# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_ex-ms18
_database_code_depnum_ccdc_archive 'CCDC 2366840'
loop_
_audit_author_name
_audit_author_address
'Subash Ch Sahoo'
;Panjab University
India
;
_audit_update_record             
;
2024-07-01 deposited with the CCDC.	2026-06-16 downloaded from the CCDC.
;
_audit_creation_date             2023-03-06
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 N3 O4'
_chemical_formula_sum            'C15 H17 N3 O4'
_chemical_formula_weight         303.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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                   7.2144(5)
_cell_length_b                   9.3483(7)
_cell_length_c                   11.7060(5)
_cell_angle_alpha                75.390(5)
_cell_angle_beta                 82.455(5)
_cell_angle_gamma                75.192(6)
_cell_volume                     736.68(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5420
_cell_measurement_theta_min      3.3220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8613
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.243
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00 -18.00   0.50   18.00    --   -9.95  99.00  54.00   50
  2  ω    -16.00  40.00   0.50   18.00    --   10.22 -99.00 -51.00  112
  3  ω    -16.00  52.00   0.50   18.00    --   -9.95  38.00 150.00  136
  4  ω     11.00  49.00   0.50   18.00    --   -9.95  57.00-180.00   76
  5  ω    -38.00  -4.00   0.50   18.00    --   -9.95 -38.00 -30.00   68
  6  ω    -54.00 -10.00   0.50   18.00    --   -9.95 125.00 120.00   88
  7  ω    -30.00   4.00   0.50   18.00    --   10.22 117.00  30.73   68
  8  ω    -12.00  13.00   0.50   18.00    --   10.22 -77.00 150.00   50
  9  ω     26.00  72.00   0.50   18.00    --   10.22  38.00  60.00   92
 10  ω     49.00  74.00   0.50   18.00    --   10.22  38.00 -60.00   50
 11  ω    -19.00  39.00   0.50   18.00    --   10.22 -99.00   0.00  116
 12  ω     -8.00  17.00   0.50   18.00    --   10.22  57.00 -30.00   50
 13  ω    -54.00  36.00   0.50   18.00    --   10.22 -77.00  90.00  180
 14  ω    -52.00 -26.00   0.50   18.00    --   10.22 -77.00 150.00   52
 15  ω     -3.00  30.50   0.50   18.00    --   10.22  38.00 -60.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0104035000
_diffrn_orient_matrix_UB_12      -0.0002941000
_diffrn_orient_matrix_UB_13      -0.0593515000
_diffrn_orient_matrix_UB_21      0.0911488000
_diffrn_orient_matrix_UB_22      -0.0512907000
_diffrn_orient_matrix_UB_23      -0.0018478000
_diffrn_orient_matrix_UB_31      -0.0444824000
_diffrn_orient_matrix_UB_32      -0.0621838000
_diffrn_orient_matrix_UB_33      0.0203735000
_diffrn_oxdiff_ac3_digest_frames 
;
014d31469556645131df276af12912d6350125529a3
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01ccffada43686903e11d843dbb3c74665a655
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2245
_reflns_number_total             2942
_reflns_odcompleteness_completeness 97.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.087
_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)+(0.0661P)²+0.0857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1336
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_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 0.37699(17) 0.76725(13) 0.11422(10) 0.0519(3) Uani 1 1 d . . . . .
O1 O 0.30755(18) 0.83648(12) 0.32357(12) 0.0557(4) Uani 1 1 d . . . . .
O4 O -0.00455(17) 0.79351(13) -0.00170(11) 0.0536(4) Uani 1 1 d . . . . .
N2 N 0.27998(17) 0.44684(13) 0.40492(11) 0.0349(3) Uani 1 1 d . . . . .
N1 N 0.3631(2) 0.65439(15) 0.21719(12) 0.0442(4) Uani 1 1 d . . . . .
N3 N 0.22229(19) 0.43467(15) 0.59849(12) 0.0430(4) Uani 1 1 d . . . . .
O3 O 0.2356(2) 0.62513(17) -0.06592(12) 0.0762(5) Uani 1 1 d . . . . .
C10 C 0.3121(2) 0.40051(17) 0.30094(14) 0.0367(4) Uani 1 1 d . . . . .
C5 C 0.2527(2) 0.35523(17) 0.51464(14) 0.0371(4) Uani 1 1 d . . . . .
C2 C 0.2681(2) 0.59087(17) 0.42043(15) 0.0369(4) Uani 1 1 d . . . . .
C11 C 0.3119(2) 0.52468(17) 0.19078(14) 0.0393(4) Uani 1 1 d . . . . .
H11 H 0.410338 0.485413 0.133116 0.047 Uiso 1 1 calc R . . . .
C1 C 0.3089(2) 0.70732(18) 0.31964(15) 0.0407(4) Uani 1 1 d . . . . .
C3 C 0.2332(2) 0.57860(18) 0.54082(14) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.3271(2) 0.25098(18) 0.30862(15) 0.0436(4) Uani 1 1 d . . . . .
H9 H 0.353778 0.213485 0.240355 0.052 Uiso 1 1 calc R . . . .
C6 C 0.2630(2) 0.20030(18) 0.52259(15) 0.0427(4) Uani 1 1 d . . . . .
C13 C 0.1257(3) 0.66401(19) 0.01240(15) 0.0465(4) Uani 1 1 d . . . . .
C8 C 0.3025(2) 0.15184(18) 0.41925(16) 0.0462(4) Uani 1 1 d . . . . .
H8 H 0.313629 0.049695 0.422086 0.055 Uiso 1 1 calc R . . . .
C12 C 0.1171(2) 0.5695(2) 0.13690(15) 0.0481(4) Uani 1 1 d . . . . .
H12A H 0.076528 0.478327 0.136846 0.058 Uiso 1 1 calc R . . . .
H12B H 0.022211 0.626571 0.185504 0.058 Uiso 1 1 calc R . . . .
C4 C 0.2115(3) 0.7001(2) 0.60552(17) 0.0529(5) Uani 1 1 d . . . . .
H4A H 0.086802 0.767484 0.594984 0.079 Uiso 1 1 calc GR . . . .
H4B H 0.308777 0.756148 0.575210 0.079 Uiso 1 1 calc GR . . . .
H4C H 0.224877 0.655323 0.688241 0.079 Uiso 1 1 calc GR . . . .
C7 C 0.2292(3) 0.1003(2) 0.64093(17) 0.0585(5) Uani 1 1 d . . . . .
H7A H 0.316006 0.105714 0.694388 0.088 Uiso 1 1 calc GR . . . .
H7B H 0.250744 -0.002706 0.633328 0.088 Uiso 1 1 calc GR . . . .
H7C H 0.099138 0.133400 0.671201 0.088 Uiso 1 1 calc GR . . . .
C15 C 0.5748(3) 0.7675(2) 0.0809(2) 0.0694(6) Uani 1 1 d . . . . .
H15A H 0.584539 0.843916 0.009598 0.104 Uiso 1 1 calc GR . . . .
H15B H 0.642402 0.669674 0.067629 0.104 Uiso 1 1 calc GR . . . .
H15C H 0.630255 0.788961 0.143069 0.104 Uiso 1 1 calc GR . . . .
C14 C -0.0025(4) 0.8948(2) -0.11709(18) 0.0736(6) Uani 1 1 d . . . . .
H14A H -0.009908 0.841914 -0.176167 0.110 Uiso 1 1 calc GR . . . .
H14B H 0.114329 0.929844 -0.132071 0.110 Uiso 1 1 calc GR . . . .
H14C H -0.110589 0.980222 -0.119873 0.110 Uiso 1 1 calc GR . . . .


_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 N1 1.3989(16) . ?
O2 C15 1.429(2) . ?
O1 C1 1.2173(18) . ?
O4 C13 1.317(2) . ?
O4 C14 1.442(2) . ?
N2 C10 1.3651(19) . ?
N2 C5 1.374(2) . ?
N2 C2 1.3833(19) . ?
N1 C11 1.466(2) . ?
N1 C1 1.383(2) . ?
N3 C5 1.338(2) . ?
N3 C3 1.362(2) . ?
O3 C13 1.197(2) . ?
C10 C11 1.502(2) . ?
C10 C9 1.355(2) . ?
C5 C6 1.411(2) . ?
C2 C1 1.445(2) . ?
C2 C3 1.379(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.532(2) . ?
C3 C4 1.483(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.409(2) . ?
C6 C8 1.367(2) . ?
C6 C7 1.493(2) . ?
C13 C12 1.504(2) . ?
C8 H8 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
N1 O2 C15 109.42(13) . . ?
C13 O4 C14 116.51(15) . . ?
C10 N2 C5 124.94(13) . . ?
C10 N2 C2 127.48(14) . . ?
C5 N2 C2 107.58(13) . . ?
O2 N1 C11 110.96(12) . . ?
C1 N1 O2 114.71(13) . . ?
C1 N1 C11 126.26(14) . . ?
C5 N3 C3 105.76(13) . . ?
N2 C10 C11 115.45(13) . . ?
C9 C10 N2 116.71(15) . . ?
C9 C10 C11 127.68(15) . . ?
N2 C5 C6 118.42(14) . . ?
N3 C5 N2 110.54(13) . . ?
N3 C5 C6 131.03(15) . . ?
N2 C2 C1 119.13(14) . . ?
C3 C2 N2 104.90(14) . . ?
C3 C2 C1 135.66(14) . . ?
N1 C11 C10 109.96(13) . . ?
N1 C11 H11 108.1 . . ?
N1 C11 C12 112.21(13) . . ?
C10 C11 H11 108.1 . . ?
C10 C11 C12 110.38(13) . . ?
C12 C11 H11 108.1 . . ?
O1 C1 N1 122.38(15) . . ?
O1 C1 C2 124.72(16) . . ?
N1 C1 C2 112.78(13) . . ?
N3 C3 C2 111.21(14) . . ?
N3 C3 C4 121.62(15) . . ?
C2 C3 C4 127.16(15) . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.51(15) . . ?
C8 C9 H9 119.7 . . ?
C5 C6 C7 118.98(16) . . ?
C8 C6 C5 116.93(15) . . ?
C8 C6 C7 124.09(15) . . ?
O4 C13 C12 112.42(15) . . ?
O3 C13 O4 123.52(17) . . ?
O3 C13 C12 124.04(16) . . ?
C9 C8 H8 118.8 . . ?
C6 C8 C9 122.41(15) . . ?
C6 C8 H8 118.8 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 C11 111.96(14) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.314
_oxdiff_exptl_absorpt_empirical_full_min 0.777
