# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_mo_d8v20849_0m
_database_code_depnum_ccdc_archive 'CCDC 2201657'
loop_
_audit_author_name
_audit_author_address
'Lu Cheng'
;ecnu
China
;
_audit_update_record             
;
2022-08-16 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H26 N2 O2 S2'
_chemical_formula_weight         582.71

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   16.5229(12)
_cell_length_b                   10.3183(8)
_cell_length_c                   19.3418(16)
_cell_angle_alpha                90
_cell_angle_beta                 114.004(2)
_cell_angle_gamma                90
_cell_volume                     3012.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      4.611
_cell_measurement_theta_max      54.941

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            21487
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2917
_reflns_number_gt                2657
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0479P)²+1.9655P] 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     SHELXL
_refine_ls_extinction_coef       0.0056(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.005

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 0.60058(2) 0.01319(4) 0.80700(2) 0.04392(17) Uani 1 1 d . . . . .
O1 O 0.40547(11) 0.07469(14) 0.53483(7) 0.0776(5) Uani 1 1 d . . . . .
N1 N 0.40079(9) 0.36016(15) 0.52647(7) 0.0534(4) Uani 1 1 d . . . . .
C1 C 0.42218(12) 0.48714(18) 0.54701(11) 0.0567(4) Uani 1 1 d . . . . .
C2 C 0.39590(16) 0.6020(2) 0.50406(14) 0.0806(7) Uani 1 1 d . . . . .
H2 H 0.3573 0.6005 0.4532 0.097 Uiso 1 1 calc R U . . .
C3 C 0.42990(19) 0.7160(2) 0.54079(18) 0.0908(8) Uani 1 1 d . . . . .
H3 H 0.4139 0.7931 0.5136 0.109 Uiso 1 1 calc R U . . .
C4 C 0.48717(17) 0.7215(2) 0.61668(17) 0.0818(7) Uani 1 1 d . . . . .
H4 H 0.5083 0.8013 0.6390 0.098 Uiso 1 1 calc R U . . .
C5 C 0.51283(14) 0.61167(17) 0.65879(13) 0.0668(5) Uani 1 1 d . . . . .
H5 H 0.5513 0.6156 0.7097 0.080 Uiso 1 1 calc R U . . .
C6 C 0.47997(12) 0.49152(16) 0.62385(10) 0.0516(4) Uani 1 1 d . . . . .
C7 C 0.49265(11) 0.36253(15) 0.64977(9) 0.0463(4) Uani 1 1 d . . . . .
H7 H 0.5274 0.3357 0.6989 0.056 Uiso 1 1 calc R U . . .
C8 C 0.44478(10) 0.28294(15) 0.58985(8) 0.0431(4) Uani 1 1 d . . . . .
C9 C 0.44191(10) 0.14244(16) 0.59056(8) 0.0452(4) Uani 1 1 d . . . . .
C10 C 0.48235(9) 0.07921(13) 0.66757(8) 0.0386(3) Uani 1 1 d . . . . .
C11 C 0.56831(9) 0.07460(13) 0.71403(8) 0.0382(3) Uani 1 1 d . . . . .
C12 C 0.64238(9) 0.11647(14) 0.69497(8) 0.0412(3) Uani 1 1 d . . . . .
C13 C 0.70428(11) 0.20681(17) 0.73926(10) 0.0542(4) Uani 1 1 d . . . . .
H13 H 0.6995 0.2418 0.7818 0.065 Uiso 1 1 calc R U . . .
C14 C 0.77261(13) 0.2446(2) 0.72028(12) 0.0690(5) Uani 1 1 d . . . . .
H14 H 0.8127 0.3071 0.7491 0.083 Uiso 1 1 calc R U . . .
C15 C 0.78187(13) 0.1905(2) 0.65894(12) 0.0734(6) Uani 1 1 d . . . . .
H15 H 0.8285 0.2156 0.6467 0.088 Uiso 1 1 calc R U . . .
C16 C 0.72238(13) 0.0996(2) 0.61582(11) 0.0672(5) Uani 1 1 d . . . . .
H16 H 0.7292 0.0625 0.5747 0.081 Uiso 1 1 calc R U . . .
C17 C 0.65206(11) 0.06247(18) 0.63301(9) 0.0525(4) Uani 1 1 d . . . . .
H17 H 0.6114 0.0015 0.6031 0.063 Uiso 1 1 calc R U . . .
C18 C 0.33752(14) 0.3185(3) 0.45179(10) 0.0797(6) Uani 1 1 d . . . . .
H18A H 0.3363 0.2255 0.4494 0.120 Uiso 1 1 calc R U . . .
H18B H 0.3551 0.3523 0.4137 0.120 Uiso 1 1 calc R U . . .
H18C H 0.2796 0.3503 0.4432 0.120 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 C10 1.7697(14) 2_656 ?
S1 C11 1.7718(14) . ?
O1 C9 1.2186(18) . ?
N1 C1 1.373(2) . ?
N1 C8 1.3932(19) . ?
N1 C18 1.461(2) . ?
C1 C6 1.403(3) . ?
C1 C2 1.411(3) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(2) . ?
C7 C8 1.377(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.451(2) . ?
C9 C10 1.510(2) . ?
C10 C11 1.337(2) . ?
C10 S1 1.7697(14) 2_656 ?
C11 C12 1.4791(19) . ?
C12 C17 1.389(2) . ?
C12 C13 1.391(2) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C10 S1 C11 101.37(6) 2_656 . ?
C1 N1 C8 108.09(13) . . ?
C1 N1 C18 124.27(16) . . ?
C8 N1 C18 127.51(17) . . ?
N1 C1 C6 108.75(14) . . ?
N1 C1 C2 130.55(19) . . ?
C6 C1 C2 120.7(2) . . ?
C3 C2 C1 116.9(2) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 122.9(2) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 106.58(15) . . ?
C1 C6 C5 119.95(16) . . ?
C7 C6 C5 133.47(18) . . ?
C8 C7 C6 108.23(14) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
C7 C8 N1 108.35(14) . . ?
C7 C8 C9 126.70(13) . . ?
N1 C8 C9 124.92(14) . . ?
O1 C9 C8 124.84(15) . . ?
O1 C9 C10 119.05(15) . . ?
C8 C9 C10 115.97(12) . . ?
C11 C10 C9 126.93(13) . . ?
C11 C10 S1 122.02(11) . 2_656 ?
C9 C10 S1 111.01(10) . 2_656 ?
C10 C11 C12 125.62(13) . . ?
C10 C11 S1 119.57(11) . . ?
C12 C11 S1 114.81(10) . . ?
C17 C12 C13 119.10(15) . . ?
C17 C12 C11 119.70(13) . . ?
C13 C12 C11 121.18(14) . . ?
C14 C13 C12 120.16(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.38(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.96(17) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.49(18) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 119.87(16) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C8 N1 C1 C6 -0.09(19) . . . . ?
C18 N1 C1 C6 175.96(16) . . . . ?
C8 N1 C1 C2 179.49(19) . . . . ?
C18 N1 C1 C2 -4.5(3) . . . . ?
N1 C1 C2 C3 -179.1(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
N1 C1 C6 C7 -0.4(2) . . . . ?
C2 C1 C6 C7 179.92(17) . . . . ?
N1 C1 C6 C5 179.25(16) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 179.78(19) . . . . ?
C1 C6 C7 C8 0.82(19) . . . . ?
C5 C6 C7 C8 -178.81(19) . . . . ?
C6 C7 C8 N1 -0.89(18) . . . . ?
C6 C7 C8 C9 177.23(15) . . . . ?
C1 N1 C8 C7 0.61(18) . . . . ?
C18 N1 C8 C7 -175.27(16) . . . . ?
C1 N1 C8 C9 -177.55(15) . . . . ?
C18 N1 C8 C9 6.6(3) . . . . ?
C7 C8 C9 O1 -172.74(17) . . . . ?
N1 C8 C9 O1 5.1(3) . . . . ?
C7 C8 C9 C10 11.6(2) . . . . ?
N1 C8 C9 C10 -170.63(13) . . . . ?
O1 C9 C10 C11 114.49(18) . . . . ?
C8 C9 C10 C11 -69.5(2) . . . . ?
O1 C9 C10 S1 -67.75(18) . . . 2_656 ?
C8 C9 C10 S1 108.21(13) . . . 2_656 ?
C9 C10 C11 C12 -8.3(2) . . . . ?
S1 C10 C11 C12 174.19(11) 2_656 . . . ?
C9 C10 C11 S1 172.10(11) . . . . ?
S1 C10 C11 S1 -5.42(17) 2_656 . . . ?
C10 S1 C11 C10 -39.82(11) 2_656 . . . ?
C10 S1 C11 C12 140.52(11) 2_656 . . . ?
C10 C11 C12 C17 -56.4(2) . . . . ?
S1 C11 C12 C17 123.20(14) . . . . ?
C10 C11 C12 C13 125.32(17) . . . . ?
S1 C11 C12 C13 -55.05(18) . . . . ?
C17 C12 C13 C14 1.9(3) . . . . ?
C11 C12 C13 C14 -179.83(17) . . . . ?
C12 C13 C14 C15 -2.1(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C12 -0.8(3) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C11 C12 C17 C16 -178.75(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18A O1 0.96 2.22 2.950(3) 132.2 .

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

