# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_exp_1520
_database_code_depnum_ccdc_archive 'CCDC 2401392'
loop_
_audit_author_name
_audit_author_address
'Slepukhin P.A.'
;iOS UB RAS
Russia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-09-18
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H14 N8 S'
_chemical_formula_sum            'C11 H14 N8 S'
_chemical_formula_weight         290.36
_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 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   13.0522(13)
_cell_length_b                   7.5876(12)
_cell_length_c                   28.440(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2816.5(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1671
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.2590
_cell_measurement_theta_min      2.8560
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            11951
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.86
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9877
_diffrn_measured_fraction_theta_max 0.9184
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  91.00   1.00  100.00    --   21.40  38.00 -90.00   85
  2  ω     -7.00  93.00   1.00  100.00    --   21.40  19.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0169019000
_diffrn_orient_matrix_UB_12      0.0157409000
_diffrn_orient_matrix_UB_13      -0.0233674000
_diffrn_orient_matrix_UB_21      -0.0173273000
_diffrn_orient_matrix_UB_22      -0.0848417000
_diffrn_orient_matrix_UB_23      -0.0066533000
_diffrn_orient_matrix_UB_31      -0.0486884000
_diffrn_orient_matrix_UB_32      0.0356473000
_diffrn_orient_matrix_UB_33      -0.0057123000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1446
_reflns_number_total             3957
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0026(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1891
_refine_ls_R_factor_gt           0.0828
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0980P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2670
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
S1 S 0.46871(9) 0.9162(2) 0.57690(5) 0.1017(6) Uani 1 1 d . . .
N1 N 0.34140(19) 0.6759(4) 0.67582(10) 0.0574(8) Uani 1 1 d . . .
N2 N 0.4274(2) 0.7288(4) 0.65283(11) 0.0685(9) Uani 1 1 d . . .
N3 N 0.1303(2) 0.4519(4) 0.79568(10) 0.0651(9) Uani 1 1 d . . .
H3 H 0.0774 0.4890 0.7806 0.078 Uiso 1 1 calc R . .
N4 N 0.2831(2) 0.8268(5) 0.61507(11) 0.0684(9) Uani 1 1 d . . .
N6 N 0.1584(2) 0.7045(5) 0.66846(11) 0.0660(9) Uani 1 1 d . . .
N7 N 0.1494(2) 0.6183(4) 0.70799(11) 0.0633(8) Uani 1 1 d . . .
N10 N 0.3054(2) 0.4131(4) 0.79937(10) 0.0647(8) Uani 1 1 d . . .
N12 N 0.4173(2) 0.5316(4) 0.73981(11) 0.0636(9) Uani 1 1 d . . .
C3 C 0.3863(3) 0.8187(6) 0.61650(13) 0.0717(11) Uani 1 1 d . . .
C5 C 0.2559(3) 0.7361(6) 0.65291(13) 0.0615(10) Uani 1 1 d . . .
C8 C 0.2333(2) 0.5606(5) 0.73208(12) 0.0571(9) Uani 1 1 d . . .
C9 C 0.2209(3) 0.4757(5) 0.77622(13) 0.0592(9) Uani 1 1 d . . .
C11 C 0.3958(3) 0.4443(6) 0.77960(14) 0.0667(11) Uani 1 1 d . . .
H11 H 0.4521 0.3992 0.7956 0.080 Uiso 1 1 calc R . .
C13 C 0.3343(2) 0.5863(5) 0.71723(13) 0.0574(9) Uani 1 1 d . . .
C14 C 0.3809(4) 1.0418(8) 0.54320(18) 0.127(2) Uani 1 1 d . . .
H14A H 0.4171 1.1034 0.5188 0.190 Uiso 1 1 calc R . .
H14B H 0.3470 1.1254 0.5632 0.190 Uiso 1 1 calc R . .
H14C H 0.3310 0.9648 0.5293 0.190 Uiso 1 1 calc R . .
C15 C 0.1139(3) 0.3678(6) 0.84056(14) 0.0749(12) Uani 1 1 d . . .
H15A H 0.1535 0.2597 0.8415 0.090 Uiso 1 1 calc R . .
H15B H 0.0421 0.3358 0.8431 0.090 Uiso 1 1 calc R . .
C16 C 0.1421(3) 0.4780(7) 0.88229(14) 0.0882(14) Uani 1 1 d . . .
H16A H 0.2154 0.4984 0.8821 0.106 Uiso 1 1 calc R . .
H16B H 0.1084 0.5916 0.8798 0.106 Uiso 1 1 calc R . .
C17 C 0.1126(6) 0.3938(9) 0.9279(2) 0.134(2) Uani 1 1 d . . .
H17A H 0.0385 0.3849 0.9287 0.161 Uiso 1 1 calc R . .
H17B H 0.1395 0.2746 0.9279 0.161 Uiso 1 1 calc R . .
C18 C 0.1446(7) 0.4765(14) 0.9694(3) 0.205(4) Uani 1 1 d . . .
H18A H 0.2177 0.4663 0.9724 0.308 Uiso 1 1 calc R . .
H18B H 0.1123 0.4210 0.9959 0.308 Uiso 1 1 calc R . .
H18C H 0.1259 0.5988 0.9685 0.308 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0804(9) 0.1160(12) 0.1087(11) 0.0181(8) 0.0229(6) -0.0023(7)
N1 0.0358(15) 0.064(2) 0.0727(19) -0.0103(15) -0.0021(13) -0.0011(13)
N2 0.0462(17) 0.077(2) 0.083(2) -0.0066(16) 0.0085(16) -0.0073(16)
N3 0.0347(14) 0.080(2) 0.081(2) -0.0030(17) -0.0020(14) 0.0018(14)
N4 0.0558(19) 0.077(2) 0.073(2) -0.0035(17) -0.0021(15) 0.0004(16)
N6 0.0397(17) 0.079(2) 0.080(2) -0.0066(17) -0.0049(14) 0.0069(15)
N7 0.0356(15) 0.077(2) 0.077(2) -0.0060(16) -0.0045(14) 0.0055(14)
N10 0.0399(15) 0.072(2) 0.082(2) -0.0024(16) -0.0046(14) 0.0048(15)
N12 0.0352(15) 0.076(2) 0.080(2) -0.0043(16) -0.0054(14) 0.0062(14)
C3 0.061(2) 0.078(3) 0.076(3) -0.010(2) 0.004(2) -0.002(2)
C5 0.0415(19) 0.074(3) 0.069(2) -0.0130(19) -0.0052(17) 0.0069(17)
C8 0.0323(17) 0.063(2) 0.076(2) -0.0123(18) -0.0064(15) 0.0032(15)
C9 0.0383(17) 0.064(2) 0.076(2) -0.0092(19) -0.0029(16) -0.0005(16)
C11 0.0372(19) 0.076(3) 0.087(3) -0.005(2) -0.0088(18) 0.0114(18)
C13 0.0415(18) 0.062(2) 0.069(2) -0.0129(18) -0.0036(16) 0.0028(16)
C14 0.133(5) 0.147(6) 0.100(4) 0.030(3) 0.026(3) 0.022(4)
C15 0.050(2) 0.088(3) 0.087(3) 0.006(2) 0.0047(19) -0.001(2)
C16 0.070(3) 0.108(4) 0.086(3) 0.001(3) 0.000(2) 0.007(3)
C17 0.139(5) 0.166(7) 0.096(4) 0.001(4) 0.009(4) -0.007(5)
C18 0.212(9) 0.277(13) 0.126(6) -0.002(6) -0.014(6) -0.029(8)

_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 C3 1.724(4) . ?
S1 C14 1.772(6) . ?
N1 N2 1.360(4) . ?
N1 C5 1.371(4) . ?
N1 C13 1.363(5) . ?
N2 C3 1.349(5) . ?
N3 H3 0.8600 . ?
N3 C9 1.317(4) . ?
N3 C15 1.443(5) . ?
N4 C3 1.349(5) . ?
N4 C5 1.326(5) . ?
N6 N7 1.306(4) . ?
N6 C5 1.369(4) . ?
N7 C8 1.364(4) . ?
N10 C9 1.370(4) . ?
N10 C11 1.328(4) . ?
N12 C11 1.341(5) . ?
N12 C13 1.327(4) . ?
C8 C9 1.420(5) . ?
C8 C13 1.398(4) . ?
C11 H11 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.498(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.495(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.401(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C3 S1 C14 100.4(2) . . ?
N2 N1 C5 110.2(3) . . ?
N2 N1 C13 128.3(3) . . ?
C13 N1 C5 121.4(3) . . ?
C3 N2 N1 100.9(3) . . ?
C9 N3 H3 117.8 . . ?
C9 N3 C15 124.4(3) . . ?
C15 N3 H3 117.8 . . ?
C5 N4 C3 102.7(3) . . ?
N7 N6 C5 116.7(3) . . ?
N6 N7 C8 121.4(3) . . ?
C11 N10 C9 116.8(3) . . ?
C13 N12 C11 113.0(3) . . ?
N2 C3 S1 118.0(3) . . ?
N4 C3 S1 125.7(3) . . ?
N4 C3 N2 116.3(3) . . ?
N4 C5 N1 109.9(3) . . ?
N4 C5 N6 127.0(3) . . ?
N6 C5 N1 123.0(4) . . ?
N7 C8 C9 119.9(3) . . ?
N7 C8 C13 124.1(4) . . ?
C13 C8 C9 116.0(3) . . ?
N3 C9 N10 118.2(3) . . ?
N3 C9 C8 122.4(3) . . ?
N10 C9 C8 119.3(3) . . ?
N10 C11 N12 129.2(3) . . ?
N10 C11 H11 115.4 . . ?
N12 C11 H11 115.4 . . ?
N1 C13 C8 113.3(3) . . ?
N12 C13 N1 121.2(3) . . ?
N12 C13 C8 125.5(4) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 108.6 . . ?
N3 C15 H15B 108.6 . . ?
N3 C15 C16 114.7(4) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 112.6(5) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 107.9 . . ?
C16 C17 H17B 107.9 . . ?
H17A C17 H17B 107.2 . . ?
C18 C17 C16 117.6(7) . . ?
C18 C17 H17A 107.9 . . ?
C18 C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
N1 N2 C3 S1 179.1(3) . . . . ?
N1 N2 C3 N4 0.3(4) . . . . ?
N2 N1 C5 N4 0.4(4) . . . . ?
N2 N1 C5 N6 -179.2(3) . . . . ?
N2 N1 C13 N12 -3.1(6) . . . . ?
N2 N1 C13 C8 177.0(3) . . . . ?
N3 C15 C16 C17 173.4(4) . . . . ?
N6 N7 C8 C9 176.6(3) . . . . ?
N6 N7 C8 C13 -0.3(6) . . . . ?
N7 N6 C5 N1 2.7(6) . . . . ?
N7 N6 C5 N4 -176.9(4) . . . . ?
N7 C8 C9 N3 -1.0(6) . . . . ?
N7 C8 C9 N10 177.8(3) . . . . ?
N7 C8 C13 N1 0.0(5) . . . . ?
N7 C8 C13 N12 -179.9(3) . . . . ?
C3 N4 C5 N1 -0.2(4) . . . . ?
C3 N4 C5 N6 179.4(4) . . . . ?
C5 N1 N2 C3 -0.4(4) . . . . ?
C5 N1 C13 N12 -178.5(3) . . . . ?
C5 N1 C13 C8 1.6(5) . . . . ?
C5 N4 C3 S1 -178.7(3) . . . . ?
C5 N4 C3 N2 -0.1(5) . . . . ?
C5 N6 N7 C8 -1.0(5) . . . . ?
C9 N3 C15 C16 74.5(5) . . . . ?
C9 N10 C11 N12 0.9(6) . . . . ?
C9 C8 C13 N1 -177.0(3) . . . . ?
C9 C8 C13 N12 3.1(5) . . . . ?
C11 N10 C9 N3 -177.9(3) . . . . ?
C11 N10 C9 C8 3.3(5) . . . . ?
C11 N12 C13 N1 -179.3(3) . . . . ?
C11 N12 C13 C8 0.6(5) . . . . ?
C13 N1 N2 C3 -176.2(4) . . . . ?
C13 N1 C5 N4 176.6(3) . . . . ?
C13 N1 C5 N6 -3.1(6) . . . . ?
C13 N12 C11 N10 -2.9(6) . . . . ?
C13 C8 C9 N3 176.1(3) . . . . ?
C13 C8 C9 N10 -5.0(5) . . . . ?
C14 S1 C3 N2 -171.2(4) . . . . ?
C14 S1 C3 N4 7.4(4) . . . . ?
C15 N3 C9 N10 1.6(6) . . . . ?
C15 N3 C9 C8 -179.5(4) . . . . ?
C15 C16 C17 C18 173.6(6) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.786
