# Supplementary Information (SI) for Chemical Science.
# 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_s1
_database_code_depnum_ccdc_archive 'CCDC 2472077'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2025-07-12 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-07-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N3 O6 S, H2 O'
_chemical_formula_sum            'C21 H23 N3 O7 S'
_chemical_formula_weight         461.48
_chemical_absolute_configuration ad
_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'
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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.0199(2)
_cell_length_b                   16.2513(5)
_cell_length_c                   18.7458(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2138.57(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9749
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      31.36
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            105722
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.463
_diffrn_reflns_theta_min         2.509
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon II CMOS area detector'
_diffrn_measurement_method       'shutterless omega and phi scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IMuS microfocus Mo tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6506
_reflns_number_total             7072
_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       'Bruker Apex4 V.2022.1-1/SAINT V8.40B'
_computing_data_collection       'Bruker Apex4 V.2022.1-1'
_computing_data_reduction        'Bruker Apex4 V.2022.1-1/SAINT V8.40B'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 2760 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         7072
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.109
_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)+(0.0409P)²+0.6991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0908
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C16(H16), C17(H17), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 -0.14606(6) 0.81705(3) 0.94690(2) 0.01952(9) Uani 1 1 d . . . . .
O1 O -0.0658(2) 0.83586(10) 1.01479(7) 0.0284(3) Uani 1 1 d . . . . .
O1W O 0.8246(3) 0.7882(2) 0.59709(14) 0.0745(10) Uani 1 1 d . . . . .
H1WA H 0.730(9) 0.784(4) 0.618(3) 0.112 Uiso 1 1 d R . . . .
H1WB H 0.802(8) 0.813(3) 0.560(3) 0.112 Uiso 1 1 d R . . . .
H2 H 0.069(7) 0.741(3) 0.622(2) 0.089 Uiso 1 1 d R . . . .
H3A H 0.460(7) 0.528(3) 0.651(3) 0.089 Uiso 1 1 d R . . . .
H3B H 0.483(7) 0.509(3) 0.570(2) 0.089 Uiso 1 1 d R . . . .
O2 O -0.3331(2) 0.84515(10) 0.93114(8) 0.0315(3) Uani 1 1 d . . . . .
O3 O 0.5133(2) 0.99035(9) 0.74677(8) 0.0282(3) Uani 1 1 d . . . . .
O4 O 0.4777(2) 0.77474(10) 0.66409(9) 0.0297(3) Uani 1 1 d . . . . .
O5 O 0.2913(3) 0.62077(12) 0.52447(8) 0.0416(4) Uani 1 1 d . . . . .
O6 O -0.1421(2) 0.71902(8) 0.94381(7) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.3611(2) 0.93908(9) 0.65065(8) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.1845(2) 0.72991(9) 0.63413(9) 0.0224(3) Uani 1 1 d . . . . .
N3 N 0.4382(4) 0.53956(13) 0.60464(11) 0.0386(5) Uani 1 1 d . . . . .
C1 C 0.0080(3) 0.84831(11) 0.87744(9) 0.0185(3) Uani 1 1 d . . . . .
C2 C -0.0694(3) 0.87711(11) 0.81381(9) 0.0200(3) Uani 1 1 d . . . . .
H2A H -0.203480 0.877494 0.806849 0.024 Uiso 1 1 calc R . . . .
C3 C 0.0518(3) 0.90525(11) 0.76067(9) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.000643 0.924950 0.716979 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2485(3) 0.90471(11) 0.77117(9) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.3226(3) 0.87354(12) 0.83473(10) 0.0221(3) Uani 1 1 d . . . . .
H5 H 0.456686 0.871938 0.841379 0.027 Uiso 1 1 calc R . . . .
C6 C 0.2039(3) 0.84487(12) 0.88835(9) 0.0220(3) Uani 1 1 d . . . . .
H6 H 0.254940 0.823429 0.931438 0.026 Uiso 1 1 calc R . . . .
C7 C 0.3857(3) 0.94664(11) 0.72123(9) 0.0197(3) Uani 1 1 d . . . . .
C8 C 0.4774(3) 0.98798(12) 0.60070(10) 0.0264(4) Uani 1 1 d . . . . .
H8A H 0.610060 0.967484 0.598597 0.032 Uiso 1 1 calc R . . . .
H8B H 0.478267 1.046927 0.614038 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3741(4) 0.97417(12) 0.53051(10) 0.0301(4) Uani 1 1 d . . . . .
H9A H 0.459674 0.983838 0.489374 0.036 Uiso 1 1 calc R . . . .
H9B H 0.261504 1.010522 0.526310 0.036 Uiso 1 1 calc R . . . .
C10 C 0.3152(3) 0.88381(12) 0.53523(9) 0.0262(4) Uani 1 1 d . . . . .
H10A H 0.422799 0.847110 0.522881 0.031 Uiso 1 1 calc R . . . .
H10B H 0.206960 0.871992 0.502956 0.031 Uiso 1 1 calc R . . . .
C11 C 0.2565(3) 0.87304(10) 0.61422(9) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.116046 0.880824 0.619934 0.022 Uiso 1 1 calc R . . . .
C12 C 0.3164(3) 0.78815(11) 0.64086(9) 0.0188(3) Uani 1 1 d . . . . .
C13 C 0.2278(3) 0.64454(11) 0.64964(10) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.316415 0.642558 0.691375 0.026 Uiso 1 1 calc R . . . .
C14 C 0.0438(3) 0.59803(12) 0.66930(10) 0.0247(4) Uani 1 1 d . . . . .
H14A H -0.056851 0.611130 0.634085 0.030 Uiso 1 1 calc R . . . .
H14B H 0.067625 0.538026 0.667505 0.030 Uiso 1 1 calc R . . . .
C15 C -0.0235(3) 0.62153(11) 0.74306(10) 0.0214(3) Uani 1 1 d . . . . .
C16 C 0.0969(3) 0.60761(12) 0.80130(10) 0.0260(4) Uani 1 1 d . . . . .
H16 H 0.210975 0.577057 0.794788 0.031 Uiso 1 1 calc R . . . .
C17 C 0.0521(3) 0.63777(12) 0.86826(10) 0.0262(4) Uani 1 1 d . . . . .
H17 H 0.135050 0.629175 0.907601 0.031 Uiso 1 1 calc R . . . .
C18 C -0.1160(3) 0.68062(12) 0.87640(10) 0.0234(3) Uani 1 1 d . . . . .
C19 C -0.2468(3) 0.68953(13) 0.82208(11) 0.0253(4) Uani 1 1 d . . . . .
H19 H -0.366538 0.715078 0.830315 0.030 Uiso 1 1 calc R . . . .
C20 C -0.1979(3) 0.65980(11) 0.75437(10) 0.0236(3) Uani 1 1 d . . . . .
H20 H -0.284739 0.665847 0.715855 0.028 Uiso 1 1 calc R . . . .
C21 C 0.3234(3) 0.60172(12) 0.58651(10) 0.0263(4) Uani 1 1 d . . . . .


_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 O1 1.4251(15) . ?
S1 O2 1.4212(16) . ?
S1 O6 1.5944(14) . ?
S1 C1 1.7671(18) . ?
O3 C7 1.239(2) . ?
O4 C12 1.233(2) . ?
O5 C21 1.224(2) . ?
O6 C18 1.421(2) . ?
N1 C7 1.340(2) . ?
N1 C8 1.474(2) . ?
N1 C11 1.469(2) . ?
N2 C12 1.330(2) . ?
N2 C13 1.450(2) . ?
N3 C21 1.336(3) . ?
C1 C2 1.392(2) . ?
C1 C6 1.391(3) . ?
C2 C3 1.388(2) . ?
C3 C4 1.394(3) . ?
C4 C5 1.395(2) . ?
C4 C7 1.506(2) . ?
C5 C6 1.386(2) . ?
C8 C9 1.519(3) . ?
C9 C10 1.528(3) . ?
C10 C11 1.547(2) . ?
C11 C12 1.526(2) . ?
C13 C14 1.542(3) . ?
C13 C21 1.528(3) . ?
C14 C15 1.510(3) . ?
C15 C16 1.399(3) . ?
C15 C20 1.390(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.379(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.401(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
O1 S1 O6 103.88(8) . . ?
O1 S1 C1 110.76(9) . . ?
O2 S1 O1 118.82(10) . . ?
O2 S1 O6 109.26(10) . . ?
O2 S1 C1 108.65(9) . . ?
O6 S1 C1 104.46(8) . . ?
C18 O6 S1 118.25(11) . . ?
C7 N1 C8 120.41(16) . . ?
C7 N1 C11 126.19(15) . . ?
C11 N1 C8 112.04(14) . . ?
C12 N2 C13 121.07(16) . . ?
C2 C1 S1 119.29(14) . . ?
C6 C1 S1 119.01(13) . . ?
C6 C1 C2 121.69(16) . . ?
C3 C2 C1 119.11(17) . . ?
C2 C3 C4 120.26(17) . . ?
C3 C4 C5 119.46(16) . . ?
C3 C4 C7 122.88(16) . . ?
C5 C4 C7 117.15(16) . . ?
C6 C5 C4 121.13(17) . . ?
C5 C6 C1 118.30(16) . . ?
O3 C7 N1 121.81(17) . . ?
O3 C7 C4 118.79(16) . . ?
N1 C7 C4 119.32(16) . . ?
N1 C8 C9 101.91(16) . . ?
C8 C9 C10 102.77(15) . . ?
C9 C10 C11 103.67(15) . . ?
N1 C11 C10 103.25(14) . . ?
N1 C11 C12 111.77(14) . . ?
C12 C11 C10 110.02(15) . . ?
O4 C12 N2 123.17(17) . . ?
O4 C12 C11 121.88(16) . . ?
N2 C12 C11 114.89(16) . . ?
N2 C13 C14 109.96(16) . . ?
N2 C13 C21 111.88(15) . . ?
C21 C13 C14 109.26(15) . . ?
C15 C14 C13 110.91(15) . . ?
C16 C15 C14 119.00(18) . . ?
C20 C15 C14 121.90(17) . . ?
C20 C15 C16 119.05(17) . . ?
C17 C16 C15 120.88(19) . . ?
C18 C17 C16 118.29(18) . . ?
C17 C18 O6 115.49(17) . . ?
C19 C18 O6 121.67(18) . . ?
C19 C18 C17 122.76(18) . . ?
C18 C19 C20 118.02(18) . . ?
C15 C20 C19 120.57(17) . . ?
O5 C21 N3 122.9(2) . . ?
O5 C21 C13 122.66(19) . . ?
N3 C21 C13 114.34(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
