#------------------------------------------------------------------------------
#$Date: 2023-10-06 03:48:18 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159569.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_7159569
loop_
_publ_author_name
'Yu, Shi-Wei'
'Chen, Zu-Jia'
'Chen, Zhao-Hua'
'Chen, Si-Hong'
'Yang, Kai'
'Xu, Wen-Jin'
'Wang, Zhao-Yang'
_publ_section_title
;
 Trace water in a BF₃·OEt₂ system: a facile
 access to sulfinyl alkenylsulfones from alkynes and sodium sulfinates.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7776
_journal_page_last               7781
_journal_paper_doi               10.1039/d3ob01249b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C22 H19 F O3 S2'
_chemical_formula_sum            'C22 H19 F O3 S2'
_chemical_formula_weight         414.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-11-04 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                101.895(6)
_cell_angle_beta                 92.033(7)
_cell_angle_gamma                91.343(7)
_cell_formula_units_Z            4
_cell_length_a                   8.4367(9)
_cell_length_b                   10.2011(7)
_cell_length_c                   24.4853(15)
_cell_measurement_reflns_used    3364
_cell_measurement_temperature    297
_cell_measurement_theta_max      25.1900
_cell_measurement_theta_min      2.3110
_cell_volume                     2059.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  41.60   0.90    5.00    --   15.65 -77.00 -90.00  104
  2  ω    -25.00  22.70   0.90    5.00    --  -16.43 -99.00-180.00   53
  3  ω     -2.00  70.00   0.90    5.00    --   15.65  38.00-180.00   80
  4  ω    -10.00  80.00   0.90    5.00    --   15.65  77.00  30.00  100
  5  ω     49.00  75.10   0.90    5.00    --   15.65 178.00 -30.00   29
  6  ω    -86.00 -32.00   0.90    5.00    --  -16.43 -38.00 -60.00   60
  7  ω     -6.00  26.40   0.90    5.00    --   15.65 -57.00 150.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0388002000
_diffrn_orient_matrix_UB_12      -0.0212284000
_diffrn_orient_matrix_UB_13      -0.0254005000
_diffrn_orient_matrix_UB_21      0.0694974000
_diffrn_orient_matrix_UB_22      0.0369630000
_diffrn_orient_matrix_UB_23      0.0119029000
_diffrn_orient_matrix_UB_31      0.0273652000
_diffrn_orient_matrix_UB_32      -0.0568971000
_diffrn_orient_matrix_UB_33      0.0095410000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16406
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.041
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0614
_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)+(0.0432P)²+0.4433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4818
_reflns_number_total             7242
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01249b2.cif
_cod_data_source_block           exp_12199
_cod_depositor_comments
'Adding full bibliography for 7159568--7159569.cif.'
_cod_database_code               7159569
_shelx_shelxl_version_number     2019/2
_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.
;
_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:
 C10(H10), C12(H12), C14(H14), C16(H16), C18(H18), C22(H22), C24(H24),
 C26(H26), C28(H28), C30(H30), C32(H32), C38(H38), C44(H44), C5(H5), C7(H7),
 C13(H13), C15(H15), C17(H17), C19(H19), C27(H27), C29(H29), C33(H33), C35(H35),
  C39(H39), C41(H41), C43(H43)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C9(H9A,H9B,H9C), C37(H37A,H37B,H37C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.800
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.01161(10) 0.38497(8) 0.55331(3) 0.0472(2) Uani 1 1 d . . . . .
S4 S 0.39976(12) 0.68441(9) 0.57107(3) 0.0555(3) Uani 1 1 d . . . . .
F1 F -0.1491(3) 0.8062(2) 0.77277(8) 0.0994(8) Uani 1 1 d . . . . .
O1 O 0.5529(3) 0.6258(3) 0.56244(10) 0.0719(8) Uani 1 1 d . . . . .
O4 O 0.3688(4) 0.7674(3) 0.62365(9) 0.0853(9) Uani 1 1 d . . . . .
O6 O 0.0995(3) 0.3072(2) 0.50697(8) 0.0670(7) Uani 1 1 d . . . . .
C1 C 0.0647(4) 0.6153(3) 0.63301(11) 0.0385(7) Uani 1 1 d . . . . .
C4 C 0.1336(4) 0.5339(3) 0.58318(11) 0.0374(7) Uani 1 1 d . . . . .
C6 C 0.0335(4) 0.3059(3) 0.61196(12) 0.0446(8) Uani 1 1 d . . . . .
C8 C 0.3612(4) 0.7761(3) 0.51921(13) 0.0476(8) Uani 1 1 d . . . . .
C10 C 0.2606(4) 0.5505(3) 0.55520(11) 0.0432(8) Uani 1 1 d . . . . .
H10 H 0.278044 0.484408 0.523839 0.052 Uiso 1 1 calc R U . . .
C12 C -0.0799(4) 0.6705(3) 0.62867(13) 0.0517(9) Uani 1 1 d . . . . .
H12 H -0.129497 0.664005 0.593649 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1371(4) 0.6228(3) 0.68553(12) 0.0525(9) Uani 1 1 d . . . . .
H14 H 0.235248 0.584942 0.688866 0.063 Uiso 1 1 calc R U . . .
C16 C 0.0629(5) 0.6867(4) 0.73282(13) 0.0615(10) Uani 1 1 d . . . . .
H16 H 0.109135 0.691072 0.768236 0.074 Uiso 1 1 calc R U . . .
C18 C -0.0702(5) 0.3312(3) 0.65417(14) 0.0615(10) Uani 1 1 d . . . . .
H18 H -0.150853 0.391409 0.653214 0.074 Uiso 1 1 calc R U . . .
C20 C -0.0773(5) 0.7420(4) 0.72626(14) 0.0622(10) Uani 1 1 d . . . . .
C22 C -0.1535(5) 0.7360(4) 0.67583(14) 0.0661(11) Uani 1 1 d . . . . .
H22 H -0.251526 0.774497 0.673134 0.079 Uiso 1 1 calc R U . . .
C24 C 0.4384(5) 0.7492(5) 0.47080(17) 0.0837(14) Uani 1 1 d . . . . .
H24 H 0.509293 0.679709 0.464446 0.100 Uiso 1 1 calc R U . . .
C26 C 0.1635(6) 0.1524(4) 0.6572(2) 0.0862(14) Uani 1 1 d . . . . .
H26 H 0.243287 0.091265 0.657880 0.103 Uiso 1 1 calc R U . . .
C28 C 0.2559(6) 0.8761(4) 0.52724(18) 0.0832(13) Uani 1 1 d . . . . .
H28 H 0.200619 0.894298 0.560003 0.100 Uiso 1 1 calc R U . . .
C30 C 0.2309(7) 0.9504(4) 0.4872(3) 0.1021(17) Uani 1 1 d . . . . .
H30 H 0.157995 1.018331 0.493105 0.123 Uiso 1 1 calc R U . . .
C32 C 0.4119(6) 0.8249(5) 0.43092(19) 0.0992(17) Uani 1 1 d . . . . .
H32 H 0.464938 0.805517 0.397692 0.119 Uiso 1 1 calc R U . . .
C34 C 0.2804(7) 1.0136(5) 0.3964(2) 0.138(2) Uani 1 1 d . . . . .
H34A H 0.171139 1.003274 0.383488 0.207 Uiso 1 1 calc R U . . .
H34B H 0.347167 0.986272 0.365455 0.207 Uiso 1 1 calc R U . . .
H34C H 0.304017 1.105803 0.413379 0.207 Uiso 1 1 calc R U . . .
C36 C 0.0744(7) 0.1031(5) 0.74833(19) 0.136(2) Uani 1 1 d . . . . .
H36A H 0.057372 0.008676 0.734129 0.204 Uiso 1 1 calc R U . . .
H36B H -0.004205 0.134596 0.774945 0.204 Uiso 1 1 calc R U . . .
H36C H 0.178157 0.119604 0.766167 0.204 Uiso 1 1 calc R U . . .
C38 C 0.1504(5) 0.2165(4) 0.61296(15) 0.0669(10) Uani 1 1 d . . . . .
H38 H 0.220698 0.198878 0.584110 0.080 Uiso 1 1 calc R U . . .
C40 C 0.0613(6) 0.1766(4) 0.70048(18) 0.0795(14) Uani 1 1 d . . . . .
C42 C 0.3101(6) 0.9268(5) 0.4393(2) 0.0844(15) Uani 1 1 d . . . . .
C44 C -0.0543(6) 0.2666(4) 0.69833(15) 0.0788(13) Uani 1 1 d . . . . .
H44 H -0.124178 0.284918 0.727260 0.095 Uiso 1 1 calc R U . . .
S2 S 0.49393(11) 0.35009(8) 0.94792(3) 0.0494(2) Uani 1 1 d . . . . .
S3 S 0.09700(12) 0.60458(9) 0.92394(3) 0.0553(3) Uani 1 1 d . . . . .
F2 F 0.6232(4) 0.4964(3) 0.71343(10) 0.1286(11) Uani 1 1 d . . . . .
O2 O -0.0556(3) 0.5498(3) 0.93402(10) 0.0745(7) Uani 1 1 d . . . . .
O3 O 0.4070(3) 0.3192(2) 0.99557(8) 0.0639(7) Uani 1 1 d . . . . .
O5 O 0.1264(3) 0.6315(3) 0.87047(9) 0.0784(8) Uani 1 1 d . . . . .
C2 C 0.4614(5) -0.0207(4) 0.80768(15) 0.0635(10) Uani 1 1 d . . . . .
C3 C 0.1371(4) 0.7523(3) 0.97411(12) 0.0454(8) Uani 1 1 d . . . . .
C5 C 0.0507(5) 0.7828(4) 1.02069(14) 0.0692(11) Uani 1 1 d . . . . .
H5 H -0.029437 0.724162 1.026961 0.083 Uiso 1 1 calc R U . . .
C7 C 0.5956(4) 0.1842(3) 0.85403(14) 0.0584(9) Uani 1 1 d . . . . .
H7 H 0.680968 0.244754 0.856566 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2290(6) 1.1233(4) 1.09073(15) 0.0886(14) Uani 1 1 d . . . . .
H9A H 0.322983 1.117185 1.113255 0.133 Uiso 1 1 calc R U . . .
H9B H 0.140785 1.143936 1.114372 0.133 Uiso 1 1 calc R U . . .
H9C H 0.244554 1.192786 1.070130 0.133 Uiso 1 1 calc R U . . .
C11 C 0.4280(4) 0.4753(3) 0.86130(12) 0.0431(8) Uani 1 1 d . . . . .
C13 C 0.2387(4) 0.4956(3) 0.94158(12) 0.0459(8) Uani 1 1 d . . . . .
H13 H 0.222657 0.463953 0.974030 0.055 Uiso 1 1 calc R U . . .
C15 C 0.5766(5) 0.5329(3) 0.86076(15) 0.0592(10) Uani 1 1 d . . . . .
H15 H 0.632417 0.566634 0.894347 0.071 Uiso 1 1 calc R U . . .
C17 C 0.6434(5) 0.5414(4) 0.81154(19) 0.0796(12) Uani 1 1 d . . . . .
H17 H 0.743633 0.580997 0.811246 0.096 Uiso 1 1 calc R U . . .
C19 C 0.5835(5) 0.0714(4) 0.81152(14) 0.0682(11) Uani 1 1 d . . . . .
H19 H 0.660503 0.057952 0.784850 0.082 Uiso 1 1 calc R U . . .
C21 C 0.5597(7) 0.4904(4) 0.76290(17) 0.0770(13) Uani 1 1 d . . . . .
C23 C 0.4798(4) 0.2052(3) 0.89230(11) 0.0401(7) Uani 1 1 d . . . . .
C25 C 0.3650(4) 0.4537(3) 0.91403(12) 0.0410(8) Uani 1 1 d . . . . .
C27 C 0.3446(4) 0.4245(3) 0.81106(12) 0.0523(9) Uani 1 1 d . . . . .
H27 H 0.243619 0.385921 0.811033 0.063 Uiso 1 1 calc R U . . .
C29 C 0.3567(4) 0.1151(3) 0.88925(13) 0.0563(9) Uani 1 1 d . . . . .
H29 H 0.278576 0.129481 0.915517 0.068 Uiso 1 1 calc R U . . .
C31 C 0.1958(5) 0.9913(3) 1.05053(15) 0.0561(9) Uani 1 1 d . . . . .
C33 C 0.3486(5) 0.0028(4) 0.84711(15) 0.0654(10) Uani 1 1 d . . . . .
H33 H 0.264496 -0.058700 0.845305 0.079 Uiso 1 1 calc R U . . .
C35 C 0.2819(5) 0.9586(4) 1.00411(17) 0.0734(12) Uani 1 1 d . . . . .
H35 H 0.361451 1.017923 0.997962 0.088 Uiso 1 1 calc R U . . .
C37 C 0.4538(6) -0.1452(5) 0.76152(18) 0.1131(18) Uani 1 1 d . . . . .
H37A H 0.444718 -0.223270 0.777516 0.170 Uiso 1 1 calc R U . . .
H37B H 0.548654 -0.148974 0.740792 0.170 Uiso 1 1 calc R U . . .
H37C H 0.363247 -0.142220 0.736981 0.170 Uiso 1 1 calc R U . . .
C39 C 0.2545(5) 0.8403(4) 0.96598(15) 0.0690(11) Uani 1 1 d . . . . .
H39 H 0.315742 0.820035 0.934680 0.083 Uiso 1 1 calc R U . . .
C41 C 0.4125(6) 0.4315(4) 0.76138(14) 0.0685(12) Uani 1 1 d . . . . .
H41 H 0.358928 0.396761 0.727440 0.082 Uiso 1 1 calc R U . . .
C43 C 0.0831(5) 0.9014(4) 1.05851(15) 0.0742(12) Uani 1 1 d . . . . .
H43 H 0.025349 0.920368 1.090690 0.089 Uiso 1 1 calc R U . . .
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'
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
O6 S1 C4 106.90(14) . . ?
O6 S1 C6 108.05(15) . . ?
C6 S1 C4 96.27(13) . . ?
O1 S4 C8 108.60(16) . . ?
O1 S4 C10 105.89(16) . . ?
O4 S4 O1 119.52(17) . . ?
O4 S4 C8 107.97(17) . . ?
O4 S4 C10 110.05(15) . . ?
C8 S4 C10 103.69(14) . . ?
C12 C1 C4 120.0(3) . . ?
C12 C1 C14 119.5(3) . . ?
C14 C1 C4 120.1(3) . . ?
C1 C4 S1 112.4(2) . . ?
C10 C4 S1 114.7(2) . . ?
C10 C4 C1 132.9(3) . . ?
C18 C6 S1 120.2(3) . . ?
C38 C6 S1 119.4(3) . . ?
C38 C6 C18 120.3(3) . . ?
C24 C8 S4 120.2(3) . . ?
C24 C8 C28 119.2(4) . . ?
C28 C8 S4 120.7(3) . . ?
S4 C10 H10 116.7 . . ?
C4 C10 S4 126.6(3) . . ?
C4 C10 H10 116.7 . . ?
C1 C12 H12 119.6 . . ?
C1 C12 C22 120.7(3) . . ?
C22 C12 H12 119.6 . . ?
C1 C14 H14 120.0 . . ?
C16 C14 C1 119.9(3) . . ?
C16 C14 H14 120.0 . . ?
C14 C16 H16 120.9 . . ?
C20 C16 C14 118.3(3) . . ?
C20 C16 H16 120.9 . . ?
C6 C18 H18 120.3 . . ?
C6 C18 C44 119.4(4) . . ?
C44 C18 H18 120.3 . . ?
C16 C20 F1 118.2(3) . . ?
C16 C20 C22 123.9(3) . . ?
C22 C20 F1 117.9(4) . . ?
C12 C22 H22 121.2 . . ?
C20 C22 C12 117.6(4) . . ?
C20 C22 H22 121.2 . . ?
C8 C24 H24 120.0 . . ?
C8 C24 C32 119.9(4) . . ?
C32 C24 H24 120.0 . . ?
C38 C26 H26 119.2 . . ?
C40 C26 H26 119.2 . . ?
C40 C26 C38 121.6(4) . . ?
C8 C28 H28 119.9 . . ?
C8 C28 C30 120.2(4) . . ?
C30 C28 H28 119.9 . . ?
C28 C30 H30 119.4 . . ?
C42 C30 C28 121.3(5) . . ?
C42 C30 H30 119.4 . . ?
C24 C32 H32 119.5 . . ?
C42 C32 C24 121.1(4) . . ?
C42 C32 H32 119.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C42 C34 H34A 109.5 . . ?
C42 C34 H34B 109.5 . . ?
C42 C34 H34C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C40 C36 H36A 109.5 . . ?
C40 C36 H36B 109.5 . . ?
C40 C36 H36C 109.5 . . ?
C6 C38 C26 119.3(4) . . ?
C6 C38 H38 120.4 . . ?
C26 C38 H38 120.4 . . ?
C26 C40 C36 121.1(5) . . ?
C44 C40 C26 117.8(4) . . ?
C44 C40 C36 121.0(5) . . ?
C30 C42 C32 118.3(4) . . ?
C30 C42 C34 119.4(6) . . ?
C32 C42 C34 122.3(6) . . ?
C18 C44 H44 119.2 . . ?
C40 C44 C18 121.6(4) . . ?
C40 C44 H44 119.2 . . ?
O3 S2 C23 108.10(14) . . ?
O3 S2 C25 106.68(15) . . ?
C23 S2 C25 96.11(13) . . ?
O2 S3 C3 108.62(16) . . ?
O2 S3 C13 106.38(16) . . ?
O5 S3 O2 119.59(16) . . ?
O5 S3 C3 108.22(16) . . ?
O5 S3 C13 109.92(16) . . ?
C13 S3 C3 102.83(15) . . ?
C19 C2 C33 117.8(3) . . ?
C19 C2 C37 120.5(4) . . ?
C33 C2 C37 121.8(4) . . ?
C5 C3 S3 121.1(3) . . ?
C5 C3 C39 119.1(3) . . ?
C39 C3 S3 119.9(3) . . ?
C3 C5 H5 120.3 . . ?
C3 C5 C43 119.4(4) . . ?
C43 C5 H5 120.3 . . ?
C19 C7 H7 120.6 . . ?
C23 C7 H7 120.6 . . ?
C23 C7 C19 118.9(4) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C31 C9 H9A 109.5 . . ?
C31 C9 H9B 109.5 . . ?
C31 C9 H9C 109.5 . . ?
C15 C11 C25 120.2(3) . . ?
C15 C11 C27 119.6(3) . . ?
C27 C11 C25 119.9(3) . . ?
S3 C13 H13 116.4 . . ?
C25 C13 S3 127.2(2) . . ?
C25 C13 H13 116.4 . . ?
C11 C15 H15 119.6 . . ?
C17 C15 C11 120.9(3) . . ?
C17 C15 H15 119.6 . . ?
C15 C17 H17 120.8 . . ?
C21 C17 C15 118.5(4) . . ?
C21 C17 H17 120.8 . . ?
C2 C19 C7 121.7(4) . . ?
C2 C19 H19 119.2 . . ?
C7 C19 H19 119.2 . . ?
F2 C21 C17 119.8(5) . . ?
F2 C21 C41 117.5(4) . . ?
C17 C21 C41 122.7(3) . . ?
C7 C23 S2 119.6(3) . . ?
C29 C23 S2 119.9(2) . . ?
C29 C23 C7 120.5(3) . . ?
C11 C25 S2 111.9(2) . . ?
C13 C25 S2 114.9(2) . . ?
C13 C25 C11 133.2(3) . . ?
C11 C27 H27 120.2 . . ?
C41 C27 C11 119.6(4) . . ?
C41 C27 H27 120.2 . . ?
C23 C29 H29 120.2 . . ?
C23 C29 C33 119.5(3) . . ?
C33 C29 H29 120.2 . . ?
C35 C31 C9 119.7(4) . . ?
C43 C31 C9 123.0(4) . . ?
C43 C31 C35 117.4(3) . . ?
C2 C33 C29 121.6(4) . . ?
C2 C33 H33 119.2 . . ?
C29 C33 H33 119.2 . . ?
C31 C35 H35 119.1 . . ?
C31 C35 C39 121.7(4) . . ?
C39 C35 H35 119.1 . . ?
C2 C37 H37A 109.5 . . ?
C2 C37 H37B 109.5 . . ?
C2 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C3 C39 C35 120.0(3) . . ?
C3 C39 H39 120.0 . . ?
C35 C39 H39 120.0 . . ?
C21 C41 C27 118.7(4) . . ?
C21 C41 H41 120.6 . . ?
C27 C41 H41 120.6 . . ?
C5 C43 H43 118.8 . . ?
C31 C43 C5 122.4(4) . . ?
C31 C43 H43 118.8 . . ?
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
S1 O6 1.477(2) . ?
S1 C4 1.821(3) . ?
S1 C6 1.792(3) . ?
S4 O1 1.441(3) . ?
S4 O4 1.424(2) . ?
S4 C8 1.751(3) . ?
S4 C10 1.752(3) . ?
F1 C20 1.361(4) . ?
C1 C4 1.474(4) . ?
C1 C12 1.365(4) . ?
C1 C14 1.391(4) . ?
C4 C10 1.318(4) . ?
C6 C18 1.366(4) . ?
C6 C38 1.362(5) . ?
C8 C24 1.354(5) . ?
C8 C28 1.356(5) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C12 C22 1.385(4) . ?
C14 H14 0.9300 . ?
C14 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C20 1.341(5) . ?
C18 H18 0.9300 . ?
C18 C44 1.382(5) . ?
C20 C22 1.361(5) . ?
C22 H22 0.9300 . ?
C24 H24 0.9300 . ?
C24 C32 1.380(5) . ?
C26 H26 0.9300 . ?
C26 C38 1.380(5) . ?
C26 C40 1.375(6) . ?
C28 H28 0.9300 . ?
C28 C30 1.371(6) . ?
C30 H30 0.9300 . ?
C30 C42 1.351(6) . ?
C32 H32 0.9300 . ?
C32 C42 1.351(6) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C34 C42 1.525(5) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36 C40 1.518(5) . ?
C38 H38 0.9300 . ?
C40 C44 1.362(6) . ?
C44 H44 0.9300 . ?
S2 O3 1.483(2) . ?
S2 C23 1.790(3) . ?
S2 C25 1.828(3) . ?
S3 O2 1.441(3) . ?
S3 O5 1.421(2) . ?
S3 C3 1.754(3) . ?
S3 C13 1.754(3) . ?
F2 C21 1.354(4) . ?
C2 C19 1.366(5) . ?
C2 C33 1.369(5) . ?
C2 C37 1.514(5) . ?
C3 C5 1.361(4) . ?
C3 C39 1.368(5) . ?
C5 H5 0.9300 . ?
C5 C43 1.379(5) . ?
C7 H7 0.9300 . ?
C7 C19 1.382(5) . ?
C7 C23 1.367(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C31 1.509(5) . ?
C11 C15 1.373(4) . ?
C11 C25 1.470(4) . ?
C11 C27 1.391(4) . ?
C13 H13 0.9300 . ?
C13 C25 1.314(4) . ?
C15 H15 0.9300 . ?
C15 C17 1.366(5) . ?
C17 H17 0.9300 . ?
C17 C21 1.362(6) . ?
C19 H19 0.9300 . ?
C21 C41 1.362(6) . ?
C23 C29 1.360(4) . ?
C27 H27 0.9300 . ?
C27 C41 1.377(4) . ?
C29 H29 0.9300 . ?
C29 C33 1.373(5) . ?
C31 C35 1.358(5) . ?
C31 C43 1.351(5) . ?
C33 H33 0.9300 . ?
C35 H35 0.9300 . ?
C35 C39 1.375(5) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C39 H39 0.9300 . ?
C41 H41 0.9300 . ?
C43 H43 0.9300 . ?
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
S1 C4 C10 S4 178.15(16) . . . . ?
S1 C6 C18 C44 178.2(3) . . . . ?
S1 C6 C38 C26 -177.8(3) . . . . ?
S4 C8 C24 C32 -177.6(3) . . . . ?
S4 C8 C28 C30 177.6(3) . . . . ?
F1 C20 C22 C12 -180.0(3) . . . . ?
O1 S4 C8 C24 21.4(4) . . . . ?
O1 S4 C8 C28 -157.5(3) . . . . ?
O1 S4 C10 C4 138.0(3) . . . . ?
O4 S4 C8 C24 152.4(3) . . . . ?
O4 S4 C8 C28 -26.5(3) . . . . ?
O4 S4 C10 C4 7.5(3) . . . . ?
O6 S1 C4 C1 -175.5(2) . . . . ?
O6 S1 C4 C10 7.2(3) . . . . ?
O6 S1 C6 C18 -160.8(3) . . . . ?
O6 S1 C6 C38 16.6(3) . . . . ?
C1 C4 C10 S4 1.5(5) . . . . ?
C1 C12 C22 C20 -0.6(5) . . . . ?
C1 C14 C16 C20 -1.1(5) . . . . ?
C4 S1 C6 C18 89.2(3) . . . . ?
C4 S1 C6 C38 -93.5(3) . . . . ?
C4 C1 C12 C22 173.5(3) . . . . ?
C4 C1 C14 C16 -172.7(3) . . . . ?
C6 S1 C4 C1 -64.4(2) . . . . ?
C6 S1 C4 C10 118.2(3) . . . . ?
C6 C18 C44 C40 -0.9(6) . . . . ?
C8 S4 C10 C4 -107.7(3) . . . . ?
C8 C24 C32 C42 0.3(7) . . . . ?
C8 C28 C30 C42 -0.4(7) . . . . ?
C10 S4 C8 C24 -90.9(3) . . . . ?
C10 S4 C8 C28 90.2(3) . . . . ?
C12 C1 C4 S1 -61.9(3) . . . . ?
C12 C1 C4 C10 114.8(4) . . . . ?
C12 C1 C14 C16 -0.4(5) . . . . ?
C14 C1 C4 S1 110.3(3) . . . . ?
C14 C1 C4 C10 -73.0(4) . . . . ?
C14 C1 C12 C22 1.3(5) . . . . ?
C14 C16 C20 F1 -179.2(3) . . . . ?
C14 C16 C20 C22 1.9(6) . . . . ?
C16 C20 C22 C12 -1.0(6) . . . . ?
C18 C6 C38 C26 -0.4(5) . . . . ?
C24 C8 C28 C30 -1.3(6) . . . . ?
C24 C32 C42 C30 -2.0(7) . . . . ?
C24 C32 C42 C34 179.0(4) . . . . ?
C26 C40 C44 C18 0.4(6) . . . . ?
C28 C8 C24 C32 1.3(6) . . . . ?
C28 C30 C42 C32 2.0(7) . . . . ?
C28 C30 C42 C34 -179.0(4) . . . . ?
C36 C40 C44 C18 -178.1(4) . . . . ?
C38 C6 C18 C44 0.8(5) . . . . ?
C38 C26 C40 C36 178.6(4) . . . . ?
C38 C26 C40 C44 0.0(7) . . . . ?
C40 C26 C38 C6 -0.1(6) . . . . ?
S2 C23 C29 C33 -178.6(3) . . . . ?
S3 C3 C5 C43 -178.4(3) . . . . ?
S3 C3 C39 C35 177.4(3) . . . . ?
S3 C13 C25 S2 175.63(17) . . . . ?
S3 C13 C25 C11 -2.6(5) . . . . ?
F2 C21 C41 C27 -179.7(3) . . . . ?
O2 S3 C3 C5 14.3(3) . . . . ?
O2 S3 C3 C39 -164.1(3) . . . . ?
O2 S3 C13 C25 137.8(3) . . . . ?
O3 S2 C23 C7 -153.6(3) . . . . ?
O3 S2 C23 C29 24.6(3) . . . . ?
O3 S2 C25 C11 -171.9(2) . . . . ?
O3 S2 C25 C13 9.5(3) . . . . ?
O5 S3 C3 C5 145.6(3) . . . . ?
O5 S3 C3 C39 -32.9(3) . . . . ?
O5 S3 C13 C25 6.9(4) . . . . ?
C3 S3 C13 C25 -108.1(3) . . . . ?
C3 C5 C43 C31 1.7(6) . . . . ?
C5 C3 C39 C35 -1.1(6) . . . . ?
C7 C23 C29 C33 -0.5(5) . . . . ?
C9 C31 C35 C39 -179.2(4) . . . . ?
C9 C31 C43 C5 178.1(4) . . . . ?
C11 C15 C17 C21 -0.5(6) . . . . ?
C11 C27 C41 C21 -1.0(5) . . . . ?
C13 S3 C3 C5 -98.1(3) . . . . ?
C13 S3 C3 C39 83.4(3) . . . . ?
C15 C11 C25 S2 -57.6(3) . . . . ?
C15 C11 C25 C13 120.7(4) . . . . ?
C15 C11 C27 C41 0.5(5) . . . . ?
C15 C17 C21 F2 -179.6(3) . . . . ?
C15 C17 C21 C41 0.0(6) . . . . ?
C17 C21 C41 C27 0.7(6) . . . . ?
C19 C2 C33 C29 0.1(6) . . . . ?
C19 C7 C23 S2 179.6(3) . . . . ?
C19 C7 C23 C29 1.4(5) . . . . ?
C23 S2 C25 C11 -60.9(2) . . . . ?
C23 S2 C25 C13 120.5(3) . . . . ?
C23 C7 C19 C2 -1.7(6) . . . . ?
C23 C29 C33 C2 -0.3(6) . . . . ?
C25 S2 C23 C7 96.6(3) . . . . ?
C25 S2 C23 C29 -85.2(3) . . . . ?
C25 C11 C15 C17 173.3(3) . . . . ?
C25 C11 C27 C41 -172.6(3) . . . . ?
C27 C11 C15 C17 0.2(5) . . . . ?
C27 C11 C25 S2 115.5(3) . . . . ?
C27 C11 C25 C13 -66.2(5) . . . . ?
C31 C35 C39 C3 0.5(6) . . . . ?
C33 C2 C19 C7 0.9(6) . . . . ?
C35 C31 C43 C5 -2.2(6) . . . . ?
C37 C2 C19 C7 -178.3(4) . . . . ?
C37 C2 C33 C29 179.3(4) . . . . ?
C39 C3 C5 C43 0.1(6) . . . . ?
C43 C31 C35 C39 1.2(6) . . . . ?
