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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_1_a
_audit_block_doi                 10.5517/ccdc.csd.cc2fcl7n
_database_code_depnum_ccdc_archive 'CCDC 2245461'
loop_
_audit_author_name
_audit_author_address
'Xiaodong Qiu'
;Nantong University
China
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_audit_creation_date             2022-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29 F3 O4 S'
_chemical_formula_sum            'C29 H29 F3 O4 S'
_chemical_formula_weight         530.58
_chemical_melting_point          ?
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      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                   17.9381(9)
_cell_length_b                   11.1134(7)
_cell_length_c                   26.1609(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5215.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6743
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5085
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1647 before and 0.0868 after correction.
The Ratio of minimum to maximum transmission is 0.6820.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_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  0.1188
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            42615
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         1.927
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3946
_reflns_number_total             6001
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0810
_refine_ls_restrained_S_all      1.120
_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)+(0.0276P)²+10.2468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1656
_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. Restrained distances
 C29-F6
 1.35 with sigma of 0.01
 F2-C29 \\sim F3-C29 \\sim F1-C29
 with sigma of 0.02
 F5-C29 \\sim F4-C29 \\sim F6-C29
 with sigma of 0.02
 F1-F2 \\sim F1-F3 \\sim F2-F3
 with sigma of 0.02
 F4-F5 \\sim F4-F6 \\sim F5-F6
 with sigma of 0.02
 C29-F6 \\sim C29-F4 \\sim C29-F5
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F5) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(F4)=Sof(F5)=Sof(F6)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C7(H7A,H7B), C9(H9A,H9B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,
 H10B), C4(H4A,H4B)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C28(H28), C22(H22), C15(H15), C25(H25), C27(H27), C24(H24),
 C20(H20), C17(H17), C18(H18), C19(H19)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.74413(5) 0.42726(8) 0.26612(3) 0.0305(2) Uani 1 1 d . . . . .
O3 O 0.80501(14) 0.4196(2) 0.30161(9) 0.0428(6) Uani 1 1 d . . . . .
O4 O 0.70534(14) 0.3186(2) 0.25292(10) 0.0425(6) Uani 1 1 d . . . . .
O1 O 0.58414(15) 0.8821(2) 0.51465(11) 0.0525(8) Uani 1 1 d . . . . .
O2 O 0.69823(17) 0.9474(3) 0.49765(12) 0.0649(9) Uani 1 1 d . . . . .
C13 C 0.61669(18) 0.5574(3) 0.25224(12) 0.0282(7) Uani 1 1 d . . . . .
C6 C 0.65514(18) 0.6031(3) 0.38338(12) 0.0278(7) Uani 1 1 d . . . . .
C23 C 0.77975(18) 0.4932(3) 0.20950(12) 0.0278(7) Uani 1 1 d . . . . .
C12 C 0.67920(18) 0.5373(3) 0.29022(12) 0.0266(7) Uani 1 1 d . . . . .
H12 H 0.706356 0.613495 0.293203 0.032 Uiso 1 1 calc R . . . .
C21 C 0.56149(18) 0.6778(3) 0.18448(13) 0.0312(7) Uani 1 1 d . . . . .
C14 C 0.55644(19) 0.4757(3) 0.24840(14) 0.0349(8) Uani 1 1 d . . . . .
H14 H 0.555499 0.407437 0.268934 0.042 Uiso 1 1 calc R . . . .
C11 C 0.6560(2) 0.5000(3) 0.34476(12) 0.0338(8) Uani 1 1 d . . . . .
H11A H 0.606554 0.464677 0.343342 0.041 Uiso 1 1 calc R . . . .
H11B H 0.690015 0.438430 0.356824 0.041 Uiso 1 1 calc R . . . .
C28 C 0.83748(19) 0.5743(3) 0.21390(13) 0.0343(8) Uani 1 1 d . . . . .
H28 H 0.857419 0.592141 0.245829 0.041 Uiso 1 1 calc R . . . .
C3 C 0.65145(19) 0.7727(3) 0.45258(12) 0.0317(8) Uani 1 1 d . . . . .
C2 C 0.6489(2) 0.8756(3) 0.49040(13) 0.0367(8) Uani 1 1 d . . . . .
C22 C 0.61898(19) 0.6547(3) 0.22043(12) 0.0318(8) Uani 1 1 d . . . . .
H22 H 0.659255 0.707188 0.222364 0.038 Uiso 1 1 calc R . . . .
C26 C 0.8350(2) 0.6029(3) 0.12374(13) 0.0381(9) Uani 1 1 d . . . . .
C15 C 0.4994(2) 0.4966(4) 0.21458(14) 0.0387(9) Uani 1 1 d . . . . .
H15 H 0.459763 0.442675 0.212908 0.046 Uiso 1 1 calc R . . . .
C16 C 0.49968(19) 0.5980(3) 0.18240(14) 0.0363(8) Uani 1 1 d . . . . .
C7 C 0.60219(19) 0.7045(3) 0.36711(13) 0.0320(8) Uani 1 1 d . . . . .
H7A H 0.616889 0.734777 0.333830 0.038 Uiso 1 1 calc R . . . .
H7B H 0.551810 0.673404 0.364402 0.038 Uiso 1 1 calc R . . . .
C25 C 0.7771(2) 0.5211(3) 0.11898(13) 0.0387(9) Uani 1 1 d . . . . .
H25 H 0.757241 0.503798 0.086966 0.046 Uiso 1 1 calc R . . . .
C27 C 0.8654(2) 0.6287(3) 0.17075(13) 0.0379(9) Uani 1 1 d . . . . .
H27 H 0.904793 0.682852 0.173349 0.045 Uiso 1 1 calc R . . . .
C24 C 0.7490(2) 0.4655(3) 0.16197(12) 0.0360(8) Uani 1 1 d . . . . .
H24 H 0.710178 0.410438 0.159328 0.043 Uiso 1 1 calc R . . . .
C9 C 0.6280(2) 0.5548(3) 0.43529(12) 0.0361(8) Uani 1 1 d . . . . .
H9A H 0.579982 0.515924 0.430865 0.043 Uiso 1 1 calc R . . . .
H9B H 0.662913 0.494984 0.447755 0.043 Uiso 1 1 calc R . . . .
C5 C 0.73268(18) 0.6564(3) 0.39204(12) 0.0348(8) Uani 1 1 d . . . . .
H5A H 0.767227 0.592645 0.400939 0.042 Uiso 1 1 calc R . . . .
H5B H 0.750074 0.693806 0.360727 0.042 Uiso 1 1 calc R . . . .
C20 C 0.5642(2) 0.7763(3) 0.15055(14) 0.0403(9) Uani 1 1 d . . . . .
H20 H 0.604797 0.828270 0.151316 0.048 Uiso 1 1 calc R . . . .
C8 C 0.6042(2) 0.8065(4) 0.40611(14) 0.0442(10) Uani 1 1 d . . . . .
H8A H 0.553858 0.824760 0.417109 0.053 Uiso 1 1 calc R . . . .
H8B H 0.624770 0.878023 0.390220 0.053 Uiso 1 1 calc R . . . .
C17 C 0.4410(2) 0.6240(4) 0.14781(15) 0.0448(10) Uani 1 1 d . . . . .
H17 H 0.399243 0.574548 0.146965 0.054 Uiso 1 1 calc R . . . .
C18 C 0.4451(2) 0.7202(4) 0.11586(16) 0.0495(11) Uani 1 1 d . . . . .
H18 H 0.406137 0.735901 0.093365 0.059 Uiso 1 1 calc R . . . .
C19 C 0.5077(2) 0.7962(4) 0.11656(15) 0.0483(10) Uani 1 1 d . . . . .
H19 H 0.510662 0.860228 0.093787 0.058 Uiso 1 1 calc R . . . .
C10 C 0.6206(2) 0.6560(3) 0.47484(14) 0.0463(10) Uani 1 1 d . . . . .
H10A H 0.568649 0.666639 0.483956 0.056 Uiso 1 1 calc R . . . .
H10B H 0.648016 0.634868 0.505536 0.056 Uiso 1 1 calc R . . . .
C4 C 0.7311(2) 0.7499(4) 0.43479(15) 0.0505(11) Uani 1 1 d . . . . .
H4A H 0.760766 0.721619 0.463350 0.061 Uiso 1 1 calc R . . . .
H4B H 0.752718 0.824540 0.422606 0.061 Uiso 1 1 calc R . . . .
C29 C 0.8640(3) 0.6649(4) 0.07706(16) 0.0608(13) Uani 1 1 d D . . . .
C1 C 0.5745(3) 0.9825(4) 0.54892(17) 0.0611(13) Uani 1 1 d . . . . .
H1A H 0.587235 1.055726 0.531552 0.092 Uiso 1 1 calc GR . . . .
H1B H 0.606260 0.972436 0.578123 0.092 Uiso 1 1 calc GR . . . .
H1C H 0.523442 0.986112 0.559891 0.092 Uiso 1 1 calc GR . . . .
F1 F 0.9208(3) 0.7377(5) 0.0863(2) 0.0716(18) Uani 0.748(10) 1 d D . P A 1
F2 F 0.8106(2) 0.7470(5) 0.06010(17) 0.086(2) Uani 0.748(10) 1 d D . P A 1
F3 F 0.8764(6) 0.5986(5) 0.0388(2) 0.128(4) Uani 0.748(10) 1 d D . P A 1
F4 F 0.9276(7) 0.5950(14) 0.0623(5) 0.080(5) Uani 0.252(10) 1 d D . P A 2
F5 F 0.8257(7) 0.6628(15) 0.0370(5) 0.077(5) Uani 0.252(10) 1 d D U P A 2
F6 F 0.8942(11) 0.7705(11) 0.0862(9) 0.092(7) Uani 0.252(10) 1 d D U P A 2


_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 O3 1.436(2) . ?
S1 O4 1.436(3) . ?
S1 C23 1.772(3) . ?
S1 C12 1.803(3) . ?
O1 C2 1.326(4) . ?
O1 C1 1.442(4) . ?
O2 C2 1.206(4) . ?
C13 C12 1.515(4) . ?
C13 C14 1.415(4) . ?
C13 C22 1.365(5) . ?
C6 C11 1.528(4) . ?
C6 C7 1.534(5) . ?
C6 C9 1.540(4) . ?
C6 C5 1.529(4) . ?
C23 C28 1.378(5) . ?
C23 C24 1.395(4) . ?
C12 C11 1.543(4) . ?
C21 C22 1.419(5) . ?
C21 C16 1.421(5) . ?
C21 C20 1.410(5) . ?
C14 C15 1.373(5) . ?
C28 C27 1.375(5) . ?
C3 C2 1.513(5) . ?
C3 C8 1.528(5) . ?
C3 C10 1.526(5) . ?
C3 C4 1.523(5) . ?
C26 C25 1.387(5) . ?
C26 C27 1.375(5) . ?
C26 C29 1.496(5) . ?
C15 C16 1.407(5) . ?
C16 C17 1.417(5) . ?
C7 C8 1.525(5) . ?
C25 C24 1.378(5) . ?
C9 C10 1.534(5) . ?
C5 C4 1.526(5) . ?
C20 C19 1.366(5) . ?
C17 C18 1.359(6) . ?
C18 C19 1.404(6) . ?
C29 F1 1.324(6) . ?
C29 F2 1.396(6) . ?
C29 F3 1.263(6) . ?
C29 F4 1.434(12) . ?
C29 F5 1.253(11) . ?
C29 F6 1.315(8) . ?

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 C23 106.90(15) . . ?
O3 S1 C12 107.77(15) . . ?
O4 S1 O3 118.33(16) . . ?
O4 S1 C23 108.76(15) . . ?
O4 S1 C12 109.96(15) . . ?
C23 S1 C12 104.16(15) . . ?
C2 O1 C1 116.4(3) . . ?
C14 C13 C12 121.2(3) . . ?
C22 C13 C12 119.6(3) . . ?
C22 C13 C14 119.2(3) . . ?
C11 C6 C7 111.9(3) . . ?
C11 C6 C9 108.9(3) . . ?
C11 C6 C5 112.3(3) . . ?
C7 C6 C9 107.8(3) . . ?
C5 C6 C7 108.7(3) . . ?
C5 C6 C9 107.0(3) . . ?
C28 C23 S1 118.2(2) . . ?
C28 C23 C24 121.1(3) . . ?
C24 C23 S1 120.8(3) . . ?
C13 C12 S1 110.4(2) . . ?
C13 C12 C11 116.5(3) . . ?
C11 C12 S1 108.4(2) . . ?
C22 C21 C16 118.7(3) . . ?
C20 C21 C22 122.2(3) . . ?
C20 C21 C16 119.1(3) . . ?
C15 C14 C13 120.5(3) . . ?
C6 C11 C12 114.4(3) . . ?
C27 C28 C23 119.5(3) . . ?
C2 C3 C8 108.5(3) . . ?
C2 C3 C10 112.5(3) . . ?
C2 C3 C4 110.7(3) . . ?
C10 C3 C8 108.2(3) . . ?
C4 C3 C8 108.5(3) . . ?
C4 C3 C10 108.3(3) . . ?
O1 C2 C3 112.4(3) . . ?
O2 C2 O1 122.1(3) . . ?
O2 C2 C3 125.5(3) . . ?
C13 C22 C21 121.7(3) . . ?
C25 C26 C29 119.3(3) . . ?
C27 C26 C25 121.0(3) . . ?
C27 C26 C29 119.8(4) . . ?
C14 C15 C16 121.2(3) . . ?
C15 C16 C21 118.7(3) . . ?
C15 C16 C17 122.8(3) . . ?
C17 C16 C21 118.5(3) . . ?
C8 C7 C6 110.2(3) . . ?
C24 C25 C26 119.6(3) . . ?
C28 C27 C26 119.8(3) . . ?
C25 C24 C23 119.0(3) . . ?
C10 C9 C6 111.5(3) . . ?
C4 C5 C6 110.8(3) . . ?
C19 C20 C21 120.6(4) . . ?
C7 C8 C3 111.3(3) . . ?
C18 C17 C16 120.9(4) . . ?
C17 C18 C19 120.5(4) . . ?
C20 C19 C18 120.3(4) . . ?
C3 C10 C9 109.6(3) . . ?
C3 C4 C5 110.8(3) . . ?
F1 C29 C26 113.5(4) . . ?
F1 C29 F2 100.8(5) . . ?
F2 C29 C26 108.8(4) . . ?
F3 C29 C26 116.0(4) . . ?
F3 C29 F1 111.5(5) . . ?
F3 C29 F2 104.5(5) . . ?
F4 C29 C26 104.3(6) . . ?
F5 C29 C26 118.9(7) . . ?
F5 C29 F4 101.6(8) . . ?
F5 C29 F6 113.3(10) . . ?
F6 C29 C26 114.0(12) . . ?
F6 C29 F4 101.8(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
