N-(2-Hydroxy­phen­yl)-4-nitro­phthalimide

Mansor, S.; Zakaria, N.; Ariffin, A.; Ng, S.W.

doi:10.1107/S1600536808025920

Volume 64
Part 9
Page o1770
September 2008

Received 11 August 2008
Accepted 11 August 2008
Online 16 August 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.050
wR = 0.142
Data-to-parameter ratio = 8.1
Details

N-(2-Hydroxyphenyl)-4-nitrophthalimide

Shahirah Mansor,^a Norzalida Zakaria,^a Azhar Ariffin ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

Molecules of the title compound, C₁₄H₈N₂O₅, are linked by a hydroxy-amide O-HO hydrogen bond into a linear chain. The hydroxy group is disordered over two positions of the benzene ring in an approximate 0.57:0.43 ratio.

Related literature

For literature on the hydrolysis of N-substituted phthalimides, see: Sim et al. (2006; 2007).

Experimental

Crystal data

C₁₄H₈N₂O₅
M_r = 284.22
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.1114 (2) Å
b = 11.7646 (3) Å
c = 14.5304 (4) Å
V = 1215.65 (6) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 100 (2) K
0.32 × 0.06 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
13791 measured reflections
1618 independent reflections
1356 reflections with I > 2(I)
R_int = 0.087

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.142
S = 1.04
1618 reflections
199 parameters
2 restraints
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3ⁱ	0.84	1.99	2.747 (4)	149
O1'-H1'O2ⁱⁱ	0.84	2.23	2.779 (4)	123
Symmetry codes: (i) x-1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2681 ).

Acknowledgements

We thank MOSTI (grant No. 14-02-03-4014) and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sim, Y. L., Ariffin, A. & Khan, M. N. (2006). Int. J. Chem. Kinet. 38, 746-758.
Sim, Y. L., Ariffin, A. & Khan, M. N. (2007). J. Org. Chem. 72, 2392-2401.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds