# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_exp_3230_auto
_database_code_depnum_ccdc_archive 'CCDC 2487912'
loop_
_audit_author_name
_audit_author_address
'Masafumi Ueda'
;Kitasato University
Japan
;
_audit_update_record             
;
2025-09-13 deposited with the CCDC.	2025-12-10 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H8 O2 S2'
_chemical_formula_sum            'C15 H8 O2 S2'
_chemical_formula_weight         284.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H8O2S2
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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.5461(3)
_cell_length_b                   3.86020(10)
_cell_length_c                   46.3601(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.505(2)
_cell_angle_gamma                90
_cell_volume                     2413.02(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4799
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      75.0400
_cell_measurement_theta_min      3.3180
_shelx_estimated_absorpt_T_max   0.506
_shelx_estimated_absorpt_T_min   0.442
_exptl_absorpt_coefficient_mu    3.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            7033
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.867
_diffrn_reflns_theta_min         3.832
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     88.00 162.00   0.50    0.05    --  104.61  61.00 150.00  148
  2  ω    111.00 137.00   0.50    0.05    --  104.61   0.00 -30.00   52
  3  ω    152.00 177.00   0.50    0.05    --  104.61   0.00 -30.00   50
  4  ω     98.00 176.00   0.50    0.05    --  104.61  54.00-132.00  156
  5  ω     76.00 101.00   0.50    0.05    --   47.32  54.00-132.00   50
  6  ω     32.00  75.00   0.50    0.05    --  104.61 -61.00-180.00   86
  7  ω     39.00  64.00   0.50    0.05    --  104.61 -61.00 -90.00   50
  8  ω     36.00  66.00   0.50    0.05    --  104.61 -61.00 -60.00   60
  9  ω     -5.00  20.00   0.50    0.05    --   47.32 -54.00  83.00   50
 10  ω     39.00  70.00   0.50    0.05    --  104.61 -61.00 120.00   62
 11  ω     32.00  64.00   0.50    0.05    --  104.61 -54.00  83.00   64
 12  ω     86.00 111.00   0.50    0.05    --  104.61-125.00 -60.00   50
 13  ω     36.00  80.00   0.50    0.05    --  104.61-125.00 -60.00   88
 14  ω    -58.00  25.00   0.50    0.05    --  -47.32  54.00-132.00  166
 15  ω    -14.00  28.00   0.50    0.05    --  -47.32  19.00   0.00   84
 16  ω    -69.00 -27.00   0.50    0.05    --  -91.75  61.00  60.00   84
 17  ω    -48.00 -23.00   0.50    0.05    --  -91.75  45.00  60.00   50
 18  ω    -48.00 -23.00   0.50    0.05    --  -91.75  45.00   0.00   50
 19  ω    -55.00 -28.00   0.50    0.05    --  -91.75  54.00-132.00   54
 20  ω   -144.00-119.00   0.50    0.05    --  -91.75 -54.00  83.00   50
 21  ω   -163.00-119.00   0.50    0.05    --  -91.75 -61.00 150.00   88
 22  ω   -103.00 -76.00   0.50    0.05    --  -91.75 -61.00 150.00   54
 23  ω   -119.00 -37.00   0.50    0.05    --  -47.32 -54.00  83.00  164
;
_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      -0.0575592000
_diffrn_orient_matrix_UB_12      -0.2355937000
_diffrn_orient_matrix_UB_13      0.0193369000
_diffrn_orient_matrix_UB_21      -0.0982126000
_diffrn_orient_matrix_UB_22      0.1081129000
_diffrn_orient_matrix_UB_23      -0.0171591000
_diffrn_orient_matrix_UB_31      0.0097265000
_diffrn_orient_matrix_UB_32      -0.3034692000
_diffrn_orient_matrix_UB_33      -0.0211226000
_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_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2288
_reflns_number_total             2394
_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 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.043
_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)+(0.0457P)²+3.1322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C14(H14), C11(H11), C13(H13), C12(H12), C3(H3), C2(H2)
;
_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
S2 S 0.09911(3) 0.83996(11) 0.36307(2) 0.01965(13) Uani 1 1 d . . . . .
S1 S 0.31022(3) 0.93705(11) 0.33760(2) 0.01953(13) Uani 1 1 d . . . . .
O1 O 0.47219(9) 0.4537(4) 0.43191(3) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.55838(10) 0.2462(5) 0.47075(3) 0.0376(4) Uani 1 1 d . . . . .
C6 C 0.20995(12) 0.7037(4) 0.38307(4) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.21002(12) 0.7343(4) 0.31699(4) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.30215(12) 0.7524(4) 0.37215(3) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.29321(12) 0.4737(5) 0.42759(4) 0.0198(4) Uani 1 1 d . . . . .
C8 C 0.38917(12) 0.6645(5) 0.38879(4) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.451637 0.695413 0.381416 0.023 Uiso 1 1 calc R U . . .
C5 C 0.20602(12) 0.5600(5) 0.41034(4) 0.0200(4) Uani 1 1 d . . . . .
H5 H 0.143502 0.519559 0.417423 0.024 Uiso 1 1 calc R U . . .
C9 C 0.38354(12) 0.5317(5) 0.41617(4) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.22209(13) 0.6192(5) 0.28896(4) 0.0223(4) Uani 1 1 d . . . . .
H14 H 0.285002 0.637798 0.281632 0.027 Uiso 1 1 calc R U . . .
C11 C 0.03918(13) 0.5455(5) 0.31076(4) 0.0211(4) Uani 1 1 d . . . . .
H11 H -0.022941 0.514441 0.318331 0.025 Uiso 1 1 calc R U . . .
C10 C 0.11820(12) 0.6942(4) 0.32790(3) 0.0188(3) Uani 1 1 d . . . . .
C13 C 0.14276(14) 0.4781(5) 0.27183(4) 0.0247(4) Uani 1 1 d . . . . .
H13 H 0.150983 0.405339 0.252630 0.030 Uiso 1 1 calc R U . . .
C12 C 0.05124(14) 0.4429(5) 0.28267(4) 0.0249(4) Uani 1 1 d . . . . .
H12 H -0.003232 0.348336 0.270803 0.030 Uiso 1 1 calc R U . . .
C3 C 0.29550(13) 0.3218(5) 0.45602(4) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.235174 0.277220 0.464241 0.030 Uiso 1 1 calc R U . . .
C1 C 0.47647(13) 0.3073(5) 0.45926(4) 0.0266(4) Uani 1 1 d . . . . .
C2 C 0.38266(14) 0.2427(5) 0.47102(4) 0.0274(4) Uani 1 1 d . . . . .
H2 H 0.382759 0.142312 0.489733 0.033 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
S2 C6 1.7672(17) . ?
S2 C10 1.7671(17) . ?
S1 C15 1.7662(18) . ?
S1 C7 1.7662(16) . ?
O1 C9 1.377(2) . ?
O1 C1 1.384(2) . ?
O2 C1 1.207(2) . ?
C6 C7 1.405(2) . ?
C6 C5 1.386(2) . ?
C15 C14 1.397(2) . ?
C15 C10 1.396(2) . ?
C7 C8 1.387(2) . ?
C4 C5 1.401(2) . ?
C4 C9 1.397(2) . ?
C4 C3 1.440(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(2) . ?
C5 H5 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.394(2) . ?
C11 C12 1.386(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.347(3) . ?
C1 C2 1.452(3) . ?
C2 H2 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
C10 S2 C6 101.37(8) . . ?
C15 S1 C7 101.57(8) . . ?
C9 O1 C1 122.16(14) . . ?
C7 C6 S2 120.74(13) . . ?
C5 C6 S2 119.51(13) . . ?
C5 C6 C7 119.71(15) . . ?
C14 C15 S1 119.43(13) . . ?
C10 C15 S1 121.22(13) . . ?
C10 C15 C14 119.33(16) . . ?
C6 C7 S1 121.03(13) . . ?
C8 C7 S1 118.67(12) . . ?
C8 C7 C6 120.28(15) . . ?
C5 C4 C3 124.18(15) . . ?
C9 C4 C5 117.82(15) . . ?
C9 C4 C3 117.98(16) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.95(15) . . ?
C9 C8 H8 120.5 . . ?
C6 C5 C4 120.75(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
O1 C9 C4 121.01(15) . . ?
O1 C9 C8 116.55(15) . . ?
C8 C9 C4 122.45(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.30(16) . . ?
C13 C14 H14 119.8 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.01(16) . . ?
C15 C10 S2 120.90(13) . . ?
C11 C10 S2 119.01(13) . . ?
C11 C10 C15 120.07(15) . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.09(16) . . ?
C12 C13 H13 120.0 . . ?
C11 C12 C13 120.14(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.38(16) . . ?
C2 C3 H3 119.8 . . ?
O1 C1 C2 116.93(15) . . ?
O2 C1 O1 116.10(16) . . ?
O2 C1 C2 126.97(17) . . ?
C3 C2 C1 121.52(17) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?

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
S2 C6 C7 S1 -2.2(2) . . . . ?
S2 C6 C7 C8 175.93(13) . . . . ?
S2 C6 C5 C4 -175.17(14) . . . . ?
S1 C15 C14 C13 -176.18(13) . . . . ?
S1 C15 C10 S2 -0.9(2) . . . . ?
S1 C15 C10 C11 177.47(13) . . . . ?
S1 C7 C8 C9 177.73(13) . . . . ?
O1 C1 C2 C3 0.0(3) . . . . ?
O2 C1 C2 C3 -179.9(2) . . . . ?
C6 S2 C10 C15 -42.54(16) . . . . ?
C6 S2 C10 C11 139.11(14) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C15 S1 C7 C6 -41.23(16) . . . . ?
C15 S1 C7 C8 140.58(14) . . . . ?
C15 C14 C13 C12 -1.5(3) . . . . ?
C7 S1 C15 C14 -138.52(14) . . . . ?
C7 S1 C15 C10 43.03(16) . . . . ?
C7 C6 C5 C4 2.2(3) . . . . ?
C7 C8 C9 O1 -179.07(15) . . . . ?
C7 C8 C9 C4 1.7(3) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C5 C6 C7 S1 -179.62(13) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C5 C4 C9 O1 179.87(16) . . . . ?
C5 C4 C9 C8 -0.9(3) . . . . ?
C5 C4 C3 C2 179.17(19) . . . . ?
C9 O1 C1 O2 179.00(18) . . . . ?
C9 O1 C1 C2 -0.8(3) . . . . ?
C9 C4 C5 C6 -1.1(3) . . . . ?
C9 C4 C3 C2 0.7(3) . . . . ?
C14 C15 C10 S2 -179.32(13) . . . . ?
C14 C15 C10 C11 -1.0(2) . . . . ?
C14 C13 C12 C11 -0.7(3) . . . . ?
C10 S2 C6 C7 44.15(16) . . . . ?
C10 S2 C6 C5 -138.46(15) . . . . ?
C10 C15 C14 C13 2.3(3) . . . . ?
C10 C11 C12 C13 2.0(3) . . . . ?
C12 C11 C10 S2 177.22(14) . . . . ?
C12 C11 C10 C15 -1.1(3) . . . . ?
C3 C4 C5 C6 -179.61(17) . . . . ?
C3 C4 C9 O1 -1.5(3) . . . . ?
C3 C4 C9 C8 177.71(17) . . . . ?
C1 O1 C9 C4 1.7(3) . . . . ?
C1 O1 C9 C8 -177.62(16) . . . . ?

_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 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.864

####################################################################### 
# 
# 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_exp_3245_auto
_database_code_depnum_ccdc_archive 'CCDC 2487913'
loop_
_audit_author_name
_audit_author_address
'Masafumi Ueda'
;Kitasato University
Japan
;
_audit_update_record             
;
2025-09-13 deposited with the CCDC.	2025-12-10 downloaded from the CCDC.
;
_audit_creation_date             2024-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H8 O2 S2'
_chemical_formula_sum            'C15 H8 O2 S2'
_chemical_formula_weight         284.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H8O2S2
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'
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      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                   6.8001(2)
_cell_length_b                   14.5918(5)
_cell_length_c                   12.0415(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.287(3)
_cell_angle_gamma                90
_cell_volume                     1191.48(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4721
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      75.0670
_cell_measurement_theta_min      3.6840
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.251
_exptl_absorpt_coefficient_mu    3.996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7662
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.723
_diffrn_reflns_theta_min         4.769
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  73.00   0.50    0.37    --   47.20-139.00-105.00   50
  2  ω     85.00 122.00   0.50    1.49    --  104.61-139.00-105.00   74
  3  ω     34.00  85.00   0.50    1.49    --  104.61 -94.00 -60.00  102
  4  ω     34.00  99.00   0.50    1.49    --  104.61 -94.00 -90.00  130
  5  ω     66.00 113.00   0.50    1.49    --  104.61-131.00  69.00   94
  6  ω     66.00 101.00   0.50    1.49    --  104.61 -94.00 120.00   70
  7  ω     54.00  81.00   0.50    0.37    --   47.20-131.00  69.00   54
  8  ω     33.00  67.00   0.50    1.49    --  104.61 -61.00  30.00   68
  9  ω    109.00 134.00   0.50    1.49    --  104.61 131.00 140.00   50
 10  ω     89.00 134.00   0.50    1.49    --  104.61 139.00 -44.00   90
 11  ω    -31.00  24.00   0.50    0.37    --  -47.20  37.00 -90.00  110
 12  ω    -17.00  12.00   0.50    0.37    --  -47.20  19.00  60.00   58
 13  ω   -119.00 -76.00   0.50    0.37    --  -47.20   0.00 -90.00   86
 14  ω    -45.00 -20.00   0.50    1.49    --  -91.75  61.00   0.00   50
 15  ω    -46.00 -21.00   0.50    1.49    --  -91.75  45.00 -30.00   50
 16  ω    -45.00 -20.00   0.50    1.49    --  -91.75  45.00   0.00   50
 17  ω    -48.00 -23.00   0.50    1.49    --  -91.75  45.00  90.00   50
 18  ω    -73.00 -48.00   0.50    0.37    --  -47.20 131.00 140.00   50
 19  ω    -85.00 -22.00   0.50    1.49    --  -91.75 125.00-180.00  126
 20  ω   -161.00 -84.00   0.50    1.49    --  -91.75 -61.00  90.00  154
 21  ω   -161.00-118.00   0.50    1.49    --  -91.75 -77.00 150.00   86
 22  ω   -105.00 -70.00   0.50    1.49    --  -91.75 -77.00 150.00   70
 23  ω   -105.00 -76.00   0.50    0.37    --  -47.20-131.00  69.00   58
 24  ω   -122.00 -80.00   0.50    1.49    --  -91.75-139.00-105.00   84
 25  ω   -119.00 -65.00   0.50    0.37    --  -47.20-139.00-105.00  108
;
_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      0.0731005000
_diffrn_orient_matrix_UB_12      -0.0274875000
_diffrn_orient_matrix_UB_13      -0.1133698000
_diffrn_orient_matrix_UB_21      0.0250450000
_diffrn_orient_matrix_UB_22      0.1019367000
_diffrn_orient_matrix_UB_23      -0.0292574000
_diffrn_orient_matrix_UB_31      0.2135717000
_diffrn_orient_matrix_UB_32      -0.0024220000
_diffrn_orient_matrix_UB_33      0.0524607000
_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_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2078
_reflns_number_total             2288
_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 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.097
_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)+(0.0731P)²+0.8898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1306
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C5(H5), C11(H11), C14(H14), C12(H12), C13(H13)
;
_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 0.79829(8) 0.72800(4) 0.70655(4) 0.0250(2) Uani 1 1 d . . . . .
S2 S 0.36022(8) 0.73337(4) 0.78156(5) 0.0290(2) Uani 1 1 d . . . . .
O1 O 0.1331(2) 0.57817(12) 0.41893(13) 0.0260(4) Uani 1 1 d . . . . .
O2 O 0.0016(2) 0.51649(13) 0.26313(14) 0.0320(4) Uani 1 1 d . . . . .
C9 C 0.2940(3) 0.61081(16) 0.48359(18) 0.0231(5) Uani 1 1 d . . . . .
C7 C 0.4097(3) 0.68188(16) 0.65367(18) 0.0237(5) Uani 1 1 d . . . . .
C4 C 0.4842(3) 0.60685(15) 0.44773(18) 0.0218(5) Uani 1 1 d . . . . .
C10 C 0.7450(3) 0.68247(16) 0.83766(18) 0.0241(5) Uani 1 1 d . . . . .
C6 C 0.6035(3) 0.67959(15) 0.61981(18) 0.0231(5) Uani 1 1 d . . . . .
C2 C 0.3505(3) 0.53464(16) 0.27775(19) 0.0264(5) Uani 1 1 d . . . . .
H2 H 0.368939 0.507847 0.207391 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5090(3) 0.56534(16) 0.34063(19) 0.0248(5) Uani 1 1 d . . . . .
H3 H 0.636926 0.559722 0.314642 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2553(3) 0.64550(16) 0.58663(19) 0.0252(5) Uani 1 1 d . . . . .
H8 H 0.125505 0.644331 0.610767 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6397(3) 0.64084(16) 0.51885(18) 0.0231(5) Uani 1 1 d . . . . .
H5 H 0.771086 0.637189 0.497386 0.028 Uiso 1 1 calc R U . . .
C1 C 0.1519(3) 0.54125(16) 0.31423(19) 0.0267(5) Uani 1 1 d . . . . .
C15 C 0.5518(3) 0.68451(17) 0.87031(19) 0.0266(5) Uani 1 1 d . . . . .
C11 C 0.8957(3) 0.64426(17) 0.9076(2) 0.0278(5) Uani 1 1 d . . . . .
H11 H 1.025938 0.640947 0.884398 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5110(4) 0.64834(19) 0.9728(2) 0.0325(6) Uani 1 1 d . . . . .
H14 H 0.379416 0.647786 0.994364 0.039 Uiso 1 1 calc R U . . .
C12 C 0.8546(4) 0.61112(19) 1.0112(2) 0.0329(5) Uani 1 1 d . . . . .
H12 H 0.957903 0.587064 1.060176 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6627(4) 0.6130(2) 1.0436(2) 0.0355(6) Uani 1 1 d . . . . .
H13 H 0.635273 0.589963 1.114560 0.043 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 C10 1.775(2) . ?
S1 C6 1.771(2) . ?
S2 C7 1.768(2) . ?
S2 C15 1.772(2) . ?
O1 C9 1.379(3) . ?
O1 C1 1.386(3) . ?
O2 C1 1.208(3) . ?
C9 C4 1.395(3) . ?
C9 C8 1.383(3) . ?
C7 C6 1.409(3) . ?
C7 C8 1.381(3) . ?
C4 C3 1.446(3) . ?
C4 C5 1.401(3) . ?
C10 C15 1.400(3) . ?
C10 C11 1.393(3) . ?
C6 C5 1.379(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.347(3) . ?
C2 C1 1.454(3) . ?
C3 H3 0.9500 . ?
C8 H8 0.9500 . ?
C5 H5 0.9500 . ?
C15 C14 1.389(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(4) . ?
C13 H13 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
C6 S1 C10 100.48(10) . . ?
C7 S2 C15 100.10(10) . . ?
C9 O1 C1 121.65(17) . . ?
O1 C9 C4 121.7(2) . . ?
O1 C9 C8 115.91(19) . . ?
C8 C9 C4 122.4(2) . . ?
C6 C7 S2 120.33(17) . . ?
C8 C7 S2 119.12(17) . . ?
C8 C7 C6 120.5(2) . . ?
C9 C4 C3 117.8(2) . . ?
C9 C4 C5 118.1(2) . . ?
C5 C4 C3 124.1(2) . . ?
C15 C10 S1 120.01(17) . . ?
C11 C10 S1 119.86(17) . . ?
C11 C10 C15 120.1(2) . . ?
C7 C6 S1 119.63(17) . . ?
C5 C6 S1 120.56(17) . . ?
C5 C6 C7 119.8(2) . . ?
C3 C2 H2 119.0 . . ?
C3 C2 C1 122.0(2) . . ?
C1 C2 H2 119.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.0 . . ?
C9 C8 H8 120.7 . . ?
C7 C8 C9 118.5(2) . . ?
C7 C8 H8 120.7 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
O1 C1 C2 116.85(19) . . ?
O2 C1 O1 116.6(2) . . ?
O2 C1 C2 126.6(2) . . ?
C10 C15 S2 120.16(18) . . ?
C14 C15 S2 120.14(18) . . ?
C14 C15 C10 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?

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 C10 C15 S2 -0.5(3) . . . . ?
S1 C10 C15 C14 179.67(18) . . . . ?
S1 C10 C11 C12 178.19(18) . . . . ?
S1 C6 C5 C4 -176.68(17) . . . . ?
S2 C7 C6 S1 0.4(3) . . . . ?
S2 C7 C6 C5 -178.73(17) . . . . ?
S2 C7 C8 C9 175.84(17) . . . . ?
S2 C15 C14 C13 -177.8(2) . . . . ?
O1 C9 C4 C3 -1.3(3) . . . . ?
O1 C9 C4 C5 -179.50(19) . . . . ?
O1 C9 C8 C7 -178.0(2) . . . . ?
C9 O1 C1 O2 -178.4(2) . . . . ?
C9 O1 C1 C2 2.7(3) . . . . ?
C9 C4 C3 C2 2.0(3) . . . . ?
C9 C4 C5 C6 -2.0(3) . . . . ?
C7 S2 C15 C10 46.6(2) . . . . ?
C7 S2 C15 C14 -133.7(2) . . . . ?
C7 C6 C5 C4 2.4(3) . . . . ?
C4 C9 C8 C7 3.5(3) . . . . ?
C10 S1 C6 C7 45.8(2) . . . . ?
C10 S1 C6 C5 -135.09(19) . . . . ?
C10 C15 C14 C13 2.0(4) . . . . ?
C10 C11 C12 C13 2.3(4) . . . . ?
C6 S1 C10 C15 -45.9(2) . . . . ?
C6 S1 C10 C11 133.78(19) . . . . ?
C6 C7 C8 C9 -3.0(3) . . . . ?
C3 C4 C5 C6 179.9(2) . . . . ?
C3 C2 C1 O1 -2.0(3) . . . . ?
C3 C2 C1 O2 179.2(2) . . . . ?
C8 C9 C4 C3 177.2(2) . . . . ?
C8 C9 C4 C5 -1.0(3) . . . . ?
C8 C7 C6 S1 179.21(17) . . . . ?
C8 C7 C6 C5 0.1(3) . . . . ?
C5 C4 C3 C2 -179.9(2) . . . . ?
C1 O1 C9 C4 -1.1(3) . . . . ?
C1 O1 C9 C8 -179.7(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C15 S2 C7 C6 -46.5(2) . . . . ?
C15 S2 C7 C8 134.7(2) . . . . ?
C15 C10 C11 C12 -2.2(4) . . . . ?
C15 C14 C13 C12 -1.9(4) . . . . ?
C11 C10 C15 S2 179.83(17) . . . . ?
C11 C10 C15 C14 0.0(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?

_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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.624

