# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_mo_hr011020_0ma_c-dc_sq_sq
_database_code_depnum_ccdc_archive 'CCDC 2116847'
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2021-10-24 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         'C52.16 H41 N2 O1.66 S2'
_chemical_formula_sum            'C52.16 H41 N2 O1.66 S2'
_chemical_formula_weight         786.52

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   22.5989(8)
_cell_length_b                   20.6160(7)
_cell_length_c                   9.7234(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4530.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.07

_exptl_crystal_description       block
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_F_000             1653
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1388 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.8554.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Photon II '
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53312
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         27.132
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5132
_reflns_number_gt                4400
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0911P)²+4.7466P] 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         5132
_refine_ls_number_parameters     284
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.1983
_refine_ls_wR_factor_gt          0.1920
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.119
_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
S1 S 0.64100(3) 0.66673(3) 0.53785(6) 0.03920(19) Uani 1 1 d . . . . .
O1 O 0.5407(8) 0.750000 0.9360(11) 0.313(8) Uani 1 2 d S T P . .
O2 O 0.5088(5) 0.6589(5) 1.6988(10) 0.100(4) Uani 0.331(8) 1 d . . P . .
N1 N 0.60671(9) 0.55421(12) 0.7239(2) 0.0481(5) Uani 1 1 d . . . . .
H1 H 0.605443 0.596805 0.718630 0.058 Uiso 1 1 calc R U . . .
C1 C 0.66205(10) 0.71541(12) 0.3999(2) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.67753(12) 0.67706(12) 0.2875(3) 0.0425(6) Uani 1 1 d . . . . .
H2 H 0.690780 0.694569 0.202571 0.051 Uiso 1 1 calc R U . . .
C3 C 0.67191(12) 0.61170(13) 0.3107(3) 0.0445(6) Uani 1 1 d . . . . .
H3 H 0.680536 0.580032 0.242648 0.053 Uiso 1 1 calc R U . . .
C4 C 0.65233(11) 0.59548(13) 0.4435(3) 0.0409(5) Uani 1 1 d . . . . .
C5 C 0.64390(11) 0.53108(13) 0.4904(3) 0.0439(6) Uani 1 1 d . . . . .
C6 C 0.65534(12) 0.47848(12) 0.3875(3) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.71281(13) 0.45630(14) 0.3623(3) 0.0541(7) Uani 1 1 d . . . . .
C8 C 0.72210(14) 0.41132(15) 0.2583(4) 0.0591(8) Uani 1 1 d . . . . .
H8 H 0.761193 0.396383 0.241257 0.071 Uiso 1 1 calc R U . . .
C9 C 0.67572(14) 0.38727(13) 0.1776(3) 0.0528(7) Uani 1 1 d . . . . .
C10 C 0.61902(13) 0.40809(14) 0.2093(3) 0.0517(6) Uani 1 1 d . . . . .
H10 H 0.586599 0.390823 0.159014 0.062 Uiso 1 1 calc R U . . .
C11 C 0.60797(12) 0.45339(13) 0.3120(3) 0.0477(6) Uani 1 1 d . . . . .
C12 C 0.54518(12) 0.47404(17) 0.3436(3) 0.0570(7) Uani 1 1 d . . . . .
H12A H 0.519490 0.462919 0.265891 0.085 Uiso 1 1 calc R U . . .
H12B H 0.544050 0.521004 0.358968 0.085 Uiso 1 1 calc R U . . .
H12C H 0.531322 0.451574 0.426370 0.085 Uiso 1 1 calc R U . . .
C13 C 0.76443(15) 0.4805(2) 0.4468(4) 0.0783(11) Uani 1 1 d . . . . .
H13A H 0.798161 0.451100 0.434983 0.117 Uiso 1 1 calc R U . . .
H13B H 0.753140 0.481825 0.544049 0.117 Uiso 1 1 calc R U . . .
H13C H 0.775462 0.524089 0.416116 0.117 Uiso 1 1 calc R U . . .
C14 C 0.68752(17) 0.34062(15) 0.0626(4) 0.0668(9) Uani 1 1 d . . . . .
H14A H 0.650890 0.317735 0.038968 0.100 Uiso 1 1 calc R U . . .
H14B H 0.717536 0.309147 0.091543 0.100 Uiso 1 1 calc R U . . .
H14C H 0.701843 0.364472 -0.017995 0.100 Uiso 1 1 calc R U . . .
C15 C 0.62471(12) 0.51262(14) 0.6214(3) 0.0474(6) Uani 1 1 d . . . . .
C16 C 0.62081(15) 0.44730(15) 0.6716(3) 0.0592(8) Uani 1 1 d . . . . .
H16 H 0.630571 0.408919 0.622572 0.071 Uiso 1 1 calc R U . . .
C17 C 0.60050(15) 0.45092(17) 0.8027(4) 0.0656(9) Uani 1 1 d . . . . .
H17 H 0.593639 0.415334 0.862683 0.079 Uiso 1 1 calc R U . . .
C18 C 0.59127(13) 0.51779(15) 0.8344(3) 0.0549(7) Uani 1 1 d . . . . .
C19 C 0.56815(14) 0.54342(18) 0.9581(3) 0.0634(9) Uani 1 1 d . . . . .
H19 H 0.559973 0.513621 1.030153 0.076 Uiso 1 1 calc R U . . .
C20 C 0.55658(13) 0.60740(18) 0.9828(3) 0.0619(8) Uani 1 1 d . . . . .
H20 H 0.563067 0.637897 0.911104 0.074 Uiso 1 1 calc R U . . .
C21 C 0.53547(15) 0.6299(2) 1.1101(4) 0.0702(10) Uani 1 1 d . . . . .
H21 H 0.527805 0.597898 1.178145 0.084 Uiso 1 1 calc R U . . .
C22 C 0.52484(14) 0.69250(19) 1.1461(3) 0.0628(8) Uani 1 1 d . . . . .
C23 C 0.5333(2) 0.750000 1.0635(5) 0.0671(13) Uani 1 2 d S T P . .
C24 C 0.50751(13) 0.7154(2) 1.2836(3) 0.0727(11) Uani 1 1 d . . . . .
C25 C 0.49465(17) 0.6811(3) 1.4025(4) 0.0954(15) Uani 1 1 d . U . . .
H25 H 0.494275 0.635040 1.402838 0.114 Uiso 1 1 calc R U . . .
C26 C 0.48213(17) 0.7167(3) 1.5230(4) 0.1030(16) Uani 1 1 d . U . . .
C27 C 0.4836(5) 0.7053(5) 1.6621(10) 0.068(3) Uani 0.331(8) 1 d . . P . .
C28 C 0.4610(10) 0.750000 1.7562(14) 0.169(9) Uani 0.5 2 d S T P . .
H28A H 0.480740 0.749999 1.847086 0.203 Uiso 0.5 2 calc R U P . .
H28B H 0.417328 0.750000 1.764897 0.203 Uiso 0.5 2 calc R U P . .


_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 C1 1.742(2) . ?
S1 C4 1.750(3) . ?
O1 C23 1.251(10) . ?
O2 C27 1.170(13) . ?
N1 C18 1.357(3) . ?
N1 C15 1.376(4) . ?
C1 C2 1.393(3) . ?
C1 C1 1.426(5) 7_575 ?
C2 C3 1.372(4) . ?
C3 C4 1.405(3) . ?
C4 C5 1.417(4) . ?
C5 C15 1.399(4) . ?
C5 C6 1.498(4) . ?
C6 C11 1.397(4) . ?
C6 C7 1.399(4) . ?
C7 C8 1.388(4) . ?
C7 C13 1.511(5) . ?
C8 C9 1.400(5) . ?
C9 C10 1.386(4) . ?
C9 C14 1.499(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.513(4) . ?
C15 C16 1.435(4) . ?
C16 C17 1.357(5) . ?
C17 C18 1.428(5) . ?
C18 C19 1.414(5) . ?
C19 C20 1.366(5) . ?
C20 C21 1.405(5) . ?
C21 C22 1.359(5) . ?
C22 C23 1.444(4) . ?
C22 C24 1.471(4) . ?
C24 C25 1.386(5) . ?
C24 C24 1.426(9) 7_575 ?
C25 C26 1.411(6) . ?
C26 C26 1.372(11) 7_575 ?
C26 C27 1.373(10) . ?
C27 C28 1.395(14) . ?
C27 C27 1.84(2) 7_575 ?

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 S1 C4 92.30(12) . . ?
C18 N1 C15 107.7(2) . . ?
C2 C1 C1 124.58(14) . 7_575 ?
C2 C1 S1 110.21(18) . . ?
C1 C1 S1 125.19(8) 7_575 . ?
C3 C2 C1 113.9(2) . . ?
C2 C3 C4 114.4(2) . . ?
C3 C4 C5 124.1(2) . . ?
C3 C4 S1 109.14(19) . . ?
C5 C4 S1 126.8(2) . . ?
C15 C5 C4 126.1(3) . . ?
C15 C5 C6 117.7(2) . . ?
C4 C5 C6 116.1(2) . . ?
C11 C6 C7 119.9(3) . . ?
C11 C6 C5 119.1(2) . . ?
C7 C6 C5 120.9(3) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 C13 120.0(3) . . ?
C6 C7 C13 120.9(3) . . ?
C7 C8 C9 122.1(3) . . ?
C10 C9 C8 117.3(3) . . ?
C10 C9 C14 121.9(3) . . ?
C8 C9 C14 120.8(3) . . ?
C9 C10 C11 122.3(3) . . ?
C10 C11 C6 119.2(3) . . ?
C10 C11 C12 120.2(3) . . ?
C6 C11 C12 120.5(3) . . ?
N1 C15 C5 125.6(2) . . ?
N1 C15 C16 108.7(2) . . ?
C5 C15 C16 125.8(3) . . ?
C17 C16 C15 106.8(3) . . ?
C16 C17 C18 107.8(3) . . ?
N1 C18 C19 124.2(3) . . ?
N1 C18 C17 109.0(3) . . ?
C19 C18 C17 126.8(3) . . ?
C20 C19 C18 125.5(3) . . ?
C19 C20 C21 122.6(3) . . ?
C22 C21 C20 126.9(3) . . ?
C21 C22 C23 127.8(3) . . ?
C21 C22 C24 125.9(3) . . ?
C23 C22 C24 106.1(3) . . ?
O1 C23 C22 124.6(2) . 7_575 ?
O1 C23 C22 124.6(2) . . ?
C22 C23 C22 110.3(4) 7_575 . ?
C25 C24 C24 120.7(3) . 7_575 ?
C25 C24 C22 130.5(4) . . ?
C24 C24 C22 108.7(2) 7_575 . ?
C24 C25 C26 118.0(5) . . ?
C26 C26 C27 99.9(5) 7_575 . ?
C26 C26 C25 121.3(3) 7_575 . ?
C27 C26 C25 136.4(6) . . ?
O2 C27 C26 116.9(10) . . ?
O2 C27 C28 121.2(11) . . ?
C26 C27 C28 121.6(9) . . ?
O2 C27 C27 144.9(9) . 7_575 ?
C26 C27 C27 80.1(5) . 7_575 ?
C28 C27 C27 48.7(6) . 7_575 ?
C27 C28 C27 82.6(11) . 7_575 ?

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
C4 S1 C1 C2 -0.6(2) . . . . ?
C4 S1 C1 C1 177.86(10) . . . 7_575 ?
C1 C1 C2 C3 -177.61(17) 7_575 . . . ?
S1 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 -179.4(3) . . . . ?
C2 C3 C4 S1 0.2(3) . . . . ?
C1 S1 C4 C3 0.2(2) . . . . ?
C1 S1 C4 C5 179.9(2) . . . . ?
C3 C4 C5 C15 179.8(3) . . . . ?
S1 C4 C5 C15 0.2(4) . . . . ?
C3 C4 C5 C6 -1.9(4) . . . . ?
S1 C4 C5 C6 178.51(19) . . . . ?
C15 C5 C6 C11 83.6(3) . . . . ?
C4 C5 C6 C11 -94.9(3) . . . . ?
C15 C5 C6 C7 -99.1(3) . . . . ?
C4 C5 C6 C7 82.4(3) . . . . ?
C11 C6 C7 C8 2.5(4) . . . . ?
C5 C6 C7 C8 -174.8(3) . . . . ?
C11 C6 C7 C13 -177.2(3) . . . . ?
C5 C6 C7 C13 5.5(4) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C13 C7 C8 C9 179.7(3) . . . . ?
C7 C8 C9 C10 -2.7(5) . . . . ?
C7 C8 C9 C14 177.7(3) . . . . ?
C8 C9 C10 C11 3.1(4) . . . . ?
C14 C9 C10 C11 -177.3(3) . . . . ?
C9 C10 C11 C6 -0.7(4) . . . . ?
C9 C10 C11 C12 -179.4(3) . . . . ?
C7 C6 C11 C10 -2.2(4) . . . . ?
C5 C6 C11 C10 175.2(2) . . . . ?
C7 C6 C11 C12 176.5(3) . . . . ?
C5 C6 C11 C12 -6.2(4) . . . . ?
C18 N1 C15 C5 179.7(3) . . . . ?
C18 N1 C15 C16 -0.7(3) . . . . ?
C4 C5 C15 N1 5.0(5) . . . . ?
C6 C5 C15 N1 -173.4(2) . . . . ?
C4 C5 C15 C16 -174.7(3) . . . . ?
C6 C5 C15 C16 7.0(4) . . . . ?
N1 C15 C16 C17 0.1(4) . . . . ?
C5 C15 C16 C17 179.8(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C15 N1 C18 C19 -177.3(3) . . . . ?
C15 N1 C18 C17 0.9(3) . . . . ?
C16 C17 C18 N1 -0.8(4) . . . . ?
C16 C17 C18 C19 177.3(3) . . . . ?
N1 C18 C19 C20 1.9(5) . . . . ?
C17 C18 C19 C20 -176.0(3) . . . . ?
C18 C19 C20 C21 -177.8(3) . . . . ?
C19 C20 C21 C22 177.3(3) . . . . ?
C20 C21 C22 C23 -0.7(6) . . . . ?
C20 C21 C22 C24 -174.5(3) . . . . ?
C21 C22 C23 O1 15.1(13) . . . . ?
C24 C22 C23 O1 -170.1(11) . . . . ?
C21 C22 C23 C22 -171.8(3) . . . 7_575 ?
C24 C22 C23 C22 2.9(5) . . . 7_575 ?
C21 C22 C24 C25 -4.4(6) . . . . ?
C23 C22 C24 C25 -179.3(4) . . . . ?
C21 C22 C24 C24 173.1(3) . . . 7_575 ?
C23 C22 C24 C24 -1.8(3) . . . 7_575 ?
C24 C24 C25 C26 -0.5(4) 7_575 . . . ?
C22 C24 C25 C26 176.7(3) . . . . ?
C24 C25 C26 C26 0.5(5) . . . 7_575 ?
C24 C25 C26 C27 -157.9(9) . . . . ?
C26 C26 C27 O2 -147.5(11) 7_575 . . . ?
C25 C26 C27 O2 13.9(18) . . . . ?
C26 C26 C27 C28 26.6(15) 7_575 . . . ?
C25 C26 C27 C28 -172.0(12) . . . . ?
C26 C26 C27 C27 -0.002(5) 7_575 . . 7_575 ?
C25 C26 C27 C27 161.4(9) . . . 7_575 ?
O2 C27 C28 C27 137.8(10) . . . 7_575 ?
C26 C27 C28 C27 -36.0(19) . . . 7_575 ?

_refine_diff_density_max         0.964
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.060



