# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2g3jhm
_database_code_depnum_ccdc_archive 'CCDC 2267510'
loop_
_audit_author_name
_audit_author_address
hqw
;shanghai university
China
;
_audit_update_record             
;
2023-06-05 deposited with the CCDC.	2023-12-04 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          138
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O3'
_chemical_formula_weight         372.41

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'

_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                   9.1943(4)
_cell_length_b                   14.3898(6)
_cell_length_c                   14.7328(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1949.21(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    256(2)
_cell_measurement_reflns_used    3100
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.685
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      256(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            21328
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.672
_diffrn_reflns_theta_max         66.831
_diffrn_reflns_theta_full        66.831
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3427
_reflns_number_gt                3186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.995
_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    ?
_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)+(0.0750P)²+0.0899P] 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 1308 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3427
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C1 C 0.2078(3) 0.65316(17) 0.35549(15) 0.0353(5) Uani 1 1 d . . . . .
C2 C 0.2378(3) 0.74728(17) 0.35502(16) 0.0349(5) Uani 1 1 d . . . . .
C3 C 0.2509(3) 0.77826(17) 0.44707(16) 0.0356(5) Uani 1 1 d . . . . .
H3 H 0.271801 0.838560 0.465673 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2275(3) 0.70421(17) 0.50251(16) 0.0332(5) Uani 1 1 d . . . . .
C5 C 0.2337(3) 0.69724(16) 0.60230(16) 0.0343(5) Uani 1 1 d . . . . .
C6 C 0.1229(3) 0.6577(2) 0.65284(18) 0.0431(6) Uani 1 1 d . . . . .
H6 H 0.042270 0.632415 0.623772 0.052 Uiso 1 1 calc R U . . .
C7 C 0.1321(4) 0.6557(2) 0.74710(19) 0.0516(8) Uani 1 1 d . . . . .
H7 H 0.056876 0.629901 0.781020 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2529(4) 0.6919(2) 0.79041(18) 0.0502(7) Uani 1 1 d . . . . .
H8 H 0.260025 0.689403 0.853332 0.060 Uiso 1 1 calc R U . . .
C9 C 0.3620(4) 0.7316(3) 0.7403(2) 0.0538(8) Uani 1 1 d . . . . .
H9 H 0.442526 0.756861 0.769440 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3534(3) 0.7342(2) 0.64659(19) 0.0452(7) Uani 1 1 d . . . . .
H10 H 0.428309 0.760979 0.613157 0.054 Uiso 1 1 calc R U . . .
C11 C 0.1837(4) 0.5843(2) 0.28230(17) 0.0475(7) Uani 1 1 d . . . . .
H11A H 0.193824 0.614139 0.224366 0.071 Uiso 1 1 calc R U . . .
H11B H 0.254098 0.535287 0.287422 0.071 Uiso 1 1 calc R U . . .
H11C H 0.087613 0.558800 0.287671 0.071 Uiso 1 1 calc R U . . .
C12 C 0.2446(3) 0.80579(18) 0.27384(17) 0.0383(6) Uani 1 1 d . . . . .
C13 C 0.2652(5) 0.9604(2) 0.2207(2) 0.0610(9) Uani 1 1 d . . . . .
H13A H 0.166286 0.972548 0.201250 0.073 Uiso 1 1 calc R U . . .
H13B H 0.318967 0.934992 0.169800 0.073 Uiso 1 1 calc R U . . .
C14 C 0.3347(7) 1.0477(2) 0.2526(3) 0.0845(14) Uani 1 1 d . . . . .
H14A H 0.335841 1.092224 0.204044 0.127 Uiso 1 1 calc R U . . .
H14B H 0.280560 1.072411 0.302825 0.127 Uiso 1 1 calc R U . . .
H14C H 0.432631 1.035005 0.271501 0.127 Uiso 1 1 calc R U . . .
C15 C 0.0464(3) 0.50168(18) 0.48225(17) 0.0375(6) Uani 1 1 d . . . . .
C16 C 0.0417(3) 0.40708(19) 0.51746(18) 0.0424(6) Uani 1 1 d . . . . .
H16 H -0.048333 0.378732 0.525229 0.051 Uiso 1 1 calc R U . . .
C17 C 0.1617(3) 0.35940(18) 0.53904(16) 0.0400(6) Uani 1 1 d . . . . .
H17 H 0.152470 0.299604 0.562286 0.048 Uiso 1 1 calc R U . . .
C18 C 0.3039(3) 0.39801(17) 0.52728(14) 0.0341(5) Uani 1 1 d . . . . .
C19 C 0.3167(3) 0.48954(17) 0.49515(14) 0.0322(5) Uani 1 1 d . . . . .
C20 C 0.4529(3) 0.53063(19) 0.48383(17) 0.0393(6) Uani 1 1 d . . . . .
H20 H 0.460703 0.591415 0.462954 0.047 Uiso 1 1 calc R U . . .
C21 C 0.5761(3) 0.4797(2) 0.50410(19) 0.0451(6) Uani 1 1 d . . . . .
H21 H 0.667298 0.506774 0.497183 0.054 Uiso 1 1 calc R U . . .
C22 C 0.5659(3) 0.3885(2) 0.53466(19) 0.0462(7) Uani 1 1 d . . . . .
H22 H 0.649814 0.354717 0.547008 0.055 Uiso 1 1 calc R U . . .
C23 C 0.4322(3) 0.34841(18) 0.54659(17) 0.0412(6) Uani 1 1 d . . . . .
H23 H 0.426023 0.287641 0.567725 0.049 Uiso 1 1 calc R U . . .
N1 N 0.1998(2) 0.62887(13) 0.44579(13) 0.0337(4) Uani 1 1 d . . . . .
N2 N 0.1877(2) 0.53763(14) 0.47547(13) 0.0333(4) Uani 1 1 d . . . . .
O1 O 0.2316(3) 0.77893(15) 0.19665(13) 0.0543(6) Uani 1 1 d . . . . .
O2 O 0.2656(2) 0.89509(13) 0.29576(12) 0.0464(5) Uani 1 1 d . . . . .
O3 O -0.0588(2) 0.54786(14) 0.46114(14) 0.0480(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
C1 N1 1.378(3) . ?
C1 C2 1.382(4) . ?
C1 C11 1.481(3) . ?
C2 C3 1.433(3) . ?
C2 C12 1.464(3) . ?
C3 C4 1.360(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.392(3) . ?
C4 C5 1.475(3) . ?
C5 C6 1.384(4) . ?
C5 C10 1.386(4) . ?
C6 C7 1.392(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O1 1.207(3) . ?
C12 O2 1.339(3) . ?
C13 O2 1.451(3) . ?
C13 C14 1.486(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O3 1.214(3) . ?
C15 N2 1.402(4) . ?
C15 C16 1.457(4) . ?
C16 C17 1.337(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.431(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.405(3) . ?
C18 C23 1.408(4) . ?
C19 C20 1.395(4) . ?
C19 N2 1.403(3) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N1 N2 1.388(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
N1 C1 C2 105.3(2) . . ?
N1 C1 C11 121.7(2) . . ?
C2 C1 C11 133.0(2) . . ?
C1 C2 C3 108.5(2) . . ?
C1 C2 C12 125.2(2) . . ?
C3 C2 C12 126.2(2) . . ?
C4 C3 C2 108.1(2) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
C3 C4 N1 106.2(2) . . ?
C3 C4 C5 130.2(2) . . ?
N1 C4 C5 123.5(2) . . ?
C6 C5 C10 119.3(2) . . ?
C6 C5 C4 122.4(2) . . ?
C10 C5 C4 118.3(2) . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 O2 123.3(2) . . ?
O1 C12 C2 125.5(2) . . ?
O2 C12 C2 111.2(2) . . ?
O2 C13 C14 107.8(3) . . ?
O2 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
O2 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 N2 121.2(2) . . ?
O3 C15 C16 125.4(3) . . ?
N2 C15 C16 113.4(2) . . ?
C17 C16 C15 122.6(3) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C23 118.3(2) . . ?
C19 C18 C17 118.8(2) . . ?
C23 C18 C17 123.0(2) . . ?
C20 C19 N2 121.7(2) . . ?
C20 C19 C18 120.9(2) . . ?
N2 C19 C18 117.5(2) . . ?
C21 C20 C19 119.0(3) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C18 120.9(2) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C1 N1 N2 123.3(2) . . ?
C1 N1 C4 111.85(19) . . ?
N2 N1 C4 124.20(19) . . ?
N1 N2 C15 116.5(2) . . ?
N1 N2 C19 117.63(19) . . ?
C15 N2 C19 125.9(2) . . ?
C12 O2 C13 116.0(2) . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MEOH/HEXANE'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2267692'
loop_
_audit_author_name
_audit_author_address
hqw
;shanghai university
China
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-12-04 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            'C20 H17 N3 O3 S'
_chemical_formula_weight         379.42

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.3762(12)
_cell_length_b                   9.0242(15)
_cell_length_c                   13.612(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.049(5)
_cell_angle_gamma                90
_cell_volume                     886.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    211(2)
_cell_measurement_reflns_used    2800
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.853
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_T_max  0.629
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      211(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            9166
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.320
_diffrn_reflns_theta_max         66.782
_diffrn_reflns_theta_full        66.782
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2955
_reflns_number_gt                2910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.989

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0954P)²+0.5801P] 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 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2955
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.29013(15) 0.58416(15) 0.83640(8) 0.0315(3) Uani 1 1 d . . . . .
O3 O 1.1149(4) 0.1999(4) 0.7363(2) 0.0273(7) Uani 1 1 d . . . . .
O1 O 0.7262(5) 0.7730(4) 0.7879(3) 0.0328(8) Uani 1 1 d . . . . .
O2 O 1.0271(4) 0.1035(4) 0.8710(2) 0.0308(8) Uani 1 1 d . . . . .
N2 N 0.5528(4) 0.5907(4) 0.6978(2) 0.0170(7) Uani 1 1 d . . . . .
N1 N 0.6577(5) 0.4833(4) 0.7555(3) 0.0175(7) Uani 1 1 d . . . . .
N3 N 0.3310(5) 0.8070(4) 0.5883(3) 0.0241(8) Uani 1 1 d . . . . .
C7 C 0.4051(5) 0.3646(5) 0.9669(3) 0.0183(9) Uani 1 1 d . . . . .
H7 H 0.471545 0.285620 1.002480 0.022 Uiso 1 1 calc R U . . .
C1 C 0.6028(5) 0.4065(4) 0.8335(3) 0.0181(8) Uani 1 1 d . . . . .
C13 C 0.4139(6) 0.5455(5) 0.6164(3) 0.0176(8) Uani 1 1 d . . . . .
C4 C 0.8092(5) 0.4194(5) 0.7289(3) 0.0179(8) Uani 1 1 d . . . . .
C14 C 0.3844(6) 0.3983(5) 0.5908(3) 0.0217(9) Uani 1 1 d . . . . .
H14 H 0.457042 0.324061 0.628456 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5958(6) 0.7387(5) 0.7224(3) 0.0198(8) Uani 1 1 d . . . . .
C2 C 0.7279(6) 0.2929(5) 0.8578(3) 0.0206(9) Uani 1 1 d . . . . .
H2 H 0.728432 0.221766 0.908271 0.025 Uiso 1 1 calc R U . . .
C5 C 0.8913(6) 0.4847(5) 0.6487(3) 0.0210(9) Uani 1 1 d . . . . .
H5A H 0.996546 0.425546 0.639950 0.032 Uiso 1 1 calc R U . . .
H5B H 0.799286 0.486520 0.586342 0.032 Uiso 1 1 calc R U . . .
H5C H 0.931970 0.585023 0.667176 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3054(6) 0.6583(5) 0.5621(3) 0.0207(9) Uani 1 1 d . . . . .
C19 C 1.0134(6) 0.2004(5) 0.7946(3) 0.0212(9) Uani 1 1 d . . . . .
C11 C 0.4642(6) 0.8449(4) 0.6615(3) 0.0230(9) Uani 1 1 d . . . . .
C9 C 0.1665(6) 0.5476(5) 0.9256(3) 0.0286(10) Uani 1 1 d . . . . .
H9 H 0.059568 0.600482 0.931590 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2454(6) 0.3611(5) 0.5085(3) 0.0276(10) Uani 1 1 d . . . . .
H15 H 0.224351 0.261179 0.490027 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8565(5) 0.3012(5) 0.7934(3) 0.0187(9) Uani 1 1 d . . . . .
C17 C 0.1657(6) 0.6174(5) 0.4795(3) 0.0251(10) Uani 1 1 d . . . . .
H17 H 0.091310 0.690792 0.442067 0.030 Uiso 1 1 calc R U . . .
C16 C 0.1373(6) 0.4717(6) 0.4534(3) 0.0295(11) Uani 1 1 d . . . . .
H16 H 0.044093 0.445885 0.397733 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4470(5) 0.4447(5) 0.8783(3) 0.0188(8) Uani 1 1 d . . . . .
C8 C 0.2360(6) 0.4368(6) 0.9862(3) 0.0294(10) Uani 1 1 d . . . . .
H8 H 0.180258 0.405814 1.038859 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4945(8) 1.0050(5) 0.6893(5) 0.0369(13) Uani 1 1 d . . . . .
H18A H 0.599317 1.014208 0.745368 0.055 Uiso 1 1 calc R U . . .
H18B H 0.519297 1.059891 0.632266 0.055 Uiso 1 1 calc R U . . .
H18C H 0.384402 1.044606 0.708268 0.055 Uiso 1 1 calc R U . . .
C20 C 1.1721(9) -0.0061(7) 0.8773(5) 0.0462(15) Uani 1 1 d . . . . .
H20A H 1.171744 -0.070748 0.934125 0.069 Uiso 1 1 calc R U . . .
H20B H 1.150539 -0.064208 0.815981 0.069 Uiso 1 1 calc R U . . .
H20C H 1.291153 0.043299 0.885822 0.069 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 C9 1.696(5) . ?
S1 C6 1.724(4) . ?
O3 C19 1.199(5) . ?
O1 C10 1.207(6) . ?
O2 C19 1.347(5) . ?
O2 C20 1.445(6) . ?
N2 N1 1.379(5) . ?
N2 C10 1.398(6) . ?
N2 C13 1.404(5) . ?
N1 C4 1.371(5) . ?
N1 C1 1.397(5) . ?
N3 C11 1.291(6) . ?
N3 C12 1.391(6) . ?
C7 C8 1.479(6) . ?
C7 C6 1.492(6) . ?
C1 C2 1.373(6) . ?
C1 C6 1.451(6) . ?
C13 C14 1.379(6) . ?
C13 C12 1.405(6) . ?
C4 C3 1.380(6) . ?
C4 C5 1.477(6) . ?
C14 C15 1.393(6) . ?
C10 C11 1.487(6) . ?
C2 C3 1.420(6) . ?
C12 C17 1.406(6) . ?
C19 C3 1.470(6) . ?
C11 C18 1.498(6) . ?
C9 C8 1.329(7) . ?
C15 C16 1.395(7) . ?
C17 C16 1.366(7) . ?

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
C9 S1 C6 92.6(2) . . ?
C19 O2 C20 115.2(4) . . ?
N1 N2 C10 117.6(3) . . ?
N1 N2 C13 118.4(3) . . ?
C10 N2 C13 124.0(3) . . ?
C4 N1 N2 122.4(3) . . ?
C4 N1 C1 112.0(3) . . ?
N2 N1 C1 124.4(3) . . ?
C11 N3 C12 119.6(4) . . ?
C8 C7 C6 104.8(4) . . ?
C2 C1 N1 105.4(3) . . ?
C2 C1 C6 128.9(4) . . ?
N1 C1 C6 125.6(4) . . ?
C14 C13 N2 122.0(4) . . ?
C14 C13 C12 121.5(4) . . ?
N2 C13 C12 116.5(4) . . ?
N1 C4 C3 105.6(4) . . ?
N1 C4 C5 120.7(4) . . ?
C3 C4 C5 133.7(4) . . ?
C13 C14 C15 119.1(4) . . ?
O1 C10 N2 121.8(4) . . ?
O1 C10 C11 125.0(4) . . ?
N2 C10 C11 113.2(4) . . ?
C1 C2 C3 108.3(4) . . ?
N3 C12 C13 122.1(4) . . ?
N3 C12 C17 119.7(4) . . ?
C13 C12 C17 118.1(4) . . ?
O3 C19 O2 123.5(4) . . ?
O3 C19 C3 126.5(4) . . ?
O2 C19 C3 110.1(4) . . ?
N3 C11 C10 124.2(4) . . ?
N3 C11 C18 120.0(4) . . ?
C10 C11 C18 115.8(4) . . ?
C8 C9 S1 113.3(4) . . ?
C14 C15 C16 120.1(4) . . ?
C4 C3 C2 108.7(4) . . ?
C4 C3 C19 125.4(4) . . ?
C2 C3 C19 125.9(4) . . ?
C16 C17 C12 120.5(4) . . ?
C17 C16 C15 120.6(4) . . ?
C1 C6 C7 122.7(3) . . ?
C1 C6 S1 124.8(3) . . ?
C7 C6 S1 112.5(3) . . ?
C9 C8 C7 116.8(4) . . ?

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.093



