research communications
κN1)bis(3-aminopyrazole-κN2)bis(nitrato-κO)copper(II)
and Hirshfeld surface analysis of bis(3-aminopyrazole-aDepartment of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska St. 64/13, Kyiv 01601, Ukraine, bInnovation Development Center ABN, Pirogov St. 2/37, 01030 Kyiv, Ukraine, cBakul Institute for Superhard Materials, National Academy of Sciences of Ukraine, Avtozavodskaya St. 2, Kyiv 04074, Ukraine, and dDepartment of Chemistry, Kyiv National University of Construction and Architecture, Povitroflotsky Ave. 31, Kyiv 03680, Ukraine
*Correspondence e-mail: olesia.kucheriv@univ.kiev.ua
In the 3)2(C3H5N3)4], the CuII atom is situated on an inversion center (Wyckoff position 2c of P21/n) and shows an octahedral [N4O2] coordination environment. The axial positions are occupied by O atoms of nitrate anions, while the equatorial positions are taken up by the N atoms of four 3-aminopyrazole ligands. As a result of the of the latter, two coordinate with the N1-atom of 3-aminopyrazole while the other two with the N2-atom. The presence of pyrrole-like N—H groups and amine substituents as donor groups leads to numerous intra- and intermolecular hydrogen-bonding interactions, which were quantified by Hirshfeld surface analysis.
of the title compound, [Cu(NOKeywords: crystal structure; pyrazole complex; copper(II); Jahn–Teller distortion.
CCDC reference: 2302897
1. Chemical context
Supramolecular chemistry includes an extensive domain of pyrazole complexes, the main feature of which revolves around the formation of intra- and intermolecular hydrogen bonds (Pérez & Riera, 2009). Pyrazole is a heterocyclic compound that contains two types of N atoms. One of the N atoms is termed pyridine-like because it donates one p-electron to the aromatic ring while its lone pair of electrons is non-conjugated. The other N atom is described as acidic pyrrole-like as it contributes two p-electrons of the lone pair to the aromatic ring, which consequently is distributed around the ring (Reedijk, 1987).
The presence of both pyridine-like and pyrrole-like N atoms makes a pyrazole molecule both basic and acidic. With respect to the Brønsted–Lowry theory, this ligand is et al., 2001; Titi et al., 2023), antibacterial (Zaimović et al., 2022), antifungal (Titi et al., 2023) and antitumor (Ruan et al., 2012) activities.
Pyrazolate anions, which are the deprotonated form of pyrazole, form an individual class of ligands which, in contrast to pyrazole itself, can act as bridging. Apart from its ability to donate or accept a proton, an important feature of pyrazole is its tendency to from extensive networks of hydrogen bonds, in particular due to the simultaneous presence of a hydrogen-donating N—H group and a hydrogen-accepting pyridine-like N atom. The existence of these two groups allows the formation of intermolecular N—H⋯N contacts and makes pyrazole an important molecule for supramolecular chemistry. In addition, numerous examples of practical applications have been offered for pyrazole-containing coordination compounds. For example, copper(II) complexes with pyrazole-containing ligands have been shown to exhibit catalytic (GamezHere we describe the 3H5N3)4(NO3)2].
of a new copper(II) complex with 3-aminopyrazole as a ligand, namely [Cu(C2. Structural commentary
The title compound is a molecular coordination compound, where the central CuII atom is situated at an inversion center (Wyckoff position 2c of P21/n) with an octahedral [N4O2] coordination environment. The axial positions are occupied by two oxygen atoms from nitrato ligands [Cu1—O2 = 2.5544 (19) Å, which is a typical value observed in Cu—(nitrato)− complexes] and the equatorial positions are occupied by four pyridine-like nitrogen atoms of 3-aminopyrazole (Fig. 1). Two of the four 3-aminopyrazole ligands coordinate with the N1 atom [Cu1—N4 = 1.975 (2) Å] while the other two coordinate with the N2 atom [Cu1—N1 = 2.0331 (17) Å]. The different type of N-coordination in the title compound is an illustrative example of in 3-aminopyrazole. This effect leads to the formation of more complex and diverse frameworks and expands the potential number of possible coordination compounds that can be formed in comparison with only one type of ligand. The notable difference in the Cu—O and Cu—N bond lengths leads to an elongation of the coordination octahedron, which is associated with the Jahn–Teller effect that is commonly observed for CuII complexes. The length distortion parameter ζ = |(Cu – Li) – <Cu – L>| (where L = ligand) for this structure is 1.468 Å. The deviation from an ideal octahedron for twelve cis-L—Cu—L angles can be described by the octahedral distortion parameter Σ = |90° – αi| = 17.33°. Pyrazole rings with the same type of coordination are located in one plane, while the angle between pyrazole rings with different types of coordination is 98.67 (11)°. The angle between the CuN4 and (N4/N5/C4–C6) planes is 16.9 (1)° while between the CuN4 and (N1/N2/C1–C3) planes, the corresponding angle is 101.48 (10)°. Intramolecular hydrogen bonds stabilize the molecular structure and include N—H⋯O contacts between 3-aminopyrazole molecules and the O atoms of the nitrato ligand as well as N—H⋯N contacts between the pyrrole-like N atom of one of the organic ligands and the amino group of another 3-aminopyrazole ligand (Fig. 1, Table 1).
3. Supramolecular features
Molecules of the title coordination compound interact with each other through a set of intermolecular interactions, creating a supramolecular tri-periodic network (Fig. 2). Intermolecular hydrogen bonds include N—H⋯O contacts between 3-aminopyrazole ligands and nitrate anions of a neighboring complex, as well as weak C—H⋯N contacts (Fig. 2). Numerical data of these hydrogen-bonding interactions is collated in Table 1.
4. Hirshfeld surface analysis
A Hirshfeld surface analysis was performed using CrystalExplorer (Spackman et al., 2021) with a standard resolution of the three-dimensional dnorm surfaces plotted over a fixed color scale. The associated two-dimensional fingerprint plots were also generated. The Hirshfeld surface of the title compound demonstrates the presence of strong intermolecular N—H⋯O hydrogen bonds between coordinating nitrate anions and neighboring 3-aminopyrazole molecules, as shown in Fig. 3a in red. Fig. 3b additionally demonstrates the presence of much weaker C—H⋯N contacts. Fingerprint plots are given for contacts with the highest contribution to the structure (Fig. 3c–f). The most important contributions for the crystal packing are from O⋯H (32.6%), C⋯H (14.1%) and N⋯H (12.9%) contacts. H⋯H interactions are not shown. The de and di values presented on the axes of the fingerprint plots are the distances to the closest external and internal atoms from a selected point to the Hirshfeld surface. It is worth noting that the fingerprint plots highlight the most frequently occurring weak interactions within the structure, whereas the graphical depiction of the surface emphasizes the strongest interactions.
5. Database survey
According to a search of the Cambridge Structural Database (CSD, version 5.43, last update March 2022; Groom et al., 2016), there are only two records of copper(II) complexes containing 3-aminopyrazole as a ligand: TIXDAH (Świtlicka-Olszewska et al., 2014) and QIJSAF (Wang et al., 2014). TIXDAH is [Cu(C2O4)(3-aminopyrazole)2]·3H2O, in which CuII has a square-pyramidal [N3O2] coordination environment. The basal positions are occupied by the O atoms of a bidentate oxalate anion and two ring N atoms of two aminopyrazole ligands, and the apical positions by the N atom of the amino group of another aminopyrazole ligand. Similar to the title compound, the aminopyrazole molecules display different types of coordination – with N1 or N2 atoms. QIJSAF is [Cu(3-aminopyrazole)(2,6-pyridinedicarboxylato)(H2O)]·H2O, in which CuII has a distorted octahedral [N2O4] environment. The equatorial positions are occupied by one N2-coordinating 3-aminopyrazole and a tridentate 2,6-pyridinedicarboxylate ligand while the axial positions are taken up by one water molecule and one carboxylate O atom of another ligand.
6. Synthesis and crystallization
20 mg (0.1 mmol) of Cu(NO3)2 in 200 µl of water were mixed with 42 mg (0.5 mmol) of 3-aminopyrazole in 200 µl of water. The obtained solution was left to evaporate in air. Within 24 h, blue crystals were collected from the reaction mixture and kept in the mother solution prior to the X-ray measurement.
7. Refinement
Crystal data, data collection and structure . All H atoms were found from a difference-Fourier map and refined isotropically with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.2Ueq(N).
details are summarized in Table 2
|
Supporting information
CCDC reference: 2302897
https://doi.org/10.1107/S2056989023009295/wm5699sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023009295/wm5699Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2023); cell
CrysAlis PRO (Rigaku OD, 2023); data reduction: CrysAlis PRO (Rigaku OD, 2023); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).[Cu(NO3)2(C3H5N3)4] | F(000) = 534 |
Mr = 519.96 | Dx = 1.634 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 8.83222 (18) Å | Cell parameters from 4669 reflections |
b = 9.9714 (2) Å | θ = 5.0–75.6° |
c = 12.1043 (2) Å | µ = 2.05 mm−1 |
β = 97.6408 (19)° | T = 200 K |
V = 1056.55 (4) Å3 | Prism, clear light blue |
Z = 2 | 0.10 × 0.10 × 0.05 mm |
XtaLAB Synergy, Dualflex, HyPix diffractometer | 2023 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 1903 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.025 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 76.0°, θmin = 5.8° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2023) | k = −12→11 |
Tmin = 0.631, Tmax = 1.000 | l = −14→14 |
6493 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Only H-atom coordinates refined |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0689P)2 + 0.4789P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
2023 reflections | Δρmax = 0.45 e Å−3 |
181 parameters | Δρmin = −0.43 e Å−3 |
Geometry. 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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.500000 | 0.000000 | 0.500000 | 0.03217 (18) | |
N5 | 0.4258 (2) | −0.05809 (18) | 0.72784 (15) | 0.0330 (4) | |
N4 | 0.3930 (2) | 0.01620 (18) | 0.63262 (17) | 0.0353 (4) | |
O3 | 0.7519 (2) | 0.40655 (17) | 0.58858 (17) | 0.0561 (5) | |
N7 | 0.7646 (2) | 0.28338 (19) | 0.59003 (16) | 0.0417 (5) | |
O1 | 0.8905 (2) | 0.2305 (2) | 0.6228 (2) | 0.0625 (5) | |
C1 | 0.3111 (3) | 0.2405 (2) | 0.38736 (18) | 0.0359 (5) | |
N1 | 0.3312 (2) | 0.11018 (18) | 0.41243 (15) | 0.0354 (4) | |
O2 | 0.6506 (3) | 0.2110 (2) | 0.5642 (2) | 0.0702 (7) | |
N6 | 0.3538 (3) | −0.0813 (2) | 0.90865 (17) | 0.0442 (5) | |
N2 | 0.1924 (2) | 0.0519 (2) | 0.38069 (19) | 0.0469 (5) | |
C4 | 0.3441 (3) | −0.0178 (2) | 0.80771 (19) | 0.0341 (5) | |
C5 | 0.2547 (3) | 0.0873 (3) | 0.7639 (2) | 0.0488 (6) | |
C6 | 0.2881 (3) | 0.1034 (3) | 0.6570 (2) | 0.0498 (6) | |
C2 | 0.1602 (3) | 0.2639 (3) | 0.3389 (2) | 0.0443 (5) | |
C3 | 0.0907 (3) | 0.1423 (3) | 0.3363 (2) | 0.0516 (6) | |
N3 | 0.4272 (3) | 0.3290 (2) | 0.4016 (2) | 0.0530 (5) | |
H3A | 0.499 (4) | 0.306 (4) | 0.465 (3) | 0.064* | |
H3B | 0.400 (4) | 0.422 (4) | 0.393 (3) | 0.064* | |
H6A | 0.434 (4) | −0.132 (4) | 0.927 (3) | 0.064* | |
H6B | 0.323 (4) | −0.034 (4) | 0.962 (3) | 0.064* | |
H2 | 0.177 (4) | −0.029 (4) | 0.385 (3) | 0.064* | |
H5 | 0.488 (4) | −0.116 (4) | 0.731 (3) | 0.064* | |
H3 | −0.016 (4) | 0.117 (3) | 0.296 (3) | 0.064* | |
H6 | 0.254 (4) | 0.165 (4) | 0.609 (3) | 0.064* | |
H2A | 0.123 (4) | 0.346 (4) | 0.307 (3) | 0.064* | |
H5A | 0.190 (4) | 0.135 (4) | 0.798 (3) | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0362 (3) | 0.0295 (3) | 0.0316 (3) | 0.01035 (15) | 0.00732 (19) | 0.00466 (15) |
N5 | 0.0352 (9) | 0.0324 (9) | 0.0321 (9) | 0.0042 (7) | 0.0069 (7) | 0.0022 (7) |
N4 | 0.0377 (9) | 0.0340 (9) | 0.0347 (9) | 0.0083 (7) | 0.0068 (8) | 0.0038 (7) |
O3 | 0.0711 (12) | 0.0293 (8) | 0.0706 (12) | −0.0027 (8) | 0.0197 (10) | 0.0045 (8) |
N7 | 0.0518 (12) | 0.0323 (10) | 0.0403 (10) | −0.0068 (8) | 0.0041 (8) | 0.0013 (7) |
O1 | 0.0491 (10) | 0.0432 (10) | 0.0939 (15) | −0.0020 (8) | 0.0044 (10) | 0.0070 (10) |
C1 | 0.0423 (11) | 0.0329 (10) | 0.0338 (10) | 0.0117 (9) | 0.0103 (8) | 0.0042 (8) |
N1 | 0.0383 (9) | 0.0335 (9) | 0.0344 (9) | 0.0104 (7) | 0.0049 (7) | 0.0037 (7) |
O2 | 0.0666 (13) | 0.0423 (10) | 0.0904 (16) | −0.0113 (9) | −0.0318 (11) | −0.0032 (10) |
N6 | 0.0498 (11) | 0.0483 (11) | 0.0363 (10) | 0.0020 (9) | 0.0126 (8) | 0.0018 (9) |
N2 | 0.0469 (11) | 0.0328 (10) | 0.0576 (12) | 0.0049 (8) | −0.0053 (9) | 0.0004 (9) |
C4 | 0.0344 (11) | 0.0327 (10) | 0.0362 (11) | −0.0059 (8) | 0.0080 (9) | −0.0030 (8) |
C5 | 0.0554 (14) | 0.0444 (13) | 0.0514 (14) | 0.0156 (11) | 0.0244 (11) | 0.0008 (11) |
C6 | 0.0563 (15) | 0.0474 (13) | 0.0488 (13) | 0.0231 (12) | 0.0190 (11) | 0.0106 (11) |
C2 | 0.0482 (13) | 0.0395 (12) | 0.0437 (12) | 0.0166 (10) | −0.0001 (10) | 0.0048 (10) |
C3 | 0.0455 (14) | 0.0462 (14) | 0.0579 (15) | 0.0099 (11) | −0.0121 (12) | −0.0018 (11) |
N3 | 0.0438 (12) | 0.0467 (12) | 0.0680 (15) | 0.0033 (9) | 0.0055 (10) | 0.0122 (10) |
Cu1—N4 | 1.9748 (19) | N6—C4 | 1.369 (3) |
Cu1—N4i | 1.9748 (19) | N6—H6A | 0.87 (4) |
Cu1—N1 | 2.0331 (17) | N6—H6B | 0.88 (4) |
Cu1—N1i | 2.0332 (17) | N2—C3 | 1.334 (3) |
N5—N4 | 1.368 (3) | N2—H2 | 0.82 (4) |
N5—C4 | 1.343 (3) | C4—C5 | 1.375 (3) |
N5—H5 | 0.80 (4) | C5—C6 | 1.375 (4) |
N4—C6 | 1.332 (3) | C5—H5A | 0.88 (3) |
O3—N7 | 1.233 (3) | C6—H6 | 0.87 (4) |
N7—O1 | 1.247 (3) | C2—C3 | 1.358 (4) |
N7—O2 | 1.245 (3) | C2—H2A | 0.94 (4) |
C1—N1 | 1.340 (3) | C3—H3 | 1.03 (3) |
C1—C2 | 1.403 (3) | N3—H3A | 0.96 (4) |
C1—N3 | 1.347 (3) | N3—H3B | 0.96 (4) |
N1—N2 | 1.364 (3) | ||
N4—Cu1—N4i | 180.0 | H6A—N6—H6B | 116 (3) |
N4—Cu1—N1i | 91.01 (7) | N1—N2—H2 | 123 (3) |
N4—Cu1—N1 | 88.99 (7) | C3—N2—N1 | 111.0 (2) |
N4i—Cu1—N1 | 91.00 (7) | C3—N2—H2 | 126 (3) |
N4i—Cu1—N1i | 89.00 (7) | N5—C4—N6 | 121.9 (2) |
N1—Cu1—N1i | 180.0 | N5—C4—C5 | 106.7 (2) |
N4—N5—H5 | 120 (2) | N6—C4—C5 | 131.4 (2) |
C4—N5—N4 | 111.75 (18) | C4—C5—H5A | 127 (2) |
C4—N5—H5 | 128 (2) | C6—C5—C4 | 105.5 (2) |
N5—N4—Cu1 | 124.74 (14) | C6—C5—H5A | 127 (2) |
C6—N4—Cu1 | 130.97 (17) | N4—C6—C5 | 112.0 (2) |
C6—N4—N5 | 104.04 (19) | N4—C6—H6 | 120 (2) |
O3—N7—O1 | 120.1 (2) | C5—C6—H6 | 128 (2) |
O3—N7—O2 | 120.3 (2) | C1—C2—H2A | 125 (2) |
O2—N7—O1 | 119.5 (2) | C3—C2—C1 | 105.2 (2) |
N1—C1—C2 | 110.2 (2) | C3—C2—H2A | 129 (2) |
N1—C1—N3 | 122.1 (2) | N2—C3—C2 | 108.4 (2) |
N3—C1—C2 | 127.5 (2) | N2—C3—H3 | 123 (2) |
C1—N1—Cu1 | 135.03 (16) | C2—C3—H3 | 127.7 (19) |
C1—N1—N2 | 105.19 (18) | C1—N3—H3A | 111 (2) |
N2—N1—Cu1 | 119.06 (14) | C1—N3—H3B | 116 (2) |
C4—N6—H6A | 117 (2) | H3A—N3—H3B | 117 (3) |
C4—N6—H6B | 115 (2) | ||
Cu1—N4—C6—C5 | −173.70 (19) | N6—C4—C5—C6 | −176.8 (3) |
Cu1—N1—N2—C3 | 172.49 (18) | C4—N5—N4—Cu1 | 174.56 (15) |
N5—N4—C6—C5 | 0.5 (3) | C4—N5—N4—C6 | −0.1 (3) |
N5—C4—C5—C6 | 0.6 (3) | C4—C5—C6—N4 | −0.7 (3) |
N4—N5—C4—N6 | 177.4 (2) | C2—C1—N1—Cu1 | −170.29 (17) |
N4—N5—C4—C5 | −0.3 (3) | C2—C1—N1—N2 | −0.6 (2) |
C1—N1—N2—C3 | 0.8 (3) | N3—C1—N1—Cu1 | 14.0 (3) |
C1—C2—C3—N2 | 0.3 (3) | N3—C1—N1—N2 | −176.3 (2) |
N1—C1—C2—C3 | 0.2 (3) | N3—C1—C2—C3 | 175.6 (3) |
N1—N2—C3—C2 | −0.7 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3 | 0.96 (4) | 2.71 (3) | 3.495 (3) | 139 (3) |
N3—H3A···O2 | 0.96 (4) | 1.92 (4) | 2.849 (3) | 162 (3) |
N3—H3B···O3ii | 0.96 (4) | 2.20 (4) | 3.085 (3) | 153 (3) |
N6—H6A···O3iii | 0.87 (4) | 2.83 (3) | 3.480 (3) | 132 (3) |
N6—H6A···O1iii | 0.87 (4) | 2.22 (4) | 2.999 (3) | 149 (3) |
N6—H6B···O3iv | 0.88 (4) | 2.14 (4) | 3.019 (3) | 176 (3) |
N2—H2···N7i | 0.82 (4) | 2.60 (4) | 3.378 (3) | 159 (3) |
N2—H2···O1i | 0.82 (4) | 2.10 (4) | 2.908 (3) | 171 (4) |
N2—H2···O2i | 0.82 (4) | 2.40 (4) | 2.999 (3) | 131 (3) |
N5—H5···O1iii | 0.80 (4) | 2.47 (4) | 3.093 (3) | 136 (3) |
N5—H5···N3i | 0.80 (4) | 2.82 (4) | 3.462 (3) | 139 (3) |
C6—H6···N6v | 0.87 (4) | 2.70 (4) | 3.438 (3) | 143 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x−1/2, −y+1/2, z+1/2; (v) −x+1/2, y+1/2, −z+3/2. |
Acknowledgements
We are grateful to the Ministry of Education and Science of Ukraine for financial support.
Funding information
Funding for this research was provided by: Ministry of Education and Science of Ukraine (grant No. 22BF037-03; grant No. 22BF037-09).
References
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gamez, P., von Harras, J., Roubeau, O., Driessen, W. L. & Reedijk, J. (2001). Inorg. Chim. Acta, 324, 27–34. CrossRef CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Pérez, J. & Riera, L. (2009). Eur. J. Inorg. Chem. pp. 4913–4925. Google Scholar
Reedijk, J. (1987). Comprehensive Coordination Chemistry: The Synthesis, Reactions, Properties and Applications of Coordination Compounds, Vol. 2, edited by G. Wilkinson, R. D. Gillard & J. A. McCleverty. Oxford: Pergamon Press. Google Scholar
Rigaku OD (2023). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Ruan, B.-F., Liang, Y.-K., Liu, W.-D., Wu, J.-Y. & Tian, Y.-P. (2012). J. Coord. Chem. 65, 2127–2134. CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Świtlicka-Olszewska, A., Machura, B., Mroziński, J., Kalińska, B., Kruszynski, R. & Penkala, M. (2014). New J. Chem. 38, 1611–1626. Google Scholar
Titi, A., Zaidi, K., Alzahrani, A. Y. A., El Kodadi, M., Yousfi, E. B., Moliterni, A., Hammouti, B., Touzani, R. & Abboud, M. (2023). Catalysts 13, 162. CrossRef Google Scholar
Wang, Y.-F., Li, Z., Sun, Y.-C. & Zhao, J.-S. (2014). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 44, 277–281. Web of Science CSD CrossRef CAS Google Scholar
Zaimović, M. Š., Kosović Perutović, M., Jelušić, G., Radović, A. & Jaćimović, Ž. (2022). Front. Pharmacol. 13. https://doi. org/10.3389/fphar. 2022.921157. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.