# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_12570-lia603
_database_code_depnum_ccdc_archive 'CCDC 2167839'
loop_
_audit_author_name
_audit_author_address
"Dar'ya Spiridonova"
;St Petersburg University
Russia
;
_audit_update_record             
;
2022-04-21 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N4 O2 S'
_chemical_formula_sum            'C17 H14 N4 O2 S'
_chemical_formula_weight         338.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H14 N4 O2 S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6565(4)
_cell_length_b                   44.4687(14)
_cell_length_c                   9.8470(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.866(5)
_cell_angle_gamma                90
_cell_volume                     3132.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.9440
_cell_measurement_theta_min      2.8630
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       62
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34619
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         2.605
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2096
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00   5.50   0.75   22.66    --  -25.43  57.00   0.00   66
  2  ω    -94.00 -67.00   0.75   22.66    --  -25.43 -57.00  30.00   36
  3  ω     11.50  43.00   0.75   22.66    --  -25.43  57.00   0.00   42
  4  ω      1.75  43.00   0.75   22.66    --  -25.43  57.00-180.00   55
  5  ω    -42.00  56.25   0.75   22.66    --   26.52 -77.00 120.00  131
  6  ω     -2.00  91.00   0.75   22.66    --   26.52  77.00-120.00  124
  7  ω     36.00 101.25   0.75   22.66    --   26.52 178.00 -60.00   87
  8  ω    -12.00  67.50   0.75   22.66    --   26.52 -99.00  60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0004799000
_diffrn_orient_matrix_UB_12      0.0155864000
_diffrn_orient_matrix_UB_13      0.0154817000
_diffrn_orient_matrix_UB_21      0.0774353000
_diffrn_orient_matrix_UB_22      -0.0020985000
_diffrn_orient_matrix_UB_23      0.0653821000
_diffrn_orient_matrix_UB_31      0.0616153000
_diffrn_orient_matrix_UB_32      0.0027566000
_diffrn_orient_matrix_UB_33      -0.0379668000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8458
_reflns_number_total             9126
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         9126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.1175
_refine_ls_restrained_S_all      1.299
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+21.1826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2181
_refine_ls_wR_factor_ref         0.2212
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C3'(H3')
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C1'(H1'), C6'(H6'), C7'(H7'), C8'(H8'), C9'(H9'),
 C10'(H10'), C12'(H12'), C13'(H13'), C15'(H15'), C16'(H16')
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17'(H17D,H17E,H17F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.30848(14) 0.31527(2) -0.25721(11) 0.01215(19) Uani 1 1 d . . . . .
O1 O -0.3892(4) 0.34321(7) -0.3206(3) 0.0162(6) Uani 1 1 d . . . . .
O2 O -0.3793(5) 0.28716(7) -0.3224(4) 0.0191(6) Uani 1 1 d . . . . .
N1 N -0.0849(5) 0.31659(8) -0.2584(4) 0.0121(6) Uani 1 1 d . . . . .
N2 N 0.0009(5) 0.28991(8) -0.2667(4) 0.0152(7) Uani 1 1 d . . . . .
N3 N 0.1666(5) 0.29691(8) -0.2638(4) 0.0156(7) Uani 1 1 d . . . . .
N4 N 0.0372(6) 0.38498(9) -0.0766(4) 0.0183(7) Uani 1 1 d . . . . .
C1 C 0.1898(6) 0.32731(10) -0.2529(5) 0.0144(8) Uani 1 1 d . . . . .
H1 H 0.297384 0.337511 -0.249248 0.017 Uiso 1 1 calc R U . . .
C2 C 0.0307(5) 0.34056(9) -0.2482(4) 0.0108(7) Uani 1 1 d . . . . .
C3 C -0.0067(6) 0.37270(10) -0.2352(5) 0.0154(8) Uani 1 1 d . . . . .
H3 H -0.105091 0.382514 -0.315690 0.018 Uiso 1 1 calc R U . . .
C4 C 0.1471(6) 0.39078(9) -0.1429(5) 0.0142(8) Uani 1 1 d . . . . .
C5 C 0.3278(6) 0.40454(9) -0.1179(5) 0.0129(7) Uani 1 1 d . . . . .
C6 C 0.3975(6) 0.40608(9) -0.2308(5) 0.0149(8) Uani 1 1 d . . . . .
H6 H 0.328138 0.398521 -0.322238 0.018 Uiso 1 1 calc R U . . .
C7 C 0.5717(7) 0.41902(10) -0.2052(5) 0.0181(8) Uani 1 1 d . . . . .
H7 H 0.618819 0.420426 -0.279988 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6750(6) 0.42983(11) -0.0679(5) 0.0199(9) Uani 1 1 d . . . . .
H8 H 0.791130 0.438577 -0.051377 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6072(7) 0.42776(11) 0.0453(5) 0.0200(9) Uani 1 1 d . . . . .
H9 H 0.678263 0.434776 0.137478 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4338(6) 0.41524(10) 0.0198(5) 0.0163(8) Uani 1 1 d . . . . .
H10 H 0.387225 0.413919 0.094942 0.020 Uiso 1 1 calc R U . . .
C11 C -0.2798(6) 0.31464(10) -0.0730(5) 0.0134(7) Uani 1 1 d . . . . .
C12 C -0.2966(6) 0.34135(9) -0.0046(5) 0.0127(7) Uani 1 1 d . . . . .
H12 H -0.316659 0.359554 -0.054326 0.015 Uiso 1 1 calc R U . . .
C13 C -0.2828(6) 0.34007(10) 0.1398(5) 0.0159(8) Uani 1 1 d . . . . .
H13 H -0.295061 0.357610 0.187050 0.019 Uiso 1 1 calc R U . . .
C14 C -0.2506(6) 0.31265(10) 0.2153(5) 0.0158(8) Uani 1 1 d . . . . .
C15 C -0.2323(6) 0.28640(10) 0.1440(5) 0.0171(8) Uani 1 1 d . . . . .
H15 H -0.208744 0.268258 0.194294 0.020 Uiso 1 1 calc R U . . .
C16 C -0.2487(7) 0.28694(10) -0.0006(5) 0.0169(8) Uani 1 1 d . . . . .
H16 H -0.239296 0.269334 -0.048535 0.020 Uiso 1 1 calc R U . . .
C17 C -0.2385(7) 0.31158(12) 0.3718(5) 0.0216(9) Uani 1 1 d . . . . .
H17A H -0.169756 0.328699 0.422935 0.032 Uiso 1 1 calc R U . . .
H17B H -0.175816 0.293475 0.416478 0.032 Uiso 1 1 calc R U . . .
H17C H -0.362167 0.311877 0.375268 0.032 Uiso 1 1 calc R U . . .
S1' S 1.18615(14) 0.46278(2) 0.32440(10) 0.01009(18) Uani 1 1 d . . . . .
O1' O 1.0177(4) 0.45032(7) 0.2253(3) 0.0143(6) Uani 1 1 d . . . . .
O2' O 1.2739(4) 0.48788(6) 0.2857(3) 0.0138(6) Uani 1 1 d . . . . .
N1' N 1.3469(5) 0.43409(8) 0.3541(4) 0.0114(6) Uani 1 1 d . . . . .
N2' N 1.5322(5) 0.44180(8) 0.4013(4) 0.0146(7) Uani 1 1 d . . . . .
N3' N 1.6261(5) 0.41660(8) 0.4347(4) 0.0171(7) Uani 1 1 d . . . . .
N4' N 1.1243(6) 0.36699(8) 0.4474(4) 0.0177(7) Uani 1 1 d . . . . .
C1' C 1.5046(6) 0.39310(9) 0.4116(5) 0.0146(8) Uani 1 1 d . . . . .
H1' H 1.538713 0.372973 0.427543 0.018 Uiso 1 1 calc R U . . .
C2' C 1.3254(6) 0.40355(9) 0.3614(4) 0.0125(7) Uani 1 1 d . . . . .
C3' C 1.1486(6) 0.38674(9) 0.3220(5) 0.0138(8) Uani 1 1 d . . . . .
H3' H 1.037011 0.394829 0.246373 0.017 Uiso 1 1 calc R U . . .
C4' C 1.1631(6) 0.35428(9) 0.3473(5) 0.0141(8) Uani 1 1 d . . . . .
C5' C 1.2110(6) 0.32566(9) 0.2987(5) 0.0132(7) Uani 1 1 d . . . . .
C6' C 1.2318(6) 0.32403(9) 0.1643(5) 0.0148(8) Uani 1 1 d . . . . .
H6' H 1.212600 0.341019 0.105735 0.018 Uiso 1 1 calc R U . . .
C7' C 1.2814(7) 0.29696(10) 0.1180(5) 0.0183(8) Uani 1 1 d . . . . .
H7' H 1.297010 0.295757 0.028729 0.022 Uiso 1 1 calc R U . . .
C8' C 1.3076(6) 0.27169(10) 0.2058(5) 0.0176(8) Uani 1 1 d . . . . .
H8' H 1.339636 0.253474 0.174547 0.021 Uiso 1 1 calc R U . . .
C9' C 1.2863(7) 0.27339(10) 0.3399(5) 0.0177(8) Uani 1 1 d . . . . .
H9' H 1.304182 0.256309 0.397720 0.021 Uiso 1 1 calc R U . . .
C10' C 1.2389(6) 0.30027(10) 0.3879(5) 0.0161(8) Uani 1 1 d . . . . .
H10' H 1.225670 0.301474 0.478047 0.019 Uiso 1 1 calc R U . . .
C11' C 1.1711(5) 0.46788(8) 0.4958(4) 0.0098(7) Uani 1 1 d . . . . .
C12' C 1.0271(6) 0.45413(9) 0.5272(5) 0.0133(7) Uani 1 1 d . . . . .
H12' H 0.937910 0.442466 0.458406 0.016 Uiso 1 1 calc R U . . .
C13' C 1.0211(6) 0.45846(10) 0.6661(5) 0.0172(8) Uani 1 1 d . . . . .
H13' H 0.925220 0.449677 0.689526 0.021 Uiso 1 1 calc R U . . .
C14' C 1.1554(6) 0.47563(10) 0.7703(5) 0.0157(8) Uani 1 1 d . . . . .
C15' C 1.2968(7) 0.48917(10) 0.7331(5) 0.0186(8) Uani 1 1 d . . . . .
H15' H 1.385552 0.500988 0.801441 0.022 Uiso 1 1 calc R U . . .
C16' C 1.3076(6) 0.48537(10) 0.5967(5) 0.0153(8) Uani 1 1 d . . . . .
H16' H 1.403075 0.494228 0.573129 0.018 Uiso 1 1 calc R U . . .
C17' C 1.1485(8) 0.47966(11) 0.9204(5) 0.0237(10) Uani 1 1 d . . . . .
H17D H 1.221606 0.464240 0.983487 0.036 Uiso 1 1 calc R U . . .
H17E H 1.021293 0.478264 0.915614 0.036 Uiso 1 1 calc R U . . .
H17F H 1.198116 0.499028 0.957639 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.428(3) . ?
S1 O2 1.422(3) . ?
S1 N1 1.717(4) . ?
S1 C11 1.748(4) . ?
N1 N2 1.373(5) . ?
N1 C2 1.366(5) . ?
N2 N3 1.296(5) . ?
N3 C1 1.363(5) . ?
N4 C3 1.573(6) . ?
N4 C4 1.262(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.368(6) . ?
C2 C3 1.472(6) . ?
C3 H3 0.9800 . ?
C3 C4 1.448(6) . ?
C4 C5 1.451(6) . ?
C5 C6 1.395(6) . ?
C5 C10 1.393(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(6) . ?
C11 C16 1.401(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(6) . ?
C14 C15 1.395(6) . ?
C14 C17 1.511(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(6) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
S1' O1' 1.424(3) . ?
S1' O2' 1.422(3) . ?
S1' N1' 1.724(4) . ?
S1' C11' 1.747(4) . ?
N1' N2' 1.369(5) . ?
N1' C2' 1.373(5) . ?
N2' N3' 1.309(5) . ?
N3' C1' 1.363(5) . ?
N4' C3' 1.580(6) . ?
N4' C4' 1.260(6) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.364(6) . ?
C2' C3' 1.472(6) . ?
C3' H3' 0.9800 . ?
C3' C4' 1.462(6) . ?
C4' C5' 1.452(6) . ?
C5' C6' 1.390(6) . ?
C5' C10' 1.400(6) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.387(6) . ?
C7' H7' 0.9300 . ?
C7' C8' 1.388(6) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.389(6) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.381(6) . ?
C10' H10' 0.9300 . ?
C11' C12' 1.389(5) . ?
C11' C16' 1.394(6) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.398(6) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.393(7) . ?
C14' C15' 1.396(6) . ?
C14' C17' 1.509(6) . ?
C15' H15' 0.9300 . ?
C15' C16' 1.385(6) . ?
C16' H16' 0.9300 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 104.15(18) . . ?
O1 S1 C11 110.0(2) . . ?
O2 S1 O1 122.1(2) . . ?
O2 S1 N1 104.34(19) . . ?
O2 S1 C11 110.0(2) . . ?
N1 S1 C11 104.51(18) . . ?
N2 N1 S1 118.1(3) . . ?
C2 N1 S1 130.4(3) . . ?
C2 N1 N2 111.6(3) . . ?
N3 N2 N1 106.0(3) . . ?
N2 N3 C1 109.8(4) . . ?
C4 N4 C3 60.2(3) . . ?
N3 C1 H1 125.1 . . ?
N3 C1 C2 109.7(4) . . ?
C2 C1 H1 125.1 . . ?
N1 C2 C1 102.9(4) . . ?
N1 C2 C3 128.5(4) . . ?
C1 C2 C3 128.6(4) . . ?
N4 C3 H3 118.6 . . ?
C2 C3 N4 116.3(4) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 N4 49.2(3) . . ?
C4 C3 C2 117.0(4) . . ?
C4 C3 H3 118.6 . . ?
N4 C4 C3 70.6(3) . . ?
N4 C4 C5 140.3(4) . . ?
C3 C4 C5 148.6(4) . . ?
C6 C5 C4 119.8(4) . . ?
C10 C5 C4 119.9(4) . . ?
C10 C5 C6 120.3(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.3(4) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(4) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.3(4) . . ?
C9 C10 H10 119.9 . . ?
C12 C11 S1 119.3(3) . . ?
C12 C11 C16 122.1(4) . . ?
C16 C11 S1 118.6(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.2(4) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.9(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C17 120.2(4) . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 C17 120.4(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 120.8 . . ?
C15 C16 C11 118.4(4) . . ?
C15 C16 H16 120.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1' S1' N1' 104.24(18) . . ?
O1' S1' C11' 110.96(19) . . ?
O2' S1' O1' 121.38(19) . . ?
O2' S1' N1' 104.43(18) . . ?
O2' S1' C11' 110.90(18) . . ?
N1' S1' C11' 102.76(18) . . ?
N2' N1' S1' 117.6(3) . . ?
N2' N1' C2' 111.0(3) . . ?
C2' N1' S1' 130.5(3) . . ?
N3' N2' N1' 106.3(3) . . ?
N2' N3' C1' 109.4(4) . . ?
C4' N4' C3' 60.8(3) . . ?
N3' C1' H1' 125.1 . . ?
N3' C1' C2' 109.8(4) . . ?
C2' C1' H1' 125.1 . . ?
N1' C2' C3' 127.2(4) . . ?
C1' C2' N1' 103.4(4) . . ?
C1' C2' C3' 129.4(4) . . ?
N4' C3' H3' 119.0 . . ?
C2' C3' N4' 115.4(3) . . ?
C2' C3' H3' 119.0 . . ?
C4' C3' N4' 48.8(2) . . ?
C4' C3' C2' 116.7(4) . . ?
C4' C3' H3' 119.0 . . ?
N4' C4' C3' 70.5(3) . . ?
N4' C4' C5' 144.0(4) . . ?
C5' C4' C3' 145.2(4) . . ?
C6' C5' C4' 119.2(4) . . ?
C6' C5' C10' 120.8(4) . . ?
C10' C5' C4' 120.0(4) . . ?
C5' C6' H6' 120.1 . . ?
C7' C6' C5' 119.7(4) . . ?
C7' C6' H6' 120.1 . . ?
C6' C7' H7' 120.2 . . ?
C6' C7' C8' 119.6(4) . . ?
C8' C7' H7' 120.2 . . ?
C7' C8' H8' 119.7 . . ?
C7' C8' C9' 120.5(4) . . ?
C9' C8' H8' 119.7 . . ?
C8' C9' H9' 119.8 . . ?
C10' C9' C8' 120.5(4) . . ?
C10' C9' H9' 119.8 . . ?
C5' C10' H10' 120.6 . . ?
C9' C10' C5' 118.9(4) . . ?
C9' C10' H10' 120.6 . . ?
C12' C11' S1' 119.3(3) . . ?
C12' C11' C16' 122.6(4) . . ?
C16' C11' S1' 118.1(3) . . ?
C11' C12' H12' 121.2 . . ?
C11' C12' C13' 117.6(4) . . ?
C13' C12' H12' 121.2 . . ?
C12' C13' H13' 119.2 . . ?
C14' C13' C12' 121.5(4) . . ?
C14' C13' H13' 119.2 . . ?
C13' C14' C15' 118.8(4) . . ?
C13' C14' C17' 120.8(4) . . ?
C15' C14' C17' 120.4(4) . . ?
C14' C15' H15' 119.3 . . ?
C16' C15' C14' 121.4(4) . . ?
C16' C15' H15' 119.3 . . ?
C11' C16' H16' 121.0 . . ?
C15' C16' C11' 118.1(4) . . ?
C15' C16' H16' 121.0 . . ?
C14' C17' H17D 109.5 . . ?
C14' C17' H17E 109.5 . . ?
C14' C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 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
S1 N1 N2 N3 -179.1(3) . . . . ?
S1 N1 C2 C1 178.9(3) . . . . ?
S1 N1 C2 C3 -1.1(6) . . . . ?
S1 C11 C12 C13 176.8(3) . . . . ?
S1 C11 C16 C15 -177.9(3) . . . . ?
O1 S1 N1 N2 -151.6(3) . . . . ?
O1 S1 N1 C2 30.5(4) . . . . ?
O1 S1 C11 C12 -13.4(4) . . . . ?
O1 S1 C11 C16 163.8(3) . . . . ?
O2 S1 N1 N2 -22.5(3) . . . . ?
O2 S1 N1 C2 159.6(4) . . . . ?
O2 S1 C11 C12 -150.6(3) . . . . ?
O2 S1 C11 C16 26.6(4) . . . . ?
N1 S1 C11 C12 97.9(3) . . . . ?
N1 S1 C11 C16 -84.9(4) . . . . ?
N1 N2 N3 C1 0.4(5) . . . . ?
N1 C2 C3 N4 87.7(5) . . . . ?
N1 C2 C3 C4 143.2(4) . . . . ?
N2 N1 C2 C1 0.9(4) . . . . ?
N2 N1 C2 C3 -179.0(4) . . . . ?
N2 N3 C1 C2 0.2(5) . . . . ?
N3 C1 C2 N1 -0.7(5) . . . . ?
N3 C1 C2 C3 179.3(4) . . . . ?
N4 C3 C4 C5 171.6(8) . . . . ?
N4 C4 C5 C6 -179.8(5) . . . . ?
N4 C4 C5 C10 2.3(8) . . . . ?
C1 C2 C3 N4 -92.3(5) . . . . ?
C1 C2 C3 C4 -36.8(6) . . . . ?
C2 N1 N2 N3 -0.8(5) . . . . ?
C2 C3 C4 N4 -102.6(4) . . . . ?
C2 C3 C4 C5 69.0(9) . . . . ?
C3 N4 C4 C5 -173.2(7) . . . . ?
C3 C4 C5 C6 12.6(10) . . . . ?
C3 C4 C5 C10 -165.2(6) . . . . ?
C4 N4 C3 C2 103.9(4) . . . . ?
C4 C5 C6 C7 -179.3(4) . . . . ?
C4 C5 C10 C9 178.6(4) . . . . ?
C5 C6 C7 C8 0.9(7) . . . . ?
C6 C5 C10 C9 0.8(6) . . . . ?
C6 C7 C8 C9 0.4(7) . . . . ?
C7 C8 C9 C10 -1.0(7) . . . . ?
C8 C9 C10 C5 0.5(7) . . . . ?
C10 C5 C6 C7 -1.5(6) . . . . ?
C11 S1 N1 N2 92.9(3) . . . . ?
C11 S1 N1 C2 -84.9(4) . . . . ?
C11 C12 C13 C14 0.7(6) . . . . ?
C12 C11 C16 C15 -0.8(7) . . . . ?
C12 C13 C14 C15 0.0(7) . . . . ?
C12 C13 C14 C17 -179.2(4) . . . . ?
C13 C14 C15 C16 -1.1(7) . . . . ?
C14 C15 C16 C11 1.5(7) . . . . ?
C16 C11 C12 C13 -0.3(6) . . . . ?
C17 C14 C15 C16 178.0(4) . . . . ?
S1' N1' N2' N3' 171.6(3) . . . . ?
S1' N1' C2' C1' -169.9(3) . . . . ?
S1' N1' C2' C3' 10.7(6) . . . . ?
S1' C11' C12' C13' 179.3(3) . . . . ?
S1' C11' C16' C15' -179.4(3) . . . . ?
O1' S1' N1' N2' 157.2(3) . . . . ?
O1' S1' N1' C2' -34.8(4) . . . . ?
O1' S1' C11' C12' 13.9(4) . . . . ?
O1' S1' C11' C16' -167.2(3) . . . . ?
O2' S1' N1' N2' 28.9(3) . . . . ?
O2' S1' N1' C2' -163.1(4) . . . . ?
O2' S1' C11' C12' 151.9(3) . . . . ?
O2' S1' C11' C16' -29.1(4) . . . . ?
N1' S1' C11' C12' -97.0(3) . . . . ?
N1' S1' C11' C16' 81.9(3) . . . . ?
N1' N2' N3' C1' -0.8(5) . . . . ?
N1' C2' C3' N4' -122.0(4) . . . . ?
N1' C2' C3' C4' -176.7(4) . . . . ?
N2' N1' C2' C1' -1.4(5) . . . . ?
N2' N1' C2' C3' 179.3(4) . . . . ?
N2' N3' C1' C2' -0.1(5) . . . . ?
N3' C1' C2' N1' 0.9(5) . . . . ?
N3' C1' C2' C3' -179.8(4) . . . . ?
N4' C3' C4' C5' -173.9(8) . . . . ?
N4' C4' C5' C6' 176.5(6) . . . . ?
N4' C4' C5' C10' -4.6(9) . . . . ?
C1' C2' C3' N4' 58.8(6) . . . . ?
C1' C2' C3' C4' 4.1(7) . . . . ?
C2' N1' N2' N3' 1.4(5) . . . . ?
C2' C3' C4' N4' 101.4(4) . . . . ?
C2' C3' C4' C5' -72.5(8) . . . . ?
C3' N4' C4' C5' 174.1(8) . . . . ?
C3' C4' C5' C6' -13.3(9) . . . . ?
C3' C4' C5' C10' 165.5(6) . . . . ?
C4' N4' C3' C2' -104.2(4) . . . . ?
C4' C5' C6' C7' 178.6(4) . . . . ?
C4' C5' C10' C9' -179.3(4) . . . . ?
C5' C6' C7' C8' 0.7(7) . . . . ?
C6' C5' C10' C9' -0.4(7) . . . . ?
C6' C7' C8' C9' -0.6(7) . . . . ?
C7' C8' C9' C10' 0.0(7) . . . . ?
C8' C9' C10' C5' 0.6(7) . . . . ?
C10' C5' C6' C7' -0.2(7) . . . . ?
C11' S1' N1' N2' -87.0(3) . . . . ?
C11' S1' N1' C2' 81.0(4) . . . . ?
C11' C12' C13' C14' -0.7(6) . . . . ?
C12' C11' C16' C15' -0.4(6) . . . . ?
C12' C13' C14' C15' 1.2(7) . . . . ?
C12' C13' C14' C17' -179.0(4) . . . . ?
C13' C14' C15' C16' -1.2(7) . . . . ?
C14' C15' C16' C11' 0.9(7) . . . . ?
C16' C11' C12' C13' 0.3(6) . . . . ?
C17' C14' C15' C16' 178.9(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.806
####################################################################### 
# 
# 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_19485_lia036
_database_code_depnum_ccdc_archive 'CCDC 2167840'
loop_
_audit_author_name
_audit_author_address
"Dar'ya Spiridonova"
;St Petersburg University
Russia
;
_audit_update_record             
;
2022-04-21 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N4 O3 S'
_chemical_formula_sum            'C22 H20 N4 O3 S'
_chemical_formula_weight         420.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H20 N4 O3 S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.89270(10)
_cell_length_b                   17.0842(2)
_cell_length_c                   19.2068(2)
_cell_angle_alpha                111.2290(10)
_cell_angle_beta                 91.7750(10)
_cell_angle_gamma                99.4960(10)
_cell_volume                     2069.21(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15778
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.5530
_cell_measurement_theta_min      2.4610
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22886
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.995
_diffrn_reflns_theta_min         2.480
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  16.00   0.50    0.25    --   39.58 -87.00 127.00   88
  2  ω     22.00  57.00   0.50    0.25    --   39.58 -87.00 127.00   70
  3  ω     34.00  76.00   0.50    1.80    --  100.00 -87.00 127.00   84
  4  ω     90.00 118.00   0.50    1.80    --  100.00 -87.00 127.00   56
  5  ω    -84.00 -21.00   0.50    0.25    --  -39.58 -54.00 120.00  126
  6  ω    -12.00  28.00   0.50    0.25    --  -39.58  32.00  60.00   80
  7  ω     -8.00  18.00   0.50    0.25    --  -39.58  87.00-115.00   52
  8  ω    -48.00 -15.00   0.50    0.25    --  -39.58  32.00  60.00   66
  9  ω    -56.00 -18.00   0.50    0.25    --  -39.58 138.00 -90.00   76
 10  ω    -54.00  22.00   0.50    0.25    --  -39.58  43.00 -60.00  152
 11  ω    -68.00 -25.00   0.50    0.25    --  -39.58 -43.00 150.00   86
 12  ω   -104.00 -76.00   0.50    0.25    --  -39.58 -43.00 150.00   56
 13  ω     -4.00  21.00   0.50    0.25    --  -39.58  77.00 150.00   50
 14  ω    -44.00 -19.00   0.50    0.25    --  -39.58  77.00 150.00   50
 15  ω    -57.00 -16.00   0.50    0.25    --  -39.58  87.00-115.00   82
 16  ω    -89.00 -59.00   0.50    0.25    --  -39.58 138.00 -90.00   60
 17  ω     32.00  91.00   0.50    0.25    --   39.58  65.00  90.00  118
 18  ω     29.00  55.00   0.50    0.25    --   39.58 -54.00 -60.00   52
 19  ω     44.00  70.00   0.50    0.25    --   39.58-104.00  90.00   52
 20  ω    -24.00   3.00   0.50    0.25    --   39.58 -54.00 -60.00   54
 21  ω     17.00  96.00   0.50    0.25    --   39.58-138.00 120.00  158
 22  ω    -23.00  51.00   0.50    0.25    --   39.58 -32.00-150.00  148
 23  ω    -29.00   7.00   0.50    0.25    --   39.58 -89.00 -30.00   72
 24  ω     45.00  70.00   0.50    0.25    --   39.58 -89.00 -30.00   50
 25  ω     48.00 108.00   0.50    0.25    --   39.58  21.00  30.00  120
 26  ω    -10.00  17.00   0.50    0.25    --   39.58-104.00  90.00   54
 27  ω     72.00  98.00   0.50    0.25    --   39.58  43.00-120.00   52
 28  ω     57.00  82.00   0.50    0.25    --   39.58  32.00  60.00   50
 29  ω     43.00  69.00   0.50    0.25    --   39.58  43.00-120.00   52
 30  ω     36.00  81.00   0.50    1.80    --  100.00 -53.00  30.00   90
 31  ω     94.00 147.00   0.50    1.80    --  100.00 111.00 150.00  106
 32  ω     56.00 119.00   0.50    1.80    --  100.00 -69.00-150.00  126
 33  ω    102.00 129.00   0.50    1.80    --  100.00  22.00 -60.00   54
 34  ω     36.00 118.00   0.50    1.80    --  100.00-133.00  90.00  164
 35  ω     60.00 117.00   0.50    1.80    --  100.00 -61.00  30.00  114
 36  ω     79.00 108.00   0.50    1.80    --  100.00-111.00 -30.00   58
 37  ω     95.00 121.00   0.50    1.80    --  100.00 -86.00  60.00   52
 38  ω     33.00  78.00   0.50    1.80    --  100.00 -86.00  60.00   90
 39  ω     75.00 112.00   0.50    1.80    --  100.00 -37.00  30.00   74
 40  ω     34.00  70.00   0.50    1.80    --  100.00 -37.00  30.00   72
 41  ω     97.00 149.00   0.50    1.80    --  100.00  93.00 150.00  104
 42  ω    131.00 157.00   0.50    1.80    --  100.00  77.00-180.00   52
 43  ω     49.00  91.00   0.50    1.80    --  100.00-111.00   0.00   84
 44  ω     88.00 136.00   0.50    1.80    --  100.00 111.00-180.00   96
 45  ω     36.00 115.00   0.50    1.80    --  100.00 -45.00-150.00  158
 46  ω     47.00 107.00   0.50    1.80    --  100.00 -61.00 120.00  120
 47  ω     83.00 156.00   0.50    1.80    --  100.00  15.00 -90.00  146
 48  ω     78.00 104.00   0.50    1.80    --  100.00 -93.00-120.00   52
 49  ω     77.00 151.00   0.50    1.80    --  100.00  15.00-120.00  148
 50  ω     97.00 155.00   0.50    1.80    --  100.00  45.00 -30.00  116
 51  ω     61.00 106.00   0.50    1.80    --  100.00 -93.00  30.00   90
 52  ω    124.00 150.00   0.50    1.80    --  100.00 111.00 120.00   52
 53  ω     84.00 118.00   0.50    1.80    --  100.00-133.00 -60.00   68
 54  ω     39.00  65.00   0.50    1.80    --  100.00-133.00 -60.00   52
 55  ω     36.00 116.00   0.50    1.80    --  100.00 -45.00 120.00  160
 56  ω     91.00 116.00   0.50    1.80    --  100.00-133.00-150.00   50
 57  ω     30.00  56.00   0.50    1.80    --  100.00 -15.00   0.00   52
 58  ω     81.00 121.00   0.50    1.80    --  100.00 -15.00   0.00   80
 59  ω     97.00 122.00   0.50    1.80    --  100.00  30.00 150.00   50
 60  ω     45.00  70.00   0.50    1.80    --  100.00-133.00-150.00   50
 61  ω    123.00 148.00   0.50    1.80    --  100.00  30.00 120.00   50
 62  ω     69.00 118.00   0.50    1.80    --  100.00 -53.00 -90.00   98
 63  ω    111.00 155.00   0.50    1.80    --  100.00  93.00 -30.00   88
 64  ω     84.00 127.00   0.50    1.80    --  100.00  77.00 -30.00   86
 65  ω     75.00 108.00   0.50    1.80    --  100.00-111.00-180.00   66
 66  ω     39.00  66.00   0.50    1.80    --  100.00-111.00 -90.00   54
 67  ω     92.00 117.00   0.50    1.80    --  100.00  30.00 120.00   50
 68  ω     47.00  90.00   0.50    1.80    --  100.00 -93.00   0.00   86
 69  ω     96.00 121.00   0.50    1.80    --  100.00  30.00  90.00   50
 70  ω     84.00 157.00   0.50    1.80    --  100.00  53.00 -60.00  146
 71  ω     86.00 112.00   0.50    1.80    --  100.00 111.00 120.00   52
 72  ω    132.00 157.00   0.50    1.80    --  100.00  93.00-120.00   50
 73  ω     45.00  70.00   0.50    1.80    --  100.00 -93.00 150.00   50
 74  ω     88.00 117.00   0.50    1.80    --  100.00-133.00 150.00   58
 75  ω     85.00 111.00   0.50    1.80    --  100.00  87.00-115.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0238028000
_diffrn_orient_matrix_UB_12      0.0737796000
_diffrn_orient_matrix_UB_13      0.0770940000
_diffrn_orient_matrix_UB_21      -0.2213255000
_diffrn_orient_matrix_UB_22      -0.0243742000
_diffrn_orient_matrix_UB_23      0.0078377000
_diffrn_orient_matrix_UB_31      0.0480192000
_diffrn_orient_matrix_UB_32      -0.0605646000
_diffrn_orient_matrix_UB_33      0.0383690000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7023
_reflns_number_total             7834
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+1.1166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C1(H1), C4(H4A), C5(H5), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19),
  C20(H20), C21(H21), N4'(H4'), C1'(H1'), C4'(H4'A), C5'(H5'), C7'(H7'),
 C8'(H8'), C17'(H17'), C18'(H18'), C19'(H19'), C20'(H20'), C21'(H21')
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C9'(H9'A,H9'B,
 H9'C), C15'(H15D,H15E,H15F), C22'(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.40840(6) 0.59356(2) 0.82465(2) 0.02386(10) Uani 1 1 d . . . . .
O1 O 0.53937(19) 0.54783(8) 0.84502(7) 0.0308(3) Uani 1 1 d . . . . .
O2 O 0.2924(2) 0.64368(8) 0.87618(7) 0.0327(3) Uani 1 1 d . . . . .
O3 O -0.02026(18) 0.05909(7) 0.41416(7) 0.0279(3) Uani 1 1 d . . . . .
N1 N 0.2381(2) 0.51593(8) 0.75752(8) 0.0240(3) Uani 1 1 d . . . . .
N2 N 0.2740(2) 0.43776(8) 0.71653(7) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.0738(2) 0.53530(9) 0.73417(9) 0.0305(3) Uani 1 1 d . . . . .
N4 N 0.20084(19) 0.25907(8) 0.61699(7) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.293131 0.269717 0.653628 0.024 Uiso 1 1 calc R U . . .
C1 C -0.0057(3) 0.46491(11) 0.67682(10) 0.0290(4) Uani 1 1 d . . . . .
H1 H -0.126255 0.456757 0.647541 0.035 Uiso 1 1 calc R U . . .
C2 C 0.1173(2) 0.40348(10) 0.66584(9) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.5274(2) 0.65247(10) 0.77523(9) 0.0224(3) Uani 1 1 d . . . . .
C4 C 0.4368(2) 0.71289(10) 0.76106(9) 0.0245(3) Uani 1 1 d . . . . .
H4A H 0.310906 0.722022 0.777493 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5344(3) 0.75932(11) 0.72247(10) 0.0273(3) Uani 1 1 d . . . . .
H5 H 0.473834 0.800240 0.711620 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7209(3) 0.74691(11) 0.69917(10) 0.0295(4) Uani 1 1 d . . . . .
C7 C 0.8079(3) 0.68656(12) 0.71489(11) 0.0321(4) Uani 1 1 d . . . . .
H7 H 0.934879 0.678010 0.699397 0.039 Uiso 1 1 calc R U . . .
C8 C 0.7120(3) 0.63867(11) 0.75287(10) 0.0282(4) Uani 1 1 d . . . . .
H8 H 0.771614 0.597292 0.763331 0.034 Uiso 1 1 calc R U . . .
C9 C 0.8256(3) 0.79881(13) 0.65809(12) 0.0404(5) Uani 1 1 d . . . . .
H9A H 0.756581 0.781331 0.607926 0.061 Uiso 1 1 calc R U . . .
H9B H 0.961847 0.789332 0.653553 0.061 Uiso 1 1 calc R U . . .
H9C H 0.826697 0.859611 0.686020 0.061 Uiso 1 1 calc R U . . .
C10 C 0.0881(2) 0.31672(10) 0.61138(9) 0.0203(3) Uani 1 1 d . . . . .
C11 C -0.0405(2) 0.27693(10) 0.54694(9) 0.0203(3) Uani 1 1 d . . . . .
C12 C -0.0024(2) 0.19171(10) 0.51232(9) 0.0208(3) Uani 1 1 d . . . . .
C13 C 0.1488(2) 0.18394(10) 0.55804(9) 0.0205(3) Uani 1 1 d . . . . .
C14 C -0.0965(2) 0.12205(10) 0.44290(9) 0.0222(3) Uani 1 1 d . . . . .
C15 C -0.2891(3) 0.12672(12) 0.40735(10) 0.0306(4) Uani 1 1 d . . . . .
H15A H -0.272132 0.177489 0.394033 0.046 Uiso 1 1 calc R U . . .
H15B H -0.389577 0.130341 0.442830 0.046 Uiso 1 1 calc R U . . .
H15C H -0.331457 0.075370 0.361966 0.046 Uiso 1 1 calc R U . . .
C16 C -0.1778(2) 0.31974(10) 0.51865(9) 0.0217(3) Uani 1 1 d . . . . .
C17 C -0.3723(3) 0.31611(12) 0.53701(10) 0.0294(4) Uani 1 1 d . . . . .
H17 H -0.418294 0.286085 0.568181 0.035 Uiso 1 1 calc R U . . .
C18 C -0.4990(3) 0.35607(13) 0.51003(11) 0.0343(4) Uani 1 1 d . . . . .
H18 H -0.631074 0.353606 0.523098 0.041 Uiso 1 1 calc R U . . .
C19 C -0.4341(3) 0.39958(12) 0.46412(10) 0.0336(4) Uani 1 1 d . . . . .
H19 H -0.522157 0.425752 0.444756 0.040 Uiso 1 1 calc R U . . .
C20 C -0.2403(3) 0.40473(11) 0.44660(10) 0.0331(4) Uani 1 1 d . . . . .
H20 H -0.194590 0.435479 0.415961 0.040 Uiso 1 1 calc R U . . .
C21 C -0.1126(3) 0.36511(11) 0.47367(10) 0.0267(3) Uani 1 1 d . . . . .
H21 H 0.020233 0.368940 0.461441 0.032 Uiso 1 1 calc R U . . .
C22 C 0.2461(2) 0.11029(10) 0.55128(9) 0.0249(3) Uani 1 1 d . . . . .
H22A H 0.337203 0.103149 0.512207 0.037 Uiso 1 1 calc R U . . .
H22B H 0.145368 0.058154 0.537853 0.037 Uiso 1 1 calc R U . . .
H22C H 0.319800 0.121059 0.599317 0.037 Uiso 1 1 calc R U . . .
S1' S 1.61484(6) 0.01269(3) 0.81883(2) 0.02793(10) Uani 1 1 d . . . . .
O1' O 1.61874(19) -0.03126(8) 0.74028(7) 0.0323(3) Uani 1 1 d . . . . .
O2' O 1.79150(19) 0.04513(9) 0.86842(8) 0.0372(3) Uani 1 1 d . . . . .
O3' O 0.54980(17) 0.24092(7) 0.69015(7) 0.0272(3) Uani 1 1 d . . . . .
N1' N 1.5120(2) 0.09872(9) 0.82515(8) 0.0254(3) Uani 1 1 d . . . . .
N2' N 1.3624(2) 0.09045(9) 0.77355(8) 0.0246(3) Uani 1 1 d . . . . .
N3' N 1.5161(2) 0.16236(9) 0.89232(8) 0.0277(3) Uani 1 1 d . . . . .
N4' N 1.0036(2) 0.11081(8) 0.70644(7) 0.0220(3) Uani 1 1 d . . . . .
H4' H 1.039136 0.062175 0.680413 0.026 Uiso 1 1 calc R U . . .
C1' C 1.3722(3) 0.20038(11) 0.88228(10) 0.0265(3) Uani 1 1 d . . . . .
H1' H 1.338765 0.249921 0.918585 0.032 Uiso 1 1 calc R U . . .
C2' C 1.2741(2) 0.15566(10) 0.80839(9) 0.0223(3) Uani 1 1 d . . . . .
C3' C 1.4386(3) -0.04595(11) 0.85439(10) 0.0295(4) Uani 1 1 d . . . . .
C4' C 1.4985(3) -0.07187(12) 0.91110(10) 0.0350(4) Uani 1 1 d . . . . .
H4'A H 1.633046 -0.057374 0.931140 0.042 Uiso 1 1 calc R U . . .
C5' C 1.3589(3) -0.11913(12) 0.93786(11) 0.0397(5) Uani 1 1 d . . . . .
H5' H 1.399561 -0.138164 0.975743 0.048 Uiso 1 1 calc R U . . .
C6' C 1.1597(3) -0.13943(12) 0.91037(11) 0.0378(4) Uani 1 1 d . . . . .
C7' C 1.1045(3) -0.11273(12) 0.85336(12) 0.0377(4) Uani 1 1 d . . . . .
H7' H 0.969674 -0.126193 0.833871 0.045 Uiso 1 1 calc R U . . .
C8' C 1.2421(3) -0.06702(12) 0.82458(11) 0.0338(4) Uani 1 1 d . . . . .
H8' H 1.202911 -0.050284 0.785009 0.041 Uiso 1 1 calc R U . . .
C9' C 1.0093(4) -0.18921(15) 0.94115(13) 0.0517(6) Uani 1 1 d . . . . .
H9'A H 1.028470 -0.248559 0.924720 0.078 Uiso 1 1 calc R U . . .
H9'B H 0.876082 -0.187986 0.922687 0.078 Uiso 1 1 calc R U . . .
H9'C H 1.025158 -0.163536 0.996110 0.078 Uiso 1 1 calc R U . . .
C10' C 1.1035(2) 0.17093(10) 0.77291(9) 0.0216(3) Uani 1 1 d . . . . .
C11' C 1.0048(2) 0.23825(10) 0.79664(9) 0.0206(3) Uani 1 1 d . . . . .
C12' C 0.8386(2) 0.21795(10) 0.74204(9) 0.0205(3) Uani 1 1 d . . . . .
C13' C 0.8438(2) 0.13775(10) 0.68745(9) 0.0215(3) Uani 1 1 d . . . . .
C14' C 0.6917(2) 0.26965(10) 0.73882(9) 0.0211(3) Uani 1 1 d . . . . .
C15' C 0.7136(3) 0.35967(10) 0.79514(10) 0.0279(4) Uani 1 1 d . . . . .
H15D H 0.621606 0.389238 0.779024 0.042 Uiso 1 1 calc R U . . .
H15E H 0.849428 0.390108 0.798756 0.042 Uiso 1 1 calc R U . . .
H15F H 0.684177 0.358245 0.844304 0.042 Uiso 1 1 calc R U . . .
C16' C 1.0634(2) 0.31274(10) 0.86821(9) 0.0200(3) Uani 1 1 d . . . . .
C17' C 1.2149(2) 0.38010(10) 0.87315(9) 0.0234(3) Uani 1 1 d . . . . .
H17' H 1.276571 0.380117 0.829595 0.028 Uiso 1 1 calc R U . . .
C18' C 1.2762(3) 0.44718(11) 0.94136(10) 0.0274(4) Uani 1 1 d . . . . .
H18' H 1.378795 0.493123 0.944245 0.033 Uiso 1 1 calc R U . . .
C19' C 1.1880(3) 0.44729(11) 1.00526(9) 0.0279(4) Uani 1 1 d . . . . .
H19' H 1.231448 0.492862 1.052026 0.033 Uiso 1 1 calc R U . . .
C20' C 1.0368(3) 0.38100(11) 1.00085(9) 0.0280(4) Uani 1 1 d . . . . .
H20' H 0.975752 0.381332 1.044599 0.034 Uiso 1 1 calc R U . . .
C21' C 0.9740(2) 0.31401(11) 0.93279(9) 0.0249(3) Uani 1 1 d . . . . .
H21' H 0.869699 0.268762 0.930090 0.030 Uiso 1 1 calc R U . . .
C22' C 0.7073(3) 0.08320(11) 0.61939(9) 0.0271(3) Uani 1 1 d . . . . .
H22D H 0.762756 0.033011 0.591078 0.041 Uiso 1 1 calc R U . . .
H22E H 0.690555 0.116080 0.587818 0.041 Uiso 1 1 calc R U . . .
H22F H 0.578670 0.064583 0.634461 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4179(13) . ?
S1 O2 1.4188(13) . ?
S1 N1 1.7185(14) . ?
S1 C3 1.7477(16) . ?
O3 C14 1.230(2) . ?
N1 N2 1.3507(19) . ?
N1 N3 1.339(2) . ?
N2 C2 1.331(2) . ?
N3 C1 1.321(2) . ?
N4 H4 0.8800 . ?
N4 C10 1.3820(19) . ?
N4 C13 1.352(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.417(2) . ?
C2 C10 1.448(2) . ?
C3 C4 1.391(2) . ?
C3 C8 1.385(2) . ?
C4 H4A 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(3) . ?
C6 C7 1.390(3) . ?
C6 C9 1.503(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.380(2) . ?
C11 C12 1.438(2) . ?
C11 C16 1.486(2) . ?
C12 C13 1.396(2) . ?
C12 C14 1.469(2) . ?
C13 C22 1.488(2) . ?
C14 C15 1.501(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.394(2) . ?
C16 C21 1.394(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S1' O1' 1.4245(14) . ?
S1' O2' 1.4214(13) . ?
S1' N1' 1.7021(14) . ?
S1' C3' 1.7582(19) . ?
O3' C14' 1.235(2) . ?
N1' N2' 1.3613(19) . ?
N1' N3' 1.349(2) . ?
N2' C2' 1.330(2) . ?
N3' C1' 1.317(2) . ?
N4' H4' 0.8800 . ?
N4' C10' 1.386(2) . ?
N4' C13' 1.350(2) . ?
C1' H1' 0.9500 . ?
C1' C2' 1.428(2) . ?
C2' C10' 1.447(2) . ?
C3' C4' 1.391(3) . ?
C3' C8' 1.390(3) . ?
C4' H4'A 0.9500 . ?
C4' C5' 1.384(3) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.397(3) . ?
C6' C7' 1.395(3) . ?
C6' C9' 1.503(3) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.384(3) . ?
C8' H8' 0.9500 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10' C11' 1.375(2) . ?
C11' C12' 1.437(2) . ?
C11' C16' 1.484(2) . ?
C12' C13' 1.399(2) . ?
C12' C14' 1.462(2) . ?
C13' C22' 1.488(2) . ?
C14' C15' 1.505(2) . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' C17' 1.393(2) . ?
C16' C21' 1.397(2) . ?
C17' H17' 0.9500 . ?
C17' C18' 1.388(2) . ?
C18' H18' 0.9500 . ?
C18' C19' 1.386(3) . ?
C19' H19' 0.9500 . ?
C19' C20' 1.383(3) . ?
C20' H20' 0.9500 . ?
C20' C21' 1.387(2) . ?
C21' H21' 0.9500 . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 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
O1 S1 O2 122.92(8) . . ?
O1 S1 N1 104.45(7) . . ?
O1 S1 C3 110.20(8) . . ?
O2 S1 N1 104.33(8) . . ?
O2 S1 C3 109.60(8) . . ?
N1 S1 C3 103.22(7) . . ?
N2 N1 S1 123.21(11) . . ?
N3 N1 S1 120.35(11) . . ?
N3 N1 N2 115.51(13) . . ?
C2 N2 N1 103.20(13) . . ?
C1 N3 N1 103.47(13) . . ?
C10 N4 H4 124.9 . . ?
C13 N4 H4 124.9 . . ?
C13 N4 C10 110.18(13) . . ?
N3 C1 H1 125.4 . . ?
N3 C1 C2 109.28(15) . . ?
C2 C1 H1 125.4 . . ?
N2 C2 C1 108.46(14) . . ?
N2 C2 C10 122.47(14) . . ?
C1 C2 C10 129.06(15) . . ?
C4 C3 S1 119.33(13) . . ?
C8 C3 S1 118.60(13) . . ?
C8 C3 C4 122.05(16) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 C3 118.36(15) . . ?
C5 C4 H4A 120.8 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.94(16) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C9 120.10(17) . . ?
C7 C6 C5 119.15(16) . . ?
C7 C6 C9 120.75(17) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 120.93(16) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 118.56(16) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C2 121.93(14) . . ?
C11 C10 N4 108.08(13) . . ?
C11 C10 C2 129.95(14) . . ?
C10 C11 C12 106.74(13) . . ?
C10 C11 C16 124.37(14) . . ?
C12 C11 C16 128.72(14) . . ?
C11 C12 C14 129.82(14) . . ?
C13 C12 C11 106.95(14) . . ?
C13 C12 C14 123.23(14) . . ?
N4 C13 C12 108.04(13) . . ?
N4 C13 C22 120.96(14) . . ?
C12 C13 C22 130.99(14) . . ?
O3 C14 C12 120.50(14) . . ?
O3 C14 C15 119.56(15) . . ?
C12 C14 C15 119.94(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C11 120.95(14) . . ?
C21 C16 C11 120.18(14) . . ?
C21 C16 C17 118.86(15) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.37(16) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.37(17) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.66(16) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.21(17) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.50(16) . . ?
C20 C21 H21 119.7 . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1' S1' N1' 104.26(7) . . ?
O1' S1' C3' 110.47(8) . . ?
O2' S1' O1' 121.37(8) . . ?
O2' S1' N1' 106.28(7) . . ?
O2' S1' C3' 109.96(9) . . ?
N1' S1' C3' 102.56(8) . . ?
N2' N1' S1' 119.83(11) . . ?
N3' N1' S1' 120.03(11) . . ?
N3' N1' N2' 115.04(13) . . ?
C2' N2' N1' 103.39(13) . . ?
C1' N3' N1' 103.57(13) . . ?
C10' N4' H4' 124.9 . . ?
C13' N4' H4' 124.9 . . ?
C13' N4' C10' 110.10(13) . . ?
N3' C1' H1' 125.2 . . ?
N3' C1' C2' 109.52(15) . . ?
C2' C1' H1' 125.2 . . ?
N2' C2' C1' 108.31(14) . . ?
N2' C2' C10' 121.85(14) . . ?
C1' C2' C10' 129.80(15) . . ?
C4' C3' S1' 119.44(15) . . ?
C8' C3' S1' 119.59(14) . . ?
C8' C3' C4' 120.96(18) . . ?
C3' C4' H4'A 120.5 . . ?
C5' C4' C3' 118.93(19) . . ?
C5' C4' H4'A 120.5 . . ?
C4' C5' H5' 119.3 . . ?
C4' C5' C6' 121.43(17) . . ?
C6' C5' H5' 119.3 . . ?
C5' C6' C9' 120.79(19) . . ?
C7' C6' C5' 118.21(19) . . ?
C7' C6' C9' 121.0(2) . . ?
C6' C7' H7' 119.3 . . ?
C8' C7' C6' 121.4(2) . . ?
C8' C7' H7' 119.3 . . ?
C3' C8' H8' 120.5 . . ?
C7' C8' C3' 119.06(17) . . ?
C7' C8' H8' 120.5 . . ?
C6' C9' H9'A 109.5 . . ?
C6' C9' H9'B 109.5 . . ?
C6' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
N4' C10' C2' 121.50(14) . . ?
C11' C10' N4' 108.18(13) . . ?
C11' C10' C2' 130.20(15) . . ?
C10' C11' C12' 106.75(14) . . ?
C10' C11' C16' 123.35(14) . . ?
C12' C11' C16' 129.81(14) . . ?
C11' C12' C14' 128.91(14) . . ?
C13' C12' C11' 107.03(13) . . ?
C13' C12' C14' 124.01(14) . . ?
N4' C13' C12' 107.93(14) . . ?
N4' C13' C22' 120.71(14) . . ?
C12' C13' C22' 131.34(14) . . ?
O3' C14' C12' 121.06(14) . . ?
O3' C14' C15' 119.08(14) . . ?
C12' C14' C15' 119.85(14) . . ?
C14' C15' H15D 109.5 . . ?
C14' C15' H15E 109.5 . . ?
C14' C15' H15F 109.5 . . ?
H15D C15' H15E 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C17' C16' C11' 120.81(14) . . ?
C17' C16' C21' 119.00(15) . . ?
C21' C16' C11' 120.10(14) . . ?
C16' C17' H17' 119.8 . . ?
C18' C17' C16' 120.35(15) . . ?
C18' C17' H17' 119.8 . . ?
C17' C18' H18' 119.9 . . ?
C19' C18' C17' 120.18(15) . . ?
C19' C18' H18' 119.9 . . ?
C18' C19' H19' 120.0 . . ?
C20' C19' C18' 119.91(16) . . ?
C20' C19' H19' 120.0 . . ?
C19' C20' H20' 119.9 . . ?
C19' C20' C21' 120.24(16) . . ?
C21' C20' H20' 119.9 . . ?
C16' C21' H21' 119.8 . . ?
C20' C21' C16' 120.32(15) . . ?
C20' C21' H21' 119.8 . . ?
C13' C22' H22D 109.5 . . ?
C13' C22' H22E 109.5 . . ?
C13' C22' H22F 109.5 . . ?
H22D C22' H22E 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 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
S1 N1 N2 C2 -171.95(11) . . . . ?
S1 N1 N3 C1 171.76(12) . . . . ?
S1 C3 C4 C5 179.42(12) . . . . ?
S1 C3 C8 C7 -178.82(13) . . . . ?
O1 S1 N1 N2 -22.18(14) . . . . ?
O1 S1 N1 N3 169.41(13) . . . . ?
O1 S1 C3 C4 -169.22(13) . . . . ?
O1 S1 C3 C8 9.31(16) . . . . ?
O2 S1 N1 N2 -152.35(13) . . . . ?
O2 S1 N1 N3 39.24(15) . . . . ?
O2 S1 C3 C4 -31.00(16) . . . . ?
O2 S1 C3 C8 147.53(13) . . . . ?
N1 S1 C3 C4 79.71(14) . . . . ?
N1 S1 C3 C8 -101.76(14) . . . . ?
N1 N2 C2 C1 2.21(17) . . . . ?
N1 N2 C2 C10 -176.92(14) . . . . ?
N1 N3 C1 C2 -0.89(19) . . . . ?
N2 N1 N3 C1 2.49(19) . . . . ?
N2 C2 C10 N4 12.0(2) . . . . ?
N2 C2 C10 C11 -165.69(16) . . . . ?
N3 N1 N2 C2 -3.03(18) . . . . ?
N3 C1 C2 N2 -0.9(2) . . . . ?
N3 C1 C2 C10 178.17(16) . . . . ?
N4 C10 C11 C12 -0.22(17) . . . . ?
N4 C10 C11 C16 -175.93(14) . . . . ?
C1 C2 C10 N4 -166.91(16) . . . . ?
C1 C2 C10 C11 15.4(3) . . . . ?
C2 C10 C11 C12 177.74(15) . . . . ?
C2 C10 C11 C16 2.0(3) . . . . ?
C3 S1 N1 N2 93.08(13) . . . . ?
C3 S1 N1 N3 -75.33(14) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C9 -179.26(17) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C3 -0.3(3) . . . . ?
C8 C3 C4 C5 0.9(2) . . . . ?
C9 C6 C7 C8 179.89(17) . . . . ?
C10 N4 C13 C12 -0.20(17) . . . . ?
C10 N4 C13 C22 -179.00(14) . . . . ?
C10 C11 C12 C13 0.10(17) . . . . ?
C10 C11 C12 C14 179.87(15) . . . . ?
C10 C11 C16 C17 -94.0(2) . . . . ?
C10 C11 C16 C21 85.4(2) . . . . ?
C11 C12 C13 N4 0.06(17) . . . . ?
C11 C12 C13 C22 178.69(16) . . . . ?
C11 C12 C14 O3 165.91(16) . . . . ?
C11 C12 C14 C15 -15.2(2) . . . . ?
C11 C16 C17 C18 -179.77(16) . . . . ?
C11 C16 C21 C20 179.53(15) . . . . ?
C12 C11 C16 C17 91.3(2) . . . . ?
C12 C11 C16 C21 -89.3(2) . . . . ?
C13 N4 C10 C2 -177.89(14) . . . . ?
C13 N4 C10 C11 0.27(17) . . . . ?
C13 C12 C14 O3 -14.3(2) . . . . ?
C13 C12 C14 C15 164.51(15) . . . . ?
C14 C12 C13 N4 -179.73(14) . . . . ?
C14 C12 C13 C22 -1.1(3) . . . . ?
C16 C11 C12 C13 175.56(15) . . . . ?
C16 C11 C12 C14 -4.7(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C16 C21 C20 -1.1(3) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
C18 C19 C20 C21 1.3(3) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C21 C16 C17 C18 0.9(3) . . . . ?
S1' N1' N2' C2' 158.64(12) . . . . ?
S1' N1' N3' C1' -158.99(12) . . . . ?
S1' C3' C4' C5' -179.02(14) . . . . ?
S1' C3' C8' C7' -179.59(15) . . . . ?
O1' S1' N1' N2' 37.71(14) . . . . ?
O1' S1' N1' N3' -168.79(13) . . . . ?
O1' S1' C3' C4' 121.03(15) . . . . ?
O1' S1' C3' C8' -57.85(17) . . . . ?
O2' S1' N1' N2' 167.05(12) . . . . ?
O2' S1' N1' N3' -39.46(15) . . . . ?
O2' S1' C3' C4' -15.59(17) . . . . ?
O2' S1' C3' C8' 165.53(14) . . . . ?
N1' S1' C3' C4' -128.33(15) . . . . ?
N1' S1' C3' C8' 52.79(16) . . . . ?
N1' N2' C2' C1' -1.80(17) . . . . ?
N1' N2' C2' C10' -179.81(14) . . . . ?
N1' N3' C1' C2' 2.84(18) . . . . ?
N2' N1' N3' C1' -4.29(19) . . . . ?
N2' C2' C10' N4' 11.1(2) . . . . ?
N2' C2' C10' C11' -173.21(16) . . . . ?
N3' N1' N2' C2' 3.88(18) . . . . ?
N3' C1' C2' N2' -0.7(2) . . . . ?
N3' C1' C2' C10' 177.12(16) . . . . ?
N4' C10' C11' C12' -0.16(17) . . . . ?
N4' C10' C11' C16' 176.73(14) . . . . ?
C1' C2' C10' N4' -166.42(16) . . . . ?
C1' C2' C10' C11' 9.2(3) . . . . ?
C2' C10' C11' C12' -176.27(16) . . . . ?
C2' C10' C11' C16' 0.6(3) . . . . ?
C3' S1' N1' N2' -77.52(14) . . . . ?
C3' S1' N1' N3' 75.97(14) . . . . ?
C3' C4' C5' C6' -1.5(3) . . . . ?
C4' C3' C8' C7' 1.5(3) . . . . ?
C4' C5' C6' C7' 1.7(3) . . . . ?
C4' C5' C6' C9' -178.70(19) . . . . ?
C5' C6' C7' C8' -0.2(3) . . . . ?
C6' C7' C8' C3' -1.3(3) . . . . ?
C8' C3' C4' C5' -0.2(3) . . . . ?
C9' C6' C7' C8' -179.86(19) . . . . ?
C10' N4' C13' C12' 0.67(18) . . . . ?
C10' N4' C13' C22' -177.94(14) . . . . ?
C10' C11' C12' C13' 0.55(18) . . . . ?
C10' C11' C12' C14' -176.91(15) . . . . ?
C10' C11' C16' C17' 81.9(2) . . . . ?
C10' C11' C16' C21' -94.70(19) . . . . ?
C11' C12' C13' N4' -0.75(18) . . . . ?
C11' C12' C13' C22' 177.65(17) . . . . ?
C11' C12' C14' O3' -175.77(15) . . . . ?
C11' C12' C14' C15' 4.7(2) . . . . ?
C11' C16' C17' C18' -176.36(15) . . . . ?
C11' C16' C21' C20' 176.00(15) . . . . ?
C12' C11' C16' C17' -102.0(2) . . . . ?
C12' C11' C16' C21' 81.4(2) . . . . ?
C13' N4' C10' C2' 176.20(15) . . . . ?
C13' N4' C10' C11' -0.31(18) . . . . ?
C13' C12' C14' O3' 7.2(2) . . . . ?
C13' C12' C14' C15' -172.36(15) . . . . ?
C14' C12' C13' N4' 176.87(14) . . . . ?
C14' C12' C13' C22' -4.7(3) . . . . ?
C16' C11' C12' C13' -176.06(15) . . . . ?
C16' C11' C12' C14' 6.5(3) . . . . ?
C16' C17' C18' C19' 0.5(2) . . . . ?
C17' C16' C21' C20' -0.6(2) . . . . ?
C17' C18' C19' C20' -0.9(3) . . . . ?
C18' C19' C20' C21' 0.5(3) . . . . ?
C19' C20' C21' C16' 0.3(3) . . . . ?
C21' C16' C17' C18' 0.2(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.749
