# 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_lsc-20230706
_database_code_depnum_ccdc_archive 'CCDC 2351202'
loop_
_audit_author_name
_audit_author_address
'Hong-Shuang Li'
;Shandong First Medical University
China
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O4 S'
_chemical_formula_sum            'C23 H21 N O4 S'
_chemical_formula_weight         407.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
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                   18.1956(5)
_cell_length_b                   12.5801(5)
_cell_length_c                   8.9178(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.606(2)
_cell_angle_gamma                90
_cell_volume                     2031.54(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6447
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.9690
_cell_measurement_theta_min      2.4160
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.789
_exptl_absorpt_coefficient_mu    1.662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            18638
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         2.440
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     68.00 178.00   0.50    1.30    --  108.57 133.00 122.00  220
  2  ω     68.00 121.00   0.50    0.15    --   49.86 133.00 122.00  106
  3  ω    -71.00 -32.00   0.50    1.30    -- -105.45  61.00 150.00   78
  4  ω   -102.00 -19.00   0.50    0.15    --  -46.74 137.00 -59.00  166
  5  ω   -121.00 -32.00   0.50    1.30    -- -105.45 137.00 -59.00  178
  6  ω     26.00 122.00   0.50    0.15    --   49.86  77.00  30.00  192
  7  ω     74.00 120.00   0.50    0.15    --   49.86 125.00  60.00   92
  8  ω     94.00 178.00   0.50    1.30    --  108.57  45.00 120.00  168
  9  ω    -25.00  26.00   0.50    0.15    --   49.86 -19.00 -90.00  102
 10  ω     36.00  71.00   0.50    1.30    --  108.57 -61.00-180.00   70
 11  ω     37.00  70.00   0.50    1.30    --  108.57 -61.00-120.00   66
 12  ω     36.00  71.00   0.50    1.30    --  108.57 -61.00 -90.00   70
 13  ω     20.00 105.00   0.50    0.15    --   49.86-137.00-122.00  170
 14  ω     36.00 120.00   0.50    1.30    --  108.57-137.00-122.00  168
 15  ω     53.00 111.00   0.50    1.30    --  108.57-125.00   0.00  116
 16  ω     36.00 105.00   0.50    1.30    --  108.57 -95.00  30.00  138
 17  ω     42.00 103.00   0.50    1.30    --  108.57 -95.00  60.00  122
 18  ω     36.00 105.00   0.50    1.30    --  108.57 -95.00  90.00  138
 19  ω     17.00 102.00   0.50    0.15    --   49.86-133.00  54.00  170
 20  ω   -118.00 -68.00   0.50    0.15    --  -46.74-133.00  54.00  100
 21  ω   -176.00 -68.00   0.50    1.30    -- -105.45-133.00  54.00  216
 22  ω   -177.00 -88.00   0.50    1.30    -- -105.45 -15.00 -60.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0829847000
_diffrn_orient_matrix_UB_12      -0.0005821000
_diffrn_orient_matrix_UB_13      -0.0544173000
_diffrn_orient_matrix_UB_21      0.0002992000
_diffrn_orient_matrix_UB_22      -0.1224479000
_diffrn_orient_matrix_UB_23      0.0032109000
_diffrn_orient_matrix_UB_31      -0.0186746000
_diffrn_orient_matrix_UB_32      0.0021506000
_diffrn_orient_matrix_UB_33      0.1648124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2478
_reflns_number_total             3623
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²+0.0410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C19(H19), C7(H7), C10(H10), C11(H11), C2(H2), C6(H6),
 C3(H3), C20(H20), C22(H22), C21(H21)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.19468(4) 0.55395(6) 0.79484(6) 0.0701(3) Uani 1 1 d . . . . .
O3 O 0.39971(11) 0.80093(15) 0.6804(2) 0.0715(5) Uani 1 1 d . . . . .
N1 N 0.25821(10) 0.53728(17) 0.67698(19) 0.0568(5) Uani 1 1 d . . . . .
O2 O 0.23078(13) 0.6078(2) 0.92189(18) 0.0882(7) Uani 1 1 d . . . . .
O1 O 0.16086(13) 0.45244(19) 0.8120(2) 0.0955(7) Uani 1 1 d . . . . .
O4 O 0.49775(17) 0.9177(2) 0.8272(3) 0.1088(8) Uani 1 1 d . . . . .
H4 H 0.461088 0.905122 0.768951 0.163 Uiso 1 1 calc R U . . .
C15 C 0.30542(12) 0.63282(19) 0.6535(2) 0.0530(5) Uani 1 1 d . . . . .
H15 H 0.280136 0.697350 0.682362 0.064 Uiso 1 1 calc R U . . .
C16 C 0.37862(13) 0.6223(2) 0.7483(2) 0.0566(6) Uani 1 1 d . . . . .
H16A H 0.369565 0.603897 0.850573 0.068 Uiso 1 1 calc R U . . .
H16B H 0.406471 0.564622 0.708919 0.068 Uiso 1 1 calc R U . . .
C8 C 0.23945(12) 0.4865(2) 0.5339(2) 0.0569(6) Uani 1 1 d . . . . .
C17 C 0.42406(13) 0.7221(2) 0.7514(2) 0.0569(6) Uani 1 1 d . . . . .
C13 C 0.26924(13) 0.5422(2) 0.4208(2) 0.0598(6) Uani 1 1 d . . . . .
C18 C 0.49452(14) 0.7263(2) 0.8468(2) 0.0628(7) Uani 1 1 d . . . . .
C1 C 0.12795(14) 0.6394(2) 0.7051(3) 0.0669(7) Uani 1 1 d . . . . .
C14 C 0.31302(15) 0.6348(2) 0.4836(2) 0.0659(7) Uani 1 1 d . . . . .
H14A H 0.293596 0.700599 0.439030 0.079 Uiso 1 1 calc R U . . .
H14B H 0.364377 0.627944 0.464418 0.079 Uiso 1 1 calc R U . . .
C9 C 0.20044(16) 0.3930(2) 0.5053(3) 0.0742(7) Uani 1 1 d . . . . .
H9 H 0.181632 0.354973 0.582444 0.089 Uiso 1 1 calc R U . . .
C12 C 0.25848(16) 0.5051(3) 0.2744(3) 0.0753(8) Uani 1 1 d . . . . .
H12 H 0.278246 0.541801 0.197163 0.090 Uiso 1 1 calc R U . . .
C19 C 0.52815(16) 0.6352(3) 0.9074(3) 0.0795(8) Uani 1 1 d . . . . .
H19 H 0.507131 0.569100 0.884254 0.095 Uiso 1 1 calc R U . . .
C4 C 0.02544(15) 0.7745(3) 0.5506(3) 0.0813(9) Uani 1 1 d . . . . .
C7 C 0.13148(16) 0.7467(3) 0.7289(3) 0.0797(8) Uani 1 1 d . . . . .
H7 H 0.168016 0.774818 0.797762 0.096 Uiso 1 1 calc R U . . .
C23 C 0.52673(19) 0.8255(3) 0.8835(3) 0.0842(9) Uani 1 1 d . . . . .
C10 C 0.19058(18) 0.3585(3) 0.3577(4) 0.0882(9) Uani 1 1 d . . . . .
H10 H 0.164357 0.296137 0.335091 0.106 Uiso 1 1 calc R U . . .
C11 C 0.21855(19) 0.4140(3) 0.2436(3) 0.0902(10) Uani 1 1 d . . . . .
H11 H 0.210349 0.389712 0.144948 0.108 Uiso 1 1 calc R U . . .
C2 C 0.07309(17) 0.5993(3) 0.6029(4) 0.0945(10) Uani 1 1 d . . . . .
H2 H 0.069789 0.526500 0.585197 0.113 Uiso 1 1 calc R U . . .
C6 C 0.08079(18) 0.8137(3) 0.6507(4) 0.0878(9) Uani 1 1 d . . . . .
H6 H 0.084410 0.886621 0.666417 0.105 Uiso 1 1 calc R U . . .
C3 C 0.02289(18) 0.6681(3) 0.5268(5) 0.1004(11) Uani 1 1 d . . . . .
H3 H -0.013593 0.640459 0.457385 0.120 Uiso 1 1 calc R U . . .
C20 C 0.5930(2) 0.6419(4) 1.0024(4) 0.1105(13) Uani 1 1 d . . . . .
H20 H 0.616386 0.580573 1.040498 0.133 Uiso 1 1 calc R U . . .
C5 C -0.0299(2) 0.8471(4) 0.4653(5) 0.1108(13) Uani 1 1 d . . . . .
H5A H -0.059319 0.881420 0.534897 0.166 Uiso 1 1 calc R U . . .
H5B H -0.061363 0.806258 0.394335 0.166 Uiso 1 1 calc R U . . .
H5C H -0.004330 0.899880 0.412606 0.166 Uiso 1 1 calc R U . . .
C22 C 0.5906(3) 0.8294(4) 0.9828(5) 0.1219(16) Uani 1 1 d . . . . .
H22 H 0.611590 0.894813 1.010119 0.146 Uiso 1 1 calc R U . . .
C21 C 0.6222(2) 0.7399(4) 1.0396(5) 0.1252(17) Uani 1 1 d . . . . .
H21 H 0.664902 0.744450 1.105679 0.150 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 N1 1.6500(18) . ?
S1 O2 1.425(2) . ?
S1 O1 1.432(2) . ?
S1 C1 1.755(3) . ?
O3 C17 1.235(3) . ?
N1 C15 1.504(3) . ?
N1 C8 1.438(3) . ?
O4 H4 0.8200 . ?
O4 C23 1.351(4) . ?
C15 H15 0.9800 . ?
C15 C16 1.512(3) . ?
C15 C14 1.535(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.503(3) . ?
C8 C13 1.382(3) . ?
C8 C9 1.385(4) . ?
C17 C18 1.469(4) . ?
C13 C14 1.489(4) . ?
C13 C12 1.382(4) . ?
C18 C19 1.384(4) . ?
C18 C23 1.404(4) . ?
C1 C7 1.367(4) . ?
C1 C2 1.380(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.381(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.370(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(5) . ?
C4 C6 1.370(5) . ?
C4 C3 1.355(5) . ?
C4 C5 1.509(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.386(5) . ?
C23 C22 1.391(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(5) . ?
C11 H11 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.387(5) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.370(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C21 1.340(7) . ?
C21 H21 0.9300 . ?

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
N1 S1 C1 106.51(10) . . ?
O2 S1 N1 105.65(12) . . ?
O2 S1 O1 120.60(13) . . ?
O2 S1 C1 108.41(14) . . ?
O1 S1 N1 106.84(12) . . ?
O1 S1 C1 108.01(14) . . ?
C15 N1 S1 115.63(16) . . ?
C8 N1 S1 120.09(16) . . ?
C8 N1 C15 108.69(16) . . ?
C23 O4 H4 109.5 . . ?
N1 C15 H15 109.6 . . ?
N1 C15 C16 109.61(18) . . ?
N1 C15 C14 104.97(19) . . ?
C16 C15 H15 109.6 . . ?
C16 C15 C14 113.23(19) . . ?
C14 C15 H15 109.6 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 112.9(2) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C13 C8 N1 110.3(2) . . ?
C13 C8 C9 121.8(2) . . ?
C9 C8 N1 127.9(2) . . ?
O3 C17 C16 119.5(2) . . ?
O3 C17 C18 121.2(2) . . ?
C18 C17 C16 119.2(2) . . ?
C8 C13 C14 110.8(2) . . ?
C8 C13 C12 119.3(3) . . ?
C12 C13 C14 129.8(2) . . ?
C19 C18 C17 121.6(2) . . ?
C19 C18 C23 119.1(3) . . ?
C23 C18 C17 119.2(3) . . ?
C7 C1 S1 120.9(2) . . ?
C7 C1 C2 118.9(3) . . ?
C2 C1 S1 120.1(3) . . ?
C15 C14 H14A 110.7 . . ?
C15 C14 H14B 110.7 . . ?
C13 C14 C15 105.20(19) . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C8 C9 H9 121.3 . . ?
C10 C9 C8 117.3(3) . . ?
C10 C9 H9 121.3 . . ?
C13 C12 H12 120.2 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C6 C4 C5 121.5(4) . . ?
C3 C4 C6 118.0(3) . . ?
C3 C4 C5 120.5(3) . . ?
C1 C7 H7 119.9 . . ?
C1 C7 C6 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
O4 C23 C18 122.6(3) . . ?
O4 C23 C22 118.5(4) . . ?
C22 C23 C18 118.9(4) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C4 C6 C7 121.3(3) . . ?
C4 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.3(4) . . ?
C21 C20 H20 120.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C23 C22 H22 119.6 . . ?
C21 C22 C23 120.8(4) . . ?
C21 C22 H22 119.6 . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.4(4) . . ?
C22 C21 H21 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C15 C16 99.70(19) . . . . ?
S1 N1 C15 C14 -138.39(17) . . . . ?
S1 N1 C8 C13 135.22(18) . . . . ?
S1 N1 C8 C9 -47.6(3) . . . . ?
S1 C1 C7 C6 176.3(2) . . . . ?
S1 C1 C2 C3 -176.7(3) . . . . ?
O3 C17 C18 C19 -169.5(2) . . . . ?
O3 C17 C18 C23 13.7(3) . . . . ?
N1 S1 C1 C7 -93.7(2) . . . . ?
N1 S1 C1 C2 82.9(3) . . . . ?
N1 C15 C16 C17 -170.47(17) . . . . ?
N1 C15 C14 C13 0.8(3) . . . . ?
N1 C8 C13 C14 1.7(3) . . . . ?
N1 C8 C13 C12 178.9(2) . . . . ?
N1 C8 C9 C10 -178.6(3) . . . . ?
O2 S1 N1 C15 -45.23(19) . . . . ?
O2 S1 N1 C8 -178.77(19) . . . . ?
O2 S1 C1 C7 19.6(2) . . . . ?
O2 S1 C1 C2 -163.8(2) . . . . ?
O1 S1 N1 C15 -174.81(17) . . . . ?
O1 S1 N1 C8 51.7(2) . . . . ?
O1 S1 C1 C7 151.9(2) . . . . ?
O1 S1 C1 C2 -31.6(3) . . . . ?
O4 C23 C22 C21 -178.8(4) . . . . ?
C15 N1 C8 C13 -1.1(3) . . . . ?
C15 N1 C8 C9 176.1(3) . . . . ?
C15 C16 C17 O3 0.0(3) . . . . ?
C15 C16 C17 C18 176.08(19) . . . . ?
C16 C15 C14 C13 120.3(2) . . . . ?
C16 C17 C18 C19 14.5(3) . . . . ?
C16 C17 C18 C23 -162.3(2) . . . . ?
C8 N1 C15 C16 -121.8(2) . . . . ?
C8 N1 C15 C14 0.1(3) . . . . ?
C8 C13 C14 C15 -1.6(3) . . . . ?
C8 C13 C12 C11 0.0(4) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C17 C18 C19 C20 -177.2(3) . . . . ?
C17 C18 C23 O4 -4.0(4) . . . . ?
C17 C18 C23 C22 175.3(3) . . . . ?
C13 C8 C9 C10 -1.7(4) . . . . ?
C13 C12 C11 C10 -1.3(5) . . . . ?
C18 C19 C20 C21 2.1(6) . . . . ?
C18 C23 C22 C21 1.8(6) . . . . ?
C1 S1 N1 C15 69.93(18) . . . . ?
C1 S1 N1 C8 -63.6(2) . . . . ?
C1 C7 C6 C4 1.3(4) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C14 C15 C16 C17 72.7(3) . . . . ?
C14 C13 C12 C11 176.6(3) . . . . ?
C9 C8 C13 C14 -175.7(2) . . . . ?
C9 C8 C13 C12 1.5(4) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C12 C13 C14 C15 -178.4(3) . . . . ?
C19 C18 C23 O4 179.0(3) . . . . ?
C19 C18 C23 C22 -1.6(4) . . . . ?
C19 C20 C21 C22 -1.9(7) . . . . ?
C7 C1 C2 C3 0.0(5) . . . . ?
C23 C18 C19 C20 -0.3(4) . . . . ?
C23 C22 C21 C20 -0.1(7) . . . . ?
C2 C1 C7 C6 -0.3(4) . . . . ?
C6 C4 C3 C2 1.6(5) . . . . ?
C3 C4 C6 C7 -1.9(5) . . . . ?
C5 C4 C6 C7 179.9(3) . . . . ?
C5 C4 C3 C2 179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.695
####################################################################### 
# 
# 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 2351203'
loop_
_audit_author_name
_audit_author_address
'Hong-Shuang Li'
;Shandong First Medical University
China
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;
_audit_creation_date             2024-04-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O3'
_chemical_formula_sum            'C18 H17 N O3'
_chemical_formula_weight         295.32
_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'

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

_cell_length_a                   8.7829(7)
_cell_length_b                   9.1621(10)
_cell_length_c                   9.6636(11)
_cell_angle_alpha                98.556(5)
_cell_angle_beta                 96.030(6)
_cell_angle_gamma                101.052(6)
_cell_volume                     747.53(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1575
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      49.05
_cell_measurement_theta_min      8.15
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1316 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.7915.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13441
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.152
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                2485
_reflns_number_total             3027
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.090
_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)+(0.0656P)²+0.0829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1266
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O1 O 0.65571(12) 0.46036(13) -0.14202(11) 0.0697(3) Uani 1 1 d . . . . .
O2 O 0.86780(11) 0.88351(12) 0.43296(12) 0.0680(3) Uani 1 1 d . . . . .
O3 O 0.79137(11) 1.03458(11) 0.65334(11) 0.0606(3) Uani 1 1 d . . . . .
H3 H 0.849390 1.013951 0.595567 0.091 Uiso 1 1 calc R U . . .
N1 N 0.79174(12) 0.54469(12) 0.07605(11) 0.0437(3) Uani 1 1 d . . . . .
C1 C 0.6513(2) 0.7113(2) -0.04066(19) 0.0709(5) Uani 1 1 d . . . . .
H1A H 0.641220 0.731976 -0.135330 0.106 Uiso 1 1 calc R U . . .
H1B H 0.729350 0.789919 0.018535 0.106 Uiso 1 1 calc R U . . .
H1C H 0.552694 0.707106 -0.005312 0.106 Uiso 1 1 calc R U . . .
C2 C 0.84819(14) 0.41230(14) 0.09165(13) 0.0438(3) Uani 1 1 d . . . . .
C3 C 0.81323(17) 0.27312(16) 0.00378(16) 0.0570(4) Uani 1 1 d . . . . .
H3A H 0.744879 0.255956 -0.080035 0.068 Uiso 1 1 calc R U . . .
C4 C 0.69940(14) 0.56213(16) -0.04047(14) 0.0512(3) Uani 1 1 d . . . . .
C5 C 0.8831(2) 0.16030(18) 0.0445(2) 0.0712(5) Uani 1 1 d . . . . .
H5 H 0.861656 0.066066 -0.013319 0.085 Uiso 1 1 calc R U . . .
C6 C 1.02046(18) 0.3256(2) 0.25499(17) 0.0674(4) Uani 1 1 d . . . . .
H6 H 1.089759 0.342547 0.338197 0.081 Uiso 1 1 calc R U . . .
C7 C 0.95298(15) 0.44004(16) 0.21585(13) 0.0482(3) Uani 1 1 d . . . . .
C8 C 0.97741(15) 0.60205(17) 0.28417(14) 0.0541(4) Uani 1 1 d . . . . .
H8A H 1.078425 0.658692 0.270761 0.065 Uiso 1 1 calc R U . . .
H8B H 0.971055 0.610820 0.384573 0.065 Uiso 1 1 calc R U . . .
C9 C 0.84338(14) 0.65817(14) 0.20801(13) 0.0451(3) Uani 1 1 d . . . . .
H9 H 0.881941 0.758369 0.185516 0.054 Uiso 1 1 calc R U . . .
C10 C 0.70762(14) 0.66125(15) 0.29444(14) 0.0486(3) Uani 1 1 d . . . . .
H10A H 0.614865 0.666135 0.232755 0.058 Uiso 1 1 calc R U . . .
H10B H 0.685566 0.568126 0.332016 0.058 Uiso 1 1 calc R U . . .
C11 C 0.74118(14) 0.79301(14) 0.41488(14) 0.0464(3) Uani 1 1 d . . . . .
C12 C 0.62231(14) 0.81221(14) 0.50802(13) 0.0431(3) Uani 1 1 d . . . . .
C13 C 0.47415(15) 0.71445(16) 0.48373(15) 0.0527(3) Uani 1 1 d . . . . .
H13 H 0.451766 0.633821 0.408714 0.063 Uiso 1 1 calc R U . . .
C14 C 0.36211(17) 0.73609(19) 0.56888(16) 0.0608(4) Uani 1 1 d . . . . .
H14 H 0.264510 0.670703 0.551534 0.073 Uiso 1 1 calc R U . . .
C15 C 0.53774(18) 0.95338(18) 0.70683(15) 0.0589(4) Uani 1 1 d . . . . .
H15 H 0.557727 1.033506 0.782207 0.071 Uiso 1 1 calc R U . . .
C16 C 0.65327(15) 0.93423(14) 0.62194(13) 0.0465(3) Uani 1 1 d . . . . .
C17 C 0.39516(18) 0.8558(2) 0.68079(16) 0.0637(4) Uani 1 1 d . . . . .
H17 H 0.319449 0.870090 0.738940 0.076 Uiso 1 1 calc R U . . .
C18 C 0.9835(2) 0.1845(2) 0.1684(2) 0.0783(5) Uani 1 1 d . . . . .
H18 H 1.027089 0.106128 0.194632 0.094 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
O1 C4 1.2211(17) . ?
O2 C11 1.2317(15) . ?
O3 H3 0.8200 . ?
O3 C16 1.3493(16) . ?
N1 C2 1.4174(16) . ?
N1 C4 1.3648(17) . ?
N1 C9 1.4886(15) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C4 1.506(2) . ?
C2 C3 1.3836(18) . ?
C2 C7 1.3927(18) . ?
C3 H3A 0.9300 . ?
C3 C5 1.383(2) . ?
C5 H5 0.9300 . ?
C5 C18 1.373(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(2) . ?
C6 C18 1.392(3) . ?
C7 C8 1.4972(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.5343(18) . ?
C9 H9 0.9800 . ?
C9 C10 1.5282(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5074(17) . ?
C11 C12 1.4670(18) . ?
C12 C13 1.4061(18) . ?
C12 C16 1.4107(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(2) . ?
C14 H14 0.9300 . ?
C14 C17 1.384(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(2) . ?
C15 C17 1.367(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
C16 O3 H3 109.5 . . ?
C2 N1 C9 109.50(10) . . ?
C4 N1 C2 124.82(11) . . ?
C4 N1 C9 125.64(11) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
C3 C2 N1 129.25(12) . . ?
C3 C2 C7 121.44(13) . . ?
C7 C2 N1 109.30(11) . . ?
C2 C3 H3A 121.0 . . ?
C2 C3 C5 117.93(15) . . ?
C5 C3 H3A 121.0 . . ?
O1 C4 N1 121.55(13) . . ?
O1 C4 C1 120.37(13) . . ?
N1 C4 C1 118.08(13) . . ?
C3 C5 H5 119.3 . . ?
C18 C5 C3 121.40(15) . . ?
C18 C5 H5 119.3 . . ?
C7 C6 H6 120.4 . . ?
C7 C6 C18 119.17(16) . . ?
C18 C6 H6 120.4 . . ?
C2 C7 C8 110.02(11) . . ?
C6 C7 C2 119.66(14) . . ?
C6 C7 C8 130.27(13) . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C7 C8 C9 103.82(10) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
N1 C9 C8 103.65(10) . . ?
N1 C9 H9 110.4 . . ?
N1 C9 C10 109.90(10) . . ?
C8 C9 H9 110.4 . . ?
C10 C9 C8 111.98(11) . . ?
C10 C9 H9 110.4 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 112.84(10) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
O2 C11 C10 119.40(11) . . ?
O2 C11 C12 121.02(11) . . ?
C12 C11 C10 119.58(11) . . ?
C13 C12 C11 121.50(11) . . ?
C13 C12 C16 118.46(12) . . ?
C16 C12 C11 120.00(11) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.06(13) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C17 119.61(14) . . ?
C17 C14 H14 120.2 . . ?
C16 C15 H15 119.6 . . ?
C17 C15 H15 119.6 . . ?
C17 C15 C16 120.78(13) . . ?
O3 C16 C12 122.90(11) . . ?
O3 C16 C15 117.79(12) . . ?
C15 C16 C12 119.31(13) . . ?
C14 C17 H17 119.6 . . ?
C15 C17 C14 120.78(13) . . ?
C15 C17 H17 119.6 . . ?
C5 C18 C6 120.35(15) . . ?
C5 C18 H18 119.8 . . ?
C6 C18 H18 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
