1-(4,5,6,7-Tetra­hydro­thieno[3,2-c]pyridin-5-yl)-2-{4-[3-(trifluoro­meth­yl)phen­yl]piperazin-1-yl}ethanone

Shuang Zhi; Guo Zheng; Ying Liu; Deng-Ke Liu

doi:10.1107/S1600536812013591

. 2012 Apr 4;68(Pt 5):o1293. doi: 10.1107/S1600536812013591

1-(4,5,6,7-Tetrahydrothieno[3,2-c]pyridin-5-yl)-2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethanone

Shuang Zhi ^a, Guo Zheng ^b,^*, Ying Liu ^c, Deng-Ke Liu ^c

PMCID: PMC3344441 PMID: 22590203

Abstract

In the title molecule, C₂₀H₂₂F₃N₃OS, the piperazine ring has a chair conformation, and the N—C(=O)—C—N torsion angle is −59.42 (14)°. In the crystal, weak C—H⋯O and C—H⋯π interactions link the molecules into layers parallel to (101).

Related literature

For details of the synthesis, see: Liu et al. (2008 ▶). For related structures, see: Niu et al. (2011 ▶); Zhi et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₂₂F₃N₃OS
M _r = 409.47
Monoclinic,
a = 32.692 (6) Å
b = 6.3772 (11) Å
c = 18.215 (3) Å
β = 92.985 (2)°
V = 3792.5 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.958, T _max = 0.975
18550 measured reflections
4523 independent reflections
3449 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.097
S = 1.03
4523 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013591/cv5266sup1.cif

e-68-o1293-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013591/cv5266Isup2.hkl

e-68-o1293-Isup2.hkl^{(221.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013591/cv5266Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812013591/cv5266Isup4.cml

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

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

Cg is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1ⁱ	0.99	2.56	3.4709 (17)	153
C13—H13B⋯O1ⁱⁱ	0.99	2.60	3.3607 (16)	133
C16—H16⋯Cgⁱⁱⁱ	0.95	2.61	3.3641 (13)	136

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

Acknowledgments

The authors thank Mr Hai-Bin Song of Nankai University for the X-ray crystallographic determination and for helpful suggestions.

supplementary crystallographic information

Comment

As a continuation of structural studies of thienopyridine derivatives (Niu et al., 2011; Zhi et al., 2011), we present here the title compound (I), which exhibits the antiplatelet aggregation ratio higher than ticlopidine.

In (I) (Fig. 1), pyridine ring with a half chair conformation is linked into the piperazine ring exhibiting a chair conformation by N1—C8—C9—N2 with a torsion angle of -59.42 (14)°. The dihedral angles formed between the thiophene plane(A), the phenyl ring (B) and the C10—C11—C12—C13 plane (C) are 29.48 (6)° (AB), 41.19 (7)° (AC) and 13.77 (8)° (BC), respectively. In the crystal structure, weak intermolecular C—H···O and C—H···π interactions (Table 1) link the molecules into layers parallel to (101).

Experimental

Chloracetyl chloride was dropwised into the mixture of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine, TEA and dichloromethane at 268 K. After stirring for 3 h, the solvent was evaporated and a light yellow oily substance was obtained by silica gel column chromatography. The light yellow oily substance then reacted with 1-(3-(trifluoromethyl) phenyl)piperazine in a mixture of acetonitrile and TEA. After stirring for 7 h at room temperature, the compound (I) was obtained by silica gel column chromatography (Liu et al., 2008). Crystallization of the obtained yellow solid from acetone afforded light yellow crystals suitble for X-ray analysis.