# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2112834'
loop_
_audit_author_name
_audit_author_address
'Zhichun Shangguan'
;School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2021-09-29 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N4 S'
_chemical_formula_sum            'C17 H22 N4 S'
_chemical_formula_weight         314.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.6168(2)
_cell_length_b                   8.1750(2)
_cell_length_c                   39.0525(10)
_cell_angle_alpha                87.1020(10)
_cell_angle_beta                 88.922(2)
_cell_angle_gamma                73.340(2)
_cell_volume                     1715.70(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9525
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.6567
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.680
_shelx_estimated_absorpt_T_min   0.799
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34076
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         3.399
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6270
_reflns_number_gt                4630
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0550P)²+0.3850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6270
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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 0.35281(10) 0.19063(7) 0.74434(2) 0.03846(15) Uani 1 1 d . . . . .
C1 C 1.1215(4) 0.0303(3) 0.91939(5) 0.0422(5) Uani 1 1 d . . . . .
N1 N 1.1246(3) -0.0759(2) 0.94732(4) 0.0445(4) Uani 1 1 d . . . . .
N3 N 0.9678(3) 0.0254(2) 0.89183(4) 0.0400(4) Uani 1 1 d . . . . .
C3 C 1.3713(5) 0.0687(3) 0.95821(6) 0.0551(6) Uani 1 1 d . . . . .
H3 H 1.486236 0.112000 0.969731 0.066 Uiso 1 1 calc R U . . .
S2 S -0.11666(10) 0.66826(7) 0.76135(2) 0.03867(15) Uani 1 1 d . . . . .
C2 C 1.2810(4) 0.1255(3) 0.92582(6) 0.0510(6) Uani 1 1 d . . . . .
H2 H 1.319891 0.210987 0.911242 0.061 Uiso 1 1 calc R U . . .
N2 N 1.2784(4) -0.0546(3) 0.97159(5) 0.0522(5) Uani 1 1 d . . . . .
N5 N -0.5301(4) 1.1641(3) 0.55249(5) 0.0529(5) Uani 1 1 d . . . . .
C5 C 0.8266(4) 0.1389(3) 0.83948(5) 0.0360(5) Uani 1 1 d . . . . .
N4 N 0.9804(3) 0.1343(2) 0.86814(4) 0.0415(4) Uani 1 1 d . . . . .
C4 C 0.9917(4) -0.2038(3) 0.95297(6) 0.0534(6) Uani 1 1 d . . . . .
H4A H 0.865172 -0.188236 0.935210 0.080 Uiso 1 1 calc R U . . .
H4B H 0.911428 -0.191029 0.975573 0.080 Uiso 1 1 calc R U . . .
H4C H 1.109001 -0.318231 0.951945 0.080 Uiso 1 1 calc R U . . .
N7 N -0.3889(3) 1.0765(2) 0.60922(4) 0.0435(4) Uani 1 1 d . . . . .
C7 C 0.7152(4) 0.2668(3) 0.78282(5) 0.0376(5) Uani 1 1 d . . . . .
H7 H 0.737830 0.341528 0.764417 0.045 Uiso 1 1 calc R U . . .
C6 C 0.8537(4) 0.2483(3) 0.81239(5) 0.0408(5) Uani 1 1 d . . . . .
H6 H 0.969945 0.311944 0.814174 0.049 Uiso 1 1 calc R U . . .
N6 N -0.5144(4) 1.2730(3) 0.52614(5) 0.0640(6) Uani 1 1 d . . . . .
C8 C 0.5434(4) 0.1758(2) 0.78013(5) 0.0322(4) Uani 1 1 d . . . . .
N8 N -0.2427(3) 1.0989(2) 0.63152(4) 0.0431(4) Uani 1 1 d . . . . .
C9 C 0.5145(4) 0.0656(3) 0.80767(5) 0.0378(5) Uani 1 1 d . . . . .
H9 H 0.396539 0.003126 0.806023 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2611(4) 0.3759(3) 0.68436(5) 0.0367(5) Uani 1 1 d . . . . .
H12A H 0.301816 0.265361 0.673095 0.044 Uiso 1 1 calc R U . . .
H12B H 0.083911 0.405463 0.691262 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4207(4) 0.3553(3) 0.71638(5) 0.0349(5) Uani 1 1 d . . . . .
H11A H 0.381545 0.464437 0.728125 0.042 Uiso 1 1 calc R U . . .
H11B H 0.599086 0.322027 0.710052 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6541(4) 0.0464(3) 0.83701(5) 0.0390(5) Uani 1 1 d . . . . .
H10 H 0.633200 -0.029063 0.855391 0.047 Uiso 1 1 calc R U . . .
C13 C 0.2986(4) 0.5132(3) 0.65870(5) 0.0391(5) Uani 1 1 d . . . . .
H13A H 0.258512 0.623841 0.669901 0.047 Uiso 1 1 calc R U . . .
H13B H 0.475356 0.483401 0.651566 0.047 Uiso 1 1 calc R U . . .
C14 C 0.1364(4) 0.5322(3) 0.62709(5) 0.0415(5) Uani 1 1 d . . . . .
H14A H -0.039087 0.554857 0.634510 0.050 Uiso 1 1 calc R U . . .
H14B H 0.183105 0.422756 0.615388 0.050 Uiso 1 1 calc R U . . .
C15 C 0.1575(5) 0.6746(3) 0.60156(6) 0.0507(6) Uani 1 1 d . . . . .
H15A H 0.136804 0.780821 0.613867 0.061 Uiso 1 1 calc R U . . .
H15B H 0.325431 0.643165 0.591082 0.061 Uiso 1 1 calc R U . . .
C16 C -0.0332(6) 0.7073(4) 0.57385(7) 0.0694(8) Uani 1 1 d . . . . .
H16 H -0.200714 0.729345 0.581414 0.083 Uiso 1 1 calc R U . . .
C17 C -0.0016(7) 0.7095(4) 0.54211(7) 0.0919(11) Uani 1 1 d . . . . .
H17A H 0.161383 0.688450 0.532815 0.110 Uiso 1 1 calc R U . . .
H17B H -0.140438 0.732151 0.527252 0.110 Uiso 1 1 calc R U . . .
C18 C -0.3961(4) 1.1838(3) 0.57986(5) 0.0462(5) Uani 1 1 d . . . . .
C19 C -0.2898(5) 1.3115(3) 0.57093(6) 0.0551(6) Uani 1 1 d . . . . .
H19 H -0.185404 1.355269 0.584465 0.066 Uiso 1 1 calc R U . . .
C20 C -0.3692(6) 1.3620(3) 0.53779(6) 0.0644(7) Uani 1 1 d . . . . .
H20 H -0.325425 1.450221 0.524692 0.077 Uiso 1 1 calc R U . . .
C21 C -0.6715(5) 1.0413(4) 0.54886(7) 0.0649(7) Uani 1 1 d . . . . .
H21A H -0.826962 1.097437 0.536748 0.097 Uiso 1 1 calc R U . . .
H21B H -0.709117 0.998609 0.571616 0.097 Uiso 1 1 calc R U . . .
H21C H -0.573317 0.945571 0.535769 0.097 Uiso 1 1 calc R U . . .
C22 C -0.2243(4) 0.9927(3) 0.66177(5) 0.0371(5) Uani 1 1 d . . . . .
C23 C -0.3556(4) 0.8725(3) 0.66868(5) 0.0394(5) Uani 1 1 d . . . . .
H23 H -0.470520 0.857168 0.652481 0.047 Uiso 1 1 calc R U . . .
C24 C -0.3165(4) 0.7771(3) 0.69906(5) 0.0375(5) Uani 1 1 d . . . . .
H24 H -0.405638 0.695647 0.703663 0.045 Uiso 1 1 calc R U . . .
C25 C -0.1482(4) 0.7970(2) 0.72351(5) 0.0328(4) Uani 1 1 d . . . . .
C26 C -0.0177(4) 0.9165(3) 0.71633(5) 0.0367(5) Uani 1 1 d . . . . .
H26 H 0.097817 0.931949 0.732426 0.044 Uiso 1 1 calc R U . . .
C27 C -0.0570(4) 1.0120(3) 0.68574(5) 0.0406(5) Uani 1 1 d . . . . .
H27 H 0.032803 1.092962 0.681002 0.049 Uiso 1 1 calc R U . . .
C28 C 0.1090(4) 0.7318(3) 0.78617(5) 0.0347(5) Uani 1 1 d . . . . .
H28A H 0.265121 0.716682 0.772894 0.042 Uiso 1 1 calc R U . . .
H28B H 0.043751 0.853806 0.791465 0.042 Uiso 1 1 calc R U . . .
C29 C 0.1590(4) 0.6212(3) 0.81923(5) 0.0377(5) Uani 1 1 d . . . . .
H29A H 0.225340 0.499824 0.813558 0.045 Uiso 1 1 calc R U . . .
H29B H 0.000454 0.634278 0.831808 0.045 Uiso 1 1 calc R U . . .
C30 C 0.3429(4) 0.6679(3) 0.84230(5) 0.0377(5) Uani 1 1 d . . . . .
H30A H 0.499113 0.659372 0.829401 0.045 Uiso 1 1 calc R U . . .
H30B H 0.273507 0.787930 0.848728 0.045 Uiso 1 1 calc R U . . .
C31 C 0.4009(4) 0.5529(3) 0.87470(5) 0.0415(5) Uani 1 1 d . . . . .
H31A H 0.464997 0.432698 0.868155 0.050 Uiso 1 1 calc R U . . .
H31B H 0.244922 0.564004 0.887798 0.050 Uiso 1 1 calc R U . . .
C32 C 0.5905(4) 0.5934(3) 0.89788(5) 0.0481(6) Uani 1 1 d . . . . .
H32A H 0.737956 0.598169 0.884030 0.058 Uiso 1 1 calc R U . . .
H32B H 0.516982 0.707484 0.907164 0.058 Uiso 1 1 calc R U . . .
C33 C 0.6712(5) 0.4650(3) 0.92697(6) 0.0638(7) Uani 1 1 d . . . . .
H33 H 0.739770 0.349631 0.920998 0.077 Uiso 1 1 calc R U . . .
C34 C 0.6587(5) 0.4922(4) 0.95928(7) 0.0677(8) Uani 1 1 d . . . . .
H34A H 0.591784 0.605013 0.966797 0.081 Uiso 1 1 calc R U . . .
H34B H 0.716415 0.399451 0.975561 0.081 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 C8 1.7545(19) . ?
S1 C11 1.8112(19) . ?
C1 N1 1.356(3) . ?
C1 C2 1.378(3) . ?
C1 N3 1.402(3) . ?
N1 N2 1.344(2) . ?
N1 C4 1.455(3) . ?
N3 N4 1.267(2) . ?
C3 N2 1.341(3) . ?
C3 C2 1.379(3) . ?
S2 C25 1.752(2) . ?
S2 C28 1.8142(19) . ?
N5 N6 1.345(3) . ?
N5 C18 1.361(3) . ?
N5 C21 1.461(3) . ?
C5 C6 1.385(3) . ?
C5 C10 1.397(3) . ?
C5 N4 1.419(2) . ?
N7 N8 1.264(2) . ?
N7 C18 1.402(3) . ?
C7 C6 1.382(3) . ?
C7 C8 1.385(3) . ?
N6 C20 1.337(4) . ?
C8 C9 1.405(3) . ?
N8 C22 1.418(2) . ?
C9 C10 1.377(3) . ?
C12 C13 1.524(3) . ?
C12 C11 1.526(3) . ?
C13 C14 1.523(3) . ?
C14 C15 1.524(3) . ?
C15 C16 1.497(3) . ?
C16 C17 1.249(4) . ?
C18 C19 1.371(3) . ?
C19 C20 1.381(3) . ?
C22 C27 1.384(3) . ?
C22 C23 1.401(3) . ?
C23 C24 1.372(3) . ?
C24 C25 1.403(3) . ?
C25 C26 1.395(3) . ?
C26 C27 1.379(3) . ?
C28 C29 1.521(3) . ?
C29 C30 1.523(3) . ?
C30 C31 1.520(3) . ?
C31 C32 1.527(3) . ?
C32 C33 1.491(3) . ?
C33 C34 1.289(3) . ?

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 S1 C11 104.42(9) . . ?
N1 C1 C2 107.26(19) . . ?
N1 C1 N3 118.7(2) . . ?
C2 C1 N3 134.0(2) . . ?
N2 N1 C1 111.55(19) . . ?
N2 N1 C4 119.77(19) . . ?
C1 N1 C4 128.67(18) . . ?
N4 N3 C1 111.30(18) . . ?
N2 C3 C2 112.3(2) . . ?
C25 S2 C28 104.20(9) . . ?
C1 C2 C3 104.4(2) . . ?
C3 N2 N1 104.48(18) . . ?
N6 N5 C18 111.3(2) . . ?
N6 N5 C21 120.1(2) . . ?
C18 N5 C21 128.5(2) . . ?
C6 C5 C10 119.34(18) . . ?
C6 C5 N4 114.90(18) . . ?
C10 C5 N4 125.75(19) . . ?
N3 N4 C5 114.63(18) . . ?
N8 N7 C18 111.75(19) . . ?
C6 C7 C8 119.70(19) . . ?
C7 C6 C5 121.42(19) . . ?
C20 N6 N5 104.3(2) . . ?
C7 C8 C9 118.98(18) . . ?
C7 C8 S1 124.15(15) . . ?
C9 C8 S1 116.87(14) . . ?
N7 N8 C22 114.69(18) . . ?
C10 C9 C8 121.21(19) . . ?
C13 C12 C11 112.96(16) . . ?
C12 C11 S1 107.64(13) . . ?
C9 C10 C5 119.35(19) . . ?
C14 C13 C12 112.02(17) . . ?
C13 C14 C15 113.86(18) . . ?
C16 C15 C14 112.0(2) . . ?
C17 C16 C15 128.6(3) . . ?
N5 C18 C19 107.4(2) . . ?
N5 C18 N7 118.3(2) . . ?
C19 C18 N7 134.2(2) . . ?
C18 C19 C20 104.2(2) . . ?
N6 C20 C19 112.6(2) . . ?
C27 C22 C23 119.17(19) . . ?
C27 C22 N8 114.95(18) . . ?
C23 C22 N8 125.88(19) . . ?
C24 C23 C22 119.37(19) . . ?
C23 C24 C25 121.64(19) . . ?
C26 C25 C24 118.56(18) . . ?
C26 C25 S2 124.30(15) . . ?
C24 C25 S2 117.14(15) . . ?
C27 C26 C25 119.68(19) . . ?
C26 C27 C22 121.58(19) . . ?
C29 C28 S2 108.52(14) . . ?
C28 C29 C30 112.46(17) . . ?
C31 C30 C29 112.54(17) . . ?
C30 C31 C32 113.76(18) . . ?
C33 C32 C31 113.0(2) . . ?
C34 C33 C32 127.6(3) . . ?

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 C1 N1 N2 -0.1(3) . . . . ?
N3 C1 N1 N2 -179.31(18) . . . . ?
C2 C1 N1 C4 -178.8(2) . . . . ?
N3 C1 N1 C4 2.0(3) . . . . ?
N1 C1 N3 N4 178.38(18) . . . . ?
C2 C1 N3 N4 -0.6(4) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
N3 C1 C2 C3 178.9(2) . . . . ?
N2 C3 C2 C1 0.4(3) . . . . ?
C2 C3 N2 N1 -0.4(3) . . . . ?
C1 N1 N2 C3 0.3(3) . . . . ?
C4 N1 N2 C3 179.1(2) . . . . ?
C1 N3 N4 C5 -179.10(17) . . . . ?
C6 C5 N4 N3 -175.27(18) . . . . ?
C10 C5 N4 N3 5.7(3) . . . . ?
C8 C7 C6 C5 0.7(3) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?
N4 C5 C6 C7 -179.65(19) . . . . ?
C18 N5 N6 C20 -0.4(3) . . . . ?
C21 N5 N6 C20 -178.5(2) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C6 C7 C8 S1 178.88(16) . . . . ?
C11 S1 C8 C7 -4.1(2) . . . . ?
C11 S1 C8 C9 175.03(16) . . . . ?
C18 N7 N8 C22 -179.29(17) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
S1 C8 C9 C10 -179.44(16) . . . . ?
C13 C12 C11 S1 179.34(14) . . . . ?
C8 S1 C11 C12 179.94(14) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
N4 C5 C10 C9 179.04(19) . . . . ?
C11 C12 C13 C14 -179.65(18) . . . . ?
C12 C13 C14 C15 176.92(18) . . . . ?
C13 C14 C15 C16 -170.9(2) . . . . ?
C14 C15 C16 C17 -126.1(3) . . . . ?
N6 N5 C18 C19 0.2(3) . . . . ?
C21 N5 C18 C19 178.1(2) . . . . ?
N6 N5 C18 N7 -178.57(19) . . . . ?
C21 N5 C18 N7 -0.7(4) . . . . ?
N8 N7 C18 N5 174.7(2) . . . . ?
N8 N7 C18 C19 -3.7(4) . . . . ?
N5 C18 C19 C20 0.0(3) . . . . ?
N7 C18 C19 C20 178.6(3) . . . . ?
N5 N6 C20 C19 0.5(3) . . . . ?
C18 C19 C20 N6 -0.3(3) . . . . ?
N7 N8 C22 C27 177.57(19) . . . . ?
N7 N8 C22 C23 -1.5(3) . . . . ?
C27 C22 C23 C24 0.3(3) . . . . ?
N8 C22 C23 C24 179.31(19) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C23 C24 C25 S2 179.66(16) . . . . ?
C28 S2 C25 C26 0.8(2) . . . . ?
C28 S2 C25 C24 -179.25(16) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
S2 C25 C26 C27 -179.76(16) . . . . ?
C25 C26 C27 C22 0.1(3) . . . . ?
C23 C22 C27 C26 -0.4(3) . . . . ?
N8 C22 C27 C26 -179.52(19) . . . . ?
C25 S2 C28 C29 -177.54(14) . . . . ?
S2 C28 C29 C30 -178.72(14) . . . . ?
C28 C29 C30 C31 -177.73(18) . . . . ?
C29 C30 C31 C32 178.37(18) . . . . ?
C30 C31 C32 C33 -172.1(2) . . . . ?
C31 C32 C33 C34 -123.3(3) . . . . ?

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_t_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2112835'
loop_
_audit_author_name
_audit_author_address
'Zhichun Shangguan'
;School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2021-09-29 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N4 S'
_chemical_formula_sum            'C11 H12 N4 S'
_chemical_formula_weight         232.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.1876(19)
_cell_length_b                   9.2946(14)
_cell_length_c                   12.4426(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.262(19)
_cell_angle_gamma                90
_cell_volume                     1141.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6289
_cell_measurement_theta_min      4.47
_cell_measurement_theta_max      68.21

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   0.6494
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.333
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13012
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.478
_diffrn_reflns_theta_max         68.297
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2087
_reflns_number_gt                1789
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0559P)²+0.2083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2087
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.77064(4) 1.07140(4) 0.43296(3) 0.04631(16) Uani 1 1 d . . . . .
C1 C 0.64616(15) 0.93860(16) 0.42657(13) 0.0380(3) Uani 1 1 d . . . . .
N1 N 0.33368(13) 0.63204(14) 0.37709(11) 0.0437(3) Uani 1 1 d . . . . .
N2 N 0.30902(14) 0.57114(13) 0.46075(12) 0.0425(3) Uani 1 1 d . . . . .
C2 C 0.62702(16) 0.86124(17) 0.51784(13) 0.0413(4) Uani 1 1 d . . . . .
H2 H 0.683136 0.878456 0.587800 0.050 Uiso 1 1 calc R U . . .
N3 N 0.16031(14) 0.40361(15) 0.51154(12) 0.0473(3) Uani 1 1 d . . . . .
C3 C 0.52578(16) 0.75969(17) 0.50514(13) 0.0415(4) Uani 1 1 d . . . . .
H3 H 0.513846 0.709018 0.566487 0.050 Uiso 1 1 calc R U . . .
N4 N 0.05963(15) 0.31059(16) 0.46959(15) 0.0582(4) Uani 1 1 d . . . . .
C4 C 0.44128(15) 0.73266(16) 0.40078(13) 0.0385(3) Uani 1 1 d . . . . .
C5 C 0.46104(17) 0.80869(18) 0.30954(13) 0.0443(4) Uani 1 1 d . . . . .
H5 H 0.405706 0.790346 0.239471 0.053 Uiso 1 1 calc R U . . .
C6 C 0.56154(17) 0.91059(17) 0.32206(14) 0.0442(4) Uani 1 1 d . . . . .
H6 H 0.573216 0.961124 0.260578 0.053 Uiso 1 1 calc R U . . .
C8 C 0.20307(16) 0.47255(17) 0.43020(14) 0.0430(4) Uani 1 1 d . . . . .
C7 C 0.86147(18) 1.07439(19) 0.57564(15) 0.0508(4) Uani 1 1 d . . . . .
H7A H 0.899293 0.980997 0.596855 0.076 Uiso 1 1 calc R U . . .
H7B H 0.800838 1.099694 0.620683 0.076 Uiso 1 1 calc R U . . .
H7C H 0.933036 1.144095 0.585954 0.076 Uiso 1 1 calc R U . . .
C9 C 0.12654(18) 0.42088(18) 0.32980(16) 0.0516(4) Uani 1 1 d . . . . .
H9 H 0.131876 0.446553 0.258758 0.062 Uiso 1 1 calc R U . . .
C10 C 0.04018(19) 0.3220(2) 0.35989(18) 0.0604(5) Uani 1 1 d . . . . .
H10 H -0.024274 0.269321 0.309158 0.072 Uiso 1 1 calc R U . . .
C11 C 0.2122(2) 0.4167(2) 0.63027(17) 0.0629(5) Uani 1 1 d . . . . .
H11A H 0.308468 0.402142 0.649235 0.094 Uiso 1 1 calc R U . . .
H11B H 0.170274 0.345739 0.666892 0.094 Uiso 1 1 calc R U . . .
H11C H 0.192356 0.511047 0.653498 0.094 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 C1 1.7574(16) . ?
S1 C7 1.7887(18) . ?
C1 C6 1.396(2) . ?
C1 C2 1.398(2) . ?
N1 N2 1.2632(18) . ?
N1 C4 1.416(2) . ?
N2 C8 1.395(2) . ?
C2 C3 1.378(2) . ?
N3 N4 1.345(2) . ?
N3 C8 1.357(2) . ?
N3 C11 1.446(2) . ?
C3 C4 1.393(2) . ?
N4 C10 1.334(3) . ?
C4 C5 1.393(2) . ?
C5 C6 1.375(2) . ?
C8 C9 1.385(2) . ?
C9 C10 1.386(3) . ?

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
C1 S1 C7 104.30(8) . . ?
C6 C1 C2 118.88(14) . . ?
C6 C1 S1 116.50(12) . . ?
C2 C1 S1 124.62(12) . . ?
N2 N1 C4 115.17(13) . . ?
N1 N2 C8 111.55(14) . . ?
C3 C2 C1 120.62(14) . . ?
N4 N3 C8 111.62(15) . . ?
N4 N3 C11 120.17(15) . . ?
C8 N3 C11 128.18(15) . . ?
C2 C3 C4 120.24(14) . . ?
C10 N4 N3 104.65(14) . . ?
C3 C4 C5 119.21(14) . . ?
C3 C4 N1 125.62(14) . . ?
C5 C4 N1 115.17(14) . . ?
C6 C5 C4 120.67(15) . . ?
C5 C6 C1 120.37(15) . . ?
N3 C8 C9 107.22(15) . . ?
N3 C8 N2 118.41(15) . . ?
C9 C8 N2 134.34(16) . . ?
C8 C9 C10 103.88(17) . . ?
N4 C10 C9 112.63(17) . . ?

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
C7 S1 C1 C6 -178.26(13) . . . . ?
C7 S1 C1 C2 1.87(16) . . . . ?
C4 N1 N2 C8 -179.24(12) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
S1 C1 C2 C3 179.43(12) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C8 N3 N4 C10 0.24(19) . . . . ?
C11 N3 N4 C10 -177.91(16) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 N1 -179.67(15) . . . . ?
N2 N1 C4 C3 5.3(2) . . . . ?
N2 N1 C4 C5 -174.78(14) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
N1 C4 C5 C6 179.32(14) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
S1 C1 C6 C5 -179.77(13) . . . . ?
N4 N3 C8 C9 -0.39(19) . . . . ?
C11 N3 C8 C9 177.59(17) . . . . ?
N4 N3 C8 N2 -178.95(13) . . . . ?
C11 N3 C8 N2 -1.0(2) . . . . ?
N1 N2 C8 N3 -176.78(13) . . . . ?
N1 N2 C8 C9 5.1(3) . . . . ?
N3 C8 C9 C10 0.35(19) . . . . ?
N2 C8 C9 C10 178.59(17) . . . . ?
N3 N4 C10 C9 0.0(2) . . . . ?
C8 C9 C10 N4 -0.2(2) . . . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.035



