N-Cyclo­propyl-N-[2-(2,4-difluoro­phen­yl)-2-hy­droxy-1-(1H-1,2,4-triazol-1-yl)prop­yl]-2-(5-methyl-2,4-dioxo-1,2,3,4-tetra­hydro­pyrimidin-1-yl)acetamide dichloro­methane 0.62-solvate

Wang, N.; Guo, H.-M.; Hou, G.-G.; Hu, X.-Y.; Meng, Q.-G.

doi:10.1107/S1600536811034295

Volume 67
Part 9
Page o2464
September 2011

Received 30 July 2011
Accepted 21 August 2011
Online 27 August 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
Disorder in solvent or counterion
R = 0.092
wR = 0.209
Data-to-parameter ratio = 11.7
Details

N-Cyclopropyl-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-(1H-1,2,4-triazol-1-yl)propyl]-2-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetamide dichloromethane 0.62-solvate

Nan Wang,^a Huan-Mei Guo,^b Gui-Ge Hou,^c Xin-Yue Hu ^a and Qing-Guo Meng ^a ^*

^aSchool of Pharmacy, Yantai University, Yantai 264005, People's Republic of China,^bMicroscale Science Institute, Weifang University, Weifang 261041, People's Republic of China, and ^cSchool of Pharmacy, Binzhou Medical College, Yantai 264003, People's Republic of China
Correspondence e-mail: mqg@ytu.edu.cn

In the title compound, C₂₁H₂₂F₂N₆O₄·0.62CH₂Cl₂, the difluoro-substituted benzene ring forms dihedral angles of 54.6 (3)° with the mean plane of the thymine ring and 50.9 (2)° with the triazole ring. The dihedral angle between the thymine and triazole rings is 7.4 (3)°. In the crystal, intermolecular N-HN and O-HO hydrogen bonds link the main molecules into chains along [10 $[\overline{1}]$ ]. The CH₂Cl₂ solvent molecule was refined as partial occupancy over two sets of sites with refined occupancies of 0.308 (9) and 0.310 (8).

Related literature

For the applications of azole and triazole compounds as antifungal agents, see: Singh (2001); Richardson (2005); Hobson (2003); Slavin et al. (2002); Wingard & Leather (2004); Fridkin & Jarvis (1996); Gallis et al. (1990); Sheehan et al. (1999); Denning (2002); Aoyama et al. (1984); Lamb et al. (1999).

Experimental

Crystal data

C₂₁H₂₂F₂N₆O₄·0.62CH₂Cl₂
M_r = 512.93
Triclinic, $[P \overline 1]$
a = 8.474 (2) Å
b = 12.464 (3) Å
c = 13.410 (4) Å
= 62.942 (4)°
= 73.187 (4)°
= 83.746 (4)°
V = 1207.1 (6) Å³
Z = 2
Mo K radiation
= 0.24 mm^-1
T = 298 K
0.30 × 0.16 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer
6058 measured reflections
4162 independent reflections
3053 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.092
wR(F²) = 0.209
S = 1.16
4162 reflections
356 parameters
42 restraints
H-atom parameters constrained
_max = 0.50 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N6-H6N2ⁱ	0.80	2.11	2.893 (5)	167
O1-H1AO2ⁱⁱ	0.82	2.13	2.903 (4)	158
Symmetry codes: (i) x+1, y, z-1; (ii) -x+2, -y+1, -z+2.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: LH5302 ).

Acknowledgements

The authors thank Mr Lian-dong Liu (College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan, China) for his invaluable support in the X-ray data collection. The authors also thank the National Natural Science Foundation of China for a research grant (No. 81072534).

References

Aoyama, Y., Yoshida, Y. & Sato, R. (1984). J. Biol. Chem. 259, 1661-1666.
Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.
Denning, D. W. (2002). J. Antimicrob. Chemother. 49, 889-891.
Fridkin, S. K. & Jarvis, W. R. (1996). Clin. Microbiol. Rev. 9, 499-511.
Gallis, H. A., Drew, R. H. & Pickard, W. W. (1990). Rev. Infect. Dis. 12, 308-329.
Hobson, R. P. (2003). J. Hosp. Infect. 55, 159-168.
Lamb, D. C., Kelly, D. E., Venkateswarlu, K., Manning, N. J., Bligh, H. F., Schunck, W. H. & Kelly, S. L. (1999). Biochemistry. 38, 8733-8738.
Richardson, M. D. (2005). J. Antimicrob. Chemother. 56, i5-i11.
Sheehan, D. J., Hitchcock, C. A. & Sibley, C. M. (1999). Clin. Microbiol. Rev. 12, 40-79.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, N. (2001). Clin. Infect. Dis. 33, 1692-1696.
Slavin, M. A. et al. (2002). J. Antimicrob. Chemother. 49, 3-6.
Wingard, J. R. & Leather, H. (2004). Biol. Blood Marrow Transplant. 10, 73-90.

organic compounds