# 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_ortho2_a
_database_code_depnum_ccdc_archive 'CCDC 2478016'
loop_
_audit_author_name
_audit_author_address
'P Das'
;Asutosh College, University of Calcutta
India
;
_audit_update_record             
;
2025-08-02 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2025-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 O2'
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.7159(2)
_cell_length_b                   7.12150(10)
_cell_length_c                   30.6961(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2342.52(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9561
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      67.98
_cell_measurement_theta_min      2.88
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6107
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1216 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.8109.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            45244
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         2.879
_diffrn_ambient_temperature      299.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2077
_reflns_number_total             2146
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      0.931
_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)+(0.0780P)²+0.7447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1170
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B)
1.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G)
1.c Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J)
1.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.53847(8) 0.61566(13) 0.44728(3) 0.0386(3) Uani 1 1 d . . . . .
H001 H 0.479963 0.689870 0.447073 0.058 Uiso 1 1 calc R U . . .
O002 O 0.18090(9) 0.31793(15) 0.45151(3) 0.0476(3) Uani 1 1 d . . . . .
N003 N 0.38999(10) 0.37670(16) 0.45981(4) 0.0373(3) Uani 1 1 d . . . . .
C004 C 0.49588(12) 0.43563(18) 0.43382(4) 0.0342(3) Uani 1 1 d . . . . .
C005 C 0.31740(12) 0.40024(18) 0.39105(4) 0.0366(3) Uani 1 1 d . . . . .
C006 C 0.43965(11) 0.44234(17) 0.38777(4) 0.0348(3) Uani 1 1 d . . . . .
C007 C 0.28401(12) 0.35946(18) 0.43726(4) 0.0354(3) Uani 1 1 d . . . . .
C008 C 0.51361(12) 0.4868(2) 0.34903(4) 0.0386(3) Uani 1 1 d . . . . .
C009 C 0.60551(12) 0.3006(2) 0.43816(5) 0.0431(4) Uani 1 1 d . . . . .
H00A H 0.673438 0.345075 0.420001 0.052 Uiso 1 1 calc R U . . .
H00B H 0.634255 0.301763 0.468118 0.052 Uiso 1 1 calc R U . . .
C00A C 0.22343(13) 0.4023(2) 0.35816(5) 0.0464(4) Uani 1 1 d . . . . .
N00B N 0.14503(14) 0.4065(3) 0.33314(5) 0.0740(5) Uani 1 1 d . . . . .
C00C C 0.48051(15) 0.4123(2) 0.30859(5) 0.0508(4) Uani 1 1 d . . . . .
H00C H 0.410914 0.334911 0.306311 0.061 Uiso 1 1 calc R U . . .
C00D C 0.61907(14) 0.6001(2) 0.35152(5) 0.0496(4) Uani 1 1 d . . . . .
H00D H 0.643323 0.649753 0.378238 0.060 Uiso 1 1 calc R U . . .
C00E C 0.55053(16) 0.4527(3) 0.27178(5) 0.0598(4) Uani 1 1 d . . . . .
H00E H 0.527582 0.402635 0.244967 0.072 Uiso 1 1 calc R U . . .
C00F C 0.68800(16) 0.6395(3) 0.31467(6) 0.0597(4) Uani 1 1 d . . . . .
H00F H 0.758157 0.715886 0.316712 0.072 Uiso 1 1 calc R U . . .
C00G C 0.65360(16) 0.5664(3) 0.27478(5) 0.0593(4) Uani 1 1 d . . . . .
H00G H 0.700128 0.594076 0.250022 0.071 Uiso 1 1 calc R U . . .
C00H C 0.57493(18) 0.1010(2) 0.42545(8) 0.0717(6) Uani 1 1 d . . . . .
H00H H 0.557508 0.095588 0.394802 0.107 Uiso 1 1 calc R U . . .
H00I H 0.503153 0.059263 0.441462 0.107 Uiso 1 1 calc R U . . .
H00J H 0.644696 0.021329 0.432018 0.107 Uiso 1 1 calc R U . . .
H003 H 0.3925(16) 0.367(3) 0.4873(6) 0.053(5) 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
O001 H001 0.8200 . ?
O001 C004 1.4223(16) . ?
O002 C007 1.2246(16) . ?
N003 C004 1.4491(16) . ?
N003 C007 1.3356(17) . ?
N003 H003 0.846(19) . ?
C004 C006 1.5372(16) . ?
C004 C009 1.5241(18) . ?
C005 C006 1.3477(18) . ?
C005 C007 1.4915(17) . ?
C005 C00A 1.4260(18) . ?
C006 C008 1.4637(18) . ?
C008 C00C 1.3961(19) . ?
C008 C00D 1.391(2) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C00H 1.510(2) . ?
C00A N00B 1.1387(19) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.387(2) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.380(2) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.373(3) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.381(3) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?

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
C004 O001 H001 109.5 . . ?
C004 N003 H003 123.1(12) . . ?
C007 N003 C004 114.02(11) . . ?
C007 N003 H003 122.4(12) . . ?
O001 C004 N003 110.63(10) . . ?
O001 C004 C006 111.40(10) . . ?
O001 C004 C009 107.23(10) . . ?
N003 C004 C006 102.02(9) . . ?
N003 C004 C009 111.88(11) . . ?
C009 C004 C006 113.70(11) . . ?
C006 C005 C007 110.34(10) . . ?
C006 C005 C00A 129.15(12) . . ?
C00A C005 C007 120.39(12) . . ?
C005 C006 C004 107.78(10) . . ?
C005 C006 C008 129.43(11) . . ?
C008 C006 C004 122.79(11) . . ?
O002 C007 N003 127.17(12) . . ?
O002 C007 C005 127.10(12) . . ?
N003 C007 C005 105.72(10) . . ?
C00C C008 C006 120.18(12) . . ?
C00D C008 C006 121.39(12) . . ?
C00D C008 C00C 118.41(13) . . ?
C004 C009 H00A 108.8 . . ?
C004 C009 H00B 108.8 . . ?
H00A C009 H00B 107.7 . . ?
C00H C009 C004 113.84(12) . . ?
C00H C009 H00A 108.8 . . ?
C00H C009 H00B 108.8 . . ?
N00B C00A C005 177.20(18) . . ?
C008 C00C H00C 119.7 . . ?
C00E C00C C008 120.56(15) . . ?
C00E C00C H00C 119.7 . . ?
C008 C00D H00D 119.7 . . ?
C00F C00D C008 120.52(14) . . ?
C00F C00D H00D 119.7 . . ?
C00C C00E H00E 119.9 . . ?
C00G C00E C00C 120.21(15) . . ?
C00G C00E H00E 119.9 . . ?
C00D C00F H00F 119.8 . . ?
C00D C00F C00G 120.50(15) . . ?
C00G C00F H00F 119.8 . . ?
C00E C00G C00F 119.79(14) . . ?
C00E C00G H00G 120.1 . . ?
C00F C00G H00G 120.1 . . ?
C009 C00H H00H 109.5 . . ?
C009 C00H H00I 109.5 . . ?
C009 C00H H00J 109.5 . . ?
H00H C00H H00I 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?

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
O001 C004 C006 C005 -115.33(12) . . . . ?
O001 C004 C006 C008 65.03(15) . . . . ?
O001 C004 C009 C00H 179.37(14) . . . . ?
N003 C004 C006 C005 2.73(13) . . . . ?
N003 C004 C006 C008 -176.91(12) . . . . ?
N003 C004 C009 C00H 57.90(17) . . . . ?
C004 N003 C007 O002 -177.46(13) . . . . ?
C004 N003 C007 C005 2.86(15) . . . . ?
C004 C006 C008 C00C 150.62(14) . . . . ?
C004 C006 C008 C00D -28.1(2) . . . . ?
C005 C006 C008 C00C -28.9(2) . . . . ?
C005 C006 C008 C00D 152.35(15) . . . . ?
C006 C004 C009 C00H -57.03(18) . . . . ?
C006 C005 C007 O002 179.44(13) . . . . ?
C006 C005 C007 N003 -0.88(15) . . . . ?
C006 C008 C00C C00E -179.57(14) . . . . ?
C006 C008 C00D C00F 179.60(15) . . . . ?
C007 N003 C004 O001 115.12(12) . . . . ?
C007 N003 C004 C006 -3.50(14) . . . . ?
C007 N003 C004 C009 -125.40(12) . . . . ?
C007 C005 C006 C004 -1.25(14) . . . . ?
C007 C005 C006 C008 178.35(13) . . . . ?
C008 C00C C00E C00G 0.2(3) . . . . ?
C008 C00D C00F C00G -0.3(3) . . . . ?
C009 C004 C006 C005 123.37(12) . . . . ?
C009 C004 C006 C008 -56.27(16) . . . . ?
C00A C005 C006 C004 174.64(14) . . . . ?
C00A C005 C006 C008 -5.8(2) . . . . ?
C00A C005 C007 O002 3.1(2) . . . . ?
C00A C005 C007 N003 -177.18(12) . . . . ?
C00C C008 C00D C00F 0.9(2) . . . . ?
C00C C00E C00G C00F 0.5(3) . . . . ?
C00D C008 C00C C00E -0.8(2) . . . . ?
C00D C00F C00G C00E -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
