Doxofyllinium tetra­chloridoanti­monate(III) monohydrate

Wan Xing Wei; Wen-Jie Feng; Bo-Jiöng Zheng; Ying Chen; Zhi-Min Jin

doi:10.1107/S1600536807065774

. 2007 Dec 12;64(Pt 1):m167. doi: 10.1107/S1600536807065774

Doxofyllinium tetrachloridoantimonate(III) monohydrate

Wan Xing Wei ^a, Wen-Jie Feng ^b, Bo-Jiöng Zheng ^c, Ying Chen ^b, Zhi-Min Jin ^b,^*

PMCID: PMC2915103 PMID: 21200515

Abstract

The title compound, (C₁₁H₁₄N₄O₄)[SbCl₄]·H₂O, comprises a protonated doxofyllinium cation [7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-2,6-dioxo-3,7-dihydro-1H-purin-9-ium], an [SbCl₄]⁻ anion and a water molecule linked by N—H⋯O and O—H⋯Cl hydrogen bonds: the [SbCl₄]⁻ anions form centrosymmetric dimers via weak Sb⋯Cl interactions [Sb⋯Cl = 3.1159 (9) Å]. The geometrical arrangement in the crystal structure is characterized by slipped π–π stacking of the parallel purine ring systems, with an interplanar separation of 3.32 Å.

Related literature

For related literature, see: Chen, Tu, Shu et al. (2007 ▶); Chen, Tu & Jin (2007 ▶);Feng et al. (2007 ▶); Franzone et al. (1981 ▶, 1989 ▶); Villani et al. (1997 ▶); Zhao & Li (2001 ▶).

Experimental

Crystal data

(C₁₁H₁₄N₄O₄)[SbCl₄]·H₂O
M _r = 548.85
Triclinic,
a = 8.9783 (5) Å
b = 10.4727 (5) Å
c = 11.0357 (4) Å
α = 68.7550 (10)°
β = 82.671 (2)°
γ = 88.228 (2)°
V = 959.10 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.03 mm⁻¹
T = 153 (2) K
0.33 × 0.28 × 0.27 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.459, T _max = 0.486 (expected range = 0.547–0.579)
9490 measured reflections
4399 independent reflections
4151 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.097
S = 1.05
4399 reflections
236 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.40 e Å⁻³
Δρ_min = −2.97 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065774/gg2051sup1.cif

e-64-0m167-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065774/gg2051Isup2.hkl

e-64-0m167-Isup2.hkl^{(209.1KB, 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
N1—H1⋯O5	0.92 (4)	1.75 (4)	2.663 (4)	172 (4)
O5—H5C⋯Cl1	0.81 (3)	2.65 (2)	3.332 (3)	142 (2)
O5—H5D⋯Cl1ⁱ	0.81 (3)	2.41 (2)	3.205 (3)	166 (5)
C3—H3A⋯O1	0.97	2.45	3.145 (8)	128
C7—H7⋯Cl3ⁱⁱ	0.93	2.56	3.432 (3)	157

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

supplementary crystallographic information

Comment

Doxofylline [7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione] is a therapeutic agent with anti-asthmatic (Franzone et al., 1989), anti-inflammatory activities (Zhao et al., 2001) and a bronchodilating effect on smooth muscle (Franzone et al., 1981; Villani et al., 1997). So far several organic compounds containing doxofylline have been synthesized (Chen, Tu, Shu et al.,2007); Chen, Tu & Jin, 2007; Feng et al., 2007), but the doxofylline complex containing metal has not been reported. All of the above studies provide important references to futher research into doxofylline. Herein we present here the structure of the title compound (Scheme 1), (I).

As depicted in Fig. 1, the compound (I) is comprised of a doxofylline cation, a SbCl₄ anion and a water molecule. The N1 of doxofylline is protonated and links to the water molecule by N1—H1···O5 hydrogen bond, and the water molecule links the SbCl₄ anion by O5—H5C···Cl interactions. The dihedral angle between the plane of the purine ring and the approximate plane through C4/O3/C6/O4 is 68.5°. The pure compound is 8.42° (Chen, Tu, Shu et al.,2007); Chen, Tu & Jin, 2007). In the purine ring, the bond length of N4—C11 [1.392 (3) Å] bond is somewhat longer than the corresponding N—C [1.374 (4) Å] bond length in the Chen's case (Chen et al., 2007).

The symmetrically related SbCl₄ link into dimers via coordinated bonds of Sb1—Cl4 (-x + 1, -y + 2, -z + 2) [3.1159 (9) Å] (Fig. 2), which plays an important role in the formation of the crystal. In addition, there exists slipped π···π stacking between symmetrically related pyridines rings at (-x + 2, -y + 1, -z + 1), with a centroid to centroid distance equal to be 3.662 (6) Å. With intermolecular hydrogen bonds listed in Table 1, the stacking interactons further stabilize the crystal structure (Fig. 3).

Experimental

Antimony trichloride, hydrochloride acid and doxofylline in a 1:1:1 molar ratio were mixed and dissolved in sufficient acetone by heating to a temperature at which a clear solution resulted. Crystals of (I) were formed by gradual evaporation of acetone over a period of three days at 298 K.