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Volume 68 
Part 11 
Pages o3092-o3093  
November 2012  

Received 15 September 2012
Accepted 29 September 2012
Online 10 October 2012

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.080
Data-to-parameter ratio = 19.0
Details
Open access

rac-Ethyl 4-hydroxy-4-trifluoromethyl-6-(2,4,5-trimethoxyphenyl)-2-thio-1,3-diazinane-5-carboxylate

aState Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province, 461000, People's Republic of China
Correspondence e-mail: chinarenbeijing@126.com

In the title compound, C17H21F3N2O6S, the hexahydropyrimidine ring adopts a half-chair conformation: the mean plane formed by the ring atoms excluding the C atom bonded to the ethoxycarbonyl group has an r.m.s. deviation of 0.0427 Å and forms a dihedral angle of 66.41 (5)° with the benzene ring. The molecular conformation is stabilized by an intramolecular hydroxyl O-H...Ocarboxyl hydrogen bond, generating an S(6) ring. In the crystal, pairs of N-H...S and N-H...O hydrogen bonds give rise to the formation of two-dimensional networks lying parallel to the ab plane, which incorporate graph-set motifs R22(8) and R22(16), respectively.

Related literature

For the bioactivity of dihydropyrimidines, see: Brier et al. (2004[Brier, S., Lemaire, D., Debonis, S., Forest, E. & Kozielski, F. (2004). Biochemistry, 43, 13072-13082.]); Cochran et al. (2005[Cochran, J. C., Gatial, J. E., Kapoor, T. M. & Gilbert, S. P. (2005). J. Biol. Chem. 280, 12658-12667.]); Moran et al. (2007[Moran, M. M., Fanger, C., Chong, J. A., Mcnamara, C., Zhen, X. G. & Mandel-Brehm, J. (2007). WO Patent No. 2 007 073 505.]); Zorkun et al. (2006[Zorkun, I. S., Sarac, S., Celebi, S. & Erol, K. (2006). Bioorg. Med. Chem. 14, 8582-8589.]) and for the bioactivity of organofluorine compounds, see: Hermann et al. (2003[Hermann, B., Erwin, H. & Hansjorg, K. (2003). US patent No. 2 003 176 284.]); Ulrich (2004[Ulrich, H. (2004). US patent No. 2 004 033 897.]). For the original Biginelli synthesis, see: Biginelli (1893[Biginelli, P. (1893). Gazz. Chim. Ital. 23, 360-413.]). For a related structure, see: Li et al. (2011[Li, G.-C., Wu, C.-Z., Guo, L.-L. & Yang, F.-L. (2011). Acta Cryst. E67, o1704-o1705.]). For graph-set analysis, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C17H21F3N2O6S

  • Mr = 438.42

  • Triclinic, [P \overline 1]

  • a = 9.5070 (8) Å

  • b = 9.9040 (8) Å

  • c = 11.4710 (13) Å

  • [alpha] = 71.582 (13)°

  • [beta] = 76.740 (16)°

  • [gamma] = 79.743 (15)°

  • V = 990.89 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 113 K

  • 0.28 × 0.22 × 0.20 mm

Data collection
  • Rigaku Saturn724 CCD-detector diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998)[Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.] Tmin = 0.939, Tmax = 0.956

  • 13891 measured reflections

  • 5290 independent reflections

  • 3175 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.080

  • S = 0.90

  • 5290 reflections

  • 279 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 0.820 (15) 2.103 (16) 2.8055 (15) 143.5 (15)
N2-H2...O5i 0.824 (15) 2.129 (15) 2.9521 (15) 176.6 (15)
N1-H1A...S1ii 0.834 (15) 2.526 (16) 3.3427 (13) 166.3 (15)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalClear and CrystalStructure. Rigaku/MSC, 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: CrystalStructure (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2236 ).


Acknowledgements

The authors thank the Technology Research and Development Program of Henan Province, China (grant No. 122102210426).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Biginelli, P. (1893). Gazz. Chim. Ital. 23, 360-413.
Brier, S., Lemaire, D., Debonis, S., Forest, E. & Kozielski, F. (2004). Biochemistry, 43, 13072-13082.  [ISI] [CrossRef] [PubMed] [ChemPort]
Cochran, J. C., Gatial, J. E., Kapoor, T. M. & Gilbert, S. P. (2005). J. Biol. Chem. 280, 12658-12667.  [CrossRef] [PubMed] [ChemPort]
Hermann, B., Erwin, H. & Hansjorg, K. (2003). US patent No. 2 003 176 284.
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.
Li, G.-C., Wu, C.-Z., Guo, L.-L. & Yang, F.-L. (2011). Acta Cryst. E67, o1704-o1705.  [CSD] [CrossRef] [details]
Moran, M. M., Fanger, C., Chong, J. A., Mcnamara, C., Zhen, X. G. & Mandel-Brehm, J. (2007). WO Patent No. 2 007 073 505.
Rigaku/MSC (2009). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Ulrich, H. (2004). US patent No. 2 004 033 897.
Zorkun, I. S., Sarac, S., Celebi, S. & Erol, K. (2006). Bioorg. Med. Chem. 14, 8582-8589.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3092-o3093   [ doi:10.1107/S1600536812041013 ]

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