# Supplementary Information (SI) for RSC Advances.
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 2423210'
loop_
_audit_author_name
_audit_author_address
'Xianggao Meng'
;Central China Normal University
China
;
_audit_update_record             
;
2025-02-12 deposited with the CCDC.	2025-08-05 downloaded from the CCDC.
;
_audit_creation_date             2024-07-12
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_chemical_name_common            ?
_chemical_name_systematic        
; 
 ? 
;
_chemical_formula_moiety         'C21 H16 N4 O2'
_chemical_formula_sum            'C21 H16 N4 O2'
_chemical_formula_weight         356.38
_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'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.613(3)
_cell_length_b                   10.293(2)
_cell_length_c                   11.665(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.435(4)
_cell_angle_gamma                90.00
_cell_volume                     1749.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4033
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.42
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
; 
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14808
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         1.40
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2889
_reflns_number_total             4127
_reflns_threshold_expression     >2sigma(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  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0777P)²+0.2247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1441
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), 
 C18(H18), C19(H19), C20(H20), C21(H21) 
2.b Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C) 
2.c Idealised tetrahedral OH refined as rotating group: 
 O2(H2A) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_special_details      
; 
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.033 
;
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.35245(14) 0.4122(2) 0.4820(2) 0.0710(6) Uani 1 d . . .
H1A H 0.2962 0.3660 0.4634 0.106 Uiso 1 calc . . GR
H1B H 0.3678 0.4620 0.4166 0.106 Uiso 1 calc . . GR
H1C H 0.3451 0.4696 0.5456 0.106 Uiso 1 calc . . GR
C2 C 0.50028(11) 0.29843(16) 0.45543(14) 0.0474(4) Uani 1 d . . .
H2 H 0.5169 0.3422 0.3904 0.057 Uiso 1 calc . . R
C3 C 0.54759(10) 0.19767(15) 0.51257(12) 0.0406(3) Uani 1 d . . .
C4 C 0.49304(11) 0.16455(16) 0.60478(12) 0.0437(4) Uani 1 d . . .
C5 C 0.58367(12) -0.00619(17) 0.66332(13) 0.0462(4) Uani 1 d . . .
H5 H 0.5978 -0.0759 0.7123 0.055 Uiso 1 calc . . R
C6 C 0.64215(11) 0.01979(15) 0.57482(12) 0.0417(4) Uani 1 d . . .
C7 C 0.62498(10) 0.12052(15) 0.49969(11) 0.0385(3) Uani 1 d . . .
C8 C 0.69569(10) 0.12461(15) 0.41044(12) 0.0398(3) Uani 1 d . . .
C9 C 0.72369(11) -0.05248(16) 0.54095(13) 0.0446(4) Uani 1 d . . .
C10 C 0.82700(10) -0.03450(16) 0.38305(13) 0.0433(4) Uani 1 d . . .
C11 C 0.91020(13) 0.0288(2) 0.39002(19) 0.0651(5) Uani 1 d . . .
H11 H 0.9187 0.1028 0.4353 0.078 Uiso 1 calc . . R
C12 C 0.98112(14) -0.0175(2) 0.3299(2) 0.0739(6) Uani 1 d . . .
H12 H 1.0369 0.0265 0.3338 0.089 Uiso 1 calc . . R
C13 C 0.96988(13) -0.1277(2) 0.26454(17) 0.0617(5) Uani 1 d . . .
H13 H 1.0184 -0.1605 0.2264 0.074 Uiso 1 calc . . R
C14 C 0.88705(14) -0.1887(2) 0.2559(2) 0.0700(6) Uani 1 d . . .
H14 H 0.8788 -0.2622 0.2099 0.084 Uiso 1 calc . . R
C15 C 0.81473(13) -0.14274(19) 0.31500(18) 0.0611(5) Uani 1 d . . .
H15 H 0.7583 -0.1851 0.3085 0.073 Uiso 1 calc . . R
C16 C 0.75126(10) 0.24984(15) 0.41820(12) 0.0402(3) Uani 1 d . . .
C17 C 0.80156(14) 0.28157(19) 0.52032(14) 0.0579(5) Uani 1 d . . .
H17 H 0.8005 0.2262 0.5832 0.070 Uiso 1 calc . . R
C18 C 0.85269(14) 0.3933(2) 0.52970(17) 0.0646(5) Uani 1 d . . .
H18 H 0.8859 0.4132 0.5987 0.077 Uiso 1 calc . . R
C19 C 0.85492(13) 0.47620(19) 0.43703(19) 0.0628(5) Uani 1 d . . .
H19 H 0.8900 0.5517 0.4429 0.075 Uiso 1 calc . . R
C20 C 0.80507(13) 0.44623(19) 0.33641(17) 0.0596(5) Uani 1 d . . .
H20 H 0.8061 0.5020 0.2738 0.072 Uiso 1 calc . . R
C21 C 0.75316(11) 0.33375(16) 0.32674(14) 0.0469(4) Uani 1 d . . .
H21 H 0.7193 0.3148 0.2579 0.056 Uiso 1 calc . . R
N1 N 0.42579(10) 0.31981(14) 0.51311(12) 0.0529(4) Uani 1 d . . .
N2 N 0.41844(10) 0.24089(15) 0.60561(12) 0.0533(4) Uani 1 d . . .
N3 N 0.51013(10) 0.06358(14) 0.67975(11) 0.0487(3) Uani 1 d . . .
N4 N 0.75247(9) 0.01060(13) 0.44630(11) 0.0445(3) Uani 1 d . . .
O1 O 0.75925(10) -0.14765(13) 0.58726(11) 0.0624(4) Uani 1 d . . .
O2 O 0.65417(8) 0.11087(12) 0.29819(8) 0.0474(3) Uani 1 d . . .
H2A H 0.6148 0.0541 0.2975 0.071 Uiso 1 calc . . GR


_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 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 N1 1.458(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(2) . ?
C2 N1 1.341(2) . ?
C3 C4 1.429(2) . ?
C3 C7 1.399(2) . ?
C4 N2 1.344(2) . ?
C4 N3 1.369(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.416(2) . ?
C5 N3 1.319(2) . ?
C6 C7 1.368(2) . ?
C6 C9 1.484(2) . ?
C7 C8 1.523(2) . ?
C8 C16 1.522(2) . ?
C8 N4 1.479(2) . ?
C8 O2 1.4070(17) . ?
C9 N4 1.375(2) . ?
C9 O1 1.216(2) . ?
C10 C11 1.376(2) . ?
C10 C15 1.372(2) . ?
C10 N4 1.439(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.361(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(2) . ?
C16 C21 1.375(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9300 . ?
N1 N2 1.361(2) . ?
O2 H2A 0.8200 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
C3 C2 H2 127.0 . . ?
N1 C2 H2 127.0 . . ?
N1 C2 C3 105.96(14) . . ?
C2 C3 C4 104.70(14) . . ?
C2 C3 C7 138.51(14) . . ?
C7 C3 C4 116.61(14) . . ?
N2 C4 C3 111.46(14) . . ?
N2 C4 N3 123.17(14) . . ?
N3 C4 C3 125.27(15) . . ?
C6 C5 H5 118.4 . . ?
N3 C5 H5 118.4 . . ?
N3 C5 C6 123.21(15) . . ?
C5 C6 C9 129.93(14) . . ?
C7 C6 C5 121.28(15) . . ?
C7 C6 C9 108.69(13) . . ?
C3 C7 C8 130.86(13) . . ?
C6 C7 C3 118.09(13) . . ?
C6 C7 C8 111.00(13) . . ?
C16 C8 C7 111.71(12) . . ?
N4 C8 C7 100.38(11) . . ?
N4 C8 C16 111.71(12) . . ?
O2 C8 C7 111.52(12) . . ?
O2 C8 C16 109.27(12) . . ?
O2 C8 N4 112.06(12) . . ?
N4 C9 C6 106.20(13) . . ?
O1 C9 C6 127.59(15) . . ?
O1 C9 N4 126.21(16) . . ?
C11 C10 N4 121.16(15) . . ?
C15 C10 C11 119.60(16) . . ?
C15 C10 N4 119.24(14) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.10(18) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.40(18) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.43(18) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.86(18) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 119.56(17) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C8 119.63(14) . . ?
C21 C16 C8 121.91(14) . . ?
C21 C16 C17 118.47(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.96(17) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.13(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.31(18) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.71(17) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 120.41(16) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C2 N1 C1 126.28(16) . . ?
C2 N1 N2 114.62(14) . . ?
N2 N1 C1 119.01(15) . . ?
C4 N2 N1 103.25(13) . . ?
C5 N3 C4 115.54(13) . . ?
C9 N4 C8 113.71(13) . . ?
C9 N4 C10 123.38(13) . . ?
C10 N4 C8 122.78(12) . . ?
C8 O2 H2A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 O1 0.93 2.36 3.103(2) 136.6 4
O2 H2A N3 0.82 2.22 3.0248(18) 165.7 3_656

_olex2_submission_special_instructions 'No special instructions were received'
