# 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_KB1191_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2418004'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-01-19 deposited with the CCDC.	2025-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N2 O'
_chemical_formula_sum            'C20 H18 N2 O'
_chemical_formula_weight         302.36

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                   12.363(3)
_cell_length_b                   9.134(2)
_cell_length_c                   14.586(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.078(10)
_cell_angle_gamma                90
_cell_volume                     1646.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4487
_cell_measurement_theta_min      3.986
_cell_measurement_theta_max      28.152

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.076
_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  0.5694
_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            10590
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.296
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2838
_reflns_number_gt                1710
_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_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.1880P] 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         2838
_refine_ls_number_parameters     230
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_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
C1 C 0.3602(2) 0.5417(3) 0.30963(19) 0.0957(9) Uani 1 1 d D . . . .
H1 H 0.358266 0.616566 0.266416 0.115 Uiso 1 1 calc R U . A 1
C4 C 0.3533(2) 0.3111(3) 0.44182(18) 0.0894(8) Uani 1 1 d D . . . .
H4 H 0.354911 0.237163 0.485648 0.107 Uiso 1 1 calc R U . B 1
C5 C 0.44906(18) 0.3711(3) 0.41248(16) 0.0652(6) Uani 1 1 d . . . . .
C6 C 0.45426(19) 0.4837(3) 0.34778(16) 0.0656(6) Uani 1 1 d . . . . .
C7 C 0.61775(16) 0.4272(2) 0.37783(13) 0.0503(5) Uani 1 1 d . . . . .
C8 C 0.73090(16) 0.37984(19) 0.38700(12) 0.0473(5) Uani 1 1 d . . . . .
C9 C 0.73467(17) 0.2648(2) 0.44578(12) 0.0525(5) Uani 1 1 d . . . . .
C10 C 0.62134(19) 0.2309(2) 0.47431(13) 0.0587(6) Uani 1 1 d . . . . .
C11 C 0.82885(19) 0.1703(2) 0.47933(14) 0.0670(7) Uani 1 1 d . . . . .
C12 C 0.9374(2) 0.2476(4) 0.4694(2) 0.1128(10) Uani 1 1 d . . . . .
H12A H 0.992626 0.193349 0.501669 0.169 Uiso 1 1 calc R U . . .
H12B H 0.932941 0.344473 0.494629 0.169 Uiso 1 1 calc R U . . .
H12C H 0.954887 0.253713 0.405678 0.169 Uiso 1 1 calc R U . . .
C13 C 0.8255(3) 0.0272(3) 0.42410(19) 0.1067(10) Uani 1 1 d . . . . .
H13A H 0.840002 0.047639 0.360967 0.160 Uiso 1 1 calc R U . . .
H13B H 0.755130 -0.016516 0.428638 0.160 Uiso 1 1 calc R U . . .
H13C H 0.879133 -0.039146 0.448181 0.160 Uiso 1 1 calc R U . . .
C14 C 0.8180(2) 0.1347(3) 0.58171(16) 0.1023(10) Uani 1 1 d . . . . .
H14A H 0.751658 0.082479 0.591019 0.153 Uiso 1 1 calc R U . . .
H14B H 0.817459 0.223968 0.616388 0.153 Uiso 1 1 calc R U . . .
H14C H 0.877964 0.075223 0.601670 0.153 Uiso 1 1 calc R U . . .
C15 C 0.81590(15) 0.4484(2) 0.33094(12) 0.0486(5) Uani 1 1 d . . . . .
C16 C 0.84278(19) 0.5943(2) 0.34187(15) 0.0640(6) Uani 1 1 d . . . . .
H16 H 0.806268 0.651230 0.384142 0.077 Uiso 1 1 calc R U . . .
C17 C 0.9231(2) 0.6558(3) 0.29065(19) 0.0841(8) Uani 1 1 d . . . . .
H17 H 0.941850 0.753433 0.299481 0.101 Uiso 1 1 calc R U . . .
C18 C 0.9758(2) 0.5739(4) 0.2266(2) 0.0876(9) Uani 1 1 d . . . . .
H18 H 1.031060 0.615434 0.192865 0.105 Uiso 1 1 calc R U . . .
C19 C 0.9468(2) 0.4301(3) 0.21235(17) 0.0825(8) Uani 1 1 d . . . . .
H19 H 0.980891 0.375025 0.167712 0.099 Uiso 1 1 calc R U . . .
C20 C 0.86743(18) 0.3683(3) 0.26419(14) 0.0657(6) Uani 1 1 d . . . . .
H20 H 0.847987 0.271109 0.254311 0.079 Uiso 1 1 calc R U . . .
N1 N 0.56265(15) 0.51779(18) 0.32647(11) 0.0609(5) Uani 1 1 d . . . . .
N2 N 0.55674(14) 0.33944(18) 0.43306(11) 0.0574(5) Uani 1 1 d . . . . .
O1 O 0.58637(15) 0.13297(19) 0.51993(11) 0.0890(6) Uani 1 1 d . . . . .
C2 C 0.2659(13) 0.471(3) 0.3455(19) 0.103(4) Uani 0.57(9) 1 d D U P C 1
H2 H 0.200339 0.507492 0.323052 0.123 Uiso 0.57(9) 1 calc R U P C 1
C3 C 0.2572(14) 0.359(3) 0.4076(18) 0.099(4) Uani 0.57(9) 1 d D U P C 1
H3 H 0.191247 0.318742 0.424465 0.119 Uiso 0.57(9) 1 calc R U P C 1
C2D C 0.2565(17) 0.495(4) 0.327(3) 0.115(5) Uani 0.43(9) 1 d D U P C 2
H2D H 0.192315 0.528282 0.300815 0.138 Uiso 0.43(9) 1 calc R U P C 2
C3D C 0.269(3) 0.385(5) 0.394(3) 0.118(6) Uani 0.43(9) 1 d D U P C 2
H3D H 0.201507 0.351468 0.412465 0.141 Uiso 0.43(9) 1 calc R U P C 2


_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 C2D 1.382(16) . ?
C1 C6 1.385(3) . ?
C1 C2 1.439(14) . ?
C1 H1 0.9300 . ?
C4 C3 1.351(13) . ?
C4 C5 1.380(3) . ?
C4 C3D 1.419(18) . ?
C4 H4 0.9300 . ?
C5 N2 1.390(3) . ?
C5 C6 1.398(3) . ?
C6 N1 1.416(3) . ?
C7 N1 1.300(2) . ?
C7 N2 1.372(2) . ?
C7 C8 1.468(3) . ?
C8 C9 1.356(2) . ?
C8 C15 1.482(3) . ?
C9 C10 1.501(3) . ?
C9 C11 1.522(3) . ?
C10 O1 1.200(2) . ?
C10 N2 1.402(3) . ?
C11 C12 1.526(4) . ?
C11 C13 1.536(3) . ?
C11 C14 1.537(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.382(3) . ?
C15 C20 1.383(3) . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C2 C3 1.377(13) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C2D C3D 1.399(17) . ?
C2D H2D 0.9300 . ?
C3D H3D 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
C2D C1 C6 125.5(18) . . ?
C6 C1 C2 111.2(12) . . ?
C6 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
C3 C4 C5 120.8(13) . . ?
C5 C4 C3D 107(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 N2 132.4(3) . . ?
C4 C5 C6 123.5(3) . . ?
N2 C5 C6 104.07(19) . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 N1 128.2(3) . . ?
C5 C6 N1 111.44(19) . . ?
N1 C7 N2 114.97(19) . . ?
N1 C7 C8 136.73(19) . . ?
N2 C7 C8 107.92(17) . . ?
C9 C8 C7 107.89(18) . . ?
C9 C8 C15 131.27(18) . . ?
C7 C8 C15 120.63(16) . . ?
C8 C9 C10 108.29(18) . . ?
C8 C9 C11 131.24(19) . . ?
C10 C9 C11 120.39(17) . . ?
O1 C10 N2 123.8(2) . . ?
O1 C10 C9 130.9(2) . . ?
N2 C10 C9 105.20(17) . . ?
C9 C11 C12 112.08(18) . . ?
C9 C11 C13 107.51(18) . . ?
C12 C11 C13 111.1(2) . . ?
C9 C11 C14 110.62(19) . . ?
C12 C11 C14 106.5(2) . . ?
C13 C11 C14 109.09(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.6(2) . . ?
C16 C15 C8 121.01(18) . . ?
C20 C15 C8 120.37(17) . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 120.9(2) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C7 N1 C6 102.80(18) . . ?
C7 N2 C5 106.64(18) . . ?
C7 N2 C10 110.49(17) . . ?
C5 N2 C10 140.9(2) . . ?
C3 C2 C1 130(2) . . ?
C3 C2 H2 114.8 . . ?
C1 C2 H2 114.8 . . ?
C4 C3 C2 114(2) . . ?
C4 C3 H3 123.1 . . ?
C2 C3 H3 123.1 . . ?
C1 C2D C3D 105(4) . . ?
C1 C2D H2D 127.3 . . ?
C3D C2D H2D 127.3 . . ?
C2D C3D C4 139(4) . . ?
C2D C3D H3D 110.7 . . ?
C4 C3D H3D 110.7 . . ?

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 C4 C5 N2 -177.0(14) . . . . ?
C3D C4 C5 N2 -177.7(17) . . . . ?
C3 C4 C5 C6 0.8(14) . . . . ?
C3D C4 C5 C6 0.1(17) . . . . ?
C2D C1 C6 C5 -2.3(18) . . . . ?
C2 C1 C6 C5 -0.1(11) . . . . ?
C2D C1 C6 N1 173.8(17) . . . . ?
C2 C1 C6 N1 176.0(11) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
N2 C5 C6 C1 178.59(18) . . . . ?
C4 C5 C6 N1 -176.43(19) . . . . ?
N2 C5 C6 N1 1.9(2) . . . . ?
N1 C7 C8 C9 -171.3(2) . . . . ?
N2 C7 C8 C9 0.9(2) . . . . ?
N1 C7 C8 C15 4.0(3) . . . . ?
N2 C7 C8 C15 176.22(15) . . . . ?
C7 C8 C9 C10 1.9(2) . . . . ?
C15 C8 C9 C10 -172.77(18) . . . . ?
C7 C8 C9 C11 178.62(19) . . . . ?
C15 C8 C9 C11 4.0(3) . . . . ?
C8 C9 C10 O1 174.2(2) . . . . ?
C11 C9 C10 O1 -2.9(3) . . . . ?
C8 C9 C10 N2 -3.9(2) . . . . ?
C11 C9 C10 N2 178.93(16) . . . . ?
C8 C9 C11 C12 21.9(3) . . . . ?
C10 C9 C11 C12 -161.7(2) . . . . ?
C8 C9 C11 C13 -100.4(3) . . . . ?
C10 C9 C11 C13 76.0(2) . . . . ?
C8 C9 C11 C14 140.6(2) . . . . ?
C10 C9 C11 C14 -43.0(3) . . . . ?
C9 C8 C15 C16 -120.7(2) . . . . ?
C7 C8 C15 C16 65.2(2) . . . . ?
C9 C8 C15 C20 61.5(3) . . . . ?
C7 C8 C15 C20 -112.6(2) . . . . ?
C20 C15 C16 C17 -3.4(3) . . . . ?
C8 C15 C16 C17 178.79(19) . . . . ?
C15 C16 C17 C18 1.5(3) . . . . ?
C16 C17 C18 C19 1.2(4) . . . . ?
C17 C18 C19 C20 -1.9(4) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C16 C15 C20 C19 2.7(3) . . . . ?
C8 C15 C20 C19 -179.49(19) . . . . ?
N2 C7 N1 C6 -1.8(2) . . . . ?
C8 C7 N1 C6 170.0(2) . . . . ?
C1 C6 N1 C7 -176.5(2) . . . . ?
C5 C6 N1 C7 -0.1(2) . . . . ?
N1 C7 N2 C5 3.1(2) . . . . ?
C8 C7 N2 C5 -170.99(15) . . . . ?
N1 C7 N2 C10 170.59(15) . . . . ?
C8 C7 N2 C10 -3.5(2) . . . . ?
C4 C5 N2 C7 175.3(2) . . . . ?
C6 C5 N2 C7 -2.8(2) . . . . ?
C4 C5 N2 C10 14.0(4) . . . . ?
C6 C5 N2 C10 -164.1(2) . . . . ?
O1 C10 N2 C7 -173.78(18) . . . . ?
C9 C10 N2 C7 4.5(2) . . . . ?
O1 C10 N2 C5 -13.0(4) . . . . ?
C9 C10 N2 C5 165.3(2) . . . . ?
C6 C1 C2 C3 -1(3) . . . . ?
C5 C4 C3 C2 -2(2) . . . . ?
C1 C2 C3 C4 2(3) . . . . ?
C6 C1 C2D C3D 3(3) . . . . ?
C1 C2D C3D C4 -3(5) . . . . ?
C5 C4 C3D C2D 2(5) . . . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.027

