# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_exp_372
_database_code_depnum_ccdc_archive 'CCDC 2033809'
loop_
_audit_author_name
_audit_author_address
'Si Liu'
;Tianjin University
China
;
_audit_update_record             
;
2020-09-24 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_audit_creation_date             2020-08-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 N S'
_chemical_formula_sum            'C17 H11 N S'
_chemical_formula_weight         261.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H11NS
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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   24.3454(3)
_cell_length_b                   8.44650(10)
_cell_length_c                   6.09350(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1253.03(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8710
_cell_measurement_theta_min      5.5210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7392
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.032
_diffrn_reflns_theta_max         67.032
_diffrn_reflns_theta_min         3.631
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -20.00   1.00    3.75    --  -41.12 -57.00   0.00   91
  2  ω    -69.00  27.00   1.00    3.75    --  -41.12  57.00 150.00   96
  3  ω     54.00 101.00   1.00    3.75    --   41.12-139.00 -10.00   47
  4  ω    -32.00  65.00   1.00    3.75    --   41.12 -37.00-150.00   97
  5  ω     36.00  73.00   1.00   15.50    --  105.32 -61.00 -30.00   37
  6  ω    107.00 168.00   1.00   15.50    --  105.32  77.00 -90.00   61
  7  ω     49.00 115.00   1.00   15.50    --  105.32 -77.00 120.00   66
  8  ω     37.00 124.00   1.00   15.50    --  105.32 -45.00 120.00   87
  9  ω     47.00 130.00   1.00   15.50    --  105.32 -45.00-150.00   83
 10  ω     24.00 108.00   1.00   15.50    --  105.32 -94.00  60.00   84
 11  ω     61.00 111.00   1.00   15.50    --  105.32 -45.00   0.00   50
 12  ω     72.00 114.00   1.00   15.50    --  105.32-125.00 -60.00   42
 13  ω     51.00 104.00   1.00   15.50    --  105.32 -94.00 -30.00   53
 14  ω     19.00 171.00   1.00   15.50    --  105.32   0.00 -90.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0593820000
_diffrn_orient_matrix_UB_12      -0.0255171000
_diffrn_orient_matrix_UB_13      0.0802715000
_diffrn_orient_matrix_UB_21      0.0218681000
_diffrn_orient_matrix_UB_22      0.0549070000
_diffrn_orient_matrix_UB_23      -0.2246748000
_diffrn_orient_matrix_UB_31      0.0018241000
_diffrn_orient_matrix_UB_32      0.1719593000
_diffrn_orient_matrix_UB_33      0.0836652000
_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         0.808
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2178
_reflns_number_total             2231
_reflns_odcompleteness_completeness 99.93
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.075
_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)+(0.0439P)²+0.0721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0698
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
S001 S 0.28034(2) 0.29669(7) 0.57520(13) 0.0555(2) Uani 1 1 d . . . . .
N002 N 0.29388(9) 0.4672(3) 0.2327(4) 0.0547(5) Uani 1 1 d . . . . .
C003 C 0.54698(8) 0.7982(2) 0.6125(4) 0.0385(5) Uani 1 1 d . . . . .
C004 C 0.46343(9) 0.6475(2) 0.6762(3) 0.0371(4) Uani 1 1 d . . . . .
C005 C 0.51426(9) 0.7033(2) 0.7466(4) 0.0395(5) Uani 1 1 d . . . . .
C006 C 0.43031(10) 0.5458(3) 0.8083(4) 0.0428(5) Uani 1 1 d . . . . .
C007 C 0.44370(9) 0.6894(2) 0.4612(3) 0.0355(4) Uani 1 1 d . . . . .
C008 C 0.38254(10) 0.4850(3) 0.7317(4) 0.0442(5) Uani 1 1 d . . . . .
C009 C 0.47602(9) 0.7869(2) 0.3290(4) 0.0371(4) Uani 1 1 d . . . . .
C00A C 0.36320(9) 0.5221(2) 0.5163(4) 0.0396(5) Uani 1 1 d . . . . .
C00B C 0.39265(8) 0.6252(3) 0.3880(4) 0.0389(5) Uani 1 1 d . . . . .
C00C C 0.52728(8) 0.8412(2) 0.3990(4) 0.0372(4) Uani 1 1 d . . . . .
C00D C 0.31406(9) 0.4441(3) 0.4284(4) 0.0429(5) Uani 1 1 d . . . . .
C00E C 0.60009(10) 0.8526(3) 0.6795(4) 0.0479(5) Uani 1 1 d . . . . .
C00F C 0.56103(9) 0.9378(3) 0.2632(4) 0.0450(5) Uani 1 1 d . . . . .
C00G C 0.63110(10) 0.9434(3) 0.5434(5) 0.0570(7) Uani 1 1 d . . . . .
C00H C 0.61147(11) 0.9870(3) 0.3333(5) 0.0553(6) Uani 1 1 d . . . . .
C00I C 0.25055(11) 0.3670(4) 0.1943(5) 0.0611(7) Uani 1 1 d . . . . .
C00J C 0.23741(11) 0.2681(3) 0.3580(5) 0.0589(7) Uani 1 1 d . . . . .
H005 H 0.5263(10) 0.678(3) 0.883(5) 0.037(6) Uiso 1 1 d . . . . .
H00B H 0.3801(10) 0.646(3) 0.236(4) 0.039(6) Uiso 1 1 d . . . . .
H00G H 0.6685(15) 0.977(4) 0.584(7) 0.079(9) Uiso 1 1 d . . . . .
H009 H 0.4618(10) 0.812(3) 0.182(5) 0.039(6) Uiso 1 1 d . . . . .
H00F H 0.5486(12) 0.962(3) 0.117(6) 0.060(8) Uiso 1 1 d . . . . .
H008 H 0.3630(12) 0.419(3) 0.824(5) 0.054(8) Uiso 1 1 d . . . . .
H006 H 0.4411(11) 0.521(3) 0.954(5) 0.042(6) Uiso 1 1 d . . . . .
H00E H 0.6112(11) 0.827(3) 0.817(6) 0.050(7) Uiso 1 1 d . . . . .
H00H H 0.6350(14) 1.053(4) 0.236(6) 0.077(10) Uiso 1 1 d . . . . .
H00J H 0.2118(14) 0.198(4) 0.363(6) 0.071(10) Uiso 1 1 d . . . . .
H00I H 0.2343(16) 0.373(4) 0.055(8) 0.088(11) Uiso 1 1 d . . . . .


_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
S001 C00D 1.739(2) . ?
S001 C00J 1.704(3) . ?
N002 C00D 1.304(3) . ?
N002 C00I 1.372(4) . ?
C003 C005 1.395(3) . ?
C003 C00C 1.433(3) . ?
C003 C00E 1.431(3) . ?
C004 C005 1.392(3) . ?
C004 C006 1.427(3) . ?
C004 C007 1.439(3) . ?
C005 H005 0.91(3) . ?
C006 C008 1.354(4) . ?
C006 H006 0.95(3) . ?
C007 C009 1.395(3) . ?
C007 C00B 1.427(3) . ?
C008 C00A 1.430(3) . ?
C008 H008 0.92(3) . ?
C009 C00C 1.396(3) . ?
C009 H009 0.99(3) . ?
C00A C00B 1.373(3) . ?
C00A C00D 1.467(3) . ?
C00B H00B 0.99(3) . ?
C00C C00F 1.424(3) . ?
C00E C00G 1.359(4) . ?
C00E H00E 0.90(3) . ?
C00F C00H 1.365(4) . ?
C00F H00F 0.96(4) . ?
C00G C00H 1.415(4) . ?
C00G H00G 0.98(4) . ?
C00H H00H 0.99(4) . ?
C00I C00J 1.340(4) . ?
C00I H00I 0.94(5) . ?
C00J H00J 0.86(3) . ?

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
C00J S001 C00D 89.52(13) . . ?
C00D N002 C00I 110.7(2) . . ?
C005 C003 C00C 119.09(19) . . ?
C005 C003 C00E 122.2(2) . . ?
C00E C003 C00C 118.7(2) . . ?
C005 C004 C006 122.2(2) . . ?
C005 C004 C007 119.6(2) . . ?
C006 C004 C007 118.2(2) . . ?
C003 C005 H005 119.3(15) . . ?
C004 C005 C003 121.5(2) . . ?
C004 C005 H005 119.3(15) . . ?
C004 C006 H006 120.1(16) . . ?
C008 C006 C004 121.3(2) . . ?
C008 C006 H006 118.6(16) . . ?
C009 C007 C004 118.8(2) . . ?
C009 C007 C00B 122.3(2) . . ?
C00B C007 C004 118.8(2) . . ?
C006 C008 C00A 121.1(2) . . ?
C006 C008 H008 117.6(18) . . ?
C00A C008 H008 121.4(18) . . ?
C007 C009 C00C 121.4(2) . . ?
C007 C009 H009 117.1(14) . . ?
C00C C009 H009 121.4(14) . . ?
C008 C00A C00D 120.3(2) . . ?
C00B C00A C008 119.4(2) . . ?
C00B C00A C00D 120.2(2) . . ?
C007 C00B H00B 119.6(15) . . ?
C00A C00B C007 121.2(2) . . ?
C00A C00B H00B 118.8(15) . . ?
C009 C00C C003 119.6(2) . . ?
C009 C00C C00F 121.8(2) . . ?
C00F C00C C003 118.7(2) . . ?
N002 C00D S001 113.53(18) . . ?
N002 C00D C00A 125.0(2) . . ?
C00A C00D S001 121.25(17) . . ?
C003 C00E H00E 117.2(18) . . ?
C00G C00E C003 120.6(2) . . ?
C00G C00E H00E 122.2(18) . . ?
C00C C00F H00F 118.5(18) . . ?
C00H C00F C00C 120.8(2) . . ?
C00H C00F H00F 120.6(17) . . ?
C00E C00G C00H 120.8(2) . . ?
C00E C00G H00G 122(2) . . ?
C00H C00G H00G 118(3) . . ?
C00F C00H C00G 120.5(2) . . ?
C00F C00H H00H 120(2) . . ?
C00G C00H H00H 119(2) . . ?
N002 C00I H00I 116(2) . . ?
C00J C00I N002 116.2(3) . . ?
C00J C00I H00I 127(2) . . ?
S001 C00J H00J 121(3) . . ?
C00I C00J S001 110.1(2) . . ?
C00I C00J H00J 129(3) . . ?

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
N002 C00I C00J S001 -0.1(4) . . . . ?
C003 C00C C00F C00H 0.9(3) . . . . ?
C003 C00E C00G C00H 0.4(4) . . . . ?
C004 C006 C008 C00A -0.8(3) . . . . ?
C004 C007 C009 C00C 1.5(3) . . . . ?
C004 C007 C00B C00A -1.7(3) . . . . ?
C005 C003 C00C C009 -0.3(3) . . . . ?
C005 C003 C00C C00F -179.86(19) . . . . ?
C005 C003 C00E C00G 179.2(2) . . . . ?
C005 C004 C006 C008 -175.9(2) . . . . ?
C005 C004 C007 C009 -0.7(3) . . . . ?
C005 C004 C007 C00B 177.17(18) . . . . ?
C006 C004 C005 C003 177.77(18) . . . . ?
C006 C004 C007 C009 -179.08(19) . . . . ?
C006 C004 C007 C00B -1.2(3) . . . . ?
C006 C008 C00A C00B -2.1(3) . . . . ?
C006 C008 C00A C00D 174.4(2) . . . . ?
C007 C004 C005 C003 -0.6(3) . . . . ?
C007 C004 C006 C008 2.4(3) . . . . ?
C007 C009 C00C C003 -1.0(3) . . . . ?
C007 C009 C00C C00F 178.6(2) . . . . ?
C008 C00A C00B C007 3.4(3) . . . . ?
C008 C00A C00D S001 -3.8(3) . . . . ?
C008 C00A C00D N002 -178.4(2) . . . . ?
C009 C007 C00B C00A 176.10(19) . . . . ?
C009 C00C C00F C00H -178.7(2) . . . . ?
C00B C007 C009 C00C -176.31(19) . . . . ?
C00B C00A C00D S001 172.71(16) . . . . ?
C00B C00A C00D N002 -1.9(3) . . . . ?
C00C C003 C005 C004 1.0(3) . . . . ?
C00C C003 C00E C00G 0.2(3) . . . . ?
C00C C00F C00H C00G -0.3(4) . . . . ?
C00D S001 C00J C00I 0.1(2) . . . . ?
C00D N002 C00I C00J 0.1(4) . . . . ?
C00D C00A C00B C007 -173.22(19) . . . . ?
C00E C003 C005 C004 -178.01(19) . . . . ?
C00E C003 C00C C009 178.82(19) . . . . ?
C00E C003 C00C C00F -0.8(3) . . . . ?
C00E C00G C00H C00F -0.3(4) . . . . ?
C00I N002 C00D S001 0.0(3) . . . . ?
C00I N002 C00D C00A 175.0(2) . . . . ?
C00J S001 C00D N002 -0.10(19) . . . . ?
C00J S001 C00D C00A -175.25(19) . . . . ?

_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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.840
