[1-(3-Nitro­phen­yl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-3-ylidine]malonaldehyde

NizamMohideen, M.; SubbiahPandi, A.; Selvam, N.P.; Perumal, P.T.; Damodiran, M.

doi:10.1107/S1600536809006023

Volume 65
Part 3
Page o582
March 2009

Received 17 February 2009
Accepted 19 February 2009
Online 25 February 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.102
Data-to-parameter ratio = 11.9
Details

[1-(3-Nitrophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-3-ylidine]malonaldehyde

M. NizamMohideen,^a A. SubbiahPandi,^b ^* N. Panneer Selvam,^c P. T. Perumal ^c and M. Damodiran ^c

^aDepartment of Physics, The New College (Autonomous), Chennai 600 014, India,^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^cOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India
Correspondence e-mail: a_spandian@yahoo.com

The oxazine ring in the title compound, C₂₁H₁₄N₂O₅, adopts a flattened boat conformation. The nitrophenyl ring and the naphthalene ring system enclose a dihedral angle of 89.2 (1)°. An intramolecular hydrogen bond is formed between the NH group and one of the adjacent carbonyl O atoms. In addition, the NH group forms an intermolecular hydrogen bond to a symmetry equivalent of this carbonyl O atom, connecting the molecules into centrosymmetric dimers. The structure also contains C-HO intermolecular interactions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring puckering parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental

Crystal data

C₂₁H₁₄N₂O₅
M_r = 374.34
Monoclinic, P 2₁ /n
a = 7.9191 (4) Å
b = 23.3876 (11) Å
c = 9.6199 (5) Å
= 104.632 (2)°
V = 1723.91 (15) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 293 K
0.33 × 0.27 × 0.25 mm

Data collection

'Bruker Kappa APEXII CCD diffractometer'
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.897, T_max = 0.974
16263 measured reflections
3023 independent reflections
2334 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.102
S = 1.00
3023 reflections
253 parameters
H-atom parameters constrained
_max = 0.12 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O3ⁱ	0.93	2.54	3.395 (2)	153
C18-H18O4ⁱⁱ	0.93	2.44	3.259 (2)	148
N1-H1O4ⁱⁱ	0.86	2.36	3.078 (2)	141
N1-H1O4	0.86	2.02	2.670 (2)	132
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009)'.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2875 ).

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help in collecting the X-ray intensity data. MNM and ASP thank Dr J. Jothi Kumar, Principal of Presidency College, Chennai, India, for providing the computer and internet facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds