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Volume 69 
Part 8 
Page o1224  
August 2013  

Received 17 June 2013
Accepted 28 June 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.124
Data-to-parameter ratio = 15.3
Details
Open access

2,3-Trimethylene-7,8-dihydropyrrolo[1,2-a]thieno[2,3-d]pyrimidin-4(6H)-one

aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan, and bXinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Science, Urumqi 830011, People's Republic of China
Correspondence e-mail: khurshed-m@mail.ru

The title molecule, C12H12N2OS, is planar, with an r.m.s. deviation of 0.04 Å. In the crystal, the N atom adjacent to the carbonyl group is sp2-hybridized. The crystal structure is stabilized by [pi]-[pi] stacking interactions observed between thiophene and pyrimidinone rings of c-glide-related molecules [centroid-centroid distance = 3.9554 (13) Å] and by C-H...[pi] interactions, forming an infinite chain along the c-axis direction.

Related literature

For background information on related compounds, see: Ibrahim et al. (1996[Ibrahim, Y. A., Elwahy, A. H. M. & Kadry, A. M. (1996). Adv. Heterocycl. Chem. 65, 235-281.]); Litvinov (2004[Litvinov, V. P. (2004). Russ. Chem. Bull. 3, 487-516.]). For the synthesis of the title compound, see: Csukonyi et al. (1986[Csukonyi, K., Lázár, J., Bernáth, G., Hermecz, I. & Mészáros, Z. (1986). Monatsh. Chem. 117, 1295-1303.]); Elmuradov et al. (2011[Elmuradov, B. Zh., Bozorov, Kh. A. & Shakhidoyatov, Kh. M. (2011). Chem. Heterocycl. Compd, 46, 1393-1399.]). For its physiological activity, see: Lilienkampf et al. (2007[Lilienkampf, A., Heikkinen, S., Mutikainen, I. & Wähäla, K. (2007). Synthesis, pp. 2699-2705.]); Moore et al. (2006[Moore, S., Jaeschke, H., Kleinau, G., Neuman, S., Costanzi, S., Jiang, J. K., Childress, J., Raaka, B. M., Colson, A., Paschke, R., Krause, G., Thomas, C. J. & Gershengorn, M. C. (2006). J. Med. Chem. 49, 3888-3896.]). For 1H NMR and IR spectroscopy of the title compound, see: Bozorov et al. (2013[Bozorov, Kh. A., Mamadalieva, N. Z., Elmuradov, B. Zh., Triggiani, D., Egamberdieva, D., Tiezzi, A., Aisa, H. A. & Shakhidoyatov, Kh. M. (2013). J. Chem. article ID 976715, http://dx.doi.org/10.1155/2013/976715 .]). For the related structures of the thieno[2,3-d] pyrimidin-4-one derivatives, see; Lilienkampf et al. (2007[Lilienkampf, A., Heikkinen, S., Mutikainen, I. & Wähäla, K. (2007). Synthesis, pp. 2699-2705.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2OS

  • Mr = 232.30

  • Monoclinic, P 21 /c

  • a = 10.181 (2) Å

  • b = 12.163 (2) Å

  • c = 8.8624 (18) Å

  • [beta] = 100.17 (3)°

  • V = 1080.2 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.48 mm-1

  • T = 292 K

  • 0.20 × 0.17 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.639, Tmax = 0.689

  • 5655 measured reflections

  • 2225 independent reflections

  • 1874 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.124

  • S = 1.06

  • 2225 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1/C2/C3/C3A/C9A (thiophene) and C3A/C4/N5/C8A/N9/C9A rings

D-H...A D-H H...A D...A D-H...A
C6-H6B...Cg2i 0.97 2.85 3.770 (2) 159
C10-H10B...Cg1ii 0.97 2.95 3.735 (2) 139
Symmetry codes: (i) -x, -y+1, -z; (ii) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2490 ).


Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grants FA-F7-T185 and FA-F7-T207), and the project supported by the Funds for International Cooperation and Exchange of the National Natural Science Foundation of China (grant No. 31110103908).

References

Bozorov, Kh. A., Mamadalieva, N. Z., Elmuradov, B. Zh., Triggiani, D., Egamberdieva, D., Tiezzi, A., Aisa, H. A. & Shakhidoyatov, Kh. M. (2013). J. Chem. article ID 976715, http://dx.doi.org/10.1155/2013/976715 .
Csukonyi, K., Lázár, J., Bernáth, G., Hermecz, I. & Mészáros, Z. (1986). Monatsh. Chem. 117, 1295-1303.  [CrossRef] [ChemPort]
Elmuradov, B. Zh., Bozorov, Kh. A. & Shakhidoyatov, Kh. M. (2011). Chem. Heterocycl. Compd, 46, 1393-1399.  [CrossRef] [ChemPort]
Ibrahim, Y. A., Elwahy, A. H. M. & Kadry, A. M. (1996). Adv. Heterocycl. Chem. 65, 235-281.  [CrossRef] [ChemPort]
Lilienkampf, A., Heikkinen, S., Mutikainen, I. & Wähäla, K. (2007). Synthesis, pp. 2699-2705.
Litvinov, V. P. (2004). Russ. Chem. Bull. 3, 487-516.  [Web of Science] [CrossRef]
Moore, S., Jaeschke, H., Kleinau, G., Neuman, S., Costanzi, S., Jiang, J. K., Childress, J., Raaka, B. M., Colson, A., Paschke, R., Krause, G., Thomas, C. J. & Gershengorn, M. C. (2006). J. Med. Chem. 49, 3888-3896.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1224  [ doi:10.1107/S1600536813017935 ]

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