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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umt_ob193
_database_code_depnum_ccdc_archive 'CCDC 2075098'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2020-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 I2 N, I'
_chemical_formula_sum            'C23 H16 I3 N'
_chemical_formula_weight         687.07
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   21.1343(8)
_cell_length_b                   13.7339(7)
_cell_length_c                   7.3280(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2127.00(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.034
_cell_measurement_theta_min      2.966
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.417
_exptl_absorpt_coefficient_mu    4.416
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0783 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.8017. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28749
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.077
_diffrn_reflns_theta_max         25.077
_diffrn_reflns_theta_min         2.966
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1459
_reflns_number_total             1892
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (BRUKER, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0133P)²+0.3762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0345
_refine_ls_wR_factor_ref         0.0382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H12A(0.5) H12B(0.5) H12C(0.5) H13A(0.5) H13B(0.5) H13C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C9(H9), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.64653(2) 0.68482(2) 0.35677(3) 0.01305(7) Uani 1 1 d . . . . .
I2 I 0.500000 0.82133(3) 0.250000 0.01410(9) Uani 1 2 d S T P . .
N1 N 0.500000 0.2072(3) 0.250000 0.0105(11) Uani 1 2 d S T P . .
C1 C 0.55350(18) 0.2559(3) 0.2896(5) 0.0114(9) Uani 1 1 d . . . . .
H1 H 0.590864 0.220390 0.317489 0.014 Uiso 1 1 calc R . . . .
C2 C 0.55516(18) 0.3556(3) 0.2906(5) 0.0104(9) Uani 1 1 d . . . . .
C3 C 0.500000 0.4092(4) 0.250000 0.0116(13) Uani 1 2 d S T P . .
C4 C 0.61368(18) 0.4046(3) 0.3326(5) 0.0114(9) Uani 1 1 d . . . . .
C5 C 0.66069(17) 0.4474(3) 0.3684(6) 0.0118(9) Uani 1 1 d . . . . .
C6 C 0.71876(18) 0.4951(3) 0.4157(5) 0.0132(9) Uani 1 1 d . . . . .
C7 C 0.72469(17) 0.5962(3) 0.4251(5) 0.0123(9) Uani 1 1 d . . . . .
C8 C 0.78134(18) 0.6390(3) 0.4785(5) 0.0144(10) Uani 1 1 d . . . . .
H8 H 0.784982 0.707860 0.484407 0.017 Uiso 1 1 calc R . . . .
C9 C 0.83249(19) 0.5805(3) 0.5231(6) 0.0194(10) Uani 1 1 d . . . . .
H9 H 0.870945 0.609468 0.562455 0.023 Uiso 1 1 calc R . . . .
C10 C 0.82805(18) 0.4805(3) 0.5110(6) 0.0196(11) Uani 1 1 d . . . . .
H10 H 0.863711 0.441083 0.538731 0.024 Uiso 1 1 calc R . . . .
C11 C 0.77197(17) 0.4378(3) 0.4587(5) 0.0150(9) Uani 1 1 d . . . . .
H11 H 0.769131 0.368861 0.451456 0.018 Uiso 1 1 calc R . . . .
C12 C 0.500000 0.0998(4) 0.250000 0.0158(14) Uani 1 2 d S T P . .
H12A H 0.516527 0.075990 0.133271 0.024 Uiso 0.5 1 calc GR . . A -1
H12B H 0.456685 0.075990 0.267086 0.024 Uiso 0.5 1 calc GR . . A -1
H12C H 0.526788 0.075990 0.349643 0.024 Uiso 0.5 1 calc GR . . A -1
C13 C 0.500000 0.5175(4) 0.250000 0.0205(15) Uani 1 2 d S T P . .
H13A H 0.505836 0.541266 0.374957 0.031 Uiso 0.5 1 calc GR . . B -1
H13B H 0.459560 0.541266 0.202099 0.031 Uiso 0.5 1 calc GR . . B -1
H13C H 0.534604 0.541266 0.172944 0.031 Uiso 0.5 1 calc GR . . B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.112(4) . ?
N1 C1 1.345(4) . ?
N1 C1 1.345(4) 3_655 ?
N1 C12 1.475(7) . ?
C1 C2 1.370(5) . ?
C2 C3 1.411(5) . ?
C2 C4 1.441(5) . ?
C3 C13 1.487(8) . ?
C4 C5 1.183(5) . ?
C5 C6 1.434(5) . ?
C6 C7 1.395(6) . ?
C6 C11 1.408(5) . ?
C7 C8 1.390(5) . ?
C8 C9 1.386(5) . ?
C9 C10 1.379(6) . ?
C10 C11 1.377(5) . ?

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 C1 120.4(5) 3_655 . ?
C1 N1 C12 119.8(2) . . ?
C1 N1 C12 119.8(2) 3_655 . ?
N1 C1 C2 121.3(4) . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 C4 119.4(4) . . ?
C3 C2 C4 120.7(4) . . ?
C2 C3 C2 117.0(5) 3_655 . ?
C2 C3 C13 121.5(3) 3_655 . ?
C2 C3 C13 121.5(3) . . ?
C5 C4 C2 178.0(4) . . ?
C4 C5 C6 177.3(4) . . ?
C7 C6 C5 122.9(4) . . ?
C7 C6 C11 118.3(4) . . ?
C11 C6 C5 118.8(4) . . ?
C6 C7 I1 119.4(3) . . ?
C8 C7 I1 119.8(3) . . ?
C8 C7 C6 120.8(4) . . ?
C9 C8 C7 119.5(4) . . ?
C10 C9 C8 120.6(4) . . ?
C11 C10 C9 120.0(4) . . ?
C10 C11 C6 120.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umt_ob154
_database_code_depnum_ccdc_archive 'CCDC 2075101'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2020-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 I2 N, I'
_chemical_formula_sum            'C22 H14 I3 N'
_chemical_formula_weight         673.04
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0838(2)
_cell_length_b                   11.8898(4)
_cell_length_c                   12.2871(4)
_cell_angle_alpha                64.3550(10)
_cell_angle_beta                 77.9010(10)
_cell_angle_gamma                77.3900(10)
_cell_volume                     1030.02(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.345
_cell_measurement_theta_min      2.604
_shelx_estimated_absorpt_T_max   0.712
_shelx_estimated_absorpt_T_min   0.478
_exptl_absorpt_coefficient_mu    4.557
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0539 before and 0.0402 after correction. The Ratio of minimum to maximum transmission is 0.8754. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prisim
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            43567
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.358
_diffrn_reflns_theta_min         2.604
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4674
_reflns_number_total             5147
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (BRUKER, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0171
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0155P)²+0.7643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0352
_refine_ls_wR_factor_ref         0.0362
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.20643(2) 0.28699(2) 0.75498(2) 0.01799(4) Uani 1 1 d . . . . .
I2 I 0.37436(2) 0.81880(2) 0.47152(2) 0.01807(4) Uani 1 1 d . . . . .
I3 I 0.31243(2) 0.56032(2) 0.76073(2) 0.01863(4) Uani 1 1 d . . . . .
N1 N 0.2374(2) 0.54995(16) 0.30377(14) 0.0139(3) Uani 1 1 d . . . . .
C1 C 0.1883(2) 0.44552(19) 0.30775(18) 0.0146(4) Uani 1 1 d . . . . .
C2 C 0.1638(3) 0.4413(2) 0.20086(18) 0.0177(4) Uani 1 1 d . . . . .
H2 H 0.124126 0.370292 0.203926 0.021 Uiso 1 1 calc R . . . .
C3 C 0.1973(3) 0.5407(2) 0.09009(19) 0.0192(4) Uani 1 1 d . . . . .
H3 H 0.185729 0.537025 0.016386 0.023 Uiso 1 1 calc R . . . .
C4 C 0.2478(3) 0.6450(2) 0.08822(18) 0.0178(4) Uani 1 1 d . . . . .
H4 H 0.271822 0.713522 0.012603 0.021 Uiso 1 1 calc R . . . .
C5 C 0.2640(2) 0.65099(19) 0.19558(18) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.1647(3) 0.3418(2) 0.42180(18) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.1495(2) 0.25058(19) 0.51544(18) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.1294(2) 0.13914(19) 0.62433(18) 0.0166(4) Uani 1 1 d . . . . .
C9 C 0.1450(3) 0.1318(2) 0.73909(18) 0.0177(4) Uani 1 1 d . . . . .
C10 C 0.1182(3) 0.0223(2) 0.84209(19) 0.0227(5) Uani 1 1 d . . . . .
H10 H 0.128254 0.016992 0.919888 0.027 Uiso 1 1 calc R . . . .
C11 C 0.0767(3) -0.0794(2) 0.8315(2) 0.0266(5) Uani 1 1 d . . . . .
H11 H 0.055510 -0.153219 0.902625 0.032 Uiso 1 1 calc R . . . .
C12 C 0.0657(3) -0.0749(2) 0.7184(2) 0.0255(5) Uani 1 1 d . . . . .
H12 H 0.040510 -0.145870 0.711729 0.031 Uiso 1 1 calc R . . . .
C13 C 0.0919(3) 0.0340(2) 0.6155(2) 0.0213(4) Uani 1 1 d . . . . .
H13 H 0.084387 0.037645 0.537908 0.026 Uiso 1 1 calc R . . . .
C14 C 0.3034(2) 0.7607(2) 0.19773(18) 0.0165(4) Uani 1 1 d . . . . .
C15 C 0.3302(2) 0.8557(2) 0.19824(17) 0.0163(4) Uani 1 1 d . . . . .
C16 C 0.3664(2) 0.96880(19) 0.19680(18) 0.0159(4) Uani 1 1 d . . . . .
C17 C 0.3706(3) 1.0777(2) 0.08763(19) 0.0182(4) Uani 1 1 d . . . . .
H17 H 0.348448 1.075532 0.015683 0.022 Uiso 1 1 calc R . . . .
C18 C 0.4065(3) 1.1881(2) 0.0836(2) 0.0215(4) Uani 1 1 d . . . . .
H18 H 0.405922 1.261858 0.009858 0.026 Uiso 1 1 calc R . . . .
C19 C 0.4434(3) 1.1905(2) 0.1880(2) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.473016 1.265089 0.184520 0.027 Uiso 1 1 calc R . . . .
C20 C 0.4372(3) 1.0842(2) 0.2976(2) 0.0214(4) Uani 1 1 d . . . . .
H20 H 0.460623 1.087140 0.368927 0.026 Uiso 1 1 calc R . . . .
C21 C 0.3970(3) 0.9742(2) 0.30300(18) 0.0171(4) Uani 1 1 d . . . . .
C22 C 0.2682(3) 0.5532(2) 0.41734(18) 0.0191(4) Uani 1 1 d . . . . .
H22A H 0.379950 0.579548 0.404553 0.029 Uiso 1 1 calc GR . . . .
H22B H 0.266382 0.469018 0.483537 0.029 Uiso 1 1 calc GR . . . .
H22C H 0.178593 0.613192 0.438831 0.029 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C9 2.108(2) . ?
I2 C21 2.100(2) . ?
N1 C1 1.362(3) . ?
N1 C5 1.366(3) . ?
N1 C22 1.486(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.420(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.385(3) . ?
C5 C14 1.421(3) . ?
C6 C7 1.198(3) . ?
C7 C8 1.428(3) . ?
C8 C9 1.405(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.382(3) . ?
C14 C15 1.198(3) . ?
C15 C16 1.430(3) . ?
C16 C17 1.405(3) . ?
C16 C21 1.408(3) . ?
C17 C18 1.383(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.393(3) . ?
C20 C21 1.387(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
C1 N1 C5 120.75(17) . . ?
C1 N1 C22 120.00(16) . . ?
C5 N1 C22 119.21(17) . . ?
N1 C1 C2 119.95(18) . . ?
N1 C1 C6 118.95(18) . . ?
C2 C1 C6 121.10(19) . . ?
C3 C2 C1 119.9(2) . . ?
C4 C3 C2 119.07(19) . . ?
C3 C4 C5 120.61(19) . . ?
N1 C5 C4 119.59(19) . . ?
N1 C5 C14 118.32(18) . . ?
C4 C5 C14 122.07(18) . . ?
C7 C6 C1 176.8(2) . . ?
C6 C7 C8 177.5(2) . . ?
C9 C8 C7 122.43(19) . . ?
C13 C8 C7 118.33(19) . . ?
C13 C8 C9 119.24(19) . . ?
C8 C9 I1 120.18(15) . . ?
C10 C9 I1 120.12(16) . . ?
C10 C9 C8 119.7(2) . . ?
C11 C10 C9 120.0(2) . . ?
C10 C11 C12 120.9(2) . . ?
C13 C12 C11 119.3(2) . . ?
C12 C13 C8 120.8(2) . . ?
C15 C14 C5 177.3(2) . . ?
C14 C15 C16 178.4(2) . . ?
C17 C16 C15 119.68(18) . . ?
C17 C16 C21 118.86(19) . . ?
C21 C16 C15 121.45(18) . . ?
C18 C17 C16 120.8(2) . . ?
C17 C18 C19 119.6(2) . . ?
C18 C19 C20 120.5(2) . . ?
C21 C20 C19 120.1(2) . . ?
C16 C21 I2 120.65(15) . . ?
C20 C21 I2 119.33(15) . . ?
C20 C21 C16 119.99(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umt_ob149
_database_code_depnum_ccdc_archive 'CCDC 2075099'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2020-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 I2 N, C F3 O3 S'
_chemical_formula_sum            'C23 H14 F3 I2 N O3 S'
_chemical_formula_weight         695.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5783(4)
_cell_length_b                   11.1636(6)
_cell_length_c                   13.3063(7)
_cell_angle_alpha                74.307(2)
_cell_angle_beta                 71.324(2)
_cell_angle_gamma                79.269(2)
_cell_volume                     1155.23(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9051
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.715
_cell_measurement_theta_min      2.804
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.283
_exptl_absorpt_coefficient_mu    2.863
_exptl_absorpt_correction_T_max  0.6037
_exptl_absorpt_correction_T_min  0.4467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0746 before and 0.0561 after correction. The Ratio of minimum to maximum transmission is 0.7399. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36937
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.759
_diffrn_reflns_theta_min         2.521
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4802
_reflns_number_total             5990
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (BRUKER, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0126P)²+1.9348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0474
_refine_ls_wR_factor_ref         0.0517
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.90176(2) 0.26869(2) 0.42900(2) 0.01437(5) Uani 1 1 d . . . . .
I2 I 0.29462(2) 0.50110(2) 0.80800(2) 0.01591(5) Uani 1 1 d . . . . .
S1 S 0.54082(9) 0.20019(7) 0.70616(6) 0.01737(15) Uani 1 1 d . . . . .
F1 F 0.7078(2) 0.06187(17) 0.84038(16) 0.0281(4) Uani 1 1 d . . . . .
F2 F 0.5737(2) 0.23043(17) 0.88750(14) 0.0253(4) Uani 1 1 d . . . . .
F3 F 0.4432(2) 0.07419(18) 0.90893(14) 0.0293(4) Uani 1 1 d . . . . .
O1 O 0.6711(3) 0.2799(2) 0.65231(18) 0.0329(6) Uani 1 1 d . . . . .
O2 O 0.3758(3) 0.2649(2) 0.72855(18) 0.0266(5) Uani 1 1 d . . . . .
O3 O 0.5576(3) 0.0894(2) 0.66629(18) 0.0310(6) Uani 1 1 d . . . . .
N1 N 0.7520(3) 0.7090(2) 0.46853(18) 0.0118(5) Uani 1 1 d . . . . .
C1 C 0.8817(3) 0.7260(3) 0.3760(2) 0.0141(6) Uani 1 1 d . . . . .
C2 C 0.9301(4) 0.8453(3) 0.3272(2) 0.0161(6) Uani 1 1 d . . . . .
H2 H 1.017324 0.858226 0.261208 0.019 Uiso 1 1 calc R . . . .
C3 C 0.8524(4) 0.9451(3) 0.3738(2) 0.0158(6) Uani 1 1 d . . . . .
H3 H 0.885356 1.026571 0.340231 0.019 Uiso 1 1 calc R . . . .
C4 C 0.7253(3) 0.9248(3) 0.4704(2) 0.0149(6) Uani 1 1 d . . . . .
H4 H 0.673039 0.992093 0.504684 0.018 Uiso 1 1 calc R . . . .
C5 C 0.6748(3) 0.8061(3) 0.5168(2) 0.0127(5) Uani 1 1 d . . . . .
C6 C 0.9652(3) 0.6208(3) 0.3325(2) 0.0140(6) Uani 1 1 d . . . . .
C7 C 1.0426(3) 0.5350(3) 0.2938(2) 0.0133(6) Uani 1 1 d . . . . .
C8 C 1.1341(3) 0.4350(3) 0.2435(2) 0.0132(6) Uani 1 1 d . . . . .
C9 C 1.0928(3) 0.3109(3) 0.2845(2) 0.0135(6) Uani 1 1 d . . . . .
C10 C 1.1824(4) 0.2172(3) 0.2325(2) 0.0176(6) Uani 1 1 d . . . . .
H10 H 1.155590 0.133525 0.261226 0.021 Uiso 1 1 calc R . . . .
C11 C 1.3115(4) 0.2456(3) 0.1383(2) 0.0197(6) Uani 1 1 d . . . . .
H11 H 1.370642 0.181627 0.101374 0.024 Uiso 1 1 calc R . . . .
C12 C 1.3547(4) 0.3667(3) 0.0977(2) 0.0183(6) Uani 1 1 d . . . . .
H12 H 1.444426 0.385122 0.033828 0.022 Uiso 1 1 calc R . . . .
C13 C 1.2682(3) 0.4604(3) 0.1494(2) 0.0150(6) Uani 1 1 d . . . . .
H13 H 1.299416 0.542978 0.121388 0.018 Uiso 1 1 calc R . . . .
C14 C 0.5447(3) 0.7836(3) 0.6157(2) 0.0146(6) Uani 1 1 d . . . . .
C15 C 0.4378(4) 0.7746(3) 0.7006(2) 0.0150(6) Uani 1 1 d . . . . .
C16 C 0.3113(3) 0.7734(3) 0.8020(2) 0.0140(6) Uani 1 1 d . . . . .
C17 C 0.2288(3) 0.6682(3) 0.8615(2) 0.0151(6) Uani 1 1 d . . . . .
C18 C 0.1055(4) 0.6740(3) 0.9582(2) 0.0202(6) Uani 1 1 d . . . . .
H18 H 0.045787 0.603969 0.997113 0.024 Uiso 1 1 calc R . . . .
C19 C 0.0689(4) 0.7815(3) 0.9985(3) 0.0241(7) Uani 1 1 d . . . . .
H19 H -0.015416 0.784659 1.064829 0.029 Uiso 1 1 calc R . . . .
C20 C 0.1553(4) 0.8844(3) 0.9421(3) 0.0231(7) Uani 1 1 d . . . . .
H20 H 0.132390 0.956979 0.970921 0.028 Uiso 1 1 calc R . . . .
C21 C 0.2747(4) 0.8812(3) 0.8439(2) 0.0175(6) Uani 1 1 d . . . . .
H21 H 0.332153 0.952339 0.804609 0.021 Uiso 1 1 calc R . . . .
C22 C 0.6950(4) 0.5821(3) 0.5161(2) 0.0169(6) Uani 1 1 d . . . . .
H22A H 0.781599 0.524270 0.542765 0.025 Uiso 1 1 calc GR . . . .
H22B H 0.671991 0.552085 0.460049 0.025 Uiso 1 1 calc GR . . . .
H22C H 0.594064 0.586370 0.576617 0.025 Uiso 1 1 calc GR . . . .
C23 C 0.5678(4) 0.1388(3) 0.8422(2) 0.0164(6) 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
I1 C9 2.094(3) . ?
I2 C17 2.092(3) . ?
S1 O1 1.438(2) . ?
S1 O2 1.442(2) . ?
S1 O3 1.440(2) . ?
S1 C23 1.827(3) . ?
F1 C23 1.337(3) . ?
F2 C23 1.336(3) . ?
F3 C23 1.335(3) . ?
N1 C1 1.365(4) . ?
N1 C5 1.365(3) . ?
N1 C22 1.490(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.421(4) . ?
C2 C3 1.378(4) . ?
C3 C4 1.389(4) . ?
C4 C5 1.387(4) . ?
C5 C14 1.424(4) . ?
C6 C7 1.197(4) . ?
C7 C8 1.433(4) . ?
C8 C9 1.412(4) . ?
C8 C13 1.407(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.375(4) . ?
C14 C15 1.198(4) . ?
C15 C16 1.434(4) . ?
C16 C17 1.398(4) . ?
C16 C21 1.403(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.387(4) . ?
C19 C20 1.388(5) . ?
C20 C21 1.383(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
O1 S1 O2 114.93(15) . . ?
O1 S1 O3 115.93(15) . . ?
O1 S1 C23 102.97(14) . . ?
O2 S1 C23 102.53(13) . . ?
O3 S1 O2 114.42(14) . . ?
O3 S1 C23 103.50(13) . . ?
C1 N1 C22 118.8(2) . . ?
C5 N1 C1 120.9(2) . . ?
C5 N1 C22 120.3(2) . . ?
N1 C1 C2 119.5(2) . . ?
N1 C1 C6 119.0(2) . . ?
C2 C1 C6 121.5(3) . . ?
C3 C2 C1 120.5(3) . . ?
C2 C3 C4 119.1(3) . . ?
C5 C4 C3 119.9(3) . . ?
N1 C5 C4 120.0(3) . . ?
N1 C5 C14 119.3(2) . . ?
C4 C5 C14 120.7(3) . . ?
C7 C6 C1 176.7(3) . . ?
C6 C7 C8 177.7(3) . . ?
C9 C8 C7 122.1(3) . . ?
C13 C8 C7 119.5(3) . . ?
C13 C8 C9 118.4(3) . . ?
C8 C9 I1 119.2(2) . . ?
C10 C9 I1 120.4(2) . . ?
C10 C9 C8 120.4(3) . . ?
C9 C10 C11 120.0(3) . . ?
C12 C11 C10 120.3(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C8 120.6(3) . . ?
C15 C14 C5 173.9(3) . . ?
C14 C15 C16 175.7(3) . . ?
C17 C16 C15 122.6(3) . . ?
C17 C16 C21 119.5(3) . . ?
C21 C16 C15 117.9(3) . . ?
C16 C17 I2 120.4(2) . . ?
C18 C17 I2 119.9(2) . . ?
C18 C17 C16 119.7(3) . . ?
C19 C18 C17 120.4(3) . . ?
C18 C19 C20 120.2(3) . . ?
C21 C20 C19 119.9(3) . . ?
C20 C21 C16 120.3(3) . . ?
F1 C23 S1 111.9(2) . . ?
F2 C23 S1 111.68(19) . . ?
F2 C23 F1 107.2(2) . . ?
F3 C23 S1 111.3(2) . . ?
F3 C23 F1 107.2(2) . . ?
F3 C23 F2 107.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umt_ob214a
_database_code_depnum_ccdc_archive 'CCDC 2075100'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2020-09-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 I2 N2, I'
_chemical_formula_sum            'C22 H15 I3 N2'
_chemical_formula_weight         688.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   21.0883(17)
_cell_length_b                   13.7730(11)
_cell_length_c                   7.3022(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2120.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9492
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.914
_cell_measurement_theta_min      2.958
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.173
_exptl_absorpt_coefficient_mu    4.430
_exptl_absorpt_correction_T_max  0.6483
_exptl_absorpt_correction_T_min  0.5018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0689 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.7740. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            29568
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         2.958
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2368
_reflns_number_total             3244
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.329
_refine_diff_density_min         -1.211
_refine_diff_density_rms         0.178
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+5.0072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3. Others
 Fixed Sof: H12A(0.5) H12B(0.5) H12C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11)
4.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.64476(2) 0.68497(2) 0.34962(3) 0.01598(7) Uani 1 1 d . . . . .
N1 N 0.500000 0.5095(4) 0.250000 0.0185(10) Uani 1 2 d DS T P . .
H1 H 0.4655(13) 0.539(3) 0.239(6) 0.018(12) Uiso 1 1 d D . . . .
N2 N 0.500000 0.2097(3) 0.250000 0.0158(9) Uani 1 2 d S T P . .
C1 C 0.72434(17) 0.5996(3) 0.4160(5) 0.0145(8) Uani 1 1 d . . . . .
C2 C 0.78084(19) 0.6425(3) 0.4688(6) 0.0180(8) Uani 1 1 d . . . . .
H2 H 0.783834 0.711250 0.474463 0.022 Uiso 1 1 calc R . . . .
C3 C 0.8327(2) 0.5866(3) 0.5132(5) 0.0194(8) Uani 1 1 d . . . . .
H3 H 0.870912 0.616898 0.551845 0.023 Uiso 1 1 calc R . . . .
C4 C 0.82948(19) 0.4864(3) 0.5019(5) 0.0189(8) Uani 1 1 d . . . . .
H4 H 0.865713 0.448120 0.529632 0.023 Uiso 1 1 calc R . . . .
C5 C 0.77354(18) 0.4421(3) 0.4504(6) 0.0176(8) Uani 1 1 d . . . . .
H5 H 0.771403 0.373338 0.443489 0.021 Uiso 1 1 calc R . . . .
C6 C 0.71972(18) 0.4979(3) 0.4080(5) 0.0143(7) Uani 1 1 d . . . . .
C7 C 0.66165(18) 0.4501(3) 0.3609(5) 0.0150(7) Uani 1 1 d . . . . .
C8 C 0.61394(18) 0.4069(3) 0.3267(5) 0.0138(7) Uani 1 1 d . . . . .
C9 C 0.55596(18) 0.3584(3) 0.2882(5) 0.0138(8) Uani 1 1 d . . . . .
C10 C 0.500000 0.4119(4) 0.250000 0.0129(10) Uani 1 2 d S T P . .
C11 C 0.55372(18) 0.2586(3) 0.2864(5) 0.0147(8) Uani 1 1 d . . . . .
H11 H 0.591327 0.223053 0.311689 0.018 Uiso 1 1 calc R . . . .
C12 C 0.500000 0.1015(4) 0.250000 0.0219(13) Uani 1 2 d S T P . .
H12A H 0.514331 0.077781 0.369571 0.033 Uiso 0.5 1 calc GR . . A -1
H12B H 0.528691 0.077781 0.154372 0.033 Uiso 0.5 1 calc GR . . A -1
H12C H 0.456978 0.077781 0.226057 0.033 Uiso 0.5 1 calc GR . . A -1
I2 I 0.500000 0.81666(3) 0.250000 0.02004(9) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.106(4) . ?
N1 C10 1.344(7) . ?
N2 C11 1.344(4) 3_655 ?
N2 C11 1.344(4) . ?
N2 C12 1.491(7) . ?
C1 C2 1.385(5) . ?
C1 C6 1.405(5) . ?
C2 C3 1.377(6) . ?
C3 C4 1.384(6) . ?
C4 C5 1.380(6) . ?
C5 C6 1.405(5) . ?
C6 C7 1.432(5) . ?
C7 C8 1.195(5) . ?
C8 C9 1.422(5) . ?
C9 C10 1.419(5) . ?
C9 C11 1.376(5) . ?

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
C11 N2 C11 119.9(5) 3_655 . ?
C11 N2 C12 120.0(2) 3_655 . ?
C11 N2 C12 120.0(2) . . ?
C2 C1 I1 120.8(3) . . ?
C2 C1 C6 119.8(4) . . ?
C6 C1 I1 119.5(3) . . ?
C3 C2 C1 120.7(4) . . ?
C2 C3 C4 120.3(4) . . ?
C5 C4 C3 119.9(4) . . ?
C4 C5 C6 120.6(4) . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 121.8(4) . . ?
C5 C6 C7 119.5(3) . . ?
C8 C7 C6 177.1(4) . . ?
C7 C8 C9 178.0(4) . . ?
C10 C9 C8 120.7(4) . . ?
C11 C9 C8 120.1(4) . . ?
C11 C9 C10 119.2(4) . . ?
N1 C10 C9 121.3(2) . . ?
N1 C10 C9 121.3(2) . 3_655 ?
C9 C10 C9 117.4(5) . 3_655 ?
N2 C11 C9 122.1(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umt_ob175
_database_code_depnum_ccdc_archive 'CCDC 2075105'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2020-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 I2 N, I'
_chemical_formula_sum            'C22 H14 I3 N'
_chemical_formula_weight         673.04
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   21.0383(12)
_cell_length_b                   13.7820(8)
_cell_length_c                   7.3031(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2117.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.556
_cell_measurement_theta_min      2.956
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.240
_exptl_absorpt_coefficient_mu    4.434
_exptl_absorpt_correction_T_max  0.5640
_exptl_absorpt_correction_T_min  0.4356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0626 before and 0.0559 after correction. The Ratio of minimum to maximum transmission is 0.7723. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.111
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            44308
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.606
_diffrn_reflns_theta_min         2.956
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2354
_reflns_number_total             2984
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (BRUKER, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0207P)²+1.4477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0446
_refine_ls_wR_factor_ref         0.0484
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H12A(0.5) H12B(0.5) H12C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.35678(2) 0.68214(2) 0.65645(2) 0.01439(5) Uani 1 1 d . . . . .
I2 I 0.500000 0.82437(2) 0.750000 0.01423(6) Uani 1 2 d S T P . .
N1 N 0.500000 0.2069(2) 0.750000 0.0108(6) Uani 1 2 d S T P . .
C1 C 0.44572(13) 0.25409(19) 0.7183(3) 0.0134(5) Uani 1 1 d . . . . .
H1 H 0.407820 0.218369 0.696926 0.016 Uiso 1 1 calc R . . . .
C2 C 0.44398(13) 0.35564(19) 0.7161(4) 0.0134(6) Uani 1 1 d . . . . .
C3 C 0.500000 0.4057(3) 0.750000 0.0138(8) Uani 1 2 d S T P . .
H3 H 0.500000 0.474640 0.750003 0.017 Uiso 1 2 calc RS T P . .
C4 C 0.38556(13) 0.4040(2) 0.6801(4) 0.0152(6) Uani 1 1 d . . . . .
C5 C 0.33748(13) 0.44700(19) 0.6468(4) 0.0135(5) Uani 1 1 d . . . . .
C6 C 0.27968(13) 0.4963(2) 0.5994(3) 0.0127(5) Uani 1 1 d . . . . .
C7 C 0.27642(12) 0.5978(2) 0.5893(3) 0.0132(6) Uani 1 1 d . . . . .
C8 C 0.22039(14) 0.6427(2) 0.5335(4) 0.0162(6) Uani 1 1 d . . . . .
H8 H 0.218262 0.711493 0.526308 0.019 Uiso 1 1 calc R . . . .
C9 C 0.16775(13) 0.5872(2) 0.4886(4) 0.0173(6) Uani 1 1 d . . . . .
H9 H 0.130014 0.618075 0.447111 0.021 Uiso 1 1 calc R . . . .
C10 C 0.16975(13) 0.4868(2) 0.5037(4) 0.0186(6) Uani 1 1 d . . . . .
H10 H 0.133017 0.449317 0.476943 0.022 Uiso 1 1 calc R . . . .
C11 C 0.22527(13) 0.4416(2) 0.5576(4) 0.0161(6) Uani 1 1 d . . . . .
H11 H 0.226653 0.372868 0.566476 0.019 Uiso 1 1 calc R . . . .
C12 C 0.500000 0.0993(3) 0.750000 0.0162(8) Uani 1 2 d S T P . .
H12A H 0.471276 0.075628 0.845703 0.024 Uiso 0.5 1 calc GR . . A -1
H12B H 0.543133 0.075628 0.773809 0.024 Uiso 0.5 1 calc GR . . A -1
H12C H 0.485591 0.075628 0.630488 0.024 Uiso 0.5 1 calc GR . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.109(3) . ?
N1 C1 1.334(3) 3_656 ?
N1 C1 1.334(3) . ?
N1 C12 1.482(5) . ?
C1 C2 1.400(4) . ?
C2 C3 1.388(3) . ?
C2 C4 1.423(4) . ?
C4 C5 1.197(4) . ?
C5 C6 1.435(4) . ?
C6 C7 1.403(4) . ?
C6 C11 1.404(4) . ?
C7 C8 1.392(4) . ?
C8 C9 1.386(4) . ?
C9 C10 1.389(4) . ?
C10 C11 1.381(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
C1 N1 C1 121.7(3) . 3_656 ?
C1 N1 C12 119.17(16) . . ?
C1 N1 C12 119.17(16) 3_656 . ?
N1 C1 C2 120.8(3) . . ?
C1 C2 C4 119.5(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C4 122.2(3) . . ?
C2 C3 C2 120.4(3) . 3_656 ?
C5 C4 C2 177.9(3) . . ?
C4 C5 C6 177.5(3) . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 C11 118.9(2) . . ?
C11 C6 C5 119.3(2) . . ?
C6 C7 I1 119.88(19) . . ?
C8 C7 I1 120.1(2) . . ?
C8 C7 C6 120.0(3) . . ?
C9 C8 C7 120.0(3) . . ?
C8 C9 C10 120.5(3) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 C6 120.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umt_ob206
_database_code_depnum_ccdc_archive 'CCDC 2075104'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2021-04-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 I2 N, C F3 O3 S'
_chemical_formula_sum            'C24 H16 F3 I2 N O3 S'
_chemical_formula_weight         709.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2077(5)
_cell_length_b                   12.3954(8)
_cell_length_c                   14.0967(9)
_cell_angle_alpha                98.565(2)
_cell_angle_beta                 101.823(2)
_cell_angle_gamma                91.413(2)
_cell_volume                     1216.98(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.375
_cell_measurement_theta_min      2.892
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.561
_exptl_absorpt_coefficient_mu    2.720
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0647 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8422.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            64454
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_min         2.892
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              fine-focus
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4864
_reflns_number_total             5808
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.559
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5808
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²+3.0924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0683
_refine_special_details          ?
# start Validation Reply Form
_vrf_PLAT230_umt_ob206           
;
PROBLEM: Hirshfeld Test Diff for    C5       --C6       .        8.0 s.u.  
RESPONSE: The position at C5 seems to be a site that has some small amount
of unknown disorder causing this error. The material that was crystalized 
showed no indications of decomposition or a secondary side product species
via NMR or MS.  
;
# end Validation Reply Form
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C5 \\sim C4 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
3. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C18(H18), C19(H19),
 C20(H20), C21(H21)
4.b Fitted hexagon refined as free rotating group:
 C5(C6,C1,C2,C3,C4)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.74950(3) 0.19140(2) 0.40404(2) 0.01557(6) Uani 1 1 d . . . . .
I2 I 0.72051(4) 0.48717(2) 0.86962(2) 0.03141(8) Uani 1 1 d . . . . .
N1 N 0.7561(4) 0.7974(2) 0.4718(2) 0.0148(6) Uani 1 1 d . . . . .
C5 C 0.7991(3) 0.35801(13) 0.15680(16) 0.0180(7) Uani 1 1 d G U . . .
H5 H 0.800404 0.431183 0.144211 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7799(3) 0.33630(14) 0.24836(14) 0.0164(7) Uani 1 1 d G U . . .
C1 C 0.7780(3) 0.22924(17) 0.26679(12) 0.0153(7) Uani 1 1 d G . . . .
C2 C 0.7953(3) 0.14388(12) 0.19365(16) 0.0180(7) Uani 1 1 d G . . . .
H2 H 0.793959 0.070704 0.206239 0.022 Uiso 1 1 calc R U . . .
C3 C 0.8144(4) 0.16558(15) 0.10209(14) 0.0214(7) Uani 1 1 d G . . . .
H3 H 0.826233 0.107241 0.052099 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8164(3) 0.27265(18) 0.08366(13) 0.0215(8) Uani 1 1 d G U . . .
H4 H 0.829455 0.287480 0.021084 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7669(5) 0.4265(3) 0.3250(3) 0.0152(7) Uani 1 1 d . . . . .
C8 C 0.7633(5) 0.5055(3) 0.3850(3) 0.0163(7) Uani 1 1 d . . . . .
C9 C 0.7574(4) 0.6039(3) 0.4513(3) 0.0137(7) Uani 1 1 d . . . . .
C10 C 0.7438(4) 0.6042(3) 0.5496(3) 0.0146(7) Uani 1 1 d . . . . .
C11 C 0.7637(5) 0.7020(3) 0.4146(3) 0.0148(7) Uani 1 1 d . . . . .
H11 H 0.773396 0.701088 0.348338 0.018 Uiso 1 1 calc R U . . .
C12 C 0.7427(5) 0.8016(3) 0.5661(3) 0.0158(7) Uani 1 1 d . . . . .
H12 H 0.736938 0.870436 0.604927 0.019 Uiso 1 1 calc R U . . .
C13 C 0.7371(5) 0.7072(3) 0.6076(3) 0.0156(7) Uani 1 1 d . . . . .
C14 C 0.7228(5) 0.7156(3) 0.7078(3) 0.0168(7) Uani 1 1 d . . . . .
C15 C 0.7106(5) 0.7226(3) 0.7916(3) 0.0176(7) Uani 1 1 d . . . . .
C16 C 0.6981(5) 0.7349(3) 0.8933(3) 0.0182(7) Uani 1 1 d . . . . .
C17 C 0.7037(5) 0.6456(3) 0.9432(3) 0.0233(8) Uani 1 1 d . . . . .
C18 C 0.6909(6) 0.6609(4) 1.0416(3) 0.0309(9) Uani 1 1 d . . . . .
H18 H 0.697366 0.600206 1.075879 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6687(6) 0.7642(4) 1.0895(3) 0.0312(9) Uani 1 1 d . . . . .
H19 H 0.658136 0.773830 1.156272 0.037 Uiso 1 1 calc R U . . .
C20 C 0.6619(6) 0.8530(4) 1.0409(3) 0.0283(9) Uani 1 1 d . . . . .
H20 H 0.645690 0.923563 1.074004 0.034 Uiso 1 1 calc R U . . .
C21 C 0.6787(5) 0.8393(3) 0.9437(3) 0.0216(8) Uani 1 1 d . . . . .
H21 H 0.677011 0.901023 0.910916 0.026 Uiso 1 1 calc R U . . .
C22 C 0.7354(5) 0.5015(3) 0.5917(3) 0.0201(7) Uani 1 1 d . . . . .
H22A H 0.714959 0.438782 0.538671 0.030 Uiso 1 1 calc R U . . .
H22B H 0.630506 0.502458 0.626307 0.030 Uiso 1 1 calc R U . . .
H22C H 0.855241 0.495590 0.637715 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7691(5) 0.9002(3) 0.4314(3) 0.0201(7) Uani 1 1 d . . . . .
H23A H 0.744877 0.961702 0.478725 0.030 Uiso 1 1 calc R U . . .
H23B H 0.674557 0.896045 0.369919 0.030 Uiso 1 1 calc R U . . .
H23C H 0.896430 0.910839 0.418680 0.030 Uiso 1 1 calc R U . . .
S1 S 0.75649(13) 0.19088(8) 0.68626(7) 0.02081(19) Uani 1 1 d . . . . .
F1 F 0.8273(4) 0.1522(3) 0.86777(18) 0.0496(8) Uani 1 1 d . . . . .
F2 F 0.6040(4) 0.0479(2) 0.7711(2) 0.0481(7) Uani 1 1 d . . . . .
F3 F 0.8934(5) 0.0229(2) 0.7642(2) 0.0605(9) Uani 1 1 d . . . . .
O1 O 0.6110(4) 0.2611(2) 0.7086(2) 0.0333(7) Uani 1 1 d . . . . .
O2 O 0.9442(4) 0.2406(3) 0.7049(2) 0.0427(8) Uani 1 1 d . . . . .
O3 O 0.7024(5) 0.1155(3) 0.5953(2) 0.0363(7) Uani 1 1 d . . . . .
C24 C 0.7712(6) 0.0990(3) 0.7771(3) 0.0286(9) 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
I1 C1 2.1057(16) . ?
I2 C17 2.098(4) . ?
N1 C11 1.337(4) . ?
N1 C12 1.345(5) . ?
N1 C23 1.479(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.3900 . ?
C5 C4 1.3900 . ?
C6 C1 1.3900 . ?
C6 C7 1.454(4) . ?
C1 C2 1.3900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C4 1.3900 . ?
C4 H4 0.9500 . ?
C7 C8 1.199(5) . ?
C8 C9 1.430(5) . ?
C9 C10 1.409(5) . ?
C9 C11 1.393(5) . ?
C10 C13 1.418(5) . ?
C10 C22 1.486(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.387(5) . ?
C13 C14 1.426(5) . ?
C14 C15 1.192(5) . ?
C15 C16 1.441(5) . ?
C16 C17 1.395(5) . ?
C16 C21 1.405(5) . ?
C17 C18 1.393(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
S1 O1 1.434(3) . ?
S1 O2 1.430(3) . ?
S1 O3 1.446(3) . ?
S1 C24 1.825(4) . ?
F1 C24 1.325(5) . ?
F2 C24 1.328(5) . ?
F3 C24 1.325(5) . ?

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
C11 N1 C12 121.1(3) . . ?
C11 N1 C23 119.3(3) . . ?
C12 N1 C23 119.6(3) . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.48(19) . . ?
C1 C6 C5 120.0 . . ?
C1 C6 C7 120.50(19) . . ?
C6 C1 I1 121.70(11) . . ?
C2 C1 I1 118.30(11) . . ?
C2 C1 C6 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C8 C7 C6 175.3(4) . . ?
C7 C8 C9 176.2(4) . . ?
C10 C9 C8 122.6(3) . . ?
C11 C9 C8 117.2(3) . . ?
C11 C9 C10 120.2(3) . . ?
C9 C10 C13 117.1(3) . . ?
C9 C10 C22 122.1(3) . . ?
C13 C10 C22 120.8(3) . . ?
N1 C11 C9 120.7(3) . . ?
N1 C11 H11 119.6 . . ?
C9 C11 H11 119.6 . . ?
N1 C12 H12 119.4 . . ?
N1 C12 C13 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C10 C13 C14 121.2(3) . . ?
C12 C13 C10 119.6(3) . . ?
C12 C13 C14 119.3(3) . . ?
C15 C14 C13 179.9(5) . . ?
C14 C15 C16 178.1(4) . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 C21 118.9(3) . . ?
C21 C16 C15 119.4(3) . . ?
C16 C17 I2 120.4(3) . . ?
C18 C17 I2 119.7(3) . . ?
C18 C17 C16 119.9(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 S1 O3 114.66(19) . . ?
O1 S1 C24 102.73(19) . . ?
O2 S1 O1 116.2(2) . . ?
O2 S1 O3 115.0(2) . . ?
O2 S1 C24 103.7(2) . . ?
O3 S1 C24 101.73(19) . . ?
F1 C24 S1 111.7(3) . . ?
F1 C24 F2 107.7(4) . . ?
F2 C24 S1 111.2(3) . . ?
F3 C24 S1 111.5(3) . . ?
F3 C24 F1 107.3(3) . . ?
F3 C24 F2 107.2(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
I1 C1 C2 C3 -179.97(16) . . . . ?
I2 C17 C18 C19 -176.3(3) . . . . ?
N1 C12 C13 C10 -0.6(5) . . . . ?
N1 C12 C13 C14 -180.0(3) . . . . ?
C5 C6 C1 I1 179.97(16) . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 178.4(2) . . . . ?
C7 C6 C1 I1 1.6(2) . . . . ?
C7 C6 C1 C2 -178.4(2) . . . . ?
C8 C9 C10 C13 -179.3(3) . . . . ?
C8 C9 C10 C22 0.3(5) . . . . ?
C8 C9 C11 N1 179.0(3) . . . . ?
C9 C10 C13 C12 0.5(5) . . . . ?
C9 C10 C13 C14 179.9(3) . . . . ?
C10 C9 C11 N1 -0.3(5) . . . . ?
C11 N1 C12 C13 0.3(5) . . . . ?
C11 C9 C10 C13 -0.1(5) . . . . ?
C11 C9 C10 C22 179.6(3) . . . . ?
C12 N1 C11 C9 0.2(5) . . . . ?
C15 C16 C17 I2 -2.3(5) . . . . ?
C15 C16 C17 C18 -179.9(4) . . . . ?
C15 C16 C21 C20 178.5(3) . . . . ?
C16 C17 C18 C19 1.3(6) . . . . ?
C17 C16 C21 C20 -1.2(5) . . . . ?
C17 C18 C19 C20 -0.9(6) . . . . ?
C18 C19 C20 C21 -0.5(6) . . . . ?
C19 C20 C21 C16 1.5(6) . . . . ?
C21 C16 C17 I2 177.3(3) . . . . ?
C21 C16 C17 C18 -0.3(5) . . . . ?
C22 C10 C13 C12 -179.2(3) . . . . ?
C22 C10 C13 C14 0.2(5) . . . . ?
C23 N1 C11 C9 178.1(3) . . . . ?
C23 N1 C12 C13 -177.7(3) . . . . ?
O1 S1 C24 F1 -63.5(3) . . . . ?
O1 S1 C24 F2 56.9(3) . . . . ?
O1 S1 C24 F3 176.5(3) . . . . ?
O2 S1 C24 F1 57.9(4) . . . . ?
O2 S1 C24 F2 178.3(3) . . . . ?
O2 S1 C24 F3 -62.1(4) . . . . ?
O3 S1 C24 F1 177.5(3) . . . . ?
O3 S1 C24 F2 -62.1(3) . . . . ?
O3 S1 C24 F3 57.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umt_ob191
_database_code_depnum_ccdc_archive 'CCDC 2075103'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2021-04-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 I2 N, C F3 O3 S'
_chemical_formula_sum            'C23 H14 F3 I2 N O3 S'
_chemical_formula_weight         695.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.1362(3)
_cell_length_b                   12.3559(6)
_cell_length_c                   14.2656(7)
_cell_angle_alpha                98.460(2)
_cell_angle_beta                 103.067(2)
_cell_angle_gamma                94.936(2)
_cell_volume                     1202.63(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9342
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.622
_cell_measurement_theta_min      2.953
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    2.750
_exptl_absorpt_correction_T_max  0.4935
_exptl_absorpt_correction_T_min  0.3601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0747 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.7297.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            86479
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         2.953
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_type              fine-focus
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5332
_reflns_number_total             5965
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.148
_refine_diff_density_min         -1.406
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5965
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0136P)²+5.2915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0678
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.25641(3) 0.18596(2) 0.40948(2) 0.01386(5) Uani 1 1 d . . . . .
I2 I 0.20482(4) 0.47185(2) 0.83851(2) 0.02706(7) Uani 1 1 d . . . . .
N1 N 0.2389(4) 0.7936(2) 0.4647(2) 0.0126(5) Uani 1 1 d . . . . .
C1 C 0.2814(4) 0.2235(3) 0.2741(2) 0.0133(6) Uani 1 1 d . . . . .
C2 C 0.2939(5) 0.1391(3) 0.2009(3) 0.0179(7) Uani 1 1 d . . . . .
H2 H 0.289848 0.065107 0.212152 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3124(5) 0.1629(3) 0.1115(3) 0.0220(7) Uani 1 1 d . . . . .
H3 H 0.321456 0.105045 0.061522 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3180(5) 0.2705(3) 0.0939(2) 0.0215(7) Uani 1 1 d . . . . .
H4 H 0.330561 0.286053 0.032227 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3052(5) 0.3545(3) 0.1661(2) 0.0178(6) Uani 1 1 d . . . . .
H5 H 0.308309 0.428032 0.153758 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2876(4) 0.3330(3) 0.2581(2) 0.0130(6) Uani 1 1 d . . . . .
C7 C 0.2754(5) 0.4227(3) 0.3312(2) 0.0156(6) Uani 1 1 d . . . . .
C8 C 0.2639(5) 0.5013(3) 0.3880(2) 0.0154(6) Uani 1 1 d . . . . .
C9 C 0.2485(5) 0.6012(3) 0.4495(2) 0.0143(6) Uani 1 1 d . . . . .
C10 C 0.2482(4) 0.6977(3) 0.4104(2) 0.0137(6) Uani 1 1 d . . . . .
H10 H 0.254601 0.695376 0.344304 0.016 Uiso 1 1 calc R U . . .
C11 C 0.2365(5) 0.6060(3) 0.5462(3) 0.0166(6) Uani 1 1 d . . . . .
H11 H 0.236179 0.540845 0.574235 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2277(4) 0.8009(3) 0.5581(2) 0.0138(6) Uani 1 1 d . . . . .
H12 H 0.221322 0.870481 0.594967 0.017 Uiso 1 1 calc R U . . .
C13 C 0.2252(4) 0.7067(3) 0.6013(2) 0.0147(6) Uani 1 1 d . . . . .
C14 C 0.2132(5) 0.7165(3) 0.7007(2) 0.0162(6) Uani 1 1 d . . . . .
C15 C 0.2046(5) 0.7182(3) 0.7832(3) 0.0165(6) Uani 1 1 d . . . . .
C16 C 0.1961(5) 0.7208(3) 0.8827(2) 0.0169(6) Uani 1 1 d . . . . .
C17 C 0.1955(5) 0.6243(3) 0.9230(3) 0.0208(7) Uani 1 1 d . . . . .
C18 C 0.1865(6) 0.6295(4) 1.0201(3) 0.0301(9) Uani 1 1 d . . . . .
H18 H 0.187980 0.564281 1.048024 0.036 Uiso 1 1 calc R U . . .
C19 C 0.1756(6) 0.7287(4) 1.0760(3) 0.0337(10) Uani 1 1 d . . . . .
H19 H 0.166821 0.731153 1.141769 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1773(6) 0.8248(4) 1.0367(3) 0.0302(9) Uani 1 1 d . . . . .
H20 H 0.171554 0.893139 1.075715 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1874(5) 0.8212(3) 0.9409(3) 0.0217(7) Uani 1 1 d . . . . .
H21 H 0.188518 0.887191 0.914170 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2492(5) 0.8963(3) 0.4228(3) 0.0173(6) Uani 1 1 d . . . . .
H22A H 0.172370 0.948093 0.451232 0.026 Uiso 1 1 calc R U . . .
H22B H 0.197681 0.878906 0.351800 0.026 Uiso 1 1 calc R U . . .
H22C H 0.384513 0.929697 0.437574 0.026 Uiso 1 1 calc R U . . .
S1 S 0.28790(13) 0.17282(7) 0.68893(6) 0.01875(17) Uani 1 1 d . . . . .
F1 F 0.3169(4) 0.1633(3) 0.87355(17) 0.0443(7) Uani 1 1 d . . . . .
F2 F 0.0855(4) 0.0505(2) 0.77565(19) 0.0392(6) Uani 1 1 d . . . . .
F3 F 0.3794(4) 0.0178(2) 0.7918(2) 0.0490(7) Uani 1 1 d . . . . .
O1 O 0.1503(4) 0.2503(2) 0.6933(2) 0.0304(6) Uani 1 1 d . . . . .
O2 O 0.4873(4) 0.2191(3) 0.7153(2) 0.0325(7) Uani 1 1 d . . . . .
O3 O 0.2341(5) 0.0868(2) 0.6039(2) 0.0316(6) Uani 1 1 d . . . . .
C23 C 0.2659(6) 0.0973(3) 0.7873(3) 0.0237(7) 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
I1 C1 2.094(3) . ?
I2 C17 2.096(4) . ?
N1 C10 1.332(4) . ?
N1 C12 1.344(4) . ?
N1 C22 1.484(4) . ?
C1 C2 1.388(5) . ?
C1 C6 1.402(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(5) . ?
C6 C7 1.428(5) . ?
C7 C8 1.192(5) . ?
C8 C9 1.432(5) . ?
C9 C10 1.389(4) . ?
C9 C11 1.395(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C13 1.389(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(4) . ?
C13 C14 1.429(5) . ?
C14 C15 1.189(5) . ?
C15 C16 1.431(5) . ?
C16 C17 1.398(5) . ?
C16 C21 1.402(5) . ?
C17 C18 1.395(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S1 O1 1.434(3) . ?
S1 O2 1.431(3) . ?
S1 O3 1.445(3) . ?
S1 C23 1.824(4) . ?
F1 C23 1.328(5) . ?
F2 C23 1.328(5) . ?
F3 C23 1.325(5) . ?

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
C10 N1 C12 121.9(3) . . ?
C10 N1 C22 119.5(3) . . ?
C12 N1 C22 118.6(3) . . ?
C2 C1 I1 119.2(2) . . ?
C2 C1 C6 120.5(3) . . ?
C6 C1 I1 120.3(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 C7 122.6(3) . . ?
C5 C6 C7 119.0(3) . . ?
C8 C7 C6 176.2(3) . . ?
C7 C8 C9 175.0(3) . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 C11 118.9(3) . . ?
C11 C9 C8 123.2(3) . . ?
N1 C10 C9 120.5(3) . . ?
N1 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C9 C11 H11 120.2 . . ?
C13 C11 C9 119.5(3) . . ?
C13 C11 H11 120.2 . . ?
N1 C12 H12 119.9 . . ?
N1 C12 C13 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C13 C12 118.8(3) . . ?
C11 C13 C14 121.9(3) . . ?
C12 C13 C14 119.3(3) . . ?
C15 C14 C13 176.2(4) . . ?
C14 C15 C16 179.5(4) . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 C21 119.3(3) . . ?
C21 C16 C15 119.8(3) . . ?
C16 C17 I2 120.8(3) . . ?
C18 C17 I2 119.7(3) . . ?
C18 C17 C16 119.5(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.5(4) . . ?
C20 C21 H21 119.8 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 S1 O3 114.44(18) . . ?
O1 S1 C23 103.13(18) . . ?
O2 S1 O1 115.67(19) . . ?
O2 S1 O3 115.09(19) . . ?
O2 S1 C23 103.58(18) . . ?
O3 S1 C23 102.37(18) . . ?
F1 C23 S1 111.2(3) . . ?
F1 C23 F2 107.8(3) . . ?
F2 C23 S1 111.7(3) . . ?
F3 C23 S1 111.6(3) . . ?
F3 C23 F1 107.0(3) . . ?
F3 C23 F2 107.3(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
I1 C1 C2 C3 -179.3(3) . . . . ?
I1 C1 C6 C5 179.7(2) . . . . ?
I1 C1 C6 C7 -0.7(4) . . . . ?
I2 C17 C18 C19 -178.4(3) . . . . ?
N1 C12 C13 C11 0.6(5) . . . . ?
N1 C12 C13 C14 180.0(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C2 C1 C6 C7 -179.9(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C4 C5 C6 C7 179.8(3) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C8 C9 C10 N1 -178.3(3) . . . . ?
C8 C9 C11 C13 178.9(3) . . . . ?
C9 C11 C13 C12 -0.5(5) . . . . ?
C9 C11 C13 C14 -179.9(3) . . . . ?
C10 N1 C12 C13 0.0(5) . . . . ?
C10 C9 C11 C13 -0.2(5) . . . . ?
C11 C9 C10 N1 0.8(5) . . . . ?
C12 N1 C10 C9 -0.7(5) . . . . ?
C15 C16 C17 I2 -0.5(4) . . . . ?
C15 C16 C17 C18 -179.8(3) . . . . ?
C15 C16 C21 C20 179.4(3) . . . . ?
C16 C17 C18 C19 0.9(6) . . . . ?
C17 C16 C21 C20 -0.4(5) . . . . ?
C17 C18 C19 C20 -1.3(6) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
C19 C20 C21 C16 0.0(6) . . . . ?
C21 C16 C17 I2 179.3(3) . . . . ?
C21 C16 C17 C18 -0.1(5) . . . . ?
C22 N1 C10 C9 176.8(3) . . . . ?
C22 N1 C12 C13 -177.5(3) . . . . ?
O1 S1 C23 F1 -63.1(3) . . . . ?
O1 S1 C23 F2 57.5(3) . . . . ?
O1 S1 C23 F3 177.6(3) . . . . ?
O2 S1 C23 F1 57.9(3) . . . . ?
O2 S1 C23 F2 178.4(3) . . . . ?
O2 S1 C23 F3 -61.5(3) . . . . ?
O3 S1 C23 F1 177.9(3) . . . . ?
O3 S1 C23 F2 -61.6(3) . . . . ?
O3 S1 C23 F3 58.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umt_ob216
_database_code_depnum_ccdc_archive 'CCDC 2075102'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2021-04-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 I2 N2, C F3 O3 S'
_chemical_formula_sum            'C23 H15 F3 I2 N2 O3 S'
_chemical_formula_weight         710.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   22.544(3)
_cell_length_b                   22.544(3)
_cell_length_c                   9.5927(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4875.1(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9052
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.395
_cell_measurement_theta_min      2.555
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    2.717
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0856 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.8421.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            142896
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              fine-focus
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4439
_reflns_number_total             4993
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 
;
 Flack x determined using 1852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.058(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0216P)²+4.8266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2A
 0.87 with sigma of 0.02
 S1-O3 \\sim S1-O3'
 with sigma of 0.02
 F1-F2 \\sim F1'-F2'
 with sigma of 0.04
 S1-O2 \\sim S1-O2'
 with sigma of 0.02
 S1-C23 \\sim S1-C23'
 with sigma of 0.02
 F1-C23 \\sim F1'-C23'
 with sigma of 0.02
 S1-F2 \\sim S1-F2'
 with sigma of 0.04
 F2-F3 \\sim F2'-F3'
 with sigma of 0.04
 F2-C23 \\sim F2'-C23'
 with sigma of 0.02
 S1-F3 \\sim S1-F3'
 with sigma of 0.04
 F1-F3 \\sim F1'-F3'
 with sigma of 0.04
 F3-C23 \\sim F3'-C23'
 with sigma of 0.02
 S1-F1 \\sim S1-F1'
 with sigma of 0.04
3. Others
 Sof(F1')=Sof(F2')=Sof(F3')=Sof(O2')=Sof(O3')=Sof(C23')=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(O2)=Sof(O3)=Sof(C23)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C18(H18), C19(H19),
 C20(H20), C21(H21)
4.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.77013(2) 0.55677(2) 0.37383(4) 0.02085(9) Uani 1 1 d . . . . .
I2 I 0.66847(2) 0.90275(2) 1.05281(4) 0.02757(10) Uani 1 1 d . . . . .
N1 N 0.8692(2) 0.8403(2) 0.6456(5) 0.0227(11) Uani 1 1 d . . . . .
N2 N 0.7603(2) 0.6958(2) 0.5968(5) 0.0217(11) Uani 1 1 d D . . . .
H2A H 0.769(3) 0.6668(19) 0.536(5) 0.023(15) Uiso 1 1 d D . . . .
H2B H 0.728(3) 0.690(3) 0.650(6) 0.024(17) Uiso 1 1 d . . . . .
C1 C 0.8463(2) 0.5657(2) 0.2496(6) 0.0187(12) Uani 1 1 d . . . . .
C2 C 0.8601(2) 0.5204(3) 0.1575(6) 0.0208(13) Uani 1 1 d . . . . .
H2 H 0.835166 0.486566 0.150674 0.025 Uiso 1 1 calc R U . . .
C3 C 0.9107(3) 0.5248(2) 0.0750(6) 0.0255(13) Uani 1 1 d . . . . .
H3 H 0.920376 0.493900 0.011566 0.031 Uiso 1 1 calc R U . . .
C4 C 0.9468(3) 0.5742(3) 0.0854(6) 0.0229(13) Uani 1 1 d . . . . .
H4 H 0.981422 0.577101 0.029255 0.027 Uiso 1 1 calc R U . . .
C5 C 0.9329(2) 0.6191(3) 0.1768(6) 0.0203(12) Uani 1 1 d . . . . .
H5 H 0.958160 0.652711 0.183150 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8823(2) 0.6161(2) 0.2605(6) 0.0190(12) Uani 1 1 d . . . . .
C7 C 0.8697(2) 0.6635(2) 0.3548(6) 0.0187(12) Uani 1 1 d . . . . .
C8 C 0.8617(2) 0.7049(2) 0.4323(6) 0.0200(12) Uani 1 1 d . . . . .
C9 C 0.8475(2) 0.7494(2) 0.5309(6) 0.0187(12) Uani 1 1 d . . . . .
C10 C 0.7950(2) 0.7425(2) 0.6132(6) 0.0192(12) Uani 1 1 d . . . . .
C11 C 0.8821(2) 0.7986(2) 0.5492(7) 0.0224(12) Uani 1 1 d . . . . .
H11 H 0.916297 0.803619 0.492401 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8206(2) 0.8348(3) 0.7253(6) 0.0237(13) Uani 1 1 d . . . . .
H12 H 0.812522 0.864604 0.792778 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7820(2) 0.7876(2) 0.7130(6) 0.0199(12) Uani 1 1 d . . . . .
C14 C 0.7301(3) 0.7851(2) 0.7945(6) 0.0220(12) Uani 1 1 d . . . . .
C15 C 0.6851(2) 0.7836(2) 0.8612(6) 0.0191(12) Uani 1 1 d . . . . .
C16 C 0.6329(2) 0.7804(2) 0.9459(6) 0.0191(11) Uani 1 1 d . . . . .
C17 C 0.6184(2) 0.8241(2) 1.0435(6) 0.0210(12) Uani 1 1 d . . . . .
C18 C 0.5709(2) 0.8177(3) 1.1315(6) 0.0248(13) Uani 1 1 d . . . . .
H18 H 0.561739 0.847754 1.197410 0.030 Uiso 1 1 calc R U . . .
C19 C 0.5364(2) 0.7666(3) 1.1232(7) 0.0284(13) Uani 1 1 d . . . . .
H19 H 0.504014 0.761195 1.185358 0.034 Uiso 1 1 calc R U . . .
C20 C 0.5491(2) 0.7240(3) 1.0245(7) 0.0260(14) Uani 1 1 d . . . . .
H20 H 0.524704 0.689775 1.017329 0.031 Uiso 1 1 calc R U . . .
C21 C 0.5966(2) 0.7303(2) 0.9366(6) 0.0231(12) Uani 1 1 d . . . . .
H21 H 0.604913 0.700564 0.869233 0.028 Uiso 1 1 calc R U . . .
C22 C 0.9099(3) 0.8910(2) 0.6675(8) 0.0330(16) Uani 1 1 d . . . . .
H22A H 0.938374 0.881117 0.741216 0.050 Uiso 1 1 calc R U . . .
H22B H 0.887025 0.926001 0.694922 0.050 Uiso 1 1 calc R U . . .
H22C H 0.931384 0.899297 0.580790 0.050 Uiso 1 1 calc R U . . .
S1 S 0.64474(7) 0.57767(7) 0.6906(2) 0.0305(4) Uani 1 1 d D . . . .
O1 O 0.6680(2) 0.63399(19) 0.7327(5) 0.0377(11) Uani 1 1 d . . . . .
F1 F 0.5435(3) 0.6327(4) 0.6976(11) 0.056(3) Uani 0.680(10) 1 d D . P A 1
F2 F 0.5425(5) 0.5541(5) 0.5805(11) 0.080(3) Uani 0.680(10) 1 d D . P A 1
F3 F 0.5868(4) 0.6293(5) 0.5021(8) 0.102(4) Uani 0.680(10) 1 d D . P A 1
O2 O 0.6762(4) 0.5444(4) 0.5939(13) 0.070(4) Uani 0.680(10) 1 d D . P A 1
O3 O 0.6265(4) 0.5426(3) 0.8161(9) 0.047(2) Uani 0.680(10) 1 d D . P A 1
C23 C 0.5760(5) 0.5977(6) 0.6169(14) 0.043(3) Uani 0.680(10) 1 d D . P A 1
F1' F 0.5509(5) 0.5924(7) 0.8293(13) 0.058(5) Uani 0.320(10) 1 d D . P A 2
F2' F 0.5418(10) 0.5299(11) 0.663(3) 0.094(9) Uani 0.320(10) 1 d D . P A 2
F3' F 0.5441(11) 0.6209(13) 0.621(2) 0.108(12) Uani 0.320(10) 1 d D . P A 2
O2' O 0.6550(6) 0.5688(7) 0.5340(14) 0.028(4) Uani 0.320(10) 1 d D . P A 2
O3' O 0.6624(9) 0.5316(7) 0.7690(19) 0.046(5) Uani 0.320(10) 1 d D . P A 2
C23' C 0.5658(8) 0.5787(12) 0.701(3) 0.058(8) Uani 0.320(10) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.100(5) . ?
I2 C17 2.104(5) . ?
N1 C11 1.349(7) . ?
N1 C12 1.341(7) . ?
N1 C22 1.481(7) . ?
N2 H2A 0.90(3) . ?
N2 H2B 0.90(6) . ?
N2 C10 1.322(7) . ?
C1 C2 1.386(8) . ?
C1 C6 1.399(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(8) . ?
C6 C7 1.429(8) . ?
C7 C8 1.207(8) . ?
C8 C9 1.415(8) . ?
C9 C10 1.431(8) . ?
C9 C11 1.369(7) . ?
C10 C13 1.427(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.380(8) . ?
C13 C14 1.409(8) . ?
C14 C15 1.200(8) . ?
C15 C16 1.432(8) . ?
C16 C17 1.399(8) . ?
C16 C21 1.397(8) . ?
C17 C18 1.370(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(9) . ?
C20 H20 0.9500 . ?
C20 C21 1.370(8) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S1 O1 1.432(4) . ?
S1 O2 1.388(7) . ?
S1 O3 1.498(8) . ?
S1 C23 1.763(12) . ?
S1 O2' 1.534(13) . ?
S1 O3' 1.343(13) . ?
S1 C23' 1.783(19) . ?
F1 C23 1.325(15) . ?
F2 C23 1.288(13) . ?
F3 C23 1.335(16) . ?
F1' C23' 1.31(2) . ?
F2' C23' 1.28(2) . ?
F3' C23' 1.32(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
C11 N1 C22 120.0(5) . . ?
C12 N1 C11 120.2(5) . . ?
C12 N1 C22 119.7(5) . . ?
H2A N2 H2B 117(5) . . ?
C10 N2 H2A 122(4) . . ?
C10 N2 H2B 122(4) . . ?
C2 C1 I1 118.3(4) . . ?
C2 C1 C6 121.0(5) . . ?
C6 C1 I1 120.6(4) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(5) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 122.6(5) . . ?
C5 C6 C1 118.0(5) . . ?
C5 C6 C7 119.3(5) . . ?
C8 C7 C6 176.6(6) . . ?
C7 C8 C9 173.4(6) . . ?
C8 C9 C10 118.7(5) . . ?
C11 C9 C8 122.0(5) . . ?
C11 C9 C10 119.3(5) . . ?
N2 C10 C9 120.7(5) . . ?
N2 C10 C13 121.8(5) . . ?
C13 C10 C9 117.6(5) . . ?
N1 C11 C9 121.9(5) . . ?
N1 C11 H11 119.0 . . ?
C9 C11 H11 119.0 . . ?
N1 C12 H12 118.8 . . ?
N1 C12 C13 122.4(5) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C10 118.6(5) . . ?
C12 C13 C14 120.5(5) . . ?
C14 C13 C10 120.9(5) . . ?
C15 C14 C13 178.3(6) . . ?
C14 C15 C16 177.2(6) . . ?
C17 C16 C15 122.4(5) . . ?
C21 C16 C15 119.1(5) . . ?
C21 C16 C17 118.3(5) . . ?
C16 C17 I2 119.8(4) . . ?
C18 C17 I2 118.8(4) . . ?
C18 C17 C16 121.4(5) . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.3(6) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(6) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(6) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.2(5) . . ?
C20 C21 H21 119.9 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 S1 O3 110.1(4) . . ?
O1 S1 C23 102.0(4) . . ?
O1 S1 O2' 109.6(7) . . ?
O1 S1 C23' 109.8(8) . . ?
O2 S1 O1 118.7(4) . . ?
O2 S1 O3 113.1(6) . . ?
O2 S1 C23 108.6(7) . . ?
O3 S1 C23 102.5(6) . . ?
O2' S1 C23' 102.0(9) . . ?
O3' S1 O1 114.8(8) . . ?
O3' S1 O2' 113.8(9) . . ?
O3' S1 C23' 105.9(12) . . ?
F1 C23 S1 113.8(9) . . ?
F1 C23 F3 105.3(11) . . ?
F2 C23 S1 115.4(10) . . ?
F2 C23 F1 106.9(11) . . ?
F2 C23 F3 107.0(11) . . ?
F3 C23 S1 107.9(9) . . ?
F1' C23' S1 108.2(14) . . ?
F1' C23' F3' 106(2) . . ?
F2' C23' S1 113.3(18) . . ?
F2' C23' F1' 111(2) . . ?
F2' C23' F3' 107(2) . . ?
F3' C23' S1 110.2(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2B O1 0.90(6) 2.01(6) 2.822(6) 149(5) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 C3 -179.2(4) . . . . ?
I1 C1 C6 C5 179.0(4) . . . . ?
I1 C1 C6 C7 -0.1(7) . . . . ?
I2 C17 C18 C19 178.0(4) . . . . ?
N1 C12 C13 C10 1.1(8) . . . . ?
N1 C12 C13 C14 -177.1(5) . . . . ?
N2 C10 C13 C12 179.3(5) . . . . ?
N2 C10 C13 C14 -2.5(8) . . . . ?
C1 C2 C3 C4 0.0(9) . . . . ?
C2 C1 C6 C5 -0.6(8) . . . . ?
C2 C1 C6 C7 -179.6(5) . . . . ?
C2 C3 C4 C5 -0.2(9) . . . . ?
C3 C4 C5 C6 -0.1(8) . . . . ?
C4 C5 C6 C1 0.5(8) . . . . ?
C4 C5 C6 C7 179.6(5) . . . . ?
C6 C1 C2 C3 0.4(8) . . . . ?
C8 C9 C10 N2 -0.5(8) . . . . ?
C8 C9 C10 C13 179.2(5) . . . . ?
C8 C9 C11 N1 -178.4(5) . . . . ?
C9 C10 C13 C12 -0.4(8) . . . . ?
C9 C10 C13 C14 177.8(5) . . . . ?
C10 C9 C11 N1 1.9(8) . . . . ?
C11 N1 C12 C13 -0.3(8) . . . . ?
C11 C9 C10 N2 179.3(5) . . . . ?
C11 C9 C10 C13 -1.0(8) . . . . ?
C12 N1 C11 C9 -1.3(8) . . . . ?
C15 C16 C17 I2 7.3(7) . . . . ?
C15 C16 C17 C18 -174.5(5) . . . . ?
C15 C16 C21 C20 174.8(5) . . . . ?
C16 C17 C18 C19 -0.3(8) . . . . ?
C17 C16 C21 C20 -1.9(8) . . . . ?
C17 C18 C19 C20 -1.7(9) . . . . ?
C18 C19 C20 C21 1.9(9) . . . . ?
C19 C20 C21 C16 0.0(9) . . . . ?
C21 C16 C17 I2 -176.2(4) . . . . ?
C21 C16 C17 C18 2.1(8) . . . . ?
C22 N1 C11 C9 176.3(5) . . . . ?
C22 N1 C12 C13 -177.9(5) . . . . ?
O1 S1 C23 F1 -50.1(10) . . . . ?
O1 S1 C23 F2 -174.1(10) . . . . ?
O1 S1 C23 F3 66.4(9) . . . . ?
O1 S1 C23' F1' -57(2) . . . . ?
O1 S1 C23' F2' 178.9(19) . . . . ?
O1 S1 C23' F3' 59(2) . . . . ?
O2 S1 C23 F1 -176.2(10) . . . . ?
O2 S1 C23 F2 59.7(12) . . . . ?
O2 S1 C23 F3 -59.7(10) . . . . ?
O3 S1 C23 F1 63.9(10) . . . . ?
O3 S1 C23 F2 -60.2(11) . . . . ?
O3 S1 C23 F3 -179.6(9) . . . . ?
O2' S1 C23' F1' -173.3(17) . . . . ?
O2' S1 C23' F2' 63(2) . . . . ?
O2' S1 C23' F3' -57(2) . . . . ?
O3' S1 C23' F1' 67(2) . . . . ?
O3' S1 C23' F2' -57(2) . . . . ?
O3' S1 C23' F3' -177(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
