# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_spilsj220928_0m
_database_code_depnum_ccdc_archive 'CCDC 2291802'
loop_
_audit_author_name
_audit_author_address
'Pim Puylaert'
;University of Bremen
Germany
;
_audit_update_record             
;
2023-08-30 deposited with the CCDC.	2024-03-14 downloaded from the CCDC.
;
_audit_creation_date             2023-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 I4 N O5, C F3 O3 S'
_chemical_formula_sum            'C19 H14 F3 I4 N O8 S'
_chemical_formula_weight         980.97
_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'

# end Validation Reply Form
_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      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3'
_space_group_name_Hall           'R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   34.2779(8)
_cell_length_b                   34.2779(8)
_cell_length_c                   13.8411(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     14084.1(8)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9399
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      36.31
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.628
_shelx_estimated_absorpt_T_min   0.433
_exptl_absorpt_coefficient_mu    4.104
_exptl_absorpt_correction_T_max  0.7223
_exptl_absorpt_correction_T_min  0.5638
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1121 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.7806.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.082
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             8172
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3.00 -3.00 1.00 0.0840
-3.00 1.00 1.00 0.0580
-3.00 0.00 -1.00 0.0240
-3.00 2.00 -1.00 0.0160
-2.00 -3.00 -1.00 0.0560
-2.00 2.00 1.00 0.0530
-1.00 2.00 2.00 0.0870
0.00 -1.00 0.00 0.0760
0.00 3.00 1.00 0.0630
0.00 0.00 -1.00 0.0670
0.00 2.00 -3.00 0.0510
0.00 3.00 -2.00 0.0350
1.00 2.00 0.00 0.0480
1.00 -1.00 0.00 0.1070
1.00 3.00 1.00 0.0660
1.00 -1.00 1.00 0.1030
1.00 -2.00 1.00 0.1030
2.00 -3.00 0.00 0.1070
2.00 -2.00 -1.00 0.1110
2.00 3.00 -1.00 0.0400
3.00 3.00 1.00 0.0660
3.00 0.00 1.00 0.0930
3.00 3.00 -2.00 0.0580

_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.125
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            262320
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.435
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                28638
_reflns_number_total             30489
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.420
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 13516 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.063(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         30489
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0160P)²+8.3392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0402
_refine_ls_wR_factor_ref         0.0409
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C32(H32), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C29(H29), C20(H20), C11(H11), C2(H2B), C22(H22)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C), C16(H16A,H16B,H16C), C34(H34A,H34B,
 H34C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   diffmap
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
I5 I 0.18078(2) 0.32068(2) 0.21665(2) 0.01251(3) Uani 1 1 d . . . . .
I1 I 0.15897(2) 0.35892(2) 0.80106(2) 0.01510(3) Uani 1 1 d . . . . .
I6 I 0.32704(2) 0.32798(2) 0.46457(2) 0.01722(3) Uani 1 1 d . . . . .
I3 I 0.23558(2) 0.32743(2) 0.69142(2) 0.01568(3) Uani 1 1 d . . . . .
I7 I 0.10128(2) 0.34847(2) 0.32748(2) 0.01597(3) Uani 1 1 d . . . . .
I4 I 0.09376(2) 0.22381(2) 0.39318(2) 0.01760(3) Uani 1 1 d . . . . .
I8 I 0.24285(2) 0.45482(2) 0.62587(2) 0.01887(3) Uani 1 1 d . . . . .
I2 I 0.00769(2) 0.35014(2) 0.57134(2) 0.02014(3) Uani 1 1 d . . . . .
S2 S 0.15824(2) 0.39360(2) 1.05070(5) 0.01300(10) Uani 1 1 d . . . . .
S1 S 0.05321(2) 0.56609(2) 0.63353(5) 0.01408(11) Uani 1 1 d . . . . .
F4 F 0.10985(7) 0.42802(7) 0.98632(13) 0.0266(4) Uani 1 1 d . . . . .
O1 O 0.07273(6) 0.32149(6) 0.67133(14) 0.0151(3) Uani 1 1 d . . . . .
F3 F 0.08661(9) 0.64042(7) 0.53172(16) 0.0398(6) Uani 1 1 d . . . . .
O15 O 0.18287(7) 0.41358(7) 0.96186(15) 0.0181(4) Uani 1 1 d . . . . .
O6 O 0.26623(6) 0.35862(6) 0.35061(14) 0.0139(3) Uani 1 1 d . . . . .
O13 O 0.06223(7) 0.54601(7) 0.55119(15) 0.0179(4) Uani 1 1 d . . . . .
O7 O 0.14780(7) 0.40677(8) 0.50593(16) 0.0208(4) Uani 1 1 d . . . . .
F2 F 0.08739(10) 0.65044(7) 0.68525(17) 0.0461(6) Uani 1 1 d . . . . .
F1 F 0.13471(7) 0.63408(7) 0.62077(19) 0.0421(6) Uani 1 1 d . . . . .
O16 O 0.12459(8) 0.34659(7) 1.04297(18) 0.0252(4) Uani 1 1 d . . . . .
O11 O 0.06864(7) 0.55768(7) 0.72505(14) 0.0177(4) Uani 1 1 d . . . . .
O2 O 0.18746(7) 0.26826(8) 0.51485(16) 0.0195(4) Uani 1 1 d . . . . .
O12 O 0.00916(7) 0.56082(9) 0.63455(18) 0.0291(5) Uani 1 1 d . . . . .
O5 O 0.16765(8) 0.48708(8) 0.55155(19) 0.0286(5) Uani 1 1 d . . . . .
O14 O 0.18695(7) 0.40573(7) 1.13590(15) 0.0188(4) Uani 1 1 d . . . . .
F6 F 0.09169(10) 0.40033(11) 1.12796(18) 0.0555(8) Uani 1 1 d . . . . .
O10 O 0.16560(8) 0.18792(8) 0.45395(17) 0.0268(5) Uani 1 1 d . . . . .
C4 C 0.07586(10) 0.42960(10) 0.6906(2) 0.0201(5) Uani 1 1 d . . . . .
H4 H 0.057293 0.441863 0.673877 0.024 Uiso 1 1 calc R U . . .
C19 C 0.21592(8) 0.28911(8) 0.26732(18) 0.0129(4) Uani 1 1 d . . . . .
N1 N 0.12936(9) 0.52208(9) 0.5890(2) 0.0239(5) Uani 1 1 d . . . . .
C21 C 0.23043(9) 0.22777(9) 0.2667(2) 0.0160(4) Uani 1 1 d . . . . .
C7 C 0.14419(9) 0.32234(9) 0.67229(18) 0.0144(4) Uani 1 1 d . . . . .
C6 C 0.08761(9) 0.36602(9) 0.69351(19) 0.0145(4) Uani 1 1 d . . . . .
C29 C 0.24943(8) 0.39761(8) 0.46866(18) 0.0132(4) Uani 1 1 d . . . . .
H29 H 0.278109 0.407374 0.496941 0.016 Uiso 1 1 calc R U . . .
N2 N 0.20096(8) 0.15102(8) 0.40340(18) 0.0176(4) Uani 1 1 d . . . . .
C23 C 0.27660(8) 0.29492(8) 0.36222(18) 0.0134(4) Uani 1 1 d . . . . .
F5 F 0.15221(10) 0.46289(9) 1.1079(2) 0.0570(8) Uani 1 1 d . . . . .
C5 C 0.06270(9) 0.38559(10) 0.66304(19) 0.0167(5) Uani 1 1 d . . . . .
C26 C 0.16459(8) 0.36850(9) 0.38633(19) 0.0139(4) Uani 1 1 d . . . . .
C12 C 0.10263(8) 0.31008(9) 0.63167(19) 0.0143(4) Uani 1 1 d . . . . .
C30 C 0.23549(8) 0.36927(8) 0.38892(18) 0.0119(4) Uani 1 1 d . . . . .
C10 C 0.11570(9) 0.26655(9) 0.51302(19) 0.0147(4) Uani 1 1 d . . . . .
C20 C 0.20355(9) 0.24578(9) 0.23757(19) 0.0152(4) Uani 1 1 d . . . . .
H20 H 0.177615 0.228830 0.198592 0.018 Uiso 1 1 calc R U . . .
C8 C 0.17258(8) 0.30865(9) 0.63287(18) 0.0134(4) Uani 1 1 d . . . . .
C24 C 0.25178(8) 0.31423(8) 0.32762(18) 0.0121(4) Uani 1 1 d . . . . .
C27 C 0.17773(8) 0.39676(8) 0.46816(18) 0.0135(4) Uani 1 1 d . . . . .
C25 C 0.19411(8) 0.35612(8) 0.34750(17) 0.0117(4) Uani 1 1 d . . . . .
C1 C 0.12602(9) 0.39246(9) 0.74895(19) 0.0157(4) Uani 1 1 d . . . . .
O3 O 0.22505(9) 0.54953(10) 0.7269(2) 0.0391(6) Uani 1 1 d . . . . .
C9 C 0.15840(9) 0.27984(9) 0.55232(19) 0.0147(4) Uani 1 1 d . . . . .
O9 O 0.14745(9) 0.06743(7) 0.33607(18) 0.0302(5) Uani 1 1 d . . . . .
C31 C 0.21886(10) 0.18112(9) 0.2364(2) 0.0188(5) Uani 1 1 d . . . . .
H31A H 0.246430 0.178648 0.236555 0.023 Uiso 1 1 calc R U . . .
H31B H 0.206570 0.175226 0.169952 0.023 Uiso 1 1 calc R U . . .
O8 O 0.16914(9) 0.09082(8) 0.18370(17) 0.0288(5) Uani 1 1 d . . . . .
C11 C 0.08822(8) 0.28179(9) 0.5514(2) 0.0150(4) Uani 1 1 d . . . . .
H11 H 0.059753 0.272932 0.523024 0.018 Uiso 1 1 calc R U . . .
C28 C 0.22067(8) 0.41152(9) 0.50661(18) 0.0139(4) Uani 1 1 d . . . . .
C38 C 0.12620(11) 0.42286(12) 1.0691(2) 0.0247(6) Uani 1 1 d . . . . .
C2 C 0.14132(10) 0.43716(10) 0.77165(19) 0.0186(5) Uani 1 1 d . . . . .
H2B H 0.168580 0.454429 0.806447 0.022 Uiso 1 1 calc R U . . .
C32 C 0.18404(9) 0.14613(9) 0.30559(19) 0.0173(5) Uani 1 1 d . . . . .
H32 H 0.157796 0.151285 0.307618 0.021 Uiso 1 1 calc R U . . .
C22 C 0.26641(9) 0.25245(9) 0.32962(19) 0.0160(4) Uani 1 1 d . . . . .
H22 H 0.284273 0.239997 0.350541 0.019 Uiso 1 1 calc R U . . .
C3 C 0.11550(10) 0.45609(10) 0.7419(2) 0.0205(5) Uani 1 1 d . . . . .
C35 C 0.19169(10) 0.17341(10) 0.4707(2) 0.0211(5) Uani 1 1 d . . . . .
C37 C 0.09225(11) 0.62631(9) 0.6172(2) 0.0236(6) Uani 1 1 d . . . . .
C18 C 0.11031(13) 0.47955(13) 0.4411(3) 0.0321(7) Uani 1 1 d . . . . .
H18A H 0.130212 0.487261 0.384910 0.048 Uiso 1 1 calc R U . . .
H18B H 0.091550 0.493550 0.434581 0.048 Uiso 1 1 calc R U . . .
H18C H 0.090968 0.446764 0.445004 0.048 Uiso 1 1 calc R U . . .
C17 C 0.13817(11) 0.49651(11) 0.5313(2) 0.0250(6) Uani 1 1 d . . . . .
C13 C 0.12980(11) 0.50496(11) 0.7646(2) 0.0246(6) Uani 1 1 d . . . . .
H13A H 0.150981 0.514915 0.819862 0.029 Uiso 1 1 calc R U . . .
H13B H 0.102858 0.506292 0.785405 0.029 Uiso 1 1 calc R U . . .
C36 C 0.21540(14) 0.18146(16) 0.5646(3) 0.0400(9) Uani 1 1 d . . . . .
H36A H 0.245899 0.207403 0.558739 0.060 Uiso 1 1 calc R U . . .
H36B H 0.217152 0.154729 0.582622 0.060 Uiso 1 1 calc R U . . .
H36C H 0.198828 0.187564 0.614352 0.060 Uiso 1 1 calc R U . . .
O4 O 0.21883(9) 0.58098(10) 0.5909(2) 0.0389(6) Uani 1 1 d . . . . .
C14 C 0.15235(10) 0.53848(10) 0.6809(2) 0.0242(6) Uani 1 1 d . . . . .
H14 H 0.149871 0.565563 0.697391 0.029 Uiso 1 1 calc R U . . .
C33 C 0.16676(10) 0.09857(9) 0.2687(2) 0.0197(5) Uani 1 1 d . . . . .
C15 C 0.20286(12) 0.55538(12) 0.6692(3) 0.0331(8) Uani 1 1 d . . . . .
C16 C 0.26667(18) 0.5961(2) 0.5720(5) 0.0673(16) Uani 1 1 d . . . . .
H16A H 0.276309 0.614263 0.512909 0.101 Uiso 1 1 calc R U . . .
H16B H 0.270480 0.569773 0.564002 0.101 Uiso 1 1 calc R U . . .
H16C H 0.285001 0.614243 0.626505 0.101 Uiso 1 1 calc R U . . .
C34 C 0.12879(17) 0.02122(12) 0.3045(3) 0.0454(10) Uani 1 1 d . . . . .
H34A H 0.121160 0.018996 0.235689 0.068 Uiso 1 1 calc R U . . .
H34B H 0.101559 0.001802 0.341830 0.068 Uiso 1 1 calc R U . . .
H34C H 0.151012 0.011580 0.314477 0.068 Uiso 1 1 calc R U . . .
H1 H 0.1048(11) 0.5256(11) 0.579(2) 0.008(7) Uiso 1 1 d . . . . .
H2 H 0.2161(15) 0.1412(16) 0.411(3) 0.034(12) Uiso 1 1 d . . . . .
H2A H 0.1837(15) 0.2470(15) 0.495(3) 0.034(12) Uiso 1 1 d . . . . .
H7 H 0.1634(12) 0.4360(13) 0.534(3) 0.018(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I5 C19 2.102(2) . ?
I5 C25 2.100(2) . ?
I1 C7 2.091(3) . ?
I1 C1 2.101(2) . ?
I6 C23 2.079(3) . ?
I3 C8 2.084(2) . ?
I7 C26 2.087(2) . ?
I4 C10 2.089(3) . ?
I8 C28 2.092(2) . ?
I2 C5 2.086(3) . ?
S2 O15 1.454(2) . ?
S2 O16 1.442(2) . ?
S2 O14 1.457(2) . ?
S2 C38 1.838(3) . ?
S1 O13 1.442(2) . ?
S1 O11 1.456(2) . ?
S1 O12 1.428(2) . ?
S1 C37 1.828(3) . ?
F4 C38 1.325(3) . ?
O1 C6 1.381(3) . ?
O1 C12 1.380(3) . ?
F3 C37 1.328(4) . ?
O6 C30 1.382(3) . ?
O6 C24 1.381(3) . ?
O7 C27 1.340(3) . ?
O7 H7 0.95(4) . ?
F2 C37 1.318(4) . ?
F1 C37 1.343(4) . ?
O2 C9 1.347(3) . ?
O2 H2A 0.73(5) . ?
O5 C17 1.237(4) . ?
F6 C38 1.322(4) . ?
O10 C35 1.243(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(4) . ?
C4 C3 1.393(4) . ?
C19 C20 1.388(3) . ?
C19 C24 1.375(4) . ?
N1 C17 1.327(4) . ?
N1 C14 1.454(4) . ?
N1 H1 0.92(3) . ?
C21 C20 1.401(4) . ?
C21 C31 1.502(4) . ?
C21 C22 1.397(4) . ?
C7 C12 1.387(3) . ?
C7 C8 1.386(3) . ?
C6 C5 1.389(4) . ?
C6 C1 1.397(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(3) . ?
C29 C28 1.395(3) . ?
N2 C32 1.449(4) . ?
N2 C35 1.342(4) . ?
N2 H2 0.75(5) . ?
C23 C24 1.398(3) . ?
C23 C22 1.391(4) . ?
F5 C38 1.320(4) . ?
C26 C27 1.410(4) . ?
C26 C25 1.387(3) . ?
C12 C11 1.393(4) . ?
C30 C25 1.380(3) . ?
C10 C9 1.407(4) . ?
C10 C11 1.391(4) . ?
C20 H20 0.9500 . ?
C8 C9 1.405(4) . ?
C27 C28 1.400(4) . ?
C1 C2 1.385(4) . ?
O3 C15 1.187(4) . ?
O9 C33 1.320(4) . ?
O9 C34 1.448(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.532(4) . ?
O8 C33 1.217(4) . ?
C11 H11 0.9500 . ?
C2 H2B 0.9500 . ?
C2 C3 1.396(4) . ?
C32 H32 1.0000 . ?
C32 C33 1.518(4) . ?
C22 H22 0.9500 . ?
C3 C13 1.524(4) . ?
C35 C36 1.483(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C17 1.501(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.540(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
O4 C15 1.328(5) . ?
O4 C16 1.475(5) . ?
C14 H14 1.0000 . ?
C14 C15 1.535(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 I5 C19 89.72(9) . . ?
C7 I1 C1 90.01(10) . . ?
O15 S2 O14 113.55(13) . . ?
O15 S2 C38 102.98(14) . . ?
O16 S2 O15 114.52(13) . . ?
O16 S2 O14 115.31(13) . . ?
O16 S2 C38 104.95(15) . . ?
O14 S2 C38 103.59(13) . . ?
O13 S1 O11 114.03(12) . . ?
O13 S1 C37 103.33(14) . . ?
O11 S1 C37 101.41(13) . . ?
O12 S1 O13 114.38(14) . . ?
O12 S1 O11 115.60(13) . . ?
O12 S1 C37 105.95(16) . . ?
C12 O1 C6 119.0(2) . . ?
C24 O6 C30 118.59(19) . . ?
C27 O7 H7 109(2) . . ?
C9 O2 H2A 131(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(2) . . ?
C20 C19 I5 120.33(19) . . ?
C24 C19 I5 116.31(17) . . ?
C24 C19 C20 123.3(2) . . ?
C17 N1 C14 121.6(2) . . ?
C17 N1 H1 122(2) . . ?
C14 N1 H1 116(2) . . ?
C20 C21 C31 120.5(2) . . ?
C22 C21 C20 119.3(2) . . ?
C22 C21 C31 120.1(2) . . ?
C12 C7 I1 115.56(18) . . ?
C8 C7 I1 122.54(18) . . ?
C8 C7 C12 121.8(2) . . ?
O1 C6 C5 119.3(2) . . ?
O1 C6 C1 123.1(2) . . ?
C5 C6 C1 117.5(2) . . ?
C30 C29 H29 120.5 . . ?
C30 C29 C28 118.9(2) . . ?
C28 C29 H29 120.5 . . ?
C32 N2 H2 114(3) . . ?
C35 N2 C32 121.3(2) . . ?
C35 N2 H2 125(3) . . ?
C24 C23 I6 120.83(18) . . ?
C22 C23 I6 119.79(18) . . ?
C22 C23 C24 119.4(2) . . ?
C4 C5 I2 120.37(19) . . ?
C6 C5 I2 119.9(2) . . ?
C6 C5 C4 119.7(2) . . ?
C27 C26 I7 117.52(17) . . ?
C25 C26 I7 123.10(19) . . ?
C25 C26 C27 119.4(2) . . ?
O1 C12 C7 123.3(2) . . ?
O1 C12 C11 117.3(2) . . ?
C7 C12 C11 119.2(2) . . ?
O6 C30 C29 116.7(2) . . ?
C25 C30 O6 123.3(2) . . ?
C25 C30 C29 119.8(2) . . ?
C9 C10 I4 119.06(18) . . ?
C11 C10 I4 119.53(19) . . ?
C11 C10 C9 121.4(2) . . ?
C19 C20 C21 118.0(2) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C7 C8 I3 122.47(19) . . ?
C7 C8 C9 119.7(2) . . ?
C9 C8 I3 117.81(17) . . ?
O6 C24 C23 118.4(2) . . ?
C19 C24 O6 123.0(2) . . ?
C19 C24 C23 118.5(2) . . ?
O7 C27 C26 117.8(2) . . ?
O7 C27 C28 124.1(2) . . ?
C28 C27 C26 118.1(2) . . ?
C26 C25 I5 122.03(18) . . ?
C30 C25 I5 115.98(17) . . ?
C30 C25 C26 121.8(2) . . ?
C6 C1 I1 115.08(19) . . ?
C2 C1 I1 121.2(2) . . ?
C2 C1 C6 123.7(2) . . ?
O2 C9 C10 124.0(2) . . ?
O2 C9 C8 117.7(2) . . ?
C8 C9 C10 118.2(2) . . ?
C33 O9 C34 116.1(3) . . ?
C21 C31 H31A 109.6 . . ?
C21 C31 H31B 109.6 . . ?
C21 C31 C32 110.3(2) . . ?
H31A C31 H31B 108.1 . . ?
C32 C31 H31A 109.6 . . ?
C32 C31 H31B 109.6 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.2 . . ?
C29 C28 I8 118.13(18) . . ?
C29 C28 C27 121.9(2) . . ?
C27 C28 I8 119.97(18) . . ?
F4 C38 S2 111.2(2) . . ?
F6 C38 S2 111.8(2) . . ?
F6 C38 F4 107.2(3) . . ?
F5 C38 S2 110.3(2) . . ?
F5 C38 F4 108.9(3) . . ?
F5 C38 F6 107.3(3) . . ?
C1 C2 H2B 121.0 . . ?
C1 C2 C3 118.0(3) . . ?
C3 C2 H2B 121.0 . . ?
N2 C32 C31 112.5(2) . . ?
N2 C32 H32 107.3 . . ?
N2 C32 C33 110.9(2) . . ?
C31 C32 H32 107.3 . . ?
C33 C32 C31 111.3(2) . . ?
C33 C32 H32 107.3 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.3(2) . . ?
C23 C22 H22 119.3 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 C13 119.6(2) . . ?
C2 C3 C13 121.3(3) . . ?
O10 C35 N2 121.5(3) . . ?
O10 C35 C36 121.7(3) . . ?
N2 C35 C36 116.7(3) . . ?
F3 C37 S1 111.3(2) . . ?
F3 C37 F1 107.5(3) . . ?
F2 C37 S1 111.7(2) . . ?
F2 C37 F3 108.7(3) . . ?
F2 C37 F1 108.3(3) . . ?
F1 C37 S1 109.2(2) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
O5 C17 N1 121.4(3) . . ?
O5 C17 C18 122.1(3) . . ?
N1 C17 C18 116.5(3) . . ?
C3 C13 H13A 108.4 . . ?
C3 C13 H13B 108.4 . . ?
C3 C13 C14 115.5(2) . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C15 O4 C16 113.3(3) . . ?
N1 C14 C13 113.4(3) . . ?
N1 C14 H14 106.1 . . ?
N1 C14 C15 110.1(3) . . ?
C13 C14 H14 106.1 . . ?
C15 C14 C13 114.3(3) . . ?
C15 C14 H14 106.1 . . ?
O9 C33 C32 113.5(2) . . ?
O8 C33 O9 124.6(3) . . ?
O8 C33 C32 121.8(3) . . ?
O3 C15 O4 125.0(4) . . ?
O3 C15 C14 124.2(4) . . ?
O4 C15 C14 110.5(3) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O9 C34 H34A 109.5 . . ?
O9 C34 H34B 109.5 . . ?
O9 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I5 C19 C20 C21 174.56(19) . . . . ?
I5 C19 C24 O6 -3.5(3) . . . . ?
I5 C19 C24 C23 -179.17(18) . . . . ?
I1 C7 C12 O1 1.0(3) . . . . ?
I1 C7 C12 C11 -173.49(19) . . . . ?
I1 C7 C8 I3 -5.1(3) . . . . ?
I1 C7 C8 C9 172.75(19) . . . . ?
I1 C1 C2 C3 -174.3(2) . . . . ?
I6 C23 C24 O6 10.5(3) . . . . ?
I6 C23 C24 C19 -173.66(18) . . . . ?
I6 C23 C22 C21 174.9(2) . . . . ?
I3 C8 C9 O2 -3.7(3) . . . . ?
I3 C8 C9 C10 179.25(19) . . . . ?
I7 C26 C27 O7 3.7(3) . . . . ?
I7 C26 C27 C28 -178.15(19) . . . . ?
I7 C26 C25 I5 6.0(3) . . . . ?
I7 C26 C25 C30 -178.90(19) . . . . ?
I4 C10 C9 O2 3.0(4) . . . . ?
I4 C10 C9 C8 179.92(18) . . . . ?
I4 C10 C11 C12 179.63(19) . . . . ?
O1 C6 C5 I2 -7.1(3) . . . . ?
O1 C6 C5 C4 175.8(2) . . . . ?
O1 C6 C1 I1 -2.0(3) . . . . ?
O1 C6 C1 C2 180.0(2) . . . . ?
O1 C12 C11 C10 -175.2(2) . . . . ?
O15 S2 C38 F4 40.6(3) . . . . ?
O15 S2 C38 F6 160.4(2) . . . . ?
O15 S2 C38 F5 -80.3(3) . . . . ?
O6 C30 C25 I5 -2.7(3) . . . . ?
O6 C30 C25 C26 -178.1(2) . . . . ?
O13 S1 C37 F3 55.8(3) . . . . ?
O13 S1 C37 F2 177.6(2) . . . . ?
O13 S1 C37 F1 -62.7(2) . . . . ?
O7 C27 C28 I8 -3.5(4) . . . . ?
O7 C27 C28 C29 175.4(2) . . . . ?
O16 S2 C38 F4 -79.6(3) . . . . ?
O16 S2 C38 F6 40.2(3) . . . . ?
O16 S2 C38 F5 159.5(3) . . . . ?
O11 S1 C37 F3 174.2(2) . . . . ?
O11 S1 C37 F2 -64.1(3) . . . . ?
O11 S1 C37 F1 55.6(2) . . . . ?
O12 S1 C37 F3 -64.7(3) . . . . ?
O12 S1 C37 F2 57.0(3) . . . . ?
O12 S1 C37 F1 176.7(2) . . . . ?
O14 S2 C38 F4 159.1(2) . . . . ?
O14 S2 C38 F6 -81.1(3) . . . . ?
O14 S2 C38 F5 38.2(3) . . . . ?
C4 C3 C13 C14 -79.1(4) . . . . ?
N1 C14 C15 O3 -140.5(3) . . . . ?
N1 C14 C15 O4 45.7(3) . . . . ?
C21 C31 C32 N2 -63.0(3) . . . . ?
C21 C31 C32 C33 171.8(2) . . . . ?
C7 C12 C11 C10 -0.4(4) . . . . ?
C7 C8 C9 O2 178.4(2) . . . . ?
C7 C8 C9 C10 1.3(4) . . . . ?
C6 O1 C12 C7 52.3(3) . . . . ?
C6 O1 C12 C11 -133.1(2) . . . . ?
C6 C1 C2 C3 3.7(4) . . . . ?
C29 C30 C25 I5 171.91(18) . . . . ?
C29 C30 C25 C26 -3.5(4) . . . . ?
N2 C32 C33 O9 35.2(3) . . . . ?
N2 C32 C33 O8 -147.9(3) . . . . ?
C5 C4 C3 C2 -4.0(4) . . . . ?
C5 C4 C3 C13 176.1(3) . . . . ?
C5 C6 C1 I1 175.49(19) . . . . ?
C5 C6 C1 C2 -2.6(4) . . . . ?
C26 C27 C28 I8 178.47(19) . . . . ?
C26 C27 C28 C29 -2.6(4) . . . . ?
C12 O1 C6 C5 131.1(3) . . . . ?
C12 O1 C6 C1 -51.5(3) . . . . ?
C12 C7 C8 I3 179.1(2) . . . . ?
C12 C7 C8 C9 -3.1(4) . . . . ?
C30 O6 C24 C19 54.9(3) . . . . ?
C30 O6 C24 C23 -129.5(2) . . . . ?
C30 C29 C28 I8 -179.33(18) . . . . ?
C30 C29 C28 C27 1.7(4) . . . . ?
C20 C19 C24 O6 174.5(2) . . . . ?
C20 C19 C24 C23 -1.2(4) . . . . ?
C20 C21 C31 C32 -84.5(3) . . . . ?
C20 C21 C22 C23 -1.3(4) . . . . ?
C8 C7 C12 O1 177.1(2) . . . . ?
C8 C7 C12 C11 2.6(4) . . . . ?
C24 O6 C30 C29 134.3(2) . . . . ?
C24 O6 C30 C25 -51.0(3) . . . . ?
C24 C19 C20 C21 -3.3(4) . . . . ?
C24 C23 C22 C21 -3.2(4) . . . . ?
C27 C26 C25 I5 -172.56(18) . . . . ?
C27 C26 C25 C30 2.6(4) . . . . ?
C25 C26 C27 O7 -177.7(2) . . . . ?
C25 C26 C27 C28 0.5(4) . . . . ?
C1 C6 C5 I2 175.36(19) . . . . ?
C1 C6 C5 C4 -1.8(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C13 179.6(3) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C31 C21 C20 C19 -179.7(2) . . . . ?
C31 C21 C22 C23 -177.1(2) . . . . ?
C31 C32 C33 O9 161.3(2) . . . . ?
C31 C32 C33 O8 -21.8(4) . . . . ?
C11 C10 C9 O2 -176.0(2) . . . . ?
C11 C10 C9 C8 0.9(4) . . . . ?
C28 C29 C30 O6 176.3(2) . . . . ?
C28 C29 C30 C25 1.3(4) . . . . ?
C2 C3 C13 C14 101.0(3) . . . . ?
C32 N2 C35 O10 5.4(5) . . . . ?
C32 N2 C35 C36 -172.4(3) . . . . ?
C22 C21 C20 C19 4.5(4) . . . . ?
C22 C21 C31 C32 91.2(3) . . . . ?
C22 C23 C24 O6 -171.4(2) . . . . ?
C22 C23 C24 C19 4.5(4) . . . . ?
C3 C4 C5 I2 -172.1(2) . . . . ?
C3 C4 C5 C6 5.1(4) . . . . ?
C3 C13 C14 N1 44.5(3) . . . . ?
C3 C13 C14 C15 -82.9(3) . . . . ?
C35 N2 C32 C31 97.4(3) . . . . ?
C35 N2 C32 C33 -137.2(3) . . . . ?
C17 N1 C14 C13 -86.1(4) . . . . ?
C17 N1 C14 C15 43.4(4) . . . . ?
C13 C14 C15 O3 -11.5(5) . . . . ?
C13 C14 C15 O4 174.7(3) . . . . ?
C14 N1 C17 O5 -3.0(5) . . . . ?
C14 N1 C17 C18 176.6(3) . . . . ?
C16 O4 C15 O3 9.8(6) . . . . ?
C16 O4 C15 C14 -176.4(4) . . . . ?
C34 O9 C33 O8 1.0(5) . . . . ?
C34 O9 C33 C32 177.8(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.304 1065.5 260.9 ?
2 0.333 0.667 -0.579 1065.5 260.9 ?
3 0.667 0.333 -0.913 1065.5 260.9 ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT094_spilsj220928_0m     
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.09 Report
RESPONSE: Residual densities up to 1.4 are found next to each of the four 
iodine heavy atoms per molecule. We usually obtain such values for 
maximum residual density as well as the maximum/minimum ratio for iodine-
containing compounds.
;
_vrf_PLAT220_spilsj220928_0m     
;
PROBLEM: NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        5.0 Ratio 
RESPONSE: Alerts 220, 222, 230, 245 and 245 are likewise results of vibrating 
parts of the molecule. As stated above, the chemical composition was validated 
by other analytical techniques.
;
_vrf_PLAT222_spilsj220928_0m     
;
PROBLEM: NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range       10.0 Ratio 
RESPONSE: Please refer to alert 220
;
# start Validation Reply Form
_vrf_PLAT230_spilsj220928_0m     
;
PROBLEM: Hirshfeld Test Diff for    O4       --C15      .        9.0 s.u.  
RESPONSE: The ester functionality consisting of C14, C15, C16, O3, and O4 appears 
somewhat dynamic, which affects the ellipsoids and raises alarms during the 
Hirshfeld test. Attempted RIGU restraints did not improve the model. 
The chemical composition has been validated by other established analytical 
methods as described in the paper. 
;
_vrf_PLAT245_spilsj220928_0m     
;
PROBLEM: U(iso) H1        Smaller than U(eq) N1        by      0.016 Ang**2
RESPONSE: Please refer to alert 220
;
_vrf_PLAT250_spilsj220928_0m     
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.5 Note  
RESPONSE: Please refer to alert 220
;
_vrf_PLAT352_spilsj220928_0m     
;
PROBLEM: Short  N-H (X0.87,N1.01A)  N2       - H2       .       0.75 Ang.  
RESPONSE: H2 was refined freely as usual for hydrogen attached to 
heteroatoms; in contrast to N1-H1, hydrogen-bridging with the 
triflate anion was not recognised resulting in an underestimation
of the N2-H2 distance.
;
_vrf_PLAT987_spilsj220928_0m     
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check 
RESPONSE: We checked using both APEX4 and PLATON, but found no evidence of 
twinning. Additionally, implementing a tentative twin law in Olex2 with 
ShelXL plugin did not improve the model.
;
