# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ob145
_database_code_depnum_ccdc_archive 'CCDC 2036128'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2020-10-08 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_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 F I2 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H15 F7 I2 N2 O6 S2'
_chemical_formula_weight         878.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   22.3717(18)
_cell_length_b                   12.7201(10)
_cell_length_c                   10.8086(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3075.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9473
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.089
_cell_measurement_theta_min      3.071
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.742
_exptl_absorpt_coefficient_mu    2.263
_exptl_absorpt_correction_T_max  0.6022
_exptl_absorpt_correction_T_min  0.5246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0717 before and 0.0619 after correction. The Ratio of minimum to maximum transmission is 0.8711. 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    1.897
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            46254
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.105
_diffrn_reflns_theta_max         25.105
_diffrn_reflns_theta_min         2.635
_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 0.997
_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_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                2199
_reflns_number_total             2735
_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         1.137
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.125
_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)+(0.0455P)²+11.1749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0994
_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. Rigid body (RIGU) restrains
 C2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C9(H9), C10(H10)
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 0.33683(2) 0.61508(2) 0.36697(3) 0.02475(14) Uani 1 1 d . . . . .
F1 F 0.500000 0.7618(4) 0.750000 0.0526(14) Uani 1 2 d S T P . .
N1 N 0.27901(18) 0.3246(3) 0.2112(4) 0.0200(9) Uani 1 1 d . . . . .
C1 C 0.2879(2) 0.4269(4) 0.2395(5) 0.0199(11) Uani 1 1 d . . . . .
H1 H 0.266711 0.479636 0.195284 0.024 Uiso 1 1 calc R . . . .
C2 C 0.3268(2) 0.4557(4) 0.3306(5) 0.0205(11) Uani 1 1 d . U . . .
C3 C 0.3586(2) 0.3775(4) 0.3965(5) 0.0212(11) Uani 1 1 d . U . . .
C4 C 0.3487(2) 0.2734(4) 0.3629(5) 0.0228(11) Uani 1 1 d . U . . .
H4 H 0.369516 0.218632 0.404394 0.027 Uiso 1 1 calc R . . . .
C5 C 0.3088(2) 0.2490(4) 0.2696(5) 0.0236(11) Uani 1 1 d . . . . .
H5 H 0.302668 0.177652 0.247060 0.028 Uiso 1 1 calc R . . . .
C6 C 0.3971(2) 0.4070(4) 0.4945(5) 0.0239(12) Uani 1 1 d . . . . .
C7 C 0.4288(2) 0.4412(4) 0.5745(5) 0.0241(11) Uani 1 1 d . . . . .
C8 C 0.4652(2) 0.4947(4) 0.6650(5) 0.0230(11) Uani 1 1 d . . . . .
C9 C 0.500000 0.4401(6) 0.750000 0.0228(16) Uani 1 2 d S T P . .
H9 H 0.500000 0.365373 0.750001 0.027 Uiso 1 2 calc RS T P . .
C10 C 0.4653(2) 0.6042(4) 0.6648(5) 0.0280(12) Uani 1 1 d . . . . .
H10 H 0.441790 0.642286 0.606835 0.034 Uiso 1 1 calc R . . . .
C11 C 0.500000 0.6561(6) 0.750000 0.0328(18) Uani 1 2 d S T P . .
C12 C 0.2320(3) 0.2981(4) 0.1193(5) 0.0277(12) Uani 1 1 d . . . . .
H12A H 0.193198 0.293923 0.160949 0.042 Uiso 1 1 calc GR . . . .
H12B H 0.241285 0.230183 0.081018 0.042 Uiso 1 1 calc GR . . . .
H12C H 0.230645 0.352680 0.055435 0.042 Uiso 1 1 calc GR . . . .
S1 S 0.32891(6) 0.93776(10) 0.45377(12) 0.0226(3) Uani 1 1 d . . . . .
F2 F 0.4137(2) 0.8707(5) 0.5950(5) 0.0987(19) Uani 1 1 d . . . . .
F3 F 0.44357(19) 0.9508(5) 0.4341(6) 0.1001(19) Uani 1 1 d . . . . .
F4 F 0.4067(2) 1.0389(5) 0.5844(6) 0.1001(19) Uani 1 1 d . . . . .
O1 O 0.3304(2) 0.8413(3) 0.3865(4) 0.0442(11) Uani 1 1 d . . . . .
O2 O 0.2898(2) 0.9349(3) 0.5597(4) 0.0391(10) Uani 1 1 d . . . . .
O3 O 0.32205(18) 1.0310(3) 0.3798(4) 0.0345(10) Uani 1 1 d . . . . .
C13 C 0.4027(3) 0.9500(6) 0.5201(8) 0.059(2) 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 C2 2.077(5) . ?
F1 C11 1.345(9) . ?
N1 C1 1.353(6) . ?
N1 C5 1.330(6) . ?
N1 C12 1.484(6) . ?
C1 C2 1.364(7) . ?
C2 C3 1.416(7) . ?
C3 C4 1.391(7) . ?
C3 C6 1.416(7) . ?
C4 C5 1.381(7) . ?
C6 C7 1.199(7) . ?
C7 C8 1.443(7) . ?
C8 C9 1.391(6) . ?
C8 C10 1.394(8) . ?
C10 C11 1.374(7) . ?
S1 O1 1.427(4) . ?
S1 O2 1.441(4) . ?
S1 O3 1.439(4) . ?
S1 C13 1.807(7) . ?
F2 C13 1.316(9) . ?
F3 C13 1.303(10) . ?
F4 C13 1.332(9) . ?

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 C12 118.3(4) . . ?
C5 N1 C1 121.0(4) . . ?
C5 N1 C12 120.6(4) . . ?
N1 C1 C2 121.0(5) . . ?
C1 C2 I1 117.9(4) . . ?
C1 C2 C3 119.7(5) . . ?
C3 C2 I1 122.4(4) . . ?
C4 C3 C2 117.2(5) . . ?
C4 C3 C6 123.0(5) . . ?
C6 C3 C2 119.7(5) . . ?
C5 C4 C3 120.5(5) . . ?
N1 C5 C4 120.6(5) . . ?
C7 C6 C3 174.1(6) . . ?
C6 C7 C8 173.2(6) . . ?
C9 C8 C7 121.9(5) . . ?
C9 C8 C10 120.0(5) . . ?
C10 C8 C7 118.1(5) . . ?
C8 C9 C8 120.1(7) . 3_656 ?
C11 C10 C8 118.7(5) . . ?
F1 C11 C10 118.7(4) . . ?
F1 C11 C10 118.7(4) . 3_656 ?
C10 C11 C10 122.6(8) . 3_656 ?
O1 S1 O2 113.4(3) . . ?
O1 S1 O3 115.4(3) . . ?
O1 S1 C13 104.7(3) . . ?
O2 S1 C13 104.0(4) . . ?
O3 S1 O2 113.4(2) . . ?
O3 S1 C13 104.3(3) . . ?
F2 C13 S1 110.4(6) . . ?
F2 C13 F4 108.5(7) . . ?
F3 C13 S1 111.0(6) . . ?
F3 C13 F2 108.3(7) . . ?
F3 C13 F4 108.6(7) . . ?
F4 C13 S1 110.0(5) . . ?

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

data_umt_ob146
_database_code_depnum_ccdc_archive 'CCDC 2036129'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2020-10-08 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_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 F I2 N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H15 F7 I2 N2 O6 S2'
_chemical_formula_weight         878.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.8488(4)
_cell_length_b                   10.3020(6)
_cell_length_c                   18.2739(10)
_cell_angle_alpha                80.787(2)
_cell_angle_beta                 85.112(2)
_cell_angle_gamma                86.769(2)
_cell_volume                     1451.86(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.406
_cell_measurement_theta_min      2.761
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.646
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  0.6028
_exptl_absorpt_correction_T_min  0.5372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0664 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.8912. 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    2.009
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            56291
_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         26.421
_diffrn_reflns_theta_min         2.607
_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                4984
_reflns_number_total             5956
_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         1.116
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5956
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.069
_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)+(0.0309P)²+2.6925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0685
_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:
 C1(H1), C2(H2), C3(H3), C9(H9), C11(H11), C12(H12), C17(H17), C18(H18),
 C20(H20)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), 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 0.01156(3) 0.76762(2) 0.80163(2) 0.01974(7) Uani 1 1 d . . . . .
I2 I 0.53503(3) 0.47866(2) 0.18976(2) 0.02062(7) Uani 1 1 d . . . . .
F1 F 0.4135(3) 0.8980(2) 0.47003(12) 0.0289(5) Uani 1 1 d . . . . .
N1 N -0.1548(3) 0.3971(3) 0.91975(15) 0.0146(6) Uani 1 1 d . . . . .
N2 N 0.4083(4) 0.0749(3) 0.23923(16) 0.0173(6) Uani 1 1 d . . . . .
C1 C -0.1279(4) 0.3119(3) 0.8711(2) 0.0189(7) Uani 1 1 d . . . . .
H1 H -0.156118 0.222596 0.886369 0.023 Uiso 1 1 calc R . . . .
C2 C -0.0603(4) 0.3516(3) 0.7997(2) 0.0190(7) Uani 1 1 d . . . . .
H2 H -0.042287 0.290352 0.765777 0.023 Uiso 1 1 calc R . . . .
C3 C -0.1164(4) 0.5238(3) 0.90014(19) 0.0151(7) Uani 1 1 d . . . . .
H3 H -0.137125 0.582363 0.935473 0.018 Uiso 1 1 calc R . . . .
C4 C -0.0473(4) 0.5705(3) 0.82958(19) 0.0152(7) Uani 1 1 d . . . . .
C5 C -0.0179(4) 0.4834(3) 0.77727(19) 0.0173(7) Uani 1 1 d . . . . .
C6 C 0.0538(4) 0.5279(4) 0.7034(2) 0.0194(7) Uani 1 1 d . . . . .
C7 C 0.1176(4) 0.5687(4) 0.6431(2) 0.0196(7) Uani 1 1 d . . . . .
C8 C 0.2032(4) 0.6134(3) 0.57158(19) 0.0169(7) Uani 1 1 d . . . . .
C9 C 0.2637(4) 0.7407(3) 0.55434(19) 0.0185(7) Uani 1 1 d . . . . .
H9 H 0.242486 0.801913 0.588143 0.022 Uiso 1 1 calc R . . . .
C10 C 0.3552(4) 0.7746(3) 0.4866(2) 0.0194(7) Uani 1 1 d . . . . .
C11 C 0.3898(4) 0.6901(3) 0.43520(19) 0.0184(7) Uani 1 1 d . . . . .
H11 H 0.455428 0.716651 0.389667 0.022 Uiso 1 1 calc R . . . .
C12 C 0.2319(4) 0.5261(3) 0.52021(19) 0.0172(7) Uani 1 1 d . . . . .
H12 H 0.187984 0.440552 0.531481 0.021 Uiso 1 1 calc R . . . .
C13 C 0.3251(4) 0.5644(3) 0.45232(19) 0.0167(7) Uani 1 1 d . . . . .
C14 C 0.3532(4) 0.4699(3) 0.40189(19) 0.0175(7) Uani 1 1 d . . . . .
C15 C 0.3718(4) 0.3859(3) 0.36293(19) 0.0179(7) Uani 1 1 d . . . . .
C16 C 0.3887(4) 0.2806(3) 0.32040(19) 0.0162(7) Uani 1 1 d . . . . .
C17 C 0.3345(4) 0.1555(3) 0.3522(2) 0.0198(7) Uani 1 1 d . . . . .
H17 H 0.289511 0.140374 0.402586 0.024 Uiso 1 1 calc R . . . .
C18 C 0.3457(5) 0.0551(4) 0.31116(19) 0.0201(7) Uani 1 1 d . . . . .
H18 H 0.309214 -0.029497 0.333457 0.024 Uiso 1 1 calc R . . . .
C19 C 0.4565(4) 0.2973(3) 0.24583(19) 0.0154(7) Uani 1 1 d . . . . .
C20 C 0.4641(4) 0.1924(3) 0.20725(19) 0.0166(7) Uani 1 1 d . . . . .
H20 H 0.510042 0.203791 0.156943 0.020 Uiso 1 1 calc R . . . .
C21 C -0.2197(5) 0.3496(4) 0.99764(19) 0.0211(8) Uani 1 1 d . . . . .
H21A H -0.126760 0.302316 1.024843 0.032 Uiso 1 1 calc GR . . . .
H21B H -0.313024 0.290221 0.997773 0.032 Uiso 1 1 calc GR . . . .
H21C H -0.262093 0.424847 1.021703 0.032 Uiso 1 1 calc GR . . . .
C22 C 0.4168(5) -0.0355(4) 0.1958(2) 0.0241(8) Uani 1 1 d . . . . .
H22A H 0.439198 -0.001352 0.142807 0.036 Uiso 1 1 calc GR . . . .
H22B H 0.307706 -0.079396 0.203698 0.036 Uiso 1 1 calc GR . . . .
H22C H 0.509230 -0.098715 0.212093 0.036 Uiso 1 1 calc GR . . . .
S1 S 0.17181(12) 1.08223(9) 0.68729(5) 0.02052(19) Uani 1 1 d . . . . .
F2 F -0.0085(3) 1.0444(2) 0.57841(13) 0.0371(6) Uani 1 1 d . . . . .
F3 F -0.0046(3) 1.2471(2) 0.59603(16) 0.0436(7) Uani 1 1 d . . . . .
F4 F 0.2157(3) 1.1573(3) 0.54285(13) 0.0439(7) Uani 1 1 d . . . . .
O1 O 0.0165(3) 1.0674(3) 0.73592(15) 0.0290(6) Uani 1 1 d . . . . .
O2 O 0.2660(4) 0.9603(3) 0.67869(16) 0.0324(7) Uani 1 1 d . . . . .
O3 O 0.2739(4) 1.1895(3) 0.69612(16) 0.0325(7) Uani 1 1 d . . . . .
C23 C 0.0907(5) 1.1354(4) 0.5964(2) 0.0272(9) Uani 1 1 d . . . . .
S2 S 0.66040(10) 0.75328(8) 0.03375(5) 0.01427(17) Uani 1 1 d . . . . .
F5 F 0.9153(3) 0.9002(3) -0.01703(15) 0.0469(7) Uani 1 1 d . . . . .
F6 F 0.6833(3) 1.0101(2) 0.01040(16) 0.0445(7) Uani 1 1 d . . . . .
F7 F 0.8315(3) 0.9112(2) 0.09697(12) 0.0298(5) Uani 1 1 d . . . . .
O4 O 0.7894(3) 0.6496(2) 0.05274(14) 0.0227(6) Uani 1 1 d . . . . .
O5 O 0.5227(3) 0.7619(2) 0.09049(13) 0.0198(5) Uani 1 1 d . . . . .
O6 O 0.6094(3) 0.7634(3) -0.04097(13) 0.0228(6) Uani 1 1 d . . . . .
C24 C 0.7773(5) 0.9024(4) 0.0312(2) 0.0233(8) 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 C4 2.081(3) . ?
I2 C19 2.081(3) . ?
F1 C10 1.355(4) . ?
N1 C1 1.342(4) . ?
N1 C3 1.341(4) . ?
N1 C21 1.486(4) . ?
N2 C18 1.351(4) . ?
N2 C20 1.338(4) . ?
N2 C22 1.483(4) . ?
C1 C2 1.374(5) . ?
C2 C5 1.405(5) . ?
C3 C4 1.378(5) . ?
C4 C5 1.409(5) . ?
C5 C6 1.432(5) . ?
C6 C7 1.192(5) . ?
C7 C8 1.437(5) . ?
C8 C9 1.399(5) . ?
C8 C12 1.397(5) . ?
C9 C10 1.381(5) . ?
C10 C11 1.380(5) . ?
C11 C13 1.397(5) . ?
C12 C13 1.397(5) . ?
C13 C14 1.440(5) . ?
C14 C15 1.201(5) . ?
C15 C16 1.426(5) . ?
C16 C17 1.400(5) . ?
C16 C19 1.408(5) . ?
C17 C18 1.366(5) . ?
C19 C20 1.377(5) . ?
S1 O1 1.446(3) . ?
S1 O2 1.445(3) . ?
S1 O3 1.438(3) . ?
S1 C23 1.821(4) . ?
F2 C23 1.348(4) . ?
F3 C23 1.337(5) . ?
F4 C23 1.327(5) . ?
S2 O4 1.451(3) . ?
S2 O5 1.442(2) . ?
S2 O6 1.442(3) . ?
S2 C24 1.825(4) . ?
F5 C24 1.338(4) . ?
F6 C24 1.319(4) . ?
F7 C24 1.327(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 C21 119.7(3) . . ?
C3 N1 C1 121.1(3) . . ?
C3 N1 C21 119.2(3) . . ?
C18 N2 C22 119.5(3) . . ?
C20 N2 C18 120.6(3) . . ?
C20 N2 C22 119.8(3) . . ?
N1 C1 C2 121.1(3) . . ?
C1 C2 C5 119.5(3) . . ?
N1 C3 C4 121.1(3) . . ?
C3 C4 I1 119.8(2) . . ?
C3 C4 C5 119.2(3) . . ?
C5 C4 I1 121.0(2) . . ?
C2 C5 C4 118.1(3) . . ?
C2 C5 C6 120.9(3) . . ?
C4 C5 C6 121.0(3) . . ?
C7 C6 C5 177.1(4) . . ?
C6 C7 C8 176.7(4) . . ?
C9 C8 C7 120.8(3) . . ?
C12 C8 C7 119.1(3) . . ?
C12 C8 C9 120.1(3) . . ?
C10 C9 C8 117.9(3) . . ?
F1 C10 C9 117.8(3) . . ?
F1 C10 C11 118.5(3) . . ?
C11 C10 C9 123.7(3) . . ?
C10 C11 C13 117.8(3) . . ?
C13 C12 C8 120.2(3) . . ?
C11 C13 C14 121.8(3) . . ?
C12 C13 C11 120.3(3) . . ?
C12 C13 C14 117.9(3) . . ?
C15 C14 C13 176.2(4) . . ?
C14 C15 C16 176.4(4) . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 C19 117.5(3) . . ?
C19 C16 C15 122.4(3) . . ?
C18 C17 C16 120.5(3) . . ?
N2 C18 C17 120.7(3) . . ?
C16 C19 I2 122.0(2) . . ?
C20 C19 I2 118.5(2) . . ?
C20 C19 C16 119.4(3) . . ?
N2 C20 C19 121.3(3) . . ?
O1 S1 C23 102.58(17) . . ?
O2 S1 O1 114.64(17) . . ?
O2 S1 C23 103.29(18) . . ?
O3 S1 O1 115.27(17) . . ?
O3 S1 O2 115.44(18) . . ?
O3 S1 C23 103.02(18) . . ?
F2 C23 S1 111.2(3) . . ?
F3 C23 S1 110.5(3) . . ?
F3 C23 F2 107.6(3) . . ?
F4 C23 S1 112.3(3) . . ?
F4 C23 F2 107.7(3) . . ?
F4 C23 F3 107.5(3) . . ?
O4 S2 C24 102.61(16) . . ?
O5 S2 O4 114.69(15) . . ?
O5 S2 O6 115.47(15) . . ?
O5 S2 C24 104.38(16) . . ?
O6 S2 O4 114.01(15) . . ?
O6 S2 C24 103.48(16) . . ?
F5 C24 S2 109.2(3) . . ?
F6 C24 S2 112.2(3) . . ?
F6 C24 F5 108.3(3) . . ?
F6 C24 F7 107.6(3) . . ?
F7 C24 S2 111.9(3) . . ?
F7 C24 F5 107.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
