[Journal logo]

Volume 69 
Part 6 
Pages o996-o997  
June 2013  

Received 19 May 2013
Accepted 21 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.042
wR = 0.111
Data-to-parameter ratio = 13.7
Details
Open access

2-(4-Chlorophenyl)-N-(3,4-difluorophenyl)acetamide

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and dDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C14H10ClF2NO, the dihedral angle between the mean planes of the 4-chlorophenyl and 3,4-difluorophenyl rings is 65.2 (1)°. These two planes are twisted by 83.5 (5) and 38.9 (9)°, respectively, from that of the acetamide group. In the crystal, N-H...O hydrogen bonds form infinite chains along [100]. Weak C-H...O and C-H...F interactions are also observed and stack molecules along the b axis.

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006[Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.]); Mijin et al. (2008[Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.]). For the coordination abilities of amides, see: Wu et al. (2008[Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.], 2010[Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.]). For related structures, see: Praveen et al. (2011a[Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o1826.],b[Praveen, A. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Narayana, B. (2011b). Acta Cryst. E67, o2602-o2603.],c[Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011c). Acta Cryst. E67, o2604.], 2012[Praveen, A. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o226-o227.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10ClF2NO

  • Mr = 281.68

  • Orthorhombic, P 21 21 21

  • a = 4.8935 (5) Å

  • b = 5.8995 (6) Å

  • c = 42.572 (4) Å

  • V = 1229.0 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.92 mm-1

  • T = 173 K

  • 0.36 × 0.18 × 0.08 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.608, Tmax = 1.000

  • 7056 measured reflections

  • 2358 independent reflections

  • 2293 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.111

  • S = 1.14

  • 2358 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

  • Absolute structure: Flack x determined using 852 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.]).

  • Flack parameter: -0.003 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.88 1.97 2.854 (4) 177
C5-H5...O1ii 0.95 2.63 3.307 (4) 129
C14-H14...F1iii 0.95 2.69 3.615 (5) 164
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x-1, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5323 ).


Acknowledgements

ASP thanks the University of Mysore for research facilities. BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.  [ISI] [CrossRef] [ChemPort]
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.  [ISI] [CrossRef] [ChemPort]
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [details]
Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o1826.  [CSD] [CrossRef] [details]
Praveen, A. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Narayana, B. (2011b). Acta Cryst. E67, o2602-o2603.  [CSD] [CrossRef] [ChemPort] [details]
Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011c). Acta Cryst. E67, o2604.  [CSD] [CrossRef] [details]
Praveen, A. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o226-o227.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.  [ISI] [CrossRef] [ChemPort]
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o996-o997   [ doi:10.1107/S1600536813014165 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.