3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetra­hydro-4H-thio­pyrano[3′,4′:2,3]thieno[5,4-d]pyrimidin-4-one

Hai Xie; Shuang-Ming Meng; Yue-Qin Fan; Yong Guo

doi:10.1107/S1600536808038683

. 2008 Nov 26;64(Pt 12):o2434. doi: 10.1107/S1600536808038683

3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetrahydro-4H-thiopyrano[3′,4′:2,3]thieno[5,4-d]pyrimidin-4-one

Hai Xie ^a,^*, Shuang-Ming Meng ^a, Yue-Qin Fan ^a, Yong Guo ^a

PMCID: PMC2959906 PMID: 21581402

Abstract

In the title compound, C₂₀H₂₁N₃OS₂, the piperidinyl ring has a distorted chair conformation. Weak intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing exhibits short intermolecular S⋯S distances of 3.590 (2) Å.

Related literature

For properties of the compounds containing th thienopyrimidine system, see: Muller et al. (2002 ▶); Chambhare et al. (2003 ▶). For related crystal structures, see: Hu et al. (2007 ▶); Xie et al. (2007 ▶).

Experimental

Crystal data

C₂₀H₂₁N₃OS₂
M _r = 383.52
Triclinic,
a = 9.851 (2) Å
b = 10.755 (3) Å
c = 10.864 (3) Å
α = 117.573 (4)°
β = 106.099 (4)°
γ = 97.322 (4)°
V = 935.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 (2) K
0.26 × 0.12 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.926, T _max = 0.982
4908 measured reflections
3203 independent reflections
2739 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.146
S = 1.08
3203 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038683/cv2480sup1.cif

e-64-o2434-sup1.cif^{(21.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038683/cv2480Isup2.hkl

e-64-o2434-Isup2.hkl^{(157.1KB, 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
C7—H7B⋯O1ⁱ	0.97	2.56	3.321 (5)	136

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Symmetry code: (i) Inline graphic .

Acknowledgments

We gratefully acknowledge financial support of this work by a key grant (No. 2008K1) from the Shanxi Datong University Foundation of Shanxi Province.

supplementary crystallographic information

Comment

The derivatives of heterocycles containing the thienopyrimidine system have proved to show significant antifungal, antibacterical, anticonvulsant and angiotensin antagonistic activities(Muller et al.,2002; Chambhare et al.2003). Recently, we have focused on the synthesis of fused heterocyclic systems containing thienopyrimidine via aza-wittig reaction at room temperature. Some X-ray crystal structures of fused pyrimidinone derivatives have been reported (Xie et al., 2007; Hu et al., 2007). The title compound (I) can be used as a new precursor for obtaining of bioactive molecules with fluorescence properties.

In (I) (Fig. 1), the piperidinyl ring has a distored chair conformation. The weak intermolecular C—H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2). The crystal packing exhibits relatively short intermolecular S···S distances of 3.590 (2) Å (Table 1), which is shorter than the sum of the van der Waals radii of the relevent atoms.

Experimental

To a solution of iminophosphorane(2mmol) in anhyd.CH₂Cl₂(10ml)aromatic isocyanate(2mmol)was added under nitrogen atmosphere at room temperature.After the reaction mixture was left unstirred for 6-12h at 0-5°C,the iminophosphorane had disappeared (TLC monitored).The solvent was removed off under redunced pressure and Et₂O/petroleum ether (1:2,20ml) was added to precipitate triphenylphosphine oxide. Removal of the solvent gave carbodiimides,which were used directly without further purification. To a solution of carbodiimides in CH₂Cl₂(10ml)dialkylamine(2mmol). After the reaction mixture was left unstirred for 4-6h. The solvent was removed and anhyd.EtOH(10ml)with several drops of EtONa in EtOH was added. The mixture was stirred for 6-12h at room temperature. The solution was condensed and residue was recrystallized from EtOH to give the expected title compound in a good yield.