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

Zhi, S.; Zheng, G.; Liu, Y.; Liu, D.-K.

doi:10.1107/S1600536812013591

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1293

doi:10.1107/S1600536812013591

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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 and Deng-Ke Liu ^c

^aSchool of Environmental and Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China, ^bTianjin Textile Fiber Interface Processing Technology Engineering Center, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China, and ^cTianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
^*Correspondence e-mail: zhengguo@tjpu.edu.cn

(Received 19 March 2012; accepted 29 March 2012; online 4 April 2012)

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, C 2/c
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[F² > 2σ(F²)] = 0.032
wR(F²) = 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

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
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x, y-1, z; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812013591/cv5266sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812013591/cv5266Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812013591/cv5266Isup4.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I)showing the atom-numbering scheme and 50% probability displacement ellipsoids.

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

Crystal data top

C₂₀H₂₂F₃N₃OS	F(000) = 1712
M_r = 409.47	D_x = 1.434 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6174 reflections
a = 32.692 (6) Å	θ = 1.2–27.9°
b = 6.3772 (11) Å	µ = 0.22 mm⁻¹
c = 18.215 (3) Å	T = 113 K
β = 92.985 (2)°	Prism, colourless
V = 3792.5 (11) Å³	0.20 × 0.18 × 0.12 mm
Z = 8

Data collection top

Rigaku Saturn724 CCD diffractometer	4523 independent reflections
Radiation source: rotating anode	3449 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.033
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 1.3°
ω and ϕ scans	h = −42→40
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −8→8
T_min = 0.958, T_max = 0.975	l = −23→23
18550 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0608P)²] where P = (F_o² + 2F_c²)/3
4523 reflections	(Δ/σ)_max = 0.005
253 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₀H₂₂F₃N₃OS	V = 3792.5 (11) Å³
M_r = 409.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 32.692 (6) Å	µ = 0.22 mm⁻¹
b = 6.3772 (11) Å	T = 113 K
c = 18.215 (3) Å	0.20 × 0.18 × 0.12 mm
β = 92.985 (2)°

Data collection top

Rigaku Saturn724 CCD diffractometer	4523 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3449 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.975	R_int = 0.033
18550 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
4523 reflections	Δρ_min = −0.33 e Å⁻³
253 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	1.129431 (9)	0.80354 (5)	0.452757 (18)	0.02545 (10)
F1	0.76604 (3)	0.73309 (12)	0.07407 (4)	0.0338 (2)
F2	0.72213 (2)	0.48600 (13)	0.05611 (5)	0.0396 (2)
F3	0.78186 (3)	0.46014 (14)	0.01330 (4)	0.0394 (2)
O1	0.97125 (3)	1.18330 (14)	0.40862 (6)	0.0298 (2)
N1	1.00374 (3)	0.91401 (16)	0.35494 (6)	0.0198 (2)
N2	0.92131 (3)	0.71911 (15)	0.37376 (6)	0.0174 (2)
N3	0.84845 (3)	0.54625 (15)	0.30117 (5)	0.0170 (2)
C1	1.14276 (4)	1.0434 (2)	0.41862 (8)	0.0293 (3)
H1	1.1687	1.1077	0.4280	0.035*
C2	1.11183 (4)	1.1299 (2)	0.37667 (7)	0.0266 (3)
H2	1.1137	1.2619	0.3529	0.032*
C3	1.07608 (3)	1.0008 (2)	0.37202 (7)	0.0206 (3)
C4	1.03599 (4)	1.0538 (2)	0.33102 (7)	0.0238 (3)
H4A	1.0286	1.2013	0.3408	0.029*
H4B	1.0389	1.0378	0.2775	0.029*
C5	1.01539 (4)	0.69138 (19)	0.35519 (7)	0.0215 (3)
H5A	1.0255	0.6524	0.3067	0.026*
H5B	0.9912	0.6036	0.3642	0.026*
C6	1.04896 (4)	0.6520 (2)	0.41531 (7)	0.0221 (3)
H6A	1.0372	0.6564	0.4643	0.026*
H6B	1.0612	0.5118	0.4087	0.026*
C7	1.08114 (3)	0.81855 (19)	0.41028 (7)	0.0198 (3)
C8	0.97449 (4)	0.99396 (19)	0.39714 (7)	0.0194 (3)
C9	0.94467 (4)	0.84037 (19)	0.42992 (7)	0.0201 (3)
H9A	0.9602	0.7426	0.4632	0.024*
H9B	0.9254	0.9193	0.4597	0.024*
C10	0.89218 (4)	0.85104 (19)	0.33157 (7)	0.0207 (3)
H10A	0.9069	0.9690	0.3095	0.025*
H10B	0.8721	0.9103	0.3648	0.025*
C11	0.86980 (4)	0.72588 (19)	0.27125 (7)	0.0212 (3)
H11A	0.8498	0.8176	0.2442	0.025*
H11B	0.8897	0.6758	0.2360	0.025*
C12	0.87583 (4)	0.4201 (2)	0.35010 (7)	0.0240 (3)
H12A	0.8962	0.3479	0.3206	0.029*
H12B	0.8596	0.3116	0.3744	0.029*
C13	0.89803 (4)	0.55328 (19)	0.40811 (7)	0.0232 (3)
H13A	0.8779	0.6166	0.4404	0.028*
H13B	0.9169	0.4642	0.4389	0.028*
C14	0.82152 (3)	0.43532 (18)	0.25274 (6)	0.0163 (2)
C15	0.80737 (3)	0.23339 (18)	0.26919 (7)	0.0183 (3)
H15	0.8172	0.1666	0.3133	0.022*
C16	0.77936 (3)	0.12972 (19)	0.22235 (7)	0.0192 (3)
H16	0.7707	−0.0075	0.2347	0.023*
C17	0.76363 (4)	0.22165 (18)	0.15800 (7)	0.0193 (3)
H17	0.7441	0.1510	0.1264	0.023*
C18	0.77749 (3)	0.42091 (18)	0.14144 (6)	0.0179 (2)
C19	0.80626 (3)	0.52536 (18)	0.18650 (6)	0.0173 (2)
H19	0.8158	0.6595	0.1724	0.021*
C20	0.76198 (4)	0.5249 (2)	0.07173 (7)	0.0233 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01591 (16)	0.0367 (2)	0.02358 (18)	0.00031 (13)	−0.00047 (12)	−0.00149 (14)
F1	0.0528 (5)	0.0192 (4)	0.0272 (4)	−0.0012 (3)	−0.0169 (4)	0.0034 (3)
F2	0.0294 (4)	0.0463 (5)	0.0411 (5)	−0.0079 (4)	−0.0182 (4)	0.0124 (4)
F3	0.0558 (5)	0.0456 (5)	0.0166 (4)	0.0109 (4)	0.0013 (4)	−0.0002 (4)
O1	0.0313 (5)	0.0203 (5)	0.0382 (6)	0.0007 (4)	0.0039 (4)	−0.0036 (4)
N1	0.0175 (5)	0.0211 (5)	0.0205 (5)	−0.0011 (4)	−0.0016 (4)	0.0002 (4)
N2	0.0159 (5)	0.0179 (5)	0.0180 (5)	−0.0004 (4)	−0.0035 (4)	0.0012 (4)
N3	0.0172 (5)	0.0158 (5)	0.0175 (5)	−0.0016 (4)	−0.0039 (4)	0.0039 (4)
C1	0.0185 (6)	0.0419 (8)	0.0278 (7)	−0.0089 (6)	0.0047 (5)	−0.0034 (6)
C2	0.0240 (6)	0.0319 (7)	0.0245 (7)	−0.0068 (6)	0.0067 (5)	−0.0006 (6)
C3	0.0184 (6)	0.0268 (6)	0.0166 (6)	−0.0019 (5)	0.0026 (5)	−0.0033 (5)
C4	0.0221 (6)	0.0272 (7)	0.0220 (6)	−0.0042 (5)	−0.0006 (5)	0.0030 (5)
C5	0.0198 (6)	0.0220 (6)	0.0224 (7)	0.0009 (5)	−0.0014 (5)	−0.0057 (5)
C6	0.0202 (6)	0.0205 (6)	0.0253 (7)	0.0019 (5)	−0.0014 (5)	−0.0020 (5)
C7	0.0160 (6)	0.0256 (6)	0.0176 (6)	0.0004 (5)	−0.0005 (5)	−0.0049 (5)
C8	0.0178 (6)	0.0220 (6)	0.0179 (6)	0.0004 (5)	−0.0056 (5)	−0.0009 (5)
C9	0.0190 (6)	0.0227 (6)	0.0184 (6)	−0.0001 (5)	−0.0016 (5)	−0.0022 (5)
C10	0.0221 (6)	0.0159 (6)	0.0236 (7)	−0.0005 (5)	−0.0046 (5)	0.0021 (5)
C11	0.0236 (6)	0.0178 (6)	0.0215 (6)	−0.0050 (5)	−0.0062 (5)	0.0054 (5)
C12	0.0275 (6)	0.0179 (6)	0.0256 (7)	−0.0021 (5)	−0.0096 (5)	0.0072 (5)
C13	0.0238 (6)	0.0232 (6)	0.0216 (6)	−0.0037 (5)	−0.0073 (5)	0.0066 (5)
C14	0.0135 (5)	0.0172 (6)	0.0181 (6)	0.0019 (4)	0.0015 (4)	0.0003 (5)
C15	0.0171 (5)	0.0179 (6)	0.0198 (6)	0.0012 (5)	0.0010 (5)	0.0028 (5)
C16	0.0187 (6)	0.0153 (6)	0.0240 (6)	−0.0010 (4)	0.0042 (5)	0.0007 (5)
C17	0.0185 (6)	0.0191 (6)	0.0201 (6)	−0.0006 (5)	−0.0003 (5)	−0.0043 (5)
C18	0.0190 (6)	0.0192 (6)	0.0156 (6)	0.0022 (4)	−0.0002 (5)	−0.0006 (5)
C19	0.0183 (5)	0.0152 (6)	0.0182 (6)	−0.0003 (4)	0.0003 (5)	0.0017 (5)
C20	0.0284 (7)	0.0209 (7)	0.0197 (6)	−0.0021 (5)	−0.0053 (5)	−0.0021 (5)

Geometric parameters (Å, º) top

S1—C1	1.7161 (14)	C6—H6A	0.9900
S1—C7	1.7241 (12)	C6—H6B	0.9900
F1—C20	1.3350 (14)	C8—C9	1.5254 (17)
F2—C20	1.3420 (14)	C9—H9A	0.9900
F3—C20	1.3407 (15)	C9—H9B	0.9900
O1—C8	1.2309 (15)	C10—C11	1.5153 (16)
N1—C8	1.3571 (15)	C10—H10A	0.9900
N1—C4	1.4644 (16)	C10—H10B	0.9900
N1—C5	1.4699 (16)	C11—H11A	0.9900
N2—C10	1.4591 (15)	C11—H11B	0.9900
N2—C13	1.4624 (15)	C12—C13	1.5114 (17)
N2—C9	1.4651 (15)	C12—H12A	0.9900
N3—C14	1.4047 (15)	C12—H12B	0.9900
N3—C11	1.4617 (15)	C13—H13A	0.9900
N3—C12	1.4695 (15)	C13—H13B	0.9900
C1—C2	1.3528 (19)	C14—C19	1.4041 (16)
C1—H1	0.9500	C14—C15	1.4059 (16)
C2—C3	1.4288 (17)	C15—C16	1.3865 (17)
C2—H2	0.9500	C15—H15	0.9500
C3—C7	1.3606 (18)	C16—C17	1.3854 (17)
C3—C4	1.5124 (17)	C16—H16	0.9500
C4—H4A	0.9900	C17—C18	1.3877 (17)
C4—H4B	0.9900	C17—H17	0.9500
C5—C6	1.5301 (17)	C18—C19	1.3860 (16)
C5—H5A	0.9900	C18—C20	1.4973 (17)
C5—H5B	0.9900	C19—H19	0.9500
C6—C7	1.5013 (17)

C1—S1—C7	91.82 (6)	N2—C10—C11	110.82 (10)
C8—N1—C4	118.63 (11)	N2—C10—H10A	109.5
C8—N1—C5	123.45 (10)	C11—C10—H10A	109.5
C4—N1—C5	113.49 (10)	N2—C10—H10B	109.5
C10—N2—C13	107.61 (9)	C11—C10—H10B	109.5
C10—N2—C9	111.45 (9)	H10A—C10—H10B	108.1
C13—N2—C9	110.30 (10)	N3—C11—C10	111.36 (10)
C14—N3—C11	117.15 (10)	N3—C11—H11A	109.4
C14—N3—C12	116.58 (10)	C10—C11—H11A	109.4
C11—N3—C12	111.56 (9)	N3—C11—H11B	109.4
C2—C1—S1	111.82 (10)	C10—C11—H11B	109.4
C2—C1—H1	124.1	H11A—C11—H11B	108.0
S1—C1—H1	124.1	N3—C12—C13	111.82 (10)
C1—C2—C3	112.56 (12)	N3—C12—H12A	109.3
C1—C2—H2	123.7	C13—C12—H12A	109.3
C3—C2—H2	123.7	N3—C12—H12B	109.3
C7—C3—C2	112.61 (11)	C13—C12—H12B	109.3
C7—C3—C4	121.55 (11)	H12A—C12—H12B	107.9
C2—C3—C4	125.83 (12)	N2—C13—C12	110.42 (10)
N1—C4—C3	109.61 (10)	N2—C13—H13A	109.6
N1—C4—H4A	109.7	C12—C13—H13A	109.6
C3—C4—H4A	109.7	N2—C13—H13B	109.6
N1—C4—H4B	109.7	C12—C13—H13B	109.6
C3—C4—H4B	109.7	H13A—C13—H13B	108.1
H4A—C4—H4B	108.2	C19—C14—N3	121.12 (10)
N1—C5—C6	109.69 (10)	C19—C14—C15	116.85 (10)
N1—C5—H5A	109.7	N3—C14—C15	121.99 (10)
C6—C5—H5A	109.7	C16—C15—C14	121.31 (11)
N1—C5—H5B	109.7	C16—C15—H15	119.3
C6—C5—H5B	109.7	C14—C15—H15	119.3
H5A—C5—H5B	108.2	C17—C16—C15	121.54 (11)
C7—C6—C5	108.60 (11)	C17—C16—H16	119.2
C7—C6—H6A	110.0	C15—C16—H16	119.2
C5—C6—H6A	110.0	C16—C17—C18	117.41 (11)
C7—C6—H6B	110.0	C16—C17—H17	121.3
C5—C6—H6B	110.0	C18—C17—H17	121.3
H6A—C6—H6B	108.4	C19—C18—C17	122.05 (11)
C3—C7—C6	124.64 (11)	C19—C18—C20	118.61 (10)
C3—C7—S1	111.19 (9)	C17—C18—C20	119.32 (11)
C6—C7—S1	124.17 (10)	C18—C19—C14	120.80 (11)
O1—C8—N1	122.29 (12)	C18—C19—H19	119.6
O1—C8—C9	120.06 (11)	C14—C19—H19	119.6
N1—C8—C9	117.65 (11)	F1—C20—F3	106.27 (11)
N2—C9—C8	112.71 (10)	F1—C20—F2	106.51 (10)
N2—C9—H9A	109.0	F3—C20—F2	106.27 (10)
C8—C9—H9A	109.0	F1—C20—C18	112.62 (10)
N2—C9—H9B	109.0	F3—C20—C18	112.34 (10)
C8—C9—H9B	109.0	F2—C20—C18	112.35 (11)
H9A—C9—H9B	107.8

C7—S1—C1—C2	−0.21 (11)	C14—N3—C11—C10	170.67 (10)
S1—C1—C2—C3	0.45 (15)	C12—N3—C11—C10	−51.32 (14)
C1—C2—C3—C7	−0.53 (17)	N2—C10—C11—N3	57.59 (13)
C1—C2—C3—C4	178.54 (12)	C14—N3—C12—C13	−170.23 (10)
C8—N1—C4—C3	108.44 (12)	C11—N3—C12—C13	51.50 (14)
C5—N1—C4—C3	−48.79 (14)	C10—N2—C13—C12	61.50 (13)
C7—C3—C4—N1	14.37 (17)	C9—N2—C13—C12	−176.74 (10)
C2—C3—C4—N1	−164.62 (12)	N3—C12—C13—N2	−57.23 (14)
C8—N1—C5—C6	−87.88 (13)	C11—N3—C14—C19	−18.70 (16)
C4—N1—C5—C6	68.10 (13)	C12—N3—C14—C19	−154.62 (11)
N1—C5—C6—C7	−46.98 (13)	C11—N3—C14—C15	163.73 (11)
C2—C3—C7—C6	−179.84 (11)	C12—N3—C14—C15	27.81 (16)
C4—C3—C7—C6	1.05 (19)	C19—C14—C15—C16	−0.63 (17)
C2—C3—C7—S1	0.36 (14)	N3—C14—C15—C16	177.05 (11)
C4—C3—C7—S1	−178.75 (10)	C14—C15—C16—C17	−1.02 (18)
C5—C6—C7—C3	15.39 (17)	C15—C16—C17—C18	1.02 (17)
C5—C6—C7—S1	−164.84 (9)	C16—C17—C18—C19	0.64 (17)
C1—S1—C7—C3	−0.09 (10)	C16—C17—C18—C20	178.81 (11)
C1—S1—C7—C6	−179.89 (11)	C17—C18—C19—C14	−2.33 (18)
C4—N1—C8—O1	8.89 (18)	C20—C18—C19—C14	179.49 (10)
C5—N1—C8—O1	163.72 (11)	N3—C14—C19—C18	−175.44 (10)
C4—N1—C8—C9	−171.93 (10)	C15—C14—C19—C18	2.25 (17)
C5—N1—C8—C9	−17.10 (16)	C19—C18—C20—F1	−23.30 (16)
C10—N2—C9—C8	−69.20 (13)	C17—C18—C20—F1	158.47 (11)
C13—N2—C9—C8	171.33 (9)	C19—C18—C20—F3	96.66 (13)
O1—C8—C9—N2	119.78 (12)	C17—C18—C20—F3	−81.57 (14)
N1—C8—C9—N2	−59.42 (14)	C19—C18—C20—F2	−143.58 (11)
C13—N2—C10—C11	−61.83 (13)	C17—C18—C20—F2	38.19 (16)
C9—N2—C10—C11	177.12 (10)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x, y−1, z; (iii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂F₃N₃OS
M_r	409.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	32.692 (6), 6.3772 (11), 18.215 (3)
β (°)	92.985 (2)
V (Å³)	3792.5 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.958, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	18550, 4523, 3449
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.097, 1.03
No. of reflections	4523
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.33

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

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)	153.1
C13—H13B···O1ⁱⁱ	0.99	2.60	3.3607 (16)	133.4
C16—H16···Cgⁱⁱⁱ	0.95	2.61	3.3641 (13)	136

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x, y−1, z; (iii) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

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

References

Liu, D. K., Liu, Y., Liu, M., Zhang, S. J., Cheng, D., Jin, L. Y., Xu, W. R. & Liu, C. X. (2008). CN Patent 101284838A. Google Scholar
Niu, D., Huang, S.-Y., Wang, P.-B. & Liu, D.-K. (2011). Acta Cryst. E67, o2134. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhi, S., Zheng, G., Liu, Y., Wang, J. Y. & Liu, D. K. (2011). Chin. J. Synth. Chem. 6, 730-733. Google Scholar

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Volume 68| Part 5| May 2012| Page o1293

doi:10.1107/S1600536812013591

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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