data_global
_audit_creation_method                  'APEX4 v2022.1-1'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;

Brandenburg, K. (2014) "Diamond 3.2k4", Crystal Impact GbR: Bonn Germany.

Bruker (2020). APEX4. Bruker AXS LLC, Madison, WI, USA.

Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011).
"ShelXle: a Qt graphical user interface for SHELXL",
J. Appl. Cryst. 44, 1281--1284.
doi:10.1107/S0021889811043202

Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.;
Taylor, R.; Towler, M.; van de Streek, J. (2006),
"Mercury: visualization and analysis of crystal structures"
Journal of Applied Crystallography 39 (3), 453--457.
doi: 10.1107/S002188980600731X

Sheldrick, G. M. (2015). "SHELXT--Integrated space--group and
crystal--structure determination",
Acta Cryst. A71, 3--8.
doi:10.1107/S2053273314026370

Sheldrick, G. M. (2015) "Crystal structure refinement with SHELXL",
Acta Cryst., C71, 3--8
doi:10.1107/S2053229614024218

Spek, A. L. (2009). "Structure validation in chemical crystallography",
Acta Cryst. D65, 148--155.
doi:10.1107/S090744490804362X

Wilson, A. J. C. (Ed). (1992)
International Tables for Crystallography,  Volume C.
Kluwer Academic Publishers, Dordrecht: Tables 6.1.1.4 (pp. 500--502),
4.2.6.8 (pp. 219--222) and 4.2.4.2 (pp. 193--199).
doi: 10.1107/97809553602060000103
;
_publ_section_comment                   
;
;

data_23mdw35ay
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C12 H18 N6 O6 S2'
_chemical_formula_iupac                 ?
_chemical_formula_weight                406.44

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_IT_number                  14
_space_group_name_H-M_alt               'P 1 21/c 1'
_space_group_name_Hall                  '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'

_cell_length_a                          11.359(5)
_cell_length_b                          9.285(4)
_cell_length_c                          9.048(4)
_cell_angle_alpha                       90
_cell_angle_beta                        101.453(12)
_cell_angle_gamma                       90
_cell_volume                            935.3(8)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           1261
_cell_measurement_theta_min             3.1766
_cell_measurement_theta_max             20.8004
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.886
_exptl_crystal_size_mid                 0.471
_exptl_crystal_size_min                 0.190
_exptl_crystal_density_diffrn           1.443
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    424

_exptl_absorpt_coefficient_mu           0.326
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min         0.75
_exptl_absorpt_correction_T_max         0.94

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             100.(2)

_diffrn_source                          'microfocus sealed X-ray tube'
_diffrn_source_type                     Incoatec
_diffrn_source_power                    0.05
_diffrn_source_current                  1.0
_diffrn_source_voltage                  50

_diffrn_radiation_probe                 x-ray
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         'multilayer optics'

_diffrn_measurement_device              'three-circle diffractometer'
_diffrn_measurement_device_type         'Bruker D8 SMART APEXII'
_diffrn_measurement_method              'φ and ω scans'

_diffrn_detector_area_resol_mean        7.3910

_diffrn_reflns_number                   2443
_diffrn_reflns_av_R_equivalents         0.0589
_diffrn_reflns_av_unetI/netI            0.0593
_diffrn_reflns_theta_min                2.86
_diffrn_reflns_theta_max                20.91
_diffrn_reflns_theta_full               20.91
_diffrn_measured_fraction_theta_max     0.780
_diffrn_measured_fraction_theta_full    0.780
_diffrn_reflns_limit_h_min              -11
_diffrn_reflns_limit_h_max              11
_diffrn_reflns_limit_k_min              -6
_diffrn_reflns_limit_k_max              6
_diffrn_reflns_limit_l_min              -8
_diffrn_reflns_limit_l_max              9

_refine_special_details                 
;
;

_reflns_number_total                    772
_reflns_number_gt                       640
_reflns_threshold_expression            'I > 2σ(I)'
_reflns_Friedel_coverage                0.000
_reflns_Friedel_fraction_max            .
_reflns_Friedel_fraction_full           .

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.1106
_refine_ls_R_factor_gt                  0.0953
_refine_ls_wR_factor_gt                 0.2229
_refine_ls_wR_factor_ref                0.2300
_refine_ls_goodness_of_fit_ref          1.386
_refine_ls_restrained_S_all             1.386
_refine_ls_number_reflns                772
_refine_ls_number_parameters            118
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0206P)²+12.5738P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            dual
_atom_sites_solution_secondary          difmap

_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.445
_refine_diff_density_min                -0.382
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              'Bruker APEX4'
_computing_cell_refinement              'Bruker APEX4'
_computing_data_reduction               'Bruker APEX4'
_computing_structure_solution           'SHELXT (Sheldrick 2015)'
_computing_structure_refinement         'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics           'Diamond (Brakdenburg 2014)'
_computing_publication_material         'Bruker APEX4'

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.1929(2) 0.5473(5) 0.4190(4) 0.0236(14) Uani d . . . 1 . .
    O O1 0.1856(6) 0.5930(11) 0.2637(9) 0.026(3) Uani d . . . 1 . .
    O O2 0.1632(6) 0.3933(13) 0.4294(9) 0.024(3) Uani d . . . 1 . .
    O O3 0.1245(6) 0.6388(12) 0.5016(9) 0.028(3) Uani d . . . 1 . .
    N N1 0.1178(7) 0.1386(16) 0.2475(12) 0.030(4) Uani d . . . 1 . .
    H H1A 0.129367 0.230945 0.266829 0.036000 Uiso calc U . R 1 . .
    H H1B 0.102248 0.107959 0.153598 0.036000 Uiso calc U . R 1 . .
    N N2 0.1465(8) 0.0865(15) 0.4976(13) 0.031(4) Uani d . . . 1 . .
    H H2A 0.158289 0.178325 0.519469 0.038000 Uiso calc U . R 1 . .
    H H2B 0.150129 0.022814 0.570430 0.038000 Uiso calc U . R 1 . .
    N N3 0.1094(8) -0.0940(19) 0.3221(13) 0.032(4) Uani d . . . 1 . .
    H H3A 0.115191 -0.160135 0.392860 0.039000 Uiso calc U . R 1 . .
    H H3B 0.093951 -0.119388 0.226481 0.039000 Uiso calc U . R 1 . .
    C C1 0.3467(9) 0.5725(17) 0.5111(14) 0.022(4) Uani d . . . 1 . .
    C C2 0.3714(10) 0.6647(19) 0.6286(15) 0.033(5) Uani d . . . 1 . .
    H H2C 0.307836 0.713623 0.661653 0.039000 Uiso calc U . R 1 . .
    C C3 0.4920(10) 0.689(2) 0.7028(14) 0.039(6) Uani d . . . 1 . .
    H H3 0.509971 0.756588 0.782603 0.047000 Uiso calc U . R 1 . .
    C C4 0.5826(10) 0.612(2) 0.6580(15) 0.037(5) Uani d . . . 1 . .
    H H4 0.662960 0.626753 0.710060 0.044000 Uiso calc U . R 1 . .
    C C5 0.5608(10) 0.5136(18) 0.5382(14) 0.026(5) Uani d . . . 1 . .
    C C6 0.1240(10) 0.045(3) 0.3600(16) 0.032(5) Uani d . . . 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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . 1.454(9) ?
    S1 O3 . 1.454(10) ?
    S1 O2 . 1.477(11) ?
    S1 C1 . 1.795(11) ?
    N1 C6 . 1.33(2) ?
    N1 H1A . 0.880000 ?
    N1 H1B . 0.880000 ?
    N2 C6 . 1.278(18) ?
    N2 H2A . 0.880000 ?
    N2 H2B . 0.880000 ?
    N3 C6 . 1.34(2) ?
    N3 H3A . 0.880000 ?
    N3 H3B . 0.880000 ?
    C1 C2 . 1.350(19) ?
    C1 C5 3_666 1.459(18) ?
    C2 C3 . 1.418(17) ?
    C2 H2C . 0.950000 ?
    C3 C4 . 1.376(19) ?
    C3 H3 . 0.950000 ?
    C4 C5 . 1.40(2) ?
    C4 H4 . 0.950000 ?
    C5 C5 3_666 1.44(2) ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O3 . . 113.1(6) ?
    O1 S1 O2 . . 111.9(5) ?
    O3 S1 O2 . . 112.4(5) ?
    O1 S1 C1 . . 105.9(5) ?
    O3 S1 C1 . . 104.8(6) ?
    O2 S1 C1 . . 108.1(6) ?
    C6 N1 H1A . . 120.000000 ?
    C6 N1 H1B . . 120.000000 ?
    H1A N1 H1B . . 120.000000 ?
    C6 N2 H2A . . 120.000000 ?
    C6 N2 H2B . . 120.000000 ?
    H2A N2 H2B . . 120.000000 ?
    C6 N3 H3A . . 120.000000 ?
    C6 N3 H3B . . 120.000000 ?
    H3A N3 H3B . . 120.000000 ?
    C2 C1 C5 . 3_666 122.6(11) ?
    C2 C1 S1 . . 118.6(9) ?
    C5 C1 S1 3_666 . 118.7(10) ?
    C1 C2 C3 . . 120.1(12) ?
    C1 C2 H2C . . 119.900000 ?
    C3 C2 H2C . . 119.900000 ?
    C4 C3 C2 . . 119.2(13) ?
    C4 C3 H3 . . 120.400000 ?
    C2 C3 H3 . . 120.400000 ?
    C3 C4 C5 . . 122.4(11) ?
    C3 C4 H4 . . 118.800000 ?
    C5 C4 H4 . . 118.800000 ?
    C4 C5 C5 . 3_666 119.5(15) ?
    C4 C5 C1 . 3_666 124.5(11) ?
    C5 C5 C1 3_666 3_666 115.9(17) ?
    N2 C6 N1 . . 122.(2) ?
    N2 C6 N3 . . 121.8(16) ?
    N1 C6 N3 . . 116.6(14) ?



