# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2380936'
loop_
_audit_author_name
_audit_author_address
'Raymond J Butcher'
;Howard University, USA
United States of America
;
_audit_update_record             
;
2024-08-30 deposited with the CCDC.	2026-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O3'
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5814(4)
_cell_length_b                   11.6665(3)
_cell_length_c                   10.1069(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.112(2)
_cell_angle_gamma                90
_cell_volume                     1450.48(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7706
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.54

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4899
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31402
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.406
_diffrn_reflns_theta_max         30.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4452
_reflns_number_gt                3505
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_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)+(0.0532P)²+0.3804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4452
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O1 O 0.62963(7) 0.42951(8) 0.15718(8) 0.02262(19) Uani 1 1 d . . . . .
H1O H 0.6840(16) 0.3793(17) 0.205(2) 0.051(5) Uiso 1 1 d . . . . .
O2 O 0.87177(6) 0.22256(7) 0.20168(8) 0.01958(18) Uani 1 1 d . . . . .
O3 O 0.97854(6) 0.16308(7) 0.40140(8) 0.01750(17) Uani 1 1 d . . . . .
N1 N 0.72572(7) 0.29493(8) 0.34095(9) 0.01546(19) Uani 1 1 d . . . . .
N2 N 0.81913(7) 0.23912(8) 0.40346(9) 0.01660(19) Uani 1 1 d . . . . .
H2N H 0.8370(11) 0.2340(12) 0.4926(15) 0.020(3) Uiso 1 1 d . . . . .
C1 C 0.54767(9) 0.43150(9) 0.22535(11) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.45703(9) 0.49982(10) 0.16812(12) 0.0223(2) Uani 1 1 d . . . . .
H2A H 0.456161 0.540731 0.086628 0.027 Uiso 1 1 calc R U . . .
C3 C 0.37099(9) 0.50704(10) 0.22966(12) 0.0212(2) Uani 1 1 d . . . . .
H3A H 0.310436 0.553287 0.190308 0.025 Uiso 1 1 calc R U . . .
C4 C 0.36968(8) 0.44716(9) 0.35109(11) 0.0171(2) Uani 1 1 d . . . . .
C5 C 0.28099(9) 0.45764(10) 0.41615(12) 0.0204(2) Uani 1 1 d . . . . .
H5A H 0.221555 0.505719 0.377772 0.024 Uiso 1 1 calc R U . . .
C6 C 0.27933(9) 0.39996(10) 0.53297(13) 0.0228(2) Uani 1 1 d . . . . .
H6A H 0.219456 0.408241 0.575931 0.027 Uiso 1 1 calc R U . . .
C7 C 0.36691(9) 0.32807(10) 0.58949(13) 0.0233(2) Uani 1 1 d . . . . .
H7A H 0.365267 0.286712 0.670010 0.028 Uiso 1 1 calc R U . . .
C8 C 0.45479(9) 0.31702(10) 0.52950(12) 0.0194(2) Uani 1 1 d . . . . .
H8A H 0.513120 0.268112 0.569380 0.023 Uiso 1 1 calc R U . . .
C9 C 0.46003(8) 0.37712(9) 0.40947(10) 0.0151(2) Uani 1 1 d . . . . .
C10 C 0.55149(8) 0.37070(9) 0.34488(10) 0.0149(2) Uani 1 1 d . . . . .
C11 C 0.64898(8) 0.30721(9) 0.40662(11) 0.0152(2) Uani 1 1 d . . . . .
H11A H 0.655952 0.275164 0.494434 0.018 Uiso 1 1 calc R U . . .
C12 C 0.89011(8) 0.20975(9) 0.32378(10) 0.0148(2) Uani 1 1 d . . . . .
C13 C 1.06988(8) 0.12244(9) 0.34125(11) 0.0171(2) Uani 1 1 d . . . . .
C14 C 1.03271(10) 0.02193(10) 0.24784(14) 0.0253(3) Uani 1 1 d . . . . .
H14A H 0.998260 -0.035634 0.295656 0.038 Uiso 1 1 calc R U . . .
H14B H 1.095569 -0.012166 0.219531 0.038 Uiso 1 1 calc R U . . .
H14C H 0.980295 0.048639 0.167957 0.038 Uiso 1 1 calc R U . . .
C15 C 1.11332(9) 0.22145(10) 0.27050(12) 0.0216(2) Uani 1 1 d . . . . .
H15A H 1.064173 0.235920 0.183207 0.032 Uiso 1 1 calc R U . . .
H15B H 1.185698 0.201978 0.255679 0.032 Uiso 1 1 calc R U . . .
H15C H 1.118128 0.290305 0.326985 0.032 Uiso 1 1 calc R U . . .
C16 C 1.15273(9) 0.08452(11) 0.46524(12) 0.0239(2) Uani 1 1 d . . . . .
H16A H 1.121081 0.024405 0.512680 0.036 Uiso 1 1 calc R U . . .
H16B H 1.173207 0.150085 0.525833 0.036 Uiso 1 1 calc R U . . .
H16C H 1.217385 0.054579 0.437237 0.036 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
O1 C1 1.3552(13) . ?
O1 H1O 0.95(2) . ?
O2 C12 1.2161(13) . ?
O3 C12 1.3354(12) . ?
O3 C13 1.4859(12) . ?
N1 C11 1.2893(13) . ?
N1 N2 1.3757(12) . ?
N2 C12 1.3658(13) . ?
N2 H2N 0.883(15) . ?
C1 C10 1.3930(15) . ?
C1 C2 1.4120(15) . ?
C2 C3 1.3595(16) . ?
C2 H2A 0.9500 . ?
C3 C4 1.4152(16) . ?
C3 H3A 0.9500 . ?
C4 C5 1.4144(15) . ?
C4 C9 1.4235(14) . ?
C5 C6 1.3629(17) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4071(17) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3740(15) . ?
C7 H7A 0.9500 . ?
C8 C9 1.4147(15) . ?
C8 H8A 0.9500 . ?
C9 C10 1.4392(14) . ?
C10 C11 1.4564(14) . ?
C11 H11A 0.9500 . ?
C13 C14 1.5165(16) . ?
C13 C16 1.5180(16) . ?
C13 C15 1.5193(15) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C1 O1 H1O 107.2(11) . . ?
C12 O3 C13 120.68(8) . . ?
C11 N1 N2 118.43(9) . . ?
C12 N2 N1 116.69(9) . . ?
C12 N2 H2N 121.8(9) . . ?
N1 N2 H2N 120.7(9) . . ?
O1 C1 C10 122.73(9) . . ?
O1 C1 C2 115.89(10) . . ?
C10 C1 C2 121.37(10) . . ?
C3 C2 C1 119.98(11) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 121.42(10) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 120.95(10) . . ?
C5 C4 C9 119.74(10) . . ?
C3 C4 C9 119.29(10) . . ?
C6 C5 C4 121.14(10) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C7 119.53(10) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C8 C7 C6 120.72(11) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C7 C8 C9 121.23(10) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C8 C9 C4 117.59(9) . . ?
C8 C9 C10 123.28(9) . . ?
C4 C9 C10 119.13(10) . . ?
C1 C10 C9 118.78(9) . . ?
C1 C10 C11 120.21(9) . . ?
C9 C10 C11 120.92(9) . . ?
N1 C11 C10 119.36(9) . . ?
N1 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
O2 C12 O3 127.12(9) . . ?
O2 C12 N2 124.00(10) . . ?
O3 C12 N2 108.85(9) . . ?
O3 C13 C14 109.73(8) . . ?
O3 C13 C16 102.20(8) . . ?
C14 C13 C16 110.93(10) . . ?
O3 C13 C15 109.60(8) . . ?
C14 C13 C15 112.90(10) . . ?
C16 C13 C15 110.95(9) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C11 N1 N2 C12 168.74(9) . . . . ?
O1 C1 C2 C3 -179.94(10) . . . . ?
C10 C1 C2 C3 -0.15(18) . . . . ?
C1 C2 C3 C4 -0.03(18) . . . . ?
C2 C3 C4 C5 178.34(11) . . . . ?
C2 C3 C4 C9 -0.51(17) . . . . ?
C3 C4 C5 C6 179.88(11) . . . . ?
C9 C4 C5 C6 -1.27(16) . . . . ?
C4 C5 C6 C7 -0.45(17) . . . . ?
C5 C6 C7 C8 1.15(18) . . . . ?
C6 C7 C8 C9 -0.09(18) . . . . ?
C7 C8 C9 C4 -1.60(16) . . . . ?
C7 C8 C9 C10 178.32(10) . . . . ?
C5 C4 C9 C8 2.26(15) . . . . ?
C3 C4 C9 C8 -178.88(10) . . . . ?
C5 C4 C9 C10 -177.66(9) . . . . ?
C3 C4 C9 C10 1.20(15) . . . . ?
O1 C1 C10 C9 -179.38(10) . . . . ?
C2 C1 C10 C9 0.84(16) . . . . ?
O1 C1 C10 C11 3.99(16) . . . . ?
C2 C1 C10 C11 -175.79(10) . . . . ?
C8 C9 C10 C1 178.72(10) . . . . ?
C4 C9 C10 C1 -1.36(15) . . . . ?
C8 C9 C10 C11 -4.67(16) . . . . ?
C4 C9 C10 C11 175.24(9) . . . . ?
N2 N1 C11 C10 177.14(9) . . . . ?
C1 C10 C11 N1 -9.29(15) . . . . ?
C9 C10 C11 N1 174.16(10) . . . . ?
C13 O3 C12 O2 1.61(16) . . . . ?
C13 O3 C12 N2 179.79(8) . . . . ?
N1 N2 C12 O2 -5.50(16) . . . . ?
N1 N2 C12 O3 176.24(8) . . . . ?
C12 O3 C13 C14 -65.73(12) . . . . ?
C12 O3 C13 C16 176.51(9) . . . . ?
C12 O3 C13 C15 58.78(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N1 0.95(2) 1.68(2) 2.5366(12) 147.3(17) . yes
N2 H2N O2 0.883(15) 2.128(15) 2.9809(12) 162.2(13) 4_566 yes
C2 H2A O1 0.95 2.50 3.3427(14) 148.1 3_665 yes
C14 H14C O2 0.98 2.51 3.0659(14) 115.9 . yes
C15 H15A O2 0.98 2.47 2.9720(14) 111.4 . yes

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.062

