# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_ne-1
_database_code_depnum_ccdc_archive 'CCDC 2418900'
loop_
_audit_author_name
_audit_author_address
'Asato mizuno'
;KIT
Germany
;
_audit_update_record             
;
2025-01-22 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 N2'
_chemical_formula_sum            'C14 H10 N2'
_chemical_formula_weight         206.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N '
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   11.9000(2)
_cell_length_b                   7.30150(10)
_cell_length_c                   24.8756(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2161.39(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10144
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.0400
_cell_measurement_theta_min      2.3900
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.205
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20940
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         2.369
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00  300.60    --    0.00 180.00 254.00  180
  2  ω    -90.00 -30.00   1.00  300.60    --    0.00 180.00  62.00   60
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0465817000
_diffrn_orient_matrix_UB_12      0.0533671000
_diffrn_orient_matrix_UB_13      0.0084421000
_diffrn_orient_matrix_UB_21      -0.0370551000
_diffrn_orient_matrix_UB_22      0.0703850000
_diffrn_orient_matrix_UB_23      0.0084853000
_diffrn_orient_matrix_UB_31      -0.0029952000
_diffrn_orient_matrix_UB_32      -0.0404392000
_diffrn_orient_matrix_UB_33      0.0258834000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2028
_reflns_number_total             2379
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.4169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1242
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C10(H10), C11(H11), C6(H6), C12(H12), C2(H2), C4(H4),
 C1(H1), C3(H3)
;
_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
N2 N 0.55693(8) 0.75682(14) 0.39781(4) 0.0314(2) Uani 1 1 d . . . . .
N1 N 0.29117(9) 0.57803(17) 0.36831(4) 0.0381(3) Uani 1 1 d . . . . .
C8 C 0.36773(10) 0.63950(16) 0.38960(4) 0.0293(3) Uani 1 1 d . . . . .
C5 C 0.44980(10) 0.71981(16) 0.47911(5) 0.0288(3) Uani 1 1 d . . . . .
C7 C 0.46433(9) 0.71059(16) 0.41998(5) 0.0282(3) Uani 1 1 d . . . . .
C9 C 0.57333(10) 0.75855(16) 0.34150(4) 0.0298(3) Uani 1 1 d . . . . .
C14 C 0.67312(10) 0.68128(17) 0.32206(5) 0.0331(3) Uani 1 1 d . . . . .
H14 H 0.724181 0.624373 0.346205 0.040 Uiso 1 1 calc R U . . .
C13 C 0.69737(11) 0.68789(18) 0.26747(5) 0.0365(3) Uani 1 1 d . . . . .
H13 H 0.764070 0.632511 0.254201 0.044 Uiso 1 1 calc R U . . .
C10 C 0.50010(11) 0.84604(17) 0.30604(5) 0.0343(3) Uani 1 1 d . . . . .
H10 H 0.432512 0.899574 0.318932 0.041 Uiso 1 1 calc R U . . .
C11 C 0.52679(12) 0.85429(17) 0.25163(5) 0.0379(3) Uani 1 1 d . . . . .
H11 H 0.477434 0.914947 0.227469 0.045 Uiso 1 1 calc R U . . .
C6 C 0.53777(11) 0.78332(19) 0.51106(5) 0.0367(3) Uani 1 1 d . . . . .
H6 H 0.606159 0.821040 0.494760 0.044 Uiso 1 1 calc R U . . .
C12 C 0.62453(12) 0.77505(16) 0.23231(5) 0.0378(3) Uani 1 1 d . . . . .
H12 H 0.641609 0.780424 0.195038 0.045 Uiso 1 1 calc R U . . .
C2 C 0.42672(11) 0.73937(19) 0.59031(5) 0.0384(3) Uani 1 1 d . . . . .
H2 H 0.418710 0.746988 0.628237 0.046 Uiso 1 1 calc R U . . .
C4 C 0.35042(10) 0.6651(2) 0.50359(5) 0.0383(3) Uani 1 1 d . . . . .
H4 H 0.290127 0.620199 0.482309 0.046 Uiso 1 1 calc R U . . .
C1 C 0.52618(11) 0.79179(19) 0.56628(5) 0.0380(3) Uani 1 1 d . . . . .
H1 H 0.586905 0.833852 0.587776 0.046 Uiso 1 1 calc R U . . .
C3 C 0.33880(12) 0.6758(2) 0.55920(5) 0.0455(4) Uani 1 1 d . . . . .
H3 H 0.270412 0.639436 0.575747 0.055 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
N2 C7 1.2777(15) . ?
N2 C9 1.4144(15) . ?
N1 C8 1.1454(15) . ?
C8 C7 1.4703(16) . ?
C5 C7 1.4827(16) . ?
C5 C6 1.3936(16) . ?
C5 C4 1.3889(17) . ?
C9 C14 1.4007(16) . ?
C9 C10 1.3949(17) . ?
C14 H14 0.9500 . ?
C14 C13 1.3891(17) . ?
C13 H13 0.9500 . ?
C13 C12 1.3862(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.3915(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3851(18) . ?
C6 H6 0.9500 . ?
C6 C1 1.3819(17) . ?
C12 H12 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.3801(18) . ?
C2 C3 1.3816(19) . ?
C4 H4 0.9500 . ?
C4 C3 1.3923(17) . ?
C1 H1 0.9500 . ?
C3 H3 0.9500 . ?

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
C7 N2 C9 123.28(10) . . ?
N1 C8 C7 176.23(13) . . ?
C6 C5 C7 119.56(10) . . ?
C4 C5 C7 121.41(10) . . ?
C4 C5 C6 119.03(11) . . ?
N2 C7 C8 123.08(10) . . ?
N2 C7 C5 121.11(10) . . ?
C8 C7 C5 115.77(10) . . ?
C14 C9 N2 117.08(11) . . ?
C10 C9 N2 122.97(10) . . ?
C10 C9 C14 119.73(11) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.97(12) . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.19(11) . . ?
C12 C13 H13 119.9 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.49(11) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.74(12) . . ?
C12 C11 H11 119.6 . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.44(11) . . ?
C1 C6 H6 119.8 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.86(11) . . ?
C11 C12 H12 120.1 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.00(11) . . ?
C3 C2 H2 120.0 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.26(12) . . ?
C3 C4 H4 119.9 . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.24(12) . . ?
C2 C1 H1 119.9 . . ?
C2 C3 C4 120.01(12) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?

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
N2 C9 C14 C13 -176.33(11) . . . . ?
N2 C9 C10 C11 174.82(11) . . . . ?
C5 C6 C1 C2 -0.8(2) . . . . ?
C5 C4 C3 C2 -0.6(2) . . . . ?
C7 N2 C9 C14 -134.74(12) . . . . ?
C7 N2 C9 C10 50.76(17) . . . . ?
C7 C5 C6 C1 -179.56(12) . . . . ?
C7 C5 C4 C3 -179.75(13) . . . . ?
C9 N2 C7 C8 5.26(17) . . . . ?
C9 N2 C7 C5 -176.99(11) . . . . ?
C9 C14 C13 C12 1.72(18) . . . . ?
C9 C10 C11 C12 0.67(19) . . . . ?
C14 C9 C10 C11 0.46(18) . . . . ?
C14 C13 C12 C11 -0.59(19) . . . . ?
C10 C9 C14 C13 -1.65(18) . . . . ?
C10 C11 C12 C13 -0.61(19) . . . . ?
C6 C5 C7 N2 1.27(17) . . . . ?
C6 C5 C7 C8 179.18(11) . . . . ?
C6 C5 C4 C3 0.7(2) . . . . ?
C4 C5 C7 N2 -178.24(12) . . . . ?
C4 C5 C7 C8 -0.33(17) . . . . ?
C4 C5 C6 C1 -0.04(19) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C3 C2 C1 C6 0.9(2) . . . . ?

_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 1.164
_oxdiff_exptl_absorpt_empirical_full_min 0.760
