# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_KB613_0m
_database_code_depnum_ccdc_archive 'CCDC 2267726'
loop_
_audit_author_name
_audit_author_address
Darshini
;University of Mysore
India
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O'
_chemical_formula_sum            'C23 H21 N3 O'
_chemical_formula_weight         355.43

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 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   10.7713(16)
_cell_length_b                   13.2410(18)
_cell_length_c                   13.3621(18)
_cell_angle_alpha                90
_cell_angle_beta                 108.828(5)
_cell_angle_gamma                90
_cell_volume                     1803.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.16

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28295
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4441
_reflns_number_gt                3437
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.5253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4441
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.65073(13) 0.40450(9) 0.42576(10) 0.0445(3) Uani 1 1 d . . . . .
O1 O 0.26448(10) 0.77922(8) 0.21555(8) 0.0471(3) Uani 1 1 d . . . . .
N2 N 0.69973(11) 0.48784(9) 0.48801(9) 0.0372(3) Uani 1 1 d . . . . .
N3 N 0.63657(11) 0.66557(9) 0.49266(9) 0.0369(3) Uani 1 1 d . . . . .
H3 H 0.701705 0.681439 0.547354 0.044 Uiso 1 1 calc R U . . .
C2 C 0.62577(13) 0.57037(10) 0.44733(10) 0.0334(3) Uani 1 1 d . . . . .
C3 C 0.54911(14) 0.43924(11) 0.34841(11) 0.0417(3) Uani 1 1 d . . . . .
H3A H 0.496385 0.399028 0.294223 0.050 Uiso 1 1 calc R U . . .
C4 C 0.44012(12) 0.61988(10) 0.28582(10) 0.0318(3) Uani 1 1 d . . . . .
H4 H 0.350200 0.593732 0.263039 0.038 Uiso 1 1 calc R U . . .
C5 C 0.44541(12) 0.71585(10) 0.35006(10) 0.0309(3) Uani 1 1 d . . . . .
C6 C 0.53845(12) 0.73318(10) 0.44614(10) 0.0320(3) Uani 1 1 d . . . . .
C7 C 0.34750(13) 0.79207(10) 0.30325(10) 0.0344(3) Uani 1 1 d . . . . .
C8 C 0.34651(16) 0.88819(11) 0.36352(13) 0.0470(4) Uani 1 1 d . . . . .
H8A H 0.256775 0.911380 0.347534 0.056 Uiso 1 1 calc R U . . .
H8B H 0.394953 0.939885 0.340350 0.056 Uiso 1 1 calc R U . . .
C9 C 0.40656(15) 0.87410(12) 0.48197(12) 0.0446(4) Uani 1 1 d . . . . .
H9A H 0.412408 0.938843 0.517161 0.054 Uiso 1 1 calc R U . . .
H9B H 0.351197 0.830126 0.507413 0.054 Uiso 1 1 calc R U . . .
C10 C 0.54153(14) 0.82850(11) 0.50767(11) 0.0414(3) Uani 1 1 d . . . . .
H10A H 0.599854 0.876796 0.491237 0.050 Uiso 1 1 calc R U . . .
H10B H 0.575682 0.813814 0.582731 0.050 Uiso 1 1 calc R U . . .
C11 C 0.48083(13) 0.63999(10) 0.18798(10) 0.0336(3) Uani 1 1 d . . . . .
C12 C 0.40096(14) 0.61209(11) 0.08841(11) 0.0401(3) Uani 1 1 d . . . . .
H12 H 0.321767 0.580116 0.081566 0.048 Uiso 1 1 calc R U . . .
C13 C 0.43496(17) 0.63018(13) -0.00211(12) 0.0490(4) Uani 1 1 d . . . . .
C14 C 0.55345(19) 0.67779(14) 0.01047(14) 0.0566(4) Uani 1 1 d . . . . .
H14 H 0.578192 0.691295 -0.048736 0.068 Uiso 1 1 calc R U . . .
C15 C 0.63560(18) 0.70560(14) 0.10918(15) 0.0574(4) Uani 1 1 d . . . . .
H15 H 0.715096 0.737101 0.116076 0.069 Uiso 1 1 calc R U . . .
C16 C 0.59962(15) 0.68657(12) 0.19797(13) 0.0465(4) Uani 1 1 d . . . . .
H16 H 0.655229 0.705077 0.264470 0.056 Uiso 1 1 calc R U . . .
C17 C 0.3445(2) 0.5988(2) -0.10931(14) 0.0771(6) Uani 1 1 d . . . . .
H17A H 0.351976 0.645910 -0.161694 0.116 Uiso 1 1 calc R U . . .
H17B H 0.255710 0.598016 -0.108524 0.116 Uiso 1 1 calc R U . . .
H17C H 0.368252 0.532550 -0.125968 0.116 Uiso 1 1 calc R U . . .
C18 C 0.82254(13) 0.47962(11) 0.56979(11) 0.0368(3) Uani 1 1 d . . . . .
C19 C 0.91585(15) 0.55486(12) 0.58653(14) 0.0505(4) Uani 1 1 d . . . . .
H19 H 0.897133 0.614424 0.547652 0.061 Uiso 1 1 calc R U . . .
C20 C 1.03759(18) 0.54056(15) 0.66189(17) 0.0648(5) Uani 1 1 d . . . . .
H20 H 1.100956 0.590865 0.673724 0.078 Uiso 1 1 calc R U . . .
C21 C 1.06562(18) 0.45198(15) 0.71968(15) 0.0644(5) Uani 1 1 d . . . . .
H21 H 1.147863 0.442430 0.769660 0.077 Uiso 1 1 calc R U . . .
C22 C 0.97182(18) 0.37841(13) 0.70304(14) 0.0571(4) Uani 1 1 d . . . . .
H22 H 0.990429 0.319072 0.742311 0.069 Uiso 1 1 calc R U . . .
C23 C 0.85002(16) 0.39159(12) 0.62852(13) 0.0462(4) Uani 1 1 d . . . . .
H23 H 0.786557 0.341470 0.617779 0.055 Uiso 1 1 calc R U . . .
C1 C 0.52923(13) 0.54322(10) 0.35672(10) 0.0340(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
N1 C3 1.3221(19) . ?
N1 N2 1.3801(16) . ?
O1 C7 1.2351(16) . ?
N2 C2 1.3583(17) . ?
N2 C18 1.4223(17) . ?
N3 C6 1.3714(16) . ?
N3 C2 1.3870(17) . ?
N3 H3 0.8600 . ?
C2 C1 1.3652(17) . ?
C3 C1 1.403(2) . ?
C3 H3A 0.9300 . ?
C4 C1 1.5040(18) . ?
C4 C5 1.5243(18) . ?
C4 C11 1.5305(18) . ?
C4 H4 0.9800 . ?
C5 C6 1.3693(17) . ?
C5 C7 1.4478(18) . ?
C6 C10 1.5008(19) . ?
C7 C8 1.508(2) . ?
C8 C9 1.516(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.508(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.3814(19) . ?
C11 C16 1.387(2) . ?
C12 C13 1.393(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(3) . ?
C13 C17 1.507(2) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.381(2) . ?
C18 C23 1.383(2) . ?
C19 C20 1.385(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(2) . ?
C22 H22 0.9300 . ?
C23 H23 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
C3 N1 N2 104.60(11) . . ?
C2 N2 N1 109.96(11) . . ?
C2 N2 C18 130.47(12) . . ?
N1 N2 C18 118.80(11) . . ?
C6 N3 C2 116.85(11) . . ?
C6 N3 H3 121.6 . . ?
C2 N3 H3 121.6 . . ?
N2 C2 C1 108.87(12) . . ?
N2 C2 N3 126.92(11) . . ?
C1 C2 N3 124.00(12) . . ?
N1 C3 C1 112.86(12) . . ?
N1 C3 H3A 123.6 . . ?
C1 C3 H3A 123.6 . . ?
C1 C4 C5 107.92(10) . . ?
C1 C4 C11 110.79(11) . . ?
C5 C4 C11 111.53(11) . . ?
C1 C4 H4 108.8 . . ?
C5 C4 H4 108.8 . . ?
C11 C4 H4 108.8 . . ?
C6 C5 C7 119.93(12) . . ?
C6 C5 C4 123.42(11) . . ?
C7 C5 C4 116.63(11) . . ?
C5 C6 N3 122.64(12) . . ?
C5 C6 C10 122.32(12) . . ?
N3 C6 C10 115.04(11) . . ?
O1 C7 C5 121.15(13) . . ?
O1 C7 C8 119.68(12) . . ?
C5 C7 C8 119.16(11) . . ?
C7 C8 C9 112.31(12) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 110.01(13) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C6 C10 C9 111.27(11) . . ?
C6 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C6 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C16 118.68(13) . . ?
C12 C11 C4 121.01(12) . . ?
C16 C11 C4 120.32(12) . . ?
C11 C12 C13 122.26(14) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 117.60(14) . . ?
C14 C13 C17 121.92(16) . . ?
C12 C13 C17 120.48(17) . . ?
C15 C14 C13 121.27(15) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.99(16) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.19(15) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 120.32(14) . . ?
C19 C18 N2 121.13(13) . . ?
C23 C18 N2 118.44(13) . . ?
C18 C19 C20 119.21(15) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 120.46(17) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.74(16) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.51(16) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 119.75(15) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
C2 C1 C3 103.68(12) . . ?
C2 C1 C4 121.97(12) . . ?
C3 C1 C4 134.03(12) . . ?

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
C3 N1 N2 C2 0.63(16) . . . . ?
C3 N1 N2 C18 -170.34(13) . . . . ?
N1 N2 C2 C1 -1.40(16) . . . . ?
C18 N2 C2 C1 168.19(13) . . . . ?
N1 N2 C2 N3 173.52(13) . . . . ?
C18 N2 C2 N3 -16.9(2) . . . . ?
C6 N3 C2 N2 -169.79(13) . . . . ?
C6 N3 C2 C1 4.4(2) . . . . ?
N2 N1 C3 C1 0.36(17) . . . . ?
C1 C4 C5 C6 13.53(17) . . . . ?
C11 C4 C5 C6 -108.38(14) . . . . ?
C1 C4 C5 C7 -168.15(11) . . . . ?
C11 C4 C5 C7 69.94(14) . . . . ?
C7 C5 C6 N3 -177.52(12) . . . . ?
C4 C5 C6 N3 0.8(2) . . . . ?
C7 C5 C6 C10 1.6(2) . . . . ?
C4 C5 C6 C10 179.89(13) . . . . ?
C2 N3 C6 C5 -10.7(2) . . . . ?
C2 N3 C6 C10 170.08(12) . . . . ?
C6 C5 C7 O1 178.27(13) . . . . ?
C4 C5 C7 O1 -0.11(19) . . . . ?
C6 C5 C7 C8 -2.4(2) . . . . ?
C4 C5 C7 C8 179.24(12) . . . . ?
O1 C7 C8 C9 153.62(14) . . . . ?
C5 C7 C8 C9 -25.7(2) . . . . ?
C7 C8 C9 C10 53.37(18) . . . . ?
C5 C6 C10 C9 27.19(19) . . . . ?
N3 C6 C10 C9 -153.62(13) . . . . ?
C8 C9 C10 C6 -53.63(17) . . . . ?
C1 C4 C11 C12 113.21(14) . . . . ?
C5 C4 C11 C12 -126.55(13) . . . . ?
C1 C4 C11 C16 -66.57(16) . . . . ?
C5 C4 C11 C16 53.67(17) . . . . ?
C16 C11 C12 C13 -0.8(2) . . . . ?
C4 C11 C12 C13 179.45(13) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C11 C12 C13 C17 -179.74(16) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C17 C13 C14 C15 -179.65(18) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
C12 C11 C16 C15 0.9(2) . . . . ?
C4 C11 C16 C15 -179.35(14) . . . . ?
C2 N2 C18 C19 -32.5(2) . . . . ?
N1 N2 C18 C19 136.27(15) . . . . ?
C2 N2 C18 C23 151.29(15) . . . . ?
N1 N2 C18 C23 -39.89(19) . . . . ?
C23 C18 C19 C20 0.7(3) . . . . ?
N2 C18 C19 C20 -175.34(16) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?
C19 C18 C23 C22 -0.9(2) . . . . ?
N2 C18 C23 C22 175.26(15) . . . . ?
N2 C2 C1 C3 1.51(15) . . . . ?
N3 C2 C1 C3 -173.59(13) . . . . ?
N2 C2 C1 C4 -172.82(12) . . . . ?
N3 C2 C1 C4 12.1(2) . . . . ?
N1 C3 C1 C2 -1.17(17) . . . . ?
N1 C3 C1 C4 172.13(14) . . . . ?
C5 C4 C1 C2 -19.43(17) . . . . ?
C11 C4 C1 C2 102.94(14) . . . . ?
C5 C4 C1 C3 168.24(15) . . . . ?
C11 C4 C1 C3 -69.4(2) . . . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.038

