N-(5-Ethylsulfanyl-1,3,4-thiadiazol-2-yl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyri-din-5-yl)acetamide.

In the title compound, C(13)H(16)N(4)OS(3), a thienopyridine-derivative, the tetra-hydro-pyridine ring exhibits a half-chair conformation, and the folded conformation of the mol-ecule is defined by the N-C-C-N torsion angle of -78.85 (16)°. The crystal packing features inter-molecular C-H⋯N, N-H⋯N and C-H⋯O hydrogen bonds.

Related literature

The title compound is a potential anti­platelet agent. As irreversible P2Y12 antagonists, thienopyridines have proved the relevance of inhibiting signaling via the platelet-specific P2Y12 ADP receptor in the prevention of cardiovascular events, see: Iyengar (2009 ▶); Franchini & Mannucci, (2009 ▶); Van Giezen et al. (2009 ▶); Van Giezen & Humphries (2005 ▶). For a related structure, see: Chen et al. (2010 ▶). For the synthesis of the title compound, see: Liu et al. (2008 ▶).

Experimental

Crystal data

C13H16N4OS3

M = 340.48

Monoclinic,

a = 6.532 (4) Å

b = 9.788 (6) Å

c = 23.491 (15) Å

β = 95.524 (6)°

V = 1494.8 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 113 K

0.28 × 0.22 × 0.18 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.873, T max = 0.916

12423 measured reflections

3545 independent reflections

2653 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.03

3545 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.23 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 datablocks global, I. DOI: 10.1107/S1600536811017107/kp2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017107/kp2327Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017107/kp2327Isup3.cdx

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

C13H16N4OS3	F(000) = 712
Mr = 340.48	Dx = 1.513 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4582 reflections
a = 6.532 (4) Å	θ = 1.7–27.9°
b = 9.788 (6) Å	µ = 0.50 mm−1
c = 23.491 (15) Å	T = 113 K
β = 95.524 (6)°	Prism, colourless
V = 1494.8 (16) Å3	0.28 × 0.22 × 0.18 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3545 independent reflections
Radiation source: rotating anode	2653 reflections with I > 2σ(I)
multilayer	Rint = 0.036
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.7°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
Tmin = 0.873, Tmax = 0.916	l = −28→30
12423 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.042P)2] where P = (Fo2 + 2Fc2)/3
3545 reflections	(Δ/σ)max = 0.004
195 parameters	Δρmax = 0.44 e Å−3
1 restraint	Δρmin = −0.23 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	1.09432 (6)	−0.17109 (4)	0.167990 (17)	0.02366 (11)
S2	0.59937 (6)	0.64557 (4)	0.091056 (16)	0.01921 (10)
S3	0.24260 (6)	0.77190 (4)	0.021966 (17)	0.02324 (11)
O1	0.87853 (17)	0.54420 (11)	0.17006 (4)	0.0257 (3)
N1	1.16286 (18)	0.27779 (12)	0.15327 (5)	0.0188 (3)
N2	0.9587 (2)	0.51028 (13)	0.08012 (5)	0.0195 (3)
N3	0.76496 (19)	0.59529 (13)	−0.00107 (5)	0.0199 (3)
N4	0.58266 (19)	0.66332 (13)	−0.01858 (5)	0.0196 (3)
C1	1.3598 (2)	0.20466 (16)	0.15877 (7)	0.0220 (3)
H1A	1.4181	0.2046	0.1993	0.026*
H1B	1.4584	0.2513	0.1359	0.026*
C2	1.3270 (2)	0.05905 (16)	0.13799 (7)	0.0233 (3)
H2A	1.2955	0.0577	0.0959	0.028*
H2B	1.4531	0.0045	0.1479	0.028*
C3	1.1520 (2)	0.00006 (15)	0.16615 (6)	0.0194 (3)
C4	0.8868 (2)	−0.14081 (15)	0.20530 (7)	0.0234 (3)
H4	0.7989	−0.2103	0.2173	0.028*
C5	0.8627 (2)	−0.00627 (15)	0.21566 (6)	0.0214 (3)
H5	0.7562	0.0299	0.2360	0.026*
C6	1.0153 (2)	0.07498 (15)	0.19257 (6)	0.0184 (3)
C7	1.0281 (2)	0.22806 (15)	0.19494 (6)	0.0197 (3)
H7A	0.8889	0.2676	0.1865	0.024*
H7B	1.0824	0.2573	0.2338	0.024*
C8	1.1928 (2)	0.42478 (15)	0.15876 (7)	0.0220 (3)
H8A	1.3052	0.4538	0.1361	0.026*
H8B	1.2324	0.4484	0.1993	0.026*
C9	0.9969 (2)	0.49862 (14)	0.13783 (7)	0.0204 (3)
C10	0.7907 (2)	0.57771 (14)	0.05403 (6)	0.0181 (3)
C11	0.4826 (2)	0.69389 (15)	0.02453 (6)	0.0190 (3)
C12	0.2098 (3)	0.84165 (17)	−0.04979 (7)	0.0300 (4)
H12A	0.3070	0.7958	−0.0734	0.036*
H12B	0.0686	0.8216	−0.0669	0.036*
C13	0.2449 (3)	0.99201 (18)	−0.05141 (8)	0.0362 (4)
H13A	0.1524	1.0379	−0.0271	0.054*
H13B	0.2173	1.0249	−0.0908	0.054*
H13C	0.3879	1.0121	−0.0374	0.054*
H2	1.047 (2)	0.4714 (17)	0.0587 (7)	0.038 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0286 (2)	0.0204 (2)	0.0220 (2)	0.00424 (17)	0.00251 (17)	0.00018 (16)
S2	0.0206 (2)	0.02023 (18)	0.0177 (2)	0.00016 (15)	0.00653 (16)	−0.00083 (15)
S3	0.0217 (2)	0.0242 (2)	0.0244 (2)	0.00316 (16)	0.00550 (17)	0.00097 (16)
O1	0.0338 (7)	0.0255 (6)	0.0190 (6)	0.0047 (5)	0.0095 (5)	0.0034 (5)
N1	0.0177 (7)	0.0200 (6)	0.0189 (7)	0.0010 (5)	0.0038 (5)	0.0011 (5)
N2	0.0192 (7)	0.0222 (6)	0.0178 (7)	0.0017 (5)	0.0052 (5)	−0.0018 (5)
N3	0.0185 (7)	0.0228 (6)	0.0186 (7)	−0.0007 (5)	0.0030 (5)	−0.0029 (5)
N4	0.0179 (7)	0.0210 (6)	0.0200 (7)	−0.0015 (5)	0.0026 (5)	−0.0019 (5)
C1	0.0165 (8)	0.0283 (8)	0.0213 (8)	0.0002 (6)	0.0017 (6)	−0.0002 (6)
C2	0.0190 (8)	0.0286 (8)	0.0224 (8)	0.0039 (7)	0.0031 (7)	−0.0024 (7)
C3	0.0197 (8)	0.0213 (7)	0.0164 (8)	0.0025 (6)	−0.0016 (6)	0.0005 (6)
C4	0.0278 (9)	0.0243 (8)	0.0181 (8)	−0.0009 (7)	0.0020 (7)	0.0045 (6)
C5	0.0235 (8)	0.0252 (8)	0.0157 (8)	0.0019 (6)	0.0031 (6)	0.0020 (6)
C6	0.0198 (8)	0.0210 (7)	0.0141 (7)	0.0014 (6)	−0.0003 (6)	0.0012 (6)
C7	0.0198 (8)	0.0223 (7)	0.0174 (8)	0.0003 (6)	0.0042 (6)	−0.0009 (6)
C8	0.0216 (8)	0.0220 (8)	0.0223 (8)	−0.0037 (6)	0.0020 (7)	0.0002 (6)
C9	0.0248 (8)	0.0154 (7)	0.0216 (8)	−0.0056 (6)	0.0049 (7)	0.0010 (6)
C10	0.0191 (8)	0.0166 (7)	0.0195 (8)	−0.0025 (6)	0.0067 (6)	−0.0013 (6)
C11	0.0193 (8)	0.0176 (7)	0.0200 (8)	−0.0034 (6)	0.0024 (6)	−0.0011 (6)
C12	0.0335 (10)	0.0342 (9)	0.0216 (9)	0.0088 (8)	−0.0004 (7)	−0.0013 (7)
C13	0.0387 (11)	0.0375 (10)	0.0303 (10)	−0.0098 (8)	−0.0067 (8)	0.0095 (8)

S1—C4	1.7096 (18)	C2—H2A	0.9900
S1—C3	1.7186 (18)	C2—H2B	0.9900
S2—C10	1.7232 (16)	C3—C6	1.352 (2)
S2—C11	1.7372 (18)	C4—C5	1.351 (2)
S3—C11	1.7396 (18)	C4—H4	0.9500
S3—C12	1.812 (2)	C5—C6	1.423 (2)
O1—C9	1.2179 (18)	C5—H5	0.9500
N1—C8	1.456 (2)	C6—C7	1.501 (2)
N1—C7	1.4614 (18)	C7—H7A	0.9900
N1—C1	1.467 (2)	C7—H7B	0.9900
N2—C9	1.359 (2)	C8—C9	1.510 (2)
N2—C10	1.373 (2)	C8—H8A	0.9900
N2—H2	0.885 (9)	C8—H8B	0.9900
N3—C10	1.300 (2)	C12—C13	1.490 (3)
N3—N4	1.3914 (18)	C12—H12A	0.9900
N4—C11	1.2921 (19)	C12—H12B	0.9900
C1—C2	1.515 (2)	C13—H13A	0.9800
C1—H1A	0.9900	C13—H13B	0.9800
C1—H1B	0.9900	C13—H13C	0.9800
C2—C3	1.491 (2)
C4—S1—C3	91.75 (7)	C5—C6—C7	125.60 (13)
C10—S2—C11	85.86 (8)	N1—C7—C6	110.02 (11)
C11—S3—C12	102.89 (8)	N1—C7—H7A	109.7
C8—N1—C7	110.75 (11)	C6—C7—H7A	109.7
C8—N1—C1	111.43 (12)	N1—C7—H7B	109.7
C7—N1—C1	110.99 (12)	C6—C7—H7B	109.7
C9—N2—C10	123.21 (13)	H7A—C7—H7B	108.2
C9—N2—H2	117.7 (13)	N1—C8—C9	110.00 (13)
C10—N2—H2	119.1 (13)	N1—C8—H8A	109.7
C10—N3—N4	112.50 (12)	C9—C8—H8A	109.7
C11—N4—N3	111.23 (13)	N1—C8—H8B	109.7
N1—C1—C2	109.60 (13)	C9—C8—H8B	109.7
N1—C1—H1A	109.8	H8A—C8—H8B	108.2
C2—C1—H1A	109.8	O1—C9—N2	121.50 (15)
N1—C1—H1B	109.8	O1—C9—C8	122.81 (15)
C2—C1—H1B	109.8	N2—C9—C8	115.69 (13)
H1A—C1—H1B	108.2	N3—C10—N2	121.95 (13)
C3—C2—C1	108.17 (12)	N3—C10—S2	114.88 (12)
C3—C2—H2A	110.1	N2—C10—S2	123.17 (12)
C1—C2—H2A	110.1	N4—C11—S2	115.51 (12)
C3—C2—H2B	110.1	N4—C11—S3	126.62 (13)
C1—C2—H2B	110.1	S2—C11—S3	117.83 (9)
H2A—C2—H2B	108.4	C13—C12—S3	113.02 (12)
C6—C3—C2	124.21 (14)	C13—C12—H12A	109.0
C6—C3—S1	111.17 (12)	S3—C12—H12A	109.0
C2—C3—S1	124.61 (11)	C13—C12—H12B	109.0
C5—C4—S1	111.89 (12)	S3—C12—H12B	109.0
C5—C4—H4	124.1	H12A—C12—H12B	107.8
S1—C4—H4	124.1	C12—C13—H13A	109.5
C4—C5—C6	112.24 (14)	C12—C13—H13B	109.5
C4—C5—H5	123.9	H13A—C13—H13B	109.5
C6—C5—H5	123.9	C12—C13—H13C	109.5
C3—C6—C5	112.94 (14)	H13A—C13—H13C	109.5
C3—C6—C7	121.45 (13)	H13B—C13—H13C	109.5
C10—N3—N4—C11	0.50 (17)	C7—N1—C8—C9	−70.74 (16)
C8—N1—C1—C2	−165.54 (12)	C1—N1—C8—C9	165.18 (12)
C7—N1—C1—C2	70.53 (16)	C10—N2—C9—O1	2.6 (2)
N1—C1—C2—C3	−49.63 (17)	C10—N2—C9—C8	−178.09 (13)
C1—C2—C3—C6	16.2 (2)	N1—C8—C9—O1	100.49 (17)
C1—C2—C3—S1	−165.28 (12)	N1—C8—C9—N2	−78.85 (16)
C4—S1—C3—C6	−0.65 (13)	N4—N3—C10—N2	178.63 (12)
C4—S1—C3—C2	−179.37 (14)	N4—N3—C10—S2	−1.53 (16)
C3—S1—C4—C5	0.16 (13)	C9—N2—C10—N3	175.29 (14)
S1—C4—C5—C6	0.36 (18)	C9—N2—C10—S2	−4.5 (2)
C2—C3—C6—C5	179.69 (14)	C11—S2—C10—N3	1.57 (12)
S1—C3—C6—C5	0.97 (17)	C11—S2—C10—N2	−178.59 (13)
C2—C3—C6—C7	0.9 (2)	N3—N4—C11—S2	0.73 (16)
S1—C3—C6—C7	−177.84 (12)	N3—N4—C11—S3	−176.86 (10)
C4—C5—C6—C3	−0.9 (2)	C10—S2—C11—N4	−1.29 (12)
C4—C5—C6—C7	177.88 (15)	C10—S2—C11—S3	176.53 (10)
C8—N1—C7—C6	−174.53 (12)	C12—S3—C11—N4	−16.16 (16)
C1—N1—C7—C6	−50.20 (16)	C12—S3—C11—S2	166.30 (9)
C3—C6—C7—N1	15.4 (2)	C11—S3—C12—C13	−103.33 (14)
C5—C6—C7—N1	−163.23 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···N1i	0.99	2.60	3.473 (3)	147
N2—H2···N3ii	0.89 (1)	2.02 (1)	2.902 (2)	171.(2)
C5—H5···O1iii	0.95	2.46	3.279 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯N1i	0.99	2.60	3.473 (3)	147
N2—H2⋯N3ii	0.89 (1)	2.02 (1)	2.902 (2)	171 (2)
C5—H5⋯O1iii	0.95	2.46	3.279 (2)	145

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