# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_Compound_1c
_database_code_depnum_ccdc_archive 'CCDC 2454559'
loop_
_audit_author_name
_audit_author_address
'Rishu Kumar Pandey'
;Indian Institute of Science Education and Research, Pune
India
;
_audit_update_record             
;
2025-05-27 deposited with the CCDC.	2026-02-02 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            'C23 H26 N4 O4'
_chemical_formula_weight         422.48

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                   12.2023(11)
_cell_length_b                   10.9757(10)
_cell_length_c                   16.4527(13)
_cell_angle_alpha                90
_cell_angle_beta                 105.485(2)
_cell_angle_gamma                90
_cell_volume                     2123.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.68

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.4452
_shelx_estimated_absorpt_T_max   0.7452
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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            53321
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.1319
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_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             3749
_reflns_number_gt                2930
_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       ?
_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)+(0.0650P)²+0.9972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3749
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
O4 O 0.74768(13) 0.61595(14) 0.66185(9) 0.0291(4) Uani 1 1 d G . . . .
H4A H 0.7340 0.5692 0.6191 0.044 Uiso 1 1 d G U . . .
H4B H 0.8062 0.5854 0.6958 0.044 Uiso 1 1 d G U . . .
N1 N -0.05106(17) -0.01462(18) 0.26947(12) 0.0330(5) Uani 1 1 d . . . . .
C1 C 0.00821(19) 0.0686(2) 0.23995(14) 0.0291(5) Uani 1 1 d . . . . .
H1 H -0.0225 0.0974 0.1840 0.035 Uiso 1 1 calc R U . . .
O1 O 0.30439(14) 0.01085(15) 0.53034(10) 0.0358(4) Uani 1 1 d . . . . .
N2 N 0.26293(15) 0.12482(16) 0.41094(10) 0.0229(4) Uani 1 1 d . . . . .
H2A H 0.2879 0.1858 0.3861 0.027 Uiso 1 1 calc R U . . .
C2 C 0.11087(18) 0.1152(2) 0.28524(13) 0.0255(5) Uani 1 1 d . . . . .
H2 H 0.1487 0.1748 0.2608 0.031 Uiso 1 1 calc R U . . .
O2 O 0.68382(12) 0.49505(13) 0.50470(8) 0.0219(4) Uani 1 1 d . . . . .
N3 N 0.54613(14) 0.44598(15) 0.38596(9) 0.0158(4) Uani 1 1 d . . . . .
H3 H 0.4983 0.3878 0.3629 0.019 Uiso 1 1 calc R U . . .
C3 C 0.15904(17) 0.07460(19) 0.36718(13) 0.0214(5) Uani 1 1 d . . . . .
O3 O 0.67863(12) 0.13668(13) 0.70275(9) 0.0266(4) Uani 1 1 d . . . . .
N4 N 0.54534(15) 0.73976(15) 0.22206(10) 0.0193(4) Uani 1 1 d . . . . .
C4 C 0.0989(2) -0.0116(2) 0.39975(15) 0.0315(6) Uani 1 1 d . . . . .
H4 H 0.1275 -0.0421 0.4554 0.038 Uiso 1 1 calc R U . . .
C5 C -0.0042(2) -0.0517(2) 0.34835(15) 0.0366(6) Uani 1 1 d . . . . .
H5 H -0.0449 -0.1104 0.3712 0.044 Uiso 1 1 calc R U . . .
C6 C 0.33055(17) 0.09054(19) 0.48789(13) 0.0198(5) Uani 1 1 d . . . . .
C7 C 0.44159(17) 0.15795(18) 0.51769(12) 0.0160(4) Uani 1 1 d . . . . .
C8 C 0.51488(17) 0.11908(19) 0.59225(12) 0.0188(5) Uani 1 1 d . . . . .
H8 H 0.4956 0.0500 0.6203 0.023 Uiso 1 1 calc R U . . .
C9 C 0.61681(17) 0.17992(18) 0.62690(12) 0.0181(5) Uani 1 1 d . . . . .
C10 C 0.64708(17) 0.27803(18) 0.58442(12) 0.0184(5) Uani 1 1 d . . . . .
H10 H 0.7175 0.3185 0.6069 0.022 Uiso 1 1 calc R U . . .
C11 C 0.57390(16) 0.31691(18) 0.50873(11) 0.0147(4) Uani 1 1 d . . . . .
C12 C 0.47050(17) 0.25768(18) 0.47604(12) 0.0163(4) Uani 1 1 d . . . . .
H12 H 0.4197 0.2857 0.4251 0.020 Uiso 1 1 calc R U . . .
C13 C 0.60745(17) 0.42710(17) 0.46710(12) 0.0159(4) Uani 1 1 d . . . . .
C14 C 0.54998(17) 0.54681(18) 0.33476(12) 0.0146(4) Uani 1 1 d . . . . .
C15 C 0.46208(17) 0.55847(18) 0.26096(12) 0.0171(4) Uani 1 1 d . . . . .
H15 H 0.4017 0.5010 0.2477 0.020 Uiso 1 1 calc R U . . .
C16 C 0.46408(18) 0.65434(19) 0.20769(12) 0.0196(5) Uani 1 1 d . . . . .
H16 H 0.4040 0.6604 0.1574 0.024 Uiso 1 1 calc R U . . .
C17 C 0.62809(18) 0.72755(19) 0.29406(12) 0.0208(5) Uani 1 1 d . . . . .
H17 H 0.6861 0.7878 0.3065 0.025 Uiso 1 1 calc R U . . .
C18 C 0.63530(17) 0.63445(18) 0.35130(12) 0.0172(5) Uani 1 1 d . . . . .
H18 H 0.6969 0.6302 0.4007 0.021 Uiso 1 1 calc R U . . .
C19 C 0.77741(18) 0.2036(2) 0.74745(13) 0.0242(5) Uani 1 1 d . . . . .
H19A H 0.7603 0.2918 0.7465 0.029 Uiso 1 1 calc R U . . .
H19B H 0.8405 0.1907 0.7210 0.029 Uiso 1 1 calc R U . . .
C20 C 0.80996(18) 0.1570(2) 0.83698(13) 0.0243(5) Uani 1 1 d . . . . .
H20A H 0.8130 0.0669 0.8363 0.029 Uiso 1 1 calc R U . . .
H20B H 0.7509 0.1812 0.8650 0.029 Uiso 1 1 calc R U . . .
C21 C 0.92412(19) 0.2061(2) 0.88704(13) 0.0274(5) Uani 1 1 d . . . . .
H21A H 0.9237 0.2959 0.8817 0.033 Uiso 1 1 calc R U . . .
H21B H 0.9840 0.1741 0.8624 0.033 Uiso 1 1 calc R U . . .
C22 C 0.95367(19) 0.1726(2) 0.97999(13) 0.0279(5) Uani 1 1 d . . . . .
H22A H 0.9060 0.2211 1.0081 0.033 Uiso 1 1 calc R U . . .
H22B H 0.9361 0.0854 0.9856 0.033 Uiso 1 1 calc R U . . .
C23 C 1.0783(2) 0.1954(3) 1.02358(14) 0.0362(6) Uani 1 1 d . . . . .
H23A H 1.1257 0.1441 0.9979 0.054 Uiso 1 1 calc R U . . .
H23B H 1.0933 0.1755 1.0836 0.054 Uiso 1 1 calc R U . . .
H23C H 1.0963 0.2814 1.0173 0.054 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
O4 H4A 0.8500 . ?
O4 H4B 0.8499 . ?
N1 C1 1.334(3) . ?
N1 C5 1.334(3) . ?
C1 C2 1.374(3) . ?
C1 H1 0.9500 . ?
O1 C6 1.214(2) . ?
N2 C6 1.367(3) . ?
N2 C3 1.393(3) . ?
N2 H2A 0.8800 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
O2 C13 1.225(2) . ?
N3 C13 1.361(2) . ?
N3 C14 1.399(2) . ?
N3 H3 0.8800 . ?
C3 C4 1.389(3) . ?
O3 C9 1.360(2) . ?
O3 C19 1.435(2) . ?
N4 C16 1.339(3) . ?
N4 C17 1.342(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.506(3) . ?
C7 C8 1.379(3) . ?
C7 C12 1.386(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 C13 1.500(3) . ?
C12 H12 0.9500 . ?
C14 C18 1.390(3) . ?
C14 C15 1.395(3) . ?
C15 C16 1.374(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.509(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.515(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.520(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.519(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
H4A O4 H4B 104.5 . . ?
C1 N1 C5 115.5(2) . . ?
N1 C1 C2 124.2(2) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C6 N2 C3 127.64(18) . . ?
C6 N2 H2A 116.2 . . ?
C3 N2 H2A 116.2 . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C13 N3 C14 127.81(17) . . ?
C13 N3 H3 116.1 . . ?
C14 N3 H3 116.1 . . ?
C4 C3 C2 117.48(19) . . ?
C4 C3 N2 124.84(19) . . ?
C2 C3 N2 117.66(19) . . ?
C9 O3 C19 118.42(16) . . ?
C16 N4 C17 115.66(17) . . ?
C5 C4 C3 117.9(2) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 125.4(2) . . ?
N1 C5 H5 117.3 . . ?
C4 C5 H5 117.3 . . ?
O1 C6 N2 123.02(19) . . ?
O1 C6 C7 121.23(18) . . ?
N2 C6 C7 115.75(18) . . ?
C8 C7 C12 119.60(19) . . ?
C8 C7 C6 116.81(18) . . ?
C12 C7 C6 123.54(18) . . ?
C7 C8 C9 120.80(19) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
O3 C9 C10 125.21(18) . . ?
O3 C9 C8 115.10(18) . . ?
C10 C9 C8 119.68(18) . . ?
C9 C10 C11 119.70(19) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.06(18) . . ?
C10 C11 C13 117.89(18) . . ?
C12 C11 C13 121.97(17) . . ?
C7 C12 C11 120.09(18) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
O2 C13 N3 123.22(18) . . ?
O2 C13 C11 121.61(17) . . ?
N3 C13 C11 115.16(17) . . ?
C18 C14 C15 117.94(18) . . ?
C18 C14 N3 124.99(17) . . ?
C15 C14 N3 117.07(17) . . ?
C16 C15 C14 119.02(19) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
N4 C16 C15 124.20(19) . . ?
N4 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
N4 C17 C18 124.99(19) . . ?
N4 C17 H17 117.5 . . ?
C18 C17 H17 117.5 . . ?
C17 C18 C14 118.18(19) . . ?
C17 C18 H18 120.9 . . ?
C14 C18 H18 120.9 . . ?
O3 C19 C20 107.03(17) . . ?
O3 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
O3 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
C19 C20 C21 111.97(18) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 C22 113.42(19) . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 111.96(19) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C5 N1 C1 C2 0.2(4) . . . . ?
N1 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 N2 -179.7(2) . . . . ?
C6 N2 C3 C4 8.2(4) . . . . ?
C6 N2 C3 C2 -173.0(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
N2 C3 C4 C5 179.3(2) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
C3 C4 C5 N1 0.2(4) . . . . ?
C3 N2 C6 O1 -2.7(4) . . . . ?
C3 N2 C6 C7 177.09(19) . . . . ?
O1 C6 C7 C8 4.4(3) . . . . ?
N2 C6 C7 C8 -175.45(18) . . . . ?
O1 C6 C7 C12 -173.2(2) . . . . ?
N2 C6 C7 C12 7.0(3) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C6 C7 C8 C9 -176.64(18) . . . . ?
C19 O3 C9 C10 6.6(3) . . . . ?
C19 O3 C9 C8 -172.37(18) . . . . ?
C7 C8 C9 O3 176.63(18) . . . . ?
C7 C8 C9 C10 -2.4(3) . . . . ?
O3 C9 C10 C11 -177.16(19) . . . . ?
C8 C9 C10 C11 1.8(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 C13 177.07(17) . . . . ?
C8 C7 C12 C11 1.1(3) . . . . ?
C6 C7 C12 C11 178.51(18) . . . . ?
C10 C11 C12 C7 -1.7(3) . . . . ?
C13 C11 C12 C7 -178.37(17) . . . . ?
C14 N3 C13 O2 -6.4(3) . . . . ?
C14 N3 C13 C11 172.70(17) . . . . ?
C10 C11 C13 O2 -14.0(3) . . . . ?
C12 C11 C13 O2 162.81(19) . . . . ?
C10 C11 C13 N3 166.90(17) . . . . ?
C12 C11 C13 N3 -16.3(3) . . . . ?
C13 N3 C14 C18 15.1(3) . . . . ?
C13 N3 C14 C15 -166.01(19) . . . . ?
C18 C14 C15 C16 0.7(3) . . . . ?
N3 C14 C15 C16 -178.28(17) . . . . ?
C17 N4 C16 C15 -0.3(3) . . . . ?
C14 C15 C16 N4 -0.6(3) . . . . ?
C16 N4 C17 C18 1.2(3) . . . . ?
N4 C17 C18 C14 -1.1(3) . . . . ?
C15 C14 C18 C17 0.1(3) . . . . ?
N3 C14 C18 C17 178.99(18) . . . . ?
C9 O3 C19 C20 164.88(18) . . . . ?
O3 C19 C20 C21 170.79(18) . . . . ?
C19 C20 C21 C22 173.5(2) . . . . ?
C20 C21 C22 C23 166.0(2) . . . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.063

