# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 2238872'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_global              
;
PROBLEM: Hirshfeld Test Diff for    I1       --Te1      .       22.5 s.u.
RESPONSE: This test is meant for strongly covalently bonded atoms. In cases where bonds are weaker, or where atoms undergo close halogen-halogen bonding, ADPs along the bond direction may not be equal. 
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'Te I6, 2(C5 H6 N), I2'
_chemical_formula_sum            'C10 H12 I8 N2 Te'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            black
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         1303.02

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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   18.0503(11)
_cell_length_b                   10.1185(6)
_cell_length_c                   14.6269(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.830(2)
_cell_angle_gamma                90
_cell_volume                     2557.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      20.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.385
_exptl_crystal_F_000             2248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.105
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    10.819
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6145
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            32971
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.333
_diffrn_reflns_theta_max         30.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3927
_reflns_number_gt                3226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+33.0212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3927
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4104(3) 0.8019(5) 0.3960(4) 0.0328(11) Uani 1 1 d . . . . .
H1N1 H 0.437191 0.874893 0.414183 0.039 Uiso 1 1 calc R U . . .
C1 C 0.4474(3) 0.6891(6) 0.3846(4) 0.0278(11) Uani 1 1 d . . . . .
H1 H 0.501962 0.689126 0.396012 0.033 Uiso 1 1 calc R U . . .
C2 C 0.4066(3) 0.5767(5) 0.3569(3) 0.0222(10) Uani 1 1 d . . . . .
H2 H 0.432617 0.497672 0.349455 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3282(3) 0.5763(6) 0.3398(4) 0.0319(13) Uani 1 1 d . . . . .
H3 H 0.299684 0.497201 0.320155 0.038 Uiso 1 1 calc R U . . .
I4 I 0.70541(2) 0.64451(4) 0.45453(2) 0.02464(8) Uani 1 1 d . . . . .
C4 C 0.2906(3) 0.6908(7) 0.3510(4) 0.0338(13) Uani 1 1 d . . . . .
H4 H 0.236004 0.691545 0.339010 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3325(3) 0.8030(6) 0.3794(4) 0.0305(12) Uani 1 1 d . . . . .
H5 H 0.307124 0.882403 0.387769 0.037 Uiso 1 1 calc R U . . .
I1 I 0.40160(2) -0.02415(4) 0.13916(2) 0.03085(9) Uani 1 1 d . . . . .
Te1 Te 0.500000 0.17136(4) 0.250000 0.01450(9) Uani 1 2 d S T P . .
I2 I 0.40442(2) 0.18060(4) 0.38035(2) 0.03060(9) Uani 1 1 d . . . . .
I3 I 0.59904(2) 0.38773(4) 0.37077(2) 0.03287(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.356(7) . ?
N1 C1 1.356(7) . ?
N1 H1N1 0.8800 . ?
C1 C2 1.352(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.363(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(9) . ?
C3 H3 0.9500 . ?
I4 I4 2.7709(7) 7_666 ?
C4 C5 1.361(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
I1 Te1 2.8336(5) . ?
Te1 I2 2.9198(3) 2_655 ?
Te1 I2 2.9198(3) . ?
Te1 I3 3.0464(5) . ?
Te1 I3 3.0465(5) 2_655 ?

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
C5 N1 C1 120.4(5) . . ?
C5 N1 H1N1 119.8 . . ?
C1 N1 H1N1 119.8 . . ?
C2 C1 N1 120.0(5) . . ?
C2 C1 H1 120.0 . . ?
N1 C1 H1 120.0 . . ?
C1 C2 C3 120.3(5) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 120.2(5) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
I1 Te1 I1 91.44(2) . 2_655 ?
I1 Te1 I2 92.278(13) . 2_655 ?
I1 Te1 I2 90.283(12) 2_655 2_655 ?
I1 Te1 I2 90.285(12) . . ?
I1 Te1 I2 92.278(13) 2_655 . ?
I2 Te1 I2 176.33(2) 2_655 . ?
I1 Te1 I3 177.276(13) . . ?
I1 Te1 I3 90.263(12) 2_655 . ?
I2 Te1 I3 89.838(13) 2_655 . ?
I2 Te1 I3 87.524(12) . . ?
I1 Te1 I3 90.264(12) . 2_655 ?
I1 Te1 I3 177.275(13) 2_655 2_655 ?
I2 Te1 I3 87.524(12) 2_655 2_655 ?
I2 Te1 I3 89.839(13) . 2_655 ?
I3 Te1 I3 88.11(2) . 2_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.3(8) . . . . ?
N1 C1 C2 C3 0.5(8) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C2 C3 C4 C5 -0.2(9) . . . . ?
C1 N1 C5 C4 -0.2(8) . . . . ?
C3 C4 C5 N1 0.4(9) . . . . ?

_refine_diff_density_max         1.681
_refine_diff_density_min         -3.478
_refine_diff_density_rms         0.228

####################################################################### 
# 
# 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_global_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2238875'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_global              
;
PROBLEM: Hirshfeld Test Diff for    I1       --I10_e    .       52.6 s.u.
RESPONSE: This test is meant for strongly covalently bonded atoms. In cases where bonds are weaker, or where atoms undergo close halogen-halogen bonding, ADPs along the bond direction may not be equal. 
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'I6 Te1, 2(C4 H5 N2), 2(I2)'
_chemical_formula_sum            'C8 H8 I10 N4 Te1'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            'metallic gray'
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         1556.82

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'
Cl Cl 0.1484 0.1585 '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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   9.4074(3)
_cell_length_b                   11.5528(4)
_cell_length_c                   13.8021(4)
_cell_angle_alpha                81.7110(10)
_cell_angle_beta                 79.8470(10)
_cell_angle_gamma                69.0100(10)
_cell_volume                     1373.20(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9676
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.770
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    12.327
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.5735
_exptl_absorpt_correction_T_max  0.7561
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            63646
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.895
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8378
_reflns_number_gt                8015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Each pyrazine is singly protonated. Due to symmetry consraints,
the model shows alternating doubly protonated and non
protonated pyrazine molecules.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0056P)²+3.5124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8378
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0405
_refine_ls_wR_factor_gt          0.0401
_refine_ls_goodness_of_fit_ref   1.327
_refine_ls_restrained_S_all      1.327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Te1 Te 1.11038(2) 0.12452(2) 0.21945(2) 0.00758(4) Uani 1 1 d . . . . .
I1 I 1.03171(3) 0.28148(2) 0.38843(2) 0.01526(4) Uani 1 1 d . . . . .
C1 C 0.1507(4) 0.1844(3) 0.7887(3) 0.0149(6) Uani 1 1 d . . . . .
H1 H 0.230506 0.113133 0.811026 0.018 Uiso 1 1 calc R U . . .
N1 N 0.1623(3) 0.2301(3) 0.6945(2) 0.0151(5) Uani 1 1 d . . . . .
HN1 H 0.242627 0.193021 0.652611 0.018 Uiso 1 1 calc R U . . .
N2 N -0.0887(3) 0.3425(3) 0.8226(2) 0.0123(5) Uani 1 1 d . . . . .
I2 I 0.77221(2) 0.15743(2) 0.21264(2) 0.01303(4) Uani 1 1 d . . . . .
C2 C 0.0223(4) 0.2407(3) 0.8540(2) 0.0132(6) Uani 1 1 d . . . . .
H2 H 0.013084 0.207315 0.920924 0.016 Uiso 1 1 calc R U . . .
C3 C -0.0744(4) 0.3898(3) 0.7291(2) 0.0135(6) Uani 1 1 d . . . . .
H3 H -0.151537 0.463569 0.707395 0.016 Uiso 1 1 calc R U . . .
N3 N -0.3654(3) 0.4517(3) 0.9408(2) 0.0136(5) Uani 1 1 d . . . . .
HN3 H -0.292(7) 0.418(5) 0.898(4) 0.047(16) Uiso 1 1 d . . . . .
I3 I 1.19938(2) -0.02040(2) 0.05086(2) 0.01274(4) Uani 1 1 d . . . . .
C4 C 0.0521(4) 0.3321(3) 0.6636(2) 0.0158(6) Uani 1 1 d . . . . .
H4 H 0.060718 0.365044 0.596539 0.019 Uiso 1 1 calc R U . . .
N4 N 0.3924(3) 0.0830(3) 0.5600(2) 0.0144(5) Uani 1 1 d . . . . .
I4 I 1.42387(2) 0.09720(2) 0.21422(2) 0.01244(4) Uani 1 1 d . . . . .
C5 C -0.4239(4) 0.3764(3) 1.0045(3) 0.0159(6) Uani 1 1 d . . . . .
H5 H -0.371415 0.289063 1.008387 0.019 Uiso 1 1 calc R U . . .
I5 I 1.11726(2) -0.09189(2) 0.36169(2) 0.01128(4) Uani 1 1 d . . . . .
I6 I 1.07066(2) 0.35321(2) 0.08355(2) 0.01226(4) Uani 1 1 d . . . . .
C6 C -0.4391(4) 0.5742(3) 0.9352(2) 0.0160(6) Uani 1 1 d . . . . .
H6 H -0.397604 0.627644 0.889699 0.019 Uiso 1 1 calc R U . . .
I8 I 0.45898(2) 0.70762(2) 0.25527(2) 0.01377(4) Uani 1 1 d . . . . .
C8 C 0.5356(4) 0.0845(3) 0.5402(2) 0.0157(6) Uani 1 1 d . . . . .
H8 H 0.562677 0.143149 0.567820 0.019 Uiso 1 1 calc R U . . .
I7 I 0.73408(2) 0.54141(2) 0.18174(2) 0.01179(4) Uani 1 1 d . . . . .
C7 C 0.3543(4) -0.0002(3) 0.5211(2) 0.0158(6) Uani 1 1 d . . . . .
H7 H 0.252355 -0.001539 0.535277 0.019 Uiso 1 1 calc R U . . .
I10 I 0.28229(3) 0.49942(2) 0.49253(2) 0.01685(4) Uani 1 1 d . . . . .
I9 I 0.49866(3) 0.34530(2) 0.36285(2) 0.01605(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Te1 I4 2.8402(3) . ?
Te1 I3 2.8899(3) . ?
Te1 I5 2.9365(3) . ?
Te1 I6 2.9579(3) . ?
Te1 I1 2.9874(3) . ?
Te1 I2 3.0826(3) . ?
C1 N1 1.332(4) . ?
C1 C2 1.385(4) . ?
C1 H1 0.9500 . ?
N1 C4 1.335(4) . ?
N1 HN1 0.8800 . ?
N2 C3 1.330(4) . ?
N2 C2 1.340(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9500 . ?
N3 C6 1.332(4) . ?
N3 C5 1.336(4) . ?
N3 HN3 0.84(6) . ?
C4 H4 0.9500 . ?
N4 C8 1.333(4) . ?
N4 C7 1.343(4) . ?
C5 C6 1.382(5) 2_467 ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
I8 I7 2.7369(3) . ?
C8 C7 1.393(4) 2_656 ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
I10 I9 2.7488(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
I4 Te1 I3 88.567(8) . . ?
I4 Te1 I5 95.875(8) . . ?
I3 Te1 I5 93.301(8) . . ?
I4 Te1 I6 89.179(8) . . ?
I3 Te1 I6 89.410(8) . . ?
I5 Te1 I6 174.318(9) . . ?
I4 Te1 I1 88.834(8) . . ?
I3 Te1 I1 176.659(9) . . ?
I5 Te1 I1 89.052(8) . . ?
I6 Te1 I1 88.455(8) . . ?
I4 Te1 I2 176.835(9) . . ?
I3 Te1 I2 89.184(7) . . ?
I5 Te1 I2 86.477(7) . . ?
I6 Te1 I2 88.572(8) . . ?
I1 Te1 I2 93.330(8) . . ?
N1 C1 C2 120.0(3) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 N1 C4 120.0(3) . . ?
C1 N1 HN1 120.0 . . ?
C4 N1 HN1 120.0 . . ?
C3 N2 C2 119.9(3) . . ?
N2 C2 C1 119.8(3) . . ?
N2 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
N2 C3 C4 120.2(3) . . ?
N2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C6 N3 C5 120.1(3) . . ?
C6 N3 HN3 122(4) . . ?
C5 N3 HN3 117(4) . . ?
N1 C4 C3 120.0(3) . . ?
N1 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C8 N4 C7 119.9(3) . . ?
N3 C5 C6 119.9(3) . 2_467 ?
N3 C5 H5 120.0 . . ?
C6 C5 H5 120.0 2_467 . ?
N3 C6 C5 120.0(3) . 2_467 ?
N3 C6 H6 120.0 . . ?
C5 C6 H6 120.0 2_467 . ?
N4 C8 C7 120.1(3) . 2_656 ?
N4 C8 H8 119.9 . . ?
C7 C8 H8 119.9 2_656 . ?
N4 C7 C8 120.0(3) . 2_656 ?
N4 C7 H7 120.0 . . ?
C8 C7 H7 120.0 2_656 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C4 1.7(5) . . . . ?
C3 N2 C2 C1 -0.8(5) . . . . ?
N1 C1 C2 N2 -1.2(5) . . . . ?
C2 N2 C3 C4 2.1(5) . . . . ?
C1 N1 C4 C3 -0.4(5) . . . . ?
N2 C3 C4 N1 -1.5(5) . . . . ?
C6 N3 C5 C6 -0.2(6) . . . 2_467 ?
C5 N3 C6 C5 0.2(6) . . . 2_467 ?
C7 N4 C8 C7 0.2(6) . . . 2_656 ?
C8 N4 C7 C8 -0.2(5) . . . 2_656 ?

_refine_diff_density_max         1.026
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.169

####################################################################### 
# 
# 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_global_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2238879'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C5 H5 Cl N, I3, H2 O'
_chemical_formula_sum            'C5 H7 Cl I3 N O'
_chemical_melting_point          ?

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         513.27

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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   7.0961(3)
_cell_length_b                   7.8772(3)
_cell_length_c                   11.4958(5)
_cell_angle_alpha                95.461(2)
_cell_angle_beta                 99.379(2)
_cell_angle_gamma                107.782(2)
_cell_volume                     596.48(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7662
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      30.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.858
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    8.041
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.5704
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            21792
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         30.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3661
_reflns_number_gt                2682
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0164P)²+0.4534P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3661
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0582
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.77506(4) 0.25561(3) 0.87938(2) 0.02903(7) Uani 1 1 d . . . . .
O1 O 0.3140(4) 0.3359(3) -0.0287(2) 0.0317(6) Uani 1 1 d G . . . .
HO1 H 0.187217 0.328149 -0.040423 0.048 Uiso 1 1 d G U . . .
H2O1 H 0.312774 0.228652 -0.056149 0.048 Uiso 1 1 d G U . . .
Cl1 Cl 0.7014(2) 0.32985(18) 0.57934(10) 0.0506(3) Uani 1 1 d . . . . .
C1 C 0.4201(6) 0.2595(5) 0.2442(4) 0.0346(9) Uani 1 1 d . . . . .
H1 H 0.311346 0.170830 0.190050 0.042 Uiso 1 1 calc R U . . .
I2 I 0.84155(4) 0.15231(3) 1.11928(2) 0.02299(6) Uani 1 1 d . . . . .
C2 C 0.4742(7) 0.2301(6) 0.3584(4) 0.0391(10) Uani 1 1 d . . . . .
H2 H 0.405002 0.121286 0.384167 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6303(7) 0.3609(6) 0.4345(3) 0.0327(9) Uani 1 1 d . . . . .
I3 I 0.90831(4) 0.04696(3) 1.35287(2) 0.02855(7) Uani 1 1 d . . . . .
C4 C 0.7312(7) 0.5187(5) 0.3973(3) 0.0378(10) Uani 1 1 d . . . . .
H4 H 0.839037 0.609976 0.450361 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6714(7) 0.5405(5) 0.2809(3) 0.0393(11) Uani 1 1 d . . . . .
H5 H 0.739001 0.647297 0.252363 0.047 Uiso 1 1 calc R U . . .
N1 N 0.5190(6) 0.4117(4) 0.2088(3) 0.0308(8) Uani 1 1 d . . . . .
HN1 H 0.479(6) 0.421(5) 0.142(3) 0.026(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.9543(3) . ?
O1 HO1 0.8700 . ?
O1 H2O1 0.8700 . ?
Cl1 C3 1.723(4) . ?
C1 N1 1.330(5) . ?
C1 C2 1.368(6) . ?
C1 H1 0.9500 . ?
I2 I3 2.8938(3) . ?
C2 C3 1.367(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(5) . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.328(5) . ?
C5 H5 0.9500 . ?
N1 HN1 0.79(4) . ?

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
HO1 O1 H2O1 104.5 . . ?
N1 C1 C2 120.3(4) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
I3 I2 I1 179.193(11) . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 Cl1 119.8(3) . . ?
C4 C3 Cl1 119.2(3) . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 119.8(4) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 N1 C1 122.4(4) . . ?
C5 N1 HN1 123(3) . . ?
C1 N1 HN1 115(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 C1 C2 C3 0.5(6) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C1 C2 C3 Cl1 179.4(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
Cl1 C3 C4 C5 -180.0(3) . . . . ?
C3 C4 C5 N1 0.7(6) . . . . ?
C4 C5 N1 C1 -0.3(6) . . . . ?
C2 C1 N1 C5 -0.3(6) . . . . ?

_refine_diff_density_max         1.341
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.167

####################################################################### 
# 
# 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_globalf
_database_code_depnum_ccdc_archive 'CCDC 2238880'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C5 H5 Br N, I3, H2 O'
_chemical_formula_sum            'C5 H7 Br I3 N O'
_chemical_melting_point          ?

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         557.73

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   22.6882(7)
_cell_length_b                   7.0484(2)
_cell_length_c                   15.6003(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.8650(10)
_cell_angle_gamma                90
_cell_volume                     2441.43(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9529
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      30.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.035
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.571
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    10.913
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            31010
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.668
_diffrn_reflns_theta_max         30.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3723
_reflns_number_gt                3034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+6.2644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3723
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0399
_refine_ls_wR_factor_gt          0.0370
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.69162(2) 0.35898(3) 0.37973(2) 0.02326(5) Uani 1 1 d . . . . .
O1 O 0.22462(10) 0.3647(3) 0.41928(14) 0.0267(5) Uani 1 1 d G . . . .
H1O1 H 0.212515 0.334661 0.364389 0.040 Uiso 1 1 d G U . . .
H2O1 H 0.218351 0.486244 0.421069 0.040 Uiso 1 1 d G U . . .
N1 N 0.34967(12) 0.2901(4) 0.45436(17) 0.0243(6) Uani 1 1 d . . . . .
HN1 H 0.313226 0.294675 0.465551 0.029 Uiso 1 1 calc R U . . .
C1 C 0.39536(16) 0.2424(5) 0.5184(2) 0.0323(8) Uani 1 1 d . . . . .
H1 H 0.388442 0.213180 0.574938 0.039 Uiso 1 1 calc R U . . .
I2 I 0.80986(2) 0.33788(3) 0.32680(2) 0.01961(5) Uani 1 1 d . . . . .
C2 C 0.45295(15) 0.2355(5) 0.5026(2) 0.0327(8) Uani 1 1 d . . . . .
H2 H 0.486091 0.201026 0.547764 0.039 Uiso 1 1 calc R U . . .
C3 C 0.46132(14) 0.2796(4) 0.4201(2) 0.0225(6) Uani 1 1 d . . . . .
I3 I 0.92405(2) 0.32824(3) 0.27297(2) 0.02360(5) Uani 1 1 d . . . . .
Br04 Br 0.53946(2) 0.27408(5) 0.39665(3) 0.03697(9) Uani 1 1 d . . . . .
C4 C 0.41315(14) 0.3277(4) 0.3543(2) 0.0248(7) Uani 1 1 d . . . . .
H4 H 0.418867 0.357529 0.297215 0.030 Uiso 1 1 calc R U . . .
C5 C 0.35685(14) 0.3315(4) 0.3733(2) 0.0243(6) Uani 1 1 d . . . . .
H5 H 0.322898 0.363465 0.329051 0.029 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 2.9683(3) . ?
O1 H1O1 0.8700 . ?
O1 H2O1 0.8699 . ?
N1 C1 1.326(4) . ?
N1 C5 1.340(4) . ?
N1 HN1 0.8800 . ?
C1 C2 1.379(4) . ?
C1 H1 0.9500 . ?
I2 I3 2.8839(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 Br04 1.883(3) . ?
C4 C5 1.370(4) . ?
C4 H4 0.9500 . ?
C5 H5 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
H1O1 O1 H2O1 104.5 . . ?
C1 N1 C5 122.5(3) . . ?
C1 N1 HN1 118.7 . . ?
C5 N1 HN1 118.7 . . ?
N1 C1 C2 119.8(3) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
I3 I2 I1 178.303(10) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 Br04 119.6(2) . . ?
C4 C3 Br04 119.6(2) . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 120.0(3) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.4(5) . . . . ?
N1 C1 C2 C3 0.3(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C1 C2 C3 Br04 179.3(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
Br04 C3 C4 C5 -179.7(2) . . . . ?
C1 N1 C5 C4 -0.8(5) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?

_refine_diff_density_max         1.274
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.140

####################################################################### 
# 
# 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_global_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2238881'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_global              
;
PROBLEM: Hirshfeld Test Diff for    I1       --I2       .       20.9 s.u.
RESPONSE: This test is meant for strongly covalently bonded atoms. In cases where bonds are weaker, or where atoms undergo close halogen-halogen bonding, ADPs along the bond direction may not be equal. 
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C5 H5 I N, I3, H2 O'
_chemical_formula_sum            'C5 H7 I4 N O'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         604.72

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   22.8618(8)
_cell_length_b                   7.1336(2)
_cell_length_c                   15.7192(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.2200(10)
_cell_angle_gamma                90
_cell_volume                     2495.66(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9824
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      30.52
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.219
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    9.948
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_T_max  0.7561
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            34068
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.830
_diffrn_reflns_theta_max         30.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3821
_reflns_number_gt                3420
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0073P)²+5.0542P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3821
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0367
_refine_ls_wR_factor_gt          0.0351
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.65248(10) 0.2838(3) 0.54529(14) 0.0221(4) Uani 1 1 d . . . . .
HN1 H 0.688374 0.287370 0.533802 0.026 Uiso 1 1 calc R U . . .
O1 O 0.77663(9) 0.3722(3) 0.57963(12) 0.0243(4) Uani 1 1 d G . . . .
H1O1 H 0.795684 0.334165 0.631100 0.036 Uiso 1 1 d G U . . .
H2O1 H 0.777524 0.494057 0.577704 0.036 Uiso 1 1 d G U . . .
I1 I 0.30432(2) 0.36747(2) 0.62143(2) 0.02175(4) Uani 1 1 d . . . . .
C1 C 0.60587(13) 0.2290(4) 0.48276(16) 0.0284(6) Uani 1 1 d . . . . .
H1 H 0.612023 0.192371 0.427362 0.034 Uiso 1 1 calc R U . . .
C2 C 0.54899(12) 0.2252(4) 0.49771(17) 0.0271(5) Uani 1 1 d . . . . .
H2 H 0.515658 0.186388 0.453224 0.033 Uiso 1 1 calc R U . . .
I2 I 0.18738(2) 0.33918(2) 0.67408(2) 0.01831(4) Uani 1 1 d . . . . .
C3 C 0.54130(11) 0.2793(3) 0.57940(16) 0.0200(4) Uani 1 1 d . . . . .
I3 I 0.07520(2) 0.32632(2) 0.72670(2) 0.02277(4) Uani 1 1 d . . . . .
I4 I 0.45548(2) 0.28250(3) 0.60376(2) 0.02788(4) Uani 1 1 d . . . . .
C4 C 0.59072(12) 0.3322(3) 0.64418(17) 0.0230(5) Uani 1 1 d . . . . .
H4 H 0.586098 0.366774 0.700639 0.028 Uiso 1 1 calc R U . . .
C5 C 0.64655(12) 0.3334(3) 0.62494(17) 0.0227(5) Uani 1 1 d . . . . .
H5 H 0.680889 0.369545 0.668291 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
N1 C1 1.332(3) . ?
N1 C5 1.337(3) . ?
N1 HN1 0.8800 . ?
O1 H1O1 0.8700 . ?
O1 H2O1 0.8700 . ?
I1 I2 2.9808(2) . ?
C1 C2 1.374(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
I2 I3 2.8708(2) . ?
C3 C4 1.389(4) . ?
C3 I4 2.083(2) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 H5 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
C1 N1 C5 122.2(2) . . ?
C1 N1 HN1 118.9 . . ?
C5 N1 HN1 118.9 . . ?
H1O1 O1 H2O1 109.5 . . ?
N1 C1 C2 120.6(2) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
I3 I2 I1 177.868(7) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 I4 120.29(18) . . ?
C2 C3 I4 119.75(19) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 120.1(2) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.3(4) . . . . ?
N1 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C2 C3 I4 178.3(2) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
I4 C3 C4 C5 -178.17(18) . . . . ?
C1 N1 C5 C4 -1.1(4) . . . . ?
C3 C4 C5 N1 -0.2(4) . . . . ?

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_global_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2238876'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'I6 Te, 3(C5 Cl H5 N), I3'
_chemical_formula_sum            'C15 H15 Cl3 I9 N3 Te'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         1613.35

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'
Cl Cl 0.1484 0.1585 '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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   8.9408(3)
_cell_length_b                   9.9568(4)
_cell_length_c                   19.7612(8)
_cell_angle_alpha                103.0060(10)
_cell_angle_beta                 96.6570(10)
_cell_angle_gamma                90.2810(10)
_cell_volume                     1701.62(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9374
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.149
_exptl_crystal_F_000             1412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    9.286
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            28278
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.100
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8455
_reflns_number_gt                6571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0036P)²+5.5649P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8455
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0485
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.61299(4) 0.60253(4) 0.68892(2) 0.01783(9) Uani 1 1 d . . . . .
Cl1 Cl 0.76498(17) 0.41644(17) 0.99523(8) 0.0241(4) Uani 1 1 d . . . . .
Te1 Te 0.40340(4) 0.37768(4) 0.70485(2) 0.01302(8) Uani 1 1 d . . . . .
N1 N 1.1245(5) 0.5150(5) 1.1726(3) 0.0214(12) Uani 1 1 d . . . . .
HN1 H 1.197426 0.535440 1.207571 0.026 Uiso 1 1 calc R U . . .
C1 C 1.0372(6) 0.6148(7) 1.1586(3) 0.0213(14) Uani 1 1 d . . . . .
H1 H 1.052999 0.705796 1.186713 0.026 Uiso 1 1 calc R U . . .
N2 N 0.4170(6) 0.8486(5) 0.8140(3) 0.0261(13) Uani 1 1 d . . . . .
HN2 H 0.420473 0.775155 0.779830 0.031 Uiso 1 1 calc R U . . .
Cl2 Cl 0.3962(2) 1.21451(17) 0.98538(9) 0.0309(4) Uani 1 1 d . . . . .
I2 I 0.14933(4) 0.56855(4) 0.70769(2) 0.02049(10) Uani 1 1 d . . . . .
C2 C 0.9249(7) 0.5877(6) 1.1043(3) 0.0204(14) Uani 1 1 d . . . . .
H2 H 0.862329 0.658800 1.093728 0.024 Uiso 1 1 calc R U . . .
N3 N -0.0956(6) 0.3361(6) 0.5710(3) 0.0246(13) Uani 1 1 d . . . . .
HN3 H -0.026043 0.381710 0.603198 0.029 Uiso 1 1 calc R U . . .
Cl3 Cl -0.43694(18) 0.10231(16) 0.40888(8) 0.0278(4) Uani 1 1 d . . . . .
C3 C 0.9043(7) 0.4543(6) 1.0650(3) 0.0179(13) Uani 1 1 d . . . . .
I3 I 0.33023(4) 0.29025(4) 0.55586(2) 0.01807(9) Uani 1 1 d . . . . .
C4 C 0.9951(7) 0.3498(7) 1.0800(3) 0.0242(15) Uani 1 1 d . . . . .
H4 H 0.981092 0.257914 1.052944 0.029 Uiso 1 1 calc R U . . .
I4 I 0.65790(4) 0.19729(4) 0.70364(2) 0.01713(9) Uani 1 1 d . . . . .
C5 C 1.1065(7) 0.3845(7) 1.1357(3) 0.0234(15) Uani 1 1 d . . . . .
H5 H 1.170619 0.315750 1.148037 0.028 Uiso 1 1 calc R U . . .
I5 I 0.47844(4) 0.48019(4) 0.86002(2) 0.01792(9) Uani 1 1 d . . . . .
I7 I 0.09088(5) 0.17170(4) 0.39136(2) 0.01869(9) Uani 1 1 d . . . . .
C7 C 0.4914(7) 1.0756(7) 0.8662(4) 0.0262(16) Uani 1 1 d . . . . .
H7 H 0.545556 1.157945 0.866207 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4059(7) 1.0710(6) 0.9179(3) 0.0186(14) Uani 1 1 d . . . . .
I8 I 0.08194(4) 0.07998(4) 0.24306(2) 0.01504(8) Uani 1 1 d . . . . .
C6 C 0.4989(7) 0.9595(7) 0.8136(3) 0.0263(15) Uani 1 1 d . . . . .
H6 H 0.561385 0.959008 0.777805 0.032 Uiso 1 1 calc R U . . .
I6 I 0.20619(4) 0.16396(4) 0.72368(2) 0.01850(9) Uani 1 1 d . . . . .
C9 C 0.3210(7) 0.9533(7) 0.9170(4) 0.0274(16) Uani 1 1 d . . . . .
H9 H 0.259246 0.950911 0.952735 0.033 Uiso 1 1 calc R U . . .
I9 I 0.08790(5) -0.03079(4) 0.09066(2) 0.02661(11) Uani 1 1 d . . . . .
C10 C 0.3286(7) 0.8426(7) 0.8641(4) 0.0301(17) Uani 1 1 d . . . . .
H10 H 0.271900 0.760575 0.862046 0.036 Uiso 1 1 calc R U . . .
C11 C -0.1849(7) 0.4081(7) 0.5339(3) 0.0251(15) Uani 1 1 d . . . . .
H11 H -0.175715 0.505760 0.543082 0.030 Uiso 1 1 calc R U . . .
C12 C -0.2898(7) 0.3360(7) 0.4824(3) 0.0239(15) Uani 1 1 d . . . . .
H12 H -0.353014 0.383637 0.454268 0.029 Uiso 1 1 calc R U . . .
C13 C -0.3040(6) 0.1939(6) 0.4713(3) 0.0154(13) Uani 1 1 d . . . . .
C14 C -0.2122(7) 0.1245(6) 0.5121(3) 0.0211(14) Uani 1 1 d . . . . .
H14 H -0.222324 0.027363 0.505842 0.025 Uiso 1 1 calc R U . . .
C15 C -0.1058(7) 0.2003(7) 0.5620(3) 0.0267(16) Uani 1 1 d . . . . .
H15 H -0.039392 0.155269 0.590227 0.032 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 Te1 3.0060(6) . ?
Cl1 C3 1.720(6) . ?
Te1 I6 2.8718(6) . ?
Te1 I3 2.8720(6) . ?
Te1 I4 2.9048(5) . ?
Te1 I2 2.9663(6) . ?
Te1 I5 3.0005(5) . ?
N1 C1 1.324(7) . ?
N1 C5 1.338(8) . ?
N1 HN1 0.8800 . ?
C1 C2 1.360(8) . ?
C1 H1 0.9500 . ?
N2 C6 1.323(8) . ?
N2 C10 1.347(8) . ?
N2 HN2 0.8800 . ?
Cl2 C8 1.731(6) . ?
C2 C3 1.379(8) . ?
C2 H2 0.9500 . ?
N3 C15 1.324(8) . ?
N3 C11 1.339(8) . ?
N3 HN3 0.8800 . ?
Cl3 C13 1.706(6) . ?
C3 C4 1.386(9) . ?
C4 C5 1.376(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
I7 I8 2.8583(6) . ?
C7 C8 1.354(9) . ?
C7 C6 1.378(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(9) . ?
I8 I9 2.9718(6) . ?
C6 H6 0.9500 . ?
C9 C10 1.346(9) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.369(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(8) . ?
C14 C15 1.375(9) . ?
C14 H14 0.9500 . ?
C15 H15 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
I6 Te1 I3 90.105(16) . . ?
I6 Te1 I4 91.064(16) . . ?
I3 Te1 I4 91.862(16) . . ?
I6 Te1 I2 90.322(16) . . ?
I3 Te1 I2 88.913(15) . . ?
I4 Te1 I2 178.411(19) . . ?
I6 Te1 I5 91.444(16) . . ?
I3 Te1 I5 177.81(2) . . ?
I4 Te1 I5 89.652(15) . . ?
I2 Te1 I5 89.536(15) . . ?
I6 Te1 I1 178.567(19) . . ?
I3 Te1 I1 91.297(16) . . ?
I4 Te1 I1 88.589(16) . . ?
I2 Te1 I1 90.006(16) . . ?
I5 Te1 I1 87.164(15) . . ?
C1 N1 C5 122.7(5) . . ?
C1 N1 HN1 118.6 . . ?
C5 N1 HN1 118.6 . . ?
N1 C1 C2 120.3(6) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C6 N2 C10 123.3(6) . . ?
C6 N2 HN2 118.4 . . ?
C10 N2 HN2 118.4 . . ?
C1 C2 C3 118.3(6) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C15 N3 C11 124.0(6) . . ?
C15 N3 HN3 118.0 . . ?
C11 N3 HN3 118.0 . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 Cl1 119.7(5) . . ?
C4 C3 Cl1 119.1(5) . . ?
C5 C4 C3 117.3(6) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
N1 C5 C4 120.0(6) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C8 C7 C6 119.2(6) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.0(6) . . ?
C7 C8 Cl2 120.3(5) . . ?
C9 C8 Cl2 118.7(5) . . ?
I7 I8 I9 175.910(19) . . ?
N2 C6 C7 118.5(6) . . ?
N2 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C10 C9 C8 118.2(6) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 N2 119.7(6) . . ?
C9 C10 H10 120.1 . . ?
N2 C10 H10 120.1 . . ?
N3 C11 C12 117.7(6) . . ?
N3 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C11 C12 C13 120.2(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 Cl3 118.9(5) . . ?
C12 C13 Cl3 121.0(5) . . ?
C15 C14 C13 118.0(6) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
N3 C15 C14 120.1(6) . . ?
N3 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -1.1(9) . . . . ?
N1 C1 C2 C3 0.5(9) . . . . ?
C1 C2 C3 C4 -0.1(10) . . . . ?
C1 C2 C3 Cl1 -179.2(5) . . . . ?
C2 C3 C4 C5 0.1(9) . . . . ?
Cl1 C3 C4 C5 179.2(5) . . . . ?
C1 N1 C5 C4 1.1(10) . . . . ?
C3 C4 C5 N1 -0.6(9) . . . . ?
C6 C7 C8 C9 -2.8(10) . . . . ?
C6 C7 C8 Cl2 179.2(5) . . . . ?
C10 N2 C6 C7 -1.3(10) . . . . ?
C8 C7 C6 N2 2.7(10) . . . . ?
C7 C8 C9 C10 1.5(10) . . . . ?
Cl2 C8 C9 C10 179.6(5) . . . . ?
C8 C9 C10 N2 -0.1(10) . . . . ?
C6 N2 C10 C9 0.0(10) . . . . ?
C15 N3 C11 C12 -2.0(10) . . . . ?
N3 C11 C12 C13 1.8(10) . . . . ?
C11 C12 C13 C14 0.0(10) . . . . ?
C11 C12 C13 Cl3 178.4(5) . . . . ?
C12 C13 C14 C15 -1.6(9) . . . . ?
Cl3 C13 C14 C15 180.0(5) . . . . ?
C11 N3 C15 C14 0.4(10) . . . . ?
C13 C14 C15 N3 1.5(10) . . . . ?

_refine_diff_density_max         1.105
_refine_diff_density_min         -1.066
_refine_diff_density_rms         0.231

####################################################################### 
# 
# 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_global_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2238877'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'I6 Te1, 2(Br1 C5 H5 N1)'
_chemical_formula_sum            'C10 H10 Br2 I6 N2 Te'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         1207.02

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   12.1949(6)
_cell_length_b                   14.1651(7)
_cell_length_c                   14.3164(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.829(2)
_cell_angle_gamma                90
_cell_volume                     2311.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.469
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    12.754
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6157
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            127245
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.891
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5743
_reflns_number_gt                4808
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0081P)²+4.5625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5743
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0362
_refine_ls_wR_factor_gt          0.0331
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Te1 Te 0.49618(2) 0.62345(2) 0.23457(2) 0.00994(5) Uani 1 1 d . . . . .
N1 N 0.9909(3) 0.5565(2) 0.6440(2) 0.0167(7) Uani 1 1 d . . . . .
HN1 H 1.000899 0.618122 0.648326 0.020 Uiso 1 1 calc R U . . .
C1 C 0.8922(3) 0.5206(3) 0.6512(3) 0.0168(8) Uani 1 1 d . . . . .
H1 H 0.835021 0.561048 0.660808 0.020 Uiso 1 1 calc R U . . .
I1 I 0.62029(2) 0.49832(2) 0.15038(2) 0.01675(6) Uani 1 1 d . . . . .
I2 I 0.35799(2) 0.70067(2) 0.04517(2) 0.01459(6) Uani 1 1 d . . . . .
N2 N 0.9741(3) 0.8115(2) 0.0962(2) 0.0168(7) Uani 1 1 d . . . . .
HN2 H 0.982689 0.873133 0.095419 0.020 Uiso 1 1 calc R U . . .
C2 C 0.8752(3) 0.4244(3) 0.6446(3) 0.0145(8) Uani 1 1 d . . . . .
H2 H 0.806181 0.397391 0.649560 0.017 Uiso 1 1 calc R U . . .
I4 I 0.63701(2) 0.54759(2) 0.44194(2) 0.01491(6) Uani 1 1 d . . . . .
Br4 Br 0.92622(4) 0.49114(3) 0.09775(3) 0.01873(9) Uani 1 1 d . . . . .
C4 C 1.0623(3) 0.4067(3) 0.6224(3) 0.0155(8) Uani 1 1 d . . . . .
H4 H 1.120384 0.367901 0.611741 0.019 Uiso 1 1 calc R U . . .
I3 I 0.68388(2) 0.76749(2) 0.26112(2) 0.01449(6) Uani 1 1 d . . . . .
Br3 Br 0.94295(4) 0.23616(3) 0.62593(3) 0.02060(9) Uani 1 1 d . . . . .
C3 C 0.9608(3) 0.3678(3) 0.6304(3) 0.0135(8) Uani 1 1 d . . . . .
C8 C 0.9460(3) 0.6221(3) 0.0970(3) 0.0134(8) Uani 1 1 d . . . . .
C7 C 0.8524(4) 0.6814(3) 0.0908(3) 0.0197(9) Uani 1 1 d . . . . .
H7 H 0.778778 0.656168 0.086885 0.024 Uiso 1 1 calc R U . . .
I6 I 0.37065(2) 0.75928(2) 0.32358(2) 0.01429(6) Uani 1 1 d . . . . .
C6 C 0.8694(4) 0.7770(3) 0.0904(3) 0.0224(9) Uani 1 1 d . . . . .
H6 H 0.806928 0.818928 0.086097 0.027 Uiso 1 1 calc R U . . .
I5 I 0.32186(2) 0.47716(2) 0.21201(2) 0.01393(6) Uani 1 1 d . . . . .
C5 C 1.0753(3) 0.5031(3) 0.6304(3) 0.0187(9) Uani 1 1 d . . . . .
H5 H 1.143720 0.531979 0.626292 0.022 Uiso 1 1 calc R U . . .
C9 C 1.0542(3) 0.6592(3) 0.1041(3) 0.0161(8) Uani 1 1 d . . . . .
H9 H 1.118615 0.619064 0.109542 0.019 Uiso 1 1 calc R U . . .
C10 C 1.0652(3) 0.7574(3) 0.1030(3) 0.0171(8) Uani 1 1 d . . . . .
H10 H 1.137694 0.785190 0.107156 0.020 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
Te1 I2 2.8529(4) . ?
Te1 I1 2.8605(4) . ?
Te1 I5 2.9034(4) . ?
Te1 I3 2.9879(4) . ?
Te1 I6 3.0094(3) . ?
Te1 I4 3.0482(4) . ?
N1 C1 1.344(5) . ?
N1 C5 1.346(5) . ?
N1 HN1 0.8800 . ?
C1 C2 1.376(5) . ?
C1 H1 0.9500 . ?
N2 C10 1.324(5) . ?
N2 C6 1.343(5) . ?
N2 HN2 0.8800 . ?
C2 C3 1.387(5) . ?
C2 H2 0.9500 . ?
Br4 C8 1.872(4) . ?
C4 C5 1.375(5) . ?
C4 C3 1.397(5) . ?
C4 H4 0.9500 . ?
Br3 C3 1.876(4) . ?
C8 C9 1.389(5) . ?
C8 C7 1.394(5) . ?
C7 C6 1.370(6) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C9 C10 1.398(5) . ?
C9 H9 0.9500 . ?
C10 H10 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
I2 Te1 I1 93.401(11) . . ?
I2 Te1 I5 90.353(10) . . ?
I1 Te1 I5 89.255(10) . . ?
I2 Te1 I3 91.492(10) . . ?
I1 Te1 I3 88.886(11) . . ?
I5 Te1 I3 177.456(12) . . ?
I2 Te1 I6 86.550(10) . . ?
I1 Te1 I6 178.403(12) . . ?
I5 Te1 I6 92.341(10) . . ?
I3 Te1 I6 89.519(10) . . ?
I2 Te1 I4 177.020(12) . . ?
I1 Te1 I4 89.579(10) . . ?
I5 Te1 I4 89.622(10) . . ?
I3 Te1 I4 88.626(10) . . ?
I6 Te1 I4 90.473(10) . . ?
C1 N1 C5 123.3(4) . . ?
C1 N1 HN1 118.3 . . ?
C5 N1 HN1 118.3 . . ?
N1 C1 C2 119.2(4) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C10 N2 C6 123.3(4) . . ?
C10 N2 HN2 118.3 . . ?
C6 N2 HN2 118.3 . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C5 C4 C3 117.6(4) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 Br3 119.7(3) . . ?
C4 C3 Br3 119.0(3) . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 Br4 119.7(3) . . ?
C7 C8 Br4 119.6(3) . . ?
C6 C7 C8 118.3(4) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
N2 C6 C7 120.0(4) . . ?
N2 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N1 C5 C4 120.0(4) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C8 C9 C10 117.9(4) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N2 C10 C9 119.7(4) . . ?
N2 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.185

####################################################################### 
# 
# 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_global_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2238873'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_global              
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: The structure has been modeled as a racemic twin using TWIN and BASF commands
;
_vrf_PLAT230_global              
;
PROBLEM: Hirshfeld Test Diff for    I3       --I8_b     .        5.6 s.u.
RESPONSE: This test is meant for strongly covalently bonded atoms. In cases where bonds are weaker, or where atoms undergo close halogen-halogen bonding, ADPs along the bond direction may not be equal. 
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'I6 Te, 2(C5 Cl1 H5 N1), I2'
_chemical_formula_sum            'C10 H10 Cl2 I8 N2 Te'
_chemical_melting_point          440

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         1371.90

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'
Cl Cl 0.1484 0.1585 '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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   19.0162(14)
_cell_length_b                   10.6017(8)
_cell_length_c                   14.2508(11)
_cell_angle_alpha                90
_cell_angle_beta                 111.154(3)
_cell_angle_gamma                90
_cell_volume                     2679.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8343
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.401
_exptl_crystal_F_000             2376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    10.527
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7037
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            32069
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6465
_reflns_number_gt                5773
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.975

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0048P)²+22.7385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(6)
_refine_ls_number_reflns         6465
_refine_ls_number_parameters     209
_refine_ls_number_restraints     152
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7179(8) 0.3346(14) 0.7084(11) 0.028(3) Uani 1 1 d . . . . .
H1 H 0.703288 0.415671 0.723130 0.033 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6251(2) 0.8802(3) 0.4924(3) 0.0295(8) Uani 1 1 d . . . . .
Te1 Te 0.40212(7) 0.18117(6) 0.58279(10) 0.00931(13) Uani 1 1 d . . . . .
I1 I 0.31035(5) 0.19971(9) 0.70806(7) 0.0160(2) Uani 1 1 d . . . . .
N1 N 0.6703(6) 0.2360(12) 0.6938(8) 0.026(3) Uani 1 1 d . . . . .
HN1 H 0.626117 0.248050 0.699023 0.031 Uiso 1 1 calc R U . . .
I2 I 0.30818(5) 0.39425(9) 0.44659(7) 0.0143(2) Uani 1 1 d . . . . .
C2 C 0.7874(8) 0.3172(13) 0.7020(11) 0.024(3) Uani 1 1 d . . . . .
H2 H 0.822133 0.385153 0.714118 0.029 Uiso 1 1 calc R U . . .
N2 N 0.4786(7) 0.5527(10) 0.4674(8) 0.024(3) Uani 1 1 d . . . . .
HN2 H 0.449436 0.486641 0.462351 0.029 Uiso 1 1 calc R U . . .
I3 I 0.51040(5) 0.38333(9) 0.71280(7) 0.0135(2) Uani 1 1 d . . . . .
C3 C 0.8063(7) 0.1978(12) 0.6775(9) 0.016(3) Uani 1 1 d . . . . .
C4 C 0.7546(8) 0.0989(12) 0.6610(10) 0.017(3) Uani 1 1 d . . . . .
H4 H 0.766380 0.017799 0.642494 0.020 Uiso 1 1 calc R U . . .
I4 I 0.49971(5) 0.00132(10) 0.70940(7) 0.0179(2) Uani 1 1 d . . . . .
C5 C 0.6882(8) 0.1193(15) 0.6714(11) 0.021(3) Uani 1 1 d . . . . .
H5 H 0.653713 0.051703 0.662960 0.026 Uiso 1 1 calc R U . . .
I5 I 0.30446(5) -0.00665(10) 0.46435(7) 0.0176(2) Uani 1 1 d . . . . .
I6 I 0.49031(5) 0.18226(9) 0.45013(7) 0.0155(2) Uani 1 1 d . . . . .
C6 C 0.4468(8) 0.6674(14) 0.4536(10) 0.026(3) Uani 1 1 d . . . . .
H6 H 0.394171 0.676839 0.438190 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4916(8) 0.7697(14) 0.4622(10) 0.020(3) Uani 1 1 d . . . . .
H7 H 0.470905 0.852329 0.453220 0.024 Uiso 1 1 calc R U . . .
I7 I 0.20037(5) 0.64441(9) 0.37079(8) 0.0147(2) Uani 1 1 d . . . . .
C8 C 0.5678(7) 0.7515(12) 0.4842(9) 0.016(2) Uani 1 1 d . . . . .
I8 I 0.10972(5) 0.84986(9) 0.28693(8) 0.0147(2) Uani 1 1 d . . . . .
C9 C 0.5980(8) 0.6335(13) 0.4986(11) 0.019(3) Uani 1 1 d . . . . .
H9 H 0.650647 0.621058 0.515481 0.022 Uiso 1 1 calc R U . . .
Cl0A Cl 0.89142(19) 0.1741(3) 0.6681(3) 0.0278(8) Uani 1 1 d . . . . .
C10 C 0.5507(8) 0.5338(13) 0.4880(10) 0.023(3) Uani 1 1 d . . . . .
H10 H 0.569954 0.450261 0.495581 0.028 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
C1 N1 1.348(18) . ?
C1 C2 1.37(2) . ?
C1 H1 0.9500 . ?
Cl1 C8 1.724(13) . ?
Te1 I4 2.8140(14) . ?
Te1 I5 2.8285(14) . ?
Te1 I1 2.9189(16) . ?
Te1 I6 2.9453(16) . ?
Te1 I3 3.0843(13) . ?
Te1 I2 3.0918(14) . ?
N1 C5 1.351(19) . ?
N1 HN1 0.8800 . ?
C2 C3 1.394(18) . ?
C2 H2 0.9500 . ?
N2 C10 1.310(18) . ?
N2 C6 1.340(18) . ?
N2 HN2 0.8800 . ?
C3 C4 1.398(18) . ?
C3 Cl0A 1.690(13) . ?
C4 C5 1.340(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.357(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(19) . ?
C7 H7 0.9500 . ?
I7 I8 2.7671(9) . ?
C8 C9 1.362(19) . ?
C9 C10 1.361(19) . ?
C9 H9 0.9500 . ?
C10 H10 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
N1 C1 C2 119.7(13) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
I4 Te1 I5 92.56(3) . . ?
I4 Te1 I1 93.15(5) . . ?
I5 Te1 I1 90.21(4) . . ?
I4 Te1 I6 91.01(4) . . ?
I5 Te1 I6 91.32(4) . . ?
I1 Te1 I6 175.49(4) . . ?
I4 Te1 I3 86.72(5) . . ?
I5 Te1 I3 179.21(5) . . ?
I1 Te1 I3 90.16(4) . . ?
I6 Te1 I3 88.37(4) . . ?
I4 Te1 I2 174.60(5) . . ?
I5 Te1 I2 91.92(5) . . ?
I1 Te1 I2 89.84(4) . . ?
I6 Te1 I2 85.87(4) . . ?
I3 Te1 I2 88.78(3) . . ?
C1 N1 C5 122.3(12) . . ?
C1 N1 HN1 118.9 . . ?
C5 N1 HN1 118.9 . . ?
C1 C2 C3 118.7(14) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C10 N2 C6 123.5(12) . . ?
C10 N2 HN2 118.3 . . ?
C6 N2 HN2 118.3 . . ?
C2 C3 C4 119.6(13) . . ?
C2 C3 Cl0A 119.7(11) . . ?
C4 C3 Cl0A 120.7(10) . . ?
C5 C4 C3 119.6(13) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 N1 120.1(14) . . ?
C4 C5 H5 120.0 . . ?
N1 C5 H5 120.0 . . ?
N2 C6 C7 118.5(14) . . ?
N2 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C8 118.8(14) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 121.0(12) . . ?
C9 C8 Cl1 119.6(11) . . ?
C7 C8 Cl1 119.4(11) . . ?
C10 C9 C8 118.0(13) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
N2 C10 C9 120.2(14) . . ?
N2 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C5 -1(2) . . . . ?
N1 C1 C2 C3 2(2) . . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C1 C2 C3 Cl0A 179.5(11) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
Cl0A C3 C4 C5 178.3(11) . . . . ?
C3 C4 C5 N1 3(2) . . . . ?
C1 N1 C5 C4 -1(2) . . . . ?
C10 N2 C6 C7 -1(2) . . . . ?
N2 C6 C7 C8 0(2) . . . . ?
C6 C7 C8 C9 -1(2) . . . . ?
C6 C7 C8 Cl1 178.4(11) . . . . ?
C7 C8 C9 C10 2(2) . . . . ?
Cl1 C8 C9 C10 -177.7(11) . . . . ?
C6 N2 C10 C9 1(2) . . . . ?
C8 C9 C10 N2 -2(2) . . . . ?

_refine_diff_density_max         0.976
_refine_diff_density_min         -1.230
_refine_diff_density_rms         0.224

####################################################################### 
# 
# 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_global_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2238878'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'I6 Te1, 2(C5 H5 I1 N1), H2 O1'
_chemical_formula_sum            'C10 H12 I8 N2 O1 Te1'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         1319.05

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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   7.7588(4)
_cell_length_b                   11.8319(4)
_cell_length_c                   14.2751(8)
_cell_angle_alpha                86.842(2)
_cell_angle_beta                 80.992(2)
_cell_angle_gamma                78.3800(10)
_cell_volume                     1267.41(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.88
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.456
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    10.919
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.5643
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            62623
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         27.892
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6045
_reflns_number_gt                5367
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0062P)²+4.8775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6045
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0387
_refine_ls_wR_factor_gt          0.0370
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Te1 Te 1.000000 0.000000 1.000000 0.01296(7) Uani 1 2 d S . P . .
N1 N 0.3980(5) 0.9096(3) 0.6536(2) 0.0208(8) Uani 1 1 d . . . . .
HN1 H 0.428989 0.913119 0.709962 0.025 Uiso 1 1 calc R U . . .
C1 C 0.2944(6) 1.0022(4) 0.6189(3) 0.0243(10) Uani 1 1 d . . . . .
H1 H 0.251459 1.068905 0.656212 0.029 Uiso 1 1 calc R U . . .
O1 O 0.5448(4) 0.8715(3) 0.8180(2) 0.0244(7) Uani 1 1 d G . . . .
H1B H 0.466117 0.877814 0.868990 0.037 Uiso 1 1 d G U . . .
H1C H 0.618671 0.914371 0.827927 0.037 Uiso 1 1 d G U . . .
I1 I 0.67318(4) 0.11969(2) 0.93106(2) 0.01882(6) Uani 1 1 d . . . . .
Te2 Te 1.000000 0.500000 0.500000 0.01219(7) Uani 1 2 d S . P . .
N2 N 0.8267(5) 0.5131(3) 0.8203(3) 0.0242(8) Uani 1 1 d . . . . .
HN2 H 0.855(8) 0.511(5) 0.760(4) 0.053(19) Uiso 1 1 d . . . . .
C2 C 0.2503(6) 1.0005(4) 0.5294(3) 0.0230(9) Uani 1 1 d . . . . .
H2 H 0.179345 1.066335 0.503768 0.028 Uiso 1 1 calc R U . . .
I2 I 1.19833(4) 0.14686(2) 0.87127(2) 0.01763(6) Uani 1 1 d . . . . .
I3 I 0.94771(4) 0.16289(2) 1.15494(2) 0.01813(6) Uani 1 1 d . . . . .
C3 C 0.3115(6) 0.9010(4) 0.4772(3) 0.0199(9) Uani 1 1 d . . . . .
I6 I 0.83506(4) 0.65952(2) 0.36028(2) 0.01740(6) Uani 1 1 d . . . . .
C6 C 0.8434(7) 0.4137(4) 0.8701(3) 0.0270(10) Uani 1 1 d . . . . .
H6 H 0.887173 0.342605 0.838681 0.032 Uiso 1 1 calc R U . . .
I5 I 1.00116(4) 0.30349(2) 0.38132(2) 0.01813(6) Uani 1 1 d . . . . .
C5 C 0.4555(6) 0.8125(4) 0.6053(3) 0.0218(9) Uani 1 1 d . . . . .
H5 H 0.526435 0.748084 0.632665 0.026 Uiso 1 1 calc R U . . .
I4 I 0.65056(3) 0.48022(2) 0.60531(2) 0.01667(6) Uani 1 1 d . . . . .
C4 C 0.4131(6) 0.8046(4) 0.5164(3) 0.0205(9) Uani 1 1 d . . . . .
H4 H 0.452218 0.735058 0.482377 0.025 Uiso 1 1 calc R U . . .
I7 I 0.25680(4) 0.89475(3) 0.33907(2) 0.02884(7) Uani 1 1 d . . . . .
C7 C 0.7970(6) 0.4146(4) 0.9666(3) 0.0235(9) Uani 1 1 d . . . . .
H7 H 0.809618 0.344541 1.002938 0.028 Uiso 1 1 calc R U . . .
I8 I 0.65796(5) 0.52467(3) 1.15730(2) 0.02842(7) Uani 1 1 d . . . . .
C8 C 0.7314(5) 0.5197(4) 1.0106(3) 0.0171(8) Uani 1 1 d . . . . .
C9 C 0.7125(6) 0.6215(4) 0.9567(3) 0.0227(9) Uani 1 1 d . . . . .
H9 H 0.666605 0.693587 0.986149 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7611(6) 0.6163(4) 0.8600(3) 0.0208(9) Uani 1 1 d . . . . .
H10 H 0.748593 0.684878 0.821704 0.025 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
Te1 I1 2.9300(3) 2_757 ?
Te1 I1 2.9300(3) . ?
Te1 I2 2.9333(3) . ?
Te1 I2 2.9333(3) 2_757 ?
Te1 I3 2.9401(3) . ?
Te1 I3 2.9402(3) 2_757 ?
N1 C5 1.335(5) . ?
N1 C1 1.342(6) . ?
N1 HN1 0.8800 . ?
C1 C2 1.376(6) . ?
C1 H1 0.9500 . ?
O1 H1B 0.8700 . ?
O1 H1C 0.8700 . ?
Te2 I6 2.9308(3) . ?
Te2 I6 2.9308(3) 2_766 ?
Te2 I4 2.9336(3) . ?
Te2 I4 2.9337(3) 2_766 ?
Te2 I5 2.9491(3) 2_766 ?
Te2 I5 2.9491(3) . ?
N2 C6 1.334(6) . ?
N2 C10 1.345(6) . ?
N2 HN2 0.85(6) . ?
C2 C3 1.388(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(6) . ?
C3 I7 2.089(4) . ?
C6 C7 1.368(6) . ?
C6 H6 0.9500 . ?
C5 C4 1.371(6) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C7 C8 1.389(6) . ?
C7 H7 0.9500 . ?
I8 C8 2.084(4) . ?
C8 C9 1.388(6) . ?
C9 C10 1.373(6) . ?
C9 H9 0.9500 . ?
C10 H10 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 Te1 I1 180.0 2_757 . ?
I1 Te1 I2 91.158(9) 2_757 . ?
I1 Te1 I2 88.843(8) . . ?
I1 Te1 I2 88.843(8) 2_757 2_757 ?
I1 Te1 I2 91.157(8) . 2_757 ?
I2 Te1 I2 180.0 . 2_757 ?
I1 Te1 I3 88.230(8) 2_757 . ?
I1 Te1 I3 91.771(8) . . ?
I2 Te1 I3 91.448(8) . . ?
I2 Te1 I3 88.553(9) 2_757 . ?
I1 Te1 I3 91.770(8) 2_757 2_757 ?
I1 Te1 I3 88.229(8) . 2_757 ?
I2 Te1 I3 88.552(8) . 2_757 ?
I2 Te1 I3 91.448(8) 2_757 2_757 ?
I3 Te1 I3 180.0 . 2_757 ?
C5 N1 C1 122.0(4) . . ?
C5 N1 HN1 119.0 . . ?
C1 N1 HN1 119.0 . . ?
N1 C1 C2 120.1(4) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
H1B O1 H1C 104.5 . . ?
I6 Te2 I6 180.0 . 2_766 ?
I6 Te2 I4 91.423(8) . . ?
I6 Te2 I4 88.577(8) 2_766 . ?
I6 Te2 I4 88.577(8) . 2_766 ?
I6 Te2 I4 91.423(8) 2_766 2_766 ?
I4 Te2 I4 180.0 . 2_766 ?
I6 Te2 I5 89.985(8) . 2_766 ?
I6 Te2 I5 90.015(8) 2_766 2_766 ?
I4 Te2 I5 88.627(8) . 2_766 ?
I4 Te2 I5 91.373(8) 2_766 2_766 ?
I6 Te2 I5 90.015(8) . . ?
I6 Te2 I5 89.985(8) 2_766 . ?
I4 Te2 I5 91.373(8) . . ?
I4 Te2 I5 88.627(7) 2_766 . ?
I5 Te2 I5 180.0 2_766 . ?
C6 N2 C10 123.2(4) . . ?
C6 N2 HN2 119(4) . . ?
C10 N2 HN2 118(4) . . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 I7 120.8(3) . . ?
C4 C3 I7 119.3(3) . . ?
N2 C6 C7 119.7(4) . . ?
N2 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
N1 C5 C4 120.7(4) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C6 C7 C8 119.0(4) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 I8 119.9(3) . . ?
C7 C8 I8 120.1(3) . . ?
C10 C9 C8 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N2 C10 C9 119.2(4) . . ?
N2 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?

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
C5 N1 C1 C2 -2.7(7) . . . . ?
N1 C1 C2 C3 1.5(7) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C1 C2 C3 I7 -177.9(3) . . . . ?
C10 N2 C6 C7 -1.9(7) . . . . ?
C1 N1 C5 C4 1.4(6) . . . . ?
N1 C5 C4 C3 1.1(6) . . . . ?
C2 C3 C4 C5 -2.3(6) . . . . ?
I7 C3 C4 C5 176.6(3) . . . . ?
N2 C6 C7 C8 0.8(7) . . . . ?
C6 C7 C8 C9 0.4(7) . . . . ?
C6 C7 C8 I8 179.6(3) . . . . ?
C7 C8 C9 C10 -0.6(7) . . . . ?
I8 C8 C9 C10 -179.8(3) . . . . ?
C6 N2 C10 C9 1.7(7) . . . . ?
C8 C9 C10 N2 -0.4(7) . . . . ?

_refine_diff_density_max         1.503
_refine_diff_density_min         -1.744
_refine_diff_density_rms         0.154

####################################################################### 
# 
# 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_global_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2238874'
loop_
_audit_author_name
_audit_author_address
'Christopher Cahill'
;The George Washington University
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_method           'APEX3 v2019.1-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '3(Te1 I6), 6(C5 H5 I1 N1), 3(I2)'
_chemical_formula_sum            'C30 H30 I30 N6 Te3'
_chemical_melting_point          415

_exptl_crystal_description       hexagon
_exptl_crystal_colour            'metallic gray'
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         4664.40

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'
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'
Te Te -0.5308 1.6751 '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'

_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_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.
;

_cell_length_a                   15.0194(10)
_cell_length_b                   15.0194(10)
_cell_length_c                   33.038(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6454.3(10)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9008
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.74
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.600
_exptl_crystal_F_000             5994
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.097
_exptl_absorpt_coefficient_mu    11.800
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5473
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            399168
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.993
_diffrn_reflns_theta_max         26.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             17597
_reflns_number_gt                16119
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;Iodine atoms on 3 iodopyridine molecules were disordered 
which was modeled in two parts, improving the refinement.
These atoms were also constrained with simu and delu 
commands.

ISOR restraints were used on select C and N atoms in the
pyridine rings to prevent NPD status.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0086P)²+20.0148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 7411 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_number_reflns         17597
_refine_ls_number_parameters     652
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0448
_refine_ls_wR_factor_gt          0.0433
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Te1 Te 0.78769(5) 0.57088(4) 0.66205(3) 0.01265(11) Uani 1 1 d . . . . .
I11 I 0.72903(5) 0.69181(6) 0.71303(2) 0.01814(16) Uani 1 1 d . . . . .
I12 I 0.65089(5) 0.37274(5) 0.71019(2) 0.01596(15) Uani 1 1 d . . . . .
I13 I 0.84795(5) 0.44541(5) 0.61258(2) 0.01747(16) Uani 1 1 d . . . . .
I14 I 0.91054(6) 0.74764(6) 0.61364(2) 0.02137(17) Uani 1 1 d . . . . .
I15 I 0.96041(6) 0.62295(6) 0.71291(2) 0.02046(17) Uani 1 1 d . . . . .
I16 I 0.59393(5) 0.51118(6) 0.61183(2) 0.01579(16) Uani 1 1 d . . . . .
Te2 Te 0.45361(5) 0.90085(5) 0.65344(2) 0.01149(17) Uani 1 1 d . . . . .
I21 I 0.47228(6) 1.06385(6) 0.70708(2) 0.01768(16) Uani 1 1 d . . . . .
I22 I 0.27012(5) 0.74861(6) 0.70483(2) 0.01688(16) Uani 1 1 d . . . . .
I23 I 0.42270(6) 0.72034(6) 0.60584(2) 0.01921(17) Uani 1 1 d . . . . .
I24 I 0.62602(6) 1.03888(6) 0.60560(2) 0.01926(17) Uani 1 1 d . . . . .
I25 I 0.60568(6) 0.87803(6) 0.70931(2) 0.01636(16) Uani 1 1 d . . . . .
I26 I 0.31692(6) 0.93132(6) 0.60404(2) 0.01964(17) Uani 1 1 d . . . . .
Te3 Te 0.12229(5) 0.23634(5) 0.66969(2) 0.01166(16) Uani 1 1 d . . . . .
I31 I 0.26554(6) 0.21263(6) 0.71945(2) 0.02056(17) Uani 1 1 d . . . . .
I32 I 0.14520(6) 0.40418(6) 0.71702(2) 0.02070(18) Uani 1 1 d . . . . .
I33 I -0.03211(6) 0.25493(6) 0.61581(2) 0.01704(16) Uani 1 1 d . . . . .
I34 I 0.10731(6) 0.05683(5) 0.61899(2) 0.01606(16) Uani 1 1 d . . . . .
I35 I -0.05626(6) 0.08697(6) 0.71724(2) 0.01859(17) Uani 1 1 d . . . . .
I36 I 0.28458(6) 0.37929(6) 0.61528(2) 0.01740(17) Uani 1 1 d . . . . .
I1A I 0.4133(6) 0.1764(14) 0.47963(11) 0.039(2) Uani 0.49(3) 1 d . U P A 1
I1B I 0.4283(4) 0.2247(13) 0.47919(11) 0.0407(17) Uani 0.51(3) 1 d . U P A 2
N1 N 0.4957(8) 0.2331(7) 0.6215(3) 0.022(2) Uani 1 1 d . . . . .
HN1 H 0.508563 0.236833 0.646960 0.027 Uiso 1 1 calc R U . . .
C1 C 0.5704(9) 0.2482(9) 0.5943(4) 0.026(3) Uani 1 1 d . . . . .
H1A H 0.635280 0.264034 0.603430 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5505(10) 0.2403(10) 0.5546(4) 0.032(3) Uani 1 1 d . . . . .
H2 H 0.601590 0.250950 0.536159 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4547(9) 0.2165(10) 0.5411(4) 0.023(3) Uani 1 1 d . U . . .
C4 C 0.3788(9) 0.2037(9) 0.5688(4) 0.022(3) Uani 1 1 d . . . . .
H4 H 0.314081 0.189444 0.560181 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4030(10) 0.2127(9) 0.6089(4) 0.024(3) Uani 1 1 d . . . . .
H5A H 0.353745 0.204448 0.627904 0.029 Uiso 1 1 calc R U . . .
I2 I 0.78925(7) 0.53427(8) 0.51250(3) 0.0393(2) Uani 1 1 d . . . . .
N2 N 0.7343(8) 0.5649(7) 0.3717(3) 0.021(2) Uani 1 1 d . . . . .
HN2 H 0.724648 0.570992 0.346460 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6561(10) 0.5355(9) 0.3969(4) 0.027(3) Uani 1 1 d . . . . .
H6A H 0.592321 0.521237 0.387032 0.033 Uiso 1 1 calc R U . . .
C7 C 0.6679(9) 0.5260(9) 0.4366(4) 0.027(3) Uani 1 1 d . . . . .
H7 H 0.612652 0.505170 0.454148 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7645(9) 0.5475(8) 0.4515(4) 0.018(3) Uani 1 1 d . . . . .
C9 C 0.8438(9) 0.5784(9) 0.4239(4) 0.020(3) Uani 1 1 d . . . . .
H9 H 0.908815 0.594252 0.432856 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8280(10) 0.5858(9) 0.3839(4) 0.023(3) Uani 1 1 d . . . . .
H10 H 0.881013 0.604899 0.365291 0.028 Uiso 1 1 calc R U . . .
I3 I 0.07687(7) 0.53146(7) 0.47404(3) 0.02721(19) Uani 1 1 d . . . . .
N3 N 0.1371(7) 0.6136(8) 0.6155(3) 0.022(2) Uani 1 1 d . . . . .
HN3 H 0.148093 0.628385 0.640811 0.027 Uiso 1 1 calc R U . . .
C11 C 0.1074(8) 0.6678(9) 0.5917(4) 0.021(3) Uani 1 1 d . . . . .
H11 H 0.099582 0.720354 0.602783 0.025 Uiso 1 1 calc R U . . .
C12 C 0.0889(9) 0.6447(9) 0.5512(4) 0.019(3) Uani 1 1 d . . . . .
H12 H 0.067818 0.680829 0.534689 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1024(8) 0.5669(8) 0.5356(4) 0.015(3) Uani 1 1 d . U . . .
C14 C 0.1328(9) 0.5124(9) 0.5607(4) 0.024(3) Uani 1 1 d . . . . .
H14 H 0.141300 0.459659 0.550227 0.029 Uiso 1 1 calc R U . . .
C15 C 0.1500(9) 0.5369(9) 0.6005(4) 0.025(3) Uani 1 1 d . . . . .
H15 H 0.170485 0.501118 0.617498 0.030 Uiso 1 1 calc R U . . .
I4 I 0.14828(7) 0.25067(7) 0.51767(3) 0.02658(19) Uani 1 1 d . . . . .
N4 N 0.0815(8) 0.1691(7) 0.3768(3) 0.021(2) Uani 1 1 d . U . . .
HN4 H 0.071151 0.155277 0.351365 0.026 Uiso 1 1 calc R U . . .
C16 C 0.1128(9) 0.1177(9) 0.3982(4) 0.026(3) Uani 1 1 d . . . . .
H16 H 0.122182 0.066940 0.386209 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1323(8) 0.1389(9) 0.4395(3) 0.021(3) Uani 1 1 d . . . . .
H17 H 0.155489 0.103224 0.455228 0.025 Uiso 1 1 calc R U . . .
C18 C 0.1165(8) 0.2135(9) 0.4564(4) 0.020(3) Uani 1 1 d . . . . .
C19 C 0.0828(9) 0.2676(9) 0.4320(4) 0.023(3) Uani 1 1 d . . . . .
H19 H 0.073210 0.319221 0.442932 0.028 Uiso 1 1 calc R U . . .
C20 C 0.0642(9) 0.2428(9) 0.3916(4) 0.025(3) Uani 1 1 d . . . . .
H20 H 0.040238 0.276073 0.374933 0.030 Uiso 1 1 calc R U . . .
I5A I 0.42737(11) 0.82037(13) 0.50817(4) 0.0420(5) Uani 0.778(4) 1 d . U P B 1
I5B I 0.4144(6) 0.8948(8) 0.50705(17) 0.095(4) Uani 0.222(4) 1 d . U P B 2
N5 N 0.4666(10) 0.9149(10) 0.3682(5) 0.040(3) Uani 1 1 d . . . . .
HN5 H 0.475569 0.928484 0.342721 0.048 Uiso 1 1 calc R U . . .
C21 C 0.3977(9) 0.8201(9) 0.3792(4) 0.022(3) Uani 1 1 d . . . . .
H21 H 0.360189 0.770052 0.359953 0.027 Uiso 1 1 calc R U . . .
C22 C 0.3831(9) 0.7976(10) 0.4195(4) 0.030(3) Uani 1 1 d . . . . .
H22 H 0.333021 0.732537 0.427967 0.036 Uiso 1 1 calc R U . . .
C23 C 0.4411(10) 0.8694(13) 0.4470(5) 0.037(4) Uani 1 1 d . . . . .
C24 C 0.5098(10) 0.9679(11) 0.4350(5) 0.043(4) Uani 1 1 d . . . . .
H24 H 0.547322 1.018936 0.453940 0.051 Uiso 1 1 calc R U . . .
C25 C 0.5219(10) 0.9892(10) 0.3938(6) 0.041(4) Uani 1 1 d . . . . .
H25 H 0.568275 1.054896 0.384509 0.050 Uiso 1 1 calc R U . . .
I6A I 0.82451(10) 0.87706(13) 0.48314(3) 0.0441(5) Uani 0.881(5) 1 d . U P C 1
I6B I 0.8014(13) 0.9414(13) 0.4823(3) 0.096(7) Uani 0.119(5) 1 d . U P C 2
N6 N 0.7537(8) 0.8811(8) 0.6244(4) 0.024(3) Uani 1 1 d . . . . .
HN6 H 0.742579 0.879121 0.650029 0.029 Uiso 1 1 calc R U . . .
C27 C 0.8517(9) 0.9687(10) 0.5679(4) 0.029(3) Uani 1 1 d . . . . .
H27 H 0.905975 1.027278 0.556472 0.035 Uiso 1 1 calc R U . . .
C28 C 0.7912(10) 0.8810(10) 0.5442(4) 0.028(3) Uani 1 1 d . . . . .
C29 C 0.7097(9) 0.7960(10) 0.5621(4) 0.032(3) Uani 1 1 d . . . . .
H29 H 0.666443 0.738413 0.546766 0.039 Uiso 1 1 calc R U . . .
C30 C 0.6942(9) 0.7980(10) 0.6018(5) 0.033(3) Uani 1 1 d . . . . .
H30 H 0.640797 0.740319 0.614084 0.040 Uiso 1 1 calc R U . . .
C26 C 0.8293(9) 0.9663(9) 0.6082(4) 0.027(3) Uani 1 1 d . . . . .
H26 H 0.866977 1.024346 0.624171 0.032 Uiso 1 1 calc R U . . .
I41 I 0.11469(6) 0.94118(6) 0.53264(2) 0.02050(16) Uani 1 1 d . . . . .
I42 I 0.11797(6) 0.84170(6) 0.46307(2) 0.02204(17) Uani 1 1 d . . . . .
I51 I 0.47705(6) 0.52111(6) 0.52641(2) 0.02006(16) Uani 1 1 d . . . . .
I52 I 0.37433(6) 0.52784(6) 0.45853(2) 0.02161(17) Uani 1 1 d . . . . .
I61 I 0.84605(6) 0.24054(6) 0.52689(2) 0.02400(16) Uani 1 1 d . . . . .
I62 I 0.74303(5) 0.25046(5) 0.45979(2) 0.01992(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Te1 I14 2.8482(11) . ?
Te1 I15 2.8522(11) . ?
Te1 I11 2.9176(11) . ?
Te1 I13 2.9575(11) . ?
Te1 I16 3.0688(11) . ?
Te1 I12 3.0811(10) . ?
Te2 I26 2.8333(10) . ?
Te2 I24 2.8518(10) . ?
Te2 I21 2.9200(10) . ?
Te2 I23 2.9631(10) . ?
Te2 I22 3.0668(10) . ?
Te2 I25 3.0860(10) . ?
Te3 I32 2.8373(10) . ?
Te3 I31 2.8678(11) . ?
Te3 I36 2.9240(11) . ?
Te3 I35 2.9455(11) . ?
Te3 I33 3.0452(10) . ?
Te3 I34 3.0853(10) . ?
I1A C3 2.122(15) . ?
I1B C3 2.100(14) . ?
N1 C5 1.334(16) . ?
N1 C1 1.363(16) . ?
N1 HN1 0.8600 . ?
C1 C2 1.337(18) . ?
C1 H1A 0.9300 . ?
C2 C3 1.372(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(18) . ?
C4 C5 1.361(17) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9300 . ?
I2 C8 2.076(14) . ?
N2 C6 1.322(16) . ?
N2 C10 1.342(16) . ?
N2 HN2 0.8600 . ?
C6 C7 1.339(18) . ?
C6 H6A 0.9300 . ?
C7 C8 1.408(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(17) . ?
C9 C10 1.357(17) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
I3 C13 2.087(13) . ?
N3 C15 1.352(16) . ?
N3 C11 1.357(15) . ?
N3 HN3 0.8600 . ?
C11 C12 1.375(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(16) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(17) . ?
C14 C15 1.356(17) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
I4 C18 2.091(13) . ?
N4 C16 1.296(16) . ?
N4 C20 1.350(15) . ?
N4 HN4 0.8600 . ?
C16 C17 1.398(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(17) . ?
C17 H17 0.9300 . ?
C18 C19 1.406(17) . ?
C19 C20 1.374(17) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
I5A C23 2.125(15) . ?
I5B C23 2.096(17) . ?
N5 C25 1.31(2) . ?
N5 C21 1.326(17) . ?
N5 HN5 0.8600 . ?
C21 C22 1.363(17) . ?
C21 H21 0.9300 . ?
C22 C23 1.34(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.37(2) . ?
C24 C25 1.39(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
I6A C28 2.085(15) . ?
I6B C28 2.210(19) . ?
N6 C26 1.327(16) . ?
N6 C30 1.341(18) . ?
N6 HN6 0.8600 . ?
C27 C26 1.368(18) . ?
C27 C28 1.408(18) . ?
C27 H27 0.9300 . ?
C28 C29 1.385(18) . ?
C29 C30 1.334(19) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C26 H26 0.9300 . ?
I41 I42 2.7553(10) . ?
I51 I52 2.7522(11) . ?
I61 I62 2.7500(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
I14 Te1 I15 89.93(3) . . ?
I14 Te1 I11 90.02(3) . . ?
I15 Te1 I11 90.32(4) . . ?
I14 Te1 I13 91.24(3) . . ?
I15 Te1 I13 88.52(3) . . ?
I11 Te1 I13 178.28(5) . . ?
I14 Te1 I16 92.66(3) . . ?
I15 Te1 I16 176.62(4) . . ?
I11 Te1 I16 87.51(3) . . ?
I13 Te1 I16 93.59(3) . . ?
I14 Te1 I12 176.91(4) . . ?
I15 Te1 I12 92.10(3) . . ?
I11 Te1 I12 92.30(3) . . ?
I13 Te1 I12 86.48(3) . . ?
I16 Te1 I12 85.41(2) . . ?
I26 Te2 I24 91.79(3) . . ?
I26 Te2 I21 89.30(3) . . ?
I24 Te2 I21 93.16(3) . . ?
I26 Te2 I23 92.72(3) . . ?
I24 Te2 I23 92.35(3) . . ?
I21 Te2 I23 174.07(4) . . ?
I26 Te2 I22 89.18(3) . . ?
I24 Te2 I22 178.59(3) . . ?
I21 Te2 I22 87.87(3) . . ?
I23 Te2 I22 86.58(3) . . ?
I26 Te2 I25 177.14(3) . . ?
I24 Te2 I25 87.64(3) . . ?
I21 Te2 I25 87.93(3) . . ?
I23 Te2 I25 90.11(3) . . ?
I22 Te2 I25 91.44(3) . . ?
I32 Te3 I31 91.67(3) . . ?
I32 Te3 I36 90.01(3) . . ?
I31 Te3 I36 92.40(3) . . ?
I32 Te3 I35 92.44(3) . . ?
I31 Te3 I35 93.07(3) . . ?
I36 Te3 I35 173.93(4) . . ?
I32 Te3 I33 90.01(3) . . ?
I31 Te3 I33 178.24(3) . . ?
I36 Te3 I33 88.09(3) . . ?
I35 Te3 I33 86.36(3) . . ?
I32 Te3 I34 177.50(3) . . ?
I31 Te3 I34 86.23(3) . . ?
I36 Te3 I34 88.72(3) . . ?
I35 Te3 I34 89.03(3) . . ?
I33 Te3 I34 92.09(3) . . ?
C5 N1 C1 120.8(11) . . ?
C5 N1 HN1 119.6 . . ?
C1 N1 HN1 119.6 . . ?
C2 C1 N1 120.1(11) . . ?
C2 C1 H1A 120.0 . . ?
N1 C1 H1A 120.0 . . ?
C1 C2 C3 120.1(12) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.0(12) . . ?
C2 C3 I1B 120.4(10) . . ?
C4 C3 I1B 118.8(9) . . ?
C2 C3 I1A 120.4(10) . . ?
C4 C3 I1A 119.0(9) . . ?
C5 C4 C3 117.7(12) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
N1 C5 C4 121.4(12) . . ?
N1 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C6 N2 C10 122.9(11) . . ?
C6 N2 HN2 118.6 . . ?
C10 N2 HN2 118.6 . . ?
N2 C6 C7 120.5(12) . . ?
N2 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C6 C7 C8 119.7(12) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 117.4(12) . . ?
C9 C8 I2 120.4(9) . . ?
C7 C8 I2 122.2(10) . . ?
C10 C9 C8 120.9(11) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
N2 C10 C9 118.6(11) . . ?
N2 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C15 N3 C11 121.9(11) . . ?
C15 N3 HN3 119.1 . . ?
C11 N3 HN3 119.1 . . ?
N3 C11 C12 119.9(11) . . ?
N3 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 118.7(11) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C14 120.2(12) . . ?
C12 C13 I3 119.6(9) . . ?
C14 C13 I3 120.2(9) . . ?
C15 C14 C13 119.5(11) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
N3 C15 C14 119.8(11) . . ?
N3 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C16 N4 C20 124.4(11) . . ?
C16 N4 HN4 117.8 . . ?
C20 N4 HN4 117.8 . . ?
N4 C16 C17 119.6(11) . . ?
N4 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 118.7(11) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 119.8(12) . . ?
C17 C18 I4 120.1(9) . . ?
C19 C18 I4 120.1(9) . . ?
C20 C19 C18 118.8(11) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
N4 C20 C19 118.6(11) . . ?
N4 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C25 N5 C21 123.9(14) . . ?
C25 N5 HN5 118.1 . . ?
C21 N5 HN5 118.1 . . ?
N5 C21 C22 118.5(12) . . ?
N5 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C23 C22 C21 120.1(13) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.3(14) . . ?
C22 C23 I5B 132.8(11) . . ?
C24 C23 I5B 100.8(12) . . ?
C22 C23 I5A 117.0(11) . . ?
C24 C23 I5A 122.6(12) . . ?
C23 C24 C25 118.2(13) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
N5 C25 C24 118.7(13) . . ?
N5 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C26 N6 C30 121.5(13) . . ?
C26 N6 HN6 119.2 . . ?
C30 N6 HN6 119.2 . . ?
C26 C27 C28 118.9(12) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C29 C28 C27 118.9(13) . . ?
C29 C28 I6A 120.1(10) . . ?
C27 C28 I6A 120.9(10) . . ?
C29 C28 I6B 128.5(11) . . ?
C27 C28 I6B 104.6(10) . . ?
C30 C29 C28 118.9(12) . . ?
C30 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
C29 C30 N6 121.8(12) . . ?
C29 C30 H30 119.1 . . ?
N6 C30 H30 119.1 . . ?
N6 C26 C27 119.9(12) . . ?
N6 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?

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
C5 N1 C1 C2 -1.5(18) . . . . ?
N1 C1 C2 C3 -0.3(19) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C1 C2 C3 I1B 171.1(11) . . . . ?
C1 C2 C3 I1A -168.5(11) . . . . ?
C2 C3 C4 C5 -1.9(18) . . . . ?
I1B C3 C4 C5 -171.1(10) . . . . ?
I1A C3 C4 C5 168.8(11) . . . . ?
C1 N1 C5 C4 1.7(18) . . . . ?
C3 C4 C5 N1 0.0(18) . . . . ?
C10 N2 C6 C7 0.6(18) . . . . ?
N2 C6 C7 C8 0.0(18) . . . . ?
C6 C7 C8 C9 0.2(17) . . . . ?
C6 C7 C8 I2 -179.8(9) . . . . ?
C7 C8 C9 C10 -1.0(17) . . . . ?
I2 C8 C9 C10 179.0(9) . . . . ?
C6 N2 C10 C9 -1.4(17) . . . . ?
C8 C9 C10 N2 1.6(17) . . . . ?
C15 N3 C11 C12 0.4(17) . . . . ?
N3 C11 C12 C13 -0.7(17) . . . . ?
C11 C12 C13 C14 0.8(17) . . . . ?
C11 C12 C13 I3 -179.2(8) . . . . ?
C12 C13 C14 C15 -0.6(18) . . . . ?
I3 C13 C14 C15 179.4(9) . . . . ?
C11 N3 C15 C14 -0.1(18) . . . . ?
C13 C14 C15 N3 0.2(18) . . . . ?
C20 N4 C16 C17 -1.1(18) . . . . ?
N4 C16 C17 C18 0.7(17) . . . . ?
C16 C17 C18 C19 -0.9(17) . . . . ?
C16 C17 C18 I4 -178.4(8) . . . . ?
C17 C18 C19 C20 1.3(17) . . . . ?
I4 C18 C19 C20 178.9(9) . . . . ?
C16 N4 C20 C19 1.5(18) . . . . ?
C18 C19 C20 N4 -1.6(17) . . . . ?
C25 N5 C21 C22 -0.2(19) . . . . ?
N5 C21 C22 C23 -2.9(19) . . . . ?
C21 C22 C23 C24 5(2) . . . . ?
C21 C22 C23 I5B 151.8(13) . . . . ?
C21 C22 C23 I5A -171.3(9) . . . . ?
C22 C23 C24 C25 -4(2) . . . . ?
I5B C23 C24 C25 -159.6(12) . . . . ?
I5A C23 C24 C25 172.3(10) . . . . ?
C21 N5 C25 C24 1(2) . . . . ?
C23 C24 C25 N5 1(2) . . . . ?
C26 C27 C28 C29 1.4(19) . . . . ?
C26 C27 C28 I6A -177.6(9) . . . . ?
C26 C27 C28 I6B 152.8(12) . . . . ?
C27 C28 C29 C30 -3(2) . . . . ?
I6A C28 C29 C30 175.6(10) . . . . ?
I6B C28 C29 C30 -147.1(13) . . . . ?
C28 C29 C30 N6 2(2) . . . . ?
C26 N6 C30 C29 1.7(19) . . . . ?
C30 N6 C26 C27 -3.7(18) . . . . ?
C28 C27 C26 N6 2.1(18) . . . . ?

_refine_diff_density_max         1.215
_refine_diff_density_min         -1.165
_refine_diff_density_rms         0.152

