# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_11a
_audit_block_doi                 10.5517/ccdc.csd.cc2ldh8s
_database_code_depnum_ccdc_archive 'CCDC 2395285'
loop_
_audit_author_name
_audit_author_address
liqiuyun
;Yancheng Institute Of Technology
China
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 F N3 S'
_chemical_formula_weight         449.53

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'
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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   12.1973(15)
_cell_length_b                   8.1592(10)
_cell_length_c                   22.874(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.147(2)
_cell_angle_gamma                90.00
_cell_volume                     2274.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5439
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13636
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.90
_reflns_number_total             5324
_reflns_number_gt                3948
_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)+(0.0802P)²+0.4862P] 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         5324
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.27966(6) 0.60905(7) 0.22662(2) 0.0674(2) Uani 1 1 d . . .
N1 N 0.19597(12) -0.24602(19) 0.00498(6) 0.0442(3) Uani 1 1 d . . .
N2 N 0.37694(12) -0.29328(19) 0.00002(7) 0.0466(4) Uani 1 1 d . . .
F F 0.01090(9) -0.21118(17) 0.00368(6) 0.0654(4) Uani 1 1 d . . .
C1 C 0.30263(14) -0.2022(2) 0.02211(7) 0.0417(4) Uani 1 1 d . . .
C14 C 0.30522(16) 0.1080(2) 0.03203(8) 0.0475(4) Uani 1 1 d . . .
H14A H 0.3683 0.1237 0.0080 0.057 Uiso 1 1 calc R . .
H14B H 0.2402 0.1065 0.0063 0.057 Uiso 1 1 calc R . .
C24 C 0.31841(15) -0.4088(2) -0.03427(8) 0.0441(4) Uani 1 1 d . . .
C15 C 0.29770(15) 0.2494(2) 0.07401(8) 0.0447(4) Uani 1 1 d . . .
C20 C 0.19700(16) 0.3038(2) 0.09171(9) 0.0532(5) Uani 1 1 d . . .
H20 H 0.1336 0.2637 0.0730 0.064 Uiso 1 1 calc R . .
C23 C 0.20569(15) -0.3820(2) -0.03212(7) 0.0444(4) Uani 1 1 d . . .
C18 C 0.28133(17) 0.4800(2) 0.16455(8) 0.0493(4) Uani 1 1 d . . .
C3 C 0.22841(16) -0.0844(2) 0.11117(8) 0.0479(4) Uani 1 1 d . . .
H3A H 0.2456 -0.1817 0.1341 0.057 Uiso 1 1 calc R . .
H3B H 0.2299 0.0090 0.1374 0.057 Uiso 1 1 calc R . .
C13 C -0.23720(16) 0.1255(3) 0.14992(9) 0.0535(5) Uani 1 1 d . . .
H13 H -0.2609 0.0622 0.1181 0.064 Uiso 1 1 calc R . .
C5 C 0.10601(14) -0.1834(2) 0.03273(8) 0.0470(4) Uani 1 1 d . . .
C4 C 0.11454(15) -0.1016(2) 0.08280(8) 0.0477(4) Uani 1 1 d . . .
C2 C 0.31612(14) -0.0612(2) 0.06444(8) 0.0434(4) Uani 1 1 d . . .
C17 C 0.38260(17) 0.4356(2) 0.14397(9) 0.0549(5) Uani 1 1 d . . .
H17 H 0.4459 0.4832 0.1603 0.066 Uiso 1 1 calc R . .
C7 C -0.04657(16) 0.0399(3) 0.13544(9) 0.0548(5) Uani 1 1 d . . .
C22 C 0.42534(17) -0.0734(3) 0.09404(9) 0.0560(5) Uani 1 1 d . . .
C19 C 0.18774(17) 0.4167(3) 0.13668(9) 0.0562(5) Uani 1 1 d . . .
H19 H 0.1188 0.4497 0.1481 0.067 Uiso 1 1 calc R . .
C8 C -0.12692(16) 0.1294(2) 0.16669(8) 0.0478(4) Uani 1 1 d . . .
C16 C 0.39101(16) 0.3223(2) 0.09972(9) 0.0526(5) Uani 1 1 d . . .
H16 H 0.4599 0.2939 0.0868 0.063 Uiso 1 1 calc R . .
C25 C 0.35783(18) -0.5389(2) -0.06645(9) 0.0547(5) Uani 1 1 d . . .
H25 H 0.4326 -0.5610 -0.0673 0.066 Uiso 1 1 calc R . .
C6 C 0.02343(17) -0.0291(3) 0.10996(9) 0.0539(5) Uani 1 1 d . . .
C26 C 0.2823(2) -0.6342(3) -0.09705(10) 0.0645(6) Uani 1 1 d . . .
H26 H 0.3067 -0.7212 -0.1194 0.077 Uiso 1 1 calc R . .
C28 C 0.12929(18) -0.4774(3) -0.06239(9) 0.0592(5) Uani 1 1 d . . .
H28 H 0.0543 -0.4580 -0.0607 0.071 Uiso 1 1 calc R . .
C27 C 0.1707(2) -0.6034(3) -0.09525(10) 0.0676(6) Uani 1 1 d . . .
H27 H 0.1222 -0.6697 -0.1169 0.081 Uiso 1 1 calc R . .
C9 C -0.09267(19) 0.2225(3) 0.21520(10) 0.0623(5) Uani 1 1 d . . .
H9 H -0.0190 0.2246 0.2272 0.075 Uiso 1 1 calc R . .
C11 C -0.2768(2) 0.3084(3) 0.22773(11) 0.0786(7) Uani 1 1 d . . .
H11 H -0.3273 0.3696 0.2480 0.094 Uiso 1 1 calc R . .
C12 C -0.31167(19) 0.2151(3) 0.18024(11) 0.0679(6) Uani 1 1 d . . .
H12 H -0.3856 0.2129 0.1688 0.082 Uiso 1 1 calc R . .
N3 N 0.50814(18) -0.0785(3) 0.11795(11) 0.0865(7) Uani 1 1 d . . .
C10 C -0.1683(2) 0.3111(3) 0.24508(11) 0.0767(7) Uani 1 1 d . . .
H10 H -0.1456 0.3734 0.2774 0.092 Uiso 1 1 calc R . .
C21 C 0.1390(3) 0.6260(4) 0.24119(14) 0.1000(10) Uani 1 1 d . . .
H21A H 0.1020 0.6859 0.2102 0.150 Uiso 1 1 calc R . .
H21B H 0.1309 0.6828 0.2775 0.150 Uiso 1 1 calc R . .
H21C H 0.1075 0.5185 0.2438 0.150 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 C21 1.766(3) . ?
S1 C18 1.7682(19) . ?
N1 C5 1.386(2) . ?
N1 C1 1.391(2) . ?
N1 C23 1.404(2) . ?
N2 C1 1.290(2) . ?
N2 C24 1.404(2) . ?
F C5 1.334(2) . ?
C1 C2 1.509(2) . ?
C14 C15 1.506(3) . ?
C14 C2 1.570(3) . ?
C24 C25 1.388(3) . ?
C24 C23 1.395(3) . ?
C15 C20 1.381(3) . ?
C15 C16 1.394(3) . ?
C20 C19 1.388(3) . ?
C23 C28 1.381(3) . ?
C18 C17 1.386(3) . ?
C18 C19 1.386(3) . ?
C3 C4 1.517(3) . ?
C3 C2 1.552(3) . ?
C13 C12 1.374(3) . ?
C13 C8 1.385(3) . ?
C5 C4 1.327(3) . ?
C4 C6 1.422(3) . ?
C2 C22 1.475(3) . ?
C17 C16 1.378(3) . ?
C7 C6 1.193(3) . ?
C7 C8 1.435(3) . ?
C22 N3 1.131(3) . ?
C8 C9 1.396(3) . ?
C25 C26 1.376(3) . ?
C26 C27 1.387(3) . ?
C28 C27 1.380(3) . ?
C9 C10 1.375(3) . ?
C11 C10 1.367(4) . ?
C11 C12 1.381(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
C21 S1 C18 103.81(12) . . ?
C5 N1 C1 121.62(15) . . ?
C5 N1 C23 130.85(16) . . ?
C1 N1 C23 105.91(14) . . ?
C1 N2 C24 104.81(15) . . ?
N2 C1 N1 113.88(16) . . ?
N2 C1 C2 129.02(16) . . ?
N1 C1 C2 117.08(15) . . ?
C15 C14 C2 112.25(14) . . ?
C25 C24 C23 120.01(18) . . ?
C25 C24 N2 129.11(18) . . ?
C23 C24 N2 110.87(16) . . ?
C20 C15 C16 117.40(18) . . ?
C20 C15 C14 120.62(17) . . ?
C16 C15 C14 121.82(17) . . ?
C15 C20 C19 121.90(18) . . ?
C28 C23 C24 122.79(18) . . ?
C28 C23 N1 132.69(18) . . ?
C24 C23 N1 104.52(15) . . ?
C17 C18 C19 118.38(18) . . ?
C17 C18 S1 117.73(15) . . ?
C19 C18 S1 123.85(16) . . ?
C4 C3 C2 111.11(14) . . ?
C12 C13 C8 120.1(2) . . ?
C4 C5 F 123.64(17) . . ?
C4 C5 N1 122.91(17) . . ?
F C5 N1 113.45(16) . . ?
C5 C4 C6 123.30(18) . . ?
C5 C4 C3 117.17(16) . . ?
C6 C4 C3 119.52(17) . . ?
C22 C2 C1 108.53(15) . . ?
C22 C2 C3 108.03(16) . . ?
C1 C2 C3 106.69(15) . . ?
C22 C2 C14 109.59(16) . . ?
C1 C2 C14 111.23(14) . . ?
C3 C2 C14 112.61(14) . . ?
C16 C17 C18 121.10(18) . . ?
C6 C7 C8 177.1(2) . . ?
N3 C22 C2 177.6(2) . . ?
C18 C19 C20 119.97(19) . . ?
C13 C8 C9 119.43(19) . . ?
C13 C8 C7 121.64(18) . . ?
C9 C8 C7 118.92(19) . . ?
C17 C16 C15 120.93(19) . . ?
C26 C25 C24 117.6(2) . . ?
C7 C6 C4 174.3(2) . . ?
C25 C26 C27 121.5(2) . . ?
C27 C28 C23 116.1(2) . . ?
C28 C27 C26 122.1(2) . . ?
C10 C9 C8 119.7(2) . . ?
C10 C11 C12 120.2(2) . . ?
C13 C12 C11 120.0(2) . . ?
C11 C10 C9 120.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.90
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.057
