# 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_c1-4
_database_code_depnum_ccdc_archive 'CCDC 2015132'
loop_
_audit_author_name
_audit_author_address
'Huajie Chen'
;Xiangtan University
China
;
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-04-18
_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         '2(C13 H12 N3 S2)'
_chemical_formula_sum            'C26 H24 N6 S4'
_chemical_formula_weight         548.75
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7842(8)
_cell_length_b                   9.3195(13)
_cell_length_c                   17.744(2)
_cell_angle_alpha                98.352(12)
_cell_angle_beta                 101.629(10)
_cell_angle_gamma                94.886(10)
_cell_volume                     1238.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1759
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9390
_cell_measurement_theta_min      5.0980
_shelx_estimated_absorpt_T_max   0.753
_shelx_estimated_absorpt_T_min   0.661
_exptl_absorpt_coefficient_mu    3.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36812
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.12
_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  0.0990
_diffrn_reflns_av_unetI/netI     0.1194
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7627
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.011
_diffrn_reflns_theta_min         2.578
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  28.00   1.00    2.00    --  -40.73  57.00  30.00   95
  2  ω    -49.00  32.00   1.00    2.00    --  -40.73  38.00-180.00   81
  3  ω      1.00  42.00   1.00    2.00    --   40.73 -99.00  90.00   41
  4  ω     30.00 108.00   1.00    4.00    --  106.95 -94.00  30.00   78
  5  ω    103.00 140.00   1.00    4.00    --  106.95 -77.00  60.00   37
  6  ω     96.00 135.00   1.00    4.00    --  106.95 -30.00 -30.00   39
  7  ω    108.00 136.00   1.00    4.00    --  106.95  15.00   0.00   28
  8  ω     90.00 137.00   1.00    4.00    --  106.95 -77.00 120.00   47
  9  ω     65.00 126.00   1.00    4.00    --  106.95 -30.00 150.00   61
 10  ω     83.00 174.00   1.00    4.00    --  106.95  45.00 150.00   91
 11  ω    102.00 166.00   1.00    4.00    --  106.95 125.00  90.00   64
 12  ω     64.00  91.00   1.00    4.00    --  106.95  15.00   0.00   27
 13  ω     41.00  80.00   1.00    4.00    --  106.95 -30.00 -30.00   39
 14  ω     40.00  71.00   1.00    4.00    --  106.95 -77.00  60.00   31
 15  ω     39.00 106.00   1.00    4.00    --  106.95 -94.00 120.00   67
 16  ω     44.00 117.00   1.00    4.00    --  106.95-125.00 -30.00   73
 17  ω     42.00  88.00   1.00    2.00    --   40.73-125.00-150.00   46
 18  ω     82.00 177.00   1.00    4.00    --  106.95  45.00-150.00   95
 19  ω   -113.00 -18.00   1.00    6.00    --  -40.73 -57.00-120.00   95
;
_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      0.1808793000
_diffrn_orient_matrix_UB_12      -0.0322982000
_diffrn_orient_matrix_UB_13      -0.0165927000
_diffrn_orient_matrix_UB_21      -0.0712888000
_diffrn_orient_matrix_UB_22      0.0004026000
_diffrn_orient_matrix_UB_23      -0.0875008000
_diffrn_orient_matrix_UB_31      0.0600407000
_diffrn_orient_matrix_UB_32      0.1651250000
_diffrn_orient_matrix_UB_33      0.0122124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                3461
_reflns_number_total             4750
_reflns_odcompleteness_completeness 99.23
_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 (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         1.138
_refine_diff_density_min         -0.950
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0893
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+30.7423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1802
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10B(H10C,H10D), C11(H11A,H11B), C10(H10A,H10B), C12B(H12C,H12D), C12(H12A,
 H12B), C11B(H11C,H11D)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C9B(H9B), C3B(H3B), C2B(H2B)
2.c Idealised Me refined as rotating group:
 C13B(H13D,H13E,H13F), C13(H13A,H13B,H13C)
;
_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 0.07271(17) 0.30217(17) 0.07410(9) 0.0239(4) Uani 1 1 d . . . . .
S10B S 0.96777(18) 0.88717(17) 0.12964(9) 0.0241(3) Uani 1 1 d . . . . .
S2 S 0.81782(18) 0.17399(16) 0.24730(9) 0.0218(3) Uani 1 1 d . . . . .
S11B S 0.27668(18) 0.62796(16) 0.21964(9) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.2303(6) 0.2460(6) 0.1320(3) 0.0227(12) Uani 1 1 d . . . . .
N2 N 0.1825(6) 0.3981(6) 0.0261(3) 0.0235(12) Uani 1 1 d . . . . .
N12B N 0.8285(6) 0.7995(5) 0.1683(3) 0.0200(12) Uani 1 1 d . . . . .
N11B N 0.8363(6) 0.9589(6) 0.0674(3) 0.0243(13) Uani 1 1 d . . . . .
N10B N 0.3536(6) 0.8076(5) 0.1079(3) 0.0213(12) Uani 1 1 d . . . . .
N1 N 0.6925(6) 0.3441(6) 0.1305(3) 0.0245(13) Uani 1 1 d . . . . .
C5B C 0.5027(7) 0.7740(6) 0.1485(3) 0.0189(13) Uani 1 1 d . . . . .
C7B C 0.6692(7) 0.9194(6) 0.0745(3) 0.0177(13) Uani 1 1 d . . . . .
C10B C 0.2399(8) 0.4358(7) 0.3255(4) 0.0256(15) Uani 1 1 d . . . . .
H10C H 0.309231 0.400928 0.369574 0.031 Uiso 1 1 calc R . . . .
H10D H 0.188426 0.351347 0.286215 0.031 Uiso 1 1 calc R . . . .
C6B C 0.6667(7) 0.8262(6) 0.1326(3) 0.0182(13) Uani 1 1 d . . . . .
C11 C 1.0623(8) 0.1112(6) 0.4074(4) 0.0217(14) Uani 1 1 d . . . . .
H11A H 1.102125 0.173978 0.373705 0.026 Uiso 1 1 calc R . . . .
H11B H 1.014945 0.171446 0.445807 0.026 Uiso 1 1 calc R . . . .
C10 C 0.9151(8) -0.0035(7) 0.3585(4) 0.0249(15) Uani 1 1 d . . . . .
H10A H 0.965349 -0.070085 0.323916 0.030 Uiso 1 1 calc R . . . .
H10B H 0.867047 -0.059640 0.392970 0.030 Uiso 1 1 calc R . . . .
C7 C 0.5052(7) 0.4545(5) 0.0312(3) 0.0170(13) Uani 1 1 d . . . . .
C12B C 0.1501(8) 0.6400(7) 0.4216(4) 0.0272(15) Uani 1 1 d . . . . .
H12C H 0.231452 0.711448 0.407934 0.033 Uiso 1 1 calc R . . . .
H12D H 0.047993 0.687189 0.430650 0.033 Uiso 1 1 calc R . . . .
C8B C 0.5066(7) 0.9534(6) 0.0306(3) 0.0177(13) Uani 1 1 d . . . . .
C1 C 0.5976(7) 0.1922(6) 0.2136(4) 0.0215(14) Uani 1 1 d . . . . .
C6 C 0.6670(7) 0.4264(7) 0.0729(4) 0.0234(14) Uani 1 1 d . . . . .
H6 H 0.767679 0.468315 0.060062 0.028 Uiso 1 1 calc R . . . .
C2 C 0.4924(7) 0.1136(7) 0.2513(4) 0.0227(14) Uani 1 1 d . . . . .
H2 H 0.370039 0.109947 0.241305 0.027 Uiso 1 1 calc R . . . .
C9 C 0.3822(7) 0.3015(6) 0.1156(3) 0.0204(14) Uani 1 1 d . . . . .
C3 C 0.5899(8) 0.0391(7) 0.3065(4) 0.0262(15) Uani 1 1 d . . . . .
H3 H 0.538407 -0.017347 0.337052 0.031 Uiso 1 1 calc R . . . .
C9B C 0.3580(7) 0.8943(7) 0.0525(4) 0.0225(14) Uani 1 1 d . . . . .
H9B H 0.249626 0.916177 0.026525 0.027 Uiso 1 1 calc R . . . .
C5 C 0.5572(7) 0.2794(6) 0.1528(4) 0.0199(14) Uani 1 1 d . . . . .
C3B C 0.6150(8) 0.6299(6) 0.2582(4) 0.0219(14) Uani 1 1 d . . . . .
H3B H 0.735469 0.647995 0.260627 0.026 Uiso 1 1 calc R . . . .
C12 C 1.2202(8) 0.0464(7) 0.4494(4) 0.0275(16) Uani 1 1 d . . . . .
H12A H 1.270206 -0.011952 0.411212 0.033 Uiso 1 1 calc R . . . .
H12B H 1.181208 -0.017310 0.482784 0.033 Uiso 1 1 calc R . . . .
C13B C 0.2393(9) 0.5914(8) 0.4965(4) 0.0330(18) Uani 1 1 d . . . . .
H13D H 0.348313 0.555448 0.489984 0.049 Uiso 1 1 calc GR . . . .
H13E H 0.163049 0.515201 0.508272 0.049 Uiso 1 1 calc GR . . . .
H13F H 0.263054 0.672740 0.538521 0.049 Uiso 1 1 calc GR . . . .
C4B C 0.4873(7) 0.6841(7) 0.2076(4) 0.0230(14) Uani 1 1 d . . . . .
C2B C 0.5412(8) 0.5431(7) 0.3062(4) 0.0257(15) Uani 1 1 d . . . . .
H2B H 0.609085 0.498351 0.343301 0.031 Uiso 1 1 calc R . . . .
C4 C 0.7670(8) 0.0591(7) 0.3103(3) 0.0226(15) Uani 1 1 d . . . . .
C1B C 0.3613(8) 0.5320(7) 0.2924(4) 0.0240(14) Uani 1 1 d . . . . .
C13 C 1.3619(9) 0.1654(8) 0.4985(4) 0.0353(19) Uani 1 1 d . . . . .
H13A H 1.391466 0.234636 0.466673 0.053 Uiso 1 1 calc GR . . . .
H13B H 1.465278 0.122146 0.518882 0.053 Uiso 1 1 calc GR . . . .
H13C H 1.317953 0.214339 0.540934 0.053 Uiso 1 1 calc GR . . . .
C8 C 0.3555(7) 0.3879(6) 0.0546(3) 0.0205(14) Uani 1 1 d . . . . .
C11B C 0.0902(8) 0.5122(8) 0.3524(4) 0.0304(17) Uani 1 1 d . . . . .
H11C H 0.011401 0.440085 0.367142 0.037 Uiso 1 1 calc R . . . .
H11D H 0.023082 0.548995 0.308576 0.037 Uiso 1 1 calc R . . . .


_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 N3 1.610(5) . ?
S1 N2 1.625(6) . ?
S10B N12B 1.621(5) . ?
S10B N11B 1.609(5) . ?
S2 C1 1.730(6) . ?
S2 C4 1.733(7) . ?
S11B C4B 1.742(6) . ?
S11B C1B 1.730(6) . ?
N3 C9 1.352(8) . ?
N2 C8 1.356(7) . ?
N12B C6B 1.353(7) . ?
N11B C7B 1.357(7) . ?
N10B C5B 1.324(7) . ?
N10B C9B 1.364(8) . ?
N1 C6 1.358(9) . ?
N1 C5 1.326(8) . ?
C5B C6B 1.423(8) . ?
C5B C4B 1.450(9) . ?
C7B C6B 1.442(9) . ?
C7B C8B 1.433(7) . ?
C10B C1B 1.509(9) . ?
C10B C11B 1.536(9) . ?
C11 C10 1.527(8) . ?
C11 C12 1.522(8) . ?
C10 C4 1.504(8) . ?
C7 C7 1.483(12) 2_665 ?
C7 C6 1.392(8) . ?
C7 C8 1.437(8) . ?
C12B C13B 1.519(10) . ?
C12B C11B 1.547(9) . ?
C8B C8B 1.478(12) 2_675 ?
C8B C9B 1.388(8) . ?
C1 C2 1.384(9) . ?
C1 C5 1.444(9) . ?
C2 C3 1.416(9) . ?
C9 C5 1.434(8) . ?
C9 C8 1.434(9) . ?
C3 C4 1.363(9) . ?
C3B C4B 1.381(8) . ?
C3B C2B 1.423(9) . ?
C12 C13 1.526(9) . ?
C2B C1B 1.365(9) . ?

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
N3 S1 N2 101.4(3) . . ?
N11B S10B N12B 101.1(3) . . ?
C1 S2 C4 92.0(3) . . ?
C1B S11B C4B 91.8(3) . . ?
C9 N3 S1 106.2(4) . . ?
C8 N2 S1 105.9(4) . . ?
C6B N12B S10B 105.8(4) . . ?
C7B N11B S10B 107.4(4) . . ?
C5B N10B C9B 120.1(5) . . ?
C5 N1 C6 121.2(5) . . ?
N10B C5B C6B 119.5(6) . . ?
N10B C5B C4B 116.8(5) . . ?
C6B C5B C4B 123.7(5) . . ?
N11B C7B C6B 111.6(5) . . ?
N11B C7B C8B 128.4(6) . . ?
C8B C7B C6B 120.0(5) . . ?
C1B C10B C11B 114.0(5) . . ?
N12B C6B C5B 126.1(6) . . ?
N12B C6B C7B 114.1(5) . . ?
C5B C6B C7B 119.8(5) . . ?
C12 C11 C10 113.6(5) . . ?
C4 C10 C11 114.0(5) . . ?
C6 C7 C7 121.4(6) . 2_665 ?
C6 C7 C8 113.8(5) . . ?
C8 C7 C7 124.8(6) . 2_665 ?
C13B C12B C11B 112.9(5) . . ?
C7B C8B C8B 124.6(6) . 2_675 ?
C9B C8B C7B 113.6(5) . . ?
C9B C8B C8B 121.8(6) . 2_675 ?
C2 C1 S2 110.4(5) . . ?
C2 C1 C5 132.6(5) . . ?
C5 C1 S2 117.0(5) . . ?
N1 C6 C7 126.6(5) . . ?
C1 C2 C3 113.3(5) . . ?
N3 C9 C5 126.0(6) . . ?
N3 C9 C8 113.5(5) . . ?
C5 C9 C8 120.5(5) . . ?
C4 C3 C2 112.8(6) . . ?
N10B C9B C8B 127.1(5) . . ?
N1 C5 C1 117.2(5) . . ?
N1 C5 C9 118.1(6) . . ?
C9 C5 C1 124.7(5) . . ?
C4B C3B C2B 112.3(5) . . ?
C11 C12 C13 111.5(5) . . ?
C5B C4B S11B 118.2(4) . . ?
C3B C4B S11B 111.0(5) . . ?
C3B C4B C5B 130.8(5) . . ?
C1B C2B C3B 113.5(6) . . ?
C10 C4 S2 118.5(5) . . ?
C3 C4 S2 111.5(5) . . ?
C3 C4 C10 130.0(6) . . ?
C10B C1B S11B 120.6(4) . . ?
C2B C1B S11B 111.4(5) . . ?
C2B C1B C10B 127.5(6) . . ?
N2 C8 C7 127.3(6) . . ?
N2 C8 C9 113.0(5) . . ?
C9 C8 C7 119.7(5) . . ?
C10B C11B C12B 115.3(5) . . ?

_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 1.896
_oxdiff_exptl_absorpt_empirical_full_min 0.209
