# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2338400'
loop_
_audit_author_name
_audit_author_address
'Quan Zhou'
;Taizhou university
China
;
_audit_update_record             
;
2024-03-07 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 N2 O5 S'
_chemical_formula_weight         490.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.2688(3)
_cell_length_b                   13.6128(4)
_cell_length_c                   21.1249(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.7870(10)
_cell_angle_gamma                90
_cell_volume                     2377.63(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.65

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36969
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4177
_reflns_number_gt                3639
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+0.5984P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4177
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S001 S 0.55788(5) 0.49287(3) 0.81310(2) 0.03873(14) Uani 1 1 d . . . . .
O3 O 0.42996(13) 0.35880(9) 0.71456(6) 0.0482(3) Uani 1 1 d . . . . .
O4 O 0.92575(14) 0.39991(10) 0.70100(6) 0.0517(3) Uani 1 1 d . . . . .
O1 O 0.67971(15) 0.55481(10) 0.84048(6) 0.0544(3) Uani 1 1 d . . . . .
O2 O 0.48300(17) 0.42308(9) 0.85314(6) 0.0551(3) Uani 1 1 d . . . . .
N2 N 0.94246(15) 0.28985(10) 0.62072(6) 0.0380(3) Uani 1 1 d . . . . .
O5 O 1.30576(17) 0.26318(11) 0.51315(6) 0.0657(4) Uani 1 1 d . . . . .
N1 N 0.65179(16) 0.43321(9) 0.75633(6) 0.0387(3) Uani 1 1 d . . . . .
H1 H 0.7545 0.4411 0.7530 0.046 Uiso 1 1 calc R U . . .
C11 C 0.68248(18) 0.32164(10) 0.66782(7) 0.0339(3) Uani 1 1 d . . . . .
C10 C 0.57464(18) 0.37158(11) 0.71416(7) 0.0359(3) Uani 1 1 d . . . . .
C7 C 0.46785(19) 0.63387(11) 0.72799(7) 0.0382(4) Uani 1 1 d . . . . .
C6 C 0.41117(18) 0.56451(10) 0.77194(7) 0.0336(3) Uani 1 1 d . . . . .
C13 C 0.61338(19) 0.25495(11) 0.62862(7) 0.0375(3) Uani 1 1 d . . . . .
H13 H 0.5030 0.2428 0.6314 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7046(2) 0.20308(11) 0.58334(7) 0.0388(4) Uani 1 1 d . . . . .
C12 C 0.85579(19) 0.34085(11) 0.66538(7) 0.0372(3) Uani 1 1 d . . . . .
C4 C 0.24478(19) 0.55204(11) 0.78269(8) 0.0382(4) Uani 1 1 d . . . . .
C19 C 0.8711(2) 0.22250(11) 0.57908(7) 0.0396(4) Uani 1 1 d . . . . .
C3 C 0.1389(2) 0.61107(12) 0.74877(9) 0.0467(4) Uani 1 1 d . . . . .
H3 H 0.0287 0.6048 0.7560 0.056 Uiso 1 1 calc R U . . .
C20 C 1.12090(19) 0.30673(13) 0.62051(8) 0.0443(4) Uani 1 1 d . . . . .
H20A H 1.1746 0.2452 0.6109 0.053 Uiso 1 1 calc R U . . .
H20B H 1.1558 0.3269 0.6626 0.053 Uiso 1 1 calc R U . . .
C8 C 0.3531(2) 0.68868(12) 0.69489(8) 0.0442(4) Uani 1 1 d . . . . .
H8 H 0.3882 0.7337 0.6650 0.053 Uiso 1 1 calc R U . . .
C21 C 1.17330(19) 0.38327(14) 0.57350(8) 0.0453(4) Uani 1 1 d . . . . .
C2 C 0.1893(2) 0.67918(12) 0.70446(8) 0.0459(4) Uani 1 1 d . . . . .
C26 C 1.2639(2) 0.36032(15) 0.52035(8) 0.0518(4) Uani 1 1 d . . . . .
C15 C 0.6322(2) 0.13363(13) 0.54276(8) 0.0503(4) Uani 1 1 d . . . . .
H15 H 0.5228 0.1192 0.5467 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9600(2) 0.17360(14) 0.53270(9) 0.0532(5) Uani 1 1 d . . . . .
H18 H 1.0703 0.1853 0.5291 0.064 Uiso 1 1 calc R U . . .
C9 C 0.6434(2) 0.65312(14) 0.71458(10) 0.0545(5) Uani 1 1 d . . . . .
H9A H 0.7024 0.6594 0.7538 0.082 Uiso 1 1 calc R U . . .
H9B H 0.6530 0.7128 0.6907 0.082 Uiso 1 1 calc R U . . .
H9C H 0.6866 0.5994 0.6907 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1704(2) 0.47932(14) 0.82774(10) 0.0554(5) Uani 1 1 d . . . . .
H5A H 0.1973 0.4138 0.8149 0.083 Uiso 1 1 calc R U . . .
H5B H 0.0550 0.4871 0.8272 0.083 Uiso 1 1 calc R U . . .
H5C H 0.2115 0.4909 0.8698 0.083 Uiso 1 1 calc R U . . .
C22 C 1.1356(3) 0.48152(15) 0.58333(11) 0.0616(5) Uani 1 1 d . . . . .
H22 H 1.0773 0.4989 0.6190 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8839(3) 0.10830(14) 0.49255(9) 0.0603(5) Uani 1 1 d . . . . .
H17 H 0.9436 0.0776 0.4612 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7205(3) 0.08700(14) 0.49749(9) 0.0606(5) Uani 1 1 d . . . . .
H16 H 0.6717 0.0417 0.4704 0.073 Uiso 1 1 calc R U . . .
C1 C 0.0682(3) 0.74036(16) 0.66820(11) 0.0703(6) Uani 1 1 d . . . . .
H1A H -0.0007 0.6982 0.6433 0.105 Uiso 1 1 calc R U . . .
H1B H 0.1241 0.7848 0.6408 0.105 Uiso 1 1 calc R U . . .
H1C H 0.0039 0.7772 0.6973 0.105 Uiso 1 1 calc R U . . .
C25 C 1.3107(3) 0.4330(2) 0.47865(10) 0.0693(6) Uani 1 1 d . . . . .
H25 H 1.3699 0.4166 0.4431 0.083 Uiso 1 1 calc R U . . .
C24 C 1.2699(3) 0.5291(2) 0.48970(12) 0.0777(7) Uani 1 1 d . . . . .
H24 H 1.3022 0.5777 0.4616 0.093 Uiso 1 1 calc R U . . .
C23 C 1.1821(3) 0.55403(18) 0.54166(13) 0.0771(7) Uani 1 1 d . . . . .
H23 H 1.1541 0.6192 0.5489 0.093 Uiso 1 1 calc R U . . .
C27 C 1.3471(3) 0.2305(2) 0.45134(10) 0.0923(9) Uani 1 1 d . . . . .
H27A H 1.2645 0.2504 0.4216 0.138 Uiso 1 1 calc R U . . .
H27B H 1.3561 0.1602 0.4512 0.138 Uiso 1 1 calc R U . . .
H27C H 1.4486 0.2589 0.4395 0.138 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
S001 O2 1.4198(13) . ?
S001 O1 1.4298(13) . ?
S001 N1 1.6511(13) . ?
S001 C6 1.7747(15) . ?
O3 C10 1.2090(19) . ?
O4 C12 1.2390(19) . ?
N2 C12 1.3800(19) . ?
N2 C19 1.396(2) . ?
N2 C20 1.493(2) . ?
O5 C26 1.376(2) . ?
O5 C27 1.425(2) . ?
N1 C10 1.374(2) . ?
N1 H1 0.8600 . ?
C11 C13 1.350(2) . ?
C11 C12 1.458(2) . ?
C11 C10 1.496(2) . ?
C7 C8 1.389(2) . ?
C7 C6 1.409(2) . ?
C7 C9 1.506(2) . ?
C6 C4 1.408(2) . ?
C13 C14 1.415(2) . ?
C13 H13 0.9300 . ?
C14 C19 1.406(2) . ?
C14 C15 1.405(2) . ?
C4 C3 1.381(2) . ?
C4 C5 1.510(2) . ?
C19 C18 1.401(2) . ?
C3 C2 1.386(3) . ?
C3 H3 0.9300 . ?
C20 C21 1.507(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C8 C2 1.378(3) . ?
C8 H8 0.9300 . ?
C21 C22 1.390(3) . ?
C21 C26 1.394(2) . ?
C2 C1 1.504(2) . ?
C26 C25 1.383(3) . ?
C15 C16 1.367(3) . ?
C15 H15 0.9300 . ?
C18 C17 1.375(3) . ?
C18 H18 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C17 C16 1.388(3) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C25 C24 1.372(4) . ?
C25 H25 0.9300 . ?
C24 C23 1.367(3) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S001 O1 117.66(8) . . ?
O2 S001 N1 108.47(7) . . ?
O1 S001 N1 104.36(7) . . ?
O2 S001 C6 111.03(8) . . ?
O1 S001 C6 110.32(7) . . ?
N1 S001 C6 103.86(7) . . ?
C12 N2 C19 122.83(13) . . ?
C12 N2 C20 116.55(13) . . ?
C19 N2 C20 120.57(13) . . ?
C26 O5 C27 117.71(18) . . ?
C10 N1 S001 123.53(11) . . ?
C10 N1 H1 118.2 . . ?
S001 N1 H1 118.2 . . ?
C13 C11 C12 120.44(14) . . ?
C13 C11 C10 117.11(14) . . ?
C12 C11 C10 122.43(13) . . ?
O3 C10 N1 122.27(14) . . ?
O3 C10 C11 122.53(14) . . ?
N1 C10 C11 115.20(13) . . ?
C8 C7 C6 117.44(15) . . ?
C8 C7 C9 117.76(15) . . ?
C6 C7 C9 124.81(15) . . ?
C7 C6 C4 121.44(14) . . ?
C7 C6 S001 117.37(11) . . ?
C4 C6 S001 121.18(12) . . ?
C11 C13 C14 121.67(15) . . ?
C11 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C19 C14 C15 119.81(15) . . ?
C19 C14 C13 118.75(14) . . ?
C15 C14 C13 121.44(16) . . ?
O4 C12 N2 119.94(14) . . ?
O4 C12 C11 123.07(14) . . ?
N2 C12 C11 116.98(13) . . ?
C3 C4 C6 117.39(15) . . ?
C3 C4 C5 116.58(15) . . ?
C6 C4 C5 126.03(15) . . ?
N2 C19 C18 122.08(16) . . ?
N2 C19 C14 119.29(14) . . ?
C18 C19 C14 118.63(15) . . ?
C4 C3 C2 123.04(16) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
N2 C20 C21 113.66(13) . . ?
N2 C20 H20A 108.8 . . ?
C21 C20 H20A 108.8 . . ?
N2 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C2 C8 C7 122.81(16) . . ?
C2 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C22 C21 C26 117.41(18) . . ?
C22 C21 C20 119.99(16) . . ?
C26 C21 C20 122.58(17) . . ?
C8 C2 C3 117.86(15) . . ?
C8 C2 C1 121.47(18) . . ?
C3 C2 C1 120.67(18) . . ?
O5 C26 C25 122.93(18) . . ?
O5 C26 C21 116.32(17) . . ?
C25 C26 C21 120.7(2) . . ?
C16 C15 C14 120.79(18) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C18 C19 119.91(19) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C23 C22 C21 121.8(2) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C18 C17 C16 121.75(18) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C15 C16 C17 119.06(17) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C24 C25 C26 120.1(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C23 C24 C25 120.5(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C23 C22 119.4(2) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S001 N1 C10 59.65(14) . . . . ?
O1 S001 N1 C10 -174.15(12) . . . . ?
C6 S001 N1 C10 -58.53(14) . . . . ?
S001 N1 C10 O3 2.2(2) . . . . ?
S001 N1 C10 C11 -177.82(10) . . . . ?
C13 C11 C10 O3 -4.8(2) . . . . ?
C12 C11 C10 O3 176.89(15) . . . . ?
C13 C11 C10 N1 175.23(13) . . . . ?
C12 C11 C10 N1 -3.1(2) . . . . ?
C8 C7 C6 C4 -0.9(2) . . . . ?
C9 C7 C6 C4 178.80(15) . . . . ?
C8 C7 C6 S001 178.82(11) . . . . ?
C9 C7 C6 S001 -1.5(2) . . . . ?
O2 S001 C6 C7 -177.00(11) . . . . ?
O1 S001 C6 C7 50.73(13) . . . . ?
N1 S001 C6 C7 -60.61(13) . . . . ?
O2 S001 C6 C4 2.72(15) . . . . ?
O1 S001 C6 C4 -129.55(13) . . . . ?
N1 S001 C6 C4 119.12(12) . . . . ?
C12 C11 C13 C14 -1.2(2) . . . . ?
C10 C11 C13 C14 -179.58(13) . . . . ?
C11 C13 C14 C19 -0.5(2) . . . . ?
C11 C13 C14 C15 179.87(15) . . . . ?
C19 N2 C12 O4 -179.85(15) . . . . ?
C20 N2 C12 O4 2.8(2) . . . . ?
C19 N2 C12 C11 0.0(2) . . . . ?
C20 N2 C12 C11 -177.37(13) . . . . ?
C13 C11 C12 O4 -178.67(15) . . . . ?
C10 C11 C12 O4 -0.4(2) . . . . ?
C13 C11 C12 N2 1.5(2) . . . . ?
C10 C11 C12 N2 179.72(13) . . . . ?
C7 C6 C4 C3 -0.5(2) . . . . ?
S001 C6 C4 C3 179.80(12) . . . . ?
C7 C6 C4 C5 179.07(15) . . . . ?
S001 C6 C4 C5 -0.6(2) . . . . ?
C12 N2 C19 C18 177.98(15) . . . . ?
C20 N2 C19 C18 -4.7(2) . . . . ?
C12 N2 C19 C14 -1.7(2) . . . . ?
C20 N2 C19 C14 175.58(14) . . . . ?
C15 C14 C19 N2 -178.41(14) . . . . ?
C13 C14 C19 N2 1.9(2) . . . . ?
C15 C14 C19 C18 1.9(2) . . . . ?
C13 C14 C19 C18 -177.76(15) . . . . ?
C6 C4 C3 C2 1.5(2) . . . . ?
C5 C4 C3 C2 -178.15(16) . . . . ?
C12 N2 C20 C21 -95.61(17) . . . . ?
C19 N2 C20 C21 86.93(18) . . . . ?
C6 C7 C8 C2 1.5(2) . . . . ?
C9 C7 C8 C2 -178.26(16) . . . . ?
N2 C20 C21 C22 69.6(2) . . . . ?
N2 C20 C21 C26 -112.36(18) . . . . ?
C7 C8 C2 C3 -0.6(3) . . . . ?
C7 C8 C2 C1 179.45(16) . . . . ?
C4 C3 C2 C8 -0.9(3) . . . . ?
C4 C3 C2 C1 179.02(17) . . . . ?
C27 O5 C26 C25 -22.6(3) . . . . ?
C27 O5 C26 C21 158.8(2) . . . . ?
C22 C21 C26 O5 177.23(17) . . . . ?
C20 C21 C26 O5 -0.9(2) . . . . ?
C22 C21 C26 C25 -1.3(3) . . . . ?
C20 C21 C26 C25 -179.44(17) . . . . ?
C19 C14 C15 C16 -2.3(3) . . . . ?
C13 C14 C15 C16 177.29(16) . . . . ?
N2 C19 C18 C17 -179.62(16) . . . . ?
C14 C19 C18 C17 0.1(3) . . . . ?
C26 C21 C22 C23 1.4(3) . . . . ?
C20 C21 C22 C23 179.58(19) . . . . ?
C19 C18 C17 C16 -1.7(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C18 C17 C16 C15 1.2(3) . . . . ?
O5 C26 C25 C24 -177.6(2) . . . . ?
C21 C26 C25 C24 0.8(3) . . . . ?
C26 C25 C24 C23 -0.3(4) . . . . ?
C25 C24 C23 C22 0.4(4) . . . . ?
C21 C22 C23 C24 -1.0(4) . . . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2349950'
loop_
_audit_author_name
_audit_author_address
obc
;Taizhou university
China
;
_audit_update_record             
;
2024-04-22 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N2 O4 S'
_chemical_formula_weight         341.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

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                   20.643(6)
_cell_length_b                   5.4637(13)
_cell_length_c                   28.909(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.269(9)
_cell_angle_gamma                90
_cell_volume                     3173.5(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2032
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      25.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7564
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.749
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2792
_reflns_number_gt                2005
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+1.8581P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2792
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000

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 0.25130(4) 1.01837(14) 0.13161(3) 0.0544(3) Uani 1 1 d . U . . .
O4 O 0.24678(8) 0.5168(3) 0.02902(6) 0.0454(5) Uani 1 1 d . . . . .
O3 O 0.12096(10) 1.0611(4) 0.05833(7) 0.0630(6) Uani 1 1 d . . . . .
O1 O 0.31354(9) 0.8992(5) 0.15025(8) 0.0756(7) Uani 1 1 d . U . . .
O2 O 0.25045(12) 1.2701(4) 0.11968(7) 0.0750(7) Uani 1 1 d . . . . .
N2 N 0.16573(9) 0.3690(4) -0.02988(7) 0.0386(5) Uani 1 1 d . . . . .
N1 N 0.21786(11) 0.8573(5) 0.08433(8) 0.0557(6) Uani 1 1 d . . . . .
H1 H 0.2408 0.7348 0.0783 0.067 Uiso 1 1 calc R U . . .
C10 C 0.18769(12) 0.5295(5) 0.00580(8) 0.0374(6) Uani 1 1 d . . . . .
C11 C 0.10112(11) 0.3606(5) -0.05763(8) 0.0373(6) Uani 1 1 d . . . . .
C16 C 0.05507(12) 0.5347(5) -0.04980(9) 0.0401(6) Uani 1 1 d . . . . .
C17 C 0.07730(13) 0.7089(5) -0.01298(9) 0.0436(7) Uani 1 1 d . . . . .
H17 H 0.0474 0.8267 -0.0075 0.052 Uiso 1 1 calc R U . . .
C9 C 0.13995(12) 0.7108(5) 0.01438(8) 0.0376(6) Uani 1 1 d . . . . .
C5 C 0.19943(12) 0.9764(5) 0.17137(8) 0.0427(6) Uani 1 1 d . . . . .
C12 C 0.08296(13) 0.1802(5) -0.09186(9) 0.0467(7) Uani 1 1 d . . . . .
H12 H 0.1139 0.0655 -0.0968 0.056 Uiso 1 1 calc R U . . .
C6 C 0.15346(14) 1.1520(5) 0.17550(10) 0.0520(7) Uani 1 1 d . . . . .
H6 H 0.1464 1.2861 0.1551 0.062 Uiso 1 1 calc R U . . .
C8 C 0.15781(14) 0.8948(5) 0.05330(9) 0.0467(7) Uani 1 1 d . . . . .
C4 C 0.20917(14) 0.7743(5) 0.20084(10) 0.0527(7) Uani 1 1 d . . . . .
H4 H 0.2396 0.6538 0.1975 0.063 Uiso 1 1 calc R U . . .
C15 C -0.01036(13) 0.5248(6) -0.07796(10) 0.0532(7) Uani 1 1 d . . . . .
H15 H -0.0416 0.6401 -0.0737 0.064 Uiso 1 1 calc R U . . .
C14 C -0.02790(13) 0.3466(6) -0.11143(10) 0.0578(8) Uani 1 1 d . . . . .
H14 H -0.0712 0.3403 -0.1298 0.069 Uiso 1 1 calc R U . . .
C13 C 0.01864(14) 0.1732(6) -0.11834(10) 0.0557(8) Uani 1 1 d . . . . .
H13 H 0.0059 0.0516 -0.1411 0.067 Uiso 1 1 calc R U . . .
C2 C 0.12809(15) 0.9309(7) 0.24102(10) 0.0612(9) Uani 1 1 d . . . . .
C7 C 0.11795(15) 1.1266(6) 0.21028(11) 0.0619(8) Uani 1 1 d . . . . .
H7 H 0.0865 1.2443 0.2130 0.074 Uiso 1 1 calc R U . . .
C3 C 0.17318(15) 0.7545(6) 0.23518(10) 0.0614(8) Uani 1 1 d . . . . .
H3 H 0.1794 0.6183 0.2550 0.074 Uiso 1 1 calc R U . . .
C1 C 0.09290(18) 0.9133(10) 0.28119(12) 0.1024(15) Uani 1 1 d . . . . .
H1A H 0.1247 0.9295 0.3110 0.154 Uiso 1 1 calc R U . . .
H1B H 0.0711 0.7575 0.2800 0.154 Uiso 1 1 calc R U . . .
H1C H 0.0605 1.0418 0.2782 0.154 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 O2 1.417(2) . ?
S1 O1 1.431(2) . ?
S1 N1 1.639(2) . ?
S1 C5 1.756(3) . ?
O4 C10 1.252(3) . ?
O3 C8 1.215(3) . ?
N2 C10 1.350(3) . ?
N2 C11 1.391(3) . ?
N1 C8 1.368(3) . ?
N1 H1 0.8600 . ?
C10 C9 1.458(3) . ?
C11 C12 1.386(4) . ?
C11 C16 1.399(3) . ?
C16 C15 1.409(3) . ?
C16 C17 1.423(4) . ?
C17 C9 1.352(3) . ?
C17 H17 0.9300 . ?
C9 C8 1.491(4) . ?
C5 C6 1.374(4) . ?
C5 C4 1.381(4) . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C4 C3 1.374(4) . ?
C4 H4 0.9300 . ?
C15 C14 1.362(4) . ?
C15 H15 0.9300 . ?
C14 C13 1.396(4) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C2 C7 1.375(5) . ?
C2 C3 1.377(5) . ?
C2 C1 1.508(4) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.56(15) . . ?
O2 S1 N1 109.79(14) . . ?
O1 S1 N1 103.87(13) . . ?
O2 S1 C5 108.09(13) . . ?
O1 S1 C5 108.89(13) . . ?
N1 S1 C5 105.81(12) . . ?
C10 N2 C11 124.8(2) . . ?
C8 N1 S1 127.7(2) . . ?
C8 N1 H1 116.2 . . ?
S1 N1 H1 116.2 . . ?
O4 C10 N2 119.2(2) . . ?
O4 C10 C9 124.0(2) . . ?
N2 C10 C9 116.7(2) . . ?
C12 C11 N2 120.1(2) . . ?
C12 C11 C16 121.1(2) . . ?
N2 C11 C16 118.8(2) . . ?
C11 C16 C15 118.5(2) . . ?
C11 C16 C17 117.5(2) . . ?
C15 C16 C17 124.0(2) . . ?
C9 C17 C16 122.9(2) . . ?
C9 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C17 C9 C10 119.2(2) . . ?
C17 C9 C8 119.0(2) . . ?
C10 C9 C8 121.8(2) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 S1 120.2(2) . . ?
C4 C5 S1 118.9(2) . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
O3 C8 N1 122.1(3) . . ?
O3 C8 C9 122.8(2) . . ?
N1 C8 C9 115.1(2) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C7 C2 C3 118.2(3) . . ?
C7 C2 C1 121.2(4) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C7 C6 121.4(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 -50.8(3) . . . . ?
O1 S1 N1 C8 -179.8(2) . . . . ?
C5 S1 N1 C8 65.6(3) . . . . ?
C11 N2 C10 O4 178.7(2) . . . . ?
C11 N2 C10 C9 -2.0(3) . . . . ?
C10 N2 C11 C12 -176.8(2) . . . . ?
C10 N2 C11 C16 2.3(4) . . . . ?
C12 C11 C16 C15 -0.7(4) . . . . ?
N2 C11 C16 C15 -179.8(2) . . . . ?
C12 C11 C16 C17 178.1(2) . . . . ?
N2 C11 C16 C17 -1.0(3) . . . . ?
C11 C16 C17 C9 -0.5(4) . . . . ?
C15 C16 C17 C9 178.3(2) . . . . ?
C16 C17 C9 C10 0.8(4) . . . . ?
C16 C17 C9 C8 -177.7(2) . . . . ?
O4 C10 C9 C17 179.7(2) . . . . ?
N2 C10 C9 C17 0.3(3) . . . . ?
O4 C10 C9 C8 -1.8(4) . . . . ?
N2 C10 C9 C8 178.8(2) . . . . ?
O2 S1 C5 C6 17.7(3) . . . . ?
O1 S1 C5 C6 149.0(2) . . . . ?
N1 S1 C5 C6 -99.9(2) . . . . ?
O2 S1 C5 C4 -157.4(2) . . . . ?
O1 S1 C5 C4 -26.1(3) . . . . ?
N1 S1 C5 C4 85.1(2) . . . . ?
N2 C11 C12 C13 179.0(2) . . . . ?
C16 C11 C12 C13 -0.1(4) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
S1 C5 C6 C7 -173.6(2) . . . . ?
S1 N1 C8 O3 -0.5(4) . . . . ?
S1 N1 C8 C9 -177.94(19) . . . . ?
C17 C9 C8 O3 -8.5(4) . . . . ?
C10 C9 C8 O3 173.0(3) . . . . ?
C17 C9 C8 N1 169.0(2) . . . . ?
C10 C9 C8 N1 -9.5(4) . . . . ?
C6 C5 C4 C3 -1.5(4) . . . . ?
S1 C5 C4 C3 173.5(2) . . . . ?
C11 C16 C15 C14 0.9(4) . . . . ?
C17 C16 C15 C14 -177.8(3) . . . . ?
C16 C15 C14 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C15 C14 C13 C12 -0.5(5) . . . . ?
C3 C2 C7 C6 -2.3(4) . . . . ?
C1 C2 C7 C6 175.5(3) . . . . ?
C5 C6 C7 C2 0.6(4) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C7 C2 C3 C4 2.2(4) . . . . ?
C1 C2 C3 C4 -175.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.86 1.88 2.610(3) 141.3 .
N1 H1 O4 0.86 1.88 2.610(3) 141.3 .
N1 H1 O4 0.86 1.88 2.610(3) 141.3 .

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044

