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Volume 66 
Part 2 
Pages o422-o423  
February 2010  

Received 23 December 2009
Accepted 15 January 2010
Online 23 January 2010

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.052
wR = 0.152
Data-to-parameter ratio = 23.3
Details
Open access

N,N'-Bis[(E)-2-fluorobenzylidene]-1-(2-fluorophenyl)methanediamine

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and dDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C21H15F3N2, the benzene ring bonded to the central C atom forms dihedral angles of 77.5 (7) and 89.0 (5)°, respectively, with the remaining two benzene rings. Weak intermolecular C-H...F hydrogen bonds link the molecules into chains propagated in [101]. The crystal packing exhibits weak [pi]-[pi] interactions as evidenced by relatively short distances between the centroids of the aromatic rings [3.820 (7) and 3.971 (5) Å]. A MOPAC PM3 optimization of the molecular geometry in vacuo supports a suggestion that intermolecular forces have a significnt influence on the molecular conformation in the crystal.

Related literature

For aromatic aldehyde reactions, see Williams & Bailar (1959[Williams, O. F. & Bailar, J. C. (1959). J. Am. Chem. Soc. 81, 4464-4469.]). For kinetics of hydrobenzamides, see Crampton et al. (1997[Crampton, M. R., Lord, S. D. & Millar, R. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 909-914.]). For conventional preparation of hydrobenzamides, see Kamal & Qureshi (1963[Kamal, K. A. & Qureshi, A. A. (1963). Tetrahedron, 19, 869-872.]). For related structures, see: Corey & Kuhnle (1997[Corey, E. T. & Kuhnle, F. M. (1997). Tetrahedron Lett. 38, 8631-8634.]); Karupaiyan et al. (1998[Karupaiyan, K., Srirajan, V., Deshmukh, A. R. A. S. & Bhawal, B. M. (1998). Tetrahedron, 54, 4375-4386.]); Saigo et al. (1986[Saigo, K., Kubota, N., Takabayashi, S. & Hasegawa, M. (1986). Bull. Chem. Soc. Jpn, 59, 931-932.]). For bond-length data, 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.]). For the synthesis of nitrogen-containing heterocyclic compounds, see Kupfer & Brinker (1996[Kupfer, R. & Brinker, U. H. (1996). J. Org. Chem. 61, 4185-4186.]). For MOPAC PM3 calculations, see Schmidt & Polik (2007[Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro. WebMO, LLC: Holland, MI, USA, available from http://www.webmo.net.]).

[Scheme 1]

Experimental

Crystal data
  • C21H15F3N2

  • Mr = 352.35

  • Triclinic, [P \overline 1]

  • a = 8.0215 (5) Å

  • b = 9.3740 (4) Å

  • c = 11.9744 (6) Å

  • [alpha] = 99.184 (4)°

  • [beta] = 93.179 (5)°

  • [gamma] = 108.165 (5)°

  • V = 839.23 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 200 K

  • 0.49 × 0.29 × 0.22 mm

Data collection
  • Oxford Diffraction Gemini diffractometer

  • 11550 measured reflections

  • 5484 independent reflections

  • 3292 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.152

  • S = 1.00

  • 5484 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.57 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5B-H5BA...F1Ai 0.95 2.53 3.3871 (16) 151
Symmetry code: (i) x+1, y, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO . Oxford Diffraction Ltd, Abingdon, 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: 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: CV2683 ).


Acknowledgements

QNMHA thanks the University of Mysore for use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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.
Corey, E. T. & Kuhnle, F. M. (1997). Tetrahedron Lett. 38, 8631-8634.  [CrossRef] [ChemPort] [ISI]
Crampton, M. R., Lord, S. D. & Millar, R. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 909-914.
Kamal, K. A. & Qureshi, A. A. (1963). Tetrahedron, 19, 869-872.  [CrossRef] [ChemPort] [ISI]
Karupaiyan, K., Srirajan, V., Deshmukh, A. R. A. S. & Bhawal, B. M. (1998). Tetrahedron, 54, 4375-4386.  [ISI] [CrossRef] [ChemPort]
Kupfer, R. & Brinker, U. H. (1996). J. Org. Chem. 61, 4185-4186.  [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2007). CrysAlis PRO . Oxford Diffraction Ltd, Abingdon, England.
Saigo, K., Kubota, N., Takabayashi, S. & Hasegawa, M. (1986). Bull. Chem. Soc. Jpn, 59, 931-932.  [CrossRef] [ChemPort] [ISI]
Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro. WebMO, LLC: Holland, MI, USA, available from http://www.webmo.net.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Williams, O. F. & Bailar, J. C. (1959). J. Am. Chem. Soc. 81, 4464-4469.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2010). E66, o422-o423   [ doi:10.1107/S1600536810001984 ]

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