# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2341377'
loop_
_audit_author_name
_audit_author_address
'Min Liu'
;The Shanghai Jiao Tong Crystallographic Data Centre
China
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 N O S'
_chemical_formula_sum            'C19 H23 N O S'
_chemical_formula_weight         313.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.7083(3)
_cell_length_b                   17.0851(9)
_cell_length_c                   17.0851(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1666.26(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      68.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.721
_shelx_estimated_absorpt_T_min   0.703
_shelx_estimated_absorpt_T_max   0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24611
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.659
_diffrn_reflns_theta_max         68.286
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3036
_reflns_number_gt                2976
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.995

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0644P)²+0.4221P] 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_abs_structure_details 
;
 Flack x determined using 1200 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3036
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.46416(9) 0.62431(3) 0.54418(3) 0.01985(16) Uani 1 1 d . . . . .
O1 O 0.3079(3) 0.69449(9) 0.54290(10) 0.0276(4) Uani 1 1 d . . . . .
C1 C 0.7133(4) 0.26079(14) 0.38836(12) 0.0235(5) Uani 1 1 d . . . . .
C6 C 0.8947(6) 0.22145(16) 0.42512(18) 0.0416(7) Uani 1 1 d . . . . .
H6 H 1.014076 0.250880 0.450314 0.050 Uiso 1 1 calc R U . . .
C7 C 0.6936(4) 0.34812(13) 0.39027(13) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.8649(4) 0.39467(14) 0.42508(15) 0.0264(5) Uani 1 1 d . . . . .
H8 H 1.000729 0.370567 0.446320 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8416(4) 0.47566(14) 0.42943(15) 0.0269(5) Uani 1 1 d . . . . .
H9 H 0.961458 0.505640 0.453689 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6468(4) 0.51338(13) 0.39908(13) 0.0223(5) Uani 1 1 d . . . . .
C11 C 0.4755(5) 0.46745(13) 0.36401(14) 0.0275(5) Uani 1 1 d . . . . .
H11 H 0.340668 0.491812 0.342359 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4978(4) 0.38641(14) 0.36002(14) 0.0286(5) Uani 1 1 d . . . . .
H12 H 0.376976 0.356536 0.336153 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6229(4) 0.60214(13) 0.40096(13) 0.0239(5) Uani 1 1 d . . . . .
H13 H 0.456532 0.615898 0.388778 0.029 Uiso 1 1 calc R U . . .
C14 C 0.7784(5) 0.64336(14) 0.34338(14) 0.0305(6) Uani 1 1 d . . . . .
H14 H 0.777658 0.698937 0.345072 0.037 Uiso 1 1 calc R U . . .
C15 C 0.9156(5) 0.61077(16) 0.29082(15) 0.0375(6) Uani 1 1 d . . . . .
H15A H 0.922987 0.555382 0.286607 0.045 Uiso 1 1 calc R U . . .
H15B H 1.007249 0.642619 0.257069 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6383(4) 0.63208(13) 0.63454(13) 0.0229(5) Uani 1 1 d . . . . .
C17 C 0.7997(5) 0.56099(15) 0.63749(16) 0.0339(6) Uani 1 1 d . . . . .
H17A H 0.869713 0.556876 0.689701 0.051 Uiso 1 1 calc R U . . .
H17B H 0.923982 0.566841 0.598346 0.051 Uiso 1 1 calc R U . . .
H17C H 0.709126 0.513560 0.626307 0.051 Uiso 1 1 calc R U . . .
C18 C 0.4564(4) 0.62798(15) 0.70030(14) 0.0310(5) Uani 1 1 d . . . . .
H18A H 0.536355 0.627990 0.751062 0.046 Uiso 1 1 calc R U . . .
H18B H 0.364246 0.579887 0.694908 0.046 Uiso 1 1 calc R U . . .
H18C H 0.352175 0.673445 0.697015 0.046 Uiso 1 1 calc R U . . .
C19 C 0.7735(5) 0.70906(14) 0.63642(15) 0.0287(5) Uani 1 1 d . . . . .
H19A H 0.841070 0.716716 0.688601 0.043 Uiso 1 1 calc R U . . .
H19B H 0.667013 0.752414 0.624433 0.043 Uiso 1 1 calc R U . . .
H19C H 0.899409 0.707507 0.597447 0.043 Uiso 1 1 calc R U . . .
N1 N 0.6804(3) 0.63320(12) 0.47980(11) 0.0228(4) Uani 1 1 d . . . . .
H1 H 0.816620 0.654369 0.491357 0.027 Uiso 1 1 calc R U . . .
C2 C 0.5477(5) 0.21432(15) 0.35052(19) 0.0426(7) Uani 1 1 d . . . . .
H2 H 0.421977 0.238745 0.323499 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5620(6) 0.13294(16) 0.3513(2) 0.0490(8) Uani 1 1 d . . . . .
H3 H 0.447481 0.102831 0.324475 0.059 Uiso 1 1 calc R U . . .
C4 C 0.7396(5) 0.09593(14) 0.39046(15) 0.0324(6) Uani 1 1 d . . . . .
H4 H 0.745708 0.040403 0.392599 0.039 Uiso 1 1 calc R U . . .
C5 C 0.9074(5) 0.13985(16) 0.42628(18) 0.0414(7) Uani 1 1 d . . . . .
H5 H 1.033995 0.114777 0.452251 0.050 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 1.4946(16) . ?
S1 N1 1.6603(19) . ?
S1 C16 1.841(2) . ?
C1 C6 1.385(4) . ?
C1 C2 1.394(4) . ?
C1 C7 1.497(3) . ?
C6 C5 1.396(4) . ?
C7 C8 1.394(3) . ?
C7 C12 1.394(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.390(3) . ?
C10 C13 1.523(3) . ?
C11 C12 1.392(3) . ?
C13 N1 1.485(3) . ?
C13 C14 1.501(3) . ?
C14 C15 1.315(4) . ?
C16 C19 1.525(3) . ?
C16 C17 1.525(3) . ?
C16 C18 1.532(3) . ?
C2 C3 1.393(4) . ?
C3 C4 1.369(4) . ?
C4 C5 1.362(4) . ?

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 N1 111.14(10) . . ?
O1 S1 C16 106.06(10) . . ?
N1 S1 C16 98.48(10) . . ?
C6 C1 C2 116.2(2) . . ?
C6 C1 C7 122.0(2) . . ?
C2 C1 C7 121.8(2) . . ?
C1 C6 C5 122.0(3) . . ?
C8 C7 C12 116.9(2) . . ?
C8 C7 C1 121.7(2) . . ?
C12 C7 C1 121.3(2) . . ?
C9 C8 C7 121.5(2) . . ?
C10 C9 C8 121.3(2) . . ?
C9 C10 C11 117.6(2) . . ?
C9 C10 C13 121.8(2) . . ?
C11 C10 C13 120.5(2) . . ?
C10 C11 C12 121.2(2) . . ?
C11 C12 C7 121.5(2) . . ?
N1 C13 C14 107.23(19) . . ?
N1 C13 C10 110.80(18) . . ?
C14 C13 C10 113.6(2) . . ?
C15 C14 C13 127.0(2) . . ?
C19 C16 C17 112.4(2) . . ?
C19 C16 C18 111.54(19) . . ?
C17 C16 C18 110.4(2) . . ?
C19 C16 S1 110.68(15) . . ?
C17 C16 S1 107.24(16) . . ?
C18 C16 S1 104.22(16) . . ?
C13 N1 S1 113.82(15) . . ?
C1 C2 C3 121.6(3) . . ?
C4 C3 C2 120.6(3) . . ?
C5 C4 C3 119.1(2) . . ?
C4 C5 C6 120.5(3) . . ?

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
C2 C1 C6 C5 -1.9(4) . . . . ?
C7 C1 C6 C5 177.1(3) . . . . ?
C6 C1 C7 C8 4.1(4) . . . . ?
C2 C1 C7 C8 -177.0(2) . . . . ?
C6 C1 C7 C12 -173.3(2) . . . . ?
C2 C1 C7 C12 5.6(4) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
C1 C7 C8 C9 -177.5(2) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C8 C9 C10 C13 -177.9(2) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C13 C10 C11 C12 178.3(2) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C1 C7 C12 C11 177.9(2) . . . . ?
C9 C10 C13 N1 -47.3(3) . . . . ?
C11 C10 C13 N1 134.9(2) . . . . ?
C9 C10 C13 C14 73.4(3) . . . . ?
C11 C10 C13 C14 -104.3(3) . . . . ?
N1 C13 C14 C15 127.2(3) . . . . ?
C10 C13 C14 C15 4.4(4) . . . . ?
O1 S1 C16 C19 -57.19(18) . . . . ?
N1 S1 C16 C19 57.80(17) . . . . ?
O1 S1 C16 C17 179.94(16) . . . . ?
N1 S1 C16 C17 -65.08(18) . . . . ?
O1 S1 C16 C18 62.84(17) . . . . ?
N1 S1 C16 C18 177.83(16) . . . . ?
C14 C13 N1 S1 155.87(16) . . . . ?
C10 C13 N1 S1 -79.6(2) . . . . ?
O1 S1 N1 C13 -89.71(17) . . . . ?
C16 S1 N1 C13 159.34(16) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C7 C1 C2 C3 -177.6(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
C3 C4 C5 C6 1.9(5) . . . . ?
C1 C6 C5 C4 0.3(5) . . . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_20240312LM_auto
_database_code_depnum_ccdc_archive 'CCDC 2341379'
loop_
_audit_author_name
_audit_author_address
'min liu'
;The Shanghai Jiao Tong Crystallographic Data Centre
China
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N O S'
_chemical_formula_weight         313.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.52328(9)
_cell_length_b                   10.30853(16)
_cell_length_c                   28.9172(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1646.46(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6043
_cell_measurement_theta_min      3.0460
_cell_measurement_theta_max      74.0460

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.742
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_T_max  1.562
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8412
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.056
_diffrn_reflns_theta_max         75.259
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3084
_reflns_number_gt                2966
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_max     0.837
_reflns_Friedel_fraction_full    0.912

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0557P)²+0.4292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3084
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
C2 C 0.1250(5) 0.3831(3) 0.57413(9) 0.0299(6) Uani 1 1 d . . . . .
H2 H -0.006260 0.441780 0.570369 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1202(5) 0.2945(3) 0.61016(9) 0.0310(6) Uani 1 1 d . . . . .
H3 H -0.013523 0.293933 0.630832 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3059(5) 0.2073(3) 0.61647(9) 0.0272(6) Uani 1 1 d . . . . .
H4 H 0.301701 0.146680 0.641194 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4988(6) 0.2099(3) 0.58602(10) 0.0364(7) Uani 1 1 d . . . . .
H5 H 0.628821 0.150588 0.589811 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5037(5) 0.2989(3) 0.54986(9) 0.0322(6) Uani 1 1 d . . . . .
H6 H 0.637258 0.298624 0.529149 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3235(4) 0.4836(2) 0.50454(8) 0.0181(5) Uani 1 1 d . . . . .
C8 C 0.5094(6) 0.4843(3) 0.47236(9) 0.0391(8) Uani 1 1 d . . . . .
H8 H 0.638757 0.424280 0.475584 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5113(5) 0.5704(3) 0.43564(9) 0.0386(7) Uani 1 1 d . . . . .
H9 H 0.641446 0.567840 0.414183 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3284(4) 0.6599(2) 0.42951(7) 0.0181(4) Uani 1 1 d . . . . .
C11 C 0.1455(5) 0.6618(3) 0.46190(10) 0.0400(7) Uani 1 1 d . . . . .
H11 H 0.017993 0.723108 0.459041 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1454(6) 0.5752(3) 0.49866(11) 0.0418(8) Uani 1 1 d . . . . .
H12 H 0.017482 0.579419 0.520570 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3333(4) 0.7498(2) 0.38744(7) 0.0187(5) Uani 1 1 d . . . . .
H13 H 0.498712 0.788986 0.386098 0.022 Uiso 1 1 calc R U . . .
C14 C 0.1553(4) 0.8605(2) 0.39057(8) 0.0199(5) Uani 1 1 d . . . . .
H14 H 0.153156 0.908736 0.418556 0.024 Uiso 1 1 calc R U . . .
C15 C 0.0017(5) 0.8964(2) 0.35780(8) 0.0268(6) Uani 1 1 d . . . . .
H15A H -0.002491 0.850882 0.329242 0.032 Uiso 1 1 calc R U . . .
H15B H -0.104142 0.967582 0.362861 0.032 Uiso 1 1 calc R U . . .
C16 C 0.3738(4) 0.5764(2) 0.26167(8) 0.0171(4) Uani 1 1 d . . . . .
C17 C 0.2596(5) 0.4502(2) 0.27883(8) 0.0225(5) Uani 1 1 d . . . . .
H17A H 0.214869 0.396218 0.252279 0.034 Uiso 1 1 calc R U . . .
H17B H 0.114641 0.470116 0.297025 0.034 Uiso 1 1 calc R U . . .
H17C H 0.376201 0.403407 0.298176 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5729(4) 0.5474(2) 0.22606(8) 0.0213(5) Uani 1 1 d . . . . .
H18A H 0.500651 0.506974 0.198663 0.032 Uiso 1 1 calc R U . . .
H18B H 0.692166 0.488251 0.239652 0.032 Uiso 1 1 calc R U . . .
H18C H 0.652870 0.628486 0.217130 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1890(4) 0.6707(2) 0.24152(8) 0.0215(5) Uani 1 1 d . . . . .
H19A H 0.123726 0.635200 0.212656 0.032 Uiso 1 1 calc R U . . .
H19B H 0.267517 0.754127 0.235262 0.032 Uiso 1 1 calc R U . . .
H19C H 0.056862 0.683400 0.263689 0.032 Uiso 1 1 calc R U . . .
S1 S 0.53568(10) 0.65907(5) 0.30943(2) 0.01634(15) Uani 1 1 d . . . . .
O1 O 0.7157(3) 0.56302(17) 0.32655(5) 0.0236(4) Uani 1 1 d . . . . .
N1 N 0.2996(4) 0.67563(19) 0.34435(6) 0.0181(4) Uani 1 1 d . . . . .
H1 H 0.204(6) 0.611(3) 0.3475(10) 0.027 Uiso 1 1 d . U . . .
C1 C 0.3190(4) 0.3878(2) 0.54327(7) 0.0186(5) 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
C2 C3 1.386(4) . ?
C2 C1 1.395(3) . ?
C3 C4 1.376(4) . ?
C4 C5 1.382(4) . ?
C5 C6 1.391(4) . ?
C6 C1 1.385(3) . ?
C7 C12 1.374(4) . ?
C7 C8 1.386(3) . ?
C7 C1 1.493(3) . ?
C8 C9 1.384(4) . ?
C9 C10 1.379(4) . ?
C10 C11 1.378(3) . ?
C10 C13 1.529(3) . ?
C11 C12 1.388(4) . ?
C13 N1 1.474(3) . ?
C13 C14 1.509(3) . ?
C14 C15 1.324(3) . ?
C16 C19 1.526(3) . ?
C16 C17 1.528(3) . ?
C16 C18 1.536(3) . ?
C16 S1 1.853(2) . ?
S1 O1 1.4879(17) . ?
S1 N1 1.6581(19) . ?

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 C1 121.2(3) . . ?
C4 C3 C2 121.1(2) . . ?
C3 C4 C5 118.5(2) . . ?
C4 C5 C6 120.5(3) . . ?
C1 C6 C5 121.7(3) . . ?
C12 C7 C8 116.3(2) . . ?
C12 C7 C1 122.3(2) . . ?
C8 C7 C1 121.3(2) . . ?
C9 C8 C7 121.6(3) . . ?
C10 C9 C8 121.5(2) . . ?
C11 C10 C9 117.3(2) . . ?
C11 C10 C13 123.0(2) . . ?
C9 C10 C13 119.6(2) . . ?
C10 C11 C12 120.8(3) . . ?
C7 C12 C11 122.4(2) . . ?
N1 C13 C14 111.14(18) . . ?
N1 C13 C10 110.86(19) . . ?
C14 C13 C10 113.52(18) . . ?
C15 C14 C13 125.8(2) . . ?
C19 C16 C17 113.0(2) . . ?
C19 C16 C18 110.30(18) . . ?
C17 C16 C18 110.33(19) . . ?
C19 C16 S1 108.34(15) . . ?
C17 C16 S1 110.41(16) . . ?
C18 C16 S1 104.11(15) . . ?
O1 S1 N1 113.03(10) . . ?
O1 S1 C16 105.33(10) . . ?
N1 S1 C16 97.00(10) . . ?
C13 N1 S1 117.98(16) . . ?
C6 C1 C2 117.1(2) . . ?
C6 C1 C7 121.9(2) . . ?
C2 C1 C7 121.0(2) . . ?

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
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C12 C7 C8 C9 -1.8(4) . . . . ?
C1 C7 C8 C9 178.2(3) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C8 C9 C10 C13 -177.8(3) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C13 C10 C11 C12 177.8(3) . . . . ?
C8 C7 C12 C11 1.9(5) . . . . ?
C1 C7 C12 C11 -178.0(3) . . . . ?
C10 C11 C12 C7 -0.5(5) . . . . ?
C11 C10 C13 N1 -112.2(3) . . . . ?
C9 C10 C13 N1 66.7(3) . . . . ?
C11 C10 C13 C14 13.8(3) . . . . ?
C9 C10 C13 C14 -167.4(2) . . . . ?
N1 C13 C14 C15 -5.8(3) . . . . ?
C10 C13 C14 C15 -131.6(2) . . . . ?
C19 C16 S1 O1 -178.71(15) . . . . ?
C17 C16 S1 O1 57.10(18) . . . . ?
C18 C16 S1 O1 -61.31(16) . . . . ?
C19 C16 S1 N1 65.04(17) . . . . ?
C17 C16 S1 N1 -59.15(17) . . . . ?
C18 C16 S1 N1 -177.56(15) . . . . ?
C14 C13 N1 S1 123.74(18) . . . . ?
C10 C13 N1 S1 -109.01(19) . . . . ?
O1 S1 N1 C13 75.45(19) . . . . ?
C16 S1 N1 C13 -174.58(17) . . . . ?
C5 C6 C1 C2 -1.0(4) . . . . ?
C5 C6 C1 C7 180.0(3) . . . . ?
C3 C2 C1 C6 1.0(4) . . . . ?
C3 C2 C1 C7 -179.9(2) . . . . ?
C12 C7 C1 C6 -177.7(3) . . . . ?
C8 C7 C1 C6 2.4(4) . . . . ?
C12 C7 C1 C2 3.3(4) . . . . ?
C8 C7 C1 C2 -176.6(3) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.042



