# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_tmp-tcnb-0414-1
_database_code_depnum_ccdc_archive 'CCDC 2271812'
loop_
_audit_author_name
_audit_author_address
TMBZ-TCNB
;Tianjin University
China
;
_audit_update_record             
;
2023-06-23 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2022-04-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        TMBZ-TCNB
_chemical_formula_moiety         'C8 H10 N, C5 H N2'
_chemical_formula_sum            'C13 H11 N3'
_chemical_formula_weight         209.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHN
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'

_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                   7.6949(7)
_cell_length_b                   8.0542(7)
_cell_length_c                   9.7834(8)
_cell_angle_alpha                101.397(7)
_cell_angle_beta                 104.755(7)
_cell_angle_gamma                101.687(7)
_cell_volume                     553.95(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1992
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7920
_cell_measurement_theta_min      4.8180
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.792
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89921
_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            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             220
_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  0.0149
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3314
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.042
_diffrn_reflns_theta_max         67.042
_diffrn_reflns_theta_min         4.845
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  -2.00   1.00    1.78    --  -41.12 125.00   0.00   58
  2  ω   -117.00 -17.00   1.00    1.78    --  -41.12 -77.00 150.00  100
  3  ω    -68.00  27.00   1.00    1.78    --  -41.12  57.00 -90.00   95
  4  ω     33.00  72.00   1.00    1.78    --   41.12 -99.00   0.00   39
  5  ω      3.00  30.00   1.00    1.78    --   41.12 -99.00   0.00   27
  6  ω     77.00 104.00   1.00    7.14    --  105.32  30.00 -90.00   27
  7  ω     56.00 109.00   1.00    7.14    --  105.32 -94.00-150.00   53
  8  ω     58.00 122.00   1.00    7.14    --  105.32 -45.00-180.00   64
  9  ω    102.00 147.00   1.00    7.14    --  105.32 125.00  90.00   45
 10  ω     98.00 144.00   1.00    7.14    --  105.32 121.00 -26.00   46
 11  ω     35.00 132.00   1.00    7.14    --  105.32 -61.00  60.00   97
 12  ω     34.00 126.00   1.00    7.14    --  105.32 -30.00 -60.00   92
 13  ω    106.00 176.00   1.00    7.14    --  105.32  30.00 -90.00   70
 14  ω     51.00 125.00   1.00    7.14    --  105.32 -77.00 -60.00   74
 15  ω     74.00 117.00   1.00    7.14    --  105.32-125.00 150.00   43
 16  ω     78.00 151.00   1.00    7.14    --  105.32  30.00-180.00   73
;
_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      -0.2107030000
_diffrn_orient_matrix_UB_12      -0.0901348000
_diffrn_orient_matrix_UB_13      -0.0633071000
_diffrn_orient_matrix_UB_21      -0.0089784000
_diffrn_orient_matrix_UB_22      -0.0021056000
_diffrn_orient_matrix_UB_23      0.1551881000
_diffrn_orient_matrix_UB_31      -0.0408677000
_diffrn_orient_matrix_UB_32      0.1812747000
_diffrn_orient_matrix_UB_33      0.0199296000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1682
_reflns_number_total             1976
_reflns_odcompleteness_completeness 99.65
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0068(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.042
_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)+(0.0751P)²+0.0547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1308
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_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
N1 N 0.1472(2) 0.10220(19) 0.22595(17) 0.0716(4) Uani 1 1 d . . . . .
C1 C 0.1639(3) -0.0754(2) 0.2113(2) 0.0831(6) Uani 1 1 d . . . . .
H1A H 0.1184 -0.1387 0.1097 0.100 Uiso 1 1 calc R U . . .
H1B H 0.0919 -0.1327 0.2641 0.100 Uiso 1 1 calc R U . . .
H1C H 0.2924 -0.0730 0.2505 0.100 Uiso 1 1 calc R U . . .
C2 C -0.0253(3) 0.1283(3) 0.2480(2) 0.0871(6) Uani 1 1 d . . . . .
H2A H -0.1200 0.0975 0.1548 0.105 Uiso 1 1 calc R U . . .
H2B H -0.0066 0.2494 0.2963 0.105 Uiso 1 1 calc R U . . .
H2C H -0.0638 0.0555 0.3073 0.105 Uiso 1 1 calc R U . . .
C3 C 0.2420(2) 0.21135(19) 0.16015(15) 0.0554(4) Uani 1 1 d . . . . .
C4 C 0.1983(2) 0.3655(2) 0.13985(18) 0.0608(4) Uani 1 1 d . . . . .
H4 H 0.0999 0.3954 0.1685 0.073 Uiso 1 1 calc R U . . .
C5 C 0.2976(2) 0.4756(2) 0.07803(18) 0.0593(4) Uani 1 1 d . . . . .
H5 H 0.2630 0.5772 0.0659 0.071 Uiso 1 1 calc R U . . .
C6 C 0.44697(19) 0.44070(17) 0.03332(14) 0.0494(3) Uani 1 1 d . . . . .
C7 C 0.4911(2) 0.2871(2) 0.05591(19) 0.0627(4) Uani 1 1 d . . . . .
H7 H 0.5910 0.2585 0.0288 0.075 Uiso 1 1 calc R U . . .
C8 C 0.3926(2) 0.1750(2) 0.11697(19) 0.0653(4) Uani 1 1 d . . . . .
H8 H 0.4274 0.0736 0.1295 0.078 Uiso 1 1 calc R U . . .
N2 N 0.3506(2) 0.0527(2) 0.6040(2) 0.0819(5) Uani 1 1 d . . . . .
N3 N 0.9268(2) 0.5857(2) 0.3429(2) 0.0791(5) Uani 1 1 d . . . . .
C9 C 0.3922(2) 0.18133(19) 0.57366(18) 0.0591(4) Uani 1 1 d . . . . .
C10 C 0.44744(18) 0.34346(16) 0.53605(14) 0.0469(3) Uani 1 1 d . . . . .
C11 C 0.59563(19) 0.37150(18) 0.47910(16) 0.0525(4) Uani 1 1 d . . . . .
H11 H 0.6588 0.2858 0.4649 0.063 Uiso 1 1 calc R U . . .
C12 C 0.64827(17) 0.52842(16) 0.44361(14) 0.0459(3) Uani 1 1 d . . . . .
C13 C 0.8024(2) 0.55927(19) 0.38565(17) 0.0563(4) 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
N1 C1 1.445(3) . ?
N1 C2 1.447(2) . ?
N1 C3 1.3863(19) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.388(2) . ?
C3 C8 1.395(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C6 C6 1.485(3) 2_665 ?
C6 C7 1.391(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(2) . ?
C8 H8 0.9300 . ?
N2 C9 1.1401(19) . ?
N3 C13 1.1369(19) . ?
C9 C10 1.4374(18) . ?
C10 C11 1.3896(18) . ?
C10 C12 1.3958(19) 2_666 ?
C11 H11 0.9300 . ?
C11 C12 1.3855(18) . ?
C12 C10 1.3958(19) 2_666 ?
C12 C13 1.4384(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
C1 N1 C2 114.92(15) . . ?
C3 N1 C1 119.74(15) . . ?
C3 N1 C2 119.38(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 122.19(15) . . ?
N1 C3 C8 121.17(15) . . ?
C4 C3 C8 116.58(14) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.52(15) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.66(14) . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C6 122.45(16) . 2_665 ?
C5 C6 C7 115.36(14) . . ?
C7 C6 C6 122.19(16) . 2_665 ?
C6 C7 H7 118.6 . . ?
C8 C7 C6 122.72(15) . . ?
C8 C7 H7 118.6 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.16(15) . . ?
C7 C8 H8 119.4 . . ?
N2 C9 C10 179.15(17) . . ?
C11 C10 C9 119.75(12) . . ?
C11 C10 C12 120.34(12) . 2_666 ?
C12 C10 C9 119.90(12) 2_666 . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.34(12) . . ?
C12 C11 H11 120.3 . . ?
C10 C12 C13 119.92(11) 2_666 . ?
C11 C12 C10 120.32(12) . 2_666 ?
C11 C12 C13 119.76(12) . . ?
N3 C13 C12 178.48(19) . . ?

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
N1 C3 C4 C5 178.05(14) . . . . ?
N1 C3 C8 C7 -177.76(15) . . . . ?
C1 N1 C3 C4 164.21(16) . . . . ?
C1 N1 C3 C8 -18.8(2) . . . . ?
C2 N1 C3 C4 12.7(2) . . . . ?
C2 N1 C3 C8 -170.27(16) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C3 C8 C7 -0.6(2) . . . . ?
C4 C5 C6 C6 179.89(16) . . . 2_665 ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C6 C7 C8 -179.56(16) 2_665 . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C8 C3 C4 C5 0.9(2) . . . . ?
C9 C10 C11 C12 -179.79(13) . . . . ?
C10 C11 C12 C10 -0.4(2) . . . 2_666 ?
C10 C11 C12 C13 179.52(13) . . . . ?
C12 C10 C11 C12 0.4(2) 2_666 . . . ?

_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.747
