# Electronic Supplementary Material (ESI) for ChemComm.
# 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_f-2
_database_code_depnum_ccdc_archive 'CCDC 2090352'
loop_
_audit_author_name
_audit_author_address
'Yuanyuan Fu'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O S'
_chemical_formula_sum            'C16 H13 N O S'
_chemical_formula_weight         267.33
_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 0.0181 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'

_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   29.5276(11)
_cell_length_b                   29.5276(11)
_cell_length_c                   6.0515(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5276.2(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2500
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      73.1440
_cell_measurement_theta_min      4.2020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4688
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.710
_diffrn_reflns_theta_min         2.993
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     65.00  95.00   1.00    1.01    --   41.11  77.00  90.00   30
  2  ω    129.00 176.00   1.00    1.50    --  106.95 125.00  60.00   47
  3  ω     37.00 133.00   1.00    1.50    --  106.95 -45.00  90.00   96
  4  ω     55.00 109.00   1.00    1.50    --  106.95 -95.00 150.00   54
  5  ω   -111.00 -22.00   1.00    1.01    --  -41.11 -57.00 -30.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0129267000
_diffrn_orient_matrix_UB_12      0.0485193000
_diffrn_orient_matrix_UB_13      0.0681516000
_diffrn_orient_matrix_UB_21      -0.0501569000
_diffrn_orient_matrix_UB_22      -0.0106106000
_diffrn_orient_matrix_UB_23      -0.0484912000
_diffrn_orient_matrix_UB_31      -0.0062523000
_diffrn_orient_matrix_UB_32      -0.0160150000
_diffrn_orient_matrix_UB_33      0.2402949000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2335
_reflns_number_total             2582
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0787P)²+3.3464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1394
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.57510(2) 0.53068(2) 0.34953(8) 0.02133(19) Uani 1 1 d . . . . .
O1 O 0.70538(5) 0.43298(5) 0.6351(2) 0.0211(3) Uani 1 1 d . . . . .
N1 N 0.68090(6) 0.49764(6) 0.3054(3) 0.0207(4) Uani 1 1 d . . . . .
H1A H 0.700581 0.476683 0.281234 0.025 Uiso 1 1 d R U . . .
H1B H 0.6691(9) 0.5123(10) 0.197(5) 0.033(7) Uiso 1 1 d . . . . .
C1 C 0.62986(7) 0.44396(7) 0.7916(3) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.59397(7) 0.47164(6) 0.7188(3) 0.0189(4) Uani 1 1 d . . . . .
C3 C 0.55339(7) 0.47128(7) 0.8301(3) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.529306 0.489160 0.783293 0.028 Uiso 1 1 calc R U . . .
C4 C 0.54924(7) 0.44312(7) 1.0167(4) 0.0255(5) Uani 1 1 d . . . . .
H4 H 0.521999 0.442604 1.093755 0.031 Uiso 1 1 calc R U . . .
C5 C 0.58470(8) 0.41618(7) 1.0884(3) 0.0265(5) Uani 1 1 d . . . . .
H5 H 0.581181 0.398037 1.212880 0.032 Uiso 1 1 calc R U . . .
C6 C 0.62594(7) 0.41628(7) 0.9732(3) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.649952 0.398122 1.018445 0.028 Uiso 1 1 calc R U . . .
C7 C 0.66799(7) 0.45064(6) 0.6356(3) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.65185(7) 0.48405(6) 0.4664(3) 0.0171(4) Uani 1 1 d . . . . .
C9 C 0.60884(6) 0.49666(6) 0.5174(3) 0.0181(4) Uani 1 1 d . . . . .
C10 C 0.55747(6) 0.57562(6) 0.5237(3) 0.0182(4) Uani 1 1 d . . . . .
C11 C 0.52116(7) 0.60163(7) 0.4467(3) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.508229 0.595198 0.310089 0.026 Uiso 1 1 calc R U . . .
C12 C 0.50441(7) 0.63692(7) 0.5732(3) 0.0228(4) Uani 1 1 d . . . . .
H12 H 0.480467 0.654191 0.519685 0.027 Uiso 1 1 calc R U . . .
C13 C 0.52283(7) 0.64701(7) 0.7796(3) 0.0228(4) Uani 1 1 d . . . . .
C14 C 0.55949(7) 0.62155(7) 0.8515(3) 0.0239(4) Uani 1 1 d . . . . .
H14 H 0.572712 0.628400 0.986956 0.029 Uiso 1 1 calc R U . . .
C15 C 0.57705(7) 0.58599(7) 0.7265(3) 0.0224(4) Uani 1 1 d . . . . .
H15 H 0.601609 0.569371 0.778238 0.027 Uiso 1 1 calc R U . . .
C16 C 0.50216(8) 0.68336(8) 0.9218(4) 0.0332(5) Uani 1 1 d . . . . .
H16A H 0.520978 0.709865 0.918056 0.050 Uiso 1 1 calc R U . . .
H16B H 0.499754 0.672656 1.071095 0.050 Uiso 1 1 calc R U . . .
H16C H 0.472568 0.690757 0.866859 0.050 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 C9 1.7416(19) . ?
S1 C10 1.7729(19) . ?
O1 C7 1.221(2) . ?
N1 H1A 0.8614 . ?
N1 H1B 0.86(3) . ?
N1 C8 1.359(2) . ?
C1 C2 1.409(3) . ?
C1 C6 1.374(3) . ?
C1 C7 1.483(3) . ?
C2 C3 1.374(3) . ?
C2 C9 1.491(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.408(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.499(3) . ?
C8 C9 1.359(3) . ?
C10 C11 1.399(3) . ?
C10 C15 1.391(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(3) . ?
C13 C14 1.388(3) . ?
C13 C16 1.505(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C9 S1 C10 104.65(9) . . ?
H1A N1 H1B 120.4 . . ?
C8 N1 H1A 109.6 . . ?
C8 N1 H1B 116.1(19) . . ?
C2 C1 C7 107.15(16) . . ?
C6 C1 C2 122.12(19) . . ?
C6 C1 C7 130.71(19) . . ?
C1 C2 C9 108.75(17) . . ?
C3 C2 C1 119.87(19) . . ?
C3 C2 C9 131.36(19) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.3(2) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.67(19) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
O1 C7 C1 129.15(18) . . ?
O1 C7 C8 124.52(17) . . ?
C1 C7 C8 106.32(16) . . ?
N1 C8 C7 118.90(17) . . ?
N1 C8 C9 132.21(18) . . ?
C9 C8 C7 108.80(16) . . ?
C2 C9 S1 126.45(14) . . ?
C8 C9 S1 124.07(15) . . ?
C8 C9 C2 108.96(17) . . ?
C11 C10 S1 115.96(14) . . ?
C15 C10 S1 124.58(15) . . ?
C15 C10 C11 119.46(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.17(18) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.13(19) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C16 120.42(19) . . ?
C14 C13 C12 118.00(18) . . ?
C14 C13 C16 121.54(19) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.85(19) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 C14 119.36(18) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
S1 C10 C11 C12 178.72(16) . . . . ?
S1 C10 C15 C14 -178.42(16) . . . . ?
O1 C7 C8 N1 -3.0(3) . . . . ?
O1 C7 C8 C9 179.98(18) . . . . ?
N1 C8 C9 S1 10.2(3) . . . . ?
N1 C8 C9 C2 -177.66(19) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C2 C9 S1 173.07(14) . . . . ?
C1 C2 C9 C8 1.2(2) . . . . ?
C1 C7 C8 N1 177.84(16) . . . . ?
C1 C7 C8 C9 0.9(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C7 O1 -179.18(19) . . . . ?
C2 C1 C7 C8 -0.1(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C2 C9 S1 -5.5(3) . . . . ?
C3 C2 C9 C8 -177.4(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C1 C2 C9 -179.08(17) . . . . ?
C6 C1 C7 O1 -0.9(4) . . . . ?
C6 C1 C7 C8 178.2(2) . . . . ?
C7 C1 C2 C3 178.15(17) . . . . ?
C7 C1 C2 C9 -0.6(2) . . . . ?
C7 C1 C6 C5 -178.39(19) . . . . ?
C7 C8 C9 S1 -173.36(13) . . . . ?
C7 C8 C9 C2 -1.2(2) . . . . ?
C9 S1 C10 C11 -164.63(15) . . . . ?
C9 S1 C10 C15 15.1(2) . . . . ?
C9 C2 C3 C4 178.98(19) . . . . ?
C10 S1 C9 C2 63.12(18) . . . . ?
C10 S1 C9 C8 -126.15(17) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C10 C15 C14 1.3(3) . . . . ?
C11 C12 C13 C14 2.1(3) . . . . ?
C11 C12 C13 C16 -175.7(2) . . . . ?
C12 C13 C14 C15 -1.8(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C15 C10 C11 C12 -1.1(3) . . . . ?
C16 C13 C14 C15 176.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.585
