# 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. 
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data_sc_780_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2449215'
loop_
_audit_author_name
_audit_author_address
'Srinu Tothadi'
;CSIR Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2025-05-07 deposited with the CCDC.	2026-01-20 downloaded from the CCDC.
;
_audit_creation_date             2025-05-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 N O2'
_chemical_formula_sum            'C18 H11 N O2'
_chemical_formula_weight         273.28
_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                   13.3789(9)
_cell_length_b                   12.2013(8)
_cell_length_c                   8.2874(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.751(3)
_cell_angle_gamma                90
_cell_volume                     1302.04(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9363
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.079
_cell_measurement_theta_min      3.051
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1184 before and 0.0849 after correction. The Ratio of minimum to maximum transmission is 0.8425. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            70789
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.662
_diffrn_reflns_theta_min         2.300
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2329
_reflns_number_total             4013
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.137
_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)+(0.0728P)²+0.2420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.23846(12) 0.82684(12) 0.4565(2) 0.0783(5) Uani 1 1 d . . . . .
O2 O 0.41608(9) 0.79250(9) 0.68796(16) 0.0547(3) Uani 1 1 d . . . . .
N1 N 0.39969(11) 0.60981(12) 0.66066(19) 0.0510(4) Uani 1 1 d . . . . .
C1 C -0.12674(15) 0.62844(16) 0.3814(2) 0.0573(5) Uani 1 1 d . . . . .
H1 H -0.196944 0.625624 0.376675 0.069 Uiso 1 1 calc R . . . .
C2 C -0.06317(15) 0.70918(15) 0.4781(2) 0.0561(4) Uani 1 1 d . . . . .
H2 H -0.091467 0.758824 0.538604 0.067 Uiso 1 1 calc R . . . .
C3 C 0.03927(14) 0.71588(14) 0.4845(2) 0.0504(4) Uani 1 1 d . . . . .
H3 H 0.080014 0.770522 0.548361 0.060 Uiso 1 1 calc R . . . .
C4 C 0.08471(12) 0.64045(13) 0.39497(18) 0.0433(4) Uani 1 1 d . . . . .
C5 C 0.19252(13) 0.63981(14) 0.4023(2) 0.0480(4) Uani 1 1 d . . . . .
C6 C 0.26084(14) 0.73132(15) 0.4848(2) 0.0532(4) Uani 1 1 d . . . . .
C7 C 0.36055(13) 0.70439(14) 0.6099(2) 0.0486(4) Uani 1 1 d . . . . .
C8 C 0.49074(13) 0.63424(14) 0.7848(2) 0.0480(4) Uani 1 1 d . . . . .
C9 C 0.56601(15) 0.56717(17) 0.8852(3) 0.0606(5) Uani 1 1 d . . . . .
H9 H 0.562348 0.491286 0.874750 0.073 Uiso 1 1 calc R . . . .
C10 C 0.64618(15) 0.61740(19) 1.0006(3) 0.0653(5) Uani 1 1 d . . . . .
H10 H 0.697429 0.574447 1.070531 0.078 Uiso 1 1 calc R . . . .
C11 C 0.65271(14) 0.73060(19) 1.0156(3) 0.0637(5) Uani 1 1 d . . . . .
H11 H 0.708113 0.761314 1.095927 0.076 Uiso 1 1 calc R . . . .
C12 C 0.57995(14) 0.79879(17) 0.9157(2) 0.0589(5) Uani 1 1 d . . . . .
H12 H 0.584391 0.874734 0.924208 0.071 Uiso 1 1 calc R . . . .
C13 C 0.49987(12) 0.74624(14) 0.8017(2) 0.0485(4) Uani 1 1 d . . . . .
C14 C -0.08600(14) 0.55435(15) 0.2946(2) 0.0531(4) Uani 1 1 d . . . . .
H14 H -0.128489 0.500726 0.231264 0.064 Uiso 1 1 calc R . . . .
C15 C 0.02040(13) 0.55802(13) 0.29978(19) 0.0460(4) Uani 1 1 d . . . . .
C16 C 0.06429(15) 0.47914(15) 0.2148(2) 0.0557(4) Uani 1 1 d . . . . .
H16 H 0.021772 0.426384 0.149292 0.067 Uiso 1 1 calc R . . . .
C17 C 0.16761(16) 0.47902(16) 0.2271(2) 0.0602(5) Uani 1 1 d . . . . .
H17 H 0.195425 0.425756 0.171612 0.072 Uiso 1 1 calc R . . . .
C18 C 0.23220(15) 0.55887(16) 0.3230(2) 0.0568(4) Uani 1 1 d . . . . .
H18 H 0.303129 0.557051 0.333086 0.068 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 C6 1.210(2) . ?
O2 C7 1.366(2) . ?
O2 C13 1.375(2) . ?
N1 C7 1.290(2) . ?
N1 C8 1.397(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.402(3) . ?
C1 C14 1.358(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.419(2) . ?
C4 C5 1.427(2) . ?
C4 C15 1.416(2) . ?
C5 C6 1.487(2) . ?
C5 C18 1.371(2) . ?
C6 C7 1.487(2) . ?
C8 C9 1.386(3) . ?
C8 C13 1.376(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.413(2) . ?
C15 C16 1.411(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.358(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.398(3) . ?
C18 H18 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
C7 O2 C13 103.83(13) . . ?
C7 N1 C8 104.18(14) . . ?
C2 C1 H1 119.9 . . ?
C14 C1 H1 119.9 . . ?
C14 C1 C2 120.13(17) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.89(17) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.73(16) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 123.56(15) . . ?
C15 C4 C3 118.06(15) . . ?
C15 C4 C5 118.30(15) . . ?
C4 C5 C6 120.25(15) . . ?
C18 C5 C4 120.13(16) . . ?
C18 C5 C6 119.45(16) . . ?
O1 C6 C5 123.04(16) . . ?
O1 C6 C7 118.41(17) . . ?
C5 C6 C7 118.54(15) . . ?
O2 C7 C6 115.21(15) . . ?
N1 C7 O2 115.42(15) . . ?
N1 C7 C6 129.28(16) . . ?
C9 C8 N1 131.49(17) . . ?
C13 C8 N1 108.81(15) . . ?
C13 C8 C9 119.70(17) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 C8 117.24(19) . . ?
C10 C9 H9 121.4 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.69(19) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.11(19) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 H12 122.5 . . ?
C11 C12 C13 115.02(19) . . ?
C13 C12 H12 122.5 . . ?
O2 C13 C8 107.74(14) . . ?
O2 C13 C12 128.03(17) . . ?
C8 C13 C12 124.23(17) . . ?
C1 C14 H14 119.7 . . ?
C1 C14 C15 120.58(17) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C4 119.60(15) . . ?
C16 C15 C4 119.35(16) . . ?
C16 C15 C14 121.03(16) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.08(17) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.08(17) . . ?
C18 C17 H17 120.0 . . ?
C5 C18 C17 120.98(18) . . ?
C5 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?

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
O1 C6 C7 O2 3.0(3) . . . . ?
O1 C6 C7 N1 179.4(2) . . . . ?
N1 C8 C9 C10 -178.20(17) . . . . ?
N1 C8 C13 O2 -0.72(19) . . . . ?
N1 C8 C13 C12 178.75(16) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C14 C15 C4 -0.6(2) . . . . ?
C1 C14 C15 C16 177.79(16) . . . . ?
C2 C1 C14 C15 -0.4(3) . . . . ?
C2 C3 C4 C5 -177.07(15) . . . . ?
C2 C3 C4 C15 -0.3(2) . . . . ?
C3 C4 C5 C6 -10.0(2) . . . . ?
C3 C4 C5 C18 174.73(16) . . . . ?
C3 C4 C15 C14 1.0(2) . . . . ?
C3 C4 C15 C16 -177.48(14) . . . . ?
C4 C5 C6 O1 -48.3(3) . . . . ?
C4 C5 C6 C7 130.74(17) . . . . ?
C4 C5 C18 C17 3.2(3) . . . . ?
C4 C15 C16 C17 2.1(3) . . . . ?
C5 C4 C15 C14 177.92(14) . . . . ?
C5 C4 C15 C16 -0.5(2) . . . . ?
C5 C6 C7 O2 -176.09(15) . . . . ?
C5 C6 C7 N1 0.4(3) . . . . ?
C6 C5 C18 C17 -172.17(17) . . . . ?
C7 O2 C13 C8 0.58(18) . . . . ?
C7 O2 C13 C12 -178.86(18) . . . . ?
C7 N1 C8 C9 -179.96(19) . . . . ?
C7 N1 C8 C13 0.55(19) . . . . ?
C8 N1 C7 O2 -0.2(2) . . . . ?
C8 N1 C7 C6 -176.62(17) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C8 C13 O2 179.72(16) . . . . ?
C9 C8 C13 C12 -0.8(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 O2 179.12(17) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C13 O2 C7 N1 -0.3(2) . . . . ?
C13 O2 C7 C6 176.70(14) . . . . ?
C13 C8 C9 C10 1.2(3) . . . . ?
C14 C1 C2 C3 1.1(3) . . . . ?
C14 C15 C16 C17 -176.38(17) . . . . ?
C15 C4 C5 C6 173.28(15) . . . . ?
C15 C4 C5 C18 -2.0(2) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C16 C17 C18 C5 -1.7(3) . . . . ?
C18 C5 C6 O1 127.1(2) . . . . ?
C18 C5 C6 C7 -53.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
