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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1770.
Published online 2008 August 16. doi:  10.1107/S1600536808025920
PMCID: PMC2960742

N-(2-Hydroxy­phen­yl)-4-nitro­phthalimide

Abstract

Mol­ecules of the title compound, C14H8N2O5, are linked by a hydr­oxy–amide O—H(...)O 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 [triangle]; 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1770-scheme1.jpg

Experimental

Crystal data

  • C14H8N2O5
  • M r = 284.22
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1770-efi1.jpg
  • a = 7.1114 (2) Å
  • b = 11.7646 (3) Å
  • c = 14.5304 (4) Å
  • V = 1215.65 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 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 > 2σ(I)
  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.142
  • S = 1.04
  • 1618 reflections
  • 199 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.28 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025920/lh2681sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025920/lh2681Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound (Fig. 1) was synthesized for studies on intramolecular general base (IGB) and intramolecular general acid (IGA) catalysis in the hydrolysis of N-substitutedphthalimide (Sim et al., 2006; 2007).

Experimental

4-Nitrophthalic anhydride (5.0 g, 26 mmol) and o-hydroxyaniline (3.4 g, 31 mmol) were heated in glacial acetic acid (15 mol) for 4 h at 393–401 K. The reaction was shown to be complete by thin layer chromatography. The mixture was poured into water. The yellow solid was collected in 90% yield; purification was effected by recrystallization from chloroform.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The hydroxy group is disordered over two positions on the phenylene ring; the disorder refined to a 0.571 (1):429 (1) ratio.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of O–H···O hydrogen-bonded structure of C14H8N2O3 at the 70% probability level. Dashed lines denote the intermolecular hydrogen bonds. Hydrogen atoms are drawn as spheres of arbitrary ...

Crystal data

C14H8N2O5F000 = 584
Mr = 284.22Dx = 1.553 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2147 reflections
a = 7.1114 (2) Åθ = 2.8–23.8º
b = 11.7646 (3) ŵ = 0.12 mm1
c = 14.5304 (4) ÅT = 100 (2) K
V = 1215.65 (6) Å3Prism, yellow
Z = 40.32 × 0.06 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer1356 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.087
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.2º
ω scansh = −9→9
Absorption correction: Nonek = −15→15
13791 measured reflectionsl = −18→18
1618 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.142  w = 1/[σ2(Fo2) + (0.0803P)2 + 0.3691P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
1618 reflectionsΔρmax = 0.36 e Å3
199 parametersΔρmin = −0.28 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.3544 (4)0.2939 (3)0.8037 (3)0.0308 (10)0.571 (3)
H10.24900.30650.77970.046*0.571 (3)
O1'0.8498 (5)0.4876 (3)0.9237 (4)0.0287 (13)0.429 (3)
H1'0.91400.42840.91620.043*0.429 (3)
O20.4761 (4)0.1944 (2)0.97117 (17)0.0362 (6)
O30.9695 (3)0.3018 (2)0.78879 (18)0.0347 (6)
O41.3585 (4)−0.0916 (2)0.8641 (2)0.0455 (8)
O51.1873 (5)−0.2264 (2)0.9238 (2)0.0533 (9)
N10.7000 (4)0.2751 (2)0.87514 (18)0.0217 (6)
N21.2106 (5)−0.1285 (3)0.8959 (2)0.0383 (8)
C10.4328 (5)0.3850 (3)0.8206 (2)0.0307 (8)
H1A0.36760.31630.80800.037*0.429 (3)
C20.3486 (7)0.4888 (4)0.8022 (3)0.0493 (12)
H20.22300.49150.78000.059*
C30.4465 (8)0.5871 (4)0.8161 (3)0.0537 (13)
H30.39040.65780.80060.064*
C40.6260 (9)0.5852 (3)0.8525 (3)0.0543 (14)
H40.69310.65420.86160.065*
C50.7071 (6)0.4825 (3)0.8755 (3)0.0390 (9)
H5A0.82760.48060.90370.047*0.571 (3)
C60.6120 (5)0.3820 (3)0.8574 (2)0.0271 (7)
C70.6224 (5)0.1884 (3)0.9290 (2)0.0237 (7)
C80.7584 (5)0.0922 (3)0.9252 (2)0.0236 (7)
C90.7433 (5)−0.0146 (3)0.9637 (2)0.0287 (7)
H90.6348−0.03710.99720.034*
C100.8946 (5)−0.0877 (3)0.9510 (2)0.0305 (8)
H100.8915−0.16250.97560.037*
C111.0478 (5)−0.0508 (3)0.9029 (2)0.0270 (7)
C121.0651 (5)0.0568 (3)0.8618 (2)0.0276 (7)
H121.17330.07930.82810.033*
C130.9122 (4)0.1269 (3)0.8746 (2)0.0244 (7)
C140.8758 (4)0.2439 (3)0.8398 (2)0.0226 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.021 (2)0.032 (2)0.039 (2)0.0014 (18)−0.0039 (18)0.000 (2)
O1'0.025 (3)0.023 (2)0.039 (3)−0.003 (2)−0.014 (2)0.000 (2)
O20.0371 (14)0.0391 (13)0.0322 (14)0.0103 (12)0.0161 (11)0.0066 (11)
O30.0246 (12)0.0454 (15)0.0341 (13)0.0017 (12)0.0003 (11)0.0114 (12)
O40.0307 (14)0.0623 (19)0.0435 (15)0.0172 (13)0.0023 (13)−0.0015 (14)
O50.070 (2)0.0364 (14)0.0534 (18)0.0275 (15)0.0170 (17)0.0133 (14)
N10.0209 (12)0.0235 (13)0.0206 (13)0.0047 (10)−0.0020 (11)0.0006 (11)
N20.0418 (17)0.0448 (18)0.0285 (16)0.0170 (15)0.0059 (14)−0.0016 (15)
C10.0310 (17)0.0420 (19)0.0191 (15)0.0149 (16)0.0059 (13)0.0048 (15)
C20.053 (3)0.058 (3)0.036 (2)0.035 (2)0.017 (2)0.025 (2)
C30.081 (3)0.048 (3)0.032 (2)0.042 (3)0.021 (2)0.0186 (19)
C40.109 (4)0.0286 (19)0.0250 (19)0.013 (2)0.011 (3)0.0013 (16)
C50.066 (3)0.0290 (17)0.0217 (18)0.0023 (18)−0.0074 (19)0.0015 (15)
C60.0371 (17)0.0255 (15)0.0186 (15)0.0124 (14)0.0028 (14)0.0026 (13)
C70.0313 (16)0.0246 (14)0.0152 (14)0.0044 (13)−0.0018 (13)−0.0005 (12)
C80.0268 (15)0.0257 (15)0.0184 (15)0.0057 (12)0.0005 (13)−0.0024 (13)
C90.0309 (16)0.0302 (16)0.0250 (17)0.0010 (14)0.0018 (14)−0.0009 (14)
C100.0351 (17)0.0284 (17)0.0280 (17)0.0038 (14)−0.0024 (15)−0.0038 (14)
C110.0324 (16)0.0288 (16)0.0198 (15)0.0129 (14)−0.0041 (13)−0.0051 (14)
C120.0255 (15)0.0382 (18)0.0191 (15)0.0056 (14)−0.0033 (13)−0.0003 (14)
C130.0229 (14)0.0288 (16)0.0214 (14)0.0054 (12)−0.0057 (13)−0.0038 (14)
C140.0206 (14)0.0279 (15)0.0194 (15)0.0014 (12)−0.0040 (12)0.0012 (13)

Geometric parameters (Å, °)

O1—C11.233 (5)C3—C41.382 (8)
O1—H10.8400C3—H30.9500
O1'—C51.234 (5)C4—C51.380 (6)
O1'—H1'0.8400C4—H40.9500
O2—C71.210 (4)C5—C61.388 (5)
O3—C141.207 (4)C5—H5A0.9500
O4—N21.228 (4)C7—C81.490 (4)
O5—N21.232 (4)C8—C91.380 (5)
N1—C141.401 (4)C8—C131.379 (4)
N1—C71.399 (4)C9—C101.389 (5)
N1—C61.428 (4)C9—H90.9500
N2—C111.478 (4)C10—C111.366 (5)
C1—C61.382 (5)C10—H100.9500
C1—C21.386 (5)C11—C121.405 (5)
C1—H1A0.9500C12—C131.377 (4)
C2—C31.365 (8)C12—H120.9500
C2—H20.9500C13—C141.490 (5)
C1—O1—H1109.5C1—C6—C5120.1 (3)
C5—O1'—H1'109.5C1—C6—N1119.8 (3)
C14—N1—C7111.5 (3)C5—C6—N1120.1 (3)
C14—N1—C6123.7 (3)O2—C7—N1125.5 (3)
C7—N1—C6124.8 (3)O2—C7—C8128.4 (3)
O4—N2—O5124.7 (3)N1—C7—C8106.1 (3)
O4—N2—C11118.6 (3)C9—C8—C13123.1 (3)
O5—N2—C11116.7 (3)C9—C8—C7128.8 (3)
O1—C1—C6118.1 (3)C13—C8—C7108.1 (3)
O1—C1—C2122.1 (4)C8—C9—C10116.8 (3)
C6—C1—C2119.7 (4)C8—C9—H9121.6
C6—C1—H1A120.1C10—C9—H9121.6
C2—C1—H1A120.1C11—C10—C9119.2 (3)
C3—C2—C1119.8 (4)C11—C10—H10120.4
C3—C2—H2120.1C9—C10—H10120.4
C1—C2—H2120.1C10—C11—C12125.0 (3)
C2—C3—C4121.0 (4)C10—C11—N2117.6 (3)
C2—C3—H3119.5C12—C11—N2117.3 (3)
C4—C3—H3119.5C13—C12—C11114.4 (3)
C5—C4—C3119.5 (5)C13—C12—H12122.8
C5—C4—H4120.2C11—C12—H12122.8
C3—C4—H4120.2C12—C13—C8121.4 (3)
O1'—C5—C4116.1 (4)C12—C13—C14130.2 (3)
O1'—C5—C6123.4 (3)C8—C13—C14108.4 (3)
C4—C5—C6119.7 (4)O3—C14—N1124.8 (3)
C4—C5—H5A120.1O3—C14—C13129.3 (3)
C6—C5—H5A120.1N1—C14—C13105.8 (3)
O1—C1—C2—C3−175.3 (4)C13—C8—C9—C101.3 (5)
C6—C1—C2—C33.3 (5)C7—C8—C9—C10−178.6 (3)
C1—C2—C3—C4−3.1 (6)C8—C9—C10—C110.5 (5)
C2—C3—C4—C5−0.3 (6)C9—C10—C11—C12−1.6 (5)
C3—C4—C5—O1'−166.2 (4)C9—C10—C11—N2176.2 (3)
C3—C4—C5—C63.5 (6)O4—N2—C11—C10−170.1 (3)
O1—C1—C6—C5178.5 (4)O5—N2—C11—C109.1 (5)
C2—C1—C6—C5−0.1 (5)O4—N2—C11—C127.9 (5)
O1—C1—C6—N1−0.4 (5)O5—N2—C11—C12−172.9 (3)
C2—C1—C6—N1−179.1 (3)C10—C11—C12—C130.9 (5)
O1'—C5—C6—C1165.7 (4)N2—C11—C12—C13−177.0 (3)
C4—C5—C6—C1−3.2 (5)C11—C12—C13—C81.0 (5)
O1'—C5—C6—N1−15.3 (6)C11—C12—C13—C14−177.8 (3)
C4—C5—C6—N1175.7 (3)C9—C8—C13—C12−2.1 (5)
C14—N1—C6—C1124.8 (3)C7—C8—C13—C12177.8 (3)
C7—N1—C6—C1−54.7 (4)C9—C8—C13—C14176.9 (3)
C14—N1—C6—C5−54.1 (4)C7—C8—C13—C14−3.2 (3)
C7—N1—C6—C5126.3 (4)C7—N1—C14—O3177.4 (3)
C14—N1—C7—O2176.5 (3)C6—N1—C14—O3−2.1 (5)
C6—N1—C7—O2−3.9 (5)C7—N1—C14—C130.0 (3)
C14—N1—C7—C8−1.8 (3)C6—N1—C14—C13−179.6 (3)
C6—N1—C7—C8177.8 (3)C12—C13—C14—O33.7 (6)
O2—C7—C8—C94.8 (6)C8—C13—C14—O3−175.3 (3)
N1—C7—C8—C9−177.0 (3)C12—C13—C14—N1−179.0 (3)
O2—C7—C8—C13−175.1 (3)C8—C13—C14—N12.1 (3)
N1—C7—C8—C133.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.841.992.747 (4)149
O1'—H1'···O2ii0.842.232.779 (4)123

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, −z+2.

Footnotes

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

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. [PubMed]
  • 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. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography