Diaqua­dichloridobis[quinazolin-4(1H)-one-κN 3]copper(II)

Kambarali Turgunov; Shirin Shomurotova; Nasir Mukhamedov; Bakhodir Tashkhodjaev

doi:10.1107/S1600536810048890

. 2010 Nov 27;66(Pt 12):m1680. doi: 10.1107/S1600536810048890

Diaquadichloridobis[quinazolin-4(1H)-one-κN ³]copper(II)

Kambarali Turgunov ^a,^*, Shirin Shomurotova ^b, Nasir Mukhamedov ^a, Bakhodir Tashkhodjaev ^a

PMCID: PMC3011606 PMID: 21589337

Abstract

In the title complex, [CuCl₂(C₈H₆N₂O)₂(H₂O)₂], the Cu^II ion is located on an inversion center and is octahedrally coordinated by two N atoms of the 1H-quinazolin-4-one ligand, two chloride ligands and two aqua ligands. The axial Cu—O distances are significantly longer [2.512 (2) Å], than the Cu—N [2.022 (2) Å] and Cu—Cl [2.3232 (4) Å] distances as a result of Jahn–Teller distortion. Aqua ligands are involved in intra- and intermolecular hydrogen bonding, and N—H⋯O intermolecular hydrogen bonds are formed between the organic ligands. In addition, weak π–π interactions are observed between the benzene rings of the ligand [centroid–centroid distance = 3.678 (1) Å].

Related literature

The crystal structure of pyrimidin-4(3H)-one was reported by Vaillancourt et al. (1998 ▶). For a Cd(II) coordination polymer with quinazolin-4(3H)-one, see: Turgunov & Englert (2010 ▶). For computational studies of quinazolin-4-one derivatives, see: Bakalova et al. (2004 ▶).

Experimental

Crystal data

[CuCl₂(C₈H₆N₂O)₂(H₂O)₂]
M _r = 462.77
Monoclinic,
a = 6.7438 (3) Å
b = 18.5328 (8) Å
c = 6.7831 (3) Å
β = 90.735 (3)°
V = 847.69 (6) Å³
Z = 2
Cu Kα radiation
μ = 5.03 mm⁻¹
T = 293 K
0.55 × 0.35 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T _min = 0.366, T _max = 1.000
5548 measured reflections
1725 independent reflections
1639 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.089
S = 1.10
1725 reflections
137 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1998 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048890/nk2075sup1.cif

e-66-m1680-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048890/nk2075Isup2.hkl

e-66-m1680-Isup2.hkl^{(85KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1ⁱ	0.84 (2)	1.92 (3)	2.732 (2)	162 (3)
O1W—H2W⋯Cl1ⁱⁱ	0.85 (2)	2.51 (2)	3.355 (2)	171 (4)
N1—H1⋯O1ⁱⁱⁱ	0.84 (2)	2.39 (3)	3.022 (2)	133 (3)
N1—H1⋯Cl1^iv	0.84 (2)	2.63 (3)	3.324 (2)	140 (3)
C2—H2A⋯O1W	0.93	2.38	2.972 (3)	121
C7—H7A⋯O1W^v	0.93	2.57	3.421 (3)	152

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F3–T045).

supplementary crystallographic information

Comment

In solutions, 4-quinazolinone could have in principle three isomers—1H, 3H, and 4-OH, as shown in Figure 1, with preference of 3H-tautomer. Recently, the crystal structure of a Cd^II coordination complex has been reported, in which 3H-quinazolin-4-one (3H-tautomer) acted as a ligand (Turgunov & Englert, 2010). We now report the structure of a Cu^II complex in which 1H-quinazolin-4-one (1H-tautomer) acts as a ligand.

In the title compound, Cu^II ion is located on the inversion center and has an octahedral coordination environment: two ligands coordinated via N atoms in position 3, two chloride ligands and two aqua ligands (Figure 2). The distances between Cu and coordination atoms are the following: d(Cu—N3) = 2.022 (2) Å, d(Cu—Cl) = 2.3232 (4) Å and d(Cu—Ow) = 2.512 (2) Å. Long distances of metal-aqua bonds than other four coordination bonds indicate existence of the Jahn-Teller elongation effect.

Aqua ligands are involved in intramolecular and intermolecular hydrogen bonding. Intramoleculer H-bonding is occurring with carbonyl group of the ligand. An intermolecular H-bonding of aqua and chloride ligands gives raise to chains along [001] (Figure 3). In addition, between ligand and water molecules are formed weak C–H···O hydrogen bonds. Intermolecular N—H···O and N—H···Cl hydrogen bonds formed between the organic and chloride ligands link molecular complexes into hydrogen-bonded chains along [100] (Figure 4; Table 1). Weak π···π ring interactions connect the molecular complexes along [010] and [001] directions. [Cg1···Cg1^vi=3.678 (1) Å, where Cg1=C4A–C5–C6–C7–C8–C8A; ^vi = x, 3/2 - y, 1/2 + z].

Experimental

A solution of 17.05 mg (0.1 mmol) of copper(II) chloride dihydrate in 2 ml of water was added to a solution of 29.23 mg (0.2 mmol) of 3H-quinazolin-4-one in 5 ml of ethanol. The solution allowed to stand at room temperature for one week, after which light-blue crystals were obtained.