# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_10d
_database_code_depnum_ccdc_archive 'CCDC 2095496'
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             
;
2021-07-09 deposited with the CCDC.	2021-08-16 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         'C14 H17 N5 O2 S'
_chemical_formula_sum            'C14 H17 N5 O2 S'
_chemical_formula_weight         319.38

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'

_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                   16.2034(5)
_cell_length_b                   9.9224(3)
_cell_length_c                   10.1872(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.899(2)
_cell_angle_gamma                90
_cell_volume                     1596.53(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    273
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST, Photon III detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22399
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.424
_diffrn_reflns_theta_max         29.997
_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             4640
_reflns_number_gt                3533
_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 APEX3'
_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)+(0.0480P)²+0.3988P] 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         4640
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.74115(2) 0.51491(4) 0.38667(4) 0.05041(12) Uani 1 1 d . . . . .
O1 O 0.51915(8) 0.69828(12) 0.08548(13) 0.0629(3) Uani 1 1 d . . . . .
O2 O 0.99473(9) 0.63995(14) 1.22644(13) 0.0732(4) Uani 1 1 d . . . . .
N1 N 0.64609(8) 0.58505(13) 0.13440(13) 0.0473(3) Uani 1 1 d . . . . .
N2 N 0.53827(7) 0.49960(13) 0.20595(14) 0.0466(3) Uani 1 1 d . . . . .
N3 N 0.61984(8) 0.34029(13) 0.36490(13) 0.0452(3) Uani 1 1 d . . . . .
H3N H 0.5822(12) 0.2941(19) 0.3901(18) 0.058(5) Uiso 1 1 d . . . . .
N4 N 0.68870(8) 0.37535(13) 0.58449(13) 0.0486(3) Uani 1 1 d . . . . .
N5 N 0.75354(8) 0.44962(14) 0.66818(13) 0.0487(3) Uani 1 1 d . . . . .
C1 C 0.56285(10) 0.60359(15) 0.13821(15) 0.0455(3) Uani 1 1 d . . . . .
C2 C 0.60251(9) 0.39435(14) 0.23203(14) 0.0404(3) Uani 1 1 d . . . . .
H2A H 0.588496 0.322177 0.165089 0.048 Uiso 1 1 calc R U . . .
C3 C 0.67922(9) 0.40387(14) 0.45948(15) 0.0411(3) Uani 1 1 d . . . . .
C4 C 0.68092(9) 0.47174(14) 0.21383(15) 0.0424(3) Uani 1 1 d . . . . .
H4A H 0.715283 0.416633 0.166578 0.051 Uiso 1 1 calc R U . . .
C5 C 0.76806(9) 0.40667(16) 0.78859(15) 0.0480(3) Uani 1 1 d . . . . .
H5A H 0.738429 0.331061 0.806371 0.058 Uiso 1 1 calc R U . . .
C6 C 0.82809(9) 0.46797(15) 0.90089(15) 0.0447(3) Uani 1 1 d . . . . .
C7 C 0.84788(10) 0.39990(16) 1.02218(16) 0.0497(3) Uani 1 1 d . . . . .
H7A H 0.823123 0.316422 1.029155 0.060 Uiso 1 1 calc R U . . .
C8 C 0.90360(10) 0.45250(18) 1.13379(16) 0.0530(4) Uani 1 1 d . . . . .
H8A H 0.916687 0.404327 1.214075 0.064 Uiso 1 1 calc R U . . .
C9 C 0.93933(10) 0.57712(18) 1.12420(17) 0.0530(4) Uani 1 1 d . . . . .
C10 C 0.91944(11) 0.64719(18) 1.00354(19) 0.0585(4) Uani 1 1 d . . . . .
H10A H 0.943160 0.731665 0.997435 0.070 Uiso 1 1 calc R U . . .
C11 C 0.86536(10) 0.59367(17) 0.89332(17) 0.0529(4) Uani 1 1 d . . . . .
H11A H 0.853345 0.641420 0.812745 0.063 Uiso 1 1 calc R U . . .
C12 C 0.69688(13) 0.6918(2) 0.0966(2) 0.0696(5) Uani 1 1 d . . . . .
H12A H 0.661004 0.753045 0.036690 0.104 Uiso 1 1 calc R U . . .
H12B H 0.737903 0.653882 0.052279 0.104 Uiso 1 1 calc R U . . .
H12C H 0.725473 0.739382 0.175827 0.104 Uiso 1 1 calc R U . . .
C13 C 0.45126(10) 0.4756(2) 0.2136(2) 0.0668(5) Uani 1 1 d . . . . .
H13A H 0.415988 0.546411 0.167460 0.100 Uiso 1 1 calc R U . . .
H13B H 0.447411 0.473622 0.306214 0.100 Uiso 1 1 calc R U . . .
H13C H 0.432718 0.390685 0.172015 0.100 Uiso 1 1 calc R U . . .
C14 C 1.02243(15) 0.5670(3) 1.3472(2) 0.0820(6) Uani 1 1 d . . . . .
H14A H 1.061639 0.620816 1.410439 0.123 Uiso 1 1 calc R U . . .
H14B H 1.049833 0.485541 1.328880 0.123 Uiso 1 1 calc R U . . .
H14C H 0.974652 0.544889 1.384363 0.123 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 C3 1.7615(15) . ?
S1 C4 1.8624(15) . ?
O1 C1 1.2259(18) . ?
O2 C9 1.3645(19) . ?
O2 C14 1.412(3) . ?
N1 C1 1.3703(19) . ?
N1 C4 1.4260(18) . ?
N1 C12 1.445(2) . ?
N2 C1 1.3499(19) . ?
N2 C13 1.449(2) . ?
N2 C2 1.4564(18) . ?
N3 C3 1.3559(18) . ?
N3 C2 1.4244(19) . ?
N3 H3N 0.848(19) . ?
N4 C3 1.2800(19) . ?
N4 N5 1.4049(17) . ?
N5 C5 1.270(2) . ?
C2 C4 1.5309(19) . ?
C2 H2A 0.9800 . ?
C4 H4A 0.9800 . ?
C5 C6 1.459(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.382(2) . ?
C6 C11 1.395(2) . ?
C7 C8 1.386(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.378(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.386(2) . ?
C10 C11 1.368(2) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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 C4 91.53(7) . . ?
C9 O2 C14 117.24(16) . . ?
C1 N1 C4 110.93(12) . . ?
C1 N1 C12 122.12(14) . . ?
C4 N1 C12 123.51(13) . . ?
C1 N2 C13 123.70(13) . . ?
C1 N2 C2 111.16(11) . . ?
C13 N2 C2 122.44(13) . . ?
C3 N3 C2 117.26(12) . . ?
C3 N3 H3N 118.8(12) . . ?
C2 N3 H3N 119.3(13) . . ?
C3 N4 N5 113.27(12) . . ?
C5 N5 N4 111.24(13) . . ?
O1 C1 N2 127.03(14) . . ?
O1 C1 N1 124.51(14) . . ?
N2 C1 N1 108.44(12) . . ?
N3 C2 N2 115.13(12) . . ?
N3 C2 C4 108.13(11) . . ?
N2 C2 C4 101.36(11) . . ?
N3 C2 H2A 110.6 . . ?
N2 C2 H2A 110.6 . . ?
C4 C2 H2A 110.6 . . ?
N4 C3 N3 120.84(13) . . ?
N4 C3 S1 127.17(11) . . ?
N3 C3 S1 111.86(11) . . ?
N1 C4 C2 103.30(11) . . ?
N1 C4 S1 114.37(10) . . ?
C2 C4 S1 105.95(9) . . ?
N1 C4 H4A 110.9 . . ?
C2 C4 H4A 110.9 . . ?
S1 C4 H4A 110.9 . . ?
N5 C5 C6 124.39(14) . . ?
N5 C5 H5A 117.8 . . ?
C6 C5 H5A 117.8 . . ?
C7 C6 C11 117.99(14) . . ?
C7 C6 C5 118.59(14) . . ?
C11 C6 C5 123.40(14) . . ?
C6 C7 C8 121.88(15) . . ?
C6 C7 H7A 119.1 . . ?
C8 C7 H7A 119.1 . . ?
C9 C8 C7 119.12(15) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
O2 C9 C8 124.82(16) . . ?
O2 C9 C10 115.52(16) . . ?
C8 C9 C10 119.65(15) . . ?
C11 C10 C9 120.84(16) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C6 120.50(15) . . ?
C10 C11 H11A 119.8 . . ?
C6 C11 H11A 119.8 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C3 N4 N5 C5 -171.73(13) . . . . ?
C13 N2 C1 O1 7.6(3) . . . . ?
C2 N2 C1 O1 169.28(15) . . . . ?
C13 N2 C1 N1 -170.97(16) . . . . ?
C2 N2 C1 N1 -9.24(17) . . . . ?
C4 N1 C1 O1 175.43(15) . . . . ?
C12 N1 C1 O1 15.7(3) . . . . ?
C4 N1 C1 N2 -6.00(17) . . . . ?
C12 N1 C1 N2 -165.73(16) . . . . ?
C3 N3 C2 N2 -87.60(16) . . . . ?
C3 N3 C2 C4 24.88(17) . . . . ?
C1 N2 C2 N3 135.51(13) . . . . ?
C13 N2 C2 N3 -62.5(2) . . . . ?
C1 N2 C2 C4 19.10(15) . . . . ?
C13 N2 C2 C4 -178.90(15) . . . . ?
N5 N4 C3 N3 179.36(12) . . . . ?
N5 N4 C3 S1 3.8(2) . . . . ?
C2 N3 C3 N4 168.66(13) . . . . ?
C2 N3 C3 S1 -15.16(16) . . . . ?
C4 S1 C3 N4 176.17(14) . . . . ?
C4 S1 C3 N3 0.28(11) . . . . ?
C1 N1 C4 C2 17.47(16) . . . . ?
C12 N1 C4 C2 176.87(15) . . . . ?
C1 N1 C4 S1 -97.17(13) . . . . ?
C12 N1 C4 S1 62.22(18) . . . . ?
N3 C2 C4 N1 -142.49(12) . . . . ?
N2 C2 C4 N1 -21.06(14) . . . . ?
N3 C2 C4 S1 -21.92(13) . . . . ?
N2 C2 C4 S1 99.51(10) . . . . ?
C3 S1 C4 N1 125.63(11) . . . . ?
C3 S1 C4 C2 12.54(10) . . . . ?
N4 N5 C5 C6 -176.10(13) . . . . ?
N5 C5 C6 C7 -169.99(15) . . . . ?
N5 C5 C6 C11 11.5(3) . . . . ?
C11 C6 C7 C8 -0.7(2) . . . . ?
C5 C6 C7 C8 -179.23(14) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C14 O2 C9 C8 5.3(3) . . . . ?
C14 O2 C9 C10 -174.52(17) . . . . ?
C7 C8 C9 O2 179.84(16) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
O2 C9 C10 C11 179.22(16) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C6 1.0(3) . . . . ?
C7 C6 C11 C10 -0.3(2) . . . . ?
C5 C6 C11 C10 178.18(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 O1 0.848(19) 1.960(19) 2.7966(17) 168.7(18) 2_645

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_10a
_database_code_depnum_ccdc_archive 'CCDC 2095497'
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             
;
2021-08-09 deposited with the CCDC.	2021-08-16 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         'C13 H15 N5 O S'
_chemical_formula_sum            'C13 H15 N5 O S'
_chemical_formula_weight         289.36

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   9.7481(5)
_cell_length_b                   9.6628(4)
_cell_length_c                   30.3545(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2859.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    229
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6241
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41443
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2955
_reflns_number_gt                2120
_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       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_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)+(0.0447P)²+2.3493P] 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         2955
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.51179(6) 0.70511(6) 0.37183(2) 0.02442(16) Uani 1 1 d . . . . .
O1 O 0.70048(16) 0.92656(17) 0.49071(5) 0.0281(4) Uani 1 1 d . . . . .
N1 N 0.58344(18) 0.9298(2) 0.42465(6) 0.0233(4) Uani 1 1 d . . . . .
N2 N 0.50006(18) 0.8024(2) 0.47921(6) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.33500(19) 0.6723(2) 0.43525(7) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.287(3) 0.627(3) 0.4549(9) 0.040(8) Uiso 1 1 d . . . . .
N4 N 0.36954(18) 0.4720(2) 0.39573(6) 0.0246(4) Uani 1 1 d . . . . .
N5 N 0.44875(19) 0.4157(2) 0.36139(6) 0.0250(5) Uani 1 1 d . . . . .
C1 C 0.6039(2) 0.8880(2) 0.46739(8) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.3906(2) 0.8051(2) 0.44616(7) 0.0216(5) Uani 1 1 d . . . . .
H2A H 0.316145 0.870428 0.455157 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3990(2) 0.6004(2) 0.40292(7) 0.0218(5) Uani 1 1 d . . . . .
C4 C 0.4674(2) 0.8604(2) 0.40559(7) 0.0221(5) Uani 1 1 d . . . . .
H4A H 0.408934 0.926337 0.388506 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4125(2) 0.2917(2) 0.35210(7) 0.0249(5) Uani 1 1 d . . . . .
H5A H 0.334527 0.253675 0.366463 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4866(2) 0.2064(2) 0.32021(7) 0.0234(5) Uani 1 1 d . . . . .
C7 C 0.4340(2) 0.0766(3) 0.30939(8) 0.0271(5) Uani 1 1 d . . . . .
H7A H 0.348770 0.047868 0.321524 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5043(3) -0.0111(3) 0.28114(8) 0.0313(6) Uani 1 1 d . . . . .
H8A H 0.467169 -0.099044 0.273852 0.038 Uiso 1 1 calc R U . . .
C9 C 0.6289(3) 0.0303(3) 0.26360(8) 0.0353(6) Uani 1 1 d . . . . .
H9A H 0.677641 -0.029489 0.244286 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6825(3) 0.1587(3) 0.27424(8) 0.0335(6) Uani 1 1 d . . . . .
H10A H 0.768147 0.186479 0.262188 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6125(2) 0.2471(3) 0.30230(8) 0.0276(5) Uani 1 1 d . . . . .
H11A H 0.649867 0.335142 0.309339 0.033 Uiso 1 1 calc R U . . .
C12 C 0.6949(2) 0.9860(3) 0.39826(8) 0.0332(6) Uani 1 1 d . . . . .
H12A H 0.760799 1.032830 0.417526 0.050 Uiso 1 1 calc R U . . .
H12B H 0.657865 1.052339 0.376927 0.050 Uiso 1 1 calc R U . . .
H12C H 0.740958 0.910591 0.382529 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4764(3) 0.7553(3) 0.52395(8) 0.0310(6) Uani 1 1 d . . . . .
H13A H 0.556612 0.777188 0.542142 0.046 Uiso 1 1 calc R U . . .
H13B H 0.461324 0.655052 0.523934 0.046 Uiso 1 1 calc R U . . .
H13C H 0.395415 0.801924 0.536001 0.046 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 C3 1.768(2) . ?
S1 C4 1.868(2) . ?
O1 C1 1.236(3) . ?
N1 C1 1.373(3) . ?
N1 C4 1.437(3) . ?
N1 C12 1.455(3) . ?
N2 C1 1.356(3) . ?
N2 C13 1.451(3) . ?
N2 C2 1.464(3) . ?
N3 C3 1.355(3) . ?
N3 C2 1.432(3) . ?
N3 H3 0.88(3) . ?
N4 C3 1.291(3) . ?
N4 N5 1.407(3) . ?
N5 C5 1.281(3) . ?
C2 C4 1.536(3) . ?
C2 H2A 1.0000 . ?
C4 H4A 1.0000 . ?
C5 C6 1.462(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.395(3) . ?
C6 C11 1.398(3) . ?
C7 C8 1.387(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.386(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.384(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C3 S1 C4 91.30(10) . . ?
C1 N1 C4 110.93(18) . . ?
C1 N1 C12 121.45(19) . . ?
C4 N1 C12 122.70(19) . . ?
C1 N2 C13 123.89(19) . . ?
C1 N2 C2 110.58(18) . . ?
C13 N2 C2 122.10(18) . . ?
C3 N3 C2 116.96(19) . . ?
C3 N3 H3 118.8(19) . . ?
C2 N3 H3 119.5(18) . . ?
C3 N4 N5 112.02(19) . . ?
C5 N5 N4 111.94(19) . . ?
O1 C1 N2 127.0(2) . . ?
O1 C1 N1 124.3(2) . . ?
N2 C1 N1 108.73(19) . . ?
N3 C2 N2 114.71(19) . . ?
N3 C2 C4 108.07(18) . . ?
N2 C2 C4 101.58(16) . . ?
N3 C2 H2A 110.7 . . ?
N2 C2 H2A 110.7 . . ?
C4 C2 H2A 110.7 . . ?
N4 C3 N3 120.9(2) . . ?
N4 C3 S1 126.70(18) . . ?
N3 C3 S1 112.27(17) . . ?
N1 C4 C2 102.87(18) . . ?
N1 C4 S1 114.42(15) . . ?
C2 C4 S1 105.88(15) . . ?
N1 C4 H4A 111.1 . . ?
C2 C4 H4A 111.1 . . ?
S1 C4 H4A 111.1 . . ?
N5 C5 C6 122.4(2) . . ?
N5 C5 H5A 118.8 . . ?
C6 C5 H5A 118.8 . . ?
C7 C6 C11 119.0(2) . . ?
C7 C6 C5 118.7(2) . . ?
C11 C6 C5 122.2(2) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C6 119.9(2) . . ?
C10 C11 H11A 120.1 . . ?
C6 C11 H11A 120.1 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C3 N4 N5 C5 -175.2(2) . . . . ?
C13 N2 C1 O1 8.3(4) . . . . ?
C2 N2 C1 O1 167.6(2) . . . . ?
C13 N2 C1 N1 -170.1(2) . . . . ?
C2 N2 C1 N1 -10.8(3) . . . . ?
C4 N1 C1 O1 176.4(2) . . . . ?
C12 N1 C1 O1 20.7(4) . . . . ?
C4 N1 C1 N2 -5.1(3) . . . . ?
C12 N1 C1 N2 -160.9(2) . . . . ?
C3 N3 C2 N2 -87.3(2) . . . . ?
C3 N3 C2 C4 25.2(3) . . . . ?
C1 N2 C2 N3 137.0(2) . . . . ?
C13 N2 C2 N3 -63.2(3) . . . . ?
C1 N2 C2 C4 20.7(2) . . . . ?
C13 N2 C2 C4 -179.5(2) . . . . ?
N5 N4 C3 N3 -178.96(19) . . . . ?
N5 N4 C3 S1 5.6(3) . . . . ?
C2 N3 C3 N4 169.1(2) . . . . ?
C2 N3 C3 S1 -14.9(2) . . . . ?
C4 S1 C3 N4 175.5(2) . . . . ?
C4 S1 C3 N3 -0.28(17) . . . . ?
C1 N1 C4 C2 17.5(2) . . . . ?
C12 N1 C4 C2 173.0(2) . . . . ?
C1 N1 C4 S1 -96.79(19) . . . . ?
C12 N1 C4 S1 58.6(3) . . . . ?
N3 C2 C4 N1 -143.05(18) . . . . ?
N2 C2 C4 N1 -22.0(2) . . . . ?
N3 C2 C4 S1 -22.7(2) . . . . ?
N2 C2 C4 S1 98.39(16) . . . . ?
C3 S1 C4 N1 125.83(17) . . . . ?
C3 S1 C4 C2 13.28(15) . . . . ?
N4 N5 C5 C6 -174.63(19) . . . . ?
N5 C5 C6 C7 -174.9(2) . . . . ?
N5 C5 C6 C11 9.0(3) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 -176.5(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C6 0.2(4) . . . . ?
C7 C6 C11 C10 0.0(3) . . . . ?
C5 C6 C11 C10 176.1(2) . . . . ?

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 H3 O1 0.88(3) 1.92(3) 2.772(3) 162(3) 2_466

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.056

