# 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_aq081
_database_code_depnum_ccdc_archive 'CCDC 2526168'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2026-05-05 deposited with the CCDC.	2026-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2025/1
_shelx_SHELXL_version_number     2025/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N4 O4 Zn'
_chemical_formula_sum            'C16 H16 N4 O4 Zn'
_chemical_formula_weight         393.70

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                   7.5192(2)
_cell_length_b                   8.8301(3)
_cell_length_c                   13.2595(4)
_cell_angle_alpha                81.2005(12)
_cell_angle_beta                 77.8018(12)
_cell_angle_gamma                73.6861(11)
_cell_volume                     821.72(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9160
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.15

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.524
_shelx_estimated_absorpt_T_min   0.640
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6530
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_absorpt_special_details   
'Additional spherical absorption correction applied with mu*r =  0.20'
_diffrn_ambient_temperature      200(2)
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_power             70
_diffrn_source_voltage           50
_diffrn_source_current           1.4
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Bruker PHOTON II 7 CCD detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            64300
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4055
_reflns_number_gt                3530
_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 Instrument Service V6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2019/3 (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2025/1 (Sheldrick, 2015b) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows V2023.1 (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were
placed in calculated positions and were included in the refinement in the riding
model approximation, with Uiso(H) set to 1.2 Ueq(C).

The H atoms of the methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015b)), with Uiso(H) set to
1.5Ueq(C).

A number of reflections with large differences between their observed and
calculated intensities were omitted. This is due to obstruction by the beam 
stop.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.2256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2025/1 (Sheldrick 2025)'
_refine_ls_extinction_coef       0.0100(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4055
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.001
_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
Zn1 Zn 0.69995(3) 0.30008(3) 0.27902(2) 0.02063(9) Uani 1 1 d . . . . .
O11 O 0.5032(2) 0.35076(18) 0.40257(12) 0.0250(3) Uani 1 1 d . . . . .
O12 O 0.3891(2) 0.5463(2) 0.28801(13) 0.0321(4) Uani 1 1 d . . . . .
O21 O 0.5785(2) 0.1926(2) 0.20547(12) 0.0295(4) Uani 1 1 d . . . . .
O22 O 0.8481(2) 0.1390(2) 0.09286(13) 0.0321(4) Uani 1 1 d . . . . .
N31 N 1.0801(3) 0.5386(2) 0.11090(14) 0.0263(4) Uani 1 1 d . . . . .
N32 N 0.8362(2) 0.4582(2) 0.19926(14) 0.0231(4) Uani 1 1 d . . . . .
N41 N 1.1810(3) 0.0157(2) 0.38638(15) 0.0265(4) Uani 1 1 d . . . . .
N42 N 0.9124(2) 0.1287(2) 0.33388(14) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.1788(3) 0.4845(2) 0.43951(16) 0.0193(4) Uani 1 1 d . . . . .
C12 C 0.1591(3) 0.4240(2) 0.54351(16) 0.0217(4) Uani 1 1 d . . . . .
H12 H 0.267662 0.372023 0.573260 0.026 Uiso 1 1 calc R U . . .
C13 C -0.0189(3) 0.4396(2) 0.60364(16) 0.0209(4) Uani 1 1 d . . . . .
H13 H -0.031850 0.398387 0.674553 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3704(3) 0.4621(2) 0.37107(17) 0.0223(4) Uani 1 1 d . . . . .
C21 C 0.5875(3) 0.0640(2) 0.05954(16) 0.0206(4) Uani 1 1 d . . . . .
C22 C 0.4085(3) 0.0424(3) 0.09761(16) 0.0234(4) Uani 1 1 d . . . . .
H22 H 0.345916 0.071050 0.164738 0.028 Uiso 1 1 calc R U . . .
C23 C 0.3203(3) -0.0205(3) 0.03849(17) 0.0241(4) Uani 1 1 d . . . . .
H23 H 0.197404 -0.033903 0.064770 0.029 Uiso 1 1 calc R U . . .
C24 C 0.6824(3) 0.1357(2) 0.12235(16) 0.0229(4) Uani 1 1 d . . . . .
C31 C 1.0184(3) 0.4152(3) 0.16136(17) 0.0268(5) Uani 1 1 d . . . . .
H31 H 1.095456 0.310034 0.169072 0.032 Uiso 1 1 calc R U . . .
C32 C 0.7794(3) 0.6184(3) 0.17029(18) 0.0276(5) Uani 1 1 d . . . . .
H32 H 0.654744 0.683112 0.186223 0.033 Uiso 1 1 calc R U . . .
C33 C 0.9295(3) 0.6697(3) 0.11534(19) 0.0296(5) Uani 1 1 d . . . . .
H33 H 0.930022 0.774718 0.086032 0.036 Uiso 1 1 calc R U . . .
C34 C 1.2761(3) 0.5326(3) 0.0628(2) 0.0367(6) Uani 1 1 d . . . . .
H34A H 1.283922 0.562633 -0.011949 0.055 Uiso 1 1 calc R U . . .
H34B H 1.354841 0.424715 0.074965 0.055 Uiso 1 1 calc R U . . .
H34C H 1.320554 0.606440 0.093313 0.055 Uiso 1 1 calc R U . . .
C41 C 1.0389(3) 0.1470(3) 0.38318(18) 0.0261(4) Uani 1 1 d . . . . .
H41 H 1.030465 0.240985 0.412533 0.031 Uiso 1 1 calc R U . . .
C42 C 0.9775(3) -0.0231(3) 0.30492(19) 0.0277(5) Uani 1 1 d . . . . .
H42 H 0.915567 -0.070927 0.268163 0.033 Uiso 1 1 calc R U . . .
C43 C 1.1438(3) -0.0938(3) 0.33690(19) 0.0290(5) Uani 1 1 d . . . . .
H43 H 1.219138 -0.198369 0.326945 0.035 Uiso 1 1 calc R U . . .
C44 C 1.3503(4) -0.0030(3) 0.4296(2) 0.0412(6) Uani 1 1 d . . . . .
H44A H 1.376308 -0.104659 0.472638 0.062 Uiso 1 1 calc R U . . .
H44B H 1.330800 0.083679 0.472204 0.062 Uiso 1 1 calc R U . . .
H44C H 1.457375 -0.000675 0.373071 0.062 Uiso 1 1 calc R U . . .


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 2.00 -3.00 0.0250
-2.00 -3.00 2.00 0.1170
-2.00 0.00 -3.00 0.0770
-1.00 1.00 4.00 0.1510
-1.00 -1.00 -4.00 0.1360
0.00 3.00 2.00 0.1110
0.00 4.00 -1.00 0.0560
0.00 0.00 1.00 0.1230
0.00 3.00 -4.00 0.0830
1.00 0.00 -4.00 0.1670
1.00 -3.00 2.00 0.0610
1.00 3.00 -1.00 0.0760
1.00 -2.00 4.00 0.0570
2.00 -2.00 3.00 0.0200
2.00 3.00 2.00 0.0910
2.00 3.00 4.00 0.1050
2.00 -3.00 -3.00 0.1290
3.00 3.00 -1.00 0.1130
4.00 3.00 2.00 0.0880
4.00 1.00 0.00 0.1090

_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
Zn1 O21 1.9575(15) . ?
Zn1 O11 1.9752(15) . ?
Zn1 N32 2.0027(18) . ?
Zn1 N42 2.0411(18) . ?
O11 C14 1.279(3) . ?
O12 C14 1.236(3) . ?
O21 C24 1.289(3) . ?
O22 C24 1.232(3) . ?
N31 C31 1.334(3) . ?
N31 C33 1.372(3) . ?
N31 C34 1.466(3) . ?
N32 C31 1.323(3) . ?
N32 C32 1.377(3) . ?
N41 C41 1.340(3) . ?
N41 C43 1.367(3) . ?
N41 C44 1.463(3) . ?
N42 C41 1.319(3) . ?
N42 C42 1.376(3) . ?
C11 C12 1.393(3) . ?
C11 C13 1.394(3) 2_566 ?
C11 C14 1.510(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C21 C22 1.390(3) . ?
C21 C23 1.393(3) 2_655 ?
C21 C24 1.506(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.359(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C41 H41 0.9500 . ?
C42 C43 1.355(3) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 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
O21 Zn1 O11 100.54(7) . . ?
O21 Zn1 N32 119.36(7) . . ?
O11 Zn1 N32 122.27(7) . . ?
O21 Zn1 N42 106.26(7) . . ?
O11 Zn1 N42 104.70(7) . . ?
N32 Zn1 N42 102.06(7) . . ?
C14 O11 Zn1 106.12(13) . . ?
C24 O21 Zn1 114.49(14) . . ?
C31 N31 C33 107.74(18) . . ?
C31 N31 C34 125.1(2) . . ?
C33 N31 C34 127.1(2) . . ?
C31 N32 C32 105.64(18) . . ?
C31 N32 Zn1 121.21(15) . . ?
C32 N32 Zn1 133.15(15) . . ?
C41 N41 C43 107.65(18) . . ?
C41 N41 C44 125.9(2) . . ?
C43 N41 C44 126.3(2) . . ?
C41 N42 C42 105.68(18) . . ?
C41 N42 Zn1 127.84(15) . . ?
C42 N42 Zn1 124.91(15) . . ?
C12 C11 C13 119.66(18) . 2_566 ?
C12 C11 C14 121.08(18) . . ?
C13 C11 C14 119.19(19) 2_566 . ?
C13 C12 C11 120.04(19) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C11 120.30(19) . 2_566 ?
C12 C13 H13 119.8 . . ?
C11 C13 H13 119.8 2_566 . ?
O12 C14 O11 124.13(19) . . ?
O12 C14 C11 119.38(19) . . ?
O11 C14 C11 116.45(18) . . ?
C22 C21 C23 119.59(19) . 2_655 ?
C22 C21 C24 120.88(19) . . ?
C23 C21 C24 119.53(19) 2_655 . ?
C23 C22 C21 120.59(19) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C21 119.82(19) . 2_655 ?
C22 C23 H23 120.1 . . ?
C21 C23 H23 120.1 2_655 . ?
O22 C24 O21 124.1(2) . . ?
O22 C24 C21 120.28(19) . . ?
O21 C24 C21 115.63(18) . . ?
N32 C31 N31 111.3(2) . . ?
N32 C31 H31 124.4 . . ?
N31 C31 H31 124.4 . . ?
C33 C32 N32 109.4(2) . . ?
C33 C32 H32 125.3 . . ?
N32 C32 H32 125.3 . . ?
C32 C33 N31 105.9(2) . . ?
C32 C33 H33 127.1 . . ?
N31 C33 H33 127.1 . . ?
N31 C34 H34A 109.5 . . ?
N31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N42 C41 N41 111.09(19) . . ?
N42 C41 H41 124.5 . . ?
N41 C41 H41 124.5 . . ?
C43 C42 N42 109.5(2) . . ?
C43 C42 H42 125.2 . . ?
N42 C42 H42 125.2 . . ?
C42 C43 N41 106.08(19) . . ?
C42 C43 H43 127.0 . . ?
N41 C43 H43 127.0 . . ?
N41 C44 H44A 109.5 . . ?
N41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
C13 C11 C12 C13 -0.1(3) 2_566 . . . ?
C14 C11 C12 C13 -176.96(18) . . . . ?
C11 C12 C13 C11 0.1(3) . . . 2_566 ?
Zn1 O11 C14 O12 -17.9(3) . . . . ?
Zn1 O11 C14 C11 159.57(14) . . . . ?
C12 C11 C14 O12 -163.1(2) . . . . ?
C13 C11 C14 O12 20.0(3) 2_566 . . . ?
C12 C11 C14 O11 19.2(3) . . . . ?
C13 C11 C14 O11 -157.63(19) 2_566 . . . ?
C23 C21 C22 C23 -0.6(4) 2_655 . . . ?
C24 C21 C22 C23 178.6(2) . . . . ?
C21 C22 C23 C21 0.6(4) . . . 2_655 ?
Zn1 O21 C24 O22 3.9(3) . . . . ?
Zn1 O21 C24 C21 -175.24(14) . . . . ?
C22 C21 C24 O22 172.4(2) . . . . ?
C23 C21 C24 O22 -8.4(3) 2_655 . . . ?
C22 C21 C24 O21 -8.5(3) . . . . ?
C23 C21 C24 O21 170.81(19) 2_655 . . . ?
C32 N32 C31 N31 0.4(3) . . . . ?
Zn1 N32 C31 N31 179.80(15) . . . . ?
C33 N31 C31 N32 -0.5(3) . . . . ?
C34 N31 C31 N32 177.8(2) . . . . ?
C31 N32 C32 C33 -0.2(3) . . . . ?
Zn1 N32 C32 C33 -179.50(17) . . . . ?
N32 C32 C33 N31 -0.1(3) . . . . ?
C31 N31 C33 C32 0.3(3) . . . . ?
C34 N31 C33 C32 -177.9(2) . . . . ?
C42 N42 C41 N41 0.4(3) . . . . ?
Zn1 N42 C41 N41 -165.73(15) . . . . ?
C43 N41 C41 N42 -0.3(3) . . . . ?
C44 N41 C41 N42 176.4(2) . . . . ?
C41 N42 C42 C43 -0.3(3) . . . . ?
Zn1 N42 C42 C43 166.31(16) . . . . ?
N42 C42 C43 N41 0.2(3) . . . . ?
C41 N41 C43 C42 0.1(3) . . . . ?
C44 N41 C43 C42 -176.6(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
_geom_hbond_publ_flag
C43 H43 O12 0.95 2.33 3.279(3) 174 1_645 yes
C44 H44A O11 0.98 2.59 3.555(3) 168 2_756 yes

_refine_diff_density_max         0.858
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.075

