# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_exp_6352_auto
_database_code_depnum_ccdc_archive 'CCDC 2105071'
loop_
_audit_author_name
_audit_author_address
'shaonan zhang'
;shaonan zhang
China
;
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-08-24
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N O5 S'
_chemical_formula_sum            'C24 H21 N O5 S'
_chemical_formula_weight         435.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N S H'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.51370(10)
_cell_length_b                   14.8988(2)
_cell_length_c                   15.9015(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2017.01(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7393
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      75.0530
_cell_measurement_theta_min      4.0610
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
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    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10555
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.253
_diffrn_reflns_theta_min         4.066
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -12.00   0.50    0.80    --  -42.97 -78.00  26.00  198
  2  ω    -78.00 -23.00   0.50    3.20    --  -96.00  66.00 -79.00  110
  3  ω   -107.00 -31.00   0.50    3.20    --  -96.00  78.00  37.00  152
  4  ω   -113.00 -88.00   0.50    3.20    --  -96.00 -78.00  26.00   50
  5  ω   -167.00-120.00   0.50    3.20    --  -96.00 -78.00  26.00   94
  6  ω   -118.00 -73.00   0.50    0.80    --  -42.97-125.00  90.00   90
  7  ω   -118.00 -93.00   0.50    0.80    --  -42.97-125.00-180.00   50
  8  ω   -103.00 -77.00   0.50    0.80    --  -42.97-125.00   0.00   52
  9  ω     35.00  88.00   0.50    0.80    --   42.97-125.00-150.00  106
 10  ω    -49.00 -20.00   0.50    3.20    --  -96.00  45.00 -30.00   58
 11  ω    -48.00 -21.00   0.50    3.20    --  -96.00  45.00   0.00   54
 12  ω    124.00 150.00   0.50    3.20    --  109.46  77.00 -30.00   52
 13  ω     35.00  60.00   0.50    3.20    --  109.46 -61.00  60.00   50
 14  ω     81.00 176.00   0.50    3.20    --  109.46  30.00 120.00  190
 15  ω     63.00 107.00   0.50    3.20    --  109.46 -94.00-120.00   88
 16  ω     96.00 122.00   0.50    3.20    --  109.46  30.00-150.00   52
 17  ω     82.00 110.00   0.50    3.20    --  109.46  77.00 -30.00   56
 18  ω     35.00 101.00   0.50    3.20    --  109.46 -94.00  90.00  132
 19  ω     41.00  66.00   0.50    3.20    --  109.46 -61.00-180.00   50
 20  ω     46.00  71.00   0.50    3.20    --  109.46 -61.00 -90.00   50
 21  ω     38.00  73.00   0.50    3.20    --  109.46 -66.00 145.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1396873000
_diffrn_orient_matrix_UB_12      -0.0657038000
_diffrn_orient_matrix_UB_13      -0.0011835000
_diffrn_orient_matrix_UB_21      0.0634311000
_diffrn_orient_matrix_UB_22      -0.0423105000
_diffrn_orient_matrix_UB_23      -0.0816249000
_diffrn_orient_matrix_UB_31      0.0959395000
_diffrn_orient_matrix_UB_32      -0.0676997000
_diffrn_orient_matrix_UB_33      0.0521943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                3715
_reflns_number_total             3923
_reflns_odcompleteness_completeness 100.00
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3923
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.053
_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)+(0.0454P)²+0.0711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0743
_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:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C14(H14), C18(H18), C20(H20), C3(H3), C13(H13), C2(H2),
 C17(H17), C9(H9), C5(H5), C21(H21), C11(H11)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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 0.18086(6) 0.47410(4) 0.18503(3) 0.01544(13) Uani 1 1 d . . . . .
O1 O 0.02772(18) 0.50376(11) 0.46271(10) 0.0179(3) Uani 1 1 d . . . . .
O4 O 0.2547(2) 0.42139(12) 0.12210(10) 0.0216(4) Uani 1 1 d . . . . .
O5 O 0.01338(18) 0.48114(11) 0.18536(10) 0.0204(3) Uani 1 1 d . . . . .
O3 O -0.0198(2) 0.40715(13) 0.35776(11) 0.0244(4) Uani 1 1 d . . . . .
O2 O 0.24923(19) 0.57263(11) 0.17599(10) 0.0181(3) Uani 1 1 d . . . . .
N1 N 0.2560(2) 0.44742(13) 0.27565(11) 0.0153(4) Uani 1 1 d . . . . .
C1 C 0.1533(3) 0.66599(16) 0.38506(13) 0.0174(4) Uani 1 1 d . . . . .
H1 H 0.137472 0.647845 0.441710 0.021 Uiso 1 1 calc R U . . .
C4 C 0.1869(2) 0.60082(14) 0.32403(14) 0.0150(4) Uani 1 1 d . . . . .
C6 C 0.3518(2) 0.49729(15) 0.41296(13) 0.0150(4) Uani 1 1 d . . . . .
H6 H 0.314455 0.522240 0.467814 0.018 Uiso 1 1 calc R U . . .
C8 C 0.1926(3) 0.72079(16) 0.21966(14) 0.0199(5) Uani 1 1 d . . . . .
H8 H 0.203450 0.738603 0.162593 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4017(3) 0.40083(16) 0.42819(14) 0.0163(4) Uani 1 1 d . . . . .
C12 C 0.4917(3) 0.55366(16) 0.38456(13) 0.0170(4) Uani 1 1 d . . . . .
C14 C 0.1425(3) 0.75610(16) 0.36474(15) 0.0199(5) Uani 1 1 d . . . . .
H14 H 0.121859 0.799061 0.407487 0.024 Uiso 1 1 calc R U . . .
C16 C 0.0592(2) 0.46444(15) 0.38963(13) 0.0153(4) Uani 1 1 d . . . . .
C18 C 0.1619(3) 0.78399(16) 0.28165(15) 0.0212(5) Uani 1 1 d . . . . .
H18 H 0.154145 0.845807 0.267591 0.025 Uiso 1 1 calc R U . . .
C20 C 0.5236(3) 0.63495(17) 0.42416(15) 0.0214(5) Uani 1 1 d . . . . .
H20 H 0.457246 0.655021 0.468365 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2118(2) 0.50260(15) 0.34954(13) 0.0142(4) Uani 1 1 d . . . . .
C24 C 0.3780(3) 0.33429(16) 0.36842(14) 0.0181(5) Uani 1 1 d . . . . .
C3 C 0.4859(3) 0.38042(17) 0.50175(14) 0.0201(5) Uani 1 1 d . . . . .
H3 H 0.500212 0.425349 0.543442 0.024 Uiso 1 1 calc R U . . .
C13 C 0.5908(2) 0.52485(17) 0.32000(14) 0.0195(4) Uani 1 1 d . . . . .
H13 H 0.571137 0.469364 0.292521 0.023 Uiso 1 1 calc R U . . .
C7 C 0.2070(2) 0.63197(15) 0.24206(14) 0.0158(4) Uani 1 1 d . . . . .
C15 C -0.1286(2) 0.48507(17) 0.49830(14) 0.0209(5) Uani 1 1 d . . . . .
H15A H -0.145518 0.419515 0.502928 0.025 Uiso 1 1 calc R U . . .
H15B H -0.211543 0.510494 0.461709 0.025 Uiso 1 1 calc R U . . .
C2 C 0.4410(3) 0.24883(16) 0.38131(15) 0.0210(5) Uani 1 1 d . . . . .
H2 H 0.424550 0.203258 0.340453 0.025 Uiso 1 1 calc R U . . .
C17 C 0.7187(3) 0.57739(18) 0.29577(15) 0.0231(5) Uani 1 1 d . . . . .
H17 H 0.785665 0.557536 0.251747 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5272(3) 0.22980(17) 0.45310(15) 0.0242(5) Uani 1 1 d . . . . .
H9 H 0.571934 0.171952 0.460674 0.029 Uiso 1 1 calc R U . . .
C19 C 0.2863(3) 0.35084(16) 0.28876(14) 0.0203(5) Uani 1 1 d . . . . .
H19A H 0.345901 0.326901 0.240235 0.024 Uiso 1 1 calc R U . . .
H19B H 0.184983 0.318401 0.291770 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5479(3) 0.29598(17) 0.51416(15) 0.0234(5) Uani 1 1 d . . . . .
H5 H 0.604548 0.282902 0.564143 0.028 Uiso 1 1 calc R U . . .
C21 C 0.6513(3) 0.68729(17) 0.39990(17) 0.0261(5) Uani 1 1 d . . . . .
H21 H 0.671865 0.742700 0.427344 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7485(3) 0.65796(19) 0.33534(16) 0.0261(5) Uani 1 1 d . . . . .
H11 H 0.835596 0.693467 0.318418 0.031 Uiso 1 1 calc R U . . .
C23 C -0.1344(3) 0.5274(3) 0.58287(17) 0.0366(7) Uani 1 1 d . . . . .
H23A H -0.106316 0.590946 0.578206 0.055 Uiso 1 1 calc R U . . .
H23B H -0.059931 0.497059 0.620318 0.055 Uiso 1 1 calc R U . . .
H23C H -0.240786 0.521940 0.605862 0.055 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 O4 1.4190(17) . ?
S1 O5 1.4298(16) . ?
S1 O2 1.5857(16) . ?
S1 N1 1.6261(18) . ?
O1 C16 1.329(3) . ?
O1 C15 1.473(2) . ?
O3 C16 1.199(3) . ?
O2 C7 1.419(3) . ?
N1 C22 1.483(3) . ?
N1 C19 1.476(3) . ?
C1 H1 0.9500 . ?
C1 C4 1.402(3) . ?
C1 C14 1.384(3) . ?
C4 C22 1.533(3) . ?
C4 C7 1.394(3) . ?
C6 H6 1.0000 . ?
C6 C10 1.518(3) . ?
C6 C12 1.526(3) . ?
C6 C22 1.563(3) . ?
C8 H8 0.9500 . ?
C8 C18 1.388(3) . ?
C8 C7 1.376(3) . ?
C10 C24 1.388(3) . ?
C10 C3 1.405(3) . ?
C12 C20 1.392(3) . ?
C12 C13 1.397(3) . ?
C14 H14 0.9500 . ?
C14 C18 1.395(3) . ?
C16 C22 1.555(3) . ?
C18 H18 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.393(3) . ?
C24 C2 1.397(3) . ?
C24 C19 1.508(3) . ?
C3 H3 0.9500 . ?
C3 C5 1.378(4) . ?
C13 H13 0.9500 . ?
C13 C17 1.395(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C23 1.486(4) . ?
C2 H2 0.9500 . ?
C2 C9 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C11 1.379(4) . ?
C9 H9 0.9500 . ?
C9 C5 1.395(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C5 H5 0.9500 . ?
C21 H21 0.9500 . ?
C21 C11 1.389(4) . ?
C11 H11 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
O4 S1 O5 119.03(10) . . ?
O4 S1 O2 106.61(10) . . ?
O4 S1 N1 108.37(10) . . ?
O5 S1 O2 107.37(10) . . ?
O5 S1 N1 114.03(10) . . ?
O2 S1 N1 99.33(9) . . ?
C16 O1 C15 115.78(17) . . ?
C7 O2 S1 114.63(13) . . ?
C22 N1 S1 117.82(15) . . ?
C19 N1 S1 115.60(14) . . ?
C19 N1 C22 118.21(17) . . ?
C4 C1 H1 119.2 . . ?
C14 C1 H1 119.2 . . ?
C14 C1 C4 121.6(2) . . ?
C1 C4 C22 120.39(19) . . ?
C7 C4 C1 116.2(2) . . ?
C7 C4 C22 123.2(2) . . ?
C10 C6 H6 107.6 . . ?
C10 C6 C12 110.46(18) . . ?
C10 C6 C22 111.37(18) . . ?
C12 C6 H6 107.6 . . ?
C12 C6 C22 112.12(17) . . ?
C22 C6 H6 107.6 . . ?
C18 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C18 119.0(2) . . ?
C24 C10 C6 121.74(19) . . ?
C24 C10 C3 119.3(2) . . ?
C3 C10 C6 118.7(2) . . ?
C20 C12 C6 119.8(2) . . ?
C20 C12 C13 118.8(2) . . ?
C13 C12 C6 121.3(2) . . ?
C1 C14 H14 119.9 . . ?
C1 C14 C18 120.2(2) . . ?
C18 C14 H14 119.9 . . ?
O1 C16 C22 111.47(18) . . ?
O3 C16 O1 124.8(2) . . ?
O3 C16 C22 123.76(19) . . ?
C8 C18 C14 119.5(2) . . ?
C8 C18 H18 120.2 . . ?
C14 C18 H18 120.2 . . ?
C12 C20 H20 119.5 . . ?
C12 C20 C21 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
N1 C22 C4 110.77(17) . . ?
N1 C22 C6 106.83(16) . . ?
N1 C22 C16 109.54(17) . . ?
C4 C22 C6 108.92(17) . . ?
C4 C22 C16 110.00(17) . . ?
C16 C22 C6 110.73(17) . . ?
C10 C24 C2 119.7(2) . . ?
C10 C24 C19 122.3(2) . . ?
C2 C24 C19 118.1(2) . . ?
C10 C3 H3 119.6 . . ?
C5 C3 C10 120.8(2) . . ?
C5 C3 H3 119.6 . . ?
C12 C13 H13 119.9 . . ?
C17 C13 C12 120.1(2) . . ?
C17 C13 H13 119.9 . . ?
C4 C7 O2 121.0(2) . . ?
C8 C7 O2 115.47(19) . . ?
C8 C7 C4 123.5(2) . . ?
O1 C15 H15A 110.3 . . ?
O1 C15 H15B 110.3 . . ?
O1 C15 C23 107.30(19) . . ?
H15A C15 H15B 108.5 . . ?
C23 C15 H15A 110.3 . . ?
C23 C15 H15B 110.3 . . ?
C24 C2 H2 119.7 . . ?
C9 C2 C24 120.7(2) . . ?
C9 C2 H2 119.7 . . ?
C13 C17 H17 119.8 . . ?
C11 C17 C13 120.4(2) . . ?
C11 C17 H17 119.8 . . ?
C2 C9 H9 120.2 . . ?
C2 C9 C5 119.7(2) . . ?
C5 C9 H9 120.2 . . ?
N1 C19 C24 111.61(19) . . ?
N1 C19 H19A 109.3 . . ?
N1 C19 H19B 109.3 . . ?
C24 C19 H19A 109.3 . . ?
C24 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C3 C5 C9 119.8(2) . . ?
C3 C5 H5 120.1 . . ?
C9 C5 H5 120.1 . . ?
C20 C21 H21 120.2 . . ?
C11 C21 C20 119.6(2) . . ?
C11 C21 H21 120.2 . . ?
C17 C11 C21 120.1(2) . . ?
C17 C11 H11 119.9 . . ?
C21 C11 H11 119.9 . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
C15 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 O2 C7 C4 33.0(2) . . . . ?
S1 O2 C7 C8 -148.78(17) . . . . ?
S1 N1 C22 C4 -33.7(2) . . . . ?
S1 N1 C22 C6 -152.22(15) . . . . ?
S1 N1 C22 C16 87.8(2) . . . . ?
S1 N1 C19 C24 171.32(15) . . . . ?
O1 C16 C22 N1 171.07(16) . . . . ?
O1 C16 C22 C4 -66.9(2) . . . . ?
O1 C16 C22 C6 53.5(2) . . . . ?
O4 S1 O2 C7 -170.76(14) . . . . ?
O4 S1 N1 C22 172.02(16) . . . . ?
O4 S1 N1 C19 -40.25(19) . . . . ?
O5 S1 O2 C7 60.65(16) . . . . ?
O5 S1 N1 C22 -52.92(19) . . . . ?
O5 S1 N1 C19 94.81(17) . . . . ?
O3 C16 C22 N1 -9.4(3) . . . . ?
O3 C16 C22 C4 112.6(2) . . . . ?
O3 C16 C22 C6 -127.0(2) . . . . ?
O2 S1 N1 C22 60.94(17) . . . . ?
O2 S1 N1 C19 -151.33(16) . . . . ?
N1 S1 O2 C7 -58.28(16) . . . . ?
C1 C4 C22 N1 -176.25(19) . . . . ?
C1 C4 C22 C6 -59.0(3) . . . . ?
C1 C4 C22 C16 62.5(2) . . . . ?
C1 C4 C7 O2 176.80(19) . . . . ?
C1 C4 C7 C8 -1.2(3) . . . . ?
C1 C14 C18 C8 -0.2(3) . . . . ?
C4 C1 C14 C18 1.4(3) . . . . ?
C6 C10 C24 C2 173.1(2) . . . . ?
C6 C10 C24 C19 -6.6(3) . . . . ?
C6 C10 C3 C5 -173.2(2) . . . . ?
C6 C12 C20 C21 179.5(2) . . . . ?
C6 C12 C13 C17 -179.5(2) . . . . ?
C10 C6 C12 C20 -130.1(2) . . . . ?
C10 C6 C12 C13 49.0(3) . . . . ?
C10 C6 C22 N1 -49.8(2) . . . . ?
C10 C6 C22 C4 -169.52(17) . . . . ?
C10 C6 C22 C16 69.4(2) . . . . ?
C10 C24 C2 C9 -0.1(3) . . . . ?
C10 C24 C19 N1 11.5(3) . . . . ?
C10 C3 C5 C9 0.0(3) . . . . ?
C12 C6 C10 C24 -98.7(2) . . . . ?
C12 C6 C10 C3 75.9(2) . . . . ?
C12 C6 C22 N1 74.5(2) . . . . ?
C12 C6 C22 C4 -45.2(2) . . . . ?
C12 C6 C22 C16 -166.26(18) . . . . ?
C12 C20 C21 C11 -0.1(4) . . . . ?
C12 C13 C17 C11 0.1(3) . . . . ?
C14 C1 C4 C22 174.8(2) . . . . ?
C14 C1 C4 C7 -0.7(3) . . . . ?
C16 O1 C15 C23 174.5(2) . . . . ?
C18 C8 C7 O2 -175.8(2) . . . . ?
C18 C8 C7 C4 2.4(3) . . . . ?
C20 C12 C13 C17 -0.4(3) . . . . ?
C20 C21 C11 C17 -0.2(4) . . . . ?
C22 N1 C19 C24 -41.1(3) . . . . ?
C22 C4 C7 O2 1.4(3) . . . . ?
C22 C4 C7 C8 -176.6(2) . . . . ?
C22 C6 C10 C24 26.6(3) . . . . ?
C22 C6 C10 C3 -158.85(19) . . . . ?
C22 C6 C12 C20 105.1(2) . . . . ?
C22 C6 C12 C13 -75.8(3) . . . . ?
C24 C10 C3 C5 1.5(3) . . . . ?
C24 C2 C9 C5 1.7(3) . . . . ?
C3 C10 C24 C2 -1.5(3) . . . . ?
C3 C10 C24 C19 178.8(2) . . . . ?
C13 C12 C20 C21 0.4(3) . . . . ?
C13 C17 C11 C21 0.2(4) . . . . ?
C7 C4 C22 N1 -1.1(3) . . . . ?
C7 C4 C22 C6 116.1(2) . . . . ?
C7 C4 C22 C16 -122.3(2) . . . . ?
C7 C8 C18 C14 -1.6(3) . . . . ?
C15 O1 C16 O3 -10.5(3) . . . . ?
C15 O1 C16 C22 168.99(17) . . . . ?
C2 C24 C19 N1 -168.14(19) . . . . ?
C2 C9 C5 C3 -1.6(3) . . . . ?
C19 N1 C22 C4 179.38(18) . . . . ?
C19 N1 C22 C6 60.9(2) . . . . ?
C19 N1 C22 C16 -59.1(2) . . . . ?
C19 C24 C2 C9 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 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.623
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_zsn-5-134-6
_database_code_depnum_ccdc_archive 'CCDC 2105280'
loop_
_audit_author_name
_audit_author_address
'shaonan zhang'
;shaonan zhang
China
;
_audit_update_record             
;
2021-08-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2021-04-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H19 N O6 S'
_chemical_formula_sum            'C19 H19 N O6 S'
_chemical_formula_weight         389.41
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.4466(3)
_cell_length_b                   15.4504(6)
_cell_length_c                   15.8556(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1824.22(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2601
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.5730
_cell_measurement_theta_min      3.9760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.881
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22343
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.367
_diffrn_reflns_theta_min         3.995
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.881
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00 124.00   1.00    1.50    --   48.75 -19.00 150.00   86
  2  ω     45.00  82.00   1.00    1.75    --   97.50-112.00 120.00   37
  3  ω     32.00  57.00   1.00    1.00    --    0.00-178.00 150.00   25
  4  ω     38.00  73.00   1.00    1.00    --    0.00  57.00   0.00   35
  5  ω     73.00 120.00   1.00    1.50    --   48.75 125.00 -30.00   47
  6  ω     95.00 121.00   1.00    1.50    --   48.75  77.00 -30.00   26
  7  ω     74.00 115.00   1.00    1.50    --   48.75 125.00-120.00   41
  8  ω     85.00 111.00   1.00    1.75    --   97.50 178.00 -90.00   26
  9  ω     38.00  80.00   1.00    1.75    --   97.50 178.00 -90.00   42
 10  ω     12.00  39.00   1.00    1.50    --   48.75  77.00 -30.00   27
 11  ω     62.00 118.00   1.00    1.75    --   97.50  77.00-120.00   56
 12  ω    129.00 171.00   1.00    1.75    --   97.50  77.00-120.00   42
 13  ω     81.00 175.00   1.00    1.75    --   97.50 112.00  90.00   94
 14  ω     81.00 125.00   1.00    1.50    --   48.75 125.00 120.00   44
 15  ω     79.00 161.00   1.00    1.75    --   97.50 112.00 120.00   82
 16  ω     80.00 176.00   1.00    1.75    --   97.50 112.00 150.00   96
 17  ω     37.00  64.00   1.00    1.00    --    0.00 178.00  30.00   27
 18  ω     20.00 115.00   1.00    1.50    --   48.75  57.00 150.00   95
 19  ω    -30.00  32.00   1.00    1.00    --    0.00  57.00   0.00   62
 20  ω    -47.00 -21.00   1.00    1.50    --  -48.75 -57.00  60.00   26
 21  ω    -45.00  -9.00   1.00    1.50    --  -48.75 -84.00  50.31   36
 22  ω    -37.00  -5.00   1.00    1.50    --  -48.75 -90.00 -10.73   32
 23  ω    -47.00 -20.00   1.00    1.50    --  -48.75 -57.00 -90.00   27
 24  ω    -46.00  -9.00   1.00    1.50    --  -48.75 -83.00-143.80   37
 25  ω    -50.00 -12.00   1.00    1.50    --  -48.75 -77.00-120.00   38
 26  ω    -59.00  27.00   1.00    1.00    --    0.00 -57.00-150.00   86
 27  ω     28.00 125.00   1.00    1.75    --   97.50 -64.00-180.00   97
 28  ω    -35.00  -6.00   1.00    1.50    --  -48.75 -87.00 128.32   29
 29  ω    -48.00 -12.00   1.00    1.50    --  -48.75 -81.00 169.06   36
 30  ω    -91.00 -54.00   1.00    1.75    --  -92.00 -79.00 168.18   37
 31  ω    -87.00 -55.00   1.00    1.75    --  -92.00 -77.00 150.00   32
 32  ω    -94.00 -56.00   1.00    1.75    --  -92.00 -77.00  90.00   38
 33  ω    -91.00 -57.00   1.00    1.75    --  -92.00 -75.00  99.44   34
 34  ω    -96.00 -55.00   1.00    1.75    --  -92.00 -77.00 120.00   41
 35  ω   -108.00 -59.00   1.00    1.50    --  -48.75 -57.00  60.00   49
 36  ω    -80.00 -55.00   1.00    1.75    --  -92.00 -77.00   0.00   25
 37  ω    -83.00 -57.00   1.00    1.75    --  -92.00 -75.00 -77.79   26
 38  ω    -80.00 -55.00   1.00    1.75    --  -92.00 -77.00-120.00   25
 39  ω    -85.00 -56.00   1.00    1.75    --  -92.00 -77.00 -90.00   29
 40  ω    -94.00 -55.00   1.00    1.75    --  -92.00 -77.00-150.00   39
 41  ω    -91.00 -55.00   1.00    1.75    --  -92.00 -77.00-180.00   36
 42  ω   -106.00 -59.00   1.00    1.75    --  -92.00 -70.00-145.71   47
 43  ω   -115.00 -69.00   1.00    1.50    --  -48.75 -77.00-120.00   46
 44  ω   -113.00 -19.00   1.00    1.50    --  -48.75 -57.00 -30.00   94
 45  ω   -115.00 -55.00   1.00    1.75    --  -92.00 -77.00  30.00   60
 46  ω   -114.00 -62.00   1.00    1.75    --  -92.00 -64.00 -30.00   52
 47  ω   -121.00 -60.00   1.00    1.50    --  -48.75 -57.00 -90.00   61
 48  ω   -136.00 -56.00   1.00    1.75    --  -92.00 -76.00 -35.29   80
 49  ω   -140.00 -88.00   1.00    1.75    --  -92.00 -77.00-120.00   52
 50  ω   -139.00-105.00   1.00    1.75    --  -92.00 -77.00 -90.00   34
 51  ω   -159.00-104.00   1.00    1.75    --  -92.00 -77.00   0.00   55
 52  ω   -143.00-100.00   1.00    1.75    --  -92.00 -75.00  99.44   43
 53  ω   -152.00 -55.00   1.00    1.75    --  -92.00 -77.00 132.50   97
 54  ω   -148.00-122.00   1.00    1.75    --  -92.00 -77.00 150.00   26
 55  ω   -157.00 -54.00   1.00    1.75    --  -92.00 -79.00  81.15  103
 56  ω   -165.00 -55.00   1.00    1.75    --  -92.00 -77.00 -60.00  110
 57  ω   -166.00-140.00   1.00    1.75    --  -92.00 -75.00 -77.79   26
 58  ω   -163.00 -55.00   1.00    1.75    --  -92.00 -77.00  60.00  108
 59  ω    -68.00 -43.00   1.00    1.75    --  -92.00  77.00 150.00   25
 60  ω    -79.00 -25.00   1.00    1.50    --  -48.75 125.00  90.00   54
 61  ω    -59.00 -19.00   1.00    1.50    --  -48.75 125.00   0.00   40
 62  ω    -91.00 -66.00   1.00    1.75    --  -92.00 112.00 -30.00   25
 63  ω   -104.00 -69.00   1.00    1.75    --  -92.00 112.00 -90.00   35
 64  ω    -95.00 -28.00   1.00    1.50    --  -48.75 125.00-120.00   67
 65  ω   -101.00 -65.00   1.00    1.75    --  -92.00 112.00-180.00   36
 66  ω   -116.00 -14.00   1.00    1.75    --  -92.00 112.00 120.00  102
 67  ω   -124.00 -96.00   1.00    1.75    --  -92.00  77.00 150.00   28
 68  ω   -165.00-109.00   1.00    1.75    --  -92.00 -77.00 120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0509056000
_diffrn_orient_matrix_UB_12      -0.0713486000
_diffrn_orient_matrix_UB_13      -0.0635528000
_diffrn_orient_matrix_UB_21      -0.0561180000
_diffrn_orient_matrix_UB_22      0.0696523000
_diffrn_orient_matrix_UB_23      -0.0643269000
_diffrn_orient_matrix_UB_31      0.1924811000
_diffrn_orient_matrix_UB_32      0.0014693000
_diffrn_orient_matrix_UB_33      -0.0355528000
_diffrn_radiation_monochromator  mirror
_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 Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2548
_reflns_number_total             2867
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.176
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 974 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.029(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.112
_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)+(0.0529P)²+0.0948P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1037
_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:
 C7BA(H7BA,H7BB), C8BA(H8BA,H8BB), C9BA(H9BA,H9BB)
2.b Aromatic/amide H refined with riding coordinates:
 C4AA(H4AA), C5AA(H5AA), C7AA(H7AA), C2BA(H2BA), C5BA(H5BA), C1CA(H1CA), C1(H1)
2.c Idealised Me refined as rotating group:
 C0CA(H0CA,H0CB,H0CC), C(HA,HB,HC)
;
_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
S0AA S -0.12308(14) -0.96818(7) -0.40584(6) 0.0331(3) Uani 1 1 d . . . . .
O0AA O -0.6040(4) -0.87943(17) -0.41324(18) 0.0345(7) Uani 1 1 d . . . . .
O1 O -0.1266(4) -1.0060(2) -0.31259(17) 0.0396(7) Uani 1 1 d . . . . .
O2AA O 0.0524(4) -0.9858(2) -0.4355(2) 0.0440(8) Uani 1 1 d . . . . .
O1AA O -0.1884(4) -0.88222(19) -0.4032(2) 0.0417(8) Uani 1 1 d . . . . .
O O -0.7275(4) -1.2223(2) -0.3431(2) 0.0457(9) Uani 1 1 d . . . . .
O3AA O -0.5408(5) -0.9321(2) -0.54151(19) 0.0421(8) Uani 1 1 d . . . . .
C4AA C -0.6167(6) -1.0218(3) -0.2809(3) 0.0346(9) Uani 1 1 d . . . . .
H4AA H -0.7243 -1.0196 -0.3106 0.042 Uiso 1 1 calc R . . . .
C5AA C -0.6210(7) -1.0323(3) -0.1947(3) 0.0430(11) Uani 1 1 d . . . . .
H5AA H -0.7302 -1.0379 -0.1668 0.052 Uiso 1 1 calc R . . . .
C6AA C -0.4547(6) -1.0143(3) -0.3251(2) 0.0284(9) Uani 1 1 d . . . . .
C7AA C -0.4623(8) -1.0346(3) -0.1499(3) 0.0470(12) Uani 1 1 d . . . . .
H7AA H -0.4653 -1.0430 -0.0918 0.056 Uiso 1 1 calc R . . . .
C8AA C -0.5503(6) -1.2352(3) -0.3601(3) 0.0343(10) Uani 1 1 d . . . . .
C9AA C -0.4701(6) -1.1762(3) -0.4150(3) 0.0307(10) Uani 1 1 d . . . . .
C0BA C -0.5359(6) -0.9376(3) -0.4662(3) 0.0307(10) Uani 1 1 d . . . . .
C1BA C -0.3006(6) -1.0140(3) -0.2768(3) 0.0314(10) Uani 1 1 d . . . . .
C2BA C -0.1864(6) -1.2498(3) -0.3985(3) 0.0395(11) Uani 1 1 d . . . . .
H2BA H -0.0645 -1.2541 -0.4107 0.047 Uiso 1 1 calc R . . . .
C3BA C -0.2879(6) -1.1840(3) -0.4327(2) 0.0323(10) Uani 1 1 d . . . . .
N4BA N -0.2684(4) -1.0264(2) -0.4555(2) 0.0290(8) Uani 1 1 d . . . . .
C5BA C -0.2673(8) -1.3091(3) -0.3462(3) 0.0488(13) Uani 1 1 d . . . . .
H5BA H -0.2000 -1.3541 -0.3235 0.059 Uiso 1 1 calc R . . . .
C6BA C -0.4548(5) -1.0161(3) -0.4213(2) 0.0258(8) Uani 1 1 d . . . . .
C7BA C -0.2115(7) -1.1133(3) -0.4862(3) 0.0359(10) Uani 1 1 d . . . . .
H7BA H -0.0815 -1.1169 -0.4855 0.043 Uiso 1 1 calc R . . . .
H7BB H -0.2512 -1.1209 -0.5440 0.043 Uiso 1 1 calc R . . . .
C8BA C -0.5603(6) -1.0973(3) -0.4501(3) 0.0313(10) Uani 1 1 d . . . . .
H8BA H -0.6831 -1.0942 -0.4300 0.038 Uiso 1 1 calc R . . . .
H8BB H -0.5626 -1.1002 -0.5112 0.038 Uiso 1 1 calc R . . . .
C9BA C -0.6919(7) -0.8055(3) -0.4528(3) 0.0496(13) Uani 1 1 d . . . . .
H9BA H -0.7857 -0.8251 -0.4907 0.060 Uiso 1 1 calc R . . . .
H9BB H -0.6054 -0.7723 -0.4852 0.060 Uiso 1 1 calc R . . . .
C0CA C -0.7698(9) -0.7511(4) -0.3851(4) 0.0656(17) Uani 1 1 d . . . . .
H0CA H -0.8230 -0.7003 -0.4095 0.098 Uiso 1 1 calc GR . . . .
H0CB H -0.6769 -0.7343 -0.3465 0.098 Uiso 1 1 calc GR . . . .
H0CC H -0.8601 -0.7835 -0.3555 0.098 Uiso 1 1 calc GR . . . .
C1CA C -0.3006(7) -1.0247(3) -0.1897(3) 0.0427(11) Uani 1 1 d . . . . .
H1CA H -0.1937 -1.0252 -0.1594 0.051 Uiso 1 1 calc R . . . .
C C -0.7949(8) -1.2588(4) -0.2665(4) 0.0638(16) Uani 1 1 d . . . . .
HA H -0.8138 -1.3198 -0.2740 0.096 Uiso 1 1 calc GR . . . .
HB H -0.9066 -1.2315 -0.2521 0.096 Uiso 1 1 calc GR . . . .
HC H -0.7096 -1.2496 -0.2220 0.096 Uiso 1 1 calc GR . . . .
C1 C -0.4494(7) -1.3024(3) -0.3270(3) 0.0438(12) Uani 1 1 d . . . . .
H1 H -0.5032 -1.3431 -0.2919 0.053 Uiso 1 1 calc R . . . .


_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
S0AA O1 1.590(3) . ?
S0AA O2AA 1.416(3) . ?
S0AA O1AA 1.415(3) . ?
S0AA N4BA 1.612(4) . ?
O0AA C0BA 1.330(5) . ?
O0AA C9BA 1.459(5) . ?
O1 C1BA 1.420(5) . ?
O C8AA 1.362(6) . ?
O C 1.430(6) . ?
O3AA C0BA 1.198(5) . ?
C4AA C5AA 1.377(6) . ?
C4AA C6AA 1.400(6) . ?
C5AA C7AA 1.379(7) . ?
C6AA C1BA 1.380(6) . ?
C6AA C6BA 1.526(5) . ?
C7AA C1CA 1.368(7) . ?
C8AA C9AA 1.395(6) . ?
C8AA C1 1.385(7) . ?
C9AA C3BA 1.391(6) . ?
C9AA C8BA 1.498(6) . ?
C0BA C6BA 1.531(6) . ?
C1BA C1CA 1.391(6) . ?
C2BA C3BA 1.379(6) . ?
C2BA C5BA 1.375(7) . ?
C3BA C7BA 1.495(6) . ?
N4BA C6BA 1.498(5) . ?
N4BA C7BA 1.490(5) . ?
C5BA C1 1.393(7) . ?
C6BA C8BA 1.549(6) . ?
C9BA C0CA 1.481(7) . ?

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 S0AA N4BA 103.76(17) . . ?
O2AA S0AA O1 104.68(18) . . ?
O2AA S0AA N4BA 110.5(2) . . ?
O1AA S0AA O1 108.20(18) . . ?
O1AA S0AA O2AA 120.5(2) . . ?
O1AA S0AA N4BA 107.87(19) . . ?
C0BA O0AA C9BA 115.4(3) . . ?
C1BA O1 S0AA 114.8(3) . . ?
C8AA O C 116.8(4) . . ?
C5AA C4AA C6AA 121.8(4) . . ?
C4AA C5AA C7AA 119.6(5) . . ?
C4AA C6AA C6BA 119.9(4) . . ?
C1BA C6AA C4AA 116.0(4) . . ?
C1BA C6AA C6BA 123.8(4) . . ?
C1CA C7AA C5AA 120.9(4) . . ?
O C8AA C9AA 116.3(4) . . ?
O C8AA C1 124.1(4) . . ?
C1 C8AA C9AA 119.7(5) . . ?
C8AA C9AA C8BA 124.9(4) . . ?
C3BA C9AA C8AA 119.1(4) . . ?
C3BA C9AA C8BA 115.7(4) . . ?
O0AA C0BA C6BA 113.1(3) . . ?
O3AA C0BA O0AA 124.8(4) . . ?
O3AA C0BA C6BA 122.1(4) . . ?
C6AA C1BA O1 122.5(3) . . ?
C6AA C1BA C1CA 123.4(4) . . ?
C1CA C1BA O1 114.1(4) . . ?
C5BA C2BA C3BA 119.2(4) . . ?
C9AA C3BA C7BA 114.9(4) . . ?
C2BA C3BA C9AA 121.3(4) . . ?
C2BA C3BA C7BA 123.6(4) . . ?
C6BA N4BA S0AA 112.7(2) . . ?
C7BA N4BA S0AA 118.1(3) . . ?
C7BA N4BA C6BA 118.5(3) . . ?
C2BA C5BA C1 120.6(5) . . ?
C6AA C6BA C0BA 116.8(3) . . ?
C6AA C6BA C8BA 108.0(3) . . ?
C0BA C6BA C8BA 107.8(3) . . ?
N4BA C6BA C6AA 111.3(3) . . ?
N4BA C6BA C0BA 106.3(3) . . ?
N4BA C6BA C8BA 106.1(3) . . ?
N4BA C7BA C3BA 111.4(3) . . ?
C9AA C8BA C6BA 108.8(3) . . ?
O0AA C9BA C0CA 108.0(4) . . ?
C7AA C1CA C1BA 118.1(5) . . ?
C8AA C1 C5BA 120.0(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.719
_oxdiff_exptl_absorpt_empirical_full_min 0.704
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_21783
_database_code_depnum_ccdc_archive 'CCDC 2105105'
loop_
_audit_author_name
_audit_author_address
'shaonan zhang'
;shaonan zhang
China
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O5 S'
_chemical_formula_sum            'C19 H19 N O5 S'
_chemical_formula_weight         373.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 N S O'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.8137(2)
_cell_length_b                   13.8729(4)
_cell_length_c                   14.1426(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1729.24(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5814
_cell_measurement_temperature    193.15
_cell_measurement_theta_max      62.1170
_cell_measurement_theta_min      4.4460
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.594
_exptl_absorpt_coefficient_mu    1.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9479
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        62.129
_diffrn_reflns_theta_max         62.129
_diffrn_reflns_theta_min         4.465
_diffrn_ambient_temperature      193.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -20.00   1.00    7.50    --  -32.31 -38.00-180.00   81
  2  ω    -56.00  12.00   1.00    7.50    --  -32.31  90.00 -91.00   68
  3  ω   -110.00 -75.00   1.00    7.50    --  -32.31-178.00 -90.00   35
  4  ω    -63.00 -26.00   1.00    7.50    --  -32.31  77.00-150.00   37
  5  ω    -95.00 -21.00   1.00    7.50    --  -32.31 -57.00 -30.00   74
  6  ω     17.00 102.00   1.00    7.50    --   32.31  57.00 120.00   85
  7  ω     46.00  71.00   1.00    7.50    --   32.31 -99.00  90.00   25
  8  ω    -21.00  13.00   1.00    7.50    --   32.31 -99.00  90.00   34
  9  ω     69.00 102.00   1.00   27.50    --   94.50 -92.00  30.00   33
 10  ω     29.00  55.00   1.00   27.50    --   94.50 -92.00  60.00   26
 11  ω     32.00  74.00   1.00   27.50    --   94.50 -50.00  30.00   42
 12  ω     49.00  75.00   1.00   27.50    --   94.50 -92.00 -90.00   26
 13  ω     23.00 118.00   1.00   27.50    --   94.50 -50.00-120.00   95
 14  ω     78.00 104.00   1.00   27.50    --   94.50 -38.00  60.00   26
 15  ω     79.00 104.00   1.00   27.50    --   94.50 -92.00-150.00   25
 16  ω     68.00 160.00   1.00   27.50    --   94.50  64.00  30.00   92
 17  ω     21.00  67.00   1.00   27.50    --   94.50 -92.00-150.00   46
 18  ω    118.00 167.00   1.00   27.50    --   94.50  38.00   0.00   49
 19  ω     88.00 119.00   1.00   27.50    --   94.50 -50.00 120.00   31
 20  ω     24.00  70.00   1.00   27.50    --   94.50 -38.00  60.00   46
 21  ω     63.00  97.00   1.00   27.50    --   94.50  38.00   0.00   34
 22  ω     23.00  69.00   1.00   27.50    --   94.50 -50.00 120.00   46
 23  ω     24.00 153.00   1.00   27.50    --   94.50   0.00-180.00  129
 24  ω     93.00 118.00   1.00   27.50    --   94.50 -92.00  60.00   25
 25  ω     57.00 133.00   1.00   27.50    --   94.50 -93.00 -47.25   76
 26  ω     94.00 120.00   1.00   27.50    --   94.50 -92.00 -90.00   26
 27  ω     44.00 131.00   1.00   27.50    --   94.50 -93.00 131.51   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0377293000
_diffrn_orient_matrix_UB_12      0.0658238000
_diffrn_orient_matrix_UB_13      0.0846941000
_diffrn_orient_matrix_UB_21      -0.1434724000
_diffrn_orient_matrix_UB_22      -0.0356000000
_diffrn_orient_matrix_UB_23      0.0514633000
_diffrn_orient_matrix_UB_31      0.0923690000
_diffrn_orient_matrix_UB_32      -0.0820814000
_diffrn_orient_matrix_UB_33      0.0452063000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2635
_reflns_number_total             2685
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1048 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.061
_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)+(0.0717P)²+0.9471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1209
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C15(H15), C4(H4), C11(H11), C14(H14), C3(H3), C13(H13),
 C12(H12)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.79204(11) 0.36245(8) 0.17710(7) 0.0356(3) Uani 1 1 d . . . . .
O1 O 0.6664(3) 0.3252(2) 0.10391(19) 0.0374(7) Uani 1 1 d . . . . .
O5 O 0.5405(4) 0.3144(2) 0.4100(2) 0.0465(8) Uani 1 1 d . . . . .
O3 O 0.8145(4) 0.2898(2) 0.2457(2) 0.0455(8) Uani 1 1 d . . . . .
O2 O 0.9116(4) 0.3960(3) 0.1191(2) 0.0482(8) Uani 1 1 d . . . . .
O4 O 0.7123(4) 0.4315(3) 0.4266(2) 0.0481(8) Uani 1 1 d . . . . .
N1 N 0.7080(4) 0.4515(2) 0.2271(2) 0.0305(7) Uani 1 1 d . . . . .
C10 C 0.3443(5) 0.5362(3) 0.3371(3) 0.0324(9) Uani 1 1 d . . . . .
C17 C 0.6193(5) 0.3902(3) 0.3812(3) 0.0337(9) Uani 1 1 d . . . . .
C9 C 0.4990(5) 0.5287(3) 0.2930(3) 0.0315(9) Uani 1 1 d . . . . .
H9 H 0.569120 0.564740 0.335915 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5703(5) 0.4245(3) 0.2813(3) 0.0277(9) Uani 1 1 d . . . . .
C6 C 0.4719(5) 0.3530(3) 0.2269(3) 0.0284(8) Uani 1 1 d . . . . .
C1 C 0.5209(5) 0.3099(3) 0.1422(3) 0.0309(9) Uani 1 1 d . . . . .
C5 C 0.3248(5) 0.3288(3) 0.2557(3) 0.0330(9) Uani 1 1 d . . . . .
H5 H 0.287803 0.353893 0.313836 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4299(6) 0.2510(3) 0.0883(3) 0.0386(10) Uani 1 1 d . . . . .
H2 H 0.467359 0.223788 0.031286 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5221(5) 0.5714(3) 0.1951(3) 0.0372(10) Uani 1 1 d . . . . .
H8A H 0.447086 0.545432 0.149681 0.045 Uiso 1 1 calc R U . . .
H8B H 0.513574 0.642587 0.196599 0.045 Uiso 1 1 calc R U . . .
C7 C 0.6815(5) 0.5402(3) 0.1695(3) 0.0381(10) Uani 1 1 d . . . . .
H7A H 0.689421 0.525897 0.101143 0.046 Uiso 1 1 calc R U . . .
H7B H 0.755992 0.591024 0.185836 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3359(5) 0.5408(3) 0.4354(3) 0.0367(10) Uani 1 1 d . . . . .
H15 H 0.426755 0.540924 0.471580 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2319(5) 0.2700(3) 0.2027(3) 0.0396(10) Uani 1 1 d . . . . .
H4 H 0.132342 0.255593 0.224284 0.048 Uiso 1 1 calc R U . . .
C11 C 0.2109(6) 0.5388(3) 0.2858(3) 0.0438(11) Uani 1 1 d . . . . .
H11 H 0.214247 0.538632 0.218680 0.053 Uiso 1 1 calc R U . . .
C14 C 0.1979(6) 0.5450(3) 0.4810(3) 0.0472(11) Uani 1 1 d . . . . .
H14 H 0.194241 0.549141 0.547995 0.057 Uiso 1 1 calc R U . . .
C3 C 0.2833(6) 0.2316(3) 0.1178(3) 0.0421(10) Uani 1 1 d . . . . .
H3 H 0.218466 0.192502 0.080328 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0661(6) 0.5433(4) 0.4300(4) 0.0555(14) Uani 1 1 d . . . . .
H13 H -0.028949 0.543314 0.461628 0.067 Uiso 1 1 calc R U . . .
C12 C 0.0715(6) 0.5415(4) 0.3323(4) 0.0534(13) Uani 1 1 d . . . . .
H12 H -0.020005 0.542143 0.296746 0.064 Uiso 1 1 calc R U . . .
C18 C 0.5651(8) 0.2825(5) 0.5066(4) 0.0644(16) Uani 1 1 d . . . . .
H18A H 0.545731 0.212325 0.510778 0.077 Uiso 1 1 calc R U . . .
H18B H 0.672307 0.293978 0.524208 0.077 Uiso 1 1 calc R U . . .
C19 C 0.4692(9) 0.3315(6) 0.5712(5) 0.085(2) Uani 1 1 d . . . . .
H19A H 0.366766 0.336122 0.544613 0.127 Uiso 1 1 calc R U . . .
H19B H 0.509034 0.396365 0.582711 0.127 Uiso 1 1 calc R U . . .
H19C H 0.465438 0.295763 0.630960 0.127 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 1.602(3) . ?
S1 O3 1.414(3) . ?
S1 O2 1.414(3) . ?
S1 N1 1.605(3) . ?
O1 C1 1.408(5) . ?
O5 C17 1.325(5) . ?
O5 C18 1.452(6) . ?
O4 C17 1.187(5) . ?
N1 C16 1.483(5) . ?
N1 C7 1.494(5) . ?
C10 C9 1.503(6) . ?
C10 C15 1.395(6) . ?
C10 C11 1.381(6) . ?
C17 C16 1.552(5) . ?
C9 H9 1.0000 . ?
C9 C16 1.585(5) . ?
C9 C8 1.520(5) . ?
C16 C6 1.526(6) . ?
C6 C1 1.407(6) . ?
C6 C5 1.399(6) . ?
C1 C2 1.375(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.379(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.515(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C14 1.378(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.389(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(7) . ?
C14 H14 0.9500 . ?
C14 C13 1.367(8) . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.383(8) . ?
C12 H12 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.418(10) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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 N1 102.36(17) . . ?
O3 S1 O1 108.10(19) . . ?
O3 S1 O2 121.9(2) . . ?
O3 S1 N1 108.14(18) . . ?
O2 S1 O1 104.26(18) . . ?
O2 S1 N1 110.27(19) . . ?
C1 O1 S1 115.5(2) . . ?
C17 O5 C18 116.9(4) . . ?
C16 N1 S1 114.2(3) . . ?
C16 N1 C7 111.3(3) . . ?
C7 N1 S1 117.8(3) . . ?
C15 C10 C9 117.7(4) . . ?
C11 C10 C9 123.8(4) . . ?
C11 C10 C15 118.5(4) . . ?
O5 C17 C16 112.2(4) . . ?
O4 C17 O5 125.3(4) . . ?
O4 C17 C16 122.4(4) . . ?
C10 C9 H9 105.9 . . ?
C10 C9 C16 117.8(3) . . ?
C10 C9 C8 118.1(4) . . ?
C16 C9 H9 105.9 . . ?
C8 C9 H9 105.9 . . ?
C8 C9 C16 102.0(3) . . ?
N1 C16 C17 108.7(3) . . ?
N1 C16 C9 98.5(3) . . ?
N1 C16 C6 111.7(3) . . ?
C17 C16 C9 107.1(3) . . ?
C6 C16 C17 114.7(3) . . ?
C6 C16 C9 114.9(3) . . ?
C1 C6 C16 122.1(4) . . ?
C5 C6 C16 122.4(4) . . ?
C5 C6 C1 115.5(4) . . ?
C6 C1 O1 122.9(4) . . ?
C2 C1 O1 114.1(4) . . ?
C2 C1 C6 123.0(4) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 C6 122.3(4) . . ?
C4 C5 H5 118.9 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C7 C8 C9 103.3(3) . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
N1 C7 C8 104.5(3) . . ?
N1 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 119.9(5) . . ?
C12 C13 H13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(5) . . ?
C13 C12 H12 120.0 . . ?
O5 C18 H18A 109.3 . . ?
O5 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 O5 111.8(5) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 O1 C1 C6 20.8(5) . . . . ?
S1 O1 C1 C2 -160.6(3) . . . . ?
S1 N1 C16 C17 83.7(3) . . . . ?
S1 N1 C16 C9 -164.9(3) . . . . ?
S1 N1 C16 C6 -43.8(4) . . . . ?
S1 N1 C7 C8 138.1(3) . . . . ?
O1 S1 N1 C16 63.2(3) . . . . ?
O1 S1 N1 C7 -70.1(3) . . . . ?
O1 C1 C2 C3 -179.0(4) . . . . ?
O5 C17 C16 N1 -139.6(3) . . . . ?
O5 C17 C16 C9 115.0(4) . . . . ?
O5 C17 C16 C6 -13.8(5) . . . . ?
O3 S1 O1 C1 63.9(3) . . . . ?
O3 S1 N1 C16 -50.7(3) . . . . ?
O3 S1 N1 C7 175.9(3) . . . . ?
O2 S1 O1 C1 -165.0(3) . . . . ?
O2 S1 N1 C16 173.7(3) . . . . ?
O2 S1 N1 C7 40.4(4) . . . . ?
O4 C17 C16 N1 43.6(5) . . . . ?
O4 C17 C16 C9 -61.9(5) . . . . ?
O4 C17 C16 C6 169.4(4) . . . . ?
N1 S1 O1 C1 -50.1(3) . . . . ?
N1 C16 C6 C1 8.2(5) . . . . ?
N1 C16 C6 C5 -169.2(3) . . . . ?
C10 C9 C16 N1 173.9(3) . . . . ?
C10 C9 C16 C17 -73.4(4) . . . . ?
C10 C9 C16 C6 55.2(5) . . . . ?
C10 C9 C8 C7 -173.4(3) . . . . ?
C10 C15 C14 C13 1.0(7) . . . . ?
C10 C11 C12 C13 1.1(8) . . . . ?
C17 O5 C18 C19 87.4(7) . . . . ?
C17 C16 C6 C1 -116.1(4) . . . . ?
C17 C16 C6 C5 66.6(5) . . . . ?
C9 C10 C15 C14 -178.2(4) . . . . ?
C9 C10 C11 C12 177.1(4) . . . . ?
C9 C16 C6 C1 119.2(4) . . . . ?
C9 C16 C6 C5 -58.1(5) . . . . ?
C9 C8 C7 N1 24.9(4) . . . . ?
C16 N1 C7 C8 3.4(4) . . . . ?
C16 C9 C8 C7 -42.5(4) . . . . ?
C16 C6 C1 O1 3.5(6) . . . . ?
C16 C6 C1 C2 -174.9(4) . . . . ?
C16 C6 C5 C4 174.9(4) . . . . ?
C6 C1 C2 C3 -0.5(6) . . . . ?
C6 C5 C4 C3 0.5(6) . . . . ?
C1 C6 C5 C4 -2.6(6) . . . . ?
C1 C2 C3 C4 -1.7(6) . . . . ?
C5 C6 C1 O1 -179.0(3) . . . . ?
C5 C6 C1 C2 2.6(6) . . . . ?
C5 C4 C3 C2 1.7(6) . . . . ?
C8 C9 C16 N1 42.8(4) . . . . ?
C8 C9 C16 C17 155.5(3) . . . . ?
C8 C9 C16 C6 -75.9(4) . . . . ?
C7 N1 C16 C17 -139.9(3) . . . . ?
C7 N1 C16 C9 -28.6(4) . . . . ?
C7 N1 C16 C6 92.5(4) . . . . ?
C15 C10 C9 C16 86.3(5) . . . . ?
C15 C10 C9 C8 -150.4(4) . . . . ?
C15 C10 C11 C12 -2.8(7) . . . . ?
C15 C14 C13 C12 -2.8(8) . . . . ?
C11 C10 C9 C16 -93.6(5) . . . . ?
C11 C10 C9 C8 29.7(6) . . . . ?
C11 C10 C15 C14 1.8(7) . . . . ?
C14 C13 C12 C11 1.8(9) . . . . ?
C18 O5 C17 O4 3.2(7) . . . . ?
C18 O5 C17 C16 -173.5(4) . . . . ?

_olex2_date_sample_data_collection 2020-01-07
_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 2.372
_oxdiff_exptl_absorpt_empirical_full_min 0.642
