# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_388
_database_code_depnum_ccdc_archive 'CCDC 2288489'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2023-07-17
_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         'C19 H21 N3 O2 S'
_chemical_formula_sum            'C19 H21 N3 O2 S'
_chemical_formula_weight         355.45
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.247(3)
_cell_length_b                   9.0994(10)
_cell_length_c                   15.279(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.13(3)
_cell_angle_gamma                90
_cell_volume                     1762.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1699
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.2300
_cell_measurement_theta_min      3.9700
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_unetI/netI     0.1190
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8708
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         3.633
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00  85.00   1.00   10.00    --   17.64  66.00  -0.00   74
  2  ω    -29.00  -4.00   1.00   10.00    --   17.64 -66.00-134.00   25
  3  ω    -11.00  23.00   1.00   10.00    --   17.64  77.00 -30.00   34
  4  ω    -37.00  45.00   1.00   10.00    --   17.64 -77.00-150.00   82
  5  ω    -11.00  39.00   1.00   10.00    --   17.64  77.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1921
_reflns_number_total             3808
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.542
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1480
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.055
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1776
_refine_ls_wR_factor_ref         0.2509
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_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
C1 C 0.7529(3) 0.1485(5) 0.4609(3) 0.0518(11) Uani 1 1 d . . . . .
C2 C 0.5178(3) 0.4270(4) 0.2347(3) 0.0481(10) Uani 1 1 d . . . . .
C3 C 0.6039(3) 0.4869(4) 0.3327(3) 0.0408(9) Uani 1 1 d . . . . .
C4 C 0.5913(4) 0.7379(4) 0.4120(3) 0.0510(10) Uani 1 1 d . . . . .
H4 H 0.662329 0.741299 0.457325 0.061 Uiso 1 1 calc R U . . .
C5 C 0.5237(4) 0.8479(4) 0.4083(4) 0.0570(12) Uani 1 1 d . . . . .
H5 H 0.549194 0.928434 0.450092 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4181(4) 0.8393(4) 0.3427(4) 0.0613(13) Uani 1 1 d . . . . .
H6 H 0.373346 0.912135 0.344863 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3746(4) 0.7278(4) 0.2735(3) 0.0513(11) Uani 1 1 d . . . . .
C8 C 0.4458(3) 0.6209(4) 0.2769(3) 0.0435(10) Uani 1 1 d . . . . .
C9 C 0.5516(3) 0.6221(4) 0.3469(3) 0.0406(9) Uani 1 1 d . . . . .
C10 C 0.2606(4) 0.7237(5) 0.2003(4) 0.0710(14) Uani 1 1 d . . . . .
H10A H 0.223466 0.658681 0.223275 0.107 Uiso 1 1 calc R U . . .
H10B H 0.253728 0.689031 0.138315 0.107 Uiso 1 1 calc R U . . .
H10C H 0.231267 0.820676 0.192273 0.107 Uiso 1 1 calc R U . . .
C11 C 0.5431(3) 0.2707(4) 0.4002(4) 0.0570(12) Uani 1 1 d . . . . .
H11A H 0.486015 0.330417 0.396954 0.086 Uiso 1 1 calc R U . . .
H11B H 0.563698 0.202451 0.453720 0.086 Uiso 1 1 calc R U . . .
H11C H 0.520707 0.217659 0.339669 0.086 Uiso 1 1 calc R U . . .
C12 C 0.6358(3) 0.3679(4) 0.4164(3) 0.0422(9) Uani 1 1 d . . . . .
C13 C 0.6767(4) 0.4383(4) 0.5174(3) 0.0543(11) Uani 1 1 d . . . . .
H13A H 0.727926 0.512162 0.524850 0.082 Uiso 1 1 calc R U . . .
H13B H 0.708870 0.364553 0.567241 0.082 Uiso 1 1 calc R U . . .
H13C H 0.619096 0.482706 0.524001 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7277(3) 0.2866(4) 0.4128(3) 0.0437(9) Uani 1 1 d . . . . .
C15 C 0.7839(3) 0.3634(4) 0.3767(3) 0.0437(9) Uani 1 1 d . . . . .
C16 C 0.9157(3) 0.4083(5) 0.3169(4) 0.0578(12) Uani 1 1 d . . . . .
H16A H 0.877195 0.499002 0.291088 0.069 Uiso 1 1 calc R U . . .
H16B H 0.901353 0.343209 0.261932 0.069 Uiso 1 1 calc R U . . .
C17 C 1.0325(4) 0.4405(5) 0.3707(4) 0.0673(14) Uani 1 1 d . . . . .
H17A H 1.055372 0.481823 0.325049 0.081 Uiso 1 1 calc R U . . .
H17B H 1.045812 0.512662 0.421739 0.081 Uiso 1 1 calc R U . . .
C18 C 1.0604(4) 0.2528(5) 0.4818(4) 0.0639(13) Uani 1 1 d . . . . .
H18A H 1.075750 0.323979 0.533839 0.077 Uiso 1 1 calc R U . . .
H18B H 1.101681 0.165265 0.511350 0.077 Uiso 1 1 calc R U . . .
C19 C 0.9447(3) 0.2139(4) 0.4362(4) 0.0577(12) Uani 1 1 d . . . . .
H19A H 0.930779 0.132127 0.391228 0.069 Uiso 1 1 calc R U . . .
H19B H 0.926243 0.183758 0.487290 0.069 Uiso 1 1 calc R U . . .
N1 N 0.4275(3) 0.5020(4) 0.2135(3) 0.0475(9) Uani 1 1 d . . . . .
N2 N 0.7637(3) 0.0395(4) 0.5012(3) 0.0667(12) Uani 1 1 d . . . . .
N3 N 0.8800(3) 0.3394(4) 0.3832(3) 0.0497(9) Uani 1 1 d . . . . .
O1 O 0.5274(3) 0.3288(3) 0.1850(2) 0.0663(9) Uani 1 1 d . . . . .
O2 O 1.0915(3) 0.3111(3) 0.4137(3) 0.0721(10) Uani 1 1 d . . . . .
H1 H 0.376(3) 0.491(3) 0.159(3) 0.022(9) Uiso 1 1 d . . . . .
S1 S 0.72241(9) 0.53026(11) 0.32242(9) 0.0509(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.417(5) . ?
C1 N2 1.140(5) . ?
C2 C3 1.539(6) . ?
C2 N1 1.359(5) . ?
C2 O1 1.219(4) . ?
C3 C9 1.505(5) . ?
C3 C12 1.576(5) . ?
C3 S1 1.809(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(6) . ?
C4 C9 1.381(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(6) . ?
C7 C8 1.390(5) . ?
C7 C10 1.495(6) . ?
C8 C9 1.394(5) . ?
C8 N1 1.395(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 C12 1.514(5) . ?
C12 C13 1.520(6) . ?
C12 C14 1.527(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.354(5) . ?
C15 N3 1.345(5) . ?
C15 S1 1.760(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.511(6) . ?
C16 N3 1.465(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 O2 1.422(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.511(6) . ?
C18 O2 1.408(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 N3 1.459(5) . ?
N1 H1 0.83(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C14 172.6(5) . . ?
N1 C2 C3 107.6(3) . . ?
O1 C2 C3 126.8(4) . . ?
O1 C2 N1 125.6(4) . . ?
C2 C3 C12 110.7(3) . . ?
C2 C3 S1 110.7(3) . . ?
C9 C3 C2 101.7(3) . . ?
C9 C3 C12 115.0(3) . . ?
C9 C3 S1 112.2(2) . . ?
C12 C3 S1 106.6(2) . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C9 118.5(4) . . ?
C9 C4 H4 120.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 118.2 . . ?
C5 C6 C7 123.6(4) . . ?
C7 C6 H6 118.2 . . ?
C6 C7 C10 122.8(4) . . ?
C8 C7 C6 114.7(4) . . ?
C8 C7 C10 122.4(4) . . ?
C7 C8 C9 122.5(4) . . ?
C7 C8 N1 127.9(4) . . ?
C9 C8 N1 109.5(3) . . ?
C4 C9 C3 131.3(4) . . ?
C4 C9 C8 120.3(4) . . ?
C8 C9 C3 108.4(3) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
C11 C12 C3 111.2(3) . . ?
C11 C12 C13 108.3(3) . . ?
C11 C12 C14 114.2(3) . . ?
C13 C12 C3 111.7(3) . . ?
C13 C12 C14 107.7(3) . . ?
C14 C12 C3 103.8(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 C12 115.4(3) . . ?
C15 C14 C1 127.8(4) . . ?
C15 C14 C12 116.1(3) . . ?
C14 C15 S1 112.2(3) . . ?
N3 C15 C14 131.1(4) . . ?
N3 C15 S1 116.5(3) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 C17 110.5(4) . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O2 C17 C16 111.3(4) . . ?
O2 C17 H17A 109.4 . . ?
O2 C17 H17B 109.4 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
O2 C18 H18A 109.0 . . ?
O2 C18 H18B 109.0 . . ?
O2 C18 C19 113.1(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
N3 C19 C18 110.7(3) . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
C2 N1 C8 111.5(3) . . ?
C2 N1 H1 118(2) . . ?
C8 N1 H1 127(2) . . ?
C15 N3 C16 122.9(4) . . ?
C15 N3 C19 122.2(3) . . ?
C19 N3 C16 112.8(3) . . ?
C18 O2 C17 109.6(3) . . ?
C15 S1 C3 93.11(17) . . ?

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
C1 C14 C15 N3 -6.5(8) . . . . ?
C1 C14 C15 S1 179.9(3) . . . . ?
C2 C3 C9 C4 -168.4(4) . . . . ?
C2 C3 C9 C8 9.6(4) . . . . ?
C2 C3 C12 C11 -31.6(4) . . . . ?
C2 C3 C12 C13 -152.7(3) . . . . ?
C2 C3 C12 C14 91.5(4) . . . . ?
C2 C3 S1 C15 -98.5(3) . . . . ?
C3 C2 N1 C8 9.6(5) . . . . ?
C3 C12 C14 C1 -163.0(3) . . . . ?
C3 C12 C14 C15 26.0(5) . . . . ?
C4 C5 C6 C7 -4.2(7) . . . . ?
C5 C4 C9 C3 -179.7(4) . . . . ?
C5 C4 C9 C8 2.4(6) . . . . ?
C5 C6 C7 C8 1.8(6) . . . . ?
C5 C6 C7 C10 -177.4(4) . . . . ?
C6 C7 C8 C9 2.7(6) . . . . ?
C6 C7 C8 N1 -175.5(4) . . . . ?
C7 C8 C9 C3 176.8(3) . . . . ?
C7 C8 C9 C4 -4.9(6) . . . . ?
C7 C8 N1 C2 175.1(4) . . . . ?
C9 C3 C12 C11 82.9(4) . . . . ?
C9 C3 C12 C13 -38.2(4) . . . . ?
C9 C3 C12 C14 -153.9(3) . . . . ?
C9 C3 S1 C15 148.7(3) . . . . ?
C9 C4 C5 C6 1.9(6) . . . . ?
C9 C8 N1 C2 -3.3(5) . . . . ?
C10 C7 C8 C9 -178.0(4) . . . . ?
C10 C7 C8 N1 3.7(7) . . . . ?
C11 C12 C14 C1 -41.9(5) . . . . ?
C11 C12 C14 C15 147.1(4) . . . . ?
C12 C3 C9 C4 71.9(5) . . . . ?
C12 C3 C9 C8 -110.1(4) . . . . ?
C12 C3 S1 C15 21.9(3) . . . . ?
C12 C14 C15 N3 163.2(4) . . . . ?
C12 C14 C15 S1 -10.4(5) . . . . ?
C13 C12 C14 C1 78.4(4) . . . . ?
C13 C12 C14 C15 -92.6(4) . . . . ?
C14 C15 N3 C16 161.7(4) . . . . ?
C14 C15 N3 C19 -0.4(7) . . . . ?
C14 C15 S1 C3 -7.7(3) . . . . ?
C16 C17 O2 C18 -60.5(5) . . . . ?
C17 C16 N3 C15 145.7(4) . . . . ?
C17 C16 N3 C19 -50.7(5) . . . . ?
C18 C19 N3 C15 -147.5(4) . . . . ?
C18 C19 N3 C16 48.8(5) . . . . ?
C19 C18 O2 C17 59.4(5) . . . . ?
N1 C2 C3 C9 -11.5(4) . . . . ?
N1 C2 C3 C12 111.2(3) . . . . ?
N1 C2 C3 S1 -130.9(3) . . . . ?
N1 C8 C9 C3 -4.7(4) . . . . ?
N1 C8 C9 C4 173.6(3) . . . . ?
N3 C15 S1 C3 177.7(3) . . . . ?
N3 C16 C17 O2 56.4(5) . . . . ?
O1 C2 C3 C9 169.5(4) . . . . ?
O1 C2 C3 C12 -67.7(5) . . . . ?
O1 C2 C3 S1 50.2(5) . . . . ?
O1 C2 N1 C8 -171.5(4) . . . . ?
O2 C18 C19 N3 -53.5(5) . . . . ?
S1 C3 C9 C4 -50.1(5) . . . . ?
S1 C3 C9 C8 127.9(3) . . . . ?
S1 C3 C12 C11 -152.1(3) . . . . ?
S1 C3 C12 C13 86.8(3) . . . . ?
S1 C3 C12 C14 -28.9(3) . . . . ?
S1 C15 N3 C16 -25.0(5) . . . . ?
S1 C15 N3 C19 173.0(3) . . . . ?


_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
;
####################################################################### 
# 
# 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_psu-1468(g-10)
_database_code_depnum_ccdc_archive 'CCDC 2288498'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-11-18
_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         'C26 H27 N3 O4 S2'
_chemical_formula_sum            'C26 H27 N3 O4 S2'
_chemical_formula_weight         509.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O 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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.539(3)
_cell_length_b                   11.4393(16)
_cell_length_c                   24.448(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5184.6(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4575
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.1880
_cell_measurement_theta_min      2.6690
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.45
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18665
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.419
_diffrn_reflns_theta_min         2.252
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00  -16.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       14.0072  -19.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega  -84.00   16.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -57.0000  -30.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0045400000
_diffrn_orient_matrix_UB_12      0.0267327000
_diffrn_orient_matrix_UB_13      -0.0259331000
_diffrn_orient_matrix_UB_21      0.0039253000
_diffrn_orient_matrix_UB_22      0.0552061000
_diffrn_orient_matrix_UB_23      0.0129050000
_diffrn_orient_matrix_UB_31      0.0377339000
_diffrn_orient_matrix_UB_32      -0.0094617000
_diffrn_orient_matrix_UB_33      0.0018455000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4136
_reflns_number_total             6274
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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         0.282
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         6274
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+2.2905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1450
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-C18 \\sim O1A-C18A
 with sigma of 0.02
 O1-C19 \\sim O1A-C19A
 with sigma of 0.02
 N2-C19 \\sim N2A-C19A
 with sigma of 0.04
 C1-N2 \\sim C1-N2A
 with sigma of 0.02
 N2-C17 \\sim N2A-C17A
 with sigma of 0.02
 N2-C20 \\sim N2A-C20A
 with sigma of 0.02
 C1-C20 \\sim C1-C20A
 with sigma of 0.04
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.04
 C1-C17 \\sim C1-C17A
 with sigma of 0.04
 N2-C18 \\sim N2A-C18A
 with sigma of 0.04
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C17-C20 \\sim C17A-C20A
 with sigma of 0.04
 O1-C17 \\sim O1A-C17A
 with sigma of 0.04
 O1-C20 \\sim O1A-C20A
 with sigma of 0.04
 C10-C14 \\sim C10A-C14A
 with sigma of 0.04
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 C11-C15 \\sim C11A-C15A
 with sigma of 0.04
 C13-C15 \\sim C13A-C15A
 with sigma of 0.04
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C10-C12 \\sim C10A-C12A
 with sigma of 0.04
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C12-C15 \\sim C12A-C15A
 with sigma of 0.02
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C12-C14 \\sim C12A-C14A
 with sigma of 0.04
 S2-C10 \\sim S2-C10A
 with sigma of 0.04
 S2-C14 \\sim S2-C14A
 with sigma of 0.04
3. Rigid bond restraints
 O1A, O1, N2, N2A, C17, C17A, C18A, C18, C19A, C19, C20A, C20
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C9, C10, C10A, C11A, C11, C12, C12A, C13, C13A, C14, C14A, C15A, C15
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
O1A \\sim O1 \\sim N2 \\sim N2A \\sim C17 \\sim C17A \\sim C18A \\sim C18 \\sim
C19A \\sim C19 \\sim C20A \\sim C20: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 1.7A
C9 \\sim C10 \\sim C10A \\sim C11A \\sim C11 \\sim C12 \\sim C12A \\sim C13
\\sim C13A \\sim C14 \\sim C14A \\sim C15A \\sim C15: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 1.7A
5. Others
 Sof(O1A)=Sof(N2A)=Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18C)=Sof(H18D)=
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20C)=1-FVAR(1)
 Sof(O1)=Sof(N2)=Sof(C17)=Sof(H17B)=Sof(H17A)=Sof(C18)=Sof(H18A)=Sof(H18B)=
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=FVAR(1)
 Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(2)
 Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(H14)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C3(H3)
6.b Secondary CH2 refined with riding coordinates:
 C17(H17B,H17A), C17A(H17C,H17D), C18A(H18C,H18D), C18(H18A,H18B), C19A(H19C,
 H19D), C19(H19A,H19B), C20A(H20D,H20C), C20(H20A,H20B)
6.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C10A(H10A), C11A(H11A), C11(H11), C13(H13), C13A(H13A), C14(H14),
 C14A(H14A), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
6.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C15A(H15D,H15E,H15F), C15(H15A,H15B,H15C)
;
_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 0.48155(4) 0.29820(5) 0.61802(2) 0.04862(18) Uani 1 1 d . . . . .
O1A O 0.3717(12) 0.6727(13) 0.5323(9) 0.082(3) Uani 0.366(7) 1 d D U P A 2
C1 C 0.42128(12) 0.32584(18) 0.56337(9) 0.0423(5) Uani 1 1 d D . . . .
O1 O 0.3571(7) 0.6717(8) 0.5415(5) 0.0737(19) Uani 0.634(7) 1 d D U P A 1
N1 N 0.32649(16) 0.2017(2) 0.45036(11) 0.0873(8) Uani 1 1 d . . . . .
C2 C 0.39535(12) 0.22580(18) 0.54034(9) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.4095(9) 0.4407(7) 0.5509(6) 0.059(3) Uani 0.634(7) 1 d D U P A 1
O2 O 0.53957(10) 0.12644(16) 0.50602(8) 0.0627(5) Uani 1 1 d . . . . .
S2 S 0.54475(4) 0.04778(6) 0.74773(3) 0.0617(2) Uani 1 1 d D . . . .
N2A N 0.4004(15) 0.4375(11) 0.5542(10) 0.046(2) Uani 0.366(7) 1 d D U P A 2
N3 N 0.52138(10) 0.11813(17) 0.68980(8) 0.0483(5) Uani 1 1 d . . . . .
O3 O 0.58112(13) 0.1352(2) 0.77898(9) 0.1026(8) Uani 1 1 d . . . . .
C3 C 0.41827(11) 0.11278(17) 0.56821(8) 0.0385(5) Uani 1 1 d . . . . .
H3 H 0.428618 0.055007 0.539667 0.046 Uiso 1 1 calc R U . . .
C4 C 0.49036(11) 0.14506(18) 0.59639(9) 0.0395(5) Uani 1 1 d . . . . .
O4 O 0.58092(10) -0.06130(19) 0.73794(9) 0.0823(7) Uani 1 1 d . . . . .
C5 C 0.55263(13) 0.1436(2) 0.55380(11) 0.0498(6) Uani 1 1 d . . . . .
C6 C 0.62724(15) 0.1641(3) 0.57414(14) 0.0877(10) Uani 1 1 d . . . . .
H6A H 0.648957 0.090728 0.583717 0.132 Uiso 1 1 calc R U . . .
H6B H 0.625612 0.213711 0.605785 0.132 Uiso 1 1 calc R U . . .
H6C H 0.655264 0.201120 0.546023 0.132 Uiso 1 1 calc R U . . .
C7 C 0.51070(11) 0.06637(19) 0.64427(10) 0.0428(5) Uani 1 1 d . . . . .
C8 C 0.51865(16) -0.0610(2) 0.62994(12) 0.0634(7) Uani 1 1 d . . . . .
H8A H 0.567428 -0.085300 0.636599 0.095 Uiso 1 1 calc R U . . .
H8B H 0.507186 -0.072264 0.592014 0.095 Uiso 1 1 calc R U . . .
H8C H 0.486415 -0.106536 0.652068 0.095 Uiso 1 1 calc R U . . .
C9 C 0.46031(14) 0.0218(2) 0.77672(10) 0.0517(6) Uani 1 1 d . U . . .
C10 C 0.4276(11) -0.0782(19) 0.7760(13) 0.055(3) Uani 0.40(2) 1 d D U P B 1
H10 H 0.450097 -0.144175 0.761795 0.066 Uiso 0.40(2) 1 calc R U P B 1
C10A C 0.4294(7) -0.0920(11) 0.7677(8) 0.050(2) Uani 0.60(2) 1 d D U P B 2
H10A H 0.454295 -0.147331 0.747255 0.061 Uiso 0.60(2) 1 calc R U P B 2
C11A C 0.3629(6) -0.1189(10) 0.7894(6) 0.0612(18) Uani 0.60(2) 1 d D U P B 2
H11A H 0.344448 -0.193975 0.785138 0.073 Uiso 0.60(2) 1 calc R U P B 2
C11 C 0.3586(10) -0.0843(16) 0.7970(10) 0.065(3) Uani 0.40(2) 1 d D U P B 1
H11 H 0.331412 -0.151904 0.792423 0.078 Uiso 0.40(2) 1 calc R U P B 1
C12 C 0.3302(8) 0.0089(19) 0.8245(8) 0.077(3) Uani 0.40(2) 1 d D U P B 1
C12A C 0.3231(5) -0.0365(12) 0.8174(5) 0.072(2) Uani 0.60(2) 1 d D U P B 2
C13 C 0.3705(10) 0.1092(16) 0.8306(9) 0.082(3) Uani 0.40(2) 1 d D U P B 1
H13 H 0.351824 0.170942 0.850882 0.099 Uiso 0.40(2) 1 calc R U P B 1
C13A C 0.3507(7) 0.0738(11) 0.8244(5) 0.082(2) Uani 0.60(2) 1 d D U P B 2
H13A H 0.324563 0.129194 0.843939 0.099 Uiso 0.60(2) 1 calc R U P B 2
C14 C 0.4365(10) 0.1200(17) 0.8078(10) 0.067(3) Uani 0.40(2) 1 d D U P B 1
H14 H 0.464460 0.186917 0.812028 0.080 Uiso 0.40(2) 1 calc R U P B 1
C14A C 0.4177(7) 0.1034(12) 0.8025(7) 0.074(3) Uani 0.60(2) 1 d D U P B 2
H14A H 0.433862 0.180072 0.805285 0.089 Uiso 0.60(2) 1 calc R U P B 2
C15A C 0.2469(6) -0.0656(17) 0.8366(6) 0.120(4) Uani 0.60(2) 1 d D U P B 2
H15D H 0.248210 -0.088623 0.874375 0.180 Uiso 0.60(2) 1 calc R U P B 2
H15E H 0.227965 -0.128578 0.814990 0.180 Uiso 0.60(2) 1 calc R U P B 2
H15F H 0.216690 0.001925 0.832596 0.180 Uiso 0.60(2) 1 calc R U P B 2
C15 C 0.2572(9) -0.003(2) 0.8530(9) 0.119(5) Uani 0.40(2) 1 d D U P B 1
H15A H 0.219744 0.024564 0.829054 0.178 Uiso 0.40(2) 1 calc R U P B 1
H15B H 0.257196 0.043288 0.885874 0.178 Uiso 0.40(2) 1 calc R U P B 1
H15C H 0.248674 -0.083191 0.862047 0.178 Uiso 0.40(2) 1 calc R U P B 1
C16 C 0.35635(14) 0.2164(2) 0.49088(10) 0.0527(6) Uani 1 1 d . . . . .
C17 C 0.3526(6) 0.4740(10) 0.5124(5) 0.076(3) Uani 0.634(7) 1 d D U P A 1
H17B H 0.317919 0.410831 0.509486 0.091 Uiso 0.634(7) 1 calc R U P A 1
H17A H 0.373588 0.486445 0.476506 0.091 Uiso 0.634(7) 1 calc R U P A 1
C17A C 0.4210(6) 0.5279(6) 0.5930(4) 0.059(2) Uani 0.366(7) 1 d D U P A 2
H17C H 0.466714 0.507713 0.609853 0.071 Uiso 0.366(7) 1 calc R U P A 2
H17D H 0.384923 0.533708 0.621612 0.071 Uiso 0.366(7) 1 calc R U P A 2
C18A C 0.4277(9) 0.6432(12) 0.5638(6) 0.081(3) Uani 0.366(7) 1 d D U P A 2
H18C H 0.434560 0.704090 0.590935 0.097 Uiso 0.366(7) 1 calc R U P A 2
H18D H 0.470624 0.641092 0.541176 0.097 Uiso 0.366(7) 1 calc R U P A 2
C18 C 0.3149(3) 0.5829(4) 0.5305(3) 0.0759(15) Uani 0.634(7) 1 d D U P A 1
H18A H 0.281414 0.606249 0.502040 0.091 Uiso 0.634(7) 1 calc R U P A 1
H18B H 0.286854 0.565023 0.562907 0.091 Uiso 0.634(7) 1 calc R U P A 1
C19A C 0.3494(6) 0.5858(7) 0.4953(5) 0.080(3) Uani 0.366(7) 1 d D U P A 2
H19C H 0.384490 0.581514 0.465902 0.096 Uiso 0.366(7) 1 calc R U P A 2
H19D H 0.303875 0.609877 0.479284 0.096 Uiso 0.366(7) 1 calc R U P A 2
C19 C 0.4089(5) 0.6424(7) 0.5827(3) 0.076(2) Uani 0.634(7) 1 d D U P A 1
H19A H 0.383924 0.625540 0.616663 0.091 Uiso 0.634(7) 1 calc R U P A 1
H19B H 0.440148 0.709155 0.588999 0.091 Uiso 0.634(7) 1 calc R U P A 1
C20A C 0.3403(11) 0.4675(16) 0.5185(9) 0.061(3) Uani 0.366(7) 1 d D U P A 2
H20D H 0.295610 0.464300 0.539130 0.073 Uiso 0.366(7) 1 calc R U P A 2
H20C H 0.337171 0.410931 0.489067 0.073 Uiso 0.366(7) 1 calc R U P A 2
C20 C 0.4542(3) 0.5390(4) 0.5671(3) 0.0587(13) Uani 0.634(7) 1 d D U P A 1
H20A H 0.485761 0.560264 0.537112 0.070 Uiso 0.634(7) 1 calc R U P A 1
H20B H 0.484073 0.516458 0.597940 0.070 Uiso 0.634(7) 1 calc R U P A 1
C21 C 0.36144(11) 0.06128(19) 0.60619(9) 0.0412(5) Uani 1 1 d . . . . .
C22 C 0.32946(13) 0.1256(2) 0.64792(10) 0.0547(6) Uani 1 1 d . . . . .
H22 H 0.343523 0.202534 0.654066 0.066 Uiso 1 1 calc R U . . .
C23 C 0.27664(15) 0.0751(3) 0.68036(11) 0.0687(8) Uani 1 1 d . . . . .
H23 H 0.255144 0.118750 0.708014 0.082 Uiso 1 1 calc R U . . .
C24 C 0.25574(16) -0.0388(3) 0.67203(13) 0.0757(9) Uani 1 1 d . . . . .
H24 H 0.220181 -0.072023 0.693890 0.091 Uiso 1 1 calc R U . . .
C25 C 0.28752(15) -0.1030(3) 0.63141(14) 0.0732(8) Uani 1 1 d . . . . .
H25 H 0.273930 -0.180408 0.625989 0.088 Uiso 1 1 calc R U . . .
C26 C 0.33966(13) -0.0534(2) 0.59843(11) 0.0548(6) Uani 1 1 d . . . . .
H26 H 0.360443 -0.097517 0.570644 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.770(2) . ?
S1 C4 1.837(2) . ?
O1A C18A 1.334(19) . ?
O1A C19A 1.407(19) . ?
C1 C2 1.363(3) . ?
C1 N2 1.366(7) . ?
C1 N2A 1.354(11) . ?
O1 C18 1.309(12) . ?
O1 C19 1.433(12) . ?
N1 C16 1.147(3) . ?
C2 C3 1.522(3) . ?
C2 C16 1.413(3) . ?
N2 C17 1.464(14) . ?
N2 C20 1.451(14) . ?
O2 C5 1.209(3) . ?
S2 N3 1.6856(19) . ?
S2 O3 1.427(2) . ?
S2 O4 1.437(2) . ?
S2 C9 1.744(3) . ?
N2A C17A 1.45(2) . ?
N2A C20A 1.46(2) . ?
N3 C7 1.276(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.548(3) . ?
C3 C21 1.523(3) . ?
C4 C5 1.555(3) . ?
C4 C7 1.524(3) . ?
C5 C6 1.488(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.505(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.294(18) . ?
C9 C10A 1.439(12) . ?
C9 C14 1.426(17) . ?
C9 C14A 1.375(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(12) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.377(8) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.378(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(12) . ?
C12 C13 1.377(12) . ?
C12 C15 1.529(12) . ?
C12A C13A 1.372(9) . ?
C12A C15A 1.525(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.350(12) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.394(9) . ?
C14 H14 0.9300 . ?
C14A H14A 0.9300 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 C18 1.496(13) . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C17A C18A 1.506(15) . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C19A C20A 1.477(17) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.499(10) . ?
C20A H20D 0.9700 . ?
C20A H20C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.391(3) . ?
C21 C26 1.385(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.369(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(4) . ?
C26 H26 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
C1 S1 C4 90.52(10) . . ?
C18A O1A C19A 114.9(12) . . ?
C2 C1 S1 112.61(16) . . ?
C2 C1 N2 131.3(7) . . ?
N2 C1 S1 116.1(7) . . ?
N2A C1 S1 118.3(11) . . ?
N2A C1 C2 128.5(11) . . ?
C18 O1 C19 111.3(8) . . ?
C1 C2 C3 115.45(18) . . ?
C1 C2 C16 126.7(2) . . ?
C16 C2 C3 117.49(18) . . ?
C1 N2 C17 120.5(11) . . ?
C1 N2 C20 126.4(11) . . ?
C20 N2 C17 112.7(6) . . ?
N3 S2 C9 101.08(10) . . ?
O3 S2 N3 103.70(12) . . ?
O3 S2 O4 118.49(15) . . ?
O3 S2 C9 109.01(15) . . ?
O4 S2 N3 113.25(12) . . ?
O4 S2 C9 109.80(12) . . ?
C1 N2A C17A 119.2(17) . . ?
C1 N2A C20A 122.7(18) . . ?
C17A N2A C20A 115.1(12) . . ?
C7 N3 S2 123.45(17) . . ?
C2 C3 H3 108.0 . . ?
C2 C3 C4 103.75(16) . . ?
C2 C3 C21 114.11(18) . . ?
C4 C3 H3 108.0 . . ?
C21 C3 H3 108.0 . . ?
C21 C3 C4 114.71(17) . . ?
C3 C4 S1 106.19(14) . . ?
C3 C4 C5 109.89(18) . . ?
C5 C4 S1 105.61(14) . . ?
C7 C4 S1 111.35(15) . . ?
C7 C4 C3 114.49(17) . . ?
C7 C4 C5 108.92(17) . . ?
O2 C5 C4 120.0(2) . . ?
O2 C5 C6 122.3(2) . . ?
C6 C5 C4 117.7(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 C4 115.74(19) . . ?
N3 C7 C8 129.5(2) . . ?
C8 C7 C4 114.6(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 S2 124.4(8) . . ?
C10 C9 C14 123.9(10) . . ?
C10A C9 S2 116.7(4) . . ?
C14 C9 S2 111.1(7) . . ?
C14A C9 S2 125.9(5) . . ?
C14A C9 C10A 117.0(6) . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.3(13) . . ?
C11 C10 H10 120.9 . . ?
C9 C10A H10A 120.0 . . ?
C11A C10A C9 120.0(8) . . ?
C11A C10A H10A 120.0 . . ?
C10A C11A H11A 119.4 . . ?
C10A C11A C12A 121.1(7) . . ?
C12A C11A H11A 119.4 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(12) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.6(10) . . ?
C11 C12 C15 119.9(12) . . ?
C13 C12 C15 120.3(11) . . ?
C11A C12A C15A 119.9(7) . . ?
C13A C12A C11A 119.4(6) . . ?
C13A C12A C15A 120.5(7) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.6(11) . . ?
C14 C13 H13 119.2 . . ?
C12A C13A H13A 119.8 . . ?
C12A C13A C14A 120.5(7) . . ?
C14A C13A H13A 119.8 . . ?
C9 C14 H14 122.3 . . ?
C13 C14 C9 115.3(11) . . ?
C13 C14 H14 122.3 . . ?
C9 C14A C13A 121.6(8) . . ?
C9 C14A H14A 119.2 . . ?
C13A C14A H14A 119.2 . . ?
C12A C15A H15D 109.5 . . ?
C12A C15A H15E 109.5 . . ?
C12A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C2 175.6(3) . . ?
N2 C17 H17B 109.4 . . ?
N2 C17 H17A 109.4 . . ?
N2 C17 C18 111.3(9) . . ?
H17B C17 H17A 108.0 . . ?
C18 C17 H17B 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N2A C17A H17C 109.8 . . ?
N2A C17A H17D 109.8 . . ?
N2A C17A C18A 109.6(11) . . ?
H17C C17A H17D 108.2 . . ?
C18A C17A H17C 109.8 . . ?
C18A C17A H17D 109.8 . . ?
O1A C18A C17A 115.5(12) . . ?
O1A C18A H18C 108.4 . . ?
O1A C18A H18D 108.4 . . ?
C17A C18A H18C 108.4 . . ?
C17A C18A H18D 108.4 . . ?
H18C C18A H18D 107.5 . . ?
O1 C18 C17 115.4(7) . . ?
O1 C18 H18A 108.4 . . ?
O1 C18 H18B 108.4 . . ?
C17 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
O1A C19A H19C 108.4 . . ?
O1A C19A H19D 108.4 . . ?
O1A C19A C20A 115.7(12) . . ?
H19C C19A H19D 107.4 . . ?
C20A C19A H19C 108.4 . . ?
C20A C19A H19D 108.4 . . ?
O1 C19 H19A 109.1 . . ?
O1 C19 H19B 109.1 . . ?
O1 C19 C20 112.4(6) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
N2A C20A C19A 111.0(13) . . ?
N2A C20A H20D 109.4 . . ?
N2A C20A H20C 109.4 . . ?
C19A C20A H20D 109.4 . . ?
C19A C20A H20C 109.4 . . ?
H20D C20A H20C 108.0 . . ?
N2 C20 C19 111.2(7) . . ?
N2 C20 H20A 109.4 . . ?
N2 C20 H20B 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C3 122.5(2) . . ?
C26 C21 C3 119.0(2) . . ?
C26 C21 C22 118.5(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.3(3) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.9(3) . . ?
C25 C26 H26 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 4.3(3) . . . . ?
S1 C1 C2 C16 -168.6(2) . . . . ?
S1 C1 N2 C17 -170.5(10) . . . . ?
S1 C1 N2 C20 17.5(17) . . . . ?
S1 C1 N2A C17A -7(3) . . . . ?
S1 C1 N2A C20A -166.7(17) . . . . ?
S1 C4 C5 O2 -109.6(2) . . . . ?
S1 C4 C5 C6 70.2(2) . . . . ?
S1 C4 C7 N3 -3.0(2) . . . . ?
S1 C4 C7 C8 179.73(17) . . . . ?
O1A C19A C20A N2A -45(2) . . . . ?
C1 S1 C4 C3 -28.91(15) . . . . ?
C1 S1 C4 C5 87.77(16) . . . . ?
C1 S1 C4 C7 -154.15(16) . . . . ?
C1 C2 C3 C4 -25.6(2) . . . . ?
C1 C2 C3 C21 99.9(2) . . . . ?
C1 N2 C17 C18 141.2(12) . . . . ?
C1 N2 C20 C19 -140.2(13) . . . . ?
C1 N2A C17A C18A 150.9(18) . . . . ?
C1 N2A C20A C19A -153(2) . . . . ?
O1 C19 C20 N2 -51.9(11) . . . . ?
C2 C1 N2 C17 10.6(19) . . . . ?
C2 C1 N2 C20 -161.3(8) . . . . ?
C2 C1 N2A C17A 163.6(12) . . . . ?
C2 C1 N2A C20A 4(3) . . . . ?
C2 C3 C4 S1 34.13(18) . . . . ?
C2 C3 C4 C5 -79.6(2) . . . . ?
C2 C3 C4 C7 157.41(18) . . . . ?
C2 C3 C21 C22 -53.3(3) . . . . ?
C2 C3 C21 C26 125.5(2) . . . . ?
N2 C1 C2 C3 -176.8(10) . . . . ?
N2 C1 C2 C16 10.2(11) . . . . ?
N2 C17 C18 O1 52.2(13) . . . . ?
S2 N3 C7 C4 -179.66(15) . . . . ?
S2 N3 C7 C8 -2.9(4) . . . . ?
S2 C9 C10 C11 -175.3(16) . . . . ?
S2 C9 C10A C11A 179.9(12) . . . . ?
S2 C9 C14 C13 178.2(15) . . . . ?
S2 C9 C14A C13A -180.0(9) . . . . ?
N2A C1 C2 C3 -166.9(15) . . . . ?
N2A C1 C2 C16 20.1(15) . . . . ?
N2A C17A C18A O1A 50(2) . . . . ?
N3 S2 C9 C10 103.0(19) . . . . ?
N3 S2 C9 C10A 97.5(10) . . . . ?
N3 S2 C9 C14 -85.1(12) . . . . ?
N3 S2 C9 C14A -75.4(10) . . . . ?
O3 S2 N3 C7 155.0(2) . . . . ?
O3 S2 C9 C10 -148.2(19) . . . . ?
O3 S2 C9 C10A -153.7(10) . . . . ?
O3 S2 C9 C14 23.7(12) . . . . ?
O3 S2 C9 C14A 33.4(10) . . . . ?
C3 C4 C5 O2 4.5(3) . . . . ?
C3 C4 C5 C6 -175.7(2) . . . . ?
C3 C4 C7 N3 -123.5(2) . . . . ?
C3 C4 C7 C8 59.3(3) . . . . ?
C3 C21 C22 C23 178.3(2) . . . . ?
C3 C21 C26 C25 -179.0(2) . . . . ?
C4 S1 C1 C2 15.00(19) . . . . ?
C4 S1 C1 N2 -164.0(8) . . . . ?
C4 S1 C1 N2A -172.8(13) . . . . ?
C4 C3 C21 C22 66.2(3) . . . . ?
C4 C3 C21 C26 -115.0(2) . . . . ?
O4 S2 N3 C7 25.2(2) . . . . ?
O4 S2 C9 C10 -16.9(19) . . . . ?
O4 S2 C9 C10A -22.4(10) . . . . ?
O4 S2 C9 C14 155.0(12) . . . . ?
O4 S2 C9 C14A 164.7(10) . . . . ?
C5 C4 C7 N3 113.0(2) . . . . ?
C5 C4 C7 C8 -64.2(2) . . . . ?
C7 C4 C5 O2 130.7(2) . . . . ?
C7 C4 C5 C6 -49.5(3) . . . . ?
C9 S2 N3 C7 -92.1(2) . . . . ?
C9 C10 C11 C12 -9(4) . . . . ?
C9 C10A C11A C12A 4(2) . . . . ?
C10 C9 C14 C13 -10(3) . . . . ?
C10 C11 C12 C13 1(3) . . . . ?
C10 C11 C12 C15 -173(2) . . . . ?
C10A C9 C14A C13A 7(2) . . . . ?
C10A C11A C12A C13A -1(2) . . . . ?
C10A C11A C12A C15A 174.7(15) . . . . ?
C11A C12A C13A C14A 1.4(18) . . . . ?
C11 C12 C13 C14 3(3) . . . . ?
C12 C13 C14 C9 1(3) . . . . ?
C12A C13A C14A C9 -5(2) . . . . ?
C14 C9 C10 C11 14(4) . . . . ?
C14A C9 C10A C11A -6(2) . . . . ?
C15A C12A C13A C14A -174.1(12) . . . . ?
C15 C12 C13 C14 177(2) . . . . ?
C16 C2 C3 C4 148.0(2) . . . . ?
C16 C2 C3 C21 -86.5(2) . . . . ?
C17 N2 C20 C19 47.3(14) . . . . ?
C17A N2A C20A C19A 46(3) . . . . ?
C18A O1A C19A C20A 48(2) . . . . ?
C18 O1 C19 C20 57.0(11) . . . . ?
C19A O1A C18A C17A -51(2) . . . . ?
C19 O1 C18 C17 -57.2(11) . . . . ?
C20A N2A C17A C18A -48(2) . . . . ?
C20 N2 C17 C18 -45.8(15) . . . . ?
C21 C3 C4 S1 -91.00(18) . . . . ?
C21 C3 C4 C5 155.22(18) . . . . ?
C21 C3 C4 C7 32.3(2) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C22 C21 C26 C25 -0.2(4) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C23 C24 C25 C26 -0.8(5) . . . . ?
C24 C25 C26 C21 0.8(4) . . . . ?
C26 C21 C22 C23 -0.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_psu-1422(g-25)
_database_code_depnum_ccdc_archive 'CCDC 2288497'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-29
_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         'C14 H13 Cl N2 O2 S'
_chemical_formula_sum            'C14 H13 Cl N2 O2 S'
_chemical_formula_weight         308.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H Cl N O 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'
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                   13.453(3)
_cell_length_b                   9.8748(18)
_cell_length_c                   11.570(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.97(3)
_cell_angle_gamma                90
_cell_volume                     1462.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2473
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.8970
_cell_measurement_theta_min      2.6660
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7161
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.494
_diffrn_reflns_theta_min         2.605
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   70.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       14.1634   57.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -68.00   18.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       14.1634  -77.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -99.0000 -180.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0491227000
_diffrn_orient_matrix_UB_12      -0.0017585000
_diffrn_orient_matrix_UB_13      -0.0460162000
_diffrn_orient_matrix_UB_21      0.0255176000
_diffrn_orient_matrix_UB_22      -0.0062188000
_diffrn_orient_matrix_UB_23      -0.0449434000
_diffrn_orient_matrix_UB_31      -0.0009348000
_diffrn_orient_matrix_UB_32      -0.0715956000
_diffrn_orient_matrix_UB_33      0.0049991000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2725
_reflns_number_total             3480
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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         0.455
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.055(3)
_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   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+0.5491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1446
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.66395(4) 0.74604(5) 0.67079(5) 0.03064(19) Uani 1 1 d . . . . .
C1 C 0.53602(16) 0.7937(2) 0.46674(19) 0.0305(4) Uani 1 1 d . . . . .
H1 H 0.548786 0.703511 0.452951 0.037 Uiso 1 1 calc R U . . .
N1 N 0.58435(13) 0.84742(16) 0.57315(16) 0.0313(4) Uani 1 1 d . . . . .
Cl1 Cl 0.21209(6) 0.65315(7) -0.09806(6) 0.0600(3) Uani 1 1 d . . . . .
O1 O 0.65105(13) 0.77036(17) 0.78782(14) 0.0416(4) Uani 1 1 d . . . . .
N2 N 0.46994(14) 0.86345(19) 0.37874(17) 0.0328(4) Uani 1 1 d . . . . .
H2 H 0.4585(18) 0.951(3) 0.391(2) 0.037(6) Uiso 1 1 d . . . . .
C2 C 0.41240(15) 0.8087(2) 0.26411(18) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.65391(13) 0.60897(15) 0.62689(16) 0.0447(4) Uani 1 1 d . . . . .
C3 C 0.37631(18) 0.8967(2) 0.1671(2) 0.0377(5) Uani 1 1 d . . . . .
H3 H 0.392871 0.988290 0.177443 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3155(2) 0.8494(2) 0.0544(2) 0.0424(6) Uani 1 1 d . . . . .
H4 H 0.290808 0.908542 -0.010717 0.051 Uiso 1 1 calc R U . . .
C5 C 0.29250(18) 0.7129(2) 0.0408(2) 0.0375(5) Uani 1 1 d . . . . .
C6 C 0.32997(17) 0.6241(2) 0.1356(2) 0.0377(5) Uani 1 1 d . . . . .
H6 H 0.315434 0.532110 0.124104 0.045 Uiso 1 1 calc R U . . .
C7 C 0.38950(17) 0.6717(2) 0.2485(2) 0.0350(5) Uani 1 1 d . . . . .
H7 H 0.413939 0.612092 0.313288 0.042 Uiso 1 1 calc R U . . .
C8 C 0.78878(16) 0.8033(2) 0.67715(19) 0.0324(5) Uani 1 1 d . . . . .
C9 C 0.84773(18) 0.8762(3) 0.7768(2) 0.0444(6) Uani 1 1 d . . . . .
H9 H 0.821354 0.895773 0.840367 0.053 Uiso 1 1 calc R U . . .
C10 C 0.9466(2) 0.9195(3) 0.7807(3) 0.0584(7) Uani 1 1 d . . . . .
H10 H 0.986778 0.968366 0.847561 0.070 Uiso 1 1 calc R U . . .
C11 C 0.98621(19) 0.8913(3) 0.6868(3) 0.0566(7) Uani 1 1 d . . . . .
C12 C 0.9256(2) 0.8182(3) 0.5886(3) 0.0594(8) Uani 1 1 d . . . . .
H12 H 0.951957 0.798236 0.525133 0.071 Uiso 1 1 calc R U . . .
C13 C 0.8271(2) 0.7744(3) 0.5823(2) 0.0485(6) Uani 1 1 d . . . . .
H13 H 0.786946 0.725982 0.515192 0.058 Uiso 1 1 calc R U . . .
C14 C 1.0922(2) 0.9425(4) 0.6892(4) 0.0914(13) Uani 1 1 d . . . . .
H14A H 1.084206 1.012636 0.629571 0.137 Uiso 1 1 calc R U . . .
H14B H 1.132141 0.869389 0.671280 0.137 Uiso 1 1 calc R U . . .
H14C H 1.127945 0.978157 0.768362 0.137 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.6366(18) . ?
S1 O1 1.4375(16) . ?
S1 O2 1.4373(17) . ?
S1 C8 1.752(2) . ?
C1 H1 0.9300 . ?
C1 N1 1.314(3) . ?
C1 N2 1.320(3) . ?
Cl1 C5 1.740(2) . ?
N2 H2 0.89(2) . ?
N2 C2 1.420(3) . ?
C2 C3 1.384(3) . ?
C2 C7 1.387(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 C6 1.373(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(3) . ?
C8 C13 1.378(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(4) . ?
C11 C12 1.380(4) . ?
C11 C14 1.505(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
N1 S1 C8 104.24(10) . . ?
O1 S1 N1 107.73(10) . . ?
O1 S1 C8 107.41(11) . . ?
O2 S1 N1 111.23(10) . . ?
O2 S1 O1 117.69(10) . . ?
O2 S1 C8 107.66(10) . . ?
N1 C1 H1 118.9 . . ?
N1 C1 N2 122.19(19) . . ?
N2 C1 H1 118.9 . . ?
C1 N1 S1 115.40(14) . . ?
C1 N2 H2 119.0(15) . . ?
C1 N2 C2 124.38(19) . . ?
C2 N2 H2 116.6(15) . . ?
C3 C2 N2 118.15(19) . . ?
C3 C2 C7 119.9(2) . . ?
C7 C2 N2 121.91(19) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Cl1 119.35(19) . . ?
C6 C5 Cl1 119.44(18) . . ?
C6 C5 C4 121.2(2) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.9(2) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 120.2 . . ?
C6 C7 C2 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C9 C8 S1 119.91(17) . . ?
C13 C8 S1 119.26(18) . . ?
C13 C8 C9 120.8(2) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 118.7(2) . . ?
C10 C11 C14 120.8(3) . . ?
C12 C11 C14 120.4(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.2 . . ?
C8 C13 H13 120.5 . . ?
C12 C13 C8 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 N1 0.89(2) 2.15(3) 3.041(3) 173(2) 3_676 yes

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 C8 C9 C10 179.4(2) . . . . ?
S1 C8 C13 C12 -179.2(2) . . . . ?
C1 N2 C2 C3 -157.3(2) . . . . ?
C1 N2 C2 C7 24.6(3) . . . . ?
N1 S1 C8 C9 105.15(19) . . . . ?
N1 S1 C8 C13 -75.1(2) . . . . ?
N1 C1 N2 C2 -177.18(18) . . . . ?
Cl1 C5 C6 C7 -176.56(17) . . . . ?
O1 S1 N1 C1 -139.16(16) . . . . ?
O1 S1 C8 C9 -9.0(2) . . . . ?
O1 S1 C8 C13 170.74(19) . . . . ?
N2 C1 N1 S1 -179.63(16) . . . . ?
N2 C2 C3 C4 -177.0(2) . . . . ?
N2 C2 C7 C6 177.77(19) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
O2 S1 N1 C1 -8.80(18) . . . . ?
O2 S1 C8 C9 -136.64(19) . . . . ?
O2 S1 C8 C13 43.1(2) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
C3 C4 C5 Cl1 177.40(19) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C7 2.0(3) . . . . ?
C5 C6 C7 C2 -1.2(3) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
C8 S1 N1 C1 106.94(16) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C8 C13 C12 0.5(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C9 C10 C11 C14 177.9(3) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C8 -0.6(4) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C14 C11 C12 C13 -177.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_42
_database_code_depnum_ccdc_archive 'CCDC 2288491'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-04-11
_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         'C24 H23 N3 O3 S'
_chemical_formula_sum            'C24 H23 N3 O3 S'
_chemical_formula_weight         433.51
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.4556(12)
_cell_length_b                   16.0823(15)
_cell_length_c                   21.045(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4554.0(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2121
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.4410
_cell_measurement_theta_min      3.8470
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0885
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14386
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.812
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  44.00   1.00   20.00    --   21.29-105.00 -42.00   31
  2  ω    -45.00  37.00   1.00   20.00    --  -22.85  39.00-155.00   82
  3  ω    -29.00  -3.00   1.00   20.00    --  -22.85 -77.00-180.00   26
  4  ω    -38.00   6.00   1.00   20.00    --  -22.85 -77.00  60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2121
_reflns_number_total             4622
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.210
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.1549
_refine_ls_R_factor_gt           0.0672
_refine_ls_restrained_S_all      1.028
_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)+(0.0914P)²+0.0761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.2266
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-C22
 1.54 with sigma of 0.02
 C22A-C21A
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C24A) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C23A)
\\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(C22A) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C21) = Uanis(C21A)
4. Others
 Fixed Sof: O2(0.75) C21(0.65) H21A(0.65) H21B(0.65) C24(0.75) H24A(0.75)
 H24B(0.75) C22(0.65) H22A(0.65) H22B(0.65) C23(0.75) H23A(0.75) H23B(0.75)
 O2A(0.25) C23A(0.25) H23C(0.25) H23D(0.25) C22A(0.35) H22C(0.35) H22D(0.35)
 C24A(0.25) H24C(0.25) H24D(0.25) C21A(0.35) H21C(0.35) H21D(0.35)
5.a Ternary CH refined with riding coordinates:
 C4(H4A)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C24(H24A,H24B), C22(H22A,H22B), C23(H23A,H23B), C23A(H23C,
 H23D), C22A(H22C,H22D), C24A(H24C,H24D), C21A(H21C,H21D)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C18(H18), C16(H16), C17(H17)
5.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.35748(7) 0.51061(6) 0.61115(5) 0.0645(4) Uani 1 1 d . . . . .
O1 O 0.51146(19) 0.57697(19) 0.53387(14) 0.0788(9) Uani 1 1 d . . . . .
N4 N 0.2820(2) 0.4769(2) 0.47567(15) 0.0591(9) Uani 1 1 d . . . . .
O3 O 0.1820(2) 0.5870(2) 0.49199(19) 0.1119(14) Uani 1 1 d . . . . .
N1 N 0.2282(3) 0.5101(2) 0.70670(17) 0.0763(10) Uani 1 1 d . . . . .
C3 C 0.2382(2) 0.6331(2) 0.63738(18) 0.0559(9) Uani 1 1 d . . . . .
C6 C 0.2581(3) 0.5505(2) 0.50221(18) 0.0600(10) Uani 1 1 d . . . . .
C13 C 0.3741(3) 0.7285(2) 0.59902(16) 0.0541(9) Uani 1 1 d . . . . .
C5 C 0.3369(2) 0.5861(2) 0.54815(17) 0.0519(9) Uani 1 1 d . . . . .
C7 C 0.2250(3) 0.4274(2) 0.43387(18) 0.0601(10) Uani 1 1 d . . . . .
C4 C 0.2960(2) 0.6650(2) 0.58122(17) 0.0550(9) Uani 1 1 d . . . . .
H4A H 0.249038 0.691707 0.552077 0.066 Uiso 1 1 calc R U . . .
C14 C 0.4391(3) 0.7169(3) 0.64931(18) 0.0642(10) Uani 1 1 d . . . . .
H14 H 0.433682 0.668917 0.673744 0.077 Uiso 1 1 calc R U . . .
C19 C 0.4345(3) 0.6026(3) 0.51275(19) 0.0615(10) Uani 1 1 d . . . . .
C2 C 0.2636(3) 0.5557(2) 0.65795(18) 0.0586(10) Uani 1 1 d . . . . .
C1 C 0.1729(3) 0.6900(3) 0.6662(2) 0.0730(12) Uani 1 1 d . . . . .
C12 C 0.2698(4) 0.3563(3) 0.4113(2) 0.0780(13) Uani 1 1 d . . . . .
N2 N 0.1219(3) 0.7416(3) 0.6853(2) 0.1091(15) Uani 1 1 d . . . . .
C8 C 0.1281(4) 0.4447(3) 0.4183(3) 0.0827(14) Uani 1 1 d . . . . .
C15 C 0.5105(3) 0.7734(3) 0.6640(2) 0.0790(13) Uani 1 1 d . . . . .
H15 H 0.552966 0.763542 0.698030 0.095 Uiso 1 1 calc R U . . .
O2 O 0.1657(6) 0.4151(6) 0.8114(3) 0.126(2) Uani 0.75 1 d . U P A 1
C11 C 0.2181(5) 0.3044(4) 0.3712(3) 0.1005(18) Uani 1 1 d . . . . .
C10 C 0.1233(5) 0.3219(4) 0.3540(3) 0.105(2) Uani 1 1 d . . . . .
C9 C 0.0791(5) 0.3914(4) 0.3774(3) 0.1051(19) Uani 1 1 d . . . . .
C18 C 0.3847(4) 0.8004(3) 0.5656(2) 0.1067(18) Uani 1 1 d . . . . .
H18 H 0.342010 0.810641 0.531770 0.128 Uiso 1 1 calc R U . . .
C20 C 0.4277(4) 0.6498(3) 0.4528(2) 0.0996(16) Uani 1 1 d . . . . .
H20A H 0.489630 0.677598 0.444911 0.149 Uiso 1 1 calc R U . . .
H20B H 0.375422 0.690214 0.456044 0.149 Uiso 1 1 calc R U . . .
H20C H 0.413598 0.612357 0.418450 0.149 Uiso 1 1 calc R U . . .
C16 C 0.5203(4) 0.8441(4) 0.6293(3) 0.1132(19) Uani 1 1 d . . . . .
H16 H 0.569877 0.882487 0.638852 0.136 Uiso 1 1 calc R U . . .
C21 C 0.1725(9) 0.5430(9) 0.7584(7) 0.104(3) Uani 0.65 1 d D U P A 1
H21A H 0.136800 0.592383 0.744898 0.124 Uiso 0.65 1 calc R U P A 1
H21B H 0.216743 0.558291 0.792825 0.124 Uiso 0.65 1 calc R U P A 1
C24 C 0.2850(6) 0.4385(5) 0.7303(4) 0.092(2) Uani 0.75 1 d . U P A 1
H24A H 0.329509 0.455718 0.764138 0.110 Uiso 0.75 1 calc R U P A 1
H24B H 0.324409 0.414541 0.696328 0.110 Uiso 0.75 1 calc R U P A 1
C17 C 0.4558(5) 0.8579(4) 0.5801(3) 0.151(3) Uani 1 1 d . . . . .
H17 H 0.460429 0.906558 0.556386 0.181 Uiso 1 1 calc R U . . .
C22 C 0.0968(10) 0.4746(10) 0.7815(8) 0.129(5) Uani 0.65 1 d D U P A 1
H22A H 0.049568 0.496777 0.811918 0.155 Uiso 0.65 1 calc R U P A 1
H22B H 0.061240 0.449698 0.746228 0.155 Uiso 0.65 1 calc R U P A 1
C23 C 0.2090(9) 0.3739(6) 0.7556(5) 0.113(3) Uani 0.75 1 d . U P A 1
H23A H 0.158493 0.361912 0.723994 0.135 Uiso 0.75 1 calc R U P A 1
H23B H 0.241776 0.322428 0.767461 0.135 Uiso 0.75 1 calc R U P A 1
O2A O 0.1247(18) 0.4047(17) 0.7857(13) 0.126(8) Uani 0.25 1 d . U P A 2
C23A C 0.237(3) 0.395(3) 0.778(2) 0.128(15) Uani 0.25 1 d . U P A 2
H23C H 0.259847 0.338845 0.784855 0.154 Uiso 0.25 1 calc R U P A 2
H23D H 0.274480 0.433726 0.803995 0.154 Uiso 0.25 1 calc R U P A 2
C22A C 0.1275(19) 0.4919(15) 0.8011(10) 0.099(7) Uani 0.35 1 d D U P A 2
H22C H 0.181269 0.501034 0.831052 0.119 Uiso 0.35 1 calc R U P A 2
H22D H 0.066006 0.506253 0.822493 0.119 Uiso 0.35 1 calc R U P A 2
C24A C 0.239(2) 0.420(2) 0.7057(14) 0.123(10) Uani 0.25 1 d . U P A 2
H24C H 0.301143 0.403834 0.685934 0.148 Uiso 0.25 1 calc R U P A 2
H24D H 0.184431 0.394126 0.682871 0.148 Uiso 0.25 1 calc R U P A 2
C21A C 0.142(2) 0.5510(19) 0.7452(13) 0.104(3) Uani 0.35 1 d D U P A 2
H21C H 0.159676 0.606253 0.759700 0.124 Uiso 0.35 1 calc R U P A 2
H21D H 0.081501 0.554714 0.719854 0.124 Uiso 0.35 1 calc R U P A 2
H12 H 0.338(3) 0.343(3) 0.423(2) 0.090(14) Uiso 1 1 d . . . . .
H8 H 0.098(3) 0.490(3) 0.438(2) 0.088(15) Uiso 1 1 d . . . . .
H9 H 0.005(3) 0.398(3) 0.369(2) 0.108(16) Uiso 1 1 d . . . . .
H11 H 0.259(4) 0.254(4) 0.358(3) 0.13(2) Uiso 1 1 d . . . . .
H4 H 0.344(4) 0.462(3) 0.484(3) 0.118(19) Uiso 1 1 d . . . . .
H10 H 0.093(4) 0.289(3) 0.325(2) 0.109(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.819(4) . ?
S1 C2 1.758(4) . ?
O1 C19 1.199(4) . ?
N4 C6 1.348(5) . ?
N4 C7 1.412(4) . ?
N4 H4 0.89(5) . ?
O3 C6 1.199(4) . ?
N1 C2 1.348(5) . ?
N1 C21 1.423(15) . ?
N1 C24 1.469(8) . ?
N1 C24A 1.46(3) . ?
N1 C21A 1.57(3) . ?
C3 C4 1.505(5) . ?
C3 C2 1.362(5) . ?
C3 C1 1.406(6) . ?
C6 C5 1.545(5) . ?
C13 C4 1.513(5) . ?
C13 C14 1.386(5) . ?
C13 C18 1.359(5) . ?
C5 C4 1.549(5) . ?
C5 C19 1.533(5) . ?
C7 C12 1.377(5) . ?
C7 C8 1.374(6) . ?
C4 H4A 0.9800 . ?
C14 H14 0.9300 . ?
C14 C15 1.358(5) . ?
C19 C20 1.475(6) . ?
C1 N2 1.150(5) . ?
C12 C11 1.377(6) . ?
C12 H12 0.97(4) . ?
C8 C9 1.381(7) . ?
C8 H8 0.92(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.358(6) . ?
O2 C22 1.472(17) . ?
O2 C23 1.470(14) . ?
C11 C10 1.355(8) . ?
C11 H11 1.02(6) . ?
C10 C9 1.359(8) . ?
C10 H10 0.90(5) . ?
C9 H9 1.02(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.365(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.371(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.577(13) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C23 1.553(12) . ?
C17 H17 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
O2A C23A 1.53(5) . ?
O2A C22A 1.44(4) . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C23A C24A 1.57(5) . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C21A 1.524(18) . ?
C24A H24C 0.9700 . ?
C24A H24D 0.9700 . ?
C21A H21C 0.9700 . ?
C21A H21D 0.9700 . ?

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 C5 91.38(17) . . ?
C6 N4 C7 128.6(3) . . ?
C6 N4 H4 113(4) . . ?
C7 N4 H4 119(4) . . ?
C2 N1 C21 124.4(6) . . ?
C2 N1 C24 120.0(4) . . ?
C2 N1 C24A 119.7(12) . . ?
C2 N1 C21A 115.4(9) . . ?
C21 N1 C24 107.9(6) . . ?
C24A N1 C21A 120.0(16) . . ?
C2 C3 C4 115.6(3) . . ?
C2 C3 C1 127.9(4) . . ?
C1 C3 C4 116.1(3) . . ?
N4 C6 C5 114.9(3) . . ?
O3 C6 N4 124.0(4) . . ?
O3 C6 C5 121.1(3) . . ?
C14 C13 C4 122.4(3) . . ?
C18 C13 C4 121.2(3) . . ?
C18 C13 C14 116.4(4) . . ?
C6 C5 S1 108.3(3) . . ?
C6 C5 C4 109.9(3) . . ?
C4 C5 S1 105.9(2) . . ?
C19 C5 S1 109.9(2) . . ?
C19 C5 C6 110.4(3) . . ?
C19 C5 C4 112.4(3) . . ?
C12 C7 N4 116.5(4) . . ?
C8 C7 N4 123.3(4) . . ?
C8 C7 C12 120.1(4) . . ?
C3 C4 C13 113.3(3) . . ?
C3 C4 C5 104.9(3) . . ?
C3 C4 H4A 107.9 . . ?
C13 C4 C5 114.7(3) . . ?
C13 C4 H4A 107.9 . . ?
C5 C4 H4A 107.9 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.0(4) . . ?
C15 C14 H14 119.0 . . ?
O1 C19 C5 120.0(4) . . ?
O1 C19 C20 123.2(4) . . ?
C20 C19 C5 116.8(4) . . ?
N1 C2 S1 117.1(3) . . ?
N1 C2 C3 130.6(4) . . ?
C3 C2 S1 112.3(3) . . ?
N2 C1 C3 173.5(5) . . ?
C7 C12 H12 121(3) . . ?
C11 C12 C7 119.6(5) . . ?
C11 C12 H12 119(3) . . ?
C7 C8 C9 118.4(5) . . ?
C7 C8 H8 118(3) . . ?
C9 C8 H8 123(3) . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C23 O2 C22 101.6(9) . . ?
C12 C11 H11 112(3) . . ?
C10 C11 C12 120.8(6) . . ?
C10 C11 H11 127(3) . . ?
C11 C10 C9 119.2(6) . . ?
C11 C10 H10 118(3) . . ?
C9 C10 H10 122(3) . . ?
C8 C9 H9 121(3) . . ?
C10 C9 C8 121.8(6) . . ?
C10 C9 H9 117(3) . . ?
C13 C18 H18 118.9 . . ?
C13 C18 C17 122.3(4) . . ?
C17 C18 H18 118.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.7(5) . . ?
C17 C16 H16 120.7 . . ?
N1 C21 H21A 110.0 . . ?
N1 C21 H21B 110.0 . . ?
N1 C21 C22 108.4(12) . . ?
H21A C21 H21B 108.4 . . ?
C22 C21 H21A 110.0 . . ?
C22 C21 H21B 110.0 . . ?
N1 C24 H24A 110.3 . . ?
N1 C24 H24B 110.3 . . ?
N1 C24 C23 107.3(6) . . ?
H24A C24 H24B 108.5 . . ?
C23 C24 H24A 110.3 . . ?
C23 C24 H24B 110.3 . . ?
C18 C17 C16 120.2(5) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
O2 C22 C21 100.3(10) . . ?
O2 C22 H22A 111.7 . . ?
O2 C22 H22B 111.7 . . ?
C21 C22 H22A 111.7 . . ?
C21 C22 H22B 111.7 . . ?
H22A C22 H22B 109.5 . . ?
O2 C23 C24 103.4(8) . . ?
O2 C23 H23A 111.1 . . ?
O2 C23 H23B 111.1 . . ?
C24 C23 H23A 111.1 . . ?
C24 C23 H23B 111.1 . . ?
H23A C23 H23B 109.0 . . ?
C22A O2A C23A 95(2) . . ?
O2A C23A H23C 112.6 . . ?
O2A C23A H23D 112.6 . . ?
O2A C23A C24A 96(2) . . ?
H23C C23A H23D 110.1 . . ?
C24A C23A H23C 112.6 . . ?
C24A C23A H23D 112.6 . . ?
O2A C22A H22C 108.3 . . ?
O2A C22A H22D 108.3 . . ?
O2A C22A C21A 116(2) . . ?
H22C C22A H22D 107.4 . . ?
C21A C22A H22C 108.3 . . ?
C21A C22A H22D 108.3 . . ?
N1 C24A C23A 104(3) . . ?
N1 C24A H24C 111.0 . . ?
N1 C24A H24D 111.0 . . ?
C23A C24A H24C 111.0 . . ?
C23A C24A H24D 111.0 . . ?
H24C C24A H24D 109.0 . . ?
N1 C21A H21C 111.1 . . ?
N1 C21A H21D 111.1 . . ?
C22A C21A N1 103.2(18) . . ?
C22A C21A H21C 111.1 . . ?
C22A C21A H21D 111.1 . . ?
H21C C21A H21D 109.1 . . ?

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 C5 C4 C3 -31.6(3) . . . . ?
S1 C5 C4 C13 93.3(3) . . . . ?
S1 C5 C19 O1 -10.8(5) . . . . ?
S1 C5 C19 C20 168.7(3) . . . . ?
N4 C6 C5 S1 -58.3(4) . . . . ?
N4 C6 C5 C4 -173.6(3) . . . . ?
N4 C6 C5 C19 61.9(4) . . . . ?
N4 C7 C12 C11 178.9(4) . . . . ?
N4 C7 C8 C9 -179.3(5) . . . . ?
O3 C6 C5 S1 121.6(4) . . . . ?
O3 C6 C5 C4 6.4(5) . . . . ?
O3 C6 C5 C19 -118.1(4) . . . . ?
N1 C21 C22 O2 71.0(13) . . . . ?
N1 C24 C23 O2 -67.3(10) . . . . ?
C6 N4 C7 C12 176.9(4) . . . . ?
C6 N4 C7 C8 -6.7(7) . . . . ?
C6 C5 C4 C3 85.1(3) . . . . ?
C6 C5 C4 C13 -150.0(3) . . . . ?
C6 C5 C19 O1 -130.1(4) . . . . ?
C6 C5 C19 C20 49.4(5) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C13 C18 C17 C16 0.6(11) . . . . ?
C5 S1 C2 N1 163.5(3) . . . . ?
C5 S1 C2 C3 -16.0(3) . . . . ?
C7 N4 C6 O3 -2.2(7) . . . . ?
C7 N4 C6 C5 177.7(3) . . . . ?
C7 C12 C11 C10 -0.6(8) . . . . ?
C7 C8 C9 C10 1.8(9) . . . . ?
C4 C3 C2 S1 -1.6(4) . . . . ?
C4 C3 C2 N1 178.9(4) . . . . ?
C4 C13 C14 C15 178.4(4) . . . . ?
C4 C13 C18 C17 -178.8(6) . . . . ?
C4 C5 C19 O1 106.8(4) . . . . ?
C4 C5 C19 C20 -73.7(4) . . . . ?
C14 C13 C4 C3 46.7(5) . . . . ?
C14 C13 C4 C5 -73.6(4) . . . . ?
C14 C13 C18 C17 0.6(8) . . . . ?
C14 C15 C16 C17 1.1(9) . . . . ?
C19 C5 C4 C3 -151.5(3) . . . . ?
C19 C5 C4 C13 -26.6(4) . . . . ?
C2 S1 C5 C6 -90.1(3) . . . . ?
C2 S1 C5 C4 27.7(2) . . . . ?
C2 S1 C5 C19 149.3(3) . . . . ?
C2 N1 C21 C22 148.1(8) . . . . ?
C2 N1 C24 C23 -149.0(6) . . . . ?
C2 N1 C24A C23A 154.5(18) . . . . ?
C2 N1 C21A C22A -172.6(13) . . . . ?
C2 C3 C4 C13 -103.6(4) . . . . ?
C2 C3 C4 C5 22.3(4) . . . . ?
C1 C3 C4 C13 69.7(4) . . . . ?
C1 C3 C4 C5 -164.5(3) . . . . ?
C1 C3 C2 S1 -173.9(3) . . . . ?
C1 C3 C2 N1 6.6(7) . . . . ?
C12 C7 C8 C9 -3.0(7) . . . . ?
C12 C11 C10 C9 -0.6(9) . . . . ?
C8 C7 C12 C11 2.4(7) . . . . ?
C15 C16 C17 C18 -1.4(11) . . . . ?
C11 C10 C9 C8 0.0(9) . . . . ?
C18 C13 C4 C3 -133.9(4) . . . . ?
C18 C13 C4 C5 105.7(5) . . . . ?
C18 C13 C14 C15 -0.9(6) . . . . ?
C21 N1 C2 S1 163.0(7) . . . . ?
C21 N1 C2 C3 -17.5(9) . . . . ?
C21 N1 C24 C23 60.3(10) . . . . ?
C24 N1 C2 S1 17.4(6) . . . . ?
C24 N1 C2 C3 -163.1(5) . . . . ?
C24 N1 C21 C22 -62.8(10) . . . . ?
C22 O2 C23 C24 77.1(11) . . . . ?
C23 O2 C22 C21 -76.6(13) . . . . ?
O2A C23A C24A N1 77(3) . . . . ?
O2A C22A C21A N1 -46(3) . . . . ?
C23A O2A C22A C21A 78(3) . . . . ?
C22A O2A C23A C24A -88(3) . . . . ?
C24A N1 C2 S1 -22.3(16) . . . . ?
C24A N1 C2 C3 157.2(15) . . . . ?
C24A N1 C21A C22A 32(3) . . . . ?
C21A N1 C2 S1 -177.5(13) . . . . ?
C21A N1 C2 C3 2.0(14) . . . . ?
C21A N1 C24A C23A -52(3) . . . . ?


_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
;
####################################################################### 
# 
# 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_psu-1419(g-2)
_database_code_depnum_ccdc_archive 'CCDC 2288496'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-14
_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         'C20 H22 N2 O2 S'
_chemical_formula_sum            'C20 H22 N2 O2 S'
_chemical_formula_weight         354.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O 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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1006(15)
_cell_length_b                   15.187(3)
_cell_length_c                   25.844(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3572.0(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2861
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.4510
_cell_measurement_theta_min      2.4510
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.467
_diffrn_reflns_theta_min         2.682
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   90.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       14.0072   57.0000  -60.0000 105

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00  -61.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -44.0000   39.3507 28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0068634000
_diffrn_orient_matrix_UB_12      0.0370947000
_diffrn_orient_matrix_UB_13      -0.0163150000
_diffrn_orient_matrix_UB_21      -0.0063160000
_diffrn_orient_matrix_UB_22      0.0276063000
_diffrn_orient_matrix_UB_23      0.0220689000
_diffrn_orient_matrix_UB_31      0.0775619000
_diffrn_orient_matrix_UB_32      0.0057013000
_diffrn_orient_matrix_UB_33      0.0005301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3113
_reflns_number_total             4247
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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         0.302
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0081(6)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.038
_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)+(0.0458P)²+1.2252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1245
_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 Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
;
_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 0.37197(5) 0.16522(3) 0.60113(2) 0.04324(17) Uani 1 1 d . . . . .
N1 N 0.0248(2) 0.42308(11) 0.63692(7) 0.0511(5) Uani 1 1 d . . . . .
O1 O 0.62089(17) 0.35335(11) 0.72465(6) 0.0650(5) Uani 1 1 d . . . . .
C1 C 0.31521(19) 0.26950(12) 0.62342(7) 0.0341(4) Uani 1 1 d . . . . .
O2 O 0.16905(19) 0.25302(10) 0.49692(6) 0.0588(4) Uani 1 1 d . . . . .
N2 N 0.41732(18) 0.32209(13) 0.64536(7) 0.0524(5) Uani 1 1 d . . . . .
C2 C 0.16744(18) 0.28225(11) 0.61739(7) 0.0297(4) Uani 1 1 d . . . . .
C3 C 0.08171(18) 0.20549(11) 0.59547(7) 0.0303(4) Uani 1 1 d . . . . .
H3 H 0.012992 0.229150 0.569803 0.036 Uiso 1 1 calc R U . . .
C4 C 0.19692(18) 0.14920(11) 0.56596(7) 0.0302(4) Uani 1 1 d . . . . .
C5 C 0.22675(19) 0.18588(12) 0.51169(7) 0.0347(4) Uani 1 1 d . . . . .
C6 C 0.3278(2) 0.13316(13) 0.47759(8) 0.0406(5) Uani 1 1 d . . . . .
H6A H 0.427340 0.137021 0.490795 0.049 Uiso 1 1 calc R U . . .
H6B H 0.326916 0.157600 0.442914 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2811(2) 0.03756(13) 0.47555(8) 0.0456(5) Uani 1 1 d . . . . .
H7A H 0.187000 0.032972 0.458099 0.055 Uiso 1 1 calc R U . . .
H7B H 0.352496 0.004067 0.455842 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2684(2) -0.00064(13) 0.52929(8) 0.0475(5) Uani 1 1 d . . . . .
H8A H 0.364203 -0.000101 0.545730 0.057 Uiso 1 1 calc R U . . .
H8B H 0.235991 -0.061357 0.526949 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1603(2) 0.05130(11) 0.56232(8) 0.0398(5) Uani 1 1 d . . . . .
H9A H 0.158968 0.026526 0.596911 0.048 Uiso 1 1 calc R U . . .
H9B H 0.062522 0.044768 0.547854 0.048 Uiso 1 1 calc R U . . .
C10 C -0.00816(18) 0.15696(11) 0.63589(7) 0.0326(4) Uani 1 1 d . . . . .
C11 C 0.0394(2) 0.14744(12) 0.68669(8) 0.0396(5) Uani 1 1 d . . . . .
H11 H 0.128834 0.171530 0.696797 0.048 Uiso 1 1 calc R U . . .
C12 C -0.0455(2) 0.10236(13) 0.72232(9) 0.0495(5) Uani 1 1 d . . . . .
H12 H -0.012914 0.096763 0.756265 0.059 Uiso 1 1 calc R U . . .
C13 C -0.1778(3) 0.06571(13) 0.70804(10) 0.0543(6) Uani 1 1 d . . . . .
H13 H -0.233611 0.034956 0.732160 0.065 Uiso 1 1 calc R U . . .
C14 C -0.2273(2) 0.07465(13) 0.65799(11) 0.0546(6) Uani 1 1 d . . . . .
H14 H -0.316415 0.049827 0.648165 0.065 Uiso 1 1 calc R U . . .
C15 C -0.1437(2) 0.12080(13) 0.62226(9) 0.0442(5) Uani 1 1 d . . . . .
H15 H -0.178500 0.127769 0.588679 0.053 Uiso 1 1 calc R U . . .
C16 C 0.0917(2) 0.36089(12) 0.62893(7) 0.0334(4) Uani 1 1 d . . . . .
C17 C 0.3836(2) 0.38374(13) 0.68674(8) 0.0429(5) Uani 1 1 d . . . . .
H17A H 0.279084 0.382630 0.694034 0.052 Uiso 1 1 calc R U . . .
H17B H 0.409963 0.442975 0.676205 0.052 Uiso 1 1 calc R U . . .
C18 C 0.4671(3) 0.35902(15) 0.73379(8) 0.0509(5) Uani 1 1 d . . . . .
H18A H 0.448943 0.402379 0.760600 0.061 Uiso 1 1 calc R U . . .
H18B H 0.431828 0.302595 0.746259 0.061 Uiso 1 1 calc R U . . .
C19 C 0.6519(3) 0.29078(17) 0.68564(10) 0.0622(7) Uani 1 1 d . . . . .
H19A H 0.620854 0.232907 0.697137 0.075 Uiso 1 1 calc R U . . .
H19B H 0.757086 0.288839 0.679602 0.075 Uiso 1 1 calc R U . . .
C20 C 0.5755(2) 0.31321(16) 0.63671(8) 0.0500(6) Uani 1 1 d . . . . .
H20A H 0.614299 0.368051 0.623163 0.060 Uiso 1 1 calc R U . . .
H20B H 0.593334 0.267423 0.611301 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7627(19) . ?
S1 C4 1.8502(18) . ?
N1 C16 1.142(2) . ?
O1 C18 1.422(3) . ?
O1 C19 1.414(3) . ?
C1 N2 1.350(2) . ?
C1 C2 1.368(2) . ?
O2 C5 1.209(2) . ?
N2 C17 1.454(2) . ?
N2 C20 1.463(3) . ?
C2 C3 1.513(2) . ?
C2 C16 1.411(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.553(2) . ?
C3 C10 1.518(2) . ?
C4 C5 1.533(3) . ?
C4 C9 1.527(2) . ?
C5 C6 1.504(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.514(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.510(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.523(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.390(3) . ?
C10 C15 1.395(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.482(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.483(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 91.52(8) . . ?
C19 O1 C18 110.85(17) . . ?
N2 C1 S1 117.84(14) . . ?
N2 C1 C2 129.87(17) . . ?
C2 C1 S1 112.21(13) . . ?
C1 N2 C17 122.99(16) . . ?
C1 N2 C20 123.96(16) . . ?
C17 N2 C20 112.29(15) . . ?
C1 C2 C3 116.15(15) . . ?
C1 C2 C16 125.20(16) . . ?
C16 C2 C3 118.64(15) . . ?
C2 C3 H3 107.5 . . ?
C2 C3 C4 105.07(13) . . ?
C2 C3 C10 113.24(14) . . ?
C4 C3 H3 107.5 . . ?
C10 C3 H3 107.5 . . ?
C10 C3 C4 115.75(14) . . ?
C3 C4 S1 105.52(11) . . ?
C5 C4 S1 104.42(12) . . ?
C5 C4 C3 111.64(14) . . ?
C9 C4 S1 110.27(12) . . ?
C9 C4 C3 114.77(14) . . ?
C9 C4 C5 109.64(14) . . ?
O2 C5 C4 121.22(17) . . ?
O2 C5 C6 121.98(18) . . ?
C6 C5 C4 116.79(16) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.05(15) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 110.98(16) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.47(17) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C4 C9 H9A 108.9 . . ?
C4 C9 H9B 108.9 . . ?
C8 C9 C4 113.44(16) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C3 122.20(16) . . ?
C11 C10 C15 118.21(18) . . ?
C15 C10 C3 119.59(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.43(19) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
N1 C16 C2 176.7(2) . . ?
N2 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
N2 C17 C18 109.41(17) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
O1 C18 C17 112.54(18) . . ?
O1 C18 H18A 109.1 . . ?
O1 C18 H18B 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
O1 C19 H19A 109.4 . . ?
O1 C19 H19B 109.4 . . ?
O1 C19 C20 111.10(19) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
N2 C20 C19 110.63(18) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?

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 C1 N2 C17 -147.64(17) . . . . ?
S1 C1 N2 C20 21.6(3) . . . . ?
S1 C1 C2 C3 2.4(2) . . . . ?
S1 C1 C2 C16 -176.24(15) . . . . ?
S1 C4 C5 O2 -110.42(18) . . . . ?
S1 C4 C5 C6 71.05(16) . . . . ?
S1 C4 C9 C8 -65.95(19) . . . . ?
O1 C19 C20 N2 -55.5(3) . . . . ?
C1 S1 C4 C3 -26.75(12) . . . . ?
C1 S1 C4 C5 91.06(12) . . . . ?
C1 S1 C4 C9 -151.23(13) . . . . ?
C1 N2 C17 C18 117.6(2) . . . . ?
C1 N2 C20 C19 -116.7(2) . . . . ?
C1 C2 C3 C4 -22.6(2) . . . . ?
C1 C2 C3 C10 104.66(18) . . . . ?
O2 C5 C6 C7 -127.9(2) . . . . ?
N2 C1 C2 C3 -174.27(19) . . . . ?
N2 C1 C2 C16 7.1(3) . . . . ?
N2 C17 C18 O1 55.3(2) . . . . ?
C2 C1 N2 C17 28.9(3) . . . . ?
C2 C1 N2 C20 -161.9(2) . . . . ?
C2 C3 C4 S1 30.84(15) . . . . ?
C2 C3 C4 C5 -82.01(16) . . . . ?
C2 C3 C4 C9 152.44(15) . . . . ?
C2 C3 C10 C11 -34.0(2) . . . . ?
C2 C3 C10 C15 145.55(16) . . . . ?
C3 C4 C5 O2 3.1(2) . . . . ?
C3 C4 C5 C6 -175.42(14) . . . . ?
C3 C4 C9 C8 175.07(16) . . . . ?
C3 C10 C11 C12 -179.70(16) . . . . ?
C3 C10 C15 C14 178.78(17) . . . . ?
C4 S1 C1 N2 -167.92(16) . . . . ?
C4 S1 C1 C2 14.95(15) . . . . ?
C4 C3 C10 C11 87.4(2) . . . . ?
C4 C3 C10 C15 -93.04(19) . . . . ?
C4 C5 C6 C7 50.7(2) . . . . ?
C5 C4 C9 C8 48.5(2) . . . . ?
C5 C6 C7 C8 -54.2(2) . . . . ?
C6 C7 C8 C9 57.6(2) . . . . ?
C7 C8 C9 C4 -55.8(2) . . . . ?
C9 C4 C5 O2 131.44(19) . . . . ?
C9 C4 C5 C6 -47.1(2) . . . . ?
C10 C3 C4 S1 -94.86(15) . . . . ?
C10 C3 C4 C5 152.29(15) . . . . ?
C10 C3 C4 C9 26.7(2) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C10 C15 C14 -1.6(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 1.4(3) . . . . ?
C15 C10 C11 C12 0.7(3) . . . . ?
C16 C2 C3 C4 156.16(16) . . . . ?
C16 C2 C3 C10 -76.6(2) . . . . ?
C17 N2 C20 C19 53.6(3) . . . . ?
C18 O1 C19 C20 58.0(3) . . . . ?
C19 O1 C18 C17 -58.7(2) . . . . ?
C20 N2 C17 C18 -52.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1281
_database_code_depnum_ccdc_archive 'CCDC 2306789'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2023-11-09
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H27 N3 O3 S'
_chemical_formula_sum            'C23 H27 N3 O3 S'
_chemical_formula_weight         425.54
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   18.9394(6)
_cell_length_b                   9.8877(3)
_cell_length_c                   11.9483(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.354(3)
_cell_angle_gamma                90.00
_cell_volume                     2135.67(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3775
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.1850
_cell_measurement_theta_min      2.4780
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10192
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.14
_diffrn_reflns_theta_min         2.35
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9891
_diffrn_measured_fraction_theta_max 0.8461
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  -2.00   1.00   10.00    --  -19.22 -77.00-150.00   36
  2  ω    -85.00  -3.00   1.00   10.00    --  -19.22 -57.00  60.00   82
  3  ω    -40.00  44.00   1.00   10.00    --   21.72 -19.00 150.00   84
;
_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      -0.0097488000
_diffrn_orient_matrix_UB_12      -0.0673087000
_diffrn_orient_matrix_UB_13      0.0097409000
_diffrn_orient_matrix_UB_21      -0.0282106000
_diffrn_orient_matrix_UB_22      0.0008686000
_diffrn_orient_matrix_UB_23      -0.0545717000
_diffrn_orient_matrix_UB_31      0.0254358000
_diffrn_orient_matrix_UB_32      -0.0248482000
_diffrn_orient_matrix_UB_33      -0.0282235000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4004
_reflns_number_total             5831
_reflns_odcompleteness_completeness 98.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         5831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.2217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1397
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.28118(3) 0.41669(5) 0.50318(4) 0.04834(16) Uani 1 1 d . . .
N2 N 0.31400(8) 0.71389(16) 0.62252(13) 0.0401(3) Uani 1 1 d . . .
O2 O 0.29102(7) 0.74550(15) 0.42615(11) 0.0511(4) Uani 1 1 d . . .
O3 O 0.19511(8) 0.59591(16) 0.66566(11) 0.0567(4) Uani 1 1 d . . .
O4 O 0.00019(8) 0.84621(16) 0.26066(12) 0.0662(5) Uani 1 1 d . . .
N1 N 0.11951(7) 0.65978(14) 0.32671(11) 0.0324(3) Uani 1 1 d . . .
C1 C 0.27893(8) 0.68874(18) 0.50837(14) 0.0347(4) Uani 1 1 d . . .
C1A C 0.49595(12) 0.9615(3) 0.7789(2) 0.0668(7) Uani 1 1 d . . .
H1A H 0.5363 1.0161 0.8151 0.080 Uiso 1 1 calc R . .
C1B C 0.46199(12) 0.9711(2) 0.6610(2) 0.0639(6) Uani 1 1 d . . .
H1B H 0.4797 1.0327 0.6170 0.077 Uiso 1 1 calc R . .
C2 C 0.22375(8) 0.56883(16) 0.48448(13) 0.0314(3) Uani 1 1 d . . .
C3 C 0.17593(9) 0.56853(16) 0.35676(13) 0.0308(3) Uani 1 1 d . . .
C4 C 0.19231(9) 0.46760(17) 0.29108(13) 0.0352(4) Uani 1 1 d . . .
C5 C 0.25081(9) 0.36455(17) 0.34882(13) 0.0328(3) Uani 1 1 d . . .
N3 N 0.13878(12) 0.4204(2) 0.07114(15) 0.0811(7) Uani 1 1 d . . .
C7 C -0.00644(10) 0.7145(2) 0.21178(17) 0.0510(5) Uani 1 1 d . . .
H7A H -0.0398 0.7171 0.1325 0.061 Uiso 1 1 calc R . .
H7B H -0.0276 0.6546 0.2575 0.061 Uiso 1 1 calc R . .
C8 C 0.31601(10) 0.3688(2) 0.29746(17) 0.0433(4) Uani 1 1 d . . .
H8A H 0.2978 0.3526 0.2137 0.052 Uiso 1 1 calc R . .
H8B H 0.3380 0.4583 0.3093 0.052 Uiso 1 1 calc R . .
C9 C 0.27960(10) 0.11736(19) 0.39815(17) 0.0444(4) Uani 1 1 d . . .
H9A H 0.2982 0.1354 0.4816 0.053 Uiso 1 1 calc R . .
H9B H 0.2582 0.0274 0.3877 0.053 Uiso 1 1 calc R . .
C10 C 0.22019(9) 0.22080(18) 0.34062(15) 0.0402(4) Uani 1 1 d . . .
H10A H 0.1814 0.2175 0.3783 0.048 Uiso 1 1 calc R . .
H10B H 0.1984 0.1972 0.2587 0.048 Uiso 1 1 calc R . .
C11 C 0.37547(9) 0.79911(18) 0.67052(14) 0.0365(4) Uani 1 1 d . . .
C12 C 0.37498(10) 0.2645(2) 0.35318(19) 0.0513(5) Uani 1 1 d . . .
H12A H 0.4131 0.2667 0.3141 0.062 Uiso 1 1 calc R . .
H12B H 0.3978 0.2876 0.4349 0.062 Uiso 1 1 calc R . .
C13 C 0.34307(11) 0.1230(2) 0.34514(17) 0.0488(5) Uani 1 1 d . . .
H13A H 0.3815 0.0604 0.3862 0.059 Uiso 1 1 calc R . .
H13B H 0.3256 0.0955 0.2636 0.059 Uiso 1 1 calc R . .
C14 C 0.40210(11) 0.8913(2) 0.60585(18) 0.0513(5) Uani 1 1 d . . .
H14 H 0.3797 0.8994 0.5255 0.062 Uiso 1 1 calc R . .
C15 C 0.46963(11) 0.8703(3) 0.8430(2) 0.0627(6) Uani 1 1 d . . .
H15 H 0.4921 0.8634 0.9234 0.075 Uiso 1 1 calc R . .
C16 C 0.41002(10) 0.7887(2) 0.78948(16) 0.0485(5) Uani 1 1 d . . .
H16 H 0.3931 0.7263 0.8338 0.058 Uiso 1 1 calc R . .
C17 C 0.12311(9) 0.79191(18) 0.38427(15) 0.0399(4) Uani 1 1 d . . .
H17A H 0.1462 0.8573 0.3458 0.048 Uiso 1 1 calc R . .
H17B H 0.1531 0.7848 0.4655 0.048 Uiso 1 1 calc R . .
C18 C 0.04655(11) 0.8391(2) 0.37853(18) 0.0583(6) Uani 1 1 d . . .
H18A H 0.0251 0.7771 0.4223 0.070 Uiso 1 1 calc R . .
H18B H 0.0495 0.9276 0.4146 0.070 Uiso 1 1 calc R . .
C19 C 0.16037(11) 0.4472(2) 0.16846(16) 0.0492(5) Uani 1 1 d . . .
C20 C 0.06677(9) 0.65956(18) 0.20949(14) 0.0376(4) Uani 1 1 d . . .
H20A H 0.0604 0.5679 0.1791 0.045 Uiso 1 1 calc R . .
H20B H 0.0859 0.7142 0.1576 0.045 Uiso 1 1 calc R . .
C21 C 0.17708(9) 0.54761(18) 0.56918(14) 0.0373(4) Uani 1 1 d . . .
C22 C 0.11102(11) 0.4570(2) 0.53078(17) 0.0563(5) Uani 1 1 d . . .
H22A H 0.1269 0.3644 0.5367 0.084 Uiso 1 1 calc R . .
H22B H 0.0838 0.4770 0.4509 0.084 Uiso 1 1 calc R . .
H22C H 0.0799 0.4714 0.5801 0.084 Uiso 1 1 calc R . .
H2 H 0.2944(11) 0.674(2) 0.6724(19) 0.058(6) 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 C2 1.8306(16) . ?
S1 C5 1.8345(16) . ?
N2 C1 1.350(2) . ?
N2 C11 1.413(2) . ?
N2 H2 0.88(2) . ?
O2 C1 1.211(2) . ?
O3 C21 1.199(2) . ?
O4 C7 1.418(2) . ?
O4 C18 1.422(2) . ?
N1 C3 1.362(2) . ?
N1 C17 1.468(2) . ?
N1 C20 1.4577(19) . ?
C1 C2 1.550(2) . ?
C1A H1A 0.9300 . ?
C1A C1B 1.367(3) . ?
C1A C15 1.369(3) . ?
C1B H1B 0.9300 . ?
C1B C14 1.377(3) . ?
C2 C3 1.525(2) . ?
C2 C21 1.544(2) . ?
C3 C4 1.361(2) . ?
C4 C5 1.512(2) . ?
C4 C19 1.423(2) . ?
C5 C8 1.535(2) . ?
C5 C10 1.527(2) . ?
N3 C19 1.143(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C20 1.497(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C12 1.520(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.524(2) . ?
C9 C13 1.518(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C14 1.384(3) . ?
C11 C16 1.380(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.516(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.380(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.505(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.495(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C2 S1 C5 96.40(7) . . ?
C1 N2 C11 128.13(16) . . ?
C1 N2 H2 115.0(14) . . ?
C11 N2 H2 116.8(14) . . ?
C7 O4 C18 108.36(15) . . ?
C3 N1 C17 122.86(13) . . ?
C3 N1 C20 120.74(13) . . ?
C20 N1 C17 111.97(13) . . ?
N2 C1 C2 115.37(14) . . ?
O2 C1 N2 125.38(17) . . ?
O2 C1 C2 119.04(14) . . ?
C1B C1A H1A 120.5 . . ?
C1B C1A C15 119.0(2) . . ?
C15 C1A H1A 120.5 . . ?
C1A C1B H1B 119.3 . . ?
C1A C1B C14 121.4(2) . . ?
C14 C1B H1B 119.3 . . ?
C1 C2 S1 105.23(10) . . ?
C3 C2 S1 105.93(10) . . ?
C3 C2 C1 110.64(13) . . ?
C3 C2 C21 111.75(13) . . ?
C21 C2 S1 104.12(11) . . ?
C21 C2 C1 118.02(13) . . ?
N1 C3 C2 116.59(13) . . ?
C4 C3 N1 128.99(14) . . ?
C4 C3 C2 114.14(14) . . ?
C3 C4 C5 119.54(14) . . ?
C3 C4 C19 126.70(15) . . ?
C19 C4 C5 113.75(14) . . ?
C4 C5 S1 103.69(11) . . ?
C4 C5 C8 111.50(14) . . ?
C4 C5 C10 112.66(13) . . ?
C8 C5 S1 110.24(11) . . ?
C10 C5 S1 108.98(11) . . ?
C10 C5 C8 109.61(14) . . ?
O4 C7 H7A 109.2 . . ?
O4 C7 H7B 109.2 . . ?
O4 C7 C20 111.86(16) . . ?
H7A C7 H7B 107.9 . . ?
C20 C7 H7A 109.2 . . ?
C20 C7 H7B 109.2 . . ?
C5 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C12 C8 C5 112.32(15) . . ?
C12 C8 H8A 109.1 . . ?
C12 C8 H8B 109.1 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C13 C9 H9A 109.5 . . ?
C13 C9 H9B 109.5 . . ?
C13 C9 C10 110.93(15) . . ?
C5 C10 H10A 109.1 . . ?
C5 C10 H10B 109.1 . . ?
C9 C10 C5 112.35(14) . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C14 C11 N2 124.04(16) . . ?
C16 C11 N2 116.98(16) . . ?
C16 C11 C14 118.98(17) . . ?
C8 C12 H12A 109.3 . . ?
C8 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 C8 111.81(16) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C9 C13 H13A 109.4 . . ?
C9 C13 H13B 109.4 . . ?
C12 C13 C9 110.97(16) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C1B C14 C11 119.71(19) . . ?
C1B C14 H14 120.1 . . ?
C11 C14 H14 120.1 . . ?
C1A C15 H15 119.7 . . ?
C1A C15 C16 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.3(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N1 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
N1 C17 C18 110.17(15) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
O4 C18 C17 111.26(16) . . ?
O4 C18 H18A 109.4 . . ?
O4 C18 H18B 109.4 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N3 C19 C4 173.7(2) . . ?
N1 C20 C7 110.79(14) . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
C7 C20 H20A 109.5 . . ?
C7 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
O3 C21 C2 121.43(16) . . ?
O3 C21 C22 120.38(16) . . ?
C22 C21 C2 118.06(15) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C2 C3 N1 169.10(12) . . . . ?
S1 C2 C3 C4 -5.41(18) . . . . ?
S1 C2 C21 O3 96.54(18) . . . . ?
S1 C2 C21 C22 -79.41(17) . . . . ?
S1 C5 C8 C12 66.21(18) . . . . ?
S1 C5 C10 C9 -65.95(16) . . . . ?
N2 C1 C2 S1 -78.09(15) . . . . ?
N2 C1 C2 C3 167.92(14) . . . . ?
N2 C1 C2 C21 37.5(2) . . . . ?
N2 C11 C14 C1B 179.30(18) . . . . ?
N2 C11 C16 C15 -178.85(18) . . . . ?
O2 C1 C2 S1 97.01(16) . . . . ?
O2 C1 C2 C3 -17.0(2) . . . . ?
O2 C1 C2 C21 -147.44(16) . . . . ?
O4 C7 C20 N1 56.4(2) . . . . ?
N1 C3 C4 C5 -170.48(16) . . . . ?
N1 C3 C4 C19 10.5(3) . . . . ?
N1 C17 C18 O4 -57.2(2) . . . . ?
C1 N2 C11 C14 12.3(3) . . . . ?
C1 N2 C11 C16 -168.07(17) . . . . ?
C1 C2 C3 N1 -77.36(17) . . . . ?
C1 C2 C3 C4 108.13(16) . . . . ?
C1 C2 C21 O3 -19.6(2) . . . . ?
C1 C2 C21 C22 164.45(16) . . . . ?
C1A C1B C14 C11 -0.1(4) . . . . ?
C1A C15 C16 C11 -0.8(3) . . . . ?
C1B C1A C15 C16 0.4(4) . . . . ?
C2 S1 C5 C4 -3.40(12) . . . . ?
C2 S1 C5 C8 116.06(12) . . . . ?
C2 S1 C5 C10 -123.61(12) . . . . ?
C2 C3 C4 C5 3.2(2) . . . . ?
C2 C3 C4 C19 -175.78(18) . . . . ?
C3 N1 C17 C18 -152.49(16) . . . . ?
C3 N1 C20 C7 152.38(16) . . . . ?
C3 C2 C21 O3 -149.56(17) . . . . ?
C3 C2 C21 C22 34.5(2) . . . . ?
C3 C4 C5 S1 0.72(19) . . . . ?
C3 C4 C5 C8 -117.87(18) . . . . ?
C3 C4 C5 C10 118.39(18) . . . . ?
C3 C4 C19 N3 -179(100) . . . . ?
C4 C5 C8 C12 -179.19(16) . . . . ?
C4 C5 C10 C9 179.54(14) . . . . ?
C5 S1 C2 C1 -112.24(11) . . . . ?
C5 S1 C2 C3 5.00(12) . . . . ?
C5 S1 C2 C21 122.98(11) . . . . ?
C5 C4 C19 N3 2(2) . . . . ?
C5 C8 C12 C13 54.9(2) . . . . ?
C7 O4 C18 C17 62.1(2) . . . . ?
C8 C5 C10 C9 54.77(19) . . . . ?
C8 C12 C13 C9 -55.2(2) . . . . ?
C10 C5 C8 C12 -53.7(2) . . . . ?
C10 C9 C13 C12 55.7(2) . . . . ?
C11 N2 C1 O2 -6.7(3) . . . . ?
C11 N2 C1 C2 168.05(15) . . . . ?
C13 C9 C10 C5 -56.5(2) . . . . ?
C14 C11 C16 C15 0.8(3) . . . . ?
C15 C1A C1B C14 0.1(4) . . . . ?
C16 C11 C14 C1B -0.3(3) . . . . ?
C17 N1 C3 C2 31.0(2) . . . . ?
C17 N1 C3 C4 -155.49(17) . . . . ?
C17 N1 C20 C7 -50.6(2) . . . . ?
C18 O4 C7 C20 -61.6(2) . . . . ?
C19 C4 C5 S1 179.83(14) . . . . ?
C19 C4 C5 C8 61.2(2) . . . . ?
C19 C4 C5 C10 -62.5(2) . . . . ?
C20 N1 C3 C2 -174.57(14) . . . . ?
C20 N1 C3 C4 -1.0(3) . . . . ?
C20 N1 C17 C18 51.1(2) . . . . ?
C21 C2 C3 N1 56.33(19) . . . . ?
C21 C2 C3 C4 -118.18(16) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.349
_oxdiff_exptl_absorpt_empirical_full_min 0.839
####################################################################### 
# 
# 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_210
_database_code_depnum_ccdc_archive 'CCDC 2288492'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-11-03
_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         'C17 H16 N4 O2 S'
_chemical_formula_sum            'C17 H16 N4 O2 S'
_chemical_formula_weight         340.40
_chemical_absolute_configuration ?
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   20.677(2)
_cell_length_b                   10.7808(7)
_cell_length_c                   15.1131(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3369.0(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2194
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.2890
_cell_measurement_theta_min      3.8100
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52686
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.1152
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11968
_diffrn_reflns_point_group_measured_fraction_full 0.752
_diffrn_reflns_point_group_measured_fraction_max 0.655
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.481
_diffrn_reflns_theta_min         3.759
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.894
_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  88.00   1.00   60.00    --   21.29  64.00 -33.00   54
  2  ω    -79.00 -50.00   1.00   60.00    --  -22.70-176.00 -24.00   29
  3  ω    -16.00  62.00   1.00   60.00    --   21.29 -99.00-180.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.416
_reflns_Friedel_fraction_full    0.491
_reflns_Friedel_fraction_max     0.398
_reflns_number_gt                3197
_reflns_number_total             6726
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.291
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.40(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6726
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.001
_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)+(0.0499P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1816
_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:
 C11(H11C,H11D), C9A(H9AA,H9AB), C11A(H11A,H11B), C8A(H8AA,H8AB), C9(H9A,H9B),
 C10(H10C,H10D), C8(H8A,H8B), C10A(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C14A(H14A), C18A(H18A), C14(H14), C17(H17), C15A(H15A), C16A(H16A),
 C17A(H17A), C15(H15), C16(H16)
;
_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
S1A S 0.41868(10) 0.66882(14) 0.71160(15) 0.0545(5) Uani 1 1 d . . . . .
S1 S 0.30926(10) 0.28137(15) 0.27715(15) 0.0552(5) Uani 1 1 d . . . . .
O1A O 0.3763(2) 0.9979(4) 0.6127(4) 0.0596(15) Uani 1 1 d . . . . .
O1 O 0.3544(3) -0.0516(4) 0.3685(4) 0.0678(17) Uani 1 1 d . . . . .
O2A O 0.4741(3) 0.2010(4) 0.7227(5) 0.083(2) Uani 1 1 d . . . . .
N1A N 0.4456(3) 0.4385(5) 0.6581(5) 0.0532(17) Uani 1 1 d . . . . .
N2A N 0.4484(4) 0.4987(6) 0.3954(5) 0.068(2) Uani 1 1 d . . . . .
N1 N 0.2871(3) 0.5106(5) 0.3359(5) 0.0520(16) Uani 1 1 d . . . . .
O2 O 0.2456(3) 0.7436(4) 0.2736(5) 0.0772(18) Uani 1 1 d . . . . .
N4A N 0.4456(3) 0.9416(6) 0.7213(6) 0.0591(19) Uani 1 1 d . . . . .
N2 N 0.2892(4) 0.4419(6) 0.5973(5) 0.0638(18) Uani 1 1 d . . . . .
N3A N 0.2730(3) 0.7490(6) 0.5923(5) 0.067(2) Uani 1 1 d . . . . .
C13A C 0.4987(3) 0.8151(5) 0.5343(5) 0.0439(17) Uani 1 1 d . . . . .
C13 C 0.2359(3) 0.1422(5) 0.4584(5) 0.0412(16) Uani 1 1 d . . . . .
C4A C 0.4345(3) 0.7467(5) 0.5414(6) 0.0400(16) Uani 1 1 d . . . . .
C7A C 0.4054(3) 0.9195(6) 0.6546(5) 0.0441(17) Uani 1 1 d . . . . .
C4 C 0.3022(3) 0.2002(5) 0.4461(5) 0.0408(16) Uani 1 1 d . . . . .
C6A C 0.3263(3) 0.7648(6) 0.6090(6) 0.0498(18) Uani 1 1 d . . . . .
C12 C 0.2931(3) 0.4010(6) 0.5271(5) 0.0452(16) Uani 1 1 d . . . . .
C2A C 0.4358(3) 0.5567(6) 0.6292(6) 0.0464(19) Uani 1 1 d . . . . .
C3A C 0.4386(3) 0.6066(6) 0.5463(6) 0.0451(17) Uani 1 1 d . . . . .
C18 C 0.2326(3) 0.0248(6) 0.4979(5) 0.0475(18) Uani 1 1 d . . . . .
H18 H 0.270206 -0.014471 0.516734 0.057 Uiso 1 1 calc R U . . .
C12A C 0.4446(3) 0.5430(6) 0.4641(6) 0.0494(19) Uani 1 1 d . . . . .
N4 N 0.2780(3) 0.0069(6) 0.2704(6) 0.0611(18) Uani 1 1 d . . . . .
C14A C 0.5536(3) 0.7813(6) 0.5836(6) 0.053(2) Uani 1 1 d . . . . .
H14A H 0.552331 0.711544 0.619806 0.064 Uiso 1 1 calc R U . . .
C18A C 0.5029(3) 0.9189(6) 0.4814(6) 0.0507(19) Uani 1 1 d . . . . .
H18A H 0.467171 0.942830 0.448134 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1786(3) 0.1979(6) 0.4321(6) 0.0510(19) Uani 1 1 d . . . . .
H14 H 0.179935 0.276166 0.406249 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2994(3) 0.3408(5) 0.4445(5) 0.0390(15) Uani 1 1 d . . . . .
C5A C 0.3959(3) 0.7818(5) 0.6271(5) 0.0406(16) Uani 1 1 d . . . . .
N3 N 0.4617(3) 0.1898(6) 0.3713(6) 0.067(2) Uani 1 1 d . . . . .
C5 C 0.3364(3) 0.1660(6) 0.3568(6) 0.0483(18) Uani 1 1 d . . . . .
C2 C 0.2987(3) 0.3929(6) 0.3622(5) 0.0426(16) Uani 1 1 d . . . . .
C17 C 0.1730(4) -0.0330(6) 0.5089(6) 0.060(2) Uani 1 1 d . . . . .
H17 H 0.170988 -0.110816 0.535316 0.072 Uiso 1 1 calc R U . . .
C15A C 0.6091(3) 0.8512(6) 0.5785(6) 0.058(2) Uani 1 1 d . . . . .
H15A H 0.645254 0.827281 0.610921 0.070 Uiso 1 1 calc R U . . .
C16A C 0.6123(3) 0.9548(6) 0.5268(7) 0.065(3) Uani 1 1 d . . . . .
H16A H 0.649776 1.002356 0.525259 0.078 Uiso 1 1 calc R U . . .
C17A C 0.5590(4) 0.9882(6) 0.4767(6) 0.058(2) Uani 1 1 d . . . . .
H17A H 0.560947 1.057196 0.439912 0.070 Uiso 1 1 calc R U . . .
C15 C 0.1201(3) 0.1405(7) 0.4432(6) 0.062(2) Uani 1 1 d . . . . .
H15 H 0.082371 0.179925 0.425130 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3235(4) 0.0291(6) 0.3312(6) 0.0478(18) Uani 1 1 d . . . . .
C16 C 0.1171(4) 0.0237(7) 0.4812(7) 0.068(2) Uani 1 1 d . . . . .
H16 H 0.077442 -0.015951 0.487845 0.082 Uiso 1 1 calc R U . . .
C6 C 0.4072(4) 0.1794(6) 0.3657(6) 0.0499(19) Uani 1 1 d . . . . .
C11 C 0.2746(5) 0.6116(6) 0.3951(6) 0.074(3) Uani 1 1 d . . . . .
H11C H 0.314773 0.654529 0.407492 0.089 Uiso 1 1 calc R U . . .
H11D H 0.258053 0.579117 0.450511 0.089 Uiso 1 1 calc R U . . .
C9A C 0.4655(6) 0.3008(7) 0.7823(8) 0.096(4) Uani 1 1 d . . . . .
H9AA H 0.507287 0.337168 0.795917 0.116 Uiso 1 1 calc R U . . .
H9AB H 0.446984 0.270084 0.837002 0.116 Uiso 1 1 calc R U . . .
C11A C 0.4607(4) 0.3370(6) 0.5990(7) 0.066(2) Uani 1 1 d . . . . .
H11A H 0.483349 0.369035 0.547634 0.080 Uiso 1 1 calc R U . . .
H11B H 0.420725 0.299392 0.578667 0.080 Uiso 1 1 calc R U . . .
C8A C 0.4226(5) 0.3973(7) 0.7444(6) 0.075(3) Uani 1 1 d . . . . .
H8AA H 0.379166 0.364206 0.738409 0.090 Uiso 1 1 calc R U . . .
H8AB H 0.420695 0.467684 0.784319 0.090 Uiso 1 1 calc R U . . .
C9 C 0.2547(6) 0.6454(7) 0.2149(8) 0.100(4) Uani 1 1 d . . . . .
H9A H 0.268827 0.678218 0.158407 0.121 Uiso 1 1 calc R U . . .
H9B H 0.213554 0.604043 0.205636 0.121 Uiso 1 1 calc R U . . .
C10 C 0.2278(6) 0.7000(8) 0.3586(8) 0.101(4) Uani 1 1 d . . . . .
H10C H 0.185793 0.660414 0.354898 0.121 Uiso 1 1 calc R U . . .
H10D H 0.224015 0.770101 0.398521 0.121 Uiso 1 1 calc R U . . .
C8 C 0.3026(7) 0.5533(8) 0.2463(7) 0.102(4) Uani 1 1 d . . . . .
H8A H 0.303088 0.482889 0.206313 0.123 Uiso 1 1 calc R U . . .
H8B H 0.345338 0.590291 0.246018 0.123 Uiso 1 1 calc R U . . .
C10A C 0.5008(5) 0.2420(7) 0.6421(8) 0.089(3) Uani 1 1 d . . . . .
H10A H 0.505528 0.171742 0.602518 0.107 Uiso 1 1 calc R U . . .
H10B H 0.543536 0.275818 0.653015 0.107 Uiso 1 1 calc R U . . .
H4 H 0.333(3) 0.155(4) 0.497(4) 0.025(14) Uiso 1 1 d . . . . .
H4A H 0.405(3) 0.784(4) 0.489(4) 0.026(15) Uiso 1 1 d . . . . .
H4AA H 0.479(4) 0.881(6) 0.756(6) 0.09(3) Uiso 1 1 d . . . . .
H4AB H 0.456(4) 1.025(7) 0.734(6) 0.08(3) Uiso 1 1 d . . . . .
H4B H 0.272(3) -0.081(5) 0.252(4) 0.038(17) Uiso 1 1 d . . . . .
H4C H 0.249(6) 0.076(9) 0.250(8) 0.14(4) 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
S1A C2A 1.772(7) . ?
S1A C5A 1.826(7) . ?
S1 C5 1.820(8) . ?
S1 C2 1.773(7) . ?
O1A C7A 1.215(8) . ?
O1 C7 1.219(8) . ?
O2A C9A 1.414(11) . ?
O2A C10A 1.410(12) . ?
N1A C2A 1.362(8) . ?
N1A C11A 1.446(9) . ?
N1A C8A 1.458(10) . ?
N2A C12A 1.146(10) . ?
N1 C2 1.351(8) . ?
N1 C11 1.433(9) . ?
N1 C8 1.466(11) . ?
O2 C9 1.394(11) . ?
O2 C10 1.416(13) . ?
N4A C7A 1.328(10) . ?
N4A H4AA 1.08(9) . ?
N4A H4AB 0.94(8) . ?
N2 C12 1.151(10) . ?
N3A C6A 1.143(9) . ?
C13A C4A 1.523(9) . ?
C13A C14A 1.406(10) . ?
C13A C18A 1.378(9) . ?
C13 C4 1.518(8) . ?
C13 C18 1.402(9) . ?
C13 C14 1.386(8) . ?
C4A C3A 1.515(8) . ?
C4A C5A 1.567(10) . ?
C4A H4A 1.07(6) . ?
C7A C5A 1.554(9) . ?
C4 C3 1.517(8) . ?
C4 C5 1.568(11) . ?
C4 H4 1.11(6) . ?
C6A C5A 1.476(9) . ?
C12 C3 1.413(10) . ?
C2A C3A 1.364(11) . ?
C3A C12A 1.425(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.391(10) . ?
N4 C7 1.337(10) . ?
N4 H4B 0.99(6) . ?
N4 H4C 1.01(11) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.375(9) . ?
C18A H18A 0.9300 . ?
C18A C17A 1.381(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(9) . ?
C3 C2 1.365(10) . ?
N3 C6 1.135(9) . ?
C5 C7 1.548(9) . ?
C5 C6 1.478(10) . ?
C17 H17 0.9300 . ?
C17 C16 1.374(11) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.365(10) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.385(11) . ?
C17A H17A 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.385(11) . ?
C16 H16 0.9300 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C11 C10 1.465(12) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C8A 1.484(12) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C11A C10A 1.471(12) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.481(14) . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?

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
C2A S1A C5A 90.9(3) . . ?
C2 S1 C5 91.2(4) . . ?
C10A O2A C9A 111.2(6) . . ?
C2A N1A C11A 122.8(7) . . ?
C2A N1A C8A 121.5(7) . . ?
C11A N1A C8A 113.1(6) . . ?
C2 N1 C11 124.2(7) . . ?
C2 N1 C8 121.9(7) . . ?
C11 N1 C8 112.2(6) . . ?
C9 O2 C10 111.1(6) . . ?
C7A N4A H4AA 131(4) . . ?
C7A N4A H4AB 118(5) . . ?
H4AA N4A H4AB 109(7) . . ?
C14A C13A C4A 122.7(6) . . ?
C18A C13A C4A 119.3(6) . . ?
C18A C13A C14A 117.9(6) . . ?
C18 C13 C4 117.9(5) . . ?
C14 C13 C4 123.9(6) . . ?
C14 C13 C18 118.2(6) . . ?
C13A C4A C5A 112.7(6) . . ?
C13A C4A H4A 105(3) . . ?
C3A C4A C13A 115.9(5) . . ?
C3A C4A C5A 103.2(5) . . ?
C3A C4A H4A 116(3) . . ?
C5A C4A H4A 103(3) . . ?
O1A C7A N4A 125.5(7) . . ?
O1A C7A C5A 117.6(7) . . ?
N4A C7A C5A 116.9(6) . . ?
C13 C4 C5 114.6(6) . . ?
C13 C4 H4 105(3) . . ?
C3 C4 C13 112.3(5) . . ?
C3 C4 C5 103.8(5) . . ?
C3 C4 H4 118(3) . . ?
C5 C4 H4 103(3) . . ?
N3A C6A C5A 177.5(9) . . ?
N2 C12 C3 174.9(8) . . ?
N1A C2A S1A 116.3(6) . . ?
N1A C2A C3A 131.1(7) . . ?
C3A C2A S1A 112.6(5) . . ?
C2A C3A C4A 115.9(6) . . ?
C2A C3A C12A 127.9(6) . . ?
C12A C3A C4A 116.2(7) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.9(6) . . ?
C17 C18 H18 120.1 . . ?
N2A C12A C3A 175.7(8) . . ?
C7 N4 H4B 117(3) . . ?
C7 N4 H4C 120(6) . . ?
H4B N4 H4C 123(7) . . ?
C13A C14A H14A 119.9 . . ?
C15A C14A C13A 120.1(7) . . ?
C15A C14A H14A 119.9 . . ?
C13A C18A H18A 119.3 . . ?
C13A C18A C17A 121.4(7) . . ?
C17A C18A H18A 119.3 . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.6(7) . . ?
C15 C14 H14 119.2 . . ?
C12 C3 C4 116.7(6) . . ?
C2 C3 C4 115.2(6) . . ?
C2 C3 C12 128.0(6) . . ?
C4A C5A S1A 106.6(4) . . ?
C7A C5A S1A 114.7(5) . . ?
C7A C5A C4A 112.8(5) . . ?
C6A C5A S1A 107.4(5) . . ?
C6A C5A C4A 108.2(6) . . ?
C6A C5A C7A 106.9(5) . . ?
C4 C5 S1 105.6(4) . . ?
C7 C5 S1 115.6(6) . . ?
C7 C5 C4 111.2(6) . . ?
C6 C5 S1 107.4(5) . . ?
C6 C5 C4 110.3(7) . . ?
C6 C5 C7 106.7(5) . . ?
N1 C2 S1 116.4(6) . . ?
N1 C2 C3 131.0(7) . . ?
C3 C2 S1 112.4(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.7(7) . . ?
C16 C17 H17 119.7 . . ?
C14A C15A H15A 119.3 . . ?
C16A C15A C14A 121.4(7) . . ?
C16A C15A H15A 119.3 . . ?
C15A C16A H16A 120.4 . . ?
C15A C16A C17A 119.2(7) . . ?
C17A C16A H16A 120.4 . . ?
C18A C17A C16A 120.0(7) . . ?
C18A C17A H17A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(7) . . ?
C16 C15 H15 119.9 . . ?
O1 C7 N4 124.0(7) . . ?
O1 C7 C5 118.3(7) . . ?
N4 C7 C5 117.7(7) . . ?
C17 C16 C15 119.5(7) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N3 C6 C5 179.1(10) . . ?
N1 C11 H11C 109.1 . . ?
N1 C11 H11D 109.1 . . ?
N1 C11 C10 112.3(8) . . ?
H11C C11 H11D 107.9 . . ?
C10 C11 H11C 109.1 . . ?
C10 C11 H11D 109.1 . . ?
O2A C9A H9AA 109.4 . . ?
O2A C9A H9AB 109.4 . . ?
O2A C9A C8A 111.3(8) . . ?
H9AA C9A H9AB 108.0 . . ?
C8A C9A H9AA 109.4 . . ?
C8A C9A H9AB 109.4 . . ?
N1A C11A H11A 109.2 . . ?
N1A C11A H11B 109.2 . . ?
N1A C11A C10A 112.0(8) . . ?
H11A C11A H11B 107.9 . . ?
C10A C11A H11A 109.2 . . ?
C10A C11A H11B 109.2 . . ?
N1A C8A C9A 111.3(9) . . ?
N1A C8A H8AA 109.4 . . ?
N1A C8A H8AB 109.4 . . ?
C9A C8A H8AA 109.4 . . ?
C9A C8A H8AB 109.4 . . ?
H8AA C8A H8AB 108.0 . . ?
O2 C9 H9A 108.9 . . ?
O2 C9 H9B 108.9 . . ?
O2 C9 C8 113.3(9) . . ?
H9A C9 H9B 107.7 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
O2 C10 C11 112.7(9) . . ?
O2 C10 H10C 109.1 . . ?
O2 C10 H10D 109.1 . . ?
C11 C10 H10C 109.1 . . ?
C11 C10 H10D 109.1 . . ?
H10C C10 H10D 107.8 . . ?
N1 C8 C9 111.1(9) . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O2A C10A C11A 112.3(8) . . ?
O2A C10A H10A 109.1 . . ?
O2A C10A H10B 109.1 . . ?
C11A C10A H10A 109.1 . . ?
C11A C10A H10B 109.1 . . ?
H10A C10A H10B 107.9 . . ?

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
S1A C2A C3A C4A 6.7(8) . . . . ?
S1A C2A C3A C12A -173.0(6) . . . . ?
S1 C5 C7 O1 161.1(6) . . . . ?
S1 C5 C7 N4 -20.0(9) . . . . ?
O1A C7A C5A S1A -161.2(6) . . . . ?
O1A C7A C5A C4A 76.6(8) . . . . ?
O1A C7A C5A C6A -42.2(9) . . . . ?
O2A C9A C8A N1A -54.0(11) . . . . ?
N1A C2A C3A C4A -171.1(6) . . . . ?
N1A C2A C3A C12A 9.3(13) . . . . ?
N1A C11A C10A O2A 52.4(10) . . . . ?
N1 C11 C10 O2 -53.6(12) . . . . ?
O2 C9 C8 N1 52.5(13) . . . . ?
N4A C7A C5A S1A 19.8(8) . . . . ?
N4A C7A C5A C4A -102.4(8) . . . . ?
N4A C7A C5A C6A 138.8(7) . . . . ?
C13A C4A C3A C2A 97.3(8) . . . . ?
C13A C4A C3A C12A -83.0(8) . . . . ?
C13A C4A C5A S1A -92.4(5) . . . . ?
C13A C4A C5A C7A 34.3(7) . . . . ?
C13A C4A C5A C6A 152.4(5) . . . . ?
C13A C14A C15A C16A 0.7(13) . . . . ?
C13A C18A C17A C16A -0.9(12) . . . . ?
C13 C4 C3 C12 78.0(8) . . . . ?
C13 C4 C3 C2 -97.5(7) . . . . ?
C13 C4 C5 S1 88.1(5) . . . . ?
C13 C4 C5 C7 -38.0(8) . . . . ?
C13 C4 C5 C6 -156.1(5) . . . . ?
C13 C18 C17 C16 0.2(13) . . . . ?
C13 C14 C15 C16 -0.2(14) . . . . ?
C4A C13A C14A C15A -176.0(7) . . . . ?
C4A C13A C18A C17A 176.3(7) . . . . ?
C4 C13 C18 C17 -178.7(7) . . . . ?
C4 C13 C14 C15 178.7(8) . . . . ?
C4 C3 C2 S1 -5.8(7) . . . . ?
C4 C3 C2 N1 169.1(7) . . . . ?
C4 C5 C7 O1 -78.5(8) . . . . ?
C4 C5 C7 N4 100.4(8) . . . . ?
C12 C3 C2 S1 179.3(6) . . . . ?
C12 C3 C2 N1 -5.9(12) . . . . ?
C2A S1A C5A C4A -27.3(4) . . . . ?
C2A S1A C5A C7A -152.9(5) . . . . ?
C2A S1A C5A C6A 88.5(5) . . . . ?
C2A N1A C11A C10A 150.1(8) . . . . ?
C2A N1A C8A C9A -148.9(7) . . . . ?
C3A C4A C5A S1A 33.4(6) . . . . ?
C3A C4A C5A C7A 160.1(5) . . . . ?
C3A C4A C5A C6A -81.8(6) . . . . ?
C18 C13 C4 C3 -153.2(7) . . . . ?
C18 C13 C4 C5 88.7(8) . . . . ?
C18 C13 C14 C15 -0.6(13) . . . . ?
C18 C17 C16 C15 -1.0(14) . . . . ?
C14A C13A C4A C3A -41.5(11) . . . . ?
C14A C13A C4A C5A 77.1(8) . . . . ?
C14A C13A C18A C17A -0.1(11) . . . . ?
C14A C15A C16A C17A -1.8(13) . . . . ?
C18A C13A C4A C3A 142.3(7) . . . . ?
C18A C13A C4A C5A -99.1(8) . . . . ?
C18A C13A C14A C15A 0.2(12) . . . . ?
C14 C13 C4 C3 27.4(11) . . . . ?
C14 C13 C4 C5 -90.7(8) . . . . ?
C14 C13 C18 C17 0.6(11) . . . . ?
C14 C15 C16 C17 1.1(15) . . . . ?
C3 C4 C5 S1 -34.7(6) . . . . ?
C3 C4 C5 C7 -160.8(6) . . . . ?
C3 C4 C5 C6 81.1(6) . . . . ?
C5A S1A C2A N1A -168.9(5) . . . . ?
C5A S1A C2A C3A 12.9(5) . . . . ?
C5A C4A C3A C2A -26.4(7) . . . . ?
C5A C4A C3A C12A 153.3(6) . . . . ?
C5 S1 C2 N1 170.0(5) . . . . ?
C5 S1 C2 C3 -14.4(5) . . . . ?
C5 C4 C3 C12 -157.7(6) . . . . ?
C5 C4 C3 C2 26.8(7) . . . . ?
C2 S1 C5 C4 28.7(5) . . . . ?
C2 S1 C5 C7 152.0(5) . . . . ?
C2 S1 C5 C6 -89.0(6) . . . . ?
C2 N1 C11 C10 -144.8(8) . . . . ?
C2 N1 C8 C9 145.5(8) . . . . ?
C15A C16A C17A C18A 1.9(13) . . . . ?
C6 C5 C7 O1 41.8(10) . . . . ?
C6 C5 C7 N4 -139.3(8) . . . . ?
C11 N1 C2 S1 177.2(6) . . . . ?
C11 N1 C2 C3 2.5(12) . . . . ?
C11 N1 C8 C9 -49.0(12) . . . . ?
C9A O2A C10A C11A -58.1(11) . . . . ?
C11A N1A C2A S1A -179.4(6) . . . . ?
C11A N1A C2A C3A -1.7(12) . . . . ?
C11A N1A C8A C9A 48.9(10) . . . . ?
C8A N1A C2A S1A 20.1(9) . . . . ?
C8A N1A C2A C3A -162.2(8) . . . . ?
C8A N1A C11A C10A -48.0(10) . . . . ?
C9 O2 C10 C11 56.0(12) . . . . ?
C10 O2 C9 C8 -55.9(13) . . . . ?
C8 N1 C2 S1 -19.0(11) . . . . ?
C8 N1 C2 C3 166.3(9) . . . . ?
C8 N1 C11 C10 50.0(11) . . . . ?
C10A O2A C9A C8A 58.9(11) . . . . ?


_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
;
####################################################################### 
# 
# 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_21
_database_code_depnum_ccdc_archive 'CCDC 2288490'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-03-21
_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         'C22 H20 N2 O2 S'
_chemical_formula_sum            'C22 H20 N2 O2 S'
_chemical_formula_weight         376.46
_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      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                   11.9036(6)
_cell_length_b                   12.3656(5)
_cell_length_c                   13.5444(6)
_cell_angle_alpha                82.460(4)
_cell_angle_beta                 80.987(4)
_cell_angle_gamma                79.478(4)
_cell_volume                     1925.11(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5635
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.5440
_cell_measurement_theta_min      3.9560
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21912
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.476
_diffrn_reflns_theta_min         3.607
_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 0.887
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00   4.00   1.00   60.00    --   21.29 -51.00 111.00   51
  2  ω    -32.00  -6.00   1.00   60.00    --  -22.70 -51.00 111.00   26
  3  ω    -73.00 -47.00   1.00   60.00    --  -22.70 -51.00 111.00   26
  4  ω    -42.00  45.00   1.00   60.00    --  -22.70  51.00-103.00   87
  5  ω     33.00  76.00   1.00   60.00    --   21.29  51.00-103.00   43
  6  ω    -47.00  40.00   1.00   60.00    --   21.29 -57.00  30.00   87
  7  ω    -88.00  -1.00   1.00   60.00    --  -22.70 -38.00 -90.00   87
  8  ω    -39.00   6.00   1.00   60.00    --  -22.70 -77.00 120.00   45
  9  ω    -39.00   5.00   1.00   60.00    --  -22.70 -77.00 -30.00   44
;
_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      -0.0085538000
_diffrn_orient_matrix_UB_12      0.0493736000
_diffrn_orient_matrix_UB_13      -0.0330258000
_diffrn_orient_matrix_UB_21      0.0589403000
_diffrn_orient_matrix_UB_22      0.0045240000
_diffrn_orient_matrix_UB_23      -0.0024173000
_diffrn_orient_matrix_UB_31      0.0139759000
_diffrn_orient_matrix_UB_32      -0.0313686000
_diffrn_orient_matrix_UB_33      -0.0417929000
_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                5875
_reflns_number_total             10398
_reflns_odcompleteness_completeness 98.81
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.362
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0060(13)
_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   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         10398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.007
_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)+(0.0798P)²+0.3080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21A(H21A,H21B), C19A(H19A,H19B), C19(H19C,H19D), C22(H22C,H22D), C21(H21C,
 H21D), C22A(H22A,H22B), C20(H20C,H20D), C20A(H20A,H20B)
;
_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
S1A S 0.76656(5) -0.01304(5) 0.54746(4) 0.04840(18) Uani 1 1 d . . . . .
S1 S 0.29438(5) 0.54408(5) 0.94811(4) 0.05074(19) Uani 1 1 d . . . . .
O1 O 0.45629(19) 0.76374(17) 0.88079(15) 0.0683(5) Uani 1 1 d . . . . .
O1A O 0.5943(2) -0.23206(17) 0.60859(15) 0.0745(6) Uani 1 1 d . . . . .
N1 N 0.09018(16) 0.67413(17) 0.98008(13) 0.0467(5) Uani 1 1 d . . . . .
N1A N 0.96517(17) -0.15418(16) 0.51971(14) 0.0478(5) Uani 1 1 d . . . . .
O2A O 1.02048(19) -0.30133(19) 0.36932(15) 0.0805(7) Uani 1 1 d . . . . .
O2 O -0.11480(17) 0.70750(19) 1.11715(14) 0.0797(7) Uani 1 1 d . . . . .
C12 C 0.31636(19) 0.59886(19) 0.68406(16) 0.0413(5) Uani 1 1 d . . . . .
C12A C 0.73033(19) -0.06286(18) 0.80607(16) 0.0406(5) Uani 1 1 d . . . . .
C2 C 0.19038(19) 0.65965(18) 0.91592(16) 0.0403(5) Uani 1 1 d . . . . .
C3A C 0.82268(19) -0.18861(18) 0.67096(16) 0.0422(5) Uani 1 1 d . . . . .
C3 C 0.22394(19) 0.71517(18) 0.82526(16) 0.0414(5) Uani 1 1 d . . . . .
C4 C 0.33534(19) 0.66193(18) 0.76704(15) 0.0391(5) Uani 1 1 d . . . . .
C2A C 0.8637(2) -0.13463(18) 0.58159(16) 0.0420(5) Uani 1 1 d . . . . .
C6 C 0.4987(2) 0.4983(2) 0.81714(16) 0.0446(5) Uani 1 1 d . . . . .
C4A C 0.71163(19) -0.12888(19) 0.72512(16) 0.0404(5) Uani 1 1 d . . . . .
C6A C 0.55094(19) 0.03026(19) 0.66429(16) 0.0436(5) Uani 1 1 d . . . . .
C5 C 0.40356(19) 0.59241(19) 0.84911(15) 0.0415(5) Uani 1 1 d . . . . .
C11A C 0.5512(2) 0.1404(2) 0.6294(2) 0.0503(6) Uani 1 1 d . . . . .
C17A C 0.8303(2) -0.0176(2) 0.80085(18) 0.0490(6) Uani 1 1 d . . . . .
C1 C 0.4567(2) 0.6671(2) 0.90280(18) 0.0507(6) Uani 1 1 d . . . . .
C5A C 0.65097(19) -0.06114(18) 0.63819(16) 0.0414(5) Uani 1 1 d . . . . .
C17 C 0.3767(2) 0.6125(3) 0.58920(18) 0.0595(7) Uani 1 1 d . . . . .
N2A N 0.9052(3) -0.3732(2) 0.7624(2) 0.0848(8) Uani 1 1 d . . . . .
C11 C 0.6031(2) 0.5251(3) 0.76838(19) 0.0564(7) Uani 1 1 d . . . . .
C1A C 0.6043(2) -0.1389(2) 0.5804(2) 0.0527(6) Uani 1 1 d . . . . .
C18A C 0.8718(2) -0.2907(2) 0.71839(18) 0.0534(6) Uani 1 1 d . . . . .
C18 C 0.1665(2) 0.8151(2) 0.78086(19) 0.0548(6) Uani 1 1 d . . . . .
C13 C 0.2375(3) 0.5265(2) 0.70016(19) 0.0572(7) Uani 1 1 d . . . . .
C7 C 0.4872(3) 0.3880(2) 0.8391(2) 0.0545(6) Uani 1 1 d . . . . .
C10A C 0.4549(2) 0.2194(2) 0.6531(2) 0.0595(7) Uani 1 1 d . . . . .
C15 C 0.2846(3) 0.4824(3) 0.5308(2) 0.0599(7) Uani 1 1 d . . . . .
C21A C 0.9727(2) -0.1134(2) 0.41223(18) 0.0558(6) Uani 1 1 d . . . . .
H21A H 1.049847 -0.098332 0.387314 0.067 Uiso 1 1 calc R U . . .
H21B H 0.918767 -0.045084 0.402849 0.067 Uiso 1 1 calc R U . . .
C19A C 1.0455(2) -0.2580(2) 0.5326(2) 0.0566(6) Uani 1 1 d . . . . .
H19A H 1.040181 -0.286292 0.603140 0.068 Uiso 1 1 calc R U . . .
H19B H 1.123877 -0.245425 0.509668 0.068 Uiso 1 1 calc R U . . .
C13A C 0.6481(2) -0.0481(3) 0.8900(2) 0.0606(7) Uani 1 1 d . . . . .
C9A C 0.3584(3) 0.1890(3) 0.7114(2) 0.0638(8) Uani 1 1 d . . . . .
C16A C 0.8458(3) 0.0414(3) 0.8763(2) 0.0634(7) Uani 1 1 d . . . . .
C19 C -0.0055(2) 0.7608(2) 0.95711(19) 0.0578(7) Uani 1 1 d . . . . .
H19C H -0.008584 0.770389 0.885299 0.069 Uiso 1 1 calc R U . . .
H19D H 0.006433 0.830179 0.976646 0.069 Uiso 1 1 calc R U . . .
C22 C 0.0890(2) 0.6398(2) 1.08827(18) 0.0562(6) Uani 1 1 d . . . . .
H22C H 0.109529 0.697919 1.120201 0.067 Uiso 1 1 calc R U . . .
H22D H 0.146072 0.573931 1.098204 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2220(3) 0.4687(2) 0.6242(2) 0.0637(8) Uani 1 1 d . . . . .
C8 C 0.5814(3) 0.3056(3) 0.8142(2) 0.0683(8) Uani 1 1 d . . . . .
N2 N 0.1261(2) 0.8977(2) 0.7405(2) 0.0969(10) Uani 1 1 d . . . . .
C15A C 0.7622(3) 0.0568(3) 0.9575(2) 0.0721(9) Uani 1 1 d . . . . .
C14A C 0.6647(3) 0.0115(3) 0.9644(2) 0.0763(10) Uani 1 1 d . . . . .
C9 C 0.6845(3) 0.3339(3) 0.7663(2) 0.0725(9) Uani 1 1 d . . . . .
C21 C -0.0267(2) 0.6167(3) 1.1359(2) 0.0660(8) Uani 1 1 d . . . . .
H21C H -0.042632 0.552326 1.110061 0.079 Uiso 1 1 calc R U . . .
H21D H -0.026635 0.599808 1.207890 0.079 Uiso 1 1 calc R U . . .
C16 C 0.3604(3) 0.5553(3) 0.5135(2) 0.0700(9) Uani 1 1 d . . . . .
C10 C 0.6953(3) 0.4424(3) 0.7435(2) 0.0672(8) Uani 1 1 d . . . . .
C7A C 0.4515(2) 0.0004(3) 0.7216(2) 0.0625(7) Uani 1 1 d . . . . .
C8A C 0.3563(3) 0.0796(3) 0.7453(2) 0.0711(8) Uani 1 1 d . . . . .
C22A C 0.9450(3) -0.1987(3) 0.3550(2) 0.0691(8) Uani 1 1 d . . . . .
H22A H 0.866002 -0.209676 0.377146 0.083 Uiso 1 1 calc R U . . .
H22B H 0.951717 -0.172331 0.283968 0.083 Uiso 1 1 calc R U . . .
C20 C -0.1170(2) 0.7315(3) 1.0120(2) 0.0763(9) Uani 1 1 d . . . . .
H20C H -0.178759 0.792700 0.999892 0.092 Uiso 1 1 calc R U . . .
H20D H -0.133418 0.667710 0.985615 0.092 Uiso 1 1 calc R U . . .
C20A C 1.0162(3) -0.3408(2) 0.4729(2) 0.0727(8) Uani 1 1 d . . . . .
H20A H 1.070100 -0.409379 0.480565 0.087 Uiso 1 1 calc R U . . .
H20B H 0.939393 -0.356253 0.498838 0.087 Uiso 1 1 calc R U . . .
H4A H 0.662(2) -0.179(2) 0.7568(18) 0.053(7) Uiso 1 1 d . . . . .
H4 H 0.3801(19) 0.7213(19) 0.7364(16) 0.041(6) Uiso 1 1 d . . . . .
H17A H 0.888(2) -0.031(2) 0.7469(18) 0.049(7) Uiso 1 1 d . . . . .
H13 H 0.191(2) 0.517(2) 0.762(2) 0.063(8) Uiso 1 1 d . . . . .
H1 H 0.490(2) 0.623(2) 0.960(2) 0.067(8) Uiso 1 1 d . . . . .
H1A H 0.580(3) -0.103(3) 0.521(2) 0.080(9) Uiso 1 1 d . . . . .
H11A H 0.623(3) 0.165(2) 0.587(2) 0.068(8) Uiso 1 1 d . . . . .
H7A H 0.449(3) -0.075(3) 0.739(2) 0.086(10) Uiso 1 1 d . . . . .
H15A H 0.774(3) 0.094(2) 1.015(2) 0.076(9) Uiso 1 1 d . . . . .
H7 H 0.415(2) 0.362(2) 0.8736(19) 0.059(8) Uiso 1 1 d . . . . .
H11 H 0.611(3) 0.603(3) 0.756(2) 0.094(11) Uiso 1 1 d . . . . .
H15 H 0.275(3) 0.440(3) 0.481(3) 0.096(11) Uiso 1 1 d . . . . .
H8 H 0.571(2) 0.232(3) 0.829(2) 0.070(9) Uiso 1 1 d . . . . .
H17 H 0.429(3) 0.656(2) 0.583(2) 0.065(8) Uiso 1 1 d . . . . .
H8A H 0.292(3) 0.063(2) 0.788(2) 0.075(9) Uiso 1 1 d . . . . .
H9A H 0.299(3) 0.242(2) 0.731(2) 0.064(8) Uiso 1 1 d . . . . .
H9 H 0.746(3) 0.273(3) 0.748(2) 0.096(11) Uiso 1 1 d . . . . .
H16A H 0.913(3) 0.075(3) 0.877(2) 0.093(11) Uiso 1 1 d . . . . .
H13A H 0.584(3) -0.082(2) 0.897(2) 0.069(9) Uiso 1 1 d . . . . .
H10A H 0.449(3) 0.301(3) 0.631(2) 0.089(10) Uiso 1 1 d . . . . .
H16 H 0.400(3) 0.563(2) 0.452(2) 0.076(9) Uiso 1 1 d . . . . .
H14 H 0.168(3) 0.422(3) 0.637(2) 0.078(10) Uiso 1 1 d . . . . .
H14A H 0.608(3) 0.015(3) 1.019(2) 0.085(10) Uiso 1 1 d . . . . .
H10 H 0.761(3) 0.464(3) 0.705(3) 0.092(11) 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
S1A C2A 1.778(2) . ?
S1A C5A 1.826(2) . ?
S1 C2 1.768(2) . ?
S1 C5 1.836(2) . ?
O1 C1 1.192(3) . ?
O1A C1A 1.186(3) . ?
N1 C2 1.359(3) . ?
N1 C19 1.456(3) . ?
N1 C22 1.470(3) . ?
N1A C2A 1.359(3) . ?
N1A C21A 1.471(3) . ?
N1A C19A 1.462(3) . ?
O2A C22A 1.425(3) . ?
O2A C20A 1.419(4) . ?
O2 C21 1.416(3) . ?
O2 C20 1.420(3) . ?
C12 C4 1.515(3) . ?
C12 C17 1.376(3) . ?
C12 C13 1.386(3) . ?
C12A C4A 1.515(3) . ?
C12A C17A 1.393(3) . ?
C12A C13A 1.387(3) . ?
C2 C3 1.365(3) . ?
C3A C2A 1.368(3) . ?
C3A C4A 1.521(3) . ?
C3A C18A 1.409(3) . ?
C3 C4 1.518(3) . ?
C3 C18 1.407(3) . ?
C4 C5 1.553(3) . ?
C4 H4 0.99(2) . ?
C6 C5 1.524(3) . ?
C6 C11 1.389(4) . ?
C6 C7 1.384(4) . ?
C4A C5A 1.548(3) . ?
C4A H4A 0.95(2) . ?
C6A C11A 1.382(3) . ?
C6A C5A 1.517(3) . ?
C6A C7A 1.392(4) . ?
C5 C1 1.522(3) . ?
C11A C10A 1.390(4) . ?
C11A H11A 1.03(3) . ?
C17A C16A 1.384(4) . ?
C17A H17A 0.93(2) . ?
C1 H1 0.98(3) . ?
C5A C1A 1.541(3) . ?
C17 C16 1.376(4) . ?
C17 H17 0.88(3) . ?
N2A C18A 1.149(3) . ?
C11 C10 1.389(4) . ?
C11 H11 0.97(3) . ?
C1A H1A 0.92(3) . ?
C18 N2 1.153(3) . ?
C13 C14 1.380(4) . ?
C13 H13 0.94(3) . ?
C7 C8 1.401(4) . ?
C7 H7 0.99(3) . ?
C10A C9A 1.371(4) . ?
C10A H10A 1.00(3) . ?
C15 C14 1.371(4) . ?
C15 C16 1.363(4) . ?
C15 H15 0.94(4) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C21A C22A 1.498(4) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A C20A 1.503(4) . ?
C13A C14A 1.381(4) . ?
C13A H13A 0.93(3) . ?
C9A C8A 1.374(4) . ?
C9A H9A 0.90(3) . ?
C16A C15A 1.370(4) . ?
C16A H16A 0.97(4) . ?
C19 H19C 0.9700 . ?
C19 H19D 0.9700 . ?
C19 C20 1.498(4) . ?
C22 H22C 0.9700 . ?
C22 H22D 0.9700 . ?
C22 C21 1.488(4) . ?
C14 H14 0.92(3) . ?
C8 C9 1.378(5) . ?
C8 H8 0.94(3) . ?
C15A C14A 1.364(5) . ?
C15A H15A 1.00(3) . ?
C14A H14A 0.91(3) . ?
C9 C10 1.362(5) . ?
C9 H9 0.98(4) . ?
C21 H21C 0.9700 . ?
C21 H21D 0.9700 . ?
C16 H16 0.89(3) . ?
C10 H10 0.93(3) . ?
C7A C8A 1.383(4) . ?
C7A H7A 0.93(3) . ?
C8A H8A 0.92(3) . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C20 H20C 0.9700 . ?
C20 H20D 0.9700 . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?

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
C2A S1A C5A 90.58(10) . . ?
C2 S1 C5 91.42(10) . . ?
C2 N1 C19 121.24(18) . . ?
C2 N1 C22 120.57(19) . . ?
C19 N1 C22 113.31(19) . . ?
C2A N1A C21A 120.6(2) . . ?
C2A N1A C19A 121.42(19) . . ?
C19A N1A C21A 109.20(19) . . ?
C20A O2A C22A 111.1(2) . . ?
C21 O2 C20 109.7(2) . . ?
C17 C12 C4 120.7(2) . . ?
C17 C12 C13 117.6(2) . . ?
C13 C12 C4 121.7(2) . . ?
C17A C12A C4A 122.0(2) . . ?
C13A C12A C4A 120.2(2) . . ?
C13A C12A C17A 117.7(2) . . ?
N1 C2 S1 116.37(15) . . ?
N1 C2 C3 131.3(2) . . ?
C3 C2 S1 112.21(17) . . ?
C2A C3A C4A 115.09(19) . . ?
C2A C3A C18A 127.8(2) . . ?
C18A C3A C4A 117.09(19) . . ?
C2 C3 C4 115.59(18) . . ?
C2 C3 C18 127.1(2) . . ?
C18 C3 C4 117.32(19) . . ?
C12 C4 C3 113.32(18) . . ?
C12 C4 C5 115.47(18) . . ?
C12 C4 H4 108.5(12) . . ?
C3 C4 C5 104.34(16) . . ?
C3 C4 H4 108.2(13) . . ?
C5 C4 H4 106.6(13) . . ?
N1A C2A S1A 116.44(16) . . ?
N1A C2A C3A 131.8(2) . . ?
C3A C2A S1A 111.61(17) . . ?
C11 C6 C5 118.0(2) . . ?
C7 C6 C5 122.9(2) . . ?
C7 C6 C11 119.1(2) . . ?
C12A C4A C3A 113.79(18) . . ?
C12A C4A C5A 115.56(18) . . ?
C12A C4A H4A 106.5(14) . . ?
C3A C4A C5A 103.19(17) . . ?
C3A C4A H4A 111.7(15) . . ?
C5A C4A H4A 105.9(15) . . ?
C11A C6A C5A 123.4(2) . . ?
C11A C6A C7A 118.6(2) . . ?
C7A C6A C5A 117.9(2) . . ?
C4 C5 S1 105.68(14) . . ?
C6 C5 S1 112.01(16) . . ?
C6 C5 C4 117.96(18) . . ?
C1 C5 S1 102.35(15) . . ?
C1 C5 C4 110.35(19) . . ?
C1 C5 C6 107.42(19) . . ?
C6A C11A C10A 120.4(3) . . ?
C6A C11A H11A 120.6(16) . . ?
C10A C11A H11A 118.9(16) . . ?
C12A C17A H17A 118.6(15) . . ?
C16A C17A C12A 120.9(3) . . ?
C16A C17A H17A 120.4(15) . . ?
O1 C1 C5 126.1(2) . . ?
O1 C1 H1 125.1(17) . . ?
C5 C1 H1 108.9(17) . . ?
C4A C5A S1A 105.21(15) . . ?
C6A C5A S1A 113.28(16) . . ?
C6A C5A C4A 118.02(18) . . ?
C6A C5A C1A 106.20(18) . . ?
C1A C5A S1A 103.26(16) . . ?
C1A C5A C4A 109.91(19) . . ?
C12 C17 H17 115.0(18) . . ?
C16 C17 C12 121.2(3) . . ?
C16 C17 H17 123.7(18) . . ?
C6 C11 H11 118(2) . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H11 122(2) . . ?
O1A C1A C5A 125.6(2) . . ?
O1A C1A H1A 122.9(19) . . ?
C5A C1A H1A 111.4(19) . . ?
N2A C18A C3A 175.1(3) . . ?
N2 C18 C3 175.6(3) . . ?
C12 C13 H13 121.3(17) . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 117.6(17) . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 123.9(16) . . ?
C8 C7 H7 116.3(16) . . ?
C11A C10A H10A 124.7(18) . . ?
C9A C10A C11A 120.4(3) . . ?
C9A C10A H10A 114.9(18) . . ?
C14 C15 H15 119(2) . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 122(2) . . ?
N1A C21A H21A 109.8 . . ?
N1A C21A H21B 109.8 . . ?
N1A C21A C22A 109.5(2) . . ?
H21A C21A H21B 108.2 . . ?
C22A C21A H21A 109.8 . . ?
C22A C21A H21B 109.8 . . ?
N1A C19A H19A 109.8 . . ?
N1A C19A H19B 109.8 . . ?
N1A C19A C20A 109.3(2) . . ?
H19A C19A H19B 108.3 . . ?
C20A C19A H19A 109.8 . . ?
C20A C19A H19B 109.8 . . ?
C12A C13A H13A 118.8(18) . . ?
C14A C13A C12A 120.6(3) . . ?
C14A C13A H13A 120.5(18) . . ?
C10A C9A C8A 119.9(3) . . ?
C10A C9A H9A 119.0(19) . . ?
C8A C9A H9A 121.0(19) . . ?
C17A C16A H16A 125(2) . . ?
C15A C16A C17A 120.3(3) . . ?
C15A C16A H16A 115(2) . . ?
N1 C19 H19C 109.6 . . ?
N1 C19 H19D 109.6 . . ?
N1 C19 C20 110.4(2) . . ?
H19C C19 H19D 108.1 . . ?
C20 C19 H19C 109.6 . . ?
C20 C19 H19D 109.6 . . ?
N1 C22 H22C 109.4 . . ?
N1 C22 H22D 109.4 . . ?
N1 C22 C21 111.0(2) . . ?
H22C C22 H22D 108.0 . . ?
C21 C22 H22C 109.4 . . ?
C21 C22 H22D 109.4 . . ?
C13 C14 H14 118.6(19) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 121.2(19) . . ?
C7 C8 H8 118.1(19) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 121.6(19) . . ?
C16A C15A H15A 121.4(17) . . ?
C14A C15A C16A 119.5(3) . . ?
C14A C15A H15A 118.9(17) . . ?
C13A C14A H14A 116(2) . . ?
C15A C14A C13A 121.0(3) . . ?
C15A C14A H14A 123(2) . . ?
C8 C9 H9 117(2) . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 123(2) . . ?
O2 C21 C22 111.9(2) . . ?
O2 C21 H21C 109.2 . . ?
O2 C21 H21D 109.2 . . ?
C22 C21 H21C 109.2 . . ?
C22 C21 H21D 109.2 . . ?
H21C C21 H21D 107.9 . . ?
C17 C16 H16 121(2) . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 118(2) . . ?
C11 C10 H10 117(2) . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 122(2) . . ?
C6A C7A H7A 118(2) . . ?
C8A C7A C6A 120.6(3) . . ?
C8A C7A H7A 121(2) . . ?
C9A C8A C7A 120.2(3) . . ?
C9A C8A H8A 117.6(19) . . ?
C7A C8A H8A 122(2) . . ?
O2A C22A C21A 111.4(2) . . ?
O2A C22A H22A 109.3 . . ?
O2A C22A H22B 109.3 . . ?
C21A C22A H22A 109.3 . . ?
C21A C22A H22B 109.3 . . ?
H22A C22A H22B 108.0 . . ?
O2 C20 C19 112.4(2) . . ?
O2 C20 H20C 109.1 . . ?
O2 C20 H20D 109.1 . . ?
C19 C20 H20C 109.1 . . ?
C19 C20 H20D 109.1 . . ?
H20C C20 H20D 107.8 . . ?
O2A C20A C19A 111.5(3) . . ?
O2A C20A H20A 109.3 . . ?
O2A C20A H20B 109.3 . . ?
C19A C20A H20A 109.3 . . ?
C19A C20A H20B 109.3 . . ?
H20A C20A H20B 108.0 . . ?

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
S1A C5A C1A O1A 126.1(3) . . . . ?
S1 C2 C3 C4 5.5(3) . . . . ?
S1 C2 C3 C18 -174.6(2) . . . . ?
S1 C5 C1 O1 -118.4(3) . . . . ?
N1 C2 C3 C4 -169.7(2) . . . . ?
N1 C2 C3 C18 10.2(4) . . . . ?
N1 C19 C20 O2 54.4(3) . . . . ?
N1 C22 C21 O2 -54.6(3) . . . . ?
N1A C21A C22A O2A -57.7(3) . . . . ?
N1A C19A C20A O2A 58.2(3) . . . . ?
C12 C4 C5 S1 -91.94(19) . . . . ?
C12 C4 C5 C6 34.2(3) . . . . ?
C12 C4 C5 C1 158.13(19) . . . . ?
C12 C17 C16 C15 -0.7(5) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C12A C4A C5A S1A 86.8(2) . . . . ?
C12A C4A C5A C6A -40.7(3) . . . . ?
C12A C4A C5A C1A -162.6(2) . . . . ?
C12A C17A C16A C15A -0.4(4) . . . . ?
C12A C13A C14A C15A -0.2(5) . . . . ?
C2 S1 C5 C4 -27.47(16) . . . . ?
C2 S1 C5 C6 -157.16(16) . . . . ?
C2 S1 C5 C1 88.06(16) . . . . ?
C2 N1 C19 C20 155.9(2) . . . . ?
C2 N1 C22 C21 -155.2(2) . . . . ?
C2 C3 C4 C12 100.5(2) . . . . ?
C2 C3 C4 C5 -25.9(3) . . . . ?
C3A C4A C5A S1A -38.05(19) . . . . ?
C3A C4A C5A C6A -165.5(2) . . . . ?
C3A C4A C5A C1A 72.5(2) . . . . ?
C3 C4 C5 S1 33.1(2) . . . . ?
C3 C4 C5 C6 159.2(2) . . . . ?
C3 C4 C5 C1 -76.8(2) . . . . ?
C4 C12 C17 C16 179.7(3) . . . . ?
C4 C12 C13 C14 -179.3(2) . . . . ?
C4 C5 C1 O1 -6.3(4) . . . . ?
C2A S1A C5A C4A 31.95(16) . . . . ?
C2A S1A C5A C6A 162.27(16) . . . . ?
C2A S1A C5A C1A -83.31(15) . . . . ?
C2A N1A C21A C22A -89.3(3) . . . . ?
C2A N1A C19A C20A 89.1(3) . . . . ?
C2A C3A C4A C12A -97.1(2) . . . . ?
C2A C3A C4A C5A 28.9(3) . . . . ?
C6 C5 C1 O1 123.6(3) . . . . ?
C6 C11 C10 C9 0.2(4) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C4A C12A C17A C16A -179.3(2) . . . . ?
C4A C12A C13A C14A 179.7(3) . . . . ?
C4A C3A C2A S1A -5.5(3) . . . . ?
C4A C3A C2A N1A 170.4(2) . . . . ?
C4A C5A C1A O1A 14.2(4) . . . . ?
C6A C11A C10A C9A 0.0(4) . . . . ?
C6A C5A C1A O1A -114.5(3) . . . . ?
C6A C7A C8A C9A 0.7(5) . . . . ?
C5 S1 C2 N1 -170.43(18) . . . . ?
C5 S1 C2 C3 13.61(18) . . . . ?
C5 C6 C11 C10 175.7(2) . . . . ?
C5 C6 C7 C8 -175.0(2) . . . . ?
C11A C6A C5A S1A -5.0(3) . . . . ?
C11A C6A C5A C4A 118.5(2) . . . . ?
C11A C6A C5A C1A -117.7(2) . . . . ?
C11A C6A C7A C8A -1.8(4) . . . . ?
C11A C10A C9A C8A -1.0(4) . . . . ?
C17A C12A C4A C3A 28.8(3) . . . . ?
C17A C12A C4A C5A -90.4(3) . . . . ?
C17A C12A C13A C14A 1.2(4) . . . . ?
C17A C16A C15A C14A 1.4(5) . . . . ?
C5A S1A C2A N1A 167.17(18) . . . . ?
C5A S1A C2A C3A -16.23(18) . . . . ?
C5A C6A C11A C10A 177.5(2) . . . . ?
C5A C6A C7A C8A -178.1(3) . . . . ?
C17 C12 C4 C3 133.0(2) . . . . ?
C17 C12 C4 C5 -106.7(3) . . . . ?
C17 C12 C13 C14 1.2(4) . . . . ?
C11 C6 C5 S1 -159.86(18) . . . . ?
C11 C6 C5 C4 77.2(3) . . . . ?
C11 C6 C5 C1 -48.2(3) . . . . ?
C11 C6 C7 C8 1.6(4) . . . . ?
C18A C3A C2A S1A 175.5(2) . . . . ?
C18A C3A C2A N1A -8.5(4) . . . . ?
C18A C3A C4A C12A 82.0(3) . . . . ?
C18A C3A C4A C5A -152.0(2) . . . . ?
C18 C3 C4 C12 -79.3(3) . . . . ?
C18 C3 C4 C5 154.2(2) . . . . ?
C13 C12 C4 C3 -46.4(3) . . . . ?
C13 C12 C4 C5 73.9(3) . . . . ?
C13 C12 C17 C16 -0.8(4) . . . . ?
C7 C6 C5 S1 16.8(3) . . . . ?
C7 C6 C5 C4 -106.2(3) . . . . ?
C7 C6 C5 C1 128.4(2) . . . . ?
C7 C6 C11 C10 -1.1(4) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C10A C9A C8A C7A 0.7(5) . . . . ?
C21A N1A C2A S1A -28.2(3) . . . . ?
C21A N1A C2A C3A 156.0(3) . . . . ?
C21A N1A C19A C20A -58.5(3) . . . . ?
C19A N1A C2A S1A -172.15(18) . . . . ?
C19A N1A C2A C3A 12.1(4) . . . . ?
C19A N1A C21A C22A 58.5(3) . . . . ?
C13A C12A C4A C3A -149.6(2) . . . . ?
C13A C12A C4A C5A 91.2(3) . . . . ?
C13A C12A C17A C16A -0.9(4) . . . . ?
C16A C15A C14A C13A -1.1(5) . . . . ?
C19 N1 C2 S1 -174.77(19) . . . . ?
C19 N1 C2 C3 0.3(4) . . . . ?
C19 N1 C22 C21 49.2(3) . . . . ?
C22 N1 C2 S1 31.6(3) . . . . ?
C22 N1 C2 C3 -153.4(3) . . . . ?
C22 N1 C19 C20 -48.7(3) . . . . ?
C14 C15 C16 C17 1.7(5) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C21 O2 C20 C19 -60.1(4) . . . . ?
C16 C15 C14 C13 -1.3(5) . . . . ?
C7A C6A C11A C10A 1.4(4) . . . . ?
C7A C6A C5A S1A 171.16(19) . . . . ?
C7A C6A C5A C4A -65.3(3) . . . . ?
C7A C6A C5A C1A 58.5(3) . . . . ?
C22A O2A C20A C19A -57.1(3) . . . . ?
C20 O2 C21 C22 60.0(3) . . . . ?
C20A O2A C22A C21A 57.0(3) . . . . ?


_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 1.133
_oxdiff_exptl_absorpt_empirical_full_min 0.900
####################################################################### 
# 
# 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_136
_database_code_depnum_ccdc_archive 'CCDC 2288495'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-08-23
_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         'C22 H24 N4 O2 S'
_chemical_formula_sum            'C22 H24 N4 O2 S'
_chemical_formula_weight         408.51
_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                   19.8227(18)
_cell_length_b                   8.1430(7)
_cell_length_c                   26.372(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.977(10)
_cell_angle_gamma                90
_cell_volume                     4148.2(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2297
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0640
_cell_measurement_theta_min      4.0180
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11495
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         3.763
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.962
_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  53.00   1.00   30.00    --   21.29-148.00   5.00   25
  2  ω     39.00  66.00   1.00   30.00    --   21.29-124.00 170.00   27
  3  ω    -77.00 -39.00   1.00   30.00    --  -22.70 124.00-110.00   38
  4  ω    -77.00 -51.00   1.00   30.00    --  -22.70 148.00  53.00   26
  5  ω     -1.00  92.00   1.00   30.00    --   21.29  38.00 120.00   93
  6  ω     35.00  87.00   1.00   30.00    --   21.29-178.00  60.00   52
  7  ω    -33.00 -22.00   1.00   30.00    --  -22.70 -77.00 -30.00   11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2527
_reflns_number_total             4953
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.305
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0014(3)
_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   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0648
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1999
_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:
 C17(H17A,H17B), C7(H7A,H7B), C14(H14A,H14B), C21(H21A,H21B), C16(H16A,H16B),
 C20(H20A,H20B), C22(H22A,H22B), C19(H19A,H19B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C12(H12), C11(H11), C10(H10)
;
_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 0.52727(4) 0.66083(9) 0.33335(4) 0.0526(3) Uani 1 1 d . . . . .
O1 O 0.38337(11) 0.6568(3) 0.33539(10) 0.0664(7) Uani 1 1 d . . . . .
N2 N 0.38912(13) 0.5461(3) 0.41462(11) 0.0507(7) Uani 1 1 d . . . . .
O4 O 0.77545(11) 0.6719(3) 0.29883(12) 0.0766(8) Uani 1 1 d . . . . .
N1 N 0.64559(11) 0.5619(3) 0.31147(12) 0.0586(8) Uani 1 1 d . . . . .
N3 N 0.56346(13) 0.5706(4) 0.47167(12) 0.0622(8) Uani 1 1 d . . . . .
C3 C 0.57238(13) 0.3597(3) 0.34473(12) 0.0434(7) Uani 1 1 d . . . . .
C4 C 0.50083(13) 0.3508(3) 0.35802(11) 0.0408(6) Uani 1 1 d . . . . .
C6 C 0.41535(14) 0.5840(4) 0.37379(12) 0.0454(7) Uani 1 1 d . . . . .
C8 C 0.32273(14) 0.7726(4) 0.44381(12) 0.0497(7) Uani 1 1 d . . . . .
C5 C 0.49097(13) 0.5289(3) 0.37652(12) 0.0423(7) Uani 1 1 d . . . . .
C00C C 0.53287(14) 0.5516(4) 0.43011(13) 0.0472(7) Uani 1 1 d . . . . .
C2 C 0.59067(12) 0.5104(4) 0.32945(12) 0.0460(7) Uani 1 1 d . . . . .
C17 C 0.44530(13) 0.2967(4) 0.31045(13) 0.0539(8) Uani 1 1 d . . . . .
H17A H 0.399525 0.329738 0.313884 0.065 Uiso 1 1 calc R U . . .
H17B H 0.454093 0.343280 0.278700 0.065 Uiso 1 1 calc R U . . .
C7 C 0.32128(13) 0.6049(4) 0.41958(14) 0.0564(9) Uani 1 1 d . . . . .
H7A H 0.302206 0.527294 0.440528 0.068 Uiso 1 1 calc R U . . .
H7B H 0.290586 0.607746 0.385303 0.068 Uiso 1 1 calc R U . . .
C14 C 0.49521(15) 0.2176(4) 0.39837(14) 0.0541(8) Uani 1 1 d . . . . .
H14A H 0.540478 0.193399 0.420060 0.065 Uiso 1 1 calc R U . . .
H14B H 0.465126 0.254104 0.420503 0.065 Uiso 1 1 calc R U . . .
N4 N 0.64227(14) 0.0941(4) 0.35141(17) 0.0876(12) Uani 1 1 d . . . . .
C18 C 0.61203(14) 0.2160(4) 0.34747(15) 0.0557(9) Uani 1 1 d . . . . .
C21 C 0.65598(15) 0.7314(4) 0.29791(16) 0.0604(9) Uani 1 1 d . . . . .
H21A H 0.626401 0.802723 0.312858 0.073 Uiso 1 1 calc R U . . .
H21B H 0.643622 0.744292 0.260395 0.073 Uiso 1 1 calc R U . . .
C13 C 0.38227(16) 0.8565(4) 0.46490(15) 0.0612(9) Uani 1 1 d . . . . .
H13 H 0.424798 0.808383 0.464829 0.073 Uiso 1 1 calc R U . . .
C9 C 0.26000(16) 0.8464(4) 0.44527(15) 0.0652(10) Uani 1 1 d . . . . .
H9 H 0.218842 0.790259 0.432451 0.078 Uiso 1 1 calc R U . . .
C16 C 0.45178(16) 0.1133(4) 0.31049(16) 0.0645(10) Uani 1 1 d . . . . .
H16A H 0.489953 0.079569 0.295413 0.077 Uiso 1 1 calc R U . . .
H16B H 0.409497 0.063015 0.290997 0.077 Uiso 1 1 calc R U . . .
C20 C 0.76632(15) 0.5098(5) 0.31410(17) 0.0718(11) Uani 1 1 d . . . . .
H20A H 0.777454 0.503500 0.351795 0.086 Uiso 1 1 calc R U . . .
H20B H 0.798017 0.438349 0.301355 0.086 Uiso 1 1 calc R U . . .
C22 C 0.73009(17) 0.7785(5) 0.31804(18) 0.0745(11) Uani 1 1 d . . . . .
H22A H 0.737030 0.890352 0.307626 0.089 Uiso 1 1 calc R U . . .
H22B H 0.741030 0.774496 0.355760 0.089 Uiso 1 1 calc R U . . .
C19 C 0.69415(15) 0.4513(4) 0.29389(18) 0.0730(12) Uani 1 1 d . . . . .
H19A H 0.683914 0.448480 0.256161 0.088 Uiso 1 1 calc R U . . .
H19B H 0.689171 0.340904 0.306375 0.088 Uiso 1 1 calc R U . . .
C15 C 0.4651(2) 0.0662(4) 0.36757(17) 0.0776(12) Uani 1 1 d . . . . .
H15A H 0.497588 -0.024577 0.374844 0.093 Uiso 1 1 calc R U . . .
H15B H 0.422361 0.033442 0.376736 0.093 Uiso 1 1 calc R U . . .
C12 C 0.3807(2) 1.0107(5) 0.48624(18) 0.0809(12) Uani 1 1 d . . . . .
H12 H 0.421736 1.065510 0.500545 0.097 Uiso 1 1 calc R U . . .
C11 C 0.3181(2) 1.0823(5) 0.4862(2) 0.0904(14) Uani 1 1 d . . . . .
H11 H 0.316592 1.186501 0.500287 0.109 Uiso 1 1 calc R U . . .
C10 C 0.2582(2) 1.0013(5) 0.46545(19) 0.0854(13) Uani 1 1 d . . . . .
H10 H 0.215814 1.051071 0.464982 0.102 Uiso 1 1 calc R U . . .
H2 H 0.4138(17) 0.504(4) 0.4403(16) 0.079(13) 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 C5 1.827(3) . ?
S1 C2 1.774(3) . ?
O1 C6 1.221(4) . ?
N2 C6 1.333(4) . ?
N2 C7 1.461(3) . ?
N2 H2 0.82(4) . ?
O4 C20 1.404(4) . ?
O4 C22 1.422(4) . ?
N1 C2 1.348(3) . ?
N1 C21 1.452(4) . ?
N1 C19 1.467(4) . ?
N3 C00C 1.138(4) . ?
C3 C4 1.537(4) . ?
C3 C2 1.366(4) . ?
C3 C18 1.402(4) . ?
C4 C5 1.556(4) . ?
C4 C17 1.536(4) . ?
C4 C14 1.541(4) . ?
C6 C5 1.551(4) . ?
C8 C7 1.505(4) . ?
C8 C13 1.369(4) . ?
C8 C9 1.389(4) . ?
C5 C00C 1.481(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.499(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.522(5) . ?
N4 C18 1.152(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.496(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.518(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.488(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C11 1.371(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.362(5) . ?
C10 H10 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 C5 90.77(13) . . ?
C6 N2 C7 122.0(3) . . ?
C6 N2 H2 120(3) . . ?
C7 N2 H2 117(3) . . ?
C20 O4 C22 109.8(3) . . ?
C2 N1 C21 123.5(2) . . ?
C2 N1 C19 124.0(3) . . ?
C21 N1 C19 111.5(3) . . ?
C2 C3 C4 115.4(2) . . ?
C2 C3 C18 125.6(3) . . ?
C18 C3 C4 119.0(2) . . ?
C3 C4 C5 102.4(2) . . ?
C3 C4 C14 113.8(2) . . ?
C17 C4 C3 110.9(2) . . ?
C17 C4 C5 114.0(2) . . ?
C17 C4 C14 102.3(2) . . ?
C14 C4 C5 113.9(2) . . ?
O1 C6 N2 124.0(3) . . ?
O1 C6 C5 119.7(3) . . ?
N2 C6 C5 116.3(3) . . ?
C13 C8 C7 123.9(3) . . ?
C13 C8 C9 117.9(3) . . ?
C9 C8 C7 118.2(3) . . ?
C4 C5 S1 104.9(2) . . ?
C6 C5 S1 108.22(19) . . ?
C6 C5 C4 116.3(2) . . ?
C00C C5 S1 107.84(19) . . ?
C00C C5 C4 109.4(2) . . ?
C00C C5 C6 109.7(3) . . ?
N3 C00C C5 178.1(3) . . ?
N1 C2 S1 116.4(2) . . ?
N1 C2 C3 132.2(3) . . ?
C3 C2 S1 111.4(2) . . ?
C4 C17 H17A 111.0 . . ?
C4 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C16 C17 C4 103.9(3) . . ?
C16 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
N2 C7 C8 113.9(2) . . ?
N2 C7 H7A 108.8 . . ?
N2 C7 H7B 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C4 C14 H14A 110.5 . . ?
C4 C14 H14B 110.5 . . ?
H14A C14 H14B 108.6 . . ?
C15 C14 C4 106.4(3) . . ?
C15 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
N4 C18 C3 176.1(4) . . ?
N1 C21 H21A 109.7 . . ?
N1 C21 H21B 109.7 . . ?
N1 C21 C22 109.8(3) . . ?
H21A C21 H21B 108.2 . . ?
C22 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
C8 C13 H13 119.2 . . ?
C8 C13 C12 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
C17 C16 C15 104.4(3) . . ?
H16A C16 H16B 108.9 . . ?
C15 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
O4 C20 H20A 109.2 . . ?
O4 C20 H20B 109.2 . . ?
O4 C20 C19 111.9(3) . . ?
H20A C20 H20B 107.9 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
O4 C22 C21 111.5(3) . . ?
O4 C22 H22A 109.3 . . ?
O4 C22 H22B 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
N1 C19 C20 109.7(3) . . ?
N1 C19 H19A 109.7 . . ?
N1 C19 H19B 109.7 . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C14 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
C16 C15 C14 106.5(3) . . ?
C16 C15 H15A 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C13 C12 H12 120.3 . . ?
C11 C12 C13 119.3(4) . . ?
C11 C12 H12 120.3 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C5 S1 24.0(3) . . . . ?
O1 C6 C5 C4 -93.7(3) . . . . ?
O1 C6 C5 C00C 141.4(3) . . . . ?
N2 C6 C5 S1 -156.5(2) . . . . ?
N2 C6 C5 C4 85.7(3) . . . . ?
N2 C6 C5 C00C -39.1(4) . . . . ?
O4 C20 C19 N1 -57.0(5) . . . . ?
N1 C21 C22 O4 56.7(4) . . . . ?
C3 C4 C5 S1 38.6(2) . . . . ?
C3 C4 C5 C6 158.1(3) . . . . ?
C3 C4 C5 C00C -76.9(3) . . . . ?
C3 C4 C17 C16 82.3(3) . . . . ?
C3 C4 C14 C15 -94.8(3) . . . . ?
C4 C3 C2 S1 3.9(3) . . . . ?
C4 C3 C2 N1 -174.4(3) . . . . ?
C4 C17 C16 C15 39.1(3) . . . . ?
C4 C14 C15 C16 -1.6(4) . . . . ?
C6 N2 C7 C8 -85.9(4) . . . . ?
C8 C13 C12 C11 -0.3(7) . . . . ?
C8 C9 C10 C11 -2.5(7) . . . . ?
C5 S1 C2 N1 -163.4(2) . . . . ?
C5 S1 C2 C3 18.1(2) . . . . ?
C5 C4 C17 C16 -162.8(3) . . . . ?
C5 C4 C14 C15 148.3(2) . . . . ?
C2 S1 C5 C4 -33.53(18) . . . . ?
C2 S1 C5 C6 -158.4(2) . . . . ?
C2 S1 C5 C00C 83.0(2) . . . . ?
C2 N1 C21 C22 137.1(3) . . . . ?
C2 N1 C19 C20 -137.2(3) . . . . ?
C2 C3 C4 C5 -28.3(3) . . . . ?
C2 C3 C4 C17 93.6(3) . . . . ?
C2 C3 C4 C14 -151.8(3) . . . . ?
C17 C4 C5 S1 -81.2(2) . . . . ?
C17 C4 C5 C6 38.3(4) . . . . ?
C17 C4 C5 C00C 163.3(2) . . . . ?
C17 C4 C14 C15 24.8(3) . . . . ?
C17 C16 C15 C14 -23.1(4) . . . . ?
C7 N2 C6 O1 -7.0(5) . . . . ?
C7 N2 C6 C5 173.6(3) . . . . ?
C7 C8 C13 C12 179.4(4) . . . . ?
C7 C8 C9 C10 -178.0(4) . . . . ?
C14 C4 C5 S1 161.94(18) . . . . ?
C14 C4 C5 C6 -78.5(3) . . . . ?
C14 C4 C5 C00C 46.5(3) . . . . ?
C14 C4 C17 C16 -39.4(3) . . . . ?
C18 C3 C4 C5 153.6(3) . . . . ?
C18 C3 C4 C17 -84.4(3) . . . . ?
C18 C3 C4 C14 30.2(4) . . . . ?
C18 C3 C2 S1 -178.2(3) . . . . ?
C18 C3 C2 N1 3.5(6) . . . . ?
C21 N1 C2 S1 2.8(4) . . . . ?
C21 N1 C2 C3 -179.0(3) . . . . ?
C21 N1 C19 C20 53.8(4) . . . . ?
C13 C8 C7 N2 -7.1(5) . . . . ?
C13 C8 C9 C10 2.5(6) . . . . ?
C13 C12 C11 C10 0.4(7) . . . . ?
C9 C8 C7 N2 173.4(3) . . . . ?
C9 C8 C13 C12 -1.1(6) . . . . ?
C20 O4 C22 C21 -59.6(4) . . . . ?
C22 O4 C20 C19 59.9(4) . . . . ?
C19 N1 C2 S1 -164.9(3) . . . . ?
C19 N1 C2 C3 13.3(6) . . . . ?
C19 N1 C21 C22 -53.9(4) . . . . ?
C12 C11 C10 C9 1.0(8) . . . . ?


_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
;
####################################################################### 
# 
# 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_81
_database_code_depnum_ccdc_archive 'CCDC 2288493'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-05-26
_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         'C32 H29 N3 O3 S'
_chemical_formula_sum            'C32 H29 N3 O3 S'
_chemical_formula_weight         535.64
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.1630(12)
_cell_length_b                   11.7627(8)
_cell_length_c                   18.6294(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.090(8)
_cell_angle_gamma                90
_cell_volume                     2848.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3792
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.6160
_cell_measurement_theta_min      3.7210
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22624
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.498
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  47.00   1.00   90.00    --   21.29 -11.00-124.00   98
  2  ω     -2.00  23.00   1.00   90.00    --   21.29  11.00  48.00   25
  3  ω    -46.00 -21.00   1.00   90.00    --  -22.70  11.00  48.00   25
  4  ω    -37.00 -12.00   1.00   90.00    --  -22.70 -11.00-124.00   25
  5  ω      3.00  88.00   1.00   90.00    --   21.29  57.00  60.00   85
  6  ω     39.00  95.00   1.00   90.00    --   21.29 178.00-150.00   56
  7  ω    -38.00   4.00   1.00   90.00    --  -22.70 -77.00-180.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3614
_reflns_number_total             7713
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.279
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         7713
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1603
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.012
_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)+(0.1000P)²+0.0500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.2342
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
C00F C 0.0766(2) 0.8826(2) 0.22514(16) 0.0480(7) Uani 1 1 d . . . . .
C2 C 0.1559(2) 0.7036(2) 0.18926(15) 0.0425(6) Uani 1 1 d . . . . .
C3 C 0.1479(2) 0.7926(2) 0.23591(15) 0.0425(6) Uani 1 1 d . . . . .
C4 C 0.2144(2) 0.7845(2) 0.30996(16) 0.0439(7) Uani 1 1 d . . . . .
H4 H 0.248(2) 0.864(2) 0.3246(14) 0.039(7) Uiso 1 1 d . . . . .
C5 C 0.3062(2) 0.7047(2) 0.29878(15) 0.0420(6) Uani 1 1 d . . . . .
C6 C 0.3486(2) 0.6437(2) 0.37109(15) 0.0468(7) Uani 1 1 d . . . . .
C7 C 0.3004(3) 0.5383(3) 0.39013(17) 0.0510(7) Uani 1 1 d . . . . .
H7 H 0.256(2) 0.504(2) 0.3513(17) 0.048(8) Uiso 1 1 d . . . . .
C8 C 0.3203(3) 0.4932(3) 0.45645(18) 0.0589(8) Uani 1 1 d . . . . .
H8 H 0.376(3) 0.542(3) 0.4928(19) 0.071(10) Uiso 1 1 d . . . . .
C9 C 0.2756(3) 0.3896(3) 0.48118(18) 0.0605(9) Uani 1 1 d . . . . .
C10 C 0.2023(3) 0.3255(3) 0.4372(2) 0.0679(10) Uani 1 1 d . . . . .
H10 H 0.178469 0.349871 0.390048 0.081 Uiso 1 1 calc R U . . .
C11 C 0.1640(4) 0.2260(3) 0.4619(2) 0.0828(12) Uani 1 1 d . . . . .
H11 H 0.114902 0.184878 0.431059 0.099 Uiso 1 1 calc R U . . .
C12 C 0.1968(4) 0.1864(3) 0.5314(3) 0.0848(12) Uani 1 1 d . . . . .
C13 C 0.2694(4) 0.2497(4) 0.5751(3) 0.1026(15) Uani 1 1 d . . . . .
H13 H 0.292862 0.224774 0.622212 0.123 Uiso 1 1 calc R U . . .
C14 C 0.3085(3) 0.3489(4) 0.5515(2) 0.0847(12) Uani 1 1 d . . . . .
H14 H 0.357626 0.389392 0.582727 0.102 Uiso 1 1 calc R U . . .
C15 C 0.1531(5) 0.0784(4) 0.5594(4) 0.137(2) Uani 1 1 d . . . . .
H15A H 0.100849 0.097818 0.587887 0.205 Uiso 1 1 calc R U . . .
H15B H 0.207094 0.037084 0.588979 0.205 Uiso 1 1 calc R U . . .
H15C H 0.123633 0.032025 0.518996 0.205 Uiso 1 1 calc R U . . .
C16 C 0.1551(2) 0.7462(2) 0.36942(16) 0.0495(7) Uani 1 1 d . . . . .
C17 C 0.1825(3) 0.7889(3) 0.43904(18) 0.0640(9) Uani 1 1 d . . . . .
H17 H 0.233148 0.844551 0.447802 0.077 Uiso 1 1 calc R U . . .
C18 C 0.1354(4) 0.7498(4) 0.4960(2) 0.0861(12) Uani 1 1 d . . . . .
H18 H 0.155021 0.778520 0.542619 0.103 Uiso 1 1 calc R U . . .
C19 C 0.0603(4) 0.6694(4) 0.4833(3) 0.0945(14) Uani 1 1 d . . . . .
H19 H 0.029584 0.642060 0.521498 0.113 Uiso 1 1 calc R U . . .
C20 C 0.0297(4) 0.6285(4) 0.4141(3) 0.0882(12) Uani 1 1 d . . . . .
H20 H -0.022960 0.575155 0.405373 0.106 Uiso 1 1 calc R U . . .
C21 C 0.0773(3) 0.6669(3) 0.3574(2) 0.0659(9) Uani 1 1 d . . . . .
H21 H 0.056529 0.638712 0.310761 0.079 Uiso 1 1 calc R U . . .
C22 C 0.5636(2) 0.7564(2) 0.23485(16) 0.0496(7) Uani 1 1 d . . . . .
C23 C 0.6413(3) 0.6791(3) 0.2325(2) 0.0793(12) Uani 1 1 d . . . . .
H23 H 0.630498 0.602659 0.241500 0.095 Uiso 1 1 calc R U . . .
C24 C 0.7351(4) 0.7146(4) 0.2169(3) 0.1024(17) Uani 1 1 d . . . . .
H24 H 0.787388 0.661740 0.215921 0.123 Uiso 1 1 calc R U . . .
C25 C 0.7525(3) 0.8262(4) 0.2027(3) 0.0935(14) Uani 1 1 d . . . . .
H25 H 0.816581 0.850236 0.193541 0.112 Uiso 1 1 calc R U . . .
C26 C 0.6741(4) 0.9011(3) 0.2023(3) 0.0845(13) Uani 1 1 d . . . . .
H26 H 0.684619 0.976754 0.191012 0.101 Uiso 1 1 calc R U . . .
C27 C 0.5795(3) 0.8691(3) 0.2181(2) 0.0706(10) Uani 1 1 d . . . . .
H27 H 0.527053 0.922270 0.217442 0.085 Uiso 1 1 calc R U . . .
C28 C 0.3917(2) 0.7748(2) 0.27176(14) 0.0429(7) Uani 1 1 d . . . . .
C29 C 0.0245(3) 0.7494(3) 0.08318(17) 0.0586(9) Uani 1 1 d . . . . .
H29A H 0.034377 0.756926 0.032879 0.070 Uiso 1 1 calc R U . . .
H29B H 0.026933 0.824804 0.104494 0.070 Uiso 1 1 calc R U . . .
C30 C -0.0775(3) 0.6965(3) 0.0865(2) 0.0708(10) Uani 1 1 d . . . . .
H30A H -0.089185 0.694089 0.136563 0.085 Uiso 1 1 calc R U . . .
H30B H -0.131278 0.742508 0.059046 0.085 Uiso 1 1 calc R U . . .
C31 C 0.1011(3) 0.5650(3) 0.09266(17) 0.0608(9) Uani 1 1 d . . . . .
H31A H 0.153772 0.518102 0.120545 0.073 Uiso 1 1 calc R U . . .
H31B H 0.113211 0.566702 0.042647 0.073 Uiso 1 1 calc R U . . .
C32 C -0.0039(3) 0.5158(3) 0.0962(2) 0.0750(11) Uani 1 1 d . . . . .
H32A H -0.008116 0.439790 0.075709 0.090 Uiso 1 1 calc R U . . .
H32B H -0.013769 0.510107 0.146581 0.090 Uiso 1 1 calc R U . . .
N1 N 0.1058(2) 0.6799(2) 0.12227(13) 0.0526(7) Uani 1 1 d . . . . .
N2 N 0.0219(2) 0.9604(2) 0.22036(17) 0.0678(8) Uani 1 1 d . . . . .
N3 N 0.4716(2) 0.7147(2) 0.25511(15) 0.0522(7) Uani 1 1 d . . . . .
H3 H 0.469(3) 0.648(3) 0.2595(19) 0.068(11) Uiso 1 1 d . . . . .
O1 O 0.41815(18) 0.69152(19) 0.41064(12) 0.0662(6) Uani 1 1 d . . . . .
O2 O 0.38458(18) 0.87768(17) 0.26573(14) 0.0656(7) Uani 1 1 d . . . . .
O3 O -0.08250(19) 0.5842(2) 0.05756(14) 0.0728(7) Uani 1 1 d . . . . .
S1 S 0.25237(6) 0.60613(5) 0.22627(4) 0.0453(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C00F C3 1.407(4) . ?
C00F N2 1.159(4) . ?
C2 C3 1.376(4) . ?
C2 N1 1.345(3) . ?
C2 S1 1.767(3) . ?
C3 C4 1.516(4) . ?
C4 H4 1.05(3) . ?
C4 C5 1.570(4) . ?
C4 C16 1.521(4) . ?
C5 C6 1.550(4) . ?
C5 C28 1.543(4) . ?
C5 S1 1.835(3) . ?
C6 C7 1.461(4) . ?
C6 O1 1.218(3) . ?
C7 H7 0.95(3) . ?
C7 C8 1.332(4) . ?
C8 H8 1.08(3) . ?
C8 C9 1.460(5) . ?
C9 C10 1.386(5) . ?
C9 C14 1.398(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(6) . ?
C12 C13 1.374(6) . ?
C12 C15 1.520(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.384(4) . ?
C16 C21 1.377(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.362(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.374(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(5) . ?
C22 C27 1.386(4) . ?
C22 N3 1.411(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.365(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.357(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.376(5) . ?
C27 H27 0.9300 . ?
C28 N3 1.344(4) . ?
C28 O2 1.217(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.491(5) . ?
C29 N1 1.448(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 O3 1.423(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.509(5) . ?
C31 N1 1.458(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 O3 1.415(4) . ?
N3 H3 0.80(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C00F C3 175.3(3) . . ?
C3 C2 S1 111.7(2) . . ?
N1 C2 C3 131.9(3) . . ?
N1 C2 S1 116.4(2) . . ?
C00F C3 C4 117.0(2) . . ?
C2 C3 C00F 126.8(3) . . ?
C2 C3 C4 115.8(2) . . ?
C3 C4 H4 109.8(14) . . ?
C3 C4 C5 105.3(2) . . ?
C3 C4 C16 113.1(2) . . ?
C5 C4 H4 105.5(15) . . ?
C16 C4 H4 108.4(14) . . ?
C16 C4 C5 114.5(2) . . ?
C4 C5 S1 105.06(18) . . ?
C6 C5 C4 109.9(2) . . ?
C6 C5 S1 113.05(18) . . ?
C28 C5 C4 109.9(2) . . ?
C28 C5 C6 110.5(2) . . ?
C28 C5 S1 108.33(19) . . ?
C7 C6 C5 119.5(2) . . ?
O1 C6 C5 116.4(3) . . ?
O1 C6 C7 124.0(3) . . ?
C6 C7 H7 114.9(18) . . ?
C8 C7 C6 122.3(3) . . ?
C8 C7 H7 122.9(18) . . ?
C7 C8 H8 112.6(18) . . ?
C7 C8 C9 126.5(3) . . ?
C9 C8 H8 120.9(18) . . ?
C10 C9 C8 123.1(3) . . ?
C10 C9 C14 116.9(3) . . ?
C14 C9 C8 120.1(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.3(4) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.5(4) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C15 121.7(5) . . ?
C13 C12 C11 117.3(4) . . ?
C13 C12 C15 121.0(4) . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.1(4) . . ?
C14 C13 H13 119.0 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.0(4) . . ?
C13 C14 H14 119.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C4 119.2(3) . . ?
C21 C16 C4 122.4(3) . . ?
C21 C16 C17 118.4(3) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.9(4) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.7(4) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C27 119.1(3) . . ?
C23 C22 N3 117.0(3) . . ?
C27 C22 N3 124.0(3) . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(4) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.1(4) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 120.8 . . ?
C26 C25 C24 118.3(4) . . ?
C26 C25 H25 120.8 . . ?
C25 C26 H26 118.8 . . ?
C25 C26 C27 122.3(4) . . ?
C27 C26 H26 118.8 . . ?
C22 C27 H27 120.5 . . ?
C26 C27 C22 118.9(4) . . ?
C26 C27 H27 120.5 . . ?
N3 C28 C5 115.6(2) . . ?
O2 C28 C5 120.8(3) . . ?
O2 C28 N3 123.6(3) . . ?
H29A C29 H29B 108.2 . . ?
C30 C29 H29A 109.7 . . ?
C30 C29 H29B 109.7 . . ?
N1 C29 H29A 109.7 . . ?
N1 C29 H29B 109.7 . . ?
N1 C29 C30 110.0(3) . . ?
C29 C30 H30A 109.4 . . ?
C29 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?
O3 C30 C29 111.1(3) . . ?
O3 C30 H30A 109.4 . . ?
O3 C30 H30B 109.4 . . ?
H31A C31 H31B 108.3 . . ?
C32 C31 H31A 109.9 . . ?
C32 C31 H31B 109.9 . . ?
N1 C31 H31A 109.9 . . ?
N1 C31 H31B 109.9 . . ?
N1 C31 C32 108.9(3) . . ?
C31 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
O3 C32 C31 111.1(3) . . ?
O3 C32 H32A 109.4 . . ?
O3 C32 H32B 109.4 . . ?
C2 N1 C29 124.4(2) . . ?
C2 N1 C31 121.9(2) . . ?
C29 N1 C31 110.4(2) . . ?
C22 N3 H3 115(3) . . ?
C28 N3 C22 128.0(3) . . ?
C28 N3 H3 116(3) . . ?
C32 O3 C30 110.4(3) . . ?
C2 S1 C5 92.72(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
C00F C3 C4 C5 -162.7(2) . . . . ?
C00F C3 C4 C16 71.6(3) . . . . ?
C2 C3 C4 C5 24.3(3) . . . . ?
C2 C3 C4 C16 -101.4(3) . . . . ?
C3 C2 N1 C29 -1.4(5) . . . . ?
C3 C2 N1 C31 -158.8(3) . . . . ?
C3 C2 S1 C5 -13.1(2) . . . . ?
C3 C4 C5 C6 -152.9(2) . . . . ?
C3 C4 C5 C28 85.3(2) . . . . ?
C3 C4 C5 S1 -31.0(2) . . . . ?
C3 C4 C16 C17 -146.0(3) . . . . ?
C3 C4 C16 C21 36.6(4) . . . . ?
C4 C5 C6 C7 85.4(3) . . . . ?
C4 C5 C6 O1 -90.8(3) . . . . ?
C4 C5 C28 N3 -175.4(2) . . . . ?
C4 C5 C28 O2 3.8(3) . . . . ?
C4 C5 S1 C2 25.7(2) . . . . ?
C4 C16 C17 C18 -175.2(3) . . . . ?
C4 C16 C21 C20 175.6(3) . . . . ?
C5 C4 C16 C17 93.4(3) . . . . ?
C5 C4 C16 C21 -83.9(3) . . . . ?
C5 C6 C7 C8 -167.4(3) . . . . ?
C5 C28 N3 C22 -174.5(3) . . . . ?
C6 C5 C28 N3 63.1(3) . . . . ?
C6 C5 C28 O2 -117.6(3) . . . . ?
C6 C5 S1 C2 145.6(2) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 C10 -1.9(6) . . . . ?
C7 C8 C9 C14 176.2(4) . . . . ?
C8 C9 C10 C11 178.1(3) . . . . ?
C8 C9 C14 C13 -178.2(4) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C9 C14 C13 0.0(6) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C10 C11 C12 C15 178.6(4) . . . . ?
C11 C12 C13 C14 0.1(7) . . . . ?
C12 C13 C14 C9 0.0(7) . . . . ?
C14 C9 C10 C11 0.0(6) . . . . ?
C15 C12 C13 C14 -178.7(5) . . . . ?
C16 C4 C5 C6 -28.1(3) . . . . ?
C16 C4 C5 C28 -149.8(2) . . . . ?
C16 C4 C5 S1 93.8(2) . . . . ?
C16 C17 C18 C19 -0.8(6) . . . . ?
C17 C16 C21 C20 -1.7(5) . . . . ?
C17 C18 C19 C20 -1.3(7) . . . . ?
C18 C19 C20 C21 1.8(7) . . . . ?
C19 C20 C21 C16 -0.3(6) . . . . ?
C21 C16 C17 C18 2.3(5) . . . . ?
C22 C23 C24 C25 -0.7(8) . . . . ?
C23 C22 C27 C26 -2.5(6) . . . . ?
C23 C22 N3 C28 169.2(3) . . . . ?
C23 C24 C25 C26 -1.9(8) . . . . ?
C24 C25 C26 C27 2.3(8) . . . . ?
C25 C26 C27 C22 -0.1(7) . . . . ?
C27 C22 C23 C24 2.9(6) . . . . ?
C27 C22 N3 C28 -10.3(5) . . . . ?
C28 C5 C6 C7 -153.2(3) . . . . ?
C28 C5 C6 O1 30.6(4) . . . . ?
C28 C5 S1 C2 -91.6(2) . . . . ?
C29 C30 O3 C32 58.4(4) . . . . ?
C30 C29 N1 C2 -102.5(3) . . . . ?
C30 C29 N1 C31 57.2(4) . . . . ?
C31 C32 O3 C30 -58.8(4) . . . . ?
C32 C31 N1 C2 103.4(3) . . . . ?
C32 C31 N1 C29 -56.9(3) . . . . ?
N1 C2 C3 C00F 3.9(5) . . . . ?
N1 C2 C3 C4 176.2(3) . . . . ?
N1 C2 S1 C5 165.9(2) . . . . ?
N1 C29 C30 O3 -57.6(4) . . . . ?
N1 C31 C32 O3 58.0(4) . . . . ?
N3 C22 C23 C24 -176.6(4) . . . . ?
N3 C22 C27 C26 177.0(4) . . . . ?
O1 C6 C7 C8 8.5(5) . . . . ?
O2 C28 N3 C22 6.2(5) . . . . ?
S1 C2 C3 C00F -177.2(2) . . . . ?
S1 C2 C3 C4 -5.0(3) . . . . ?
S1 C2 N1 C29 179.9(2) . . . . ?
S1 C2 N1 C31 22.4(4) . . . . ?
S1 C5 C6 C7 -31.6(3) . . . . ?
S1 C5 C6 O1 152.2(2) . . . . ?
S1 C5 C28 N3 -61.2(3) . . . . ?
S1 C5 C28 O2 118.1(3) . . . . ?


_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
;
