# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_0316_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2549586'
loop_
_audit_author_name
_audit_author_address
'Jia-Wei Li'
;Zhoukou Normal University
China
;
_audit_update_record             
;
2026-04-27 deposited with the CCDC.	2026-06-02 downloaded from the CCDC.
;
_audit_creation_date             2026-03-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N4'
_chemical_formula_sum            'C17 H16 N4'
_chemical_formula_weight         276.34
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8170(5)
_cell_length_b                   10.8205(10)
_cell_length_c                   11.6816(11)
_cell_angle_alpha                100.838(3)
_cell_angle_beta                 95.090(3)
_cell_angle_gamma                94.266(3)
_cell_volume                     716.19(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3664
_cell_measurement_temperature    198.0
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.79
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0630 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.4130.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22186
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_min         2.355
_diffrn_ambient_temperature      198.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2223
_reflns_number_total             2932
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.160
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.049
_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)+(0.0479P)²+0.1673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C15(H15), C13(H13), C14(H14), C6(H6), C7(H7), C3(H3),
 C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.7263(2) 0.25153(12) 0.28902(11) 0.0422(3) Uani 1 1 d . . . . .
N2 N 0.5683(2) 0.17134(12) 0.21624(11) 0.0426(3) Uani 1 1 d . . . . .
N4 N 0.7913(3) 0.05095(13) 0.28305(14) 0.0582(4) Uani 1 1 d . . . . .
N3 N 0.6044(3) 0.05126(13) 0.21145(14) 0.0586(4) Uani 1 1 d . . . . .
C11 C 0.1596(3) 0.39880(15) 0.11521(14) 0.0448(4) Uani 1 1 d . . . . .
H11A H 0.163050 0.371254 0.029669 0.054 Uiso 1 1 calc R U . . .
H11B H 0.014683 0.359450 0.136746 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1587(3) 0.54077(15) 0.14394(13) 0.0408(4) Uani 1 1 d . . . . .
C16 C 0.3295(3) 0.74899(16) 0.13508(15) 0.0492(4) Uani 1 1 d . . . . .
H16 H 0.448098 0.800742 0.111212 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3660(3) 0.35284(14) 0.17912(14) 0.0435(4) Uani 1 1 d . . . . .
H10A H 0.510095 0.394868 0.159372 0.052 Uiso 1 1 calc R U . . .
H10B H 0.359589 0.379167 0.264573 0.052 Uiso 1 1 calc R U . . .
C17 C 0.3302(3) 0.61910(15) 0.11029(14) 0.0454(4) Uani 1 1 d . . . . .
H17 H 0.450285 0.582435 0.069400 0.055 Uiso 1 1 calc R U . . .
C15 C 0.1560(3) 0.80364(16) 0.19470(14) 0.0490(4) Uani 1 1 d . . . . .
H15 H 0.154241 0.892927 0.211452 0.059 Uiso 1 1 calc R U . . .
C1 C 0.8635(3) 0.17295(14) 0.32938(14) 0.0423(4) Uani 1 1 d . . . . .
C13 C -0.0119(3) 0.59783(16) 0.20506(14) 0.0475(4) Uani 1 1 d . . . . .
H13 H -0.129125 0.546590 0.230483 0.057 Uiso 1 1 calc R U . . .
C2 C 1.0694(3) 0.21573(15) 0.41330(13) 0.0426(4) Uani 1 1 d . . . . .
C8 C 0.3778(3) 0.21287(15) 0.15089(14) 0.0432(4) Uani 1 1 d . . . . .
C14 C -0.0145(3) 0.72784(17) 0.22969(15) 0.0518(4) Uani 1 1 d . . . . .
H14 H -0.133927 0.764926 0.270787 0.062 Uiso 1 1 calc R U . . .
C6 C 1.3173(3) 0.38501(17) 0.53796(15) 0.0513(4) Uani 1 1 d . . . . .
H6 H 1.351165 0.472579 0.569990 0.062 Uiso 1 1 calc R U . . .
C7 C 1.1214(3) 0.34351(16) 0.45990(14) 0.0474(4) Uani 1 1 d . . . . .
H7 H 1.021936 0.402886 0.438136 0.057 Uiso 1 1 calc R U . . .
C3 C 1.2153(3) 0.12971(17) 0.44674(15) 0.0523(4) Uani 1 1 d . . . . .
H3 H 1.180591 0.041841 0.416366 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2393(4) 0.12858(18) 0.07493(17) 0.0585(5) Uani 1 1 d . . . . .
C5 C 1.4635(3) 0.29951(18) 0.56931(15) 0.0535(4) Uani 1 1 d . . . . .
H5 H 1.599595 0.328085 0.621612 0.064 Uiso 1 1 calc R U . . .
C4 C 1.4110(3) 0.17247(18) 0.52434(16) 0.0583(5) Uani 1 1 d . . . . .
H4 H 1.510399 0.113477 0.546898 0.070 Uiso 1 1 calc R U . . .
H9A H 0.112(3) 0.1561(18) 0.0282(17) 0.065(5) Uiso 1 1 d . . . . .
H9B H 0.266(3) 0.040(2) 0.0591(17) 0.067(6) 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
N1 N2 1.3363(17) . ?
N1 C1 1.3294(19) . ?
N2 N3 1.3232(18) . ?
N2 C8 1.437(2) . ?
N4 N3 1.312(2) . ?
N4 C1 1.349(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(2) . ?
C11 C10 1.521(2) . ?
C12 C17 1.392(2) . ?
C12 C13 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(2) . ?
C16 C15 1.383(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C8 1.496(2) . ?
C17 H17 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.378(2) . ?
C1 C2 1.465(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(2) . ?
C2 C7 1.387(2) . ?
C2 C3 1.391(2) . ?
C8 C9 1.315(2) . ?
C14 H14 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.385(2) . ?
C6 C5 1.379(2) . ?
C7 H7 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.383(2) . ?
C9 H9A 0.980(19) . ?
C9 H9B 0.97(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(3) . ?
C4 H4 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
C1 N1 N2 101.82(12) . . ?
N1 N2 C8 122.72(12) . . ?
N3 N2 N1 113.36(12) . . ?
N3 N2 C8 123.91(13) . . ?
N3 N4 C1 106.66(13) . . ?
N4 N3 N2 106.22(13) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C12 C11 C10 112.44(13) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C17 C12 C11 120.95(14) . . ?
C13 C12 C11 121.40(15) . . ?
C13 C12 C17 117.65(15) . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 119.92(16) . . ?
C15 C16 H16 120.0 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C8 C10 C11 114.39(13) . . ?
C8 C10 H10A 108.7 . . ?
C8 C10 H10B 108.7 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.39(15) . . ?
C16 C17 H17 119.3 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.63(16) . . ?
C14 C15 H15 120.2 . . ?
N1 C1 N4 111.94(14) . . ?
N1 C1 C2 123.27(14) . . ?
N4 C1 C2 124.78(14) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.31(16) . . ?
C14 C13 H13 119.3 . . ?
C7 C2 C1 119.98(14) . . ?
C7 C2 C3 119.20(15) . . ?
C3 C2 C1 120.82(15) . . ?
N2 C8 C10 113.28(13) . . ?
C9 C8 N2 118.95(15) . . ?
C9 C8 C10 127.77(16) . . ?
C15 C14 C13 120.10(16) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.16(17) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.39(15) . . ?
C6 C7 H7 119.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.81(17) . . ?
C4 C3 H3 120.1 . . ?
C8 C9 H9A 119.6(11) . . ?
C8 C9 H9B 121.9(11) . . ?
H9A C9 H9B 118.3(16) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.61(16) . . ?
C4 C5 H5 120.2 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.81(16) . . ?
C5 C4 H4 119.6 . . ?

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
N1 N2 N3 N4 0.09(19) . . . . ?
N1 N2 C8 C10 -4.1(2) . . . . ?
N1 N2 C8 C9 175.23(16) . . . . ?
N1 C1 C2 C7 3.9(2) . . . . ?
N1 C1 C2 C3 -175.76(15) . . . . ?
N2 N1 C1 N4 -0.05(17) . . . . ?
N2 N1 C1 C2 179.37(14) . . . . ?
N4 C1 C2 C7 -176.79(16) . . . . ?
N4 C1 C2 C3 3.6(3) . . . . ?
N3 N2 C8 C10 175.43(15) . . . . ?
N3 N2 C8 C9 -5.3(3) . . . . ?
N3 N4 C1 N1 0.1(2) . . . . ?
N3 N4 C1 C2 -179.31(15) . . . . ?
C11 C12 C17 C16 179.32(14) . . . . ?
C11 C12 C13 C14 -178.97(15) . . . . ?
C11 C10 C8 N2 -177.39(13) . . . . ?
C11 C10 C8 C9 3.4(3) . . . . ?
C12 C11 C10 C8 -178.42(13) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C16 C15 C14 C13 -0.1(2) . . . . ?
C10 C11 C12 C17 66.12(19) . . . . ?
C10 C11 C12 C13 -113.59(16) . . . . ?
C17 C12 C13 C14 1.3(2) . . . . ?
C17 C16 C15 C14 0.4(2) . . . . ?
C15 C16 C17 C12 0.1(2) . . . . ?
C1 N1 N2 N3 -0.03(17) . . . . ?
C1 N1 N2 C8 179.51(14) . . . . ?
C1 N4 N3 N2 -0.11(19) . . . . ?
C1 C2 C7 C6 -179.06(15) . . . . ?
C1 C2 C3 C4 178.76(16) . . . . ?
C13 C12 C17 C16 -1.0(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C8 N2 N3 N4 -179.45(14) . . . . ?
C6 C5 C4 C3 1.0(3) . . . . ?
C7 C2 C3 C4 -0.9(3) . . . . ?
C7 C6 C5 C4 -1.3(3) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
