# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2530205'
loop_
_audit_author_name
_audit_author_address
'Alex Andrews P'
;IISER Thiruvananthapuram 
India
;
_audit_update_record             
;
2026-05-04 deposited with the CCDC.	2026-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10H8, C10H2N4'
_chemical_formula_sum            'C20 H10 N4'
_chemical_formula_weight         306.32

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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.3261(3)
_cell_length_b                   12.5443(4)
_cell_length_c                   6.6892(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.9040(10)
_cell_angle_gamma                90
_cell_volume                     744.67(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4906
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      28.29

_exptl_crystal_description       'rectangular block'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   
;   
Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed microfocus tube'
_diffrn_measurement_device_type  'Bruker Apex3 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11017
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.812
_diffrn_reflns_theta_max         28.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             969
_reflns_number_gt                909
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0502P)²+0.3546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/3 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         969
_refine_ls_number_parameters     71
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_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
C1 C 0.27602(9) 0.11352(6) 0.12016(12) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.13536(8) 0.05613(6) 0.05836(11) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.000000 0.11214(9) 0.000000 0.0142(2) Uani 1 2 d S T P . .
H3 H -0.000002 0.186280 -0.000002 0.017 Uiso 1 2 calc R U P . .
N1 N 0.38813(8) 0.15900(6) 0.17011(11) 0.0215(2) Uani 1 1 d . . . . .
C5 C 0.21414(10) 0.09596(7) 0.59522(13) 0.0216(2) Uani 1 1 d D . . . .
C6 C 0.29242(13) 0.000000 0.62994(18) 0.0218(3) Uani 1 2 d S T P . .
H6 H 0.397212 0.000000 0.676418 0.026 Uiso 1 2 calc R U P . .
C7 C -0.06745(19) 0.12724(15) 0.4740(2) 0.0176(3) Uani 0.5 1 d . . P . .
H7 H -0.048441 0.200122 0.486093 0.021 Uiso 0.5 1 calc R U P . .
C8 C 0.05600(18) 0.05965(14) 0.5282(2) 0.0149(3) Uani 0.5 1 d . . P . .
H5 H 0.2669(14) 0.1600(6) 0.622(2) 0.048(4) Uiso 1 1 d 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
C1 N1 1.1470(11) . ?
C1 C2 1.4411(10) . ?
C2 C3 1.3917(9) . ?
C2 C2 1.4081(15) 6 ?
C3 H3 0.9300 . ?
C5 C7 1.3603(19) 2_556 ?
C5 C6 1.3899(11) . ?
C5 C8 1.4755(17) . ?
C5 H5 0.9302(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(2) . ?
C7 H7 0.9300 . ?
C8 C8 1.496(4) 6 ?

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
N1 C1 C2 179.72(9) . . ?
C3 C2 C2 120.33(5) . 6 ?
C3 C2 C1 119.70(7) . . ?
C2 C2 C1 119.98(4) 6 . ?
C2 C3 C2 119.35(10) . 2 ?
C2 C3 H3 120.3 . . ?
C2 C3 H3 120.3 2 . ?
C7 C5 C6 136.75(12) 2_556 . ?
C7 C5 C8 34.81(9) 2_556 . ?
C6 C5 C8 102.00(10) . . ?
C7 C5 H5 103.5(9) 2_556 . ?
C6 C5 H5 119.8(9) . . ?
C8 C5 H5 138.2(9) . . ?
C5 C6 C5 120.02(11) 6 . ?
C5 C6 H6 120.0 6 . ?
C5 C6 H6 120.0 . . ?
C5 C7 C8 125.48(15) 2_556 . ?
C5 C7 H7 117.3 2_556 . ?
C8 C7 H7 117.3 . . ?
C5 C7 H7 154.74(15) 2_556 2_556 ?
C8 C7 H7 79.40(15) . 2_556 ?
H7 C7 H7 38.1 . 2_556 ?
C7 C8 C7 59.1(2) 2_556 . ?
C7 C8 C5 65.21(17) 2_556 . ?
C7 C8 C5 124.27(13) . . ?
C7 C8 C8 172.46(17) 2_556 6 ?
C7 C8 C8 127.74(9) . 6 ?
C5 C8 C8 107.98(8) . 6 ?

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
C2 C2 C3 C2 0.0 6 . . 2 ?
C1 C2 C3 C2 -179.65(7) . . . 2 ?
C7 C5 C6 C5 -1.7(2) 2_556 . . 6 ?
C8 C5 C6 C5 0.82(14) . . . 6 ?
C5 C7 C8 C7 174.5(3) 2_556 . . 2_556 ?
C5 C7 C8 C5 177.57(11) 2_556 . . . ?
C5 C7 C8 C8 -1.72(18) 2_556 . . 6 ?
C6 C5 C8 C7 -176.94(16) . . . 2_556 ?
C7 C5 C8 C7 -2.90(19) 2_556 . . . ?
C6 C5 C8 C7 -179.84(12) . . . . ?
C7 C5 C8 C8 176.51(16) 2_556 . . 6 ?
C6 C5 C8 C8 -0.43(8) . . . 6 ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.043



