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

In the title thienopyridine derivative, C(20)H(25)N(3)O(3)S(2), the piperazine ring exhibits a chair conformation and the tetra-hydro-pyridine ring exhibits a half-chair conformation. The folded conformation of the mol-ecule is defined by the N-C-C-N torsion angle of -70.20 (2) °. Inter-molecular 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 = 419.55

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.143

S = 1.14

4844 reflections

254 parameters

H-atom parameters constrained

Δρmax = 1.17 e Å−3

Δρmin = −0.34 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/S1600536811028716/fl2350sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811028716/fl2350Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811028716/fl2350Isup4.cml

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

C20H25N3O3S2	F(000) = 1776
Mr = 419.55	Dx = 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

Rigaku Saturn CCD area-detector diffractometer	4844 independent reflections
Radiation source: rotating anode	4463 reflections with I > 2σ(I)
multilayer	Rint = 0.054
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.1°
ω and φ scans	h = −17→17
Absorption correction: multi-scan CrystalClear	k = −20→20
Tmin = 0.934, Tmax = 0.950	l = −26→25
49454 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0665P)2 + 2.3859P] where P = (Fo2 + 2Fc2)/3
4844 reflections	(Δ/σ)max = 0.002
254 parameters	Δρmax = 1.17 e Å−3
0 restraints	Δρmin = −0.34 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	−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*

	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)

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)

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.

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) ; (ii) ; (iii) .