2-[4-(4-Methylphenylsulfonyl)piperazin-1-yl]-1-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone

Niu, D.; Huang, S.-Y.; Wang, P.-B.; Liu, D.-K.

doi:10.1107/S1600536811028716

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2134

doi:10.1107/S1600536811028716

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2-[4-(4-Methylphenylsulfonyl)piperazin-1-yl]-1-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone

Duan Niu,^a Shu-Yun Huang,^b Ping-Bao Wang ^b and Deng-Ke Liu ^b ^*

^aTianjin Medical University, Tianjin 300070, People's Republic of China, and ^bTianjin Institute of Pharmaceutical Research, Tianjin, 300193, People's Republic of China
^*Correspondence e-mail: liudk@tjipr.com

(Received 27 June 2011; accepted 17 July 2011; online 23 July 2011)

In the title thienopyridine derivative, C₂₀H₂₅N₃O₃S₂, the piperazine ring exhibits a chair conformation and the tetrahydropyridine ring exhibits a half-chair conformation. The folded conformation of the molecule is defined by the N—C—C—N torsion angle of −70.20 (2) °. Intermolecular C—H⋯S and C—H⋯O hydrogen bonds help to establish the packing.

Related literature

For background to the bioactivity and applications of the title compound, see: Cattaneo (2009 ); Wallentin (2009 ). For a related structure, see: Zhi et al. (2011 ). For the synthesis of the title compound, see: Liu et al. (2008 ).

Experimental

Crystal data

C₂₀H₂₅N₃O₃S₂
M_r = 419.55
Orthorhombic, P b c a
a = 13.062 (2) Å
b = 15.710 (3) Å
c = 19.798 (3) Å
V = 4062.8 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.934, T_max = 0.950
49454 measured reflections
4844 independent reflections
4463 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.143
S = 1.14
4844 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 1.17 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯S1ⁱ	0.99	2.77	3.469 (2)	128
C6—H6A⋯O1ⁱⁱ	0.99	2.52	3.470 (3)	161
C6—H6B⋯O2ⁱⁱⁱ	0.99	2.51	3.346 (3)	143
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) -x, -y+2, -z+1; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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/S1600536811028716/fl2350sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028716/fl2350Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028716/fl2350Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811028716/fl2350Isup4.cml

checkCIF report

Comment top

As a thienopyridine derivative, the title compound(I) can be used as an irreversible P2Y12 antagonist to inhibit ADP, which induces platelet aggregation and decreases the risk of arterial occlusion. (Cattaneo 2009; Wallentin 2009).

The piperazine ring exhibits a chair conformation and the tetrahydropyridine ring exhibits a half chair conformation (Fig. 1). The folded conformation of the molecule is defined by the N1—C8—C9—N2 torsion angle of -70.20 (2) °. The dihedral angles formed between the tetrahydropyridine plane and the phenyl ring and the C10—C11—C12—C13 plane are 85.47 (6) ° and 56.38 (9) °, respectively. The crystal is stabilized by intermolecular C—H···S and C—H···O hydrogen bonds (Table1, Fig.2).

Related literature top

For background to the bioactivity and applications of the title compound, see: Cattaneo (2009); Wallentin (2009). For a related structure, see: Zhi et al. (2011). For the synthesis of the title compound, see: Liu et al. (2008).

Experimental top

2-Chloroacetyl chloride was added dropwise into a mixture of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine, dichloromethane and TEA at 263k-273k. 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 was then dissloved in a mixture of acetonitrile, TEA and 1-tosylpiperazine. After stirring for 5 h, the title compound was obtained by silica gel column chromatography. Crystallization of the resultingg white solid from methanol afforded white 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), with the atom-numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram for (I) with hydrogen bonds drawn as dashed lines.

2-[4-(4-Methylphenylsulfonyl)piperazin-1-yl]-1-(4,5,6,7- tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone top

Crystal data top

C₂₀H₂₅N₃O₃S₂	F(000) = 1776
M_r = 419.55	D_x = 1.372 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 12748 reflections
a = 13.062 (2) Å	θ = 1.7–28.0°
b = 15.710 (3) Å	µ = 0.29 mm⁻¹
c = 19.798 (3) Å	T = 113 K
V = 4062.8 (11) Å³	Prism, colorless
Z = 8	0.24 × 0.20 × 0.18 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4844 independent reflections
Radiation source: rotating anode	4463 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.054
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω and ϕ scans	h = −17→17
Absorption correction: multi-scan CrystalClear	k = −20→20
T_min = 0.934, T_max = 0.950	l = −26→25
49454 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0665P)² + 2.3859P] where P = (F_o² + 2F_c²)/3
4844 reflections	(Δ/σ)_max = 0.002
254 parameters	Δρ_max = 1.17 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₀H₂₅N₃O₃S₂	V = 4062.8 (11) Å³
M_r = 419.55	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.062 (2) Å	µ = 0.29 mm⁻¹
b = 15.710 (3) Å	T = 113 K
c = 19.798 (3) Å	0.24 × 0.20 × 0.18 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4844 independent reflections
Absorption correction: multi-scan CrystalClear	4463 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.950	R_int = 0.054
49454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.14	Δρ_max = 1.17 e Å⁻³
4844 reflections	Δρ_min = −0.34 e Å⁻³
254 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	−0.12585 (4)	0.69571 (4)	0.50761 (3)	0.03055 (16)
S2	0.51658 (4)	1.09372 (3)	0.30610 (3)	0.03065 (16)
O1	0.13122 (12)	1.01184 (10)	0.57588 (8)	0.0348 (4)
O2	0.58272 (13)	1.14367 (10)	0.34791 (9)	0.0400 (4)
O3	0.48630 (14)	1.12484 (11)	0.24122 (9)	0.0420 (4)
N1	0.12333 (13)	0.89002 (11)	0.51535 (9)	0.0273 (4)
N2	0.23688 (12)	1.01546 (10)	0.41984 (8)	0.0244 (4)
N3	0.41057 (13)	1.07905 (11)	0.34905 (9)	0.0271 (4)
C1	−0.11495 (17)	0.69019 (14)	0.59285 (13)	0.0329 (5)
H1	−0.1601	0.6579	0.6204	0.039*
C2	−0.03617 (16)	0.73600 (13)	0.61798 (11)	0.0293 (4)
H2	−0.0186	0.7390	0.6645	0.035*
C3	0.01696 (15)	0.77916 (12)	0.56530 (10)	0.0240 (4)
C4	0.10712 (17)	0.83828 (14)	0.57598 (11)	0.0306 (5)
H4A	0.0937	0.8758	0.6152	0.037*
H4B	0.1694	0.8045	0.5857	0.037*
C5	0.11965 (16)	0.84157 (14)	0.45193 (11)	0.0278 (4)
H5A	0.1705	0.7949	0.4538	0.033*
H5B	0.1384	0.8795	0.4139	0.033*
C6	0.01385 (16)	0.80409 (14)	0.43904 (10)	0.0277 (4)
H6A	−0.0342	0.8495	0.4249	0.033*
H6B	0.0174	0.7610	0.4026	0.033*
C7	−0.02224 (15)	0.76393 (13)	0.50316 (11)	0.0252 (4)
C8	0.13226 (14)	0.97516 (13)	0.52092 (11)	0.0266 (4)
C9	0.13997 (15)	1.02709 (14)	0.45566 (12)	0.0302 (5)
H9A	0.0831	1.0106	0.4253	0.036*
H9B	0.1316	1.0882	0.4667	0.036*
C10	0.32177 (15)	1.05628 (13)	0.45626 (11)	0.0260 (4)
H10A	0.3281	1.0309	0.5018	0.031*
H10B	0.3072	1.1177	0.4617	0.031*
C11	0.42175 (15)	1.04500 (14)	0.41822 (10)	0.0264 (4)
H11A	0.4774	1.0755	0.4420	0.032*
H11B	0.4399	0.9839	0.4163	0.032*
C12	0.32501 (17)	1.03841 (14)	0.31276 (11)	0.0306 (5)
H12A	0.3378	0.9766	0.3081	0.037*
H12B	0.3183	1.0632	0.2670	0.037*
C13	0.22808 (17)	1.05332 (15)	0.35261 (11)	0.0321 (5)
H13A	0.2155	1.1152	0.3568	0.039*
H13B	0.1693	1.0278	0.3285	0.039*
C14	0.57571 (17)	0.99377 (13)	0.29458 (10)	0.0273 (4)
C15	0.66141 (17)	0.97308 (14)	0.33228 (11)	0.0305 (5)
H15	0.6860	1.0112	0.3658	0.037*
C16	0.71122 (18)	0.89631 (15)	0.32094 (12)	0.0344 (5)
H16	0.7705	0.8825	0.3465	0.041*
C17	0.67544 (18)	0.83934 (14)	0.27257 (11)	0.0335 (5)
C18	0.58779 (19)	0.86056 (14)	0.23633 (11)	0.0334 (5)
H18	0.5617	0.8215	0.2040	0.040*
C19	0.53773 (18)	0.93727 (14)	0.24632 (11)	0.0304 (5)
H19	0.4785	0.9512	0.2207	0.037*
C20	0.7307 (2)	0.75663 (16)	0.25933 (14)	0.0474 (6)
H20A	0.7981	0.7581	0.2810	0.071*
H20B	0.7392	0.7488	0.2105	0.071*
H20C	0.6907	0.7093	0.2778	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0261 (3)	0.0310 (3)	0.0345 (3)	−0.0073 (2)	0.0029 (2)	−0.0032 (2)
S2	0.0320 (3)	0.0252 (3)	0.0348 (3)	−0.0070 (2)	0.0075 (2)	−0.0003 (2)
O1	0.0353 (9)	0.0313 (8)	0.0377 (9)	−0.0053 (7)	−0.0024 (7)	−0.0032 (7)
O2	0.0348 (9)	0.0328 (8)	0.0523 (10)	−0.0150 (7)	0.0129 (7)	−0.0125 (7)
O3	0.0482 (10)	0.0385 (9)	0.0391 (9)	−0.0008 (8)	0.0106 (8)	0.0138 (8)
N1	0.0287 (9)	0.0259 (9)	0.0274 (9)	−0.0068 (7)	0.0013 (7)	0.0031 (7)
N2	0.0197 (8)	0.0239 (8)	0.0295 (9)	−0.0049 (6)	−0.0029 (6)	0.0043 (7)
N3	0.0251 (9)	0.0267 (9)	0.0296 (9)	−0.0061 (7)	0.0007 (7)	0.0000 (7)
C1	0.0266 (11)	0.0255 (10)	0.0466 (13)	0.0001 (8)	0.0003 (9)	−0.0044 (9)
C2	0.0326 (11)	0.0271 (10)	0.0281 (11)	0.0028 (9)	0.0004 (8)	0.0047 (8)
C3	0.0261 (10)	0.0202 (9)	0.0258 (10)	0.0021 (7)	0.0017 (8)	0.0020 (7)
C4	0.0348 (11)	0.0304 (11)	0.0266 (11)	−0.0048 (9)	−0.0019 (8)	0.0035 (9)
C5	0.0266 (10)	0.0281 (10)	0.0287 (11)	−0.0057 (8)	0.0007 (8)	0.0012 (8)
C6	0.0290 (10)	0.0304 (11)	0.0238 (10)	−0.0041 (8)	0.0012 (8)	−0.0015 (8)
C7	0.0246 (10)	0.0219 (9)	0.0290 (10)	0.0001 (8)	0.0009 (8)	−0.0023 (8)
C8	0.0159 (9)	0.0266 (10)	0.0372 (12)	−0.0027 (7)	−0.0010 (8)	0.0012 (9)
C9	0.0197 (9)	0.0280 (10)	0.0428 (13)	−0.0018 (8)	−0.0005 (8)	0.0067 (9)
C10	0.0225 (9)	0.0252 (9)	0.0302 (10)	−0.0060 (8)	−0.0009 (8)	−0.0014 (8)
C11	0.0219 (9)	0.0288 (10)	0.0286 (10)	−0.0053 (8)	−0.0025 (8)	−0.0017 (8)
C12	0.0328 (11)	0.0309 (11)	0.0282 (11)	−0.0097 (9)	−0.0051 (8)	0.0040 (8)
C13	0.0269 (10)	0.0340 (11)	0.0356 (12)	−0.0071 (9)	−0.0075 (9)	0.0110 (9)
C14	0.0315 (11)	0.0273 (10)	0.0231 (10)	−0.0076 (8)	0.0059 (8)	−0.0021 (8)
C15	0.0307 (11)	0.0356 (11)	0.0251 (10)	−0.0085 (9)	0.0022 (8)	−0.0038 (9)
C16	0.0311 (11)	0.0380 (12)	0.0342 (12)	−0.0022 (9)	0.0022 (9)	0.0020 (9)
C17	0.0385 (12)	0.0306 (11)	0.0316 (11)	−0.0045 (9)	0.0118 (9)	0.0007 (9)
C18	0.0467 (13)	0.0304 (11)	0.0230 (10)	−0.0113 (10)	0.0065 (9)	−0.0045 (8)
C19	0.0355 (11)	0.0332 (11)	0.0225 (10)	−0.0075 (9)	−0.0003 (8)	0.0002 (8)
C20	0.0517 (16)	0.0343 (12)	0.0561 (16)	0.0025 (11)	0.0162 (13)	−0.0035 (12)

Geometric parameters (Å, º) top

S1—C1	1.696 (3)	C6—H6B	0.9900
S1—C7	1.729 (2)	C8—C9	1.531 (3)
S2—O3	1.4302 (18)	C9—H9A	0.9900
S2—O2	1.4309 (17)	C9—H9B	0.9900
S2—N3	1.6412 (18)	C10—C11	1.518 (3)
S2—C14	1.765 (2)	C10—H10A	0.9900
O1—C8	1.231 (3)	C10—H10B	0.9900
N1—C8	1.347 (3)	C11—H11A	0.9900
N1—C4	1.465 (3)	C11—H11B	0.9900
N1—C5	1.469 (3)	C12—C13	1.510 (3)
N2—C9	1.462 (3)	C12—H12A	0.9900
N2—C13	1.463 (3)	C12—H12B	0.9900
N2—C10	1.470 (2)	C13—H13A	0.9900
N3—C12	1.474 (3)	C13—H13B	0.9900
N3—C11	1.478 (3)	C14—C15	1.384 (3)
C1—C2	1.351 (3)	C14—C19	1.395 (3)
C1—H1	0.9500	C15—C16	1.389 (3)
C2—C3	1.424 (3)	C15—H15	0.9500
C2—H2	0.9500	C16—C17	1.392 (3)
C3—C7	1.354 (3)	C16—H16	0.9500
C3—C4	1.515 (3)	C17—C18	1.392 (3)
C4—H4A	0.9900	C17—C20	1.510 (3)
C4—H4B	0.9900	C18—C19	1.385 (3)
C5—C6	1.524 (3)	C18—H18	0.9500
C5—H5A	0.9900	C19—H19	0.9500
C5—H5B	0.9900	C20—H20A	0.9800
C6—C7	1.494 (3)	C20—H20B	0.9800
C6—H6A	0.9900	C20—H20C	0.9800

C1—S1—C7	90.96 (11)	N2—C9—H9B	108.9
O3—S2—O2	119.94 (11)	C8—C9—H9B	108.9
O3—S2—N3	106.26 (10)	H9A—C9—H9B	107.7
O2—S2—N3	106.67 (9)	N2—C10—C11	110.78 (16)
O3—S2—C14	108.00 (10)	N2—C10—H10A	109.5
O2—S2—C14	107.37 (11)	C11—C10—H10A	109.5
N3—S2—C14	108.14 (9)	N2—C10—H10B	109.5
C8—N1—C4	119.75 (18)	C11—C10—H10B	109.5
C8—N1—C5	125.96 (18)	H10A—C10—H10B	108.1
C4—N1—C5	114.08 (17)	N3—C11—C10	109.42 (17)
C9—N2—C13	108.82 (16)	N3—C11—H11A	109.8
C9—N2—C10	111.13 (16)	C10—C11—H11A	109.8
C13—N2—C10	109.16 (15)	N3—C11—H11B	109.8
C12—N3—C11	111.71 (16)	C10—C11—H11B	109.8
C12—N3—S2	116.61 (14)	H11A—C11—H11B	108.2
C11—N3—S2	116.59 (14)	N3—C12—C13	108.29 (18)
C2—C1—S1	113.78 (18)	N3—C12—H12A	110.0
C2—C1—H1	123.1	C13—C12—H12A	110.0
S1—C1—H1	123.1	N3—C12—H12B	110.0
C1—C2—C3	110.8 (2)	C13—C12—H12B	110.0
C1—C2—H2	124.6	H12A—C12—H12B	108.4
C3—C2—H2	124.6	N2—C13—C12	110.27 (17)
C7—C3—C2	113.39 (19)	N2—C13—H13A	109.6
C7—C3—C4	121.96 (18)	C12—C13—H13A	109.6
C2—C3—C4	124.64 (18)	N2—C13—H13B	109.6
N1—C4—C3	109.76 (17)	C12—C13—H13B	109.6
N1—C4—H4A	109.7	H13A—C13—H13B	108.1
C3—C4—H4A	109.7	C15—C14—C19	120.5 (2)
N1—C4—H4B	109.7	C15—C14—S2	119.55 (16)
C3—C4—H4B	109.7	C19—C14—S2	119.93 (18)
H4A—C4—H4B	108.2	C14—C15—C16	119.7 (2)
N1—C5—C6	111.90 (17)	C14—C15—H15	120.1
N1—C5—H5A	109.2	C16—C15—H15	120.1
C6—C5—H5A	109.2	C15—C16—C17	120.8 (2)
N1—C5—H5B	109.2	C15—C16—H16	119.6
C6—C5—H5B	109.2	C17—C16—H16	119.6
H5A—C5—H5B	107.9	C16—C17—C18	118.5 (2)
C7—C6—C5	107.88 (17)	C16—C17—C20	120.8 (2)
C7—C6—H6A	110.1	C18—C17—C20	120.7 (2)
C5—C6—H6A	110.1	C19—C18—C17	121.5 (2)
C7—C6—H6B	110.1	C19—C18—H18	119.2
C5—C6—H6B	110.1	C17—C18—H18	119.2
H6A—C6—H6B	108.4	C18—C19—C14	118.9 (2)
C3—C7—C6	125.32 (19)	C18—C19—H19	120.5
C3—C7—S1	111.06 (16)	C14—C19—H19	120.5
C6—C7—S1	123.52 (15)	C17—C20—H20A	109.5
O1—C8—N1	122.4 (2)	C17—C20—H20B	109.5
O1—C8—C9	119.81 (19)	H20A—C20—H20B	109.5
N1—C8—C9	117.75 (19)	C17—C20—H20C	109.5
N2—C9—C8	113.56 (17)	H20A—C20—H20C	109.5
N2—C9—H9A	108.9	H20B—C20—H20C	109.5
C8—C9—H9A	108.9

O3—S2—N3—C12	43.28 (18)	C10—N2—C9—C8	−71.2 (2)
O2—S2—N3—C12	172.33 (16)	O1—C8—C9—N2	112.0 (2)
C14—S2—N3—C12	−72.46 (17)	N1—C8—C9—N2	−70.2 (2)
O3—S2—N3—C11	178.81 (15)	C9—N2—C10—C11	−179.18 (16)
O2—S2—N3—C11	−52.14 (17)	C13—N2—C10—C11	−59.1 (2)
C14—S2—N3—C11	63.07 (16)	C12—N3—C11—C10	−56.6 (2)
C7—S1—C1—C2	−1.04 (18)	S2—N3—C11—C10	165.84 (13)
S1—C1—C2—C3	1.2 (2)	N2—C10—C11—N3	56.3 (2)
C1—C2—C3—C7	−0.7 (3)	C11—N3—C12—C13	58.5 (2)
C1—C2—C3—C4	178.0 (2)	S2—N3—C12—C13	−163.93 (14)
C8—N1—C4—C3	129.51 (19)	C9—N2—C13—C12	−177.01 (17)
C5—N1—C4—C3	−45.7 (2)	C10—N2—C13—C12	61.5 (2)
C7—C3—C4—N1	15.1 (3)	N3—C12—C13—N2	−60.7 (2)
C2—C3—C4—N1	−163.44 (19)	O3—S2—C14—C15	140.22 (17)
C8—N1—C5—C6	−110.0 (2)	O2—S2—C14—C15	9.6 (2)
C4—N1—C5—C6	64.8 (2)	N3—S2—C14—C15	−105.18 (18)
N1—C5—C6—C7	−46.2 (2)	O3—S2—C14—C19	−37.9 (2)
C2—C3—C7—C6	176.41 (19)	O2—S2—C14—C19	−168.58 (16)
C4—C3—C7—C6	−2.3 (3)	N3—S2—C14—C19	76.67 (18)
C2—C3—C7—S1	−0.1 (2)	C19—C14—C15—C16	1.4 (3)
C4—C3—C7—S1	−178.81 (16)	S2—C14—C15—C16	−176.74 (16)
C5—C6—C7—C3	17.4 (3)	C14—C15—C16—C17	−0.7 (3)
C5—C6—C7—S1	−166.53 (15)	C15—C16—C17—C18	−0.8 (3)
C1—S1—C7—C3	0.62 (17)	C15—C16—C17—C20	178.8 (2)
C1—S1—C7—C6	−175.95 (18)	C16—C17—C18—C19	1.6 (3)
C4—N1—C8—O1	2.8 (3)	C20—C17—C18—C19	−178.0 (2)
C5—N1—C8—O1	177.38 (19)	C17—C18—C19—C14	−0.9 (3)
C4—N1—C8—C9	−174.92 (17)	C15—C14—C19—C18	−0.6 (3)
C5—N1—C8—C9	−0.4 (3)	S2—C14—C19—C18	177.51 (16)
C13—N2—C9—C8	168.59 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···S1ⁱ	0.99	2.77	3.469 (2)	128
C6—H6A···O1ⁱⁱ	0.99	2.52	3.470 (3)	161
C6—H6B···O2ⁱⁱⁱ	0.99	2.51	3.346 (3)	143

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₅N₃O₃S₂
M_r	419.55
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	113
a, b, c (Å)	13.062 (2), 15.710 (3), 19.798 (3)
V (Å³)	4062.8 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan CrystalClear
T_min, T_max	0.934, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	49454, 4844, 4463
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.143, 1.14
No. of reflections	4844
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.17, −0.34

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

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···S1ⁱ	0.99	2.77	3.469 (2)	128.0
C6—H6A···O1ⁱⁱ	0.99	2.52	3.470 (3)	160.5
C6—H6B···O2ⁱⁱⁱ	0.99	2.51	3.346 (3)	142.5

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

Acknowledgements

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

References

Cattaneo, M. (2009). J. Thromb. Haemost. 7, Suppl. 1, 262–265. Google Scholar
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
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
Wallentin, L. (2009). Eur. Heart J. 30, 1964–1977. Web of Science CrossRef PubMed CAS Google Scholar
Zhi, S., Mu, S., Liu, Y. & Liu, D.-K. (2011). Acta Cryst. E67, o1490. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o2134

doi:10.1107/S1600536811028716

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

2-[4-(4-Methylphenylsulfonyl)piperazin-1-yl]-1-(4,5,6,7-tetra­hydrothieno[3,2-c]pyridin-5-yl)ethanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[4-(4-Methylphenylsulfonyl)piperazin-1-yl]-1-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone