# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_zz
_database_code_depnum_ccdc_archive 'CCDC 2045481'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-11-20 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_audit_creation_date             2020-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_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_absolute_configuration rm
_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   16.6782(6)
_cell_length_b                   8.0492(3)
_cell_length_c                   14.5029(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1946.96(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7416
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.823
_cell_measurement_theta_min      2.530
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0966 before and 0.0570 after correction. The Ratio of minimum to maximum transmission is 0.9434. 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    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21298
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.405
_diffrn_reflns_theta_min         2.530
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE'
_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         0.829
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                3282
_reflns_number_total             3794
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.3969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0818
_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:
 C12(H12), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C20(H20), C16(H16), C17(H17), C5(H5), C2(H2), C3(H3), C1(H1), C19(H19)
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 0.43286(4) 1.02494(8) 0.45872(6) 0.02864(18) Uani 1 1 d . . . . .
O1 O 0.45115(14) 1.1661(2) 0.51511(17) 0.0369(6) Uani 1 1 d . . . . .
O2 O 0.36251(13) 1.0251(3) 0.40185(16) 0.0375(6) Uani 1 1 d . . . . .
O4 O 0.29915(13) 0.4927(2) 0.55353(16) 0.0308(5) Uani 1 1 d . . . . .
O3 O 0.21239(13) 0.6202(3) 0.45823(17) 0.0382(5) Uani 1 1 d . . . . .
N1 N 0.42410(15) 0.8684(3) 0.52867(18) 0.0273(6) Uani 1 1 d . . . . .
C8 C 0.47976(18) 0.6465(3) 0.6114(2) 0.0245(6) Uani 1 1 d . . . . .
C13 C 0.23665(18) 0.4960(4) 0.4946(2) 0.0307(7) Uani 1 1 d . . . . .
C7 C 0.46459(17) 0.5890(3) 0.5110(2) 0.0251(6) Uani 1 1 d . . . . .
H7A H 0.510045 0.613941 0.469295 0.030 Uiso 1 1 calc R . . . .
H7B H 0.449960 0.470039 0.506671 0.030 Uiso 1 1 calc R . . . .
C9 C 0.48977(19) 0.8349(4) 0.5961(2) 0.0282(7) Uani 1 1 d . . . . .
H9A H 0.482009 0.897843 0.654004 0.034 Uiso 1 1 calc R . . . .
H9B H 0.543019 0.861729 0.569834 0.034 Uiso 1 1 calc R . . . .
C12 C 0.39319(18) 0.7045(3) 0.4962(2) 0.0264(7) Uani 1 1 d . . . . .
H12 H 0.369406 0.703553 0.432877 0.032 Uiso 1 1 calc R . . . .
C4 C 0.6423(2) 0.3447(4) 0.6855(2) 0.0350(8) Uani 1 1 d . . . . .
H4 H 0.663371 0.240679 0.666268 0.042 Uiso 1 1 calc R . . . .
C10 C 0.39532(19) 0.6202(4) 0.6547(2) 0.0305(7) Uani 1 1 d . . . . .
H10A H 0.389525 0.505818 0.678854 0.037 Uiso 1 1 calc R . . . .
H10B H 0.385777 0.700061 0.705434 0.037 Uiso 1 1 calc R . . . .
C6 C 0.54763(19) 0.5673(4) 0.6639(2) 0.0263(7) Uani 1 1 d . . . . .
C20 C 0.5891(2) 1.0684(4) 0.4043(2) 0.0323(7) Uani 1 1 d . . . . .
H20 H 0.593868 1.143843 0.454418 0.039 Uiso 1 1 calc R . . . .
C15 C 0.51671(19) 0.9889(4) 0.3874(2) 0.0277(7) Uani 1 1 d . . . . .
C16 C 0.5102(2) 0.8784(4) 0.3138(2) 0.0325(8) Uani 1 1 d . . . . .
H16 H 0.460901 0.822911 0.302232 0.039 Uiso 1 1 calc R . . . .
C17 C 0.5756(2) 0.8500(4) 0.2578(2) 0.0331(8) Uani 1 1 d . . . . .
H17 H 0.570794 0.774947 0.207526 0.040 Uiso 1 1 calc R . . . .
C11 C 0.33705(18) 0.6512(4) 0.5742(2) 0.0292(7) Uani 1 1 d . . . . .
H11 H 0.296758 0.739108 0.589169 0.035 Uiso 1 1 calc R . . . .
C5 C 0.57984(19) 0.4158(4) 0.6370(2) 0.0292(7) Uani 1 1 d . . . . .
H5 H 0.558675 0.360335 0.584512 0.035 Uiso 1 1 calc R . . . .
C14 C 0.2035(2) 0.3250(4) 0.4823(3) 0.0401(9) Uani 1 1 d . . . . .
H14A H 0.247366 0.247234 0.469876 0.060 Uiso 1 1 calc GR . . . .
H14B H 0.165844 0.324328 0.430423 0.060 Uiso 1 1 calc GR . . . .
H14C H 0.175402 0.291188 0.538668 0.060 Uiso 1 1 calc GR . . . .
C18 C 0.6484(2) 0.9291(4) 0.2735(2) 0.0330(8) Uani 1 1 d . . . . .
C2 C 0.6420(2) 0.5726(5) 0.7900(3) 0.0481(10) Uani 1 1 d . . . . .
H2 H 0.662983 0.626891 0.842931 0.058 Uiso 1 1 calc R . . . .
C3 C 0.6744(2) 0.4230(4) 0.7617(3) 0.0390(8) Uani 1 1 d . . . . .
H3 H 0.718059 0.374816 0.794228 0.047 Uiso 1 1 calc R . . . .
C1 C 0.5794(2) 0.6439(4) 0.7417(2) 0.0413(9) Uani 1 1 d . . . . .
H1 H 0.557714 0.746831 0.761897 0.050 Uiso 1 1 calc R . . . .
C19 C 0.6545(2) 1.0372(4) 0.3478(2) 0.0353(8) Uani 1 1 d . . . . .
H19 H 0.704126 1.090576 0.360058 0.042 Uiso 1 1 calc R . . . .
C21 C 0.7182(2) 0.9001(5) 0.2098(3) 0.0483(9) Uani 1 1 d . . . . .
H21A H 0.720116 0.782527 0.192454 0.072 Uiso 1 1 calc GR . . . .
H21B H 0.768091 0.930645 0.241182 0.072 Uiso 1 1 calc GR . . . .
H21C H 0.711755 0.968300 0.154335 0.072 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 O1 1.433(2) . ?
S1 O2 1.434(2) . ?
S1 N1 1.624(3) . ?
S1 C15 1.763(3) . ?
O4 C13 1.348(4) . ?
O4 C11 1.454(3) . ?
O3 C13 1.201(4) . ?
N1 C9 1.493(4) . ?
N1 C12 1.493(4) . ?
C8 C7 1.549(4) . ?
C8 C9 1.542(4) . ?
C8 C10 1.557(4) . ?
C8 C6 1.506(4) . ?
C13 C14 1.495(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C12 1.526(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C11 1.530(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(4) . ?
C4 C3 1.380(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.540(4) . ?
C6 C5 1.389(4) . ?
C6 C1 1.390(5) . ?
C20 H20 0.9500 . ?
C20 C15 1.388(4) . ?
C20 C19 1.387(5) . ?
C15 C16 1.394(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(5) . ?
C11 H11 1.0000 . ?
C5 H5 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C18 C19 1.388(5) . ?
C18 C21 1.504(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(5) . ?
C2 C1 1.383(5) . ?
C3 H3 0.9500 . ?
C1 H1 0.9500 . ?
C19 H19 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
O1 S1 O2 120.13(14) . . ?
O1 S1 N1 106.12(14) . . ?
O1 S1 C15 107.24(14) . . ?
O2 S1 N1 106.63(13) . . ?
O2 S1 C15 108.17(15) . . ?
N1 S1 C15 108.06(13) . . ?
C13 O4 C11 116.7(2) . . ?
C9 N1 S1 118.90(19) . . ?
C12 N1 S1 121.3(2) . . ?
C12 N1 C9 107.5(2) . . ?
C7 C8 C10 101.0(2) . . ?
C9 C8 C7 100.1(2) . . ?
C9 C8 C10 106.8(2) . . ?
C6 C8 C7 118.2(2) . . ?
C6 C8 C9 114.1(2) . . ?
C6 C8 C10 114.7(2) . . ?
O4 C13 C14 110.1(3) . . ?
O3 C13 O4 123.7(3) . . ?
O3 C13 C14 126.2(3) . . ?
C8 C7 H7A 112.8 . . ?
C8 C7 H7B 112.8 . . ?
H7A C7 H7B 110.3 . . ?
C12 C7 C8 94.4(2) . . ?
C12 C7 H7A 112.8 . . ?
C12 C7 H7B 112.8 . . ?
N1 C9 C8 101.1(2) . . ?
N1 C9 H9A 111.5 . . ?
N1 C9 H9B 111.5 . . ?
C8 C9 H9A 111.5 . . ?
C8 C9 H9B 111.5 . . ?
H9A C9 H9B 109.4 . . ?
N1 C12 C7 103.0(2) . . ?
N1 C12 H12 115.7 . . ?
N1 C12 C11 103.1(2) . . ?
C7 C12 H12 115.7 . . ?
C7 C12 C11 101.7(2) . . ?
C11 C12 H12 115.7 . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C8 C10 H10A 110.9 . . ?
C8 C10 H10B 110.9 . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 C8 104.1(2) . . ?
C11 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C5 C6 C8 121.3(3) . . ?
C5 C6 C1 118.1(3) . . ?
C1 C6 C8 120.6(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C15 119.7(3) . . ?
C20 C15 S1 120.7(2) . . ?
C20 C15 C16 119.8(3) . . ?
C16 C15 S1 119.5(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
O4 C11 C12 111.1(2) . . ?
O4 C11 C10 106.8(2) . . ?
O4 C11 H11 111.9 . . ?
C12 C11 C10 102.7(2) . . ?
C12 C11 H11 111.9 . . ?
C10 C11 H11 111.9 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C18 C21 120.3(3) . . ?
C19 C18 C17 118.5(3) . . ?
C19 C18 C21 121.2(3) . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C6 C1 H1 119.5 . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 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'
