# 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_t
_database_code_depnum_ccdc_archive 'CCDC 2393566'
loop_
_audit_author_name
_audit_author_address
'Wenya Zheng'
;Xinjiang Normal University
China
;
_audit_update_record             
;
2024-10-24 deposited with the CCDC.	2025-04-08 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         'C26 H32 N2 O5 S'
_chemical_formula_sum            'C26 H32 N2 O5 S'
_chemical_formula_weight         484.59

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'
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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.01700(10)
_cell_length_b                   8.34540(10)
_cell_length_c                   13.59930(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.8290(10)
_cell_angle_gamma                90
_cell_volume                     1247.55(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13726
_cell_measurement_theta_min      3.2550
_cell_measurement_theta_max      77.7490

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.474
_shelx_estimated_absorpt_T_min   0.798
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16788
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.257
_diffrn_reflns_theta_max         77.031
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             4574
_reflns_number_gt                4493
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.779
_reflns_Friedel_fraction_full    0.854

_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)+(0.0359P)²+0.1788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4574
_refine_ls_number_parameters     317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0615
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C2 C 0.04791(16) 0.6237(2) 0.23275(13) 0.0194(4) Uani 1 1 d . . . . .
O2 O 0.18743(11) 0.31390(16) 0.28204(9) 0.0194(3) Uani 1 1 d . . . . .
N2 N 0.38435(13) 0.53289(19) 0.44153(10) 0.0155(3) Uani 1 1 d . . . . .
H2 H 0.439842 0.551566 0.489738 0.019 Uiso 1 1 calc R U . . .
C11 C 0.24665(15) 0.4111(2) 0.33065(12) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.17116(15) 0.6552(2) 0.24381(12) 0.0169(3) Uani 1 1 d . . . . .
S1 S 0.35603(4) 0.84361(6) 0.39804(3) 0.02033(11) Uani 1 1 d . . . . .
N1 N 0.24390(12) 0.57556(19) 0.32084(10) 0.0160(3) Uani 1 1 d . . . . .
O1 O -0.02818(12) 0.8695(2) 0.01161(9) 0.0287(3) Uani 1 1 d . . . . .
H1 H 0.013(2) 0.553(3) 0.2776(16) 0.020(5) Uiso 1 1 d . . . . .
C4 C 0.03044(17) 0.7937(2) 0.09031(13) 0.0215(4) Uani 1 1 d . . . . .
O4 O 0.47797(10) 0.37155(16) 0.28513(8) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.15455(16) 0.8277(3) 0.10332(12) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.190499 0.900448 0.060043 0.029 Uiso 1 1 calc R U . . .
O5 O 0.16439(11) 0.57937(18) 0.77268(9) 0.0230(3) Uani 1 1 d . . . . .
C3 C -0.02317(16) 0.6917(3) 0.15480(13) 0.0224(4) Uani 1 1 d . . . . .
H3 H -0.107575 0.668189 0.146145 0.027 Uiso 1 1 calc R U . . .
O3 O 0.49018(10) 0.15877(16) 0.38710(8) 0.0186(3) Uani 1 1 d . . . . .
C14 C 0.44743(14) 0.2853(2) 0.36186(11) 0.0148(4) Uani 1 1 d . . . . .
C13 C 0.22259(15) 0.4348(2) 0.63582(12) 0.0179(4) Uani 1 1 d . . . . .
H13 H 0.304368 0.445211 0.661920 0.021 Uiso 1 1 calc R U . . .
C9 C 0.19746(14) 0.3514(2) 0.54871(11) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.34504(14) 0.3733(2) 0.41271(11) 0.0152(4) Uani 1 1 d . . . . .
C17 C 0.67161(16) 0.4451(3) 0.22835(13) 0.0212(4) Uani 1 1 d . . . . .
H17 H 0.733835 0.414588 0.181460 0.025 Uiso 1 1 calc R U . . .
C6 C 0.22558(16) 0.7562(3) 0.17888(13) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.310609 0.776143 0.186129 0.025 Uiso 1 1 calc R U . . .
C25 C 0.07640(15) 0.3368(3) 0.51086(12) 0.0209(4) Uani 1 1 d . . . . .
H25 H 0.057742 0.279494 0.451391 0.025 Uiso 1 1 calc R U . . .
C24 C -0.01588(16) 0.4063(3) 0.56066(13) 0.0230(4) Uani 1 1 d . . . . .
H24 H -0.097664 0.396643 0.534453 0.028 Uiso 1 1 calc R U . . .
C23 C 0.00878(16) 0.4903(2) 0.64848(13) 0.0204(4) Uani 1 1 d . . . . .
H23 H -0.055203 0.537182 0.682127 0.024 Uiso 1 1 calc R U . . .
C12 C 0.29911(15) 0.2719(2) 0.49653(12) 0.0169(3) Uani 1 1 d . . . . .
H12A H 0.269632 0.167778 0.469407 0.020 Uiso 1 1 calc R U . . .
H12B H 0.367919 0.249920 0.545248 0.020 Uiso 1 1 calc R U . . .
C16 C 0.57486(15) 0.3131(2) 0.22464(12) 0.0186(4) Uani 1 1 d . . . . .
H16 H 0.611118 0.213705 0.255392 0.022 Uiso 1 1 calc R U . . .
C15 C 0.12871(16) 0.5038(2) 0.68560(12) 0.0182(4) Uani 1 1 d . . . . .
C19 C 0.51193(17) 0.2705(3) 0.12406(13) 0.0257(4) Uani 1 1 d . . . . .
H19 H 0.464884 0.365927 0.098428 0.031 Uiso 1 1 calc R U . . .
C8 C 0.32855(14) 0.6498(2) 0.38810(11) 0.0163(4) Uani 1 1 d . . . . .
C7 C -0.15503(18) 0.8377(4) -0.00740(15) 0.0369(5) Uani 1 1 d . . . . .
H7A H -0.185530 0.896260 -0.066438 0.055 Uiso 1 1 calc R U . . .
H7B H -0.199134 0.872532 0.049080 0.055 Uiso 1 1 calc R U . . .
H7C H -0.167411 0.722510 -0.017869 0.055 Uiso 1 1 calc R U . . .
C26 C 0.07295(16) 0.6674(3) 0.81975(13) 0.0239(4) Uani 1 1 d . . . . .
H26A H 0.040175 0.751615 0.775297 0.036 Uiso 1 1 calc R U . . .
H26B H 0.108859 0.716198 0.880469 0.036 Uiso 1 1 calc R U . . .
H26C H 0.007235 0.594705 0.835703 0.036 Uiso 1 1 calc R U . . .
C22 C 0.62090(19) 0.6089(3) 0.19657(15) 0.0299(5) Uani 1 1 d . . . . .
H22A H 0.585527 0.602577 0.128622 0.045 Uiso 1 1 calc R U . . .
H22B H 0.686682 0.688163 0.200458 0.045 Uiso 1 1 calc R U . . .
H22C H 0.557960 0.641028 0.240244 0.045 Uiso 1 1 calc R U . . .
C18 C 0.73581(17) 0.4517(3) 0.33189(14) 0.0258(4) Uani 1 1 d . . . . .
H18A H 0.675743 0.472223 0.380386 0.039 Uiso 1 1 calc R U . . .
H18B H 0.796310 0.537977 0.334732 0.039 Uiso 1 1 calc R U . . .
H18C H 0.776389 0.349212 0.346698 0.039 Uiso 1 1 calc R U . . .
C21 C 0.42391(18) 0.1315(3) 0.13424(15) 0.0335(5) Uani 1 1 d . . . . .
H21A H 0.468380 0.038449 0.161880 0.050 Uiso 1 1 calc R U . . .
H21B H 0.385789 0.104041 0.069259 0.050 Uiso 1 1 calc R U . . .
H21C H 0.360958 0.162788 0.178122 0.050 Uiso 1 1 calc R U . . .
C20 C 0.6068(2) 0.2282(4) 0.05134(15) 0.0430(7) Uani 1 1 d . . . . .
H20A H 0.657138 0.322450 0.040212 0.065 Uiso 1 1 calc R U . . .
H20B H 0.565654 0.193990 -0.011273 0.065 Uiso 1 1 calc R U . . .
H20C H 0.658417 0.141048 0.078424 0.065 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
C2 C1 1.381(2) . ?
C2 C3 1.396(3) . ?
O2 C11 1.209(2) . ?
N2 C8 1.341(2) . ?
N2 C10 1.447(2) . ?
C11 N1 1.379(3) . ?
C11 C10 1.536(2) . ?
C1 C6 1.386(3) . ?
C1 N1 1.438(2) . ?
S1 C8 1.650(2) . ?
N1 C8 1.406(2) . ?
O1 C4 1.367(2) . ?
O1 C7 1.429(2) . ?
C4 C3 1.383(3) . ?
C4 C5 1.396(3) . ?
O4 C14 1.330(2) . ?
O4 C16 1.4736(19) . ?
C5 C6 1.385(3) . ?
O5 C15 1.376(2) . ?
O5 C26 1.432(2) . ?
O3 C14 1.197(2) . ?
C14 C10 1.547(2) . ?
C13 C9 1.386(3) . ?
C13 C15 1.398(2) . ?
C9 C25 1.403(2) . ?
C9 C12 1.518(2) . ?
C10 C12 1.533(2) . ?
C17 C22 1.528(3) . ?
C17 C16 1.532(3) . ?
C17 C18 1.534(2) . ?
C25 C24 1.386(3) . ?
C24 C23 1.396(3) . ?
C23 C15 1.387(2) . ?
C16 C19 1.533(2) . ?
C19 C21 1.524(3) . ?
C19 C20 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
C1 C2 C3 120.20(17) . . ?
C8 N2 C10 113.89(13) . . ?
O2 C11 N1 127.37(16) . . ?
O2 C11 C10 126.03(17) . . ?
N1 C11 C10 106.54(15) . . ?
C2 C1 C6 120.68(16) . . ?
C2 C1 N1 119.16(16) . . ?
C6 C1 N1 120.09(15) . . ?
C11 N1 C8 111.48(14) . . ?
C11 N1 C1 122.53(15) . . ?
C8 N1 C1 125.70(15) . . ?
C4 O1 C7 117.44(16) . . ?
O1 C4 C3 125.57(17) . . ?
O1 C4 C5 114.36(17) . . ?
C3 C4 C5 120.07(17) . . ?
C14 O4 C16 119.31(14) . . ?
C6 C5 C4 120.44(18) . . ?
C15 O5 C26 116.80(14) . . ?
C4 C3 C2 119.36(16) . . ?
O3 C14 O4 125.98(15) . . ?
O3 C14 C10 125.12(15) . . ?
O4 C14 C10 108.89(15) . . ?
C9 C13 C15 120.60(16) . . ?
C13 C9 C25 119.22(16) . . ?
C13 C9 C12 120.51(14) . . ?
C25 C9 C12 120.24(15) . . ?
N2 C10 C12 114.50(13) . . ?
N2 C10 C11 101.05(14) . . ?
C12 C10 C11 113.69(14) . . ?
N2 C10 C14 110.14(13) . . ?
C12 C10 C14 110.92(14) . . ?
C11 C10 C14 105.85(12) . . ?
C22 C17 C16 113.19(15) . . ?
C22 C17 C18 111.41(17) . . ?
C16 C17 C18 109.47(15) . . ?
C5 C6 C1 119.21(16) . . ?
C24 C25 C9 119.66(17) . . ?
C25 C24 C23 121.41(16) . . ?
C15 C23 C24 118.59(16) . . ?
C9 C12 C10 113.38(15) . . ?
O4 C16 C17 105.77(14) . . ?
O4 C16 C19 105.87(13) . . ?
C17 C16 C19 117.93(15) . . ?
O5 C15 C23 124.13(15) . . ?
O5 C15 C13 115.32(15) . . ?
C23 C15 C13 120.52(16) . . ?
C21 C19 C20 110.5(2) . . ?
C21 C19 C16 110.35(16) . . ?
C20 C19 C16 110.06(15) . . ?
N2 C8 N1 107.00(15) . . ?
N2 C8 S1 126.44(13) . . ?
N1 C8 S1 126.55(14) . . ?

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
C3 C2 C1 C6 1.0(3) . . . . ?
C3 C2 C1 N1 -175.99(17) . . . . ?
O2 C11 N1 C8 -177.89(15) . . . . ?
C10 C11 N1 C8 -0.68(18) . . . . ?
O2 C11 N1 C1 -3.8(3) . . . . ?
C10 C11 N1 C1 173.45(13) . . . . ?
C2 C1 N1 C11 54.7(2) . . . . ?
C6 C1 N1 C11 -122.30(19) . . . . ?
C2 C1 N1 C8 -132.03(18) . . . . ?
C6 C1 N1 C8 51.0(2) . . . . ?
C7 O1 C4 C3 -1.7(3) . . . . ?
C7 O1 C4 C5 178.8(2) . . . . ?
O1 C4 C5 C6 -178.51(18) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
O1 C4 C3 C2 -179.42(18) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C16 O4 C14 O3 -1.5(3) . . . . ?
C16 O4 C14 C10 179.60(13) . . . . ?
C15 C13 C9 C25 0.0(3) . . . . ?
C15 C13 C9 C12 -177.98(16) . . . . ?
C8 N2 C10 C12 -124.78(15) . . . . ?
C8 N2 C10 C11 -2.17(17) . . . . ?
C8 N2 C10 C14 109.42(15) . . . . ?
O2 C11 C10 N2 178.88(15) . . . . ?
N1 C11 C10 N2 1.62(16) . . . . ?
O2 C11 C10 C12 -57.9(2) . . . . ?
N1 C11 C10 C12 124.79(15) . . . . ?
O2 C11 C10 C14 64.0(2) . . . . ?
N1 C11 C10 C14 -113.21(15) . . . . ?
O3 C14 C10 N2 124.18(17) . . . . ?
O4 C14 C10 N2 -56.95(16) . . . . ?
O3 C14 C10 C12 -3.6(2) . . . . ?
O4 C14 C10 C12 175.25(13) . . . . ?
O3 C14 C10 C11 -127.38(18) . . . . ?
O4 C14 C10 C11 51.49(18) . . . . ?
C4 C5 C6 C1 -2.5(3) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
N1 C1 C6 C5 177.97(18) . . . . ?
C13 C9 C25 C24 0.3(3) . . . . ?
C12 C9 C25 C24 178.27(18) . . . . ?
C9 C25 C24 C23 -0.4(3) . . . . ?
C25 C24 C23 C15 0.2(3) . . . . ?
C13 C9 C12 C10 -97.24(19) . . . . ?
C25 C9 C12 C10 84.8(2) . . . . ?
N2 C10 C12 C9 55.18(18) . . . . ?
C11 C10 C12 C9 -60.3(2) . . . . ?
C14 C10 C12 C9 -179.43(13) . . . . ?
C14 O4 C16 C17 -121.85(16) . . . . ?
C14 O4 C16 C19 112.26(17) . . . . ?
C22 C17 C16 O4 -54.79(18) . . . . ?
C18 C17 C16 O4 70.15(18) . . . . ?
C22 C17 C16 C19 63.3(2) . . . . ?
C18 C17 C16 C19 -171.73(16) . . . . ?
C26 O5 C15 C23 -8.9(3) . . . . ?
C26 O5 C15 C13 172.87(16) . . . . ?
C24 C23 C15 O5 -178.07(17) . . . . ?
C24 C23 C15 C13 0.1(3) . . . . ?
C9 C13 C15 O5 178.12(17) . . . . ?
C9 C13 C15 C23 -0.2(3) . . . . ?
O4 C16 C19 C21 -64.9(2) . . . . ?
C17 C16 C19 C21 177.05(17) . . . . ?
O4 C16 C19 C20 172.93(19) . . . . ?
C17 C16 C19 C20 54.9(3) . . . . ?
C10 N2 C8 N1 1.87(18) . . . . ?
C10 N2 C8 S1 -177.04(12) . . . . ?
C11 N1 C8 N2 -0.66(18) . . . . ?
C1 N1 C8 N2 -174.57(14) . . . . ?
C11 N1 C8 S1 178.25(12) . . . . ?
C1 N1 C8 S1 4.3(2) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.032



####################################################################### 
# 
# 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_t_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2408297'
loop_
_audit_author_name
_audit_author_address
'Wenya Zheng'
;Xinjiang Normal University
China
;
_audit_update_record             
;
2024-12-06 deposited with the CCDC.	2025-04-08 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         'C18 H15 F N2 O3 S, H2 O'
_chemical_formula_sum            'C18 H17 F N2 O4 S'
_chemical_formula_weight         376.39

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.6102(2)
_cell_length_b                   8.93820(10)
_cell_length_c                   22.5649(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1736.59(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16541
_cell_measurement_theta_min      3.9030
_cell_measurement_theta_max      75.9840

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.995
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75486
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19575
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.918
_diffrn_reflns_theta_max         76.150
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3602
_reflns_number_gt                3581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.999

_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)+(0.0338P)²+0.3465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3602
_refine_ls_number_parameters     243
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_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
O26 O 0.41217(13) 0.20184(15) 0.68797(5) 0.0217(2) Uani 1 1 d D . . . .
H26A H 0.406(3) 0.197(3) 0.7264(8) 0.033 Uiso 1 1 d D U . . .
H26B H 0.507(2) 0.190(3) 0.6780(10) 0.033 Uiso 1 1 d D U . . .
C14 C 1.03282(17) 0.18471(17) 0.72479(7) 0.0161(3) Uani 1 1 d . U . . .
C13 C 0.5948(2) 0.33332(18) 0.82719(8) 0.0237(4) Uani 1 1 d . . . . .
H13 H 0.560072 0.427976 0.841000 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7085(2) 0.32561(18) 0.78380(7) 0.0217(3) Uani 1 1 d . . . . .
H12 H 0.751885 0.414466 0.767684 0.026 Uiso 1 1 calc R U . . .
C11 C 0.75810(16) 0.18655(19) 0.76422(6) 0.0165(3) Uani 1 1 d . . . . .
C15 C 0.53136(17) 0.2026(2) 0.85063(7) 0.0189(3) Uani 1 1 d . . . . .
C17 C 0.69482(19) 0.05684(18) 0.78666(7) 0.0195(3) Uani 1 1 d . . . . .
H17 H 0.729312 -0.037475 0.772389 0.023 Uiso 1 1 calc R U . . .
C16 C 0.5801(2) 0.06359(19) 0.83032(7) 0.0202(3) Uani 1 1 d . . . . .
H16 H 0.536081 -0.025557 0.845916 0.024 Uiso 1 1 calc R U . . .
C10 C 0.83225(19) 0.1581(2) 0.65875(7) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.93982(18) 0.2320(2) 0.51840(7) 0.0221(3) Uani 1 1 d . . . . .
C3 C 0.98450(17) 0.14966(19) 0.62363(7) 0.0180(3) Uani 1 1 d . . . . .
O3 O 0.42089(14) 0.22352(14) 0.89338(5) 0.0253(3) Uani 1 1 d . . . . .
C2 C 1.0047(2) -0.0044(2) 0.59417(7) 0.0216(3) Uani 1 1 d . . . . .
H2A H 1.110978 -0.013033 0.577793 0.026 Uiso 1 1 calc R U . . .
H2B H 0.990666 -0.084150 0.624130 0.026 Uiso 1 1 calc R U . . .
O2 O 0.70138(14) 0.15019(16) 0.63907(5) 0.0276(3) Uani 1 1 d . . . . .
N2 N 1.09633(15) 0.17383(16) 0.67094(6) 0.0187(3) Uani 1 1 d . . . . .
H2 H 1.196950 0.180695 0.664665 0.022 Uiso 1 1 calc R U . . .
C4 C 0.98787(18) 0.26910(19) 0.57596(7) 0.0191(3) Uani 1 1 d . . . . .
C5 C 1.0383(2) 0.4145(2) 0.58809(8) 0.0228(4) Uani 1 1 d . . . . .
H5 H 1.071595 0.441472 0.626777 0.027 Uiso 1 1 calc R U . . .
C1 C 0.8870(2) -0.0241(2) 0.54495(7) 0.0252(4) Uani 1 1 d . . . . .
H1A H 0.904319 -0.122048 0.525585 0.030 Uiso 1 1 calc R U . . .
H1B H 0.781396 -0.024859 0.562262 0.030 Uiso 1 1 calc R U . . .
F1 F 1.09102(16) 0.65859(13) 0.55468(6) 0.0412(3) Uani 1 1 d . . . . .
O1 O 0.89596(16) 0.09211(15) 0.50100(5) 0.0280(3) Uani 1 1 d . . . . .
N1 N 0.87150(15) 0.17710(15) 0.71745(6) 0.0172(3) Uani 1 1 d . . . . .
S1 S 1.12348(4) 0.20313(5) 0.78902(2) 0.01969(10) Uani 1 1 d . U . . .
C6 C 1.0387(2) 0.5178(2) 0.54299(9) 0.0281(4) Uani 1 1 d . . . . .
C7 C 0.9888(2) 0.4855(2) 0.48633(8) 0.0303(4) Uani 1 1 d . . . . .
H7 H 0.988127 0.560249 0.456399 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9397(2) 0.3411(2) 0.47429(8) 0.0290(4) Uani 1 1 d . . . . .
H8 H 0.905628 0.316199 0.435490 0.035 Uiso 1 1 calc R U . . .
C18 C 0.3461(2) 0.0938(2) 0.91657(8) 0.0270(4) Uani 1 1 d . . . . .
H18A H 0.289511 0.042900 0.884736 0.040 Uiso 1 1 calc R U . . .
H18B H 0.273096 0.123508 0.947753 0.040 Uiso 1 1 calc R U . . .
H18C H 0.424191 0.025974 0.933150 0.040 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
C14 N2 1.3361(19) . ?
C14 N1 1.4004(19) . ?
C14 S1 1.6544(15) . ?
C13 C12 1.386(2) . ?
C13 C15 1.394(2) . ?
C12 C11 1.386(2) . ?
C11 C17 1.378(2) . ?
C11 N1 1.4402(18) . ?
C15 O3 1.3674(19) . ?
C15 C16 1.390(2) . ?
C17 C16 1.396(2) . ?
C10 O2 1.213(2) . ?
C10 N1 1.3774(19) . ?
C10 C3 1.534(2) . ?
C9 O1 1.364(2) . ?
C9 C8 1.394(2) . ?
C9 C4 1.403(2) . ?
C3 N2 1.454(2) . ?
C3 C4 1.516(2) . ?
C3 C2 1.539(2) . ?
O3 C18 1.426(2) . ?
C2 C1 1.513(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.374(3) . ?
C1 O1 1.438(2) . ?
F1 C6 1.362(2) . ?
C6 C7 1.379(3) . ?
C7 C8 1.385(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
N2 C14 N1 107.15(13) . . ?
N2 C14 S1 127.65(12) . . ?
N1 C14 S1 125.20(11) . . ?
C12 C13 C15 120.21(15) . . ?
C13 C12 C11 119.15(15) . . ?
C17 C11 C12 121.04(14) . . ?
C17 C11 N1 119.22(14) . . ?
C12 C11 N1 119.66(14) . . ?
O3 C15 C16 124.40(15) . . ?
O3 C15 C13 115.21(15) . . ?
C16 C15 C13 120.39(14) . . ?
C11 C17 C16 120.18(15) . . ?
C15 C16 C17 119.02(15) . . ?
O2 C10 N1 125.96(14) . . ?
O2 C10 C3 126.99(14) . . ?
N1 C10 C3 107.05(13) . . ?
O1 C9 C8 115.84(15) . . ?
O1 C9 C4 124.40(15) . . ?
C8 C9 C4 119.72(16) . . ?
N2 C3 C4 113.81(13) . . ?
N2 C3 C10 100.33(12) . . ?
C4 C3 C10 110.38(13) . . ?
N2 C3 C2 112.05(13) . . ?
C4 C3 C2 108.75(13) . . ?
C10 C3 C2 111.35(14) . . ?
C15 O3 C18 117.53(14) . . ?
C1 C2 C3 110.21(14) . . ?
C14 N2 C3 114.05(12) . . ?
C5 C4 C9 119.53(15) . . ?
C5 C4 C3 121.48(15) . . ?
C9 C4 C3 119.00(15) . . ?
C6 C5 C4 118.73(16) . . ?
O1 C1 C2 112.73(14) . . ?
C9 O1 C1 118.57(13) . . ?
C10 N1 C14 111.29(13) . . ?
C10 N1 C11 123.06(13) . . ?
C14 N1 C11 125.65(12) . . ?
F1 C6 C5 118.55(17) . . ?
F1 C6 C7 118.41(17) . . ?
C5 C6 C7 123.04(18) . . ?
C6 C7 C8 118.16(17) . . ?
C7 C8 C9 120.80(17) . . ?

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
C15 C13 C12 C11 -0.1(3) . . . . ?
C13 C12 C11 C17 0.8(2) . . . . ?
C13 C12 C11 N1 177.46(15) . . . . ?
C12 C13 C15 O3 179.63(15) . . . . ?
C12 C13 C15 C16 -0.7(2) . . . . ?
C12 C11 C17 C16 -0.8(2) . . . . ?
N1 C11 C17 C16 -177.40(15) . . . . ?
O3 C15 C16 C17 -179.59(16) . . . . ?
C13 C15 C16 C17 0.8(2) . . . . ?
C11 C17 C16 C15 0.0(2) . . . . ?
O2 C10 C3 N2 177.14(18) . . . . ?
N1 C10 C3 N2 -2.70(17) . . . . ?
O2 C10 C3 C4 56.8(2) . . . . ?
N1 C10 C3 C4 -123.06(14) . . . . ?
O2 C10 C3 C2 -64.1(2) . . . . ?
N1 C10 C3 C2 116.05(15) . . . . ?
C16 C15 O3 C18 -3.0(2) . . . . ?
C13 C15 O3 C18 176.67(15) . . . . ?
N2 C3 C2 C1 -179.51(13) . . . . ?
C4 C3 C2 C1 -52.82(17) . . . . ?
C10 C3 C2 C1 69.02(17) . . . . ?
N1 C14 N2 C3 -3.29(19) . . . . ?
S1 C14 N2 C3 176.49(12) . . . . ?
C4 C3 N2 C14 121.57(15) . . . . ?
C10 C3 N2 C14 3.71(18) . . . . ?
C2 C3 N2 C14 -114.52(15) . . . . ?
O1 C9 C4 C5 176.58(15) . . . . ?
C8 C9 C4 C5 -1.3(2) . . . . ?
O1 C9 C4 C3 -3.1(2) . . . . ?
C8 C9 C4 C3 178.93(14) . . . . ?
N2 C3 C4 C5 -26.5(2) . . . . ?
C10 C3 C4 C5 85.43(18) . . . . ?
C2 C3 C4 C5 -152.14(15) . . . . ?
N2 C3 C4 C9 153.26(15) . . . . ?
C10 C3 C4 C9 -94.84(17) . . . . ?
C2 C3 C4 C9 27.59(19) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C3 C4 C5 C6 179.97(15) . . . . ?
C3 C2 C1 O1 56.67(19) . . . . ?
C8 C9 O1 C1 -177.32(15) . . . . ?
C4 C9 O1 C1 4.7(2) . . . . ?
C2 C1 O1 C9 -31.9(2) . . . . ?
O2 C10 N1 C14 -178.79(18) . . . . ?
C3 C10 N1 C14 1.05(18) . . . . ?
O2 C10 N1 C11 1.5(3) . . . . ?
C3 C10 N1 C11 -178.61(14) . . . . ?
N2 C14 N1 C10 1.27(18) . . . . ?
S1 C14 N1 C10 -178.53(12) . . . . ?
N2 C14 N1 C11 -179.08(15) . . . . ?
S1 C14 N1 C11 1.1(2) . . . . ?
C17 C11 N1 C10 81.1(2) . . . . ?
C12 C11 N1 C10 -95.61(19) . . . . ?
C17 C11 N1 C14 -98.53(18) . . . . ?
C12 C11 N1 C14 84.8(2) . . . . ?
C4 C5 C6 F1 -178.62(16) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
F1 C6 C7 C8 178.26(17) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
O1 C9 C8 C7 -177.11(16) . . . . ?
C4 C9 C8 C7 1.0(3) . . . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.032



