# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_exp_788
_database_code_depnum_ccdc_archive 'CCDC 2177562'
loop_
_audit_author_name
_audit_author_address
'Pavel Slepukhin'
;Postovsky Institute of Organic Synthesis of Ural Division of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-06-07 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2015-12-09
_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         'C12.75 H14.25 N7 O4 S, 0.25(C H3)'
_chemical_formula_sum            'C13 H15 N7 O4 S'
_chemical_formula_weight         365.38
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   18.226(3)
_cell_length_b                   12.3104(11)
_cell_length_c                   7.2437(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.275(16)
_cell_angle_gamma                90.00
_cell_volume                     1608.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    825
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.6700
_cell_measurement_theta_min      2.7940
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5855
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.26
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9776
_diffrn_measured_fraction_theta_max 0.9776
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   18.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360  -99.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   87.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   57.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega    8.00   88.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   38.0000   30.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0282635000
_diffrn_orient_matrix_UB_12      0.0101190000
_diffrn_orient_matrix_UB_13      0.0557749000
_diffrn_orient_matrix_UB_21      -0.0259943000
_diffrn_orient_matrix_UB_22      0.0080101000
_diffrn_orient_matrix_UB_23      -0.0816128000
_diffrn_orient_matrix_UB_31      -0.0087636000
_diffrn_orient_matrix_UB_32      -0.0561150000
_diffrn_orient_matrix_UB_33      -0.0016590000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1893
_reflns_number_total             3198
_reflns_odcompleteness_completeness 80.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.0450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1483
_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     direct
_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
N7 N 0.13877(13) 0.18781(17) -0.0942(3) 0.0386(6) Uani 1 1 d . . .
N1 N 0.10560(13) -0.02849(16) -0.1201(3) 0.0396(6) Uani 1 1 d . . .
O3 O 0.22758(12) -0.02482(15) -0.2031(3) 0.0489(6) Uani 1 1 d . . .
N6 N 0.07372(15) 0.15308(19) -0.1868(4) 0.0417(7) Uani 1 1 d . . .
N12 N 0.37904(15) 0.2029(2) 0.2004(4) 0.0591(8) Uani 1 1 d . . .
N3 N 0.00254(14) -0.12052(18) -0.2163(4) 0.0449(7) Uani 1 1 d . . .
O1 O 0.31374(14) -0.0615(2) 0.2084(4) 0.0737(8) Uani 1 1 d . . .
C4 C -0.00986(16) -0.0107(2) -0.2544(4) 0.0387(7) Uani 1 1 d . . .
N13 N 0.35441(16) 0.3009(2) 0.1792(4) 0.0631(8) Uani 1 1 d . . .
C9 C 0.18327(17) -0.0028(2) -0.0608(5) 0.0390(7) Uani 1 1 d . . .
C5 C 0.05384(16) 0.0458(2) -0.1933(4) 0.0361(7) Uani 1 1 d . . .
O4 O -0.08783(14) 0.13206(16) -0.3664(4) 0.0712(8) Uani 1 1 d . . .
C8 C 0.18918(16) 0.1173(2) -0.0285(4) 0.0377(7) Uani 1 1 d . . .
N15 N -0.13498(17) -0.0369(2) -0.3949(5) 0.0578(9) Uani 1 1 d . . .
C11 C 0.32737(18) 0.1248(2) 0.1374(5) 0.0462(8) Uani 1 1 d . . .
C2 C 0.07128(18) -0.1276(2) -0.1373(4) 0.0462(8) Uani 1 1 d . . .
H2 H 0.0944 -0.1926 -0.0972 0.055 Uiso 1 1 calc R . .
O2 O 0.42321(15) 0.0006(2) 0.1509(5) 0.0936(10) Uani 1 1 d . . .
C21 C -0.07976(18) 0.0338(2) -0.3429(4) 0.0459(8) Uani 1 1 d . . .
C10 C 0.25888(17) 0.1658(2) 0.0610(4) 0.0398(7) Uani 1 1 d . . .
C14 C 0.3525(2) 0.0110(3) 0.1689(5) 0.0587(10) Uani 1 1 d . A .
C22 C 0.2448(2) -0.1378(3) -0.2263(6) 0.0675(11) Uani 1 1 d . . .
H22A H 0.2027 -0.1751 -0.2955 0.081 Uiso 1 1 calc R . .
H22B H 0.2571 -0.1726 -0.1057 0.081 Uiso 1 1 calc R . .
C23 C 0.3093(3) -0.1420(4) -0.3305(7) 0.1079(18) Uani 1 1 d . . .
H23A H 0.2951 -0.1136 -0.4538 0.162 Uiso 1 1 calc R . .
H23B H 0.3253 -0.2159 -0.3385 0.162 Uiso 1 1 calc R . .
H23C H 0.3491 -0.0993 -0.2665 0.162 Uiso 1 1 calc R . .
C17 C 0.4599(15) -0.105(2) 0.174(2) 0.086(3) Uani 0.50 1 d PDU A 2
H17A H 0.5075 -0.1002 0.1289 0.103 Uiso 0.50 1 calc PR A 2
H17B H 0.4301 -0.1582 0.0990 0.103 Uiso 0.50 1 calc PR A 2
S1 S 0.26579(5) 0.30291(6) 0.07692(13) 0.0535(3) Uani 1 1 d . . .
C20 C 0.4604(8) -0.1639(13) 0.077(2) 0.161(6) Uani 0.50 1 d P A 1
H20A H 0.4858 -0.1254 -0.0096 0.242 Uiso 0.50 1 calc PR A 1
H20B H 0.4104 -0.1785 0.0213 0.242 Uiso 0.50 1 calc PR A 1
H20C H 0.4855 -0.2312 0.1106 0.242 Uiso 0.50 1 calc PR A 1
C19 C 0.484(2) -0.091(2) 0.391(3) 0.108(7) Uani 0.25 1 d PDU B 3
H19A H 0.5137 -0.0267 0.4160 0.162 Uiso 0.25 1 d PR B 3
H19B H 0.4391 -0.0833 0.4447 0.162 Uiso 0.25 1 d PR B 3
H19C H 0.5112 -0.1527 0.4440 0.162 Uiso 0.25 1 d PR B 3
C18 C 0.4596(15) -0.101(2) 0.236(2) 0.086(3) Uani 0.50 1 d PU A 1
H18A H 0.5094 -0.0873 0.2990 0.103 Uiso 0.50 1 calc PR A 1
H18B H 0.4305 -0.1350 0.3225 0.103 Uiso 0.50 1 calc PR A 1
H9 H 0.1987(16) -0.044(2) 0.046(4) 0.041(8) Uiso 1 1 d . . .
C12 C 0.472(2) -0.141(2) 0.379(3) 0.108(7) Uani 0.25 1 d PDU A 2
H12A H 0.4272 -0.1735 0.4091 0.162 Uiso 0.25 1 calc PR A 2
H12B H 0.4847 -0.0795 0.4581 0.162 Uiso 0.25 1 calc PR A 2
H12C H 0.5114 -0.1935 0.3978 0.162 Uiso 0.25 1 calc PR A 2
H6 H 0.047(2) 0.202(3) -0.219(5) 0.064(12) Uiso 1 1 d . . .
H15A H -0.1281(18) -0.099(3) -0.387(4) 0.048(10) Uiso 1 1 d . . .
H15B H -0.173(2) -0.016(3) -0.478(5) 0.078(13) 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
N7 N6 1.345(3) . ?
N7 C8 1.303(3) . ?
N1 C9 1.454(4) . ?
N1 C5 1.365(3) . ?
N1 C2 1.369(3) . ?
O3 C9 1.423(4) . ?
O3 C22 1.441(3) . ?
N6 C5 1.368(3) . ?
N6 H6 0.79(3) . ?
N12 N13 1.289(3) . ?
N12 C11 1.377(4) . ?
N3 C4 1.391(3) . ?
N3 C2 1.303(4) . ?
O1 C14 1.198(4) . ?
C4 C5 1.372(4) . ?
C4 C21 1.449(4) . ?
N13 S1 1.678(3) . ?
C9 C8 1.499(4) . ?
C9 H9 0.93(3) . ?
O4 C21 1.228(3) . ?
C8 C10 1.467(4) . ?
N15 C21 1.342(4) . ?
N15 H15A 0.77(3) . ?
N15 H15B 0.88(4) . ?
C11 C10 1.385(4) . ?
C11 C14 1.481(4) . ?
C2 H2 0.9300 . ?
O2 C14 1.321(4) . ?
O2 C17 1.46(2) . ?
O2 C18 1.51(2) . ?
C10 S1 1.695(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.485(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C12 1.539(18) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C18 1.38(2) . ?
C19 H19A 0.9595 . ?
C19 H19B 0.9606 . ?
C19 H19C 0.9593 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C12 H19B 1.0839 . ?
C12 H19C 0.8108 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C8 N7 N6 119.7(2) . . ?
C5 N1 C9 123.9(2) . . ?
C5 N1 C2 106.3(2) . . ?
C2 N1 C9 129.3(2) . . ?
C9 O3 C22 115.1(2) . . ?
N7 N6 C5 122.3(2) . . ?
N7 N6 H6 111(3) . . ?
C5 N6 H6 126(3) . . ?
N13 N12 C11 113.8(3) . . ?
C2 N3 C4 105.7(2) . . ?
N3 C4 C21 124.2(2) . . ?
C5 C4 N3 108.9(2) . . ?
C5 C4 C21 126.9(2) . . ?
N12 N13 S1 111.3(2) . . ?
N1 C9 C8 107.8(2) . . ?
N1 C9 H9 107.0(18) . . ?
O3 C9 N1 112.0(2) . . ?
O3 C9 C8 105.4(2) . . ?
O3 C9 H9 111.3(18) . . ?
C8 C9 H9 113.3(16) . . ?
N1 C5 N6 118.0(3) . . ?
N1 C5 C4 106.9(2) . . ?
N6 C5 C4 135.1(3) . . ?
N7 C8 C9 124.7(3) . . ?
N7 C8 C10 114.3(2) . . ?
C10 C8 C9 120.5(2) . . ?
C21 N15 H15A 121(2) . . ?
C21 N15 H15B 118(2) . . ?
H15A N15 H15B 116(3) . . ?
N12 C11 C10 114.4(3) . . ?
N12 C11 C14 115.3(3) . . ?
C10 C11 C14 130.3(3) . . ?
N1 C2 H2 123.9 . . ?
N3 C2 N1 112.2(2) . . ?
N3 C2 H2 123.9 . . ?
C14 O2 C17 120.9(11) . . ?
C14 O2 C18 114.7(10) . . ?
C17 O2 C18 17.5(11) . . ?
O4 C21 C4 120.9(3) . . ?
O4 C21 N15 122.0(3) . . ?
N15 C21 C4 117.1(3) . . ?
C8 C10 S1 119.1(2) . . ?
C11 C10 C8 134.6(3) . . ?
C11 C10 S1 106.3(2) . . ?
O1 C14 C11 124.2(3) . . ?
O1 C14 O2 124.6(3) . . ?
O2 C14 C11 111.1(3) . . ?
O3 C22 H22A 110.3 . . ?
O3 C22 H22B 110.3 . . ?
O3 C22 C23 107.2(3) . . ?
H22A C22 H22B 108.5 . . ?
C23 C22 H22A 110.3 . . ?
C23 C22 H22B 110.3 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C17 H17A 109.3 . . ?
O2 C17 H17B 109.3 . . ?
O2 C17 C12 111.7(17) . . ?
H17A C17 H17B 107.9 . . ?
C12 C17 H17A 109.3 . . ?
C12 C17 H17B 109.3 . . ?
N13 S1 C10 94.19(14) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.4 . . ?
H19B C19 H19C 109.5 . . ?
O2 C18 H18A 111.7 . . ?
O2 C18 H18B 111.7 . . ?
C20 C18 O2 100.4(12) . . ?
C20 C18 H18A 111.7 . . ?
C20 C18 H18B 111.7 . . ?
H18A C18 H18B 109.5 . . ?
C17 C12 H19B 102.8 . . ?
C17 C12 H19C 127.1 . . ?
C17 C12 H12A 109.5 . . ?
C17 C12 H12B 109.5 . . ?
C17 C12 H12C 109.5 . . ?
H19B C12 H19C 110.9 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
