Ethyl 6-(4-fluoro­phen­yl)-4-hy­droxy-2-oxo-4-trifluoro­meth­yl-1,3-diazinane-5-carboxyl­ate monohydrate

Li, G.-C.; Wu, C.-Z.; Guo, L.-L.; Yang, F.-L.

doi:10.1107/S1600536811021866

Volume 67
Part 7
Pages o1704-o1705
July 2011

Received 22 May 2011
Accepted 7 June 2011
Online 18 June 2011

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.072
Data-to-parameter ratio = 15.4
Details

Ethyl 6-(4-fluorophenyl)-4-hydroxy-2-oxo-4-trifluoromethyl-1,3-diazinane-5-carboxylate monohydrate

Gong-Chun Li,^a Chang-Zeng Wu,^a Li-Li Guo ^b and Feng-Ling Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China, and ^bDepartment of Chemistry, Zhengzhou University, Zhengzhou Henan Province, 450052, People's Republic of China
Correspondence e-mail: actaeli@gmail.com

The asymmetric unit of the title compound, C₁₄H₁₄F₄N₂O₄·H₂O, contains two crystallographically independent organic molecules and two water molecules. The two 1,3-diazinane rings adopt a half-chair conformation and the dihedral angles between their mean planes and those of the benzene rings are 75.65 (4)° and 49.41 (3)° in the two molecules. The crystal structure is stabilized by intermolecular O-HO and N-HO hydrogen bonds.

Related literature

For the bioactivity of dihydropyrimidines, see: Brier et al. (2004); Cochran et al. (2005); Moran et al. (2007); Zorkun et al. (2006). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003); Ulrich (2004). For a related structure, see: Song et al. (2010).

Experimental

Crystal data

C₁₄H₁₄F₄N₂O₄·H₂O
M_r = 368.29
Triclinic, $[P \overline 1]$
a = 10.0196 (9) Å
b = 12.1718 (12) Å
c = 14.3037 (14) Å
= 98.463 (7)°
= 103.642 (8)°
= 104.400 (9)°
V = 1602.2 (3) Å³
Z = 4
Mo K radiation
= 0.14 mm^-1
T = 113 K
0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009) T_min = 0.972, T_max = 0.980
20692 measured reflections
7612 independent reflections
4575 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.072
S = 0.87
7612 reflections
493 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O9ⁱ	0.889 (15)	1.860 (16)	2.7482 (14)	176.2 (15)
O9-H9AO3ⁱⁱ	0.91 (2)	1.90 (2)	2.8026 (15)	169.8 (18)
O6-H6O10ⁱⁱⁱ	0.893 (16)	1.788 (16)	2.6770 (14)	173.5 (15)
N3-H3AO10ⁱⁱⁱ	0.823 (14)	2.583 (15)	3.0737 (16)	119.6 (12)
N4-H4AO5ⁱⁱⁱ	0.904 (14)	1.900 (15)	2.8010 (14)	174.8 (13)
N1-H1AO1^iv	0.828 (14)	2.109 (14)	2.9235 (15)	167.9 (13)
N2-H2AO5^v	0.906 (14)	1.958 (15)	2.8395 (14)	163.8 (13)
O9-H9BO1^vi	0.80 (2)	2.00 (2)	2.7443 (15)	155 (2)
O10-H10AO9^vii	0.861 (17)	1.925 (17)	2.7833 (15)	175.4 (16)
O10-H10BO7^viii	0.82 (2)	2.07 (2)	2.8685 (14)	166 (2)
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+2, -z+2; (iv) -x+1, -y, -z+1; (v) -x+1, -y+1, -z+2; (vi) -x+1, -y+1, -z+1; (vii) -x+1, -y+2, -z+1; (viii) x+1, y, z.

Data collection: CrystalClear (Rigaku, 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2293 ).

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province, China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Education Department, China (grant No. 2007150036).

References

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 2 003 176 284.
Moran, M. M., Fanger, C., Chong, J. A., McNamara, C., Zhen, X. G. & Mandel-Brehm, J. (2007). WO Patent 2 007 073 505.
Rigaku (2009). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, X.-P., Li, G.-C., Wu, C.-Z. & Yang, F.-L. (2010). Acta Cryst. E66, o1083.
Ulrich, H. (2004). US patent 2 004 033 897.
Zorkun, I. S., Sarac, S., Celebi, S. & Erol, K. (2006). Bioorg. Med. Chem. 14, 8582-8589.

organic compounds