1

Inorganic Chemistry Research

Article

Synthesis, Crystallography, and Antibacterial Activity of a

New Cocrystal Copper-Cerium Based on 1,10-
Phenanthroline
Niloufar Dorostia,*, Maryam Passa and Daniel Fuhrmannb
a
Faculty of Chemistry, Lorestan University, Khorram Abad, Iran
b
Department of Chemistry and Mineralogy, Institute of Inorganic Chemistry, University of Leipzig, Leipzig, Germany

Received: August 2, 2023; Accepted: September 10, 2023

Cite This: Inorg. Chem. Res. 2023, 7-13. DOI: 10.22036/j10.22036.2023.409813.1150
Abstract: The cocrystal Copper-Cerium based on 1,10-phenanthroline,
[Cu(Phen)3][Ce(Phen)(NO3)5] (C), was synthesized by condensation of
Ce(NO3)3.6H2O, Cu(ClO4)2, and 1,10- phenanthroline in ethanol solution.
Newly synthesized cocrystal was characterized by FT-IR, UV-Vis, and
elemental analysis. The crystal structure of C was determined by X-ray
crystallography. Antibacterial activity of compounds was evaluated against
two gram-positive S. aureus, S. saprophyticus and one gram-negative P.
aeruginosa bacteria, by the disk-diffusion method. The antibacterial
efficacy of the compounds in the concentration range of 10-40 μg/D is
demonstrated by determining the inhibition zone.

Keywords: Cocrystal, X-ray structure, Antibacterial, Hirshfeld analysis

1. INTRODUCTION
Considerable efforts have been devoted to the design and ligands, 1,10-phenanthroline (Phen) and its derivatives are
synthesis of cocrystals, in other words crystals composed the subjects of special attention in ternary lanthanide
of two or more distinct molecules in a crystalline lattice, complexes.28-33 1,10-Phenanthroline is a biologically
owing to their importance in the pharmaceutical important ligand, and some of its metal complexes
industry.1-3 These compounds show great potential in exhibit effective activityagainst various strains of
serving as new antitumor agents.4,5 The coordination microorganisms.34,35 In this study, the novel cocrystal
mode and orientation of the donor groups of organic Copper-Cerium (C) based on 1,10-phenanthroline, was
ligands play an important role in controlling coordination synthesized by condensation of Ce(NO3)3.6H2O,
compound structures.6 Copper(II) chelates have been Cu(ClO4), and 1,10- phenanthroline in ethanol solvent.
found to interact with biological systems and exhibit The resultant Cocrystal was identified via IR
antineoplastic, antibacterial, antifungal, and anticancer spectroscopy, elemental analysis, and X-ray
activity.7-14 Some Cu(II) N/S, O/N, and N-donor chelators Crystallography. In addition, the antimicrobial activity
are good anticancer agents due to their strong binding against S. aureus, S. saprophyticus, and P. aeruginosa,
ability with DNA base pairs.15-20 Lanthanide complexes was studied by the disk-diffusion method.
are widely used as optical and magnetic materials,
catalysts, and useful in biomedicine.21-24 Besides, it is well 2. EXPERIMENTAL
known that lanthanides behave as typical hard acids and Materials and physical methods
prefer donor atoms with the preference O > N > S and F > All chemicals and solvents such as 1,10-phenanthroline,
Cl.21 An overview of the literature shows a wide range of Ce(NO3)3.6H2O, Cu(ClO4)2, acetonitrile, methanol, and ethanol
antibacterial activity of Cerium(III) compounds.25,26 were of reagent grade and obtained without further purification.
Infrared (IR) spectra were recorded on a Shimadzu FT-IR 8400S
The cream or aqueous solution of Ce compounds has been (Japan) in the range 400-4000 cm_1 using KBr pellets. Melting
widely used in the antibacterial treatment of burn wounds. points were measured on an Electrothermal 9100 apparatus.
Cerium materials cannot penetrate the cell membrane of Electronic spectra were recorded by Varian, Cary 100 UV-Vis
mammals and no toxicity has been observed with Ce.27 A spectrophotometer in the range of 200-800 nm.
literature survey reveals that among the different neutral
Inorganic Chemistry Research Article

X-Ray structure analysis the compound indicate that nitrogen atoms of the Phen
Single-crystal X-ray diffraction measurements were carried out group participate in coordination with the Ce(III) ion
on a STOE IPDS 2T image plate diffractometer system equipped (Figure 1).40
with a sealed Mo X-ray tube and a graphite monochromator
crystal (λ(MoKα) = 71.073 pm). Data reduction and numerical
absorption correction were carried out with STOE X-AREA
software.36 All structures were solved by direct methods using
SHELXS-2018 and refined with SHELXL-2018 37 using
WinGX38 as a graphical frontend. CCDC 2285429 contains
the supplementary crystallographic data for this paper. This
data can be obtained free of charge via
http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the
CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44
1223 336033; E-mail: deposit@ccdc.cam.ac.uk).

Antimicrobial Test
The compounds were dissolved in DMSO at the concentration of
1000, 500, and 100 µg/mL and used for antibacterial evaluation.
The solution was UV-sterilized and used for disk diffusion.
Paper discs (6.5 mm) were impregnated with 40 µL of the
sample and the solvent was evaporated under a safety cabinet at
room temperature. The bacterial suspension's turbidity was
compared and equalized with the Mac-Farland 0.5 standard. Figure 1. FT-IR spectrum of (a) Phen, and (b) cocrystal C.
Then, the suspension was spread over a Muller Hinton agar plate
with sterile swab. The plates were incubated at 35 oC overnight Ultraviolet spectra
and the inhibition zone (IZ) was measured. The antibacterial UV spectra of the Phen and cocrystal C are depicted in
effect of C, Phen, and metal salts by using the disk diffusion DMSO solution (1.0 × 10-5 mol/L) in the wavelength
method at 10, 20, and 40 µg/D (microgram per paper discs) range of 200–400 nm. The C and Phen have strong π→π*
concentrations was investigated against two bacteria (S. aureus, transition absorption. The maximum absorption band at
S.saprophyticus) and one gram-negative bacterium 266 nm for the cocrystal C is similar to that in the Phen,
(P.aeruginosa). DMSO solvent as a negative control and
which indicates that the formation of Ce-N has no
antibiotics Gentamicin and Vancomycin as positive control were
considered that microbial shadow created around the disks is the conspicuous influence on the UV absorption of the Phen.
indicative antibacterial effect of compounds. By changing the solvent to ethanol, the absorption
spectrum of Phen and C exhibit two relatively strong
Synthesis of [Cu(Phen)3][Ce(Phen)(NO3)5] (C) absorption peaks at 230 and 266 nm, which can be
To a solution of 1,10-phenanthroline (Phen) (0.5 mmol, 0.090 g) assigned to the π→π* transition of the Phen ring
in 10 mL acetonitrile, Ce(NO3)3.6H2O (0.25 mmol, 0.108 g) and (Figure 2).
Cu(ClO4)2(0.25 mmol, 0.092g) in methanolic solution was The solvatochromic behavior of cocrystal C is the shift of
added and the resulting mixture was then stirred 72h at room the π→π* band wavelength due to the presence of solvent
temperature. Green single crystals were obtained by with different polarity and interaction between the solute
recrystallization from ethanol solution at room temperature.
and solvent molecules.
Yield 30%, M.p. 229–230 °C; Anal. Calc. for
C48H32CeCuN13O15: C, 46.69; H, 2.61; N, 14.74%. Found: C,
46.75; H, 2.65; N, 14.68%. IR (KBr, cm−1): 3070 (s), 1620 (s),
1585 (s), 1442 (w), 1334 (w), 1218 (s), 1141 (s), 1099 (s), 1037
(s), 848 (s), 725 (s), 636 (s). UV–Vis in DMSO: λmax 266 nm.

3. RESULTS AND DISCUSSION

Infrared-Spectra
In the IR spectra of Phen, the absorption bands at
1571 cm−1 and 1496 cm−1 were assigned to ν(C=N) and
ν(C=C) stretching vibrations, respectively. These bands
shifted to lower wavenumber 1512 cm−1 and 1438 cm−1 in
the IR spectra of C, which indicate the nitrogen atoms of
Phen are coordinated to Ce(III) ion and Cu(II). In
addition, the bands at 429 cm−1 and 505 cm-1 were Figure 2. UV-Vis spectra in (a) C, and (b) Phen in (1) DMSO and (2)
assigned to ν(Cu–Nphen) in the cocrystal.39 Meanwhile, the Ethanol.
new bands occurring in the region 420 cm−1 ν(Ce−N) for

Inorg. Chem. Res. 2023, 7, 7-13

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 Inorganic Chemistry Research Article

Description of the molecular structure of cocrystal (C) other reported compounds.8 In the asymmetric unit of
Green crystals of (C) were obtained after slow [Ce(Phen)(NO3)5]2-, the central Ce ion is 12-coordinated,
evaporation at room temperature (see Experimental
section). Crystallographic data and details of the X-ray
analysis are given in Table 1, and the defined dihedral
angles and distances of (C) are summarized in Table 2.

Table 1. Crystallographic and Structural Refinement Data for

CocrystalC
Formula C48H32CeCuN13O15
Formula weight 1234.52
Temperature (K) 200 K
Wavelength λ (Å) 0.71073
Crystal system orthorhombic
Space group P 2 1 21 21
Crystal size (mm3) 0.438 × 0.346 × 0.267
a (Å) 12.4494(4)
b (Å) 17.9555(5)
c (Å) 22.6236(9)
α (º) 90
β (º) 90
γ (º) 90
Volume (Å3) 5057.2(3)
Z 4
Density (calcd.) (g cm-1) 1.621
F(000) 2472.0
Absorption coefficient (mm-1) 1.39
Index ranges h, k, l max -15 ≤ h ≤ 15, -22 ≤ k ≤ 22, -25 ≤ l ≤ 27
2Θ range for data collection/° 3.6 to 52 Figure 3. Side view of the crystal packing of C in the bc-plane.
Unique data (Rint) 9913
Parameters, restrains 703, 0
Final R indexes [I> = 2σ (I)] R1 = 0.0518, wR2 = 0.1307
Final R indexes [all data] R1 = 0.0653, wR2 = 0.1402
Goodness of fit on F2 (S) 1.029
Largest diff peak and hole (e Å-3) 0.96/-1.86

Table 2. Selected bond lengths (Å) and angles (˚) in C

Bond lengths (Å) Bond angles (˚)
Cu1-N3 2.027 Ce1-O9 2.702 N3-Cu1-N4 80.77
Cu1-N4 2.090 Ce1-O10 2.618 N5-Cu1-N6 75.97
Cu1-N5 2.090 Ce1-O11 2.689 N7-Cu1-N8 77.53
Cu1-N6 2.326 Ce1-O13 2.627 N1-Ce1-N2 60.87
Cu1-N7 2.276 Ce1-O15 2.672 O1-Ce1-O2 47.87
Cu1-N8 2.032 O1-N9 1.285 O4-Ce1-O5 47.79
Ce1- N1 2.722 O2-N9 1.246 O7-Ce1-O8 48.56
Ce1-N2 2.764 O4-N10 1.270 O10-Ce1-O11 47.77
Ce1-O1 2.605 O5-N10 1.257 O13-Ce1-O15 48.56
Ce1-O2 2.709 O11-N12 1.278
Ce1-O4 2.610 O10-N12 1.240
Ce1-O5 2.737 O15-N13 1.282
Ce1-O8 2.537 O13-N13 1.266
O14-H14 2.508 O13-C36 2.707
O14-C48 3.007 N11-C35 2.879
O14-C47 3.090

X-ray analysis showed that C crystallizes in the

orthorhombic system P212121with four discrete molecules
in the unit cell (Figure 3).
Figure 4. A view of the asymmetric unit and atom-labelling scheme
The asymmetric unit of (C) contains two symmetry- for[Cu(Phen)3]2+[Ce(Phen)(NO3)5]2-.
independent pairs of [Cu(Phen)3]2+ and
[Ce(Phen)(NO3)5]2- (Figure 4). made up of two nitrogen atoms of Phen and ten oxygen
Three molecules of Phen are coordinated to the copper(II) atoms from five nitrate counter ions; d (Ce-O) = 2.537(6)
ion in a bidentate manner at the nitrogen site of the - 2.737(7) Å and d (Ce-N) = 2.722(8) - 2.764(8) Å
molecules, and one Phen is attached at the Ce atom. Six- (Table 2 and Figure 4).41
coordinated Cu(II) metal ion has a distorted octahedral Non-covalent interactions as weak hydrogen bonds
geometry (Figure 5). The Cu-N bond lengths lie in the comprising CHphen…Onitro (C(36)–H(36)…O(13): d(C36–
range 2.027(7)–2.326(9) Å in good consonance with the O13) = 3.623(1) Å, θ(C36–H36…O13) = 162.10(9)°),

Inorg. Chem. Res. 2023, 7, 7-13

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Inorganic Chemistry Research Article

(C(24)–H(24)…O(14): d(C24–O14) = 3.623(1) Å,

θ(C24–H24…O14) = 162.10(9)°), (C(19)–H(19)…O(6):
d(C19–O6) = 3.623(1) Å, θ(C19–H19…O6) =
162.10(9)°) (between hydrogens of Phen and Onitro) lead
to a two dimensional framework (Figure 5a).
Besides, two neighboring chains are correlated by π-π
stacking interactions between aromatic rings of Phen
groups (shown in Figure 5b) with centroid–centroid
distance of 3.769 Å and an angle of 10.48˚ between two
planes. There are also weak intramolecular hydrogen
bonds between Nnitro...CHphen (Figure 5c). Eventually, C
adopts a 3D supramolecular structure (Figure 5d). Figure 6. Hirshfeld surfaces mapped with (a) dnorm and (b)shape
index of C.

Furthermore, 2D fingerprint plots (FPs), derived from the

HS, are generated for visualizing percentage contribution
of each contact, providing a ‘fingerprint’ of the different
intermolecular interactions throughout the structure.
Figure 7 shows the overlap of all contact type over the HS
of the cocrystal, in which the markedblue color region and
length of spikes are indicative of the strength of contacts
present in crystalpacking. The H···H interactions in
Figure 6 are found to be located in the middle of scattered
points in the FP and have the (contributions 24.1%) over
the total HS as the surface is wrapped in a large number
of H atoms. Figure 6shows that O···H contact, and N-H
intermolecular interactions, appears as two sharp long
spikes in the FPs. Other contacts, such as C···H, O···C,
N···H, and C···C interactions respectively having 20.5%,
4%, 3.8%, and 7.2% are observed. It is clear from the
above analysis that the isotropic van der Waals, strong
O···H, and weak C···H interactions play major roles in
crystal packing.43
percentages of contacts contributed to the totalHirshfeld
Figure 5. Crystal packing of [Cu(Phen)3]2+[Ce(Phen)(NO3)5]2-. (a) A surface area of C. de and di refer to distances from the
view of short contacts CH…O and CH…N interactions. (b) π-π stacking
interactions of the obtained crystal; (c) Side view of intramolecular
surface to the nearest nucleus exterior and interior to the
interaction in C, (d) Representation of interactions in C, resulting in 3D surface, respectively.
arrangements.
Antibacterial activity
Hirshfeld analysis The cocrystal C, Phen, Ce(NO3)3.6H2O, and Cu(ClO4)2
Hirshfeld surfaces and molecular fingerprints for were screened for in vitro antibacterial activities against
cocrystal C was prepared using Crystal-Explorer 3.1, and P.aeruginosa, S. aureus, and S.saprophyticus by disc
is presented in Figure 6. Hirshfeld surface analysis is a diffusion method, and the values of C, Phen, and metal
powerful tool for visualizing and understanding of salts are listed in Table 3 and Figure 8. According to the
intermolecular interactions.42 The contribution percentage results, all components have activity against P.
of different interactions to the Hirshfeld surface area is aeruginosa bacterium, resulting in stronger C activity
shown in Figure 7. The Hirshfeld surface (HS) mapped against the titled bacterium compared to the other two
with the dnorm value of the cocrystal displays the area bacteria. Besides, the C has significant activities against
encoded with different colors, in which the red regions all the bacteria than Phen and metal salts. This cocrystal
represent the close contacts formed. In contrast, the white- has potent activity against S. aureus and S.saprophyticus,
colored regionscorrespond to weak contacts and the blue- similar to Vancomycin. The obtained data show that Phen
colored areas are considered to be absent of is not a biologically active, but its cocrystal with two
importantcontacts. Herein, the red areas where the metal ions Cu(II) and Ce(III) show significantly enhanced
distance between adjacent atoms is shorter than the sum activity against bacteria. Previous reports in the literature
of the van der Waals radii deserve to be highlighted. suggest that the MICs of the La(III) complex are two to

Inorg. Chem. Res. 2023, 7, 7-13

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Inorganic Chemistry Research Article

Figure 7. 2D fingerprint plots, full and resolved into O...H, H…H, C...H, C..C, C...O and N...H contacts, showing.

Figure 8. Antibacterial activity of Phen, Cu(ClO4)2, Ce(NO3)3.6H2O, and cocrystal C.

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Inorganic Chemistry Research Article

Table 3. In vitroantibacterial results of Phen, Cu(ClO4)2, Ce(NO3)3.6H2O, and cocrystal C

Inhibition zone in mm
Compound
concentration µg/D S. aureus S. saprophyticus P. aeruginosa
10 - - -
Phen 20 - - 15
40 15 - 20
10 - - -
Cu(ClO4)2 20 - - -
40 - - 8
10 - - -
Ce(NO3)3.6H2O 20 - - -
40 - - 10
10 - - -
C 20 11 15 15
40 14 18 20
Vancomycin 10 21 15 -
Gentamicin 30 - - 25

three orders of magnitude smaller than those of the phen therapeutic agents.
and the lanthanum salt (La(NO3)3·6H2O). The results
suggest that the La(III) complex has strong antibacterial ACKNOWLEDGMENTS
activity against gram-positive and gram-negative bacteria, The authors would like to acknowledge the financial
implying that the La(III) complex may become a broad- support of Lorestan University for this research under
spectrum antibacterial agent.44 grant number 1401-4-05-3-20-1403.
There are specific reports of Cu(II) complexes where the
presence of the copper ion appears to enhance the AUTHOR INFORMATION
antimicrobial properties of ligand.45 Corresponding Author
The biological activity of metal compounds may be Niloufar Dorosti: Email: nilufardorosti@gmail.com,
explained based on the effect of metal ion on the cell ORCID: 0000-0003-3822-8214
metabolism.8 The antimicrobial activity of C will increase
along with the rise of their concentration in the range of Author(s)
10–40 µg/D. In contrast, the antimicrobial activity for Maryam Pass, Daniel Fuhrmann
metal salts in the same concentrations is low. The
simultaneous presence of Phen, Cu(II), and Ce(III) in
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