# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2132429'
loop_
_audit_author_name
_audit_author_address
'J. Jiang'
;Wenzhou University
China
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2022-04-01 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         'C15 H20 N2 O7 S'
_chemical_formula_sum            'C15 H20 N2 O7 S'
_chemical_formula_weight         372.39

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'

_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                   7.6579(14)
_cell_length_b                   8.4312(16)
_cell_length_c                   14.441(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.161(3)
_cell_angle_gamma                90
_cell_volume                     907.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4337
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.83

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   '(SADABS; Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7312
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.732
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3523
_reflns_number_gt                3290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.976

_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       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2018) and DIAMOND (Brandenburg, 2015)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, 2018) and and PLATON (Spek, 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)+(0.0717P)²+0.2191P] 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 1424 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration Unknow
_refine_ls_number_reflns         3523
_refine_ls_number_parameters     229
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.146
_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 1.19308(10) 0.07065(11) -0.06921(7) 0.0488(3) Uani 1 1 d . . . . .
O1 O 0.4989(8) 0.4521(7) -0.4385(3) 0.1241(19) Uani 1 1 d . . . . .
O2 O 0.5957(6) 0.5666(7) -0.3043(3) 0.0959(12) Uani 1 1 d . . . . .
O3 O 1.2276(4) 0.2278(4) -0.0350(3) 0.0714(9) Uani 1 1 d . . . . .
O4 O 1.3139(4) -0.0531(4) -0.0273(3) 0.0735(10) Uani 1 1 d . . . . .
O5 O 0.9605(4) 0.1795(4) 0.12800(17) 0.0530(7) Uani 1 1 d . . . . .
O6 O 0.8809(9) -0.0647(5) 0.3031(3) 0.126(2) Uani 1 1 d . . . . .
O7 O 0.8217(4) 0.1899(4) 0.31404(18) 0.0597(8) Uani 1 1 d . . . . .
N1 N 0.5643(6) 0.4488(7) -0.3540(3) 0.0795(14) Uani 1 1 d . . . . .
N2 N 0.9975(4) 0.0204(3) -0.05596(19) 0.0386(6) Uani 1 1 d . . . . .
H2 H 0.979355 -0.075585 -0.040287 0.046 Uiso 1 1 calc R U . . .
C1 C 0.7018(5) 0.2890(5) -0.2151(2) 0.0451(8) Uani 1 1 d . . . . .
H1 H 0.740609 0.382279 -0.182535 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6025(5) 0.2921(6) -0.3082(3) 0.0560(10) Uani 1 1 d . . . . .
C3 C 0.5438(6) 0.1574(8) -0.3592(3) 0.0715(14) Uani 1 1 d . . . . .
H3 H 0.479883 0.163702 -0.422079 0.086 Uiso 1 1 calc R U . . .
C4 C 0.5815(6) 0.0142(7) -0.3154(3) 0.0683(13) Uani 1 1 d . . . . .
H4 H 0.540035 -0.078382 -0.348055 0.082 Uiso 1 1 calc R U . . .
C5 C 0.6809(6) 0.0058(5) -0.2229(3) 0.0552(10) Uani 1 1 d . . . . .
H5 H 0.707619 -0.092789 -0.194357 0.066 Uiso 1 1 calc R U . . .
C6 C 0.7414(4) 0.1420(4) -0.1719(2) 0.0386(7) Uani 1 1 d . . . . .
C7 C 0.8490(4) 0.1354(4) -0.0701(2) 0.0350(6) Uani 1 1 d . . . . .
H7 H 0.900255 0.240828 -0.053046 0.042 Uiso 1 1 calc R U . . .
C8 C 0.7279(4) 0.0949(4) -0.0031(2) 0.0373(7) Uani 1 1 d . . . . .
H8A H 0.620848 0.160073 -0.019315 0.045 Uiso 1 1 calc R U . . .
H8B H 0.690911 -0.015031 -0.012758 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8154(4) 0.1193(4) 0.1007(2) 0.0405(7) Uani 1 1 d . . . . .
C10 C 0.7031(6) 0.0652(7) 0.1682(3) 0.0630(10) Uani 1 1 d . . . . .
H10A H 0.651854 -0.037839 0.148233 0.076 Uiso 1 1 calc R U . . .
H10B H 0.605134 0.139266 0.165619 0.076 Uiso 1 1 calc R U . . .
C11 C 0.8125(7) 0.0543(6) 0.2692(3) 0.0640(11) Uani 1 1 d . . . . .
C12 C 0.9311(7) 0.1963(6) 0.4115(3) 0.0688(11) Uani 1 1 d . U . . .
H12 H 0.958881 0.089122 0.436962 0.083 Uiso 1 1 calc R U . . .
C13 C 0.8213(10) 0.2848(11) 0.4685(4) 0.108(2) Uani 1 1 d . U . . .
H13A H 0.862511 0.258911 0.534593 0.162 Uiso 1 1 calc R U . . .
H13B H 0.697552 0.255339 0.447409 0.162 Uiso 1 1 calc R U . . .
H13C H 0.833757 0.396809 0.459832 0.162 Uiso 1 1 calc R U . . .
C14 C 1.0967(10) 0.2839(14) 0.4104(6) 0.124(2) Uani 1 1 d . U . . .
H14A H 1.163035 0.228306 0.371575 0.187 Uiso 1 1 calc R U . . .
H14B H 1.168273 0.292697 0.474010 0.187 Uiso 1 1 calc R U . . .
H14C H 1.066733 0.388056 0.384706 0.187 Uiso 1 1 calc R U . . .
C15 C 1.1854(7) 0.0737(8) -0.1911(4) 0.0776(13) Uani 1 1 d . . . . .
H15A H 1.106961 0.157142 -0.220741 0.116 Uiso 1 1 calc R U . . .
H15B H 1.141343 -0.026255 -0.218745 0.116 Uiso 1 1 calc R U . . .
H15C H 1.303671 0.091865 -0.200879 0.116 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 O3 1.417(3) . ?
S1 O4 1.434(3) . ?
S1 N2 1.609(3) . ?
S1 C15 1.749(5) . ?
O1 N1 1.211(6) . ?
O2 N1 1.216(7) . ?
O5 C9 1.204(4) . ?
O6 C11 1.186(6) . ?
O7 C11 1.308(5) . ?
O7 C12 1.466(5) . ?
N1 C2 1.476(7) . ?
N2 C7 1.473(4) . ?
N2 H2 0.8600 . ?
C1 C2 1.386(5) . ?
C1 C6 1.389(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(8) . ?
C3 C4 1.363(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(4) . ?
C7 C8 1.525(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.510(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.510(5) . ?
C10 C11 1.510(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C14 1.471(10) . ?
C12 C13 1.502(9) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O3 S1 O4 118.8(2) . . ?
O3 S1 N2 108.02(18) . . ?
O4 S1 N2 106.65(17) . . ?
O3 S1 C15 107.3(3) . . ?
O4 S1 C15 107.8(3) . . ?
N2 S1 C15 107.7(2) . . ?
C11 O7 C12 117.5(4) . . ?
O1 N1 O2 123.9(5) . . ?
O1 N1 C2 117.8(6) . . ?
O2 N1 C2 118.3(4) . . ?
C7 N2 S1 121.3(2) . . ?
C7 N2 H2 119.3 . . ?
S1 N2 H2 119.3 . . ?
C2 C1 C6 117.9(4) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C3 C2 C1 123.0(4) . . ?
C3 C2 N1 119.5(4) . . ?
C1 C2 N1 117.4(5) . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 121.9(3) . . ?
C1 C6 C7 118.9(3) . . ?
N2 C7 C6 113.0(2) . . ?
N2 C7 C8 109.0(2) . . ?
C6 C7 C8 110.5(2) . . ?
N2 C7 H7 108.0 . . ?
C6 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C9 C8 C7 113.8(3) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O5 C9 C10 122.4(3) . . ?
O5 C9 C8 123.4(3) . . ?
C10 C9 C8 114.2(3) . . ?
C9 C10 C11 111.7(3) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O6 C11 O7 124.5(4) . . ?
O6 C11 C10 123.1(5) . . ?
O7 C11 C10 112.4(4) . . ?
O7 C12 C14 108.2(5) . . ?
O7 C12 C13 106.0(4) . . ?
C14 C12 C13 110.4(6) . . ?
O7 C12 H12 110.7 . . ?
C14 C12 H12 110.7 . . ?
C13 C12 H12 110.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O3 S1 N2 C7 36.7(3) . . . . ?
O4 S1 N2 C7 165.5(3) . . . . ?
C15 S1 N2 C7 -78.9(3) . . . . ?
C6 C1 C2 C3 -0.6(6) . . . . ?
C6 C1 C2 N1 -178.8(3) . . . . ?
O1 N1 C2 C3 -7.9(7) . . . . ?
O2 N1 C2 C3 170.2(5) . . . . ?
O1 N1 C2 C1 170.4(5) . . . . ?
O2 N1 C2 C1 -11.5(6) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
N1 C2 C3 C4 179.7(4) . . . . ?
C2 C3 C4 C5 -1.9(7) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C2 C1 C6 C7 -179.8(3) . . . . ?
S1 N2 C7 C6 89.1(3) . . . . ?
S1 N2 C7 C8 -147.7(2) . . . . ?
C5 C6 C7 N2 47.9(4) . . . . ?
C1 C6 C7 N2 -132.4(3) . . . . ?
C5 C6 C7 C8 -74.6(4) . . . . ?
C1 C6 C7 C8 105.1(3) . . . . ?
N2 C7 C8 C9 67.3(3) . . . . ?
C6 C7 C8 C9 -167.9(3) . . . . ?
C7 C8 C9 O5 6.8(5) . . . . ?
C7 C8 C9 C10 -174.6(3) . . . . ?
O5 C9 C10 C11 -15.5(6) . . . . ?
C8 C9 C10 C11 165.9(4) . . . . ?
C12 O7 C11 O6 2.9(8) . . . . ?
C12 O7 C11 C10 -177.4(4) . . . . ?
C9 C10 C11 O6 -94.2(7) . . . . ?
C9 C10 C11 O7 86.0(5) . . . . ?
C11 O7 C12 C14 106.5(6) . . . . ?
C11 O7 C12 C13 -135.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14 H14A O2 0.96 2.65 3.592(10) 166.0 2_745 yes
C8 H8B O3 0.97 2.32 3.149(4) 143.3 2_745 yes
C8 H8A O4 0.97 2.53 3.027(5) 111.8 2_755 yes
N2 H2 O5 0.86 2.52 3.098(4) 125.4 2_745 yes
N2 H2 O5 0.86 2.52 3.098(4) 125.4 2_745 yes
C8 H8A O4 0.97 2.53 3.027(5) 111.8 2_755 yes
C8 H8B O3 0.97 2.32 3.149(4) 143.3 2_745 yes
C14 H14A O2 0.96 2.65 3.592(10) 166.0 2_745 yes

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.047

