# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_d8v21755_0m
_audit_block_doi                 10.5517/ccdc.csd.cc28zr89
_database_code_depnum_ccdc_archive 'CCDC 2114921'
loop_
_audit_author_name
_audit_author_address
'Chen Lu'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N O3 S'
_chemical_formula_weight         277.33

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.3951(5)
_cell_length_b                   8.7516(4)
_cell_length_c                   14.2044(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.6710(10)
_cell_angle_gamma                90
_cell_volume                     1285.90(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    8979
_cell_measurement_theta_min      5.104
_cell_measurement_theta_max      54.983

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.255
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            12404
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2501
_reflns_number_gt                2312
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0389P)²+0.7064P] 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         2501
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.82557(3) 0.64179(4) 0.52735(2) 0.02439(13) Uani 1 1 d . . . . .
O1 O 0.40032(12) 0.6492(2) 0.28752(9) 0.0534(4) Uani 1 1 d . . . . .
O2 O 0.91914(11) 0.76215(14) 0.52127(9) 0.0371(3) Uani 1 1 d . . . . .
O3 O 0.31987(10) 0.90807(14) 0.56319(8) 0.0340(3) Uani 1 1 d . . . . .
N1 N 0.81791(13) 0.52312(17) 0.44503(9) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.71877(15) 0.52364(18) 0.37479(10) 0.0258(3) Uani 1 1 d . . . . .
C2 C 0.75356(18) 0.4327(2) 0.29089(12) 0.0385(4) Uani 1 1 d . . . . .
H2A H 0.8080 0.4960 0.2540 0.046 Uiso 1 1 calc R U . . .
H2B H 0.8048 0.3439 0.3139 0.046 Uiso 1 1 calc R U . . .
C3 C 0.64000(19) 0.3784(2) 0.22741(13) 0.0418(4) Uani 1 1 d . . . . .
H3A H 0.5977 0.2942 0.2577 0.050 Uiso 1 1 calc R U . . .
H3B H 0.6689 0.3405 0.1681 0.050 Uiso 1 1 calc R U . . .
C4 C 0.54573(19) 0.5071(3) 0.20693(12) 0.0476(5) Uani 1 1 d . . . . .
H4A H 0.4676 0.4664 0.1713 0.057 Uiso 1 1 calc R U . . .
H4B H 0.5839 0.5817 0.1664 0.057 Uiso 1 1 calc R U . . .
C5 C 0.50728(15) 0.5883(2) 0.29337(11) 0.0317(4) Uani 1 1 d . . . . .
C6 C 0.60093(14) 0.59682(17) 0.37744(10) 0.0227(3) Uani 1 1 d . . . . .
C7 C 0.57462(13) 0.68487(17) 0.46141(10) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.67192(13) 0.71098(17) 0.53619(10) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.65224(15) 0.80188(19) 0.61451(10) 0.0282(3) Uani 1 1 d . . . . .
H9 H 0.7201 0.8176 0.6624 0.034 Uiso 1 1 calc R U . . .
C10 C 0.53439(15) 0.86769(19) 0.62137(11) 0.0294(3) Uani 1 1 d . . . . .
H10 H 0.5207 0.9306 0.6731 0.035 Uiso 1 1 calc R U . . .
C11 C 0.43406(14) 0.83980(18) 0.54994(11) 0.0259(3) Uani 1 1 d . . . . .
C12 C 0.45326(14) 0.75051(17) 0.47251(10) 0.0243(3) Uani 1 1 d . . . . .
H12 H 0.3839 0.7331 0.4261 0.029 Uiso 1 1 calc R U . . .
C13 C 0.87193(16) 0.5363(2) 0.63036(12) 0.0349(4) Uani 1 1 d . . . . .
H13A H 0.9521 0.4828 0.6231 0.052 Uiso 1 1 calc R U . . .
H13B H 0.8049 0.4629 0.6408 0.052 Uiso 1 1 calc R U . . .
H13C H 0.8844 0.6051 0.6840 0.052 Uiso 1 1 calc R U . . .
C14 C 0.21249(15) 0.8820(2) 0.49358(12) 0.0328(4) Uani 1 1 d . . . . .
H14A H 0.2370 0.9079 0.4314 0.049 Uiso 1 1 calc R U . . .
H14B H 0.1402 0.9451 0.5077 0.049 Uiso 1 1 calc R U . . .
H14C H 0.1877 0.7752 0.4946 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 O2 1.4421(12) . ?
S1 N1 1.5600(14) . ?
S1 C8 1.7242(14) . ?
S1 C13 1.7566(16) . ?
O1 C5 1.228(2) . ?
O3 C11 1.3586(18) . ?
O3 C14 1.4344(19) . ?
N1 C1 1.362(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.507(2) . ?
C2 C3 1.491(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.502(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.506(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.466(2) . ?
C6 C7 1.468(2) . ?
C7 C12 1.409(2) . ?
C7 C8 1.4112(19) . ?
C8 C9 1.399(2) . ?
C9 C10 1.366(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.403(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.380(2) . ?
C12 H12 0.9400 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 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 N1 115.23(8) . . ?
O2 S1 C8 112.52(7) . . ?
N1 S1 C8 108.02(7) . . ?
O2 S1 C13 107.60(8) . . ?
N1 S1 C13 105.31(8) . . ?
C8 S1 C13 107.67(7) . . ?
C11 O3 C14 117.74(12) . . ?
C1 N1 S1 121.73(11) . . ?
N1 C1 C6 126.05(13) . . ?
N1 C1 C2 110.76(13) . . ?
C6 C1 C2 123.19(14) . . ?
C3 C2 C1 114.15(15) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 109.93(16) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 114.61(15) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
O1 C5 C6 123.83(15) . . ?
O1 C5 C4 117.45(14) . . ?
C6 C5 C4 118.65(14) . . ?
C1 C6 C5 118.16(13) . . ?
C1 C6 C7 120.04(13) . . ?
C5 C6 C7 121.76(13) . . ?
C12 C7 C8 115.64(13) . . ?
C12 C7 C6 123.07(13) . . ?
C8 C7 C6 121.29(13) . . ?
C9 C8 C7 122.71(13) . . ?
C9 C8 S1 117.83(11) . . ?
C7 C8 S1 119.24(11) . . ?
C10 C9 C8 119.94(13) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 118.88(14) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
O3 C11 C12 123.83(14) . . ?
O3 C11 C10 114.87(14) . . ?
C12 C11 C10 121.29(14) . . ?
C11 C12 C7 121.45(13) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O2 S1 N1 C1 -104.74(14) . . . . ?
C8 S1 N1 C1 22.02(15) . . . . ?
C13 S1 N1 C1 136.86(14) . . . . ?
S1 N1 C1 C6 -17.0(2) . . . . ?
S1 N1 C1 C2 162.79(13) . . . . ?
N1 C1 C2 C3 158.52(16) . . . . ?
C6 C1 C2 C3 -21.7(2) . . . . ?
C1 C2 C3 C4 47.0(2) . . . . ?
C2 C3 C4 C5 -51.9(2) . . . . ?
C3 C4 C5 O1 -152.43(19) . . . . ?
C3 C4 C5 C6 30.5(3) . . . . ?
N1 C1 C6 C5 178.11(15) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
N1 C1 C6 C7 0.5(2) . . . . ?
C2 C1 C6 C7 -179.30(15) . . . . ?
O1 C5 C6 C1 -179.65(18) . . . . ?
C4 C5 C6 C1 -2.8(2) . . . . ?
O1 C5 C6 C7 -2.1(3) . . . . ?
C4 C5 C6 C7 174.79(16) . . . . ?
C1 C6 C7 C12 -174.10(14) . . . . ?
C5 C6 C7 C12 8.4(2) . . . . ?
C1 C6 C7 C8 6.9(2) . . . . ?
C5 C6 C7 C8 -170.60(14) . . . . ?
C12 C7 C8 C9 -2.9(2) . . . . ?
C6 C7 C8 C9 176.10(14) . . . . ?
C12 C7 C8 S1 -177.50(11) . . . . ?
C6 C7 C8 S1 1.5(2) . . . . ?
O2 S1 C8 C9 -61.15(14) . . . . ?
N1 S1 C8 C9 170.52(12) . . . . ?
C13 S1 C8 C9 57.25(14) . . . . ?
O2 S1 C8 C7 113.68(13) . . . . ?
N1 S1 C8 C7 -14.65(14) . . . . ?
C13 S1 C8 C7 -127.92(13) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
S1 C8 C9 C10 175.61(13) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C14 O3 C11 C12 1.7(2) . . . . ?
C14 O3 C11 C10 -178.89(14) . . . . ?
C9 C10 C11 O3 179.13(15) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
O3 C11 C12 C7 178.71(14) . . . . ?
C10 C11 C12 C7 -0.6(2) . . . . ?
C8 C7 C12 C11 2.7(2) . . . . ?
C6 C7 C12 C11 -176.28(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14B O2 0.97 2.66 3.400(2) 133.7 3_676
C13 H13C O1 0.97 2.60 3.537(3) 162.4 4_676
C13 H13B O1 0.97 2.64 3.558(2) 157.6 3_666
C13 H13A N1 0.97 2.67 3.535(2) 149.1 3_766
C12 H12 O1 0.94 2.12 2.7763(19) 125.4 .
C9 H9 O1 0.94 2.47 3.4088(19) 178.2 4_676
C9 H9 O1 0.94 2.47 3.4088(19) 178.2 4_676
C12 H12 O1 0.94 2.12 2.7763(19) 125.4 .
C13 H13A N1 0.97 2.67 3.535(2) 149.1 3_766
C13 H13B O1 0.97 2.64 3.558(2) 157.6 3_666
C13 H13C O1 0.97 2.60 3.537(3) 162.4 4_676
C14 H14B O2 0.97 2.66 3.400(2) 133.7 3_676

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

