# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_226
_database_code_depnum_ccdc_archive 'CCDC 2232175'
loop_
_audit_author_name
_audit_author_address
dd
;ff
China
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N3 O2 S'
_chemical_formula_sum            'C23 H25 N3 O2 S'
_chemical_formula_weight         407.52
_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      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   20.8691(8)
_cell_length_b                   20.8691(8)
_cell_length_c                   10.3768(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4519.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4440
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.4150
_cell_measurement_theta_min      2.1970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8173
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.499
_diffrn_reflns_theta_min         2.192
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  76.00   1.00    2.50    --   12.05  38.00-180.00   27
  2  ω    -20.00  63.00   1.00    2.50    --   12.05  77.00-120.00   83
  3  ω     -2.00  23.00   1.00    2.50    --   11.90  77.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0007835000
_diffrn_orient_matrix_UB_12      0.0116515000
_diffrn_orient_matrix_UB_13      -0.0641355000
_diffrn_orient_matrix_UB_21      -0.0055058000
_diffrn_orient_matrix_UB_22      0.0315732000
_diffrn_orient_matrix_UB_23      0.0229191000
_diffrn_orient_matrix_UB_31      0.0335286000
_diffrn_orient_matrix_UB_32      0.0049006000
_diffrn_orient_matrix_UB_33      0.0052782000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.632
_reflns_number_gt                4068
_reflns_number_total             4774
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4774
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.107
_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)+(0.0921P)²+5.6492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1789
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-C19
 1.39 with sigma of 0.01
 O3-C19 \\sim O2-C19
 with sigma of 0.02
3. Rigid bond restraints
 O3, C19, C23B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O3 \\sim C19 \\sim C23B: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004 within 2A
Uanis(C23B) \\sim Ueq: with sigma of 0.0006 and sigma for terminal atoms of
0.0012
Uanis(C19) = Uanis(O3) = Uanis(C23B)
Uanis(O2) = Uanis(C23) = Uanis(C16)
Uanis(C19) = Uanis(O2) = Uanis(C23)
5. Rigid body (RIGU) restrains
 O3, C19, C23B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O2, C19, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.003
6. Others
 Sof(O3)=Sof(C23B)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(O2)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
7.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C17(H17), C18(H18), C20(H20)
7.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C), C23B(H23D,H23E,H23F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.45181(6) 0.36124(7) 0.12649(11) 0.0406(3) Uani 1 1 d . . . . .
O2 O 0.5646(4) 0.1271(4) 0.6891(10) 0.0615(7) Uani 0.590(9) 1 d D . P A 1
O3 O 0.5671(6) 0.1268(5) 0.6272(14) 0.0615(7) Uani 0.410(9) 1 d D U P A 2
O1 O 0.39252(17) 0.41563(16) 0.5356(3) 0.0406(8) Uani 1 1 d . . . . .
N1 N 0.38658(17) 0.20795(18) 0.4002(4) 0.0350(9) Uani 1 1 d . . . . .
N3 N 0.46848(17) 0.32888(17) 0.3723(4) 0.0307(8) Uani 1 1 d . . . . .
H3 H 0.509942 0.336395 0.368949 0.037 Uiso 1 1 calc R U . . .
N2 N 0.45905(19) 0.3655(2) 0.6797(4) 0.0379(9) Uani 1 1 d . . . . .
C1 C 0.3275(2) 0.1759(2) 0.4022(4) 0.0324(9) Uani 1 1 d . . . . .
C2 C 0.3127(2) 0.1170(2) 0.3485(5) 0.0392(11) Uani 1 1 d . . . . .
H2 H 0.343898 0.093069 0.302265 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2505(3) 0.0940(2) 0.3645(5) 0.0431(12) Uani 1 1 d . . . . .
H3A H 0.239418 0.053696 0.328218 0.052 Uiso 1 1 calc R U . . .
C4 C 0.2055(2) 0.1270(2) 0.4298(5) 0.0401(11) Uani 1 1 d . . . . .
H4 H 0.163527 0.110125 0.439352 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2215(2) 0.1870(2) 0.4840(4) 0.0328(10) Uani 1 1 d . . . . .
H5 H 0.190269 0.211003 0.530001 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2822(2) 0.2103(2) 0.4698(4) 0.0286(9) Uani 1 1 d . . . . .
C7 C 0.3124(2) 0.2711(2) 0.5218(4) 0.0331(10) Uani 1 1 d . . . . .
C8 C 0.2664(2) 0.3284(3) 0.5111(6) 0.0475(13) Uani 1 1 d . . . . .
H8A H 0.249339 0.330753 0.423194 0.071 Uiso 1 1 calc R U . . .
H8B H 0.289537 0.367987 0.531090 0.071 Uiso 1 1 calc R U . . .
H8C H 0.230963 0.322887 0.572086 0.071 Uiso 1 1 calc R U . . .
C9 C 0.3305(3) 0.2594(3) 0.6638(5) 0.0510(14) Uani 1 1 d . . . . .
H9A H 0.346017 0.299439 0.702005 0.076 Uiso 1 1 calc R U . . .
H9B H 0.364313 0.226864 0.668439 0.076 Uiso 1 1 calc R U . . .
H9C H 0.292774 0.244444 0.711266 0.076 Uiso 1 1 calc R U . . .
C10 C 0.3734(2) 0.2758(2) 0.4328(4) 0.0285(9) Uani 1 1 d . . . . .
C11 C 0.3644(2) 0.3162(2) 0.3119(4) 0.0318(10) Uani 1 1 d . . . . .
H11A H 0.343187 0.290817 0.243445 0.038 Uiso 1 1 calc R U . . .
H11B H 0.337738 0.354302 0.330770 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4302(2) 0.3358(2) 0.2708(4) 0.0302(9) Uani 1 1 d . . . . .
C13 C 0.4360(2) 0.3077(2) 0.4903(4) 0.0294(9) Uani 1 1 d . . . . .
C14 C 0.4243(2) 0.3700(2) 0.5704(4) 0.0323(9) Uani 1 1 d . . . . .
C15 C 0.4787(2) 0.2697(2) 0.5816(5) 0.0381(9) Uani 1 1 d . . . . .
C16 C 0.4905(3) 0.3068(3) 0.6889(7) 0.0615(7) Uani 1 1 d . . . . .
C17 C 0.5274(3) 0.2858(3) 0.7903(6) 0.0553(13) Uani 1 1 d . . . . .
H17 H 0.534936 0.312414 0.863087 0.066 Uiso 1 1 calc R U . . .
C18 C 0.5525(3) 0.2265(3) 0.7833(7) 0.0635(15) Uani 1 1 d . . . . .
H18 H 0.577508 0.210878 0.852987 0.076 Uiso 1 1 calc R U . . .
C19 C 0.5426(3) 0.1874(3) 0.6754(7) 0.0615(7) Uani 1 1 d D U . . .
C20 C 0.5045(3) 0.2093(3) 0.5728(6) 0.0521(13) Uani 1 1 d . . . . .
H20 H 0.496853 0.183138 0.499468 0.063 Uiso 1 1 calc R U . . .
C21 C 0.4650(3) 0.4173(3) 0.7728(6) 0.0589(17) Uani 1 1 d . . . . .
H21A H 0.446019 0.404109 0.854958 0.088 Uiso 1 1 calc R U . . .
H21B H 0.442666 0.455358 0.740433 0.088 Uiso 1 1 calc R U . . .
H21C H 0.510444 0.427429 0.785697 0.088 Uiso 1 1 calc R U . . .
C22 C 0.4285(2) 0.1909(3) 0.2945(6) 0.0457(13) Uani 1 1 d . . . . .
H22A H 0.466472 0.218482 0.295879 0.068 Uiso 1 1 calc R U . . .
H22B H 0.405695 0.196663 0.212701 0.068 Uiso 1 1 calc R U . . .
H22C H 0.441605 0.146034 0.303261 0.068 Uiso 1 1 calc R U . . .
C23 C 0.5817(6) 0.0965(6) 0.7962(12) 0.0615(7) Uani 0.590(9) 1 d . . P A 1
H23A H 0.564745 0.119392 0.871306 0.092 Uiso 0.590(9) 1 calc R U P A 1
H23B H 0.628588 0.094837 0.801592 0.092 Uiso 0.590(9) 1 calc R U P A 1
H23C H 0.564507 0.052859 0.794622 0.092 Uiso 0.590(9) 1 calc R U P A 1
C23B C 0.6171(8) 0.0968(8) 0.6991(17) 0.0615(7) Uani 0.410(9) 1 d . U P A 2
H23D H 0.602581 0.054725 0.729225 0.092 Uiso 0.410(9) 1 calc R U P A 2
H23E H 0.628217 0.123572 0.773439 0.092 Uiso 0.410(9) 1 calc R U P A 2
H23F H 0.654914 0.091462 0.644088 0.092 Uiso 0.410(9) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.652(5) . ?
O2 C19 1.347(10) . ?
O2 C23 1.331(13) . ?
O3 C19 1.452(9) . ?
O3 C23B 1.429(19) . ?
O1 C14 1.215(6) . ?
N1 C1 1.403(6) . ?
N1 C10 1.483(5) . ?
N1 C22 1.447(6) . ?
N3 H3 0.8800 . ?
N3 C12 1.330(6) . ?
N3 C13 1.469(6) . ?
N2 C14 1.350(6) . ?
N2 C16 1.393(8) . ?
N2 C21 1.456(6) . ?
C1 C2 1.384(6) . ?
C1 C6 1.378(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(7) . ?
C3 H3A 0.9500 . ?
C3 C4 1.347(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.413(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.365(6) . ?
C6 C7 1.514(6) . ?
C7 C8 1.537(7) . ?
C7 C9 1.541(7) . ?
C7 C10 1.577(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.522(6) . ?
C10 C13 1.582(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.495(6) . ?
C13 C14 1.563(6) . ?
C13 C15 1.523(6) . ?
C15 C16 1.378(9) . ?
C15 C20 1.374(7) . ?
C16 C17 1.376(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.346(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.401(10) . ?
C19 C20 1.405(9) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O2 C19 128.9(10) . . ?
C23B O3 C19 117.4(12) . . ?
C1 N1 C10 106.8(3) . . ?
C1 N1 C22 115.2(4) . . ?
C22 N1 C10 121.3(4) . . ?
C12 N3 H3 122.7 . . ?
C12 N3 C13 114.5(3) . . ?
C13 N3 H3 122.7 . . ?
C14 N2 C16 111.8(4) . . ?
C14 N2 C21 123.5(5) . . ?
C16 N2 C21 124.6(5) . . ?
C2 C1 N1 127.8(4) . . ?
C6 C1 N1 111.2(4) . . ?
C6 C1 C2 121.0(4) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.7(4) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 C2 122.2(5) . . ?
C4 C3 H3A 118.9 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 109.5(4) . . ?
C5 C6 C1 120.4(4) . . ?
C5 C6 C7 130.1(4) . . ?
C6 C7 C8 111.5(4) . . ?
C6 C7 C9 108.1(4) . . ?
C6 C7 C10 100.4(3) . . ?
C8 C7 C9 110.2(4) . . ?
C8 C7 C10 114.4(4) . . ?
C9 C7 C10 111.8(4) . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C7 102.9(3) . . ?
N1 C10 C11 111.3(4) . . ?
N1 C10 C13 109.5(3) . . ?
C7 C10 C13 118.2(3) . . ?
C11 C10 C7 114.7(4) . . ?
C11 C10 C13 100.5(3) . . ?
C10 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C12 C11 C10 105.8(4) . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
N3 C12 S1 126.0(4) . . ?
N3 C12 C11 107.2(4) . . ?
C11 C12 S1 126.7(3) . . ?
N3 C13 C10 101.1(3) . . ?
N3 C13 C14 105.3(3) . . ?
N3 C13 C15 113.9(4) . . ?
C14 C13 C10 115.0(3) . . ?
C15 C13 C10 120.0(4) . . ?
C15 C13 C14 101.2(4) . . ?
O1 C14 N2 126.7(4) . . ?
O1 C14 C13 125.4(4) . . ?
N2 C14 C13 107.7(4) . . ?
C16 C15 C13 108.4(4) . . ?
C20 C15 C13 131.7(5) . . ?
C20 C15 C16 119.9(5) . . ?
C15 C16 N2 110.8(5) . . ?
C17 C16 N2 126.6(6) . . ?
C17 C16 C15 122.6(6) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 C16 118.0(6) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.5(6) . . ?
C19 C18 H18 119.3 . . ?
O2 C19 C18 114.2(7) . . ?
O2 C19 C20 125.2(7) . . ?
C18 C19 O3 136.9(8) . . ?
C18 C19 C20 120.0(6) . . ?
C20 C19 O3 102.8(7) . . ?
C15 C20 C19 118.0(6) . . ?
C15 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C23B H23D 109.5 . . ?
O3 C23B H23E 109.5 . . ?
O3 C23B H23F 109.5 . . ?
H23D C23B H23E 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C19 C20 C15 171.2(7) . . . . ?
O3 C19 C20 C15 -173.6(7) . . . . ?
N1 C1 C2 C3 179.0(5) . . . . ?
N1 C1 C6 C5 -179.4(4) . . . . ?
N1 C1 C6 C7 -1.2(5) . . . . ?
N1 C10 C11 C12 -85.4(4) . . . . ?
N1 C10 C13 N3 86.7(4) . . . . ?
N1 C10 C13 C14 -160.4(4) . . . . ?
N1 C10 C13 C15 -39.4(5) . . . . ?
N3 C13 C14 O1 60.7(5) . . . . ?
N3 C13 C14 N2 -115.4(4) . . . . ?
N3 C13 C15 C16 109.9(5) . . . . ?
N3 C13 C15 C20 -70.4(6) . . . . ?
N2 C16 C17 C18 178.1(6) . . . . ?
C1 N1 C10 C7 29.3(4) . . . . ?
C1 N1 C10 C11 -94.0(4) . . . . ?
C1 N1 C10 C13 155.8(4) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
C1 C6 C7 C8 140.2(4) . . . . ?
C1 C6 C7 C9 -98.5(5) . . . . ?
C1 C6 C7 C10 18.7(5) . . . . ?
C2 C1 C6 C5 -0.6(7) . . . . ?
C2 C1 C6 C7 177.7(4) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C4 C5 C6 C7 -177.3(4) . . . . ?
C5 C6 C7 C8 -41.7(7) . . . . ?
C5 C6 C7 C9 79.5(6) . . . . ?
C5 C6 C7 C10 -163.3(5) . . . . ?
C6 C1 C2 C3 0.4(7) . . . . ?
C6 C7 C10 N1 -28.3(4) . . . . ?
C6 C7 C10 C11 92.7(4) . . . . ?
C6 C7 C10 C13 -149.1(4) . . . . ?
C7 C10 C11 C12 158.4(4) . . . . ?
C7 C10 C13 N3 -156.0(4) . . . . ?
C7 C10 C13 C14 -43.1(5) . . . . ?
C7 C10 C13 C15 77.9(5) . . . . ?
C8 C7 C10 N1 -147.7(4) . . . . ?
C8 C7 C10 C11 -26.7(5) . . . . ?
C8 C7 C10 C13 91.5(5) . . . . ?
C9 C7 C10 N1 86.1(5) . . . . ?
C9 C7 C10 C11 -152.9(4) . . . . ?
C9 C7 C10 C13 -34.7(6) . . . . ?
C10 N1 C1 C2 162.6(5) . . . . ?
C10 N1 C1 C6 -18.6(5) . . . . ?
C10 C11 C12 S1 160.7(3) . . . . ?
C10 C11 C12 N3 -19.2(5) . . . . ?
C10 C13 C14 O1 -49.7(6) . . . . ?
C10 C13 C14 N2 134.3(4) . . . . ?
C10 C13 C15 C16 -130.2(5) . . . . ?
C10 C13 C15 C20 49.6(7) . . . . ?
C11 C10 C13 N3 -30.5(4) . . . . ?
C11 C10 C13 C14 82.4(4) . . . . ?
C11 C10 C13 C15 -156.6(4) . . . . ?
C12 N3 C13 C10 21.7(5) . . . . ?
C12 N3 C13 C14 -98.3(4) . . . . ?
C12 N3 C13 C15 151.8(4) . . . . ?
C13 N3 C12 S1 177.8(3) . . . . ?
C13 N3 C12 C11 -2.4(5) . . . . ?
C13 C10 C11 C12 30.6(4) . . . . ?
C13 C15 C16 N2 0.9(7) . . . . ?
C13 C15 C16 C17 179.5(6) . . . . ?
C13 C15 C20 C19 -179.8(5) . . . . ?
C14 N2 C16 C15 1.5(7) . . . . ?
C14 N2 C16 C17 -177.0(6) . . . . ?
C14 C13 C15 C16 -2.6(5) . . . . ?
C14 C13 C15 C20 177.2(5) . . . . ?
C15 C13 C14 O1 179.5(4) . . . . ?
C15 C13 C14 N2 3.5(4) . . . . ?
C15 C16 C17 C18 -0.3(10) . . . . ?
C16 N2 C14 O1 -179.2(5) . . . . ?
C16 N2 C14 C13 -3.2(6) . . . . ?
C16 C15 C20 C19 0.0(9) . . . . ?
C16 C17 C18 C19 1.1(10) . . . . ?
C17 C18 C19 O2 -172.8(7) . . . . ?
C17 C18 C19 O3 170.6(10) . . . . ?
C17 C18 C19 C20 -1.5(11) . . . . ?
C18 C19 C20 C15 0.9(9) . . . . ?
C20 C15 C16 N2 -178.9(5) . . . . ?
C20 C15 C16 C17 -0.3(10) . . . . ?
C21 N2 C14 O1 -2.0(8) . . . . ?
C21 N2 C14 C13 174.0(5) . . . . ?
C21 N2 C16 C15 -175.6(5) . . . . ?
C21 N2 C16 C17 5.8(10) . . . . ?
C22 N1 C1 C2 24.7(7) . . . . ?
C22 N1 C1 C6 -156.5(4) . . . . ?
C22 N1 C10 C7 164.0(4) . . . . ?
C22 N1 C10 C11 40.8(6) . . . . ?
C22 N1 C10 C13 -69.4(5) . . . . ?
C23 O2 C19 C18 15.3(14) . . . . ?
C23 O2 C19 C20 -155.6(10) . . . . ?
C23B O3 C19 C18 -3.9(19) . . . . ?
C23B O3 C19 C20 169.1(12) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 15.7 0.0 ?
2 0.000 0.000 0.500 9.4 0.8 ?
3 0.000 0.500 0.750 260.6 40.4 ?
4 0.500 1.000 0.250 260.6 40.4 ?
5 0.500 0.500 0.500 15.7 0.0 ?
6 0.500 0.500 0.000 9.4 0.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2022-10-08
_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 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.786
####################################################################### 
# 
# 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_b10
_database_code_depnum_ccdc_archive 'CCDC 2232176'
loop_
_audit_author_name
_audit_author_address
fddf
;df
China
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N3 O S'
_chemical_formula_sum            'C23 H25 N3 O S'
_chemical_formula_weight         391.52
_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                   18.8625(12)
_cell_length_b                   8.7470(7)
_cell_length_c                   25.549(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.552(6)
_cell_angle_gamma                90
_cell_volume                     4207.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4351
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.1320
_cell_measurement_theta_min      2.5700
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11218
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.164
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  60.00   1.00    2.00    --  -11.27  57.00  90.00   99
  2  ω     43.00  69.00   1.00    2.00    --   11.90 178.00  90.00   26
  3  ω    -17.00  75.00   1.00    2.00    --   11.90  77.00-150.00   92
  4  ω    -79.00 -51.00   1.00    2.00    --  -11.27 -57.00 -60.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0329818500
_diffrn_orient_matrix_UB_12      -0.0294217500
_diffrn_orient_matrix_UB_13      0.0073327000
_diffrn_orient_matrix_UB_21      -0.0170883500
_diffrn_orient_matrix_UB_22      0.0317132500
_diffrn_orient_matrix_UB_23      -0.0230225000
_diffrn_orient_matrix_UB_31      0.0063040000
_diffrn_orient_matrix_UB_32      -0.0685399000
_diffrn_orient_matrix_UB_33      -0.0137721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3137
_reflns_number_total             3688
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.033
_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)+(0.0409P)²+3.4865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0971
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.58489(2) 0.41580(6) 0.69089(2) 0.03063(15) Uani 1 1 d . . . . .
O1 O 0.41508(6) 0.72907(14) 0.63007(5) 0.0318(3) Uani 1 1 d . . . . .
N1 N 0.39780(7) 0.21938(16) 0.59558(6) 0.0229(3) Uani 1 1 d . . . . .
N2 N 0.44362(7) 0.43933(15) 0.68328(6) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.440880 0.434133 0.717496 0.024 Uiso 1 1 calc R U . . .
N3 N 0.30525(7) 0.67222(16) 0.65831(6) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.38551(8) 0.2946(2) 0.50898(7) 0.0250(4) Uani 1 1 d . . . . .
C2 C 0.38410(9) 0.2727(2) 0.45545(8) 0.0334(5) Uani 1 1 d . . . . .
H2A H 0.375372 0.356239 0.432181 0.040 Uiso 1 1 calc R U . . .
C3 C 0.39559(10) 0.1270(3) 0.43592(8) 0.0399(5) Uani 1 1 d . . . . .
H3 H 0.395222 0.110809 0.399132 0.048 Uiso 1 1 calc R U . . .
C4 C 0.40751(10) 0.0061(3) 0.46989(9) 0.0396(5) Uani 1 1 d . . . . .
H4 H 0.414417 -0.093186 0.456012 0.048 Uiso 1 1 calc R U . . .
C5 C 0.40969(9) 0.0256(2) 0.52394(8) 0.0323(5) Uani 1 1 d . . . . .
H5 H 0.418517 -0.058157 0.547083 0.039 Uiso 1 1 calc R U . . .
C6 C 0.39853(8) 0.1718(2) 0.54297(7) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.40812(8) 0.38805(19) 0.59526(7) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.37039(9) 0.4354(2) 0.54108(7) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.28904(9) 0.4449(2) 0.54396(8) 0.0307(4) Uani 1 1 d . . . . .
H9A H 0.271833 0.352128 0.560577 0.046 Uiso 1 1 calc R U . . .
H9B H 0.266629 0.454045 0.508462 0.046 Uiso 1 1 calc R U . . .
H9C H 0.276988 0.534398 0.564689 0.046 Uiso 1 1 calc R U . . .
C10 C 0.39702(10) 0.5820(2) 0.51655(8) 0.0332(5) Uani 1 1 d . . . . .
H10A H 0.386949 0.669236 0.538994 0.050 Uiso 1 1 calc R U . . .
H10B H 0.372855 0.596428 0.481831 0.050 Uiso 1 1 calc R U . . .
H10C H 0.448352 0.574538 0.513077 0.050 Uiso 1 1 calc R U . . .
C12 C 0.48815(8) 0.4281(2) 0.60212(7) 0.0218(4) Uani 1 1 d . . . . .
H12A H 0.517142 0.350667 0.584946 0.026 Uiso 1 1 calc R U . . .
H12B H 0.497576 0.529764 0.586999 0.026 Uiso 1 1 calc R U . . .
C13 C 0.50432(9) 0.42821(18) 0.66038(7) 0.0216(4) Uani 1 1 d . . . . .
C14 C 0.38098(8) 0.46114(19) 0.64676(7) 0.0201(4) Uani 1 1 d . . . . .
C15 C 0.37058(9) 0.63731(19) 0.64263(7) 0.0215(4) Uani 1 1 d . . . . .
C16 C 0.31145(8) 0.41101(19) 0.66764(7) 0.0209(4) Uani 1 1 d . . . . .
C17 C 0.28576(10) 0.2694(2) 0.68061(7) 0.0290(4) Uani 1 1 d . . . . .
H17 H 0.314087 0.180415 0.677536 0.035 Uiso 1 1 calc R U . . .
C18 C 0.21740(10) 0.2589(2) 0.69833(8) 0.0361(5) Uani 1 1 d . . . . .
H18 H 0.199002 0.161901 0.707272 0.043 Uiso 1 1 calc R U . . .
C19 C 0.17641(10) 0.3877(3) 0.70298(8) 0.0377(5) Uani 1 1 d . . . . .
H19 H 0.130028 0.378023 0.715120 0.045 Uiso 1 1 calc R U . . .
C20 C 0.20128(9) 0.5313(2) 0.69034(7) 0.0325(5) Uani 1 1 d . . . . .
H20 H 0.173006 0.620312 0.693496 0.039 Uiso 1 1 calc R U . . .
C21 C 0.26907(9) 0.5391(2) 0.67293(7) 0.0224(4) Uani 1 1 d . . . . .
C22 C 0.27785(10) 0.8285(2) 0.65854(8) 0.0315(4) Uani 1 1 d . . . . .
H22A H 0.317254 0.899571 0.668435 0.038 Uiso 1 1 calc R U . . .
H22B H 0.242247 0.836980 0.685284 0.038 Uiso 1 1 calc R U . . .
C23 C 0.24404(12) 0.8747(3) 0.60583(9) 0.0483(6) Uani 1 1 d . . . . .
H23A H 0.279450 0.869192 0.579399 0.072 Uiso 1 1 calc R U . . .
H23B H 0.226108 0.979570 0.607789 0.072 Uiso 1 1 calc R U . . .
H23C H 0.204597 0.805367 0.596069 0.072 Uiso 1 1 calc R U . . .
C24 C 0.43830(10) 0.1228(2) 0.63366(7) 0.0293(4) Uani 1 1 d . . . . .
H24A H 0.489071 0.130935 0.627975 0.044 Uiso 1 1 calc R U . . .
H24B H 0.423102 0.016202 0.629149 0.044 Uiso 1 1 calc R U . . .
H24C H 0.429799 0.156654 0.669291 0.044 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 C13 1.6680(17) . ?
O1 C15 1.219(2) . ?
N1 C6 1.408(2) . ?
N1 C7 1.488(2) . ?
N1 C24 1.467(2) . ?
N2 H2 0.8800 . ?
N2 C13 1.321(2) . ?
N2 C14 1.472(2) . ?
N3 C15 1.354(2) . ?
N3 C21 1.412(2) . ?
N3 C22 1.461(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.393(3) . ?
C1 C8 1.517(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C7 C8 1.572(2) . ?
C7 C12 1.549(2) . ?
C7 C14 1.576(2) . ?
C8 C9 1.543(2) . ?
C8 C10 1.526(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.501(2) . ?
C14 C15 1.556(2) . ?
C14 C16 1.511(2) . ?
C16 C17 1.378(2) . ?
C16 C21 1.388(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.396(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.376(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.509(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C7 106.19(13) . . ?
C6 N1 C24 115.30(14) . . ?
C24 N1 C7 120.78(14) . . ?
C13 N2 H2 122.8 . . ?
C13 N2 C14 114.35(14) . . ?
C14 N2 H2 122.8 . . ?
C15 N3 C21 110.85(14) . . ?
C15 N3 C22 122.74(14) . . ?
C21 N3 C22 126.41(14) . . ?
C2 C1 C6 120.17(18) . . ?
C2 C1 C8 131.00(17) . . ?
C6 C1 C8 108.72(15) . . ?
C1 C2 H2A 120.4 . . ?
C1 C2 C3 119.29(19) . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.02(19) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.7(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.75(19) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 N1 110.81(15) . . ?
C5 C6 N1 128.11(17) . . ?
C5 C6 C1 121.08(17) . . ?
N1 C7 C8 102.34(13) . . ?
N1 C7 C12 110.52(13) . . ?
N1 C7 C14 110.37(13) . . ?
C8 C7 C14 118.38(13) . . ?
C12 C7 C8 115.14(13) . . ?
C12 C7 C14 100.28(13) . . ?
C1 C8 C7 99.91(13) . . ?
C1 C8 C9 106.88(14) . . ?
C1 C8 C10 112.51(15) . . ?
C9 C8 C7 111.67(14) . . ?
C10 C8 C7 116.13(14) . . ?
C10 C8 C9 109.16(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C12 H12A 110.9 . . ?
C7 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C13 C12 C7 104.42(13) . . ?
C13 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
N2 C13 S1 125.96(14) . . ?
N2 C13 C12 108.12(14) . . ?
C12 C13 S1 125.92(12) . . ?
N2 C14 C7 100.79(12) . . ?
N2 C14 C15 105.32(13) . . ?
N2 C14 C16 114.76(14) . . ?
C15 C14 C7 113.02(13) . . ?
C16 C14 C7 120.71(14) . . ?
C16 C14 C15 101.70(13) . . ?
O1 C15 N3 125.72(16) . . ?
O1 C15 C14 125.73(15) . . ?
N3 C15 C14 108.45(14) . . ?
C17 C16 C14 132.18(16) . . ?
C17 C16 C21 119.27(15) . . ?
C21 C16 C14 108.54(14) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.86(18) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.64(18) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.46(17) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 121.5 . . ?
C21 C20 C19 116.94(18) . . ?
C21 C20 H20 121.5 . . ?
C16 C21 N3 110.45(14) . . ?
C20 C21 N3 126.72(16) . . ?
C20 C21 C16 122.83(17) . . ?
N3 C22 H22A 109.2 . . ?
N3 C22 H22B 109.2 . . ?
N3 C22 C23 112.15(16) . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 C7 C8 C1 -32.68(15) . . . . ?
N1 C7 C8 C9 80.05(16) . . . . ?
N1 C7 C8 C10 -153.92(14) . . . . ?
N1 C7 C12 C13 -85.35(16) . . . . ?
N1 C7 C14 N2 83.96(14) . . . . ?
N1 C7 C14 C15 -164.13(13) . . . . ?
N1 C7 C14 C16 -43.6(2) . . . . ?
N2 C14 C15 O1 55.7(2) . . . . ?
N2 C14 C15 N3 -120.74(14) . . . . ?
N2 C14 C16 C17 -66.4(2) . . . . ?
N2 C14 C16 C21 114.31(16) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C1 C6 N1 179.84(14) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C8 C7 -161.06(17) . . . . ?
C2 C1 C8 C9 82.5(2) . . . . ?
C2 C1 C8 C10 -37.3(2) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 N1 179.61(16) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C6 N1 C7 C8 32.46(16) . . . . ?
C6 N1 C7 C12 -90.64(15) . . . . ?
C6 N1 C7 C14 159.35(13) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C1 C8 C7 22.87(17) . . . . ?
C6 C1 C8 C9 -93.53(17) . . . . ?
C6 C1 C8 C10 146.67(15) . . . . ?
C7 N1 C6 C1 -19.04(18) . . . . ?
C7 N1 C6 C5 161.38(17) . . . . ?
C7 C12 C13 S1 161.87(12) . . . . ?
C7 C12 C13 N2 -17.93(17) . . . . ?
C7 C14 C15 O1 -53.4(2) . . . . ?
C7 C14 C15 N3 130.16(15) . . . . ?
C7 C14 C16 C17 54.5(3) . . . . ?
C7 C14 C16 C21 -124.79(16) . . . . ?
C8 C1 C2 C3 -175.51(17) . . . . ?
C8 C1 C6 N1 -3.59(19) . . . . ?
C8 C1 C6 C5 176.02(15) . . . . ?
C8 C7 C12 C13 159.33(14) . . . . ?
C8 C7 C14 N2 -158.67(13) . . . . ?
C8 C7 C14 C15 -46.76(19) . . . . ?
C8 C7 C14 C16 73.8(2) . . . . ?
C12 C7 C8 C1 87.25(16) . . . . ?
C12 C7 C8 C9 -160.02(15) . . . . ?
C12 C7 C8 C10 -34.0(2) . . . . ?
C12 C7 C14 N2 -32.61(14) . . . . ?
C12 C7 C14 C15 79.30(15) . . . . ?
C12 C7 C14 C16 -160.13(14) . . . . ?
C13 N2 C14 C7 24.90(17) . . . . ?
C13 N2 C14 C15 -92.80(16) . . . . ?
C13 N2 C14 C16 156.23(14) . . . . ?
C14 N2 C13 S1 175.28(12) . . . . ?
C14 N2 C13 C12 -4.92(19) . . . . ?
C14 C7 C8 C1 -154.23(14) . . . . ?
C14 C7 C8 C9 -41.5(2) . . . . ?
C14 C7 C8 C10 84.53(19) . . . . ?
C14 C7 C12 C13 31.11(15) . . . . ?
C14 C16 C17 C18 -178.75(18) . . . . ?
C14 C16 C21 N3 -1.27(19) . . . . ?
C14 C16 C21 C20 178.82(16) . . . . ?
C15 N3 C21 C16 0.8(2) . . . . ?
C15 N3 C21 C20 -179.31(17) . . . . ?
C15 N3 C22 C23 85.2(2) . . . . ?
C15 C14 C16 C17 -179.48(19) . . . . ?
C15 C14 C16 C21 1.19(18) . . . . ?
C16 C14 C15 O1 175.73(17) . . . . ?
C16 C14 C15 N3 -0.73(18) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C16 C21 N3 179.30(16) . . . . ?
C17 C16 C21 C20 -0.6(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 N3 -179.52(17) . . . . ?
C19 C20 C21 C16 0.4(3) . . . . ?
C21 N3 C15 O1 -176.44(17) . . . . ?
C21 N3 C15 C14 0.03(19) . . . . ?
C21 N3 C22 C23 -93.8(2) . . . . ?
C21 C16 C17 C18 0.5(3) . . . . ?
C22 N3 C15 O1 4.5(3) . . . . ?
C22 N3 C15 C14 -179.08(15) . . . . ?
C22 N3 C21 C16 179.86(16) . . . . ?
C22 N3 C21 C20 -0.2(3) . . . . ?
C24 N1 C6 C1 -155.64(14) . . . . ?
C24 N1 C6 C5 24.8(2) . . . . ?
C24 N1 C7 C8 166.16(14) . . . . ?
C24 N1 C7 C12 43.1(2) . . . . ?
C24 N1 C7 C14 -66.95(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.411 0.750 69.4 17.9 ?
2 0.000 0.589 0.250 69.4 17.9 ?
3 0.500 -0.089 0.750 69.4 17.9 ?
4 0.500 0.089 0.250 69.4 17.9 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2022-10-08
_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 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.791
####################################################################### 
# 
# 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_d151
_database_code_depnum_ccdc_archive 'CCDC 2232177'
loop_
_audit_author_name
_audit_author_address
fgfg
;eerfg
China
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H25 N2 O S'
_chemical_formula_sum            'C24 H25 N2 O S'
_chemical_formula_weight         389.52
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4539(5)
_cell_length_b                   9.8480(6)
_cell_length_c                   14.0220(9)
_cell_angle_alpha                78.299(5)
_cell_angle_beta                 84.219(5)
_cell_angle_gamma                85.023(5)
_cell_volume                     1000.46(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3576
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4720
_cell_measurement_theta_min      3.1960
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    1.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6641
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.657
_diffrn_reflns_theta_min         3.230
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     14.00 114.00   1.00    1.00    --   40.73  57.00 -60.00  100
  2  ω     92.00 177.00   1.00    1.00    --  106.95  30.00 -30.00   85
  3  ω    143.00 178.00   1.00    1.00    --  106.95  15.00 -90.00   35
  4  ω    109.00 161.00   1.00    1.00    --  106.95 125.00 -90.00   52
  5  ω     90.00 117.00   1.00    1.00    --  106.95  15.00 -90.00   27
  6  ω     61.00  89.00   1.00    1.00    --  106.95  15.00 -90.00   28
  7  ω     40.00 135.00   1.00    1.00    --  106.95 -61.00-120.00   95
  8  ω     83.00 113.00   1.00    1.00    --  106.95-125.00-180.00   30
  9  ω     41.00  68.00   1.00    1.00    --  106.95-125.00-180.00   27
 10  ω     28.00 109.00   1.00    1.00    --  106.95 -95.00-150.00   81
 11  ω     32.00 140.00   1.00    1.00    --  106.95 -77.00   0.00  108
 12  ω     80.00 120.00   1.00    1.00    --  106.95-125.00  30.00   40
 13  ω     56.00 118.00   1.00    1.00    --  106.95 -30.00 150.00   62
 14  ω     32.00 133.00   1.00    1.00    --  106.95 -30.00 -30.00  101
 15  ω    -64.00  22.00   1.00    1.00    --  -40.73  57.00  90.00   86
 16  ω    -64.00  35.00   1.00    1.00    --  -40.73  77.00-180.00   99
 17  ω    -82.00 -38.00   1.00    1.00    --  -40.73 125.00 -30.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1451477000
_diffrn_orient_matrix_UB_12      0.0492890000
_diffrn_orient_matrix_UB_13      -0.0831618000
_diffrn_orient_matrix_UB_21      -0.0895487000
_diffrn_orient_matrix_UB_22      0.1488079000
_diffrn_orient_matrix_UB_23      -0.0126116000
_diffrn_orient_matrix_UB_31      0.1194471000
_diffrn_orient_matrix_UB_32      0.0326610000
_diffrn_orient_matrix_UB_33      0.0748711000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3371
_reflns_number_total             3903
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.056
_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)+(0.0709P)²+0.9513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1523
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C12, C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.01517(8) 0.26469(6) 0.06857(4) 0.02814(18) Uani 1 1 d . . . . .
O1 O -0.1274(3) 0.5611(2) 0.28121(15) 0.0406(5) Uani 1 1 d . . . . .
N1 N 0.4356(3) 0.35403(19) 0.23281(13) 0.0226(4) Uani 1 1 d . . . . .
N2 N 0.1165(3) 0.4816(2) 0.11849(14) 0.0270(4) Uani 1 1 d . . . . .
H2 H 0.108389 0.532407 0.059538 0.032 Uiso 1 1 calc R U . . .
C1 C 0.4208(3) 0.2947(2) 0.40043(16) 0.0225(5) Uani 1 1 d . . . . .
C2 C 0.4807(3) 0.2304(2) 0.48909(17) 0.0261(5) Uani 1 1 d . . . . .
H2A H 0.414996 0.246580 0.547849 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6380(3) 0.1413(2) 0.49349(18) 0.0275(5) Uani 1 1 d . . . . .
C4 C 0.7285(3) 0.1189(2) 0.40570(19) 0.0292(5) Uani 1 1 d . . . . .
H4 H 0.834048 0.057296 0.407605 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6702(3) 0.1836(2) 0.31483(18) 0.0274(5) Uani 1 1 d . . . . .
H5 H 0.733983 0.166537 0.255817 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5163(3) 0.2733(2) 0.31353(16) 0.0229(5) Uani 1 1 d . . . . .
C7 C 0.2602(3) 0.3975(2) 0.37780(16) 0.0236(5) Uani 1 1 d . . . . .
C8 C 0.2480(3) 0.3959(2) 0.26664(16) 0.0230(5) Uani 1 1 d . . . . .
C9 C 0.1812(3) 0.5351(2) 0.19937(17) 0.0252(5) Uani 1 1 d . . . . .
C10 C 0.1142(3) 0.2955(2) 0.24579(16) 0.0246(5) Uani 1 1 d . . . . .
H10A H 0.170344 0.199500 0.253024 0.030 Uiso 1 1 calc R U . . .
H10B H 0.003101 0.295433 0.290921 0.030 Uiso 1 1 calc R U . . .
C11 C 0.0721(3) 0.3515(2) 0.14204(17) 0.0248(5) Uani 1 1 d . . . . .
C12 C 0.0102(3) 0.6130(3) 0.24194(18) 0.0301(5) Uani 1 1 d . . . . .
C13 C 0.0376(3) 0.7515(2) 0.22042(17) 0.0252(5) Uani 1 1 d . . . . .
C14 C 0.2130(4) 0.7760(3) 0.17687(18) 0.0311(5) Uani 1 1 d . . . . .
C15 C 0.3070(4) 0.6510(2) 0.16387(17) 0.0281(5) Uani 1 1 d . . . . .
C16 C 0.4847(4) 0.6523(3) 0.12581(18) 0.0326(6) Uani 1 1 d . . . . .
H16 H 0.551590 0.568444 0.117252 0.039 Uiso 1 1 calc R U . . .
C17 C 0.5652(4) 0.7799(3) 0.0999(2) 0.0413(7) Uani 1 1 d . . . . .
H17 H 0.687615 0.782378 0.073493 0.050 Uiso 1 1 calc R U . . .
C18 C 0.4682(5) 0.9013(3) 0.1124(2) 0.0448(7) Uani 1 1 d . . . . .
H18 H 0.525435 0.986465 0.094599 0.054 Uiso 1 1 calc R U . . .
C19 C 0.2901(5) 0.9026(3) 0.1500(2) 0.0419(7) Uani 1 1 d . . . . .
H19 H 0.222976 0.986908 0.157298 0.050 Uiso 1 1 calc R U . . .
C20 C -0.0951(5) 0.8583(3) 0.2451(2) 0.0485(8) Uani 1 1 d . . . . .
H20A H -0.055687 0.895799 0.298625 0.073 Uiso 1 1 calc R U . . .
H20B H -0.211941 0.818161 0.265661 0.073 Uiso 1 1 calc R U . . .
H20C H -0.107455 0.933208 0.187855 0.073 Uiso 1 1 calc R U . . .
C21 C 0.3099(4) 0.5389(2) 0.39385(18) 0.0294(5) Uani 1 1 d . . . . .
H21A H 0.331552 0.531620 0.462557 0.044 Uiso 1 1 calc R U . . .
H21B H 0.210449 0.608826 0.377007 0.044 Uiso 1 1 calc R U . . .
H21C H 0.419572 0.566518 0.352224 0.044 Uiso 1 1 calc R U . . .
C22 C 0.0921(3) 0.3509(3) 0.44465(18) 0.0302(5) Uani 1 1 d . . . . .
H22A H 0.073136 0.254583 0.441966 0.045 Uiso 1 1 calc R U . . .
H22B H -0.013603 0.411132 0.422814 0.045 Uiso 1 1 calc R U . . .
H22C H 0.109355 0.357243 0.511948 0.045 Uiso 1 1 calc R U . . .
C23 C 0.7051(4) 0.0701(3) 0.59001(19) 0.0357(6) Uani 1 1 d . . . . .
H23A H 0.719286 0.139780 0.629181 0.054 Uiso 1 1 calc R U . . .
H23B H 0.821871 0.019558 0.578710 0.054 Uiso 1 1 calc R U . . .
H23C H 0.617658 0.004736 0.625024 0.054 Uiso 1 1 calc R U . . .
C24 C 0.4763(3) 0.3090(3) 0.13974(17) 0.0294(5) Uani 1 1 d . . . . .
H24A H 0.607311 0.291588 0.127810 0.044 Uiso 1 1 calc R U . . .
H24B H 0.432270 0.381764 0.087042 0.044 Uiso 1 1 calc R U . . .
H24C H 0.416804 0.223451 0.141776 0.044 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 C11 1.674(2) . ?
O1 C12 1.216(3) . ?
N1 C6 1.401(3) . ?
N1 C8 1.482(3) . ?
N1 C24 1.457(3) . ?
N2 H2 0.8800 . ?
N2 C9 1.481(3) . ?
N2 C11 1.319(3) . ?
C1 C2 1.374(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.515(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.401(3) . ?
C3 C4 1.391(4) . ?
C3 C23 1.504(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C7 C8 1.574(3) . ?
C7 C21 1.537(3) . ?
C7 C22 1.532(3) . ?
C8 C9 1.572(3) . ?
C8 C10 1.551(3) . ?
C9 C12 1.559(3) . ?
C9 C15 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.502(3) . ?
C12 C13 1.365(3) . ?
C13 C14 1.405(4) . ?
C13 C20 1.451(3) . ?
C14 C15 1.398(3) . ?
C14 C19 1.384(4) . ?
C15 C16 1.377(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.404(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(5) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C8 107.56(17) . . ?
C6 N1 C24 116.84(19) . . ?
C24 N1 C8 121.09(18) . . ?
C9 N2 H2 122.7 . . ?
C11 N2 H2 122.7 . . ?
C11 N2 C9 114.51(19) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 C7 129.8(2) . . ?
C6 C1 C7 109.56(19) . . ?
C1 C2 H2A 119.7 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C23 121.1(2) . . ?
C4 C3 C2 117.8(2) . . ?
C4 C3 C23 121.1(2) . . ?
C3 C4 H4 118.7 . . ?
C3 C4 C5 122.5(2) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 N1 110.67(19) . . ?
C5 C6 N1 128.7(2) . . ?
C5 C6 C1 120.6(2) . . ?
C1 C7 C8 100.95(17) . . ?
C1 C7 C21 107.49(19) . . ?
C1 C7 C22 110.81(19) . . ?
C21 C7 C8 112.35(19) . . ?
C22 C7 C8 114.62(19) . . ?
C22 C7 C21 110.08(19) . . ?
N1 C8 C7 103.30(17) . . ?
N1 C8 C9 109.88(18) . . ?
N1 C8 C10 110.57(18) . . ?
C9 C8 C7 117.43(18) . . ?
C10 C8 C7 115.33(18) . . ?
C10 C8 C9 100.46(17) . . ?
N2 C9 C8 100.90(17) . . ?
N2 C9 C12 104.15(18) . . ?
N2 C9 C15 112.90(19) . . ?
C12 C9 C8 115.33(19) . . ?
C15 C9 C8 120.5(2) . . ?
C15 C9 C12 102.25(19) . . ?
C8 C10 H10A 110.8 . . ?
C8 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
C11 C10 C8 104.57(18) . . ?
C11 C10 H10A 110.8 . . ?
C11 C10 H10B 110.8 . . ?
N2 C11 S1 125.75(18) . . ?
N2 C11 C10 107.98(19) . . ?
C10 C11 S1 126.27(17) . . ?
O1 C12 C9 126.3(2) . . ?
O1 C12 C13 126.1(2) . . ?
C13 C12 C9 107.4(2) . . ?
C12 C13 C14 111.6(2) . . ?
C12 C13 C20 123.7(3) . . ?
C14 C13 C20 124.6(2) . . ?
C15 C14 C13 110.3(2) . . ?
C19 C14 C13 127.3(2) . . ?
C19 C14 C15 122.4(3) . . ?
C14 C15 C9 108.1(2) . . ?
C16 C15 C9 132.7(2) . . ?
C16 C15 C14 119.2(2) . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.8(3) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 H19 121.3 . . ?
C18 C19 C14 117.3(3) . . ?
C18 C19 H19 121.3 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 C21 H21A 109.5 . . ?
C7 C21 H21B 109.5 . . ?
C7 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 C22 H22A 109.5 . . ?
C7 C22 H22B 109.5 . . ?
C7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C12 C13 C14 178.8(2) . . . . ?
O1 C12 C13 C20 2.2(4) . . . . ?
N1 C8 C9 N2 84.8(2) . . . . ?
N1 C8 C9 C12 -163.71(18) . . . . ?
N1 C8 C9 C15 -40.2(3) . . . . ?
N1 C8 C10 C11 -84.9(2) . . . . ?
N2 C9 C12 O1 64.0(3) . . . . ?
N2 C9 C12 C13 -111.5(2) . . . . ?
N2 C9 C15 C14 106.6(2) . . . . ?
N2 C9 C15 C16 -74.6(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C23 -179.9(2) . . . . ?
C1 C7 C8 N1 -25.8(2) . . . . ?
C1 C7 C8 C9 -146.85(19) . . . . ?
C1 C7 C8 C10 95.0(2) . . . . ?
C2 C1 C6 N1 -177.1(2) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C1 C7 C8 -166.5(2) . . . . ?
C2 C1 C7 C21 75.7(3) . . . . ?
C2 C1 C7 C22 -44.7(3) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 N1 177.2(2) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C6 N1 C8 C7 27.8(2) . . . . ?
C6 N1 C8 C9 153.83(18) . . . . ?
C6 N1 C8 C10 -96.2(2) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C1 C7 C8 16.1(2) . . . . ?
C6 C1 C7 C21 -101.8(2) . . . . ?
C6 C1 C7 C22 137.9(2) . . . . ?
C7 C1 C2 C3 -177.8(2) . . . . ?
C7 C1 C6 N1 0.6(3) . . . . ?
C7 C1 C6 C5 179.7(2) . . . . ?
C7 C8 C9 N2 -157.62(19) . . . . ?
C7 C8 C9 C12 -46.1(3) . . . . ?
C7 C8 C9 C15 77.4(3) . . . . ?
C7 C8 C10 C11 158.35(19) . . . . ?
C8 N1 C6 C1 -18.6(2) . . . . ?
C8 N1 C6 C5 162.3(2) . . . . ?
C8 C9 C12 O1 -45.6(3) . . . . ?
C8 C9 C12 C13 139.0(2) . . . . ?
C8 C9 C15 C14 -134.2(2) . . . . ?
C8 C9 C15 C16 44.5(4) . . . . ?
C8 C10 C11 S1 161.23(17) . . . . ?
C8 C10 C11 N2 -18.6(2) . . . . ?
C9 N2 C11 S1 176.64(17) . . . . ?
C9 N2 C11 C10 -3.5(3) . . . . ?
C9 C8 C10 C11 31.1(2) . . . . ?
C9 C12 C13 C14 -5.7(3) . . . . ?
C9 C12 C13 C20 177.7(2) . . . . ?
C9 C15 C16 C17 -179.5(2) . . . . ?
C10 C8 C9 N2 -31.7(2) . . . . ?
C10 C8 C9 C12 79.8(2) . . . . ?
C10 C8 C9 C15 -156.7(2) . . . . ?
C11 N2 C9 C8 23.5(3) . . . . ?
C11 N2 C9 C12 -96.4(2) . . . . ?
C11 N2 C9 C15 153.5(2) . . . . ?
C12 C9 C15 C14 -4.7(2) . . . . ?
C12 C9 C15 C16 174.1(3) . . . . ?
C12 C13 C14 C15 2.8(3) . . . . ?
C12 C13 C14 C19 -176.6(3) . . . . ?
C13 C14 C15 C9 1.6(3) . . . . ?
C13 C14 C15 C16 -177.3(2) . . . . ?
C13 C14 C19 C18 177.0(3) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C9 C12 O1 -178.3(2) . . . . ?
C15 C9 C12 C13 6.3(2) . . . . ?
C15 C14 C19 C18 -2.2(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C14 1.3(4) . . . . ?
C19 C14 C15 C9 -179.0(2) . . . . ?
C19 C14 C15 C16 2.1(4) . . . . ?
C20 C13 C14 C15 179.3(2) . . . . ?
C20 C13 C14 C19 -0.1(4) . . . . ?
C21 C7 C8 N1 88.5(2) . . . . ?
C21 C7 C8 C9 -32.6(3) . . . . ?
C21 C7 C8 C10 -150.8(2) . . . . ?
C22 C7 C8 N1 -144.89(19) . . . . ?
C22 C7 C8 C9 94.0(2) . . . . ?
C22 C7 C8 C10 -24.1(3) . . . . ?
C23 C3 C4 C5 -179.8(2) . . . . ?
C24 N1 C6 C1 -158.7(2) . . . . ?
C24 N1 C6 C5 22.2(3) . . . . ?
C24 N1 C8 C7 165.81(19) . . . . ?
C24 N1 C8 C9 -68.1(3) . . . . ?
C24 N1 C8 C10 41.9(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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.538
