# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_201905118
_database_code_depnum_ccdc_archive 'CCDC 1972117'
loop_
_audit_author_name
_audit_author_address
'Jian-Qiang Zhao'
;Chengdu University
China
;
_audit_update_record             
;
2019-12-16 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;
_audit_creation_date             2019-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N3 O3 S'
_chemical_formula_sum            'C25 H23 N3 O3 S'
_chemical_formula_weight         445.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Co1
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      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                   8.3770(5)
_cell_length_b                   23.6227(13)
_cell_length_c                   12.1418(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.819(7)
_cell_angle_gamma                90
_cell_volume                     2260.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2570
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8870
_cell_measurement_theta_min      4.2930
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    1.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8914
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.742
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   11.00   37.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -66.00  -34.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega -100.00  -72.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   -7.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   78.00  106.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00    8.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega   13.00   39.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   72.00  105.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  9 omega   18.00   68.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega   79.00  110.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega   20.00   53.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 12 omega   13.00   39.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   57.00   82.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   80.00  125.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 15 omega  108.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 68

#__ type_ start__ end____ width___ exp.time_
 16 omega   62.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   48.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
 18 omega  102.00  166.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
 19 omega   88.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
 20 omega  119.00  153.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 22 omega   56.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 23 omega   38.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0284780000
_diffrn_orient_matrix_UB_12      -0.0314785000
_diffrn_orient_matrix_UB_13      0.1029424000
_diffrn_orient_matrix_UB_21      0.0297243000
_diffrn_orient_matrix_UB_22      0.0556036000
_diffrn_orient_matrix_UB_23      0.0705264000
_diffrn_orient_matrix_UB_31      -0.1911226000
_diffrn_orient_matrix_UB_32      0.0133704000
_diffrn_orient_matrix_UB_33      -0.0512411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3133
_reflns_number_total             4023
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.050
_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)+(0.0549P)²+0.3063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1235
_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:
 C9(H9A,H9B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_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
C1 C 1.0230(3) 0.33542(11) 0.0928(2) 0.0517(6) Uani 1 1 d . . . . .
H1 H 0.9932 0.3708 0.1133 0.062 Uiso 1 1 calc R . . . .
C2 C 1.1762(3) 0.32760(15) 0.0741(3) 0.0693(8) Uani 1 1 d . . . . .
H2 H 1.2493 0.3581 0.0812 0.083 Uiso 1 1 calc R . . . .
C3 C 1.2200(3) 0.27512(16) 0.0453(3) 0.0772(9) Uani 1 1 d . . . . .
H3 H 1.3229 0.2708 0.0328 0.093 Uiso 1 1 calc R . . . .
C4 C 1.1153(3) 0.22828(14) 0.0341(2) 0.0670(8) Uani 1 1 d . . . . .
H4 H 1.1464 0.1928 0.0149 0.080 Uiso 1 1 calc R . . . .
C5 C 0.9625(3) 0.23658(11) 0.05289(19) 0.0472(5) Uani 1 1 d . . . . .
C6 C 0.9161(2) 0.28979(10) 0.08031(18) 0.0414(5) Uani 1 1 d . . . . .
C7 C 0.7466(2) 0.28426(9) 0.09717(18) 0.0386(4) Uani 1 1 d . . . . .
C8 C 0.7034(3) 0.22097(9) 0.0703(2) 0.0440(5) Uani 1 1 d . . . . .
C9 C 0.7452(3) 0.30147(9) 0.21836(19) 0.0424(5) Uani 1 1 d . . . . .
H9A H 0.6732 0.2767 0.2448 0.051 Uiso 1 1 calc R . . . .
H9B H 0.8587 0.3015 0.2758 0.051 Uiso 1 1 calc R . . . .
C10 C 0.6731(2) 0.36049(9) 0.19493(18) 0.0374(4) Uani 1 1 d . . . . .
C11 C 0.6794(3) 0.40175(9) 0.28653(19) 0.0412(5) Uani 1 1 d . . . . .
C12 C 0.7890(4) 0.39326(11) 0.3999(2) 0.0569(6) Uani 1 1 d . . . . .
H12 H 0.8575 0.3612 0.4181 0.068 Uiso 1 1 calc R . . . .
C13 C 0.7964(5) 0.43236(13) 0.4855(2) 0.0783(9) Uani 1 1 d . . . . .
H13 H 0.8698 0.4264 0.5616 0.094 Uiso 1 1 calc R . . . .
C14 C 0.6969(5) 0.48002(13) 0.4602(3) 0.0813(10) Uani 1 1 d . . . . .
H14 H 0.7036 0.5063 0.5187 0.098 Uiso 1 1 calc R . . . .
C15 C 0.5874(4) 0.48884(12) 0.3484(3) 0.0689(7) Uani 1 1 d . . . . .
H15 H 0.5194 0.5210 0.3313 0.083 Uiso 1 1 calc R . . . .
C16 C 0.5777(3) 0.45027(10) 0.2615(2) 0.0536(6) Uani 1 1 d . . . . .
H16 H 0.5033 0.4565 0.1859 0.064 Uiso 1 1 calc R . . . .
C17 C 0.8390(4) 0.13756(11) 0.0164(2) 0.0647(7) Uani 1 1 d . . . . .
H17A H 0.7673 0.1157 0.0488 0.078 Uiso 1 1 calc R . . . .
H17B H 0.9537 0.1229 0.0491 0.078 Uiso 1 1 calc R . . . .
C18 C 0.7770(5) 0.13050(14) -0.1151(3) 0.0849(10) Uani 1 1 d . . . . .
H18A H 0.8419 0.1545 -0.1479 0.127 Uiso 1 1 calc GR . . . .
H18B H 0.6594 0.1408 -0.1467 0.127 Uiso 1 1 calc GR . . . .
H18C H 0.7905 0.0918 -0.1341 0.127 Uiso 1 1 calc GR . . . .
C19 C 0.7191(3) 0.37272(10) -0.14506(18) 0.0438(5) Uani 1 1 d . . . . .
C20 C 0.7244(3) 0.42975(11) -0.1169(2) 0.0559(6) Uani 1 1 d . . . . .
H20 H 0.6444 0.4453 -0.0881 0.067 Uiso 1 1 calc R . . . .
C21 C 0.8509(4) 0.46305(12) -0.1324(2) 0.0662(7) Uani 1 1 d . . . . .
H21 H 0.8554 0.5014 -0.1140 0.079 Uiso 1 1 calc R . . . .
C22 C 0.9712(4) 0.44023(13) -0.1750(2) 0.0647(7) Uani 1 1 d . . . . .
C23 C 0.9612(3) 0.38356(13) -0.2040(2) 0.0607(7) Uani 1 1 d . . . . .
H23 H 1.0400 0.3681 -0.2340 0.073 Uiso 1 1 calc R . . . .
C24 C 0.8359(3) 0.34937(11) -0.1891(2) 0.0527(6) Uani 1 1 d . . . . .
H24 H 0.8304 0.3112 -0.2086 0.063 Uiso 1 1 calc R . . . .
C25 C 1.1106(5) 0.47705(18) -0.1902(4) 0.1023(13) Uani 1 1 d . . . . .
H25A H 1.0627 0.5119 -0.2275 0.153 Uiso 1 1 calc GR . . . .
H25B H 1.1640 0.4576 -0.2378 0.153 Uiso 1 1 calc GR . . . .
H25C H 1.1934 0.4850 -0.1149 0.153 Uiso 1 1 calc GR . . . .
N1 N 0.8371(3) 0.19650(8) 0.04970(17) 0.0492(5) Uani 1 1 d . . . . .
N2 N 0.6089(2) 0.32192(7) 0.02315(15) 0.0394(4) Uani 1 1 d . . . . .
N3 N 0.5974(2) 0.37105(7) 0.08603(15) 0.0392(4) Uani 1 1 d . . . . .
O1 O 0.5747(2) 0.19738(7) 0.07119(18) 0.0617(5) Uani 1 1 d . . . . .
O2 O 0.5821(2) 0.27337(7) -0.15880(15) 0.0583(4) Uani 1 1 d . . . . .
O3 O 0.4056(2) 0.35822(9) -0.16187(16) 0.0671(5) Uani 1 1 d . . . . .
S1 S 0.56362(6) 0.32932(3) -0.12012(5) 0.04539(17) 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 H1 0.9300 . ?
C1 C2 1.389(3) . ?
C1 C6 1.376(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(3) . ?
C5 C6 1.389(3) . ?
C5 N1 1.405(3) . ?
C6 C7 1.508(3) . ?
C7 C8 1.547(3) . ?
C7 C9 1.531(3) . ?
C7 N2 1.492(3) . ?
C8 N1 1.357(3) . ?
C8 O1 1.217(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.508(3) . ?
C10 C11 1.466(3) . ?
C10 N3 1.282(3) . ?
C11 C12 1.386(3) . ?
C11 C16 1.399(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.512(4) . ?
C17 N1 1.451(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.387(3) . ?
C19 C24 1.379(3) . ?
C19 S1 1.763(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(4) . ?
C22 C23 1.379(4) . ?
C22 C25 1.517(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(3) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N2 N3 1.410(2) . ?
N2 S1 1.6592(17) . ?
O2 S1 1.4284(18) . ?
O3 S1 1.4213(18) . ?

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 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C6 C1 C2 118.7(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 N1 128.5(2) . . ?
C6 C5 N1 110.44(18) . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 C7 131.3(2) . . ?
C5 C6 C7 107.88(19) . . ?
C6 C7 C8 102.63(17) . . ?
C6 C7 C9 114.97(17) . . ?
C9 C7 C8 112.48(17) . . ?
N2 C7 C6 115.96(17) . . ?
N2 C7 C8 111.82(17) . . ?
N2 C7 C9 99.46(15) . . ?
N1 C8 C7 107.60(18) . . ?
O1 C8 C7 125.8(2) . . ?
O1 C8 N1 126.6(2) . . ?
C7 C9 H9A 111.5 . . ?
C7 C9 H9B 111.5 . . ?
H9A C9 H9B 109.3 . . ?
C10 C9 C7 101.39(17) . . ?
C10 C9 H9A 111.5 . . ?
C10 C9 H9B 111.5 . . ?
C11 C10 C9 124.22(18) . . ?
N3 C10 C9 113.63(18) . . ?
N3 C10 C11 122.07(19) . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 C16 118.9(2) . . ?
C16 C11 C10 121.2(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
N1 C17 H17A 109.3 . . ?
N1 C17 H17B 109.3 . . ?
N1 C17 C18 111.6(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 S1 119.11(18) . . ?
C24 C19 C20 121.1(2) . . ?
C24 C19 S1 119.77(18) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.7(2) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.1(3) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C25 120.6(3) . . ?
C23 C22 C21 118.9(2) . . ?
C23 C22 C25 120.6(3) . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 121.1(2) . . ?
C24 C23 H23 119.5 . . ?
C19 C24 C23 119.1(2) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C5 N1 C17 125.1(2) . . ?
C8 N1 C5 111.33(19) . . ?
C8 N1 C17 123.2(2) . . ?
C7 N2 S1 123.34(13) . . ?
N3 N2 C7 110.20(16) . . ?
N3 N2 S1 116.58(14) . . ?
C10 N3 N2 107.31(17) . . ?
N2 S1 C19 108.76(9) . . ?
O2 S1 C19 108.25(11) . . ?
O2 S1 N2 103.62(10) . . ?
O3 S1 C19 108.20(11) . . ?
O3 S1 N2 106.19(10) . . ?
O3 S1 O2 121.24(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
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C6 C7 C8 -178.9(2) . . . . ?
C1 C6 C7 C9 -56.5(3) . . . . ?
C1 C6 C7 N2 58.9(3) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C1 C6 C7 178.2(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C5 N1 -178.4(2) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C4 C5 C6 C7 -179.0(2) . . . . ?
C4 C5 N1 C8 -178.7(2) . . . . ?
C4 C5 N1 C17 -5.0(4) . . . . ?
C5 C6 C7 C8 -2.2(2) . . . . ?
C5 C6 C7 C9 120.3(2) . . . . ?
C5 C6 C7 N2 -124.3(2) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C6 C5 N1 C8 2.0(3) . . . . ?
C6 C5 N1 C17 175.8(2) . . . . ?
C6 C7 C8 N1 3.3(2) . . . . ?
C6 C7 C8 O1 -178.7(2) . . . . ?
C6 C7 C9 C10 99.5(2) . . . . ?
C6 C7 N2 N3 -96.2(2) . . . . ?
C6 C7 N2 S1 48.2(2) . . . . ?
C7 C8 N1 C5 -3.4(2) . . . . ?
C7 C8 N1 C17 -177.3(2) . . . . ?
C7 C9 C10 C11 -165.54(18) . . . . ?
C7 C9 C10 N3 17.5(2) . . . . ?
C7 N2 N3 C10 -18.3(2) . . . . ?
C7 N2 S1 C19 -75.97(18) . . . . ?
C7 N2 S1 O2 39.03(18) . . . . ?
C7 N2 S1 O3 167.78(16) . . . . ?
C8 C7 C9 C10 -143.55(17) . . . . ?
C8 C7 N2 N3 146.61(16) . . . . ?
C8 C7 N2 S1 -69.0(2) . . . . ?
C9 C7 C8 N1 -120.77(19) . . . . ?
C9 C7 C8 O1 57.2(3) . . . . ?
C9 C7 N2 N3 27.64(19) . . . . ?
C9 C7 N2 S1 172.02(14) . . . . ?
C9 C10 C11 C12 15.8(3) . . . . ?
C9 C10 C11 C16 -165.0(2) . . . . ?
C9 C10 N3 N2 -0.3(2) . . . . ?
C10 C11 C12 C13 179.2(2) . . . . ?
C10 C11 C16 C15 -179.1(2) . . . . ?
C11 C10 N3 N2 -177.35(16) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C18 C17 N1 C5 -80.8(3) . . . . ?
C18 C17 N1 C8 92.3(3) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C19 C24 C23 0.7(4) . . . . ?
C20 C19 S1 N2 -69.5(2) . . . . ?
C20 C19 S1 O2 178.54(18) . . . . ?
C20 C19 S1 O3 45.4(2) . . . . ?
C20 C21 C22 C23 1.2(4) . . . . ?
C20 C21 C22 C25 -179.2(3) . . . . ?
C21 C22 C23 C24 -1.2(4) . . . . ?
C22 C23 C24 C19 0.3(4) . . . . ?
C24 C19 C20 C21 -0.8(4) . . . . ?
C24 C19 S1 N2 108.78(19) . . . . ?
C24 C19 S1 O2 -3.2(2) . . . . ?
C24 C19 S1 O3 -136.28(19) . . . . ?
C25 C22 C23 C24 179.2(3) . . . . ?
N1 C5 C6 C1 177.48(19) . . . . ?
N1 C5 C6 C7 0.3(2) . . . . ?
N2 C7 C8 N1 128.30(18) . . . . ?
N2 C7 C8 O1 -53.8(3) . . . . ?
N2 C7 C9 C10 -25.08(18) . . . . ?
N3 C10 C11 C12 -167.4(2) . . . . ?
N3 C10 C11 C16 11.8(3) . . . . ?
N3 N2 S1 C19 66.35(16) . . . . ?
N3 N2 S1 O2 -178.65(14) . . . . ?
N3 N2 S1 O3 -49.90(16) . . . . ?
O1 C8 N1 C5 178.7(2) . . . . ?
O1 C8 N1 C17 4.8(4) . . . . ?
S1 C19 C20 C21 177.5(2) . . . . ?
S1 C19 C24 C23 -177.52(18) . . . . ?
S1 N2 N3 C10 -165.32(13) . . . . ?

_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_201912317
_database_code_depnum_ccdc_archive 'CCDC 1972118'
loop_
_audit_author_name
_audit_author_address
'Jian-Qiang Zhao'
;Chengdu University
China
;
_audit_update_record             
;
2019-12-16 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;
_audit_creation_date             2019-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 N2 O3 S'
_chemical_formula_sum            'C24 H20 N2 O3 S'
_chemical_formula_weight         416.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4S1
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      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                   11.3284(5)
_cell_length_b                   8.7436(6)
_cell_length_c                   20.6742(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.103(4)
_cell_angle_gamma                90
_cell_volume                     2036.18(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2250
_cell_measurement_theta_min      4.2640
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.053
_diffrn_reflns_theta_max         67.053
_diffrn_reflns_theta_min         4.270
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -32.00   1.00    1.00    --  -33.50 178.00 150.00   76
  2  ω   -102.00 -44.00   1.00    1.00    --  -33.50 -57.00 120.00   58
  3  ω    -72.00 -19.00   1.00    1.00    --  -33.50 -37.00-150.00   53
  4  ω     71.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   39
  5  ω     36.00 103.00   1.00    1.00    --   36.47  57.00  60.00   67
  6  ω     -3.00  75.00   1.00    1.00    --   36.47 -99.00 -30.00   78
  7  ω     59.00  94.00   1.00    1.00    --   36.47  57.00   0.00   35
  8  ω    139.00 172.00   1.00    2.50    --  108.00  45.00-180.00   33
  9  ω     38.00 123.00   1.00    2.50    --  108.00 -30.00-120.00   85
 10  ω     88.00 119.00   1.00    2.50    --  108.00  45.00-180.00   31
 11  ω     49.00 105.00   1.00    2.50    --  108.00 -94.00 -90.00   56
 12  ω     99.00 128.00   1.00    2.50    --  108.00 -15.00   0.00   29
 13  ω    113.00 141.00   1.00    2.50    --  108.00  61.00-150.00   28
 14  ω     51.00 109.00   1.00    2.50    --  108.00 -94.00-180.00   58
 15  ω     36.00  96.00   1.00    2.50    --  108.00 -15.00   0.00   60
 16  ω    113.00 139.00   1.00    2.50    --  108.00 111.00 -90.00   26
 17  ω     51.00 128.00   1.00    2.50    --  108.00 -61.00 -30.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0134691000
_diffrn_orient_matrix_UB_12      0.0435411000
_diffrn_orient_matrix_UB_13      0.0726445000
_diffrn_orient_matrix_UB_21      -0.1357542000
_diffrn_orient_matrix_UB_22      -0.0069431000
_diffrn_orient_matrix_UB_23      0.0003141000
_diffrn_orient_matrix_UB_31      0.0088524000
_diffrn_orient_matrix_UB_32      -0.1708763000
_diffrn_orient_matrix_UB_33      0.0185101000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2656
_reflns_number_total             3620
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00134(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.030
_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)+(0.0633P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1362
_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:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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 0.57133(6) 1.01979(8) 0.26019(3) 0.0497(2) Uani 1 1 d . . . . .
O1 O 0.41205(17) 1.0648(2) 0.41522(11) 0.0659(6) Uani 1 1 d . . . . .
O2 O 0.67397(17) 1.0370(3) 0.22622(9) 0.0648(6) Uani 1 1 d . . . . .
O3 O 0.48366(17) 1.1386(2) 0.25682(10) 0.0645(5) Uani 1 1 d . . . . .
N1 N 0.61108(19) 0.9995(2) 0.33977(10) 0.0501(5) Uani 1 1 d . . . . .
N2 N 0.70999(19) 0.9036(2) 0.35440(10) 0.0494(5) Uani 1 1 d . . . . .
C1 C 0.3754(3) 1.4147(4) 0.42377(16) 0.0687(8) Uani 1 1 d . . . . .
H1 H 0.3082 1.3675 0.4367 0.082 Uiso 1 1 calc R . . . .
C2 C 0.3845(3) 1.5711(4) 0.42209(19) 0.0823(10) Uani 1 1 d . . . . .
H2 H 0.3223 1.6308 0.4339 0.099 Uiso 1 1 calc R . . . .
C3 C 0.4844(4) 1.6415(4) 0.40311(18) 0.0799(10) Uani 1 1 d . . . . .
H3 H 0.4882 1.7477 0.4023 0.096 Uiso 1 1 calc R . . . .
C4 C 0.5789(3) 1.5565(3) 0.38535(15) 0.0660(8) Uani 1 1 d . . . . .
H4 H 0.6463 1.6046 0.3731 0.079 Uiso 1 1 calc R . . . .
C5 C 0.5709(2) 1.3986(3) 0.38612(12) 0.0504(6) Uani 1 1 d . . . . .
C6 C 0.4702(2) 1.3286(3) 0.40540(13) 0.0519(6) Uani 1 1 d . . . . .
C7 C 0.4828(2) 1.1617(3) 0.40363(12) 0.0496(6) Uani 1 1 d . . . . .
C8 C 0.6583(2) 1.2836(3) 0.36579(13) 0.0529(6) Uani 1 1 d . . . . .
H8A H 0.7370 1.3023 0.3877 0.064 Uiso 1 1 calc R . . . .
H8B H 0.6619 1.2870 0.3191 0.064 Uiso 1 1 calc R . . . .
C9 C 0.6096(2) 1.1279(3) 0.38651(12) 0.0467(6) Uani 1 1 d . . . . .
C10 C 0.6841(2) 1.0537(3) 0.44530(12) 0.0500(6) Uani 1 1 d . . . . .
H10A H 0.7375 1.1273 0.4681 0.060 Uiso 1 1 calc R . . . .
H10B H 0.6337 1.0098 0.4756 0.060 Uiso 1 1 calc R . . . .
C11 C 0.7515(2) 0.9321(3) 0.41363(11) 0.0441(6) Uani 1 1 d . . . . .
C12 C 0.8529(2) 0.8448(3) 0.44442(12) 0.0452(6) Uani 1 1 d . . . . .
C13 C 0.8872(3) 0.8561(3) 0.51099(13) 0.0574(7) Uani 1 1 d . . . . .
H13 H 0.8453 0.9194 0.5366 0.069 Uiso 1 1 calc R . . . .
C14 C 0.9833(3) 0.7738(4) 0.53914(14) 0.0668(8) Uani 1 1 d . . . . .
H14 H 1.0053 0.7820 0.5836 0.080 Uiso 1 1 calc R . . . .
C15 C 1.0464(3) 0.6806(4) 0.50253(15) 0.0643(8) Uani 1 1 d . . . . .
H15 H 1.1114 0.6263 0.5218 0.077 Uiso 1 1 calc R . . . .
C16 C 1.0125(3) 0.6679(4) 0.43645(15) 0.0651(8) Uani 1 1 d . . . . .
H16 H 1.0548 0.6044 0.4111 0.078 Uiso 1 1 calc R . . . .
C17 C 0.9167(2) 0.7486(3) 0.40809(13) 0.0566(7) Uani 1 1 d . . . . .
H17 H 0.8943 0.7383 0.3637 0.068 Uiso 1 1 calc R . . . .
C18 C 0.5038(2) 0.8452(3) 0.23675(11) 0.0448(6) Uani 1 1 d . . . . .
C19 C 0.5720(2) 0.7149(3) 0.23261(12) 0.0507(6) Uani 1 1 d . . . . .
H19 H 0.6538 0.7190 0.2431 0.061 Uiso 1 1 calc R . . . .
C20 C 0.5180(2) 0.5790(3) 0.21291(13) 0.0528(6) Uani 1 1 d . . . . .
H20 H 0.5639 0.4913 0.2110 0.063 Uiso 1 1 calc R . . . .
C21 C 0.3957(2) 0.5705(3) 0.19582(12) 0.0497(6) Uani 1 1 d . . . . .
C22 C 0.3297(2) 0.7040(3) 0.20010(14) 0.0583(7) Uani 1 1 d . . . . .
H22 H 0.2480 0.7009 0.1890 0.070 Uiso 1 1 calc R . . . .
C23 C 0.3824(2) 0.8406(3) 0.22043(14) 0.0548(7) Uani 1 1 d . . . . .
H23 H 0.3368 0.9283 0.2231 0.066 Uiso 1 1 calc R . . . .
C24 C 0.3379(3) 0.4237(4) 0.17248(17) 0.0684(8) Uani 1 1 d . . . . .
H24A H 0.3517 0.3473 0.2058 0.103 Uiso 1 1 calc GR . . . .
H24B H 0.3709 0.3902 0.1340 0.103 Uiso 1 1 calc GR . . . .
H24C H 0.2540 0.4395 0.1627 0.103 Uiso 1 1 calc GR . . . .


_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 O2 1.429(2) . ?
S1 O3 1.434(2) . ?
S1 N1 1.668(2) . ?
S1 C18 1.753(3) . ?
O1 C7 1.207(3) . ?
N1 N2 1.406(3) . ?
N1 C9 1.483(3) . ?
N2 C11 1.288(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(5) . ?
C1 C6 1.396(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C5 C6 1.389(4) . ?
C5 C8 1.502(4) . ?
C6 C7 1.468(4) . ?
C7 C9 1.544(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.546(3) . ?
C9 C10 1.547(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.499(4) . ?
C11 C12 1.467(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.382(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(4) . ?
C18 C23 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.395(3) . ?
C21 C22 1.394(4) . ?
C21 C24 1.497(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O2 S1 O3 119.71(13) . . ?
O2 S1 N1 110.34(11) . . ?
O2 S1 C18 108.05(13) . . ?
O3 S1 N1 103.77(12) . . ?
O3 S1 C18 109.75(12) . . ?
N1 S1 C18 104.12(11) . . ?
N2 N1 S1 113.63(17) . . ?
N2 N1 C9 112.04(19) . . ?
C9 N1 S1 122.78(16) . . ?
C11 N2 N1 106.9(2) . . ?
C2 C1 H1 121.0 . . ?
C2 C1 C6 117.9(3) . . ?
C6 C1 H1 121.0 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 C8 128.2(3) . . ?
C6 C5 C8 111.8(2) . . ?
C1 C6 C7 128.5(3) . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 C7 110.2(2) . . ?
O1 C7 C6 128.7(3) . . ?
O1 C7 C9 124.4(3) . . ?
C6 C7 C9 106.9(2) . . ?
C5 C8 H8A 110.9 . . ?
C5 C8 H8B 110.9 . . ?
C5 C8 C9 104.3(2) . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
N1 C9 C7 111.7(2) . . ?
N1 C9 C8 117.2(2) . . ?
N1 C9 C10 98.70(19) . . ?
C7 C9 C8 105.3(2) . . ?
C7 C9 C10 110.1(2) . . ?
C8 C9 C10 114.0(2) . . ?
C9 C10 H10A 111.3 . . ?
C9 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
C11 C10 C9 102.4(2) . . ?
C11 C10 H10A 111.3 . . ?
C11 C10 H10B 111.3 . . ?
N2 C11 C10 113.6(2) . . ?
N2 C11 C12 120.1(2) . . ?
C12 C11 C10 126.2(2) . . ?
C13 C12 C11 121.0(2) . . ?
C17 C12 C11 120.7(2) . . ?
C17 C12 C13 118.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17 119.5 . . ?
C19 C18 S1 120.27(19) . . ?
C23 C18 S1 119.1(2) . . ?
C23 C18 C19 120.6(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C24 121.0(3) . . ?
C22 C21 C20 117.7(3) . . ?
C22 C21 C24 121.3(2) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.7(2) . . ?
C23 C22 H22 119.1 . . ?
C18 C23 C22 119.2(3) . . ?
C18 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 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
S1 N1 N2 C11 161.84(17) . . . . ?
S1 N1 C9 C7 78.6(3) . . . . ?
S1 N1 C9 C8 -42.9(3) . . . . ?
S1 N1 C9 C10 -165.63(18) . . . . ?
S1 C18 C19 C20 -178.7(2) . . . . ?
S1 C18 C23 C22 178.1(2) . . . . ?
O1 C7 C9 N1 43.4(3) . . . . ?
O1 C7 C9 C8 171.6(3) . . . . ?
O1 C7 C9 C10 -65.1(3) . . . . ?
O2 S1 N1 N2 -41.6(2) . . . . ?
O2 S1 N1 C9 98.6(2) . . . . ?
O2 S1 C18 C19 44.2(2) . . . . ?
O2 S1 C18 C23 -133.6(2) . . . . ?
O3 S1 N1 N2 -171.02(17) . . . . ?
O3 S1 N1 C9 -30.8(2) . . . . ?
O3 S1 C18 C19 176.3(2) . . . . ?
O3 S1 C18 C23 -1.5(2) . . . . ?
N1 S1 C18 C19 -73.1(2) . . . . ?
N1 S1 C18 C23 109.0(2) . . . . ?
N1 N2 C11 C10 -0.6(3) . . . . ?
N1 N2 C11 C12 177.4(2) . . . . ?
N1 C9 C10 C11 21.9(2) . . . . ?
N2 N1 C9 C7 -140.6(2) . . . . ?
N2 N1 C9 C8 97.9(2) . . . . ?
N2 N1 C9 C10 -24.8(3) . . . . ?
N2 C11 C12 C13 -169.6(3) . . . . ?
N2 C11 C12 C17 10.1(4) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C1 C6 C7 O1 3.2(5) . . . . ?
C1 C6 C7 C9 -174.3(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C1 C6 C7 179.3(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 C8 176.6(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C4 C5 C6 C7 -178.8(2) . . . . ?
C4 C5 C8 C9 172.4(3) . . . . ?
C5 C6 C7 O1 -177.6(3) . . . . ?
C5 C6 C7 C9 4.9(3) . . . . ?
C5 C8 C9 N1 137.0(2) . . . . ?
C5 C8 C9 C7 12.2(3) . . . . ?
C5 C8 C9 C10 -108.5(2) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C6 C5 C8 C9 -9.9(3) . . . . ?
C6 C7 C9 N1 -138.9(2) . . . . ?
C6 C7 C9 C8 -10.7(3) . . . . ?
C6 C7 C9 C10 112.5(2) . . . . ?
C7 C9 C10 C11 138.9(2) . . . . ?
C8 C5 C6 C1 -177.4(3) . . . . ?
C8 C5 C6 C7 3.3(3) . . . . ?
C8 C9 C10 C11 -103.1(2) . . . . ?
C9 N1 N2 C11 17.3(3) . . . . ?
C9 C10 C11 N2 -14.7(3) . . . . ?
C9 C10 C11 C12 167.4(2) . . . . ?
C10 C11 C12 C13 8.1(4) . . . . ?
C10 C11 C12 C17 -172.2(3) . . . . ?
C11 C12 C13 C14 -179.7(3) . . . . ?
C11 C12 C17 C16 179.3(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C12 C17 C16 -1.0(4) . . . . ?
C13 C14 C15 C16 -0.6(5) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C16 C17 C12 0.6(5) . . . . ?
C17 C12 C13 C14 0.6(4) . . . . ?
C18 S1 N1 N2 74.12(19) . . . . ?
C18 S1 N1 C9 -145.6(2) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C19 C18 C23 C22 0.2(4) . . . . ?
C19 C20 C21 C22 -0.8(4) . . . . ?
C19 C20 C21 C24 178.1(3) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C22 C23 C18 0.2(4) . . . . ?
C23 C18 C19 C20 -0.9(4) . . . . ?
C24 C21 C22 C23 -178.8(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 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.896
