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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_structure2a-moca253
_database_code_depnum_ccdc_archive 'CCDC 2400597'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-22 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         'C9 H12 N2 O2 S'
_chemical_formula_sum            'C9 H12 N2 O2 S'
_chemical_formula_weight         212.27

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      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                   7.2268(4)
_cell_length_b                   7.9865(6)
_cell_length_c                   9.2053(8)
_cell_angle_alpha                103.537(7)
_cell_angle_beta                 92.512(6)
_cell_angle_gamma                108.209(6)
_cell_volume                     486.72(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2231
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.4590
_cell_measurement_theta_min      2.7380

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.307
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4769
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.781
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2232
_reflns_number_gt                1827
_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_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0340P)²+0.1911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         2232
_refine_ls_number_parameters     134
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.21160(6) 0.81331(6) 0.76729(5) 0.01452(15) Uani 1 1 d . . . . .
O1 O 0.31810(18) 0.95865(18) 0.89773(15) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.02272(18) 0.81532(19) 0.71199(16) 0.0207(3) Uani 1 1 d . . . . .
N1 N 0.6365(2) 0.8601(2) 0.76997(19) 0.0178(4) Uani 1 1 d D . . . .
H1A H 0.598(3) 0.896(3) 0.855(2) 0.021 Uiso 1 1 d D U . . .
H1B H 0.758(2) 0.861(3) 0.769(2) 0.021 Uiso 1 1 d D U . . .
N2 N 0.3334(2) 0.8028(2) 0.62462(18) 0.0157(4) Uani 1 1 d . . . . .
C1 C 0.5217(3) 0.8195(2) 0.6421(2) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.6184(3) 0.7925(3) 0.5012(2) 0.0206(5) Uani 1 1 d . . . . .
H2A H 0.716726 0.733207 0.515963 0.025 Uiso 1 1 calc R U . . .
H2B H 0.689714 0.913891 0.486355 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4801(3) 0.6792(3) 0.3595(2) 0.0285(5) Uani 1 1 d . . . . .
H3A H 0.555993 0.663061 0.274785 0.043 Uiso 1 1 calc R U . . .
H3B H 0.388888 0.741692 0.338576 0.043 Uiso 1 1 calc R U . . .
H3C H 0.405958 0.559566 0.373434 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1748(2) 0.6034(3) 0.8130(2) 0.0144(4) Uani 1 1 d . . . . .
C5 C 0.2627(3) 0.5998(3) 0.9491(2) 0.0174(4) Uani 1 1 d . . . . .
H5 H 0.345416 0.709507 1.017430 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2274(3) 0.4331(3) 0.9833(2) 0.0203(4) Uani 1 1 d . . . . .
H6 H 0.285147 0.428676 1.076469 0.024 Uiso 1 1 calc R U . . .
C7 C 0.1088(3) 0.2734(3) 0.8827(2) 0.0218(5) Uani 1 1 d . . . . .
H7 H 0.084690 0.159914 0.907097 0.026 Uiso 1 1 calc R U . . .
C8 C 0.0248(3) 0.2789(3) 0.7459(2) 0.0219(5) Uani 1 1 d . . . . .
H8 H -0.054697 0.168769 0.676334 0.026 Uiso 1 1 calc R U . . .
C9 C 0.0561(3) 0.4435(3) 0.7105(2) 0.0186(4) Uani 1 1 d . . . . .
H9 H -0.002517 0.447511 0.617567 0.022 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4420(13) . ?
S1 O1 1.4456(14) . ?
S1 N2 1.6133(16) . ?
S1 C4 1.766(2) . ?
N1 C1 1.322(2) . ?
N1 H1A 0.854(16) . ?
N1 H1B 0.879(15) . ?
N2 C1 1.324(2) . ?
C1 C2 1.503(3) . ?
C2 C3 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.390(3) . ?
C4 C9 1.392(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 116.46(8) . . ?
O2 S1 N2 105.93(8) . . ?
O1 S1 N2 113.17(8) . . ?
O2 S1 C4 107.69(8) . . ?
O1 S1 C4 108.01(9) . . ?
N2 S1 C4 104.86(9) . . ?
C1 N1 H1A 121.2(15) . . ?
C1 N1 H1B 120.3(15) . . ?
H1A N1 H1B 118(2) . . ?
C1 N2 S1 120.71(14) . . ?
N1 C1 N2 127.44(18) . . ?
N1 C1 C2 115.76(16) . . ?
N2 C1 C2 116.79(16) . . ?
C1 C2 C3 115.02(15) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 121.22(18) . . ?
C5 C4 S1 120.15(15) . . ?
C9 C4 S1 118.63(15) . . ?
C6 C5 C4 118.83(18) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C5 120.43(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.03(19) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.43(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 119.06(19) . . ?
C8 C9 H9 120.5 . . ?
C4 C9 H9 120.5 . . ?

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
O2 S1 N2 C1 172.39(14) . . . . ?
O1 S1 N2 C1 43.62(17) . . . . ?
C4 S1 N2 C1 -73.87(16) . . . . ?
S1 N2 C1 N1 -6.0(3) . . . . ?
S1 N2 C1 C2 175.13(14) . . . . ?
N1 C1 C2 C3 157.57(19) . . . . ?
N2 C1 C2 C3 -23.5(3) . . . . ?
O2 S1 C4 C5 -133.36(15) . . . . ?
O1 S1 C4 C5 -6.81(18) . . . . ?
N2 S1 C4 C5 114.14(16) . . . . ?
O2 S1 C4 C9 46.38(17) . . . . ?
O1 S1 C4 C9 172.93(14) . . . . ?
N2 S1 C4 C9 -66.12(16) . . . . ?
C9 C4 C5 C6 -1.2(3) . . . . ?
S1 C4 C5 C6 178.56(14) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 C4 0.7(3) . . . . ?
C5 C4 C9 C8 0.4(3) . . . . ?
S1 C4 C9 C8 -179.32(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.854(16) 2.26(2) 2.869(2) 128.0(18) . yes
N1 H1A O1 0.854(16) 2.261(18) 3.017(2) 147.6(19) 2_677 yes
N1 H1B O2 0.879(15) 2.119(17) 2.978(2) 165(2) 1_655 yes

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_structure2p-cua362
_database_code_depnum_ccdc_archive 'CCDC 2400602'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-22 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         'C16 H16 N2 O4 S'
_chemical_formula_sum            'C16 H16 N2 O4 S'
_chemical_formula_weight         332.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'-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                   7.62600(10)
_cell_length_b                   10.8033(2)
_cell_length_c                   36.3680(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2996.21(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6582
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.8270
_cell_measurement_theta_min      2.3600

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.131
_shelx_estimated_absorpt_T_min   0.361
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            11983
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         4.864
_diffrn_reflns_theta_max         70.064
_diffrn_reflns_theta_full        67.684
_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             2844
_reflns_number_gt                2464
_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       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0760P)²+1.7219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00204(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2844
_refine_ls_number_parameters     216
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.73011(7) 0.49864(4) 0.42033(2) 0.01593(19) Uani 1 1 d . . . . .
O1 O 0.8433(2) 0.39608(14) 0.42882(4) 0.0212(4) Uani 1 1 d . . . . .
O2 O 0.7893(2) 0.62050(14) 0.43036(4) 0.0241(4) Uani 1 1 d . . . . .
O3 O 0.5576(2) 0.62069(14) 0.19016(4) 0.0295(4) Uani 1 1 d . . . . .
O4 O 0.6431(2) 0.42407(13) 0.18054(4) 0.0215(4) Uani 1 1 d . . . . .
N1 N 0.6562(3) 0.29150(16) 0.36723(5) 0.0205(4) Uani 1 1 d D . . . .
H1A H 0.686(3) 0.266(2) 0.3891(4) 0.025 Uiso 1 1 d D U . . .
H1B H 0.634(3) 0.2312(17) 0.3518(6) 0.025 Uiso 1 1 d D U . . .
N2 N 0.6883(3) 0.50832(15) 0.37642(5) 0.0172(4) Uani 1 1 d . . . . .
C1 C 0.6601(3) 0.40861(18) 0.35642(5) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.6353(3) 0.43366(17) 0.31621(5) 0.0147(4) Uani 1 1 d . . . . .
C3 C 0.6960(3) 0.34911(18) 0.29014(6) 0.0169(4) Uani 1 1 d . . . . .
H3 H 0.745419 0.272743 0.297909 0.020 Uiso 1 1 calc R U . . .
C4 C 0.6845(3) 0.37611(18) 0.25291(6) 0.0171(4) Uani 1 1 d . . . . .
H4 H 0.727616 0.318812 0.235274 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6101(3) 0.48689(18) 0.24144(5) 0.0142(4) Uani 1 1 d . . . . .
C6 C 0.5480(3) 0.57125(18) 0.26743(6) 0.0173(4) Uani 1 1 d . . . . .
H6 H 0.496400 0.646838 0.259602 0.021 Uiso 1 1 calc R U . . .
C7 C 0.5613(3) 0.54497(18) 0.30463(5) 0.0162(4) Uani 1 1 d . . . . .
H7 H 0.520014 0.602951 0.322258 0.019 Uiso 1 1 calc R U . . .
C8 C 0.5990(3) 0.51963(18) 0.20165(6) 0.0176(4) Uani 1 1 d . . . . .
C9 C 0.6581(3) 0.4450(2) 0.14125(6) 0.0215(5) Uani 1 1 d . . . . .
H9A H 0.762597 0.496089 0.135741 0.026 Uiso 1 1 calc R U . . .
H9B H 0.552794 0.488339 0.131865 0.026 Uiso 1 1 calc R U . . .
C10 C 0.6747(3) 0.3197(2) 0.12379(6) 0.0258(5) Uani 1 1 d . . . . .
H10A H 0.696913 0.329294 0.097401 0.039 Uiso 1 1 calc R U . . .
H10B H 0.565710 0.273209 0.127432 0.039 Uiso 1 1 calc R U . . .
H10C H 0.772316 0.274715 0.135130 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5266(3) 0.47201(17) 0.44185(5) 0.0151(4) Uani 1 1 d . . . . .
C12 C 0.3911(3) 0.55729(19) 0.43788(6) 0.0220(5) Uani 1 1 d . . . . .
H12 H 0.408080 0.630630 0.423918 0.026 Uiso 1 1 calc R U . . .
C13 C 0.2313(3) 0.5339(2) 0.45452(7) 0.0260(5) Uani 1 1 d . . . . .
H13 H 0.136134 0.589497 0.451095 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2100(3) 0.4292(2) 0.47624(6) 0.0250(5) Uani 1 1 d . . . . .
H14 H 0.100494 0.414153 0.487875 0.030 Uiso 1 1 calc R U . . .
C15 C 0.3462(3) 0.3470(2) 0.48104(6) 0.0227(5) Uani 1 1 d . . . . .
H15 H 0.331500 0.277052 0.496554 0.027 Uiso 1 1 calc R U . . .
C16 C 0.5056(3) 0.36628(18) 0.46319(5) 0.0180(4) Uani 1 1 d . . . . .
H16 H 0.598362 0.308124 0.465558 0.022 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4381(15) . ?
S1 O2 1.4386(15) . ?
S1 N2 1.6319(18) . ?
S1 C11 1.762(2) . ?
O3 C8 1.211(3) . ?
O4 C8 1.330(2) . ?
O4 C9 1.451(2) . ?
N1 C1 1.325(3) . ?
N1 H1A 0.872(10) . ?
N1 H1B 0.877(10) . ?
N2 C1 1.317(3) . ?
C1 C2 1.499(3) . ?
C2 C7 1.393(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(3) . ?
C5 C8 1.492(3) . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.501(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.390(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 117.54(10) . . ?
O1 S1 N2 112.13(9) . . ?
O2 S1 N2 104.51(9) . . ?
O1 S1 C11 107.92(9) . . ?
O2 S1 C11 108.25(9) . . ?
N2 S1 C11 105.85(10) . . ?
C8 O4 C9 117.87(16) . . ?
C1 N1 H1A 124.7(18) . . ?
C1 N1 H1B 121.5(17) . . ?
H1A N1 H1B 113(2) . . ?
C1 N2 S1 121.31(14) . . ?
N2 C1 N1 128.36(19) . . ?
N2 C1 C2 114.30(17) . . ?
N1 C1 C2 117.31(17) . . ?
C7 C2 C3 119.58(18) . . ?
C7 C2 C1 120.12(17) . . ?
C3 C2 C1 120.18(17) . . ?
C4 C3 C2 120.29(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.00(19) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.87(19) . . ?
C4 C5 C8 121.25(18) . . ?
C6 C5 C8 118.86(17) . . ?
C7 C6 C5 120.15(19) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.10(19) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
O3 C8 O4 124.51(19) . . ?
O3 C8 C5 124.28(19) . . ?
O4 C8 C5 111.20(17) . . ?
O4 C9 C10 106.42(17) . . ?
O4 C9 H9A 110.4 . . ?
C10 C9 H9A 110.4 . . ?
O4 C9 H9B 110.4 . . ?
C10 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.1(2) . . ?
C16 C11 S1 118.91(16) . . ?
C12 C11 S1 119.99(16) . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 118.9(2) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?

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
O1 S1 N2 C1 39.7(2) . . . . ?
O2 S1 N2 C1 168.04(18) . . . . ?
C11 S1 N2 C1 -77.77(19) . . . . ?
S1 N2 C1 N1 1.7(3) . . . . ?
S1 N2 C1 C2 -176.25(14) . . . . ?
N2 C1 C2 C7 -30.5(3) . . . . ?
N1 C1 C2 C7 151.3(2) . . . . ?
N2 C1 C2 C3 145.5(2) . . . . ?
N1 C1 C2 C3 -32.7(3) . . . . ?
C7 C2 C3 C4 0.6(3) . . . . ?
C1 C2 C3 C4 -175.35(18) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C8 178.82(18) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C8 C5 C6 C7 -178.07(19) . . . . ?
C5 C6 C7 C2 -0.7(3) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 176.14(18) . . . . ?
C9 O4 C8 O3 5.8(3) . . . . ?
C9 O4 C8 C5 -173.20(17) . . . . ?
C4 C5 C8 O3 -169.7(2) . . . . ?
C6 C5 C8 O3 8.7(3) . . . . ?
C4 C5 C8 O4 9.3(3) . . . . ?
C6 C5 C8 O4 -172.26(19) . . . . ?
C8 O4 C9 C10 -169.54(19) . . . . ?
O1 S1 C11 C16 1.63(19) . . . . ?
O2 S1 C11 C16 -126.56(16) . . . . ?
N2 S1 C11 C16 121.85(16) . . . . ?
O1 S1 C11 C12 -179.51(16) . . . . ?
O2 S1 C11 C12 52.30(19) . . . . ?
N2 S1 C11 C12 -59.29(18) . . . . ?
C16 C11 C12 C13 -2.1(3) . . . . ?
S1 C11 C12 C13 179.03(17) . . . . ?
C11 C12 C13 C14 2.9(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 -2.0(3) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
S1 C11 C16 C15 178.22(16) . . . . ?
C14 C15 C16 C11 2.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.872(10) 2.35(2) 2.886(2) 120(2) . yes
N1 H1A O2 0.872(10) 2.180(15) 2.976(2) 152(2) 8_755 yes
N1 H1B O3 0.877(10) 2.426(15) 3.228(2) 152(2) 3_645 yes
C16 H16 O2 0.95 2.55 3.305(2) 137 8_755 yes

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_structure2j-moca251
_database_code_depnum_ccdc_archive 'CCDC 2400600'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-22 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         'C13 H11 Cl N2 O2 S'
_chemical_formula_sum            'C13 H11 Cl N2 O2 S'
_chemical_formula_weight         294.75

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'
Cl Cl 0.1484 0.1585 '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                   8.5033(3)
_cell_length_b                   23.1754(7)
_cell_length_c                   20.2967(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.005(3)
_cell_angle_gamma                90
_cell_volume                     3997.4(2)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    16625
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.3440
_cell_measurement_theta_min      2.6980

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.441
_shelx_estimated_absorpt_T_min   0.778
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            35775
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_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             9145
_reflns_number_gt                7577
_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_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0401P)²+1.8099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         9145
_refine_ls_number_parameters     532
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Cl1 Cl 1.03473(7) 1.06106(3) 0.30655(3) 0.04622(15) Uani 1 1 d . . . . .
S1 S 0.60058(5) 0.87213(2) 0.00654(2) 0.01676(9) Uani 1 1 d . . . . .
O1 O 0.62291(15) 0.81073(5) 0.01367(6) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.63346(14) 0.89684(5) -0.05666(5) 0.0230(3) Uani 1 1 d . . . . .
N1 N 0.68602(18) 0.83937(7) 0.14567(7) 0.0231(3) Uani 1 1 d D . . . .
H1A H 0.647(2) 0.8130(8) 0.1184(9) 0.028 Uiso 1 1 d D U . . .
H1B H 0.695(2) 0.8326(8) 0.1876(8) 0.028 Uiso 1 1 d D U . . .
N2 N 0.69909(16) 0.90933(6) 0.06085(6) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.72331(19) 0.89050(7) 0.12235(8) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.80310(19) 0.93224(7) 0.16810(8) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.7814(2) 0.99105(8) 0.15828(8) 0.0241(4) Uani 1 1 d . . . . .
H3 H 0.716384 1.004093 0.122293 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8534(2) 1.03093(8) 0.20025(9) 0.0287(4) Uani 1 1 d . . . . .
H4 H 0.838069 1.071108 0.193355 0.034 Uiso 1 1 calc R U . . .
C5 C 0.9482(2) 1.01126(8) 0.25248(9) 0.0279(4) Uani 1 1 d . . . . .
C6 C 0.9741(2) 0.95343(9) 0.26248(9) 0.0285(4) Uani 1 1 d . . . . .
H6 H 1.041187 0.940743 0.297978 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9015(2) 0.91362(8) 0.22037(8) 0.0244(4) Uani 1 1 d . . . . .
H7 H 0.918836 0.873530 0.227132 0.029 Uiso 1 1 calc R U . . .
C8 C 0.40277(19) 0.88781(7) 0.02313(7) 0.0179(3) Uani 1 1 d . . . . .
C9 C 0.3436(2) 0.94144(7) 0.00389(8) 0.0218(4) Uani 1 1 d . . . . .
H9 H 0.407882 0.968066 -0.018460 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1901(2) 0.95553(9) 0.01769(9) 0.0302(4) Uani 1 1 d . . . . .
H10 H 0.148585 0.992148 0.005219 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0971(2) 0.91611(10) 0.04974(9) 0.0340(5) Uani 1 1 d . . . . .
H11 H -0.008513 0.925775 0.058900 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1564(2) 0.86288(9) 0.06849(9) 0.0333(5) Uani 1 1 d . . . . .
H12 H 0.091386 0.836121 0.090244 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3109(2) 0.84831(8) 0.05565(8) 0.0247(4) Uani 1 1 d . . . . .
H13 H 0.352770 0.811950 0.068925 0.030 Uiso 1 1 calc R U . . .
Cl3 Cl 0.76545(8) 1.08956(2) 0.56206(2) 0.04200(14) Uani 1 1 d . . . . .
S3 S 0.75706(5) 0.78737(2) 0.34659(2) 0.01631(9) Uani 1 1 d . . . . .
O5 O 0.63692(14) 0.74734(5) 0.36608(6) 0.0217(3) Uani 1 1 d . . . . .
O6 O 0.76300(14) 0.80078(5) 0.27758(5) 0.0218(3) Uani 1 1 d . . . . .
N5 N 0.63964(19) 0.81123(6) 0.48041(7) 0.0238(3) Uani 1 1 d D . . . .
H5A H 0.629(2) 0.7773(7) 0.4631(9) 0.029 Uiso 1 1 d D U . . .
H5B H 0.610(2) 0.8158(9) 0.5205(8) 0.029 Uiso 1 1 d D U . . .
N6 N 0.75188(17) 0.84812(6) 0.38461(6) 0.0190(3) Uani 1 1 d . . . . .
C27 C 0.70011(19) 0.85288(7) 0.44515(8) 0.0163(3) Uani 1 1 d . . . . .
C28 C 0.71356(19) 0.91156(7) 0.47482(8) 0.0179(3) Uani 1 1 d . . . . .
C29 C 0.7864(2) 0.95518(7) 0.44011(8) 0.0251(4) Uani 1 1 d . . . . .
H29 H 0.825971 0.947130 0.397887 0.030 Uiso 1 1 calc R U . . .
C30 C 0.8022(2) 1.01019(8) 0.46613(9) 0.0297(4) Uani 1 1 d . . . . .
H30 H 0.851149 1.039929 0.442006 0.036 Uiso 1 1 calc R U . . .
C31 C 0.7454(2) 1.02098(7) 0.52776(9) 0.0258(4) Uani 1 1 d . . . . .
C32 C 0.6738(3) 0.97869(8) 0.56323(9) 0.0344(5) Uani 1 1 d . . . . .
H32 H 0.635783 0.986894 0.605684 0.041 Uiso 1 1 calc R U . . .
C33 C 0.6574(2) 0.92404(8) 0.53669(9) 0.0296(4) Uani 1 1 d . . . . .
H33 H 0.607264 0.894697 0.560985 0.035 Uiso 1 1 calc R U . . .
C34 C 0.9429(2) 0.75742(7) 0.36899(7) 0.0182(3) Uani 1 1 d . . . . .
C35 C 1.0778(2) 0.78957(8) 0.35845(8) 0.0236(4) Uani 1 1 d . . . . .
H35 H 1.069384 0.827719 0.341560 0.028 Uiso 1 1 calc R U . . .
C36 C 1.2244(2) 0.76575(9) 0.37268(9) 0.0302(4) Uani 1 1 d . . . . .
H36 H 1.317077 0.787697 0.366375 0.036 Uiso 1 1 calc R U . . .
C37 C 1.2351(2) 0.71001(9) 0.39605(9) 0.0345(5) Uani 1 1 d . . . . .
H37 H 1.335592 0.693479 0.405564 0.041 Uiso 1 1 calc R U . . .
C38 C 1.1013(3) 0.67806(9) 0.40571(10) 0.0357(5) Uani 1 1 d . . . . .
H38 H 1.110490 0.639536 0.421385 0.043 Uiso 1 1 calc R U . . .
C39 C 0.9525(2) 0.70161(8) 0.39275(9) 0.0272(4) Uani 1 1 d . . . . .
H39 H 0.860033 0.679845 0.400077 0.033 Uiso 1 1 calc R U . . .
Cl2 Cl 0.63296(6) 0.35562(2) 0.25744(2) 0.03298(12) Uani 1 1 d . . . . .
S2 S 0.44683(5) 0.69518(2) 0.17063(2) 0.01663(9) Uani 1 1 d . . . . .
O3 O 0.47095(15) 0.73359(5) 0.22576(6) 0.0261(3) Uani 1 1 d . . . . .
O4 O 0.53358(14) 0.70835(5) 0.11256(6) 0.0252(3) Uani 1 1 d . . . . .
N3 N 0.54294(19) 0.64081(6) 0.30155(7) 0.0234(3) Uani 1 1 d D . . . .
H3A H 0.539(2) 0.6784(7) 0.2990(10) 0.028 Uiso 1 1 d D U . . .
H3B H 0.565(2) 0.6242(8) 0.3400(8) 0.028 Uiso 1 1 d D U . . .
N4 N 0.47834(17) 0.62828(6) 0.18778(6) 0.0190(3) Uani 1 1 d . . . . .
C14 C 0.51763(19) 0.60960(7) 0.24757(8) 0.0164(3) Uani 1 1 d . . . . .
C15 C 0.53972(19) 0.54624(7) 0.25347(7) 0.0164(3) Uani 1 1 d . . . . .
C16 C 0.6405(2) 0.52264(7) 0.30178(8) 0.0213(4) Uani 1 1 d . . . . .
H16 H 0.691188 0.547111 0.333504 0.026 Uiso 1 1 calc R U . . .
C17 C 0.6674(2) 0.46387(7) 0.30390(9) 0.0235(4) Uani 1 1 d . . . . .
H17 H 0.736417 0.447777 0.336807 0.028 Uiso 1 1 calc R U . . .
C18 C 0.5923(2) 0.42872(7) 0.25743(8) 0.0212(4) Uani 1 1 d . . . . .
C19 C 0.4867(2) 0.45093(7) 0.21056(8) 0.0220(4) Uani 1 1 d . . . . .
H19 H 0.432603 0.426066 0.180241 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4612(2) 0.50969(7) 0.20851(8) 0.0194(3) Uani 1 1 d . . . . .
H20 H 0.389723 0.525438 0.176297 0.023 Uiso 1 1 calc R U . . .
C21 C 0.24592(19) 0.69809(7) 0.14652(8) 0.0176(3) Uani 1 1 d . . . . .
C22 C 0.1369(2) 0.71367(8) 0.19239(9) 0.0285(4) Uani 1 1 d . . . . .
H22 H 0.169504 0.721013 0.236851 0.034 Uiso 1 1 calc R U . . .
C23 C -0.0201(2) 0.71841(9) 0.17273(11) 0.0388(5) Uani 1 1 d . . . . .
H23 H -0.095971 0.728813 0.203858 0.047 Uiso 1 1 calc R U . . .
C24 C -0.0664(3) 0.70806(10) 0.10815(12) 0.0458(6) Uani 1 1 d . . . . .
H24 H -0.174111 0.711772 0.094830 0.055 Uiso 1 1 calc R U . . .
C25 C 0.0427(3) 0.69232(12) 0.06253(11) 0.0488(6) Uani 1 1 d . . . . .
H25 H 0.009757 0.684926 0.018130 0.059 Uiso 1 1 calc R U . . .
C26 C 0.1998(2) 0.68736(9) 0.08159(9) 0.0326(4) Uani 1 1 d . . . . .
H26 H 0.275399 0.676678 0.050433 0.039 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
Cl1 C5 1.7383(18) . ?
S1 O2 1.4411(11) . ?
S1 O1 1.4422(12) . ?
S1 N2 1.6110(14) . ?
S1 C8 1.7648(17) . ?
N1 C1 1.319(2) . ?
N1 H1A 0.879(15) . ?
N1 H1B 0.866(15) . ?
N2 C1 1.331(2) . ?
C1 C2 1.488(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.396(2) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(3) . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.386(2) . ?
C8 C9 1.392(2) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
Cl3 C31 1.7412(17) . ?
S3 O6 1.4374(11) . ?
S3 O5 1.4453(12) . ?
S3 N6 1.6069(14) . ?
S3 C34 1.7707(17) . ?
N5 C27 1.317(2) . ?
N5 H5A 0.864(15) . ?
N5 H5B 0.868(15) . ?
N6 C27 1.324(2) . ?
C27 C28 1.490(2) . ?
C28 C33 1.389(2) . ?
C28 C29 1.390(2) . ?
C29 C30 1.385(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.379(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.371(3) . ?
C32 C33 1.381(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C39 1.382(2) . ?
C34 C35 1.391(2) . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.378(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.377(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.395(3) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
Cl2 C18 1.7293(16) . ?
S2 O3 1.4388(12) . ?
S2 O4 1.4448(12) . ?
S2 N4 1.6093(14) . ?
S2 C21 1.7618(17) . ?
N3 C14 1.324(2) . ?
N3 H3A 0.872(15) . ?
N3 H3B 0.884(15) . ?
N4 C14 1.320(2) . ?
C14 C15 1.485(2) . ?
C15 C16 1.391(2) . ?
C15 C20 1.398(2) . ?
C16 C17 1.381(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(2) . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.384(2) . ?
C21 C22 1.384(2) . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 116.89(7) . . ?
O2 S1 N2 106.50(7) . . ?
O1 S1 N2 113.32(7) . . ?
O2 S1 C8 107.70(7) . . ?
O1 S1 C8 107.88(8) . . ?
N2 S1 C8 103.62(7) . . ?
C1 N1 H1A 119.1(13) . . ?
C1 N1 H1B 120.2(13) . . ?
H1A N1 H1B 120.6(19) . . ?
C1 N2 S1 121.72(12) . . ?
N1 C1 N2 126.85(15) . . ?
N1 C1 C2 118.04(14) . . ?
N2 C1 C2 115.11(14) . . ?
C3 C2 C7 119.03(16) . . ?
C3 C2 C1 119.53(15) . . ?
C7 C2 C1 121.43(16) . . ?
C4 C3 C2 120.87(16) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.92(18) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.36(17) . . ?
C6 C5 Cl1 119.53(14) . . ?
C4 C5 Cl1 119.11(15) . . ?
C5 C6 C7 119.51(17) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C2 120.29(17) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C13 C8 C9 121.31(16) . . ?
C13 C8 S1 120.77(14) . . ?
C9 C8 S1 117.90(13) . . ?
C10 C9 C8 119.23(16) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 119.84(18) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.61(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.26(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 118.75(17) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
O6 S3 O5 117.04(7) . . ?
O6 S3 N6 106.33(7) . . ?
O5 S3 N6 113.55(7) . . ?
O6 S3 C34 105.87(7) . . ?
O5 S3 C34 108.13(8) . . ?
N6 S3 C34 105.03(8) . . ?
C27 N5 H5A 118.8(14) . . ?
C27 N5 H5B 123.6(14) . . ?
H5A N5 H5B 117.5(19) . . ?
C27 N6 S3 122.29(12) . . ?
N5 C27 N6 126.30(15) . . ?
N5 C27 C28 118.38(15) . . ?
N6 C27 C28 115.33(14) . . ?
C33 C28 C29 118.67(15) . . ?
C33 C28 C27 122.10(15) . . ?
C29 C28 C27 119.22(15) . . ?
C30 C29 C28 121.00(16) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 118.72(17) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C32 C31 C30 121.50(16) . . ?
C32 C31 Cl3 118.80(14) . . ?
C30 C31 Cl3 119.70(14) . . ?
C31 C32 C33 119.41(17) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C32 C33 C28 120.69(17) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
C39 C34 C35 121.10(17) . . ?
C39 C34 S3 119.84(14) . . ?
C35 C34 S3 118.95(13) . . ?
C36 C35 C34 119.73(17) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 119.56(18) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C38 C37 C36 120.55(18) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C39 120.75(18) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C34 C39 C38 118.29(18) . . ?
C34 C39 H39 120.9 . . ?
C38 C39 H39 120.9 . . ?
O3 S2 O4 116.16(8) . . ?
O3 S2 N4 114.18(7) . . ?
O4 S2 N4 107.10(7) . . ?
O3 S2 C21 107.63(8) . . ?
O4 S2 C21 106.44(7) . . ?
N4 S2 C21 104.45(8) . . ?
C14 N3 H3A 119.4(13) . . ?
C14 N3 H3B 121.1(13) . . ?
H3A N3 H3B 119.6(18) . . ?
C14 N4 S2 123.34(11) . . ?
N4 C14 N3 127.58(15) . . ?
N4 C14 C15 115.20(13) . . ?
N3 C14 C15 117.20(14) . . ?
C16 C15 C20 119.36(15) . . ?
C16 C15 C14 121.24(14) . . ?
C20 C15 C14 119.37(14) . . ?
C17 C16 C15 120.43(15) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.13(16) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 121.45(15) . . ?
C19 C18 Cl2 119.30(13) . . ?
C17 C18 Cl2 119.25(13) . . ?
C20 C19 C18 119.03(15) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C15 120.51(16) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C26 C21 C22 120.88(17) . . ?
C26 C21 S2 119.81(13) . . ?
C22 C21 S2 119.25(13) . . ?
C21 C22 C23 119.23(18) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 120.11(19) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.5(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 119.9(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 119.34(18) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?

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
O2 S1 N2 C1 -164.75(13) . . . . ?
O1 S1 N2 C1 -34.86(16) . . . . ?
C8 S1 N2 C1 81.79(14) . . . . ?
S1 N2 C1 N1 6.5(2) . . . . ?
S1 N2 C1 C2 -174.41(12) . . . . ?
N1 C1 C2 C3 -150.63(17) . . . . ?
N2 C1 C2 C3 30.2(2) . . . . ?
N1 C1 C2 C7 30.3(2) . . . . ?
N2 C1 C2 C7 -148.84(16) . . . . ?
C7 C2 C3 C4 -1.3(3) . . . . ?
C1 C2 C3 C4 179.63(16) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C3 C4 C5 Cl1 -178.36(14) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
Cl1 C5 C6 C7 178.24(14) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C3 C2 C7 C6 1.2(3) . . . . ?
C1 C2 C7 C6 -179.77(16) . . . . ?
O2 S1 C8 C13 143.88(13) . . . . ?
O1 S1 C8 C13 16.88(15) . . . . ?
N2 S1 C8 C13 -103.53(14) . . . . ?
O2 S1 C8 C9 -37.56(15) . . . . ?
O1 S1 C8 C9 -164.56(12) . . . . ?
N2 S1 C8 C9 75.03(14) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
S1 C8 C9 C10 -178.42(13) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C9 C8 C13 C12 0.6(2) . . . . ?
S1 C8 C13 C12 179.08(13) . . . . ?
C11 C12 C13 C8 -0.8(3) . . . . ?
O6 S3 N6 C27 159.56(13) . . . . ?
O5 S3 N6 C27 29.43(16) . . . . ?
C34 S3 N6 C27 -88.50(15) . . . . ?
S3 N6 C27 N5 -3.9(2) . . . . ?
S3 N6 C27 C28 175.98(11) . . . . ?
N5 C27 C28 C33 -3.3(2) . . . . ?
N6 C27 C28 C33 176.84(16) . . . . ?
N5 C27 C28 C29 175.84(16) . . . . ?
N6 C27 C28 C29 -4.0(2) . . . . ?
C33 C28 C29 C30 -0.4(3) . . . . ?
C27 C28 C29 C30 -179.59(17) . . . . ?
C28 C29 C30 C31 0.6(3) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C29 C30 C31 Cl3 179.32(15) . . . . ?
C30 C31 C32 C33 -0.3(3) . . . . ?
Cl3 C31 C32 C33 -179.83(16) . . . . ?
C31 C32 C33 C28 0.4(3) . . . . ?
C29 C28 C33 C32 -0.1(3) . . . . ?
C27 C28 C33 C32 179.04(18) . . . . ?
O6 S3 C34 C39 -118.86(14) . . . . ?
O5 S3 C34 C39 7.32(16) . . . . ?
N6 S3 C34 C39 128.87(14) . . . . ?
O6 S3 C34 C35 57.25(14) . . . . ?
O5 S3 C34 C35 -176.57(12) . . . . ?
N6 S3 C34 C35 -55.02(14) . . . . ?
C39 C34 C35 C36 -0.8(3) . . . . ?
S3 C34 C35 C36 -176.87(13) . . . . ?
C34 C35 C36 C37 1.2(3) . . . . ?
C35 C36 C37 C38 -0.4(3) . . . . ?
C36 C37 C38 C39 -0.7(3) . . . . ?
C35 C34 C39 C38 -0.3(3) . . . . ?
S3 C34 C39 C38 175.74(14) . . . . ?
C37 C38 C39 C34 1.0(3) . . . . ?
O3 S2 N4 C14 2.24(17) . . . . ?
O4 S2 N4 C14 132.31(14) . . . . ?
C21 S2 N4 C14 -115.05(15) . . . . ?
S2 N4 C14 N3 -2.6(3) . . . . ?
S2 N4 C14 C15 179.28(12) . . . . ?
N4 C14 C15 C16 152.39(16) . . . . ?
N3 C14 C15 C16 -26.0(2) . . . . ?
N4 C14 C15 C20 -25.8(2) . . . . ?
N3 C14 C15 C20 155.84(16) . . . . ?
C20 C15 C16 C17 2.4(3) . . . . ?
C14 C15 C16 C17 -175.83(16) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 -2.4(3) . . . . ?
C16 C17 C18 Cl2 176.86(14) . . . . ?
C17 C18 C19 C20 2.8(3) . . . . ?
Cl2 C18 C19 C20 -176.49(13) . . . . ?
C18 C19 C20 C15 -0.6(3) . . . . ?
C16 C15 C20 C19 -2.0(2) . . . . ?
C14 C15 C20 C19 176.24(15) . . . . ?
O3 S2 C21 C26 151.82(15) . . . . ?
O4 S2 C21 C26 26.65(17) . . . . ?
N4 S2 C21 C26 -86.46(16) . . . . ?
O3 S2 C21 C22 -25.33(16) . . . . ?
O4 S2 C21 C22 -150.49(14) . . . . ?
N4 S2 C21 C22 96.39(15) . . . . ?
C26 C21 C22 C23 0.1(3) . . . . ?
S2 C21 C22 C23 177.20(15) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 0.2(4) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
S2 C21 C26 C25 -177.08(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.879(15) 2.130(18) 2.7939(19) 131.8(17) . yes
N1 H1B O6 0.866(15) 2.034(15) 2.8764(18) 163.8(19) . yes
N5 H5A O5 0.864(15) 2.092(18) 2.7521(18) 132.7(17) . yes
N5 H5B O4 0.868(15) 2.075(16) 2.8953(19) 157.4(19) 4_576 yes
N3 H3A O5 0.872(15) 2.241(18) 2.8941(18) 131.5(16) . yes
N3 H3A O3 0.872(15) 2.030(18) 2.7015(19) 133.0(17) . yes

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.452
_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_structure2e-moca254
_database_code_depnum_ccdc_archive 'CCDC 2400598'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-22 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         'C10 H12 N2 O2 S'
_chemical_formula_sum            'C10 H12 N2 O2 S'
_chemical_formula_weight         224.28

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                   8.4203(6)
_cell_length_b                   17.4676(10)
_cell_length_c                   7.2129(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.069(8)
_cell_angle_gamma                90
_cell_volume                     996.47(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3245
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.0880
_cell_measurement_theta_min      3.3820

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.305
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7114
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2291
_reflns_number_gt                1878
_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_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0437P)²+0.4859P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         2291
_refine_ls_number_parameters     142
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.32567(5) 0.63750(2) 0.86480(6) 0.01310(13) Uani 1 1 d . . . . .
O1 O 0.23162(16) 0.70591(7) 0.78088(18) 0.0187(3) Uani 1 1 d . . . . .
O2 O 0.31043(16) 0.61119(8) 1.04719(18) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.2535(2) 0.63814(9) 0.4311(2) 0.0172(3) Uani 1 1 d D . . . .
H1A H 0.253(3) 0.6810(10) 0.489(3) 0.021 Uiso 1 1 d D U . . .
H1B H 0.247(3) 0.6356(12) 0.309(2) 0.021 Uiso 1 1 d D U . . .
N2 N 0.28211(18) 0.56570(8) 0.7182(2) 0.0137(3) Uani 1 1 d . . . . .
C1 C 0.2607(2) 0.57336(10) 0.5280(2) 0.0126(3) Uani 1 1 d . . . . .
C2 C 0.2420(2) 0.50287(10) 0.4114(2) 0.0147(4) Uani 1 1 d . . . . .
H2 H 0.223191 0.509589 0.267754 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3387(2) 0.43216(10) 0.5080(3) 0.0170(4) Uani 1 1 d . . . . .
H3A H 0.380603 0.397848 0.425693 0.020 Uiso 1 1 calc R U . . .
H3B H 0.413692 0.436243 0.647548 0.020 Uiso 1 1 calc R U . . .
C4 C 0.1540(2) 0.43523(10) 0.4660(3) 0.0175(4) Uani 1 1 d . . . . .
H4A H 0.114064 0.441307 0.579227 0.021 Uiso 1 1 calc R U . . .
H4B H 0.080967 0.402903 0.357321 0.021 Uiso 1 1 calc R U . . .
C5 C 0.5416(2) 0.65642(10) 0.9077(2) 0.0132(3) Uani 1 1 d . . . . .
C6 C 0.6604(2) 0.59950(10) 0.9917(2) 0.0166(4) Uani 1 1 d . . . . .
H6 H 0.626417 0.551784 1.029168 0.020 Uiso 1 1 calc R U . . .
C7 C 0.8284(2) 0.61358(12) 1.0198(3) 0.0202(4) Uani 1 1 d . . . . .
H7 H 0.910601 0.575192 1.076813 0.024 Uiso 1 1 calc R U . . .
C8 C 0.8785(2) 0.68328(12) 0.9654(3) 0.0219(4) Uani 1 1 d . . . . .
H8 H 0.994375 0.692414 0.985283 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7596(2) 0.73936(11) 0.8823(3) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.794132 0.787015 0.845149 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5898(2) 0.72643(10) 0.8527(3) 0.0167(4) Uani 1 1 d . . . . .
H10 H 0.507924 0.764933 0.795725 0.020 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4403(13) . ?
S1 O1 1.4465(13) . ?
S1 N2 1.5999(14) . ?
S1 C5 1.7678(18) . ?
N1 C1 1.320(2) . ?
N1 H1A 0.859(15) . ?
N1 H1B 0.867(15) . ?
N2 C1 1.328(2) . ?
C1 C2 1.469(2) . ?
C2 C3 1.512(2) . ?
C2 C4 1.517(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.480(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.389(2) . ?
C5 C6 1.393(2) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 115.99(8) . . ?
O2 S1 N2 106.36(8) . . ?
O1 S1 N2 113.73(7) . . ?
O2 S1 C5 107.97(8) . . ?
O1 S1 C5 107.54(8) . . ?
N2 S1 C5 104.53(8) . . ?
C1 N1 H1A 119.7(14) . . ?
C1 N1 H1B 118.1(14) . . ?
H1A N1 H1B 122(2) . . ?
C1 N2 S1 121.54(12) . . ?
N1 C1 N2 126.76(16) . . ?
N1 C1 C2 116.05(15) . . ?
N2 C1 C2 117.19(15) . . ?
C1 C2 C3 119.08(14) . . ?
C1 C2 C4 118.08(15) . . ?
C3 C2 C4 58.53(11) . . ?
C1 C2 H2 116.3 . . ?
C3 C2 H2 116.3 . . ?
C4 C2 H2 116.3 . . ?
C4 C3 C2 60.91(12) . . ?
C4 C3 H3A 117.7 . . ?
C2 C3 H3A 117.7 . . ?
C4 C3 H3B 117.7 . . ?
C2 C3 H3B 117.7 . . ?
H3A C3 H3B 114.8 . . ?
C3 C4 C2 60.56(11) . . ?
C3 C4 H4A 117.7 . . ?
C2 C4 H4A 117.7 . . ?
C3 C4 H4B 117.7 . . ?
C2 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
C10 C5 C6 121.08(16) . . ?
C10 C5 S1 119.91(14) . . ?
C6 C5 S1 118.99(14) . . ?
C7 C6 C5 118.89(17) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 120.67(18) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.97(17) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.34(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C5 C10 C9 119.05(17) . . ?
C5 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?

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
O2 S1 N2 C1 170.13(13) . . . . ?
O1 S1 N2 C1 41.24(16) . . . . ?
C5 S1 N2 C1 -75.77(15) . . . . ?
S1 N2 C1 N1 -7.8(3) . . . . ?
S1 N2 C1 C2 172.64(12) . . . . ?
N1 C1 C2 C3 145.96(16) . . . . ?
N2 C1 C2 C3 -34.4(2) . . . . ?
N1 C1 C2 C4 -146.40(16) . . . . ?
N2 C1 C2 C4 33.2(2) . . . . ?
C1 C2 C3 C4 106.92(17) . . . . ?
C1 C2 C4 C3 -108.63(17) . . . . ?
O2 S1 C5 C10 -128.60(14) . . . . ?
O1 S1 C5 C10 -2.76(16) . . . . ?
N2 S1 C5 C10 118.45(14) . . . . ?
O2 S1 C5 C6 53.15(15) . . . . ?
O1 S1 C5 C6 179.00(13) . . . . ?
N2 S1 C5 C6 -59.80(15) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
S1 C5 C6 C7 178.11(13) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
S1 C5 C10 C9 -178.09(13) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.859(15) 2.215(19) 2.850(2) 130.6(18) . yes
N1 H1B O2 0.867(15) 2.172(16) 3.005(2) 161.1(19) 1_554 yes

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_structure2u-cua363
_database_code_depnum_ccdc_archive 'CCDC 2400603'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-22 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         'C11 H10 N2 O2 S2'
_chemical_formula_sum            'C11 H10 N2 O2 S2'
_chemical_formula_weight         266.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.5242(2)
_cell_length_b                   9.8469(2)
_cell_length_c                   10.7702(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.211(2)
_cell_angle_gamma                90
_cell_volume                     1209.65(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6076
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.8860
_cell_measurement_theta_min      4.1290

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.932
_shelx_estimated_absorpt_T_min   0.385
_shelx_estimated_absorpt_T_max   0.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            8114
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.875
_diffrn_reflns_theta_max         70.049
_diffrn_reflns_theta_full        67.684
_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             2295
_reflns_number_gt                2082
_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       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0595P)²+0.7499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         2295
_refine_ls_number_parameters     160
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.80532(4) 0.08834(5) 0.41177(4) 0.01796(15) Uani 1 1 d . . . . .
S2 S 0.83719(5) 0.68840(5) 0.52779(4) 0.02584(16) Uani 1 1 d . . . . .
O1 O 0.85066(13) 0.03512(15) 0.30286(12) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.83353(12) 0.01084(14) 0.52614(12) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.86181(17) 0.30750(18) 0.23867(15) 0.0239(4) Uani 1 1 d D . . . .
H1A H 0.869(2) 0.2241(13) 0.214(2) 0.029 Uiso 1 1 d D U . . .
H1B H 0.866(2) 0.3741(19) 0.1847(18) 0.029 Uiso 1 1 d D U . . .
N2 N 0.84076(14) 0.24242(17) 0.44612(13) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.85379(16) 0.3338(2) 0.35801(17) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.85910(16) 0.4760(2) 0.39717(16) 0.0171(4) Uani 1 1 d . . . . .
C3 C 0.89643(17) 0.5878(2) 0.32771(18) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.924049 0.578243 0.249169 0.025 Uiso 1 1 calc R U . . .
C4 C 0.88803(16) 0.7102(2) 0.38673(17) 0.0201(4) Uani 1 1 d . . . . .
H4 H 0.907682 0.795398 0.354011 0.024 Uiso 1 1 calc R U . . .
C5 C 0.82524(17) 0.5177(2) 0.50790(18) 0.0216(4) Uani 1 1 d . . . . .
H5 H 0.798184 0.457890 0.566798 0.026 Uiso 1 1 calc R U . . .
C6 C 0.65057(19) 0.0949(2) 0.3751(2) 0.0275(5) Uani 1 1 d . . . . .
C7 C 0.5874(2) 0.1634(3) 0.4566(3) 0.0434(6) Uani 1 1 d . . . . .
H7 H 0.627104 0.206041 0.529650 0.052 Uiso 1 1 calc R U . . .
C8 C 0.4666(3) 0.1690(4) 0.4304(4) 0.0636(9) Uani 1 1 d . . . . .
H8 H 0.422854 0.214596 0.486136 0.076 Uiso 1 1 calc R U . . .
C9 C 0.4100(3) 0.1086(4) 0.3240(4) 0.0747(12) Uani 1 1 d . . . . .
H9 H 0.326961 0.113772 0.305649 0.090 Uiso 1 1 calc R U . . .
C10 C 0.4718(3) 0.0411(5) 0.2442(3) 0.0834(14) Uani 1 1 d . . . . .
H10 H 0.431281 0.000056 0.170750 0.100 Uiso 1 1 calc R U . . .
C11 C 0.5949(3) 0.0314(4) 0.2692(3) 0.0563(9) Uani 1 1 d . . . . .
H11 H 0.638045 -0.017247 0.214813 0.068 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4460(14) . ?
S1 O1 1.4486(13) . ?
S1 N2 1.6008(17) . ?
S1 C6 1.772(2) . ?
S2 C5 1.698(2) . ?
S2 C4 1.7180(19) . ?
N1 C1 1.327(2) . ?
N1 H1A 0.870(10) . ?
N1 H1B 0.882(10) . ?
N2 C1 1.332(2) . ?
C1 C2 1.461(3) . ?
C2 C5 1.369(3) . ?
C2 C3 1.431(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C11 1.377(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.381(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.365(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.409(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 115.83(9) . . ?
O2 S1 N2 106.52(8) . . ?
O1 S1 N2 114.86(8) . . ?
O2 S1 C6 107.79(9) . . ?
O1 S1 C6 107.51(10) . . ?
N2 S1 C6 103.44(10) . . ?
C5 S2 C4 92.51(10) . . ?
C1 N1 H1A 120.0(16) . . ?
C1 N1 H1B 120.7(16) . . ?
H1A N1 H1B 119(2) . . ?
C1 N2 S1 121.78(13) . . ?
N1 C1 N2 126.08(19) . . ?
N1 C1 C2 117.42(17) . . ?
N2 C1 C2 116.50(16) . . ?
C5 C2 C3 111.68(18) . . ?
C5 C2 C1 122.20(17) . . ?
C3 C2 C1 126.11(16) . . ?
C4 C3 C2 112.76(17) . . ?
C4 C3 H3 123.6 . . ?
C2 C3 H3 123.6 . . ?
C3 C4 S2 110.82(15) . . ?
C3 C4 H4 124.6 . . ?
S2 C4 H4 124.6 . . ?
C2 C5 S2 112.22(15) . . ?
C2 C5 H5 123.9 . . ?
S2 C5 H5 123.9 . . ?
C11 C6 C7 121.3(2) . . ?
C11 C6 S1 120.2(2) . . ?
C7 C6 S1 118.55(18) . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C6 C11 C10 117.7(3) . . ?
C6 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C1 162.99(15) . . . . ?
O1 S1 N2 C1 33.33(18) . . . . ?
C6 S1 N2 C1 -83.52(16) . . . . ?
S1 N2 C1 N1 -13.5(3) . . . . ?
S1 N2 C1 C2 166.20(13) . . . . ?
N1 C1 C2 C5 164.62(18) . . . . ?
N2 C1 C2 C5 -15.1(3) . . . . ?
N1 C1 C2 C3 -14.1(3) . . . . ?
N2 C1 C2 C3 166.20(18) . . . . ?
C5 C2 C3 C4 -0.9(2) . . . . ?
C1 C2 C3 C4 177.88(17) . . . . ?
C2 C3 C4 S2 1.1(2) . . . . ?
C5 S2 C4 C3 -0.72(16) . . . . ?
C3 C2 C5 S2 0.4(2) . . . . ?
C1 C2 C5 S2 -178.49(14) . . . . ?
C4 S2 C5 C2 0.19(16) . . . . ?
O2 S1 C6 C11 -114.0(2) . . . . ?
O1 S1 C6 C11 11.6(2) . . . . ?
N2 S1 C6 C11 133.5(2) . . . . ?
O2 S1 C6 C7 65.0(2) . . . . ?
O1 S1 C6 C7 -169.43(19) . . . . ?
N2 S1 C6 C7 -47.5(2) . . . . ?
C11 C6 C7 C8 -0.5(4) . . . . ?
S1 C6 C7 C8 -179.5(2) . . . . ?
C6 C7 C8 C9 -0.8(5) . . . . ?
C7 C8 C9 C10 0.9(6) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C7 C6 C11 C10 1.6(5) . . . . ?
S1 C6 C11 C10 -179.4(3) . . . . ?
C9 C10 C11 C6 -1.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.870(10) 2.115(19) 2.777(2) 132(2) . yes
N1 H1B O2 0.882(10) 2.039(12) 2.887(2) 161(2) 4_565 yes
C4 H4 O1 0.95 2.49 3.336(3) 148 1_565 yes
C5 H5 O1 0.95 2.53 3.191(2) 127 4_566 yes

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_structure2y-cua388
_database_code_depnum_ccdc_archive 'CCDC 2400604'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-22 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         'C15 H16 N2 O3 S'
_chemical_formula_sum            'C15 H16 N2 O3 S'
_chemical_formula_weight         304.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.8160(2)
_cell_length_b                   5.54900(10)
_cell_length_c                   16.7197(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.198(2)
_cell_angle_gamma                90
_cell_volume                     719.43(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6023
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.2050
_cell_measurement_theta_min      5.3020

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.109
_shelx_estimated_absorpt_T_min   0.364
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            7568
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         70.072
_diffrn_reflns_theta_full        67.684
_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 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.873
_reflns_number_total             2399
_reflns_number_gt                2301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_max     0.708
_reflns_Friedel_fraction_full    0.715

_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       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0689P)²+0.1074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.059(17)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2399
_refine_ls_number_parameters     198
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.14823(9) 0.58823(14) 0.78926(4) 0.0219(2) Uani 1 1 d . . . . .
O1 O 0.0191(3) 0.4149(4) 0.80569(13) 0.0268(5) Uani 1 1 d . . . . .
O2 O 0.1192(3) 0.8348(4) 0.81060(14) 0.0296(6) Uani 1 1 d . . . . .
O3 O 0.2982(4) 0.4528(5) 0.32982(14) 0.0376(7) Uani 1 1 d . . . . .
N1 N 0.1537(4) 0.1669(5) 0.68305(17) 0.0277(7) Uani 1 1 d D . . . .
H1A H 0.121(5) 0.135(8) 0.7301(12) 0.033 Uiso 1 1 d D U . . .
H1B H 0.172(5) 0.033(4) 0.657(2) 0.033 Uiso 1 1 d D U . . .
N2 N 0.1776(3) 0.5893(6) 0.69459(13) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.1816(4) 0.3831(6) 0.65495(19) 0.0207(6) Uani 1 1 d . . . . .
C2 C 0.2189(4) 0.4006(6) 0.57005(17) 0.0199(6) Uani 1 1 d . . . . .
C3 C 0.1617(4) 0.2241(6) 0.51321(19) 0.0241(7) Uani 1 1 d . . . . .
H3 H 0.102243 0.086579 0.529348 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1909(4) 0.2480(7) 0.43388(19) 0.0270(7) Uani 1 1 d . . . . .
H4 H 0.150930 0.127005 0.395854 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2782(4) 0.4473(7) 0.40910(18) 0.0251(7) Uani 1 1 d . . . . .
C6 C 0.3390(4) 0.6234(6) 0.46510(18) 0.0246(7) Uani 1 1 d . . . . .
H6 H 0.400181 0.759321 0.448949 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3088(4) 0.5974(7) 0.54512(17) 0.0227(6) Uani 1 1 d . . . . .
H7 H 0.350474 0.716739 0.583414 0.027 Uiso 1 1 calc R U . . .
C8 C 0.3508(5) 0.6728(8) 0.2965(2) 0.0355(9) Uani 1 1 d . . . . .
H8A H 0.353400 0.652729 0.238428 0.053 Uiso 1 1 calc R U . . .
H8B H 0.466105 0.716310 0.322385 0.053 Uiso 1 1 calc R U . . .
H8C H 0.269066 0.800691 0.305739 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3484(4) 0.4950(6) 0.84082(18) 0.0219(7) Uani 1 1 d . . . . .
C10 C 0.3579(4) 0.2840(6) 0.88597(18) 0.0245(7) Uani 1 1 d . . . . .
H10 H 0.257532 0.189927 0.889444 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5166(4) 0.2129(7) 0.92596(19) 0.0280(7) Uani 1 1 d . . . . .
H11 H 0.523840 0.069210 0.957096 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6645(4) 0.3478(7) 0.92127(19) 0.0276(7) Uani 1 1 d . . . . .
C13 C 0.6517(4) 0.5594(8) 0.87525(19) 0.0304(8) Uani 1 1 d . . . . .
H13 H 0.751932 0.653407 0.871419 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4948(4) 0.6331(6) 0.83535(19) 0.0272(7) Uani 1 1 d . . . . .
H14 H 0.487172 0.777196 0.804404 0.033 Uiso 1 1 calc R U . . .
C15 C 0.8349(5) 0.2687(8) 0.9654(2) 0.0395(9) Uani 1 1 d . . . . .
H15A H 0.843017 0.320243 1.021816 0.059 Uiso 1 1 calc R U . . .
H15B H 0.928919 0.341683 0.940109 0.059 Uiso 1 1 calc R U . . .
H15C H 0.843804 0.092767 0.963026 0.059 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.439(3) . ?
S1 O1 1.445(2) . ?
S1 N2 1.628(2) . ?
S1 C9 1.766(3) . ?
O3 C5 1.354(4) . ?
O3 C8 1.424(5) . ?
N1 C1 1.316(4) . ?
N1 H1A 0.873(13) . ?
N1 H1B 0.877(13) . ?
N2 C1 1.325(4) . ?
C1 C2 1.488(4) . ?
C2 C7 1.390(5) . ?
C2 C3 1.399(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(5) . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.390(4) . ?
C9 C14 1.390(5) . ?
C10 C11 1.391(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(5) . ?
C12 C15 1.505(5) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 116.75(15) . . ?
O2 S1 N2 106.48(15) . . ?
O1 S1 N2 111.98(14) . . ?
O2 S1 C9 108.36(15) . . ?
O1 S1 C9 108.00(15) . . ?
N2 S1 C9 104.56(14) . . ?
C5 O3 C8 118.5(3) . . ?
C1 N1 H1A 126(3) . . ?
C1 N1 H1B 123(3) . . ?
H1A N1 H1B 111(4) . . ?
C1 N2 S1 119.9(2) . . ?
N1 C1 N2 126.4(3) . . ?
N1 C1 C2 117.5(3) . . ?
N2 C1 C2 116.1(3) . . ?
C7 C2 C3 118.5(3) . . ?
C7 C2 C1 120.3(3) . . ?
C3 C2 C1 121.2(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
O3 C5 C4 115.5(3) . . ?
O3 C5 C6 124.7(3) . . ?
C4 C5 C6 119.8(3) . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C2 C7 C6 121.4(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 120.8(3) . . ?
C10 C9 S1 119.7(3) . . ?
C14 C9 S1 119.5(3) . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 C15 120.5(3) . . ?
C13 C12 C15 120.8(3) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 119.5(3) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O2 S1 N2 C1 -169.8(2) . . . . ?
O1 S1 N2 C1 -41.1(3) . . . . ?
C9 S1 N2 C1 75.6(3) . . . . ?
S1 N2 C1 N1 4.2(4) . . . . ?
S1 N2 C1 C2 -176.7(2) . . . . ?
N1 C1 C2 C7 -156.5(3) . . . . ?
N2 C1 C2 C7 24.3(4) . . . . ?
N1 C1 C2 C3 25.0(4) . . . . ?
N2 C1 C2 C3 -154.2(3) . . . . ?
C7 C2 C3 C4 -1.3(5) . . . . ?
C1 C2 C3 C4 177.2(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C8 O3 C5 C4 166.2(3) . . . . ?
C8 O3 C5 C6 -14.2(5) . . . . ?
C3 C4 C5 O3 -179.5(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
O3 C5 C6 C7 179.5(3) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C3 C2 C7 C6 1.4(5) . . . . ?
C1 C2 C7 C6 -177.2(3) . . . . ?
C5 C6 C7 C2 -0.3(5) . . . . ?
O2 S1 C9 C10 128.2(3) . . . . ?
O1 S1 C9 C10 0.8(3) . . . . ?
N2 S1 C9 C10 -118.6(3) . . . . ?
O2 S1 C9 C14 -52.2(3) . . . . ?
O1 S1 C9 C14 -179.5(2) . . . . ?
N2 S1 C9 C14 61.1(3) . . . . ?
C14 C9 C10 C11 0.2(5) . . . . ?
S1 C9 C10 C11 179.8(2) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C10 C11 C12 C15 179.6(3) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C15 C12 C13 C14 -179.4(3) . . . . ?
C12 C13 C14 C9 -0.2(5) . . . . ?
C10 C9 C14 C13 0.1(5) . . . . ?
S1 C9 C14 C13 -179.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.873(13) 2.21(4) 2.783(4) 123(4) . yes
N1 H1A O2 0.873(13) 2.15(3) 2.857(4) 138(4) 1_545 yes
N1 H1B N2 0.877(13) 2.54(3) 3.215(4) 134(3) 1_545 yes
C10 H10 O2 0.95 2.54 3.270(4) 134 1_545 yes
C15 H15B O1 0.98 2.47 3.290(4) 141 1_655 yes

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.564
_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_structure2m-cua387
_database_code_depnum_ccdc_archive 'CCDC 2400601'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-22 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         'C14 H14 N2 O3 S'
_chemical_formula_sum            'C14 H14 N2 O3 S'
_chemical_formula_weight         290.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'-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                   14.3193(2)
_cell_length_b                   7.07640(10)
_cell_length_c                   27.0199(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2737.90(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7464
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.3610
_cell_measurement_theta_min      3.2160

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.190
_shelx_estimated_absorpt_T_min   0.353
_shelx_estimated_absorpt_T_max   0.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_reflns_number            13827
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.271
_diffrn_reflns_theta_max         70.074
_diffrn_reflns_theta_full        67.684
_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             2602
_reflns_number_gt                2271
_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       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0651P)²+0.8878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2602
_refine_ls_number_parameters     189
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_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 0.62261(3) -0.03928(5) 0.66922(2) 0.01885(17) Uani 1 1 d . . . . .
O1 O 0.66683(9) 0.05847(17) 0.71000(4) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.65468(9) -0.22872(17) 0.65954(5) 0.0265(3) Uani 1 1 d . . . . .
O3 O 0.61881(11) 0.5424(2) 0.41969(5) 0.0385(4) Uani 1 1 d . . . . .
N1 N 0.62923(11) 0.3740(2) 0.65283(5) 0.0241(3) Uani 1 1 d D . . . .
H1A H 0.6407(15) 0.326(3) 0.6822(5) 0.029 Uiso 1 1 d D U . . .
H1B H 0.6354(15) 0.4960(15) 0.6485(9) 0.029 Uiso 1 1 d D U . . .
N2 N 0.62803(10) 0.0702(2) 0.61720(5) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.62869(11) 0.2573(2) 0.61460(6) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.62754(11) 0.3389(2) 0.56397(6) 0.0209(4) Uani 1 1 d . . . . .
C3 C 0.65076(14) 0.5263(3) 0.55486(7) 0.0267(4) Uani 1 1 d . . . . .
H3 H 0.668114 0.605492 0.581717 0.032 Uiso 1 1 calc R U . . .
C4 C 0.64909(14) 0.6003(3) 0.50705(7) 0.0290(4) Uani 1 1 d . . . . .
H4 H 0.665406 0.728581 0.501339 0.035 Uiso 1 1 calc R U . . .
C5 C 0.62334(13) 0.4846(3) 0.46789(7) 0.0279(4) Uani 1 1 d . . . . .
C6 C 0.60128(16) 0.2961(3) 0.47642(7) 0.0343(5) Uani 1 1 d . . . . .
H6 H 0.584286 0.216813 0.449504 0.041 Uiso 1 1 calc R U . . .
C7 C 0.60398(14) 0.2235(3) 0.52383(7) 0.0283(4) Uani 1 1 d . . . . .
H7 H 0.589715 0.094030 0.529242 0.034 Uiso 1 1 calc R U . . .
C8 C 0.63217(16) 0.7382(3) 0.40981(8) 0.0396(5) Uani 1 1 d . . . . .
H8A H 0.623295 0.762065 0.374394 0.059 Uiso 1 1 calc R U . . .
H8B H 0.695610 0.774983 0.419425 0.059 Uiso 1 1 calc R U . . .
H8C H 0.586812 0.812286 0.428811 0.059 Uiso 1 1 calc R U . . .
C9 C 0.50228(12) -0.0552(2) 0.68289(6) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.44861(13) -0.1910(2) 0.65863(6) 0.0238(4) Uani 1 1 d . . . . .
H10 H 0.476469 -0.273286 0.635097 0.029 Uiso 1 1 calc R U . . .
C11 C 0.35433(14) -0.2045(3) 0.66919(7) 0.0295(4) Uani 1 1 d . . . . .
H11 H 0.317107 -0.296594 0.652895 0.035 Uiso 1 1 calc R U . . .
C12 C 0.31400(14) -0.0836(3) 0.70359(7) 0.0303(4) Uani 1 1 d . . . . .
H12 H 0.249109 -0.092763 0.710500 0.036 Uiso 1 1 calc R U . . .
C13 C 0.36771(14) 0.0501(3) 0.72790(7) 0.0286(4) Uani 1 1 d . . . . .
H13 H 0.339673 0.131207 0.751656 0.034 Uiso 1 1 calc R U . . .
C14 C 0.46261(13) 0.0660(2) 0.71764(6) 0.0240(4) Uani 1 1 d . . . . .
H14 H 0.499712 0.157924 0.734048 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 O2 1.4409(13) . ?
S1 O1 1.4469(12) . ?
S1 N2 1.6069(14) . ?
S1 C9 1.7658(18) . ?
O3 C5 1.367(2) . ?
O3 C8 1.424(3) . ?
N1 C1 1.322(2) . ?
N1 H1A 0.879(10) . ?
N1 H1B 0.875(10) . ?
N2 C1 1.326(2) . ?
C1 C2 1.485(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.399(2) . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.393(2) . ?
C9 C10 1.394(2) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 116.33(8) . . ?
O2 S1 N2 105.92(7) . . ?
O1 S1 N2 114.49(7) . . ?
O2 S1 C9 106.82(8) . . ?
O1 S1 C9 107.36(8) . . ?
N2 S1 C9 105.13(7) . . ?
C5 O3 C8 117.61(17) . . ?
C1 N1 H1A 117.9(15) . . ?
C1 N1 H1B 120.7(15) . . ?
H1A N1 H1B 119(2) . . ?
C1 N2 S1 121.87(12) . . ?
N1 C1 N2 125.61(16) . . ?
N1 C1 C2 118.49(15) . . ?
N2 C1 C2 115.90(15) . . ?
C3 C2 C7 118.52(16) . . ?
C3 C2 C1 122.11(16) . . ?
C7 C2 C1 119.36(16) . . ?
C2 C3 C4 121.25(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.30(18) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
O3 C5 C4 124.24(18) . . ?
O3 C5 C6 115.74(18) . . ?
C4 C5 C6 120.01(17) . . ?
C7 C6 C5 120.28(18) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.61(18) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 121.10(16) . . ?
C14 C9 S1 119.98(13) . . ?
C10 C9 S1 118.93(13) . . ?
C11 C10 C9 119.26(16) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 120.08(18) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.49(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.18(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 118.89(16) . . ?
C13 C14 H14 120.6 . . ?
C9 C14 H14 120.6 . . ?

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
O2 S1 N2 C1 -161.02(13) . . . . ?
O1 S1 N2 C1 -31.46(16) . . . . ?
C9 S1 N2 C1 86.10(15) . . . . ?
S1 N2 C1 N1 3.1(2) . . . . ?
S1 N2 C1 C2 -176.09(11) . . . . ?
N1 C1 C2 C3 16.8(2) . . . . ?
N2 C1 C2 C3 -163.93(17) . . . . ?
N1 C1 C2 C7 -164.34(17) . . . . ?
N2 C1 C2 C7 14.9(2) . . . . ?
C7 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C3 C4 -179.88(17) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C8 O3 C5 C4 -6.7(3) . . . . ?
C8 O3 C5 C6 174.19(18) . . . . ?
C3 C4 C5 O3 179.65(18) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
O3 C5 C6 C7 179.83(19) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C3 C2 C7 C6 -1.9(3) . . . . ?
C1 C2 C7 C6 179.24(18) . . . . ?
O2 S1 C9 C14 145.18(13) . . . . ?
O1 S1 C9 C14 19.73(15) . . . . ?
N2 S1 C9 C14 -102.58(14) . . . . ?
O2 S1 C9 C10 -34.47(15) . . . . ?
O1 S1 C9 C10 -159.92(13) . . . . ?
N2 S1 C9 C10 77.78(14) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
S1 C9 C10 C11 179.91(14) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?
S1 C9 C14 C13 -179.75(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.879(10) 2.073(17) 2.7681(19) 135(2) . yes
N1 H1B O2 0.875(10) 1.990(12) 2.8404(19) 163(2) 1_565 yes
C3 H3 O2 0.95 2.42 3.318(2) 159 1_565 yes
C13 H13 O2 0.95 2.60 3.435(2) 147 3_656 yes

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_structure2h-moca252
_database_code_depnum_ccdc_archive 'CCDC 2400599'
loop_
_audit_author_name
_audit_author_address
'Franc Perdih'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-22 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         'C14 H14 N2 O2 S'
_chemical_formula_sum            'C14 H14 N2 O2 S'
_chemical_formula_weight         274.33

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                   8.5461(2)
_cell_length_b                   23.1470(7)
_cell_length_c                   20.3641(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.362(3)
_cell_angle_gamma                90
_cell_volume                     4024.93(19)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    17669
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.5240
_cell_measurement_theta_min      2.8400

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            37373
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_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             9219
_reflns_number_gt                7697
_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_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0417P)²+2.1175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         9219
_refine_ls_number_parameters     535
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.40719(4) 0.12790(2) 0.49169(2) 0.01884(9) Uani 1 1 d . . . . .
O1 O 0.38514(15) 0.18942(5) 0.48382(6) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.37611(13) 0.10391(5) 0.55508(5) 0.0257(3) Uani 1 1 d . . . . .
N1 N 0.32092(17) 0.15908(6) 0.35266(7) 0.0244(3) Uani 1 1 d D . . . .
H1A H 0.356(2) 0.1867(7) 0.3801(9) 0.029 Uiso 1 1 d D U . . .
H1B H 0.303(2) 0.1661(8) 0.3110(7) 0.029 Uiso 1 1 d D U . . .
N2 N 0.30757(14) 0.09025(6) 0.43823(6) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.28309(16) 0.10809(7) 0.37670(7) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.20311(17) 0.06594(7) 0.33182(7) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.2209(2) 0.00709(8) 0.34343(8) 0.0266(4) Uani 1 1 d . . . . .
H3 H 0.284084 -0.005813 0.380016 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1474(2) -0.03277(8) 0.30216(9) 0.0307(4) Uani 1 1 d . . . . .
H4 H 0.161218 -0.072836 0.310724 0.037 Uiso 1 1 calc R U . . .
C5 C 0.0534(2) -0.01533(8) 0.24818(9) 0.0312(4) Uani 1 1 d . . . . .
C6 C 0.0348(2) 0.04327(8) 0.23764(9) 0.0313(4) Uani 1 1 d . . . . .
H6 H -0.029604 0.056101 0.201397 0.038 Uiso 1 1 calc R U . . .
C7 C 0.10777(19) 0.08385(8) 0.27857(8) 0.0267(4) Uani 1 1 d . . . . .
H7 H 0.092695 0.123898 0.270272 0.032 Uiso 1 1 calc R U . . .
C8 C -0.0233(3) -0.05925(10) 0.20283(11) 0.0470(5) Uani 1 1 d . . . . .
H8A H 0.057391 -0.083136 0.183375 0.071 Uiso 1 1 calc R U . . .
H8B H -0.084257 -0.039349 0.167852 0.071 Uiso 1 1 calc R U . . .
H8C H -0.092896 -0.083864 0.227723 0.071 Uiso 1 1 calc R U . . .
C9 C 0.60343(17) 0.11191(7) 0.47512(7) 0.0202(3) Uani 1 1 d . . . . .
C10 C 0.66147(18) 0.05768(7) 0.49277(8) 0.0245(3) Uani 1 1 d . . . . .
H10 H 0.597030 0.030631 0.514029 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8137(2) 0.04359(9) 0.47905(9) 0.0329(4) Uani 1 1 d . . . . .
H11 H 0.854232 0.006524 0.490364 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9070(2) 0.08360(10) 0.44879(9) 0.0380(5) Uani 1 1 d . . . . .
H12 H 1.012093 0.073976 0.439919 0.046 Uiso 1 1 calc R U . . .
C13 C 0.8490(2) 0.13731(9) 0.43136(9) 0.0374(4) Uani 1 1 d . . . . .
H13 H 0.914211 0.164332 0.410433 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6959(2) 0.15205(8) 0.44427(8) 0.0274(4) Uani 1 1 d . . . . .
H14 H 0.655247 0.188915 0.432207 0.033 Uiso 1 1 calc R U . . .
S3 S 0.25128(4) 0.28718(2) 0.65043(2) 0.01849(9) Uani 1 1 d . . . . .
O5 O 0.37281(13) 0.24780(5) 0.63165(5) 0.0252(2) Uani 1 1 d . . . . .
O6 O 0.24567(13) 0.30103(5) 0.71909(5) 0.0246(2) Uani 1 1 d . . . . .
N5 N 0.36283(18) 0.31108(6) 0.51639(7) 0.0259(3) Uani 1 1 d D . . . .
H5A H 0.372(2) 0.2771(7) 0.5339(9) 0.031 Uiso 1 1 d D U . . .
H5B H 0.392(2) 0.3143(9) 0.4763(8) 0.031 Uiso 1 1 d D U . . .
N6 N 0.25270(16) 0.34762(6) 0.61199(6) 0.0220(3) Uani 1 1 d . . . . .
C29 C 0.30287(17) 0.35279(6) 0.55171(7) 0.0184(3) Uani 1 1 d . . . . .
C30 C 0.28862(17) 0.41151(7) 0.52250(7) 0.0198(3) Uani 1 1 d . . . . .
C31 C 0.2191(2) 0.45524(7) 0.55773(8) 0.0284(4) Uani 1 1 d . . . . .
H31 H 0.181982 0.447355 0.600141 0.034 Uiso 1 1 calc R U . . .
C32 C 0.2034(2) 0.51019(8) 0.53160(9) 0.0335(4) Uani 1 1 d . . . . .
H32 H 0.154829 0.539517 0.556280 0.040 Uiso 1 1 calc R U . . .
C33 C 0.2572(2) 0.52325(7) 0.47001(8) 0.0278(4) Uani 1 1 d . . . . .
C34 C 0.3268(2) 0.47954(8) 0.43545(9) 0.0340(4) Uani 1 1 d . . . . .
H34 H 0.364476 0.487556 0.393158 0.041 Uiso 1 1 calc R U . . .
C35 C 0.3430(2) 0.42441(8) 0.46091(9) 0.0307(4) Uani 1 1 d . . . . .
H35 H 0.391587 0.395183 0.436107 0.037 Uiso 1 1 calc R U . . .
C36 C 0.2408(3) 0.58309(8) 0.44144(10) 0.0409(5) Uani 1 1 d . . . . .
H36A H 0.136893 0.598439 0.450204 0.061 Uiso 1 1 calc R U . . .
H36B H 0.253677 0.581437 0.393877 0.061 Uiso 1 1 calc R U . . .
H36C H 0.321336 0.608324 0.461657 0.061 Uiso 1 1 calc R U . . .
C37 C 0.06822(18) 0.25561(7) 0.62831(7) 0.0211(3) Uani 1 1 d . . . . .
C38 C 0.0602(2) 0.19914(8) 0.60680(9) 0.0312(4) Uani 1 1 d . . . . .
H38 H 0.152700 0.177410 0.600626 0.037 Uiso 1 1 calc R U . . .
C39 C -0.0874(3) 0.17473(9) 0.59435(10) 0.0435(5) Uani 1 1 d . . . . .
H39 H -0.095633 0.135702 0.580183 0.052 Uiso 1 1 calc R U . . .
C40 C -0.2212(2) 0.20667(10) 0.60239(9) 0.0431(5) Uani 1 1 d . . . . .
H40 H -0.320915 0.189527 0.593605 0.052 Uiso 1 1 calc R U . . .
C41 C -0.2118(2) 0.26304(10) 0.62297(9) 0.0389(5) Uani 1 1 d . . . . .
H41 H -0.304614 0.284925 0.627832 0.047 Uiso 1 1 calc R U . . .
C42 C -0.0669(2) 0.28802(8) 0.63666(8) 0.0289(4) Uani 1 1 d . . . . .
H42 H -0.059662 0.326851 0.651580 0.035 Uiso 1 1 calc R U . . .
S2 S 0.55838(4) 0.30388(2) 0.32757(2) 0.01879(9) Uani 1 1 d . . . . .
O3 O 0.53084(15) 0.26526(5) 0.27291(6) 0.0301(3) Uani 1 1 d . . . . .
O4 O 0.47467(13) 0.29118(5) 0.38595(6) 0.0281(3) Uani 1 1 d . . . . .
N3 N 0.46581(18) 0.35917(6) 0.19713(7) 0.0251(3) Uani 1 1 d D . . . .
H3A H 0.469(2) 0.3218(6) 0.1986(10) 0.030 Uiso 1 1 d D U . . .
H3B H 0.446(2) 0.3757(8) 0.1590(8) 0.030 Uiso 1 1 d D U . . .
N4 N 0.52924(15) 0.37082(5) 0.31080(6) 0.0208(3) Uani 1 1 d . . . . .
C15 C 0.48968(17) 0.39023(6) 0.25118(7) 0.0176(3) Uani 1 1 d . . . . .
C16 C 0.46510(17) 0.45344(6) 0.24598(7) 0.0175(3) Uani 1 1 d . . . . .
C17 C 0.36250(19) 0.47687(7) 0.19818(8) 0.0238(3) Uani 1 1 d . . . . .
H17 H 0.313249 0.452482 0.166000 0.029 Uiso 1 1 calc R U . . .
C18 C 0.3322(2) 0.53558(7) 0.19746(8) 0.0265(4) Uani 1 1 d . . . . .
H18 H 0.261189 0.551028 0.164898 0.032 Uiso 1 1 calc R U . . .
C19 C 0.40381(18) 0.57240(7) 0.24357(8) 0.0226(3) Uani 1 1 d . . . . .
C20 C 0.51210(19) 0.54908(7) 0.28916(8) 0.0228(3) Uani 1 1 d . . . . .
H20 H 0.566486 0.573878 0.319454 0.027 Uiso 1 1 calc R U . . .
C21 C 0.54163(18) 0.49035(7) 0.29099(7) 0.0205(3) Uani 1 1 d . . . . .
H21 H 0.614293 0.475062 0.323005 0.025 Uiso 1 1 calc R U . . .
C22 C 0.3610(2) 0.63534(7) 0.24509(9) 0.0313(4) Uani 1 1 d . . . . .
H22A H 0.259854 0.639914 0.265480 0.047 Uiso 1 1 calc R U . . .
H22B H 0.353616 0.650455 0.200120 0.047 Uiso 1 1 calc R U . . .
H22C H 0.441611 0.656683 0.270666 0.047 Uiso 1 1 calc R U . . .
C23 C 0.75943(18) 0.29951(7) 0.35064(8) 0.0202(3) Uani 1 1 d . . . . .
C24 C 0.8655(2) 0.28455(8) 0.30400(9) 0.0313(4) Uani 1 1 d . . . . .
H24 H 0.831332 0.278270 0.259592 0.038 Uiso 1 1 calc R U . . .
C25 C 1.0223(2) 0.27887(9) 0.32304(11) 0.0426(5) Uani 1 1 d . . . . .
H25 H 1.096201 0.268521 0.291486 0.051 Uiso 1 1 calc R U . . .
C26 C 1.0715(2) 0.28808(10) 0.38712(12) 0.0485(6) Uani 1 1 d . . . . .
H26 H 1.179229 0.284227 0.399736 0.058 Uiso 1 1 calc R U . . .
C27 C 0.9652(2) 0.30289(11) 0.43323(11) 0.0518(6) Uani 1 1 d . . . . .
H27 H 0.999841 0.309154 0.477580 0.062 Uiso 1 1 calc R U . . .
C28 C 0.8079(2) 0.30870(9) 0.41527(9) 0.0353(4) Uani 1 1 d . . . . .
H28 H 0.734371 0.318887 0.447036 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4398(11) . ?
S1 O1 1.4444(12) . ?
S1 N2 1.6103(13) . ?
S1 C9 1.7636(16) . ?
N1 C1 1.323(2) . ?
N1 H1A 0.894(15) . ?
N1 H1B 0.872(14) . ?
N2 C1 1.3278(19) . ?
C1 C2 1.484(2) . ?
C2 C3 1.390(2) . ?
C2 C7 1.392(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 C8 1.505(2) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.387(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.381(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
S3 O6 1.4373(11) . ?
S3 O5 1.4452(12) . ?
S3 N6 1.6033(13) . ?
S3 C37 1.7682(16) . ?
N5 C29 1.320(2) . ?
N5 H5A 0.867(15) . ?
N5 H5B 0.867(15) . ?
N6 C29 1.322(2) . ?
C29 C30 1.487(2) . ?
C30 C35 1.388(2) . ?
C30 C31 1.388(2) . ?
C31 C32 1.383(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.387(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.381(3) . ?
C33 C36 1.507(2) . ?
C34 C35 1.382(2) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.379(2) . ?
C37 C42 1.393(2) . ?
C38 C39 1.396(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.377(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.372(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.385(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
S2 O3 1.4395(12) . ?
S2 O4 1.4428(12) . ?
S2 N4 1.6037(13) . ?
S2 C23 1.7653(15) . ?
N3 C15 1.3233(19) . ?
N3 H3A 0.867(15) . ?
N3 H3B 0.876(14) . ?
N4 C15 1.3254(19) . ?
C15 C16 1.481(2) . ?
C16 C17 1.393(2) . ?
C16 C21 1.396(2) . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(2) . ?
C19 C22 1.503(2) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.380(2) . ?
C23 C24 1.384(2) . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.371(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.377(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.385(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 116.85(7) . . ?
O2 S1 N2 106.58(7) . . ?
O1 S1 N2 113.30(7) . . ?
O2 S1 C9 107.61(7) . . ?
O1 S1 C9 107.84(8) . . ?
N2 S1 C9 103.74(7) . . ?
C1 N1 H1A 119.2(13) . . ?
C1 N1 H1B 119.4(13) . . ?
H1A N1 H1B 121.2(18) . . ?
C1 N2 S1 121.87(11) . . ?
N1 C1 N2 126.54(14) . . ?
N1 C1 C2 118.16(13) . . ?
N2 C1 C2 115.29(14) . . ?
C3 C2 C7 118.74(15) . . ?
C3 C2 C1 119.68(14) . . ?
C7 C2 C1 121.57(15) . . ?
C4 C3 C2 120.48(15) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.26(17) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 117.75(16) . . ?
C6 C5 C8 121.57(17) . . ?
C4 C5 C8 120.68(18) . . ?
C5 C6 C7 121.73(16) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C2 120.03(16) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 121.16(15) . . ?
C14 C9 S1 120.69(13) . . ?
C10 C9 S1 118.14(12) . . ?
C11 C10 C9 119.32(16) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.80(17) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.71(17) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.27(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 118.73(17) . . ?
C9 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
O6 S3 O5 116.82(7) . . ?
O6 S3 N6 106.35(7) . . ?
O5 S3 N6 113.65(7) . . ?
O6 S3 C37 105.99(7) . . ?
O5 S3 C37 108.05(7) . . ?
N6 S3 C37 105.11(7) . . ?
C29 N5 H5A 118.2(13) . . ?
C29 N5 H5B 125.7(13) . . ?
H5A N5 H5B 116.1(19) . . ?
C29 N6 S3 122.78(11) . . ?
N5 C29 N6 125.99(14) . . ?
N5 C29 C30 118.55(14) . . ?
N6 C29 C30 115.46(13) . . ?
C35 C30 C31 118.46(15) . . ?
C35 C30 C29 122.23(14) . . ?
C31 C30 C29 119.31(14) . . ?
C32 C31 C30 120.57(16) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C33 121.17(17) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 117.85(16) . . ?
C34 C33 C36 120.78(17) . . ?
C32 C33 C36 121.37(17) . . ?
C33 C34 C35 121.58(17) . . ?
C33 C34 H34 119.2 . . ?
C35 C34 H34 119.2 . . ?
C34 C35 C30 120.37(16) . . ?
C34 C35 H35 119.8 . . ?
C30 C35 H35 119.8 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C42 121.21(16) . . ?
C38 C37 S3 120.31(13) . . ?
C42 C37 S3 118.38(13) . . ?
C37 C38 C39 118.32(18) . . ?
C37 C38 H38 120.8 . . ?
C39 C38 H38 120.8 . . ?
C40 C39 C38 120.64(19) . . ?
C40 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C41 C40 C39 120.54(18) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C42 119.98(19) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
C41 C42 C37 119.30(17) . . ?
C41 C42 H42 120.4 . . ?
C37 C42 H42 120.4 . . ?
O3 S2 O4 116.09(8) . . ?
O3 S2 N4 114.60(7) . . ?
O4 S2 N4 107.13(7) . . ?
O3 S2 C23 107.24(7) . . ?
O4 S2 C23 106.22(7) . . ?
N4 S2 C23 104.65(7) . . ?
C15 N3 H3A 120.6(13) . . ?
C15 N3 H3B 121.2(13) . . ?
H3A N3 H3B 118.1(18) . . ?
C15 N4 S2 123.65(11) . . ?
N3 C15 N4 127.05(14) . . ?
N3 C15 C16 117.43(13) . . ?
N4 C15 C16 115.49(13) . . ?
C17 C16 C21 119.02(14) . . ?
C17 C16 C15 121.18(13) . . ?
C21 C16 C15 119.76(13) . . ?
C18 C17 C16 120.14(14) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 121.17(15) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 118.32(14) . . ?
C18 C19 C22 120.47(15) . . ?
C20 C19 C22 121.18(15) . . ?
C21 C20 C19 120.97(14) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 120.26(14) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 120.91(15) . . ?
C28 C23 S2 119.71(13) . . ?
C24 C23 S2 119.32(12) . . ?
C23 C24 C25 119.02(17) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 120.42(18) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.20(18) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 120.31(19) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C23 C28 C27 119.14(18) . . ?
C23 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?

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
O2 S1 N2 C1 165.39(12) . . . . ?
O1 S1 N2 C1 35.49(15) . . . . ?
C9 S1 N2 C1 -81.17(13) . . . . ?
S1 N2 C1 N1 -6.8(2) . . . . ?
S1 N2 C1 C2 174.05(10) . . . . ?
N1 C1 C2 C3 152.10(15) . . . . ?
N2 C1 C2 C3 -28.7(2) . . . . ?
N1 C1 C2 C7 -29.0(2) . . . . ?
N2 C1 C2 C7 150.18(15) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 -179.97(15) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C8 178.72(17) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C8 C5 C6 C7 -178.70(17) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C3 C2 C7 C6 -1.1(2) . . . . ?
C1 C2 C7 C6 -179.99(15) . . . . ?
O2 S1 C9 C14 -141.30(13) . . . . ?
O1 S1 C9 C14 -14.43(15) . . . . ?
N2 S1 C9 C14 106.00(13) . . . . ?
O2 S1 C9 C10 39.86(14) . . . . ?
O1 S1 C9 C10 166.73(12) . . . . ?
N2 S1 C9 C10 -72.83(13) . . . . ?
C14 C9 C10 C11 -0.2(2) . . . . ?
S1 C9 C10 C11 178.60(13) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C10 C9 C14 C13 -0.3(2) . . . . ?
S1 C9 C14 C13 -179.09(13) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
O6 S3 N6 C29 159.50(12) . . . . ?
O5 S3 N6 C29 29.57(15) . . . . ?
C37 S3 N6 C29 -88.38(14) . . . . ?
S3 N6 C29 N5 -2.8(2) . . . . ?
S3 N6 C29 C30 177.18(10) . . . . ?
N5 C29 C30 C35 -3.2(2) . . . . ?
N6 C29 C30 C35 176.87(15) . . . . ?
N5 C29 C30 C31 176.99(15) . . . . ?
N6 C29 C30 C31 -3.0(2) . . . . ?
C35 C30 C31 C32 0.6(3) . . . . ?
C29 C30 C31 C32 -179.59(16) . . . . ?
C30 C31 C32 C33 -0.4(3) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C31 C32 C33 C36 -179.79(18) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C36 C33 C34 C35 179.92(18) . . . . ?
C33 C34 C35 C30 0.2(3) . . . . ?
C31 C30 C35 C34 -0.4(3) . . . . ?
C29 C30 C35 C34 179.73(16) . . . . ?
O6 S3 C37 C38 -117.10(14) . . . . ?
O5 S3 C37 C38 8.85(15) . . . . ?
N6 S3 C37 C38 130.53(14) . . . . ?
O6 S3 C37 C42 59.38(14) . . . . ?
O5 S3 C37 C42 -174.67(12) . . . . ?
N6 S3 C37 C42 -52.99(14) . . . . ?
C42 C37 C38 C39 -0.9(3) . . . . ?
S3 C37 C38 C39 175.52(14) . . . . ?
C37 C38 C39 C40 1.0(3) . . . . ?
C38 C39 C40 C41 -0.2(3) . . . . ?
C39 C40 C41 C42 -0.8(3) . . . . ?
C40 C41 C42 C37 1.0(3) . . . . ?
C38 C37 C42 C41 -0.1(3) . . . . ?
S3 C37 C42 C41 -176.57(14) . . . . ?
O3 S2 N4 C15 -2.85(16) . . . . ?
O4 S2 N4 C15 -133.18(13) . . . . ?
C23 S2 N4 C15 114.33(14) . . . . ?
S2 N4 C15 N3 1.0(2) . . . . ?
S2 N4 C15 C16 178.89(11) . . . . ?
N3 C15 C16 C17 26.5(2) . . . . ?
N4 C15 C16 C17 -151.54(15) . . . . ?
N3 C15 C16 C21 -155.65(15) . . . . ?
N4 C15 C16 C21 26.3(2) . . . . ?
C21 C16 C17 C18 -2.9(2) . . . . ?
C15 C16 C17 C18 174.97(15) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 2.5(3) . . . . ?
C17 C18 C19 C22 -175.63(16) . . . . ?
C18 C19 C20 C21 -3.5(2) . . . . ?
C22 C19 C20 C21 174.65(15) . . . . ?
C19 C20 C21 C16 1.3(2) . . . . ?
C17 C16 C21 C20 1.9(2) . . . . ?
C15 C16 C21 C20 -175.95(14) . . . . ?
O3 S2 C23 C28 -150.15(15) . . . . ?
O4 S2 C23 C28 -25.41(16) . . . . ?
N4 S2 C23 C28 87.73(15) . . . . ?
O3 S2 C23 C24 27.22(15) . . . . ?
O4 S2 C23 C24 151.96(14) . . . . ?
N4 S2 C23 C24 -94.90(14) . . . . ?
C28 C23 C24 C25 0.0(3) . . . . ?
S2 C23 C24 C25 -177.36(15) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C25 C26 C27 C28 -0.1(4) . . . . ?
C24 C23 C28 C27 0.1(3) . . . . ?
S2 C23 C28 C27 177.45(17) . . . . ?
C26 C27 C28 C23 -0.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.894(15) 2.117(17) 2.7943(18) 131.9(16) . yes
N1 H1B O6 0.872(14) 2.060(15) 2.9188(17) 168.1(18) 4_565 yes
N5 H5A O1 0.867(15) 2.275(18) 2.9011(18) 129.2(17) . yes
N5 H5A O5 0.867(15) 2.103(18) 2.7649(18) 132.7(17) . yes
N5 H5B O4 0.867(15) 2.068(16) 2.8966(19) 159.7(18) . yes
N3 H3A O5 0.867(15) 2.245(17) 2.9076(17) 133.1(16) 4_565 yes
N3 H3A O3 0.867(15) 2.052(18) 2.7102(18) 132.1(17) . yes

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.052

