# 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_exp_4053
_database_code_depnum_ccdc_archive 'CCDC 2544364'
loop_
_audit_author_name
_audit_author_address
'Xuhao Zhang'
;Shandong Normal University
China
;
_audit_update_record             
;
2026-04-07 deposited with the CCDC.	2026-05-13 downloaded from the CCDC.
;
_audit_creation_date             2026-04-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.03.20 svn.r2bc28608 for OlexSys, GUI svn.r7530)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H18 N4 O2'
_chemical_formula_sum            'C28 H18 N4 O2'
_chemical_formula_weight         442.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'

_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                   16.0275(13)
_cell_length_b                   14.7197(16)
_cell_length_c                   18.5097(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4366.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3490
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      27.7690
_cell_measurement_theta_min      3.7350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36100
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.401
_diffrn_reflns_theta_min         3.363
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  47.00   1.00    7.50    --  -18.72  57.00 150.00   80
  2  ω    -29.00  11.00   1.00    7.50    --  -18.72 -77.00  30.00   40
  3  ω    -25.00   9.00   1.00    7.50    --  -18.72 -77.00 150.00   34
  4  ω    -49.00  41.00   1.00    7.50    --   19.35 -57.00-120.00   90
  5  ω     39.00  64.00   1.00    7.50    --   19.35 178.00 -60.00   25
  6  ω     55.00  81.00   1.00    7.50    --   19.35  57.00 -60.00   26
  7  ω     -2.00  88.00   1.00    7.50    --   19.35  57.00  30.00   90
  8  ω     18.00  43.00   1.00    7.50    --   19.35 -77.00 -90.00   25
  9  ω     40.00  67.00   1.00    7.50    --   19.35 178.00-150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0071692000
_diffrn_orient_matrix_UB_12      -0.0414677000
_diffrn_orient_matrix_UB_13      0.0185404000
_diffrn_orient_matrix_UB_21      -0.0281477000
_diffrn_orient_matrix_UB_22      0.0136805000
_diffrn_orient_matrix_UB_23      0.0274877000
_diffrn_orient_matrix_UB_31      -0.0334111000
_diffrn_orient_matrix_UB_32      -0.0204386000
_diffrn_orient_matrix_UB_33      -0.0191459000
_diffrn_oxdiff_digest_hkl        
;
01a2ead0e6012237e5875cc5537b407c077934
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2638
_reflns_number_total             5533
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1512
_refine_ls_R_factor_gt           0.0712
_refine_ls_restrained_S_all      1.032
_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)+(0.1109P)²+1.1235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.2517
_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:
 C8(H8), C33(H33), C14(H14), C26(H26), C32(H32), C7(H7), C29(H29), C17(H17),
 C5(H5), C15(H15), C22(H22), C16(H16), C6(H6), C31(H31), C30(H30), C25(H25),
 C24(H24), C23(H23)
;
_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
O27 O 0.64599(11) 0.35117(14) 0.76162(10) 0.0465(5) Uani 1 1 d . . . . .
O34 O 0.59288(11) 0.14528(14) 0.75896(10) 0.0462(5) Uani 1 1 d . . . . .
N11 N 0.66437(11) 0.25696(14) 0.66518(10) 0.0306(5) Uani 1 1 d . . . . .
N1 N 0.57837(11) 0.24129(14) 0.66352(10) 0.0302(5) Uani 1 1 d . . . . .
N3 N 0.45195(14) 0.26370(16) 0.60148(12) 0.0440(6) Uani 1 1 d . . . . .
N19 N 0.79439(13) 0.23315(16) 0.60983(13) 0.0450(6) Uani 1 1 d . . . . .
C13 C 0.78274(15) 0.33548(18) 0.71407(14) 0.0369(6) Uani 1 1 d . . . . .
C2 C 0.52924(15) 0.28417(17) 0.61070(13) 0.0339(6) Uani 1 1 d . . . . .
C20 C 0.71600(15) 0.21513(17) 0.61430(13) 0.0352(6) Uani 1 1 d . . . . .
C10 C 0.54670(15) 0.17974(18) 0.71483(13) 0.0343(6) Uani 1 1 d . . . . .
C12 C 0.69395(15) 0.31674(18) 0.71885(13) 0.0352(6) Uani 1 1 d . . . . .
C28 C 0.56745(16) 0.35499(18) 0.56361(13) 0.0370(6) Uani 1 1 d . . . . .
C9 C 0.45803(15) 0.16103(18) 0.70542(14) 0.0369(6) Uani 1 1 d . . . . .
C21 C 0.67828(16) 0.14999(18) 0.56274(14) 0.0382(6) Uani 1 1 d . . . . .
C4 C 0.41494(16) 0.20118(19) 0.64868(16) 0.0408(7) Uani 1 1 d . . . . .
C18 C 0.82908(16) 0.29524(19) 0.65927(16) 0.0424(7) Uani 1 1 d . . . . .
C8 C 0.41695(17) 0.10229(19) 0.75255(16) 0.0449(7) Uani 1 1 d . . . . .
H8 H 0.446851 0.074923 0.791154 0.054 Uiso 1 1 calc R U . . .
C33 C 0.60463(16) 0.43251(19) 0.59244(15) 0.0409(7) Uani 1 1 d . . . . .
H33 H 0.611280 0.438240 0.643235 0.049 Uiso 1 1 calc R U . . .
C14 C 0.82131(17) 0.39540(19) 0.76270(16) 0.0460(7) Uani 1 1 d . . . . .
H14 H 0.789370 0.422539 0.800156 0.055 Uiso 1 1 calc R U . . .
C26 C 0.63992(18) 0.06983(19) 0.58459(15) 0.0460(7) Uani 1 1 d . . . . .
H26 H 0.634682 0.056104 0.634536 0.055 Uiso 1 1 calc R U . . .
C32 C 0.63193(19) 0.5013(2) 0.54704(18) 0.0530(8) Uani 1 1 d . . . . .
H32 H 0.656955 0.554135 0.567004 0.064 Uiso 1 1 calc R U . . .
C7 C 0.33389(18) 0.0837(2) 0.74370(18) 0.0524(8) Uani 1 1 d . . . . .
H7 H 0.306005 0.044221 0.776365 0.063 Uiso 1 1 calc R U . . .
C29 C 0.5581(2) 0.3483(2) 0.48942(15) 0.0520(8) Uani 1 1 d . . . . .
H29 H 0.531556 0.296574 0.469088 0.062 Uiso 1 1 calc R U . . .
C17 C 0.91459(18) 0.3161(2) 0.6539(2) 0.0599(9) Uani 1 1 d . . . . .
H17 H 0.947726 0.289138 0.617202 0.072 Uiso 1 1 calc R U . . .
C5 C 0.32984(18) 0.1802(2) 0.63977(19) 0.0562(9) Uani 1 1 d . . . . .
H5 H 0.299421 0.206176 0.600855 0.067 Uiso 1 1 calc R U . . .
C15 C 0.90401(19) 0.4150(2) 0.75673(19) 0.0553(9) Uani 1 1 d . . . . .
H15 H 0.929865 0.455365 0.789936 0.066 Uiso 1 1 calc R U . . .
C22 C 0.6857(2) 0.1672(2) 0.48970(16) 0.0572(9) Uani 1 1 d . . . . .
H22 H 0.712928 0.221006 0.473931 0.069 Uiso 1 1 calc R U . . .
C16 C 0.94979(19) 0.3758(2) 0.7021(2) 0.0640(10) Uani 1 1 d . . . . .
H16 H 1.007298 0.390383 0.697662 0.077 Uiso 1 1 calc R U . . .
C6 C 0.29085(18) 0.1227(2) 0.6868(2) 0.0609(9) Uani 1 1 d . . . . .
H6 H 0.233338 0.109346 0.680392 0.073 Uiso 1 1 calc R U . . .
C31 C 0.62319(19) 0.4938(3) 0.47381(19) 0.0621(9) Uani 1 1 d . . . . .
H31 H 0.641767 0.541339 0.443090 0.075 Uiso 1 1 calc R U . . .
C30 C 0.5873(2) 0.4169(3) 0.44469(17) 0.0642(10) Uani 1 1 d . . . . .
H30 H 0.582584 0.410904 0.393749 0.077 Uiso 1 1 calc R U . . .
C25 C 0.6097(2) 0.0106(2) 0.53362(19) 0.0644(9) Uani 1 1 d . . . . .
H25 H 0.583255 -0.043977 0.548606 0.077 Uiso 1 1 calc R U . . .
C24 C 0.6171(2) 0.0295(3) 0.4611(2) 0.0729(11) Uani 1 1 d . . . . .
H24 H 0.596244 -0.012129 0.426243 0.087 Uiso 1 1 calc R U . . .
C23 C 0.6543(2) 0.1075(3) 0.43948(18) 0.0719(11) Uani 1 1 d . . . . .
H23 H 0.658661 0.121001 0.389442 0.086 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
O27 C12 1.214(3) . ?
O34 C10 1.213(3) . ?
N11 N1 1.398(3) . ?
N11 C20 1.397(3) . ?
N11 C12 1.409(3) . ?
N1 C2 1.405(3) . ?
N1 C10 1.407(3) . ?
N3 C2 1.286(3) . ?
N3 C4 1.401(3) . ?
N19 C20 1.287(3) . ?
N19 C18 1.408(4) . ?
C13 C12 1.452(3) . ?
C13 C18 1.390(4) . ?
C13 C14 1.404(4) . ?
C2 C28 1.491(4) . ?
C20 C21 1.482(4) . ?
C10 C9 1.458(3) . ?
C28 C33 1.394(4) . ?
C28 C29 1.385(4) . ?
C9 C4 1.389(4) . ?
C9 C8 1.394(4) . ?
C21 C26 1.391(4) . ?
C21 C22 1.381(4) . ?
C4 C5 1.408(4) . ?
C18 C17 1.408(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.369(4) . ?
C33 H33 0.9500 . ?
C33 C32 1.387(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.361(4) . ?
C26 H26 0.9500 . ?
C26 C25 1.373(4) . ?
C32 H32 0.9500 . ?
C32 C31 1.367(5) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.373(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.366(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.375(5) . ?
C16 H16 0.9500 . ?
C6 H6 0.9500 . ?
C31 H31 0.9500 . ?
C31 C30 1.379(5) . ?
C30 H30 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.377(5) . ?
C24 H24 0.9500 . ?
C24 C23 1.354(5) . ?
C23 H23 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
N1 N11 C12 116.76(19) . . ?
C20 N11 N1 119.78(19) . . ?
C20 N11 C12 123.5(2) . . ?
N11 N1 C2 119.58(19) . . ?
N11 N1 C10 116.56(18) . . ?
C2 N1 C10 123.82(19) . . ?
C2 N3 C4 118.6(2) . . ?
C20 N19 C18 118.5(2) . . ?
C18 C13 C12 119.2(2) . . ?
C18 C13 C14 120.0(2) . . ?
C14 C13 C12 120.8(2) . . ?
N1 C2 C28 119.4(2) . . ?
N3 C2 N1 121.8(2) . . ?
N3 C2 C28 118.8(2) . . ?
N11 C20 C21 118.5(2) . . ?
N19 C20 N11 122.1(2) . . ?
N19 C20 C21 119.4(2) . . ?
O34 C10 N1 120.2(2) . . ?
O34 C10 C9 126.6(2) . . ?
N1 C10 C9 113.1(2) . . ?
O27 C12 N11 120.5(2) . . ?
O27 C12 C13 125.5(2) . . ?
N11 C12 C13 113.9(2) . . ?
C33 C28 C2 121.6(2) . . ?
C29 C28 C2 119.1(2) . . ?
C29 C28 C33 119.0(3) . . ?
C4 C9 C10 119.6(2) . . ?
C4 C9 C8 120.2(2) . . ?
C8 C9 C10 120.2(2) . . ?
C26 C21 C20 122.8(2) . . ?
C22 C21 C20 118.5(3) . . ?
C22 C21 C26 118.6(3) . . ?
N3 C4 C5 118.8(3) . . ?
C9 C4 N3 122.7(2) . . ?
C9 C4 C5 118.5(3) . . ?
C13 C18 N19 122.7(2) . . ?
C13 C18 C17 118.6(3) . . ?
C17 C18 N19 118.7(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C28 C33 H33 120.0 . . ?
C32 C33 C28 120.0(3) . . ?
C32 C33 H33 120.0 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C21 C26 H26 120.2 . . ?
C25 C26 C21 119.7(3) . . ?
C25 C26 H26 120.2 . . ?
C33 C32 H32 119.7 . . ?
C31 C32 C33 120.6(3) . . ?
C31 C32 H32 119.7 . . ?
C8 C7 H7 120.2 . . ?
C8 C7 C6 119.5(3) . . ?
C6 C7 H7 120.2 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C18 C17 H17 120.2 . . ?
C16 C17 C18 119.6(3) . . ?
C16 C17 H17 120.2 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C32 C31 H31 120.1 . . ?
C32 C31 C30 119.8(3) . . ?
C30 C31 H31 120.1 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.3(3) . . ?
C31 C30 H30 119.8 . . ?
C26 C25 H25 119.6 . . ?
C26 C25 C24 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C25 C24 H24 120.1 . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.9 . . ?

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
O34 C10 C9 C4 -175.1(3) . . . . ?
O34 C10 C9 C8 4.0(4) . . . . ?
N11 N1 C2 N3 171.5(2) . . . . ?
N11 N1 C2 C28 -8.1(3) . . . . ?
N11 N1 C10 O34 2.2(3) . . . . ?
N11 N1 C10 C9 -174.9(2) . . . . ?
N11 C20 C21 C26 -62.3(4) . . . . ?
N11 C20 C21 C22 121.4(3) . . . . ?
N1 N11 C20 N19 174.2(2) . . . . ?
N1 N11 C20 C21 -4.1(3) . . . . ?
N1 N11 C12 O27 1.0(4) . . . . ?
N1 N11 C12 C13 -175.5(2) . . . . ?
N1 C2 C28 C33 -57.8(3) . . . . ?
N1 C2 C28 C29 129.1(3) . . . . ?
N1 C10 C9 C4 1.7(3) . . . . ?
N1 C10 C9 C8 -179.2(2) . . . . ?
N3 C2 C28 C33 122.6(3) . . . . ?
N3 C2 C28 C29 -50.5(4) . . . . ?
N3 C4 C5 C6 -177.0(3) . . . . ?
N19 C20 C21 C26 119.4(3) . . . . ?
N19 C20 C21 C22 -56.9(4) . . . . ?
N19 C18 C17 C16 -179.3(3) . . . . ?
C13 C18 C17 C16 -0.5(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C2 N1 C10 O34 -180.0(2) . . . . ?
C2 N1 C10 C9 3.0(3) . . . . ?
C2 N3 C4 C9 0.6(4) . . . . ?
C2 N3 C4 C5 178.5(3) . . . . ?
C2 C28 C33 C32 -173.4(2) . . . . ?
C2 C28 C29 C30 174.9(3) . . . . ?
C20 N11 N1 C2 -75.9(3) . . . . ?
C20 N11 N1 C10 102.1(2) . . . . ?
C20 N11 C12 O27 179.9(2) . . . . ?
C20 N11 C12 C13 3.5(3) . . . . ?
C20 N19 C18 C13 2.2(4) . . . . ?
C20 N19 C18 C17 -179.1(3) . . . . ?
C20 C21 C26 C25 -177.0(3) . . . . ?
C20 C21 C22 C23 177.9(3) . . . . ?
C10 N1 C2 N3 -6.3(4) . . . . ?
C10 N1 C2 C28 174.1(2) . . . . ?
C10 C9 C4 N3 -3.6(4) . . . . ?
C10 C9 C4 C5 178.5(3) . . . . ?
C10 C9 C8 C7 -179.4(3) . . . . ?
C12 N11 N1 C2 103.1(2) . . . . ?
C12 N11 N1 C10 -78.9(3) . . . . ?
C12 N11 C20 N19 -4.8(4) . . . . ?
C12 N11 C20 C21 177.0(2) . . . . ?
C12 C13 C18 N19 -3.2(4) . . . . ?
C12 C13 C18 C17 178.1(3) . . . . ?
C12 C13 C14 C15 -178.0(3) . . . . ?
C28 C33 C32 C31 -0.4(4) . . . . ?
C28 C29 C30 C31 -2.4(5) . . . . ?
C9 C4 C5 C6 1.0(5) . . . . ?
C9 C8 C7 C6 0.9(4) . . . . ?
C21 C26 C25 C24 0.3(5) . . . . ?
C21 C22 C23 C24 -1.6(5) . . . . ?
C4 N3 C2 N1 4.2(4) . . . . ?
C4 N3 C2 C28 -176.2(2) . . . . ?
C4 C9 C8 C7 -0.2(4) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C18 N19 C20 N11 1.7(4) . . . . ?
C18 N19 C20 C21 180.0(2) . . . . ?
C18 C13 C12 O27 -175.9(3) . . . . ?
C18 C13 C12 N11 0.3(3) . . . . ?
C18 C13 C14 C15 0.2(4) . . . . ?
C18 C17 C16 C15 1.1(5) . . . . ?
C8 C9 C4 N3 177.2(2) . . . . ?
C8 C9 C4 C5 -0.7(4) . . . . ?
C8 C7 C6 C5 -0.6(5) . . . . ?
C33 C28 C29 C30 1.6(4) . . . . ?
C33 C32 C31 C30 -0.4(5) . . . . ?
C14 C13 C12 O27 2.3(4) . . . . ?
C14 C13 C12 N11 178.6(2) . . . . ?
C14 C13 C18 N19 178.6(2) . . . . ?
C14 C13 C18 C17 -0.1(4) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C26 C21 C22 C23 1.4(5) . . . . ?
C26 C25 C24 C23 -0.4(6) . . . . ?
C32 C31 C30 C29 1.7(5) . . . . ?
C29 C28 C33 C32 -0.3(4) . . . . ?
C22 C21 C26 C25 -0.8(4) . . . . ?
C25 C24 C23 C22 1.0(6) . . . . ?


_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 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.514
####################################################################### 
# 
# 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_exp_4017
_database_code_depnum_ccdc_archive 'CCDC 2544533'
loop_
_audit_author_name
_audit_author_address
'Xuhao Zhang'
;Shandong Normal university
China
;
_audit_update_record             
;
2026-04-08 deposited with the CCDC.	2026-05-13 downloaded from the CCDC.
;
_audit_creation_date             2026-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.03.18 svn.r0db52de7 for OlexSys, GUI svn.r7521)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N2 O'
_chemical_formula_sum            'C7 H7 N2 O'
_chemical_formula_weight         135.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.926(3)
_cell_length_b                   5.3094(11)
_cell_length_c                   9.688(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.73(3)
_cell_angle_gamma                90
_cell_volume                     617.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    951
_cell_measurement_temperature    294.76(11)
_cell_measurement_theta_max      27.7780
_cell_measurement_theta_min      4.1750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.397
_diffrn_reflns_theta_min         4.197
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.76(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  11.00   1.00   10.00    --  -18.72 -77.00  30.00   51
  2  ω    -39.00   0.00   1.00   10.00    --  -18.72 -77.00 -90.00   39
  3  ω    -26.00   6.00   1.00   10.00    --  -18.72 -77.00 150.00   32
  4  ω     10.00  88.00   1.00   10.00    --   19.35  57.00 150.00   78
  5  ω     -3.00  83.00   1.00   10.00    --   19.35  37.00  30.00   86
  6  ω    -53.00  45.00   1.00   10.00    --   19.35 -37.00-150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0108946000
_diffrn_orient_matrix_UB_12      -0.0449471000
_diffrn_orient_matrix_UB_13      -0.0728871000
_diffrn_orient_matrix_UB_21      0.0470736000
_diffrn_orient_matrix_UB_22      -0.0805091000
_diffrn_orient_matrix_UB_23      0.0276507000
_diffrn_orient_matrix_UB_31      -0.0340622000
_diffrn_orient_matrix_UB_32      -0.0967989000
_diffrn_orient_matrix_UB_33      0.0108826000
_diffrn_oxdiff_digest_hkl        
;
01d7b2b123beb2920e74624fc80d834b332220
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1037
_reflns_number_total             1492
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      0.858
_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)+(0.1102P)²+0.5478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N9(H9), C2(H2), C5(H5), C3(H3), 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
N10 N 0.67579(19) 0.2967(4) 0.7790(2) 0.0380(5) Uani 1 1 d . . . . .
O8 O 0.54782(14) 0.7276(3) 0.70464(19) 0.0431(5) Uani 1 1 d . . . . .
N9 N 0.54560(15) 0.9289(4) 0.50188(19) 0.0388(5) Uani 1 1 d . . . . .
H9 H 0.573501 0.949160 0.434664 0.047 Uiso 1 1 calc R U . . .
C6 C 0.73212(16) 0.4132(4) 0.7027(2) 0.0293(5) Uani 1 1 d . . . . .
C7 C 0.58973(16) 0.7609(4) 0.6102(2) 0.0285(5) Uani 1 1 d . . . . .
C1 C 0.69363(16) 0.6320(4) 0.6162(2) 0.0281(5) Uani 1 1 d . . . . .
C2 C 0.75884(18) 0.7374(4) 0.5434(2) 0.0344(5) Uani 1 1 d . . . . .
H2 H 0.733949 0.882565 0.487185 0.041 Uiso 1 1 calc R U . . .
C5 C 0.83550(18) 0.3123(5) 0.7118(3) 0.0384(6) Uani 1 1 d . . . . .
H5 H 0.862579 0.168779 0.768779 0.046 Uiso 1 1 calc R U . . .
C3 C 0.85896(19) 0.6326(5) 0.5526(3) 0.0417(6) Uani 1 1 d . . . . .
H3 H 0.900164 0.703527 0.501530 0.050 Uiso 1 1 calc R U . . .
C4 C 0.89666(18) 0.4201(5) 0.6392(3) 0.0442(6) Uani 1 1 d . . . . .
H4 H 0.964689 0.349640 0.647985 0.053 Uiso 1 1 calc R U . . .
H10A H 0.608(3) 0.346(7) 0.765(4) 0.070(10) Uiso 1 1 d . . . . .
H10B H 0.700(2) 0.148(6) 0.815(3) 0.056(8) 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
N10 C6 1.363(3) . ?
N10 H10A 0.88(4) . ?
N10 H10B 0.87(3) . ?
O8 C7 1.236(3) . ?
N9 N9 1.389(3) 3_676 ?
N9 H9 0.8600 . ?
N9 C7 1.334(3) . ?
C6 C1 1.411(3) . ?
C6 C5 1.412(3) . ?
C7 C1 1.489(3) . ?
C1 C2 1.400(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9300 . ?

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
C6 N10 H10A 119(2) . . ?
C6 N10 H10B 116.2(19) . . ?
H10A N10 H10B 122(3) . . ?
N9 N9 H9 120.1 3_676 . ?
C7 N9 N9 119.7(2) . 3_676 ?
C7 N9 H9 120.1 . . ?
N10 C6 C1 123.64(19) . . ?
N10 C6 C5 118.5(2) . . ?
C1 C6 C5 117.8(2) . . ?
O8 C7 N9 120.05(19) . . ?
O8 C7 C1 122.79(19) . . ?
N9 C7 C1 117.04(18) . . ?
C6 C1 C7 121.06(18) . . ?
C2 C1 C6 118.84(18) . . ?
C2 C1 C7 119.96(19) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.1(2) . . ?
C3 C2 H2 118.9 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(2) . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?

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
N10 C6 C1 C7 3.7(3) . . . . ?
N10 C6 C1 C2 179.4(2) . . . . ?
N10 C6 C5 C4 -179.5(2) . . . . ?
O8 C7 C1 C6 18.8(3) . . . . ?
O8 C7 C1 C2 -156.8(2) . . . . ?
N9 N9 C7 O8 1.8(4) 3_676 . . . ?
N9 N9 C7 C1 -174.4(2) 3_676 . . . ?
N9 C7 C1 C6 -165.13(19) . . . . ?
N9 C7 C1 C2 19.3(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C5 C4 C3 -0.4(4) . . . . ?
C7 C1 C2 C3 176.3(2) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C5 C6 C1 C7 -175.33(19) . . . . ?
C5 C6 C1 C2 0.3(3) . . . . ?


_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 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.712
