(8) Uani 1 1 d D . . . .
H1 H 0.5753(12) 1.188(6) 0.597(2) 0.016(12) Uiso 1 1 d D . . . .
HN10 H 0.6332(17) 1.125(8) 0.626(2) 0.042(18) Uiso 1 1 d D . . . .
N11 N 0.58058(15) 1.1173(5) 0.41985(18) 0.0192(8) Uani 1 1 d . . . . .
N12 N 0.52232(15) 1.2107(5) 0.49025(18) 0.0211(8) Uani 1 1 d . . . . .
C1 C 0.75009(17) 1.0219(6) 0.6820(2) 0.0165(8) Uani 1 1 d . . . . .
C2 C 0.74172(17) 1.0518(6) 0.7445(2) 0.0170(8) Uani 1 1 d . . . . .
C3 C 0.7020(2) 1.1319(7) 0.8257(2) 0.0267(10) Uani 1 1 d . . . . .
H3 H 0.671162 1.173154 0.840743 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7519(2) 1.0970(7) 0.8731(2) 0.0264(10) Uani 1 1 d . . . . .
H4 H 0.753436 1.115831 0.918184 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7965(2) 1.0378(7) 0.8540(2) 0.0236(10) Uani 1 1 d . . . . .
H5 H 0.829698 1.013409 0.884555 0.028 Uiso 1 1 calc R U . . .
C6 C 0.82880(17) 0.9629(6) 0.7525(2) 0.0162(8) Uani 1 1 d . . . . .
C7 C 0.88543(17) 0.9090(6) 0.7744(2) 0.0188(9) Uani 1 1 d . . . . .
C8 C 0.96384(19) 0.8341(8) 0.7449(3) 0.0297(11) Uani 1 1 d . . . . .
H8 H 0.984332 0.815161 0.712650 0.036 Uiso 1 1 calc R U . . .
C9 C 0.98888(19) 0.8066(7) 0.8096(2) 0.0284(11) Uani 1 1 d . . . . .
H2 H 1.025941 0.769665 0.822196 0.034 Uiso 1 1 calc R U . . .
C10 C 0.95776(19) 0.8352(6) 0.8557(2) 0.0248(10) Uani 1 1 d . . . . .
H10 H 0.974165 0.818168 0.900565 0.030 Uiso 1 1 calc R U . . .
C11 C 0.70998(17) 1.0214(6) 0.5666(2) 0.0173(8) Uani 1 1 d . . . . .
C12 C 0.75322(17) 0.9671(6) 0.5314(2) 0.0160(8) Uani 1 1 d . . . . .
C13 C 0.83819(18) 0.8574(6) 0.5327(2) 0.0214(9) Uani 1 1 d . . . . .
H13 H 0.873121 0.817474 0.555708 0.026 Uiso 1 1 calc R U . . .
C14 C 0.82557(19) 0.8542(6) 0.4650(2) 0.0223(9) Uani 1 1 d . . . . .
H14 H 0.850979 0.811336 0.441159 0.027 Uiso 1 1 calc R U . . .
C15 C 0.77476(19) 0.9157(7) 0.4337(2) 0.0241(10) Uani 1 1 d . . . . .
H15 H 0.765383 0.916961 0.387351 0.029 Uiso 1 1 calc R U . . .
C16 C 0.61373(17) 1.1144(6) 0.5354(2) 0.0169(8) Uani 1 1 d . . . . .
C17 C 0.56880(17) 1.1491(6) 0.4777(2) 0.0191(9) Uani 1 1 d . . . . .
C18 C 0.48267(19) 1.2414(7) 0.4375(2) 0.0249(10) Uani 1 1 d . . . . .
H18 H 0.448705 1.286925 0.443166 0.030 Uiso 1 1 calc R U . . .
C19 C 0.48915(19) 1.2095(6) 0.3752(2) 0.0250(10) Uani 1 1 d . . . . .
H19 H 0.460134 1.229476 0.338276 0.030 Uiso 1 1 calc R U . . .
C20 C 0.53948(19) 1.1474(6) 0.3682(2) 0.0226(9) Uani 1 1 d . . . . .
H20 H 0.545022 1.125438 0.325666 0.027 Uiso 1 1 calc R U . . .


_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
I1 I2 2.8376(4) . ?
I2 I3 3.0206(4) . ?
I4 I5 2.7544(4) . ?
I6 I7 2.7804(4) . ?
I7 I8 3.1140(4) . ?
I8 I9 3.0494(4) . ?
I9 I10 2.8058(4) . ?
N1 C1 1.355(5) . ?
N1 C11 1.279(6) . ?
N2 C2 1.407(5) . ?
N2 C5 1.383(5) . ?
N2 C6 1.364(6) . ?
N3 C2 1.341(6) . ?
N3 C3 1.303(6) . ?
N4 C1 1.370(5) . ?
N4 C6 1.337(5) . ?
N5 C7 1.337(6) . ?
N5 C8 1.347(6) . ?
N6 C7 1.344(6) . ?
N6 C10 1.338(6) . ?
N7 HN7 0.8800 . ?
N7 C11 1.403(5) . ?
N7 C16 1.340(5) . ?
N8 C12 1.332(5) . ?
N8 C15 1.343(6) . ?
N9 HN9 0.86(2) . ?
N9 C12 1.336(5) . ?
N9 C13 1.338(6) . ?
N10 H1 0.853(19) . ?
N10 HN10 0.87(2) . ?
N10 C16 1.298(6) . ?
N11 C17 1.335(6) . ?
N11 C20 1.339(6) . ?
N12 C17 1.335(6) . ?
N12 C18 1.334(6) . ?
C1 C2 1.394(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.442(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.346(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.450(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(7) . ?
C9 H2 0.9500 . ?
C9 C10 1.391(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.501(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.484(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(6) . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 I2 I3 177.141(14) . . ?
I6 I7 I8 177.547(14) . . ?
I9 I8 I7 96.953(11) . . ?
I10 I9 I8 177.767(15) . . ?
C11 N1 C1 132.5(4) . . ?
C5 N2 C2 119.2(4) . . ?
C6 N2 C2 108.9(3) . . ?
C6 N2 C5 131.9(4) . . ?
C3 N3 C2 116.1(4) . . ?
C6 N4 C1 111.2(4) . . ?
C7 N5 C8 115.0(4) . . ?
C10 N6 C7 115.4(4) . . ?
C11 N7 HN7 116.3 . . ?
C16 N7 HN7 116.3 . . ?
C16 N7 C11 127.4(4) . . ?
C12 N8 C15 116.2(4) . . ?
C12 N9 HN9 126(10) . . ?
C12 N9 C13 117.0(4) . . ?
C13 N9 HN9 117(10) . . ?
H1 N10 HN10 124(5) . . ?
C16 N10 H1 119(3) . . ?
C16 N10 HN10 117(4) . . ?
C17 N11 C20 114.9(4) . . ?
C18 N12 C17 114.7(4) . . ?
N1 C1 N4 130.0(4) . . ?
N1 C1 C2 123.3(4) . . ?
N4 C1 C2 106.7(4) . . ?
N3 C2 N2 124.1(4) . . ?
N3 C2 C1 129.9(4) . . ?
C1 C2 N2 106.0(4) . . ?
N3 C3 H3 118.4 . . ?
N3 C3 C4 123.1(4) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
N2 C5 H5 121.5 . . ?
C4 C5 N2 117.1(4) . . ?
C4 C5 H5 121.5 . . ?
N2 C6 C7 130.0(4) . . ?
N4 C6 N2 107.2(4) . . ?
N4 C6 C7 122.7(4) . . ?
N5 C7 N6 127.9(4) . . ?
N5 C7 C6 113.8(4) . . ?
N6 C7 C6 118.3(4) . . ?
N5 C8 H8 118.8 . . ?
N5 C8 C9 122.3(5) . . ?
C9 C8 H8 118.8 . . ?
C8 C9 H2 121.3 . . ?
C8 C9 C10 117.4(4) . . ?
C10 C9 H2 121.3 . . ?
N6 C10 C9 122.0(4) . . ?
N6 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N1 C11 N7 116.7(4) . . ?
N1 C11 C12 132.6(4) . . ?
N7 C11 C12 110.6(4) . . ?
N8 C12 N9 126.0(4) . . ?
N8 C12 C11 114.9(4) . . ?
N9 C12 C11 119.0(4) . . ?
N9 C13 H13 119.4 . . ?
N9 C13 C14 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.3(4) . . ?
C15 C14 H14 121.3 . . ?
N8 C15 C14 122.1(4) . . ?
N8 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
N7 C16 C17 115.3(4) . . ?
N10 C16 N7 125.3(4) . . ?
N10 C16 C17 119.4(4) . . ?
N11 C17 C16 115.6(4) . . ?
N12 C17 N11 128.5(4) . . ?
N12 C17 C16 115.9(4) . . ?
N12 C18 H18 118.8 . . ?
N12 C18 C19 122.5(4) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 H19 121.2 . . ?
C18 C19 C20 117.6(4) . . ?
C20 C19 H19 121.2 . . ?
N11 C20 C19 121.8(4) . . ?
N11 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 178.9(4) . . . . ?
N1 C1 C2 N3 -3.0(8) . . . . ?
N1 C11 C12 N8 -175.1(5) . . . . ?
N1 C11 C12 N9 5.6(7) . . . . ?
N2 C6 C7 N5 -173.0(4) . . . . ?
N2 C6 C7 N6 7.6(7) . . . . ?
N3 C3 C4 C5 -0.2(8) . . . . ?
N4 C1 C2 N2 0.4(5) . . . . ?
N4 C1 C2 N3 178.5(4) . . . . ?
N4 C6 C7 N5 8.0(6) . . . . ?
N4 C6 C7 N6 -171.4(4) . . . . ?
N5 C8 C9 C10 0.1(8) . . . . ?
N7 C11 C12 N8 5.3(5) . . . . ?
N7 C11 C12 N9 -174.0(4) . . . . ?
N7 C16 C17 N11 -0.9(6) . . . . ?
N7 C16 C17 N12 -179.8(4) . . . . ?
N9 C13 C14 C15 0.9(7) . . . . ?
N10 C16 C17 N11 179.6(4) . . . . ?
N10 C16 C17 N12 0.7(6) . . . . ?
N12 C18 C19 C20 -1.5(7) . . . . ?
C1 N1 C11 N7 179.5(4) . . . . ?
C1 N1 C11 C12 0.0(8) . . . . ?
C1 N4 C6 N2 0.4(5) . . . . ?
C1 N4 C6 C7 179.6(4) . . . . ?
C2 N2 C5 C4 -0.1(6) . . . . ?
C2 N2 C6 N4 -0.1(5) . . . . ?
C2 N2 C6 C7 -179.3(4) . . . . ?
C2 N3 C3 C4 -0.2(7) . . . . ?
C3 N3 C2 N2 0.5(7) . . . . ?
C3 N3 C2 C1 -177.3(5) . . . . ?
C3 C4 C5 N2 0.4(7) . . . . ?
C5 N2 C2 N3 -0.3(6) . . . . ?
C5 N2 C2 C1 177.9(4) . . . . ?
C5 N2 C6 N4 -177.9(4) . . . . ?
C5 N2 C6 C7 3.0(8) . . . . ?
C6 N2 C2 N3 -178.4(4) . . . . ?
C6 N2 C2 C1 -0.2(5) . . . . ?
C6 N2 C5 C4 177.4(5) . . . . ?
C6 N4 C1 N1 -178.9(4) . . . . ?
C6 N4 C1 C2 -0.5(5) . . . . ?
C7 N5 C8 C9 -0.4(8) . . . . ?
C7 N6 C10 C9 -0.6(7) . . . . ?
C8 N5 C7 N6 0.2(7) . . . . ?
C8 N5 C7 C6 -179.1(4) . . . . ?
C8 C9 C10 N6 0.5(8) . . . . ?
C10 N6 C7 N5 0.3(7) . . . . ?
C10 N6 C7 C6 179.6(4) . . . . ?
C11 N1 C1 N4 -1.9(8) . . . . ?
C11 N1 C1 C2 179.9(5) . . . . ?
C11 N7 C16 N10 -5.3(7) . . . . ?
C11 N7 C16 C17 175.2(4) . . . . ?
C12 N8 C15 C14 -0.8(7) . . . . ?
C12 N9 C13 C14 1.1(6) . . . . ?
C13 N9 C12 N8 -3.4(7) . . . . ?
C13 N9 C12 C11 175.8(4) . . . . ?
C13 C14 C15 N8 -1.1(7) . . . . ?
C15 N8 C12 N9 3.2(7) . . . . ?
C15 N8 C12 C11 -176.1(4) . . . . ?
C16 N7 C11 N1 4.9(6) . . . . ?
C16 N7 C11 C12 -175.5(4) . . . . ?
C17 N11 C20 C19 1.0(7) . . . . ?
C17 N12 C18 C19 0.8(7) . . . . ?
C18 N12 C17 N11 1.0(7) . . . . ?
C18 N12 C17 C16 179.8(4) . . . . ?
C18 C19 C20 N11 0.5(7) . . . . ?
C20 N11 C17 N12 -1.9(7) . . . . ?
C20 N11 C17 C16 179.3(4) . . . . ?

_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_mo_d8_5538_11oct21_ajp6_0m
_database_code_depnum_ccdc_archive 'CCDC 2182013'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi4 I16, 4(C H4 O), 4(C10 H9 N6)'
_chemical_formula_sum            'C44 H52 Bi4 I16 N24 O4'
_chemical_formula_weight         3847.41
_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      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                   13.1812(4)
_cell_length_b                   13.8011(4)
_cell_length_c                   14.1644(5)
_cell_angle_alpha                108.4490(10)
_cell_angle_beta                 99.637(2)
_cell_angle_gamma                115.4060(10)
_cell_volume                     2065.08(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.397
_shelx_estimated_absorpt_T_min   0.150
_exptl_absorpt_coefficient_mu    14.528
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.094
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            59364
_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         27.499
_diffrn_reflns_theta_min         2.319
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8369
_reflns_number_total             9485
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         2.163
_refine_diff_density_min         -1.896
_refine_diff_density_rms         0.235
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         9485
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.241
_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)+20.8472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0683
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 HN10-N10
 0.86 with sigma of 0.02
 HN4-N4
 0.86 with sigma of 0.02
 HN7A-N7
 0.86 with sigma of 0.02
 HN1A-N1
 0.86 with sigma of 0.02
 HN1B-N1
 0.86 with sigma of 0.02
 N7-HN7B
 0.86 with sigma of 0.02
 H1O1-O1
 0.85 with sigma of 0.02
 H1O2-O2
 0.85 with sigma of 0.02
 C1-HN10 \\sim C6-HN10
 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C3(H3), C4(H4A),
 C5(H5), C8(H8), C9(H9), C10(H10A)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 0.60352(2) 0.20056(2) 0.34097(2) 0.01849(6) Uani 1 1 d . . . . .
Bi2 Bi 0.36275(2) 0.06301(2) 0.53600(2) 0.01758(6) Uani 1 1 d . . . . .
I1 I 0.55396(5) 0.17512(4) 0.12321(4) 0.02472(10) Uani 1 1 d . . . . .
I2 I 0.86086(5) 0.33958(5) 0.39512(4) 0.03041(11) Uani 1 1 d . . . . .
I3 I 0.57961(5) 0.40857(4) 0.43531(4) 0.02457(10) Uani 1 1 d . . . . .
I4 I 0.65376(4) 0.18975(4) 0.57154(3) 0.01885(9) Uani 1 1 d . . . . .
I5 I 0.30949(4) 0.04746(4) 0.31021(3) 0.02116(9) Uani 1 1 d . . . . .
I6 I 0.11164(4) -0.05686(5) 0.50911(4) 0.02864(11) Uani 1 1 d . . . . .
I7 I 0.43288(4) 0.06828(4) 0.75721(3) 0.02001(9) Uani 1 1 d . . . . .
I8 I 0.41030(5) 0.30829(4) 0.63400(4) 0.02369(10) Uani 1 1 d . . . . .
O1 O 0.7564(5) 0.7124(5) 0.6528(4) 0.0280(11) Uani 1 1 d D . . . .
H1O1 H 0.691(8) 0.708(16) 0.627(13) 0.15(7) Uiso 1 1 d D . . . .
C21 C 0.8418(7) 0.7479(8) 0.6031(7) 0.0339(18) Uani 1 1 d . . . . .
H21A H 0.801760 0.703885 0.525642 0.051 Uiso 1 1 calc R U . . .
H21B H 0.904230 0.730718 0.625478 0.051 Uiso 1 1 calc R U . . .
H21C H 0.878543 0.833577 0.623832 0.051 Uiso 1 1 calc R U . . .
O2 O 0.7529(5) 0.4978(5) 0.7535(5) 0.0325(12) Uani 1 1 d D . . . .
H1O2 H 0.679(3) 0.448(6) 0.715(6) 0.039 Uiso 1 1 d D U . . .
C22 C 0.8430(8) 0.5244(8) 0.7039(6) 0.0329(18) Uani 1 1 d . . . . .
H22A H 0.806735 0.512841 0.632037 0.049 Uiso 1 1 calc R U . . .
H22B H 0.874344 0.470927 0.699929 0.049 Uiso 1 1 calc R U . . .
H22C H 0.908777 0.607217 0.746384 0.049 Uiso 1 1 calc R U . . .
N1 N 0.5826(6) 0.6301(6) 0.8234(6) 0.0278(14) Uani 1 1 d D . . . .
HN1A H 0.570(12) 0.638(12) 0.765(6) 0.09(5) Uiso 1 1 d D . . . .
HN1B H 0.528(9) 0.615(12) 0.852(10) 0.10(5) Uiso 1 1 d D . . . .
N2 N 0.8681(6) 0.8171(5) 1.0313(5) 0.0215(12) Uani 1 1 d . . . . .
N3 N 0.6851(6) 0.7308(6) 1.0691(5) 0.0268(14) Uani 1 1 d . . . . .
N4 N 0.7931(6) 0.7509(5) 0.8596(5) 0.0220(12) Uani 1 1 d D . . . .
HN4 H 0.794(9) 0.743(9) 0.797(4) 0.05(3) Uiso 1 1 d D . . . .
N5 N 1.0164(6) 0.8576(6) 0.8390(5) 0.0271(14) Uani 1 1 d . . . . .
N6 N 1.1092(6) 0.9399(6) 1.0288(5) 0.0284(14) Uani 1 1 d . . . . .
C11 C 0.6955(7) 0.7050(6) 0.8892(6) 0.0230(15) Uani 1 1 d . . . . .
C12 C 0.7434(7) 0.7483(6) 1.0011(6) 0.0221(14) Uani 1 1 d . . . . .
C13 C 0.7522(8) 0.7807(7) 1.1683(6) 0.0289(17) Uani 1 1 d . . . . .
H13 H 0.713996 0.770705 1.218550 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8801(8) 0.8496(7) 1.2064(6) 0.0325(18) Uani 1 1 d . . . . .
H14 H 0.924386 0.883090 1.280025 0.039 Uiso 1 1 calc R U . . .
C15 C 0.9388(7) 0.8675(7) 1.1380(6) 0.0256(15) Uani 1 1 d . . . . .
H15 H 1.024032 0.912292 1.161648 0.031 Uiso 1 1 calc R U . . .
C16 C 0.8980(7) 0.8188(6) 0.9442(6) 0.0250(15) Uani 1 1 d . . . . .
C17 C 1.0153(7) 0.8751(6) 0.9376(6) 0.0249(15) Uani 1 1 d . . . . .
C18 C 1.1257(7) 0.9085(7) 0.8327(6) 0.0265(16) Uani 1 1 d . . . . .
H18 H 1.131629 0.898130 0.764629 0.032 Uiso 1 1 calc R U . . .
C19 C 1.2300(7) 0.9753(7) 0.9204(6) 0.0266(16) Uani 1 1 d . . . . .
H19 H 1.306728 1.010597 0.914031 0.032 Uiso 1 1 calc R U . . .
C20 C 1.2178(7) 0.9886(7) 1.0186(6) 0.0296(17) Uani 1 1 d . . . . .
H20 H 1.287987 1.033402 1.080560 0.036 Uiso 1 1 calc R U . . .
N7 N 0.5733(7) 0.4218(7) 0.9206(6) 0.0354(16) Uani 1 1 d D . . . .
HN7A H 0.564(10) 0.394(9) 0.854(3) 0.05(3) Uiso 1 1 d D . . . .
HN7B H 0.526(8) 0.390(9) 0.952(8) 0.064 Uiso 1 1 d D U . . .
N8 N 0.8621(6) 0.5724(5) 1.1258(5) 0.0250(13) Uani 1 1 d . . . . .
N9 N 0.6748(6) 0.4875(6) 1.1588(6) 0.0307(15) Uani 1 1 d . . . . .
N10 N 0.7880(6) 0.5232(5) 0.9558(5) 0.0236(13) Uani 1 1 d D . . . .
HN10 H 0.7848(18) 0.514(7) 0.891(2) 0.05(3) Uiso 1 1 d D . . . .
N11 N 1.0128(6) 0.6309(6) 0.9402(5) 0.0309(15) Uani 1 1 d . . . . .
N12 N 1.1029(6) 0.6841(6) 1.1261(6) 0.0313(15) Uani 1 1 d . . . . .
C1 C 0.6899(7) 0.4787(7) 0.9852(6) 0.0286(16) Uani 1 1 d D . . . .
C2 C 0.7345(7) 0.5098(6) 1.0938(6) 0.0267(16) Uani 1 1 d . . . . .
C3 C 0.7428(8) 0.5273(7) 1.2576(7) 0.0308(17) Uani 1 1 d . . . . .
H3 H 0.703022 0.511521 1.305713 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8691(9) 0.5911(8) 1.2982(7) 0.036(2) Uani 1 1 d . . . . .
H4A H 0.911738 0.617994 1.371028 0.044 Uiso 1 1 calc R U . . .
C5 C 0.9303(8) 0.6142(7) 1.2295(7) 0.0331(18) Uani 1 1 d . . . . .
H5 H 1.015554 0.656878 1.253401 0.040 Uiso 1 1 calc R U . . .
C6 C 0.8922(7) 0.5794(6) 1.0405(6) 0.0221(14) Uani 1 1 d D . . . .
C7 C 1.0110(7) 0.6354(6) 1.0350(6) 0.0224(14) Uani 1 1 d . . . . .
C8 C 1.1270(7) 0.6831(7) 0.9373(7) 0.0307(17) Uani 1 1 d . . . . .
H8 H 1.136988 0.681195 0.871938 0.037 Uiso 1 1 calc R U . . .
C9 C 1.2260(8) 0.7374(7) 1.0258(7) 0.0299(17) Uani 1 1 d . . . . .
H9 H 1.303768 0.775530 1.022254 0.036 Uiso 1 1 calc R U . . .
C10 C 1.2139(8) 0.7373(7) 1.1213(7) 0.0328(18) Uani 1 1 d . . . . .
H10A H 1.283012 0.774298 1.182775 0.039 Uiso 1 1 calc R U . . .


_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 2.9166(5) . ?
Bi1 I2 2.8963(6) . ?
Bi1 I3 2.9353(5) . ?
Bi1 I4 3.2857(5) . ?
Bi1 I5 3.3912(5) . ?
Bi1 I7 3.3037(5) 2_656 ?
Bi2 I4 3.3265(5) . ?
Bi2 I4 3.2266(5) 2_656 ?
Bi2 I5 3.0744(5) . ?
Bi2 I6 2.8842(6) . ?
Bi2 I7 3.0831(5) . ?
Bi2 I8 2.9483(5) . ?
O1 H1O1 0.85(2) . ?
O1 C21 1.419(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O2 H1O2 0.85(2) . ?
O2 C22 1.451(9) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 HN1A 0.86(2) . ?
N1 HN1B 0.86(2) . ?
N1 C11 1.326(10) . ?
N2 C12 1.398(10) . ?
N2 C15 1.394(9) . ?
N2 C16 1.361(9) . ?
N3 C12 1.347(9) . ?
N3 C13 1.297(10) . ?
N4 HN4 0.86(2) . ?
N4 C11 1.372(9) . ?
N4 C16 1.360(10) . ?
N5 C17 1.343(9) . ?
N5 C18 1.338(10) . ?
N6 C17 1.335(10) . ?
N6 C20 1.351(10) . ?
C11 C12 1.417(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.426(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.355(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.438(11) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(10) . ?
C20 H20 0.9500 . ?
N7 HN7A 0.87(2) . ?
N7 HN7B 0.87(2) . ?
N7 C1 1.361(11) . ?
N8 C2 1.425(10) . ?
N8 C5 1.369(11) . ?
N8 C6 1.352(9) . ?
N9 C2 1.332(10) . ?
N9 C3 1.317(11) . ?
N10 HN10 0.87(2) . ?
N10 C1 1.373(9) . ?
N10 C6 1.369(10) . ?
N11 C7 1.330(9) . ?
N11 C8 1.376(10) . ?
N12 C7 1.346(10) . ?
N12 C10 1.352(11) . ?
C1 C2 1.400(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(13) . ?
C4 H4A 0.9500 . ?
C4 C5 1.393(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.448(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.363(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(11) . ?
C10 H10A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Bi1 I3 98.278(15) . . ?
I1 Bi1 I4 171.554(15) . . ?
I1 Bi1 I5 94.161(14) . . ?
I1 Bi1 I7 86.327(13) . 2_656 ?
I2 Bi1 I1 92.804(16) . . ?
I2 Bi1 I3 94.595(16) . . ?
I2 Bi1 I4 88.493(15) . . ?
I2 Bi1 I5 172.912(16) . . ?
I2 Bi1 I7 98.546(15) . 2_656 ?
I3 Bi1 I4 89.930(13) . . ?
I3 Bi1 I5 83.108(14) . . ?
I3 Bi1 I7 165.855(15) . 2_656 ?
I4 Bi1 I5 84.808(12) . . ?
I4 Bi1 I7 85.227(12) . 2_656 ?
I7 Bi1 I5 83.224(12) 2_656 . ?
I4 Bi2 I4 86.815(13) 2_656 . ?
I5 Bi2 I4 85.531(13) . 2_656 ?
I5 Bi2 I4 89.332(13) . . ?
I5 Bi2 I7 174.118(15) . . ?
I6 Bi2 I4 176.629(15) . . ?
I6 Bi2 I4 90.692(15) . 2_656 ?
I6 Bi2 I5 92.738(16) . . ?
I6 Bi2 I7 91.092(15) . . ?
I6 Bi2 I8 96.805(16) . . ?
I7 Bi2 I4 89.963(13) . 2_656 ?
I7 Bi2 I4 86.641(13) . . ?
I8 Bi2 I4 172.454(15) . 2_656 ?
I8 Bi2 I4 85.728(14) . . ?
I8 Bi2 I5 93.224(14) . . ?
I8 Bi2 I7 90.752(14) . . ?
Bi1 I4 Bi2 91.391(13) . . ?
Bi2 I4 Bi1 91.080(12) 2_656 . ?
Bi2 I4 Bi2 93.186(13) 2_656 . ?
Bi2 I5 Bi1 93.959(14) . . ?
Bi2 I7 Bi1 93.341(13) . 2_656 ?
C21 O1 H1O1 116(10) . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 O2 H1O2 120(6) . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
HN1A N1 HN1B 120(10) . . ?
C11 N1 HN1A 112(10) . . ?
C11 N1 HN1B 117(10) . . ?
C15 N2 C12 118.8(6) . . ?
C16 N2 C12 109.7(6) . . ?
C16 N2 C15 131.4(7) . . ?
C13 N3 C12 115.8(7) . . ?
C11 N4 HN4 128(7) . . ?
C16 N4 HN4 120(7) . . ?
C16 N4 C11 112.0(6) . . ?
C18 N5 C17 115.0(7) . . ?
C17 N6 C20 115.1(6) . . ?
N1 C11 N4 125.6(7) . . ?
N1 C11 C12 129.1(7) . . ?
N4 C11 C12 105.2(6) . . ?
N2 C12 C11 106.6(6) . . ?
N3 C12 N2 124.4(7) . . ?
N3 C12 C11 128.9(7) . . ?
N3 C13 H13 118.1 . . ?
N3 C13 C14 123.8(7) . . ?
C14 C13 H13 118.1 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(8) . . ?
C15 C14 H14 119.8 . . ?
N2 C15 H15 121.6 . . ?
C14 C15 N2 116.7(8) . . ?
C14 C15 H15 121.6 . . ?
N2 C16 C17 128.8(7) . . ?
N4 C16 N2 106.4(7) . . ?
N4 C16 C17 124.8(7) . . ?
N5 C17 C16 115.1(7) . . ?
N6 C17 N5 127.8(7) . . ?
N6 C17 C16 117.1(7) . . ?
N5 C18 H18 118.5 . . ?
N5 C18 C19 123.0(7) . . ?
C19 C18 H18 118.5 . . ?
C18 C19 H19 121.6 . . ?
C18 C19 C20 116.9(7) . . ?
C20 C19 H19 121.6 . . ?
N6 C20 C19 122.1(8) . . ?
N6 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
HN7A N7 HN7B 128(10) . . ?
C1 N7 HN7A 113(7) . . ?
C1 N7 HN7B 110(8) . . ?
C5 N8 C2 119.5(7) . . ?
C6 N8 C2 108.6(6) . . ?
C6 N8 C5 131.9(7) . . ?
C3 N9 C2 114.9(7) . . ?
C1 N10 HN10 124.9(15) . . ?
C6 N10 HN10 124.3(15) . . ?
C6 N10 C1 110.7(6) . . ?
C7 N11 C8 113.3(7) . . ?
C7 N12 C10 115.6(7) . . ?
N7 C1 N10 125.4(7) . . ?
N7 C1 C2 128.1(7) . . ?
N10 C1 C2 106.5(7) . . ?
N9 C2 N8 124.2(7) . . ?
N9 C2 C1 129.3(8) . . ?
C1 C2 N8 106.6(6) . . ?
N9 C3 H3 117.1 . . ?
N9 C3 C4 125.8(8) . . ?
C4 C3 H3 117.1 . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 C3 118.6(8) . . ?
C5 C4 H4A 120.7 . . ?
N8 C5 C4 117.0(8) . . ?
N8 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
N8 C6 N10 107.6(6) . . ?
N8 C6 C7 128.4(7) . . ?
N10 C6 C7 124.0(6) . . ?
N11 C7 N12 129.7(7) . . ?
N11 C7 C6 114.8(7) . . ?
N12 C7 C6 115.5(6) . . ?
N11 C8 H8 119.2 . . ?
C9 C8 N11 121.6(7) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(8) . . ?
C10 C9 H9 119.8 . . ?
N12 C10 C9 119.4(8) . . ?
N12 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C11 C12 N2 175.3(7) . . . . ?
N1 C11 C12 N3 -5.2(13) . . . . ?
N2 C16 C17 N5 177.8(7) . . . . ?
N2 C16 C17 N6 -3.6(11) . . . . ?
N3 C13 C14 C15 0.7(12) . . . . ?
N4 C11 C12 N2 -0.7(7) . . . . ?
N4 C11 C12 N3 178.8(7) . . . . ?
N4 C16 C17 N5 0.7(10) . . . . ?
N4 C16 C17 N6 179.3(7) . . . . ?
N5 C18 C19 C20 -0.1(11) . . . . ?
C11 N4 C16 N2 0.0(8) . . . . ?
C11 N4 C16 C17 177.7(6) . . . . ?
C12 N2 C15 C14 -2.5(10) . . . . ?
C12 N2 C16 N4 -0.4(7) . . . . ?
C12 N2 C16 C17 -178.0(7) . . . . ?
C12 N3 C13 C14 -0.5(11) . . . . ?
C13 N3 C12 N2 -1.3(10) . . . . ?
C13 N3 C12 C11 179.4(7) . . . . ?
C13 C14 C15 N2 0.8(11) . . . . ?
C15 N2 C12 N3 2.9(10) . . . . ?
C15 N2 C12 C11 -177.7(6) . . . . ?
C15 N2 C16 N4 177.7(7) . . . . ?
C15 N2 C16 C17 0.1(12) . . . . ?
C16 N2 C12 N3 -178.8(6) . . . . ?
C16 N2 C12 C11 0.7(7) . . . . ?
C16 N2 C15 C14 179.6(7) . . . . ?
C16 N4 C11 N1 -175.8(7) . . . . ?
C16 N4 C11 C12 0.4(8) . . . . ?
C17 N5 C18 C19 -0.7(11) . . . . ?
C17 N6 C20 C19 2.1(11) . . . . ?
C18 N5 C17 N6 2.5(11) . . . . ?
C18 N5 C17 C16 -179.0(6) . . . . ?
C18 C19 C20 N6 -0.7(12) . . . . ?
C20 N6 C17 N5 -3.2(11) . . . . ?
C20 N6 C17 C16 178.4(7) . . . . ?
N7 C1 C2 N8 -177.4(8) . . . . ?
N7 C1 C2 N9 3.1(14) . . . . ?
N8 C6 C7 N11 -178.1(7) . . . . ?
N8 C6 C7 N12 1.9(11) . . . . ?
N9 C3 C4 C5 -1.0(13) . . . . ?
N10 C1 C2 N8 -0.9(8) . . . . ?
N10 C1 C2 N9 179.6(7) . . . . ?
N10 C6 C7 N11 1.2(10) . . . . ?
N10 C6 C7 N12 -178.7(6) . . . . ?
N11 C8 C9 C10 2.6(12) . . . . ?
C1 N10 C6 N8 -0.6(8) . . . . ?
C1 N10 C6 C7 179.9(7) . . . . ?
C2 N8 C5 C4 0.6(10) . . . . ?
C2 N8 C6 N10 0.0(8) . . . . ?
C2 N8 C6 C7 179.5(7) . . . . ?
C2 N9 C3 C4 1.2(12) . . . . ?
C3 N9 C2 N8 -0.4(11) . . . . ?
C3 N9 C2 C1 179.1(8) . . . . ?
C3 C4 C5 N8 0.0(11) . . . . ?
C5 N8 C2 N9 -0.5(11) . . . . ?
C5 N8 C2 C1 180.0(6) . . . . ?
C5 N8 C6 N10 -179.3(7) . . . . ?
C5 N8 C6 C7 0.2(13) . . . . ?
C6 N8 C2 N9 -179.9(7) . . . . ?
C6 N8 C2 C1 0.5(8) . . . . ?
C6 N8 C5 C4 179.9(7) . . . . ?
C6 N10 C1 N7 177.5(7) . . . . ?
C6 N10 C1 C2 0.9(8) . . . . ?
C7 N11 C8 C9 -2.6(11) . . . . ?
C7 N12 C10 C9 -0.7(11) . . . . ?
C8 N11 C7 N12 1.1(11) . . . . ?
C8 N11 C7 C6 -178.9(6) . . . . ?
C8 C9 C10 N12 -0.8(12) . . . . ?
C10 N12 C7 N11 0.5(12) . . . . ?
C10 N12 C7 C6 -179.5(7) . . . . ?

_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_mo_d8_4092_18feb20_ajp2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2182003'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H I3), 2(C12 H9 N4 S), 2(I)'
_chemical_formula_sum            'C26 H20 I8 N8 S2'
_chemical_formula_weight         1523.82
_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'
S S 0.1246 0.1234 '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                   8.7340(4)
_cell_length_b                   14.0058(6)
_cell_length_c                   16.2738(8)
_cell_angle_alpha                109.150(2)
_cell_angle_beta                 90.654(2)
_cell_angle_gamma                96.535(2)
_cell_volume                     1865.82(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9767
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.538
_shelx_estimated_absorpt_T_min   0.281
_exptl_absorpt_coefficient_mu    6.793
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.712
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.104
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47569
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.405
_diffrn_reflns_theta_min         2.350
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7099
_reflns_number_total             7641
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         7641
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0161
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0095P)²+2.0323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0328
_refine_ls_wR_factor_ref         0.0341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N4-HN4 = N3-HN3 = N8-HN8 = N7-HN7
 0.88 with sigma of 0.02
 C19-S2A \\sim C13-S2B
 with sigma of 0.01
 C13-N6A \\sim C19-N6B
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
C13 \\sim S2B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C19 \\sim N6B: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
3. Others
 Sof(S2B)=Sof(N6B)=1-FVAR(1)
 Sof(S2A)=Sof(N6A)=FVAR(1)
 Fixed Sof: HN7(0.5) HN8(0.5) HN3(0.5) HN4(0.5)
4.a Ternary CH refined with riding coordinates:
 C25(H25), C26(H26)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I -0.32806(2) 0.68383(2) 0.06350(2) 0.01662(4) Uani 1 1 d . . . . .
HN7 H 0.626(7) 0.869(4) 0.760(4) 0.020 Uiso 0.5 1 d D U P A 4
HN8 H 0.600(7) 0.466(4) 0.305(4) 0.020 Uiso 0.5 1 d D U P B 2
I2 I -0.15281(2) 0.69172(2) 0.26459(2) 0.01712(4) Uani 1 1 d . . . . .
I3 I -0.19778(2) 0.46050(2) 0.08464(2) 0.01966(4) Uani 1 1 d . . . . .
C25 C -0.1568(3) 0.6249(2) 0.12439(19) 0.0180(6) Uani 1 1 d . . . . .
H25 H -0.053379 0.644261 0.104733 0.022 Uiso 1 1 calc R U . . .
I4 I -0.18763(2) 0.77425(2) 0.49203(2) 0.01962(4) Uani 1 1 d . . . . .
I5 I -0.00642(2) 0.94319(2) 0.68840(2) 0.01594(4) Uani 1 1 d . . . . .
I6 I -0.09061(2) 1.12257(2) 0.88994(2) 0.01577(4) Uani 1 1 d . . . . .
I7 I 0.20431(2) 0.96500(2) 0.88464(2) 0.01693(4) Uani 1 1 d . . . . .
C26 C 0.0870(3) 1.0446(2) 0.81420(19) 0.0173(6) Uani 1 1 d . . . . .
H26 H 0.164805 1.097286 0.804181 0.021 Uiso 1 1 calc R U . . .
I8 I -0.38984(2) 1.20627(2) 1.02268(2) 0.01847(4) Uani 1 1 d . . . . .
S1 S 0.21651(9) 0.94057(6) 0.43631(5) 0.02406(17) Uani 1 1 d . . . . .
N1 N 0.3702(3) 0.80444(18) 0.45092(16) 0.0164(5) Uani 1 1 d . . . . .
N2 N 0.2203(3) 0.84335(19) 0.34927(16) 0.0195(5) Uani 1 1 d . . . . .
N3 N 0.4681(3) 0.53594(19) 0.26644(16) 0.0181(5) Uani 1 1 d D . . . .
N4 N 0.5245(3) 0.94313(19) 0.71296(17) 0.0178(5) Uani 1 1 d D . . . .
C1 C 0.3086(3) 0.7790(2) 0.3691(2) 0.0175(6) Uani 1 1 d . . . . .
C2 C 0.3419(3) 0.6843(2) 0.30258(19) 0.0167(6) Uani 1 1 d . . . . .
C3 C 0.4373(3) 0.6230(2) 0.32512(19) 0.0177(6) Uani 1 1 d . . . . .
H3A H 0.481204 0.643128 0.382853 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4106(3) 0.5048(2) 0.1838(2) 0.0204(6) Uani 1 1 d . . . . .
H4A H 0.433815 0.442330 0.143635 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3171(4) 0.5640(2) 0.1574(2) 0.0237(7) Uani 1 1 d . . . . .
H5 H 0.277120 0.542668 0.098780 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2823(3) 0.6542(2) 0.2165(2) 0.0221(7) Uani 1 1 d . . . . .
H6 H 0.218592 0.695370 0.198805 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3328(3) 0.8950(2) 0.49683(19) 0.0167(6) Uani 1 1 d . . . . .
C8 C 0.3891(3) 0.9497(2) 0.58685(19) 0.0156(6) Uani 1 1 d . . . . .
C9 C 0.4696(3) 0.8987(2) 0.63064(19) 0.0167(6) Uani 1 1 d . . . . .
H9 H 0.485813 0.830247 0.600914 0.020 Uiso 1 1 calc R U . . .
C10 C 0.5043(3) 1.0404(2) 0.7559(2) 0.0173(6) Uani 1 1 d . . . . .
H10 H 0.543345 1.071516 0.814545 0.021 Uiso 1 1 calc R U . . .
C11 C 0.4274(3) 1.0961(2) 0.7159(2) 0.0185(6) Uani 1 1 d . . . . .
H11 H 0.415861 1.165178 0.746706 0.022 Uiso 1 1 calc R U . . .
C12 C 0.3675(3) 1.0507(2) 0.6309(2) 0.0179(6) Uani 1 1 d . . . . .
H12 H 0.312903 1.087584 0.603207 0.021 Uiso 1 1 calc R U . . .
HN3 H 0.526(6) 0.499(4) 0.284(4) 0.021 Uiso 0.5 1 d D U P C 1
HN4 H 0.567(7) 0.904(4) 0.736(4) 0.021 Uiso 0.5 1 d D U P D 3
N5 N 0.7639(3) 0.55467(18) 0.59677(15) 0.0158(5) Uani 1 1 d . . . . .
N7 N 0.6703(3) 0.82722(18) 0.77924(16) 0.0168(5) Uani 1 1 d D . . . .
N8 N 0.6428(3) 0.42780(19) 0.32956(16) 0.0181(5) Uani 1 1 d D . . . .
C13 C 0.8308(3) 0.5847(2) 0.67809(19) 0.0158(6) Uani 1 1 d D U . . .
C14 C 0.7968(3) 0.6789(2) 0.74452(19) 0.0157(6) Uani 1 1 d . . . . .
C15 C 0.7062(3) 0.7414(2) 0.72067(19) 0.0166(6) Uani 1 1 d . . . . .
H15 H 0.668841 0.723110 0.661798 0.020 Uiso 1 1 calc R U . . .
C16 C 0.7220(3) 0.8557(2) 0.86232(19) 0.0186(6) Uani 1 1 d . . . . .
H16 H 0.693412 0.916139 0.903058 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8170(4) 0.7980(2) 0.88985(19) 0.0204(6) Uani 1 1 d . . . . .
H17 H 0.855245 0.819273 0.948772 0.025 Uiso 1 1 calc R U . . .
C18 C 0.8552(3) 0.7091(2) 0.8305(2) 0.0198(6) Uani 1 1 d . . . . .
H18 H 0.920756 0.668930 0.848065 0.024 Uiso 1 1 calc R U . . .
C19 C 0.8171(3) 0.4694(2) 0.54913(18) 0.0150(6) Uani 1 1 d D U . . .
C20 C 0.7730(3) 0.4193(2) 0.45685(19) 0.0163(6) Uani 1 1 d . . . . .
C21 C 0.6822(3) 0.4667(2) 0.41449(19) 0.0173(6) Uani 1 1 d . . . . .
H21 H 0.647126 0.529077 0.447508 0.021 Uiso 1 1 calc R U . . .
C22 C 0.6920(3) 0.3396(2) 0.2821(2) 0.0204(6) Uani 1 1 d . . . . .
H22 H 0.664497 0.312117 0.221530 0.024 Uiso 1 1 calc R U . . .
C23 C 0.7815(4) 0.2881(2) 0.3194(2) 0.0218(6) Uani 1 1 d . . . . .
H23 H 0.814491 0.225713 0.284757 0.026 Uiso 1 1 calc R U . . .
C24 C 0.8232(3) 0.3277(2) 0.4076(2) 0.0196(6) Uani 1 1 d . . . . .
H24 H 0.884900 0.292969 0.434067 0.024 Uiso 1 1 calc R U . . .
S2A S 0.94430(16) 0.42962(11) 0.60853(8) 0.0178(3) Uani 0.836(4) 1 d D . P E 1
N6A N 0.9276(7) 0.5271(4) 0.6972(4) 0.0151(11) Uani 0.836(4) 1 d D . P E 1
S2B S 0.9533(11) 0.5064(7) 0.6915(8) 0.0157(12) Uani 0.164(4) 1 d D U P E 2
N6B N 0.914(3) 0.431(2) 0.5893(16) 0.018(3) Uani 0.164(4) 1 d D U P E 2


_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
I1 C25 2.164(3) . ?
I2 C25 2.162(3) . ?
I3 C25 2.163(3) . ?
C25 H25 1.0000 . ?
I5 C26 2.160(3) . ?
I6 C26 2.160(3) . ?
I7 C26 2.163(3) . ?
C26 H26 1.0000 . ?
S1 N2 1.615(3) . ?
S1 C7 1.716(3) . ?
N1 C1 1.349(4) . ?
N1 C7 1.324(4) . ?
N2 C1 1.361(4) . ?
N3 C3 1.337(4) . ?
N3 C4 1.341(4) . ?
N3 HN3 0.87(2) . ?
N4 C9 1.335(4) . ?
N4 C10 1.345(4) . ?
N4 HN4 0.87(2) . ?
C1 C2 1.473(4) . ?
C2 C3 1.389(4) . ?
C2 C6 1.399(4) . ?
C3 H3A 0.9500 . ?
C4 H4A 0.9500 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.461(4) . ?
C8 C9 1.395(4) . ?
C8 C12 1.396(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.387(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9500 . ?
N5 C13 1.353(4) . ?
N5 C19 1.330(4) . ?
N7 HN7 0.87(2) . ?
N7 C15 1.339(4) . ?
N7 C16 1.335(4) . ?
N8 HN8 0.88(2) . ?
N8 C21 1.333(4) . ?
N8 C22 1.345(4) . ?
C13 C14 1.470(4) . ?
C13 N6A 1.333(6) . ?
C13 S2B 1.677(7) . ?
C14 C15 1.384(4) . ?
C14 C18 1.394(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.459(4) . ?
C19 S2A 1.717(3) . ?
C19 N6B 1.330(11) . ?
C20 C21 1.398(4) . ?
C20 C24 1.394(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(4) . ?
C24 H24 0.9500 . ?
S2A N6A 1.651(6) . ?
S2B N6B 1.66(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 C25 H25 108.1 . . ?
I2 C25 I1 110.79(13) . . ?
I2 C25 I3 110.84(13) . . ?
I2 C25 H25 108.1 . . ?
I3 C25 I1 110.92(13) . . ?
I3 C25 H25 108.1 . . ?
I5 C26 I7 111.56(12) . . ?
I5 C26 H26 107.7 . . ?
I6 C26 I5 111.05(12) . . ?
I6 C26 I7 110.98(13) . . ?
I6 C26 H26 107.7 . . ?
I7 C26 H26 107.7 . . ?
N2 S1 C7 93.59(14) . . ?
C7 N1 C1 108.5(2) . . ?
C1 N2 S1 107.4(2) . . ?
C3 N3 C4 121.9(3) . . ?
C3 N3 HN3 117(5) . . ?
C4 N3 HN3 121(5) . . ?
C9 N4 C10 119.9(3) . . ?
C9 N4 HN4 115(5) . . ?
C10 N4 HN4 125(5) . . ?
N1 C1 N2 119.0(3) . . ?
N1 C1 C2 119.5(2) . . ?
N2 C1 C2 121.5(3) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 C6 118.4(3) . . ?
C6 C2 C1 122.2(3) . . ?
N3 C3 C2 120.7(3) . . ?
N3 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
N3 C4 H4A 120.1 . . ?
N3 C4 C5 119.8(3) . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C2 C6 H6 120.4 . . ?
C5 C6 C2 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
N1 C7 S1 111.5(2) . . ?
N1 C7 C8 123.5(3) . . ?
C8 C7 S1 125.0(2) . . ?
C9 C8 C7 118.4(3) . . ?
C9 C8 C12 118.4(3) . . ?
C12 C8 C7 123.2(3) . . ?
N4 C9 C8 122.1(3) . . ?
N4 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
N4 C10 H10 119.5 . . ?
N4 C10 C11 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C8 C12 H12 120.6 . . ?
C11 C12 C8 118.7(3) . . ?
C11 C12 H12 120.6 . . ?
C19 N5 C13 108.7(2) . . ?
C15 N7 HN7 118(5) . . ?
C16 N7 HN7 120(5) . . ?
C16 N7 C15 121.0(3) . . ?
C21 N8 HN8 118(4) . . ?
C21 N8 C22 119.3(3) . . ?
C22 N8 HN8 122(4) . . ?
N5 C13 C14 120.6(2) . . ?
N5 C13 S2B 113.4(5) . . ?
C14 C13 S2B 125.9(5) . . ?
N6A C13 N5 118.9(4) . . ?
N6A C13 C14 120.4(4) . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 C18 118.5(3) . . ?
C18 C14 C13 122.5(3) . . ?
N7 C15 C14 121.0(3) . . ?
N7 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
N7 C16 H16 119.6 . . ?
N7 C16 C17 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H17 120.4 . . ?
C14 C18 H18 120.3 . . ?
C17 C18 C14 119.5(3) . . ?
C17 C18 H18 120.3 . . ?
N5 C19 C20 122.6(2) . . ?
N5 C19 S2A 111.9(2) . . ?
C20 C19 S2A 125.4(2) . . ?
N6B C19 N5 117.0(12) . . ?
N6B C19 C20 120.4(12) . . ?
C21 C20 C19 119.1(3) . . ?
C24 C20 C19 122.8(3) . . ?
C24 C20 C21 118.1(3) . . ?
N8 C21 C20 122.6(3) . . ?
N8 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
N8 C22 H22 119.2 . . ?
N8 C22 C23 121.5(3) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C20 C24 H24 120.6 . . ?
C23 C24 C20 118.8(3) . . ?
C23 C24 H24 120.6 . . ?
N6A S2A C19 92.1(2) . . ?
C13 N6A S2A 108.3(4) . . ?
N6B S2B C13 90.5(8) . . ?
C19 N6B S2B 110.3(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C26 H26 I1 1.00 3.27 3.997(3) 131.2 2_576 yes
C4 H4A I1 0.95 3.31 4.028(3) 133.5 2_565 yes
C5 H5 I3 0.95 3.04 3.957(3) 162.2 2_565 yes
C10 H10 I6 0.95 3.32 3.981(3) 128.1 1_655 yes
C10 H10 I8 0.95 3.30 4.231(3) 167.2 1_655 yes
C11 H11 I1 0.95 3.28 4.069(3) 142.2 2_576 yes
C11 H11 I2 0.95 3.26 3.963(3) 132.7 2_576 yes
N3 HN3 N8 0.87(2) 1.81(2) 2.681(3) 175(7) . yes
N4 HN4 N7 0.87(2) 1.78(2) 2.647(3) 175(6) . yes
C15 H15 I4 0.95 3.30 4.003(3) 132.4 1_655 yes
C17 H17 I6 0.95 3.14 4.047(3) 159.8 2_677 yes
C22 H22 I8 0.95 3.09 4.035(3) 172.6 1_644 yes
C23 H23 I5 0.95 3.19 3.943(3) 137.8 2_666 yes
C23 H23 I7 0.95 3.13 4.000(3) 152.4 2_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N2 C1 N1 1.0(3) . . . . ?
S1 N2 C1 C2 -177.1(2) . . . . ?
S1 C7 C8 C9 173.5(2) . . . . ?
S1 C7 C8 C12 -7.2(4) . . . . ?
N1 C1 C2 C3 -0.5(4) . . . . ?
N1 C1 C2 C6 -179.5(3) . . . . ?
N1 C7 C8 C9 -8.7(4) . . . . ?
N1 C7 C8 C12 170.6(3) . . . . ?
N2 S1 C7 N1 -1.8(2) . . . . ?
N2 S1 C7 C8 176.2(2) . . . . ?
N2 C1 C2 C3 177.6(3) . . . . ?
N2 C1 C2 C6 -1.4(4) . . . . ?
N3 C4 C5 C6 -0.7(5) . . . . ?
N4 C10 C11 C12 1.2(4) . . . . ?
C1 N1 C7 S1 2.5(3) . . . . ?
C1 N1 C7 C8 -175.6(3) . . . . ?
C1 C2 C3 N3 179.2(3) . . . . ?
C1 C2 C6 C5 -179.5(3) . . . . ?
C3 N3 C4 C5 0.4(4) . . . . ?
C3 C2 C6 C5 1.4(4) . . . . ?
C4 N3 C3 C2 0.9(4) . . . . ?
C4 C5 C6 C2 -0.2(5) . . . . ?
C6 C2 C3 N3 -1.8(4) . . . . ?
C7 S1 N2 C1 0.5(2) . . . . ?
C7 N1 C1 N2 -2.3(4) . . . . ?
C7 N1 C1 C2 175.8(3) . . . . ?
C7 C8 C9 N4 -179.9(3) . . . . ?
C7 C8 C12 C11 -179.1(3) . . . . ?
C9 N4 C10 C11 -0.2(4) . . . . ?
C9 C8 C12 C11 0.3(4) . . . . ?
C10 N4 C9 C8 -0.8(4) . . . . ?
C10 C11 C12 C8 -1.2(4) . . . . ?
C12 C8 C9 N4 0.8(4) . . . . ?
N5 C13 C14 C15 -5.8(4) . . . . ?
N5 C13 C14 C18 175.7(3) . . . . ?
N5 C13 N6A S2A 1.9(6) . . . . ?
N5 C13 S2B N6B -1.2(12) . . . . ?
N5 C19 C20 C21 5.7(4) . . . . ?
N5 C19 C20 C24 -177.2(3) . . . . ?
N5 C19 S2A N6A -0.3(3) . . . . ?
N5 C19 N6B S2B -3(2) . . . . ?
N7 C16 C17 C18 -1.3(4) . . . . ?
N8 C22 C23 C24 -0.4(5) . . . . ?
C13 N5 C19 C20 -177.2(3) . . . . ?
C13 N5 C19 S2A 1.3(3) . . . . ?
C13 N5 C19 N6B 2.6(15) . . . . ?
C13 C14 C15 N7 179.0(3) . . . . ?
C13 C14 C18 C17 -179.2(3) . . . . ?
C13 S2B N6B C19 2.5(18) . . . . ?
C14 C13 N6A S2A -178.4(3) . . . . ?
C14 C13 S2B N6B -179.8(10) . . . . ?
C15 N7 C16 C17 1.3(4) . . . . ?
C15 C14 C18 C17 2.3(4) . . . . ?
C16 N7 C15 C14 0.6(4) . . . . ?
C16 C17 C18 C14 -0.5(4) . . . . ?
C18 C14 C15 N7 -2.4(4) . . . . ?
C19 N5 C13 C14 178.2(3) . . . . ?
C19 N5 C13 N6A -2.1(5) . . . . ?
C19 N5 C13 S2B -0.5(5) . . . . ?
C19 C20 C21 N8 177.1(3) . . . . ?
C19 C20 C24 C23 -176.9(3) . . . . ?
C19 S2A N6A C13 -0.9(4) . . . . ?
C20 C19 S2A N6A 178.2(3) . . . . ?
C20 C19 N6B S2B 176.3(9) . . . . ?
C21 N8 C22 C23 0.4(4) . . . . ?
C21 C20 C24 C23 0.2(4) . . . . ?
C22 N8 C21 C20 -0.1(4) . . . . ?
C22 C23 C24 C20 0.1(5) . . . . ?
C24 C20 C21 N8 -0.2(4) . . . . ?
S2A C19 C20 C21 -172.6(2) . . . . ?
S2A C19 C20 C24 4.6(4) . . . . ?
N6A C13 C14 C15 174.6(4) . . . . ?
N6A C13 C14 C18 -3.9(5) . . . . ?
S2B C13 C14 C15 172.8(5) . . . . ?
S2B C13 C14 C18 -5.7(6) . . . . ?
N6B C19 C20 C21 -174.1(15) . . . . ?
N6B C19 C20 C24 3.1(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT434_mo_d8_4092_18feb20_ajp2_0m_a 
;
PROBLEM: Short Inter HL..HL Contact I6       ..I8       .       3.47 Ang.  
RESPONSE: This contact represents an I...I halogen bond
;
####################################################################### 
# 
# 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_mo_d8_5481_26sep21_ajp3_0m
_database_code_depnum_ccdc_archive 'CCDC 2182016'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi4 I16, 2(I2), 2(C28 H28 N8), 4(C2 H3 N)'
_chemical_formula_sum            'C64 H68 Bi4 I20 N20'
_chemical_formula_weight         4491.30
_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      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                   11.1882(5)
_cell_length_b                   14.4203(6)
_cell_length_c                   17.1240(8)
_cell_angle_alpha                109.244(2)
_cell_angle_beta                 91.431(2)
_cell_angle_gamma                97.814(2)
_cell_volume                     2576.9(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9595
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.405
_shelx_estimated_absorpt_T_min   0.238
_exptl_absorpt_coefficient_mu    12.844
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.894
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            127858
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.645
_diffrn_reflns_theta_min         2.155
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12797
_reflns_number_total             14514
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         2.745
_refine_diff_density_min         -3.268
_refine_diff_density_rms         0.211
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         14514
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0096P)²+22.2653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N5-HN5
 0.86 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 N6(HN6), C3(H3), C4(H4A), C5(H5), C10(H10), C11(H11), C12(H12), C17(H17),
 C18(H18), C19(H19), C24(H24), C25(H25), C26(H26)
2.b X=CH2 refined with riding coordinates:
 N7(HN7A,HN7B)
2.c Idealised Me refined as rotating group:
 C7(H7C,H7D,H7E), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C28(H28A,H28B,
 H28C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
;
_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 0.58758(2) 0.44685(2) 0.86655(2) 0.01602(4) Uani 1 1 d . . . . .
Bi2 Bi 0.32433(2) 0.68981(2) 0.92618(2) 0.01970(4) Uani 1 1 d . . . . .
I1 I 0.58716(3) 0.25704(3) 0.73993(2) 0.02701(8) Uani 1 1 d . . . . .
I2 I 0.81239(3) 0.42905(3) 0.96246(2) 0.02266(7) Uani 1 1 d . . . . .
I3 I 0.73236(3) 0.55220(3) 0.77446(2) 0.02623(8) Uani 1 1 d . . . . .
I4 I 0.57499(3) 0.66235(2) 1.01702(2) 0.01739(6) Uani 1 1 d . . . . .
I5 I 0.34092(3) 0.47268(2) 0.79682(2) 0.02257(7) Uani 1 1 d . . . . .
I6 I 0.33167(6) 0.89683(3) 1.03293(3) 0.05460(15) Uani 1 1 d . . . . .
I7 I 0.08356(4) 0.67343(4) 0.85003(3) 0.04166(11) Uani 1 1 d . . . . .
I8 I 0.46777(4) 0.76593(3) 0.81059(3) 0.02948(8) Uani 1 1 d . . . . .
I9 I 0.37382(4) 0.65714(3) 0.61412(3) 0.03986(11) Uani 1 1 d . . . . .
I10 I 0.32083(4) 0.58592(4) 0.44457(4) 0.04637(12) Uani 1 1 d . . . . .
N1 N 0.7701(4) 0.0136(3) 0.4598(3) 0.0188(8) Uani 1 1 d . . . . .
N2 N 0.7504(4) 0.0492(3) 0.6741(3) 0.0158(8) Uani 1 1 d . . . . .
N3 N 0.8771(4) 0.1054(3) 0.5957(3) 0.0180(8) Uani 1 1 d . . . . .
N4 N 0.9629(4) 0.1284(4) 0.8018(3) 0.0254(10) Uani 1 1 d . . . . .
N5 N 0.9541(4) 0.1114(3) 0.4481(3) 0.0195(8) Uani 1 1 d D . . . .
HN5 H 0.962(6) 0.142(4) 0.5006(14) 0.022(16) Uiso 1 1 d D . . . .
N6 N 0.8167(4) 0.1026(4) 0.3001(3) 0.0231(9) Uani 1 1 d . . . . .
HN6 H 0.852633 0.160863 0.333408 0.028 Uiso 1 1 calc R U . . .
N7 N 1.0557(3) 0.0734(3) 0.3312(2) 0.0116(7) Uani 1 1 d . . . . .
HN7A H 0.994552 0.027009 0.305795 0.014 Uiso 1 1 calc R U . . .
HN7B H 1.119596 0.083328 0.304372 0.014 Uiso 1 1 calc R U . . .
N8 N 1.1413(4) 0.2320(3) 0.5342(3) 0.0227(9) Uani 1 1 d . . . . .
C1 C 0.7857(4) 0.0384(4) 0.5448(3) 0.0178(9) Uani 1 1 d . . . . .
C2 C 0.7032(4) 0.0018(3) 0.5925(3) 0.0158(9) Uani 1 1 d . . . . .
C3 C 0.6898(5) 0.0385(4) 0.7407(3) 0.0208(10) Uani 1 1 d . . . . .
H3 H 0.723374 0.072574 0.795957 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5820(5) -0.0214(4) 0.7259(3) 0.0229(10) Uani 1 1 d . . . . .
H4A H 0.538573 -0.028962 0.770891 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5330(5) -0.0733(4) 0.6426(4) 0.0227(10) Uani 1 1 d . . . . .
H5 H 0.457420 -0.115754 0.633316 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5908(5) -0.0640(4) 0.5763(3) 0.0201(10) Uani 1 1 d . . . . .
C7 C 0.5415(5) -0.1204(4) 0.4885(3) 0.0239(11) Uani 1 1 d . . . . .
H7C H 0.545338 -0.074964 0.456567 0.036 Uiso 1 1 calc R U . . .
H7D H 0.457166 -0.150036 0.488191 0.036 Uiso 1 1 calc R U . . .
H7E H 0.589681 -0.173113 0.463442 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8560(4) 0.1109(4) 0.6725(3) 0.0178(9) Uani 1 1 d . . . . .
C9 C 0.9324(4) 0.1725(4) 0.7462(3) 0.0192(10) Uani 1 1 d . . . . .
C10 C 1.0295(6) 0.1783(5) 0.8733(4) 0.0332(13) Uani 1 1 d . . . . .
H10 H 1.047244 0.144646 0.910473 0.040 Uiso 1 1 calc R U . . .
C11 C 1.0719(5) 0.2775(5) 0.8929(4) 0.0352(14) Uani 1 1 d . . . . .
H11 H 1.118663 0.313452 0.943638 0.042 Uiso 1 1 calc R U . . .
C12 C 1.0455(5) 0.3242(4) 0.8376(4) 0.0304(13) Uani 1 1 d . . . . .
H12 H 1.075694 0.392772 0.850487 0.036 Uiso 1 1 calc R U . . .
C13 C 0.9755(5) 0.2738(4) 0.7630(3) 0.0224(10) Uani 1 1 d . . . . .
C14 C 0.9441(6) 0.3268(4) 0.7056(4) 0.0294(12) Uani 1 1 d . . . . .
H14A H 0.985843 0.303517 0.654657 0.044 Uiso 1 1 calc R U . . .
H14B H 0.969412 0.398446 0.732457 0.044 Uiso 1 1 calc R U . . .
H14C H 0.856502 0.313200 0.691828 0.044 Uiso 1 1 calc R U . . .
C15 C 0.8464(4) 0.0472(4) 0.4169(3) 0.0178(9) Uani 1 1 d . . . . .
C16 C 0.8072(5) 0.0244(4) 0.3288(3) 0.0188(9) Uani 1 1 d . . . . .
C17 C 0.7748(6) 0.0959(5) 0.2247(4) 0.0295(12) Uani 1 1 d . . . . .
H17 H 0.785416 0.152766 0.207737 0.035 Uiso 1 1 calc R U . . .
C18 C 0.7166(5) 0.0070(5) 0.1719(4) 0.0303(12) Uani 1 1 d . . . . .
H18 H 0.683534 0.001935 0.118763 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7064(5) -0.0757(4) 0.1969(4) 0.0279(12) Uani 1 1 d . . . . .
H19 H 0.667131 -0.137961 0.159996 0.033 Uiso 1 1 calc R U . . .
C20 C 0.7530(5) -0.0694(4) 0.2761(3) 0.0224(10) Uani 1 1 d . . . . .
C21 C 0.7505(5) -0.1588(4) 0.3014(4) 0.0254(11) Uani 1 1 d . . . . .
H21A H 0.825855 -0.153484 0.334098 0.038 Uiso 1 1 calc R U . . .
H21B H 0.742243 -0.218392 0.251874 0.038 Uiso 1 1 calc R U . . .
H21C H 0.681714 -0.163517 0.334968 0.038 Uiso 1 1 calc R U . . .
C22 C 1.0520(4) 0.1236(4) 0.4029(3) 0.0183(9) Uani 1 1 d . . . . .
C23 C 1.1487(5) 0.2060(4) 0.4525(3) 0.0202(10) Uani 1 1 d . . . . .
C24 C 1.2233(5) 0.3062(4) 0.5844(4) 0.0262(11) Uani 1 1 d . . . . .
H24 H 1.220147 0.323711 0.642810 0.031 Uiso 1 1 calc R U . . .
C25 C 1.3127(5) 0.3577(4) 0.5526(4) 0.0311(13) Uani 1 1 d . . . . .
H25 H 1.370368 0.409616 0.588755 0.037 Uiso 1 1 calc R U . . .
C26 C 1.3158(5) 0.3324(4) 0.4689(4) 0.0302(13) Uani 1 1 d . . . . .
H26 H 1.374966 0.368700 0.446921 0.036 Uiso 1 1 calc R U . . .
C27 C 1.2344(5) 0.2546(4) 0.4145(4) 0.0221(10) Uani 1 1 d . . . . .
C28 C 1.2372(6) 0.2302(4) 0.3222(4) 0.0297(12) Uani 1 1 d . . . . .
H28A H 1.295417 0.280276 0.310455 0.045 Uiso 1 1 calc R U . . .
H28B H 1.156539 0.230035 0.298396 0.045 Uiso 1 1 calc R U . . .
H28C H 1.261328 0.164536 0.297689 0.045 Uiso 1 1 calc R U . . .
N9 N 0.9471(5) 0.3004(4) 0.3771(4) 0.0346(12) Uani 1 1 d . . . . .
C29 C 0.9506(6) 0.3822(5) 0.3836(4) 0.0345(14) Uani 1 1 d . . . . .
C30 C 0.9505(7) 0.4852(5) 0.3898(6) 0.0490(19) Uani 1 1 d . . . . .
H30A H 0.910605 0.487626 0.339068 0.074 Uiso 1 1 calc R U . . .
H30B H 1.034043 0.519358 0.396992 0.074 Uiso 1 1 calc R U . . .
H30C H 0.906798 0.518118 0.437589 0.074 Uiso 1 1 calc R U . . .
N10 N 1.0556(7) 0.0394(5) 0.1395(4) 0.0532(17) Uani 1 1 d . . . . .
C31 C 1.1119(7) 0.0900(5) 0.1117(4) 0.0388(15) Uani 1 1 d . . . . .
C32 C 1.1866(7) 0.1551(6) 0.0766(5) 0.0473(18) Uani 1 1 d . . . . .
H32A H 1.203163 0.117132 0.020028 0.071 Uiso 1 1 calc R U . . .
H32B H 1.263044 0.182290 0.110780 0.071 Uiso 1 1 calc R U . . .
H32C H 1.143765 0.209641 0.075515 0.071 Uiso 1 1 calc R U . . .


_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 2.8769(4) . ?
Bi1 I2 3.0556(4) . ?
Bi1 I3 2.9079(4) . ?
Bi1 I4 3.3519(4) 2_667 ?
Bi1 I4 3.3430(4) . ?
Bi1 I5 3.0965(4) . ?
Bi2 I2 3.2406(4) 2_667 ?
Bi2 I4 3.3063(4) . ?
Bi2 I5 3.2175(4) . ?
Bi2 I6 2.9306(5) . ?
Bi2 I7 2.9088(5) . ?
Bi2 I8 2.9681(4) . ?
I9 I10 2.7602(8) . ?
N1 C1 1.380(6) . ?
N1 C15 1.287(6) . ?
N2 C2 1.391(6) . ?
N2 C3 1.383(6) . ?
N2 C8 1.385(6) . ?
N3 C1 1.368(6) . ?
N3 C8 1.321(6) . ?
N4 C9 1.365(7) . ?
N4 C10 1.342(7) . ?
N5 HN5 0.86(2) . ?
N5 C15 1.390(6) . ?
N5 C22 1.382(6) . ?
N6 HN6 0.8800 . ?
N6 C16 1.363(7) . ?
N6 C17 1.331(7) . ?
N7 HN7A 0.8800 . ?
N7 HN7B 0.8800 . ?
N7 C22 1.207(6) . ?
N8 C23 1.332(7) . ?
N8 C24 1.346(7) . ?
C1 C2 1.409(7) . ?
C2 C6 1.429(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.349(8) . ?
C4 H4A 0.9500 . ?
C4 C5 1.429(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.355(7) . ?
C6 C7 1.503(8) . ?
C7 H7C 0.9800 . ?
C7 H7D 0.9800 . ?
C7 H7E 0.9800 . ?
C8 C9 1.454(7) . ?
C9 C13 1.405(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.398(8) . ?
C13 C14 1.493(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.475(7) . ?
C16 C20 1.399(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.366(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.410(8) . ?
C20 C21 1.488(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.497(7) . ?
C23 C27 1.409(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.360(9) . ?
C26 H26 0.9500 . ?
C26 C27 1.395(8) . ?
C27 C28 1.504(8) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N9 C29 1.142(8) . ?
C29 C30 1.454(9) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N10 C31 1.129(10) . ?
C31 C32 1.457(10) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Bi1 I2 93.259(12) . . ?
I1 Bi1 I3 92.688(13) . . ?
I1 Bi1 I4 90.637(11) . 2_667 ?
I1 Bi1 I4 177.019(11) . . ?
I1 Bi1 I5 92.606(12) . . ?
I2 Bi1 I4 86.925(10) . 2_667 ?
I2 Bi1 I4 87.801(10) . . ?
I2 Bi1 I5 170.648(11) . . ?
I3 Bi1 I2 91.883(12) . . ?
I3 Bi1 I4 176.527(12) . 2_667 ?
I3 Bi1 I4 90.061(11) . . ?
I3 Bi1 I5 95.113(12) . . ?
I4 Bi1 I4 86.635(9) . 2_667 ?
I5 Bi1 I4 85.732(10) . 2_667 ?
I5 Bi1 I4 85.995(10) . . ?
I2 Bi2 I4 84.753(10) 2_667 . ?
I5 Bi2 I2 85.192(11) . 2_667 ?
I5 Bi2 I4 84.699(10) . . ?
I6 Bi2 I2 101.504(14) . 2_667 ?
I6 Bi2 I4 93.938(15) . . ?
I6 Bi2 I5 173.036(15) . . ?
I6 Bi2 I8 87.737(15) . . ?
I7 Bi2 I2 84.813(12) . 2_667 ?
I7 Bi2 I4 167.726(13) . . ?
I7 Bi2 I5 88.001(14) . . ?
I7 Bi2 I6 94.462(18) . . ?
I7 Bi2 I8 98.733(13) . . ?
I8 Bi2 I2 169.868(12) . 2_667 ?
I8 Bi2 I4 90.524(11) . . ?
I8 Bi2 I5 85.449(12) . . ?
Bi1 I2 Bi2 97.482(11) . 2_667 ?
Bi1 I4 Bi1 93.365(10) . 2_667 ?
Bi2 I4 Bi1 90.648(9) . 2_667 ?
Bi2 I4 Bi1 91.254(9) . . ?
Bi1 I5 Bi2 97.644(11) . . ?
C15 N1 C1 123.2(5) . . ?
C3 N2 C2 122.3(4) . . ?
C3 N2 C8 130.1(4) . . ?
C8 N2 C2 107.4(4) . . ?
C8 N3 C1 107.1(4) . . ?
C10 N4 C9 123.0(5) . . ?
C15 N5 HN5 116(4) . . ?
C22 N5 HN5 118(4) . . ?
C22 N5 C15 125.5(4) . . ?
C16 N6 HN6 118.0 . . ?
C17 N6 HN6 118.0 . . ?
C17 N6 C16 123.9(5) . . ?
HN7A N7 HN7B 120.0 . . ?
C22 N7 HN7A 120.0 . . ?
C22 N7 HN7B 120.0 . . ?
C23 N8 C24 118.8(5) . . ?
N1 C1 C2 123.9(4) . . ?
N3 C1 N1 126.1(4) . . ?
N3 C1 C2 109.9(4) . . ?
N2 C2 C1 104.7(4) . . ?
N2 C2 C6 119.1(4) . . ?
C1 C2 C6 136.1(5) . . ?
N2 C3 H3 120.6 . . ?
C4 C3 N2 118.7(5) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4A 119.9 . . ?
C3 C4 C5 120.2(5) . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.1(5) . . ?
C6 C5 H5 119.0 . . ?
C2 C6 C7 120.1(5) . . ?
C5 C6 C2 117.5(5) . . ?
C5 C6 C7 122.4(5) . . ?
C6 C7 H7C 109.5 . . ?
C6 C7 H7D 109.5 . . ?
C6 C7 H7E 109.5 . . ?
H7C C7 H7D 109.5 . . ?
H7C C7 H7E 109.5 . . ?
H7D C7 H7E 109.5 . . ?
N2 C8 C9 123.8(4) . . ?
N3 C8 N2 110.9(4) . . ?
N3 C8 C9 125.3(4) . . ?
N4 C9 C8 117.5(5) . . ?
N4 C9 C13 118.9(5) . . ?
C13 C9 C8 123.6(5) . . ?
N4 C10 H10 119.9 . . ?
N4 C10 C11 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(6) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 122.1(6) . . ?
C13 C12 H12 119.0 . . ?
C9 C13 C14 121.6(5) . . ?
C12 C13 C9 117.2(5) . . ?
C12 C13 C14 121.1(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 N5 125.8(5) . . ?
N1 C15 C16 115.7(5) . . ?
N5 C15 C16 118.0(4) . . ?
N6 C16 C15 116.7(4) . . ?
N6 C16 C20 118.9(5) . . ?
C20 C16 C15 124.3(5) . . ?
N6 C17 H17 120.2 . . ?
N6 C17 C18 119.6(5) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.1(5) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.3(5) . . ?
C20 C19 H19 119.4 . . ?
C16 C20 C19 117.1(5) . . ?
C16 C20 C21 121.1(5) . . ?
C19 C20 C21 121.8(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C23 112.3(4) . . ?
N7 C22 N5 122.5(5) . . ?
N7 C22 C23 125.1(5) . . ?
N8 C23 C22 114.1(4) . . ?
N8 C23 C27 123.8(5) . . ?
C27 C23 C22 122.0(5) . . ?
N8 C24 H24 119.3 . . ?
N8 C24 C25 121.4(6) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.8(5) . . ?
C26 C25 H25 120.6 . . ?
C25 C26 H26 119.1 . . ?
C25 C26 C27 121.8(5) . . ?
C27 C26 H26 119.1 . . ?
C23 C27 C28 123.9(5) . . ?
C26 C27 C23 115.3(5) . . ?
C26 C27 C28 120.8(5) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N9 C29 C30 177.7(8) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N10 C31 C32 178.9(8) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -176.9(4) . . . . ?
N1 C1 C2 C6 0.4(9) . . . . ?
N1 C15 C16 N6 128.6(5) . . . . ?
N1 C15 C16 C20 -46.2(7) . . . . ?
N2 C2 C6 C5 2.9(7) . . . . ?
N2 C2 C6 C7 -176.6(4) . . . . ?
N2 C3 C4 C5 0.8(8) . . . . ?
N2 C8 C9 N4 48.5(7) . . . . ?
N2 C8 C9 C13 -131.3(5) . . . . ?
N3 C1 C2 N2 -0.7(5) . . . . ?
N3 C1 C2 C6 176.7(5) . . . . ?
N3 C8 C9 N4 -131.2(5) . . . . ?
N3 C8 C9 C13 49.0(8) . . . . ?
N4 C9 C13 C12 -1.5(7) . . . . ?
N4 C9 C13 C14 -179.1(5) . . . . ?
N4 C10 C11 C12 -0.4(9) . . . . ?
N5 C15 C16 N6 -44.1(7) . . . . ?
N5 C15 C16 C20 141.1(5) . . . . ?
N5 C22 C23 N8 18.8(6) . . . . ?
N5 C22 C23 C27 -157.6(5) . . . . ?
N6 C16 C20 C19 -2.9(7) . . . . ?
N6 C16 C20 C21 174.3(5) . . . . ?
N6 C17 C18 C19 -2.5(9) . . . . ?
N7 C22 C23 N8 -162.4(5) . . . . ?
N7 C22 C23 C27 21.3(8) . . . . ?
N8 C23 C27 C26 1.6(8) . . . . ?
N8 C23 C27 C28 -175.3(5) . . . . ?
N8 C24 C25 C26 0.4(9) . . . . ?
C1 N1 C15 N5 0.4(8) . . . . ?
C1 N1 C15 C16 -171.7(4) . . . . ?
C1 N3 C8 N2 -0.8(6) . . . . ?
C1 N3 C8 C9 178.9(5) . . . . ?
C1 C2 C6 C5 -174.2(5) . . . . ?
C1 C2 C6 C7 6.3(9) . . . . ?
C2 N2 C3 C4 1.1(7) . . . . ?
C2 N2 C8 N3 0.4(5) . . . . ?
C2 N2 C8 C9 -179.4(4) . . . . ?
C3 N2 C2 C1 175.0(4) . . . . ?
C3 N2 C2 C6 -2.9(7) . . . . ?
C3 N2 C8 N3 -173.8(5) . . . . ?
C3 N2 C8 C9 6.4(8) . . . . ?
C3 C4 C5 C6 -0.8(8) . . . . ?
C4 C5 C6 C2 -1.1(8) . . . . ?
C4 C5 C6 C7 178.3(5) . . . . ?
C8 N2 C2 C1 0.2(5) . . . . ?
C8 N2 C2 C6 -177.7(4) . . . . ?
C8 N2 C3 C4 174.5(5) . . . . ?
C8 N3 C1 N1 177.1(5) . . . . ?
C8 N3 C1 C2 0.9(6) . . . . ?
C8 C9 C13 C12 178.3(5) . . . . ?
C8 C9 C13 C14 0.7(8) . . . . ?
C9 N4 C10 C11 -1.1(9) . . . . ?
C10 N4 C9 C8 -177.7(5) . . . . ?
C10 N4 C9 C13 2.1(8) . . . . ?
C10 C11 C12 C13 0.9(9) . . . . ?
C11 C12 C13 C9 0.0(8) . . . . ?
C11 C12 C13 C14 177.7(5) . . . . ?
C15 N1 C1 N3 4.7(8) . . . . ?
C15 N1 C1 C2 -179.7(5) . . . . ?
C15 N5 C22 N7 -4.9(8) . . . . ?
C15 N5 C22 C23 173.9(4) . . . . ?
C15 C16 C20 C19 171.8(5) . . . . ?
C15 C16 C20 C21 -11.0(8) . . . . ?
C16 N6 C17 C18 1.2(9) . . . . ?
C17 N6 C16 C15 -173.5(5) . . . . ?
C17 N6 C16 C20 1.6(8) . . . . ?
C17 C18 C19 C20 1.1(9) . . . . ?
C18 C19 C20 C16 1.6(8) . . . . ?
C18 C19 C20 C21 -175.5(5) . . . . ?
C22 N5 C15 N1 158.8(5) . . . . ?
C22 N5 C15 C16 -29.2(7) . . . . ?
C22 C23 C27 C26 177.6(5) . . . . ?
C22 C23 C27 C28 0.6(8) . . . . ?
C23 N8 C24 C25 2.0(8) . . . . ?
C24 N8 C23 C22 -179.3(5) . . . . ?
C24 N8 C23 C27 -3.1(8) . . . . ?
C24 C25 C26 C27 -1.9(9) . . . . ?
C25 C26 C27 C23 1.0(8) . . . . ?
C25 C26 C27 C28 178.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT414_mo_d8_5481_26sep21_ajp3_0m 
;
PROBLEM: Short Intra D-H..H-X       Hn7B     ..H28C     .       1.87 Ang.  
RESPONSE: Steric congestion of the methyl groups causes numerous close interactions
;
_vrf_PLAT430_mo_d8_5481_26sep21_ajp3_0m 
;
PROBLEM: Short Inter D...A Contact  N4       ..N10      .       2.90 Ang.  
RESPONSE: N4 is brought into relatively close proximity to N10 due to its
H-bonding interaction to N7, a part of the same heterocyclic system
;
_vrf_PLAT434_mo_d8_5481_26sep21_ajp3_0m 
;
PROBLEM: Short Inter HL..HL Contact I8       ..I9       .       3.28 Ang.  
RESPONSE: This contact represents an I...I halogen bond
;
# end Validation Reply Form

#===end
####################################################################### 
# 
# 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_mo_d8_4601_21sep20_ajp3_0m_b
_database_code_depnum_ccdc_archive 'CCDC 2182011'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-04-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(Bi6 I22), 4.5(I2), 3(C18 H15 N6), 3(C2 H3 N), 2(H2 O)'
_chemical_formula_sum            'C60 H58 Bi12 I53 N21 O2'
_chemical_formula_weight         10338.73
_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   11.3588(6)
_cell_length_b                   11.5129(6)
_cell_length_c                   34.8748(17)
_cell_angle_alpha                92.184(2)
_cell_angle_beta                 93.977(2)
_cell_angle_gamma                106.355(2)
_cell_volume                     4357.7(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.537
_shelx_estimated_absorpt_T_min   0.311
_exptl_absorpt_coefficient_mu    21.491
_exptl_absorpt_correction_T_max  0.0206
_exptl_absorpt_correction_T_min  0.0048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.940
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4386
_exptl_crystal_size_max          0.071
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            86802
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.127
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                27768
_reflns_number_total             34387
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         2.226
_refine_diff_density_min         -1.452
_refine_diff_density_rms         0.274
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.208(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1349
_refine_ls_number_reflns         34387
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.014
_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)+(0.0488P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1125
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.792(6)
 0.208(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O1-H1O1 = O1-H2O1
 0.84 with sigma of 0.01
 O2-H1O2 = O2-H2O2
 0.84 with sigma of 0.01
 H1O1-H2O1
 1.33 with sigma of 0.02
 H1O2-H2O2
 1.33 with sigma of 0.02
 H1O2-N12 \\sim H1O2-N13
 with sigma of 0.02
 H2O2-N12 \\sim H2O2-N13
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
N18 \\sim C43 \\sim C45: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
N21 \\sim C59 \\sim C60: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
N19 \\sim C49 \\sim C50 \\sim C51 \\sim C52: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
C57 \\sim C58: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
N20 \\sim C55 \\sim C56: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
5.a Aromatic/amide H refined with riding coordinates:
 N4(HN4), N5(HN5), N6(HN6), C3(H3), C4(H4A), C5(H5A), C6(H6A), C8(H8), C9(H9),
 C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18), N11(HN11),
 N12(HN12), N13(HN13), C23(H23), C24(H24), C25(H25), C26(H26), C29(H29),
 C30(H30), C31(H31), C32(H32), C35(H35), C36(H36), C37(H37), C38(H38), N18(HN8),
  N19(HN19), N20(HN20), C43(H43), C44(H44), C45(H45), C46(H46), C49(H49),
 C50(H50), C51(H51), C52(H52), C55(H55), C56(H56), C57(H57), C58(H58)
5.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C40(H40A,H40B,H40C), C60(H60A,H60B,H60C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.19987(10) 0.39445(10) 0.64875(3) 0.0383(3) Uani 1 1 d . . . . .
Bi2 Bi 0.20273(10) 0.27516(10) 0.77367(3) 0.0352(3) Uani 1 1 d . . . . .
Bi3 Bi 0.15535(10) 0.16436(10) 0.89997(3) 0.0329(2) Uani 1 1 d . . . . .
Bi4 Bi -0.21642(9) -0.11086(9) 0.92960(3) 0.0318(2) Uani 1 1 d . . . . .
Bi5 Bi -0.19201(10) 0.01560(9) 0.80365(3) 0.0319(2) Uani 1 1 d . . . . .
Bi6 Bi -0.17437(10) 0.13055(10) 0.68176(3) 0.0366(3) Uani 1 1 d . . . . .
I1 I 0.35603(19) 0.3342(2) 0.59097(6) 0.0464(5) Uani 1 1 d . . . . .
I2 I 0.0462(2) 0.4933(2) 0.59765(8) 0.0605(6) Uani 1 1 d . . . . .
I3 I 0.3795(2) 0.6202(2) 0.67291(8) 0.0515(5) Uani 1 1 d . . . . .
I4 I 0.03321(18) 0.39560(18) 0.72057(6) 0.0377(4) Uani 1 1 d . . . . .
I5 I 0.35079(19) 0.2458(2) 0.70887(6) 0.0442(5) Uani 1 1 d . . . . .
I6 I 0.3729(2) 0.50007(19) 0.80223(7) 0.0490(5) Uani 1 1 d . . . . .
I7 I 0.31914(17) 0.12824(17) 0.82595(6) 0.0357(4) Uani 1 1 d . . . . .
I8 I 0.00753(17) 0.28463(16) 0.83582(6) 0.0337(4) Uani 1 1 d . . . . .
I9 I 0.31048(18) 0.40391(18) 0.92532(6) 0.0397(4) Uani 1 1 d . . . . .
I10 I -0.02257(17) 0.16693(17) 0.95681(6) 0.0373(4) Uani 1 1 d . . . . .
I11 I 0.29359(18) 0.03760(18) 0.94780(6) 0.0394(4) Uani 1 1 d . . . . .
I12 I -0.37550(18) -0.05726(18) 0.98447(6) 0.0389(4) Uani 1 1 d . . . . .
I13 I -0.06187(18) -0.22688(18) 0.97630(6) 0.0407(5) Uani 1 1 d . . . . .
I14 I -0.37696(18) -0.33717(17) 0.89704(6) 0.0379(4) Uani 1 1 d . . . . .
I15 I -0.33917(17) 0.04528(17) 0.86934(6) 0.0345(4) Uani 1 1 d . . . . .
I16 I -0.02716(17) -0.09898(16) 0.85932(6) 0.0331(4) Uani 1 1 d . . . . .
I17 I -0.35767(19) -0.21594(18) 0.77827(6) 0.0400(5) Uani 1 1 d . . . . .
I18 I -0.00764(17) 0.00717(17) 0.74076(6) 0.0342(4) Uani 1 1 d . . . . .
I19 I -0.32551(18) 0.16018(17) 0.75601(6) 0.0380(4) Uani 1 1 d . . . . .
I20 I -0.3362(2) -0.10499(19) 0.65729(6) 0.0459(5) Uani 1 1 d . . . . .
I21 I 0.00550(18) 0.11355(19) 0.62554(6) 0.0425(5) Uani 1 1 d . . . . .
I22 I -0.3147(2) 0.2632(2) 0.63785(7) 0.0537(5) Uani 1 1 d . . . . .
Bi7 Bi -0.03105(10) 0.14772(10) 0.34994(3) 0.0383(3) Uani 1 1 d . . . . .
Bi8 Bi 0.41962(9) 0.64003(9) 0.06975(3) 0.0322(2) Uani 1 1 d . . . . .
Bi9 Bi 0.04537(10) 0.36502(9) 0.09831(3) 0.0324(2) Uani 1 1 d . . . . .
Bi10 Bi -0.00425(10) 0.25503(10) 0.22364(3) 0.0333(2) Uani 1 1 d . . . . .
Bi11 Bi 0.38683(10) 0.51992(9) 0.19563(3) 0.0319(2) Uani 1 1 d . . . . .
Bi12 Bi 0.35281(10) 0.40962(10) 0.31767(3) 0.0372(3) Uani 1 1 d . . . . .
I32 I -0.1952(2) -0.0802(2) 0.31949(7) 0.0498(5) Uani 1 1 d . . . . .
I33 I 0.1169(2) 0.0536(2) 0.40474(7) 0.0570(6) Uani 1 1 d . . . . .
I34 I -0.2003(2) 0.1916(2) 0.40233(7) 0.0575(6) Uani 1 1 d . . . . .
I35 I 0.15738(17) 0.14237(17) 0.27999(6) 0.0369(4) Uani 1 1 d . . . . .
I36 I -0.16518(18) 0.29059(18) 0.28428(6) 0.0387(4) Uani 1 1 d . . . . .
I37 I -0.1732(2) 0.03009(19) 0.19439(7) 0.0458(5) Uani 1 1 d . . . . .
I38 I 0.19349(17) 0.24656(17) 0.16324(5) 0.0335(4) Uani 1 1 d . . . . .
I39 I -0.11763(17) 0.40435(17) 0.17085(6) 0.0363(4) Uani 1 1 d . . . . .
I40 I -0.09359(18) 0.49210(18) 0.05115(6) 0.0385(4) Uani 1 1 d . . . . .
I41 I 0.22618(17) 0.36206(18) 0.04185(6) 0.0378(4) Uani 1 1 d . . . . .
I42 I -0.10996(18) 0.12614(17) 0.07280(6) 0.0392(4) Uani 1 1 d . . . . .
I43 I 0.58048(18) 0.86685(17) 0.10208(6) 0.0378(4) Uani 1 1 d . . . . .
I44 I 0.57928(18) 0.58585(18) 0.01535(6) 0.0393(4) Uani 1 1 d . . . . .
I45 I 0.26520(18) 0.75628(19) 0.02361(6) 0.0414(5) Uani 1 1 d . . . . .
I46 I 0.53909(18) 0.48423(17) 0.13211(6) 0.0355(4) Uani 1 1 d . . . . .
I47 I 0.22586(17) 0.62960(17) 0.13857(6) 0.0334(4) Uani 1 1 d . . . . .
I48 I 0.54621(19) 0.75534(18) 0.21958(6) 0.0401(5) Uani 1 1 d . . . . .
I49 I 0.51434(18) 0.37704(18) 0.24663(6) 0.0394(5) Uani 1 1 d . . . . .
I50 I 0.19497(17) 0.52913(17) 0.25621(6) 0.0347(4) Uani 1 1 d . . . . .
I51 I 0.51864(19) 0.64753(19) 0.33579(6) 0.0437(5) Uani 1 1 d . . . . .
I52 I 0.17005(18) 0.43542(18) 0.37281(6) 0.0414(5) Uani 1 1 d . . . . .
I53 I 0.4837(2) 0.2843(2) 0.36883(7) 0.0534(6) Uani 1 1 d . . . . .
I23 I 0.8247(2) 0.71262(19) 0.56236(7) 0.0553(5) Uani 1 1 d . . . . .
I24 I 0.60738(18) 0.55519(18) 0.57847(6) 0.0474(4) Uani 1 1 d . . . . .
I25 I 1.1922(2) 1.0636(2) 0.53438(7) 0.0584(5) Uani 1 1 d . . . . .
I26 I 1.08793(19) 0.8293(2) 0.50408(6) 0.0540(5) Uani 1 1 d . . . . .
I27 I 0.9888(2) 0.5518(2) 0.46909(7) 0.0555(5) Uani 1 1 d . . . . .
I28 I 0.74918(19) 0.39598(18) 0.48817(6) 0.0488(4) Uani 1 1 d . . . . .
I29 I 0.5208(2) 0.2264(2) 0.50518(7) 0.0566(5) Uani 1 1 d . . . . .
I30 I 0.41968(19) -0.02240(19) 0.45094(6) 0.0506(5) Uani 1 1 d . . . . .
I31 I 0.3071(2) -0.2446(2) 0.41313(6) 0.0534(5) Uani 1 1 d . . . . .
N1 N 0.979(2) 0.618(2) 0.8102(8) 0.042(6) Uani 1 1 d . . . . .
N2 N 0.943(2) 0.549(2) 0.8734(8) 0.045(6) Uani 1 1 d . . . . .
N3 N 0.782(2) 0.485(2) 0.8226(8) 0.040(6) Uani 1 1 d . . . . .
N4 N 1.181(2) 0.669(2) 0.8979(7) 0.041(6) Uani 1 1 d . . . . .
HN4 H 1.129496 0.620520 0.912278 0.049 Uiso 1 1 calc R U . . .
N5 N 0.894(2) 0.636(2) 0.7381(7) 0.039(5) Uani 1 1 d . . . . .
HN5 H 0.969832 0.671203 0.747530 0.046 Uiso 1 1 calc R U . . .
N6 N 0.807(2) 0.416(2) 0.9227(7) 0.034(5) Uani 1 1 d . . . . .
HN6 H 0.885034 0.457900 0.927943 0.041 Uiso 1 1 calc R U . . .
C1 C 1.013(3) 0.609(3) 0.8475(9) 0.041(7) Uani 1 1 d . . . . .
C2 C 1.142(3) 0.677(3) 0.8598(10) 0.046(8) Uani 1 1 d . . . . .
C3 C 1.291(3) 0.730(3) 0.9135(10) 0.049(8) Uani 1 1 d . . . . .
H3 H 1.312430 0.725598 0.940094 0.059 Uiso 1 1 calc R U . . .
C4 C 1.373(2) 0.797(3) 0.8913(9) 0.041(7) Uani 1 1 d . . . . .
H4A H 1.453063 0.837277 0.902517 0.049 Uiso 1 1 calc R U . . .
C5 C 1.345(3) 0.811(3) 0.8531(9) 0.042(7) Uani 1 1 d . . . . .
H5A H 1.402219 0.860682 0.837789 0.051 Uiso 1 1 calc R U . . .
C6 C 1.221(3) 0.744(3) 0.8379(10) 0.042(7) Uani 1 1 d . . . . .
H6A H 1.196705 0.748203 0.811449 0.050 Uiso 1 1 calc R U . . .
C7 C 0.863(3) 0.555(3) 0.8011(8) 0.039(7) Uani 1 1 d . . . . .
C8 C 0.856(4) 0.653(5) 0.7025(13) 0.087(15) Uani 1 1 d . . . . .
H8 H 0.911031 0.710799 0.688741 0.105 Uiso 1 1 calc R U . . .
C9 C 0.748(3) 0.596(3) 0.6847(9) 0.049(8) Uani 1 1 d . . . . .
H9 H 0.728374 0.607137 0.658439 0.059 Uiso 1 1 calc R U . . .
C10 C 0.656(3) 0.510(3) 0.7079(9) 0.048(8) Uani 1 1 d . . . . .
H10 H 0.574274 0.467529 0.697823 0.058 Uiso 1 1 calc R U . . .
C11 C 0.699(3) 0.501(3) 0.7432(9) 0.039(7) Uani 1 1 d . . . . .
H11 H 0.646909 0.446892 0.758907 0.046 Uiso 1 1 calc R U . . .
C12 C 0.815(3) 0.564(2) 0.7592(9) 0.039(7) Uani 1 1 d . . . . .
C13 C 0.830(2) 0.490(2) 0.8598(8) 0.035(6) Uani 1 1 d . . . . .
C14 C 0.755(3) 0.417(2) 0.8866(10) 0.041(7) Uani 1 1 d . . . . .
C15 C 0.751(3) 0.358(3) 0.9493(10) 0.054(9) Uani 1 1 d . . . . .
H15 H 0.793787 0.362013 0.973929 0.065 Uiso 1 1 calc R U . . .
C16 C 0.627(2) 0.287(3) 0.9434(10) 0.042(7) Uani 1 1 d . . . . .
H16 H 0.585006 0.240997 0.962981 0.050 Uiso 1 1 calc R U . . .
C17 C 0.570(3) 0.289(3) 0.9069(9) 0.045(7) Uani 1 1 d . . . . .
H17 H 0.485536 0.247134 0.901678 0.054 Uiso 1 1 calc R U . . .
C18 C 0.631(2) 0.348(2) 0.8789(9) 0.038(6) Uani 1 1 d . . . . .
H18 H 0.591483 0.344324 0.853778 0.045 Uiso 1 1 calc R U . . .
N7 N 0.145(3) 0.767(3) 0.7384(10) 0.067(9) Uani 1 1 d . . . . .
C19 C 0.245(3) 0.828(3) 0.7357(8) 0.043(7) Uani 1 1 d . . . . .
C20 C 0.367(4) 0.908(3) 0.7337(12) 0.070(11) Uani 1 1 d . . . . .
H20A H 0.415347 0.866795 0.718805 0.105 Uiso 1 1 calc R U . . .
H20B H 0.407451 0.930065 0.759833 0.105 Uiso 1 1 calc R U . . .
H20C H 0.361973 0.981290 0.721248 0.105 Uiso 1 1 calc R U . . .
N8 N 0.417(2) 0.040(2) 0.1796(7) 0.040(6) Uani 1 1 d . . . . .
N9 N 0.2217(19) -0.078(2) 0.1930(7) 0.036(5) Uani 1 1 d . . . . .
N10 N 0.254(2) -0.022(2) 0.1299(7) 0.040(6) Uani 1 1 d . . . . .
N11 N 0.305(2) -0.097(2) 0.2673(7) 0.040(6) Uani 1 1 d . . . . .
HN11 H 0.231398 -0.140258 0.257186 0.048 Uiso 1 1 calc R U . . .
N12 N 0.391(2) 0.109(2) 0.0799(7) 0.038(6) Uani 1 1 d D . . . .
HN12 H 0.312520 0.069087 0.075575 0.046 Uiso 1 1 calc R U . . .
N13 N 0.024(2) -0.137(2) 0.1051(7) 0.038(6) Uani 1 1 d D . . . .
HN13 H 0.078574 -0.093263 0.090588 0.046 Uiso 1 1 calc R U . . .
C21 C 0.339(2) -0.020(2) 0.2039(10) 0.041(7) Uani 1 1 d . . . . .
C22 C 0.382(3) -0.020(3) 0.2436(10) 0.045(8) Uani 1 1 d . . . . .
C23 C 0.334(3) -0.109(2) 0.3033(9) 0.037(7) Uani 1 1 d . . . . .
H23 H 0.278086 -0.162508 0.318173 0.045 Uiso 1 1 calc R U . . .
C24 C 0.453(3) -0.040(3) 0.3204(10) 0.047(8) Uani 1 1 d . . . . .
H24 H 0.478018 -0.047581 0.346516 0.056 Uiso 1 1 calc R U . . .
C25 C 0.527(2) 0.034(2) 0.2995(9) 0.039(7) Uani 1 1 d . . . . .
H25 H 0.603907 0.082175 0.311267 0.046 Uiso 1 1 calc R U . . .
C26 C 0.498(3) 0.047(2) 0.2594(9) 0.042(7) Uani 1 1 d . . . . .
H26 H 0.555270 0.098459 0.244482 0.051 Uiso 1 1 calc R U . . .
C27 C 0.371(2) 0.039(2) 0.1437(9) 0.035(6) Uani 1 1 d . . . . .
C28 C 0.450(2) 0.112(3) 0.1143(9) 0.041(7) Uani 1 1 d . . . . .
C29 C 0.456(3) 0.169(3) 0.0508(9) 0.051(9) Uani 1 1 d . . . . .
H29 H 0.415464 0.165392 0.025790 0.061 Uiso 1 1 calc R U . . .
C30 C 0.574(3) 0.232(3) 0.0576(10) 0.055(10) Uani 1 1 d . . . . .
H30 H 0.617369 0.272227 0.037452 0.067 Uiso 1 1 calc R U . . .
C31 C 0.633(2) 0.238(3) 0.0942(9) 0.047(8) Uani 1 1 d . . . . .
H31 H 0.715542 0.286105 0.099759 0.056 Uiso 1 1 calc R U . . .
C32 C 0.566(3) 0.171(3) 0.1233(8) 0.040(6) Uani 1 1 d . . . . .
H32 H 0.604041 0.170185 0.148381 0.048 Uiso 1 1 calc R U . . .
C33 C 0.188(2) -0.082(2) 0.1572(10) 0.043(8) Uani 1 1 d . . . . .
C34 C 0.060(3) -0.142(3) 0.1410(9) 0.040(7) Uani 1 1 d . . . . .
C35 C -0.087(3) -0.193(3) 0.0885(11) 0.052(8) Uani 1 1 d . . . . .
H35 H -0.108624 -0.180505 0.062394 0.062 Uiso 1 1 calc R U . . .
C36 C -0.173(3) -0.270(3) 0.1103(11) 0.050(9) Uani 1 1 d . . . . .
H36 H -0.251393 -0.314948 0.098511 0.060 Uiso 1 1 calc R U . . .
C37 C -0.143(3) -0.280(3) 0.1495(9) 0.041(7) Uani 1 1 d . . . . .
H37 H -0.200895 -0.330774 0.164466 0.049 Uiso 1 1 calc R U . . .
C38 C -0.027(3) -0.214(3) 0.1663(10) 0.049(8) Uani 1 1 d . . . . .
H38 H -0.005214 -0.216465 0.192994 0.059 Uiso 1 1 calc R U . . .
N14 N 1.050(2) 0.774(2) 0.2672(9) 0.048(7) Uani 1 1 d . . . . .
C39 C 0.957(4) 0.719(3) 0.2640(9) 0.053(9) Uani 1 1 d . . . . .
C40 C 0.827(2) 0.634(3) 0.2592(9) 0.041(7) Uani 1 1 d . . . . .
H40A H 0.775858 0.667913 0.241686 0.062 Uiso 1 1 calc R U . . .
H40B H 0.792933 0.624871 0.284290 0.062 Uiso 1 1 calc R U . . .
H40C H 0.828967 0.554810 0.248444 0.062 Uiso 1 1 calc R U . . .
N15 N 0.589(3) 0.759(3) 0.4905(8) 0.059(8) Uani 1 1 d . . . . .
N16 N 0.756(3) 0.805(3) 0.4510(10) 0.070(9) Uani 1 1 d . . . . .
N17 N 0.618(3) 0.616(3) 0.4412(9) 0.069(8) Uani 1 1 d . . . . .
N18 N 0.674(3) 0.965(3) 0.5293(10) 0.074(8) Uani 1 1 d . U . . .
HN8 H 0.606573 0.907540 0.533450 0.089 Uiso 1 1 calc R U . . .
N19 N 0.381(3) 0.604(3) 0.5046(10) 0.067(8) Uani 1 1 d . U . . .
HN19 H 0.410470 0.676708 0.515845 0.081 Uiso 1 1 calc R U . . .
N20 N 0.762(3) 0.549(3) 0.3885(9) 0.070(8) Uani 1 1 d . U . . .
HN20 H 0.700218 0.494484 0.397306 0.084 Uiso 1 1 calc R U . . .
C41 C 0.694(3) 0.831(2) 0.4800(10) 0.059(9) Uani 1 1 d . . . . .
C42 C 0.742(3) 0.944(4) 0.4991(12) 0.069(11) Uani 1 1 d . . . . .
C43 C 0.708(4) 1.076(3) 0.5542(12) 0.074(9) Uani 1 1 d . U . . .
H43 H 0.659658 1.087564 0.574440 0.089 Uiso 1 1 calc R U . . .
C44 C 0.803(4) 1.153(4) 0.5475(12) 0.081(13) Uani 1 1 d . . . . .
H44 H 0.826222 1.224995 0.563939 0.097 Uiso 1 1 calc R U . . .
C45 C 0.884(3) 1.147(3) 0.5172(11) 0.058(9) Uani 1 1 d . . . . .
H45 H 0.956371 1.210809 0.513755 0.069 Uiso 1 1 calc R U . . .
C46 C 0.845(3) 1.036(4) 0.4929(11) 0.066(9) Uani 1 1 d . . . . .
H46 H 0.891682 1.026164 0.472122 0.079 Uiso 1 1 calc R U . . .
C47 C 0.551(3) 0.646(3) 0.4674(8) 0.051(8) Uani 1 1 d . . . . .
C48 C 0.443(3) 0.567(2) 0.4766(11) 0.059(10) Uani 1 1 d . . . . .
C49 C 0.281(4) 0.534(4) 0.5147(13) 0.087(10) Uani 1 1 d . U . . .
H49 H 0.237313 0.567363 0.532417 0.104 Uiso 1 1 calc R U . . .
C50 C 0.238(5) 0.430(4) 0.5034(14) 0.093(11) Uani 1 1 d . U . . .
H50 H 0.170574 0.380769 0.515633 0.111 Uiso 1 1 calc R U . . .
C51 C 0.282(4) 0.379(4) 0.4735(13) 0.083(11) Uani 1 1 d . U . . .
H51 H 0.241333 0.299361 0.462548 0.100 Uiso 1 1 calc R U . . .
C52 C 0.401(4) 0.456(3) 0.4588(12) 0.079(11) Uani 1 1 d . U . . .
H52 H 0.441413 0.427931 0.438930 0.095 Uiso 1 1 calc R U . . .
C53 C 0.717(3) 0.693(3) 0.4346(8) 0.038(6) Uani 1 1 d . . . . .
C54 C 0.790(2) 0.667(2) 0.4060(8) 0.037(6) Uani 1 1 d . . . . .
C55 C 0.813(4) 0.511(3) 0.3627(9) 0.058(7) Uani 1 1 d . U . . .
H55 H 0.777216 0.432105 0.350504 0.070 Uiso 1 1 calc R U . . .
C56 C 0.921(4) 0.583(3) 0.3520(10) 0.068(8) Uani 1 1 d . U . . .
H56 H 0.966125 0.552393 0.333967 0.081 Uiso 1 1 calc R U . . .
C57 C 0.964(4) 0.699(4) 0.3673(12) 0.074(10) Uani 1 1 d . U . . .
H57 H 1.038527 0.750086 0.359418 0.089 Uiso 1 1 calc R U . . .
C58 C 0.899(3) 0.744(3) 0.3954(11) 0.064(8) Uani 1 1 d . U . . .
H58 H 0.929662 0.824790 0.406445 0.077 Uiso 1 1 calc R U . . .
N21 N 0.430(3) 0.837(3) 0.5594(11) 0.076(10) Uani 1 1 d . U . . .
C59 C 0.368(5) 0.870(4) 0.5835(15) 0.093(14) Uani 1 1 d . U . . .
C60 C 0.285(6) 0.867(6) 0.6128(16) 0.14(2) Uani 1 1 d . U . . .
H60A H 0.317715 0.839656 0.636470 0.211 Uiso 1 1 calc R U . . .
H60B H 0.204536 0.810400 0.604175 0.211 Uiso 1 1 calc R U . . .
H60C H 0.276024 0.948092 0.617753 0.211 Uiso 1 1 calc R U . . .
O1 O 1.0584(17) 0.516(2) 0.9547(6) 0.044(5) Uani 1 1 d D . . . .
H1O1 H 1.07(3) 0.579(12) 0.969(5) 0.052 Uiso 1 1 d D U . . .
H2O1 H 1.08(2) 0.467(16) 0.968(6) 0.052 Uiso 1 1 d D U . . .
O2 O 0.148(2) 0.0103(18) 0.0468(6) 0.052(6) Uani 1 1 d D . . . .
H1O2 H 0.125(9) 0.068(4) 0.056(6) 0.062 Uiso 1 1 d D U . . .
H2O2 H 0.122(8) 0.000(17) 0.0235(10) 0.062 Uiso 1 1 d D U . . .


_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 2.961(2) . ?
Bi1 I2 2.891(2) . ?
Bi1 I3 2.870(3) . ?
Bi1 I4 3.245(2) . ?
Bi1 I5 3.419(2) . ?
Bi1 I21 3.394(2) . ?
Bi2 I4 3.204(2) . ?
Bi2 I5 2.973(2) . ?
Bi2 I6 2.855(3) . ?
Bi2 I7 3.016(2) . ?
Bi2 I8 3.226(2) . ?
Bi2 I18 3.427(2) . ?
Bi3 I7 3.364(2) . ?
Bi3 I8 3.281(2) . ?
Bi3 I9 2.890(2) . ?
Bi3 I10 2.932(2) . ?
Bi3 I11 2.914(2) . ?
Bi3 I16 3.350(2) . ?
Bi4 I10 3.390(2) . ?
Bi4 I12 2.885(2) . ?
Bi4 I13 2.934(2) . ?
Bi4 I14 2.866(2) . ?
Bi4 I15 3.299(2) . ?
Bi4 I16 3.352(2) . ?
Bi5 I8 3.379(2) . ?
Bi5 I15 2.992(2) . ?
Bi5 I16 3.178(2) . ?
Bi5 I17 2.863(2) . ?
Bi5 I18 3.153(2) . ?
Bi5 I19 3.019(2) . ?
Bi6 I18 3.322(2) . ?
Bi6 I19 3.263(2) . ?
Bi6 I20 2.874(2) . ?
Bi6 I21 2.968(2) . ?
Bi6 I22 2.903(2) . ?
Bi7 I32 2.872(3) . ?
Bi7 I33 2.896(2) . ?
Bi7 I34 2.873(2) . ?
Bi7 I35 3.365(2) . ?
Bi7 I36 3.389(2) . ?
Bi8 I41 3.394(2) . ?
Bi8 I43 2.869(2) . ?
Bi8 I44 2.881(2) . ?
Bi8 I45 2.924(2) . ?
Bi8 I46 3.324(2) . ?
Bi8 I47 3.350(2) . ?
Bi9 I38 3.289(2) . ?
Bi9 I39 3.327(2) . ?
Bi9 I40 2.909(2) . ?
Bi9 I41 2.948(2) . ?
Bi9 I42 2.886(2) . ?
Bi9 I47 3.348(2) . ?
Bi10 I35 3.154(2) . ?
Bi10 I36 2.979(2) . ?
Bi10 I37 2.856(2) . ?
Bi10 I38 3.203(2) . ?
Bi10 I39 3.027(2) . ?
Bi10 I50 3.423(2) . ?
Bi11 I38 3.391(2) . ?
Bi11 I46 2.988(2) . ?
Bi11 I47 3.144(2) . ?
Bi11 I48 2.859(2) . ?
Bi11 I49 3.029(2) . ?
Bi11 I50 3.158(2) . ?
Bi12 I35 3.400(2) . ?
Bi12 I49 3.254(2) . ?
Bi12 I50 3.284(2) . ?
Bi12 I51 2.872(2) . ?
Bi12 I52 2.992(2) . ?
Bi12 I53 2.918(2) . ?
I23 I24 2.729(3) . ?
I25 I26 2.758(3) . ?
I26 I27 3.232(3) . ?
I27 I28 2.943(3) . ?
I28 I29 2.889(3) . ?
I29 I30 3.246(3) . ?
I30 I31 2.754(3) . ?
N1 C1 1.35(4) . ?
N1 C7 1.32(4) . ?
N2 C1 1.33(4) . ?
N2 C13 1.32(3) . ?
N3 C7 1.33(4) . ?
N3 C13 1.37(4) . ?
N4 HN4 0.8800 . ?
N4 C2 1.39(4) . ?
N4 C3 1.32(4) . ?
N5 HN5 0.8800 . ?
N5 C8 1.33(5) . ?
N5 C12 1.32(3) . ?
N6 HN6 0.8800 . ?
N6 C14 1.35(4) . ?
N6 C15 1.27(4) . ?
C1 C2 1.47(4) . ?
C2 C6 1.32(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.34(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.37(4) . ?
C5 H5A 0.9500 . ?
C5 C6 1.45(4) . ?
C6 H6A 0.9500 . ?
C7 C12 1.54(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.31(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.52(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.31(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.38(4) . ?
C13 C14 1.44(4) . ?
C14 C18 1.41(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.41(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.39(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.33(4) . ?
C18 H18 0.9500 . ?
N7 C19 1.16(4) . ?
C19 C20 1.44(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N8 C21 1.33(3) . ?
N8 C27 1.32(4) . ?
N9 C21 1.33(3) . ?
N9 C33 1.27(4) . ?
N10 C27 1.36(3) . ?
N10 C33 1.34(4) . ?
N11 HN11 0.8800 . ?
N11 C22 1.40(4) . ?
N11 C23 1.30(4) . ?
N12 HN12 0.8800 . ?
N12 C28 1.33(4) . ?
N12 C29 1.38(4) . ?
N13 HN13 0.8800 . ?
N13 C34 1.30(4) . ?
N13 C35 1.33(4) . ?
C21 C22 1.44(5) . ?
C22 C26 1.38(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.44(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.30(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.43(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.52(4) . ?
C28 C32 1.32(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.33(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.39(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.43(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.49(4) . ?
C34 C38 1.47(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.41(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.40(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.39(4) . ?
C38 H38 0.9500 . ?
N14 C39 1.07(4) . ?
C39 C40 1.51(5) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
N15 C41 1.33(4) . ?
N15 C47 1.43(5) . ?
N16 C41 1.35(5) . ?
N16 C53 1.33(4) . ?
N17 C47 1.32(4) . ?
N17 C53 1.26(4) . ?
N18 HN8 0.8800 . ?
N18 C42 1.40(5) . ?
N18 C43 1.46(5) . ?
N19 HN19 0.8800 . ?
N19 C48 1.36(5) . ?
N19 C49 1.27(5) . ?
N20 HN20 0.8800 . ?
N20 C54 1.41(4) . ?
N20 C55 1.23(4) . ?
C41 C42 1.39(5) . ?
C42 C46 1.37(5) . ?
C43 H43 0.9500 . ?
C43 C44 1.24(5) . ?
C44 H44 0.9500 . ?
C44 C45 1.46(6) . ?
C45 H45 0.9500 . ?
C45 C46 1.45(5) . ?
C46 H46 0.9500 . ?
C47 C48 1.38(5) . ?
C48 C52 1.35(5) . ?
C49 H49 0.9500 . ?
C49 C50 1.21(6) . ?
C50 H50 0.9500 . ?
C50 C51 1.37(6) . ?
C51 H51 0.9500 . ?
C51 C52 1.53(6) . ?
C52 H52 0.9500 . ?
C53 C54 1.41(4) . ?
C54 C58 1.39(4) . ?
C55 H55 0.9500 . ?
C55 C56 1.36(5) . ?
C56 H56 0.9500 . ?
C56 C57 1.36(5) . ?
C57 H57 0.9500 . ?
C57 C58 1.44(5) . ?
C58 H58 0.9500 . ?
N21 C59 1.24(6) . ?
C59 C60 1.43(8) . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
O1 H1O1 0.840(15) . ?
O1 H2O1 0.840(14) . ?
O2 H1O2 0.839(14) . ?
O2 H2O2 0.838(14) . ?

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 I4 165.35(7) . . ?
I1 Bi1 I5 83.77(6) . . ?
I1 Bi1 I21 86.22(6) . . ?
I2 Bi1 I1 97.98(8) . . ?
I2 Bi1 I4 93.49(7) . . ?
I2 Bi1 I5 172.82(8) . . ?
I2 Bi1 I21 88.96(7) . . ?
I3 Bi1 I1 92.54(7) . . ?
I3 Bi1 I2 96.84(8) . . ?
I3 Bi1 I4 95.13(7) . . ?
I3 Bi1 I5 90.02(7) . . ?
I3 Bi1 I21 174.18(7) . . ?
I4 Bi1 I5 83.77(5) . . ?
I4 Bi1 I21 84.89(6) . . ?
I21 Bi1 I5 84.20(6) . . ?
I4 Bi2 I8 83.17(5) . . ?
I4 Bi2 I18 84.29(6) . . ?
I5 Bi2 I4 92.12(6) . . ?
I5 Bi2 I7 93.36(6) . . ?
I5 Bi2 I8 171.59(7) . . ?
I5 Bi2 I18 88.13(6) . . ?
I6 Bi2 I4 95.11(7) . . ?
I6 Bi2 I5 93.35(7) . . ?
I6 Bi2 I7 93.36(7) . . ?
I6 Bi2 I8 94.00(7) . . ?
I6 Bi2 I18 178.42(7) . . ?
I7 Bi2 I4 169.63(7) . . ?
I7 Bi2 I8 90.28(6) . . ?
I7 Bi2 I18 87.09(6) . . ?
I8 Bi2 I18 84.48(5) . . ?
I8 Bi3 I7 83.54(5) . . ?
I8 Bi3 I16 83.95(5) . . ?
I9 Bi3 I7 95.33(6) . . ?
I9 Bi3 I8 89.62(6) . . ?
I9 Bi3 I10 93.38(6) . . ?
I9 Bi3 I11 94.80(7) . . ?
I9 Bi3 I16 172.57(7) . . ?
I10 Bi3 I7 170.31(7) . . ?
I10 Bi3 I8 92.29(6) . . ?
I10 Bi3 I16 90.59(6) . . ?
I11 Bi3 I7 89.30(6) . . ?
I11 Bi3 I8 171.91(7) . . ?
I11 Bi3 I10 94.21(7) . . ?
I11 Bi3 I16 91.17(6) . . ?
I16 Bi3 I7 80.29(5) . . ?
I12 Bi4 I10 86.32(6) . . ?
I12 Bi4 I13 102.51(7) . . ?
I12 Bi4 I15 86.36(6) . . ?
I12 Bi4 I16 164.91(6) . . ?
I13 Bi4 I10 90.74(6) . . ?
I13 Bi4 I15 168.63(7) . . ?
I13 Bi4 I16 88.47(6) . . ?
I14 Bi4 I10 172.95(7) . . ?
I14 Bi4 I12 98.19(7) . . ?
I14 Bi4 I13 93.55(7) . . ?
I14 Bi4 I15 92.19(6) . . ?
I14 Bi4 I16 91.34(6) . . ?
I15 Bi4 I10 82.65(6) . . ?
I15 Bi4 I16 81.58(5) . . ?
I16 Bi4 I10 83.17(5) . . ?
I15 Bi5 I8 86.80(6) . . ?
I15 Bi5 I16 89.50(6) . . ?
I15 Bi5 I18 172.62(7) . . ?
I15 Bi5 I19 89.04(6) . . ?
I16 Bi5 I8 85.08(6) . . ?
I17 Bi5 I8 178.18(7) . . ?
I17 Bi5 I15 92.85(6) . . ?
I17 Bi5 I16 93.14(6) . . ?
I17 Bi5 I18 93.84(6) . . ?
I17 Bi5 I19 95.26(7) . . ?
I18 Bi5 I8 86.42(6) . . ?
I18 Bi5 I16 87.02(5) . . ?
I19 Bi5 I8 86.52(6) . . ?
I19 Bi5 I16 171.54(7) . . ?
I19 Bi5 I18 93.45(6) . . ?
I19 Bi6 I18 86.07(5) . . ?
I20 Bi6 I18 90.80(6) . . ?
I20 Bi6 I19 93.70(6) . . ?
I20 Bi6 I21 92.90(7) . . ?
I20 Bi6 I22 95.02(7) . . ?
I21 Bi6 I18 84.70(6) . . ?
I21 Bi6 I19 168.72(7) . . ?
I22 Bi6 I18 172.64(8) . . ?
I22 Bi6 I19 89.06(7) . . ?
I22 Bi6 I21 99.46(7) . . ?
Bi2 I4 Bi1 91.48(6) . . ?
Bi2 I5 Bi1 92.25(6) . . ?
Bi2 I7 Bi3 93.60(6) . . ?
Bi2 I8 Bi3 91.39(5) . . ?
Bi2 I8 Bi5 94.32(6) . . ?
Bi3 I8 Bi5 93.93(5) . . ?
Bi3 I10 Bi4 96.26(6) . . ?
Bi5 I15 Bi4 96.05(5) . . ?
Bi3 I16 Bi4 89.48(5) . . ?
Bi5 I16 Bi3 96.41(5) . . ?
Bi5 I16 Bi4 91.57(5) . . ?
Bi5 I18 Bi2 94.73(6) . . ?
Bi5 I18 Bi6 88.04(5) . . ?
Bi6 I18 Bi2 95.77(5) . . ?
Bi5 I19 Bi6 91.45(6) . . ?
Bi6 I21 Bi1 95.62(7) . . ?
I32 Bi7 I33 97.80(7) . . ?
I32 Bi7 I34 93.75(8) . . ?
I32 Bi7 I35 90.55(7) . . ?
I32 Bi7 I36 89.28(7) . . ?
I33 Bi7 I35 92.42(7) . . ?
I33 Bi7 I36 171.50(7) . . ?
I34 Bi7 I33 97.13(8) . . ?
I34 Bi7 I35 168.89(7) . . ?
I34 Bi7 I36 87.04(6) . . ?
I35 Bi7 I36 82.77(5) . . ?
I43 Bi8 I41 173.53(7) . . ?
I43 Bi8 I44 98.02(7) . . ?
I43 Bi8 I45 93.28(7) . . ?
I43 Bi8 I46 92.09(6) . . ?
I43 Bi8 I47 91.87(6) . . ?
I44 Bi8 I41 85.99(6) . . ?
I44 Bi8 I45 103.20(7) . . ?
I44 Bi8 I46 87.39(6) . . ?
I44 Bi8 I47 165.33(6) . . ?
I45 Bi8 I41 90.73(6) . . ?
I45 Bi8 I46 167.32(7) . . ?
I45 Bi8 I47 86.93(6) . . ?
I46 Bi8 I41 82.98(6) . . ?
I46 Bi8 I47 81.41(5) . . ?
I47 Bi8 I41 83.27(5) . . ?
I38 Bi9 I39 83.92(5) . . ?
I38 Bi9 I47 84.04(5) . . ?
I39 Bi9 I47 79.84(5) . . ?
I40 Bi9 I38 170.90(7) . . ?
I40 Bi9 I39 87.98(6) . . ?
I40 Bi9 I41 95.28(6) . . ?
I40 Bi9 I47 90.47(6) . . ?
I41 Bi9 I38 92.03(6) . . ?
I41 Bi9 I39 169.86(7) . . ?
I41 Bi9 I47 90.52(6) . . ?
I42 Bi9 I38 90.21(6) . . ?
I42 Bi9 I39 95.75(6) . . ?
I42 Bi9 I40 94.73(7) . . ?
I42 Bi9 I41 93.55(6) . . ?
I42 Bi9 I47 173.08(6) . . ?
I35 Bi10 I38 85.19(5) . . ?
I35 Bi10 I50 85.46(6) . . ?
I36 Bi10 I35 93.40(6) . . ?
I36 Bi10 I38 172.86(7) . . ?
I36 Bi10 I39 89.73(6) . . ?
I36 Bi10 I50 87.41(6) . . ?
I37 Bi10 I35 96.35(7) . . ?
I37 Bi10 I36 93.00(7) . . ?
I37 Bi10 I38 94.12(6) . . ?
I37 Bi10 I39 93.73(7) . . ?
I37 Bi10 I50 178.12(7) . . ?
I38 Bi10 I50 85.50(5) . . ?
I39 Bi10 I35 169.27(7) . . ?
I39 Bi10 I38 90.44(6) . . ?
I39 Bi10 I50 84.43(6) . . ?
I46 Bi11 I38 85.52(6) . . ?
I46 Bi11 I47 90.40(6) . . ?
I46 Bi11 I49 89.32(6) . . ?
I46 Bi11 I50 171.84(7) . . ?
I47 Bi11 I38 85.59(6) . . ?
I47 Bi11 I50 86.43(6) . . ?
I48 Bi11 I38 177.18(7) . . ?
I48 Bi11 I46 93.51(6) . . ?
I48 Bi11 I47 91.77(6) . . ?
I48 Bi11 I49 97.00(7) . . ?
I48 Bi11 I50 94.09(6) . . ?
I49 Bi11 I38 85.64(6) . . ?
I49 Bi11 I47 171.23(7) . . ?
I49 Bi11 I50 92.66(6) . . ?
I50 Bi11 I38 86.74(5) . . ?
I49 Bi12 I35 83.94(6) . . ?
I49 Bi12 I50 86.42(5) . . ?
I50 Bi12 I35 83.86(5) . . ?
I51 Bi12 I35 169.95(7) . . ?
I51 Bi12 I49 89.03(6) . . ?
I51 Bi12 I50 88.55(6) . . ?
I51 Bi12 I52 95.38(7) . . ?
I51 Bi12 I53 95.86(7) . . ?
I52 Bi12 I35 90.55(6) . . ?
I52 Bi12 I49 170.45(7) . . ?
I52 Bi12 I50 85.23(6) . . ?
I53 Bi12 I35 91.57(6) . . ?
I53 Bi12 I49 91.99(7) . . ?
I53 Bi12 I50 175.29(7) . . ?
I53 Bi12 I52 95.97(7) . . ?
Bi7 I35 Bi12 90.05(6) . . ?
Bi10 I35 Bi7 90.37(5) . . ?
Bi10 I35 Bi12 96.70(6) . . ?
Bi10 I36 Bi7 92.98(6) . . ?
Bi9 I38 Bi11 93.21(5) . . ?
Bi10 I38 Bi9 90.86(5) . . ?
Bi10 I38 Bi11 93.79(6) . . ?
Bi10 I39 Bi9 93.30(6) . . ?
Bi9 I41 Bi8 96.09(6) . . ?
Bi11 I46 Bi8 95.04(6) . . ?
Bi9 I47 Bi8 89.74(5) . . ?
Bi11 I47 Bi8 91.67(5) . . ?
Bi11 I47 Bi9 96.72(6) . . ?
Bi11 I49 Bi12 91.37(6) . . ?
Bi11 I50 Bi10 93.96(6) . . ?
Bi11 I50 Bi12 88.57(5) . . ?
Bi12 I50 Bi10 93.86(5) . . ?
I25 I26 I27 175.17(10) . . ?
I28 I27 I26 120.21(9) . . ?
I29 I28 I27 175.39(10) . . ?
I28 I29 I30 117.69(9) . . ?
I31 I30 I29 171.07(9) . . ?
C7 N1 C1 111(3) . . ?
C13 N2 C1 115(3) . . ?
C7 N3 C13 111(2) . . ?
C2 N4 HN4 118.7 . . ?
C3 N4 HN4 118.7 . . ?
C3 N4 C2 123(3) . . ?
C8 N5 HN5 120.7 . . ?
C12 N5 HN5 120.7 . . ?
C12 N5 C8 119(3) . . ?
C14 N6 HN6 118.1 . . ?
C15 N6 HN6 118.1 . . ?
C15 N6 C14 124(3) . . ?
N1 C1 C2 114(3) . . ?
N2 C1 N1 127(3) . . ?
N2 C1 C2 119(3) . . ?
N4 C2 C1 116(3) . . ?
C6 C2 N4 118(3) . . ?
C6 C2 C1 126(3) . . ?
N4 C3 H3 120.3 . . ?
N4 C3 C4 119(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4A 118.6 . . ?
C3 C4 C5 123(3) . . ?
C5 C4 H4A 118.6 . . ?
C4 C5 H5A 122.4 . . ?
C4 C5 C6 115(3) . . ?
C6 C5 H5A 122.4 . . ?
C2 C6 C5 122(3) . . ?
C2 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
N1 C7 N3 130(3) . . ?
N1 C7 C12 115(3) . . ?
N3 C7 C12 116(3) . . ?
N5 C8 H8 117.3 . . ?
C9 C8 N5 125(4) . . ?
C9 C8 H8 117.3 . . ?
C8 C9 H9 121.4 . . ?
C8 C9 C10 117(3) . . ?
C10 C9 H9 121.4 . . ?
C9 C10 H10 123.3 . . ?
C11 C10 C9 113(3) . . ?
C11 C10 H10 123.3 . . ?
C10 C11 H11 117.6 . . ?
C10 C11 C12 125(3) . . ?
C12 C11 H11 117.6 . . ?
N5 C12 C7 116(3) . . ?
N5 C12 C11 120(3) . . ?
C11 C12 C7 124(3) . . ?
N2 C13 N3 126(3) . . ?
N2 C13 C14 116(3) . . ?
N3 C13 C14 118(3) . . ?
N6 C14 C13 117(3) . . ?
N6 C14 C18 117(3) . . ?
C18 C14 C13 126(3) . . ?
N6 C15 H15 119.0 . . ?
N6 C15 C16 122(3) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 122.5 . . ?
C17 C16 C15 115(3) . . ?
C17 C16 H16 122.5 . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122(3) . . ?
C18 C17 H17 118.9 . . ?
C14 C18 H18 120.2 . . ?
C17 C18 C14 120(3) . . ?
C17 C18 H18 120.2 . . ?
N7 C19 C20 177(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C27 N8 C21 116(3) . . ?
C33 N9 C21 117(3) . . ?
C33 N10 C27 112(3) . . ?
C22 N11 HN11 118.1 . . ?
C23 N11 HN11 118.1 . . ?
C23 N11 C22 124(3) . . ?
C28 N12 HN12 120.5 . . ?
C28 N12 C29 119(3) . . ?
C29 N12 HN12 120.5 . . ?
C34 N13 HN13 117.5 . . ?
C34 N13 C35 125(3) . . ?
C35 N13 HN13 117.5 . . ?
N8 C21 C22 119(3) . . ?
N9 C21 N8 122(3) . . ?
N9 C21 C22 119(3) . . ?
N11 C22 C21 118(3) . . ?
C26 C22 N11 118(3) . . ?
C26 C22 C21 124(3) . . ?
N11 C23 H23 120.6 . . ?
N11 C23 C24 119(3) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 H24 120.6 . . ?
C25 C24 C23 119(3) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 118.2 . . ?
C24 C25 C26 124(3) . . ?
C26 C25 H25 118.2 . . ?
C22 C26 C25 117(3) . . ?
C22 C26 H26 121.6 . . ?
C25 C26 H26 121.6 . . ?
N8 C27 N10 125(3) . . ?
N8 C27 C28 120(2) . . ?
N10 C27 C28 115(3) . . ?
N12 C28 C27 115(2) . . ?
C32 C28 N12 124(3) . . ?
C32 C28 C27 121(3) . . ?
N12 C29 H29 119.7 . . ?
C30 C29 N12 121(3) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120(3) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.8 . . ?
C30 C31 C32 118(3) . . ?
C32 C31 H31 120.8 . . ?
C28 C32 C31 118(3) . . ?
C28 C32 H32 121.1 . . ?
C31 C32 H32 121.1 . . ?
N9 C33 N10 127(3) . . ?
N9 C33 C34 123(3) . . ?
N10 C33 C34 110(3) . . ?
N13 C34 C33 122(3) . . ?
N13 C34 C38 120(3) . . ?
C38 C34 C33 118(3) . . ?
N13 C35 H35 120.7 . . ?
N13 C35 C36 119(3) . . ?
C36 C35 H35 120.7 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 120(3) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 120.3 . . ?
C38 C37 C36 119(3) . . ?
C38 C37 H37 120.3 . . ?
C34 C38 H38 121.4 . . ?
C37 C38 C34 117(3) . . ?
C37 C38 H38 121.4 . . ?
N14 C39 C40 177(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C41 N15 C47 111(3) . . ?
C53 N16 C41 117(3) . . ?
C53 N17 C47 118(3) . . ?
C42 N18 HN8 118.3 . . ?
C42 N18 C43 123(4) . . ?
C43 N18 HN8 118.3 . . ?
C48 N19 HN19 119.2 . . ?
C49 N19 HN19 119.2 . . ?
C49 N19 C48 122(4) . . ?
C54 N20 HN20 115.5 . . ?
C55 N20 HN20 115.5 . . ?
C55 N20 C54 129(3) . . ?
N15 C41 N16 125(3) . . ?
N15 C41 C42 119(4) . . ?
N16 C41 C42 116(3) . . ?
C41 C42 N18 113(3) . . ?
C46 C42 N18 117(4) . . ?
C46 C42 C41 130(4) . . ?
N18 C43 H43 122.0 . . ?
C44 C43 N18 116(5) . . ?
C44 C43 H43 122.0 . . ?
C43 C44 H44 116.2 . . ?
C43 C44 C45 128(5) . . ?
C45 C44 H44 116.2 . . ?
C44 C45 H45 123.0 . . ?
C46 C45 C44 114(4) . . ?
C46 C45 H45 123.0 . . ?
C42 C46 C45 122(4) . . ?
C42 C46 H46 119.0 . . ?
C45 C46 H46 119.0 . . ?
N17 C47 N15 124(3) . . ?
N17 C47 C48 121(3) . . ?
C48 C47 N15 114(3) . . ?
N19 C48 C47 118(3) . . ?
C52 C48 N19 121(4) . . ?
C52 C48 C47 121(4) . . ?
N19 C49 H49 117.8 . . ?
C50 C49 N19 124(6) . . ?
C50 C49 H49 117.8 . . ?
C49 C50 H50 118.8 . . ?
C49 C50 C51 122(5) . . ?
C51 C50 H50 118.8 . . ?
C50 C51 H51 121.8 . . ?
C50 C51 C52 116(4) . . ?
C52 C51 H51 121.8 . . ?
C48 C52 C51 114(4) . . ?
C48 C52 H52 123.2 . . ?
C51 C52 H52 123.2 . . ?
N16 C53 C54 115(3) . . ?
N17 C53 N16 124(3) . . ?
N17 C53 C54 121(3) . . ?
N20 C54 C53 120(3) . . ?
C58 C54 N20 113(3) . . ?
C58 C54 C53 126(3) . . ?
N20 C55 H55 120.5 . . ?
N20 C55 C56 119(4) . . ?
C56 C55 H55 120.5 . . ?
C55 C56 H56 120.5 . . ?
C57 C56 C55 119(3) . . ?
C57 C56 H56 120.5 . . ?
C56 C57 H57 119.5 . . ?
C56 C57 C58 121(4) . . ?
C58 C57 H57 119.5 . . ?
C54 C58 C57 118(3) . . ?
C54 C58 H58 121.0 . . ?
C57 C58 H58 121.0 . . ?
N21 C59 C60 162(5) . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
H1O1 O1 H2O1 105(4) . . ?
H1O2 O2 H2O2 106(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N4 -179(2) . . . . ?
N1 C1 C2 C6 0(4) . . . . ?
N1 C7 C12 N5 -2(3) . . . . ?
N1 C7 C12 C11 177(2) . . . . ?
N2 C1 C2 N4 3(4) . . . . ?
N2 C1 C2 C6 -178(3) . . . . ?
N2 C13 C14 N6 0(4) . . . . ?
N2 C13 C14 C18 179(3) . . . . ?
N3 C7 C12 N5 179(2) . . . . ?
N3 C7 C12 C11 -3(4) . . . . ?
N3 C13 C14 N6 175(2) . . . . ?
N3 C13 C14 C18 -6(4) . . . . ?
N4 C2 C6 C5 -2(4) . . . . ?
N4 C3 C4 C5 3(4) . . . . ?
N5 C8 C9 C10 5(6) . . . . ?
N6 C14 C18 C17 2(4) . . . . ?
N6 C15 C16 C17 -2(5) . . . . ?
C1 N1 C7 N3 -2(4) . . . . ?
C1 N1 C7 C12 178(2) . . . . ?
C1 N2 C13 N3 0(4) . . . . ?
C1 N2 C13 C14 176(2) . . . . ?
C1 C2 C6 C5 178(3) . . . . ?
C2 N4 C3 C4 -4(4) . . . . ?
C3 N4 C2 C1 -177(3) . . . . ?
C3 N4 C2 C6 4(4) . . . . ?
C3 C4 C5 C6 -2(4) . . . . ?
C4 C5 C6 C2 1(4) . . . . ?
C7 N1 C1 N2 -2(4) . . . . ?
C7 N1 C1 C2 -180(2) . . . . ?
C7 N3 C13 N2 -4(4) . . . . ?
C7 N3 C13 C14 -179(2) . . . . ?
C8 N5 C12 C7 -176(3) . . . . ?
C8 N5 C12 C11 5(4) . . . . ?
C8 C9 C10 C11 -3(5) . . . . ?
C9 C10 C11 C12 2(4) . . . . ?
C10 C11 C12 N5 -4(4) . . . . ?
C10 C11 C12 C7 178(3) . . . . ?
C12 N5 C8 C9 -6(6) . . . . ?
C13 N2 C1 N1 3(4) . . . . ?
C13 N2 C1 C2 -180(3) . . . . ?
C13 N3 C7 N1 5(4) . . . . ?
C13 N3 C7 C12 -176(2) . . . . ?
C13 C14 C18 C17 -177(3) . . . . ?
C14 N6 C15 C16 1(5) . . . . ?
C15 N6 C14 C13 179(3) . . . . ?
C15 N6 C14 C18 0(4) . . . . ?
C15 C16 C17 C18 4(4) . . . . ?
C16 C17 C18 C14 -4(4) . . . . ?
N8 C21 C22 N11 -171(2) . . . . ?
N8 C21 C22 C26 5(4) . . . . ?
N8 C27 C28 N12 -176(2) . . . . ?
N8 C27 C28 C32 4(4) . . . . ?
N9 C21 C22 N11 11(4) . . . . ?
N9 C21 C22 C26 -173(3) . . . . ?
N9 C33 C34 N13 174(3) . . . . ?
N9 C33 C34 C38 -9(4) . . . . ?
N10 C27 C28 N12 2(3) . . . . ?
N10 C27 C28 C32 -178(3) . . . . ?
N10 C33 C34 N13 2(4) . . . . ?
N10 C33 C34 C38 179(2) . . . . ?
N11 C22 C26 C25 -2(4) . . . . ?
N11 C23 C24 C25 1(4) . . . . ?
N12 C28 C32 C31 1(4) . . . . ?
N12 C29 C30 C31 -1(5) . . . . ?
N13 C34 C38 C37 3(4) . . . . ?
N13 C35 C36 C37 5(4) . . . . ?
C21 N8 C27 N10 -2(4) . . . . ?
C21 N8 C27 C28 176(2) . . . . ?
C21 N9 C33 N10 -8(4) . . . . ?
C21 N9 C33 C34 -179(2) . . . . ?
C21 C22 C26 C25 -178(3) . . . . ?
C22 N11 C23 C24 0(4) . . . . ?
C23 N11 C22 C21 177(3) . . . . ?
C23 N11 C22 C26 1(4) . . . . ?
C23 C24 C25 C26 -3(5) . . . . ?
C24 C25 C26 C22 3(4) . . . . ?
C27 N8 C21 N9 -1(4) . . . . ?
C27 N8 C21 C22 -178(3) . . . . ?
C27 N10 C33 N9 6(4) . . . . ?
C27 N10 C33 C34 178(2) . . . . ?
C27 C28 C32 C31 -179(2) . . . . ?
C28 N12 C29 C30 -2(4) . . . . ?
C29 N12 C28 C27 -178(2) . . . . ?
C29 N12 C28 C32 2(4) . . . . ?
C29 C30 C31 C32 3(5) . . . . ?
C30 C31 C32 C28 -3(4) . . . . ?
C33 N9 C21 N8 6(4) . . . . ?
C33 N9 C21 C22 -177(3) . . . . ?
C33 N10 C27 N8 0(4) . . . . ?
C33 N10 C27 C28 -178(2) . . . . ?
C33 C34 C38 C37 -174(3) . . . . ?
C34 N13 C35 C36 -4(5) . . . . ?
C35 N13 C34 C33 177(3) . . . . ?
C35 N13 C34 C38 0(4) . . . . ?
C35 C36 C37 C38 -1(4) . . . . ?
C36 C37 C38 C34 -3(4) . . . . ?
N15 C41 C42 N18 4(4) . . . . ?
N15 C41 C42 C46 -177(3) . . . . ?
N15 C47 C48 N19 3(4) . . . . ?
N15 C47 C48 C52 -176(3) . . . . ?
N16 C41 C42 N18 -179(3) . . . . ?
N16 C41 C42 C46 0(5) . . . . ?
N16 C53 C54 N20 175(3) . . . . ?
N16 C53 C54 C58 3(4) . . . . ?
N17 C47 C48 N19 178(3) . . . . ?
N17 C47 C48 C52 -1(5) . . . . ?
N17 C53 C54 N20 -9(4) . . . . ?
N17 C53 C54 C58 179(3) . . . . ?
N18 C42 C46 C45 2(5) . . . . ?
N18 C43 C44 C45 1(6) . . . . ?
N19 C48 C52 C51 -1(4) . . . . ?
N19 C49 C50 C51 -11(7) . . . . ?
N20 C54 C58 C57 4(4) . . . . ?
N20 C55 C56 C57 -6(6) . . . . ?
C41 N15 C47 N17 5(4) . . . . ?
C41 N15 C47 C48 180(3) . . . . ?
C41 N16 C53 N17 9(5) . . . . ?
C41 N16 C53 C54 -176(3) . . . . ?
C41 C42 C46 C45 -177(3) . . . . ?
C42 N18 C43 C44 0(5) . . . . ?
C43 N18 C42 C41 178(3) . . . . ?
C43 N18 C42 C46 -1(5) . . . . ?
C43 C44 C45 C46 0(6) . . . . ?
C44 C45 C46 C42 -2(5) . . . . ?
C47 N15 C41 N16 2(4) . . . . ?
C47 N15 C41 C42 179(3) . . . . ?
C47 N17 C53 N16 -3(5) . . . . ?
C47 N17 C53 C54 -178(3) . . . . ?
C47 C48 C52 C51 178(3) . . . . ?
C48 N19 C49 C50 6(6) . . . . ?
C49 N19 C48 C47 -179(3) . . . . ?
C49 N19 C48 C52 0(5) . . . . ?
C49 C50 C51 C52 8(6) . . . . ?
C50 C51 C52 C48 -3(4) . . . . ?
C53 N16 C41 N15 -8(5) . . . . ?
C53 N16 C41 C42 175(3) . . . . ?
C53 N17 C47 N15 -4(5) . . . . ?
C53 N17 C47 C48 -179(3) . . . . ?
C53 C54 C58 C57 176(3) . . . . ?
C54 N20 C55 C56 11(6) . . . . ?
C55 N20 C54 C53 178(3) . . . . ?
C55 N20 C54 C58 -9(5) . . . . ?
C55 C56 C57 C58 2(6) . . . . ?
C56 C57 C58 C54 -1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.792(6)
2 0.208(6)

# start Validation Reply Form
_vrf_PLAT434_mo_d8_4601_21sep20_ajp3_0m_b 
;
PROBLEM: Short Inter HL..HL Contact I26      ..I27      .       3.23 Ang.  
RESPONSE: This contact represents an I...I halogen bond
;
_vrf_PLAT342_mo_d8_4601_21sep20_ajp3_0m_b 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04958 Ang.  
RESPONSE: The low C-C bond precision is unsurprisingly given the large portion of
the structure composed of heavy atoms (I and Bi)
;
_vrf_PLAT420_mo_d8_4601_21sep20_ajp3_0m_b 
;
PROBLEM: D-H Bond Without Acceptor  O1       --H2O1     .     Please Check 
RESPONSE: This water molecule serves as both an N-H...O acceptor and O-H...I 
donor
;
####################################################################### 
# 
# 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_mo_d8_5050_14mar21_ajp5_0m
_database_code_depnum_ccdc_archive 'CCDC 2182014'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(I3), 2(C5 H5 N3 S), 2(C15 H13 N9), C2 H3 N'
_chemical_formula_sum            'C42 H39 I12 N25 S2'
_chemical_formula_weight         2480.90
_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'
S S 0.1246 0.1234 '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                   8.0951(4)
_cell_length_b                   12.8879(7)
_cell_length_c                   16.9574(9)
_cell_angle_alpha                78.700(2)
_cell_angle_beta                 89.492(2)
_cell_angle_gamma                77.193(2)
_cell_volume                     1690.59(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.349
_cell_measurement_theta_min      2.582
_shelx_estimated_absorpt_T_max   0.692
_shelx_estimated_absorpt_T_min   0.405
_exptl_absorpt_coefficient_mu    5.609
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0566 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.8735.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.437
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1134
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.071
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            86268
_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         27.875
_diffrn_reflns_theta_min         2.246
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7488
_reflns_number_total             8055
_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 (Bruker, 2018)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         8055
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0139
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0062P)²+1.6614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0277
_refine_ls_wR_factor_ref         0.0286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 HN5-N5 = HN1-N1 = HN7A-N7 = HN7B-N7
 0.86 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
N13 \\sim C21 \\sim C22: within 2A with sigma of 0.003 and sigma for terminal
atoms of 0.006 within 2A
3. Others
 Fixed Sof: N13(0.5) C21(0.5) C22(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C18(H17), C19(H18), C20(H19), C3(H7), C4(H8A), C5(H9), C8(H14), C9(H13),
 C10(H12), C13(H4), C14(H3), C15(H2)
4.b X=CH2 refined with riding coordinates:
 N10(H1,HN10)
4.c Idealised Me refined as rotating group:
 C22(H21A,H21B,H21C)
;
_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
I1 I 0.70650(2) 0.23417(2) 0.07670(2) 0.02400(3) Uani 1 1 d . . . . .
I2 I 0.76149(2) 0.10585(2) 0.23460(2) 0.01663(3) Uani 1 1 d . . . . .
I3 I 0.81278(2) -0.03532(2) 0.40009(2) 0.02486(3) Uani 1 1 d . . . . .
I4 I -0.11376(2) 0.38778(2) 0.25125(2) 0.02117(3) Uani 1 1 d . . . . .
I5 I -0.01401(2) 0.59472(2) 0.22916(2) 0.01731(3) Uani 1 1 d . . . . .
I6 I 0.07572(2) 0.80580(2) 0.20576(2) 0.02746(3) Uani 1 1 d . . . . .
S1 S 0.17205(6) 0.41909(4) 0.42176(3) 0.02094(10) Uani 1 1 d . . . . .
N10 N 0.2368(2) 0.39416(16) 0.57798(10) 0.0268(4) Uani 1 1 d . . . . .
H1 H 0.308135 0.375564 0.619853 0.032 Uiso 1 1 calc R U . . .
HN10 H 0.128335 0.419892 0.584129 0.032 Uiso 1 1 calc R U . . .
N11 N 0.5344(2) 0.29119(13) 0.44046(9) 0.0173(3) Uani 1 1 d . . . . .
N12 N 0.5780(2) 0.35234(14) 0.56095(10) 0.0193(3) Uani 1 1 d . . . . .
C16 C 0.2924(2) 0.38346(16) 0.50602(11) 0.0181(4) Uani 1 1 d . . . . .
C17 C 0.4803(2) 0.33859(15) 0.50258(11) 0.0162(4) Uani 1 1 d . . . . .
C18 C 0.7464(2) 0.31712(17) 0.55551(12) 0.0222(4) Uani 1 1 d . . . . .
H17 H 0.820176 0.324708 0.596244 0.027 Uiso 1 1 calc R U . . .
C19 C 0.8150(3) 0.27051(17) 0.49281(12) 0.0219(4) Uani 1 1 d . . . . .
H18 H 0.934178 0.248093 0.488459 0.026 Uiso 1 1 calc R U . . .
C20 C 0.7026(2) 0.25772(16) 0.43629(12) 0.0199(4) Uani 1 1 d . . . . .
H19 H 0.746202 0.224051 0.393066 0.024 Uiso 1 1 calc R U . . .
N1 N 0.4430(2) 0.54109(13) 0.16111(9) 0.0151(3) Uani 1 1 d D . . . .
HN1 H 0.449(3) 0.5809(17) 0.1172(11) 0.019(6) Uiso 1 1 d D . . . .
N2 N 0.26876(19) 0.32216(13) 0.13031(9) 0.0149(3) Uani 1 1 d . . . . .
N3 N 0.2778(2) 0.47501(13) 0.02343(9) 0.0181(3) Uani 1 1 d . . . . .
N4 N 0.39288(19) 0.37008(13) 0.23097(9) 0.0145(3) Uani 1 1 d . . . . .
N5 N 0.3521(2) 0.19110(13) 0.34320(9) 0.0162(3) Uani 1 1 d D . . . .
HN5 H 0.390(3) 0.2418(17) 0.3575(15) 0.033(7) Uiso 1 1 d D . . . .
N6 N 0.2416(2) 0.12236(13) 0.24142(10) 0.0181(3) Uani 1 1 d . . . . .
N7 N 0.4529(2) 0.54249(14) 0.29783(10) 0.0172(3) Uani 1 1 d D . . . .
HN7A H 0.422(3) 0.4830(15) 0.3097(14) 0.026(6) Uiso 1 1 d D . . . .
HN7B H 0.461(3) 0.578(2) 0.3346(13) 0.034(7) Uiso 1 1 d D . . . .
N8 N 0.5578(2) 0.73583(14) 0.26071(10) 0.0180(3) Uani 1 1 d . . . . .
N9 N 0.5133(2) 0.73213(14) 0.12202(10) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.3865(2) 0.44617(15) 0.16467(11) 0.0145(3) Uani 1 1 d . . . . .
C2 C 0.3104(2) 0.42078(15) 0.09953(11) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.1975(3) 0.42984(17) -0.02296(12) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.172467 0.465357 -0.077510 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1466(3) 0.33093(18) 0.00447(12) 0.0230(4) Uani 1 1 d . . . . .
H8A H 0.086947 0.302584 -0.031218 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1827(2) 0.27656(17) 0.08155(12) 0.0205(4) Uani 1 1 d . . . . .
H9 H 0.150001 0.210009 0.101006 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3221(2) 0.29414(15) 0.21016(11) 0.0154(4) Uani 1 1 d . . . . .
C7 C 0.3036(2) 0.19926(15) 0.26545(11) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.3398(3) 0.10449(17) 0.39914(12) 0.0217(4) Uani 1 1 d . . . . .
H14 H 0.376346 0.098669 0.453228 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2739(3) 0.02416(17) 0.37789(13) 0.0251(4) Uani 1 1 d . . . . .
H13 H 0.261335 -0.037502 0.416562 0.030 Uiso 1 1 calc R U . . .
C10 C 0.2265(3) 0.03664(17) 0.29755(12) 0.0220(4) Uani 1 1 d . . . . .
H12 H 0.181071 -0.018370 0.281667 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4690(2) 0.58554(15) 0.22285(11) 0.0148(3) Uani 1 1 d . . . . .
C12 C 0.5172(2) 0.69235(15) 0.20067(11) 0.0155(4) Uani 1 1 d . . . . .
C13 C 0.5915(3) 0.83449(18) 0.23798(13) 0.0245(4) Uani 1 1 d . . . . .
H4 H 0.621827 0.869816 0.278031 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5835(3) 0.88640(19) 0.15821(14) 0.0301(5) Uani 1 1 d . . . . .
H3 H 0.602844 0.957586 0.143114 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5463(3) 0.83063(18) 0.10105(13) 0.0260(4) Uani 1 1 d . . . . .
H2 H 0.544112 0.863302 0.045637 0.031 Uiso 1 1 calc R U . . .
N13 N 0.2108(6) 0.0422(3) 0.0254(3) 0.0379(9) Uani 0.5 1 d . U P A -1
C21 C 0.087(3) 0.013(2) 0.0078(18) 0.037(2) Uani 0.5 1 d . U P A -1
C22 C -0.064(3) -0.021(2) -0.0115(17) 0.037(3) Uani 0.5 1 d . U P A -1
H21A H -0.052174 -0.044083 -0.063446 0.056 Uiso 0.5 1 calc R U P A -1
H21B H -0.163254 0.039421 -0.014569 0.056 Uiso 0.5 1 calc R U P A -1
H21C H -0.079720 -0.082009 0.030454 0.056 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.8393(2) . ?
I2 I3 3.0071(2) . ?
I4 I5 2.9091(2) . ?
I5 I6 2.9213(2) . ?
S1 C16 1.6646(19) . ?
N10 H1 0.8800 . ?
N10 HN10 0.8800 . ?
N10 C16 1.319(2) . ?
N11 C17 1.342(2) . ?
N11 C20 1.340(2) . ?
N12 C17 1.335(2) . ?
N12 C18 1.347(3) . ?
C16 C17 1.508(3) . ?
C18 H17 0.9500 . ?
C18 C19 1.375(3) . ?
C19 H18 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H19 0.9500 . ?
N1 HN1 0.826(16) . ?
N1 C1 1.389(2) . ?
N1 C11 1.327(2) . ?
N2 C2 1.389(2) . ?
N2 C5 1.377(2) . ?
N2 C6 1.378(2) . ?
N3 C2 1.339(2) . ?
N3 C3 1.318(2) . ?
N4 C1 1.332(2) . ?
N4 C6 1.341(2) . ?
N5 HN5 0.857(16) . ?
N5 C7 1.357(2) . ?
N5 C8 1.337(3) . ?
N6 C7 1.335(2) . ?
N6 C10 1.337(3) . ?
N7 HN7A 0.847(16) . ?
N7 HN7B 0.856(16) . ?
N7 C11 1.302(2) . ?
N8 C12 1.330(2) . ?
N8 C13 1.341(3) . ?
N9 C12 1.330(2) . ?
N9 C15 1.334(3) . ?
C1 C2 1.396(2) . ?
C3 H7 0.9500 . ?
C3 C4 1.417(3) . ?
C4 H8A 0.9500 . ?
C4 C5 1.357(3) . ?
C5 H9 0.9500 . ?
C6 C7 1.423(3) . ?
C8 H14 0.9500 . ?
C8 C9 1.371(3) . ?
C9 H13 0.9500 . ?
C9 C10 1.388(3) . ?
C10 H12 0.9500 . ?
C11 C12 1.491(3) . ?
C13 H4 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H3 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H2 0.9500 . ?
N13 C21 1.20(3) . ?
C21 C22 1.457(6) . ?
C22 H21A 0.9800 . ?
C22 H21B 0.9800 . ?
C22 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 I2 I3 177.985(6) . . ?
I4 I5 I6 178.304(6) . . ?
H1 N10 HN10 120.0 . . ?
C16 N10 H1 120.0 . . ?
C16 N10 HN10 120.0 . . ?
C20 N11 C17 116.13(16) . . ?
C17 N12 C18 116.44(17) . . ?
N10 C16 S1 124.75(15) . . ?
N10 C16 C17 115.45(16) . . ?
C17 C16 S1 119.77(14) . . ?
N11 C17 C16 117.36(16) . . ?
N12 C17 N11 126.06(17) . . ?
N12 C17 C16 116.56(16) . . ?
N12 C18 H17 119.0 . . ?
N12 C18 C19 122.04(18) . . ?
C19 C18 H17 119.0 . . ?
C18 C19 H18 121.5 . . ?
C18 C19 C20 116.98(18) . . ?
C20 C19 H18 121.5 . . ?
N11 C20 C19 122.29(18) . . ?
N11 C20 H19 118.9 . . ?
C19 C20 H19 118.9 . . ?
C1 N1 HN1 120.1(16) . . ?
C11 N1 HN1 112.7(16) . . ?
C11 N1 C1 126.55(16) . . ?
C5 N2 C2 119.29(16) . . ?
C5 N2 C6 133.95(17) . . ?
C6 N2 C2 106.68(15) . . ?
C3 N3 C2 115.58(17) . . ?
C1 N4 C6 106.01(15) . . ?
C7 N5 HN5 120.5(18) . . ?
C8 N5 HN5 118.7(18) . . ?
C8 N5 C7 120.77(17) . . ?
C7 N6 C10 117.28(17) . . ?
HN7A N7 HN7B 120(2) . . ?
C11 N7 HN7A 120.0(17) . . ?
C11 N7 HN7B 119.8(18) . . ?
C12 N8 C13 114.81(17) . . ?
C12 N9 C15 115.63(17) . . ?
N1 C1 C2 123.87(17) . . ?
N4 C1 N1 124.34(16) . . ?
N4 C1 C2 111.76(16) . . ?
N2 C2 C1 104.54(15) . . ?
N3 C2 N2 124.56(16) . . ?
N3 C2 C1 130.89(18) . . ?
N3 C3 H7 118.4 . . ?
N3 C3 C4 123.28(18) . . ?
C4 C3 H7 118.4 . . ?
C3 C4 H8A 119.9 . . ?
C5 C4 C3 120.22(18) . . ?
C5 C4 H8A 119.9 . . ?
N2 C5 H9 121.5 . . ?
C4 C5 N2 117.04(18) . . ?
C4 C5 H9 121.5 . . ?
N2 C6 C7 125.97(17) . . ?
N4 C6 N2 111.00(16) . . ?
N4 C6 C7 123.02(16) . . ?
N5 C7 C6 116.75(16) . . ?
N6 C7 N5 121.99(17) . . ?
N6 C7 C6 121.26(17) . . ?
N5 C8 H14 120.2 . . ?
N5 C8 C9 119.54(19) . . ?
C9 C8 H14 120.2 . . ?
C8 C9 H13 121.4 . . ?
C8 C9 C10 117.24(19) . . ?
C10 C9 H13 121.4 . . ?
N6 C10 C9 123.15(19) . . ?
N6 C10 H12 118.4 . . ?
C9 C10 H12 118.4 . . ?
N1 C11 C12 114.94(16) . . ?
N7 C11 N1 124.31(18) . . ?
N7 C11 C12 120.74(17) . . ?
N8 C12 C11 117.04(16) . . ?
N9 C12 N8 128.29(18) . . ?
N9 C12 C11 114.67(16) . . ?
N8 C13 H4 118.9 . . ?
N8 C13 C14 122.14(19) . . ?
C14 C13 H4 118.9 . . ?
C13 C14 H3 121.3 . . ?
C13 C14 C15 117.4(2) . . ?
C15 C14 H3 121.3 . . ?
N9 C15 C14 121.6(2) . . ?
N9 C15 H2 119.2 . . ?
C14 C15 H2 119.2 . . ?
N13 C21 C22 178.5(15) . . ?
C21 C22 H21A 109.5 . . ?
C21 C22 H21B 109.5 . . ?
C21 C22 H21C 109.5 . . ?
H21A C22 H21B 109.5 . . ?
H21A C22 H21C 109.5 . . ?
H21B C22 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C16 C17 N11 -24.6(2) . . . . ?
S1 C16 C17 N12 153.75(15) . . . . ?
N10 C16 C17 N11 157.24(19) . . . . ?
N10 C16 C17 N12 -24.4(3) . . . . ?
N12 C18 C19 C20 -2.1(3) . . . . ?
C17 N11 C20 C19 0.3(3) . . . . ?
C17 N12 C18 C19 0.7(3) . . . . ?
C18 N12 C17 N11 1.5(3) . . . . ?
C18 N12 C17 C16 -176.75(17) . . . . ?
C18 C19 C20 N11 1.6(3) . . . . ?
C20 N11 C17 N12 -2.0(3) . . . . ?
C20 N11 C17 C16 176.24(17) . . . . ?
N1 C1 C2 N2 -177.78(16) . . . . ?
N1 C1 C2 N3 1.3(3) . . . . ?
N1 C11 C12 N8 -174.76(16) . . . . ?
N1 C11 C12 N9 5.4(2) . . . . ?
N2 C6 C7 N5 -174.71(17) . . . . ?
N2 C6 C7 N6 5.4(3) . . . . ?
N3 C3 C4 C5 -1.2(3) . . . . ?
N4 C1 C2 N2 0.1(2) . . . . ?
N4 C1 C2 N3 179.20(18) . . . . ?
N4 C6 C7 N5 3.9(3) . . . . ?
N4 C6 C7 N6 -175.97(17) . . . . ?
N5 C8 C9 C10 1.4(3) . . . . ?
N7 C11 C12 N8 6.0(3) . . . . ?
N7 C11 C12 N9 -173.76(17) . . . . ?
N8 C13 C14 C15 -2.8(3) . . . . ?
C1 N1 C11 N7 3.7(3) . . . . ?
C1 N1 C11 C12 -175.48(16) . . . . ?
C1 N4 C6 N2 -0.5(2) . . . . ?
C1 N4 C6 C7 -179.31(17) . . . . ?
C2 N2 C5 C4 1.4(3) . . . . ?
C2 N2 C6 N4 0.6(2) . . . . ?
C2 N2 C6 C7 179.37(17) . . . . ?
C2 N3 C3 C4 0.4(3) . . . . ?
C3 N3 C2 N2 1.4(3) . . . . ?
C3 N3 C2 C1 -177.48(19) . . . . ?
C3 C4 C5 N2 0.2(3) . . . . ?
C5 N2 C2 N3 -2.4(3) . . . . ?
C5 N2 C2 C1 176.74(16) . . . . ?
C5 N2 C6 N4 -175.98(19) . . . . ?
C5 N2 C6 C7 2.8(3) . . . . ?
C6 N2 C2 N3 -179.56(17) . . . . ?
C6 N2 C2 C1 -0.44(19) . . . . ?
C6 N2 C5 C4 177.66(19) . . . . ?
C6 N4 C1 N1 178.13(17) . . . . ?
C6 N4 C1 C2 0.2(2) . . . . ?
C7 N5 C8 C9 -1.4(3) . . . . ?
C7 N6 C10 C9 -0.9(3) . . . . ?
C8 N5 C7 N6 0.2(3) . . . . ?
C8 N5 C7 C6 -179.73(17) . . . . ?
C8 C9 C10 N6 -0.3(3) . . . . ?
C10 N6 C7 N5 1.0(3) . . . . ?
C10 N6 C7 C6 -179.14(17) . . . . ?
C11 N1 C1 N4 -19.0(3) . . . . ?
C11 N1 C1 C2 158.64(18) . . . . ?
C12 N8 C13 C14 0.3(3) . . . . ?
C12 N9 C15 C14 0.6(3) . . . . ?
C13 N8 C12 N9 3.2(3) . . . . ?
C13 N8 C12 C11 -176.61(16) . . . . ?
C13 C14 C15 N9 2.3(3) . . . . ?
C15 N9 C12 N8 -3.6(3) . . . . ?
C15 N9 C12 C11 176.17(17) . . . . ?

_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_nicotin_a
_database_code_depnum_ccdc_archive 'CCDC 2182004'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(I5), 2(C2 H3 N), C18 H15 N6'
_chemical_formula_sum            'C22 H21 I15 N8'
_chemical_formula_weight         2300.97
_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'

_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                   7.3464(2)
_cell_length_b                   26.9370(4)
_cell_length_c                   24.3715(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.853(2)
_cell_angle_gamma                90
_cell_volume                     4805.58(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    117800
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.371
_cell_measurement_theta_min      1.512
_shelx_estimated_absorpt_T_max   0.546
_shelx_estimated_absorpt_T_min   0.224
_exptl_absorpt_coefficient_mu    9.686
_exptl_absorpt_correction_T_max  0.732
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.180
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4016
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.071
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            117800
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.512
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8421
_reflns_number_total             9825
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         3.074
_refine_diff_density_min         -2.431
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         9825
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0107P)²+17.2779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0477
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 HN6-N6 = HN4-N4 = HN5-N5
 0.85 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5A), C6(H6A), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.13475(5) 0.95792(2) 0.43209(2) 0.03392(9) Uani 1 1 d . . . . .
I2 I 0.31819(5) 0.94896(2) 0.53533(2) 0.02845(9) Uani 1 1 d . . . . .
I3 I 0.50730(5) 0.94663(2) 0.66035(2) 0.02736(8) Uani 1 1 d . . . . .
I4 I 0.47906(4) 0.83421(2) 0.68503(2) 0.02464(8) Uani 1 1 d . . . . .
I5 I 0.44726(5) 0.73109(2) 0.69936(2) 0.02931(9) Uani 1 1 d . . . . .
N8 N 0.7812(7) 0.85651(17) 0.5516(2) 0.0375(12) Uani 1 1 d . . . . .
C21 C 0.8718(8) 0.8759(2) 0.5858(3) 0.0331(14) Uani 1 1 d . . . . .
C22 C 0.9801(7) 0.8965(2) 0.6326(2) 0.0349(14) Uani 1 1 d . . . . .
H22A H 0.923093 0.889086 0.665708 0.052 Uiso 1 1 calc R U . . .
H22B H 0.988802 0.931832 0.628450 0.052 Uiso 1 1 calc R U . . .
H22C H 1.100238 0.882240 0.634879 0.052 Uiso 1 1 calc R U . . .
I6 I -0.12719(5) 0.51319(2) 0.78739(2) 0.02905(9) Uani 1 1 d . . . . .
I7 I 0.16652(5) 0.54909(2) 0.73616(2) 0.02520(8) Uani 1 1 d . . . . .
I8 I 0.51325(5) 0.59317(2) 0.67372(2) 0.02715(8) Uani 1 1 d . . . . .
I9 I 0.31308(4) 0.61289(2) 0.56180(2) 0.02406(8) Uani 1 1 d . . . . .
I10 I 0.12607(5) 0.63510(2) 0.45841(2) 0.03093(9) Uani 1 1 d . . . . .
I11 I 0.25921(5) 0.77001(2) 0.55218(2) 0.03353(9) Uani 1 1 d . . . . .
I12 I 0.13104(4) 0.79739(2) 0.44613(2) 0.02209(8) Uani 1 1 d . . . . .
I13 I 0.00432(5) 0.82214(2) 0.32321(2) 0.02556(8) Uani 1 1 d . . . . .
I14 I -0.04157(4) 0.71005(2) 0.30787(2) 0.02334(8) Uani 1 1 d . . . . .
I15 I -0.08421(4) 0.60585(2) 0.29595(2) 0.02530(8) Uani 1 1 d . . . . .
N1 N 0.6547(5) 0.67006(14) 0.47460(16) 0.0177(9) Uani 1 1 d . . . . .
N2 N 0.6752(5) 0.75796(14) 0.48317(16) 0.0177(9) Uani 1 1 d . . . . .
N3 N 0.5579(5) 0.72223(14) 0.39838(16) 0.0157(9) Uani 1 1 d . . . . .
N4 N 0.7972(5) 0.74962(16) 0.58877(18) 0.0222(9) Uani 1 1 d D . . . .
HN4 H 0.765(7) 0.7756(13) 0.570(2) 0.036(17) Uiso 1 1 d D . . . .
N5 N 0.6367(6) 0.84935(15) 0.43984(19) 0.0228(10) Uani 1 1 d D . . . .
HN5 H 0.681(8) 0.845(2) 0.4729(12) 0.06(2) Uiso 1 1 d D . . . .
N6 N 0.5811(6) 0.58931(15) 0.41195(18) 0.0214(9) Uani 1 1 d D . . . .
HN6 H 0.630(7) 0.589(2) 0.4447(11) 0.034(17) Uiso 1 1 d D . . . .
C1 C 0.6967(6) 0.71183(17) 0.50288(19) 0.0166(10) Uani 1 1 d . . . . .
C2 C 0.6073(6) 0.76064(17) 0.4308(2) 0.0179(11) Uani 1 1 d . . . . .
C3 C 0.5854(6) 0.67800(17) 0.4231(2) 0.0167(10) Uani 1 1 d . . . . .
C4 C 0.7748(6) 0.70702(18) 0.5598(2) 0.0189(11) Uani 1 1 d . . . . .
C5 C 0.8754(7) 0.7512(2) 0.6400(2) 0.0265(12) Uani 1 1 d . . . . .
H5A H 0.887949 0.781437 0.658462 0.032 Uiso 1 1 calc R U . . .
C6 C 0.9380(7) 0.7082(2) 0.6659(2) 0.0284(13) Uani 1 1 d . . . . .
H6A H 0.993932 0.709110 0.701588 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9161(7) 0.6636(2) 0.6378(2) 0.0259(12) Uani 1 1 d . . . . .
H7 H 0.956702 0.634175 0.654579 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8329(6) 0.66323(19) 0.5845(2) 0.0219(11) Uani 1 1 d . . . . .
H8 H 0.816707 0.633412 0.565433 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5845(6) 0.81081(17) 0.4064(2) 0.0173(10) Uani 1 1 d . . . . .
C10 C 0.6233(7) 0.89649(19) 0.4231(2) 0.0282(13) Uani 1 1 d . . . . .
H10 H 0.661503 0.922167 0.446900 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5518(7) 0.9066(2) 0.3699(2) 0.0318(14) Uani 1 1 d . . . . .
H11 H 0.539690 0.939277 0.357803 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4989(7) 0.8684(2) 0.3351(2) 0.0284(13) Uani 1 1 d . . . . .
H12 H 0.451347 0.874954 0.299212 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5166(6) 0.81950(18) 0.3536(2) 0.0213(11) Uani 1 1 d . . . . .
H13 H 0.482607 0.793214 0.330186 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5353(6) 0.63384(17) 0.38948(19) 0.0175(10) Uani 1 1 d . . . . .
C15 C 0.5423(7) 0.54620(18) 0.3857(2) 0.0246(12) Uani 1 1 d . . . . .
H15 H 0.575449 0.516106 0.402396 0.029 Uiso 1 1 calc R U . . .
C16 C 0.4528(7) 0.54735(19) 0.3339(2) 0.0252(12) Uani 1 1 d . . . . .
H16 H 0.425252 0.517850 0.315141 0.030 Uiso 1 1 calc R U . . .
C17 C 0.4036(6) 0.59229(18) 0.3095(2) 0.0217(11) Uani 1 1 d . . . . .
H17 H 0.342374 0.593214 0.274505 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4462(6) 0.63570(18) 0.3377(2) 0.0180(11) Uani 1 1 d . . . . .
H18 H 0.414749 0.666169 0.321597 0.022 Uiso 1 1 calc R U . . .
N7 N 0.7535(7) 0.54046(18) 0.5074(2) 0.0380(12) Uani 1 1 d . . . . .
C19 C 0.8310(7) 0.52495(19) 0.5452(2) 0.0271(12) Uani 1 1 d . . . . .
C20 C 0.9323(8) 0.5059(2) 0.5947(2) 0.0344(14) Uani 1 1 d . . . . .
H20A H 0.873448 0.516275 0.626455 0.052 Uiso 1 1 calc R U . . .
H20B H 1.054746 0.518683 0.596942 0.052 Uiso 1 1 calc R U . . .
H20C H 0.935485 0.470349 0.593199 0.052 Uiso 1 1 calc R U . . .


_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
I1 I2 2.7626(5) . ?
I2 I3 3.2406(5) . ?
I3 I4 3.0976(5) . ?
I4 I5 2.8118(5) . ?
N8 C21 1.147(7) . ?
C21 C22 1.446(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
I6 I7 2.7578(5) . ?
I7 I8 3.2969(5) . ?
I8 I9 3.0341(5) . ?
I9 I10 2.8301(5) . ?
I11 I12 2.7747(5) . ?
I12 I13 3.1327(5) . ?
I13 I14 3.0576(5) . ?
I14 I15 2.8364(5) . ?
N1 C1 1.342(6) . ?
N1 C3 1.332(6) . ?
N2 C1 1.337(6) . ?
N2 C2 1.333(6) . ?
N3 C2 1.333(6) . ?
N3 C3 1.342(6) . ?
N4 HN4 0.855(19) . ?
N4 C4 1.350(6) . ?
N4 C5 1.331(6) . ?
N5 HN5 0.85(2) . ?
N5 C9 1.355(6) . ?
N5 C10 1.334(6) . ?
N6 HN6 0.848(19) . ?
N6 C14 1.349(6) . ?
N6 C15 1.344(6) . ?
C1 C4 1.462(7) . ?
C2 C9 1.480(6) . ?
C3 C14 1.473(6) . ?
C4 C8 1.375(6) . ?
C5 H5A 0.9300 . ?
C5 C6 1.380(7) . ?
C6 H6A 0.9300 . ?
C6 C7 1.384(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(7) . ?
C8 H8 0.9300 . ?
C9 C13 1.361(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(7) . ?
C13 H13 0.9300 . ?
C14 C18 1.374(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(7) . ?
C18 H18 0.9300 . ?
N7 C19 1.122(6) . ?
C19 C20 1.455(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 I2 I3 174.480(16) . . ?
I4 I3 I2 99.851(13) . . ?
I5 I4 I3 175.922(16) . . ?
N8 C21 C22 174.1(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
I6 I7 I8 179.095(16) . . ?
I9 I8 I7 98.243(13) . . ?
I10 I9 I8 177.859(16) . . ?
I11 I12 I13 175.794(16) . . ?
I14 I13 I12 85.847(12) . . ?
I15 I14 I13 178.850(16) . . ?
C3 N1 C1 113.8(4) . . ?
C2 N2 C1 114.7(4) . . ?
C2 N3 C3 113.6(4) . . ?
C4 N4 HN4 114(4) . . ?
C5 N4 HN4 123(4) . . ?
C5 N4 C4 122.8(5) . . ?
C9 N5 HN5 123(4) . . ?
C10 N5 HN5 115(4) . . ?
C10 N5 C9 122.4(5) . . ?
C14 N6 HN6 117(4) . . ?
C15 N6 HN6 120(4) . . ?
C15 N6 C14 122.6(5) . . ?
N1 C1 C4 117.9(4) . . ?
N2 C1 N1 125.4(4) . . ?
N2 C1 C4 116.7(4) . . ?
N2 C2 N3 125.9(4) . . ?
N2 C2 C9 117.0(4) . . ?
N3 C2 C9 117.1(4) . . ?
N1 C3 N3 126.6(4) . . ?
N1 C3 C14 116.9(4) . . ?
N3 C3 C14 116.5(4) . . ?
N4 C4 C1 116.2(4) . . ?
N4 C4 C8 118.8(5) . . ?
C8 C4 C1 125.0(5) . . ?
N4 C5 H5A 119.9 . . ?
N4 C5 C6 120.1(5) . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 H6A 120.6 . . ?
C5 C6 C7 118.8(5) . . ?
C7 C6 H6A 120.6 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(5) . . ?
C8 C7 H7 120.2 . . ?
C4 C8 C7 119.8(5) . . ?
C4 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
N5 C9 C2 116.2(4) . . ?
N5 C9 C13 120.0(4) . . ?
C13 C9 C2 123.8(4) . . ?
N5 C10 H10 120.5 . . ?
N5 C10 C11 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(5) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C9 C13 C12 119.1(5) . . ?
C9 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N6 C14 C3 116.8(4) . . ?
N6 C14 C18 119.2(4) . . ?
C18 C14 C3 124.0(4) . . ?
N6 C15 H15 120.5 . . ?
N6 C15 C16 118.9(5) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(5) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(5) . . ?
C18 C17 H17 120.4 . . ?
C14 C18 C17 119.8(5) . . ?
C14 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N7 C19 C20 178.7(6) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C22 H22A I15 0.96 3.18 4.048(6) 150.9 4_676 yes
C22 H22B I6 0.96 3.11 3.807(5) 130.5 2_656 yes
C22 H22C I4 0.96 3.22 4.134(6) 160.9 1_655 yes
N4 HN4 N8 0.855(19) 2.23(3) 3.018(6) 153(5) . yes
N4 HN4 N2 0.855(19) 2.22(5) 2.662(6) 112(4) . yes
N5 HN5 N8 0.85(2) 2.02(3) 2.845(7) 164(6) . yes
N6 HN6 N7 0.848(19) 2.15(4) 2.872(6) 142(5) . yes
C6 H6A I13 0.93 3.08 3.910(5) 150.1 4_676 yes
C11 H11 I3 0.93 3.12 4.038(5) 169.6 3_676 yes
C13 H13 I5 0.93 3.24 3.990(5) 138.7 4_575 yes
C16 H16 I6 0.93 3.29 3.990(5) 133.9 3_566 yes
C16 H16 I8 0.93 3.03 3.799(5) 140.7 3_666 yes
C20 H20C I10 0.96 3.12 4.025(6) 156.9 3_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C4 N4 -173.2(4) . . . . ?
N1 C1 C4 C8 9.8(7) . . . . ?
N1 C3 C14 N6 -6.5(6) . . . . ?
N1 C3 C14 C18 173.4(4) . . . . ?
N2 C1 C4 N4 7.5(6) . . . . ?
N2 C1 C4 C8 -169.5(4) . . . . ?
N2 C2 C9 N5 0.6(6) . . . . ?
N2 C2 C9 C13 -179.8(4) . . . . ?
N3 C2 C9 N5 -179.5(4) . . . . ?
N3 C2 C9 C13 0.1(7) . . . . ?
N3 C3 C14 N6 172.9(4) . . . . ?
N3 C3 C14 C18 -7.2(7) . . . . ?
N4 C4 C8 C7 -1.2(7) . . . . ?
N4 C5 C6 C7 -0.7(8) . . . . ?
N5 C9 C13 C12 -1.2(7) . . . . ?
N5 C10 C11 C12 -1.1(8) . . . . ?
N6 C14 C18 C17 0.5(7) . . . . ?
N6 C15 C16 C17 -0.2(7) . . . . ?
C1 N1 C3 N3 0.8(6) . . . . ?
C1 N1 C3 C14 -179.8(4) . . . . ?
C1 N2 C2 N3 1.5(6) . . . . ?
C1 N2 C2 C9 -178.7(4) . . . . ?
C1 C4 C8 C7 175.8(4) . . . . ?
C2 N2 C1 N1 -0.6(6) . . . . ?
C2 N2 C1 C4 178.6(4) . . . . ?
C2 N3 C3 N1 -0.1(6) . . . . ?
C2 N3 C3 C14 -179.5(4) . . . . ?
C2 C9 C13 C12 179.2(4) . . . . ?
C3 N1 C1 N2 -0.4(6) . . . . ?
C3 N1 C1 C4 -179.6(4) . . . . ?
C3 N3 C2 N2 -1.2(6) . . . . ?
C3 N3 C2 C9 179.0(4) . . . . ?
C3 C14 C18 C17 -179.4(4) . . . . ?
C4 N4 C5 C6 0.1(7) . . . . ?
C5 N4 C4 C1 -176.3(4) . . . . ?
C5 N4 C4 C8 0.9(7) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
C6 C7 C8 C4 0.6(7) . . . . ?
C9 N5 C10 C11 0.7(7) . . . . ?
C10 N5 C9 C2 -179.9(4) . . . . ?
C10 N5 C9 C13 0.5(7) . . . . ?
C10 C11 C12 C13 0.3(8) . . . . ?
C11 C12 C13 C9 0.8(7) . . . . ?
C14 N6 C15 C16 0.1(7) . . . . ?
C15 N6 C14 C3 179.6(4) . . . . ?
C15 N6 C14 C18 -0.3(7) . . . . ?
C15 C16 C17 C18 0.4(7) . . . . ?
C16 C17 C18 C14 -0.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT434_nicotin_a           
;
PROBLEM: Short Inter HL..HL Contact I2       ..I3       .       3.24 Ang.  
RESPONSE: This contact represents an I...I halogen bond
;
####################################################################### 
# 
# 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_mo_d8_4596_20sep20_ajp4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2182005'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '10.144(I2), 2.856(C2 H3 N), C36 H26 Fe N12'
_chemical_formula_sum            'C41.71 H34.57 Fe I20.29 N14.86'
_chemical_formula_weight         3374.55
_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'
Fe Fe 0.3463 0.8444 '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                   13.3176(6)
_cell_length_b                   16.6001(7)
_cell_length_c                   19.8556(8)
_cell_angle_alpha                103.605(2)
_cell_angle_beta                 96.773(2)
_cell_angle_gamma                111.876(2)
_cell_volume                     3854.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9599
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.513
_shelx_estimated_absorpt_T_min   0.193
_exptl_absorpt_coefficient_mu    8.359
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.907
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2980
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            145950
_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         26.372
_diffrn_reflns_theta_min         1.985
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                14074
_reflns_number_total             15754
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         4.522
_refine_diff_density_min         -3.633
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     759
_refine_ls_number_reflns         15754
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.089
_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)+(0.0167P)²+50.5551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 HN6-N6
 0.86 with sigma of 0.02
 HN12-N12
 0.86 with sigma of 0.02
 C43-C44
 1.45 with sigma of 0.02
 N16-C44
 0.001 with sigma of 2.6
2. Uiso/Uaniso restraints and constraints
C43 \\sim C44: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
N15 \\sim C41 \\sim C42: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
Uanis(C41) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C42) \\sim Ueq, Uanis(C44) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N16) = Uanis(C43)
3. Others
 1*[Sof(I22A)+Sof(I23A)]+1*[Sof(N15)+Sof(C41)+Sof(C42)+Sof(H42A)+Sof(H42B)+
 Sof(H42C)]+1*[Sof(N16)+Sof(C43)+Sof(C44)+Sof(H44A)+Sof(H44B)+Sof(H44C)]=1 with
 esd of 0.0001
 Sof(I22A)=Sof(I23A)=FVAR(1)
 Sof(N15)=Sof(C41)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=FVAR(2)
 Sof(N16)=Sof(C43)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(3)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6A), C9(H9), C10(H10), C11(H11), C12(H12A),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24),
  C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36)
4.b Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C44(H44A,H44B,H44C), C38(H38A,H38B,H38C), C40(H40A,H40B,
 H40C)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.44284(4) 0.69841(3) -0.06129(3) 0.03347(10) Uani 1 1 d . . . . .
I2 I 0.32544(4) 0.79869(3) -0.01564(3) 0.03105(10) Uani 1 1 d . . . . .
I3 I 0.18810(4) 0.91115(3) 0.04184(3) 0.03326(10) Uani 1 1 d . . . . .
I4 I 0.42026(4) 1.05770(3) 0.13169(3) 0.03570(11) Uani 1 1 d . . . . .
I5 I 0.63097(5) 1.17656(4) 0.21591(3) 0.04981(15) Uani 1 1 d . . . . .
I6 I 0.500000 0.500000 0.000000 0.03612(16) Uani 1 2 d S . P . .
I7 I 0.59482(5) 0.55949(4) -0.11379(4) 0.05079(15) Uani 1 1 d . . . . .
I8 I 0.05026(5) 0.03995(4) 0.10937(3) 0.03736(11) Uani 1 1 d . . . . .
I9 I -0.03361(4) 0.14437(3) 0.19441(2) 0.03375(10) Uani 1 1 d . . . . .
I10 I 0.23431(4) 0.51195(4) 0.24136(3) 0.03870(11) Uani 1 1 d . . . . .
I11 I 0.11368(4) 0.58213(3) 0.32257(3) 0.03321(10) Uani 1 1 d . . . . .
I12 I -0.09271(4) 0.29122(3) 0.29991(3) 0.03399(11) Uani 1 1 d . . . . .
I13 I 0.12966(4) 0.36942(3) 0.39764(2) 0.02505(9) Uani 1 1 d . . . . .
I14 I 0.34505(4) 0.45291(3) 0.49188(3) 0.03333(10) Uani 1 1 d . . . . .
I15 I -0.03514(5) 0.66128(4) 0.40819(3) 0.04616(14) Uani 1 1 d . . . . .
I16 I -0.01848(3) 0.76520(3) 0.29538(2) 0.02619(9) Uani 1 1 d . . . . .
I17 I -0.00350(4) 0.85607(4) 0.19319(3) 0.03438(11) Uani 1 1 d . . . . .
I18 I 0.15610(4) 0.18598(3) 0.53309(2) 0.02849(9) Uani 1 1 d . . . . .
I19 I 0.21035(4) 0.04207(3) 0.48252(2) 0.02810(9) Uani 1 1 d . . . . .
I20 I 0.500000 0.000000 0.500000 0.02557(12) Uani 1 2 d S . P . .
I21 I 0.27419(4) -0.12932(3) 0.42568(2) 0.03134(10) Uani 1 1 d . . . . .
I22A I 0.4918(5) 0.2971(4) 0.2489(3) 0.0626(16) Uani 0.1439(17) 1 d . . P A 1
I23A I 0.3534(4) 0.3832(3) 0.2698(2) 0.0499(13) Uani 0.1439(17) 1 d . . P A 1
N15 N 0.4763(15) 0.3875(13) 0.3099(10) 0.025(3) Uani 0.326(3) 1 d . U P B 2
N16 N 0.7082(12) 0.4750(9) 0.3288(7) 0.044(2) Uani 0.530(3) 1 d D . P C 3
C41 C 0.3970(17) 0.3205(14) 0.2564(11) 0.024(2) Uani 0.326(3) 1 d . U P B 2
C42 C 0.3059(16) 0.2580(13) 0.2036(10) 0.024(3) Uani 0.326(3) 1 d . U P B 2
H42A H 0.311041 0.273429 0.159065 0.036 Uiso 0.326(3) 1 calc R U P B 2
H42B H 0.237939 0.259078 0.217247 0.036 Uiso 0.326(3) 1 calc R U P B 2
H42C H 0.303900 0.196953 0.196911 0.036 Uiso 0.326(3) 1 calc R U P B 2
C43 C 0.5951(13) 0.4176(10) 0.2907(9) 0.044(2) Uani 0.530(3) 1 d D U P C 3
C44 C 0.4766(14) 0.3554(12) 0.2848(10) 0.050(2) Uani 0.530(3) 1 d D U P C 3
H44A H 0.447316 0.309272 0.237931 0.076 Uiso 0.530(3) 1 calc R U P C 3
H44B H 0.432037 0.390994 0.290506 0.076 Uiso 0.530(3) 1 calc R U P C 3
H44C H 0.473212 0.325404 0.321984 0.076 Uiso 0.530(3) 1 calc R U P C 3
Fe1 Fe 0.57250(7) 0.82084(5) 0.23712(4) 0.01424(16) Uani 1 1 d . . . . .
N1 N 0.6335(4) 0.7362(3) 0.2141(3) 0.0167(10) Uani 1 1 d . . . . .
N2 N 0.6296(4) 0.8510(3) 0.1543(3) 0.0173(10) Uani 1 1 d . . . . .
N3 N 0.5365(4) 0.7589(3) 0.3112(3) 0.0176(10) Uani 1 1 d . . . . .
N4 N 0.7275(4) 0.6723(3) 0.1400(3) 0.0194(10) Uani 1 1 d . . . . .
N5 N 0.6721(4) 0.6172(3) 0.2379(3) 0.0191(10) Uani 1 1 d . . . . .
N6 N 0.7728(5) 0.5048(4) 0.2117(3) 0.0268(12) Uani 1 1 d D . . . .
HN6 H 0.742(6) 0.506(5) 0.247(3) 0.032 Uiso 1 1 d D U . . .
N7 N 0.5100(4) 0.9032(3) 0.2630(3) 0.0165(10) Uani 1 1 d . . . . .
N8 N 0.7053(4) 0.9268(3) 0.3030(3) 0.0165(10) Uani 1 1 d . . . . .
N9 N 0.4186(4) 0.7473(3) 0.1781(3) 0.0174(10) Uani 1 1 d . . . . .
N10 N 0.3502(4) 0.9333(3) 0.2592(3) 0.0175(10) Uani 1 1 d . . . . .
N11 N 0.5280(4) 1.0460(3) 0.3316(3) 0.0176(10) Uani 1 1 d . . . . .
N12 N 0.4355(5) 1.1628(4) 0.3726(3) 0.0254(12) Uani 1 1 d D . . . .
HN12 H 0.505(3) 1.178(6) 0.390(4) 0.04(2) Uiso 1 1 d D . . . .
C1 C 0.6826(5) 0.7315(4) 0.1587(3) 0.0168(11) Uani 1 1 d . . . . .
C2 C 0.6818(5) 0.7998(4) 0.1239(3) 0.0189(12) Uani 1 1 d . . . . .
C3 C 0.6263(5) 0.9173(4) 0.1274(3) 0.0210(12) Uani 1 1 d . . . . .
H3 H 0.589708 0.953160 0.147593 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6745(5) 0.9354(5) 0.0711(3) 0.0256(14) Uani 1 1 d . . . . .
H4 H 0.670834 0.982927 0.053420 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7274(6) 0.8841(5) 0.0413(3) 0.0276(14) Uani 1 1 d . . . . .
H5 H 0.761543 0.896323 0.003226 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7307(5) 0.8138(4) 0.0673(3) 0.0214(12) Uani 1 1 d . . . . .
H6A H 0.765552 0.776559 0.046849 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6278(5) 0.6776(4) 0.2517(3) 0.0155(11) Uani 1 1 d . . . . .
C8 C 0.5692(5) 0.6895(4) 0.3079(3) 0.0176(11) Uani 1 1 d . . . . .
C9 C 0.4801(5) 0.7744(4) 0.3609(3) 0.0211(12) Uani 1 1 d . . . . .
H9 H 0.456648 0.822395 0.364173 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4546(5) 0.7231(5) 0.4077(3) 0.0256(13) Uani 1 1 d . . . . .
H10 H 0.414857 0.736323 0.442322 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4876(6) 0.6532(5) 0.4034(4) 0.0263(14) Uani 1 1 d . . . . .
H11 H 0.470429 0.617310 0.434788 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5466(5) 0.6353(4) 0.3525(3) 0.0212(12) Uani 1 1 d . . . . .
H12A H 0.570544 0.587531 0.348500 0.025 Uiso 1 1 calc R U . . .
C13 C 0.7210(5) 0.6189(4) 0.1822(3) 0.0199(12) Uani 1 1 d . . . . .
C14 C 0.7740(5) 0.5551(4) 0.1669(3) 0.0224(12) Uani 1 1 d . . . . .
C15 C 0.8206(6) 0.4464(5) 0.2043(4) 0.0305(15) Uani 1 1 d . . . . .
H15 H 0.816340 0.410942 0.235886 0.037 Uiso 1 1 calc R U . . .
C16 C 0.8763(6) 0.4378(5) 0.1506(4) 0.0318(15) Uani 1 1 d . . . . .
H16 H 0.911799 0.397219 0.145689 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8802(6) 0.4880(5) 0.1044(4) 0.0290(14) Uani 1 1 d . . . . .
H17 H 0.918097 0.482283 0.067157 0.035 Uiso 1 1 calc R U . . .
C18 C 0.8279(5) 0.5477(4) 0.1125(4) 0.0254(13) Uani 1 1 d . . . . .
H18 H 0.829681 0.582700 0.080731 0.031 Uiso 1 1 calc R U . . .
C19 C 0.5706(5) 0.9867(4) 0.3093(3) 0.0180(11) Uani 1 1 d . . . . .
C20 C 0.6869(5) 1.0030(4) 0.3310(3) 0.0179(11) Uani 1 1 d . . . . .
C21 C 0.8101(5) 0.9352(4) 0.3187(3) 0.0192(12) Uani 1 1 d . . . . .
H21 H 0.825117 0.883602 0.300778 0.023 Uiso 1 1 calc R U . . .
C22 C 0.8975(5) 1.0160(5) 0.3602(3) 0.0245(13) Uani 1 1 d . . . . .
H22 H 0.970719 1.019306 0.369814 0.029 Uiso 1 1 calc R U . . .
C23 C 0.8773(5) 1.0923(4) 0.3876(4) 0.0256(13) Uani 1 1 d . . . . .
H23 H 0.936378 1.148211 0.415833 0.031 Uiso 1 1 calc R U . . .
C24 C 0.7695(5) 1.0853(4) 0.3729(3) 0.0220(12) Uani 1 1 d . . . . .
H24 H 0.752964 1.136031 0.391307 0.026 Uiso 1 1 calc R U . . .
C25 C 0.4000(5) 0.8789(4) 0.2395(3) 0.0169(11) Uani 1 1 d . . . . .
C26 C 0.3457(5) 0.7867(4) 0.1898(3) 0.0174(11) Uani 1 1 d . . . . .
C27 C 0.3795(5) 0.6648(4) 0.1302(3) 0.0224(13) Uani 1 1 d . . . . .
H27 H 0.428970 0.636816 0.120570 0.027 Uiso 1 1 calc R U . . .
C28 C 0.2680(5) 0.6187(4) 0.0938(4) 0.0256(13) Uani 1 1 d . . . . .
H28 H 0.242596 0.560190 0.060007 0.031 Uiso 1 1 calc R U . . .
C29 C 0.1948(5) 0.6584(4) 0.1070(4) 0.0250(13) Uani 1 1 d . . . . .
H29 H 0.118671 0.627343 0.082994 0.030 Uiso 1 1 calc R U . . .
C30 C 0.2344(5) 0.7442(4) 0.1559(3) 0.0237(13) Uani 1 1 d . . . . .
H30 H 0.186062 0.773226 0.165995 0.028 Uiso 1 1 calc R U . . .
C31 C 0.4187(5) 1.0158(4) 0.3043(3) 0.0184(12) Uani 1 1 d . . . . .
C32 C 0.3689(5) 1.0805(4) 0.3254(3) 0.0210(12) Uani 1 1 d . . . . .
C33 C 0.3993(7) 1.2268(5) 0.3951(4) 0.0340(16) Uani 1 1 d . . . . .
H33 H 0.448834 1.284058 0.427831 0.041 Uiso 1 1 calc R U . . .
C34 C 0.2901(7) 1.2098(5) 0.3709(4) 0.0350(17) Uani 1 1 d . . . . .
H34 H 0.263431 1.254759 0.387803 0.042 Uiso 1 1 calc R U . . .
C35 C 0.2196(6) 1.1275(5) 0.3220(4) 0.0337(16) Uani 1 1 d . . . . .
H35 H 0.144504 1.115859 0.304335 0.040 Uiso 1 1 calc R U . . .
C36 C 0.2591(6) 1.0608(5) 0.2985(4) 0.0280(14) Uani 1 1 d . . . . .
H36 H 0.211504 1.003523 0.264854 0.034 Uiso 1 1 calc R U . . .
N13 N 0.0493(5) 0.4066(5) 0.0191(4) 0.0385(15) Uani 1 1 d . . . . .
C37 C 0.0622(6) 0.3524(6) 0.0401(4) 0.0398(18) Uani 1 1 d . . . . .
C38 C 0.0812(10) 0.2849(7) 0.0663(7) 0.082(4) Uani 1 1 d . . . . .
H38A H 0.043759 0.225520 0.029631 0.123 Uiso 1 1 calc R U . . .
H38B H 0.051644 0.281837 0.108959 0.123 Uiso 1 1 calc R U . . .
H38C H 0.161184 0.301122 0.078103 0.123 Uiso 1 1 calc R U . . .
N14 N 0.6612(5) 0.2729(4) 0.4391(4) 0.0374(14) Uani 1 1 d . . . . .
C39 C 0.7452(7) 0.3336(5) 0.4506(4) 0.0320(15) Uani 1 1 d . . . . .
C40 C 0.8517(7) 0.4113(5) 0.4669(4) 0.0384(17) Uani 1 1 d . . . . .
H40A H 0.865364 0.451194 0.515132 0.058 Uiso 1 1 calc R U . . .
H40B H 0.850844 0.445171 0.432687 0.058 Uiso 1 1 calc R U . . .
H40C H 0.910864 0.389843 0.463780 0.058 Uiso 1 1 calc R U . . .


_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
I1 I2 2.7570(7) . ?
I3 I4 3.1166(7) . ?
I4 I5 2.7890(8) . ?
I6 I7 2.9099(7) 2_665 ?
I6 I7 2.9099(7) . ?
I8 I9 2.7594(7) . ?
I10 I11 2.7677(7) . ?
I12 I13 2.9692(7) . ?
I13 I14 2.8639(6) . ?
I15 I16 3.1132(7) . ?
I16 I17 2.7827(6) . ?
I18 I19 2.7505(6) . ?
I20 I21 2.9123(5) 2_656 ?
I20 I21 2.9123(5) . ?
I22A I23A 2.735(6) . ?
N15 C41 1.34(3) . ?
N16 C43 1.44(2) . ?
C41 C42 1.38(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.502(16) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
Fe1 N1 1.865(5) . ?
Fe1 N2 1.982(5) . ?
Fe1 N3 1.990(5) . ?
Fe1 N7 1.856(5) . ?
Fe1 N8 1.996(5) . ?
Fe1 N9 1.990(5) . ?
N1 C1 1.346(7) . ?
N1 C7 1.346(7) . ?
N2 C2 1.367(8) . ?
N2 C3 1.343(8) . ?
N3 C8 1.367(7) . ?
N3 C9 1.342(8) . ?
N4 C1 1.334(7) . ?
N4 C13 1.343(8) . ?
N5 C7 1.333(7) . ?
N5 C13 1.348(8) . ?
N6 HN6 0.86(2) . ?
N6 C14 1.354(8) . ?
N6 C15 1.334(8) . ?
N7 C19 1.345(8) . ?
N7 C25 1.356(7) . ?
N8 C20 1.378(7) . ?
N8 C21 1.341(8) . ?
N9 C26 1.371(7) . ?
N9 C27 1.338(8) . ?
N10 C25 1.323(7) . ?
N10 C31 1.345(8) . ?
N11 C19 1.326(7) . ?
N11 C31 1.344(8) . ?
N12 HN12 0.86(2) . ?
N12 C32 1.353(9) . ?
N12 C33 1.329(9) . ?
C1 C2 1.463(8) . ?
C2 C6 1.386(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(9) . ?
C6 H6A 0.9500 . ?
C7 C8 1.453(8) . ?
C8 C12 1.384(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(9) . ?
C12 H12A 0.9500 . ?
C13 C14 1.472(8) . ?
C14 C18 1.372(9) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(10) . ?
C16 H16 0.9500 . ?
C16 C17 1.370(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.460(8) . ?
C20 C24 1.378(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.461(8) . ?
C26 C30 1.382(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.397(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.383(10) . ?
C29 H29 0.9500 . ?
C29 C30 1.385(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.468(8) . ?
C32 C36 1.382(9) . ?
C33 H33 0.9500 . ?
C33 C34 1.376(11) . ?
C34 H34 0.9500 . ?
C34 C35 1.377(11) . ?
C35 H35 0.9500 . ?
C35 C36 1.403(9) . ?
C36 H36 0.9500 . ?
N13 C37 1.136(10) . ?
C37 C38 1.428(12) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
N14 C39 1.144(10) . ?
C39 C40 1.454(11) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I5 I4 I3 174.91(2) . . ?
I7 I6 I7 180.00(2) 2_665 . ?
I14 I13 I12 177.40(2) . . ?
I17 I16 I15 179.21(2) . . ?
I21 I20 I21 180.0 2_656 . ?
N15 C41 C42 172(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N16 C43 C44 153.8(15) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N1 Fe1 N2 80.3(2) . . ?
N1 Fe1 N3 79.9(2) . . ?
N1 Fe1 N8 100.1(2) . . ?
N1 Fe1 N9 99.8(2) . . ?
N2 Fe1 N3 160.3(2) . . ?
N2 Fe1 N8 90.0(2) . . ?
N2 Fe1 N9 92.1(2) . . ?
N3 Fe1 N8 93.8(2) . . ?
N3 Fe1 N9 90.9(2) . . ?
N7 Fe1 N1 177.7(2) . . ?
N7 Fe1 N2 102.0(2) . . ?
N7 Fe1 N3 97.8(2) . . ?
N7 Fe1 N8 80.1(2) . . ?
N7 Fe1 N9 80.1(2) . . ?
N9 Fe1 N8 160.1(2) . . ?
C1 N1 Fe1 120.6(4) . . ?
C1 N1 C7 118.6(5) . . ?
C7 N1 Fe1 120.8(4) . . ?
C2 N2 Fe1 114.9(4) . . ?
C3 N2 Fe1 127.5(4) . . ?
C3 N2 C2 117.6(5) . . ?
C8 N3 Fe1 114.9(4) . . ?
C9 N3 Fe1 127.9(4) . . ?
C9 N3 C8 117.1(5) . . ?
C1 N4 C13 114.0(5) . . ?
C7 N5 C13 114.2(5) . . ?
C14 N6 HN6 125(5) . . ?
C15 N6 HN6 113(5) . . ?
C15 N6 C14 122.4(6) . . ?
C19 N7 Fe1 121.2(4) . . ?
C19 N7 C25 117.8(5) . . ?
C25 N7 Fe1 120.8(4) . . ?
C20 N8 Fe1 114.7(4) . . ?
C21 N8 Fe1 128.4(4) . . ?
C21 N8 C20 116.7(5) . . ?
C26 N9 Fe1 114.8(4) . . ?
C27 N9 Fe1 127.5(4) . . ?
C27 N9 C26 117.7(5) . . ?
C25 N10 C31 114.0(5) . . ?
C19 N11 C31 114.5(5) . . ?
C32 N12 HN12 122(6) . . ?
C33 N12 HN12 115(6) . . ?
C33 N12 C32 122.4(6) . . ?
N1 C1 C2 111.5(5) . . ?
N4 C1 N1 123.0(5) . . ?
N4 C1 C2 125.6(5) . . ?
N2 C2 C1 112.7(5) . . ?
N2 C2 C6 122.9(6) . . ?
C6 C2 C1 124.4(6) . . ?
N2 C3 H3 118.8 . . ?
N2 C3 C4 122.5(6) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
C2 C6 C5 118.2(6) . . ?
C2 C6 H6A 120.9 . . ?
C5 C6 H6A 120.9 . . ?
N1 C7 C8 111.7(5) . . ?
N5 C7 N1 122.7(5) . . ?
N5 C7 C8 125.6(5) . . ?
N3 C8 C7 112.7(5) . . ?
N3 C8 C12 123.4(5) . . ?
C12 C8 C7 123.8(5) . . ?
N3 C9 H9 118.6 . . ?
N3 C9 C10 122.8(6) . . ?
C10 C9 H9 118.6 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(6) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(6) . . ?
C12 C11 H11 120.3 . . ?
C8 C12 C11 117.9(6) . . ?
C8 C12 H12A 121.0 . . ?
C11 C12 H12A 121.0 . . ?
N4 C13 N5 127.5(5) . . ?
N4 C13 C14 116.9(5) . . ?
N5 C13 C14 115.6(5) . . ?
N6 C14 C13 117.0(6) . . ?
N6 C14 C18 119.3(6) . . ?
C18 C14 C13 123.6(6) . . ?
N6 C15 H15 120.0 . . ?
N6 C15 C16 119.9(7) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(6) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(6) . . ?
C18 C17 H17 120.2 . . ?
C14 C18 C17 119.2(6) . . ?
C14 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
N7 C19 C20 111.9(5) . . ?
N11 C19 N7 123.0(5) . . ?
N11 C19 C20 125.1(6) . . ?
N8 C20 C19 112.0(5) . . ?
N8 C20 C24 123.7(6) . . ?
C24 C20 C19 124.2(5) . . ?
N8 C21 H21 118.6 . . ?
N8 C21 C22 122.8(6) . . ?
C22 C21 H21 118.6 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(6) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.9(6) . . ?
C24 C23 H23 120.6 . . ?
C20 C24 C23 118.3(6) . . ?
C20 C24 H24 120.9 . . ?
C23 C24 H24 120.8 . . ?
N7 C25 C26 111.4(5) . . ?
N10 C25 N7 123.3(5) . . ?
N10 C25 C26 125.3(5) . . ?
N9 C26 C25 112.4(5) . . ?
N9 C26 C30 123.0(6) . . ?
C30 C26 C25 124.5(5) . . ?
N9 C27 H27 119.0 . . ?
N9 C27 C28 121.9(6) . . ?
C28 C27 H27 119.0 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.9(6) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 120.6 . . ?
C28 C29 C30 118.9(6) . . ?
C30 C29 H29 120.6 . . ?
C26 C30 C29 118.6(6) . . ?
C26 C30 H30 120.7 . . ?
C29 C30 H30 120.7 . . ?
N10 C31 C32 116.4(5) . . ?
N11 C31 N10 127.3(5) . . ?
N11 C31 C32 116.3(5) . . ?
N12 C32 C31 117.4(6) . . ?
N12 C32 C36 119.9(6) . . ?
C36 C32 C31 122.7(6) . . ?
N12 C33 H33 120.0 . . ?
N12 C33 C34 119.9(7) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.7(6) . . ?
C35 C34 H34 120.2 . . ?
C34 C35 H35 120.1 . . ?
C34 C35 C36 119.8(7) . . ?
C36 C35 H35 120.1 . . ?
C32 C36 C35 118.2(7) . . ?
C32 C36 H36 120.9 . . ?
C35 C36 H36 120.9 . . ?
N13 C37 C38 178.6(10) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N14 C39 C40 178.8(8) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C42 H42A I7 0.98 2.99 3.771(19) 137.9 2_665 yes
C42 H42B I9 0.98 3.31 4.16(2) 145.8 . yes
C42 H42C I4 0.98 3.34 4.18(2) 144.8 1_545 yes
N6 HN6 N16 0.86(2) 1.86(4) 2.661(14) 154(8) . yes
N12 HN12 N14 0.86(2) 2.03(5) 2.820(9) 151(8) 1_565 yes
C4 H4 I3 0.95 3.18 3.878(6) 131.4 2_675 yes
C9 H9 I20 0.95 3.30 3.993(6) 131.0 1_565 yes
C9 H9 I21 0.95 3.12 3.855(6) 135.6 1_565 yes
C9 H9 N7 0.95 2.69 3.163(8) 111.5 . yes
C10 H10 N14 0.95 2.68 3.567(9) 154.7 2_666 yes
C15 H15 I12 0.95 3.11 3.947(7) 148.3 1_655 yes
C18 H18 N13 0.95 2.70 3.331(10) 124.9 2_665 yes
C27 H27 I7 0.95 3.12 3.807(6) 130.3 2_665 yes
C34 H34 I13 0.95 3.04 3.961(7) 162.5 1_565 yes
C34 H34 I14 0.95 3.14 3.926(7) 140.8 1_565 yes
C36 H36 I17 0.95 2.90 3.771(7) 153.5 . yes
C38 H38A I3 0.98 2.99 3.776(11) 138.3 2_565 yes
C38 H38B I9 0.98 3.12 3.912(12) 139.2 . yes
C38 H38C I7 0.98 3.08 3.971(11) 151.5 2_665 yes
C40 H40A I13 0.98 3.04 3.888(8) 144.9 2_666 yes
C40 H40C I12 0.98 3.27 3.752(8) 112.5 1_655 yes
C40 H40C I15 0.98 3.32 3.967(9) 125.6 2_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 N1 C1 N4 179.9(4) . . . . ?
Fe1 N1 C1 C2 1.1(7) . . . . ?
Fe1 N1 C7 N5 -178.7(4) . . . . ?
Fe1 N1 C7 C8 1.0(7) . . . . ?
Fe1 N2 C2 C1 1.0(6) . . . . ?
Fe1 N2 C2 C6 -177.4(5) . . . . ?
Fe1 N2 C3 C4 176.5(5) . . . . ?
Fe1 N3 C8 C7 2.1(6) . . . . ?
Fe1 N3 C8 C12 -176.6(5) . . . . ?
Fe1 N3 C9 C10 176.4(5) . . . . ?
Fe1 N7 C19 N11 -176.9(4) . . . . ?
Fe1 N7 C19 C20 3.3(7) . . . . ?
Fe1 N7 C25 N10 176.4(4) . . . . ?
Fe1 N7 C25 C26 -4.2(6) . . . . ?
Fe1 N8 C20 C19 3.7(6) . . . . ?
Fe1 N8 C20 C24 -174.6(5) . . . . ?
Fe1 N8 C21 C22 173.5(5) . . . . ?
Fe1 N9 C26 C25 4.8(6) . . . . ?
Fe1 N9 C26 C30 -177.2(5) . . . . ?
Fe1 N9 C27 C28 177.7(5) . . . . ?
N1 C1 C2 N2 -1.3(7) . . . . ?
N1 C1 C2 C6 177.0(6) . . . . ?
N1 C7 C8 N3 -2.0(7) . . . . ?
N1 C7 C8 C12 176.7(6) . . . . ?
N2 Fe1 N1 C1 -0.5(4) . . . . ?
N2 Fe1 N1 C7 -179.5(5) . . . . ?
N2 Fe1 N7 C19 -88.9(5) . . . . ?
N2 Fe1 N7 C25 95.5(4) . . . . ?
N2 C2 C6 C5 0.8(9) . . . . ?
N2 C3 C4 C5 0.2(10) . . . . ?
N3 Fe1 N1 C1 179.1(5) . . . . ?
N3 Fe1 N1 C7 0.1(4) . . . . ?
N3 Fe1 N7 C19 91.5(5) . . . . ?
N3 Fe1 N7 C25 -84.1(4) . . . . ?
N3 C8 C12 C11 -0.2(9) . . . . ?
N3 C9 C10 C11 -0.3(10) . . . . ?
N4 C1 C2 N2 179.9(5) . . . . ?
N4 C1 C2 C6 -1.8(10) . . . . ?
N4 C13 C14 N6 176.5(6) . . . . ?
N4 C13 C14 C18 -0.4(9) . . . . ?
N5 C7 C8 N3 177.7(5) . . . . ?
N5 C7 C8 C12 -3.6(10) . . . . ?
N5 C13 C14 N6 -2.9(8) . . . . ?
N5 C13 C14 C18 -179.8(6) . . . . ?
N6 C14 C18 C17 0.2(10) . . . . ?
N6 C15 C16 C17 -1.3(11) . . . . ?
N7 C19 C20 N8 -4.4(7) . . . . ?
N7 C19 C20 C24 174.0(6) . . . . ?
N7 C25 C26 N9 -0.7(7) . . . . ?
N7 C25 C26 C30 -178.6(5) . . . . ?
N8 Fe1 N1 C1 -88.7(5) . . . . ?
N8 Fe1 N1 C7 92.3(5) . . . . ?
N8 Fe1 N7 C19 -1.0(4) . . . . ?
N8 Fe1 N7 C25 -176.6(5) . . . . ?
N8 C20 C24 C23 0.3(9) . . . . ?
N8 C21 C22 C23 0.5(10) . . . . ?
N9 Fe1 N1 C1 90.0(5) . . . . ?
N9 Fe1 N1 C7 -89.0(5) . . . . ?
N9 Fe1 N7 C19 -178.9(5) . . . . ?
N9 Fe1 N7 C25 5.5(4) . . . . ?
N9 C26 C30 C29 -1.2(9) . . . . ?
N9 C27 C28 C29 0.0(10) . . . . ?
N10 C25 C26 N9 178.7(5) . . . . ?
N10 C25 C26 C30 0.7(9) . . . . ?
N10 C31 C32 N12 177.9(5) . . . . ?
N10 C31 C32 C36 -2.9(9) . . . . ?
N11 C19 C20 N8 175.9(5) . . . . ?
N11 C19 C20 C24 -5.8(9) . . . . ?
N11 C31 C32 N12 -3.0(8) . . . . ?
N11 C31 C32 C36 176.2(6) . . . . ?
N12 C32 C36 C35 -0.8(10) . . . . ?
N12 C33 C34 C35 -1.7(11) . . . . ?
C1 N1 C7 N5 2.3(8) . . . . ?
C1 N1 C7 C8 -178.0(5) . . . . ?
C1 N4 C13 N5 2.3(9) . . . . ?
C1 N4 C13 C14 -177.0(5) . . . . ?
C1 C2 C6 C5 -177.4(6) . . . . ?
C2 N2 C3 C4 -0.7(9) . . . . ?
C3 N2 C2 C1 178.6(5) . . . . ?
C3 N2 C2 C6 0.2(9) . . . . ?
C3 C4 C5 C6 0.9(10) . . . . ?
C4 C5 C6 C2 -1.3(10) . . . . ?
C7 N1 C1 N4 -1.0(9) . . . . ?
C7 N1 C1 C2 -179.9(5) . . . . ?
C7 N5 C13 N4 -1.3(9) . . . . ?
C7 N5 C13 C14 178.1(5) . . . . ?
C7 C8 C12 C11 -178.8(6) . . . . ?
C8 N3 C9 C10 -0.1(9) . . . . ?
C9 N3 C8 C7 179.0(5) . . . . ?
C9 N3 C8 C12 0.4(9) . . . . ?
C9 C10 C11 C12 0.4(10) . . . . ?
C10 C11 C12 C8 -0.2(10) . . . . ?
C13 N4 C1 N1 -1.1(8) . . . . ?
C13 N4 C1 C2 177.6(6) . . . . ?
C13 N5 C7 N1 -1.2(8) . . . . ?
C13 N5 C7 C8 179.2(5) . . . . ?
C13 C14 C18 C17 177.0(6) . . . . ?
C14 N6 C15 C16 1.8(11) . . . . ?
C15 N6 C14 C13 -178.3(6) . . . . ?
C15 N6 C14 C18 -1.3(10) . . . . ?
C15 C16 C17 C18 0.3(11) . . . . ?
C16 C17 C18 C14 0.3(10) . . . . ?
C19 N7 C25 N10 0.6(8) . . . . ?
C19 N7 C25 C26 -180.0(5) . . . . ?
C19 N11 C31 N10 1.3(9) . . . . ?
C19 N11 C31 C32 -177.7(5) . . . . ?
C19 C20 C24 C23 -177.8(6) . . . . ?
C20 N8 C21 C22 -0.9(8) . . . . ?
C21 N8 C20 C19 178.9(5) . . . . ?
C21 N8 C20 C24 0.5(8) . . . . ?
C21 C22 C23 C24 0.3(10) . . . . ?
C22 C23 C24 C20 -0.7(9) . . . . ?
C25 N7 C19 N11 -1.2(8) . . . . ?
C25 N7 C19 C20 179.0(5) . . . . ?
C25 N10 C31 N11 -1.8(9) . . . . ?
C25 N10 C31 C32 177.2(5) . . . . ?
C25 C26 C30 C29 176.5(6) . . . . ?
C26 N9 C27 C28 -1.3(9) . . . . ?
C27 N9 C26 C25 -176.0(5) . . . . ?
C27 N9 C26 C30 1.9(8) . . . . ?
C27 C28 C29 C30 0.7(10) . . . . ?
C28 C29 C30 C26 -0.2(9) . . . . ?
C31 N10 C25 N7 0.8(8) . . . . ?
C31 N10 C25 C26 -178.5(5) . . . . ?
C31 N11 C19 N7 0.3(8) . . . . ?
C31 N11 C19 C20 -180.0(5) . . . . ?
C31 C32 C36 C35 -179.9(6) . . . . ?
C32 N12 C33 C34 0.8(11) . . . . ?
C33 N12 C32 C31 179.7(6) . . . . ?
C33 N12 C32 C36 0.5(10) . . . . ?
C33 C34 C35 C36 1.4(11) . . . . ?
C34 C35 C36 C32 -0.1(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT434_mo_d8_4596_20sep20_ajp4_0m_a 
;
PROBLEM: Short Inter HL..HL Contact I9       ..I12      .       3.22 Ang.  
RESPONSE: This contact represents an I...I halogen bond.
;
####################################################################### 
# 
# 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_mo_d8_5784_6mar22_ajp2_0m
_database_code_depnum_ccdc_archive 'CCDC 2182007'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Bi4 I14), 2(C12 H10 N4 S), 4(C2 H3 N)'
_chemical_formula_sum            'C32 H32 Bi8 I28 N12 S2'
_chemical_formula_weight         5873.85
_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'
S S 0.1246 0.1234 '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                   21.2030(12)
_cell_length_b                   11.4331(5)
_cell_length_c                   40.625(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.697(2)
_cell_angle_gamma                90
_cell_volume                     9847.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9246
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.170
_shelx_estimated_absorpt_T_min   0.137
_exptl_absorpt_coefficient_mu    23.093
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    3.962
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             9952
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.119
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            199003
_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         28.331
_diffrn_reflns_theta_min         1.850
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                20377
_reflns_number_total             24538
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         1.421
_refine_diff_density_min         -1.502
_refine_diff_density_rms         0.279
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     792
_refine_ls_number_reflns         24538
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+66.5860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0570
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 HN4-N4
 0.86 with sigma of 0.02
 HN1-N1
 0.86 with sigma of 0.02
 N8-HN8
 0.86 with sigma of 0.02
 N1-C5 \\sim N1-C4
 with sigma of 0.02
 C13-N7B \\sim C19-N7A
 with sigma of 0.02
 C13-S2A \\sim C19-S2B
 with sigma of 0.02
 C1-N3A \\sim C7-N3B
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
S2A \\sim N7A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
S1A \\sim N3A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
S1B \\sim N3B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
N7B \\sim S2B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
3. Others
 Sof(S1B)=Sof(N3B)=1-FVAR(1)
 Sof(S1A)=Sof(N3A)=FVAR(1)
 Sof(N7B)=Sof(S2B)=1-FVAR(2)
 Sof(S2A)=Sof(N7A)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 N5(HN5), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
 C24(H24)
4.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C30(H30A,H30B,H30C), C28(H28A,H28B,H28C), C32(H32A,H32B,
 H32C)
;
_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 0.41137(2) 0.25343(2) 0.68338(2) 0.01321(5) Uani 1 1 d . . . . .
Bi2 Bi 0.40631(2) 0.12285(2) 0.57590(2) 0.01232(5) Uani 1 1 d . . . . .
Bi3 Bi 0.39564(2) -0.03574(2) 0.47411(2) 0.01187(5) Uani 1 1 d . . . . .
Bi4 Bi 0.39165(2) -0.17939(2) 0.36662(2) 0.01274(5) Uani 1 1 d . . . . .
Bi5 Bi 0.09899(2) 0.26604(2) 0.31278(2) 0.01382(6) Uani 1 1 d . . . . .
Bi6 Bi 0.09830(2) 0.39439(2) 0.42178(2) 0.01190(5) Uani 1 1 d . . . . .
Bi7 Bi 0.10299(2) 0.54649(2) 0.52646(2) 0.01202(5) Uani 1 1 d . . . . .
Bi8 Bi 0.10425(2) 0.70232(2) 0.63304(2) 0.01243(5) Uani 1 1 d . . . . .
I1 I 0.37509(2) 0.12977(4) 0.74216(2) 0.01759(10) Uani 1 1 d . . . . .
I2 I 0.47109(3) 0.45133(4) 0.71479(2) 0.02124(11) Uani 1 1 d . . . . .
I3 I 0.29520(2) 0.37497(4) 0.66959(2) 0.02331(11) Uani 1 1 d . . . . .
I4 I 0.47465(2) 0.32780(4) 0.61036(2) 0.01374(9) Uani 1 1 d . . . . .
I5 I 0.35961(2) 0.02673(4) 0.63900(2) 0.02119(11) Uani 1 1 d . . . . .
I6 I 0.30020(2) 0.26792(4) 0.56036(2) 0.02166(11) Uani 1 1 d . . . . .
I7 I 0.46962(2) 0.18724(4) 0.50672(2) 0.01330(9) Uani 1 1 d . . . . .
I8 I 0.34823(2) -0.09974(4) 0.54382(2) 0.01758(10) Uani 1 1 d . . . . .
I9 I 0.28228(2) 0.09116(4) 0.46217(2) 0.02114(11) Uani 1 1 d . . . . .
I10 I 0.46201(2) 0.03925(4) 0.41037(2) 0.01339(9) Uani 1 1 d . . . . .
I11 I 0.34599(2) -0.25237(4) 0.44303(2) 0.01474(9) Uani 1 1 d . . . . .
I12 I 0.28163(2) -0.03414(4) 0.35956(2) 0.01779(10) Uani 1 1 d . . . . .
I13 I 0.45433(2) -0.09059(4) 0.30813(2) 0.01593(9) Uani 1 1 d . . . . .
I14 I 0.34304(2) -0.38814(4) 0.33647(2) 0.02414(11) Uani 1 1 d . . . . .
I15 I 0.03617(3) 0.39797(4) 0.26193(2) 0.02390(11) Uani 1 1 d . . . . .
I16 I 0.12316(2) 0.06192(4) 0.27370(2) 0.02435(11) Uani 1 1 d . . . . .
I17 I 0.21704(2) 0.38006(5) 0.30373(2) 0.02626(12) Uani 1 1 d . . . . .
I18 I 0.02669(2) 0.46826(4) 0.36098(2) 0.01277(9) Uani 1 1 d . . . . .
I19 I 0.14899(3) 0.18068(4) 0.39099(2) 0.02171(11) Uani 1 1 d . . . . .
I20 I 0.20180(2) 0.53842(4) 0.40284(2) 0.02036(10) Uani 1 1 d . . . . .
I21 I 0.15415(2) 0.32434(4) 0.49227(2) 0.01580(9) Uani 1 1 d . . . . .
I22 I 0.03061(2) 0.61183(4) 0.45846(2) 0.01245(9) Uani 1 1 d . . . . .
I23 I 0.21304(2) 0.67762(5) 0.51072(2) 0.02404(11) Uani 1 1 d . . . . .
I24 I 0.03349(2) 0.75696(4) 0.55734(2) 0.01473(9) Uani 1 1 d . . . . .
I25 I 0.15242(2) 0.46818(4) 0.59158(2) 0.01527(9) Uani 1 1 d . . . . .
I26 I 0.21265(2) 0.83993(4) 0.61762(2) 0.02260(11) Uani 1 1 d . . . . .
I27 I 0.15694(2) 0.59569(4) 0.69055(2) 0.02061(10) Uani 1 1 d . . . . .
I28 I 0.03967(2) 0.89093(4) 0.66885(2) 0.01919(10) Uani 1 1 d . . . . .
N1 N 1.1070(3) 0.4456(6) 0.03935(18) 0.0269(16) Uani 1 1 d D . . . .
HN1 H 1.115(4) 0.471(6) 0.0198(9) 0.02(2) Uiso 1 1 d D . . . .
N2 N 0.9980(3) 0.3008(5) 0.14017(17) 0.0183(14) Uani 1 1 d . . . . .
N4 N 0.8267(3) 0.2198(6) 0.22110(18) 0.0216(14) Uani 1 1 d D . . . .
HN4 H 0.795(3) 0.208(7) 0.2336(18) 0.026 Uiso 1 1 d D U . . .
C1 C 1.0593(4) 0.3041(6) 0.1307(2) 0.0218(17) Uani 1 1 d D . . . .
C2 C 1.0765(4) 0.3551(6) 0.0990(2) 0.0197(16) Uani 1 1 d . . . . .
C3 C 1.1400(4) 0.3667(7) 0.0901(2) 0.0246(18) Uani 1 1 d . . . . .
H3 H 1.172727 0.341942 0.104665 0.029 Uiso 1 1 calc R U . . .
C4 C 1.1544(4) 0.4142(7) 0.0600(2) 0.030(2) Uani 1 1 d D . . . .
H4A H 1.197148 0.424882 0.053862 0.036 Uiso 1 1 calc R U . . .
C5 C 1.0457(4) 0.4332(6) 0.0470(2) 0.0253(18) Uani 1 1 d D . . . .
H5 H 1.013815 0.454538 0.031558 0.030 Uiso 1 1 calc R U . . .
C6 C 1.0295(4) 0.3898(6) 0.0771(2) 0.0253(18) Uani 1 1 d . . . . .
H6 H 0.986341 0.383549 0.082943 0.030 Uiso 1 1 calc R U . . .
C7 C 0.9949(4) 0.2545(6) 0.1696(2) 0.0180(15) Uani 1 1 d D . . . .
C8 C 0.9356(3) 0.2391(6) 0.18760(19) 0.0181(16) Uani 1 1 d . . . . .
C9 C 0.8780(4) 0.2649(7) 0.1725(2) 0.0284(19) Uani 1 1 d . . . . .
H9 H 0.876487 0.289491 0.150165 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8240(4) 0.2546(7) 0.1899(2) 0.0224(17) Uani 1 1 d . . . . .
H10 H 0.784457 0.272313 0.179868 0.027 Uiso 1 1 calc R U . . .
C11 C 0.8812(4) 0.1908(7) 0.2366(2) 0.0247(18) Uani 1 1 d . . . . .
H11 H 0.880810 0.164556 0.258816 0.030 Uiso 1 1 calc R U . . .
C12 C 0.9372(4) 0.1995(6) 0.2202(2) 0.0213(17) Uani 1 1 d . . . . .
H12 H 0.975960 0.179131 0.230638 0.026 Uiso 1 1 calc R U . . .
S1A S 1.06832(13) 0.2155(3) 0.18414(7) 0.0219(8) Uani 0.848(9) 1 d . U P A 1
N3A N 1.1036(6) 0.2636(10) 0.1510(3) 0.0219(9) Uani 0.848(9) 1 d D U P A 1
S1B S 1.1039(9) 0.2281(13) 0.1582(4) 0.024(4) Uani 0.152(9) 1 d . U P A 2
N3B N 1.0452(19) 0.205(5) 0.1834(14) 0.022(7) Uani 0.152(9) 1 d D U P A 2
N5 N 0.6399(3) 0.2337(6) 0.28756(19) 0.0277(16) Uani 1 1 d . . . . .
HN5 H 0.675219 0.225190 0.276644 0.033 Uiso 1 1 calc R U . . .
N6 N 0.4738(3) 0.3258(5) 0.36999(17) 0.0213(14) Uani 1 1 d . . . . .
N8 N 0.3777(4) 0.4577(6) 0.47497(19) 0.0272(16) Uani 1 1 d D . . . .
HN8 H 0.369(4) 0.487(6) 0.4938(10) 0.02(2) Uiso 1 1 d D . . . .
C13 C 0.4723(4) 0.2748(6) 0.3395(2) 0.0223(17) Uani 1 1 d D . . . .
C14 C 0.5315(4) 0.2581(6) 0.3214(2) 0.0214(17) Uani 1 1 d . . . . .
C15 C 0.5888(4) 0.2887(8) 0.3358(2) 0.034(2) Uani 1 1 d . . . . .
H15 H 0.590345 0.318617 0.357620 0.040 Uiso 1 1 calc R U . . .
C16 C 0.6431(4) 0.2755(8) 0.3183(2) 0.034(2) Uani 1 1 d . . . . .
H16 H 0.682696 0.295938 0.327875 0.040 Uiso 1 1 calc R U . . .
C17 C 0.5857(4) 0.2041(7) 0.2726(2) 0.0287(19) Uani 1 1 d . . . . .
H17 H 0.585847 0.175306 0.250704 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5293(4) 0.2153(7) 0.2891(2) 0.0248(18) Uani 1 1 d . . . . .
H18 H 0.490358 0.194609 0.278885 0.030 Uiso 1 1 calc R U . . .
C19 C 0.4151(4) 0.3276(6) 0.3810(2) 0.0211(17) Uani 1 1 d D . . . .
C20 C 0.4014(3) 0.3738(6) 0.41380(19) 0.0169(15) Uani 1 1 d . . . . .
C21 C 0.4493(4) 0.4261(6) 0.4325(2) 0.0213(17) Uani 1 1 d . . . . .
H21 H 0.490866 0.432001 0.424187 0.026 Uiso 1 1 calc R U . . .
C22 C 0.4357(4) 0.4688(7) 0.4631(2) 0.0262(18) Uani 1 1 d . . . . .
H22 H 0.467620 0.506382 0.475834 0.031 Uiso 1 1 calc R U . . .
C23 C 0.3301(4) 0.4080(7) 0.4581(2) 0.030(2) Uani 1 1 d . . . . .
H23 H 0.289293 0.401605 0.467333 0.036 Uiso 1 1 calc R U . . .
C24 C 0.3421(4) 0.3666(7) 0.4271(2) 0.0272(19) Uani 1 1 d . . . . .
H24 H 0.308787 0.332340 0.414597 0.033 Uiso 1 1 calc R U . . .
S2A S 0.3988(4) 0.2359(13) 0.3291(3) 0.018(2) Uani 0.328(10) 1 d D U P B 3
N7A N 0.3698(14) 0.282(3) 0.3636(7) 0.018(2) Uani 0.328(10) 1 d D U P B 3
N7B N 0.4180(7) 0.237(2) 0.3275(6) 0.021(3) Uani 0.672(10) 1 d D U P B 4
S2B S 0.3620(2) 0.2678(3) 0.35387(10) 0.0247(11) Uani 0.672(10) 1 d D U P B 4
N9 N 1.1062(4) 0.5393(6) -0.02435(19) 0.0323(18) Uani 1 1 d . . . . .
C25 C 1.1297(4) 0.5861(7) -0.0451(2) 0.0227(17) Uani 1 1 d . . . . .
C26 C 1.1597(4) 0.6446(7) -0.0726(2) 0.0279(19) Uani 1 1 d . . . . .
H26A H 1.127325 0.671064 -0.088297 0.042 Uiso 1 1 calc R U . . .
H26B H 1.188293 0.590043 -0.083498 0.042 Uiso 1 1 calc R U . . .
H26C H 1.183695 0.712180 -0.064435 0.042 Uiso 1 1 calc R U . . .
N10 N 0.7570(3) 0.1140(6) 0.27642(19) 0.0287(16) Uani 1 1 d . . . . .
C29 C 0.7737(4) 0.0264(7) 0.2866(2) 0.0241(18) Uani 1 1 d . . . . .
C30 C 0.7986(4) -0.0832(8) 0.3006(3) 0.038(2) Uani 1 1 d . . . . .
H30A H 0.791961 -0.146989 0.284789 0.058 Uiso 1 1 calc R U . . .
H30B H 0.776558 -0.101056 0.321024 0.058 Uiso 1 1 calc R U . . .
H30C H 0.843813 -0.074507 0.305203 0.058 Uiso 1 1 calc R U . . .
N11 N 0.7147(3) 0.3534(6) 0.23762(17) 0.0236(15) Uani 1 1 d . . . . .
C27 C 0.7054(3) 0.4499(7) 0.2347(2) 0.0206(16) Uani 1 1 d . . . . .
C28 C 0.6942(4) 0.5758(6) 0.2314(2) 0.028(2) Uani 1 1 d . . . . .
H28A H 0.726334 0.610014 0.217157 0.043 Uiso 1 1 calc R U . . .
H28B H 0.696368 0.612754 0.253114 0.043 Uiso 1 1 calc R U . . .
H28C H 0.652303 0.588898 0.221563 0.043 Uiso 1 1 calc R U . . .
N12 N 0.4004(4) 0.5560(6) 0.53795(19) 0.0310(17) Uani 1 1 d . . . . .
C31 C 0.3700(4) 0.5704(6) 0.5602(2) 0.0208(16) Uani 1 1 d . . . . .
C32 C 0.3312(4) 0.5905(8) 0.5885(2) 0.0293(19) Uani 1 1 d . . . . .
H32A H 0.345243 0.539649 0.606598 0.044 Uiso 1 1 calc R U . . .
H32B H 0.287159 0.573039 0.582892 0.044 Uiso 1 1 calc R U . . .
H32C H 0.334933 0.672469 0.595325 0.044 Uiso 1 1 calc R U . . .


_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 2.8874(5) . ?
Bi1 I2 2.8829(6) . ?
Bi1 I3 2.8772(6) . ?
Bi1 I4 3.3795(5) . ?
Bi1 I5 3.3355(6) . ?
Bi1 I13 3.4161(5) 3_656 ?
Bi2 I4 3.0823(5) . ?
Bi2 I5 2.9700(6) . ?
Bi2 I6 2.8594(6) . ?
Bi2 I7 3.2147(5) . ?
Bi2 I8 3.1068(5) . ?
Bi2 I10 3.3917(5) 3_656 ?
Bi3 I7 3.2656(5) . ?
Bi3 I7 3.4226(5) 3_656 ?
Bi3 I8 3.1039(5) . ?
Bi3 I9 2.8440(6) . ?
Bi3 I10 3.0839(5) . ?
Bi3 I11 2.9673(5) . ?
Bi4 I4 3.4243(5) 3_656 ?
Bi4 I10 3.4010(5) . ?
Bi4 I11 3.3678(6) . ?
Bi4 I12 2.8750(5) . ?
Bi4 I13 2.9191(5) . ?
Bi4 I14 2.8686(6) . ?
Bi5 I15 2.8721(6) . ?
Bi5 I16 2.8722(5) . ?
Bi5 I17 2.8500(6) . ?
Bi5 I18 3.4061(5) . ?
Bi6 I18 3.0045(5) . ?
Bi6 I19 2.9534(5) . ?
Bi6 I20 2.8565(5) . ?
Bi6 I21 3.1880(6) . ?
Bi6 I22 3.2425(5) . ?
Bi6 I24 3.4029(5) 3_566 ?
Bi7 I21 3.0972(5) . ?
Bi7 I22 3.4232(5) 3_566 ?
Bi7 I22 3.2311(6) . ?
Bi7 I23 2.8526(5) . ?
Bi7 I24 3.0954(5) . ?
Bi7 I25 2.9719(6) . ?
Bi8 I18 3.4041(5) 3_566 ?
Bi8 I25 3.3298(5) . ?
Bi8 I26 2.8611(5) . ?
Bi8 I27 2.8512(6) . ?
Bi8 I28 2.9478(5) . ?
N1 HN1 0.86(2) . ?
N1 C4 1.351(10) . ?
N1 C5 1.347(9) . ?
N2 C1 1.359(10) . ?
N2 C7 1.309(10) . ?
N4 HN4 0.86(2) . ?
N4 C10 1.328(10) . ?
N4 C11 1.352(11) . ?
C1 C2 1.464(11) . ?
C1 N3A 1.326(14) . ?
C1 S1B 1.694(19) . ?
C2 C3 1.407(10) . ?
C2 C6 1.386(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(11) . ?
C4 H4A 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.366(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.475(10) . ?
C7 S1A 1.717(8) . ?
C7 N3B 1.32(2) . ?
C8 C9 1.391(11) . ?
C8 C12 1.399(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.360(11) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.373(11) . ?
C12 H12 0.9500 . ?
S1A N3A 1.643(11) . ?
S1B N3B 1.64(6) . ?
N5 HN5 0.8800 . ?
N5 C16 1.338(12) . ?
N5 C17 1.337(11) . ?
N6 C13 1.369(11) . ?
N6 C19 1.329(10) . ?
N8 HN8 0.86(2) . ?
N8 C22 1.334(11) . ?
N8 C23 1.339(12) . ?
C13 C14 1.474(11) . ?
C13 S2A 1.672(11) . ?
C13 N7B 1.316(18) . ?
C14 C15 1.386(12) . ?
C14 C18 1.401(12) . ?
C15 H15 0.9500 . ?
C15 C16 1.369(12) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.383(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.466(11) . ?
C19 N7A 1.30(2) . ?
C19 S2B 1.708(8) . ?
C20 C21 1.397(11) . ?
C20 C24 1.378(11) . ?
C21 H21 0.9500 . ?
C21 C22 1.367(11) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.371(12) . ?
C24 H24 0.9500 . ?
S2A N7A 1.62(3) . ?
N7B S2B 1.647(19) . ?
N9 C25 1.119(10) . ?
C25 C26 1.455(11) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N10 C29 1.138(10) . ?
C29 C30 1.471(12) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N11 C27 1.127(10) . ?
C27 C28 1.465(10) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N12 C31 1.130(10) . ?
C31 C32 1.439(11) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Bi1 I4 164.103(15) . . ?
I1 Bi1 I5 88.701(15) . . ?
I1 Bi1 I13 83.092(14) . 3_656 ?
I2 Bi1 I1 97.946(17) . . ?
I2 Bi1 I4 90.812(15) . . ?
I2 Bi1 I5 171.483(16) . . ?
I2 Bi1 I13 91.258(15) . 3_656 ?
I3 Bi1 I1 99.293(16) . . ?
I3 Bi1 I2 94.444(17) . . ?
I3 Bi1 I4 93.189(15) . . ?
I3 Bi1 I5 89.701(17) . . ?
I3 Bi1 I13 173.442(17) . 3_656 ?
I4 Bi1 I13 83.479(13) . 3_656 ?
I5 Bi1 I4 81.518(13) . . ?
I5 Bi1 I13 84.230(14) . 3_656 ?
I4 Bi2 I7 91.370(14) . . ?
I4 Bi2 I8 174.254(16) . . ?
I4 Bi2 I10 87.660(13) . 3_656 ?
I5 Bi2 I4 92.817(15) . . ?
I5 Bi2 I7 170.553(15) . . ?
I5 Bi2 I8 85.661(14) . . ?
I5 Bi2 I10 86.459(15) . 3_656 ?
I6 Bi2 I4 91.350(15) . . ?
I6 Bi2 I5 97.785(17) . . ?
I6 Bi2 I7 90.575(15) . . ?
I6 Bi2 I8 94.345(16) . . ?
I6 Bi2 I10 175.687(16) . 3_656 ?
I7 Bi2 I10 85.254(13) . 3_656 ?
I8 Bi2 I7 89.341(14) . . ?
I8 Bi2 I10 86.717(14) . 3_656 ?
I7 Bi3 I7 84.679(13) . 3_656 ?
I8 Bi3 I7 88.469(14) . . ?
I8 Bi3 I7 87.240(14) . 3_656 ?
I9 Bi3 I7 176.667(16) . 3_656 ?
I9 Bi3 I7 94.113(15) . . ?
I9 Bi3 I8 89.625(16) . . ?
I9 Bi3 I10 96.216(16) . . ?
I9 Bi3 I11 93.356(16) . . ?
I10 Bi3 I7 84.362(13) . . ?
I10 Bi3 I7 86.765(13) . 3_656 ?
I10 Bi3 I8 171.048(16) . . ?
I11 Bi3 I7 172.065(15) . . ?
I11 Bi3 I7 88.007(14) . 3_656 ?
I11 Bi3 I8 94.259(14) . . ?
I11 Bi3 I10 92.171(14) . . ?
I10 Bi4 I4 82.246(12) . 3_656 ?
I11 Bi4 I4 82.637(13) . 3_656 ?
I11 Bi4 I10 80.195(12) . . ?
I12 Bi4 I4 168.965(16) . 3_656 ?
I12 Bi4 I10 88.730(14) . . ?
I12 Bi4 I11 89.602(14) . . ?
I12 Bi4 I13 95.440(15) . . ?
I13 Bi4 I4 90.633(14) . 3_656 ?
I13 Bi4 I10 88.201(14) . . ?
I13 Bi4 I11 167.253(16) . . ?
I14 Bi4 I4 89.789(15) . 3_656 ?
I14 Bi4 I10 170.997(17) . . ?
I14 Bi4 I11 94.680(15) . . ?
I14 Bi4 I12 98.688(17) . . ?
I14 Bi4 I13 96.115(17) . . ?
I15 Bi5 I18 81.317(15) . . ?
I16 Bi5 I15 96.511(18) . . ?
I16 Bi5 I18 162.530(16) . . ?
I17 Bi5 I15 93.859(18) . . ?
I17 Bi5 I16 97.898(17) . . ?
I17 Bi5 I18 99.541(15) . . ?
I18 Bi6 I21 170.951(15) . . ?
I18 Bi6 I22 86.574(14) . . ?
I18 Bi6 I24 86.535(14) . 3_566 ?
I19 Bi6 I18 93.859(15) . . ?
I19 Bi6 I21 92.265(15) . . ?
I19 Bi6 I22 173.920(16) . . ?
I19 Bi6 I24 89.372(15) . 3_566 ?
I20 Bi6 I18 89.931(16) . . ?
I20 Bi6 I19 94.485(16) . . ?
I20 Bi6 I21 96.230(16) . . ?
I20 Bi6 I22 91.579(14) . . ?
I20 Bi6 I24 174.939(16) . 3_566 ?
I21 Bi6 I22 86.636(13) . . ?
I21 Bi6 I24 86.876(14) . 3_566 ?
I22 Bi6 I24 84.599(12) . 3_566 ?
I21 Bi7 I22 86.660(13) . 3_566 ?
I21 Bi7 I22 88.371(14) . . ?
I22 Bi7 I22 83.673(13) . 3_566 ?
I23 Bi7 I21 92.213(16) . . ?
I23 Bi7 I22 177.354(17) . 3_566 ?
I23 Bi7 I22 93.907(15) . . ?
I23 Bi7 I24 94.419(16) . . ?
I23 Bi7 I25 94.436(17) . . ?
I24 Bi7 I21 172.017(16) . . ?
I24 Bi7 I22 86.526(13) . 3_566 ?
I24 Bi7 I22 86.748(14) . . ?
I25 Bi7 I21 91.746(14) . . ?
I25 Bi7 I22 171.646(15) . . ?
I25 Bi7 I22 87.994(14) . 3_566 ?
I25 Bi7 I24 92.168(14) . . ?
I25 Bi8 I18 80.268(12) . 3_566 ?
I26 Bi8 I18 171.411(17) . 3_566 ?
I26 Bi8 I25 94.540(15) . . ?
I26 Bi8 I28 94.879(16) . . ?
I27 Bi8 I18 90.476(15) . 3_566 ?
I27 Bi8 I25 87.205(15) . . ?
I27 Bi8 I26 96.132(18) . . ?
I27 Bi8 I28 95.057(17) . . ?
I28 Bi8 I18 89.981(14) . 3_566 ?
I28 Bi8 I25 170.020(16) . . ?
Bi1 I4 Bi4 88.385(13) . 3_656 ?
Bi2 I4 Bi1 91.028(13) . . ?
Bi2 I4 Bi4 97.492(13) . 3_656 ?
Bi2 I5 Bi1 93.904(14) . . ?
Bi2 I7 Bi3 92.381(13) . 3_656 ?
Bi2 I7 Bi3 88.406(13) . . ?
Bi3 I7 Bi3 95.320(13) . 3_656 ?
Bi3 I8 Bi2 93.352(14) . . ?
Bi2 I10 Bi4 92.256(12) 3_656 . ?
Bi3 I10 Bi2 95.340(14) . 3_656 ?
Bi3 I10 Bi4 91.875(13) . . ?
Bi3 I11 Bi4 94.639(13) . . ?
Bi4 I13 Bi1 96.629(15) . 3_656 ?
Bi6 I18 Bi5 93.170(13) . . ?
Bi6 I18 Bi8 100.647(14) . 3_566 ?
Bi8 I18 Bi5 91.447(12) 3_566 . ?
Bi7 I21 Bi6 93.928(14) . . ?
Bi6 I22 Bi7 92.793(12) . 3_566 ?
Bi7 I22 Bi6 90.424(13) . . ?
Bi7 I22 Bi7 96.327(13) . 3_566 ?
Bi7 I24 Bi6 95.863(13) . 3_566 ?
Bi7 I25 Bi8 95.801(14) . . ?
C4 N1 HN1 120(5) . . ?
C5 N1 HN1 117(5) . . ?
C5 N1 C4 122.8(8) . . ?
C7 N2 C1 109.1(7) . . ?
C10 N4 HN4 126(6) . . ?
C10 N4 C11 123.0(7) . . ?
C11 N4 HN4 111(6) . . ?
N2 C1 C2 120.5(7) . . ?
N2 C1 S1B 109.2(8) . . ?
C2 C1 S1B 129.9(9) . . ?
N3A C1 N2 119.2(9) . . ?
N3A C1 C2 120.2(8) . . ?
C3 C2 C1 121.0(7) . . ?
C6 C2 C1 119.7(7) . . ?
C6 C2 C3 119.3(8) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(8) . . ?
C4 C3 H3 120.3 . . ?
N1 C4 C3 119.0(8) . . ?
N1 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
N1 C5 H5 120.0 . . ?
N1 C5 C6 120.0(8) . . ?
C6 C5 H5 120.0 . . ?
C2 C6 H6 120.3 . . ?
C5 C6 C2 119.4(8) . . ?
C5 C6 H6 120.3 . . ?
N2 C7 C8 123.6(7) . . ?
N2 C7 S1A 111.4(6) . . ?
N2 C7 N3B 121(3) . . ?
C8 C7 S1A 125.0(6) . . ?
N3B C7 C8 115(3) . . ?
C9 C8 C7 120.3(7) . . ?
C9 C8 C12 119.8(7) . . ?
C12 C8 C7 119.8(7) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.5(8) . . ?
C10 C9 H9 120.3 . . ?
N4 C10 C9 119.8(8) . . ?
N4 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N4 C11 H11 120.2 . . ?
N4 C11 C12 119.7(8) . . ?
C12 C11 H11 120.2 . . ?
C8 C12 H12 120.9 . . ?
C11 C12 C8 118.2(8) . . ?
C11 C12 H12 120.9 . . ?
N3A S1A C7 92.9(6) . . ?
C1 N3A S1A 107.4(9) . . ?
N3B S1B C1 94.0(16) . . ?
C7 N3B S1B 106(4) . . ?
C16 N5 HN5 118.4 . . ?
C17 N5 HN5 118.4 . . ?
C17 N5 C16 123.2(8) . . ?
C19 N6 C13 107.4(7) . . ?
C22 N8 HN8 120(6) . . ?
C22 N8 C23 123.2(8) . . ?
C23 N8 HN8 117(6) . . ?
N6 C13 C14 119.7(7) . . ?
N6 C13 S2A 110.7(7) . . ?
C14 C13 S2A 129.5(8) . . ?
N7B C13 N6 119.0(11) . . ?
N7B C13 C14 121.2(12) . . ?
C15 C14 C13 120.3(8) . . ?
C15 C14 C18 120.2(8) . . ?
C18 C14 C13 119.5(7) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.4(9) . . ?
C16 C15 H15 120.3 . . ?
N5 C16 C15 119.4(9) . . ?
N5 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
N5 C17 H17 120.0 . . ?
N5 C17 C18 120.0(8) . . ?
C18 C17 H17 120.0 . . ?
C14 C18 H18 121.1 . . ?
C17 C18 C14 117.8(8) . . ?
C17 C18 H18 121.1 . . ?
N6 C19 C20 120.5(7) . . ?
N6 C19 S2B 112.9(6) . . ?
C20 C19 S2B 126.5(6) . . ?
N7A C19 N6 120.1(16) . . ?
N7A C19 C20 119.2(16) . . ?
C21 C20 C19 120.0(7) . . ?
C24 C20 C19 121.8(7) . . ?
C24 C20 C21 118.2(7) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(8) . . ?
C22 C21 H21 120.4 . . ?
N8 C22 C21 120.1(8) . . ?
N8 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
N8 C23 H23 121.0 . . ?
N8 C23 C24 118.0(8) . . ?
C24 C23 H23 121.0 . . ?
C20 C24 H24 119.3 . . ?
C23 C24 C20 121.3(8) . . ?
C23 C24 H24 119.3 . . ?
N7A S2A C13 93.2(13) . . ?
C19 N7A S2A 108(2) . . ?
C13 N7B S2B 108.9(16) . . ?
N7B S2B C19 91.7(8) . . ?
N9 C25 C26 178.6(10) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N10 C29 C30 176.6(10) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N11 C27 C28 179.0(11) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N12 C31 C32 179.2(9) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C6 C2 -2.3(11) . . . . ?
N2 C1 C2 C3 175.3(7) . . . . ?
N2 C1 C2 C6 -6.4(11) . . . . ?
N2 C1 N3A S1A 0.9(11) . . . . ?
N2 C1 S1B N3B -6(2) . . . . ?
N2 C7 C8 C9 5.6(11) . . . . ?
N2 C7 C8 C12 -173.7(7) . . . . ?
N2 C7 S1A N3A 1.0(7) . . . . ?
N2 C7 N3B S1B 5(5) . . . . ?
N4 C11 C12 C8 0.3(11) . . . . ?
C1 N2 C7 C8 179.1(6) . . . . ?
C1 N2 C7 S1A -0.6(7) . . . . ?
C1 N2 C7 N3B -9(3) . . . . ?
C1 C2 C3 C4 179.5(7) . . . . ?
C1 C2 C6 C5 -177.4(7) . . . . ?
C1 S1B N3B C7 1(4) . . . . ?
C2 C1 N3A S1A 178.9(6) . . . . ?
C2 C1 S1B N3B -178(2) . . . . ?
C2 C3 C4 N1 -1.9(12) . . . . ?
C3 C2 C6 C5 0.9(11) . . . . ?
C4 N1 C5 C6 1.6(12) . . . . ?
C5 N1 C4 C3 0.6(12) . . . . ?
C6 C2 C3 C4 1.2(11) . . . . ?
C7 N2 C1 C2 -178.2(6) . . . . ?
C7 N2 C1 N3A -0.2(11) . . . . ?
C7 N2 C1 S1B 8.8(9) . . . . ?
C7 C8 C9 C10 -177.4(7) . . . . ?
C7 C8 C12 C11 177.3(7) . . . . ?
C7 S1A N3A C1 -1.0(8) . . . . ?
C8 C7 S1A N3A -178.7(7) . . . . ?
C8 C7 N3B S1B 177.1(18) . . . . ?
C8 C9 C10 N4 -0.2(12) . . . . ?
C9 C8 C12 C11 -2.0(11) . . . . ?
C10 N4 C11 C12 1.5(12) . . . . ?
C11 N4 C10 C9 -1.5(12) . . . . ?
C12 C8 C9 C10 2.0(12) . . . . ?
S1A C7 C8 C9 -174.8(6) . . . . ?
S1A C7 C8 C12 5.9(10) . . . . ?
N3A C1 C2 C3 -2.7(12) . . . . ?
N3A C1 C2 C6 175.6(8) . . . . ?
S1B C1 C2 C3 -13.3(13) . . . . ?
S1B C1 C2 C6 165.0(9) . . . . ?
N3B C7 C8 C9 -167(3) . . . . ?
N3B C7 C8 C12 14(3) . . . . ?
N5 C17 C18 C14 0.0(12) . . . . ?
N6 C13 C14 C15 2.9(11) . . . . ?
N6 C13 C14 C18 -174.5(7) . . . . ?
N6 C13 S2A N7A -1.1(15) . . . . ?
N6 C13 N7B S2B 1.8(19) . . . . ?
N6 C19 C20 C21 5.8(10) . . . . ?
N6 C19 C20 C24 -173.7(7) . . . . ?
N6 C19 N7A S2A -3(3) . . . . ?
N6 C19 S2B N7B 0.8(10) . . . . ?
N8 C23 C24 C20 1.1(12) . . . . ?
C13 N6 C19 C20 178.0(6) . . . . ?
C13 N6 C19 N7A 2.4(19) . . . . ?
C13 N6 C19 S2B 0.0(8) . . . . ?
C13 C14 C15 C16 -178.2(8) . . . . ?
C13 C14 C18 C17 178.1(7) . . . . ?
C13 S2A N7A C19 2(2) . . . . ?
C13 N7B S2B C19 -1.4(14) . . . . ?
C14 C13 S2A N7A 176.7(13) . . . . ?
C14 C13 N7B S2B 179.0(8) . . . . ?
C14 C15 C16 N5 0.2(13) . . . . ?
C15 C14 C18 C17 0.6(12) . . . . ?
C16 N5 C17 C18 -0.5(12) . . . . ?
C17 N5 C16 C15 0.4(13) . . . . ?
C18 C14 C15 C16 -0.7(13) . . . . ?
C19 N6 C13 C14 -178.4(6) . . . . ?
C19 N6 C13 S2A -0.4(9) . . . . ?
C19 N6 C13 N7B -1.2(14) . . . . ?
C19 C20 C21 C22 180.0(7) . . . . ?
C19 C20 C24 C23 178.6(7) . . . . ?
C20 C19 N7A S2A -178.9(11) . . . . ?
C20 C19 S2B N7B -177.0(10) . . . . ?
C20 C21 C22 N8 1.6(11) . . . . ?
C21 C20 C24 C23 -0.9(11) . . . . ?
C22 N8 C23 C24 0.1(12) . . . . ?
C23 N8 C22 C21 -1.4(12) . . . . ?
C24 C20 C21 C22 -0.5(11) . . . . ?
S2A C13 C14 C15 -174.7(9) . . . . ?
S2A C13 C14 C18 7.9(13) . . . . ?
N7A C19 C20 C21 -178.5(17) . . . . ?
N7A C19 C20 C24 1.9(19) . . . . ?
N7B C13 C14 C15 -174.2(13) . . . . ?
N7B C13 C14 C18 8.3(16) . . . . ?
S2B C19 C20 C21 -176.5(6) . . . . ?
S2B C19 C20 C24 4.0(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_mo_d8_4091_18feb20_ajp1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2182002'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(I3), C12 H10 N4 S, C12 H8 N4 S'
_chemical_formula_sum            'C24 H18 I6 N8 S2'
_chemical_formula_weight         1243.98
_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'
S S 0.1246 0.1234 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7763(6)
_cell_length_b                   25.918(2)
_cell_length_c                   17.0369(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.309(3)
_cell_angle_gamma                90
_cell_volume                     3388.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9328
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.560
_shelx_estimated_absorpt_T_min   0.160
_exptl_absorpt_coefficient_mu    5.653
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.438
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.116
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            52923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         2.423
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6369
_reflns_number_total             6943
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6943
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0217
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0149P)²+6.1469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0531
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 S1A-N3A \\sim S1B-N3B
 with sigma of 0.01
 C1-S1B \\sim C7-S1A
 with sigma of 0.01
 C13-N7A \\sim C19-N7B
 with sigma of 0.01
 C13-S2B \\sim C19-S2A
 with sigma of 0.01
 S2A-N7A \\sim S2B-N7B
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
S1A \\sim N3A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C19 \\sim N7B: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C13 \\sim S2B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
3. Others
 Sof(S1B)=Sof(N3B)=1-FVAR(1)
 Sof(S1A)=Sof(N3A)=FVAR(1)
 Sof(S2B)=Sof(N7B)=1-FVAR(2)
 Sof(S2A)=Sof(N7A)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.94430(3) 0.28985(2) 0.30719(2) 0.02808(6) Uani 1 1 d . . . . .
I2 I 0.76135(3) 0.24877(2) 0.42948(2) 0.02329(6) Uani 1 1 d . . . . .
I3 I 0.53705(3) 0.21588(2) 0.54450(2) 0.02960(6) Uani 1 1 d . . . . .
I4 I 0.10180(3) 0.43631(2) 0.21829(2) 0.02675(6) Uani 1 1 d . . . . .
I5 I 0.24575(3) 0.54030(2) 0.20137(2) 0.02285(6) Uani 1 1 d . . . . .
I6 I 0.35368(3) 0.64672(2) 0.18303(2) 0.02797(6) Uani 1 1 d . . . . .
N1 N 0.4448(4) 0.33971(12) 0.31241(16) 0.0190(6) Uani 1 1 d . . . . .
N2 N 0.6096(4) 0.43212(11) 0.13996(15) 0.0185(6) Uani 1 1 d . . . . .
N4 N 0.8050(4) 0.58288(11) 0.14998(16) 0.0193(6) Uani 1 1 d . . . . .
C1 C 0.5702(4) 0.38312(13) 0.12372(17) 0.0169(6) Uani 1 1 d D . . . .
C2 C 0.5092(4) 0.34925(14) 0.18265(18) 0.0182(7) Uani 1 1 d . . . . .
C3 C 0.4998(4) 0.36906(13) 0.25734(18) 0.0181(6) Uani 1 1 d . . . . .
H3 H 0.532872 0.403820 0.269342 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3965(4) 0.29036(14) 0.2985(2) 0.0216(7) Uani 1 1 d . . . . .
H4A H 0.357469 0.270512 0.339096 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4038(4) 0.26856(14) 0.2254(2) 0.0229(7) Uani 1 1 d . . . . .
H5 H 0.370228 0.233655 0.215145 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4607(4) 0.29834(14) 0.16712(19) 0.0220(7) Uani 1 1 d . . . . .
H6 H 0.466579 0.283823 0.116415 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6645(4) 0.45316(13) 0.07615(18) 0.0190(7) Uani 1 1 d D . . . .
C8 C 0.7268(4) 0.50680(13) 0.07711(19) 0.0189(7) Uani 1 1 d . . . . .
C9 C 0.7398(4) 0.53496(13) 0.14685(19) 0.0189(7) Uani 1 1 d . . . . .
H9 H 0.702623 0.520321 0.192409 0.023 Uiso 1 1 calc R U . . .
C10 C 0.8601(5) 0.60533(13) 0.08749(19) 0.0216(7) Uani 1 1 d . . . . .
H10 H 0.908176 0.639093 0.092335 0.026 Uiso 1 1 calc R U . . .
C11 C 0.8465(5) 0.57917(14) 0.0162(2) 0.0256(8) Uani 1 1 d . . . . .
H11 H 0.882253 0.595079 -0.028723 0.031 Uiso 1 1 calc R U . . .
C12 C 0.7806(5) 0.52978(14) 0.0109(2) 0.0249(7) Uani 1 1 d . . . . .
H12 H 0.771636 0.511313 -0.037754 0.030 Uiso 1 1 calc R U . . .
HN1 H 0.439(6) 0.3526(17) 0.356(3) 0.030 Uiso 1 1 d . U . . .
HN4 H 0.820(5) 0.6008(17) 0.193(3) 0.030 Uiso 1 1 d . U . . .
S1A S 0.6763(13) 0.4093(3) 0.0051(5) 0.0229(15) Uani 0.279(6) 1 d D U P A 1
N3A N 0.600(3) 0.3620(8) 0.0556(11) 0.024(4) Uani 0.279(6) 1 d D U P A 1
S1B S 0.5963(3) 0.36669(10) 0.02955(11) 0.0242(5) Uani 0.721(6) 1 d D . P A 2
N3B N 0.6629(15) 0.4254(3) 0.0092(7) 0.0193(18) Uani 0.721(6) 1 d D . P A 2
N5 N 0.4385(4) 0.38956(11) 0.45171(15) 0.0179(5) Uani 1 1 d . . . . .
N6 N 0.1732(3) 0.52979(10) 0.47054(15) 0.0156(5) Uani 1 1 d . . . . .
N8 N -0.1301(4) 0.62428(11) 0.29886(15) 0.0188(6) Uani 1 1 d . . . . .
C13 C 0.2538(4) 0.50518(13) 0.53726(17) 0.0163(6) Uani 1 1 d D U . . .
C14 C 0.3522(4) 0.45770(12) 0.53207(18) 0.0152(6) Uani 1 1 d . . . . .
C15 C 0.3530(4) 0.43351(13) 0.45856(18) 0.0170(6) Uani 1 1 d . . . . .
H15 H 0.290528 0.448980 0.411961 0.020 Uiso 1 1 calc R U . . .
C16 C 0.5270(4) 0.36800(13) 0.51752(19) 0.0194(7) Uani 1 1 d . . . . .
H16 H 0.587678 0.336668 0.512520 0.023 Uiso 1 1 calc R U . . .
C17 C 0.5341(4) 0.38927(13) 0.59241(19) 0.0205(7) Uani 1 1 d . . . . .
H17 H 0.598884 0.372978 0.637732 0.025 Uiso 1 1 calc R U . . .
C18 C 0.4453(4) 0.43462(13) 0.60004(19) 0.0183(6) Uani 1 1 d . . . . .
H18 H 0.447537 0.449943 0.650849 0.022 Uiso 1 1 calc R U . . .
C19 C 0.0944(4) 0.57137(13) 0.49193(17) 0.0162(6) Uani 1 1 d D U . . .
C20 C -0.0050(4) 0.60710(12) 0.43497(18) 0.0156(6) Uani 1 1 d . . . . .
C21 C -0.0355(4) 0.59429(13) 0.35372(18) 0.0185(6) Uani 1 1 d . . . . .
H21 H 0.012730 0.563240 0.337104 0.022 Uiso 1 1 calc R U . . .
C22 C -0.1953(4) 0.66838(13) 0.3226(2) 0.0220(7) Uani 1 1 d . . . . .
H22 H -0.262107 0.689721 0.283744 0.026 Uiso 1 1 calc R U . . .
C23 C -0.1697(4) 0.68418(13) 0.4010(2) 0.0223(7) Uani 1 1 d . . . . .
H23 H -0.216548 0.715970 0.415571 0.027 Uiso 1 1 calc R U . . .
C24 C -0.0748(4) 0.65301(13) 0.45793(19) 0.0192(7) Uani 1 1 d . . . . .
H24 H -0.057358 0.662861 0.512352 0.023 Uiso 1 1 calc R U . . .
S2A S 0.12272(14) 0.57821(5) 0.59377(6) 0.0195(3) Uani 0.890(4) 1 d D . P B 3
N7A N 0.2422(6) 0.52571(19) 0.6085(3) 0.0176(9) Uani 0.890(4) 1 d D . P B 3
S2B S 0.2056(17) 0.5352(5) 0.6179(6) 0.0165(13) Uani 0.110(4) 1 d D U P B 4
N7B N 0.090(4) 0.5812(10) 0.5684(6) 0.018(4) Uani 0.110(4) 1 d D U P B 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
I1 I2 2.9082(4) . ?
I2 I3 2.9521(4) . ?
I4 I5 2.9503(4) . ?
I5 I6 2.9145(4) . ?
N1 C3 1.331(4) . ?
N1 C4 1.343(5) . ?
N1 HN1 0.82(4) . ?
N2 C1 1.325(4) . ?
N2 C7 1.346(4) . ?
N4 C9 1.339(4) . ?
N4 C10 1.343(4) . ?
N4 HN4 0.86(4) . ?
C1 C2 1.469(5) . ?
C1 N3A 1.34(2) . ?
C1 S1B 1.704(3) . ?
C2 C3 1.385(4) . ?
C2 C6 1.386(5) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9500 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.471(5) . ?
C7 S1A 1.674(7) . ?
C7 N3B 1.347(11) . ?
C8 C9 1.384(5) . ?
C8 C12 1.398(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.380(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(5) . ?
C12 H12 0.9500 . ?
S1A N3A 1.661(10) . ?
S1B N3B 1.661(7) . ?
N5 C15 1.333(4) . ?
N5 C16 1.339(4) . ?
N6 C13 1.364(4) . ?
N6 C19 1.319(4) . ?
N8 C21 1.340(4) . ?
N8 C22 1.339(5) . ?
C13 C14 1.459(5) . ?
C13 N7A 1.342(6) . ?
C13 S2B 1.674(8) . ?
C14 C15 1.401(4) . ?
C14 C18 1.397(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.383(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.468(4) . ?
C19 S2A 1.722(3) . ?
C19 N7B 1.334(11) . ?
C20 C21 1.406(4) . ?
C20 C24 1.390(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.381(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(5) . ?
C24 H24 0.9500 . ?
S2A N7A 1.644(4) . ?
S2B N7B 1.640(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
I1 I2 I3 172.443(11) . . ?
I6 I5 I4 174.485(10) . . ?
C3 N1 C4 122.2(3) . . ?
C3 N1 HN1 118(3) . . ?
C4 N1 HN1 119(3) . . ?
C1 N2 C7 108.2(3) . . ?
C9 N4 C10 122.5(3) . . ?
C9 N4 HN4 122(3) . . ?
C10 N4 HN4 115(3) . . ?
N2 C1 C2 121.3(3) . . ?
N2 C1 N3A 120.4(7) . . ?
N2 C1 S1B 112.2(3) . . ?
C2 C1 S1B 126.5(3) . . ?
N3A C1 C2 118.0(7) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 C6 118.4(3) . . ?
C6 C2 C1 123.1(3) . . ?
N1 C3 C2 120.4(3) . . ?
N1 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
N1 C4 H4A 120.0 . . ?
N1 C4 C5 119.9(3) . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C2 C6 C5 120.1(3) . . ?
C2 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N2 C7 C8 121.4(3) . . ?
N2 C7 S1A 111.7(4) . . ?
N2 C7 N3B 120.4(5) . . ?
C8 C7 S1A 126.4(4) . . ?
N3B C7 C8 118.2(5) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 C12 118.5(3) . . ?
C12 C8 C7 122.3(3) . . ?
N4 C9 C8 119.9(3) . . ?
N4 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N4 C10 H10 120.1 . . ?
N4 C10 C11 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.3(3) . . ?
C12 C11 H11 120.3 . . ?
C8 C12 H12 120.0 . . ?
C11 C12 C8 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
N3A S1A C7 93.5(10) . . ?
C1 N3A S1A 105.9(14) . . ?
N3B S1B C1 93.2(4) . . ?
C7 N3B S1B 105.8(7) . . ?
C15 N5 C16 118.6(3) . . ?
C19 N6 C13 108.8(3) . . ?
C22 N8 C21 118.5(3) . . ?
N6 C13 C14 121.2(3) . . ?
N6 C13 S2B 109.5(5) . . ?
C14 C13 S2B 129.1(5) . . ?
N7A C13 N6 118.7(3) . . ?
N7A C13 C14 120.1(3) . . ?
C15 C14 C13 120.6(3) . . ?
C18 C14 C13 121.2(3) . . ?
C18 C14 C15 118.2(3) . . ?
N5 C15 C14 122.3(3) . . ?
N5 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
N5 C16 H16 118.5 . . ?
N5 C16 C17 123.0(3) . . ?
C17 C16 H16 118.5 . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.7(3) . . ?
C18 C17 H17 120.6 . . ?
C14 C18 H18 120.4 . . ?
C17 C18 C14 119.1(3) . . ?
C17 C18 H18 120.4 . . ?
N6 C19 C20 123.4(3) . . ?
N6 C19 S2A 111.9(2) . . ?
N6 C19 N7B 120.7(8) . . ?
C20 C19 S2A 124.7(2) . . ?
N7B C19 C20 115.6(8) . . ?
C21 C20 C19 119.3(3) . . ?
C24 C20 C19 122.8(3) . . ?
C24 C20 C21 117.9(3) . . ?
N8 C21 C20 122.4(3) . . ?
N8 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
N8 C22 H22 118.6 . . ?
N8 C22 C23 122.9(3) . . ?
C23 C22 H22 118.6 . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.9(3) . . ?
C24 C23 H23 120.6 . . ?
C20 C24 H24 120.3 . . ?
C23 C24 C20 119.5(3) . . ?
C23 C24 H24 120.3 . . ?
N7A S2A C19 92.6(2) . . ?
C13 N7A S2A 108.0(3) . . ?
N7B S2B C13 95.3(9) . . ?
C19 N7B S2B 105.5(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 I2 0.95 3.13 3.835(3) 132.4 2_655 yes
C10 H10 I3 0.95 3.15 3.806(3) 128.1 2_655 yes
C11 H11 I3 0.95 3.21 3.840(4) 125.2 2_655 yes
N1 HN1 N5 0.82(4) 1.89(5) 2.710(4) 173(4) . yes
N4 HN4 N8 0.86(4) 1.88(4) 2.725(4) 166(4) 1_655 yes
C16 H16 I2 0.95 3.10 4.001(3) 158.0 . yes
C16 H16 I3 0.95 3.21 3.969(3) 137.9 . yes
C17 H17 I6 0.95 3.06 3.897(3) 148.0 3_666 yes
C21 H21 I5 0.95 3.22 3.913(3) 131.8 . yes
C22 H22 I1 0.95 3.23 4.143(3) 161.8 2 yes
C23 H23 I3 0.95 3.22 4.073(3) 151.0 3_566 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 C6 -0.2(5) . . . . ?
N2 C1 C2 C3 -2.5(5) . . . . ?
N2 C1 C2 C6 177.6(3) . . . . ?
N2 C1 N3A S1A -3.2(18) . . . . ?
N2 C1 S1B N3B 0.4(5) . . . . ?
N2 C7 C8 C9 4.3(5) . . . . ?
N2 C7 C8 C12 -178.5(3) . . . . ?
N2 C7 S1A N3A 2.4(10) . . . . ?
N2 C7 N3B S1B -3.2(9) . . . . ?
N4 C10 C11 C12 -1.7(5) . . . . ?
C1 N2 C7 C8 -176.8(3) . . . . ?
C1 N2 C7 S1A -4.3(5) . . . . ?
C1 N2 C7 N3B 3.5(7) . . . . ?
C1 C2 C3 N1 179.8(3) . . . . ?
C1 C2 C6 C5 -179.8(3) . . . . ?
C1 S1B N3B C7 1.4(7) . . . . ?
C2 C1 N3A S1A -177.2(7) . . . . ?
C2 C1 S1B N3B 179.5(5) . . . . ?
C3 N1 C4 C5 0.2(5) . . . . ?
C3 C2 C6 C5 0.3(5) . . . . ?
C4 N1 C3 C2 0.0(5) . . . . ?
C4 C5 C6 C2 -0.1(5) . . . . ?
C6 C2 C3 N1 -0.3(5) . . . . ?
C7 N2 C1 C2 178.8(3) . . . . ?
C7 N2 C1 N3A 5.0(12) . . . . ?
C7 N2 C1 S1B -2.1(3) . . . . ?
C7 C8 C9 N4 176.4(3) . . . . ?
C7 C8 C12 C11 -176.5(3) . . . . ?
C7 S1A N3A C1 0.3(14) . . . . ?
C8 C7 S1A N3A 174.4(9) . . . . ?
C8 C7 N3B S1B 177.2(4) . . . . ?
C9 N4 C10 C11 1.5(5) . . . . ?
C9 C8 C12 C11 0.7(5) . . . . ?
C10 N4 C9 C8 -0.3(5) . . . . ?
C10 C11 C12 C8 0.6(5) . . . . ?
C12 C8 C9 N4 -0.8(5) . . . . ?
S1A C7 C8 C9 -167.0(5) . . . . ?
S1A C7 C8 C12 10.2(6) . . . . ?
N3A C1 C2 C3 171.5(12) . . . . ?
N3A C1 C2 C6 -8.4(12) . . . . ?
S1B C1 C2 C3 178.5(3) . . . . ?
S1B C1 C2 C6 -1.4(5) . . . . ?
N3B C7 C8 C9 -176.0(6) . . . . ?
N3B C7 C8 C12 1.2(7) . . . . ?
N5 C16 C17 C18 0.4(5) . . . . ?
N6 C13 C14 C15 -5.9(5) . . . . ?
N6 C13 C14 C18 175.2(3) . . . . ?
N6 C13 N7A S2A 0.8(5) . . . . ?
N6 C13 S2B N7B -2.6(15) . . . . ?
N6 C19 C20 C21 7.2(5) . . . . ?
N6 C19 C20 C24 -174.4(3) . . . . ?
N6 C19 S2A N7A 0.6(3) . . . . ?
N6 C19 N7B S2B 3(3) . . . . ?
N8 C22 C23 C24 -0.9(5) . . . . ?
C13 N6 C19 C20 179.8(3) . . . . ?
C13 N6 C19 S2A -0.2(3) . . . . ?
C13 N6 C19 N7B -5(2) . . . . ?
C13 C14 C15 N5 -178.6(3) . . . . ?
C13 C14 C18 C17 178.9(3) . . . . ?
C13 S2B N7B C19 0(2) . . . . ?
C14 C13 N7A S2A -179.6(3) . . . . ?
C14 C13 S2B N7B -177.6(14) . . . . ?
C15 N5 C16 C17 -0.1(5) . . . . ?
C15 C14 C18 C17 0.0(5) . . . . ?
C16 N5 C15 C14 -0.3(5) . . . . ?
C16 C17 C18 C14 -0.4(5) . . . . ?
C18 C14 C15 N5 0.3(5) . . . . ?
C19 N6 C13 C14 -179.9(3) . . . . ?
C19 N6 C13 N7A -0.4(4) . . . . ?
C19 N6 C13 S2B 4.6(6) . . . . ?
C19 C20 C21 N8 177.7(3) . . . . ?
C19 C20 C24 C23 -178.8(3) . . . . ?
C19 S2A N7A C13 -0.8(3) . . . . ?
C20 C19 S2A N7A -179.5(3) . . . . ?
C20 C19 N7B S2B 178.5(12) . . . . ?
C21 N8 C22 C23 -0.2(5) . . . . ?
C21 C20 C24 C23 -0.3(5) . . . . ?
C22 N8 C21 C20 1.0(5) . . . . ?
C22 C23 C24 C20 1.1(5) . . . . ?
C24 C20 C21 N8 -0.8(5) . . . . ?
S2A C19 C20 C21 -172.8(2) . . . . ?
S2A C19 C20 C24 5.7(4) . . . . ?
N7A C13 C14 C15 174.5(4) . . . . ?
N7A C13 C14 C18 -4.3(5) . . . . ?
S2B C13 C14 C15 168.5(6) . . . . ?
S2B C13 C14 C18 -10.3(7) . . . . ?
N7B C19 C20 C21 -167.9(19) . . . . ?
N7B C19 C20 C24 10.6(19) . . . . ?

_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_mo_d8_5786_6mar22_ajp4_0m
_database_code_depnum_ccdc_archive 'CCDC 2182010'
loop_
_audit_author_name
_audit_author_address
'Andrew Peloquin'
;United States Air Force Academy
United States of America
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi6 I22, 2(C12 H10 N4 S), 2(C H4 O)'
_chemical_formula_sum            'C26 H28 Bi6 I22 N8 O2 S2'
_chemical_formula_weight         4594.36
_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'
S S 0.1246 0.1234 '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                   14.9488(11)
_cell_length_b                   10.7020(7)
_cell_length_c                   25.0852(19)
_cell_angle_alpha                90
_cell_angle_beta                 106.469(3)
_cell_angle_gamma                90
_cell_volume                     3848.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9236
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.124
_shelx_estimated_absorpt_T_min   0.061
_exptl_absorpt_coefficient_mu    22.578
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_absorpt_special_details   .
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    3.965
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3904
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.159
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            136509
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         2.083
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8179
_reflns_number_total             9610
_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 (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.824
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.203
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         9610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0210
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0126P)²+3.9803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0409
_refine_ls_wR_factor_ref         0.0427
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N4(HN4), C3(H3), C4(H1), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
1.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.75670(2) 0.49877(2) 0.73498(2) 0.01170(4) Uani 1 1 d . . . . .
Bi2 Bi 0.48772(2) 0.50740(2) 0.59546(2) 0.01138(4) Uani 1 1 d . . . . .
Bi3 Bi 0.22367(2) 0.49283(2) 0.45264(2) 0.01161(4) Uani 1 1 d . . . . .
I1 I 0.84714(2) 0.32099(3) 0.82097(2) 0.01953(7) Uani 1 1 d . . . . .
I2 I 0.91594(2) 0.66801(3) 0.75804(2) 0.01887(6) Uani 1 1 d . . . . .
I3 I 0.66059(2) 0.63309(3) 0.80108(2) 0.01827(6) Uani 1 1 d . . . . .
I4 I 0.56460(2) 0.33225(3) 0.69004(2) 0.01804(6) Uani 1 1 d . . . . .
I5 I 0.66412(2) 0.66943(2) 0.62269(2) 0.01217(6) Uani 1 1 d . . . . .
I6 I 0.40105(2) 0.67225(3) 0.65581(2) 0.01906(6) Uani 1 1 d . . . . .
I7 I 0.32465(2) 0.31951(2) 0.55275(2) 0.01397(6) Uani 1 1 d . . . . .
I8 I 0.41243(2) 0.66633(2) 0.48414(2) 0.01258(6) Uani 1 1 d . . . . .
I9 I 0.12812(2) 0.62811(3) 0.51870(2) 0.02074(7) Uani 1 1 d . . . . .
I10 I 0.08335(2) 0.29837(3) 0.41555(2) 0.01716(6) Uani 1 1 d . . . . .
I11 I 0.14927(2) 0.66342(2) 0.35324(2) 0.01463(6) Uani 1 1 d . . . . .
S1 S 0.59652(9) 0.99012(11) 0.66021(5) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.8266(3) 1.0250(4) 0.49518(18) 0.0245(9) Uani 1 1 d . . . . .
HN1 H 0.889(5) 1.033(6) 0.500(3) 0.08(2) Uiso 1 1 d . . . . .
N2 N 0.7538(3) 1.0012(3) 0.64189(15) 0.0180(8) Uani 1 1 d . . . . .
N3 N 0.5936(2) 1.0035(3) 0.59593(15) 0.0155(8) Uani 1 1 d . . . . .
N4 N 0.9230(3) 1.0011(3) 0.80354(15) 0.0184(8) Uani 1 1 d . . . . .
HN4 H 0.982832 1.016671 0.809490 0.022 Uiso 1 1 calc R U . . .
C1 C 0.6837(3) 1.0054(4) 0.59313(19) 0.0179(9) Uani 1 1 d . . . . .
C2 C 0.7083(3) 1.0145(4) 0.5404(2) 0.0196(10) Uani 1 1 d . . . . .
C3 C 0.8021(3) 1.0153(4) 0.5424(2) 0.0217(10) Uani 1 1 d . . . . .
H3 H 0.848684 1.009114 0.577046 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7635(4) 1.0353(4) 0.4450(2) 0.0256(11) Uani 1 1 d . . . . .
H1 H 0.783073 1.043723 0.412321 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6704(4) 1.0334(4) 0.44186(19) 0.0234(11) Uani 1 1 d . . . . .
H5 H 0.625256 1.039938 0.406649 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6418(3) 1.0223(4) 0.4888(2) 0.0208(10) Uani 1 1 d . . . . .
H6 H 0.577214 1.019940 0.486320 0.025 Uiso 1 1 calc R U . . .
C7 C 0.7155(3) 0.9923(4) 0.68276(18) 0.0159(9) Uani 1 1 d . . . . .
C8 C 0.7728(3) 0.9851(4) 0.74119(19) 0.0165(9) Uani 1 1 d . . . . .
C9 C 0.8672(3) 1.0081(4) 0.75156(19) 0.0188(10) Uani 1 1 d . . . . .
H9 H 0.892323 1.028851 0.721878 0.023 Uiso 1 1 calc R U . . .
C10 C 0.8919(3) 0.9714(4) 0.8469(2) 0.0201(10) Uani 1 1 d . . . . .
H10 H 0.933950 0.967014 0.883243 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7993(3) 0.9476(4) 0.8386(2) 0.0217(10) Uani 1 1 d . . . . .
H11 H 0.776006 0.926235 0.868949 0.026 Uiso 1 1 calc R U . . .
C12 C 0.7400(3) 0.9550(4) 0.78537(19) 0.0177(9) Uani 1 1 d . . . . .
H12 H 0.675341 0.938973 0.779218 0.021 Uiso 1 1 calc R U . . .
O1 O 1.0281(3) 1.0229(4) 0.56141(15) 0.0333(9) Uani 1 1 d . . . . .
H1O1 H 1.056(5) 0.973(7) 0.591(3) 0.09(3) Uiso 1 1 d . . . . .
C13 C 1.0588(4) 1.1481(5) 0.5788(2) 0.0355(13) Uani 1 1 d . . . . .
H13A H 1.062073 1.197195 0.546473 0.053 Uiso 1 1 calc R U . . .
H13B H 1.120657 1.144821 0.605865 0.053 Uiso 1 1 calc R U . . .
H13C H 1.014533 1.187189 0.596005 0.053 Uiso 1 1 calc R U . . .


_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 2.9065(3) . ?
Bi1 I2 2.9156(4) . ?
Bi1 I3 2.8689(3) . ?
Bi1 I4 3.2952(4) . ?
Bi1 I5 3.3128(4) . ?
Bi1 I11 3.4131(3) 3_666 ?
Bi2 I4 2.9861(3) . ?
Bi2 I5 3.0669(3) . ?
Bi2 I6 2.8628(3) . ?
Bi2 I7 3.1069(3) . ?
Bi2 I8 3.3706(3) 3_666 ?
Bi2 I8 3.1900(4) . ?
Bi3 I5 3.3462(3) 3_666 ?
Bi3 I7 3.1428(3) . ?
Bi3 I8 3.2819(4) . ?
Bi3 I9 2.8677(4) . ?
Bi3 I10 2.9138(3) . ?
Bi3 I11 3.0355(3) . ?
S1 N3 1.607(4) . ?
S1 C7 1.707(5) . ?
N1 HN1 0.91(7) . ?
N1 C3 1.339(6) . ?
N1 C4 1.347(6) . ?
N2 C1 1.368(6) . ?
N2 C7 1.312(6) . ?
N3 C1 1.368(6) . ?
N4 HN4 0.8800 . ?
N4 C9 1.336(6) . ?
N4 C10 1.337(6) . ?
C1 C2 1.473(6) . ?
C2 C3 1.390(7) . ?
C2 C6 1.392(6) . ?
C3 H3 0.9500 . ?
C4 H1 0.9500 . ?
C4 C5 1.371(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.475(6) . ?
C8 C9 1.383(6) . ?
C8 C12 1.371(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.365(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9500 . ?
O1 H1O1 0.90(8) . ?
O1 C13 1.443(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Bi1 I2 94.450(11) . . ?
I1 Bi1 I4 94.401(10) . . ?
I1 Bi1 I5 170.490(9) . . ?
I1 Bi1 I11 87.590(10) . 3_666 ?
I2 Bi1 I4 170.814(10) . . ?
I2 Bi1 I5 86.963(9) . . ?
I2 Bi1 I11 88.937(10) . 3_666 ?
I3 Bi1 I1 95.899(11) . . ?
I3 Bi1 I2 95.081(11) . . ?
I3 Bi1 I4 86.446(10) . . ?
I3 Bi1 I5 93.338(10) . . ?
I3 Bi1 I11 174.448(9) . 3_666 ?
I4 Bi1 I5 83.903(9) . . ?
I4 Bi1 I11 88.986(9) . 3_666 ?
I5 Bi1 I11 83.030(9) . 3_666 ?
I4 Bi2 I5 93.731(10) . . ?
I4 Bi2 I7 87.438(9) . . ?
I4 Bi2 I8 89.377(10) . 3_666 ?
I4 Bi2 I8 172.315(9) . . ?
I5 Bi2 I7 169.665(9) . . ?
I5 Bi2 I8 86.943(9) . 3_666 ?
I5 Bi2 I8 87.774(9) . . ?
I6 Bi2 I4 95.542(11) . . ?
I6 Bi2 I5 91.332(10) . . ?
I6 Bi2 I7 98.782(10) . . ?
I6 Bi2 I8 91.954(10) . . ?
I6 Bi2 I8 174.886(9) . 3_666 ?
I7 Bi2 I8 82.800(9) . 3_666 ?
I7 Bi2 I8 89.749(9) . . ?
I8 Bi2 I8 83.174(9) . 3_666 ?
I7 Bi3 I5 86.606(9) . 3_666 ?
I7 Bi3 I8 87.484(9) . . ?
I8 Bi3 I5 83.980(9) . 3_666 ?
I9 Bi3 I5 178.913(9) . 3_666 ?
I9 Bi3 I7 92.367(10) . . ?
I9 Bi3 I8 96.335(10) . . ?
I9 Bi3 I10 96.530(11) . . ?
I9 Bi3 I11 92.552(10) . . ?
I10 Bi3 I5 83.093(9) . 3_666 ?
I10 Bi3 I7 88.443(9) . . ?
I10 Bi3 I8 166.652(9) . . ?
I10 Bi3 I11 95.988(10) . . ?
I11 Bi3 I5 88.502(10) . 3_666 ?
I11 Bi3 I7 172.966(9) . . ?
I11 Bi3 I8 86.978(9) . . ?
Bi2 I4 Bi1 91.952(9) . . ?
Bi1 I5 Bi3 92.208(9) . 3_666 ?
Bi2 I5 Bi1 90.184(9) . . ?
Bi2 I5 Bi3 96.766(9) . 3_666 ?
Bi2 I7 Bi3 92.621(9) . . ?
Bi2 I8 Bi2 96.826(9) . 3_666 ?
Bi2 I8 Bi3 88.567(8) . . ?
Bi3 I8 Bi2 92.304(9) . 3_666 ?
Bi3 I11 Bi1 95.992(10) . 3_666 ?
N3 S1 C7 93.5(2) . . ?
C3 N1 HN1 114(5) . . ?
C3 N1 C4 122.5(5) . . ?
C4 N1 HN1 123(5) . . ?
C7 N2 C1 107.9(4) . . ?
C1 N3 S1 107.8(3) . . ?
C9 N4 HN4 118.5 . . ?
C9 N4 C10 122.9(4) . . ?
C10 N4 HN4 118.5 . . ?
N2 C1 N3 118.0(4) . . ?
N2 C1 C2 118.8(4) . . ?
N3 C1 C2 123.2(4) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 C6 118.7(5) . . ?
C6 C2 C1 122.9(4) . . ?
N1 C3 C2 119.7(5) . . ?
N1 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
N1 C4 H1 120.5 . . ?
N1 C4 C5 118.9(5) . . ?
C5 C4 H1 120.5 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(5) . . ?
C6 C5 H5 119.6 . . ?
C2 C6 H6 120.3 . . ?
C5 C6 C2 119.4(5) . . ?
C5 C6 H6 120.3 . . ?
N2 C7 S1 112.8(3) . . ?
N2 C7 C8 121.4(4) . . ?
C8 C7 S1 125.8(4) . . ?
C9 C8 C7 116.8(4) . . ?
C12 C8 C7 125.1(4) . . ?
C12 C8 C9 118.0(4) . . ?
N4 C9 C8 119.7(4) . . ?
N4 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N4 C10 H10 120.3 . . ?
N4 C10 C11 119.5(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.9(4) . . ?
C12 C11 H11 120.6 . . ?
C8 C12 C11 121.1(4) . . ?
C8 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C13 O1 H1O1 105(5) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N3 C1 N2 -2.5(4) . . . . ?
S1 N3 C1 C2 178.8(3) . . . . ?
S1 C7 C8 C9 -170.0(3) . . . . ?
S1 C7 C8 C12 11.4(6) . . . . ?
N1 C4 C5 C6 0.5(7) . . . . ?
N2 C1 C2 C3 1.5(6) . . . . ?
N2 C1 C2 C6 -178.4(4) . . . . ?
N2 C7 C8 C9 10.0(6) . . . . ?
N2 C7 C8 C12 -168.5(4) . . . . ?
N3 S1 C7 N2 -1.0(3) . . . . ?
N3 S1 C7 C8 179.1(4) . . . . ?
N3 C1 C2 C3 -179.9(4) . . . . ?
N3 C1 C2 C6 0.2(6) . . . . ?
N4 C10 C11 C12 -0.1(7) . . . . ?
C1 N2 C7 S1 -0.3(4) . . . . ?
C1 N2 C7 C8 179.7(4) . . . . ?
C1 C2 C3 N1 -179.2(4) . . . . ?
C1 C2 C6 C5 178.5(4) . . . . ?
C3 N1 C4 C5 -1.3(7) . . . . ?
C3 C2 C6 C5 -1.5(6) . . . . ?
C4 N1 C3 C2 0.7(7) . . . . ?
C4 C5 C6 C2 0.8(7) . . . . ?
C6 C2 C3 N1 0.7(6) . . . . ?
C7 S1 N3 C1 1.9(3) . . . . ?
C7 N2 C1 N3 1.8(5) . . . . ?
C7 N2 C1 C2 -179.5(4) . . . . ?
C7 C8 C9 N4 -178.9(4) . . . . ?
C7 C8 C12 C11 178.4(4) . . . . ?
C9 N4 C10 C11 -0.3(7) . . . . ?
C9 C8 C12 C11 -0.1(6) . . . . ?
C10 N4 C9 C8 0.5(6) . . . . ?
C10 C11 C12 C8 0.3(7) . . . . ?
C12 C8 C9 N4 -0.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
