N-[(2-Chloro-3-quinol­yl)meth­yl]-4-fluoro­aniline

Jasinski, J.P.; Pek, A.E.; Chidan Kumar, C.S.; Yathirajan, H.S.; Kumar, S.

doi:10.1107/S1600536810036056

Volume 66
Part 10
Pages o2548-o2549
October 2010

Received 14 August 2010
Accepted 7 September 2010
Online 11 September 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.034
wR = 0.094
Data-to-parameter ratio = 21.7
Details

N-[(2-Chloro-3-quinolyl)methyl]-4-fluoroaniline

Jerry P. Jasinski,^a ^* Albert E. Pek,^a C. S. Chidan Kumar,^b H. S. Yathirajan ^b and Suresh Kumar ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Hamdard University, Jamia Hamdard, New Delhi 110 062, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C₁₆H₁₂ClFN₂, the dihedral angle between the quinoline ring system and the flourophenyl ring is 86.70 (4)°. In the crystal, molecules are linked into chains along the a axis by N-HN hydrogen bonds. In addition, C-H [pi] interactions involving the two benzene rings are observed.

Related literature

For general background, properties and the biological activity of quinolines, see: Campbell et al. (1988); Dutta et al. (2002); Markees et al. (1970); Meth-Cohn et al. (1981); Michael et al. (1997); Morimoto et al. (1991); Padwa et al. (1999); Rajendran & Karavembu (2002); Robert & Meunier et al. (1998). For the synthesis of quinolines, see: Kouznetsov et al. (2005). For related structures, see: Butcher et al. 2007); Lynch et al. (2001); Subashini et al. (2009); Yathirajan et al. (2007); Wu et al. (2009); Khan et al. (2010). For bond-length data, see: Allen et al. (1987) .

Experimental

Crystal data

C₁₆H₁₂ClFN₂
M_r = 286.73
Triclinic, $[P \overline 1]$
a = 7.3661 (8) Å
b = 8.8967 (9) Å
c = 11.5129 (12) Å
= 68.704 (1)°
= 74.468 (1)°
= 75.445 (1)°
V = 667.25 (12) Å³
Z = 2
Mo K radiation
= 0.29 mm^-1
T = 100 K
0.55 × 0.50 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.858, T_max = 0.932
8162 measured reflections
3930 independent reflections
3633 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.094
S = 1.03
3930 reflections
181 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C11-C16 rings, respectively.

D-HA	D-H	HA	DA	D-HA
N2-H18N1ⁱ	0.86	2.30	3.1353 (12)	165
C4-H4Cg2ⁱⁱ	0.93	2.91	3.7494 (13)	151
C10-H10ACg1ⁱⁱⁱ	0.97	2.62	3.5365 (12)	157
C10-H10BCg2^iv	0.97	2.98	3.8083 (11)	145
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y, -z+1; (iv) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5158 ).

Acknowledgements

JPJ thanks Dr Matthias Zeller and the YSU Department of Chemistry for their assistance with the data collection. The diffractometer was funded by NSF grant 0087210, by the Ohio Board of Regents grant CAP-491, and by YSU. CSC thanks the University of Mysore for research facilities and HSY thanks the University of Mysore for sabbatical leave.

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.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA
Butcher, R. J., Jasinski, J. P., Mayekar, A. N., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3603.
Campbell, S. F., Hardstone, J. D. & Palmer, M. J. (1988). J. Med. Chem. 31, 1031-1035.
Dutta, N. J., Khunt, R. C. & Parikh, A. R. (2002). Indian J. Chem. Sect. B, 41, 433-435.
Khan, F. N., Mohana Roopan, S., Hathwar, V. R. & Ng, S. W. (2010). Acta Cryst. E66, o201.
Kouznetsov, V. V., Vargas Mendez, L. Y. & Melendez Gomez, C. M. (2005). Curr. Org. Chem. 9, 141-161.
Lynch, D. E. & McClenaghan, I. (2001). Acta Cryst. E57, o54-o55.
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.
Meth-Cohn, O., Tarnowski, B., Hayear, R., Keyzad, A. & Rhouti, S. (1981). J. Chem. Soc. Perkin Trans. 1, pp. 2509-2517.
Michael, J. P. (1997). Nat. Prod. Rep. 14, 605-608.
Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.
Padwa, A., Brodney, M. A., Liu, B., Satake, K. & Wu, T. (1999). J. Org. Chem. 64, 3595-3607.
Rajendran, P. & Karavembu, R. (2002). Indian J. Chem. Sect. B, 41, 222-224.
Robert, A. & Meunier, B. (1998). Chem. Soc. Rev. 27, 273-279.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Subashini, R., Khan, F. N., Kumar, R., Hathwar, V. R. & Ng, S. W. (2009). Acta Cryst. E65, o2721.
Wu, T.-Q., Wang, J.-H., Shen, F. & Hu, A.-X. (2009). Acta Cryst. E65, o1463.
Yathirajan, H. S., Sreevidya, T. V., Prathap, M., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o763-o765.

organic compounds