# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_241225_BTBQ
_audit_block_doi                 10.5517/ccdc.csd.cc2pllzw
_database_code_depnum_ccdc_archive 'CCDC 2490539'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2025-09-23 deposited with the CCDC.	2026-04-23 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H7 N O2 S'
_chemical_formula_moiety         'C13 H7 N O2 S'
_chemical_formula_weight         241.26
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.4317(6)
_cell_length_b                   10.6512(7)
_cell_length_c                   11.5830(8)
_cell_angle_alpha                85.382(6)
_cell_angle_beta                 89.672(6)
_cell_angle_gamma                89.998(6)
_cell_volume                     1036.85(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4018
_cell_measurement_theta_min      3.83
_cell_measurement_theta_max      68.17
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496.00
_exptl_absorpt_coefficient_mu    2.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_T_max  0.766

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            10927
_diffrn_reflns_av_unetI/netI     0.3616
_diffrn_reflns_av_R_equivalents  0.1284
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_min         3.829
_diffrn_reflns_theta_full        68.250
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3703
_reflns_number_gt                1197
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2023
_refine_ls_R_factor_gt           0.1018
_refine_ls_wR_factor_ref         0.3386
_refine_ls_wR_factor_gt          0.2301
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1729P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.86
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.0291(3) 0.82334(19) 0.37306(19) 0.0472(7) Uani 1 1 d . . .
O1 O -0.1668(7) 0.7269(5) 0.5563(5) 0.0521(17) Uani 1 1 d . . .
O2 O 0.1753(7) 0.8677(5) 0.9069(5) 0.0501(17) Uani 1 1 d . . .
N1 N 0.2456(8) 0.9400(6) 0.4825(6) 0.0446(19) Uani 1 1 d . . .
C1 C 0.1170(10) 0.8703(7) 0.4987(6) 0.039(2) Uani 1 1 d . . .
C2 C 0.1740(9) 0.9044(7) 0.2932(7) 0.038(2) Uani 1 1 d . . .
C3 C 0.1981(10) 0.9152(7) 0.1712(7) 0.048(2) Uani 1 1 d . . .
H3 H 0.1284 0.8769 0.1229 0.058 Uiso 1 1 calc R . .
C4 C 0.3233(10) 0.9818(7) 0.1263(6) 0.038(2) Uani 1 1 d . . .
H4 H 0.3379 0.9900 0.0464 0.046 Uiso 1 1 calc R . .
C5 C 0.4323(10) 1.0388(7) 0.1969(7) 0.044(2) Uani 1 1 d . . .
H5 H 0.5197 1.0821 0.1645 0.052 Uiso 1 1 calc R . .
C6 C 0.4071(10) 1.0293(7) 0.3160(8) 0.051(3) Uani 1 1 d . . .
H6 H 0.4764 1.0705 0.3625 0.061 Uiso 1 1 calc R . .
C7 C 0.2819(10) 0.9605(7) 0.3685(7) 0.035(2) Uani 1 1 d . . .
C8 C 0.0637(9) 0.8361(7) 0.6145(8) 0.038(2) Uani 1 1 d . . .
C9 C 0.1400(10) 0.8734(7) 0.7079(7) 0.043(2) Uani 1 1 d . . .
H9 H 0.2282 0.9251 0.6951 0.052 Uiso 1 1 calc R . .
C10 C 0.0935(11) 0.8383(7) 0.8274(8) 0.042(2) Uani 1 1 d . . .
C11 C -0.0593(10) 0.7714(8) 0.8477(7) 0.044(2) Uani 1 1 d . . .
H11 H -0.0987 0.7549 0.9226 0.053 Uiso 1 1 calc R . .
C12 C -0.1406(11) 0.7347(8) 0.7563(9) 0.059(3) Uani 1 1 d . . .
H12 H -0.2332 0.6882 0.7701 0.071 Uiso 1 1 calc R . .
C13 C -0.0906(10) 0.7640(8) 0.6397(8) 0.043(2) Uani 1 1 d . . .
S2 S 0.7960(3) 0.4550(2) 0.0258(2) 0.0538(8) Uani 1 1 d . . .
O3 O 0.7339(7) 0.4141(5) -0.2084(5) 0.0563(18) Uani 1 1 d . . .
O4 O 0.1868(7) 0.1689(5) -0.1452(6) 0.067(2) Uani 1 1 d . . .
N2 N 0.5477(9) 0.3552(6) 0.1324(7) 0.051(2) Uani 1 1 d . . .
C14 C 0.5401(11) 0.3286(7) -0.0725(8) 0.045(2) Uani 1 1 d . . .
C15 C 0.7809(11) 0.4619(8) 0.1731(9) 0.055(3) Uani 1 1 d . . .
C16 C 0.8853(11) 0.5160(8) 0.2536(8) 0.050(3) Uani 1 1 d . . .
H16 H 0.9777 0.5567 0.2270 0.060 Uiso 1 1 calc R . .
C17 C 0.8501(12) 0.5080(8) 0.3647(10) 0.066(3) Uani 1 1 d . . .
H17 H 0.9199 0.5419 0.4158 0.079 Uiso 1 1 calc R . .
C18 C 0.7109(11) 0.4502(8) 0.4085(7) 0.047(2) Uani 1 1 d . . .
H18 H 0.6894 0.4470 0.4875 0.056 Uiso 1 1 calc R . .
C19 C 0.6069(11) 0.3986(8) 0.3365(8) 0.051(3) Uani 1 1 d . . .
H19 H 0.5146 0.3598 0.3656 0.062 Uiso 1 1 calc R . .
C20 C 0.6409(10) 0.4048(7) 0.2197(7) 0.038(2) Uani 1 1 d . . .
C21 C 0.6147(10) 0.3765(7) 0.0332(7) 0.040(2) Uani 1 1 d . . .
C22 C 0.3981(10) 0.2657(8) -0.0576(9) 0.051(3) Uani 1 1 d . . .
H22 H 0.3526 0.2515 0.0157 0.061 Uiso 1 1 calc R . .
C23 C 0.3178(11) 0.2203(8) -0.1621(7) 0.045(2) Uani 1 1 d . . .
C24 C 0.3923(11) 0.2408(8) -0.2735(8) 0.055(3) Uani 1 1 d . . .
H24 H 0.3433 0.2106 -0.3374 0.066 Uiso 1 1 calc R . .
C25 C 0.5311(10) 0.3026(7) -0.2883(7) 0.042(2) Uani 1 1 d . . .
H25 H 0.5776 0.3127 -0.3614 0.050 Uiso 1 1 calc R . .
C26 C 0.6100(12) 0.3545(8) -0.1886(8) 0.053(3) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.718(8) . ?
S1 C1 1.745(8) . ?
O1 C13 1.253(9) . ?
O2 C10 1.215(9) . ?
N1 C1 1.318(9) . ?
N1 C7 1.354(9) . ?
C1 C8 1.431(10) . ?
C2 C3 1.423(11) . ?
C2 C7 1.428(10) . ?
C3 C4 1.350(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(10) . ?
C6 H6 0.9300 . ?
C8 C9 1.348(10) . ?
C8 C13 1.526(10) . ?
C9 C10 1.456(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.481(11) . ?
C11 C12 1.349(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.424(12) . ?
C12 H12 0.9300 . ?
S2 C15 1.717(11) . ?
S2 C21 1.741(8) . ?
O3 C26 1.234(9) . ?
O4 C23 1.240(9) . ?
N2 C21 1.281(10) . ?
N2 C20 1.419(9) . ?
C14 C22 1.375(10) . ?
C14 C26 1.471(12) . ?
C14 C21 1.505(11) . ?
C15 C20 1.412(11) . ?
C15 C16 1.440(11) . ?
C16 C17 1.315(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.399(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(11) . ?
C19 H19 0.9300 . ?
C22 C23 1.504(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.432(11) . ?
C24 C25 1.346(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.481(11) . ?
C25 H25 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
C2 S1 C1 88.8(4) . . ?
C1 N1 C7 111.4(7) . . ?
N1 C1 C8 119.0(7) . . ?
N1 C1 S1 115.5(6) . . ?
C8 C1 S1 125.5(6) . . ?
C3 C2 C7 121.0(8) . . ?
C3 C2 S1 129.0(7) . . ?
C7 C2 S1 110.0(6) . . ?
C4 C3 C2 119.2(8) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.9(7) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.7(8) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 122.5(8) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
N1 C7 C6 129.1(8) . . ?
N1 C7 C2 114.3(7) . . ?
C6 C7 C2 116.7(7) . . ?
C9 C8 C1 122.3(7) . . ?
C9 C8 C13 115.7(8) . . ?
C1 C8 C13 121.8(8) . . ?
C8 C9 C10 124.5(8) . . ?
C8 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
O2 C10 C9 120.5(8) . . ?
O2 C10 C11 121.8(8) . . ?
C9 C10 C11 117.6(8) . . ?
C12 C11 C10 119.2(8) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 122.7(8) . . ?
C11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
O1 C13 C12 121.5(8) . . ?
O1 C13 C8 118.6(8) . . ?
C12 C13 C8 119.8(8) . . ?
C15 S2 C21 87.1(4) . . ?
C21 N2 C20 110.3(7) . . ?
C22 C14 C26 120.8(9) . . ?
C22 C14 C21 117.3(8) . . ?
C26 C14 C21 121.7(8) . . ?
C20 C15 C16 116.6(9) . . ?
C20 C15 S2 112.7(7) . . ?
C16 C15 S2 130.7(7) . . ?
C17 C16 C15 120.1(9) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 122.1(9) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C17 120.5(9) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 118.8(8) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C15 122.0(8) . . ?
C19 C20 N2 126.6(8) . . ?
C15 C20 N2 111.4(8) . . ?
N2 C21 C14 119.9(7) . . ?
N2 C21 S2 118.4(7) . . ?
C14 C21 S2 121.6(6) . . ?
C14 C22 C23 118.6(9) . . ?
C14 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
O4 C23 C24 124.1(9) . . ?
O4 C23 C22 116.4(8) . . ?
C24 C23 C22 119.5(8) . . ?
C25 C24 C23 121.9(9) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C24 C25 C26 120.3(8) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
O3 C26 C14 124.1(9) . . ?
O3 C26 C25 117.3(9) . . ?
C14 C26 C25 118.6(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
C7 N1 C1 C8 178.2(7) . . . . ?
C7 N1 C1 S1 0.1(9) . . . . ?
C2 S1 C1 N1 -0.7(7) . . . . ?
C2 S1 C1 C8 -178.6(8) . . . . ?
C1 S1 C2 C3 178.2(8) . . . . ?
C1 S1 C2 C7 1.0(6) . . . . ?
C7 C2 C3 C4 -1.3(12) . . . . ?
S1 C2 C3 C4 -178.3(6) . . . . ?
C2 C3 C4 C5 1.2(12) . . . . ?
C3 C4 C5 C6 -2.0(12) . . . . ?
C4 C5 C6 C7 3.0(13) . . . . ?
C1 N1 C7 C6 179.7(8) . . . . ?
C1 N1 C7 C2 0.7(10) . . . . ?
C5 C6 C7 N1 177.9(8) . . . . ?
C5 C6 C7 C2 -3.1(12) . . . . ?
C3 C2 C7 N1 -178.6(7) . . . . ?
S1 C2 C7 N1 -1.1(9) . . . . ?
C3 C2 C7 C6 2.3(11) . . . . ?
S1 C2 C7 C6 179.7(6) . . . . ?
N1 C1 C8 C9 0.5(13) . . . . ?
S1 C1 C8 C9 178.3(6) . . . . ?
N1 C1 C8 C13 175.4(7) . . . . ?
S1 C1 C8 C13 -6.8(12) . . . . ?
C1 C8 C9 C10 -178.1(8) . . . . ?
C13 C8 C9 C10 6.7(12) . . . . ?
C8 C9 C10 O2 174.3(8) . . . . ?
C8 C9 C10 C11 -8.5(12) . . . . ?
O2 C10 C11 C12 -176.2(8) . . . . ?
C9 C10 C11 C12 6.6(12) . . . . ?
C10 C11 C12 C13 -3.8(13) . . . . ?
C11 C12 C13 O1 178.7(8) . . . . ?
C11 C12 C13 C8 2.1(13) . . . . ?
C9 C8 C13 O1 180.0(7) . . . . ?
C1 C8 C13 O1 4.8(12) . . . . ?
C9 C8 C13 C12 -3.3(11) . . . . ?
C1 C8 C13 C12 -178.5(7) . . . . ?
C21 S2 C15 C20 0.1(7) . . . . ?
C21 S2 C15 C16 -179.4(8) . . . . ?
C20 C15 C16 C17 1.7(12) . . . . ?
S2 C15 C16 C17 -178.8(7) . . . . ?
C15 C16 C17 C18 -1.4(13) . . . . ?
C16 C17 C18 C19 0.6(13) . . . . ?
C17 C18 C19 C20 -0.2(13) . . . . ?
C18 C19 C20 C15 0.6(13) . . . . ?
C18 C19 C20 N2 179.3(7) . . . . ?
C16 C15 C20 C19 -1.3(12) . . . . ?
S2 C15 C20 C19 179.1(6) . . . . ?
C16 C15 C20 N2 179.9(7) . . . . ?
S2 C15 C20 N2 0.3(9) . . . . ?
C21 N2 C20 C19 -179.4(8) . . . . ?
C21 N2 C20 C15 -0.6(10) . . . . ?
C20 N2 C21 C14 177.9(7) . . . . ?
C20 N2 C21 S2 0.8(9) . . . . ?
C22 C14 C21 N2 1.8(12) . . . . ?
C26 C14 C21 N2 177.9(8) . . . . ?
C22 C14 C21 S2 178.8(6) . . . . ?
C26 C14 C21 S2 -5.1(11) . . . . ?
C15 S2 C21 N2 -0.5(7) . . . . ?
C15 S2 C21 C14 -177.6(7) . . . . ?
C26 C14 C22 C23 1.9(12) . . . . ?
C21 C14 C22 C23 178.0(7) . . . . ?
C14 C22 C23 O4 -177.0(8) . . . . ?
C14 C22 C23 C24 1.5(12) . . . . ?
O4 C23 C24 C25 176.7(8) . . . . ?
C22 C23 C24 C25 -1.7(13) . . . . ?
C23 C24 C25 C26 -1.5(13) . . . . ?
C22 C14 C26 O3 177.4(8) . . . . ?
C21 C14 C26 O3 1.5(13) . . . . ?
C22 C14 C26 C25 -4.9(12) . . . . ?
C21 C14 C26 C25 179.1(7) . . . . ?
C24 C25 C26 O3 -177.4(8) . . . . ?
C24 C25 C26 C14 4.7(12) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2plm0y
_database_code_depnum_ccdc_archive 'CCDC 2490540'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2025-09-23 deposited with the CCDC.	2026-04-23 downloaded from the CCDC.
;
_audit_creation_date             2023-08-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N O2 S, C12 H4 N4'
_chemical_formula_sum            'C25 H13 N5 O2 S'
_chemical_formula_weight         447.46
_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 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.1304(10)
_cell_length_b                   8.0473(11)
_cell_length_c                   8.9775(13)
_cell_angle_alpha                81.093(6)
_cell_angle_beta                 89.834(6)
_cell_angle_gamma                87.729(6)
_cell_volume                     508.52(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    250
_cell_measurement_theta_max      68.12
_cell_measurement_theta_min      4.985
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.482
_exptl_absorpt_coefficient_mu    1.711
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5707
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '[ABSCOR(Rigaku, 2010)]'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             230
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.1545
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5769
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.198
_diffrn_reflns_theta_min         4.986
_diffrn_ambient_temperature      250
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.675
_reflns_Friedel_fraction_max     0.671
_reflns_number_gt                1317
_reflns_number_total             3083
_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       'RAPID AUTO (Rigaku, 2011)'
_computing_data_collection       'RAPID AUTO (Rigaku, 2011)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 
;
 Flack x determined using 324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1878
_refine_ls_R_factor_gt           0.1108
_refine_ls_restrained_S_all      0.985
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2772
_refine_ls_wR_factor_ref         0.3609
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C00A(H00A), C00B(H00B), C00H(H00H), C00J(H00J), C00N(H00N),
 C00O(H00O), C00P(H00P), C00T(H00T), C00U(H00U), C00W(H00W)
2.b Idealised tetrahedral OH refined as rotating group:
 O002(H002), O004(H004)
;
_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
S001 S 0.2560(8) 0.0466(6) 1.2412(5) 0.0748(15) Uani 1 1 d . . . . .
O002 O 0.277(2) -0.0717(16) 0.7548(13) 0.078(4) Uani 1 1 d . . . . .
H002 H 0.2796 -0.1375 0.8343 0.117 Uiso 1 1 calc R U . . .
N003 N 0.227(2) -0.1462(17) 1.0403(15) 0.059(4) Uani 1 1 d . . . . .
O004 O 0.450(2) 0.5635(14) 0.8523(15) 0.088(4) Uani 1 1 d . . . . .
H004 H 0.5524 0.5911 0.8181 0.132 Uiso 1 1 calc R U . . .
C005 C 0.787(3) 1.107(2) 0.0809(18) 0.064(5) Uani 1 1 d . . . . .
H005 H 0.8050 1.2167 0.0962 0.077 Uiso 1 1 calc R U . . .
C006 C 0.849(3) 1.182(2) -0.1909(17) 0.059(5) Uani 1 1 d . . . . .
C007 C 0.327(3) 0.129(2) 0.9268(18) 0.067(5) Uani 1 1 d . . . . .
C008 C 0.708(3) 0.829(2) 0.1750(18) 0.063(5) Uani 1 1 d . . . . .
C009 C 0.185(3) -0.160(2) 1.2996(19) 0.063(5) Uani 1 1 d . . . . .
C00A C 0.744(3) 1.000(2) 0.196(2) 0.071(6) Uani 1 1 d . . . . .
H00A H 0.7365 1.0310 0.2913 0.085 Uiso 1 1 calc R U . . .
C00B C 0.370(3) 0.291(2) 0.946(2) 0.073(5) Uani 1 1 d . . . . .
H00B H 0.3695 0.3236 1.0414 0.088 Uiso 1 1 calc R U . . .
N00C N 0.922(3) 1.491(2) -0.1605(18) 0.085(5) Uani 1 1 d . . . . .
C00D C 0.414(3) 0.399(2) 0.8232(19) 0.067(5) Uani 1 1 d . . . . .
N00E N 0.586(3) 0.404(2) 0.2683(18) 0.087(5) Uani 1 1 d . . . . .
N00F N 0.620(3) 0.763(2) 0.5658(18) 0.088(6) Uani 1 1 d . . . . .
C00G C 0.640(3) 0.746(2) 0.446(2) 0.071(5) Uani 1 1 d . . . . .
C00H C 0.125(3) -0.410(2) 1.197(2) 0.068(5) Uani 1 1 d . . . . .
H00H H 0.1193 -0.4674 1.1146 0.082 Uiso 1 1 calc R U . . .
C00I C 0.892(3) 1.353(2) -0.1715(19) 0.071(6) Uani 1 1 d . . . . .
C00J C 0.146(3) -0.233(2) 1.442(2) 0.076(6) Uani 1 1 d . . . . .
H00J H 0.1529 -0.1747 1.5239 0.091 Uiso 1 1 calc R U . . .
C00K C 0.328(3) 0.084(2) 0.7815(17) 0.066(6) Uani 1 1 d . . . . .
N00L N 0.891(3) 1.127(2) -0.4640(19) 0.095(6) Uani 1 1 d . . . . .
C00M C 0.811(3) 1.069(2) -0.0737(18) 0.062(5) Uani 1 1 d . . . . .
C00N C 0.093(3) -0.402(3) 1.460(2) 0.085(6) Uani 1 1 d . . . . .
H00N H 0.0642 -0.4562 1.5560 0.102 Uiso 1 1 calc R U . . .
C00O C 0.770(3) 0.899(2) -0.095(2) 0.069(5) Uani 1 1 d . . . . .
H00O H 0.7794 0.8674 -0.1908 0.083 Uiso 1 1 calc R U . . .
C00P C 0.428(3) 0.358(2) 0.680(2) 0.088(7) Uani 1 1 d . . . . .
H00P H 0.4670 0.4358 0.5989 0.106 Uiso 1 1 calc R U . . .
C00Q C 0.277(3) 0.002(2) 1.056(2) 0.071(5) Uani 1 1 d . . . . .
C00R C 0.869(3) 1.150(2) -0.340(2) 0.078(6) Uani 1 1 d . . . . .
C00S C 0.616(3) 0.539(2) 0.2793(18) 0.065(5) Uani 1 1 d . . . . .
C00T C 0.383(3) 0.197(2) 0.660(2) 0.071(5) Uani 1 1 d . . . . .
H00T H 0.3885 0.1661 0.5645 0.086 Uiso 1 1 calc R U . . .
C00U C 0.718(3) 0.784(2) 0.0252(17) 0.070(6) Uani 1 1 d . . . . .
H00U H 0.6880 0.6766 0.0107 0.084 Uiso 1 1 calc R U . . .
C00V C 0.176(3) -0.242(2) 1.178(2) 0.062(5) Uani 1 1 d . . . . .
C00W C 0.083(3) -0.488(2) 1.339(2) 0.069(5) Uani 1 1 d . . . . .
H00W H 0.0485 -0.5994 1.3546 0.083 Uiso 1 1 calc R U . . .
C00X C 0.655(3) 0.711(2) 0.2927(19) 0.068(5) Uani 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
S001 C009 1.759(18) . ?
S001 C00Q 1.759(19) . ?
O002 H002 0.8200 . ?
O002 C00K 1.377(18) . ?
N003 C00Q 1.29(2) . ?
N003 C00V 1.41(2) . ?
O004 H004 0.8200 . ?
O004 C00D 1.42(2) . ?
C005 H005 0.9300 . ?
C005 C00A 1.28(2) . ?
C005 C00M 1.47(2) . ?
C006 C00I 1.46(2) . ?
C006 C00M 1.32(2) . ?
C006 C00R 1.41(2) . ?
C007 C00B 1.39(2) . ?
C007 C00K 1.41(2) . ?
C007 C00Q 1.47(2) . ?
C008 C00A 1.45(2) . ?
C008 C00U 1.45(2) . ?
C008 C00X 1.37(2) . ?
C009 C00J 1.36(2) . ?
C009 C00V 1.36(2) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00B C00D 1.34(2) . ?
N00C C00I 1.16(2) . ?
C00D C00P 1.38(2) . ?
N00E C00S 1.14(2) . ?
N00F C00G 1.12(2) . ?
C00G C00X 1.45(2) . ?
C00H H00H 0.9300 . ?
C00H C00V 1.40(2) . ?
C00H C00W 1.37(2) . ?
C00J H00J 0.9300 . ?
C00J C00N 1.41(3) . ?
C00K C00T 1.37(2) . ?
N00L C00R 1.16(2) . ?
C00M C00O 1.45(2) . ?
C00N H00N 0.9300 . ?
C00N C00W 1.38(3) . ?
C00O H00O 0.9300 . ?
C00O C00U 1.37(2) . ?
C00P H00P 0.9300 . ?
C00P C00T 1.38(2) . ?
C00S C00X 1.45(2) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00W H00W 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
C00Q S001 C009 89.2(9) . . ?
C00K O002 H002 109.5 . . ?
C00Q N003 C00V 112.5(14) . . ?
C00D O004 H004 109.5 . . ?
C00A C005 H005 117.5 . . ?
C00A C005 C00M 125.0(16) . . ?
C00M C005 H005 117.5 . . ?
C00M C006 C00I 120.6(15) . . ?
C00M C006 C00R 125.4(17) . . ?
C00R C006 C00I 113.8(15) . . ?
C00B C007 C00K 119.8(15) . . ?
C00B C007 C00Q 121.2(15) . . ?
C00K C007 C00Q 118.9(15) . . ?
C00U C008 C00A 119.4(15) . . ?
C00X C008 C00A 121.3(15) . . ?
C00X C008 C00U 119.2(16) . . ?
C00J C009 S001 127.0(14) . . ?
C00J C009 C00V 123.3(17) . . ?
C00V C009 S001 109.6(13) . . ?
C005 C00A C008 118.9(16) . . ?
C005 C00A H00A 120.6 . . ?
C008 C00A H00A 120.6 . . ?
C007 C00B H00B 121.2 . . ?
C00D C00B C007 117.6(18) . . ?
C00D C00B H00B 121.2 . . ?
C00B C00D O004 114.0(17) . . ?
C00B C00D C00P 124.6(18) . . ?
C00P C00D O004 121.4(15) . . ?
N00F C00G C00X 175(2) . . ?
C00V C00H H00H 120.9 . . ?
C00W C00H H00H 120.9 . . ?
C00W C00H C00V 118.3(17) . . ?
N00C C00I C006 178(2) . . ?
C009 C00J H00J 121.9 . . ?
C009 C00J C00N 116.2(18) . . ?
C00N C00J H00J 121.9 . . ?
O002 C00K C007 122.2(14) . . ?
C00T C00K O002 117.6(15) . . ?
C00T C00K C007 120.2(16) . . ?
C006 C00M C005 124.0(16) . . ?
C006 C00M C00O 119.7(15) . . ?
C00O C00M C005 116.1(15) . . ?
C00J C00N H00N 119.1 . . ?
C00W C00N C00J 121.8(17) . . ?
C00W C00N H00N 119.1 . . ?
C00M C00O H00O 120.2 . . ?
C00U C00O C00M 119.6(16) . . ?
C00U C00O H00O 120.2 . . ?
C00D C00P H00P 121.2 . . ?
C00T C00P C00D 117.7(17) . . ?
C00T C00P H00P 121.2 . . ?
N003 C00Q S001 114.0(14) . . ?
N003 C00Q C007 122.5(16) . . ?
C007 C00Q S001 123.2(14) . . ?
N00L C00R C006 178(2) . . ?
N00E C00S C00X 179(2) . . ?
C00K C00T C00P 119.9(18) . . ?
C00K C00T H00T 120.0 . . ?
C00P C00T H00T 120.0 . . ?
C008 C00U H00U 119.5 . . ?
C00O C00U C008 120.9(16) . . ?
C00O C00U H00U 119.5 . . ?
C009 C00V N003 114.6(15) . . ?
C009 C00V C00H 120.1(17) . . ?
C00H C00V N003 125.2(15) . . ?
C00H C00W C00N 120.3(18) . . ?
C00H C00W H00W 119.9 . . ?
C00N C00W H00W 119.9 . . ?
C008 C00X C00G 122.8(16) . . ?
C008 C00X C00S 124.2(15) . . ?
C00G C00X C00S 113.0(15) . . ?

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
S001 C009 C00J C00N -179.6(15) . . . . ?
S001 C009 C00V N003 1(2) . . . . ?
S001 C009 C00V C00H 179.2(16) . . . . ?
O002 C00K C00T C00P 177.5(19) . . . . ?
O004 C00D C00P C00T -177.1(18) . . . . ?
C005 C00M C00O C00U -1(3) . . . . ?
C006 C00M C00O C00U -175.7(19) . . . . ?
C007 C00B C00D O004 177.8(17) . . . . ?
C007 C00B C00D C00P -4(3) . . . . ?
C007 C00K C00T C00P -3(3) . . . . ?
C009 S001 C00Q N003 3.0(17) . . . . ?
C009 S001 C00Q C007 176.9(19) . . . . ?
C009 C00J C00N C00W 0(3) . . . . ?
C00A C005 C00M C006 178(2) . . . . ?
C00A C005 C00M C00O 4(3) . . . . ?
C00A C008 C00U C00O 3(3) . . . . ?
C00A C008 C00X C00G -3(3) . . . . ?
C00A C008 C00X C00S 179.6(18) . . . . ?
C00B C007 C00K O002 -177(2) . . . . ?
C00B C007 C00K C00T 4(3) . . . . ?
C00B C007 C00Q S001 3(3) . . . . ?
C00B C007 C00Q N003 176.7(19) . . . . ?
C00B C00D C00P C00T 4(4) . . . . ?
C00D C00P C00T C00K -1(3) . . . . ?
C00I C006 C00M C005 7(3) . . . . ?
C00I C006 C00M C00O -179.4(18) . . . . ?
C00J C009 C00V N003 -178.5(19) . . . . ?
C00J C009 C00V C00H 0(3) . . . . ?
C00J C00N C00W C00H 0(3) . . . . ?
C00K C007 C00B C00D 0(3) . . . . ?
C00K C007 C00Q S001 -176.1(17) . . . . ?
C00K C007 C00Q N003 -3(3) . . . . ?
C00M C005 C00A C008 -2(3) . . . . ?
C00M C00O C00U C008 -2(3) . . . . ?
C00Q S001 C009 C00J 177(2) . . . . ?
C00Q S001 C009 C00V -2.3(15) . . . . ?
C00Q N003 C00V C009 1(2) . . . . ?
C00Q N003 C00V C00H -176.9(18) . . . . ?
C00Q C007 C00B C00D -180(2) . . . . ?
C00Q C007 C00K O002 3(3) . . . . ?
C00Q C007 C00K C00T -177.2(18) . . . . ?
C00R C006 C00M C005 -178.9(18) . . . . ?
C00R C006 C00M C00O -5(3) . . . . ?
C00U C008 C00A C005 -1(3) . . . . ?
C00U C008 C00X C00G -179.3(17) . . . . ?
C00U C008 C00X C00S 3(3) . . . . ?
C00V N003 C00Q S001 -3(2) . . . . ?
C00V N003 C00Q C007 -176.8(18) . . . . ?
C00V C009 C00J C00N 0(3) . . . . ?
C00V C00H C00W C00N 0(3) . . . . ?
C00W C00H C00V N003 178.4(16) . . . . ?
C00W C00H C00V C009 1(3) . . . . ?
C00X C008 C00A C005 -178(2) . . . . ?
C00X C008 C00U C00O 180(2) . . . . ?

_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_20230827_(5OH-HBT)(TCNQ)_350K
_database_code_depnum_ccdc_archive 'CCDC 2490988'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki AKUTAGAWA'
;Tohoku University
Japan
;
_audit_update_record             
;
2025-09-24 deposited with the CCDC.	2026-04-23 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H13 N5 O2 S'
_chemical_formula_moiety         'C25 H13 N5 O2 S'
_chemical_formula_weight         447.47
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_space_group_IT_number           1
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.2106(9)
_cell_length_b                   8.1058(10)
_cell_length_c                   17.975(2)
_cell_angle_alpha                81.082(6)
_cell_angle_beta                 89.865(6)
_cell_angle_gamma                88.183(6)
_cell_volume                     1037.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3258
_cell_measurement_theta_min      4.98
_cell_measurement_theta_max      67.80
_cell_measurement_temperature    350
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460.00
_exptl_absorpt_coefficient_mu    1.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_T_max  0.715

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      350
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12004
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_min         4.981
_diffrn_reflns_theta_full        68.250
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6265
_reflns_number_gt                2051
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2839
_refine_ls_wR_factor_gt          0.2109
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6265
_refine_ls_number_parameters     595
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1427P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2541 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.42(3)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.4054(5) 0.0422(5) 0.91028(19) 0.0768(10) Uani 1 1 d . . .
S2 S 0.4055(5) 0.0428(4) 0.41016(18) 0.0732(9) Uani 1 1 d . . .
O1 O 0.4333(12) -0.0761(11) 0.6670(4) 0.092(3) Uani 1 1 d . . .
H1 H 0.4024 -0.1335 0.7065 0.110 Uiso 1 1 calc R . .
O2 O 0.6026(11) 0.5578(10) 0.7155(5) 0.094(3) Uani 1 1 d . . .
H2A H 0.6312 0.6164 0.6760 0.113 Uiso 1 1 calc R . .
O3 O 0.4328(11) -0.0771(11) 0.1688(5) 0.088(3) Uani 1 1 d . . .
H3A H 0.3963 -0.1311 0.2082 0.106 Uiso 1 1 calc R . .
O4 O 0.6048(12) 0.5544(10) 0.2158(5) 0.093(3) Uani 1 1 d . . .
H4 H 0.6364 0.6099 0.1760 0.112 Uiso 1 1 calc R . .
N1 N 0.7704(17) -0.2422(15) 1.0748(7) 0.099(4) Uani 1 1 d . . .
N2 N 0.7377(19) -0.6009(15) 0.9235(7) 0.108(4) Uani 1 1 d . . .
N3 N 1.0354(16) 0.1250(16) 0.5580(6) 0.103(4) Uani 1 1 d . . .
N4 N 1.0731(18) 0.4826(16) 0.7111(7) 0.105(4) Uani 1 1 d . . .
N5 N 0.7711(18) -0.2417(16) 0.5736(7) 0.102(4) Uani 1 1 d . . .
N6 N 0.7340(17) -0.5988(14) 0.4236(7) 0.099(4) Uani 1 1 d . . .
N7 N 1.0377(16) 0.1217(15) 0.0596(6) 0.102(4) Uani 1 1 d . . .
N8 N 1.0694(16) 0.4783(17) 0.2114(7) 0.095(4) Uani 1 1 d . . .
N61 N 0.3746(15) -0.1539(13) 0.8108(6) 0.072(3) Uani 1 1 d . . .
N62 N 0.3750(14) -0.1502(13) 0.3104(5) 0.068(3) Uani 1 1 d . . .
C1 C 0.4170(15) -0.0023(16) 0.8177(6) 0.059(3) Uani 1 1 d . . .
C2 C 0.4723(16) 0.1240(17) 0.7526(7) 0.066(3) Uani 1 1 d . . .
C3 C 0.5155(15) 0.2876(14) 0.7619(6) 0.059(3) Uani 1 1 d . . .
H3 H 0.5101 0.3197 0.8094 0.071 Uiso 1 1 calc R . .
C4 C 0.5647(19) 0.3976(16) 0.7014(7) 0.073(4) Uani 1 1 d . . .
C5 C 0.5723(16) 0.3537(17) 0.6305(8) 0.077(4) Uani 1 1 d . . .
H5 H 0.6039 0.4322 0.5894 0.093 Uiso 1 1 calc R . .
C6 C 0.5320(17) 0.1891(16) 0.6202(8) 0.081(4) Uani 1 1 d . . .
H6 H 0.5424 0.1567 0.5729 0.097 Uiso 1 1 calc R . .
C7 C 0.4777(18) 0.0787(16) 0.6808(7) 0.070(4) Uani 1 1 d . . .
C8 C 0.3267(17) -0.2530(18) 0.8789(6) 0.071(4) Uani 1 1 d . . .
C9 C 0.2759(18) -0.4197(16) 0.8899(8) 0.085(4) Uani 1 1 d . . .
H9 H 0.2702 -0.4800 0.8500 0.101 Uiso 1 1 calc R . .
C10 C 0.2343(18) -0.4910(18) 0.9625(8) 0.094(5) Uani 1 1 d . . .
H10 H 0.2012 -0.6023 0.9720 0.112 Uiso 1 1 calc R . .
C11 C 0.2411(18) -0.3984(19) 1.0222(7) 0.085(4) Uani 1 1 d . . .
H11 H 0.2090 -0.4504 1.0701 0.102 Uiso 1 1 calc R . .
C12 C 0.2924(17) -0.2366(17) 1.0137(7) 0.078(4) Uani 1 1 d . . .
H12 H 0.2998 -0.1791 1.0545 0.094 Uiso 1 1 calc R . .
C13 C 0.3334(17) -0.1608(16) 0.9404(7) 0.065(3) Uani 1 1 d . . .
C14 C 0.4190(17) 0.0013(16) 0.3191(7) 0.064(3) Uani 1 1 d . . .
C15 C 0.4745(17) 0.1209(17) 0.2540(7) 0.066(4) Uani 1 1 d . . .
C16 C 0.5162(16) 0.2825(16) 0.2642(7) 0.070(4) Uani 1 1 d . . .
H16 H 0.5069 0.3139 0.3117 0.084 Uiso 1 1 calc R . .
C17 C 0.5707(17) 0.3940(18) 0.2044(8) 0.069(4) Uani 1 1 d . . .
C18 C 0.5709(18) 0.3551(16) 0.1318(8) 0.080(4) Uani 1 1 d . . .
H18 H 0.5994 0.4357 0.0911 0.096 Uiso 1 1 calc R . .
C19 C 0.5279(16) 0.1932(17) 0.1205(7) 0.082(4) Uani 1 1 d . . .
H19 H 0.5329 0.1631 0.0726 0.098 Uiso 1 1 calc R . .
C20 C 0.4784(18) 0.0812(15) 0.1813(7) 0.070(4) Uani 1 1 d . . .
C21 C 0.3280(16) -0.2415(15) 0.3809(7) 0.068(4) Uani 1 1 d . . .
C22 C 0.2738(17) -0.4109(17) 0.3865(7) 0.078(4) Uani 1 1 d . . .
H22 H 0.2645 -0.4651 0.3448 0.094 Uiso 1 1 calc R . .
C23 C 0.2355(17) -0.4897(17) 0.4603(9) 0.089(4) Uani 1 1 d . . .
H23 H 0.2071 -0.6021 0.4682 0.106 Uiso 1 1 calc R . .
C24 C 0.2390(18) -0.4038(18) 0.5217(8) 0.085(4) Uani 1 1 d . . .
H24 H 0.2070 -0.4585 0.5692 0.102 Uiso 1 1 calc R . .
C25 C 0.2891(17) -0.2395(19) 0.5135(7) 0.085(5) Uani 1 1 d . . .
H25 H 0.2942 -0.1834 0.5547 0.102 Uiso 1 1 calc R . .
C26 C 0.3307(18) -0.1615(16) 0.4431(8) 0.068(4) Uani 1 1 d . . .
C27 C 0.7900(18) -0.2611(17) 1.0118(7) 0.073(4) Uani 1 1 d . . .
C28 C 0.8028(17) -0.2949(16) 0.9365(7) 0.069(4) Uani 1 1 d . . .
C29 C 0.7700(19) -0.464(2) 0.9285(8) 0.082(4) Uani 1 1 d . . .
C30 C 0.8565(16) -0.1776(15) 0.8766(7) 0.061(3) Uani 1 1 d . . .
C31 C 0.8921(17) -0.0114(15) 0.8881(7) 0.067(4) Uani 1 1 d . . .
H31 H 0.8835 0.0152 0.9365 0.081 Uiso 1 1 calc R . .
C32 C 0.9383(16) 0.1097(16) 0.8303(6) 0.063(3) Uani 1 1 d . . .
H32 H 0.9591 0.2180 0.8387 0.076 Uiso 1 1 calc R . .
C33 C 0.9542(18) 0.0648(16) 0.7549(7) 0.066(3) Uani 1 1 d . . .
C34 C 0.9171(16) -0.1017(16) 0.7441(7) 0.075(4) Uani 1 1 d . . .
H34 H 0.9285 -0.1300 0.6960 0.090 Uiso 1 1 calc R . .
C35 C 0.8656(15) -0.2209(17) 0.8019(6) 0.067(4) Uani 1 1 d . . .
H35 H 0.8371 -0.3275 0.7933 0.081 Uiso 1 1 calc R . .
C36 C 1.0058(17) 0.1833(17) 0.6951(7) 0.071(4) Uani 1 1 d . . .
C37 C 1.0429(18) 0.3509(17) 0.7052(7) 0.068(4) Uani 1 1 d . . .
C38 C 1.0215(19) 0.1472(16) 0.6194(7) 0.077(4) Uani 1 1 d . . .
C39 C 0.8027(16) -0.2920(16) 0.4360(7) 0.066(4) Uani 1 1 d . . .
C40 C 0.7913(18) -0.2606(18) 0.5109(8) 0.077(4) Uani 1 1 d . . .
C41 C 0.770(2) -0.462(2) 0.4280(8) 0.086(4) Uani 1 1 d . . .
C42 C 0.8538(17) -0.1765(17) 0.3767(6) 0.065(4) Uani 1 1 d . . .
C43 C 0.8945(16) -0.0052(16) 0.3882(7) 0.064(4) Uani 1 1 d . . .
H43 H 0.8865 0.0236 0.4362 0.077 Uiso 1 1 calc R . .
C44 C 0.9430(16) 0.1098(17) 0.3298(6) 0.066(4) Uani 1 1 d . . .
H44 H 0.9689 0.2178 0.3371 0.079 Uiso 1 1 calc R . .
C45 C 0.9544(17) 0.0621(16) 0.2545(6) 0.061(3) Uani 1 1 d . . .
C46 C 0.9151(15) -0.1049(14) 0.2448(6) 0.065(3) Uani 1 1 d . . .
H46 H 0.9236 -0.1347 0.1969 0.079 Uiso 1 1 calc R . .
C47 C 0.8658(16) -0.2213(17) 0.3036(6) 0.073(4) Uani 1 1 d . . .
H47 H 0.8401 -0.3292 0.2960 0.088 Uiso 1 1 calc R . .
C48 C 1.0037(17) 0.1790(16) 0.1957(7) 0.068(4) Uani 1 1 d . . .
C49 C 1.040(2) 0.3452(18) 0.2043(8) 0.081(5) Uani 1 1 d . . .
C50 C 1.0199(18) 0.1487(16) 0.1197(8) 0.076(4) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C13 1.746(13) . ?
S1 C1 1.757(12) . ?
S2 C14 1.723(12) . ?
S2 C26 1.771(13) . ?
O1 C7 1.364(13) . ?
O1 H1 0.8200 . ?
O2 C4 1.396(13) . ?
O2 H2A 0.8200 . ?
O3 C20 1.385(13) . ?
O3 H3A 0.8200 . ?
O4 C17 1.377(14) . ?
O4 H4 0.8200 . ?
N1 C27 1.173(14) . ?
N2 C29 1.160(16) . ?
N3 C38 1.150(14) . ?
N4 C37 1.117(15) . ?
N5 C40 1.168(15) . ?
N6 C41 1.159(15) . ?
N7 C50 1.140(14) . ?
N8 C49 1.132(16) . ?
N61 C1 1.300(14) . ?
N61 C8 1.406(15) . ?
N62 C14 1.310(13) . ?
N62 C21 1.411(14) . ?
C1 C2 1.493(15) . ?
C2 C7 1.396(16) . ?
C2 C3 1.406(15) . ?
C3 C4 1.350(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(15) . ?
C5 C6 1.415(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.363(15) . ?
C6 H6 0.9300 . ?
C8 C9 1.396(16) . ?
C8 C13 1.428(16) . ?
C9 C10 1.379(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.400(14) . ?
C12 H12 0.9300 . ?
C14 C15 1.463(15) . ?
C15 C16 1.393(16) . ?
C15 C20 1.395(15) . ?
C16 C17 1.360(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(15) . ?
C18 C19 1.404(15) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(15) . ?
C19 H19 0.9300 . ?
C21 C26 1.378(17) . ?
C21 C22 1.428(15) . ?
C22 C23 1.410(17) . ?
C22 H22 0.9300 . ?
C23 C24 1.394(17) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(18) . ?
C24 H24 0.9300 . ?
C25 C26 1.360(15) . ?
C25 H25 0.9300 . ?
C27 C28 1.424(15) . ?
C28 C30 1.384(15) . ?
C28 C29 1.426(18) . ?
C30 C31 1.426(14) . ?
C30 C35 1.441(14) . ?
C31 C32 1.363(15) . ?
C31 H31 0.9300 . ?
C32 C33 1.461(14) . ?
C32 H32 0.9300 . ?
C33 C36 1.385(16) . ?
C33 C34 1.427(15) . ?
C34 C35 1.364(15) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.432(16) . ?
C36 C38 1.438(16) . ?
C39 C42 1.364(15) . ?
C39 C40 1.410(16) . ?
C39 C41 1.437(17) . ?
C42 C47 1.419(14) . ?
C42 C43 1.473(15) . ?
C43 C44 1.345(16) . ?
C43 H43 0.9300 . ?
C44 C45 1.465(14) . ?
C44 H44 0.9300 . ?
C45 C48 1.361(16) . ?
C45 C46 1.429(14) . ?
C46 C47 1.358(14) . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?
C48 C49 1.413(16) . ?
C48 C50 1.429(16) . ?

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
C13 S1 C1 89.1(6) . . ?
C14 S2 C26 91.4(6) . . ?
C7 O1 H1 109.5 . . ?
C4 O2 H2A 109.5 . . ?
C20 O3 H3A 109.5 . . ?
C17 O4 H4 109.5 . . ?
C1 N61 C8 114.0(11) . . ?
C14 N62 C21 109.4(11) . . ?
N61 C1 C2 122.9(11) . . ?
N61 C1 S1 114.6(9) . . ?
C2 C1 S1 122.5(10) . . ?
C7 C2 C3 119.6(12) . . ?
C7 C2 C1 118.9(12) . . ?
C3 C2 C1 121.5(12) . . ?
C4 C3 C2 119.5(12) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.4(13) . . ?
C3 C4 O2 115.7(13) . . ?
C5 C4 O2 122.9(12) . . ?
C4 C5 C6 120.0(12) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 118.8(13) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 O1 116.4(12) . . ?
C6 C7 C2 120.7(13) . . ?
O1 C7 C2 123.0(12) . . ?
C9 C8 N61 127.6(12) . . ?
C9 C8 C13 121.1(12) . . ?
N61 C8 C13 111.3(12) . . ?
C10 C9 C8 117.1(14) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C9 C10 C11 121.1(14) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 123.4(13) . . ?
C12 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C11 C12 C13 116.6(14) . . ?
C11 C12 H12 121.7 . . ?
C13 C12 H12 121.7 . . ?
C12 C13 C8 120.7(12) . . ?
C12 C13 S1 128.2(11) . . ?
C8 C13 S1 111.0(9) . . ?
N62 C14 C15 120.0(12) . . ?
N62 C14 S2 115.1(10) . . ?
C15 C14 S2 124.8(10) . . ?
C16 C15 C20 118.6(12) . . ?
C16 C15 C14 119.1(12) . . ?
C20 C15 C14 122.2(13) . . ?
C17 C16 C15 119.7(13) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 O4 118.3(13) . . ?
C16 C17 C18 121.4(13) . . ?
O4 C17 C18 119.9(13) . . ?
C17 C18 C19 119.5(13) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 118.4(13) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 O3 117.6(12) . . ?
C19 C20 C15 122.2(13) . . ?
O3 C20 C15 120.2(12) . . ?
C26 C21 N62 118.3(12) . . ?
C26 C21 C22 121.3(12) . . ?
N62 C21 C22 120.4(13) . . ?
C23 C22 C21 114.8(12) . . ?
C23 C22 H22 122.6 . . ?
C21 C22 H22 122.6 . . ?
C24 C23 C22 121.9(13) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C25 C24 C23 121.2(13) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C26 C25 C24 118.1(14) . . ?
C26 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
C25 C26 C21 122.6(13) . . ?
C25 C26 S2 131.6(12) . . ?
C21 C26 S2 105.7(10) . . ?
N1 C27 C28 175.2(15) . . ?
C30 C28 C27 123.1(13) . . ?
C30 C28 C29 122.3(12) . . ?
C27 C28 C29 114.4(12) . . ?
N2 C29 C28 177.6(17) . . ?
C28 C30 C31 120.0(12) . . ?
C28 C30 C35 120.0(12) . . ?
C31 C30 C35 120.0(12) . . ?
C32 C31 C30 122.0(12) . . ?
C32 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
C31 C32 C33 118.2(12) . . ?
C31 C32 H32 120.9 . . ?
C33 C32 H32 120.9 . . ?
C36 C33 C34 120.9(13) . . ?
C36 C33 C32 119.9(13) . . ?
C34 C33 C32 119.2(11) . . ?
C35 C34 C33 122.2(12) . . ?
C35 C34 H34 118.9 . . ?
C33 C34 H34 118.9 . . ?
C34 C35 C30 118.3(13) . . ?
C34 C35 H35 120.8 . . ?
C30 C35 H35 120.8 . . ?
C33 C36 C37 121.4(12) . . ?
C33 C36 C38 122.4(13) . . ?
C37 C36 C38 116.2(11) . . ?
N4 C37 C36 178.1(14) . . ?
N3 C38 C36 177.2(15) . . ?
C42 C39 C40 123.9(13) . . ?
C42 C39 C41 122.1(12) . . ?
C40 C39 C41 113.8(12) . . ?
N5 C40 C39 175.2(16) . . ?
N6 C41 C39 176.3(18) . . ?
C39 C42 C47 119.7(13) . . ?
C39 C42 C43 120.3(11) . . ?
C47 C42 C43 120.0(12) . . ?
C44 C43 C42 120.6(11) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 118.9(12) . . ?
C43 C44 H44 120.5 . . ?
C45 C44 H44 120.5 . . ?
C48 C45 C46 121.8(12) . . ?
C48 C45 C44 118.6(13) . . ?
C46 C45 C44 119.6(11) . . ?
C47 C46 C45 121.7(11) . . ?
C47 C46 H46 119.2 . . ?
C45 C46 H46 119.2 . . ?
C46 C47 C42 119.3(13) . . ?
C46 C47 H47 120.4 . . ?
C42 C47 H47 120.4 . . ?
C45 C48 C49 122.4(12) . . ?
C45 C48 C50 124.2(13) . . ?
C49 C48 C50 113.4(11) . . ?
N8 C49 C48 180(2) . . ?
N7 C50 C48 177.9(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N61 C1 C2 179.9(10) . . . . ?
C8 N61 C1 S1 0.3(14) . . . . ?
C13 S1 C1 N61 -1.1(10) . . . . ?
C13 S1 C1 C2 179.3(10) . . . . ?
N61 C1 C2 C7 0.5(18) . . . . ?
S1 C1 C2 C7 -179.9(9) . . . . ?
N61 C1 C2 C3 179.3(11) . . . . ?
S1 C1 C2 C3 -1.1(16) . . . . ?
C7 C2 C3 C4 -1.2(19) . . . . ?
C1 C2 C3 C4 -180.0(12) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C2 C3 C4 O2 179.1(11) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
O2 C4 C5 C6 -179.9(12) . . . . ?
C4 C5 C6 C7 3.0(19) . . . . ?
C5 C6 C7 O1 177.4(11) . . . . ?
C5 C6 C7 C2 -4(2) . . . . ?
C3 C2 C7 C6 3(2) . . . . ?
C1 C2 C7 C6 -178.3(11) . . . . ?
C3 C2 C7 O1 -178.4(11) . . . . ?
C1 C2 C7 O1 0.5(19) . . . . ?
C1 N61 C8 C9 -179.7(12) . . . . ?
C1 N61 C8 C13 0.9(16) . . . . ?
N61 C8 C9 C10 -179.9(13) . . . . ?
C13 C8 C9 C10 -0.5(19) . . . . ?
C8 C9 C10 C11 1(2) . . . . ?
C9 C10 C11 C12 -2(2) . . . . ?
C10 C11 C12 C13 2(2) . . . . ?
C11 C12 C13 C8 -2.0(19) . . . . ?
C11 C12 C13 S1 -179.2(11) . . . . ?
C9 C8 C13 C12 1.2(19) . . . . ?
N61 C8 C13 C12 -179.3(11) . . . . ?
C9 C8 C13 S1 178.9(10) . . . . ?
N61 C8 C13 S1 -1.7(14) . . . . ?
C1 S1 C13 C12 179.0(12) . . . . ?
C1 S1 C13 C8 1.5(10) . . . . ?
C21 N62 C14 C15 179.6(11) . . . . ?
C21 N62 C14 S2 -0.4(13) . . . . ?
C26 S2 C14 N62 -0.5(11) . . . . ?
C26 S2 C14 C15 179.4(11) . . . . ?
N62 C14 C15 C16 178.4(11) . . . . ?
S2 C14 C15 C16 -1.6(18) . . . . ?
N62 C14 C15 C20 2(2) . . . . ?
S2 C14 C15 C20 -178.4(10) . . . . ?
C20 C15 C16 C17 -4.1(19) . . . . ?
C14 C15 C16 C17 179.0(12) . . . . ?
C15 C16 C17 O4 177.8(11) . . . . ?
C15 C16 C17 C18 5(2) . . . . ?
C16 C17 C18 C19 -5(2) . . . . ?
O4 C17 C18 C19 -177.2(11) . . . . ?
C17 C18 C19 C20 3.1(19) . . . . ?
C18 C19 C20 O3 178.7(11) . . . . ?
C18 C19 C20 C15 -2(2) . . . . ?
C16 C15 C20 C19 2(2) . . . . ?
C14 C15 C20 C19 179.2(12) . . . . ?
C16 C15 C20 O3 -178.3(11) . . . . ?
C14 C15 C20 O3 -1(2) . . . . ?
C14 N62 C21 C26 1.6(16) . . . . ?
C14 N62 C21 C22 179.7(11) . . . . ?
C26 C21 C22 C23 -3.6(18) . . . . ?
N62 C21 C22 C23 178.3(11) . . . . ?
C21 C22 C23 C24 4.0(18) . . . . ?
C22 C23 C24 C25 -3(2) . . . . ?
C23 C24 C25 C26 2(2) . . . . ?
C24 C25 C26 C21 -1(2) . . . . ?
C24 C25 C26 S2 -178.1(11) . . . . ?
N62 C21 C26 C25 -179.5(11) . . . . ?
C22 C21 C26 C25 2(2) . . . . ?
N62 C21 C26 S2 -1.9(15) . . . . ?
C22 C21 C26 S2 180.0(10) . . . . ?
C14 S2 C26 C25 178.5(13) . . . . ?
C14 S2 C26 C21 1.3(10) . . . . ?
N1 C27 C28 C30 155(19) . . . . ?
N1 C27 C28 C29 -30(20) . . . . ?
C30 C28 C29 N2 -134(41) . . . . ?
C27 C28 C29 N2 51(42) . . . . ?
C27 C28 C30 C31 -4(2) . . . . ?
C29 C28 C30 C31 -178.4(11) . . . . ?
C27 C28 C30 C35 -179.8(11) . . . . ?
C29 C28 C30 C35 5(2) . . . . ?
C28 C30 C31 C32 -177.4(13) . . . . ?
C35 C30 C31 C32 -1.1(19) . . . . ?
C30 C31 C32 C33 -1.0(19) . . . . ?
C31 C32 C33 C36 -178.3(13) . . . . ?
C31 C32 C33 C34 1.4(18) . . . . ?
C36 C33 C34 C35 -179.8(13) . . . . ?
C32 C33 C34 C35 0.5(19) . . . . ?
C33 C34 C35 C30 -2.7(18) . . . . ?
C28 C30 C35 C34 179.3(12) . . . . ?
C31 C30 C35 C34 3.0(18) . . . . ?
C34 C33 C36 C37 179.9(12) . . . . ?
C32 C33 C36 C37 -1(2) . . . . ?
C34 C33 C36 C38 1(2) . . . . ?
C32 C33 C36 C38 -179.2(11) . . . . ?
C33 C36 C37 N4 178(100) . . . . ?
C38 C36 C37 N4 -3(50) . . . . ?
C33 C36 C38 N3 174(34) . . . . ?
C37 C36 C38 N3 -5(35) . . . . ?
C42 C39 C40 N5 144(19) . . . . ?
C41 C39 C40 N5 -41(20) . . . . ?
C42 C39 C41 N6 -131(25) . . . . ?
C40 C39 C41 N6 54(26) . . . . ?
C40 C39 C42 C47 178.4(11) . . . . ?
C41 C39 C42 C47 3(2) . . . . ?
C40 C39 C42 C43 -2(2) . . . . ?
C41 C39 C42 C43 -177.3(11) . . . . ?
C39 C42 C43 C44 -179.3(12) . . . . ?
C47 C42 C43 C44 0.0(18) . . . . ?
C42 C43 C44 C45 0.2(18) . . . . ?
C43 C44 C45 C48 -180.0(12) . . . . ?
C43 C44 C45 C46 -0.4(17) . . . . ?
C48 C45 C46 C47 -179.9(13) . . . . ?
C44 C45 C46 C47 0.5(18) . . . . ?
C45 C46 C47 C42 -0.4(19) . . . . ?
C39 C42 C47 C46 179.4(12) . . . . ?
C43 C42 C47 C46 0.1(19) . . . . ?
C46 C45 C48 C49 179.0(12) . . . . ?
C44 C45 C48 C49 -1(2) . . . . ?
C46 C45 C48 C50 0(2) . . . . ?
C44 C45 C48 C50 180.0(11) . . . . ?
C45 C48 C49 N8 48(100) . . . . ?
C50 C48 C49 N8 -134(100) . . . . ?
C45 C48 C50 N7 -74(43) . . . . ?
C49 C48 C50 N7 108(42) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N61 . . . 2.600(13) 0.820 1.867 148.1 no
O3 H3A N62 . . . 2.559(12) 0.820 1.827 147.9 no
O4 H4 N1 . . 1_564 3.064(14) 0.820 2.252 170.6 no
####################################################################### 
# 
# 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_shelx_trans
_audit_block_doi                 10.5517/ccdc.csd.cc2pllyv
_database_code_depnum_ccdc_archive 'CCDC 2490538'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2025-09-23 deposited with the CCDC.	2026-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N O2 S'
_chemical_formula_sum            'C13 H9 N O2 S'
_chemical_formula_weight         243.27
_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 0.0181 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                   4.6624(3)
_cell_length_b                   19.8629(9)
_cell_length_c                   23.2360(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2151.86(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1712
_cell_measurement_temperature    100
_cell_measurement_theta_max      3.815
_cell_measurement_theta_min      68.255
_shelx_estimated_absorpt_T_max   0.782
_shelx_estimated_absorpt_T_min   0.625
_exptl_absorpt_coefficient_mu    2.575
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7238
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '[ABSCOR(Rigaku, 2010)]'
_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    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.1458
_diffrn_reflns_Laue_measured_fraction_full 0.872
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4562
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.161
_diffrn_reflns_theta_min         3.805
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                884
_reflns_number_total             1712
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1621
_refine_ls_R_factor_gt           0.0845
_refine_ls_restrained_S_all      1.018
_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)+(0.0944P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00F(H00F), C00G(H00G),
 C00H(H00H)
2.b Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003)
;
_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
S001 S 0.3411(4) 0.39843(9) 0.69365(6) 0.0460(6) Uani 1 1 d . . . . .
O002 O 0.9872(9) 0.1825(3) 0.72014(16) 0.0479(14) Uani 1 1 d . . . . .
H002 H 0.842681 0.182181 0.740239 0.072 Uiso 1 1 calc R U . . .
O003 O 0.8585(10) 0.3473(2) 0.52971(17) 0.0546(15) Uani 1 1 d . . . . .
H003 H 0.718508 0.372087 0.532766 0.082 Uiso 1 1 calc R U . . .
N004 N 0.4789(11) 0.4182(3) 0.5871(2) 0.0429(17) Uani 1 1 d . . . . .
C005 C 0.9461(15) 0.2255(4) 0.6736(2) 0.0394(19) Uani 1 1 d . . . . .
C006 C 0.7232(15) 0.3220(4) 0.6282(2) 0.0408(19) Uani 1 1 d . . . . .
C007 C 0.2784(15) 0.4672(4) 0.6003(2) 0.0404(19) Uani 1 1 d . . . . .
C008 C 0.1741(15) 0.5173(4) 0.5634(3) 0.043(2) Uani 1 1 d . . . . .
H008 H 0.242915 0.521062 0.525986 0.052 Uiso 1 1 calc R U . . .
C009 C 0.7648(14) 0.2801(4) 0.6757(2) 0.0383(19) Uani 1 1 d . . . . .
H009 H 0.667224 0.289381 0.709674 0.046 Uiso 1 1 calc R U . . .
C00A C 0.1786(15) 0.4639(3) 0.6580(2) 0.0371(18) Uani 1 1 d . . . . .
C00B C -0.0250(15) 0.5101(4) 0.6783(2) 0.049(2) Uani 1 1 d . . . . .
H00B H -0.089473 0.508616 0.716171 0.058 Uiso 1 1 calc R U . . .
C00C C 1.1027(15) 0.2135(4) 0.6236(2) 0.043(2) Uani 1 1 d . . . . .
H00C H 1.229796 0.177461 0.621887 0.052 Uiso 1 1 calc R U . . .
C00D C 0.5293(15) 0.3792(4) 0.6305(2) 0.0353(19) Uani 1 1 d . . . . .
C00E C 0.8829(14) 0.3088(4) 0.5777(3) 0.043(2) Uani 1 1 d . . . . .
C00F C -0.1266(15) 0.5579(4) 0.6404(3) 0.044(2) Uani 1 1 d . . . . .
H00F H -0.261915 0.589028 0.652958 0.053 Uiso 1 1 calc R U . . .
C00G C 1.0694(15) 0.2550(4) 0.5767(2) 0.052(2) Uani 1 1 d . . . . .
H00G H 1.175084 0.246504 0.543535 0.062 Uiso 1 1 calc R U . . .
C00H C -0.0303(15) 0.5606(4) 0.5835(3) 0.047(2) Uani 1 1 d . . . . .
H00H H -0.107414 0.592521 0.558644 0.057 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
S001 C00A 1.718(7) . ?
S001 C00D 1.752(6) . ?
O002 H002 0.8200 . ?
O002 C005 1.392(7) . ?
O003 H003 0.8200 . ?
O003 C00E 1.358(7) . ?
N004 C007 1.385(8) . ?
N004 C00D 1.293(7) . ?
C005 C009 1.377(8) . ?
C005 C00C 1.393(8) . ?
C006 C009 1.395(8) . ?
C006 C00D 1.453(9) . ?
C006 C00E 1.414(8) . ?
C007 C008 1.401(8) . ?
C007 C00A 1.421(8) . ?
C008 H008 0.9300 . ?
C008 C00H 1.365(8) . ?
C009 H009 0.9300 . ?
C00A C00B 1.402(9) . ?
C00B H00B 0.9300 . ?
C00B C00F 1.379(8) . ?
C00C H00C 0.9300 . ?
C00C C00G 1.374(8) . ?
C00E C00G 1.379(9) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.398(8) . ?
C00G H00G 0.9300 . ?
C00H H00H 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
C00A S001 C00D 89.0(3) . . ?
C005 O002 H002 109.5 . . ?
C00E O003 H003 109.5 . . ?
C00D N004 C007 111.7(6) . . ?
O002 C005 C00C 118.1(7) . . ?
C009 C005 O002 122.8(6) . . ?
C009 C005 C00C 119.1(6) . . ?
C009 C006 C00D 121.6(6) . . ?
C009 C006 C00E 118.2(7) . . ?
C00E C006 C00D 120.2(6) . . ?
N004 C007 C008 126.7(6) . . ?
N004 C007 C00A 113.5(6) . . ?
C008 C007 C00A 119.8(7) . . ?
C007 C008 H008 120.6 . . ?
C00H C008 C007 118.7(6) . . ?
C00H C008 H008 120.6 . . ?
C005 C009 C006 121.9(6) . . ?
C005 C009 H009 119.1 . . ?
C006 C009 H009 119.1 . . ?
C007 C00A S001 110.2(5) . . ?
C00B C00A S001 129.2(5) . . ?
C00B C00A C007 120.6(6) . . ?
C00A C00B H00B 121.0 . . ?
C00F C00B C00A 117.9(6) . . ?
C00F C00B H00B 121.0 . . ?
C005 C00C H00C 120.0 . . ?
C00G C00C C005 120.0(7) . . ?
C00G C00C H00C 120.0 . . ?
N004 C00D S001 115.6(6) . . ?
N004 C00D C006 123.6(6) . . ?
C006 C00D S001 120.8(5) . . ?
O003 C00E C006 122.2(7) . . ?
O003 C00E C00G 118.4(6) . . ?
C00G C00E C006 119.4(7) . . ?
C00B C00F H00F 119.3 . . ?
C00B C00F C00H 121.3(7) . . ?
C00H C00F H00F 119.3 . . ?
C00C C00G C00E 121.5(6) . . ?
C00C C00G H00G 119.2 . . ?
C00E C00G H00G 119.2 . . ?
C008 C00H C00F 121.6(7) . . ?
C008 C00H H00H 119.2 . . ?
C00F C00H H00H 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
S001 C00A C00B C00F -179.0(5) . . . . ?
O002 C005 C009 C006 -179.0(6) . . . . ?
O002 C005 C00C C00G -179.7(6) . . . . ?
O003 C00E C00G C00C -179.4(6) . . . . ?
N004 C007 C008 C00H 178.2(7) . . . . ?
N004 C007 C00A S001 -0.3(7) . . . . ?
N004 C007 C00A C00B 179.9(6) . . . . ?
C005 C00C C00G C00E 0.0(11) . . . . ?
C006 C00E C00G C00C 0.4(11) . . . . ?
C007 N004 C00D S001 -0.9(8) . . . . ?
C007 N004 C00D C006 177.8(6) . . . . ?
C007 C008 C00H C00F 3.2(11) . . . . ?
C007 C00A C00B C00F 0.8(10) . . . . ?
C008 C007 C00A S001 -179.8(5) . . . . ?
C008 C007 C00A C00B 0.4(10) . . . . ?
C009 C005 C00C C00G -1.7(10) . . . . ?
C009 C006 C00D S001 0.6(10) . . . . ?
C009 C006 C00D N004 -178.1(6) . . . . ?
C009 C006 C00E O003 -179.3(6) . . . . ?
C009 C006 C00E C00G 1.0(10) . . . . ?
C00A S001 C00D N004 0.7(6) . . . . ?
C00A S001 C00D C006 -178.1(6) . . . . ?
C00A C007 C008 C00H -2.4(10) . . . . ?
C00A C00B C00F C00H -0.1(11) . . . . ?
C00B C00F C00H C008 -2.0(11) . . . . ?
C00C C005 C009 C006 3.1(10) . . . . ?
C00D S001 C00A C007 -0.2(5) . . . . ?
C00D S001 C00A C00B 179.6(7) . . . . ?
C00D N004 C007 C008 -179.8(7) . . . . ?
C00D N004 C007 C00A 0.8(8) . . . . ?
C00D C006 C009 C005 179.4(6) . . . . ?
C00D C006 C00E O003 -1.4(10) . . . . ?
C00D C006 C00E C00G 178.9(7) . . . . ?
C00E C006 C009 C005 -2.7(10) . . . . ?
C00E C006 C00D S001 -177.3(5) . . . . ?
C00E C006 C00D N004 4.0(11) . . . . ?

_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_shelx_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2plm1z
_database_code_depnum_ccdc_archive 'CCDC 2490541'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2025-09-23 deposited with the CCDC.	2026-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-07-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N O2 S, C6 H4 O2'
_chemical_formula_sum            'C19 H13 N O4 S'
_chemical_formula_weight         351.36
_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 0.0181 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7414(2)
_cell_length_b                   7.1020(3)
_cell_length_c                   17.5255(6)
_cell_angle_alpha                83.108(6)
_cell_angle_beta                 79.950(6)
_cell_angle_gamma                65.888(5)
_cell_volume                     753.00(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6628
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.245
_cell_measurement_theta_min      5.135
_shelx_estimated_absorpt_T_max   0.814
_shelx_estimated_absorpt_T_min   0.414
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6354
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '[ABSCOR(Rigaku, 2010)]'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_unetI/netI     0.1082
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8713
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         5.134
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1830
_reflns_number_total             2687
_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       'RAPID AUTO (Rigaku, 2011)'
_computing_data_collection       'RAPID AUTO (Rigaku, 2011)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.071
_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)+(0.1188P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.2215
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C016(H016), C018(H018), C019(H019), C023(H023), C026(H026)
2.b Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005)
;
_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 0.25541(16) 0.40214(16) 0.36553(5) 0.0317(4) Uani 1 1 d . . . . .
O002 O 0.3513(5) -0.0161(5) 0.25096(16) 0.0368(8) Uani 1 1 d . . . . .
O003 O -0.2589(5) 0.1437(4) 0.06888(15) 0.0324(7) Uani 1 1 d . . . . .
O004 O 0.2124(5) 0.6573(5) 0.07189(16) 0.0357(8) Uani 1 1 d . . . . .
H004 H 0.2368 0.7171 0.0292 0.054 Uiso 1 1 calc R U . . .
O005 O 0.8824(5) 0.4775(5) 0.24455(16) 0.0352(7) Uani 1 1 d . . . . .
H005 H 0.8560 0.4252 0.2887 0.053 Uiso 1 1 calc R U . . .
C006 C 0.2114(7) 0.0182(7) 0.2089(2) 0.0316(10) Uani 1 1 d . . . . .
C007 C 0.5261(6) 0.4812(6) 0.2346(2) 0.0276(9) Uani 1 1 d . . . . .
C008 C -0.1194(7) 0.1089(7) 0.1112(2) 0.0319(10) Uani 1 1 d . . . . .
C009 C 0.7287(7) 0.6082(6) 0.1291(2) 0.0307(10) Uani 1 1 d . . . . .
H009 H 0.8543 0.6365 0.1085 0.037 Uiso 1 1 calc R U . . .
C010 C 0.5650(6) 0.6544(6) 0.0843(2) 0.0289(9) Uani 1 1 d . . . . .
H010 H 0.5770 0.7150 0.0333 0.035 Uiso 1 1 calc R U . . .
C011 C 0.3605(7) 0.5274(6) 0.1886(2) 0.0303(10) Uani 1 1 d . . . . .
H011 H 0.2336 0.5006 0.2085 0.036 Uiso 1 1 calc R U . . .
C012 C 0.0755(7) 0.1573(6) 0.0849(2) 0.0337(10) Uani 1 1 d . . . . .
H012 H 0.0914 0.2203 0.0345 0.040 Uiso 1 1 calc R U . . .
C013 C -0.1390(7) 0.0141(6) 0.1900(2) 0.0310(10) Uani 1 1 d . . . . .
H013 H -0.2637 -0.0170 0.2090 0.037 Uiso 1 1 calc R U . . .
C014 C 0.0160(7) -0.0289(6) 0.2352(2) 0.0333(10) Uani 1 1 d . . . . .
H014 H -0.0001 -0.0915 0.2856 0.040 Uiso 1 1 calc R U . . .
C015 C 0.7130(7) 0.5206(7) 0.2040(2) 0.0285(9) Uani 1 1 d . . . . .
C016 C 0.7321(7) 0.2145(6) 0.4913(2) 0.0325(10) Uani 1 1 d . . . . .
H016 H 0.8821 0.1949 0.4803 0.039 Uiso 1 1 calc R U . . .
N1 N 0.6653(5) 0.3403(5) 0.35748(18) 0.0280(8) Uani 1 1 d . . . . .
C018 C 0.4244(7) 0.1992(6) 0.5805(2) 0.0331(10) Uani 1 1 d . . . . .
H018 H 0.3658 0.1702 0.6317 0.040 Uiso 1 1 calc R U . . .
C019 C 0.2293(7) 0.1151(6) 0.1299(2) 0.0319(10) Uani 1 1 d . . . . .
H019 H 0.3531 0.1478 0.1111 0.038 Uiso 1 1 calc R U . . .
C020 C 0.3821(7) 0.6122(6) 0.1140(2) 0.0283(9) Uani 1 1 d . . . . .
C022 C 0.5971(7) 0.2883(6) 0.4334(2) 0.0285(9) Uani 1 1 d . . . . .
C023 C 0.2902(7) 0.2683(6) 0.5237(2) 0.0313(10) Uani 1 1 d . . . . .
H023 H 0.1409 0.2856 0.5351 0.038 Uiso 1 1 calc R U . . .
C024 C 0.5048(7) 0.4029(6) 0.3157(2) 0.0297(10) Uani 1 1 d . . . . .
C025 C 0.3783(7) 0.3127(6) 0.4486(2) 0.0293(10) Uani 1 1 d . . . . .
C026 C 0.6444(7) 0.1705(6) 0.5649(2) 0.0319(10) Uani 1 1 d . . . . .
H026 H 0.7341 0.1205 0.6051 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 C024 1.756(4) . ?
S1 C025 1.726(4) . ?
O002 C006 1.226(5) . ?
O003 C008 1.227(5) . ?
O004 H004 0.8400 . ?
O004 C020 1.376(4) . ?
O005 H005 0.8400 . ?
O005 C015 1.359(4) . ?
C006 C014 1.473(6) . ?
C006 C019 1.478(5) . ?
C007 C011 1.398(5) . ?
C007 C015 1.403(5) . ?
C007 C024 1.468(5) . ?
C008 C012 1.476(6) . ?
C008 C013 1.471(5) . ?
C009 H009 0.9500 . ?
C009 C010 1.373(5) . ?
C009 C015 1.391(5) . ?
C010 H010 0.9500 . ?
C010 C020 1.386(5) . ?
C011 H011 0.9500 . ?
C011 C020 1.382(5) . ?
C012 H012 0.9500 . ?
C012 C019 1.328(5) . ?
C013 H013 0.9500 . ?
C013 C014 1.335(5) . ?
C014 H014 0.9500 . ?
C016 H016 0.9500 . ?
C016 C022 1.393(5) . ?
C016 C026 1.378(5) . ?
N1 C022 1.387(4) . ?
N1 C024 1.307(5) . ?
C018 H018 0.9500 . ?
C018 C023 1.373(5) . ?
C018 C026 1.393(6) . ?
C019 H019 0.9500 . ?
C022 C025 1.394(6) . ?
C023 H023 0.9500 . ?
C023 C025 1.402(5) . ?
C026 H026 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
C025 S1 C024 89.02(18) . . ?
C020 O004 H004 109.5 . . ?
C015 O005 H005 109.5 . . ?
O002 C006 C014 121.9(4) . . ?
O002 C006 C019 120.9(4) . . ?
C014 C006 C019 117.1(4) . . ?
C011 C007 C015 119.4(4) . . ?
C011 C007 C024 121.8(3) . . ?
C015 C007 C024 118.7(3) . . ?
O003 C008 C012 121.6(4) . . ?
O003 C008 C013 121.0(4) . . ?
C013 C008 C012 117.4(4) . . ?
C010 C009 H009 119.6 . . ?
C010 C009 C015 120.9(4) . . ?
C015 C009 H009 119.6 . . ?
C009 C010 H010 120.2 . . ?
C009 C010 C020 119.7(4) . . ?
C020 C010 H010 120.2 . . ?
C007 C011 H011 120.1 . . ?
C020 C011 C007 119.7(4) . . ?
C020 C011 H011 120.1 . . ?
C008 C012 H012 119.2 . . ?
C019 C012 C008 121.6(4) . . ?
C019 C012 H012 119.2 . . ?
C008 C013 H013 119.5 . . ?
C014 C013 C008 120.9(4) . . ?
C014 C013 H013 119.5 . . ?
C006 C014 H014 119.1 . . ?
C013 C014 C006 121.7(4) . . ?
C013 C014 H014 119.1 . . ?
O005 C015 C007 123.0(4) . . ?
O005 C015 C009 117.5(4) . . ?
C009 C015 C007 119.5(4) . . ?
C022 C016 H016 120.6 . . ?
C026 C016 H016 120.6 . . ?
C026 C016 C022 118.9(4) . . ?
C024 N1 C022 111.0(3) . . ?
C023 C018 H018 119.2 . . ?
C023 C018 C026 121.6(4) . . ?
C026 C018 H018 119.2 . . ?
C006 C019 H019 119.4 . . ?
C012 C019 C006 121.2(4) . . ?
C012 C019 H019 119.4 . . ?
O004 C020 C010 122.0(3) . . ?
O004 C020 C011 117.1(3) . . ?
C011 C020 C010 120.8(4) . . ?
C016 C022 C025 120.9(3) . . ?
N1 C022 C016 124.3(4) . . ?
N1 C022 C025 114.8(4) . . ?
C018 C023 H023 120.7 . . ?
C018 C023 C025 118.6(4) . . ?
C025 C023 H023 120.7 . . ?
C007 C024 S1 122.1(3) . . ?
N1 C024 S1 115.0(3) . . ?
N1 C024 C007 122.8(3) . . ?
C022 C025 S1 110.2(3) . . ?
C022 C025 C023 119.8(4) . . ?
C023 C025 S1 130.1(3) . . ?
C016 C026 C018 120.2(4) . . ?
C016 C026 H026 119.9 . . ?
C018 C026 H026 119.9 . . ?

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
O002 C006 C014 C013 178.1(4) . . . . ?
O002 C006 C019 C012 -178.3(4) . . . . ?
O003 C008 C012 C019 -178.3(4) . . . . ?
O003 C008 C013 C014 178.1(4) . . . . ?
C007 C011 C020 O004 -179.0(3) . . . . ?
C007 C011 C020 C010 -0.7(6) . . . . ?
C008 C012 C019 C006 -0.3(6) . . . . ?
C008 C013 C014 C006 0.7(6) . . . . ?
C009 C010 C020 O004 179.3(3) . . . . ?
C009 C010 C020 C011 1.1(6) . . . . ?
C010 C009 C015 O005 179.4(3) . . . . ?
C010 C009 C015 C007 -0.8(6) . . . . ?
C011 C007 C015 O005 -179.1(4) . . . . ?
C011 C007 C015 C009 1.2(6) . . . . ?
C011 C007 C024 S1 -10.8(5) . . . . ?
C011 C007 C024 N1 173.3(4) . . . . ?
C012 C008 C013 C014 -1.0(6) . . . . ?
C013 C008 C012 C019 0.8(6) . . . . ?
C014 C006 C019 C012 -0.1(6) . . . . ?
C015 C007 C011 C020 -0.4(6) . . . . ?
C015 C007 C024 S1 165.8(3) . . . . ?
C015 C007 C024 N1 -10.1(6) . . . . ?
C015 C009 C010 C020 -0.4(6) . . . . ?
C016 C022 C025 S1 -179.0(3) . . . . ?
C016 C022 C025 C023 1.9(6) . . . . ?
N1 C022 C025 S1 0.2(4) . . . . ?
N1 C022 C025 C023 -178.9(3) . . . . ?
C018 C023 C025 S1 -179.6(3) . . . . ?
C018 C023 C025 C022 -0.7(6) . . . . ?
C019 C006 C014 C013 -0.1(6) . . . . ?
C022 C016 C026 C018 0.2(6) . . . . ?
C022 N1 C024 S1 -0.4(4) . . . . ?
C022 N1 C024 C007 175.7(3) . . . . ?
C023 C018 C026 C016 1.0(6) . . . . ?
C024 S1 C025 C022 -0.4(3) . . . . ?
C024 S1 C025 C023 178.6(4) . . . . ?
C024 C007 C011 C020 176.2(4) . . . . ?
C024 C007 C015 O005 4.2(6) . . . . ?
C024 C007 C015 C009 -175.6(4) . . . . ?
C024 N1 C022 C016 179.4(4) . . . . ?
C024 N1 C022 C025 0.1(5) . . . . ?
C025 S1 C024 C007 -175.7(3) . . . . ?
C025 S1 C024 N1 0.5(3) . . . . ?
C026 C016 C022 N1 179.2(4) . . . . ?
C026 C016 C022 C025 -1.6(6) . . . . ?
C026 C018 C023 C025 -0.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
