N-(4-Methoxy­phen­yl)phthalimide

Sim, Y.L.; Ariffin, A.; Khan, M.N.; Ng, S.W.

doi:10.1107/S1600536809032838

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2219

doi:10.1107/S1600536809032838

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N-(4-Methoxyphenyl)phthalimide

Yoke Ling Sim,^a Azhar Ariffin,^a Mohammad Niyaz Khan ^a and Seik Weng Ng ^a ^*

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

(Received 17 August 2009; accepted 18 August 2009; online 22 August 2009)

The phthalimide fused-ring system and the phenylene ring in the title compound, C₁₅H₁₁NO₃, are inclined at an angle of 60.0 (1)°.

Related literature

For the crystal structures of N-(phenyl)phthalimides, see: Izotova et al. (2009 ); Magomedova et al. (1980 ). For the 4-methyl-substituted derivative, see: Bocelli et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₁NO₃
M_r = 253.25
Monoclinic, P 2₁ /c
a = 18.6152 (5) Å
b = 3.8502 (1) Å
c = 16.3125 (4) Å
β = 96.704 (2)°
V = 1161.16 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 123 K
0.40 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
9965 measured reflections
2645 independent reflections
1927 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.104
S = 1.01
2645 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032838/bt5040sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032838/bt5040Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of N-(phenyl)phthalimides, see: Izotova et al. (2009); Magomedova et al. (1980). For the 4-methyl-substituted derivative, see: Bocelli et al. (1995).

Experimental top

Phthalic anhydride (1.83 g, 12.4 mmol) and 4-methoxyaniline (1.01 g, 8.24 mmol) were heated in acetic acid (10 ml) for 4 h. The mixture was cooled and then was poured into water. The solid that separated was collected and recrystallized from ethanol in 60% yield.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₅H₁₁NO₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

N-(4-Methoxyphenyl)phthalimide top

Crystal data top

C₁₅H₁₁NO₃	F(000) = 528
M_r = 253.25	D_x = 1.449 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2162 reflections
a = 18.6152 (5) Å	θ = 2.6–28.1°
b = 3.8502 (1) Å	µ = 0.10 mm⁻¹
c = 16.3125 (4) Å	T = 123 K
β = 96.704 (2)°	Colorless, prism
V = 1161.16 (5) Å³	0.40 × 0.06 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	1927 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 27.5°, θ_min = 1.1°
ω scans	h = −24→24
9965 measured reflections	k = −4→4
2645 independent reflections	l = −19→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0442P)² + 0.5469P] where P = (F_o² + 2F_c²)/3
2645 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₁NO₃	V = 1161.16 (5) Å³
M_r = 253.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.6152 (5) Å	µ = 0.10 mm⁻¹
b = 3.8502 (1) Å	T = 123 K
c = 16.3125 (4) Å	0.40 × 0.06 × 0.04 mm
β = 96.704 (2)°

Data collection top

Bruker SMART APEX diffractometer	1927 reflections with I > 2σ(I)
9965 measured reflections	R_int = 0.038
2645 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
2645 reflections	Δρ_min = −0.24 e Å⁻³
173 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.23040 (7)	0.2003 (4)	0.30862 (8)	0.0191 (3)
O1	0.13566 (6)	0.4704 (3)	0.36518 (7)	0.0265 (3)
O2	0.29659 (6)	−0.0742 (3)	0.21493 (7)	0.0249 (3)
O3	0.44516 (6)	0.1734 (3)	0.57594 (7)	0.0240 (3)
C1	0.16067 (8)	0.3406 (4)	0.30709 (10)	0.0195 (3)
C2	0.12587 (8)	0.2999 (4)	0.22082 (10)	0.0187 (3)
C3	0.05760 (8)	0.3925 (4)	0.18527 (10)	0.0214 (4)
H3	0.0239	0.4996	0.2167	0.026*
C4	0.04005 (9)	0.3230 (4)	0.10160 (10)	0.0234 (4)
H4	−0.0068	0.3803	0.0756	0.028*
C5	0.08989 (9)	0.1710 (4)	0.05523 (10)	0.0236 (4)
H5	0.0768	0.1297	−0.0020	0.028*
C6	0.15867 (9)	0.0785 (4)	0.09164 (10)	0.0211 (4)
H6	0.1929	−0.0255	0.0603	0.025*
C7	0.17521 (8)	0.1437 (4)	0.17481 (10)	0.0185 (3)
C8	0.24232 (8)	0.0711 (4)	0.23055 (10)	0.0192 (3)
C9	0.28401 (8)	0.1935 (4)	0.37938 (10)	0.0191 (3)
C10	0.26872 (8)	0.0433 (4)	0.45236 (10)	0.0201 (3)
H10	0.2223	−0.0543	0.4559	0.024*
C11	0.32090 (8)	0.0343 (4)	0.52048 (10)	0.0206 (3)
H11	0.3102	−0.0641	0.5711	0.025*
C12	0.38907 (8)	0.1716 (4)	0.51360 (10)	0.0194 (3)
C13	0.40427 (8)	0.3237 (4)	0.44008 (10)	0.0213 (4)
H13	0.4509	0.4182	0.4360	0.026*
C14	0.35172 (8)	0.3369 (4)	0.37337 (10)	0.0211 (4)
H14	0.3617	0.4435	0.3234	0.025*
C15	0.43407 (9)	0.0139 (5)	0.65216 (10)	0.0255 (4)
H15A	0.4789	0.0251	0.6901	0.038*
H15B	0.4202	−0.2295	0.6424	0.038*
H15C	0.3955	0.1362	0.6764	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0191 (6)	0.0228 (7)	0.0162 (7)	0.0004 (5)	0.0050 (5)	−0.0009 (5)
O1	0.0258 (6)	0.0341 (7)	0.0207 (6)	0.0032 (5)	0.0080 (5)	−0.0052 (5)
O2	0.0225 (6)	0.0290 (7)	0.0244 (6)	0.0061 (5)	0.0075 (5)	−0.0012 (5)
O3	0.0214 (6)	0.0304 (7)	0.0197 (6)	−0.0022 (5)	0.0010 (5)	0.0021 (5)
C1	0.0199 (8)	0.0188 (8)	0.0210 (8)	−0.0010 (6)	0.0075 (6)	0.0012 (6)
C2	0.0217 (8)	0.0164 (8)	0.0191 (8)	−0.0019 (6)	0.0070 (6)	0.0010 (6)
C3	0.0208 (8)	0.0205 (8)	0.0243 (9)	0.0004 (6)	0.0082 (7)	0.0021 (7)
C4	0.0210 (8)	0.0231 (9)	0.0258 (9)	−0.0016 (7)	0.0021 (7)	0.0047 (7)
C5	0.0287 (9)	0.0231 (9)	0.0188 (8)	−0.0032 (7)	0.0022 (7)	0.0013 (7)
C6	0.0254 (8)	0.0193 (8)	0.0195 (8)	−0.0009 (7)	0.0066 (6)	−0.0001 (7)
C7	0.0212 (8)	0.0161 (8)	0.0194 (8)	−0.0021 (6)	0.0072 (6)	0.0019 (6)
C8	0.0226 (8)	0.0172 (8)	0.0190 (8)	−0.0014 (6)	0.0071 (6)	0.0010 (6)
C9	0.0200 (8)	0.0184 (8)	0.0191 (8)	0.0018 (6)	0.0032 (6)	−0.0019 (6)
C10	0.0194 (8)	0.0205 (8)	0.0213 (9)	−0.0021 (6)	0.0068 (6)	−0.0010 (6)
C11	0.0244 (8)	0.0202 (8)	0.0181 (8)	−0.0001 (6)	0.0064 (6)	0.0005 (6)
C12	0.0203 (8)	0.0174 (8)	0.0204 (8)	0.0023 (6)	0.0028 (6)	−0.0024 (6)
C13	0.0196 (8)	0.0217 (9)	0.0238 (9)	−0.0002 (7)	0.0075 (6)	−0.0003 (7)
C14	0.0237 (8)	0.0211 (8)	0.0200 (8)	−0.0004 (7)	0.0078 (6)	0.0012 (6)
C15	0.0291 (9)	0.0274 (10)	0.0196 (9)	−0.0009 (7)	0.0017 (7)	0.0022 (7)

Geometric parameters (Å, º) top

N1—C1	1.4034 (19)	C6—C7	1.379 (2)
N1—C8	1.409 (2)	C6—H6	0.9500
N1—C9	1.435 (2)	C7—C8	1.483 (2)
O1—C1	1.2114 (19)	C9—C10	1.383 (2)
O2—C8	1.2080 (18)	C9—C14	1.390 (2)
O3—C12	1.3699 (19)	C10—C11	1.388 (2)
O3—C15	1.4232 (19)	C10—H10	0.9500
C1—C2	1.487 (2)	C11—C12	1.391 (2)
C2—C3	1.381 (2)	C11—H11	0.9500
C2—C7	1.389 (2)	C12—C13	1.393 (2)
C3—C4	1.392 (2)	C13—C14	1.377 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.392 (2)	C14—H14	0.9500
C4—H4	0.9500	C15—H15A	0.9800
C5—C6	1.393 (2)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800

C1—N1—C8	111.27 (13)	O2—C8—C7	128.56 (15)
C1—N1—C9	125.17 (13)	N1—C8—C7	106.11 (13)
C8—N1—C9	123.54 (13)	C10—C9—C14	120.42 (15)
C12—O3—C15	118.08 (12)	C10—C9—N1	120.41 (14)
O1—C1—N1	125.74 (15)	C14—C9—N1	119.17 (14)
O1—C1—C2	128.24 (15)	C9—C10—C11	120.29 (14)
N1—C1—C2	106.02 (13)	C9—C10—H10	119.9
C3—C2—C7	121.28 (15)	C11—C10—H10	119.9
C3—C2—C1	130.39 (14)	C10—C11—C12	119.05 (15)
C7—C2—C1	108.33 (14)	C10—C11—H11	120.5
C2—C3—C4	117.47 (15)	C12—C11—H11	120.5
C2—C3—H3	121.3	O3—C12—C11	124.43 (14)
C4—C3—H3	121.3	O3—C12—C13	115.03 (14)
C3—C4—C5	121.23 (15)	C11—C12—C13	120.53 (15)
C3—C4—H4	119.4	C14—C13—C12	119.94 (14)
C5—C4—H4	119.4	C14—C13—H13	120.0
C4—C5—C6	120.88 (16)	C12—C13—H13	120.0
C4—C5—H5	119.6	C13—C14—C9	119.75 (15)
C6—C5—H5	119.6	C13—C14—H14	120.1
C7—C6—C5	117.48 (15)	C9—C14—H14	120.1
C7—C6—H6	121.3	O3—C15—H15A	109.5
C5—C6—H6	121.3	O3—C15—H15B	109.5
C6—C7—C2	121.64 (15)	H15A—C15—H15B	109.5
C6—C7—C8	130.11 (14)	O3—C15—H15C	109.5
C2—C7—C8	108.24 (14)	H15A—C15—H15C	109.5
O2—C8—N1	125.32 (15)	H15B—C15—H15C	109.5

C8—N1—C1—O1	−179.83 (16)	C9—N1—C8—C7	−177.28 (14)
C9—N1—C1—O1	−1.1 (3)	C6—C7—C8—O2	−2.9 (3)
C8—N1—C1—C2	−0.56 (17)	C2—C7—C8—O2	176.86 (16)
C9—N1—C1—C2	178.14 (14)	C6—C7—C8—N1	178.40 (16)
O1—C1—C2—C3	−0.9 (3)	C2—C7—C8—N1	−1.81 (17)
N1—C1—C2—C3	179.88 (16)	C1—N1—C9—C10	55.6 (2)
O1—C1—C2—C7	178.63 (16)	C8—N1—C9—C10	−125.84 (17)
N1—C1—C2—C7	−0.62 (17)	C1—N1—C9—C14	−125.02 (17)
C7—C2—C3—C4	0.1 (2)	C8—N1—C9—C14	53.5 (2)
C1—C2—C3—C4	179.55 (16)	C14—C9—C10—C11	0.1 (2)
C2—C3—C4—C5	−1.0 (2)	N1—C9—C10—C11	179.42 (14)
C3—C4—C5—C6	1.0 (3)	C9—C10—C11—C12	−1.4 (2)
C4—C5—C6—C7	−0.1 (2)	C15—O3—C12—C11	2.2 (2)
C5—C6—C7—C2	−0.9 (2)	C15—O3—C12—C13	−178.34 (14)
C5—C6—C7—C8	178.91 (16)	C10—C11—C12—O3	−179.02 (14)
C3—C2—C7—C6	0.9 (2)	C10—C11—C12—C13	1.6 (2)
C1—C2—C7—C6	−178.69 (14)	O3—C12—C13—C14	−179.87 (14)
C3—C2—C7—C8	−178.96 (14)	C11—C12—C13—C14	−0.4 (2)
C1—C2—C7—C8	1.49 (17)	C12—C13—C14—C9	−0.9 (2)
C1—N1—C8—O2	−177.28 (15)	C10—C9—C14—C13	1.1 (2)
C9—N1—C8—O2	4.0 (2)	N1—C9—C14—C13	−178.24 (14)
C1—N1—C8—C7	1.44 (17)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO₃
M_r	253.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	18.6152 (5), 3.8502 (1), 16.3125 (4)
β (°)	96.704 (2)
V (Å³)	1161.16 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.06 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9965, 2645, 1927
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.104, 1.01
No. of reflections	2645
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.24

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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