# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ga_90606c_a
_database_code_depnum_ccdc_archive 'CCDC 1938512'
loop_
_audit_author_name
_audit_author_address
'Zhou Kaida'
;Fudan University
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O4 S'
_chemical_formula_weight         371.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.3666(5)
_cell_length_b                   8.7940(2)
_cell_length_c                   21.7751(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.8640(10)
_cell_angle_gamma                90
_cell_volume                     3644.27(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      4.91
_cell_measurement_theta_max      59.31

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.171
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30687
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.444
_diffrn_reflns_theta_max         58.997
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3972
_reflns_number_gt                3835
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0540P)²+2.5615P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00146(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3972
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.73090(2) 0.54894(4) 0.69135(2) 0.02740(12) Uani 1 1 d . . . . .
N1 N 0.60465(5) 0.45294(11) 0.77782(5) 0.0237(2) Uani 1 1 d . . . . .
O1 O 0.64170(5) 0.69767(10) 0.80837(4) 0.0311(2) Uani 1 1 d . . . . .
O2 O 0.75247(5) 0.51314(12) 0.76041(4) 0.0351(2) Uani 1 1 d . . . . .
O3 O 0.78030(5) 0.62444(13) 0.66816(5) 0.0434(3) Uani 1 1 d . . . . .
O4 O 0.65758(6) 0.49466(12) 0.54561(5) 0.0369(2) Uani 1 1 d . . . . .
C1 C 0.61782(6) 0.59991(14) 0.76648(6) 0.0239(2) Uani 1 1 d . . . . .
C2 C 0.59410(6) 0.62397(12) 0.69165(5) 0.0227(2) Uani 1 1 d . . . . .
C3 C 0.56480(6) 0.47018(12) 0.66558(6) 0.0209(2) Uani 1 1 d . . . . .
C4 C 0.53431(6) 0.41935(13) 0.60195(5) 0.0224(2) Uani 1 1 d . . . . .
H4 H 0.526156 0.487815 0.566246 0.027 Uiso 1 1 calc R U . . .
C5 C 0.51534(6) 0.26586(13) 0.59010(6) 0.0245(2) Uani 1 1 d . . . . .
C6 C 0.52838(7) 0.16931(13) 0.64366(6) 0.0287(3) Uani 1 1 d . . . . .
H6 H 0.516478 0.064848 0.635767 0.034 Uiso 1 1 calc R U . . .
C7 C 0.55829(6) 0.21945(13) 0.70873(6) 0.0269(3) Uani 1 1 d . . . . .
H7 H 0.566625 0.151538 0.744640 0.032 Uiso 1 1 calc R U . . .
C8 C 0.57521(6) 0.37197(13) 0.71853(5) 0.0217(2) Uani 1 1 d . . . . .
C9 C 0.65582(6) 0.67130(13) 0.67061(6) 0.0259(2) Uani 1 1 d . . . . .
H9A H 0.672234 0.772461 0.689937 0.031 Uiso 1 1 calc R U . . .
H9B H 0.637278 0.683989 0.622265 0.031 Uiso 1 1 calc R U . . .
C10 C 0.70935(6) 0.37125(14) 0.64985(6) 0.0260(2) Uani 1 1 d . . . . .
H10A H 0.752434 0.308232 0.663070 0.031 Uiso 1 1 calc R U . . .
H10B H 0.675208 0.318796 0.665458 0.031 Uiso 1 1 calc R U . . .
C11 C 0.67868(6) 0.37652(15) 0.57495(6) 0.0268(3) Uani 1 1 d . . . . .
C12 C 0.67611(6) 0.22912(15) 0.54042(6) 0.0259(2) Uani 1 1 d . . . . .
C13 C 0.69636(7) 0.09207(15) 0.57401(6) 0.0294(3) Uani 1 1 d . . . . .
H13 H 0.710666 0.089801 0.620558 0.035 Uiso 1 1 calc R U . . .
C14 C 0.69566(7) -0.04126(16) 0.53953(7) 0.0345(3) Uani 1 1 d . . . . .
H14 H 0.709248 -0.134680 0.562462 0.041 Uiso 1 1 calc R U . . .
C15 C 0.67506(8) -0.03774(17) 0.47142(7) 0.0371(3) Uani 1 1 d . . . . .
H15 H 0.675381 -0.128677 0.447977 0.044 Uiso 1 1 calc R U . . .
C16 C 0.65411(7) 0.09731(18) 0.43764(6) 0.0369(3) Uani 1 1 d . . . . .
H16 H 0.639540 0.098758 0.391060 0.044 Uiso 1 1 calc R U . . .
C17 C 0.65434(7) 0.23061(17) 0.47165(6) 0.0317(3) Uani 1 1 d . . . . .
H17 H 0.639703 0.323231 0.448322 0.038 Uiso 1 1 calc R U . . .
C18 C 0.53899(7) 0.75129(15) 0.67256(7) 0.0325(3) Uani 1 1 d . . . . .
H18A H 0.523660 0.769618 0.625131 0.049 Uiso 1 1 calc R U . . .
H18B H 0.559576 0.844526 0.696263 0.049 Uiso 1 1 calc R U . . .
H18C H 0.498521 0.721035 0.684090 0.049 Uiso 1 1 calc R U . . .
C19 C 0.62072(7) 0.39105(15) 0.84338(6) 0.0279(3) Uani 1 1 d . . . . .
H19A H 0.647352 0.466105 0.876025 0.042 Uiso 1 1 calc R U . . .
H19B H 0.648775 0.298311 0.848078 0.042 Uiso 1 1 calc R U . . .
H19C H 0.576884 0.366963 0.850298 0.042 Uiso 1 1 calc R U . . .
C20 C 0.48255(7) 0.20922(15) 0.52047(6) 0.0330(3) Uani 1 1 d . . . . .
H20A H 0.517264 0.213572 0.498847 0.049 Uiso 1 1 calc R U . . .
H20B H 0.442176 0.273289 0.496483 0.049 Uiso 1 1 calc R U . . .
H20C H 0.466870 0.103966 0.520817 0.049 Uiso 1 1 calc R U . . .


_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 1.4388(10) . ?
S1 O2 1.4433(9) . ?
S1 C10 1.7800(13) . ?
S1 C9 1.7910(13) . ?
N1 C1 1.3604(15) . ?
N1 C8 1.4078(14) . ?
N1 C19 1.4521(14) . ?
O1 C1 1.2214(15) . ?
O4 C11 1.2152(16) . ?
C1 C2 1.5402(15) . ?
C2 C3 1.5054(15) . ?
C2 C18 1.5343(16) . ?
C2 C9 1.5407(16) . ?
C3 C4 1.3756(16) . ?
C3 C8 1.3952(15) . ?
C4 C5 1.4025(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3896(17) . ?
C5 C20 1.5071(16) . ?
C6 C7 1.3994(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3823(16) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5253(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.4901(17) . ?
C12 C13 1.3938(18) . ?
C12 C17 1.4022(16) . ?
C13 C14 1.3896(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3904(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 O2 118.35(6) . . ?
O3 S1 C10 107.68(6) . . ?
O2 S1 C10 105.43(6) . . ?
O3 S1 C9 105.97(6) . . ?
O2 S1 C9 108.03(6) . . ?
C10 S1 C9 111.43(6) . . ?
C1 N1 C8 111.17(9) . . ?
C1 N1 C19 123.00(10) . . ?
C8 N1 C19 125.82(10) . . ?
O1 C1 N1 125.79(11) . . ?
O1 C1 C2 125.79(11) . . ?
N1 C1 C2 108.35(9) . . ?
C3 C2 C18 113.57(10) . . ?
C3 C2 C1 102.03(9) . . ?
C18 C2 C1 108.09(9) . . ?
C3 C2 C9 112.73(9) . . ?
C18 C2 C9 108.54(10) . . ?
C1 C2 C9 111.72(9) . . ?
C4 C3 C8 120.83(10) . . ?
C4 C3 C2 130.39(10) . . ?
C8 C3 C2 108.74(10) . . ?
C3 C4 C5 119.61(11) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 118.41(11) . . ?
C6 C5 C20 121.74(11) . . ?
C4 C5 C20 119.84(11) . . ?
C5 C6 C7 122.78(11) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C8 C7 C6 117.18(11) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C3 121.12(11) . . ?
C7 C8 N1 129.33(10) . . ?
C3 C8 N1 109.55(10) . . ?
C2 C9 S1 118.45(8) . . ?
C2 C9 H9A 107.7 . . ?
S1 C9 H9A 107.7 . . ?
C2 C9 H9B 107.7 . . ?
S1 C9 H9B 107.7 . . ?
H9A C9 H9B 107.1 . . ?
C11 C10 S1 116.69(9) . . ?
C11 C10 H10A 108.1 . . ?
S1 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
S1 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O4 C11 C12 122.42(11) . . ?
O4 C11 C10 121.44(11) . . ?
C12 C11 C10 116.14(10) . . ?
C13 C12 C17 119.36(12) . . ?
C13 C12 C11 122.47(10) . . ?
C17 C12 C11 118.14(11) . . ?
C14 C13 C12 120.13(12) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.91(13) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.37(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.05(12) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.17(13) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 C20 H20A 109.5 . . ?
C5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 178.16(11) . . . . ?
C19 N1 C1 O1 -2.80(19) . . . . ?
C8 N1 C1 C2 0.90(13) . . . . ?
C19 N1 C1 C2 179.94(10) . . . . ?
O1 C1 C2 C3 -175.68(11) . . . . ?
N1 C1 C2 C3 1.58(12) . . . . ?
O1 C1 C2 C18 -55.70(15) . . . . ?
N1 C1 C2 C18 121.56(11) . . . . ?
O1 C1 C2 C9 63.65(15) . . . . ?
N1 C1 C2 C9 -119.09(10) . . . . ?
C18 C2 C3 C4 62.80(16) . . . . ?
C1 C2 C3 C4 178.86(12) . . . . ?
C9 C2 C3 C4 -61.17(16) . . . . ?
C18 C2 C3 C8 -119.57(11) . . . . ?
C1 C2 C3 C8 -3.52(12) . . . . ?
C9 C2 C3 C8 116.45(11) . . . . ?
C8 C3 C4 C5 -1.90(17) . . . . ?
C2 C3 C4 C5 175.48(11) . . . . ?
C3 C4 C5 C6 -0.22(17) . . . . ?
C3 C4 C5 C20 -179.43(11) . . . . ?
C4 C5 C6 C7 1.28(18) . . . . ?
C20 C5 C6 C7 -179.52(12) . . . . ?
C5 C6 C7 C8 -0.20(18) . . . . ?
C6 C7 C8 C3 -1.96(17) . . . . ?
C6 C7 C8 N1 179.12(11) . . . . ?
C4 C3 C8 C7 3.06(17) . . . . ?
C2 C3 C8 C7 -174.83(10) . . . . ?
C4 C3 C8 N1 -177.83(10) . . . . ?
C2 C3 C8 N1 4.28(13) . . . . ?
C1 N1 C8 C7 175.72(12) . . . . ?
C19 N1 C8 C7 -3.29(19) . . . . ?
C1 N1 C8 C3 -3.29(13) . . . . ?
C19 N1 C8 C3 177.70(10) . . . . ?
C3 C2 C9 S1 -57.10(12) . . . . ?
C18 C2 C9 S1 176.19(8) . . . . ?
C1 C2 C9 S1 57.11(12) . . . . ?
O3 S1 C9 C2 -177.69(9) . . . . ?
O2 S1 C9 C2 -49.91(10) . . . . ?
C10 S1 C9 C2 65.46(10) . . . . ?
O3 S1 C10 C11 -57.73(10) . . . . ?
O2 S1 C10 C11 175.03(9) . . . . ?
C9 S1 C10 C11 58.07(10) . . . . ?
S1 C10 C11 O4 -13.61(16) . . . . ?
S1 C10 C11 C12 166.51(8) . . . . ?
O4 C11 C12 C13 -176.06(12) . . . . ?
C10 C11 C12 C13 3.82(17) . . . . ?
O4 C11 C12 C17 5.82(18) . . . . ?
C10 C11 C12 C17 -174.30(10) . . . . ?
C17 C12 C13 C14 0.73(18) . . . . ?
C11 C12 C13 C14 -177.37(12) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C16 C17 C12 0.3(2) . . . . ?
C13 C12 C17 C16 -1.05(18) . . . . ?
C11 C12 C17 C16 177.14(12) . . . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.067



