2-Methyl-4-oxo-6,7,8,9-tetrahydro­thieno[2′,3′:4,5]pyrimidino­[1,2-a]pyridine-3-carboxylic acid

Elmuradov, B.Z.; Bozorov, K.A.; Okmanov, R.Y.; Tashkhodjaev, B.; Shakhidoyatov, K.M.

doi:10.1107/S1600536811007902

Volume 67
Part 4
Page o824
April 2011

Received 17 January 2011
Accepted 2 March 2011
Online 9 March 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R = 0.063
wR = 0.169
Data-to-parameter ratio = 9.9
Details

2-Methyl-4-oxo-6,7,8,9-tetrahydrothieno[2',3':4,5]pyrimidino[1,2-a]pyridine-3-carboxylic acid

Burkhon Zh. Elmuradov,^a ^* Khurshed A. Bozorov,^a Rasul Ya. Okmanov,^a Bakhodir Tashkhodjaev ^a and Khusnutdin M. Shakhidoyatov ^a

^aS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek St 77, Tashkent 100170, Uzbekistan
Correspondence e-mail: burkhon@rambler.ru

There are two independent molecules in the asymmetric unit of the title compound, C₁₂H₁₂N₂O₃S. With the exception of the methylene groups, a mean plane fitted through all non-H atoms of each molecule has an r.m.s. deviation of 0.035 Å for one molecule and 0.120 Å for the second. In one of the independent molecules, the methylene groups was refined using a disorder model with an occupancy ratio of 0.53:0.47 (14). Each molecule features an intramolecular O-HO hydrogen bond, which generates an S(7) ring.

Related literature

For the synthesis of thieno[2,3-d]pyrimidin-4-ones and their derivatives, see: Litvinov (2004); Elmuradov et al. (2010); Csukonyi et al. (1986). For the physiological activity of thieno[2,3-d]pyrimidin-4-ones and their derivatives, see: Lilienkampf et al. (2007). For a related structure, see: Bozorov et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₂H₁₂N₂O₃S
M_r = 264.30
Monoclinic, P 2₁ /n
a = 7.2550 (15) Å
b = 20.506 (4) Å
c = 15.824 (3) Å
= 96.93 (3)°
V = 2337.0 (8) Å³
Z = 8
Cu K radiation
= 2.50 mm^-1
T = 296 K
0.60 × 0.40 × 0.15 mm

Data collection

Stoe STADI4 diffractometer
Absorption correction: scan (Blessing, 1987) T_min = 0.346, T_max = 0.687
4297 measured reflections
3438 independent reflections
2420 reflections with I > 2(I)
R_int = 0.047
_max = 60.0°
3 standard reflections every 60 min intensity decay: 4.7%

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.169
S = 1.10
3438 reflections
348 parameters
23 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2OO1	0.87 (2)	1.63 (2)	2.501 (5)	177 (7)
O52-H52OO51	0.87 (2)	1.71 (3)	2.518 (6)	154 (4)

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997); 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: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2082 ).

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grants FA-F3-T045 and FA-F3-T047)

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Blessing, R. H. (1987). Crystallogr. Rev. 1, 3-58.
Bozorov, K. A., Elmuradov, B. Z., Okmanov, R. Y., Tashkhodjaev, B. & Shakhidoyatov, K. M. (2010). Acta Cryst. E66, o552-o553.
Csukonyi, K., Lazar, J., Bernath, G., Hermecz, I. & Meszaros, Z. (1986). Monatsh. Chem. 117, 1295-1303.
Elmuradov, B. Zh., Bozorov, Kh. A. & Shakhidoyatov, Kh. M. (2010). Khim. Get. Soedin. pp. 1717-1724.
Lilienkampf, A., Heikkinen, S., Mutikainen, I. & Wähäla, K. (2007). Synthesis, pp. 2699-2705.
Litvinov, V. P. (2004). Izv. Akad. Nauk. Ser. Khim. 3, 463-490.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (1997). STADI4 and X-RED. Stoe & Cie, Darmstadt, Germany.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds