# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_exp_1047
_database_code_depnum_ccdc_archive 'CCDC 2163811'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-08-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Cl N5 O S'
_chemical_formula_sum            'C14 H10 Cl N5 O S'
_chemical_formula_weight         331.78
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.0095(12)
_cell_length_b                   9.0931(5)
_cell_length_c                   14.1600(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.568(11)
_cell_angle_gamma                90
_cell_volume                     1457.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2661
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.7150
_cell_measurement_theta_min      3.7880
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10653
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.904
_diffrn_reflns_theta_min         3.601
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  -8.00   1.00   15.00    --   22.67 -87.00 -81.00   26
  2  ω    -27.00  -1.00   1.00   15.00    --  -24.24 -87.00 -81.00   26
  3  ω    -60.00  39.00   1.00   15.00    --  -24.24  87.00  36.00   99
  4  ω     54.00  99.00   1.00   15.00    --   22.67 178.00-120.00   45
  5  ω    -47.00  53.00   1.00   15.00    --   22.67 -77.00-150.00  100
  6  ω      9.00  58.00   1.00   15.00    --   22.67 -87.00 -81.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0273711000
_diffrn_orient_matrix_UB_12      0.0642161000
_diffrn_orient_matrix_UB_13      -0.0103083000
_diffrn_orient_matrix_UB_21      0.0559332000
_diffrn_orient_matrix_UB_22      -0.0270120000
_diffrn_orient_matrix_UB_23      0.0304222000
_diffrn_orient_matrix_UB_31      0.0070920000
_diffrn_orient_matrix_UB_32      -0.0349948000
_diffrn_orient_matrix_UB_33      -0.0424190000
_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                2459
_reflns_number_total             3948
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.089
_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)+(0.1200P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.2286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_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 0.13269(10) 0.41070(8) 0.25578(5) 0.0628(3) Uani 1 1 d . . . . .
Cl1 Cl 0.57739(10) 0.63042(15) 0.34112(9) 0.0976(4) Uani 1 1 d . . . . .
O1 O 0.1195(2) 0.23842(19) 0.57394(14) 0.0523(5) Uani 1 1 d . . . . .
N4 N 0.1319(2) 0.3451(2) 0.43038(15) 0.0391(5) Uani 1 1 d . . . . .
N9 N 0.1601(2) 0.7388(2) 0.55608(17) 0.0423(5) Uani 1 1 d . . . . .
N7 N 0.1479(2) 0.5528(2) 0.65669(16) 0.0439(5) Uani 1 1 d . . . . .
N11 N 0.1486(2) 0.6031(2) 0.40447(17) 0.0451(6) Uani 1 1 d . . . . .
N3 N 0.1213(2) 0.2113(2) 0.38192(17) 0.0486(6) Uani 1 1 d . . . . .
C10 C 0.1515(2) 0.6125(3) 0.50140(19) 0.0375(5) Uani 1 1 d . . . . .
C6 C 0.1436(2) 0.4986(3) 0.56394(18) 0.0373(5) Uani 1 1 d . . . . .
C5 C 0.1312(2) 0.3506(3) 0.53091(18) 0.0385(5) Uani 1 1 d . . . . .
C8 C 0.1576(3) 0.6945(3) 0.6479(2) 0.0458(6) Uani 1 1 d . . . . .
C12 C 0.1388(3) 0.4676(3) 0.37442(19) 0.0440(6) Uani 1 1 d . . . . .
C13 C 0.1672(3) 0.8898(3) 0.5229(2) 0.0498(7) Uani 1 1 d . . . . .
H13A H 0.119940 0.953173 0.549720 0.060 Uiso 1 1 calc R U . . .
H13B H 0.134174 0.893851 0.450400 0.060 Uiso 1 1 calc R U . . .
C2 C 0.1214(3) 0.2318(3) 0.2922(2) 0.0548(8) Uani 1 1 d . . . . .
C15 C 0.3691(3) 0.8699(3) 0.5056(2) 0.0519(7) Uani 1 1 d . . . . .
C14 C 0.2943(3) 0.9474(3) 0.5566(2) 0.0563(8) Uani 1 1 d . . . . .
H14A H 0.293157 1.051794 0.542287 0.068 Uiso 1 1 calc R U . . .
H14B H 0.329646 0.934744 0.628535 0.068 Uiso 1 1 calc R U . . .
C19 C 0.4178(3) 0.8278(4) 0.3563(3) 0.0647(9) Uani 1 1 d . . . . .
H19 H 0.406684 0.849715 0.289649 0.078 Uiso 1 1 calc R U . . .
C20 C 0.3534(3) 0.8993(3) 0.4056(3) 0.0607(8) Uani 1 1 d . . . . .
H20 H 0.297917 0.969081 0.371538 0.073 Uiso 1 1 calc R U . . .
C18 C 0.4989(3) 0.7237(4) 0.4057(3) 0.0616(8) Uani 1 1 d . . . . .
C16 C 0.4531(3) 0.7664(4) 0.5543(2) 0.0649(9) Uani 1 1 d . . . . .
H16 H 0.465777 0.745467 0.621409 0.078 Uiso 1 1 calc R U . . .
C17 C 0.5186(3) 0.6936(4) 0.5048(3) 0.0740(10) Uani 1 1 d . . . . .
H17 H 0.575366 0.624887 0.538547 0.089 Uiso 1 1 calc R U . . .
H2 H 0.119(3) 0.143(4) 0.250(3) 0.063(10) Uiso 1 1 d . . . . .
H8 H 0.160(2) 0.770(3) 0.704(2) 0.048(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.736(3) . ?
S1 C2 1.725(3) . ?
Cl1 C18 1.739(4) . ?
O1 C5 1.220(3) . ?
N4 N3 1.382(3) . ?
N4 C5 1.427(3) . ?
N4 C12 1.386(3) . ?
N9 C10 1.369(3) . ?
N9 C8 1.371(3) . ?
N9 C13 1.463(3) . ?
N7 C6 1.388(3) . ?
N7 C8 1.303(3) . ?
N11 C10 1.364(3) . ?
N11 C12 1.296(3) . ?
N3 C2 1.285(4) . ?
C10 C6 1.386(3) . ?
C6 C5 1.416(3) . ?
C8 H8 1.04(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.531(4) . ?
C2 H2 1.00(4) . ?
C15 C14 1.504(5) . ?
C15 C20 1.390(4) . ?
C15 C16 1.382(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C20 1.367(5) . ?
C19 C18 1.370(5) . ?
C20 H20 0.9300 . ?
C18 C17 1.370(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C12 88.52(13) . . ?
N3 N4 C5 119.73(18) . . ?
N3 N4 C12 115.9(2) . . ?
C12 N4 C5 124.3(2) . . ?
C10 N9 C8 105.5(2) . . ?
C10 N9 C13 127.4(2) . . ?
C8 N9 C13 127.0(2) . . ?
C8 N7 C6 103.7(2) . . ?
C12 N11 C10 111.0(2) . . ?
C2 N3 N4 109.4(2) . . ?
N9 C10 C6 105.9(2) . . ?
N11 C10 N9 126.4(2) . . ?
N11 C10 C6 127.7(2) . . ?
N7 C6 C5 128.1(2) . . ?
C10 C6 N7 110.5(2) . . ?
C10 C6 C5 121.4(2) . . ?
O1 C5 N4 120.6(2) . . ?
O1 C5 C6 130.3(2) . . ?
C6 C5 N4 109.12(19) . . ?
N9 C8 H8 121.6(17) . . ?
N7 C8 N9 114.4(2) . . ?
N7 C8 H8 124.0(17) . . ?
N4 C12 S1 108.82(18) . . ?
N11 C12 S1 124.82(19) . . ?
N11 C12 N4 126.4(2) . . ?
N9 C13 H13A 109.1 . . ?
N9 C13 H13B 109.1 . . ?
N9 C13 C14 112.3(2) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
S1 C2 H2 125(2) . . ?
N3 C2 S1 117.3(2) . . ?
N3 C2 H2 117(2) . . ?
C20 C15 C14 120.0(3) . . ?
C16 C15 C14 122.2(3) . . ?
C16 C15 C20 117.8(3) . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 C13 112.6(2) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C20 C19 H19 120.2 . . ?
C20 C19 C18 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C15 C20 H20 119.3 . . ?
C19 C20 C15 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C19 C18 Cl1 119.1(3) . . ?
C19 C18 C17 120.7(3) . . ?
C17 C18 Cl1 120.2(3) . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C17 C16 -178.4(3) . . . . ?
N4 N3 C2 S1 -0.5(4) . . . . ?
N9 C10 C6 N7 -0.3(3) . . . . ?
N9 C10 C6 C5 178.8(2) . . . . ?
N9 C13 C14 C15 67.7(3) . . . . ?
N7 C6 C5 O1 1.4(5) . . . . ?
N7 C6 C5 N4 -179.6(2) . . . . ?
N11 C10 C6 N7 -179.0(2) . . . . ?
N11 C10 C6 C5 0.2(4) . . . . ?
N3 N4 C5 O1 -1.1(4) . . . . ?
N3 N4 C5 C6 179.8(2) . . . . ?
N3 N4 C12 S1 -0.4(3) . . . . ?
N3 N4 C12 N11 179.8(3) . . . . ?
C10 N9 C8 N7 -0.2(3) . . . . ?
C10 N9 C13 C14 -98.7(3) . . . . ?
C10 N11 C12 S1 -179.8(2) . . . . ?
C10 N11 C12 N4 -0.1(4) . . . . ?
C10 C6 C5 O1 -177.5(3) . . . . ?
C10 C6 C5 N4 1.4(3) . . . . ?
C6 N7 C8 N9 0.0(3) . . . . ?
C5 N4 N3 C2 178.6(3) . . . . ?
C5 N4 C12 S1 -178.3(2) . . . . ?
C5 N4 C12 N11 1.9(4) . . . . ?
C8 N9 C10 N11 178.9(3) . . . . ?
C8 N9 C10 C6 0.3(3) . . . . ?
C8 N9 C13 C14 83.3(3) . . . . ?
C8 N7 C6 C10 0.2(3) . . . . ?
C8 N7 C6 C5 -178.8(3) . . . . ?
C12 S1 C2 N3 0.3(3) . . . . ?
C12 N4 N3 C2 0.6(4) . . . . ?
C12 N4 C5 O1 176.7(3) . . . . ?
C12 N4 C5 C6 -2.4(3) . . . . ?
C12 N11 C10 N9 -179.3(3) . . . . ?
C12 N11 C10 C6 -1.0(4) . . . . ?
C13 N9 C10 N11 0.6(4) . . . . ?
C13 N9 C10 C6 -178.1(3) . . . . ?
C13 N9 C8 N7 178.2(3) . . . . ?
C2 S1 C12 N4 0.1(2) . . . . ?
C2 S1 C12 N11 179.9(3) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C14 C15 C20 C19 -178.2(3) . . . . ?
C14 C15 C16 C17 178.1(3) . . . . ?
C19 C18 C17 C16 1.9(6) . . . . ?
C20 C15 C14 C13 73.7(4) . . . . ?
C20 C15 C16 C17 -0.6(5) . . . . ?
C20 C19 C18 Cl1 178.4(3) . . . . ?
C20 C19 C18 C17 -2.0(6) . . . . ?
C18 C19 C20 C15 0.7(6) . . . . ?
C16 C15 C14 C13 -105.0(4) . . . . ?
C16 C15 C20 C19 0.5(5) . . . . ?


_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 1.260
_oxdiff_exptl_absorpt_empirical_full_min 0.812
####################################################################### 
# 
# 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_exp_1046
_database_code_depnum_ccdc_archive 'CCDC 2163812'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-08-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 N8 O2 S2, 2(C2 H6 O S)'
_chemical_formula_sum            'C22 H34 N8 O4 S4'
_chemical_formula_weight         602.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8823(13)
_cell_length_b                   16.0031(17)
_cell_length_c                   16.3570(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3110.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1327
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      21.9050
_cell_measurement_theta_min      4.1650
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11768
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.869
_diffrn_reflns_theta_min         3.562
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  26.00   1.00   20.00    --   22.52  91.00  72.00   29
  2  ω      9.00  64.00   1.00   20.00    --   22.52  54.00-151.00   55
  3  ω    -35.00  29.00   1.00   20.00    --  -24.08  81.00 -28.00   64
  4  ω     39.00  76.00   1.00   20.00    --   22.52 178.00-180.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0524538000
_diffrn_orient_matrix_UB_12      -0.0211319000
_diffrn_orient_matrix_UB_13      0.0001213000
_diffrn_orient_matrix_UB_21      -0.0144746000
_diffrn_orient_matrix_UB_22      0.0196492000
_diffrn_orient_matrix_UB_23      -0.0374501000
_diffrn_orient_matrix_UB_31      0.0244569000
_diffrn_orient_matrix_UB_32      -0.0336391000
_diffrn_orient_matrix_UB_33      -0.0219187000
_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                1507
_reflns_number_total             4251
_reflns_odcompleteness_completeness 98.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0045(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.2165
_refine_ls_R_factor_gt           0.0889
_refine_ls_restrained_S_all      1.111
_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)+(0.1200P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.3188
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C2S-S2
 1.7 with sigma of 0.02
 S2-C1
 1.7 with sigma of 0.02
 S1S-C1S
 1.7 with sigma of 0.02
 C2S-S1S
 1.7 with sigma of 0.02
 O1S-S1S
 1.5 with sigma of 0.02
 S2-O1S
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C1S) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: S1S(0.85) H2SA(0.85) H2SB(0.85) H2SC(0.85) H2SD(0.15) H2SE(0.15)
 H2SF(0.15) C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) C1(0.5) H1A(0.5) H1B(0.5)
 H1C(0.5) S2(0.15)
5.a Me refined with riding coordinates:
 C2S(H2SA,H2SB,H2SC), C2S(H2SD,H2SE,H2SF), C1S(H1SA,H1SB,H1SC), C1(H1A,H1B,H1C)
5.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C2(H2)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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 0.80215(12) 0.20025(8) 0.25375(7) 0.0782(5) Uani 1 1 d . . . . .
N8 N 0.6678(3) 0.1695(2) 0.3822(2) 0.0631(10) Uani 1 1 d . . . . .
N6 N 0.8067(3) 0.0695(2) 0.3520(2) 0.0730(11) Uani 1 1 d . . . . .
H6 H 0.861093 0.056927 0.319483 0.088 Uiso 1 1 calc R U . . .
C9 C 0.6426(4) 0.1187(3) 0.4478(3) 0.0632(11) Uani 1 1 d . . . . .
N3 N 0.6499(4) 0.0121(3) 0.5384(3) 0.0823(13) Uani 1 1 d . . . . .
C7 C 0.7501(4) 0.1409(3) 0.3384(3) 0.0641(11) Uani 1 1 d . . . . .
N1 N 0.5661(3) 0.1342(2) 0.5078(2) 0.0677(11) Uani 1 1 d . . . . .
C4 C 0.6935(4) 0.0448(3) 0.4675(3) 0.0665(12) Uani 1 1 d . . . . .
O1 O 0.8370(4) -0.0514(3) 0.4227(3) 0.1131(15) Uani 1 1 d . . . . .
C5 C 0.7818(5) 0.0136(3) 0.4169(3) 0.0798(15) Uani 1 1 d . . . . .
C11 C 0.4908(4) 0.2080(3) 0.5136(3) 0.0764(14) Uani 1 1 d . . . . .
C2 C 0.5750(4) 0.0682(3) 0.5606(3) 0.0792(15) Uani 1 1 d . . . . .
H2 H 0.532126 0.063500 0.607966 0.095 Uiso 1 1 calc R U . . .
C10 C 0.4171(5) 0.2121(4) 0.4379(4) 0.104(2) Uani 1 1 d . . . . .
H10A H 0.463488 0.219596 0.390463 0.156 Uiso 1 1 calc R U . . .
H10B H 0.365843 0.258195 0.442692 0.156 Uiso 1 1 calc R U . . .
H10C H 0.375279 0.161008 0.432817 0.156 Uiso 1 1 calc R U . . .
C12 C 0.5663(5) 0.2863(3) 0.5220(4) 0.0961(18) Uani 1 1 d . . . . .
H12A H 0.615602 0.279544 0.568081 0.144 Uiso 1 1 calc R U . . .
H12B H 0.519943 0.334701 0.530072 0.144 Uiso 1 1 calc R U . . .
H12C H 0.610229 0.293123 0.473245 0.144 Uiso 1 1 calc R U . . .
C13 C 0.4159(5) 0.2002(4) 0.5909(4) 0.108(2) Uani 1 1 d . . . . .
H13A H 0.369485 0.151325 0.586443 0.162 Uiso 1 1 calc R U . . .
H13B H 0.369027 0.248837 0.595596 0.162 Uiso 1 1 calc R U . . .
H13C H 0.462832 0.195672 0.638451 0.162 Uiso 1 1 calc R U . . .
S1S S 0.60210(18) -0.01764(13) 0.22625(15) 0.1060(8) Uani 0.85 1 d D . P A 1
O1S O 0.4927(4) -0.0545(3) 0.2478(2) 0.1181(17) Uani 1 1 d D . . . .
C2S C 0.7063(8) -0.0964(6) 0.2136(8) 0.187(4) Uani 1 1 d D . . . .
H2SA H 0.776791 -0.070810 0.199577 0.281 Uiso 0.85 1 calc R U P A 1
H2SB H 0.714431 -0.127080 0.263628 0.281 Uiso 0.85 1 calc R U P A 1
H2SC H 0.683854 -0.133728 0.170623 0.281 Uiso 0.85 1 calc R U P A 1
H2SD H 0.761413 -0.103496 0.171227 0.281 Uiso 0.15 1 calc R U P A 2
H2SE H 0.731841 -0.054771 0.251549 0.281 Uiso 0.15 1 calc R U P A 2
H2SF H 0.695555 -0.148414 0.241693 0.281 Uiso 0.15 1 calc R U P A 2
C1S C 0.5926(15) -0.0219(15) 0.1135(8) 0.145(6) Uani 0.5 1 d D U P A 1
H1SA H 0.660049 0.000713 0.090080 0.217 Uiso 0.5 1 calc R U P A 1
H1SB H 0.583695 -0.078915 0.096392 0.217 Uiso 0.5 1 calc R U P A 1
H1SC H 0.528957 0.010213 0.095596 0.217 Uiso 0.5 1 calc R U P A 1
C1 C 0.5979(16) 0.0455(11) 0.1543(12) 0.155(7) Uani 0.5 1 d D U P A 2
H1A H 0.649648 0.054873 0.110128 0.232 Uiso 0.5 1 calc R U P A 2
H1B H 0.525910 0.068831 0.140447 0.232 Uiso 0.5 1 calc R U P A 2
H1C H 0.625874 0.071857 0.202925 0.232 Uiso 0.5 1 calc R U P A 2
S2 S 0.5833(12) -0.0655(10) 0.1717(9) 0.156(7) Uani 0.15 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 S1 2.018(3) 2_655 ?
S1 C7 1.790(5) . ?
N8 C9 1.379(5) . ?
N8 C7 1.296(6) . ?
N6 H6 0.8600 . ?
N6 C7 1.345(6) . ?
N6 C5 1.419(6) . ?
C9 N1 1.361(6) . ?
C9 C4 1.367(6) . ?
N3 C4 1.374(6) . ?
N3 C2 1.316(7) . ?
N1 C11 1.485(6) . ?
N1 C2 1.368(6) . ?
C4 C5 1.426(7) . ?
O1 C5 1.234(6) . ?
C11 C10 1.517(7) . ?
C11 C12 1.547(7) . ?
C11 C13 1.551(7) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
S1S O1S 1.471(4) . ?
S1S C2S 1.778(9) . ?
S1S C1S 1.848(13) . ?
O1S S2 1.654(14) . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 0.9600 . ?
C2S H2SD 0.9600 . ?
C2S H2SE 0.9600 . ?
C2S H2SF 0.9600 . ?
C2S S2 1.688(14) . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 S2 1.808(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 S1 101.93(18) . 2_655 ?
C7 N8 C9 112.6(4) . . ?
C7 N6 H6 118.2 . . ?
C7 N6 C5 123.7(4) . . ?
C5 N6 H6 118.2 . . ?
N1 C9 N8 126.8(4) . . ?
N1 C9 C4 106.4(4) . . ?
C4 C9 N8 126.7(4) . . ?
C2 N3 C4 103.2(4) . . ?
N8 C7 S1 120.0(4) . . ?
N8 C7 N6 126.0(4) . . ?
N6 C7 S1 113.9(4) . . ?
C9 N1 C11 126.3(4) . . ?
C9 N1 C2 105.3(4) . . ?
C2 N1 C11 128.4(4) . . ?
C9 C4 N3 111.2(4) . . ?
C9 C4 C5 119.4(4) . . ?
N3 C4 C5 129.3(4) . . ?
N6 C5 C4 111.5(4) . . ?
O1 C5 N6 118.6(5) . . ?
O1 C5 C4 129.8(5) . . ?
N1 C11 C10 109.3(4) . . ?
N1 C11 C12 107.5(4) . . ?
N1 C11 C13 109.5(4) . . ?
C10 C11 C12 111.9(4) . . ?
C10 C11 C13 109.7(5) . . ?
C12 C11 C13 108.9(5) . . ?
N3 C2 N1 113.9(5) . . ?
N3 C2 H2 123.1 . . ?
N1 C2 H2 123.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1S S1S C2S 111.1(4) . . ?
O1S S1S C1S 99.8(6) . . ?
C2S S1S C1S 84.3(8) . . ?
S1S C2S H2SA 109.5 . . ?
S1S C2S H2SB 109.5 . . ?
S1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
H2SD C2S H2SE 109.5 . . ?
H2SD C2S H2SF 109.5 . . ?
H2SE C2S H2SF 109.5 . . ?
S2 C2S H2SD 109.5 . . ?
S2 C2S H2SE 109.5 . . ?
S2 C2S H2SF 109.5 . . ?
S1S C1S H1SA 109.5 . . ?
S1S C1S H1SB 109.5 . . ?
S1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S2 C1 H1A 109.5 . . ?
S2 C1 H1B 109.5 . . ?
S2 C1 H1C 109.5 . . ?
O1S S2 C2S 106.9(8) . . ?
O1S S2 C1 94.4(10) . . ?
C2S S2 C1 105.6(10) . . ?

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 S1 C7 N8 -2.6(4) 2_655 . . . ?
S1 S1 C7 N6 -180.0(3) 2_655 . . . ?
N8 C9 N1 C11 2.3(7) . . . . ?
N8 C9 N1 C2 -177.2(4) . . . . ?
N8 C9 C4 N3 177.9(4) . . . . ?
N8 C9 C4 C5 -0.5(7) . . . . ?
C9 N8 C7 S1 -176.3(3) . . . . ?
C9 N8 C7 N6 0.8(6) . . . . ?
C9 N1 C11 C10 59.0(6) . . . . ?
C9 N1 C11 C12 -62.6(6) . . . . ?
C9 N1 C11 C13 179.2(5) . . . . ?
C9 N1 C2 N3 -0.7(6) . . . . ?
C9 C4 C5 N6 2.3(6) . . . . ?
C9 C4 C5 O1 -178.7(5) . . . . ?
N3 C4 C5 N6 -175.8(5) . . . . ?
N3 C4 C5 O1 3.2(9) . . . . ?
C7 N8 C9 N1 175.3(4) . . . . ?
C7 N8 C9 C4 -1.2(6) . . . . ?
C7 N6 C5 C4 -2.8(6) . . . . ?
C7 N6 C5 O1 178.1(5) . . . . ?
N1 C9 C4 N3 0.9(5) . . . . ?
N1 C9 C4 C5 -177.6(4) . . . . ?
C4 C9 N1 C11 179.3(4) . . . . ?
C4 C9 N1 C2 -0.1(5) . . . . ?
C4 N3 C2 N1 1.2(6) . . . . ?
C5 N6 C7 S1 178.5(4) . . . . ?
C5 N6 C7 N8 1.3(7) . . . . ?
C11 N1 C2 N3 179.9(4) . . . . ?
C2 N3 C4 C9 -1.2(6) . . . . ?
C2 N3 C4 C5 177.0(5) . . . . ?
C2 N1 C11 C10 -121.6(5) . . . . ?
C2 N1 C11 C12 116.7(5) . . . . ?
C2 N1 C11 C13 -1.5(7) . . . . ?


_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 1.186
_oxdiff_exptl_absorpt_empirical_full_min 0.844
####################################################################### 
# 
# 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_exp_1044
_database_code_depnum_ccdc_archive 'CCDC 2163813'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2022-04-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 N8 O2 S2, 2(C2 H6 O S)'
_chemical_formula_sum            'C22 H34 N8 O4 S4'
_chemical_formula_weight         602.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.4433(9)
_cell_length_b                   27.1914(16)
_cell_length_c                   16.9657(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.129(7)
_cell_angle_gamma                90
_cell_volume                     6039.6(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3254
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0590
_cell_measurement_theta_min      3.7940
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23879
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.496
_diffrn_reflns_theta_min         3.749
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  44.00   1.00   60.00    --  -23.92  57.00  90.00   89
  2  ω    -91.00  -3.00   1.00   60.00    --  -23.92 -77.00 120.00   88
  3  ω    -90.00   3.00   1.00   60.00    --  -23.92 -77.00-150.00   93
  4  ω    -51.00  40.00   1.00   60.00    --  -23.92  77.00 -30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162991000
_diffrn_orient_matrix_UB_12      0.0224696000
_diffrn_orient_matrix_UB_13      0.0141634000
_diffrn_orient_matrix_UB_21      -0.0516246000
_diffrn_orient_matrix_UB_22      -0.0065799000
_diffrn_orient_matrix_UB_23      -0.0163842000
_diffrn_orient_matrix_UB_31      -0.0022469000
_diffrn_orient_matrix_UB_32      -0.0114771000
_diffrn_orient_matrix_UB_33      0.0370977000
_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                3428
_reflns_number_total             8489
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         8489
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.0683
_refine_ls_restrained_S_all      1.022
_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)+(0.1007P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.2487
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C3-C12
 1.54 with sigma of 0.02
 C12-C13
 1.54 with sigma of 0.02
 C12-C11
 1.54 with sigma of 0.02
 C14-C00W
 1.54 with sigma of 0.02
 C14-C5
 1.54 with sigma of 0.02
 C14-C7
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C2S) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S3) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: S1S(0.8) H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) H1SD(0.2)
 H1SE(0.2) H1SF(0.2) H1SA(0.8) H1SB(0.8) H1SC(0.8) C13(0.8) H13A(0.8) H13B(0.8)
 H13C(0.8) H12A(0.8) H12B(0.8) H12C(0.2) H12D(0.2) C2S(0.8) H2SA(0.8) H2SB(0.8)
 H2SC(0.8) C3(0.2) H3A(0.2) H3B(0.2) H3C(0.2) C7(0.5) H7A(0.5) H7B(0.5)
 H7C(0.5) C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5) C1(0.2) H1A(0.2) H1B(0.2) H1C(0.2)
 S3(0.2)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C00S(H00A,H00B), C11(H11A,H11B), C00W(H00C,H00D), C14(H14A,
 H14B), C14(H14C,H14D), C12(H12A,H12B), C12(H12C,H12D)
5.b Me refined with riding coordinates:
 C4S(H4SA,H4SB,H4SC), C13(H13A,H13B,H13C), C3(H3A,H3B,H3C), C7(H7A,H7B,H7C),
 C5(H5A,H5B,H5C)
5.c Aromatic/amide H refined with riding coordinates:
 N16(H16), N3(H3), C6(H6), C19(H19)
5.d Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C1S(H1SD,H1SE,H1SF), C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,
 H2SC), C1(H1A,H1B,H1C)
;
_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 0.77604(7) 0.70842(4) 0.86245(6) 0.0715(3) Uani 1 1 d . . . . .
S2 S 0.77577(7) 0.63467(4) 0.85230(6) 0.0744(3) Uani 1 1 d . . . . .
S2S S 0.76958(9) 0.88200(4) 0.90065(8) 0.0932(4) Uani 1 1 d . . . . .
S1S S 0.78609(12) 0.47644(6) 0.88789(11) 0.0878(4) Uani 0.8 1 d . . P A 1
N1 N 0.6243(2) 0.69248(10) 0.73151(17) 0.0626(7) Uani 1 1 d . . . . .
O2S O 0.7962(2) 0.83025(9) 0.88522(19) 0.0912(9) Uani 1 1 d . . . . .
N14 N 0.8630(2) 0.66225(10) 0.73166(18) 0.0645(7) Uani 1 1 d . . . . .
N16 N 0.8341(2) 0.57779(10) 0.74612(18) 0.0663(7) Uani 1 1 d . . . . .
H16 H 0.810937 0.556393 0.774714 0.080 Uiso 1 1 calc R U . . .
N3 N 0.6733(2) 0.77427(10) 0.76234(18) 0.0643(7) Uani 1 1 d . . . . .
H3 H 0.712327 0.792998 0.796957 0.077 Uiso 1 1 calc R U . . .
N7 N 0.4941(2) 0.68740(11) 0.60800(18) 0.0673(8) Uani 1 1 d . . . . .
O1 O 0.6094(2) 0.84173(10) 0.6863(2) 0.0979(9) Uani 1 1 d . . . . .
O2 O 0.8694(3) 0.51626(10) 0.66493(19) 0.1040(10) Uani 1 1 d . . . . .
N5 N 0.4753(2) 0.76678(12) 0.57366(19) 0.0729(8) Uani 1 1 d . . . . .
N20 N 0.9311(2) 0.67707(11) 0.61385(19) 0.0738(8) Uani 1 1 d . . . . .
N18 N 0.9414(3) 0.60035(14) 0.5692(2) 0.0854(9) Uani 1 1 d . . . . .
C21 C 0.8969(2) 0.64727(13) 0.6659(2) 0.0621(8) Uani 1 1 d . . . . .
C2 C 0.6797(2) 0.72576(12) 0.7764(2) 0.0593(8) Uani 1 1 d . . . . .
O1S O 0.7420(2) 0.51229(12) 0.8255(2) 0.1134(11) Uani 1 1 d . . . . .
C8 C 0.5602(2) 0.71296(13) 0.6664(2) 0.0607(8) Uani 1 1 d . . . . .
C15 C 0.8321(2) 0.62523(13) 0.7681(2) 0.0619(8) Uani 1 1 d . . . . .
C22 C 0.9033(3) 0.60016(14) 0.6377(2) 0.0672(9) Uani 1 1 d . . . . .
C9 C 0.5477(3) 0.76121(13) 0.6447(2) 0.0626(8) Uani 1 1 d . . . . .
C4 C 0.6076(3) 0.79743(14) 0.6952(2) 0.0685(9) Uani 1 1 d . . . . .
C17 C 0.8713(3) 0.56029(14) 0.6798(2) 0.0733(10) Uani 1 1 d . . . . .
C6 C 0.4450(3) 0.72189(16) 0.5538(2) 0.0748(10) Uani 1 1 d . . . . .
H6 H 0.395281 0.714100 0.507767 0.090 Uiso 1 1 calc R U . . .
C19 C 0.9556(3) 0.64707(18) 0.5575(3) 0.0865(12) Uani 1 1 d . . . . .
H19 H 0.980512 0.658724 0.514206 0.104 Uiso 1 1 calc R U . . .
C10 C 0.4775(3) 0.63480(15) 0.6064(3) 0.0853(12) Uani 1 1 d . . . . .
H10A H 0.416785 0.627307 0.564972 0.102 Uiso 1 1 calc R U . . .
H10B H 0.464997 0.624621 0.658031 0.102 Uiso 1 1 calc R U . . .
C00S C 0.9451(4) 0.73067(16) 0.6213(3) 0.0945(14) Uani 1 1 d . . . . .
H00A H 0.981542 0.738422 0.676084 0.113 Uiso 1 1 calc R U . . .
H00B H 0.986944 0.741413 0.584909 0.113 Uiso 1 1 calc R U . . .
C4S C 0.6357(4) 0.88655(19) 0.8786(4) 0.1224(18) Uani 1 1 d . . . . .
H4SA H 0.616409 0.919639 0.888101 0.184 Uiso 1 1 calc R U . . .
H4SB H 0.608646 0.878061 0.822972 0.184 Uiso 1 1 calc R U . . .
H4SC H 0.608989 0.864440 0.912820 0.184 Uiso 1 1 calc R U . . .
C11 C 0.5639(5) 0.6060(2) 0.5902(4) 0.136(2) Uani 1 1 d D . . . .
H11A H 0.624376 0.613754 0.631655 0.164 Uiso 1 1 calc R U . . .
H11B H 0.576477 0.616633 0.538711 0.164 Uiso 1 1 calc R U . . .
C3S C 0.7896(5) 0.91546(18) 0.8168(4) 0.137(2) Uani 1 1 d . . . . .
H3SA H 0.860624 0.914179 0.815653 0.205 Uiso 1 1 calc R U . . .
H3SB H 0.769614 0.949068 0.821162 0.205 Uiso 1 1 calc R U . . .
H3SC H 0.749521 0.901401 0.767936 0.205 Uiso 1 1 calc R U . . .
C00W C 0.8505(5) 0.7574(2) 0.6032(5) 0.151(2) Uani 1 1 d D . . . .
H00C H 0.811656 0.748586 0.642809 0.181 Uiso 1 1 calc R U . . .
H00D H 0.811420 0.746951 0.550589 0.181 Uiso 1 1 calc R U . . .
C14 C 0.8609(9) 0.8119(3) 0.6026(7) 0.219(5) Uani 1 1 d D . . . .
H14A H 0.889475 0.819392 0.556392 0.262 Uiso 0.5 1 calc R U P B 1
H14B H 0.791695 0.824616 0.589730 0.262 Uiso 0.5 1 calc R U P B 1
H14C H 0.886186 0.819726 0.659371 0.262 Uiso 0.5 1 calc R U P C 2
H14D H 0.918708 0.816737 0.578120 0.262 Uiso 0.5 1 calc R U P C 2
C1S C 0.9105(4) 0.4629(2) 0.8815(4) 0.132(2) Uani 1 1 d . . . . .
H1SD H 0.874077 0.449161 0.831078 0.199 Uiso 0.2 1 calc R U P A 2
H1SE H 0.938526 0.436797 0.917992 0.199 Uiso 0.2 1 calc R U P A 2
H1SF H 0.964831 0.483418 0.872297 0.199 Uiso 0.2 1 calc R U P A 2
H1SA H 0.911019 0.432744 0.852165 0.199 Uiso 0.8 1 calc R U P A 1
H1SB H 0.952772 0.459364 0.935044 0.199 Uiso 0.8 1 calc R U P A 1
H1SC H 0.936399 0.489060 0.853909 0.199 Uiso 0.8 1 calc R U P A 1
C13 C 0.5157(10) 0.5257(4) 0.6492(10) 0.270(8) Uani 0.8 1 d D . P D 1
H13A H 0.511349 0.491174 0.637309 0.405 Uiso 0.8 1 calc R U P D 1
H13B H 0.563067 0.531047 0.700112 0.405 Uiso 0.8 1 calc R U P D 1
H13C H 0.449590 0.537815 0.652252 0.405 Uiso 0.8 1 calc R U P D 1
C12 C 0.5497(8) 0.5509(3) 0.5876(7) 0.210(4) Uani 1 1 d D . . . .
H12A H 0.502068 0.543249 0.536966 0.252 Uiso 0.8 1 calc R U P D 1
H12B H 0.614762 0.536528 0.584496 0.252 Uiso 0.8 1 calc R U P D 1
H12C H 0.482605 0.542138 0.555753 0.252 Uiso 0.2 1 calc R U P D 2
H12D H 0.557593 0.537649 0.641721 0.252 Uiso 0.2 1 calc R U P D 2
C2S C 0.8221(8) 0.5145(3) 0.9747(5) 0.150(4) Uani 0.8 1 d . U P A 1
H2SA H 0.873201 0.537423 0.966908 0.226 Uiso 0.8 1 calc R U P A 1
H2SB H 0.849079 0.494429 1.021248 0.226 Uiso 0.8 1 calc R U P A 1
H2SC H 0.763366 0.532070 0.982932 0.226 Uiso 0.8 1 calc R U P A 1
C3 C 0.634(3) 0.531(2) 0.548(3) 0.28(3) Uani 0.2 1 d D U P D 2
H3A H 0.629780 0.496209 0.543948 0.422 Uiso 0.2 1 calc R U P D 2
H3B H 0.625208 0.545157 0.494431 0.422 Uiso 0.2 1 calc R U P D 2
H3C H 0.699700 0.540698 0.579830 0.422 Uiso 0.2 1 calc R U P D 2
C7 C 0.9143(15) 0.8409(7) 0.6656(12) 0.216(9) Uani 0.5 1 d D U P E 1
H7A H 0.908853 0.874773 0.649484 0.325 Uiso 0.5 1 calc R U P E 1
H7B H 0.886034 0.836555 0.712281 0.325 Uiso 0.5 1 calc R U P E 1
H7C H 0.984863 0.831276 0.678586 0.325 Uiso 0.5 1 calc R U P E 1
C5 C 0.7996(16) 0.8507(8) 0.5745(15) 0.260(10) Uani 0.5 1 d D U P E 2
H5A H 0.837506 0.880677 0.587113 0.390 Uiso 0.5 1 calc R U P E 2
H5B H 0.775491 0.847886 0.516908 0.390 Uiso 0.5 1 calc R U P E 2
H5C H 0.742387 0.850930 0.599616 0.390 Uiso 0.5 1 calc R U P E 2
C1 C 0.7413(18) 0.4550(10) 0.9459(18) 0.132(9) Uani 0.2 1 d . U P A 2
H1A H 0.730074 0.433332 0.900035 0.198 Uiso 0.2 1 calc R U P A 2
H1B H 0.676803 0.466992 0.953200 0.198 Uiso 0.2 1 calc R U P A 2
H1C H 0.775320 0.437394 0.993482 0.198 Uiso 0.2 1 calc R U P A 2
S3 S 0.8148(8) 0.5031(3) 0.9300(6) 0.112(3) Uani 0.2 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 S2 2.0129(15) . ?
S1 C2 1.781(4) . ?
S2 C15 1.781(3) . ?
S2S O2S 1.490(3) . ?
S2S C4S 1.757(5) . ?
S2S C3S 1.760(6) . ?
S1S O1S 1.462(3) . ?
S1S C1S 1.740(5) . ?
S1S C2S 1.774(9) . ?
N1 C2 1.303(4) . ?
N1 C8 1.357(4) . ?
N14 C21 1.360(4) . ?
N14 C15 1.298(4) . ?
N16 H16 0.8600 . ?
N16 C15 1.345(4) . ?
N16 C17 1.414(5) . ?
N3 H3 0.8600 . ?
N3 C2 1.340(4) . ?
N3 C4 1.420(4) . ?
N7 C8 1.361(4) . ?
N7 C6 1.373(5) . ?
N7 C10 1.447(5) . ?
O1 C4 1.215(4) . ?
O2 C17 1.223(4) . ?
N5 C9 1.375(5) . ?
N5 C6 1.306(5) . ?
N20 C21 1.354(4) . ?
N20 C19 1.352(5) . ?
N20 C00S 1.471(5) . ?
N18 C22 1.373(5) . ?
N18 C19 1.307(5) . ?
C21 C22 1.376(5) . ?
O1S S3 1.838(10) . ?
C8 C9 1.363(5) . ?
C22 C17 1.417(5) . ?
C9 C4 1.429(5) . ?
C6 H6 0.9300 . ?
C19 H19 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.476(6) . ?
C00S H00A 0.9700 . ?
C00S H00B 0.9700 . ?
C00S C00W 1.436(7) . ?
C4S H4SA 0.9600 . ?
C4S H4SB 0.9600 . ?
C4S H4SC 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.510(8) . ?
C3S H3SA 0.9600 . ?
C3S H3SB 0.9600 . ?
C3S H3SC 0.9600 . ?
C00W H00C 0.9700 . ?
C00W H00D 0.9700 . ?
C00W C14 1.487(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C7 1.390(14) . ?
C14 C5 1.357(15) . ?
C1S H1SD 0.9600 . ?
C1S H1SE 0.9600 . ?
C1S H1SF 0.9600 . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C1S S3 2.002(11) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C12 1.410(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C12 C3 1.540(19) . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 S3 1.70(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 S2 101.94(12) . . ?
C15 S2 S1 102.67(12) . . ?
O2S S2S C4S 107.7(2) . . ?
O2S S2S C3S 105.0(2) . . ?
C4S S2S C3S 97.4(3) . . ?
O1S S1S C1S 109.5(2) . . ?
O1S S1S C2S 101.6(3) . . ?
C1S S1S C2S 95.2(4) . . ?
C2 N1 C8 111.4(3) . . ?
C15 N14 C21 111.2(3) . . ?
C15 N16 H16 117.4 . . ?
C15 N16 C17 125.2(3) . . ?
C17 N16 H16 117.4 . . ?
C2 N3 H3 117.2 . . ?
C2 N3 C4 125.7(3) . . ?
C4 N3 H3 117.2 . . ?
C8 N7 C6 105.9(3) . . ?
C8 N7 C10 126.2(3) . . ?
C6 N7 C10 127.9(3) . . ?
C6 N5 C9 103.9(3) . . ?
C21 N20 C00S 126.3(3) . . ?
C19 N20 C21 105.8(3) . . ?
C19 N20 C00S 127.7(3) . . ?
C19 N18 C22 103.1(3) . . ?
N14 C21 C22 128.5(3) . . ?
N20 C21 N14 125.6(3) . . ?
N20 C21 C22 105.9(3) . . ?
N1 C2 S1 120.5(3) . . ?
N1 C2 N3 125.1(3) . . ?
N3 C2 S1 114.4(3) . . ?
N1 C8 N7 124.9(3) . . ?
N1 C8 C9 129.2(3) . . ?
N7 C8 C9 106.0(3) . . ?
N14 C15 S2 120.7(3) . . ?
N14 C15 N16 125.7(3) . . ?
N16 C15 S2 113.5(2) . . ?
N18 C22 C21 110.8(3) . . ?
N18 C22 C17 130.0(4) . . ?
C21 C22 C17 119.2(3) . . ?
N5 C9 C4 129.9(3) . . ?
C8 C9 N5 111.2(3) . . ?
C8 C9 C4 118.9(3) . . ?
N3 C4 C9 109.8(3) . . ?
O1 C4 N3 120.9(3) . . ?
O1 C4 C9 129.2(4) . . ?
N16 C17 C22 110.2(3) . . ?
O2 C17 N16 119.9(4) . . ?
O2 C17 C22 129.8(4) . . ?
N7 C6 H6 123.5 . . ?
N5 C6 N7 113.0(4) . . ?
N5 C6 H6 123.5 . . ?
N20 C19 H19 122.8 . . ?
N18 C19 N20 114.4(3) . . ?
N18 C19 H19 122.8 . . ?
N7 C10 H10A 108.8 . . ?
N7 C10 H10B 108.8 . . ?
N7 C10 C11 113.8(4) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
N20 C00S H00A 108.9 . . ?
N20 C00S H00B 108.9 . . ?
H00A C00S H00B 107.8 . . ?
C00W C00S N20 113.2(4) . . ?
C00W C00S H00A 108.9 . . ?
C00W C00S H00B 108.9 . . ?
S2S C4S H4SA 109.5 . . ?
S2S C4S H4SB 109.5 . . ?
S2S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C12 115.6(5) . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
S2S C3S H3SA 109.5 . . ?
S2S C3S H3SB 109.5 . . ?
S2S C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
C00S C00W H00C 108.5 . . ?
C00S C00W H00D 108.5 . . ?
C00S C00W C14 115.2(6) . . ?
H00C C00W H00D 107.5 . . ?
C14 C00W H00C 108.5 . . ?
C14 C00W H00D 108.5 . . ?
C00W C14 H14A 105.7 . . ?
C00W C14 H14B 105.7 . . ?
C00W C14 H14C 103.0 . . ?
C00W C14 H14D 103.0 . . ?
H14A C14 H14B 106.2 . . ?
H14C C14 H14D 105.1 . . ?
C7 C14 C00W 126.3(13) . . ?
C7 C14 H14A 105.7 . . ?
C7 C14 H14B 105.7 . . ?
C5 C14 C00W 136.6(16) . . ?
C5 C14 H14C 103.0 . . ?
C5 C14 H14D 103.0 . . ?
S1S C1S H1SA 109.5 . . ?
S1S C1S H1SB 109.5 . . ?
S1S C1S H1SC 109.5 . . ?
H1SD C1S H1SE 109.5 . . ?
H1SD C1S H1SF 109.5 . . ?
H1SE C1S H1SF 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
S3 C1S H1SD 109.5 . . ?
S3 C1S H1SE 109.5 . . ?
S3 C1S H1SF 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
C11 C12 H12A 107.0 . . ?
C11 C12 H12B 107.0 . . ?
C11 C12 H12C 110.8 . . ?
C11 C12 H12D 110.8 . . ?
C11 C12 C3 105(2) . . ?
C13 C12 C11 121.3(9) . . ?
C13 C12 H12A 107.0 . . ?
C13 C12 H12B 107.0 . . ?
H12A C12 H12B 106.7 . . ?
H12C C12 H12D 108.9 . . ?
C3 C12 H12C 110.8 . . ?
C3 C12 H12D 110.8 . . ?
S1S C2S H2SA 109.5 . . ?
S1S C2S H2SB 109.5 . . ?
S1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C12 C3 H3A 109.5 . . ?
C12 C3 H3B 109.5 . . ?
C12 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C14 C7 H7A 109.5 . . ?
C14 C7 H7B 109.5 . . ?
C14 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C5 H5A 109.5 . . ?
C14 C5 H5B 109.5 . . ?
C14 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S3 C1 H1A 109.5 . . ?
S3 C1 H1B 109.5 . . ?
S3 C1 H1C 109.5 . . ?
O1S S3 C1S 85.9(4) . . ?
C1 S3 O1S 93.2(10) . . ?
C1 S3 C1S 95.5(12) . . ?

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 S2 C15 N14 1.4(3) . . . . ?
S1 S2 C15 N16 -175.9(2) . . . . ?
S2 S1 C2 N1 6.5(3) . . . . ?
S2 S1 C2 N3 -171.5(2) . . . . ?
N1 C8 C9 N5 179.4(3) . . . . ?
N1 C8 C9 C4 -0.5(5) . . . . ?
N14 C21 C22 N18 179.8(3) . . . . ?
N14 C21 C22 C17 0.3(6) . . . . ?
N7 C8 C9 N5 -0.2(4) . . . . ?
N7 C8 C9 C4 179.9(3) . . . . ?
N7 C10 C11 C12 -179.8(6) . . . . ?
N5 C9 C4 N3 -179.5(3) . . . . ?
N5 C9 C4 O1 -1.2(6) . . . . ?
N20 C21 C22 N18 0.2(4) . . . . ?
N20 C21 C22 C17 -179.3(3) . . . . ?
N20 C00S C00W C14 -174.7(6) . . . . ?
N18 C22 C17 N16 -178.0(4) . . . . ?
N18 C22 C17 O2 -0.4(7) . . . . ?
C21 N14 C15 S2 -175.8(2) . . . . ?
C21 N14 C15 N16 1.2(5) . . . . ?
C21 N20 C19 N18 -0.8(5) . . . . ?
C21 N20 C00S C00W -73.8(6) . . . . ?
C21 C22 C17 N16 1.5(5) . . . . ?
C21 C22 C17 O2 179.1(4) . . . . ?
C2 N1 C8 N7 179.0(3) . . . . ?
C2 N1 C8 C9 -0.6(5) . . . . ?
C2 N3 C4 O1 -177.7(3) . . . . ?
C2 N3 C4 C9 0.7(4) . . . . ?
C8 N1 C2 S1 -176.1(2) . . . . ?
C8 N1 C2 N3 1.8(4) . . . . ?
C8 N7 C6 N5 0.1(4) . . . . ?
C8 N7 C10 C11 -70.8(5) . . . . ?
C8 C9 C4 N3 0.4(4) . . . . ?
C8 C9 C4 O1 178.7(4) . . . . ?
C15 N14 C21 N20 177.9(3) . . . . ?
C15 N14 C21 C22 -1.7(5) . . . . ?
C15 N16 C17 O2 -179.8(3) . . . . ?
C15 N16 C17 C22 -1.9(5) . . . . ?
C22 N18 C19 N20 0.9(5) . . . . ?
C9 N5 C6 N7 -0.3(4) . . . . ?
C4 N3 C2 S1 175.9(2) . . . . ?
C4 N3 C2 N1 -2.0(5) . . . . ?
C17 N16 C15 S2 177.8(3) . . . . ?
C17 N16 C15 N14 0.6(5) . . . . ?
C6 N7 C8 N1 -179.6(3) . . . . ?
C6 N7 C8 C9 0.0(3) . . . . ?
C6 N7 C10 C11 111.8(5) . . . . ?
C6 N5 C9 C8 0.3(4) . . . . ?
C6 N5 C9 C4 -179.9(3) . . . . ?
C19 N20 C21 N14 -179.3(4) . . . . ?
C19 N20 C21 C22 0.3(4) . . . . ?
C19 N20 C00S C00W 110.9(5) . . . . ?
C19 N18 C22 C21 -0.6(4) . . . . ?
C19 N18 C22 C17 178.8(4) . . . . ?
C10 N7 C8 N1 2.6(5) . . . . ?
C10 N7 C8 C9 -177.8(3) . . . . ?
C10 N7 C6 N5 177.9(3) . . . . ?
C10 C11 C12 C13 -48.9(13) . . . . ?
C10 C11 C12 C3 165(2) . . . . ?
C00S N20 C21 N14 4.6(6) . . . . ?
C00S N20 C21 C22 -175.8(4) . . . . ?
C00S N20 C19 N18 175.3(4) . . . . ?
C00S C00W C14 C7 -56.1(17) . . . . ?
C00S C00W C14 C5 163.8(18) . . . . ?


_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 1.092
_oxdiff_exptl_absorpt_empirical_full_min 0.926
