trans-Dichloridobis{2-chloro-6-[(3-fluoro­benz­yl)amino]-9-isopropyl-9H-purine-κN 7}platinum(II)

Zdeněk Trávníček; Pavel Štarha

doi:10.1107/S1600536813013202

. 2013 May 18;69(Pt 6):m331. doi: 10.1107/S1600536813013202

trans-Dichloridobis{2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine-κN ⁷}platinum(II)

Zdeněk Trávníček ^a,^*, Pavel Štarha ^a

PMCID: PMC3684891 PMID: 23794993

Abstract

In the title compound, trans-[PtCl₂(C₁₅H₁₅ClFN₅)₂], the Pt^II atom, located on an inversion centre, is coordinated by the purine N atoms of the 2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine ligands and two Cl atoms in a slightly distorted trans-square-planar coordination geometry [N—Pt—Cl angles = 89.91 (5) and 90.09 (5)°]. Weak intramolecular N—H⋯Cl contacts occur. In the crystal, C—H⋯Cl and C—H⋯F contacts, as well as weak π–π stacking interactions [centroid–centroid distances = 3.5000 (11) and 3.6495 (12) Å] connect the molecules into a three-dimensional architecture.

Related literature

For the structures of platinum(II) dichlorido complexes involving different 2-chloro-6-[(substituted-benzyl)amino]-9-isopropyl-9H-purine derivatives, see: Trávníček et al. (2006 ▶); Szüčová et al. (2008 ▶). For the synthesis of 2-chloro-6-[(substituted-benzyl)amino]-9-isopropyl-9H-purine derivatives, see: Štarha et al. (2009 ▶).

Experimental

Crystal data

[PtCl₂(C₁₅H₁₅ClFN₅)₂]
M _r = 905.53
Monoclinic,
a = 9.37786 (13) Å
b = 12.86530 (17) Å
c = 14.2891 (2) Å
β = 107.9165 (16)°
V = 1640.36 (4) Å³
Z = 2
Mo Kα radiation
μ = 4.65 mm⁻¹
T = 105 K
0.35 × 0.35 × 0.35 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.293, T _max = 0.293
13582 measured reflections
2881 independent reflections
2726 reflections with I > 2σ(I)
R _int = 0.010

Refinement

R[F ² > 2σ(F ²)] = 0.015
wR(F ²) = 0.037
S = 1.10
2881 reflections
216 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(17.7KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013202/jj2166sup1.cif

e-69-0m331-sup1.cif^{(17.7KB, cif)}

Click here for additional data file.^{(141.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013202/jj2166Isup2.hkl

e-69-0m331-Isup2.hkl^{(141.4KB, 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
N6—H6A⋯Cl2ⁱ	0.88	2.53	3.222 (2)	136
C13—H13A⋯Cl2ⁱⁱ	0.95	2.86	3.492 (2)	125
C18—H18A⋯F1ⁱⁱⁱ	0.98	2.49	3.450 (3)	166

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

Acknowledgments

This work was supported by Palacký University (grant No. PrF_2013_015). The authors wish to thank Mr Tomáš Šilha for performing the CHN elemental analysis.

supplementary crystallographic information

Comment

In the title compound, the Pt^II atom is located on an inversion centre and thus, the asymmetric unit contains one-half of the described platinum(II) complex (Fig. 1). The central Pt^II atom is four-coordinated by two chloride anions [Pt—Cl = 2.2940 (5) Å] and two 2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine molecules [Pt—N = 2.011 (2) Å], which are bonded to platinum through their N7 atoms of the purine moieties. The geometry of the complex is slightly distorted square-planar with the N—Pt—Cl angles in the vicinity of the central metal atom of 89.91 (5)° and 90.09 (5)°, and the mean plane fitted through the PtCl₂N₂ unit (r.m.s. deviation = 0.000 Å) being planar. Both the essentially planar purine moieties [with the maximum deviation of 0.050 (2) Å for the C5 atom] are mutually coplanar and each of them forms the dihedral angle of 62.04 (3)° and 49.58 (5)° with the PtCl₂N₂ unit, and the benzene ring, respectively (Fig. 1). The molecular structure involves weak N6—H6A···Cl2 intramolecular interactions (Table 1, Fig. 1). In the crystal, the molecules are connected together through weak C13—H13A···Cl2, C18—H18A···F1 and π···π (between the six-membered pyrimidine and benzene rings) intermolecular interactions into a three-dimensional architecture (Fig. 2 and 3, Table 1).

Experimental

The solution of 2-chloro-6-[(3-fluorobenzyl)amino]-9-isopropyl-9H-purine (0.5 mmol; prepared according to the previously described procedure, (Štarha et al., 2009) in acetone (10 ml) was slowly poured into the distilled water solution of K₂PtCl₄ (0.25 mmol). The reaction mixture was stirred at laboratory temperature, until the initial orange colour turned to yellow. The solid was collected by filtration and washed with distilled water and acetone. Part of the product was recrystallized from N,N`-dimethylformamide. The crystals suitable for a single-crystal X-ray analysis formed after two weeks. Analysis calculated for C₃₀H₃₀N₁₀Cl₄F₂Pt₁: C 39.8, H 3.3, N 15.5%; found: C 39.9, H 3.3, N 15.3%. Elemental analysis (C, H, N) was performed on a Thermo Scientific Flash 2000 CHNO-S Analyzer.