# 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_glo10593_4aj-major_regioisomer
_database_code_depnum_ccdc_archive 'CCDC 2369683'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-01-26 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         314.39

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.00840(10)
_cell_length_b                   9.2515(2)
_cell_length_c                   15.0308(3)
_cell_angle_alpha                102.5420(10)
_cell_angle_beta                 99.9030(10)
_cell_angle_gamma                102.1910(10)
_cell_volume                     776.13(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7285
_cell_measurement_theta_min      5.1989
_cell_measurement_theta_max      66.6776
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.051
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332

_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11242
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_full        66.67
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             2710
_reflns_number_gt                2468
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0875
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_number_reflns         2710
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.4619P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.45845(7) 0.88648(4) 0.35811(3) 0.01803(13) Uani d . . . 1 . .
N N1 0.6588(2) 0.65525(15) 0.16869(10) 0.0174(3) Uani d . . . 1 . .
N N2 0.2979(2) 0.65118(16) 0.02161(9) 0.0194(3) Uani d . . . 1 . .
O O1 0.47011(19) 0.69424(13) 0.53400(8) 0.0200(3) Uani d . . . 1 . .
O O2 0.10958(19) 0.70655(13) 0.47073(8) 0.0188(3) Uani d . . . 1 . .
C C1 0.3696(3) 0.69251(17) 0.37103(11) 0.0147(3) Uani d . . . 1 . .
C C2 0.1796(3) 0.57984(17) 0.28791(10) 0.0142(3) Uani d . . . 1 . .
H H2A 0.089135 0.630839 0.248924 0.017000 Uiso calc U . R 1 . .
H H2B 0.074242 0.499104 0.306010 0.017000 Uiso calc U . R 1 . .
C C3 0.3769(3) 0.52515(17) 0.24551(10) 0.0132(3) Uani d . . . 1 . .
C C4 0.5496(3) 0.60441(18) 0.34219(10) 0.0147(3) Uani d . . . 1 . .
H H4A 0.580073 0.532745 0.380237 0.018000 Uiso calc U . R 1 . .
H H4B 0.697766 0.671420 0.338333 0.018000 Uiso calc U . R 1 . .
C C5 0.3287(3) 0.69815(17) 0.46794(11) 0.0149(3) Uani d . . . 1 . .
C C6 0.0515(3) 0.7139(2) 0.56086(11) 0.0220(4) Uani d . . . 1 . .
H H6A 0.080081 0.625276 0.582246 0.033000 Uiso calc U . R 1 . .
H H6B -0.113736 0.713025 0.555126 0.033000 Uiso calc U . R 1 . .
H H6C 0.148968 0.808482 0.606238 0.033000 Uiso calc U . R 1 . .
C C7 0.1960(3) 0.9523(2) 0.35926(13) 0.0232(4) Uani d . . . 1 . .
H H7A 0.064190 0.876869 0.313309 0.035000 Uiso calc U . R 1 . .
H H7B 0.218121 1.050808 0.343314 0.035000 Uiso calc U . R 1 . .
H H7C 0.163442 0.964894 0.421786 0.035000 Uiso calc U . R 1 . .
C C8 0.4348(3) 0.59718(16) 0.16753(11) 0.0129(3) Uani d . . . 1 . .
C C9 0.2572(3) 0.59406(17) 0.09304(11) 0.0160(3) Uani d . . . 1 . .
H H9 0.099957 0.549051 0.093401 0.019000 Uiso calc U . R 1 . .
C C10 0.5229(3) 0.71263(18) 0.02486(11) 0.0188(3) Uani d . . . 1 . .
H H10 0.561820 0.757224 -0.023556 0.023000 Uiso calc U . R 1 . .
C C11 0.6995(3) 0.71264(18) 0.09688(12) 0.0194(4) Uani d . . . 1 . .
H H11 0.856775 0.755240 0.095464 0.023000 Uiso calc U . R 1 . .
C C21 0.3368(3) 0.35318(17) 0.20967(10) 0.0141(3) Uani d . . . 1 . .
C C22 0.1177(3) 0.26110(19) 0.15815(11) 0.0182(3) Uani d . . . 1 . .
H H22 -0.010012 0.305671 0.148106 0.022000 Uiso calc U . R 1 . .
C C23 0.0849(3) 0.10506(19) 0.12149(12) 0.0228(4) Uani d . . . 1 . .
H H23 -0.064854 0.043547 0.086289 0.027000 Uiso calc U . R 1 . .
C C24 0.2700(3) 0.03817(19) 0.13597(12) 0.0233(4) Uani d . . . 1 . .
H H24 0.246978 -0.068797 0.110966 0.028000 Uiso calc U . R 1 . .
C C25 0.4882(3) 0.12847(19) 0.18710(12) 0.0211(4) Uani d . . . 1 . .
H H25 0.615317 0.083398 0.197317 0.025000 Uiso calc U . R 1 . .
C C26 0.5212(3) 0.28474(18) 0.22340(11) 0.0171(3) Uani d . . . 1 . .
H H26 0.671563 0.345971 0.258099 0.021000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . 1.8077(17) ?
S1 C1 . 1.8235(15) ?
N1 C8 . 1.335(2) ?
N1 C11 . 1.338(2) ?
N2 C9 . 1.332(2) ?
N2 C10 . 1.339(2) ?
O1 C5 . 1.2031(19) ?
O2 C5 . 1.3424(19) ?
O2 C6 . 1.4469(19) ?
C1 C5 . 1.510(2) ?
C1 C2 . 1.547(2) ?
C1 C4 . 1.550(2) ?
C2 C3 . 1.562(2) ?
C2 H2A . 0.990000 ?
C2 H2B . 0.990000 ?
C3 C21 . 1.517(2) ?
C3 C8 . 1.523(2) ?
C3 C4 . 1.557(2) ?
C4 H4A . 0.990000 ?
C4 H4B . 0.990000 ?
C6 H6A . 0.980000 ?
C6 H6B . 0.980000 ?
C6 H6C . 0.980000 ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C8 C9 . 1.398(2) ?
C9 H9 . 0.950000 ?
C10 C11 . 1.379(2) ?
C10 H10 . 0.950000 ?
C11 H11 . 0.950000 ?
C21 C26 . 1.395(2) ?
C21 C22 . 1.396(2) ?
C22 C23 . 1.387(2) ?
C22 H22 . 0.950000 ?
C23 C24 . 1.390(3) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.386(3) ?
C24 H24 . 0.950000 ?
C25 C26 . 1.388(2) ?
C25 H25 . 0.950000 ?
C26 H26 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 S1 C1 . . 103.00(8) ?
C8 N1 C11 . . 116.22(14) ?
C9 N2 C10 . . 115.68(14) ?
C5 O2 C6 . . 115.36(12) ?
C5 C1 C2 . . 116.92(12) ?
C5 C1 C4 . . 115.85(13) ?
C2 C1 C4 . . 89.39(11) ?
C5 C1 S1 . . 109.97(10) ?
C2 C1 S1 . . 114.46(11) ?
C4 C1 S1 . . 108.76(10) ?
C1 C2 C3 . . 88.97(11) ?
C1 C2 H2A . . 113.800000 ?
C3 C2 H2A . . 113.800000 ?
C1 C2 H2B . . 113.800000 ?
C3 C2 H2B . . 113.800000 ?
H2A C2 H2B . . 111.000000 ?
C21 C3 C8 . . 107.76(12) ?
C21 C3 C4 . . 116.92(12) ?
C8 C3 C4 . . 113.74(12) ?
C21 C3 C2 . . 116.02(12) ?
C8 C3 C2 . . 113.10(12) ?
C4 C3 C2 . . 88.57(11) ?
C1 C4 C3 . . 89.06(11) ?
C1 C4 H4A . . 113.800000 ?
C3 C4 H4A . . 113.800000 ?
C1 C4 H4B . . 113.800000 ?
C3 C4 H4B . . 113.800000 ?
H4A C4 H4B . . 111.000000 ?
O1 C5 O2 . . 123.93(14) ?
O1 C5 C1 . . 125.45(14) ?
O2 C5 C1 . . 110.62(13) ?
O2 C6 H6A . . 109.500000 ?
O2 C6 H6B . . 109.500000 ?
H6A C6 H6B . . 109.500000 ?
O2 C6 H6C . . 109.500000 ?
H6A C6 H6C . . 109.500000 ?
H6B C6 H6C . . 109.500000 ?
S1 C7 H7A . . 109.500000 ?
S1 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
S1 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
N1 C8 C9 . . 120.55(14) ?
N1 C8 C3 . . 118.86(13) ?
C9 C8 C3 . . 120.48(13) ?
N2 C9 C8 . . 123.14(14) ?
N2 C9 H9 . . 118.400000 ?
C8 C9 H9 . . 118.400000 ?
N2 C10 C11 . . 121.50(15) ?
N2 C10 H10 . . 119.200000 ?
C11 C10 H10 . . 119.200000 ?
N1 C11 C10 . . 122.86(14) ?
N1 C11 H11 . . 118.600000 ?
C10 C11 H11 . . 118.600000 ?
C26 C21 C22 . . 118.53(14) ?
C26 C21 C3 . . 120.63(14) ?
C22 C21 C3 . . 120.76(14) ?
C23 C22 C21 . . 120.54(15) ?
C23 C22 H22 . . 119.700000 ?
C21 C22 H22 . . 119.700000 ?
C22 C23 C24 . . 120.35(16) ?
C22 C23 H23 . . 119.800000 ?
C24 C23 H23 . . 119.800000 ?
C25 C24 C23 . . 119.60(15) ?
C25 C24 H24 . . 120.200000 ?
C23 C24 H24 . . 120.200000 ?
C24 C25 C26 . . 120.02(16) ?
C24 C25 H25 . . 120.000000 ?
C26 C25 H25 . . 120.000000 ?
C25 C26 C21 . . 120.95(15) ?
C25 C26 H26 . . 119.500000 ?
C21 C26 H26 . . 119.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 S1 C1 C5 . . . . -68.74(12) ?
C7 S1 C1 C2 . . . . 65.25(12) ?
C7 S1 C1 C4 . . . . 163.42(11) ?
C5 C1 C2 C3 . . . . -134.02(13) ?
C4 C1 C2 C3 . . . . -15.09(11) ?
S1 C1 C2 C3 . . . . 95.31(11) ?
C1 C2 C3 C21 . . . . 134.48(13) ?
C1 C2 C3 C8 . . . . -100.26(13) ?
C1 C2 C3 C4 . . . . 15.02(11) ?
C5 C1 C4 C3 . . . . 135.01(13) ?
C2 C1 C4 C3 . . . . 15.14(11) ?
S1 C1 C4 C3 . . . . -100.56(11) ?
C21 C3 C4 C1 . . . . -133.64(13) ?
C8 C3 C4 C1 . . . . 99.70(13) ?
C2 C3 C4 C1 . . . . -14.99(11) ?
C6 O2 C5 O1 . . . . 1.2(2) ?
C6 O2 C5 C1 . . . . -179.48(12) ?
C2 C1 C5 O1 . . . . 132.52(16) ?
C4 C1 C5 O1 . . . . 29.1(2) ?
S1 C1 C5 O1 . . . . -94.75(17) ?
C2 C1 C5 O2 . . . . -46.79(18) ?
C4 C1 C5 O2 . . . . -150.26(13) ?
S1 C1 C5 O2 . . . . 85.94(13) ?
C11 N1 C8 C9 . . . . 1.8(2) ?
C11 N1 C8 C3 . . . . 177.96(13) ?
C21 C3 C8 N1 . . . . -97.35(15) ?
C4 C3 C8 N1 . . . . 33.96(18) ?
C2 C3 C8 N1 . . . . 133.05(14) ?
C21 C3 C8 C9 . . . . 78.78(17) ?
C4 C3 C8 C9 . . . . -149.90(14) ?
C2 C3 C8 C9 . . . . -50.82(18) ?
C10 N2 C9 C8 . . . . 0.2(2) ?
N1 C8 C9 N2 . . . . -1.9(2) ?
C3 C8 C9 N2 . . . . -178.01(14) ?
C9 N2 C10 C11 . . . . 1.5(2) ?
C8 N1 C11 C10 . . . . -0.2(2) ?
N2 C10 C11 N1 . . . . -1.5(3) ?
C8 C3 C21 C26 . . . . 91.23(16) ?
C4 C3 C21 C26 . . . . -38.3(2) ?
C2 C3 C21 C26 . . . . -140.84(14) ?
C8 C3 C21 C22 . . . . -85.47(17) ?
C4 C3 C21 C22 . . . . 144.99(14) ?
C2 C3 C21 C22 . . . . 42.5(2) ?
C26 C21 C22 C23 . . . . 0.0(2) ?
C3 C21 C22 C23 . . . . 176.72(15) ?
C21 C22 C23 C24 . . . . 0.3(3) ?
C22 C23 C24 C25 . . . . -0.2(3) ?
C23 C24 C25 C26 . . . . -0.1(3) ?
C24 C25 C26 C21 . . . . 0.3(2) ?
C22 C21 C26 C25 . . . . -0.3(2) ?
C3 C21 C26 C25 . . . . -177.03(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6B O1 1_455 0.98 2.43 3.408(2) 176.3 ?
C7 H7C O2 . 0.98 2.62 3.115(2) 111.3 ?

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

data_glo10601_4aj-minor_regioisomer
_database_code_depnum_ccdc_archive 'CCDC 2369684'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-01-26 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         314.39

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.75790(10)
_cell_length_b                   16.2633(4)
_cell_length_c                   16.7223(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.8740(10)
_cell_angle_gamma                90
_cell_volume                     1557.70(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      3.8011
_cell_measurement_theta_max      66.6561
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.057
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            28260
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_full        66.74
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             2755
_reflns_number_gt                2397
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0796
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.019
_refine_ls_number_reflns         2755
_refine_ls_number_parameters     270
_refine_ls_number_restraints     173
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+1.2152P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.06601(7) 0.27520(2) 0.71544(2) 0.02000(13) Uani d . . . 1.000000 . .
C C1 0.1969(3) 0.36312(10) 0.66887(9) 0.0150(3) Uani d . . . 1.000000 . .
C C2 0.0559(3) 0.37347(10) 0.58463(9) 0.0159(3) Uani d . . . 1.000000 . .
H H2A -0.092050 0.342033 0.578439 0.019000 Uiso calc U . R 1.000000 . .
H H2B 0.029392 0.431537 0.568434 0.019000 Uiso calc U . R 1.000000 . .
C C3 0.2564(3) 0.33182(10) 0.54483(9) 0.0147(3) Uani d . . . 1.000000 . .
C C4 0.4152(3) 0.33993(10) 0.62620(9) 0.0164(3) Uani d . . . 1.000000 . .
H H4A 0.489310 0.287611 0.645320 0.020000 Uiso calc U . R 1.000000 . .
H H4B 0.532280 0.384541 0.626462 0.020000 Uiso calc U . R 1.000000 . .
C C5 0.3480(3) 0.38275(10) 0.47822(9) 0.0169(3) Uani d U . D 1.000000 . .
O O1 0.2662(13) 0.4463(4) 0.4502(4) 0.0249(10) Uani d U P D 0.77(3) A 1
O O2 0.5453(10) 0.3501(5) 0.4566(5) 0.0175(10) Uani d U P D 0.77(3) A 1
C C6 0.6659(12) 0.3953(5) 0.3987(4) 0.0227(11) Uani d U P D 0.77(3) A 1
H H6A 0.554932 0.410360 0.352690 0.034000 Uiso calc U P R 0.77(3) A 1
H H6B 0.789728 0.360907 0.380399 0.034000 Uiso calc U P R 0.77(3) A 1
H H6C 0.734608 0.445259 0.423977 0.034000 Uiso calc U P R 0.77(3) A 1
O O1A 0.217(3) 0.4295(15) 0.4407(13) 0.028(4) Uani d U P D 0.23(3) A 2
O O2A 0.562(3) 0.3614(15) 0.4640(16) 0.020(4) Uani d U P D 0.23(3) A 2
C C6A 0.654(5) 0.4114(17) 0.4021(16) 0.0227(11) Uani d U P D 0.23(3) A 2
H H61 0.577887 0.395770 0.349261 0.034000 Uiso calc U P R 0.23(3) A 2
H H62 0.822852 0.402514 0.403452 0.034000 Uiso calc U P R 0.23(3) A 2
H H63 0.623732 0.469631 0.412130 0.034000 Uiso calc U P R 0.23(3) A 2
C C7 0.2797(3) 0.25362(12) 0.79904(10) 0.0282(4) Uani d . . . 1.000000 . .
H H7A 0.430823 0.242373 0.779177 0.042000 Uiso calc U . R 1.000000 . .
H H7B 0.230296 0.205526 0.828298 0.042000 Uiso calc U . R 1.000000 . .
H H7C 0.294223 0.301200 0.835159 0.042000 Uiso calc U . R 1.000000 . .
C C11 0.2148(3) 0.24368(10) 0.51681(9) 0.0157(3) Uani d U . D 1.000000 . .
N N1 0.0099(18) 0.2228(7) 0.4894(9) 0.026(3) Uani d U P D 0.515(11) B 1
C C12 -0.047(3) 0.1438(10) 0.4571(10) 0.034(3) Uani d U P D 0.515(11) B 1
H H12 -0.200935 0.128858 0.436165 0.041000 Uiso calc U P R 0.515(11) B 1
C C13 0.131(2) 0.0931(7) 0.4586(8) 0.020(2) Uani d U P D 0.515(11) B 1
H H13 0.104867 0.038942 0.438431 0.024000 Uiso calc U P R 0.515(11) B 1
N N2 0.363(2) 0.1157(8) 0.4892(9) 0.014(2) Uani d U P D 0.515(11) B 1
C C14 0.415(2) 0.1894(9) 0.5157(11) 0.014(2) Uani d U P D 0.515(11) B 1
H H14 0.570433 0.206163 0.532829 0.017000 Uiso calc U P R 0.515(11) B 1
N N1A 0.3885(19) 0.1948(8) 0.5184(10) 0.017(3) Uani d U P D 0.485(11) B 2
C C12A 0.388(3) 0.1129(12) 0.4908(14) 0.030(5) Uani d U P D 0.485(11) B 2
H H12A 0.523945 0.080347 0.488849 0.037000 Uiso calc U P R 0.485(11) B 2
C C13A 0.173(2) 0.0870(7) 0.4680(8) 0.017(2) Uani d U P D 0.485(11) B 2
H H13A 0.154099 0.031560 0.450708 0.020000 Uiso calc U P R 0.485(11) B 2
N N2A -0.030(2) 0.1367(8) 0.4676(8) 0.022(2) Uani d U P D 0.485(11) B 2
C C14A -0.016(2) 0.2130(9) 0.4901(10) 0.017(2) Uani d U P D 0.485(11) B 2
H H14A -0.151039 0.246924 0.489221 0.021000 Uiso calc U P R 0.485(11) B 2
C C21 0.2198(3) 0.43638(10) 0.72426(9) 0.0151(3) Uani d . . . 1.000000 . .
C C22 0.4281(3) 0.45158(11) 0.77227(9) 0.0186(3) Uani d . . . 1.000000 . .
H H22 0.555974 0.414939 0.770617 0.022000 Uiso calc U . R 1.000000 . .
C C23 0.4501(3) 0.51989(11) 0.82252(10) 0.0234(4) Uani d . . . 1.000000 . .
H H23 0.592748 0.529693 0.854927 0.028000 Uiso calc U . R 1.000000 . .
C C24 0.2649(3) 0.57356(11) 0.82541(10) 0.0246(4) Uani d . . . 1.000000 . .
H H24 0.280424 0.620516 0.859328 0.030000 Uiso calc U . R 1.000000 . .
C C25 0.0561(3) 0.55845(10) 0.77844(10) 0.0225(4) Uani d . . . 1.000000 . .
H H25 -0.071887 0.594963 0.780618 0.027000 Uiso calc U . R 1.000000 . .
C C26 0.0336(3) 0.49032(10) 0.72838(9) 0.0176(3) Uani d . . . 1.000000 . .
H H26 -0.110067 0.480364 0.696629 0.021000 Uiso calc U . R 1.000000 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . 1.7997(18) ?
S1 C1 . 1.8274(16) ?
C1 C21 . 1.507(2) ?
C1 C4 . 1.554(2) ?
C1 C2 . 1.561(2) ?
C2 C3 . 1.547(2) ?
C2 H2A . 0.990000 ?
C2 H2B . 0.990000 ?
C3 C11 . 1.519(2) ?
C3 C5 . 1.525(2) ?
C3 C4 . 1.565(2) ?
C4 H4A . 0.990000 ?
C4 H4B . 0.990000 ?
C5 O1A . 1.200(12) ?
C5 O1 . 1.210(4) ?
C5 O2A . 1.325(14) ?
C5 O2 . 1.337(4) ?
O2 C6 . 1.448(5) ?
C6 H6A . 0.980000 ?
C6 H6B . 0.980000 ?
C6 H6C . 0.980000 ?
O2A C6A . 1.458(16) ?
C6A H61 . 0.980000 ?
C6A H62 . 0.980000 ?
C6A H63 . 0.980000 ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C11 N1 . 1.267(11) ?
C11 N1A . 1.277(11) ?
C11 C14A . 1.449(13) ?
C11 C14 . 1.455(14) ?
N1 C12 . 1.419(19) ?
C12 C13 . 1.317(19) ?
C12 H12 . 0.950000 ?
C13 N2 . 1.427(16) ?
C13 H13 . 0.950000 ?
N2 C14 . 1.301(18) ?
C14 H14 . 0.950000 ?
N1A C12A . 1.41(2) ?
C12A C13A . 1.32(2) ?
C12A H12A . 0.950000 ?
C13A N2A . 1.420(17) ?
C13A H13A . 0.950000 ?
N2A C14A . 1.298(18) ?
C14A H14A . 0.950000 ?
C21 C26 . 1.392(2) ?
C21 C22 . 1.395(2) ?
C22 C23 . 1.391(2) ?
C22 H22 . 0.950000 ?
C23 C24 . 1.383(3) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.389(3) ?
C24 H24 . 0.950000 ?
C25 C26 . 1.387(2) ?
C25 H25 . 0.950000 ?
C26 H26 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 S1 C1 . . 101.81(8) ?
C21 C1 C4 . . 116.76(13) ?
C21 C1 C2 . . 118.30(13) ?
C4 C1 C2 . . 88.98(11) ?
C21 C1 S1 . . 111.76(11) ?
C4 C1 S1 . . 113.20(11) ?
C2 C1 S1 . . 105.66(10) ?
C3 C2 C1 . . 89.95(11) ?
C3 C2 H2A . . 113.700000 ?
C1 C2 H2A . . 113.700000 ?
C3 C2 H2B . . 113.700000 ?
C1 C2 H2B . . 113.700000 ?
H2A C2 H2B . . 110.900000 ?
C11 C3 C5 . . 110.04(13) ?
C11 C3 C2 . . 116.40(13) ?
C5 C3 C2 . . 113.92(13) ?
C11 C3 C4 . . 114.03(13) ?
C5 C3 C4 . . 111.99(13) ?
C2 C3 C4 . . 89.10(11) ?
C1 C4 C3 . . 89.52(11) ?
C1 C4 H4A . . 113.700000 ?
C3 C4 H4A . . 113.700000 ?
C1 C4 H4B . . 113.700000 ?
C3 C4 H4B . . 113.700000 ?
H4A C4 H4B . . 111.000000 ?
O1A C5 O2A . . 128.1(13) ?
O1 C5 O2 . . 122.8(4) ?
O1A C5 C3 . . 118.8(10) ?
O1 C5 C3 . . 126.7(3) ?
O2A C5 C3 . . 112.7(9) ?
O2 C5 C3 . . 110.4(3) ?
C5 O2 C6 . . 117.2(5) ?
O2 C6 H6A . . 109.500000 ?
O2 C6 H6B . . 109.500000 ?
H6A C6 H6B . . 109.500000 ?
O2 C6 H6C . . 109.500000 ?
H6A C6 H6C . . 109.500000 ?
H6B C6 H6C . . 109.500000 ?
C5 O2A C6A . . 113.2(16) ?
O2A C6A H61 . . 109.500000 ?
O2A C6A H62 . . 109.500000 ?
H61 C6A H62 . . 109.500000 ?
O2A C6A H63 . . 109.500000 ?
H61 C6A H63 . . 109.500000 ?
H62 C6A H63 . . 109.500000 ?
S1 C7 H7A . . 109.500000 ?
S1 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
S1 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
N1A C11 C14A . . 119.0(6) ?
N1 C11 C14 . . 122.9(6) ?
N1 C11 C3 . . 118.4(5) ?
N1A C11 C3 . . 118.9(6) ?
C14A C11 C3 . . 122.1(6) ?
C14 C11 C3 . . 118.4(6) ?
C11 N1 C12 . . 123.4(11) ?
C13 C12 N1 . . 114.2(14) ?
C13 C12 H12 . . 122.900000 ?
N1 C12 H12 . . 122.900000 ?
C12 C13 N2 . . 123.0(10) ?
C12 C13 H13 . . 118.500000 ?
N2 C13 H13 . . 118.500000 ?
C14 N2 C13 . . 122.3(12) ?
N2 C14 C11 . . 114.0(12) ?
N2 C14 H14 . . 123.000000 ?
C11 C14 H14 . . 123.000000 ?
C11 N1A C12A . . 127.3(12) ?
C13A C12A N1A . . 111.6(15) ?
C13A C12A H12A . . 124.200000 ?
N1A C12A H12A . . 124.200000 ?
C12A C13A N2A . . 124.3(10) ?
C12A C13A H13A . . 117.900000 ?
N2A C13A H13A . . 117.900000 ?
C14A N2A C13A . . 121.3(12) ?
N2A C14A C11 . . 116.3(11) ?
N2A C14A H14A . . 121.800000 ?
C11 C14A H14A . . 121.800000 ?
C26 C21 C22 . . 118.73(15) ?
C26 C21 C1 . . 120.61(14) ?
C22 C21 C1 . . 120.65(14) ?
C23 C22 C21 . . 120.60(16) ?
C23 C22 H22 . . 119.700000 ?
C21 C22 H22 . . 119.700000 ?
C24 C23 C22 . . 120.15(16) ?
C24 C23 H23 . . 119.900000 ?
C22 C23 H23 . . 119.900000 ?
C23 C24 C25 . . 119.64(16) ?
C23 C24 H24 . . 120.200000 ?
C25 C24 H24 . . 120.200000 ?
C26 C25 C24 . . 120.31(16) ?
C26 C25 H25 . . 119.800000 ?
C24 C25 H25 . . 119.800000 ?
C25 C26 C21 . . 120.56(16) ?
C25 C26 H26 . . 119.700000 ?
C21 C26 H26 . . 119.700000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 S1 C1 C21 . . . . -63.26(13) ?
C7 S1 C1 C4 . . . . 71.05(12) ?
C7 S1 C1 C2 . . . . 166.80(11) ?
C21 C1 C2 C3 . . . . 132.01(14) ?
C4 C1 C2 C3 . . . . 11.88(12) ?
S1 C1 C2 C3 . . . . -101.96(11) ?
C1 C2 C3 C11 . . . . 104.75(14) ?
C1 C2 C3 C5 . . . . -125.55(13) ?
C1 C2 C3 C4 . . . . -11.80(12) ?
C21 C1 C4 C3 . . . . -133.22(14) ?
C2 C1 C4 C3 . . . . -11.74(12) ?
S1 C1 C4 C3 . . . . 94.88(12) ?
C11 C3 C4 C1 . . . . -106.83(14) ?
C5 C3 C4 C1 . . . . 127.39(13) ?
C2 C3 C4 C1 . . . . 11.85(12) ?
C11 C3 C5 O1A . . . . 104.1(16) ?
C2 C3 C5 O1A . . . . -28.7(16) ?
C4 C3 C5 O1A . . . . -128.0(16) ?
C11 C3 C5 O1 . . . . 125.6(5) ?
C2 C3 C5 O1 . . . . -7.2(5) ?
C4 C3 C5 O1 . . . . -106.5(5) ?
C11 C3 C5 O2A . . . . -68.8(14) ?
C2 C3 C5 O2A . . . . 158.4(14) ?
C4 C3 C5 O2A . . . . 59.2(14) ?
C11 C3 C5 O2 . . . . -58.1(5) ?
C2 C3 C5 O2 . . . . 169.1(5) ?
C4 C3 C5 O2 . . . . 69.9(5) ?
O1 C5 O2 C6 . . . . 1.8(9) ?
C3 C5 O2 C6 . . . . -174.7(6) ?
O1A C5 O2A C6A . . . . 10.(3) ?
C3 C5 O2A C6A . . . . -178.2(17) ?
C5 C3 C11 N1 . . . . -96.7(8) ?
C2 C3 C11 N1 . . . . 34.8(8) ?
C4 C3 C11 N1 . . . . 136.5(8) ?
C5 C3 C11 N1A . . . . 80.2(9) ?
C2 C3 C11 N1A . . . . -148.3(9) ?
C4 C3 C11 N1A . . . . -46.6(9) ?
C5 C3 C11 C14A . . . . -101.3(8) ?
C2 C3 C11 C14A . . . . 30.2(8) ?
C4 C3 C11 C14A . . . . 131.9(8) ?
C5 C3 C11 C14 . . . . 77.7(9) ?
C2 C3 C11 C14 . . . . -150.8(9) ?
C4 C3 C11 C14 . . . . -49.1(9) ?
C14 C11 N1 C12 . . . . 2.(2) ?
C3 C11 N1 C12 . . . . 176.1(12) ?
C11 N1 C12 C13 . . . . 1.(2) ?
N1 C12 C13 N2 . . . . -1.(2) ?
C12 C13 N2 C14 . . . . -2.(2) ?
C13 N2 C14 C11 . . . . 4.(2) ?
N1 C11 C14 N2 . . . . -4.(2) ?
C3 C11 C14 N2 . . . . -178.6(11) ?
C14A C11 N1A C12A . . . . 5.(2) ?
C3 C11 N1A C12A . . . . -176.0(16) ?
C11 N1A C12A C13A . . . . -6.(3) ?
N1A C12A C13A N2A . . . . 3.(3) ?
C12A C13A N2A C14A . . . . 0.(3) ?
C13A N2A C14A C11 . . . . -1.(2) ?
N1A C11 C14A N2A . . . . -1.5(19) ?
C3 C11 C14A N2A . . . . 179.9(10) ?
C4 C1 C21 C26 . . . . 142.48(15) ?
C2 C1 C21 C26 . . . . 38.1(2) ?
S1 C1 C21 C26 . . . . -84.96(16) ?
C4 C1 C21 C22 . . . . -37.4(2) ?
C2 C1 C21 C22 . . . . -141.80(15) ?
S1 C1 C21 C22 . . . . 95.17(15) ?
C26 C21 C22 C23 . . . . -0.8(2) ?
C1 C21 C22 C23 . . . . 179.06(15) ?
C21 C22 C23 C24 . . . . 0.1(2) ?
C22 C23 C24 C25 . . . . 0.6(3) ?
C23 C24 C25 C26 . . . . -0.5(2) ?
C24 C25 C26 C21 . . . . -0.2(2) ?
C22 C21 C26 C25 . . . . 0.9(2) ?
C1 C21 C26 C25 . . . . -178.97(14) ?

####################################################################### 
# 
# 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_glo10599_9
_database_code_depnum_ccdc_archive 'CCDC 2369685'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-07-10 deposited with the CCDC.	2025-01-26 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N3 O S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         341.44

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.7580(4)
_cell_length_b                   7.7718(3)
_cell_length_c                   38.4713(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3216.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6252
_cell_measurement_theta_min      2.1690
_cell_measurement_theta_max      27.1204
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.039
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424

_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            35150
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       50

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             3686
_reflns_number_gt                2932
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1041
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_number_reflns         3686
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.6964P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.62632(4) 0.07186(5) 0.36806(2) 0.02077(13) Uani d . . . 1 . .
S S2 0.24582(4) 0.09288(5) 0.30565(2) 0.02055(13) Uani d . . . 1 . .
O O1 0.30030(13) 0.06827(18) 0.38046(3) 0.0324(3) Uani d . . . 1 . .
N N1 0.45659(17) 0.7966(2) 0.47841(4) 0.0330(4) Uani d . . . 1 . .
N N2 0.61645(15) 0.5371(2) 0.45404(4) 0.0271(3) Uani d . . . 1 . .
N N3 0.45704(13) 0.25699(17) 0.30903(4) 0.0184(3) Uani d . . . 1 . .
C C1 0.50035(16) 0.2056(2) 0.38429(4) 0.0188(3) Uani d . . . 1 . .
C C2 0.48411(17) 0.2192(2) 0.42404(5) 0.0215(4) Uani d . . . 1 . .
H H2A 0.561668 0.199901 0.437333 0.026000 Uiso calc U . R 1 . .
H H2B 0.415094 0.148698 0.433364 0.026000 Uiso calc U . R 1 . .
C C3 0.45068(17) 0.4123(2) 0.41892(5) 0.0216(4) Uani d . . . 1 . .
H H3 0.359075 0.425604 0.415412 0.026000 Uiso calc U . R 1 . .
C C4 0.51826(17) 0.4038(2) 0.38309(5) 0.0211(4) Uani d . . . 1 . .
H H4A 0.472786 0.461162 0.363958 0.025000 Uiso calc U . R 1 . .
H H4B 0.606224 0.440990 0.383837 0.025000 Uiso calc U . R 1 . .
C C5 0.38340(16) 0.1456(2) 0.36579(5) 0.0205(4) Uani d . . . 1 . .
C C6 0.37458(15) 0.1763(2) 0.32760(5) 0.0182(3) Uani d . . . 1 . .
C C7 0.5927(2) -0.1234(2) 0.39160(6) 0.0333(5) Uani d . . . 1 . .
H H7A 0.598608 -0.101344 0.416624 0.050000 Uiso calc U . R 1 . .
H H7B 0.652704 -0.212491 0.385042 0.050000 Uiso calc U . R 1 . .
H H7C 0.508466 -0.162304 0.385909 0.050000 Uiso calc U . R 1 . .
C C11 0.49658(17) 0.5423(2) 0.44454(4) 0.0222(4) Uani d . . . 1 . .
C C12 0.41778(19) 0.6710(2) 0.45724(5) 0.0279(4) Uani d . . . 1 . .
H H12 0.332818 0.669166 0.450510 0.033000 Uiso calc U . R 1 . .
C C13 0.5765(2) 0.7909(2) 0.48704(5) 0.0309(4) Uani d . . . 1 . .
H H13 0.609190 0.878330 0.501686 0.037000 Uiso calc U . R 1 . .
C C14 0.6552(2) 0.6621(2) 0.47540(5) 0.0300(4) Uani d . . . 1 . .
H H14 0.739436 0.662464 0.482817 0.036000 Uiso calc U . R 1 . .
C C21 0.30900(15) 0.1701(2) 0.26738(5) 0.0188(3) Uani d . . . 1 . .
C C22 0.42200(15) 0.2551(2) 0.27439(4) 0.0173(3) Uani d . . . 1 . .
C C23 0.49253(16) 0.3245(2) 0.24719(5) 0.0200(4) Uani d . . . 1 . .
H H23 0.568044 0.383701 0.251751 0.024000 Uiso calc U . R 1 . .
C C24 0.44970(17) 0.3049(2) 0.21355(5) 0.0228(4) Uani d . . . 1 . .
H H24 0.496873 0.350178 0.194785 0.027000 Uiso calc U . R 1 . .
C C25 0.33777(17) 0.2193(2) 0.20672(5) 0.0238(4) Uani d . . . 1 . .
H H25 0.310671 0.207218 0.183343 0.029000 Uiso calc U . R 1 . .
C C26 0.26576(16) 0.1518(2) 0.23321(5) 0.0213(4) Uani d . . . 1 . .
H H26 0.189508 0.094933 0.228404 0.026000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . 1.8034(19) ?
S1 C1 . 1.8185(17) ?
S2 C21 . 1.7289(18) ?
S2 C6 . 1.7472(17) ?
O1 C5 . 1.216(2) ?
N1 C13 . 1.333(3) ?
N1 C12 . 1.338(2) ?
N2 C14 . 1.339(2) ?
N2 C11 . 1.341(2) ?
N3 C6 . 1.300(2) ?
N3 C22 . 1.385(2) ?
C1 C5 . 1.519(2) ?
C1 C2 . 1.543(2) ?
C1 C4 . 1.553(2) ?
C2 C3 . 1.556(2) ?
C2 H2A . 0.990000 ?
C2 H2B . 0.990000 ?
C3 C11 . 1.495(2) ?
C3 C4 . 1.560(2) ?
C3 H3 . 1.000000 ?
C4 H4A . 0.990000 ?
C4 H4B . 0.990000 ?
C5 C6 . 1.492(2) ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C11 C12 . 1.399(3) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.386(3) ?
C13 H13 . 0.950000 ?
C14 H14 . 0.950000 ?
C21 C26 . 1.402(2) ?
C21 C22 . 1.410(2) ?
C22 C23 . 1.401(2) ?
C23 C24 . 1.382(3) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.401(3) ?
C24 H24 . 0.950000 ?
C25 C26 . 1.383(3) ?
C25 H25 . 0.950000 ?
C26 H26 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 S1 C1 . . 99.16(9) ?
C21 S2 C6 . . 88.34(8) ?
C13 N1 C12 . . 115.44(17) ?
C14 N2 C11 . . 116.42(17) ?
C6 N3 C22 . . 109.74(14) ?
C5 C1 C2 . . 113.05(14) ?
C5 C1 C4 . . 113.17(14) ?
C2 C1 C4 . . 88.61(13) ?
C5 C1 S1 . . 106.32(11) ?
C2 C1 S1 . . 117.62(12) ?
C4 C1 S1 . . 117.67(12) ?
C1 C2 C3 . . 88.08(13) ?
C1 C2 H2A . . 114.000000 ?
C3 C2 H2A . . 114.000000 ?
C1 C2 H2B . . 114.000000 ?
C3 C2 H2B . . 114.000000 ?
H2A C2 H2B . . 111.200000 ?
C11 C3 C2 . . 119.46(15) ?
C11 C3 C4 . . 117.22(15) ?
C2 C3 C4 . . 87.89(12) ?
C11 C3 H3 . . 110.200000 ?
C2 C3 H3 . . 110.200000 ?
C4 C3 H3 . . 110.200000 ?
C1 C4 C3 . . 87.60(13) ?
C1 C4 H4A . . 114.100000 ?
C3 C4 H4A . . 114.100000 ?
C1 C4 H4B . . 114.100000 ?
C3 C4 H4B . . 114.100000 ?
H4A C4 H4B . . 111.200000 ?
O1 C5 C6 . . 119.30(16) ?
O1 C5 C1 . . 122.91(16) ?
C6 C5 C1 . . 117.72(14) ?
N3 C6 C5 . . 125.10(15) ?
N3 C6 S2 . . 117.03(13) ?
C5 C6 S2 . . 117.85(12) ?
S1 C7 H7A . . 109.500000 ?
S1 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
S1 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
N2 C11 C12 . . 120.60(17) ?
N2 C11 C3 . . 118.48(16) ?
C12 C11 C3 . . 120.86(17) ?
N1 C12 C11 . . 123.02(19) ?
N1 C12 H12 . . 118.500000 ?
C11 C12 H12 . . 118.500000 ?
N1 C13 C14 . . 122.33(18) ?
N1 C13 H13 . . 118.800000 ?
C14 C13 H13 . . 118.800000 ?
N2 C14 C13 . . 122.16(19) ?
N2 C14 H14 . . 118.900000 ?
C13 C14 H14 . . 118.900000 ?
C26 C21 C22 . . 120.88(16) ?
C26 C21 S2 . . 129.27(14) ?
C22 C21 S2 . . 109.80(13) ?
N3 C22 C23 . . 124.56(15) ?
N3 C22 C21 . . 115.08(15) ?
C23 C22 C21 . . 120.31(15) ?
C24 C23 C22 . . 118.46(16) ?
C24 C23 H23 . . 120.800000 ?
C22 C23 H23 . . 120.800000 ?
C23 C24 C25 . . 120.97(17) ?
C23 C24 H24 . . 119.500000 ?
C25 C24 H24 . . 119.500000 ?
C26 C25 C24 . . 121.55(17) ?
C26 C25 H25 . . 119.200000 ?
C24 C25 H25 . . 119.200000 ?
C25 C26 C21 . . 117.82(16) ?
C25 C26 H26 . . 121.100000 ?
C21 C26 H26 . . 121.100000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 S1 C1 C5 . . . . -75.70(13) ?
C7 S1 C1 C2 . . . . 52.16(15) ?
C7 S1 C1 C4 . . . . 156.24(14) ?
C5 C1 C2 C3 . . . . -93.64(15) ?
C4 C1 C2 C3 . . . . 21.02(13) ?
S1 C1 C2 C3 . . . . 141.79(12) ?
C1 C2 C3 C11 . . . . -141.25(16) ?
C1 C2 C3 C4 . . . . -20.93(13) ?
C5 C1 C4 C3 . . . . 93.58(15) ?
C2 C1 C4 C3 . . . . -20.98(13) ?
S1 C1 C4 C3 . . . . -141.70(12) ?
C11 C3 C4 C1 . . . . 143.11(15) ?
C2 C3 C4 C1 . . . . 20.80(13) ?
C2 C1 C5 O1 . . . . -20.8(2) ?
C4 C1 C5 O1 . . . . -119.63(19) ?
S1 C1 C5 O1 . . . . 109.70(17) ?
C2 C1 C5 C6 . . . . 162.34(14) ?
C4 C1 C5 C6 . . . . 63.52(19) ?
S1 C1 C5 C6 . . . . -67.15(16) ?
C22 N3 C6 C5 . . . . 177.26(15) ?
C22 N3 C6 S2 . . . . -0.91(18) ?
O1 C5 C6 N3 . . . . -179.98(16) ?
C1 C5 C6 N3 . . . . -3.0(2) ?
O1 C5 C6 S2 . . . . -1.8(2) ?
C1 C5 C6 S2 . . . . 175.15(12) ?
C21 S2 C6 N3 . . . . 1.03(13) ?
C21 S2 C6 C5 . . . . -177.28(13) ?
C14 N2 C11 C12 . . . . -1.2(3) ?
C14 N2 C11 C3 . . . . 176.11(16) ?
C2 C3 C11 N2 . . . . 47.2(2) ?
C4 C3 C11 N2 . . . . -56.9(2) ?
C2 C3 C11 C12 . . . . -135.52(18) ?
C4 C3 C11 C12 . . . . 120.43(19) ?
C13 N1 C12 C11 . . . . -0.5(3) ?
N2 C11 C12 N1 . . . . 1.7(3) ?
C3 C11 C12 N1 . . . . -175.54(17) ?
C12 N1 C13 C14 . . . . -1.1(3) ?
C11 N2 C14 C13 . . . . -0.4(3) ?
N1 C13 C14 N2 . . . . 1.6(3) ?
C6 S2 C21 C26 . . . . 176.42(17) ?
C6 S2 C21 C22 . . . . -0.78(12) ?
C6 N3 C22 C23 . . . . -177.30(15) ?
C6 N3 C22 C21 . . . . 0.2(2) ?
C26 C21 C22 N3 . . . . -176.99(15) ?
S2 C21 C22 N3 . . . . 0.49(18) ?
C26 C21 C22 C23 . . . . 0.7(2) ?
S2 C21 C22 C23 . . . . 178.15(12) ?
N3 C22 C23 C24 . . . . 176.33(15) ?
C21 C22 C23 C24 . . . . -1.1(2) ?
C22 C23 C24 C25 . . . . 0.7(2) ?
C23 C24 C25 C26 . . . . 0.2(3) ?
C24 C25 C26 C21 . . . . -0.7(2) ?
C22 C21 C26 C25 . . . . 0.2(2) ?
S2 C21 C26 C25 . . . . -176.72(13) ?

