# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_exp_10845
_database_code_depnum_ccdc_archive 'CCDC 2040018'
loop_
_audit_author_name
_audit_author_address
'maozhong miao'
;zhejiang sci tech university
China
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2021-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 N O5 S'
_chemical_formula_weight         461.51

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.5921(4)
_cell_length_b                   9.8807(3)
_cell_length_c                   23.3768(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2215.58(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2522
_cell_measurement_theta_min      3.7930
_cell_measurement_theta_max      70.8740

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.628
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_T_min  0.94218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5570
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.782
_diffrn_reflns_theta_max         67.211
_diffrn_reflns_theta_full        67.211
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.874
_reflns_number_total             3472
_reflns_number_gt                3087
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_max     0.705
_reflns_Friedel_fraction_full    0.706

_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0477P)²+0.2985P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0046(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(16)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.003
_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 0.51296(11) 0.77182(9) 0.41315(4) 0.0449(3) Uani 1 1 d . . . . .
N1 N 0.6165(3) 0.6399(3) 0.43299(13) 0.0376(7) Uani 1 1 d . . . . .
O1 O 0.5278(4) 0.8763(3) 0.45433(12) 0.0619(9) Uani 1 1 d . . . . .
O2 O 0.3799(3) 0.7129(3) 0.40333(13) 0.0555(8) Uani 1 1 d . . . . .
O3 O 0.5912(2) 0.2857(2) 0.40066(10) 0.0363(6) Uani 1 1 d . . . . .
O4 O 0.8086(3) 0.7753(3) 0.43322(12) 0.0537(7) Uani 1 1 d . . . . .
O5 O 0.9111(4) 0.5504(3) 0.15208(13) 0.0680(9) Uani 1 1 d . . . . .
C1 C 0.7543(6) 0.9424(6) 0.1864(2) 0.0728(15) Uani 1 1 d . . . . .
H1A H 0.689964 0.997775 0.165405 0.109 Uiso 1 1 calc R U . . .
H1B H 0.775522 0.862603 0.164687 0.109 Uiso 1 1 calc R U . . .
H1C H 0.838422 0.992387 0.193356 0.109 Uiso 1 1 calc R U . . .
C2 C 0.6899(4) 0.9023(4) 0.24259(17) 0.0508(11) Uani 1 1 d . . . . .
C3 C 0.7144(5) 0.9774(4) 0.2914(2) 0.0593(12) Uani 1 1 d . . . . .
H3 H 0.769033 1.054936 0.288781 0.071 Uiso 1 1 calc R U . . .
C4 C 0.6604(5) 0.9409(4) 0.34374(17) 0.0529(11) Uani 1 1 d . . . . .
H4 H 0.676969 0.993514 0.376026 0.063 Uiso 1 1 calc R U . . .
C5 C 0.5817(4) 0.8254(4) 0.34723(16) 0.0420(9) Uani 1 1 d . . . . .
C6 C 0.5544(4) 0.7475(4) 0.29919(17) 0.0500(10) Uani 1 1 d . . . . .
H6 H 0.500095 0.669789 0.301873 0.060 Uiso 1 1 calc R U . . .
C7 C 0.6094(5) 0.7875(4) 0.24726(18) 0.0553(11) Uani 1 1 d . . . . .
H7 H 0.591722 0.735809 0.214812 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4621(3) 0.3030(3) 0.42614(14) 0.0332(8) Uani 1 1 d . . . . .
C9 C 0.3644(4) 0.2029(4) 0.43238(16) 0.0413(9) Uani 1 1 d . . . . .
H9 H 0.379911 0.115189 0.419421 0.050 Uiso 1 1 calc R U . . .
C10 C 0.2412(4) 0.2396(4) 0.45907(17) 0.0449(9) Uani 1 1 d . . . . .
H10 H 0.171360 0.175420 0.464163 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2205(4) 0.3713(4) 0.47836(16) 0.0420(9) Uani 1 1 d . . . . .
H11 H 0.137169 0.392759 0.496581 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3187(4) 0.4701(4) 0.47136(15) 0.0381(8) Uani 1 1 d . . . . .
H12 H 0.303136 0.557210 0.484980 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4431(4) 0.4374(4) 0.44328(14) 0.0323(7) Uani 1 1 d . . . . .
C14 C 0.5692(4) 0.5036(3) 0.42508(15) 0.0322(8) Uani 1 1 d . . . . .
C15 C 0.7633(4) 0.6623(4) 0.43250(16) 0.0416(9) Uani 1 1 d . . . . .
C16 C 0.8525(4) 0.5373(4) 0.42963(17) 0.0427(9) Uani 1 1 d . . . . .
H16A H 0.855073 0.496035 0.467264 0.051 Uiso 1 1 calc R U . . .
H16B H 0.946980 0.564000 0.419992 0.051 Uiso 1 1 calc R U . . .
C17 C 0.8035(4) 0.4304(4) 0.38610(15) 0.0353(8) Uani 1 1 d . . . . .
C18 C 0.6534(4) 0.4118(3) 0.40157(15) 0.0328(7) Uani 1 1 d . . . . .
C19 C 0.8882(4) 0.2993(4) 0.39572(17) 0.0458(9) Uani 1 1 d . . . . .
H19A H 0.876454 0.269398 0.434503 0.069 Uiso 1 1 calc R U . . .
H19B H 0.985121 0.316727 0.388580 0.069 Uiso 1 1 calc R U . . .
H19C H 0.855717 0.230275 0.370072 0.069 Uiso 1 1 calc R U . . .
C20 C 0.8199(4) 0.4732(4) 0.32325(16) 0.0375(8) Uani 1 1 d . . . . .
C21 C 0.8937(4) 0.5857(4) 0.30612(18) 0.0480(10) Uani 1 1 d . . . . .
H21 H 0.926033 0.646408 0.333480 0.058 Uiso 1 1 calc R U . . .
C22 C 0.9204(4) 0.6099(4) 0.24881(18) 0.0513(11) Uani 1 1 d . . . . .
H22 H 0.970419 0.686486 0.238169 0.062 Uiso 1 1 calc R U . . .
C23 C 0.8739(4) 0.5220(4) 0.20756(18) 0.0481(10) Uani 1 1 d . . . . .
C24 C 0.7937(5) 0.4128(4) 0.22314(18) 0.0533(11) Uani 1 1 d . . . . .
H24 H 0.758677 0.354176 0.195551 0.064 Uiso 1 1 calc R U . . .
C25 C 0.7658(4) 0.3914(4) 0.28078(17) 0.0489(10) Uani 1 1 d . . . . .
H25 H 0.708566 0.319435 0.291120 0.059 Uiso 1 1 calc R U . . .
C26 C 0.9099(6) 0.4450(5) 0.1121(2) 0.0727(15) Uani 1 1 d . . . . .
H26A H 0.955514 0.367152 0.128005 0.109 Uiso 1 1 calc R U . . .
H26B H 0.958082 0.473116 0.078104 0.109 Uiso 1 1 calc R U . . .
H26C H 0.815283 0.422440 0.102704 0.109 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 1.419(3) . ?
S1 O2 1.421(3) . ?
S1 N1 1.703(3) . ?
S1 C5 1.758(4) . ?
N1 C15 1.425(5) . ?
N1 C14 1.434(4) . ?
O3 C18 1.381(4) . ?
O3 C8 1.385(4) . ?
O4 C15 1.198(4) . ?
O5 C23 1.374(5) . ?
O5 C26 1.400(6) . ?
C1 C2 1.504(6) . ?
C2 C7 1.377(6) . ?
C2 C3 1.380(6) . ?
C3 C4 1.378(6) . ?
C4 C5 1.371(5) . ?
C5 C6 1.387(5) . ?
C6 C7 1.381(6) . ?
C8 C9 1.370(5) . ?
C8 C13 1.400(4) . ?
C9 C10 1.384(5) . ?
C10 C11 1.391(5) . ?
C11 C12 1.366(5) . ?
C12 C13 1.400(5) . ?
C13 C14 1.439(5) . ?
C14 C18 1.333(4) . ?
C15 C16 1.504(5) . ?
C16 C17 1.541(5) . ?
C17 C18 1.496(5) . ?
C17 C20 1.537(5) . ?
C17 C19 1.546(5) . ?
C20 C21 1.378(5) . ?
C20 C25 1.381(5) . ?
C21 C22 1.385(6) . ?
C22 C23 1.373(6) . ?
C23 C24 1.374(5) . ?
C24 C25 1.390(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.85(19) . . ?
O1 S1 N1 108.26(18) . . ?
O2 S1 N1 104.74(15) . . ?
O1 S1 C5 109.75(18) . . ?
O2 S1 C5 108.58(19) . . ?
N1 S1 C5 104.52(16) . . ?
C15 N1 C14 117.2(3) . . ?
C15 N1 S1 117.1(2) . . ?
C14 N1 S1 120.0(2) . . ?
C18 O3 C8 105.6(2) . . ?
C23 O5 C26 118.4(4) . . ?
C7 C2 C3 118.2(4) . . ?
C7 C2 C1 121.1(4) . . ?
C3 C2 C1 120.7(4) . . ?
C4 C3 C2 122.0(4) . . ?
C5 C4 C3 118.6(4) . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 S1 120.6(3) . . ?
C6 C5 S1 118.2(3) . . ?
C7 C6 C5 118.7(4) . . ?
C2 C7 C6 121.3(4) . . ?
C9 C8 O3 124.7(3) . . ?
C9 C8 C13 124.5(3) . . ?
O3 C8 C13 110.8(3) . . ?
C8 C9 C10 116.3(3) . . ?
C9 C10 C11 120.9(4) . . ?
C12 C11 C10 122.1(4) . . ?
C11 C12 C13 118.7(3) . . ?
C8 C13 C12 117.6(3) . . ?
C8 C13 C14 103.7(3) . . ?
C12 C13 C14 138.7(3) . . ?
C18 C14 N1 120.0(3) . . ?
C18 C14 C13 108.8(3) . . ?
N1 C14 C13 130.9(3) . . ?
O4 C15 N1 120.2(4) . . ?
O4 C15 C16 124.0(4) . . ?
N1 C15 C16 115.8(3) . . ?
C15 C16 C17 114.7(3) . . ?
C18 C17 C20 111.3(3) . . ?
C18 C17 C16 102.6(3) . . ?
C20 C17 C16 114.3(3) . . ?
C18 C17 C19 111.6(3) . . ?
C20 C17 C19 108.4(3) . . ?
C16 C17 C19 108.5(3) . . ?
C14 C18 O3 111.0(3) . . ?
C14 C18 C17 126.9(3) . . ?
O3 C18 C17 121.5(3) . . ?
C21 C20 C25 117.2(4) . . ?
C21 C20 C17 123.5(4) . . ?
C25 C20 C17 119.2(3) . . ?
C20 C21 C22 121.0(4) . . ?
C23 C22 C21 120.7(4) . . ?
C22 C23 C24 119.5(4) . . ?
C22 C23 O5 116.7(4) . . ?
C24 C23 O5 123.8(4) . . ?
C23 C24 C25 119.0(4) . . ?
C20 C25 C24 122.3(4) . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039



