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

Zhi, S.; Mu, S.; Liu, Y.; Liu, D.-K.

doi:10.1107/S1600536811017107

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1490

doi:10.1107/S1600536811017107

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

Shuang Zhi,^a Shuai Mu,^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, ^bSchool of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People's Republic of China, and ^cTianjin Institute of Pharmaceutical Research, Tianjin, 300193, People's Republic of China
^*Correspondence e-mail: liudk@tjipr.com

(Received 4 May 2011; accepted 6 May 2011; online 25 May 2011)

In the title compound, C₁₃H₁₆N₄OS₃, a thienopyridinederivative, the tetrahydropyridine ring exhibits a half-chair conformation, and the folded conformation of the molecule is defined by the N—C—C—N torsion angle of −78.85 (16)°. The crystal packing features intermolecular 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_r = 340.48
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.079
S = 1.03
3545 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) -x+1, -y+1, -z; (ii) -x+2, -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/S1600536811017107/kp2327sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811017107/kp2327Isup3.cdx

checkCIF report

Comment top

As irreversible P2Y12 antagonists, the thienopyridines (e.g., clopidogrel and prasugrel) have been further proved the relevance of inhibiting signaling via the platelet-specific P2Y12 ADP receptor in the prevention of cardiovascular events (Iyengar, 2009; Van Giezen & Humphries, 2005; Franchini, et al., 2009). The structure of the title compound (I), a new derivative of thienopyridine, is presented here.

The tetrahydropyridine ring is in a half-chair conformation (Fig. 1). The thiadiazole ring plane (r.m.s. deviation 0.0020Å) and the acidamide plane (r.m.s. deviation 0.0074 Å) are almost coplanar, with a dihedral angle of 3.24 (9)°. The dihedral angles formed between the thiadiazole ring plane and the thiophene ring plane, the acidamide plane and the thiophene ring plane are 76.19 (6)° and 78.47 (7)° , respectively. Crystal packing is via hydrogen bonds C—H···N, N—H···N and C—H···O (Table 1, Fig. 2).

Related literature top

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 top

Chloracetyl chloride was dropwised added into a mixture of 5-(ethylthio)-1,3,4-thiadiazol-2-amine, TEA and DMF at 268 K. After stirred for 3 h, the mixture was poured into cold water. 2-Chloro-N-(5-(ethylthio)-1,3,4-thiadiazol-2-yl)acetamide was precipitated as an intermediate. Then the intermediate, equimolar quantities thienopyridine salt and TEA were refluxed for 5 h in acetonitrile, and the product was obtained by silica gel column chromatography. Crystallisation of the obtained yellow solid from methanol afforded light-yellow crystals suitable 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.

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

Crystal data top

C₁₃H₁₆N₄OS₃	F(000) = 712
M_r = 340.48	D_x = 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

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3545 independent reflections
Radiation source: rotating anode	2653 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.036
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω and ϕ scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
T_min = 0.873, T_max = 0.916	l = −28→30
12423 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)] = 0.030	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(F_o²) + (0.042P)²] where P = (F_o² + 2F_c²)/3
3545 reflections	(Δ/σ)_max = 0.004
195 parameters	Δρ_max = 0.44 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₃H₁₆N₄OS₃	V = 1494.8 (16) Å³
M_r = 340.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.532 (4) Å	µ = 0.50 mm⁻¹
b = 9.788 (6) Å	T = 113 K
c = 23.491 (15) Å	0.28 × 0.22 × 0.18 mm
β = 95.524 (6)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3545 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2653 reflections with I > 2σ(I)
T_min = 0.873, T_max = 0.916	R_int = 0.036
12423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.44 e Å⁻³
3545 reflections	Δρ_min = −0.23 e Å⁻³
195 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	1.09432 (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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₄OS₃
M_r	340.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	6.532 (4), 9.788 (6), 23.491 (15)
β (°)	95.524 (6)
V (Å³)	1494.8 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.873, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections	12423, 3545, 2653
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.079, 1.03
No. of reflections	3545
No. of parameters	195
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.23

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
C12—H12B···N1ⁱ	0.99	2.60	3.473 (3)	147
N2—H2···N3ⁱⁱ	0.885 (9)	2.023 (10)	2.902 (2)	171.4 (18)
C5—H5···O1ⁱⁱⁱ	0.95	2.46	3.279 (2)	145

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

Chen, J.-F., Liu, Y., Wang, J.-Y. & Liu, D.-K. (2010). Acta Cryst. E66, o3213. Web of Science CSD CrossRef IUCr Journals Google Scholar
Franchini, M. & Mannucci, P. M. (2009). Eur. J. Int. Med. 20, 733–738. CrossRef CAS Google Scholar
Iyengar, S. (2009). J. Thromb. Thrombolysis, 27, 300–306. Web of Science CrossRef PubMed CAS 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
Van Giezen, J. J. J., Berntsson, P., Zachrisson, H. & Bjorkman, J. A. (2009). Thromb. Res. 124, 565–571. Web of Science CrossRef PubMed CAS Google Scholar
Van Giezen, J. J. J. & Humphries, R. G. (2005). Sem. Thromb. Hemost. 31, 195–204. CrossRef CAS Google Scholar

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Volume 67| Part 6| June 2011| Page o1490

doi:10.1107/S1600536811017107

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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