# Supplementary Information (SI) for ChemComm.
# 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_j_a
_database_code_depnum_ccdc_archive 'CCDC 2382549'
loop_
_audit_author_name
_audit_author_address
'SHUBHAJIT BASAK'
;INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI
India
;
_audit_update_record             
;
2024-09-08 deposited with the CCDC.	2024-12-19 downloaded from the CCDC.
;
_audit_creation_date             2024-03-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N2 O3'
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7677(7)
_cell_length_b                   9.1717(8)
_cell_length_c                   10.1712(9)
_cell_angle_alpha                64.119(2)
_cell_angle_beta                 76.342(2)
_cell_angle_gamma                77.008(2)
_cell_volume                     708.10(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6913
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1109 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.9365.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15278
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.414
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1921
_reflns_number_total             2456
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.189
_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)+(0.0204P)²+0.5071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1161
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C15(H15), C1(H1), C4(H4), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.8110(2) 0.6235(2) 0.20026(18) 0.0541(5) Uani 1 1 d . . . . .
O3 O 0.9281(2) 0.8010(2) 0.70266(18) 0.0494(5) Uani 1 1 d . . . . .
O1 O 0.6118(2) 0.2019(2) 0.58695(19) 0.0536(5) Uani 1 1 d . . . . .
N1 N 0.5875(2) 0.3615(2) 0.9002(2) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.7103(2) 0.4189(2) 0.4046(2) 0.0377(5) Uani 1 1 d . . . . .
C12 C 0.7749(3) 0.5335(3) 0.5924(2) 0.0325(5) Uani 1 1 d . . . . .
C5 C 0.6693(3) 0.2828(3) 0.8153(3) 0.0356(6) Uani 1 1 d . . . . .
C6 C 0.7045(3) 0.3836(3) 0.6539(2) 0.0344(6) Uani 1 1 d . . . . .
C11 C 0.8102(3) 0.6195(3) 0.4373(2) 0.0345(6) Uani 1 1 d . . . . .
C10 C 0.7799(3) 0.5601(3) 0.3354(3) 0.0385(6) Uani 1 1 d . . . . .
C13 C 0.8147(3) 0.5952(3) 0.6832(3) 0.0353(6) Uani 1 1 d . . . . .
H13 H 0.793942 0.540169 0.785601 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6772(3) 0.3360(3) 0.5546(3) 0.0367(6) Uani 1 1 d . . . . .
C16 C 0.8801(3) 0.7624(3) 0.3790(3) 0.0408(6) Uani 1 1 d . . . . .
H16 H 0.902874 0.818498 0.276924 0.049 Uiso 1 1 calc R U . . .
C14 C 0.8837(3) 0.7353(3) 0.6221(3) 0.0377(6) Uani 1 1 d . . . . .
C15 C 0.9154(3) 0.8212(3) 0.4688(3) 0.0424(6) Uani 1 1 d . . . . .
H15 H 0.960231 0.917401 0.428360 0.051 Uiso 1 1 calc R U . . .
C1 C 0.5540(3) 0.2715(3) 1.0453(3) 0.0498(7) Uani 1 1 d . . . . .
H1 H 0.497376 0.324616 1.105373 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7186(3) 0.1159(3) 0.8739(3) 0.0490(7) Uani 1 1 d . . . . .
H4 H 0.776187 0.064690 0.812566 0.059 Uiso 1 1 calc R U . . .
C2 C 0.5978(4) 0.1060(3) 1.1108(3) 0.0589(8) Uani 1 1 d . . . . .
H2 H 0.571159 0.048607 1.212363 0.071 Uiso 1 1 calc R U . . .
C9 C 0.6677(3) 0.3371(3) 0.3261(3) 0.0480(7) Uani 1 1 d . . . . .
H9A H 0.760169 0.301709 0.267409 0.058 Uiso 1 1 calc R U . . .
H9B H 0.590401 0.407503 0.262491 0.058 Uiso 1 1 calc R U . . .
C17 C 0.9071(4) 0.7143(3) 0.8602(3) 0.0541(7) Uani 1 1 d . . . . .
H17A H 0.959172 0.603740 0.885446 0.081 Uiso 1 1 calc R U . . .
H17B H 0.796073 0.713642 0.898489 0.081 Uiso 1 1 calc R U . . .
H17C H 0.952109 0.767211 0.902229 0.081 Uiso 1 1 calc R U . . .
C3 C 0.6822(4) 0.0263(3) 1.0232(3) 0.0605(8) Uani 1 1 d . . . . .
H3 H 0.713971 -0.086082 1.064237 0.073 Uiso 1 1 calc R U . . .
C8 C 0.5982(3) 0.1933(3) 0.4522(3) 0.0510(7) Uani 1 1 d . . . . .
H8A H 0.487901 0.198740 0.447037 0.061 Uiso 1 1 calc R U . . .
H8B H 0.655762 0.091460 0.448062 0.061 Uiso 1 1 calc R U . . .


_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
O2 C10 1.224(3) . ?
O3 C14 1.369(3) . ?
O3 C17 1.431(3) . ?
O1 C7 1.351(3) . ?
O1 C8 1.440(3) . ?
N1 C5 1.342(3) . ?
N1 C1 1.336(3) . ?
N2 C10 1.379(3) . ?
N2 C7 1.366(3) . ?
N2 C9 1.460(3) . ?
C12 C6 1.453(3) . ?
C12 C11 1.414(3) . ?
C12 C13 1.411(3) . ?
C5 C6 1.486(3) . ?
C5 C4 1.383(3) . ?
C6 C7 1.347(3) . ?
C11 C10 1.459(3) . ?
C11 C16 1.398(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.363(3) . ?
C14 C15 1.397(3) . ?
C15 H15 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.368(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.508(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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
C14 O3 C17 117.89(19) . . ?
C7 O1 C8 109.78(19) . . ?
C1 N1 C5 117.2(2) . . ?
C10 N2 C9 123.9(2) . . ?
C7 N2 C10 124.3(2) . . ?
C7 N2 C9 111.8(2) . . ?
C11 C12 C6 120.0(2) . . ?
C13 C12 C6 122.0(2) . . ?
C13 C12 C11 118.0(2) . . ?
N1 C5 C6 116.8(2) . . ?
N1 C5 C4 122.0(2) . . ?
C4 C5 C6 121.2(2) . . ?
C12 C6 C5 123.4(2) . . ?
C7 C6 C12 115.8(2) . . ?
C7 C6 C5 120.8(2) . . ?
C12 C11 C10 121.6(2) . . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 C10 118.7(2) . . ?
O2 C10 N2 120.1(2) . . ?
O2 C10 C11 126.0(2) . . ?
N2 C10 C11 113.8(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
O1 C7 N2 109.8(2) . . ?
C6 C7 O1 125.7(2) . . ?
C6 C7 N2 124.5(2) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
O3 C14 C13 124.1(2) . . ?
O3 C14 C15 114.9(2) . . ?
C13 C14 C15 121.0(2) . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.0(3) . . ?
C2 C1 H1 118.0 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
N2 C9 H9A 111.4 . . ?
N2 C9 H9B 111.4 . . ?
N2 C9 C8 101.7(2) . . ?
H9A C9 H9B 109.3 . . ?
C8 C9 H9A 111.4 . . ?
C8 C9 H9B 111.4 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
O1 C8 C9 106.9(2) . . ?
O1 C8 H8A 110.4 . . ?
O1 C8 H8B 110.4 . . ?
C9 C8 H8A 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?

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
O3 C14 C15 C16 177.9(2) . . . . ?
N1 C5 C6 C12 50.4(3) . . . . ?
N1 C5 C6 C7 -132.1(2) . . . . ?
N1 C5 C4 C3 0.7(4) . . . . ?
N1 C1 C2 C3 0.3(5) . . . . ?
N2 C9 C8 O1 -1.9(3) . . . . ?
C12 C6 C7 O1 -179.5(2) . . . . ?
C12 C6 C7 N2 -0.4(3) . . . . ?
C12 C11 C10 O2 -177.6(2) . . . . ?
C12 C11 C10 N2 2.1(3) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
C12 C13 C14 O3 -178.8(2) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C5 N1 C1 C2 0.0(4) . . . . ?
C5 C6 C7 O1 2.8(4) . . . . ?
C5 C6 C7 N2 -178.1(2) . . . . ?
C5 C4 C3 C2 -0.4(4) . . . . ?
C6 C12 C11 C10 -1.0(3) . . . . ?
C6 C12 C11 C16 -179.1(2) . . . . ?
C6 C12 C13 C14 178.8(2) . . . . ?
C6 C5 C4 C3 -179.1(3) . . . . ?
C11 C12 C6 C5 177.7(2) . . . . ?
C11 C12 C6 C7 0.1(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C11 C16 C15 C14 1.1(4) . . . . ?
C10 N2 C7 O1 -179.0(2) . . . . ?
C10 N2 C7 C6 1.8(4) . . . . ?
C10 N2 C9 C8 179.9(2) . . . . ?
C10 C11 C16 C15 -178.1(2) . . . . ?
C13 C12 C6 C5 -0.3(3) . . . . ?
C13 C12 C6 C7 -178.0(2) . . . . ?
C13 C12 C11 C10 177.1(2) . . . . ?
C13 C12 C11 C16 -1.0(3) . . . . ?
C13 C14 C15 C16 -1.3(4) . . . . ?
C7 O1 C8 C9 1.6(3) . . . . ?
C7 N2 C10 O2 177.2(2) . . . . ?
C7 N2 C10 C11 -2.5(3) . . . . ?
C7 N2 C9 C8 1.7(3) . . . . ?
C16 C11 C10 O2 0.5(4) . . . . ?
C16 C11 C10 N2 -179.8(2) . . . . ?
C1 N1 C5 C6 179.4(2) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C4 C5 C6 C12 -129.7(3) . . . . ?
C4 C5 C6 C7 47.8(3) . . . . ?
C9 N2 C10 O2 -0.7(4) . . . . ?
C9 N2 C10 C11 179.6(2) . . . . ?
C9 N2 C7 O1 -0.9(3) . . . . ?
C9 N2 C7 C6 179.9(2) . . . . ?
C17 O3 C14 C13 2.7(4) . . . . ?
C17 O3 C14 C15 -176.6(2) . . . . ?
C8 O1 C7 N2 -0.5(3) . . . . ?
C8 O1 C7 C6 178.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
