# Electronic Supplementary Material (ESI) for Inorganic 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_1
_database_code_depnum_ccdc_archive 'CCDC 2190548'
loop_
_audit_author_name
_audit_author_address
'Ying Wang'
;College of Chemistry and Environmental Science, Hebei University
China
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V95 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C H6 N3 O4 S'
_chemical_formula_moiety         ?
_chemical_formula_weight         156.15
_chemical_melting_point          ?
_chemical_absolute_configuration ?
_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                   8.9377(3)
_cell_length_b                   8.9377(3)
_cell_length_c                   15.6032(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1246.42(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1221
_cell_measurement_theta_min      2.6265
_cell_measurement_theta_max      20.695
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             648
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      273(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            12665
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.1408
_diffrn_reflns_theta_min         2.626
_diffrn_reflns_theta_max         24.385
_diffrn_reflns_theta_full        24.385
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1031
_reflns_number_gt                839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.576
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       'Bruker BIS V6.2.14/2020-04-30'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+0.1506P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1031
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;

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'

_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_
_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 0.77780(15) 0.60300(15) 0.09383(8) 0.0305(4) Uani 1 1 d . . . . .
O1 O 0.7418(4) 0.7635(4) 0.04626(19) 0.0332(9) Uani 1 1 d . . . . .
O2 O 0.6758(5) 0.4956(4) 0.0585(2) 0.0411(11) Uani 1 1 d . . . . .
O3 O 0.9306(4) 0.5697(5) 0.0752(3) 0.0575(12) Uani 1 1 d . . . . .
O4 O 0.7469(4) 0.6482(4) 0.17975(19) 0.0463(11) Uani 1 1 d . . . . .
N1 N 0.5658(6) 0.8338(5) 0.3173(3) 0.0661(17) Uani 1 1 d . . . . .
H1A H 0.616310 0.826952 0.270536 0.079 Uiso 1 1 calc R U . . .
H1B H 0.534323 0.919588 0.334508 0.079 Uiso 1 1 calc R U . . .
N2 N 0.4576(6) 0.7249(6) 0.4340(3) 0.0609(15) Uani 1 1 d . . . . .
H2A H 0.425744 0.810800 0.450772 0.073 Uiso 1 1 calc R U . . .
H2B H 0.438315 0.646164 0.463745 0.073 Uiso 1 1 calc R U . . .
N3 N 0.5843(6) 0.5813(5) 0.3366(3) 0.0564(14) Uani 1 1 d . . . . .
H3A H 0.634859 0.573238 0.289991 0.068 Uiso 1 1 calc R U . . .
H3B H 0.564587 0.502994 0.366635 0.068 Uiso 1 1 calc R U . . .
C1 C 0.5368(7) 0.7136(7) 0.3622(4) 0.0425(15) Uani 1 1 d . . . . .

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 0.0346(8) 0.0304(8) 0.0265(7) 0.0019(7) -0.0013(6) 0.0007(7)
O1 0.050(2) 0.0275(19) 0.0224(15) -0.0003(16) -0.0059(17) -0.0021(19)
O2 0.056(3) 0.029(2) 0.037(2) 0.0031(18) -0.0087(19) -0.0131(17)
O3 0.034(3) 0.077(3) 0.062(3) 0.014(2) 0.002(2) 0.015(2)
O4 0.074(3) 0.046(2) 0.0194(19) -0.0028(17) 0.0016(19) -0.001(2)
N1 0.094(5) 0.037(3) 0.067(4) 0.010(3) 0.035(3) 0.007(3)
N2 0.076(4) 0.052(4) 0.055(3) 0.000(3) 0.031(3) -0.001(3)
N3 0.078(4) 0.039(3) 0.052(3) 0.001(3) 0.022(3) 0.005(3)
C1 0.044(4) 0.044(4) 0.039(4) -0.001(3) 0.011(3) -0.004(3)

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 O4 1.427(3) . ?
S1 O3 1.427(4) . ?
S1 O2 1.434(4) . ?
S1 O1 1.647(3) . ?
O1 O1 1.470(6) 7 ?
N1 C1 1.308(7) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C1 1.330(7) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C1 1.318(7) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?

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
O4 S1 O3 115.8(2) . . ?
O4 S1 O2 115.3(2) . . ?
O3 S1 O2 113.0(3) . . ?
O4 S1 O1 98.01(18) . . ?
O3 S1 O1 106.1(2) . . ?
O2 S1 O1 106.60(19) . . ?
O1 O1 S1 107.6(3) 7 . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N1 C1 N3 120.7(5) . . ?
N1 C1 N2 119.7(6) . . ?
N3 C1 N2 119.6(6) . . ?

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
O4 S1 O1 O1 -178.7(2) . . . 7 ?
O3 S1 O1 O1 61.5(3) . . . 7 ?
O2 S1 O1 O1 -59.2(3) . . . 7 ?

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
N1 H1A O4 0.86 2.43 3.159(6) 142.4 . yes
N1 H1B O3 0.86 2.15 2.952(6) 154.1 8_675 yes
N2 H2A O3 0.86 2.35 3.093(6) 145.2 8_675 yes
N2 H2A O4 0.86 2.48 3.058(6) 125.0 6_465 yes
N2 H2B O2 0.86 2.20 3.013(6) 158.0 2_665 yes
N3 H3A O4 0.86 2.10 2.909(6) 156.6 . yes
N3 H3B S1 0.86 2.99 3.779(5) 154.0 8_665 yes
N3 H3B O2 0.86 2.05 2.910(6) 175.9 8_665 yes

_shelx_res_file                  
;
TITL 1_a.res in P4(1)2(1)2
    1.res
    created by SHELXL-2018/3 at 17:50:38 on 16-Mar-2022
REM Old TITL 1 in P4(3)2(1)2
REM SHELXT solution in P4(1)2(1)2: R1 0.120, Rweak 0.030, Alpha 0.005
REM <I/s> 0.412 for 18 systematic absences, Orientation as input
REM Flack x = 0.198 ( 0.101 ) from 264 Parsons' quotients
REM Formula found by SHELXT: C4 O4 S
CELL 0.71073 8.9377 8.9377 15.6032 90 90 90
ZERR 8 0.0003 0.0003 0.001 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5-Y,0.5+X,0.25+Z
SYMM 0.5+Y,0.5-X,0.75+Z
SYMM 0.5-X,0.5+Y,0.25-Z
SYMM 0.5+X,0.5-Y,0.75-Z
SYMM +Y,+X,-Z
SYMM -Y,-X,0.5-Z
SFAC C H N O S
UNIT 8 48 24 32 8
twin
L.S. 10
PLAN  40
TEMP 0
CONF
htab
HTAB N1 O4
EQIV $2 -y+1, -x+2, -z+1/2
HTAB N1 O3_$2
HTAB N2 O3_$2
EQIV $3 x-1/2, -y+3/2, -z+3/4
HTAB N2 O4_$3
EQIV $4 -x+1, -y+1, z+1/2
HTAB N2 O2_$4
HTAB N3 O4
EQIV $5 -y+1, -x+1, -z+1/2
HTAB N3 S1_$5
HTAB N3 O2_$5
BOND
acta
list 4
fmap 2
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>

WGHT    0.035200    0.150600
BASF   0.09977
FVAR       0.60324
S1    5    0.777803    0.603000    0.093828    11.00000    0.03459    0.03036 =
         0.02650    0.00189   -0.00127    0.00069
O1    4    0.741764    0.763469    0.046262    11.00000    0.04980    0.02752 =
         0.02238   -0.00034   -0.00587   -0.00214
O2    4    0.675825    0.495566    0.058511    11.00000    0.05650    0.02933 =
         0.03737    0.00306   -0.00874   -0.01306
O3    4    0.930565    0.569653    0.075211    11.00000    0.03394    0.07691 =
         0.06166    0.01445    0.00218    0.01529
O4    4    0.746941    0.648151    0.179748    11.00000    0.07383    0.04574 =
         0.01944   -0.00276    0.00164   -0.00068
N1    3    0.565789    0.833774    0.317282    11.00000    0.09416    0.03697 =
         0.06707    0.01000    0.03516    0.00653
AFIX  93
H1A   2    0.616310    0.826952    0.270536    11.00000   -1.20000
H1B   2    0.534323    0.919588    0.334508    11.00000   -1.20000
AFIX   0
N2    3    0.457638    0.724857    0.434021    11.00000    0.07583    0.05226 =
         0.05468    0.00016    0.03080   -0.00076
AFIX  93
H2A   2    0.425744    0.810800    0.450772    11.00000   -1.20000
H2B   2    0.438315    0.646164    0.463745    11.00000   -1.20000
AFIX   0
N3    3    0.584250    0.581288    0.336641    11.00000    0.07761    0.03931 =
         0.05224    0.00140    0.02245    0.00481
AFIX  93
H3A   2    0.634859    0.573238    0.289991    11.00000   -1.20000
H3B   2    0.564587    0.502994    0.366635    11.00000   -1.20000
AFIX   0
C1    1    0.536814    0.713649    0.362173    11.00000    0.04431    0.04411 =
         0.03919   -0.00117    0.01084   -0.00415
HKLF 4




REM  1_a.res in P4(1)2(1)2
REM wR2 = 0.0905, GooF = S = 1.105, Restrained GooF = 1.105 for all data
REM R1 = 0.0448 for 839 Fo > 4sig(Fo) and 0.0648 for all 1031 data
REM 83 parameters refined using 0 restraints

END

WGHT      0.0352      0.1506

REM Instructions for potential hydrogen bonds
HTAB N1 O4
HTAB N1 O3_$2
HTAB N2 O3_$2
HTAB N2 O4_$3
HTAB N2 O2_$4
HTAB N3 O4
HTAB N3 S1_$5
HTAB N3 O2_$5

REM Highest difference peak  0.233,  deepest hole -0.281,  1-sigma level  0.068
Q1    1   0.4955  0.7088  0.4970  11.00000  0.05    0.23
Q2    1   0.3015  0.6985  0.2500  10.50000  0.05    0.22
Q3    1   0.7012  0.6106  0.2590  11.00000  0.05    0.21
Q4    1   0.5964  0.7061  0.1470  11.00000  0.05    0.20
Q5    1   1.0185  0.6028  0.0973  11.00000  0.05    0.20
Q6    1   0.7193  0.6401  0.2509  11.00000  0.05    0.20
Q7    1   0.7515  0.9020  0.3429  11.00000  0.05    0.19
Q8    1   0.7176  1.0011  0.3849  11.00000  0.05    0.18
Q9    1   0.3021  0.5630  0.3619  11.00000  0.05    0.18
Q10   1   0.5029  0.8452  0.4997  11.00000  0.05    0.18
Q11   1   0.7216  0.5090  0.0135  11.00000  0.05    0.18
Q12   1   0.7862  0.5177 -0.0436  11.00000  0.05    0.18
Q13   1   0.4969  0.7054  0.1954  11.00000  0.05    0.17
Q14   1   0.6625  0.6625  0.5000  10.50000  0.05    0.17
Q15   1   0.7798  0.5456  0.3640  11.00000  0.05    0.17
Q16   1   0.6512  0.8045  0.5062  11.00000  0.05    0.17
Q17   1   0.7086  0.4894  0.4040  11.00000  0.05    0.17
Q18   1   0.4013  0.7799  0.2459  11.00000  0.05    0.16
Q19   1   0.7214  0.8303  0.2577  11.00000  0.05    0.16
Q20   1   0.9278  0.6836  0.0776  11.00000  0.05    0.16
Q21   1   0.4140  0.6549  0.5544  11.00000  0.05    0.16
Q22   1   0.6030  0.7199  0.2281  11.00000  0.05    0.16
Q23   1   1.0432  0.5444  0.0105  11.00000  0.05    0.15
Q24   1   0.3247  0.8398  0.3801  11.00000  0.05    0.15
Q25   1   0.6587  0.8210  0.0457  11.00000  0.05    0.15
Q26   1   0.8259  0.4806  0.2200  11.00000  0.05    0.15
Q27   1   0.4071  0.4923  0.3401  11.00000  0.05    0.15
Q28   1   0.8148  0.6195  0.2197  11.00000  0.05    0.15
Q29   1   0.5968  0.6974  0.0202  11.00000  0.05    0.15
Q30   1   0.6987  0.5801 -0.0023  11.00000  0.05    0.15
Q31   1   0.5673  0.7602  0.4999  11.00000  0.05    0.14
Q32   1   0.5628  0.8394  0.2455  11.00000  0.05    0.14
Q33   1   0.6384  0.7918  0.1979  11.00000  0.05    0.14
Q34   1   0.3991  0.9609  0.2794  11.00000  0.05    0.14
Q35   1   0.7688  0.7528  0.2217  11.00000  0.05    0.14
Q36   1   0.8631  0.6019  0.2150  11.00000  0.05    0.14
Q37   1   0.7230  0.8711  0.4308  11.00000  0.05    0.13
Q38   1   0.6188  0.5560  0.4428  11.00000  0.05    0.13
Q39   1   0.7761  0.7761  0.0000  10.50000  0.05    0.13
Q40   1   0.5000  0.9595  0.2404  11.00000  0.05    0.13
;
_shelx_res_checksum              99633
