# 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_AKB_PS_770
_database_code_depnum_ccdc_archive 'CCDC 2451382'
loop_
_audit_author_name
_audit_author_address
'Dr. Avik Kumar Bagdi'
;University of Kalyani
India
;
_audit_update_record             
;
2025-05-15 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_iupac          ?
_chemical_formula_moiety         'C20 H15 N3 O'
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35
_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'
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'
H H 0.0000 0.0000 '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/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                   12.9831(9)
_cell_length_b                   7.4371(5)
_cell_length_c                   16.6855(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.025(2)
_cell_angle_gamma                90
_cell_volume                     1581.36(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    299.(2)
_cell_measurement_theta_max      24.2592
_cell_measurement_theta_min      2.4872
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
;
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            58971
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.49
_diffrn_ambient_temperature      299.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           ?
_diffrn_source_power             ?
_diffrn_source_type              ?
_diffrn_source_voltage           ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1911
_reflns_number_total             2786
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.221
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    ?
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.135
_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)+(0.0327P)²+1.0629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1426
_refine_special_details          
;
;
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15), C19(H19)
1.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4214(2) 0.7476(4) -0.06080(13) 0.0982(9) Uani d . . . 1 . .
N N1 0.14357(19) 0.6349(3) 0.04202(14) 0.0635(7) Uani d . . . 1 . .
N N2 0.27054(16) 0.6879(3) 0.16390(12) 0.0484(6) Uani d . . . 1 . .
N N3 0.37392(17) 0.7386(3) 0.18783(13) 0.0552(6) Uani d . . . 1 . .
C C1 0.3164(2) 0.6566(4) 0.56620(16) 0.0544(7) Uani d . . . 1 . .
C C2 0.2897(2) 0.7937(5) 0.61453(19) 0.0727(9) Uani d . . . 1 . .
H H2 0.252510 0.892453 0.589937 0.087000 Uiso calc U . R 1 . .
C C3 0.3172(3) 0.7863(6) 0.6987(2) 0.0868(12) Uani d . . . 1 . .
H H3 0.298267 0.879447 0.730125 0.104000 Uiso calc U . R 1 . .
C C4 0.3720(3) 0.6432(7) 0.7357(2) 0.0871(12) Uani d . . . 1 . .
H H4 0.390690 0.639390 0.792370 0.105000 Uiso calc U . R 1 . .
C C5 0.3999(2) 0.5041(6) 0.68975(19) 0.0783(11) Uani d . . . 1 . .
H H5 0.436972 0.405993 0.715135 0.094000 Uiso calc U . R 1 . .
C C6 0.3723(2) 0.5113(5) 0.60525(17) 0.0636(8) Uani d . . . 1 . .
H H6 0.391501 0.417643 0.574213 0.076000 Uiso calc U . R 1 . .
C C7 0.2880(2) 0.6626(4) 0.47599(16) 0.0495(7) Uani d . . . 1 . .
C C8 0.3574(2) 0.6034(4) 0.42779(16) 0.0552(7) Uani d . . . 1 . .
H H8 0.422887 0.560776 0.453057 0.066000 Uiso calc U . R 1 . .
C C9 0.3324(2) 0.6059(4) 0.34403(16) 0.0534(7) Uani d . . . 1 . .
H H9 0.381247 0.566815 0.313754 0.064000 Uiso calc U . R 1 . .
C C10 0.2349(2) 0.6662(4) 0.30421(15) 0.0478(7) Uani d . . . 1 . .
C C11 0.1650(2) 0.7268(4) 0.35171(16) 0.0542(7) Uani d . . . 1 . .
H H11 0.099324 0.768619 0.326358 0.065000 Uiso calc U . R 1 . .
C C12 0.1914(2) 0.7262(4) 0.43590(16) 0.0551(7) Uani d . . . 1 . .
H H12 0.143518 0.769148 0.466250 0.066000 Uiso calc U . R 1 . .
C C13 0.2014(2) 0.6573(4) 0.21476(16) 0.0494(7) Uani d . . . 1 . .
C C14 0.1020(2) 0.6146(4) 0.17626(17) 0.0597(8) Uani d . . . 1 . .
H H14 0.050789 0.591173 0.206904 0.072000 Uiso calc U . R 1 . .
C C15 0.0767(2) 0.6059(4) 0.09116(18) 0.0660(8) Uani d . . . 1 . .
H H15 0.007879 0.577651 0.067394 0.079000 Uiso calc U . R 1 . .
C C16 0.2416(2) 0.6780(4) 0.07950(16) 0.0529(7) Uani d . . . 1 . .
C C17 0.3316(2) 0.7202(4) 0.04921(16) 0.0554(7) Uani d . . . 1 . .
C C18 0.4090(2) 0.7564(4) 0.11846(17) 0.0565(7) Uani d . . . 1 . .
C C19 0.3407(3) 0.7246(4) -0.03560(19) 0.0708(9) Uani d . . . 1 . .
H H19 0.279473 0.708550 -0.074221 0.085000 Uiso calc U . R 1 . .
C C20 0.5197(2) 0.8127(5) 0.1215(2) 0.0835(11) Uani d . . . 1 . .
H H20A 0.521141 0.915881 0.087169 0.125000 Uiso calc U . R 1 . .
H H20B 0.557884 0.715989 0.102722 0.125000 Uiso calc U . R 1 . .
H H20C 0.551466 0.842696 0.176693 0.125000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C19 . 1.213(4) ?
N1 C15 . 1.321(4) ?
N1 C16 . 1.345(3) ?
N2 N3 . 1.378(3) ?
N2 C13 . 1.367(3) ?
N2 C16 . 1.388(3) ?
N3 C18 . 1.329(3) ?
C1 C2 . 1.385(4) ?
C1 C6 . 1.392(4) ?
C1 C7 . 1.480(4) ?
C2 H2 . 0.930000 ?
C2 C3 . 1.383(4) ?
C3 H3 . 0.930000 ?
C3 C4 . 1.361(5) ?
C4 H4 . 0.930000 ?
C4 C5 . 1.378(5) ?
C5 H5 . 0.930000 ?
C5 C6 . 1.388(4) ?
C6 H6 . 0.930000 ?
C7 C8 . 1.388(3) ?
C7 C12 . 1.387(4) ?
C8 H8 . 0.930000 ?
C8 C9 . 1.373(4) ?
C9 H9 . 0.930000 ?
C9 C10 . 1.387(3) ?
C10 C11 . 1.389(3) ?
C10 C13 . 1.474(4) ?
C11 H11 . 0.930000 ?
C11 C12 . 1.381(4) ?
C12 H12 . 0.930000 ?
C13 C14 . 1.364(4) ?
C14 H14 . 0.930000 ?
C14 C15 . 1.396(4) ?
C15 H15 . 0.930000 ?
C16 C17 . 1.395(4) ?
C17 C18 . 1.404(4) ?
C17 C19 . 1.443(4) ?
C18 C20 . 1.489(4) ?
C19 H19 . 0.930000 ?
C20 H20A . 0.960000 ?
C20 H20B . 0.960000 ?
C20 H20C . 0.960000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 N1 C16 . . 115.2(2) ?
N3 N2 C16 . . 111.6(2) ?
C13 N2 N3 . . 125.8(2) ?
C13 N2 C16 . . 122.5(2) ?
C18 N3 N2 . . 104.6(2) ?
C2 C1 C6 . . 117.7(3) ?
C2 C1 C7 . . 121.9(3) ?
C6 C1 C7 . . 120.3(3) ?
C1 C2 H2 . . 119.400000 ?
C3 C2 C1 . . 121.2(3) ?
C3 C2 H2 . . 119.400000 ?
C2 C3 H3 . . 119.900000 ?
C4 C3 C2 . . 120.2(4) ?
C4 C3 H3 . . 119.900000 ?
C3 C4 H4 . . 119.800000 ?
C3 C4 C5 . . 120.3(3) ?
C5 C4 H4 . . 119.800000 ?
C4 C5 H5 . . 120.300000 ?
C4 C5 C6 . . 119.5(3) ?
C6 C5 H5 . . 120.300000 ?
C1 C6 H6 . . 119.500000 ?
C5 C6 C1 . . 121.1(3) ?
C5 C6 H6 . . 119.500000 ?
C8 C7 C1 . . 121.1(2) ?
C12 C7 C1 . . 121.8(2) ?
C12 C7 C8 . . 117.1(2) ?
C7 C8 H8 . . 118.900000 ?
C9 C8 C7 . . 122.2(3) ?
C9 C8 H8 . . 118.900000 ?
C8 C9 H9 . . 119.700000 ?
C8 C9 C10 . . 120.6(2) ?
C10 C9 H9 . . 119.700000 ?
C9 C10 C11 . . 117.9(2) ?
C9 C10 C13 . . 122.4(2) ?
C11 C10 C13 . . 119.6(2) ?
C10 C11 H11 . . 119.400000 ?
C12 C11 C10 . . 121.2(3) ?
C12 C11 H11 . . 119.400000 ?
C7 C12 H12 . . 119.400000 ?
C11 C12 C7 . . 121.1(2) ?
C11 C12 H12 . . 119.400000 ?
N2 C13 C10 . . 121.3(2) ?
C14 C13 N2 . . 114.9(2) ?
C14 C13 C10 . . 123.8(2) ?
C13 C14 H14 . . 119.800000 ?
C13 C14 C15 . . 120.5(3) ?
C15 C14 H14 . . 119.800000 ?
N1 C15 C14 . . 124.7(3) ?
N1 C15 H15 . . 117.700000 ?
C14 C15 H15 . . 117.700000 ?
N1 C16 N2 . . 122.2(2) ?
N1 C16 C17 . . 132.0(3) ?
N2 C16 C17 . . 105.8(2) ?
C16 C17 C18 . . 105.2(2) ?
C16 C17 C19 . . 126.3(3) ?
C18 C17 C19 . . 128.6(3) ?
N3 C18 C17 . . 112.8(2) ?
N3 C18 C20 . . 119.2(3) ?
C17 C18 C20 . . 128.0(3) ?
O1 C19 C17 . . 125.5(3) ?
O1 C19 H19 . . 117.200000 ?
C17 C19 H19 . . 117.200000 ?
C18 C20 H20A . . 109.500000 ?
C18 C20 H20B . . 109.500000 ?
C18 C20 H20C . . 109.500000 ?
H20A C20 H20B . . 109.500000 ?
H20A C20 H20C . . 109.500000 ?
H20B C20 H20C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C16 C17 C18 . . . . 178.8(3) ?
N1 C16 C17 C19 . . . . -1.1(5) ?
N2 N3 C18 C17 . . . . 0.4(3) ?
N2 N3 C18 C20 . . . . 179.4(3) ?
N2 C13 C14 C15 . . . . -0.4(4) ?
N2 C16 C17 C18 . . . . -1.1(3) ?
N2 C16 C17 C19 . . . . 178.9(3) ?
N3 N2 C13 C10 . . . . -3.7(4) ?
N3 N2 C13 C14 . . . . 177.8(2) ?
N3 N2 C16 N1 . . . . -178.5(2) ?
N3 N2 C16 C17 . . . . 1.4(3) ?
C1 C2 C3 C4 . . . . 0.3(5) ?
C1 C7 C8 C9 . . . . 179.3(3) ?
C1 C7 C12 C11 . . . . -178.4(3) ?
C2 C1 C6 C5 . . . . 0.2(4) ?
C2 C1 C7 C8 . . . . 140.4(3) ?
C2 C1 C7 C12 . . . . -39.9(4) ?
C2 C3 C4 C5 . . . . -0.4(5) ?
C3 C4 C5 C6 . . . . 0.4(5) ?
C4 C5 C6 C1 . . . . -0.3(5) ?
C6 C1 C2 C3 . . . . -0.2(4) ?
C6 C1 C7 C8 . . . . -39.1(4) ?
C6 C1 C7 C12 . . . . 140.6(3) ?
C7 C1 C2 C3 . . . . -179.7(3) ?
C7 C1 C6 C5 . . . . 179.8(3) ?
C7 C8 C9 C10 . . . . -0.9(4) ?
C8 C7 C12 C11 . . . . 1.3(4) ?
C8 C9 C10 C11 . . . . 1.3(4) ?
C8 C9 C10 C13 . . . . -174.8(3) ?
C9 C10 C11 C12 . . . . -0.4(4) ?
C9 C10 C13 N2 . . . . -37.2(4) ?
C9 C10 C13 C14 . . . . 141.2(3) ?
C10 C11 C12 C7 . . . . -0.9(4) ?
C10 C13 C14 C15 . . . . -178.9(3) ?
C11 C10 C13 N2 . . . . 146.8(3) ?
C11 C10 C13 C14 . . . . -34.9(4) ?
C12 C7 C8 C9 . . . . -0.4(4) ?
C13 N2 N3 C18 . . . . -178.6(2) ?
C13 N2 C16 N1 . . . . -1.0(4) ?
C13 N2 C16 C17 . . . . 179.0(2) ?
C13 C10 C11 C12 . . . . 175.8(3) ?
C13 C14 C15 N1 . . . . 0.7(5) ?
C15 N1 C16 N2 . . . . 1.1(4) ?
C15 N1 C16 C17 . . . . -178.8(3) ?
C16 N1 C15 C14 . . . . -1.0(5) ?
C16 N2 N3 C18 . . . . -1.1(3) ?
C16 N2 C13 C10 . . . . 179.1(2) ?
C16 N2 C13 C14 . . . . 0.6(4) ?
C16 C17 C18 N3 . . . . 0.5(3) ?
C16 C17 C18 C20 . . . . -178.4(3) ?
C16 C17 C19 O1 . . . . -173.8(3) ?
C18 C17 C19 O1 . . . . 6.3(6) ?
C19 C17 C18 N3 . . . . -179.6(3) ?
C19 C17 C18 C20 . . . . 1.5(5) ?

