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Volume 69 
Part 9 
Page o1440  
September 2013  

Received 21 July 2013
Accepted 29 July 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.099
Data-to-parameter ratio = 12.4
Details
Open access

2,6-Difluoro-N-(prop-2-ynyl)benzamide

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bDepartment of Biochemistry, Faculty of Science, King Abdulaziz University, Jaddhah, Saudi Arabia
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the molecule of the title difluorobenzamide derivative, C10H7F2NO, the angle formed by the least-squares mean line through the prop-2-ynyl group [maximum deviation = 0.011 (3) Å] and the normal to the benzene ring is 59.03 (7)°. In the crystal, molecules are linked via N-H...O and C-H...F hydrogen bonds into layers parallel to the ac plane.

Related literature

For the biological activity of difluorobenzamide derivatives, see: Chang et al. (2002[Chang, Y. Y., Chung, Y. H., Lee, C. W., Lee, H. D., Lee, J. S., Park, W. J. & Yang, W. Y. (2002). Patent AU2002345403.]); Kees et al. (1989[Kees, K. L., Cheeseman, R. S., Prozialeck, D. H. & Steiner, K. E. (1989). J. Med. Chem., 32, 11-13.]); Ragavan et al. (2010[Ragavan, R. V., Vijayakumar, V. & Kumari, S. N. (2010). Eur. J. Med. Chem. 43, 1173-1180.]); Carmellino et al. (1994[Carmellino, M. L., Pagani, G., Pregnolato, M., Terreni, M. & Pastoni, F. (1994). Eur. J. Med. Chem. 29, 743-751.]); Rauko et al. (2001[Rauko, P., Novotny, L., Dovinova, I., Hunakova, L., Szekeres, T. & Jayaram, H. N. (2001). Eur. J. Pharm. Sci. 12, 387-394.]). For the crystal structure of a related compound, see: Fun et al. (2010[Fun, H.-K., Goh, J. H., Gowda, J., Khader, A. M. & Kalluraya, B. (2010). Acta Cryst. E66, o3192.]).

[Scheme 1]

Experimental

Crystal data
  • C10H7F2NO

  • Mr = 195.17

  • Monoclinic, P 21 /c

  • a = 5.0479 (8) Å

  • b = 19.738 (3) Å

  • c = 9.2428 (15) Å

  • [beta] = 91.432 (4)°

  • V = 920.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 273 K

  • 0.38 × 0.17 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • 5388 measured reflections

  • 1669 independent reflections

  • 1283 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.099

  • S = 1.03

  • 1669 reflections

  • 135 parameters

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

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.83 (2) 2.10 (2) 2.8387 (19) 147.4 (17)
C2-H2A...F2ii 0.93 2.49 3.394 (2) 164
Symmetry codes: (i) x-1, y, z; (ii) [x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5082 ).


References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Carmellino, M. L., Pagani, G., Pregnolato, M., Terreni, M. & Pastoni, F. (1994). Eur. J. Med. Chem. 29, 743-751.  [CrossRef] [ChemPort] [ISI]
Chang, Y. Y., Chung, Y. H., Lee, C. W., Lee, H. D., Lee, J. S., Park, W. J. & Yang, W. Y. (2002). Patent AU2002345403.
Fun, H.-K., Goh, J. H., Gowda, J., Khader, A. M. & Kalluraya, B. (2010). Acta Cryst. E66, o3192.  [CSD] [CrossRef] [details]
Kees, K. L., Cheeseman, R. S., Prozialeck, D. H. & Steiner, K. E. (1989). J. Med. Chem., 32, 11-13.  [CrossRef] [ChemPort] [PubMed] [ISI]
Ragavan, R. V., Vijayakumar, V. & Kumari, S. N. (2010). Eur. J. Med. Chem. 43, 1173-1180.  [ISI] [CrossRef]
Rauko, P., Novotny, L., Dovinova, I., Hunakova, L., Szekeres, T. & Jayaram, H. N. (2001). Eur. J. Pharm. Sci. 12, 387-394.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1440  [ doi:10.1107/S1600536813021120 ]

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