# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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 2270364'
loop_
_audit_author_name
_audit_author_address
'Ying Wang'
;College of Chemistry and Environmental Science, Hebei University
China
;
_audit_update_record             
;
2023-06-16 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V102 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            'C1.50 H4.50 N3.50 O1.50 S0.50'
_chemical_formula_moiety         ?
_chemical_formula_weight         111.62
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.146(2)
_cell_length_b                   7.852(3)
_cell_length_c                   10.511(4)
_cell_angle_alpha                96.517(13)
_cell_angle_beta                 96.693(12)
_cell_angle_gamma                95.265(13)
_cell_volume                     416.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2798
_cell_measurement_theta_min      3.077
_cell_measurement_theta_max      24.6935
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_F_000             232
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_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            13826
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_theta_min         2.626
_diffrn_reflns_theta_max         28.251
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1988
_reflns_number_gt                1214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker BIS V6.2.14/2020-04-30'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXS (G. Sheldrick)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.1231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1988
_refine_ls_number_parameters     137
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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
C1 C 0.5140(5) 0.7750(3) 0.5894(2) 0.0254(6) Uani 1 1 d . . . . .
C2 C 0.2975(5) 0.6264(3) 0.4034(2) 0.0262(6) Uani 1 1 d . . . . .
C3 C 0.6809(5) 0.8157(3) 0.4032(2) 0.0262(6) Uani 1 1 d . . . . .
S1 S 0.14325(14) 0.75661(9) 0.01911(6) 0.0284(2) Uani 1 1 d . . . . .
O1 O 0.2650(4) 0.9252(2) 0.07626(18) 0.0408(5) Uani 1 1 d . . . . .
O2 O 0.1390(4) 0.7274(3) -0.11927(17) 0.0418(6) Uani 1 1 d . . . . .
O3 O 0.2553(4) 0.6185(2) 0.08195(17) 0.0338(5) Uani 1 1 d . . . . .
N1 N 0.5305(5) 0.8116(3) 0.7158(2) 0.0369(6) Uani 1 1 d . . . . .
H1A H 0.415132 0.763521 0.757067 0.044 Uiso 1 1 calc R U . . .
H1B H 0.656614 0.883575 0.756924 0.044 Uiso 1 1 calc R U . . .
N2 N 0.3108(4) 0.6608(3) 0.53115(19) 0.0284(6) Uani 1 1 d . . . . .
N3 N 0.7033(4) 0.8534(3) 0.53052(19) 0.0283(6) Uani 1 1 d . . . . .
N4 N 0.1077(4) 0.5165(3) 0.3377(2) 0.0344(6) Uani 1 1 d . . . . .
H4A H -0.008892 0.466354 0.377234 0.041 Uiso 1 1 calc R U . . .
H4B H 0.100156 0.494800 0.255238 0.041 Uiso 1 1 calc R U . . .
N5 N 0.4782(4) 0.7040(3) 0.3378(2) 0.0297(6) Uani 1 1 d . . . . .
N6 N 0.8518(5) 0.8871(3) 0.3359(2) 0.0355(6) Uani 1 1 d . . . . .
H6A H 0.980320 0.959303 0.374445 0.043 Uiso 1 1 calc R U . . .
H6B H 0.834995 0.861481 0.253404 0.043 Uiso 1 1 calc R U . . .
H5 H 0.461(6) 0.686(4) 0.257(3) 0.035(8) Uiso 1 1 d . . . . .
N7 N -0.1605(5) 0.7513(3) 0.0550(2) 0.0314(6) Uani 1 1 d D . . . .
H7A H -0.238(5) 0.649(3) 0.022(3) 0.038 Uiso 1 1 d D U . . .
H7B H -0.237(5) 0.835(3) 0.021(3) 0.038 Uiso 1 1 d D U . . .

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
C1 0.0246(15) 0.0275(16) 0.0232(14) 0.0022(12) 0.0026(11) -0.0003(12)
C2 0.0259(15) 0.0270(16) 0.0243(14) 0.0020(12) 0.0011(11) -0.0002(12)
C3 0.0262(15) 0.0268(16) 0.0245(14) 0.0045(12) 0.0013(11) -0.0022(12)
S1 0.0267(4) 0.0337(4) 0.0215(4) -0.0005(3) 0.0027(3) -0.0083(3)
O1 0.0419(13) 0.0307(12) 0.0415(12) -0.0047(9) -0.0048(9) -0.0155(10)
O2 0.0408(13) 0.0614(15) 0.0197(10) 0.0013(9) 0.0068(8) -0.0126(11)
O3 0.0330(11) 0.0343(12) 0.0321(11) 0.0033(9) -0.0009(8) -0.0002(9)
N1 0.0346(15) 0.0491(17) 0.0220(12) -0.0039(11) 0.0041(10) -0.0130(12)
N2 0.0290(13) 0.0302(14) 0.0238(12) 0.0020(10) 0.0024(9) -0.0052(11)
N3 0.0275(13) 0.0335(14) 0.0215(12) 0.0012(10) 0.0020(9) -0.0055(11)
N4 0.0343(14) 0.0399(16) 0.0237(12) -0.0022(11) 0.0004(10) -0.0120(12)
N5 0.0316(14) 0.0362(15) 0.0185(12) 0.0005(11) 0.0022(10) -0.0071(11)
N6 0.0370(15) 0.0444(16) 0.0228(12) 0.0032(11) 0.0050(10) -0.0091(12)
N7 0.0284(14) 0.0329(16) 0.0314(13) 0.0012(11) 0.0042(10) -0.0013(11)

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
C1 N1 1.317(3) . ?
C1 N2 1.352(3) . ?
C1 N3 1.352(3) . ?
C2 N4 1.314(3) . ?
C2 N2 1.332(3) . ?
C2 N5 1.361(3) . ?
C3 N6 1.317(3) . ?
C3 N3 1.326(3) . ?
C3 N5 1.363(3) . ?
S1 O2 1.4438(19) . ?
S1 O1 1.444(2) . ?
S1 O3 1.461(2) . ?
S1 N7 1.648(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5 0.84(3) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 H7A 0.878(17) . ?
N7 H7B 0.883(17) . ?

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
N1 C1 N2 116.8(2) . . ?
N1 C1 N3 117.1(2) . . ?
N2 C1 N3 126.1(2) . . ?
N4 C2 N2 120.4(2) . . ?
N4 C2 N5 118.5(2) . . ?
N2 C2 N5 121.1(2) . . ?
N6 C3 N3 121.0(2) . . ?
N6 C3 N5 117.9(2) . . ?
N3 C3 N5 121.1(2) . . ?
O2 S1 O1 113.55(12) . . ?
O2 S1 O3 111.63(13) . . ?
O1 S1 O3 112.26(12) . . ?
O2 S1 N7 109.62(12) . . ?
O1 S1 N7 104.29(13) . . ?
O3 S1 N7 104.81(12) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C2 N2 C1 115.7(2) . . ?
C3 N3 C1 115.9(2) . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N5 C3 120.0(2) . . ?
C2 N5 H5 120(2) . . ?
C3 N5 H5 120(2) . . ?
C3 N6 H6A 120.0 . . ?
C3 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
S1 N7 H7A 106(2) . . ?
S1 N7 H7B 108.6(19) . . ?
H7A N7 H7B 112(3) . . ?

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
N4 C2 N2 C1 179.8(2) . . . . ?
N5 C2 N2 C1 -0.5(4) . . . . ?
N1 C1 N2 C2 179.7(2) . . . . ?
N3 C1 N2 C2 -1.1(4) . . . . ?
N6 C3 N3 C1 178.8(2) . . . . ?
N5 C3 N3 C1 -0.2(4) . . . . ?
N1 C1 N3 C3 -179.4(2) . . . . ?
N2 C1 N3 C3 1.5(4) . . . . ?
N4 C2 N5 C3 -178.5(3) . . . . ?
N2 C2 N5 C3 1.7(4) . . . . ?
N6 C3 N5 C2 179.6(3) . . . . ?
N3 C3 N5 C2 -1.4(4) . . . . ?

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 O2 0.86 2.06 2.887(3) 162.0 1_556 yes
N1 H1B O1 0.86 2.15 2.863(3) 140.2 2_676 yes
N4 H4A N2 0.86 2.15 3.009(3) 177.7 2_566 yes
N4 H4B O2 0.86 2.29 2.903(3) 128.7 2_565 yes
N4 H4B O3 0.86 2.34 3.049(3) 139.4 . yes
N6 H6A N3 0.86 2.16 3.019(3) 178.3 2_776 yes
N6 H6B N7 0.86 2.17 3.014(3) 167.7 1_655 yes
N5 H5 S1 0.84(3) 2.96(3) 3.669(3) 144(2) . yes
N5 H5 O3 0.84(3) 2.00(3) 2.780(3) 154(3) . yes
N7 H7A O3 0.878(17) 2.24(2) 3.061(3) 155(3) 2_565 yes
N7 H7B O1 0.883(17) 2.25(2) 3.086(3) 157(3) 2_575 yes

_shelx_res_file                  
;
TITL 1 in P-1
    1.res
    created by SHELXL-2018/3 at 18:05:23 on 19-May-2022
CELL 0.71073   5.14630   7.85200  10.51070  96.5174  96.6934  95.2649
ZERR    4.00   0.00200   0.00320   0.00370   0.0126   0.0117   0.0128
LATT  1
SFAC C H N O S
UNIT 6 18 14 6 2
TEMP 0
htab
EQIV $1 x, y, z+1
HTAB N1 O2_$1
EQIV $2 -x+1, -y+2, -z+1
HTAB N1 O1_$2
EQIV $3 -x, -y+1, -z+1
HTAB N4 N2_$3
EQIV $4 -x, -y+1, -z
HTAB N4 O2_$4
HTAB N4 O3
EQIV $5 -x+2, -y+2, -z+1
HTAB N6 N3_$5
EQIV $6 x+1, y, z
HTAB N6 N7_$6
HTAB N5 S1
HTAB N5 O3
HTAB N7 O3_$4
EQIV $7 -x, -y+2, -z
HTAB N7 O1_$7
L.S. 4
PLAN  5
TEMP 0
CONF
DFIX 0.9 N7 H7A N7 H7B
BOND
list 4
fmap 2
MORE -1
BOND $H
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>

WGHT    0.047800    0.123100
FVAR       0.29101
C1    1    0.514039    0.774957    0.589448    11.00000    0.02455    0.02746 =
         0.02320    0.00215    0.00258   -0.00029
C2    1    0.297529    0.626355    0.403405    11.00000    0.02593    0.02700 =
         0.02428    0.00205    0.00106   -0.00016
C3    1    0.680898    0.815662    0.403213    11.00000    0.02620    0.02678 =
         0.02451    0.00445    0.00131   -0.00219
S1    5    0.143254    0.756606    0.019109    11.00000    0.02672    0.03371 =
         0.02146   -0.00046    0.00269   -0.00829
O1    4    0.264961    0.925179    0.076256    11.00000    0.04190    0.03070 =
         0.04150   -0.00467   -0.00482   -0.01546
O2    4    0.138961    0.727424   -0.119274    11.00000    0.04084    0.06141 =
         0.01972    0.00132    0.00681   -0.01262
O3    4    0.255325    0.618515    0.081950    11.00000    0.03301    0.03427 =
         0.03207    0.00327   -0.00086   -0.00023
N1    3    0.530500    0.811590    0.715763    11.00000    0.03464    0.04907 =
         0.02201   -0.00389    0.00406   -0.01297
AFIX  93
H1A   2    0.415132    0.763521    0.757067    11.00000   -1.20000
H1B   2    0.656614    0.883575    0.756924    11.00000   -1.20000
AFIX   0
N2    3    0.310813    0.660765    0.531149    11.00000    0.02903    0.03021 =
         0.02376    0.00196    0.00245   -0.00523
N3    3    0.703297    0.853358    0.530516    11.00000    0.02755    0.03351 =
         0.02153    0.00117    0.00201   -0.00549
N4    3    0.107726    0.516512    0.337724    11.00000    0.03435    0.03986 =
         0.02373   -0.00215    0.00042   -0.01197
AFIX  93
H4A   2   -0.008892    0.466354    0.377234    11.00000   -1.20000
H4B   2    0.100156    0.494800    0.255238    11.00000   -1.20000
AFIX   0
N5    3    0.478221    0.704020    0.337842    11.00000    0.03156    0.03620 =
         0.01849    0.00052    0.00216   -0.00709
N6    3    0.851828    0.887069    0.335908    11.00000    0.03697    0.04435 =
         0.02280    0.00317    0.00497   -0.00909
AFIX  93
H6A   2    0.980320    0.959303    0.374445    11.00000   -1.20000
H6B   2    0.834995    0.861481    0.253404    11.00000   -1.20000
AFIX   0

H5    2    0.460713    0.685921    0.256973    11.00000    0.03476
N7    3   -0.160507    0.751267    0.055040    11.00000    0.02838    0.03287 =
         0.03138    0.00115    0.00416   -0.00135
H7A   2   -0.237878    0.648679    0.022471    11.00000   -1.20000
H7B   2   -0.236687    0.834757    0.020905    11.00000   -1.20000
HKLF 4




REM  1 in P-1
REM wR2 = 0.1173, GooF = S = 1.044, Restrained GooF = 1.044 for all data
REM R1 = 0.0522 for 1214 Fo > 4sig(Fo) and 0.1176 for all 1988 data
REM 137 parameters refined using 2 restraints

END

WGHT      0.0478      0.1231

REM Instructions for potential hydrogen bonds
HTAB N1 O2_$1
HTAB N1 O1_$2
HTAB N4 N2_$3
HTAB N4 O2_$4
HTAB N4 O3
HTAB N6 N3_$5
HTAB N6 N7_$6
HTAB N5 S1
HTAB N5 O3
HTAB N7 O3_$4
HTAB N7 O1_$7

REM Highest difference peak  0.297,  deepest hole -0.434,  1-sigma level  0.076
Q1    1   0.3209  0.6354  0.4737  11.00000  0.05    0.30
Q2    1   0.2896  0.6408  0.1826  11.00000  0.05    0.29
Q3    1   0.7053  1.0187  0.3657  11.00000  0.05    0.27
Q4    1   0.6204  0.9906  0.6029  11.00000  0.05    0.26
Q5    1   0.1859  0.5750 -0.0010  11.00000  0.05    0.26
;
_shelx_res_checksum              75714
