# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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 
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data_sf20190405a_0m
_database_code_depnum_ccdc_archive 'CCDC 2046973'
loop_
_audit_author_name
_audit_author_address
'Feng Shi'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2020-11-28 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_audit_creation_date             2019-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H24 N2 O4 S'
_chemical_formula_sum            'C29 H24 N2 O4 S'
_chemical_formula_weight         496.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.3267(18)
_cell_length_b                   8.7156(19)
_cell_length_c                   16.902(4)
_cell_angle_alpha                97.684(3)
_cell_angle_beta                 91.300(2)
_cell_angle_gamma                94.942(2)
_cell_volume                     1210.3(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    182(2)
_cell_measurement_theta_max      27.334
_cell_measurement_theta_min      2.368
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0483 before and 0.0279 after correction.
The Ratio of minimum to maximum transmission is 0.8744.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6813
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.704
_diffrn_ambient_temperature      181.65
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.974
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3803
_reflns_number_total             4826
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.3819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1288
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24),
  C25(H25), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.52065(7) 0.83604(7) 0.39926(3) 0.05356(18) Uani 1 1 d . . . . .
O1 O 0.50498(19) 0.51171(18) 0.34957(8) 0.0580(4) Uani 1 1 d . . . . .
O2 O 0.34187(18) 0.27897(17) 0.08310(9) 0.0556(4) Uani 1 1 d . . . . .
O3 O 0.37365(19) 0.7714(2) 0.42699(9) 0.0722(5) Uani 1 1 d . . . . .
O4 O 0.5411(2) 0.99748(19) 0.39343(10) 0.0707(5) Uani 1 1 d . . . . .
N1 N 0.54338(19) 0.74459(19) 0.30360(9) 0.0434(4) Uani 1 1 d . . . . .
N2 N 0.40508(19) 0.35405(18) 0.21350(9) 0.0424(4) Uani 1 1 d . . . . .
H2 H 0.3949 0.3277 0.2617 0.051 Uiso 1 1 calc R . . . .
C1 C 0.5159(2) 0.5840(2) 0.29355(11) 0.0412(4) Uani 1 1 d . . . . .
C2 C 0.4959(2) 0.5031(2) 0.20677(10) 0.0364(4) Uani 1 1 d . . . . .
C3 C 0.3986(2) 0.6064(2) 0.16105(11) 0.0399(4) Uani 1 1 d . . . . .
H3A H 0.3787 0.5579 0.1049 0.048 Uiso 1 1 calc R . . . .
H3B H 0.2932 0.6195 0.1858 0.048 Uiso 1 1 calc R . . . .
C4 C 0.4937(2) 0.7614(2) 0.16387(11) 0.0392(4) Uani 1 1 d . . . . .
C5 C 0.5186(3) 0.8340(2) 0.09667(13) 0.0502(5) Uani 1 1 d . . . . .
H5 H 0.4697 0.7879 0.0468 0.060 Uiso 1 1 calc R . . . .
C6 C 0.6134(3) 0.9723(3) 0.10124(15) 0.0593(6) Uani 1 1 d . . . . .
H6 H 0.6270 1.0232 0.0552 0.071 Uiso 1 1 calc R . . . .
C7 C 0.6882(3) 1.0365(3) 0.17240(16) 0.0610(6) Uani 1 1 d . . . . .
H7 H 0.7543 1.1317 0.1752 0.073 Uiso 1 1 calc R . . . .
C8 C 0.6692(3) 0.9653(2) 0.23997(14) 0.0541(5) Uani 1 1 d . . . . .
H8 H 0.7238 1.0093 0.2888 0.065 Uiso 1 1 calc R . . . .
C9 C 0.5691(2) 0.8283(2) 0.23576(12) 0.0407(4) Uani 1 1 d . . . . .
C10 C 0.6626(2) 0.4774(2) 0.17300(11) 0.0372(4) Uani 1 1 d . . . . .
C11 C 0.6850(2) 0.4622(3) 0.09253(12) 0.0529(5) Uani 1 1 d . . . . .
H11 H 0.5982 0.4754 0.0573 0.063 Uiso 1 1 calc R . . . .
C12 C 0.8324(3) 0.4279(3) 0.06151(15) 0.0674(7) Uani 1 1 d . . . . .
H12 H 0.8464 0.4200 0.0055 0.081 Uiso 1 1 calc R . . . .
C13 C 0.9571(3) 0.4053(3) 0.11072(17) 0.0635(6) Uani 1 1 d . . . . .
H13 H 1.0566 0.3774 0.0893 0.076 Uiso 1 1 calc R . . . .
C14 C 0.9376(3) 0.4231(3) 0.19160(16) 0.0631(6) Uani 1 1 d . . . . .
H14 H 1.0248 0.4100 0.2266 0.076 Uiso 1 1 calc R . . . .
C15 C 0.7903(2) 0.4603(3) 0.22255(13) 0.0516(5) Uani 1 1 d . . . . .
H15 H 0.7782 0.4740 0.2787 0.062 Uiso 1 1 calc R . . . .
C16 C 0.3358(2) 0.2539(2) 0.15216(12) 0.0415(4) Uani 1 1 d . . . . .
C17 C 0.2434(2) 0.1108(2) 0.17450(14) 0.0476(5) Uani 1 1 d . . . . .
C18 C 0.1471(3) 0.0200(3) 0.11418(17) 0.0654(7) Uani 1 1 d . . . . .
H18 H 0.1448 0.0478 0.0617 0.078 Uiso 1 1 calc R . . . .
C19 C 0.0550(3) -0.1105(3) 0.1311(2) 0.0862(10) Uani 1 1 d . . . . .
H19 H -0.0105 -0.1723 0.0900 0.103 Uiso 1 1 calc R . . . .
C20 C 0.0573(3) -0.1514(3) 0.2063(3) 0.0907(11) Uani 1 1 d . . . . .
H20 H -0.0083 -0.2401 0.2175 0.109 Uiso 1 1 calc R . . . .
C21 C 0.1536(3) -0.0652(3) 0.2655(2) 0.0823(9) Uani 1 1 d . . . . .
H21 H 0.1567 -0.0955 0.3174 0.099 Uiso 1 1 calc R . . . .
C22 C 0.2472(3) 0.0668(3) 0.24989(16) 0.0616(6) Uani 1 1 d . . . . .
H22 H 0.3137 0.1266 0.2912 0.074 Uiso 1 1 calc R . . . .
C23 C 0.6855(2) 0.7829(3) 0.45273(12) 0.0491(5) Uani 1 1 d . . . . .
C24 C 0.6611(3) 0.6968(3) 0.51410(14) 0.0646(6) Uani 1 1 d . . . . .
H24 H 0.5551 0.6612 0.5268 0.078 Uiso 1 1 calc R . . . .
C25 C 0.7925(3) 0.6627(3) 0.55703(14) 0.0691(7) Uani 1 1 d . . . . .
H25 H 0.7760 0.6033 0.5998 0.083 Uiso 1 1 calc R . . . .
C26 C 0.9482(3) 0.7128(3) 0.53950(14) 0.0604(6) Uani 1 1 d . . . . .
C27 C 0.9691(3) 0.7962(3) 0.47664(16) 0.0724(7) Uani 1 1 d . . . . .
H27 H 1.0752 0.8299 0.4629 0.087 Uiso 1 1 calc R . . . .
C28 C 0.8387(3) 0.8320(3) 0.43307(16) 0.0690(7) Uani 1 1 d . . . . .
H28 H 0.8548 0.8903 0.3898 0.083 Uiso 1 1 calc R . . . .
C29 C 1.0912(4) 0.6775(4) 0.58766(18) 0.0860(9) Uani 1 1 d . . . . .
H29A H 1.0907 0.7349 0.6416 0.129 Uiso 1 1 calc GR . . . .
H29B H 1.1907 0.7090 0.5619 0.129 Uiso 1 1 calc GR . . . .
H29C H 1.0853 0.5658 0.5908 0.129 Uiso 1 1 calc GR . . . .


_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 O3 1.4190(17) . ?
S1 O4 1.4195(18) . ?
S1 N1 1.7264(16) . ?
S1 C23 1.755(2) . ?
O1 C1 1.206(2) . ?
O2 C16 1.217(2) . ?
N1 C1 1.386(2) . ?
N1 C9 1.450(3) . ?
N2 H2 0.8800 . ?
N2 C2 1.465(2) . ?
N2 C16 1.347(2) . ?
C1 C2 1.539(2) . ?
C2 C3 1.532(3) . ?
C2 C10 1.535(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.500(3) . ?
C4 C5 1.384(3) . ?
C4 C9 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.369(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C10 C11 1.367(3) . ?
C10 C15 1.370(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.359(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.370(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.505(3) . ?
C17 C18 1.395(3) . ?
C17 C22 1.379(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.366(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.366(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.368(3) . ?
C23 C28 1.373(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(3) . ?
C26 C27 1.372(4) . ?
C26 C29 1.503(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.379(4) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 119.47(12) . . ?
O3 S1 N1 107.43(9) . . ?
O3 S1 C23 110.44(11) . . ?
O4 S1 N1 105.16(9) . . ?
O4 S1 C23 109.80(10) . . ?
N1 S1 C23 103.12(9) . . ?
C1 N1 S1 115.39(13) . . ?
C1 N1 C9 121.14(15) . . ?
C9 N1 S1 123.03(13) . . ?
C2 N2 H2 117.2 . . ?
C16 N2 H2 117.2 . . ?
C16 N2 C2 125.58(16) . . ?
O1 C1 N1 122.00(17) . . ?
O1 C1 C2 121.78(17) . . ?
N1 C1 C2 116.20(16) . . ?
N2 C2 C1 103.91(14) . . ?
N2 C2 C3 111.89(15) . . ?
N2 C2 C10 110.62(15) . . ?
C3 C2 C1 106.54(15) . . ?
C3 C2 C10 113.76(15) . . ?
C10 C2 C1 109.55(14) . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 C2 108.26(15) . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C5 C4 C3 122.65(18) . . ?
C5 C4 C9 118.92(18) . . ?
C9 C4 C3 118.26(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C4 C9 N1 116.63(16) . . ?
C4 C9 C8 120.48(19) . . ?
C8 C9 N1 122.83(18) . . ?
C11 C10 C2 120.92(16) . . ?
C11 C10 C15 118.34(18) . . ?
C15 C10 C2 120.63(17) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(2) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.8(2) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O2 C16 N2 122.65(18) . . ?
O2 C16 C17 121.57(18) . . ?
N2 C16 C17 115.73(18) . . ?
C18 C17 C16 116.6(2) . . ?
C22 C17 C16 124.21(19) . . ?
C22 C17 C18 119.2(2) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.1(3) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 S1 120.37(17) . . ?
C24 C23 C28 120.7(2) . . ?
C28 C23 S1 118.89(18) . . ?
C23 C24 H24 120.5 . . ?
C23 C24 C25 119.0(2) . . ?
C25 C24 H24 120.5 . . ?
C24 C25 H25 119.2 . . ?
C24 C25 C26 121.7(2) . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C29 121.4(2) . . ?
C27 C26 C25 118.1(2) . . ?
C27 C26 C29 120.6(2) . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C28 121.1(2) . . ?
C28 C27 H27 119.5 . . ?
C23 C28 C27 119.5(2) . . ?
C23 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
