organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-(2-Meth­oxy­ethyl)phthalimide

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

(Received 30 April 2008; accepted 7 May 2008; online 10 May 2008)

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[Chapman, J. M., Sowell, J. W., Abdalla, G., Hall, I. H. & Wong, O. T. (1989). J. Pharm. Sci. 78, 903-909.]); Hall et al. (1994[Hall, I. H., Chapman, J. M. & Wong, O. T. (1994). Anti-Cancer Drugs, 5, 75-82.]). For a kinetic study of the reaction that yields the title compound, see: Khan (1994[Khan, M. N. (1994). Indian J. Chem. B33, 646-650.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11NO3

  • Mr = 205.21

  • Orthorhombic, P n m a

  • 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)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top
[Figure 1] 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.
N-(2-Methoxyethyl)phthalimide top
Crystal data top
C11H11NO3F(000) = 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 = 2.6–28.3°
b = 9.3852 (2) ŵ = 0.10 mm1
c = 14.6024 (4) ÅT = 100 K
V = 966.37 (4) Å3Prism, colorless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer
986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
ω scansh = 89
7349 measured reflectionsk = 1212
1164 independent reflectionsl = 1218
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.1433P)2 + 0.309P]
where P = (Fo2 + 2Fc2)/3
1164 reflections(Δ/σ)max = 0.001
77 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.50 e Å3
Crystal data top
C11H11NO3V = 966.37 (4) Å3
Mr = 205.21Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 7.0514 (2) ŵ = 0.10 mm1
b = 9.3852 (2) ÅT = 100 K
c = 14.6024 (4) Å0.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer
986 reflections with I > 2σ(I)
7349 measured reflectionsRint = 0.039
1164 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 1.11Δρmax = 0.50 e Å3
1164 reflectionsΔρmin = 0.50 e Å3
77 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H20.22800.00260.80880.020*
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) top
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)0.0000.0024 (9)0.000
C60.0239 (15)0.0197 (11)0.0088 (12)0.0000.0011 (9)0.000
C70.0284 (17)0.0196 (12)0.0149 (12)0.0000.0043 (11)0.000
Geometric parameters (Å, º) top
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—O1179.02 (19)
C1—C2—C3—C3i0.1 (2)C2—C3—C4—N1179.5 (2)
C1—C2—C3—C4179.47 (19)C3i—C3—C4—N10.07 (17)
C4i—N1—C4—O1179.03 (13)C4—N1—C5—C692.3 (2)
C5—N1—C4—O13.2 (4)C4i—N1—C5—C692.3 (2)
C4i—N1—C4—C30.1 (3)C7—O2—C6—C5180.0
C5—N1—C4—C3176.0 (2)N1—C5—C6—O2180.0
C2—C3—C4—O10.5 (4)
Symmetry code: (i) x, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC11H11NO3
Mr205.21
Crystal system, space groupOrthorhombic, Pnma
Temperature (K)100
a, b, c (Å)7.0514 (2), 9.3852 (2), 14.6024 (4)
V3)966.37 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7349, 1164, 986
Rint0.039
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.206, 1.11
No. of reflections1164
No. of parameters77
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.50

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChapman, J. M., Sowell, J. W., Abdalla, G., Hall, I. H. & Wong, O. T. (1989). J. Pharm. Sci. 78, 903–909.  CrossRef CAS PubMed Web of Science Google Scholar
First citationHall, I. H., Chapman, J. M. & Wong, O. T. (1994). Anti-Cancer Drugs, 5, 75–82.  CrossRef CAS PubMed Web of Science Google Scholar
First citationKhan, M. N. (1994). Indian J. Chem. B33, 646–650.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
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