# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_UJ
_database_code_depnum_ccdc_archive 'CCDC 1964540'
_audit_update_record             
;
2019-11-08 deposited with the CCDC.	2020-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 N O2 S'
_chemical_formula_weight         435.52

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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.7300(20)
_cell_length_b                   20.980(4)
_cell_length_c                   11.450(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.39(3)
_cell_angle_gamma                90
_cell_volume                     2264.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5170
_cell_measurement_theta_min      1.941
_cell_measurement_theta_max      27.45

_exptl_crystal_description       'Rod Shaped'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   0.6918
_shelx_estimated_absorpt_T_max   0.7456
_exptl_absorpt_correction_type   none
_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                   X-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37120
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.941
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5164
_reflns_number_gt                2650
_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, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1000P)²] 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         5164
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_restrained_S_all      0.861
_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 -0.00553(7) 0.11957(3) 0.10677(5) 0.0479(2) Uani 1 1 d . . . . .
N1 N 0.1055(2) 0.11584(9) 0.24190(17) 0.0415(5) Uani 1 1 d . . . . .
O1 O 0.0346(2) 0.07101(8) 0.03510(15) 0.0644(6) Uani 1 1 d . . . . .
C1 C -0.5590(4) 0.0528(2) 0.2221(4) 0.1278(16) Uani 1 1 d . . . . .
H1B H -0.584128 0.009640 0.197824 0.192 Uiso 1 1 calc R U . . .
H1C H -0.546756 0.056671 0.307566 0.192 Uiso 1 1 calc R U . . .
H1D H -0.633128 0.080962 0.181111 0.192 Uiso 1 1 calc R U . . .
O2 O -0.0057(2) 0.18484(8) 0.07207(14) 0.0592(5) Uani 1 1 d . . . . .
C2 C -0.4233(3) 0.06998(17) 0.1903(3) 0.0735(9) Uani 1 1 d . . . . .
C3 C -0.3529(4) 0.02549(15) 0.1367(3) 0.0777(9) Uani 1 1 d . . . . .
H3A H -0.391416 -0.015032 0.119712 0.093 Uiso 1 1 calc R U . . .
C4 C 0.5757(4) 0.13978(16) 0.7362(4) 0.0804(10) Uani 1 1 d . . . . .
H4A H 0.666685 0.128475 0.731828 0.096 Uiso 1 1 calc R U . . .
C5 C 0.5419(4) 0.13904(15) 0.8453(4) 0.0803(10) Uani 1 1 d . . . . .
H5A H 0.610850 0.127463 0.913948 0.096 Uiso 1 1 calc R U . . .
C6 C -0.1226(3) 0.22721(13) 0.6493(3) 0.0641(8) Uani 1 1 d . . . . .
H6A H -0.216906 0.239647 0.622097 0.077 Uiso 1 1 calc R U . . .
C7 C 0.1779(3) -0.02815(14) 0.4951(3) 0.0696(9) Uani 1 1 d . . . . .
H7A H 0.196296 -0.059037 0.555255 0.083 Uiso 1 1 calc R U . . .
C8 C -0.0657(4) 0.21714(14) 0.7702(3) 0.0709(9) Uani 1 1 d . . . . .
H8A H -0.122256 0.223014 0.823977 0.085 Uiso 1 1 calc R U . . .
C9 C 0.4764(3) 0.15708(13) 0.6327(3) 0.0646(8) Uani 1 1 d . . . . .
H9A H 0.499813 0.157748 0.558780 0.078 Uiso 1 1 calc R U . . .
C10 C -0.3626(3) 0.12983(15) 0.2154(3) 0.0684(9) Uani 1 1 d . . . . .
H10A H -0.408398 0.160240 0.251293 0.082 Uiso 1 1 calc R U . . .
C11 C 0.0734(4) 0.19853(13) 0.8135(2) 0.0610(8) Uani 1 1 d . . . . .
H11A H 0.110419 0.191164 0.895388 0.073 Uiso 1 1 calc R U . . .
C12 C -0.0399(3) 0.21888(12) 0.5677(2) 0.0546(7) Uani 1 1 d . . . . .
H12A H -0.078641 0.224780 0.485627 0.066 Uiso 1 1 calc R U . . .
C13 C -0.2272(3) 0.04005(13) 0.1082(3) 0.0592(7) Uani 1 1 d . . . . .
H13A H -0.181810 0.009813 0.071661 0.071 Uiso 1 1 calc R U . . .
C14 C 0.4081(4) 0.15507(13) 0.8556(3) 0.0675(9) Uani 1 1 d . . . . .
H14A H 0.385987 0.154265 0.930092 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1057(3) -0.00314(12) 0.2840(2) 0.0522(7) Uani 1 1 d . . . . .
H15A H 0.076252 -0.015807 0.203825 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3065(3) 0.17259(11) 0.7510(2) 0.0490(7) Uani 1 1 d . . . . .
C17 C 0.1314(3) -0.04678(13) 0.3760(3) 0.0630(8) Uani 1 1 d . . . . .
H17A H 0.117162 -0.089862 0.357936 0.076 Uiso 1 1 calc R U . . .
C18 C 0.1977(3) 0.03514(14) 0.5267(3) 0.0615(8) Uani 1 1 d . . . . .
H18A H 0.228737 0.047098 0.607131 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1576(3) 0.19095(11) 0.7321(2) 0.0471(6) Uani 1 1 d . . . . .
C20 C -0.2372(3) 0.14532(13) 0.1888(2) 0.0540(7) Uani 1 1 d . . . . .
H20A H -0.197862 0.185628 0.206782 0.065 Uiso 1 1 calc R U . . .
C21 C 0.1012(3) 0.20166(11) 0.6101(2) 0.0442(6) Uani 1 1 d . . . . .
C22 C -0.1693(3) 0.09999(12) 0.1344(2) 0.0449(6) Uani 1 1 d . . . . .
C23 C 0.3418(3) 0.17337(12) 0.6406(2) 0.0489(7) Uani 1 1 d . . . . .
C24 C 0.1254(2) 0.06059(12) 0.3154(2) 0.0420(6) Uani 1 1 d . . . . .
C25 C 0.1335(3) 0.16902(12) 0.3197(2) 0.0431(6) Uani 1 1 d . . . . .
H25A H 0.124430 0.211283 0.294389 0.052 Uiso 1 1 calc R U . . .
C26 C 0.1701(3) 0.08103(11) 0.4355(2) 0.0427(6) Uani 1 1 d . . . . .
C27 C 0.1748(3) 0.15030(11) 0.4345(2) 0.0418(6) Uani 1 1 d . . . . .
C28 C 0.2147(3) 0.19410(12) 0.5416(2) 0.0453(6) Uani 1 1 d . . . . .
H28A H 0.235100 0.236251 0.513059 0.054 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 O1 1.4222(17) . ?
S1 O2 1.4258(17) . ?
S1 N1 1.654(2) . ?
S1 C22 1.748(3) . ?
N1 C25 1.411(3) . ?
N1 C24 1.417(3) . ?
C1 C2 1.499(4) . ?
C2 C10 1.387(4) . ?
C2 C3 1.388(4) . ?
C3 C13 1.376(4) . ?
C4 C5 1.368(5) . ?
C4 C9 1.379(4) . ?
C5 C14 1.378(4) . ?
C6 C8 1.373(4) . ?
C6 C12 1.388(4) . ?
C7 C18 1.377(4) . ?
C7 C17 1.382(4) . ?
C8 C11 1.377(4) . ?
C9 C23 1.378(4) . ?
C10 C20 1.369(4) . ?
C11 C19 1.395(4) . ?
C12 C21 1.385(3) . ?
C13 C22 1.380(4) . ?
C14 C16 1.400(4) . ?
C15 C17 1.371(4) . ?
C15 C24 1.386(3) . ?
C16 C23 1.390(3) . ?
C16 C19 1.462(4) . ?
C18 C26 1.396(3) . ?
C19 C21 1.386(3) . ?
C20 C22 1.390(4) . ?
C21 C28 1.513(3) . ?
C23 C28 1.519(3) . ?
C24 C26 1.402(3) . ?
C25 C27 1.335(3) . ?
C26 C27 1.454(3) . ?
C27 C28 1.504(3) . ?

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
O1 S1 O2 120.57(11) . . ?
O1 S1 N1 107.26(11) . . ?
O2 S1 N1 105.14(10) . . ?
O1 S1 C22 109.21(12) . . ?
O2 S1 C22 109.77(11) . . ?
N1 S1 C22 103.44(11) . . ?
C25 N1 C24 107.19(19) . . ?
C25 N1 S1 122.11(16) . . ?
C24 N1 S1 123.73(16) . . ?
C10 C2 C3 118.0(3) . . ?
C10 C2 C1 121.5(3) . . ?
C3 C2 C1 120.5(3) . . ?
C13 C3 C2 121.4(3) . . ?
C5 C4 C9 120.8(3) . . ?
C4 C5 C14 121.5(3) . . ?
C8 C6 C12 120.2(3) . . ?
C18 C7 C17 121.4(3) . . ?
C6 C8 C11 121.4(3) . . ?
C23 C9 C4 118.9(3) . . ?
C20 C10 C2 121.7(3) . . ?
C8 C11 C19 118.7(3) . . ?
C21 C12 C6 119.1(3) . . ?
C3 C13 C22 119.4(3) . . ?
C5 C14 C16 118.2(3) . . ?
C17 C15 C24 117.3(3) . . ?
C23 C16 C14 119.9(3) . . ?
C23 C16 C19 108.8(2) . . ?
C14 C16 C19 131.3(3) . . ?
C15 C17 C7 121.5(3) . . ?
C7 C18 C26 118.7(3) . . ?
C21 C19 C11 120.3(3) . . ?
C21 C19 C16 108.8(2) . . ?
C11 C19 C16 131.0(2) . . ?
C10 C20 C22 119.1(3) . . ?
C12 C21 C19 120.3(2) . . ?
C12 C21 C28 129.3(2) . . ?
C19 C21 C28 110.4(2) . . ?
C13 C22 C20 120.4(3) . . ?
C13 C22 S1 121.1(2) . . ?
C20 C22 S1 118.4(2) . . ?
C9 C23 C16 120.7(3) . . ?
C9 C23 C28 129.2(2) . . ?
C16 C23 C28 110.0(2) . . ?
C15 C24 C26 122.6(2) . . ?
C15 C24 N1 130.2(2) . . ?
C26 C24 N1 107.2(2) . . ?
C27 C25 N1 110.6(2) . . ?
C18 C26 C24 118.5(2) . . ?
C18 C26 C27 133.9(2) . . ?
C24 C26 C27 107.5(2) . . ?
C25 C27 C26 107.4(2) . . ?
C25 C27 C28 125.2(2) . . ?
C26 C27 C28 127.4(2) . . ?
C27 C28 C21 114.4(2) . . ?
C27 C28 C23 115.5(2) . . ?
C21 C28 C23 101.92(19) . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.047

