# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_190121C
_database_code_depnum_ccdc_archive 'CCDC 2036723'
loop_
_audit_author_name
_audit_author_address
'Hui Liu'
;shandong university of technology
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.7645(3)
_cell_length_b                   9.7049(3)
_cell_length_c                   13.5716(3)
_cell_angle_alpha                81.290(2)
_cell_angle_beta                 83.258(2)
_cell_angle_gamma                83.300(3)
_cell_volume                     998.78(5)
_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    0.125
_exptl_crystal_F_000             38
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.554
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.902
_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            5286
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.633
_diffrn_reflns_theta_max         47.990
_diffrn_reflns_theta_full        47.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1854
_reflns_number_gt                1744
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0699P)²+0.4865P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1854
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.617
_refine_ls_shift/su_mean         0.053

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 0.50875(10) 0.81201(8) 0.17589(6) 0.0482(4) Uani 1 1 d . . . . .
O1 O 0.4240(3) 0.9301(2) 0.11823(16) 0.0623(7) Uani 1 1 d . . . . .
O2 O 0.4126(3) 0.7386(2) 0.25969(16) 0.0626(7) Uani 1 1 d . . . . .
O3 O 0.7899(3) 0.5505(2) 0.45892(17) 0.0636(7) Uani 1 1 d . . . . .
O4 O 0.7834(6) 1.1519(4) 0.2151(3) 0.0691(13) Uani 0.5 1 d . . P . .
H4 H 0.7212 1.1216 0.2649 0.104 Uiso 0.5 1 d R U P . .
O4' O 0.9742(8) 1.1186(6) 0.1021(4) 0.0932(18) Uani 0.5 1 d . . P . .
H4' H 1.0702 1.0775 0.0878 0.140 Uiso 0.5 1 d R U P . .
N1 N 0.6745(3) 0.8673(2) 0.21918(17) 0.0469(7) Uani 1 1 d . . . . .
C1 C 0.6017(4) 0.6923(3) 0.0948(2) 0.0446(8) Uani 1 1 d . . . . .
C2 C 0.6360(4) 0.5528(3) 0.1316(3) 0.0549(9) Uani 1 1 d . . . . .
H2 H 0.6042 0.5207 0.1986 0.066 Uiso 1 1 calc R U . . .
C3 C 0.7179(5) 0.4606(4) 0.0682(3) 0.0643(10) Uani 1 1 d . . . . .
H3 H 0.7390 0.3662 0.0932 0.077 Uiso 1 1 calc R U . . .
C4 C 0.7686(4) 0.5056(4) -0.0306(3) 0.0610(10) Uani 1 1 d . . . . .
C5 C 0.7334(5) 0.6453(4) -0.0665(3) 0.0657(10) Uani 1 1 d . . . . .
H5 H 0.7679 0.6773 -0.1332 0.079 Uiso 1 1 calc R U . . .
C6 C 0.6481(4) 0.7389(4) -0.0057(2) 0.0582(9) Uani 1 1 d . . . . .
H6 H 0.6219 0.8323 -0.0317 0.070 Uiso 1 1 calc R U . . .
C7 C 0.8597(5) 0.4044(5) -0.0989(3) 0.0910(14) Uani 1 1 d . . . . .
H7A H 0.8439 0.4418 -0.1672 0.137 Uiso 1 1 calc R U . . .
H7B H 0.8111 0.3162 -0.0823 0.137 Uiso 1 1 calc R U . . .
H7C H 0.9818 0.3908 -0.0905 0.137 Uiso 1 1 calc R U . . .
C8 C 0.7655(4) 0.7630(3) 0.2916(2) 0.0526(9) Uani 1 1 d . . . . .
H8A H 0.8680 0.7180 0.2567 0.063 Uiso 1 1 calc R U . . .
H8B H 0.6891 0.6914 0.3194 0.063 Uiso 1 1 calc R U . . .
C9 C 0.8201(4) 0.8282(3) 0.3760(2) 0.0466(8) Uani 1 1 d . . . . .
C10 C 0.9360(4) 0.9222(3) 0.3574(3) 0.0572(9) Uani 1 1 d . . . . .
H10 H 0.9680 0.9573 0.4119 0.069 Uiso 1 1 calc R U . . .
C11 C 1.0191(5) 0.9762(4) 0.2557(3) 0.0694(11) Uani 1 1 d . . . . .
H11A H 1.0882 0.8987 0.2278 0.083 Uiso 1 1 calc R U . . .
H11B H 1.0981 1.0434 0.2632 0.083 Uiso 1 1 calc R U . . .
C12 C 0.8923(5) 1.0452(4) 0.1819(3) 0.0630(10) Uani 0.5 1 d . . P . .
H12 H 0.8893 1.0170 0.1197 0.076 Uiso 0.5 1 calc R U P . .
C12' C 0.8923(5) 1.0452(4) 0.1819(3) 0.0630(10) Uani 0.5 1 d . . P . .
H12' H 0.8968 1.0540 0.2488 0.076 Uiso 0.5 1 calc R U P . .
C13 C 0.7907(5) 0.9448(3) 0.1419(2) 0.0592(9) Uani 1 1 d . . . . .
H13A H 0.7212 0.9974 0.0912 0.071 Uiso 1 1 calc R U . . .
H13B H 0.8726 0.8779 0.1097 0.071 Uiso 1 1 calc R U . . .
C14 C 0.7400(4) 0.7877(3) 0.4798(2) 0.0477(8) Uani 1 1 d . . . . .
C15 C 0.7251(4) 0.6473(4) 0.5207(3) 0.0528(9) Uani 1 1 d . . . . .
C16 C 0.6540(5) 0.6134(4) 0.6188(3) 0.0681(10) Uani 1 1 d . . . . .
H16 H 0.6448 0.5202 0.6455 0.082 Uiso 1 1 calc R U . . .
C17 C 0.5972(5) 0.7173(5) 0.6766(3) 0.0773(11) Uani 1 1 d . . . . .
H17 H 0.5491 0.6938 0.7423 0.093 Uiso 1 1 calc R U . . .
C18 C 0.6103(5) 0.8548(5) 0.6392(3) 0.0739(11) Uani 1 1 d . . . . .
H18 H 0.5732 0.9246 0.6791 0.089 Uiso 1 1 calc R U . . .
C19 C 0.6796(4) 0.8888(4) 0.5409(3) 0.0590(9) Uani 1 1 d . . . . .
H19 H 0.6857 0.9827 0.5150 0.071 Uiso 1 1 calc R U . . .
C20 C 0.7789(5) 0.4050(3) 0.4942(3) 0.0762(12) Uani 1 1 d . . . . .
H20A H 0.6592 0.3883 0.5177 0.091 Uiso 1 1 calc R U . . .
H20B H 0.8501 0.3745 0.5491 0.091 Uiso 1 1 calc R U . . .
C21 C 0.8431(6) 0.3269(4) 0.4082(4) 0.0889(13) Uani 1 1 d . . . . .
H21A H 0.7712 0.3576 0.3545 0.133 Uiso 1 1 calc R U . . .
H21B H 0.8381 0.2284 0.4292 0.133 Uiso 1 1 calc R U . . .
H21C H 0.9613 0.3447 0.3854 0.133 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 1.426(2) . ?
S1 O2 1.428(2) . ?
S1 N1 1.650(3) . ?
S1 C1 1.757(3) . ?
O3 C15 1.367(4) . ?
O3 C20 1.430(4) . ?
O4 C12 1.356(5) . ?
O4 H4 0.8200 . ?
O4' H4' 0.8200 . ?
N1 C13 1.475(4) . ?
N1 C8 1.478(4) . ?
C1 C2 1.376(4) . ?
C1 C6 1.390(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 C7 1.511(5) . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.513(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.333(4) . ?
C9 C14 1.486(4) . ?
C10 C11 1.499(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.515(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.385(4) . ?
C14 C15 1.403(5) . ?
C15 C16 1.387(5) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.493(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 119.34(13) . . ?
O1 S1 N1 106.96(13) . . ?
O2 S1 N1 106.77(13) . . ?
O1 S1 C1 108.51(14) . . ?
O2 S1 C1 108.84(14) . . ?
N1 S1 C1 105.59(13) . . ?
C15 O3 C20 119.3(3) . . ?
C12 O4 H4 109.5 . . ?
C13 N1 C8 114.7(3) . . ?
C13 N1 S1 114.3(2) . . ?
C8 N1 S1 114.77(18) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 S1 120.1(2) . . ?
C6 C1 S1 120.2(2) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 C7 121.0(4) . . ?
C5 C4 C7 120.6(4) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 112.3(2) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C14 120.5(3) . . ?
C10 C9 C8 120.5(3) . . ?
C14 C9 C8 119.0(3) . . ?
C9 C10 C11 125.4(3) . . ?
C9 C10 H10 117.3 . . ?
C11 C10 H10 117.3 . . ?
C10 C11 C12 114.8(3) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
O4 C12 C11 113.7(3) . . ?
O4 C12 H12 123.1 . . ?
C11 C12 H12 123.2 . . ?
N1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C19 C14 C15 117.3(3) . . ?
C19 C14 C9 120.5(3) . . ?
C15 C14 C9 122.2(3) . . ?
O3 C15 C16 124.0(3) . . ?
O3 C15 C14 115.5(3) . . ?
C16 C15 C14 120.4(3) . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.1(4) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 122.2(3) . . ?
C18 C19 H19 118.9 . . ?
C14 C19 H19 118.9 . . ?
O3 C20 C21 107.1(3) . . ?
O3 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O3 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.054

