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Journal List > Acta Crystallogr Sect E Struct Rep Online > v.64(Pt 9); Sep 1, 2008

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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
Copyright © Mansor et al. 2008
N-(2-Hydroxy­phen­yl)-4-nitro­phthalimide
Shahirah Mansor,a Norzalida Zakaria,a Azhar Ariffin,a and Seik Weng Nga*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received August 11, 2008; Accepted August 11, 2008.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Abstract
Mol­ecules of the title compound, C14H8N2O5, are linked by a hydr­oxy–amide O—H[cdots, three dots, centered]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]).
Click on image to enlarge
An external file that holds a picture, illustration, etc. Object name is e-64-o1770-scheme1.jpg Object name is e-64-o1770-scheme1.jpg
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
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025920/lh2681sup1.cif
Click here to view.(17K, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025920/lh2681Isup2.hkl
Click here to view.(80K, 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.
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 (more ...)
Crystal data
C14H8N2O5F000 = 584
Mr = 284.22Dx = 1.553 Mg m−3
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 mm−1
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 Å−3
199 parametersΔρmin = −0.28 e Å−3
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.
 
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.
  • 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.
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