# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_SUST_2021_0ma
_database_code_depnum_ccdc_archive 'CCDC 1954135'
loop_
_audit_author_name
_audit_author_address
chenpu
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.7962(4)
_cell_length_b                   16.1392(14)
_cell_length_c                   15.9437(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1234.15(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    276(2)
_cell_measurement_reflns_used    1453
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      19.68

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      276(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            11880
_diffrn_reflns_av_unetI/netI     0.2754
_diffrn_reflns_av_R_equivalents  0.2035
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         28.401
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.900
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.900
_reflns_number_total             2855
_reflns_number_gt                878
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)] 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_number_reflns         2855
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2812
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_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
C1 C 0.0917(7) 0.2078(2) 0.0778(2) 0.0473(10) Uani 1 1 d . . . . .
C2 C -0.0596(8) 0.1866(3) 0.1501(2) 0.0634(11) Uani 1 1 d . . . . .
H2 H -0.0322 0.2162 0.1994 0.076 Uiso 1 1 calc R U . . .
C3 C -0.2455(8) 0.1231(3) 0.1484(3) 0.0705(12) Uani 1 1 d . . . . .
H3 H -0.3452 0.1093 0.1965 0.085 Uiso 1 1 calc R U . . .
C4 C -0.2862(9) 0.0788(3) 0.0744(3) 0.0712(12) Uani 1 1 d . . . . .
H4 H -0.4122 0.0350 0.0737 0.085 Uiso 1 1 calc R U . . .
C5 C -0.1456(8) 0.0985(2) 0.0039(2) 0.0646(11) Uani 1 1 d . . . . .
H5 H -0.1797 0.0688 -0.0450 0.077 Uiso 1 1 calc R U . . .
C6 C 0.0515(7) 0.1631(2) 0.0029(2) 0.0485(10) Uani 1 1 d . . . . .
C7 C 0.2118(8) 0.1866(2) -0.0683(2) 0.0528(10) Uani 1 1 d . . . . .
C8 C 0.2192(9) 0.1513(3) -0.1505(2) 0.0728(13) Uani 1 1 d . . . . .
H8 H 0.1140 0.1057 -0.1670 0.087 Uiso 1 1 calc R U . . .
C9 C 0.3971(9) 0.1922(3) -0.2010(2) 0.0780(14) Uani 1 1 d . . . . .
H9 H 0.4244 0.1779 -0.2570 0.094 Uiso 1 1 calc R U . . .
C10 C 0.3920(8) 0.2529(2) -0.06109(19) 0.0502(10) Uani 1 1 d . . . . .
C11 C 0.4194(8) 0.2941(2) 0.0168(2) 0.0496(10) Uani 1 1 d . . . . .
C12 C 0.6237(8) 0.3640(3) 0.0238(2) 0.0620(11) Uani 1 1 d . . . . .
C13 C 0.8277(12) 0.4648(3) 0.1105(3) 0.1111(18) Uani 1 1 d . . . . .
H13A H 1.0170 0.4436 0.1098 0.133 Uiso 1 1 calc R U . . .
H13B H 0.8081 0.5045 0.0653 0.133 Uiso 1 1 calc R U . . .
C14 C 0.7721(13) 0.5037(3) 0.1886(3) 0.127(2) Uani 1 1 d . . . . .
H14A H 0.5782 0.5182 0.1916 0.190 Uiso 1 1 calc R U . . .
H14B H 0.8835 0.5528 0.1936 0.190 Uiso 1 1 calc R U . . .
H14C H 0.8169 0.4663 0.2334 0.190 Uiso 1 1 calc R U . . .
N1 N 0.2777(6) 0.27289(18) 0.08393(15) 0.0506(8) Uani 1 1 d . . . . .
O1 O 0.6302(6) 0.39700(17) 0.09927(16) 0.0765(9) Uani 1 1 d . . . . .
O2 O 0.7619(7) 0.3869(2) -0.03442(16) 0.0973(11) Uani 1 1 d . . . . .
S1 S 0.5675(3) 0.27178(7) -0.15408(6) 0.0736(4) Uani 1 1 d . . . . .


_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
C1 N1 1.381(4) . ?
C1 C2 1.404(4) . ?
C1 C6 1.409(4) . ?
C2 C3 1.359(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.349(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.422(4) . ?
C7 C10 1.381(5) . ?
C7 C8 1.429(4) . ?
C8 C9 1.347(5) . ?
C8 H8 0.9300 . ?
C9 S1 1.697(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.414(4) . ?
C10 S1 1.732(3) . ?
C11 N1 1.314(4) . ?
C11 C12 1.497(5) . ?
C12 O2 1.199(4) . ?
C12 O1 1.317(4) . ?
C13 C14 1.420(5) . ?
C13 O1 1.458(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
N1 C1 C2 117.5(3) . . ?
N1 C1 C6 122.5(3) . . ?
C2 C1 C6 120.0(3) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.4(3) . . ?
C5 C6 C7 124.8(3) . . ?
C1 C6 C7 117.8(3) . . ?
C10 C7 C6 118.6(3) . . ?
C10 C7 C8 111.7(3) . . ?
C6 C7 C8 129.7(4) . . ?
C9 C8 C7 111.7(4) . . ?
C9 C8 H8 124.2 . . ?
C7 C8 H8 124.2 . . ?
C8 C9 S1 114.3(3) . . ?
C8 C9 H9 122.8 . . ?
S1 C9 H9 122.8 . . ?
C7 C10 C11 119.7(3) . . ?
C7 C10 S1 111.7(3) . . ?
C11 C10 S1 128.6(3) . . ?
N1 C11 C10 123.0(3) . . ?
N1 C11 C12 118.3(3) . . ?
C10 C11 C12 118.7(3) . . ?
O2 C12 O1 124.7(4) . . ?
O2 C12 C11 122.4(4) . . ?
O1 C12 C11 112.9(3) . . ?
C14 C13 O1 108.5(4) . . ?
C14 C13 H13A 110.0 . . ?
O1 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
O1 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 N1 C1 118.3(3) . . ?
C12 O1 C13 115.6(3) . . ?
C9 S1 C10 90.60(19) . . ?

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
N1 C1 C2 C3 -179.9(3) . . . . ?
C6 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 1.4(6) . . . . ?
C4 C5 C6 C1 -1.5(5) . . . . ?
C4 C5 C6 C7 178.7(4) . . . . ?
N1 C1 C6 C5 -179.4(3) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
N1 C1 C6 C7 0.3(5) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
C5 C6 C7 C10 178.1(3) . . . . ?
C1 C6 C7 C10 -1.7(5) . . . . ?
C5 C6 C7 C8 -2.0(6) . . . . ?
C1 C6 C7 C8 178.2(4) . . . . ?
C10 C7 C8 C9 -0.9(5) . . . . ?
C6 C7 C8 C9 179.2(4) . . . . ?
C7 C8 C9 S1 1.3(5) . . . . ?
C6 C7 C10 C11 1.9(5) . . . . ?
C8 C7 C10 C11 -178.0(4) . . . . ?
C6 C7 C10 S1 -180.0(3) . . . . ?
C8 C7 C10 S1 0.1(4) . . . . ?
C7 C10 C11 N1 -0.7(6) . . . . ?
S1 C10 C11 N1 -178.5(3) . . . . ?
C7 C10 C11 C12 177.9(3) . . . . ?
S1 C10 C11 C12 0.1(5) . . . . ?
N1 C11 C12 O2 179.7(4) . . . . ?
C10 C11 C12 O2 1.0(6) . . . . ?
N1 C11 C12 O1 -1.2(5) . . . . ?
C10 C11 C12 O1 -179.8(3) . . . . ?
C10 C11 N1 C1 -0.6(5) . . . . ?
C12 C11 N1 C1 -179.2(3) . . . . ?
C2 C1 N1 C11 -179.4(3) . . . . ?
C6 C1 N1 C11 0.8(5) . . . . ?
O2 C12 O1 C13 -1.6(6) . . . . ?
C11 C12 O1 C13 179.3(3) . . . . ?
C14 C13 O1 C12 168.8(4) . . . . ?
C8 C9 S1 C10 -1.0(3) . . . . ?
C7 C10 S1 C9 0.5(3) . . . . ?
C11 C10 S1 C9 178.4(4) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.041

