# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cd15228
_audit_block_doi                 10.5517/cc1k54wr
_database_code_depnum_ccdc_archive 'CCDC 1434924'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O S'
_chemical_formula_weight         372.47

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                   7.7469(8)
_cell_length_b                   17.4348(19)
_cell_length_c                   14.3624(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.609(2)
_cell_angle_gamma                90
_cell_volume                     1937.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2482
_cell_measurement_theta_min      4.673
_cell_measurement_theta_max      45.904

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_T_max  0.7457
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11485
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.838
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3825
_reflns_number_gt                2862
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0670P)²+0.3680P] 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         3825
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.41902(8) 0.25175(3) 0.12170(5) 0.0595(2) Uani 1 1 d . . . . .
N1 N 0.1784(2) 0.21008(9) 0.24421(12) 0.0438(4) Uani 1 1 d . . . . .
N2 N 1.0669(3) -0.18888(13) 0.0492(2) 0.0841(7) Uani 1 1 d . . . . .
O1 O 0.3276(2) -0.01110(9) 0.21150(13) 0.0681(5) Uani 1 1 d . . . . .
C1 C 0.3223(3) 0.18841(11) 0.19746(14) 0.0433(5) Uani 1 1 d . . . . .
C2 C 0.4029(2) 0.11822(11) 0.19768(14) 0.0409(5) Uani 1 1 d . . . . .
C3 C 0.5419(2) 0.11561(12) 0.13430(14) 0.0444(5) Uani 1 1 d . . . . .
C4 C 0.5658(3) 0.18387(14) 0.09196(16) 0.0555(6) Uani 1 1 d . . . . .
H4 H 0.6531 0.1929 0.0509 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3487(3) 0.05009(11) 0.25109(16) 0.0455(5) Uani 1 1 d . . . . .
C6 C 0.3272(3) 0.05687(13) 0.35288(16) 0.0526(6) Uani 1 1 d . . . . .
C7 C 0.2485(4) -0.00307(17) 0.3983(2) 0.0848(9) Uani 1 1 d . . . . .
H7 H 0.2072 -0.0455 0.3650 0.102 Uiso 1 1 calc R U . . .
C8 C 0.2323(6) 0.0012(3) 0.4939(3) 0.1207(15) Uani 1 1 d . . . . .
H8 H 0.1827 -0.0393 0.5253 0.145 Uiso 1 1 calc R U . . .
C9 C 0.2890(7) 0.0646(3) 0.5419(2) 0.1292(17) Uani 1 1 d . . . . .
H9 H 0.2747 0.0675 0.6057 0.155 Uiso 1 1 calc R U . . .
C10 C 0.3655(5) 0.1234(2) 0.4983(2) 0.1001(11) Uani 1 1 d . . . . .
H10 H 0.4043 0.1661 0.5320 0.120 Uiso 1 1 calc R U . . .
C11 C 0.3856(4) 0.11956(15) 0.40337(16) 0.0646(7) Uani 1 1 d . . . . .
H11 H 0.4391 0.1597 0.3733 0.078 Uiso 1 1 calc R U . . .
C12 C 0.6555(2) 0.04908(12) 0.11920(15) 0.0427(5) Uani 1 1 d . . . . .
C13 C 0.6937(3) 0.02910(13) 0.02845(15) 0.0478(5) Uani 1 1 d . . . . .
H13 H 0.6468 0.0574 -0.0215 0.057 Uiso 1 1 calc R U . . .
C14 C 0.8001(3) -0.03214(13) 0.01212(16) 0.0508(6) Uani 1 1 d . . . . .
H14 H 0.8236 -0.0453 -0.0488 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8722(3) -0.07401(12) 0.08529(17) 0.0498(5) Uani 1 1 d . . . . .
C16 C 0.8376(3) -0.05414(13) 0.17650(17) 0.0520(6) Uani 1 1 d . . . . .
H16 H 0.8874 -0.0817 0.2263 0.062 Uiso 1 1 calc R U . . .
C17 C 0.7289(3) 0.00667(12) 0.19248(15) 0.0491(5) Uani 1 1 d . . . . .
H17 H 0.7046 0.0194 0.2534 0.059 Uiso 1 1 calc R U . . .
C18 C 0.9813(3) -0.13832(14) 0.06670(19) 0.0609(6) Uani 1 1 d . . . . .
C19 C 0.0234(3) 0.16271(13) 0.23287(18) 0.0587(6) Uani 1 1 d . . . . .
H19A H 0.0558 0.1090 0.2303 0.070 Uiso 1 1 calc R U . . .
H19B H -0.0388 0.1757 0.1749 0.070 Uiso 1 1 calc R U . . .
C20 C -0.0913(3) 0.17561(15) 0.3133(2) 0.0734(8) Uani 1 1 d . . . . .
H20A H -0.0317 0.1591 0.3706 0.088 Uiso 1 1 calc R U . . .
H20B H -0.1954 0.1450 0.3043 0.088 Uiso 1 1 calc R U . . .
C21 C -0.1398(3) 0.25909(15) 0.3213(2) 0.0781(8) Uani 1 1 d . . . . .
H21A H -0.2050 0.2668 0.3766 0.094 Uiso 1 1 calc R U . . .
H21B H -0.2121 0.2742 0.2675 0.094 Uiso 1 1 calc R U . . .
C22 C 0.0214(3) 0.30784(14) 0.3271(2) 0.0673(7) Uani 1 1 d . . . . .
H22A H -0.0112 0.3616 0.3258 0.081 Uiso 1 1 calc R U . . .
H22B H 0.0841 0.2980 0.3859 0.081 Uiso 1 1 calc R U . . .
C23 C 0.1375(3) 0.29170(12) 0.24819(18) 0.0579(6) Uani 1 1 d . . . . .
H23A H 0.0806 0.3075 0.1898 0.070 Uiso 1 1 calc R U . . .
H23B H 0.2434 0.3210 0.2570 0.070 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 C4 1.709(2) . ?
S1 C1 1.743(2) . ?
N1 C1 1.380(3) . ?
N1 C23 1.459(3) . ?
N1 C19 1.461(3) . ?
N2 C18 1.138(3) . ?
O1 C5 1.216(2) . ?
C1 C2 1.374(3) . ?
C2 C3 1.442(3) . ?
C2 C5 1.485(3) . ?
C3 C4 1.353(3) . ?
C3 C12 1.478(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.484(3) . ?
C6 C11 1.377(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.386(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.366(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.351(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.387(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(3) . ?
C15 C18 1.437(3) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C20 1.506(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.509(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.510(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.506(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
C4 S1 C1 91.56(10) . . ?
C1 N1 C23 117.89(17) . . ?
C1 N1 C19 117.99(17) . . ?
C23 N1 C19 112.12(17) . . ?
C2 C1 N1 128.30(18) . . ?
C2 C1 S1 110.96(15) . . ?
N1 C1 S1 120.65(15) . . ?
C1 C2 C3 112.27(18) . . ?
C1 C2 C5 125.07(17) . . ?
C3 C2 C5 122.53(17) . . ?
C4 C3 C2 112.16(19) . . ?
C4 C3 C12 122.01(18) . . ?
C2 C3 C12 125.74(18) . . ?
C3 C4 S1 112.99(16) . . ?
C3 C4 H4 123.5 . . ?
S1 C4 H4 123.5 . . ?
O1 C5 C6 120.8(2) . . ?
O1 C5 C2 119.7(2) . . ?
C6 C5 C2 119.50(18) . . ?
C11 C6 C7 119.4(2) . . ?
C11 C6 C5 122.2(2) . . ?
C7 C6 C5 118.3(2) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C6 C11 C10 120.6(3) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C17 C12 C13 118.62(19) . . ?
C17 C12 C3 122.24(19) . . ?
C13 C12 C3 119.12(19) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 C18 119.6(2) . . ?
C16 C15 C18 120.6(2) . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
N2 C18 C15 178.0(3) . . ?
N1 C19 C20 109.94(19) . . ?
N1 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
N1 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 C21 111.1(2) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 C22 109.8(2) . . ?
C20 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
C20 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C23 C22 C21 112.0(2) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
N1 C23 C22 110.50(19) . . ?
N1 C23 H23A 109.6 . . ?
C22 C23 H23A 109.6 . . ?
N1 C23 H23B 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?

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
C23 N1 C1 C2 167.8(2) . . . . ?
C19 N1 C1 C2 -52.4(3) . . . . ?
C23 N1 C1 S1 -15.9(3) . . . . ?
C19 N1 C1 S1 123.92(19) . . . . ?
C4 S1 C1 C2 -0.26(17) . . . . ?
C4 S1 C1 N1 -177.15(18) . . . . ?
N1 C1 C2 C3 175.4(2) . . . . ?
S1 C1 C2 C3 -1.2(2) . . . . ?
N1 C1 C2 C5 -0.6(3) . . . . ?
S1 C1 C2 C5 -177.14(17) . . . . ?
C1 C2 C3 C4 2.5(3) . . . . ?
C5 C2 C3 C4 178.6(2) . . . . ?
C1 C2 C3 C12 179.04(19) . . . . ?
C5 C2 C3 C12 -4.9(3) . . . . ?
C2 C3 C4 S1 -2.8(2) . . . . ?
C12 C3 C4 S1 -179.39(16) . . . . ?
C1 S1 C4 C3 1.77(19) . . . . ?
C1 C2 C5 O1 128.7(2) . . . . ?
C3 C2 C5 O1 -46.9(3) . . . . ?
C1 C2 C5 C6 -53.6(3) . . . . ?
C3 C2 C5 C6 130.9(2) . . . . ?
O1 C5 C6 C11 165.5(2) . . . . ?
C2 C5 C6 C11 -12.3(3) . . . . ?
O1 C5 C6 C7 -13.2(3) . . . . ?
C2 C5 C6 C7 169.1(2) . . . . ?
C11 C6 C7 C8 -0.7(4) . . . . ?
C5 C6 C7 C8 177.9(3) . . . . ?
C6 C7 C8 C9 1.8(6) . . . . ?
C7 C8 C9 C10 -1.7(7) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C7 C6 C11 C10 -0.4(4) . . . . ?
C5 C6 C11 C10 -179.1(3) . . . . ?
C9 C10 C11 C6 0.6(5) . . . . ?
C4 C3 C12 C17 130.7(2) . . . . ?
C2 C3 C12 C17 -45.5(3) . . . . ?
C4 C3 C12 C13 -47.8(3) . . . . ?
C2 C3 C12 C13 136.0(2) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
C3 C12 C13 C14 179.45(18) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C13 C14 C15 C18 179.25(19) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C18 C15 C16 C17 -178.37(19) . . . . ?
C15 C16 C17 C12 -0.9(3) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C3 C12 C17 C16 -178.52(19) . . . . ?
C1 N1 C19 C20 158.4(2) . . . . ?
C23 N1 C19 C20 -59.6(3) . . . . ?
N1 C19 C20 C21 57.5(3) . . . . ?
C19 C20 C21 C22 -54.4(3) . . . . ?
C20 C21 C22 C23 53.1(3) . . . . ?
C1 N1 C23 C22 -159.9(2) . . . . ?
C19 N1 C23 C22 58.1(3) . . . . ?
C21 C22 C23 N1 -54.8(3) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4



