#------------------------------------------------------------------------------
#$Date: 2022-03-22 01:14:23 +0200 (Tue, 22 Mar 2022) $
#$Revision: 273877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/66/1566673.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_1566673
loop_
_publ_author_name
'Nguyen, Vu T.'
'Haug, Graham C.'
'Nguyen, Viet D.'
'Vuong, Ngan T. H.'
'Karki, Guna B.'
'Arman, Hadi'
'Larionov, Oleg V.'
_publ_section_title
;
 Functional Group Divergence and the Structural Basis of Acridine
 Photocatalysis Revealed by Direct Decarboxysulfonylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00789D
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 F O3 S'
_chemical_formula_sum            'C10 H11 F O3 S'
_chemical_formula_weight         230.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-23
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.71650(10)
_cell_length_b                   12.1828(2)
_cell_length_c                   14.7356(2)
_cell_measurement_reflns_used    14719
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3720
_cell_measurement_theta_min      3.6020
_cell_volume                     1025.77(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00 -16.00   0.50    0.06    --  -46.87 131.00-107.00  150
  2  ω   -120.00 -70.00   0.50    0.06    --  -46.87-131.00-177.00  100
  3  ω    -95.00 -19.00   0.50    0.06    --  -46.87 137.00  69.00  152
  4  ω   -120.00 -66.00   0.50    0.06    --  -46.87-137.00   6.00  108
  5  ω     38.00  99.00   0.50    0.06    --   46.87-131.00-177.00  122
  6  ω    -90.00 -16.00   0.50    0.24    --  -88.50 131.00-107.00  148
  7  ω   -160.00 -70.00   0.50    0.24    --  -88.50-131.00-177.00  180
  8  ω    -95.00 -19.00   0.50    0.24    --  -88.50 137.00  69.00  152
  9  ω     41.00 120.00   0.50    0.24    --  106.69-137.00   6.00  158
 10  ω     87.00 178.00   0.50    0.24    --  106.69 137.00  69.00  182
 11  ω     38.00 116.00   0.50    0.24    --  106.69-131.00-177.00  156
 12  ω     91.00 178.00   0.50    0.24    --  106.69 131.00-107.00  174
 13  ω   -120.00 -87.00   0.50    0.06    --  -46.87-125.00 -60.00   66
 14  ω   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00   0.00   74
 15  ω   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00 -90.00   74
 16  ω     83.00 120.00   0.50    0.06    --   46.87  57.00 120.00   74
 17  ω     41.00 102.00   0.50    0.06    --   46.87-137.00   6.00  122
 18  ω    -51.00 -16.00   0.50    0.24    --  -88.50  45.00 120.00   70
 19  ω   -160.00 -91.00   0.50    0.24    --  -88.50 -61.00 -90.00  138
 20  ω    -51.00 -16.00   0.50    0.24    --  -88.50  45.00  30.00   70
 21  ω    -51.00 -16.00   0.50    0.24    --  -88.50  45.00  60.00   70
 22  ω     92.00 178.00   0.50    0.24    --  106.69  45.00   0.00  172
 23  ω     34.00 105.00   0.50    0.24    --  106.69 -94.00-150.00  142
 24  ω     34.00  71.00   0.50    0.24    --  106.69 -61.00-120.00   74
 25  ω     34.00  71.00   0.50    0.24    --  106.69 -61.00-180.00   74
 26  ω     34.00  71.00   0.50    0.24    --  106.69 -61.00 -60.00   74
 27  ω     95.00 178.00   0.50    0.24    --  106.69 125.00 -60.00  166
 28  ω     34.00 101.00   0.50    0.24    --  106.69 -77.00 150.00  134
 29  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 -60.00  178
 30  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 150.00  178
 31  ω   -121.00 -56.00   0.50    0.06    --  -46.87 -37.00-150.00  130
 32  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00  60.00  178
 33  ω     53.00  78.00   0.50    0.24    --  106.69-132.00-177.00   50
 34  ω   -118.00 -91.00   0.50    0.06    --  -46.87-125.00 120.00   54
 35  ω   -150.00-108.00   0.50    0.24    --  -88.50 -77.00  30.00   84
 36  ω    -41.00 -16.00   0.50    0.24    --  -88.50  45.00 -60.00   50
 37  ω   -158.00-109.00   0.50    0.24    --  -88.50 -94.00 -60.00   98
 38  ω    -51.00 -26.00   0.50    0.24    --  -88.50  45.00  90.00   50
 39  ω   -149.00-123.00   0.50    0.24    --  -88.50 -77.00-120.00   52
 40  ω     34.00  59.00   0.50    0.24    --  106.69 -61.00  90.00   50
 41  ω     47.00 100.00   0.50    0.24    --  106.69 -77.00 -30.00  106
 42  ω     36.00 111.00   0.50    0.24    --  106.69-125.00  90.00  150
 43  ω    149.00 175.00   0.50    0.24    --  106.69  45.00-120.00   52
 44  ω     76.00 101.00   0.50    0.24    --  106.69 -77.00-150.00   50
 45  ω     98.00 125.00   0.50    0.24    --  106.69  45.00-120.00   54
 46  ω     34.00  59.00   0.50    0.24    --  106.69 -61.00-150.00   50
 47  ω     34.00  60.00   0.50    0.24    --  106.69 -61.00  60.00   52
 48  ω     34.00  68.00   0.50    0.24    --  106.69 -61.00   0.00   68
 49  ω   -119.00 -94.00   0.50    0.06    --  -46.87-132.00-177.00   50
 50  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 120.00  178
 51  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 -90.00  178
 52  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00   0.00  178
 53  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00-120.00  178
 54  ω   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00 120.00   74
 55  ω     32.00 121.00   0.50    0.06    --   46.87  37.00  90.00  178
 56  ω     32.00 121.00   0.50    0.06    --   46.87  37.00 -60.00  178
 57  ω     32.00 121.00   0.50    0.06    --   46.87  37.00 -90.00  178
 58  ω     32.00 121.00   0.50    0.06    --   46.87  37.00-180.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0212245000
_diffrn_orient_matrix_UB_12      0.1000643000
_diffrn_orient_matrix_UB_13      -0.0631181000
_diffrn_orient_matrix_UB_21      -0.0356939000
_diffrn_orient_matrix_UB_22      0.0772927000
_diffrn_orient_matrix_UB_23      0.0811861000
_diffrn_orient_matrix_UB_31      0.2663755000
_diffrn_orient_matrix_UB_32      0.0023743000
_diffrn_orient_matrix_UB_33      0.0191126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22324
_diffrn_reflns_point_group_measured_fraction_full 0.798
_diffrn_reflns_point_group_measured_fraction_max 0.752
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.622
_diffrn_reflns_theta_min         3.628
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0303
_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)+(0.0528P)²+0.3443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_full    0.595
_reflns_Friedel_fraction_max     0.530
_reflns_number_gt                3185
_reflns_number_total             3241
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd130b
_cod_database_code               1566673
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O S F'
_chemical_oxdiff_usercomment     'K44-9 FLou'
_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.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C2(H2A,H2B), C13(H13A,H13B), C1(H1A,H1B),
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C6(H6), C7(H7), C10(H10), C17(H17), C18(H18), C8(H8), C16(H16),
 C9(H9), C19(H19)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.807
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
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
S2 S 0.96734(11) 1.02137(5) 0.63392(5) 0.01881(17) Uani 1 1 d . . . . .
S1 S 0.47774(11) 1.09073(5) 0.36309(5) 0.01884(17) Uani 1 1 d . . . . .
F1 F 0.4407(3) 1.10184(15) 0.46708(13) 0.0286(4) Uani 1 1 d . . . . .
F2 F 0.9121(3) 1.03752(15) 0.53006(13) 0.0279(4) Uani 1 1 d . . . . .
O3 O -0.1481(4) 0.76735(17) 0.41750(15) 0.0237(5) Uani 1 1 d . . . . .
O6 O 0.3126(4) 0.69845(17) 0.56882(15) 0.0243(5) Uani 1 1 d . . . . .
O4 O 1.2050(4) 1.05120(19) 0.64711(16) 0.0265(5) Uani 1 1 d . . . . .
O2 O 0.2846(4) 1.14410(18) 0.32055(17) 0.0294(5) Uani 1 1 d . . . . .
O1 O 0.7069(4) 1.12901(18) 0.34844(16) 0.0270(5) Uani 1 1 d . . . . .
O5 O 0.7913(4) 1.07977(18) 0.67924(17) 0.0285(5) Uani 1 1 d . . . . .
C14 C 0.4801(5) 0.6499(2) 0.60394(19) 0.0177(6) Uani 1 1 d . . . . .
C11 C 0.9336(5) 0.8791(2) 0.6434(2) 0.0190(6) Uani 1 1 d . . . . .
H11A H 1.046842 0.843959 0.605230 0.023 Uiso 1 1 calc R U . . .
H11B H 0.971271 0.858194 0.705648 0.023 Uiso 1 1 calc R U . . .
C5 C -0.0003(6) 0.5952(2) 0.3739(2) 0.0161(6) Uani 1 1 d . . . . .
C20 C 0.6619(5) 0.4706(2) 0.6575(2) 0.0193(6) Uani 1 1 d . . . . .
H20 H 0.787989 0.509047 0.683128 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6914(5) 0.8342(2) 0.6177(2) 0.0192(6) Uani 1 1 d . . . . .
H12A H 0.573487 0.869438 0.653670 0.023 Uiso 1 1 calc R U . . .
H12B H 0.654665 0.848008 0.554058 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2345(6) 0.8970(2) 0.3809(2) 0.0206(6) Uani 1 1 d . . . . .
H2A H 0.221805 0.904562 0.446139 0.025 Uiso 1 1 calc R U . . .
H2B H 0.102832 0.934641 0.351832 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4771(6) 0.5276(2) 0.61427(19) 0.0184(6) Uani 1 1 d . . . . .
C6 C -0.1902(5) 0.5398(2) 0.4083(2) 0.0195(6) Uani 1 1 d . . . . .
H6 H -0.310147 0.579392 0.434274 0.023 Uiso 1 1 calc R U . . .
C13 C 0.6955(5) 0.7114(2) 0.6362(2) 0.0199(6) Uani 1 1 d . . . . .
H13A H 0.830146 0.680044 0.607137 0.024 Uiso 1 1 calc R U . . .
H13B H 0.716809 0.700067 0.701038 0.024 Uiso 1 1 calc R U . . .
C7 C -0.2035(6) 0.4264(3) 0.4047(2) 0.0224(6) Uani 1 1 d . . . . .
H7 H -0.330769 0.390212 0.428778 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0136(5) 0.7177(2) 0.38452(19) 0.0185(6) Uani 1 1 d . . . . .
C10 C 0.1763(5) 0.5352(2) 0.3324(2) 0.0193(6) Uani 1 1 d . . . . .
H10 H 0.302777 0.571305 0.307601 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2825(6) 0.3548(3) 0.5836(2) 0.0222(6) Uani 1 1 d . . . . .
H17 H 0.155588 0.315849 0.559245 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4673(6) 0.2995(2) 0.6251(2) 0.0222(6) Uani 1 1 d . . . . .
H18 H 0.464779 0.223280 0.628276 0.027 Uiso 1 1 calc R U . . .
C8 C -0.0262(6) 0.3667(2) 0.3649(2) 0.0216(6) Uani 1 1 d . . . . .
H8 H -0.033545 0.290473 0.362766 0.026 Uiso 1 1 calc R U . . .
C1 C 0.4626(5) 0.9480(2) 0.3510(2) 0.0187(6) Uani 1 1 d . . . . .
H1A H 0.483980 0.929734 0.287700 0.022 Uiso 1 1 calc R U . . .
H1B H 0.590941 0.915347 0.386008 0.022 Uiso 1 1 calc R U . . .
C16 C 0.2859(5) 0.4688(3) 0.5783(2) 0.0203(6) Uani 1 1 d . . . . .
H16 H 0.160631 0.505924 0.550806 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1615(6) 0.4215(3) 0.3284(2) 0.0219(6) Uani 1 1 d . . . . .
H9 H 0.278827 0.381678 0.300958 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6570(5) 0.3571(3) 0.6621(2) 0.0215(6) Uani 1 1 d . . . . .
H19 H 0.780902 0.319295 0.689934 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2298(5) 0.7765(2) 0.3551(2) 0.0195(6) Uani 1 1 d . . . . .
H3A H 0.240104 0.770276 0.289724 0.023 Uiso 1 1 calc R U . . .
H3B H 0.366234 0.740681 0.382376 0.023 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 0.0181 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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 1 0 0.0649
0 6 6 0.0302
0 -2 -9 0.0272
4 0 -1 0.0776
0 -6 -6 0.0207
0 2 9 0.0154
0 8 -2 0.0300
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
F2 S2 C11 100.55(13) . . ?
O4 S2 F2 105.47(12) . . ?
O4 S2 O5 119.97(15) . . ?
O4 S2 C11 110.56(15) . . ?
O5 S2 F2 105.82(14) . . ?
O5 S2 C11 112.23(14) . . ?
F1 S1 C1 100.30(13) . . ?
O2 S1 F1 105.60(13) . . ?
O2 S1 O1 119.76(15) . . ?
O2 S1 C1 112.12(15) . . ?
O1 S1 F1 105.98(12) . . ?
O1 S1 C1 110.84(14) . . ?
O6 C14 C15 120.7(3) . . ?
O6 C14 C13 120.9(3) . . ?
C15 C14 C13 118.3(2) . . ?
S2 C11 H11A 108.3 . . ?
S2 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 S2 115.9(2) . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 C10 119.2(3) . . ?
C10 C5 C4 121.8(3) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C15 120.1(3) . . ?
C11 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 C11 107.4(2) . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H2A C2 H2B 108.3 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C3 C2 C1 109.3(2) . . ?
C20 C15 C14 121.9(3) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 C20 119.2(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C14 C13 C12 115.2(2) . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
O3 C4 C5 119.8(3) . . ?
O3 C4 C3 121.2(3) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
S1 C1 H1A 108.6 . . ?
S1 C1 H1B 108.6 . . ?
C2 C1 S1 114.6(2) . . ?
C2 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 C2 113.4(2) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
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
S2 F2 1.5657(19) . ?
S2 O4 1.414(2) . ?
S2 O5 1.416(2) . ?
S2 C11 1.750(3) . ?
S1 F1 1.5591(19) . ?
S1 O2 1.412(2) . ?
S1 O1 1.413(2) . ?
S1 C1 1.750(3) . ?
O3 C4 1.218(4) . ?
O6 C14 1.227(4) . ?
C14 C15 1.497(4) . ?
C14 C13 1.506(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.526(4) . ?
C5 C6 1.387(4) . ?
C5 C4 1.501(4) . ?
C5 C10 1.402(4) . ?
C20 H20 0.9300 . ?
C20 C15 1.401(4) . ?
C20 C19 1.386(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.520(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.522(4) . ?
C2 C3 1.517(4) . ?
C15 C16 1.398(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.392(5) . ?
C4 C3 1.504(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.389(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C17 C16 1.391(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C16 H16 0.9300 . ?
C9 H9 0.9300 . ?
C19 H19 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
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
S2 C11 C12 C13 -176.6(2) . . . . ?
F1 S1 C1 C2 58.5(2) . . . . ?
F2 S2 C11 C12 -60.8(2) . . . . ?
O3 C4 C3 C2 6.8(4) . . . . ?
O6 C14 C15 C20 -177.3(3) . . . . ?
O6 C14 C15 C16 3.8(4) . . . . ?
O6 C14 C13 C12 -2.7(4) . . . . ?
O4 S2 C11 C12 -171.8(2) . . . . ?
O2 S1 C1 C2 -53.1(3) . . . . ?
O1 S1 C1 C2 170.2(2) . . . . ?
O5 S2 C11 C12 51.3(3) . . . . ?
C14 C15 C16 C17 177.4(3) . . . . ?
C11 C12 C13 C14 -172.7(2) . . . . ?
C5 C6 C7 C8 -0.9(5) . . . . ?
C5 C4 C3 C2 -172.4(3) . . . . ?
C5 C10 C9 C8 0.1(5) . . . . ?
C20 C15 C16 C17 -1.5(4) . . . . ?
C15 C14 C13 C12 176.2(2) . . . . ?
C15 C20 C19 C18 -1.0(5) . . . . ?
C6 C5 C4 O3 -4.9(4) . . . . ?
C6 C5 C4 C3 174.3(3) . . . . ?
C6 C5 C10 C9 -1.6(4) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C13 C14 C15 C20 3.8(4) . . . . ?
C13 C14 C15 C16 -175.1(3) . . . . ?
C7 C8 C9 C10 1.0(5) . . . . ?
C4 C5 C6 C7 -176.3(3) . . . . ?
C4 C5 C10 C9 176.6(3) . . . . ?
C10 C5 C6 C7 2.0(4) . . . . ?
C10 C5 C4 O3 176.9(3) . . . . ?
C10 C5 C4 C3 -3.9(4) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C17 C16 C15 0.5(4) . . . . ?
C1 C2 C3 C4 178.2(2) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C19 C20 C15 C14 -177.1(3) . . . . ?
C19 C20 C15 C16 1.8(4) . . . . ?
C3 C2 C1 S1 172.3(2) . . . . ?
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
-3.6660 1.1598 -0.2010 0.0509 0.2042 -0.9776
0.0107 6.1239 6.0450 0.2315 0.9637 0.1329
-0.3225 -2.0390 -9.1738 0.3682 -0.8909 -0.2661
3.6985 -0.3744 -0.9287 0.0997 -0.2364 0.9665
0.1132 -6.1433 -6.0187 -0.2324 -0.9675 -0.0995
0.1992 2.0511 9.2027 -0.3714 0.8986 0.2338
0.3716 7.6216 -2.3934 0.9216 0.3815 0.0713
