# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_tx2462
_audit_block_doi                 10.5517/ccdc.csd.cc25ny5z
_database_code_depnum_ccdc_archive 'CCDC 2016121'
loop_
_audit_author_name
_audit_author_address
PTZ-QL
;Institution of chemistry
China
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-10-29 downloaded from the CCDC.
;
_audit_creation_date             2020-07-03
_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         'C21 H14 N2 S'
_chemical_formula_sum            'C21 H14 N2 S'
_chemical_formula_weight         326.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNS
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      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                   7.97000(10)
_cell_length_b                   13.74990(10)
_cell_length_c                   14.78660(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.3200(10)
_cell_angle_gamma                90
_cell_volume                     1599.02(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    169.97(13)
_cell_measurement_theta_max      75.3990
_cell_measurement_theta_min      4.4090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11663
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.549
_diffrn_reflns_theta_min         4.418
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.97(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  28.00   0.50    0.05    --  -47.20  26.00 -58.00  110
  2  ω   -121.00 -74.00   0.50    0.05    --  -47.20 -26.00 138.00   94
  3  ω     -4.00  26.00   0.50    0.05    --   47.20 -26.00 138.00   60
  4  ω     37.00  91.00   0.50    0.05    --   47.20  26.00 -58.00  108
  5  ω   -124.00 -99.00   0.50    0.05    --  -99.00 -26.00 138.00   50
  6  ω     95.00 169.00   0.50    0.05    --  103.25  26.00 -58.00  148
  7  ω    -70.00 -41.00   0.50    0.05    --  -47.20 -26.00 138.00   58
  8  ω     20.00  57.00   0.50    0.05    --   47.20-125.00 -60.00   74
  9  ω    -22.00  29.00   0.50    0.05    --   47.20 -19.00   0.00  102
 10  ω     62.00  93.00   0.50    0.05    --   47.20-125.00 -60.00   62
 11  ω    -68.00 -27.00   0.50    0.05    --  -99.00  61.00  30.00   82
 12  ω   -165.00-130.00   0.50    0.05    --  -99.00 -45.00  30.00   70
 13  ω   -129.00-103.00   0.50    0.05    --  -99.00 -45.00  30.00   52
 14  ω    -65.00 -26.00   0.50    0.05    --  -99.00  61.00 120.00   78
 15  ω    -66.00 -40.00   0.50    0.05    --  -99.00  61.00 -60.00   52
 16  ω    -66.00 -26.00   0.50    0.05    --  -99.00  61.00 150.00   80
 17  ω    -84.00 -27.00   0.50    0.05    --  -99.00  77.00  60.00  114
 18  ω    -60.00 -35.00   0.50    0.05    --  -99.00  61.00 -90.00   50
 19  ω    -68.00 -42.00   0.50    0.05    --  -99.00  61.00  90.00   52
 20  ω     32.00  71.00   0.50    0.05    --  103.25 -77.00 -30.00   78
 21  ω     31.00  67.00   0.50    0.05    --  103.25 -61.00-120.00   72
 22  ω     65.00 108.00   0.50    0.05    --  103.25 -77.00  30.00   86
 23  ω     46.00  73.00   0.50    0.05    --  103.25 -61.00 150.00   54
 24  ω    144.00 169.00   0.50    0.05    --  103.25  15.00-150.00   50
 25  ω     90.00 120.00   0.50    0.05    --  103.25  15.00-150.00   60
 26  ω     32.00  75.00   0.50    0.05    --  103.25 -61.00-150.00   86
 27  ω     78.00 109.00   0.50    0.05    --  103.25 -77.00 -30.00   62
 28  ω     31.00  74.00   0.50    0.05    --  103.25 -61.00 -30.00   86
 29  ω     32.00  74.00   0.50    0.05    --  103.25 -61.00-180.00   84
;
_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      0.0065394000
_diffrn_orient_matrix_UB_12      -0.0287331000
_diffrn_orient_matrix_UB_13      0.1012381000
_diffrn_orient_matrix_UB_21      -0.1913485000
_diffrn_orient_matrix_UB_22      -0.0237540000
_diffrn_orient_matrix_UB_23      -0.0190109000
_diffrn_orient_matrix_UB_31      0.0412819000
_diffrn_orient_matrix_UB_32      -0.1056670000
_diffrn_orient_matrix_UB_33      -0.0231596000
_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                3078
_reflns_number_total             3154
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.045
_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)+(0.0424P)²+0.6581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_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 0.45013(4) 0.65456(2) 0.83553(2) 0.02417(10) Uani 1 1 d . . . . .
N1 N 0.55134(12) 0.40057(7) 0.66341(7) 0.0214(2) Uani 1 1 d . . . . .
N2 N 0.36764(13) 0.45766(8) 0.75696(7) 0.0245(2) Uani 1 1 d . . . . .
C1 C 0.39742(15) 0.43193(8) 0.66952(8) 0.0209(2) Uani 1 1 d . . . . .
C2 C 0.26469(15) 0.43879(9) 0.59183(9) 0.0255(3) Uani 1 1 d . . . . .
H2 H 0.158040 0.462662 0.598179 0.031 Uiso 1 1 calc R . . . .
C3 C 0.29784(16) 0.40974(9) 0.50878(9) 0.0258(3) Uani 1 1 d . . . . .
H3 H 0.213032 0.413662 0.457699 0.031 Uiso 1 1 calc R . . . .
C4 C 0.46077(15) 0.37343(9) 0.49915(8) 0.0229(2) Uani 1 1 d . . . . .
C5 C 0.50462(17) 0.34075(9) 0.41557(9) 0.0280(3) Uani 1 1 d . . . . .
H5 H 0.423752 0.341828 0.362630 0.034 Uiso 1 1 calc R . . . .
C6 C 0.66567(18) 0.30738(10) 0.41175(9) 0.0304(3) Uani 1 1 d . . . . .
H6 H 0.693127 0.285364 0.356500 0.037 Uiso 1 1 calc R . . . .
C7 C 0.78906(17) 0.30644(10) 0.49124(9) 0.0293(3) Uani 1 1 d . . . . .
H7 H 0.898437 0.284621 0.488148 0.035 Uiso 1 1 calc R . . . .
C8 C 0.74930(16) 0.33751(9) 0.57344(9) 0.0258(3) Uani 1 1 d . . . . .
H8 H 0.831966 0.336265 0.625614 0.031 Uiso 1 1 calc R . . . .
C9 C 0.58437(15) 0.37133(8) 0.57963(8) 0.0211(2) Uani 1 1 d . . . . .
C10 C 0.22126(15) 0.51302(9) 0.77008(8) 0.0227(2) Uani 1 1 d . . . . .
C11 C 0.05913(16) 0.47301(10) 0.75359(9) 0.0292(3) Uani 1 1 d . . . . .
H11 H 0.044943 0.407922 0.737018 0.035 Uiso 1 1 calc R . . . .
C12 C -0.08169(16) 0.52960(11) 0.76170(10) 0.0327(3) Uani 1 1 d . . . . .
H12 H -0.190369 0.503249 0.748471 0.039 Uiso 1 1 calc R . . . .
C13 C -0.05961(17) 0.62582(11) 0.78968(9) 0.0311(3) Uani 1 1 d . . . . .
H13 H -0.153992 0.664593 0.793088 0.037 Uiso 1 1 calc R . . . .
C14 C 0.10216(16) 0.66427(9) 0.81249(9) 0.0265(3) Uani 1 1 d . . . . .
H14 H 0.116614 0.727687 0.834221 0.032 Uiso 1 1 calc R . . . .
C15 C 0.24324(15) 0.60784(9) 0.80287(8) 0.0214(2) Uani 1 1 d . . . . .
C16 C 0.55455(15) 0.54563(9) 0.87601(8) 0.0218(2) Uani 1 1 d . . . . .
C17 C 0.68739(16) 0.54787(10) 0.95019(8) 0.0260(3) Uani 1 1 d . . . . .
H17 H 0.719726 0.606391 0.979439 0.031 Uiso 1 1 calc R . . . .
C18 C 0.77057(16) 0.46277(10) 0.97994(9) 0.0293(3) Uani 1 1 d . . . . .
H18 H 0.861663 0.464280 1.027970 0.035 Uiso 1 1 calc R . . . .
C19 C 0.71833(17) 0.37494(10) 0.93820(9) 0.0313(3) Uani 1 1 d . . . . .
H19 H 0.773290 0.317648 0.959227 0.038 Uiso 1 1 calc R . . . .
C20 C 0.58498(17) 0.37213(10) 0.86549(9) 0.0285(3) Uani 1 1 d . . . . .
H20 H 0.549038 0.312999 0.838551 0.034 Uiso 1 1 calc R . . . .
C21 C 0.50497(15) 0.45795(9) 0.83289(8) 0.0227(2) 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 C15 1.7626(12) . ?
S1 C16 1.7699(12) . ?
N1 C1 1.3172(15) . ?
N1 C9 1.3680(15) . ?
N2 C1 1.3973(15) . ?
N2 C10 1.4323(15) . ?
N2 C21 1.4354(15) . ?
C1 C2 1.4333(17) . ?
C2 C3 1.3574(18) . ?
C3 C4 1.4197(17) . ?
C4 C5 1.4112(18) . ?
C4 C9 1.4169(16) . ?
C5 C6 1.3728(19) . ?
C6 C7 1.4051(19) . ?
C7 C8 1.3730(18) . ?
C8 C9 1.4112(17) . ?
C10 C11 1.3891(17) . ?
C10 C15 1.3922(17) . ?
C11 C12 1.3867(19) . ?
C12 C13 1.389(2) . ?
C13 C14 1.3837(19) . ?
C14 C15 1.3923(17) . ?
C16 C17 1.3960(17) . ?
C16 C21 1.3909(17) . ?
C17 C18 1.3812(19) . ?
C18 C19 1.389(2) . ?
C19 C20 1.3845(19) . ?
C20 C21 1.3899(18) . ?

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
C15 S1 C16 98.75(6) . . ?
C1 N1 C9 118.44(10) . . ?
C1 N2 C10 121.60(10) . . ?
C1 N2 C21 120.14(10) . . ?
C10 N2 C21 115.29(10) . . ?
N1 C1 N2 116.49(10) . . ?
N1 C1 C2 122.77(11) . . ?
N2 C1 C2 120.73(11) . . ?
C3 C2 C1 118.64(11) . . ?
C2 C3 C4 120.63(11) . . ?
C5 C4 C3 124.06(11) . . ?
C5 C4 C9 119.47(11) . . ?
C9 C4 C3 116.47(11) . . ?
C6 C5 C4 120.54(12) . . ?
C5 C6 C7 120.07(12) . . ?
C8 C7 C6 120.47(12) . . ?
C7 C8 C9 120.72(12) . . ?
N1 C9 C4 123.03(11) . . ?
N1 C9 C8 118.25(11) . . ?
C8 C9 C4 118.72(11) . . ?
C11 C10 N2 121.38(11) . . ?
C11 C10 C15 119.54(11) . . ?
C15 C10 N2 119.05(10) . . ?
C12 C11 C10 120.37(12) . . ?
C11 C12 C13 119.67(12) . . ?
C14 C13 C12 120.31(12) . . ?
C13 C14 C15 119.88(12) . . ?
C10 C15 S1 119.74(9) . . ?
C10 C15 C14 119.95(11) . . ?
C14 C15 S1 120.27(10) . . ?
C17 C16 S1 120.15(10) . . ?
C21 C16 S1 119.69(9) . . ?
C21 C16 C17 120.15(11) . . ?
C18 C17 C16 119.70(12) . . ?
C17 C18 C19 120.08(12) . . ?
C20 C19 C18 120.42(12) . . ?
C19 C20 C21 119.81(12) . . ?
C16 C21 N2 119.01(11) . . ?
C20 C21 N2 121.19(11) . . ?
C20 C21 C16 119.77(11) . . ?

_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 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.824
