# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2501597'
loop_
_audit_author_name
_audit_author_address
'Che-Chien Chang'
;Fu Jen Catholic University
Taiwan
;
_audit_update_record             
;
2025-11-10 deposited with the CCDC.	2026-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 N3 O3'
_chemical_formula_sum            'C13 H17 N3 O3'
_chemical_formula_weight         263.29

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.8928(6)
_cell_length_b                   13.3792(15)
_cell_length_c                   16.7377(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1319.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3182
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      23.02

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.790
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8375
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_full        25.034
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2319
_reflns_number_gt                1948
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0604P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 671 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2319
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C -0.1136(5) 0.4472(2) 0.51064(19) 0.0321(8) Uani 1 1 d . . . . .
C2 C -0.3697(5) 0.4526(3) 0.5105(2) 0.0398(9) Uani 1 1 d . . . . .
H2A H -0.4298 0.4106 0.5536 0.060 Uiso 1 1 calc R U . . .
H2B H -0.4276 0.4286 0.4591 0.060 Uiso 1 1 calc R U . . .
H2C H -0.4178 0.5219 0.5188 0.060 Uiso 1 1 calc R U . . .
C3 C -0.0263(7) 0.3444(3) 0.4880(2) 0.0500(10) Uani 1 1 d . . . . .
H3A H -0.0751 0.2956 0.5281 0.075 Uiso 1 1 calc R U . . .
H3B H 0.1398 0.3457 0.4855 0.075 Uiso 1 1 calc R U . . .
H3C H -0.0873 0.3255 0.4356 0.075 Uiso 1 1 calc R U . . .
C4 C -0.0185(6) 0.4808(3) 0.59047(19) 0.0463(9) Uani 1 1 d . . . . .
H4A H -0.0753 0.4368 0.6328 0.069 Uiso 1 1 calc R U . . .
H4B H -0.0665 0.5496 0.6012 0.069 Uiso 1 1 calc R U . . .
H4C H 0.1476 0.4776 0.5890 0.069 Uiso 1 1 calc R U . . .
C5 C -0.0562(5) 0.5221(2) 0.37709(19) 0.0313(7) Uani 1 1 d . . . . .
C6 C 0.2854(5) 0.6327(2) 0.38216(17) 0.0304(7) Uani 1 1 d . . . . .
H6A H 0.3917 0.5807 0.4015 0.036 Uiso 1 1 calc R U . . .
H6B H 0.2339 0.6735 0.4281 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3945(5) 0.6969(2) 0.31910(17) 0.0275(7) Uani 1 1 d . . . . .
C8 C 0.2723(6) 0.6904(3) 0.25111(19) 0.0346(8) Uani 1 1 d . . . . .
H8 H 0.3070 0.7250 0.2031 0.042 Uiso 1 1 calc R U . . .
C9 C 0.0798(5) 0.6229(2) 0.26121(18) 0.0317(8) Uani 1 1 d . . . . .
C10 C 0.5944(5) 0.7515(2) 0.34124(17) 0.0276(7) Uani 1 1 d . . . . .
C11 C 0.7056(5) 0.7525(2) 0.41335(18) 0.0319(7) Uani 1 1 d . . . . .
H11 H 0.6590 0.7155 0.4590 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8935(5) 0.8492(2) 0.3377(2) 0.0353(8) Uani 1 1 d . . . . .
H12 H 1.0052 0.8943 0.3184 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6786(7) 0.8401(3) 0.2094(2) 0.0491(10) Uani 1 1 d . . . . .
H13A H 0.7982 0.8849 0.1902 0.074 Uiso 1 1 calc R U . . .
H13B H 0.5310 0.8732 0.2044 0.074 Uiso 1 1 calc R U . . .
H13C H 0.6787 0.7787 0.1774 0.074 Uiso 1 1 calc R U . . .
N1 N 0.0927(4) 0.58783(19) 0.34022(15) 0.0293(6) Uani 1 1 d . . . . .
N2 N 0.8926(4) 0.8135(2) 0.41117(16) 0.0353(7) Uani 1 1 d . . . . .
N3 N 0.7198(4) 0.8153(2) 0.29279(15) 0.0302(6) Uani 1 1 d . . . . .
O1 O -0.0122(4) 0.52125(16) 0.45504(12) 0.0352(6) Uani 1 1 d . . . . .
O2 O -0.1973(4) 0.47304(19) 0.34275(13) 0.0436(6) Uani 1 1 d . . . . .
O3 O -0.0643(4) 0.6001(2) 0.21246(13) 0.0494(7) 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
C1 O1 1.484(4) . ?
C1 C2 1.511(4) . ?
C1 C4 1.517(4) . ?
C1 C3 1.517(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 O2 1.205(4) . ?
C5 O1 1.330(4) . ?
C5 N1 1.387(4) . ?
C6 N1 1.464(4) . ?
C6 C7 1.505(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.349(4) . ?
C7 C10 1.434(4) . ?
C8 C9 1.460(5) . ?
C8 H8 0.9500 . ?
C9 O3 1.216(4) . ?
C9 N1 1.405(4) . ?
C10 C11 1.374(4) . ?
C10 N3 1.390(4) . ?
C11 N2 1.372(4) . ?
C11 H11 0.9500 . ?
C12 N2 1.320(4) . ?
C12 N3 1.348(4) . ?
C12 H12 0.9500 . ?
C13 N3 1.455(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
O1 C1 C2 111.7(3) . . ?
O1 C1 C4 101.9(2) . . ?
C2 C1 C4 110.9(3) . . ?
O1 C1 C3 108.2(3) . . ?
C2 C1 C3 112.4(3) . . ?
C4 C1 C3 111.3(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 O1 126.7(3) . . ?
O2 C5 N1 124.7(3) . . ?
O1 C5 N1 108.5(3) . . ?
N1 C6 C7 103.2(2) . . ?
N1 C6 H6A 111.1 . . ?
C7 C6 H6A 111.1 . . ?
N1 C6 H6B 111.1 . . ?
C7 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C10 133.6(3) . . ?
C8 C7 C6 109.1(3) . . ?
C10 C7 C6 117.4(3) . . ?
C7 C8 C9 110.9(3) . . ?
C7 C8 H8 124.5 . . ?
C9 C8 H8 124.5 . . ?
O3 C9 N1 125.8(3) . . ?
O3 C9 C8 128.3(3) . . ?
N1 C9 C8 105.9(3) . . ?
C11 C10 N3 104.6(3) . . ?
C11 C10 C7 128.6(3) . . ?
N3 C10 C7 126.8(3) . . ?
N2 C11 C10 111.4(3) . . ?
N2 C11 H11 124.3 . . ?
C10 C11 H11 124.3 . . ?
N2 C12 N3 113.2(3) . . ?
N2 C12 H12 123.4 . . ?
N3 C12 H12 123.4 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 N1 C9 126.6(3) . . ?
C5 N1 C6 122.5(2) . . ?
C9 N1 C6 110.9(2) . . ?
C12 N2 C11 104.1(3) . . ?
C12 N3 C10 106.6(3) . . ?
C12 N3 C13 125.8(3) . . ?
C10 N3 C13 127.6(3) . . ?
C5 O1 C1 122.8(2) . . ?

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039

