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

Jasinski, J.P.; Butcher, R.J.; Hakim Al-Arique, Q.N.M.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536810001984

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 (C-C) = 0.002 Å
R = 0.052
wR = 0.152
Data-to-parameter ratio = 23.3
Details

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

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b Q. N. M. Hakim Al-Arique,^c H. S. Yathirajan ^c and B. Narayana ^d

^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-HF 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). For kinetics of hydrobenzamides, see Crampton et al. (1997). For conventional preparation of hydrobenzamides, see Kamal & Qureshi (1963). For related structures, see: Corey & Kuhnle (1997); Karupaiyan et al. (1998); Saigo et al. (1986). For bond-length data, see: Allen et al. (1987). For the synthesis of nitrogen-containing heterocyclic compounds, see Kupfer & Brinker (1996). For MOPAC PM3 calculations, see Schmidt & Polik (2007).

Experimental

Crystal data

C₂₁H₁₅F₃N₂
M_r = 352.35
Triclinic, $[P \overline 1]$
a = 8.0215 (5) Å
b = 9.3740 (4) Å
c = 11.9744 (6) Å
= 99.184 (4)°
= 93.179 (5)°
= 108.165 (5)°
V = 839.23 (8) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.152
S = 1.00
5484 reflections
235 parameters
H-atom parameters constrained
_max = 0.57 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5B-H5BAF1Aⁱ	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); 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: 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.
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.
Karupaiyan, K., Srirajan, V., Deshmukh, A. R. A. S. & Bhawal, B. M. (1998). Tetrahedron, 54, 4375-4386.
Kupfer, R. & Brinker, U. H. (1996). J. Org. Chem. 61, 4185-4186.
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.
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.
Williams, O. F. & Bailar, J. C. (1959). J. Am. Chem. Soc. 81, 4464-4469.

organic compounds