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

Experimental

Crystal data

• C₁₁H₁₁NO₃

• M _r = 205.21

• Orthorhombic,

• a = 7.0514 (2) Å

• b = 9.3852 (2) Å

• c = 14.6024 (4) Å

• V = 966.37 (4) ų

• 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

• Δρ_max = 0.50 e Å⁻³

• Δρ_min = −0.50 e Å⁻³

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

Supplementary Material

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

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

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

Data collection

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

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

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

	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

Atomic displacement parameters (Ų)

	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

Geometric parameters (Å, °)

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.