# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_exp_12244
_database_code_depnum_ccdc_archive 'CCDC 2128019'
loop_
_audit_author_name
_audit_author_address
Chixiaochen
;Shandong University of Technology
China
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-04-15 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            'C H N O S'
_chemical_formula_weight         75.09

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           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                   5.9586(3)
_cell_length_b                   24.1571(16)
_cell_length_c                   14.4415(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.636(5)
_cell_angle_gamma                90
_cell_volume                     2068.7(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.060
_exptl_crystal_F_000             38
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7201
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.578
_diffrn_reflns_theta_max         69.973
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3862
_reflns_number_gt                2433
_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       ?
_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)+(0.0605P)²+60.1277P] 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         3862
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1908
_refine_ls_R_factor_gt           0.1340
_refine_ls_wR_factor_ref         0.4887
_refine_ls_wR_factor_gt          0.4698
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.367
_refine_ls_shift/su_mean         0.031

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 0.5450(6) 1.04720(16) 0.8041(3) 0.0561(10) Uani 1 1 d . . . . .
O1 O 0.7169(15) 1.0422(5) 0.7430(8) 0.068(3) Uani 1 1 d . . . . .
N1 N 0.4014(18) 0.9887(5) 0.7968(7) 0.048(3) Uani 1 1 d . . . . .
C11 C 0.1642(16) 0.9359(5) 0.6808(8) 0.034(3) Uani 1 1 d . . . . .
C18 C 0.0406(16) 0.8477(5) 0.7494(9) 0.040(3) Uani 1 1 d . . . . .
C10 C 0.0242(17) 0.9107(5) 0.7525(8) 0.034(3) Uani 1 1 d . . . . .
H10 H -0.132820 0.923271 0.743495 0.041 Uiso 1 1 calc R U . . .
O2 O 0.600(2) 1.0568(5) 0.9017(7) 0.079(4) Uani 1 1 d . . . . .
C13 C 0.105(2) 0.9204(6) 0.5804(9) 0.048(3) Uani 1 1 d . . . . .
H13A H -0.052562 0.929435 0.564164 0.058 Uiso 1 1 calc R U . . .
H13B H 0.119693 0.880601 0.575149 0.058 Uiso 1 1 calc R U . . .
C8 C 0.231(2) 0.9805(6) 0.8627(9) 0.048(3) Uani 1 1 d . . . . .
H8A H 0.111479 1.007612 0.850659 0.058 Uiso 1 1 calc R U . . .
H8B H 0.299422 0.985920 0.925740 0.058 Uiso 1 1 calc R U . . .
C12 C 0.331(2) 0.9698(5) 0.7043(9) 0.043(3) Uani 1 1 d . . . . .
H12 H 0.412105 0.982757 0.656745 0.052 Uiso 1 1 calc R U . . .
C9 C 0.132(2) 0.9227(5) 0.8532(8) 0.041(3) Uani 1 1 d . . . . .
C3 C 0.184(3) 1.1514(6) 0.6322(11) 0.059(4) Uani 1 1 d . . . . .
H3 H 0.180471 1.161629 0.569915 0.071 Uiso 1 1 calc R U . . .
C20 C -0.013(3) 0.7639(6) 0.6475(11) 0.057(4) Uani 1 1 d . . . . .
H20 H 0.131198 0.752342 0.670368 0.069 Uiso 1 1 calc R U . . .
C15 C -0.048(2) 0.9193(6) 0.9210(9) 0.056(4) Uani 1 1 d . . . . .
H15A H 0.019782 0.925492 0.983142 0.084 Uiso 1 1 calc R U . . .
H15B H -0.116853 0.883342 0.917064 0.084 Uiso 1 1 calc R U . . .
H15C H -0.161152 0.947044 0.905350 0.084 Uiso 1 1 calc R U . . .
C5 C 0.354(2) 1.0990(6) 0.7611(9) 0.045(3) Uani 1 1 d . . . . .
C19 C -0.0975(18) 0.8132(5) 0.6802(9) 0.041(3) Uani 1 1 d . . . . .
C17 C 0.1974(18) 0.8292(6) 0.8137(10) 0.052(4) Uani 1 1 d . . . . .
H17 H 0.236749 0.792088 0.821531 0.062 Uiso 1 1 calc R U . . .
C2 C 0.032(2) 1.1738(6) 0.6858(11) 0.055(4) Uani 1 1 d . . . . .
C7 C 0.043(3) 1.1582(7) 0.7791(12) 0.067(4) Uani 1 1 d . . . . .
H7 H -0.060294 1.173002 0.816746 0.080 Uiso 1 1 calc R U . . .
C4 C 0.344(2) 1.1140(6) 0.6682(10) 0.054(3) Uani 1 1 d . . . . .
H4 H 0.445490 1.098861 0.630164 0.065 Uiso 1 1 calc R U . . .
C6 C 0.202(3) 1.1213(7) 0.8164(10) 0.062(4) Uani 1 1 d . . . . .
H6 H 0.206620 1.111437 0.878832 0.075 Uiso 1 1 calc R U . . .
C22 C -0.349(3) 0.7481(7) 0.5483(11) 0.067(4) Uani 1 1 d . . . . .
H22 H -0.431582 0.726855 0.503362 0.080 Uiso 1 1 calc R U . . .
C1 C -0.144(2) 1.2136(8) 0.6462(15) 0.086(6) Uani 1 1 d . . . . .
H1A H -0.103358 1.227751 0.588059 0.130 Uiso 1 1 calc R U . . .
H1B H -0.155875 1.243716 0.688915 0.130 Uiso 1 1 calc R U . . .
H1C H -0.286852 1.194958 0.636284 0.130 Uiso 1 1 calc R U . . .
C14 C 0.240(3) 0.9469(7) 0.5091(10) 0.068(4) Uani 1 1 d . . . . .
H14A H 0.224760 0.986401 0.511792 0.102 Uiso 1 1 calc R U . . .
H14B H 0.185244 0.934067 0.448087 0.102 Uiso 1 1 calc R U . . .
H14C H 0.396088 0.937014 0.521933 0.102 Uiso 1 1 calc R U . . .
C23 C -0.439(2) 0.7957(7) 0.5808(11) 0.058(4) Uani 1 1 d . . . . .
H23 H -0.584804 0.806286 0.559491 0.070 Uiso 1 1 calc R U . . .
C24 C -0.312(2) 0.8281(6) 0.6456(9) 0.051(3) Uani 1 1 d . . . . .
H24 H -0.372915 0.860781 0.666142 0.061 Uiso 1 1 calc R U . . .
C21 C -0.136(3) 0.7320(7) 0.5820(11) 0.069(4) Uani 1 1 d . . . . .
H21 H -0.075705 0.699412 0.560846 0.083 Uiso 1 1 calc R U . . .
C16 C 0.304(2) 0.8755(6) 0.8722(10) 0.052(4) Uani 1 1 d . . . . .
H16A H 0.449421 0.885549 0.852812 0.062 Uiso 1 1 calc R U . . .
H16B H 0.321092 0.865624 0.937608 0.062 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 1.422(11) . ?
S1 O2 1.433(11) . ?
S1 N1 1.651(11) . ?
S1 C5 1.763(15) . ?
N1 C12 1.435(16) . ?
N1 C8 1.472(17) . ?
C11 C12 1.308(16) . ?
C11 C13 1.505(17) . ?
C11 C10 1.519(15) . ?
C18 C17 1.329(17) . ?
C18 C19 1.486(17) . ?
C18 C10 1.526(17) . ?
C10 C9 1.557(16) . ?
C10 H10 0.9800 . ?
C13 C14 1.511(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C8 C9 1.516(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12 0.9300 . ?
C9 C15 1.524(18) . ?
C9 C16 1.538(18) . ?
C3 C2 1.36(2) . ?
C3 C4 1.38(2) . ?
C3 H3 0.9300 . ?
C20 C21 1.38(2) . ?
C20 C19 1.394(18) . ?
C20 H20 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C5 C6 1.38(2) . ?
C5 C4 1.386(18) . ?
C19 C24 1.372(18) . ?
C17 C16 1.504(19) . ?
C17 H17 0.9300 . ?
C2 C7 1.40(2) . ?
C2 C1 1.50(2) . ?
C7 C6 1.37(2) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C22 C23 1.37(2) . ?
C22 C21 1.37(2) . ?
C22 H22 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C23 C24 1.386(19) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C21 H21 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 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
O1 S1 O2 121.0(7) . . ?
O1 S1 N1 106.8(6) . . ?
O2 S1 N1 105.6(6) . . ?
O1 S1 C5 108.7(6) . . ?
O2 S1 C5 107.9(7) . . ?
N1 S1 C5 105.9(6) . . ?
C12 N1 C8 113.8(10) . . ?
C12 N1 S1 115.7(9) . . ?
C8 N1 S1 117.4(9) . . ?
C12 C11 C13 120.3(11) . . ?
C12 C11 C10 122.0(11) . . ?
C13 C11 C10 117.7(10) . . ?
C17 C18 C19 125.8(12) . . ?
C17 C18 C10 111.0(11) . . ?
C19 C18 C10 123.2(10) . . ?
C11 C10 C18 109.7(10) . . ?
C11 C10 C9 111.0(9) . . ?
C18 C10 C9 101.0(9) . . ?
C11 C10 H10 111.5 . . ?
C18 C10 H10 111.6 . . ?
C9 C10 H10 111.5 . . ?
C11 C13 C14 117.5(11) . . ?
C11 C13 H13A 107.9 . . ?
C14 C13 H13A 107.9 . . ?
C11 C13 H13B 107.9 . . ?
C14 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
N1 C8 C9 110.6(11) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C11 C12 N1 125.7(12) . . ?
C11 C12 H12 117.2 . . ?
N1 C12 H12 117.1 . . ?
C8 C9 C15 106.5(11) . . ?
C8 C9 C16 114.8(10) . . ?
C15 C9 C16 110.1(11) . . ?
C8 C9 C10 112.1(10) . . ?
C15 C9 C10 109.8(10) . . ?
C16 C9 C10 103.6(10) . . ?
C2 C3 C4 121.4(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C21 C20 C19 121.5(14) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.2 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C5 C4 119.5(14) . . ?
C6 C5 S1 120.8(11) . . ?
C4 C5 S1 119.5(11) . . ?
C24 C19 C20 117.2(13) . . ?
C24 C19 C18 122.0(12) . . ?
C20 C19 C18 120.8(11) . . ?
C18 C17 C16 111.7(12) . . ?
C18 C17 H17 124.2 . . ?
C16 C17 H17 124.2 . . ?
C3 C2 C7 118.2(14) . . ?
C3 C2 C1 121.4(16) . . ?
C7 C2 C1 120.4(15) . . ?
C6 C7 C2 121.3(15) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.4 . . ?
C3 C4 C5 120.0(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C6 C7 119.7(15) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.2 . . ?
C23 C22 C21 119.7(14) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.4 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C22 C23 C24 119.9(14) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 121.6(14) . . ?
C19 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C20 C21 C22 120.0(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C16 C9 102.5(10) . . ?
C17 C16 H16A 111.2 . . ?
C9 C16 H16A 111.3 . . ?
C17 C16 H16B 111.3 . . ?
C9 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?

_refine_diff_density_max         0.681
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_exp_12248
_database_code_depnum_ccdc_archive 'CCDC 2128020'
loop_
_audit_author_name
_audit_author_address
'Xiaochen Chi'
;Shandong University of Technology
China
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-04-15 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            'C H N O S'
_chemical_formula_weight         75.09

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           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                   12.2775(5)
_cell_length_b                   16.5882(6)
_cell_length_c                   11.0592(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.497(3)
_cell_angle_gamma                90
_cell_volume                     2221.46(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.056
_exptl_crystal_F_000             38
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.249
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8246
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.521
_diffrn_reflns_theta_max         69.987
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4179
_reflns_number_gt                3151
_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       ?
_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)+(0.1924P)²+1.5594P] 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         4179
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1541
_refine_ls_goodness_of_fit_ref   0.670
_refine_ls_restrained_S_all      0.670
_refine_ls_shift/su_max          0.773
_refine_ls_shift/su_mean         0.021

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 0.66456(5) 0.22755(3) 0.11451(5) 0.0422(2) Uani 1 1 d . . . . .
O1 O 0.66195(17) 0.18746(11) 0.22857(17) 0.0546(5) Uani 1 1 d . . . . .
O2 O 0.65881(17) 0.18237(11) 0.00341(17) 0.0553(5) Uani 1 1 d . . . . .
N1 N 0.78090(16) 0.27741(12) 0.13078(17) 0.0403(5) Uani 1 1 d . . . . .
C1 C 0.80850(19) 0.32770(14) 0.23587(19) 0.0378(5) Uani 1 1 d . . . . .
H1 H 0.762209 0.327949 0.294489 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5581(2) 0.29948(15) 0.0937(2) 0.0413(5) Uani 1 1 d . . . . .
C3 C 0.8205(2) 0.30921(16) 0.0220(2) 0.0429(6) Uani 1 1 d . . . . .
H3A H 0.785743 0.360731 -0.000787 0.051 Uiso 1 1 calc R U . . .
H3B H 0.801109 0.272310 -0.046189 0.051 Uiso 1 1 calc R U . . .
C4 C 0.89761(18) 0.37416(14) 0.25331(19) 0.0352(5) Uani 1 1 d . . . . .
C5 C 0.98229(19) 0.37159(14) 0.1681(2) 0.0370(5) Uani 1 1 d . . . . .
H5 H 0.998081 0.426692 0.144058 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5233(3) 0.33205(19) -0.0213(2) 0.0580(7) Uani 1 1 d . . . . .
H6 H 0.555831 0.316145 -0.087730 0.070 Uiso 1 1 calc R U . . .
C7 C 1.1718(2) 0.36639(15) 0.3245(2) 0.0425(5) Uani 1 1 d . . . . .
C8 C 0.9129(2) 0.43287(15) 0.3588(2) 0.0413(5) Uani 1 1 d . . . . .
H8A H 0.987325 0.427448 0.403994 0.050 Uiso 1 1 calc R U . . .
H8B H 0.861941 0.419279 0.413974 0.050 Uiso 1 1 calc R U . . .
C9 C 0.5105(2) 0.32471(18) 0.1927(2) 0.0513(6) Uani 1 1 d . . . . .
H9 H 0.534319 0.303270 0.270264 0.062 Uiso 1 1 calc R U . . .
C10 C 1.0907(2) 0.33063(15) 0.2262(2) 0.0429(5) Uani 1 1 d . . . . .
C11 C 0.9454(2) 0.31961(16) 0.0497(2) 0.0453(6) Uani 1 1 d . . . . .
C12 C 1.0997(2) 0.25868(17) 0.1750(3) 0.0578(7) Uani 1 1 d . . . . .
H12 H 1.159364 0.224378 0.198318 0.069 Uiso 1 1 calc R U . . .
C13 C 1.1900(2) 0.44909(16) 0.3345(2) 0.0466(6) Uani 1 1 d . . . . .
H13 H 1.148011 0.483539 0.278920 0.056 Uiso 1 1 calc R U . . .
C14 C 0.4277(2) 0.3818(2) 0.1754(3) 0.0565(7) Uani 1 1 d . . . . .
H14 H 0.396136 0.398673 0.241993 0.068 Uiso 1 1 calc R U . . .
C15 C 1.2691(2) 0.48118(19) 0.4251(2) 0.0554(7) Uani 1 1 d . . . . .
H15 H 1.279544 0.536719 0.428502 0.067 Uiso 1 1 calc R U . . .
C16 C 1.2370(2) 0.31785(19) 0.4107(3) 0.0571(7) Uani 1 1 d . . . . .
H16 H 1.227354 0.262245 0.407457 0.069 Uiso 1 1 calc R U . . .
C17 C 0.4394(3) 0.3888(2) -0.0359(3) 0.0705(9) Uani 1 1 d . . . . .
H17 H 0.415131 0.410220 -0.113396 0.085 Uiso 1 1 calc R U . . .
C18 C 0.9823(3) 0.3603(2) -0.0606(3) 0.0697(9) Uani 1 1 d . . . . .
H18A H 0.962994 0.326863 -0.131779 0.104 Uiso 1 1 calc R U . . .
H18B H 1.060895 0.368034 -0.044641 0.104 Uiso 1 1 calc R U . . .
H18C H 0.946334 0.411620 -0.074839 0.104 Uiso 1 1 calc R U . . .
C19 C 0.8941(3) 0.52003(17) 0.3180(3) 0.0584(7) Uani 1 1 d . . . . .
H19A H 0.948217 0.535273 0.268722 0.088 Uiso 1 1 calc R U . . .
H19B H 0.900639 0.554341 0.388700 0.088 Uiso 1 1 calc R U . . .
H19C H 0.821524 0.525472 0.270697 0.088 Uiso 1 1 calc R U . . .
C20 C 1.3329(2) 0.4333(2) 0.5104(3) 0.0591(8) Uani 1 1 d . . . . .
C21 C 0.3907(2) 0.41430(19) 0.0612(3) 0.0579(7) Uani 1 1 d . . . . .
C22 C 1.3160(2) 0.3511(2) 0.5010(3) 0.0659(9) Uani 1 1 d . . . . .
H22 H 1.358753 0.317089 0.556647 0.079 Uiso 1 1 calc R U . . .
C23 C 0.3007(3) 0.4775(3) 0.0443(4) 0.0875(12) Uani 1 1 d . . . . .
H23A H 0.230256 0.451821 0.041473 0.131 Uiso 1 1 calc R U . . .
H23B H 0.301925 0.505982 -0.031050 0.131 Uiso 1 1 calc R U . . .
H23C H 0.312826 0.514703 0.111589 0.131 Uiso 1 1 calc R U . . .
C24 C 1.4157(3) 0.4698(3) 0.6126(3) 0.0914(13) Uani 1 1 d . . . . .
H24A H 1.379681 0.482061 0.681135 0.137 Uiso 1 1 calc R U . . .
H24B H 1.445428 0.518398 0.583904 0.137 Uiso 1 1 calc R U . . .
H24C H 1.474419 0.432104 0.637510 0.137 Uiso 1 1 calc R U . . .
C25 C 1.0048(2) 0.23830(17) 0.0768(3) 0.0565(7) Uani 1 1 d . . . . .
H25A H 0.956537 0.198857 0.105413 0.068 Uiso 1 1 calc R U . . .
H25B H 1.030391 0.217425 0.004508 0.068 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 O2 1.4310(18) . ?
S1 O1 1.4310(18) . ?
S1 N1 1.635(2) . ?
S1 C2 1.757(3) . ?
N1 C1 1.425(3) . ?
N1 C3 1.468(3) . ?
C1 C4 1.326(3) . ?
C1 H1 0.9300 . ?
C2 C6 1.383(4) . ?
C2 C9 1.388(4) . ?
C3 C11 1.523(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.515(3) . ?
C4 C8 1.508(3) . ?
C5 C10 1.538(3) . ?
C5 C11 1.571(3) . ?
C5 H5 0.9800 . ?
C6 C17 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C13 1.391(4) . ?
C7 C16 1.395(4) . ?
C7 C10 1.472(4) . ?
C8 C19 1.521(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.333(4) . ?
C11 C18 1.527(3) . ?
C11 C25 1.539(4) . ?
C12 C25 1.495(4) . ?
C12 H12 0.9300 . ?
C13 C15 1.383(4) . ?
C13 H13 0.9300 . ?
C14 C21 1.379(4) . ?
C14 H14 0.9300 . ?
C15 C20 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C22 1.386(4) . ?
C16 H16 0.9300 . ?
C17 C21 1.379(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C22 1.382(5) . ?
C20 C24 1.516(4) . ?
C21 C23 1.512(4) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 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
O2 S1 O1 120.55(12) . . ?
O2 S1 N1 106.14(11) . . ?
O1 S1 N1 106.52(11) . . ?
O2 S1 C2 108.25(12) . . ?
O1 S1 C2 107.85(12) . . ?
N1 S1 C2 106.78(11) . . ?
C1 N1 C3 113.05(19) . . ?
C1 N1 S1 118.15(15) . . ?
C3 N1 S1 119.56(15) . . ?
C4 C1 N1 122.6(2) . . ?
C4 C1 H1 118.7 . . ?
N1 C1 H1 118.7 . . ?
C6 C2 C9 120.1(3) . . ?
C6 C2 S1 119.7(2) . . ?
C9 C2 S1 120.2(2) . . ?
N1 C3 C11 109.56(19) . . ?
N1 C3 H3A 109.8 . . ?
C11 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
C11 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C1 C4 C5 121.8(2) . . ?
C1 C4 C8 118.9(2) . . ?
C5 C4 C8 119.3(2) . . ?
C4 C5 C10 112.83(18) . . ?
C4 C5 C11 113.65(19) . . ?
C10 C5 C11 102.49(19) . . ?
C4 C5 H5 109.2 . . ?
C10 C5 H5 109.2 . . ?
C11 C5 H5 109.2 . . ?
C2 C6 C17 118.9(3) . . ?
C2 C6 H6 120.6 . . ?
C17 C6 H6 120.6 . . ?
C13 C7 C16 116.6(3) . . ?
C13 C7 C10 122.4(2) . . ?
C16 C7 C10 120.9(2) . . ?
C4 C8 C19 113.0(2) . . ?
C4 C8 H8A 109.0 . . ?
C19 C8 H8A 109.0 . . ?
C4 C8 H8B 109.0 . . ?
C19 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C2 119.6(3) . . ?
C14 C9 H9 120.2 . . ?
C2 C9 H9 120.2 . . ?
C12 C10 C7 125.5(2) . . ?
C12 C10 C5 110.2(2) . . ?
C7 C10 C5 124.3(2) . . ?
C3 C11 C18 108.1(2) . . ?
C3 C11 C25 111.6(2) . . ?
C18 C11 C25 110.5(2) . . ?
C3 C11 C5 111.83(19) . . ?
C18 C11 C5 109.9(2) . . ?
C25 C11 C5 104.9(2) . . ?
C10 C12 C25 113.7(3) . . ?
C10 C12 H12 123.2 . . ?
C25 C12 H12 123.2 . . ?
C15 C13 C7 121.4(3) . . ?
C15 C13 H13 119.3 . . ?
C7 C13 H13 119.3 . . ?
C21 C14 C9 121.3(3) . . ?
C21 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C13 C15 C20 121.9(3) . . ?
C13 C15 H15 119.1 . . ?
C20 C15 H15 119.1 . . ?
C22 C16 C7 121.2(3) . . ?
C22 C16 H16 119.4 . . ?
C7 C16 H16 119.4 . . ?
C21 C17 C6 121.8(3) . . ?
C21 C17 H17 119.1 . . ?
C6 C17 H17 119.1 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C15 117.2(3) . . ?
C22 C20 C24 121.6(3) . . ?
C15 C20 C24 121.1(3) . . ?
C14 C21 C17 118.3(3) . . ?
C14 C21 C23 120.5(3) . . ?
C17 C21 C23 121.2(3) . . ?
C20 C22 C16 121.7(3) . . ?
C20 C22 H22 119.2 . . ?
C16 C22 H22 119.2 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C12 C25 C11 103.3(2) . . ?
C12 C25 H25A 111.1 . . ?
C11 C25 H25A 111.1 . . ?
C12 C25 H25B 111.1 . . ?
C11 C25 H25B 111.1 . . ?
H25A C25 H25B 109.1 . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.044

