1-(4,5,6,7-Tetra-hydro-thieno[3,2-c]pyridin-5-yl)-2-{4-[3-(trifluoro-meth-yl)phen-yl]piperazin-1-yl}ethanone.

In the title mol-ecule, C(20)H(22)F(3)N(3)OS, 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 inter-actions link the mol-ecules 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 = 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

Δρmax = 0.33 e Å−3

Δρmin = −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 ▶).

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

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

C20H22F3N3OS	F(000) = 1712
Mr = 409.47	Dx = 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

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

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(Fo2) + (0.0608P)2] where P = (Fo2 + 2Fc2)/3
4523 reflections	(Δ/σ)max = 0.005
253 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .