# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_compound2b
_database_code_depnum_ccdc_archive 'CCDC 2193290'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 N2 O2 S2'
_chemical_formula_weight         484.61

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   7.927(2)
_cell_length_b                   18.115(5)
_cell_length_c                   16.886(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.357(16)
_cell_angle_gamma                90.00
_cell_volume                     2414.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8472
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.43

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30128
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         28.29
_reflns_number_total             5971
_reflns_number_gt                3709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5971
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   0.732
_refine_ls_restrained_S_all      0.732
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S2 S 0.64500(6) 0.09346(2) 0.86892(3) 0.04204(15) Uani 1 1 d . . .
N2 N 0.7467(2) 0.30765(8) 0.76912(11) 0.0425(4) Uani 1 1 d . . .
H15 H 0.7384 0.3129 0.7183 0.051 Uiso 1 1 calc R . .
C22 C 0.8368(3) 0.36276(10) 0.81961(13) 0.0454(5) Uani 1 1 d . . .
H22A H 0.9271 0.3832 0.7914 0.054 Uiso 1 1 calc R . .
H22B H 0.8889 0.3384 0.8669 0.054 Uiso 1 1 calc R . .
S1 S 0.63906(6) -0.01948(3) 0.86953(3) 0.04166(15) Uani 1 1 d . . .
O2 O 0.67781(18) 0.24065(8) 0.87399(9) 0.0471(4) Uani 1 1 d . . .
O1 O 0.6592(2) -0.16734(8) 0.89270(10) 0.0513(4) Uani 1 1 d . . .
C23 C 0.7283(3) 0.42548(10) 0.84500(13) 0.0429(5) Uani 1 1 d . . .
C9 C 0.7424(3) -0.26330(11) 1.09432(15) 0.0532(6) Uani 1 1 d . . .
C28 C 0.5954(3) 0.45341(11) 0.79532(15) 0.0518(5) Uani 1 1 d . . .
H28 H 0.5667 0.4314 0.7461 0.062 Uiso 1 1 calc R . .
N1 N 0.5275(2) -0.21921(9) 0.99252(11) 0.0503(4) Uani 1 1 d . . .
H1 H 0.4399 -0.2181 1.0189 0.060 Uiso 1 1 calc R . .
C16 C 0.4873(3) 0.07053(11) 0.71624(13) 0.0477(5) Uani 1 1 d . . .
H16 H 0.4714 0.0221 0.7321 0.057 Uiso 1 1 calc R . .
C17 C 0.4286(3) 0.09197(12) 0.64029(14) 0.0562(6) Uani 1 1 d . . .
H17 H 0.3722 0.0582 0.6058 0.067 Uiso 1 1 calc R . .
C3 C 0.1379(3) -0.01123(12) 0.90516(15) 0.0515(5) Uani 1 1 d . . .
H3 H 0.0511 0.0235 0.8997 0.062 Uiso 1 1 calc R . .
C4 C 0.1047(3) -0.08160(12) 0.93129(13) 0.0498(5) Uani 1 1 d . . .
H4 H -0.0043 -0.0950 0.9417 0.060 Uiso 1 1 calc R . .
C18 C 0.4532(3) 0.16358(12) 0.61500(14) 0.0572(6) Uani 1 1 d . . .
H18 H 0.4147 0.1779 0.5636 0.069 Uiso 1 1 calc R . .
C19 C 0.5352(3) 0.21319(11) 0.66700(13) 0.0490(5) Uani 1 1 d . . .
H19 H 0.5515 0.2613 0.6501 0.059 Uiso 1 1 calc R . .
C20 C 0.5946(2) 0.19323(10) 0.74448(12) 0.0383(4) Uani 1 1 d . . .
C2 C 0.2982(3) 0.00804(11) 0.88718(13) 0.0450(5) Uani 1 1 d . . .
H2 H 0.3179 0.0555 0.8690 0.054 Uiso 1 1 calc R . .
C5 C 0.2363(3) -0.13166(11) 0.94172(12) 0.0438(5) Uani 1 1 d . . .
H5 H 0.2151 -0.1787 0.9605 0.053 Uiso 1 1 calc R . .
C6 C 0.4004(2) -0.11358(9) 0.92482(11) 0.0350(4) Uani 1 1 d . . .
C7 C 0.5405(3) -0.16892(9) 0.93527(12) 0.0381(4) Uani 1 1 d . . .
C15 C 0.5696(2) 0.12010(10) 0.76938(12) 0.0378(4) Uani 1 1 d . . .
C21 C 0.6765(2) 0.24876(10) 0.80120(12) 0.0379(4) Uani 1 1 d . . .
C1 C 0.4309(2) -0.04236(9) 0.89574(11) 0.0362(4) Uani 1 1 d . . .
C12 C 0.8799(5) -0.2348(3) 1.2487(2) 0.1094(15) Uani 1 1 d . . .
H12 H 0.9244 -0.2246 1.3004 0.131 Uiso 1 1 calc R . .
C11 C 0.7775(4) -0.2951(2) 1.2330(2) 0.0944(11) Uani 1 1 d . . .
H11 H 0.7541 -0.3265 1.2741 0.113 Uiso 1 1 calc R . .
C13 C 0.9160(4) -0.18955(19) 1.1866(3) 0.0945(11) Uani 1 1 d . . .
H13 H 0.9870 -0.1491 1.1965 0.113 Uiso 1 1 calc R . .
C26 C 0.5465(4) 0.54688(16) 0.8899(2) 0.0852(10) Uani 1 1 d . . .
H26 H 0.4858 0.5877 0.9048 0.102 Uiso 1 1 calc R . .
C25 C 0.6777(5) 0.51992(17) 0.9399(2) 0.0882(10) Uani 1 1 d . . .
H25 H 0.7064 0.5424 0.9888 0.106 Uiso 1 1 calc R . .
C14 C 0.8482(4) -0.20371(14) 1.1106(2) 0.0729(8) Uani 1 1 d . . .
H14 H 0.8737 -0.1728 1.0695 0.088 Uiso 1 1 calc R . .
C10 C 0.7090(3) -0.30943(16) 1.15607(17) 0.0675(7) Uani 1 1 d . . .
H10 H 0.6399 -0.3505 1.1459 0.081 Uiso 1 1 calc R . .
C8 C 0.6556(4) -0.27567(12) 1.01203(15) 0.0642(7) Uani 1 1 d . . .
H8A H 0.7388 -0.2744 0.9735 0.077 Uiso 1 1 calc R . .
H8B H 0.6026 -0.3240 1.0094 0.077 Uiso 1 1 calc R . .
C27 C 0.5047(3) 0.51365(13) 0.81788(18) 0.0670(7) Uani 1 1 d . . .
H27 H 0.4148 0.5317 0.7841 0.080 Uiso 1 1 calc R . .
C24 C 0.7681(4) 0.45898(13) 0.91759(16) 0.0647(7) Uani 1 1 d . . .
H24 H 0.8565 0.4405 0.9520 0.078 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C15 1.797(2) . ?
S2 S1 2.0465(9) . ?
N2 C21 1.341(2) . ?
N2 C22 1.456(2) . ?
N2 H15 0.8600 . ?
C22 C23 1.511(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
S1 C1 1.797(2) . ?
O2 C21 1.237(2) . ?
O1 C7 1.236(3) . ?
C23 C24 1.378(3) . ?
C23 C28 1.380(3) . ?
C9 C14 1.379(4) . ?
C9 C10 1.381(3) . ?
C9 C8 1.509(3) . ?
C28 C27 1.380(3) . ?
C28 H28 0.9300 . ?
N1 C7 1.339(3) . ?
N1 C8 1.457(3) . ?
N1 H1 0.8600 . ?
C16 C17 1.379(3) . ?
C16 C15 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C3 C2 1.379(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(3) . ?
C19 H19 0.9300 . ?
C20 C15 1.409(2) . ?
C20 C21 1.495(3) . ?
C2 C1 1.390(3) . ?
C2 H2 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.409(2) . ?
C6 C7 1.495(3) . ?
C12 C11 1.372(5) . ?
C12 C13 1.382(6) . ?
C12 H12 0.9300 . ?
C11 C10 1.384(4) . ?
C11 H11 0.9300 . ?
C13 C14 1.368(5) . ?
C13 H13 0.9300 . ?
C26 C25 1.367(5) . ?
C26 C27 1.370(4) . ?
C26 H26 0.9300 . ?
C25 C24 1.387(4) . ?
C25 H25 0.9300 . ?
C14 H14 0.9300 . ?
C10 H10 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C27 H27 0.9300 . ?
C24 H24 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
C15 S2 S1 105.51(6) . . ?
C21 N2 C22 120.56(18) . . ?
C21 N2 H15 119.7 . . ?
C22 N2 H15 119.7 . . ?
N2 C22 C23 114.84(16) . . ?
N2 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
N2 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.5 . . ?
C1 S1 S2 104.71(6) . . ?
C24 C23 C28 118.5(2) . . ?
C24 C23 C22 119.62(19) . . ?
C28 C23 C22 121.7(2) . . ?
C14 C9 C10 118.6(3) . . ?
C14 C9 C8 121.1(2) . . ?
C10 C9 C8 120.2(2) . . ?
C27 C28 C23 120.7(2) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
C7 N1 C8 122.8(2) . . ?
C7 N1 H1 118.6 . . ?
C8 N1 H1 118.6 . . ?
C17 C16 C15 121.08(19) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 121.78(19) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C15 118.59(17) . . ?
C19 C20 C21 120.96(17) . . ?
C15 C20 C21 120.40(18) . . ?
C3 C2 C1 120.98(19) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C5 C6 121.80(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.63(17) . . ?
C5 C6 C7 120.99(17) . . ?
C1 C6 C7 120.36(17) . . ?
O1 C7 N1 123.32(18) . . ?
O1 C7 C6 120.89(17) . . ?
N1 C7 C6 115.79(19) . . ?
C16 C15 C20 119.06(18) . . ?
C16 C15 S2 121.74(15) . . ?
C20 C15 S2 119.20(14) . . ?
O2 C21 N2 122.05(18) . . ?
O2 C21 C20 121.30(17) . . ?
N2 C21 C20 116.64(18) . . ?
C2 C1 C6 119.01(18) . . ?
C2 C1 S1 121.75(15) . . ?
C6 C1 S1 119.23(14) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C13 C14 C9 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
N1 C8 C9 110.64(18) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C26 C27 C28 120.2(2) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_compound2n
_database_code_depnum_ccdc_archive 'CCDC 2193296'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 N4 O3 S2'
_chemical_formula_weight         518.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9627(17)
_cell_length_b                   9.6003(15)
_cell_length_c                   15.312(3)
_cell_angle_alpha                101.184(13)
_cell_angle_beta                 95.225(12)
_cell_angle_gamma                101.995(12)
_cell_volume                     1252.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    940
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      18.18

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             434
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13798
_diffrn_reflns_av_unetI/netI     0.1453
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.222
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4890
_reflns_number_gt                2514
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4890
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1499
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2096
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.928
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.93136(15) 0.68263(13) 0.94176(8) 0.0351(3) Uani 1 1 d . . . . .
S1 S 0.98567(14) 0.68975(14) 1.07448(8) 0.0361(4) Uani 1 1 d . . . . .
C20 C 0.9099(6) 0.8380(5) 0.7888(3) 0.0311(11) Uani 1 1 d . . . . .
C7 C 0.9809(5) 0.6420(5) 1.2603(3) 0.0308(11) Uani 1 1 d . . . . .
C14 C 0.8331(5) 0.8920(5) 0.8669(3) 0.0284(10) Uani 1 1 d . . . . .
C1 C 0.8323(5) 0.5649(4) 1.1041(3) 0.0282(10) Uani 1 1 d . . . . .
C15 C 0.8388(5) 0.8306(5) 0.9420(3) 0.0290(11) Uani 1 1 d . . . . .
C16 C 0.7024(5) 1.0025(5) 1.0142(4) 0.0373(12) Uani 1 1 d . . . . .
H16 H 0.660295 1.042408 1.065477 0.045 Uiso 1 1 calc R U . . .
C17 C 0.7577(6) 1.0043(5) 0.8653(3) 0.0367(12) Uani 1 1 d . . . . .
H17 H 0.752231 1.044313 0.813354 0.044 Uiso 1 1 calc R U . . .
C21 C 1.0644(5) 0.8910(5) 0.6719(3) 0.0350(11) Uani 1 1 d . . . . .
H21A H 1.120691 0.816723 0.683810 0.042 Uiso 1 1 calc R U . . .
H21B H 1.140719 0.976604 0.663744 0.042 Uiso 1 1 calc R U . . .
C2 C 0.7061(5) 0.4805(5) 1.0440(3) 0.0358(12) Uani 1 1 d . . . . .
H2 H 0.694381 0.491921 0.983650 0.043 Uiso 1 1 calc R U . . .
C18 C 0.7745(5) 0.8893(5) 1.0165(3) 0.0336(11) Uani 1 1 d . . . . .
H18 H 0.780565 0.851002 1.069151 0.040 Uiso 1 1 calc R U . . .
C10 C 1.4072(6) 0.8693(6) 1.3508(4) 0.0429(13) Uani 1 1 d . . . . .
H10 H 1.377173 0.923178 1.402381 0.051 Uiso 1 1 calc R U . . .
C23 C 0.9311(6) 0.6870(5) 0.5410(3) 0.0394(12) Uani 1 1 d . . . . .
H23 H 0.987444 0.625122 0.563803 0.047 Uiso 1 1 calc R U . . .
C22 C 0.9532(5) 0.8294(5) 0.5868(3) 0.0306(11) Uani 1 1 d . . . . .
C3 C 0.8492(5) 0.5466(5) 1.1933(3) 0.0300(11) Uani 1 1 d . . . . .
C24 C 0.8690(6) 0.9157(5) 0.5508(4) 0.0408(13) Uani 1 1 d . . . . .
H24 H 0.882095 1.014492 0.581151 0.049 Uiso 1 1 calc R U . . .
C19 C 0.6910(6) 1.0582(5) 0.9379(4) 0.0408(13) Uani 1 1 d . . . . .
H19 H 0.637346 1.133243 0.935620 0.049 Uiso 1 1 calc R U . . .
C9 C 1.3308(5) 0.7230(5) 1.3208(3) 0.0339(11) Uani 1 1 d . . . . .
C11 C 1.3772(6) 0.6469(6) 1.2456(3) 0.0456(14) Uani 1 1 d . . . . .
H11 H 1.328270 0.547199 1.221582 0.055 Uiso 1 1 calc R U . . .
C25 C 0.7695(5) 0.8648(5) 0.4745(3) 0.0356(12) Uani 1 1 d . . . . .
H25 H 0.713345 0.926137 0.450950 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7408(6) 0.4404(5) 1.2183(4) 0.0385(12) Uani 1 1 d . . . . .
H4 H 0.753524 0.424446 1.277580 0.046 Uiso 1 1 calc R U . . .
C8 C 1.2043(6) 0.6548(5) 1.3670(3) 0.0377(12) Uani 1 1 d . . . . .
H8A H 1.241719 0.587738 1.400691 0.045 Uiso 1 1 calc R U . . .
H8B H 1.176124 0.732076 1.410886 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6145(6) 0.3577(5) 1.1577(4) 0.0429(13) Uani 1 1 d . . . . .
H5 H 0.540344 0.286262 1.175517 0.052 Uiso 1 1 calc R U . . .
C26 C 0.7519(6) 0.7270(6) 0.4332(4) 0.0507(15) Uani 1 1 d . . . . .
H26 H 0.681117 0.691612 0.379477 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5972(6) 0.3795(5) 1.0719(4) 0.0414(13) Uani 1 1 d . . . . .
H6 H 0.509260 0.324471 1.030890 0.050 Uiso 1 1 calc R U . . .
C13 C 1.5601(6) 0.8606(6) 1.2404(4) 0.0476(14) Uani 1 1 d . . . . .
H13 H 1.639261 0.907739 1.211632 0.057 Uiso 1 1 calc R U . . .
C12 C 1.4945(6) 0.7160(6) 1.2056(4) 0.0509(15) Uani 1 1 d . . . . .
H12 H 1.528979 0.664194 1.154984 0.061 Uiso 1 1 calc R U . . .
O1 O 1.0055(4) 0.7770(3) 1.2746(2) 0.0377(8) Uani 1 1 d . . . . .
O2 O 0.9012(4) 0.7044(3) 0.7645(2) 0.0425(9) Uani 1 1 d . . . . .
N1 N 1.0671(5) 0.5736(4) 1.3038(3) 0.0342(10) Uani 1 1 d . . . . .
N3 N 0.9874(5) 0.9353(4) 0.7495(3) 0.0306(9) Uani 1 1 d . . . . .
N2 N 1.5192(5) 0.9398(5) 1.3127(3) 0.0458(11) Uani 1 1 d . . . . .
N4 N 0.8286(6) 0.6314(5) 0.4624(3) 0.0615(14) Uani 1 1 d . . . . .
O3 O 0.6283(6) 0.2521(5) 0.3763(4) 0.0961(17) Uani 1 1 d . . . . .
H3 H 0.630330 0.188875 0.407052 0.144 Uiso 1 1 calc R U . . .
C27 C 0.4993(9) 0.3072(7) 0.3877(6) 0.101(3) Uani 1 1 d . . . . .
H27A H 0.461641 0.288279 0.443388 0.152 Uiso 1 1 calc R U . . .
H27B H 0.418852 0.259870 0.336674 0.152 Uiso 1 1 calc R U . . .
H27C H 0.525648 0.412654 0.391239 0.152 Uiso 1 1 calc R U . . .
H7 H 0.987(6) 1.031(5) 0.767(3) 0.045(15) Uiso 1 1 d . . . . .
H1 H 1.051(6) 0.482(6) 1.289(4) 0.060(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C15 1.787(4) . ?
S2 S1 2.0306(18) . ?
S1 C1 1.781(5) . ?
C20 O2 1.249(5) . ?
C20 N3 1.319(6) . ?
C20 C14 1.494(6) . ?
C7 O1 1.241(5) . ?
C7 N1 1.325(6) . ?
C7 C3 1.500(6) . ?
C14 C17 1.389(6) . ?
C14 C15 1.392(6) . ?
C1 C2 1.387(6) . ?
C1 C3 1.409(6) . ?
C15 C18 1.399(6) . ?
C16 C18 1.379(6) . ?
C16 C19 1.380(7) . ?
C17 C19 1.374(6) . ?
C21 N3 1.464(6) . ?
C21 C22 1.503(6) . ?
C2 C6 1.385(7) . ?
C10 N2 1.336(6) . ?
C10 C9 1.395(7) . ?
C23 C22 1.375(6) . ?
C23 N4 1.386(7) . ?
C22 C24 1.386(6) . ?
C3 C4 1.392(6) . ?
C24 C25 1.344(7) . ?
C9 C11 1.386(7) . ?
C9 C8 1.494(7) . ?
C11 C12 1.380(7) . ?
C25 C26 1.321(7) . ?
C4 C5 1.387(7) . ?
C8 N1 1.466(6) . ?
C5 C6 1.370(7) . ?
C26 N4 1.371(7) . ?
C13 N2 1.341(7) . ?
C13 C12 1.369(7) . ?
O3 C27 1.379(7) . ?

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
C15 S2 S1 103.33(16) . . ?
C1 S1 S2 106.27(17) . . ?
O2 C20 N3 122.7(4) . . ?
O2 C20 C14 119.3(4) . . ?
N3 C20 C14 118.0(4) . . ?
O1 C7 N1 122.4(5) . . ?
O1 C7 C3 121.4(4) . . ?
N1 C7 C3 116.2(4) . . ?
C17 C14 C15 120.0(4) . . ?
C17 C14 C20 120.3(4) . . ?
C15 C14 C20 119.8(4) . . ?
C2 C1 C3 119.6(4) . . ?
C2 C1 S1 124.0(4) . . ?
C3 C1 S1 116.2(3) . . ?
C14 C15 C18 118.6(4) . . ?
C14 C15 S2 119.4(3) . . ?
C18 C15 S2 122.0(4) . . ?
C18 C16 C19 120.4(5) . . ?
C19 C17 C14 120.8(5) . . ?
N3 C21 C22 112.4(4) . . ?
C6 C2 C1 120.0(5) . . ?
C16 C18 C15 120.5(5) . . ?
N2 C10 C9 125.2(5) . . ?
C22 C23 N4 121.6(5) . . ?
C23 C22 C24 117.1(5) . . ?
C23 C22 C21 122.1(4) . . ?
C24 C22 C21 120.8(4) . . ?
C4 C3 C1 119.0(4) . . ?
C4 C3 C7 120.8(4) . . ?
C1 C3 C7 120.2(4) . . ?
C25 C24 C22 122.5(5) . . ?
C17 C19 C16 119.5(4) . . ?
C11 C9 C10 116.2(5) . . ?
C11 C9 C8 122.6(5) . . ?
C10 C9 C8 121.2(5) . . ?
C12 C11 C9 119.9(5) . . ?
C26 C25 C24 118.1(5) . . ?
C5 C4 C3 120.7(5) . . ?
N1 C8 C9 112.3(4) . . ?
C6 C5 C4 119.6(5) . . ?
C25 C26 N4 124.7(5) . . ?
C5 C6 C2 121.0(5) . . ?
N2 C13 C12 123.9(5) . . ?
C13 C12 C11 118.7(5) . . ?
C7 N1 C8 121.2(4) . . ?
C20 N3 C21 121.3(4) . . ?
C10 N2 C13 116.0(5) . . ?
C26 N4 C23 116.0(5) . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.080


####################################################################### 
# 
# 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_compound2i
_database_code_depnum_ccdc_archive 'CCDC 2193294'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 N4 O2 S2'
_chemical_formula_weight         446.62

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.767(3)
_cell_length_b                   19.185(6)
_cell_length_c                   15.494(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.481(6)
_cell_angle_gamma                90
_cell_volume                     2289.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    860
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      19.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.258
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14771
_diffrn_reflns_av_unetI/netI     0.1292
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.123
_diffrn_reflns_theta_max         28.790
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5928
_reflns_number_gt                3154
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5928
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1964
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_restrained_S_all      0.887
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.17058(11) 0.08851(4) 0.36077(6) 0.0276(2) Uani 1 1 d . . . . .
S1 S 0.18974(11) -0.01768(4) 0.36447(6) 0.0287(2) Uani 1 1 d . . . . .
C7 C 0.1225(4) -0.15478(17) 0.4519(2) 0.0255(7) Uani 1 1 d . . . . .
C1 C -0.0193(4) -0.04599(17) 0.3876(2) 0.0246(7) Uani 1 1 d . . . . .
C12 C 0.0933(4) 0.18052(17) 0.2246(2) 0.0265(7) Uani 1 1 d . . . . .
C18 C 0.1388(4) 0.23674(18) 0.2904(2) 0.0268(7) Uani 1 1 d . . . . .
C13 C 0.0975(4) 0.11001(18) 0.2500(2) 0.0262(7) Uani 1 1 d . . . . .
C2 C -0.1986(4) -0.13458(19) 0.4407(2) 0.0295(8) Uani 1 1 d . . . . .
H2 H -0.210380 -0.179701 0.464528 0.035 Uiso 1 1 calc R U . . .
C14 C 0.0406(5) 0.1968(2) 0.1373(2) 0.0348(8) Uani 1 1 d . . . . .
H14 H 0.035914 0.244278 0.119557 0.042 Uiso 1 1 calc R U . . .
C3 C -0.0347(4) -0.11114(17) 0.4259(2) 0.0249(7) Uani 1 1 d . . . . .
C4 C -0.3433(4) -0.0932(2) 0.4213(2) 0.0345(9) Uani 1 1 d . . . . .
H4 H -0.454546 -0.109918 0.430665 0.041 Uiso 1 1 calc R U . . .
C19 C 0.2355(5) 0.35649(17) 0.3204(2) 0.0312(8) Uani 1 1 d . . . . .
H19A H 0.333632 0.381207 0.299116 0.037 Uiso 1 1 calc R U . . .
H19B H 0.277692 0.337426 0.378695 0.037 Uiso 1 1 calc R U . . .
C5 C -0.1654(4) -0.00348(19) 0.3701(2) 0.0307(8) Uani 1 1 d . . . . .
H5 H -0.155377 0.041641 0.346024 0.037 Uiso 1 1 calc R U . . .
C6 C -0.3251(5) -0.0274(2) 0.3882(2) 0.0361(9) Uani 1 1 d . . . . .
H6 H -0.423882 0.002052 0.377489 0.043 Uiso 1 1 calc R U . . .
C15 C -0.0046(5) 0.1456(2) 0.0764(3) 0.0421(10) Uani 1 1 d . . . . .
H15 H -0.037511 0.157644 0.017070 0.051 Uiso 1 1 calc R U . . .
C9 C 0.3963(5) -0.1919(2) 0.6342(3) 0.0410(10) Uani 1 1 d . . . . .
H9A H 0.506738 -0.217965 0.646424 0.049 Uiso 1 1 calc R U . . .
H9B H 0.423563 -0.144968 0.612970 0.049 Uiso 1 1 calc R U . . .
C20 C 0.0919(5) 0.40862(19) 0.3292(2) 0.0363(9) Uani 1 1 d . . . . .
H20A H 0.143954 0.450856 0.358704 0.044 Uiso 1 1 calc R U . . .
H20B H 0.038216 0.422524 0.270290 0.044 Uiso 1 1 calc R U . . .
C16 C 0.0501(5) 0.0589(2) 0.1879(2) 0.0337(8) Uani 1 1 d . . . . .
H16 H 0.053538 0.011188 0.204495 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2795(5) -0.2289(2) 0.5642(2) 0.0396(10) Uani 1 1 d . . . . .
H8A H 0.347696 -0.241877 0.516901 0.047 Uiso 1 1 calc R U . . .
H8B H 0.237683 -0.272532 0.588559 0.047 Uiso 1 1 calc R U . . .
C10 C 0.3160(5) -0.2515(2) 0.7586(3) 0.0484(11) Uani 1 1 d . . . . .
H10A H 0.434100 -0.270262 0.769761 0.073 Uiso 1 1 calc R U . . .
H10B H 0.241922 -0.284062 0.721811 0.073 Uiso 1 1 calc R U . . .
H10C H 0.269577 -0.245134 0.813927 0.073 Uiso 1 1 calc R U . . .
C17 C -0.0021(5) 0.0771(2) 0.1018(2) 0.0433(10) Uani 1 1 d . . . . .
H17 H -0.036286 0.041775 0.060049 0.052 Uiso 1 1 calc R U . . .
C21 C 0.0191(6) 0.3758(2) 0.4698(3) 0.0527(12) Uani 1 1 d . . . . .
H21A H -0.077699 0.363068 0.501406 0.079 Uiso 1 1 calc R U . . .
H21B H 0.068766 0.420253 0.492100 0.079 Uiso 1 1 calc R U . . .
H21C H 0.108363 0.339481 0.477994 0.079 Uiso 1 1 calc R U . . .
C11 C 0.4144(6) -0.1338(2) 0.7722(3) 0.0549(12) Uani 1 1 d . . . . .
H11A H 0.420026 -0.089418 0.741351 0.082 Uiso 1 1 calc R U . . .
H11B H 0.532320 -0.150934 0.790534 0.082 Uiso 1 1 calc R U . . .
H11C H 0.354634 -0.126876 0.823460 0.082 Uiso 1 1 calc R U . . .
C22 C -0.1946(6) 0.4286(2) 0.3646(3) 0.0590(13) Uani 1 1 d . . . . .
H22A H -0.160753 0.475609 0.384808 0.089 Uiso 1 1 calc R U . . .
H22B H -0.284684 0.410796 0.397555 0.089 Uiso 1 1 calc R U . . .
H22C H -0.239825 0.430114 0.302507 0.089 Uiso 1 1 calc R U . . .
O1 O 0.2424(3) -0.15727(12) 0.40591(15) 0.0307(6) Uani 1 1 d . . . . .
O2 O 0.1415(3) 0.22459(12) 0.36918(15) 0.0298(6) Uani 1 1 d . . . . .
N3 N 0.1831(4) 0.29885(15) 0.2618(2) 0.0296(7) Uani 1 1 d . . . . .
N1 N 0.1310(4) -0.18808(16) 0.5277(2) 0.0314(7) Uani 1 1 d . . . . .
N4 N -0.0436(4) 0.38274(16) 0.3776(2) 0.0380(8) Uani 1 1 d . . . . .
N2 N 0.3193(4) -0.18465(17) 0.7144(2) 0.0389(8) Uani 1 1 d . . . . .
H3 H 0.193(5) 0.306(2) 0.209(3) 0.041(12) Uiso 1 1 d . . . . .
H1 H 0.047(6) -0.181(2) 0.560(3) 0.065(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C13 1.785(4) . ?
S2 S1 2.0429(14) . ?
S1 C1 1.792(3) . ?
C7 O1 1.245(4) . ?
C7 N1 1.330(4) . ?
C7 C3 1.492(5) . ?
C1 C5 1.395(5) . ?
C1 C3 1.396(4) . ?
C12 C14 1.397(5) . ?
C12 C13 1.408(5) . ?
C12 C18 1.495(5) . ?
C18 O2 1.241(4) . ?
C18 N3 1.332(4) . ?
C13 C16 1.389(5) . ?
C2 C4 1.376(5) . ?
C2 C3 1.397(4) . ?
C14 C15 1.376(5) . ?
C4 C6 1.377(5) . ?
C19 N3 1.455(4) . ?
C19 C20 1.517(5) . ?
C5 C6 1.385(5) . ?
C15 C17 1.372(5) . ?
C9 N2 1.454(4) . ?
C9 C8 1.499(6) . ?
C20 N4 1.457(5) . ?
C16 C17 1.388(5) . ?
C8 N1 1.447(5) . ?
C10 N2 1.455(5) . ?
C21 N4 1.454(5) . ?
C11 N2 1.458(5) . ?
C22 N4 1.458(5) . ?

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 S2 S1 105.68(12) . . ?
C1 S1 S2 104.08(11) . . ?
O1 C7 N1 122.1(3) . . ?
O1 C7 C3 120.9(3) . . ?
N1 C7 C3 116.9(3) . . ?
C5 C1 C3 119.6(3) . . ?
C5 C1 S1 121.3(3) . . ?
C3 C1 S1 119.1(2) . . ?
C14 C12 C13 118.6(3) . . ?
C14 C12 C18 120.8(3) . . ?
C13 C12 C18 120.5(3) . . ?
O2 C18 N3 121.5(3) . . ?
O2 C18 C12 120.5(3) . . ?
N3 C18 C12 117.9(3) . . ?
C16 C13 C12 119.4(3) . . ?
C16 C13 S2 121.7(3) . . ?
C12 C13 S2 118.9(3) . . ?
C4 C2 C3 120.9(3) . . ?
C15 C14 C12 121.4(4) . . ?
C1 C3 C2 119.2(3) . . ?
C1 C3 C7 120.3(3) . . ?
C2 C3 C7 120.4(3) . . ?
C2 C4 C6 119.3(3) . . ?
N3 C19 C20 114.1(3) . . ?
C6 C5 C1 119.6(3) . . ?
C4 C6 C5 121.2(3) . . ?
C17 C15 C14 119.7(4) . . ?
N2 C9 C8 112.7(3) . . ?
N4 C20 C19 114.2(3) . . ?
C17 C16 C13 120.4(4) . . ?
N1 C8 C9 113.7(3) . . ?
C15 C17 C16 120.5(4) . . ?
C18 N3 C19 122.4(3) . . ?
C7 N1 C8 123.4(3) . . ?
C21 N4 C20 111.4(3) . . ?
C21 N4 C22 110.6(3) . . ?
C20 N4 C22 110.2(3) . . ?
C9 N2 C10 110.7(3) . . ?
C9 N2 C11 110.9(3) . . ?
C10 N2 C11 109.8(3) . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.076


####################################################################### 
# 
# 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_compound2f
_database_code_depnum_ccdc_archive 'CCDC 2193293'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 N2 O4 S2'
_chemical_formula_weight         472.60

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'

_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'

_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.
;

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                   7.8446(2)
_cell_length_b                   15.3529(4)
_cell_length_c                   18.7689(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2260.48(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6786
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            colorlee
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31168
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.714
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5592
_reflns_number_gt                4754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1772 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5592
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3384(4) 0.84152(19) 1.07585(17) 0.0260(6) Uani 1 1 d . . . . .
C2 C 0.2467(4) 0.8823(2) 0.95830(16) 0.0289(6) Uani 1 1 d . . . . .
H4 H 0.2726 0.9006 0.9112 0.035 Uiso 1 1 calc R U . . .
C3 C 0.0384(4) 0.8429(2) 1.04610(19) 0.0335(7) Uani 1 1 d . . . . .
H3 H -0.0770 0.8340 1.0597 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3780(4) 0.86954(18) 1.00710(16) 0.0265(6) Uani 1 1 d . . . . .
C5 C 0.1684(4) 0.8302(2) 1.09480(18) 0.0297(6) Uani 1 1 d . . . . .
H5 H 0.1410 0.8134 1.1422 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0779(4) 0.8684(2) 0.97792(18) 0.0339(7) Uani 1 1 d . . . . .
H6 H -0.0105 0.8767 0.9440 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4762(4) 0.8256(2) 1.12930(18) 0.0323(7) Uani 1 1 d . . . . .
C10 C 0.7177(5) 0.6275(3) 1.3034(2) 0.0421(8) Uani 1 1 d . . . . .
H10A H 0.8423 0.6377 1.3034 0.051 Uiso 1 1 calc R U . A 1
H10B H 0.6678 0.6576 1.3451 0.051 Uiso 1 1 calc R U . A 1
C11 C 0.6807(5) 0.5303(2) 1.3073(2) 0.0424(9) Uani 1 1 d . . . . .
H11A H 0.7860 0.4968 1.3168 0.051 Uiso 1 1 calc R U . . .
H11B H 0.5960 0.5174 1.3449 0.051 Uiso 1 1 calc R U . . .
C12 C 0.6103(5) 0.5095(2) 1.2343(2) 0.0440(8) Uani 1 1 d . . . . .
H12A H 0.7023 0.4891 1.2024 0.053 Uiso 1 1 calc R U . . .
H12B H 0.5222 0.4635 1.2376 0.053 Uiso 1 1 calc R U . . .
C13 C 0.5715(4) 0.98715(19) 0.84399(17) 0.0275(6) Uani 1 1 d . . . . .
C14 C 0.5109(4) 1.0518(2) 0.88886(18) 0.0329(7) Uani 1 1 d . . . . .
H14 H 0.4882 1.0382 0.9373 0.039 Uiso 1 1 calc R U . . .
C15 C 0.4829(5) 1.1353(2) 0.8649(2) 0.0375(8) Uani 1 1 d . . . . .
H15 H 0.4401 1.1783 0.8966 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5171(4) 1.1565(2) 0.7950(2) 0.0362(8) Uani 1 1 d . . . . .
H16 H 0.4974 1.2140 0.7781 0.043 Uiso 1 1 calc R U . . .
C17 C 0.5802(4) 1.09350(19) 0.74971(18) 0.0318(7) Uani 1 1 d . . . . .
H17 H 0.6061 1.1086 0.7018 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6070(4) 1.00774(18) 0.77267(16) 0.0269(6) Uani 1 1 d . . . . .
C19 C 0.6610(4) 0.9385(2) 0.72161(18) 0.0291(6) Uani 1 1 d . . . . .
C20 C 0.7680(5) 0.9002(2) 0.6028(2) 0.0401(8) Uani 1 1 d . . . . .
H20A H 0.8901 0.9069 0.5908 0.048 Uiso 1 1 calc R U . B 1
H20B H 0.7521 0.8408 0.6222 0.048 Uiso 1 1 calc R U . B 1
C22 C 0.4861(8) 0.9111(4) 0.5351(3) 0.088(2) Uani 1 1 d . . . . .
H22A H 0.4471 0.9724 0.5353 0.106 Uiso 1 1 calc R U . C 1
H22B H 0.4366 0.8814 0.5771 0.106 Uiso 1 1 calc R U . C 1
C24 C 0.5834(7) 0.8164(4) 0.4473(3) 0.0712(15) Uani 1 1 d . . . . .
H24A H 0.5579 0.7533 0.4497 0.085 Uiso 1 1 calc R U . D 1
H24B H 0.6137 0.8311 0.3975 0.085 Uiso 1 1 calc R U . D 1
C8A C 0.5301(11) 0.7449(4) 1.2438(4) 0.032(2) Uani 0.520(14) 1 d . . P E 1
H8A1 H 0.4435 0.7353 1.2814 0.038 Uiso 0.520(14) 1 calc R U P E 1
H8A2 H 0.6026 0.7948 1.2579 0.038 Uiso 0.520(14) 1 calc R U P E 1
C9A C 0.6378(14) 0.6637(5) 1.2334(5) 0.036(2) Uani 0.520(14) 1 d . . P E 1
H9A H 0.7308 0.6764 1.1985 0.044 Uiso 0.520(14) 1 calc R U P E 1
C21A C 0.6703(11) 0.9081(6) 0.5389(4) 0.048(2) Uani 0.490(10) 1 d . . P F 1
H21A H 0.7117 0.9623 0.5149 0.058 Uiso 0.490(10) 1 calc R U P F 1
C23A C 0.4288(12) 0.8684(6) 0.4704(5) 0.048(2) Uani 0.490(10) 1 d . . P F 1
H23A H 0.3963 0.9116 0.4336 0.058 Uiso 0.490(10) 1 calc R U P F 1
H23B H 0.3303 0.8298 0.4799 0.058 Uiso 0.490(10) 1 calc R U P F 1
C8B C 0.6128(11) 0.7350(4) 1.2159(5) 0.027(2) Uani 0.480(14) 1 d . . P E 2
H8B1 H 0.7071 0.7246 1.1819 0.033 Uiso 0.480(14) 1 calc R U P E 2
H8B2 H 0.6478 0.7812 1.2496 0.033 Uiso 0.480(14) 1 calc R U P E 2
C9B C 0.5686(13) 0.6525(5) 1.2553(5) 0.0276(18) Uani 0.480(14) 1 d . . P E 2
H9B H 0.4647 0.6625 1.2850 0.033 Uiso 0.480(14) 1 calc R U P E 2
C21B C 0.6058(8) 0.8619(4) 0.5680(3) 0.0272(16) Uani 0.510(10) 1 d . . P F 2
H21B H 0.5448 0.8295 0.6066 0.033 Uiso 0.510(10) 1 calc R U P F 2
C23B C 0.516(2) 0.9042(11) 0.4530(5) 0.089(5) Uani 0.510(10) 1 d . . P F 2
H23C H 0.4076 0.9106 0.4262 0.106 Uiso 0.510(10) 1 calc R U P F 2
H23D H 0.5986 0.9481 0.4361 0.106 Uiso 0.510(10) 1 calc R U P F 2
H2 H 0.752(5) 1.015(3) 0.651(2) 0.041(11) Uiso 1 1 d . . . . .
N1 N 0.4487(5) 0.7617(2) 1.1759(2) 0.0554(11) Uani 1 1 d . . . . .
N2 N 0.7246(4) 0.9632(2) 0.65838(16) 0.0343(6) Uani 1 1 d . . . . .
O1 O 0.6088(3) 0.86960(15) 1.12962(13) 0.0373(5) Uani 1 1 d . . . . .
O2 O 0.5376(4) 0.58872(17) 1.20790(14) 0.0464(7) Uani 1 1 d . . . . .
O3 O 0.6411(3) 0.86073(14) 0.73709(13) 0.0341(5) Uani 1 1 d . . . . .
O4A O 0.7183(10) 0.8363(7) 0.4924(4) 0.064(3) Uani 0.490(10) 1 d . . P F 1
O4B O 0.6667(9) 0.7972(4) 0.5192(3) 0.0444(16) Uani 0.510(10) 1 d . . P F 2
S1 S 0.59642(10) 0.88718(5) 0.98374(4) 0.0320(2) Uani 1 1 d . . . . .
S2 S 0.59972(10) 0.87763(5) 0.87497(4) 0.03134(19) Uani 1 1 d . . . . .
H1 H 0.363(7) 0.733(3) 1.177(3) 0.070(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.391(5) . ?
C1 C4 1.395(4) . ?
C1 C7 1.495(4) . ?
C2 C6 1.391(4) . ?
C2 C4 1.392(4) . ?
C3 C6 1.374(5) . ?
C3 C5 1.383(5) . ?
C4 S1 1.789(3) . ?
C7 O1 1.240(4) . ?
C7 N1 1.331(5) . ?
C10 C11 1.522(5) . ?
C10 C9B 1.526(8) . ?
C10 C9A 1.556(9) . ?
C11 C12 1.510(5) . ?
C12 O2 1.432(4) . ?
C13 C14 1.386(4) . ?
C13 C18 1.403(4) . ?
C13 S2 1.793(3) . ?
C14 C15 1.375(5) . ?
C15 C16 1.379(5) . ?
C16 C17 1.379(5) . ?
C17 C18 1.401(4) . ?
C18 C19 1.493(4) . ?
C19 O3 1.238(4) . ?
C19 N2 1.342(4) . ?
C20 C21A 1.429(9) . ?
C20 N2 1.462(5) . ?
C20 C21B 1.547(7) . ?
C22 C21B 1.354(8) . ?
C22 C21A 1.448(11) . ?
C22 C23A 1.451(10) . ?
C22 C23B 1.561(12) . ?
C24 O4A 1.390(9) . ?
C24 C23B 1.454(14) . ?
C24 C23A 1.516(12) . ?
C24 O4B 1.529(8) . ?
C8A N1 1.450(7) . ?
C8A C9A 1.519(13) . ?
C9A O2 1.474(9) . ?
C21A O4A 1.456(11) . ?
C8B C9B 1.507(12) . ?
C8B N1 1.545(7) . ?
C9B O2 1.345(8) . ?
C21B O4B 1.434(8) . ?
S1 S2 2.0469(11) . ?

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
C5 C1 C4 119.2(3) . . ?
C5 C1 C7 120.1(3) . . ?
C4 C1 C7 120.7(3) . . ?
C6 C2 C4 120.6(3) . . ?
C6 C3 C5 119.3(3) . . ?
C2 C4 C1 119.2(3) . . ?
C2 C4 S1 121.7(2) . . ?
C1 C4 S1 119.1(2) . . ?
C3 C5 C1 121.4(3) . . ?
C3 C6 C2 120.3(3) . . ?
O1 C7 N1 122.3(3) . . ?
O1 C7 C1 121.4(3) . . ?
N1 C7 C1 116.4(3) . . ?
C11 C10 C9B 97.4(4) . . ?
C11 C10 C9A 108.3(4) . . ?
C12 C11 C10 103.5(3) . . ?
O2 C12 C11 106.3(3) . . ?
C14 C13 C18 119.1(3) . . ?
C14 C13 S2 121.1(3) . . ?
C18 C13 S2 119.7(2) . . ?
C15 C14 C13 121.6(3) . . ?
C14 C15 C16 120.0(3) . . ?
C15 C16 C17 119.4(3) . . ?
C16 C17 C18 121.6(3) . . ?
C17 C18 C13 118.4(3) . . ?
C17 C18 C19 121.0(3) . . ?
C13 C18 C19 120.5(3) . . ?
O3 C19 N2 121.8(3) . . ?
O3 C19 C18 120.0(3) . . ?
N2 C19 C18 118.1(3) . . ?
C21A C20 N2 114.7(4) . . ?
N2 C20 C21B 111.2(3) . . ?
C21A C22 C23A 109.6(6) . . ?
C21B C22 C23B 108.0(6) . . ?
O4A C24 C23A 108.6(5) . . ?
C23B C24 O4B 105.6(6) . . ?
N1 C8A C9A 106.1(7) . . ?
O2 C9A C8A 112.7(7) . . ?
O2 C9A C10 102.2(6) . . ?
C8A C9A C10 114.1(7) . . ?
C20 C21A C22 125.4(7) . . ?
C20 C21A O4A 107.5(7) . . ?
C22 C21A O4A 104.6(7) . . ?
C22 C23A C24 103.3(6) . . ?
C9B C8B N1 105.7(6) . . ?
O2 C9B C8B 109.2(8) . . ?
O2 C9B C10 110.3(5) . . ?
C8B C9B C10 109.0(7) . . ?
C22 C21B O4B 109.0(5) . . ?
C22 C21B C20 123.5(5) . . ?
O4B C21B C20 105.0(5) . . ?
C24 C23B C22 101.0(8) . . ?
C7 N1 C8A 129.6(4) . . ?
C7 N1 C8B 112.3(4) . . ?
C19 N2 C20 122.0(3) . . ?
C9B O2 C12 108.5(4) . . ?
C12 O2 C9A 109.8(4) . . ?
C24 O4A C21A 109.6(6) . . ?
C21B O4B C24 106.7(5) . . ?
C4 S1 S2 104.22(11) . . ?
C13 S2 S1 104.76(11) . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.050


####################################################################### 
# 
# 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_compound2e
_database_code_depnum_ccdc_archive 'CCDC 2193292'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 N2 O4 S2'
_chemical_formula_weight         516.61

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.532(2)
_cell_length_b                   10.4494(19)
_cell_length_c                   20.496(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.173(12)
_cell_angle_gamma                90.00
_cell_volume                     2450.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3199
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      25.77

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_procecompound2e_details ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14783
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3032
_reflns_number_gt                2335
_reflns_threshold_exprecompound2eion >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodnecompound2e of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold exprecompound2eion of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3030
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1798
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodnecompound2e_of_fit_ref 1.164
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_acompound2eembly
_atom_site_disorder_group
S1 S 0.48938(5) 0.04362(6) 0.29898(3) 0.0326(2) Uani 1 1 d . . .
C1 C 0.63767(19) -0.0606(2) 0.40216(11) 0.0251(5) Uani 1 1 d . . .
C2 C 0.59490(19) -0.0704(2) 0.33506(11) 0.0267(5) Uani 1 1 d . . .
C7 C 0.5927(2) 0.0429(2) 0.44235(11) 0.0276(5) Uani 1 1 d . . .
C8 C 0.6462(2) 0.1831(2) 0.53933(11) 0.0293(5) Uani 1 1 d . . .
C3 C 0.7210(2) -0.1479(2) 0.42913(11) 0.0297(5) Uani 1 1 d . . .
H3 H 0.7499 -0.1415 0.4734 0.036 Uiso 1 1 calc R . .
C9 C 0.7218(2) 0.1873(3) 0.59829(11) 0.0303(5) Uani 1 1 d . . .
C4 C 0.6375(2) -0.1664(2) 0.29736(11) 0.0304(5) Uani 1 1 d . . .
H4 H 0.6106 -0.1727 0.2528 0.037 Uiso 1 1 calc R . .
C5 C 0.7620(2) -0.2442(2) 0.39181(12) 0.0332(6) Uani 1 1 d . . .
H5 H 0.8172 -0.3025 0.4108 0.040 Uiso 1 1 calc R . .
C6 C 0.7197(2) -0.2524(3) 0.32597(12) 0.0346(6) Uani 1 1 d . . .
H6 H 0.7468 -0.3168 0.3004 0.041 Uiso 1 1 calc R . .
C10 C 0.5537(2) 0.3760(3) 0.57152(13) 0.0380(6) Uani 1 1 d . . .
H10 H 0.4969 0.4390 0.5629 0.046 Uiso 1 1 calc R . .
C11 C 0.7145(2) 0.2861(3) 0.64228(11) 0.0334(6) Uani 1 1 d . . .
H11 H 0.7663 0.2897 0.6808 0.040 Uiso 1 1 calc R . .
C12 C 0.5619(2) 0.2778(3) 0.52630(12) 0.0346(6) Uani 1 1 d . . .
H12 H 0.5109 0.2756 0.4874 0.042 Uiso 1 1 calc R . .
C13 C 0.6300(2) 0.3798(3) 0.62907(12) 0.0371(6) Uani 1 1 d . . .
H13 H 0.6245 0.4456 0.6591 0.045 Uiso 1 1 calc R . .
C14 C 0.8779(3) 0.0880(3) 0.66703(13) 0.0494(8) Uani 1 1 d . . .
H14A H 0.8329 0.0966 0.7031 0.074 Uiso 1 1 calc R . .
H14B H 0.9324 0.1576 0.6677 0.074 Uiso 1 1 calc R . .
H14C H 0.9199 0.0084 0.6709 0.074 Uiso 1 1 calc R . .
O1 O 0.49550(16) 0.08932(19) 0.42656(9) 0.0412(5) Uani 1 1 d . . .
O2 O 0.80185(16) 0.08983(18) 0.60677(8) 0.0369(5) Uani 1 1 d . . .
N1 N 0.66584(17) 0.0840(2) 0.49520(9) 0.0288(5) Uani 1 1 d . . .
H1 H 0.7319 0.0452 0.5027 0.035 Uiso 1 1 calc R . .


_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 1.795(2) . ?
S1 S1 2.0530(13) 2_655 ?
C1 C3 1.389(3) . ?
C1 C2 1.406(3) . ?
C1 C7 1.491(3) . ?
C2 C4 1.393(3) . ?
C7 O1 1.227(3) . ?
C7 N1 1.357(3) . ?
C8 C12 1.389(3) . ?
C8 C9 1.400(3) . ?
C8 N1 1.411(3) . ?
C3 C5 1.383(3) . ?
C9 O2 1.371(3) . ?
C9 C11 1.380(3) . ?
C4 C6 1.382(3) . ?
C5 C6 1.379(3) . ?
C10 C13 1.381(4) . ?
C10 C12 1.394(4) . ?
C11 C13 1.384(4) . ?
C14 O2 1.423(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 S1 104.20(8) . 2_655 ?
C3 C1 C2 118.9(2) . . ?
C3 C1 C7 121.8(2) . . ?
C2 C1 C7 119.3(2) . . ?
C4 C2 C1 119.3(2) . . ?
C4 C2 S1 121.17(17) . . ?
C1 C2 S1 119.48(18) . . ?
O1 C7 N1 122.8(2) . . ?
O1 C7 C1 120.7(2) . . ?
N1 C7 C1 116.5(2) . . ?
C12 C8 C9 119.3(2) . . ?
C12 C8 N1 124.3(2) . . ?
C9 C8 N1 116.3(2) . . ?
C5 C3 C1 121.7(2) . . ?
O2 C9 C11 124.6(2) . . ?
O2 C9 C8 115.0(2) . . ?
C11 C9 C8 120.3(2) . . ?
C6 C4 C2 120.2(2) . . ?
C6 C5 C3 118.9(2) . . ?
C5 C6 C4 121.0(2) . . ?
C13 C10 C12 120.0(2) . . ?
C9 C11 C13 120.0(2) . . ?
C8 C12 C10 120.0(2) . . ?
C10 C13 C11 120.3(2) . . ?
C9 O2 C14 116.9(2) . . ?
C7 N1 C8 127.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_compound2c
_database_code_depnum_ccdc_archive 'CCDC 2193291'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            C22H28N2O2S2
_chemical_formula_weight         416.58

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2697(11)
_cell_length_b                   13.9696(13)
_cell_length_c                   15.8362(14)
_cell_angle_alpha                113.646(6)
_cell_angle_beta                 92.993(6)
_cell_angle_gamma                100.554(6)
_cell_volume                     2223.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3639
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      24.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25532
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.418
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             10716
_reflns_number_gt                6769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0778P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10716
_refine_ls_number_parameters     517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.13331(5) 0.57931(4) 0.90479(4) 0.03145(15) Uani 1 1 d . . . . .
S2 S 0.07208(6) 0.41889(4) 0.82639(4) 0.03014(15) Uani 1 1 d . . . . .
S3 S 0.31909(5) 0.42499(4) 0.56491(4) 0.03013(15) Uani 1 1 d . . . . .
S4 S 0.39332(6) 0.57973(4) 0.65494(4) 0.03350(16) Uani 1 1 d . . . . .
O2 O 0.04306(14) 0.19500(12) 0.71510(11) 0.0298(4) Uani 1 1 d . . . . .
O1 O 0.23754(14) 0.78169(12) 1.04155(11) 0.0322(4) Uani 1 1 d . . . . .
O3 O 0.21486(14) 0.21153(13) 0.43029(10) 0.0333(4) Uani 1 1 d . . . . .
O4 O 0.46723(14) 0.80158(12) 0.78177(11) 0.0318(4) Uani 1 1 d . . . . .
N1 N 0.16535(16) 0.79436(14) 1.17580(12) 0.0272(4) Uani 1 1 d . . . . .
H1 H 0.1004 0.7940 1.2020 0.033 Uiso 1 1 calc R U . . .
N2 N 0.17347(17) 0.18394(14) 0.60826(13) 0.0268(4) Uani 1 1 d . . . . .
H2 H 0.1970 0.2075 0.5680 0.032 Uiso 1 1 calc R U . . .
N3 N 0.30728(16) 0.21046(13) 0.30539(12) 0.0244(4) Uani 1 1 d . . . . .
H3 H 0.3766 0.2153 0.2853 0.029 Uiso 1 1 calc R U . . .
N4 N 0.32734(16) 0.82156(13) 0.88302(12) 0.0247(4) Uani 1 1 d . . . . .
H4 H 0.2976 0.7994 0.9226 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2531(3) 0.8360(3) 1.33131(18) 0.0698(11) Uani 1 1 d . . . . .
H5 H 0.2043 0.7701 1.3277 0.105 Uiso 1 1 calc R U . . .
H6 H 0.2087 0.8917 1.3541 0.105 Uiso 1 1 calc R U . . .
H7 H 0.3272 0.8554 1.3729 0.105 Uiso 1 1 calc R U . . .
C8 C 0.2831(2) 0.82166(17) 1.23532(15) 0.0286(5) Uani 1 1 d . . . . .
C7 C 0.1515(2) 0.77032(16) 1.08487(15) 0.0254(5) Uani 1 1 d . . . . .
C6 C 0.02406(19) 0.72112(16) 1.03439(14) 0.0240(5) Uani 1 1 d . . . . .
C1 C 0.0040(2) 0.62735(17) 0.95102(15) 0.0262(5) Uani 1 1 d . . . . .
C12 C 0.0354(2) 0.40503(17) 0.71045(15) 0.0265(5) Uani 1 1 d . . . . .
C13 C 0.04230(19) 0.30844(16) 0.63608(15) 0.0254(5) Uani 1 1 d . . . . .
C18 C 0.0856(2) 0.22312(16) 0.65606(15) 0.0250(5) Uani 1 1 d . . . . .
C19 C 0.2328(2) 0.10298(17) 0.61987(16) 0.0283(5) Uani 1 1 d . . . . .
C20 C 0.1416(2) -0.00406(18) 0.58572(18) 0.0388(6) Uani 1 1 d . . . . .
H8 H 0.1113 -0.0273 0.5212 0.058 Uiso 1 1 calc R U . . .
H9 H 0.0750 0.0039 0.6215 0.058 Uiso 1 1 calc R U . . .
H10 H 0.1809 -0.0563 0.5929 0.058 Uiso 1 1 calc R U . . .
C21 C 0.2858(2) 0.1410(2) 0.72145(17) 0.0382(6) Uani 1 1 d . . . . .
H11 H 0.2208 0.1449 0.7587 0.057 Uiso 1 1 calc R U . . .
H12 H 0.3389 0.2106 0.7426 0.057 Uiso 1 1 calc R U . . .
H13 H 0.3310 0.0914 0.7270 0.057 Uiso 1 1 calc R U . . .
C2 C -0.1150(2) 0.57594(19) 0.90886(16) 0.0335(5) Uani 1 1 d . . . . .
H14 H -0.1295 0.5126 0.8549 0.040 Uiso 1 1 calc R U . . .
C3 C -0.2120(2) 0.6177(2) 0.94610(17) 0.0367(6) Uani 1 1 d . . . . .
H15 H -0.2912 0.5824 0.9171 0.044 Uiso 1 1 calc R U . . .
C4 C -0.1919(2) 0.7116(2) 1.02618(17) 0.0358(6) Uani 1 1 d . . . . .
H16 H -0.2574 0.7403 1.0502 0.043 Uiso 1 1 calc R U . . .
C5 C -0.0747(2) 0.76289(18) 1.07061(15) 0.0294(5) Uani 1 1 d . . . . .
H17 H -0.0615 0.8256 1.1250 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3474(3) 0.7298(2) 1.19748(19) 0.0478(7) Uani 1 1 d . . . . .
H18 H 0.3687 0.7218 1.1375 0.072 Uiso 1 1 calc R U . . .
H19 H 0.2942 0.6647 1.1917 0.072 Uiso 1 1 calc R U . . .
H20 H 0.4200 0.7447 1.2393 0.072 Uiso 1 1 calc R U . . .
C9 C 0.3628(2) 0.9245(2) 1.2406(2) 0.0538(8) Uani 1 1 d . . . . .
H21 H 0.3239 0.9829 1.2698 0.081 Uiso 1 1 calc R U . . .
H22 H 0.3747 0.9172 1.1790 0.081 Uiso 1 1 calc R U . . .
H23 H 0.4403 0.9384 1.2766 0.081 Uiso 1 1 calc R U . . .
C14 C -0.0015(2) 0.48439(18) 0.69046(17) 0.0333(5) Uani 1 1 d . . . . .
H24 H -0.0027 0.5498 0.7387 0.040 Uiso 1 1 calc R U . . .
C15 C -0.0364(2) 0.46668(19) 0.59922(17) 0.0360(6) Uani 1 1 d . . . . .
H25 H -0.0616 0.5201 0.5868 0.043 Uiso 1 1 calc R U . . .
C16 C -0.0341(2) 0.37031(19) 0.52654(17) 0.0326(5) Uani 1 1 d . . . . .
H26 H -0.0602 0.3579 0.4656 0.039 Uiso 1 1 calc R U . . .
C17 C 0.0072(2) 0.29237(18) 0.54501(16) 0.0282(5) Uani 1 1 d . . . . .
H27 H 0.0115 0.2285 0.4960 0.034 Uiso 1 1 calc R U . . .
C22 C 0.3371(2) 0.0933(2) 0.56108(19) 0.0422(6) Uani 1 1 d . . . . .
H28 H 0.3941 0.1613 0.5836 0.063 Uiso 1 1 calc R U . . .
H29 H 0.3050 0.0723 0.4973 0.063 Uiso 1 1 calc R U . . .
H30 H 0.3777 0.0404 0.5654 0.063 Uiso 1 1 calc R U . . .
C30 C 0.1180(2) 0.07643(19) 0.22032(19) 0.0422(6) Uani 1 1 d . . . . .
H31 H 0.0938 0.0768 0.2777 0.063 Uiso 1 1 calc R U . . .
H32 H 0.1633 0.0220 0.1944 0.063 Uiso 1 1 calc R U . . .
H33 H 0.0469 0.0618 0.1772 0.063 Uiso 1 1 calc R U . . .
C31 C 0.1972(2) 0.18503(17) 0.23883(15) 0.0280(5) Uani 1 1 d . . . . .
C29 C 0.3074(2) 0.22655(16) 0.39430(14) 0.0236(5) Uani 1 1 d . . . . .
C23 C 0.4297(2) 0.26974(17) 0.45343(14) 0.0246(5) Uani 1 1 d . . . . .
C24 C 0.4461(2) 0.36412(17) 0.53555(15) 0.0274(5) Uani 1 1 d . . . . .
C34 C 0.4085(2) 0.57596(17) 0.76689(15) 0.0267(5) Uani 1 1 d . . . . .
C35 C 0.42275(19) 0.67312(16) 0.84651(15) 0.0239(5) Uani 1 1 d . . . . .
C40 C 0.40926(19) 0.77229(16) 0.83473(14) 0.0244(5) Uani 1 1 d . . . . .
C41 C 0.2839(2) 0.91115(18) 0.87372(15) 0.0278(5) Uani 1 1 d . . . . .
C42 C 0.2349(3) 0.8788(2) 0.77195(17) 0.0436(6) Uani 1 1 d . . . . .
H34 H 0.1748 0.8126 0.7493 0.065 Uiso 1 1 calc R U . . .
H35 H 0.3006 0.8698 0.7353 0.065 Uiso 1 1 calc R U . . .
H36 H 0.1984 0.9338 0.7673 0.065 Uiso 1 1 calc R U . . .
C32 C 0.2430(3) 0.1839(2) 0.14909(17) 0.0501(7) Uani 1 1 d . . . . .
H37 H 0.2889 0.1294 0.1257 0.075 Uiso 1 1 calc R U . . .
H38 H 0.2941 0.2525 0.1619 0.075 Uiso 1 1 calc R U . . .
H39 H 0.1746 0.1690 0.1034 0.075 Uiso 1 1 calc R U . . .
C36 C 0.4407(2) 0.67371(17) 0.93411(15) 0.0274(5) Uani 1 1 d . . . . .
H40 H 0.4528 0.7381 0.9868 0.033 Uiso 1 1 calc R U . . .
C37 C 0.4409(2) 0.57942(19) 0.94394(16) 0.0332(5) Uani 1 1 d . . . . .
H41 H 0.4540 0.5806 1.0029 0.040 Uiso 1 1 calc R U . . .
C38 C 0.4217(2) 0.48411(19) 0.86585(17) 0.0350(6) Uani 1 1 d . . . . .
H42 H 0.4187 0.4205 0.8724 0.042 Uiso 1 1 calc R U . . .
C39 C 0.4067(2) 0.48167(18) 0.77789(16) 0.0324(5) Uani 1 1 d . . . . .
H43 H 0.3953 0.4168 0.7258 0.039 Uiso 1 1 calc R U . . .
C43 C 0.3851(2) 1.01182(18) 0.91067(19) 0.0417(6) Uani 1 1 d . . . . .
H44 H 0.4527 0.9981 0.8765 0.063 Uiso 1 1 calc R U . . .
H45 H 0.4111 1.0323 0.9754 0.063 Uiso 1 1 calc R U . . .
H46 H 0.3556 1.0687 0.9034 0.063 Uiso 1 1 calc R U . . .
C44 C 0.1800(2) 0.9294(2) 0.93257(17) 0.0378(6) Uani 1 1 d . . . . .
H47 H 0.2097 0.9456 0.9958 0.057 Uiso 1 1 calc R U . . .
H48 H 0.1159 0.8657 0.9084 0.057 Uiso 1 1 calc R U . . .
H49 H 0.1491 0.9881 0.9305 0.057 Uiso 1 1 calc R U . . .
C25 C 0.5596(2) 0.4049(2) 0.59044(17) 0.0382(6) Uani 1 1 d . . . . .
H50 H 0.5730 0.4685 0.6440 0.046 Uiso 1 1 calc R U . . .
C26 C 0.6523(2) 0.3512(2) 0.56555(18) 0.0440(7) Uani 1 1 d . . . . .
H51 H 0.7271 0.3782 0.6037 0.053 Uiso 1 1 calc R U . . .
C27 C 0.6362(2) 0.2580(2) 0.48505(18) 0.0401(6) Uani 1 1 d . . . . .
H52 H 0.6995 0.2227 0.4690 0.048 Uiso 1 1 calc R U . . .
C28 C 0.5251(2) 0.21797(18) 0.42879(16) 0.0304(5) Uani 1 1 d . . . . .
H53 H 0.5139 0.1560 0.3740 0.036 Uiso 1 1 calc R U . . .
C33 C 0.1267(2) 0.2733(2) 0.27626(19) 0.0437(7) Uani 1 1 d . . . . .
H54 H 0.1797 0.3414 0.2900 0.066 Uiso 1 1 calc R U . . .
H55 H 0.0966 0.2737 0.3320 0.066 Uiso 1 1 calc R U . . .
H56 H 0.0595 0.2603 0.2304 0.066 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 C1 1.785(2) . ?
S1 S2 2.0376(8) . ?
S2 C12 1.785(2) . ?
S3 C24 1.785(2) . ?
S3 S4 2.0362(8) . ?
S4 C34 1.795(2) . ?
O2 C18 1.237(2) . ?
O1 C7 1.240(2) . ?
O3 C29 1.239(2) . ?
O4 C40 1.238(2) . ?
N1 C7 1.334(3) . ?
N1 C8 1.480(3) . ?
N1 H1 0.8600 . ?
N2 C18 1.341(3) . ?
N2 C19 1.480(3) . ?
N2 H2 0.8600 . ?
N3 C29 1.334(3) . ?
N3 C31 1.475(3) . ?
N3 H3 0.8600 . ?
N4 C40 1.340(3) . ?
N4 C41 1.481(3) . ?
N4 H4 0.8600 . ?
C11 C8 1.516(3) . ?
C11 H5 0.9600 . ?
C11 H6 0.9600 . ?
C11 H7 0.9600 . ?
C8 C9 1.516(3) . ?
C8 C10 1.517(3) . ?
C7 C6 1.501(3) . ?
C6 C5 1.394(3) . ?
C6 C1 1.408(3) . ?
C1 C2 1.388(3) . ?
C12 C14 1.392(3) . ?
C12 C13 1.410(3) . ?
C13 C17 1.391(3) . ?
C13 C18 1.503(3) . ?
C19 C20 1.522(3) . ?
C19 C21 1.525(3) . ?
C19 C22 1.529(3) . ?
C20 H8 0.9600 . ?
C20 H9 0.9600 . ?
C20 H10 0.9600 . ?
C21 H11 0.9600 . ?
C21 H12 0.9600 . ?
C21 H13 0.9600 . ?
C2 C3 1.382(3) . ?
C2 H14 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H15 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H16 0.9300 . ?
C5 H17 0.9300 . ?
C10 H18 0.9600 . ?
C10 H19 0.9600 . ?
C10 H20 0.9600 . ?
C9 H21 0.9600 . ?
C9 H22 0.9600 . ?
C9 H23 0.9600 . ?
C14 C15 1.386(3) . ?
C14 H24 0.9300 . ?
C15 C16 1.382(3) . ?
C15 H25 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H26 0.9300 . ?
C17 H27 0.9300 . ?
C22 H28 0.9600 . ?
C22 H29 0.9600 . ?
C22 H30 0.9600 . ?
C30 C31 1.518(3) . ?
C30 H31 0.9600 . ?
C30 H32 0.9600 . ?
C30 H33 0.9600 . ?
C31 C33 1.524(3) . ?
C31 C32 1.532(3) . ?
C29 C23 1.499(3) . ?
C23 C28 1.391(3) . ?
C23 C24 1.405(3) . ?
C24 C25 1.392(3) . ?
C34 C39 1.393(3) . ?
C34 C35 1.409(3) . ?
C35 C36 1.388(3) . ?
C35 C40 1.503(3) . ?
C41 C43 1.518(3) . ?
C41 C44 1.529(3) . ?
C41 C42 1.529(3) . ?
C42 H34 0.9600 . ?
C42 H35 0.9600 . ?
C42 H36 0.9600 . ?
C32 H37 0.9600 . ?
C32 H38 0.9600 . ?
C32 H39 0.9600 . ?
C36 C37 1.387(3) . ?
C36 H40 0.9300 . ?
C37 C38 1.376(3) . ?
C37 H41 0.9300 . ?
C38 C39 1.380(3) . ?
C38 H42 0.9300 . ?
C39 H43 0.9300 . ?
C43 H44 0.9600 . ?
C43 H45 0.9600 . ?
C43 H46 0.9600 . ?
C44 H47 0.9600 . ?
C44 H48 0.9600 . ?
C44 H49 0.9600 . ?
C25 C26 1.379(3) . ?
C25 H50 0.9300 . ?
C26 C27 1.382(3) . ?
C26 H51 0.9300 . ?
C27 C28 1.379(3) . ?
C27 H52 0.9300 . ?
C28 H53 0.9300 . ?
C33 H54 0.9600 . ?
C33 H55 0.9600 . ?
C33 H56 0.9600 . ?

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
C1 S1 S2 105.90(8) . . ?
C12 S2 S1 105.38(7) . . ?
C24 S3 S4 104.94(7) . . ?
C34 S4 S3 104.26(8) . . ?
C7 N1 C8 125.44(18) . . ?
C7 N1 H1 117.3 . . ?
C8 N1 H1 117.3 . . ?
C18 N2 C19 124.64(18) . . ?
C18 N2 H2 117.7 . . ?
C19 N2 H2 117.7 . . ?
C29 N3 C31 124.97(18) . . ?
C29 N3 H3 117.5 . . ?
C31 N3 H3 117.5 . . ?
C40 N4 C41 125.19(18) . . ?
C40 N4 H4 117.4 . . ?
C41 N4 H4 117.4 . . ?
C8 C11 H5 109.5 . . ?
C8 C11 H6 109.5 . . ?
H5 C11 H6 109.5 . . ?
C8 C11 H7 109.5 . . ?
H5 C11 H7 109.5 . . ?
H6 C11 H7 109.5 . . ?
N1 C8 C9 110.9(2) . . ?
N1 C8 C11 106.49(19) . . ?
C9 C8 C11 109.9(2) . . ?
N1 C8 C10 109.56(18) . . ?
C9 C8 C10 110.6(2) . . ?
C11 C8 C10 109.2(2) . . ?
O1 C7 N1 123.6(2) . . ?
O1 C7 C6 120.3(2) . . ?
N1 C7 C6 116.03(18) . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C7 121.53(19) . . ?
C1 C6 C7 118.72(19) . . ?
C2 C1 C6 118.8(2) . . ?
C2 C1 S1 122.92(17) . . ?
C6 C1 S1 118.23(17) . . ?
C14 C12 C13 118.8(2) . . ?
C14 C12 S2 122.97(17) . . ?
C13 C12 S2 118.21(17) . . ?
C17 C13 C12 119.7(2) . . ?
C17 C13 C18 120.66(19) . . ?
C12 C13 C18 119.6(2) . . ?
O2 C18 N2 123.9(2) . . ?
O2 C18 C13 120.44(19) . . ?
N2 C18 C13 115.62(19) . . ?
N2 C19 C20 109.95(19) . . ?
N2 C19 C21 110.28(18) . . ?
C20 C19 C21 111.0(2) . . ?
N2 C19 C22 106.32(18) . . ?
C20 C19 C22 110.40(19) . . ?
C21 C19 C22 108.8(2) . . ?
C19 C20 H8 109.5 . . ?
C19 C20 H9 109.5 . . ?
H8 C20 H9 109.5 . . ?
C19 C20 H10 109.5 . . ?
H8 C20 H10 109.5 . . ?
H9 C20 H10 109.5 . . ?
C19 C21 H11 109.5 . . ?
C19 C21 H12 109.5 . . ?
H11 C21 H12 109.5 . . ?
C19 C21 H13 109.5 . . ?
H11 C21 H13 109.5 . . ?
H12 C21 H13 109.5 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H14 119.6 . . ?
C1 C2 H14 119.6 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H15 119.9 . . ?
C2 C3 H15 119.9 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H16 120.0 . . ?
C3 C4 H16 120.0 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H17 119.8 . . ?
C6 C5 H17 119.8 . . ?
C8 C10 H18 109.5 . . ?
C8 C10 H19 109.5 . . ?
H18 C10 H19 109.5 . . ?
C8 C10 H20 109.5 . . ?
H18 C10 H20 109.5 . . ?
H19 C10 H20 109.5 . . ?
C8 C9 H21 109.5 . . ?
C8 C9 H22 109.5 . . ?
H21 C9 H22 109.5 . . ?
C8 C9 H23 109.5 . . ?
H21 C9 H23 109.5 . . ?
H22 C9 H23 109.5 . . ?
C15 C14 C12 120.5(2) . . ?
C15 C14 H24 119.7 . . ?
C12 C14 H24 119.7 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H25 119.7 . . ?
C14 C15 H25 119.7 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H26 120.2 . . ?
C17 C16 H26 120.2 . . ?
C16 C17 C13 120.7(2) . . ?
C16 C17 H27 119.6 . . ?
C13 C17 H27 119.6 . . ?
C19 C22 H28 109.5 . . ?
C19 C22 H29 109.5 . . ?
H28 C22 H29 109.5 . . ?
C19 C22 H30 109.5 . . ?
H28 C22 H30 109.5 . . ?
H29 C22 H30 109.5 . . ?
C31 C30 H31 109.5 . . ?
C31 C30 H32 109.5 . . ?
H31 C30 H32 109.5 . . ?
C31 C30 H33 109.5 . . ?
H31 C30 H33 109.5 . . ?
H32 C30 H33 109.5 . . ?
N3 C31 C30 110.96(19) . . ?
N3 C31 C33 109.52(18) . . ?
C30 C31 C33 111.1(2) . . ?
N3 C31 C32 105.95(19) . . ?
C30 C31 C32 110.2(2) . . ?
C33 C31 C32 109.0(2) . . ?
O3 C29 N3 124.7(2) . . ?
O3 C29 C23 119.37(19) . . ?
N3 C29 C23 115.91(18) . . ?
C28 C23 C24 120.2(2) . . ?
C28 C23 C29 121.35(19) . . ?
C24 C23 C29 118.45(19) . . ?
C25 C24 C23 118.7(2) . . ?
C25 C24 S3 123.24(17) . . ?
C23 C24 S3 118.09(17) . . ?
C39 C34 C35 119.2(2) . . ?
C39 C34 S4 122.86(17) . . ?
C35 C34 S4 117.97(16) . . ?
C36 C35 C34 119.3(2) . . ?
C36 C35 C40 121.39(18) . . ?
C34 C35 C40 119.13(19) . . ?
O4 C40 N4 124.4(2) . . ?
O4 C40 C35 121.29(19) . . ?
N4 C40 C35 114.29(18) . . ?
N4 C41 C43 110.68(19) . . ?
N4 C41 C44 105.57(18) . . ?
C43 C41 C44 109.89(19) . . ?
N4 C41 C42 109.78(18) . . ?
C43 C41 C42 111.3(2) . . ?
C44 C41 C42 109.5(2) . . ?
C41 C42 H34 109.5 . . ?
C41 C42 H35 109.5 . . ?
H34 C42 H35 109.5 . . ?
C41 C42 H36 109.5 . . ?
H34 C42 H36 109.5 . . ?
H35 C42 H36 109.5 . . ?
C31 C32 H37 109.5 . . ?
C31 C32 H38 109.5 . . ?
H37 C32 H38 109.5 . . ?
C31 C32 H39 109.5 . . ?
H37 C32 H39 109.5 . . ?
H38 C32 H39 109.5 . . ?
C37 C36 C35 120.8(2) . . ?
C37 C36 H40 119.6 . . ?
C35 C36 H40 119.6 . . ?
C38 C37 C36 119.5(2) . . ?
C38 C37 H41 120.2 . . ?
C36 C37 H41 120.2 . . ?
C37 C38 C39 120.9(2) . . ?
C37 C38 H42 119.6 . . ?
C39 C38 H42 119.6 . . ?
C38 C39 C34 120.3(2) . . ?
C38 C39 H43 119.9 . . ?
C34 C39 H43 119.9 . . ?
C41 C43 H44 109.5 . . ?
C41 C43 H45 109.5 . . ?
H44 C43 H45 109.5 . . ?
C41 C43 H46 109.5 . . ?
H44 C43 H46 109.5 . . ?
H45 C43 H46 109.5 . . ?
C41 C44 H47 109.5 . . ?
C41 C44 H48 109.5 . . ?
H47 C44 H48 109.5 . . ?
C41 C44 H49 109.5 . . ?
H47 C44 H49 109.5 . . ?
H48 C44 H49 109.5 . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H50 119.9 . . ?
C24 C25 H50 119.9 . . ?
C25 C26 C27 121.3(2) . . ?
C25 C26 H51 119.4 . . ?
C27 C26 H51 119.4 . . ?
C28 C27 C26 119.2(2) . . ?
C28 C27 H52 120.4 . . ?
C26 C27 H52 120.4 . . ?
C27 C28 C23 120.4(2) . . ?
C27 C28 H53 119.8 . . ?
C23 C28 H53 119.8 . . ?
C31 C33 H54 109.5 . . ?
C31 C33 H55 109.5 . . ?
H54 C33 H55 109.5 . . ?
C31 C33 H56 109.5 . . ?
H54 C33 H56 109.5 . . ?
H55 C33 H56 109.5 . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.057


####################################################################### 
# 
# 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_compound2o
_database_code_depnum_ccdc_archive 'CCDC 2193297'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N4 O2 S2'
_chemical_formula_weight         486.59

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   20.9157(11)
_cell_length_b                   4.9145(3)
_cell_length_c                   23.0352(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2367.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4698
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.257
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25741
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.768
_diffrn_reflns_theta_max         28.718
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             5762
_reflns_number_gt                4530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_max     0.876
_reflns_Friedel_fraction_full    0.890

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5762
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1554
_refine_ls_wR_factor_gt          0.1421
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.32043(5) -0.1543(2) 0.38650(6) 0.0287(3) Uani 1 1 d . . . . .
S2 S 0.41228(5) -0.1248(2) 0.41508(6) 0.0282(3) Uani 1 1 d . . . . .
C7 C 0.2025(2) 0.1369(9) 0.3425(2) 0.0234(9) Uani 1 1 d . . . . .
C1 C 0.2793(2) 0.1061(9) 0.4259(2) 0.0240(9) Uani 1 1 d . . . . .
C2 C 0.2246(2) 0.2223(8) 0.40163(19) 0.0204(9) Uani 1 1 d . . . . .
C3 C 0.1909(2) 0.4220(9) 0.4323(2) 0.0264(10) Uani 1 1 d . . . . .
H3 H 0.154168 0.503910 0.415378 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2994(2) 0.1924(11) 0.4811(2) 0.0320(11) Uani 1 1 d . . . . .
H4 H 0.336573 0.115857 0.498307 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2283(2) 0.2596(10) 0.2059(2) 0.0269(10) Uani 1 1 d . . . . .
C8 C 0.1712(2) 0.2900(11) 0.2457(2) 0.0298(10) Uani 1 1 d . . . . .
H8A H 0.144505 0.443772 0.232181 0.036 Uiso 1 1 calc R U . . .
H8B H 0.144974 0.122580 0.243924 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2105(2) 0.5002(11) 0.4867(2) 0.0322(11) Uani 1 1 d . . . . .
H5 H 0.186502 0.630740 0.507916 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2889(3) 0.3874(13) 0.1223(3) 0.0448(14) Uani 1 1 d . . . . .
H10 H 0.292618 0.500589 0.089059 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2352(3) 0.4229(12) 0.1574(3) 0.0386(12) Uani 1 1 d . . . . .
H11 H 0.204053 0.556625 0.148181 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2648(3) 0.3897(10) 0.5104(2) 0.0336(11) Uani 1 1 d . . . . .
H6 H 0.278868 0.449403 0.547493 0.040 Uiso 1 1 calc R U . . .
C12 C 0.3268(3) 0.0515(14) 0.1777(3) 0.0455(15) Uani 1 1 d . . . . .
H12 H 0.358623 -0.082090 0.185140 0.055 Uiso 1 1 calc R U . . .
C13 C 0.2757(3) 0.0667(12) 0.2157(3) 0.0401(13) Uani 1 1 d . . . . .
H13 H 0.273104 -0.052928 0.247978 0.048 Uiso 1 1 calc R U . . .
C14 C 0.4487(2) 0.1245(9) 0.3688(2) 0.0260(10) Uani 1 1 d . . . . .
C20 C 0.5292(2) 0.2058(9) 0.4474(2) 0.0236(9) Uani 1 1 d . . . . .
C15 C 0.5039(2) 0.2581(8) 0.3886(2) 0.0233(9) Uani 1 1 d . . . . .
C21 C 0.5146(2) 0.3468(10) 0.5791(2) 0.0290(10) Uani 1 1 d . . . . .
C22 C 0.4671(3) 0.1173(13) 0.6593(3) 0.0425(13) Uani 1 1 d . . . . .
H22 H 0.470055 -0.020619 0.688094 0.051 Uiso 1 1 calc R U . . .
C23 C 0.5173(3) 0.1466(11) 0.6210(3) 0.0383(13) Uani 1 1 d . . . . .
H23 H 0.553371 0.029799 0.623385 0.046 Uiso 1 1 calc R U . . .
C16 C 0.4548(3) 0.3761(12) 0.2792(3) 0.0459(15) Uani 1 1 d . . . . .
H16 H 0.437750 0.416125 0.241927 0.055 Uiso 1 1 calc R U . . .
C17 C 0.5340(2) 0.4471(11) 0.3524(2) 0.0348(12) Uani 1 1 d . . . . .
H17 H 0.571584 0.537678 0.365319 0.042 Uiso 1 1 calc R U . . .
C18 C 0.4247(3) 0.1896(11) 0.3150(3) 0.0366(12) Uani 1 1 d . . . . .
H18 H 0.386519 0.104415 0.302053 0.044 Uiso 1 1 calc R U . . .
C24 C 0.5692(2) 0.3940(10) 0.5379(2) 0.0300(11) Uani 1 1 d . . . . .
H24A H 0.592401 0.560722 0.549637 0.036 Uiso 1 1 calc R U . . .
H24B H 0.599400 0.239327 0.540556 0.036 Uiso 1 1 calc R U . . .
C25 C 0.4127(3) 0.4613(12) 0.6176(3) 0.0425(13) Uani 1 1 d . . . . .
H25 H 0.375721 0.573040 0.615970 0.051 Uiso 1 1 calc R U . . .
C26 C 0.4602(2) 0.5084(12) 0.5778(3) 0.0372(12) Uani 1 1 d . . . . .
H26 H 0.455965 0.649142 0.549775 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5095(3) 0.5027(12) 0.2981(3) 0.0435(14) Uani 1 1 d . . . . .
H19 H 0.530646 0.629461 0.273590 0.052 Uiso 1 1 calc R U . . .
O1 O 0.19604(17) -0.1054(7) 0.32952(17) 0.0335(8) Uani 1 1 d . . . . .
O2 O 0.53179(16) -0.0269(7) 0.46821(16) 0.0321(8) Uani 1 1 d . . . . .
N1 N 0.19094(19) 0.3388(8) 0.30577(18) 0.0259(9) Uani 1 1 d . . . . .
H1 H 0.195246 0.507581 0.317902 0.031 Uiso 1 1 calc R U . . .
N3 N 0.54824(19) 0.4230(8) 0.47780(19) 0.0282(9) Uani 1 1 d . . . . .
H3A H 0.548132 0.584790 0.461431 0.034 Uiso 1 1 calc R U . . .
N2 N 0.3346(2) 0.2114(10) 0.1315(2) 0.0363(10) Uani 1 1 d . . . . .
N4 N 0.4149(2) 0.2703(10) 0.6584(2) 0.0404(11) 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
S1 C1 1.790(5) . ?
S1 S2 2.0358(15) . ?
S2 C14 1.793(5) . ?
C7 O1 1.235(6) . ?
C7 N1 1.327(6) . ?
C7 C2 1.498(7) . ?
C1 C2 1.395(6) . ?
C1 C4 1.405(7) . ?
C2 C3 1.400(6) . ?
C3 C5 1.374(7) . ?
C4 C6 1.385(7) . ?
C9 C11 1.384(8) . ?
C9 C13 1.391(7) . ?
C9 C8 1.511(7) . ?
C8 N1 1.464(7) . ?
C5 C6 1.372(7) . ?
C10 N2 1.305(8) . ?
C10 C11 1.395(8) . ?
C12 N2 1.334(8) . ?
C12 C13 1.382(8) . ?
C14 C18 1.375(8) . ?
C14 C15 1.405(6) . ?
C20 O2 1.241(5) . ?
C20 N3 1.338(6) . ?
C20 C15 1.474(7) . ?
C15 C17 1.398(7) . ?
C21 C23 1.379(8) . ?
C21 C26 1.387(7) . ?
C21 C24 1.504(7) . ?
C22 N4 1.325(8) . ?
C22 C23 1.380(8) . ?
C16 C19 1.374(9) . ?
C16 C18 1.384(8) . ?
C17 C19 1.380(9) . ?
C24 N3 1.458(7) . ?
C25 N4 1.328(8) . ?
C25 C26 1.373(8) . ?

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
C1 S1 S2 103.82(16) . . ?
C14 S2 S1 104.91(17) . . ?
O1 C7 N1 123.1(5) . . ?
O1 C7 C2 121.7(4) . . ?
N1 C7 C2 115.3(4) . . ?
C2 C1 C4 119.0(4) . . ?
C2 C1 S1 118.9(3) . . ?
C4 C1 S1 122.1(4) . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 C7 120.2(4) . . ?
C3 C2 C7 120.0(4) . . ?
C5 C3 C2 120.4(4) . . ?
C6 C4 C1 119.7(5) . . ?
C11 C9 C13 116.8(5) . . ?
C11 C9 C8 121.0(5) . . ?
C13 C9 C8 122.2(5) . . ?
N1 C8 C9 111.5(4) . . ?
C6 C5 C3 120.0(5) . . ?
N2 C10 C11 125.3(6) . . ?
C9 C11 C10 118.7(5) . . ?
C5 C6 C4 121.1(5) . . ?
N2 C12 C13 124.5(5) . . ?
C12 C13 C9 119.1(5) . . ?
C18 C14 C15 118.9(5) . . ?
C18 C14 S2 122.7(4) . . ?
C15 C14 S2 118.4(4) . . ?
O2 C20 N3 121.2(5) . . ?
O2 C20 C15 122.1(4) . . ?
N3 C20 C15 116.6(4) . . ?
C17 C15 C14 119.2(5) . . ?
C17 C15 C20 120.1(4) . . ?
C14 C15 C20 120.7(4) . . ?
C23 C21 C26 117.2(5) . . ?
C23 C21 C24 121.4(4) . . ?
C26 C21 C24 121.4(5) . . ?
N4 C22 C23 123.8(6) . . ?
C21 C23 C22 119.4(5) . . ?
C19 C16 C18 119.3(6) . . ?
C19 C17 C15 120.3(5) . . ?
C14 C18 C16 121.7(6) . . ?
N3 C24 C21 112.7(4) . . ?
N4 C25 C26 124.6(5) . . ?
C25 C26 C21 118.8(5) . . ?
C16 C19 C17 120.5(5) . . ?
C7 N1 C8 122.2(4) . . ?
C20 N3 C24 120.6(4) . . ?
C10 N2 C12 115.5(5) . . ?
C22 N4 C25 116.2(5) . . ?

_refine_diff_density_max         1.210
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.088


####################################################################### 
# 
# 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_compound2p
_database_code_depnum_ccdc_archive 'CCDC 2193298'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O2 S2'
_chemical_formula_weight         384.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   9.0934(7)
_cell_length_b                   11.9605(10)
_cell_length_c                   17.7211(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.805(5)
_cell_angle_gamma                90
_cell_volume                     1917.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5711
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      24.12

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.294
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23980
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.703
_diffrn_reflns_theta_max         28.856
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.905
_reflns_number_total             8693
_reflns_number_gt                6800
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.735
_reflns_Friedel_fraction_full    0.811

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2194 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8693
_refine_ls_number_parameters     469
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.77700(12) 0.48564(11) 0.83277(7) 0.0301(3) Uani 1 1 d . . . . .
S2 S 0.77373(12) 0.53809(10) 0.72214(7) 0.0296(3) Uani 1 1 d . . . . .
S4 S 0.25070(12) 0.97808(11) 0.69060(7) 0.0306(3) Uani 1 1 d . . . . .
S3 S 0.24913(13) 0.98663(11) 0.80537(7) 0.0320(3) Uani 1 1 d . . . . .
C17 C 0.9199(5) 0.5937(4) 0.5770(3) 0.0262(10) Uani 1 1 d . . . . .
C16 C 0.9130(5) 0.4554(4) 0.6838(3) 0.0275(10) Uani 1 1 d . . . . .
C11 C 0.9726(5) 0.4885(4) 0.6170(3) 0.0255(10) Uani 1 1 d . . . . .
C1 C 0.9460(5) 0.5449(4) 0.8778(3) 0.0275(10) Uani 1 1 d . . . . .
C2 C 1.1301(6) 0.5579(4) 0.9847(3) 0.0323(11) Uani 1 1 d . . . . .
H2 H 1.166736 0.535280 1.034478 0.039 Uiso 1 1 calc R U . . .
C12 C 1.0787(6) 0.2966(5) 0.6936(3) 0.0380(12) Uani 1 1 d . . . . .
H12 H 1.117122 0.232509 0.720474 0.046 Uiso 1 1 calc R U . . .
C13 C 1.0810(5) 0.4221(4) 0.5887(3) 0.0322(11) Uani 1 1 d . . . . .
H13 H 1.118593 0.442246 0.542533 0.039 Uiso 1 1 calc R U . . .
C7 C 0.9115(5) 0.4332(4) 0.9952(3) 0.0290(10) Uani 1 1 d . . . . .
C14 C 0.9669(6) 0.3587(5) 0.7216(3) 0.0348(11) Uani 1 1 d . . . . .
H14 H 0.926951 0.335360 0.766499 0.042 Uiso 1 1 calc R U . . .
C3 C 1.0275(6) 0.6208(5) 0.8394(3) 0.0376(12) Uani 1 1 d . . . . .
H3 H 0.993150 0.642904 0.789266 0.045 Uiso 1 1 calc R U . . .
C8 C 0.9101(6) 0.2896(5) 1.0925(3) 0.0394(13) Uani 1 1 d . . . . .
H8A H 0.983258 0.232272 1.111404 0.047 Uiso 1 1 calc R U . . .
H8B H 0.833254 0.251734 1.057979 0.047 Uiso 1 1 calc R U . . .
C4 C 0.9978(5) 0.5130(4) 0.9517(3) 0.0287(10) Uani 1 1 d . . . . .
C15 C 1.1342(6) 0.3273(4) 0.6271(3) 0.0351(12) Uani 1 1 d . . . . .
H15 H 1.208983 0.283577 0.607619 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8390(6) 0.3356(5) 1.1586(4) 0.0435(14) Uani 1 1 d . . . . .
H9 H 0.776605 0.286504 1.182928 0.052 Uiso 1 1 calc R U . . .
C18 C 0.9701(7) 0.7442(5) 0.4921(4) 0.0452(15) Uani 1 1 d . . . . .
H18A H 1.060188 0.790012 0.489967 0.054 Uiso 1 1 calc R U . . .
H18B H 0.901380 0.786982 0.521059 0.054 Uiso 1 1 calc R U . . .
C5 C 1.2092(6) 0.6340(4) 0.9471(3) 0.0381(12) Uani 1 1 d . . . . .
H5 H 1.297655 0.665502 0.971236 0.046 Uiso 1 1 calc R U . . .
C6 C 1.1590(7) 0.6643(5) 0.8742(4) 0.0449(14) Uani 1 1 d . . . . .
H6 H 1.214571 0.715298 0.847434 0.054 Uiso 1 1 calc R U . . .
C10 C 0.8547(7) 0.4365(6) 1.1858(4) 0.0507(15) Uani 1 1 d . . . . .
H10A H 0.916042 0.488669 1.163401 0.061 Uiso 1 1 calc R U . . .
H10B H 0.804883 0.458020 1.228155 0.061 Uiso 1 1 calc R U . . .
C19 C 0.8997(8) 0.7277(7) 0.4138(4) 0.061(2) Uani 1 1 d . . . . .
H19 H 0.859411 0.792210 0.388085 0.073 Uiso 1 1 calc R U . . .
C20 C 0.8876(10) 0.6341(9) 0.3770(5) 0.079(3) Uani 1 1 d . . . . .
H20A H 0.926091 0.567233 0.400223 0.095 Uiso 1 1 calc R U . . .
H20B H 0.840241 0.632240 0.326661 0.095 Uiso 1 1 calc R U . . .
C37 C 0.3223(5) 1.0267(4) 0.5294(3) 0.0270(10) Uani 1 1 d . . . . .
C21 C 0.4028(5) 0.9039(4) 0.8450(3) 0.0263(10) Uani 1 1 d . . . . .
C31 C 0.4040(5) 1.0959(4) 0.5895(3) 0.0256(9) Uani 1 1 d . . . . .
C22 C 0.4247(5) 0.8901(4) 0.9235(3) 0.0263(10) Uani 1 1 d . . . . .
C23 C 0.5397(5) 0.8209(4) 0.9548(3) 0.0296(10) Uani 1 1 d . . . . .
H23 H 0.555425 0.811615 1.008297 0.036 Uiso 1 1 calc R U . . .
C27 C 0.3231(5) 0.9427(4) 0.9750(3) 0.0292(10) Uani 1 1 d . . . . .
C32 C 0.4988(5) 1.1822(4) 0.5709(3) 0.0336(11) Uani 1 1 d . . . . .
H32 H 0.510829 1.196462 0.519191 0.040 Uiso 1 1 calc R U . . .
C24 C 0.6118(6) 0.7831(4) 0.8319(3) 0.0352(12) Uani 1 1 d . . . . .
H24 H 0.676083 0.747245 0.800421 0.042 Uiso 1 1 calc R U . . .
C29 C 0.3646(6) 1.0364(5) 1.1740(3) 0.0390(13) Uani 1 1 d . . . . .
H29 H 0.401418 0.969824 1.198238 0.047 Uiso 1 1 calc R U . . .
C38 C 0.3028(6) 0.9561(5) 0.3994(3) 0.0388(12) Uani 1 1 d . . . . .
H38A H 0.300786 1.005527 0.354498 0.047 Uiso 1 1 calc R U . . .
H38B H 0.199203 0.943542 0.409877 0.047 Uiso 1 1 calc R U . . .
C28 C 0.2868(6) 1.0279(5) 1.0961(3) 0.0375(12) Uani 1 1 d . . . . .
H28A H 0.196564 0.982032 1.097655 0.045 Uiso 1 1 calc R U . . .
H28B H 0.256188 1.103481 1.077985 0.045 Uiso 1 1 calc R U . . .
C33 C 0.3833(5) 1.0801(4) 0.6664(3) 0.0280(10) Uani 1 1 d . . . . .
C25 C 0.4996(5) 0.8526(4) 0.7998(3) 0.0313(10) Uani 1 1 d . . . . .
H25 H 0.489092 0.865186 0.746553 0.038 Uiso 1 1 calc R U . . .
C26 C 0.6297(6) 0.7663(4) 0.9091(3) 0.0351(12) Uani 1 1 d . . . . .
H26 H 0.704323 0.716951 0.930754 0.042 Uiso 1 1 calc R U . . .
C34 C 0.4633(6) 1.1441(5) 0.7216(3) 0.0368(12) Uani 1 1 d . . . . .
H34 H 0.453012 1.130775 0.773639 0.044 Uiso 1 1 calc R U . . .
C35 C 0.5746(6) 1.2464(5) 0.6265(3) 0.0398(13) Uani 1 1 d . . . . .
H35 H 0.638568 1.304179 0.612978 0.048 Uiso 1 1 calc R U . . .
C40 C 0.4994(7) 0.8073(5) 0.4069(4) 0.0479(15) Uani 1 1 d . . . . .
H40A H 0.562479 0.850030 0.441818 0.057 Uiso 1 1 calc R U . . .
H40B H 0.530356 0.735992 0.390870 0.057 Uiso 1 1 calc R U . . .
C36 C 0.5576(6) 1.2269(5) 0.7017(3) 0.0413(13) Uani 1 1 d . . . . .
H36 H 0.611085 1.270521 0.739996 0.050 Uiso 1 1 calc R U . . .
C30 C 0.3848(7) 1.1308(6) 1.2106(4) 0.0469(14) Uani 1 1 d . . . . .
H30A H 0.349031 1.198611 1.187631 0.056 Uiso 1 1 calc R U . . .
H30B H 0.435174 1.131650 1.260257 0.056 Uiso 1 1 calc R U . . .
C39 C 0.3677(7) 0.8471(5) 0.3804(4) 0.0494(15) Uani 1 1 d . . . . .
H39 H 0.309042 0.801003 0.345598 0.059 Uiso 1 1 calc R U . . .
O4 O 0.2014(4) 0.9829(3) 0.5412(2) 0.0332(8) Uani 1 1 d . . . . .
O2 O 0.7977(3) 0.6342(3) 0.5877(2) 0.0306(8) Uani 1 1 d . . . . .
O3 O 0.1892(4) 0.9504(4) 0.9537(2) 0.0394(9) Uani 1 1 d . . . . .
O1 O 0.7754(4) 0.4260(3) 0.9784(2) 0.0346(8) Uani 1 1 d . . . . .
N3 N 0.3814(5) 0.9773(4) 1.0426(3) 0.0328(10) Uani 1 1 d . . . . .
H3A H 0.476909 0.970035 1.055531 0.039 Uiso 1 1 calc R U . . .
N4 N 0.3802(5) 1.0143(4) 0.4643(3) 0.0334(9) Uani 1 1 d . . . . .
H4 H 0.468541 1.042184 0.459957 0.040 Uiso 1 1 calc R U . . .
N2 N 1.0101(4) 0.6424(4) 0.5327(3) 0.0332(10) Uani 1 1 d . . . . .
H2A H 1.096687 0.611786 0.528027 0.040 Uiso 1 1 calc R U . . .
N1 N 0.9844(5) 0.3724(4) 1.0487(2) 0.0340(10) Uani 1 1 d . . . . .
H1 H 1.080466 0.381816 1.058385 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 C1 1.803(5) . ?
S1 S2 2.0558(17) . ?
S2 C16 1.793(5) . ?
S4 C33 1.797(5) . ?
S4 S3 2.0380(18) . ?
S3 C21 1.796(5) . ?
C17 O2 1.244(6) . ?
C17 N2 1.325(6) . ?
C17 C11 1.499(7) . ?
C16 C14 1.400(7) . ?
C16 C11 1.408(7) . ?
C11 C13 1.397(6) . ?
C1 C3 1.392(7) . ?
C1 C4 1.399(7) . ?
C2 C5 1.374(7) . ?
C2 C4 1.391(7) . ?
C12 C15 1.378(8) . ?
C12 C14 1.390(7) . ?
C13 C15 1.383(8) . ?
C7 O1 1.246(6) . ?
C7 N1 1.320(7) . ?
C7 C4 1.498(7) . ?
C3 C6 1.390(8) . ?
C8 N1 1.464(6) . ?
C8 C9 1.499(9) . ?
C9 C10 1.303(10) . ?
C18 N2 1.442(7) . ?
C18 C19 1.481(11) . ?
C5 C6 1.373(8) . ?
C19 C20 1.296(12) . ?
C37 O4 1.254(6) . ?
C37 N4 1.323(7) . ?
C37 C31 1.488(7) . ?
C21 C25 1.392(7) . ?
C21 C22 1.394(7) . ?
C31 C32 1.405(7) . ?
C31 C33 1.407(7) . ?
C22 C23 1.404(7) . ?
C22 C27 1.501(7) . ?
C23 C26 1.374(7) . ?
C27 O3 1.241(6) . ?
C27 N3 1.326(7) . ?
C32 C35 1.378(8) . ?
C24 C26 1.377(8) . ?
C24 C25 1.392(7) . ?
C29 C30 1.306(9) . ?
C29 C28 1.489(8) . ?
C38 N4 1.463(7) . ?
C38 C39 1.484(9) . ?
C28 N3 1.473(6) . ?
C33 C34 1.389(7) . ?
C34 C36 1.378(8) . ?
C35 C36 1.376(8) . ?
C40 C39 1.329(9) . ?

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
C1 S1 S2 103.40(17) . . ?
C16 S2 S1 104.49(17) . . ?
C33 S4 S3 106.04(17) . . ?
C21 S3 S4 106.21(17) . . ?
O2 C17 N2 122.4(4) . . ?
O2 C17 C11 120.1(4) . . ?
N2 C17 C11 117.4(4) . . ?
C14 C16 C11 119.2(4) . . ?
C14 C16 S2 120.1(4) . . ?
C11 C16 S2 120.7(4) . . ?
C13 C11 C16 119.1(4) . . ?
C13 C11 C17 120.8(5) . . ?
C16 C11 C17 120.1(4) . . ?
C3 C1 C4 119.3(5) . . ?
C3 C1 S1 120.8(4) . . ?
C4 C1 S1 119.9(4) . . ?
C5 C2 C4 121.6(5) . . ?
C15 C12 C14 120.4(5) . . ?
C15 C13 C11 121.0(5) . . ?
O1 C7 N1 123.2(4) . . ?
O1 C7 C4 118.8(5) . . ?
N1 C7 C4 118.0(4) . . ?
C12 C14 C16 120.3(5) . . ?
C6 C3 C1 120.3(5) . . ?
N1 C8 C9 115.1(5) . . ?
C2 C4 C1 118.9(5) . . ?
C2 C4 C7 120.4(5) . . ?
C1 C4 C7 120.7(4) . . ?
C12 C15 C13 119.9(5) . . ?
C10 C9 C8 126.2(6) . . ?
N2 C18 C19 114.8(5) . . ?
C6 C5 C2 119.3(5) . . ?
C5 C6 C3 120.5(5) . . ?
C20 C19 C18 126.4(7) . . ?
O4 C37 N4 122.2(5) . . ?
O4 C37 C31 119.6(4) . . ?
N4 C37 C31 118.2(4) . . ?
C25 C21 C22 119.2(4) . . ?
C25 C21 S3 122.0(4) . . ?
C22 C21 S3 118.9(4) . . ?
C32 C31 C33 118.1(5) . . ?
C32 C31 C37 120.9(4) . . ?
C33 C31 C37 120.9(4) . . ?
C21 C22 C23 119.3(4) . . ?
C21 C22 C27 121.5(4) . . ?
C23 C22 C27 119.1(4) . . ?
C26 C23 C22 120.8(5) . . ?
O3 C27 N3 122.7(5) . . ?
O3 C27 C22 119.5(5) . . ?
N3 C27 C22 117.8(4) . . ?
C35 C32 C31 121.1(5) . . ?
C26 C24 C25 120.1(5) . . ?
C30 C29 C28 123.3(6) . . ?
N4 C38 C39 115.2(5) . . ?
N3 C28 C29 111.8(5) . . ?
C34 C33 C31 119.7(5) . . ?
C34 C33 S4 121.6(4) . . ?
C31 C33 S4 118.7(4) . . ?
C24 C25 C21 120.5(5) . . ?
C23 C26 C24 119.9(5) . . ?
C36 C34 C33 120.8(5) . . ?
C36 C35 C32 120.0(5) . . ?
C35 C36 C34 120.2(5) . . ?
C40 C39 C38 126.8(6) . . ?
C27 N3 C28 120.3(4) . . ?
C37 N4 C38 122.4(4) . . ?
C17 N2 C18 121.7(4) . . ?
C7 N1 C8 121.9(4) . . ?

_refine_diff_density_max         1.261
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.080


####################################################################### 
# 
# 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_compound3r
_database_code_depnum_ccdc_archive 'CCDC 2193309'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N O S'
_chemical_formula_weight         227.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   5.8819(4)
_cell_length_b                   14.3729(9)
_cell_length_c                   12.3134(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.232(5)
_cell_angle_gamma                90
_cell_volume                     1030.25(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2142
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.287
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13564
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         28.733
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2662
_reflns_number_gt                2055
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2662
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.62531(8) 0.49297(3) 0.65446(4) 0.02551(17) Uani 1 1 d . . . . .
C8 C 0.7420(3) 0.35265(12) 0.52451(13) 0.0196(4) Uani 1 1 d . . . . .
C7 C 1.0145(3) 0.39929(12) 0.68955(14) 0.0201(4) Uani 1 1 d . . . . .
C1 C 0.8274(3) 0.52666(13) 0.76428(14) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.8868(3) 0.34980(13) 0.44518(14) 0.0246(4) Uani 1 1 d . . . . .
H9 H 1.026688 0.383816 0.454806 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6184(3) 0.24835(14) 0.33702(15) 0.0276(4) Uani 1 1 d . . . . .
H10 H 0.576962 0.211505 0.273207 0.033 Uiso 1 1 calc R U . . .
C2 C 1.0250(3) 0.47243(13) 0.77300(13) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.9948(4) 0.61805(14) 0.91588(16) 0.0316(5) Uani 1 1 d . . . . .
H3 H 0.986506 0.667856 0.965889 0.038 Uiso 1 1 calc R U . . .
C11 C 0.5344(3) 0.30534(13) 0.51112(14) 0.0224(4) Uani 1 1 d . . . . .
H11 H 0.436301 0.308034 0.566010 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4724(3) 0.25393(14) 0.41594(15) 0.0266(4) Uani 1 1 d . . . . .
H12 H 0.329113 0.222356 0.404780 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8089(4) 0.60075(14) 0.83661(16) 0.0286(4) Uani 1 1 d . . . . .
H4 H 0.673603 0.637583 0.831266 0.034 Uiso 1 1 calc R U . . .
C13 C 0.8249(3) 0.29659(14) 0.35133(14) 0.0272(4) Uani 1 1 d . . . . .
H13 H 0.923992 0.293253 0.296947 0.033 Uiso 1 1 calc R U . . .
C5 C 1.1945(4) 0.56460(14) 0.92474(15) 0.0313(5) Uani 1 1 d . . . . .
H5 H 1.319816 0.578648 0.979959 0.038 Uiso 1 1 calc R U . . .
C6 C 1.2112(4) 0.49143(13) 0.85378(15) 0.0260(4) Uani 1 1 d . . . . .
H6 H 1.346676 0.454689 0.859744 0.031 Uiso 1 1 calc R U . . .
O1 O 1.1583(2) 0.33968(9) 0.67893(10) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.8068(3) 0.40716(10) 0.62143(12) 0.0220(3) 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
S1 N1 1.7175(15) . ?
S1 C1 1.7365(19) . ?
C8 C9 1.386(2) . ?
C8 C11 1.387(2) . ?
C8 N1 1.433(2) . ?
C7 O1 1.224(2) . ?
C7 N1 1.384(2) . ?
C7 C2 1.465(2) . ?
C1 C2 1.391(3) . ?
C1 C4 1.402(3) . ?
C9 C13 1.390(3) . ?
C10 C13 1.387(3) . ?
C10 C12 1.388(3) . ?
C2 C6 1.397(2) . ?
C3 C4 1.380(3) . ?
C3 C5 1.395(3) . ?
C11 C12 1.389(2) . ?
C5 C6 1.380(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C1 90.31(8) . . ?
C9 C8 C11 121.43(16) . . ?
C9 C8 N1 119.10(16) . . ?
C11 C8 N1 119.46(15) . . ?
O1 C7 N1 123.78(16) . . ?
O1 C7 C2 128.08(16) . . ?
N1 C7 C2 108.14(15) . . ?
C2 C1 C4 121.09(18) . . ?
C2 C1 S1 112.03(13) . . ?
C4 C1 S1 126.84(15) . . ?
C8 C9 C13 119.21(17) . . ?
C13 C10 C12 120.00(16) . . ?
C1 C2 C6 120.45(17) . . ?
C1 C2 C7 113.39(16) . . ?
C6 C2 C7 126.14(17) . . ?
C4 C3 C5 121.96(18) . . ?
C8 C11 C12 118.76(16) . . ?
C10 C12 C11 120.51(17) . . ?
C3 C4 C1 117.40(19) . . ?
C10 C13 C9 120.05(17) . . ?
C6 C5 C3 120.38(18) . . ?
C5 C6 C2 118.72(19) . . ?
C7 N1 C8 124.50(14) . . ?
C7 N1 S1 116.09(12) . . ?
C8 N1 S1 119.32(11) . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.060


####################################################################### 
# 
# 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_compound3h
_database_code_depnum_ccdc_archive 'CCDC 2193304'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N O2 S'
_chemical_formula_weight         195.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   10.5437(4)
_cell_length_b                   7.8373(3)
_cell_length_c                   10.7574(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.0875(18)
_cell_angle_gamma                90
_cell_volume                     865.84(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7489
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.63

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.335
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11299
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         28.781
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.913
_reflns_number_total             3902
_reflns_number_gt                3760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.742
_reflns_Friedel_fraction_full    0.825

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.38(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3902
_refine_ls_number_parameters     237
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   0.657
_refine_ls_restrained_S_all      0.657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.34153(5) 0.21468(7) 0.14744(5) 0.02217(13) Uani 1 1 d . . . . .
S1 S 0.13610(5) 0.45500(7) 0.88663(5) 0.02555(14) Uani 1 1 d . . . . .
C1 C -0.0386(2) 0.3553(3) 0.6903(2) 0.0196(4) Uani 1 1 d . . . . .
C7 C 0.0717(2) 0.4111(3) 0.6400(2) 0.0214(4) Uani 1 1 d . . . . .
C2 C -0.0195(2) 0.3778(3) 0.8221(2) 0.0217(4) Uani 1 1 d . . . . .
C9 C 0.4024(2) 0.4156(3) 0.7357(2) 0.0271(5) Uani 1 1 d . . . . .
H9A H 0.3767 0.3205 0.6747 0.032 Uiso 1 1 calc R U . . .
H9B H 0.4779 0.4739 0.7142 0.032 Uiso 1 1 calc R U . . .
C3 C -0.2344(2) 0.2821(3) 0.8148(3) 0.0312(5) Uani 1 1 d . . . . .
H3 H -0.3030 0.2582 0.8562 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2901(2) 0.5405(3) 0.7208(3) 0.0289(5) Uani 1 1 d . . . . .
H8A H 0.3154 0.6342 0.7833 0.035 Uiso 1 1 calc R U . . .
H8B H 0.2739 0.5911 0.6343 0.035 Uiso 1 1 calc R U . . .
C4 C -0.2548(2) 0.2563(3) 0.6826(3) 0.0311(5) Uani 1 1 d . . . . .
H4 H -0.3363 0.2144 0.6358 0.037 Uiso 1 1 calc R U . . .
C5 C -0.1165(2) 0.3417(3) 0.8862(2) 0.0278(5) Uani 1 1 d . . . . .
H5 H -0.1027 0.3573 0.9759 0.033 Uiso 1 1 calc R U . . .
C6 C -0.1570(2) 0.2917(3) 0.6205(2) 0.0259(5) Uani 1 1 d . . . . .
H6 H -0.1701 0.2730 0.5312 0.031 Uiso 1 1 calc R U . . .
O1 O 0.08028(18) 0.4180(2) 0.52735(16) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.44007(18) 0.3483(2) 0.86124(18) 0.0344(4) Uani 1 1 d . . . . .
H2 H 0.4772 0.4248 0.9112 0.052 Uiso 1 1 calc R U . . .
N1 N 0.1695(2) 0.4632(3) 0.7393(2) 0.0241(4) Uani 1 1 d . . . . .
C10 C 0.5314(2) 0.0794(3) 0.3135(2) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.6527(2) 0.0048(3) 0.3635(2) 0.0235(4) Uani 1 1 d . . . . .
H11 H 0.6771 -0.0276 0.4508 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4303(2) 0.1137(3) 0.3833(2) 0.0192(4) Uani 1 1 d . . . . .
C12 C 0.7364(2) -0.0207(3) 0.2828(3) 0.0275(5) Uani 1 1 d . . . . .
H12 H 0.8195 -0.0704 0.3151 0.033 Uiso 1 1 calc R U . . .
C13 C 0.6995(2) 0.0264(3) 0.1540(3) 0.0297(5) Uani 1 1 d . . . . .
H13 H 0.7579 0.0066 0.1000 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4968(2) 0.1276(3) 0.1862(2) 0.0191(4) Uani 1 1 d . . . . .
C18 C 0.0870(2) 0.1458(3) 0.2786(2) 0.0267(5) Uani 1 1 d . . . . .
H18A H 0.1033 0.0216 0.2886 0.032 Uiso 1 1 calc R U . . .
H18B H 0.0156 0.1758 0.3207 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2085(2) 0.2432(3) 0.3392(2) 0.0261(5) Uani 1 1 d . . . . .
H17A H 0.1950 0.3654 0.3167 0.031 Uiso 1 1 calc R U . . .
H17B H 0.2230 0.2336 0.4331 0.031 Uiso 1 1 calc R U . . .
C15 C 0.5804(2) 0.1008(3) 0.1038(2) 0.0257(5) Uani 1 1 d . . . . .
H15 H 0.5559 0.1327 0.0164 0.031 Uiso 1 1 calc R U . . .
O3 O 0.43414(15) 0.0878(2) 0.49749(16) 0.0272(4) Uani 1 1 d . . . . .
O4 O 0.05111(18) 0.1888(3) 0.14659(18) 0.0337(4) Uani 1 1 d . . . . .
H4A H 0.0277 0.1003 0.1035 0.051 Uiso 1 1 calc R U . . .
N2 N 0.32495(18) 0.1836(2) 0.30020(18) 0.0217(4) 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
S2 N2 1.709(2) . ?
S2 C14 1.735(2) . ?
S1 N1 1.700(2) . ?
S1 C2 1.739(2) . ?
C1 C2 1.396(3) . ?
C1 C6 1.396(3) . ?
C1 C7 1.457(3) . ?
C7 O1 1.237(3) . ?
C7 N1 1.368(3) . ?
C2 C5 1.387(3) . ?
C9 O2 1.420(3) . ?
C9 C8 1.516(3) . ?
C3 C5 1.386(4) . ?
C3 C4 1.404(4) . ?
C8 N1 1.463(3) . ?
C4 C6 1.378(4) . ?
C10 C14 1.387(3) . ?
C10 C11 1.398(3) . ?
C10 C16 1.461(3) . ?
C11 C12 1.386(3) . ?
C16 O3 1.236(3) . ?
C16 N2 1.373(2) . ?
C12 C13 1.401(4) . ?
C13 C15 1.380(3) . ?
C14 C15 1.401(3) . ?
C18 O4 1.425(3) . ?
C18 C17 1.507(3) . ?
C17 N2 1.461(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S2 C14 90.51(10) . . ?
N1 S1 C2 90.96(11) . . ?
C2 C1 C6 119.9(2) . . ?
C2 C1 C7 113.3(2) . . ?
C6 C1 C7 126.8(2) . . ?
O1 C7 N1 122.9(2) . . ?
O1 C7 C1 128.2(2) . . ?
N1 C7 C1 108.9(2) . . ?
C1 C2 C5 121.7(2) . . ?
C1 C2 S1 110.85(17) . . ?
C5 C2 S1 127.42(18) . . ?
O2 C9 C8 112.6(2) . . ?
C5 C3 C4 121.5(2) . . ?
N1 C8 C9 113.6(2) . . ?
C6 C4 C3 120.2(2) . . ?
C3 C5 C2 117.6(2) . . ?
C4 C6 C1 119.1(2) . . ?
C7 N1 C8 122.8(2) . . ?
C7 N1 S1 115.95(17) . . ?
C8 N1 S1 120.86(18) . . ?
C14 C10 C11 120.5(2) . . ?
C14 C10 C16 113.45(19) . . ?
C11 C10 C16 126.1(2) . . ?
C12 C11 C10 118.4(2) . . ?
O3 C16 N2 123.5(2) . . ?
O3 C16 C10 128.11(19) . . ?
N2 C16 C10 108.38(19) . . ?
C11 C12 C13 120.5(2) . . ?
C15 C13 C12 121.5(2) . . ?
C10 C14 C15 121.4(2) . . ?
C10 C14 S2 111.57(17) . . ?
C15 C14 S2 126.98(18) . . ?
O4 C18 C17 108.6(2) . . ?
N2 C17 C18 113.66(19) . . ?
C13 C15 C14 117.6(2) . . ?
C16 N2 C17 123.3(2) . . ?
C16 N2 S2 116.07(16) . . ?
C17 N2 S2 120.40(16) . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_compound3q
_database_code_depnum_ccdc_archive 'CCDC 2193308'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 N O S'
_chemical_formula_weight         189.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   4.1297(3)
_cell_length_b                   14.1058(11)
_cell_length_c                   14.7610(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.338(5)
_cell_angle_gamma                90
_cell_volume                     858.41(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4032
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      28.59

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11263
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.999
_diffrn_reflns_theta_max         28.802
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2232
_reflns_number_gt                1884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2232
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.92481(9) -0.01645(3) 0.38442(2) 0.02141(16) Uani 1 1 d . . . . .
C7 C 0.8492(4) 0.11354(11) 0.25715(10) 0.0230(3) Uani 1 1 d . . . . .
C1 C 1.0858(4) -0.03905(11) 0.27999(10) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.7984(4) 0.19712(11) 0.47721(10) 0.0226(3) Uani 1 1 d . . . . .
C2 C 1.2560(4) -0.11993(12) 0.25603(11) 0.0240(3) Uani 1 1 d . . . . .
H2 H 1.298857 -0.170041 0.298034 0.029 Uiso 1 1 calc R U . . .
C3 C 1.0275(4) 0.03525(11) 0.21909(10) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.6016(4) 0.15231(12) 0.40291(11) 0.0257(3) Uani 1 1 d . . . . .
H8A H 0.429042 0.113965 0.428940 0.031 Uiso 1 1 calc R U . . .
H8B H 0.495272 0.202418 0.364806 0.031 Uiso 1 1 calc R U . . .
C4 C 1.3596(4) -0.12418(12) 0.16877(11) 0.0284(4) Uani 1 1 d . . . . .
H4 H 1.476968 -0.178282 0.150813 0.034 Uiso 1 1 calc R U . . .
C10 C 0.9545(4) 0.23369(12) 0.53791(11) 0.0279(4) Uani 1 1 d . . . . .
H10 H 1.079115 0.262865 0.586346 0.034 Uiso 1 1 calc R U . . .
C5 C 1.1342(4) 0.02927(12) 0.13096(11) 0.0272(4) Uani 1 1 d . . . . .
H5 H 1.095339 0.079697 0.089073 0.033 Uiso 1 1 calc R U . . .
C6 C 1.2967(4) -0.05109(13) 0.10609(11) 0.0299(4) Uani 1 1 d . . . . .
H6 H 1.366314 -0.056899 0.046130 0.036 Uiso 1 1 calc R U . . .
O1 O 0.7620(3) 0.18846(9) 0.22077(8) 0.0322(3) Uani 1 1 d . . . . .
N1 N 0.7904(3) 0.09158(9) 0.34571(8) 0.0222(3) 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
S1 N1 1.7088(13) . ?
S1 C1 1.7433(15) . ?
C7 O1 1.2296(19) . ?
C7 N1 1.3788(19) . ?
C7 C3 1.458(2) . ?
C1 C3 1.393(2) . ?
C1 C2 1.396(2) . ?
C9 C10 1.190(2) . ?
C9 C8 1.469(2) . ?
C2 C4 1.382(2) . ?
C3 C5 1.400(2) . ?
C8 N1 1.4597(19) . ?
C4 C6 1.399(2) . ?
C5 C6 1.378(2) . ?

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
N1 S1 C1 90.04(7) . . ?
O1 C7 N1 122.95(15) . . ?
O1 C7 C3 128.63(15) . . ?
N1 C7 C3 108.42(13) . . ?
C3 C1 C2 121.48(14) . . ?
C3 C1 S1 111.88(12) . . ?
C2 C1 S1 126.65(12) . . ?
C10 C9 C8 179.22(17) . . ?
C4 C2 C1 117.34(15) . . ?
C1 C3 C5 120.16(15) . . ?
C1 C3 C7 113.18(14) . . ?
C5 C3 C7 126.66(14) . . ?
N1 C8 C9 113.17(12) . . ?
C2 C4 C6 121.91(16) . . ?
C6 C5 C3 118.79(15) . . ?
C5 C6 C4 120.30(15) . . ?
C7 N1 C8 123.10(13) . . ?
C7 N1 S1 116.46(10) . . ?
C8 N1 S1 120.27(11) . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.055


####################################################################### 
# 
# 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_compound3n
_database_code_depnum_ccdc_archive 'CCDC 2193307'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O S'
_chemical_formula_weight         242.29

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4192(5)
_cell_length_b                   8.7045(5)
_cell_length_c                   8.7097(5)
_cell_angle_alpha                83.598(2)
_cell_angle_beta                 65.260(2)
_cell_angle_gamma                73.566(2)
_cell_volume                     556.00(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7652
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.273
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11550
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.912
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2639
_reflns_number_gt                2370
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.3800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2639
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      1.607
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.56629(4) 0.51869(4) 0.19556(4) 0.02048(11) Uani 1 1 d D . . . .
C1 C 0.83397(17) 0.45692(16) -0.10109(16) 0.0213(3) Uani 1 1 d . . . . .
C9 C 0.60216(17) 0.15290(15) 0.34774(16) 0.0191(2) Uani 1 1 d . . . . .
C10 C 0.50261(18) 0.23010(16) 0.50335(17) 0.0228(3) Uani 1 1 d . . . . .
H10 H 0.395916 0.312521 0.516440 0.027 Uiso 1 1 calc R U . . .
C11 C 0.75606(18) 0.03015(15) 0.33014(17) 0.0220(3) Uani 1 1 d . . . . .
H11 H 0.827764 -0.026523 0.226076 0.026 Uiso 1 1 calc R U . . .
C8 C 0.54898(19) 0.20858(16) 0.20126(17) 0.0225(3) Uani 1 1 d . . . . .
H8A H 0.584729 0.116420 0.125918 0.027 Uiso 1 1 calc R U . . .
H8B H 0.415759 0.251484 0.244470 0.027 Uiso 1 1 calc R U . . .
C2 C 0.73438(17) 0.57924(16) 0.01821(16) 0.0198(2) Uani 1 1 d D . . . .
C13 C 0.69666(19) 0.07829(17) 0.61638(18) 0.0251(3) Uani 1 1 d . . . . .
H13 H 0.731238 0.052975 0.708858 0.030 Uiso 1 1 calc R U . . .
C7 C 0.77936(18) 0.30650(16) -0.04914(16) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.77081(19) 0.72857(16) -0.00813(18) 0.0248(3) Uani 1 1 d . . . . .
H3 H 0.702213 0.811783 0.073956 0.030 Uiso 1 1 calc R U . . .
C4 C 0.97310(19) 0.48296(19) -0.25204(18) 0.0291(3) Uani 1 1 d . . . . .
H4 H 1.041308 0.400125 -0.334614 0.035 Uiso 1 1 calc R U . . .
C5 C 0.9102(2) 0.75177(18) -0.15775(19) 0.0292(3) Uani 1 1 d . . . . .
H5 H 0.938397 0.852375 -0.177898 0.035 Uiso 1 1 calc R U . . .
C12 C 0.80330(18) -0.00832(16) 0.46727(18) 0.0246(3) Uani 1 1 d . . . . .
H12 H 0.907019 -0.092605 0.458955 0.030 Uiso 1 1 calc R U . . .
C6 C 1.0104(2) 0.6309(2) -0.2798(2) 0.0322(3) Uani 1 1 d . . . . .
H6 H 1.104418 0.650242 -0.382298 0.039 Uiso 1 1 calc R U . . .
N1 N 0.63634(15) 0.33275(13) 0.10503(14) 0.0206(2) Uani 1 1 d . . . . .
O1 O 0.84666(14) 0.17841(12) -0.12625(13) 0.0302(2) Uani 1 1 d . . . . .
N2 N 0.54704(17) 0.19606(14) 0.63610(15) 0.0259(2) 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
S1 N1 1.7159(11) . ?
S1 C2 1.7543(13) . ?
C1 C2 1.3888(19) . ?
C1 C4 1.3953(19) . ?
C1 C7 1.4713(18) . ?
C9 C10 1.3873(18) . ?
C9 C11 1.3896(18) . ?
C9 C8 1.5102(17) . ?
C10 N2 1.3369(18) . ?
C11 C12 1.3892(19) . ?
C8 N1 1.4641(16) . ?
C2 C3 1.3915(18) . ?
C13 N2 1.3397(18) . ?
C13 C12 1.386(2) . ?
C7 O1 1.2273(17) . ?
C7 N1 1.3655(17) . ?
C3 C5 1.383(2) . ?
C4 C6 1.382(2) . ?
C5 C6 1.395(2) . ?

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
N1 S1 C2 89.55(6) . . ?
C2 C1 C4 119.93(13) . . ?
C2 C1 C7 113.76(12) . . ?
C4 C1 C7 126.30(13) . . ?
C10 C9 C11 117.71(12) . . ?
C10 C9 C8 120.30(12) . . ?
C11 C9 C8 121.89(12) . . ?
N2 C10 C9 124.27(12) . . ?
C12 C11 C9 118.89(12) . . ?
N1 C8 C9 111.02(10) . . ?
C1 C2 C3 121.50(12) . . ?
C1 C2 S1 111.53(10) . . ?
C3 C2 S1 126.97(11) . . ?
N2 C13 C12 123.01(13) . . ?
O1 C7 N1 124.51(13) . . ?
O1 C7 C1 127.89(13) . . ?
N1 C7 C1 107.60(11) . . ?
C5 C3 C2 117.77(13) . . ?
C6 C4 C1 119.11(14) . . ?
C3 C5 C6 121.52(13) . . ?
C13 C12 C11 118.91(13) . . ?
C4 C6 C5 120.16(14) . . ?
C7 N1 C8 123.68(11) . . ?
C7 N1 S1 117.53(9) . . ?
C8 N1 S1 118.65(9) . . ?
C10 N2 C13 117.19(12) . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.046


####################################################################### 
# 
# 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_compound2j
_database_code_depnum_ccdc_archive 'CCDC 2193295'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Cl2 N2 O2 S2'
_chemical_formula_weight         429.36

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   10.7004(2)
_cell_length_b                   18.5647(4)
_cell_length_c                   11.2176(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.2724(12)
_cell_angle_gamma                90
_cell_volume                     1962.54(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8484
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.559
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29522
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         28.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5089
_reflns_number_gt                4161
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5089
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.08378(5) 0.11200(2) 0.61301(4) 0.02459(14) Uani 1 1 d . . . . .
S2 S -0.00120(5) 0.13325(2) 0.48581(4) 0.02417(14) Uani 1 1 d . . . . .
C7 C -0.2215(2) 0.15501(10) 0.78409(17) 0.0254(4) Uani 1 1 d . . . . .
C1 C 0.0863(2) 0.23069(11) 0.74554(18) 0.0293(4) Uani 1 1 d . . . . .
H1 H 0.1357 0.2214 0.6957 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0561(2) 0.25887(11) 0.89211(17) 0.0288(4) Uani 1 1 d . . . . .
H2 H -0.1048 0.2685 0.9425 0.035 Uiso 1 1 calc R U . . .
C3 C -0.02680(19) 0.18674(9) 0.72772(16) 0.0232(3) Uani 1 1 d . . . . .
C4 C -0.10098(19) 0.20175(10) 0.79967(17) 0.0237(4) Uani 1 1 d . . . . .
C5 C 0.0575(2) 0.30137(11) 0.91125(19) 0.0340(4) Uani 1 1 d . . . . .
H5 H 0.0878 0.3394 0.9755 0.041 Uiso 1 1 calc R U . . .
C8 C -0.4431(3) 0.15055(13) 0.7959(3) 0.0436(6) Uani 1 1 d . . . . .
H8A H -0.4296 0.0981 0.7909 0.052 Uiso 1 1 calc R U . . .
H8B H -0.5353 0.1639 0.7182 0.052 Uiso 1 1 calc R U . . .
C6 C 0.1273(2) 0.28808(12) 0.83586(19) 0.0338(4) Uani 1 1 d . . . . .
H6 H 0.2033 0.3184 0.8461 0.041 Uiso 1 1 calc R U . . .
C9 C -0.4462(3) 0.16742(12) 0.9260(3) 0.0474(6) Uani 1 1 d . . . . .
H9A H -0.5239 0.1400 0.9293 0.057 Uiso 1 1 calc R U . . .
H9B H -0.4653 0.2194 0.9288 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2147(2) 0.04657(10) 0.67568(18) 0.0281(4) Uani 1 1 d . . . . .
H10 H 0.1746 0.0550 0.7340 0.034 Uiso 1 1 calc R U . . .
C11 C 0.15476(19) 0.07878(9) 0.54872(16) 0.0214(3) Uani 1 1 d . . . . .
C12 C 0.2150(2) 0.06600(9) 0.46306(16) 0.0220(3) Uani 1 1 d . . . . .
C16 C 0.1551(2) 0.10159(10) 0.32852(18) 0.0283(4) Uani 1 1 d . . . . .
C13 C 0.3331(2) 0.02110(10) 0.50720(18) 0.0283(4) Uani 1 1 d . . . . .
H13 H 0.3735 0.0120 0.4494 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3923(2) -0.01042(10) 0.63434(18) 0.0306(4) Uani 1 1 d . . . . .
H14 H 0.4734 -0.0405 0.6638 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3326(2) 0.00212(10) 0.71811(19) 0.0307(4) Uani 1 1 d . . . . .
H15 H 0.3724 -0.0197 0.8050 0.037 Uiso 1 1 calc R U . . .
C17 C 0.0906(4) 0.0913(2) 0.0897(2) 0.0852(13) Uani 1 1 d . . . . .
H17A H 0.1121 0.1434 0.0940 0.102 Uiso 1 1 calc R U . A 1
H17B H -0.0139 0.0855 0.0432 0.102 Uiso 1 1 calc R U . A 1
O1 O -0.21758(16) 0.08902(8) 0.76985(15) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.11392(18) 0.16467(7) 0.31484(15) 0.0366(4) Uani 1 1 d . . . . .
N1 N -0.33029(18) 0.18886(9) 0.78663(17) 0.0304(4) Uani 1 1 d . . . . .
H1A H -0.3335 0.2362 0.7825 0.036 Uiso 1 1 calc R U . . .
N2 N 0.1496(2) 0.06245(11) 0.22603(16) 0.0453(5) Uani 1 1 d . . . . .
H2A H 0.1826 0.0181 0.2416 0.054 Uiso 1 1 calc R U . . .
Cl1 Cl -0.28047(11) 0.14447(5) 1.07026(8) 0.0727(3) Uani 1 1 d . . . . .
C18A C 0.1501(5) 0.0540(2) 0.0131(4) 0.0315(10) Uani 0.470(3) 1 d . . P B 1
H18A H 0.0892 0.0587 -0.0859 0.038 Uiso 0.470(3) 1 calc R U P B 1
H18B H 0.1686 0.0024 0.0378 0.038 Uiso 0.470(3) 1 calc R U P B 1
Cl2A Cl 0.31095(18) 0.10507(14) 0.07295(16) 0.0630(9) Uani 0.470(3) 1 d . . P B
1
C18B C 0.2302(6) 0.1287(2) 0.0693(4) 0.0351(9) Uani 0.530(3) 1 d . . P B 2
H18C H 0.2968 0.1553 0.1515 0.042 Uiso 0.530(3) 1 calc R U P B 2
H18D H 0.1935 0.1619 -0.0091 0.042 Uiso 0.530(3) 1 calc R U P B 2
Cl2B Cl 0.31503(13) 0.05202(10) 0.04128(11) 0.0468(5) Uani 0.530(3) 1 d . . P B
2


_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 C3 1.7915(18) . ?
S1 S2 2.0414(6) . ?
S2 C11 1.7861(18) . ?
C7 O1 1.239(2) . ?
C7 N1 1.335(3) . ?
C7 C4 1.494(3) . ?
C1 C6 1.390(3) . ?
C1 C3 1.393(3) . ?
C2 C5 1.378(3) . ?
C2 C4 1.399(2) . ?
C3 C4 1.402(2) . ?
C5 C6 1.390(3) . ?
C8 N1 1.447(3) . ?
C8 C9 1.508(3) . ?
C9 Cl1 1.796(3) . ?
C10 C15 1.390(3) . ?
C10 C11 1.390(2) . ?
C11 C12 1.408(2) . ?
C12 C13 1.394(3) . ?
C12 C16 1.486(2) . ?
C16 O2 1.235(2) . ?
C16 N2 1.338(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.383(3) . ?
C17 N2 1.452(3) . ?
C17 C18A 1.464(5) . ?
C17 C18B 1.758(7) . ?
C18A Cl2A 1.794(5) . ?
C18B Cl2B 1.795(5) . ?

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
C3 S1 S2 103.87(6) . . ?
C11 S2 S1 104.31(6) . . ?
O1 C7 N1 123.47(17) . . ?
O1 C7 C4 120.61(17) . . ?
N1 C7 C4 115.91(16) . . ?
C6 C1 C3 120.39(18) . . ?
C5 C2 C4 121.13(18) . . ?
C1 C3 C4 119.41(16) . . ?
C1 C3 S1 122.25(14) . . ?
C4 C3 S1 118.33(14) . . ?
C2 C4 C3 119.22(17) . . ?
C2 C4 C7 120.05(16) . . ?
C3 C4 C7 120.64(16) . . ?
C2 C5 C6 119.48(18) . . ?
N1 C8 C9 111.66(19) . . ?
C5 C6 C1 120.30(19) . . ?
C8 C9 Cl1 110.95(17) . . ?
C15 C10 C11 120.63(17) . . ?
C10 C11 C12 119.28(17) . . ?
C10 C11 S2 122.64(14) . . ?
C12 C11 S2 118.03(12) . . ?
C13 C12 C11 119.29(15) . . ?
C13 C12 C16 120.59(16) . . ?
C11 C12 C16 120.10(16) . . ?
O2 C16 N2 122.72(17) . . ?
O2 C16 C12 120.30(16) . . ?
N2 C16 C12 116.97(16) . . ?
C14 C13 C12 120.89(17) . . ?
C15 C14 C13 119.66(18) . . ?
C14 C15 C10 120.25(17) . . ?
N2 C17 C18A 110.5(2) . . ?
N2 C17 C18B 108.1(3) . . ?
C7 N1 C8 122.40(17) . . ?
C16 N2 C17 121.6(2) . . ?
C17 C18A Cl2A 97.9(3) . . ?
C17 C18B Cl2B 103.9(2) . . ?

_refine_diff_density_max         0.793
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.061


####################################################################### 
# 
# 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_compound3j
_database_code_depnum_ccdc_archive 'CCDC 2193305'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 Cl N O S'
_chemical_formula_weight         213.67

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   4.2898(4)
_cell_length_b                   10.1017(9)
_cell_length_c                   21.2306(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.654(7)
_cell_angle_gamma                90
_cell_volume                     919.03(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1690
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      23.47

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.597
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12819
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         28.720
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2371
_reflns_number_gt                1687
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2371
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.18651(16) 0.84940(7) 0.19050(3) 0.0238(2) Uani 1 1 d . . . . .
Cl1 Cl 0.16461(16) 1.20025(7) 0.16804(4) 0.0305(2) Uani 1 1 d . . . . .
C1 C -0.0036(6) 0.7123(3) 0.09276(13) 0.0215(5) Uani 1 1 d . . . . .
C2 C -0.0151(6) 0.7144(3) 0.15810(13) 0.0225(6) Uani 1 1 d . . . . .
C3 C -0.1480(7) 0.6113(3) 0.05795(15) 0.0293(6) Uani 1 1 d . . . . .
H3 H -0.1403 0.6096 0.0133 0.035 Uiso 1 1 calc R U . . .
C4 C -0.3021(7) 0.5138(3) 0.08917(17) 0.0342(7) Uani 1 1 d . . . . .
H4 H -0.4014 0.4441 0.0659 0.041 Uiso 1 1 calc R U . . .
C5 C -0.3141(7) 0.5163(3) 0.15436(16) 0.0342(7) Uani 1 1 d . . . . .
H5 H -0.4213 0.4477 0.1750 0.041 Uiso 1 1 calc R U . . .
C6 C -0.1746(7) 0.6158(3) 0.18986(15) 0.0289(6) Uani 1 1 d . . . . .
H6 H -0.1861 0.6174 0.2344 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1774(6) 0.8213(3) 0.06749(13) 0.0217(5) Uani 1 1 d . . . . .
O1 O 0.2362(5) 0.8429(2) 0.01242(9) 0.0285(5) Uani 1 1 d . . . . .
N1 N 0.2799(5) 0.9005(2) 0.11701(10) 0.0216(5) Uani 1 1 d . . . . .
C9 C 0.3446(7) 1.1425(3) 0.09784(13) 0.0246(6) Uani 1 1 d . . . . .
H9A H 0.1842 1.1356 0.0629 0.029 Uiso 1 1 calc R U . . .
H9B H 0.5031 1.2075 0.0854 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4982(6) 1.0091(3) 0.10842(14) 0.0239(6) Uani 1 1 d . . . . .
H8A H 0.6250 0.9886 0.0719 0.029 Uiso 1 1 calc R U . . .
H8B H 0.6419 1.0146 0.1462 0.029 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 N1 1.709(2) . ?
S1 C2 1.740(3) . ?
Cl1 C9 1.807(3) . ?
C1 C3 1.389(4) . ?
C1 C2 1.391(4) . ?
C1 C7 1.463(4) . ?
C2 C6 1.399(4) . ?
C3 C4 1.373(4) . ?
C4 C5 1.388(5) . ?
C5 C6 1.376(4) . ?
C7 O1 1.227(3) . ?
C7 N1 1.377(3) . ?
N1 C8 1.459(3) . ?
C9 C8 1.513(4) . ?

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
N1 S1 C2 90.53(12) . . ?
C3 C1 C2 120.4(3) . . ?
C3 C1 C7 126.1(3) . . ?
C2 C1 C7 113.5(2) . . ?
C1 C2 C6 120.7(3) . . ?
C1 C2 S1 111.5(2) . . ?
C6 C2 S1 127.8(2) . . ?
C4 C3 C1 118.9(3) . . ?
C3 C4 C5 120.6(3) . . ?
C6 C5 C4 121.6(3) . . ?
C5 C6 C2 117.8(3) . . ?
O1 C7 N1 123.5(2) . . ?
O1 C7 C1 128.3(2) . . ?
N1 C7 C1 108.3(2) . . ?
C7 N1 C8 121.7(2) . . ?
C7 N1 S1 116.19(18) . . ?
C8 N1 S1 121.35(18) . . ?
C8 C9 Cl1 111.41(19) . . ?
N1 C8 C9 114.3(2) . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.099


####################################################################### 
# 
# 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_compound2q
_database_code_depnum_ccdc_archive 'CCDC 2193299'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N3 O3 S2'
_chemical_formula_weight         453.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   11.755(16)
_cell_length_b                   7.717(10)
_cell_length_c                   24.95(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.228(17)
_cell_angle_gamma                90
_cell_volume                     2259(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1009
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      20.06

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15094
_diffrn_reflns_av_unetI/netI     0.1579
_diffrn_reflns_av_R_equivalents  0.1425
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_max         24.980
_diffrn_reflns_theta_full        24.980
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3962
_reflns_number_gt                2275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3962
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1613
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_ref         0.2685
_refine_ls_wR_factor_gt          0.2295
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.28411(15) 0.0572(2) 0.22312(6) 0.0400(5) Uani 1 1 d . . . . .
S2 S 0.28117(14) 0.0000(2) 0.30299(6) 0.0394(5) Uani 1 1 d . . . . .
C11 C 0.1385(6) 0.0500(8) 0.3215(2) 0.0372(15) Uani 1 1 d . . . . .
C7 C 0.3992(6) 0.2270(9) 0.1305(2) 0.0389(15) Uani 1 1 d . . . . .
C1 C 0.3837(5) 0.3440(8) 0.1780(2) 0.0353(15) Uani 1 1 d . . . . .
C12 C 0.1143(6) 0.0480(8) 0.3759(2) 0.0363(15) Uani 1 1 d . . . . .
C2 C 0.4197(5) 0.5168(9) 0.1776(3) 0.0429(16) Uani 1 1 d . . . . .
H2 H 0.453772 0.562421 0.146950 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0037(6) 0.0812(9) 0.3892(3) 0.0454(17) Uani 1 1 d . . . . .
H13 H -0.013956 0.077911 0.425862 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3568(6) 0.5571(8) 0.2659(3) 0.0446(17) Uani 1 1 d . . . . .
H3 H 0.349681 0.629041 0.296451 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3174(6) 0.3873(8) 0.2662(2) 0.0422(16) Uani 1 1 d . . . . .
H4 H 0.281146 0.345317 0.296715 0.051 Uiso 1 1 calc R U . . .
C5 C 0.3300(5) 0.2771(8) 0.2225(2) 0.0338(14) Uani 1 1 d . . . . .
C8 C 0.5168(6) 0.1421(9) 0.0587(3) 0.0463(17) Uani 1 1 d . . . . .
H8A H 0.575251 0.197325 0.037289 0.056 Uiso 1 1 calc R U . . .
H8B H 0.447180 0.125897 0.034956 0.056 Uiso 1 1 calc R U . . .
C17 C 0.2051(6) 0.0127(8) 0.4186(2) 0.0383(15) Uani 1 1 d . . . . .
C6 C 0.4058(6) 0.6202(8) 0.2214(3) 0.0443(17) Uani 1 1 d . . . . .
H6 H 0.430634 0.737306 0.220857 0.053 Uiso 1 1 calc R U . . .
C14 C 0.0531(6) 0.0921(9) 0.2826(2) 0.0468(18) Uani 1 1 d . . . . .
H14 H 0.070459 0.097647 0.245935 0.056 Uiso 1 1 calc R U . . .
C15 C -0.0556(6) 0.1255(11) 0.2969(3) 0.057(2) Uani 1 1 d . . . . .
H15 H -0.112910 0.153053 0.269862 0.068 Uiso 1 1 calc R U . . .
C20 C 0.2933(6) -0.2509(11) 0.5567(3) 0.0548(19) Uani 1 1 d . . . . .
H20 H 0.297649 -0.359877 0.574357 0.066 Uiso 1 1 calc R U . . .
C10 C 0.5913(6) -0.1667(10) 0.0928(3) 0.0517(19) Uani 1 1 d . . . . .
H10 H 0.617472 -0.277269 0.104788 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2809(6) 0.0549(9) 0.5096(3) 0.0487(18) Uani 1 1 d . . . . .
H18A H 0.268356 0.142311 0.537718 0.058 Uiso 1 1 calc R U . . .
H18B H 0.355033 0.080938 0.494467 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5584(6) -0.0278(9) 0.0777(2) 0.0441(17) Uani 1 1 d . . . . .
C16 C -0.0833(6) 0.1197(10) 0.3501(3) 0.0540(19) Uani 1 1 d . . . . .
H16 H -0.159010 0.141094 0.359841 0.065 Uiso 1 1 calc R U . . .
C19 C 0.2879(6) -0.1173(10) 0.5350(3) 0.0446(17) Uani 1 1 d . . . . .
O2 O 0.2918(4) -0.0689(6) 0.40724(17) 0.0470(12) Uani 1 1 d . . . . .
O1 O 0.3291(4) 0.1129(6) 0.11815(17) 0.0459(12) Uani 1 1 d . . . . .
N1 N 0.4912(5) 0.2551(7) 0.10275(18) 0.0416(13) Uani 1 1 d . . . . .
H1 H 0.536547 0.342815 0.111269 0.050 Uiso 1 1 calc R U . . .
N2 N 0.1919(5) 0.0734(7) 0.46740(19) 0.0448(14) Uani 1 1 d . . . . .
H2A H 0.127989 0.125983 0.474378 0.054 Uiso 1 1 calc R U . . .
C21 C 0.9564(9) 0.1660(11) 0.0382(3) 0.076(3) Uani 1 1 d . . . . .
H21 H 0.887505 0.159147 0.016481 0.091 Uiso 1 1 calc R U . . .
C22 C 1.0552(10) 0.1247(14) 0.1239(4) 0.104(4) Uani 1 1 d . . . . .
H22A H 1.042346 0.210261 0.151946 0.155 Uiso 1 1 calc R U . . .
H22B H 1.120905 0.159831 0.103971 0.155 Uiso 1 1 calc R U . . .
H22C H 1.070091 0.011127 0.140410 0.155 Uiso 1 1 calc R U . . .
C23 C 0.8537(9) 0.0485(14) 0.1093(6) 0.138(6) Uani 1 1 d . . . . .
H23A H 0.793822 0.035830 0.080647 0.206 Uiso 1 1 calc R U . . .
H23B H 0.828198 0.129258 0.136499 0.206 Uiso 1 1 calc R U . . .
H23C H 0.869790 -0.064611 0.125937 0.206 Uiso 1 1 calc R U . . .
O3 O 1.0413(7) 0.2237(9) 0.0175(2) 0.096(2) Uani 1 1 d . . . . .
N3 N 0.9547(5) 0.1141(7) 0.0873(2) 0.0504(15) 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
S1 C5 1.781(6) . ?
S1 S2 2.043(3) . ?
S2 C11 1.806(7) . ?
C11 C14 1.394(9) . ?
C11 C12 1.404(8) . ?
C7 O1 1.233(8) . ?
C7 N1 1.335(8) . ?
C7 C1 1.508(8) . ?
C1 C2 1.399(9) . ?
C1 C5 1.406(8) . ?
C12 C13 1.383(9) . ?
C12 C17 1.489(9) . ?
C2 C6 1.370(9) . ?
C13 C16 1.405(10) . ?
C3 C6 1.370(9) . ?
C3 C4 1.390(9) . ?
C4 C5 1.398(8) . ?
C8 N1 1.449(8) . ?
C8 C9 1.469(10) . ?
C17 O2 1.244(8) . ?
C17 N2 1.323(8) . ?
C14 C15 1.370(10) . ?
C15 C16 1.384(9) . ?
C20 C19 1.164(10) . ?
C10 C9 1.193(10) . ?
C18 N2 1.449(9) . ?
C18 C19 1.472(10) . ?
C21 O3 1.232(11) . ?
C21 N3 1.292(10) . ?
C22 N3 1.453(11) . ?
C23 N3 1.428(10) . ?

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
C5 S1 S2 103.7(2) . . ?
C11 S2 S1 105.7(2) . . ?
C14 C11 C12 119.9(6) . . ?
C14 C11 S2 121.0(5) . . ?
C12 C11 S2 119.1(5) . . ?
O1 C7 N1 122.4(6) . . ?
O1 C7 C1 121.1(5) . . ?
N1 C7 C1 116.5(6) . . ?
C2 C1 C5 120.3(5) . . ?
C2 C1 C7 121.0(5) . . ?
C5 C1 C7 118.6(5) . . ?
C13 C12 C11 118.3(6) . . ?
C13 C12 C17 120.6(6) . . ?
C11 C12 C17 121.1(6) . . ?
C6 C2 C1 120.0(6) . . ?
C12 C13 C16 122.1(6) . . ?
C6 C3 C4 119.6(6) . . ?
C3 C4 C5 121.3(6) . . ?
C4 C5 C1 117.7(6) . . ?
C4 C5 S1 121.8(5) . . ?
C1 C5 S1 120.5(4) . . ?
N1 C8 C9 111.8(5) . . ?
O2 C17 N2 121.9(6) . . ?
O2 C17 C12 119.6(5) . . ?
N2 C17 C12 118.5(6) . . ?
C3 C6 C2 121.0(6) . . ?
C15 C14 C11 120.6(6) . . ?
C14 C15 C16 121.1(7) . . ?
N2 C18 C19 115.0(6) . . ?
C10 C9 C8 179.2(9) . . ?
C15 C16 C13 118.1(7) . . ?
C20 C19 C18 177.7(7) . . ?
C7 N1 C8 120.3(6) . . ?
C17 N2 C18 121.2(6) . . ?
O3 C21 N3 124.5(10) . . ?
C21 N3 C23 122.2(9) . . ?
C21 N3 C22 121.5(8) . . ?
C23 N3 C22 116.3(9) . . ?

_refine_diff_density_max         0.814
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.108


####################################################################### 
# 
# 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_compound2r
_database_code_depnum_ccdc_archive 'CCDC 2193300'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 N2 O2 S2'
_chemical_formula_weight         456.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.2458(18)
_cell_length_b                   5.0506(4)
_cell_length_c                   18.4959(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.246(5)
_cell_angle_gamma                90
_cell_volume                     2125.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1150
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10641
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.790
_diffrn_reflns_theta_max         28.729
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2722
_reflns_number_gt                1717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2722
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_restrained_S_all      0.801
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.95686(2) 1.39454(11) 0.71487(3) 0.02191(19) Uani 1 1 d . . . . .
C7 C 0.84289(9) 1.1145(4) 0.61707(13) 0.0193(5) Uani 1 1 d . . . . .
C8 C 0.74991(9) 0.9547(4) 0.62777(13) 0.0198(5) Uani 1 1 d . . . . .
C1 C 0.95240(9) 1.1354(4) 0.64640(13) 0.0196(5) Uani 1 1 d . . . . .
C9 C 0.73392(10) 0.7739(4) 0.67337(13) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.759172 0.629867 0.696034 0.028 Uiso 1 1 calc R U . . .
C2 C 0.94393(10) 0.7402(5) 0.53760(14) 0.0256(5) Uani 1 1 d . . . . .
H2 H 0.941140 0.606482 0.500371 0.031 Uiso 1 1 calc R U . . .
C3 C 0.89423(10) 0.8252(4) 0.55086(13) 0.0222(5) Uani 1 1 d . . . . .
H3 H 0.857213 0.748423 0.522815 0.027 Uiso 1 1 calc R U . . .
C4 C 0.89771(9) 1.0231(4) 0.60514(13) 0.0182(5) Uani 1 1 d . . . . .
C10 C 0.68121(10) 0.8032(5) 0.68592(14) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.670303 0.678646 0.717050 0.031 Uiso 1 1 calc R U . . .
C5 C 0.99771(10) 0.8503(5) 0.57868(14) 0.0259(5) Uani 1 1 d . . . . .
H5 H 1.031993 0.791405 0.569702 0.031 Uiso 1 1 calc R U . . .
C11 C 0.64441(10) 1.0125(5) 0.65342(14) 0.0258(6) Uani 1 1 d . . . . .
H11 H 0.608578 1.034454 0.662852 0.031 Uiso 1 1 calc R U . . .
C6 C 1.00222(10) 1.0461(5) 0.63297(14) 0.0247(5) Uani 1 1 d . . . . .
H6 H 1.039566 1.119605 0.661138 0.030 Uiso 1 1 calc R U . . .
C12 C 0.66012(10) 1.1900(5) 0.60700(14) 0.0269(6) Uani 1 1 d . . . . .
H12 H 0.634627 1.333091 0.584116 0.032 Uiso 1 1 calc R U . . .
C13 C 0.71260(10) 1.1619(4) 0.59341(14) 0.0236(5) Uani 1 1 d . . . . .
H13 H 0.722848 1.283345 0.560916 0.028 Uiso 1 1 calc R U . . .
O1 O 0.83420(7) 1.3499(3) 0.62658(9) 0.0256(4) Uani 1 1 d . . . . .
N1 N 0.80467(8) 0.9183(4) 0.61730(12) 0.0229(5) Uani 1 1 d . . . . .
H1 H 0.8191(11) 0.767(5) 0.6214(13) 0.028(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.798(2) . ?
S1 S1 2.0455(11) 2_756 ?
C7 O1 1.231(2) . ?
C7 N1 1.358(3) . ?
C7 C4 1.494(3) . ?
C8 C13 1.385(3) . ?
C8 C9 1.386(3) . ?
C8 N1 1.418(3) . ?
C1 C6 1.390(3) . ?
C1 C4 1.401(3) . ?
C9 C10 1.384(3) . ?
C2 C5 1.379(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.399(3) . ?
C10 C11 1.380(3) . ?
C5 C6 1.386(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.387(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 S1 104.26(7) . 2_756 ?
O1 C7 N1 123.6(2) . . ?
O1 C7 C4 121.6(2) . . ?
N1 C7 C4 114.72(19) . . ?
C13 C8 C9 120.1(2) . . ?
C13 C8 N1 121.9(2) . . ?
C9 C8 N1 118.0(2) . . ?
C6 C1 C4 119.2(2) . . ?
C6 C1 S1 121.20(17) . . ?
C4 C1 S1 119.56(16) . . ?
C10 C9 C8 120.1(2) . . ?
C5 C2 C3 119.6(2) . . ?
C2 C3 C4 120.7(2) . . ?
C3 C4 C1 119.4(2) . . ?
C3 C4 C7 119.4(2) . . ?
C1 C4 C7 121.2(2) . . ?
C11 C10 C9 120.3(2) . . ?
C2 C5 C6 120.6(2) . . ?
C10 C11 C12 119.5(2) . . ?
C5 C6 C1 120.3(2) . . ?
C11 C12 C13 120.9(2) . . ?
C8 C13 C12 119.2(2) . . ?
C7 N1 C8 125.32(19) . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.071


####################################################################### 
# 
# 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_complex4
_database_code_depnum_ccdc_archive 'CCDC 2193310'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H43 Fe N6 O3a S2'
_chemical_formula_weight         727.73

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.1106(7)
_cell_length_b                   12.3582(6)
_cell_length_c                   13.7051(8)
_cell_angle_alpha                111.532(3)
_cell_angle_beta                 99.093(3)
_cell_angle_gamma                108.092(3)
_cell_volume                     1725.74(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9524
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.71

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.604
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24083
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6088
_reflns_number_gt                5254
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6088
_refine_ls_number_parameters     539
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6062(2) 0.6297(2) 0.74793(18) 0.0260(5) Uani 1 1 d . . . . .
H1 H 0.574563 0.593357 0.669921 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5963(2) 0.5499(2) 0.7977(2) 0.0339(6) Uani 1 1 d . . . . .
H2 H 0.558771 0.460328 0.755066 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6423(2) 0.6035(2) 0.9116(2) 0.0348(6) Uani 1 1 d . . . . .
H3 H 0.637225 0.551107 0.948430 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6956(2) 0.7339(2) 0.97058(19) 0.0303(5) Uani 1 1 d . . . . .
H4 H 0.728274 0.772298 1.048604 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7011(2) 0.8088(2) 0.91522(17) 0.0234(5) Uani 1 1 d . . . . .
C6 C 0.7527(2) 0.9510(2) 0.97160(17) 0.0275(5) Uani 1 1 d . . . . .
H6A H 0.729234 0.980638 1.039578 0.033 Uiso 1 1 calc R U . . .
H6B H 0.842888 0.985656 0.992227 0.033 Uiso 1 1 calc R U . . .
C7 C 0.6932(2) 1.10536(19) 0.94332(18) 0.0240(5) Uani 1 1 d . . . . .
C8 C 0.6250(2) 1.14529(19) 0.86942(18) 0.0233(5) Uani 1 1 d . . . . .
C9 C 0.5585(2) 1.2140(2) 0.91512(19) 0.0278(5) Uani 1 1 d . . . . .
H9 H 0.562038 1.236787 0.990053 0.033 Uiso 1 1 calc R U . . .
C10 C 0.4879(2) 1.2496(2) 0.8538(2) 0.0333(6) Uani 1 1 d . . . . .
H10 H 0.444515 1.297418 0.886942 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4804(2) 1.2157(2) 0.7443(2) 0.0356(6) Uani 1 1 d . . . . .
H11 H 0.430249 1.238136 0.701339 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5464(2) 1.1490(2) 0.6975(2) 0.0328(6) Uani 1 1 d . . . . .
H12 H 0.541052 1.125247 0.622049 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6208(2) 1.11630(19) 0.75996(19) 0.0257(5) Uani 1 1 d . . . . .
C14 C 0.4309(2) 0.86098(19) 0.75968(18) 0.0237(5) Uani 1 1 d . . . . .
H14 H 0.466598 0.899262 0.837379 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3099(2) 0.8331(2) 0.7184(2) 0.0302(5) Uani 1 1 d . . . . .
H15 H 0.262022 0.850561 0.766062 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2589(2) 0.7785(2) 0.6046(2) 0.0385(6) Uani 1 1 d . . . . .
H16 H 0.175664 0.760116 0.573163 0.046 Uiso 1 1 calc R U . . .
C17 C 0.3300(2) 0.7512(2) 0.5379(2) 0.0344(6) Uani 1 1 d . . . . .
H17 H 0.296271 0.714052 0.460023 0.041 Uiso 1 1 calc R U . . .
C18 C 0.4509(2) 0.7782(2) 0.58504(18) 0.0261(5) Uani 1 1 d . . . . .
C19 C 0.5337(2) 0.7455(3) 0.52003(19) 0.0343(6) Uani 1 1 d . . . . .
H19A H 0.491412 0.657406 0.460797 0.041 Uiso 1 1 calc R U . . .
H19B H 0.556884 0.803408 0.485523 0.041 Uiso 1 1 calc R U . . .
C20 C 0.7002(2) 0.6889(2) 0.54267(18) 0.0288(5) Uani 1 1 d . . . . .
C21 C 0.8079(2) 0.6836(2) 0.60991(18) 0.0248(5) Uani 1 1 d . . . . .
C22 C 0.8298(2) 0.5742(2) 0.5603(2) 0.0337(6) Uani 1 1 d . . . . .
H22 H 0.775422 0.508867 0.490640 0.040 Uiso 1 1 calc R U . . .
C23 C 0.9291(3) 0.5589(2) 0.6106(2) 0.0368(6) Uani 1 1 d . . . . .
H23 H 0.941988 0.483720 0.575961 0.044 Uiso 1 1 calc R U . . .
C24 C 1.0088(2) 0.6540(2) 0.7112(2) 0.0354(6) Uani 1 1 d . . . . .
H24 H 1.077418 0.645011 0.745994 0.042 Uiso 1 1 calc R U . . .
C25 C 0.9888(2) 0.7618(2) 0.7609(2) 0.0305(5) Uani 1 1 d . . . . .
H25 H 1.044434 0.826639 0.830292 0.037 Uiso 1 1 calc R U . . .
C26 C 0.8893(2) 0.7791(2) 0.71283(18) 0.0237(5) Uani 1 1 d . . . . .
C27 C 0.2902(2) 0.4714(2) 0.8114(2) 0.0342(6) Uani 1 1 d . . . . .
C28 C 0.2984(3) 0.5660(3) 0.7710(2) 0.0463(7) Uani 1 1 d . . . . .
H28A H 0.276644 0.631688 0.819342 0.069 Uiso 1 1 calc R U . . .
H28B H 0.242108 0.525474 0.696036 0.069 Uiso 1 1 calc R U . . .
H28C H 0.382066 0.604834 0.770374 0.069 Uiso 1 1 calc R U . . .
C29 C 1.0644(6) -0.0683(7) 0.4383(4) 0.0394(18) Uani 0.462(7) 1 d D . P A 2
H29A H 1.058(8) -0.057(8) 0.370(4) 0.059 Uiso 0.462(7) 1 d D U P A 2
H29B H 1.153(2) -0.028(8) 0.482(6) 0.059 Uiso 0.462(7) 1 d D U P A 2
C30 C 1.0665(5) 0.1420(5) 0.5249(5) 0.0480(17) Uani 0.538(7) 1 d D . P A 1
H30A H 1.153(2) 0.171(6) 0.569(5) 0.072 Uiso 0.538(7) 1 d D U P A 1
H30B H 1.049(6) 0.148(6) 0.454(3) 0.072 Uiso 0.538(7) 1 d D U P A 1
C31 C 1.0072(4) 0.2233(3) 0.5944(3) 0.0753(12) Uani 1 1 d . . . . .
H31A H 1.027801 0.230916 0.669411 0.113 Uiso 1 1 calc R U . A 1
H31B H 0.918361 0.182445 0.560764 0.113 Uiso 1 1 calc R U . A 1
H31C H 1.037944 0.307969 0.597139 0.113 Uiso 1 1 calc R U . A 1
C32 C 0.8664(5) -0.0453(5) 0.4355(4) 0.0386(14) Uani 0.528(6) 1 d D . P A 1
H32A H 0.841(6) -0.126(3) 0.443(5) 0.058 Uiso 0.528(6) 1 d D U P A 1
H32B H 0.845(6) 0.015(7) 0.493(5) 0.058 Uiso 0.528(6) 1 d D U P A 1
C33 C 0.9995(5) 0.0050(5) 0.3911(4) 0.0278(14) Uani 0.472(6) 1 d D . P A 2
H33A H 1.063(5) -0.031(7) 0.383(5) 0.042 Uiso 0.472(6) 1 d D U P A 2
H33B H 1.051(5) 0.0976(15) 0.420(5) 0.042 Uiso 0.472(6) 1 d D U P A 2
C34 C 0.8580(3) -0.0455(3) 0.3179(2) 0.0559(8) Uani 1 1 d . . . . .
H34A H 0.832693 -0.132559 0.261297 0.084 Uiso 1 1 calc R U . A 1
H34B H 0.938084 0.007779 0.319514 0.084 Uiso 1 1 calc R U . A 1
H34C H 0.798064 -0.011865 0.300707 0.084 Uiso 1 1 calc R U . A 1
C35 C 1.0000(6) 0.5253(5) 0.1156(4) 0.0447(16) Uani 0.522(7) 1 d D . P B 2
H35A H 0.960(11) 0.586(10) 0.133(6) 0.067 Uiso 0.522(7) 1 d D U P B 2
H35B H 0.961(8) 0.442(3) 0.118(5) 0.067 Uiso 0.522(7) 1 d D U P B 2
C36 C 0.8589(5) 0.4418(5) -0.0653(5) 0.0355(16) Uani 0.478(7) 1 d D . P B 1
H36A H 0.819(5) 0.369(4) -0.050(5) 0.053 Uiso 0.478(7) 1 d D U P B 1
H36B H 0.822(5) 0.495(5) -0.018(5) 0.053 Uiso 0.478(7) 1 d D U P B 1
C37 C 1.1490(4) 0.5761(3) 0.1883(3) 0.0776(13) Uani 1 1 d . . . . .
H37A H 1.201212 0.636470 0.167351 0.116 Uiso 1 1 calc R U . B 2
H37B H 1.171550 0.503222 0.171974 0.116 Uiso 1 1 calc R U . B 2
H37C H 1.159806 0.617852 0.267384 0.116 Uiso 1 1 calc R U . B 2
C38 C 0.9453(5) 0.5848(6) 0.0511(5) 0.0444(18) Uani 0.494(7) 1 d D . P B 1
H38A H 0.8551(13) 0.534(6) 0.025(6) 0.067 Uiso 0.494(7) 1 d D U P B 1
H38B H 0.963(12) 0.596(12) 0.129(3) 0.067 Uiso 0.494(7) 1 d D U P B 1
C39 C 0.9440(5) 0.3733(5) 0.0083(5) 0.0418(16) Uani 0.506(7) 1 d D . P B 2
H39A H 0.944(8) 0.405(6) 0.087(2) 0.063 Uiso 0.506(7) 1 d D U P B 2
H39B H 0.857(2) 0.343(6) -0.035(5) 0.063 Uiso 0.506(7) 1 d D U P B 2
C40 C 0.9880(3) 0.7127(3) 0.0290(4) 0.0785(12) Uani 1 1 d . . . . .
H40A H 0.963497 0.686912 -0.050517 0.118 Uiso 1 1 calc R U . B 1
H40B H 1.076842 0.758691 0.059829 0.118 Uiso 1 1 calc R U . B 1
H40C H 0.948724 0.767972 0.064483 0.118 Uiso 1 1 calc R U . B 1
Fe1 Fe 0.68152(3) 0.88304(3) 0.74396(2) 0.01841(12) Uani 1 1 d . . . . .
N1 N 0.65839(16) 0.75611(16) 0.80486(14) 0.0197(4) Uani 1 1 d . . . . .
N2 N 0.70418(17) 0.99504(16) 0.89559(14) 0.0223(4) Uani 1 1 d . . . . .
N3 N 0.50152(16) 0.83674(16) 0.69545(14) 0.0202(4) Uani 1 1 d . . . . .
N4 N 0.64306(17) 0.75793(17) 0.59440(14) 0.0234(4) Uani 1 1 d . . . . .
N5 N 0.2815(2) 0.3968(2) 0.8426(2) 0.0498(6) Uani 1 1 d . . . . .
N6 N 1.000000 0.000000 0.500000 0.0286(6) Uani 1 2 d S . P . .
N7 N 1.000000 0.500000 0.000000 0.0330(7) Uani 1 2 d S . P . .
O1 O 0.72822(17) 1.17293(15) 1.04466(13) 0.0360(4) Uani 1 1 d . . . . .
O2 O 0.6652(2) 0.6232(2) 0.44062(14) 0.0526(6) Uani 1 1 d . . . . .
O3a O 0.8332(3) 1.1424(3) 0.7548(3) 0.0277(10) Uani 0.494(4) 1 d . . P C 1
O3b O 0.6678(3) 1.0058(3) 0.5795(2) 0.0317(10) Uani 0.506(4) 1 d . . P C 2
S1 S 0.71429(6) 1.04428(5) 0.69965(5) 0.02721(16) Uani 1 1 d . . . . .
S2 S 0.88052(5) 0.92553(5) 0.78055(5) 0.03130(17) 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
C1 N1 1.336(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.342(3) . ?
C5 C6 1.498(3) . ?
C6 N2 1.465(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O1 1.245(3) . ?
C7 N2 1.338(3) . ?
C7 C8 1.519(3) . ?
C8 C13 1.397(3) . ?
C8 C9 1.398(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 S1 1.772(2) . ?
C14 N3 1.342(3) . ?
C14 C15 1.366(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 N3 1.348(3) . ?
C18 C19 1.494(3) . ?
C19 N4 1.466(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O2 1.249(3) . ?
C20 N4 1.337(3) . ?
C20 C21 1.507(3) . ?
C21 C22 1.402(3) . ?
C21 C26 1.404(3) . ?
C22 C23 1.390(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(3) . ?
C25 H25 0.9500 . ?
C26 S2 1.750(2) . ?
C27 N5 1.135(3) . ?
C27 C28 1.451(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 N6 1.459(5) . ?
C29 C31 1.684(8) 2_756 ?
C29 H29A 1.000(5) . ?
C29 H29B 1.000(5) . ?
C29 H33A 1.03(6) . ?
C30 C31 1.547(7) . ?
C30 N6 1.562(5) . ?
C30 C32 1.823(8) 2_756 ?
C30 H30A 1.000(5) . ?
C30 H30B 1.000(5) . ?
C30 H32A 1.23(6) 2_756 ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 N6 1.528(5) . ?
C32 C34 1.598(6) . ?
C32 H32A 1.001(5) . ?
C32 H32B 1.001(5) . ?
C33 N6 1.516(5) . ?
C33 C34 1.633(6) . ?
C33 H29A 1.19(7) . ?
C33 H33A 1.000(5) . ?
C33 H33B 1.001(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 N7 1.498(5) . ?
C35 C37 1.706(7) . ?
C35 H35A 1.000(5) . ?
C35 H35B 1.001(5) . ?
C35 H39A 1.29(7) . ?
C36 H36A 1.000(5) . ?
C36 N7 1.588(5) . ?
C36 C37 1.600(7) 2_765 ?
C36 H36A 1.000(5) . ?
C36 H36B 1.000(5) . ?
C36 H38A 1.36(7) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 N7 1.437(5) . ?
C38 C40 1.658(8) . ?
C38 H36B 1.45(6) . ?
C38 H38A 1.001(5) . ?
C38 H38B 1.000(5) . ?
C39 H39B 1.001(5) . ?
C39 C40 1.532(7) 2_765 ?
C39 N7 1.556(5) . ?
C39 H35B 1.37(6) . ?
C39 H39A 1.001(5) . ?
C39 H39B 1.001(5) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
Fe1 N4 1.9321(17) . ?
Fe1 N2 1.9449(17) . ?
Fe1 N1 1.9994(17) . ?
Fe1 N3 2.0024(18) . ?
Fe1 S1 2.2294(6) . ?
Fe1 S2 2.2302(7) . ?
O3a S1 1.419(3) . ?
O3b S1 1.490(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.7(2) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.9(2) . . ?
N1 C5 C6 115.19(18) . . ?
C4 C5 C6 123.9(2) . . ?
N2 C6 C5 108.36(17) . . ?
N2 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
N2 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
O1 C7 N2 124.2(2) . . ?
O1 C7 C8 118.02(18) . . ?
N2 C7 C8 117.65(18) . . ?
C13 C8 C9 117.9(2) . . ?
C13 C8 C7 125.58(19) . . ?
C9 C8 C7 116.45(19) . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 S1 118.63(17) . . ?
C8 C13 S1 121.05(17) . . ?
N3 C14 C15 123.0(2) . . ?
N3 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C14 C15 C16 118.0(2) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
N3 C18 C17 120.9(2) . . ?
N3 C18 C19 115.46(19) . . ?
C17 C18 C19 123.7(2) . . ?
N4 C19 C18 108.72(18) . . ?
N4 C19 H19A 109.9 . . ?
C18 C19 H19A 109.9 . . ?
N4 C19 H19B 109.9 . . ?
C18 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
O2 C20 N4 123.0(2) . . ?
O2 C20 C21 117.8(2) . . ?
N4 C20 C21 119.15(19) . . ?
C22 C21 C26 118.4(2) . . ?
C22 C21 C20 115.3(2) . . ?
C26 C21 C20 126.24(19) . . ?
C23 C22 C21 121.6(2) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 122.0(2) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C25 C26 C21 118.79(19) . . ?
C25 C26 S2 117.25(17) . . ?
C21 C26 S2 123.77(17) . . ?
N5 C27 C28 178.7(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N6 C29 C31 108.1(4) . 2_756 ?
N6 C29 H29A 107(4) . . ?
C31 C29 H29A 110(5) 2_756 . ?
N6 C29 H29B 109(4) . . ?
C31 C29 H29B 115(6) 2_756 . ?
H29A C29 H29B 107(8) . . ?
N6 C29 H33A 94.7(15) . . ?
C31 C29 H33A 125(4) 2_756 . ?
H29A C29 H33A 16(7) . . ?
H29B C29 H33A 102(7) . . ?
C31 C30 N6 110.0(4) . . ?
C31 C30 C32 125.3(4) . 2_756 ?
N6 C30 C32 53.0(2) . 2_756 ?
C31 C30 H30A 109(4) . . ?
N6 C30 H30A 107(4) . . ?
C32 C30 H30A 54(4) 2_756 . ?
C31 C30 H30B 104(4) . . ?
N6 C30 H30B 108(4) . . ?
C32 C30 H30B 131(4) 2_756 . ?
H30A C30 H30B 119(6) . . ?
C31 C30 H32A 129(3) . 2_756 ?
N6 C30 H32A 83.2(13) . 2_756 ?
C32 C30 H32A 31.3(11) 2_756 2_756 ?
H30A C30 H32A 26(4) . 2_756 ?
H30B C30 H32A 120(5) . 2_756 ?
C30 C31 C29 68.1(3) . 2_756 ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N6 C32 C34 109.5(3) . . ?
N6 C32 C30 54.7(2) . 2_756 ?
C34 C32 C30 120.6(4) . 2_756 ?
N6 C32 H32A 93(4) . . ?
C34 C32 H32A 122(4) . . ?
C30 C32 H32A 40(4) 2_756 . ?
N6 C32 H32B 97(4) . . ?
C34 C32 H32B 122(6) . . ?
C30 C32 H32B 117(5) 2_756 . ?
H32A C32 H32B 107(7) . . ?
N6 C33 C34 108.3(3) . . ?
N6 C33 H29A 94.2(5) . . ?
C34 C33 H29A 122(4) . . ?
N6 C33 H33A 93(4) . . ?
C34 C33 H33A 133(4) . . ?
H29A C33 H33A 11(8) . . ?
N6 C33 H33B 99(3) . . ?
C34 C33 H33B 117(4) . . ?
H29A C33 H33B 111(6) . . ?
H33A C33 H33B 100(6) . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N7 C35 C37 105.2(4) . . ?
N7 C35 H35A 102(4) . . ?
C37 C35 H35A 119(7) . . ?
N7 C35 H35B 109(4) . . ?
C37 C35 H35B 102(5) . . ?
H35A C35 H35B 119(9) . . ?
N7 C35 H39A 91.6(7) . . ?
C37 C35 H39A 110(4) . . ?
H35A C35 H39A 123(9) . . ?
H35B C35 H39A 17(4) . . ?
H36A C36 N7 106(4) . . ?
H36A C36 C37 122(4) . 2_765 ?
N7 C36 C37 106.1(4) . 2_765 ?
H36A C36 H36A 0(6) . . ?
N7 C36 H36A 106(4) . . ?
C37 C36 H36A 122(4) 2_765 . ?
H36A C36 H36B 92(5) . . ?
N7 C36 H36B 107(4) . . ?
C37 C36 H36B 122(4) 2_765 . ?
H36A C36 H36B 92(5) . . ?
H36A C36 H38A 97(5) . . ?
N7 C36 H38A 84.0(11) . . ?
C37 C36 H38A 133(3) 2_765 . ?
H36A C36 H38A 97(5) . . ?
H36B C36 H38A 23(4) . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N7 C38 C40 111.7(4) . . ?
N7 C38 H36B 93.4(7) . . ?
C40 C38 H36B 112(3) . . ?
N7 C38 H38A 107(4) . . ?
C40 C38 H38A 115(5) . . ?
H36B C38 H38A 18(5) . . ?
N7 C38 H38B 104(4) . . ?
C40 C38 H38B 119(7) . . ?
H36B C38 H38B 114(9) . . ?
H38A C38 H38B 99(10) . . ?
H39B C39 C40 118(4) . 2_765 ?
H39B C39 N7 100(4) . . ?
C40 C39 N7 112.3(4) 2_765 . ?
H39B C39 H35B 110(6) . . ?
C40 C39 H35B 121(4) 2_765 . ?
N7 C39 H35B 88.9(5) . . ?
H39B C39 H39A 104(7) . . ?
C40 C39 H39A 118(5) 2_765 . ?
N7 C39 H39A 101(4) . . ?
H35B C39 H39A 13(4) . . ?
H39B C39 H39B 0(8) . . ?
C40 C39 H39B 118(4) 2_765 . ?
N7 C39 H39B 100(4) . . ?
H35B C39 H39B 110(6) . . ?
H39A C39 H39B 104(7) . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N4 Fe1 N2 173.43(8) . . ?
N4 Fe1 N1 93.74(7) . . ?
N2 Fe1 N1 81.59(7) . . ?
N4 Fe1 N3 81.52(7) . . ?
N2 Fe1 N3 93.93(7) . . ?
N1 Fe1 N3 91.54(7) . . ?
N4 Fe1 S1 94.05(6) . . ?
N2 Fe1 S1 90.67(5) . . ?
N1 Fe1 S1 172.20(5) . . ?
N3 Fe1 S1 89.88(5) . . ?
N4 Fe1 S2 93.09(6) . . ?
N2 Fe1 S2 91.57(6) . . ?
N1 Fe1 S2 90.37(5) . . ?
N3 Fe1 S2 174.39(5) . . ?
S1 Fe1 S2 88.94(2) . . ?
C1 N1 C5 119.32(18) . . ?
C1 N1 Fe1 127.07(15) . . ?
C5 N1 Fe1 113.60(14) . . ?
C7 N2 C6 115.34(17) . . ?
C7 N2 Fe1 133.59(15) . . ?
C6 N2 Fe1 110.86(13) . . ?
C14 N3 C18 119.04(19) . . ?
C14 N3 Fe1 127.37(15) . . ?
C18 N3 Fe1 113.56(14) . . ?
C20 N4 C19 113.36(18) . . ?
C20 N4 Fe1 133.75(16) . . ?
C19 N4 Fe1 112.58(14) . . ?
C29 N6 C33 65.1(3) . . ?
C29 N6 C33 114.9(3) 2_756 . ?
C33 N6 C33 180.0 2_756 . ?
C32 N6 C32 180.0 . 2_756 ?
C32 N6 C30 72.3(3) . 2_756 ?
C32 N6 C30 107.7(3) 2_756 2_756 ?
C32 N6 C30 107.7(3) . . ?
C32 N6 C30 72.3(3) 2_756 . ?
C30 N6 C30 180.0 2_756 . ?
C38 N7 C38 180.0(3) 2_765 . ?
C38 N7 C35 63.0(4) 2_765 2_765 ?
C38 N7 C35 117.0(4) . 2_765 ?
C35 N7 C35 180.0(5) 2_765 . ?
C38 N7 C39 110.1(3) 2_765 2_765 ?
C38 N7 C39 69.9(3) . 2_765 ?
C35 N7 C39 110.7(3) 2_765 . ?
C35 N7 C39 69.3(3) . . ?
C39 N7 C39 180.0 2_765 . ?
C38 N7 C36 69.9(3) 2_765 2_765 ?
C38 N7 C36 110.1(3) . 2_765 ?
C38 N7 C36 110.1(3) 2_765 . ?
C38 N7 C36 69.9(3) . . ?
C36 N7 C36 180.0 2_765 . ?
O3a S1 C13 103.01(14) . . ?
O3b S1 C13 105.29(15) . . ?
O3a S1 Fe1 114.19(13) . . ?
O3b S1 Fe1 114.61(12) . . ?
C13 S1 Fe1 102.38(7) . . ?
C26 S2 Fe1 105.37(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
N1 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 N1 -1.8(3) . . . . ?
C3 C4 C5 C6 177.6(2) . . . . ?
N1 C5 C6 N2 20.2(3) . . . . ?
C4 C5 C6 N2 -159.3(2) . . . . ?
O1 C7 C8 C13 153.2(2) . . . . ?
N2 C7 C8 C13 -31.3(3) . . . . ?
O1 C7 C8 C9 -28.5(3) . . . . ?
N2 C7 C8 C9 146.9(2) . . . . ?
C13 C8 C9 C10 1.8(3) . . . . ?
C7 C8 C9 C10 -176.6(2) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C8 3.1(4) . . . . ?
C11 C12 C13 S1 -174.07(19) . . . . ?
C9 C8 C13 C12 -3.7(3) . . . . ?
C7 C8 C13 C12 174.5(2) . . . . ?
C9 C8 C13 S1 173.35(17) . . . . ?
C7 C8 C13 S1 -8.5(3) . . . . ?
N3 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C17 1.8(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 N3 -3.4(4) . . . . ?
C16 C17 C18 C19 176.3(2) . . . . ?
N3 C18 C19 N4 13.9(3) . . . . ?
C17 C18 C19 N4 -165.9(2) . . . . ?
O2 C20 C21 C22 -22.9(3) . . . . ?
N4 C20 C21 C22 153.9(2) . . . . ?
O2 C20 C21 C26 153.8(2) . . . . ?
N4 C20 C21 C26 -29.3(3) . . . . ?
C26 C21 C22 C23 0.1(4) . . . . ?
C20 C21 C22 C23 177.1(2) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C25 0.6(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C21 -0.5(3) . . . . ?
C24 C25 C26 S2 -175.70(19) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C20 C21 C26 C25 -176.2(2) . . . . ?
C22 C21 C26 S2 175.33(18) . . . . ?
C20 C21 C26 S2 -1.3(3) . . . . ?
C2 C1 N1 C5 -1.4(3) . . . . ?
C2 C1 N1 Fe1 178.94(17) . . . . ?
C4 C5 N1 C1 2.2(3) . . . . ?
C6 C5 N1 C1 -177.2(2) . . . . ?
C4 C5 N1 Fe1 -178.06(17) . . . . ?
C6 C5 N1 Fe1 2.5(2) . . . . ?
O1 C7 N2 C6 4.8(3) . . . . ?
C8 C7 N2 C6 -170.42(19) . . . . ?
O1 C7 N2 Fe1 -169.41(18) . . . . ?
C8 C7 N2 Fe1 15.4(3) . . . . ?
C5 C6 N2 C7 150.72(19) . . . . ?
C5 C6 N2 Fe1 -33.8(2) . . . . ?
C15 C14 N3 C18 -2.4(3) . . . . ?
C15 C14 N3 Fe1 175.36(16) . . . . ?
C17 C18 N3 C14 4.5(3) . . . . ?
C19 C18 N3 C14 -175.2(2) . . . . ?
C17 C18 N3 Fe1 -173.58(18) . . . . ?
C19 C18 N3 Fe1 6.7(2) . . . . ?
O2 C20 N4 C19 1.9(3) . . . . ?
C21 C20 N4 C19 -174.8(2) . . . . ?
O2 C20 N4 Fe1 -171.1(2) . . . . ?
C21 C20 N4 Fe1 12.2(3) . . . . ?
C18 C19 N4 C20 156.6(2) . . . . ?
C18 C19 N4 Fe1 -28.8(2) . . . . ?
C31 C29 N6 C33 62.7(4) 2_756 . . 2_756 ?
C31 C29 N6 C33 -117.3(4) 2_756 . . . ?
C34 C33 N6 C29 125.2(4) . . . . ?
C34 C33 N6 C29 -54.8(4) . . . 2_756 ?
C34 C32 N6 C30 -114.3(4) . . . 2_756 ?
C34 C32 N6 C30 65.7(4) . . . . ?
C30 C32 N6 C30 180.000(1) 2_756 . . . ?
C31 C30 N6 C32 60.3(4) . . . . ?
C32 C30 N6 C32 179.999(0) 2_756 . . . ?
C31 C30 N6 C32 -119.7(4) . . . 2_756 ?
C40 C38 N7 C36 72.3(5) . . . 2_765 ?
C40 C38 N7 C36 -107.7(5) . . . . ?
C37 C35 N7 C39 -72.8(4) . . . 2_765 ?
C37 C35 N7 C39 107.2(4) . . . . ?
H39B C39 N7 C35 -69(4) . . . 2_765 ?
C40 C39 N7 C35 57.8(5) 2_765 . . 2_765 ?
H39B C39 N7 C35 111(4) . . . . ?
C40 C39 N7 C35 -122.2(5) 2_765 . . . ?
H36A C36 N7 C38 71(4) . . . 2_765 ?
C37 C36 N7 C38 -59.8(4) 2_765 . . 2_765 ?
H36A C36 N7 C38 -109(4) . . . . ?
C37 C36 N7 C38 120.2(4) 2_765 . . . ?
C12 C13 S1 O3a 107.6(2) . . . . ?
C8 C13 S1 O3a -69.6(2) . . . . ?
C12 C13 S1 O3b -13.5(2) . . . . ?
C8 C13 S1 O3b 169.3(2) . . . . ?
C12 C13 S1 Fe1 -133.67(18) . . . . ?
C8 C13 S1 Fe1 49.20(19) . . . . ?
C25 C26 S2 Fe1 -148.53(17) . . . . ?
C21 C26 S2 Fe1 36.5(2) . . . . ?

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.058




####################################################################### 
# 
# 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_compound3e
_database_code_depnum_ccdc_archive 'CCDC 2193303'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.30

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'-x, -y, z+1/2'
'y, x, -z+1/3'
'-y, -x, -z+5/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/6'

_cell_length_a                   8.2970(4)
_cell_length_b                   8.2970(4)
_cell_length_c                   59.074(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3521.8(4)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6381
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      21.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50743
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -79
_diffrn_reflns_limit_l_max       79
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         28.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3063
_reflns_number_gt                2868
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.536
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1740P)²+8.6008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1516
_refine_ls_goodness_of_fit_ref   0.601
_refine_ls_restrained_S_all      0.601
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.13126(12) -0.07438(12) 0.94894(2) 0.0297(2) Uani 1 1 d . . . . .
O1 O 0.5929(3) 0.1874(4) 0.98031(4) 0.0333(6) Uani 1 1 d . . . . .
C1 C 0.3238(4) 0.3122(4) 0.99596(5) 0.0262(6) Uani 1 1 d . . . . .
H1 H 0.435534 0.375547 1.003839 0.031 Uiso 1 1 calc R U . . .
O2 O 0.4898(4) 0.0733(4) 0.91468(4) 0.0368(6) Uani 1 1 d . . . . .
N1 N 0.3528(4) -0.0144(4) 0.95719(4) 0.0282(6) Uani 1 1 d . . . . .
C2 C 0.2971(4) 0.1788(4) 0.97974(5) 0.0240(6) Uani 1 1 d . . . . .
C8 C 0.6364(6) -0.2666(6) 0.92917(6) 0.0364(8) Uani 1 1 d . . . . .
H8 H 0.702167 -0.320348 0.923175 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5605(6) -0.3159(6) 0.95085(6) 0.0370(8) Uani 1 1 d . . . . .
H9 H 0.573105 -0.404289 0.959129 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4664(5) -0.2328(5) 0.95999(6) 0.0324(7) Uani 1 1 d . . . . .
H10 H 0.417787 -0.263487 0.974548 0.039 Uiso 1 1 calc R U . . .
C11 C 0.4448(5) -0.1043(5) 0.94746(5) 0.0286(7) Uani 1 1 d . . . . .
C7 C 0.4338(4) 0.1239(5) 0.97330(5) 0.0249(6) Uani 1 1 d . . . . .
C3 C 0.1808(5) 0.3482(5) 1.00007(6) 0.0301(7) Uani 1 1 d . . . . .
H3 H 0.197223 0.438432 1.010612 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0117(5) 0.2500(5) 0.98850(6) 0.0306(7) Uani 1 1 d . . . . .
H4 H -0.083630 0.274887 0.991636 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1290(4) 0.0830(4) 0.96815(5) 0.0252(6) Uani 1 1 d . . . . .
C12 C 0.6145(6) -0.1377(6) 0.91647(6) 0.0337(7) Uani 1 1 d . . . . .
H12 H 0.664380 -0.106281 0.901973 0.040 Uiso 1 1 calc R U . . .
C13 C 0.5176(5) -0.0559(5) 0.92551(5) 0.0294(7) Uani 1 1 d . . . . .
C14 C 0.5714(6) 0.1324(7) 0.89266(6) 0.0432(9) Uani 1 1 d . . . . .
H14A H 0.703752 0.184589 0.893714 0.065 Uiso 1 1 calc R U . . .
H14B H 0.544475 0.224747 0.886946 0.065 Uiso 1 1 calc R U . . .
H14C H 0.520635 0.027588 0.882594 0.065 Uiso 1 1 calc R U . . .
C6 C -0.0166(5) 0.1166(5) 0.97249(5) 0.0290(7) Uani 1 1 d . . . . .
H6 H -0.129322 0.051447 0.964860 0.035 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 N1 1.718(3) . ?
S1 C5 1.737(3) . ?
O1 C7 1.223(4) . ?
C1 C3 1.382(5) . ?
C1 C2 1.395(4) . ?
C1 H1 0.9300 . ?
O2 C13 1.363(4) . ?
O2 C14 1.435(4) . ?
N1 C7 1.379(4) . ?
N1 C11 1.428(4) . ?
C2 C5 1.392(4) . ?
C2 C7 1.468(5) . ?
C8 C12 1.391(5) . ?
C8 C9 1.395(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(5) . ?
C10 H10 0.9300 . ?
C11 C13 1.401(4) . ?
C3 C4 1.399(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(5) . ?
C12 C13 1.392(5) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C6 H6 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
N1 S1 C5 90.51(15) . . ?
C3 C1 C2 118.6(3) . . ?
C3 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
C13 O2 C14 117.2(3) . . ?
C7 N1 C11 123.2(3) . . ?
C7 N1 S1 116.3(2) . . ?
C11 N1 S1 120.6(2) . . ?
C5 C2 C1 120.5(3) . . ?
C5 C2 C7 113.9(3) . . ?
C1 C2 C7 125.7(3) . . ?
C12 C8 C9 120.5(3) . . ?
C12 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C13 120.9(3) . . ?
C10 C11 N1 119.8(3) . . ?
C13 C11 N1 119.3(3) . . ?
O1 C7 N1 124.3(3) . . ?
O1 C7 C2 127.9(3) . . ?
N1 C7 C2 107.8(3) . . ?
C1 C3 C4 120.5(3) . . ?
C1 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C6 C4 C3 121.3(3) . . ?
C6 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C2 C5 C6 121.1(3) . . ?
C2 C5 S1 111.5(2) . . ?
C6 C5 S1 127.4(3) . . ?
C8 C12 C13 119.8(3) . . ?
C8 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
O2 C13 C12 124.7(3) . . ?
O2 C13 C11 116.2(3) . . ?
C12 C13 C11 119.1(3) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C6 C5 118.0(3) . . ?
C4 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.045


####################################################################### 
# 
# 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_compound3b
_database_code_depnum_ccdc_archive 'CCDC 2193301'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O S'
_chemical_formula_weight         241.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   9.6442(4)
_cell_length_b                   6.3275(2)
_cell_length_c                   19.5922(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.247(2)
_cell_angle_gamma                90
_cell_volume                     1188.49(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2745
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      27.81

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11850
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.140
_diffrn_reflns_theta_max         28.776
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3079
_reflns_number_gt                2222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3079
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   0.722
_refine_ls_restrained_S_all      0.722
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.57121(6) 0.38919(9) 0.58131(3) 0.0586(2) Uani 1 1 d . . . . .
C7 C 0.80986(18) 0.4083(3) 0.65830(8) 0.0407(4) Uani 1 1 d . . . . .
C1 C 0.59684(18) 0.5993(3) 0.63808(9) 0.0429(4) Uani 1 1 d . . . . .
C2 C 0.72784(18) 0.5922(3) 0.67531(8) 0.0389(4) Uani 1 1 d . . . . .
C9 C 0.80756(19) 0.1198(3) 0.50466(9) 0.0436(4) Uani 1 1 d . . . . .
C3 C 0.7687(2) 0.7502(3) 0.72244(9) 0.0486(5) Uani 1 1 d . . . . .
H3 H 0.857054 0.748483 0.746730 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7807(3) 0.1009(3) 0.57876(10) 0.0536(5) Uani 1 1 d . . . . .
H8A H 0.711452 -0.008471 0.582449 0.064 Uiso 1 1 calc R U . . .
H8B H 0.866132 0.056151 0.605580 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5034(2) 0.7611(4) 0.64816(12) 0.0561(5) Uani 1 1 d . . . . .
H4 H 0.415741 0.765769 0.623152 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6754(3) 0.9100(4) 0.73255(11) 0.0606(6) Uani 1 1 d . . . . .
H5 H 0.700925 1.016357 0.764209 0.073 Uiso 1 1 calc R U . . .
C10 C 0.8551(2) 0.3039(4) 0.47774(11) 0.0581(5) Uani 1 1 d . . . . .
H10 H 0.865671 0.424765 0.504838 0.070 Uiso 1 1 calc R U . . .
C6 C 0.5439(3) 0.9131(4) 0.69583(12) 0.0622(6) Uani 1 1 d . . . . .
H6 H 0.482043 1.020800 0.703817 0.075 Uiso 1 1 calc R U . . .
C12 C 0.8712(3) 0.1331(5) 0.37014(12) 0.0747(8) Uani 1 1 d . . . . .
H12 H 0.892880 0.137061 0.325057 0.090 Uiso 1 1 calc R U . . .
C14 C 0.7906(2) -0.0563(4) 0.46312(11) 0.0577(5) Uani 1 1 d . . . . .
H14 H 0.756967 -0.181034 0.480244 0.069 Uiso 1 1 calc R U . . .
C11 C 0.8872(2) 0.3102(5) 0.41034(13) 0.0710(7) Uani 1 1 d . . . . .
H11 H 0.919674 0.434733 0.392533 0.085 Uiso 1 1 calc R U . . .
C13 C 0.8233(3) -0.0487(5) 0.39630(13) 0.0757(8) Uani 1 1 d . . . . .
H13 H 0.812567 -0.168883 0.368925 0.091 Uiso 1 1 calc R U . . .
O1 O 0.92656(14) 0.3588(3) 0.68296(7) 0.0574(4) Uani 1 1 d . . . . .
N1 N 0.73266(17) 0.2943(3) 0.60824(8) 0.0477(4) 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
S1 N1 1.6984(16) . ?
S1 C1 1.734(2) . ?
C7 O1 1.216(2) . ?
C7 N1 1.370(2) . ?
C7 C2 1.465(3) . ?
C1 C2 1.389(2) . ?
C1 C4 1.393(3) . ?
C2 C3 1.389(3) . ?
C9 C10 1.378(3) . ?
C9 C14 1.379(3) . ?
C9 C8 1.507(3) . ?
C3 C5 1.382(3) . ?
C8 N1 1.450(3) . ?
C4 C6 1.367(3) . ?
C5 C6 1.389(4) . ?
C10 C11 1.389(3) . ?
C12 C13 1.360(4) . ?
C12 C11 1.369(4) . ?
C14 C13 1.381(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C1 90.57(8) . . ?
O1 C7 N1 123.77(18) . . ?
O1 C7 C2 127.81(18) . . ?
N1 C7 C2 108.42(15) . . ?
C2 C1 C4 121.01(19) . . ?
C2 C1 S1 111.71(14) . . ?
C4 C1 S1 127.27(16) . . ?
C3 C2 C1 120.11(18) . . ?
C3 C2 C7 127.00(17) . . ?
C1 C2 C7 112.89(16) . . ?
C10 C9 C14 118.71(19) . . ?
C10 C9 C8 122.32(18) . . ?
C14 C9 C8 118.89(18) . . ?
C5 C3 C2 118.71(19) . . ?
N1 C8 C9 114.38(16) . . ?
C6 C4 C1 118.2(2) . . ?
C3 C5 C6 120.5(2) . . ?
C9 C10 C11 120.4(2) . . ?
C4 C6 C5 121.4(2) . . ?
C13 C12 C11 119.8(2) . . ?
C9 C14 C13 120.5(2) . . ?
C12 C11 C10 120.1(2) . . ?
C12 C13 C14 120.6(2) . . ?
C7 N1 C8 123.84(17) . . ?
C7 N1 S1 116.40(13) . . ?
C8 N1 S1 119.76(14) . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.038


####################################################################### 
# 
# 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_compound3l
_database_code_depnum_ccdc_archive 'CCDC 2193306'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 N O3 S'
_chemical_formula_weight         223.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   14.9647(9)
_cell_length_b                   12.5644(8)
_cell_length_c                   10.6636(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.300(3)
_cell_angle_gamma                90
_cell_volume                     2001.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.85

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.308
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32183
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.801
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4750
_reflns_number_gt                4033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4750
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1424
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.240
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.13941(3) 0.08068(4) 1.10605(4) 0.03270(16) Uani 1 1 d . . . . .
S1 S 0.36452(3) 0.65045(4) 0.13969(5) 0.03896(17) Uani 1 1 d . . . . .
C17 C 0.06490(11) 0.10155(13) 0.87869(15) 0.0259(3) Uani 1 1 d . . . . .
C11 C 0.10277(11) -0.00604(13) 0.88754(15) 0.0256(3) Uani 1 1 d . . . . .
C12 C 0.14598(11) -0.02680(13) 1.00403(16) 0.0273(3) Uani 1 1 d . . . . .
C9 C 0.39345(12) 0.90147(15) 0.29743(17) 0.0320(4) Uani 1 1 d . . . . .
C19 C 0.11286(11) 0.34090(12) 0.96625(16) 0.0266(3) Uani 1 1 d . . . . .
C13 C 0.10082(12) -0.08250(14) 0.79275(17) 0.0327(4) Uani 1 1 d . . . . .
H13 H 0.070936 -0.068730 0.713394 0.039 Uiso 1 1 calc R U . . .
C18 C 0.04979(12) 0.25769(13) 1.01366(17) 0.0303(4) Uani 1 1 d . . . . .
H18A H 0.043809 0.268362 1.104782 0.036 Uiso 1 1 calc R U . . .
H18B H -0.010123 0.267239 0.970773 0.036 Uiso 1 1 calc R U . . .
C20 C 0.12225(12) 0.52609(13) 0.92403(18) 0.0337(4) Uani 1 1 d . . . . .
H20A H 0.141704 0.565722 0.999913 0.051 Uiso 1 1 calc R U . . .
H20B H 0.084685 0.571927 0.868471 0.051 Uiso 1 1 calc R U . . .
H20C H 0.174797 0.503174 0.880352 0.051 Uiso 1 1 calc R U . . .
C14 C 0.18943(12) -0.12368(15) 1.0285(2) 0.0370(4) Uani 1 1 d . . . . .
H14 H 0.218848 -0.138052 1.108068 0.044 Uiso 1 1 calc R U . . .
C1 C 0.34447(12) 0.53785(15) 0.2281(2) 0.0387(4) Uani 1 1 d . . . . .
C7 C 0.42201(14) 0.65002(15) 0.37617(18) 0.0376(4) Uani 1 1 d . . . . .
C2 C 0.37906(13) 0.54775(16) 0.3510(2) 0.0387(4) Uani 1 1 d . . . . .
C8 C 0.45690(12) 0.81396(15) 0.26284(17) 0.0325(4) Uani 1 1 d . . . . .
H8A H 0.475964 0.826955 0.176789 0.039 Uiso 1 1 calc R U . . .
H8B H 0.510939 0.816640 0.320844 0.039 Uiso 1 1 calc R U . . .
C15 C 0.18796(12) -0.19747(15) 0.9331(2) 0.0404(5) Uani 1 1 d . . . . .
H15 H 0.218280 -0.263256 0.946704 0.049 Uiso 1 1 calc R U . . .
C3 C 0.30063(14) 0.44471(18) 0.1871(3) 0.0516(6) Uani 1 1 d . . . . .
H3 H 0.277700 0.437095 0.102637 0.062 Uiso 1 1 calc R U . . .
C4 C 0.37055(17) 0.46427(17) 0.4367(2) 0.0507(6) Uani 1 1 d . . . . .
H4 H 0.394712 0.470615 0.520756 0.061 Uiso 1 1 calc R U . . .
C5 C 0.29186(15) 0.36403(17) 0.2740(3) 0.0601(8) Uani 1 1 d . . . . .
H5 H 0.261160 0.300750 0.248524 0.072 Uiso 1 1 calc R U . . .
C16 C 0.14301(13) -0.17831(15) 0.8163(2) 0.0399(4) Uani 1 1 d . . . . .
H16 H 0.141665 -0.231713 0.753185 0.048 Uiso 1 1 calc R U . . .
C6 C 0.32648(17) 0.37273(18) 0.3970(3) 0.0574(7) Uani 1 1 d . . . . .
H6 H 0.319850 0.315578 0.454066 0.069 Uiso 1 1 calc R U . . .
C10 C 0.38451(19) 1.0866(2) 0.3325(4) 0.0764(10) Uani 1 1 d . . . . .
H10A H 0.339551 1.099995 0.263832 0.115 Uiso 1 1 calc R U . . .
H10B H 0.424110 1.148467 0.342951 0.115 Uiso 1 1 calc R U . . .
H10C H 0.354529 1.074151 0.410488 0.115 Uiso 1 1 calc R U . . .
O4 O 0.02518(9) 0.14489(10) 0.78890(12) 0.0356(3) Uani 1 1 d . . . . .
O6 O 0.07143(8) 0.43378(10) 0.95850(14) 0.0354(3) Uani 1 1 d . . . . .
O2 O 0.31570(9) 0.89068(12) 0.31573(17) 0.0479(4) Uani 1 1 d . . . . .
O3 O 0.43686(10) 0.99351(12) 0.30318(18) 0.0531(4) Uani 1 1 d . . . . .
O5 O 0.18878(9) 0.32548(11) 0.94154(17) 0.0473(4) Uani 1 1 d . . . . .
O1 O 0.45884(13) 0.68273(14) 0.47427(13) 0.0567(5) Uani 1 1 d . . . . .
N2 N 0.08031(10) 0.15069(10) 0.99249(13) 0.0276(3) Uani 1 1 d . . . . .
N1 N 0.41794(11) 0.70917(12) 0.26800(14) 0.0327(3) 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
S2 N2 1.7027(15) . ?
S2 C12 1.7403(18) . ?
S1 N1 1.7116(16) . ?
S1 C1 1.736(2) . ?
C17 O4 1.225(2) . ?
C17 N2 1.369(2) . ?
C17 C11 1.467(2) . ?
C11 C12 1.392(2) . ?
C11 C13 1.394(2) . ?
C12 C14 1.398(2) . ?
C9 O2 1.198(2) . ?
C9 O3 1.326(2) . ?
C9 C8 1.512(2) . ?
C19 O5 1.197(2) . ?
C19 O6 1.322(2) . ?
C19 C18 1.515(2) . ?
C13 C16 1.376(3) . ?
C18 N2 1.442(2) . ?
C20 O6 1.446(2) . ?
C14 C15 1.376(3) . ?
C1 C2 1.386(3) . ?
C1 C3 1.399(3) . ?
C7 O1 1.225(3) . ?
C7 N1 1.371(2) . ?
C7 C2 1.455(3) . ?
C2 C4 1.402(3) . ?
C8 N1 1.442(2) . ?
C15 C16 1.402(3) . ?
C3 C5 1.385(4) . ?
C4 C6 1.380(4) . ?
C5 C6 1.387(4) . ?
C10 O3 1.452(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S2 C12 90.12(7) . . ?
N1 S1 C1 90.26(9) . . ?
O4 C17 N2 122.79(16) . . ?
O4 C17 C11 128.91(15) . . ?
N2 C17 C11 108.29(14) . . ?
C12 C11 C13 120.50(16) . . ?
C12 C11 C17 112.84(14) . . ?
C13 C11 C17 126.64(15) . . ?
C11 C12 C14 121.16(17) . . ?
C11 C12 S2 111.87(13) . . ?
C14 C12 S2 126.97(15) . . ?
O2 C9 O3 124.66(17) . . ?
O2 C9 C8 125.92(17) . . ?
O3 C9 C8 109.42(15) . . ?
O5 C19 O6 125.23(16) . . ?
O5 C19 C18 125.42(15) . . ?
O6 C19 C18 109.34(14) . . ?
C16 C13 C11 118.71(18) . . ?
N2 C18 C19 112.47(13) . . ?
C15 C14 C12 117.45(18) . . ?
C2 C1 C3 120.9(2) . . ?
C2 C1 S1 111.92(15) . . ?
C3 C1 S1 127.21(19) . . ?
O1 C7 N1 122.20(19) . . ?
O1 C7 C2 128.79(19) . . ?
N1 C7 C2 109.00(18) . . ?
C1 C2 C4 120.4(2) . . ?
C1 C2 C7 113.01(17) . . ?
C4 C2 C7 126.6(2) . . ?
N1 C8 C9 113.17(14) . . ?
C14 C15 C16 121.86(17) . . ?
C5 C3 C1 117.7(3) . . ?
C6 C4 C2 118.9(3) . . ?
C3 C5 C6 122.0(2) . . ?
C13 C16 C15 120.30(18) . . ?
C4 C6 C5 120.1(2) . . ?
C19 O6 C20 118.19(13) . . ?
C9 O3 C10 116.33(16) . . ?
C17 N2 C18 121.36(15) . . ?
C17 N2 S2 116.84(11) . . ?
C18 N2 S2 121.78(12) . . ?
C7 N1 C8 121.91(16) . . ?
C7 N1 S1 115.80(14) . . ?
C8 N1 S1 122.29(12) . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.052


####################################################################### 
# 
# 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_compound3d
_database_code_depnum_ccdc_archive 'CCDC 2193302'
loop_
_audit_author_name
_audit_author_address
'Chang-Chih Hsieh'
;Institute of Chemistry, Academia Sinica
Taiwan
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 N O2 S'
_chemical_formula_weight         243.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   8.2595(4)
_cell_length_b                   18.2546(8)
_cell_length_c                   7.3234(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.049(4)
_cell_angle_gamma                90
_cell_volume                     1079.85(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    875
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      18.46

_exptl_crystal_description       block
_exptl_crystal_colour            'light yelloiw'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6179
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.231
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2582
_reflns_number_gt                1784
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.964

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.87(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2582
_refine_ls_number_parameters     158
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_restrained_S_all      0.810
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.43616(16) 0.12992(6) 0.15329(17) 0.0478(4) Uani 1 1 d . . . . .
C8 C 0.1159(6) 0.1326(2) 0.1932(7) 0.0387(11) Uani 1 1 d . . . . .
C13 C 0.0292(6) 0.1660(2) 0.0311(7) 0.0396(11) Uani 1 1 d . . . . .
C7 C 0.2659(7) 0.0136(3) 0.2110(7) 0.0389(11) Uani 1 1 d . . . . .
C6 C 0.4283(6) -0.0115(2) 0.1865(7) 0.0350(10) Uani 1 1 d . . . . .
C1 C 0.5321(6) 0.0456(3) 0.1588(7) 0.0395(11) Uani 1 1 d . . . . .
C12 C -0.1019(7) 0.2121(3) 0.0436(8) 0.0496(13) Uani 1 1 d . . . . .
H12 H -0.159393 0.235878 -0.062737 0.059 Uiso 1 1 calc R U . . .
C11 C -0.1479(8) 0.2231(3) 0.2131(9) 0.0550(15) Uani 1 1 d . . . . .
H11 H -0.236496 0.253781 0.219427 0.066 Uiso 1 1 calc R U . . .
C3 C 0.7412(7) -0.0401(4) 0.1342(8) 0.0563(15) Uani 1 1 d . . . . .
H3 H 0.846900 -0.050631 0.115905 0.068 Uiso 1 1 calc R U . . .
C10 C -0.0630(7) 0.1887(3) 0.3728(8) 0.0519(14) Uani 1 1 d . . . . .
H10 H -0.095244 0.195715 0.485865 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4829(6) -0.0834(3) 0.1872(7) 0.0444(12) Uani 1 1 d . . . . .
H5 H 0.413922 -0.121762 0.205745 0.053 Uiso 1 1 calc R U . . .
C9 C 0.0696(7) 0.1440(3) 0.3639(8) 0.0466(12) Uani 1 1 d . . . . .
H9 H 0.128251 0.121420 0.471380 0.056 Uiso 1 1 calc R U . . .
C2 C 0.6929(7) 0.0306(3) 0.1343(8) 0.0512(14) Uani 1 1 d . . . . .
H2 H 0.764302 0.068412 0.118552 0.061 Uiso 1 1 calc R U . . .
C4 C 0.6388(7) -0.0974(3) 0.1603(8) 0.0535(14) Uani 1 1 d . . . . .
H4 H 0.676004 -0.145505 0.159486 0.064 Uiso 1 1 calc R U . . .
O1 O 0.1533(4) -0.02275(19) 0.2479(6) 0.0479(9) Uani 1 1 d . . . . .
O2 O 0.0667(5) 0.1562(2) -0.1381(5) 0.0522(10) Uani 1 1 d . . . . .
N1 N 0.2572(5) 0.0883(2) 0.1860(6) 0.0398(9) Uani 1 1 d . . . . .
H1 H 0.095(11) 0.113(5) -0.145(12) 0.11(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.722(4) . ?
S1 C1 1.728(5) . ?
C8 C13 1.393(7) . ?
C8 C9 1.396(7) . ?
C8 N1 1.430(6) . ?
C13 O2 1.350(6) . ?
C13 C12 1.390(7) . ?
C7 O1 1.218(6) . ?
C7 N1 1.376(6) . ?
C7 C6 1.463(7) . ?
C6 C5 1.388(7) . ?
C6 C1 1.391(6) . ?
C1 C2 1.404(8) . ?
C12 C11 1.386(8) . ?
C11 C10 1.383(9) . ?
C3 C2 1.352(8) . ?
C3 C4 1.384(9) . ?
C10 C9 1.379(8) . ?
C5 C4 1.367(7) . ?

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
N1 S1 C1 90.4(2) . . ?
C13 C8 C9 120.7(4) . . ?
C13 C8 N1 119.6(4) . . ?
C9 C8 N1 119.7(5) . . ?
O2 C13 C12 118.2(4) . . ?
O2 C13 C8 123.3(4) . . ?
C12 C13 C8 118.5(4) . . ?
O1 C7 N1 123.3(5) . . ?
O1 C7 C6 128.2(4) . . ?
N1 C7 C6 108.5(4) . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 C7 126.9(4) . . ?
C1 C6 C7 113.1(4) . . ?
C6 C1 C2 120.1(5) . . ?
C6 C1 S1 112.2(3) . . ?
C2 C1 S1 127.7(4) . . ?
C11 C12 C13 120.6(5) . . ?
C10 C11 C12 120.4(5) . . ?
C2 C3 C4 122.2(5) . . ?
C9 C10 C11 119.8(5) . . ?
C4 C5 C6 119.5(5) . . ?
C10 C9 C8 119.9(5) . . ?
C3 C2 C1 118.2(5) . . ?
C5 C4 C3 120.0(5) . . ?
C7 N1 C8 125.2(4) . . ?
C7 N1 S1 115.7(3) . . ?
C8 N1 S1 119.1(3) . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.045


