# 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_mo_230926b_0m
_database_code_depnum_ccdc_archive 'CCDC 2500510'
loop_
_audit_author_name
_audit_author_address
'Can Wang'
;Wuhan Institute of Technology
China
;
_audit_update_record             
;
2025-11-05 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_audit_creation_date             2025-09-22
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 N4'
_chemical_formula_sum            'C15 H10 N4'
_chemical_formula_weight         246.27
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.732(2)
_cell_length_b                   8.394(3)
_cell_length_c                   23.847(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.848(5)
_cell_angle_gamma                90
_cell_volume                     1147.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5356
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.52
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.4852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            11544
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.008
_diffrn_reflns_theta_min         1.708
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2743
_reflns_number_total             3690
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3690
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+0.2851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1602
_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: 
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), 
 C14(H14), C15(H15) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
; 
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.030 
;
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 1.0548(2) 0.34490(15) 0.88761(5) 0.0369(3) Uani 1 1 d . . . . .
C2 C 0.9626(2) 0.33147(15) 0.94135(5) 0.0360(3) Uani 1 1 d . . . . .
C3 C 0.7391(2) 0.35319(18) 1.01873(6) 0.0456(3) Uani 1 1 d . . . . .
H3 H 0.6092 0.3941 1.0367 0.055 Uiso 1 1 calc R . . . .
C4 C 0.8894(2) 0.24755(17) 1.05024(6) 0.0421(3) Uani 1 1 d . . . . .
C5 C 1.0882(2) 0.18664(15) 1.02475(5) 0.0386(3) Uani 1 1 d . . . . .
C6 C 1.2451(3) 0.08774(18) 1.05304(6) 0.0479(3) Uani 1 1 d . . . . .
H6 H 1.3769 0.0487 1.0354 0.057 Uiso 1 1 calc R . . . .
C7 C 1.1995(3) 0.0493(2) 1.10799(7) 0.0553(4) Uani 1 1 d . . . . .
H7 H 1.3024 -0.0166 1.1276 0.066 Uiso 1 1 calc R . . . .
C8 C 1.0029(3) 0.1073(2) 1.13457(7) 0.0592(5) Uani 1 1 d . . . . .
H8 H 0.9758 0.0796 1.1717 0.071 Uiso 1 1 calc R . . . .
C9 C 0.8479(3) 0.2050(2) 1.10662(6) 0.0526(4) Uani 1 1 d . . . . .
H9 H 0.7165 0.2431 1.1247 0.063 Uiso 1 1 calc R . . . .
C10 C 0.9751(2) 0.43780(15) 0.83911(5) 0.0370(3) Uani 1 1 d . . . . .
C11 C 0.7581(3) 0.51427(19) 0.83848(6) 0.0462(3) Uani 1 1 d . . . . .
H11 H 0.6581 0.5021 0.8685 0.055 Uiso 1 1 calc R . . . .
C12 C 0.6922(3) 0.6083(2) 0.79311(7) 0.0516(4) Uani 1 1 d . . . . .
H12 H 0.5481 0.6592 0.7931 0.062 Uiso 1 1 calc R . . . .
C13 C 0.8374(3) 0.62705(19) 0.74818(6) 0.0520(4) Uani 1 1 d . . . . .
H13 H 0.7928 0.6917 0.7182 0.062 Uiso 1 1 calc R . . . .
C14 C 1.0493(3) 0.5496(2) 0.74774(6) 0.0548(4) Uani 1 1 d . . . . .
H14 H 1.1465 0.5606 0.7171 0.066 Uiso 1 1 calc R . . . .
C15 C 1.1183(3) 0.45507(19) 0.79282(6) 0.0468(3) Uani 1 1 d . . . . .
H15 H 1.2614 0.4029 0.7921 0.056 Uiso 1 1 calc R . . . .
N1 N 1.2540(2) 0.25540(15) 0.88637(5) 0.0442(3) Uani 1 1 d . . . . .
N2 N 1.2935(2) 0.18623(15) 0.93535(5) 0.0453(3) Uani 1 1 d . . . . .
N3 N 1.11696(19) 0.23219(13) 0.96891(4) 0.0372(2) Uani 1 1 d . . . . .
N4 N 0.7720(2) 0.39571(14) 0.96673(5) 0.0430(3) Uani 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
C1 C2 1.3981(18) . ?
C1 C10 1.4625(18) . ?
C1 N1 1.3674(18) . ?
C2 N3 1.3754(17) . ?
C2 N4 1.3675(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.440(2) . ?
C3 N4 1.3068(19) . ?
C4 C5 1.396(2) . ?
C4 C9 1.415(2) . ?
C5 C6 1.391(2) . ?
C5 N3 1.3975(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.399(2) . ?
C10 C15 1.3932(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(2) . ?
C15 H15 0.9300 . ?
N1 N2 1.3209(17) . ?
N2 N3 1.3555(16) . ?

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
C2 C1 C10 130.55(12) . . ?
N1 C1 C2 107.60(11) . . ?
N1 C1 C10 121.81(12) . . ?
N3 C2 C1 103.76(11) . . ?
N4 C2 C1 133.56(12) . . ?
N4 C2 N3 122.68(12) . . ?
C4 C3 H3 117.6 . . ?
N4 C3 H3 117.6 . . ?
N4 C3 C4 124.73(13) . . ?
C5 C4 C3 118.95(13) . . ?
C5 C4 C9 118.11(14) . . ?
C9 C4 C3 122.93(14) . . ?
C4 C5 N3 115.03(13) . . ?
C6 C5 C4 122.22(13) . . ?
C6 C5 N3 122.75(13) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 C5 118.07(16) . . ?
C7 C6 H6 121.0 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.23(16) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.70(15) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 H9 120.2 . . ?
C8 C9 C4 119.67(16) . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C1 121.35(12) . . ?
C15 C10 C1 120.08(12) . . ?
C15 C10 C11 118.55(13) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.08(14) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.78(15) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.70(14) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.32(15) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.54(14) . . ?
C14 C15 H15 119.7 . . ?
N2 N1 C1 110.78(12) . . ?
N1 N2 N3 106.10(11) . . ?
C2 N3 C5 122.48(12) . . ?
N2 N3 C2 111.77(11) . . ?
N2 N3 C5 125.75(12) . . ?
C3 N4 C2 116.08(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
