# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1961174'
loop_
_audit_author_name
_audit_author_address
'Feng Li'
;Shangqiu Normal University
China
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2021-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 N2 O4 S'
_chemical_formula_weight         268.29

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4413(11)
_cell_length_b                   8.9170(13)
_cell_length_c                   9.0986(11)
_cell_angle_alpha                95.122(5)
_cell_angle_beta                 107.332(5)
_cell_angle_gamma                113.574(4)
_cell_volume                     581.95(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5799
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10933
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         27.57
_reflns_number_total             2643
_reflns_number_gt                2239
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.1831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.85809(5) 0.35714(5) 0.70064(4) 0.03336(12) Uani 1 1 d . . .
N1 N 0.55503(17) 0.25786(14) 0.27213(13) 0.0316(3) Uani 1 1 d . . .
O1 O 0.98975(14) 0.54182(13) 0.68742(13) 0.0367(3) Uani 1 1 d . . .
O2 O 0.98231(17) 0.28683(16) 0.75602(15) 0.0499(3) Uani 1 1 d . . .
N2 N 0.72491(17) 0.25936(15) 0.52075(14) 0.0329(3) Uani 1 1 d . . .
O3 O 0.75710(16) 0.37742(16) 0.79484(13) 0.0461(3) Uani 1 1 d . . .
C1 C 0.3779(3) 0.2553(2) 0.00573(19) 0.0497(4) Uani 1 1 d . . .
H4 H 0.3012 0.2927 0.0443 0.060 Uiso 1 1 calc R . .
H5 H 0.3870 0.2975 -0.0876 0.060 Uiso 1 1 calc R . .
O4 O 0.29445(18) 0.07618(15) -0.03506(13) 0.0507(3) Uani 1 1 d . . .
C2 C 0.5686(2) 0.32428(19) 0.13175(17) 0.0378(3) Uani 1 1 d . . .
H14 H 0.6474 0.2920 0.0914 0.045 Uiso 1 1 calc R . .
H13 H 0.6237 0.4463 0.1605 0.045 Uiso 1 1 calc R . .
C3 C 0.67209(18) 0.34402(16) 0.42105(15) 0.0265(3) Uani 1 1 d . . .
C4 C 0.73282(18) 0.52647(16) 0.46974(16) 0.0264(3) Uani 1 1 d . . .
C5 C 0.89233(19) 0.62139(17) 0.60317(16) 0.0295(3) Uani 1 1 d . . .
C6 C 0.9605(2) 0.79277(19) 0.65599(19) 0.0391(4) Uani 1 1 d . . .
H12 H 1.0702 0.8537 0.7432 0.047 Uiso 1 1 calc R . .
C7 C 0.8630(2) 0.87229(19) 0.5771(2) 0.0433(4) Uani 1 1 d . . .
H2 H 0.9087 0.9883 0.6097 0.052 Uiso 1 1 calc R . .
C8 C 0.4633(2) 0.07303(18) 0.23230(18) 0.0392(4) Uani 1 1 d . . .
H9 H 0.4460 0.0325 0.3245 0.047 Uiso 1 1 calc R . .
H6 H 0.5394 0.0304 0.1989 0.047 Uiso 1 1 calc R . .
C9 C 0.2770(2) 0.0117(2) 0.09974(19) 0.0460(4) Uani 1 1 d . . .
H7 H 0.2177 -0.1104 0.0691 0.055 Uiso 1 1 calc R . .
H8 H 0.1980 0.0462 0.1378 0.055 Uiso 1 1 calc R . .
C10 C 0.6321(2) 0.60905(18) 0.39648(18) 0.0328(3) Uani 1 1 d . . .
H10 H 0.5204 0.5479 0.3114 0.039 Uiso 1 1 calc R . .
C11 C 0.6970(2) 0.7802(2) 0.4492(2) 0.0406(4) Uani 1 1 d . . .
H11 H 0.6295 0.8340 0.3991 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.03283(19) 0.0353(2) 0.02823(19) 0.00855(14) 0.00543(14) 0.01563(15)
N1 0.0367(6) 0.0237(6) 0.0247(6) 0.0043(4) 0.0063(5) 0.0081(5)
O1 0.0274(5) 0.0353(5) 0.0364(5) 0.0060(4) 0.0032(4) 0.0103(4)
O2 0.0484(7) 0.0524(7) 0.0478(7) 0.0155(6) 0.0041(5) 0.0305(6)
N2 0.0362(6) 0.0273(6) 0.0289(6) 0.0057(5) 0.0059(5) 0.0128(5)
O3 0.0458(6) 0.0605(8) 0.0326(6) 0.0129(5) 0.0154(5) 0.0233(6)
C1 0.0592(11) 0.0417(9) 0.0301(8) 0.0087(7) 0.0022(7) 0.0156(8)
O4 0.0580(7) 0.0414(6) 0.0259(5) 0.0000(5) 0.0032(5) 0.0071(6)
C2 0.0462(8) 0.0327(7) 0.0268(7) 0.0076(6) 0.0124(6) 0.0109(7)
C3 0.0253(6) 0.0257(6) 0.0261(6) 0.0056(5) 0.0091(5) 0.0096(5)
C4 0.0269(6) 0.0241(6) 0.0274(6) 0.0057(5) 0.0119(5) 0.0094(5)
C5 0.0278(6) 0.0291(7) 0.0294(7) 0.0043(5) 0.0110(5) 0.0108(5)
C6 0.0382(8) 0.0294(7) 0.0363(8) -0.0029(6) 0.0132(7) 0.0048(6)
C7 0.0585(10) 0.0237(7) 0.0521(10) 0.0064(6) 0.0321(8) 0.0146(7)
C8 0.0505(9) 0.0242(7) 0.0320(7) 0.0035(6) 0.0086(7) 0.0116(6)
C9 0.0482(9) 0.0341(8) 0.0339(8) 0.0015(6) 0.0088(7) 0.0034(7)
C10 0.0333(7) 0.0343(7) 0.0342(7) 0.0116(6) 0.0142(6) 0.0165(6)
C11 0.0521(9) 0.0355(8) 0.0504(9) 0.0186(7) 0.0282(8) 0.0264(7)

_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 1.4191(12) . ?
S1 O3 1.4230(12) . ?
S1 N2 1.6024(12) . ?
S1 O1 1.6163(11) . ?
N1 C3 1.3460(17) . ?
N1 C8 1.4671(18) . ?
N1 C2 1.4708(18) . ?
O1 C5 1.3984(17) . ?
N2 C3 1.3199(18) . ?
C1 O4 1.422(2) . ?
C1 C2 1.506(2) . ?
C1 H4 0.9700 . ?
C1 H5 0.9700 . ?
O4 C9 1.422(2) . ?
C2 H14 0.9700 . ?
C2 H13 0.9700 . ?
C3 C4 1.4747(18) . ?
C4 C5 1.3908(19) . ?
C4 C10 1.3999(19) . ?
C5 C6 1.378(2) . ?
C6 C7 1.379(2) . ?
C6 H12 0.9300 . ?
C7 C11 1.389(2) . ?
C7 H2 0.9300 . ?
C8 C9 1.513(2) . ?
C8 H9 0.9700 . ?
C8 H6 0.9700 . ?
C9 H7 0.9700 . ?
C9 H8 0.9700 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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 O3 118.54(8) . . ?
O2 S1 N2 109.14(7) . . ?
O3 S1 N2 111.98(7) . . ?
O2 S1 O1 103.87(7) . . ?
O3 S1 O1 107.98(7) . . ?
N2 S1 O1 104.02(6) . . ?
C3 N1 C8 120.08(12) . . ?
C3 N1 C2 123.27(12) . . ?
C8 N1 C2 111.59(11) . . ?
C5 O1 S1 113.95(8) . . ?
C3 N2 S1 119.15(10) . . ?
O4 C1 C2 110.15(14) . . ?
O4 C1 H4 109.6 . . ?
C2 C1 H4 109.6 . . ?
O4 C1 H5 109.6 . . ?
C2 C1 H5 109.6 . . ?
H4 C1 H5 108.1 . . ?
C9 O4 C1 110.47(12) . . ?
N1 C2 C1 109.59(13) . . ?
N1 C2 H14 109.8 . . ?
C1 C2 H14 109.8 . . ?
N1 C2 H13 109.8 . . ?
C1 C2 H13 109.8 . . ?
H14 C2 H13 108.2 . . ?
N2 C3 N1 117.97(12) . . ?
N2 C3 C4 122.03(12) . . ?
N1 C3 C4 119.98(12) . . ?
C5 C4 C10 117.33(13) . . ?
C5 C4 C3 118.63(12) . . ?
C10 C4 C3 123.87(12) . . ?
C6 C5 C4 122.57(14) . . ?
C6 C5 O1 118.02(13) . . ?
C4 C5 O1 119.41(12) . . ?
C5 C6 C7 118.72(14) . . ?
C5 C6 H12 120.6 . . ?
C7 C6 H12 120.6 . . ?
C6 C7 C11 120.42(14) . . ?
C6 C7 H2 119.8 . . ?
C11 C7 H2 119.8 . . ?
N1 C8 C9 108.57(13) . . ?
N1 C8 H9 110.0 . . ?
C9 C8 H9 110.0 . . ?
N1 C8 H6 110.0 . . ?
C9 C8 H6 110.0 . . ?
H9 C8 H6 108.4 . . ?
O4 C9 C8 112.05(14) . . ?
O4 C9 H7 109.2 . . ?
C8 C9 H7 109.2 . . ?
O4 C9 H8 109.2 . . ?
C8 C9 H8 109.2 . . ?
H7 C9 H8 107.9 . . ?
C11 C10 C4 120.68(14) . . ?
C11 C10 H10 119.7 . . ?
C4 C10 H10 119.7 . . ?
C10 C11 C7 120.06(15) . . ?
C10 C11 H11 120.0 . . ?
C7 C11 H11 120.0 . . ?

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 O1 C5 167.05(10) . . . . ?
O3 S1 O1 C5 -66.25(11) . . . . ?
N2 S1 O1 C5 52.87(11) . . . . ?
O2 S1 N2 C3 -144.72(12) . . . . ?
O3 S1 N2 C3 82.01(13) . . . . ?
O1 S1 N2 C3 -34.35(13) . . . . ?
C2 C1 O4 C9 60.3(2) . . . . ?
C3 N1 C2 C1 -148.84(14) . . . . ?
C8 N1 C2 C1 56.42(18) . . . . ?
O4 C1 C2 N1 -58.31(19) . . . . ?
S1 N2 C3 N1 -177.72(10) . . . . ?
S1 N2 C3 C4 0.39(19) . . . . ?
C8 N1 C3 N2 11.2(2) . . . . ?
C2 N1 C3 N2 -141.49(15) . . . . ?
C8 N1 C3 C4 -166.93(13) . . . . ?
C2 N1 C3 C4 40.4(2) . . . . ?
N2 C3 C4 C5 21.3(2) . . . . ?
N1 C3 C4 C5 -160.64(13) . . . . ?
N2 C3 C4 C10 -153.87(14) . . . . ?
N1 C3 C4 C10 24.2(2) . . . . ?
C10 C4 C5 C6 -5.4(2) . . . . ?
C3 C4 C5 C6 179.13(13) . . . . ?
C10 C4 C5 O1 175.20(12) . . . . ?
C3 C4 C5 O1 -0.27(19) . . . . ?
S1 O1 C5 C6 142.37(12) . . . . ?
S1 O1 C5 C4 -38.21(16) . . . . ?
C4 C5 C6 C7 2.5(2) . . . . ?
O1 C5 C6 C7 -178.06(13) . . . . ?
C5 C6 C7 C11 1.5(2) . . . . ?
C3 N1 C8 C9 149.86(14) . . . . ?
C2 N1 C8 C9 -54.49(18) . . . . ?
C1 O4 C9 C8 -60.0(2) . . . . ?
N1 C8 C9 O4 56.19(19) . . . . ?
C5 C4 C10 C11 4.3(2) . . . . ?
C3 C4 C10 C11 179.55(13) . . . . ?
C4 C10 C11 C7 -0.5(2) . . . . ?
C6 C7 C11 C10 -2.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.039
