# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ysr32a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2109891'
loop_
_audit_author_name
_audit_author_address
Mahesh
;University of Hyderabad
India
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N O S'
_chemical_formula_sum            'C22 H17 N O S'
_chemical_formula_weight         343.42
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.472(2)
_cell_length_b                   10.980(3)
_cell_length_c                   12.170(4)
_cell_angle_alpha                115.159(12)
_cell_angle_beta                 102.060(13)
_cell_angle_gamma                95.668(13)
_cell_volume                     863.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3248
_cell_measurement_temperature    298.22
_cell_measurement_theta_max      23.96
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1666 before and 0.0789 after correction.
The Ratio of minimum to maximum transmission is 0.8944.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2059
_diffrn_reflns_av_unetI/netI     0.1347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.750
_diffrn_reflns_theta_min         2.852
_diffrn_ambient_temperature      298.22
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1946
_reflns_number_total             4034
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.0779
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+0.7274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1640
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C16(H16), C2(H2), C14(H14), C15(H15), C18(H18), C3(H3),
 C22(H22), C6(H6), C4(H4), C19(H19), C20(H20), C21(H21), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.91136(16) 0.53267(11) 0.29576(11) 0.0821(5) Uani 1 1 d . . . . .
O1 O 0.4694(3) 0.8213(2) 0.3835(2) 0.0523(7) Uani 1 1 d . . . . .
N1 N 0.7233(4) 0.9558(3) 0.5508(2) 0.0456(8) Uani 1 1 d . . . . .
H1 H 0.672655 1.024066 0.585931 0.055 Uiso 1 1 calc R . . . .
C10 C 0.6327(5) 0.8398(3) 0.4428(3) 0.0414(8) Uani 1 1 d . . . . .
C1 C 0.4305(4) 0.4447(3) 0.2104(3) 0.0428(9) Uani 1 1 d . . . . .
C9 C 0.7684(4) 0.7480(3) 0.4159(3) 0.0384(8) Uani 1 1 d . . . . .
C12 C 0.9072(5) 0.9513(3) 0.5978(3) 0.0393(8) Uani 1 1 d . . . . .
C7 C 0.5493(5) 0.5645(3) 0.2107(3) 0.0438(9) Uani 1 1 d . . . . .
H7A H 0.574194 0.534286 0.129091 0.053 Uiso 1 1 calc R . . . .
H7B H 0.478849 0.636386 0.221625 0.053 Uiso 1 1 calc R . . . .
C11 C 0.9423(5) 0.8241(3) 0.5194(3) 0.0383(8) Uani 1 1 d . . . . .
C13 C 1.0416(5) 1.0509(3) 0.7019(3) 0.0486(9) Uani 1 1 d . . . . .
H13 H 1.015283 1.134525 0.752194 0.058 Uiso 1 1 calc R . . . .
C17 C 0.8256(5) 0.3874(3) 0.1470(3) 0.0479(9) Uani 1 1 d . . . . .
C16 C 1.1199(5) 0.8000(4) 0.5499(3) 0.0497(9) Uani 1 1 d . . . . .
H16 H 1.147818 0.716764 0.500059 0.060 Uiso 1 1 calc R . . . .
C8 C 0.7336(5) 0.6243(3) 0.3126(3) 0.0409(8) Uani 1 1 d . . . . .
C2 C 0.3337(5) 0.3323(4) 0.0981(4) 0.0544(10) Uani 1 1 d . . . . .
H2 H 0.342412 0.330790 0.022406 0.065 Uiso 1 1 calc R . . . .
C14 C 1.2168(5) 1.0234(4) 0.7296(3) 0.0549(10) Uani 1 1 d . . . . .
H14 H 1.309958 1.089148 0.799912 0.066 Uiso 1 1 calc R . . . .
C15 C 1.2554(5) 0.9000(4) 0.6545(3) 0.0575(10) Uani 1 1 d . . . . .
H15 H 1.374681 0.883598 0.674614 0.069 Uiso 1 1 calc R . . . .
C18 C 0.8313(6) 0.3968(5) 0.0390(4) 0.0708(12) Uani 1 1 d . . . . .
H18 H 0.872089 0.482080 0.043538 0.085 Uiso 1 1 calc R . . . .
C3 C 0.2243(5) 0.2219(4) 0.0951(5) 0.0667(12) Uani 1 1 d . . . . .
H3 H 0.161012 0.146386 0.018247 0.080 Uiso 1 1 calc R . . . .
C22 C 0.7643(5) 0.2617(4) 0.1383(4) 0.0667(12) Uani 1 1 d . . . . .
H22 H 0.759040 0.253678 0.210721 0.080 Uiso 1 1 calc R . . . .
C6 C 0.4110(6) 0.4450(5) 0.3193(4) 0.0785(14) Uani 1 1 d . . . . .
H6 H 0.472671 0.520497 0.396637 0.094 Uiso 1 1 calc R . . . .
C4 C 0.2094(6) 0.2240(5) 0.2044(5) 0.0799(14) Uani 1 1 d . . . . .
H4 H 0.136217 0.149611 0.203148 0.096 Uiso 1 1 calc R . . . .
C19 C 0.7778(8) 0.2821(7) -0.0748(4) 0.103(2) Uani 1 1 d . . . . .
H19 H 0.781752 0.289509 -0.147673 0.124 Uiso 1 1 calc R . . . .
C20 C 0.7192(7) 0.1580(7) -0.0826(6) 0.113(3) Uani 1 1 d . . . . .
H20 H 0.684751 0.079867 -0.160606 0.135 Uiso 1 1 calc R . . . .
C21 C 0.7101(6) 0.1464(4) 0.0225(7) 0.0955(19) Uani 1 1 d . . . . .
H21 H 0.667245 0.060761 0.016484 0.115 Uiso 1 1 calc R . . . .
C5 C 0.3016(7) 0.3350(6) 0.3162(5) 0.1019(18) Uani 1 1 d . . . . .
H5 H 0.290279 0.336532 0.391438 0.122 Uiso 1 1 calc R . . . .


_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 C17 1.758(3) . ?
S1 C8 1.738(3) . ?
O1 C10 1.229(4) . ?
N1 C10 1.357(4) . ?
N1 C12 1.388(4) . ?
C10 C9 1.487(4) . ?
C1 C7 1.510(5) . ?
C1 C2 1.376(4) . ?
C1 C6 1.362(5) . ?
C9 C11 1.477(4) . ?
C9 C8 1.354(4) . ?
C12 C11 1.404(4) . ?
C12 C13 1.372(4) . ?
C7 C8 1.510(4) . ?
C11 C16 1.385(4) . ?
C13 C14 1.377(5) . ?
C17 C18 1.371(5) . ?
C17 C22 1.363(5) . ?
C16 C15 1.380(5) . ?
C2 C3 1.375(5) . ?
C14 C15 1.374(5) . ?
C18 C19 1.360(6) . ?
C3 C4 1.348(6) . ?
C22 C21 1.377(6) . ?
C6 C5 1.371(6) . ?
C4 C5 1.358(6) . ?
C19 C20 1.347(8) . ?
C20 C21 1.352(8) . ?

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
C8 S1 C17 105.79(16) . . ?
C10 N1 C12 112.1(3) . . ?
O1 C10 N1 123.7(3) . . ?
O1 C10 C9 129.6(3) . . ?
N1 C10 C9 106.7(3) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C7 122.0(3) . . ?
C6 C1 C2 117.7(4) . . ?
C11 C9 C10 105.4(3) . . ?
C8 C9 C10 124.8(3) . . ?
C8 C9 C11 129.7(3) . . ?
N1 C12 C11 109.1(3) . . ?
C13 C12 N1 128.4(3) . . ?
C13 C12 C11 122.5(3) . . ?
C8 C7 C1 114.0(3) . . ?
C12 C11 C9 106.7(3) . . ?
C16 C11 C9 135.3(3) . . ?
C16 C11 C12 118.0(3) . . ?
C12 C13 C14 118.0(3) . . ?
C18 C17 S1 120.7(3) . . ?
C22 C17 S1 120.2(3) . . ?
C22 C17 C18 118.9(4) . . ?
C15 C16 C11 119.6(3) . . ?
C9 C8 S1 118.2(3) . . ?
C9 C8 C7 122.9(3) . . ?
C7 C8 S1 118.9(2) . . ?
C3 C2 C1 121.5(4) . . ?
C15 C14 C13 120.8(3) . . ?
C14 C15 C16 121.1(3) . . ?
C19 C18 C17 120.4(5) . . ?
C4 C3 C2 119.6(4) . . ?
C17 C22 C21 120.1(5) . . ?
C1 C6 C5 120.7(4) . . ?
C3 C4 C5 119.9(4) . . ?
C20 C19 C18 120.4(6) . . ?
C19 C20 C21 120.3(5) . . ?
C20 C21 C22 119.9(5) . . ?
C4 C5 C6 120.6(5) . . ?

_olex2_submission_original_sample_id SYTK-SPh-1
_olex2_submission_special_instructions 'No special instructions were received'
