# Supplementary Information (SI) for Nanoscale.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_d8v23273
_database_code_depnum_ccdc_archive 'CCDC 2502102'
loop_
_audit_author_name
_audit_author_address
'Fei Tong'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2025-11-11 deposited with the CCDC.	2025-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.0461(5)
_cell_length_b                   12.8296(4)
_cell_length_c                   17.1929(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3098.26(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    4689
_cell_measurement_theta_min      4.738
_cell_measurement_theta_max      54.777

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20335
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3043
_reflns_number_gt                2112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+1.2390P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.46175(15) 0.71893(13) 0.31398(11) 0.0543(6) Uani 1 1 d . . . . .
N2 N 0.60116(14) 0.32054(12) 0.44064(12) 0.0506(5) Uani 1 1 d . . . . .
C1 C 0.64684(13) 0.83479(13) 0.43512(11) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.62733(13) 0.89550(13) 0.50146(11) 0.0310(4) Uani 1 1 d . . . . .
C3 C 0.60895(14) 0.85192(15) 0.57604(12) 0.0382(5) Uani 1 1 d . . . . .
H3 H 0.6095 0.7791 0.5821 0.046 Uiso 1 1 calc R U . . .
C4 C 0.59068(16) 0.91312(16) 0.63854(13) 0.0450(5) Uani 1 1 d . . . . .
H4 H 0.5799 0.8823 0.6873 0.054 Uiso 1 1 calc R U . . .
C5 C 0.58770(15) 1.02317(16) 0.63117(13) 0.0455(6) Uani 1 1 d . . . . .
H5 H 0.5747 1.0648 0.6749 0.055 Uiso 1 1 calc R U . . .
C6 C 0.60356(14) 1.06806(15) 0.56141(12) 0.0396(5) Uani 1 1 d . . . . .
H6 H 0.6014 1.1411 0.5571 0.048 Uiso 1 1 calc R U . . .
C7 C 0.62355(13) 1.00712(14) 0.49420(12) 0.0327(5) Uani 1 1 d . . . . .
C8 C 0.63838(13) 1.05223(13) 0.42178(12) 0.0356(5) Uani 1 1 d . . . . .
H8 H 0.6343 1.1251 0.4170 0.043 Uiso 1 1 calc R U . . .
C9 C 0.65901(13) 0.99322(14) 0.35626(12) 0.0340(5) Uani 1 1 d . . . . .
C10 C 0.67358(15) 1.04010(16) 0.28217(13) 0.0433(5) Uani 1 1 d . . . . .
H10 H 0.6671 1.1127 0.2770 0.052 Uiso 1 1 calc R U . . .
C11 C 0.69641(16) 0.98284(18) 0.21930(13) 0.0507(6) Uani 1 1 d . . . . .
H11 H 0.7049 1.0154 0.1708 0.061 Uiso 1 1 calc R U . . .
C12 C 0.70757(16) 0.87379(17) 0.22608(13) 0.0508(6) Uani 1 1 d . . . . .
H12 H 0.7258 0.8345 0.1824 0.061 Uiso 1 1 calc R U . . .
C13 C 0.69225(15) 0.82530(15) 0.29483(12) 0.0418(5) Uani 1 1 d . . . . .
H13 H 0.6998 0.7526 0.2979 0.050 Uiso 1 1 calc R U . . .
C14 C 0.66498(13) 0.88162(14) 0.36278(12) 0.0325(5) Uani 1 1 d . . . . .
C15 C 0.64892(14) 0.72015(13) 0.44446(11) 0.0333(5) Uani 1 1 d . . . . .
H15 H 0.6947 0.6927 0.4787 0.040 Uiso 1 1 calc R U . . .
C16 C 0.59165(14) 0.65196(13) 0.40859(11) 0.0316(4) Uani 1 1 d . . . . .
C17 C 0.51970(15) 0.69039(13) 0.35577(12) 0.0365(5) Uani 1 1 d . . . . .
C18 C 0.59455(13) 0.53745(13) 0.41977(11) 0.0320(4) Uani 1 1 d . . . . .
C19 C 0.56008(15) 0.46992(14) 0.36340(12) 0.0411(5) Uani 1 1 d . . . . .
H19 H 0.5332 0.4959 0.3172 0.049 Uiso 1 1 calc R U . . .
C20 C 0.56588(17) 0.36356(16) 0.37625(14) 0.0514(6) Uani 1 1 d . . . . .
H20 H 0.5435 0.3188 0.3370 0.062 Uiso 1 1 calc R U . . .
C21 C 0.63239(15) 0.38637(15) 0.49442(13) 0.0431(5) Uani 1 1 d . . . . .
H21 H 0.6572 0.3581 0.5406 0.052 Uiso 1 1 calc R U . . .
C22 C 0.63094(14) 0.49357(14) 0.48709(12) 0.0362(5) Uani 1 1 d . . . . .
H22 H 0.6543 0.5362 0.5273 0.043 Uiso 1 1 calc R U . . .


_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 C17 1.146(3) . ?
N2 C21 1.327(3) . ?
N2 C20 1.333(3) . ?
C1 C14 1.404(3) . ?
C1 C2 1.408(2) . ?
C1 C15 1.480(2) . ?
C2 C3 1.422(3) . ?
C2 C7 1.438(2) . ?
C3 C4 1.355(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.418(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.349(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.423(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.389(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.423(3) . ?
C9 C14 1.439(2) . ?
C10 C11 1.346(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.413(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.353(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.426(3) . ?
C13 H13 0.9400 . ?
C15 C16 1.339(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.445(3) . ?
C16 C18 1.482(2) . ?
C18 C22 1.385(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?

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
C21 N2 C20 116.00(17) . . ?
C14 C1 C2 121.07(16) . . ?
C14 C1 C15 121.17(16) . . ?
C2 C1 C15 117.76(17) . . ?
C1 C2 C3 123.23(16) . . ?
C1 C2 C7 119.18(18) . . ?
C3 C2 C7 117.58(17) . . ?
C4 C3 C2 121.42(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.97(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.33(18) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.91(17) . . ?
C8 C7 C2 119.15(17) . . ?
C6 C7 C2 118.93(18) . . ?
C9 C8 C7 122.13(16) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 121.73(17) . . ?
C8 C9 C14 119.45(18) . . ?
C10 C9 C14 118.81(19) . . ?
C11 C10 C9 121.49(19) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.69(19) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C1 C14 C13 123.88(16) . . ?
C1 C14 C9 118.96(17) . . ?
C13 C14 C9 117.13(18) . . ?
C16 C15 C1 125.99(18) . . ?
C16 C15 H15 117.0 . . ?
C1 C15 H15 117.0 . . ?
C15 C16 C17 119.11(17) . . ?
C15 C16 C18 124.84(18) . . ?
C17 C16 C18 116.03(16) . . ?
N1 C17 C16 178.6(2) . . ?
C22 C18 C19 117.32(17) . . ?
C22 C18 C16 121.43(17) . . ?
C19 C18 C16 121.25(18) . . ?
C20 C19 C18 118.9(2) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
N2 C20 C19 124.2(2) . . ?
N2 C20 H20 117.9 . . ?
C19 C20 H20 117.9 . . ?
N2 C21 C22 124.4(2) . . ?
N2 C21 H21 117.8 . . ?
C22 C21 H21 117.8 . . ?
C21 C22 C18 119.10(19) . . ?
C21 C22 H22 120.4 . . ?
C18 C22 H22 120.4 . . ?

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
C14 C1 C2 C3 -179.70(18) . . . . ?
C15 C1 C2 C3 -0.5(3) . . . . ?
C14 C1 C2 C7 1.6(3) . . . . ?
C15 C1 C2 C7 -179.20(17) . . . . ?
C1 C2 C3 C4 179.84(19) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 178.9(2) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C1 C2 C7 C8 0.6(3) . . . . ?
C3 C2 C7 C8 -178.14(17) . . . . ?
C1 C2 C7 C6 179.84(17) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
C6 C7 C8 C9 179.22(18) . . . . ?
C2 C7 C8 C9 -1.5(3) . . . . ?
C7 C8 C9 C10 179.64(19) . . . . ?
C7 C8 C9 C14 0.3(3) . . . . ?
C8 C9 C10 C11 178.0(2) . . . . ?
C14 C9 C10 C11 -2.7(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 2.3(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C2 C1 C14 C13 175.05(18) . . . . ?
C15 C1 C14 C13 -4.1(3) . . . . ?
C2 C1 C14 C9 -2.9(3) . . . . ?
C15 C1 C14 C9 177.99(17) . . . . ?
C12 C13 C14 C1 179.0(2) . . . . ?
C12 C13 C14 C9 -3.0(3) . . . . ?
C8 C9 C14 C1 1.9(3) . . . . ?
C10 C9 C14 C1 -177.45(17) . . . . ?
C8 C9 C14 C13 -176.15(17) . . . . ?
C10 C9 C14 C13 4.5(3) . . . . ?
C14 C1 C15 C16 -62.1(3) . . . . ?
C2 C1 C15 C16 118.7(2) . . . . ?
C1 C15 C16 C17 -0.4(3) . . . . ?
C1 C15 C16 C18 -179.22(18) . . . . ?
C15 C16 C18 C22 24.1(3) . . . . ?
C17 C16 C18 C22 -154.68(18) . . . . ?
C15 C16 C18 C19 -156.4(2) . . . . ?
C17 C16 C18 C19 24.8(3) . . . . ?
C22 C18 C19 C20 -1.6(3) . . . . ?
C16 C18 C19 C20 178.98(19) . . . . ?
C21 N2 C20 C19 -0.3(3) . . . . ?
C18 C19 C20 N2 1.4(3) . . . . ?
C20 N2 C21 C22 -0.5(3) . . . . ?
N2 C21 C22 C18 0.2(3) . . . . ?
C19 C18 C22 C21 0.8(3) . . . . ?
C16 C18 C22 C21 -179.70(18) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

