# 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_bnh4a
_database_code_depnum_ccdc_archive 'CCDC 2409956'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam Khomeini International University
Iran
;
_audit_update_record             
;
2024-12-12 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N4 O5 Zn'
_chemical_formula_sum            'C18 H20 N4 O5 Zn'
_chemical_formula_weight         437.75

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.037(2)
_cell_length_b                   10.049(3)
_cell_length_c                   10.795(3)
_cell_angle_alpha                80.44(4)
_cell_angle_beta                 78.53(4)
_cell_angle_gamma                79.74(3)
_cell_volume                     936.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5283
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.350
_shelx_estimated_absorpt_T_min   0.642
_shelx_estimated_absorpt_T_max   0.823
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_measurement_device_type  
;
Kuma KM4 kappa-geometry diffractometer with a CCD detector
;
_diffrn_measurement_method       w/
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7344
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.878
_diffrn_reflns_theta_max         26.556
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3855
_reflns_number_gt                3579
_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       'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0927P)²+0.6169P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3855
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.003
_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
Zn Zn 0.30385(3) 0.31960(3) 0.32454(3) 0.01661(15) Uani 1 1 d . . . . .
C1 C -0.0322(3) 0.2107(3) 0.6598(3) 0.0167(6) Uani 1 1 d . . . . .
C2 C -0.0954(3) 0.1032(3) 0.6329(3) 0.0203(6) Uani 1 1 d . . . . .
H2 H -0.0704 0.0784 0.5493 0.024 Uiso 1 1 calc R U . . .
C3 C -0.1927(3) 0.0328(3) 0.7246(3) 0.0200(6) Uani 1 1 d . . . . .
H3 H -0.2345 -0.0391 0.7034 0.024 Uiso 1 1 calc R U . . .
C4 C -0.2303(3) 0.0668(3) 0.8496(3) 0.0200(6) Uani 1 1 d . . . . .
C5 C -0.1697(4) 0.1774(3) 0.8766(3) 0.0228(6) Uani 1 1 d . . . . .
H5 H -0.1966 0.2040 0.9595 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0720(3) 0.2468(3) 0.7838(3) 0.0218(6) Uani 1 1 d . . . . .
H6 H -0.0313 0.3199 0.8040 0.026 Uiso 1 1 calc R U . . .
N3 N -0.3230(3) -0.0035(3) 0.9417(3) 0.0267(6) Uani 1 1 d . . . . .
H3A H -0.358(4) 0.020(3) 1.015(4) 0.014(8) Uiso 1 1 d . . . . .
H3B H -0.367(5) -0.066(5) 0.923(4) 0.042(12) Uiso 1 1 d . . . . .
O1 O 0.1277(2) 0.2226(2) 0.45820(19) 0.0191(4) Uani 1 1 d . . . . .
C7 C 0.0784(3) 0.2725(3) 0.5592(3) 0.0170(6) Uani 1 1 d . . . . .
N1 N 0.1306(3) 0.3875(3) 0.5777(2) 0.0173(5) Uani 1 1 d . . . . .
H1 H 0.091(5) 0.421(4) 0.630(4) 0.025(11) Uiso 1 1 d . . . . .
N2 N 0.2325(3) 0.4374(2) 0.4772(2) 0.0170(5) Uani 1 1 d . . . . .
C8 C 0.2938(3) 0.5440(3) 0.4770(3) 0.0162(5) Uani 1 1 d . . . . .
C9 C 0.2653(4) 0.6263(3) 0.5851(3) 0.0206(6) Uani 1 1 d . . . . .
H9A H 0.1734 0.6939 0.5798 0.031 Uiso 1 1 calc R U . . .
H9B H 0.3530 0.6732 0.5801 0.031 Uiso 1 1 calc R U . . .
H9C H 0.2509 0.5657 0.6663 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3985(3) 0.5802(3) 0.3562(3) 0.0180(6) Uani 1 1 d . . . . .
N21 N 0.4205(3) 0.4937(3) 0.2692(2) 0.0196(5) Uani 1 1 d . . . . .
C31 C 0.5132(4) 0.5188(3) 0.1580(3) 0.0219(6) Uani 1 1 d . . . . .
H31 H 0.5296 0.4558 0.0982 0.026 Uiso 1 1 calc R U . . .
C41 C 0.5869(4) 0.6334(3) 0.1257(3) 0.0258(7) Uani 1 1 d . . . . .
H41 H 0.6502 0.6501 0.0450 0.031 Uiso 1 1 calc R U . . .
C51 C 0.5647(4) 0.7222(3) 0.2155(3) 0.0258(7) Uani 1 1 d . . . . .
H51 H 0.6133 0.8014 0.1968 0.031 Uiso 1 1 calc R U . . .
C61 C 0.4713(4) 0.6953(3) 0.3328(3) 0.0214(6) Uani 1 1 d . . . . .
H61 H 0.4574 0.7542 0.3958 0.026 Uiso 1 1 calc R U . . .
O1A O 0.2238(2) 0.2970(2) 0.17516(19) 0.0198(4) Uani 1 1 d . . . . .
C1A C 0.0876(3) 0.3594(3) 0.1718(3) 0.0193(6) Uani 1 1 d . . . . .
O2A O 0.0269(3) 0.4519(2) 0.2371(2) 0.0264(5) Uani 1 1 d . . . . .
C2A C 0.0018(4) 0.3150(4) 0.0833(4) 0.0358(8) Uani 1 1 d . . . . .
H2A1 H -0.1082 0.3402 0.1112 0.054 Uiso 1 1 calc R U . . .
H2A2 H 0.0262 0.2158 0.0847 0.054 Uiso 1 1 calc R U . . .
H2A3 H 0.0317 0.3600 -0.0037 0.054 Uiso 1 1 calc R U . . .
O1B O 0.4739(2) 0.1825(2) 0.3727(2) 0.0223(5) Uani 1 1 d . . . . .
C1B C 0.5647(3) 0.1213(3) 0.2855(3) 0.0220(6) Uani 1 1 d . . . . .
O2B O 0.5515(3) 0.1399(3) 0.1716(2) 0.0341(6) Uani 1 1 d . . . . .
C2B C 0.6944(4) 0.0210(4) 0.3311(4) 0.0325(8) Uani 1 1 d . . . . .
H2B1 H 0.7538 -0.0255 0.2601 0.049 Uiso 1 1 calc R U . . .
H2B2 H 0.6531 -0.0465 0.3997 0.049 Uiso 1 1 calc R U . . .
H2B3 H 0.7605 0.0697 0.3633 0.049 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
Zn O1A 1.954(2) . ?
Zn O1B 1.963(2) . ?
Zn N2 2.118(3) . ?
Zn N21 2.142(3) . ?
Zn O1 2.177(2) . ?
C1 C2 1.402(4) . ?
C1 C6 1.405(4) . ?
C1 C7 1.459(4) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(4) . ?
C3 H3 0.9500 . ?
C4 N3 1.355(4) . ?
C4 C5 1.416(4) . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N3 H3A 0.85(4) . ?
N3 H3B 0.87(5) . ?
O1 C7 1.244(4) . ?
C7 N1 1.380(4) . ?
N1 N2 1.365(4) . ?
N1 H1 0.71(4) . ?
N2 C8 1.290(4) . ?
C8 C11 1.484(4) . ?
C8 C9 1.496(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 N21 1.346(4) . ?
C11 C61 1.394(4) . ?
N21 C31 1.335(4) . ?
C31 C41 1.392(4) . ?
C31 H31 0.9500 . ?
C41 C51 1.386(5) . ?
C41 H41 0.9500 . ?
C51 C61 1.390(5) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
O1A C1A 1.282(4) . ?
C1A O2A 1.243(4) . ?
C1A C2A 1.508(4) . ?
C2A H2A1 0.9800 . ?
C2A H2A2 0.9800 . ?
C2A H2A3 0.9800 . ?
O1B C1B 1.282(4) . ?
C1B O2B 1.240(4) . ?
C1B C2B 1.509(4) . ?
C2B H2B1 0.9800 . ?
C2B H2B2 0.9800 . ?
C2B H2B3 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
O1A Zn O1B 116.97(9) . . ?
O1A Zn N2 136.36(9) . . ?
O1B Zn N2 105.63(9) . . ?
O1A Zn N21 106.11(9) . . ?
O1B Zn N21 99.12(9) . . ?
N2 Zn N21 74.51(10) . . ?
O1A Zn O1 93.43(9) . . ?
O1B Zn O1 94.93(9) . . ?
N2 Zn O1 73.15(9) . . ?
N21 Zn O1 147.15(9) . . ?
C2 C1 C6 118.2(3) . . ?
C2 C1 C7 117.7(3) . . ?
C6 C1 C7 124.0(3) . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
N3 C4 C3 121.0(3) . . ?
N3 C4 C5 120.7(3) . . ?
C3 C4 C5 118.3(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C4 N3 H3A 124(2) . . ?
C4 N3 H3B 120(3) . . ?
H3A N3 H3B 115(4) . . ?
C7 O1 Zn 116.30(18) . . ?
O1 C7 N1 119.5(3) . . ?
O1 C7 C1 121.3(3) . . ?
N1 C7 C1 119.1(3) . . ?
N2 N1 C7 114.2(2) . . ?
N2 N1 H1 127(3) . . ?
C7 N1 H1 117(3) . . ?
C8 N2 N1 123.1(2) . . ?
C8 N2 Zn 120.2(2) . . ?
N1 N2 Zn 116.42(18) . . ?
N2 C8 C11 113.3(2) . . ?
N2 C8 C9 125.1(3) . . ?
C11 C8 C9 121.6(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N21 C11 C61 121.3(3) . . ?
N21 C11 C8 115.7(3) . . ?
C61 C11 C8 123.0(3) . . ?
C31 N21 C11 119.5(3) . . ?
C31 N21 Zn 124.7(2) . . ?
C11 N21 Zn 115.9(2) . . ?
N21 C31 C41 122.8(3) . . ?
N21 C31 H31 118.6 . . ?
C41 C31 H31 118.6 . . ?
C51 C41 C31 117.7(3) . . ?
C51 C41 H41 121.1 . . ?
C31 C41 H41 121.1 . . ?
C41 C51 C61 119.9(3) . . ?
C41 C51 H51 120.0 . . ?
C61 C51 H51 120.0 . . ?
C51 C61 C11 118.7(3) . . ?
C51 C61 H61 120.6 . . ?
C11 C61 H61 120.6 . . ?
C1A O1A Zn 113.73(19) . . ?
O2A C1A O1A 123.0(3) . . ?
O2A C1A C2A 120.5(3) . . ?
O1A C1A C2A 116.5(3) . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
C1B O1B Zn 118.71(19) . . ?
O2B C1B O1B 124.7(3) . . ?
O2B C1B C2B 120.5(3) . . ?
O1B C1B C2B 114.8(3) . . ?
C1B C2B H2B1 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 109.5 . . ?
C1B C2B H2B3 109.5 . . ?
H2B1 C2B H2B3 109.5 . . ?
H2B2 C2B H2B3 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
C6 C1 C2 C3 -0.7(4) . . . . ?
C7 C1 C2 C3 175.5(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 N3 -178.4(3) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
N3 C4 C5 C6 178.3(3) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C7 C1 C6 C5 -175.5(3) . . . . ?
Zn O1 C7 N1 3.3(3) . . . . ?
Zn O1 C7 C1 -175.82(19) . . . . ?
C2 C1 C7 O1 -7.6(4) . . . . ?
C6 C1 C7 O1 168.4(3) . . . . ?
C2 C1 C7 N1 173.3(2) . . . . ?
C6 C1 C7 N1 -10.7(4) . . . . ?
O1 C7 N1 N2 1.5(4) . . . . ?
C1 C7 N1 N2 -179.4(2) . . . . ?
C7 N1 N2 C8 -179.9(2) . . . . ?
C7 N1 N2 Zn -5.6(3) . . . . ?
N1 N2 C8 C11 -178.8(2) . . . . ?
Zn N2 C8 C11 7.1(3) . . . . ?
N1 N2 C8 C9 1.0(4) . . . . ?
Zn N2 C8 C9 -173.1(2) . . . . ?
N2 C8 C11 N21 -3.6(4) . . . . ?
C9 C8 C11 N21 176.6(2) . . . . ?
N2 C8 C11 C61 176.8(3) . . . . ?
C9 C8 C11 C61 -3.0(4) . . . . ?
C61 C11 N21 C31 -0.4(4) . . . . ?
C8 C11 N21 C31 -179.9(2) . . . . ?
C61 C11 N21 Zn 178.3(2) . . . . ?
C8 C11 N21 Zn -1.3(3) . . . . ?
C11 N21 C31 C41 -1.4(4) . . . . ?
Zn N21 C31 C41 180.0(2) . . . . ?
N21 C31 C41 C51 1.7(5) . . . . ?
C31 C41 C51 C61 -0.1(5) . . . . ?
C41 C51 C61 C11 -1.6(5) . . . . ?
N21 C11 C61 C51 1.9(4) . . . . ?
C8 C11 C61 C51 -178.6(3) . . . . ?
Zn O1A C1A O2A 17.3(4) . . . . ?
Zn O1A C1A C2A -162.7(2) . . . . ?
Zn O1B C1B O2B -1.8(4) . . . . ?
Zn O1B C1B C2B 178.2(2) . . . . ?

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
N3 H3A O2B 0.85(4) 2.18(4) 3.001(4) 164(3) 1_456
N3 H3B O2B 0.87(5) 2.39(4) 3.195(4) 153(4) 2_556
N1 H1 O2A 0.71(4) 2.08(4) 2.784(4) 171(4) 2_566
C41 H41 O1A 0.95 2.44 3.380(4) 171.2 2_665

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.120

_shelxl_version_number           2013-2



