# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_lsh-43
_database_code_depnum_ccdc_archive 'CCDC 2287281'
loop_
_audit_author_name
_audit_author_address
'Nengzhong Wang'
;China Three Gorges University
China
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-05-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O4 S'
_chemical_formula_sum            'C19 H19 N O4 S'
_chemical_formula_weight         357.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C76 H68 N4 O16 S4 '
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.30100(10)
_cell_length_b                   11.06510(10)
_cell_length_c                   18.7113(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.4680(10)
_cell_angle_gamma                90
_cell_volume                     1715.51(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15158
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9050
_cell_measurement_theta_min      4.0340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18184
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.395
_diffrn_reflns_theta_min         4.645
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00   8.00   0.50    0.50    --    0.00 -82.00 -60.00   64
  2  ω    -70.00 -21.00   0.50    0.50    --    0.00 -38.00 -90.00   98
  3  ω    -88.00 -20.00   0.50    0.50    --    0.00 -57.00 -30.00  136
  4  ω    -27.00  31.00   0.50    0.50    --    0.00 -82.00-150.00  116
  5  ω    -33.00  29.00   0.50    0.50    --    0.00 -82.00  30.00  124
  6  ω     -7.00  22.00   0.50    0.50    --    0.00 -57.00 -30.00   58
  7  ω     21.00 104.00   0.50    0.56    --   95.80 -15.00 -60.00  166
  8  ω    156.00 181.00   0.50    0.56    --   95.80  64.00 -38.58   50
  9  ω     71.00  97.00   0.50    0.56    --   95.80  63.00 -69.18   52
 10  ω    120.00 170.00   0.50    0.56    --   95.80  53.00-118.51  100
 11  ω    128.00 184.00   0.50    0.56    --   95.80  62.00 -82.81  112
 12  ω      6.00 110.00   0.50    0.56    --   95.80 -30.00 -60.00  208
 13  ω     74.00 100.00   0.50    0.56    --   95.80  61.00 -60.00   52
 14  ω     72.00 160.00   0.50    0.56    --   95.80  66.00 -19.94  176
 15  ω     74.00 107.00   0.50    0.56    --   95.80  53.00-118.51   66
 16  ω     71.00 150.00   0.50    0.56    --   95.80  64.00 -38.58  158
 17  ω     77.00 102.00   0.50    0.56    --   95.80  45.00 -30.00   50
 18  ω     81.00 184.00   0.50    0.56    --   95.80  77.00  90.00  206
 19  ω     61.00 118.00   0.50    0.56    --   95.80 -77.00 -60.00  114
 20  ω     72.00  98.00   0.50    0.56    --   95.80  15.00 150.00   52
 21  ω    135.00 161.00   0.50    0.56    --   95.80  15.00 150.00   52
 22  ω     72.00  98.00   0.50    0.56    --   95.80  62.00 -82.81   52
 23  ω     89.00 143.00   0.50    0.56    --   95.80  61.00 120.00  108
 24  ω    122.00 185.00   0.50    0.56    --   95.80  63.00 -69.18  126
 25  ω     92.00 118.00   0.50    0.56    --   95.80  82.00  60.00   52
 26  ω    129.00 179.00   0.50    0.56    --   95.80  82.00  60.00  100
 27  ω     81.00 110.00   0.50    0.56    --   95.80  40.00 -70.72   58
 28  ω     76.00 105.00   0.50    0.56    --   95.80  45.00 -90.00   58
 29  ω    115.00 160.00   0.50    0.56    --   95.80  45.00 -90.00   90
 30  ω     76.00 102.00   0.50    0.56    --   95.80  52.00 -61.38   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1452875000
_diffrn_orient_matrix_UB_12      0.0487743000
_diffrn_orient_matrix_UB_13      -0.0463289000
_diffrn_orient_matrix_UB_21      -0.1155667000
_diffrn_orient_matrix_UB_22      -0.0643879000
_diffrn_orient_matrix_UB_23      0.0488166000
_diffrn_orient_matrix_UB_31      -0.0031468000
_diffrn_orient_matrix_UB_32      0.1135324000
_diffrn_orient_matrix_UB_33      0.0477825000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3401
_reflns_number_total             3454
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0071(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.6821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0772
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.52998(3) 0.27744(2) 0.43353(2) 0.02205(10) Uani 1 1 d . . . . .
O1 O 0.47413(10) 0.16682(8) 0.40131(5) 0.0295(2) Uani 1 1 d . . . . .
O2 O 0.41996(10) 0.37485(8) 0.44333(5) 0.0291(2) Uani 1 1 d . . . . .
O3 O 0.75432(11) 0.69848(8) 0.40096(5) 0.0300(2) Uani 1 1 d . . . . .
O4 O 0.62321(13) 0.74626(9) 0.29634(5) 0.0391(2) Uani 1 1 d . . . . .
N1 N 0.66795(11) 0.33246(8) 0.38369(5) 0.0233(2) Uani 1 1 d . . . . .
C1 C 0.93552(14) 0.33372(11) 0.35713(6) 0.0277(3) Uani 1 1 d . . . . .
C2 C 1.07427(16) 0.28691(13) 0.32990(7) 0.0364(3) Uani 1 1 d . . . . .
H2 H 1.168811 0.334984 0.328312 0.044 Uiso 1 1 calc R U . . .
C3 C 1.07271(17) 0.16868(14) 0.30503(7) 0.0401(3) Uani 1 1 d . . . . .
H3 H 1.166774 0.135681 0.286055 0.048 Uiso 1 1 calc R U . . .
C4 C 0.93542(17) 0.09866(13) 0.30765(7) 0.0364(3) Uani 1 1 d . . . . .
H4 H 0.937306 0.017605 0.290981 0.044 Uiso 1 1 calc R U . . .
C5 C 0.79409(16) 0.14408(11) 0.33418(6) 0.0291(3) Uani 1 1 d . . . . .
H5 H 0.699698 0.095841 0.335771 0.035 Uiso 1 1 calc R U . . .
C6 C 0.79734(14) 0.26262(11) 0.35812(6) 0.0232(2) Uani 1 1 d . . . . .
C7 C 0.90678(15) 0.45460(12) 0.39003(7) 0.0310(3) Uani 1 1 d . . . . .
H7A H 0.947487 0.520571 0.360252 0.037 Uiso 1 1 calc R U . . .
H7B H 0.959867 0.459972 0.438744 0.037 Uiso 1 1 calc R U . . .
C8 C 0.72045(14) 0.46079(10) 0.39249(6) 0.0234(2) Uani 1 1 d . . . . .
H8 H 0.690330 0.492518 0.439912 0.028 Uiso 1 1 calc R U . . .
C9 C 0.64555(13) 0.53815(11) 0.33257(6) 0.0240(2) Uani 1 1 d . . . . .
C10 C 0.56481(15) 0.49601(13) 0.27462(7) 0.0334(3) Uani 1 1 d . . . . .
H10A H 0.524062 0.550248 0.238550 0.040 Uiso 1 1 calc R U . . .
H10B H 0.547636 0.411551 0.269133 0.040 Uiso 1 1 calc R U . . .
C11 C 0.67035(14) 0.67153(11) 0.33947(6) 0.0268(3) Uani 1 1 d . . . . .
C12 C 0.78808(17) 0.82523(11) 0.41439(8) 0.0366(3) Uani 1 1 d . . . . .
H12A H 0.686215 0.871072 0.417125 0.044 Uiso 1 1 calc R U . . .
H12B H 0.849323 0.859724 0.375438 0.044 Uiso 1 1 calc R U . . .
C13 C 0.88588(18) 0.83206(14) 0.48433(8) 0.0439(4) Uani 1 1 d . . . . .
H13A H 0.986005 0.786062 0.480912 0.066 Uiso 1 1 calc R U . . .
H13B H 0.823688 0.797918 0.522376 0.066 Uiso 1 1 calc R U . . .
H13C H 0.911849 0.916661 0.495415 0.066 Uiso 1 1 calc R U . . .
C14 C 0.62678(13) 0.24206(10) 0.51757(6) 0.0225(2) Uani 1 1 d . . . . .
C15 C 0.66519(15) 0.33510(11) 0.56576(6) 0.0273(3) Uani 1 1 d . . . . .
H15 H 0.638938 0.416520 0.553898 0.033 Uiso 1 1 calc R U . . .
C16 C 0.74246(16) 0.30667(13) 0.63136(7) 0.0328(3) Uani 1 1 d . . . . .
H16 H 0.770608 0.369164 0.664618 0.039 Uiso 1 1 calc R U . . .
C17 C 0.77886(16) 0.18765(13) 0.64870(7) 0.0345(3) Uani 1 1 d . . . . .
H17 H 0.831691 0.168960 0.693801 0.041 Uiso 1 1 calc R U . . .
C18 C 0.73864(16) 0.09582(12) 0.60063(7) 0.0345(3) Uani 1 1 d . . . . .
H18 H 0.762812 0.014302 0.613084 0.041 Uiso 1 1 calc R U . . .
C19 C 0.66320(14) 0.12246(11) 0.53439(7) 0.0280(3) Uani 1 1 d . . . . .
H19 H 0.636792 0.059839 0.500976 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4293(8) . ?
S1 O2 1.4317(8) . ?
S1 N1 1.6374(10) . ?
S1 C14 1.7661(12) . ?
O3 C11 1.3422(15) . ?
O3 C12 1.4492(14) . ?
O4 C11 1.2041(15) . ?
N1 C6 1.4290(14) . ?
N1 C8 1.4916(14) . ?
C1 C2 1.3876(18) . ?
C1 C6 1.3920(17) . ?
C1 C7 1.4976(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3950(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3858(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5517(16) . ?
C8 H8 1.0000 . ?
C8 C9 1.5139(16) . ?
C9 C10 1.3246(17) . ?
C9 C11 1.4946(16) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.500(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3928(17) . ?
C14 C19 1.3893(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3863(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3852(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3861(18) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.38(5) . . ?
O1 S1 N1 107.36(5) . . ?
O1 S1 C14 107.71(5) . . ?
O2 S1 N1 105.47(5) . . ?
O2 S1 C14 108.19(5) . . ?
N1 S1 C14 107.05(5) . . ?
C11 O3 C12 116.65(10) . . ?
C6 N1 S1 123.74(8) . . ?
C6 N1 C8 109.34(9) . . ?
C8 N1 S1 120.06(8) . . ?
C2 C1 C6 119.80(12) . . ?
C2 C1 C7 129.85(12) . . ?
C6 C1 C7 110.33(10) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.93(13) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.50(12) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.60(13) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.11(12) . . ?
C6 C5 H5 121.4 . . ?
C1 C6 N1 109.61(10) . . ?
C5 C6 N1 128.30(11) . . ?
C5 C6 C1 122.05(11) . . ?
C1 C7 H7A 111.0 . . ?
C1 C7 H7B 111.0 . . ?
C1 C7 C8 103.62(9) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
N1 C8 C7 103.88(9) . . ?
N1 C8 H8 110.2 . . ?
N1 C8 C9 110.64(9) . . ?
C7 C8 H8 110.2 . . ?
C9 C8 C7 111.62(9) . . ?
C9 C8 H8 110.2 . . ?
C10 C9 C8 124.89(11) . . ?
C10 C9 C11 118.59(11) . . ?
C11 C9 C8 116.49(10) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
O3 C11 C9 110.80(10) . . ?
O4 C11 O3 123.56(12) . . ?
O4 C11 C9 125.64(12) . . ?
O3 C12 H12A 110.4 . . ?
O3 C12 H12B 110.4 . . ?
O3 C12 C13 106.79(11) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 S1 119.11(9) . . ?
C19 C14 S1 119.60(9) . . ?
C19 C14 C15 121.29(11) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.75(11) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.39(12) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.33(12) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.20(12) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 120.5 . . ?
C18 C19 C14 119.04(12) . . ?
C18 C19 H19 120.5 . . ?

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 C6 C1 -144.37(9) . . . . ?
S1 N1 C6 C5 38.22(16) . . . . ?
S1 N1 C8 C7 136.87(8) . . . . ?
S1 N1 C8 C9 -103.23(10) . . . . ?
S1 C14 C15 C16 -179.43(9) . . . . ?
S1 C14 C19 C18 -179.76(9) . . . . ?
O1 S1 N1 C6 -47.23(10) . . . . ?
O1 S1 N1 C8 164.90(8) . . . . ?
O1 S1 C14 C15 -167.93(9) . . . . ?
O1 S1 C14 C19 12.11(11) . . . . ?
O2 S1 N1 C6 -176.74(9) . . . . ?
O2 S1 N1 C8 35.39(9) . . . . ?
O2 S1 C14 C15 -36.34(11) . . . . ?
O2 S1 C14 C19 143.69(9) . . . . ?
N1 S1 C14 C15 76.89(10) . . . . ?
N1 S1 C14 C19 -103.08(10) . . . . ?
N1 C8 C9 C10 -9.52(16) . . . . ?
N1 C8 C9 C11 172.38(9) . . . . ?
C1 C2 C3 C4 -0.29(19) . . . . ?
C1 C7 C8 N1 17.59(11) . . . . ?
C1 C7 C8 C9 -101.65(11) . . . . ?
C2 C1 C6 N1 -175.99(10) . . . . ?
C2 C1 C6 C5 1.61(17) . . . . ?
C2 C1 C7 C8 167.16(12) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -0.23(18) . . . . ?
C4 C5 C6 N1 176.11(11) . . . . ?
C4 C5 C6 C1 -1.01(17) . . . . ?
C6 N1 C8 C7 -15.18(11) . . . . ?
C6 N1 C8 C9 104.72(10) . . . . ?
C6 C1 C2 C3 -0.92(18) . . . . ?
C6 C1 C7 C8 -14.83(13) . . . . ?
C7 C1 C2 C3 176.92(12) . . . . ?
C7 C1 C6 N1 5.77(13) . . . . ?
C7 C1 C6 C5 -176.63(11) . . . . ?
C7 C8 C9 C10 105.63(13) . . . . ?
C7 C8 C9 C11 -72.47(13) . . . . ?
C8 N1 C6 C1 6.43(12) . . . . ?
C8 N1 C6 C5 -170.98(11) . . . . ?
C8 C9 C11 O3 -1.65(14) . . . . ?
C8 C9 C11 O4 178.05(11) . . . . ?
C10 C9 C11 O3 -179.87(11) . . . . ?
C10 C9 C11 O4 -0.17(19) . . . . ?
C11 O3 C12 C13 -178.44(10) . . . . ?
C12 O3 C11 O4 -0.08(17) . . . . ?
C12 O3 C11 C9 179.62(10) . . . . ?
C14 S1 N1 C6 68.19(10) . . . . ?
C14 S1 N1 C8 -79.68(9) . . . . ?
C14 C15 C16 C17 -0.72(18) . . . . ?
C15 C14 C19 C18 0.27(18) . . . . ?
C15 C16 C17 C18 0.09(19) . . . . ?
C16 C17 C18 C19 0.7(2) . . . . ?
C17 C18 C19 C14 -0.91(19) . . . . ?
C19 C14 C15 C16 0.54(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.518
_oxdiff_exptl_absorpt_empirical_full_min 0.827
####################################################################### 
# 
# 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_lsh-87
_database_code_depnum_ccdc_archive 'CCDC 2293949'
loop_
_audit_author_name
_audit_author_address
'Nengzhong Wang'
;China Three Gorges University
China
;
_audit_update_record             
;
2023-09-09 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-09-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H29 N O4 S2'
_chemical_formula_sum            'C27 H29 N O4 S2'
_chemical_formula_weight         495.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.24180(10)
_cell_length_b                   19.5215(3)
_cell_length_c                   14.0366(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.178(2)
_cell_angle_gamma                90
_cell_volume                     2499.98(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5512
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      73.4210
_cell_measurement_theta_min      4.5270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.16
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13621
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.432
_diffrn_reflns_theta_min         3.912
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  28.00   0.50    0.50    --    0.00 -82.00 -60.00  122
  2  ω    -33.00  20.00   0.50    0.50    --    0.00 -82.00-150.00  106
  3  ω    -28.00  12.00   0.50    0.50    --    0.00 -82.00  60.00   80
  4  ω    -31.00  -6.00   0.50    0.50    --    0.00 -82.00  30.00   50
  5  ω     71.00  97.00   0.50    0.80    --   95.80 -45.00  60.00   52
  6  ω      6.00 119.00   0.50    0.80    --   95.80 -61.00  30.00  226
  7  ω     79.00 121.00   0.50    0.80    --   95.80  30.00-180.00   84
  8  ω      6.00  67.00   0.50    0.80    --   95.80 -45.00  60.00  122
  9  ω     54.00  98.00   0.50    0.80    --   95.80 -30.00 150.00   88
 10  ω      6.00 127.00   0.50    0.80    --   95.80 -82.00  30.00  242
 11  ω     73.00 134.00   0.50    0.80    --   95.80  61.00-180.00  122
 12  ω     83.00 173.00   0.50    0.80    --   95.80  30.00-120.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0159102000
_diffrn_orient_matrix_UB_12      0.0065130000
_diffrn_orient_matrix_UB_13      -0.1105695000
_diffrn_orient_matrix_UB_21      0.0401946000
_diffrn_orient_matrix_UB_22      0.0764894000
_diffrn_orient_matrix_UB_23      0.0105428000
_diffrn_orient_matrix_UB_31      0.1632127000
_diffrn_orient_matrix_UB_32      -0.0183144000
_diffrn_orient_matrix_UB_33      0.0049832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4124
_reflns_number_total             4968
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.096
_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)+(0.0543P)²+1.0073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1248
_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 Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16),
 C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_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 0.34567(5) 0.63073(3) 0.53436(4) 0.02835(14) Uani 1 1 d . . . . .
S2 S 0.35270(7) 0.58036(3) 0.91827(4) 0.03810(16) Uani 1 1 d . . . . .
O1 O 0.36557(15) 0.70329(7) 0.53943(11) 0.0326(4) Uani 1 1 d . . . . .
O2 O 0.46375(15) 0.58615(7) 0.57273(12) 0.0330(4) Uani 1 1 d . . . . .
O3 O 0.36882(17) 0.41864(7) 0.73241(12) 0.0358(4) Uani 1 1 d . . . . .
O4 O 0.18458(18) 0.43869(8) 0.81479(11) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.21286(17) 0.61285(8) 0.59567(13) 0.0281(4) Uani 1 1 d . . . . .
C1 C -0.0367(2) 0.60175(10) 0.59433(14) 0.0249(4) Uani 1 1 d . . . . .
C2 C -0.1802(2) 0.62450(11) 0.58473(15) 0.0286(4) Uani 1 1 d . . . . .
H2 H -0.256357 0.594213 0.595536 0.034 Uiso 1 1 calc R U . . .
C3 C -0.2111(2) 0.69239(12) 0.55902(15) 0.0313(5) Uani 1 1 d . . . . .
H3 H -0.309315 0.708419 0.551663 0.038 Uiso 1 1 calc R U . . .
C4 C -0.0998(2) 0.73693(11) 0.54401(15) 0.0290(4) Uani 1 1 d . . . . .
H4 H -0.122719 0.783171 0.526668 0.035 Uiso 1 1 calc R U . . .
C5 C 0.0450(2) 0.71473(10) 0.55405(14) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.121623 0.745129 0.544409 0.033 Uiso 1 1 calc R U . . .
C6 C 0.0736(2) 0.64665(10) 0.57863(14) 0.0247(4) Uani 1 1 d . . . . .
C7 C 0.0256(2) 0.53218(11) 0.62401(17) 0.0308(5) Uani 1 1 d . . . . .
H7A H -0.013535 0.496956 0.575993 0.037 Uiso 1 1 calc R U . . .
H7B H 0.001765 0.518890 0.687781 0.037 Uiso 1 1 calc R U . . .
C8 C 0.1931(2) 0.54050(10) 0.62856(15) 0.0263(4) Uani 1 1 d . . . . .
H8 H 0.228950 0.507599 0.582951 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2822(2) 0.53139(10) 0.73050(15) 0.0257(4) Uani 1 1 d . . . . .
H9 H 0.387484 0.540851 0.726858 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2335(2) 0.58081(11) 0.80371(17) 0.0337(5) Uani 1 1 d . . . . .
H10A H 0.133181 0.568392 0.813827 0.040 Uiso 1 1 calc R U . . .
H10B H 0.229723 0.627784 0.776825 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5185(2) 0.61560(11) 0.89219(15) 0.0314(5) Uani 1 1 d . . . . .
C12 C 0.5320(2) 0.65294(11) 0.80953(15) 0.0306(5) Uani 1 1 d . . . . .
H12 H 0.448600 0.660994 0.761840 0.037 Uiso 1 1 calc R U . . .
C13 C 0.6683(2) 0.67833(11) 0.79730(16) 0.0321(5) Uani 1 1 d . . . . .
H13 H 0.676769 0.702855 0.739997 0.039 Uiso 1 1 calc R U . . .
C14 C 0.7926(2) 0.66902(11) 0.86617(16) 0.0336(5) Uani 1 1 d . . . . .
C15 C 0.6426(3) 0.60522(12) 0.96144(16) 0.0366(5) Uani 1 1 d . . . . .
H15 H 0.635258 0.579063 1.017543 0.044 Uiso 1 1 calc R U . . .
C16 C 0.7758(3) 0.63269(11) 0.94903(17) 0.0381(5) Uani 1 1 d . . . . .
H16 H 0.858162 0.626661 0.998249 0.046 Uiso 1 1 calc R U . . .
C17 C 0.9371(3) 0.69903(13) 0.8521(2) 0.0437(6) Uani 1 1 d . . . . .
H17A H 0.949628 0.694008 0.784464 0.066 Uiso 1 1 calc R U . . .
H17B H 1.016523 0.674969 0.893503 0.066 Uiso 1 1 calc R U . . .
H17C H 0.939627 0.747730 0.869287 0.066 Uiso 1 1 calc R U . . .
C18 C 0.2702(2) 0.45835(10) 0.76444(15) 0.0266(4) Uani 1 1 d . . . . .
C19 C 0.3781(3) 0.34800(11) 0.76620(19) 0.0398(6) Uani 1 1 d . . . . .
H19A H 0.366372 0.346827 0.835061 0.048 Uiso 1 1 calc R U . . .
H19B H 0.476229 0.329427 0.760990 0.048 Uiso 1 1 calc R U . . .
C20 C 0.2633(3) 0.30392(13) 0.7092(2) 0.0457(6) Uani 1 1 d . . . . .
H20A H 0.272583 0.306167 0.640701 0.069 Uiso 1 1 calc R U . . .
H20B H 0.165967 0.320259 0.717892 0.069 Uiso 1 1 calc R U . . .
H20C H 0.276034 0.256450 0.731687 0.069 Uiso 1 1 calc R U . . .
C21 C 0.2868(2) 0.60772(10) 0.41348(16) 0.0283(4) Uani 1 1 d . . . . .
C22 C 0.3383(2) 0.54804(11) 0.37702(18) 0.0338(5) Uani 1 1 d . . . . .
H22 H 0.404792 0.519408 0.417568 0.041 Uiso 1 1 calc R U . . .
C23 C 0.2926(2) 0.53018(11) 0.28145(18) 0.0350(5) Uani 1 1 d . . . . .
H23 H 0.328737 0.489322 0.256947 0.042 Uiso 1 1 calc R U . . .
C24 C 0.1949(2) 0.57105(11) 0.22077(17) 0.0335(5) Uani 1 1 d . . . . .
C25 C 0.1443(2) 0.63108(12) 0.25869(16) 0.0342(5) Uani 1 1 d . . . . .
H25 H 0.077681 0.659637 0.218134 0.041 Uiso 1 1 calc R U . . .
C26 C 0.1890(2) 0.64990(11) 0.35375(17) 0.0320(5) Uani 1 1 d . . . . .
H26 H 0.153682 0.690953 0.378213 0.038 Uiso 1 1 calc R U . . .
C27 C 0.1441(3) 0.55148(14) 0.11734(18) 0.0438(6) Uani 1 1 d . . . . .
H27A H 0.043482 0.534020 0.110135 0.066 Uiso 1 1 calc R U . . .
H27B H 0.208563 0.515871 0.098344 0.066 Uiso 1 1 calc R U . . .
H27C H 0.146977 0.591783 0.076061 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4287(15) . ?
S1 O2 1.4319(14) . ?
S1 N1 1.6450(18) . ?
S1 C21 1.756(2) . ?
S2 C10 1.799(2) . ?
S2 C11 1.771(2) . ?
O3 C18 1.328(3) . ?
O3 C19 1.456(3) . ?
O4 C18 1.204(3) . ?
N1 C6 1.432(2) . ?
N1 C8 1.506(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.388(3) . ?
C1 C7 1.508(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.548(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.543(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.529(3) . ?
C9 C18 1.513(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.393(3) . ?
C11 C15 1.394(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(3) . ?
C14 C16 1.392(3) . ?
C14 C17 1.500(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.495(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.387(3) . ?
C21 C26 1.399(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(3) . ?
C24 C25 1.398(3) . ?
C24 C27 1.502(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(3) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.96(9) . . ?
O1 S1 N1 106.57(9) . . ?
O1 S1 C21 108.62(9) . . ?
O2 S1 N1 105.18(9) . . ?
O2 S1 C21 107.95(10) . . ?
N1 S1 C21 108.03(9) . . ?
C11 S2 C10 103.91(11) . . ?
C18 O3 C19 116.76(18) . . ?
C6 N1 S1 122.73(14) . . ?
C6 N1 C8 109.48(15) . . ?
C8 N1 S1 119.76(14) . . ?
C2 C1 C6 119.86(19) . . ?
C2 C1 C7 129.30(19) . . ?
C6 C1 C7 110.81(16) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.62(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.87(19) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.71(19) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 N1 110.22(17) . . ?
C5 C6 N1 127.79(18) . . ?
C5 C6 C1 121.94(18) . . ?
C1 C7 H7A 110.8 . . ?
C1 C7 H7B 110.8 . . ?
C1 C7 C8 104.60(16) . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
N1 C8 C7 104.78(15) . . ?
N1 C8 H8 109.7 . . ?
N1 C8 C9 108.64(15) . . ?
C7 C8 H8 109.7 . . ?
C9 C8 C7 114.10(17) . . ?
C9 C8 H8 109.7 . . ?
C8 C9 H9 108.1 . . ?
C10 C9 C8 112.32(17) . . ?
C10 C9 H9 108.1 . . ?
C18 C9 C8 110.23(16) . . ?
C18 C9 H9 108.1 . . ?
C18 C9 C10 109.81(17) . . ?
S2 C10 H10A 108.9 . . ?
S2 C10 H10B 108.9 . . ?
C9 C10 S2 113.19(15) . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 S2 124.82(17) . . ?
C12 C11 C15 118.9(2) . . ?
C15 C11 S2 116.23(18) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.1(2) . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C16 117.3(2) . . ?
C13 C14 C17 120.8(2) . . ?
C16 C14 C17 121.9(2) . . ?
C11 C15 H15 119.8 . . ?
C16 C15 C11 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C16 H16 119.2 . . ?
C15 C16 C14 121.6(2) . . ?
C15 C16 H16 119.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 C9 110.77(18) . . ?
O4 C18 O3 124.27(19) . . ?
O4 C18 C9 124.95(19) . . ?
O3 C19 H19A 109.3 . . ?
O3 C19 H19B 109.3 . . ?
O3 C19 C20 111.76(19) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 S1 120.00(16) . . ?
C22 C21 C26 120.0(2) . . ?
C26 C21 S1 119.98(17) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.1(2) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 118.1(2) . . ?
C23 C24 C27 121.2(2) . . ?
C25 C24 C27 120.6(2) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 C24 121.6(2) . . ?
C26 C25 H25 119.2 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.2(2) . . ?
C25 C26 H26 120.4 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 C6 C1 146.47(15) . . . . ?
S1 N1 C6 C5 -36.2(3) . . . . ?
S1 N1 C8 C7 -146.37(15) . . . . ?
S1 N1 C8 C9 91.31(19) . . . . ?
S1 C21 C22 C23 -179.53(16) . . . . ?
S1 C21 C26 C25 179.75(17) . . . . ?
S2 C11 C12 C13 179.71(17) . . . . ?
S2 C11 C15 C16 -177.85(18) . . . . ?
O1 S1 N1 C6 51.91(18) . . . . ?
O1 S1 N1 C8 -162.59(14) . . . . ?
O1 S1 C21 C22 141.55(17) . . . . ?
O1 S1 C21 C26 -37.92(19) . . . . ?
O2 S1 N1 C6 -179.73(16) . . . . ?
O2 S1 N1 C8 -34.23(17) . . . . ?
O2 S1 C21 C22 10.0(2) . . . . ?
O2 S1 C21 C26 -169.46(16) . . . . ?
N1 S1 C21 C22 -103.23(18) . . . . ?
N1 S1 C21 C26 77.29(18) . . . . ?
N1 C8 C9 C10 59.6(2) . . . . ?
N1 C8 C9 C18 -177.65(16) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C7 C8 N1 -3.2(2) . . . . ?
C1 C7 C8 C9 115.54(19) . . . . ?
C2 C1 C6 N1 178.06(18) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C7 C8 -175.8(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 N1 -178.0(2) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C6 N1 C8 C7 3.3(2) . . . . ?
C6 N1 C8 C9 -119.05(18) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C1 C7 C8 2.1(2) . . . . ?
C7 C1 C2 C3 178.0(2) . . . . ?
C7 C1 C6 N1 -0.1(2) . . . . ?
C7 C1 C6 C5 -177.58(19) . . . . ?
C7 C8 C9 C10 -56.9(2) . . . . ?
C7 C8 C9 C18 65.9(2) . . . . ?
C8 N1 C6 C1 -2.1(2) . . . . ?
C8 N1 C6 C5 175.2(2) . . . . ?
C8 C9 C10 S2 -171.17(14) . . . . ?
C8 C9 C18 O3 85.0(2) . . . . ?
C8 C9 C18 O4 -95.9(2) . . . . ?
C10 S2 C11 C12 17.2(2) . . . . ?
C10 S2 C11 C15 -163.76(17) . . . . ?
C10 C9 C18 O3 -150.69(17) . . . . ?
C10 C9 C18 O4 28.3(3) . . . . ?
C11 S2 C10 C9 67.21(17) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C11 C15 C16 C14 -2.6(4) . . . . ?
C12 C11 C15 C16 1.3(3) . . . . ?
C12 C13 C14 C16 0.1(3) . . . . ?
C12 C13 C14 C17 -178.0(2) . . . . ?
C13 C14 C16 C15 1.8(3) . . . . ?
C15 C11 C12 C13 0.7(3) . . . . ?
C17 C14 C16 C15 180.0(2) . . . . ?
C18 O3 C19 C20 81.9(3) . . . . ?
C18 C9 C10 S2 65.80(19) . . . . ?
C19 O3 C18 O4 -4.0(3) . . . . ?
C19 O3 C18 C9 175.04(17) . . . . ?
C21 S1 N1 C6 -64.65(18) . . . . ?
C21 S1 N1 C8 80.85(16) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C22 C23 C24 C27 -179.4(2) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C26 C21 C22 C23 0.0(3) . . . . ?
C27 C24 C25 C26 179.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.742
_oxdiff_exptl_absorpt_empirical_full_min 0.541
####################################################################### 
# 
# 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_lsh-130
_database_code_depnum_ccdc_archive 'CCDC 2325027'
loop_
_audit_author_name
_audit_author_address
'Nengzhong Wang'
;China Three Gorges University
China
;
_audit_update_record             
;
2024-01-12 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_audit_creation_date             2024-01-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O5 S'
_chemical_formula_sum            'C20 H21 N O5 S'
_chemical_formula_weight         387.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N  S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0093(9)
_cell_length_b                   9.9303(10)
_cell_length_c                   13.0524(6)
_cell_angle_alpha                92.274(6)
_cell_angle_beta                 107.728(8)
_cell_angle_gamma                106.033(10)
_cell_volume                     941.63(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3513
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      73.5200
_cell_measurement_theta_min      3.5840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7837
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.073
_diffrn_reflns_theta_min         3.588
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  12.00   0.50    0.50    --    0.00 -82.00  30.00   52
  2  ω    -45.00   3.00   0.50    0.50    --    0.00 -77.00  60.00   96
  3  ω    -33.00  26.00   0.50    0.50    --    0.00 -82.00 -60.00  118
  4  ω    -29.00  15.00   0.50    0.50    --    0.00 -82.00-180.00   88
  5  ω    -27.00  21.00   0.50    0.50    --    0.00 -82.00 120.00   96
  6  ω     -6.00  19.00   0.50    0.50    --    0.00 -82.00-120.00   50
  7  ω      6.00  32.00   0.50    0.50    --   95.80 -82.00-150.00   52
  8  ω     14.00 112.00   0.50    0.50    --   95.80 -30.00-180.00  196
  9  ω     34.00  70.00   0.50    0.50    --   95.80 -77.00-120.00   72
 10  ω      7.00  93.00   0.50    0.50    --   95.80 -61.00 -30.00  172
 11  ω     14.00 107.00   0.50    0.50    --   95.80 -61.00  60.00  186
 12  ω     53.00 117.00   0.50    0.50    --   95.80 -82.00-180.00  128
 13  ω      8.00 106.00   0.50    0.50    --   95.80 -30.00  90.00  196
 14  ω     45.00  75.00   0.50    0.50    --   95.80 -82.00-150.00   60
 15  ω      9.00  34.00   0.50    0.50    --   95.80 -82.00-180.00   50
 16  ω     79.00 173.00   0.50    0.50    --   95.80  15.00 -60.00  188
 17  ω     88.00 118.00   0.50    0.50    --   95.80 -82.00-150.00   60
 18  ω     28.00 123.00   0.50    0.50    --   95.80 -82.00 -30.00  190
 19  ω     24.00 118.00   0.50    0.50    --   95.80 -82.00  60.00  188
 20  ω     93.00 118.00   0.50    0.50    --   95.80  82.00-180.00   50
 21  ω     97.00 122.00   0.50    0.50    --   95.80 -82.00-120.00   50
 22  ω    110.00 184.00   0.50    0.50    --   95.80   0.00  30.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1212996000
_diffrn_orient_matrix_UB_12      0.1393241000
_diffrn_orient_matrix_UB_13      -0.0204071000
_diffrn_orient_matrix_UB_21      0.0544561000
_diffrn_orient_matrix_UB_22      0.0603984000
_diffrn_orient_matrix_UB_23      0.1201411000
_diffrn_orient_matrix_UB_31      0.1649758000
_diffrn_orient_matrix_UB_32      -0.0590025000
_diffrn_orient_matrix_UB_33      0.0281083000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2948
_reflns_number_total             3580
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.017
_refine_diff_density_min         -1.269
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0793
_refine_ls_restrained_S_all      1.162
_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)+(0.1534P)²+0.7797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2277
_refine_ls_wR_factor_ref         0.2536
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.35549(11) 0.27417(9) 0.56809(6) 0.0262(3) Uani 1 1 d . . . . .
O1 O 0.2835(4) 0.3385(3) 0.47596(19) 0.0311(6) Uani 1 1 d . . . . .
O2 O 0.4709(3) 0.1877(3) 0.5653(2) 0.0303(6) Uani 1 1 d . . . . .
O3 O 0.3893(4) 0.3362(3) 0.8865(2) 0.0339(6) Uani 1 1 d . . . . .
H3 H 0.300119 0.367165 0.882204 0.051 Uiso 1 1 calc R U . . .
O4 O 0.8106(4) 0.2563(3) 0.9179(2) 0.0346(6) Uani 1 1 d . . . . .
O5 O 1.0751(4) 0.4083(3) 0.9158(2) 0.0427(7) Uani 1 1 d . . . . .
N1 N 0.4790(4) 0.4030(3) 0.6671(2) 0.0264(6) Uani 1 1 d . . . . .
C1 C 0.4549(5) 0.5491(4) 0.8016(3) 0.0261(7) Uani 1 1 d . . . . .
C2 C 0.4193(5) 0.6656(4) 0.8426(3) 0.0299(8) Uani 1 1 d . . . . .
H2 H 0.449924 0.689476 0.918627 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3386(5) 0.7460(4) 0.7709(3) 0.0324(8) Uani 1 1 d . . . . .
H3A H 0.312100 0.825059 0.797993 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2956(5) 0.7125(4) 0.6593(3) 0.0312(8) Uani 1 1 d . . . . .
H4 H 0.237291 0.767814 0.611375 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3368(5) 0.5990(4) 0.6166(3) 0.0286(8) Uani 1 1 d . . . . .
H5 H 0.311258 0.577578 0.540762 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4168(5) 0.5191(4) 0.6902(3) 0.0270(7) Uani 1 1 d . . . . .
C7 C 0.5273(5) 0.4392(4) 0.8592(3) 0.0285(8) Uani 1 1 d . . . . .
H7 H 0.636737 0.483826 0.925094 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5818(5) 0.3663(4) 0.7728(3) 0.0272(7) Uani 1 1 d . . . . .
H8 H 0.541520 0.261546 0.772375 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7896(5) 0.4191(4) 0.7937(3) 0.0306(8) Uani 1 1 d . . . . .
C10 C 0.9093(5) 0.3637(4) 0.8815(3) 0.0318(8) Uani 1 1 d . . . . .
C11 C 0.9128(7) 0.1931(5) 1.0048(4) 0.0478(11) Uani 1 1 d . . . . .
H11A H 0.963734 0.258395 1.073765 0.057 Uiso 1 1 calc R U . . .
H11B H 1.015814 0.173018 0.986954 0.057 Uiso 1 1 calc R U . . .
C12 C 0.7811(7) 0.0591(5) 1.0155(3) 0.0486(11) Uani 1 1 d . . . . .
H12A H 0.843801 0.015516 1.075551 0.073 Uiso 1 1 calc R U . . .
H12B H 0.735864 -0.006170 0.947906 0.073 Uiso 1 1 calc R U . . .
H12C H 0.677216 0.079962 1.030161 0.073 Uiso 1 1 calc R U . . .
C13 C 0.1715(5) 0.1764(4) 0.6072(3) 0.0268(7) Uani 1 1 d . . . . .
C14 C 0.1747(5) 0.0487(4) 0.6441(3) 0.0297(8) Uani 1 1 d . . . . .
H14 H 0.274312 0.012740 0.647719 0.036 Uiso 1 1 calc R U . . .
C15 C 0.0278(5) -0.0268(4) 0.6763(3) 0.0313(8) Uani 1 1 d . . . . .
H15 H 0.027386 -0.115273 0.701506 0.038 Uiso 1 1 calc R U . . .
C16 C -0.1174(5) 0.0264(4) 0.6719(3) 0.0322(8) Uani 1 1 d . . . . .
C17 C -0.1145(5) 0.1555(4) 0.6362(3) 0.0342(8) Uani 1 1 d . . . . .
H17 H -0.212351 0.192848 0.634360 0.041 Uiso 1 1 calc R U . . .
C18 C 0.0284(5) 0.2321(4) 0.6028(3) 0.0303(8) Uani 1 1 d . . . . .
H18 H 0.028472 0.320536 0.577496 0.036 Uiso 1 1 calc R U . . .
C19 C -0.2763(6) -0.0564(5) 0.7053(3) 0.0431(10) Uani 1 1 d . . . . .
H19A H -0.245013 -0.134829 0.741748 0.065 Uiso 1 1 calc R U . . .
H19B H -0.385549 -0.093934 0.640748 0.065 Uiso 1 1 calc R U . . .
H19C H -0.301477 0.005768 0.755016 0.065 Uiso 1 1 calc R U . . .
C20 C 0.8670(6) 0.5087(4) 0.7366(3) 0.0350(8) Uani 1 1 d . . . . .
H20A H 0.800(5) 0.550(4) 0.678(3) 0.026(9) Uiso 1 1 d . . . . .
H20B H 1.005(7) 0.540(5) 0.757(4) 0.045(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.424(3) . ?
S1 O2 1.431(2) . ?
S1 N1 1.636(3) . ?
S1 C13 1.756(4) . ?
O3 H3 0.8400 . ?
O3 C7 1.427(4) . ?
O4 C10 1.338(5) . ?
O4 C11 1.458(5) . ?
O5 C10 1.207(5) . ?
N1 C6 1.432(4) . ?
N1 C8 1.492(4) . ?
C1 C2 1.390(5) . ?
C1 C6 1.393(5) . ?
C1 C7 1.498(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(5) . ?
C3 H3A 0.9500 . ?
C3 C4 1.394(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.548(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.533(5) . ?
C9 C10 1.485(5) . ?
C9 C20 1.327(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.494(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.378(5) . ?
C13 C18 1.391(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(5) . ?
C16 C17 1.378(6) . ?
C16 C19 1.507(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(5) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.97(4) . ?
C20 H20B 1.01(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.84(15) . . ?
O1 S1 N1 106.48(15) . . ?
O1 S1 C13 108.35(16) . . ?
O2 S1 N1 105.62(15) . . ?
O2 S1 C13 108.38(16) . . ?
N1 S1 C13 106.28(15) . . ?
C7 O3 H3 109.5 . . ?
C10 O4 C11 116.8(3) . . ?
C6 N1 S1 122.6(2) . . ?
C6 N1 C8 107.7(3) . . ?
C8 N1 S1 118.1(2) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 C7 130.0(3) . . ?
C6 C1 C7 110.1(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3A 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 121.6 . . ?
C6 C5 C4 116.9(3) . . ?
C6 C5 H5 121.6 . . ?
C1 C6 N1 110.4(3) . . ?
C5 C6 N1 127.3(3) . . ?
C5 C6 C1 122.2(3) . . ?
O3 C7 C1 112.2(3) . . ?
O3 C7 H7 111.0 . . ?
O3 C7 C8 108.6(3) . . ?
C1 C7 H7 111.0 . . ?
C1 C7 C8 102.8(3) . . ?
C8 C7 H7 111.0 . . ?
N1 C8 C7 105.1(3) . . ?
N1 C8 H8 109.7 . . ?
N1 C8 C9 110.8(3) . . ?
C7 C8 H8 109.7 . . ?
C9 C8 C7 111.7(3) . . ?
C9 C8 H8 109.7 . . ?
C10 C9 C8 117.6(3) . . ?
C20 C9 C8 123.7(3) . . ?
C20 C9 C10 118.7(4) . . ?
O4 C10 C9 111.6(3) . . ?
O5 C10 O4 123.7(4) . . ?
O5 C10 C9 124.8(4) . . ?
O4 C11 H11A 110.3 . . ?
O4 C11 H11B 110.3 . . ?
O4 C11 C12 107.1(4) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 S1 119.4(3) . . ?
C14 C13 C18 121.7(3) . . ?
C18 C13 S1 118.9(3) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.5(3) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C19 120.5(4) . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 C19 120.4(4) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 120.8 . . ?
C17 C18 C13 118.4(3) . . ?
C17 C18 H18 120.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20A 124(2) . . ?
C9 C20 H20B 119(3) . . ?
H20A C20 H20B 117(4) . . ?

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 C6 C1 136.1(3) . . . . ?
S1 N1 C6 C5 -46.7(5) . . . . ?
S1 N1 C8 C7 -128.2(3) . . . . ?
S1 N1 C8 C9 111.0(3) . . . . ?
S1 C13 C14 C15 179.1(3) . . . . ?
S1 C13 C18 C17 -178.6(3) . . . . ?
O1 S1 N1 C6 45.1(3) . . . . ?
O1 S1 N1 C8 -176.2(2) . . . . ?
O1 S1 C13 C14 142.4(3) . . . . ?
O1 S1 C13 C18 -39.4(3) . . . . ?
O2 S1 N1 C6 174.7(2) . . . . ?
O2 S1 N1 C8 -46.5(3) . . . . ?
O2 S1 C13 C14 9.6(3) . . . . ?
O2 S1 C13 C18 -172.2(3) . . . . ?
O3 C7 C8 N1 99.8(3) . . . . ?
O3 C7 C8 C9 -140.0(3) . . . . ?
N1 S1 C13 C14 -103.5(3) . . . . ?
N1 S1 C13 C18 74.7(3) . . . . ?
N1 C8 C9 C10 -166.2(3) . . . . ?
N1 C8 C9 C20 12.5(5) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C1 C7 C8 N1 -19.2(3) . . . . ?
C1 C7 C8 C9 101.0(3) . . . . ?
C2 C1 C6 N1 174.8(3) . . . . ?
C2 C1 C6 C5 -2.5(5) . . . . ?
C2 C1 C7 O3 77.9(5) . . . . ?
C2 C1 C7 C8 -165.6(4) . . . . ?
C2 C3 C4 C5 -1.6(6) . . . . ?
C3 C4 C5 C6 2.0(5) . . . . ?
C4 C5 C6 N1 -176.8(3) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C6 N1 C8 C7 16.1(3) . . . . ?
C6 N1 C8 C9 -104.7(3) . . . . ?
C6 C1 C2 C3 2.9(5) . . . . ?
C6 C1 C7 O3 -100.1(3) . . . . ?
C6 C1 C7 C8 16.3(4) . . . . ?
C7 C1 C2 C3 -175.0(4) . . . . ?
C7 C1 C6 N1 -6.9(4) . . . . ?
C7 C1 C6 C5 175.8(3) . . . . ?
C7 C8 C9 C10 77.0(4) . . . . ?
C7 C8 C9 C20 -104.4(4) . . . . ?
C8 N1 C6 C1 -6.2(4) . . . . ?
C8 N1 C6 C5 170.9(3) . . . . ?
C8 C9 C10 O4 10.2(4) . . . . ?
C8 C9 C10 O5 -170.4(4) . . . . ?
C10 O4 C11 C12 -168.2(3) . . . . ?
C11 O4 C10 O5 0.8(5) . . . . ?
C11 O4 C10 C9 -179.7(3) . . . . ?
C13 S1 N1 C6 -70.3(3) . . . . ?
C13 S1 N1 C8 68.5(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C13 C18 C17 -0.4(5) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C14 C15 C16 C19 179.2(3) . . . . ?
C15 C16 C17 C18 1.2(6) . . . . ?
C16 C17 C18 C13 -0.7(6) . . . . ?
C18 C13 C14 C15 1.0(5) . . . . ?
C19 C16 C17 C18 -178.6(3) . . . . ?
C20 C9 C10 O4 -168.6(3) . . . . ?
C20 C9 C10 O5 10.8(6) . . . . ?

_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 1.986
_oxdiff_exptl_absorpt_empirical_full_min 0.617
