# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_11_a
_audit_block_doi                 10.5517/ccdc.csd.cc2dgy0v
_database_code_depnum_ccdc_archive 'CCDC 2218887'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2022-2w3cr 2022
loop_
_audit_author_name
_audit_author_address
'we sd'
;SHIHEZI University
China
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N O7 S'
_chemical_formula_sum            'C16 H18 N O7 S'
_chemical_formula_weight         368.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.9700(2)
_cell_length_b                   20.0713(4)
_cell_length_c                   12.4232(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.7350(10)
_cell_angle_gamma                90
_cell_volume                     1737.17(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21863
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.748
_diffrn_reflns_theta_min         2.610
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6835
_reflns_number_total             7359
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         7359
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.027
_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)+(0.0472P)²+0.6124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0956
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.51(8)
 0.49(8)
2. 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
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C23(H23), C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C15(H15A,H15B), C25(H25A,H25B), C28(H28A,H28B),
 C31(H31A,H31B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C29(H29A,H29B,H29C), C32(H32A,H32B,
 H32C)
;
_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 1.23529(12) 0.44426(4) 0.78021(6) 0.02553(19) Uani 1 1 d . . . . .
C1 C 1.1262(5) 0.45065(16) 0.9752(3) 0.0239(7) Uani 1 1 d . . . . .
N1 N 0.7721(4) 0.54975(15) 0.8336(2) 0.0256(6) Uani 1 1 d . . . . .
O1 O 1.2796(3) 0.46052(12) 0.90409(18) 0.0275(5) Uani 1 1 d . . . . .
O3 O 1.4031(4) 0.46670(14) 0.7280(2) 0.0350(6) Uani 1 1 d . . . . .
C3 C 1.0394(6) 0.42339(18) 1.1532(3) 0.0344(8) Uani 1 1 d . . . . .
H3 H 1.072973 0.410086 1.224690 0.041 Uiso 1 1 calc R U . . .
S2 S 0.18899(11) 0.57489(4) 0.45042(6) 0.02310(17) Uani 1 1 d . . . . .
C2 C 1.1795(6) 0.43073(18) 1.0789(3) 0.0294(8) Uani 1 1 d . . . . .
H2 H 1.310285 0.422357 1.097974 0.035 Uiso 1 1 calc R U . . .
N2 N 0.6688(4) 0.47785(14) 0.4011(2) 0.0248(6) Uani 1 1 d . . . . .
O2 O 1.1764(4) 0.37668(13) 0.7688(2) 0.0358(6) Uani 1 1 d . . . . .
O4 O 0.6595(4) 0.60357(13) 0.6415(2) 0.0305(6) Uani 1 1 d . . . . .
C4 C 0.8485(6) 0.4354(2) 1.1240(3) 0.0351(9) Uani 1 1 d . . . . .
H4 H 0.751495 0.430172 1.175420 0.042 Uiso 1 1 calc R U . . .
O5 O 0.8857(3) 0.68341(12) 0.64875(18) 0.0281(5) Uani 1 1 d . . . . .
C5 C 0.8002(5) 0.45485(18) 1.0203(3) 0.0308(8) Uani 1 1 d . . . . .
H5 H 0.669040 0.462488 1.001125 0.037 Uiso 1 1 calc R U . . .
C6 C 0.9386(5) 0.46363(15) 0.9429(2) 0.0218(6) Uani 1 1 d . . . . .
O6 O 1.0669(5) 0.66993(18) 0.9217(3) 0.0578(9) Uani 1 1 d . . . . .
C7 C 0.8738(5) 0.48537(16) 0.8304(2) 0.0211(6) Uani 1 1 d . . . . .
H7 H 0.785059 0.450895 0.798922 0.025 Uiso 1 1 calc R U . . .
O7 O 0.7598(4) 0.69320(14) 0.8868(2) 0.0421(7) Uani 1 1 d . . . . .
O8 O 0.1493(3) 0.56138(12) 0.32590(18) 0.0264(5) Uani 1 1 d . . . . .
C8 C 1.0386(5) 0.49724(16) 0.7525(2) 0.0215(6) Uani 1 1 d . . . . .
H8 H 0.990155 0.489515 0.676980 0.026 Uiso 1 1 calc R U . . .
O9 O 0.0213(4) 0.55043(13) 0.5008(2) 0.0315(6) Uani 1 1 d . . . . .
C9 C 1.0882(4) 0.57048(17) 0.7668(3) 0.0234(6) Uani 1 1 d . . . . .
H9A H 1.143764 0.588993 0.700730 0.028 Uiso 1 1 calc R U . . .
H9B H 1.180191 0.577151 0.828105 0.028 Uiso 1 1 calc R U . . .
O10 O 0.2441(4) 0.64236(12) 0.4664(2) 0.0319(6) Uani 1 1 d . . . . .
C10 C 0.8927(5) 0.60285(16) 0.7890(3) 0.0231(7) Uani 1 1 d . . . . .
O11 O 0.7823(4) 0.41394(13) 0.5856(2) 0.0345(6) Uani 1 1 d . . . . .
C11 C 0.7972(5) 0.62957(16) 0.6847(3) 0.0235(7) Uani 1 1 d . . . . .
O12 O 0.5467(4) 0.33823(13) 0.57254(18) 0.0294(5) Uani 1 1 d . . . . .
C12 C 0.8105(5) 0.71017(19) 0.5463(3) 0.0296(8) Uani 1 1 d . . . . .
H12A H 0.670800 0.718253 0.550322 0.036 Uiso 1 1 calc R U . . .
H12B H 0.832093 0.677961 0.487549 0.036 Uiso 1 1 calc R U . . .
O13 O 0.4237(4) 0.36366(14) 0.2799(2) 0.0367(6) Uani 1 1 d . . . . .
C13 C 0.9127(6) 0.7741(2) 0.5245(3) 0.0412(10) Uani 1 1 d . . . . .
H13A H 1.050697 0.765564 0.520416 0.062 Uiso 1 1 calc R U . . .
H13B H 0.889828 0.805725 0.582842 0.062 Uiso 1 1 calc R U . . .
H13C H 0.864407 0.792823 0.456091 0.062 Uiso 1 1 calc R U . . .
O14 O 0.7157(4) 0.33670(13) 0.34785(19) 0.0311(5) Uani 1 1 d . . . . .
C14 C 0.9194(5) 0.65924(18) 0.8729(3) 0.0299(7) Uani 1 1 d . . . . .
C17 C 0.3038(5) 0.57308(17) 0.2562(2) 0.0237(6) Uani 1 1 d . . . . .
C16 C 0.5868(8) 0.7748(3) 0.9857(4) 0.0623(14) Uani 1 1 d . . . . .
H16A H 0.548349 0.799468 0.920463 0.093 Uiso 1 1 calc R U . . .
H16B H 0.592285 0.805344 1.047292 0.093 Uiso 1 1 calc R U . . .
H16C H 0.492921 0.739584 0.998687 0.093 Uiso 1 1 calc R U . . .
C15 C 0.7742(8) 0.7453(3) 0.9719(5) 0.0633(14) Uani 1 1 d . . . . .
H15A H 0.820991 0.725231 1.040613 0.076 Uiso 1 1 calc R U . . .
H15B H 0.866657 0.780106 0.951023 0.076 Uiso 1 1 calc R U . . .
C18 C 0.2528(6) 0.59460(18) 0.1535(3) 0.0310(8) Uani 1 1 d . . . . .
H18 H 0.122139 0.602694 0.133835 0.037 Uiso 1 1 calc R U . . .
C19 C 0.3952(6) 0.60414(19) 0.0800(3) 0.0348(9) Uani 1 1 d . . . . .
H19 H 0.363326 0.618543 0.008856 0.042 Uiso 1 1 calc R U . . .
C20 C 0.5848(6) 0.59251(19) 0.1110(3) 0.0353(9) Uani 1 1 d . . . . .
H20 H 0.682792 0.598641 0.060441 0.042 Uiso 1 1 calc R U . . .
C21 C 0.6329(5) 0.57217(19) 0.2141(3) 0.0293(7) Uani 1 1 d . . . . .
H21 H 0.764092 0.565300 0.234093 0.035 Uiso 1 1 calc R U . . .
C22 C 0.4919(5) 0.56145(15) 0.2902(3) 0.0217(6) Uani 1 1 d . . . . .
C23 C 0.5545(5) 0.53978(16) 0.4029(2) 0.0205(6) Uani 1 1 d . . . . .
H23 H 0.634262 0.575909 0.437042 0.025 Uiso 1 1 calc R U . . .
C24 C 0.3873(4) 0.52297(16) 0.4774(2) 0.0201(6) Uani 1 1 d . . . . .
H24 H 0.431419 0.528934 0.554185 0.024 Uiso 1 1 calc R U . . .
C25 C 0.3482(5) 0.44904(16) 0.4561(3) 0.0227(6) Uani 1 1 d . . . . .
H25A H 0.263001 0.442714 0.391736 0.027 Uiso 1 1 calc R U . . .
H25B H 0.289729 0.427462 0.518861 0.027 Uiso 1 1 calc R U . . .
C26 C 0.5514(5) 0.42156(16) 0.4375(3) 0.0224(7) Uani 1 1 d . . . . .
C27 C 0.6422(5) 0.39149(17) 0.5410(3) 0.0249(7) Uani 1 1 d . . . . .
C28 C 0.6204(6) 0.30635(19) 0.6713(3) 0.0354(9) Uani 1 1 d . . . . .
H28A H 0.621049 0.338612 0.731561 0.043 Uiso 1 1 calc R U . . .
H28B H 0.753621 0.290871 0.661539 0.043 Uiso 1 1 calc R U . . .
C29 C 0.4951(7) 0.24894(19) 0.6959(3) 0.0392(9) Uani 1 1 d . . . . .
H29A H 0.494129 0.217491 0.635513 0.059 Uiso 1 1 calc R U . . .
H29B H 0.364285 0.264793 0.707143 0.059 Uiso 1 1 calc R U . . .
H29C H 0.544217 0.226591 0.761219 0.059 Uiso 1 1 calc R U . . .
C30 C 0.5500(5) 0.36982(17) 0.3467(3) 0.0257(7) Uani 1 1 d . . . . .
C31 C 0.7420(6) 0.28792(19) 0.2623(3) 0.0335(8) Uani 1 1 d . . . . .
H31A H 0.880066 0.276987 0.257928 0.040 Uiso 1 1 calc R U . . .
H31B H 0.698714 0.307304 0.192474 0.040 Uiso 1 1 calc R U . . .
C32 C 0.6315(6) 0.2259(2) 0.2828(3) 0.0379(9) Uani 1 1 d . . . . .
H32A H 0.493897 0.236008 0.280544 0.057 Uiso 1 1 calc R U . . .
H32B H 0.668736 0.208208 0.353964 0.057 Uiso 1 1 calc R U . . .
H32C H 0.659263 0.192779 0.227531 0.057 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 1.594(2) . ?
S1 O3 1.427(3) . ?
S1 O2 1.423(3) . ?
S1 C8 1.761(3) . ?
C1 O1 1.422(4) . ?
C1 C2 1.388(5) . ?
C1 C6 1.381(5) . ?
N1 C7 1.475(4) . ?
N1 C10 1.476(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.372(5) . ?
C3 C4 1.390(6) . ?
S2 O8 1.587(2) . ?
S2 O9 1.429(3) . ?
S2 O10 1.420(3) . ?
S2 C24 1.755(3) . ?
C2 H2 0.9500 . ?
N2 C23 1.477(4) . ?
N2 C26 1.474(4) . ?
O4 C11 1.205(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(5) . ?
O5 C11 1.328(4) . ?
O5 C12 1.464(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(5) . ?
C6 C7 1.519(4) . ?
O6 C14 1.197(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.543(4) . ?
O7 C14 1.321(5) . ?
O7 C15 1.489(5) . ?
O8 C17 1.422(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.519(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.542(4) . ?
C10 C11 1.535(4) . ?
C10 C14 1.546(5) . ?
O11 C27 1.196(4) . ?
O12 C27 1.325(4) . ?
O12 C28 1.463(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.496(5) . ?
O13 C30 1.198(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O14 C30 1.332(4) . ?
O14 C31 1.460(4) . ?
C17 C18 1.383(4) . ?
C17 C22 1.385(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C15 1.449(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C19 1.382(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.400(4) . ?
C22 C23 1.519(4) . ?
C23 H23 1.0000 . ?
C23 C24 1.547(4) . ?
C24 H24 1.0000 . ?
C24 C25 1.530(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.544(4) . ?
C26 C27 1.539(4) . ?
C26 C30 1.533(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.483(6) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.489(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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 C8 101.05(14) . . ?
O3 S1 O1 103.67(15) . . ?
O3 S1 C8 111.39(16) . . ?
O2 S1 O1 109.76(15) . . ?
O2 S1 O3 119.57(17) . . ?
O2 S1 C8 109.62(16) . . ?
C2 C1 O1 115.6(3) . . ?
C6 C1 O1 121.1(3) . . ?
C6 C1 C2 123.3(3) . . ?
C7 N1 C10 110.1(3) . . ?
C1 O1 S1 116.4(2) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
O8 S2 C24 101.43(14) . . ?
O9 S2 O8 104.32(14) . . ?
O9 S2 C24 111.23(15) . . ?
O10 S2 O8 109.75(14) . . ?
O10 S2 O9 119.18(16) . . ?
O10 S2 C24 109.35(16) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C26 N2 C23 109.6(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C11 O5 C12 115.7(3) . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 116.4(3) . . ?
C1 C6 C7 125.0(3) . . ?
C5 C6 C7 118.6(3) . . ?
N1 C7 C6 110.9(3) . . ?
N1 C7 H7 108.9 . . ?
N1 C7 C8 104.4(3) . . ?
C6 C7 H7 108.9 . . ?
C6 C7 C8 114.5(3) . . ?
C8 C7 H7 108.9 . . ?
C14 O7 C15 114.6(3) . . ?
C17 O8 S2 116.9(2) . . ?
S1 C8 H8 109.2 . . ?
C7 C8 S1 112.0(2) . . ?
C7 C8 H8 109.2 . . ?
C9 C8 S1 112.9(2) . . ?
C9 C8 C7 104.3(3) . . ?
C9 C8 H8 109.2 . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C8 C9 C10 103.2(3) . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
N1 C10 C9 106.2(3) . . ?
N1 C10 C11 109.4(3) . . ?
N1 C10 C14 109.5(3) . . ?
C9 C10 C14 109.9(3) . . ?
C11 C10 C9 111.0(3) . . ?
C11 C10 C14 110.7(3) . . ?
O4 C11 O5 125.0(3) . . ?
O4 C11 C10 123.0(3) . . ?
O5 C11 C10 112.0(3) . . ?
C27 O12 C28 115.7(3) . . ?
O5 C12 H12A 110.1 . . ?
O5 C12 H12B 110.1 . . ?
O5 C12 C13 108.2(3) . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
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 . . ?
C30 O14 C31 117.0(3) . . ?
O6 C14 O7 123.7(4) . . ?
O6 C14 C10 123.8(3) . . ?
O7 C14 C10 112.4(3) . . ?
C18 C17 O8 115.8(3) . . ?
C18 C17 C22 123.3(3) . . ?
C22 C17 O8 120.9(3) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
O7 C15 H15A 109.8 . . ?
O7 C15 H15B 109.8 . . ?
C16 C15 O7 109.2(4) . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.1(3) . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 116.5(3) . . ?
C17 C22 C23 124.9(3) . . ?
C21 C22 C23 118.6(3) . . ?
N2 C23 C22 111.5(3) . . ?
N2 C23 H23 108.9 . . ?
N2 C23 C24 104.0(2) . . ?
C22 C23 H23 108.9 . . ?
C22 C23 C24 114.4(3) . . ?
C24 C23 H23 108.9 . . ?
S2 C24 H24 109.2 . . ?
C23 C24 S2 111.1(2) . . ?
C23 C24 H24 109.2 . . ?
C25 C24 S2 114.0(2) . . ?
C25 C24 C23 104.0(2) . . ?
C25 C24 H24 109.2 . . ?
C24 C25 H25A 111.3 . . ?
C24 C25 H25B 111.3 . . ?
C24 C25 C26 102.3(3) . . ?
H25A C25 H25B 109.2 . . ?
C26 C25 H25A 111.3 . . ?
C26 C25 H25B 111.3 . . ?
N2 C26 C25 107.0(3) . . ?
N2 C26 C27 109.8(3) . . ?
N2 C26 C30 106.5(3) . . ?
C27 C26 C25 111.8(3) . . ?
C30 C26 C25 111.6(3) . . ?
C30 C26 C27 110.0(3) . . ?
O11 C27 O12 125.3(3) . . ?
O11 C27 C26 123.3(3) . . ?
O12 C27 C26 111.5(3) . . ?
O12 C28 H28A 110.0 . . ?
O12 C28 H28B 110.0 . . ?
O12 C28 C29 108.6(3) . . ?
H28A C28 H28B 108.4 . . ?
C29 C28 H28A 110.0 . . ?
C29 C28 H28B 110.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O13 C30 O14 125.1(3) . . ?
O13 C30 C26 124.6(3) . . ?
O14 C30 C26 110.1(3) . . ?
O14 C31 H31A 109.4 . . ?
O14 C31 H31B 109.4 . . ?
O14 C31 C32 111.0(3) . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C8 C9 C10 -155.7(2) . . . . ?
C1 C6 C7 N1 -121.9(3) . . . . ?
C1 C6 C7 C8 -4.1(5) . . . . ?
N1 C7 C8 S1 153.4(2) . . . . ?
N1 C7 C8 C9 31.0(3) . . . . ?
N1 C10 C11 O4 -9.2(4) . . . . ?
N1 C10 C11 O5 171.5(3) . . . . ?
N1 C10 C14 O6 108.1(4) . . . . ?
N1 C10 C14 O7 -70.2(4) . . . . ?
O1 S1 C8 C7 -55.2(2) . . . . ?
O1 S1 C8 C9 62.2(2) . . . . ?
O1 C1 C2 C3 176.9(3) . . . . ?
O1 C1 C6 C5 -177.5(3) . . . . ?
O1 C1 C6 C7 3.5(5) . . . . ?
O3 S1 O1 C1 172.7(2) . . . . ?
O3 S1 C8 C7 -164.8(2) . . . . ?
O3 S1 C8 C9 -47.4(3) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
S2 O8 C17 C18 -148.1(3) . . . . ?
S2 O8 C17 C22 33.6(4) . . . . ?
S2 C24 C25 C26 156.3(2) . . . . ?
C2 C1 O1 S1 147.7(3) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C2 C1 C6 C7 -179.9(3) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
N2 C23 C24 S2 -156.7(2) . . . . ?
N2 C23 C24 C25 -33.6(3) . . . . ?
N2 C26 C27 O11 3.3(5) . . . . ?
N2 C26 C27 O12 -176.3(3) . . . . ?
N2 C26 C30 O13 -97.9(4) . . . . ?
N2 C26 C30 O14 77.1(3) . . . . ?
O2 S1 O1 C1 -58.4(3) . . . . ?
O2 S1 C8 C7 60.6(3) . . . . ?
O2 S1 C8 C9 178.0(2) . . . . ?
C4 C3 C2 C1 0.4(6) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C4 C5 C6 C7 -179.8(3) . . . . ?
C5 C6 C7 N1 59.1(4) . . . . ?
C5 C6 C7 C8 176.9(3) . . . . ?
C6 C1 O1 S1 -35.4(4) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C6 C7 C8 S1 31.9(3) . . . . ?
C6 C7 C8 C9 -90.5(3) . . . . ?
C7 N1 C10 C9 -5.5(3) . . . . ?
C7 N1 C10 C11 114.4(3) . . . . ?
C7 N1 C10 C14 -124.1(3) . . . . ?
C7 C8 C9 C10 -33.9(3) . . . . ?
O8 S2 C24 C23 56.5(2) . . . . ?
O8 S2 C24 C25 -60.6(2) . . . . ?
O8 C17 C18 C19 -177.2(3) . . . . ?
O8 C17 C22 C21 177.7(3) . . . . ?
O8 C17 C22 C23 -3.7(5) . . . . ?
C8 S1 O1 C1 57.3(3) . . . . ?
C8 C9 C10 N1 24.6(3) . . . . ?
C8 C9 C10 C11 -94.2(3) . . . . ?
C8 C9 C10 C14 143.0(3) . . . . ?
O9 S2 O8 C17 -172.2(2) . . . . ?
O9 S2 C24 C23 166.9(2) . . . . ?
O9 S2 C24 C25 49.9(3) . . . . ?
C9 C10 C11 O4 107.7(4) . . . . ?
C9 C10 C11 O5 -71.6(3) . . . . ?
C9 C10 C14 O6 -8.2(5) . . . . ?
C9 C10 C14 O7 173.5(3) . . . . ?
O10 S2 O8 C17 59.0(3) . . . . ?
O10 S2 C24 C23 -59.4(3) . . . . ?
O10 S2 C24 C25 -176.4(2) . . . . ?
C10 N1 C7 C6 108.1(3) . . . . ?
C10 N1 C7 C8 -15.7(3) . . . . ?
C11 O5 C12 C13 174.1(3) . . . . ?
C11 C10 C14 O6 -131.2(4) . . . . ?
C11 C10 C14 O7 50.5(4) . . . . ?
C12 O5 C11 O4 -2.5(5) . . . . ?
C12 O5 C11 C10 176.8(3) . . . . ?
C14 O7 C15 C16 -175.1(4) . . . . ?
C14 C10 C11 O4 -130.0(4) . . . . ?
C14 C10 C11 O5 50.8(4) . . . . ?
C17 C18 C19 C20 -0.5(6) . . . . ?
C17 C22 C23 N2 124.6(3) . . . . ?
C17 C22 C23 C24 6.9(4) . . . . ?
C15 O7 C14 O6 -2.1(6) . . . . ?
C15 O7 C14 C10 176.2(4) . . . . ?
C18 C17 C22 C21 -0.4(5) . . . . ?
C18 C17 C22 C23 178.1(3) . . . . ?
C18 C19 C20 C21 -0.6(6) . . . . ?
C19 C20 C21 C22 1.2(6) . . . . ?
C20 C21 C22 C17 -0.7(5) . . . . ?
C20 C21 C22 C23 -179.3(3) . . . . ?
C21 C22 C23 N2 -56.9(4) . . . . ?
C21 C22 C23 C24 -174.6(3) . . . . ?
C22 C17 C18 C19 1.1(5) . . . . ?
C22 C23 C24 S2 -34.8(3) . . . . ?
C22 C23 C24 C25 88.3(3) . . . . ?
C23 N2 C26 C25 3.8(3) . . . . ?
C23 N2 C26 C27 -117.7(3) . . . . ?
C23 N2 C26 C30 123.2(3) . . . . ?
C23 C24 C25 C26 35.2(3) . . . . ?
C24 S2 O8 C17 -56.5(3) . . . . ?
C24 C25 C26 N2 -24.5(3) . . . . ?
C24 C25 C26 C27 95.7(3) . . . . ?
C24 C25 C26 C30 -140.7(3) . . . . ?
C25 C26 C27 O11 -115.3(4) . . . . ?
C25 C26 C27 O12 65.1(4) . . . . ?
C25 C26 C30 O13 18.6(5) . . . . ?
C25 C26 C30 O14 -166.5(3) . . . . ?
C26 N2 C23 C22 -105.4(3) . . . . ?
C26 N2 C23 C24 18.4(3) . . . . ?
C27 O12 C28 C29 178.8(3) . . . . ?
C27 C26 C30 O13 143.2(3) . . . . ?
C27 C26 C30 O14 -41.9(4) . . . . ?
C28 O12 C27 O11 1.2(5) . . . . ?
C28 O12 C27 C26 -179.3(3) . . . . ?
C30 O14 C31 C32 -76.3(4) . . . . ?
C30 C26 C27 O11 120.2(4) . . . . ?
C30 C26 C27 O12 -59.3(4) . . . . ?
C31 O14 C30 O13 -1.7(5) . . . . ?
C31 O14 C30 C26 -176.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.51(8)
2 0.49(8)

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2347754'
loop_
_audit_author_name
_audit_author_address
'we sd'
;SHIHEZI University
China
;
_audit_update_record             
;
2024-04-12 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_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_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.3087(3)
_cell_length_b                   18.9005(5)
_cell_length_c                   16.1113(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.4740(10)
_cell_angle_gamma                90
_cell_volume                     3659.66(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9086
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      26.62
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0781 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8968.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22145
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.737
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3181
_reflns_number_total             3884
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.049
_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)+(0.0577P)²+2.7712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1279
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
4.d Fitted hexagon refined as free rotating group:
 C12(C13,C14,C15,C16,C11)
4.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.52397(4) 0.24596(3) 0.53154(3) 0.04645(16) Uani 1 1 d . . . . .
O1 O 0.39736(12) 0.24121(8) 0.48217(9) 0.0572(4) Uani 1 1 d . . . . .
O2 O 0.58835(14) 0.19938(8) 0.49272(14) 0.0800(5) Uani 1 1 d . . . . .
O3 O 0.51808(13) 0.23583(9) 0.61735(10) 0.0689(5) Uani 1 1 d . . . . .
O4 O 0.80607(11) 0.50029(7) 0.52934(9) 0.0532(4) Uani 1 1 d . . . . .
O5 O 0.62873(12) 0.53569(8) 0.49712(10) 0.0623(4) Uani 1 1 d . . . . .
N1 N 0.57078(14) 0.41376(9) 0.40151(10) 0.0483(4) Uani 1 1 d D . . . .
C1 C 0.35685(15) 0.27233(11) 0.40176(11) 0.0460(4) Uani 1 1 d . . . . .
C2 C 0.25108(18) 0.25089(13) 0.36308(13) 0.0573(5) Uani 1 1 d . . . . .
H2 H 0.214213 0.216853 0.388327 0.069 Uiso 1 1 calc R U . . .
C3 C 0.20097(19) 0.28063(16) 0.28660(14) 0.0692(7) Uani 1 1 d . . . . .
H3 H 0.129480 0.266901 0.259670 0.083 Uiso 1 1 calc R U . . .
C4 C 0.2567(2) 0.33075(16) 0.24989(14) 0.0715(7) Uani 1 1 d . . . . .
H4 H 0.222743 0.350369 0.197800 0.086 Uiso 1 1 calc R U . . .
C5 C 0.36226(18) 0.35224(14) 0.28944(12) 0.0588(6) Uani 1 1 d . . . . .
H5 H 0.398412 0.386486 0.263919 0.071 Uiso 1 1 calc R U . . .
C6 C 0.41550(15) 0.32325(11) 0.36724(11) 0.0445(4) Uani 1 1 d . . . . .
C7 C 0.53170(15) 0.34175(10) 0.41128(11) 0.0419(4) Uani 1 1 d . . . . .
H7 H 0.582076 0.309069 0.390997 0.050 Uiso 1 1 calc R U . . .
C8 C 0.55148(14) 0.33370(9) 0.50810(10) 0.0371(4) Uani 1 1 d . . . . .
H8 H 0.500283 0.364981 0.529577 0.044 Uiso 1 1 calc R U . . .
C9 C 0.67048(14) 0.36089(9) 0.53890(11) 0.0385(4) Uani 1 1 d . . . . .
H9 H 0.720964 0.321947 0.533283 0.046 Uiso 1 1 calc R U . . .
C10 C 0.67602(15) 0.41703(10) 0.46527(11) 0.0423(4) Uani 1 1 d . . . . .
H10 H 0.736259 0.402833 0.437745 0.051 Uiso 1 1 calc R U . . .
C12 C 0.62869(9) 0.42552(8) 0.66731(8) 0.0585(5) Uani 1 1 d G . . . .
H12 H 0.557069 0.434894 0.636602 0.070 Uiso 1 1 calc R U . . .
C13 C 0.66238(12) 0.44992(9) 0.75028(8) 0.0717(7) Uani 1 1 d G . . . .
H13 H 0.613308 0.475627 0.775081 0.086 Uiso 1 1 calc R U . . .
C14 C 0.76943(13) 0.43590(10) 0.79618(7) 0.0735(7) Uani 1 1 d G . . . .
H14 H 0.791971 0.452233 0.851686 0.088 Uiso 1 1 calc R U . . .
C15 C 0.84278(10) 0.39748(10) 0.75910(8) 0.0763(7) Uani 1 1 d G . . . .
H15 H 0.914397 0.388108 0.789813 0.092 Uiso 1 1 calc R U . . .
C16 C 0.80908(9) 0.37308(8) 0.67614(8) 0.0588(5) Uani 1 1 d G . . . .
H16 H 0.858160 0.347374 0.651335 0.071 Uiso 1 1 calc R U . . .
C11 C 0.70204(10) 0.38710(7) 0.63024(6) 0.0419(4) Uani 1 1 d G . . . .
C17 C 0.69900(15) 0.49146(10) 0.49805(11) 0.0437(4) Uani 1 1 d . . . . .
C18 C 0.8408(2) 0.56615(13) 0.57401(18) 0.0728(7) Uani 1 1 d . . . . .
H18A H 0.794527 0.576100 0.614301 0.087 Uiso 1 1 calc R U . . .
H18B H 0.833697 0.605054 0.533941 0.087 Uiso 1 1 calc R U . . .
C19 C 0.9575(3) 0.55797(17) 0.6188(3) 0.1144(13) Uani 1 1 d . U . . .
H19A H 1.002502 0.548251 0.578360 0.172 Uiso 1 1 calc R U . . .
H19B H 0.963492 0.519493 0.658426 0.172 Uiso 1 1 calc R U . . .
H19C H 0.982593 0.600823 0.648856 0.172 Uiso 1 1 calc R U . . .
H1 H 0.524(2) 0.4439(16) 0.415(2) 0.137 Uiso 1 1 d D 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 1.5918(15) . ?
S1 O2 1.4170(17) . ?
S1 O3 1.4129(16) . ?
S1 C8 1.7501(18) . ?
O1 C1 1.412(2) . ?
O4 C17 1.316(2) . ?
O4 C18 1.455(3) . ?
O5 C17 1.201(2) . ?
N1 C7 1.463(2) . ?
N1 C10 1.471(2) . ?
N1 H1 0.874(10) . ?
C1 C2 1.377(3) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C6 C7 1.494(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.533(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.530(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.604(2) . ?
C9 C11 1.5214(18) . ?
C10 H10 0.9800 . ?
C10 C17 1.508(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C12 C11 1.3900 . ?
C13 H13 0.9300 . ?
C13 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C11 1.3900 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.469(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C8 99.19(8) . . ?
O2 S1 O1 108.96(10) . . ?
O2 S1 C8 109.92(9) . . ?
O3 S1 O1 103.28(9) . . ?
O3 S1 O2 119.96(12) . . ?
O3 S1 C8 113.12(9) . . ?
C1 O1 S1 123.27(12) . . ?
C17 O4 C18 117.45(17) . . ?
C7 N1 C10 102.96(14) . . ?
C7 N1 H1 109(3) . . ?
C10 N1 H1 109(2) . . ?
C2 C1 O1 113.87(18) . . ?
C2 C1 C6 123.01(18) . . ?
C6 C1 O1 123.00(16) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 116.61(18) . . ?
C1 C6 C7 119.92(16) . . ?
C5 C6 C7 123.40(18) . . ?
N1 C7 C6 118.01(16) . . ?
N1 C7 H7 107.7 . . ?
N1 C7 C8 102.59(14) . . ?
C6 C7 H7 107.7 . . ?
C6 C7 C8 112.66(14) . . ?
C8 C7 H7 107.7 . . ?
S1 C8 H8 109.0 . . ?
C7 C8 S1 108.53(12) . . ?
C7 C8 H8 109.0 . . ?
C9 C8 S1 117.68(12) . . ?
C9 C8 C7 103.13(13) . . ?
C9 C8 H8 109.0 . . ?
C8 C9 H9 107.4 . . ?
C8 C9 C10 99.96(13) . . ?
C10 C9 H9 107.4 . . ?
C11 C9 C8 116.71(13) . . ?
C11 C9 H9 107.4 . . ?
C11 C9 C10 117.21(14) . . ?
N1 C10 C9 108.50(13) . . ?
N1 C10 H10 108.1 . . ?
N1 C10 C17 110.74(15) . . ?
C9 C10 H10 108.1 . . ?
C17 C10 C9 113.13(14) . . ?
C17 C10 H10 108.1 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C11 120.0 . . ?
C11 C16 H16 120.0 . . ?
C12 C11 C9 122.13(10) . . ?
C16 C11 C9 117.85(10) . . ?
C16 C11 C12 120.0 . . ?
O4 C17 C10 110.43(16) . . ?
O5 C17 O4 125.14(18) . . ?
O5 C17 C10 124.41(17) . . ?
O4 C18 H18A 110.2 . . ?
O4 C18 H18B 110.2 . . ?
O4 C18 C19 107.7(2) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
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 C2 168.19(15) . . . . ?
S1 O1 C1 C6 -15.7(3) . . . . ?
S1 C8 C9 C10 148.94(12) . . . . ?
S1 C8 C9 C11 -83.61(16) . . . . ?
O1 S1 C8 C7 -59.38(13) . . . . ?
O1 S1 C8 C9 -175.89(13) . . . . ?
O1 C1 C2 C3 176.6(2) . . . . ?
O1 C1 C6 C5 -176.36(18) . . . . ?
O1 C1 C6 C7 6.6(3) . . . . ?
O2 S1 O1 C1 -75.05(18) . . . . ?
O2 S1 C8 C7 54.74(15) . . . . ?
O2 S1 C8 C9 -61.76(16) . . . . ?
O3 S1 O1 C1 156.37(16) . . . . ?
O3 S1 C8 C7 -168.17(12) . . . . ?
O3 S1 C8 C9 75.32(15) . . . . ?
N1 C7 C8 S1 -173.14(12) . . . . ?
N1 C7 C8 C9 -47.61(17) . . . . ?
N1 C10 C17 O4 -157.14(14) . . . . ?
N1 C10 C17 O5 24.3(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 C6 C7 N1 -150.27(18) . . . . ?
C1 C6 C7 C8 -30.9(2) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C6 C7 -177.62(18) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 177.0(2) . . . . ?
C5 C6 C7 N1 32.9(3) . . . . ?
C5 C6 C7 C8 152.20(19) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C7 C8 S1 58.93(18) . . . . ?
C6 C7 C8 C9 -175.54(15) . . . . ?
C7 N1 C10 C9 -25.60(17) . . . . ?
C7 N1 C10 C17 -150.33(14) . . . . ?
C7 C8 C9 C10 29.55(16) . . . . ?
C7 C8 C9 C11 157.00(14) . . . . ?
C8 S1 O1 C1 39.83(17) . . . . ?
C8 C9 C10 N1 -3.29(17) . . . . ?
C8 C9 C10 C17 120.01(15) . . . . ?
C8 C9 C11 C12 -38.83(19) . . . . ?
C8 C9 C11 C16 142.84(13) . . . . ?
C9 C10 C17 O4 80.81(18) . . . . ?
C9 C10 C17 O5 -97.7(2) . . . . ?
C10 N1 C7 C6 169.02(15) . . . . ?
C10 N1 C7 C8 44.55(16) . . . . ?
C10 C9 C11 C12 79.62(16) . . . . ?
C10 C9 C11 C16 -98.71(15) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C12 C11 C9 -178.30(14) . . . . ?
C13 C12 C11 C16 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C15 C16 C11 C9 178.37(14) . . . . ?
C15 C16 C11 C12 0.0 . . . . ?
C11 C9 C10 N1 -130.40(14) . . . . ?
C11 C9 C10 C17 -7.1(2) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C17 O4 C18 C19 167.7(2) . . . . ?
C18 O4 C17 O5 6.6(3) . . . . ?
C18 O4 C17 C10 -171.91(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2353272'
loop_
_audit_author_name
_audit_author_address
'we sd'
;SHIHEZI University
China
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2024-05-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O6 S'
_chemical_formula_sum            'C23 H20 N2 O6 S'
_chemical_formula_weight         452.47
_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      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                   7.3391(6)
_cell_length_b                   27.293(2)
_cell_length_c                   10.5772(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.174(3)
_cell_angle_gamma                90
_cell_volume                     2044.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8097
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      71.52
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.714
_shelx_estimated_absorpt_T_min   0.692
_exptl_absorpt_coefficient_mu    1.804
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1334 before and 0.0575 after correction.
The Ratio of minimum to maximum transmission is 0.8840.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15630
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.984
_diffrn_reflns_theta_min         4.624
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3353
_reflns_number_total             3926
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3926
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.044
_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)+(0.0426P)²+1.3437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.11172(7) 0.75782(2) 0.24602(5) 0.02860(14) Uani 1 1 d . . . . .
O1 O 0.1786(3) 0.81321(6) 0.2717(2) 0.0647(6) Uani 1 1 d . . . . .
O2 O 0.1031(3) 0.74976(7) 0.11250(15) 0.0516(4) Uani 1 1 d . . . . .
O3 O -0.0561(2) 0.75210(6) 0.28574(17) 0.0483(4) Uani 1 1 d . . . . .
O4 O -0.1612(2) 0.52105(6) 0.37338(16) 0.0418(4) Uani 1 1 d . . . . .
O5 O 0.8854(3) 0.55674(7) 0.92881(16) 0.0560(5) Uani 1 1 d . . . . .
O6 O 0.6565(3) 0.50661(7) 0.84494(19) 0.0550(5) Uani 1 1 d . . . . .
N1 N 0.6247(2) 0.71482(6) 0.4117(2) 0.0387(4) Uani 1 1 d D . . . .
N2 N 0.7467(3) 0.54390(7) 0.84113(18) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.3343(3) 0.82903(8) 0.3731(2) 0.0353(5) Uani 1 1 d . . . . .
C2 C 0.3229(4) 0.87509(8) 0.4236(2) 0.0428(5) Uani 1 1 d . . . . .
H2 H 0.211730 0.894287 0.394935 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4784(4) 0.89266(9) 0.5174(2) 0.0466(6) Uani 1 1 d . . . . .
H3 H 0.475735 0.924645 0.552301 0.056 Uiso 1 1 calc R U . . .
H1 H 0.734(2) 0.7187(10) 0.396(3) 0.056 Uiso 1 1 d D U . . .
C4 C 0.6374(4) 0.86373(9) 0.5604(2) 0.0451(6) Uani 1 1 d . . . . .
H4 H 0.742533 0.875811 0.625753 0.054 Uiso 1 1 calc R U . . .
C5 C 0.6447(3) 0.81734(8) 0.5090(2) 0.0379(5) Uani 1 1 d . . . . .
H5 H 0.753895 0.797604 0.540154 0.045 Uiso 1 1 calc R U . . .
C6 C 0.4935(3) 0.79961(7) 0.41240(19) 0.0298(4) Uani 1 1 d . . . . .
C7 C 0.4857(3) 0.75074(7) 0.3467(2) 0.0296(4) Uani 1 1 d . . . . .
H7 H 0.491791 0.755201 0.254093 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3013(3) 0.72527(7) 0.34933(18) 0.0257(4) Uani 1 1 d . . . . .
H8 H 0.287156 0.724992 0.440819 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3326(3) 0.67322(7) 0.30720(19) 0.0274(4) Uani 1 1 d . . . . .
H9 H 0.326741 0.674594 0.211738 0.033 Uiso 1 1 calc R U . . .
C10 C 0.5464(3) 0.66511(7) 0.3827(2) 0.0299(4) Uani 1 1 d . . . . .
H10 H 0.610825 0.649323 0.320801 0.036 Uiso 1 1 calc R U . . .
C11 C 0.1937(3) 0.63461(7) 0.32354(18) 0.0258(4) Uani 1 1 d . . . . .
C12 C 0.1193(3) 0.63206(7) 0.4320(2) 0.0309(4) Uani 1 1 d . . . . .
H12 H 0.149870 0.656844 0.497197 0.037 Uiso 1 1 calc R U . . .
C13 C 0.0020(3) 0.59403(8) 0.4460(2) 0.0336(4) Uani 1 1 d . . . . .
H13 H -0.047211 0.592878 0.520579 0.040 Uiso 1 1 calc R U . . .
C14 C -0.0446(3) 0.55740(7) 0.3516(2) 0.0302(4) Uani 1 1 d . . . . .
C15 C 0.0256(3) 0.55948(7) 0.24248(19) 0.0296(4) Uani 1 1 d . . . . .
H15 H -0.006249 0.534826 0.176986 0.036 Uiso 1 1 calc R U . . .
C16 C 0.1432(3) 0.59801(7) 0.22965(19) 0.0294(4) Uani 1 1 d . . . . .
H16 H 0.190493 0.599371 0.154283 0.035 Uiso 1 1 calc R U . . .
C17 C -0.1942(3) 0.48130(8) 0.2835(3) 0.0461(6) Uani 1 1 d . . . . .
H17A H -0.262667 0.493081 0.196532 0.069 Uiso 1 1 calc R U . . .
H17B H -0.269563 0.456215 0.312843 0.069 Uiso 1 1 calc R U . . .
H17C H -0.073216 0.467182 0.279208 0.069 Uiso 1 1 calc R U . . .
C18 C 0.5864(3) 0.63417(7) 0.50656(19) 0.0264(4) Uani 1 1 d . . . . .
C19 C 0.6752(3) 0.65399(7) 0.6277(2) 0.0308(4) Uani 1 1 d . . . . .
H19 H 0.698331 0.688249 0.635291 0.037 Uiso 1 1 calc R U . . .
C20 C 0.7309(3) 0.62461(8) 0.7378(2) 0.0335(4) Uani 1 1 d . . . . .
H20 H 0.796589 0.638087 0.819898 0.040 Uiso 1 1 calc R U . . .
C21 C 0.6887(3) 0.57535(7) 0.72551(19) 0.0302(4) Uani 1 1 d . . . . .
C22 C 0.5976(3) 0.55438(7) 0.6069(2) 0.0323(4) Uani 1 1 d . . . . .
H22 H 0.568592 0.520392 0.600858 0.039 Uiso 1 1 calc R U . . .
C23 C 0.5498(3) 0.58395(7) 0.4975(2) 0.0303(4) Uani 1 1 d . . . . .
H23 H 0.491032 0.569915 0.414655 0.036 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 1.5905(17) . ?
S1 O2 1.4142(17) . ?
S1 O3 1.4103(16) . ?
S1 C8 1.7674(19) . ?
O1 C1 1.415(3) . ?
O4 C14 1.369(2) . ?
O4 C17 1.421(3) . ?
O5 N2 1.235(3) . ?
O6 N2 1.220(3) . ?
N1 H1 0.868(10) . ?
N1 C7 1.451(3) . ?
N1 C10 1.474(3) . ?
N2 C21 1.463(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C6 C7 1.498(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.528(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.524(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.579(3) . ?
C9 C11 1.507(3) . ?
C10 H10 1.0000 . ?
C10 C18 1.521(3) . ?
C11 C12 1.395(3) . ?
C11 C16 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(3) . ?
C14 C15 1.382(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.387(3) . ?
C18 C23 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(3) . ?
C21 C22 1.382(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(3) . ?
C23 H23 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 C8 102.38(9) . . ?
O2 S1 O1 104.44(12) . . ?
O2 S1 C8 111.19(10) . . ?
O3 S1 O1 108.01(12) . . ?
O3 S1 O2 117.77(11) . . ?
O3 S1 C8 111.58(9) . . ?
C1 O1 S1 124.85(14) . . ?
C14 O4 C17 116.46(17) . . ?
C7 N1 H1 113.4(19) . . ?
C7 N1 C10 109.63(16) . . ?
C10 N1 H1 113.6(19) . . ?
O5 N2 C21 117.6(2) . . ?
O6 N2 O5 124.0(2) . . ?
O6 N2 C21 118.37(19) . . ?
C2 C1 O1 117.0(2) . . ?
C2 C1 C6 122.9(2) . . ?
C6 C1 O1 119.99(19) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.1(2) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 116.67(18) . . ?
C5 C6 C1 117.9(2) . . ?
C5 C6 C7 125.42(19) . . ?
N1 C7 C6 116.44(18) . . ?
N1 C7 H7 109.9 . . ?
N1 C7 C8 101.55(15) . . ?
C6 C7 H7 109.9 . . ?
C6 C7 C8 108.87(16) . . ?
C8 C7 H7 109.9 . . ?
S1 C8 H8 109.7 . . ?
C7 C8 S1 108.53(13) . . ?
C7 C8 H8 109.7 . . ?
C9 C8 S1 116.25(13) . . ?
C9 C8 C7 102.53(15) . . ?
C9 C8 H8 109.7 . . ?
C8 C9 H9 106.9 . . ?
C8 C9 C10 100.87(15) . . ?
C10 C9 H9 106.9 . . ?
C11 C9 C8 117.38(16) . . ?
C11 C9 H9 106.9 . . ?
C11 C9 C10 117.16(16) . . ?
N1 C10 C9 104.94(15) . . ?
N1 C10 H10 107.9 . . ?
N1 C10 C18 110.80(17) . . ?
C9 C10 H10 107.9 . . ?
C18 C10 C9 117.10(16) . . ?
C18 C10 H10 107.9 . . ?
C12 C11 C9 123.44(17) . . ?
C16 C11 C9 118.87(17) . . ?
C16 C11 C12 117.62(18) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.98(19) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.39(19) . . ?
C14 C13 H13 119.8 . . ?
O4 C14 C13 116.54(18) . . ?
O4 C14 C15 123.80(18) . . ?
C15 C14 C13 119.65(18) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.28(18) . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 122.07(18) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C10 121.16(17) . . ?
C19 C18 C23 118.84(18) . . ?
C23 C18 C10 119.73(17) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.01(18) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.8 . . ?
C21 C20 C19 118.43(19) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 N2 118.97(19) . . ?
C20 C21 C22 122.22(19) . . ?
C22 C21 N2 118.79(19) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 C21 118.42(18) . . ?
C23 C22 H22 120.8 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.02(18) . . ?
C22 C23 H23 119.5 . . ?

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 C2 -149.0(2) . . . . ?
S1 O1 C1 C6 34.5(3) . . . . ?
S1 C8 C9 C10 158.09(13) . . . . ?
S1 C8 C9 C11 -73.4(2) . . . . ?
O1 S1 C8 C7 -37.70(17) . . . . ?
O1 S1 C8 C9 -152.56(16) . . . . ?
O1 C1 C2 C3 -176.1(2) . . . . ?
O1 C1 C6 C5 177.9(2) . . . . ?
O1 C1 C6 C7 -2.7(3) . . . . ?
O2 S1 O1 C1 -127.0(2) . . . . ?
O2 S1 C8 C7 73.33(16) . . . . ?
O2 S1 C8 C9 -41.53(17) . . . . ?
O3 S1 O1 C1 106.9(2) . . . . ?
O3 S1 C8 C7 -152.99(14) . . . . ?
O3 S1 C8 C9 92.15(16) . . . . ?
O4 C14 C15 C16 180.00(18) . . . . ?
O5 N2 C21 C20 -26.6(3) . . . . ?
O5 N2 C21 C22 151.7(2) . . . . ?
O6 N2 C21 C20 153.8(2) . . . . ?
O6 N2 C21 C22 -27.8(3) . . . . ?
N1 C7 C8 S1 -168.57(14) . . . . ?
N1 C7 C8 C9 -45.05(19) . . . . ?
N1 C10 C18 C19 3.6(3) . . . . ?
N1 C10 C18 C23 -170.22(17) . . . . ?
N2 C21 C22 C23 -177.59(18) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C1 C6 C7 N1 -162.81(18) . . . . ?
C1 C6 C7 C8 -48.8(2) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -179.0(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
C4 C5 C6 C7 178.44(19) . . . . ?
C5 C6 C7 N1 16.5(3) . . . . ?
C5 C6 C7 C8 130.5(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C7 C8 S1 68.05(18) . . . . ?
C6 C7 C8 C9 -168.43(15) . . . . ?
C7 N1 C10 C9 -7.1(2) . . . . ?
C7 N1 C10 C18 -134.43(17) . . . . ?
C7 C8 C9 C10 39.89(17) . . . . ?
C7 C8 C9 C11 168.41(16) . . . . ?
C8 S1 O1 C1 -11.0(2) . . . . ?
C8 C9 C10 N1 -20.81(19) . . . . ?
C8 C9 C10 C18 102.52(18) . . . . ?
C8 C9 C11 C12 -39.9(3) . . . . ?
C8 C9 C11 C16 143.49(18) . . . . ?
C9 C10 C18 C19 -116.7(2) . . . . ?
C9 C10 C18 C23 69.5(2) . . . . ?
C9 C11 C12 C13 -175.74(18) . . . . ?
C9 C11 C16 C15 175.76(18) . . . . ?
C10 N1 C7 C6 150.21(17) . . . . ?
C10 N1 C7 C8 32.2(2) . . . . ?
C10 C9 C11 C12 80.4(2) . . . . ?
C10 C9 C11 C16 -96.2(2) . . . . ?
C10 C18 C19 C20 -172.53(18) . . . . ?
C10 C18 C23 C22 175.12(18) . . . . ?
C11 C9 C10 N1 -149.49(17) . . . . ?
C11 C9 C10 C18 -26.2(2) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C12 C13 C14 O4 179.83(19) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C16 C11 C12 C13 0.9(3) . . . . ?
C17 O4 C14 C13 -174.23(19) . . . . ?
C17 O4 C14 C15 6.3(3) . . . . ?
C18 C19 C20 C21 -2.7(3) . . . . ?
C19 C18 C23 C22 1.1(3) . . . . ?
C19 C20 C21 N2 -179.99(18) . . . . ?
C19 C20 C21 C22 1.7(3) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 C18 -2.2(3) . . . . ?
C23 C18 C19 C20 1.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2378446'
loop_
_audit_author_name
_audit_author_address
'we sd'
;SHIHEZI University
China
;
_audit_update_record             
;
2024-08-19 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2024-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O6 S'
_chemical_formula_sum            'C20 H21 N O6 S'
_chemical_formula_weight         403.44
_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      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                   10.0053(2)
_cell_length_b                   13.4636(3)
_cell_length_c                   15.1329(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.2020(10)
_cell_angle_gamma                90
_cell_volume                     1947.33(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6411
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      72.14
_cell_measurement_theta_min      4.49
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.749
_exptl_absorpt_coefficient_mu    1.803
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0909 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.8856.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14602
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.138
_diffrn_reflns_theta_min         4.488
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3132
_reflns_number_total             3807
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.036
_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)+(0.0439P)²+1.0314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1051
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_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 0.55197(5) 0.57208(4) 0.21030(3) 0.02897(13) Uani 1 1 d . . . . .
O1 O 0.51239(14) 0.68212(11) 0.23366(10) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.67206(16) 0.57691(12) 0.17824(10) 0.0379(4) Uani 1 1 d . . . . .
O3 O 0.42395(17) 0.53260(12) 0.15301(11) 0.0438(4) Uani 1 1 d . . . . .
O4 O 0.61347(15) 0.41334(11) 0.55226(10) 0.0349(3) Uani 1 1 d . . . . .
O5 O 0.69672(14) 0.27313(10) 0.50746(10) 0.0298(3) Uani 1 1 d . . . . .
O6 O 0.96790(13) 0.42983(11) 0.40661(9) 0.0294(3) Uani 1 1 d . . . . .
H6 H 1.047255 0.443198 0.442799 0.044 Uiso 1 1 calc R U . . .
N1 N 0.76495(15) 0.52866(12) 0.46975(11) 0.0237(3) Uani 1 1 d . . . . .
H1 H 0.706(2) 0.5424(17) 0.5002(16) 0.028 Uiso 1 1 d . U . . .
C1 C 0.60177(19) 0.73695(15) 0.30739(13) 0.0265(4) Uani 1 1 d . . . . .
C2 C 0.5825(2) 0.83849(16) 0.30067(14) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.517619 0.867093 0.247788 0.038 Uiso 1 1 calc R U . . .
C3 C 0.6593(2) 0.89782(16) 0.37238(16) 0.0363(5) Uani 1 1 d . . . . .
H3 H 0.647360 0.967860 0.368697 0.044 Uiso 1 1 calc R U . . .
C4 C 0.7536(2) 0.85582(17) 0.44964(16) 0.0374(5) Uani 1 1 d . . . . .
H4 H 0.804617 0.896835 0.499250 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7731(2) 0.75394(15) 0.45419(14) 0.0304(4) Uani 1 1 d . . . . .
H5 H 0.839367 0.725821 0.506699 0.036 Uiso 1 1 calc R U . . .
C6 C 0.69762(18) 0.69180(14) 0.38333(13) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.72529(17) 0.58234(14) 0.38095(12) 0.0233(4) Uani 1 1 d . . . . .
H7 H 0.802478 0.573212 0.352178 0.028 Uiso 1 1 calc R U . . .
C8 C 0.59899(18) 0.52343(14) 0.32333(13) 0.0240(4) Uani 1 1 d . . . . .
H8 H 0.519388 0.531955 0.349977 0.029 Uiso 1 1 calc R U . . .
C9 C 0.65217(17) 0.41657(14) 0.33816(12) 0.0228(4) Uani 1 1 d . . . . .
H9 H 0.715522 0.405968 0.298813 0.027 Uiso 1 1 calc R U . . .
C10 C 0.54318(18) 0.33503(15) 0.31536(13) 0.0254(4) Uani 1 1 d . . . . .
C11 C 0.41831(19) 0.34226(17) 0.33866(14) 0.0324(4) Uani 1 1 d . . . . .
H11 H 0.396989 0.401518 0.365787 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3254(2) 0.26298(19) 0.32221(16) 0.0401(5) Uani 1 1 d . . . . .
H12 H 0.241493 0.268004 0.339173 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3538(2) 0.17677(18) 0.28138(17) 0.0433(6) Uani 1 1 d . . . . .
H13 H 0.289900 0.122724 0.270470 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4758(2) 0.16988(18) 0.25659(18) 0.0438(5) Uani 1 1 d . . . . .
H14 H 0.495770 0.111086 0.228162 0.053 Uiso 1 1 calc R U . . .
C15 C 0.5691(2) 0.24889(16) 0.27323(15) 0.0344(5) Uani 1 1 d . . . . .
H15 H 0.652265 0.243741 0.255386 0.041 Uiso 1 1 calc R U . . .
C16 C 0.74824(17) 0.42159(14) 0.44395(12) 0.0227(4) Uani 1 1 d . . . . .
C17 C 0.67792(18) 0.37000(15) 0.50813(13) 0.0256(4) Uani 1 1 d . . . . .
C18 C 0.6254(2) 0.21160(16) 0.55957(16) 0.0375(5) Uani 1 1 d . . . . .
H18A H 0.523469 0.224556 0.538742 0.045 Uiso 1 1 calc R U . . .
H18B H 0.661432 0.226444 0.626514 0.045 Uiso 1 1 calc R U . . .
C19 C 0.6541(4) 0.1078(2) 0.5417(3) 0.0838(13) Uani 1 1 d . . . . .
H19A H 0.617317 0.094059 0.475351 0.126 Uiso 1 1 calc R U . . .
H19B H 0.608893 0.063751 0.575822 0.126 Uiso 1 1 calc R U . . .
H19C H 0.755367 0.096240 0.562156 0.126 Uiso 1 1 calc R U . . .
C20 C 0.89120(18) 0.37300(15) 0.45413(13) 0.0272(4) Uani 1 1 d . . . . .
H20A H 0.944693 0.368456 0.520465 0.033 Uiso 1 1 calc R U . . .
H20B H 0.877240 0.304841 0.428499 0.033 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 1.6000(15) . ?
S1 O2 1.4241(15) . ?
S1 O3 1.4205(16) . ?
S1 C8 1.7608(19) . ?
O1 C1 1.414(2) . ?
O4 C17 1.207(2) . ?
O5 C17 1.318(2) . ?
O5 C18 1.466(2) . ?
O6 H6 0.8400 . ?
O6 C20 1.420(2) . ?
N1 H1 0.87(2) . ?
N1 C7 1.473(2) . ?
N1 C16 1.490(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.399(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 C7 1.502(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.528(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.527(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.514(3) . ?
C9 C16 1.607(2) . ?
C10 C11 1.398(3) . ?
C10 C15 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.525(2) . ?
C16 C20 1.539(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.468(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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 C8 98.18(8) . . ?
O2 S1 O1 108.78(9) . . ?
O2 S1 C8 109.76(9) . . ?
O3 S1 O1 104.12(9) . . ?
O3 S1 O2 120.57(10) . . ?
O3 S1 C8 112.79(10) . . ?
C1 O1 S1 121.17(12) . . ?
C17 O5 C18 117.49(15) . . ?
C20 O6 H6 109.5 . . ?
C7 N1 H1 109.6(15) . . ?
C7 N1 C16 104.86(14) . . ?
C16 N1 H1 107.6(15) . . ?
C2 C1 O1 114.64(17) . . ?
C2 C1 C6 122.54(18) . . ?
C6 C1 O1 122.76(18) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.75(19) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.35(19) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 119.54(17) . . ?
C5 C6 C1 117.07(18) . . ?
C5 C6 C7 123.08(17) . . ?
N1 C7 C6 117.48(15) . . ?
N1 C7 H7 107.6 . . ?
N1 C7 C8 102.71(14) . . ?
C6 C7 H7 107.6 . . ?
C6 C7 C8 113.32(15) . . ?
C8 C7 H7 107.6 . . ?
S1 C8 H8 109.5 . . ?
C7 C8 S1 107.43(12) . . ?
C7 C8 H8 109.5 . . ?
C9 C8 S1 118.33(13) . . ?
C9 C8 C7 102.22(14) . . ?
C9 C8 H8 109.5 . . ?
C8 C9 H9 107.6 . . ?
C8 C9 C16 100.75(14) . . ?
C10 C9 C8 116.97(15) . . ?
C10 C9 H9 107.6 . . ?
C10 C9 C16 115.86(15) . . ?
C16 C9 H9 107.6 . . ?
C11 C10 C9 121.96(17) . . ?
C15 C10 C9 119.47(16) . . ?
C15 C10 C11 118.52(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 121.17(19) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
N1 C16 C9 106.83(14) . . ?
N1 C16 C17 108.12(14) . . ?
N1 C16 C20 110.87(15) . . ?
C17 C16 C9 111.27(14) . . ?
C17 C16 C20 109.45(15) . . ?
C20 C16 C9 110.27(14) . . ?
O4 C17 O5 125.68(18) . . ?
O4 C17 C16 123.70(18) . . ?
O5 C17 C16 110.61(15) . . ?
O5 C18 H18A 110.4 . . ?
O5 C18 H18B 110.4 . . ?
O5 C18 C19 106.64(19) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.4 . . ?
C19 C18 H18B 110.4 . . ?
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 . . ?
O6 C20 C16 110.22(15) . . ?
O6 C20 H20A 109.6 . . ?
O6 C20 H20B 109.6 . . ?
C16 C20 H20A 109.6 . . ?
C16 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 O1 C1 C2 158.50(14) . . . . ?
S1 O1 C1 C6 -24.4(2) . . . . ?
S1 C8 C9 C10 -80.14(18) . . . . ?
S1 C8 C9 C16 153.37(12) . . . . ?
O1 S1 C8 C7 -62.75(13) . . . . ?
O1 S1 C8 C9 -177.67(13) . . . . ?
O1 C1 C2 C3 176.13(16) . . . . ?
O1 C1 C6 C5 -175.93(16) . . . . ?
O1 C1 C6 C7 10.3(3) . . . . ?
O2 S1 O1 C1 -66.56(16) . . . . ?
O2 S1 C8 C7 50.65(15) . . . . ?
O2 S1 C8 C9 -64.27(15) . . . . ?
O3 S1 O1 C1 163.69(14) . . . . ?
O3 S1 C8 C7 -171.87(12) . . . . ?
O3 S1 C8 C9 73.20(15) . . . . ?
N1 C7 C8 S1 -173.80(11) . . . . ?
N1 C7 C8 C9 -48.56(16) . . . . ?
N1 C16 C17 O4 18.8(2) . . . . ?
N1 C16 C17 O5 -161.71(14) . . . . ?
N1 C16 C20 O6 -51.39(19) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 N1 -150.09(16) . . . . ?
C1 C6 C7 C8 -30.5(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -172.85(17) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 173.81(18) . . . . ?
C5 C6 C7 N1 36.5(2) . . . . ?
C5 C6 C7 C8 156.11(17) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C6 C7 C8 S1 58.44(17) . . . . ?
C6 C7 C8 C9 -176.32(14) . . . . ?
C7 N1 C16 C9 -17.37(16) . . . . ?
C7 N1 C16 C17 -137.22(14) . . . . ?
C7 N1 C16 C20 102.81(16) . . . . ?
C7 C8 C9 C10 162.15(15) . . . . ?
C7 C8 C9 C16 35.66(15) . . . . ?
C8 S1 O1 C1 47.61(15) . . . . ?
C8 C9 C10 C11 -41.4(3) . . . . ?
C8 C9 C10 C15 140.99(19) . . . . ?
C8 C9 C16 N1 -12.04(16) . . . . ?
C8 C9 C16 C17 105.76(16) . . . . ?
C8 C9 C16 C20 -132.59(15) . . . . ?
C9 C10 C11 C12 -175.57(19) . . . . ?
C9 C10 C15 C14 175.8(2) . . . . ?
C9 C16 C17 O4 -98.2(2) . . . . ?
C9 C16 C17 O5 81.27(18) . . . . ?
C9 C16 C20 O6 66.71(19) . . . . ?
C10 C9 C16 N1 -139.26(15) . . . . ?
C10 C9 C16 C17 -21.5(2) . . . . ?
C10 C9 C16 C20 100.18(18) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C10 C15 C14 -1.8(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
C15 C10 C11 C12 2.0(3) . . . . ?
C16 N1 C7 C6 165.48(14) . . . . ?
C16 N1 C7 C8 40.40(16) . . . . ?
C16 C9 C10 C11 77.2(2) . . . . ?
C16 C9 C10 C15 -100.4(2) . . . . ?
C17 O5 C18 C19 175.6(2) . . . . ?
C17 C16 C20 O6 -170.57(15) . . . . ?
C18 O5 C17 O4 4.5(3) . . . . ?
C18 O5 C17 C16 -174.91(15) . . . . ?
C20 C16 C17 O4 139.70(19) . . . . ?
C20 C16 C17 O5 -40.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_CCDC3
_audit_block_doi                 10.5517/ccdc.csd.cc2dgy1w
_database_code_depnum_ccdc_archive 'CCDC 2218888'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2022-2w3cr 2022
loop_
_audit_author_name
_audit_author_address
'we sd'
;SHIHEZI University
China
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N O7 S'
_chemical_formula_sum            'C22 H23 N O7 S'
_chemical_formula_weight         445.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.6166(3)
_cell_length_b                   10.0879(3)
_cell_length_c                   11.7837(4)
_cell_angle_alpha                73.3600(10)
_cell_angle_beta                 77.3780(10)
_cell_angle_gamma                84.3940(10)
_cell_volume                     1068.06(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9290
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.12
_cell_measurement_theta_min      4.58
_shelx_estimated_absorpt_T_max   0.712
_shelx_estimated_absorpt_T_min   0.671
_exptl_absorpt_coefficient_mu    1.735
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0938 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.8531. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25182
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.225
_diffrn_reflns_theta_min         4.578
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4031
_reflns_number_total             4164
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.081
_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)+(0.0395P)²+0.4936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H12C,H12D,H1} of C12A, All C(H,H) groups
 At 1.5 times of:
  {H13A,H13B,H13C} of C13, {H13D,H13E,H13F} of C13A, {H16A,H16B,H16C} of C16
2. Restrained distances
 O4-C12A = O4-C12
 1.45 with sigma of 0.01
 C13-C12 = C13A-C12A
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C13A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D), C15(H15A,H15B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22323(15) 0.96291(15) 0.48563(13) 0.0286(3) Uani 1 1 d . . . . .
C2 C 0.17369(17) 1.05956(16) 0.39246(14) 0.0360(3) Uani 1 1 d . . . . .
H2 H 0.190511 1.155041 0.376459 0.043 Uiso 1 1 calc R . . . .
C3 C 0.09948(17) 1.01556(17) 0.32299(14) 0.0374(4) Uani 1 1 d . . . . .
H3 H 0.063804 1.081193 0.259321 0.045 Uiso 1 1 calc R . . . .
C4 C 0.07669(16) 0.87581(17) 0.34568(14) 0.0349(3) Uani 1 1 d . . . . .
H4 H 0.025347 0.845904 0.297743 0.042 Uiso 1 1 calc R . . . .
C5 C 0.12890(15) 0.77999(15) 0.43833(13) 0.0300(3) Uani 1 1 d . . . . .
H5 H 0.114027 0.684353 0.452769 0.036 Uiso 1 1 calc R . . . .
C6 C 0.20290(14) 0.82184(14) 0.51063(12) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.25076(14) 0.72449(14) 0.61821(12) 0.0249(3) Uani 1 1 d . . . . .
H7 H 0.173769 0.725168 0.690471 0.030 Uiso 1 1 calc R . . . .
C8 C 0.38745(14) 0.77238(14) 0.64042(12) 0.0252(3) Uani 1 1 d . . . . .
H8 H 0.461630 0.787475 0.564302 0.030 Uiso 1 1 calc R . . . .
C9 C 0.35135(14) 0.52658(14) 0.72409(12) 0.0245(3) Uani 1 1 d . . . . .
C10 C 0.43599(14) 0.64882(14) 0.73667(12) 0.0254(3) Uani 1 1 d . . . . .
H10 H 0.400308 0.663990 0.818477 0.031 Uiso 1 1 calc R . . . .
C11 C 0.23147(15) 0.47782(15) 0.83589(13) 0.0318(3) Uani 1 1 d . . . . .
C12 C 0.0550(3) 0.2971(3) 0.9187(3) 0.0372(8) Uani 0.677(7) 1 d D . P A 1
H12A H -0.021862 0.279588 0.881637 0.045 Uiso 0.677(7) 1 calc R . P A 1
H12B H 0.013992 0.351799 0.976571 0.045 Uiso 0.677(7) 1 calc R . P A 1
C12A C 0.0894(8) 0.3067(7) 0.9566(6) 0.0371(17) Uani 0.323(7) 1 d D . P A 2
H12C H 0.155748 0.277206 1.013445 0.045 Uiso 0.323(7) 1 calc R . P A 2
H12D H 0.014526 0.370941 0.985314 0.045 Uiso 0.323(7) 1 calc R . P A 2
H1 H 0.350(2) 0.574(2) 0.5532(18) 0.045 Uiso 1 1 d R . . . .
C13 C 0.1199(4) 0.1646(3) 0.9814(3) 0.0587(11) Uani 0.677(7) 1 d D . P A 1
H13A H 0.160334 0.111719 0.923027 0.088 Uiso 0.677(7) 1 calc GR . P A 1
H13B H 0.046729 0.110800 1.044770 0.088 Uiso 0.677(7) 1 calc GR . P A 1
H13C H 0.195616 0.183478 1.017743 0.088 Uiso 0.677(7) 1 calc GR . P A 1
C13A C 0.0267(9) 0.1852(8) 0.9393(6) 0.064(3) Uani 0.323(7) 1 d D U P A 2
H13D H -0.029064 0.217575 0.875466 0.096 Uiso 0.323(7) 1 calc GR . P A 2
H13E H -0.035472 0.137697 1.014935 0.096 Uiso 0.323(7) 1 calc GR . P A 2
H13F H 0.103580 0.121065 0.916057 0.096 Uiso 0.323(7) 1 calc GR . P A 2
C14 C 0.44852(14) 0.39969(14) 0.71421(12) 0.0250(3) Uani 1 1 d . . . . .
C15 C 0.5828(2) 0.21910(19) 0.82624(16) 0.0458(4) Uani 1 1 d . . . . .
H15A H 0.671268 0.246900 0.765495 0.055 Uiso 1 1 calc R . . . .
H15B H 0.542609 0.141869 0.809121 0.055 Uiso 1 1 calc R . . . .
C16 C 0.6139(3) 0.1755(2) 0.9505(2) 0.0649(6) Uani 1 1 d . . . . .
H16A H 0.680442 0.094823 0.958047 0.097 Uiso 1 1 calc GR . . . .
H16B H 0.525100 0.151154 1.009812 0.097 Uiso 1 1 calc GR . . . .
H16C H 0.656694 0.251689 0.965225 0.097 Uiso 1 1 calc GR . . . .
C17 C 0.59651(14) 0.62338(14) 0.71664(12) 0.0257(3) Uani 1 1 d . . . . .
C18 C 0.66745(16) 0.59901(16) 0.81200(13) 0.0332(3) Uani 1 1 d . . . . .
H18 H 0.615900 0.603442 0.889476 0.040 Uiso 1 1 calc R . . . .
C19 C 0.81365(17) 0.56811(18) 0.79468(15) 0.0382(4) Uani 1 1 d . . . . .
H19 H 0.861192 0.552483 0.860305 0.046 Uiso 1 1 calc R . . . .
C20 C 0.89015(16) 0.56001(16) 0.68284(15) 0.0347(3) Uani 1 1 d . . . . .
H20 H 0.989529 0.537340 0.671699 0.042 Uiso 1 1 calc R . . . .
C21 C 0.82043(15) 0.58527(15) 0.58730(13) 0.0301(3) Uani 1 1 d . . . . .
H21 H 0.872358 0.580441 0.510039 0.036 Uiso 1 1 calc R . . . .
C22 C 0.67505(15) 0.61763(14) 0.60362(12) 0.0268(3) Uani 1 1 d . . . . .
H22 H 0.628592 0.636039 0.537067 0.032 Uiso 1 1 calc R . . . .
N1 N 0.28414(12) 0.58022(12) 0.61838(10) 0.0246(2) Uani 1 1 d . . . . .
O1 O 0.21930(12) 0.91835(12) 0.76958(10) 0.0412(3) Uani 1 1 d . . . . .
O2 O 0.30043(12) 1.01850(11) 0.55001(10) 0.0375(3) Uani 1 1 d . . . . .
O3 O 0.46207(13) 0.99920(13) 0.68217(13) 0.0487(3) Uani 1 1 d . . . . .
O4 O 0.16861(12) 0.37150(12) 0.82593(11) 0.0460(3) Uani 1 1 d D . . . .
O5 O 0.20036(14) 0.52914(14) 0.91840(11) 0.0517(3) Uani 1 1 d . . . . .
O6 O 0.47996(11) 0.33600(10) 0.82146(9) 0.0315(2) Uani 1 1 d . . . . .
O7 O 0.49220(11) 0.36557(10) 0.62271(9) 0.0300(2) Uani 1 1 d . . . . .
S1 S 0.34239(4) 0.93217(4) 0.67525(3) 0.03207(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(2) . ?
C1 C6 1.3926(19) . ?
C1 O2 1.4186(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C6 C7 1.4957(18) . ?
C7 H7 1.0000 . ?
C7 C8 1.5416(19) . ?
C7 N1 1.4589(17) . ?
C8 H8 1.0000 . ?
C8 C10 1.5382(18) . ?
C8 S1 1.7661(13) . ?
C9 C10 1.5996(19) . ?
C9 C11 1.5436(18) . ?
C9 C14 1.5262(18) . ?
C9 N1 1.4696(17) . ?
C10 H10 1.0000 . ?
C10 C17 1.5174(19) . ?
C11 O4 1.326(2) . ?
C11 O5 1.1973(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.482(4) . ?
C12 O4 1.456(3) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C12A C13A 1.499(7) . ?
C12A O4 1.545(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14 O6 1.3287(16) . ?
C14 O7 1.2016(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.491(3) . ?
C15 O6 1.4596(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3901(19) . ?
C17 C22 1.3942(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(2) . ?
C22 H22 0.9500 . ?
N1 H1 0.89(2) . ?
O1 S1 1.4229(12) . ?
O2 S1 1.5983(11) . ?
O3 S1 1.4188(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.18(14) . . ?
C2 C1 O2 114.64(13) . . ?
C6 C1 O2 123.14(13) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.09(14) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.28(14) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.91(14) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.95(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.58(13) . . ?
C1 C6 C7 119.07(12) . . ?
C5 C6 C7 123.18(12) . . ?
C6 C7 H7 107.4 . . ?
C6 C7 C8 111.63(11) . . ?
C8 C7 H7 107.4 . . ?
N1 C7 C6 118.57(11) . . ?
N1 C7 H7 107.4 . . ?
N1 C7 C8 103.95(10) . . ?
C7 C8 H8 108.9 . . ?
C7 C8 S1 106.51(9) . . ?
C10 C8 C7 104.31(11) . . ?
C10 C8 H8 108.9 . . ?
C10 C8 S1 118.79(9) . . ?
S1 C8 H8 108.9 . . ?
C11 C9 C10 111.04(11) . . ?
C14 C9 C10 111.89(11) . . ?
C14 C9 C11 106.52(11) . . ?
N1 C9 C10 108.29(10) . . ?
N1 C9 C11 107.57(11) . . ?
N1 C9 C14 111.47(11) . . ?
C8 C10 C9 100.95(10) . . ?
C8 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
C17 C10 C8 113.55(11) . . ?
C17 C10 C9 113.92(11) . . ?
C17 C10 H10 109.4 . . ?
O4 C11 C9 109.61(12) . . ?
O5 C11 C9 124.79(15) . . ?
O5 C11 O4 125.60(14) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
O4 C12 H12A 110.4 . . ?
O4 C12 H12B 110.4 . . ?
O4 C12 C13 106.7(3) . . ?
H12C C12A H12D 109.5 . . ?
C13A C12A H12C 111.8 . . ?
C13A C12A H12D 111.8 . . ?
C13A C12A O4 100.0(5) . . ?
O4 C12A H12C 111.8 . . ?
O4 C12A H12D 111.8 . . ?
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 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O6 C14 C9 109.29(11) . . ?
O7 C14 C9 124.95(12) . . ?
O7 C14 O6 125.73(13) . . ?
H15A C15 H15B 108.6 . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
O6 C15 H15A 110.3 . . ?
O6 C15 H15B 110.3 . . ?
O6 C15 C16 107.08(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C10 120.63(12) . . ?
C18 C17 C22 118.58(13) . . ?
C22 C17 C10 120.73(12) . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.43(14) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.58(14) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.28(14) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.42(14) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.70(13) . . ?
C21 C22 H22 119.7 . . ?
C7 N1 C9 102.31(10) . . ?
C7 N1 H1 110.8(13) . . ?
C9 N1 H1 107.4(13) . . ?
C1 O2 S1 123.27(9) . . ?
C11 O4 C12 123.6(2) . . ?
C11 O4 C12A 103.1(3) . . ?
C14 O6 C15 116.68(11) . . ?
O1 S1 C8 109.75(7) . . ?
O1 S1 O2 109.51(7) . . ?
O2 S1 C8 98.09(6) . . ?
O3 S1 C8 113.27(7) . . ?
O3 S1 O1 119.35(8) . . ?
O3 S1 O2 104.51(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
