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

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

data_tm-03-67
_database_code_depnum_ccdc_archive 'CCDC 2294510'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;EPFL
Switzerland
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-08-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 Cl F6 I O2'
_chemical_formula_sum            'C21 H24 Cl F6 I O2'
_chemical_formula_weight         584.75
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H24 O2 F6 Cl1 I1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.94012(13)
_cell_length_b                   12.9377(2)
_cell_length_c                   9.96505(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.8561(13)
_cell_angle_gamma                90
_cell_volume                     1149.99(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10897
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.7220
_cell_measurement_theta_min      3.4150
_shelx_estimated_absorpt_T_max   0.257
_shelx_estimated_absorpt_T_min   0.166
_exptl_absorpt_coefficient_mu    12.598
_exptl_absorpt_correction_T_max  0.485
_exptl_absorpt_correction_T_min  0.147
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             580
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 -1 0.1028
1 2 -2 0.0749
1 2 -1 0.0888
1 -2 -2 0.1089
2 2 -1 0.0796
2 -1 -2 0.0919
2 -1 -1 0.0867
-2 1 1 0.1198
-2 -1 0 0.0943
2 1 0 0.0748
6 -2 -1 0.0804
2 -7 -2 0.1072
-1 8 2 0.0992
2 2 1 0.0806
2 1 1 0.0792
5 -4 1 0.0862
1 -2 0 0.0995
2 1 2 0.0792
1 -1 1 0.0868
1 -2 1 0.0816
0 1 2 0.0882
-1 -5 5 0.0739
-5 -3 3 0.0836
-4 4 4 0.1049
-5 -4 0 0.0897
-1 0 -2 0.0793
-1 2 -2 0.0872
1 5 -5 0.0680
0 -1 -6 0.0911
2 1 6 0.0723
1 -5 5 0.0721
1 7 3 0.0908
-3 -5 4 0.0792
-2 2 6 0.0842
-2 -1 -2 0.0740
-4 6 -2 0.1020

_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.148
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -2.0000 -1.0000 0.0804 0.0432 0.2691
1.0000 2.0000 -2.0000 0.3327 0.1901 -0.1690
1.0000 2.0000 -1.0000 0.1850 0.1684 -0.2106
1.0000 -2.0000 -2.0000 0.1982 0.2331 0.2860
2.0000 2.0000 -1.0000 0.1551 0.3367 -0.2353
2.0000 -1.0000 -2.0000 0.2019 0.3906 0.1475
2.0000 -1.0000 -1.0000 0.0543 0.3690 0.1059
-2.0000 1.0000 1.0000 -0.0543 -0.3690 -0.1059
-2.0000 -1.0000 -0.0000 0.0261 -0.3258 0.1632
2.0000 1.0000 0.0000 -0.0261 0.3258 -0.1632
5.6158 -1.9538 -1.0513 -0.0782 0.9888 0.1272
2.1742 -7.4556 -1.8820 -0.0377 0.4868 0.8727
-0.9041 7.9612 1.8529 0.0210 -0.2779 -0.9604
2.0000 2.0000 1.0000 -0.1402 0.2934 -0.3186
2.0000 1.0000 1.0000 -0.1738 0.3041 -0.2048
4.9772 -3.7540 1.2677 -0.4621 0.8505 0.2513
1.0000 -2.0000 0.0000 -0.0971 0.1898 0.2028
2.0000 1.0000 2.0000 -0.3215 0.2825 -0.2464
1.0000 -1.0000 1.0000 -0.2112 0.1574 0.0474
1.0000 -2.0000 1.0000 -0.2448 0.1681 0.1612
0.0000 1.0000 2.0000 -0.2617 -0.0541 -0.1970
-0.6299 -4.6217 5.3906 -0.9325 -0.1730 0.3170
-4.8128 -3.2951 2.9296 -0.3995 -0.8379 0.3719
-3.8130 3.8629 4.1397 -0.3675 -0.7728 -0.5174
-5.0394 -4.0631 -0.3286 0.0625 -0.7972 0.6005
-1.0000 -0.0000 -2.0000 0.3252 -0.1250 0.1079
-1.0000 2.0000 -2.0000 0.3924 -0.1465 -0.1196
0.7023 5.4897 -4.8740 0.8832 0.1647 -0.4391
0.0893 -1.2406 -6.3896 0.8991 0.1667 0.4048
1.5449 0.8332 6.0731 -0.9149 0.1195 -0.3856
1.0634 -4.9201 5.0155 -0.9377 0.1233 0.3247
1.0786 7.0098 3.2627 -0.2784 0.0355 -0.9598
-2.7085 -5.4128 4.1117 -0.7081 -0.4866 0.5116
-2.0710 2.3909 5.8975 -0.7285 -0.5019 -0.4662
-2.0000 -1.0000 -2.0000 0.3215 -0.2825 0.2464
-3.6291 5.5349 -2.4238 0.6524 -0.6177 -0.4391

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12606
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.067
_diffrn_reflns_theta_min         4.447
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00  -8.00   1.00    2.00    --  -40.66 -23.00-100.00  110
  2  ω    -43.00 -18.00   1.00    2.00    --  -40.66  23.00  65.00   25
  3  ω     48.00 107.00   1.00    2.00    --   40.66  23.00  65.00   59
  4  ω     98.00 135.00   1.00    8.00    --  112.00  23.00  65.00   37
  5  ω    153.00 178.00   1.00    8.00    --  112.00  23.00  65.00   25
  6  ω     59.00  98.00   1.00    8.00    --  112.00 -23.00-100.00   39
  7  ω    -77.00 -50.00   1.00    2.00    --  -40.66 -57.00-180.00   27
  8  ω   -112.00 -16.00   1.00    2.00    --  -40.66 -38.00-180.00   96
  9  ω     30.00  89.00   1.00    2.00    --   40.66-125.00 150.00   59
 10  ω     28.00  95.00   1.00    2.00    --   40.66-125.00 -30.00   67
 11  ω     32.00  59.00   1.00    2.00    --   40.66  38.00-150.00   27
 12  ω      8.00  35.00   1.00    2.00    --   40.66 -99.00-120.00   27
 13  ω     -5.00  20.00   1.00    2.00    --   40.66 -23.00-100.00   25
 14  ω     14.00  87.00   1.00    2.00    --   40.66  57.00-180.00   73
 15  ω     20.00  47.00   1.00    2.00    --   40.66  57.00-120.00   27
 16  ω     83.00 109.00   1.00    8.00    --  112.00  61.00 120.00   26
 17  ω    126.00 172.00   1.00    8.00    --  112.00  77.00  60.00   46
 18  ω     86.00 178.00   1.00    8.00    --  112.00  45.00 150.00   92
 19  ω     86.00 152.00   1.00    8.00    --  112.00  48.00 126.52   66
 20  ω     29.00  66.00   1.00    8.00    --  112.00 -94.00 120.00   37
 21  ω    144.00 170.00   1.00    8.00    --  112.00  55.00 170.74   26
 22  ω     31.00  81.00   1.00    8.00    --  112.00 -94.00 -60.00   50
 23  ω     84.00 113.00   1.00    8.00    --  112.00  55.00 170.74   29
 24  ω     30.00  98.00   1.00    8.00    --  112.00 -94.00 -30.00   68
 25  ω    137.00 164.00   1.00    8.00    --  112.00  61.00  90.00   27
 26  ω    114.00 177.00   1.00    8.00    --  112.00  61.00-150.00   63
 27  ω     87.00 141.00   1.00    8.00    --  112.00  45.00-150.00   54
 28  ω     59.00  96.00   1.00    8.00    --  112.00 -61.00  90.00   37
 29  ω     87.00 112.00   1.00    8.00    --  112.00  45.00-120.00   25
 30  ω     84.00 109.00   1.00    8.00    --  112.00  61.00 150.00   25
 31  ω     84.00 111.00   1.00    8.00    --  112.00  61.00  90.00   27
 32  ω     87.00 114.00   1.00    8.00    --  112.00  45.00 120.00   27
 33  ω     86.00 113.00   1.00    8.00    --  112.00  53.00-151.57   27
 34  ω     77.00 128.00   1.00    8.00    --  112.00 -45.00 -60.00   51
 35  ω     84.00 109.00   1.00    8.00    --  112.00  61.00-120.00   25
 36  ω     83.00 110.00   1.00    8.00    --  112.00  62.00 153.81   27
 37  ω     84.00 109.00   1.00    8.00    --  112.00  61.00-180.00   25
 38  ω     94.00 121.00   1.00    8.00    --  112.00  45.00  90.00   27
 39  ω     75.00 107.00   1.00    8.00    --  112.00 -94.00 120.00   32
 40  ω     39.00  83.00   1.00    8.00    --  112.00-111.00-150.00   44
 41  ω     92.00 117.00   1.00    8.00    --  112.00  30.00-150.00   25
 42  ω     88.00 115.00   1.00    8.00    --  112.00  30.00 120.00   27
 43  ω     42.00 136.00   1.00    8.00    --  112.00 -61.00 -30.00   94
 44  ω     83.00 110.00   1.00    8.00    --  112.00  61.00-150.00   27
 45  ω     48.00  94.00   1.00    8.00    --  112.00 -94.00-150.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0298805000
_diffrn_orient_matrix_UB_12      0.0336156000
_diffrn_orient_matrix_UB_13      -0.1476557000
_diffrn_orient_matrix_UB_21      0.1682787000
_diffrn_orient_matrix_UB_22      -0.0107551000
_diffrn_orient_matrix_UB_23      -0.0216529000
_diffrn_orient_matrix_UB_31      -0.0247192000
_diffrn_orient_matrix_UB_32      -0.1137572000
_diffrn_orient_matrix_UB_33      -0.0416047000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                4498
_reflns_number_total             4506
_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       'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.008(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.3882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0793
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.16102(2) 0.48482(3) 0.67759(2) 0.02007(11) Uani 1 1 d . . . . .
Cl1 Cl 0.36517(12) 0.59776(11) 0.94020(11) 0.0265(2) Uani 1 1 d . . . . .
F1 F -0.1684(4) 0.2449(5) 0.8023(4) 0.0426(11) Uani 1 1 d . . . . .
F2 F -0.2396(4) 0.1654(3) 0.6189(5) 0.0425(9) Uani 1 1 d . . . . .
F3 F -0.3352(3) 0.3124(4) 0.6645(4) 0.0354(9) Uani 1 1 d . . . . .
F4 F -0.0179(4) 0.3756(3) 0.3898(3) 0.0324(7) Uani 1 1 d . . . . .
F5 F -0.1121(5) 0.2238(3) 0.3901(4) 0.0365(8) Uani 1 1 d . . . . .
F6 F -0.2527(4) 0.3566(3) 0.4142(4) 0.0330(7) Uani 1 1 d . . . . .
O1 O -0.0816(4) 0.4167(3) 0.6475(4) 0.0219(7) Uani 1 1 d . . . . .
O2 O 0.6859(4) 0.5674(3) 0.6839(3) 0.0190(7) Uani 1 1 d . . . . .
H2 H 0.743546 0.516061 0.690247 0.028 Uiso 1 1 calc R U . . .
C1 C 0.1912(6) 0.3228(4) 0.6828(4) 0.0175(8) Uani 1 1 d . . . . .
C2 C 0.3293(5) 0.2825(4) 0.7237(4) 0.0211(9) Uani 1 1 d . . . . .
H2A H 0.408590 0.326138 0.757350 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3498(6) 0.1760(4) 0.7145(5) 0.0252(10) Uani 1 1 d . . . . .
H3 H 0.442662 0.145689 0.745130 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2339(6) 0.1147(4) 0.6603(6) 0.0276(10) Uani 1 1 d . . . . .
H4 H 0.250069 0.042863 0.648043 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0944(6) 0.1572(4) 0.6235(5) 0.0231(9) Uani 1 1 d . . . . .
H5 H 0.014932 0.113531 0.590064 0.028 Uiso 1 1 calc R U . . .
C6 C 0.0695(5) 0.2632(4) 0.6352(5) 0.0180(9) Uani 1 1 d . . . . .
C7 C -0.0827(5) 0.3174(4) 0.6031(5) 0.0189(9) Uani 1 1 d . . . . .
C8 C -0.2074(6) 0.2589(5) 0.6722(6) 0.0277(10) Uani 1 1 d . . . . .
C9 C -0.1180(6) 0.3172(4) 0.4482(5) 0.0237(10) Uani 1 1 d . . . . .
C10 C 0.3947(5) 0.5145(4) 0.6975(5) 0.0203(9) Uani 1 1 d . . . . .
H10 H 0.453775 0.492609 0.627026 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4624(5) 0.5613(4) 0.8014(4) 0.0181(8) Uani 1 1 d . . . . .
C12 C 0.6307(5) 0.5887(4) 0.8122(4) 0.0164(8) Uani 1 1 d . . . . .
C13 C 0.6557(5) 0.7044(4) 0.8478(4) 0.0165(8) Uani 1 1 d . . . . .
H13 H 0.619543 0.714071 0.939771 0.020 Uiso 1 1 calc R U . . .
C14 C 0.8241(5) 0.7263(4) 0.8600(5) 0.0235(10) Uani 1 1 d . . . . .
H14A H 0.840970 0.800219 0.881594 0.028 Uiso 1 1 calc R U . . .
H14B H 0.866810 0.711975 0.772813 0.028 Uiso 1 1 calc R U . . .
C15 C 0.9044(6) 0.6597(5) 0.9697(5) 0.0283(11) Uani 1 1 d . . . . .
H15A H 1.013326 0.674151 0.973627 0.034 Uiso 1 1 calc R U . . .
H15B H 0.867095 0.677519 1.058138 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8775(5) 0.5453(5) 0.9414(5) 0.0247(10) Uani 1 1 d . . . . .
H16 H 0.922845 0.528741 0.854859 0.030 Uiso 1 1 calc R U . . .
C17 C 0.7097(5) 0.5208(4) 0.9225(4) 0.0214(9) Uani 1 1 d . . . . .
H17A H 0.662836 0.532379 1.008468 0.026 Uiso 1 1 calc R U . . .
H17B H 0.696296 0.447100 0.897922 0.026 Uiso 1 1 calc R U . . .
C18 C 0.5646(5) 0.7807(4) 0.7546(5) 0.0201(9) Uani 1 1 d . . . . .
H18 H 0.463662 0.749093 0.733471 0.024 Uiso 1 1 calc R U . . .
C19 C 0.6320(7) 0.8025(5) 0.6211(6) 0.0373(14) Uani 1 1 d . . . . .
H19A H 0.728925 0.837233 0.637808 0.056 Uiso 1 1 calc R U . . .
H19B H 0.564076 0.847144 0.565801 0.056 Uiso 1 1 calc R U . . .
H19C H 0.646447 0.737279 0.573674 0.056 Uiso 1 1 calc R U . . .
C20 C 0.5405(9) 0.8812(5) 0.8292(7) 0.0457(16) Uani 1 1 d . . . . .
H20A H 0.488489 0.866805 0.910676 0.069 Uiso 1 1 calc R U . . .
H20B H 0.479667 0.928265 0.770999 0.069 Uiso 1 1 calc R U . . .
H20C H 0.637698 0.913302 0.854041 0.069 Uiso 1 1 calc R U . . .
C21 C 0.9537(7) 0.4764(7) 1.0502(6) 0.0407(13) Uani 1 1 d . . . . .
H21A H 1.061352 0.491570 1.058781 0.061 Uiso 1 1 calc R U . . .
H21B H 0.938491 0.403671 1.025429 0.061 Uiso 1 1 calc R U . . .
H21C H 0.910234 0.489791 1.136194 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O1 2.341(3) . ?
I1 C1 2.114(5) . ?
I1 C10 2.120(5) . ?
Cl1 C11 1.748(4) . ?
F1 C8 1.332(7) . ?
F2 C8 1.345(7) . ?
F3 C8 1.333(6) . ?
F4 C9 1.334(6) . ?
F5 C9 1.342(6) . ?
F6 C9 1.330(6) . ?
O1 C7 1.359(6) . ?
O2 H2 0.8400 . ?
O2 C12 1.428(5) . ?
C1 C2 1.376(7) . ?
C1 C6 1.390(7) . ?
C2 H2A 0.9500 . ?
C2 C3 1.393(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(7) . ?
C6 C7 1.545(6) . ?
C7 C8 1.547(7) . ?
C7 C9 1.555(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.312(7) . ?
C11 C12 1.542(6) . ?
C12 C13 1.550(7) . ?
C12 C17 1.541(6) . ?
C13 H13 1.0000 . ?
C13 C14 1.529(6) . ?
C13 C18 1.549(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.532(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.523(8) . ?
C16 H16 1.0000 . ?
C16 C17 1.533(7) . ?
C16 C21 1.528(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18 1.0000 . ?
C18 C19 1.524(7) . ?
C18 C20 1.521(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 I1 O1 75.26(17) . . ?
C1 I1 C10 93.11(19) . . ?
C10 I1 O1 168.10(15) . . ?
C7 O1 I1 112.6(3) . . ?
C12 O2 H2 109.5 . . ?
C2 C1 I1 119.6(4) . . ?
C2 C1 C6 123.8(5) . . ?
C6 C1 I1 116.5(4) . . ?
C1 C2 H2A 120.8 . . ?
C1 C2 C3 118.3(5) . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(5) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(5) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 116.6(5) . . ?
C1 C6 C7 118.5(5) . . ?
C5 C6 C7 124.9(4) . . ?
O1 C7 C6 112.0(4) . . ?
O1 C7 C8 107.9(4) . . ?
O1 C7 C9 108.8(4) . . ?
C6 C7 C8 109.7(4) . . ?
C6 C7 C9 108.8(4) . . ?
C8 C7 C9 109.7(4) . . ?
F1 C8 F2 107.3(5) . . ?
F1 C8 F3 107.1(5) . . ?
F1 C8 C7 110.5(4) . . ?
F2 C8 C7 114.0(4) . . ?
F3 C8 F2 106.5(4) . . ?
F3 C8 C7 111.1(5) . . ?
F4 C9 F5 106.0(5) . . ?
F4 C9 C7 109.6(4) . . ?
F5 C9 C7 114.7(4) . . ?
F6 C9 F4 107.1(4) . . ?
F6 C9 F5 107.2(4) . . ?
F6 C9 C7 111.8(4) . . ?
I1 C10 H10 118.1 . . ?
C11 C10 I1 123.9(3) . . ?
C11 C10 H10 118.1 . . ?
C10 C11 Cl1 121.4(4) . . ?
C10 C11 C12 123.9(4) . . ?
C12 C11 Cl1 114.7(3) . . ?
O2 C12 C11 106.7(3) . . ?
O2 C12 C13 109.8(4) . . ?
O2 C12 C17 111.0(4) . . ?
C11 C12 C13 111.3(4) . . ?
C17 C12 C11 108.5(4) . . ?
C17 C12 C13 109.6(3) . . ?
C12 C13 H13 106.3 . . ?
C14 C13 C12 108.8(4) . . ?
C14 C13 H13 106.3 . . ?
C14 C13 C18 113.9(4) . . ?
C18 C13 C12 114.6(4) . . ?
C18 C13 H13 106.3 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C13 C14 C15 111.4(4) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C14 110.7(4) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16 107.5 . . ?
C15 C16 C17 111.4(4) . . ?
C15 C16 C21 112.2(5) . . ?
C17 C16 H16 107.5 . . ?
C21 C16 H16 107.5 . . ?
C21 C16 C17 110.7(5) . . ?
C12 C17 H17A 109.3 . . ?
C12 C17 H17B 109.3 . . ?
C16 C17 C12 111.6(4) . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C13 C18 H18 107.2 . . ?
C19 C18 C13 114.8(4) . . ?
C19 C18 H18 107.2 . . ?
C20 C18 C13 109.8(4) . . ?
C20 C18 H18 107.2 . . ?
C20 C18 C19 110.2(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.84 2.09 2.890(5) 159.1 1_655 yes
C2 H2A F3 0.95 2.53 3.120(5) 120.1 1_655 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 O1 C7 C6 21.8(4) . . . . ?
I1 O1 C7 C8 142.6(3) . . . . ?
I1 O1 C7 C9 -98.4(4) . . . . ?
I1 C1 C2 C3 -174.2(3) . . . . ?
I1 C1 C6 C5 172.6(3) . . . . ?
I1 C1 C6 C7 -9.0(5) . . . . ?
I1 C10 C11 Cl1 3.7(6) . . . . ?
I1 C10 C11 C12 -176.2(3) . . . . ?
Cl1 C11 C12 O2 -171.7(3) . . . . ?
Cl1 C11 C12 C13 -52.0(4) . . . . ?
Cl1 C11 C12 C17 68.6(4) . . . . ?
O1 C7 C8 F1 -70.9(6) . . . . ?
O1 C7 C8 F2 168.2(4) . . . . ?
O1 C7 C8 F3 47.9(6) . . . . ?
O1 C7 C9 F4 56.5(5) . . . . ?
O1 C7 C9 F5 175.6(4) . . . . ?
O1 C7 C9 F6 -62.1(5) . . . . ?
O2 C12 C13 C14 -63.3(4) . . . . ?
O2 C12 C13 C18 65.5(5) . . . . ?
O2 C12 C17 C16 64.3(5) . . . . ?
C1 C2 C3 C4 2.4(7) . . . . ?
C1 C6 C7 O1 -10.0(6) . . . . ?
C1 C6 C7 C8 -129.8(5) . . . . ?
C1 C6 C7 C9 110.2(5) . . . . ?
C2 C1 C6 C5 -3.1(7) . . . . ?
C2 C1 C6 C7 175.3(4) . . . . ?
C2 C3 C4 C5 -4.4(8) . . . . ?
C3 C4 C5 C6 2.7(8) . . . . ?
C4 C5 C6 C1 1.0(7) . . . . ?
C4 C5 C6 C7 -177.2(5) . . . . ?
C5 C6 C7 O1 168.2(4) . . . . ?
C5 C6 C7 C8 48.4(6) . . . . ?
C5 C6 C7 C9 -71.5(6) . . . . ?
C6 C1 C2 C3 1.4(7) . . . . ?
C6 C7 C8 F1 51.4(6) . . . . ?
C6 C7 C8 F2 -69.5(5) . . . . ?
C6 C7 C8 F3 170.1(4) . . . . ?
C6 C7 C9 F4 -65.7(5) . . . . ?
C6 C7 C9 F5 53.3(6) . . . . ?
C6 C7 C9 F6 175.7(4) . . . . ?
C8 C7 C9 F4 174.4(4) . . . . ?
C8 C7 C9 F5 -66.6(6) . . . . ?
C8 C7 C9 F6 55.8(6) . . . . ?
C9 C7 C8 F1 170.8(5) . . . . ?
C9 C7 C8 F2 49.9(6) . . . . ?
C9 C7 C8 F3 -70.5(6) . . . . ?
C10 C11 C12 O2 8.2(6) . . . . ?
C10 C11 C12 C13 128.0(5) . . . . ?
C10 C11 C12 C17 -111.4(5) . . . . ?
C11 C12 C13 C14 178.8(4) . . . . ?
C11 C12 C13 C18 -52.4(5) . . . . ?
C11 C12 C17 C16 -178.8(4) . . . . ?
C12 C13 C14 C15 -59.8(5) . . . . ?
C12 C13 C18 C19 -80.5(6) . . . . ?
C12 C13 C18 C20 154.7(5) . . . . ?
C13 C12 C17 C16 -57.2(5) . . . . ?
C13 C14 C15 C16 57.7(6) . . . . ?
C14 C13 C18 C19 45.7(6) . . . . ?
C14 C13 C18 C20 -79.1(6) . . . . ?
C14 C15 C16 C17 -54.3(5) . . . . ?
C14 C15 C16 C21 -179.0(4) . . . . ?
C15 C16 C17 C12 55.0(5) . . . . ?
C17 C12 C13 C14 58.9(4) . . . . ?
C17 C12 C13 C18 -172.3(4) . . . . ?
C18 C13 C14 C15 171.0(4) . . . . ?
C21 C16 C17 C12 -179.5(5) . . . . ?

_olex2_date_sample_data_collection 2023-07-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.986
_oxdiff_exptl_absorpt_empirical_full_min 0.462
