# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_220710e
_database_code_depnum_ccdc_archive 'CCDC 2204064'
loop_
_audit_author_name
_audit_author_address
'Huan Xiong'
;Wuhan University of Technology
China
;
_audit_update_record             
;
2022-08-29 deposited with the CCDC.	2022-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 F N O4 S'
_chemical_formula_weight         383.38

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.5757(4)
_cell_length_b                   10.3900(11)
_cell_length_c                   18.9149(18)
_cell_angle_alpha                76.640(2)
_cell_angle_beta                 83.509(3)
_cell_angle_gamma                83.568(3)
_cell_volume                     865.86(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1400
_cell_measurement_theta_min      2.262
_cell_measurement_theta_max      25.124

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9057
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4275
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2988
_reflns_number_gt                2052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.3820P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.3136(2) 0.38634(9) 0.33566(6) 0.0471(3) Uani 1 1 d . . .
F1 F -0.0623(5) 0.2754(2) 0.35999(15) 0.0778(8) Uani 1 1 d . . .
N1 N 0.0789(6) 0.7139(3) 0.30276(14) 0.0366(7) Uani 1 1 d . . .
O1 O 0.0469(7) 0.9120(2) 0.16260(14) 0.0611(8) Uani 1 1 d . . .
O2 O 0.8072(8) 0.6697(3) -0.08666(15) 0.0718(9) Uani 1 1 d . . .
O3 O -0.4970(6) 0.3898(3) 0.40036(16) 0.0706(9) Uani 1 1 d . . .
O4 O -0.4197(7) 0.3511(3) 0.27589(16) 0.0663(8) Uani 1 1 d . . .
C1 C 0.1097(8) 0.6912(3) 0.23108(19) 0.0406(8) Uani 1 1 d . . .
C2 C -0.0129(8) 0.5750(3) 0.23420(19) 0.0416(9) Uani 1 1 d . . .
H2 H -0.0189 0.5350 0.1953 0.050 Uiso 1 1 calc R . .
C3 C -0.1285(8) 0.5268(3) 0.3070(2) 0.0425(9) Uani 1 1 d . . .
C4 C -0.0714(7) 0.6135(3) 0.34927(19) 0.0397(8) Uani 1 1 d . . .
C5 C -0.1428(8) 0.6171(4) 0.42379(19) 0.0478(9) Uani 1 1 d . . .
H5 H -0.2499 0.5521 0.4547 0.057 Uiso 1 1 calc R . .
C6 C -0.0538(9) 0.7158(4) 0.4494(2) 0.0507(10) Uani 1 1 d . . .
H6 H -0.1089 0.7205 0.4977 0.061 Uiso 1 1 calc R . .
C7 C 0.1246(8) 0.8139(3) 0.4038(2) 0.0436(9) Uani 1 1 d . . .
C8 C 0.2035(7) 0.8097(3) 0.3303(2) 0.0396(8) Uani 1 1 d . . .
C9 C 0.4033(8) 0.8948(3) 0.2878(2) 0.0477(9) Uani 1 1 d . . .
H9 H 0.4641 0.8884 0.2400 0.057 Uiso 1 1 calc R . .
C10 C 0.5106(9) 0.9887(4) 0.3170(3) 0.0586(11) Uani 1 1 d . . .
H10 H 0.6440 1.0452 0.2886 0.070 Uiso 1 1 calc R . .
C11 C 0.4209(10) 0.9996(4) 0.3884(3) 0.0636(12) Uani 1 1 d . . .
H11 H 0.4839 1.0666 0.4066 0.076 Uiso 1 1 calc R . .
C12 C 0.2387(9) 0.9106(4) 0.4318(2) 0.0572(11) Uani 1 1 d . . .
H12 H 0.1900 0.9142 0.4804 0.069 Uiso 1 1 calc R . .
C13 C 0.1528(8) 0.7977(3) 0.16263(19) 0.0438(9) Uani 1 1 d . . .
C14 C 0.3141(8) 0.7585(3) 0.09790(18) 0.0403(9) Uani 1 1 d . . .
C15 C 0.3076(9) 0.8505(4) 0.0307(2) 0.0540(10) Uani 1 1 d . . .
H15 H 0.1942 0.9312 0.0284 0.065 Uiso 1 1 calc R . .
C16 C 0.4646(10) 0.8248(4) -0.0321(2) 0.0612(12) Uani 1 1 d . . .
H16 H 0.4543 0.8867 -0.0762 0.073 Uiso 1 1 calc R . .
C17 C 0.6381(10) 0.7052(4) -0.0285(2) 0.0514(10) Uani 1 1 d . . .
C18 C 0.6470(9) 0.6116(3) 0.0377(2) 0.0480(10) Uani 1 1 d . . .
H18 H 0.7611 0.5311 0.0400 0.058 Uiso 1 1 calc R . .
C19 C 0.4874(8) 0.6386(3) 0.09931(19) 0.0445(9) Uani 1 1 d . . .
H19 H 0.4948 0.5756 0.1430 0.053 Uiso 1 1 calc R . .
C20 C 0.8117(15) 0.7642(5) -0.1553(2) 0.097(2) Uani 1 1 d . . .
H20A H 0.6174 0.7796 -0.1719 0.145 Uiso 1 1 calc R . .
H20B H 0.9472 0.7299 -0.1905 0.145 Uiso 1 1 calc R . .
H20C H 0.8734 0.8461 -0.1495 0.145 Uiso 1 1 calc R . .


_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 1.409(3) . ?
S1 O4 1.415(3) . ?
S1 F1 1.562(2) . ?
S1 C3 1.717(3) . ?
N1 C4 1.391(4) . ?
N1 C1 1.418(4) . ?
N1 C8 1.422(4) . ?
O1 C13 1.231(4) . ?
O2 C17 1.370(5) . ?
O2 C20 1.435(5) . ?
C1 C2 1.374(5) . ?
C1 C13 1.506(5) . ?
C2 C3 1.415(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(5) . ?
C4 C5 1.419(5) . ?
C5 C6 1.350(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.405(5) . ?
C7 C12 1.409(5) . ?
C8 C9 1.398(5) . ?
C9 C10 1.384(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.473(5) . ?
C14 C19 1.396(5) . ?
C14 C15 1.403(5) . ?
C15 C16 1.383(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.399(5) . ?
C18 C19 1.372(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O3 S1 O4 121.11(18) . . ?
O3 S1 F1 104.13(18) . . ?
O4 S1 F1 104.44(17) . . ?
O3 S1 C3 111.28(18) . . ?
O4 S1 C3 110.74(17) . . ?
F1 S1 C3 103.04(16) . . ?
C4 N1 C1 109.1(3) . . ?
C4 N1 C8 121.1(3) . . ?
C1 N1 C8 129.4(3) . . ?
C17 O2 C20 117.6(3) . . ?
C2 C1 N1 107.4(3) . . ?
C2 C1 C13 124.1(3) . . ?
N1 C1 C13 124.4(3) . . ?
C1 C2 C3 108.1(3) . . ?
C1 C2 H2 125.9 . . ?
C3 C2 H2 125.9 . . ?
C4 C3 C2 108.6(3) . . ?
C4 C3 S1 127.1(3) . . ?
C2 C3 S1 124.3(3) . . ?
N1 C4 C3 106.8(3) . . ?
N1 C4 C5 120.0(3) . . ?
C3 C4 C5 133.2(3) . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C12 118.4(4) . . ?
C8 C7 C6 119.8(3) . . ?
C12 C7 C6 121.7(4) . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 N1 122.4(3) . . ?
C7 C8 N1 117.4(3) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.5(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 121.1(4) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O1 C13 C14 123.1(3) . . ?
O1 C13 C1 119.1(3) . . ?
C14 C13 C1 117.8(3) . . ?
C19 C14 C15 117.4(3) . . ?
C19 C14 C13 124.4(3) . . ?
C15 C14 C13 118.1(3) . . ?
C16 C15 C14 122.0(4) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 119.0(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
O2 C17 C16 124.4(3) . . ?
O2 C17 C18 115.6(4) . . ?
C16 C17 C18 120.0(4) . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.6(3) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 N1 C1 C2 -1.9(4) . . . . ?
C8 N1 C1 C2 170.5(3) . . . . ?
C4 N1 C1 C13 156.1(3) . . . . ?
C8 N1 C1 C13 -31.5(5) . . . . ?
N1 C1 C2 C3 1.8(4) . . . . ?
C13 C1 C2 C3 -156.3(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C2 C3 S1 177.7(3) . . . . ?
O3 S1 C3 C4 21.4(4) . . . . ?
O4 S1 C3 C4 159.1(3) . . . . ?
F1 S1 C3 C4 -89.7(4) . . . . ?
O3 S1 C3 C2 -157.1(3) . . . . ?
O4 S1 C3 C2 -19.3(4) . . . . ?
F1 S1 C3 C2 91.9(3) . . . . ?
C1 N1 C4 C3 1.3(4) . . . . ?
C8 N1 C4 C3 -171.9(3) . . . . ?
C1 N1 C4 C5 -177.0(3) . . . . ?
C8 N1 C4 C5 9.8(5) . . . . ?
C2 C3 C4 N1 -0.2(4) . . . . ?
S1 C3 C4 N1 -178.9(3) . . . . ?
C2 C3 C4 C5 177.8(4) . . . . ?
S1 C3 C4 C5 -0.9(6) . . . . ?
N1 C4 C5 C6 -2.5(5) . . . . ?
C3 C4 C5 C6 179.8(4) . . . . ?
C4 C5 C6 C7 -3.1(6) . . . . ?
C5 C6 C7 C8 1.5(6) . . . . ?
C5 C6 C7 C12 -174.6(4) . . . . ?
C12 C7 C8 C9 3.5(5) . . . . ?
C6 C7 C8 C9 -172.8(3) . . . . ?
C12 C7 C8 N1 -178.2(3) . . . . ?
C6 C7 C8 N1 5.5(5) . . . . ?
C4 N1 C8 C9 167.1(3) . . . . ?
C1 N1 C8 C9 -4.6(5) . . . . ?
C4 N1 C8 C7 -11.2(5) . . . . ?
C1 N1 C8 C7 177.2(3) . . . . ?
C7 C8 C9 C10 -3.7(5) . . . . ?
N1 C8 C9 C10 178.1(3) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C12 4.2(6) . . . . ?
C10 C11 C12 C7 -4.4(6) . . . . ?
C8 C7 C12 C11 0.5(6) . . . . ?
C6 C7 C12 C11 176.7(4) . . . . ?
C2 C1 C13 O1 124.7(4) . . . . ?
N1 C1 C13 O1 -29.7(5) . . . . ?
C2 C1 C13 C14 -53.6(5) . . . . ?
N1 C1 C13 C14 152.0(3) . . . . ?
O1 C13 C14 C19 166.3(4) . . . . ?
C1 C13 C14 C19 -15.5(5) . . . . ?
O1 C13 C14 C15 -10.0(6) . . . . ?
C1 C13 C14 C15 168.3(3) . . . . ?
C19 C14 C15 C16 0.2(6) . . . . ?
C13 C14 C15 C16 176.7(4) . . . . ?
C14 C15 C16 C17 -1.1(7) . . . . ?
C20 O2 C17 C16 1.9(6) . . . . ?
C20 O2 C17 C18 -178.3(4) . . . . ?
C15 C16 C17 O2 -178.8(4) . . . . ?
C15 C16 C17 C18 1.4(6) . . . . ?
O2 C17 C18 C19 179.3(3) . . . . ?
C16 C17 C18 C19 -0.8(6) . . . . ?
C17 C18 C19 C14 -0.1(6) . . . . ?
C15 C14 C19 C18 0.4(6) . . . . ?
C13 C14 C19 C18 -175.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.056
