# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_sust_3609_0m
_database_code_depnum_ccdc_archive 'CCDC 2334175'
loop_
_audit_author_name
_audit_author_address
'xuyong chen'
;Shaanxi University of Science and Technology
China
;
_audit_update_record             
;
2025-03-27 deposited with the CCDC.	2025-03-28 downloaded from the CCDC.
;
_audit_creation_date             2025-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H6 O8 S2, 2(C H9 N6)'
_chemical_formula_sum            'C16 H24 N12 O8 S2'
_chemical_formula_weight         576.59
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3149(17)
_cell_length_b                   7.8964(11)
_cell_length_c                   12.7900(17)
_cell_angle_alpha                90
_cell_angle_beta                 112.156(6)
_cell_angle_gamma                90
_cell_volume                     1151.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9172
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.782
_cell_measurement_theta_min      2.909
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0597 before and 0.0561 after correction.
The Ratio of minimum to maximum transmission is 0.9426.
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    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_mounting_method   
;
 Crystals were removed from the crystallisation vial and immediately
 coated with polybutenes oil (CAS: 9003-29-6) on a glass slide.
 A suitable single crystal coated with polybutenes oil as less as possible
 was sealed in capillary tube filled with argon. The capillary tube with
 single crystal was mounted on copper pin with solid paraffin.
;
_exptl_crystal_recrystallization_method 
;
 The crystals were growth by means of evaporation of water at RT.
;
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            44427
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.847
_diffrn_reflns_theta_min         2.909
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Bruker PHOTON-II area detector'
_diffrn_detector_area_resol_mean 7.4
_diffrn_detector_type            'CMOS-PHOTONII area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON-II area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2484
_reflns_number_total             2739
_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 (Bruker, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0131(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.087
_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)+(0.0455P)²+0.5221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5A)
;
_atom_sites_solution_hydrogens   mixed
_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 0.42136(3) 0.73630(4) 0.25153(3) 0.02463(12) Uani 1 1 d . . . . .
O2 O 0.52274(10) 0.82729(14) 0.24841(9) 0.0336(3) Uani 1 1 d . . . . .
O4 O 0.31005(10) 0.81591(16) 0.18930(11) 0.0392(3) Uani 1 1 d . . . . .
O1 O 0.59550(12) 0.20624(15) -0.01376(10) 0.0401(3) Uani 1 1 d . . . . .
O3 O 0.43712(12) 0.69134(16) 0.36699(10) 0.0394(3) Uani 1 1 d . . . . .
N1 N 0.33540(12) 0.69061(17) 0.53212(11) 0.0302(3) Uani 1 1 d . . . . .
N3 N 0.31549(12) 0.96595(17) 0.58296(11) 0.0304(3) Uani 1 1 d . . . . .
N6 N 0.24991(13) 0.85632(18) 0.75097(12) 0.0307(3) Uani 1 1 d . . . . .
N5 N 0.27445(13) 0.74149(17) 0.67802(11) 0.0309(3) Uani 1 1 d . . . . .
N2 N 0.32148(14) 0.51586(18) 0.54693(13) 0.0347(3) Uani 1 1 d . . . . .
N4 N 0.36356(15) 1.0194(2) 0.50367(13) 0.0375(3) Uani 1 1 d . . . . .
C4 C 0.42403(11) 0.53703(17) 0.18604(11) 0.0216(3) Uani 1 1 d . . . . .
C3 C 0.45764(11) 0.52089(16) 0.09281(11) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.48065(11) 0.35784(16) 0.06255(11) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.30986(12) 0.79899(19) 0.59809(12) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.54005(12) 0.33529(17) -0.01846(11) 0.0233(3) Uani 1 1 d . . . . .
C7 C 0.45752(13) 0.21449(18) 0.11446(13) 0.0271(3) Uani 1 1 d . . . . .
H7 H 0.471787 0.107116 0.092606 0.033 Uiso 1 1 calc R U . . .
C6 C 0.41333(14) 0.23242(19) 0.19849(14) 0.0309(3) Uani 1 1 d . . . . .
H6 H 0.392039 0.137440 0.229332 0.037 Uiso 1 1 calc R U . . .
C5 C 0.40096(13) 0.39357(19) 0.23655(13) 0.0284(3) Uani 1 1 d . . . . .
H5A H 0.376813 0.405188 0.296864 0.034 Uiso 1 1 calc R U . . .
H6A H 0.303(2) 0.840(3) 0.823(2) 0.046(6) Uiso 1 1 d . . . . .
H2A H 0.389(2) 0.465(3) 0.5552(19) 0.049(6) Uiso 1 1 d . . . . .
H4A H 0.424(2) 1.075(3) 0.539(2) 0.053(6) Uiso 1 1 d . . . . .
H3 H 0.3241(18) 1.029(3) 0.6386(18) 0.042(5) Uiso 1 1 d . . . . .
H1 H 0.3607(19) 0.729(3) 0.4859(19) 0.045(6) Uiso 1 1 d . . . . .
H2B H 0.269(2) 0.474(3) 0.482(2) 0.054(6) Uiso 1 1 d . . . . .
H6B H 0.182(2) 0.823(3) 0.7529(18) 0.048(6) Uiso 1 1 d . . . . .
H5 H 0.2715(17) 0.636(3) 0.6863(16) 0.035(5) Uiso 1 1 d . . . . .
H4B H 0.316(2) 1.091(3) 0.456(2) 0.060(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4540(11) . ?
S1 O4 1.4439(12) . ?
S1 O3 1.4588(12) . ?
S1 C4 1.7888(14) . ?
O1 C1 1.2155(17) . ?
N1 N2 1.4120(19) . ?
N1 C8 1.3204(19) . ?
N1 H1 0.82(2) . ?
N3 N4 1.4177(19) . ?
N3 C8 1.338(2) . ?
N3 H3 0.84(2) . ?
N6 N5 1.4131(18) . ?
N6 H6A 0.91(2) . ?
N6 H6B 0.89(2) . ?
N5 C8 1.3333(19) . ?
N5 H5 0.84(2) . ?
N2 H2A 0.89(2) . ?
N2 H2B 0.90(2) . ?
N4 H4A 0.83(3) . ?
N4 H4B 0.88(3) . ?
C4 C3 1.4077(18) . ?
C4 C5 1.3856(19) . ?
C3 C2 1.4037(17) . ?
C3 C1 1.4884(18) 3_665 ?
C2 C1 1.4873(18) . ?
C2 C7 1.395(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.383(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.391(2) . ?
C5 H5A 0.9300 . ?

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
O2 S1 O3 111.12(7) . . ?
O2 S1 C4 104.72(6) . . ?
O4 S1 O2 114.60(8) . . ?
O4 S1 O3 113.59(7) . . ?
O4 S1 C4 107.82(7) . . ?
O3 S1 C4 103.95(7) . . ?
N2 N1 H1 123.7(16) . . ?
C8 N1 N2 118.52(13) . . ?
C8 N1 H1 117.7(16) . . ?
N4 N3 H3 118.4(14) . . ?
C8 N3 N4 117.07(13) . . ?
C8 N3 H3 117.1(14) . . ?
N5 N6 H6A 108.9(14) . . ?
N5 N6 H6B 105.4(14) . . ?
H6A N6 H6B 104.8(19) . . ?
N6 N5 H5 121.4(13) . . ?
C8 N5 N6 120.07(13) . . ?
C8 N5 H5 118.4(13) . . ?
N1 N2 H2A 107.6(15) . . ?
N1 N2 H2B 108.6(15) . . ?
H2A N2 H2B 105(2) . . ?
N3 N4 H4A 107.5(16) . . ?
N3 N4 H4B 109.3(16) . . ?
H4A N4 H4B 105(2) . . ?
C3 C4 S1 122.65(10) . . ?
C5 C4 S1 117.23(10) . . ?
C5 C4 C3 119.90(12) . . ?
C4 C3 C1 123.69(12) . 3_665 ?
C2 C3 C4 118.10(12) . . ?
C2 C3 C1 117.99(11) . 3_665 ?
C3 C2 C1 120.36(12) . . ?
C7 C2 C3 120.96(12) . . ?
C7 C2 C1 118.47(12) . . ?
N1 C8 N3 120.56(14) . . ?
N1 C8 N5 119.66(14) . . ?
N5 C8 N3 119.75(13) . . ?
O1 C1 C3 121.70(13) . 3_665 ?
O1 C1 C2 118.73(13) . . ?
C2 C1 C3 119.12(11) . 3_665 ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.84(13) . . ?
C6 C7 H7 120.1 . . ?
C7 C6 H6 120.2 . . ?
C7 C6 C5 119.52(13) . . ?
C5 C6 H6 120.2 . . ?
C4 C5 C6 121.06(13) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?

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
_geom_hbond_publ_flag
C5 H5A O4 0.93 2.48 3.1443(18) 128.9 2_545 yes
N4 H4A O2 0.83(3) 2.66(2) 3.1831(19) 121.8(19) 3_676 yes
N3 H3 O2 0.84(2) 2.21(2) 2.8364(17) 131.4(18) 3_676 yes
N1 H1 O3 0.82(2) 2.09(2) 2.8329(17) 150(2) . yes
N6 H6B O2 0.89(2) 2.27(2) 3.1402(19) 166(2) 4_576 yes

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 C4 C3 C2 166.80(10) . . . . ?
S1 C4 C3 C1 -18.81(18) . . . 3_665 ?
S1 C4 C5 C6 -173.12(12) . . . . ?
O2 S1 C4 C3 -37.56(13) . . . . ?
O2 S1 C4 C5 137.07(12) . . . . ?
O4 S1 C4 C3 84.89(12) . . . . ?
O4 S1 C4 C5 -100.48(12) . . . . ?
O3 S1 C4 C3 -154.25(12) . . . . ?
O3 S1 C4 C5 20.39(13) . . . . ?
N6 N5 C8 N1 178.32(14) . . . . ?
N6 N5 C8 N3 -3.9(2) . . . . ?
N2 N1 C8 N3 -176.27(14) . . . . ?
N2 N1 C8 N5 1.5(2) . . . . ?
N4 N3 C8 N1 -7.7(2) . . . . ?
N4 N3 C8 N5 174.55(14) . . . . ?
C4 C3 C2 C1 -167.07(12) . . . . ?
C4 C3 C2 C7 7.52(19) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C3 C2 C1 O1 154.07(14) . . . . ?
C3 C2 C1 C3 -18.4(2) . . . 3_665 ?
C3 C2 C7 C6 -1.2(2) . . . . ?
C2 C7 C6 C5 -5.0(2) . . . . ?
C1 C3 C2 C1 18.2(2) 3_665 . . . ?
C1 C3 C2 C7 -167.19(12) 3_665 . . . ?
C1 C2 C7 C6 173.47(13) . . . . ?
C7 C2 C1 O1 -20.7(2) . . . . ?
C7 C2 C1 C3 166.85(12) . . . 3_665 ?
C7 C6 C5 C4 4.8(2) . . . . ?
C5 C4 C3 C2 -7.7(2) . . . . ?
C5 C4 C3 C1 166.70(13) . . . 3_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy_5
_database_code_depnum_ccdc_archive 'CCDC 2334206'
loop_
_audit_author_name
_audit_author_address
'xuyong chen'
;Shaanxi University of Science and Technology
China
;
_audit_update_record             
;
2025-03-27 deposited with the CCDC.	2025-03-28 downloaded from the CCDC.
;
_audit_creation_date             2025-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H6 O8 S2, 2(C H9 N6)'
_chemical_formula_sum            'C16 H24 N12 O8 S2'
_chemical_formula_weight         576.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOS
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'
O O 0.0492 0.0322 '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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.88320(10)
_cell_length_b                   14.6525(2)
_cell_length_c                   23.2897(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2348.91(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5105
_cell_measurement_temperature    212.99(10)
_cell_measurement_theta_max      76.1620
_cell_measurement_theta_min      6.0150
_shelx_estimated_absorpt_T_max   0.687
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    2.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7211
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.458
_diffrn_reflns_theta_min         6.040
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      212.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  27.00   1.00    0.10    --   48.67 -19.00 150.00   49
  2  ω     39.00 110.00   1.00    0.10    --  106.65-122.00 161.00   71
  3  ω    -14.00  25.00   1.00    0.10    --   48.67 -17.00-127.00   39
  4  ω     60.00 103.00   1.00    0.10    --  106.65 -77.00-180.00   43
  5  ω    104.00 167.00   1.00    0.10    --  106.65 111.00 157.00   63
  6  ω     95.00 175.00   1.00    0.10    --  106.65  19.00  90.00   80
  7  ω   -160.00-101.00   1.00    0.10    --  -91.75 -17.00-127.00   59
  8  ω    -80.00 -54.00   1.00    0.10    --  -91.75 111.00 157.00   26
  9  ω    -27.00  26.00   1.00    0.10    --  -48.67  19.00 120.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0365804000
_diffrn_orient_matrix_UB_12      -0.0970665000
_diffrn_orient_matrix_UB_13      -0.0228393000
_diffrn_orient_matrix_UB_21      -0.0338122000
_diffrn_orient_matrix_UB_22      -0.0389073000
_diffrn_orient_matrix_UB_23      0.0606371000
_diffrn_orient_matrix_UB_31      -0.2183551000
_diffrn_orient_matrix_UB_32      -0.0103297000
_diffrn_orient_matrix_UB_33      -0.0132703000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2122
_reflns_number_total             2327
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0059(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²+0.8292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1127
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C6(H6), N1(H1), N5(H5), N3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.73081(6) 0.19840(3) 0.61925(2) 0.02127(18) Uani 1 1 d . . . . .
O3 O 0.5398(2) 0.17837(9) 0.64205(6) 0.0370(4) Uani 1 1 d . . . . .
O1 O 0.78445(19) 0.53816(9) 0.42508(6) 0.0307(3) Uani 1 1 d . . . . .
O4 O 0.8155(2) 0.12448(8) 0.58653(6) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.8619(2) 0.23169(9) 0.66351(6) 0.0378(4) Uani 1 1 d . . . . .
C3 C 0.5203(2) 0.42027(10) 0.53643(6) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.5342(2) 0.34350(11) 0.57198(7) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.430781 0.327554 0.596365 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6718(2) 0.44192(11) 0.49904(7) 0.0199(4) Uani 1 1 d . . . . .
C5 C 0.7020(3) 0.29124(11) 0.57082(7) 0.0202(4) Uani 1 1 d . . . . .
C1 C 0.6572(2) 0.52182(11) 0.46007(7) 0.0206(4) Uani 1 1 d . . . . .
C7 C 0.8386(3) 0.38781(12) 0.49773(7) 0.0249(4) Uani 1 1 d . . . . .
H7 H 0.940083 0.402060 0.472267 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8549(3) 0.31299(11) 0.53396(7) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.968206 0.277206 0.533651 0.030 Uiso 1 1 calc R U . . .
N1 N 0.8424(2) 0.50512(10) 0.70747(7) 0.0295(4) Uani 1 1 d . . . . .
H1 H 0.862547 0.563601 0.709981 0.035 Uiso 1 1 calc R U . . .
N5 N 0.8207(2) 0.49313(10) 0.80575(7) 0.0291(4) Uani 1 1 d . . . . .
H5 H 0.819701 0.460077 0.836781 0.035 Uiso 1 1 calc R U . . .
N6 N 0.8285(3) 0.58898(11) 0.80881(8) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.8378(3) 0.46095(11) 0.65377(7) 0.0312(4) Uani 1 1 d . . . . .
N3 N 0.7834(2) 0.36572(10) 0.74950(7) 0.0283(4) Uani 1 1 d . . . . .
H3 H 0.774637 0.339483 0.716091 0.034 Uiso 1 1 calc R U . . .
N4 N 0.7645(3) 0.31531(12) 0.80086(7) 0.0313(4) Uani 1 1 d . . . . .
C8 C 0.8150(2) 0.45459(11) 0.75424(8) 0.0222(4) Uani 1 1 d . . . . .
H4A H 0.656(4) 0.2882(17) 0.8019(10) 0.036(6) Uiso 1 1 d . . . . .
H2A H 0.961(5) 0.4650(19) 0.6366(13) 0.058(8) Uiso 1 1 d . . . . .
H4B H 0.861(4) 0.277(2) 0.8015(11) 0.047(7) Uiso 1 1 d . . . . .
H6A H 0.932(4) 0.6015(19) 0.8297(12) 0.051(7) Uiso 1 1 d . . . . .
H6B H 0.724(4) 0.6086(17) 0.8275(10) 0.031(6) Uiso 1 1 d . . . . .
H2B H 0.756(4) 0.498(2) 0.6326(12) 0.053(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4477(14) . ?
S1 O4 1.4469(13) . ?
S1 O2 1.4541(14) . ?
S1 C5 1.7782(16) . ?
O1 C1 1.220(2) . ?
C3 C4 1.400(2) . ?
C3 C2 1.395(2) . ?
C3 C1 1.489(2) 5_666 ?
C4 H4 0.9400 . ?
C4 C5 1.387(2) . ?
C2 C1 1.485(2) . ?
C2 C7 1.395(2) . ?
C5 C6 1.395(2) . ?
C7 H7 0.9400 . ?
C7 C6 1.388(2) . ?
C6 H6 0.9400 . ?
N1 H1 0.8700 . ?
N1 N2 1.409(2) . ?
N1 C8 1.330(2) . ?
N5 H5 0.8700 . ?
N5 N6 1.407(2) . ?
N5 C8 1.327(2) . ?
N6 H6A 0.88(3) . ?
N6 H6B 0.89(3) . ?
N2 H2A 0.94(3) . ?
N2 H2B 0.93(3) . ?
N3 H3 0.8700 . ?
N3 N4 1.412(2) . ?
N3 C8 1.325(2) . ?
N4 H4A 0.85(3) . ?
N4 H4B 0.87(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
O3 S1 O2 111.80(9) . . ?
O3 S1 C5 106.66(8) . . ?
O4 S1 O3 114.02(9) . . ?
O4 S1 O2 112.00(9) . . ?
O4 S1 C5 106.46(8) . . ?
O2 S1 C5 105.19(8) . . ?
C4 C3 C1 118.78(14) . 5_666 ?
C2 C3 C4 120.05(15) . . ?
C2 C3 C1 121.17(14) . 5_666 ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.29(15) . . ?
C5 C4 H4 120.4 . . ?
C3 C2 C1 120.67(14) . . ?
C3 C2 C7 119.95(15) . . ?
C7 C2 C1 119.38(15) . . ?
C4 C5 S1 120.20(13) . . ?
C4 C5 C6 120.95(15) . . ?
C6 C5 S1 118.77(13) . . ?
O1 C1 C3 120.90(15) . 5_666 ?
O1 C1 C2 120.94(15) . . ?
C2 C1 C3 118.13(14) . 5_666 ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.14(16) . . ?
C6 C7 H7 119.9 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.59(16) . . ?
C7 C6 H6 120.2 . . ?
N2 N1 H1 121.0 . . ?
C8 N1 H1 121.0 . . ?
C8 N1 N2 117.90(15) . . ?
N6 N5 H5 120.9 . . ?
C8 N5 H5 120.9 . . ?
C8 N5 N6 118.15(16) . . ?
N5 N6 H6A 105.5(18) . . ?
N5 N6 H6B 108.4(16) . . ?
H6A N6 H6B 108(2) . . ?
N1 N2 H2A 109.2(18) . . ?
N1 N2 H2B 102.4(18) . . ?
H2A N2 H2B 107(2) . . ?
N4 N3 H3 121.3 . . ?
C8 N3 H3 121.3 . . ?
C8 N3 N4 117.31(15) . . ?
N3 N4 H4A 110.5(17) . . ?
N3 N4 H4B 106.4(18) . . ?
H4A N4 H4B 112(3) . . ?
N5 C8 N1 119.95(15) . . ?
N3 C8 N1 120.14(16) . . ?
N3 C8 N5 119.91(16) . . ?

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
_geom_hbond_publ_flag
N1 H1 O3 0.87 2.40 3.070(2) 133.6 8_765 yes
N5 H5 O1 0.87 2.18 2.908(2) 141.3 2_665 yes
N3 H3 O2 0.87 2.09 2.857(2) 147.1 . yes
N4 H4A O2 0.85(3) 2.33(3) 3.142(2) 160(2) 6_557 yes
N2 H2A O1 0.94(3) 2.27(3) 3.183(2) 165(3) 5_766 yes
N4 H4B O3 0.87(3) 2.31(3) 3.063(2) 145(2) 6_657 yes
N6 H6A O2 0.88(3) 2.38(3) 3.054(2) 133(2) 3_756 yes
N6 H6B O3 0.89(3) 2.20(3) 3.075(2) 167(2) 3_656 yes
N2 H2B O4 0.93(3) 2.19(3) 3.051(2) 153(2) 8_765 yes

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 C7 -177.03(13) . . . . ?
O3 S1 C5 C4 15.98(16) . . . . ?
O3 S1 C5 C6 -167.22(14) . . . . ?
O4 S1 C5 C4 138.08(14) . . . . ?
O4 S1 C5 C6 -45.11(16) . . . . ?
O2 S1 C5 C4 -102.90(15) . . . . ?
O2 S1 C5 C6 73.90(15) . . . . ?
C3 C4 C5 S1 175.36(12) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C3 C2 C1 O1 -175.93(16) . . . . ?
C3 C2 C1 C3 2.1(2) . . . 5_666 ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C4 C3 C2 C1 178.51(14) . . . . ?
C4 C3 C2 C7 -1.0(2) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C2 C7 C6 C5 1.3(3) . . . . ?
C1 C3 C4 C5 -177.34(14) 5_666 . . . ?
C1 C3 C2 C1 -2.2(3) 5_666 . . . ?
C1 C3 C2 C7 178.31(15) 5_666 . . . ?
C1 C2 C7 C6 179.85(15) . . . . ?
C7 C2 C1 O1 3.6(2) . . . . ?
C7 C2 C1 C3 -178.37(15) . . . 5_666 ?
N6 N5 C8 N1 8.8(3) . . . . ?
N6 N5 C8 N3 -171.62(17) . . . . ?
N2 N1 C8 N5 179.11(17) . . . . ?
N2 N1 C8 N3 -0.4(3) . . . . ?
N4 N3 C8 N1 177.12(17) . . . . ?
N4 N3 C8 N5 -2.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.867
