Acta Cryst. (2008). E64, o1058 [ doi:10.1107/S1600536808013548 ]
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.
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.
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).
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).
![[Figure 1]](./lh2624fig1thm.gif)
| 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. |
| C11H11NO3 | F000 = 432 |
| Mr = 205.21 | Dx = 1.410 Mg m−3 |
| Orthorhombic, Pnma | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ac 2n | Cell parameters from 2463 reflections |
| a = 7.0514 (2) Å | θ = 2.6–28.3º |
| b = 9.3852 (2) Å | µ = 0.10 mm−1 |
| c = 14.6024 (4) Å | T = 100 (2) K |
| V = 966.37 (4) Å3 | Prism, colorless |
| Z = 4 | 0.30 × 0.20 × 0.10 mm |
| Bruker SMART APEX diffractometer | 986 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.039 |
| Monochromator: graphite | θmax = 27.5º |
| T = 100(2) K | θmin = 2.6º |
| ω scans | h = −8→9 |
| Absorption correction: None | k = −12→12 |
| 7349 measured reflections | l = −12→18 |
| 1164 independent reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.059 | H-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 reflections | Δρmax = 0.50 e Å−3 |
| 77 parameters | Δρmin = −0.50 e Å−3 |
| Primary atom site location: structure-invariant direct methods |
| C11H11NO3 | V = 966.37 (4) Å3 |
| Mr = 205.21 | Z = 4 |
| Orthorhombic, Pnma | Mo Kα |
| a = 7.0514 (2) Å | µ = 0.10 mm−1 |
| b = 9.3852 (2) Å | T = 100 (2) K |
| c = 14.6024 (4) Å | 0.30 × 0.20 × 0.10 mm |
| Bruker SMART APEX diffractometer | 1164 independent reflections |
| Absorption correction: None | 986 reflections with I > 2σ(I) |
| 7349 measured reflections | Rint = 0.039 |
| R[F2 > 2σ(F2)] = 0.059 | 77 parameters |
| wR(F2) = 0.206 | H-atom parameters constrained |
| S = 1.11 | Δρmax = 0.50 e Å−3 |
| 1164 reflections | Δρmin = −0.50 e Å−3 |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| O1 | 0.2012 (2) | 0.00647 (14) | 0.60172 (9) | 0.0229 (5) | |
| O2 | 0.3277 (3) | 0.2500 | 0.33669 (12) | 0.0161 (5) | |
| N1 | 0.2007 (4) | 0.2500 | 0.57847 (14) | 0.0167 (6) | |
| C1 | 0.2372 (3) | 0.17575 (18) | 0.89087 (12) | 0.0176 (5) | |
| H1 | 0.2434 | 0.1260 | 0.9475 | 0.021* | |
| C2 | 0.2281 (3) | 0.09866 (19) | 0.80904 (12) | 0.0168 (5) | |
| H2 | 0.2280 | −0.0026 | 0.8088 | 0.020* | |
| C3 | 0.2194 (3) | 0.17598 (18) | 0.72848 (11) | 0.0144 (5) | |
| C4 | 0.2072 (3) | 0.12658 (18) | 0.63197 (13) | 0.0171 (5) | |
| C5 | 0.1763 (4) | 0.2500 | 0.47961 (16) | 0.0176 (6) | |
| H5A | 0.1034 | 0.3354 | 0.4610 | 0.021* | 0.50 |
| H5B | 0.1034 | 0.1646 | 0.4610 | 0.021* | 0.50 |
| C6 | 0.3665 (4) | 0.2500 | 0.43155 (16) | 0.0175 (6) | |
| H6A | 0.4404 | 0.3357 | 0.4486 | 0.021* | 0.50 |
| H6B | 0.4404 | 0.1643 | 0.4486 | 0.021* | 0.50 |
| C7 | 0.4974 (4) | 0.2500 | 0.28287 (17) | 0.0210 (7) | |
| H7A | 0.4642 | 0.2500 | 0.2177 | 0.031* | |
| H7B | 0.5721 | 0.1647 | 0.2970 | 0.031* | 0.50 |
| H7C | 0.5721 | 0.3353 | 0.2970 | 0.031* | 0.50 |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0377 (10) | 0.0142 (8) | 0.0166 (8) | 0.0009 (6) | −0.0011 (6) | −0.0037 (5) |
| O2 | 0.0210 (11) | 0.0178 (9) | 0.0093 (9) | 0.000 | 0.0003 (7) | 0.000 |
| N1 | 0.0282 (14) | 0.0143 (11) | 0.0075 (10) | 0.000 | 0.0000 (8) | 0.000 |
| C1 | 0.0240 (10) | 0.0185 (10) | 0.0102 (9) | 0.0008 (7) | 0.0016 (6) | 0.0018 (6) |
| C2 | 0.0237 (11) | 0.0134 (8) | 0.0133 (9) | −0.0006 (7) | 0.0001 (7) | 0.0017 (6) |
| C3 | 0.0189 (10) | 0.0142 (9) | 0.0101 (9) | 0.0001 (7) | 0.0003 (6) | −0.0012 (6) |
| C4 | 0.0258 (11) | 0.0133 (9) | 0.0121 (9) | 0.0011 (7) | 0.0006 (7) | 0.0004 (6) |
| C5 | 0.0220 (14) | 0.0216 (12) | 0.0091 (12) | 0.000 | −0.0024 (9) | 0.000 |
| C6 | 0.0239 (15) | 0.0197 (11) | 0.0088 (12) | 0.000 | −0.0011 (9) | 0.000 |
| C7 | 0.0284 (17) | 0.0196 (12) | 0.0149 (12) | 0.000 | 0.0043 (11) | 0.000 |
| O1—C4 | 1.211 (2) | C3—C3i | 1.389 (3) |
| O2—C6 | 1.412 (3) | C3—C4 | 1.486 (2) |
| O2—C7 | 1.432 (3) | C5—C6 | 1.514 (4) |
| N1—C4 | 1.398 (2) | C5—H5A | 0.9900 |
| N1—C4i | 1.398 (2) | C5—H5B | 0.9900 |
| N1—C5 | 1.454 (3) | C6—H6A | 0.9900 |
| C1—C1i | 1.394 (3) | C6—H6B | 0.9900 |
| C1—C2 | 1.398 (2) | C7—H7A | 0.9800 |
| C1—H1 | 0.9500 | C7—H7B | 0.9800 |
| C2—C3 | 1.384 (2) | C7—H7C | 0.9800 |
| C2—H2 | 0.9500 | ||
| C6—O2—C7 | 112.1 (2) | N1—C5—H5A | 109.5 |
| C4—N1—C4i | 111.9 (2) | C6—C5—H5A | 109.5 |
| C4—N1—C5 | 123.97 (11) | N1—C5—H5B | 109.5 |
| C4i—N1—C5 | 123.97 (11) | C6—C5—H5B | 109.5 |
| C1i—C1—C2 | 121.16 (10) | H5A—C5—H5B | 108.1 |
| C1i—C1—H1 | 119.4 | O2—C6—C5 | 106.5 (2) |
| C2—C1—H1 | 119.4 | O2—C6—H6A | 110.4 |
| C3—C2—C1 | 117.21 (17) | C5—C6—H6A | 110.4 |
| C3—C2—H2 | 121.4 | O2—C6—H6B | 110.4 |
| C1—C2—H2 | 121.4 | C5—C6—H6B | 110.4 |
| C2—C3—C3i | 121.63 (11) | H6A—C6—H6B | 108.6 |
| C2—C3—C4 | 130.19 (16) | O2—C7—H7A | 109.5 |
| C3i—C3—C4 | 108.18 (9) | O2—C7—H7B | 109.5 |
| O1—C4—N1 | 124.48 (17) | H7A—C7—H7B | 109.5 |
| O1—C4—C3 | 129.64 (16) | O2—C7—H7C | 109.5 |
| N1—C4—C3 | 105.87 (15) | H7A—C7—H7C | 109.5 |
| N1—C5—C6 | 110.8 (2) | H7B—C7—H7C | 109.5 |
| C1i—C1—C2—C3 | 0.1 (2) | C3i—C3—C4—O1 | −179.02 (19) |
| C1—C2—C3—C3i | −0.1 (2) | C2—C3—C4—N1 | 179.5 (2) |
| C1—C2—C3—C4 | −179.47 (19) | C3i—C3—C4—N1 | 0.07 (17) |
| C4i—N1—C4—O1 | 179.03 (13) | C4—N1—C5—C6 | −92.3 (2) |
| C5—N1—C4—O1 | 3.2 (4) | C4i—N1—C5—C6 | 92.3 (2) |
| C4i—N1—C4—C3 | −0.1 (3) | C7—O2—C6—C5 | 180.0 |
| C5—N1—C4—C3 | −176.0 (2) | N1—C5—C6—O2 | 180.0 |
| C2—C3—C4—O1 | 0.5 (4) |
| Symmetry codes: (i) x, −y+1/2, z. |
We thank the SAGA grant (06–02-03–0147) for supporting this study, and the University of Malaya for the purchase of the diffractometer.
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Westrip, S. P. (2008). publCIF. In preparation.
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).