# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_GNPS
_database_code_depnum_ccdc_archive 'CCDC 2174343'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2022-02-18
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 O3 S, C H6 N3, 2(H2 O)'
_chemical_formula_sum            'C6 H13 N3 O5 S'
_chemical_formula_weight         239.25
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5403(12)
_cell_length_b                   8.1374(15)
_cell_length_c                   9.2100(11)
_cell_angle_alpha                92.107(12)
_cell_angle_beta                 94.692(12)
_cell_angle_gamma                112.190(16)
_cell_volume                     520.10(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1388
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.9260
_cell_measurement_theta_min      6.3440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.906
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3166
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.535
_diffrn_reflns_theta_min         4.831
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  51.00   1.00    1.00    --   40.73 -99.00 -60.00   50
  2  ω     32.00  68.00   1.00    1.00    --   40.73-125.00-120.00   36
  3  ω      5.00  33.00   1.00    1.00    --   40.73-104.00-133.00   28
  4  ω     44.00 127.00   1.00    1.20    --  107.58 -30.00-150.00   83
  5  ω     80.00 177.00   1.00    1.20    --  107.58  30.00-180.00   97
  6  ω     96.00 121.00   1.00    1.20    --  107.58 125.00-120.00   25
  7  ω    101.00 163.00   1.00    1.20    --  107.58  30.00  60.00   62
  8  ω     69.00 110.00   1.00    1.20    --  107.58 -95.00  60.00   41
  9  ω     51.00  95.00   1.00    1.20    --  107.58 -95.00 150.00   44
 10  ω     50.00 128.00   1.00    1.20    --  107.58 -45.00 120.00   78
 11  ω     52.00 127.00   1.00    1.20    --  107.58 -45.00   0.00   75
 12  ω     46.00  94.00   1.00    1.00    --   40.73-125.00  30.00   48
 13  ω     29.00  74.00   1.00    1.20    --  107.58 -95.00  30.00   45
 14  ω     46.00 114.00   1.00    1.20    --  107.58-125.00  30.00   68
 15  ω     69.00 132.00   1.00    1.20    --  107.58 -77.00-180.00   63
 16  ω   -114.00 -24.00   1.00    1.00    --  -40.73 -38.00 -30.00   90
 17  ω   -112.00 -19.00   1.00    1.00    --  -40.73 -38.00  60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0649820000
_diffrn_orient_matrix_UB_12      0.2014782000
_diffrn_orient_matrix_UB_13      -0.0161557000
_diffrn_orient_matrix_UB_21      -0.0305427000
_diffrn_orient_matrix_UB_22      0.0287852000
_diffrn_orient_matrix_UB_23      0.1608370000
_diffrn_orient_matrix_UB_31      0.2099043000
_diffrn_orient_matrix_UB_32      0.0246409000
_diffrn_orient_matrix_UB_33      0.0468001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1669
_reflns_number_total             1998
_reflns_odcompleteness_completeness 99.30
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0789
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1298P)²+1.5729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2557
_refine_ls_wR_factor_ref         0.2675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_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 0.39455(17) 0.68300(16) 0.75201(12) 0.0165(4) Uani 1 1 d . . . . .
C1 C 0.4618(8) 1.0344(7) 0.7694(6) 0.0204(11) Uani 1 1 d . . . . .
H1 H 0.440252 1.017885 0.866776 0.024 Uiso 1 1 calc R U . . .
C2 C 0.4527(7) 0.8935(7) 0.6774(5) 0.0165(10) Uani 1 1 d . . . . .
C3 C 0.4796(7) 0.9131(7) 0.5263(6) 0.0183(11) Uani 1 1 d . . . . .
C4 C 0.4683(7) 0.7712(7) 0.4273(6) 0.0194(11) Uani 1 1 d . . . . .
H4 H 0.441449 0.658747 0.460774 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4960(7) 0.7961(7) 0.2844(6) 0.0182(10) Uani 1 1 d . . . . .
H5 H 0.487126 0.700616 0.221497 0.022 Uiso 1 1 calc R U . . .
C6 C 0.9369(8) 0.7344(7) 0.9887(6) 0.0214(11) Uani 1 1 d . . . . .
N1 N 1.1073(7) 0.7733(7) 1.0617(5) 0.0243(10) Uani 1 1 d . . . . .
H1A H 1.135666 0.834020 1.144708 0.029 Uiso 1 1 calc R U . . .
H1B H 1.189980 0.737875 1.026432 0.029 Uiso 1 1 calc R U . . .
N2 N 0.8098(7) 0.7895(7) 1.0439(5) 0.0242(10) Uani 1 1 d . . . . .
H2A H 0.838738 0.850205 1.126883 0.029 Uiso 1 1 calc R U . . .
H2B H 0.698496 0.764405 0.996591 0.029 Uiso 1 1 calc R U . . .
N3 N 0.8941(7) 0.6409(6) 0.8602(5) 0.0241(10) Uani 1 1 d . . . . .
H3A H 0.977351 0.606127 0.825035 0.029 Uiso 1 1 calc R U . . .
H3B H 0.783144 0.615297 0.812185 0.029 Uiso 1 1 calc R U . . .
O1 O 0.4078(5) 0.7168(5) 0.9102(4) 0.0215(8) Uani 1 1 d . . . . .
O2 O 0.5313(5) 0.6092(5) 0.7091(4) 0.0199(8) Uani 1 1 d . . . . .
O3 O 0.1956(5) 0.5766(5) 0.6902(4) 0.0214(8) Uani 1 1 d . . . . .
O1W O 0.0452(6) 0.2794(5) 0.4820(4) 0.0272(9) Uani 1 1 d G . . . .
H1WA H 0.109097 0.364141 0.545499 0.041 Uiso 1 1 d G U . . .
H1WB H -0.041910 0.310636 0.442344 0.041 Uiso 1 1 d G U . . .
O2W O -0.0505(6) 0.0262(6) 0.6909(4) 0.0288(9) Uani 1 1 d G . . . .
H2WA H -0.032612 0.091095 0.618973 0.043 Uiso 1 1 d G U . . .
H2WB H -0.079382 -0.078515 0.652620 0.043 Uiso 1 1 d G 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 C2 1.779(5) . ?
S1 O1 1.461(4) . ?
S1 O2 1.448(4) . ?
S1 O3 1.472(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(7) . ?
C1 C5 1.412(7) 2_676 ?
C2 C3 1.429(7) . ?
C3 C3 1.440(10) 2_676 ?
C3 C4 1.417(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.360(7) . ?
C5 H5 0.9300 . ?
C6 N1 1.318(7) . ?
C6 N2 1.329(7) . ?
C6 N3 1.330(7) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8502 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?

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 C2 106.3(2) . . ?
O1 S1 O3 111.6(2) . . ?
O2 S1 C2 107.9(2) . . ?
O2 S1 O1 112.4(2) . . ?
O2 S1 O3 112.9(2) . . ?
O3 S1 C2 105.2(2) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C5 119.9(5) . 2_676 ?
C5 C1 H1 120.1 2_676 . ?
C1 C2 S1 117.4(4) . . ?
C1 C2 C3 121.4(5) . . ?
C3 C2 S1 121.1(4) . . ?
C2 C3 C3 117.6(6) . 2_676 ?
C4 C3 C2 123.3(5) . . ?
C4 C3 C3 119.0(6) . 2_676 ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(5) . . ?
C5 C4 H4 119.3 . . ?
C1 C5 H5 119.7 2_676 . ?
C4 C5 C1 120.6(5) . 2_676 ?
C4 C5 H5 119.7 . . ?
N1 C6 N2 119.7(5) . . ?
N1 C6 N3 119.7(5) . . ?
N2 C6 N3 120.6(5) . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C6 N3 H3A 120.0 . . ?
C6 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?

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
S1 C2 C3 C3 178.1(5) . . . 2_676 ?
S1 C2 C3 C4 -2.0(7) . . . . ?
C1 C2 C3 C3 1.2(9) . . . 2_676 ?
C1 C2 C3 C4 -178.9(5) . . . . ?
C2 C3 C4 C5 -179.6(5) . . . . ?
C3 C3 C4 C5 0.3(9) 2_676 . . . ?
C3 C4 C5 C1 0.4(8) . . . 2_676 ?
C5 C1 C2 S1 -178.9(4) 2_676 . . . ?
C5 C1 C2 C3 -1.8(8) 2_676 . . . ?
O1 S1 C2 C1 -11.6(5) . . . . ?
O1 S1 C2 C3 171.3(4) . . . . ?
O2 S1 C2 C1 -132.4(4) . . . . ?
O2 S1 C2 C3 50.6(5) . . . . ?
O3 S1 C2 C1 106.9(4) . . . . ?
O3 S1 C2 C3 -70.2(4) . . . . ?

_olex2_date_sample_data_collection 2020-10-08
_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 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.397
####################################################################### 
# 
# 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_GNPS-1
_database_code_depnum_ccdc_archive 'CCDC 2174344'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 O6 S2, C10 H18 O, 2(C H6 N3), H2 O'
_chemical_formula_sum            'C22 H38 N6 O8 S2'
_chemical_formula_weight         578.70
_chemical_absolute_configuration unknown
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6827(2)
_cell_length_b                   16.9136(6)
_cell_length_c                   21.7131(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2821.45(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4544
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5680
_cell_measurement_theta_min      4.0470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7301
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.823
_diffrn_reflns_theta_min         3.312
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  60.00   1.00    1.00    --   40.73 -99.00 -90.00   38
  2  ω     36.00 118.00   1.00    1.52    --  107.58 -45.00   0.00   82
  3  ω     69.00 102.00   1.00    1.52    --  107.58 -94.00-120.00   33
  4  ω     25.00  66.00   1.00    1.52    --  107.58 -94.00-120.00   41
  5  ω    141.00 171.00   1.00    1.52    --  107.58  45.00 -90.00   30
  6  ω     97.00 178.00   1.00    1.52    --  107.58 125.00  90.00   81
  7  ω   -112.00  23.00   1.00    1.00    --  -40.73   0.00-150.00  135
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0393849000
_diffrn_orient_matrix_UB_12      0.0517626000
_diffrn_orient_matrix_UB_13      0.0567854000
_diffrn_orient_matrix_UB_21      0.0505217000
_diffrn_orient_matrix_UB_22      0.0691292000
_diffrn_orient_matrix_UB_23      -0.0426873000
_diffrn_orient_matrix_UB_31      -0.1897263000
_diffrn_orient_matrix_UB_32      0.0289833000
_diffrn_orient_matrix_UB_33      0.0004857000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_full    0.741
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                4486
_reflns_number_total             4859
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.056
_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)+(0.0399P)²+0.7691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1022
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19)
2.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3C,H3D), N4(H4A,H4B), N5(H5C,H5D), N6(H6C,H6D)
2.f Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.g Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.28824(12) 0.72776(5) 0.60134(4) 0.02213(19) Uani 1 1 d . . . . .
S2 S -0.15182(12) 0.67874(6) 0.87511(4) 0.02246(19) Uani 1 1 d . . . . .
O1 O 0.3813(3) 0.80064(15) 0.61541(11) 0.0261(6) Uani 1 1 d . . . . .
O2 O 0.2116(4) 0.72838(16) 0.53975(10) 0.0276(6) Uani 1 1 d . . . . .
O3 O 0.3950(4) 0.65767(16) 0.61228(11) 0.0264(6) Uani 1 1 d . . . . .
O4 O -0.2574(3) 0.75068(15) 0.87283(11) 0.0260(6) Uani 1 1 d . . . . .
O5 O -0.2515(3) 0.60916(16) 0.85709(11) 0.0269(6) Uani 1 1 d . . . . .
O6 O -0.0691(4) 0.66875(16) 0.93552(10) 0.0272(6) Uani 1 1 d . . . . .
O7 O 0.3483(4) 0.49647(16) 0.60590(11) 0.0300(6) Uani 1 1 d . . . . .
H7 H 0.353319 0.544584 0.610173 0.045 Uiso 1 1 calc R U . . .
C1 C 0.5669(5) 0.4834(2) 0.68716(17) 0.0274(9) Uani 1 1 d . . . . .
H1 H 0.564136 0.540778 0.693255 0.033 Uiso 1 1 calc R U . . .
C2 C 0.3884(5) 0.4585(2) 0.66374(16) 0.0278(8) Uani 1 1 d . . . . .
H2 H 0.391568 0.401279 0.656494 0.033 Uiso 1 1 calc R U . . .
C3 C 0.2451(5) 0.4749(3) 0.71040(17) 0.0304(9) Uani 1 1 d . . . . .
H3A H 0.135045 0.455656 0.694450 0.036 Uiso 1 1 calc R U . . .
H3B H 0.234809 0.531469 0.716618 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2835(6) 0.4347(3) 0.77207(17) 0.0346(9) Uani 1 1 d . . . . .
H4 H 0.290723 0.377687 0.764625 0.041 Uiso 1 1 calc R U . . .
C5 C 0.4581(6) 0.4617(3) 0.79614(18) 0.0375(10) Uani 1 1 d . . . . .
H5A H 0.482849 0.434658 0.834575 0.045 Uiso 1 1 calc R U . . .
H5B H 0.453760 0.517954 0.804495 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6034(6) 0.4449(3) 0.75046(19) 0.0396(11) Uani 1 1 d . . . . .
H6A H 0.615646 0.388236 0.745287 0.048 Uiso 1 1 calc R U . . .
H6B H 0.712273 0.465216 0.766671 0.048 Uiso 1 1 calc R U . . .
C7 C 0.7097(6) 0.4657(3) 0.6413(2) 0.0366(10) Uani 1 1 d . . . . .
C8 C 0.8138(7) 0.5220(3) 0.6205(2) 0.0482(12) Uani 1 1 d . . . . .
H8A H 0.799(7) 0.577(3) 0.636(2) 0.048(15) Uiso 1 1 d . . . . .
H8B H 0.903(8) 0.506(3) 0.589(3) 0.063(17) Uiso 1 1 d . . . . .
C9 C 0.7291(9) 0.3819(3) 0.6201(3) 0.074(2) Uani 1 1 d . . . . .
H9A H 0.764839 0.349448 0.654116 0.111 Uiso 1 1 calc R U . . .
H9B H 0.815310 0.379349 0.588151 0.111 Uiso 1 1 calc R U . . .
H9C H 0.619763 0.363169 0.604481 0.111 Uiso 1 1 calc R U . . .
C10 C 0.1372(7) 0.4488(3) 0.8185(2) 0.0494(13) Uani 1 1 d . . . . .
H10A H 0.127602 0.504331 0.826807 0.074 Uiso 1 1 calc R U . . .
H10B H 0.162788 0.421063 0.855972 0.074 Uiso 1 1 calc R U . . .
H10C H 0.029422 0.429720 0.801745 0.074 Uiso 1 1 calc R U . . .
C11 C 0.1095(5) 0.7231(2) 0.65368(15) 0.0224(7) Uani 1 1 d . . . . .
C12 C -0.0542(5) 0.7327(3) 0.63108(16) 0.0278(8) Uani 1 1 d . . . . .
H12 H -0.070628 0.741548 0.589209 0.033 Uiso 1 1 calc R U . . .
C13 C -0.1990(5) 0.7293(3) 0.67070(17) 0.0300(8) Uani 1 1 d . . . . .
H13 H -0.310407 0.737265 0.655105 0.036 Uiso 1 1 calc R U . . .
C14 C -0.1764(5) 0.7142(2) 0.73215(16) 0.0262(8) Uani 1 1 d . . . . .
H14 H -0.273386 0.710335 0.757591 0.031 Uiso 1 1 calc R U . . .
C15 C -0.0087(5) 0.7044(2) 0.75768(16) 0.0217(7) Uani 1 1 d . . . . .
C16 C 0.1403(5) 0.7109(2) 0.71817(15) 0.0213(7) Uani 1 1 d . . . . .
C17 C 0.3087(5) 0.7041(2) 0.74387(16) 0.0255(8) Uani 1 1 d . . . . .
H17 H 0.405373 0.709606 0.718449 0.031 Uiso 1 1 calc R U . . .
C18 C 0.3329(5) 0.6895(3) 0.80552(16) 0.0290(9) Uani 1 1 d . . . . .
H18 H 0.444708 0.684599 0.821458 0.035 Uiso 1 1 calc R U . . .
C19 C 0.1867(5) 0.6821(2) 0.84449(15) 0.0268(8) Uani 1 1 d . . . . .
H19 H 0.202872 0.671851 0.886188 0.032 Uiso 1 1 calc R U . . .
C20 C 0.0221(5) 0.6896(2) 0.82170(16) 0.0217(7) Uani 1 1 d . . . . .
C21 C 0.1150(5) 0.9486(2) 0.53136(16) 0.0268(8) Uani 1 1 d . . . . .
N1 N 0.0417(5) 1.0137(2) 0.51011(15) 0.0366(9) Uani 1 1 d . . . . .
H1A H -0.011091 1.013126 0.475186 0.044 Uiso 1 1 calc R U . . .
H1B H 0.046686 1.056689 0.531193 0.044 Uiso 1 1 calc R U . . .
N2 N 0.1982(4) 0.9498(2) 0.58511(13) 0.0269(7) Uani 1 1 d . . . . .
H2A H 0.204213 0.992977 0.605949 0.032 Uiso 1 1 calc R U . . .
H2B H 0.246036 0.907446 0.598997 0.032 Uiso 1 1 calc R U . . .
N3 N 0.1076(5) 0.8825(2) 0.49916(15) 0.0362(9) Uani 1 1 d . . . . .
H3C H 0.054966 0.881686 0.464215 0.043 Uiso 1 1 calc R U . . .
H3D H 0.155535 0.840148 0.513134 0.043 Uiso 1 1 calc R U . . .
N4 N 0.0367(5) 0.4271(2) 0.45313(15) 0.0315(8) Uani 1 1 d . . . . .
H4A H 0.074062 0.473655 0.461888 0.038 Uiso 1 1 calc R U . . .
H4B H -0.024954 0.419606 0.420581 0.038 Uiso 1 1 calc R U . . .
N5 N 0.1686(5) 0.3775(2) 0.53999(14) 0.0306(7) Uani 1 1 d . . . . .
H5C H 0.206491 0.423944 0.549055 0.037 Uiso 1 1 calc R U . . .
H5D H 0.192273 0.338107 0.563552 0.037 Uiso 1 1 calc R U . . .
N6 N 0.0201(5) 0.29440(19) 0.47544(15) 0.0307(8) Uani 1 1 d . . . . .
H6C H 0.046905 0.255086 0.498709 0.037 Uiso 1 1 calc R U . . .
H6D H -0.041462 0.286873 0.442892 0.037 Uiso 1 1 calc R U . . .
O1W O 0.1046(5) 0.59483(19) 0.46846(16) 0.0513(10) Uani 1 1 d G . . . .
H1WA H 0.139990 0.626178 0.496381 0.077 Uiso 1 1 d G U . . .
H1WB H 0.044096 0.620307 0.442389 0.077 Uiso 1 1 d G U . . .
C22 C 0.0740(5) 0.3668(2) 0.48979(16) 0.0254(8) Uani 1 1 d . . . . .


_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 1.457(3) . ?
S1 O2 1.461(2) . ?
S1 O3 1.461(3) . ?
S1 C11 1.784(4) . ?
S2 O4 1.463(3) . ?
S2 O5 1.457(3) . ?
S2 O6 1.467(3) . ?
S2 C20 1.779(4) . ?
O7 H7 0.8200 . ?
O7 C2 1.444(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.522(6) . ?
C1 C6 1.546(5) . ?
C1 C7 1.511(6) . ?
C2 H2 0.9800 . ?
C2 C3 1.522(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.530(5) . ?
C4 H4 0.9800 . ?
C4 C5 1.510(6) . ?
C4 C10 1.527(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.520(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.323(7) . ?
C7 C9 1.498(7) . ?
C8 H8A 1.00(5) . ?
C8 H8B 1.00(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.360(5) . ?
C11 C16 1.435(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.407(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.412(5) . ?
C15 C16 1.435(5) . ?
C15 C20 1.432(5) . ?
C16 C17 1.414(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.412(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.365(5) . ?
C21 N1 1.320(5) . ?
C21 N2 1.331(5) . ?
C21 N3 1.321(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3C 0.8600 . ?
N3 H3D 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C22 1.325(5) . ?
N5 H5C 0.8600 . ?
N5 H5D 0.8600 . ?
N5 C22 1.323(5) . ?
N6 H6C 0.8600 . ?
N6 H6D 0.8600 . ?
N6 C22 1.330(5) . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8501 . ?

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 112.55(15) . . ?
O1 S1 O3 112.13(16) . . ?
O1 S1 C11 106.33(17) . . ?
O2 S1 C11 105.86(17) . . ?
O3 S1 O2 112.39(16) . . ?
O3 S1 C11 107.02(17) . . ?
O4 S2 O6 111.49(16) . . ?
O4 S2 C20 107.94(17) . . ?
O5 S2 O4 111.79(16) . . ?
O5 S2 O6 111.99(16) . . ?
O5 S2 C20 107.65(16) . . ?
O6 S2 C20 105.62(17) . . ?
C2 O7 H7 109.5 . . ?
C2 C1 H1 107.5 . . ?
C2 C1 C6 110.1(3) . . ?
C6 C1 H1 107.5 . . ?
C7 C1 H1 107.5 . . ?
C7 C1 C2 112.3(3) . . ?
C7 C1 C6 111.8(3) . . ?
O7 C2 C1 111.1(3) . . ?
O7 C2 H2 107.7 . . ?
O7 C2 C3 110.1(3) . . ?
C1 C2 H2 107.8 . . ?
C1 C2 C3 112.3(3) . . ?
C3 C2 H2 107.7 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.2(3) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4 107.7 . . ?
C5 C4 C3 109.9(4) . . ?
C5 C4 H4 107.7 . . ?
C5 C4 C10 112.2(4) . . ?
C10 C4 C3 111.5(4) . . ?
C10 C4 H4 107.7 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.8(4) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C1 C6 H6A 109.3 . . ?
C1 C6 H6B 109.3 . . ?
C5 C6 C1 111.6(4) . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C1 121.4(4) . . ?
C8 C7 C9 121.1(5) . . ?
C9 C7 C1 117.5(4) . . ?
C7 C8 H8A 119(3) . . ?
C7 C8 H8B 117(3) . . ?
H8A C8 H8B 124(5) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 S1 118.5(3) . . ?
C12 C11 C16 121.4(3) . . ?
C16 C11 S1 120.1(3) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 119.0(3) . . ?
C14 C15 C20 123.5(3) . . ?
C20 C15 C16 117.5(3) . . ?
C15 C16 C11 117.6(3) . . ?
C17 C16 C11 123.2(3) . . ?
C17 C16 C15 119.2(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.5(3) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.5(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 S2 121.8(3) . . ?
C19 C20 S2 116.7(3) . . ?
C19 C20 C15 121.4(3) . . ?
N1 C21 N2 119.9(4) . . ?
N1 C21 N3 120.2(3) . . ?
N3 C21 N2 119.8(4) . . ?
C21 N1 H1A 120.0 . . ?
C21 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C21 N2 H2A 120.0 . . ?
C21 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C21 N3 H3C 120.0 . . ?
C21 N3 H3D 120.0 . . ?
H3C N3 H3D 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C22 N4 H4A 120.0 . . ?
C22 N4 H4B 120.0 . . ?
H5C N5 H5D 120.0 . . ?
C22 N5 H5C 120.0 . . ?
C22 N5 H5D 120.0 . . ?
H6C N6 H6D 120.0 . . ?
C22 N6 H6C 120.0 . . ?
C22 N6 H6D 120.0 . . ?
H1WA O1W H1WB 109.5 . . ?
N4 C22 N6 120.0(3) . . ?
N5 C22 N4 120.6(4) . . ?
N5 C22 N6 119.4(4) . . ?

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
S1 C11 C12 C13 179.8(3) . . . . ?
S1 C11 C16 C15 -177.5(3) . . . . ?
S1 C11 C16 C17 1.7(5) . . . . ?
O1 S1 C11 C12 110.4(3) . . . . ?
O1 S1 C11 C16 -68.5(3) . . . . ?
O2 S1 C11 C12 -9.5(4) . . . . ?
O2 S1 C11 C16 171.6(3) . . . . ?
O3 S1 C11 C12 -129.5(3) . . . . ?
O3 S1 C11 C16 51.5(4) . . . . ?
O4 S2 C20 C15 -57.7(3) . . . . ?
O4 S2 C20 C19 123.3(3) . . . . ?
O5 S2 C20 C15 63.1(3) . . . . ?
O5 S2 C20 C19 -115.9(3) . . . . ?
O6 S2 C20 C15 -177.1(3) . . . . ?
O6 S2 C20 C19 3.9(4) . . . . ?
O7 C2 C3 C4 179.6(3) . . . . ?
C1 C2 C3 C4 -56.2(5) . . . . ?
C2 C1 C6 C5 -53.5(5) . . . . ?
C2 C1 C7 C8 123.2(5) . . . . ?
C2 C1 C7 C9 -56.8(6) . . . . ?
C2 C3 C4 C5 56.7(5) . . . . ?
C2 C3 C4 C10 -178.1(4) . . . . ?
C3 C4 C5 C6 -57.2(5) . . . . ?
C4 C5 C6 C1 56.3(5) . . . . ?
C6 C1 C2 O7 177.5(3) . . . . ?
C6 C1 C2 C3 53.7(5) . . . . ?
C6 C1 C7 C8 -112.5(5) . . . . ?
C6 C1 C7 C9 67.6(6) . . . . ?
C7 C1 C2 O7 -57.3(4) . . . . ?
C7 C1 C2 C3 179.0(3) . . . . ?
C7 C1 C6 C5 -179.0(4) . . . . ?
C10 C4 C5 C6 178.1(4) . . . . ?
C11 C12 C13 C14 -1.7(7) . . . . ?
C11 C16 C17 C18 -177.6(4) . . . . ?
C12 C11 C16 C15 3.6(6) . . . . ?
C12 C11 C16 C17 -177.2(4) . . . . ?
C12 C13 C14 C15 2.2(7) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C13 C14 C15 C20 179.1(4) . . . . ?
C14 C15 C16 C11 -3.1(5) . . . . ?
C14 C15 C16 C17 177.7(4) . . . . ?
C14 C15 C20 S2 2.2(6) . . . . ?
C14 C15 C20 C19 -178.8(4) . . . . ?
C15 C16 C17 C18 1.6(6) . . . . ?
C16 C11 C12 C13 -1.3(7) . . . . ?
C16 C15 C20 S2 -178.9(3) . . . . ?
C16 C15 C20 C19 0.1(6) . . . . ?
C16 C17 C18 C19 -0.8(6) . . . . ?
C17 C18 C19 C20 -0.4(6) . . . . ?
C18 C19 C20 S2 179.8(3) . . . . ?
C18 C19 C20 C15 0.8(6) . . . . ?
C20 C15 C16 C11 178.0(4) . . . . ?
C20 C15 C16 C17 -1.2(5) . . . . ?

_olex2_date_sample_data_collection 2020-10-28
_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.456
####################################################################### 
# 
# 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_GNPS-8
_database_code_depnum_ccdc_archive 'CCDC 2174347'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 O6 S2, C10 H14 O, 2(C H6 N3)'
_chemical_formula_sum            'C22 H32 N6 O7 S2'
_chemical_formula_weight         556.65
_chemical_absolute_configuration unknown
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.32784(12)
_cell_length_b                   14.8045(2)
_cell_length_c                   21.3026(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2626.38(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5404
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7880
_cell_measurement_theta_min      2.0870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.300
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6665
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.879
_diffrn_reflns_theta_min         3.636
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  44.00   1.00    1.00    --   40.73 -38.00   0.00   74
  2  ω     50.00  77.00   1.00    1.00    --   40.73 -99.00 120.00   27
  3  ω     25.00  97.00   1.00    1.00    --  107.58 -94.00 -60.00   72
  4  ω     98.00 173.00   1.00    1.00    --  107.58  45.00  30.00   75
  5  ω     95.00 178.00   1.00    1.00    --  107.58 125.00 -90.00   83
  6  ω     94.00 131.00   1.00    1.00    --  107.58 125.00 -30.00   37
  7  ω    -46.00  16.00   1.00    1.00    --  -40.73  38.00-150.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0428403000
_diffrn_orient_matrix_UB_12      0.0332256000
_diffrn_orient_matrix_UB_13      -0.0664541000
_diffrn_orient_matrix_UB_21      -0.0180545000
_diffrn_orient_matrix_UB_22      0.0986282000
_diffrn_orient_matrix_UB_23      0.0220654000
_diffrn_orient_matrix_UB_31      0.1789555000
_diffrn_orient_matrix_UB_32      0.0020419000
_diffrn_orient_matrix_UB_33      0.0181359000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.503
_reflns_Friedel_fraction_full    0.699
_reflns_Friedel_fraction_max     0.644
_reflns_number_gt                4328
_reflns_number_total             4421
_reflns_odcompleteness_completeness 99.96
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.034
_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)+(0.0837P)²+0.1411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2C,H2D), N3(H3A,H3B), N4(H4C,H4D), N5(H5A,H5B), N6(H6A,H6B)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.30420(9) 0.37979(5) 0.11206(3) 0.01353(18) Uani 1 1 d . . . . .
S2 S 0.64704(8) 0.38414(5) 0.40509(3) 0.01320(18) Uani 1 1 d . . . . .
O1 O 0.3883(3) 0.37509(15) 0.05222(9) 0.0181(5) Uani 1 1 d . . . . .
O2 O 0.2060(3) 0.46143(13) 0.11735(10) 0.0173(5) Uani 1 1 d . . . . .
O3 O 0.2115(3) 0.29818(14) 0.12541(10) 0.0178(5) Uani 1 1 d . . . . .
O4 O 0.7455(3) 0.46491(13) 0.39744(10) 0.0179(5) Uani 1 1 d . . . . .
O5 O 0.7408(3) 0.30206(13) 0.39419(10) 0.0165(5) Uani 1 1 d . . . . .
O6 O 0.5634(3) 0.38202(15) 0.46502(9) 0.0172(4) Uani 1 1 d . . . . .
O7 O 0.5185(3) -0.10669(15) 0.60024(9) 0.0207(5) Uani 1 1 d . . . . .
C1 C 0.5547(4) -0.1148(2) 0.65609(13) 0.0155(6) Uani 1 1 d . . . . .
C2 C 0.4346(4) -0.0960(2) 0.70717(14) 0.0181(6) Uani 1 1 d . . . . .
H2A H 0.327093 -0.103914 0.690546 0.022 Uiso 1 1 calc R U . . .
H2B H 0.445292 -0.033695 0.720570 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4568(4) -0.1582(2) 0.76407(14) 0.0163(6) Uani 1 1 d . . . . .
H3 H 0.442756 -0.220302 0.749104 0.020 Uiso 1 1 calc R U . . .
C4 C 0.6291(4) -0.1501(2) 0.78729(15) 0.0217(7) Uani 1 1 d . . . . .
H4A H 0.641898 -0.092903 0.808874 0.026 Uiso 1 1 calc R U . . .
H4B H 0.650033 -0.197997 0.817287 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7493(4) -0.1558(2) 0.73534(17) 0.0248(7) Uani 1 1 d . . . . .
H5 H 0.854025 -0.171263 0.746048 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7181(4) -0.1403(2) 0.67446(16) 0.0197(7) Uani 1 1 d . . . . .
C7 C 0.8444(4) -0.1464(2) 0.62415(17) 0.0280(8) Uani 1 1 d . . . . .
H7A H 0.819265 -0.195348 0.596276 0.042 Uiso 1 1 calc R U . . .
H7B H 0.947246 -0.156860 0.643148 0.042 Uiso 1 1 calc R U . . .
H7C H 0.847233 -0.090846 0.600932 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3303(4) -0.1424(2) 0.81466(15) 0.0202(7) Uani 1 1 d . . . . .
C9 C 0.3658(5) -0.1281(3) 0.87456(16) 0.0287(8) Uani 1 1 d . . . . .
H9A H 0.271(5) -0.122(3) 0.9067(19) 0.033(11) Uiso 1 1 d . . . . .
H9B H 0.485(4) -0.127(2) 0.8864(15) 0.014(8) Uiso 1 1 d . . . . .
C10 C 0.1590(4) -0.1462(2) 0.79282(16) 0.0232(7) Uani 1 1 d . . . . .
H10A H 0.134779 -0.093102 0.768791 0.035 Uiso 1 1 calc R U . . .
H10B H 0.088930 -0.149272 0.828545 0.035 Uiso 1 1 calc R U . . .
H10C H 0.143709 -0.198848 0.767145 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4550(4) 0.3876(2) 0.17094(13) 0.0138(6) Uani 1 1 d . . . . .
C12 C 0.6120(4) 0.3894(2) 0.15207(13) 0.0168(6) Uani 1 1 d . . . . .
H12 H 0.636891 0.389430 0.109511 0.020 Uiso 1 1 calc R U . . .
C13 C 0.7358(4) 0.3913(2) 0.19691(15) 0.0192(6) Uani 1 1 d . . . . .
H13 H 0.842317 0.393326 0.183906 0.023 Uiso 1 1 calc R U . . .
C14 C 0.7001(4) 0.3902(2) 0.25969(13) 0.0164(6) Uani 1 1 d . . . . .
H14 H 0.783126 0.390193 0.288902 0.020 Uiso 1 1 calc R U . . .
C15 C 0.5392(4) 0.3889(2) 0.28075(13) 0.0135(6) Uani 1 1 d . . . . .
C16 C 0.4109(4) 0.3892(2) 0.23605(13) 0.0136(6) Uani 1 1 d . . . . .
C17 C 0.2504(4) 0.3898(2) 0.25705(13) 0.0153(6) Uani 1 1 d . . . . .
H17 H 0.167209 0.391043 0.227931 0.018 Uiso 1 1 calc R U . . .
C18 C 0.2155(4) 0.3885(2) 0.32010(14) 0.0184(6) Uani 1 1 d . . . . .
H18 H 0.108978 0.389185 0.333181 0.022 Uiso 1 1 calc R U . . .
C19 C 0.3389(4) 0.3862(2) 0.36502(13) 0.0167(6) Uani 1 1 d . . . . .
H19 H 0.314036 0.384021 0.407556 0.020 Uiso 1 1 calc R U . . .
C20 C 0.4954(4) 0.3873(2) 0.34605(13) 0.0143(6) Uani 1 1 d . . . . .
C21 C 0.5650(4) 0.1213(2) 0.48956(13) 0.0156(6) Uani 1 1 d . . . . .
C22 C 0.6053(3) 0.6404(2) 0.50511(14) 0.0140(6) Uani 1 1 d . . . . .
N1 N 0.6981(3) 0.64352(17) 0.45508(12) 0.0181(5) Uani 1 1 d . . . . .
H1A H 0.725492 0.694821 0.439461 0.022 Uiso 1 1 calc R U . . .
H1B H 0.731243 0.594279 0.438023 0.022 Uiso 1 1 calc R U . . .
N2 N 0.5541(3) 0.71607(17) 0.53147(12) 0.0197(6) Uani 1 1 d . . . . .
H2C H 0.581367 0.767435 0.515919 0.024 Uiso 1 1 calc R U . . .
H2D H 0.493529 0.713872 0.564133 0.024 Uiso 1 1 calc R U . . .
N3 N 0.5678(3) 0.56035(17) 0.53008(12) 0.0183(6) Uani 1 1 d . . . . .
H3A H 0.604152 0.511497 0.513487 0.022 Uiso 1 1 calc R U . . .
H3B H 0.507319 0.557685 0.562741 0.022 Uiso 1 1 calc R U . . .
N4 N 0.5104(4) 0.19686(17) 0.51457(13) 0.0219(6) Uani 1 1 d . . . . .
H4C H 0.449392 0.194872 0.547131 0.026 Uiso 1 1 calc R U . . .
H4D H 0.535728 0.248072 0.498312 0.026 Uiso 1 1 calc R U . . .
N5 N 0.6613(3) 0.12467(18) 0.43978(12) 0.0218(6) Uani 1 1 d . . . . .
H5A H 0.698265 0.075568 0.423780 0.026 Uiso 1 1 calc R U . . .
H5B H 0.686465 0.175964 0.423606 0.026 Uiso 1 1 calc R U . . .
N6 N 0.5267(4) 0.04234(17) 0.51419(12) 0.0203(6) Uani 1 1 d . . . . .
H6A H 0.465788 0.039920 0.546746 0.024 Uiso 1 1 calc R U . . .
H6B H 0.562673 -0.006658 0.497684 0.024 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 1.456(2) . ?
S1 O2 1.464(2) . ?
S1 O3 1.462(2) . ?
S1 C11 1.778(3) . ?
S2 O4 1.459(2) . ?
S2 O5 1.463(2) . ?
S2 O6 1.455(2) . ?
S2 C20 1.783(3) . ?
O7 C1 1.233(4) . ?
C1 C2 1.504(4) . ?
C1 C6 1.465(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.533(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.522(4) . ?
C3 C8 1.525(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.495(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.343(5) . ?
C6 C7 1.504(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.327(4) . ?
C8 C10 1.501(5) . ?
C9 H9A 1.05(4) . ?
C9 H9B 1.02(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.369(4) . ?
C11 C16 1.435(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.405(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.413(4) . ?
C15 C16 1.431(4) . ?
C15 C20 1.438(4) . ?
C16 C17 1.410(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.404(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(4) . ?
C21 N4 1.320(4) . ?
C21 N5 1.330(4) . ?
C21 N6 1.320(4) . ?
C22 N1 1.317(4) . ?
C22 N2 1.324(4) . ?
C22 N3 1.335(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2C 0.8600 . ?
N2 H2D 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4C 0.8600 . ?
N4 H4D 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 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
O1 S1 O2 112.06(13) . . ?
O1 S1 O3 112.63(13) . . ?
O1 S1 C11 106.32(13) . . ?
O2 S1 C11 106.64(13) . . ?
O3 S1 O2 111.87(12) . . ?
O3 S1 C11 106.83(13) . . ?
O4 S2 O5 111.29(12) . . ?
O4 S2 C20 107.33(13) . . ?
O5 S2 C20 106.73(13) . . ?
O6 S2 O4 112.63(13) . . ?
O6 S2 O5 112.15(13) . . ?
O6 S2 C20 106.28(14) . . ?
O7 C1 C2 121.2(3) . . ?
O7 C1 C6 120.7(3) . . ?
C6 C1 C2 118.2(3) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.4(3) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3 107.0 . . ?
C4 C3 C2 108.9(3) . . ?
C4 C3 H3 107.0 . . ?
C4 C3 C8 114.2(3) . . ?
C8 C3 C2 112.5(3) . . ?
C8 C3 H3 107.0 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.7(3) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5 117.4 . . ?
C6 C5 C4 125.2(3) . . ?
C6 C5 H5 117.4 . . ?
C1 C6 C7 118.3(3) . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 122.9(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C3 123.3(3) . . ?
C9 C8 C10 121.1(3) . . ?
C10 C8 C3 115.6(3) . . ?
C8 C9 H9A 118(2) . . ?
C8 C9 H9B 117.1(19) . . ?
H9A C9 H9B 125(3) . . ?
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 . . ?
C12 C11 S1 118.0(2) . . ?
C12 C11 C16 121.9(3) . . ?
C16 C11 S1 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 C20 123.2(3) . . ?
C16 C15 C20 117.0(3) . . ?
C15 C16 C11 116.9(3) . . ?
C17 C16 C11 123.3(3) . . ?
C17 C16 C15 119.8(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 S2 120.2(2) . . ?
C19 C20 S2 117.9(2) . . ?
C19 C20 C15 121.9(3) . . ?
N4 C21 N5 119.8(3) . . ?
N6 C21 N4 120.4(3) . . ?
N6 C21 N5 119.7(3) . . ?
N1 C22 N2 120.1(3) . . ?
N1 C22 N3 119.4(3) . . ?
N2 C22 N3 120.4(3) . . ?
C22 N1 H1A 120.0 . . ?
C22 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C22 N2 H2C 120.0 . . ?
C22 N2 H2D 120.0 . . ?
H2C N2 H2D 120.0 . . ?
C22 N3 H3A 120.0 . . ?
C22 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C21 N4 H4C 120.0 . . ?
C21 N4 H4D 120.0 . . ?
H4C N4 H4D 120.0 . . ?
C21 N5 H5A 120.0 . . ?
C21 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C21 N6 H6A 120.0 . . ?
C21 N6 H6B 120.0 . . ?
H6A N6 H6B 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
S1 C11 C12 C13 -177.0(2) . . . . ?
S1 C11 C16 C15 175.6(2) . . . . ?
S1 C11 C16 C17 -3.6(4) . . . . ?
O1 S1 C11 C12 1.1(3) . . . . ?
O1 S1 C11 C16 -177.1(2) . . . . ?
O2 S1 C11 C12 -118.7(3) . . . . ?
O2 S1 C11 C16 63.1(3) . . . . ?
O3 S1 C11 C12 121.6(3) . . . . ?
O3 S1 C11 C16 -56.7(3) . . . . ?
O4 S2 C20 C15 59.8(3) . . . . ?
O4 S2 C20 C19 -121.4(3) . . . . ?
O5 S2 C20 C15 -59.6(3) . . . . ?
O5 S2 C20 C19 119.2(3) . . . . ?
O6 S2 C20 C15 -179.4(2) . . . . ?
O6 S2 C20 C19 -0.7(3) . . . . ?
O7 C1 C2 C3 145.6(3) . . . . ?
O7 C1 C6 C5 -174.5(3) . . . . ?
O7 C1 C6 C7 6.6(4) . . . . ?
C1 C2 C3 C4 55.1(3) . . . . ?
C1 C2 C3 C8 -177.3(3) . . . . ?
C2 C1 C6 C5 7.3(4) . . . . ?
C2 C1 C6 C7 -171.5(3) . . . . ?
C2 C3 C4 C5 -46.9(4) . . . . ?
C2 C3 C8 C9 -128.5(4) . . . . ?
C2 C3 C8 C10 53.0(4) . . . . ?
C3 C4 C5 C6 20.6(5) . . . . ?
C4 C3 C8 C9 -3.8(4) . . . . ?
C4 C3 C8 C10 177.7(3) . . . . ?
C4 C5 C6 C1 0.7(5) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C6 C1 C2 C3 -36.2(4) . . . . ?
C8 C3 C4 C5 -173.6(3) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C11 C16 C17 C18 178.0(3) . . . . ?
C12 C11 C16 C15 -2.5(4) . . . . ?
C12 C11 C16 C17 178.3(3) . . . . ?
C12 C13 C14 C15 -1.3(5) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C13 C14 C15 C20 179.7(3) . . . . ?
C14 C15 C16 C11 2.0(4) . . . . ?
C14 C15 C16 C17 -178.7(3) . . . . ?
C14 C15 C20 S2 -1.4(4) . . . . ?
C14 C15 C20 C19 179.9(3) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C16 C11 C12 C13 1.2(5) . . . . ?
C16 C15 C20 S2 178.5(2) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 1.5(5) . . . . ?
C18 C19 C20 S2 -179.9(2) . . . . ?
C18 C19 C20 C15 -1.2(5) . . . . ?
C20 C15 C16 C11 -177.8(3) . . . . ?
C20 C15 C16 C17 1.4(4) . . . . ?

_olex2_date_sample_data_collection 2020-09-25
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.736
####################################################################### 
# 
# 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_GNPS-7
_database_code_depnum_ccdc_archive 'CCDC 2174346'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-28
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 O3 S, C8 H8 O3, C H6 N3'
_chemical_formula_sum            'C14 H17 N3 O6 S'
_chemical_formula_weight         355.36
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.2509(3)
_cell_length_b                   12.4242(3)
_cell_length_c                   18.4753(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3271.16(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4606
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5560
_cell_measurement_theta_min      2.4040
_shelx_estimated_absorpt_T_max   0.802
_shelx_estimated_absorpt_T_min   0.772
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8365
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.783
_diffrn_reflns_theta_min         4.787
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00 -21.00   1.00    1.00    --  -40.73 -36.00 -89.00   37
  2  ω     47.00  95.00   1.00    1.00    --   40.73-125.00 -60.00   48
  3  ω     70.00  96.00   1.00    1.00    --   40.73-125.00  60.00   26
  4  ω     46.00  87.00   1.00    1.00    --  107.58-107.00 179.00   41
  5  ω     67.00 122.00   1.00    1.00    --  107.58-125.00  30.00   55
  6  ω     76.00 158.00   1.00    1.00    --  107.58  77.00-180.00   82
  7  ω    105.00 141.00   1.00    1.00    --  107.58  77.00  60.00   36
  8  ω    100.00 177.00   1.00    1.00    --  107.58 125.00  60.00   77
  9  ω   -112.00 -29.00   1.00    1.00    --  -40.73 -57.00-120.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0487043000
_diffrn_orient_matrix_UB_12      0.0778628000
_diffrn_orient_matrix_UB_13      0.0529625000
_diffrn_orient_matrix_UB_21      0.0102412000
_diffrn_orient_matrix_UB_22      -0.0836783000
_diffrn_orient_matrix_UB_23      0.0610930000
_diffrn_orient_matrix_UB_31      0.0958536000
_diffrn_orient_matrix_UB_32      0.0482508000
_diffrn_orient_matrix_UB_33      0.0204957000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2718
_reflns_number_total             3241
_reflns_odcompleteness_completeness 99.82
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.056
_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)+(0.0847P)²+0.5132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1535
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C5(H5), C9(H9), C10(H10), C13(H13)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.60862(4) 0.50989(4) 0.66621(3) 0.02938(19) Uani 1 1 d . . . . .
O1 O 0.61204(11) 0.39407(13) 0.67830(10) 0.0356(4) Uani 1 1 d . . . . .
O2 O 0.53058(11) 0.56029(13) 0.70418(9) 0.0355(4) Uani 1 1 d . . . . .
O3 O 0.69802(11) 0.56148(13) 0.68238(10) 0.0362(4) Uani 1 1 d . . . . .
O4 O 0.56535(15) 0.14945(19) 0.63165(12) 0.0593(6) Uani 1 1 d . . . . .
H4 H 0.608113 0.177808 0.608892 0.089 Uiso 1 1 calc R U . . .
O5 O 0.64649(12) 0.23334(18) 0.51700(13) 0.0580(6) Uani 1 1 d . . . . .
O6 O 0.56700(13) 0.23333(17) 0.41205(13) 0.0552(5) Uani 1 1 d . . . . .
C1 C 0.49623(16) 0.15081(19) 0.51192(15) 0.0385(6) Uani 1 1 d . . . . .
C2 C 0.41922(19) 0.1230(2) 0.46910(17) 0.0458(6) Uani 1 1 d . . . . .
H2 H 0.419550 0.140318 0.420123 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3436(2) 0.0711(2) 0.49765(19) 0.0519(7) Uani 1 1 d . . . . .
H3 H 0.292626 0.053592 0.468468 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3431(2) 0.0443(2) 0.57092(19) 0.0522(7) Uani 1 1 d . . . . .
H4A H 0.291697 0.008607 0.590533 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4179(2) 0.0700(2) 0.61434(18) 0.0498(7) Uani 1 1 d . . . . .
H5 H 0.417228 0.050800 0.662995 0.060 Uiso 1 1 calc R U . . .
C6 C 0.49448(18) 0.1245(2) 0.58596(16) 0.0433(6) Uani 1 1 d . . . . .
C7 C 0.57699(18) 0.2090(2) 0.48228(16) 0.0438(6) Uani 1 1 d . . . . .
C8 C 0.6427(2) 0.2921(3) 0.3791(2) 0.0718(11) Uani 1 1 d . . . . .
H8A H 0.632267 0.296899 0.327837 0.108 Uiso 1 1 calc R U . . .
H8B H 0.700827 0.255494 0.388070 0.108 Uiso 1 1 calc R U . . .
H8C H 0.645437 0.363223 0.399304 0.108 Uiso 1 1 calc R U . . .
C9 C 0.36905(15) 0.37469(19) 0.53657(14) 0.0344(5) Uani 1 1 d . . . . .
H9 H 0.328107 0.328895 0.560821 0.041 Uiso 1 1 calc R U . . .
C10 C 0.44367(15) 0.41652(18) 0.57223(13) 0.0325(5) Uani 1 1 d . . . . .
H10 H 0.453158 0.398846 0.620591 0.039 Uiso 1 1 calc R U . . .
C11 C 0.50766(14) 0.48682(16) 0.53713(12) 0.0272(5) Uani 1 1 d . . . . .
C12 C 0.58723(14) 0.53303(17) 0.57251(13) 0.0275(4) Uani 1 1 d . . . . .
C13 C 0.64740(15) 0.60043(18) 0.53669(13) 0.0320(5) Uani 1 1 d . . . . .
H13 H 0.698868 0.629624 0.560615 0.038 Uiso 1 1 calc R U . . .
C14 C 0.63136(15) 0.84425(19) 0.72932(13) 0.0324(5) Uani 1 1 d . . . . .
N1 N 0.70544(13) 0.79193(16) 0.70497(13) 0.0410(5) Uani 1 1 d . . . . .
H1A H 0.703677 0.723058 0.700480 0.049 Uiso 1 1 calc R U . . .
H1B H 0.755496 0.826673 0.693582 0.049 Uiso 1 1 calc R U . . .
N2 N 0.63458(14) 0.95059(16) 0.73616(14) 0.0426(5) Uani 1 1 d . . . . .
H2A H 0.684805 0.985004 0.724728 0.051 Uiso 1 1 calc R U . . .
H2B H 0.586449 0.985047 0.752014 0.051 Uiso 1 1 calc R U . . .
N3 N 0.55395(13) 0.79152(16) 0.74700(12) 0.0393(5) Uani 1 1 d . . . . .
H3A H 0.551718 0.722654 0.742644 0.047 Uiso 1 1 calc R U . . .
H3B H 0.505898 0.826139 0.762849 0.047 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 1.4571(17) . ?
S1 O2 1.4564(17) . ?
S1 O3 1.4570(16) . ?
S1 C12 1.781(2) . ?
O4 H4 0.8200 . ?
O4 C6 1.352(3) . ?
O5 C7 1.218(3) . ?
O6 C7 1.340(4) . ?
O6 C8 1.438(4) . ?
C1 C2 1.396(4) . ?
C1 C6 1.407(4) . ?
C1 C7 1.465(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(5) . ?
C4 H4A 0.9300 . ?
C4 C5 1.371(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C10 1.355(3) . ?
C9 C13 1.408(3) 5_666 ?
C10 H10 0.9300 . ?
C10 C11 1.419(3) . ?
C11 C11 1.427(5) 5_666 ?
C11 C12 1.429(3) . ?
C12 C13 1.369(3) . ?
C13 H13 0.9300 . ?
C14 N1 1.319(3) . ?
C14 N2 1.328(3) . ?
C14 N3 1.324(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
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
O1 S1 O3 111.95(9) . . ?
O1 S1 C12 108.30(11) . . ?
O2 S1 O1 112.11(10) . . ?
O2 S1 O3 112.32(10) . . ?
O2 S1 C12 105.55(10) . . ?
O3 S1 C12 106.14(10) . . ?
C6 O4 H4 109.5 . . ?
C7 O6 C8 116.4(3) . . ?
C2 C1 C6 118.7(3) . . ?
C2 C1 C7 121.8(3) . . ?
C6 C1 C7 119.5(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
O4 C6 C1 122.7(3) . . ?
O4 C6 C5 117.6(3) . . ?
C5 C6 C1 119.7(2) . . ?
O5 C7 O6 122.7(3) . . ?
O5 C7 C1 124.3(3) . . ?
O6 C7 C1 112.9(2) . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 H9 119.5 . . ?
C10 C9 C13 120.9(2) . 5_666 ?
C13 C9 H9 119.5 5_666 . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C11 118.8(2) . 5_666 ?
C10 C11 C12 123.2(2) . . ?
C11 C11 C12 118.0(2) 5_666 . ?
C11 C12 S1 121.03(16) . . ?
C13 C12 S1 117.48(17) . . ?
C13 C12 C11 121.4(2) . . ?
C9 C13 H13 120.2 5_666 . ?
C12 C13 C9 119.7(2) . 5_666 ?
C12 C13 H13 120.2 . . ?
N1 C14 N2 119.7(2) . . ?
N1 C14 N3 120.5(2) . . ?
N3 C14 N2 119.8(2) . . ?
C14 N1 H1A 120.0 . . ?
C14 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C14 N2 H2A 120.0 . . ?
C14 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C14 N3 H3A 120.0 . . ?
C14 N3 H3B 120.0 . . ?
H3A N3 H3B 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
S1 C12 C13 C9 -177.03(18) . . . 5_666 ?
O1 S1 C12 C11 55.40(19) . . . . ?
O1 S1 C12 C13 -127.46(17) . . . . ?
O2 S1 C12 C11 -64.83(18) . . . . ?
O2 S1 C12 C13 112.31(17) . . . . ?
O3 S1 C12 C11 175.77(16) . . . . ?
O3 S1 C12 C13 -7.09(19) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 O4 -179.2(2) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C2 C1 C7 O5 -178.6(3) . . . . ?
C2 C1 C7 O6 1.4(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 O4 178.8(3) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C1 C7 O5 3.2(4) . . . . ?
C6 C1 C7 O6 -176.8(2) . . . . ?
C7 C1 C2 C3 -178.5(2) . . . . ?
C7 C1 C6 O4 -0.9(4) . . . . ?
C7 C1 C6 C5 179.6(2) . . . . ?
C8 O6 C7 O5 -1.0(4) . . . . ?
C8 O6 C7 C1 179.0(2) . . . . ?
C9 C10 C11 C11 -0.1(4) . . . 5_666 ?
C9 C10 C11 C12 179.9(2) . . . . ?
C10 C11 C12 S1 -3.1(3) . . . . ?
C10 C11 C12 C13 179.9(2) . . . . ?
C11 C11 C12 S1 176.9(2) 5_666 . . . ?
C11 C11 C12 C13 -0.1(3) 5_666 . . . ?
C11 C12 C13 C9 0.1(3) . . . 5_666 ?
C13 C9 C10 C11 0.1(4) 5_666 . . . ?

_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 44.708
_oxdiff_exptl_absorpt_empirical_full_min 0.411
####################################################################### 
# 
# 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_GNPS-3
_database_code_depnum_ccdc_archive 'CCDC 2174348'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H6 O6 S2), 4(C H6 N3), 2(C10 H11 O2)'
_chemical_formula_sum            'C44 H58 N12 O16 S4'
_chemical_formula_weight         1139.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           34
_space_group_name_H-M_alt        'P n n 2'
_space_group_name_Hall           'P 2 -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   8.0559(3)
_cell_length_b                   21.6299(6)
_cell_length_c                   7.2362(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1260.89(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1821
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4760
_cell_measurement_theta_min      4.0720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.444
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2776
_diffrn_reflns_point_group_measured_fraction_full 0.787
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        66.572
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         5.861
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  28.00   1.00    1.00    --  -40.73  37.00  30.00   76
  2  ω     10.00  57.00   1.00    1.00    --   40.73 -99.00-120.00   47
  3  ω     25.00  52.00   1.00    2.00    --  107.58 -94.00-180.00   27
  4  ω     79.00 174.00   1.00    2.00    --  107.58  30.00 -60.00   95
  5  ω     96.00 162.00   1.00    2.00    --  107.58 125.00-150.00   66
  6  ω     97.00 174.00   1.00    2.00    --  107.58  45.00  30.00   77
  7  ω     52.00  89.00   1.00    1.00    --   40.73-125.00  30.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0040345000
_diffrn_orient_matrix_UB_12      -0.1839617000
_diffrn_orient_matrix_UB_13      0.0572625000
_diffrn_orient_matrix_UB_21      0.0586818000
_diffrn_orient_matrix_UB_22      0.0376492000
_diffrn_orient_matrix_UB_23      0.1129411000
_diffrn_orient_matrix_UB_31      -0.0401180000
_diffrn_orient_matrix_UB_32      0.0363444000
_diffrn_orient_matrix_UB_33      0.1711982000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.451
_reflns_Friedel_fraction_full    0.535
_reflns_Friedel_fraction_max     0.535
_reflns_number_gt                1594
_reflns_number_total             1760
_reflns_odcompleteness_completeness 100.00
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.64(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1760
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.367
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1417P)²+1.4126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2208
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.36(12)
 0.64(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C4-O4
 1.45 with sigma of 0.02
 C9-C8
 1.55 with sigma of 0.02
 C5-O5 = O5-C10
 1.45 with sigma of 0.02
 C7-C8
 1.49 with sigma of 0.02
 C1-C7
 1.32 with sigma of 0.02
 C2-C1
 1.39 with sigma of 0.02
 C5-C10
 2.511 with sigma of 0.04
 C1-C7
 2.503 with sigma of 0.04
 C2-C7
 2.521 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
C9 \\sim C3 \\sim C2 \\sim C4: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C9 \\sim C8 \\sim C7: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
5. Rigid body (RIGU) restrains
 O4, O5, C9, C8, C7, C5, C3, C6, C10, C1, C2, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: O4(0.5) O5(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C8(0.5) H8(0.5)
 C7(0.5) H7(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C2(0.5) H2(0.5) C3(0.5)
 H3(0.5) C4(0.5) C5(0.5) C6(0.5) H6(0.5) C1(0.5)
7.a Riding coordinates:
 C9(H9A,H9B,H9C)
7.b Rotating group:
 N3(H3A,H3B)
7.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C8(H8), C7(H7), C2(H2), C3(H3), C6(H6)
7.d Fitted hexagon refined as free rotating group:
 C2(C3,C4,C5,C6,C1)
7.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
7.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.81749(16) -0.14313(5) 0.1879(7) 0.0341(5) Uani 1 1 d . . . . .
O2 O 0.7173(11) -0.1345(3) 0.3546(10) 0.0374(19) Uani 1 1 d . . . . .
O1 O 0.9028(5) -0.20291(17) 0.1885(17) 0.0435(11) Uani 1 1 d . . . . .
O3 O 0.7190(12) -0.1331(4) 0.0217(11) 0.042(2) Uani 1 1 d . . . . .
C14 C 0.9752(7) -0.0857(2) 0.1928(19) 0.0311(11) Uani 1 1 d . . . . .
C13 C 0.9336(6) -0.0220(2) 0.191(2) 0.0296(11) Uani 1 1 d . . . . .
C11 C 0.7355(7) 0.0623(3) 0.188(3) 0.0450(15) Uani 1 1 d . . . . .
H11 H 0.626173 0.076088 0.190766 0.054 Uiso 1 1 calc R U . . .
C12 C 0.7680(6) 0.0003(2) 0.190(2) 0.0363(12) Uani 1 1 d . . . . .
H12 H 0.680367 -0.027647 0.190111 0.044 Uiso 1 1 calc R U . . .
C15 C 1.1352(8) -0.1051(3) 0.182(2) 0.0410(14) Uani 1 1 d . . . . .
H15 H 1.158618 -0.147015 0.170088 0.049 Uiso 1 1 calc R U . . .
N1 N 0.8142(7) -0.1971(3) -0.310(2) 0.0511(15) Uani 1 1 d . . . . .
H1A H 0.784741 -0.180239 -0.207411 0.061 Uiso 1 1 calc R U . . .
H1B H 0.786711 -0.180331 -0.413249 0.061 Uiso 1 1 calc R U . . .
N2 N 0.9420(14) -0.2732(5) -0.1542(15) 0.049(3) Uani 1 1 d . . . . .
H2A H 0.911984 -0.256024 -0.052337 0.059 Uiso 1 1 calc R U . . .
H2B H 0.998991 -0.306775 -0.152227 0.059 Uiso 1 1 calc R U . . .
N3 N 0.9447(13) -0.2756(5) -0.4729(13) 0.040(2) Uani 1 1 d . . . . .
H3A H 0.879066 -0.306035 -0.498153 0.047 Uiso 1 1 d R U . . .
H3B H 0.937122 -0.248435 -0.560135 0.047 Uiso 1 1 d R U . . .
C16 C 0.9018(7) -0.2487(2) -0.309(2) 0.0377(12) Uani 1 1 d . . . . .
O4 O 0.5274(16) 0.1187(9) -0.307(5) 0.110(6) Uani 0.5 1 d D . P A -1
O5 O 0.477(2) 0.0028(11) -0.291(4) 0.105(6) Uani 0.5 1 d D . P A -1
C9 C 1.226(3) -0.1344(14) -0.301(8) 0.129(8) Uani 0.5 1 d D U P A -1
H9A H 1.338699 -0.148367 -0.312896 0.193 Uiso 0.5 1 d R U P A -1
H9B H 1.163759 -0.146487 -0.407646 0.193 Uiso 0.5 1 d R U P A -1
H9C H 1.177409 -0.152467 -0.192286 0.193 Uiso 0.5 1 d R U P A -1
C8 C 1.220(3) -0.0576(15) -0.282(4) 0.126(8) Uani 0.5 1 d D U P A -1
H8 H 1.300591 -0.033032 -0.227137 0.151 Uiso 0.5 1 calc R U P A -1
C7 C 1.071(3) -0.0357(12) -0.364(4) 0.117(8) Uani 0.5 1 d D U P A -1
H7 H 1.060281 -0.049549 -0.484960 0.141 Uiso 0.5 1 calc R U P A -1
C10 C 0.454(3) -0.0662(7) -0.298(6) 0.080(6) Uani 0.5 1 d D . P A -1
H10A H 0.542601 -0.084549 -0.366962 0.120 Uiso 0.5 1 calc R U P A -1
H10B H 0.349746 -0.075565 -0.356163 0.120 Uiso 0.5 1 calc R U P A -1
H10C H 0.453850 -0.082396 -0.174269 0.120 Uiso 0.5 1 calc R U P A -1
C2 C 0.9668(12) 0.0655(7) -0.290(4) 0.091(5) Uani 0.5 1 d DG U P A -1
H2 H 1.076228 0.078219 -0.274013 0.109 Uiso 0.5 1 calc R U P A -1
C3 C 0.8399(16) 0.1090(5) -0.294(4) 0.090(4) Uani 0.5 1 d G U P A -1
H3 H 0.864402 0.150841 -0.281612 0.108 Uiso 0.5 1 calc R U P A -1
C4 C 0.6764(13) 0.0901(6) -0.318(4) 0.074(3) Uani 0.5 1 d DG U P A -1
C5 C 0.6398(12) 0.0276(7) -0.337(4) 0.105(7) Uani 0.5 1 d DG . P A -1
C6 C 0.7667(17) -0.0159(5) -0.332(4) 0.085(5) Uani 0.5 1 d G . P A -1
H6 H 0.742248 -0.057737 -0.344569 0.102 Uiso 0.5 1 calc R U P A -1
C1 C 0.9302(14) 0.0030(6) -0.309(4) 0.085(4) Uani 0.5 1 d DG . P A -1


_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 1.463(9) . ?
S1 O1 1.464(4) . ?
S1 O3 1.457(9) . ?
S1 C14 1.777(5) . ?
C14 C13 1.419(7) . ?
C14 C15 1.358(9) . ?
C13 C13 1.430(10) 2_755 ?
C13 C12 1.419(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(8) . ?
C11 C15 1.394(8) 2_755 ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C16 1.321(7) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C16 1.278(18) . ?
N3 H3A 0.8637 . ?
N3 H3B 0.8644 . ?
N3 C16 1.368(17) . ?
O4 C4 1.353(15) . ?
O5 C10 1.50(2) . ?
O5 C5 1.45(2) . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9599 . ?
C9 C8 1.67(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.41(2) . ?
C7 H7 0.9300 . ?
C7 C1 1.468(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C2 C1 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C1 1.3900 . ?

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 111.6(6) . . ?
O2 S1 C14 106.8(5) . . ?
O1 S1 C14 106.4(2) . . ?
O3 S1 O2 111.2(2) . . ?
O3 S1 O1 112.9(6) . . ?
O3 S1 C14 107.6(6) . . ?
C13 C14 S1 120.7(4) . . ?
C15 C14 S1 117.5(4) . . ?
C15 C14 C13 121.5(5) . . ?
C14 C13 C13 118.0(6) . 2_755 ?
C12 C13 C14 123.5(5) . . ?
C12 C13 C13 118.5(6) . 2_755 ?
C12 C11 H11 119.7 . . ?
C12 C11 C15 120.6(5) . 2_755 ?
C15 C11 H11 119.7 2_755 . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 120.9(5) . . ?
C11 C12 H12 119.5 . . ?
C14 C15 C11 120.2(5) . 2_755 ?
C14 C15 H15 119.9 . . ?
C11 C15 H15 119.9 2_755 . ?
H1A N1 H1B 120.0 . . ?
C16 N1 H1A 120.0 . . ?
C16 N1 H1B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C16 N2 H2A 120.0 . . ?
C16 N2 H2B 120.0 . . ?
H3A N3 H3B 108.7 . . ?
C16 N3 H3A 110.7 . . ?
C16 N3 H3B 109.1 . . ?
N1 C16 N3 119.3(14) . . ?
N2 C16 N1 119.4(14) . . ?
N2 C16 N3 121.3(5) . . ?
C5 O5 C10 118.1(19) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H9A 110.6 . . ?
C8 C9 H9B 108.7 . . ?
C8 C9 H9C 109.2 . . ?
C9 C8 H8 125.5 . . ?
C7 C8 C9 109(2) . . ?
C7 C8 H8 125.5 . . ?
C8 C7 H7 111.5 . . ?
C8 C7 C1 137(3) . . ?
C1 C7 H7 111.5 . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
O4 C4 C3 134.4(12) . . ?
O4 C4 C5 105.2(12) . . ?
C3 C4 C5 120.0 . . ?
C4 C5 O5 121.8(14) . . ?
C6 C5 O5 114.1(14) . . ?
C6 C5 C4 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C2 C1 C7 114.7(15) . . ?
C6 C1 C7 122.1(15) . . ?
C6 C1 C2 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
S1 C14 C13 C13 -178.6(6) . . . 2_755 ?
S1 C14 C13 C12 2(2) . . . . ?
S1 C14 C15 C11 -179.0(14) . . . 2_755 ?
O2 S1 C14 C13 -61.6(13) . . . . ?
O2 S1 C14 C15 124.3(12) . . . . ?
O1 S1 C14 C13 179.0(12) . . . . ?
O1 S1 C14 C15 4.9(15) . . . . ?
O3 S1 C14 C13 57.8(13) . . . . ?
O3 S1 C14 C15 -116.3(12) . . . . ?
C14 C13 C12 C11 179.8(15) . . . . ?
C13 C14 C15 C11 7(3) . . . 2_755 ?
C13 C13 C12 C11 0.3(18) 2_755 . . . ?
C15 C14 C13 C13 -4.7(18) . . . 2_755 ?
C15 C14 C13 C12 175.7(16) . . . . ?
C15 C11 C12 C13 2(3) 2_755 . . . ?
O4 C4 C5 O5 -17(3) . . . . ?
O4 C4 C5 C6 -173(3) . . . . ?
O5 C5 C6 C1 -158(3) . . . . ?
C9 C8 C7 C1 126(4) . . . . ?
C8 C7 C1 C2 71(5) . . . . ?
C8 C7 C1 C6 -129(4) . . . . ?
C10 O5 C5 C4 -174(2) . . . . ?
C10 O5 C5 C6 -17(3) . . . . ?
C2 C3 C4 O4 171(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C2 C1 C7 160(2) . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C3 C4 C5 O5 156(3) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C5 C6 C1 C7 -159(3) . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?

_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 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.653
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.36(12)
2 0.64(12)

####################################################################### 
# 
# 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_GNPS-6
_database_code_depnum_ccdc_archive 'CCDC 2174345'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 O6 S2, C12 H19 N, 2(C H6 N3)'
_chemical_formula_sum            'C24 H37 N7 O6 S2'
_chemical_formula_weight         583.72
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.0691(9)
_cell_length_b                   12.2502(9)
_cell_length_c                   19.5115(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3123.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3462
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.8120
_cell_measurement_theta_min      3.3160
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11388
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.557
_diffrn_reflns_theta_min         2.088
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  -2.00   1.00    3.25    --  -11.59 -37.00  90.00   60
  2  ω    -13.00  29.00   1.00    3.25    --  -11.59 -99.00  30.00   42
  3  ω     34.00  77.00   1.00    3.25    --   11.74-178.00 -30.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0405154000
_diffrn_orient_matrix_UB_12      0.0251169000
_diffrn_orient_matrix_UB_13      0.0184162000
_diffrn_orient_matrix_UB_21      0.0357476000
_diffrn_orient_matrix_UB_22      0.0211162000
_diffrn_orient_matrix_UB_23      0.0239820000
_diffrn_orient_matrix_UB_31      0.0053793000
_diffrn_orient_matrix_UB_32      0.0477561000
_diffrn_orient_matrix_UB_33      -0.0201072000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2688
_reflns_number_total             3843
_reflns_odcompleteness_completeness 99.92
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     118
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.088
_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)+(0.0758P)²+1.2044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11-C10 = C10-C12 = C9-C7 = C8-C7
 1.52 with sigma of 0.02
 N4-C1
 1.48 with sigma of 0.02
 C10-C6 = C7-C2
 1.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, N4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: C1(0.5) C2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5)
 C6(0.5) C7(0.5) H7(0.5) C8(0.5) H8A(0.5) H8B(0.5) H8C(0.5) C9(0.5) H9A(0.5)
 H9B(0.5) H9C(0.5) C10(0.5) H10(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
 C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) N4(0.5) H4A(0.5) H4B(0.5)
6.a Rotating group:
 N4(H4A,H4B)
6.b Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15)
6.d Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6)
6.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B)
6.f Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.57943(4) 0.59163(4) 0.65712(3) 0.0334(2) Uani 1 1 d . . . . .
O1 O 0.58678(11) 0.70520(13) 0.67844(9) 0.0380(4) Uani 1 1 d . . . . .
O2 O 0.50349(12) 0.53110(12) 0.69644(8) 0.0403(4) Uani 1 1 d . . . . .
O3 O 0.67912(12) 0.53823(13) 0.65745(9) 0.0406(4) Uani 1 1 d . . . . .
C1 C 0.9663(2) 0.4963(4) 0.52583(14) 0.0337(8) Uani 0.5 1 d DG . P A -1
C2 C 0.9191(2) 0.5044(3) 0.46220(16) 0.0307(14) Uani 0.5 1 d DG . P A -1
C3 C 0.9779(2) 0.5067(3) 0.40286(14) 0.0386(10) Uani 0.5 1 d G . P A -1
H3 H 0.946282 0.512098 0.360287 0.046 Uiso 0.5 1 calc R U P A -1
C4 C 1.0839(2) 0.5009(4) 0.40715(16) 0.042(2) Uani 0.5 1 d G . P A -1
H4 H 1.123249 0.502499 0.367440 0.051 Uiso 0.5 1 calc R U P A -1
C5 C 1.1311(2) 0.4929(3) 0.47078(19) 0.0416(10) Uani 0.5 1 d G . P A -1
H5 H 1.202074 0.489030 0.473642 0.050 Uiso 0.5 1 calc R U P A -1
C6 C 1.0723(2) 0.4906(3) 0.53012(15) 0.0417(18) Uani 0.5 1 d DG . P A -1
C7 C 0.8024(3) 0.5057(4) 0.4551(3) 0.0479(11) Uani 0.5 1 d D U P A -1
H7 H 0.780325 0.514974 0.502775 0.057 Uiso 0.5 1 calc R U P A -1
C8 C 0.7692(10) 0.6043(11) 0.4246(9) 0.160(6) Uani 0.5 1 d D U P A -1
H8A H 0.824207 0.656180 0.424878 0.240 Uiso 0.5 1 calc R U P A -1
H8B H 0.712407 0.633043 0.450110 0.240 Uiso 0.5 1 calc R U P A -1
H8C H 0.748357 0.590474 0.378268 0.240 Uiso 0.5 1 calc R U P A -1
C9 C 0.7605(6) 0.3974(7) 0.4380(7) 0.143(4) Uani 0.5 1 d D U P A -1
H9A H 0.771083 0.382877 0.390189 0.214 Uiso 0.5 1 calc R U P A -1
H9B H 0.688506 0.396168 0.447865 0.214 Uiso 0.5 1 calc R U P A -1
H9C H 0.794470 0.342626 0.464832 0.214 Uiso 0.5 1 calc R U P A -1
C10 C 1.1234(5) 0.4795(6) 0.5997(3) 0.0663(14) Uani 0.5 1 d D . P A -1
H10 H 1.076713 0.436687 0.628379 0.080 Uiso 0.5 1 calc R U P A -1
C11 C 1.1329(7) 0.5913(7) 0.6334(5) 0.100(3) Uani 0.5 1 d D . P A -1
H11A H 1.180072 0.635361 0.607789 0.150 Uiso 0.5 1 calc R U P A -1
H11B H 1.157534 0.582712 0.679447 0.150 Uiso 0.5 1 calc R U P A -1
H11C H 1.067124 0.626090 0.634209 0.150 Uiso 0.5 1 calc R U P A -1
C12 C 1.2289(9) 0.4295(11) 0.6085(5) 0.094(3) Uani 0.5 1 d D . P A -1
H12A H 1.227885 0.355178 0.592938 0.141 Uiso 0.5 1 calc R U P A -1
H12B H 1.247836 0.431446 0.656058 0.141 Uiso 0.5 1 calc R U P A -1
H12C H 1.277788 0.470280 0.582176 0.141 Uiso 0.5 1 calc R U P A -1
C13 C 0.46835(19) 0.60992(18) 0.43717(13) 0.0405(6) Uani 1 1 d . . . . .
H13 H 0.445615 0.616280 0.392185 0.049 Uiso 1 1 calc R U . . .
C14 C 0.4869(2) 0.70175(19) 0.47390(14) 0.0479(7) Uani 1 1 d . . . . .
H14 H 0.476743 0.769851 0.453975 0.058 Uiso 1 1 calc R U . . .
C15 C 0.52148(18) 0.69455(18) 0.54179(13) 0.0391(6) Uani 1 1 d . . . . .
H15 H 0.534194 0.757854 0.566681 0.047 Uiso 1 1 calc R U . . .
C16 C 0.53651(16) 0.59490(16) 0.57145(12) 0.0312(5) Uani 1 1 d . . . . .
C17 C 0.51731(16) 0.49593(16) 0.53436(11) 0.0303(5) Uani 1 1 d . . . . .
C18 C 0.35015(17) 0.76124(19) 0.77518(12) 0.0357(5) Uani 1 1 d . . . . .
N1 N 0.27852(15) 0.81412(16) 0.80952(12) 0.0471(6) Uani 1 1 d . . . . .
H1A H 0.223915 0.780577 0.822227 0.056 Uiso 1 1 calc R U . . .
H1B H 0.286484 0.882093 0.819157 0.056 Uiso 1 1 calc R U . . .
N2 N 0.43424(15) 0.81312(16) 0.75575(11) 0.0420(5) Uani 1 1 d . . . . .
H2A H 0.481003 0.778817 0.733440 0.050 Uiso 1 1 calc R U . . .
H2B H 0.442050 0.881092 0.765443 0.050 Uiso 1 1 calc R U . . .
N3 N 0.33768(16) 0.65689(16) 0.76047(11) 0.0439(5) Uani 1 1 d . . . . .
H3A H 0.283016 0.623508 0.773227 0.053 Uiso 1 1 calc R U . . .
H3B H 0.384219 0.622306 0.738119 0.053 Uiso 1 1 calc R U . . .
N4 N 0.9049(4) 0.4891(6) 0.5848(3) 0.0465(18) Uani 0.5 1 d D . P A -1
H4A H 0.913028 0.426462 0.604019 0.056 Uiso 0.5 1 d R U P A -1
H4B H 0.923568 0.539652 0.612789 0.056 Uiso 0.5 1 d R U P A -1


_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 1.4553(16) . ?
S1 O2 1.4572(16) . ?
S1 O3 1.4579(16) . ?
S1 C16 1.764(2) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 N4 1.406(4) . ?
C2 C3 1.3900 . ?
C2 C7 1.531(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 C10 1.519(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.414(11) . ?
C7 C9 1.474(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.524(9) . ?
C10 C12 1.519(11) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.356(3) . ?
C13 C17 1.423(3) 5_666 ?
C14 H14 0.9300 . ?
C14 C15 1.402(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(3) . ?
C16 C17 1.434(3) . ?
C17 C17 1.419(4) 5_666 ?
C18 N1 1.321(3) . ?
C18 N2 1.325(3) . ?
C18 N3 1.320(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8607 . ?
N4 H4B 0.8604 . ?

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 112.40(9) . . ?
O1 S1 O3 111.64(9) . . ?
O1 S1 C16 105.67(10) . . ?
O2 S1 O3 112.22(10) . . ?
O2 S1 C16 107.09(10) . . ?
O3 S1 C16 107.37(10) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 N4 118.8(3) . . ?
C6 C1 N4 121.1(3) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 C7 121.6(3) . . ?
C3 C2 C7 118.4(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C10 119.8(3) . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C10 120.2(3) . . ?
C2 C7 H7 102.1 . . ?
C8 C7 C2 110.7(7) . . ?
C8 C7 H7 102.1 . . ?
C8 C7 C9 124.0(10) . . ?
C9 C7 C2 112.4(5) . . ?
C9 C7 H7 102.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10 106.5 . . ?
C6 C10 C11 110.0(5) . . ?
C6 C10 C12 122.4(6) . . ?
C11 C10 H10 106.5 . . ?
C12 C10 H10 106.5 . . ?
C12 C10 C11 103.8(7) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13 119.1 . . ?
C14 C13 C17 121.7(2) . 5_666 ?
C17 C13 H13 119.1 5_666 . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 S1 117.90(17) . . ?
C15 C16 C17 121.1(2) . . ?
C17 C16 S1 120.98(16) . . ?
C13 C17 C16 123.4(2) 5_666 . ?
C17 C17 C13 118.4(2) 5_666 5_666 ?
C17 C17 C16 118.3(2) 5_666 . ?
N1 C18 N2 119.9(2) . . ?
N3 C18 N1 119.8(2) . . ?
N3 C18 N2 120.3(2) . . ?
C18 N1 H1A 120.0 . . ?
C18 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C18 N2 H2A 120.0 . . ?
C18 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C18 N3 H3A 120.0 . . ?
C18 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 N4 H4A 110.0 . . ?
C1 N4 H4B 108.2 . . ?
H4A N4 H4B 109.3 . . ?

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
S1 C16 C17 C13 -0.4(3) . . . 5_666 ?
S1 C16 C17 C17 179.9(2) . . . 5_666 ?
O1 S1 C16 C15 1.6(2) . . . . ?
O1 S1 C16 C17 -177.96(16) . . . . ?
O2 S1 C16 C15 121.61(18) . . . . ?
O2 S1 C16 C17 -57.94(19) . . . . ?
O3 S1 C16 C15 -117.69(18) . . . . ?
O3 S1 C16 C17 62.77(19) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C2 C7 C8 119.1(9) . . . . ?
C1 C2 C7 C9 -97.6(7) . . . . ?
C1 C6 C10 C11 -82.4(6) . . . . ?
C1 C6 C10 C12 155.4(8) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 C10 -178.8(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C2 C7 C8 -63.6(10) . . . . ?
C3 C2 C7 C9 79.7(8) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C10 178.8(4) . . . . ?
C5 C6 C10 C11 98.8(6) . . . . ?
C5 C6 C10 C12 -23.4(9) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C1 C2 C7 177.2(3) . . . . ?
C7 C2 C3 C4 -177.3(3) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 S1 -179.69(19) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C13 -180.0(2) . . . 5_666 ?
C15 C16 C17 C17 0.3(4) . . . 5_666 ?
C17 C13 C14 C15 0.1(4) 5_666 . . . ?
N4 C1 C2 C3 -177.1(6) . . . . ?
N4 C1 C2 C7 0.1(5) . . . . ?
N4 C1 C6 C5 177.1(6) . . . . ?
N4 C1 C6 C10 -1.7(6) . . . . ?

_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 1.542
_oxdiff_exptl_absorpt_empirical_full_min 0.661
####################################################################### 
# 
# 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_GNPS-5
_database_code_depnum_ccdc_archive 'CCDC 2174349'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 O6 S2, 2(C6 H7.5 O), 2(C H6 N3)'
_chemical_formula_sum            'C24 H33 N6 O8 S2'
_chemical_formula_weight         597.68
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.0361(3)
_cell_length_b                   12.2207(2)
_cell_length_c                   19.6245(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3126.38(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3744
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6880
_cell_measurement_theta_min      5.4290
_shelx_estimated_absorpt_T_max   0.810
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7703
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         5.450
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  42.00   1.00    1.00    --   40.73 -99.00 -30.00   41
  2  ω     35.00 108.00   1.00    2.00    --  107.58 -94.00  30.00   73
  3  ω     34.00 122.00   1.00    2.00    --  107.58-125.00 -30.00   88
  4  ω     85.00 156.00   1.00    2.00    --  107.58  45.00 -30.00   71
  5  ω    130.00 165.00   1.00    2.00    --  107.58 120.00-134.00   35
  6  ω    109.00 158.00   1.00    2.00    --  107.58 125.00 -30.00   49
  7  ω     75.00 113.00   1.00    1.00    --   40.73  57.00-180.00   38
  8  ω    -95.00  -2.00   1.00    1.00    --  -40.73 125.00 150.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0017977000
_diffrn_orient_matrix_UB_12      -0.1249098000
_diffrn_orient_matrix_UB_13      0.0105443000
_diffrn_orient_matrix_UB_21      -0.0978768000
_diffrn_orient_matrix_UB_22      -0.0079507000
_diffrn_orient_matrix_UB_23      -0.0436517000
_diffrn_orient_matrix_UB_31      0.0661269000
_diffrn_orient_matrix_UB_32      -0.0150109000
_diffrn_orient_matrix_UB_33      -0.0644242000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2347
_reflns_number_total             2743
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.785
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0793
_refine_ls_restrained_S_all      1.159
_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)+(0.1695P)²+4.2907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2495
_refine_ls_wR_factor_ref         0.2628
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C8
 1.35 with sigma of 0.02
 O5-C11 = O4-C10
 1.42 with sigma of 0.04
 O5-C2 = O4-C1
 1.42 with sigma of 0.04
 C8-C9
 1.52 with sigma of 0.02
 C7-C4
 1.52 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 O4, O5, C4, C3, C2, C1, C6, C5, C7, C8, C9, C10, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O4(0.5) O5(0.5) C4(0.5) C3(0.5) H3(0.5) C2(0.5) C1(0.5) C5(0.5)
 H5(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
6.a Riding coordinates:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5), C7(H7), C8(H8), C12(H12), C15(H15), C16(H16)
6.c Fitted hexagon refined as free rotating group:
 C4(C3,C2,C1,C6,C5)
6.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B)
6.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_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 1.07908(7) 0.90766(7) 0.34344(4) 0.0294(4) Uani 1 1 d . . . . .
O1 O 1.1790(2) 0.9613(2) 0.34313(13) 0.0371(7) Uani 1 1 d . . . . .
O2 O 1.0030(2) 0.9684(2) 0.30419(13) 0.0363(7) Uani 1 1 d . . . . .
O3 O 1.08605(19) 0.7940(2) 0.32224(14) 0.0341(7) Uani 1 1 d . . . . .
O4 O 0.8975(7) 0.5214(11) 0.3940(5) 0.083(2) Uani 0.5 1 d D . P A -1
O5 O 0.8002(5) 0.5079(7) 0.4531(4) 0.0657(18) Uani 0.5 1 d D . P A -1
C4 C 1.0711(4) 0.4887(5) 0.53226(16) 0.036(2) Uani 0.5 1 d DG U P A -1
C3 C 0.9650(4) 0.4937(5) 0.5258(2) 0.0327(12) Uani 0.5 1 d G U P A -1
H3 H 0.923655 0.489904 0.564322 0.039 Uiso 0.5 1 calc R U P A -1
C2 C 0.9207(3) 0.5042(5) 0.4617(2) 0.0372(19) Uani 0.5 1 d DG U P A -1
C1 C 0.9825(3) 0.5099(4) 0.40407(19) 0.0412(14) Uani 0.5 1 d DG U P A -1
C6 C 1.0886(3) 0.5050(3) 0.41055(16) 0.0405(9) Uani 1 1 d G U . A -1
H6 H 1.129945 0.508728 0.372000 0.049 Uiso 1 1 calc R U . A -1
C5 C 1.1329(3) 0.4944(4) 0.47464(19) 0.0375(13) Uani 0.5 1 d G U P A -1
H5 H 1.203854 0.491092 0.478981 0.045 Uiso 0.5 1 calc R U P A -1
C7 C 1.1407(10) 0.4782(15) 0.5966(7) 0.081(3) Uani 0.5 1 d D U P A -1
H7 H 1.118550 0.516932 0.634671 0.097 Uiso 0.5 1 calc R U P A -1
C8 C 1.2282(7) 0.4214(9) 0.6051(6) 0.060(2) Uani 0.5 1 d D U P A -1
H8 H 1.272552 0.415779 0.642056 0.072 Uiso 0.5 1 calc R U P A -1
C9 C 1.2307(16) 0.373(2) 0.5395(8) 0.125(6) Uani 0.5 1 d D U P A -1
H9A H 1.275269 0.432426 0.527816 0.188 Uiso 0.5 1 d R U P A -1
H9B H 1.271019 0.310676 0.552836 0.188 Uiso 0.5 1 d R U P A -1
H9C H 1.189329 0.353886 0.500756 0.188 Uiso 0.5 1 d R U P A -1
C10 C 0.8712(10) 0.4149(13) 0.3645(6) 0.084(3) Uani 0.5 1 d D . P A -1
H10A H 0.797880 0.418893 0.368240 0.125 Uiso 0.5 1 d R U P A -1
H10B H 0.894820 0.347113 0.383600 0.125 Uiso 0.5 1 d R U P A -1
H10C H 0.890680 0.418873 0.317430 0.125 Uiso 0.5 1 d R U P A -1
C11 C 0.7602(9) 0.3949(11) 0.4522(9) 0.085(4) Uani 0.5 1 d D . P A -1
H11A H 0.796003 0.353240 0.418198 0.127 Uiso 0.5 1 calc R U P A -1
H11B H 0.688319 0.396105 0.441693 0.127 Uiso 0.5 1 calc R U P A -1
H11C H 0.770375 0.361874 0.496061 0.127 Uiso 0.5 1 calc R U P A -1
C12 C 1.0216(3) 0.8045(3) 0.4589(2) 0.0361(9) Uani 1 1 d . . . . .
H12 H 1.033533 0.741096 0.433953 0.043 Uiso 1 1 calc R U . . .
C13 C 1.0364(3) 0.9051(3) 0.42950(19) 0.0285(8) Uani 1 1 d . . . . .
C14 C 1.0175(3) 1.0042(3) 0.46555(18) 0.0284(8) Uani 1 1 d . . . . .
C15 C 1.0311(3) 1.1099(3) 0.4371(2) 0.0375(9) Uani 1 1 d . . . . .
H15 H 1.053864 1.116204 0.392351 0.045 Uiso 1 1 calc R U . . .
C16 C 1.0116(4) 1.2022(3) 0.4734(2) 0.0425(10) Uani 1 1 d . . . . .
H16 H 1.020427 1.270403 0.453161 0.051 Uiso 1 1 calc R U . . .
C17 C 0.8500(3) 0.7381(3) 0.22440(18) 0.0330(8) Uani 1 1 d . . . . .
N1 N 0.7787(3) 0.6852(3) 0.18949(18) 0.0408(8) Uani 1 1 d . . . . .
H1A H 0.724166 0.718845 0.176557 0.049 Uiso 1 1 calc R U . . .
H1B H 0.786983 0.617156 0.179734 0.049 Uiso 1 1 calc R U . . .
N2 N 0.9344(3) 0.6861(3) 0.24354(17) 0.0376(8) Uani 1 1 d . . . . .
H2A H 0.981201 0.720324 0.265835 0.045 Uiso 1 1 calc R U . . .
H2B H 0.942272 0.618028 0.233670 0.045 Uiso 1 1 calc R U . . .
N3 N 0.8373(3) 0.8428(3) 0.23941(17) 0.0385(8) Uani 1 1 d . . . . .
H3A H 0.782768 0.876445 0.226478 0.046 Uiso 1 1 calc R U . . .
H3B H 0.883667 0.877180 0.262098 0.046 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 1.459(3) . ?
S1 O2 1.459(3) . ?
S1 O3 1.453(3) . ?
S1 C13 1.778(4) . ?
O4 C1 1.135(9) . ?
O4 C10 1.465(17) . ?
O5 C2 1.580(7) . ?
O5 C11 1.476(14) . ?
C4 C3 1.3900 . ?
C4 C5 1.3900 . ?
C4 C7 1.561(14) . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 C1 1.3900 . ?
C1 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.345(13) . ?
C8 H8 0.9300 . ?
C8 C9 1.419(15) . ?
C9 H9A 0.9599 . ?
C9 H9B 0.9602 . ?
C9 H9C 0.9599 . ?
C10 H10A 0.9599 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9601 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.371(5) . ?
C12 C16 1.400(6) 5_776 ?
C13 C14 1.424(5) . ?
C14 C14 1.431(7) 5_776 ?
C14 C15 1.419(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.358(5) . ?
C16 H16 0.9300 . ?
C17 N1 1.323(5) . ?
C17 N2 1.325(5) . ?
C17 N3 1.323(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
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
O1 S1 O2 112.09(15) . . ?
O1 S1 C13 106.93(16) . . ?
O2 S1 C13 107.33(16) . . ?
O3 S1 O1 111.89(15) . . ?
O3 S1 O2 112.21(15) . . ?
O3 S1 C13 105.94(16) . . ?
C1 O4 C10 100.8(10) . . ?
C11 O5 C2 109.0(7) . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C7 131.0(6) . . ?
C5 C4 C7 109.0(6) . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C2 O5 120.8(4) . . ?
C1 C2 O5 119.2(4) . . ?
C1 C2 C3 120.0 . . ?
O4 C1 C2 65.2(6) . . ?
O4 C1 C6 173.3(7) . . ?
C6 C1 C2 120.0 . . ?
C1 C6 H6 120.0 . . ?
C1 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C7 H7 115.3 . . ?
C8 C7 C4 129.5(13) . . ?
C8 C7 H7 115.3 . . ?
C7 C8 H8 131.5 . . ?
C7 C8 C9 97.1(12) . . ?
C9 C8 H8 131.5 . . ?
C8 C9 H9A 85.0 . . ?
C8 C9 H9B 95.5 . . ?
C8 C9 H9C 143.8 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 H10A 99.1 . . ?
O4 C10 H10B 122.6 . . ?
O4 C10 H10C 105.9 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C16 119.7(3) . 5_776 ?
C16 C12 H12 120.1 5_776 . ?
C12 C13 S1 117.3(3) . . ?
C12 C13 C14 121.9(3) . . ?
C14 C13 S1 120.7(3) . . ?
C13 C14 C14 117.6(4) . 5_776 ?
C15 C14 C13 123.9(3) . . ?
C15 C14 C14 118.5(4) . 5_776 ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.8(4) . . ?
C16 C15 H15 119.1 . . ?
C12 C16 H16 119.8 5_776 . ?
C15 C16 C12 120.4(3) . 5_776 ?
C15 C16 H16 119.8 . . ?
N1 C17 N2 119.7(3) . . ?
N3 C17 N1 120.0(3) . . ?
N3 C17 N2 120.3(3) . . ?
C17 N1 H1A 120.0 . . ?
C17 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C17 N2 H2A 120.0 . . ?
C17 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C17 N3 H3A 120.0 . . ?
C17 N3 H3B 120.0 . . ?
H3A N3 H3B 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
S1 C13 C14 C14 179.5(3) . . . 5_776 ?
S1 C13 C14 C15 -0.3(5) . . . . ?
O1 S1 C13 C12 -117.9(3) . . . . ?
O1 S1 C13 C14 62.9(3) . . . . ?
O2 S1 C13 C12 121.7(3) . . . . ?
O2 S1 C13 C14 -57.5(3) . . . . ?
O3 S1 C13 C12 1.6(3) . . . . ?
O3 S1 C13 C14 -177.6(3) . . . . ?
O5 C2 C1 O4 5.8(8) . . . . ?
O5 C2 C1 C6 -178.9(5) . . . . ?
C4 C3 C2 O5 178.9(5) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C4 C7 C8 C9 -3(2) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C7 C8 142.1(12) . . . . ?
C3 C2 C1 O4 -175.3(8) . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C5 C4 C7 C8 -38.5(19) . . . . ?
C7 C4 C3 C2 179.4(10) . . . . ?
C7 C4 C5 C6 -179.5(8) . . . . ?
C10 O4 C1 C2 -104.3(9) . . . . ?
C11 O5 C2 C3 -83.2(9) . . . . ?
C11 O5 C2 C1 95.7(9) . . . . ?
C12 C13 C14 C14 0.3(6) . . . 5_776 ?
C12 C13 C14 C15 -179.5(4) . . . . ?
C13 C14 C15 C16 179.7(4) . . . . ?
C14 C14 C15 C16 -0.1(7) 5_776 . . . ?
C14 C15 C16 C12 0.8(7) . . . 5_776 ?
C16 C12 C13 S1 179.8(3) 5_776 . . . ?
C16 C12 C13 C14 -1.0(6) 5_776 . . . ?

_olex2_date_sample_data_collection 2020-09-26
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.830
####################################################################### 
# 
# 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_GNPS-4
_database_code_depnum_ccdc_archive 'CCDC 2174351'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 O3 S, C8 H11 N, C H6 N3'
_chemical_formula_sum            'C14 H20 N4 O3 S'
_chemical_formula_weight         324.40
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.9018(7)
_cell_length_b                   12.5517(6)
_cell_length_c                   18.8575(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3290.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8450
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.1990
_cell_measurement_theta_min      3.0410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20420
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.160
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  36.00   1.00    5.00    --   11.90 -57.00 -60.00   96
  2  ω    -18.00  78.00   1.00    5.00    --   11.90  77.00-150.00   96
  3  ω    -16.00  78.00   1.00    5.00    --   11.90  57.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213554000
_diffrn_orient_matrix_UB_12      0.0158433000
_diffrn_orient_matrix_UB_13      0.0325070000
_diffrn_orient_matrix_UB_21      -0.0242858000
_diffrn_orient_matrix_UB_22      -0.0419085000
_diffrn_orient_matrix_UB_23      0.0177067000
_diffrn_orient_matrix_UB_31      0.0394401000
_diffrn_orient_matrix_UB_32      -0.0344568000
_diffrn_orient_matrix_UB_33      -0.0066929000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2602
_reflns_number_total             2898
_reflns_odcompleteness_completeness 99.87
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.058
_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)+(0.0446P)²+1.1801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0851
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C13(H13)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.40436(3) 0.51720(3) 0.66853(2) 0.01677(12) Uani 1 1 d . . . . .
O1 O 0.31325(7) 0.56752(8) 0.68816(5) 0.0214(2) Uani 1 1 d . . . . .
O2 O 0.48641(7) 0.56897(8) 0.70288(5) 0.0217(2) Uani 1 1 d . . . . .
O3 O 0.40267(7) 0.40216(8) 0.68072(5) 0.0203(2) Uani 1 1 d . . . . .
C1 C 0.87611(11) 0.47321(13) 0.50394(9) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.90342(11) 0.37240(13) 0.47856(9) 0.0267(4) Uani 1 1 d . . . . .
C3 C 0.91543(12) 0.28974(14) 0.52680(10) 0.0346(4) Uani 1 1 d . . . . .
H3 H 0.933516 0.222841 0.510330 0.042 Uiso 1 1 calc R U . . .
C4 C 0.90111(13) 0.30461(15) 0.59891(10) 0.0381(5) Uani 1 1 d . . . . .
H4 H 0.910606 0.248725 0.630525 0.046 Uiso 1 1 calc R U . . .
C5 C 0.87243(13) 0.40393(15) 0.62324(9) 0.0355(4) Uani 1 1 d . . . . .
H5 H 0.862425 0.414076 0.671538 0.043 Uiso 1 1 calc R U . . .
C6 C 0.85827(12) 0.48900(13) 0.57669(9) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.82126(15) 0.59477(15) 0.60351(11) 0.0436(5) Uani 1 1 d . . . . .
H7A H 0.866330 0.649912 0.591656 0.065 Uiso 1 1 calc R U . . .
H7B H 0.813632 0.591573 0.654058 0.065 Uiso 1 1 calc R U . . .
H7C H 0.760303 0.610014 0.581845 0.065 Uiso 1 1 calc R U . . .
C8 C 0.91776(13) 0.35434(16) 0.40002(10) 0.0376(4) Uani 1 1 d . . . . .
H8A H 0.859457 0.371325 0.375189 0.056 Uiso 1 1 calc R U . . .
H8B H 0.934066 0.281054 0.391790 0.056 Uiso 1 1 calc R U . . .
H8C H 0.968850 0.399158 0.383203 0.056 Uiso 1 1 calc R U . . .
C9 C 0.64410(10) 0.38600(12) 0.53234(8) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.690587 0.345074 0.555045 0.025 Uiso 1 1 calc R U . . .
C10 C 0.57034(11) 0.42905(12) 0.57077(8) 0.0189(3) Uani 1 1 d . . . . .
H10 H 0.567685 0.417621 0.619460 0.023 Uiso 1 1 calc R U . . .
C11 C 0.49754(10) 0.49111(11) 0.53742(7) 0.0153(3) Uani 1 1 d . . . . .
C12 C 0.41807(10) 0.53730(11) 0.57521(8) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.34971(10) 0.59698(12) 0.54111(8) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.299027 0.626314 0.566702 0.024 Uiso 1 1 calc R U . . .
C14 C 0.35875(11) 0.84473(12) 0.72934(8) 0.0208(3) Uani 1 1 d . . . . .
N1 N 0.35438(10) 0.94945(10) 0.73756(7) 0.0278(3) Uani 1 1 d . . . . .
H1A H 0.303522 0.983600 0.725021 0.033 Uiso 1 1 calc R U . . .
H1B H 0.402406 0.983266 0.755441 0.033 Uiso 1 1 calc R U . . .
N2 N 0.28448(9) 0.79286(11) 0.70173(7) 0.0297(3) Uani 1 1 d . . . . .
H2A H 0.233715 0.827218 0.689236 0.036 Uiso 1 1 calc R U . . .
H2B H 0.287122 0.724891 0.696333 0.036 Uiso 1 1 calc R U . . .
N3 N 0.43678(9) 0.79146(10) 0.74919(7) 0.0245(3) Uani 1 1 d . . . . .
H3A H 0.484724 0.824935 0.767469 0.029 Uiso 1 1 calc R U . . .
H3B H 0.439356 0.723487 0.743775 0.029 Uiso 1 1 calc R U . . .
N4 N 0.85957(12) 0.55618(13) 0.45544(10) 0.0346(4) Uani 1 1 d . . . . .
H4A H 0.8616(15) 0.6211(19) 0.4744(11) 0.045(6) Uiso 1 1 d . . . . .
H4B H 0.8938(16) 0.5535(18) 0.4158(14) 0.057(7) Uiso 1 1 d . . . . .


_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 1.4629(11) . ?
S1 O2 1.4638(11) . ?
S1 O3 1.4624(11) . ?
S1 C12 1.7880(15) . ?
C1 C2 1.405(2) . ?
C1 C6 1.408(2) . ?
C1 N4 1.405(2) . ?
C2 C3 1.390(2) . ?
C2 C8 1.511(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(2) . ?
C6 C7 1.511(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C10 1.367(2) . ?
C9 C13 1.404(2) 5_666 ?
C10 H10 0.9300 . ?
C10 C11 1.424(2) . ?
C11 C11 1.430(3) 5_666 ?
C11 C12 1.437(2) . ?
C12 C13 1.370(2) . ?
C13 H13 0.9300 . ?
C14 N1 1.325(2) . ?
C14 N2 1.327(2) . ?
C14 N3 1.328(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.89(2) . ?
N4 H4B 0.89(3) . ?

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 111.78(6) . . ?
O1 S1 C12 106.29(6) . . ?
O2 S1 C12 106.85(6) . . ?
O3 S1 O1 111.88(6) . . ?
O3 S1 O2 112.41(6) . . ?
O3 S1 C12 107.20(6) . . ?
C2 C1 C6 120.41(15) . . ?
N4 C1 C2 119.34(16) . . ?
N4 C1 C6 120.07(16) . . ?
C1 C2 C8 120.30(16) . . ?
C3 C2 C1 118.80(16) . . ?
C3 C2 C8 120.90(16) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.60(17) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.12(17) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.32(17) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 120.65(16) . . ?
C5 C6 C1 118.70(16) . . ?
C5 C6 C7 120.62(16) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C13 120.59(13) . 5_666 ?
C13 C9 H9 119.7 5_666 . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.02(13) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C11 119.16(16) . 5_666 ?
C10 C11 C12 123.25(13) . . ?
C11 C11 C12 117.58(16) 5_666 . ?
C11 C12 S1 120.87(11) . . ?
C13 C12 S1 117.72(11) . . ?
C13 C12 C11 121.41(13) . . ?
C9 C13 H13 119.9 5_666 . ?
C12 C13 C9 120.24(13) . 5_666 ?
C12 C13 H13 119.9 . . ?
N1 C14 N2 119.80(14) . . ?
N1 C14 N3 120.26(14) . . ?
N2 C14 N3 119.94(14) . . ?
C14 N1 H1A 120.0 . . ?
C14 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C14 N2 H2A 120.0 . . ?
C14 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C14 N3 H3A 120.0 . . ?
C14 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 N4 H4A 114.3(13) . . ?
C1 N4 H4B 115.6(15) . . ?
H4A N4 H4B 111(2) . . ?

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
S1 C12 C13 C9 -178.98(11) . . . 5_666 ?
O1 S1 C12 C11 -175.67(11) . . . . ?
O1 S1 C12 C13 3.55(13) . . . . ?
O2 S1 C12 C11 64.83(13) . . . . ?
O2 S1 C12 C13 -115.94(12) . . . . ?
O3 S1 C12 C11 -55.88(13) . . . . ?
O3 S1 C12 C13 123.34(12) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C1 C6 C5 2.8(2) . . . . ?
C2 C1 C6 C7 -175.09(15) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 176.28(17) . . . . ?
C6 C1 C2 C3 -2.0(2) . . . . ?
C6 C1 C2 C8 176.97(15) . . . . ?
C8 C2 C3 C4 -178.99(15) . . . . ?
C9 C10 C11 C11 -0.4(2) . . . 5_666 ?
C9 C10 C11 C12 179.41(14) . . . . ?
C10 C11 C12 S1 -1.11(19) . . . . ?
C10 C11 C12 C13 179.69(14) . . . . ?
C11 C11 C12 S1 178.70(13) 5_666 . . . ?
C11 C11 C12 C13 -0.5(2) 5_666 . . . ?
C11 C12 C13 C9 0.2(2) . . . 5_666 ?
C13 C9 C10 C11 0.7(2) 5_666 . . . ?
N4 C1 C2 C3 -177.18(15) . . . . ?
N4 C1 C2 C8 1.8(2) . . . . ?
N4 C1 C6 C5 177.94(15) . . . . ?
N4 C1 C6 C7 0.0(2) . . . . ?

_olex2_date_sample_data_collection 2020-11-05
_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.712
####################################################################### 
# 
# 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_GNPS-2
_database_code_depnum_ccdc_archive 'CCDC 2174350'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-28
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 O6 S2, C12 H22 O2, 2(C H6 N3)'
_chemical_formula_sum            'C24 H40 N6 O8 S2'
_chemical_formula_weight         604.74
_chemical_absolute_configuration unknown
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.5807(2)
_cell_length_b                   15.5281(3)
_cell_length_c                   21.0679(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3134.28(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4440
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.2870
_cell_measurement_theta_min      3.5070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8509
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.617
_diffrn_reflns_theta_min         3.536
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00   0.00   1.00    1.21    --  -40.73  77.00   0.00   32
  2  ω   -113.00 -15.00   1.00    1.21    --  -40.73 -57.00-180.00   98
  3  ω     41.00  82.00   1.00    1.21    --   40.73 -99.00-180.00   41
  4  ω     35.00  90.00   1.00    2.50    --  107.58-125.00-180.00   55
  5  ω     92.00 176.00   1.00    2.50    --  107.58  45.00 -90.00   84
  6  ω    110.00 174.00   1.00    2.50    --  107.58 125.00-180.00   64
  7  ω     85.00 170.00   1.00    2.50    --  107.58  45.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0591152000
_diffrn_orient_matrix_UB_12      0.0456129000
_diffrn_orient_matrix_UB_13      0.0591345000
_diffrn_orient_matrix_UB_21      -0.0445960000
_diffrn_orient_matrix_UB_22      0.0770511000
_diffrn_orient_matrix_UB_23      -0.0415576000
_diffrn_orient_matrix_UB_31      -0.1425084000
_diffrn_orient_matrix_UB_32      -0.0427221000
_diffrn_orient_matrix_UB_33      -0.0116918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.598
_reflns_Friedel_fraction_full    0.813
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                5019
_reflns_number_total             5576
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.033
_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)+(0.0481P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2C,H2D), N3(H3A,H3B), N4(H4C,H4D), N5(H5C,H5D), N6(H6A,H6B)
2.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.51933(9) 0.62370(4) 0.43023(3) 0.03345(18) Uani 1 1 d . . . . .
S2 S 0.46674(8) 0.63514(4) 0.10496(3) 0.02889(16) Uani 1 1 d . . . . .
O1 O 0.4048(3) 0.61773(15) 0.47525(10) 0.0421(6) Uani 1 1 d . . . . .
O2 O 0.6081(3) 0.54693(12) 0.43107(10) 0.0356(5) Uani 1 1 d . . . . .
O3 O 0.6013(3) 0.70233(12) 0.43790(11) 0.0396(6) Uani 1 1 d . . . . .
O4 O 0.3851(2) 0.55608(12) 0.10171(11) 0.0340(5) Uani 1 1 d . . . . .
O5 O 0.3783(2) 0.71150(12) 0.09943(10) 0.0322(5) Uani 1 1 d . . . . .
O6 O 0.5814(2) 0.63589(13) 0.05953(10) 0.0343(5) Uani 1 1 d . . . . .
O7 O -0.0494(2) 0.38977(14) 0.32543(10) 0.0381(5) Uani 1 1 d . . . . .
O8 O -0.0307(3) 0.52848(16) 0.35529(11) 0.0488(6) Uani 1 1 d . . . . .
C1 C -0.1505(3) 0.41122(19) 0.27612(13) 0.0301(6) Uani 1 1 d . . . . .
H1 H -0.139830 0.471987 0.264546 0.036 Uiso 1 1 calc R U . . .
C2 C -0.2963(3) 0.39684(19) 0.30226(15) 0.0335(7) Uani 1 1 d . . . . .
H2A H -0.312085 0.435672 0.337600 0.040 Uiso 1 1 calc R U . . .
H2B H -0.303851 0.338316 0.317999 0.040 Uiso 1 1 calc R U . . .
C3 C -0.4073(3) 0.41194(19) 0.25186(16) 0.0360(7) Uani 1 1 d . . . . .
H3 H -0.401510 0.472382 0.238729 0.043 Uiso 1 1 calc R U . . .
C4 C -0.3758(4) 0.3563(2) 0.19383(16) 0.0406(8) Uani 1 1 d . . . . .
H4A H -0.385562 0.296040 0.205248 0.049 Uiso 1 1 calc R U . . .
H4B H -0.443474 0.368785 0.160833 0.049 Uiso 1 1 calc R U . . .
C5 C -0.2296(3) 0.3716(2) 0.16809(15) 0.0388(7) Uani 1 1 d . . . . .
H5A H -0.222340 0.430503 0.153054 0.047 Uiso 1 1 calc R U . . .
H5B H -0.213216 0.333603 0.132331 0.047 Uiso 1 1 calc R U . . .
C6 C -0.1187(3) 0.35569(19) 0.21869(14) 0.0313(6) Uani 1 1 d . . . . .
H6 H -0.128775 0.295624 0.232214 0.038 Uiso 1 1 calc R U . . .
C7 C 0.0015(4) 0.4546(2) 0.36090(14) 0.0403(8) Uani 1 1 d . . . . .
C8 C 0.1072(4) 0.4209(3) 0.40726(17) 0.0585(11) Uani 1 1 d . . . . .
H8A H 0.063182 0.380616 0.435465 0.088 Uiso 1 1 calc R U . . .
H8B H 0.144989 0.467873 0.431359 0.088 Uiso 1 1 calc R U . . .
H8C H 0.181049 0.392548 0.384607 0.088 Uiso 1 1 calc R U . . .
C9 C -0.5549(4) 0.3962(2) 0.2776(2) 0.0512(10) Uani 1 1 d . . . . .
H9A H -0.563060 0.337391 0.291280 0.077 Uiso 1 1 calc R U . . .
H9B H -0.621961 0.407341 0.244790 0.077 Uiso 1 1 calc R U . . .
H9C H -0.571931 0.433841 0.312891 0.077 Uiso 1 1 calc R U . . .
C10 C 0.0339(4) 0.3665(2) 0.19478(15) 0.0403(7) Uani 1 1 d . . . . .
H10 H 0.095946 0.352314 0.230257 0.048 Uiso 1 1 calc R U . . .
C11 C 0.0674(5) 0.4579(3) 0.1744(2) 0.0602(11) Uani 1 1 d . . . . .
H11A H 0.006547 0.474390 0.140250 0.090 Uiso 1 1 calc R U . . .
H11B H 0.162575 0.460927 0.160349 0.090 Uiso 1 1 calc R U . . .
H11C H 0.054110 0.496270 0.209597 0.090 Uiso 1 1 calc R U . . .
C12 C 0.0663(5) 0.3030(3) 0.14070(18) 0.0539(10) Uani 1 1 d . . . . .
H12A H 0.040227 0.245896 0.153405 0.081 Uiso 1 1 calc R U . . .
H12B H 0.164344 0.304512 0.131391 0.081 Uiso 1 1 calc R U . . .
H12C H 0.014472 0.319120 0.103536 0.081 Uiso 1 1 calc R U . . .
C13 C 0.4434(3) 0.62719(17) 0.35332(14) 0.0289(6) Uani 1 1 d . . . . .
C14 C 0.3008(3) 0.62247(19) 0.34960(15) 0.0326(6) Uani 1 1 d . . . . .
H14 H 0.247796 0.618950 0.386473 0.039 Uiso 1 1 calc R U . . .
C15 C 0.2347(3) 0.62293(19) 0.28993(15) 0.0329(7) Uani 1 1 d . . . . .
H15 H 0.137877 0.619720 0.287606 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3114(3) 0.62806(18) 0.23545(14) 0.0294(6) Uani 1 1 d . . . . .
H16 H 0.266002 0.628166 0.196421 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4594(3) 0.63325(16) 0.23740(13) 0.0259(5) Uani 1 1 d . . . . .
C18 C 0.5281(3) 0.63365(16) 0.29763(13) 0.0272(5) Uani 1 1 d . . . . .
C19 C 0.6761(3) 0.63934(18) 0.29946(15) 0.0314(6) Uani 1 1 d . . . . .
H19 H 0.722102 0.638548 0.338330 0.038 Uiso 1 1 calc R U . . .
C20 C 0.7513(3) 0.6460(2) 0.24471(16) 0.0345(7) Uani 1 1 d . . . . .
H20 H 0.847877 0.650916 0.246897 0.041 Uiso 1 1 calc R U . . .
C21 C 0.6859(3) 0.64546(18) 0.18526(15) 0.0332(7) Uani 1 1 d . . . . .
H21 H 0.739012 0.649736 0.148442 0.040 Uiso 1 1 calc R U . . .
C22 C 0.5437(3) 0.63864(16) 0.18148(13) 0.0278(6) Uani 1 1 d . . . . .
C23 C 0.4160(3) 0.36772(19) 0.49708(14) 0.0321(6) Uani 1 1 d . . . . .
C24 C 0.9295(4) 0.61043(19) 0.51412(14) 0.0330(7) Uani 1 1 d . . . . .
N1 N 0.3719(3) 0.43908(16) 0.52555(13) 0.0374(6) Uani 1 1 d . . . . .
H1A H 0.405535 0.488241 0.514619 0.045 Uiso 1 1 calc R U . . .
H1B H 0.309703 0.436096 0.554901 0.045 Uiso 1 1 calc R U . . .
N2 N 0.3653(3) 0.29200(16) 0.51445(14) 0.0433(7) Uani 1 1 d . . . . .
H2C H 0.394544 0.245731 0.496374 0.052 Uiso 1 1 calc R U . . .
H2D H 0.303110 0.289077 0.543801 0.052 Uiso 1 1 calc R U . . .
N3 N 0.5113(3) 0.37254(16) 0.45213(12) 0.0402(6) Uani 1 1 d . . . . .
H3A H 0.540799 0.326390 0.433962 0.048 Uiso 1 1 calc R U . . .
H3B H 0.544079 0.421825 0.440958 0.048 Uiso 1 1 calc R U . . .
N4 N 0.8573(3) 0.53853(15) 0.50842(13) 0.0361(6) Uani 1 1 d . . . . .
H4C H 0.777330 0.539091 0.489894 0.043 Uiso 1 1 calc R U . . .
H4D H 0.890232 0.491083 0.523222 0.043 Uiso 1 1 calc R U . . .
N5 N 1.0531(3) 0.60946(17) 0.54243(14) 0.0419(7) Uani 1 1 d . . . . .
H5C H 1.100349 0.656295 0.545987 0.050 Uiso 1 1 calc R U . . .
H5D H 1.085963 0.562004 0.557224 0.050 Uiso 1 1 calc R U . . .
N6 N 0.8795(4) 0.68317(16) 0.49154(14) 0.0431(7) Uani 1 1 d . . . . .
H6A H 0.799540 0.683914 0.472992 0.052 Uiso 1 1 calc R U . . .
H6B H 0.926781 0.729967 0.495322 0.052 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 1.453(2) . ?
S1 O2 1.465(2) . ?
S1 O3 1.460(2) . ?
S1 C13 1.777(3) . ?
S2 O4 1.457(2) . ?
S2 O5 1.462(2) . ?
S2 O6 1.457(2) . ?
S2 C22 1.774(3) . ?
O7 C1 1.458(3) . ?
O7 C7 1.345(4) . ?
O8 C7 1.194(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.518(4) . ?
C1 C6 1.517(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.521(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.527(5) . ?
C3 C9 1.534(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.521(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.525(4) . ?
C6 H6 0.9800 . ?
C6 C10 1.556(4) . ?
C7 C8 1.501(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.517(5) . ?
C10 C12 1.538(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.370(4) . ?
C13 C18 1.430(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.408(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.421(4) . ?
C17 C18 1.430(4) . ?
C17 C22 1.431(4) . ?
C18 C19 1.421(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.400(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.369(4) . ?
C23 N1 1.329(4) . ?
C23 N2 1.324(4) . ?
C23 N3 1.318(4) . ?
C24 N4 1.319(4) . ?
C24 N5 1.326(4) . ?
C24 N6 1.316(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2C 0.8600 . ?
N2 H2D 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4C 0.8600 . ?
N4 H4D 0.8600 . ?
N5 H5C 0.8600 . ?
N5 H5D 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 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
O1 S1 O2 112.27(14) . . ?
O1 S1 O3 112.77(14) . . ?
O1 S1 C13 106.72(14) . . ?
O2 S1 C13 105.88(13) . . ?
O3 S1 O2 111.52(13) . . ?
O3 S1 C13 107.17(13) . . ?
O4 S2 O5 111.63(12) . . ?
O4 S2 O6 112.37(13) . . ?
O4 S2 C22 106.96(13) . . ?
O5 S2 C22 106.77(13) . . ?
O6 S2 O5 112.22(13) . . ?
O6 S2 C22 106.45(14) . . ?
C7 O7 C1 117.8(2) . . ?
O7 C1 H1 109.1 . . ?
O7 C1 C2 108.6(2) . . ?
O7 C1 C6 107.8(2) . . ?
C2 C1 H1 109.1 . . ?
C6 C1 H1 109.1 . . ?
C6 C1 C2 113.0(3) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 C3 111.6(3) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3 107.8 . . ?
C2 C3 C4 109.5(3) . . ?
C2 C3 C9 111.9(3) . . ?
C4 C3 H3 107.8 . . ?
C4 C3 C9 112.0(3) . . ?
C9 C3 H3 107.8 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 112.2(3) . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.5(3) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C1 C6 C5 109.0(3) . . ?
C1 C6 H6 106.8 . . ?
C1 C6 C10 112.7(3) . . ?
C5 C6 H6 106.8 . . ?
C5 C6 C10 114.3(2) . . ?
C10 C6 H6 106.8 . . ?
O7 C7 C8 110.2(3) . . ?
O8 C7 O7 124.8(3) . . ?
O8 C7 C8 125.0(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10 107.4 . . ?
C11 C10 C6 113.0(3) . . ?
C11 C10 H10 107.4 . . ?
C11 C10 C12 110.3(3) . . ?
C12 C10 C6 111.1(3) . . ?
C12 C10 H10 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 S1 117.3(2) . . ?
C14 C13 C18 121.5(3) . . ?
C18 C13 S1 121.2(2) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 C22 122.9(3) . . ?
C18 C17 C22 118.1(2) . . ?
C17 C18 C13 117.8(3) . . ?
C19 C18 C13 123.3(3) . . ?
C19 C18 C17 118.9(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 S2 120.8(2) . . ?
C21 C22 S2 118.0(2) . . ?
C21 C22 C17 121.2(3) . . ?
N2 C23 N1 119.9(3) . . ?
N3 C23 N1 119.8(3) . . ?
N3 C23 N2 120.2(3) . . ?
N4 C24 N5 120.0(3) . . ?
N6 C24 N4 120.2(3) . . ?
N6 C24 N5 119.8(3) . . ?
C23 N1 H1A 120.0 . . ?
C23 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C23 N2 H2C 120.0 . . ?
C23 N2 H2D 120.0 . . ?
H2C N2 H2D 120.0 . . ?
C23 N3 H3A 120.0 . . ?
C23 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C24 N4 H4C 120.0 . . ?
C24 N4 H4D 120.0 . . ?
H4C N4 H4D 120.0 . . ?
C24 N5 H5C 120.0 . . ?
C24 N5 H5D 120.0 . . ?
H5C N5 H5D 120.0 . . ?
C24 N6 H6A 120.0 . . ?
C24 N6 H6B 120.0 . . ?
H6A N6 H6B 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
S1 C13 C14 C15 -178.6(2) . . . . ?
S1 C13 C18 C17 177.98(18) . . . . ?
S1 C13 C18 C19 -1.2(4) . . . . ?
O1 S1 C13 C14 -1.1(3) . . . . ?
O1 S1 C13 C18 179.7(2) . . . . ?
O2 S1 C13 C14 118.7(2) . . . . ?
O2 S1 C13 C18 -60.6(3) . . . . ?
O3 S1 C13 C14 -122.1(2) . . . . ?
O3 S1 C13 C18 58.6(3) . . . . ?
O4 S2 C22 C17 -55.7(2) . . . . ?
O4 S2 C22 C21 123.4(2) . . . . ?
O5 S2 C22 C17 63.9(2) . . . . ?
O5 S2 C22 C21 -117.0(2) . . . . ?
O6 S2 C22 C17 -176.0(2) . . . . ?
O6 S2 C22 C21 3.1(3) . . . . ?
O7 C1 C2 C3 -176.0(2) . . . . ?
O7 C1 C6 C5 175.7(2) . . . . ?
O7 C1 C6 C10 -56.4(3) . . . . ?
C1 O7 C7 O8 0.6(5) . . . . ?
C1 O7 C7 C8 -178.0(3) . . . . ?
C1 C2 C3 C4 54.3(3) . . . . ?
C1 C2 C3 C9 179.1(3) . . . . ?
C1 C6 C10 C11 -60.8(4) . . . . ?
C1 C6 C10 C12 174.6(3) . . . . ?
C2 C1 C6 C5 55.7(3) . . . . ?
C2 C1 C6 C10 -176.4(2) . . . . ?
C2 C3 C4 C5 -55.3(3) . . . . ?
C3 C4 C5 C6 57.0(4) . . . . ?
C4 C5 C6 C1 -55.4(3) . . . . ?
C4 C5 C6 C10 177.6(3) . . . . ?
C5 C6 C10 C11 64.3(4) . . . . ?
C5 C6 C10 C12 -60.3(4) . . . . ?
C6 C1 C2 C3 -56.5(3) . . . . ?
C7 O7 C1 C2 -96.4(3) . . . . ?
C7 O7 C1 C6 140.9(3) . . . . ?
C9 C3 C4 C5 -180.0(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C13 C18 C19 C20 -179.6(3) . . . . ?
C14 C13 C18 C17 -1.3(4) . . . . ?
C14 C13 C18 C19 179.5(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C17 C22 179.9(3) . . . . ?
C16 C17 C18 C13 1.1(4) . . . . ?
C16 C17 C18 C19 -179.6(3) . . . . ?
C16 C17 C22 S2 -2.3(4) . . . . ?
C16 C17 C22 C21 178.6(3) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
C18 C13 C14 C15 0.7(5) . . . . ?
C18 C17 C22 S2 178.02(19) . . . . ?
C18 C17 C22 C21 -1.1(4) . . . . ?
C18 C19 C20 C21 -1.4(5) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 S2 -178.2(2) . . . . ?
C20 C21 C22 C17 0.9(4) . . . . ?
C22 C17 C18 C13 -179.3(2) . . . . ?
C22 C17 C18 C19 0.0(4) . . . . ?

_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 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.668
