# Supplementary Information (SI) for Molecular Systems Design & Engineering.
# 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_DHN_TCNQ
_database_code_depnum_ccdc_archive 'CCDC 2402657'
loop_
_audit_author_name
_audit_author_address
'Arkalekha Mandal'
;University of Oslo
Norway
;
_audit_update_record             
;
2024-11-14 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;

_vrf_THETM01_mo_akm_hydroxynap_TCNQ_n_0ma_a 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Diffraction was limited at higher angles due to low crystal quality.
;
_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H4 N4, C10 H8 O2'
_chemical_formula_sum            'C22 H12 N4 O2'
_chemical_formula_weight         364.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.126(2)
_cell_length_b                   18.086(5)
_cell_length_c                   7.382(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.671(7)
_cell_angle_gamma                90
_cell_volume                     871.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2684
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      20.73

_exptl_crystal_description       'flat needle'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Photon 100 CMOS detector, Bruker D8 Advance single crystal CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            10190
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         21.036
_diffrn_reflns_theta_full        21.036
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             936
_reflns_number_gt                719
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0739P)²+0.3132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         936
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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
O1 O 0.5170(4) 0.09373(12) -0.3260(3) 0.0553(8) Uani 1 1 d . . . . .
H1 H 0.533594 0.137830 -0.340684 0.083 Uiso 1 1 calc R U . . .
C11 C 0.4926(4) 0.00802(17) -0.0971(4) 0.0311(9) Uani 1 1 d . . . . .
C4 C 0.5312(5) 0.42878(17) 0.4411(4) 0.0310(9) Uani 1 1 d . . . . .
N2 N 0.5580(5) 0.33222(16) 0.0391(5) 0.0596(10) Uani 1 1 d . . . . .
C5 C 0.5416(5) 0.4417(2) 0.6357(5) 0.0346(9) Uani 1 1 d . . . . .
C2 C 0.5600(5) 0.35920(17) 0.3823(4) 0.0322(9) Uani 1 1 d . . . . .
C7 C 0.5294(5) 0.08179(18) -0.1390(5) 0.0363(9) Uani 1 1 d . . . . .
C6 C 0.5124(5) 0.50962(19) 0.6925(5) 0.0353(9) Uani 1 1 d . . . . .
N1 N 0.6160(6) 0.24571(18) 0.6059(5) 0.0636(11) Uani 1 1 d . . . . .
C3 C 0.5579(5) 0.34418(17) 0.1907(5) 0.0400(10) Uani 1 1 d . . . . .
C10 C 0.5547(5) 0.04942(18) 0.2378(5) 0.0389(10) Uani 1 1 d . . . . .
H10 H 0.564153 0.039528 0.364822 0.047 Uiso 1 1 calc R U . . .
C8 C 0.5733(5) 0.13506(19) -0.0003(5) 0.0423(10) Uani 1 1 d . . . . .
H8 H 0.595061 0.183279 -0.031091 0.051 Uiso 1 1 calc R U . . .
C1 C 0.5913(6) 0.2965(2) 0.5080(5) 0.0428(10) Uani 1 1 d . . . . .
C9 C 0.5862(5) 0.11869(19) 0.1882(5) 0.0435(10) Uani 1 1 d . . . . .
H9 H 0.617184 0.156183 0.281914 0.052 Uiso 1 1 calc R U . . .
H6 H 0.524(4) 0.5187(16) 0.827(5) 0.041(9) Uiso 1 1 d . . . . .
H5 H 0.574(5) 0.4037(19) 0.724(5) 0.047(10) Uiso 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
O1 C7 1.364(4) . ?
C11 C10 1.411(4) 3_655 ?
C11 C7 1.418(4) . ?
C11 C11 1.424(6) 3_655 ?
C4 C2 1.373(4) . ?
C4 C5 1.427(4) . ?
C4 C6 1.437(4) 3_666 ?
N2 C3 1.140(4) . ?
C5 C6 1.341(4) . ?
C2 C1 1.425(5) . ?
C2 C3 1.435(5) . ?
C7 C8 1.348(4) . ?
N1 C1 1.138(4) . ?
C10 C9 1.349(4) . ?
C8 C9 1.388(5) . ?

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
C10 C11 C7 122.9(3) 3_655 . ?
C10 C11 C11 119.4(4) 3_655 3_655 ?
C7 C11 C11 117.8(3) . 3_655 ?
C2 C4 C5 120.9(3) . . ?
C2 C4 C6 120.8(3) . 3_666 ?
C5 C4 C6 118.3(3) . 3_666 ?
C6 C5 C4 120.9(3) . . ?
C4 C2 C1 121.9(3) . . ?
C4 C2 C3 122.8(3) . . ?
C1 C2 C3 115.4(3) . . ?
C8 C7 O1 123.8(3) . . ?
C8 C7 C11 120.9(3) . . ?
O1 C7 C11 115.3(3) . . ?
C5 C6 C4 120.9(3) . 3_666 ?
N2 C3 C2 179.4(4) . . ?
C9 C10 C11 120.0(3) . 3_655 ?
C7 C8 C9 120.7(3) . . ?
N1 C1 C2 178.9(3) . . ?
C10 C9 C8 121.2(3) . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.078



