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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2762
https://doi.org/10.1107/S1600536810039085

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

Shuai Mu,a Miao Yang,b Deng-Ke Liuc* and Chang-Xiao Liuc

aSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China, bTianjin Medical University, Tianjin 300070, 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 21 September 2010; accepted 30 September 2010; online 9 October 2010)

The title compound, C19H22N4O3S, comprises a thienopyridine moiety which is characteristic for anti­platelet agents of the clopidogrel class of compounds. In the crystal, inversion dimers are formed through pairs of C—H⋯O inter­actions. The benzene ring plane and the nitro plane are almost coplanar, with a dihedral angle of 0.83 (2)°. The piperazine ring adopts a chair conformation.

Related literature

For background to the bioactivity and applications of the anti­platelet agent clopidogrel, see, for example: Muller et al. (2003[Muller, I., Besta, F., Schulz, C., Li, Z., Massberg, S. & Gawaz, M. (2003). Circulation, 108, 2195-2197.]); Savi et al. (1994[Savi, P., Combalbert, J., Gaich, C., Rouchon, M. C., Maffrand, J. P., Berger, Y. & Herbert, J. M. (1994). Thromb. Haemost. 72, 313-317.]); Sharis et al. (1998[Sharis, P. J., Cannon, C. P. & Loscalzo, J. (1998). Ann. Intern. Med. 129, 394-405.]). For the synthesis of other derivatives with thienopyridine, see: Cheng (2009[Cheng, D. (2009). PhD thesis, Tianjin University, China.]).

[Scheme 1]

Experimental

Crystal data

  • C19H22N4O3S

  • Mr = 386.47

  • Triclinic, [P \overline 1]

  • a = 6.1315 (7) Å

  • b = 8.8552 (10) Å

  • c = 17.025 (2) Å

  • α = 84.101 (8)°

  • β = 83.385 (9)°

  • γ = 74.635 (6)°

  • V = 882.87 (18) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 113 K

  • 0.32 × 0.30 × 0.28 mm
Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.935, Tmax = 0.943

  • 10552 measured reflections

  • 4169 independent reflections

  • 3402 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.088

  • S = 1.08

  • 4169 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1⋯O3i 0.95 2.47 3.346 (2) 154
C5—H5A⋯O1ii 0.99 2.56 3.475 (2) 153
C6—H6B⋯O1iii 0.99 2.59 3.420 (2) 142
Symmetry codes: (i) x-1, y+1, z-1; (ii) -x, -y+2, -z; (iii) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXL97; software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810039085/kp2278sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039085/kp2278Isup2.hkl

checkCIF report


Comment top

Clopidogrel is an oral, thienopyridine class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease (Muller et al., 2003; Savi et al., 1994; Sharis et al., 1998). The crystal structure of the title compound (I), a derivative with thienopyridine, synthesised through the transformation of clopidogrel, is reported here.

The C14–C19 benzene ring plane and the nitro plane defined by O2/O3/N4 are almost coplanar, with a dihedral angle of 0.83° (Fig. 1). The piperazine ring shows a stable chair conformation. The bond angle in the ring ranges from 107.24–112.67°. The dihedrals formed between C10–C13 plane and C11/C12/N3 plane, C10–C13 plane and C10/C13/N2 plane are 43.32° and 55.40°, respectively. The packing is realised by C—H···O (Table 1) interactions leading to centrosymmetric dimers.

Related literature top

For background to the bioactivity and applications of the antiplatelet agent clopidogrel, see, for example: Muller et al. (2003); Savi et al. (1994); Sharis et al. (1998). For the synthesis of other derivatives with thienopyridine, see: Cheng (2009).

Experimental top

2-Chloro-1-(4-(4-nitrophenyl)piperazin-1-yl)ethanone 4 g (0.014 mol) and anhydrous K2CO3 7.7 g (0.056 mol) were dissolved in 40 ml toluene. The mixture was heated to 373 K. Then 2.2 g (0.015 mol) of 4,5,6,7-tetrahydrothieno[3,2-c] pyridine was added dropwise into the mixture, and stirred for 16 h under room temperature. K2CO3 was removed after filtration and the reaction solution was concentrated under reduced pressure to get yellow powder as a crude product. The powder was dissolved in a mixture of petroleum ether (20 ml) and acetone (4 ml) at 277 K, then white crystals were grown slowly.

Refinement top

All the H atoms were located on their parent atoms with C—H = 0.95 Å (aromatic CH) and 0.99 Å (CH2), Uiso = 1.2Ueq(C).

Structure description top

Clopidogrel is an oral, thienopyridine class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease (Muller et al., 2003; Savi et al., 1994; Sharis et al., 1998). The crystal structure of the title compound (I), a derivative with thienopyridine, synthesised through the transformation of clopidogrel, is reported here.

The C14–C19 benzene ring plane and the nitro plane defined by O2/O3/N4 are almost coplanar, with a dihedral angle of 0.83° (Fig. 1). The piperazine ring shows a stable chair conformation. The bond angle in the ring ranges from 107.24–112.67°. The dihedrals formed between C10–C13 plane and C11/C12/N3 plane, C10–C13 plane and C10/C13/N2 plane are 43.32° and 55.40°, respectively. The packing is realised by C—H···O (Table 1) interactions leading to centrosymmetric dimers.

For background to the bioactivity and applications of the antiplatelet agent clopidogrel, see, for example: Muller et al. (2003); Savi et al. (1994); Sharis et al. (1998). For the synthesis of other derivatives with thienopyridine, see: Cheng (2009).

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: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), Displacement ellipsoids are drawn at the 50% probability level.
1-[4-(4-Nitrophenyl)piperazin-1-yl]-2-(4,5,6,7- tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone top
Crystal data top
C19H22N4O3SZ = 2
Mr = 386.47F(000) = 408
Triclinic, P1Dx = 1.454 Mg m−3
a = 6.1315 (7) ÅMo Kα radiation, λ = 0.71070 Å
b = 8.8552 (10) ÅCell parameters from 2732 reflections
c = 17.025 (2) Åθ = 1.2–27.9°
α = 84.101 (8)°µ = 0.21 mm−1
β = 83.385 (9)°T = 113 K
γ = 74.635 (6)°Block, yellow
V = 882.87 (18) Å30.32 × 0.30 × 0.28 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		4169 independent reflections
Radiation source: rotating anode3402 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.025
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.2°
ω and φ scansh = −8→8
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		k = −11→11
Tmin = 0.935, Tmax = 0.943l = −22→21
10552 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0455P)2 + 0.1626P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
4169 reflectionsΔρmax = 0.31 e Å−3
245 parametersΔρmin = −0.26 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.019 (7)
Crystal data top
C19H22N4O3Sγ = 74.635 (6)°
Mr = 386.47V = 882.87 (18) Å3
Triclinic, P1Z = 2
a = 6.1315 (7) ÅMo Kα radiation
b = 8.8552 (10) ŵ = 0.21 mm−1
c = 17.025 (2) ÅT = 113 K
α = 84.101 (8)°0.32 × 0.30 × 0.28 mm
β = 83.385 (9)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		4169 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		3402 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.943Rint = 0.025
10552 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.08Δρmax = 0.31 e Å−3
4169 reflectionsΔρmin = −0.26 e Å−3
245 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
xyzUiso*/Ueq
S10.30943 (5)0.92591 (3)−0.249539 (17)0.01923 (11)
O1−0.12392 (14)0.78988 (11)0.05647 (6)0.0249 (2)
O21.01128 (18)0.15750 (13)0.58507 (6)0.0376 (3)
O30.7589 (2)0.02733 (13)0.58411 (7)0.0451 (3)
N10.22099 (16)0.69145 (11)−0.00851 (6)0.0145 (2)
N20.32167 (16)0.71481 (11)0.16167 (6)0.0148 (2)
N30.44060 (16)0.56269 (11)0.31518 (6)0.0156 (2)
N40.8425 (2)0.13723 (14)0.55919 (7)0.0275 (3)
C10.0996 (2)0.85073 (14)−0.27522 (7)0.0208 (3)
H10.03700.8743−0.32490.025*
C20.0340 (2)0.75339 (14)−0.21584 (7)0.0183 (2)
H2−0.08040.7006−0.21930.022*
C30.15476 (19)0.73858 (13)−0.14760 (7)0.0147 (2)
C40.31018 (19)0.82610 (13)−0.15692 (7)0.0147 (2)
C50.45773 (19)0.83687 (14)−0.09431 (7)0.0162 (2)
H5A0.39910.9385−0.07000.019*
H5B0.61480.8302−0.11810.019*
C60.45572 (19)0.70088 (13)−0.03118 (7)0.0156 (2)
H6A0.54670.6011−0.05230.019*
H6B0.52450.71760.01600.019*
C70.1199 (2)0.64098 (14)−0.07174 (7)0.0163 (2)
H7A−0.04460.6535−0.05700.020*
H7B0.19160.5287−0.07920.020*
C80.08392 (19)0.77300 (13)0.04926 (7)0.0161 (2)
C90.1956 (2)0.83986 (14)0.10806 (7)0.0171 (2)
H9A0.30080.89810.07880.021*
H9B0.07750.91470.13960.021*
C100.4469 (2)0.78077 (14)0.21157 (7)0.0173 (2)
H10A0.33870.86070.24330.021*
H10B0.55150.83320.17750.021*
C110.5819 (2)0.65394 (14)0.26673 (7)0.0181 (2)
H11A0.70320.58200.23490.022*
H11B0.65560.70330.30220.022*
C120.2908 (2)0.51145 (14)0.26835 (7)0.0172 (2)
H12A0.18000.46850.30470.021*
H12B0.38240.42630.23580.021*
C130.1640 (2)0.64430 (14)0.21457 (7)0.0177 (2)
H13A0.06970.60390.18260.021*
H13B0.06150.72540.24710.021*
C140.5398 (2)0.45722 (13)0.37518 (7)0.0157 (2)
C150.7310 (2)0.47506 (14)0.40870 (7)0.0194 (3)
H150.79350.56080.38980.023*
C160.8282 (2)0.37062 (15)0.46814 (7)0.0212 (3)
H160.95790.38370.48950.025*
C170.7371 (2)0.24656 (14)0.49676 (7)0.0207 (3)
C180.5485 (2)0.22540 (14)0.46630 (7)0.0214 (3)
H180.48610.14040.48670.026*
C190.4521 (2)0.32864 (14)0.40612 (7)0.0194 (3)
H190.32370.31310.38490.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02648 (18)0.01618 (16)0.01532 (16)−0.00697 (12)−0.00135 (12)0.00086 (11)
O10.0145 (4)0.0317 (5)0.0297 (5)−0.0068 (4)0.0002 (4)−0.0080 (4)
O20.0329 (6)0.0445 (6)0.0350 (6)−0.0089 (5)−0.0162 (5)0.0104 (5)
O30.0627 (8)0.0347 (6)0.0444 (7)−0.0234 (6)−0.0272 (6)0.0207 (5)
N10.0127 (5)0.0165 (5)0.0148 (5)−0.0046 (4)−0.0031 (4)0.0004 (4)
N20.0149 (5)0.0158 (5)0.0154 (5)−0.0068 (4)−0.0027 (4)0.0006 (4)
N30.0160 (5)0.0161 (5)0.0164 (5)−0.0074 (4)−0.0027 (4)0.0005 (4)
N40.0324 (6)0.0252 (6)0.0230 (6)−0.0035 (5)−0.0069 (5)0.0023 (5)
C10.0269 (6)0.0191 (6)0.0169 (6)−0.0045 (5)−0.0062 (5)−0.0025 (5)
C20.0210 (6)0.0172 (5)0.0179 (6)−0.0049 (5)−0.0042 (5)−0.0045 (5)
C30.0148 (5)0.0117 (5)0.0166 (6)−0.0014 (4)−0.0016 (4)−0.0022 (4)
C40.0162 (5)0.0121 (5)0.0148 (5)−0.0021 (4)−0.0010 (4)−0.0009 (4)
C50.0141 (5)0.0165 (5)0.0187 (6)−0.0057 (4)−0.0020 (5)0.0008 (4)
C60.0116 (5)0.0170 (5)0.0178 (6)−0.0029 (4)−0.0033 (4)0.0013 (4)
C70.0182 (6)0.0163 (5)0.0163 (6)−0.0071 (4)−0.0048 (5)0.0006 (4)
C80.0167 (6)0.0136 (5)0.0178 (6)−0.0040 (4)−0.0037 (5)0.0020 (4)
C90.0185 (6)0.0149 (5)0.0184 (6)−0.0048 (4)−0.0021 (5)−0.0011 (4)
C100.0191 (6)0.0174 (5)0.0183 (6)−0.0092 (5)−0.0036 (5)−0.0006 (5)
C110.0168 (6)0.0203 (6)0.0199 (6)−0.0101 (5)−0.0026 (5)0.0008 (5)
C120.0171 (6)0.0182 (6)0.0191 (6)−0.0096 (5)−0.0036 (5)0.0010 (5)
C130.0144 (5)0.0198 (6)0.0202 (6)−0.0075 (4)−0.0016 (5)0.0004 (5)
C140.0166 (5)0.0151 (5)0.0148 (5)−0.0033 (4)0.0017 (4)−0.0037 (4)
C150.0205 (6)0.0202 (6)0.0191 (6)−0.0076 (5)−0.0021 (5)−0.0024 (5)
C160.0208 (6)0.0236 (6)0.0203 (6)−0.0060 (5)−0.0042 (5)−0.0039 (5)
C170.0245 (6)0.0190 (6)0.0162 (6)−0.0012 (5)−0.0023 (5)−0.0010 (5)
C180.0264 (7)0.0175 (6)0.0204 (6)−0.0069 (5)−0.0003 (5)−0.0003 (5)
C190.0204 (6)0.0190 (6)0.0199 (6)−0.0070 (5)−0.0025 (5)−0.0015 (5)
Geometric parameters (Å, º) top
S1—C11.7127 (13)C6—H6B0.9900
S1—C41.7265 (12)C7—H7A0.9900
O1—C81.2362 (14)C7—H7B0.9900
O2—N41.2317 (16)C8—C91.5219 (16)
O3—N41.2327 (16)C9—H9A0.9900
N1—C81.3524 (16)C9—H9B0.9900
N1—C71.4638 (14)C10—C111.5160 (16)
N1—C61.4685 (14)C10—H10A0.9900
N2—C131.4628 (14)C10—H10B0.9900
N2—C101.4637 (14)C11—H11A0.9900
N2—C91.4690 (15)C11—H11B0.9900
N3—C141.3900 (15)C12—C131.5115 (16)
N3—C121.4662 (14)C12—H12A0.9900
N3—C111.4674 (14)C12—H12B0.9900
N4—C171.4491 (16)C13—H13A0.9900
C1—C21.3558 (18)C13—H13B0.9900
C1—H10.9500C14—C151.4125 (17)
C2—C31.4251 (16)C14—C191.4140 (16)
C2—H20.9500C15—C161.3746 (17)
C3—C41.3658 (16)C15—H150.9500
C3—C71.5051 (16)C16—C171.3818 (18)
C4—C51.5008 (16)C16—H160.9500
C5—C61.5311 (16)C17—C181.3833 (18)
C5—H5A0.9900C18—C191.3768 (17)
C5—H5B0.9900C18—H180.9500
C6—H6A0.9900C19—H190.9500
C1—S1—C492.11 (6)N2—C9—H9A109.4
C8—N1—C7119.36 (10)C8—C9—H9A109.4
C8—N1—C6123.35 (10)N2—C9—H9B109.4
C7—N1—C6113.03 (9)C8—C9—H9B109.4
C13—N2—C10107.24 (9)H9A—C9—H9B108.0
C13—N2—C9110.12 (9)N2—C10—C11111.11 (9)
C10—N2—C9109.88 (9)N2—C10—H10A109.4
C14—N3—C12117.17 (9)C11—C10—H10A109.4
C14—N3—C11117.63 (9)N2—C10—H10B109.4
C12—N3—C11112.57 (9)C11—C10—H10B109.4
O2—N4—O3122.75 (11)H10A—C10—H10B108.0
O2—N4—C17118.95 (11)N3—C11—C10112.67 (10)
O3—N4—C17118.30 (11)N3—C11—H11A109.1
C2—C1—S1111.59 (9)C10—C11—H11A109.1
C2—C1—H1124.2N3—C11—H11B109.1
S1—C1—H1124.2C10—C11—H11B109.1
C1—C2—C3112.85 (11)H11A—C11—H11B107.8
C1—C2—H2123.6N3—C12—C13112.06 (9)
C3—C2—H2123.6N3—C12—H12A109.2
C4—C3—C2112.58 (11)C13—C12—H12A109.2
C4—C3—C7121.64 (10)N3—C12—H12B109.2
C2—C3—C7125.77 (10)C13—C12—H12B109.2
C3—C4—C5124.49 (11)H12A—C12—H12B107.9
C3—C4—S1110.87 (9)N2—C13—C12110.96 (9)
C5—C4—S1124.63 (9)N2—C13—H13A109.4
C4—C5—C6108.25 (9)C12—C13—H13A109.4
C4—C5—H5A110.0N2—C13—H13B109.4
C6—C5—H5A110.0C12—C13—H13B109.4
C4—C5—H5B110.0H13A—C13—H13B108.0
C6—C5—H5B110.0N3—C14—C15121.43 (11)
H5A—C5—H5B108.4N3—C14—C19121.51 (11)
N1—C6—C5109.67 (9)C15—C14—C19117.06 (11)
N1—C6—H6A109.7C16—C15—C14121.21 (11)
C5—C6—H6A109.7C16—C15—H15119.4
N1—C6—H6B109.7C14—C15—H15119.4
C5—C6—H6B109.7C15—C16—C17119.90 (12)
H6A—C6—H6B108.2C15—C16—H16120.0
N1—C7—C3109.44 (9)C17—C16—H16120.0
N1—C7—H7A109.8C16—C17—C18120.89 (12)
C3—C7—H7A109.8C16—C17—N4119.13 (12)
N1—C7—H7B109.8C18—C17—N4119.98 (11)
C3—C7—H7B109.8C19—C18—C17119.43 (11)
H7A—C7—H7B108.2C19—C18—H18120.3
O1—C8—N1122.19 (11)C17—C18—H18120.3
O1—C8—C9120.27 (11)C18—C19—C14121.51 (11)
N1—C8—C9117.51 (10)C18—C19—H19119.2
N2—C9—C8111.26 (9)C14—C19—H19119.2
C4—S1—C1—C2−0.24 (10)C9—N2—C10—C11−179.10 (9)
S1—C1—C2—C30.11 (14)C14—N3—C11—C10−171.71 (10)
C1—C2—C3—C40.12 (15)C12—N3—C11—C1047.41 (13)
C1—C2—C3—C7179.31 (11)N2—C10—C11—N3−54.79 (13)
C2—C3—C4—C5178.37 (10)C14—N3—C12—C13170.61 (10)
C7—C3—C4—C5−0.85 (17)C11—N3—C12—C13−48.32 (13)
C2—C3—C4—S1−0.30 (13)C10—N2—C13—C12−62.45 (12)
C7—C3—C4—S1−179.52 (9)C9—N2—C13—C12178.02 (9)
C1—S1—C4—C30.31 (9)N3—C12—C13—N256.93 (13)
C1—S1—C4—C5−178.36 (10)C12—N3—C14—C15162.26 (10)
C3—C4—C5—C616.48 (15)C11—N3—C14—C1523.17 (16)
S1—C4—C5—C6−165.03 (8)C12—N3—C14—C19−18.64 (16)
C8—N1—C6—C5−87.64 (13)C11—N3—C14—C19−157.73 (11)
C7—N1—C6—C568.93 (12)N3—C14—C15—C16179.86 (11)
C4—C5—C6—N1−47.59 (12)C19—C14—C15—C160.72 (18)
C8—N1—C7—C3107.55 (12)C14—C15—C16—C17−0.80 (19)
C6—N1—C7—C3−50.05 (12)C15—C16—C17—C180.11 (19)
C4—C3—C7—N116.24 (15)C15—C16—C17—N4179.73 (11)
C2—C3—C7—N1−162.88 (11)O2—N4—C17—C16−0.17 (18)
C7—N1—C8—O19.29 (17)O3—N4—C17—C16179.92 (13)
C6—N1—C8—O1164.47 (11)O2—N4—C17—C18179.45 (12)
C7—N1—C8—C9−172.84 (9)O3—N4—C17—C18−0.46 (19)
C6—N1—C8—C9−17.67 (16)C16—C17—C18—C190.64 (19)
C13—N2—C9—C8−68.22 (12)N4—C17—C18—C19−178.97 (11)
C10—N2—C9—C8173.88 (9)C17—C18—C19—C14−0.72 (19)
O1—C8—C9—N2106.91 (12)N3—C14—C19—C18−179.10 (11)
N1—C8—C9—N2−71.00 (13)C15—C14—C19—C180.05 (18)
C13—N2—C10—C1161.22 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O3i0.952.473.346 (2)154
C5—H5A···O1ii0.992.563.475 (2)153
C6—H6B···O1iii0.992.593.420 (2)142
Symmetry codes: (i) x−1, y+1, z−1; (ii) −x, −y+2, −z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC19H22N4O3S
Mr386.47
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)6.1315 (7), 8.8552 (10), 17.025 (2)
α, β, γ (°)84.101 (8), 83.385 (9), 74.635 (6)
V (Å3)882.87 (18)
Z2
Radiation typeMo Kα
µ (mm−1)0.21
Crystal size (mm)0.32 × 0.30 × 0.28
Data collection
DiffractometerRigaku Saturn CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.935, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections		10552, 4169, 3402
Rint0.025
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.088, 1.08
No. of reflections4169
No. of parameters245
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.31, −0.26

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O3i0.952.473.346 (2)154.0
C5—H5A···O1ii0.992.563.475 (2)153.0
C6—H6B···O1iii0.992.593.420 (2)142.0
Symmetry codes: (i) x−1, y+1, z−1; (ii) −x, −y+2, −z; (iii) x+1, y, z.
 

Acknowledgements

The authors thank Mr Hai-Bin Song of Nankai University and Mr Zhi-Qiang Cai of Tianjin Institute of Pharmaceutical Research for their helpful suggestions.

References

First citationCheng, D. (2009). PhD thesis, Tianjin University, China.  Google Scholar
 First citationMuller, I., Besta, F., Schulz, C., Li, Z., Massberg, S. & Gawaz, M. (2003). Circulation, 108, 2195–2197.  Web of Science CrossRef PubMed Google Scholar
 First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSavi, P., Combalbert, J., Gaich, C., Rouchon, M. C., Maffrand, J. P., Berger, Y. & Herbert, J. M. (1994). Thromb. Haemost. 72, 313–317.  CAS PubMed Web of Science Google Scholar
 First citationSharis, P. J., Cannon, C. P. & Loscalzo, J. (1998). Ann. Intern. Med. 129, 394–405.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2762
https://doi.org/10.1107/S1600536810039085
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