# 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_Compound
_database_code_depnum_ccdc_archive 'CCDC 1903727'
loop_
_audit_author_name
_audit_author_address
'Qiang Kang'
;Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-03-18 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N4 O4 S'
_chemical_formula_weight         422.45

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.0211(2)
_cell_length_b                   16.1241(5)
_cell_length_c                   20.6340(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2003.25(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    127(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      72.24

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    1.753
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3203
_exptl_absorpt_correction_T_max  0.7521
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      127(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\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            16910
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.479
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_full        67.079
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3543
_reflns_number_gt                3084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1198P)²+5.2408P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(13)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3543
_refine_ls_number_parameters     272
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0916
_refine_ls_wR_factor_ref         0.2394
_refine_ls_wR_factor_gt          0.2275
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_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 0.2162(4) 0.39069(13) 0.06137(12) 0.0502(6) Uani 1 1 d . . . . .
O1 O 0.3831(12) 0.2498(6) 0.1613(3) 0.072(2) Uani 1 1 d . . . . .
O2 O 0.4180(17) 0.2315(7) 0.2618(4) 0.098(4) Uani 1 1 d . . . . .
O3 O -0.1587(11) 0.3590(4) 0.2725(3) 0.0584(18) Uani 1 1 d . . . . .
O4 O 0.6466(10) 0.3880(4) 0.4658(2) 0.0436(14) Uani 1 1 d . . . . .
N1 N 0.3357(15) 0.2582(5) 0.2200(4) 0.055(2) Uani 1 1 d . . . . .
N2 N -0.1950(14) 0.3799(5) 0.2069(3) 0.0485(18) Uani 1 1 d . . . . .
N3 N 0.2535(10) 0.3559(4) 0.5921(3) 0.0318(13) Uani 1 1 d . . . . .
N4 N 0.5737(10) 0.4251(4) 0.6008(3) 0.0262(13) Uani 1 1 d . . . . .
C1 C 0.0709(18) 0.3739(5) -0.0079(4) 0.050(2) Uani 1 1 d . . . . .
H1 H 0.116989 0.391831 -0.048572 0.060 Uiso 1 1 calc R U . . .
C2 C -0.1195(16) 0.3314(5) 0.0026(4) 0.0419(19) Uani 1 1 d . . . . .
H2 H -0.217325 0.316368 -0.030219 0.050 Uiso 1 1 calc R U . . .
C3 C -0.1538(14) 0.3126(4) 0.0671(3) 0.0334(16) Uani 1 1 d . . . . .
H3 H -0.276484 0.283584 0.082446 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0149(17) 0.3416(5) 0.1060(3) 0.041(2) Uani 1 1 d . . . . .
C6 C -0.0092(14) 0.3409(5) 0.1787(4) 0.0412(19) Uani 1 1 d . . . . .
C7 C 0.1134(16) 0.3072(5) 0.2267(3) 0.0358(19) Uani 1 1 d . . . . .
C8 C 0.0263(17) 0.3185(5) 0.2844(4) 0.045(2) Uani 1 1 d . . . . .
C9 C 0.093(2) 0.2958(7) 0.3523(4) 0.073(4) Uani 1 1 d . . . . .
H9A H 0.137917 0.238063 0.352604 0.087 Uiso 1 1 calc R U . . .
H9B H -0.037333 0.300506 0.379896 0.087 Uiso 1 1 calc R U . . .
C10 C 0.284(2) 0.3487(5) 0.3829(3) 0.050(2) Uani 1 1 d . . . . .
H10 H 0.426465 0.331609 0.364420 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2800(18) 0.3285(6) 0.4557(3) 0.053(3) Uani 1 1 d . . . . .
H11A H 0.141444 0.347922 0.474322 0.063 Uiso 1 1 calc R U . . .
H11B H 0.286824 0.268839 0.461550 0.063 Uiso 1 1 calc R U . . .
C12 C 0.4748(13) 0.3690(4) 0.4915(3) 0.0312(16) Uani 1 1 d . . . . .
C13 C 0.4346(11) 0.3836(4) 0.5612(3) 0.0247(14) Uani 1 1 d . . . . .
C14 C 0.2876(14) 0.3821(5) 0.6546(3) 0.0400(18) Uani 1 1 d . . . . .
H14 H 0.189969 0.371864 0.688558 0.048 Uiso 1 1 calc R U . . .
C15 C 0.4787(14) 0.4242(5) 0.6608(3) 0.0345(17) Uani 1 1 d . . . . .
H15 H 0.534890 0.448036 0.698423 0.041 Uiso 1 1 calc R U . . .
C16 C 0.7833(13) 0.4673(5) 0.5850(4) 0.0366(17) Uani 1 1 d . . . . .
H16A H 0.898010 0.426774 0.578564 0.055 Uiso 1 1 calc R U . . .
H16B H 0.824093 0.503393 0.620064 0.055 Uiso 1 1 calc R U . . .
H16C H 0.764776 0.499283 0.546157 0.055 Uiso 1 1 calc R U . . .
C17 C 0.2431(11) 0.4382(5) 0.3679(3) 0.0318(16) Uani 1 1 d D . . . .
C18 C 0.4013(12) 0.4825(4) 0.3338(3) 0.0296(15) Uani 1 1 d D . . . .
H18 H 0.532411 0.456153 0.321839 0.036 Uiso 1 1 calc R U . . .
C19 C 0.3706(15) 0.5645(4) 0.3171(4) 0.043(2) Uani 1 1 d D . . . .
H19 H 0.482253 0.591894 0.294465 0.051 Uiso 1 1 calc R U . . .
C20 C 0.1816(14) 0.6066(6) 0.3327(4) 0.054(2) Uani 1 1 d D . . . .
H20 H 0.164510 0.662118 0.321503 0.065 Uiso 1 1 calc R U . . .
C21 C 0.0185(15) 0.5653(6) 0.3651(4) 0.060(3) Uani 1 1 d D . . . .
H21 H -0.113239 0.592419 0.375380 0.072 Uiso 1 1 calc R U . . .
C22 C 0.0480(14) 0.4825(6) 0.3829(4) 0.061(3) Uani 1 1 d D . . . .
H22 H -0.064906 0.455615 0.405387 0.074 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 C1 1.698(10) . ?
S1 C5 1.715(9) . ?
O1 N1 1.252(10) . ?
O2 N1 1.085(11) . ?
O3 C8 1.314(12) . ?
O3 N2 1.413(9) . ?
O4 C12 1.202(9) . ?
N1 C7 1.559(12) . ?
N2 C6 1.408(11) . ?
N3 C13 1.339(9) . ?
N3 C14 1.371(9) . ?
N4 C13 1.347(9) . ?
N4 C15 1.364(9) . ?
N4 C16 1.470(10) . ?
C1 C2 1.353(14) . ?
C2 C3 1.379(11) . ?
C3 C5 1.377(12) . ?
C5 C6 1.508(10) . ?
C6 C7 1.349(12) . ?
C7 C8 1.315(12) . ?
C8 C9 1.502(11) . ?
C9 C10 1.566(13) . ?
C10 C17 1.496(11) . ?
C10 C11 1.538(9) . ?
C11 C12 1.532(11) . ?
C12 C13 1.478(9) . ?
C14 C15 1.342(12) . ?
C17 C18 1.383(7) . ?
C17 C22 1.409(8) . ?
C18 C19 1.379(8) . ?
C19 C20 1.364(8) . ?
C20 C21 1.362(9) . ?
C21 C22 1.397(9) . ?

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
C1 S1 C5 90.8(4) . . ?
C8 O3 N2 115.4(7) . . ?
O2 N1 O1 128.5(9) . . ?
O2 N1 C7 121.6(8) . . ?
O1 N1 C7 109.6(7) . . ?
C6 N2 O3 99.6(7) . . ?
C13 N3 C14 102.9(6) . . ?
C13 N4 C15 106.5(6) . . ?
C13 N4 C16 129.0(6) . . ?
C15 N4 C16 124.5(6) . . ?
C2 C1 S1 112.5(6) . . ?
C1 C2 C3 113.1(8) . . ?
C5 C3 C2 112.2(7) . . ?
C3 C5 C6 120.5(8) . . ?
C3 C5 S1 111.4(5) . . ?
C6 C5 S1 127.3(7) . . ?
C7 C6 N2 108.2(7) . . ?
C7 C6 C5 132.8(8) . . ?
N2 C6 C5 118.9(8) . . ?
C8 C7 C6 113.0(9) . . ?
C8 C7 N1 119.5(8) . . ?
C6 C7 N1 127.6(7) . . ?
O3 C8 C7 103.7(8) . . ?
O3 C8 C9 121.4(10) . . ?
C7 C8 C9 134.9(10) . . ?
C8 C9 C10 116.0(8) . . ?
C17 C10 C11 113.8(7) . . ?
C17 C10 C9 108.8(8) . . ?
C11 C10 C9 105.5(7) . . ?
C12 C11 C10 111.7(7) . . ?
O4 C12 C13 122.0(7) . . ?
O4 C12 C11 123.7(6) . . ?
C13 C12 C11 114.3(6) . . ?
N3 C13 N4 112.5(6) . . ?
N3 C13 C12 122.9(6) . . ?
N4 C13 C12 124.6(6) . . ?
C15 C14 N3 112.0(7) . . ?
C14 C15 N4 106.1(6) . . ?
C18 C17 C22 115.1(7) . . ?
C18 C17 C10 119.4(7) . . ?
C22 C17 C10 125.4(7) . . ?
C19 C18 C17 122.0(7) . . ?
C20 C19 C18 122.0(8) . . ?
C21 C20 C19 118.3(8) . . ?
C20 C21 C22 120.3(8) . . ?
C21 C22 C17 122.2(8) . . ?

_refine_diff_density_max         1.320
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.093



