# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_CSM-B-93_a
_database_code_depnum_ccdc_archive 'CCDC 2114538'
loop_
_audit_author_name
_audit_author_address
'Ji-Eun Lee'
;Central for research facilities gyeongsang national university
South Korea
;
_audit_update_record             
;
2021-10-08 deposited with the CCDC.	2021-12-17 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            'C18 H17 N O3 S'
_chemical_formula_weight         327.38

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                   8.8132(12)
_cell_length_b                   18.052(3)
_cell_length_c                   10.3523(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.448(5)
_cell_angle_gamma                90
_cell_volume                     1608.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    243(2)
_cell_measurement_reflns_used    8943
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SHELXL-2014/7 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      243(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON III M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21427
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.256
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3979
_reflns_number_gt                3385
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0471P)²+0.6446P] 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         3979
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_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 0.31707(4) 0.62293(2) 0.84059(4) 0.03058(12) Uani 1 1 d . . . . .
O1 O 0.32770(13) 0.58341(6) 0.70580(11) 0.0370(3) Uani 1 1 d . . . . .
O2 O 0.22035(13) 0.68583(7) 0.80904(13) 0.0431(3) Uani 1 1 d . . . . .
O3 O 0.27724(14) 0.56539(7) 0.91990(12) 0.0421(3) Uani 1 1 d . . . . .
N1 N 0.49329(14) 0.64940(7) 0.89897(13) 0.0290(3) Uani 1 1 d . . . . .
C1 C 0.41004(18) 0.62192(8) 0.62334(16) 0.0311(3) Uani 1 1 d . . . . .
C2 C 0.3796(2) 0.59650(10) 0.49455(17) 0.0411(4) Uani 1 1 d . . . . .
H2A H 0.3056 0.5589 0.4682 0.049 Uiso 1 1 calc R U . . .
C3 C 0.4574(2) 0.62611(10) 0.40438(18) 0.0438(4) Uani 1 1 d . . . . .
C4 C 0.5659(2) 0.68126(10) 0.44751(18) 0.0428(4) Uani 1 1 d . . . . .
H4A H 0.6209 0.7019 0.3880 0.051 Uiso 1 1 calc R U . . .
C5 C 0.59439(19) 0.70629(9) 0.57620(17) 0.0372(4) Uani 1 1 d . . . . .
H5A H 0.6687 0.7438 0.6022 0.045 Uiso 1 1 calc R U . . .
C6 C 0.51636(17) 0.67775(8) 0.66949(15) 0.0295(3) Uani 1 1 d . . . . .
C7 C 0.4263(3) 0.59861(16) 0.2637(2) 0.0730(7) Uani 1 1 d . . . . .
H7A H 0.4910 0.6255 0.2149 0.109 Uiso 1 1 calc R U . . .
H7B H 0.4502 0.5462 0.2631 0.109 Uiso 1 1 calc R U . . .
H7C H 0.3178 0.6064 0.2225 0.109 Uiso 1 1 calc R U . . .
C8 C 0.55549(16) 0.70418(8) 0.81283(15) 0.0288(3) Uani 1 1 d . . . . .
C9 C 0.73193(17) 0.69598(9) 0.87180(17) 0.0365(4) Uani 1 1 d . . . . .
H9A H 0.7932 0.7115 0.8080 0.044 Uiso 1 1 calc R U . . .
H9B H 0.7633 0.7255 0.9526 0.044 Uiso 1 1 calc R U . . .
C10 C 0.75192(18) 0.61489(9) 0.90116(16) 0.0347(3) Uani 1 1 d . . . . .
C11 C 0.60768(18) 0.58871(9) 0.94251(18) 0.0375(4) Uani 1 1 d . . . . .
H11A H 0.5707 0.5419 0.8989 0.045 Uiso 1 1 calc R U . . .
H11B H 0.6268 0.5818 1.0386 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8692(2) 0.57242(12) 0.8900(2) 0.0512(5) Uani 1 1 d . . . . .
H12A H 0.9540 0.5925 0.8603 0.061 Uiso 1 1 calc R U . . .
H12B H 0.8684 0.5219 0.9116 0.061 Uiso 1 1 calc R U . . .
C13 C 0.49976(17) 0.78236(8) 0.83681(16) 0.0321(3) Uani 1 1 d . . . . .
C14 C 0.4544(2) 0.83340(9) 0.73595(18) 0.0422(4) Uani 1 1 d . . . . .
H14A H 0.4529 0.8198 0.6480 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4111(2) 0.90478(10) 0.7642(2) 0.0502(5) Uani 1 1 d . . . . .
H15A H 0.3809 0.9391 0.6952 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4120(2) 0.92534(10) 0.8918(2) 0.0490(5) Uani 1 1 d . . . . .
H16A H 0.3813 0.9734 0.9102 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4580(2) 0.87514(10) 0.9931(2) 0.0469(4) Uani 1 1 d . . . . .
H17A H 0.4593 0.8891 1.0808 0.056 Uiso 1 1 calc R U . . .
C18 C 0.5023(2) 0.80439(9) 0.96620(17) 0.0401(4) Uani 1 1 d . . . . .
H18A H 0.5346 0.7707 1.0360 0.048 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 1.4144(12) . ?
S1 O2 1.4151(12) . ?
S1 O1 1.5878(12) . ?
S1 N1 1.6127(13) . ?
O1 C1 1.4162(18) . ?
N1 C11 1.4914(19) . ?
N1 C8 1.5114(19) . ?
C1 C2 1.381(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.380(3) . ?
C2 H2A 0.9400 . ?
C3 C4 1.386(3) . ?
C3 C7 1.507(3) . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9400 . ?
C5 C6 1.399(2) . ?
C5 H5A 0.9400 . ?
C6 C8 1.526(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 C13 1.532(2) . ?
C8 C9 1.550(2) . ?
C9 C10 1.498(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C12 1.312(2) . ?
C10 C11 1.502(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9400 . ?
C12 H12B 0.9400 . ?
C13 C14 1.385(2) . ?
C13 C18 1.393(2) . ?
C14 C15 1.393(2) . ?
C14 H14A 0.9400 . ?
C15 C16 1.370(3) . ?
C15 H15A 0.9400 . ?
C16 C17 1.379(3) . ?
C16 H16A 0.9400 . ?
C17 C18 1.381(2) . ?
C17 H17A 0.9400 . ?
C18 H18A 0.9400 . ?

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 120.71(8) . . ?
O3 S1 O1 104.43(7) . . ?
O2 S1 O1 107.72(7) . . ?
O3 S1 N1 109.85(7) . . ?
O2 S1 N1 109.41(7) . . ?
O1 S1 N1 103.18(7) . . ?
C1 O1 S1 116.37(9) . . ?
C11 N1 C8 110.58(12) . . ?
C11 N1 S1 115.42(10) . . ?
C8 N1 S1 114.54(9) . . ?
C2 C1 C6 123.35(15) . . ?
C2 C1 O1 113.62(13) . . ?
C6 C1 O1 122.97(14) . . ?
C3 C2 C1 120.20(16) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 117.99(16) . . ?
C2 C3 C7 120.87(19) . . ?
C4 C3 C7 121.13(18) . . ?
C5 C4 C3 121.10(16) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 122.17(15) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C1 C6 C5 115.17(14) . . ?
C1 C6 C8 123.77(13) . . ?
C5 C6 C8 120.96(13) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C6 109.54(11) . . ?
N1 C8 C13 109.72(12) . . ?
C6 C8 C13 115.63(12) . . ?
N1 C8 C9 99.54(11) . . ?
C6 C8 C9 110.51(13) . . ?
C13 C8 C9 110.71(12) . . ?
C10 C9 C8 103.74(12) . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C12 C10 C9 127.86(17) . . ?
C12 C10 C11 124.92(16) . . ?
C9 C10 C11 107.19(13) . . ?
N1 C11 C10 103.95(12) . . ?
N1 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
N1 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C10 C12 H12A 120.0 . . ?
C10 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C14 C13 C18 118.51(15) . . ?
C14 C13 C8 122.75(15) . . ?
C18 C13 C8 118.65(14) . . ?
C13 C14 C15 120.30(17) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C16 C15 C14 120.54(17) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 119.64(17) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
C16 C17 C18 120.25(18) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C17 C18 C13 120.75(17) . . ?
C17 C18 H18A 119.6 . . ?
C13 C18 H18A 119.6 . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.044

