# 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 2021

####################################################################### 
# 
# 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 2068028'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N6 O2 S'
_chemical_formula_sum            'C16 H18 N6 O2 S'
_chemical_formula_weight         358.42

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   14.3997(9)
_cell_length_b                   14.7521(9)
_cell_length_c                   7.6031(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.0910(10)
_cell_angle_gamma                90
_cell_volume                     1605.98(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    561
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21741
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         30.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4882
_reflns_number_gt                4115
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.5419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4882
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_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_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 0.45401(2) 0.42226(2) 0.85052(4) 0.01650(8) Uani 1 1 d . . . . .
O1 O 0.04899(6) 0.56737(6) 0.77365(12) 0.02107(19) Uani 1 1 d . . . . .
O2 O 0.24945(6) 0.30477(6) 0.57178(12) 0.02096(19) Uani 1 1 d . . . . .
N1 N 0.15227(7) 0.51448(6) 1.00589(13) 0.01439(18) Uani 1 1 d . . . . .
N2 N 0.11170(7) 0.42207(6) 0.77842(12) 0.01324(18) Uani 1 1 d . . . . .
N3 N 0.26387(7) 0.41612(7) 1.18468(13) 0.01626(19) Uani 1 1 d . . . . .
H3N H 0.2645(12) 0.4467(12) 1.284(2) 0.030(4) Uiso 1 1 d . . . . .
N4 N 0.34766(7) 0.43654(7) 1.11413(13) 0.01663(19) Uani 1 1 d . . . . .
N5 N 0.27663(6) 0.37991(6) 0.83732(12) 0.01234(18) Uani 1 1 d . . . . .
N6 N 0.68414(7) 0.43662(7) 0.50866(14) 0.0189(2) Uani 1 1 d . . . . .
C1 C 0.09901(7) 0.50790(7) 0.84485(15) 0.0144(2) Uani 1 1 d . . . . .
C2 C 0.17812(8) 0.42265(7) 1.06935(14) 0.0128(2) Uani 1 1 d . . . . .
H2A H 0.126158 0.397424 1.131885 0.015 Uiso 1 1 calc R U . . .
C3 C 0.18046(7) 0.37201(7) 0.89171(14) 0.01187(19) Uani 1 1 d . . . . .
H3A H 0.161726 0.307116 0.902040 0.014 Uiso 1 1 calc R U . . .
C4 C 0.34966(8) 0.41548(8) 0.95205(15) 0.0139(2) Uani 1 1 d . . . . .
C5 C 0.30165(8) 0.34625(7) 0.67974(15) 0.0133(2) Uani 1 1 d . . . . .
C6 C 0.40139(7) 0.36863(7) 0.66013(14) 0.0130(2) Uani 1 1 d . . . . .
C7 C 0.43804(8) 0.34787(7) 0.50909(15) 0.0136(2) Uani 1 1 d . . . . .
H7A H 0.396995 0.317270 0.422665 0.016 Uiso 1 1 calc R U . . .
C8 C 0.53139(8) 0.36546(7) 0.45874(14) 0.0134(2) Uani 1 1 d . . . . .
C9 C 0.59837(8) 0.42010(8) 0.55590(16) 0.0166(2) Uani 1 1 d . . . . .
H9A H 0.581998 0.447115 0.661768 0.020 Uiso 1 1 calc R U . . .
C10 C 0.70682(8) 0.39744(8) 0.35985(17) 0.0196(2) Uani 1 1 d . . . . .
H10A H 0.767775 0.407065 0.326413 0.024 Uiso 1 1 calc R U . . .
C11 C 0.64534(9) 0.34332(9) 0.25200(17) 0.0209(2) Uani 1 1 d . . . . .
H11A H 0.663778 0.317544 0.146590 0.025 Uiso 1 1 calc R U . . .
C12 C 0.55681(8) 0.32777(8) 0.30120(15) 0.0176(2) Uani 1 1 d . . . . .
H12A H 0.513493 0.291755 0.228665 0.021 Uiso 1 1 calc R U . . .
C13 C 0.13092(8) 0.58555(8) 1.12998(16) 0.0176(2) Uani 1 1 d . . . . .
H13A H 0.139593 0.561211 1.251963 0.021 Uiso 1 1 calc R U . . .
H13B H 0.064703 0.603742 1.104089 0.021 Uiso 1 1 calc R U . . .
C14 C 0.19281(9) 0.66824(9) 1.11834(18) 0.0230(3) Uani 1 1 d . . . . .
H14A H 0.176940 0.713872 1.203923 0.034 Uiso 1 1 calc R U . . .
H14B H 0.183018 0.693612 0.998680 0.034 Uiso 1 1 calc R U . . .
H14C H 0.258411 0.650589 1.144889 0.034 Uiso 1 1 calc R U . . .
C15 C 0.06740(8) 0.39508(8) 0.60399(15) 0.0172(2) Uani 1 1 d . . . . .
H15A H 0.113606 0.400343 0.516959 0.021 Uiso 1 1 calc R U . . .
H15B H 0.015501 0.437370 0.567654 0.021 Uiso 1 1 calc R U . . .
C16 C 0.02965(8) 0.29903(8) 0.60001(17) 0.0198(2) Uani 1 1 d . . . . .
H16A H 0.000891 0.284841 0.480556 0.030 Uiso 1 1 calc R U . . .
H16B H -0.017236 0.293620 0.683911 0.030 Uiso 1 1 calc R U . . .
H16C H 0.080893 0.256582 0.633007 0.030 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 C6 1.7502(11) . ?
S1 C4 1.7635(12) . ?
O1 C1 1.2242(14) . ?
O2 C5 1.2175(13) . ?
N1 C1 1.3775(14) . ?
N1 C13 1.4648(14) . ?
N1 C2 1.4726(14) . ?
N2 C1 1.3826(14) . ?
N2 C3 1.4444(13) . ?
N2 C15 1.4645(14) . ?
N3 N4 1.4041(14) . ?
N3 C2 1.4398(14) . ?
N3 H3N 0.882(18) . ?
N4 C4 1.2742(15) . ?
N5 C5 1.3796(14) . ?
N5 C4 1.3956(14) . ?
N5 C3 1.4913(14) . ?
N6 C10 1.3414(16) . ?
N6 C9 1.3446(15) . ?
C2 C3 1.5468(15) . ?
C2 H2A 1.0000 . ?
C3 H3A 1.0000 . ?
C5 C6 1.4964(15) . ?
C6 C7 1.3489(15) . ?
C7 C8 1.4595(15) . ?
C7 H7A 0.9500 . ?
C8 C12 1.4038(15) . ?
C8 C9 1.4052(15) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3926(18) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3853(17) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.5188(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.5167(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C6 S1 C4 91.27(5) . . ?
C1 N1 C13 119.19(10) . . ?
C1 N1 C2 108.90(9) . . ?
C13 N1 C2 120.70(9) . . ?
C1 N2 C3 111.05(9) . . ?
C1 N2 C15 121.20(9) . . ?
C3 N2 C15 127.32(9) . . ?
N4 N3 C2 117.98(9) . . ?
N4 N3 H3N 106.7(11) . . ?
C2 N3 H3N 114.8(11) . . ?
C4 N4 N3 115.20(10) . . ?
C5 N5 C4 115.42(9) . . ?
C5 N5 C3 123.26(9) . . ?
C4 N5 C3 121.09(9) . . ?
C10 N6 C9 117.38(10) . . ?
O1 C1 N1 126.06(11) . . ?
O1 C1 N2 126.10(11) . . ?
N1 C1 N2 107.85(9) . . ?
N3 C2 N1 115.57(9) . . ?
N3 C2 C3 113.75(9) . . ?
N1 C2 C3 100.74(8) . . ?
N3 C2 H2A 108.8 . . ?
N1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
N2 C3 N5 113.12(9) . . ?
N2 C3 C2 101.35(8) . . ?
N5 C3 C2 108.13(8) . . ?
N2 C3 H3A 111.3 . . ?
N5 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
N4 C4 N5 127.11(10) . . ?
N4 C4 S1 121.15(9) . . ?
N5 C4 S1 111.61(8) . . ?
O2 C5 N5 124.53(10) . . ?
O2 C5 C6 125.04(10) . . ?
N5 C5 C6 110.43(9) . . ?
C7 C6 C5 120.07(10) . . ?
C7 C6 S1 129.24(9) . . ?
C5 C6 S1 110.68(8) . . ?
C6 C7 C8 129.60(10) . . ?
C6 C7 H7A 115.2 . . ?
C8 C7 H7A 115.2 . . ?
C12 C8 C9 116.69(10) . . ?
C12 C8 C7 118.96(10) . . ?
C9 C8 C7 124.33(10) . . ?
N6 C9 C8 124.21(11) . . ?
N6 C9 H9A 117.9 . . ?
C8 C9 H9A 117.9 . . ?
N6 C10 C11 123.18(11) . . ?
N6 C10 H10A 118.4 . . ?
C11 C10 H10A 118.4 . . ?
C12 C11 C10 118.79(11) . . ?
C12 C11 H11A 120.6 . . ?
C10 C11 H11A 120.6 . . ?
C11 C12 C8 119.71(11) . . ?
C11 C12 H12A 120.1 . . ?
C8 C12 H12A 120.1 . . ?
N1 C13 C14 111.89(10) . . ?
N1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 113.13(10) . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C2 N3 N4 C4 -33.47(15) . . . . ?
C13 N1 C1 O1 18.54(17) . . . . ?
C2 N1 C1 O1 162.60(11) . . . . ?
C13 N1 C1 N2 -161.13(10) . . . . ?
C2 N1 C1 N2 -17.08(12) . . . . ?
C3 N2 C1 O1 176.04(11) . . . . ?
C15 N2 C1 O1 3.09(18) . . . . ?
C3 N2 C1 N1 -4.28(12) . . . . ?
C15 N2 C1 N1 -177.23(10) . . . . ?
N4 N3 C2 N1 -65.73(13) . . . . ?
N4 N3 C2 C3 50.13(13) . . . . ?
C1 N1 C2 N3 152.56(9) . . . . ?
C13 N1 C2 N3 -64.02(13) . . . . ?
C1 N1 C2 C3 29.52(11) . . . . ?
C13 N1 C2 C3 172.94(9) . . . . ?
C1 N2 C3 N5 -93.43(11) . . . . ?
C15 N2 C3 N5 78.98(13) . . . . ?
C1 N2 C3 C2 22.09(11) . . . . ?
C15 N2 C3 C2 -165.49(10) . . . . ?
C5 N5 C3 N2 -65.12(13) . . . . ?
C4 N5 C3 N2 120.62(11) . . . . ?
C5 N5 C3 C2 -176.52(9) . . . . ?
C4 N5 C3 C2 9.21(13) . . . . ?
N3 C2 C3 N2 -154.11(9) . . . . ?
N1 C2 C3 N2 -29.81(10) . . . . ?
N3 C2 C3 N5 -34.96(12) . . . . ?
N1 C2 C3 N5 89.34(9) . . . . ?
N3 N4 C4 N5 4.04(17) . . . . ?
N3 N4 C4 S1 -171.46(8) . . . . ?
C5 N5 C4 N4 -167.59(11) . . . . ?
C3 N5 C4 N4 7.10(17) . . . . ?
C5 N5 C4 S1 8.27(12) . . . . ?
C3 N5 C4 S1 -177.04(8) . . . . ?
C6 S1 C4 N4 171.62(10) . . . . ?
C6 S1 C4 N5 -4.52(9) . . . . ?
C4 N5 C5 O2 172.39(11) . . . . ?
C3 N5 C5 O2 -2.18(17) . . . . ?
C4 N5 C5 C6 -8.08(13) . . . . ?
C3 N5 C5 C6 177.36(9) . . . . ?
O2 C5 C6 C7 4.52(18) . . . . ?
N5 C5 C6 C7 -175.02(10) . . . . ?
O2 C5 C6 S1 -176.13(10) . . . . ?
N5 C5 C6 S1 4.34(11) . . . . ?
C4 S1 C6 C7 179.39(11) . . . . ?
C4 S1 C6 C5 0.11(8) . . . . ?
C5 C6 C7 C8 177.93(10) . . . . ?
S1 C6 C7 C8 -1.30(19) . . . . ?
C6 C7 C8 C12 172.61(12) . . . . ?
C6 C7 C8 C9 -8.97(19) . . . . ?
C10 N6 C9 C8 -0.62(18) . . . . ?
C12 C8 C9 N6 -1.14(17) . . . . ?
C7 C8 C9 N6 -179.59(11) . . . . ?
C9 N6 C10 C11 1.73(18) . . . . ?
N6 C10 C11 C12 -1.00(19) . . . . ?
C10 C11 C12 C8 -0.89(18) . . . . ?
C9 C8 C12 C11 1.86(17) . . . . ?
C7 C8 C12 C11 -179.61(11) . . . . ?
C1 N1 C13 C14 -96.93(13) . . . . ?
C2 N1 C13 C14 123.31(11) . . . . ?
C1 N2 C15 C16 -139.53(11) . . . . ?
C3 N2 C15 C16 48.75(15) . . . . ?

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
N3 H3N N6 0.882(18) 2.395(18) 3.2163(15) 155.1(15) 3_667

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.055

