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

 
data_d8v23273 
  
_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 
  
  
  
