# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_180723b_0m
_database_code_depnum_ccdc_archive 'CCDC 1918352'
loop_
_audit_author_name
_audit_author_address
'Yanfei Liu'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-05-24 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N O8 S'
_chemical_formula_weight         473.48

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.6514(3)
_cell_length_b                   11.6340(4)
_cell_length_c                   13.3270(5)
_cell_angle_alpha                76.022(2)
_cell_angle_beta                 79.269(2)
_cell_angle_gamma                86.003(2)
_cell_volume                     1130.68(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9297
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.193
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45379
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.200
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5193
_reflns_number_gt                4084
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.2300P] 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         5193
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.078
_refine_ls_shift/su_mean         0.001

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 0.0105(4) 0.7426(3) 0.9931(2) 0.0958(9) Uani 1 1 d . . . . .
H1A H 0.006330 0.813862 1.017916 0.144 Uiso 1 1 calc R U . . .
H1B H -0.013665 0.676026 1.051937 0.144 Uiso 1 1 calc R U . . .
H1C H -0.077185 0.748283 0.949043 0.144 Uiso 1 1 calc R U . . .
C2 C 0.1929(3) 0.7265(2) 0.93099(16) 0.0638(5) Uani 1 1 d . . . . .
C3 C 0.2834(4) 0.8199(2) 0.86191(19) 0.0751(7) Uani 1 1 d . . . . .
H3 H 0.230685 0.895348 0.853259 0.090 Uiso 1 1 calc R U . . .
C4 C 0.4497(3) 0.80500(19) 0.80525(17) 0.0658(6) Uani 1 1 d . . . . .
H4 H 0.507735 0.869023 0.757890 0.079 Uiso 1 1 calc R U . . .
C5 C 0.5286(3) 0.69367(16) 0.81994(13) 0.0488(4) Uani 1 1 d . . . . .
C6 C 0.4406(3) 0.59743(18) 0.88903(16) 0.0599(5) Uani 1 1 d . . . . .
H6 H 0.494014 0.522196 0.898588 0.072 Uiso 1 1 calc R U . . .
C7 C 0.2732(3) 0.6152(2) 0.94309(16) 0.0663(5) Uani 1 1 d . . . . .
H7 H 0.213019 0.550991 0.988719 0.080 Uiso 1 1 calc R U . . .
C8 C 0.7388(3) 0.46081(16) 0.70115(15) 0.0505(4) Uani 1 1 d . . . . .
C9 C 0.7934(2) 0.40058(14) 0.61382(14) 0.0459(4) Uani 1 1 d . . . . .
H9A H 0.728470 0.327644 0.631324 0.055 Uiso 1 1 calc R U . . .
H9B H 0.918594 0.378700 0.610693 0.055 Uiso 1 1 calc R U . . .
C10 C 0.76758(19) 0.46680(13) 0.50642(13) 0.0393(3) Uani 1 1 d . . . . .
C11 C 0.8030(2) 0.40795(15) 0.42517(16) 0.0497(4) Uani 1 1 d . . . . .
H11 H 0.841801 0.329065 0.438512 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7810(3) 0.46560(17) 0.32591(16) 0.0543(4) Uani 1 1 d . . . . .
H12 H 0.802680 0.425331 0.272263 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7263(2) 0.58397(16) 0.30475(14) 0.0477(4) Uani 1 1 d . . . . .
H13 H 0.714055 0.622295 0.236505 0.057 Uiso 1 1 calc R U . . .
C14 C 0.68976(19) 0.64622(14) 0.38277(12) 0.0374(3) Uani 1 1 d . . . . .
C15 C 0.70813(18) 0.58531(13) 0.48621(12) 0.0350(3) Uani 1 1 d . . . . .
C16 C 0.66589(19) 0.64531(13) 0.57458(12) 0.0367(3) Uani 1 1 d . . . . .
C17 C 0.6375(2) 0.77691(14) 0.35698(12) 0.0391(3) Uani 1 1 d . . . . .
H17 H 0.523849 0.787531 0.402226 0.047 Uiso 1 1 calc R U . . .
C18 C 0.7740(2) 0.85359(15) 0.37887(14) 0.0449(4) Uani 1 1 d . . . . .
C19 C 0.8137(4) 1.04972(18) 0.3954(2) 0.0801(8) Uani 1 1 d . . . . .
H19A H 0.792468 1.128841 0.354492 0.096 Uiso 1 1 calc R U . . .
H19B H 0.939821 1.030546 0.380016 0.096 Uiso 1 1 calc R U . . .
C20 C 0.7605(4) 1.0461(2) 0.5082(3) 0.0853(8) Uani 1 1 d . . . . .
H20A H 0.635062 1.063142 0.523410 0.128 Uiso 1 1 calc R U . . .
H20B H 0.824709 1.104082 0.526092 0.128 Uiso 1 1 calc R U . . .
H20C H 0.786897 0.968706 0.548477 0.128 Uiso 1 1 calc R U . . .
C21 C 0.6133(2) 0.82586(15) 0.24315(13) 0.0458(4) Uani 1 1 d . . . . .
C22 C 0.3981(4) 0.8856(3) 0.13286(19) 0.0916(9) Uani 1 1 d . . . . .
H22A H 0.482339 0.944953 0.091628 0.110 Uiso 1 1 calc R U . . .
H22B H 0.403376 0.821903 0.096921 0.110 Uiso 1 1 calc R U . . .
C23 C 0.2209(5) 0.9374(4) 0.1445(3) 0.1296(14) Uani 1 1 d . . . . .
H23A H 0.137013 0.876517 0.179184 0.194 Uiso 1 1 calc R U . . .
H23B H 0.193587 0.974565 0.076418 0.194 Uiso 1 1 calc R U . . .
H23C H 0.214069 0.995448 0.185498 0.194 Uiso 1 1 calc R U . . .
N1 N 0.72631(18) 0.58703(12) 0.66970(11) 0.0420(3) Uani 1 1 d . . . . .
O1 O 0.8156(2) 0.78076(13) 0.69453(12) 0.0680(4) Uani 1 1 d . . . . .
O2 O 0.8449(2) 0.59945(16) 0.82913(12) 0.0721(4) Uani 1 1 d . . . . .
O3 O 0.7073(3) 0.40881(14) 0.79135(12) 0.0866(6) Uani 1 1 d . . . . .
O4 O 0.58546(17) 0.73851(10) 0.57102(9) 0.0493(3) Uani 1 1 d . . . . .
O5 O 0.91403(17) 0.81907(12) 0.40273(13) 0.0592(4) Uani 1 1 d . . . . .
O6 O 0.7110(2) 0.96416(11) 0.36675(13) 0.0641(4) Uani 1 1 d . . . . .
O7 O 0.7317(2) 0.85302(18) 0.17090(12) 0.0810(5) Uani 1 1 d . . . . .
O8 O 0.44259(19) 0.83994(15) 0.23717(11) 0.0664(4) Uani 1 1 d . . . . .
S1 S 0.74515(6) 0.67201(4) 0.75645(3) 0.05100(16) 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 1.509(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.376(3) . ?
C2 C7 1.380(3) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 S1 1.746(2) . ?
C6 C7 1.376(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O3 1.196(2) . ?
C8 N1 1.428(2) . ?
C8 C9 1.481(3) . ?
C9 C10 1.494(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.392(2) . ?
C10 C15 1.400(2) . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.417(2) . ?
C14 C17 1.518(2) . ?
C15 C16 1.484(2) . ?
C16 O4 1.2040(19) . ?
C16 N1 1.428(2) . ?
C17 C21 1.527(2) . ?
C17 C18 1.530(2) . ?
C17 H17 0.9800 . ?
C18 O5 1.189(2) . ?
C18 O6 1.325(2) . ?
C19 O6 1.470(2) . ?
C19 C20 1.473(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O7 1.190(2) . ?
C21 O8 1.320(2) . ?
C22 C23 1.441(5) . ?
C22 O8 1.458(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 S1 1.7231(15) . ?
O1 S1 1.4134(15) . ?
O2 S1 1.4227(16) . ?

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 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 . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C1 122.0(2) . . ?
C7 C2 C1 119.7(2) . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 120.70(19) . . ?
C4 C5 S1 120.49(16) . . ?
C6 C5 S1 118.75(15) . . ?
C7 C6 C5 118.93(19) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.4(2) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
O3 C8 N1 121.99(18) . . ?
O3 C8 C9 123.19(17) . . ?
N1 C8 C9 114.82(14) . . ?
C8 C9 C10 117.84(14) . . ?
C8 C9 H9A 107.8 . . ?
C10 C9 H9A 107.8 . . ?
C8 C9 H9B 107.8 . . ?
C10 C9 H9B 107.8 . . ?
H9A C9 H9B 107.2 . . ?
C11 C10 C15 119.71(15) . . ?
C11 C10 C9 118.60(15) . . ?
C15 C10 C9 121.68(14) . . ?
C12 C11 C10 120.28(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.32(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 121.53(17) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 118.01(15) . . ?
C13 C14 C17 120.59(15) . . ?
C15 C14 C17 121.36(13) . . ?
C10 C15 C14 120.10(14) . . ?
C10 C15 C16 118.85(14) . . ?
C14 C15 C16 121.05(13) . . ?
O4 C16 N1 118.68(14) . . ?
O4 C16 C15 124.57(14) . . ?
N1 C16 C15 116.75(13) . . ?
C14 C17 C21 114.09(13) . . ?
C14 C17 C18 111.95(13) . . ?
C21 C17 C18 107.16(13) . . ?
C14 C17 H17 107.8 . . ?
C21 C17 H17 107.8 . . ?
C18 C17 H17 107.8 . . ?
O5 C18 O6 125.79(16) . . ?
O5 C18 C17 125.28(15) . . ?
O6 C18 C17 108.94(14) . . ?
O6 C19 C20 109.7(2) . . ?
O6 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
O6 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C21 O8 124.82(17) . . ?
O7 C21 C17 124.69(17) . . ?
O8 C21 C17 110.39(14) . . ?
C23 C22 O8 108.3(3) . . ?
C23 C22 H22A 110.0 . . ?
O8 C22 H22A 110.0 . . ?
C23 C22 H22B 110.0 . . ?
O8 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 N1 C8 121.30(14) . . ?
C16 N1 S1 117.44(11) . . ?
C8 N1 S1 120.26(12) . . ?
C18 O6 C19 117.47(16) . . ?
C21 O8 C22 116.83(17) . . ?
O1 S1 O2 119.03(10) . . ?
O1 S1 N1 106.08(8) . . ?
O2 S1 N1 104.78(9) . . ?
O1 S1 C5 110.45(10) . . ?
O2 S1 C5 109.75(9) . . ?
N1 S1 C5 105.72(8) . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.051

