# 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_g101105a
_database_code_depnum_ccdc_archive 'CCDC 1977624'
loop_
_audit_author_name
_audit_author_address
MSJI
;Soochow University
China
;
_audit_update_record             
;
2020-01-14 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_audit_creation_date             2020-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H15 N O S'
_chemical_formula_sum            'C21 H15 N O S'
_chemical_formula_weight         329.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.0086(7)
_cell_length_b                   8.6711(5)
_cell_length_c                   21.5443(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.929(7)
_cell_angle_gamma                90.00
_cell_volume                     1652.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3143
_cell_measurement_temperature    294.18(10)
_cell_measurement_theta_max      27.7190
_cell_measurement_theta_min      4.0070
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14216
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_ambient_temperature      294.18(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452  -99.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452  -99.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452    0.0000  -30.0000 124

#__ type_ start__ end____ width___ exp.time_
  4 omega  -13.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452   38.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
  5 omega  -30.00   54.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8077  -95.0000   99.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -91.00   -4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7452  -38.0000  -60.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0070745000
_diffrn_orient_matrix_UB_12      -0.0689267000
_diffrn_orient_matrix_UB_13      0.0169236000
_diffrn_orient_matrix_UB_21      -0.0614346000
_diffrn_orient_matrix_UB_22      0.0325760000
_diffrn_orient_matrix_UB_23      0.0117377000
_diffrn_orient_matrix_UB_31      -0.0510853000
_diffrn_orient_matrix_UB_32      -0.0296278000
_diffrn_orient_matrix_UB_33      -0.0264559000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2511
_reflns_number_total             3380
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.815
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.1216
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1432P)²+7.9667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3118
_refine_ls_wR_factor_ref         0.3322
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 O1, C21
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
 C9, C14
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
 C15, C16
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
 C16, C21
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C5(H5), C12(H12), C13(H13), C14(H14), C11(H11),
 C18(H18), C17(H17), C10(H10), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.17017(17) 0.27608(16) 0.07108(7) 0.0426(5) Uani 1 d . . . .
N1 N 0.0759(6) 0.0842(5) 0.1467(2) 0.0409(11) Uani 1 d . . . .
C0AA C 0.0911(6) 0.2283(6) 0.1363(2) 0.0343(11) Uani 1 d . . . .
C2 C 0.1277(6) -0.0034(6) 0.1010(2) 0.0358(11) Uani 1 d . . . .
C7 C 0.1840(6) 0.0805(6) 0.0555(3) 0.0373(12) Uani 1 d . . . .
O1 O 0.1143(7) 0.4914(5) 0.1627(2) 0.0715(15) Uani 1 d . . . U
C3 C 0.1314(7) -0.1655(7) 0.0994(3) 0.0468(14) Uani 1 d . . . .
H3 H 0.0969 -0.2233 0.1302 0.056 Uiso 1 calc . . R .
C4 C 0.1866(7) -0.2364(7) 0.0519(3) 0.0487(14) Uani 1 d . . . .
H4 H 0.1884 -0.3436 0.0502 0.058 Uiso 1 calc . . R .
C6 C 0.2396(8) 0.0076(7) 0.0074(3) 0.0501(15) Uani 1 d . . . .
H6 H 0.2754 0.0645 -0.0233 0.060 Uiso 1 calc . . R .
C8 C 0.0405(8) 0.3575(6) 0.1750(3) 0.0468(14) Uani 1 d . . . .
C5 C 0.2403(7) -0.1512(7) 0.0062(3) 0.0516(15) Uani 1 d . . . .
H5 H 0.2772 -0.2022 -0.0258 0.062 Uiso 1 calc . . R .
C9 C -0.1361(9) 0.4019(9) 0.1438(4) 0.067(2) Uani 1 d . . . U
C12 C -0.4275(7) 0.4708(8) 0.0909(3) 0.0529(15) Uani 1 d . . . .
H12 H -0.5293 0.4895 0.0750 0.063 Uiso 1 calc . . R .
C13 C -0.3205(9) 0.5491(8) 0.0672(3) 0.0588(18) Uani 1 d . . . .
H13 H -0.3455 0.6212 0.0350 0.071 Uiso 1 calc . . R .
C21 C 0.2554(12) 0.4810(9) 0.2179(3) 0.072(2) Uani 1 d . . . U
C14 C -0.1631(9) 0.5137(9) 0.0954(4) 0.0671(19) Uani 1 d . . . U
H14 H -0.0835 0.5633 0.0818 0.080 Uiso 1 calc . . R .
C15 C 0.0584(9) 0.3196(9) 0.2421(3) 0.0646(18) Uani 1 d . . . U
H15A H 0.0531 0.2096 0.2497 0.078 Uiso 1 calc . . R .
H15B H -0.0125 0.3742 0.2629 0.078 Uiso 1 calc . . R .
C11 C -0.3877(9) 0.3660(9) 0.1373(4) 0.070(2) Uani 1 d . . . .
H11 H -0.4642 0.3161 0.1530 0.084 Uiso 1 calc . . R .
C18 C 0.4653(8) 0.4498(10) 0.3218(4) 0.065(2) Uani 1 d . . . .
H18 H 0.5428 0.4446 0.3571 0.078 Uiso 1 calc . . R .
C17 C 0.3309(12) 0.3613(9) 0.3194(4) 0.080(3) Uani 1 d . . . .
H17 H 0.3149 0.2966 0.3520 0.096 Uiso 1 calc . . R .
C10 C -0.2473(11) 0.3304(12) 0.1614(4) 0.079(3) Uani 1 d . . . .
H10 H -0.2272 0.2527 0.1917 0.095 Uiso 1 calc . . R .
C19 C 0.4791(8) 0.5410(9) 0.2726(4) 0.066(2) Uani 1 d . . . .
H19 H 0.5693 0.5949 0.2752 0.079 Uiso 1 calc . . R .
C16 C 0.2180(8) 0.3825(8) 0.2594(4) 0.0650(18) Uani 1 d . . . U
C20 C 0.3767(10) 0.5602(10) 0.2214(4) 0.073(2) Uani 1 d . . . .
H20 H 0.3910 0.6274 0.1894 0.088 Uiso 1 calc . . R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0584(9) 0.0305(7) 0.0457(8) 0.0017(5) 0.0267(7) -0.0025(6)
N1 0.055(3) 0.028(2) 0.045(3) 0.0016(18) 0.023(2) 0.0005(19)
C0AA 0.040(3) 0.029(2) 0.037(3) 0.003(2) 0.016(2) -0.004(2)
C2 0.038(3) 0.031(3) 0.040(3) 0.000(2) 0.008(2) 0.001(2)
C7 0.039(3) 0.034(3) 0.040(3) -0.002(2) 0.009(2) 0.001(2)
O1 0.129(4) 0.038(2) 0.060(3) 0.000(2) 0.049(3) -0.007(3)
C3 0.055(3) 0.033(3) 0.054(3) 0.001(2) 0.014(3) -0.002(2)
C4 0.056(4) 0.030(3) 0.061(4) -0.009(3) 0.013(3) 0.002(2)
C6 0.064(4) 0.046(3) 0.047(3) -0.004(3) 0.027(3) 0.000(3)
C8 0.072(4) 0.024(3) 0.053(3) 0.001(2) 0.034(3) -0.001(2)
C5 0.053(4) 0.049(4) 0.055(4) -0.013(3) 0.015(3) 0.007(3)
C9 0.061(4) 0.068(4) 0.064(4) -0.026(3) -0.011(4) 0.005(4)
C12 0.041(3) 0.058(4) 0.061(4) -0.010(3) 0.012(3) 0.007(3)
C13 0.087(5) 0.048(4) 0.042(3) -0.003(3) 0.015(3) -0.004(3)
C21 0.120(7) 0.053(4) 0.044(3) -0.013(3) 0.019(3) 0.026(4)
C14 0.062(4) 0.061(4) 0.092(5) -0.028(3) 0.049(4) -0.023(3)
C15 0.075(4) 0.059(4) 0.064(4) -0.002(3) 0.022(4) -0.003(3)
C11 0.078(5) 0.064(5) 0.082(5) 0.013(4) 0.048(4) 0.020(4)
C18 0.057(4) 0.077(5) 0.054(4) -0.015(4) -0.009(3) 0.015(4)
C17 0.128(8) 0.047(4) 0.083(5) 0.015(4) 0.062(5) 0.023(4)
C10 0.089(6) 0.098(6) 0.056(4) 0.014(4) 0.025(4) 0.033(5)
C19 0.055(4) 0.059(4) 0.089(6) -0.020(4) 0.024(4) -0.001(3)
C16 0.053(3) 0.037(3) 0.106(6) -0.021(3) 0.018(4) 0.000(3)
C20 0.076(5) 0.066(5) 0.083(6) -0.008(4) 0.029(5) 0.007(4)

_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 C0AA 1.741(5) . ?
S1 C7 1.738(5) . ?
N1 C0AA 1.281(6) . ?
N1 C2 1.393(7) . ?
C0AA C8 1.518(7) . ?
C2 C7 1.390(8) . ?
C2 C3 1.406(7) . ?
C7 C6 1.387(8) . ?
O1 C8 1.388(7) . ?
O1 C21 1.570(11) . ?
C3 C4 1.365(9) . ?
C4 C5 1.391(9) . ?
C6 C5 1.378(9) . ?
C8 C9 1.651(10) . ?
C8 C15 1.461(9) . ?
C9 C14 1.411(12) . ?
C9 C10 1.294(12) . ?
C12 C13 1.356(10) . ?
C12 C11 1.347(10) . ?
C13 C14 1.465(11) . ?
C21 C16 1.326(12) . ?
C21 C20 1.280(12) . ?
C15 C16 1.517(10) . ?
C11 C10 1.311(11) . ?
C18 C17 1.427(12) . ?
C18 C19 1.348(12) . ?
C17 C16 1.496(12) . ?
C19 C20 1.307(11) . ?

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
C7 S1 C0AA 88.8(3) . . ?
C0AA N1 C2 110.3(4) . . ?
N1 C0AA S1 116.6(4) . . ?
N1 C0AA C8 124.7(5) . . ?
C8 C0AA S1 118.7(4) . . ?
N1 C2 C3 125.1(5) . . ?
C7 C2 N1 115.4(5) . . ?
C7 C2 C3 119.5(5) . . ?
C2 C7 S1 109.0(4) . . ?
C6 C7 S1 129.7(5) . . ?
C6 C7 C2 121.3(5) . . ?
C8 O1 C21 99.0(5) . . ?
C4 C3 C2 118.8(6) . . ?
C3 C4 C5 121.1(5) . . ?
C5 C6 C7 118.3(6) . . ?
C0AA C8 C9 108.4(5) . . ?
O1 C8 C0AA 107.9(4) . . ?
O1 C8 C9 100.8(5) . . ?
O1 C8 C15 114.2(6) . . ?
C15 C8 C0AA 112.9(5) . . ?
C15 C8 C9 111.9(6) . . ?
C6 C5 C4 120.9(6) . . ?
C14 C9 C8 118.6(7) . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 C14 120.8(7) . . ?
C11 C12 C13 120.6(7) . . ?
C12 C13 C14 116.1(6) . . ?
C16 C21 O1 106.0(8) . . ?
C20 C21 O1 125.0(8) . . ?
C20 C21 C16 129.0(9) . . ?
C9 C14 C13 117.9(6) . . ?
C8 C15 C16 94.8(6) . . ?
C10 C11 C12 123.7(8) . . ?
C19 C18 C17 119.4(7) . . ?
C18 C17 C16 113.5(7) . . ?
C9 C10 C11 120.8(8) . . ?
C20 C19 C18 125.7(8) . . ?
C21 C16 C15 114.6(8) . . ?
C21 C16 C17 116.3(7) . . ?
C17 C16 C15 128.7(8) . . ?
C21 C20 C19 116.0(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
