# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 
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data_GS_GA_43_reduced1_a
_database_code_depnum_ccdc_archive 'CCDC 2323442'
_audit_update_record             
;
2024-01-04 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H33 N O7 S'
_chemical_formula_sum            'C41 H33 N O7 S'
_chemical_formula_weight         683.74

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'

_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                   9.1592(3)
_cell_length_b                   17.6405(5)
_cell_length_c                   10.2784(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.1920(10)
_cell_angle_gamma                90
_cell_volume                     1656.27(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6959
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      20.04

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48772
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         25.140
_diffrn_reflns_theta_full        25.140
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5903
_reflns_number_gt                5025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0411P)²+0.1247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5903
_refine_ls_number_parameters     452
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_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 0.97889(9) 0.25740(5) 0.37254(9) 0.0244(2) Uani 1 1 d . . . . .
O1 O 0.6107(3) 0.69275(13) 0.2586(2) 0.0261(6) Uani 1 1 d . . . . .
O2 O 0.3726(2) 0.57222(13) 0.2678(2) 0.0243(6) Uani 1 1 d . . . . .
O3 O 0.5950(3) 0.62602(14) 0.0698(2) 0.0270(6) Uani 1 1 d . . . . .
O4 O 0.8351(3) 0.34272(13) 0.1650(2) 0.0248(6) Uani 1 1 d . . . . .
O5 O 0.4805(3) 0.51786(14) 0.4477(2) 0.0271(6) Uani 1 1 d . . . . .
O6 O 1.0208(3) 0.23976(13) 0.5062(2) 0.0315(6) Uani 1 1 d . . . . .
O7 O 1.0737(2) 0.23764(13) 0.2742(2) 0.0318(6) Uani 1 1 d . . . . .
N1 N 0.9514(3) 0.35383(16) 0.3690(3) 0.0210(6) Uani 1 1 d . . . . .
C1 C 0.4659(4) 0.80648(19) 0.2124(3) 0.0239(8) Uani 1 1 d . . . . .
C2 C 0.4502(4) 0.8399(2) 0.3333(3) 0.0289(8) Uani 1 1 d . . . . .
H2 H 0.525242 0.834068 0.401298 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3266(4) 0.8815(2) 0.3554(4) 0.0321(9) Uani 1 1 d . . . . .
H3 H 0.317534 0.904633 0.437873 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2165(4) 0.8894(2) 0.2574(3) 0.0304(9) Uani 1 1 d . . . . .
H4 H 0.130450 0.917131 0.272824 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2317(4) 0.8570(2) 0.1368(4) 0.0331(9) Uani 1 1 d . . . . .
H5 H 0.156647 0.863133 0.068742 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3553(4) 0.8157(2) 0.1147(4) 0.0295(9) Uani 1 1 d . . . . .
H6 H 0.364541 0.793306 0.031668 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6028(4) 0.76420(19) 0.1868(4) 0.0283(8) Uani 1 1 d . . . . .
H7A H 0.604122 0.753877 0.092197 0.034 Uiso 1 1 calc R U . . .
H7B H 0.689259 0.795699 0.213666 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6091(4) 0.62878(19) 0.1868(4) 0.0221(8) Uani 1 1 d . . . . .
C9 C 0.6291(4) 0.56075(18) 0.2770(3) 0.0197(8) Uani 1 1 d . . . . .
C10 C 0.6658(4) 0.48654(18) 0.1992(3) 0.0201(8) Uani 1 1 d . . . . .
H10 H 0.709276 0.502191 0.116884 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7849(4) 0.45188(19) 0.2884(3) 0.0192(7) Uani 1 1 d . . . . .
C12 C 0.8333(4) 0.49704(18) 0.3871(3) 0.0190(7) Uani 1 1 d . . . . .
C13 C 0.7570(4) 0.57223(19) 0.3820(3) 0.0211(8) Uani 1 1 d . . . . .
H13A H 0.823366 0.613031 0.356432 0.025 Uiso 1 1 calc R U . . .
H13B H 0.720106 0.585009 0.467457 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4874(4) 0.54793(19) 0.3438(3) 0.0214(8) Uani 1 1 d . . . . .
C15 C 0.2282(4) 0.5554(2) 0.3119(4) 0.0323(9) Uani 1 1 d . . . . .
H15A H 0.216179 0.579814 0.397247 0.039 Uiso 1 1 calc R U . . .
H15B H 0.215102 0.500060 0.321348 0.039 Uiso 1 1 calc R U . . .
C16 C 0.1195(4) 0.5863(2) 0.2103(3) 0.0253(8) Uani 1 1 d . . . . .
C17 C 0.0540(4) 0.5396(2) 0.1140(4) 0.0355(10) Uani 1 1 d . . . . .
H17 H 0.074696 0.486849 0.115304 0.043 Uiso 1 1 calc R U . . .
C18 C -0.0413(4) 0.5695(3) 0.0159(4) 0.0423(11) Uani 1 1 d . . . . .
H18 H -0.085012 0.537302 -0.050115 0.051 Uiso 1 1 calc R U . . .
C19 C -0.0722(4) 0.6459(3) 0.0146(4) 0.0418(11) Uani 1 1 d . . . . .
H19 H -0.136728 0.666410 -0.052984 0.050 Uiso 1 1 calc R U . . .
C20 C -0.0103(4) 0.6929(3) 0.1103(4) 0.0426(11) Uani 1 1 d . . . . .
H20 H -0.033145 0.745391 0.109764 0.051 Uiso 1 1 calc R U . . .
C21 C 0.0854(4) 0.6630(2) 0.2075(4) 0.0368(10) Uani 1 1 d . . . . .
H21 H 0.128432 0.695458 0.273267 0.044 Uiso 1 1 calc R U . . .
C22 C 0.5343(4) 0.43656(19) 0.1631(3) 0.0213(8) Uani 1 1 d . . . . .
C23 C 0.4483(4) 0.4503(2) 0.0484(3) 0.0258(8) Uani 1 1 d . . . . .
H23 H 0.476519 0.488308 -0.010220 0.031 Uiso 1 1 calc R U . . .
C24 C 0.3213(4) 0.4089(2) 0.0192(4) 0.0308(9) Uani 1 1 d . . . . .
H24 H 0.262850 0.418937 -0.059083 0.037 Uiso 1 1 calc R U . . .
C25 C 0.2792(4) 0.3530(2) 0.1032(4) 0.0322(9) Uani 1 1 d . . . . .
H25 H 0.191446 0.325233 0.083803 0.039 Uiso 1 1 calc R U . . .
C26 C 0.3663(4) 0.3382(2) 0.2158(4) 0.0308(9) Uani 1 1 d . . . . .
H26 H 0.339704 0.298979 0.272746 0.037 Uiso 1 1 calc R U . . .
C27 C 0.4916(4) 0.37985(19) 0.2463(3) 0.0254(8) Uani 1 1 d . . . . .
H27 H 0.549354 0.369703 0.324971 0.030 Uiso 1 1 calc R U . . .
C28 C 0.8558(4) 0.38082(19) 0.2635(3) 0.0209(8) Uani 1 1 d . . . . .
C29 C 1.0156(4) 0.40340(19) 0.4667(3) 0.0198(8) Uani 1 1 d . . . . .
C30 C 0.9528(4) 0.47585(19) 0.4774(3) 0.0191(7) Uani 1 1 d . . . . .
C31 C 0.8043(4) 0.21996(19) 0.3347(3) 0.0229(8) Uani 1 1 d . . . . .
C32 C 0.7681(4) 0.1888(2) 0.2129(3) 0.0238(8) Uani 1 1 d . . . . .
H32 H 0.835148 0.190954 0.146723 0.029 Uiso 1 1 calc R U . . .
C33 C 0.6330(4) 0.15437(19) 0.1891(4) 0.0251(8) Uani 1 1 d . . . . .
H33 H 0.607696 0.132907 0.105682 0.030 Uiso 1 1 calc R U . . .
C34 C 0.5336(4) 0.15064(19) 0.2849(4) 0.0261(9) Uani 1 1 d . . . . .
C35 C 0.5720(4) 0.1838(2) 0.4056(4) 0.0270(8) Uani 1 1 d . . . . .
H35 H 0.504169 0.182849 0.471275 0.032 Uiso 1 1 calc R U . . .
C36 C 0.7070(4) 0.21806(19) 0.4318(3) 0.0254(8) Uani 1 1 d . . . . .
H36 H 0.732482 0.239882 0.514861 0.030 Uiso 1 1 calc R U . . .
C37 C 1.1415(4) 0.3849(2) 0.5449(3) 0.0254(8) Uani 1 1 d . . . . .
H37 H 1.187621 0.337156 0.535293 0.030 Uiso 1 1 calc R U . . .
C38 C 1.1984(4) 0.4360(2) 0.6359(4) 0.0280(9) Uani 1 1 d . . . . .
H38 H 1.284217 0.422971 0.688605 0.034 Uiso 1 1 calc R U . . .
C39 C 1.1341(4) 0.5061(2) 0.6528(3) 0.0272(9) Uani 1 1 d . . . . .
H39 H 1.173128 0.539839 0.718479 0.033 Uiso 1 1 calc R U . . .
C40 C 1.0125(4) 0.5262(2) 0.5728(3) 0.0230(8) Uani 1 1 d . . . . .
H40 H 0.968785 0.574517 0.582415 0.028 Uiso 1 1 calc R U . . .
C41 C 0.3900(4) 0.1101(2) 0.2601(4) 0.0318(9) Uani 1 1 d . . . . .
H41A H 0.310443 0.142897 0.285298 0.048 Uiso 1 1 calc R U . . .
H41B H 0.391269 0.063343 0.311545 0.048 Uiso 1 1 calc R U . . .
H41C H 0.374657 0.097710 0.167126 0.048 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 O7 1.423(3) . ?
S1 O6 1.433(2) . ?
S1 N1 1.720(3) . ?
S1 C31 1.747(3) . ?
O1 C8 1.348(4) . ?
O1 C7 1.460(4) . ?
O2 C14 1.334(4) . ?
O2 C15 1.460(4) . ?
O3 C8 1.200(4) . ?
O4 C28 1.219(4) . ?
O5 C14 1.198(4) . ?
N1 C28 1.424(4) . ?
N1 C29 1.426(4) . ?
C1 C6 1.382(5) . ?
C1 C2 1.392(5) . ?
C1 C7 1.499(5) . ?
C2 C3 1.381(5) . ?
C3 C4 1.379(5) . ?
C4 C5 1.382(5) . ?
C5 C6 1.379(5) . ?
C8 C9 1.520(5) . ?
C9 C14 1.529(5) . ?
C9 C13 1.546(5) . ?
C9 C10 1.583(5) . ?
C10 C11 1.503(5) . ?
C10 C22 1.516(5) . ?
C11 C12 1.339(5) . ?
C11 C28 1.443(5) . ?
C12 C30 1.433(5) . ?
C12 C13 1.498(5) . ?
C15 C16 1.492(5) . ?
C16 C21 1.387(5) . ?
C16 C17 1.390(5) . ?
C17 C18 1.388(6) . ?
C18 C19 1.378(6) . ?
C19 C20 1.376(6) . ?
C20 C21 1.384(5) . ?
C22 C23 1.390(5) . ?
C22 C27 1.391(5) . ?
C23 C24 1.388(5) . ?
C24 C25 1.383(6) . ?
C25 C26 1.382(5) . ?
C26 C27 1.379(5) . ?
C29 C37 1.395(5) . ?
C29 C30 1.409(5) . ?
C30 C40 1.403(5) . ?
C31 C32 1.385(5) . ?
C31 C36 1.386(5) . ?
C32 C33 1.384(5) . ?
C33 C34 1.391(5) . ?
C34 C35 1.393(5) . ?
C34 C41 1.502(5) . ?
C35 C36 1.385(5) . ?
C37 C38 1.375(5) . ?
C38 C39 1.386(5) . ?
C39 C40 1.382(5) . ?

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
O7 S1 O6 119.55(16) . . ?
O7 S1 N1 108.86(14) . . ?
O6 S1 N1 105.28(14) . . ?
O7 S1 C31 110.21(16) . . ?
O6 S1 C31 107.91(16) . . ?
N1 S1 C31 103.82(15) . . ?
C8 O1 C7 116.6(3) . . ?
C14 O2 C15 116.5(3) . . ?
C28 N1 C29 122.0(3) . . ?
C28 N1 S1 115.3(2) . . ?
C29 N1 S1 122.6(2) . . ?
C6 C1 C2 118.7(3) . . ?
C6 C1 C7 120.6(3) . . ?
C2 C1 C7 120.7(3) . . ?
C3 C2 C1 120.8(3) . . ?
C4 C3 C2 119.9(3) . . ?
C3 C4 C5 119.8(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 120.6(3) . . ?
O1 C7 C1 110.6(3) . . ?
O3 C8 O1 125.4(3) . . ?
O3 C8 C9 125.4(3) . . ?
O1 C8 C9 109.3(3) . . ?
C8 C9 C14 108.8(3) . . ?
C8 C9 C13 111.9(3) . . ?
C14 C9 C13 109.3(3) . . ?
C8 C9 C10 111.4(3) . . ?
C14 C9 C10 108.8(3) . . ?
C13 C9 C10 106.4(3) . . ?
C11 C10 C22 116.2(3) . . ?
C11 C10 C9 101.5(3) . . ?
C22 C10 C9 114.3(3) . . ?
C12 C11 C28 121.5(3) . . ?
C12 C11 C10 113.9(3) . . ?
C28 C11 C10 124.1(3) . . ?
C11 C12 C30 122.0(3) . . ?
C11 C12 C13 111.9(3) . . ?
C30 C12 C13 125.9(3) . . ?
C12 C13 C9 103.6(3) . . ?
O5 C14 O2 125.0(3) . . ?
O5 C14 C9 124.6(3) . . ?
O2 C14 C9 110.4(3) . . ?
O2 C15 C16 106.4(3) . . ?
C21 C16 C17 118.6(4) . . ?
C21 C16 C15 120.6(3) . . ?
C17 C16 C15 120.9(3) . . ?
C18 C17 C16 120.5(4) . . ?
C19 C18 C17 119.7(4) . . ?
C20 C19 C18 120.6(4) . . ?
C19 C20 C21 119.5(4) . . ?
C20 C21 C16 121.1(4) . . ?
C23 C22 C27 118.7(3) . . ?
C23 C22 C10 119.8(3) . . ?
C27 C22 C10 121.4(3) . . ?
C24 C23 C22 120.4(3) . . ?
C25 C24 C23 120.5(3) . . ?
C26 C25 C24 119.1(4) . . ?
C27 C26 C25 120.7(4) . . ?
C26 C27 C22 120.6(3) . . ?
O4 C28 N1 119.8(3) . . ?
O4 C28 C11 125.6(3) . . ?
N1 C28 C11 114.5(3) . . ?
C37 C29 C30 119.5(3) . . ?
C37 C29 N1 122.9(3) . . ?
C30 C29 N1 117.5(3) . . ?
C40 C30 C29 119.3(3) . . ?
C40 C30 C12 121.9(3) . . ?
C29 C30 C12 118.9(3) . . ?
C32 C31 C36 121.1(3) . . ?
C32 C31 S1 120.4(3) . . ?
C36 C31 S1 118.4(3) . . ?
C33 C32 C31 119.1(3) . . ?
C32 C33 C34 121.2(3) . . ?
C33 C34 C35 118.4(3) . . ?
C33 C34 C41 120.8(3) . . ?
C35 C34 C41 120.7(3) . . ?
C36 C35 C34 121.3(3) . . ?
C35 C36 C31 118.9(3) . . ?
C38 C37 C29 119.6(3) . . ?
C37 C38 C39 121.9(3) . . ?
C40 C39 C38 119.0(3) . . ?
C39 C40 C30 120.6(3) . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.043



