(E)-1-[(2-Amino-5-nitro­phen­yl)iminio­meth­yl]naphthalen-2-olate

Farag, A.M.; Teoh, S.G.; Osman, H.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536810014923

Volume 66
Part 5
Pages o1227-o1228
May 2010

Received 11 April 2010
Accepted 23 April 2010
Online 30 April 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.057
wR = 0.151
Data-to-parameter ratio = 17.7
Details

(E)-1-[(2-Amino-5-nitrophenyl)iminiomethyl]naphthalen-2-olate

Abeer Mohamed Farag,^a Siang Guan Teoh,^a Hasnah Osman,^a Suchada Chantrapromma ^b ⁺ and Hoong-Kun Fun ^c ^*⁺⁺

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The title Schiff base compound, C₁₇H₁₃N₃O₃, crystallizes in a zwitterionic form and exists in a trans configuration about the C=N bond. The molecule is slightly twisted, the dihedral angle between the benzene ring and naphthalene ring system being 10.80 (9)°. The nitro group is twisted relative to the plane of the benzene ring [dihedral angle = 8.88 (12)°]. Bifurcated intramolecular N-HN and N-HO hydrogen bonds formed between iminium groups and amine N atoms and naphthalen-2-olate O atoms generate S(5) and S(6) ring motifs, respectively. In the crystal, neighbouring zwitterions are linked through weak C-HO interactions, giving rise to screw chains along [010]. Molecules in these chains are linked to those of an adjacent chains through N-HO hydrogen bonds and weak C-HO interactions, forming sheets parallel to the ac plane. OC [2.895 (3) Å] short contacts and [pi] - [pi] interactions [centroid-centroid distance = 3.8249 (19) Å] are also observed.

Related literature

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to Schiff bases and their applications, see: Eltayeb et al. (2007; 2008); Dao et al. (2000); Kagkelari et al. (2009); Karthikeyan et al. (2006); Sondhi et al. (2006); Sriram et al. (2006). For related structures, see: Eltayeb et al. (2009; 2010). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental

Crystal data

C₁₇H₁₃N₃O₃
M_r = 307.30
Monoclinic, P 2₁ /c
a = 10.369 (4) Å
b = 4.6442 (18) Å
c = 28.539 (9) Å
= 103.548 (12)°
V = 1336.1 (8) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 100 K
0.48 × 0.10 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.950, T_max = 0.996
14018 measured reflections
3887 independent reflections
2341 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.151
S = 1.02
3887 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O1	1.01 (3)	1.61 (3)	2.505 (2)	146 (3)
N1-H1N1N2	1.01 (3)	2.39 (3)	2.737 (3)	100 (2)
N2-H1N2O1ⁱ	0.89 (3)	2.47 (3)	3.219 (3)	142.0 (19)
N2-H2N2O1ⁱⁱ	0.95 (3)	1.98 (3)	2.879 (3)	158.6 (19)
C6-H6AO3ⁱⁱⁱ	0.93	2.57	3.489 (3)	168
C15-H15AO2^iv	0.93	2.51	3.161 (3)	127
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+2, -y-1, -z+2; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+2, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: SJ2769 ).

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the RU research grants (1001/PKIMIA/815002 and 1001/PKIMIA/811120). AMF thanks the Libyan Government for providing a scholarship and Dr Naser Eltaher Eltayeb for his useful suggestions. The authors also thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805-813.
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o934-o935.
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, m570-m571.
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, m1672-m1673.
Eltayeb, N. E., Teoh, S. G., Yeap, C. S., Fun, H.-K. & Adnan, R. (2009). Acta Cryst. E65, o2065-o2066.
Kagkelari, A., Papaefstahiou, G. S., Raptopoulou, C. P. & Zafiropoulos, T. F. (2009). Polyhedron, 28, 3279-3283.
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sondhi, S. M., Singh, N., Kumar, A., Lozach, O. & Meijer, L. (2006). Bioorg. Med. Chem.. 14, 3758-3765.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.

organic compounds