# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2369192'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2024-07-09 deposited with the CCDC.	2025-02-17 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         'C19 H18 N2 O'
_chemical_formula_sum            'C19 H18 N2 O'
_chemical_formula_weight         290.35

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           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   13.302(4)
_cell_length_b                   5.6532(15)
_cell_length_c                   21.875(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.777(9)
_cell_angle_gamma                90
_cell_volume                     1597.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    8799
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      30.36
_exptl_crystal_description       ROD
_exptl_crystal_colour            yellow



_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6852
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32862
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.154
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2968
_reflns_number_gt                2231
_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       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'

_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.0742P)²+1.1463P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2968
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1719
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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
C1 C 0.7750(2) 0.0344(5) 0.62310(13) 0.0456(6) Uani 1 1 d . . . . .
C2 C 0.8438(2) -0.0268(6) 0.58604(15) 0.0571(8) Uani 1 1 d . . . . .
H2 H 0.881485 -0.166500 0.594424 0.069 Uiso 1 1 calc R U . . .
C3 C 0.8565(2) 0.1149(6) 0.53791(14) 0.0603(8) Uani 1 1 d . . . . .
H3 H 0.902357 0.069667 0.513919 0.072 Uiso 1 1 calc R U . . .
C4 C 0.8024(3) 0.3242(6) 0.52428(14) 0.0617(8) Uani 1 1 d . . . . .
H4 H 0.811417 0.420033 0.491443 0.074 Uiso 1 1 calc R U . . .
C5 C 0.7345(2) 0.3886(5) 0.56047(13) 0.0527(7) Uani 1 1 d . . . . .
H5 H 0.697720 0.529414 0.551934 0.063 Uiso 1 1 calc R U . . .
C6 C 0.72086(18) 0.2467(5) 0.60886(11) 0.0382(6) Uani 1 1 d . . . . .
C7 C 0.55165(19) 0.3029(5) 0.63450(11) 0.0393(6) Uani 1 1 d . . . . .
C8 C 0.4972(2) 0.2064(7) 0.57135(14) 0.0691(10) Uani 1 1 d . . . . .
H8A H 0.482878 0.335404 0.541290 0.083 Uiso 1 1 calc R U . . .
H8B H 0.542769 0.096033 0.557274 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3979(3) 0.0836(8) 0.57198(17) 0.0815(12) Uani 1 1 d . . . . .
H9A H 0.358239 0.061450 0.529027 0.098 Uiso 1 1 calc R U . . .
H9B H 0.413115 -0.071466 0.590931 0.098 Uiso 1 1 calc R U . . .
C10 C 0.3349(2) 0.2194(7) 0.60756(14) 0.0639(9) Uani 1 1 d . . . . .
H10 H 0.263058 0.209082 0.596049 0.077 Uiso 1 1 calc R U . . .
C11 C 0.3801(2) 0.3541(5) 0.65527(13) 0.0498(7) Uani 1 1 d . . . . .
H11 H 0.338776 0.434595 0.677188 0.060 Uiso 1 1 calc R U . . .
C12 C 0.49274(18) 0.3833(5) 0.67545(11) 0.0388(6) Uani 1 1 d . . . . .
C13 C 0.54152(19) 0.4820(5) 0.73539(12) 0.0439(6) Uani 1 1 d . . . . .
C14 C 0.47733(19) 0.5765(5) 0.77824(12) 0.0412(6) Uani 1 1 d . . . . .
C15 C 0.4793(2) 0.4584(6) 0.83409(15) 0.0594(8) Uani 1 1 d . . . . .
H15 H 0.518111 0.320651 0.843762 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4243(3) 0.5436(7) 0.87531(16) 0.0710(10) Uani 1 1 d . . . . .
H16 H 0.425827 0.462221 0.912472 0.085 Uiso 1 1 calc R U . . .
C17 C 0.3678(2) 0.7452(7) 0.86223(15) 0.0658(9) Uani 1 1 d . . . . .
H17 H 0.329081 0.799137 0.889654 0.079 Uiso 1 1 calc R U . . .
C18 C 0.3681(3) 0.8682(6) 0.80868(16) 0.0684(9) Uani 1 1 d . . . . .
H18 H 0.331976 1.010048 0.800644 0.082 Uiso 1 1 calc R U . . .
C19 C 0.4220(2) 0.7836(6) 0.76590(14) 0.0622(9) Uani 1 1 d . . . . .
H19 H 0.420607 0.866959 0.729052 0.075 Uiso 1 1 calc R U . . .
N1 N 0.65422(16) 0.3157(4) 0.64831(11) 0.0440(6) Uani 1 1 d . . . . .
N2 N 0.7602(3) -0.1061(6) 0.67070(17) 0.0870(11) Uani 1 1 d . . . . .
O1 O 0.63755(14) 0.4888(5) 0.75626(9) 0.0706(7) Uani 1 1 d . . . . .
H1A H 0.681(2) 0.368(5) 0.6844(13) 0.040(7) Uiso 1 1 d . . . . .
H2A H 0.716(3) -0.065(7) 0.6890(18) 0.079(12) Uiso 1 1 d . . . . .
H2B H 0.801(3) -0.227(7) 0.6856(17) 0.077(11) Uiso 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
C1 N2 1.361(4) . ?
C1 C6 1.396(4) . ?
C1 C2 1.402(4) . ?
C2 C3 1.365(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.431(3) . ?
C7 N1 1.327(3) . ?
C7 C12 1.399(3) . ?
C7 C8 1.501(4) . ?
C8 C9 1.495(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.486(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.316(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.467(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.431(3) . ?
C13 O1 1.251(3) . ?
C13 C14 1.508(3) . ?
C14 C19 1.375(4) . ?
C14 C15 1.387(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N1 H1A 0.84(3) . ?
N2 H2A 0.82(4) . ?
N2 H2B 0.88(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
N2 C1 C6 120.8(3) . . ?
N2 C1 C2 122.1(3) . . ?
C6 C1 C2 117.1(3) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 N1 121.3(2) . . ?
C1 C6 N1 117.4(2) . . ?
N1 C7 C12 122.6(2) . . ?
N1 C7 C8 118.3(2) . . ?
C12 C7 C8 119.1(2) . . ?
C9 C8 C7 113.2(3) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 112.0(3) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 123.0(3) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C7 C12 C13 120.8(2) . . ?
C7 C12 C11 117.3(2) . . ?
C13 C12 C11 121.8(2) . . ?
O1 C13 C12 123.2(2) . . ?
O1 C13 C14 116.3(2) . . ?
C12 C13 C14 120.5(2) . . ?
C19 C14 C15 118.7(3) . . ?
C19 C14 C13 122.4(3) . . ?
C15 C14 C13 118.8(2) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.6(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 119.8(3) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C7 N1 C6 126.8(2) . . ?
C7 N1 H1A 114.7(18) . . ?
C6 N1 H1A 118.5(18) . . ?
C1 N2 H2A 117(3) . . ?
C1 N2 H2B 123(2) . . ?
H2A N2 H2B 119(4) . . ?

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
N2 C1 C2 C3 179.0(3) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 N1 177.4(3) . . . . ?
N2 C1 C6 C5 -179.3(3) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
N2 C1 C6 N1 3.4(4) . . . . ?
C2 C1 C6 N1 -177.2(2) . . . . ?
N1 C7 C8 C9 149.7(3) . . . . ?
C12 C7 C8 C9 -32.6(5) . . . . ?
C7 C8 C9 C10 44.5(5) . . . . ?
C8 C9 C10 C11 -30.5(5) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
N1 C7 C12 C13 -0.8(4) . . . . ?
C8 C7 C12 C13 -178.4(3) . . . . ?
N1 C7 C12 C11 -178.6(3) . . . . ?
C8 C7 C12 C11 3.7(4) . . . . ?
C10 C11 C12 C7 13.2(4) . . . . ?
C10 C11 C12 C13 -164.7(3) . . . . ?
C7 C12 C13 O1 -4.6(4) . . . . ?
C11 C12 C13 O1 173.2(3) . . . . ?
C7 C12 C13 C14 177.7(2) . . . . ?
C11 C12 C13 C14 -4.5(4) . . . . ?
O1 C13 C14 C19 110.1(3) . . . . ?
C12 C13 C14 C19 -72.0(4) . . . . ?
O1 C13 C14 C15 -65.7(4) . . . . ?
C12 C13 C14 C15 112.1(3) . . . . ?
C19 C14 C15 C16 2.0(5) . . . . ?
C13 C14 C15 C16 178.0(3) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C15 C16 C17 C18 -2.0(5) . . . . ?
C16 C17 C18 C19 2.9(5) . . . . ?
C15 C14 C19 C18 -1.1(5) . . . . ?
C13 C14 C19 C18 -176.9(3) . . . . ?
C17 C18 C19 C14 -1.4(5) . . . . ?
C12 C7 N1 C6 -177.5(3) . . . . ?
C8 C7 N1 C6 0.1(4) . . . . ?
C5 C6 N1 C7 78.4(4) . . . . ?
C1 C6 N1 C7 -104.3(3) . . . . ?

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
_geom_hbond_publ_flag
N1 H1A O1 0.84(3) 1.92(3) 2.614(3) 139(2) . yes
N1 H1A O1 0.84(3) 2.54(3) 3.199(3) 136(2) 2_656 yes
N2 H2A N1 0.82(4) 2.40(4) 2.754(4) 107(3) . yes
N2 H2B O1 0.88(4) 2.09(4) 2.934(4) 159(3) 2_646 yes

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045



