N-(2,3,4-Trifluoro­phen­yl)morpholine-4-carboxamide

Jie, L.; Shuchen, P.; Li, H.; Yong, W.

doi:10.1107/S1600536811051300

Volume 68
Part 1
Page o13
January 2012

Received 19 November 2011
Accepted 29 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.103
Data-to-parameter ratio = 12.0
Details

N-(2,3,4-Trifluorophenyl)morpholine-4-carboxamide

Li Jie,^a Pei Shuchen,^a Hai Li ^a and Wu Yong ^a ^*

^aKey Laboratory of Drug Targeting of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China
Correspondence e-mail: wyong@scu.edu.cn

In title molecule, C₁₁H₁₁F₃N₂O₂, the central -N-C(=O)-N- unit is essentially planar [maximum deviation = 0.013 (2) Å] and forms a dihedral angle of 57.33 (9)° with the benzene ring. The morpholine ring is in a chair conformation. In the crystal, molecules are linked into chains along [001] by N-HO hydrogen bonds.

Related literature

For background to urea derivatives as antibacterial and antifungal agents, see: Zheng et al. (2010).

Experimental

Crystal data

C₁₁H₁₁F₃N₂O₂
M_r = 260.22
Monoclinic, P 2₁ /c
a = 7.8515 (4) Å
b = 17.8264 (6) Å
c = 8.6872 (4) Å
= 109.790 (5)°
V = 1144.09 (8) Å³
Z = 4
Mo K radiation
= 0.14 mm^-1
T = 293 K
0.40 × 0.35 × 0.30 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.994, T_max = 1.000
4250 measured reflections
2009 independent reflections
1587 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.103
S = 1.07
2009 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.15 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.843 (18)	2.120 (19)	2.9306 (19)	161.2 (17)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009); software used to prepare material for publication: OLEX2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5385 ).

Acknowledgements

The authors thank the NSFC(81102324) for financial support and Professor Zhihua Mao (Sichuan University) for the X-ray measurements

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zheng, Q. Z., Cheng, H. K., Zhang, X. M., Liu, K., Jiao, Q. C. & Zhu, H. L. (2010). Eur. J. Med. Chem. 45, 3207-3212.

organic compounds