# Supplementary Information (SI) for Green 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_240613_yly_1
_database_code_depnum_ccdc_archive 'CCDC 2371496'
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_audit_creation_date             2024-06-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N2 O5 S, C2 H6 O S'
_chemical_formula_sum            'C22 H22 N2 O6 S2'
_chemical_formula_weight         474.53
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   13.8810(5)
_cell_length_b                   11.8967(4)
_cell_length_c                   14.0748(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.8250(10)
_cell_angle_gamma                90
_cell_volume                     2172.44(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      28.273
_cell_measurement_theta_min      2.308
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24965
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.308
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4312
_reflns_number_total             5350
_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       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.121
_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)+(0.0231P)²+1.9825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.30409(4) 0.54027(4) 0.56472(4) 0.02816(12) Uani 1 1 d . . . . .
O1 O 0.48676(12) 1.09569(12) 0.65578(11) 0.0340(3) Uani 1 1 d . . . . .
N1 N 0.56479(13) 0.78291(14) 0.57335(14) 0.0304(4) Uani 1 1 d . . . . .
C1 C 0.66119(19) 1.1497(2) 0.72103(17) 0.0389(5) Uani 1 1 d . . . . .
H1 H 0.640055 1.221886 0.734892 0.047 Uiso 1 1 calc R U . . .
O2 O 0.32281(12) 1.05359(13) 0.60674(13) 0.0414(4) Uani 1 1 d . . . . .
N2 N 0.25428(13) 0.85339(16) 0.52155(14) 0.0344(4) Uani 1 1 d . . . . .
H2A H 0.206408 0.803017 0.492582 0.041 Uiso 1 1 calc R U . . .
H2B H 0.237033 0.919104 0.539410 0.041 Uiso 1 1 calc R U . . .
C2 C 0.76416(19) 1.1253(2) 0.74524(18) 0.0429(6) Uani 1 1 d . . . . .
H2 H 0.814571 1.180870 0.776775 0.051 Uiso 1 1 calc R U . . .
O3 O 0.26358(12) 0.60584(13) 0.62858(11) 0.0374(4) Uani 1 1 d . . . . .
C3 C 0.79491(18) 1.0198(2) 0.72382(18) 0.0404(6) Uani 1 1 d . . . . .
H3 H 0.866073 1.003398 0.740987 0.048 Uiso 1 1 calc R U . . .
O4 O 0.40325(11) 0.48719(13) 0.61177(12) 0.0381(4) Uani 1 1 d . . . . .
C4 C 0.72191(17) 0.9391(2) 0.67766(16) 0.0341(5) Uani 1 1 d . . . . .
H4 H 0.743157 0.867304 0.663011 0.041 Uiso 1 1 calc R U . . .
O5 O 0.00457(11) 0.18649(12) 0.36689(12) 0.0347(3) Uani 1 1 d . . . . .
C5 C 0.61667(16) 0.96205(17) 0.65215(15) 0.0276(4) Uani 1 1 d . . . . .
C6 C 0.58891(17) 1.06708(18) 0.67608(15) 0.0304(5) Uani 1 1 d . . . . .
C7 C 0.40825(17) 1.02052(18) 0.61444(16) 0.0309(5) Uani 1 1 d . . . . .
C8 C 0.43282(15) 0.90991(16) 0.58483(15) 0.0262(4) Uani 1 1 d . . . . .
C9 C 0.53615(15) 0.88079(17) 0.60172(15) 0.0262(4) Uani 1 1 d . . . . .
C10 C 0.48875(16) 0.70939(18) 0.52907(16) 0.0305(4) Uani 1 1 d . . . . .
H10 H 0.507983 0.639682 0.508061 0.037 Uiso 1 1 calc R U . . .
C11 C 0.38516(16) 0.72533(17) 0.51107(15) 0.0272(4) Uani 1 1 d . . . . .
C12 C 0.35334(15) 0.83007(17) 0.53845(15) 0.0268(4) Uani 1 1 d . . . . .
C13 C 0.31121(16) 0.63082(17) 0.46540(15) 0.0290(4) Uani 1 1 d . . . . .
H13A H 0.334900 0.587478 0.417768 0.035 Uiso 1 1 calc R U . . .
H13B H 0.242070 0.661689 0.426856 0.035 Uiso 1 1 calc R U . . .
C14 C 0.21341(15) 0.43651(17) 0.50288(15) 0.0262(4) Uani 1 1 d . . . . .
C15 C 0.24415(16) 0.32465(17) 0.50655(15) 0.0274(4) Uani 1 1 d . . . . .
H15 H 0.314485 0.304630 0.539363 0.033 Uiso 1 1 calc R U . . .
C16 C 0.17127(16) 0.24328(17) 0.46197(16) 0.0289(4) Uani 1 1 d . . . . .
H16 H 0.191120 0.166497 0.465914 0.035 Uiso 1 1 calc R U . . .
C17 C 0.06831(16) 0.27325(17) 0.41101(15) 0.0270(4) Uani 1 1 d . . . . .
C18 C 0.03762(16) 0.38503(17) 0.40845(16) 0.0286(4) Uani 1 1 d . . . . .
H18 H -0.032604 0.405191 0.375149 0.034 Uiso 1 1 calc R U . . .
C19 C 0.11024(16) 0.46632(17) 0.45481(16) 0.0290(4) Uani 1 1 d . . . . .
H19 H 0.089860 0.542663 0.453932 0.035 Uiso 1 1 calc R U . . .
C20 C -0.10191(17) 0.2125(2) 0.31138(19) 0.0394(5) Uani 1 1 d . . . . .
H20A H -0.106547 0.265839 0.256844 0.059 Uiso 1 1 calc R U . . .
H20B H -0.132681 0.246026 0.357532 0.059 Uiso 1 1 calc R U . . .
H20C H -0.139038 0.143469 0.281959 0.059 Uiso 1 1 calc R U . . .
S2 S 0.48942(4) 0.71834(5) 0.81056(4) 0.03397(14) Uani 1 1 d . . . . .
O6 O 0.57836(13) 0.76793(15) 0.89592(17) 0.0604(6) Uani 1 1 d . . . . .
C21 C 0.38223(16) 0.8064(2) 0.80014(17) 0.0347(5) Uani 1 1 d . . . . .
H21A H 0.373130 0.810095 0.865998 0.052 Uiso 1 1 calc R U . . .
H21B H 0.319833 0.775336 0.749070 0.052 Uiso 1 1 calc R U . . .
H21C H 0.394786 0.882051 0.779620 0.052 Uiso 1 1 calc R U . . .
C22 C 0.4501(2) 0.5983(2) 0.8630(2) 0.0458(6) Uani 1 1 d . . . . .
H22A H 0.499396 0.537003 0.870199 0.069 Uiso 1 1 calc R U . . .
H22B H 0.381517 0.574419 0.817877 0.069 Uiso 1 1 calc R U . . .
H22C H 0.447735 0.617248 0.929930 0.069 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
S1 O3 1.4464(15) . ?
S1 O4 1.4434(16) . ?
S1 C13 1.795(2) . ?
S1 C14 1.757(2) . ?
O1 C6 1.386(3) . ?
O1 C7 1.369(3) . ?
N1 C9 1.336(3) . ?
N1 C10 1.342(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.377(3) . ?
C1 C6 1.386(3) . ?
O2 C7 1.217(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C12 1.339(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(3) . ?
O5 C17 1.358(2) . ?
O5 C20 1.439(3) . ?
C5 C6 1.384(3) . ?
C5 C9 1.457(3) . ?
C7 C8 1.457(3) . ?
C8 C9 1.411(3) . ?
C8 C12 1.426(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 C12 1.420(3) . ?
C11 C13 1.504(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.393(3) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(3) . ?
C17 C18 1.393(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
S2 O6 1.5036(18) . ?
S2 C21 1.782(2) . ?
S2 C22 1.781(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 C13 107.54(10) . . ?
O3 S1 C14 108.57(9) . . ?
O4 S1 O3 117.96(10) . . ?
O4 S1 C13 108.19(10) . . ?
O4 S1 C14 108.56(10) . . ?
C14 S1 C13 105.30(9) . . ?
C7 O1 C6 121.92(16) . . ?
C9 N1 C10 116.00(18) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.9(2) . . ?
C6 C1 H1 120.6 . . ?
H2A N2 H2B 120.0 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C17 O5 C20 117.48(16) . . ?
C4 C5 C9 123.00(19) . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 C9 119.07(19) . . ?
O1 C6 C1 116.20(19) . . ?
C5 C6 O1 121.64(19) . . ?
C5 C6 C1 122.2(2) . . ?
O1 C7 C8 118.65(18) . . ?
O2 C7 O1 115.46(19) . . ?
O2 C7 C8 125.9(2) . . ?
C9 C8 C7 120.06(19) . . ?
C9 C8 C12 119.22(18) . . ?
C12 C8 C7 120.72(18) . . ?
N1 C9 C5 117.74(18) . . ?
N1 C9 C8 123.79(19) . . ?
C8 C9 C5 118.47(18) . . ?
N1 C10 H10 116.9 . . ?
N1 C10 C11 126.25(19) . . ?
C11 C10 H10 116.9 . . ?
C10 C11 C12 118.33(19) . . ?
C10 C11 C13 118.91(19) . . ?
C12 C11 C13 122.75(18) . . ?
N2 C12 C8 121.46(19) . . ?
N2 C12 C11 122.18(19) . . ?
C11 C12 C8 116.36(18) . . ?
S1 C13 H13A 109.8 . . ?
S1 C13 H13B 109.8 . . ?
C11 C13 S1 109.51(14) . . ?
C11 C13 H13A 109.8 . . ?
C11 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 S1 119.79(16) . . ?
C15 C14 C19 120.61(19) . . ?
C19 C14 S1 119.53(15) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.21(19) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.33(19) . . ?
C17 C16 H16 119.8 . . ?
O5 C17 C16 114.95(17) . . ?
O5 C17 C18 124.77(19) . . ?
C18 C17 C16 120.28(19) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.40(19) . . ?
C19 C18 H18 120.3 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.12(19) . . ?
C18 C19 H19 119.9 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 S2 C21 105.04(11) . . ?
O6 S2 C22 105.61(12) . . ?
C22 S2 C21 97.78(12) . . ?
S2 C21 H21A 109.5 . . ?
S2 C21 H21B 109.5 . . ?
S2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S2 C22 H22A 109.5 . . ?
S2 C22 H22B 109.5 . . ?
S2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
