# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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 
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data_mo_lz_llp_1019_200k_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2250116'
loop_
_audit_author_name
_audit_author_address
'liping luo'
;sichuan university
China
;
_audit_update_record             
;
2023-03-19 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;
_audit_creation_date             2022-10-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N5 O3 S'
_chemical_formula_sum            'C19 H19 N5 O3 S'
_chemical_formula_weight         397.45
_chemical_absolute_configuration ad
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.061(3)
_cell_length_b                   5.7868(13)
_cell_length_c                   16.069(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.379(9)
_cell_angle_gamma                90
_cell_volume                     970.3(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2666
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.267
_cell_measurement_theta_min      2.688
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1138 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.8637.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9135
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         1.952
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                3349
_reflns_number_total             4227
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.1318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1121
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.74781(10) 0.48922(17) 0.42012(7) 0.0351(3) Uani 1 1 d . . . . .
O1 O 0.7037(4) 0.3111(5) 0.4658(2) 0.0620(11) Uani 1 1 d . . . . .
O2 O 0.7731(3) 0.5843(4) 0.2018(2) 0.0376(7) Uani 1 1 d . . . . .
O3 O 0.8677(3) 0.4553(7) 0.4064(2) 0.0655(12) Uani 1 1 d . . . . .
N1 N 0.6537(5) 1.0443(8) 0.6554(4) 0.0765(16) Uani 1 1 d . . . . .
N2 N 0.8087(3) 0.1951(5) 0.2120(2) 0.0271(7) Uani 1 1 d . . . . .
H2 H 0.7791 0.0650 0.2261 0.032 Uiso 1 1 calc R U . . .
N3 N 0.6265(3) 0.1213(5) 0.2833(2) 0.0263(7) Uani 1 1 d . . . . .
N4 N 0.4476(4) 0.0371(6) 0.3278(3) 0.0571(12) Uani 1 1 d . . . . .
C1 C 0.7453(5) 1.0102(8) 0.6403(3) 0.0432(11) Uani 1 1 d . . . . .
C2 C 0.8611(4) 0.9586(7) 0.6214(3) 0.0358(10) Uani 1 1 d . . . . .
H2A H 0.9334 0.9463 0.6775 0.043 Uiso 1 1 calc R U . . .
H2B H 0.8799 1.0874 0.5870 0.043 Uiso 1 1 calc R U . . .
C3 C 0.8506(4) 0.7334(7) 0.5694(3) 0.0344(10) Uani 1 1 d . . . . .
H3A H 0.9353 0.6952 0.5646 0.041 Uiso 1 1 calc R U . . .
H3B H 0.8259 0.6063 0.6018 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7528(4) 0.7515(7) 0.4778(3) 0.0322(9) Uani 1 1 d . . . . .
H4A H 0.7760 0.8801 0.4454 0.039 Uiso 1 1 calc R U . . .
H4B H 0.6672 0.7844 0.4821 0.039 Uiso 1 1 calc R U . . .
C5 C 0.6276(3) 0.5427(6) 0.3159(2) 0.0251(8) Uani 1 1 d . . . . .
H5A H 0.5427 0.5470 0.3239 0.030 Uiso 1 1 calc R U . . .
H5B H 0.6430 0.6961 0.2940 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6256(3) 0.3590(6) 0.2467(3) 0.0236(8) Uani 1 1 d . . . . .
C7 C 0.7462(3) 0.3903(7) 0.2191(3) 0.0264(8) Uani 1 1 d . . . . .
C8 C 0.9174(3) 0.1787(6) 0.1842(3) 0.0258(8) Uani 1 1 d . . . . .
C9 C 0.9960(3) -0.0120(8) 0.2110(3) 0.0345(9) Uani 1 1 d . . . . .
H9 H 0.9764 -0.1262 0.2471 0.041 Uiso 1 1 calc R U . . .
C10 C 1.1033(4) -0.0372(8) 0.1853(3) 0.0447(11) Uani 1 1 d . . . . .
H10 H 1.1570 -0.1686 0.2039 0.054 Uiso 1 1 calc R U . . .
C11 C 1.1321(4) 0.1264(8) 0.1335(4) 0.0488(13) Uani 1 1 d . . . . .
H11 H 1.2064 0.1105 0.1169 0.059 Uiso 1 1 calc R U . . .
N12 N 0.5304(3) 0.0870(5) 0.3054(2) 0.0333(8) Uani 1 1 d . . . . .
C13 C 0.5108(3) 0.3838(6) 0.1618(2) 0.0241(8) Uani 1 1 d . . . . .
C14 C 0.4285(4) 0.5703(6) 0.1430(3) 0.0312(9) Uani 1 1 d . . . . .
H14 H 0.4415 0.6920 0.1848 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3272(4) 0.5832(8) 0.0641(3) 0.0386(10) Uani 1 1 d . . . . .
H15 H 0.2711 0.7124 0.0525 0.046 Uiso 1 1 calc R U . . .
C16 C 0.3077(4) 0.4091(7) 0.0028(3) 0.0372(10) Uani 1 1 d . . . . .
H16 H 0.2383 0.4182 -0.0512 0.045 Uiso 1 1 calc R U . . .
C17 C 0.3894(4) 0.2206(7) 0.0198(3) 0.0349(10) Uani 1 1 d . . . . .
H17 H 0.3765 0.1002 -0.0225 0.042 Uiso 1 1 calc R U . . .
C18 C 0.4898(4) 0.2088(7) 0.0986(3) 0.0294(9) Uani 1 1 d . . . . .
H18 H 0.5457 0.0792 0.1101 0.035 Uiso 1 1 calc R U . . .
C19 C 0.9444(4) 0.3444(8) 0.1300(3) 0.0351(9) Uani 1 1 d . . . . .
H19 H 0.8899 0.4744 0.1103 0.042 Uiso 1 1 calc R U . . .
C20 C 1.0521(4) 0.3159(8) 0.1053(3) 0.0437(11) Uani 1 1 d . . . . .
H20 H 1.0715 0.4280 0.0684 0.052 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 O1 1.441(3) . ?
S1 O3 1.428(3) . ?
S1 C4 1.769(4) . ?
S1 C5 1.786(4) . ?
O2 C7 1.217(4) . ?
N1 C1 1.134(5) . ?
N2 H2 0.8800 . ?
N2 C7 1.348(5) . ?
N2 C8 1.418(5) . ?
N3 C6 1.495(5) . ?
N3 N12 1.243(4) . ?
N4 N12 1.127(5) . ?
C1 C2 1.443(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.532(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.514(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.534(5) . ?
C6 C7 1.550(5) . ?
C6 C13 1.531(5) . ?
C8 C9 1.383(5) . ?
C8 C19 1.393(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.366(7) . ?
C11 H11 0.9500 . ?
C11 C20 1.388(7) . ?
C13 C14 1.379(5) . ?
C13 C18 1.398(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.385(5) . ?
C20 H20 0.9500 . ?

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
O1 S1 C4 107.7(2) . . ?
O1 S1 C5 109.19(19) . . ?
O3 S1 O1 118.0(2) . . ?
O3 S1 C4 109.3(2) . . ?
O3 S1 C5 108.63(19) . . ?
C4 S1 C5 103.08(18) . . ?
C7 N2 H2 116.8 . . ?
C7 N2 C8 126.4(3) . . ?
C8 N2 H2 116.8 . . ?
N12 N3 C6 111.5(3) . . ?
N1 C1 C2 178.1(5) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.3(4) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 111.8(3) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
S1 C4 H4A 109.7 . . ?
S1 C4 H4B 109.7 . . ?
C3 C4 S1 109.8(3) . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
S1 C5 H5A 109.0 . . ?
S1 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 S1 112.8(2) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
N3 C6 C5 110.8(3) . . ?
N3 C6 C7 109.1(3) . . ?
N3 C6 C13 109.4(3) . . ?
C5 C6 C7 108.7(3) . . ?
C13 C6 C5 112.9(3) . . ?
C13 C6 C7 105.8(3) . . ?
O2 C7 N2 125.7(4) . . ?
O2 C7 C6 118.1(3) . . ?
N2 C7 C6 116.1(3) . . ?
C9 C8 N2 117.8(3) . . ?
C9 C8 C19 120.1(4) . . ?
C19 C8 N2 122.1(3) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C20 119.6(4) . . ?
C20 C11 H11 120.2 . . ?
N4 N12 N3 173.9(4) . . ?
C14 C13 C6 124.0(3) . . ?
C14 C13 C18 118.0(3) . . ?
C18 C13 C6 117.9(3) . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.3(3) . . ?
C17 C18 H18 119.4 . . ?
C8 C19 H19 120.6 . . ?
C20 C19 C8 118.8(4) . . ?
C20 C19 H19 120.6 . . ?
C11 C20 H20 119.5 . . ?
C19 C20 C11 121.1(4) . . ?
C19 C20 H20 119.5 . . ?

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
S1 C5 C6 N3 48.5(3) . . . . ?
S1 C5 C6 C7 -71.4(3) . . . . ?
S1 C5 C6 C13 171.6(2) . . . . ?
O1 S1 C4 C3 64.0(4) . . . . ?
O1 S1 C5 C6 -78.2(3) . . . . ?
O3 S1 C4 C3 -65.3(4) . . . . ?
O3 S1 C5 C6 51.8(3) . . . . ?
N2 C8 C9 C10 179.7(4) . . . . ?
N2 C8 C19 C20 -179.7(4) . . . . ?
N3 C6 C7 O2 -167.8(4) . . . . ?
N3 C6 C7 N2 15.5(5) . . . . ?
N3 C6 C13 C14 133.5(4) . . . . ?
N3 C6 C13 C18 -48.0(4) . . . . ?
C1 C2 C3 C4 66.1(5) . . . . ?
C2 C3 C4 S1 178.6(3) . . . . ?
C4 S1 C5 C6 167.6(3) . . . . ?
C5 S1 C4 C3 179.3(3) . . . . ?
C5 C6 C7 O2 -46.9(5) . . . . ?
C5 C6 C7 N2 136.4(3) . . . . ?
C5 C6 C13 C14 9.6(5) . . . . ?
C5 C6 C13 C18 -171.9(3) . . . . ?
C6 C13 C14 C15 179.1(3) . . . . ?
C6 C13 C18 C17 -179.0(4) . . . . ?
C7 N2 C8 C9 156.5(4) . . . . ?
C7 N2 C8 C19 -25.0(6) . . . . ?
C7 C6 C13 C14 -109.2(4) . . . . ?
C7 C6 C13 C18 69.4(4) . . . . ?
C8 N2 C7 O2 0.6(7) . . . . ?
C8 N2 C7 C6 177.0(3) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C8 C19 C20 C11 0.1(7) . . . . ?
C9 C8 C19 C20 -1.2(6) . . . . ?
C9 C10 C11 C20 -1.2(8) . . . . ?
C10 C11 C20 C19 1.1(8) . . . . ?
N12 N3 C6 C5 61.2(4) . . . . ?
N12 N3 C6 C7 -179.2(3) . . . . ?
N12 N3 C6 C13 -63.9(4) . . . . ?
C13 C6 C7 O2 74.7(4) . . . . ?
C13 C6 C7 N2 -102.1(4) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
C14 C13 C18 C17 -0.4(5) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 0.2(6) . . . . ?
C16 C17 C18 C13 0.0(6) . . . . ?
C18 C13 C14 C15 0.6(5) . . . . ?
C19 C8 C9 C10 1.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
