# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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. 
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data_181206_xsh_5_82_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1883882'
loop_
_audit_author_name
_audit_author_address
'Sunliang Cui'
;Zhejiang University
China
;
_audit_update_record             
;
2018-12-08 deposited with the CCDC.	2022-05-27 downloaded from the CCDC.
;
_audit_creation_date             2018-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O6 S'
_chemical_formula_sum            'C21 H22 N2 O6 S'
_chemical_formula_weight         430.46
_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                   8.9610(3)
_cell_length_b                   10.1919(3)
_cell_length_c                   11.3979(3)
_cell_angle_alpha                89.2280(10)
_cell_angle_beta                 84.5900(10)
_cell_angle_gamma                89.6090(10)
_cell_volume                     1036.22(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      35.40
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0794 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.9046.
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    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.226
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33755
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         39.418
_diffrn_reflns_theta_min         2.283
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                7614
_reflns_number_total             12284
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.581
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         12284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.035
_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)+(0.0661P)²+0.2519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1707
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_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 0.46523(3) 0.67547(3) 0.65855(3) 0.03050(8) Uani 1 1 d . . . . .
O1 O 1.01669(13) 0.30177(10) 0.32611(9) 0.0391(2) Uani 1 1 d . . . . .
O2 O 0.80029(13) -0.00828(9) 0.57576(9) 0.0376(2) Uani 1 1 d . . . . .
O3 O 0.95653(9) 0.22512(8) 0.56368(7) 0.02508(15) Uani 1 1 d . . . . .
O4 O 0.59710(12) 0.43746(10) 0.72824(9) 0.0385(2) Uani 1 1 d . . . . .
O5 O 0.34318(11) 0.58586(12) 0.67334(10) 0.0433(3) Uani 1 1 d . . . . .
O6 O 0.44840(13) 0.79220(12) 0.58908(10) 0.0459(3) Uani 1 1 d . . . . .
N1 N 0.89847(11) 0.16773(9) 0.46911(8) 0.02364(16) Uani 1 1 d . . . . .
N2 N 0.61717(11) 0.60157(10) 0.59205(9) 0.02666(18) Uani 1 1 d . . . . .
C1 C 0.94254(14) 0.20653(12) 0.35374(10) 0.0272(2) Uani 1 1 d . . . . .
C2 C 0.87957(16) 0.10560(13) 0.27682(11) 0.0336(3) Uani 1 1 d . . . . .
H2A H 0.960801 0.064877 0.224366 0.040 Uiso 1 1 calc R . . . .
H2B H 0.806359 0.146675 0.227569 0.040 Uiso 1 1 calc R . . . .
C3 C 0.80306(16) 0.00281(12) 0.36015(11) 0.0321(2) Uani 1 1 d . . . . .
H3A H 0.694475 -0.000952 0.350721 0.039 Uiso 1 1 calc R . . . .
H3B H 0.847657 -0.085062 0.344366 0.039 Uiso 1 1 calc R . . . .
C4 C 0.82880(14) 0.04636(11) 0.48196(10) 0.0266(2) Uani 1 1 d . . . . .
C5 C 0.83813(13) 0.29378(11) 0.63871(9) 0.02405(19) Uani 1 1 d . . . . .
H5 H 0.744326 0.240566 0.644141 0.029 Uiso 1 1 calc R . . . .
C6 C 0.80827(13) 0.42635(11) 0.58286(10) 0.02482(19) Uani 1 1 d . . . . .
H6A H 0.893658 0.485561 0.591152 0.030 Uiso 1 1 calc R . . . .
H6B H 0.798480 0.415540 0.497738 0.030 Uiso 1 1 calc R . . . .
C7 C 0.66577(13) 0.48638(11) 0.64170(10) 0.0263(2) Uani 1 1 d . . . . .
C8 C 0.51307(13) 0.72015(12) 0.79795(11) 0.0280(2) Uani 1 1 d . . . . .
C9 C 0.45080(18) 0.65450(16) 0.89708(13) 0.0406(3) Uani 1 1 d . . . . .
H9 H 0.385891 0.582339 0.889845 0.049 Uiso 1 1 calc R . . . .
C10 C 0.4837(2) 0.69473(17) 1.00738(13) 0.0438(3) Uani 1 1 d . . . . .
H10 H 0.440260 0.649971 1.075727 0.053 Uiso 1 1 calc R . . . .
C11 C 0.57857(19) 0.79861(16) 1.01956(13) 0.0404(3) Uani 1 1 d . . . . .
C12 C 0.6410(2) 0.86195(18) 0.91823(15) 0.0529(5) Uani 1 1 d . . . . .
H12 H 0.706995 0.933347 0.925448 0.063 Uiso 1 1 calc R . . . .
C13 C 0.6100(2) 0.82408(15) 0.80702(13) 0.0434(3) Uani 1 1 d . . . . .
H13 H 0.653988 0.868274 0.738555 0.052 Uiso 1 1 calc R . . . .
C14 C 0.6129(3) 0.8421(2) 1.13995(15) 0.0599(5) Uani 1 1 d . . . . .
H14A H 0.573040 0.930884 1.154252 0.090 Uiso 1 1 calc GR . . . .
H14B H 0.721627 0.842173 1.143925 0.090 Uiso 1 1 calc GR . . . .
H14C H 0.566198 0.781692 1.199953 0.090 Uiso 1 1 calc GR . . . .
C15 C 0.89915(14) 0.29453(12) 0.75763(10) 0.0264(2) Uani 1 1 d . . . . .
C16 C 0.85742(19) 0.19369(16) 0.83573(12) 0.0403(3) Uani 1 1 d . . . . .
H16 H 0.790403 0.128411 0.814019 0.048 Uiso 1 1 calc R . . . .
C17 C 0.9121(2) 0.18652(19) 0.94548(14) 0.0504(4) Uani 1 1 d . . . . .
H17 H 0.881752 0.116904 0.998483 0.060 Uiso 1 1 calc R . . . .
C18 C 1.0098(2) 0.27933(19) 0.97792(13) 0.0499(4) Uani 1 1 d . . . . .
H18 H 1.045859 0.275253 1.053639 0.060 Uiso 1 1 calc R . . . .
C19 C 1.0550(2) 0.37844(19) 0.89970(15) 0.0522(4) Uani 1 1 d . . . . .
H19 H 1.124210 0.441971 0.921297 0.063 Uiso 1 1 calc R . . . .
C20 C 1.00084(19) 0.38687(15) 0.78933(13) 0.0408(3) Uani 1 1 d . . . . .
H20 H 1.033261 0.455491 0.735889 0.049 Uiso 1 1 calc R . . . .
C21 C 0.69965(15) 0.66939(13) 0.49101(12) 0.0323(2) Uani 1 1 d . . . . .
H21A H 0.674843 0.629685 0.417513 0.048 Uiso 1 1 calc GR . . . .
H21B H 0.807661 0.661130 0.497200 0.048 Uiso 1 1 calc GR . . . .
H21C H 0.671266 0.762424 0.491173 0.048 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 O5 1.4259(11) . ?
S1 O6 1.4352(12) . ?
S1 N2 1.6740(10) . ?
S1 C8 1.7511(12) . ?
O1 C1 1.2017(16) . ?
O2 C4 1.2053(15) . ?
O3 N1 1.3790(12) . ?
O3 C5 1.4770(13) . ?
O4 C7 1.2152(15) . ?
N1 C1 1.3898(15) . ?
N1 C4 1.3892(15) . ?
N2 C7 1.3819(15) . ?
N2 C21 1.4749(16) . ?
C1 C2 1.5069(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5264(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5020(17) . ?
C5 H5 1.0000 . ?
C5 C6 1.5187(15) . ?
C5 C15 1.5088(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5145(16) . ?
C8 C9 1.3790(19) . ?
C8 C13 1.3852(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(2) . ?
C11 C12 1.388(2) . ?
C11 C14 1.507(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.3807(18) . ?
C15 C20 1.3890(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.376(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(2) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
O5 S1 O6 118.33(7) . . ?
O5 S1 N2 110.21(6) . . ?
O5 S1 C8 108.65(6) . . ?
O6 S1 N2 104.08(6) . . ?
O6 S1 C8 108.85(6) . . ?
N2 S1 C8 106.02(5) . . ?
N1 O3 C5 110.95(8) . . ?
O3 N1 C1 121.69(9) . . ?
O3 N1 C4 120.44(9) . . ?
C4 N1 C1 115.38(9) . . ?
C7 N2 S1 117.91(8) . . ?
C7 N2 C21 123.65(10) . . ?
C21 N2 S1 118.16(8) . . ?
O1 C1 N1 124.74(11) . . ?
O1 C1 C2 129.47(11) . . ?
N1 C1 C2 105.79(10) . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C1 C2 C3 106.31(10) . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 105.40(10) . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
O2 C4 N1 123.49(11) . . ?
O2 C4 C3 129.94(11) . . ?
N1 C4 C3 106.55(10) . . ?
O3 C5 H5 109.2 . . ?
O3 C5 C6 108.87(9) . . ?
O3 C5 C15 103.19(9) . . ?
C6 C5 H5 109.2 . . ?
C15 C5 H5 109.2 . . ?
C15 C5 C6 116.88(9) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 C5 110.23(9) . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
O4 C7 N2 121.10(11) . . ?
O4 C7 C6 122.54(11) . . ?
N2 C7 C6 116.36(10) . . ?
C9 C8 S1 119.86(10) . . ?
C9 C8 C13 120.94(12) . . ?
C13 C8 S1 119.17(10) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.41(13) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.11(14) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 118.25(13) . . ?
C10 C11 C14 120.69(15) . . ?
C12 C11 C14 121.06(15) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.89(14) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 H13 120.8 . . ?
C12 C13 C8 118.38(13) . . ?
C12 C13 H13 120.8 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C5 117.74(11) . . ?
C16 C15 C20 118.84(12) . . ?
C20 C15 C5 123.31(11) . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.82(14) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.37(15) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.33(14) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.87(15) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 119.74(14) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
