# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_final
_database_code_depnum_ccdc_archive 'CCDC 2427870'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 F O3 S'
_chemical_formula_sum            'C15 H13 F O3 S'
_chemical_formula_weight         292.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H13FO3S
_chemical_oxdiff_usercomment     colorless
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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   9.8930(2)
_cell_length_b                   14.4664(3)
_cell_length_c                   9.7170(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.429(2)
_cell_angle_gamma                90
_cell_volume                     1346.79(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3687
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2070
_cell_measurement_theta_min      5.5300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5113
_diffrn_reflns_point_group_measured_fraction_full 0.649
_diffrn_reflns_point_group_measured_fraction_max 0.625
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.697
_diffrn_reflns_theta_min         5.538
_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 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00 -32.00   0.50    3.00    --  -49.53  94.00  95.00   90
  2  ω    -23.00  17.00   0.50    3.00    --  -49.53  94.00  95.00   80
  3  ω      5.00  49.00   0.50    3.00    --   49.53 -94.00 -15.00   88
  4  ω    -72.00 -46.00   0.50   10.00    --  -90.00  94.00  95.00   52
  5  ω     51.00  77.00   0.50   10.00    --  111.50 -94.00 -15.00   52
  6  ω    105.00 165.00   0.50   10.00    --  111.50  94.00  95.00  120
  7  ω   -118.00 -93.00   0.50    3.00    --  -49.53-125.00 120.00   50
  8  ω   -118.00 -93.00   0.50    3.00    --  -49.53-125.00  60.00   50
  9  ω   -115.00 -88.00   0.50    3.00    --  -49.53-125.00 150.00   54
 10  ω   -118.00 -93.00   0.50    3.00    --  -49.53-125.00  90.00   50
 11  ω     87.00 118.00   0.50    3.00    --   49.53  57.00 -90.00   62
 12  ω     84.00 116.00   0.50    3.00    --   49.53  57.00-120.00   64
 13  ω    -50.00 -23.00   0.50   10.00    --  -90.00  45.00  30.00   54
 14  ω    -48.00 -23.00   0.50   10.00    --  -90.00  45.00 -60.00   50
 15  ω   -151.00-112.00   0.50   10.00    --  -90.00 -94.00 -15.00   78
 16  ω     43.00  72.00   0.50   10.00    --  111.50 -61.00   0.00   58
 17  ω    108.00 164.00   0.50   10.00    --  111.50  15.00-180.00  112
 18  ω     78.00 104.00   0.50   10.00    --  111.50-125.00  90.00   52
 19  ω     46.00  72.00   0.50   10.00    --  111.50 -61.00 120.00   52
 20  ω     42.00  71.00   0.50   10.00    --  111.50 -61.00 150.00   58
 21  ω     46.00  75.00   0.50   10.00    --  111.50-125.00  90.00   58
 22  ω     42.00  70.00   0.50   10.00    --  111.50 -61.00 -90.00   56
 23  ω     41.00  66.00   0.50   10.00    --  111.50 -61.00-180.00   50
 24  ω    149.00 177.00   0.50   10.00    --  111.50  30.00  30.00   56
 25  ω     42.00  71.00   0.50   10.00    --  111.50 -61.00-120.00   58
 26  ω     49.00  86.00   0.50   10.00    --  111.50 -95.00  90.00   74
 27  ω     41.00 101.00   0.50   10.00    --  111.50 -77.00 120.00  120
 28  ω    106.00 132.00   0.50   10.00    --  111.50  30.00  30.00   52
 29  ω     46.00  71.00   0.50   10.00    --  111.50 -61.00  30.00   50
 30  ω     43.00  69.00   0.50   10.00    --  111.50 -95.00-120.00   52
 31  ω     73.00 100.00   0.50   10.00    --  111.50 -95.00-120.00   54
 32  ω     46.00 104.00   0.50   10.00    --  111.50 -95.00   0.00  116
 33  ω     42.00  67.00   0.50   10.00    --  111.50 -61.00-150.00   50
;
_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      0.0749292000
_diffrn_orient_matrix_UB_12      -0.0761907000
_diffrn_orient_matrix_UB_13      -0.0636420000
_diffrn_orient_matrix_UB_21      -0.1282298000
_diffrn_orient_matrix_UB_22      -0.0632826000
_diffrn_orient_matrix_UB_23      -0.0161652000
_diffrn_orient_matrix_UB_31      -0.0617486000
_diffrn_orient_matrix_UB_32      0.0391466000
_diffrn_orient_matrix_UB_33      -0.1498979000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.274
_reflns_Friedel_fraction_full    0.297
_reflns_Friedel_fraction_max     0.270
_reflns_number_gt                1784
_reflns_number_total             1831
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1831
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.078
_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)+(0.0616P)²+0.4461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0891
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
O2 O 0.4272(3) 0.44375(15) 0.7090(2) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.6408(3) 0.5683(2) 0.6462(3) 0.0182(5) Uani 1 1 d . . . . .
O3 O 0.7279(3) 0.53927(14) 0.7474(3) 0.0261(5) Uani 1 1 d . . . . .
C3 C 0.5976(3) 0.6663(2) 0.6289(3) 0.0179(5) Uani 1 1 d . . . . .
C4 C 0.6422(3) 0.7246(2) 0.7467(3) 0.0222(6) Uani 1 1 d . . . . .
H4 H 0.692003 0.699645 0.835280 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6138(3) 0.8184(2) 0.7344(4) 0.0249(6) Uani 1 1 d . . . . .
H5 H 0.645395 0.857589 0.814354 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5388(3) 0.8560(2) 0.6049(4) 0.0242(6) Uani 1 1 d . . . . .
C7 C 0.4940(3) 0.7975(2) 0.4894(3) 0.0233(6) Uani 1 1 d . . . . .
H7 H 0.443365 0.822598 0.401254 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5213(3) 0.70346(19) 0.4993(3) 0.0213(6) Uani 1 1 d . . . . .
H8 H 0.488643 0.664501 0.419213 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5051(4) 0.9579(2) 0.5914(5) 0.0315(8) Uani 1 1 d . . . . .
H9A H 0.419618 0.967420 0.516205 0.047 Uiso 1 1 calc R U . . .
H9B H 0.582396 0.991284 0.567599 0.047 Uiso 1 1 calc R U . . .
H9C H 0.491364 0.981038 0.681745 0.047 Uiso 1 1 calc R U . . .
C10 C 0.3641(3) 0.35914(19) 0.4660(3) 0.0194(6) Uani 1 1 d . . . . .
C11 C 0.4012(4) 0.27653(18) 0.5401(4) 0.0222(6) Uani 1 1 d . . . . .
H11 H 0.446510 0.276732 0.638549 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3699(4) 0.1941(2) 0.4659(4) 0.0285(7) Uani 1 1 d . . . . .
H12 H 0.393639 0.136945 0.513959 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3044(4) 0.1947(2) 0.3223(4) 0.0299(7) Uani 1 1 d . . . . .
H13 H 0.282783 0.137888 0.272656 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2701(4) 0.2778(2) 0.2503(4) 0.0286(7) Uani 1 1 d . . . . .
H14 H 0.226622 0.277460 0.151433 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2988(3) 0.3612(2) 0.3220(3) 0.0230(6) Uani 1 1 d . . . . .
H15 H 0.274477 0.418225 0.273793 0.028 Uiso 1 1 calc R U . . .
S1 S 0.40323(6) 0.46356(4) 0.55975(6) 0.01657(18) Uani 1 1 d . . . . .
F1 F 0.65285(19) 0.41957(11) 0.54595(19) 0.0220(4) Uani 1 1 d . . . . .
O1 O 0.3043(2) 0.53377(14) 0.4972(3) 0.0234(5) Uani 1 1 d . . . . .
C1 C 0.5719(3) 0.49808(19) 0.5301(3) 0.0193(6) Uani 1 1 d . . . . .
H1 H 0.560067 0.525163 0.433165 0.023 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
O2 S1 1.439(2) . ?
C2 O3 1.210(4) . ?
C2 C3 1.478(4) . ?
C2 C1 1.545(4) . ?
C3 C4 1.401(4) . ?
C3 C8 1.404(4) . ?
C4 C5 1.385(4) . ?
C5 C6 1.401(5) . ?
C6 C7 1.387(5) . ?
C6 C9 1.510(4) . ?
C7 C8 1.386(4) . ?
C10 C11 1.396(4) . ?
C10 C15 1.387(4) . ?
C10 S1 1.757(3) . ?
C11 C12 1.388(4) . ?
C12 C13 1.384(5) . ?
C13 C14 1.390(5) . ?
C14 C15 1.387(4) . ?
S1 O1 1.436(2) . ?
S1 C1 1.832(3) . ?
F1 C1 1.376(3) . ?

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
O3 C2 C3 123.6(3) . . ?
O3 C2 C1 117.4(3) . . ?
C3 C2 C1 119.0(3) . . ?
C4 C3 C2 117.4(3) . . ?
C4 C3 C8 119.5(3) . . ?
C8 C3 C2 123.0(3) . . ?
C5 C4 C3 120.2(3) . . ?
C4 C5 C6 120.6(3) . . ?
C5 C6 C9 120.9(3) . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 C9 120.4(3) . . ?
C8 C7 C6 121.7(3) . . ?
C7 C8 C3 119.3(3) . . ?
C11 C10 S1 118.2(2) . . ?
C15 C10 C11 122.3(3) . . ?
C15 C10 S1 119.5(2) . . ?
C12 C11 C10 118.1(3) . . ?
C13 C12 C11 120.4(3) . . ?
C12 C13 C14 120.5(3) . . ?
C15 C14 C13 120.4(3) . . ?
C14 C15 C10 118.3(3) . . ?
O2 S1 C10 108.12(13) . . ?
O2 S1 C1 106.55(14) . . ?
C10 S1 C1 104.14(14) . . ?
O1 S1 O2 119.41(14) . . ?
O1 S1 C10 110.49(14) . . ?
O1 S1 C1 107.01(13) . . ?
C2 C1 S1 108.6(2) . . ?
F1 C1 C2 108.8(2) . . ?
F1 C1 S1 106.55(19) . . ?

_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 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.254
####################################################################### 
# 
# 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_final_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2427872'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 F O6 S2'
_chemical_formula_sum            'C16 H15 F O6 S2'
_chemical_formula_weight         386.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H20S2O6
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.37560(10)
_cell_length_b                   10.77320(10)
_cell_length_c                   15.8510(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.9340(10)
_cell_angle_gamma                90
_cell_volume                     1750.30(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14301
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4930
_cell_measurement_theta_min      4.2820
_shelx_estimated_absorpt_T_max   0.745
_shelx_estimated_absorpt_T_min   0.309
_exptl_absorpt_coefficient_mu    3.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.2181
0 1 1 0.1421
-1 -2 2 0.2999
1 2 -2 0.1088
1 -2 2 0.2514
0 0 1 0.0784
0 0 -1 0.0428
-1 0 0 0.0945
1 0 0 0.0102

_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.105
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
0.0001 -1.0000 -1.0002 0.0006 0.0107 0.1733
-0.0001 1.0000 1.0002 -0.0006 -0.0107 -0.1733
-1.0006 -2.0000 1.9999 -0.2509 0.2358 0.1240
1.0006 2.0000 -1.9999 0.2509 -0.2358 -0.1240
0.9996 -2.0002 2.0014 0.0103 0.3802 0.0878
-0.0002 -0.0000 1.0003 -0.0304 0.0716 -0.0602
0.0002 0.0000 -1.0003 0.0304 -0.0716 0.0602
-1.0001 0.0001 -0.0007 -0.1306 -0.0722 0.0181
1.0001 -0.0001 0.0007 0.1306 0.0722 -0.0181

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18910
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.846
_diffrn_reflns_theta_min         4.314
_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 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -18.00   0.50    0.20    --  -90.00  50.00   3.00   76
  2  ω    -50.00 -18.00   0.50    0.20    --  -90.00  45.00 150.00   64
  3  ω    -50.00 -18.00   0.50    0.20    --  -90.00  45.00 120.00   64
  4  ω    -56.00  22.00   0.50    0.10    --  -49.66  50.00   3.00  156
  5  ω    -50.00 -18.00   0.50    0.20    --  -90.00  45.00-180.00   64
  6  ω   -120.00 -39.00   0.50    0.10    --  -49.66 -50.00-143.00  162
  7  ω   -118.00 -87.00   0.50    0.10    --  -49.66-125.00   0.00   62
  8  ω   -161.00 -79.00   0.50    0.20    --  -90.00 -50.00-143.00  164
  9  ω   -120.00 -82.00   0.50    0.10    --  -49.66 -57.00 -60.00   76
 10  ω   -120.00 -82.00   0.50    0.10    --  -49.66 -57.00  60.00   76
 11  ω    -21.00  58.00   0.50    0.10    --   49.66 -50.00-143.00  158
 12  ω     42.00  68.00   0.50    0.20    --  111.50 -61.00 -90.00   52
 13  ω     42.00  71.00   0.50    0.20    --  111.50 -61.00 -30.00   58
 14  ω     43.00  72.00   0.50    0.20    --  111.50 -61.00-120.00   58
 15  ω     43.00  95.00   0.50    0.20    --  111.50 -77.00 -30.00  104
 16  ω     41.00 106.00   0.50    0.20    --  111.50 -77.00  60.00  130
 17  ω     41.00  66.00   0.50    0.20    --  111.50 -61.00  90.00   50
 18  ω     41.00  72.00   0.50    0.20    --  111.50 -61.00  60.00   62
 19  ω     44.00  71.00   0.50    0.20    --  111.50 -61.00 -60.00   54
 20  ω     75.00 101.00   0.50    0.20    --  111.50 -95.00 -60.00   52
 21  ω     41.00 104.00   0.50    0.20    --  111.50 -95.00-120.00  126
 22  ω     46.00  95.00   0.50    0.20    --  111.50 -95.00-180.00   98
 23  ω     49.00  99.00   0.50    0.20    --  111.50 -95.00-150.00  100
 24  ω     59.00 103.00   0.50    0.20    --  111.50 -95.00  30.00   88
 25  ω     78.00 104.00   0.50    0.20    --  111.50 -95.00  60.00   52
 26  ω     44.00  69.00   0.50    0.20    --  111.50 -95.00  60.00   50
 27  ω    105.00 131.00   0.50    0.20    --  111.50  30.00 -90.00   52
 28  ω    103.00 139.00   0.50    0.20    --  111.50  77.00 -90.00   72
 29  ω    101.00 178.00   0.50    0.20    --  111.50  50.00   3.00  154
 30  ω    101.00 178.00   0.50    0.20    --  111.50  50.00   3.00  154
 31  ω    102.00 142.00   0.50    0.20    --  111.50  45.00  30.00   80
 32  ω    111.00 153.00   0.50    0.20    --  111.50  30.00 120.00   84
 33  ω     39.00 121.00   0.50    0.10    --   49.66  50.00   3.00  164
;
_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      0.1306017000
_diffrn_orient_matrix_UB_12      0.0297776000
_diffrn_orient_matrix_UB_13      -0.0303447000
_diffrn_orient_matrix_UB_21      0.0721303000
_diffrn_orient_matrix_UB_22      -0.0823482000
_diffrn_orient_matrix_UB_23      0.0716330000
_diffrn_orient_matrix_UB_31      -0.0180603000
_diffrn_orient_matrix_UB_32      -0.1131231000
_diffrn_orient_matrix_UB_33      -0.0601749000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3550
_reflns_number_total             3742
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00093(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.046
_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+0.8275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C12(H12), C16(H16), C14(H14), C8(H8), C13(H13),
 C9(H9), C15(H15)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S2 S 0.16348(3) 0.67183(3) 0.62290(2) 0.01738(10) Uani 1 1 d . . . . .
S1 S 0.24198(3) 0.40430(3) 0.68967(2) 0.01859(10) Uani 1 1 d . . . . .
F1 F 0.39154(7) 0.59814(7) 0.69302(5) 0.01976(17) Uani 1 1 d . . . . .
O2 O 0.13000(9) 0.58722(9) 0.80878(6) 0.0205(2) Uani 1 1 d . . . . .
O6 O 0.02943(9) 0.65039(10) 0.62964(6) 0.0245(2) Uani 1 1 d . . . . .
O1 O 0.34138(10) 0.64375(10) 0.84589(6) 0.0259(2) Uani 1 1 d . . . . .
O4 O 0.10511(10) 0.37865(10) 0.67593(7) 0.0261(2) Uani 1 1 d . . . . .
O5 O 0.21075(10) 0.65004(9) 0.54386(6) 0.0249(2) Uani 1 1 d . . . . .
O3 O 0.32470(11) 0.35634(9) 0.76362(6) 0.0265(2) Uani 1 1 d . . . . .
C11 C 0.21023(12) 0.82036(12) 0.66140(9) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.26522(12) 0.57453(12) 0.70336(8) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.22329(13) 0.35249(13) 0.52134(9) 0.0206(3) Uani 1 1 d . . . . .
H6 H 0.131716 0.360814 0.519332 0.025 Uiso 1 1 calc R U . . .
C2 C 0.25098(13) 0.60719(12) 0.79596(8) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.27565(14) 0.32346(13) 0.44854(9) 0.0235(3) Uani 1 1 d . . . . .
H7 H 0.219584 0.309191 0.396112 0.028 Uiso 1 1 calc R U . . .
C5 C 0.30842(13) 0.36915(12) 0.59755(8) 0.0182(3) Uani 1 1 d . . . . .
C10 C 0.44327(14) 0.35869(13) 0.60267(9) 0.0224(3) Uani 1 1 d . . . . .
H10 H 0.499213 0.369074 0.655615 0.027 Uiso 1 1 calc R U . . .
C12 C 0.31947(13) 0.87616(13) 0.63640(9) 0.0219(3) Uani 1 1 d . . . . .
H12 H 0.366528 0.836260 0.597246 0.026 Uiso 1 1 calc R U . . .
C16 C 0.13851(13) 0.87633(14) 0.71818(9) 0.0235(3) Uani 1 1 d . . . . .
H16 H 0.064214 0.836436 0.734056 0.028 Uiso 1 1 calc R U . . .
C14 C 0.28712(16) 1.04816(14) 0.72752(11) 0.0310(3) Uani 1 1 d . . . . .
H14 H 0.314170 1.126845 0.750916 0.037 Uiso 1 1 calc R U . . .
C8 C 0.41014(14) 0.31516(14) 0.45208(9) 0.0253(3) Uani 1 1 d . . . . .
H8 H 0.445298 0.297234 0.401553 0.030 Uiso 1 1 calc R U . . .
C3 C 0.10557(15) 0.60545(14) 0.89681(9) 0.0262(3) Uani 1 1 d . . . . .
H3A H 0.011819 0.622560 0.896810 0.031 Uiso 1 1 calc R U . . .
H3B H 0.156312 0.677444 0.922702 0.031 Uiso 1 1 calc R U . . .
C13 C 0.35762(14) 0.99165(14) 0.67030(10) 0.0275(3) Uani 1 1 d . . . . .
H13 H 0.431690 1.031973 0.654445 0.033 Uiso 1 1 calc R U . . .
C9 C 0.49384(14) 0.33276(14) 0.52860(10) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.585535 0.327023 0.530127 0.032 Uiso 1 1 calc R U . . .
C4 C 0.14523(16) 0.49001(16) 0.94819(10) 0.0316(3) Uani 1 1 d . . . . .
H4A H 0.095117 0.418984 0.922077 0.047 Uiso 1 1 calc R U . . .
H4B H 0.127777 0.501353 1.006718 0.047 Uiso 1 1 calc R U . . .
H4C H 0.238552 0.474704 0.949173 0.047 Uiso 1 1 calc R U . . .
C15 C 0.17816(16) 0.99161(14) 0.75095(10) 0.0309(3) Uani 1 1 d . . . . .
H15 H 0.130542 1.032023 0.789577 0.037 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
S2 O6 1.4302(10) . ?
S2 O5 1.4340(10) . ?
S2 C11 1.7539(13) . ?
S2 C1 1.8498(13) . ?
S1 O4 1.4299(10) . ?
S1 O3 1.4371(11) . ?
S1 C1 1.8580(13) . ?
S1 C5 1.7503(13) . ?
F1 C1 1.3696(14) . ?
O2 C2 1.3200(16) . ?
O2 C3 1.4697(16) . ?
O1 C2 1.1961(17) . ?
C11 C12 1.3937(18) . ?
C11 C16 1.3913(19) . ?
C1 C2 1.5387(17) . ?
C6 C7 1.3853(19) . ?
C6 C5 1.3929(19) . ?
C7 C8 1.391(2) . ?
C5 C10 1.3935(18) . ?
C10 C9 1.387(2) . ?
C12 C13 1.388(2) . ?
C16 C15 1.384(2) . ?
C14 C13 1.391(2) . ?
C14 C15 1.385(2) . ?
C8 C9 1.391(2) . ?
C3 C4 1.508(2) . ?

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 S2 O5 120.49(6) . . ?
O6 S2 C11 109.94(6) . . ?
O6 S2 C1 108.33(6) . . ?
O5 S2 C11 109.86(6) . . ?
O5 S2 C1 105.88(6) . . ?
C11 S2 C1 100.35(6) . . ?
O4 S1 O3 120.53(6) . . ?
O4 S1 C1 108.44(6) . . ?
O4 S1 C5 109.97(6) . . ?
O3 S1 C1 102.08(6) . . ?
O3 S1 C5 109.88(6) . . ?
C5 S1 C1 104.49(6) . . ?
C2 O2 C3 115.64(10) . . ?
C12 C11 S2 119.19(10) . . ?
C16 C11 S2 118.28(10) . . ?
C16 C11 C12 122.50(13) . . ?
S2 C1 S1 115.40(7) . . ?
F1 C1 S2 105.45(8) . . ?
F1 C1 S1 106.18(8) . . ?
F1 C1 C2 107.88(10) . . ?
C2 C1 S2 113.52(9) . . ?
C2 C1 S1 107.89(9) . . ?
C7 C6 C5 118.27(12) . . ?
O2 C2 C1 110.12(11) . . ?
O1 C2 O2 128.22(12) . . ?
O1 C2 C1 121.66(12) . . ?
C6 C7 C8 120.12(13) . . ?
C6 C5 S1 118.20(10) . . ?
C6 C5 C10 122.40(12) . . ?
C10 C5 S1 119.40(10) . . ?
C9 C10 C5 118.39(13) . . ?
C13 C12 C11 118.17(13) . . ?
C15 C16 C11 118.30(13) . . ?
C15 C14 C13 121.08(14) . . ?
C7 C8 C9 120.87(13) . . ?
O2 C3 C4 109.25(12) . . ?
C12 C13 C14 119.83(14) . . ?
C10 C9 C8 119.92(13) . . ?
C16 C15 C14 120.11(14) . . ?

_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 2.315
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# 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_final_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2427873'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Br F O5 S2'
_chemical_formula_sum            'C20 H14 Br F O5 S2'
_chemical_formula_weight         497.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H22S2O5FBr
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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.7777(2)
_cell_length_b                   14.0839(2)
_cell_length_c                   21.4027(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3851.63(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10883
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3560
_cell_measurement_theta_min      4.1020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.064
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16871
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.806
_diffrn_reflns_theta_min         4.131
_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 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00 109.00   0.50    0.75    --  111.50-125.00-150.00  120
  2  ω     49.00 103.00   0.50    0.75    --  111.50 -95.00  90.00  108
  3  ω    -24.00  23.00   0.50    0.25    --  -49.53  19.00-150.00   94
  4  ω    -25.00  21.00   0.50    0.25    --  -49.53  19.00-180.00   92
  5  ω    -26.00  23.00   0.50    0.25    --  -49.53  20.00  77.00   98
  6  ω    -68.00 -42.00   0.50    0.75    --  -90.00 124.00 141.00   52
  7  ω    -22.00   7.00   0.50    0.25    --  -49.53  19.00 150.00   58
  8  ω   -118.00 -88.00   0.50    0.25    --  -49.53-125.00  30.00   60
  9  ω    -22.00   3.00   0.50    0.25    --   49.53 -20.00 -89.00   50
 10  ω     43.00  70.00   0.50    0.75    --  111.50 -61.00-120.00   54
 11  ω     44.00  71.00   0.50    0.75    --  111.50 -61.00 -60.00   54
 12  ω     42.00  71.00   0.50    0.75    --  111.50 -61.00 -30.00   58
 13  ω    110.00 178.00   0.50    0.75    --  111.50  20.00  77.00  136
 14  ω    107.00 176.00   0.50    0.75    --  111.50  30.00 150.00  138
 15  ω    107.00 133.00   0.50    0.75    --  111.50 124.00 141.00   52
 16  ω    139.00 170.00   0.50    0.75    --  111.50 124.00 141.00   62
 17  ω    131.00 167.00   0.50    0.75    --  111.50 125.00 -60.00   72
 18  ω    130.00 156.00   0.50    0.75    --  111.50 106.00-117.00   52
;
_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      0.0248309000
_diffrn_orient_matrix_UB_12      -0.0290922000
_diffrn_orient_matrix_UB_13      -0.0677300000
_diffrn_orient_matrix_UB_21      -0.1175369000
_diffrn_orient_matrix_UB_22      0.0029720000
_diffrn_orient_matrix_UB_23      -0.0158410000
_diffrn_orient_matrix_UB_31      0.0102996000
_diffrn_orient_matrix_UB_32      0.1054458000
_diffrn_orient_matrix_UB_33      -0.0183939000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3597
_reflns_number_total             4077
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4077
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.060
_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)+(0.0379P)²+5.2652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0833
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C00P(H00P)
;
_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
S1 S 0.25403(4) 0.55962(4) 0.54571(2) 0.01682(12) Uani 1 1 d . . . . .
F1 F 0.22316(10) 0.66755(9) 0.64145(6) 0.0184(3) Uani 1 1 d . . . . .
O1 O 0.44872(13) 0.52783(12) 0.62631(8) 0.0249(3) Uani 1 1 d . . . . .
C1 C 0.27709(16) 0.58557(15) 0.63034(10) 0.0157(4) Uani 1 1 d . . . . .
S2 S 0.21824(4) 0.49214(4) 0.68216(2) 0.01792(12) Uani 1 1 d . . . . .
O2 O 0.28533(13) 0.46393(11) 0.53314(7) 0.0226(3) Uani 1 1 d . . . . .
C2 C 0.39543(17) 0.59192(16) 0.64589(10) 0.0179(4) Uani 1 1 d . . . . .
O3 O 0.14774(12) 0.58854(12) 0.53612(7) 0.0230(3) Uani 1 1 d . . . . .
C3 C 0.43588(17) 0.67188(15) 0.68451(10) 0.0168(4) Uani 1 1 d . . . . .
O4 O 0.27560(13) 0.40626(12) 0.67184(8) 0.0256(4) Uani 1 1 d . . . . .
C4 C 0.54047(17) 0.70205(16) 0.67967(10) 0.0206(4) Uani 1 1 d . . . . .
O5 O 0.21790(13) 0.53689(13) 0.74241(7) 0.0259(4) Uani 1 1 d . . . . .
C5 C 0.57957(18) 0.77078(17) 0.72007(11) 0.0239(5) Uani 1 1 d . . . . .
H5 H 0.650126 0.791180 0.716099 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5166(2) 0.80968(17) 0.76597(11) 0.0257(5) Uani 1 1 d . . . . .
H6 H 0.544315 0.855752 0.793858 0.031 Uiso 1 1 calc R U . . .
C7 C 0.37319(17) 0.71368(16) 0.73069(10) 0.0186(4) Uani 1 1 d . . . . .
H7 H 0.301924 0.695241 0.734258 0.022 Uiso 1 1 calc R U . . .
C8 C 0.33667(17) 0.63907(15) 0.50611(10) 0.0175(4) Uani 1 1 d . . . . .
C9 C 0.42262(18) 0.60301(16) 0.47362(10) 0.0210(4) Uani 1 1 d . . . . .
H9 H 0.437476 0.536916 0.474073 0.025 Uiso 1 1 calc R U . . .
C10 C 0.48590(19) 0.66526(17) 0.44071(11) 0.0234(5) Uani 1 1 d . . . . .
H10 H 0.544804 0.642075 0.418335 0.028 Uiso 1 1 calc R U . . .
C11 C 0.46302(19) 0.76161(16) 0.44050(10) 0.0223(5) Uani 1 1 d . . . . .
H11 H 0.507243 0.804188 0.418409 0.027 Uiso 1 1 calc R U . . .
C12 C 0.37609(19) 0.79670(16) 0.47225(10) 0.0220(5) Uani 1 1 d . . . . .
H12 H 0.360884 0.862707 0.471124 0.026 Uiso 1 1 calc R U . . .
C13 C 0.31158(18) 0.73563(16) 0.50553(10) 0.0201(4) Uani 1 1 d . . . . .
H13 H 0.252046 0.758830 0.527299 0.024 Uiso 1 1 calc R U . . .
C14 C 0.08902(16) 0.47935(15) 0.65632(10) 0.0167(4) Uani 1 1 d . . . . .
C15 C 0.06705(18) 0.40863(15) 0.61308(10) 0.0187(4) Uani 1 1 d . . . . .
H15 H 0.120420 0.367025 0.598751 0.022 Uiso 1 1 calc R U . . .
C16 C -0.03490(18) 0.40023(16) 0.59130(10) 0.0212(4) Uani 1 1 d . . . . .
H16 H -0.051809 0.353244 0.561101 0.025 Uiso 1 1 calc R U . . .
C17 C -0.11222(18) 0.46079(17) 0.61382(10) 0.0217(4) Uani 1 1 d . . . . .
H17 H -0.182010 0.454323 0.599117 0.026 Uiso 1 1 calc R U . . .
C18 C -0.08878(17) 0.53049(17) 0.65745(10) 0.0209(4) Uani 1 1 d . . . . .
H18 H -0.142477 0.571120 0.672544 0.025 Uiso 1 1 calc R U . . .
C19 C 0.01323(17) 0.54100(16) 0.67912(10) 0.0190(4) Uani 1 1 d . . . . .
H19 H 0.030534 0.588883 0.708629 0.023 Uiso 1 1 calc R U . . .
C00P C 0.41303(19) 0.78140(16) 0.77128(10) 0.0228(5) Uani 1 1 d . . . . .
H00P H 0.369517 0.808319 0.802614 0.027 Uiso 1 1 calc R U . . .
Br1 Br 0.63294(2) 0.65862(2) 0.61656(2) 0.02772(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.871(2) . ?
S1 O2 1.4311(17) . ?
S1 O3 1.4328(16) . ?
S1 C8 1.757(2) . ?
F1 C1 1.365(2) . ?
O1 C2 1.206(3) . ?
C1 S2 1.878(2) . ?
C1 C2 1.551(3) . ?
S2 O4 1.4314(17) . ?
S2 O5 1.4354(17) . ?
S2 C14 1.751(2) . ?
C2 C3 1.489(3) . ?
C3 C4 1.406(3) . ?
C3 C7 1.402(3) . ?
C4 C5 1.391(3) . ?
C4 Br1 1.896(2) . ?
C5 C6 1.383(4) . ?
C6 C00P 1.387(3) . ?
C7 C00P 1.387(3) . ?
C8 C9 1.396(3) . ?
C8 C13 1.397(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.388(3) . ?
C14 C15 1.388(3) . ?
C14 C19 1.389(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.388(3) . ?
C18 C19 1.392(3) . ?

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
O2 S1 C1 108.78(9) . . ?
O2 S1 O3 120.37(10) . . ?
O2 S1 C8 109.95(10) . . ?
O3 S1 C1 103.44(9) . . ?
O3 S1 C8 108.64(10) . . ?
C8 S1 C1 104.35(10) . . ?
S1 C1 S2 111.82(11) . . ?
F1 C1 S1 104.74(13) . . ?
F1 C1 S2 106.70(13) . . ?
F1 C1 C2 113.95(17) . . ?
C2 C1 S1 111.88(14) . . ?
C2 C1 S2 107.70(14) . . ?
O4 S2 C1 107.21(10) . . ?
O4 S2 O5 120.75(11) . . ?
O4 S2 C14 110.32(10) . . ?
O5 S2 C1 102.95(10) . . ?
O5 S2 C14 109.03(10) . . ?
C14 S2 C1 105.26(9) . . ?
O1 C2 C1 115.64(19) . . ?
O1 C2 C3 124.3(2) . . ?
C3 C2 C1 120.07(18) . . ?
C4 C3 C2 121.2(2) . . ?
C7 C3 C2 120.70(19) . . ?
C7 C3 C4 117.9(2) . . ?
C3 C4 Br1 123.18(17) . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 Br1 116.33(17) . . ?
C6 C5 C4 120.6(2) . . ?
C5 C6 C00P 120.0(2) . . ?
C00P C7 C3 121.4(2) . . ?
C9 C8 S1 118.79(17) . . ?
C9 C8 C13 122.0(2) . . ?
C13 C8 S1 119.11(17) . . ?
C10 C9 C8 118.8(2) . . ?
C9 C10 C11 119.8(2) . . ?
C10 C11 C12 120.9(2) . . ?
C13 C12 C11 120.3(2) . . ?
C12 C13 C8 118.1(2) . . ?
C15 C14 S2 118.37(17) . . ?
C15 C14 C19 122.8(2) . . ?
C19 C14 S2 118.83(16) . . ?
C14 C15 C16 118.3(2) . . ?
C15 C16 C17 119.9(2) . . ?
C18 C17 C16 120.9(2) . . ?
C17 C18 C19 120.1(2) . . ?
C14 C19 C18 118.0(2) . . ?
C7 C00P C6 119.8(2) . . ?

_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 1.367
_oxdiff_exptl_absorpt_empirical_full_min 0.664
####################################################################### 
# 
# 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_final_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2427874'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 Cl F O5 S3'
_chemical_formula_sum            'C22 H14 Cl F O5 S3'
_chemical_formula_weight         508.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S3O5ClF
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'
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'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.9595(2)
_cell_length_b                   7.98710(10)
_cell_length_c                   31.2605(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.0410(10)
_cell_angle_gamma                90
_cell_volume                     4233.76(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13087
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2510
_cell_measurement_theta_min      2.8130
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.259
_exptl_absorpt_coefficient_mu    4.753
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.278
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (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 green'
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 -2 0.0532
2 1 2 0.1215
-2 1 0 0.1360
1 -2 2 0.1900
-1 1 -1 0.0972
0 0 1 0.0600
0 0 -1 0.0120
1 0 0 0.1892

_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.072
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
-2.0028 -0.9995 -1.9868 0.2479 -0.0967 0.0982
2.0028 0.9995 1.9868 -0.2479 0.0967 -0.0982
-1.9982 1.0000 0.0060 -0.1169 -0.0190 0.2371
0.9983 -1.9986 2.0004 0.3252 0.1233 -0.2145
-0.9991 0.9995 -0.9980 -0.1467 -0.0638 0.1498
0.0008 0.0003 0.9994 -0.0020 0.0492 0.0023
-0.0008 -0.0003 -0.9994 0.0020 -0.0492 -0.0023
0.9999 -0.0003 -0.0045 -0.0318 0.0043 -0.0850

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            17582
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.989
_diffrn_reflns_theta_min         2.828
_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 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  73.00   0.50    0.25    --  111.50 -95.00-180.00   64
  2  ω     -6.00  60.00   0.50    0.10    --   49.66 -97.00 -50.00  132
  3  ω     82.00 111.00   0.50    0.25    --  111.50-125.00  60.00   58
  4  ω     43.00  84.00   0.50    0.25    --  111.50-125.00  30.00   82
  5  ω     46.00  99.00   0.50    0.25    --  111.50 -97.00 -50.00  106
  6  ω     78.00 106.00   0.50    0.25    --  111.50 -77.00 -30.00   56
  7  ω     41.00  70.00   0.50    0.25    --  111.50 -61.00  90.00   58
  8  ω     45.00  71.00   0.50    0.25    --  111.50 -77.00 -30.00   52
  9  ω     44.00  69.00   0.50    0.25    --  111.50 -61.00  30.00   50
 10  ω     42.00  67.00   0.50    0.25    --  111.50 -61.00   0.00   50
 11  ω     43.00  69.00   0.50    0.25    --  111.50 -61.00 -30.00   52
 12  ω     43.00  68.00   0.50    0.25    --  111.50 -61.00 -60.00   50
 13  ω     41.00  66.00   0.50    0.25    --  111.50 -61.00-120.00   50
 14  ω     41.00  72.00   0.50    0.25    --  111.50 -61.00-150.00   62
 15  ω     47.00  72.00   0.50    0.25    --  111.50 -61.00-180.00   50
 16  ω     42.00  70.00   0.50    0.25    --  111.50 -61.00 150.00   56
 17  ω    102.00 131.00   0.50    0.25    --  111.50  45.00  90.00   58
 18  ω    142.00 168.00   0.50    0.25    --  111.50  45.00  90.00   52
 19  ω    102.00 172.00   0.50    0.25    --  111.50  45.00  30.00  140
 20  ω    129.00 176.00   0.50    0.25    --  111.50  15.00 -30.00   94
 21  ω    110.00 154.00   0.50    0.25    --  111.50  97.00  56.00   88
 22  ω     95.00 124.00   0.50    0.25    --  111.50 125.00-180.00   58
 23  ω    135.00 177.00   0.50    0.25    --  111.50 125.00-180.00   84
 24  ω    -25.00  24.00   0.50    0.10    --  -49.66  19.00  90.00   98
 25  ω    -68.00 -42.00   0.50    0.25    --  -90.00  61.00  60.00   52
 26  ω    -49.00 -24.00   0.50    0.25    --  -90.00  45.00-120.00   50
 27  ω    -25.00  24.00   0.50    0.10    --  -49.66  19.00-180.00   98
 28  ω   -116.00 -85.00   0.50    0.10    --  -49.66 -57.00 -60.00   62
 29  ω   -124.00 -98.00   0.50    0.25    --  -90.00 -97.00 -50.00   52
 30  ω   -117.00 -88.00   0.50    0.10    --  -49.66-125.00  90.00   58
 31  ω   -154.00-117.00   0.50    0.25    --  -90.00 -95.00  30.00   74
 32  ω    -74.00 -49.00   0.50    0.25    --  -90.00  97.00  56.00   50
 33  ω    -79.00 -44.00   0.50    0.10    --  -49.66  97.00  56.00   70
 34  ω    -15.00  19.00   0.50    0.10    --  -49.66  97.00  56.00   68
;
_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      -0.0318220000
_diffrn_orient_matrix_UB_12      -0.1804836000
_diffrn_orient_matrix_UB_13      -0.0018864000
_diffrn_orient_matrix_UB_21      0.0045596000
_diffrn_orient_matrix_UB_22      -0.0101899000
_diffrn_orient_matrix_UB_23      0.0491934000
_diffrn_orient_matrix_UB_31      -0.0849755000
_diffrn_orient_matrix_UB_32      0.0672904000
_diffrn_orient_matrix_UB_33      0.0023914000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4220
_reflns_number_total             4459
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+4.4242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_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
F1 F 0.25746(5) 0.45284(11) 0.59012(3) 0.01768(18) Uani 1 1 d . . . . .
O1 O 0.16069(6) 0.28538(14) 0.67896(3) 0.0208(2) Uani 1 1 d . . . . .
C1 C 0.20182(8) 0.35850(18) 0.61057(5) 0.0159(3) Uani 1 1 d . . . . .
S2 S 0.20873(2) 0.14524(4) 0.58774(2) 0.01661(10) Uani 1 1 d . . . . .
O2 O 0.04594(6) 0.32960(16) 0.59635(4) 0.0260(3) Uani 1 1 d . . . . .
C2 C 0.21192(8) 0.35752(19) 0.65968(5) 0.0170(3) Uani 1 1 d . . . . .
S3 S 0.10421(2) 0.45885(5) 0.59816(2) 0.01898(10) Uani 1 1 d . . . . .
O3 O 0.09898(7) 0.59114(16) 0.62897(4) 0.0287(3) Uani 1 1 d . . . . .
C3 C 0.27854(8) 0.44376(19) 0.68058(5) 0.0173(3) Uani 1 1 d . . . . .
O4 O 0.19297(7) 0.16491(15) 0.54277(4) 0.0238(2) Uani 1 1 d . . . . .
C4 C 0.28097(9) 0.48970(19) 0.72294(5) 0.0179(3) Uani 1 1 d . . . . .
O5 O 0.16210(6) 0.03491(14) 0.61290(4) 0.0235(2) Uani 1 1 d . . . . .
C5 C 0.35339(9) 0.56587(19) 0.73663(5) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.37595(9) 0.6278(2) 0.77726(5) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.340898 0.621613 0.800567 0.027 Uiso 1 1 calc R U . . .
C7 C 0.44975(9) 0.6973(2) 0.78251(5) 0.0240(3) Uani 1 1 d . . . . .
H7 H 0.465441 0.740802 0.809632 0.029 Uiso 1 1 calc R U . . .
C8 C 0.50219(9) 0.7048(2) 0.74828(5) 0.0230(3) Uani 1 1 d . . . . .
H8 H 0.552839 0.753100 0.752800 0.028 Uiso 1 1 calc R U . . .
C9 C 0.48203(9) 0.6438(2) 0.70829(5) 0.0217(3) Uani 1 1 d . . . . .
H9 H 0.517887 0.648582 0.685323 0.026 Uiso 1 1 calc R U . . .
C10 C 0.40658(9) 0.57447(19) 0.70282(5) 0.0182(3) Uani 1 1 d . . . . .
C11 C 0.30877(8) 0.09910(19) 0.59624(5) 0.0170(3) Uani 1 1 d . . . . .
C12 C 0.33177(10) 0.0228(2) 0.63459(5) 0.0227(3) Uani 1 1 d . . . . .
H12 H 0.293842 -0.007572 0.655197 0.027 Uiso 1 1 calc R U . . .
C13 C 0.41125(11) -0.0078(2) 0.64189(6) 0.0301(4) Uani 1 1 d . . . . .
H13 H 0.428412 -0.057944 0.667998 0.036 Uiso 1 1 calc R U . . .
C14 C 0.46597(10) 0.0346(2) 0.61122(7) 0.0327(4) Uani 1 1 d . . . . .
H14 H 0.520429 0.013864 0.616527 0.039 Uiso 1 1 calc R U . . .
C15 C 0.44160(10) 0.1071(2) 0.57285(6) 0.0291(4) Uani 1 1 d . . . . .
H15 H 0.479421 0.133922 0.551872 0.035 Uiso 1 1 calc R U . . .
C16 C 0.36258(9) 0.1408(2) 0.56493(5) 0.0217(3) Uani 1 1 d . . . . .
H16 H 0.345579 0.190950 0.538805 0.026 Uiso 1 1 calc R U . . .
C17 C 0.11610(9) 0.5488(2) 0.54717(5) 0.0187(3) Uani 1 1 d . . . . .
C18 C 0.09392(9) 0.4583(2) 0.51096(5) 0.0194(3) Uani 1 1 d . . . . .
H18 H 0.075482 0.346448 0.513266 0.023 Uiso 1 1 calc R U . . .
C19 C 0.09936(9) 0.5356(2) 0.47124(5) 0.0217(3) Uani 1 1 d . . . . .
H19 H 0.084553 0.476207 0.446018 0.026 Uiso 1 1 calc R U . . .
C20 C 0.12633(10) 0.6988(2) 0.46838(5) 0.0263(3) Uani 1 1 d . . . . .
H20 H 0.129966 0.750804 0.441147 0.032 Uiso 1 1 calc R U . . .
C21 C 0.14805(12) 0.7871(2) 0.50495(6) 0.0316(4) Uani 1 1 d . . . . .
H21 H 0.166418 0.899016 0.502651 0.038 Uiso 1 1 calc R U . . .
C22 C 0.14303(11) 0.7122(2) 0.54499(5) 0.0266(3) Uani 1 1 d . . . . .
H22 H 0.157716 0.771722 0.570214 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.20458(2) 0.46648(5) 0.75751(2) 0.02410(10) Uani 1 1 d . . . . .
S1 S 0.36703(2) 0.49482(5) 0.65555(2) 0.02094(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3744(16) . ?
O1 C2 1.2119(18) . ?
C1 S2 1.8514(15) . ?
C1 C2 1.542(2) . ?
C1 S3 1.8734(15) . ?
S2 O4 1.4347(11) . ?
S2 O5 1.4294(12) . ?
S2 C11 1.7517(14) . ?
O2 S3 1.4296(12) . ?
C2 C3 1.467(2) . ?
S3 O3 1.4337(13) . ?
S3 C17 1.7632(16) . ?
C3 C4 1.374(2) . ?
C3 S1 1.7531(15) . ?
C4 C5 1.429(2) . ?
C4 Cl1 1.7124(15) . ?
C5 C6 1.409(2) . ?
C5 C10 1.404(2) . ?
C6 C7 1.376(2) . ?
C7 C8 1.405(2) . ?
C8 C9 1.379(2) . ?
C9 C10 1.402(2) . ?
C10 S1 1.7326(15) . ?
C11 C12 1.394(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.385(2) . ?
C13 C14 1.388(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.385(2) . ?
C17 C18 1.389(2) . ?
C17 C22 1.385(2) . ?
C18 C19 1.391(2) . ?
C19 C20 1.385(2) . ?
C20 C21 1.387(3) . ?
C21 C22 1.391(2) . ?

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
F1 C1 S2 106.03(9) . . ?
F1 C1 C2 113.66(11) . . ?
F1 C1 S3 106.29(9) . . ?
S2 C1 S3 112.07(7) . . ?
C2 C1 S2 111.88(10) . . ?
C2 C1 S3 106.87(9) . . ?
O4 S2 C1 105.37(7) . . ?
O4 S2 C11 109.53(7) . . ?
O5 S2 C1 108.39(7) . . ?
O5 S2 O4 120.76(7) . . ?
O5 S2 C11 109.32(7) . . ?
C11 S2 C1 101.71(7) . . ?
O1 C2 C1 115.46(13) . . ?
O1 C2 C3 123.73(14) . . ?
C3 C2 C1 120.79(13) . . ?
O2 S3 C1 107.86(7) . . ?
O2 S3 O3 120.50(8) . . ?
O2 S3 C17 110.41(7) . . ?
O3 S3 C1 103.97(7) . . ?
O3 S3 C17 108.47(8) . . ?
C17 S3 C1 104.27(7) . . ?
C2 C3 S1 124.70(11) . . ?
C4 C3 C2 124.34(14) . . ?
C4 C3 S1 110.92(11) . . ?
C3 C4 C5 114.39(14) . . ?
C3 C4 Cl1 124.72(12) . . ?
C5 C4 Cl1 120.86(12) . . ?
C6 C5 C4 129.57(14) . . ?
C10 C5 C4 110.84(13) . . ?
C10 C5 C6 119.59(14) . . ?
C7 C6 C5 118.71(15) . . ?
C6 C7 C8 120.88(15) . . ?
C9 C8 C7 121.70(14) . . ?
C8 C9 C10 117.44(14) . . ?
C5 C10 S1 112.34(11) . . ?
C9 C10 C5 121.68(14) . . ?
C9 C10 S1 125.97(12) . . ?
C12 C11 S2 118.52(12) . . ?
C16 C11 S2 119.29(12) . . ?
C16 C11 C12 122.20(14) . . ?
C13 C12 C11 118.36(16) . . ?
C12 C13 C14 120.27(17) . . ?
C15 C14 C13 120.42(16) . . ?
C16 C15 C14 120.48(16) . . ?
C15 C16 C11 118.25(15) . . ?
C18 C17 S3 119.42(12) . . ?
C22 C17 S3 118.13(12) . . ?
C22 C17 C18 122.33(15) . . ?
C17 C18 C19 118.39(15) . . ?
C20 C19 C18 120.17(15) . . ?
C19 C20 C21 120.52(15) . . ?
C20 C21 C22 120.24(17) . . ?
C17 C22 C21 118.35(16) . . ?
C10 S1 C3 91.49(7) . . ?

_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.711
####################################################################### 
# 
# 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_final_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2427877'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C28 H21 F O6 S2)'
_chemical_formula_sum            'C112 H84 F4 O24 S8'
_chemical_formula_weight         2146.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O6F
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'
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'
F F 0.0727 0.0534 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1826(2)
_cell_length_b                   7.7862(2)
_cell_length_c                   37.8984(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.370(2)
_cell_angle_gamma                90
_cell_volume                     2413.87(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    10815
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.4360
_cell_measurement_theta_min      2.3450
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.627
_exptl_absorpt_coefficient_mu    2.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 -2 0.0738
0 0 -1 0.0166
0 0 1 0.0492
-2 1 2 0.1235
2 -1 -2 0.0734
1 2 -2 0.0165
-1 -2 2 0.0621
0 -2 -1 0.0544
-2 -1 2 0.0935
-2 -2 -1 0.0860
1 0 2 0.0680
-1 0 -2 0.1145
1 1 -2 0.0161

_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.07
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
1.0027 -0.9966 -2.0000 0.0726 0.1391 0.2357
-0.0002 -0.0002 -0.9987 -0.0329 -0.0006 0.0238
0.0002 0.0002 0.9987 0.0329 0.0006 -0.0238
-2.0028 0.9936 2.0045 -0.1832 -0.0888 -0.3797
2.0028 -0.9936 -2.0045 0.1832 0.0888 0.3797
0.9941 2.0012 -2.0053 -0.0111 -0.4330 0.1030
-0.9926 -2.0038 2.0160 0.0117 0.4334 -0.1029
0.0050 -2.0007 -0.9942 0.0229 0.3812 0.1123
-1.9946 -1.0068 2.0211 -0.1266 0.2928 -0.2910
-1.9934 -2.0072 -0.9776 -0.1977 0.4818 -0.1755
1.0008 0.0046 1.9916 0.1763 -0.0493 0.0964
-1.0008 -0.0046 -1.9916 -0.1763 0.0493 -0.0964
0.9951 1.0044 -2.0049 0.0165 -0.2427 0.1469

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            19456
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         80.242
_diffrn_reflns_theta_min         2.332
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -14.00   0.50    0.50    --  -49.66 109.00 -50.00  132
  2  ω     24.00  62.00   0.50    0.50    --   49.66-109.00-146.00   76
  3  ω   -133.00 -97.00   0.50    2.00    --  -90.00-109.00-146.00   72
  4  ω    -76.00 -51.00   0.50    2.00    --  -90.00 109.00 -50.00   50
  5  ω     82.00 108.00   0.50    2.00    --  111.50-109.00-146.00   52
  6  ω    104.00 178.00   0.50    2.00    --  111.50 109.00 -50.00  148
  7  ω   -116.00 -91.00   0.50    0.50    --  -49.66 -57.00-180.00   50
  8  ω   -119.00 -83.00   0.50    0.50    --  -49.66 -57.00-150.00   72
  9  ω   -111.00 -84.00   0.50    0.50    --  -49.66 -57.00 -90.00   54
 10  ω   -114.00 -88.00   0.50    0.50    --  -49.66-125.00 120.00   52
 11  ω   -116.00 -90.00   0.50    0.50    --  -49.66-125.00  90.00   52
 12  ω   -119.00 -82.00   0.50    0.50    --  -49.66 -57.00 150.00   74
 13  ω    -48.00 -20.00   0.50    2.00    --  -90.00  45.00 -90.00   56
 14  ω    -50.00 -20.00   0.50    2.00    --  -90.00  45.00 150.00   60
 15  ω    103.00 175.00   0.50    2.00    --  111.50  45.00-150.00  144
 16  ω     46.00  71.00   0.50    2.00    --  111.50 -61.00  60.00   50
 17  ω     42.00  68.00   0.50    2.00    --  111.50 -61.00-120.00   52
 18  ω     96.00 137.00   0.50    2.00    --  111.50 125.00  90.00   82
 19  ω    143.00 176.00   0.50    2.00    --  111.50 125.00  90.00   66
 20  ω     45.00  70.00   0.50    2.00    --  111.50 -95.00-120.00   50
 21  ω     41.00  71.00   0.50    2.00    --  111.50 -61.00   0.00   60
 22  ω     59.00  98.00   0.50    2.00    --  111.50 -95.00 120.00   78
 23  ω     42.00  67.00   0.50    2.00    --  111.50 -61.00 -90.00   50
 24  ω     76.00 101.00   0.50    2.00    --  111.50 -77.00-120.00   50
 25  ω    150.00 176.00   0.50    2.00    --  111.50  15.00  60.00   52
 26  ω    106.00 132.00   0.50    2.00    --  111.50  15.00  60.00   52
 27  ω     47.00  72.00   0.50    2.00    --  111.50 -77.00-120.00   50
 28  ω     80.00 105.00   0.50    2.00    --  111.50 -95.00-120.00   50
 29  ω     83.00 108.00   0.50    2.00    --  111.50-125.00 -90.00   50
 30  ω     41.00  69.00   0.50    2.00    --  111.50 -61.00 -30.00   56
 31  ω    106.00 162.00   0.50    2.00    --  111.50  30.00 -60.00  112
 32  ω     79.00 104.00   0.50    2.00    --  111.50 -95.00 -90.00   50
 33  ω     46.00  71.00   0.50    2.00    --  111.50-125.00  30.00   50
 34  ω     86.00 111.00   0.50    2.00    --  111.50-125.00  30.00   50
 35  ω     47.00  72.00   0.50    2.00    --  111.50 -61.00  30.00   50
;
_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      0.1107704000
_diffrn_orient_matrix_UB_12      -0.0275488000
_diffrn_orient_matrix_UB_13      0.0329384000
_diffrn_orient_matrix_UB_21      -0.0497114000
_diffrn_orient_matrix_UB_22      -0.1909875000
_diffrn_orient_matrix_UB_23      0.0006836000
_diffrn_orient_matrix_UB_31      0.1439403000
_diffrn_orient_matrix_UB_32      -0.0439092000
_diffrn_orient_matrix_UB_33      -0.0238248000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4547
_reflns_number_total             5165
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5165
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.087
_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)+(0.0545P)²+1.4546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C27) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C26) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C25) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_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
S1 S 0.04875(5) 0.38478(6) 0.56769(2) 0.01890(12) Uani 1 1 d . . . . .
F1 F 0.31957(12) 0.47128(15) 0.60034(3) 0.0216(2) Uani 1 1 d . . . . .
O1 O 0.24680(15) 0.35185(18) 0.66092(3) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.2196(2) 0.3303(3) 0.59893(5) 0.0186(4) Uani 1 1 d . . . . .
S2 S 0.34858(5) 0.14710(6) 0.58425(2) 0.01910(12) Uani 1 1 d . . . . .
O2 O 0.03950(16) 0.19081(19) 0.63876(3) 0.0236(3) Uani 1 1 d . . . . .
C2 C 0.1557(2) 0.2824(2) 0.63543(5) 0.0176(3) Uani 1 1 d . . . . .
O3 O 0.12572(16) 0.4673(2) 0.53875(3) 0.0256(3) Uani 1 1 d . . . . .
C3 C 0.1963(2) 0.3065(3) 0.69661(4) 0.0180(4) Uani 1 1 d . . . . .
H3A H 0.194422 0.180205 0.699534 0.022 Uiso 1 1 calc R U . . .
H3B H 0.085548 0.351824 0.700977 0.022 Uiso 1 1 calc R U . . .
O4 O -0.04693(16) 0.23314(19) 0.56241(4) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.3200(2) 0.3863(2) 0.72213(5) 0.0172(3) Uani 1 1 d . . . . .
H4 H 0.326930 0.512292 0.717283 0.021 Uiso 1 1 calc R U . . .
O5 O 0.48861(17) 0.1576(2) 0.60761(4) 0.0300(3) Uani 1 1 d . . . . .
C5 C 0.2729(2) 0.3598(2) 0.76036(5) 0.0177(4) Uani 1 1 d . . . . .
O6 O 0.24709(18) -0.0014(2) 0.58436(5) 0.0332(4) Uani 1 1 d . . . . .
C6 C 0.1253(2) 0.3916(2) 0.77634(5) 0.0199(4) Uani 1 1 d . . . . .
H6 H 0.033894 0.433193 0.762983 0.024 Uiso 1 1 calc R U . . .
C7 C 0.1141(2) 0.3612(3) 0.81244(5) 0.0244(4) Uani 1 1 d . . . . .
H7 H 0.013617 0.382029 0.823740 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2479(3) 0.3008(3) 0.83227(5) 0.0255(4) Uani 1 1 d . . . . .
H8 H 0.238494 0.283787 0.856959 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3948(2) 0.2653(3) 0.81618(5) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.485413 0.222082 0.829558 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4068(2) 0.2941(2) 0.78000(5) 0.0187(4) Uani 1 1 d . . . . .
C11 C 0.5417(2) 0.2623(2) 0.75606(5) 0.0188(4) Uani 1 1 d . . . . .
C12 C 0.6956(2) 0.1916(3) 0.76257(5) 0.0231(4) Uani 1 1 d . . . . .
H12 H 0.730676 0.161772 0.785853 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7969(2) 0.1659(3) 0.73408(6) 0.0257(4) Uani 1 1 d . . . . .
H13 H 0.902507 0.117831 0.737984 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7459(2) 0.2093(3) 0.70003(6) 0.0250(4) Uani 1 1 d . . . . .
H14 H 0.816118 0.188265 0.680901 0.030 Uiso 1 1 calc R U . . .
C15 C 0.5922(2) 0.2837(3) 0.69352(5) 0.0216(4) Uani 1 1 d . . . . .
H15 H 0.558130 0.315261 0.670271 0.026 Uiso 1 1 calc R U . . .
C16 C 0.4913(2) 0.3102(2) 0.72185(5) 0.0185(4) Uani 1 1 d . . . . .
C17 C -0.0644(2) 0.5404(3) 0.59043(5) 0.0201(4) Uani 1 1 d . . . . .
C18 C -0.0192(2) 0.7119(3) 0.58659(5) 0.0212(4) Uani 1 1 d . . . . .
H18 H 0.074897 0.741790 0.573740 0.025 Uiso 1 1 calc R U . . .
C19 C -0.1140(2) 0.8381(3) 0.60185(5) 0.0232(4) Uani 1 1 d . . . . .
H19 H -0.084471 0.955581 0.599733 0.028 Uiso 1 1 calc R U . . .
C20 C -0.2527(2) 0.7922(3) 0.62031(5) 0.0241(4) Uani 1 1 d . . . . .
H20 H -0.318925 0.878912 0.630279 0.029 Uiso 1 1 calc R U . . .
C21 C -0.2949(2) 0.6200(3) 0.62423(5) 0.0252(4) Uani 1 1 d . . . . .
H21 H -0.389256 0.590276 0.637027 0.030 Uiso 1 1 calc R U . . .
C22 C -0.2006(2) 0.4916(3) 0.60965(5) 0.0231(4) Uani 1 1 d . . . . .
H22 H -0.227601 0.373921 0.612631 0.028 Uiso 1 1 calc R U . . .
C23 C 0.4066(2) 0.1943(3) 0.54126(5) 0.0225(4) Uani 1 1 d . . . . .
C24 C 0.5526(3) 0.2805(3) 0.53655(7) 0.0373(5) Uani 1 1 d . . . . .
H24 H 0.616899 0.318185 0.556271 0.045 Uiso 1 1 calc R U . . .
C25 C 0.6027(5) 0.3104(4) 0.50259(9) 0.0627(10) Uani 1 1 d . U . . .
H25 H 0.702761 0.368787 0.498844 0.075 Uiso 1 1 calc R U . . .
C26 C 0.5100(5) 0.2570(4) 0.47445(8) 0.0668(11) Uani 1 1 d . U . . .
H26 H 0.545754 0.278608 0.451208 0.080 Uiso 1 1 calc R U . . .
C27 C 0.3641(5) 0.1716(5) 0.47929(7) 0.0637(11) Uani 1 1 d . U . . .
H27 H 0.300135 0.135992 0.459351 0.076 Uiso 1 1 calc R U . . .
C28 C 0.3099(3) 0.1372(4) 0.51320(6) 0.0389(6) Uani 1 1 d . . . . .
H28 H 0.210675 0.077090 0.516864 0.047 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
S1 C1 1.8592(18) . ?
S1 O3 1.4303(14) . ?
S1 O4 1.4282(15) . ?
S1 C17 1.763(2) . ?
F1 C1 1.369(2) . ?
O1 C2 1.322(2) . ?
O1 C3 1.467(2) . ?
C1 S2 1.8672(19) . ?
C1 C2 1.536(2) . ?
S2 O5 1.4335(15) . ?
S2 O6 1.4239(16) . ?
S2 C23 1.7467(19) . ?
O2 C2 1.198(2) . ?
C3 C4 1.516(2) . ?
C4 C5 1.522(2) . ?
C4 C16 1.522(2) . ?
C5 C6 1.387(3) . ?
C5 C10 1.406(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.395(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.395(3) . ?
C10 C11 1.466(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.402(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.401(3) . ?
C15 C16 1.386(3) . ?
C17 C18 1.394(3) . ?
C17 C22 1.398(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.394(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.386(3) . ?
C23 C24 1.386(3) . ?
C23 C28 1.384(3) . ?
C24 C25 1.380(3) . ?
C25 C26 1.359(6) . ?
C26 C27 1.383(6) . ?
C27 C28 1.395(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
O3 S1 C1 104.63(8) . . ?
O3 S1 C17 108.19(9) . . ?
O4 S1 C1 107.58(9) . . ?
O4 S1 O3 120.92(9) . . ?
O4 S1 C17 110.14(9) . . ?
C17 S1 C1 103.97(8) . . ?
C2 O1 C3 114.17(14) . . ?
S1 C1 S2 113.97(10) . . ?
F1 C1 S1 106.34(12) . . ?
F1 C1 S2 106.42(11) . . ?
F1 C1 C2 112.04(15) . . ?
C2 C1 S1 111.20(12) . . ?
C2 C1 S2 106.86(13) . . ?
O5 S2 C1 102.80(9) . . ?
O5 S2 C23 109.46(9) . . ?
O6 S2 C1 106.60(9) . . ?
O6 S2 O5 120.13(10) . . ?
O6 S2 C23 110.20(10) . . ?
C23 S2 C1 106.59(9) . . ?
O1 C2 C1 111.15(15) . . ?
O2 C2 O1 126.98(16) . . ?
O2 C2 C1 121.85(16) . . ?
O1 C3 C4 106.92(14) . . ?
C3 C4 C5 111.79(14) . . ?
C3 C4 C16 115.92(15) . . ?
C16 C4 C5 102.01(14) . . ?
C6 C5 C4 129.39(17) . . ?
C6 C5 C10 120.64(17) . . ?
C10 C5 C4 109.98(15) . . ?
C5 C6 C7 118.49(18) . . ?
C6 C7 C8 121.12(18) . . ?
C9 C8 C7 120.47(18) . . ?
C8 C9 C10 118.80(18) . . ?
C5 C10 C11 108.80(16) . . ?
C9 C10 C5 120.44(17) . . ?
C9 C10 C11 130.73(17) . . ?
C12 C11 C10 130.45(18) . . ?
C12 C11 C16 120.95(17) . . ?
C16 C11 C10 108.56(15) . . ?
C13 C12 C11 118.22(18) . . ?
C14 C13 C12 120.99(17) . . ?
C13 C14 C15 120.86(18) . . ?
C16 C15 C14 118.30(18) . . ?
C11 C16 C4 110.34(15) . . ?
C15 C16 C4 129.02(17) . . ?
C15 C16 C11 120.64(17) . . ?
C18 C17 S1 117.62(14) . . ?
C18 C17 C22 122.12(18) . . ?
C22 C17 S1 120.14(16) . . ?
C19 C18 C17 118.86(18) . . ?
C18 C19 C20 119.85(19) . . ?
C21 C20 C19 120.48(19) . . ?
C22 C21 C20 120.63(18) . . ?
C21 C22 C17 118.03(19) . . ?
C24 C23 S2 118.45(17) . . ?
C28 C23 S2 119.09(18) . . ?
C28 C23 C24 122.4(2) . . ?
C25 C24 C23 118.6(3) . . ?
C26 C25 C24 120.5(3) . . ?
C25 C26 C27 120.7(2) . . ?
C26 C27 C28 120.6(3) . . ?
C23 C28 C27 117.2(3) . . ?

_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 1.807
_oxdiff_exptl_absorpt_empirical_full_min 0.242
####################################################################### 
# 
# 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_final_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2427878'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 F O5 S2'
_chemical_formula_sum            'C24 H23 F O5 S2'
_chemical_formula_weight         474.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O5F
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2701(3)
_cell_length_b                   8.3246(3)
_cell_length_c                   17.3376(7)
_cell_angle_alpha                98.003(3)
_cell_angle_beta                 101.714(3)
_cell_angle_gamma                104.485(3)
_cell_volume                     1108.66(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10880
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.8990
_cell_measurement_theta_min      2.6430
_shelx_estimated_absorpt_T_max   0.743
_shelx_estimated_absorpt_T_min   0.561
_exptl_absorpt_coefficient_mu    2.549
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 2 0.0950
0 -2 1 0.0844
-2 2 1 0.1069
1 0 -1 0.0709
1 0 1 0.0510
-1 0 -1 0.0733
-1 1 -2 0.0597
1 -1 2 0.0881
-1 0 2 0.0620
1 0 -2 0.0709
1 -1 -2 0.0556

_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.124
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
-2.0000 1.0009 1.9989 0.1214 -0.2337 -0.3071
0.0000 -1.9999 1.0007 0.1046 -0.2020 0.3075
-2.0000 2.0009 0.9984 0.1018 -0.1008 -0.4532
1.0000 -0.0005 -0.9995 -0.1032 0.1514 0.0728
1.0000 -0.0004 1.0009 -0.2341 0.0239 0.0423
-1.0000 0.0004 -1.0009 0.2341 -0.0239 -0.0423
-1.0001 1.0003 -2.0014 0.2145 0.1090 -0.1884
1.0001 -1.0003 2.0014 -0.2145 -0.1090 0.1884
-1.0000 0.0005 1.9998 0.0378 -0.2152 -0.0881
1.0000 -0.0005 -1.9998 -0.0378 0.2152 0.0881
1.0000 -1.0005 -1.9995 0.0473 0.1461 0.2495

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16972
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.967
_diffrn_reflns_theta_min         2.657
_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 0.997
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  91.00   0.50    0.20    --   49.53-125.00 150.00  114
  2  ω     87.00 113.00   0.50    0.20    --   49.53-169.00  35.00   52
  3  ω    104.00 143.00   0.50    0.75    --  111.50-169.00  35.00   78
  4  ω     48.00  88.00   0.50    0.75    --  111.50-125.00 150.00   80
  5  ω     56.00 110.00   0.50    0.75    --  111.50-125.00 -60.00  108
  6  ω     75.00 105.00   0.50    0.75    --  111.50 -95.00-120.00   60
  7  ω     54.00 106.00   0.50    0.75    --  111.50-125.00-180.00  104
  8  ω     82.00 109.00   0.50    0.75    --  111.50-115.00-179.00   54
  9  ω     53.00  78.00   0.50    0.75    --  111.50-115.00-179.00   50
 10  ω     43.00  68.00   0.50    0.75    --  111.50 -95.00-180.00   50
 11  ω     73.00 103.00   0.50    0.75    --  111.50 -95.00-180.00   60
 12  ω     39.00  76.00   0.50    0.20    --   49.53-115.00-179.00   74
 13  ω     79.00 105.00   0.50    0.75    --  111.50 -95.00 -30.00   52
 14  ω     44.00  72.00   0.50    0.75    --  111.50 -95.00 -30.00   56
 15  ω     44.00  72.00   0.50    0.75    --  111.50 -95.00   0.00   56
 16  ω     76.00 105.00   0.50    0.75    --  111.50 -95.00   0.00   58
 17  ω     61.00 104.00   0.50    0.75    --  111.50 -95.00  30.00   86
 18  ω     43.00  73.00   0.50    0.75    --  111.50 -95.00  90.00   60
 19  ω     55.00 104.00   0.50    0.75    --  111.50 -95.00  60.00   98
 20  ω     79.00 104.00   0.50    0.75    --  111.50 -95.00 -90.00   50
 21  ω     43.00  90.00   0.50    0.75    --  111.50 -77.00-180.00   94
 22  ω     44.00  92.00   0.50    0.75    --  111.50 -77.00-150.00   96
 23  ω     41.00  67.00   0.50    0.75    --  111.50 -61.00-120.00   52
 24  ω     41.00  66.00   0.50    0.75    --  111.50 -61.00-180.00   50
 25  ω     44.00  69.00   0.50    0.75    --  111.50 -61.00 -90.00   50
 26  ω     47.00  72.00   0.50    0.75    --  111.50 -61.00 -30.00   50
 27  ω     47.00  72.00   0.50    0.75    --  111.50 -61.00   0.00   50
 28  ω     41.00  68.00   0.50    0.75    --  111.50 -61.00  30.00   54
 29  ω     44.00  69.00   0.50    0.75    --  111.50 -61.00  60.00   50
 30  ω   -114.00 -85.00   0.50    0.20    --  -49.53 -57.00  60.00   58
 31  ω   -117.00 -84.00   0.50    0.20    --  -49.53 -57.00 150.00   66
 32  ω   -117.00 -86.00   0.50    0.20    --  -49.53 -57.00  30.00   62
 33  ω   -119.00 -83.00   0.50    0.20    --  -49.53 -57.00 -30.00   72
 34  ω   -120.00 -86.00   0.50    0.20    --  -49.53 -57.00 -90.00   68
 35  ω   -135.00 -81.00   0.50    0.75    --  -90.00 -45.00-120.00  108
 36  ω   -119.00 -94.00   0.50    0.75    --  -90.00-115.00-179.00   50
 37  ω   -116.00 -86.00   0.50    0.20    --  -49.53-169.00  35.00   60
 38  ω    -81.00 -45.00   0.50    0.20    --  -49.53-169.00  35.00   72
 39  ω   -114.00 -89.00   0.50    0.75    --  -90.00-169.00  35.00   50
 40  ω    -24.00  19.00   0.50    0.20    --  -49.53  19.00  30.00   86
 41  ω    -41.00 -16.00   0.50    0.20    --  -49.53 115.00 -90.00   50
 42  ω    -81.00 -46.00   0.50    0.20    --  -49.53 115.00 -90.00   70
 43  ω    -77.00 -52.00   0.50    0.75    --  -90.00 115.00 -90.00   50
 44  ω    -49.00 -22.00   0.50    0.75    --  -90.00  45.00-120.00   54
 45  ω   -100.00 -75.00   0.50    0.20    --  -49.53 169.00  53.00   50
 46  ω    -76.00 -51.00   0.50    0.75    --  -90.00 169.00  53.00   50
 47  ω     82.00 116.00   0.50    0.20    --   49.53  57.00-120.00   68
 48  ω    103.00 168.00   0.50    0.75    --  111.50  45.00-180.00  130
 49  ω    109.00 174.00   0.50    0.75    --  111.50  45.00-120.00  130
 50  ω    112.00 137.00   0.50    0.75    --  111.50  30.00-180.00   50
 51  ω    126.00 178.00   0.50    0.75    --  111.50  45.00 -90.00  104
 52  ω    106.00 175.00   0.50    0.75    --  111.50  15.00 -30.00  138
 53  ω    104.00 178.00   0.50    0.75    --  111.50  30.00   0.00  148
 54  ω    102.00 163.00   0.50    0.75    --  111.50  45.00  30.00  122
 55  ω    104.00 176.00   0.50    0.75    --  111.50  15.00  90.00  144
 56  ω    125.00 152.00   0.50    0.75    --  111.50 115.00 -90.00   54
 57  ω     80.00 110.00   0.50    0.75    --  111.50 169.00  53.00   60
 58  ω     67.00 121.00   0.50    0.20    --   49.53 169.00  53.00  108
 59  ω   -100.00 -75.00   0.50    0.80    --  -90.00 169.00  53.00   50
 60  ω     82.00 107.00   0.50    0.80    --  111.50-103.00-115.15   50
 61  ω     33.00  58.00   0.50    0.20    --   49.78-115.00-179.00   50
;
_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      -0.1686496000
_diffrn_orient_matrix_UB_12      -0.0850397000
_diffrn_orient_matrix_UB_13      -0.0654293000
_diffrn_orient_matrix_UB_21      0.0877208000
_diffrn_orient_matrix_UB_22      0.0691195000
_diffrn_orient_matrix_UB_23      -0.0637603000
_diffrn_orient_matrix_UB_31      0.0574981000
_diffrn_orient_matrix_UB_32      -0.1614076000
_diffrn_orient_matrix_UB_33      -0.0152701000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4204
_reflns_number_total             4692
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.
;

# start Validation Reply Form
_vrf_PLAT906_final               
;
PROBLEM: Large K Value in the Analysis of Variance ...... 5.928 Check 
RESPONSE: The K value is large only for weak reflections with Fc/Fcmax 
lower than 0.024.
;
# end Validation Reply Form

_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.059
_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)+(0.0557P)²+0.7740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_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:
 C20(H20), C22(H22), C17(H17), C16(H16), C7(H7), C21(H21), C18(H18), C5(H5),
 C15(H15), C8(H8), C14(H14), C24(H24), C4(H4), C23(H23)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_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
S2 S 0.27627(5) 0.94367(5) 0.17743(2) 0.01607(12) Uani 1 1 d . . . . .
S1 S 0.59463(5) 0.82921(5) 0.15429(2) 0.01772(12) Uani 1 1 d . . . . .
F1 F 0.30150(13) 0.63569(13) 0.16057(6) 0.0183(2) Uani 1 1 d . . . . .
O5 O 0.16849(16) 0.92508(17) 0.23288(8) 0.0211(3) Uani 1 1 d . . . . .
O4 O 0.38922(16) 1.10567(16) 0.17881(8) 0.0221(3) Uani 1 1 d . . . . .
O1 O 0.54241(17) 0.95154(17) 0.32994(8) 0.0251(3) Uani 1 1 d . . . . .
O2 O 0.52305(17) 0.79858(19) 0.06925(8) 0.0253(3) Uani 1 1 d . . . . .
O3 O 0.71564(17) 0.98750(17) 0.19583(9) 0.0244(3) Uani 1 1 d . . . . .
C20 C -0.0021(2) 0.7209(2) 0.06953(11) 0.0180(3) Uani 1 1 d . . . . .
H20 H -0.029607 0.675826 0.114219 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4585(2) 0.8126(2) 0.29151(10) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.4080(2) 0.7949(2) 0.19943(10) 0.0166(3) Uani 1 1 d . . . . .
C22 C -0.0675(2) 0.7241(2) -0.07168(11) 0.0210(4) Uani 1 1 d . . . . .
H22 H -0.141870 0.680061 -0.123948 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6777(2) 0.6627(2) 0.17817(10) 0.0168(3) Uani 1 1 d . . . . .
C17 C 0.8744(2) 0.5628(3) 0.26677(11) 0.0234(4) Uani 1 1 d . . . . .
H17 H 0.963826 0.581268 0.313949 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8107(3) 0.4046(3) 0.21598(12) 0.0241(4) Uani 1 1 d . . . . .
H16 H 0.856008 0.314996 0.229290 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2767(2) 0.5784(2) 0.43795(11) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.246279 0.607684 0.486897 0.024 Uiso 1 1 calc R U . . .
C21 C -0.1089(2) 0.6563(2) -0.00680(11) 0.0205(4) Uani 1 1 d . . . . .
H21 H -0.210644 0.565631 -0.014995 0.025 Uiso 1 1 calc R U . . .
C18 C 0.8072(2) 0.6944(2) 0.24861(10) 0.0189(3) Uani 1 1 d . . . . .
H18 H 0.848381 0.802811 0.283219 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3030(2) 0.3706(2) 0.33493(11) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.291844 0.256126 0.312872 0.025 Uiso 1 1 calc R U . . .
C15 C 0.6813(2) 0.3754(2) 0.14571(12) 0.0227(4) Uani 1 1 d . . . . .
H15 H 0.639587 0.266760 0.111308 0.027 Uiso 1 1 calc R U . . .
C19 C 0.1472(2) 0.8537(2) 0.07966(10) 0.0167(3) Uani 1 1 d . . . . .
C9 C 0.1634(2) 0.2652(2) 0.44365(10) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.3449(2) 0.7061(2) 0.40021(11) 0.0199(4) Uani 1 1 d . . . . .
H8 H 0.361115 0.820986 0.423583 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2469(3) 0.1200(3) 0.43856(12) 0.0264(4) Uani 1 1 d . . . . .
H10A H 0.370539 0.164264 0.464196 0.040 Uiso 1 1 calc R U . . .
H10B H 0.230130 0.068843 0.382017 0.040 Uiso 1 1 calc R U . . .
H10C H 0.193269 0.034107 0.466204 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3898(2) 0.6667(2) 0.32800(10) 0.0180(3) Uani 1 1 d . . . . .
C14 C 0.6141(2) 0.5049(2) 0.12628(11) 0.0196(3) Uani 1 1 d . . . . .
H14 H 0.526210 0.486817 0.078514 0.024 Uiso 1 1 calc R U . . .
C12 C 0.1712(3) 0.3278(3) 0.53202(11) 0.0263(4) Uani 1 1 d . . . . .
H12A H 0.121155 0.231831 0.555056 0.040 Uiso 1 1 calc R U . . .
H12B H 0.105924 0.410745 0.535788 0.040 Uiso 1 1 calc R U . . .
H12C H 0.291582 0.381092 0.561766 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2513(2) 0.4078(2) 0.40606(10) 0.0177(3) Uani 1 1 d . . . . .
C24 C 0.1927(2) 0.9220(2) 0.01545(11) 0.0185(3) Uani 1 1 d . . . . .
H24 H 0.295971 1.010753 0.023382 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3700(2) 0.4969(2) 0.29620(11) 0.0206(4) Uani 1 1 d . . . . .
H4 H 0.402687 0.468154 0.247813 0.025 Uiso 1 1 calc R U . . .
C23 C 0.0822(2) 0.8560(2) -0.06054(11) 0.0205(4) Uani 1 1 d . . . . .
H23 H 0.108983 0.901227 -0.105295 0.025 Uiso 1 1 calc R U . . .
C11 C -0.0272(3) 0.1961(3) 0.39562(13) 0.0288(4) Uani 1 1 d . . . . .
H11A H -0.032910 0.149699 0.339657 0.043 Uiso 1 1 calc R U . . .
H11B H -0.081450 0.288100 0.397302 0.043 Uiso 1 1 calc R U . . .
H11C H -0.087971 0.106640 0.419434 0.043 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
S2 O5 1.4364(13) . ?
S2 O4 1.4295(13) . ?
S2 C1 1.8715(17) . ?
S2 C19 1.7568(18) . ?
S1 O2 1.4333(14) . ?
S1 O3 1.4283(15) . ?
S1 C1 1.8465(17) . ?
S1 C13 1.7561(17) . ?
F1 C1 1.383(2) . ?
O1 C2 1.208(2) . ?
C20 C21 1.382(2) . ?
C20 C19 1.397(2) . ?
C2 C1 1.542(2) . ?
C2 C3 1.487(2) . ?
C22 C21 1.392(3) . ?
C22 C23 1.392(3) . ?
C13 C18 1.395(2) . ?
C13 C14 1.395(3) . ?
C17 C16 1.389(3) . ?
C17 C18 1.392(3) . ?
C16 C15 1.395(3) . ?
C7 C8 1.386(3) . ?
C7 C6 1.397(3) . ?
C5 C6 1.405(2) . ?
C5 C4 1.386(3) . ?
C15 C14 1.383(3) . ?
C19 C24 1.394(2) . ?
C9 C10 1.535(3) . ?
C9 C12 1.531(2) . ?
C9 C6 1.529(2) . ?
C9 C11 1.546(3) . ?
C8 C3 1.396(2) . ?
C3 C4 1.400(3) . ?
C24 C23 1.390(3) . ?

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
O5 S2 C1 103.25(8) . . ?
O5 S2 C19 108.60(8) . . ?
O4 S2 O5 120.41(8) . . ?
O4 S2 C1 108.90(8) . . ?
O4 S2 C19 110.16(8) . . ?
C19 S2 C1 104.14(8) . . ?
O2 S1 C1 105.49(8) . . ?
O2 S1 C13 109.48(8) . . ?
O3 S1 O2 120.83(9) . . ?
O3 S1 C1 108.23(8) . . ?
O3 S1 C13 109.60(8) . . ?
C13 S1 C1 101.36(8) . . ?
C21 C20 C19 118.67(16) . . ?
O1 C2 C1 116.30(15) . . ?
O1 C2 C3 123.95(16) . . ?
C3 C2 C1 119.49(15) . . ?
S1 C1 S2 112.69(9) . . ?
F1 C1 S2 105.35(11) . . ?
F1 C1 S1 105.49(11) . . ?
F1 C1 C2 112.52(13) . . ?
C2 C1 S2 107.19(11) . . ?
C2 C1 S1 113.40(11) . . ?
C21 C22 C23 120.49(17) . . ?
C18 C13 S1 118.31(14) . . ?
C14 C13 S1 119.38(13) . . ?
C14 C13 C18 122.31(16) . . ?
C16 C17 C18 120.07(17) . . ?
C17 C16 C15 120.97(17) . . ?
C8 C7 C6 121.87(17) . . ?
C20 C21 C22 120.07(17) . . ?
C17 C18 C13 118.14(17) . . ?
C4 C5 C6 121.53(17) . . ?
C14 C15 C16 119.81(18) . . ?
C20 C19 S2 118.61(13) . . ?
C24 C19 S2 119.01(14) . . ?
C24 C19 C20 122.32(16) . . ?
C10 C9 C11 108.56(16) . . ?
C12 C9 C10 108.39(15) . . ?
C12 C9 C11 109.19(16) . . ?
C6 C9 C10 111.27(15) . . ?
C6 C9 C12 111.80(15) . . ?
C6 C9 C11 107.56(14) . . ?
C7 C8 C3 120.30(17) . . ?
C8 C3 C2 116.11(16) . . ?
C8 C3 C4 118.73(16) . . ?
C4 C3 C2 125.15(16) . . ?
C15 C14 C13 118.70(17) . . ?
C7 C6 C5 117.15(16) . . ?
C7 C6 C9 122.29(15) . . ?
C5 C6 C9 120.49(16) . . ?
C23 C24 C19 117.84(16) . . ?
C5 C4 C3 120.34(16) . . ?
C24 C23 C22 120.60(16) . . ?

_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 1.928
_oxdiff_exptl_absorpt_empirical_full_min 0.434
####################################################################### 
# 
# 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_prakash1140_auto
_database_code_depnum_ccdc_archive 'CCDC 2427880'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 F O5 S2'
_chemical_formula_sum            'C21 H17 F O5 S2'
_chemical_formula_weight         432.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H25S2O5F
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.6210(4)
_cell_length_b                   8.2842(2)
_cell_length_c                   15.5276(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.877(3)
_cell_angle_gamma                90
_cell_volume                     1923.65(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11526
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2570
_cell_measurement_theta_min      2.9490
_shelx_estimated_absorpt_T_max   0.670
_shelx_estimated_absorpt_T_min   0.482
_exptl_absorpt_coefficient_mu    2.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.151
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21635
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         80.089
_diffrn_reflns_theta_min         2.955
_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 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  72.00   0.50    1.25    --  111.50 -61.00 -60.00   60
  2  ω     46.00  72.00   0.50    1.25    --  111.50 -61.00   0.00   52
  3  ω     43.00  72.00   0.50    1.25    --  111.50 -61.00 120.00   58
  4  ω     43.00 104.00   0.50    0.35    --   49.66-141.00 142.00  122
  5  ω     43.00 123.00   0.50    1.25    --  111.50-141.00 142.00  160
  6  ω     45.00  86.00   0.50    1.25    --  111.50-125.00  90.00   82
  7  ω     44.00  69.00   0.50    1.25    --  111.50 -95.00  30.00   50
  8  ω     70.00 104.00   0.50    1.25    --  111.50 -95.00 -60.00   68
  9  ω     44.00  99.00   0.50    1.25    --  111.50-125.00 -90.00  110
 10  ω     42.00 115.00   0.50    1.25    --  111.50-130.00 -44.00  146
 11  ω     67.00 105.00   0.50    1.25    --  111.50 -95.00 -30.00   76
 12  ω     64.00 104.00   0.50    1.25    --  111.50 -95.00   0.00   80
 13  ω     79.00 105.00   0.50    1.25    --  111.50 -95.00  30.00   52
 14  ω     37.00  97.00   0.50    0.35    --   49.66-130.00 -44.00  120
 15  ω    104.00 178.00   0.50    1.25    --  111.50  15.00  30.00  148
 16  ω    104.00 154.00   0.50    1.25    --  111.50  45.00 120.00  100
 17  ω     82.00 121.00   0.50    0.35    --   49.66  57.00  90.00   78
 18  ω    102.00 170.00   0.50    1.25    --  111.50  77.00 -30.00  136
 19  ω    126.00 153.00   0.50    1.25    --  111.50  30.00-150.00   54
 20  ω     84.00 173.00   0.50    1.25    --  111.50 141.00-159.00  178
 21  ω     96.00 152.00   0.50    1.25    --  111.50 125.00   0.00  112
 22  ω     92.00 178.00   0.50    1.25    --  111.50 130.00  27.00  172
 23  ω    -90.00 -16.00   0.50    0.35    --  -49.66 130.00  27.00  148
 24  ω    -98.00 -21.00   0.50    1.25    --  -90.00 141.00-159.00  154
 25  ω    -50.00 -18.00   0.50    1.25    --  -90.00  45.00-150.00   64
 26  ω   -120.00 -63.00   0.50    0.35    --  -49.66-141.00 142.00  114
 27  ω   -120.00 -82.00   0.50    0.35    --  -49.66 -57.00 150.00   76
 28  ω   -120.00 -82.00   0.50    0.35    --  -49.66 -57.00 120.00   76
 29  ω   -120.00 -82.00   0.50    0.35    --  -49.66 -57.00  30.00   76
 30  ω   -119.00 -70.00   0.50    0.35    --  -49.66-130.00 -44.00   98
 31  ω     50.00  75.00   0.50    0.50    --   49.78-141.00 142.00   50
 32  ω   -119.00 -94.00   0.50    0.50    --  -49.78-130.00 -44.00   50
 33  ω   -119.00 -94.00   0.50    0.50    --  -49.78-130.00 -44.00   50
 34  ω     50.00  75.00   0.50    0.50    --   49.78-141.00 142.00   50
;
_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      0.0136920000
_diffrn_orient_matrix_UB_12      0.1835984000
_diffrn_orient_matrix_UB_13      -0.0020731000
_diffrn_orient_matrix_UB_21      0.0972290000
_diffrn_orient_matrix_UB_22      -0.0282453000
_diffrn_orient_matrix_UB_23      0.0160975000
_diffrn_orient_matrix_UB_31      -0.0313476000
_diffrn_orient_matrix_UB_32      -0.0075248000
_diffrn_orient_matrix_UB_33      -0.1090218000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3555
_reflns_number_total             4082
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.
;
# start Validation Reply Form
_vrf_PLAT906_prakash1140_auto    
;
PROBLEM: Large K Value in the Analysis of Variance ......      4.804 Check 
RESPONSE: The K value is large only for weak reflections with Fc/Fcmax 
lower than 0.029.
;

# end Validation Reply Form


_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.089
_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)+(0.0459P)²+4.3056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1376
_refine_special_details          ?
_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:
 C21(H21), C17(H17), C15(H15), C14(H14), C11(H11), C13(H13), C4(H4), C12(H12),
 C8(H8), C5(H5), C7(H7), C20(H20), C19(H19), C18(H18)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
S2 S 0.32723(4) 0.51183(8) 0.50754(4) 0.02256(17) Uani 1 1 d . . . . .
S1 S 0.28114(5) 0.84938(9) 0.56035(5) 0.02670(18) Uani 1 1 d . . . . .
F1 F 0.30367(10) 0.7729(2) 0.40900(11) 0.0253(4) Uani 1 1 d . . . . .
O5 O 0.29166(15) 0.4271(3) 0.56303(14) 0.0312(5) Uani 1 1 d . . . . .
O4 O 0.41967(14) 0.5577(3) 0.54851(15) 0.0313(5) Uani 1 1 d . . . . .
O1 O 0.13001(14) 0.6151(3) 0.45512(14) 0.0324(5) Uani 1 1 d . . . . .
O3 O 0.28385(15) 0.7615(3) 0.64060(15) 0.0354(5) Uani 1 1 d . . . . .
O2 O 0.21362(15) 0.9681(3) 0.51231(17) 0.0406(6) Uani 1 1 d . . . . .
C10 C 0.38618(19) 0.9392(3) 0.5903(2) 0.0243(6) Uani 1 1 d . . . . .
C16 C 0.29819(18) 0.4106(3) 0.39834(19) 0.0218(5) Uani 1 1 d . . . . .
C21 C 0.21981(19) 0.3195(4) 0.3613(2) 0.0266(6) Uani 1 1 d . . . . .
H21 H 0.184164 0.309736 0.394965 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3522(2) 0.4264(4) 0.3515(2) 0.0265(6) Uani 1 1 d . . . . .
H17 H 0.405206 0.489431 0.377961 0.032 Uiso 1 1 calc R U . . .
C15 C 0.45753(19) 0.8925(4) 0.6750(2) 0.0265(6) Uani 1 1 d . . . . .
H15 H 0.451801 0.805569 0.711853 0.032 Uiso 1 1 calc R U . . .
C3 C 0.11550(18) 0.6922(4) 0.3012(2) 0.0253(6) Uani 1 1 d . . . . .
C1 C 0.26500(19) 0.7030(4) 0.46305(19) 0.0239(6) Uani 1 1 d . . . . .
C14 C 0.5377(2) 0.9763(4) 0.7045(2) 0.0290(6) Uani 1 1 d . . . . .
H14 H 0.587068 0.948582 0.763120 0.035 Uiso 1 1 calc R U . . .
C2 C 0.16400(19) 0.6696(4) 0.4065(2) 0.0251(6) Uani 1 1 d . . . . .
C11 C 0.3939(2) 1.0623(4) 0.5341(2) 0.0310(7) Uani 1 1 d . . . . .
H11 H 0.344324 1.091538 0.475960 0.037 Uiso 1 1 calc R U . . .
C13 C 0.5459(2) 1.0995(4) 0.6490(2) 0.0296(6) Uani 1 1 d . . . . .
H13 H 0.601085 1.155681 0.669800 0.036 Uiso 1 1 calc R U . . .
C6 C 0.01184(19) 0.7174(4) 0.1030(2) 0.0265(6) Uani 1 1 d . . . . .
C4 C 0.0383(2) 0.6007(4) 0.2555(2) 0.0328(7) Uani 1 1 d . . . . .
H4 H 0.020272 0.529375 0.291737 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4749(2) 1.1423(4) 0.5635(2) 0.0329(7) Uani 1 1 d . . . . .
H12 H 0.481482 1.225983 0.525303 0.039 Uiso 1 1 calc R U . . .
C8 C 0.1408(2) 0.7968(4) 0.2471(2) 0.0307(7) Uani 1 1 d . . . . .
H8 H 0.193720 0.859385 0.277384 0.037 Uiso 1 1 calc R U . . .
C5 C -0.0121(2) 0.6128(4) 0.1582(2) 0.0336(7) Uani 1 1 d . . . . .
H5 H -0.064394 0.548499 0.127966 0.040 Uiso 1 1 calc R U . . .
C7 C 0.0885(2) 0.8100(4) 0.1485(2) 0.0314(7) Uani 1 1 d . . . . .
H7 H 0.105558 0.882939 0.112186 0.038 Uiso 1 1 calc R U . . .
C20 C 0.1954(2) 0.2439(4) 0.2741(2) 0.0338(7) Uani 1 1 d . . . . .
H20 H 0.141866 0.182289 0.246884 0.041 Uiso 1 1 calc R U . . .
C19 C 0.2484(2) 0.2573(4) 0.2260(2) 0.0366(8) Uani 1 1 d . . . . .
H19 H 0.231347 0.204482 0.166305 0.044 Uiso 1 1 calc R U . . .
C18 C 0.3264(2) 0.3477(4) 0.2649(2) 0.0337(7) Uani 1 1 d . . . . .
H18 H 0.362570 0.355619 0.231711 0.040 Uiso 1 1 calc R U . . .
C9 C -0.0453(2) 0.7307(5) -0.0035(2) 0.0411(8) Uani 1 1 d . . . . .
H9A H -0.080833 0.632055 -0.026812 0.062 Uiso 1 1 calc R U . . .
H9B H -0.006822 0.744860 -0.036049 0.062 Uiso 1 1 calc R U . . .
H9C H -0.085404 0.823725 -0.016865 0.062 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
S2 O5 1.424(2) . ?
S2 O4 1.434(2) . ?
S2 C16 1.760(3) . ?
S2 C1 1.853(3) . ?
S1 O3 1.427(2) . ?
S1 O2 1.433(2) . ?
S1 C10 1.763(3) . ?
S1 C1 1.863(3) . ?
F1 C1 1.387(3) . ?
O1 C2 1.210(4) . ?
C10 C15 1.387(4) . ?
C10 C11 1.385(4) . ?
C16 C21 1.394(4) . ?
C16 C17 1.386(4) . ?
C21 C20 1.382(4) . ?
C17 C18 1.383(4) . ?
C15 C14 1.391(4) . ?
C3 C2 1.486(4) . ?
C3 C4 1.389(4) . ?
C3 C8 1.394(4) . ?
C1 C2 1.542(4) . ?
C14 C13 1.380(5) . ?
C11 C12 1.386(5) . ?
C13 C12 1.384(5) . ?
C6 C5 1.394(4) . ?
C6 C7 1.387(4) . ?
C6 C9 1.510(4) . ?
C4 C5 1.375(4) . ?
C8 C7 1.397(4) . ?
C20 C19 1.386(5) . ?
C19 C18 1.386(5) . ?

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
O5 S2 O4 120.63(13) . . ?
O5 S2 C16 109.66(14) . . ?
O5 S2 C1 109.58(14) . . ?
O4 S2 C16 110.11(13) . . ?
O4 S2 C1 104.74(13) . . ?
C16 S2 C1 100.04(13) . . ?
O3 S1 O2 121.60(16) . . ?
O3 S1 C10 109.54(13) . . ?
O3 S1 C1 108.35(14) . . ?
O2 S1 C10 107.94(15) . . ?
O2 S1 C1 102.82(13) . . ?
C10 S1 C1 105.33(13) . . ?
C15 C10 S1 118.1(2) . . ?
C11 C10 S1 119.9(2) . . ?
C11 C10 C15 121.8(3) . . ?
C21 C16 S2 118.0(2) . . ?
C17 C16 S2 119.5(2) . . ?
C17 C16 C21 122.4(3) . . ?
C20 C21 C16 118.2(3) . . ?
C18 C17 C16 117.9(3) . . ?
C10 C15 C14 118.2(3) . . ?
C4 C3 C2 115.5(3) . . ?
C4 C3 C8 119.1(3) . . ?
C8 C3 C2 125.5(3) . . ?
S2 C1 S1 113.24(14) . . ?
F1 C1 S2 104.59(18) . . ?
F1 C1 S1 106.16(19) . . ?
F1 C1 C2 114.1(2) . . ?
C2 C1 S2 110.5(2) . . ?
C2 C1 S1 108.30(19) . . ?
C13 C14 C15 120.3(3) . . ?
O1 C2 C3 123.8(3) . . ?
O1 C2 C1 113.6(2) . . ?
C3 C2 C1 122.4(2) . . ?
C10 C11 C12 119.2(3) . . ?
C14 C13 C12 120.8(3) . . ?
C5 C6 C9 120.4(3) . . ?
C7 C6 C5 118.5(3) . . ?
C7 C6 C9 121.1(3) . . ?
C5 C4 C3 120.4(3) . . ?
C13 C12 C11 119.6(3) . . ?
C3 C8 C7 120.2(3) . . ?
C4 C5 C6 121.3(3) . . ?
C6 C7 C8 120.6(3) . . ?
C21 C20 C19 120.5(3) . . ?
C18 C19 C20 120.2(3) . . ?
C17 C18 C19 120.8(3) . . ?

_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 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.628
####################################################################### 
# 
# 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_final_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2427871'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 F O6 S2'
_chemical_formula_sum            'C18 H13 F O6 S2'
_chemical_formula_weight         408.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O6F
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.5720(4)
_cell_length_b                   6.25740(10)
_cell_length_c                   16.8517(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.768(3)
_cell_angle_gamma                90
_cell_volume                     1748.51(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4600
_cell_measurement_theta_min      2.6430
_shelx_estimated_absorpt_T_max   0.672
_shelx_estimated_absorpt_T_min   0.470
_exptl_absorpt_coefficient_mu    3.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0810
-1 2 0 0.1288
1 0 2 0.0832
-1 0 -2 0.0533
1 0 0 0.0932
-1 0 0 0.0672
-1 -1 1 0.0632
1 1 -1 0.1237
1 0 -1 0.0937
-1 0 1 0.1020

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.136
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
0.0015 -0.0003 0.9988 0.0316 0.0798 -0.0557
-0.9925 1.9993 0.0007 0.0639 0.2284 0.4411
1.0033 -0.0010 1.9959 -0.0029 0.2131 -0.1490
-1.0033 0.0010 -1.9959 0.0029 -0.2131 0.1490
1.0003 -0.0005 -0.0017 -0.0660 0.0534 -0.0376
-1.0003 0.0005 0.0017 0.0660 -0.0534 0.0376
-1.0026 -0.9992 1.0010 0.0986 -0.1146 -0.2197
1.0026 0.9992 -1.0010 -0.0986 0.1146 0.2197
0.9987 -0.0002 -1.0005 -0.0976 -0.0264 0.0180
-0.9987 0.0002 1.0005 0.0976 0.0264 -0.0180

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14237
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.795
_diffrn_reflns_theta_min         2.665
_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 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -23.60   0.60    0.80    --  -90.00  45.00 150.00   44
  2  ω    -51.00   9.00   0.60    0.40    --  -49.53  46.00 -14.00  100
  3  ω    -49.00 -19.00   0.60    0.80    --  -90.00  46.00 -14.00   50
  4  ω    -50.00 -20.00   0.60    0.80    --  -90.00  45.00-180.00   50
  5  ω   -121.00 -40.00   0.60    0.40    --  -49.53 -46.00-164.00  135
  6  ω   -114.00 -87.00   0.60    0.40    --  -49.53 -57.00-180.00   45
  7  ω   -157.00-130.00   0.60    0.80    --  -90.00 -46.00-164.00   45
  8  ω   -118.00 -88.00   0.60    0.40    --  -49.53-125.00   0.00   50
  9  ω   -117.00 -88.20   0.60    0.40    --  -49.53-125.00 150.00   48
 10  ω    -15.00  39.00   0.60    0.40    --   49.53 -46.00-164.00   90
 11  ω     44.00  71.00   0.60    0.80    --  111.50 -61.00-150.00   45
 12  ω     43.00  92.80   0.60    0.80    --  111.50 -77.00 -90.00   83
 13  ω     43.00  71.80   0.60    0.80    --  111.50 -61.00-180.00   48
 14  ω     41.00  66.80   0.60    0.80    --  111.50 -61.00 -60.00   43
 15  ω     41.00  65.60   0.60    0.80    --  111.50 -61.00 -30.00   41
 16  ω     43.00  82.00   0.60    0.80    --  111.50 -77.00   0.00   65
 17  ω     41.00  71.00   0.60    0.80    --  111.50 -61.00  60.00   50
 18  ω     43.00  70.60   0.60    0.80    --  111.50 -61.00  90.00   46
 19  ω     42.00  72.00   0.60    0.80    --  111.50 -61.00 120.00   50
 20  ω     41.00  68.60   0.60    0.80    --  111.50 -61.00 150.00   46
 21  ω    113.00 157.40   0.60    0.80    --  111.50 125.00 150.00   74
 22  ω     44.00 101.60   0.60    0.80    --  111.50 -95.00 -30.00   96
 23  ω     41.00  68.60   0.60    0.80    --  111.50 -95.00 -60.00   46
 24  ω     42.00  96.00   0.60    0.80    --  111.50 -95.00-120.00   90
 25  ω     49.00 100.00   0.60    0.80    --  111.50 -95.00 120.00   85
 26  ω    110.00 176.60   0.60    0.80    --  111.50  45.00  60.00  111
 27  ω    149.00 176.60   0.60    0.80    --  111.50  45.00  90.00   46
 28  ω    117.00 146.40   0.60    0.80    --  111.50  45.00  90.00   49
 29  ω    108.00 177.00   0.60    0.80    --  111.50  46.00 -14.00  115
 30  ω     87.00 117.00   0.60    0.40    --   49.53  57.00 -90.00   50
 31  ω     56.00  81.80   0.60    0.40    --   49.53  46.00 -14.00   43
;
_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      -0.0659165000
_diffrn_orient_matrix_UB_12      -0.0007873000
_diffrn_orient_matrix_UB_13      0.0317011000
_diffrn_orient_matrix_UB_21      0.0536394000
_diffrn_orient_matrix_UB_22      0.1408454000
_diffrn_orient_matrix_UB_23      0.0798750000
_diffrn_orient_matrix_UB_31      -0.0376220000
_diffrn_orient_matrix_UB_32      0.2019501000
_diffrn_orient_matrix_UB_33      -0.0556202000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3271
_reflns_number_total             3712
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.047
_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)+(0.0472P)²+1.2257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_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
C1 C 0.24315(10) 0.6107(3) 0.74870(11) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.27030(10) 0.6480(3) 0.67587(11) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.26574(10) 0.4734(3) 0.61813(11) 0.0189(3) Uani 1 1 d . . . . .
C4 C 0.23732(11) 0.2681(3) 0.60525(12) 0.0206(4) Uani 1 1 d . . . . .
H4 H 0.214527 0.195255 0.638018 0.025 Uiso 1 1 calc R U . . .
C5 C 0.24864(11) 0.1858(3) 0.53335(12) 0.0223(4) Uani 1 1 d . . . . .
H5 H 0.234932 0.046826 0.508257 0.027 Uiso 1 1 calc R U . . .
C6 C 0.28284(11) 0.3444(3) 0.50762(12) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.297117 0.332542 0.460293 0.027 Uiso 1 1 calc R U . . .
C7 C 0.41069(10) 0.5996(3) 0.86216(11) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.43282(11) 0.3930(3) 0.89342(12) 0.0236(4) Uani 1 1 d . . . . .
H8 H 0.399487 0.308058 0.910168 0.028 Uiso 1 1 calc R U . . .
C9 C 0.50518(12) 0.3131(3) 0.89961(13) 0.0285(4) Uani 1 1 d . . . . .
H9 H 0.521697 0.172059 0.920888 0.034 Uiso 1 1 calc R U . . .
C10 C 0.55319(11) 0.4387(4) 0.87483(12) 0.0294(4) Uani 1 1 d . . . . .
H10 H 0.602817 0.383633 0.880064 0.035 Uiso 1 1 calc R U . . .
C11 C 0.52949(11) 0.6435(4) 0.84252(13) 0.0288(4) Uani 1 1 d . . . . .
H11 H 0.562530 0.727393 0.824986 0.035 Uiso 1 1 calc R U . . .
C12 C 0.45746(11) 0.7270(3) 0.83566(12) 0.0243(4) Uani 1 1 d . . . . .
H12 H 0.440631 0.867245 0.813468 0.029 Uiso 1 1 calc R U . . .
C13 C 0.11530(10) 0.6940(3) 0.79668(12) 0.0200(3) Uani 1 1 d . . . . .
C14 C 0.12387(11) 0.8605(3) 0.85491(12) 0.0249(4) Uani 1 1 d . . . . .
H14 H 0.146248 0.993448 0.850067 0.030 Uiso 1 1 calc R U . . .
C15 C 0.09894(12) 0.8279(4) 0.92038(13) 0.0312(4) Uani 1 1 d . . . . .
H15 H 0.103681 0.939792 0.960561 0.037 Uiso 1 1 calc R U . . .
C16 C 0.06722(12) 0.6324(4) 0.92694(13) 0.0334(5) Uani 1 1 d . . . . .
H16 H 0.050417 0.610771 0.971896 0.040 Uiso 1 1 calc R U . . .
C17 C 0.05964(11) 0.4669(4) 0.86844(13) 0.0300(4) Uani 1 1 d . . . . .
H17 H 0.038115 0.333221 0.874062 0.036 Uiso 1 1 calc R U . . .
C18 C 0.08333(10) 0.4961(3) 0.80196(12) 0.0237(4) Uani 1 1 d . . . . .
H18 H 0.077921 0.384696 0.761340 0.028 Uiso 1 1 calc R U . . .
O1 O 0.29440(7) 0.8266(2) 0.67131(8) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.29428(8) 0.5227(2) 0.55773(8) 0.0219(3) Uani 1 1 d . . . . .
O3 O 0.30317(8) 0.5988(2) 0.92182(8) 0.0261(3) Uani 1 1 d . . . . .
O4 O 0.32405(8) 0.9341(2) 0.85627(9) 0.0261(3) Uani 1 1 d . . . . .
O5 O 0.09200(8) 0.6161(2) 0.63445(8) 0.0287(3) Uani 1 1 d . . . . .
O6 O 0.15213(8) 0.9640(2) 0.70296(10) 0.0303(3) Uani 1 1 d . . . . .
F1 F 0.23195(6) 0.39934(16) 0.76125(7) 0.0210(2) Uani 1 1 d . . . . .
S1 S 0.32132(2) 0.70628(7) 0.85804(3) 0.01891(12) Uani 1 1 d . . . . .
S2 S 0.14283(2) 0.73979(7) 0.71104(3) 0.02042(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.540(2) . ?
C1 F1 1.3703(19) . ?
C1 S1 1.8575(17) . ?
C1 S2 1.8604(17) . ?
C2 C3 1.440(2) . ?
C2 O1 1.219(2) . ?
C3 C4 1.369(2) . ?
C3 O2 1.378(2) . ?
C4 C5 1.417(2) . ?
C5 C6 1.351(3) . ?
C6 O2 1.357(2) . ?
C7 C8 1.387(3) . ?
C7 C12 1.392(3) . ?
C7 S1 1.7610(17) . ?
C8 C9 1.393(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.392(3) . ?
C13 C14 1.390(3) . ?
C13 C18 1.393(3) . ?
C13 S2 1.7580(18) . ?
C14 C15 1.390(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.388(3) . ?
O3 S1 1.4308(13) . ?
O4 S1 1.4274(14) . ?
O5 S2 1.4348(14) . ?
O6 S2 1.4277(14) . ?

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
C2 C1 S1 110.59(11) . . ?
C2 C1 S2 107.43(11) . . ?
F1 C1 C2 113.32(14) . . ?
F1 C1 S1 105.24(11) . . ?
F1 C1 S2 105.86(11) . . ?
S1 C1 S2 114.45(9) . . ?
C3 C2 C1 118.90(15) . . ?
O1 C2 C1 116.75(15) . . ?
O1 C2 C3 124.36(16) . . ?
C4 C3 C2 136.09(16) . . ?
C4 C3 O2 110.00(15) . . ?
O2 C3 C2 113.87(15) . . ?
C3 C4 C5 106.37(16) . . ?
C6 C5 C4 106.24(16) . . ?
C5 C6 O2 111.65(15) . . ?
C8 C7 C12 122.32(17) . . ?
C8 C7 S1 118.75(14) . . ?
C12 C7 S1 118.92(14) . . ?
C7 C8 C9 118.28(18) . . ?
C10 C9 C8 120.25(19) . . ?
C11 C10 C9 120.62(17) . . ?
C10 C11 C12 120.23(18) . . ?
C11 C12 C7 118.28(18) . . ?
C14 C13 C18 122.52(17) . . ?
C14 C13 S2 118.29(14) . . ?
C18 C13 S2 119.16(14) . . ?
C13 C14 C15 118.50(19) . . ?
C16 C15 C14 119.91(19) . . ?
C15 C16 C17 120.79(18) . . ?
C18 C17 C16 120.39(19) . . ?
C17 C18 C13 117.88(18) . . ?
C6 O2 C3 105.74(14) . . ?
C7 S1 C1 102.64(8) . . ?
O3 S1 C1 104.51(8) . . ?
O3 S1 C7 109.22(8) . . ?
O4 S1 C1 108.66(8) . . ?
O4 S1 C7 109.73(9) . . ?
O4 S1 O3 120.50(8) . . ?
C13 S2 C1 105.42(8) . . ?
O5 S2 C1 102.99(8) . . ?
O5 S2 C13 109.49(8) . . ?
O6 S2 C1 108.27(8) . . ?
O6 S2 C13 109.34(9) . . ?
O6 S2 O5 120.21(9) . . ?

_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 2.347
_oxdiff_exptl_absorpt_empirical_full_min 0.574
####################################################################### 
# 
# 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_final_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2427876'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 F4 O5 S2'
_chemical_formula_sum            'C21 H14 F4 O5 S2'
_chemical_formula_weight         486.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H23F4S2O5
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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.8594(4)
_cell_length_b                   13.8837(3)
_cell_length_c                   21.9529(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3919.38(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10302
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3520
_cell_measurement_theta_min      4.0090
_shelx_estimated_absorpt_T_max   0.832
_shelx_estimated_absorpt_T_min   0.501
_exptl_absorpt_coefficient_mu    3.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 1 0.1050
0 2 -1 0.1537
1 0 -1 0.0111
-1 0 1 0.0495
-1 1 -2 0.1083
1 -1 2 0.0859
-1 -1 -2 0.0505
1 1 2 0.0688

_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.061
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
-0.0007 -1.9987 0.9983 -0.0046 0.0725 0.2212
0.0007 1.9987 -0.9983 0.0046 -0.0725 -0.2212
0.9952 -0.0051 -0.9964 0.1302 0.0352 -0.0308
-0.9952 0.0051 0.9964 -0.1302 -0.0352 0.0308
-1.0025 0.9960 -1.9935 -0.0044 -0.1944 -0.0918
1.0025 -0.9960 1.9935 0.0044 0.1944 0.0918
-1.0062 -1.0060 -1.9915 0.0404 -0.1711 0.1246
1.0062 1.0060 1.9915 -0.0404 0.1711 -0.1246

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17138
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         82.388
_diffrn_reflns_theta_min         4.027
_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 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -47.00   0.50    1.00    --  -90.00 126.00  -6.00   66
  2  ω    -24.00  10.00   0.50    0.25    --  -49.78  17.00 -67.00   68
  3  ω    -33.00  20.00   0.50    0.25    --  -49.78  38.00  60.00  106
  4  ω   -110.00 -55.00   0.50    0.25    --  -49.78 -17.00 123.00  110
  5  ω   -120.00 -83.00   0.50    0.25    --  -49.78-126.00 -83.00   74
  6  ω     43.00  71.00   0.50    1.00    --  111.50 -61.00  30.00   56
  7  ω     45.00  70.00   0.50    1.00    --  111.50 -61.00 120.00   50
  8  ω     41.00  72.00   0.50    1.00    --  111.50 -61.00 150.00   62
  9  ω     53.00  80.00   0.50    1.00    --  111.50-125.00  60.00   54
 10  ω     83.00 111.00   0.50    1.00    --  111.50-125.00  60.00   56
 11  ω     80.00 105.00   0.50    1.00    --  111.50 -95.00  30.00   50
 12  ω     63.00 105.00   0.50    1.00    --  111.50 -95.00 -60.00   84
 13  ω    110.00 177.00   0.50    1.00    --  111.50  15.00  30.00  134
 14  ω    120.00 174.00   0.50    1.00    --  111.50 110.00  93.00  108
 15  ω    104.00 174.00   0.50    1.00    --  111.50  17.00 -67.00  140
 16  ω    150.00 176.00   0.50    1.00    --  111.50  77.00-180.00   52
 17  ω    115.00 141.00   0.50    1.00    --  111.50  77.00-180.00   52
;
_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      0.0808923000
_diffrn_orient_matrix_UB_12      -0.0225825000
_diffrn_orient_matrix_UB_13      -0.0497310000
_diffrn_orient_matrix_UB_21      0.0844959000
_diffrn_orient_matrix_UB_22      -0.0117347000
_diffrn_orient_matrix_UB_23      0.0491578000
_diffrn_orient_matrix_UB_31      -0.0262276000
_diffrn_orient_matrix_UB_32      -0.1080155000
_diffrn_orient_matrix_UB_33      0.0052543000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3662
_reflns_number_total             4191
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.00060(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.091
_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)+(0.0627P)²+3.9292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_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
C1 C 0.72211(16) 0.58886(14) 0.37229(10) 0.0160(4) Uani 1 1 d . . . . .
S2 S 0.74535(4) 0.56165(3) 0.45483(2) 0.01669(15) Uani 1 1 d . . . . .
F2 F 0.34879(11) 0.58042(10) 0.35799(7) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.72262(12) 0.40634(11) 0.33298(8) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.60541(16) 0.59678(14) 0.35697(10) 0.0168(4) Uani 1 1 d . . . . .
F3 F 0.29938(11) 0.72685(11) 0.37013(7) 0.0347(4) Uani 1 1 d . . . . .
O3 O 0.71547(13) 0.46395(11) 0.46589(8) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.56524(16) 0.67592(14) 0.31722(10) 0.0172(4) Uani 1 1 d . . . . .
F4 F 0.42470(11) 0.67138(10) 0.42403(6) 0.0257(3) Uani 1 1 d . . . . .
O4 O 0.85077(12) 0.59185(12) 0.46431(7) 0.0235(3) Uani 1 1 d . . . . .
C4 C 0.62901(16) 0.71661(15) 0.27267(10) 0.0186(4) Uani 1 1 d . . . . .
H4 H 0.700282 0.698821 0.270860 0.022 Uiso 1 1 calc R U . . .
O5 O 0.55119(12) 0.53352(11) 0.37725(8) 0.0242(4) Uani 1 1 d . . . . .
C5 C 0.59003(17) 0.78286(15) 0.23080(10) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.634398 0.809060 0.200428 0.025 Uiso 1 1 calc R U . . .
C6 C 0.48690(18) 0.81046(15) 0.23343(11) 0.0222(5) Uani 1 1 d . . . . .
H6 H 0.460066 0.855504 0.204900 0.027 Uiso 1 1 calc R U . . .
C7 C 0.42259(17) 0.77177(15) 0.27820(10) 0.0212(4) Uani 1 1 d . . . . .
H7 H 0.351940 0.791522 0.280202 0.025 Uiso 1 1 calc R U . . .
C8 C 0.45943(16) 0.70505(15) 0.31992(10) 0.0183(4) Uani 1 1 d . . . . .
C9 C 0.38400(17) 0.66974(16) 0.36795(11) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.90866(16) 0.48097(14) 0.34536(10) 0.0175(4) Uani 1 1 d . . . . .
C11 C 0.98404(17) 0.54112(15) 0.32004(10) 0.0198(4) Uani 1 1 d . . . . .
H11 H 0.966194 0.587375 0.289909 0.024 Uiso 1 1 calc R U . . .
C12 C 1.08571(17) 0.53148(15) 0.34010(10) 0.0212(4) Uani 1 1 d . . . . .
H12 H 1.138829 0.570651 0.323047 0.025 Uiso 1 1 calc R U . . .
C13 C 1.11024(17) 0.46484(16) 0.38498(10) 0.0217(4) Uani 1 1 d . . . . .
H13 H 1.179943 0.459444 0.398902 0.026 Uiso 1 1 calc R U . . .
C14 C 1.03384(17) 0.40601(15) 0.40970(10) 0.0198(4) Uani 1 1 d . . . . .
H14 H 1.051420 0.360875 0.440553 0.024 Uiso 1 1 calc R U . . .
C15 C 0.93197(17) 0.41292(14) 0.38953(10) 0.0185(4) Uani 1 1 d . . . . .
H15 H 0.879430 0.372052 0.405563 0.022 Uiso 1 1 calc R U . . .
C16 C 0.66267(16) 0.64000(14) 0.49455(9) 0.0170(4) Uani 1 1 d . . . . .
C17 C 0.57996(17) 0.60175(15) 0.52724(10) 0.0193(4) Uani 1 1 d . . . . .
H17 H 0.566692 0.534439 0.526891 0.023 Uiso 1 1 calc R U . . .
C18 C 0.51714(17) 0.66364(16) 0.56039(10) 0.0216(4) Uani 1 1 d . . . . .
H18 H 0.460009 0.638828 0.582901 0.026 Uiso 1 1 calc R U . . .
C19 C 0.53755(17) 0.76185(16) 0.56076(10) 0.0219(4) Uani 1 1 d . . . . .
H19 H 0.493853 0.804042 0.583249 0.026 Uiso 1 1 calc R U . . .
C20 C 0.62199(19) 0.79907(15) 0.52825(10) 0.0218(4) Uani 1 1 d . . . . .
H20 H 0.635572 0.866322 0.529002 0.026 Uiso 1 1 calc R U . . .
C21 C 0.68588(17) 0.73853(15) 0.49498(10) 0.0195(4) Uani 1 1 d . . . . .
H21 H 0.743800 0.763104 0.473071 0.023 Uiso 1 1 calc R U . . .
S1 S 0.77914(4) 0.49318(4) 0.32177(2) 0.01829(15) Uani 1 1 d . . . . .
F1 F 0.77733(9) 0.67152(8) 0.36116(6) 0.0194(3) Uani 1 1 d . . . . .
O1 O 0.77682(13) 0.53706(13) 0.26299(7) 0.0270(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 S2 1.875(2) . ?
C1 C2 1.542(3) . ?
C1 S1 1.879(2) . ?
C1 F1 1.372(2) . ?
S2 O3 1.4305(16) . ?
S2 O4 1.4342(16) . ?
S2 C16 1.753(2) . ?
F2 C9 1.338(3) . ?
O2 S1 1.4291(17) . ?
C2 C3 1.495(3) . ?
C2 O5 1.207(3) . ?
F3 C9 1.347(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.421(3) . ?
F4 C9 1.338(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.514(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.386(3) . ?
C10 S1 1.753(2) . ?
C11 C12 1.386(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.386(3) . ?
C16 C17 1.389(3) . ?
C16 C21 1.400(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.398(3) . ?
C20 C21 1.384(3) . ?
S1 O1 1.4272(18) . ?

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
S2 C1 S1 111.45(10) . . ?
C2 C1 S2 112.35(14) . . ?
C2 C1 S1 107.54(14) . . ?
F1 C1 S2 104.97(13) . . ?
F1 C1 C2 113.91(16) . . ?
F1 C1 S1 106.52(13) . . ?
O3 S2 C1 108.20(9) . . ?
O3 S2 O4 120.43(10) . . ?
O3 S2 C16 109.94(10) . . ?
O4 S2 C1 103.41(9) . . ?
O4 S2 C16 108.64(10) . . ?
C16 S2 C1 105.01(9) . . ?
C3 C2 C1 121.06(17) . . ?
O5 C2 C1 115.47(18) . . ?
O5 C2 C3 123.41(19) . . ?
C4 C3 C2 120.23(18) . . ?
C4 C3 C8 118.47(19) . . ?
C8 C3 C2 121.04(19) . . ?
C5 C4 C3 121.19(19) . . ?
C6 C5 C4 120.1(2) . . ?
C5 C6 C7 119.5(2) . . ?
C8 C7 C6 121.4(2) . . ?
C3 C8 C9 123.39(19) . . ?
C7 C8 C3 119.3(2) . . ?
C7 C8 C9 117.23(19) . . ?
F2 C9 F3 106.14(18) . . ?
F2 C9 C8 113.76(18) . . ?
F3 C9 C8 110.58(18) . . ?
F4 C9 F2 107.37(18) . . ?
F4 C9 F3 105.86(18) . . ?
F4 C9 C8 112.62(18) . . ?
C11 C10 S1 118.99(16) . . ?
C15 C10 C11 122.4(2) . . ?
C15 C10 S1 118.56(16) . . ?
C12 C11 C10 118.1(2) . . ?
C11 C12 C13 120.3(2) . . ?
C12 C13 C14 120.6(2) . . ?
C15 C14 C13 120.2(2) . . ?
C14 C15 C10 118.4(2) . . ?
C17 C16 S2 118.96(16) . . ?
C17 C16 C21 122.24(19) . . ?
C21 C16 S2 118.70(16) . . ?
C18 C17 C16 118.73(19) . . ?
C17 C18 C19 120.1(2) . . ?
C18 C19 C20 120.4(2) . . ?
C21 C20 C19 120.39(19) . . ?
C20 C21 C16 118.1(2) . . ?
O2 S1 C1 107.23(9) . . ?
O2 S1 C10 110.54(10) . . ?
C10 S1 C1 105.35(9) . . ?
O1 S1 C1 102.92(10) . . ?
O1 S1 O2 120.35(11) . . ?
O1 S1 C10 109.16(10) . . ?

_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 5.245
_oxdiff_exptl_absorpt_empirical_full_min 0.515
####################################################################### 
# 
# 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_final_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2427879'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F2 O5 S2'
_chemical_formula_sum            'C20 H14 F2 O5 S2'
_chemical_formula_weight         436.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O5F2
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.33720(10)
_cell_length_b                   16.7082(2)
_cell_length_c                   11.9072(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.452(2)
_cell_angle_gamma                90
_cell_volume                     1900.68(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13522
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.4150
_cell_measurement_theta_min      4.7900
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.585
_exptl_absorpt_coefficient_mu    3.002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 2 0.0666
2 -1 -2 0.0242
0 1 0 0.0623
0 1 -1 0.0374
-2 -1 1 0.0326
-1 0 1 0.0190
2 1 -2 0.0241

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
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
1.0051 -0.9985 1.9949 -0.2265 0.2352 0.2017
1.9960 -1.0005 -1.9998 -0.2791 -0.1317 -0.1624
0.0004 0.9999 -0.0002 0.0251 -0.0643 0.0611
-0.0020 0.9993 -0.9984 0.0499 -0.1539 -0.0434
-1.9992 -0.9998 1.0019 0.2536 0.1705 -0.0644
-0.9982 0.0003 1.0000 0.1270 0.0980 0.0506
1.9968 0.9992 -2.0001 -0.2289 -0.2602 -0.0401

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21344
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.963
_diffrn_reflns_theta_min         4.812
_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 0.976
_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 -87.00   0.50    0.05    --  -49.53-125.00-180.00   62
  2  ω   -118.00 -87.00   0.50    0.05    --  -49.53-125.00-150.00   62
  3  ω   -118.00 -87.00   0.50    0.05    --  -49.53-125.00-120.00   62
  4  ω   -161.00 -74.00   0.50    0.30    --  -90.00 -65.00  43.00  174
  5  ω   -121.00 -34.00   0.50    0.05    --  -49.53 -65.00  43.00  174
  6  ω     41.00  84.00   0.50    0.30    --  111.50 -77.00 -30.00   86
  7  ω     73.00 105.00   0.50    0.30    --  111.50 -77.00 -30.00   64
  8  ω     41.00  72.00   0.50    0.30    --  111.50 -61.00   0.00   62
  9  ω     41.00  79.00   0.50    0.30    --  111.50 -65.00  43.00   76
 10  ω     42.00  78.00   0.50    0.30    --  111.50 -77.00 120.00   72
 11  ω     42.00  71.00   0.50    0.30    --  111.50 -61.00 120.00   58
 12  ω    -21.00  65.00   0.50    0.05    --   49.53 -65.00  43.00  172
 13  ω     41.00  66.00   0.50    0.30    --  111.50 -61.00  90.00   50
 14  ω     41.00  72.00   0.50    0.30    --  111.50 -61.00 -30.00   62
 15  ω     41.00  72.00   0.50    0.30    --  111.50 -61.00 -90.00   62
 16  ω     41.00  72.00   0.50    0.30    --  111.50 -61.00-120.00   62
 17  ω     41.00  72.00   0.50    0.30    --  111.50 -61.00-180.00   62
 18  ω     53.00  97.00   0.50    0.30    --  111.50 -95.00-120.00   88
 19  ω     70.00 100.00   0.50    0.30    --  111.50 -95.00 -30.00   60
 20  ω     42.00  69.00   0.50    0.30    --  111.50 -95.00 120.00   54
 21  ω    104.00 177.00   0.50    0.30    --  111.50  30.00 120.00  146
 22  ω     96.00 178.00   0.50    0.30    --  111.50  65.00 179.00  164
 23  ω     96.00 178.00   0.50    0.30    --  111.50  65.00 179.00  164
 24  ω    103.00 173.00   0.50    0.30    --  111.50  77.00 150.00  140
 25  ω    115.00 167.00   0.50    0.30    --  111.50  30.00  90.00  104
 26  ω    114.00 140.00   0.50    0.30    --  111.50  15.00 -30.00   52
 27  ω    142.00 177.00   0.50    0.30    --  111.50  15.00 -30.00   70
 28  ω     34.00 122.00   0.50    0.05    --   49.53  65.00 179.00  176
 29  ω    -65.00  22.00   0.50    0.05    --  -49.53  65.00 179.00  174
 30  ω    -77.00 -18.00   0.50    0.30    --  -90.00  65.00 179.00  118
 31  ω    -50.00 -18.00   0.50    0.30    --  -90.00  45.00   0.00   64
 32  ω     32.00  57.00   0.50    0.30    --  104.20 -65.00  43.00   50
 33  ω     41.00  66.00   0.50    0.30    --  111.50 -65.00  43.00   50
 34  ω     41.00  66.00   0.50    0.30    --  111.50 -65.00  43.00   50
 35  ω     41.00  66.00   0.50    0.30    --  111.50 -65.00  43.00   50
;
_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      -0.1517307000
_diffrn_orient_matrix_UB_12      0.0251994000
_diffrn_orient_matrix_UB_13      -0.0244646000
_diffrn_orient_matrix_UB_21      -0.0081424000
_diffrn_orient_matrix_UB_22      -0.0642415000
_diffrn_orient_matrix_UB_23      0.0898691000
_diffrn_orient_matrix_UB_31      0.0540079000
_diffrn_orient_matrix_UB_32      0.0611442000
_diffrn_orient_matrix_UB_33      0.1045249000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3813
_reflns_number_total             4037
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.
;
# start Validation Reply Form
_vrf_PLAT906_final               
;
PROBLEM: Large K Value in the Analysis of Variance ...... 2.335 Check 
RESPONSE: The K value is large only for weak reflections with Fc/Fcmax 
lower than 0.015.
;
# end Validation Reply Form

_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.054
_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)+(0.0409P)²+3.1760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C10(H10), C14(H14), C17(H17), C19(H19), C7(H7), C5(H5),
 C18(H18), C12(H12), C13(H13), C8(H8), C11(H11), C4(H4)
;
_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
S2 S 0.60504(5) 0.56087(3) 0.81285(5) 0.02081(14) Uani 1 1 d . . . . .
S1 S 0.50768(6) 0.73530(3) 0.80892(5) 0.02425(14) Uani 1 1 d . . . . .
F1 F 0.40165(14) 0.62864(8) 0.63254(12) 0.0261(3) Uani 1 1 d . . . . .
O4 O 0.69149(16) 0.58722(10) 0.75061(15) 0.0258(3) Uani 1 1 d . . . . .
F2 F -0.21117(15) 0.52049(11) 0.54053(15) 0.0426(4) Uani 1 1 d . . . . .
O5 O 0.65906(17) 0.55758(10) 0.94248(15) 0.0277(4) Uani 1 1 d . . . . .
O3 O 0.62819(18) 0.73238(10) 0.92041(15) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.38134(18) 0.77314(11) 0.80480(17) 0.0326(4) Uani 1 1 d . . . . .
O1 O 0.38107(19) 0.60932(12) 0.91824(15) 0.0354(4) Uani 1 1 d . . . . .
C15 C 0.5258(2) 0.46933(13) 0.7527(2) 0.0212(4) Uani 1 1 d . . . . .
C16 C 0.5329(2) 0.44030(14) 0.6459(2) 0.0236(5) Uani 1 1 d . . . . .
H16 H 0.579577 0.469547 0.604121 0.028 Uiso 1 1 calc R U . . .
C20 C 0.4592(2) 0.42772(14) 0.8168(2) 0.0232(4) Uani 1 1 d . . . . .
H20 H 0.456442 0.448834 0.889893 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5535(2) 0.77616(13) 0.6934(2) 0.0242(5) Uani 1 1 d . . . . .
C1 C 0.4518(2) 0.63056(14) 0.7596(2) 0.0248(5) Uani 1 1 d . . . . .
C10 C 0.4516(2) 0.81632(14) 0.5975(2) 0.0286(5) Uani 1 1 d . . . . .
H10 H 0.357175 0.818075 0.591235 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6924(2) 0.77182(14) 0.7044(2) 0.0286(5) Uani 1 1 d . . . . .
H14 H 0.760319 0.744007 0.770149 0.034 Uiso 1 1 calc R U . . .
C17 C 0.4697(3) 0.36725(15) 0.6019(2) 0.0289(5) Uani 1 1 d . . . . .
H17 H 0.472933 0.345853 0.529128 0.035 Uiso 1 1 calc R U . . .
C19 C 0.3976(2) 0.35538(15) 0.7718(2) 0.0269(5) Uani 1 1 d . . . . .
H19 H 0.352045 0.325857 0.814315 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1963(2) 0.58494(15) 0.7291(2) 0.0266(5) Uani 1 1 d . . . . .
C7 C -0.0210(3) 0.60193(16) 0.5548(2) 0.0315(5) Uani 1 1 d . . . . .
H7 H -0.075756 0.627915 0.480864 0.038 Uiso 1 1 calc R U . . .
C5 C -0.0022(3) 0.50408(15) 0.7104(2) 0.0298(5) Uani 1 1 d . . . . .
H5 H -0.044244 0.463113 0.740359 0.036 Uiso 1 1 calc R U . . .
C6 C -0.0774(2) 0.54227(16) 0.6028(2) 0.0287(5) Uani 1 1 d . . . . .
C18 C 0.4017(3) 0.32539(15) 0.6643(2) 0.0296(5) Uani 1 1 d . . . . .
H18 H 0.357665 0.275799 0.633125 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6291(3) 0.85040(16) 0.5224(2) 0.0335(5) Uani 1 1 d . . . . .
H12 H 0.656008 0.876864 0.464014 0.040 Uiso 1 1 calc R U . . .
C13 C 0.7285(3) 0.80905(15) 0.6171(3) 0.0330(5) Uani 1 1 d . . . . .
H13 H 0.822298 0.806303 0.621931 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1192(3) 0.62276(15) 0.6185(2) 0.0295(5) Uani 1 1 d . . . . .
H8 H 0.162056 0.662403 0.586982 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4911(3) 0.85359(16) 0.5118(2) 0.0333(5) Uani 1 1 d . . . . .
H11 H 0.423525 0.881342 0.445662 0.040 Uiso 1 1 calc R U . . .
C4 C 0.1340(3) 0.52596(15) 0.7738(2) 0.0307(5) Uani 1 1 d . . . . .
H4 H 0.186283 0.500641 0.848975 0.037 Uiso 1 1 calc R U . . .
C2 C 0.3409(3) 0.60851(15) 0.8096(2) 0.0278(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O4 1.4309(16) . ?
S2 O5 1.4279(17) . ?
S2 C15 1.754(2) . ?
S2 C1 1.871(2) . ?
S1 O3 1.4329(17) . ?
S1 O2 1.4349(17) . ?
S1 C9 1.755(2) . ?
S1 C1 1.866(2) . ?
F1 C1 1.400(3) . ?
F2 C6 1.346(3) . ?
O1 C2 1.198(3) . ?
C15 C16 1.389(3) . ?
C15 C20 1.393(3) . ?
C16 C17 1.389(3) . ?
C20 C19 1.376(3) . ?
C9 C10 1.395(3) . ?
C9 C14 1.393(3) . ?
C1 C2 1.525(3) . ?
C10 C11 1.384(4) . ?
C14 C13 1.380(4) . ?
C17 C18 1.390(4) . ?
C19 C18 1.391(3) . ?
C3 C8 1.402(3) . ?
C3 C4 1.390(4) . ?
C3 C2 1.488(3) . ?
C7 C6 1.384(4) . ?
C7 C8 1.400(4) . ?
C5 C6 1.376(4) . ?
C5 C4 1.369(4) . ?
C12 C13 1.385(4) . ?
C12 C11 1.385(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
O4 S2 C15 110.08(10) . . ?
O4 S2 C1 104.40(10) . . ?
O5 S2 O4 120.53(10) . . ?
O5 S2 C15 109.68(10) . . ?
O5 S2 C1 108.73(10) . . ?
C15 S2 C1 101.63(10) . . ?
O3 S1 O2 120.30(11) . . ?
O3 S1 C9 109.88(11) . . ?
O3 S1 C1 108.35(10) . . ?
O2 S1 C9 108.44(11) . . ?
O2 S1 C1 103.53(11) . . ?
C9 S1 C1 105.20(11) . . ?
C16 C15 S2 119.94(17) . . ?
C16 C15 C20 122.5(2) . . ?
C20 C15 S2 117.57(17) . . ?
C15 C16 C17 118.1(2) . . ?
C19 C20 C15 118.5(2) . . ?
C10 C9 S1 118.90(18) . . ?
C14 C9 S1 118.90(18) . . ?
C14 C9 C10 122.1(2) . . ?
S1 C1 S2 110.89(12) . . ?
F1 C1 S2 105.53(14) . . ?
F1 C1 S1 107.69(15) . . ?
F1 C1 C2 113.17(18) . . ?
C2 C1 S2 112.51(16) . . ?
C2 C1 S1 107.01(16) . . ?
C11 C10 C9 118.5(2) . . ?
C13 C14 C9 118.2(2) . . ?
C16 C17 C18 120.1(2) . . ?
C20 C19 C18 120.1(2) . . ?
C8 C3 C2 123.8(2) . . ?
C4 C3 C8 119.9(2) . . ?
C4 C3 C2 116.0(2) . . ?
C6 C7 C8 117.9(2) . . ?
C4 C5 C6 119.1(2) . . ?
F2 C6 C7 118.3(2) . . ?
F2 C6 C5 118.9(2) . . ?
C5 C6 C7 122.8(2) . . ?
C17 C18 C19 120.7(2) . . ?
C11 C12 C13 120.7(2) . . ?
C14 C13 C12 120.5(2) . . ?
C7 C8 C3 119.8(2) . . ?
C10 C11 C12 120.0(2) . . ?
C5 C4 C3 120.5(2) . . ?
O1 C2 C1 114.6(2) . . ?
O1 C2 C3 123.2(2) . . ?
C3 C2 C1 122.1(2) . . ?

_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 1.222
_oxdiff_exptl_absorpt_empirical_full_min 0.874
####################################################################### 
# 
# 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_final_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 2427902'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-28 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Br F O5 S2'
_chemical_formula_sum            'C20 H14 Br F O5 S2'
_chemical_formula_weight         497.34
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O5FBr
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'
Br Br -0.6763 1.2805 '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'

_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                   7.95350(10)
_cell_length_b                   13.9305(2)
_cell_length_c                   8.81110(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.1920(10)
_cell_angle_gamma                90
_cell_volume                     975.52(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8905
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.5290
_cell_measurement_theta_min      3.2440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.064
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10509
_diffrn_reflns_point_group_measured_fraction_full 0.841
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.922
_diffrn_reflns_theta_min         5.023
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  22.00   0.50    0.05    --  -49.66  93.00  97.00  198
  2  ω    -80.00 -18.00   0.50    0.10    --  -90.00  93.00  97.00  124
  3  ω    -50.00 -18.00   0.50    0.10    --  -90.00  45.00 -60.00   64
  4  ω    -50.00 -18.00   0.50    0.10    --  -90.00  45.00 -90.00   64
  5  ω   -120.00 -82.00   0.50    0.05    --  -49.66 -57.00 -60.00   76
  6  ω   -120.00 -82.00   0.50    0.05    --  -49.66 -57.00   0.00   76
  7  ω   -120.00 -82.00   0.50    0.05    --  -49.66 -57.00 -30.00   76
  8  ω   -161.00 -83.00   0.50    0.10    --  -90.00 -93.00 -14.00  156
  9  ω   -118.00 -87.00   0.50    0.05    --  -49.66-125.00 150.00   62
 10  ω     41.00 106.00   0.50    0.10    --  111.50 -77.00-120.00  130
 11  ω     41.00 106.00   0.50    0.10    --  111.50 -77.00-120.00  130
 12  ω     43.00  75.00   0.50    0.10    --  111.50 -77.00-150.00   64
 13  ω     41.00  71.00   0.50    0.10    --  111.50 -61.00 -90.00   60
 14  ω     41.00  71.00   0.50    0.10    --  111.50 -61.00 -30.00   60
 15  ω     41.00  72.00   0.50    0.10    --  111.50 -61.00-120.00   62
 16  ω     43.00  70.00   0.50    0.10    --  111.50 -61.00   0.00   54
 17  ω     41.00  68.00   0.50    0.10    --  111.50 -61.00  60.00   54
 18  ω     41.00  71.00   0.50    0.10    --  111.50 -61.00 120.00   60
 19  ω     45.00  94.00   0.50    0.10    --  111.50-125.00 150.00   98
 20  ω     68.00 104.00   0.50    0.10    --  111.50 -95.00 120.00   72
 21  ω     49.00  75.00   0.50    0.10    --  111.50 -95.00  30.00   52
 22  ω     41.00 106.00   0.50    0.10    --  111.50 -93.00 -14.00  130
 23  ω    -13.00  78.00   0.50    0.05    --   49.66 -93.00 -14.00  182
 24  ω     41.00 105.00   0.50    0.10    --  111.50 -95.00-150.00  128
 25  ω     41.00 105.00   0.50    0.10    --  111.50 -95.00-180.00  128
 26  ω    102.00 173.00   0.50    0.10    --  111.50  45.00 -60.00  142
 27  ω    122.00 176.00   0.50    0.10    --  111.50 125.00-180.00  108
 28  ω    122.00 176.00   0.50    0.10    --  111.50 125.00-180.00  108
 29  ω     82.00 121.00   0.50    0.05    --   49.66  57.00 -90.00   78
 30  ω    104.00 178.00   0.50    0.10    --  111.50  93.00  97.00  148
;
_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      0.1143357000
_diffrn_orient_matrix_UB_12      -0.0771038000
_diffrn_orient_matrix_UB_13      -0.0672058000
_diffrn_orient_matrix_UB_21      -0.1528348000
_diffrn_orient_matrix_UB_22      -0.0670318000
_diffrn_orient_matrix_UB_23      -0.0238234000
_diffrn_orient_matrix_UB_31      -0.0336341000
_diffrn_orient_matrix_UB_32      0.0423620000
_diffrn_orient_matrix_UB_33      -0.1597971000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.609
_reflns_number_gt                3383
_reflns_number_total             3406
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.027
_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)+(0.0388P)²+0.4710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C20(H20), C7(H7), C18(H18),
 C13(H13), C12(H12), C16(H16), C19(H19), C17(H17), C8(H8)
;
_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
Br1 Br 0.95103(5) 0.11042(3) 0.96329(4) 0.03185(13) Uani 1 1 d . . . . .
S1 S 0.78489(9) 0.63298(6) 0.47061(8) 0.01628(17) Uani 1 1 d . . . . .
S2 S 0.48614(9) 0.58862(6) 0.67735(8) 0.01572(17) Uani 1 1 d . . . . .
F1 F 0.8014(2) 0.57103(15) 0.75065(19) 0.0183(4) Uani 1 1 d . . . . .
O1 O 0.6263(3) 0.43438(19) 0.4491(2) 0.0199(5) Uani 1 1 d . . . . .
O3 O 0.6454(3) 0.6648(2) 0.3760(3) 0.0222(5) Uani 1 1 d . . . . .
O5 O 0.3673(3) 0.5586(2) 0.5614(3) 0.0232(6) Uani 1 1 d . . . . .
O4 O 0.4987(3) 0.6879(2) 0.7205(3) 0.0228(5) Uani 1 1 d . . . . .
O2 O 0.9170(3) 0.5771(2) 0.4088(3) 0.0246(5) Uani 1 1 d . . . . .
C2 C 0.7021(4) 0.4494(3) 0.5687(4) 0.0167(6) Uani 1 1 d . . . . .
C4 C 0.7050(4) 0.2804(3) 0.6422(4) 0.0206(7) Uani 1 1 d . . . . .
H4 H 0.619447 0.272089 0.565120 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7766(4) 0.3707(3) 0.6645(4) 0.0170(7) Uani 1 1 d . . . . .
C5 C 0.7556(4) 0.2028(3) 0.7296(4) 0.0205(7) Uani 1 1 d . . . . .
H5 H 0.704300 0.141810 0.714594 0.025 Uiso 1 1 calc R U . . .
C10 C 1.0364(4) 0.7177(3) 0.6360(4) 0.0195(7) Uani 1 1 d . . . . .
H10 H 1.095582 0.659053 0.624312 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8826(4) 0.2155(3) 0.8397(4) 0.0227(7) Uani 1 1 d . . . . .
C1 C 0.7016(4) 0.5540(3) 0.6224(3) 0.0162(6) Uani 1 1 d . . . . .
C11 C 1.1084(4) 0.7933(3) 0.7170(4) 0.0219(7) Uani 1 1 d . . . . .
H11 H 1.217410 0.786276 0.763574 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7856(4) 0.8155(3) 0.5852(4) 0.0193(7) Uani 1 1 d . . . . .
H14 H 0.675103 0.822119 0.541659 0.023 Uiso 1 1 calc R U . . .
C20 C 0.4054(4) 0.4237(3) 0.8214(4) 0.0230(7) Uani 1 1 d . . . . .
H20 H 0.361225 0.402038 0.725700 0.028 Uiso 1 1 calc R U . . .
C15 C 0.4677(4) 0.5162(3) 0.8387(4) 0.0172(6) Uani 1 1 d . . . . .
C7 C 0.9605(5) 0.3036(3) 0.8613(4) 0.0281(8) Uani 1 1 d . . . . .
H7 H 1.049635 0.310815 0.935358 0.034 Uiso 1 1 calc R U . . .
C9 C 0.8742(4) 0.7298(3) 0.5719(4) 0.0172(6) Uani 1 1 d . . . . .
C18 C 0.4713(5) 0.3972(3) 1.0869(5) 0.0310(9) Uani 1 1 d . . . . .
H18 H 0.473774 0.355770 1.172549 0.037 Uiso 1 1 calc R U . . .
C13 C 0.8625(5) 0.8904(3) 0.6633(4) 0.0224(7) Uani 1 1 d . . . . .
H13 H 0.805695 0.950119 0.671064 0.027 Uiso 1 1 calc R U . . .
C12 C 1.0221(4) 0.8795(3) 0.7307(4) 0.0208(7) Uani 1 1 d . . . . .
H12 H 1.072538 0.931101 0.786383 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5289(4) 0.5508(3) 0.9784(4) 0.0235(7) Uani 1 1 d . . . . .
H16 H 0.569533 0.614700 0.988274 0.028 Uiso 1 1 calc R U . . .
C19 C 0.4092(5) 0.3634(3) 0.9470(5) 0.0288(8) Uani 1 1 d . . . . .
H19 H 0.369508 0.299275 0.937545 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5291(5) 0.4900(4) 1.1028(4) 0.0301(9) Uani 1 1 d . . . . .
H17 H 0.569249 0.512323 1.199341 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9071(5) 0.3808(3) 0.7740(4) 0.0262(8) Uani 1 1 d . . . . .
H8 H 0.959628 0.441571 0.788483 0.031 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
Br1 C6 1.892(4) . ?
S1 O3 1.432(3) . ?
S1 O2 1.432(3) . ?
S1 C1 1.873(3) . ?
S1 C9 1.753(4) . ?
S2 O5 1.428(2) . ?
S2 O4 1.436(3) . ?
S2 C1 1.862(3) . ?
S2 C15 1.754(3) . ?
F1 C1 1.377(3) . ?
O1 C2 1.212(4) . ?
C2 C3 1.493(5) . ?
C2 C1 1.531(5) . ?
C4 C3 1.391(5) . ?
C4 C5 1.378(5) . ?
C3 C8 1.397(5) . ?
C5 C6 1.385(5) . ?
C10 C11 1.385(5) . ?
C10 C9 1.398(5) . ?
C6 C7 1.384(6) . ?
C11 C12 1.390(6) . ?
C14 C9 1.394(5) . ?
C14 C13 1.381(5) . ?
C20 C15 1.387(5) . ?
C20 C19 1.389(5) . ?
C15 C16 1.393(5) . ?
C7 C8 1.380(6) . ?
C18 C19 1.392(6) . ?
C18 C17 1.376(7) . ?
C13 C12 1.389(5) . ?
C16 C17 1.385(6) . ?

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
O3 S1 C1 108.06(15) . . ?
O3 S1 C9 110.37(16) . . ?
O2 S1 O3 120.67(15) . . ?
O2 S1 C1 103.70(15) . . ?
O2 S1 C9 108.85(15) . . ?
C9 S1 C1 103.68(15) . . ?
O5 S2 O4 120.61(16) . . ?
O5 S2 C1 109.16(15) . . ?
O5 S2 C15 109.74(16) . . ?
O4 S2 C1 105.27(16) . . ?
O4 S2 C15 110.25(16) . . ?
C15 S2 C1 99.67(15) . . ?
O1 C2 C3 122.5(3) . . ?
O1 C2 C1 115.2(3) . . ?
C3 C2 C1 122.0(3) . . ?
C5 C4 C3 121.4(3) . . ?
C4 C3 C2 115.6(3) . . ?
C4 C3 C8 118.6(3) . . ?
C8 C3 C2 125.8(3) . . ?
C4 C5 C6 118.7(4) . . ?
C11 C10 C9 118.2(4) . . ?
C5 C6 Br1 119.4(3) . . ?
C7 C6 Br1 119.3(3) . . ?
C7 C6 C5 121.4(3) . . ?
S2 C1 S1 112.81(18) . . ?
F1 C1 S1 106.0(2) . . ?
F1 C1 S2 104.4(2) . . ?
F1 C1 C2 114.2(3) . . ?
C2 C1 S1 109.5(2) . . ?
C2 C1 S2 109.9(2) . . ?
C10 C11 C12 120.4(3) . . ?
C13 C14 C9 118.3(3) . . ?
C15 C20 C19 118.5(3) . . ?
C20 C15 S2 119.1(3) . . ?
C20 C15 C16 122.0(3) . . ?
C16 C15 S2 118.7(3) . . ?
C8 C7 C6 119.2(3) . . ?
C10 C9 S1 117.6(3) . . ?
C14 C9 S1 120.4(3) . . ?
C14 C9 C10 122.1(3) . . ?
C17 C18 C19 120.9(4) . . ?
C14 C13 C12 120.7(4) . . ?
C13 C12 C11 120.2(3) . . ?
C17 C16 C15 118.5(4) . . ?
C20 C19 C18 119.8(4) . . ?
C18 C17 C16 120.2(4) . . ?
C7 C8 C3 120.7(4) . . ?

_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 1.702
_oxdiff_exptl_absorpt_empirical_full_min 0.653
####################################################################### 
# 
# 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_final_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 2427889'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F I O5 S2'
_chemical_formula_sum            'C20 H14 F I O5 S2'
_chemical_formula_weight         544.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O5FI
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'
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'
S S 0.3331 0.5567 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.2647(3)
_cell_length_b                   8.0423(2)
_cell_length_c                   14.3794(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.135(2)
_cell_angle_gamma                90
_cell_volume                     1991.35(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13538
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5550
_cell_measurement_theta_min      2.5460
_shelx_estimated_absorpt_T_max   0.346
_shelx_estimated_absorpt_T_min   0.213
_exptl_absorpt_coefficient_mu    14.958
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 -2 0.0553
2 -1 2 0.0762
-2 1 -2 0.0679
-1 2 -1 0.0569
1 -2 1 0.0668
-1 1 -1 0.0505
0 1 -1 0.0453
-1 0 2 0.1096
1 0 -2 0.0184
1 2 0 0.0506
1 1 -1 0.0341
-1 -1 1 0.1048
-2 0 1 0.0982
2 0 -1 0.0060
2 -1 0 0.0200
-2 1 0 0.0728
2 1 1 0.0372
-2 -1 -1 0.0877

_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.093
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
-0.9869 -2.0002 -2.0002 -0.0938 -0.0212 0.4403
1.9979 -0.9971 2.0057 0.3355 0.0149 0.0885
-1.9979 0.9971 -2.0057 -0.3355 -0.0149 -0.0885
-1.0048 1.9975 -1.0041 -0.2596 -0.0378 -0.3147
1.0048 -1.9975 1.0041 0.2596 0.0378 0.3147
-1.0009 0.9982 -1.0033 -0.1984 -0.0175 -0.1344
-0.0014 0.9989 -1.0002 -0.1403 -0.0844 -0.1464
-1.0043 0.0002 1.9958 0.1000 0.1954 -0.0557
1.0043 -0.0002 -1.9958 -0.1000 -0.1954 0.0557
0.9917 1.9993 0.0014 -0.0643 -0.1073 -0.3726
0.9980 0.9996 -0.9972 -0.0822 -0.1513 -0.1585
-0.9980 -0.9996 0.9972 0.0822 0.1513 0.1585
-2.0014 -0.0009 0.9934 -0.0372 0.1980 -0.0098
2.0014 0.0009 -0.9934 0.0372 -0.1980 0.0098
2.0028 -0.9980 0.0068 0.1774 -0.1136 0.1562
-2.0028 0.9980 -0.0068 -0.1774 0.1136 -0.1562
1.9926 1.0011 1.0046 0.1341 -0.0898 -0.2382
-1.9926 -1.0011 -1.0046 -0.1341 0.0898 0.2382

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20346
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         80.530
_diffrn_reflns_theta_min         2.566
_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 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     60.00 103.00   0.50    0.45    --  111.50 -95.00  60.00   86
  2  ω     49.00 105.00   0.50    0.45    --  111.50 -95.00   0.00  112
  3  ω     59.00  92.00   0.50    0.45    --  111.50 -95.00 -30.00   66
  4  ω     70.00  95.00   0.50    0.45    --  111.50 -95.00-150.00   50
  5  ω     73.00  99.00   0.50    0.45    --  111.50-125.00 -60.00   52
  6  ω     50.00 105.00   0.50    0.45    --  111.50 -95.00 120.00  110
  7  ω     60.00  93.00   0.50    0.45    --  111.50 -77.00   0.00   66
  8  ω     42.00  71.00   0.50    0.45    --  111.50 -61.00  30.00   58
  9  ω     44.00  71.00   0.50    0.45    --  111.50 -61.00 120.00   54
 10  ω     44.00  72.00   0.50    0.45    --  111.50 -61.00 150.00   56
 11  ω     42.00  72.00   0.50    0.45    --  111.50 -61.00   0.00   60
 12  ω    -18.00  26.00   0.50    0.15    --   49.53 -26.00 116.00   88
 13  ω     41.00  67.00   0.50    0.45    --  111.50 -61.00 -90.00   52
 14  ω     46.00  71.00   0.50    0.45    --  111.50 -61.00-150.00   50
 15  ω     42.00  68.00   0.50    0.45    --  111.50 -61.00-180.00   52
 16  ω    123.00 171.00   0.50    0.45    --  111.50  15.00 -30.00   96
 17  ω    118.00 175.00   0.50    0.45    --  111.50  30.00 -60.00  114
 18  ω    107.00 166.00   0.50    0.45    --  111.50  61.00   0.00  118
 19  ω    104.00 166.00   0.50    0.45    --  111.50  26.00 -79.00  124
 20  ω    111.00 178.00   0.50    0.45    --  111.50  61.00-150.00  134
 21  ω    103.00 150.00   0.50    0.45    --  111.50  45.00-180.00   94
 22  ω     64.00  93.00   0.50    0.15    --   49.53  26.00 -79.00   58
 23  ω    -25.00  23.00   0.50    0.15    --  -49.53  19.00 120.00   96
 24  ω    -57.00 -21.00   0.50    0.45    --  -90.00  61.00  90.00   72
 25  ω    -50.00 -24.00   0.50    0.45    --  -90.00  45.00 -90.00   52
 26  ω    -30.00  -1.00   0.50    0.15    --  -49.53  26.00 -79.00   58
 27  ω    -23.00  20.00   0.50    0.15    --  -49.53  19.00  60.00   86
 28  ω   -123.00 -43.00   0.50    0.15    --  -49.53 -26.00 116.00  160
 29  ω   -159.00-122.00   0.50    0.45    --  -90.00 -26.00 116.00   74
 30  ω   -118.00 -87.00   0.50    0.15    --  -49.53-125.00-150.00   62
 31  ω   -114.00 -88.00   0.50    0.45    --  -90.00 -26.00 116.00   52
 32  ω     41.00  66.00   0.50    0.45    --  111.50 -61.00  60.00   50
 33  ω   -106.00 -81.00   0.50    0.15    --  -49.78 -26.00 116.00   50
 34  ω   -121.00 -42.00   0.50    0.15    --  -49.78 -38.00  30.00  158
 35  ω   -121.00 -42.00   0.50    0.15    --  -49.78 -38.00-150.00  158
 36  ω     34.00  70.00   0.50    0.15    --   49.78-125.00 -30.00   72
 37  ω     42.00 121.00   0.50    0.15    --   49.78  38.00 -30.00  158
;
_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      0.0579395000
_diffrn_orient_matrix_UB_12      -0.0609655000
_diffrn_orient_matrix_UB_13      0.0792693000
_diffrn_orient_matrix_UB_21      -0.0671109000
_diffrn_orient_matrix_UB_22      -0.0204272000
_diffrn_orient_matrix_UB_23      0.0641174000
_diffrn_orient_matrix_UB_31      -0.0118077000
_diffrn_orient_matrix_UB_32      -0.1804862000
_diffrn_orient_matrix_UB_33      -0.0338204000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3781
_reflns_number_total             4226
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         1.122
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.075
_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)+(0.0424P)²+4.1536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0953
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C14(H14), C13(H13), C20(H20), C8(H8), C12(H12), C10(H10),
 C7(H7), C19(H19), C11(H11), C18(H18), C16(H16), C17(H17)
;
_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 0.43665(2) 0.86507(3) 0.69704(2) 0.03871(10) Uani 1 1 d . . . . .
S2 S 0.79755(5) 0.80124(10) 0.33458(6) 0.02366(17) Uani 1 1 d . . . . .
S1 S 0.84379(5) 0.50096(10) 0.46453(6) 0.02484(18) Uani 1 1 d . . . . .
F1 F 0.79352(11) 0.7913(2) 0.51384(14) 0.0258(4) Uani 1 1 d . . . . .
O5 O 0.74366(14) 0.9365(3) 0.33941(18) 0.0295(5) Uani 1 1 d . . . . .
O3 O 0.90991(15) 0.5672(3) 0.5178(2) 0.0378(6) Uani 1 1 d . . . . .
O4 O 0.79329(16) 0.6941(3) 0.25485(17) 0.0330(6) Uani 1 1 d . . . . .
O1 O 0.67375(15) 0.5465(3) 0.36131(17) 0.0292(5) Uani 1 1 d . . . . .
O2 O 0.85121(16) 0.4197(3) 0.37711(18) 0.0323(6) Uani 1 1 d . . . . .
C5 C 0.5979(2) 0.7612(4) 0.6499(3) 0.0267(7) Uani 1 1 d . . . . .
H5 H 0.610656 0.780799 0.714380 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6360(2) 0.6821(4) 0.4977(2) 0.0242(7) Uani 1 1 d . . . . .
C6 C 0.5222(2) 0.7806(5) 0.6127(2) 0.0268(7) Uani 1 1 d . . . . .
C9 C 0.7919(2) 0.3707(4) 0.5363(2) 0.0230(7) Uani 1 1 d . . . . .
C2 C 0.69192(19) 0.6274(4) 0.4288(2) 0.0218(7) Uani 1 1 d . . . . .
C4 C 0.6555(2) 0.7124(4) 0.5916(2) 0.0261(7) Uani 1 1 d . . . . .
H4 H 0.707687 0.700094 0.616216 0.031 Uiso 1 1 calc R U . . .
C15 C 0.8930(2) 0.8770(4) 0.3536(2) 0.0252(7) Uani 1 1 d . . . . .
C14 C 0.7429(2) 0.2501(4) 0.4957(2) 0.0247(7) Uani 1 1 d . . . . .
H14 H 0.734901 0.242197 0.429816 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7059(2) 0.1410(4) 0.5528(3) 0.0284(7) Uani 1 1 d . . . . .
H13 H 0.672404 0.057183 0.526144 0.034 Uiso 1 1 calc R U . . .
C20 C 0.9053(2) 1.0332(4) 0.3921(3) 0.0300(8) Uani 1 1 d . . . . .
H20 H 0.863395 1.095063 0.413982 0.036 Uiso 1 1 calc R U . . .
C1 C 0.77793(19) 0.6804(4) 0.4413(2) 0.0230(7) Uani 1 1 d . . . . .
C8 C 0.5592(2) 0.6956(5) 0.4623(3) 0.0350(8) Uani 1 1 d . . . . .
H8 H 0.545533 0.669364 0.398817 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7179(2) 0.1549(4) 0.6488(3) 0.0328(8) Uani 1 1 d . . . . .
H12 H 0.693096 0.079247 0.687805 0.039 Uiso 1 1 calc R U . . .
C10 C 0.8030(2) 0.3876(4) 0.6324(3) 0.0318(8) Uani 1 1 d . . . . .
H10 H 0.835571 0.472672 0.659311 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5023(2) 0.7473(6) 0.5194(3) 0.0378(9) Uani 1 1 d . . . . .
H7 H 0.450122 0.759915 0.494694 0.045 Uiso 1 1 calc R U . . .
C19 C 0.9800(3) 1.0982(5) 0.3983(3) 0.0388(9) Uani 1 1 d . . . . .
H19 H 0.989824 1.205010 0.424741 0.047 Uiso 1 1 calc R U . . .
C11 C 0.7655(3) 0.2776(5) 0.6883(3) 0.0360(9) Uani 1 1 d . . . . .
H11 H 0.772608 0.286805 0.754199 0.043 Uiso 1 1 calc R U . . .
C18 C 1.0402(2) 1.0056(6) 0.3655(3) 0.0447(11) Uani 1 1 d . . . . .
H18 H 1.091412 1.049775 0.369858 0.054 Uiso 1 1 calc R U . . .
C16 C 0.9530(2) 0.7831(5) 0.3207(3) 0.0383(9) Uani 1 1 d . . . . .
H16 H 0.943476 0.675704 0.294847 0.046 Uiso 1 1 calc R U . . .
C17 C 1.0268(3) 0.8509(6) 0.3268(3) 0.0473(11) Uani 1 1 d . . . . .
H17 H 1.068649 0.789960 0.304105 0.057 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 C6 2.091(3) . ?
S2 O5 1.436(3) . ?
S2 O4 1.432(3) . ?
S2 C15 1.759(4) . ?
S2 C1 1.867(3) . ?
S1 O3 1.431(3) . ?
S1 O2 1.431(3) . ?
S1 C9 1.760(3) . ?
S1 C1 1.853(3) . ?
F1 C1 1.384(4) . ?
O1 C2 1.191(4) . ?
C5 C6 1.384(5) . ?
C5 C4 1.403(5) . ?
C3 C2 1.499(5) . ?
C3 C4 1.388(5) . ?
C3 C8 1.391(5) . ?
C6 C7 1.387(5) . ?
C9 C14 1.387(5) . ?
C9 C10 1.388(5) . ?
C2 C1 1.543(5) . ?
C15 C20 1.384(5) . ?
C15 C16 1.392(5) . ?
C14 C13 1.389(5) . ?
C13 C12 1.385(6) . ?
C20 C19 1.388(5) . ?
C8 C7 1.388(5) . ?
C12 C11 1.380(6) . ?
C10 C11 1.386(6) . ?
C19 C18 1.389(7) . ?
C18 C17 1.376(7) . ?
C16 C17 1.384(6) . ?

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
O5 S2 C15 109.43(16) . . ?
O5 S2 C1 101.41(15) . . ?
O4 S2 O5 119.90(17) . . ?
O4 S2 C15 109.05(16) . . ?
O4 S2 C1 110.06(15) . . ?
C15 S2 C1 105.99(16) . . ?
O3 S1 O2 121.45(17) . . ?
O3 S1 C9 109.16(18) . . ?
O3 S1 C1 105.18(16) . . ?
O2 S1 C9 108.96(16) . . ?
O2 S1 C1 106.86(16) . . ?
C9 S1 C1 103.74(15) . . ?
C6 C5 C4 119.3(3) . . ?
C4 C3 C2 124.9(3) . . ?
C4 C3 C8 120.0(3) . . ?
C8 C3 C2 115.1(3) . . ?
C5 C6 I1 119.9(3) . . ?
C5 C6 C7 120.9(3) . . ?
C7 C6 I1 119.2(3) . . ?
C14 C9 S1 119.3(3) . . ?
C14 C9 C10 121.6(3) . . ?
C10 C9 S1 119.1(3) . . ?
O1 C2 C3 123.7(3) . . ?
O1 C2 C1 116.2(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C4 C5 119.9(3) . . ?
C20 C15 S2 119.5(3) . . ?
C20 C15 C16 122.1(4) . . ?
C16 C15 S2 118.1(3) . . ?
C9 C14 C13 119.1(3) . . ?
C12 C13 C14 119.7(3) . . ?
C15 C20 C19 118.9(4) . . ?
S1 C1 S2 114.09(17) . . ?
F1 C1 S2 104.3(2) . . ?
F1 C1 S1 106.4(2) . . ?
F1 C1 C2 113.5(3) . . ?
C2 C1 S2 106.1(2) . . ?
C2 C1 S1 112.2(2) . . ?
C7 C8 C3 120.2(4) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C10 C9 118.5(4) . . ?
C6 C7 C8 119.6(4) . . ?
C20 C19 C18 119.5(4) . . ?
C12 C11 C10 120.5(4) . . ?
C17 C18 C19 120.9(4) . . ?
C17 C16 C15 118.0(4) . . ?
C18 C17 C16 120.6(4) . . ?

_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 1.894
_oxdiff_exptl_absorpt_empirical_full_min 0.614
####################################################################### 
# 
# 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_final3
_database_code_depnum_ccdc_archive 'CCDC 2427887'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C41 H55 F O6 S2'
_chemical_formula_sum            'C41 H55 F O6 S2'
_chemical_formula_weight         726.97
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H52S2O5F
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'

_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                   9.6794(5)
_cell_length_b                   11.5261(8)
_cell_length_c                   17.4102(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.176(6)
_cell_angle_gamma                90
_cell_volume                     1922.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9015
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      78.3210
_cell_measurement_theta_min      2.5690
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             780
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 1 0.0213
-2 1 2 0.0286
2 -1 -2 0.0534
1 1 1 0.0386
0 -1 2 0.0181
0 1 -2 0.0141
-1 -2 -2 0.0241

_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.032
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
-1.0221 1.9989 0.8918 -0.2292 0.0188 -0.2187
-2.0372 1.0020 1.8276 -0.0688 -0.0166 -0.3626
2.0372 -1.0020 -1.8276 0.0688 0.0166 0.3626
0.9641 1.0121 1.0789 -0.1734 -0.1344 0.0885
-0.0487 -0.9834 2.0293 0.1170 -0.1878 -0.0305
0.0487 0.9834 -2.0293 -0.1170 0.1878 0.0305
-0.9362 -2.0183 -2.0715 0.3097 0.2013 -0.0358

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20087
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.824
_diffrn_reflns_theta_min         2.564
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  -7.00   0.50   10.00    --  -49.28 112.00-141.00  150
  2  ω     52.00  78.00   0.50   10.00    --   49.28-112.00 126.00   52
  3  ω    -58.00 -32.00   0.50   45.00    --  -90.00 112.00-141.00   52
  4  ω   -137.00-111.00   0.50   45.00    --  -90.00-112.00 126.00   52
  5  ω    104.00 146.00   0.50   45.00    --  111.50 112.00-141.00   84
  6  ω     71.00 103.00   0.50   45.00    --  111.50-112.00 126.00   64
  7  ω   -121.00 -82.00   0.50   10.00    --  -49.28 -57.00  90.00   78
  8  ω   -115.00 -83.00   0.50   10.00    --  -49.28 -57.00-150.00   64
  9  ω    -25.00  23.00   0.50   10.00    --  -49.28  19.00 150.00   96
 10  ω   -121.00 -82.00   0.50   10.00    --  -49.28 -57.00-180.00   78
 11  ω    -50.00 -25.00   0.50   45.00    --  -90.00  45.00  30.00   50
 12  ω    -44.00 -19.00   0.50   45.00    --  -90.00  45.00   0.00   50
 13  ω    -50.00 -25.00   0.50   45.00    --  -90.00  45.00 150.00   50
 14  ω     42.00  76.00   0.50   45.00    --  111.50 -77.00-180.00   68
 15  ω     41.00  70.00   0.50   45.00    --  111.50 -95.00-180.00   58
 16  ω     41.00  71.00   0.50   45.00    --  111.50 -61.00 -60.00   60
 17  ω     74.00 104.00   0.50   45.00    --  111.50 -95.00-150.00   60
 18  ω     71.00  96.00   0.50   45.00    --  111.50 -95.00-180.00   50
 19  ω    103.00 145.00   0.50   45.00    --  111.50  77.00 -90.00   84
 20  ω    151.00 178.00   0.50   45.00    --  111.50  77.00 -90.00   54
 21  ω     42.00 105.00   0.50   45.00    --  111.50 -95.00 120.00  126
 22  ω    103.00 151.00   0.50   45.00    --  111.50  45.00  30.00   96
 23  ω    106.00 176.00   0.50   45.00    --  111.50  45.00-150.00  140
 24  ω     44.00  72.00   0.50   45.00    --  111.50 -61.00-180.00   56
 25  ω     44.00  71.00   0.50   45.00    --  111.50 -61.00-120.00   54
 26  ω     42.00  68.00   0.50   45.00    --  111.50 -61.00-150.00   52
 27  ω    138.00 177.00   0.50   45.00    --  111.50  15.00-180.00   78
 28  ω     70.00  95.00   0.50   45.00    --  111.50 -95.00-120.00   50
 29  ω     41.00  69.00   0.50   45.00    --  111.50 -61.00  30.00   56
 30  ω     73.00  98.00   0.50   45.00    --  111.50 -95.00 150.00   50
 31  ω     41.00  89.00   0.50   45.00    --  111.50 -95.00  30.00   96
 32  ω     42.00  69.00   0.50   45.00    --  111.50 -61.00 -30.00   54
 33  ω     51.00  77.00   0.50   90.00    --  104.20-112.00 126.00   52
 34  ω   -116.00 -85.00   0.50   20.00    --  -49.78 -57.00   0.00   62
 35  ω     -6.00  22.00   0.50   20.00    --  -49.78  57.00  90.00   56
 36  ω   -117.00 -91.00   0.50   20.00    --  -49.78-125.00  60.00   52
 37  ω   -119.00 -93.00   0.50   20.00    --  -49.78 -57.00  60.00   52
 38  ω    -61.00 -13.00   0.50   20.00    --  -49.78  57.00  90.00   96
 39  ω     87.00 118.00   0.50   20.00    --   49.78  57.00 -60.00   62
 40  ω    -17.00  26.00   0.50   20.00    --   49.78 -19.00-120.00   86
 41  ω    -55.00 -28.00   0.50   90.00    --  -90.00  57.00-150.00   54
 42  ω   -151.00-108.00   0.50   90.00    --  -90.00 -77.00  60.00   86
 43  ω   -161.00-102.00   0.50   90.00    --  -90.00 -77.00  30.00  118
 44  ω    -78.00 -30.00   0.50   90.00    --  -90.00 125.00  90.00   96
 45  ω    -64.00 -18.00   0.50   90.00    --  -90.00  57.00 -60.00   92
 46  ω   -140.00 -87.00   0.50   90.00    --  -90.00-125.00 -60.00  106
 47  ω     85.00 111.00   0.50   20.00    --   49.78  19.00  30.00   52
 48  ω     52.00  73.50   0.50   20.00    --   49.78-125.00-180.00   43
;
_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      -0.0359898000
_diffrn_orient_matrix_UB_12      -0.1302510000
_diffrn_orient_matrix_UB_13      -0.0063267000
_diffrn_orient_matrix_UB_21      -0.0607474000
_diffrn_orient_matrix_UB_22      0.0166694000
_diffrn_orient_matrix_UB_23      -0.0859418000
_diffrn_orient_matrix_UB_31      0.1444803000
_diffrn_orient_matrix_UB_32      -0.0249819000
_diffrn_orient_matrix_UB_33      -0.0236624000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                6097
_reflns_number_total             7410
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.
;
# start Validation Reply Form
_vrf_PLAT906_final3              
;
PROBLEM: Large K Value in the Analysis of Variance ...... 2.191 Check 
RESPONSE: The K value is large only for weak reflections with
Fc/Fcmax lower than 0.018.
;
# end Validation Reply Form
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 2118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         7410
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.040
_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)+(0.0777P)²+1.2014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1571
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C29(H29), C33(H33), C15(H15), C25(H25), C34(H34), C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C36(H36A,H36B), C16(H16A,H16B), C37(H37A,H37B), C19(H19A,
 H19B), C32(H32A,H32B), C20(H20A,H20B), C26(H26A,H26B), C38(H38A,H38B),
 C31(H31A,H31B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C12(H12), C11(H11), C10(H10), C8(H8), C6(H6), C4(H4), C14(H14),
 C7(H7), C5(H5), C13(H13)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C30(H30A,H30B,H30C), C41(H41A,H41B,H41C), C40(H40A,H40B,
 H40C), C35(H35A,H35B,H35C)
;
_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
S2 S 0.18535(13) 0.56967(13) 1.06362(8) 0.0345(3) Uani 1 1 d . . . . .
S1 S -0.05310(13) 0.54195(12) 0.91523(8) 0.0336(3) Uani 1 1 d . . . . .
F1 F 0.0463(3) 0.7296(3) 0.98254(19) 0.0338(7) Uani 1 1 d . . . . .
O2 O 0.2530(4) 0.5344(3) 0.8941(2) 0.0330(8) Uani 1 1 d . . . . .
O6 O 0.2785(4) 0.6637(4) 1.0875(3) 0.0459(11) Uani 1 1 d . . . . .
O3 O -0.0766(4) 0.5998(4) 0.8423(2) 0.0445(11) Uani 1 1 d . . . . .
O4 O -0.0190(4) 0.4218(4) 0.9205(3) 0.0454(11) Uani 1 1 d . . . . .
O1 O 0.2398(4) 0.7310(4) 0.8921(3) 0.0453(11) Uani 1 1 d . . . . .
O5 O 0.2383(5) 0.4561(4) 1.0536(3) 0.0488(11) Uani 1 1 d . . . . .
C24 C 0.5900(5) 0.4609(5) 0.5943(3) 0.0280(11) Uani 1 1 d . . . . .
H24 H 0.541270 0.388661 0.573399 0.034 Uiso 1 1 calc R U . . .
C28 C 0.8299(5) 0.3892(5) 0.5624(3) 0.0275(11) Uani 1 1 d . . . . .
C29 C 0.7152(5) 0.4827(5) 0.5517(3) 0.0273(11) Uani 1 1 d . . . . .
H29 H 0.759980 0.555610 0.574306 0.033 Uiso 1 1 calc R U . . .
C18 C 0.5177(5) 0.4167(5) 0.7278(3) 0.0282(11) Uani 1 1 d . . . . .
C22 C 0.3900(5) 0.5674(5) 0.6411(3) 0.0325(11) Uani 1 1 d . . . . .
H22 H 0.314691 0.620877 0.632204 0.039 Uiso 1 1 calc R U . . .
C33 C 0.9313(5) 0.4398(5) 0.5089(3) 0.0301(11) Uani 1 1 d . . . . .
H33 H 0.976270 0.509746 0.535705 0.036 Uiso 1 1 calc R U . . .
C1 C 0.2075(6) 0.6381(5) 0.9126(3) 0.0328(12) Uani 1 1 d . . . . .
C15 C 0.3607(5) 0.5325(5) 0.8420(3) 0.0321(12) Uani 1 1 d . . . . .
H15 H 0.413431 0.607313 0.846303 0.038 Uiso 1 1 calc R U . . .
C25 C 0.6410(5) 0.4446(5) 0.6812(3) 0.0290(11) Uani 1 1 d . . . . .
H25 H 0.679571 0.521224 0.700803 0.035 Uiso 1 1 calc R U . . .
C9 C 0.0585(5) 0.5633(5) 1.1268(3) 0.0310(11) Uani 1 1 d . . . . .
C17 C 0.3998(5) 0.5033(5) 0.7048(3) 0.0285(11) Uani 1 1 d . . . . .
C12 C -0.1255(6) 0.5558(7) 1.2327(3) 0.0442(15) Uani 1 1 d . . . . .
H12 H -0.189341 0.553494 1.269410 0.053 Uiso 1 1 calc R U . . .
C3 C -0.1927(5) 0.5708(5) 0.9669(3) 0.0327(12) Uani 1 1 d . . . . .
C23 C 0.4883(5) 0.5624(5) 0.5818(3) 0.0342(12) Uani 1 1 d . . . . .
H23A H 0.541894 0.635767 0.583609 0.041 Uiso 1 1 calc R U . . .
H23B H 0.433287 0.555937 0.529454 0.041 Uiso 1 1 calc R U . . .
C36 C 1.1351(6) 0.4352(5) 0.4331(3) 0.0348(12) Uani 1 1 d . . . . .
H36A H 1.069635 0.474255 0.392388 0.042 Uiso 1 1 calc R U . . .
H36B H 1.186785 0.496341 0.465275 0.042 Uiso 1 1 calc R U . . .
C11 C -0.0860(6) 0.6614(6) 1.2054(4) 0.0411(15) Uani 1 1 d . . . . .
H11 H -0.123229 0.731023 1.223263 0.049 Uiso 1 1 calc R U . . .
C10 C 0.0077(6) 0.6666(5) 1.1522(3) 0.0350(13) Uani 1 1 d . . . . .
H10 H 0.036196 0.739078 1.133764 0.042 Uiso 1 1 calc R U . . .
C2 C 0.0971(6) 0.6221(5) 0.9678(3) 0.0315(12) Uani 1 1 d . . . . .
C16 C 0.2908(6) 0.5152(5) 0.7597(3) 0.0340(13) Uani 1 1 d . . . . .
H16A H 0.229399 0.582242 0.743760 0.041 Uiso 1 1 calc R U . . .
H16B H 0.232202 0.444540 0.756742 0.041 Uiso 1 1 calc R U . . .
C34 C 1.0498(6) 0.3640(5) 0.4848(4) 0.0354(13) Uani 1 1 d . . . . .
H34 H 1.006026 0.297574 0.453291 0.043 Uiso 1 1 calc R U . . .
C37 C 1.2398(6) 0.3642(6) 0.3939(4) 0.0400(14) Uani 1 1 d . . . . .
H37A H 1.309135 0.328463 0.434247 0.048 Uiso 1 1 calc R U . . .
H37B H 1.189598 0.300826 0.363216 0.048 Uiso 1 1 calc R U . . .
C8 C -0.2339(5) 0.4843(6) 1.0152(3) 0.0350(12) Uani 1 1 d . . . . .
H8 H -0.189004 0.410822 1.019472 0.042 Uiso 1 1 calc R U . . .
C21 C 0.4629(6) 0.2926(5) 0.7125(4) 0.0356(13) Uani 1 1 d . . . . .
H21A H 0.444365 0.278807 0.656396 0.053 Uiso 1 1 calc R U . . .
H21B H 0.376472 0.282538 0.734975 0.053 Uiso 1 1 calc R U . . .
H21C H 0.533011 0.237098 0.736253 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5721(5) 0.4313(5) 0.8151(3) 0.0323(12) Uani 1 1 d . . . . .
H19A H 0.636650 0.366570 0.831827 0.039 Uiso 1 1 calc R U . . .
H19B H 0.626319 0.504324 0.822449 0.039 Uiso 1 1 calc R U . . .
C32 C 0.8311(6) 0.4838(6) 0.4373(3) 0.0353(12) Uani 1 1 d . . . . .
H32A H 0.823957 0.425910 0.394894 0.042 Uiso 1 1 calc R U . . .
H32B H 0.865805 0.557592 0.418142 0.042 Uiso 1 1 calc R U . . .
C39 C 1.4227(6) 0.3725(5) 0.3001(3) 0.0328(12) Uani 1 1 d . . . . .
H39 H 1.486247 0.329422 0.340621 0.039 Uiso 1 1 calc R U . . .
C6 C -0.4062(6) 0.6165(6) 1.0495(4) 0.0437(15) Uani 1 1 d . . . . .
H6 H -0.480120 0.632865 1.078390 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4576(6) 0.4341(5) 0.8674(3) 0.0358(12) Uani 1 1 d . . . . .
H20A H 0.405628 0.359865 0.863249 0.043 Uiso 1 1 calc R U . . .
H20B H 0.499656 0.445019 0.922155 0.043 Uiso 1 1 calc R U . . .
C26 C 0.7625(6) 0.3569(6) 0.6968(3) 0.0362(13) Uani 1 1 d . . . . .
H26A H 0.799329 0.357779 0.752811 0.043 Uiso 1 1 calc R U . . .
H26B H 0.726315 0.278014 0.683505 0.043 Uiso 1 1 calc R U . . .
C4 C -0.2572(6) 0.6783(5) 0.9590(4) 0.0374(13) Uani 1 1 d . . . . .
H4 H -0.227938 0.735491 0.925469 0.045 Uiso 1 1 calc R U . . .
C14 C 0.0199(6) 0.4565(5) 1.1534(4) 0.0379(13) Uani 1 1 d . . . . .
H14 H 0.056325 0.386788 1.135200 0.045 Uiso 1 1 calc R U . . .
C30 C 0.7759(6) 0.2701(5) 0.5319(4) 0.0370(13) Uani 1 1 d . . . . .
H30A H 0.698018 0.246301 0.558720 0.056 Uiso 1 1 calc R U . . .
H30B H 0.851206 0.212885 0.541624 0.056 Uiso 1 1 calc R U . . .
H30C H 0.743888 0.275228 0.476061 0.056 Uiso 1 1 calc R U . . .
C38 C 1.3158(6) 0.4388(5) 0.3405(3) 0.0345(12) Uani 1 1 d . . . . .
H38A H 1.364424 0.502595 0.371418 0.041 Uiso 1 1 calc R U . . .
H38B H 1.245753 0.474180 0.300363 0.041 Uiso 1 1 calc R U . . .
C31 C 0.6862(6) 0.5023(5) 0.4643(3) 0.0343(13) Uani 1 1 d . . . . .
H31A H 0.651127 0.581858 0.452163 0.041 Uiso 1 1 calc R U . . .
H31B H 0.616992 0.445766 0.439257 0.041 Uiso 1 1 calc R U . . .
C7 C -0.3422(6) 0.5091(6) 1.0568(4) 0.0405(15) Uani 1 1 d . . . . .
H7 H -0.372446 0.452254 1.090217 0.049 Uiso 1 1 calc R U . . .
C27 C 0.8825(6) 0.3830(6) 0.6501(3) 0.0355(13) Uani 1 1 d . . . . .
H27A H 0.954333 0.321618 0.660100 0.043 Uiso 1 1 calc R U . . .
H27B H 0.926438 0.457849 0.667599 0.043 Uiso 1 1 calc R U . . .
C41 C 1.5117(6) 0.4576(6) 0.2599(4) 0.0401(14) Uani 1 1 d . . . . .
H41A H 1.451612 0.499885 0.219210 0.060 Uiso 1 1 calc R U . . .
H41B H 1.582563 0.414378 0.236741 0.060 Uiso 1 1 calc R U . . .
H41C H 1.557488 0.512714 0.298166 0.060 Uiso 1 1 calc R U . . .
C40 C 1.3541(7) 0.2850(6) 0.2417(4) 0.0448(15) Uani 1 1 d . . . . .
H40A H 1.296954 0.231470 0.267617 0.067 Uiso 1 1 calc R U . . .
H40B H 1.426138 0.241295 0.219927 0.067 Uiso 1 1 calc R U . . .
H40C H 1.294708 0.325755 0.199975 0.067 Uiso 1 1 calc R U . . .
C35 C 1.1444(6) 0.3142(6) 0.5544(4) 0.0454(15) Uani 1 1 d . . . . .
H35A H 1.221321 0.271469 0.536417 0.068 Uiso 1 1 calc R U . . .
H35B H 1.090553 0.261486 0.582883 0.068 Uiso 1 1 calc R U . . .
H35C H 1.182236 0.377522 0.588617 0.068 Uiso 1 1 calc R U . . .
C5 C -0.3644(6) 0.7005(6) 1.0010(4) 0.0443(15) Uani 1 1 d . . . . .
H5 H -0.409951 0.773660 0.996606 0.053 Uiso 1 1 calc R U . . .
C13 C -0.0730(7) 0.4532(6) 1.2071(4) 0.0465(16) Uani 1 1 d . . . . .
H13 H -0.100534 0.380925 1.226264 0.056 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
S2 O6 1.433(5) . ?
S2 O5 1.426(5) . ?
S2 C9 1.763(5) . ?
S2 C2 1.864(6) . ?
S1 O3 1.423(5) . ?
S1 O4 1.424(5) . ?
S1 C3 1.758(5) . ?
S1 C2 1.851(6) . ?
F1 C2 1.371(6) . ?
O2 C1 1.329(7) . ?
O2 C15 1.475(6) . ?
O1 C1 1.185(7) . ?
C24 C29 1.529(7) . ?
C24 C25 1.535(7) . ?
C24 C23 1.525(8) . ?
C28 C29 1.540(7) . ?
C28 C33 1.559(7) . ?
C28 C30 1.536(8) . ?
C28 C27 1.541(8) . ?
C29 C31 1.525(7) . ?
C18 C25 1.568(7) . ?
C18 C17 1.526(7) . ?
C18 C21 1.536(8) . ?
C18 C19 1.546(7) . ?
C22 C17 1.325(7) . ?
C22 C23 1.501(7) . ?
C33 C34 1.547(7) . ?
C33 C32 1.552(8) . ?
C1 C2 1.546(8) . ?
C15 C16 1.508(8) . ?
C15 C20 1.498(8) . ?
C25 C26 1.545(7) . ?
C9 C10 1.385(8) . ?
C9 C14 1.386(8) . ?
C17 C16 1.527(7) . ?
C12 C11 1.380(10) . ?
C12 C13 1.386(10) . ?
C3 C8 1.399(8) . ?
C3 C4 1.386(8) . ?
C36 C34 1.541(8) . ?
C36 C37 1.536(8) . ?
C11 C10 1.386(8) . ?
C34 C35 1.523(9) . ?
C37 C38 1.529(8) . ?
C8 C7 1.385(8) . ?
C19 C20 1.532(7) . ?
C32 C31 1.556(7) . ?
C39 C38 1.535(8) . ?
C39 C41 1.537(8) . ?
C39 C40 1.515(8) . ?
C6 C7 1.382(9) . ?
C6 C5 1.383(10) . ?
C26 C27 1.539(8) . ?
C4 C5 1.376(8) . ?
C14 C13 1.386(9) . ?

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 S2 C9 108.4(3) . . ?
O6 S2 C2 101.8(3) . . ?
O5 S2 O6 120.5(3) . . ?
O5 S2 C9 109.4(3) . . ?
O5 S2 C2 108.4(3) . . ?
C9 S2 C2 107.5(2) . . ?
O3 S1 O4 121.3(3) . . ?
O3 S1 C3 109.3(3) . . ?
O3 S1 C2 102.8(3) . . ?
O4 S1 C3 109.8(3) . . ?
O4 S1 C2 107.1(3) . . ?
C3 S1 C2 105.0(3) . . ?
C1 O2 C15 116.7(4) . . ?
C29 C24 C25 109.4(4) . . ?
C23 C24 C29 110.2(4) . . ?
C23 C24 C25 110.2(4) . . ?
C29 C28 C33 99.8(4) . . ?
C29 C28 C27 106.4(4) . . ?
C30 C28 C29 112.3(4) . . ?
C30 C28 C33 109.9(5) . . ?
C30 C28 C27 110.5(5) . . ?
C27 C28 C33 117.5(4) . . ?
C24 C29 C28 115.7(4) . . ?
C31 C29 C24 117.5(4) . . ?
C31 C29 C28 104.6(4) . . ?
C17 C18 C25 109.0(4) . . ?
C17 C18 C21 109.7(4) . . ?
C17 C18 C19 108.9(4) . . ?
C21 C18 C25 111.7(4) . . ?
C21 C18 C19 109.5(5) . . ?
C19 C18 C25 107.9(4) . . ?
C17 C22 C23 125.3(5) . . ?
C34 C33 C28 120.3(5) . . ?
C34 C33 C32 111.7(4) . . ?
C32 C33 C28 103.2(4) . . ?
O2 C1 C2 109.0(5) . . ?
O1 C1 O2 128.9(5) . . ?
O1 C1 C2 122.0(5) . . ?
O2 C15 C16 109.0(4) . . ?
O2 C15 C20 107.4(4) . . ?
C20 C15 C16 111.0(5) . . ?
C24 C25 C18 111.9(4) . . ?
C24 C25 C26 112.5(4) . . ?
C26 C25 C18 113.1(4) . . ?
C10 C9 S2 118.3(4) . . ?
C10 C9 C14 122.1(5) . . ?
C14 C9 S2 119.4(5) . . ?
C18 C17 C16 116.9(4) . . ?
C22 C17 C18 123.1(5) . . ?
C22 C17 C16 120.0(5) . . ?
C11 C12 C13 120.6(5) . . ?
C8 C3 S1 118.6(4) . . ?
C4 C3 S1 119.1(5) . . ?
C4 C3 C8 122.2(5) . . ?
C22 C23 C24 113.0(5) . . ?
C37 C36 C34 114.7(5) . . ?
C12 C11 C10 120.5(6) . . ?
C9 C10 C11 118.2(6) . . ?
S1 C2 S2 120.6(3) . . ?
F1 C2 S2 104.9(4) . . ?
F1 C2 S1 105.4(4) . . ?
F1 C2 C1 107.9(4) . . ?
C1 C2 S2 109.0(4) . . ?
C1 C2 S1 108.4(4) . . ?
C15 C16 C17 110.5(4) . . ?
C36 C34 C33 109.7(5) . . ?
C35 C34 C33 112.5(5) . . ?
C35 C34 C36 110.7(5) . . ?
C38 C37 C36 112.1(5) . . ?
C7 C8 C3 118.0(6) . . ?
C20 C19 C18 114.4(4) . . ?
C33 C32 C31 106.8(4) . . ?
C38 C39 C41 110.4(5) . . ?
C40 C39 C38 112.2(5) . . ?
C40 C39 C41 109.9(5) . . ?
C7 C6 C5 121.1(5) . . ?
C15 C20 C19 108.5(5) . . ?
C27 C26 C25 113.1(5) . . ?
C5 C4 C3 118.5(6) . . ?
C9 C14 C13 118.8(6) . . ?
C37 C38 C39 114.4(5) . . ?
C29 C31 C32 103.6(4) . . ?
C6 C7 C8 120.0(6) . . ?
C26 C27 C28 111.4(5) . . ?
C4 C5 C6 120.2(6) . . ?
C12 C13 C14 119.8(6) . . ?

_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 1.996
_oxdiff_exptl_absorpt_empirical_full_min 0.456
####################################################################### 
# 
# 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_final_CCDC11
_database_code_depnum_ccdc_archive 'CCDC 2427885'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 F O7 S2'
_chemical_formula_sum            'C22 H17 F O7 S2'
_chemical_formula_weight         476.47
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O6F
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'

_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           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   7.43120(10)
_cell_length_b                   19.0072(4)
_cell_length_c                   14.7451(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.212(2)
_cell_angle_gamma                90
_cell_volume                     2079.42(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12192
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.4650
_cell_measurement_theta_min      3.7690
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.442
_exptl_absorpt_coefficient_mu    2.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15835
_diffrn_reflns_point_group_measured_fraction_full 0.800
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         80.208
_diffrn_reflns_theta_min         3.798
_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 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -92.00   0.50    0.15    --  -49.66 -57.00-180.00   50
  2  ω   -104.00 -79.00   0.50    0.35    --  -90.00 -79.00 -34.00   50
  3  ω   -156.00-125.00   0.50    0.35    --  -90.00 -79.00 -34.00   62
  4  ω   -119.00 -84.00   0.50    0.15    --  -49.66 -57.00 -30.00   70
  5  ω   -117.00 -90.00   0.50    0.15    --  -49.66-125.00 120.00   54
  6  ω   -118.00 -93.00   0.50    0.15    --  -49.66-125.00 150.00   50
  7  ω      5.00  53.00   0.50    0.15    --   49.66 -79.00 -34.00   96
  8  ω     42.00 102.00   0.50    0.35    --  111.50 -77.00-120.00  120
  9  ω     90.00 121.00   0.50    0.35    --  111.50 -79.00 -34.00   62
 10  ω     50.00  77.00   0.50    0.35    --  111.50 -79.00 -34.00   54
 11  ω     45.00  72.00   0.50    0.35    --  111.50 -61.00   0.00   54
 12  ω     41.00  67.00   0.50    0.35    --  111.50 -61.00 150.00   52
 13  ω     41.00  69.00   0.50    0.35    --  111.50 -61.00 120.00   56
 14  ω     42.00  71.00   0.50    0.35    --  111.50 -61.00  60.00   58
 15  ω     41.00  70.00   0.50    0.35    --  111.50 -61.00  30.00   58
 16  ω     45.00  70.00   0.50    0.35    --  111.50 -61.00-120.00   50
 17  ω     41.00  71.00   0.50    0.35    --  111.50 -61.00-180.00   60
 18  ω    142.00 178.00   0.50    0.35    --  111.50  30.00   0.00   72
 19  ω     83.00 121.00   0.50    0.15    --   49.66  57.00-180.00   76
 20  ω    119.00 178.00   0.50    0.35    --  111.50  30.00  30.00  118
 21  ω    102.00 171.00   0.50    0.35    --  111.50  79.00  90.00  138
 22  ω    106.00 174.00   0.50    0.35    --  111.50  30.00 150.00  136
 23  ω     59.00 105.00   0.50    0.35    --  111.50 -95.00 -60.00   92
 24  ω     48.00  96.00   0.50    0.35    --  111.50 -95.00 150.00   96
 25  ω    -69.00  22.00   0.50    0.15    --  -49.66  79.00  90.00  182
 26  ω    -65.00 -40.00   0.50    0.35    --  -90.00  79.00  90.00   50
 27  ω    -49.00 -23.00   0.50    0.35    --  -90.00  45.00 -60.00   52
 28  ω     85.00 111.00   0.50    0.15    --   49.78  57.00 150.00   52
 29  ω   -113.00 -87.00   0.50    0.15    --  -49.78-125.00  90.00   52
 30  ω   -121.00 -95.00   0.50    0.15    --  -49.78 -57.00 -60.00   52
 31  ω    103.00 129.00   0.50    0.40    --  111.50  45.00  60.00   52
 32  ω     47.00  73.00   0.50    0.40    --  111.50-125.00-150.00   52
 33  ω     41.00  66.00   0.50    0.40    --  111.50 -61.00-150.00   50
 34  ω     57.00  83.00   0.50    0.40    --  111.50-125.00  30.00   52
 35  ω     76.00 104.00   0.50    0.40    --  111.50 -77.00-180.00   56
 36  ω     46.00  72.00   0.50    0.40    --  111.50 -77.00-180.00   52
 37  ω    151.00 177.00   0.50    0.40    --  111.50  45.00  60.00   52
 38  ω     68.00  97.00   0.50    0.40    --  111.50 -95.00 120.00   58
 39  ω     50.00  77.00   0.50    0.40    --  111.50 -95.00  30.00   54
 40  ω     41.00  67.00   0.50    0.40    --  111.50 -61.00 -30.00   52
 41  ω     85.00 111.00   0.50    0.40    --  111.50 -79.00 -34.00   52
 42  ω   -119.00 -85.00   0.50    0.15    --  -49.78 -57.00-150.00   68
 43  ω   -119.00 -94.00   0.50    0.15    --  -49.78-125.00 -60.00   50
 44  ω   -119.00 -94.00   0.50    0.15    --  -49.78-125.00-120.00   50
 45  ω    -22.00  16.00   0.50    0.15    --  -49.78  19.00   0.00   76
 46  ω     47.00  88.00   0.50    0.15    --   49.78-125.00-180.00   82
 47  ω    -49.00 -24.00   0.50    0.40    --  -90.00  45.00  30.00   50
 48  ω     54.00  80.00   0.50    0.40    --  111.50-125.00 120.00   52
 49  ω     82.00 107.00   0.50    0.40    --  111.50-102.00-156.96   50
 50  ω    124.00 165.00   0.50    0.40    --  111.50  15.00  90.00   82
 51  ω    144.00 170.00   0.50    0.40    --  111.50  45.00 -60.00   52
 52  ω    116.00 168.00   0.50    0.40    --  111.50  15.00-120.00  104
 53  ω     76.00 104.00   0.50    0.40    --  111.50 -95.00  60.00   56
 54  ω     48.00  74.00   0.50    0.40    --  111.50-125.00 -60.00   52
 55  ω     86.00 111.00   0.50    0.40    --  111.50-125.00 -60.00   50
 56  ω    105.00 135.00   0.50    0.40    --  111.50  45.00 -60.00   60
 57  ω     47.00  74.00   0.50    0.40    --  111.50-102.00-156.96   54
 58  ω     80.00 105.00   0.50    0.40    --  111.50 -95.00  90.00   50
 59  ω     77.00 103.00   0.50    0.40    --  111.50 -95.00 -30.00   52
 60  ω     78.00 103.00   0.50    0.40    --  111.50 -95.00 150.00   50
 61  ω     76.00 105.00   0.50    0.40    --  111.50 -95.00-120.00   58
 62  ω     46.00  95.00   0.50    0.40    --  111.50-125.00  60.00   98
 63  ω    124.00 151.00   0.50    0.40    --  111.50  77.00 150.00   54
 64  ω     71.00  96.00   0.50    0.40    --  111.50 -95.00-180.00   50
 65  ω     41.00  66.00   0.50    0.40    --  111.50 -77.00 -30.00   50
 66  ω     85.00 110.00   0.50    0.40    --  111.50-125.00 120.00   50
 67  ω     41.00  66.00   0.50    0.40    --  111.50 -61.00  90.00   50
;
_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      0.0962885000
_diffrn_orient_matrix_UB_12      -0.0610048000
_diffrn_orient_matrix_UB_13      0.0519031000
_diffrn_orient_matrix_UB_21      0.0521715000
_diffrn_orient_matrix_UB_22      -0.0321880000
_diffrn_orient_matrix_UB_23      -0.0907223000
_diffrn_orient_matrix_UB_31      0.1763094000
_diffrn_orient_matrix_UB_32      0.0426036000
_diffrn_orient_matrix_UB_33      0.0054461000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.576
_reflns_Friedel_fraction_full    0.599
_reflns_Friedel_fraction_max     0.572
_reflns_number_gt                3457
_reflns_number_total             3544
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.040(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.091
_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)+(0.0655P)²+1.5542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_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:
 C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
C1 C 0.6001(5) 0.36503(17) 0.5643(2) 0.0228(7) Uani 1 1 d . . . . .
O2 O 0.4351(5) 0.50362(15) 0.09690(19) 0.0356(7) Uani 1 1 d . . . . .
O3 O 0.5554(5) 0.59133(14) 0.18201(19) 0.0333(6) Uani 1 1 d . . . . .
O4 O 0.5176(5) 0.24518(15) 0.6481(2) 0.0376(7) Uani 1 1 d . . . . .
O5 O 0.3212(4) 0.34921(16) 0.66463(19) 0.0351(7) Uani 1 1 d . . . . .
O6 O 0.8859(4) 0.30724(13) 0.65305(19) 0.0283(6) Uani 1 1 d . . . . .
O7 O 0.9034(4) 0.42853(13) 0.59181(18) 0.0279(6) Uani 1 1 d . . . . .
F1 F 0.5203(3) 0.42999(10) 0.55961(14) 0.0234(4) Uani 1 1 d . . . . .
S1 S 0.42713(11) 0.30520(4) 0.60968(6) 0.0248(2) Uani 1 1 d . . . . .
S2 S 0.80808(10) 0.37510(4) 0.63864(6) 0.0213(2) Uani 1 1 d . . . . .
C2 C 0.6584(5) 0.34023(17) 0.4699(2) 0.0221(7) Uani 1 1 d . . . . .
C3 C 0.6350(5) 0.38976(18) 0.3924(2) 0.0227(7) Uani 1 1 d . . . . .
C4 C 0.5658(5) 0.36191(18) 0.3103(3) 0.0251(7) Uani 1 1 d . . . . .
H4 H 0.543057 0.312864 0.304909 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5303(5) 0.40567(19) 0.2367(2) 0.0257(7) Uani 1 1 d . . . . .
H5 H 0.478861 0.387046 0.181365 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5701(5) 0.47748(19) 0.2438(2) 0.0238(7) Uani 1 1 d . . . . .
C7 C 0.6497(5) 0.50451(18) 0.3240(2) 0.0242(7) Uani 1 1 d . . . . .
H7 H 0.683258 0.552710 0.327241 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6805(5) 0.46139(18) 0.3996(2) 0.0236(7) Uani 1 1 d . . . . .
H8 H 0.731393 0.480036 0.455066 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5139(5) 0.52395(19) 0.1655(2) 0.0259(7) Uani 1 1 d . . . . .
C10 C 0.4959(8) 0.6410(2) 0.1124(3) 0.0435(11) Uani 1 1 d . . . . .
H10A H 0.542299 0.626823 0.054206 0.065 Uiso 1 1 calc R U . . .
H10B H 0.541310 0.688004 0.128740 0.065 Uiso 1 1 calc R U . . .
H10C H 0.363923 0.641894 0.107012 0.065 Uiso 1 1 calc R U . . .
C11 C 0.3028(5) 0.28103(18) 0.5091(3) 0.0248(7) Uani 1 1 d . . . . .
C12 C 0.3453(6) 0.2179(2) 0.4684(3) 0.0352(9) Uani 1 1 d . . . . .
H12 H 0.428219 0.186127 0.497837 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2646(8) 0.2019(3) 0.3837(4) 0.0447(12) Uani 1 1 d . . . . .
H13 H 0.293153 0.159276 0.354119 0.054 Uiso 1 1 calc R U . . .
C14 C 0.1436(7) 0.2479(3) 0.3433(3) 0.0425(11) Uani 1 1 d . . . . .
H14 H 0.091002 0.237350 0.284683 0.051 Uiso 1 1 calc R U . . .
C15 C 0.0957(7) 0.3100(3) 0.3862(3) 0.0395(10) Uani 1 1 d . . . . .
H15 H 0.006969 0.340165 0.358280 0.047 Uiso 1 1 calc R U . . .
C16 C 0.1784(6) 0.3277(2) 0.4701(3) 0.0292(8) Uani 1 1 d . . . . .
H16 H 0.150353 0.370359 0.499703 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7373(5) 0.40965(18) 0.7405(2) 0.0238(7) Uani 1 1 d . . . . .
C18 C 0.6943(6) 0.48103(19) 0.7450(3) 0.0286(8) Uani 1 1 d . . . . .
H18 H 0.696796 0.510462 0.692961 0.034 Uiso 1 1 calc R U . . .
C19 C 0.6476(6) 0.5073(2) 0.8284(3) 0.0356(9) Uani 1 1 d . . . . .
H19 H 0.613677 0.555315 0.833444 0.043 Uiso 1 1 calc R U . . .
C20 C 0.6501(6) 0.4641(3) 0.9046(3) 0.0392(10) Uani 1 1 d . . . . .
H20 H 0.620053 0.483019 0.961460 0.047 Uiso 1 1 calc R U . . .
C21 C 0.6963(7) 0.3936(3) 0.8981(3) 0.0386(10) Uani 1 1 d . . . . .
H21 H 0.699608 0.364704 0.950744 0.046 Uiso 1 1 calc R U . . .
C22 C 0.7370(6) 0.3656(2) 0.8162(3) 0.0291(8) Uani 1 1 d . . . . .
H22 H 0.764543 0.316975 0.810999 0.035 Uiso 1 1 calc R U . . .
O1 O 0.7132(4) 0.28073(13) 0.46375(18) 0.0268(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.370(4) . ?
C1 S1 1.868(4) . ?
C1 S2 1.853(4) . ?
C1 C2 1.554(5) . ?
O2 C9 1.203(5) . ?
O3 C9 1.337(5) . ?
O3 C10 1.446(5) . ?
O4 S1 1.426(3) . ?
O5 S1 1.431(3) . ?
O6 S2 1.425(2) . ?
O7 S2 1.437(3) . ?
S1 C11 1.764(4) . ?
S2 C17 1.747(4) . ?
C2 C3 1.483(5) . ?
C2 O1 1.207(4) . ?
C3 C4 1.393(5) . ?
C3 C8 1.405(5) . ?
C4 C5 1.380(5) . ?
C5 C6 1.399(5) . ?
C6 C7 1.391(5) . ?
C6 C9 1.495(5) . ?
C7 C8 1.392(5) . ?
C11 C12 1.387(5) . ?
C11 C16 1.382(6) . ?
C12 C13 1.387(7) . ?
C13 C14 1.367(8) . ?
C14 C15 1.395(7) . ?
C15 C16 1.391(6) . ?
C17 C18 1.396(5) . ?
C17 C22 1.396(5) . ?
C18 C19 1.390(6) . ?
C19 C20 1.391(7) . ?
C20 C21 1.388(7) . ?
C21 C22 1.370(6) . ?

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
F1 C1 S1 105.2(2) . . ?
F1 C1 S2 106.3(2) . . ?
F1 C1 C2 111.7(3) . . ?
S2 C1 S1 114.77(18) . . ?
C2 C1 S1 111.6(2) . . ?
C2 C1 S2 107.2(3) . . ?
C9 O3 C10 116.0(3) . . ?
O4 S1 C1 108.10(18) . . ?
O4 S1 O5 120.32(19) . . ?
O4 S1 C11 109.82(19) . . ?
O5 S1 C1 104.97(16) . . ?
O5 S1 C11 110.47(19) . . ?
C11 S1 C1 101.31(17) . . ?
O6 S2 C1 108.21(16) . . ?
O6 S2 O7 120.32(18) . . ?
O6 S2 C17 110.56(17) . . ?
O7 S2 C1 101.88(16) . . ?
O7 S2 C17 109.13(16) . . ?
C17 S2 C1 105.43(17) . . ?
C3 C2 C1 118.1(3) . . ?
O1 C2 C1 117.6(3) . . ?
O1 C2 C3 124.2(3) . . ?
C4 C3 C2 116.7(3) . . ?
C4 C3 C8 120.6(3) . . ?
C8 C3 C2 122.6(3) . . ?
C5 C4 C3 119.9(3) . . ?
C4 C5 C6 119.9(3) . . ?
C5 C6 C9 118.0(3) . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 C9 121.7(3) . . ?
C6 C7 C8 120.4(3) . . ?
C7 C8 C3 118.8(3) . . ?
O2 C9 O3 123.9(3) . . ?
O2 C9 C6 124.1(3) . . ?
O3 C9 C6 111.9(3) . . ?
C12 C11 S1 117.9(3) . . ?
C16 C11 S1 119.3(3) . . ?
C16 C11 C12 122.6(4) . . ?
C11 C12 C13 118.8(5) . . ?
C14 C13 C12 119.5(4) . . ?
C13 C14 C15 121.5(4) . . ?
C16 C15 C14 119.7(5) . . ?
C11 C16 C15 117.8(4) . . ?
C18 C17 S2 119.1(3) . . ?
C22 C17 S2 118.4(3) . . ?
C22 C17 C18 122.4(4) . . ?
C19 C18 C17 117.4(4) . . ?
C18 C19 C20 120.7(4) . . ?
C21 C20 C19 120.4(4) . . ?
C22 C21 C20 120.3(4) . . ?
C21 C22 C17 118.8(4) . . ?

_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 2.131
_oxdiff_exptl_absorpt_empirical_full_min 0.426
####################################################################### 
# 
# 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_prakash1067_auto
_database_code_depnum_ccdc_archive 'CCDC 2427881'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-07-28
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 F O5 S2'
_chemical_formula_sum            'C20 H21 F O5 S2'
_chemical_formula_weight         424.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H21 F O5 S2'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5965(5)
_cell_length_b                   8.4659(3)
_cell_length_c                   14.5245(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.799(3)
_cell_angle_gamma                90
_cell_volume                     1911.07(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10874
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.9890
_cell_measurement_theta_min      2.7840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             888
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24242
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.089
_diffrn_reflns_theta_min         2.621
_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 0.999
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  21.00   0.50   39.96    --   -3.45 -89.00  67.00  124
  2  ω    -21.00   4.00   0.50   39.96    --   -3.45  89.00-177.00   50
  3  ω     -6.00  31.00   0.50   39.96    --    4.16 -89.00  67.00   74
  4  ω     -5.00  23.00   0.50   39.96    --   -3.45 -99.00-180.00   56
  5  ω     -4.00  21.00   0.50   39.96    --   -3.45 -99.00 -30.00   50
  6  ω      2.00  27.00   0.50   39.96    --   -3.45 -99.00 120.00   50
  7  ω    -59.00  10.00   0.50   39.96    --   -3.45 -57.00 -30.00  138
  8  ω     -2.00  51.00   0.50   39.96    --    4.16  38.00-120.00  106
  9  ω     -7.00  33.00   0.50   39.96    --    4.16 -99.00 -60.00   80
;
_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      -0.0366282000
_diffrn_orient_matrix_UB_12      -0.0436112000
_diffrn_orient_matrix_UB_13      0.0109302000
_diffrn_orient_matrix_UB_21      -0.0271362000
_diffrn_orient_matrix_UB_22      0.0620204000
_diffrn_orient_matrix_UB_23      -0.0178041000
_diffrn_orient_matrix_UB_31      -0.0023844000
_diffrn_orient_matrix_UB_32      -0.0356331000
_diffrn_orient_matrix_UB_33      -0.0443273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3895
_reflns_number_total             5081
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+1.6185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1176
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C28(H28), C18(H18), C24(H24), C21(H21), C20(H20), C19(H19),
 C27(H27), C25(H25), C26(H26)
;
_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
S9 S 0.33265(3) 0.52071(6) 0.56113(3) 0.01823(12) Uani 1 1 d . . . . .
S11 S 0.28333(3) 0.84500(6) 0.63962(3) 0.01959(12) Uani 1 1 d . . . . .
F15 F 0.29225(7) 0.77266(14) 0.46657(7) 0.0219(2) Uani 1 1 d . . . . .
O14 O 0.41891(9) 0.57258(18) 0.55193(11) 0.0267(3) Uani 1 1 d . . . . .
O10 O 0.31068(10) 0.44356(17) 0.64342(9) 0.0252(3) Uani 1 1 d . . . . .
O13 O 0.28694(10) 0.76077(18) 0.72517(10) 0.0268(3) Uani 1 1 d . . . . .
O16 O 0.13775(9) 0.58470(18) 0.59044(10) 0.0249(3) Uani 1 1 d . . . . .
O12 O 0.21663(9) 0.95887(18) 0.61626(11) 0.0272(3) Uani 1 1 d . . . . .
C23 C 0.29599(12) 0.4049(2) 0.46571(12) 0.0185(4) Uani 1 1 d . . . . .
C8 C 0.26594(12) 0.6993(2) 0.54443(12) 0.0184(4) Uani 1 1 d . . . . .
C17 C 0.38307(12) 0.9352(2) 0.62735(13) 0.0183(4) Uani 1 1 d . . . . .
C7 C 0.16762(12) 0.6654(2) 0.53280(13) 0.0194(4) Uani 1 1 d . . . . .
C22 C 0.38734(13) 1.0607(2) 0.56641(14) 0.0217(4) Uani 1 1 d . . . . .
H22 H 0.338748 1.088751 0.525901 0.026 Uiso 1 1 calc R U . . .
C28 C 0.22488(12) 0.3073(2) 0.47374(14) 0.0210(4) Uani 1 1 d . . . . .
H28 H 0.196508 0.305562 0.529118 0.025 Uiso 1 1 calc R U . . .
C18 C 0.45370(13) 0.8904(2) 0.68691(13) 0.0225(4) Uani 1 1 d . . . . .
H18 H 0.450162 0.802929 0.727359 0.027 Uiso 1 1 calc R U . . .
C24 C 0.33890(13) 0.4105(2) 0.38547(13) 0.0229(4) Uani 1 1 d . . . . .
H24 H 0.387082 0.477889 0.381080 0.028 Uiso 1 1 calc R U . . .
C21 C 0.46379(14) 1.1445(2) 0.56559(14) 0.0240(4) Uani 1 1 d . . . . .
H21 H 0.468068 1.230295 0.524061 0.029 Uiso 1 1 calc R U . . .
C1 C 0.11746(12) 0.7389(2) 0.45054(13) 0.0196(4) Uani 1 1 d . . . . .
H1 H 0.142577 0.845352 0.439754 0.024 Uiso 1 1 calc R U . . .
C20 C 0.53386(13) 1.1025(3) 0.62565(14) 0.0257(4) Uani 1 1 d . . . . .
H20 H 0.585852 1.160943 0.625566 0.031 Uiso 1 1 calc R U . . .
C19 C 0.52905(13) 0.9765(3) 0.68569(14) 0.0260(4) Uani 1 1 d . . . . .
H19 H 0.577698 0.948999 0.726269 0.031 Uiso 1 1 calc R U . . .
C6 C 0.12506(13) 0.6382(3) 0.36336(13) 0.0236(4) Uani 1 1 d . . . . .
H6A H 0.186416 0.626689 0.351801 0.028 Uiso 1 1 calc R U . . .
H6B H 0.101378 0.531445 0.372853 0.028 Uiso 1 1 calc R U . . .
C27 C 0.19649(13) 0.2132(2) 0.39946(14) 0.0253(4) Uani 1 1 d . . . . .
H27 H 0.148104 0.146157 0.403518 0.030 Uiso 1 1 calc R U . . .
C4 C -0.01762(14) 0.7438(3) 0.29684(16) 0.0314(5) Uani 1 1 d . . . . .
H4A H -0.046489 0.801227 0.243526 0.038 Uiso 1 1 calc R U . . .
H4B H -0.046966 0.640922 0.302074 0.038 Uiso 1 1 calc R U . . .
C25 C 0.30912(15) 0.3144(3) 0.31192(14) 0.0278(4) Uani 1 1 d . . . . .
H25 H 0.337357 0.315889 0.256449 0.033 Uiso 1 1 calc R U . . .
C26 C 0.23883(15) 0.2167(3) 0.31870(14) 0.0278(4) Uani 1 1 d . . . . .
H26 H 0.219276 0.151585 0.267963 0.033 Uiso 1 1 calc R U . . .
C5 C 0.07601(14) 0.7159(3) 0.28013(15) 0.0289(5) Uani 1 1 d . . . . .
H5A H 0.103468 0.818020 0.267192 0.035 Uiso 1 1 calc R U . . .
H5B H 0.079025 0.647353 0.225252 0.035 Uiso 1 1 calc R U . . .
C3 C -0.02546(14) 0.8388(3) 0.38435(17) 0.0331(5) Uani 1 1 d . . . . .
H3A H -0.086988 0.849265 0.395399 0.040 Uiso 1 1 calc R U . . .
H3B H -0.002148 0.946210 0.376191 0.040 Uiso 1 1 calc R U . . .
C2 C 0.02289(13) 0.7609(3) 0.46817(15) 0.0283(4) Uani 1 1 d . . . . .
H2A H -0.003253 0.657061 0.479866 0.034 Uiso 1 1 calc R U . . .
H2B H 0.018591 0.827871 0.523481 0.034 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
S9 O14 1.4321(15) . ?
S9 O10 1.4287(15) . ?
S9 C23 1.7540(19) . ?
S9 C8 1.839(2) . ?
S11 O13 1.4296(15) . ?
S11 O12 1.4380(15) . ?
S11 C8 1.8561(19) . ?
S11 C17 1.7555(19) . ?
F15 C8 1.382(2) . ?
O16 C7 1.204(2) . ?
C23 C28 1.395(3) . ?
C23 C24 1.392(3) . ?
C8 C7 1.555(3) . ?
C17 C22 1.388(3) . ?
C17 C18 1.395(3) . ?
C7 C1 1.507(3) . ?
C22 C21 1.388(3) . ?
C28 C27 1.384(3) . ?
C18 C19 1.384(3) . ?
C24 C25 1.391(3) . ?
C21 C20 1.386(3) . ?
C1 C6 1.540(3) . ?
C1 C2 1.529(3) . ?
C20 C19 1.384(3) . ?
C6 C5 1.525(3) . ?
C27 C26 1.394(3) . ?
C4 C5 1.519(3) . ?
C4 C3 1.518(3) . ?
C25 C26 1.383(3) . ?
C3 C2 1.527(3) . ?

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
O14 S9 C23 110.15(9) . . ?
O14 S9 C8 105.14(9) . . ?
O10 S9 O14 120.74(9) . . ?
O10 S9 C23 108.68(9) . . ?
O10 S9 C8 108.26(9) . . ?
C23 S9 C8 102.24(9) . . ?
O13 S11 O12 120.98(9) . . ?
O13 S11 C8 107.97(9) . . ?
O13 S11 C17 109.54(9) . . ?
O12 S11 C8 102.25(9) . . ?
O12 S11 C17 108.30(9) . . ?
C17 S11 C8 106.80(9) . . ?
C28 C23 S9 118.27(14) . . ?
C24 C23 S9 119.64(15) . . ?
C24 C23 C28 122.08(18) . . ?
S9 C8 S11 113.72(10) . . ?
F15 C8 S9 105.90(12) . . ?
F15 C8 S11 106.01(12) . . ?
F15 C8 C7 110.58(14) . . ?
C7 C8 S9 113.86(13) . . ?
C7 C8 S11 106.54(12) . . ?
C22 C17 S11 119.21(14) . . ?
C22 C17 C18 121.73(18) . . ?
C18 C17 S11 118.64(15) . . ?
O16 C7 C8 117.67(17) . . ?
O16 C7 C1 125.47(18) . . ?
C1 C7 C8 116.85(16) . . ?
C17 C22 C21 118.93(18) . . ?
C27 C28 C23 118.71(18) . . ?
C19 C18 C17 118.43(19) . . ?
C25 C24 C23 118.02(19) . . ?
C20 C21 C22 119.72(19) . . ?
C7 C1 C6 110.64(16) . . ?
C7 C1 C2 111.20(16) . . ?
C2 C1 C6 110.30(16) . . ?
C19 C20 C21 120.86(19) . . ?
C20 C19 C18 120.31(19) . . ?
C5 C6 C1 110.18(17) . . ?
C28 C27 C26 120.0(2) . . ?
C3 C4 C5 111.25(18) . . ?
C26 C25 C24 120.69(19) . . ?
C25 C26 C27 120.45(19) . . ?
C4 C5 C6 111.46(18) . . ?
C4 C3 C2 111.71(18) . . ?
C3 C2 C1 109.76(18) . . ?

_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 1.721
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_final_CCDC12
_database_code_depnum_ccdc_archive 'CCDC 2427890'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 F O5 S2'
_chemical_formula_sum            'C21 H17 F O5 S2'
_chemical_formula_weight         432.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H25S2O5F
_chemical_oxdiff_usercomment     colorless
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.6629(4)
_cell_length_b                   8.1038(2)
_cell_length_c                   15.2281(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.668(2)
_cell_angle_gamma                90
_cell_volume                     1885.84(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8343
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7830
_cell_measurement_theta_min      2.8520
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.677
_exptl_absorpt_coefficient_mu    2.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 0 0.0440
-1 2 0 0.0569
-1 0 2 0.0544
1 0 -2 0.0744
1 0 0 0.0126
-1 0 0 0.0272
0 1 -1 0.0694
-1 1 1 0.0665
0 -1 1 0.0471
1 -1 -1 0.0449

_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.04
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
0.9989 -1.9991 -0.0013 -0.2891 0.0693 -0.2571
-0.9989 1.9991 0.0013 0.2891 -0.0693 0.2571
-0.9958 0.0002 2.0016 -0.1213 0.0357 0.1675
0.9958 -0.0002 -2.0016 0.1213 -0.0357 -0.1675
0.9965 0.0004 0.0027 -0.0273 -0.0909 -0.0331
-0.9965 -0.0004 -0.0027 0.0273 0.0909 0.0331
-0.0016 0.9994 -1.0002 0.2052 -0.0525 0.0448
-0.9973 0.9997 1.0015 0.0839 -0.0168 0.2123
0.0016 -0.9994 1.0002 -0.2052 0.0525 -0.0448
0.9973 -0.9997 -1.0015 -0.0839 0.0168 -0.2123

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15134
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.918
_diffrn_reflns_theta_min         2.892
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_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 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  13.00   0.50    0.65    --  -49.78  73.00-146.00  160
  2  ω   -115.00 -32.00   0.50    0.65    --  -49.78 -73.00  83.00  166
  3  ω     41.00  69.00   0.50    0.65    --   49.78  73.00-146.00   56
  4  ω      3.00  52.00   0.50    0.65    --   49.78 -73.00  83.00   98
  5  ω    -87.00 -62.00   0.50    2.50    --  -90.00  73.00-146.00   50
  6  ω   -140.00-114.00   0.50    2.50    --  -90.00 -73.00  83.00   52
  7  ω     93.00 170.00   0.50    2.50    --  111.50  73.00-146.00  154
  8  ω     41.00  70.00   0.50    2.50    --  111.50 -73.00  83.00   58
  9  ω   -118.00 -92.00   0.50    0.65    --  -49.78-125.00 -90.00   52
 10  ω   -119.00 -94.00   0.50    0.65    --  -49.78-125.00-120.00   50
 11  ω    -50.00 -25.00   0.50    2.50    --  -90.00  45.00  30.00   50
 12  ω    -45.00 -19.00   0.50    2.50    --  -90.00  45.00-180.00   52
 13  ω     41.00  66.00   0.50    2.50    --  111.50 -61.00 120.00   50
 14  ω     97.00 177.00   0.50    2.50    --  111.50  61.00 -30.00  160
 15  ω    104.00 172.00   0.50    2.50    --  111.50  45.00 120.00  136
 16  ω     97.00 146.00   0.50    2.50    --  111.50 125.00 150.00   98
 17  ω     41.00  72.00   0.50    2.50    --  111.50 -61.00 150.00   62
 18  ω    153.00 178.00   0.50    2.50    --  111.50 125.00 150.00   50
 19  ω     43.00  87.00   0.50    2.50    --  111.50 -77.00 150.00   88
 20  ω     46.00  71.00   0.50    2.50    --  111.50 -61.00  90.00   50
 21  ω     95.00 146.00   0.50    2.50    --  111.50 125.00 120.00  102
 22  ω    103.00 159.00   0.50    2.50    --  111.50  77.00-180.00  112
 23  ω     45.00  70.00   0.50    2.50    --  111.50 -95.00-150.00   50
 24  ω     41.00  69.00   0.50    2.50    --  111.50 -61.00  30.00   56
 25  ω     43.00  68.00   0.50    2.50    --  111.50 -61.00   0.00   50
 26  ω     71.00  96.00   0.50    2.50    --  111.50 -95.00 120.00   50
 27  ω    103.00 166.00   0.50    2.50    --  111.50  61.00 -60.00  126
;
_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      -0.0272818000
_diffrn_orient_matrix_UB_12      0.1310290000
_diffrn_orient_matrix_UB_13      -0.0742015000
_diffrn_orient_matrix_UB_21      -0.0911249000
_diffrn_orient_matrix_UB_22      -0.0801842000
_diffrn_orient_matrix_UB_23      -0.0274716000
_diffrn_orient_matrix_UB_31      -0.0334403000
_diffrn_orient_matrix_UB_32      0.1118553000
_diffrn_orient_matrix_UB_33      0.0670315000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3568
_reflns_number_total             4025
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.127
_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)+(0.0514P)²+1.8496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1174
_refine_special_details          ?
_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:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C15(H15), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C13(H13), C12(H12)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.26406(13) 0.2934(3) 0.51646(13) 0.0168(4) Uani 1 1 d . . . . .
S2 S 0.33077(3) 0.48349(6) 0.53889(3) 0.01728(15) Uani 1 1 d . . . . .
O2 O 0.21388(10) 0.0277(2) 0.58516(11) 0.0257(4) Uani 1 1 d . . . . .
C2 C 0.16427(13) 0.3300(3) 0.49049(14) 0.0170(4) Uani 1 1 d . . . . .
O3 O 0.28337(11) 0.2424(2) 0.69455(10) 0.0250(4) Uani 1 1 d . . . . .
C3 C 0.10998(13) 0.2601(3) 0.40635(14) 0.0176(4) Uani 1 1 d . . . . .
O4 O 0.30691(10) 0.5690(2) 0.61201(10) 0.0230(3) Uani 1 1 d . . . . .
C4 C 0.02566(13) 0.2009(3) 0.40818(14) 0.0194(4) Uani 1 1 d . . . . .
O5 O 0.41898(10) 0.4309(2) 0.54449(11) 0.0256(4) Uani 1 1 d . . . . .
C5 C -0.02313(14) 0.1297(3) 0.32951(16) 0.0243(5) Uani 1 1 d . . . . .
H5 H -0.079545 0.086500 0.329322 0.029 Uiso 1 1 calc R U . . .
C6 C 0.00898(15) 0.1206(3) 0.25146(15) 0.0258(5) Uani 1 1 d . . . . .
H6 H -0.025129 0.069641 0.199211 0.031 Uiso 1 1 calc R U . . .
C7 C 0.09046(15) 0.1854(3) 0.24937(15) 0.0243(5) Uani 1 1 d . . . . .
H7 H 0.111306 0.183185 0.195309 0.029 Uiso 1 1 calc R U . . .
C8 C 0.14123(14) 0.2536(3) 0.32713(14) 0.0197(4) Uani 1 1 d . . . . .
H8 H 0.197616 0.296217 0.326546 0.024 Uiso 1 1 calc R U . . .
S1 S 0.28092(3) 0.14932(6) 0.61429(3) 0.01786(15) Uani 1 1 d . . . . .
F1 F 0.29478(8) 0.20959(15) 0.45145(8) 0.0192(3) Uani 1 1 d . . . . .
O1 O 0.13605(10) 0.40910(19) 0.54539(10) 0.0216(3) Uani 1 1 d . . . . .
C9 C -0.01409(14) 0.2101(3) 0.48990(15) 0.0240(5) Uani 1 1 d . . . . .
H9A H -0.030159 0.324605 0.499355 0.036 Uiso 1 1 calc R U . . .
H9B H 0.028552 0.171325 0.542917 0.036 Uiso 1 1 calc R U . . .
H9C H -0.066453 0.140464 0.480440 0.036 Uiso 1 1 calc R U . . .
C11 C 0.22107(14) 0.6991(3) 0.43441(14) 0.0206(4) Uani 1 1 d . . . . .
H11 H 0.192072 0.704328 0.482984 0.025 Uiso 1 1 calc R U . . .
C15 C 0.33714(16) 0.5847(3) 0.36897(15) 0.0234(4) Uani 1 1 d . . . . .
H15 H 0.386317 0.514151 0.373240 0.028 Uiso 1 1 calc R U . . .
C14 C 0.30683(17) 0.6799(3) 0.29284(15) 0.0282(5) Uani 1 1 d . . . . .
H14 H 0.335074 0.673304 0.243746 0.034 Uiso 1 1 calc R U . . .
C10 C 0.29323(13) 0.5959(3) 0.43894(14) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.38376(13) 0.0590(3) 0.61864(14) 0.0176(4) Uani 1 1 d . . . . .
C17 C 0.39266(15) -0.0644(3) 0.55831(15) 0.0215(4) Uani 1 1 d . . . . .
H17 H 0.344345 -0.095297 0.511777 0.026 Uiso 1 1 calc R U . . .
C18 C 0.47284(15) -0.1421(3) 0.56661(15) 0.0234(5) Uani 1 1 d . . . . .
H18 H 0.480172 -0.225556 0.525081 0.028 Uiso 1 1 calc R U . . .
C19 C 0.54260(15) -0.0973(3) 0.63608(16) 0.0252(5) Uani 1 1 d . . . . .
H19 H 0.597457 -0.151050 0.641966 0.030 Uiso 1 1 calc R U . . .
C20 C 0.53285(15) 0.0251(3) 0.69679(16) 0.0260(5) Uani 1 1 d . . . . .
H20 H 0.580629 0.053307 0.744542 0.031 Uiso 1 1 calc R U . . .
C21 C 0.45342(14) 0.1064(3) 0.68792(14) 0.0210(4) Uani 1 1 d . . . . .
H21 H 0.446634 0.192476 0.728174 0.025 Uiso 1 1 calc R U . . .
C13 C 0.23589(17) 0.7843(3) 0.28746(16) 0.0285(5) Uani 1 1 d . . . . .
H13 H 0.216704 0.850074 0.235211 0.034 Uiso 1 1 calc R U . . .
C12 C 0.19240(15) 0.7940(3) 0.35783(16) 0.0259(5) Uani 1 1 d . . . . .
H12 H 0.143428 0.865144 0.353418 0.031 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
C1 S2 1.850(2) . ?
C1 C2 1.554(3) . ?
C1 S1 1.866(2) . ?
C1 F1 1.372(2) . ?
S2 O4 1.4292(16) . ?
S2 O5 1.4303(16) . ?
S2 C10 1.760(2) . ?
O2 S1 1.4376(16) . ?
C2 C3 1.486(3) . ?
C2 O1 1.211(3) . ?
O3 S1 1.4295(16) . ?
C3 C4 1.411(3) . ?
C3 C8 1.399(3) . ?
C4 C5 1.397(3) . ?
C4 C9 1.510(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.388(3) . ?
S1 C16 1.757(2) . ?
C11 C10 1.396(3) . ?
C11 C12 1.387(3) . ?
C15 C14 1.386(3) . ?
C15 C10 1.392(3) . ?
C14 C13 1.385(4) . ?
C16 C17 1.385(3) . ?
C16 C21 1.395(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.387(3) . ?
C20 C21 1.388(3) . ?
C13 C12 1.392(3) . ?

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
S2 C1 S1 113.47(11) . . ?
C2 C1 S2 112.59(14) . . ?
C2 C1 S1 106.30(13) . . ?
F1 C1 S2 105.80(12) . . ?
F1 C1 C2 113.77(16) . . ?
F1 C1 S1 104.80(13) . . ?
O4 S2 C1 108.30(9) . . ?
O4 S2 O5 120.82(10) . . ?
O4 S2 C10 109.13(10) . . ?
O5 S2 C1 105.19(10) . . ?
O5 S2 C10 109.93(10) . . ?
C10 S2 C1 101.71(9) . . ?
C3 C2 C1 120.02(17) . . ?
O1 C2 C1 115.08(18) . . ?
O1 C2 C3 124.78(18) . . ?
C4 C3 C2 118.27(18) . . ?
C8 C3 C2 121.05(18) . . ?
C8 C3 C4 120.69(19) . . ?
C3 C4 C9 123.79(19) . . ?
C5 C4 C3 117.51(19) . . ?
C5 C4 C9 118.71(19) . . ?
C6 C5 C4 121.5(2) . . ?
C7 C6 C5 120.4(2) . . ?
C6 C7 C8 119.3(2) . . ?
C7 C8 C3 120.5(2) . . ?
O2 S1 C1 102.53(9) . . ?
O2 S1 C16 109.10(10) . . ?
O3 S1 C1 108.96(9) . . ?
O3 S1 O2 120.42(10) . . ?
O3 S1 C16 109.59(10) . . ?
C16 S1 C1 105.01(9) . . ?
C12 C11 C10 118.9(2) . . ?
C14 C15 C10 117.9(2) . . ?
C13 C14 C15 120.8(2) . . ?
C11 C10 S2 117.79(16) . . ?
C15 C10 S2 120.05(17) . . ?
C15 C10 C11 122.1(2) . . ?
C17 C16 S1 120.03(16) . . ?
C17 C16 C21 121.64(19) . . ?
C21 C16 S1 118.17(16) . . ?
C16 C17 C18 119.2(2) . . ?
C17 C18 C19 119.7(2) . . ?
C20 C19 C18 120.7(2) . . ?
C19 C20 C21 120.1(2) . . ?
C20 C21 C16 118.6(2) . . ?
C14 C13 C12 120.7(2) . . ?
C11 C12 C13 119.5(2) . . ?

_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 1.620
_oxdiff_exptl_absorpt_empirical_full_min 0.520
####################################################################### 
# 
# 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_prakash1066_auto
_database_code_depnum_ccdc_archive 'CCDC 2427888'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 F O5 S2'
_chemical_formula_sum            'C17 H15 F O5 S2'
_chemical_formula_weight         382.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c17 h15 f o5 s2'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2863(3)
_cell_length_b                   10.9184(3)
_cell_length_c                   15.4499(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.818(2)
_cell_angle_gamma                90
_cell_volume                     1709.76(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21710
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.1850
_cell_measurement_theta_min      2.7330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             792
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38109
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.091
_diffrn_reflns_theta_min         2.295
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(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 0.864
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  19.00   0.50    1.46    --    4.16 -60.00  56.28  138
  2  ω    -25.00  26.00   0.50    1.46    --    4.16 -77.00 120.00  102
  3  ω     -7.00  35.00   0.50    1.46    --    4.16 -99.00  30.00   84
  4  ω     -7.00  35.00   0.50    1.46    --    4.16 -99.00-180.00   84
  5  ω     -7.00  28.00   0.50    1.46    --   -3.53 -99.00-120.00   70
  6  ω    -25.00  18.00   0.50    1.46    --   -3.53 -77.00-150.00   86
  7  ω    -25.00  18.00   0.50    1.46    --   -3.53 -77.00 -60.00   86
  8  ω    -25.00  18.00   0.50    1.46    --   -3.53 -77.00  90.00   86
  9  ω    -78.00 -53.00   0.50    1.46    --   -3.53 -19.00   0.00   50
 10  ω    -68.00  62.00   0.50    1.46    --    4.16   0.00-150.00  260
 11  ω    -10.00  60.00   0.50    1.46    --    4.16  57.00-120.00  140
 12  ω    -10.00  60.00   0.50    1.46    --    4.16  57.00  30.00  140
;
_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      -0.0370650000
_diffrn_orient_matrix_UB_12      -0.0548287000
_diffrn_orient_matrix_UB_13      -0.0002658000
_diffrn_orient_matrix_UB_21      -0.0582433000
_diffrn_orient_matrix_UB_22      0.0348448000
_diffrn_orient_matrix_UB_23      -0.0002004000
_diffrn_orient_matrix_UB_31      -0.0114876000
_diffrn_orient_matrix_UB_32      0.0001594000
_diffrn_orient_matrix_UB_33      -0.0465885000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4129
_reflns_number_total             4744
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0034(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.052
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.6524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C2(H2), C4(H4), C22(H22), C18(H18), C3(H3), C20(H20),
 C21(H21), C19(H19)
;
_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
S9 S 0.84039(3) 0.65584(3) 0.36629(2) 0.01936(10) Uani 1 1 d . . . . .
S7 S 0.75224(3) 0.39246(3) 0.30795(2) 0.02043(10) Uani 1 1 d . . . . .
F14 F 0.60752(7) 0.58871(7) 0.29393(5) 0.02251(18) Uani 1 1 d . . . . .
O10 O 0.80451(12) 0.63075(10) 0.45016(7) 0.0288(2) Uani 1 1 d . . . . .
O16 O 0.66784(13) 0.33992(9) 0.23353(7) 0.0309(3) Uani 1 1 d . . . . .
O13 O 0.97348(10) 0.63927(10) 0.35296(7) 0.0288(2) Uani 1 1 d . . . . .
O15 O 0.89058(11) 0.36595(10) 0.32436(7) 0.0309(3) Uani 1 1 d . . . . .
O12 O 0.65844(11) 0.61922(11) 0.13845(7) 0.0312(3) Uani 1 1 d . . . . .
C17 C 0.78589(13) 0.80274(12) 0.33121(9) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.73374(12) 0.55887(12) 0.28559(8) 0.0176(2) Uani 1 1 d . . . . .
C1 C 0.68488(13) 0.36450(12) 0.40251(8) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.75178(13) 0.58014(13) 0.18858(8) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.71662(15) 0.31208(13) 0.55459(9) 0.0247(3) Uani 1 1 d . . . . .
H5 H 0.772721 0.292950 0.608323 0.030 Uiso 1 1 calc R U . . .
C23 C 0.88006(14) 0.54804(14) 0.16575(9) 0.0249(3) Uani 1 1 d . . . . .
H23 H 0.949943 0.518658 0.214380 0.030 Uiso 1 1 calc R U . . .
C6 C 0.77083(14) 0.34155(12) 0.48085(9) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.863699 0.345949 0.483704 0.026 Uiso 1 1 calc R U . . .
C2 C 0.54873(14) 0.36067(13) 0.39636(9) 0.0239(3) Uani 1 1 d . . . . .
H2 H 0.492425 0.374899 0.341854 0.029 Uiso 1 1 calc R U . . .
C4 C 0.58123(15) 0.31050(14) 0.54998(9) 0.0265(3) Uani 1 1 d . . . . .
H4 H 0.545285 0.291959 0.601155 0.032 Uiso 1 1 calc R U . . .
C22 C 0.69482(14) 0.86300(13) 0.37272(10) 0.0255(3) Uani 1 1 d . . . . .
H22 H 0.662328 0.826103 0.420476 0.031 Uiso 1 1 calc R U . . .
C18 C 0.83559(15) 0.85413(14) 0.26115(10) 0.0275(3) Uani 1 1 d . . . . .
H18 H 0.898361 0.811374 0.234041 0.033 Uiso 1 1 calc R U . . .
C3 C 0.49670(15) 0.33559(14) 0.47167(10) 0.0281(3) Uani 1 1 d . . . . .
H3 H 0.403893 0.335566 0.469738 0.034 Uiso 1 1 calc R U . . .
C20 C 0.70052(16) 1.03059(14) 0.27261(12) 0.0364(4) Uani 1 1 d . . . . .
H20 H 0.670768 1.109514 0.252242 0.044 Uiso 1 1 calc R U . . .
C25 C 0.92505(18) 0.61991(16) 0.09198(10) 0.0341(4) Uani 1 1 d . . . . .
H25A H 0.867251 0.686763 0.064532 0.041 Uiso 1 1 calc R U . . .
H25B H 1.020749 0.635568 0.096346 0.041 Uiso 1 1 calc R U . . .
C21 C 0.65232(15) 0.97874(14) 0.34266(11) 0.0334(4) Uani 1 1 d . . . . .
H21 H 0.590372 1.022161 0.370090 0.040 Uiso 1 1 calc R U . . .
C19 C 0.79118(16) 0.96941(15) 0.23185(11) 0.0348(4) Uani 1 1 d . . . . .
H19 H 0.823048 1.006244 0.183834 0.042 Uiso 1 1 calc R U . . .
C24 C 0.87822(18) 0.49255(16) 0.07538(10) 0.0345(4) Uani 1 1 d . . . . .
H24A H 0.944797 0.429026 0.069413 0.041 Uiso 1 1 calc R U . . .
H24B H 0.791303 0.480220 0.037600 0.041 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
S9 O10 1.4331(10) . ?
S9 O13 1.4301(11) . ?
S9 C17 1.7540(13) . ?
S9 C8 1.8473(13) . ?
S7 O16 1.4368(11) . ?
S7 O15 1.4317(11) . ?
S7 C8 1.8533(13) . ?
S7 C1 1.7472(13) . ?
F14 C8 1.3658(14) . ?
O12 C11 1.2042(17) . ?
C17 C22 1.388(2) . ?
C17 C18 1.3916(19) . ?
C8 C11 1.5586(18) . ?
C1 C6 1.3945(18) . ?
C1 C2 1.3880(19) . ?
C11 C23 1.4653(19) . ?
C5 C6 1.3888(19) . ?
C5 C4 1.382(2) . ?
C23 C25 1.5195(19) . ?
C23 C24 1.519(2) . ?
C2 C3 1.388(2) . ?
C4 C3 1.392(2) . ?
C22 C21 1.391(2) . ?
C18 C19 1.388(2) . ?
C20 C21 1.386(3) . ?
C20 C19 1.383(3) . ?
C25 C24 1.480(2) . ?

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
O10 S9 C17 109.64(7) . . ?
O10 S9 C8 106.61(6) . . ?
O13 S9 O10 120.43(7) . . ?
O13 S9 C17 109.55(7) . . ?
O13 S9 C8 107.65(6) . . ?
C17 S9 C8 101.18(6) . . ?
O16 S7 C8 102.32(6) . . ?
O16 S7 C1 109.13(7) . . ?
O15 S7 O16 120.51(7) . . ?
O15 S7 C8 107.37(6) . . ?
O15 S7 C1 109.91(6) . . ?
C1 S7 C8 106.52(6) . . ?
C22 C17 S9 119.74(11) . . ?
C22 C17 C18 122.32(13) . . ?
C18 C17 S9 117.94(11) . . ?
S9 C8 S7 113.94(7) . . ?
F14 C8 S9 105.32(8) . . ?
F14 C8 S7 106.58(8) . . ?
F14 C8 C11 109.04(10) . . ?
C11 C8 S9 114.16(9) . . ?
C11 C8 S7 107.46(9) . . ?
C6 C1 S7 118.30(10) . . ?
C2 C1 S7 119.17(10) . . ?
C2 C1 C6 122.47(12) . . ?
O12 C11 C8 117.30(12) . . ?
O12 C11 C23 125.58(13) . . ?
C23 C11 C8 117.11(11) . . ?
C4 C5 C6 120.17(13) . . ?
C11 C23 C25 117.32(13) . . ?
C11 C23 C24 116.49(13) . . ?
C24 C23 C25 58.28(10) . . ?
C5 C6 C1 118.02(13) . . ?
C1 C2 C3 118.51(13) . . ?
C5 C4 C3 121.13(13) . . ?
C17 C22 C21 118.35(14) . . ?
C19 C18 C17 118.37(15) . . ?
C2 C3 C4 119.63(14) . . ?
C19 C20 C21 121.14(14) . . ?
C24 C25 C23 60.85(10) . . ?
C20 C21 C22 119.86(15) . . ?
C20 C19 C18 119.95(15) . . ?
C25 C24 C23 60.87(10) . . ?

_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 9.503
_oxdiff_exptl_absorpt_empirical_full_min 0.553
####################################################################### 
# 
# 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_prakash1065_auto
_database_code_depnum_ccdc_archive 'CCDC 2427886'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F I O5 S2'
_chemical_formula_sum            'C20 H14 F I O5 S2'
_chemical_formula_weight         544.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H14 I F O5 S2'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.4250(4)
_cell_length_b                   8.06270(13)
_cell_length_c                   15.5592(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.101(3)
_cell_angle_gamma                90
_cell_volume                     1995.40(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27065
_cell_measurement_temperature    100.1(5)
_cell_measurement_theta_max      31.0170
_cell_measurement_theta_min      2.6220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47403
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.105
_diffrn_reflns_theta_min         2.561
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.1(5)
_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 0.867
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  21.00   0.50    5.73    --   -3.53  79.00 -98.00   94
  2  ω    -42.00  19.00   0.50    5.73    --   -3.53 -79.00 137.00  122
  3  ω    -42.00  27.00   0.50    5.73    --    4.16 -79.00 137.00  138
  4  ω     -7.00  28.00   0.50    5.73    --   -3.53 -99.00 -60.00   70
  5  ω     -7.00  28.00   0.50    5.73    --   -3.53 -99.00-180.00   70
  6  ω     -7.00  28.00   0.50    5.73    --   -3.53 -99.00  60.00   70
  7  ω     -7.00  28.00   0.50    5.73    --   -3.53 -99.00   0.00   70
  8  ω    -10.00  60.00   0.50    5.73    --    4.16  57.00 -30.00  140
  9  ω    -25.00  26.00   0.50    5.73    --    4.16 -77.00-120.00  102
 10  ω    -25.00  25.00   0.50    5.73    --   -3.53  77.00   0.00  100
 11  ω    -13.00  45.00   0.50    5.73    --   -3.53  38.00-150.00  116
 12  ω    -25.00  26.00   0.50    5.73    --    4.16 -77.00  30.00  102
 13  ω     -7.00  76.00   0.50    5.73    --    4.16  38.00  90.00  166
;
_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      0.0266138000
_diffrn_orient_matrix_UB_12      -0.0703602000
_diffrn_orient_matrix_UB_13      0.0091979000
_diffrn_orient_matrix_UB_21      -0.0123468000
_diffrn_orient_matrix_UB_22      -0.0247605000
_diffrn_orient_matrix_UB_23      0.0362411000
_diffrn_orient_matrix_UB_31      -0.0335835000
_diffrn_orient_matrix_UB_32      -0.0466458000
_diffrn_orient_matrix_UB_33      -0.0330977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4743
_reflns_number_total             5570
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.027
_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)+(0.0172P)²+3.4012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0571
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C29(H29), C5(H5), C23(H23), C4(H4), C21(H21), C19(H19),
 C28(H28), C22(H22), C26(H26), C25(H25), C27(H27), C20(H20)
;
_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
I17 I 0.00126(2) 0.12053(2) 0.40193(2) 0.02036(5) Uani 1 1 d . . . . .
S9 S 0.33584(3) 0.47570(6) 0.50969(3) 0.01547(9) Uani 1 1 d . . . . .
S11 S 0.29276(3) 0.12973(6) 0.56784(3) 0.01487(9) Uani 1 1 d . . . . .
F15 F 0.30904(7) 0.20253(15) 0.41413(8) 0.0160(2) Uani 1 1 d . . . . .
O16 O 0.14844(8) 0.38564(18) 0.46403(10) 0.0171(3) Uani 1 1 d . . . . .
O13 O 0.23125(9) 0.00456(19) 0.52177(11) 0.0223(3) Uani 1 1 d . . . . .
O14 O 0.30778(9) 0.55743(19) 0.57325(10) 0.0202(3) Uani 1 1 d . . . . .
O12 O 0.29135(9) 0.2200(2) 0.64640(10) 0.0221(3) Uani 1 1 d . . . . .
O10 O 0.42248(9) 0.42988(19) 0.53897(11) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.13238(11) 0.2351(2) 0.32573(13) 0.0138(4) Uani 1 1 d . . . . .
C7 C 0.18034(11) 0.3079(2) 0.42043(13) 0.0135(3) Uani 1 1 d . . . . .
C6 C 0.16194(12) 0.2494(2) 0.25449(14) 0.0164(4) Uani 1 1 d . . . . .
H6 H 0.214796 0.300412 0.268223 0.020 Uiso 1 1 calc R U . . .
C18 C 0.39362(12) 0.0478(2) 0.59716(13) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.05405(12) 0.1593(2) 0.30365(14) 0.0157(4) Uani 1 1 d . . . . .
C3 C 0.00787(13) 0.0986(3) 0.21353(15) 0.0199(4) Uani 1 1 d . . . . .
H3 H -0.044782 0.046239 0.199215 0.024 Uiso 1 1 calc R U . . .
C29 C 0.23074(12) 0.6896(3) 0.38056(14) 0.0174(4) Uani 1 1 d . . . . .
H29 H 0.201543 0.695894 0.420370 0.021 Uiso 1 1 calc R U . . .
C8 C 0.27628(11) 0.2799(2) 0.47076(13) 0.0138(3) Uani 1 1 d . . . . .
C5 C 0.11515(13) 0.1903(3) 0.16445(14) 0.0198(4) Uani 1 1 d . . . . .
H5 H 0.135502 0.201757 0.116665 0.024 Uiso 1 1 calc R U . . .
C23 C 0.45864(13) 0.0994(3) 0.68071(14) 0.0185(4) Uani 1 1 d . . . . .
H23 H 0.449881 0.184301 0.718102 0.022 Uiso 1 1 calc R U . . .
C24 C 0.30141(12) 0.5880(2) 0.40387(14) 0.0154(4) Uani 1 1 d . . . . .
C4 C 0.03839(14) 0.1142(3) 0.14466(15) 0.0216(4) Uani 1 1 d . . . . .
H4 H 0.006486 0.072386 0.083216 0.026 Uiso 1 1 calc R U . . .
C21 C 0.54903(13) -0.0978(3) 0.65198(15) 0.0211(4) Uani 1 1 d . . . . .
H21 H 0.602730 -0.148305 0.671231 0.025 Uiso 1 1 calc R U . . .
C19 C 0.40547(13) -0.0744(2) 0.54047(15) 0.0181(4) Uani 1 1 d . . . . .
H19 H 0.360375 -0.107700 0.483721 0.022 Uiso 1 1 calc R U . . .
C28 C 0.20426(14) 0.7811(3) 0.29802(15) 0.0236(4) Uani 1 1 d . . . . .
H28 H 0.156458 0.851128 0.280821 0.028 Uiso 1 1 calc R U . . .
C22 C 0.53645(13) 0.0235(3) 0.70774(15) 0.0218(4) Uani 1 1 d . . . . .
H22 H 0.581440 0.055119 0.764990 0.026 Uiso 1 1 calc R U . . .
C26 C 0.31723(16) 0.6687(3) 0.26464(16) 0.0264(5) Uani 1 1 d . . . . .
H26 H 0.345981 0.661851 0.224383 0.032 Uiso 1 1 calc R U . . .
C25 C 0.34570(14) 0.5764(3) 0.34708(16) 0.0215(4) Uani 1 1 d . . . . .
H25 H 0.393898 0.507443 0.364276 0.026 Uiso 1 1 calc R U . . .
C27 C 0.24763(15) 0.7704(3) 0.24022(16) 0.0276(5) Uani 1 1 d . . . . .
H27 H 0.229262 0.833284 0.183736 0.033 Uiso 1 1 calc R U . . .
C20 C 0.48418(14) -0.1466(3) 0.56823(16) 0.0211(4) Uani 1 1 d . . . . .
H20 H 0.493694 -0.229130 0.530105 0.025 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
I17 C2 2.105(2) . ?
S9 O14 1.4304(15) . ?
S9 O10 1.4358(15) . ?
S9 C8 1.850(2) . ?
S9 C24 1.756(2) . ?
S11 O13 1.4331(16) . ?
S11 O12 1.4314(16) . ?
S11 C18 1.7547(19) . ?
S11 C8 1.864(2) . ?
F15 C8 1.379(2) . ?
O16 C7 1.212(2) . ?
C1 C7 1.486(3) . ?
C1 C6 1.405(3) . ?
C1 C2 1.404(3) . ?
C7 C8 1.546(2) . ?
C6 C5 1.386(3) . ?
C18 C23 1.394(3) . ?
C18 C19 1.393(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.383(3) . ?
C29 C24 1.398(3) . ?
C29 C28 1.386(3) . ?
C5 C4 1.387(3) . ?
C23 C22 1.387(3) . ?
C24 C25 1.394(3) . ?
C21 C22 1.383(3) . ?
C21 C20 1.388(3) . ?
C19 C20 1.387(3) . ?
C28 C27 1.394(3) . ?
C26 C25 1.387(3) . ?
C26 C27 1.382(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
O14 S9 O10 120.74(9) . . ?
O14 S9 C8 108.36(9) . . ?
O14 S9 C24 109.16(9) . . ?
O10 S9 C8 105.12(9) . . ?
O10 S9 C24 110.04(10) . . ?
C24 S9 C8 101.65(9) . . ?
O13 S11 C18 109.26(9) . . ?
O13 S11 C8 102.46(9) . . ?
O12 S11 O13 121.01(10) . . ?
O12 S11 C18 109.53(9) . . ?
O12 S11 C8 108.12(9) . . ?
C18 S11 C8 105.17(9) . . ?
C6 C1 C7 120.72(17) . . ?
C2 C1 C7 120.75(17) . . ?
C2 C1 C6 118.41(17) . . ?
O16 C7 C1 123.94(17) . . ?
O16 C7 C8 116.12(17) . . ?
C1 C7 C8 119.89(16) . . ?
C5 C6 C1 121.01(18) . . ?
C23 C18 S11 118.43(15) . . ?
C19 C18 S11 119.58(15) . . ?
C19 C18 C23 121.85(18) . . ?
C1 C2 I17 123.81(14) . . ?
C3 C2 I17 115.83(14) . . ?
C3 C2 C1 120.30(18) . . ?
C4 C3 C2 120.15(19) . . ?
C28 C29 C24 118.5(2) . . ?
S9 C8 S11 114.12(10) . . ?
F15 C8 S9 105.78(12) . . ?
F15 C8 S11 104.90(12) . . ?
F15 C8 C7 112.74(15) . . ?
C7 C8 S9 112.77(13) . . ?
C7 C8 S11 106.39(12) . . ?
C6 C5 C4 119.50(19) . . ?
C22 C23 C18 118.19(19) . . ?
C29 C24 S9 118.23(15) . . ?
C25 C24 S9 119.61(16) . . ?
C25 C24 C29 122.14(19) . . ?
C3 C4 C5 120.62(19) . . ?
C22 C21 C20 120.84(19) . . ?
C20 C19 C18 118.89(19) . . ?
C29 C28 C27 120.1(2) . . ?
C21 C22 C23 120.49(19) . . ?
C27 C26 C25 121.0(2) . . ?
C26 C25 C24 117.9(2) . . ?
C26 C27 C28 120.4(2) . . ?
C19 C20 C21 119.7(2) . . ?

_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.846
####################################################################### 
# 
# 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_final_CCDC13
_database_code_depnum_ccdc_archive 'CCDC 2427884'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F O5 S2'
_chemical_formula_sum            'C23 H19 F O5 S2'
_chemical_formula_weight         458.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O3F
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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2616(2)
_cell_length_b                   10.5243(3)
_cell_length_c                   13.3594(4)
_cell_angle_alpha                71.543(3)
_cell_angle_beta                 72.343(3)
_cell_angle_gamma                76.521(2)
_cell_volume                     1037.77(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10778
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      78.9250
_cell_measurement_theta_min      3.5840
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.455
_exptl_absorpt_coefficient_mu    2.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.1101
-1 0 -1 0.1763
1 2 -1 0.1324
1 -1 2 0.1266
1 1 0 0.1460
0 -1 -1 0.0520
0 1 1 0.0180
-1 -1 1 0.1760

_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.07
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
0.9996 0.0000 0.9996 0.0043 -0.0851 0.1879
-0.9996 -0.0000 -0.9996 -0.0043 0.0851 -0.1879
0.9991 2.0001 -0.9973 -0.0630 0.3591 0.1836
0.9999 -1.0000 1.9980 0.0379 -0.3072 0.1900
0.9994 1.0001 0.0011 -0.0293 0.1370 0.1857
-0.0000 -0.9990 -1.0001 0.1716 -0.0128 -0.0081
0.0000 0.9990 1.0001 -0.1716 0.0128 0.0081
-0.9992 -1.0006 0.9982 -0.0397 -0.2417 -0.1806

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         79.784
_diffrn_reflns_theta_min         3.601
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(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    103.00 139.00   0.50    0.10    --  111.50  45.00 -30.00   72
  2  ω    122.00 175.00   0.50    0.10    --  111.50  45.00 -60.00  106
  3  ω    150.00 175.00   0.50    0.10    --  111.50  45.00 -30.00   50
  4  ω    140.00 165.00   0.50    0.10    --  111.50  77.00  30.00   50
  5  ω    101.00 135.00   0.50    0.10    --  111.50  77.00  30.00   68
  6  ω    142.00 170.00   0.50    0.10    --  111.50  30.00  90.00   56
  7  ω    106.00 131.00   0.50    0.10    --  111.50  30.00  30.00   50
  8  ω    110.00 135.00   0.50    0.10    --  111.50  30.00  90.00   50
  9  ω    136.00 169.00   0.50    0.10    --  111.50  30.00  30.00   66
 10  ω    106.00 176.00   0.50    0.10    --  111.50  15.00 150.00  140
 11  ω    141.00 170.00   0.50    0.10    --  111.50  45.00-120.00   58
 12  ω    102.00 134.00   0.50    0.10    --  111.50  45.00-120.00   64
 13  ω    107.00 166.00   0.50    0.10    --  111.50  45.00-180.00  118
 14  ω    110.00 136.00   0.50    0.10    --  111.50 141.00 -94.00   52
 15  ω    103.00 147.00   0.50    0.10    --  111.50 129.00  92.00   88
 16  ω     46.00 104.00   0.50    0.10    --  111.50 -77.00-180.00  116
 17  ω     42.00  69.00   0.50    0.10    --  111.50 -61.00-180.00   54
 18  ω     80.00 106.00   0.50    0.10    --  111.50 -77.00-150.00   52
 19  ω     41.00  71.00   0.50    0.10    --  111.50 -61.00-120.00   60
 20  ω     41.00  72.00   0.50    0.10    --  111.50 -61.00 -30.00   62
 21  ω     47.00  72.00   0.50    0.10    --  111.50 -61.00   0.00   50
 22  ω     45.00  70.00   0.50    0.10    --  111.50 -61.00  30.00   50
 23  ω     43.00  68.00   0.50    0.10    --  111.50 -61.00  60.00   50
 24  ω     42.00  68.00   0.50    0.10    --  111.50 -61.00  90.00   52
 25  ω     48.00 106.00   0.50    0.10    --  111.50 -77.00 120.00  116
 26  ω     91.00 128.00   0.50    0.10    --  111.50 -87.00  36.00   74
 27  ω     38.00  94.00   0.50    0.05    --   49.53-129.00  20.00  112
 28  ω     56.00  81.00   0.50    0.10    --  111.50-129.00  20.00   50
 29  ω     42.00  81.00   0.50    0.10    --  111.50 -95.00 120.00   78
 30  ω     49.00  77.00   0.50    0.10    --  111.50-125.00 -30.00   56
 31  ω     64.00 105.00   0.50    0.10    --  111.50 -95.00   0.00   82
 32  ω     48.00 106.00   0.50    0.10    --  111.50-103.00 -61.42  116
 33  ω     63.00 105.00   0.50    0.10    --  111.50 -95.00 -30.00   84
 34  ω     63.00 105.00   0.50    0.10    --  111.50 -95.00  30.00   84
 35  ω     68.00 105.00   0.50    0.10    --  111.50 -95.00  60.00   74
 36  ω     66.00 104.00   0.50    0.10    --  111.50 -95.00 -60.00   76
 37  ω     52.00 100.00   0.50    0.05    --   49.53-141.00-152.00   96
 38  ω     64.00  93.00   0.50    0.10    --  111.50 -95.00-150.00   58
 39  ω     84.00 113.00   0.50    0.10    --  111.50-141.00-152.00   58
 40  ω    -25.00  24.00   0.50    0.05    --  -49.53  19.00 120.00   98
 41  ω    -85.00 -56.00   0.50    0.05    --  -49.53 129.00  92.00   58
 42  ω    -79.00 -54.00   0.50    0.10    --  -90.00 129.00  92.00   50
 43  ω    -75.00 -50.00   0.50    0.05    --  -49.53 141.00 -94.00   50
 44  ω    -84.00 -59.00   0.50    0.10    --  -90.00 141.00 -94.00   50
 45  ω    -24.00  17.00   0.50    0.05    --  -49.53  19.00-150.00   82
 46  ω   -121.00 -92.00   0.50    0.05    --  -49.53 -57.00 -30.00   58
 47  ω   -135.00-102.00   0.50    0.10    --  -90.00 -15.00-120.00   66
 48  ω   -121.00 -82.00   0.50    0.05    --  -49.53 -57.00-150.00   78
 49  ω   -117.00 -83.00   0.50    0.05    --  -49.53 -57.00-120.00   68
 50  ω   -116.00 -88.00   0.50    0.05    --  -49.53-125.00-180.00   56
 51  ω   -112.00 -64.00   0.50    0.05    --  -49.53-141.00-152.00   96
 52  ω   -134.00-109.00   0.50    0.10    --  -90.00-141.00-152.00   50
 53  ω   -119.00 -75.00   0.50    0.05    --  -49.53-129.00  20.00   88
 54  ω   -140.00-115.00   0.50    0.10    --  -90.00-129.00  20.00   50
;
_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      0.0734074000
_diffrn_orient_matrix_UB_12      -0.1026246000
_diffrn_orient_matrix_UB_13      -0.0691171000
_diffrn_orient_matrix_UB_21      0.0195428000
_diffrn_orient_matrix_UB_22      0.1176196000
_diffrn_orient_matrix_UB_23      -0.1046491000
_diffrn_orient_matrix_UB_31      0.1828284000
_diffrn_orient_matrix_UB_32      0.0029956000
_diffrn_orient_matrix_UB_33      0.0051182000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4224
_reflns_number_total             4400
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.072
_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)+(0.0465P)²+0.5699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0936
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
S1 S 0.89366(4) 0.27560(3) 0.89063(3) 0.01832(10) Uani 1 1 d . . . . .
F1 F 0.97020(11) 0.06902(8) 0.80925(7) 0.02191(19) Uani 1 1 d . . . . .
O1 O 0.72730(14) 0.14735(11) 0.71327(9) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.93586(18) 0.20676(14) 0.77089(12) 0.0179(3) Uani 1 1 d . . . . .
S2 S 1.13575(4) 0.25789(3) 0.66863(3) 0.01850(10) Uani 1 1 d . . . . .
O2 O 1.02824(14) 0.20425(12) 0.94370(9) 0.0249(2) Uani 1 1 d . . . . .
C2 C 0.78159(18) 0.24177(15) 0.71884(12) 0.0188(3) Uani 1 1 d . . . . .
O3 O 0.86994(14) 0.42045(10) 0.85275(9) 0.0238(2) Uani 1 1 d . . . . .
C3 C 0.71184(18) 0.38462(14) 0.68051(12) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.768569 0.454162 0.688005 0.024 Uiso 1 1 calc R U . . .
O4 O 1.27527(14) 0.17785(12) 0.71362(9) 0.0280(3) Uani 1 1 d . . . . .
C4 C 0.63036(19) 0.42216(17) 0.58498(13) 0.0251(3) Uani 1 1 d . . . . .
H4A H 0.639417 0.513221 0.533683 0.030 Uiso 1 1 calc R U . . .
H4B H 0.636456 0.349808 0.550748 0.030 Uiso 1 1 calc R U . . .
O5 O 1.11283(14) 0.40296(11) 0.64073(9) 0.0239(2) Uani 1 1 d . . . . .
C5 C 0.51451(18) 0.41420(15) 0.69578(12) 0.0216(3) Uani 1 1 d . . . . .
H5 H 0.455933 0.332052 0.728181 0.026 Uiso 1 1 calc R U . . .
C6 C 0.41523(19) 0.53623(15) 0.73157(12) 0.0219(3) Uani 1 1 d . . . . .
C7 C 0.2528(2) 0.52688(17) 0.80270(13) 0.0252(3) Uani 1 1 d . . . . .
H7 H 0.208518 0.443694 0.827106 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1550(2) 0.63841(18) 0.83818(14) 0.0302(4) Uani 1 1 d . . . . .
H8 H 0.043969 0.631136 0.886041 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2181(2) 0.75969(18) 0.80438(15) 0.0321(4) Uani 1 1 d . . . . .
H9 H 0.150667 0.835933 0.828307 0.039 Uiso 1 1 calc R U . . .
C10 C 0.3814(2) 0.76914(17) 0.73500(15) 0.0314(4) Uani 1 1 d . . . . .
H10 H 0.426408 0.851748 0.712617 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4787(2) 0.65890(16) 0.69827(14) 0.0271(3) Uani 1 1 d . . . . .
H11 H 0.589482 0.666816 0.650104 0.032 Uiso 1 1 calc R U . . .
C12 C 0.69675(19) 0.22245(15) 0.96932(11) 0.0197(3) Uani 1 1 d . . . . .
C13 C 0.6946(2) 0.08913(15) 1.03309(12) 0.0229(3) Uani 1 1 d . . . . .
H13 H 0.798034 0.026644 1.034013 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5374(2) 0.05001(17) 1.09517(13) 0.0289(3) Uani 1 1 d . . . . .
H14 H 0.532389 -0.040218 1.139624 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3874(2) 0.1426(2) 1.09244(14) 0.0330(4) Uani 1 1 d . . . . .
H15 H 0.280037 0.114555 1.134129 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3922(2) 0.2754(2) 1.02974(14) 0.0344(4) Uani 1 1 d . . . . .
H16 H 0.288697 0.338033 1.029760 0.041 Uiso 1 1 calc R U . . .
C17 C 1.13466(19) 0.20609(15) 0.55620(12) 0.0209(3) Uani 1 1 d . . . . .
C18 C 0.5478(2) 0.31704(17) 0.96696(13) 0.0261(3) Uani 1 1 d . . . . .
H18 H 0.552600 0.407718 0.923478 0.031 Uiso 1 1 calc R U . . .
C19 C 1.0528(2) 0.29605(16) 0.47824(12) 0.0231(3) Uani 1 1 d . . . . .
H19 H 0.998044 0.383619 0.485991 0.028 Uiso 1 1 calc R U . . .
C20 C 1.0529(2) 0.25536(19) 0.38926(14) 0.0319(4) Uani 1 1 d . . . . .
H20 H 0.997543 0.315105 0.335344 0.038 Uiso 1 1 calc R U . . .
C21 C 1.1336(3) 0.1278(2) 0.37893(15) 0.0382(4) Uani 1 1 d . . . . .
H21 H 1.131255 0.100055 0.318369 0.046 Uiso 1 1 calc R U . . .
C22 C 1.2178(3) 0.03989(19) 0.45546(16) 0.0393(4) Uani 1 1 d . . . . .
H22 H 1.275281 -0.046516 0.446158 0.047 Uiso 1 1 calc R U . . .
C23 C 1.2180(2) 0.07820(17) 0.54593(14) 0.0303(4) Uani 1 1 d . . . . .
H23 H 1.273925 0.018301 0.599523 0.036 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
S1 C1 1.8663(15) . ?
S1 O2 1.4334(11) . ?
S1 O3 1.4321(11) . ?
S1 C12 1.7547(15) . ?
F1 C1 1.3678(15) . ?
O1 C2 1.2120(18) . ?
C1 S2 1.8609(15) . ?
C1 C2 1.5492(19) . ?
S2 O4 1.4306(11) . ?
S2 O5 1.4329(11) . ?
S2 C17 1.7557(15) . ?
C2 C3 1.464(2) . ?
C3 C4 1.522(2) . ?
C3 C5 1.5486(19) . ?
C4 C5 1.488(2) . ?
C5 C6 1.487(2) . ?
C6 C7 1.394(2) . ?
C6 C11 1.397(2) . ?
C7 C8 1.390(2) . ?
C8 C9 1.381(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.386(2) . ?
C12 C13 1.393(2) . ?
C12 C18 1.393(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.389(3) . ?
C15 C16 1.386(3) . ?
C16 C18 1.387(2) . ?
C17 C19 1.394(2) . ?
C17 C23 1.390(2) . ?
C19 C20 1.385(2) . ?
C20 C21 1.381(3) . ?
C21 C22 1.385(3) . ?
C22 C23 1.391(3) . ?

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
O2 S1 C1 105.13(6) . . ?
O2 S1 C12 110.35(7) . . ?
O3 S1 C1 107.88(6) . . ?
O3 S1 O2 120.51(7) . . ?
O3 S1 C12 109.39(7) . . ?
C12 S1 C1 101.83(7) . . ?
F1 C1 S1 105.84(9) . . ?
F1 C1 S2 105.51(9) . . ?
F1 C1 C2 108.61(11) . . ?
S2 C1 S1 110.76(7) . . ?
C2 C1 S1 113.74(10) . . ?
C2 C1 S2 111.85(10) . . ?
O4 S2 C1 106.13(7) . . ?
O4 S2 O5 121.01(7) . . ?
O4 S2 C17 109.26(7) . . ?
O5 S2 C1 106.33(6) . . ?
O5 S2 C17 109.13(7) . . ?
C17 S2 C1 103.52(7) . . ?
O1 C2 C1 116.82(13) . . ?
O1 C2 C3 124.81(13) . . ?
C3 C2 C1 118.36(12) . . ?
C2 C3 C4 116.75(13) . . ?
C2 C3 C5 114.89(12) . . ?
C4 C3 C5 57.96(10) . . ?
C5 C4 C3 61.92(10) . . ?
C4 C5 C3 60.12(10) . . ?
C6 C5 C3 119.38(12) . . ?
C6 C5 C4 122.75(14) . . ?
C7 C6 C5 118.42(14) . . ?
C7 C6 C11 118.72(15) . . ?
C11 C6 C5 122.85(14) . . ?
C8 C7 C6 120.47(16) . . ?
C9 C8 C7 120.52(16) . . ?
C8 C9 C10 119.36(16) . . ?
C11 C10 C9 120.45(16) . . ?
C10 C11 C6 120.46(16) . . ?
C13 C12 S1 119.41(11) . . ?
C18 C12 S1 118.21(12) . . ?
C18 C12 C13 122.37(14) . . ?
C14 C13 C12 118.26(15) . . ?
C13 C14 C15 120.06(16) . . ?
C16 C15 C14 120.91(16) . . ?
C15 C16 C18 120.11(16) . . ?
C19 C17 S2 118.79(12) . . ?
C23 C17 S2 119.44(12) . . ?
C23 C17 C19 121.76(14) . . ?
C16 C18 C12 118.28(15) . . ?
C20 C19 C17 118.74(15) . . ?
C21 C20 C19 119.97(16) . . ?
C20 C21 C22 121.06(16) . . ?
C21 C22 C23 119.92(17) . . ?
C17 C23 C22 118.53(16) . . ?

_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 1.597
_oxdiff_exptl_absorpt_empirical_full_min 0.686
####################################################################### 
# 
# 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_final_CCDC14
_database_code_depnum_ccdc_archive 'CCDC 2427883'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 F O6 S2'
_chemical_formula_sum            'C21 H17 F O6 S2'
_chemical_formula_weight         448.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H40S2O6
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.13300(10)
_cell_length_b                   8.62390(10)
_cell_length_c                   15.1497(2)
_cell_angle_alpha                103.6500(10)
_cell_angle_beta                 98.8830(10)
_cell_angle_gamma                104.6620(10)
_cell_volume                     972.67(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15160
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.1890
_cell_measurement_theta_min      3.0680
_shelx_estimated_absorpt_T_max   0.744
_shelx_estimated_absorpt_T_min   0.547
_exptl_absorpt_coefficient_mu    2.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 2 0.1122
1 -1 0 0.0734
1 2 -2 0.0766
-2 2 1 0.1177
1 2 0 0.0734
-1 -1 0 0.0583
0 1 2 0.0824
0 -1 -2 0.0422
0 -1 2 0.0381
0 1 -2 0.0701
1 -2 -1 0.0416
-1 -2 -2 0.0224
1 0 2 0.0854

_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.108
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
-2.0012 0.9981 2.0009 0.1260 0.1041 -0.3952
1.0009 -0.9995 -0.0005 -0.0943 0.0658 0.2025
0.9988 2.0003 -1.9991 0.3334 -0.2852 0.1487
-2.0019 1.9983 1.0013 0.2486 -0.0426 -0.4111
0.9987 1.9988 0.0013 0.4532 -0.1072 0.1366
-0.9995 -0.9993 -0.0007 -0.2707 0.0495 -0.1586
-0.0008 0.9979 2.0011 0.3023 0.1203 -0.0340
0.0008 -0.9979 -2.0011 -0.3023 -0.1203 0.0340
0.0007 -1.0009 1.9998 -0.0627 0.2356 0.0099
-0.0007 1.0009 -1.9998 0.0627 -0.2356 -0.0099
1.0017 -1.9982 -1.0014 -0.3368 0.0344 0.2306
-0.9987 -1.9973 -2.0018 -0.5730 -0.0708 -0.1246
1.0001 -0.0016 2.0005 0.2080 0.1861 0.1685

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20652
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         80.075
_diffrn_reflns_theta_min         3.083
_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 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00 106.00   0.50    0.10    --   49.66-143.00-151.00  124
  2  ω     44.00 125.00   0.50    0.25    --  111.50-143.00-151.00  162
  3  ω     42.00 113.00   0.50    0.25    --  111.50-127.00  18.00  142
  4  ω     43.00 111.00   0.50    0.25    --  111.50-125.00 150.00  136
  5  ω     43.00 111.00   0.50    0.25    --  111.50-125.00 150.00  136
  6  ω     50.00 109.00   0.50    0.25    --  111.50-125.00 120.00  118
  7  ω     36.00  95.00   0.50    0.10    --   49.66-127.00  18.00  118
  8  ω     41.00 105.00   0.50    0.25    --  111.50 -95.00   0.00  128
  9  ω     50.00  98.00   0.50    0.25    --  111.50-125.00 -30.00   96
 10  ω     42.00  85.00   0.50    0.25    --  111.50 -95.00  60.00   86
 11  ω     41.00  67.00   0.50    0.25    --  111.50 -95.00-150.00   52
 12  ω     72.00 101.00   0.50    0.25    --  111.50 -95.00-150.00   58
 13  ω     56.00  97.00   0.50    0.25    --  111.50 -95.00-180.00   82
 14  ω     46.00 109.00   0.50    0.25    --  111.50-125.00-180.00  126
 15  ω     79.00 105.00   0.50    0.25    --  111.50 -95.00-120.00   52
 16  ω     66.00 103.00   0.50    0.25    --  111.50 -95.00 -30.00   74
 17  ω     77.00 104.00   0.50    0.25    --  111.50 -95.00   0.00   54
 18  ω     43.00  70.00   0.50    0.25    --  111.50 -95.00 -60.00   54
 19  ω     41.00  67.00   0.50    0.25    --  111.50 -61.00-120.00   52
 20  ω     81.00 106.00   0.50    0.25    --  111.50 -77.00-150.00   50
 21  ω     42.00  99.00   0.50    0.25    --  111.50 -77.00 -60.00  114
 22  ω     41.00  72.00   0.50    0.25    --  111.50 -61.00   0.00   62
 23  ω     52.00  90.00   0.50    0.25    --  111.50 -77.00   0.00   76
 24  ω     45.00  70.00   0.50    0.25    --  111.50 -61.00  90.00   50
 25  ω     44.00  70.00   0.50    0.25    --  111.50 -61.00  30.00   52
 26  ω     41.00  72.00   0.50    0.25    --  111.50 -61.00 150.00   62
 27  ω     94.00 178.00   0.50    0.25    --  111.50 127.00  93.00  168
 28  ω     83.00 171.00   0.50    0.25    --  111.50 143.00 -96.00  176
 29  ω     41.00  72.00   0.50    0.25    --  111.50 -77.00-150.00   62
 30  ω     41.00  72.00   0.50    0.25    --  111.50 -61.00-150.00   62
 31  ω     41.00 160.00   0.50    0.25    --  111.50   0.00-180.00  238
 32  ω    119.00 169.00   0.50    0.25    --  111.50  45.00-180.00  100
 33  ω    104.00 178.00   0.50    0.25    --  111.50  30.00 -90.00  148
 34  ω    104.00 174.00   0.50    0.25    --  111.50  30.00 -30.00  140
 35  ω    104.00 178.00   0.50    0.25    --  111.50  15.00  30.00  148
 36  ω    143.00 177.00   0.50    0.25    --  111.50  15.00  30.00   68
 37  ω    143.00 169.00   0.50    0.25    --  111.50  61.00   0.00   52
 38  ω     41.00 160.00   0.50    0.25    --  111.50   0.00-180.00  238
 39  ω    -25.00  24.00   0.50    0.10    --  -49.66  19.00-120.00   98
 40  ω    -25.00  24.00   0.50    0.10    --  -49.66  19.00-150.00   98
 41  ω    -99.00 -22.00   0.50    0.10    --  -49.66 143.00 -96.00  154
 42  ω    -87.00 -14.00   0.50    0.10    --  -49.66 127.00  93.00  146
 43  ω    -87.00 -20.00   0.50    0.25    --  -90.00 127.00  93.00  134
 44  ω    -50.00 -18.00   0.50    0.25    --  -90.00  45.00  60.00   64
 45  ω   -120.00 -82.00   0.50    0.10    --  -49.66 -57.00 -60.00   76
 46  ω   -120.00 -82.00   0.50    0.10    --  -49.66 -57.00 -90.00   76
 47  ω   -120.00 -82.00   0.50    0.10    --  -49.66 -57.00 150.00   76
 48  ω   -161.00 -80.00   0.50    0.25    --  -90.00 -47.00  76.15  162
 49  ω   -118.00 -87.00   0.50    0.10    --  -49.66-125.00 -30.00   62
 50  ω   -119.00 -72.00   0.50    0.10    --  -49.66-127.00  18.00   94
 51  ω   -118.00 -87.00   0.50    0.10    --  -49.66-125.00-120.00   62
 52  ω   -120.00 -61.00   0.50    0.10    --  -49.66-143.00-151.00  118
 53  ω   -154.00 -61.00   0.50    0.25    --  -90.00-143.00-151.00  186
 54  ω   -160.00 -72.00   0.50    0.25    --  -90.00-127.00  18.00  176
;
_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      0.0881705000
_diffrn_orient_matrix_UB_12      0.1826593000
_diffrn_orient_matrix_UB_13      0.0600343000
_diffrn_orient_matrix_UB_21      0.0081115000
_diffrn_orient_matrix_UB_22      -0.0577352000
_diffrn_orient_matrix_UB_23      0.0889336000
_diffrn_orient_matrix_UB_31      0.1805398000
_diffrn_orient_matrix_UB_32      -0.0218468000
_diffrn_orient_matrix_UB_33      -0.0060484000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3975
_reflns_number_total             4119
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.
;

# start Validation Reply Form
_vrf_PLAT906_final               
;
PROBLEM: Large K Value in the Analysis of Variance ...... 2.026 Check 
RESPONSE: The K value is large only for weak reflections with Fc/Fcmax 
lower than 0.012.
;
# end Validation Reply Form

_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.068
_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)+(0.0402P)²+0.7836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0915
_refine_special_details          ?
_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:
 C16(H16), C4(H4), C20(H20), C10(H10), C5(H5), C14(H14), C13(H13), C7(H7),
 C8(H8), C11(H11), C12(H12), C18(H18), C17(H17), C19(H19)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S1 S 0.39728(5) 0.26422(5) 0.71671(3) 0.02136(11) Uani 1 1 d . . . . .
S2 S 0.05194(5) 0.35402(5) 0.67874(3) 0.02001(11) Uani 1 1 d . . . . .
F1 F 0.35902(12) 0.53837(11) 0.68295(7) 0.0218(2) Uani 1 1 d . . . . .
O5 O -0.03328(15) 0.24969(14) 0.72904(9) 0.0253(3) Uani 1 1 d . . . . .
O4 O 0.03805(16) 0.28967(15) 0.58059(8) 0.0266(3) Uani 1 1 d . . . . .
O1 O 0.27222(16) 0.43366(16) 0.88506(9) 0.0283(3) Uani 1 1 d . . . . .
O2 O 0.56413(16) 0.34211(16) 0.78086(9) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.28151(17) 0.11502(15) 0.72398(9) 0.0292(3) Uani 1 1 d . . . . .
O6 O 0.83797(18) 1.14606(16) 0.99566(9) 0.0328(3) Uani 1 1 d . . . . .
C15 C -0.0007(2) 0.5422(2) 0.70111(11) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.2880(2) 0.4329(2) 0.73272(12) 0.0205(3) Uani 1 1 d . . . . .
C16 C 0.0130(2) 0.6352(2) 0.63708(12) 0.0230(3) Uani 1 1 d . . . . .
H16 H 0.048673 0.596600 0.581219 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7044(2) 1.0033(2) 0.95452(12) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.4543(2) 0.8217(2) 0.83485(12) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.370231 0.802910 0.779374 0.029 Uiso 1 1 calc R U . . .
C3 C 0.4514(2) 0.6920(2) 0.87631(12) 0.0227(3) Uani 1 1 d . . . . .
C20 C -0.0536(2) 0.5948(2) 0.78312(12) 0.0231(3) Uani 1 1 d . . . . .
H20 H -0.062798 0.529350 0.825570 0.028 Uiso 1 1 calc R U . . .
C9 C 0.4264(2) 0.2356(2) 0.60228(12) 0.0217(3) Uani 1 1 d . . . . .
C10 C 0.5633(2) 0.3513(2) 0.58535(12) 0.0233(3) Uani 1 1 d . . . . .
H10 H 0.637731 0.444856 0.634564 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5790(2) 0.9773(2) 0.87407(12) 0.0251(3) Uani 1 1 d . . . . .
H5 H 0.578825 1.065295 0.846349 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3305(2) 0.5202(2) 0.83821(12) 0.0228(3) Uani 1 1 d . . . . .
C14 C 0.3160(2) 0.0971(2) 0.53147(13) 0.0242(3) Uani 1 1 d . . . . .
H14 H 0.222696 0.020216 0.544084 0.029 Uiso 1 1 calc R U . . .
C13 C 0.3452(2) 0.0738(2) 0.44220(13) 0.0270(4) Uani 1 1 d . . . . .
H13 H 0.272795 -0.021189 0.393219 0.032 Uiso 1 1 calc R U . . .
C7 C 0.6974(2) 0.8768(2) 0.99841(12) 0.0261(4) Uani 1 1 d . . . . .
H7 H 0.779611 0.896637 1.054781 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5722(2) 0.7242(2) 0.96022(12) 0.0252(3) Uani 1 1 d . . . . .
H8 H 0.567243 0.639574 0.990937 0.030 Uiso 1 1 calc R U . . .
C11 C 0.5883(2) 0.3270(2) 0.49549(13) 0.0259(4) Uani 1 1 d . . . . .
H11 H 0.679986 0.405120 0.482480 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4798(2) 0.1889(2) 0.42405(13) 0.0274(4) Uani 1 1 d . . . . .
H12 H 0.497856 0.173098 0.362487 0.033 Uiso 1 1 calc R U . . .
C18 C -0.0784(2) 0.8396(2) 0.73888(14) 0.0301(4) Uani 1 1 d . . . . .
H18 H -0.104262 0.942970 0.752159 0.036 Uiso 1 1 calc R U . . .
C17 C -0.0263(2) 0.7845(2) 0.65683(13) 0.0276(4) Uani 1 1 d . . . . .
H17 H -0.017904 0.849727 0.614271 0.033 Uiso 1 1 calc R U . . .
C19 C -0.0929(2) 0.7454(2) 0.80155(13) 0.0288(4) Uani 1 1 d . . . . .
H19 H -0.129620 0.783812 0.857054 0.035 Uiso 1 1 calc R U . . .
C21 C 0.8619(3) 1.2728(2) 0.94798(15) 0.0398(5) Uani 1 1 d . . . . .
H21A H 0.863963 1.222727 0.883139 0.060 Uiso 1 1 calc R U . . .
H21B H 0.972522 1.360490 0.979074 0.060 Uiso 1 1 calc R U . . .
H21C H 0.765423 1.321542 0.949202 0.060 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
S1 O2 1.4354(12) . ?
S1 O3 1.4282(13) . ?
S1 C1 1.8762(17) . ?
S1 C9 1.7541(18) . ?
S2 O5 1.4288(12) . ?
S2 O4 1.4347(13) . ?
S2 C15 1.7520(17) . ?
S2 C1 1.8463(16) . ?
F1 C1 1.3862(18) . ?
O1 C2 1.209(2) . ?
O6 C6 1.355(2) . ?
O6 C21 1.436(2) . ?
C15 C16 1.397(2) . ?
C15 C20 1.390(2) . ?
C1 C2 1.540(2) . ?
C16 C17 1.380(3) . ?
C6 C5 1.395(2) . ?
C6 C7 1.399(2) . ?
C4 C3 1.403(2) . ?
C4 C5 1.390(2) . ?
C3 C2 1.476(2) . ?
C3 C8 1.403(2) . ?
C20 C19 1.390(2) . ?
C9 C10 1.396(2) . ?
C9 C14 1.392(2) . ?
C10 C11 1.382(3) . ?
C14 C13 1.386(3) . ?
C13 C12 1.390(3) . ?
C7 C8 1.373(2) . ?
C11 C12 1.390(3) . ?
C18 C17 1.391(3) . ?
C18 C19 1.388(3) . ?

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
O2 S1 C1 103.56(7) . . ?
O2 S1 C9 109.14(8) . . ?
O3 S1 O2 120.39(8) . . ?
O3 S1 C1 108.83(7) . . ?
O3 S1 C9 109.93(8) . . ?
C9 S1 C1 103.53(7) . . ?
O5 S2 O4 120.50(8) . . ?
O5 S2 C15 109.88(8) . . ?
O5 S2 C1 108.80(7) . . ?
O4 S2 C15 109.73(8) . . ?
O4 S2 C1 105.78(7) . . ?
C15 S2 C1 100.14(7) . . ?
C6 O6 C21 117.44(15) . . ?
C16 C15 S2 119.45(13) . . ?
C20 C15 S2 118.44(13) . . ?
C20 C15 C16 122.11(15) . . ?
S2 C1 S1 112.96(8) . . ?
F1 C1 S1 105.62(10) . . ?
F1 C1 S2 105.08(10) . . ?
F1 C1 C2 112.64(13) . . ?
C2 C1 S1 106.76(11) . . ?
C2 C1 S2 113.60(11) . . ?
C17 C16 C15 118.48(16) . . ?
O6 C6 C5 124.64(16) . . ?
O6 C6 C7 115.32(15) . . ?
C5 C6 C7 120.04(16) . . ?
C5 C4 C3 120.69(16) . . ?
C4 C3 C2 125.09(15) . . ?
C8 C3 C4 118.80(16) . . ?
C8 C3 C2 116.11(15) . . ?
C19 C20 C15 118.44(16) . . ?
C10 C9 S1 118.61(13) . . ?
C14 C9 S1 119.58(13) . . ?
C14 C9 C10 121.79(17) . . ?
C11 C10 C9 118.62(16) . . ?
C4 C5 C6 119.45(16) . . ?
O1 C2 C1 115.41(15) . . ?
O1 C2 C3 124.52(16) . . ?
C3 C2 C1 119.71(14) . . ?
C13 C14 C9 118.62(16) . . ?
C14 C13 C12 120.26(16) . . ?
C8 C7 C6 120.18(16) . . ?
C7 C8 C3 120.67(16) . . ?
C10 C11 C12 120.33(17) . . ?
C13 C12 C11 120.38(17) . . ?
C19 C18 C17 120.75(17) . . ?
C16 C17 C18 120.20(16) . . ?
C18 C19 C20 120.02(17) . . ?

_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.794
####################################################################### 
# 
# 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_final_CCDC15
_database_code_depnum_ccdc_archive 'CCDC 2427882'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F2 O5 S2'
_chemical_formula_sum            'C20 H14 F2 O5 S2'
_chemical_formula_weight         436.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H22S2O5F2
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4575(3)
_cell_length_b                   8.06060(10)
_cell_length_c                   15.0949(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.764(2)
_cell_angle_gamma                90
_cell_volume                     1853.53(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7995
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.1800
_cell_measurement_theta_min      2.8960
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.455
_exptl_absorpt_coefficient_mu    3.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -2 0.1198
-1 0 2 0.1531
-2 -1 0 0.0082
2 1 0 0.0267
1 -1 0 0.0122
-1 1 0 0.0181

_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.03
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
0.9986 0.0001 -1.9999 0.1142 -0.0298 -0.1791
-0.9986 -0.0001 1.9999 -0.1142 0.0298 0.1791
-1.9966 -0.9997 0.0006 -0.2431 -0.1210 -0.0602
1.9966 0.9997 -0.0006 0.2431 0.1210 0.0602
1.0016 -0.9983 0.0004 0.0346 -0.2121 0.0205
-1.0016 0.9983 -0.0004 -0.0346 0.2121 -0.0205

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15232
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         80.015
_diffrn_reflns_theta_min         2.901
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_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 -75.00   0.50    2.00    --  -49.66-130.00-142.00   86
  2  ω    -95.00 -63.00   0.50    2.00    --  -49.66-140.00  43.00   64
  3  ω    -86.00 -36.00   0.50    2.00    --  -49.66 140.00 102.00  100
  4  ω     56.00  82.00   0.50    2.00    --   49.66-140.00  43.00   52
  5  ω   -134.00-109.00   0.50    8.00    --  -90.00-140.00  43.00   50
  6  ω    -81.00 -30.00   0.50    8.00    --  -90.00 130.00 -71.00  102
  7  ω     54.00  79.00   0.50    8.00    --  111.50-130.00-142.00   50
  8  ω     94.00 160.00   0.50    8.00    --  111.50 130.00 -71.00  132
  9  ω     86.00 121.00   0.50    8.00    --  111.50-140.00  43.00   70
 10  ω     56.00  82.00   0.50    8.00    --  111.50-140.00  43.00   52
 11  ω   -117.00 -91.00   0.50    2.00    --  -49.66 -57.00-180.00   52
 12  ω   -118.00 -87.00   0.50    2.00    --  -49.66 -57.00  90.00   62
 13  ω   -120.00 -91.00   0.50    2.00    --  -49.66 -57.00 -60.00   58
 14  ω   -113.00 -88.00   0.50    2.00    --  -49.66 -57.00 -30.00   50
 15  ω   -111.00 -83.00   0.50    2.00    --  -49.66 -57.00-150.00   56
 16  ω     82.00 120.00   0.50    2.00    --   49.66  57.00 -60.00   76
 17  ω     70.00  95.00   0.50    2.00    --   49.66-130.00-142.00   50
 18  ω    -47.00 -21.00   0.50    8.00    --  -90.00  45.00  90.00   52
 19  ω    -50.00 -18.00   0.50    8.00    --  -90.00  45.00 120.00   64
 20  ω     42.00  69.00   0.50    8.00    --  111.50 -61.00  90.00   54
 21  ω     41.00  66.00   0.50    8.00    --  111.50 -61.00   0.00   50
 22  ω     73.00 104.00   0.50    8.00    --  111.50 -95.00 -90.00   62
 23  ω     45.00  72.00   0.50    8.00    --  111.50 -61.00  60.00   54
 24  ω    153.00 178.00   0.50    8.00    --  111.50  30.00  30.00   50
 25  ω    104.00 130.00   0.50    8.00    --  111.50  15.00 -60.00   52
 26  ω     45.00 103.00   0.50    8.00    --  111.50 -95.00-150.00  116
 27  ω    105.00 139.00   0.50    8.00    --  111.50  30.00  30.00   68
 28  ω     64.00  89.00   0.50    8.00    --  111.50 -95.00   0.00   50
 29  ω     44.00  72.00   0.50    8.00    --  111.50 -61.00  30.00   56
 30  ω     65.00 107.00   0.50    8.00    --  111.50-106.00-152.98   84
 31  ω    113.00 176.00   0.50    8.00    --  111.50  30.00 -60.00  126
 32  ω     61.00 102.00   0.50    8.00    --  111.50 -95.00-120.00   82
 33  ω    110.00 164.00   0.50    8.00    --  111.50  30.00-150.00  108
 34  ω     41.00  69.00   0.50    8.00    --  111.50 -77.00-120.00   56
 35  ω     44.00  69.00   0.50    8.00    --  111.50 -77.00  30.00   50
;
_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      0.0926084000
_diffrn_orient_matrix_UB_12      0.0582270000
_diffrn_orient_matrix_UB_13      -0.0108642000
_diffrn_orient_matrix_UB_21      -0.0304692000
_diffrn_orient_matrix_UB_22      0.1819203000
_diffrn_orient_matrix_UB_23      -0.0002964000
_diffrn_orient_matrix_UB_31      0.0269079000
_diffrn_orient_matrix_UB_32      0.0065477000
_diffrn_orient_matrix_UB_33      0.1029738000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3517
_reflns_number_total             3924
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.053
_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)+(0.0650P)²+0.8611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_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
O3 O 0.30217(10) 0.57327(18) 0.62453(9) 0.0262(3) Uani 1 1 d . . . . .
C3 C 0.10715(12) 0.2679(2) 0.42750(12) 0.0210(4) Uani 1 1 d . . . . .
O4 O 0.41471(9) 0.43926(18) 0.54807(10) 0.0270(3) Uani 1 1 d . . . . .
C4 C 0.02442(13) 0.2004(3) 0.42994(13) 0.0263(4) Uani 1 1 d . . . . .
O5 O 0.13067(9) 0.40420(18) 0.56997(9) 0.0258(3) Uani 1 1 d . . . . .
C5 C -0.02819(14) 0.1360(3) 0.35497(15) 0.0328(5) Uani 1 1 d . . . . .
H5 H -0.083540 0.087997 0.358947 0.039 Uiso 1 1 calc R U . . .
C6 C 0.00194(14) 0.1431(3) 0.27351(14) 0.0300(4) Uani 1 1 d . . . . .
H6 H -0.033197 0.099036 0.221049 0.036 Uiso 1 1 calc R U . . .
C7 C 0.08240(13) 0.2135(3) 0.26760(13) 0.0273(4) Uani 1 1 d . . . . .
H7 H 0.101416 0.220118 0.211063 0.033 Uiso 1 1 calc R U . . .
C8 C 0.13509(13) 0.2742(2) 0.34375(12) 0.0234(4) Uani 1 1 d . . . . .
H8 H 0.190728 0.320596 0.339459 0.028 Uiso 1 1 calc R U . . .
C9 C 0.38427(12) 0.0606(2) 0.62383(12) 0.0196(3) Uani 1 1 d . . . . .
C10 C 0.39209(13) -0.0636(2) 0.56201(12) 0.0226(4) Uani 1 1 d . . . . .
H10 H 0.343377 -0.093563 0.517676 0.027 Uiso 1 1 calc R U . . .
C11 C 0.47237(14) -0.1433(2) 0.56605(13) 0.0259(4) Uani 1 1 d . . . . .
H11 H 0.479115 -0.228012 0.524019 0.031 Uiso 1 1 calc R U . . .
C12 C 0.54214(13) -0.0991(3) 0.63117(13) 0.0274(4) Uani 1 1 d . . . . .
H12 H 0.596739 -0.154581 0.633910 0.033 Uiso 1 1 calc R U . . .
C13 C 0.53403(13) 0.0250(3) 0.69274(13) 0.0278(4) Uani 1 1 d . . . . .
H13 H 0.582676 0.053159 0.737585 0.033 Uiso 1 1 calc R U . . .
C14 C 0.45490(13) 0.1082(2) 0.68893(12) 0.0238(4) Uani 1 1 d . . . . .
H14 H 0.449024 0.195523 0.729748 0.029 Uiso 1 1 calc R U . . .
C15 C 0.28545(12) 0.6027(2) 0.45076(11) 0.0197(3) Uani 1 1 d . . . . .
C16 C 0.21207(13) 0.7040(2) 0.45074(12) 0.0228(4) Uani 1 1 d . . . . .
H16 H 0.183137 0.707394 0.501438 0.027 Uiso 1 1 calc R U . . .
C17 C 0.18235(13) 0.7993(3) 0.37536(13) 0.0276(4) Uani 1 1 d . . . . .
H17 H 0.132885 0.869680 0.374196 0.033 Uiso 1 1 calc R U . . .
C18 C 0.22502(15) 0.7918(3) 0.30125(13) 0.0299(4) Uani 1 1 d . . . . .
H18 H 0.204670 0.857938 0.249846 0.036 Uiso 1 1 calc R U . . .
C19 C 0.29697(15) 0.6886(3) 0.30179(12) 0.0285(4) Uani 1 1 d . . . . .
H19 H 0.324748 0.683156 0.250338 0.034 Uiso 1 1 calc R U . . .
C20 C 0.32882(14) 0.5930(2) 0.37716(13) 0.0247(4) Uani 1 1 d . . . . .
H20 H 0.378572 0.523358 0.378355 0.030 Uiso 1 1 calc R U . . .
S1 S 0.28076(3) 0.14948(6) 0.62660(3) 0.02025(13) Uani 1 1 d . . . . .
F1 F 0.28939(7) 0.21565(13) 0.46073(7) 0.0215(2) Uani 1 1 d . . . . .
O1 O 0.21452(9) 0.02568(18) 0.60015(10) 0.0278(3) Uani 1 1 d . . . . .
C1 C 0.26022(12) 0.2973(2) 0.53023(11) 0.0188(3) Uani 1 1 d . . . . .
S2 S 0.32582(3) 0.48922(5) 0.54867(3) 0.01960(13) Uani 1 1 d . . . . .
F2 F -0.00456(8) 0.19121(19) 0.50928(8) 0.0361(3) Uani 1 1 d . . . . .
O2 O 0.28371(10) 0.24055(19) 0.70823(9) 0.0282(3) Uani 1 1 d . . . . .
C2 C 0.16041(12) 0.3315(2) 0.51183(12) 0.0208(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 S2 1.4303(14) . ?
C3 C4 1.396(3) . ?
C3 C8 1.405(3) . ?
C3 C2 1.485(3) . ?
O4 S2 1.4332(14) . ?
C4 C5 1.378(3) . ?
C4 F2 1.350(2) . ?
O5 C2 1.209(2) . ?
C5 C6 1.388(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.381(3) . ?
C9 C10 1.387(3) . ?
C9 C14 1.393(3) . ?
C9 S1 1.7600(19) . ?
C10 C11 1.390(3) . ?
C11 C12 1.377(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.387(3) . ?
C15 C16 1.397(3) . ?
C15 C20 1.394(3) . ?
C15 S2 1.7602(18) . ?
C16 C17 1.385(3) . ?
C17 C18 1.393(3) . ?
C18 C19 1.388(3) . ?
C19 C20 1.393(3) . ?
S1 O1 1.4369(15) . ?
S1 C1 1.8654(18) . ?
S1 O2 1.4283(14) . ?
F1 C1 1.3773(19) . ?
C1 S2 1.8449(19) . ?
C1 C2 1.545(3) . ?

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
C4 C3 C8 117.44(17) . . ?
C4 C3 C2 119.28(16) . . ?
C8 C3 C2 123.28(17) . . ?
C5 C4 C3 122.74(18) . . ?
F2 C4 C3 119.22(17) . . ?
F2 C4 C5 117.99(18) . . ?
C4 C5 C6 118.15(19) . . ?
C7 C6 C5 120.97(19) . . ?
C8 C7 C6 120.09(18) . . ?
C7 C8 C3 120.57(18) . . ?
C10 C9 C14 121.71(17) . . ?
C10 C9 S1 119.52(14) . . ?
C14 C9 S1 118.56(14) . . ?
C9 C10 C11 118.88(18) . . ?
C12 C11 C10 119.81(18) . . ?
C11 C12 C13 121.11(18) . . ?
C12 C13 C14 120.03(18) . . ?
C13 C14 C9 118.43(18) . . ?
C16 C15 S2 118.42(13) . . ?
C20 C15 C16 122.20(17) . . ?
C20 C15 S2 119.36(15) . . ?
C17 C16 C15 118.69(18) . . ?
C16 C17 C18 120.0(2) . . ?
C19 C18 C17 120.63(18) . . ?
C18 C19 C20 120.54(18) . . ?
C19 C20 C15 117.96(19) . . ?
C9 S1 C1 106.05(8) . . ?
O1 S1 C9 108.58(9) . . ?
O1 S1 C1 101.99(8) . . ?
O2 S1 C9 109.48(9) . . ?
O2 S1 O1 120.90(9) . . ?
O2 S1 C1 108.71(8) . . ?
F1 C1 S1 104.74(11) . . ?
F1 C1 S2 105.84(11) . . ?
F1 C1 C2 113.21(14) . . ?
S2 C1 S1 113.67(9) . . ?
C2 C1 S1 106.66(11) . . ?
C2 C1 S2 112.58(13) . . ?
O3 S2 O4 120.91(9) . . ?
O3 S2 C15 108.88(8) . . ?
O3 S2 C1 108.03(8) . . ?
O4 S2 C15 110.15(9) . . ?
O4 S2 C1 105.45(8) . . ?
C15 S2 C1 101.64(8) . . ?
C3 C2 C1 118.94(15) . . ?
O5 C2 C3 124.45(17) . . ?
O5 C2 C1 116.54(16) . . ?

_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 1.481
_oxdiff_exptl_absorpt_empirical_full_min 0.492
####################################################################### 
# 
# 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_final_CCDC16
_database_code_depnum_ccdc_archive 'CCDC 2427875'
loop_
_audit_author_name
_audit_author_address
'Alexander Knieb'
;University of Southern California
United States of America
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2024-06-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C20 H14 Cl F O5 S2'
_chemical_formula_sum            'C20 H14 Cl F O5 S2'
_chemical_formula_weight         452.914
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Cl 0.36457 0.70364 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
S 0.33376 0.55840 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   7.9580(2)
_cell_length_b                   13.8602(3)
_cell_length_c                   8.7664(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.258(2)
_cell_angle_gamma                90
_cell_volume                     965.37(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7452
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2360
_cell_measurement_theta_min      5.0280
_exptl_absorpt_coefficient_mu    4.145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
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    1.558
_exptl_crystal_description       plate
_exptl_crystal_F_000             467.587
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 -1 0.0898
-1 -2 1 0.0943
-1 1 2 0.1033
1 -1 0 0.0439
-1 1 0 0.0027
0 -1 -2 0.1060
-1 -2 0 0.0750
1 2 0 0.0708
0 -2 -1 0.0661
1 1 2 0.1072

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9918
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9390
_diffrn_reflns_point_group_measured_fraction_full 0.8757
_diffrn_reflns_point_group_measured_fraction_max 0.8348
_diffrn_reflns_theta_full        67.5000
_diffrn_reflns_theta_max         79.91
_diffrn_reflns_theta_min         5.05
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9918
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     62.00  88.00   0.50    0.40    --  111.50-125.00 -60.00   52
  2  ω     46.00 102.00   0.50    0.40    --  111.50 -95.00-120.00  112
  3  ω     53.00  99.00   0.50    0.40    --  111.50 -95.00 -60.00   92
  4  ω     46.00  77.00   0.50    0.40    --  111.50 -86.00 148.00   62
  5  ω      0.00  38.00   0.50    0.20    --   49.53 -86.00 148.00   76
  6  ω     77.00 105.00   0.50    0.40    --  111.50 -95.00 -30.00   56
  7  ω     48.00  74.00   0.50    0.40    --  111.50 -95.00 -30.00   52
  8  ω    100.00 126.00   0.50    0.40    --  111.50 -86.00 148.00   52
  9  ω     42.00  70.00   0.50    0.40    --  111.50 -61.00  90.00   56
 10  ω     60.00  85.00   0.50    0.40    --  111.50 -77.00 150.00   50
 11  ω     50.00 101.00   0.50    0.40    --  111.50 -77.00  60.00  102
 12  ω     42.00  78.00   0.50    0.40    --  111.50 -77.00   0.00   72
 13  ω     42.00  68.00   0.50    0.40    --  111.50 -61.00 -90.00   52
 14  ω     44.00  72.00   0.50    0.40    --  111.50 -61.00-120.00   56
 15  ω     43.00  70.00   0.50    0.40    --  111.50 -61.00-180.00   54
 16  ω     50.00 100.00   0.50    0.40    --  111.50 -77.00-180.00  100
 17  ω     43.00  69.00   0.50    0.40    --  111.50 -61.00 -30.00   52
 18  ω     43.00  69.00   0.50    0.40    --  111.50 -61.00   0.00   52
 19  ω     46.00  71.00   0.50    0.40    --  111.50 -61.00 120.00   50
 20  ω    101.00 151.00   0.50    0.40    --  111.50  77.00-120.00  100
 21  ω    130.00 155.00   0.50    0.40    --  111.50  45.00 -60.00   50
 22  ω    119.00 176.00   0.50    0.40    --  111.50  61.00 -30.00  114
 23  ω     84.00 121.00   0.50    0.20    --   49.53  57.00   0.00   74
 24  ω     83.00 116.00   0.50    0.20    --   49.53  57.00 -30.00   66
 25  ω    101.00 175.00   0.50    0.40    --  111.50  61.00 120.00  148
 26  ω    153.00 178.00   0.50    0.40    --  111.50  45.00-120.00   50
 27  ω    103.00 129.00   0.50    0.40    --  111.50  45.00-120.00   52
 28  ω    102.00 144.00   0.50    0.40    --  111.50  86.00 -92.00   84
 29  ω    113.00 160.00   0.50    0.40    --  111.50 125.00-180.00   94
 30  ω    152.00 178.00   0.50    0.40    --  111.50 125.00 150.00   52
 31  ω     95.00 134.00   0.50    0.40    --  111.50 125.00 150.00   78
 32  ω    -74.00  22.00   0.50    0.20    --  -49.53  86.00 -92.00  192
 33  ω    -78.00 -52.00   0.50    0.40    --  -90.00  86.00 -92.00   52
 34  ω    -47.00 -22.00   0.50    0.40    --  -90.00  45.00  90.00   50
 35  ω   -121.00 -82.00   0.50    0.20    --  -49.53 -57.00 150.00   78
 36  ω   -147.00-119.00   0.50    0.40    --  -90.00 -86.00 148.00   56
 37  ω   -117.00 -91.00   0.50    0.20    --  -49.53 -57.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.664
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -17
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                3433
_reflns_number_total             3523
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.2202
_refine_diff_density_min         -0.3940
_refine_diff_density_rms         0.0536
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_d_res_high            0.7830
_refine_ls_d_res_low             8.7522
_refine_ls_goodness_of_fit_ref   1.0352
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.0352
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.7200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0833
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
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_refinement_flags_posn
Cl1 Cl 0.04422(11) 0.11163(5) 0.04444(8) 0.0386(2) Uani 1.000000 .
S1 S 0.51118(7) 0.58502(4) 0.32362(7) 0.01854(14) Uani 1.000000 .
F1 F 0.19626(17) 0.56729(10) 0.24305(15) 0.0192(3) Uani 1.000000 .
O1 O 0.4987(3) 0.68449(13) 0.2799(2) 0.0254(4) Uani 1.000000 .
C1 C 0.2948(3) 0.54984(19) 0.3736(3) 0.0178(5) Uani 1.000000 .
S2 S 0.21230(7) 0.62959(4) 0.52522(7) 0.01870(14) Uani 1.000000 .
O2 O 0.6291(2) 0.55485(16) 0.4433(2) 0.0257(4) Uani 1.000000 .
C2 C 0.2947(3) 0.44459(19) 0.4284(3) 0.0180(5) Uani 1.000000 .
O3 O 0.3520(2) 0.66180(14) 0.6224(2) 0.0247(4) Uani 1.000000 .
C3 C 0.2192(3) 0.36586(18) 0.3317(3) 0.0176(5) Uani 1.000000 .
O4 O 0.0809(2) 0.57333(15) 0.5857(2) 0.0275(4) Uani 1.000000 .
C4 C 0.0870(4) 0.3764(2) 0.2194(3) 0.0260(6) Uani 1.000000 .
H4 H 0.0350(4) 0.4375(2) 0.2030(3) 0.0313(7) Uiso 1.000000 R
O5 O 0.3713(2) 0.42982(14) 0.5494(2) 0.0229(4) Uani 1.000000 .
C5 C 0.0331(4) 0.2978(2) 0.1333(3) 0.0306(6) Uani 1.000000 .
H5 H -0.0566(4) 0.3047(2) 0.0578(3) 0.0367(8) Uiso 1.000000 R
C6 C 0.1095(4) 0.2089(2) 0.1569(3) 0.0263(6) Uani 1.000000 .
C7 C 0.2377(4) 0.1965(2) 0.2686(3) 0.0249(6) Uani 1.000000 .
H7 H 0.2890(4) 0.1352(2) 0.2846(3) 0.0299(7) Uiso 1.000000 R
C8 C 0.2896(3) 0.2746(2) 0.3561(3) 0.0225(5) Uani 1.000000 .
H8 H 0.3753(3) 0.2662(2) 0.4349(3) 0.0270(6) Uiso 1.000000 R
C9 C 0.5319(3) 0.51282(19) 0.1613(3) 0.0193(5) Uani 1.000000 .
C10 C 0.4743(4) 0.5481(2) 0.0194(3) 0.0267(6) Uani 1.000000 .
H10 H 0.4343(4) 0.6125(2) 0.0085(3) 0.0320(7) Uiso 1.000000 R
C11 C 0.4767(4) 0.4872(3) -0.1060(3) 0.0321(7) Uani 1.000000 .
H11 H 0.4404(4) 0.5103(3) -0.2044(3) 0.0386(8) Uiso 1.000000 R
C12 C 0.5314(4) 0.3933(2) -0.0882(4) 0.0336(7) Uani 1.000000 .
H12 H 0.5299(4) 0.3516(2) -0.1743(4) 0.0403(8) Uiso 1.000000 R
C13 C 0.5887(4) 0.3593(2) 0.0541(4) 0.0326(7) Uani 1.000000 .
H13 H 0.6269(4) 0.2945(2) 0.0646(4) 0.0392(8) Uiso 1.000000 R
C14 C 0.5908(4) 0.4187(2) 0.1810(3) 0.0259(6) Uani 1.000000 .
H14 H 0.6311(4) 0.3960(2) 0.2786(3) 0.0311(7) Uiso 1.000000 R
C15 C 0.1222(3) 0.72679(19) 0.4221(3) 0.0197(5) Uani 1.000000 .
C16 C 0.2113(3) 0.8128(2) 0.4101(3) 0.0217(5) Uani 1.000000 .
H16 H 0.3223(3) 0.8191(2) 0.4549(3) 0.0261(6) Uiso 1.000000 R
C17 C 0.1338(4) 0.8889(2) 0.3312(3) 0.0256(6) Uani 1.000000 .
H17 H 0.1906(4) 0.9489(2) 0.3241(3) 0.0307(7) Uiso 1.000000 R
C18 C -0.0271(4) 0.8776(2) 0.2624(3) 0.0244(6) Uani 1.000000 .
H18 H -0.0780(4) 0.9296(2) 0.2062(3) 0.0293(7) Uiso 1.000000 R
C19 C -0.1136(3) 0.7918(2) 0.2750(3) 0.0257(6) Uani 1.000000 .
H19 H -0.2235(3) 0.7852(2) 0.2277(3) 0.0308(7) Uiso 1.000000 R
C20 C -0.0410(3) 0.7154(2) 0.3560(3) 0.0215(5) Uani 1.000000 .
H20 H -0.1005(3) 0.6566(2) 0.3666(3) 0.0258(6) Uiso 1.000000 R


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
Cl1 C6 1.733(3) . ?
S1 O1 1.433(2) . ?
S1 C1 1.865(3) . ?
S1 O2 1.430(2) . ?
S1 C9 1.755(3) . ?
F1 C1 1.372(3) . ?
C1 S2 1.876(3) . ?
C1 C2 1.536(4) . ?
S2 O3 1.4330(19) . ?
S2 O4 1.430(2) . ?
S2 C15 1.753(3) . ?
C2 C3 1.488(4) . ?
C2 O5 1.210(3) . ?
C3 C4 1.407(3) . ?
C3 C8 1.395(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C6 C7 1.384(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 C14 1.394(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(4) . ?
C15 C20 1.401(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(4) . ?
C20 H20 0.9500 . ?

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 S1 O1 105.27(12) . . ?
O2 S1 O1 120.69(13) . . ?
O2 S1 C1 109.09(11) . . ?
C9 S1 O1 109.89(13) . . ?
C9 S1 C1 99.89(12) . . ?
C9 S1 O2 109.90(13) . . ?
F1 C1 S1 104.45(16) . . ?
S2 C1 S1 112.18(13) . . ?
S2 C1 F1 106.29(16) . . ?
C2 C1 S1 109.80(17) . . ?
C2 C1 F1 114.7(2) . . ?
C2 C1 S2 109.37(16) . . ?
O3 S2 C1 108.27(11) . . ?
O4 S2 C1 103.53(12) . . ?
O4 S2 O3 120.58(12) . . ?
C15 S2 C1 103.70(12) . . ?
C15 S2 O3 110.35(12) . . ?
C15 S2 O4 108.91(12) . . ?
C3 C2 C1 121.7(2) . . ?
O5 C2 C1 115.2(2) . . ?
O5 C2 C3 122.8(2) . . ?
C4 C3 C2 125.8(2) . . ?
C8 C3 C2 115.6(2) . . ?
C8 C3 C4 118.6(2) . . ?
H4 C4 C3 120.06(16) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.06(17) . . ?
H5 C5 C4 120.00(17) . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.00(16) . . ?
C5 C6 Cl1 119.5(2) . . ?
C7 C6 Cl1 119.4(2) . . ?
C7 C6 C5 121.1(3) . . ?
H7 C7 C6 120.59(17) . . ?
C8 C7 C6 118.8(3) . . ?
C8 C7 H7 120.59(17) . . ?
C7 C8 C3 121.5(2) . . ?
H8 C8 C3 119.25(15) . . ?
H8 C8 C7 119.25(17) . . ?
C10 C9 S1 118.9(2) . . ?
C14 C9 S1 118.7(2) . . ?
C14 C9 C10 122.1(3) . . ?
H10 C10 C9 120.78(17) . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 H10 120.78(19) . . ?
H11 C11 C10 119.86(19) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.86(18) . . ?
H12 C12 C11 119.72(18) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.72(19) . . ?
H13 C13 C12 119.68(19) . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.68(19) . . ?
C13 C14 C9 118.0(3) . . ?
H14 C14 C9 121.01(16) . . ?
H14 C14 C13 121.01(19) . . ?
C16 C15 S2 120.1(2) . . ?
C20 C15 S2 118.0(2) . . ?
C20 C15 C16 121.9(3) . . ?
H16 C16 C15 120.84(16) . . ?
C17 C16 C15 118.3(3) . . ?
C17 C16 H16 120.84(17) . . ?
H17 C17 C16 119.91(17) . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.91(17) . . ?
H18 C18 C17 119.62(17) . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.62(17) . . ?
H19 C19 C18 119.86(17) . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.86(16) . . ?
C19 C20 C15 118.5(3) . . ?
H20 C20 C15 120.76(16) . . ?
H20 C20 C19 120.76(16) . . ?

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
Cl1 C6 C5 C4 -178.3(2) . . . . ?
Cl1 C6 C7 C8 179.3(2) . . . . ?
S1 C1 C2 C3 -106.55(17) . . . . ?
S1 C1 C2 O5 67.95(19) . . . . ?
S1 C9 C10 C11 -174.0(2) . . . . ?
S1 C9 C14 C13 172.9(2) . . . . ?
F1 C1 C2 C3 10.7(3) . . . . ?
F1 C1 C2 O5 -174.8(2) . . . . ?
C1 C2 C3 C4 -27.7(3) . . . . ?
C1 C2 C3 C8 151.6(2) . . . . ?
S2 C15 C16 C17 -178.2(2) . . . . ?
S2 C15 C20 C19 179.7(2) . . . . ?
C2 C3 C4 C5 177.4(3) . . . . ?
C2 C3 C8 C7 -176.4(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C8 C7 C6 -1.8(3) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
C9 C14 C13 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -1.6(4) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C15 C16 C17 C18 -1.9(3) . . . . ?
C15 C20 C19 C18 -1.1(3) . . . . ?
C16 C17 C18 C19 1.8(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?


_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
;
