# Supplementary Information (SI) for Chemical Science.
# 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_DS_277_120K_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2358094'
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-09-10 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         'C31 H27 N O3 S'
_chemical_formula_sum            'C31 H27 N O3 S'
_chemical_formula_weight         493.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.8078(18)
_cell_length_b                   31.102(8)
_cell_length_c                   12.122(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.747(8)
_cell_angle_gamma                90
_cell_volume                     2529.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      31.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.162
_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 D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            94382
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.620
_diffrn_reflns_theta_max         31.542
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8403
_reflns_number_gt                7679
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX4'
_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)+(0.0467P)²+1.2816P] 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_number_reflns         8403
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.006
_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 0.80245(4) 0.34186(2) 0.71216(2) 0.01337(6) Uani 1 1 d . . . . .
O1 O 1.11429(12) 0.44884(3) 0.61283(8) 0.02053(17) Uani 1 1 d . . . . .
O2 O 0.98457(12) 0.35447(3) 0.67712(8) 0.02093(17) Uani 1 1 d . . . . .
O3 O 0.78378(14) 0.34388(3) 0.82824(7) 0.02149(17) Uani 1 1 d . . . . .
N1 N 0.62549(13) 0.37226(3) 0.64354(7) 0.01299(16) Uani 1 1 d . . . . .
C1 C 0.72452(17) 0.52156(4) 0.87563(9) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.92311(17) 0.52589(3) 0.85519(9) 0.0172(2) Uani 1 1 d . . . . .
C3 C 1.0540(2) 0.55511(4) 0.92157(10) 0.0238(2) Uani 1 1 d . . . . .
H3 H 1.185977 0.558737 0.907263 0.029 Uiso 1 1 calc R U . . .
C4 C 0.9923(2) 0.57807(4) 1.00578(11) 0.0283(3) Uani 1 1 d . . . . .
H4 H 1.081372 0.597367 1.049735 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7966(2) 0.57308(4) 1.02724(11) 0.0284(3) Uani 1 1 d . . . . .
H5 H 0.755144 0.588769 1.086516 0.034 Uiso 1 1 calc R U . . .
C6 C 0.6652(2) 0.54585(4) 0.96358(10) 0.0240(2) Uani 1 1 d . . . . .
H6 H 0.533082 0.543211 0.978447 0.029 Uiso 1 1 calc R U . . .
C7 C 0.59338(17) 0.49328(4) 0.80668(10) 0.0180(2) Uani 1 1 d . . . . .
H7 H 0.459883 0.490306 0.818957 0.022 Uiso 1 1 calc R U . . .
C8 C 0.65590(16) 0.47019(3) 0.72271(9) 0.01594(19) Uani 1 1 d . . . . .
H8 H 0.564579 0.452103 0.676150 0.019 Uiso 1 1 calc R U . . .
C9 C 0.85629(15) 0.47314(3) 0.70491(9) 0.01390(18) Uani 1 1 d . . . . .
C10 C 0.98496(16) 0.50084(3) 0.77029(9) 0.01607(19) Uani 1 1 d . . . . .
H10 H 1.118627 0.503116 0.757812 0.019 Uiso 1 1 calc R U . . .
C11 C 0.93597(16) 0.44826(3) 0.61625(9) 0.01451(18) Uani 1 1 d . . . . .
C12 C 0.79540(15) 0.42656(3) 0.52381(9) 0.01339(18) Uani 1 1 d . . . . .
C13 C 0.65253(15) 0.38908(3) 0.53881(9) 0.01275(17) Uani 1 1 d . . . . .
C14 C 0.55484(16) 0.38173(3) 0.43355(9) 0.01454(18) Uani 1 1 d . . . . .
C15 C 0.39177(16) 0.35300(3) 0.38630(9) 0.01466(18) Uani 1 1 d . . . . .
C16 C 0.26005(17) 0.36522(4) 0.28956(9) 0.0181(2) Uani 1 1 d . . . . .
H16 H 0.278973 0.391890 0.254623 0.022 Uiso 1 1 calc R U . . .
C17 C 0.10226(18) 0.33882(4) 0.24418(10) 0.0215(2) Uani 1 1 d . . . . .
H17 H 0.013834 0.347634 0.178904 0.026 Uiso 1 1 calc R U . . .
C18 C 0.07320(18) 0.29963(4) 0.29377(10) 0.0224(2) Uani 1 1 d . . . . .
H18 H -0.035689 0.281782 0.263103 0.027 Uiso 1 1 calc R U . . .
C19 C 0.20436(18) 0.28662(4) 0.38859(10) 0.0204(2) Uani 1 1 d . . . . .
H19 H 0.185936 0.259659 0.422212 0.025 Uiso 1 1 calc R U . . .
C20 C 0.36227(17) 0.31295(4) 0.43430(9) 0.0177(2) Uani 1 1 d . . . . .
H20 H 0.451396 0.303714 0.498870 0.021 Uiso 1 1 calc R U . . .
C21 C 0.87407(17) 0.41055(4) 0.41800(10) 0.0187(2) Uani 1 1 d . . . . .
H21A H 0.925156 0.380692 0.422441 0.022 Uiso 1 1 calc R U . . .
H21B H 0.965170 0.430638 0.388298 0.022 Uiso 1 1 calc R U . . .
C22 C 0.64928(17) 0.41536(4) 0.36563(9) 0.0176(2) Uani 1 1 d . . . . .
H22 H 0.607319 0.417445 0.282663 0.021 Uiso 1 1 calc R U . . .
C23 C 0.64732(17) 0.45583(3) 0.44106(9) 0.0174(2) Uani 1 1 d . . . . .
H23A H 0.518285 0.461953 0.465156 0.021 Uiso 1 1 calc R U . . .
H23B H 0.707654 0.481954 0.414191 0.021 Uiso 1 1 calc R U . . .
C24 C 0.74227(15) 0.28905(3) 0.66689(8) 0.01300(17) Uani 1 1 d . . . . .
C25 C 0.82042(16) 0.27174(4) 0.57737(9) 0.01650(19) Uani 1 1 d . . . . .
H25 H 0.915285 0.287385 0.544265 0.020 Uiso 1 1 calc R U . . .
C26 C 0.75742(18) 0.23124(4) 0.53724(9) 0.0188(2) Uani 1 1 d . . . . .
H26 H 0.811503 0.219080 0.477011 0.023 Uiso 1 1 calc R U . . .
C27 C 0.61589(18) 0.20817(4) 0.58414(10) 0.0195(2) Uani 1 1 d . . . . .
C28 C 0.54025(17) 0.22615(4) 0.67386(10) 0.0185(2) Uani 1 1 d . . . . .
H28 H 0.444455 0.210670 0.706612 0.022 Uiso 1 1 calc R U . . .
C29 C 0.60288(16) 0.26631(3) 0.71592(9) 0.01521(18) Uani 1 1 d . . . . .
H29 H 0.551373 0.278155 0.777398 0.018 Uiso 1 1 calc R U . . .
C30 C 0.42347(16) 0.36786(4) 0.67090(10) 0.0182(2) Uani 1 1 d . . . . .
H30A H 0.335688 0.389566 0.629783 0.027 Uiso 1 1 calc R U . . .
H30B H 0.428824 0.371988 0.751495 0.027 Uiso 1 1 calc R U . . .
H30C H 0.371648 0.339102 0.649584 0.027 Uiso 1 1 calc R U . . .
C31 C 0.5453(3) 0.16449(5) 0.54084(13) 0.0341(3) Uani 1 1 d . . . . .
H31A H 0.586302 0.142860 0.598977 0.051 Uiso 1 1 calc R U . . .
H31B H 0.603949 0.157579 0.474534 0.051 Uiso 1 1 calc R U . . .
H31C H 0.399649 0.164583 0.520827 0.051 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 O2 1.4317(9) . ?
S1 O3 1.4356(9) . ?
S1 N1 1.6425(10) . ?
S1 C24 1.7581(11) . ?
O1 C11 1.2218(13) . ?
N1 C13 1.4136(13) . ?
N1 C30 1.4746(14) . ?
C1 C7 1.4200(16) . ?
C1 C6 1.4203(16) . ?
C1 C2 1.4215(17) . ?
C2 C10 1.4108(16) . ?
C2 C3 1.4231(16) . ?
C3 C4 1.3690(19) . ?
C4 C5 1.409(2) . ?
C5 C6 1.3708(19) . ?
C7 C8 1.3711(15) . ?
C8 C9 1.4197(15) . ?
C9 C10 1.3794(15) . ?
C9 C11 1.4985(15) . ?
C11 C12 1.5045(15) . ?
C12 C13 1.5487(14) . ?
C12 C21 1.5533(15) . ?
C12 C23 1.5840(15) . ?
C12 C22 2.0353(16) . ?
C13 C14 1.3547(15) . ?
C14 C15 1.4643(15) . ?
C14 C22 1.5376(15) . ?
C15 C16 1.4028(15) . ?
C15 C20 1.4035(15) . ?
C16 C17 1.3895(17) . ?
C17 C18 1.3879(18) . ?
C18 C19 1.3909(17) . ?
C19 C20 1.3897(16) . ?
C21 C22 1.5615(17) . ?
C22 C23 1.5573(16) . ?
C24 C29 1.3947(14) . ?
C24 C25 1.3950(15) . ?
C25 C26 1.3919(16) . ?
C26 C27 1.3970(16) . ?
C27 C28 1.3965(16) . ?
C27 C31 1.5058(18) . ?
C28 C29 1.3885(15) . ?

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
O2 S1 O3 120.25(6) . . ?
O2 S1 N1 106.85(5) . . ?
O3 S1 N1 106.98(5) . . ?
O2 S1 C24 109.33(5) . . ?
O3 S1 C24 106.99(5) . . ?
N1 S1 C24 105.52(5) . . ?
C13 N1 C30 120.30(9) . . ?
C13 N1 S1 118.15(7) . . ?
C30 N1 S1 117.69(7) . . ?
C7 C1 C6 122.75(11) . . ?
C7 C1 C2 118.54(10) . . ?
C6 C1 C2 118.70(11) . . ?
C10 C2 C1 119.01(10) . . ?
C10 C2 C3 121.97(11) . . ?
C1 C2 C3 119.02(11) . . ?
C4 C3 C2 120.85(13) . . ?
C3 C4 C5 119.98(12) . . ?
C6 C5 C4 120.77(12) . . ?
C5 C6 C1 120.65(13) . . ?
C8 C7 C1 121.21(10) . . ?
C7 C8 C9 120.40(10) . . ?
C10 C9 C8 119.09(10) . . ?
C10 C9 C11 117.57(10) . . ?
C8 C9 C11 123.33(9) . . ?
C9 C10 C2 121.68(10) . . ?
O1 C11 C9 119.94(10) . . ?
O1 C11 C12 119.45(10) . . ?
C9 C11 C12 120.26(9) . . ?
C11 C12 C13 125.67(9) . . ?
C11 C12 C21 119.61(9) . . ?
C13 C12 C21 99.60(8) . . ?
C11 C12 C23 118.06(9) . . ?
C13 C12 C23 99.32(8) . . ?
C21 C12 C23 86.14(8) . . ?
C11 C12 C22 157.87(8) . . ?
C13 C12 C22 76.42(7) . . ?
C21 C12 C22 49.37(6) . . ?
C23 C12 C22 49.05(6) . . ?
C14 C13 N1 131.74(10) . . ?
C14 C13 C12 103.55(9) . . ?
N1 C13 C12 124.32(9) . . ?
C13 C14 C15 133.64(10) . . ?
C13 C14 C22 101.93(9) . . ?
C15 C14 C22 124.31(9) . . ?
C16 C15 C20 118.10(10) . . ?
C16 C15 C14 119.77(10) . . ?
C20 C15 C14 122.13(10) . . ?
C17 C16 C15 120.84(11) . . ?
C18 C17 C16 120.32(11) . . ?
C17 C18 C19 119.65(11) . . ?
C20 C19 C18 120.21(11) . . ?
C19 C20 C15 120.85(10) . . ?
C12 C21 C22 81.60(8) . . ?
C14 C22 C23 100.92(9) . . ?
C14 C22 C21 100.78(9) . . ?
C23 C22 C21 86.78(8) . . ?
C14 C22 C12 78.11(7) . . ?
C23 C22 C12 50.19(6) . . ?
C21 C22 C12 49.02(6) . . ?
C22 C23 C12 80.76(8) . . ?
C29 C24 C25 120.83(10) . . ?
C29 C24 S1 118.70(8) . . ?
C25 C24 S1 120.26(8) . . ?
C26 C25 C24 119.05(10) . . ?
C25 C26 C27 121.03(10) . . ?
C28 C27 C26 118.82(10) . . ?
C28 C27 C31 119.65(11) . . ?
C26 C27 C31 121.53(11) . . ?
C29 C28 C27 121.02(10) . . ?
C28 C29 C24 119.23(10) . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.057



