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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1058.
Published online 2008 May 10. doi:  10.1107/S1600536808013548
PMCID: PMC2961600

N-(2-Methoxy­ethyl)phthalimide

Abstract

The title mol­ecule, C11H11NO3, lies on a crystallographic mirror plane which bis­ects the plane of the phthalimide unit and contains the C and O atoms of the 2-methoxy­ethyl group.

Related literature

For medicinal properties of the title compound, see: Chapman et al. (1989 [triangle]); Hall et al. (1994 [triangle]). For a kinetic study of the reaction that yields the title compound, see: Khan (1994 [triangle]).

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Object name is e-64-o1058-scheme1.jpg

Experimental

Crystal data

  • C11H11NO3
  • M r = 205.21
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1058-efi1.jpg
  • a = 7.0514 (2) Å
  • b = 9.3852 (2) Å
  • c = 14.6024 (4) Å
  • V = 966.37 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 (2) K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 7349 measured reflections
  • 1164 independent reflections
  • 986 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.206
  • S = 1.11
  • 1164 reflections
  • 77 parameters
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.50 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]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013548/lh2624sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013548/lh2624Isup2.hkl

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

Acknowledgments

We thank the SAGA grant (06–02-03–0147) for supporting this study, and the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

The title compound was previously reported in a kinetic study (Khan, 1994). We intend to carry out studies on the medicinal properties of the compound; some such properties have been reported (Chapman et al., 1989; Hall et al., 1994). The molecule of N-(2-methoxyethyl)phthalimide lies on a mirror plane that relates one half of the phthalamido portion of the molecule to the other; the 2-methoxyethyl substituent lies on the mirror plane itself (Fig. 1).

Experimental

Phthalic anhydride (2.59 g, 17.5 mmol) and 2-methoxyethylamine (1.50 ml, 17.5 mmol) were dissolved in acetic acid (25 ml). The mixture was heated at 393–413 K for 4 h; the reaction was monitored by TLC. Water was added to precipitate the product, which was collected (80% yield.) Crystals were obtained upon recrystallization from water.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5 U(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C11H11NO3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius. Symmetry transformation (i): x, 1/2 – y, z.

Crystal data

C11H11NO3F000 = 432
Mr = 205.21Dx = 1.410 Mg m3
Orthorhombic, PnmaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2463 reflections
a = 7.0514 (2) Åθ = 2.6–28.3º
b = 9.3852 (2) ŵ = 0.10 mm1
c = 14.6024 (4) ÅT = 100 (2) K
V = 966.37 (4) Å3Prism, colorless
Z = 40.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.6º
ω scansh = −8→9
Absorption correction: Nonek = −12→12
7349 measured reflectionsl = −12→18
1164 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)] = 0.059H-atom parameters constrained
wR(F2) = 0.206  w = 1/[σ2(Fo2) + (0.1433P)2 + 0.309P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
1164 reflectionsΔρmax = 0.50 e Å3
77 parametersΔρmin = −0.50 e Å3
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/UeqOcc. (<1)
O10.2012 (2)0.00647 (14)0.60172 (9)0.0229 (5)
O20.3277 (3)0.25000.33669 (12)0.0161 (5)
N10.2007 (4)0.25000.57847 (14)0.0167 (6)
C10.2372 (3)0.17575 (18)0.89087 (12)0.0176 (5)
H10.24340.12600.94750.021*
C20.2281 (3)0.09866 (19)0.80904 (12)0.0168 (5)
H20.2280−0.00260.80880.020*
C30.2194 (3)0.17598 (18)0.72848 (11)0.0144 (5)
C40.2072 (3)0.12658 (18)0.63197 (13)0.0171 (5)
C50.1763 (4)0.25000.47961 (16)0.0176 (6)
H5A0.10340.33540.46100.021*0.50
H5B0.10340.16460.46100.021*0.50
C60.3665 (4)0.25000.43155 (16)0.0175 (6)
H6A0.44040.33570.44860.021*0.50
H6B0.44040.16430.44860.021*0.50
C70.4974 (4)0.25000.28287 (17)0.0210 (7)
H7A0.46420.25000.21770.031*
H7B0.57210.16470.29700.031*0.50
H7C0.57210.33530.29700.031*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0377 (10)0.0142 (8)0.0166 (8)0.0009 (6)−0.0011 (6)−0.0037 (5)
O20.0210 (11)0.0178 (9)0.0093 (9)0.0000.0003 (7)0.000
N10.0282 (14)0.0143 (11)0.0075 (10)0.0000.0000 (8)0.000
C10.0240 (10)0.0185 (10)0.0102 (9)0.0008 (7)0.0016 (6)0.0018 (6)
C20.0237 (11)0.0134 (8)0.0133 (9)−0.0006 (7)0.0001 (7)0.0017 (6)
C30.0189 (10)0.0142 (9)0.0101 (9)0.0001 (7)0.0003 (6)−0.0012 (6)
C40.0258 (11)0.0133 (9)0.0121 (9)0.0011 (7)0.0006 (7)0.0004 (6)
C50.0220 (14)0.0216 (12)0.0091 (12)0.000−0.0024 (9)0.000
C60.0239 (15)0.0197 (11)0.0088 (12)0.000−0.0011 (9)0.000
C70.0284 (17)0.0196 (12)0.0149 (12)0.0000.0043 (11)0.000

Geometric parameters (Å, °)

O1—C41.211 (2)C3—C3i1.389 (3)
O2—C61.412 (3)C3—C41.486 (2)
O2—C71.432 (3)C5—C61.514 (4)
N1—C41.398 (2)C5—H5A0.9900
N1—C4i1.398 (2)C5—H5B0.9900
N1—C51.454 (3)C6—H6A0.9900
C1—C1i1.394 (3)C6—H6B0.9900
C1—C21.398 (2)C7—H7A0.9800
C1—H10.9500C7—H7B0.9800
C2—C31.384 (2)C7—H7C0.9800
C2—H20.9500
C6—O2—C7112.1 (2)N1—C5—H5A109.5
C4—N1—C4i111.9 (2)C6—C5—H5A109.5
C4—N1—C5123.97 (11)N1—C5—H5B109.5
C4i—N1—C5123.97 (11)C6—C5—H5B109.5
C1i—C1—C2121.16 (10)H5A—C5—H5B108.1
C1i—C1—H1119.4O2—C6—C5106.5 (2)
C2—C1—H1119.4O2—C6—H6A110.4
C3—C2—C1117.21 (17)C5—C6—H6A110.4
C3—C2—H2121.4O2—C6—H6B110.4
C1—C2—H2121.4C5—C6—H6B110.4
C2—C3—C3i121.63 (11)H6A—C6—H6B108.6
C2—C3—C4130.19 (16)O2—C7—H7A109.5
C3i—C3—C4108.18 (9)O2—C7—H7B109.5
O1—C4—N1124.48 (17)H7A—C7—H7B109.5
O1—C4—C3129.64 (16)O2—C7—H7C109.5
N1—C4—C3105.87 (15)H7A—C7—H7C109.5
N1—C5—C6110.8 (2)H7B—C7—H7C109.5
C1i—C1—C2—C30.1 (2)C3i—C3—C4—O1−179.02 (19)
C1—C2—C3—C3i−0.1 (2)C2—C3—C4—N1179.5 (2)
C1—C2—C3—C4−179.47 (19)C3i—C3—C4—N10.07 (17)
C4i—N1—C4—O1179.03 (13)C4—N1—C5—C6−92.3 (2)
C5—N1—C4—O13.2 (4)C4i—N1—C5—C692.3 (2)
C4i—N1—C4—C3−0.1 (3)C7—O2—C6—C5180.0
C5—N1—C4—C3−176.0 (2)N1—C5—C6—O2180.0
C2—C3—C4—O10.5 (4)

Symmetry codes: (i) x, −y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2624).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chapman, J. M., Sowell, J. W., Abdalla, G., Hall, I. H. & Wong, O. T. (1989). J. Pharm. Sci.78, 903–909. [PubMed]
  • Hall, I. H., Chapman, J. M. & Wong, O. T. (1994). Anti-Cancer Drugs, 5, 75–82. [PubMed]
  • Khan, M. N. (1994). Indian J. Chem. B33, 646–650.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [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