# Supplementary Information (SI) for CrystEngComm.
# 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_bpy
_database_code_depnum_ccdc_archive 'CCDC 2485302'
_audit_update_record             
;
2025-09-04 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-09-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 O3 S, C10 H9 N2'
_chemical_formula_sum            'C16 H13 N2 O3 S'
_chemical_formula_weight         313.34
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.3740(8)
_cell_length_b                   12.4855(13)
_cell_length_c                   15.6727(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.702(3)
_cell_angle_gamma                90
_cell_volume                     1407.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6600
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27622
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         2.106
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2560
_reflns_number_total             3241
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.041
_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)+(0.0472P)²+0.6014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C14(H14), C16(H16), N2(H2), C2(H2A), C3(H3), C5(H5), C7(H7),
  C9(H9), C11(H11), C13(H13), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.97023(6) 0.65238(3) 0.69327(3) 0.01770(13) Uani 1 1 d . . . . .
O1 O 1.15946(18) 0.63487(11) 0.74092(8) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.89697(19) 0.56742(10) 0.63185(8) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.84493(18) 0.67822(10) 0.75130(8) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.9932(2) 0.95133(14) 0.52670(10) 0.0173(4) Uani 1 1 d . . . . .
C6 C 0.9916(3) 0.95955(15) 0.61548(11) 0.0235(4) Uani 1 1 d . . . . .
H6 H 0.996383 1.028433 0.641621 0.028 Uiso 1 1 calc R U . . .
C8 C 0.9752(2) 0.76881(14) 0.62904(11) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.9833(3) 0.86970(15) 0.66619(11) 0.0223(4) Uani 1 1 d . . . . .
H10 H 0.983111 0.877300 0.726478 0.027 Uiso 1 1 calc R U . . .
C14 C 0.9833(3) 0.84921(15) 0.49052(12) 0.0244(4) Uani 1 1 d . . . . .
H14 H 0.982877 0.841098 0.430212 0.029 Uiso 1 1 calc R U . . .
C16 C 0.9740(3) 0.75916(15) 0.54098(12) 0.0234(4) Uani 1 1 d . . . . .
H16 H 0.966660 0.690165 0.514887 0.028 Uiso 1 1 calc R U . . .
N1 N 0.4972(2) 0.73690(13) 0.58255(10) 0.0258(4) Uani 1 1 d . . . . .
N2 N 0.5236(2) 0.56338(12) 0.68585(9) 0.0205(3) Uani 1 1 d . . . . .
H2 H 0.600841 0.617943 0.696593 0.025 Uiso 1 1 calc R U . . .
C2 C 0.5341(3) 0.48769(16) 0.74727(12) 0.0252(4) Uani 1 1 d . . . . .
H2A H 0.624117 0.493587 0.800678 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2800(3) 0.47386(16) 0.59199(12) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.192475 0.468880 0.537721 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4061(3) 0.64921(15) 0.54690(12) 0.0211(4) Uani 1 1 d . . . . .
C5 C 0.4155(3) 0.40173(16) 0.73349(12) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.421376 0.348052 0.776970 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3310(3) 0.72711(17) 0.40513(13) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.274450 0.723919 0.344552 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3226(3) 0.64052(16) 0.45860(12) 0.0260(4) Uani 1 1 d . . . . .
H9 H 0.261271 0.576428 0.435677 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2872(3) 0.39511(17) 0.65466(13) 0.0284(4) Uani 1 1 d . . . . .
H11 H 0.203632 0.336247 0.643576 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4008(3) 0.55996(15) 0.60859(11) 0.0199(4) Uani 1 1 d . . . . .
C13 C 0.4224(3) 0.81845(18) 0.44067(13) 0.0313(5) Uani 1 1 d . . . . .
H13 H 0.428948 0.879489 0.405289 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5045(3) 0.81926(17) 0.52924(14) 0.0319(5) Uani 1 1 d . . . . .
H15 H 0.569523 0.881855 0.553207 0.038 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 1.4471(14) . ?
S1 O2 1.4544(13) . ?
S1 O3 1.4678(13) . ?
S1 C8 1.7733(18) . ?
C1 C1 1.491(3) 3_776 ?
C1 C6 1.398(2) . ?
C1 C14 1.391(3) . ?
C6 H6 0.9500 . ?
C6 C10 1.384(3) . ?
C8 C10 1.384(2) . ?
C8 C16 1.383(2) . ?
C10 H10 0.9500 . ?
C14 H14 0.9500 . ?
C14 C16 1.385(3) . ?
C16 H16 0.9500 . ?
N1 C4 1.341(2) . ?
N1 C15 1.334(3) . ?
N2 H2 0.8800 . ?
N2 C2 1.339(2) . ?
N2 C12 1.344(2) . ?
C2 H2A 0.9500 . ?
C2 C5 1.371(3) . ?
C3 H3 0.9500 . ?
C3 C11 1.383(3) . ?
C3 C12 1.384(3) . ?
C4 C9 1.390(3) . ?
C4 C12 1.481(3) . ?
C5 H5 0.9500 . ?
C5 C11 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C9 1.378(3) . ?
C7 C13 1.378(3) . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C13 C15 1.387(3) . ?
C15 H15 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 O2 114.02(8) . . ?
O1 S1 O3 112.36(8) . . ?
O1 S1 C8 106.18(8) . . ?
O2 S1 O3 112.19(8) . . ?
O2 S1 C8 105.85(8) . . ?
O3 S1 C8 105.43(8) . . ?
C6 C1 C1 121.0(2) . 3_776 ?
C14 C1 C1 121.48(18) . 3_776 ?
C14 C1 C6 117.51(16) . . ?
C1 C6 H6 119.2 . . ?
C10 C6 C1 121.55(17) . . ?
C10 C6 H6 119.2 . . ?
C10 C8 S1 120.79(13) . . ?
C16 C8 S1 119.91(14) . . ?
C16 C8 C10 119.30(16) . . ?
C6 C10 H10 120.0 . . ?
C8 C10 C6 119.97(16) . . ?
C8 C10 H10 120.0 . . ?
C1 C14 H14 119.5 . . ?
C16 C14 C1 121.08(16) . . ?
C16 C14 H14 119.5 . . ?
C8 C16 C14 120.57(17) . . ?
C8 C16 H16 119.7 . . ?
C14 C16 H16 119.7 . . ?
C15 N1 C4 117.02(17) . . ?
C2 N2 H2 118.4 . . ?
C2 N2 C12 123.10(17) . . ?
C12 N2 H2 118.4 . . ?
N2 C2 H2A 119.8 . . ?
N2 C2 C5 120.35(18) . . ?
C5 C2 H2A 119.8 . . ?
C11 C3 H3 120.1 . . ?
C11 C3 C12 119.77(18) . . ?
C12 C3 H3 120.1 . . ?
N1 C4 C9 123.40(18) . . ?
N1 C4 C12 115.15(16) . . ?
C9 C4 C12 121.45(17) . . ?
C2 C5 H5 120.8 . . ?
C2 C5 C11 118.34(18) . . ?
C11 C5 H5 120.8 . . ?
C9 C7 H7 120.4 . . ?
C9 C7 C13 119.13(18) . . ?
C13 C7 H7 120.4 . . ?
C4 C9 H9 120.8 . . ?
C7 C9 C4 118.38(19) . . ?
C7 C9 H9 120.8 . . ?
C3 C11 C5 120.23(19) . . ?
C3 C11 H11 119.9 . . ?
C5 C11 H11 119.9 . . ?
N2 C12 C3 118.20(17) . . ?
N2 C12 C4 117.06(16) . . ?
C3 C12 C4 124.74(17) . . ?
C7 C13 H13 120.7 . . ?
C7 C13 C15 118.53(19) . . ?
C15 C13 H13 120.7 . . ?
N1 C15 C13 123.5(2) . . ?
N1 C15 H15 118.2 . . ?
C13 C15 H15 118.2 . . ?

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
S1 C8 C10 C6 178.44(16) . . . . ?
S1 C8 C16 C14 -178.12(16) . . . . ?
O1 S1 C8 C10 -78.14(17) . . . . ?
O1 S1 C8 C16 100.86(17) . . . . ?
O2 S1 C8 C10 160.33(15) . . . . ?
O2 S1 C8 C16 -20.67(18) . . . . ?
O3 S1 C8 C10 41.27(17) . . . . ?
O3 S1 C8 C16 -139.73(16) . . . . ?
C1 C1 C6 C10 -178.5(2) 3_776 . . . ?
C1 C1 C14 C16 178.9(2) 3_776 . . . ?
C1 C6 C10 C8 -0.4(3) . . . . ?
C1 C14 C16 C8 -0.3(3) . . . . ?
C6 C1 C14 C16 -0.6(3) . . . . ?
C10 C8 C16 C14 0.9(3) . . . . ?
C14 C1 C6 C10 0.9(3) . . . . ?
C16 C8 C10 C6 -0.6(3) . . . . ?
N1 C4 C9 C7 -1.2(3) . . . . ?
N1 C4 C12 N2 -16.8(2) . . . . ?
N1 C4 C12 C3 163.57(19) . . . . ?
N2 C2 C5 C11 0.6(3) . . . . ?
C2 N2 C12 C3 -0.1(3) . . . . ?
C2 N2 C12 C4 -179.74(17) . . . . ?
C2 C5 C11 C3 -0.1(3) . . . . ?
C4 N1 C15 C13 0.6(3) . . . . ?
C7 C13 C15 N1 -1.3(4) . . . . ?
C9 C4 C12 N2 162.77(18) . . . . ?
C9 C4 C12 C3 -16.8(3) . . . . ?
C9 C7 C13 C15 0.7(3) . . . . ?
C11 C3 C12 N2 0.6(3) . . . . ?
C11 C3 C12 C4 -179.79(18) . . . . ?
C12 N2 C2 C5 -0.5(3) . . . . ?
C12 C3 C11 C5 -0.5(3) . . . . ?
C12 C4 C9 C7 179.24(18) . . . . ?
C13 C7 C9 C4 0.5(3) . . . . ?
C15 N1 C4 C9 0.6(3) . . . . ?
C15 N1 C4 C12 -179.76(18) . . . . ?

_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_bpdoz
_database_code_depnum_ccdc_archive 'CCDC 2485304'
_audit_update_record             
;
2025-09-04 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-09-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 O6 S2, H2 O, C12 H10 N4 O'
_chemical_formula_sum            'C24 H20 N4 O8 S2'
_chemical_formula_weight         556.56
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.8117(9)
_cell_length_b                   13.3456(14)
_cell_length_c                   22.478(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2343.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3417
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7330
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0865 after correction.
The Ratio of minimum to maximum transmission is 0.8896.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1390
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            42532
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.369
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3991
_reflns_number_total             4802
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4802
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.046
_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)+(0.0384P)²+1.2039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1B,H1C)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C14(H14), C17(H17), C18(H18), C20(H20),
 N1(H1A), N2(H2A), C5(H5), C7(H7), C11(H11), C15(H15), C19(H19), C21(H21),
 C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.02092(14) 0.40730(9) 0.98270(5) 0.0273(3) Uani 1 1 d . . . . .
S2 S 0.98099(15) 0.33424(9) 0.65183(5) 0.0274(3) Uani 1 1 d . . . . .
O2 O -0.0139(5) 0.5135(2) 0.98802(16) 0.0422(9) Uani 1 1 d . . . . .
O3 O -0.1254(4) 0.3492(3) 0.96383(16) 0.0427(9) Uani 1 1 d . . . . .
O4 O 0.1007(4) 0.3665(3) 1.03647(15) 0.0376(9) Uani 1 1 d . . . . .
O5 O 0.9192(5) 0.3748(4) 0.59606(17) 0.0599(13) Uani 1 1 d . . . . .
O6 O 1.1352(5) 0.3817(3) 0.67215(17) 0.0509(11) Uani 1 1 d . . . . .
O7 O 0.9914(5) 0.2267(2) 0.65164(19) 0.0495(10) Uani 1 1 d . . . . .
C1 C 0.1528(6) 0.4437(3) 0.8719(2) 0.0255(10) Uani 1 1 d . . . . .
H1 H 0.050799 0.480700 0.865129 0.031 Uiso 1 1 calc R U . . .
C2 C 0.8620(6) 0.3608(3) 0.7649(2) 0.0270(10) Uani 1 1 d . . . . .
H2 H 0.978122 0.352721 0.776572 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4520(6) 0.3380(3) 0.8919(2) 0.0287(11) Uani 1 1 d . . . . .
H3 H 0.554922 0.302256 0.899420 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4284(5) 0.3858(3) 0.8369(2) 0.0232(10) Uani 1 1 d . . . . .
C6 C 0.5650(5) 0.3812(3) 0.7912(2) 0.0234(10) Uani 1 1 d . . . . .
C9 C 0.7359(6) 0.3706(4) 0.8076(2) 0.0286(11) Uani 1 1 d . . . . .
H9 H 0.766121 0.370195 0.848580 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8193(6) 0.3625(3) 0.7049(2) 0.0233(10) Uani 1 1 d . . . . .
C14 C 0.2747(6) 0.4368(3) 0.8276(2) 0.0257(10) Uani 1 1 d . . . . .
H14 H 0.253590 0.467182 0.790066 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3259(6) 0.3424(3) 0.9354(2) 0.0283(10) Uani 1 1 d . . . . .
H17 H 0.341737 0.307562 0.971854 0.034 Uiso 1 1 calc R U . . .
C18 C 0.6512(6) 0.3764(3) 0.6877(2) 0.0256(10) Uani 1 1 d . . . . .
H18 H 0.622764 0.379927 0.646670 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5234(6) 0.3852(3) 0.73063(19) 0.0258(9) Uani 1 1 d . . . . .
H20 H 0.407621 0.393945 0.718772 0.031 Uiso 1 1 calc R U . . .
C24 C 0.1783(5) 0.3968(3) 0.92644(19) 0.0225(9) Uani 1 1 d . . . . .
O1 O 0.1580(6) 0.6426(3) 1.0657(2) 0.0587(12) Uani 1 1 d G . . . .
H1B H 0.097673 0.593624 1.051086 0.088 Uiso 1 1 d G U . . .
H1C H 0.226351 0.614118 1.091082 0.088 Uiso 1 1 d G U . . .
O8 O 0.7769(4) 0.3725(2) 0.27417(13) 0.0257(7) Uani 1 1 d . . . . .
N1 N 1.0074(6) 0.3616(3) 0.48102(17) 0.0342(9) Uani 1 1 d . . . . .
H1A H 1.023685 0.361297 0.519758 0.041 Uiso 1 1 calc R U . . .
N2 N 0.4051(5) 0.3788(3) 0.09391(18) 0.0299(9) Uani 1 1 d . . . . .
H2A H 0.320570 0.378878 0.068053 0.036 Uiso 1 1 calc R U . . .
N3 N 0.9709(5) 0.3663(3) 0.20295(16) 0.0273(8) Uani 1 1 d . . . . .
N4 N 1.0540(5) 0.3626(3) 0.25804(17) 0.0263(9) Uani 1 1 d . . . . .
C5 C 0.8506(7) 0.3792(4) 0.4608(2) 0.0337(12) Uani 1 1 d . . . . .
H5 H 0.759363 0.390586 0.487935 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7004(6) 0.3808(4) 0.1123(2) 0.0308(11) Uani 1 1 d . . . . .
H7 H 0.814844 0.382994 0.098099 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6663(6) 0.3760(3) 0.1732(2) 0.0244(10) Uani 1 1 d . . . . .
C10 C 0.8083(6) 0.3719(3) 0.2150(2) 0.0247(10) Uani 1 1 d . . . . .
C11 C 1.1413(7) 0.3445(4) 0.4459(2) 0.0348(12) Uani 1 1 d . . . . .
H11 H 1.250594 0.330926 0.462572 0.042 Uiso 1 1 calc R U . . .
C13 C 0.9561(6) 0.3647(3) 0.36236(19) 0.0238(10) Uani 1 1 d . . . . .
C15 C 0.4971(7) 0.3735(3) 0.1930(2) 0.0307(10) Uani 1 1 d . . . . .
H15 H 0.471917 0.370371 0.234287 0.037 Uiso 1 1 calc R U . . .
C16 C 0.9356(6) 0.3664(3) 0.2976(2) 0.0248(10) Uani 1 1 d . . . . .
C19 C 0.3680(6) 0.3754(4) 0.1518(2) 0.0321(11) Uani 1 1 d . . . . .
H19 H 0.252008 0.374440 0.164499 0.038 Uiso 1 1 calc R U . . .
C21 C 0.8204(6) 0.3808(4) 0.4009(2) 0.0295(11) Uani 1 1 d . . . . .
H21 H 0.708544 0.392828 0.385916 0.035 Uiso 1 1 calc R U . . .
C22 C 1.1200(6) 0.3465(3) 0.3856(2) 0.0280(11) Uani 1 1 d . . . . .
H22 H 1.214610 0.335876 0.359780 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5656(6) 0.3821(4) 0.0738(2) 0.0342(12) Uani 1 1 d . . . . .
H23 H 0.586259 0.385323 0.032145 0.041 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 O2 1.448(3) . ?
S1 O3 1.445(4) . ?
S1 O4 1.465(3) . ?
S1 C24 1.769(4) . ?
S2 O5 1.448(4) . ?
S2 O6 1.435(4) . ?
S2 O7 1.438(3) . ?
S2 C12 1.778(5) . ?
C1 H1 0.9500 . ?
C1 C14 1.382(6) . ?
C1 C24 1.390(6) . ?
C2 H2 0.9500 . ?
C2 C9 1.382(6) . ?
C2 C12 1.390(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(6) . ?
C3 C17 1.390(6) . ?
C4 C6 1.483(6) . ?
C4 C14 1.396(6) . ?
C6 C9 1.392(6) . ?
C6 C20 1.401(6) . ?
C9 H9 0.9500 . ?
C12 C18 1.381(6) . ?
C14 H14 0.9500 . ?
C17 H17 0.9500 . ?
C17 C24 1.377(6) . ?
C18 H18 0.9500 . ?
C18 C20 1.394(6) . ?
C20 H20 0.9500 . ?
O1 H1B 0.8701 . ?
O1 H1C 0.8701 . ?
O8 C10 1.354(5) . ?
O8 C16 1.349(5) . ?
N1 H1A 0.8800 . ?
N1 C5 1.328(6) . ?
N1 C11 1.330(6) . ?
N2 H2A 0.8800 . ?
N2 C19 1.335(6) . ?
N2 C23 1.334(6) . ?
N3 N4 1.399(5) . ?
N3 C10 1.300(6) . ?
N4 C16 1.284(6) . ?
C5 H5 0.9500 . ?
C5 C21 1.368(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.396(6) . ?
C7 C23 1.364(6) . ?
C8 C10 1.454(6) . ?
C8 C15 1.395(7) . ?
C11 H11 0.9500 . ?
C11 C22 1.366(7) . ?
C13 C16 1.465(6) . ?
C13 C21 1.385(6) . ?
C13 C22 1.404(6) . ?
C15 H15 0.9500 . ?
C15 C19 1.369(7) . ?
C19 H19 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 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
O2 S1 O4 112.0(2) . . ?
O2 S1 C24 105.5(2) . . ?
O3 S1 O2 113.6(2) . . ?
O3 S1 O4 112.3(2) . . ?
O3 S1 C24 107.3(2) . . ?
O4 S1 C24 105.4(2) . . ?
O5 S2 C12 105.3(2) . . ?
O6 S2 O5 113.0(3) . . ?
O6 S2 O7 113.2(3) . . ?
O6 S2 C12 106.8(2) . . ?
O7 S2 O5 112.9(3) . . ?
O7 S2 C12 104.7(2) . . ?
C14 C1 H1 119.8 . . ?
C14 C1 C24 120.5(4) . . ?
C24 C1 H1 119.8 . . ?
C9 C2 H2 119.9 . . ?
C9 C2 C12 120.1(4) . . ?
C12 C2 H2 119.9 . . ?
C4 C3 H3 119.7 . . ?
C17 C3 H3 119.7 . . ?
C17 C3 C4 120.5(4) . . ?
C3 C4 C6 119.8(4) . . ?
C14 C4 C3 117.9(4) . . ?
C14 C4 C6 122.3(4) . . ?
C9 C6 C4 120.7(4) . . ?
C9 C6 C20 118.9(4) . . ?
C20 C6 C4 120.3(4) . . ?
C2 C9 C6 120.6(4) . . ?
C2 C9 H9 119.7 . . ?
C6 C9 H9 119.7 . . ?
C2 C12 S2 118.5(4) . . ?
C18 C12 S2 121.1(3) . . ?
C18 C12 C2 120.1(4) . . ?
C1 C14 C4 121.1(4) . . ?
C1 C14 H14 119.5 . . ?
C4 C14 H14 119.5 . . ?
C3 C17 H17 119.6 . . ?
C24 C17 C3 120.9(4) . . ?
C24 C17 H17 119.6 . . ?
C12 C18 H18 120.0 . . ?
C12 C18 C20 119.9(4) . . ?
C20 C18 H18 120.0 . . ?
C6 C20 H20 119.9 . . ?
C18 C20 C6 120.2(4) . . ?
C18 C20 H20 119.9 . . ?
C1 C24 S1 119.7(4) . . ?
C17 C24 S1 121.3(3) . . ?
C17 C24 C1 119.1(4) . . ?
H1B O1 H1C 104.5 . . ?
C16 O8 C10 102.5(3) . . ?
C5 N1 H1A 118.2 . . ?
C5 N1 C11 123.6(4) . . ?
C11 N1 H1A 118.2 . . ?
C19 N2 H2A 118.8 . . ?
C23 N2 H2A 118.8 . . ?
C23 N2 C19 122.5(4) . . ?
C10 N3 N4 105.8(4) . . ?
C16 N4 N3 106.1(3) . . ?
N1 C5 H5 120.0 . . ?
N1 C5 C21 119.9(5) . . ?
C21 C5 H5 120.0 . . ?
C8 C7 H7 120.8 . . ?
C23 C7 H7 120.8 . . ?
C23 C7 C8 118.5(4) . . ?
C7 C8 C10 119.2(4) . . ?
C15 C8 C7 119.6(4) . . ?
C15 C8 C10 121.1(4) . . ?
O8 C10 C8 119.7(4) . . ?
N3 C10 O8 112.4(4) . . ?
N3 C10 C8 127.8(4) . . ?
N1 C11 H11 120.3 . . ?
N1 C11 C22 119.3(5) . . ?
C22 C11 H11 120.3 . . ?
C21 C13 C16 122.3(4) . . ?
C21 C13 C22 119.5(4) . . ?
C22 C13 C16 118.2(4) . . ?
C8 C15 H15 120.6 . . ?
C19 C15 C8 118.8(4) . . ?
C19 C15 H15 120.6 . . ?
O8 C16 C13 119.3(4) . . ?
N4 C16 O8 113.2(4) . . ?
N4 C16 C13 127.5(4) . . ?
N2 C19 C15 120.0(4) . . ?
N2 C19 H19 120.0 . . ?
C15 C19 H19 120.0 . . ?
C5 C21 C13 118.8(4) . . ?
C5 C21 H21 120.6 . . ?
C13 C21 H21 120.6 . . ?
C11 C22 C13 118.9(5) . . ?
C11 C22 H22 120.5 . . ?
C13 C22 H22 120.5 . . ?
N2 C23 C7 120.6(4) . . ?
N2 C23 H23 119.7 . . ?
C7 C23 H23 119.7 . . ?

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 C12 C18 C20 171.4(3) . . . . ?
O2 S1 C24 C1 -51.0(4) . . . . ?
O2 S1 C24 C17 129.3(4) . . . . ?
O3 S1 C24 C1 70.5(4) . . . . ?
O3 S1 C24 C17 -109.2(4) . . . . ?
O4 S1 C24 C1 -169.7(4) . . . . ?
O4 S1 C24 C17 10.6(4) . . . . ?
O5 S2 C12 C2 -160.8(4) . . . . ?
O5 S2 C12 C18 25.5(5) . . . . ?
O6 S2 C12 C2 -40.4(4) . . . . ?
O6 S2 C12 C18 145.8(4) . . . . ?
O7 S2 C12 C2 79.9(4) . . . . ?
O7 S2 C12 C18 -93.8(4) . . . . ?
C2 C12 C18 C20 -2.2(7) . . . . ?
C3 C4 C6 C9 -27.9(6) . . . . ?
C3 C4 C6 C20 150.6(4) . . . . ?
C3 C4 C14 C1 2.8(7) . . . . ?
C3 C17 C24 S1 -177.3(3) . . . . ?
C3 C17 C24 C1 3.0(7) . . . . ?
C4 C3 C17 C24 -2.4(7) . . . . ?
C4 C6 C9 C2 176.4(4) . . . . ?
C4 C6 C20 C18 -177.1(4) . . . . ?
C6 C4 C14 C1 -177.0(4) . . . . ?
C9 C2 C12 S2 -172.4(4) . . . . ?
C9 C2 C12 C18 1.4(7) . . . . ?
C9 C6 C20 C18 1.4(7) . . . . ?
C12 C2 C9 C6 0.8(7) . . . . ?
C12 C18 C20 C6 0.8(6) . . . . ?
C14 C1 C24 S1 179.6(3) . . . . ?
C14 C1 C24 C17 -0.7(7) . . . . ?
C14 C4 C6 C9 152.0(5) . . . . ?
C14 C4 C6 C20 -29.5(6) . . . . ?
C17 C3 C4 C6 179.3(4) . . . . ?
C17 C3 C4 C14 -0.5(7) . . . . ?
C20 C6 C9 C2 -2.2(7) . . . . ?
C24 C1 C14 C4 -2.3(7) . . . . ?
N1 C5 C21 C13 -0.5(7) . . . . ?
N1 C11 C22 C13 -1.3(7) . . . . ?
N3 N4 C16 O8 0.0(5) . . . . ?
N3 N4 C16 C13 179.9(4) . . . . ?
N4 N3 C10 O8 0.3(5) . . . . ?
N4 N3 C10 C8 -179.1(4) . . . . ?
C5 N1 C11 C22 1.3(8) . . . . ?
C7 C8 C10 O8 176.6(4) . . . . ?
C7 C8 C10 N3 -4.1(8) . . . . ?
C7 C8 C15 C19 0.1(7) . . . . ?
C8 C7 C23 N2 -0.1(8) . . . . ?
C8 C15 C19 N2 0.6(7) . . . . ?
C10 O8 C16 N4 0.2(5) . . . . ?
C10 O8 C16 C13 -179.8(4) . . . . ?
C10 N3 N4 C16 -0.1(5) . . . . ?
C10 C8 C15 C19 -178.6(5) . . . . ?
C11 N1 C5 C21 -0.4(8) . . . . ?
C15 C8 C10 O8 -4.7(7) . . . . ?
C15 C8 C10 N3 174.6(5) . . . . ?
C16 O8 C10 N3 -0.3(5) . . . . ?
C16 O8 C10 C8 179.1(4) . . . . ?
C16 C13 C21 C5 -179.2(4) . . . . ?
C16 C13 C22 C11 -179.9(4) . . . . ?
C19 N2 C23 C7 0.9(8) . . . . ?
C21 C13 C16 O8 -7.7(7) . . . . ?
C21 C13 C16 N4 172.3(5) . . . . ?
C21 C13 C22 C11 0.5(7) . . . . ?
C22 C13 C16 O8 172.7(4) . . . . ?
C22 C13 C16 N4 -7.3(7) . . . . ?
C22 C13 C21 C5 0.4(7) . . . . ?
C23 N2 C19 C15 -1.2(8) . . . . ?
C23 C7 C8 C10 178.4(5) . . . . ?
C23 C7 C8 C15 -0.4(8) . . . . ?

_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_bpee
_database_code_depnum_ccdc_archive 'CCDC 2485303'
_audit_update_record             
;
2025-09-04 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-09-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 O6 S2, 2(H2 O), C12 H12 N2'
_chemical_formula_sum            'C24 H24 N2 O8 S2'
_chemical_formula_weight         532.57
_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                   7.2167(8)
_cell_length_b                   15.0373(18)
_cell_length_c                   11.0377(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.978(4)
_cell_angle_gamma                90
_cell_volume                     1197.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4003
_cell_measurement_temperature    122.00
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1472
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21458
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.763
_diffrn_reflns_theta_min         2.289
_diffrn_ambient_temperature      122.00
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1960
_reflns_number_total             2544
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+2.1938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1496
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), N1(H1), C7(H7), C8(H8), C10(H10), C11(H11),
 C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.70130(10) 0.77595(4) 0.15247(6) 0.0177(2) Uani 1 1 d . . . . .
O1 O 0.7971(4) 0.70357(17) 0.2117(2) 0.0426(7) Uani 1 1 d . . . . .
O2 O 0.5284(3) 0.74777(16) 0.0930(2) 0.0356(6) Uani 1 1 d . . . . .
O3 O 0.8170(3) 0.82578(15) 0.0710(2) 0.0305(6) Uani 1 1 d . . . . .
C1 C 0.5277(3) 0.96831(17) 0.4516(2) 0.0136(6) Uani 1 1 d . . . . .
C2 C 0.6368(4) 0.85025(18) 0.2691(2) 0.0156(6) Uani 1 1 d . . . . .
C3 C 0.6234(4) 0.94081(18) 0.2451(2) 0.0166(6) Uani 1 1 d . . . . .
H3 H 0.651456 0.962913 0.166850 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5402(4) 0.87695(19) 0.4732(3) 0.0207(6) Uani 1 1 d . . . . .
H4 H 0.511441 0.854431 0.551082 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5690(4) 0.99875(18) 0.3354(3) 0.0171(6) Uani 1 1 d . . . . .
H5 H 0.559598 1.060479 0.318057 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5937(4) 0.81871(19) 0.3834(3) 0.0220(6) Uani 1 1 d . . . . .
H6 H 0.601050 0.756809 0.400003 0.026 Uiso 1 1 calc R U . . .
O4 O 0.3953(4) 0.87310(16) -0.0720(2) 0.0299(6) Uani 1 1 d . . . . .
H4A H 0.437(6) 0.835(3) -0.032(4) 0.045 Uiso 1 1 d . U . . .
H4B H 0.377(6) 0.853(3) -0.130(4) 0.045 Uiso 1 1 d . U . . .
N1 N 1.2036(4) 0.93675(19) 0.1148(2) 0.0267(6) Uani 1 1 d . . . . .
H1 H 1.246860 0.920145 0.044245 0.032 Uiso 1 1 calc R U . . .
C7 C 1.1144(4) 0.9002(2) 0.3126(3) 0.0301(8) Uani 1 1 d . . . . .
H7 H 1.097677 0.857005 0.374218 0.036 Uiso 1 1 calc R U . . .
C8 C 1.1800(4) 0.8755(2) 0.2010(3) 0.0286(7) Uani 1 1 d . . . . .
H8 H 1.208444 0.814941 0.185280 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0727(4) 0.9898(2) 0.3341(3) 0.0297(7) Uani 1 1 d . . . . .
C10 C 1.1634(4) 1.0225(2) 0.1326(3) 0.0308(8) Uani 1 1 d . . . . .
H10 H 1.181573 1.064146 0.069265 0.037 Uiso 1 1 calc R U . . .
C11 C 1.0967(5) 1.0507(2) 0.2404(3) 0.0322(8) Uani 1 1 d . . . . .
H11 H 1.066617 1.111564 0.251892 0.039 Uiso 1 1 calc R U . . .
C12 C 1.0056(4) 1.0242(2) 0.4514(3) 0.0300(8) Uani 1 1 d . . . . .
H12 H 0.968933 1.084764 0.455648 0.036 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 1.440(2) . ?
S1 O2 1.463(2) . ?
S1 O3 1.447(2) . ?
S1 C2 1.773(3) . ?
C1 C1 1.492(5) 3_676 ?
C1 C4 1.397(4) . ?
C1 C5 1.398(4) . ?
C2 C3 1.391(4) . ?
C2 C6 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O4 H4A 0.78(5) . ?
O4 H4B 0.71(5) . ?
N1 H1 0.8800 . ?
N1 C8 1.337(4) . ?
N1 C10 1.337(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(5) . ?
C7 C9 1.401(5) . ?
C8 H8 0.9500 . ?
C9 C11 1.394(5) . ?
C9 C12 1.483(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.359(5) . ?
C11 H11 0.9500 . ?
C12 C12 1.301(7) 3_776 ?
C12 H12 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 O2 112.57(17) . . ?
O1 S1 O3 113.33(16) . . ?
O1 S1 C2 106.04(13) . . ?
O2 S1 C2 106.02(14) . . ?
O3 S1 O2 111.60(15) . . ?
O3 S1 C2 106.66(13) . . ?
C4 C1 C1 121.5(3) . 3_676 ?
C4 C1 C5 117.7(2) . . ?
C5 C1 C1 120.8(3) . 3_676 ?
C3 C2 S1 119.8(2) . . ?
C6 C2 S1 120.7(2) . . ?
C6 C2 C3 119.5(2) . . ?
C2 C3 H3 120.1 . . ?
C5 C3 C2 119.8(2) . . ?
C5 C3 H3 120.1 . . ?
C1 C4 H4 119.4 . . ?
C6 C4 C1 121.2(3) . . ?
C6 C4 H4 119.4 . . ?
C1 C5 H5 119.3 . . ?
C3 C5 C1 121.4(2) . . ?
C3 C5 H5 119.3 . . ?
C2 C6 H6 119.8 . . ?
C4 C6 C2 120.3(3) . . ?
C4 C6 H6 119.8 . . ?
H4A O4 H4B 105(5) . . ?
C8 N1 H1 119.0 . . ?
C8 N1 C10 121.9(3) . . ?
C10 N1 H1 119.0 . . ?
C8 C7 H7 120.4 . . ?
C8 C7 C9 119.3(3) . . ?
C9 C7 H7 120.4 . . ?
N1 C8 C7 120.0(3) . . ?
N1 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C9 C12 123.9(3) . . ?
C11 C9 C7 118.4(3) . . ?
C11 C9 C12 117.7(3) . . ?
N1 C10 H10 119.6 . . ?
N1 C10 C11 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C11 H11 120.2 . . ?
C10 C11 C9 119.7(3) . . ?
C10 C11 H11 120.2 . . ?
C9 C12 H12 118.3 . . ?
C12 C12 C9 123.5(4) 3_776 . ?
C12 C12 H12 118.3 3_776 . ?

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 C2 C3 C5 178.6(2) . . . . ?
S1 C2 C6 C4 -178.8(2) . . . . ?
O1 S1 C2 C3 149.8(2) . . . . ?
O1 S1 C2 C6 -32.3(3) . . . . ?
O2 S1 C2 C3 -90.3(3) . . . . ?
O2 S1 C2 C6 87.6(3) . . . . ?
O3 S1 C2 C3 28.7(3) . . . . ?
O3 S1 C2 C6 -153.4(2) . . . . ?
C1 C1 C4 C6 -179.3(3) 3_676 . . . ?
C1 C1 C5 C3 179.0(3) 3_676 . . . ?
C1 C4 C6 C2 0.2(5) . . . . ?
C2 C3 C5 C1 0.3(4) . . . . ?
C3 C2 C6 C4 -0.9(4) . . . . ?
C4 C1 C5 C3 -1.0(4) . . . . ?
C5 C1 C4 C6 0.8(4) . . . . ?
C6 C2 C3 C5 0.6(4) . . . . ?
N1 C10 C11 C9 1.0(5) . . . . ?
C7 C9 C11 C10 -1.6(5) . . . . ?
C7 C9 C12 C12 6.2(6) . . . 3_776 ?
C8 N1 C10 C11 0.2(5) . . . . ?
C8 C7 C9 C11 1.0(5) . . . . ?
C8 C7 C9 C12 -178.5(3) . . . . ?
C9 C7 C8 N1 0.1(5) . . . . ?
C10 N1 C8 C7 -0.7(5) . . . . ?
C11 C9 C12 C12 -173.3(4) . . . 3_776 ?
C12 C9 C11 C10 178.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT417_bpee                
;
PROBLEM: Short Inter D-H..H-D       H1       ..H4A      .       2.07 Ang.  
RESPONSE: The reason for this alarm is attributed to the strong 
hydrogen bonding interaction in the organic salt.
;
# end Validation Reply Form
