# 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_Y
_database_code_depnum_ccdc_archive 'CCDC 2216999'
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O4 S2'
_chemical_formula_weight         390.46

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                   13.181(2)
_cell_length_b                   8.8095(17)
_cell_length_c                   16.111(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.852(7)
_cell_angle_gamma                90
_cell_volume                     1799.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9088
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.50

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.323
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.947
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60544
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.628
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4144
_reflns_number_gt                3789
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0999P)²+3.6261P] 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         4144
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   0.657
_refine_ls_restrained_S_all      0.657
_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
C1 C 1.10019(19) 0.6961(3) 0.56618(15) 0.0521(6) Uani 1 1 d . . . . .
H1A H 1.0727 0.7439 0.6090 0.078 Uiso 1 1 calc R U . . .
H1B H 1.1711 0.7301 0.5726 0.078 Uiso 1 1 calc R U . . .
H1C H 1.0998 0.5880 0.5734 0.078 Uiso 1 1 calc R U . . .
C2 C 1.03211(9) 0.73771(16) 0.47687(6) 0.0349(4) Uani 1 1 d G . . . .
C3 C 0.94412(9) 0.82976(16) 0.46791(6) 0.0375(4) Uani 1 1 d G . . . .
H3 H 0.9274 0.8668 0.5166 0.045 Uiso 1 1 calc R U . . .
C4 C 0.88106(8) 0.86644(14) 0.38616(7) 0.0321(4) Uani 1 1 d G . . . .
H4 H 0.8222 0.9280 0.3802 0.039 Uiso 1 1 calc R U . . .
C5 C 0.90600(8) 0.81108(14) 0.31336(5) 0.0241(3) Uani 1 1 d G . . . .
C6 C 0.99399(9) 0.71903(15) 0.32231(6) 0.0339(4) Uani 1 1 d G . . . .
H6 H 1.0107 0.6820 0.2736 0.041 Uiso 1 1 calc R U . . .
C7 C 1.05704(8) 0.68234(15) 0.40407(8) 0.0407(5) Uani 1 1 d G . . . .
H7 H 1.1159 0.6208 0.4101 0.049 Uiso 1 1 calc R U . . .
C8 C 0.70107(12) 0.76748(19) 0.20114(11) 0.0247(3) Uani 1 1 d . . . . .
H8A H 0.6827 0.7780 0.2552 0.030 Uiso 1 1 calc R U . . .
H8B H 0.6473 0.8190 0.1569 0.030 Uiso 1 1 calc R U . . .
C9 C 0.70047(13) 0.60023(19) 0.17844(11) 0.0250(3) Uani 1 1 d . . . . .
H9 H 0.7325 0.5900 0.1305 0.030 Uiso 1 1 calc R U . . .
C10 C 0.75598(14) 0.4883(2) 0.24888(13) 0.0336(4) Uani 1 1 d . . . . .
H10A H 0.8311 0.4843 0.2545 0.040 Uiso 1 1 calc R U . . .
H10B H 0.7450 0.5154 0.3042 0.040 Uiso 1 1 calc R U . . .
C11 C 0.70276(14) 0.3375(2) 0.21616(13) 0.0351(4) Uani 1 1 d . . . . .
H11A H 0.7365 0.2883 0.1768 0.042 Uiso 1 1 calc R U . . .
H11B H 0.7034 0.2691 0.2635 0.042 Uiso 1 1 calc R U . . .
C12 C 0.59034(13) 0.53486(18) 0.14930(10) 0.0231(3) Uani 1 1 d . . . . .
C13 C 0.41665(8) 0.34150(9) 0.08341(7) 0.0239(3) Uani 1 1 d G . . . .
C14 C 0.33798(7) 0.24252(12) 0.03972(7) 0.0294(4) Uani 1 1 d G . . . .
H14 H 0.2737 0.2805 0.0069 0.035 Uiso 1 1 calc R U . . .
C15 C 0.35542(8) 0.08677(11) 0.04505(8) 0.0363(4) Uani 1 1 d G . . . .
H15 H 0.3028 0.0206 0.0158 0.044 Uiso 1 1 calc R U . . .
C16 C 0.45153(10) 0.02999(9) 0.09408(9) 0.0406(5) Uani 1 1 d G . . . .
H16 H 0.4632 -0.0742 0.0976 0.049 Uiso 1 1 calc R U . . .
C17 C 0.53019(8) 0.12897(12) 0.13778(8) 0.0356(4) Uani 1 1 d G . . . .
H17 H 0.5945 0.0910 0.1706 0.043 Uiso 1 1 calc R U . . .
C18 C 0.51275(7) 0.28472(11) 0.13244(7) 0.0254(3) Uani 1 1 d G . . . .
N1 N 0.50952(11) 0.61294(17) 0.10574(10) 0.0271(3) Uani 1 1 d . . . . .
N2 N 0.59429(11) 0.38642(16) 0.17124(9) 0.0249(3) Uani 1 1 d . . . . .
O1 O 0.80378(11) 1.01943(15) 0.21014(9) 0.0341(3) Uani 1 1 d . . . . .
O2 O 0.86976(10) 0.79635(16) 0.14594(8) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.34758(11) 0.56824(17) 0.15377(9) 0.0376(3) Uani 1 1 d . . . . .
O4 O 0.33395(11) 0.58587(16) -0.00027(9) 0.0368(3) Uani 1 1 d . . . . .
S1 S 0.82476(3) 0.85834(5) 0.21103(3) 0.02375(12) Uani 1 1 d . . . . .
S2 S 0.39352(3) 0.53677(5) 0.08423(3) 0.02390(12) Uani 1 1 d . . . . .


_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
C1 C2 1.518(2) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 S1 1.7530 . ?
C6 C7 1.3900 . ?
C8 C9 1.518(2) . ?
C8 S1 1.7839(16) . ?
C9 C12 1.512(2) . ?
C9 C10 1.530(2) . ?
C10 C11 1.528(3) . ?
C11 N2 1.479(2) . ?
C12 N1 1.301(2) . ?
C12 N2 1.352(2) . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C13 S2 1.7477 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 N2 1.4076(16) . ?
N1 S2 1.6182(15) . ?
O1 S1 1.4452(14) . ?
O2 S1 1.4454(13) . ?
O3 S2 1.4385(14) . ?
O4 S2 1.4398(14) . ?

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
C3 C2 C7 120.0 . . ?
C3 C2 C1 119.98(13) . . ?
C7 C2 C1 120.01(13) . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 S1 120.94(6) . . ?
C4 C5 S1 119.05(6) . . ?
C5 C6 C7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C9 C8 S1 113.68(12) . . ?
C12 C9 C8 112.70(14) . . ?
C12 C9 C10 102.06(13) . . ?
C8 C9 C10 118.48(15) . . ?
C11 C10 C9 102.89(14) . . ?
N2 C11 C10 101.93(14) . . ?
N1 C12 N2 128.31(15) . . ?
N1 C12 C9 122.78(15) . . ?
N2 C12 C9 108.78(14) . . ?
C14 C13 C18 120.0 . . ?
C14 C13 S2 120.91(6) . . ?
C18 C13 S2 118.93(6) . . ?
C13 C14 C15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C18 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 N2 120.50(9) . . ?
C13 C18 N2 119.34(9) . . ?
C12 N1 S2 118.88(12) . . ?
C12 N2 C18 121.96(13) . . ?
C12 N2 C11 111.88(14) . . ?
C18 N2 C11 123.40(13) . . ?
O1 S1 O2 118.62(9) . . ?
O1 S1 C5 107.98(7) . . ?
O2 S1 C5 109.04(7) . . ?
O1 S1 C8 105.78(8) . . ?
O2 S1 C8 108.17(8) . . ?
C5 S1 C8 106.62(7) . . ?
O3 S2 O4 116.21(9) . . ?
O3 S2 N1 109.11(8) . . ?
O4 S2 N1 108.50(8) . . ?
O3 S2 C13 107.88(8) . . ?
O4 S2 C13 109.86(7) . . ?
N1 S2 C13 104.67(7) . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.055

