# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2100_auto
_database_code_depnum_ccdc_archive 'CCDC 2225352'
loop_
_audit_author_name
_audit_author_address
'Weiqiang Sun'
;Wuyi University
China
;
_audit_update_record             
;
2023-01-23 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 F2 N O4 S'
_chemical_formula_weight         394.40

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   21.7735(4)
_cell_length_b                   5.59738(11)
_cell_length_c                   15.2888(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.1606(17)
_cell_angle_gamma                90
_cell_volume                     1839.55(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    18441
_cell_measurement_theta_min      4.6360
_cell_measurement_theta_max      76.7330

_exptl_crystal_description       diamond
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.973
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28575
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.113
_diffrn_reflns_theta_max         77.080
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3690
_reflns_number_gt                3410
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+2.3429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S12 S 0.31487(4) 0.62367(14) 0.47080(5) 0.0508(2) Uani 1 1 d . . . . .
F17 F 0.18388(8) 0.2561(4) 0.53325(12) 0.0684(6) Uani 1 1 d . . . . .
F16 F 0.23047(10) 0.0207(3) 0.63679(15) 0.0720(6) Uani 1 1 d . . . . .
O11 O 0.27821(10) 0.5577(4) 0.54899(14) 0.0529(5) Uani 1 1 d . . . . .
O19 O 0.03649(11) 0.7464(4) 0.57163(15) 0.0619(6) Uani 1 1 d . . . . .
O13 O 0.29651(14) 0.8642(4) 0.45264(17) 0.0733(7) Uani 1 1 d . . . . .
O14 O 0.37846(11) 0.5666(6) 0.49357(19) 0.0809(8) Uani 1 1 d . . . . .
N20 N 0.04371(14) 1.1428(6) 0.5981(2) 0.0660(8) Uani 1 1 d . . . . .
H20 H 0.020483 1.149408 0.550369 0.099 Uiso 1 1 calc R U . . .
C7 C 0.15578(13) 0.5553(6) 0.66680(19) 0.0477(7) Uani 1 1 d . . . . .
H7 H 0.139778 0.590945 0.608187 0.057 Uiso 1 1 calc R U . . .
C1 C 0.12994(13) 0.6873(6) 0.73620(19) 0.0466(6) Uani 1 1 d . . . . .
C6 C 0.08538(12) 0.8693(6) 0.71470(19) 0.0474(7) Uani 1 1 d . . . . .
C21 C 0.33973(13) 0.3225(5) 0.66811(19) 0.0475(7) Uani 1 1 d . . . . .
C8 C 0.19925(14) 0.3926(6) 0.68081(19) 0.0502(7) Uani 1 1 d . . . . .
H8 H 0.215717 0.359439 0.739467 0.060 Uiso 1 1 calc R U . . .
C9 C 0.22481(14) 0.2555(6) 0.6112(2) 0.0505(7) Uani 1 1 d . . . . .
C18 C 0.05398(12) 0.9146(6) 0.6214(2) 0.0497(7) Uani 1 1 d . . . . .
C10 C 0.28838(14) 0.3236(5) 0.58928(19) 0.0476(7) Uani 1 1 d . . . . .
H10 H 0.299268 0.211708 0.544877 0.057 Uiso 1 1 calc R U . . .
C26 C 0.34843(16) 0.5015(6) 0.7309(2) 0.0611(8) Uani 1 1 d . . . . .
H26 H 0.322518 0.634493 0.724439 0.073 Uiso 1 1 calc R U . . .
C22 C 0.37979(15) 0.1291(6) 0.6793(2) 0.0598(8) Uani 1 1 d . . . . .
H22 H 0.375545 0.008297 0.637049 0.072 Uiso 1 1 calc R U . . .
C2 C 0.15008(16) 0.6389(7) 0.8253(2) 0.0611(8) Uani 1 1 d . . . . .
H2 H 0.178953 0.517450 0.840477 0.073 Uiso 1 1 calc R U . . .
C24 C 0.43446(15) 0.2888(8) 0.8163(2) 0.0642(9) Uani 1 1 d . . . . .
C5 C 0.06575(15) 0.9978(7) 0.7828(2) 0.0619(9) Uani 1 1 d . . . . .
H5 H 0.037409 1.121704 0.768895 0.074 Uiso 1 1 calc R U . . .
C25 C 0.39514(18) 0.4856(8) 0.8033(2) 0.0709(10) Uani 1 1 d . . . . .
H25 H 0.400406 0.609614 0.844302 0.085 Uiso 1 1 calc R U . . .
C23 C 0.42577(16) 0.1127(8) 0.7520(3) 0.0713(10) Uani 1 1 d . . . . .
H23 H 0.451725 -0.020232 0.758040 0.086 Uiso 1 1 calc R U . . .
C15 C 0.28200(18) 0.4465(6) 0.3815(2) 0.0643(9) Uani 1 1 d . . . . .
H15A H 0.292372 0.282029 0.394170 0.096 Uiso 1 1 calc R U . . .
H15B H 0.297942 0.494833 0.329231 0.096 Uiso 1 1 calc R U . . .
H15C H 0.237604 0.465082 0.372105 0.096 Uiso 1 1 calc R U . . .
C4 C 0.08733(17) 0.9461(8) 0.8710(2) 0.0707(10) Uani 1 1 d . . . . .
H4 H 0.073633 1.034595 0.915623 0.085 Uiso 1 1 calc R U . . .
C3 C 0.12881(17) 0.7644(8) 0.8918(2) 0.0698(10) Uani 1 1 d . . . . .
H3 H 0.142672 0.725433 0.950808 0.084 Uiso 1 1 calc R U . . .
C27 C 0.4846(2) 0.2684(11) 0.8957(3) 0.1012(17) Uani 1 1 d . . . . .
H27A H 0.502719 0.422706 0.909801 0.152 Uiso 1 1 calc R U . . .
H27B H 0.516075 0.159860 0.882811 0.152 Uiso 1 1 calc R U . . .
H27C H 0.466942 0.209584 0.945228 0.152 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
S12 O14 1.410(3) . ?
S12 O13 1.419(3) . ?
S12 O11 1.583(2) . ?
S12 C15 1.746(3) . ?
F17 C9 1.370(3) . ?
F16 C9 1.371(4) . ?
O11 C10 1.450(4) . ?
O19 C18 1.232(4) . ?
N20 C18 1.335(4) . ?
N20 H20 0.8200 . ?
C7 C8 1.306(4) . ?
C7 C1 1.476(4) . ?
C7 H7 0.9300 . ?
C1 C2 1.390(4) . ?
C1 C6 1.409(4) . ?
C6 C5 1.388(4) . ?
C6 C18 1.503(4) . ?
C21 C26 1.380(4) . ?
C21 C22 1.383(4) . ?
C21 C10 1.508(4) . ?
C8 C9 1.490(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.524(4) . ?
C10 H10 0.9800 . ?
C26 C25 1.382(5) . ?
C26 H26 0.9300 . ?
C22 C23 1.375(5) . ?
C22 H22 0.9300 . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C24 C23 1.384(6) . ?
C24 C25 1.390(6) . ?
C24 C27 1.501(5) . ?
C5 C4 1.386(5) . ?
C5 H5 0.9300 . ?
C25 H25 0.9300 . ?
C23 H23 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C4 C3 1.364(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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 S12 O13 119.88(19) . . ?
O14 S12 O11 110.74(15) . . ?
O13 S12 O11 102.07(14) . . ?
O14 S12 C15 109.19(18) . . ?
O13 S12 C15 108.57(17) . . ?
O11 S12 C15 105.34(16) . . ?
C10 O11 S12 118.06(18) . . ?
C18 N20 H20 109.5 . . ?
C8 C7 C1 125.5(3) . . ?
C8 C7 H7 117.3 . . ?
C1 C7 H7 117.3 . . ?
C2 C1 C6 117.9(3) . . ?
C2 C1 C7 120.7(3) . . ?
C6 C1 C7 121.4(3) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C18 118.5(3) . . ?
C1 C6 C18 122.4(3) . . ?
C26 C21 C22 117.9(3) . . ?
C26 C21 C10 123.7(3) . . ?
C22 C21 C10 118.4(3) . . ?
C7 C8 C9 125.8(3) . . ?
C7 C8 H8 117.1 . . ?
C9 C8 H8 117.1 . . ?
F17 C9 F16 105.5(3) . . ?
F17 C9 C8 110.8(2) . . ?
F16 C9 C8 108.5(3) . . ?
F17 C9 C10 107.2(2) . . ?
F16 C9 C10 105.0(2) . . ?
C8 C9 C10 118.9(3) . . ?
O19 C18 N20 123.0(3) . . ?
O19 C18 C6 120.4(3) . . ?
N20 C18 C6 116.5(3) . . ?
O11 C10 C21 112.8(2) . . ?
O11 C10 C9 103.7(2) . . ?
C21 C10 C9 114.0(2) . . ?
O11 C10 H10 108.7 . . ?
C21 C10 H10 108.7 . . ?
C9 C10 H10 108.7 . . ?
C21 C26 C25 120.9(3) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C3 C2 C1 122.3(3) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C23 C24 C25 116.8(3) . . ?
C23 C24 C27 121.3(4) . . ?
C25 C24 C27 121.9(4) . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C26 C25 C24 121.6(3) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C22 C23 C24 121.7(4) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
S12 C15 H15A 109.5 . . ?
S12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
O14 S12 O11 C10 -47.8(3) . . . . ?
O13 S12 O11 C10 -176.6(2) . . . . ?
C15 S12 O11 C10 70.1(2) . . . . ?
C8 C7 C1 C2 -2.0(5) . . . . ?
C8 C7 C1 C6 176.5(3) . . . . ?
C2 C1 C6 C5 2.7(5) . . . . ?
C7 C1 C6 C5 -175.8(3) . . . . ?
C2 C1 C6 C18 -171.6(3) . . . . ?
C7 C1 C6 C18 9.9(4) . . . . ?
C1 C7 C8 C9 178.8(3) . . . . ?
C7 C8 C9 F17 -21.3(5) . . . . ?
C7 C8 C9 F16 -136.7(3) . . . . ?
C7 C8 C9 C10 103.6(4) . . . . ?
C5 C6 C18 O19 -132.9(3) . . . . ?
C1 C6 C18 O19 41.4(4) . . . . ?
C5 C6 C18 N20 43.8(4) . . . . ?
C1 C6 C18 N20 -141.9(3) . . . . ?
S12 O11 C10 C21 91.7(3) . . . . ?
S12 O11 C10 C9 -144.5(2) . . . . ?
C26 C21 C10 O11 40.8(4) . . . . ?
C22 C21 C10 O11 -140.5(3) . . . . ?
C26 C21 C10 C9 -77.2(4) . . . . ?
C22 C21 C10 C9 101.5(3) . . . . ?
F17 C9 C10 O11 59.1(3) . . . . ?
F16 C9 C10 O11 171.0(2) . . . . ?
C8 C9 C10 O11 -67.5(3) . . . . ?
F17 C9 C10 C21 -177.9(2) . . . . ?
F16 C9 C10 C21 -66.0(3) . . . . ?
C8 C9 C10 C21 55.6(4) . . . . ?
C22 C21 C26 C25 -1.0(5) . . . . ?
C10 C21 C26 C25 177.8(3) . . . . ?
C26 C21 C22 C23 1.7(5) . . . . ?
C10 C21 C22 C23 -177.1(3) . . . . ?
C6 C1 C2 C3 -1.1(5) . . . . ?
C7 C1 C2 C3 177.5(3) . . . . ?
C1 C6 C5 C4 -2.2(5) . . . . ?
C18 C6 C5 C4 172.3(3) . . . . ?
C21 C26 C25 C24 -0.8(6) . . . . ?
C23 C24 C25 C26 1.9(6) . . . . ?
C27 C24 C25 C26 -178.9(4) . . . . ?
C21 C22 C23 C24 -0.7(6) . . . . ?
C25 C24 C23 C22 -1.1(6) . . . . ?
C27 C24 C23 C22 179.6(4) . . . . ?
C6 C5 C4 C3 -0.1(6) . . . . ?
C5 C4 C3 C2 1.8(6) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?

_refine_diff_density_max         0.601
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.052



