# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_zn5_0m_5_sq
_database_code_depnum_ccdc_archive 'CCDC 2143879'
loop_
_audit_author_name
_audit_author_address
'Rais Ahmad Khan'
;King Saud University
Saudi Arabia
;
_audit_update_record             
;
2022-01-23 deposited with the CCDC.	2023-12-08 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         'C22 H14 N10 O12 Zn3, [+ solvent]'
_chemical_formula_sum            'C22 H14 N10 O12 Zn3'
_chemical_formula_weight         806.54

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   20.2481(19)
_cell_length_b                   16.8091(19)
_cell_length_c                   15.4170(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.646(4)
_cell_angle_gamma                90
_cell_volume                     5241.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8323
_cell_measurement_theta_min      2.4277
_cell_measurement_theta_max      28.2452

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.022
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.406
_shelx_estimated_absorpt_T_min   0.512
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.626617
_exptl_absorpt_correction_T_max  0.745686
_exptl_absorpt_process_details   
;
TWINABS 2012/1: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            34720
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.761
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6492
_reflns_number_gt                4986
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Apex4 v2021.10-RC6 (Bruker, 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1275(Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The crystal under investigation was found to be non-merohedrally 
twinned. The orientation matrices for the two components were 
identified using the program Cell_Now, with the two components 
being related by a 180 degree rotation around the real c-axis. 
The two components were integrated using Saint and corrected 
for absorption using twinabs, resulting in the following 
statistics:

13106 data (2845 unique) involve domain 1 only, mean I/sigma 10.0
13069 data (2855 unique) involve domain 2 only, mean I/sigma 5.6
22002 data (5444 unique) involve 2 domains, mean I/sigma 8.6

The exact twin matrix identified by the integration program was 
found to be: 

-0.99999  0.00018 -0.12315
-0.00010 -1.00000 -0.00066
-0.00019 -0.00055  0.99999

The structure was solved using direct methods with only the 
non-overlapping reflections of component 1. The structure was 
refined using the hklf 5 routine with all reflections of component 
1 (including the overlapping ones), resulting in a BASF value of 
0.250(1).

The Rint value given is for all reflections and is based on 
agreement between observed single and composite intensities 
and those calculated from refined unique intensities and twin 
fractions (TWINABS (Sheldrick, 2012)).

One of the nitrogen heterocycles is disordered by a slight tilt. The 
two disordered moieties were restrained to have similar geometries 
and both were restrained to be close to planar. Atom N1 was excluded 
from the disorder. Uij components of ADPs for disordered atoms closer 
to each other than 2.0 Angstrom were restrained to be similar. 
Subject to these conditions the occupancy ratio refined to 0.53(2) 
to 0.47(2). 

In addition to twinning, the structure also exhibits large volume 
sections (ca. 53.4 % oif the unit cell volume) consisting of highly 
disordered solvate or other small molecules. No satisfactory model 
for the solvate molecules could be developed, and the contribution 
of the solvate molecules was instead taken into account by reverse 
Fourier transform methods. The data were first detwinned (using the 
LIST 8 function of Shelxl2018) and then the cif and fcf files were 
subjected to the SQUEEZE routine as implemented in the program Platon. 
The resultant files were used in the further refinement. (Both the 
hklf 5 type HKL file and the detwinned FAB file are appended to this 
cif file). A volume of 2797 cubic Angstrom per unit cell containing 
690 electrons was corrected for.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+28.2678P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6492
_refine_ls_number_parameters     271
_refine_ls_number_restraints     235
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.059
_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 0.58869(2) 0.48423(4) 0.52013(3) 0.03629(18) Uani 1 1 d . . . . .
Zn2 Zn 0.500000 0.74828(5) 0.750000 0.03191(19) Uani 1 2 d DS T P . .
O1 O 0.64539(17) 0.5181(3) 0.4299(2) 0.0654(14) Uani 1 1 d . . . . .
O4 O 0.91365(17) 0.7024(2) 0.2295(2) 0.0492(10) Uani 1 1 d . . . . .
O5 O 0.69956(19) 0.6384(3) 0.0597(2) 0.0568(12) Uani 1 1 d . . . . .
O6 O 0.63428(17) 0.5543(3) 0.1256(2) 0.0465(10) Uani 1 1 d . . . . .
N1 N 0.50412(18) 0.6743(2) 0.6474(2) 0.0316(7) Uani 0.53(2) 1 d D U P A 1
C10 C 0.5534(5) 0.6264(8) 0.6208(8) 0.0313(19) Uani 0.53(2) 1 d D U P A 1
N2 N 0.5353(8) 0.5727(11) 0.5618(11) 0.0320(19) Uani 0.53(2) 1 d D U P A 1
N3 N 0.4666(6) 0.5851(8) 0.5463(8) 0.032(2) Uani 0.53(2) 1 d D U P A 1
C11 C 0.4520(5) 0.6442(8) 0.5971(8) 0.031(2) Uani 0.53(2) 1 d D U P A 1
N4 N 0.6174(4) 0.6354(8) 0.6505(11) 0.049(3) Uani 0.53(2) 1 d D U P A 1
H4A H 0.648493 0.604794 0.630313 0.059 Uiso 0.53(2) 1 calc R U P A 1
H4B H 0.627738 0.671803 0.689843 0.059 Uiso 0.53(2) 1 calc R U P A 1
N5 N 0.3880(4) 0.6713(8) 0.6027(7) 0.034(2) Uani 0.53(2) 1 d D U P A 1
H5A H 0.355668 0.648662 0.571588 0.041 Uiso 0.53(2) 1 calc R U P A 1
H5B H 0.379484 0.711151 0.637499 0.041 Uiso 0.53(2) 1 calc R U P A 1
N1B N 0.50412(18) 0.6743(2) 0.6474(2) 0.0316(7) Uani 0.47(2) 1 d D U P A 2
C10B C 0.5527(5) 0.6211(9) 0.6388(9) 0.033(2) Uani 0.47(2) 1 d D U P A 2
N2B N 0.5387(8) 0.5737(13) 0.5715(12) 0.032(2) Uani 0.47(2) 1 d D U P A 2
N3B N 0.4761(7) 0.6002(9) 0.5370(9) 0.030(2) Uani 0.47(2) 1 d D U P A 2
C11B C 0.4581(6) 0.6587(9) 0.5851(9) 0.034(2) Uani 0.47(2) 1 d D U P A 2
N4B N 0.6092(6) 0.6153(9) 0.6902(10) 0.045(3) Uani 0.47(2) 1 d D U P A 2
H4BA H 0.638714 0.578543 0.679509 0.054 Uiso 0.47(2) 1 calc R U P A 2
H4BB H 0.616109 0.648228 0.734016 0.054 Uiso 0.47(2) 1 calc R U P A 2
N5B N 0.4021(7) 0.7043(9) 0.5737(10) 0.050(3) Uani 0.47(2) 1 d D U P A 2
H5BA H 0.373978 0.694934 0.529656 0.060 Uiso 0.47(2) 1 calc R U P A 2
H5BB H 0.394391 0.742984 0.610345 0.060 Uiso 0.47(2) 1 calc R U P A 2
C1 C 0.7342(3) 0.5756(3) 0.3621(3) 0.0399(11) Uani 1 1 d . . . . .
O2 O 0.7274(3) 0.5598(4) 0.5149(3) 0.103(2) Uani 1 1 d . . . . .
O3 O 0.9353(2) 0.6431(3) 0.3545(3) 0.0587(12) Uani 1 1 d . . . . .
C2 C 0.7993(3) 0.6028(3) 0.3644(3) 0.0427(12) Uani 1 1 d . . . . .
H2 H 0.825003 0.602087 0.417508 0.051 Uiso 1 1 calc R U . . .
C3 C 0.8270(2) 0.6310(3) 0.2892(3) 0.0393(11) Uani 1 1 d . . . . .
C4 C 0.7894(2) 0.6322(3) 0.2111(3) 0.0384(11) Uani 1 1 d . . . . .
H4 H 0.807676 0.652784 0.160131 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7247(2) 0.6029(3) 0.2081(3) 0.0347(10) Uani 1 1 d . . . . .
C6 C 0.6980(2) 0.5745(3) 0.2836(3) 0.0362(11) Uani 1 1 d . . . . .
H6 H 0.654291 0.553917 0.281319 0.043 Uiso 1 1 calc R U . . .
C7 C 0.7015(3) 0.5486(4) 0.4432(3) 0.0459(13) Uani 1 1 d . . . . .
C8 C 0.8970(3) 0.6606(3) 0.2931(3) 0.0439(13) Uani 1 1 d . . . . .
C9 C 0.6838(2) 0.6005(3) 0.1237(3) 0.0384(11) 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
Zn1 N3 1.885(12) 5_666 ?
Zn1 O1 1.930(4) . ?
Zn1 O6 1.944(3) 6_566 ?
Zn1 N2 1.964(12) . ?
Zn1 N2B 1.997(13) . ?
Zn1 N3B 2.099(13) 5_666 ?
Zn2 O4 1.948(3) 7_666 ?
Zn2 O4 1.948(3) 8_466 ?
Zn2 N1B 2.017(4) . ?
Zn2 N1 2.017(4) . ?
Zn2 N1 2.017(4) 2_656 ?
O1 C7 1.254(7) . ?
O4 C8 1.264(6) . ?
O5 C9 1.229(6) . ?
O6 C9 1.269(6) . ?
N1 C10 1.361(10) . ?
N1 C11 1.377(10) . ?
C10 N2 1.321(11) . ?
C10 N4 1.363(10) . ?
N2 N3 1.416(10) . ?
N3 C11 1.308(11) . ?
C11 N5 1.379(10) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N1B C11B 1.333(11) . ?
N1B C10B 1.341(11) . ?
C10B N2B 1.328(12) . ?
C10B N4B 1.365(11) . ?
N2B N3B 1.423(12) . ?
N3B C11B 1.294(11) . ?
C11B N5B 1.374(11) . ?
N4B H4BA 0.8800 . ?
N4B H4BB 0.8800 . ?
N5B H5BA 0.8800 . ?
N5B H5BB 0.8800 . ?
C1 C6 1.385(6) . ?
C1 C2 1.395(7) . ?
C1 C7 1.511(7) . ?
O2 C7 1.216(6) . ?
O3 C8 1.232(5) . ?
C2 C3 1.393(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(6) . ?
C3 C8 1.501(7) . ?
C4 C5 1.397(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(6) . ?
C5 C9 1.511(6) . ?
C6 H6 0.9500 . ?

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
N3 Zn1 O1 98.6(4) 5_666 . ?
N3 Zn1 O6 119.7(5) 5_666 6_566 ?
O1 Zn1 O6 115.22(15) . 6_566 ?
N3 Zn1 N2 108.9(4) 5_666 . ?
O1 Zn1 N2 111.6(7) . . ?
O6 Zn1 N2 103.0(5) 6_566 . ?
O1 Zn1 N2B 113.2(8) . . ?
O6 Zn1 N2B 98.6(5) 6_566 . ?
N3 Zn1 N3B 8.1(7) 5_666 5_666 ?
O1 Zn1 N3B 106.2(4) . 5_666 ?
O6 Zn1 N3B 112.9(4) 6_566 5_666 ?
N2 Zn1 N3B 107.8(7) . 5_666 ?
N2B Zn1 N3B 110.9(5) . 5_666 ?
O4 Zn2 O4 129.6(2) 7_666 8_466 ?
O4 Zn2 N1B 108.66(16) 7_666 . ?
O4 Zn2 N1B 101.81(14) 8_466 . ?
O4 Zn2 N1 108.66(16) 7_666 . ?
O4 Zn2 N1 101.81(14) 8_466 . ?
O4 Zn2 N1 101.81(14) 7_666 2_656 ?
O4 Zn2 N1 108.67(16) 8_466 2_656 ?
N1 Zn2 N1 103.9(2) . 2_656 ?
C7 O1 Zn1 124.6(3) . . ?
C8 O4 Zn2 112.4(3) . 7_666 ?
C9 O6 Zn1 121.9(3) . 6_565 ?
C10 N1 C11 99.6(7) . . ?
C10 N1 Zn2 131.2(5) . . ?
C11 N1 Zn2 127.6(5) . . ?
N2 C10 N1 115.3(8) . . ?
N2 C10 N4 122.5(10) . . ?
N1 C10 N4 122.2(10) . . ?
C10 N2 N3 104.8(9) . . ?
C10 N2 Zn1 127.1(9) . . ?
N3 N2 Zn1 127.4(9) . . ?
C11 N3 N2 105.0(9) . . ?
C11 N3 Zn1 130.5(8) . 5_666 ?
N2 N3 Zn1 123.7(9) . 5_666 ?
N3 C11 N1 115.3(8) . . ?
N3 C11 N5 121.8(9) . . ?
N1 C11 N5 122.8(9) . . ?
C10 N4 H4A 120.0 . . ?
C10 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C11 N5 H5A 120.0 . . ?
C11 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C11B N1B C10B 106.8(8) . . ?
C11B N1B Zn2 129.3(6) . . ?
C10B N1B Zn2 123.1(6) . . ?
N2B C10B N1B 110.3(9) . . ?
N2B C10B N4B 123.6(11) . . ?
N1B C10B N4B 126.1(11) . . ?
C10B N2B N3B 105.0(10) . . ?
C10B N2B Zn1 131.9(10) . . ?
N3B N2B Zn1 123.1(9) . . ?
C11B N3B N2B 107.0(10) . . ?
N3B C11B N1B 110.9(9) . . ?
N3B C11B N5B 127.1(10) . . ?
N1B C11B N5B 121.8(10) . . ?
C10B N4B H4BA 120.0 . . ?
C10B N4B H4BB 120.0 . . ?
H4BA N4B H4BB 120.0 . . ?
C11B N5B H5BA 120.0 . . ?
C11B N5B H5BB 120.0 . . ?
H5BA N5B H5BB 120.0 . . ?
C6 C1 C2 119.1(5) . . ?
C6 C1 C7 119.0(5) . . ?
C2 C1 C7 121.9(4) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 C8 119.6(4) . . ?
C4 C3 C8 120.5(4) . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 C9 119.5(4) . . ?
C4 C5 C9 121.0(4) . . ?
C1 C6 C5 121.1(4) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O2 C7 O1 124.2(5) . . ?
O2 C7 C1 121.2(5) . . ?
O1 C7 C1 114.6(4) . . ?
O3 C8 O4 123.2(5) . . ?
O3 C8 C3 120.8(5) . . ?
O4 C8 C3 116.0(4) . . ?
O5 C9 O6 124.8(4) . . ?
O5 C9 C5 121.7(4) . . ?
O6 C9 C5 113.5(4) . . ?

_refine_diff_density_max         0.634
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.094




