# Supplementary Information (SI) for RSC Advances.
# 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. 
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data_exter108_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2490627'
loop_
_audit_author_name
_audit_author_address
'Hari Prasad Kokatla'
;National Institute of Technology Warangal
India
;
_audit_update_record             
;
2025-09-23 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2023-09-28
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N3 O'
_chemical_formula_sum            'C27 H23 N3 O'
_chemical_formula_weight         405.48
_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'

_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                   11.2233(18)
_cell_length_b                   21.237(3)
_cell_length_c                   9.1008(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.530(6)
_cell_angle_gamma                90
_cell_volume                     2125.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1633 before and 0.0872 after correction.
The Ratio of minimum to maximum transmission is 0.4725.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.111
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            33877
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.623
_diffrn_reflns_theta_min         1.852
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3696
_reflns_number_total             4913
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.062
_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)+(0.0765P)²+0.5101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1624
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C13(H13), C4(H4), C18(H18), C5(H5), C12(H12), C7(H7), C10(H10),
 C23(H23), C11(H11), C6(H6), C20(H20), C22(H22), C21(H21)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.17783(12) 0.61999(7) 0.06383(16) 0.0642(4) Uani 1 1 d . . . . .
N1 N 0.48341(13) 0.45178(6) 0.15045(15) 0.0448(3) Uani 1 1 d . . . . .
N2 N 0.34753(14) 0.67809(6) 0.15482(17) 0.0500(4) Uani 1 1 d . . . . .
N3 N 0.15768(15) 0.53049(9) 0.57866(18) 0.0615(5) Uani 1 1 d . . . . .
C14 C 0.43459(14) 0.62338(7) 0.36396(18) 0.0385(3) Uani 1 1 d . . . . .
C2 C 0.36331(14) 0.52493(7) 0.22489(16) 0.0371(3) Uani 1 1 d . . . . .
C3 C 0.28694(15) 0.47638(7) 0.14573(17) 0.0404(4) Uani 1 1 d . . . . .
C15 C 0.32393(14) 0.58556(7) 0.28998(17) 0.0378(3) Uani 1 1 d . . . . .
C1 C 0.48023(15) 0.50784(7) 0.22344(17) 0.0401(4) Uani 1 1 d . . . . .
H1 H 0.548507 0.531148 0.266281 0.048 Uiso 1 1 calc R . . . .
C16 C 0.26942(16) 0.62872(8) 0.15529(19) 0.0449(4) Uani 1 1 d . . . . .
C17 C 0.23639(15) 0.57425(8) 0.39378(18) 0.0418(4) Uani 1 1 d . . . . .
C9 C 0.44617(16) 0.67552(7) 0.2760(2) 0.0441(4) Uani 1 1 d . . . . .
C8 C 0.36602(16) 0.43159(8) 0.10196(18) 0.0439(4) Uani 1 1 d . . . . .
C13 C 0.52036(16) 0.61203(8) 0.49108(19) 0.0467(4) Uani 1 1 d . . . . .
H13 H 0.512182 0.577774 0.551952 0.056 Uiso 1 1 calc R . . . .
C24 C 0.14997(15) 0.61746(9) 0.4347(2) 0.0488(4) Uani 1 1 d . . . . .
C4 C 0.16228(16) 0.46596(9) 0.1074(2) 0.0501(4) Uani 1 1 d . . . . .
H4 H 0.108233 0.494888 0.134381 0.060 Uiso 1 1 calc R . . . .
C18 C 0.23638(17) 0.52232(9) 0.48284(19) 0.0508(4) Uani 1 1 d . . . . .
H18 H 0.283237 0.486474 0.478882 0.061 Uiso 1 1 calc R . . . .
C19 C 0.10502(17) 0.58872(11) 0.5521(2) 0.0573(5) Uani 1 1 d . . . . .
C5 C 0.11976(19) 0.41238(10) 0.0293(2) 0.0619(5) Uani 1 1 d . . . . .
H5 H 0.036469 0.405011 0.004498 0.074 Uiso 1 1 calc R . . . .
C12 C 0.61958(18) 0.65210(9) 0.5282(2) 0.0586(5) Uani 1 1 d . . . . .
H12 H 0.678380 0.644639 0.614074 0.070 Uiso 1 1 calc R . . . .
C7 C 0.3231(2) 0.37757(9) 0.0212(2) 0.0580(5) Uani 1 1 d . . . . .
H7 H 0.376076 0.348612 -0.007938 0.070 Uiso 1 1 calc R . . . .
C10 C 0.54428(19) 0.71590(8) 0.3112(3) 0.0594(5) Uani 1 1 d . . . . .
H10 H 0.551716 0.750661 0.251532 0.071 Uiso 1 1 calc R . . . .
C23 C 0.10349(19) 0.67599(10) 0.3827(3) 0.0631(5) Uani 1 1 d . . . . .
H23 H 0.129018 0.695388 0.302729 0.076 Uiso 1 1 calc R . . . .
C11 C 0.63089(19) 0.70284(9) 0.4381(3) 0.0648(6) Uani 1 1 d . . . . .
H11 H 0.698436 0.728939 0.463121 0.078 Uiso 1 1 calc R . . . .
C26 C 0.59197(18) 0.41669(10) 0.1412(2) 0.0600(5) Uani 1 1 d . . . . .
H26A H 0.653508 0.445073 0.121569 0.090 Uiso 1 1 calc GR . . . .
H26B H 0.573625 0.386434 0.061482 0.090 Uiso 1 1 calc GR . . . .
H26C H 0.620886 0.395240 0.234342 0.090 Uiso 1 1 calc GR . . . .
C6 C 0.1997(2) 0.36899(10) -0.0133(2) 0.0664(6) Uani 1 1 d . . . . .
H6 H 0.168405 0.333272 -0.066463 0.080 Uiso 1 1 calc R . . . .
C27 C 0.3262(2) 0.72824(11) 0.0442(3) 0.0788(7) Uani 1 1 d . . . . .
H27A H 0.262007 0.716130 -0.037317 0.118 Uiso 1 1 calc GR . . . .
H27B H 0.399150 0.735779 0.006903 0.118 Uiso 1 1 calc GR . . . .
H27C H 0.303400 0.765951 0.089740 0.118 Uiso 1 1 calc GR . . . .
C20 C 0.0200(2) 0.61870(16) 0.6225(3) 0.0847(8) Uani 1 1 d . . . . .
H20 H -0.007361 0.599972 0.702036 0.102 Uiso 1 1 calc R . . . .
C25 C 0.1355(2) 0.48542(14) 0.6902(3) 0.0853(8) Uani 1 1 d . . . . .
H25A H 0.051342 0.473380 0.668844 0.128 Uiso 1 1 calc GR . . . .
H25B H 0.155166 0.504252 0.787946 0.128 Uiso 1 1 calc GR . . . .
H25C H 0.185273 0.448851 0.687498 0.128 Uiso 1 1 calc GR . . . .
C22 C 0.0190(2) 0.70470(13) 0.4517(3) 0.0859(8) Uani 1 1 d . . . . .
H22 H -0.011609 0.743943 0.417935 0.103 Uiso 1 1 calc R . . . .
C21 C -0.0210(2) 0.67671(16) 0.5691(4) 0.0957(9) Uani 1 1 d . . . . .
H21 H -0.077334 0.697726 0.613527 0.115 Uiso 1 1 calc R . . . .


_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
O1 C16 1.201(2) . ?
N1 C1 1.367(2) . ?
N1 C8 1.372(2) . ?
N1 C26 1.445(2) . ?
N2 C16 1.367(2) . ?
N2 C9 1.399(2) . ?
N2 C27 1.452(2) . ?
N3 C18 1.371(2) . ?
N3 C19 1.371(3) . ?
N3 C25 1.452(3) . ?
C14 C15 1.519(2) . ?
C14 C9 1.388(2) . ?
C14 C13 1.370(2) . ?
C2 C3 1.439(2) . ?
C2 C15 1.520(2) . ?
C2 C1 1.364(2) . ?
C3 C8 1.412(2) . ?
C3 C4 1.390(2) . ?
C15 C16 1.555(2) . ?
C15 C17 1.512(2) . ?
C17 C24 1.437(2) . ?
C17 C18 1.369(2) . ?
C9 C10 1.382(3) . ?
C8 C7 1.395(2) . ?
C13 C12 1.389(3) . ?
C24 C19 1.409(3) . ?
C24 C23 1.394(3) . ?
C4 C5 1.376(3) . ?
C19 C20 1.404(3) . ?
C5 C6 1.394(3) . ?
C12 C11 1.376(3) . ?
C7 C6 1.370(3) . ?
C10 C11 1.381(3) . ?
C23 C22 1.379(3) . ?
C20 C21 1.370(4) . ?
C22 C21 1.374(4) . ?

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 C8 108.17(14) . . ?
C1 N1 C26 125.57(15) . . ?
C8 N1 C26 125.92(15) . . ?
C16 N2 C9 112.00(13) . . ?
C16 N2 C27 123.21(17) . . ?
C9 N2 C27 124.75(17) . . ?
C18 N3 C19 108.18(16) . . ?
C18 N3 C25 125.7(2) . . ?
C19 N3 C25 126.1(2) . . ?
C9 C14 C15 109.20(14) . . ?
C13 C14 C15 130.95(14) . . ?
C13 C14 C9 119.76(15) . . ?
C3 C2 C15 127.73(14) . . ?
C1 C2 C3 106.41(14) . . ?
C1 C2 C15 125.77(14) . . ?
C8 C3 C2 106.20(14) . . ?
C4 C3 C2 135.12(16) . . ?
C4 C3 C8 118.68(15) . . ?
C14 C15 C2 110.19(12) . . ?
C14 C15 C16 101.30(13) . . ?
C2 C15 C16 106.95(12) . . ?
C17 C15 C14 112.52(13) . . ?
C17 C15 C2 112.63(13) . . ?
C17 C15 C16 112.57(13) . . ?
C2 C1 N1 110.79(14) . . ?
O1 C16 N2 125.22(16) . . ?
O1 C16 C15 127.09(16) . . ?
N2 C16 C15 107.64(14) . . ?
C24 C17 C15 128.08(15) . . ?
C18 C17 C15 125.09(15) . . ?
C18 C17 C24 106.33(15) . . ?
C14 C9 N2 109.59(15) . . ?
C10 C9 N2 128.83(16) . . ?
C10 C9 C14 121.57(17) . . ?
N1 C8 C3 108.43(14) . . ?
N1 C8 C7 129.39(17) . . ?
C7 C8 C3 122.18(17) . . ?
C14 C13 C12 119.45(17) . . ?
C19 C24 C17 106.41(17) . . ?
C23 C24 C17 135.05(18) . . ?
C23 C24 C19 118.52(18) . . ?
C5 C4 C3 119.27(19) . . ?
C17 C18 N3 110.55(18) . . ?
N3 C19 C24 108.50(17) . . ?
N3 C19 C20 129.6(2) . . ?
C20 C19 C24 121.9(2) . . ?
C4 C5 C6 120.96(19) . . ?
C11 C12 C13 120.00(19) . . ?
C6 C7 C8 117.18(19) . . ?
C11 C10 C9 117.67(18) . . ?
C22 C23 C24 119.0(2) . . ?
C12 C11 C10 121.52(18) . . ?
C7 C6 C5 121.72(18) . . ?
C21 C20 C19 117.2(2) . . ?
C21 C22 C23 121.6(3) . . ?
C20 C21 C22 121.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
