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

Li, Y.-Q.; Ju, Z.-Y.

doi:10.1107/S1600536812041013

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 (C-C) = 0.002 Å
R = 0.033
wR = 0.080
Data-to-parameter ratio = 19.0
Details

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

Yong-Qiang Li ^a ^* and Zhi-Yu Ju ^b

^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-HO_carboxyl hydrogen bond, generating an S(6) ring. In the crystal, pairs of N-HS and N-HO 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); Cochran et al. (2005); Moran et al. (2007); Zorkun et al. (2006) and for the bioactivity of organofluorine compounds, see: Hermann et al. (2003); Ulrich (2004). For the original Biginelli synthesis, see: Biginelli (1893). For a related structure, see: Li et al. (2011). For graph-set analysis, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₇H₂₁F₃N₂O₆S
M_r = 438.42
Triclinic, $[P \overline 1]$
a = 9.5070 (8) Å
b = 9.9040 (8) Å
c = 11.4710 (13) Å
= 71.582 (13)°
= 76.740 (16)°
= 79.743 (15)°
V = 990.89 (19) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.939, T_max = 0.956
13891 measured reflections
5290 independent reflections
3175 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(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
_max = 0.33 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2	0.820 (15)	2.103 (16)	2.8055 (15)	143.5 (15)
N2-H2O5ⁱ	0.824 (15)	2.129 (15)	2.9521 (15)	176.6 (15)
N1-H1AS1ⁱⁱ	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); 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: CrystalStructure (Rigaku/MSC, 2009); 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.
Biginelli, P. (1893). Gazz. Chim. Ital. 23, 360-413.
Brier, S., Lemaire, D., Debonis, S., Forest, E. & Kozielski, F. (2004). Biochemistry, 43, 13072-13082.
Cochran, J. C., Gatial, J. E., Kapoor, T. M. & Gilbert, S. P. (2005). J. Biol. Chem. 280, 12658-12667.
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.
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.
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.

organic compounds