# Supplementary Information (SI) for RSC Advances.
# 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_rdsdx2_010223
_database_code_depnum_ccdc_archive 'CCDC 2294084'
_audit_update_record             
;
2023-09-10 deposited with the CCDC.	2025-01-22 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1.333(C14 H9 N5)'
_chemical_formula_sum            'C24 H14 N4'
_chemical_formula_weight         358.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H14N4
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4775(3)
_cell_length_b                   7.5290(3)
_cell_length_c                   15.5021(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.249(3)
_cell_angle_gamma                90
_cell_volume                     1219.52(7)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    5562
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4750
_cell_measurement_theta_min      1.9520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             558
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12049
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.115
_diffrn_reflns_theta_min         1.949
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  11.00   0.50   60.92    --   10.00  25.00 126.00   50
  2  ω    -14.00  11.00   0.50   60.92    --   10.00 -25.00 -37.00   50
  3  ω    -35.00 -10.00   0.50   60.92    --  -10.20 -25.00 -37.00   50
  4  ω    -29.00  -2.00   0.50   60.92    --  -10.20  25.00 126.00   54
  5  ω    -15.00  30.00   0.50   60.92    --   10.00  77.00 150.00   90
  6  ω    -14.00  70.00   0.50   60.92    --   10.00  77.00-150.00  168
  7  ω    -66.00  32.00   0.50   60.92    --   10.00 -82.00-120.00  196
  8  ω    -79.00  43.00   0.50   60.92    --   10.00 -38.00 -60.00  244
  9  ω     43.00  68.00   0.50   60.92    --   10.00  77.00 150.00   50
 10  ω    -42.00  15.00   0.50   60.92    --  -10.20 -77.00 120.00  114
 11  ω    -97.00 -54.00   0.50   60.92    --  -10.20 -77.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0335909000
_diffrn_orient_matrix_UB_12      -0.0226451000
_diffrn_orient_matrix_UB_13      0.0365350000
_diffrn_orient_matrix_UB_21      0.0586971000
_diffrn_orient_matrix_UB_22      -0.0218135000
_diffrn_orient_matrix_UB_23      0.0233485000
_diffrn_orient_matrix_UB_31      0.0058708000
_diffrn_orient_matrix_UB_32      0.0887783000
_diffrn_orient_matrix_UB_33      0.0150486000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1930
_reflns_number_total             2540
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+0.0386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00C), C00C(H00D), C00D(H00E), C00E(H00F), C00I(H00I),
 C00J(H00J)
2.b X=CH2 refined with riding coordinates:
 N003(H00A,H00B)
;
_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
N001 N 0.71761(9) 0.36006(13) 0.56052(7) 0.0359(3) Uani 1 1 d . . . . .
N002 N 1.14947(9) 0.22546(13) 0.45360(7) 0.0386(3) Uani 1 1 d . . . . .
N003 N 0.60185(10) 0.67397(14) 0.61171(8) 0.0489(3) Uani 1 1 d . . . . .
H00A H 0.674493 0.682617 0.589606 0.059 Uiso 1 1 calc R U . . .
H00B H 0.564476 0.767675 0.629125 0.059 Uiso 1 1 calc R U . . .
C004 C 0.92584(11) 0.14503(14) 0.41560(8) 0.0308(3) Uani 1 1 d . . . . .
C005 C 0.89101(11) 0.22850(14) 0.49324(8) 0.0310(3) Uani 1 1 d . . . . .
C006 C 1.05737(11) 0.14637(14) 0.39928(8) 0.0325(3) Uani 1 1 d . . . . .
C007 C 0.54716(11) 0.51522(16) 0.61900(8) 0.0356(3) Uani 1 1 d . . . . .
C008 C 0.59738(11) 0.35720(16) 0.59363(8) 0.0348(3) Uani 1 1 d . . . . .
C009 C 0.75913(11) 0.22733(16) 0.51969(8) 0.0350(3) Uani 1 1 d . . . . .
H009 H 0.706198 0.130320 0.506726 0.042 Uiso 1 1 calc R U . . .
C00A C 0.98552(12) 0.30489(15) 0.54619(8) 0.0361(3) Uani 1 1 d . . . . .
H00C H 0.965409 0.359389 0.597286 0.043 Uiso 1 1 calc R U . . .
N00B N 0.48501(12) 0.05706(16) 0.61146(10) 0.0630(4) Uani 1 1 d . . . . .
C00C C 1.11218(12) 0.30151(16) 0.52396(9) 0.0393(3) Uani 1 1 d . . . . .
H00D H 1.173944 0.356282 0.561087 0.047 Uiso 1 1 calc R U . . .
C00D C 1.09703(13) 0.06141(16) 0.32443(8) 0.0407(3) Uani 1 1 d . . . . .
H00E H 1.183249 0.060175 0.313868 0.049 Uiso 1 1 calc R U . . .
C00E C 0.83792(12) 0.06393(17) 0.35404(8) 0.0414(3) Uani 1 1 d . . . . .
H00F H 0.750964 0.064927 0.362478 0.050 Uiso 1 1 calc R U . . .
C00F C 0.53022(12) 0.19388(18) 0.60375(9) 0.0419(3) Uani 1 1 d . . . . .
C00G C 0.42432(12) 0.51410(18) 0.65543(9) 0.0429(4) Uani 1 1 d . . . . .
N00H N 0.32739(13) 0.51600(19) 0.68405(10) 0.0695(4) Uani 1 1 d . . . . .
C00I C 1.01008(15) -0.01822(18) 0.26799(9) 0.0475(4) Uani 1 1 d . . . . .
H00I H 1.037197 -0.075000 0.219300 0.057 Uiso 1 1 calc R U . . .
C00J C 0.88001(15) -0.01569(18) 0.28239(9) 0.0493(4) Uani 1 1 d . . . . .
H00J H 0.821300 -0.069049 0.242550 0.059 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
N001 C008 1.3951(14) . ?
N001 C009 1.2765(15) . ?
N002 C006 1.3691(16) . ?
N002 C00C 1.3167(16) . ?
N003 H00A 0.8600 . ?
N003 H00B 0.8600 . ?
N003 C007 1.3339(15) . ?
C004 C005 1.4289(16) . ?
C004 C006 1.4194(16) . ?
C004 C00E 1.4149(17) . ?
C005 C009 1.4701(16) . ?
C005 C00A 1.3656(17) . ?
C006 C00D 1.4142(17) . ?
C007 C008 1.3703(17) . ?
C007 C00G 1.4433(17) . ?
C008 C00F 1.4311(17) . ?
C009 H009 0.9300 . ?
C00A H00C 0.9300 . ?
C00A C00C 1.3958(17) . ?
N00B C00F 1.1438(16) . ?
C00C H00D 0.9300 . ?
C00D H00E 0.9300 . ?
C00D C00I 1.355(2) . ?
C00E H00F 0.9300 . ?
C00E C00J 1.3638(18) . ?
C00G N00H 1.1381(16) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.3974(19) . ?
C00J H00J 0.9300 . ?

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
C009 N001 C008 121.37(10) . . ?
C00C N002 C006 117.37(10) . . ?
H00A N003 H00B 120.0 . . ?
C007 N003 H00A 120.0 . . ?
C007 N003 H00B 120.0 . . ?
C006 C004 C005 117.32(11) . . ?
C00E C004 C005 124.31(11) . . ?
C00E C004 C006 118.36(11) . . ?
C004 C005 C009 122.43(10) . . ?
C00A C005 C004 118.19(10) . . ?
C00A C005 C009 119.31(11) . . ?
N002 C006 C004 122.88(10) . . ?
N002 C006 C00D 117.70(11) . . ?
C00D C006 C004 119.42(11) . . ?
N003 C007 C008 125.25(11) . . ?
N003 C007 C00G 116.07(11) . . ?
C008 C007 C00G 118.67(11) . . ?
N001 C008 C00F 121.22(10) . . ?
C007 C008 N001 117.94(10) . . ?
C007 C008 C00F 120.80(10) . . ?
N001 C009 C005 119.70(11) . . ?
N001 C009 H009 120.1 . . ?
C005 C009 H009 120.1 . . ?
C005 C00A H00C 119.9 . . ?
C005 C00A C00C 120.28(11) . . ?
C00C C00A H00C 119.9 . . ?
N002 C00C C00A 123.94(12) . . ?
N002 C00C H00D 118.0 . . ?
C00A C00C H00D 118.0 . . ?
C006 C00D H00E 119.8 . . ?
C00I C00D C006 120.36(12) . . ?
C00I C00D H00E 119.8 . . ?
C004 C00E H00F 119.8 . . ?
C00J C00E C004 120.35(12) . . ?
C00J C00E H00F 119.8 . . ?
N00B C00F C008 174.93(13) . . ?
N00H C00G C007 178.94(15) . . ?
C00D C00I H00I 119.7 . . ?
C00D C00I C00J 120.51(12) . . ?
C00J C00I H00I 119.7 . . ?
C00E C00J C00I 120.94(13) . . ?
C00E C00J H00J 119.5 . . ?
C00I C00J H00J 119.5 . . ?

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
N002 C006 C00D C00I -179.60(11) . . . . ?
N003 C007 C008 N001 2.6(2) . . . . ?
N003 C007 C008 C00F -179.51(13) . . . . ?
C004 C005 C009 N001 -146.87(12) . . . . ?
C004 C005 C00A C00C 0.41(17) . . . . ?
C004 C006 C00D C00I 1.04(18) . . . . ?
C004 C00E C00J C00I -0.3(2) . . . . ?
C005 C004 C006 N002 -0.97(16) . . . . ?
C005 C004 C006 C00D 178.36(11) . . . . ?
C005 C004 C00E C00J -178.76(12) . . . . ?
C005 C00A C00C N002 -0.91(19) . . . . ?
C006 N002 C00C C00A 0.41(18) . . . . ?
C006 C004 C005 C009 -176.57(10) . . . . ?
C006 C004 C005 C00A 0.46(16) . . . . ?
C006 C004 C00E C00J 2.09(18) . . . . ?
C006 C00D C00I C00J 0.77(19) . . . . ?
C008 N001 C009 C005 -174.03(11) . . . . ?
C009 N001 C008 C007 -165.53(12) . . . . ?
C009 N001 C008 C00F 16.64(19) . . . . ?
C009 C005 C00A C00C 177.54(11) . . . . ?
C00A C005 C009 N001 36.13(17) . . . . ?
C00C N002 C006 C004 0.54(17) . . . . ?
C00C N002 C006 C00D -178.80(11) . . . . ?
C00D C00I C00J C00E -1.2(2) . . . . ?
C00E C004 C005 C009 4.27(18) . . . . ?
C00E C004 C005 C00A -178.69(11) . . . . ?
C00E C004 C006 N002 178.23(11) . . . . ?
C00E C004 C006 C00D -2.44(16) . . . . ?
C00G C007 C008 N001 -178.46(11) . . . . ?
C00G C007 C008 C00F -0.61(19) . . . . ?

_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 3.262
_oxdiff_exptl_absorpt_empirical_full_min 0.514
