# Electronic Supplementary Material (ESI) for ChemComm.
# 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 
# this file and to allow appropriate attribution of the data. 
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data_cu190930c
_database_code_depnum_ccdc_archive 'CCDC 1971018'
loop_
_audit_author_name
_audit_author_address
'junhan ma'
;Hangzhou normal university
China
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O4 S'
_chemical_formula_sum            'C21 H23 N O4 S'
_chemical_formula_weight         385.46
_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 0.0181 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      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                   6.8902(4)
_cell_length_b                   11.3752(7)
_cell_length_c                   12.5546(8)
_cell_angle_alpha                77.459(2)
_cell_angle_beta                 83.636(2)
_cell_angle_gamma                81.818(2)
_cell_volume                     947.48(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      70.71
_cell_measurement_theta_min      3.62
_shelx_estimated_absorpt_T_max   0.722
_shelx_estimated_absorpt_T_min   0.670
_exptl_absorpt_coefficient_mu    1.744
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1343 before and 0.0446 after correction. The Ratio of minimum to maximum transmission is 0.7276. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16811
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.702
_diffrn_reflns_theta_min         3.619
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3246
_reflns_number_total             3367
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.047
_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)+(0.0518P)²+0.2688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1019
_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:
 C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.56626(6) 0.55149(3) 0.83656(3) 0.04263(14) Uani 1 1 d . . . . .
O1 O 0.89176(18) 0.56922(13) 0.64963(11) 0.0621(3) Uani 1 1 d . . . . .
O2 O 0.69167(19) 0.43957(10) 0.84757(10) 0.0569(3) Uani 1 1 d . . . . .
O3 O 0.36400(17) 0.55336(11) 0.87681(9) 0.0535(3) Uani 1 1 d . . . . .
O4 O 0.8897(2) 0.86546(12) 1.06799(12) 0.0656(4) Uani 1 1 d . . . . .
N1 N 0.56055(18) 0.61156(11) 0.70362(10) 0.0409(3) Uani 1 1 d . . . . .
C1 C 0.7238(2) 0.60080(14) 0.62738(13) 0.0448(3) Uani 1 1 d . . . . .
C2 C 0.6427(3) 0.63530(13) 0.51960(13) 0.0464(4) Uani 1 1 d . . . . .
C3 C 0.7410(3) 0.62914(16) 0.41800(15) 0.0617(5) Uani 1 1 d . . . . .
H3 H 0.8760 0.6062 0.4104 0.074 Uiso 1 1 calc R . . . .
C4 C 0.6299(4) 0.65856(17) 0.32839(15) 0.0743(7) Uani 1 1 d . . . . .
H4 H 0.6911 0.6564 0.2589 0.089 Uiso 1 1 calc R . . . .
C5 C 0.4301(4) 0.69096(17) 0.34119(16) 0.0752(7) Uani 1 1 d . . . . .
H5 H 0.3587 0.7097 0.2798 0.090 Uiso 1 1 calc R . . . .
C6 C 0.3317(3) 0.69661(16) 0.44256(15) 0.0620(5) Uani 1 1 d . . . . .
H6 H 0.1964 0.7183 0.4500 0.074 Uiso 1 1 calc R . . . .
C7 C 0.4426(3) 0.66861(13) 0.53310(13) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.3749(2) 0.66502(12) 0.65182(12) 0.0409(3) Uani 1 1 d . . . . .
H8 H 0.2752 0.6092 0.6754 0.049 Uiso 1 1 calc R . . . .
C9 C 0.6737(2) 0.65063(13) 0.89511(12) 0.0420(3) Uani 1 1 d . . . . .
C10 C 0.5527(3) 0.74172(16) 0.93625(16) 0.0567(4) Uani 1 1 d . . . . .
H10 H 0.4191 0.7548 0.9261 0.068 Uiso 1 1 calc R . . . .
C11 C 0.6316(3) 0.81246(17) 0.99194(17) 0.0613(5) Uani 1 1 d . . . . .
H11 H 0.5511 0.8743 1.0187 0.074 Uiso 1 1 calc R . . . .
C12 C 0.8291(3) 0.79251(14) 1.00859(13) 0.0486(4) Uani 1 1 d . . . . .
C13 C 0.9508(3) 0.70190(15) 0.96719(14) 0.0494(4) Uani 1 1 d . . . . .
H13 H 1.0843 0.6887 0.9778 0.059 Uiso 1 1 calc R . . . .
C14 C 0.8717(2) 0.63131(14) 0.90993(13) 0.0462(4) Uani 1 1 d . . . . .
H14 H 0.9524 0.5708 0.8815 0.055 Uiso 1 1 calc R . . . .
C15 C 1.0911(3) 0.8514(2) 1.0858(2) 0.0835(7) Uani 1 1 d . . . . .
H15A H 1.1674 0.8692 1.0167 0.125 Uiso 1 1 calc GR . . . .
H15B H 1.1303 0.7694 1.1220 0.125 Uiso 1 1 calc GR . . . .
H15C H 1.1125 0.9060 1.1306 0.125 Uiso 1 1 calc GR . . . .
C16 C 0.2966(2) 0.78886(13) 0.68156(13) 0.0424(3) Uani 1 1 d . . . . .
H16 H 0.2757 0.7745 0.7616 0.051 Uiso 1 1 calc R . . . .
C17 C 0.0984(3) 0.84021(15) 0.63775(17) 0.0575(4) Uani 1 1 d . . . . .
H17A H 0.0065 0.7808 0.6622 0.069 Uiso 1 1 calc R . . . .
H17B H 0.1127 0.8570 0.5583 0.069 Uiso 1 1 calc R . . . .
C18 C 0.0173(3) 0.95662(17) 0.6774(2) 0.0682(5) Uani 1 1 d . . . . .
H18A H -0.1060 0.9898 0.6457 0.082 Uiso 1 1 calc R . . . .
H18B H -0.0088 0.9383 0.7564 0.082 Uiso 1 1 calc R . . . .
C19 C 0.1612(3) 1.04999(16) 0.64564(19) 0.0696(5) Uani 1 1 d . . . . .
H19A H 0.1743 1.0759 0.5666 0.084 Uiso 1 1 calc R . . . .
H19B H 0.1100 1.1205 0.6765 0.084 Uiso 1 1 calc R . . . .
C20 C 0.3607(3) 0.99979(16) 0.68567(19) 0.0652(5) Uani 1 1 d . . . . .
H20A H 0.3507 0.9843 0.7651 0.078 Uiso 1 1 calc R . . . .
H20B H 0.4514 1.0596 0.6588 0.078 Uiso 1 1 calc R . . . .
C21 C 0.4419(3) 0.88236(14) 0.64735(16) 0.0522(4) Uani 1 1 d . . . . .
H21A H 0.4670 0.8994 0.5683 0.063 Uiso 1 1 calc R . . . .
H21B H 0.5656 0.8497 0.6788 0.063 Uiso 1 1 calc R . . . .


_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 O2 1.4225(11) . ?
S1 O3 1.4276(12) . ?
S1 N1 1.6631(12) . ?
S1 C9 1.7545(16) . ?
O1 C1 1.207(2) . ?
O4 C12 1.362(2) . ?
O4 C15 1.411(3) . ?
N1 C1 1.403(2) . ?
N1 C8 1.4902(19) . ?
C1 C2 1.474(2) . ?
C2 C3 1.387(2) . ?
C2 C7 1.379(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(2) . ?
C7 C8 1.505(2) . ?
C8 H8 0.9800 . ?
C8 C16 1.543(2) . ?
C9 C10 1.388(2) . ?
C9 C14 1.377(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C12 C13 1.388(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.519(2) . ?
C16 C21 1.525(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.525(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.516(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.508(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.528(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
O2 S1 O3 120.09(8) . . ?
O2 S1 N1 107.77(7) . . ?
O2 S1 C9 108.16(7) . . ?
O3 S1 N1 104.31(7) . . ?
O3 S1 C9 108.68(7) . . ?
N1 S1 C9 107.13(7) . . ?
C12 O4 C15 118.15(14) . . ?
C1 N1 S1 123.21(11) . . ?
C1 N1 C8 113.26(12) . . ?
C8 N1 S1 122.90(10) . . ?
O1 C1 N1 125.36(15) . . ?
O1 C1 C2 129.60(15) . . ?
N1 C1 C2 105.04(13) . . ?
C3 C2 C1 127.82(17) . . ?
C7 C2 C1 109.60(14) . . ?
C7 C2 C3 122.44(17) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 C2 117.3(2) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.64(19) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.10(19) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.7(2) . . ?
C7 C6 H6 121.2 . . ?
C2 C7 C6 119.80(17) . . ?
C2 C7 C8 111.14(13) . . ?
C6 C7 C8 129.03(17) . . ?
N1 C8 C7 100.40(12) . . ?
N1 C8 H8 109.7 . . ?
N1 C8 C16 111.34(12) . . ?
C7 C8 H8 109.7 . . ?
C7 C8 C16 115.61(12) . . ?
C16 C8 H8 109.7 . . ?
C10 C9 S1 118.81(13) . . ?
C14 C9 S1 120.62(11) . . ?
C14 C9 C10 120.25(15) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.61(16) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.51(15) . . ?
C12 C11 H11 119.7 . . ?
O4 C12 C11 115.41(14) . . ?
O4 C12 C13 124.49(16) . . ?
C11 C12 C13 120.09(15) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.41(16) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 120.12(14) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16 106.7 . . ?
C17 C16 C8 112.33(13) . . ?
C17 C16 H16 106.7 . . ?
C17 C16 C21 110.47(13) . . ?
C21 C16 C8 113.51(13) . . ?
C21 C16 H16 106.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 C18 110.80(16) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111.22(17) . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 C18 111.64(16) . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C19 C20 C21 111.77(16) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C16 C21 C20 110.76(15) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
