# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2020

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1999205'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-04-25 deposited with the CCDC.	2020-09-11 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 N4 O3 S2, C7 H7 N1 O2'
_chemical_formula_sum            'C11 H13 N5 O5 S2'
_chemical_formula_weight         359.38

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.8618(14)
_cell_length_b                   7.5904(4)
_cell_length_c                   14.3121(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.3061(7)
_cell_angle_gamma                90.00
_cell_volume                     3038.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9180
_cell_measurement_theta_min      2.781
_cell_measurement_theta_max      30.517

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8934
_exptl_absorpt_correction_T_max  0.9271
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17639
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4430
_reflns_number_gt                3927
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0464P)²+1.9752P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4430
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.30856(4) 0.81591(15) 0.42553(8) 0.0263(2) Uani 1 1 d . . .
H1 H 0.3065(7) 0.908(2) 0.4598(13) 0.039(5) Uiso 1 1 d . . .
H2 H 0.2910(6) 0.724(2) 0.4326(12) 0.036(4) Uiso 1 1 d . . .
O1 O 0.52750(3) 0.77040(13) 0.42130(9) 0.0368(2) Uani 1 1 d . . .
H10 H 0.5544(8) 0.734(3) 0.4173(15) 0.061(6) Uiso 1 1 d . . .
O2 O 0.50621(3) 0.49306(12) 0.37568(7) 0.0299(2) Uani 1 1 d . . .
C1 C 0.49608(4) 0.63953(16) 0.40041(9) 0.0245(2) Uani 1 1 d . . .
C2 C 0.44785(4) 0.68737(16) 0.41016(8) 0.0212(2) Uani 1 1 d . . .
C3 C 0.43645(4) 0.85936(16) 0.43142(9) 0.0244(2) Uani 1 1 d . . .
C4 C 0.39074(4) 0.90121(16) 0.43790(9) 0.0253(2) Uani 1 1 d . . .
C5 C 0.35522(4) 0.77117(16) 0.42432(8) 0.0210(2) Uani 1 1 d . . .
C6 C 0.36685(4) 0.59823(16) 0.40460(8) 0.0217(2) Uani 1 1 d . . .
C7 C 0.41263(4) 0.55748(16) 0.39754(8) 0.0217(2) Uani 1 1 d . . .
H3 H 0.4582(6) 0.950(2) 0.4408(12) 0.034(4) Uiso 1 1 d . . .
H4 H 0.3820(6) 1.021(2) 0.4527(13) 0.037(4) Uiso 1 1 d . . .
H6 H 0.3426(6) 0.513(2) 0.3942(12) 0.035(4) Uiso 1 1 d . . .
H7 H 0.4201(6) 0.441(2) 0.3826(11) 0.030(4) Uiso 1 1 d . . .
S1 S 0.683027(9) 0.52589(4) 0.33979(2) 0.02151(8) Uani 1 1 d . . .
S2 S 0.737206(9) 0.87470(4) 0.371562(19) 0.01965(7) Uani 1 1 d . . .
N11 N 0.65062(4) 0.80785(14) 0.40170(8) 0.0255(2) Uani 1 1 d . . .
N12 N 0.61484(4) 0.68480(14) 0.39195(8) 0.0260(2) Uani 1 1 d . . .
N13 N 0.59507(4) 0.39558(14) 0.34294(7) 0.0234(2) Uani 1 1 d . . .
H13 H 0.5662(7) 0.414(3) 0.3525(14) 0.050(5) Uiso 1 1 d . . .
N14 N 0.72341(4) 0.97995(15) 0.27236(8) 0.0252(2) Uani 1 1 d . . .
H11 H 0.7005(7) 1.061(3) 0.2693(13) 0.045(5) Uiso 1 1 d . . .
H12 H 0.7192(6) 0.918(3) 0.2195(13) 0.039(5) Uiso 1 1 d . . .
O11 O 0.74303(3) 1.00126(12) 0.44789(6) 0.02786(19) Uani 1 1 d . . .
O12 O 0.77501(3) 0.75475(12) 0.36923(7) 0.02742(19) Uani 1 1 d . . .
O13 O 0.64451(3) 0.21605(13) 0.28842(8) 0.0326(2) Uani 1 1 d . . .
C11 C 0.68750(4) 0.74266(15) 0.37732(8) 0.0210(2) Uani 1 1 d . . .
C12 C 0.62652(4) 0.53327(15) 0.35954(8) 0.0210(2) Uani 1 1 d . . .
C13 C 0.60553(4) 0.23860(16) 0.30554(9) 0.0244(2) Uani 1 1 d . . .
C14 C 0.56592(5) 0.1063(2) 0.28609(12) 0.0340(3) Uani 1 1 d . . .
H141 H 0.5407(8) 0.149(3) 0.2331(16) 0.060(6) Uiso 1 1 d . . .
H142 H 0.5507(9) 0.096(3) 0.3354(17) 0.070(7) Uiso 1 1 d . . .
H143 H 0.5786(8) -0.005(3) 0.2706(16) 0.061(6) 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
N1 C5 1.3932(14) . ?
N1 H1 0.863(19) . ?
N1 H2 0.881(19) . ?
O1 C1 1.3284(15) . ?
O1 H10 0.84(2) . ?
O2 C1 1.2239(15) . ?
C1 C2 1.4781(15) . ?
C2 C7 1.3955(16) . ?
C2 C3 1.3981(17) . ?
C3 C4 1.3822(16) . ?
C3 H3 0.916(18) . ?
C4 C5 1.4015(16) . ?
C4 H4 0.982(18) . ?
C5 C6 1.4007(16) . ?
C6 C7 1.3849(15) . ?
C6 H6 0.936(17) . ?
C7 H7 0.948(17) . ?
S1 C12 1.7234(11) . ?
S1 C11 1.7257(12) . ?
S2 O12 1.4278(9) . ?
S2 O11 1.4331(9) . ?
S2 N14 1.5916(11) . ?
S2 C11 1.7685(11) . ?
N11 C11 1.2974(14) . ?
N11 N12 1.3738(14) . ?
N12 C12 1.3150(15) . ?
N13 C12 1.3660(15) . ?
N13 C13 1.3701(16) . ?
N13 H13 0.89(2) . ?
N14 H11 0.90(2) . ?
N14 H12 0.874(19) . ?
O13 C13 1.2212(15) . ?
C13 C14 1.4951(17) . ?
C14 H141 0.97(2) . ?
C14 H142 0.92(3) . ?
C14 H143 0.97(2) . ?

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
C5 N1 H1 114.0(12) . . ?
C5 N1 H2 113.2(11) . . ?
H1 N1 H2 116.9(17) . . ?
C1 O1 H10 109.2(16) . . ?
O2 C1 O1 123.08(11) . . ?
O2 C1 C2 123.25(11) . . ?
O1 C1 C2 113.67(11) . . ?
C7 C2 C3 118.99(10) . . ?
C7 C2 C1 119.15(11) . . ?
C3 C2 C1 121.86(10) . . ?
C4 C3 C2 120.61(11) . . ?
C4 C3 H3 116.7(11) . . ?
C2 C3 H3 122.7(11) . . ?
C3 C4 C5 120.42(11) . . ?
C3 C4 H4 121.8(11) . . ?
C5 C4 H4 117.8(11) . . ?
N1 C5 C6 120.75(11) . . ?
N1 C5 C4 120.18(11) . . ?
C6 C5 C4 118.98(10) . . ?
C7 C6 C5 120.29(10) . . ?
C7 C6 H6 121.6(11) . . ?
C5 C6 H6 118.1(11) . . ?
C6 C7 C2 120.70(11) . . ?
C6 C7 H7 119.9(10) . . ?
C2 C7 H7 119.4(10) . . ?
C12 S1 C11 85.36(6) . . ?
O12 S2 O11 119.93(6) . . ?
O12 S2 N14 108.86(6) . . ?
O11 S2 N14 107.45(6) . . ?
O12 S2 C11 105.85(6) . . ?
O11 S2 C11 106.74(5) . . ?
N14 S2 C11 107.40(5) . . ?
C11 N11 N12 111.07(10) . . ?
C12 N12 N11 112.25(9) . . ?
C12 N13 C13 122.16(10) . . ?
C12 N13 H13 117.4(13) . . ?
C13 N13 H13 120.2(13) . . ?
S2 N14 H11 114.0(12) . . ?
S2 N14 H12 117.0(12) . . ?
H11 N14 H12 112.5(16) . . ?
N11 C11 S1 116.36(9) . . ?
N11 C11 S2 121.69(9) . . ?
S1 C11 S2 121.67(6) . . ?
N12 C12 N13 120.88(10) . . ?
N12 C12 S1 114.95(8) . . ?
N13 C12 S1 124.17(9) . . ?
O13 C13 N13 120.21(11) . . ?
O13 C13 C14 124.65(12) . . ?
N13 C13 C14 115.12(11) . . ?
C13 C14 H141 108.5(13) . . ?
C13 C14 H142 113.7(15) . . ?
H141 C14 H142 102.7(19) . . ?
C13 C14 H143 108.2(13) . . ?
H141 C14 H143 111.3(18) . . ?
H142 C14 H143 112(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
O2 C1 C2 C7 4.77(18) . . . . ?
O1 C1 C2 C7 -175.04(11) . . . . ?
O2 C1 C2 C3 -175.04(12) . . . . ?
O1 C1 C2 C3 5.14(17) . . . . ?
C7 C2 C3 C4 -1.33(18) . . . . ?
C1 C2 C3 C4 178.49(11) . . . . ?
C2 C3 C4 C5 0.73(19) . . . . ?
C3 C4 C5 N1 -176.36(11) . . . . ?
C3 C4 C5 C6 0.33(18) . . . . ?
N1 C5 C6 C7 175.90(11) . . . . ?
C4 C5 C6 C7 -0.77(17) . . . . ?
C5 C6 C7 C2 0.17(17) . . . . ?
C3 C2 C7 C6 0.88(17) . . . . ?
C1 C2 C7 C6 -178.94(11) . . . . ?
C11 N11 N12 C12 -0.72(15) . . . . ?
N12 N11 C11 S1 0.10(14) . . . . ?
N12 N11 C11 S2 174.09(8) . . . . ?
C12 S1 C11 N11 0.39(10) . . . . ?
C12 S1 C11 S2 -173.61(8) . . . . ?
O12 S2 C11 N11 164.44(10) . . . . ?
O11 S2 C11 N11 35.61(12) . . . . ?
N14 S2 C11 N11 -79.38(11) . . . . ?
O12 S2 C11 S1 -21.88(9) . . . . ?
O11 S2 C11 S1 -150.71(7) . . . . ?
N14 S2 C11 S1 94.30(8) . . . . ?
N11 N12 C12 N13 -178.45(10) . . . . ?
N11 N12 C12 S1 1.05(14) . . . . ?
C13 N13 C12 N12 177.32(11) . . . . ?
C13 N13 C12 S1 -2.14(17) . . . . ?
C11 S1 C12 N12 -0.81(10) . . . . ?
C11 S1 C12 N13 178.67(11) . . . . ?
C12 N13 C13 O13 2.12(18) . . . . ?
C12 N13 C13 C14 -176.24(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H10 N12 0.84(2) 1.90(2) 2.7341(14) 170(2) .
N13 H13 O2 0.89(2) 1.94(2) 2.8177(13) 171.0(19) .
N1 H1 O11 0.863(19) 2.281(19) 2.9594(13) 135.6(16) 5_676
N1 H2 O11 0.881(19) 2.232(19) 3.1117(14) 176.8(16) 3_445
N14 H11 O13 0.90(2) 2.07(2) 2.9511(14) 166.9(17) 1_565
N14 H12 N1 0.874(19) 2.174(19) 3.0219(16) 163.4(17) 2_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.052
