N-(2-Methoxy­ethyl)phthalimide

Sim, Y.L.; Ariffin, A.; Ng, S.W.

doi:10.1107/S1600536808013548

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1058

doi:10.1107/S1600536808013548

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N-(2-Methoxyethyl)phthalimide

Yoke Leng Sim,^a Azhar Ariffin ^a and Seik Weng Ng ^a ^*

^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 ); 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, 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)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 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 ).

Supporting information

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

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

checkCIF report

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.

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

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

C₁₁H₁₁NO₃	F(000) = 432
M_r = 205.21	D_x = 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 = 2.6–28.3°
b = 9.3852 (2) Å	µ = 0.10 mm⁻¹
c = 14.6024 (4) Å	T = 100 K
V = 966.37 (4) Å³	Prism, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX diffractometer	986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −8→9
7349 measured reflections	k = −12→12
1164 independent reflections	l = −12→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.206	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.1433P)² + 0.309P] where P = (F_o² + 2F_c²)/3
1164 reflections	(Δ/σ)_max = 0.001
77 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₁H₁₁NO₃	V = 966.37 (4) Å³
M_r = 205.21	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 7.0514 (2) Å	µ = 0.10 mm⁻¹
b = 9.3852 (2) Å	T = 100 K
c = 14.6024 (4) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX diffractometer	986 reflections with I > 2σ(I)
7349 measured reflections	R_int = 0.039
1164 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.206	H-atom parameters constrained
S = 1.11	Δρ_max = 0.50 e Å⁻³
1164 reflections	Δρ_min = −0.50 e Å⁻³
77 parameters

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

	x	y	z	U_iso*/U_eq	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 (Å²) top

	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, º) top

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 code: (i) x, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁NO₃
M_r	205.21
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	100
a, b, c (Å)	7.0514 (2), 9.3852 (2), 14.6024 (4)
V (Å³)	966.37 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7349, 1164, 986
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.206, 1.11
No. of reflections	1164
No. of parameters	77
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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