# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_ay210629-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2142411'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2022-08-17 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         'C10 H13 N O3 S'
_chemical_formula_sum            'C10 H13 N O3 S'
_chemical_formula_weight         227.27

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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.70520(10)
_cell_length_b                   7.70520(10)
_cell_length_c                   36.3563(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2158.48(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    3922
_cell_measurement_theta_min      4.8560
_cell_measurement_theta_max      74.7830

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.581
_shelx_estimated_absorpt_T_min   0.683
_shelx_estimated_absorpt_T_max   0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  0.783
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6574
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         4.866
_diffrn_reflns_theta_max         75.916
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2182
_reflns_number_gt                2006
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.557
_reflns_Friedel_fraction_max     0.931
_reflns_Friedel_fraction_full    0.992

_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       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_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)+(0.0551P)²+0.2337P] 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 693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(15)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2182
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 1.05680(9) 0.49914(9) 0.47891(2) 0.0538(2) Uani 1 1 d . . . . .
O2 O 1.0905(4) 0.3377(4) 0.46147(6) 0.0865(7) Uani 1 1 d . . . . .
O1 O 1.0633(4) 0.6524(3) 0.45733(6) 0.0840(7) Uani 1 1 d . . . . .
O3 O 0.5851(3) 0.5064(4) 0.56012(8) 0.0984(10) Uani 1 1 d . . . . .
N1 N 0.8548(3) 0.4885(3) 0.49784(6) 0.0591(6) Uani 1 1 d . . . . .
C2 C 1.0414(3) 0.5783(3) 0.54845(6) 0.0396(4) Uani 1 1 d . . . . .
C6 C 1.0215(3) 0.4890(3) 0.58656(6) 0.0438(5) Uani 1 1 d . . . . .
C1 C 1.1777(3) 0.5220(3) 0.52089(6) 0.0463(5) Uani 1 1 d . . . . .
H1A H 1.2302 0.4127 0.5281 0.056 Uiso 1 1 calc R U . . .
H1B H 1.2679 0.6091 0.5184 0.056 Uiso 1 1 calc R U . . .
C3 C 0.8695(3) 0.5321(3) 0.53146(7) 0.0461(5) Uani 1 1 d . . . . .
C10 C 0.9974(4) 0.2924(3) 0.58437(8) 0.0563(6) Uani 1 1 d . . . . .
H10A H 0.9039 0.2660 0.5678 0.084 Uiso 1 1 calc R U . . .
H10B H 0.9708 0.2478 0.6084 0.084 Uiso 1 1 calc R U . . .
H10C H 1.1024 0.2398 0.5755 0.084 Uiso 1 1 calc R U . . .
C5 C 0.8487(4) 0.5850(4) 0.59530(8) 0.0586(7) Uani 1 1 d . . . . .
H5 H 0.7978 0.5576 0.6193 0.070 Uiso 1 1 calc R U . . .
C9 C 1.1702(4) 0.5300(4) 0.61294(7) 0.0634(7) Uani 1 1 d . . . . .
H9A H 1.2768 0.4852 0.6031 0.095 Uiso 1 1 calc R U . . .
H9B H 1.1476 0.4772 0.6364 0.095 Uiso 1 1 calc R U . . .
H9C H 1.1798 0.6534 0.6159 0.095 Uiso 1 1 calc R U . . .
C4 C 0.7379(3) 0.5371(4) 0.56262(9) 0.0624(7) Uani 1 1 d . . . . .
C8 C 0.8966(5) 0.7776(4) 0.58967(9) 0.0715(9) Uani 1 1 d . . . . .
H8A H 0.9487 0.8258 0.6117 0.086 Uiso 1 1 calc R U . . .
H8B H 0.7951 0.8455 0.5832 0.086 Uiso 1 1 calc R U . . .
C7 C 1.0283(4) 0.7736(3) 0.55760(8) 0.0607(7) Uani 1 1 d . . . . .
H7A H 0.9860 0.8392 0.5367 0.073 Uiso 1 1 calc R U . . .
H7B H 1.1398 0.8199 0.5651 0.073 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 1.419(2) . ?
S1 O2 1.420(2) . ?
S1 N1 1.704(2) . ?
S1 C1 1.797(2) . ?
O3 C4 1.204(4) . ?
N1 C3 1.273(3) . ?
C2 C3 1.504(3) . ?
C2 C1 1.515(3) . ?
C2 C7 1.544(3) . ?
C2 C6 1.555(3) . ?
C6 C9 1.528(3) . ?
C6 C10 1.528(4) . ?
C6 C5 1.556(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C4 1.521(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 C4 1.509(5) . ?
C5 C8 1.542(5) . ?
C5 H5 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 C7 1.546(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 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 118.40(16) . . ?
O1 S1 N1 107.20(15) . . ?
O2 S1 N1 107.78(16) . . ?
O1 S1 C1 111.71(14) . . ?
O2 S1 C1 111.74(14) . . ?
N1 S1 C1 97.78(10) . . ?
C3 N1 S1 107.08(17) . . ?
C3 C2 C1 105.72(18) . . ?
C3 C2 C7 105.1(2) . . ?
C1 C2 C7 117.8(2) . . ?
C3 C2 C6 100.04(17) . . ?
C1 C2 C6 122.08(19) . . ?
C7 C2 C6 103.5(2) . . ?
C9 C6 C10 109.2(2) . . ?
C9 C6 C2 113.20(19) . . ?
C10 C6 C2 113.8(2) . . ?
C9 C6 C5 114.5(2) . . ?
C10 C6 C5 112.2(2) . . ?
C2 C6 C5 93.21(18) . . ?
C2 C1 S1 103.32(15) . . ?
C2 C1 H1A 111.1 . . ?
S1 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
S1 C1 H1B 111.1 . . ?
H1A C1 H1B 109.1 . . ?
N1 C3 C2 122.4(2) . . ?
N1 C3 C4 131.5(2) . . ?
C2 C3 C4 106.0(2) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C8 105.5(2) . . ?
C4 C5 C6 101.9(2) . . ?
C8 C5 C6 103.0(2) . . ?
C4 C5 H5 114.9 . . ?
C8 C5 H5 114.9 . . ?
C6 C5 H5 114.9 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C4 C5 131.3(3) . . ?
O3 C4 C3 126.2(3) . . ?
C5 C4 C3 102.4(2) . . ?
C5 C8 C7 103.8(2) . . ?
C5 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
C5 C8 H8B 111.0 . . ?
C7 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C2 C7 C8 103.0(2) . . ?
C2 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C2 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C3 -104.0(2) . . . . ?
O2 S1 N1 C3 127.5(2) . . . . ?
C1 S1 N1 C3 11.6(2) . . . . ?
C3 C2 C6 C9 -173.3(2) . . . . ?
C1 C2 C6 C9 70.9(3) . . . . ?
C7 C2 C6 C9 -64.9(3) . . . . ?
C3 C2 C6 C10 61.2(2) . . . . ?
C1 C2 C6 C10 -54.6(3) . . . . ?
C7 C2 C6 C10 169.6(2) . . . . ?
C3 C2 C6 C5 -54.8(2) . . . . ?
C1 C2 C6 C5 -170.6(2) . . . . ?
C7 C2 C6 C5 53.6(2) . . . . ?
C3 C2 C1 S1 18.0(2) . . . . ?
C7 C2 C1 S1 -99.1(2) . . . . ?
C6 C2 C1 S1 130.92(19) . . . . ?
O1 S1 C1 C2 94.23(19) . . . . ?
O2 S1 C1 C2 -130.55(19) . . . . ?
N1 S1 C1 C2 -17.83(18) . . . . ?
S1 N1 C3 C2 -1.1(3) . . . . ?
S1 N1 C3 C4 -175.9(2) . . . . ?
C1 C2 C3 N1 -12.4(3) . . . . ?
C7 C2 C3 N1 113.0(3) . . . . ?
C6 C2 C3 N1 -140.0(3) . . . . ?
C1 C2 C3 C4 163.5(2) . . . . ?
C7 C2 C3 C4 -71.1(2) . . . . ?
C6 C2 C3 C4 35.9(2) . . . . ?
C9 C6 C5 C4 173.2(2) . . . . ?
C10 C6 C5 C4 -61.6(3) . . . . ?
C2 C6 C5 C4 55.8(2) . . . . ?
C9 C6 C5 C8 64.0(3) . . . . ?
C10 C6 C5 C8 -170.8(2) . . . . ?
C2 C6 C5 C8 -53.4(2) . . . . ?
C8 C5 C4 O3 -109.1(4) . . . . ?
C6 C5 C4 O3 143.6(4) . . . . ?
C8 C5 C4 C3 71.9(3) . . . . ?
C6 C5 C4 C3 -35.4(3) . . . . ?
N1 C3 C4 O3 -4.1(5) . . . . ?
C2 C3 C4 O3 -179.5(3) . . . . ?
N1 C3 C4 C5 174.9(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C4 C5 C8 C7 -71.9(3) . . . . ?
C6 C5 C8 C7 34.6(3) . . . . ?
C3 C2 C7 C8 70.0(3) . . . . ?
C1 C2 C7 C8 -172.6(2) . . . . ?
C6 C2 C7 C8 -34.5(3) . . . . ?
C5 C8 C7 C2 -0.1(3) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_ay210529-3-rt_auto
_database_code_depnum_ccdc_archive 'CCDC 2142412'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_audit_creation_date             2022-08-08
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N O3 S'
_chemical_formula_sum            'C10 H13 N O3 S'
_chemical_formula_weight         227.27
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.70250(10)
_cell_length_b                   7.70250(10)
_cell_length_c                   36.3548(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2156.88(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3775
_cell_measurement_temperature    301.63(10)
_cell_measurement_theta_max      75.0240
_cell_measurement_theta_min      5.8600
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.698
_exptl_absorpt_coefficient_mu    2.582
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            5750
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.845
_diffrn_reflns_theta_min         4.866
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.63(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  60.00   0.50    1.59    --  107.00 -61.00 -60.00   50
  2  ω     43.00 113.00   0.50    1.59    --  107.00-128.00  46.00  140
  3  ω     48.00  73.00   0.50    1.59    --  107.00 -94.00  60.00   50
  4  ω     55.00 112.00   0.50    1.59    --  107.00-125.00 120.00  114
  5  ω    -65.00  25.00   0.50    0.40    --  -45.28  61.00-113.00  180
  6  ω   -136.00 -95.00   0.50    1.59    -- -102.00 -59.00 -78.00   82
  7  ω   -173.00-142.00   0.50    1.59    -- -102.00 -59.00 -78.00   62
  8  ω    -56.00 -30.00   0.50    1.59    -- -102.00  59.00  61.00   52
  9  ω    -24.00  12.00   0.50    0.40    --  -45.28  19.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1431831000
_diffrn_orient_matrix_UB_12      -0.1382568000
_diffrn_orient_matrix_UB_13      -0.0041319000
_diffrn_orient_matrix_UB_21      -0.0072909000
_diffrn_orient_matrix_UB_22      0.0205552000
_diffrn_orient_matrix_UB_23      -0.0421234000
_diffrn_orient_matrix_UB_31      0.1394776000
_diffrn_orient_matrix_UB_32      0.1430374000
_diffrn_orient_matrix_UB_33      0.0020729000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.542
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                1962
_reflns_number_total             2123
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(11)
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0675P)²+0.1995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C3
 1.48 with sigma of 0.002
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C4(H4A,H4B)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.05695(10) 0.49947(10) 0.22899(2) 0.0565(2) Uani 1 1 d . . . . .
O1 O -0.0908(4) 0.3383(4) 0.21161(7) 0.0904(8) Uani 1 1 d . . . . .
O2 O -0.0634(4) 0.6527(4) 0.20737(6) 0.0864(8) Uani 1 1 d . . . . .
O3 O 0.4143(3) 0.5075(5) 0.31030(8) 0.0977(10) Uani 1 1 d . . . . .
N1 N 0.1447(3) 0.4896(4) 0.24783(6) 0.0619(6) Uani 1 1 d . . . . .
C2 C -0.0417(3) 0.5788(3) 0.29846(6) 0.0421(5) Uani 1 1 d . . . . .
C8 C -0.0217(3) 0.4888(3) 0.33653(6) 0.0466(5) Uani 1 1 d . . . . .
C1 C -0.1782(3) 0.5224(4) 0.27088(6) 0.0485(6) Uani 1 1 d . . . . .
H1A H -0.268328 0.609556 0.268358 0.058 Uiso 1 1 calc R U . . .
H1B H -0.230833 0.413134 0.278059 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1310(3) 0.5327(4) 0.28172(6) 0.0489(6) Uani 1 1 d D . . . .
C10 C 0.0019(4) 0.2926(4) 0.33427(8) 0.0591(7) Uani 1 1 d . . . . .
H10A H -0.102945 0.240456 0.325232 0.089 Uiso 1 1 calc R U . . .
H10B H 0.027552 0.247624 0.358288 0.089 Uiso 1 1 calc R U . . .
H10C H 0.095928 0.266221 0.317864 0.089 Uiso 1 1 calc R U . . .
C6 C 0.1507(4) 0.5853(4) 0.34533(8) 0.0615(7) Uani 1 1 d . . . . .
H6 H 0.202081 0.557555 0.369273 0.074 Uiso 1 1 calc R U . . .
C9 C -0.1698(4) 0.5306(5) 0.36303(7) 0.0661(8) Uani 1 1 d . . . . .
H9A H -0.175241 0.653805 0.366890 0.099 Uiso 1 1 calc R U . . .
H9B H -0.149632 0.473379 0.386092 0.099 Uiso 1 1 calc R U . . .
H9C H -0.277515 0.490980 0.352754 0.099 Uiso 1 1 calc R U . . .
C7 C 0.2606(3) 0.5367(5) 0.31233(8) 0.0650(8) Uani 1 1 d D . . . .
C5 C 0.1040(5) 0.7770(5) 0.33971(9) 0.0752(10) Uani 1 1 d . . . . .
H5A H 0.205807 0.844304 0.333089 0.090 Uiso 1 1 calc R U . . .
H5B H 0.053063 0.825903 0.361804 0.090 Uiso 1 1 calc R U . . .
C4 C -0.0295(5) 0.7738(4) 0.30773(8) 0.0638(8) Uani 1 1 d . . . . .
H4A H -0.140996 0.819359 0.315526 0.077 Uiso 1 1 calc R U . . .
H4B H 0.011697 0.840228 0.286810 0.077 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 1.417(3) . ?
S1 O2 1.419(2) . ?
S1 N1 1.699(3) . ?
S1 C1 1.795(2) . ?
O3 C7 1.208(4) . ?
N1 C3 1.280(3) . ?
C2 C8 1.556(3) . ?
C2 C1 1.516(3) . ?
C2 C3 1.505(3) . ?
C2 C4 1.542(4) . ?
C8 C10 1.524(4) . ?
C8 C6 1.554(4) . ?
C8 C9 1.527(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C7 1.495(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C6 H6 0.9800 . ?
C6 C7 1.516(5) . ?
C6 C5 1.533(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.552(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 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 118.37(17) . . ?
O1 S1 N1 107.99(17) . . ?
O1 S1 C1 111.63(15) . . ?
O2 S1 N1 107.02(16) . . ?
O2 S1 C1 111.70(15) . . ?
N1 S1 C1 97.93(11) . . ?
C3 N1 S1 107.52(18) . . ?
C1 C2 C8 122.0(2) . . ?
C1 C2 C4 117.8(2) . . ?
C3 C2 C8 99.61(18) . . ?
C3 C2 C1 106.14(19) . . ?
C3 C2 C4 105.3(2) . . ?
C4 C2 C8 103.5(2) . . ?
C10 C8 C2 113.9(2) . . ?
C10 C8 C6 112.6(2) . . ?
C10 C8 C9 109.4(2) . . ?
C6 C8 C2 93.14(19) . . ?
C9 C8 C2 113.1(2) . . ?
C9 C8 C6 114.0(2) . . ?
S1 C1 H1A 111.1 . . ?
S1 C1 H1B 111.1 . . ?
C2 C1 S1 103.20(16) . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.1 . . ?
N1 C3 C2 121.5(2) . . ?
N1 C3 C7 131.8(3) . . ?
C7 C3 C2 106.5(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C6 H6 115.0 . . ?
C7 C6 C8 101.3(2) . . ?
C7 C6 H6 115.0 . . ?
C7 C6 C5 105.3(3) . . ?
C5 C6 C8 103.5(3) . . ?
C5 C6 H6 115.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C7 C3 127.3(3) . . ?
O3 C7 C6 129.9(3) . . ?
C3 C7 C6 102.8(2) . . ?
C6 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
C6 C5 C4 103.9(2) . . ?
H5A C5 H5B 109.0 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
C2 C4 C5 102.7(2) . . ?
C2 C4 H4A 111.2 . . ?
C2 C4 H4B 111.2 . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.923
_oxdiff_exptl_absorpt_empirical_full_min 0.576
####################################################################### 
# 
# 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_ay210630-1-300k_auto
_database_code_depnum_ccdc_archive 'CCDC 2142409'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2022-08-17 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         'C13 H19 N O4 S'
_chemical_formula_sum            'C13 H19 N O4 S'
_chemical_formula_weight         285.35

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                   7.7460(2)
_cell_length_b                   7.02320(10)
_cell_length_c                   12.3152(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.185(2)
_cell_angle_gamma                90
_cell_volume                     663.14(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    6082
_cell_measurement_theta_min      3.5880
_cell_measurement_theta_max      75.0660

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.274
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6728
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.626
_diffrn_reflns_theta_max         75.386
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2548
_reflns_number_gt                2491
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.866
_reflns_Friedel_fraction_full    0.938

_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       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL 2018/1 (Sheldrick, 2015)'
_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)+(0.0964P)²] 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 1038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(16)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2548
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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 0.78305(8) 0.38968(11) 0.44108(5) 0.0401(2) Uani 1 1 d . . . . .
O3 O 0.6524(3) 0.2433(3) 0.18489(18) 0.0440(5) Uani 1 1 d . . . . .
O1 O 0.7625(3) 0.2011(4) 0.4820(2) 0.0571(7) Uani 1 1 d . . . . .
N1 N 0.6262(3) 0.4416(4) 0.3385(2) 0.0398(6) Uani 1 1 d . . . . .
O2 O 0.7938(4) 0.5378(5) 0.5211(2) 0.0597(7) Uani 1 1 d . . . . .
O4 O 0.4600(4) 0.6161(5) 0.1177(3) 0.0688(8) Uani 1 1 d . . . . .
C2 C 0.8822(4) 0.4722(4) 0.2490(2) 0.0358(6) Uani 1 1 d . . . . .
C1 C 0.9599(3) 0.4016(5) 0.3622(2) 0.0393(6) Uani 1 1 d . . . . .
H1A H 1.048882 0.488867 0.395806 0.047 Uiso 1 1 calc R U . . .
H1B H 1.012031 0.276970 0.357148 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6843(4) 0.4259(4) 0.2328(2) 0.0359(6) Uani 1 1 d . . . . .
C10 C 0.9559(4) 0.3914(6) 0.1494(2) 0.0460(6) Uani 1 1 d . . . . .
H10A H 0.925210 0.258288 0.137844 0.055 Uiso 1 1 calc R U . . .
H10B H 1.081813 0.404406 0.157852 0.055 Uiso 1 1 calc R U . . .
C9 C 0.8863(4) 0.6925(4) 0.2266(3) 0.0440(7) Uani 1 1 d . . . . .
C6 C 0.4486(4) 0.3709(6) 0.3473(3) 0.0504(7) Uani 1 1 d . . . . .
H6A H 0.362911 0.460509 0.312339 0.060 Uiso 1 1 calc R U . . .
H6B H 0.433968 0.361249 0.424052 0.060 Uiso 1 1 calc R U . . .
C7 C 0.6116(4) 0.5808(5) 0.1478(3) 0.0464(7) Uani 1 1 d . . . . .
C5 C 0.4192(5) 0.1786(6) 0.2934(3) 0.0559(8) Uani 1 1 d . . . . .
H5A H 0.296674 0.145267 0.287718 0.067 Uiso 1 1 calc R U . . .
H5B H 0.485747 0.083091 0.338405 0.067 Uiso 1 1 calc R U . . .
C8 C 0.7703(5) 0.6728(5) 0.1133(3) 0.0502(7) Uani 1 1 d . . . . .
H8 H 0.748069 0.792117 0.072528 0.060 Uiso 1 1 calc R U . . .
C13 C 0.8043(5) 0.8206(5) 0.3054(3) 0.0556(8) Uani 1 1 d . . . . .
H13A H 0.685592 0.782593 0.306791 0.083 Uiso 1 1 calc R U . . .
H13B H 0.807063 0.950421 0.281273 0.083 Uiso 1 1 calc R U . . .
H13C H 0.868685 0.809474 0.377738 0.083 Uiso 1 1 calc R U . . .
C4 C 0.4738(5) 0.1796(6) 0.1803(3) 0.0560(8) Uani 1 1 d . . . . .
H4A H 0.462515 0.052321 0.149524 0.067 Uiso 1 1 calc R U . . .
H4B H 0.397524 0.263420 0.132652 0.067 Uiso 1 1 calc R U . . .
C12 C 1.0692(5) 0.7699(6) 0.2195(3) 0.0578(9) Uani 1 1 d . . . . .
H12A H 1.138154 0.764851 0.290636 0.087 Uiso 1 1 calc R U . . .
H12B H 1.060652 0.899425 0.194330 0.087 Uiso 1 1 calc R U . . .
H12C H 1.123354 0.694039 0.168942 0.087 Uiso 1 1 calc R U . . .
C11 C 0.8660(5) 0.5172(6) 0.0543(3) 0.0553(8) Uani 1 1 d . . . . .
H11A H 0.783868 0.443367 0.004303 0.066 Uiso 1 1 calc R U . . .
H11B H 0.951386 0.573831 0.013571 0.066 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 1.427(3) . ?
S1 O1 1.434(3) . ?
S1 N1 1.664(3) . ?
S1 C1 1.791(3) . ?
O3 C3 1.418(3) . ?
O3 C4 1.447(4) . ?
N1 C3 1.441(4) . ?
N1 C6 1.481(4) . ?
O4 C7 1.206(5) . ?
C2 C1 1.521(4) . ?
C2 C10 1.534(4) . ?
C2 C3 1.552(4) . ?
C2 C9 1.572(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C7 1.558(4) . ?
C10 C11 1.552(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 C13 1.527(5) . ?
C9 C12 1.532(5) . ?
C9 C8 1.554(5) . ?
C6 C5 1.508(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.503(5) . ?
C5 C4 1.514(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 C11 1.558(5) . ?
C8 H8 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 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 115.41(19) . . ?
O2 S1 N1 109.22(15) . . ?
O1 S1 N1 111.33(15) . . ?
O2 S1 C1 111.51(16) . . ?
O1 S1 C1 111.44(16) . . ?
N1 S1 C1 96.29(13) . . ?
C3 O3 C4 113.9(2) . . ?
C3 N1 C6 117.0(2) . . ?
C3 N1 S1 112.43(19) . . ?
C6 N1 S1 117.1(2) . . ?
C1 C2 C10 117.9(2) . . ?
C1 C2 C3 107.7(2) . . ?
C10 C2 C3 107.0(2) . . ?
C1 C2 C9 117.8(3) . . ?
C10 C2 C9 101.8(3) . . ?
C3 C2 C9 103.2(2) . . ?
C2 C1 S1 106.21(18) . . ?
C2 C1 H1A 110.5 . . ?
S1 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
S1 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
O3 C3 N1 112.7(2) . . ?
O3 C3 C2 110.7(2) . . ?
N1 C3 C2 107.3(2) . . ?
O3 C3 C7 109.1(2) . . ?
N1 C3 C7 115.1(2) . . ?
C2 C3 C7 101.3(2) . . ?
C2 C10 C11 102.4(3) . . ?
C2 C10 H10A 111.3 . . ?
C11 C10 H10A 111.3 . . ?
C2 C10 H10B 111.3 . . ?
C11 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
C13 C9 C12 107.4(3) . . ?
C13 C9 C8 112.5(3) . . ?
C12 C9 C8 113.6(3) . . ?
C13 C9 C2 116.6(3) . . ?
C12 C9 C2 113.7(3) . . ?
C8 C9 C2 92.6(2) . . ?
N1 C6 C5 110.6(3) . . ?
N1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O4 C7 C8 128.7(3) . . ?
O4 C7 C3 126.4(3) . . ?
C8 C7 C3 104.9(3) . . ?
C6 C5 C4 110.9(3) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C8 C9 100.2(2) . . ?
C7 C8 C11 107.1(3) . . ?
C9 C8 C11 103.2(3) . . ?
C7 C8 H8 114.9 . . ?
C9 C8 H8 114.9 . . ?
C11 C8 H8 114.9 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C4 C5 110.9(3) . . ?
O3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 C8 103.8(2) . . ?
C10 C11 H11A 111.0 . . ?
C8 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
C8 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?

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
O2 S1 N1 C3 129.8(2) . . . . ?
O1 S1 N1 C3 -101.5(2) . . . . ?
C1 S1 N1 C3 14.4(2) . . . . ?
O2 S1 N1 C6 -90.5(3) . . . . ?
O1 S1 N1 C6 38.2(3) . . . . ?
C1 S1 N1 C6 154.1(3) . . . . ?
C10 C2 C1 S1 -144.0(3) . . . . ?
C3 C2 C1 S1 -22.9(3) . . . . ?
C9 C2 C1 S1 93.2(3) . . . . ?
O2 S1 C1 C2 -107.6(2) . . . . ?
O1 S1 C1 C2 121.9(2) . . . . ?
N1 S1 C1 C2 6.0(2) . . . . ?
C4 O3 C3 N1 52.2(3) . . . . ?
C4 O3 C3 C2 172.4(3) . . . . ?
C4 O3 C3 C7 -76.9(3) . . . . ?
C6 N1 C3 O3 -47.4(3) . . . . ?
S1 N1 C3 O3 92.4(2) . . . . ?
C6 N1 C3 C2 -169.5(3) . . . . ?
S1 N1 C3 C2 -29.8(3) . . . . ?
C6 N1 C3 C7 78.6(3) . . . . ?
S1 N1 C3 C7 -141.6(2) . . . . ?
C1 C2 C3 O3 -90.1(3) . . . . ?
C10 C2 C3 O3 37.7(3) . . . . ?
C9 C2 C3 O3 144.6(2) . . . . ?
C1 C2 C3 N1 33.3(3) . . . . ?
C10 C2 C3 N1 161.0(2) . . . . ?
C9 C2 C3 N1 -92.0(2) . . . . ?
C1 C2 C3 C7 154.3(2) . . . . ?
C10 C2 C3 C7 -78.0(3) . . . . ?
C9 C2 C3 C7 29.0(3) . . . . ?
C1 C2 C10 C11 -171.8(3) . . . . ?
C3 C2 C10 C11 66.7(3) . . . . ?
C9 C2 C10 C11 -41.3(3) . . . . ?
C1 C2 C9 C13 -55.1(4) . . . . ?
C10 C2 C9 C13 174.3(3) . . . . ?
C3 C2 C9 C13 63.4(3) . . . . ?
C1 C2 C9 C12 70.7(3) . . . . ?
C10 C2 C9 C12 -59.9(3) . . . . ?
C3 C2 C9 C12 -170.8(3) . . . . ?
C1 C2 C9 C8 -172.0(2) . . . . ?
C10 C2 C9 C8 57.4(3) . . . . ?
C3 C2 C9 C8 -53.5(2) . . . . ?
C3 N1 C6 C5 46.1(4) . . . . ?
S1 N1 C6 C5 -91.8(3) . . . . ?
O3 C3 C7 O4 71.6(4) . . . . ?
N1 C3 C7 O4 -56.2(5) . . . . ?
C2 C3 C7 O4 -171.6(4) . . . . ?
O3 C3 C7 C8 -108.4(3) . . . . ?
N1 C3 C7 C8 123.8(3) . . . . ?
C2 C3 C7 C8 8.4(3) . . . . ?
N1 C6 C5 C4 -48.5(4) . . . . ?
O4 C7 C8 C9 136.8(4) . . . . ?
C3 C7 C8 C9 -43.2(3) . . . . ?
O4 C7 C8 C11 -115.8(4) . . . . ?
C3 C7 C8 C11 64.2(3) . . . . ?
C13 C9 C8 C7 -62.1(3) . . . . ?
C12 C9 C8 C7 175.5(3) . . . . ?
C2 C9 C8 C7 58.2(3) . . . . ?
C13 C9 C8 C11 -172.5(3) . . . . ?
C12 C9 C8 C11 65.1(4) . . . . ?
C2 C9 C8 C11 -52.2(3) . . . . ?
C3 O3 C4 C5 -56.8(4) . . . . ?
C6 C5 C4 O3 54.6(4) . . . . ?
C2 C10 C11 C8 7.2(4) . . . . ?
C7 C8 C11 C10 -75.6(3) . . . . ?
C9 C8 C11 C10 29.6(4) . . . . ?

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_aysyn210531-2-293k_re
_database_code_depnum_ccdc_archive 'CCDC 2142410'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_audit_creation_date             2022-08-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H19 N O4 S'
_chemical_formula_sum            'C13 H19 N O4 S'
_chemical_formula_weight         285.35
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7428(3)
_cell_length_b                   7.0274(2)
_cell_length_c                   12.3154(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.214(3)
_cell_angle_gamma                90
_cell_volume                     663.23(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5770
_cell_measurement_temperature    292.6(2)
_cell_measurement_theta_max      30.7480
_cell_measurement_theta_min      1.8080
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6583
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.861
_diffrn_reflns_theta_min         2.658
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.6(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  51.00   0.50    1.20    --    5.05  37.00-120.00   82
  2  ω    -38.00  20.00   0.50    1.20    --    5.05 -57.00  29.00  116
  3  ω     -7.00  26.00   0.50    1.20    --    5.05  57.00 171.00   66
  4  ω     32.00  78.00   0.50    1.20    --    5.05  57.00 171.00   92
  5  ω    -18.00   7.00   0.50    1.20    --   -5.21 -99.00   0.00   50
  6  ω    -17.00  16.00   0.50    1.20    --   -5.21 -99.00  30.00   66
  7  ω    -18.00  28.00   0.50    1.20    --   -5.21 -99.00-150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088947000
_diffrn_orient_matrix_UB_12      -0.0130809000
_diffrn_orient_matrix_UB_13      0.0576528000
_diffrn_orient_matrix_UB_21      -0.0672057000
_diffrn_orient_matrix_UB_22      0.0674686000
_diffrn_orient_matrix_UB_23      0.0030906000
_diffrn_orient_matrix_UB_31      -0.0629483000
_diffrn_orient_matrix_UB_32      -0.0739619000
_diffrn_orient_matrix_UB_33      -0.0073662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.625
_reflns_number_gt                2895
_reflns_number_total             3016
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3016
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.0364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0740
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C3(H3A,H3B), C1(H1A,H1B), C2(H2A,H2B), C11(H11A,
 H11B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.78306(5) 0.61036(6) 0.44106(3) 0.03211(12) Uani 1 1 d . . . . .
O3 O 0.65232(18) 0.75671(19) 0.18487(11) 0.0352(3) Uani 1 1 d . . . . .
O1 O 0.7624(2) 0.7996(2) 0.48192(13) 0.0493(4) Uani 1 1 d . . . . .
O2 O 0.7940(2) 0.4612(3) 0.52114(13) 0.0518(4) Uani 1 1 d . . . . .
O4 O 0.4594(2) 0.3839(3) 0.11749(15) 0.0600(5) Uani 1 1 d . . . . .
N1 N 0.62634(19) 0.5579(2) 0.33871(12) 0.0313(3) Uani 1 1 d . . . . .
C4 C 0.6843(2) 0.5740(2) 0.23254(13) 0.0282(3) Uani 1 1 d . . . . .
C9 C 0.9595(2) 0.5987(3) 0.36249(13) 0.0310(3) Uani 1 1 d . . . . .
H9A H 1.011451 0.723463 0.357494 0.037 Uiso 1 1 calc R U . . .
H9B H 1.048676 0.511819 0.396249 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8824(2) 0.5281(2) 0.24937(13) 0.0275(3) Uani 1 1 d . . . . .
C10 C 0.9562(2) 0.6088(4) 0.14959(14) 0.0379(4) Uani 1 1 d . . . . .
H10A H 1.082131 0.595921 0.158035 0.045 Uiso 1 1 calc R U . . .
H10B H 0.925320 0.741760 0.137875 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7702(3) 0.3272(3) 0.11283(16) 0.0413(4) Uani 1 1 d . . . . .
H6 H 0.748121 0.207949 0.071956 0.050 Uiso 1 1 calc R U . . .
C7 C 0.8860(3) 0.3077(3) 0.22650(15) 0.0350(4) Uani 1 1 d . . . . .
C5 C 0.6113(3) 0.4188(3) 0.14739(15) 0.0379(4) Uani 1 1 d . . . . .
C3 C 0.4737(3) 0.8203(4) 0.18039(18) 0.0474(5) Uani 1 1 d . . . . .
H3A H 0.397335 0.736418 0.132873 0.057 Uiso 1 1 calc R U . . .
H3B H 0.462315 0.947414 0.149517 0.057 Uiso 1 1 calc R U . . .
C1 C 0.4486(2) 0.6290(4) 0.34741(16) 0.0426(4) Uani 1 1 d . . . . .
H1A H 0.433866 0.638979 0.424108 0.051 Uiso 1 1 calc R U . . .
H1B H 0.362704 0.539461 0.312485 0.051 Uiso 1 1 calc R U . . .
C2 C 0.4192(3) 0.8218(4) 0.29309(19) 0.0482(5) Uani 1 1 d . . . . .
H2A H 0.296657 0.855202 0.287256 0.058 Uiso 1 1 calc R U . . .
H2B H 0.485851 0.917262 0.337984 0.058 Uiso 1 1 calc R U . . .
C12 C 0.8039(3) 0.1788(3) 0.3055(2) 0.0475(5) Uani 1 1 d . . . . .
H12A H 0.868642 0.189638 0.377815 0.071 Uiso 1 1 calc R U . . .
H12B H 0.806505 0.049197 0.281203 0.071 Uiso 1 1 calc R U . . .
H12C H 0.685234 0.216855 0.307142 0.071 Uiso 1 1 calc R U . . .
C13 C 1.0694(3) 0.2305(3) 0.2197(2) 0.0494(5) Uani 1 1 d . . . . .
H13A H 1.124123 0.307176 0.169858 0.074 Uiso 1 1 calc R U . . .
H13B H 1.061048 0.101452 0.193904 0.074 Uiso 1 1 calc R U . . .
H13C H 1.137727 0.234517 0.291134 0.074 Uiso 1 1 calc R U . . .
C11 C 0.8662(3) 0.4826(4) 0.05430(16) 0.0478(5) Uani 1 1 d . . . . .
H11A H 0.951734 0.425947 0.013754 0.057 Uiso 1 1 calc R U . . .
H11B H 0.784189 0.556368 0.004186 0.057 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 1.4387(16) . ?
S1 O2 1.4335(16) . ?
S1 N1 1.6613(15) . ?
S1 C9 1.7850(16) . ?
O3 C4 1.419(2) . ?
O3 C3 1.447(3) . ?
O4 C5 1.206(3) . ?
N1 C4 1.446(2) . ?
N1 C1 1.482(2) . ?
C4 C8 1.552(2) . ?
C4 C5 1.562(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.519(2) . ?
C8 C10 1.536(2) . ?
C8 C7 1.575(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.554(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.557(3) . ?
C6 C5 1.503(3) . ?
C6 C11 1.555(3) . ?
C7 C12 1.532(3) . ?
C7 C13 1.534(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.508(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 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 N1 111.38(9) . . ?
O1 S1 C9 111.34(9) . . ?
O2 S1 O1 115.70(11) . . ?
O2 S1 N1 108.94(9) . . ?
O2 S1 C9 111.41(10) . . ?
N1 S1 C9 96.38(7) . . ?
C4 O3 C3 113.87(15) . . ?
C4 N1 S1 112.41(11) . . ?
C4 N1 C1 116.76(15) . . ?
C1 N1 S1 117.10(12) . . ?
O3 C4 N1 112.74(13) . . ?
O3 C4 C8 110.75(13) . . ?
O3 C4 C5 109.22(14) . . ?
N1 C4 C8 106.94(13) . . ?
N1 C4 C5 115.03(14) . . ?
C8 C4 C5 101.55(13) . . ?
S1 C9 H9A 110.5 . . ?
S1 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C8 C9 S1 106.33(11) . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
C4 C8 C7 102.88(13) . . ?
C9 C8 C4 107.81(13) . . ?
C9 C8 C10 118.07(14) . . ?
C9 C8 C7 118.10(15) . . ?
C10 C8 C4 106.85(14) . . ?
C10 C8 C7 101.66(15) . . ?
C8 C10 H10A 111.3 . . ?
C8 C10 H10B 111.3 . . ?
C8 C10 C11 102.43(16) . . ?
H10A C10 H10B 109.2 . . ?
C11 C10 H10A 111.3 . . ?
C11 C10 H10B 111.3 . . ?
C7 C6 H6 115.0 . . ?
C5 C6 H6 115.0 . . ?
C5 C6 C7 99.95(14) . . ?
C5 C6 C11 107.20(18) . . ?
C11 C6 H6 115.0 . . ?
C11 C6 C7 103.10(16) . . ?
C6 C7 C8 92.95(14) . . ?
C12 C7 C8 116.62(16) . . ?
C12 C7 C6 112.68(17) . . ?
C12 C7 C13 107.26(18) . . ?
C13 C7 C8 113.43(16) . . ?
C13 C7 C6 113.64(16) . . ?
O4 C5 C4 126.2(2) . . ?
O4 C5 C6 128.93(18) . . ?
C6 C5 C4 104.88(15) . . ?
O3 C3 H3A 109.4 . . ?
O3 C3 H3B 109.4 . . ?
O3 C3 C2 111.04(17) . . ?
H3A C3 H3B 108.0 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.61(16) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C3 C2 C1 110.88(18) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C11 C6 104.08(15) . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C6 C11 H11A 110.9 . . ?
C6 C11 H11B 110.9 . . ?
H11A C11 H11B 109.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.548
_oxdiff_exptl_absorpt_empirical_full_min 0.555
