#------------------------------------------------------------------------------
#$Date: 2020-07-01 02:21:11 +0300 (Wed, 01 Jul 2020) $
#$Revision: 253578 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038535.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038535
loop_
_publ_author_name
'Caspers, Lucien'
'Spils, Julian'
'Damrath, Mattis'
'Lork, Enno'
'Nachtsheim, Boris Johannes'
_publ_section_title
;
 One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic
 Iodonium Salts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01125
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H14 I, C F3 O3 S'
_chemical_formula_sum            'C20 H14 F3 I O3 S'
_chemical_formula_weight         518.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6314(4)
_cell_length_b                   19.2653(5)
_cell_length_c                   14.8884(4)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.287
_cell_volume                     3909.89(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            91480
_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         36.414
_diffrn_reflns_theta_min         2.285
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.5411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1395 before and 0.0510 after correction. The Ratio of minimum to maximum transmission is 0.7243. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.075
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.391(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         19037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0266
_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)+(0.0181P)²+2.2376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0530
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                16821
_reflns_number_total             19037
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01125_si_002.cif
_cod_data_source_block           damrathm180702_a
_cod_database_code               4038535
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.775
_shelx_estimated_absorpt_t_min   0.716
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.609(10)
 0.391(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9), C29(H29)
3.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8),
 C11(H11), C11'(H11'), C12(H12), C12'(H12'), C13(H13), C21(H21), C22(H22),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C31(H31), C31'(H31'),
 C32(H32), C32'(H32'), C33(H33)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.29558(2) 0.25302(2) 0.52265(2) 0.01097(3) Uani 1 1 d . . . . .
I002 I 0.40156(2) 0.25429(2) 0.86133(2) 0.01430(3) Uani 1 1 d . . . . .
S21 S 0.26038(5) 0.39498(3) 0.69177(5) 0.01781(12) Uani 1 1 d . . . . .
F21 F 0.2893(2) 0.52331(10) 0.64148(17) 0.0510(6) Uani 1 1 d . . . . .
F22 F 0.4084(2) 0.45481(14) 0.61207(18) 0.0561(7) Uani 1 1 d . . . . .
F23 F 0.38307(18) 0.48957(11) 0.74789(15) 0.0428(6) Uani 1 1 d . . . . .
O21 O 0.3285(2) 0.34326(11) 0.72454(16) 0.0325(5) Uani 1 1 d . . . . .
O22 O 0.19035(18) 0.41912(12) 0.75687(16) 0.0311(5) Uani 1 1 d . . . . .
O23 O 0.22019(16) 0.37958(10) 0.60405(14) 0.0245(4) Uani 1 1 d . . . . .
C0AA C 0.4018(2) 0.11908(13) 0.9635(2) 0.0235(5) Uani 1 1 d . . . . .
H0AA H 0.353329 0.106665 0.920490 0.028 Uiso 1 1 calc R . . . .
C1 C 0.4525(2) 0.12007(14) 0.33917(18) 0.0197(5) Uani 1 1 d . . . . .
H1 H 0.511869 0.122203 0.305898 0.024 Uiso 1 1 calc R . . . .
C2 C 0.3903(2) 0.06355(14) 0.32879(19) 0.0225(5) Uani 1 1 d . . . . .
H2 H 0.407294 0.027781 0.287713 0.027 Uiso 1 1 calc R . . . .
C3 C 0.3042(2) 0.05845(13) 0.37718(18) 0.0210(5) Uani 1 1 d . . . . .
H3 H 0.263906 0.018465 0.371405 0.025 Uiso 1 1 calc R . . . .
C4 C 0.2767(2) 0.11195(12) 0.43429(18) 0.0170(5) Uani 1 1 d . . . . .
H4 H 0.216892 0.109910 0.466928 0.020 Uiso 1 1 calc R . . . .
C4A C 0.33897(19) 0.16841(12) 0.44232(18) 0.0138(4) Uani 1 1 d . . . . .
C5 C 0.3090(2) 0.38359(12) 0.40893(18) 0.0192(5) Uani 1 1 d . . . . .
H5 H 0.249112 0.395366 0.437766 0.023 Uiso 1 1 calc R . . . .
C5A C 0.3572(2) 0.32215(12) 0.42860(17) 0.0144(5) Uani 1 1 d . . . . .
C6 C 0.3511(3) 0.42739(14) 0.3457(2) 0.0258(6) Uani 1 1 d . . . . .
H6 H 0.319931 0.470016 0.330999 0.031 Uiso 1 1 calc R . . . .
C7 C 0.4377(3) 0.40934(15) 0.3043(2) 0.0269(6) Uani 1 1 d . . . . .
H7 H 0.465443 0.439610 0.260849 0.032 Uiso 1 1 calc R . . . .
C8 C 0.4854(2) 0.34718(15) 0.32525(18) 0.0226(5) Uani 1 1 d . . . . .
H8 H 0.545002 0.335435 0.295806 0.027 Uiso 1 1 calc R . . . .
C8A C 0.44576(19) 0.30237(13) 0.38931(17) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.49612(17) 0.23477(12) 0.41449(15) 0.0154(4) Uani 1 1 d . . . . .
H9 H 0.554572 0.229098 0.374573 0.019 Uiso 1 1 calc R . . . .
C9A C 0.42836(19) 0.17391(13) 0.39825(17) 0.0148(4) Uani 1 1 d . . . . .
C10 C 0.53247(17) 0.23551(13) 0.51230(16) 0.0175(5) Uani 1 1 d . . . . .
C11 C 0.5500(2) 0.17266(16) 0.55635(19) 0.0205(5) Uani 1 1 d . . . . .
H11 H 0.539320 0.130062 0.525722 0.025 Uiso 1 1 calc R . . . .
C11' C 0.5492(2) 0.29738(16) 0.5578(2) 0.0211(5) Uani 1 1 d . . . . .
H11' H 0.538033 0.340441 0.528422 0.025 Uiso 1 1 calc R . . . .
C12 C 0.5831(2) 0.17207(18) 0.6450(2) 0.0255(6) Uani 1 1 d . . . . .
H12 H 0.594542 0.129180 0.674713 0.031 Uiso 1 1 calc R . . . .
C12' C 0.5825(2) 0.29649(18) 0.6466(2) 0.0261(6) Uani 1 1 d . . . . .
H12' H 0.593514 0.338937 0.677468 0.031 Uiso 1 1 calc R . . . .
C13 C 0.59941(19) 0.23403(18) 0.68970(18) 0.0290(7) Uani 1 1 d . . . . .
H13 H 0.622194 0.233651 0.750000 0.035 Uiso 1 1 calc R . . . .
C21 C 0.5142(2) 0.39470(14) 1.06278(19) 0.0212(5) Uani 1 1 d . . . . .
H21 H 0.565046 0.395221 1.106447 0.025 Uiso 1 1 calc R . . . .
C22 C 0.4523(2) 0.45194(15) 1.0543(2) 0.0254(6) Uani 1 1 d . . . . .
H22 H 0.462195 0.491162 1.091900 0.030 Uiso 1 1 calc R . . . .
C23 C 0.3767(2) 0.45280(14) 0.99237(19) 0.0235(5) Uani 1 1 d . . . . .
H23 H 0.334922 0.492100 0.987852 0.028 Uiso 1 1 calc R . . . .
C24 C 0.3623(2) 0.39573(13) 0.93672(17) 0.0174(4) Uani 1 1 d . . . . .
H24 H 0.310768 0.395051 0.893812 0.021 Uiso 1 1 calc R . . . .
C24A C 0.42582(19) 0.33969(13) 0.94587(17) 0.0152(4) Uani 1 1 d . . . . .
C25A C 0.4451(2) 0.18434(13) 0.96292(18) 0.0180(5) Uani 1 1 d . . . . .
C26 C 0.4320(2) 0.07265(15) 1.0293(2) 0.0299(7) Uani 1 1 d . . . . .
H26 H 0.404779 0.027289 1.031204 0.036 Uiso 1 1 calc R . . . .
C27 C 0.5016(3) 0.09207(16) 1.0922(2) 0.0298(7) Uani 1 1 d . . . . .
H27 H 0.521678 0.059869 1.136902 0.036 Uiso 1 1 calc R . . . .
C28 C 0.5422(2) 0.15798(15) 1.09071(19) 0.0233(5) Uani 1 1 d . . . . .
H28 H 0.588194 0.170963 1.135599 0.028 Uiso 1 1 calc R . . . .
C28A C 0.51619(18) 0.20589(13) 1.02358(18) 0.0175(4) Uani 1 1 d . . . . .
C29 C 0.56990(18) 0.27460(13) 1.01745(17) 0.0166(4) Uani 1 1 d . . . . .
H29 H 0.604558 0.280700 1.076117 0.020 Uiso 1 1 calc R . . . .
C29A C 0.50233(18) 0.33663(13) 1.00767(16) 0.0160(4) Uani 1 1 d . . . . .
C30 C 0.65099(18) 0.27083(13) 0.94483(16) 0.0164(4) Uani 1 1 d . . . . .
C31 C 0.6817(2) 0.33019(14) 0.89960(19) 0.0218(5) Uani 1 1 d . . . . .
H31 H 0.648846 0.373027 0.909389 0.026 Uiso 1 1 calc R . . . .
C31' C 0.7000(2) 0.20867(15) 0.92848(18) 0.0217(5) Uani 1 1 d . . . . .
H31' H 0.679292 0.167521 0.958110 0.026 Uiso 1 1 calc R . . . .
C32 C 0.7607(2) 0.32703(16) 0.8398(2) 0.0255(6) Uani 1 1 d . . . . .
H32 H 0.781055 0.367786 0.809094 0.031 Uiso 1 1 calc R . . . .
C32' C 0.7791(2) 0.20614(15) 0.86904(19) 0.0231(5) Uani 1 1 d . . . . .
H32' H 0.812271 0.163481 0.858974 0.028 Uiso 1 1 calc R . . . .
C33 C 0.80926(19) 0.26525(15) 0.82493(17) 0.0225(5) Uani 1 1 d . . . . .
H33 H 0.863160 0.263501 0.784545 0.027 Uiso 1 1 calc R . . . .
C34 C 0.3393(3) 0.46985(17) 0.6722(2) 0.0275(7) Uani 1 1 d . . . . .
S1 S 0.27525(5) 0.11411(3) 0.71355(5) 0.01884(13) Uani 1 1 d . . . . .
F1 F 0.24910(18) -0.00450(11) 0.63290(19) 0.0481(6) Uani 1 1 d . . . . .
F2 F 0.36354(17) -0.00590(10) 0.73195(15) 0.0380(5) Uani 1 1 d . . . . .
F3 F 0.38908(18) 0.04323(10) 0.60488(14) 0.0342(5) Uani 1 1 d . . . . .
O1 O 0.36473(18) 0.14722(12) 0.74416(18) 0.0361(6) Uani 1 1 d . . . . .
O2 O 0.20918(18) 0.09410(11) 0.78376(15) 0.0306(5) Uani 1 1 d . . . . .
O3 O 0.22976(17) 0.14699(10) 0.63718(15) 0.0267(4) Uani 1 1 d . . . . .
C14 C 0.3225(3) 0.03262(15) 0.6683(2) 0.0240(6) Uani 1 1 d . . . . .
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'
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'
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
C4A I1 C5A 89.99(10) . . ?
C24A I002 C25A 91.51(11) . . ?
O21 S21 C34 102.70(16) . . ?
O22 S21 O21 114.94(15) . . ?
O22 S21 O23 115.05(14) . . ?
O22 S21 C34 104.10(15) . . ?
O23 S21 O21 113.97(13) . . ?
O23 S21 C34 103.98(14) . . ?
C25A C0AA H0AA 121.3 . . ?
C25A C0AA C26 117.4(3) . . ?
C26 C0AA H0AA 121.3 . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C9A 120.5(3) . . ?
C9A C1 H1 119.7 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 121.0 . . ?
C4A C4 C3 118.1(3) . . ?
C4A C4 H4 121.0 . . ?
C4 C4A I1 118.99(19) . . ?
C4 C4A C9A 123.9(2) . . ?
C9A C4A I1 117.12(18) . . ?
C5A C5 H5 121.1 . . ?
C5A C5 C6 117.9(3) . . ?
C6 C5 H5 121.1 . . ?
C5 C5A I1 119.5(2) . . ?
C5 C5A C8A 123.7(2) . . ?
C8A C5A I1 116.82(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.9 . . ?
C8A C8 C7 120.1(3) . . ?
C8A C8 H8 119.9 . . ?
C5A C8A C8 116.9(2) . . ?
C5A C8A C9 121.5(2) . . ?
C8 C8A C9 121.6(2) . . ?
C8A C9 H9 107.9 . . ?
C8A C9 C10 111.8(2) . . ?
C9A C9 C8A 110.44(19) . . ?
C9A C9 H9 107.9 . . ?
C9A C9 C10 110.8(2) . . ?
C10 C9 H9 107.9 . . ?
C1 C9A C9 122.1(2) . . ?
C4A C9A C1 116.5(2) . . ?
C4A C9A C9 121.3(2) . . ?
C11 C10 C9 119.4(2) . . ?
C11' C10 C9 121.5(2) . . ?
C11' C10 C11 119.1(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11' H11' 119.9 . . ?
C10 C11' C12' 120.2(3) . . ?
C12' C11' H11' 119.9 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11' C12' H12' 119.9 . . ?
C13 C12' C11' 120.2(3) . . ?
C13 C12' H12' 119.9 . . ?
C12 C13 H13 120.0 . . ?
C12' C13 C12 120.0(3) . . ?
C12' C13 H13 120.0 . . ?
C22 C21 H21 119.7 . . ?
C22 C21 C29A 120.7(3) . . ?
C29A C21 H21 119.7 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.5(3) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 121.1 . . ?
C24A C24 C23 117.9(2) . . ?
C24A C24 H24 121.1 . . ?
C24 C24A I002 116.88(18) . . ?
C24 C24A C29A 124.3(2) . . ?
C29A C24A I002 118.78(18) . . ?
C0AA C25A I002 117.5(2) . . ?
C28A C25A I002 118.14(18) . . ?
C28A C25A C0AA 124.3(2) . . ?
C0AA C26 H26 119.8 . . ?
C27 C26 C0AA 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.7(3) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.6 . . ?
C27 C28 C28A 120.8(3) . . ?
C28A C28 H28 119.6 . . ?
C25A C28A C28 116.2(2) . . ?
C25A C28A C29 124.0(2) . . ?
C28 C28A C29 119.6(2) . . ?
C28A C29 H29 106.2 . . ?
C28A C29 C29A 113.6(2) . . ?
C28A C29 C30 110.3(2) . . ?
C29A C29 H29 106.2 . . ?
C29A C29 C30 113.8(2) . . ?
C30 C29 H29 106.2 . . ?
C21 C29A C29 120.3(2) . . ?
C24A C29A C21 116.2(2) . . ?
C24A C29A C29 123.5(2) . . ?
C31 C30 C29 120.9(2) . . ?
C31 C30 C31' 118.6(2) . . ?
C31' C30 C29 120.3(2) . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31' H31' 119.6 . . ?
C30 C31' C32' 120.7(2) . . ?
C32' C31' H31' 119.6 . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.6(3) . . ?
C33 C32 H32 119.7 . . ?
C31' C32' H32' 119.9 . . ?
C33 C32' C31' 120.3(3) . . ?
C33 C32' H32' 119.9 . . ?
C32 C33 H33 120.2 . . ?
C32' C33 C32 119.6(2) . . ?
C32' C33 H33 120.2 . . ?
F21 C34 S21 111.6(3) . . ?
F21 C34 F22 107.6(3) . . ?
F21 C34 F23 107.6(3) . . ?
F22 C34 S21 110.7(2) . . ?
F23 C34 S21 110.8(2) . . ?
F23 C34 F22 108.3(3) . . ?
O1 S1 C14 101.41(15) . . ?
O2 S1 O1 114.70(16) . . ?
O2 S1 O3 115.05(14) . . ?
O2 S1 C14 105.05(14) . . ?
O3 S1 O1 114.61(15) . . ?
O3 S1 C14 103.79(14) . . ?
F1 C14 S1 110.0(2) . . ?
F2 C14 S1 111.4(2) . . ?
F2 C14 F1 107.3(3) . . ?
F3 C14 S1 111.8(2) . . ?
F3 C14 F1 108.3(3) . . ?
F3 C14 F2 107.8(3) . . ?
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 C4A 2.106(2) . ?
I1 C5A 2.107(3) . ?
I002 C24A 2.098(2) . ?
I002 C25A 2.111(3) . ?
S21 O21 1.447(2) . ?
S21 O22 1.438(2) . ?
S21 O23 1.447(2) . ?
S21 C34 1.823(3) . ?
F21 C34 1.317(4) . ?
F22 C34 1.332(4) . ?
F23 C34 1.330(4) . ?
C0AA H0AA 0.9500 . ?
C0AA C25A 1.389(4) . ?
C0AA C26 1.390(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(4) . ?
C1 C9A 1.399(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C4A 1.385(4) . ?
C4A C9A 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C5A 1.385(3) . ?
C5 C6 1.388(4) . ?
C5A C8A 1.395(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.398(4) . ?
C8 H8 0.9500 . ?
C8 C8A 1.396(4) . ?
C8A C9 1.519(3) . ?
C9 H9 1.0000 . ?
C9 C9A 1.512(3) . ?
C9 C10 1.538(3) . ?
C10 C11 1.398(4) . ?
C10 C11' 1.390(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(4) . ?
C11' H11' 0.9500 . ?
C11' C12' 1.398(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(5) . ?
C12' H12' 0.9500 . ?
C12' C13 1.383(5) . ?
C13 H13 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.395(4) . ?
C21 C29A 1.397(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(4) . ?
C24 H24 0.9500 . ?
C24 C24A 1.390(4) . ?
C24A C29A 1.392(4) . ?
C25A C28A 1.388(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(4) . ?
C28 H28 0.9500 . ?
C28 C28A 1.406(4) . ?
C28A C29 1.515(4) . ?
C29 H29 1.0000 . ?
C29 C29A 1.516(3) . ?
C29 C30 1.548(3) . ?
C30 C31 1.391(4) . ?
C30 C31' 1.392(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.399(4) . ?
C31' H31' 0.9500 . ?
C31' C32' 1.396(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.380(4) . ?
C32' H32' 0.9500 . ?
C32' C33 1.377(4) . ?
C33 H33 0.9500 . ?
S1 O1 1.450(2) . ?
S1 O2 1.433(2) . ?
S1 O3 1.442(2) . ?
S1 C14 1.826(3) . ?
F1 C14 1.337(4) . ?
F2 C14 1.328(4) . ?
F3 C14 1.326(4) . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.609(10)
2 0.391(10)
