# Supplementary Information (SI) for RSC Advances.
# 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_d113
_database_code_depnum_ccdc_archive 'CCDC 2337812'
loop_
_audit_author_name
_audit_author_address
'Hitendra M. Patel'
;Department of Chemistry,Sardar Patel University
India
;
_audit_update_record             
;
2024-03-05 deposited with the CCDC.	2025-04-29 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         ?
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34

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                   10.3767(5)
_cell_length_b                   20.8762(10)
_cell_length_c                   8.8540(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.4574(19)
_cell_angle_gamma                90
_cell_volume                     1759.50(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2425
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      21.73

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            12645
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3111
_reflns_number_gt                2010
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0406P)²+0.6161P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3111
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.4533(2) 0.15230(11) 0.5354(2) 0.0502(6) Uani 1 1 d . . . . .
H1 H 0.3790 0.1361 0.5572 0.060 Uiso 1 1 calc R U . . .
C2 C 0.5497(3) 0.10998(12) 0.5140(3) 0.0621(7) Uani 1 1 d . . . . .
H2 H 0.5411 0.0659 0.5226 0.075 Uiso 1 1 calc R U . . .
C3 C 0.6576(3) 0.13566(14) 0.4800(3) 0.0643(7) Uani 1 1 d . . . . .
C4 C 0.6740(3) 0.20043(14) 0.4717(3) 0.0655(7) Uani 1 1 d . . . . .
H4 H 0.7482 0.2164 0.4493 0.079 Uiso 1 1 calc R U . . .
C5 C 0.5816(2) 0.24176(12) 0.4963(2) 0.0490(6) Uani 1 1 d . . . . .
C6 C 0.4671(2) 0.21683(10) 0.5245(2) 0.0400(5) Uani 1 1 d . . . . .
C7 C 0.2895(2) 0.29854(9) 0.4218(2) 0.0361(5) Uani 1 1 d . . . . .
C8 C 0.1854(2) 0.34389(9) 0.4493(2) 0.0386(5) Uani 1 1 d . . . . .
C9 C 0.1947(2) 0.34543(10) 0.6275(2) 0.0462(5) Uani 1 1 d . . . . .
H9A H 0.1616 0.3049 0.6523 0.055 Uiso 1 1 calc R U . . .
H9B H 0.2921 0.3506 0.7028 0.055 Uiso 1 1 calc R U . . .
C10 C 0.1112(3) 0.39755(12) 0.6526(3) 0.0570(6) Uani 1 1 d . . . . .
C11 C 0.0441(3) 0.43944(14) 0.6686(3) 0.0819(9) Uani 1 1 d . . . . .
H11 H -0.0097 0.4730 0.6814 0.098 Uiso 1 1 calc R U . . .
C12 C 0.0364(2) 0.32432(12) 0.3293(3) 0.0526(6) Uani 1 1 d . . . . .
H12A H -0.0318 0.3525 0.3446 0.063 Uiso 1 1 calc R U . . .
H12B H 0.0284 0.3294 0.2170 0.063 Uiso 1 1 calc R U . . .
C13 C 0.0050(2) 0.25846(14) 0.3548(3) 0.0550(6) Uani 1 1 d . . . . .
C14 C -0.0135(3) 0.20518(16) 0.3780(3) 0.0744(8) Uani 1 1 d . . . . .
H14 H -0.0283 0.1625 0.3966 0.089 Uiso 1 1 calc R U . . .
C15 C 0.2206(3) 0.41030(12) 0.4030(3) 0.0586(6) Uani 1 1 d . . . . .
C16 C 0.3641(3) 0.43587(14) 0.5028(4) 0.1016(11) Uani 1 1 d . . . . .
H16A H 0.3812 0.4730 0.4495 0.152 Uiso 1 1 calc R U . . .
H16B H 0.4329 0.4036 0.5126 0.152 Uiso 1 1 calc R U . . .
H16C H 0.3702 0.4474 0.6104 0.152 Uiso 1 1 calc R U . . .
C17 C 0.7077(3) 0.33299(15) 0.4671(4) 0.0851(9) Uani 1 1 d . . . . .
H17A H 0.7950 0.3171 0.5470 0.128 Uiso 1 1 calc R U . . .
H17B H 0.7055 0.3788 0.4752 0.128 Uiso 1 1 calc R U . . .
H17C H 0.6991 0.3213 0.3587 0.128 Uiso 1 1 calc R U . . .
C18 C 0.7507(4) 0.03301(17) 0.4629(5) 0.1308(15) Uani 1 1 d . . . . .
H18A H 0.7675 0.0210 0.5738 0.196 Uiso 1 1 calc R U . . .
H18B H 0.8207 0.0138 0.4319 0.196 Uiso 1 1 calc R U . . .
H18C H 0.6593 0.0185 0.3899 0.196 Uiso 1 1 calc R U . . .
N1 N 0.36741(16) 0.25946(8) 0.54316(18) 0.0397(4) Uani 1 1 d . . . . .
H1A H 0.3571 0.2601 0.6348 0.048 Uiso 1 1 calc R U . . .
O1 O 0.7576(2) 0.09915(11) 0.4527(3) 0.1019(7) Uani 1 1 d . . . . .
O2 O 0.59360(16) 0.30594(8) 0.4976(2) 0.0668(5) Uani 1 1 d . . . . .
O3 O 0.29752(14) 0.30051(7) 0.28700(15) 0.0459(4) Uani 1 1 d . . . . .
O4 O 0.1358(2) 0.44049(9) 0.2920(2) 0.0839(6) 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 C6 1.362(3) . ?
C1 C2 1.402(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 O1 1.384(3) . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 O2 1.345(3) . ?
C5 C6 1.407(3) . ?
C6 N1 1.423(2) . ?
C7 O3 1.230(2) . ?
C7 N1 1.335(2) . ?
C7 C8 1.527(3) . ?
C8 C15 1.531(3) . ?
C8 C9 1.542(2) . ?
C8 C12 1.542(3) . ?
C9 C10 1.462(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.162(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.451(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.161(3) . ?
C14 H14 0.9300 . ?
C15 O4 1.203(3) . ?
C15 C16 1.495(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O2 1.431(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O1 1.387(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1A 0.8600 . ?

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
C6 C1 C2 120.9(2) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 O1 114.6(2) . . ?
C2 C3 O1 123.7(3) . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
O2 C5 C4 124.1(2) . . ?
O2 C5 C6 116.66(18) . . ?
C4 C5 C6 119.3(2) . . ?
C1 C6 C5 119.88(19) . . ?
C1 C6 N1 120.56(18) . . ?
C5 C6 N1 119.55(19) . . ?
O3 C7 N1 123.25(17) . . ?
O3 C7 C8 117.36(17) . . ?
N1 C7 C8 119.39(15) . . ?
C7 C8 C15 105.03(16) . . ?
C7 C8 C9 114.56(15) . . ?
C15 C8 C9 109.33(17) . . ?
C7 C8 C12 107.73(16) . . ?
C15 C8 C12 109.63(18) . . ?
C9 C8 C12 110.37(16) . . ?
C10 C9 C8 111.82(17) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 178.3(2) . . ?
C10 C11 H11 180.0 . . ?
C13 C12 C8 111.65(18) . . ?
C13 C12 H12A 109.3 . . ?
C8 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C8 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 176.8(3) . . ?
C13 C14 H14 180.0 . . ?
O4 C15 C16 121.9(3) . . ?
O4 C15 C8 121.2(2) . . ?
C16 C15 C8 116.9(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 N1 C6 121.61(15) . . ?
C7 N1 H1A 119.2 . . ?
C6 N1 H1A 119.2 . . ?
C3 O1 C18 118.4(3) . . ?
C5 O2 C17 118.19(19) . . ?

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
C6 C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 C4 1.9(4) . . . . ?
C1 C2 C3 O1 -178.5(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
O1 C3 C4 C5 180.0(2) . . . . ?
C3 C4 C5 O2 176.9(2) . . . . ?
C3 C4 C5 C6 -2.2(3) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
C2 C1 C6 N1 178.79(18) . . . . ?
O2 C5 C6 C1 -175.86(18) . . . . ?
C4 C5 C6 C1 3.3(3) . . . . ?
O2 C5 C6 N1 3.5(3) . . . . ?
C4 C5 C6 N1 -177.33(19) . . . . ?
O3 C7 C8 C15 -52.2(2) . . . . ?
N1 C7 C8 C15 127.25(19) . . . . ?
O3 C7 C8 C9 -172.21(18) . . . . ?
N1 C7 C8 C9 7.3(3) . . . . ?
O3 C7 C8 C12 64.6(2) . . . . ?
N1 C7 C8 C12 -115.94(19) . . . . ?
C7 C8 C9 C10 169.73(19) . . . . ?
C15 C8 C9 C10 52.2(2) . . . . ?
C12 C8 C9 C10 -68.5(2) . . . . ?
C7 C8 C12 C13 58.8(2) . . . . ?
C15 C8 C12 C13 172.61(16) . . . . ?
C9 C8 C12 C13 -66.9(2) . . . . ?
C7 C8 C15 O4 118.5(2) . . . . ?
C9 C8 C15 O4 -118.1(2) . . . . ?
C12 C8 C15 O4 3.0(3) . . . . ?
C7 C8 C15 C16 -62.1(2) . . . . ?
C9 C8 C15 C16 61.3(3) . . . . ?
C12 C8 C15 C16 -177.6(2) . . . . ?
O3 C7 N1 C6 0.2(3) . . . . ?
C8 C7 N1 C6 -179.25(17) . . . . ?
C1 C6 N1 C7 -118.3(2) . . . . ?
C5 C6 N1 C7 62.4(2) . . . . ?
C4 C3 O1 C18 178.5(3) . . . . ?
C2 C3 O1 C18 -1.1(4) . . . . ?
C4 C5 O2 C17 1.7(3) . . . . ?
C6 C5 O2 C17 -179.17(19) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.033

