# Supplementary Information (SI) for Journal of Materials Chemistry B.
# 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_8auga_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2414593'
loop_
_audit_author_name
_audit_author_address
'Parkhi '
;Indian Institute of Technology Kanpur
India
;
_audit_update_record             
;
2025-01-05 deposited with the CCDC.	2025-05-22 downloaded from the CCDC.
;
_audit_creation_date             2024-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_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                   7.6488(3)
_cell_length_b                   8.2023(3)
_cell_length_c                   10.7408(4)
_cell_angle_alpha                78.9550(10)
_cell_angle_beta                 78.4510(10)
_cell_angle_gamma                76.2820(10)
_cell_volume                     633.98(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5205
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      3.13
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0400 after correction.
The Ratio of minimum to maximum transmission is 0.8970.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10951
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         2.586
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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           1.0
_diffrn_source_power             0.05
_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                2668
_reflns_number_total             3147
_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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.3002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1012
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
1.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), N1(H1), C14(H14), C4(H4), C10(H10), C7(H7), C12(H12), C8(H8),
 C13(H13), C2(H2B), C3(H3)
1.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O2 O 0.00753(12) 1.26460(11) -0.00053(9) 0.0213(2) Uani 1 1 d . . . . .
H2 H -0.028644 1.178013 -0.007002 0.032 Uiso 1 1 calc R U . . .
N2 N 0.34576(13) 0.71907(13) 0.24674(9) 0.0144(2) Uani 1 1 d . . . . .
H2A H 0.245337 0.742712 0.212843 0.017 Uiso 1 1 calc R U . . .
N1 N 0.14610(14) 0.19080(13) 0.68248(10) 0.0162(2) Uani 1 1 d . . . . .
H1 H 0.090313 0.147089 0.756806 0.019 Uiso 1 1 calc R U . . .
C5 C 0.27860(15) 0.53778(14) 0.45523(11) 0.0130(2) Uani 1 1 d . . . . .
C11 C 0.38645(16) 1.00093(15) 0.15718(11) 0.0140(2) Uani 1 1 d . . . . .
C15 C 0.16992(16) 1.21623(15) 0.04394(11) 0.0159(2) Uani 1 1 d . . . . .
C16 C 0.21876(16) 1.04571(15) 0.10824(11) 0.0140(2) Uani 1 1 d . . . . .
C1 C 0.14997(15) 0.36023(15) 0.64353(11) 0.0141(2) Uani 1 1 d . . . . .
C14 C 0.28199(17) 1.32919(15) 0.02848(11) 0.0179(3) Uani 1 1 d . . . . .
H14 H 0.246342 1.441530 -0.014197 0.022 Uiso 1 1 calc R U . . .
C4 C 0.19770(16) 0.67635(15) 0.51767(11) 0.0160(2) Uani 1 1 d . . . . .
H4 H 0.210873 0.786672 0.475435 0.019 Uiso 1 1 calc R U . . .
C10 C 0.44148(16) 0.83587(15) 0.22554(11) 0.0144(2) Uani 1 1 d . . . . .
H10 H 0.553818 0.809691 0.257294 0.017 Uiso 1 1 calc R U . . .
C6 C 0.25538(15) 0.37584(15) 0.51922(11) 0.0134(2) Uani 1 1 d . . . . .
C7 C 0.31465(16) 0.20834(15) 0.48520(12) 0.0163(2) Uani 1 1 d . . . . .
H7 H 0.388778 0.177794 0.407595 0.020 Uiso 1 1 calc R U . . .
C12 C 0.50127(17) 1.11977(15) 0.13834(11) 0.0163(2) Uani 1 1 d . . . . .
H12 H 0.614138 1.087396 0.169682 0.020 Uiso 1 1 calc R U . . .
C8 C 0.24378(17) 0.10132(15) 0.58610(12) 0.0177(2) Uani 1 1 d . . . . .
H8 H 0.259675 -0.017748 0.589228 0.021 Uiso 1 1 calc R U . . .
C9 C 0.39211(16) 0.55166(14) 0.32248(11) 0.0148(2) Uani 1 1 d . . . . .
H9A H 0.522689 0.527473 0.330836 0.018 Uiso 1 1 calc R U . . .
H9B H 0.373762 0.464923 0.276459 0.018 Uiso 1 1 calc R U . . .
C13 C 0.44983(17) 1.28058(15) 0.07523(11) 0.0179(3) Uani 1 1 d . . . . .
H13 H 0.526948 1.359587 0.062829 0.021 Uiso 1 1 calc R U . . .
C2 C 0.07131(16) 0.49995(16) 0.70768(11) 0.0169(2) Uani 1 1 d . . . . .
H2B H 0.003853 0.487187 0.792173 0.020 Uiso 1 1 calc R U . . .
C3 C 0.09627(17) 0.65726(16) 0.64247(12) 0.0181(3) Uani 1 1 d . . . . .
H3 H 0.043716 0.754992 0.682820 0.022 Uiso 1 1 calc R U . . .
O1 O 0.11098(11) 0.94127(11) 0.11932(8) 0.0174(2) 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
O2 H2 0.8400 . ?
O2 C15 1.3636(15) . ?
N2 H2A 0.8800 . ?
N2 C10 1.2992(15) . ?
N2 C9 1.4593(14) . ?
N1 H1 0.8800 . ?
N1 C1 1.3780(15) . ?
N1 C8 1.3748(16) . ?
C5 C4 1.3845(16) . ?
C5 C6 1.4076(16) . ?
C5 C9 1.5128(16) . ?
C11 C16 1.4244(16) . ?
C11 C10 1.4219(16) . ?
C11 C12 1.4219(16) . ?
C15 C16 1.4346(16) . ?
C15 C14 1.3717(17) . ?
C16 O1 1.2978(14) . ?
C1 C6 1.4147(16) . ?
C1 C2 1.3999(17) . ?
C14 H14 0.9500 . ?
C14 C13 1.4134(18) . ?
C4 H4 0.9500 . ?
C4 C3 1.4086(17) . ?
C10 H10 0.9500 . ?
C6 C7 1.4343(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3655(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3682(17) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C13 H13 0.9500 . ?
C2 H2B 0.9500 . ?
C2 C3 1.3816(17) . ?
C3 H3 0.9500 . ?

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
C15 O2 H2 109.5 . . ?
C10 N2 H2A 117.5 . . ?
C10 N2 C9 124.97(10) . . ?
C9 N2 H2A 117.5 . . ?
C1 N1 H1 125.6 . . ?
C8 N1 H1 125.6 . . ?
C8 N1 C1 108.75(10) . . ?
C4 C5 C6 118.23(10) . . ?
C4 C5 C9 123.28(10) . . ?
C6 C5 C9 118.49(10) . . ?
C10 C11 C16 120.23(10) . . ?
C10 C11 C12 119.05(11) . . ?
C12 C11 C16 120.73(10) . . ?
O2 C15 C16 118.33(10) . . ?
O2 C15 C14 120.46(11) . . ?
C14 C15 C16 121.20(11) . . ?
C11 C16 C15 116.92(10) . . ?
O1 C16 C11 123.48(10) . . ?
O1 C16 C15 119.60(10) . . ?
N1 C1 C6 107.49(10) . . ?
N1 C1 C2 130.09(11) . . ?
C2 C1 C6 122.41(11) . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C13 120.84(11) . . ?
C13 C14 H14 119.6 . . ?
C5 C4 H4 119.3 . . ?
C5 C4 C3 121.42(11) . . ?
C3 C4 H4 119.3 . . ?
N2 C10 C11 123.26(11) . . ?
N2 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C5 C6 C1 119.32(11) . . ?
C5 C6 C7 133.74(11) . . ?
C1 C6 C7 106.93(10) . . ?
C6 C7 H7 126.7 . . ?
C8 C7 C6 106.64(11) . . ?
C8 C7 H7 126.7 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.25(11) . . ?
C13 C12 H12 119.9 . . ?
N1 C8 H8 124.9 . . ?
C7 C8 N1 110.18(11) . . ?
C7 C8 H8 124.9 . . ?
N2 C9 C5 112.61(9) . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
C5 C9 H9A 109.1 . . ?
C5 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.03(11) . . ?
C12 C13 H13 120.0 . . ?
C1 C2 H2B 121.5 . . ?
C3 C2 C1 116.94(11) . . ?
C3 C2 H2B 121.5 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.64(11) . . ?
C2 C3 H3 119.2 . . ?

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
O2 C15 C16 C11 -178.02(10) . . . . ?
O2 C15 C16 O1 1.89(16) . . . . ?
O2 C15 C14 C13 179.46(11) . . . . ?
N1 C1 C6 C5 178.77(10) . . . . ?
N1 C1 C6 C7 0.01(13) . . . . ?
N1 C1 C2 C3 -178.92(12) . . . . ?
C5 C4 C3 C2 -0.68(19) . . . . ?
C5 C6 C7 C8 -177.89(12) . . . . ?
C11 C12 C13 C14 0.01(18) . . . . ?
C15 C14 C13 C12 -0.87(18) . . . . ?
C16 C11 C10 N2 0.19(18) . . . . ?
C16 C11 C12 C13 1.51(17) . . . . ?
C16 C15 C14 C13 0.22(18) . . . . ?
C1 N1 C8 C7 1.06(14) . . . . ?
C1 C6 C7 C8 0.62(13) . . . . ?
C1 C2 C3 C4 -0.62(18) . . . . ?
C14 C15 C16 C11 1.24(17) . . . . ?
C14 C15 C16 O1 -178.85(11) . . . . ?
C4 C5 C6 C1 0.52(16) . . . . ?
C4 C5 C6 C7 178.88(12) . . . . ?
C4 C5 C9 N2 -24.75(16) . . . . ?
C10 N2 C9 C5 103.14(13) . . . . ?
C10 C11 C16 C15 178.06(10) . . . . ?
C10 C11 C16 O1 -1.84(17) . . . . ?
C10 C11 C12 C13 -178.64(11) . . . . ?
C6 C5 C4 C3 0.71(17) . . . . ?
C6 C5 C9 N2 155.92(10) . . . . ?
C6 C1 C2 C3 1.90(17) . . . . ?
C6 C7 C8 N1 -1.03(14) . . . . ?
C12 C11 C16 C15 -2.08(16) . . . . ?
C12 C11 C16 O1 178.01(11) . . . . ?
C12 C11 C10 N2 -179.67(11) . . . . ?
C8 N1 C1 C6 -0.64(13) . . . . ?
C8 N1 C1 C2 -179.91(12) . . . . ?
C9 N2 C10 C11 -176.36(10) . . . . ?
C9 C5 C4 C3 -178.62(11) . . . . ?
C9 C5 C6 C1 179.89(10) . . . . ?
C9 C5 C6 C7 -1.75(19) . . . . ?
C2 C1 C6 C5 -1.88(17) . . . . ?
C2 C1 C6 C7 179.35(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
