# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_tx101
_database_code_depnum_ccdc_archive 'CCDC 1955137'
loop_
_audit_author_name
_audit_author_address
'Zuo Xiao'
;National Center for Nanoscience and Technology
China
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2020-04-12 downloaded from the CCDC.
;
_audit_creation_date             2018-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H6 N2 O S'
_chemical_formula_sum            'C14 H6 N2 O S'
_chemical_formula_weight         250.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOS
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.38200(10)
_cell_length_b                   21.4301(4)
_cell_length_c                   7.7843(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.060(2)
_cell_angle_gamma                90
_cell_volume                     1124.46(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7944
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      75.3510
_cell_measurement_theta_min      4.1280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10503
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.783
_diffrn_reflns_theta_min         4.126
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  95.00   0.50    1.00    --   47.32-125.00 -81.00  158
  2  ω     68.00 120.00   0.50    2.00    --  103.25 -61.00 -90.00  104
  3  ω     31.00 117.00   0.50    2.00    --  103.25-125.00 -81.00  172
  4  ω     31.00 116.00   0.50    2.00    --  103.25-125.00-180.00  170
  5  ω     28.00 107.00   0.50    1.00    --   47.32-147.00 113.00  158
  6  ω     31.00 123.00   0.50    2.00    --  103.25-147.00 113.00  184
  7  ω     88.00 167.00   0.50    2.00    --  103.25  61.00  90.00  158
  8  ω    114.00 166.00   0.50    2.00    --  103.25 147.00 162.00  104
  9  ω     81.00 168.00   0.50    2.00    --  103.25  77.00  60.00  174
 10  ω     62.00 119.00   0.50    1.00    --   47.32 147.00 162.00  114
 11  ω     63.00 109.00   0.50    2.00    --  103.25 147.00 162.00   92
 12  ω    -77.00 -52.00   0.50    1.00    --  -47.32 125.00  -2.00   50
 13  ω   -117.00 -26.00   0.50    2.00    --  -99.00 125.00  -2.00  182
 14  ω    -66.00 -41.00   0.50    2.00    --  -99.00  45.00-150.00   50
 15  ω    -92.00 -43.00   0.50    2.00    --  -99.00  61.00-150.00   98
 16  ω    -96.00 -67.00   0.50    2.00    --  -99.00  45.00-150.00   58
 17  ω   -117.00 -36.00   0.50    1.00    --  -47.32 -38.00-180.00  162
 18  ω   -119.00 -71.00   0.50    1.00    --  -47.32-125.00 -81.00   96
 19  ω   -119.00 -56.00   0.50    1.00    --  -47.32-147.00 113.00  126
 20  ω   -118.00 -51.00   0.50    1.00    --  -47.32 -77.00 -60.00  134
 21  ω   -168.00 -56.00   0.50    2.00    --  -99.00-147.00 113.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1481162000
_diffrn_orient_matrix_UB_12      0.0528565000
_diffrn_orient_matrix_UB_13      -0.0183366000
_diffrn_orient_matrix_UB_21      -0.1671706000
_diffrn_orient_matrix_UB_22      -0.0484257000
_diffrn_orient_matrix_UB_23      -0.0432172000
_diffrn_orient_matrix_UB_31      0.0483381000
_diffrn_orient_matrix_UB_32      -0.0053626000
_diffrn_orient_matrix_UB_33      0.2115742000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2148
_reflns_number_total             2216
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.075
_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)+(0.0617P)²+0.4459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
;
_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 0.76731(5) 0.51987(2) 0.76329(4) 0.01960(14) Uani 1 1 d . . . . .
O1 O 0.72863(17) 0.47879(5) 0.11903(15) 0.0279(3) Uani 1 1 d . . . . .
N1 N 0.6806(2) 0.66878(6) 0.82374(19) 0.0349(3) Uani 1 1 d . . . . .
N2 N 0.5866(3) 0.75034(7) 0.2695(2) 0.0435(4) Uani 1 1 d . . . . .
C1 C 0.73370(19) 0.53962(6) 0.53752(19) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.7516(2) 0.48992(6) 0.43410(19) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.7946(2) 0.43223(6) 0.53448(19) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.80814(19) 0.44180(6) 0.71952(19) 0.0197(3) Uani 1 1 d . . . . .
C5 C 0.8519(2) 0.39232(6) 0.84723(19) 0.0226(3) Uani 1 1 d . . . . .
H5 H 0.862281 0.398477 0.969163 0.027 Uiso 1 1 calc R . . . .
C6 C 0.8792(2) 0.33403(7) 0.7861(2) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.909231 0.300581 0.869275 0.031 Uiso 1 1 calc R . . . .
C7 C 0.8630(2) 0.32368(7) 0.6027(2) 0.0257(3) Uani 1 1 d . . . . .
H7 H 0.880404 0.283650 0.565758 0.031 Uiso 1 1 calc R . . . .
C8 C 0.8215(2) 0.37237(6) 0.4763(2) 0.0226(3) Uani 1 1 d . . . . .
H8 H 0.811602 0.365575 0.354817 0.027 Uiso 1 1 calc R . . . .
C9 C 0.7203(2) 0.51092(7) 0.24442(19) 0.0207(3) Uani 1 1 d . . . . .
C10 C 0.6749(2) 0.58061(6) 0.23449(19) 0.0221(3) Uani 1 1 d . . . . .
H10A H 0.770890 0.604213 0.205330 0.027 Uiso 1 1 calc R . . . .
H10B H 0.543076 0.589215 0.139469 0.027 Uiso 1 1 calc R . . . .
C11 C 0.6886(2) 0.59684(6) 0.42868(19) 0.0200(3) Uani 1 1 d . . . . .
C12 C 0.6627(2) 0.65422(6) 0.4877(2) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.6206(2) 0.70761(7) 0.3657(2) 0.0289(3) Uani 1 1 d . . . . .
C14 C 0.6735(2) 0.66360(6) 0.6743(2) 0.0252(3) Uani 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
S1 C1 1.7245(14) . ?
S1 C4 1.7576(14) . ?
O1 C9 1.2165(17) . ?
N1 C14 1.148(2) . ?
N2 C13 1.144(2) . ?
C1 C2 1.3737(19) . ?
C1 C11 1.4498(18) . ?
C2 C3 1.4274(18) . ?
C2 C9 1.4689(19) . ?
C3 C4 1.4175(19) . ?
C3 C8 1.4013(19) . ?
C4 C5 1.3983(19) . ?
C5 C6 1.381(2) . ?
C6 C7 1.401(2) . ?
C7 C8 1.380(2) . ?
C9 C10 1.526(2) . ?
C10 C11 1.5136(19) . ?
C11 C12 1.3532(19) . ?
C12 C13 1.438(2) . ?
C12 C14 1.437(2) . ?

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
C1 S1 C4 90.05(6) . . ?
C2 C1 S1 113.49(11) . . ?
C2 C1 C11 111.55(12) . . ?
C11 C1 S1 134.96(11) . . ?
C1 C2 C3 113.82(13) . . ?
C1 C2 C9 109.76(12) . . ?
C3 C2 C9 136.42(13) . . ?
C4 C3 C2 109.80(12) . . ?
C8 C3 C2 130.18(13) . . ?
C8 C3 C4 120.01(12) . . ?
C3 C4 S1 112.84(10) . . ?
C5 C4 S1 126.31(11) . . ?
C5 C4 C3 120.85(12) . . ?
C6 C5 C4 117.72(13) . . ?
C5 C6 C7 122.05(13) . . ?
C8 C7 C6 120.56(13) . . ?
C7 C8 C3 118.79(13) . . ?
O1 C9 C2 126.47(13) . . ?
O1 C9 C10 126.54(13) . . ?
C2 C9 C10 106.99(11) . . ?
C11 C10 C9 104.50(11) . . ?
C1 C11 C10 107.18(11) . . ?
C12 C11 C1 126.92(13) . . ?
C12 C11 C10 125.90(12) . . ?
C11 C12 C13 121.44(13) . . ?
C11 C12 C14 120.87(13) . . ?
C14 C12 C13 117.68(12) . . ?
N2 C13 C12 179.45(18) . . ?
N1 C14 C12 177.45(15) . . ?

_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 1.894
_oxdiff_exptl_absorpt_empirical_full_min 0.364
