N-(2-Methoxy­phen­yl)phthalimide

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

doi:10.1107/S1600536809032826

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2218

doi:10.1107/S1600536809032826

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N-(2-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 54.2 (1)°.

Related literature

For the crystal structures of N-(phenyl)phthalimides, see: Izotova et al. (2009 ); Magomedova et al. (1980 ). For that of the 2-ethyl-substituted derivative, see: Fan et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₁NO₃
M_r = 253.25
Monoclinic, P 2₁ /n
a = 11.8505 (2) Å
b = 6.6903 (1) Å
c = 15.3264 (3) Å
β = 106.258 (1)°
V = 1166.54 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 123 K
0.28 × 0.16 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
10672 measured reflections
2682 independent reflections
2190 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.098
S = 1.03
2682 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 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/S1600536809032826/bt5039sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032826/bt5039Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of N-(phenyl)phthalimides, see: Izotova et al. (2009); Magomedova et al. (1980). For that of the 2-ethyl-substituted derivative, see: Fan et al. (2008).

Experimental top

Phthalic anhydride (5.00 g, 33.8 mmol) and 4-methoxyaniline (4.99 g, 40.5 mmol) were heated in acetic acid (15 ml) for 4 h. The mixture was cooled and then poured into water. The solid that separated was collected and recrystallized from ethanol in 90% 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-(2-Methoxyphenyl)phthalimide top

Crystal data top

C₁₅H₁₁NO₃	F(000) = 528
M_r = 253.25	D_x = 1.442 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3112 reflections
a = 11.8505 (2) Å	θ = 2.5–28.3°
b = 6.6903 (1) Å	µ = 0.10 mm⁻¹
c = 15.3264 (3) Å	T = 123 K
β = 106.258 (1)°	Irregular, colorless
V = 1166.54 (3) Å³	0.28 × 0.16 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2190 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −14→15
10672 measured reflections	k = −8→8
2682 independent reflections	l = −19→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0506P)² + 0.3213P] where P = (F_o² + 2F_c²)/3
2682 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₁NO₃	V = 1166.54 (3) Å³
M_r = 253.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8505 (2) Å	µ = 0.10 mm⁻¹
b = 6.6903 (1) Å	T = 123 K
c = 15.3264 (3) Å	0.28 × 0.16 × 0.04 mm
β = 106.258 (1)°

Data collection top

Bruker SMART APEX diffractometer	2190 reflections with I > 2σ(I)
10672 measured reflections	R_int = 0.028
2682 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.27 e Å⁻³
2682 reflections	Δρ_min = −0.22 e Å⁻³
173 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.76144 (8)	0.26041 (14)	0.47272 (6)	0.0232 (2)
O2	0.74087 (8)	0.35172 (14)	0.76449 (6)	0.0242 (2)
O3	0.89049 (8)	0.63238 (14)	0.56474 (6)	0.0240 (2)
N1	0.78134 (9)	0.32357 (16)	0.62507 (7)	0.0183 (2)
C1	0.71795 (11)	0.28292 (18)	0.53464 (8)	0.0177 (3)
C2	0.59283 (11)	0.26801 (17)	0.53474 (8)	0.0168 (3)
C3	0.49248 (11)	0.23766 (18)	0.46394 (9)	0.0187 (3)
H3	0.4962	0.2240	0.4031	0.022*
C4	0.38571 (11)	0.22777 (19)	0.48501 (9)	0.0205 (3)
H4	0.3149	0.2111	0.4376	0.025*
C5	0.38127 (11)	0.24202 (19)	0.57471 (9)	0.0227 (3)
H5	0.3075	0.2333	0.5875	0.027*
C6	0.48287 (11)	0.26884 (19)	0.64603 (9)	0.0203 (3)
H6	0.4801	0.2758	0.7073	0.024*
C7	0.58786 (11)	0.28491 (18)	0.62405 (8)	0.0178 (3)
C8	0.70848 (11)	0.32285 (18)	0.68350 (8)	0.0180 (3)
C9	0.90625 (10)	0.34589 (19)	0.65589 (8)	0.0183 (3)
C10	0.96165 (11)	0.50402 (19)	0.62429 (8)	0.0187 (3)
C11	1.08374 (11)	0.5197 (2)	0.65517 (8)	0.0226 (3)
H11	1.1233	0.6222	0.6324	0.027*
C12	1.14739 (12)	0.3852 (2)	0.71924 (9)	0.0251 (3)
H12	1.2304	0.3983	0.7409	0.030*
C13	1.09199 (12)	0.2325 (2)	0.75213 (9)	0.0242 (3)
H13	1.1362	0.1429	0.7968	0.029*
C14	0.97095 (11)	0.2121 (2)	0.71899 (9)	0.0217 (3)
H14	0.9323	0.1054	0.7398	0.026*
C15	0.94409 (12)	0.8082 (2)	0.54130 (10)	0.0254 (3)
H15A	0.9847	0.8806	0.5968	0.038*
H15B	0.8835	0.8942	0.5026	0.038*
H15C	1.0009	0.7703	0.5084	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0218 (5)	0.0299 (5)	0.0200 (5)	−0.0019 (4)	0.0091 (4)	−0.0012 (4)
O2	0.0228 (5)	0.0319 (5)	0.0176 (5)	−0.0004 (4)	0.0051 (4)	−0.0019 (4)
O3	0.0189 (5)	0.0231 (5)	0.0292 (5)	−0.0019 (4)	0.0052 (4)	0.0068 (4)
N1	0.0151 (5)	0.0223 (6)	0.0175 (5)	−0.0013 (4)	0.0047 (4)	0.0012 (4)
C1	0.0196 (6)	0.0152 (6)	0.0183 (6)	−0.0002 (4)	0.0054 (5)	0.0018 (5)
C2	0.0174 (6)	0.0138 (6)	0.0199 (6)	0.0000 (4)	0.0066 (5)	0.0019 (4)
C3	0.0211 (6)	0.0160 (6)	0.0187 (6)	0.0010 (5)	0.0049 (5)	0.0006 (5)
C4	0.0173 (6)	0.0180 (6)	0.0240 (6)	0.0000 (5)	0.0019 (5)	0.0002 (5)
C5	0.0176 (6)	0.0235 (7)	0.0282 (7)	−0.0013 (5)	0.0084 (5)	−0.0013 (5)
C6	0.0198 (6)	0.0220 (7)	0.0205 (6)	−0.0007 (5)	0.0079 (5)	−0.0001 (5)
C7	0.0196 (6)	0.0151 (6)	0.0186 (6)	−0.0006 (5)	0.0053 (5)	0.0005 (5)
C8	0.0182 (6)	0.0161 (6)	0.0201 (6)	0.0010 (5)	0.0063 (5)	0.0017 (5)
C9	0.0148 (6)	0.0226 (6)	0.0177 (6)	−0.0009 (5)	0.0047 (5)	−0.0025 (5)
C10	0.0186 (6)	0.0209 (6)	0.0174 (6)	0.0003 (5)	0.0061 (5)	−0.0016 (5)
C11	0.0193 (6)	0.0259 (7)	0.0242 (6)	−0.0044 (5)	0.0089 (5)	−0.0016 (5)
C12	0.0155 (6)	0.0337 (8)	0.0256 (7)	−0.0005 (5)	0.0050 (5)	−0.0022 (6)
C13	0.0206 (7)	0.0296 (7)	0.0217 (6)	0.0042 (5)	0.0045 (5)	0.0029 (5)
C14	0.0214 (7)	0.0237 (7)	0.0212 (6)	0.0004 (5)	0.0080 (5)	0.0016 (5)
C15	0.0270 (7)	0.0205 (7)	0.0296 (7)	−0.0032 (5)	0.0097 (6)	0.0032 (5)

Geometric parameters (Å, º) top

O1—C1	1.2095 (15)	C6—C7	1.3812 (18)
O2—C8	1.2077 (15)	C6—H6	0.9500
O3—C10	1.3604 (15)	C7—C8	1.4862 (17)
O3—C15	1.4296 (16)	C9—C14	1.3818 (18)
N1—C1	1.4057 (16)	C9—C10	1.4010 (18)
N1—C8	1.4073 (16)	C10—C11	1.3946 (17)
N1—C9	1.4301 (15)	C11—C12	1.3885 (19)
C1—C2	1.4865 (17)	C11—H11	0.9500
C2—C3	1.3821 (17)	C12—C13	1.383 (2)
C2—C7	1.3910 (17)	C12—H12	0.9500
C3—C4	1.3923 (18)	C13—C14	1.3879 (18)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.3937 (18)	C14—H14	0.9500
C4—H4	0.9500	C15—H15A	0.9800
C5—C6	1.3927 (18)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800

C10—O3—C15	116.90 (10)	O2—C8—C7	129.18 (12)
C1—N1—C8	111.90 (10)	N1—C8—C7	105.46 (10)
C1—N1—C9	124.33 (10)	C14—C9—C10	120.61 (11)
C8—N1—C9	123.56 (10)	C14—C9—N1	118.93 (11)
O1—C1—N1	124.77 (12)	C10—C9—N1	120.43 (11)
O1—C1—C2	129.54 (11)	O3—C10—C11	124.71 (11)
N1—C1—C2	105.66 (10)	O3—C10—C9	116.50 (11)
C3—C2—C7	121.35 (11)	C11—C10—C9	118.79 (11)
C3—C2—C1	130.42 (11)	C12—C11—C10	119.85 (12)
C7—C2—C1	108.21 (11)	C12—C11—H11	120.1
C2—C3—C4	117.57 (12)	C10—C11—H11	120.1
C2—C3—H3	121.2	C13—C12—C11	121.12 (12)
C4—C3—H3	121.2	C13—C12—H12	119.4
C3—C4—C5	120.89 (12)	C11—C12—H12	119.4
C3—C4—H4	119.6	C12—C13—C14	119.12 (12)
C5—C4—H4	119.6	C12—C13—H13	120.4
C6—C5—C4	121.32 (12)	C14—C13—H13	120.4
C6—C5—H5	119.3	C9—C14—C13	120.42 (12)
C4—C5—H5	119.3	C9—C14—H14	119.8
C7—C6—C5	117.29 (12)	C13—C14—H14	119.8
C7—C6—H6	121.4	O3—C15—H15A	109.5
C5—C6—H6	121.4	O3—C15—H15B	109.5
C6—C7—C2	121.53 (11)	H15A—C15—H15B	109.5
C6—C7—C8	129.88 (12)	O3—C15—H15C	109.5
C2—C7—C8	108.59 (11)	H15A—C15—H15C	109.5
O2—C8—N1	125.34 (11)	H15B—C15—H15C	109.5

C8—N1—C1—O1	−174.23 (12)	C9—N1—C8—C7	−176.91 (11)
C9—N1—C1—O1	0.68 (19)	C6—C7—C8—O2	−1.5 (2)
C8—N1—C1—C2	3.86 (13)	C2—C7—C8—O2	177.74 (13)
C9—N1—C1—C2	178.77 (11)	C6—C7—C8—N1	179.86 (12)
O1—C1—C2—C3	−4.7 (2)	C2—C7—C8—N1	−0.90 (13)
N1—C1—C2—C3	177.31 (12)	C1—N1—C9—C14	−117.21 (13)
O1—C1—C2—C7	173.64 (12)	C8—N1—C9—C14	57.11 (17)
N1—C1—C2—C7	−4.33 (13)	C1—N1—C9—C10	64.41 (16)
C7—C2—C3—C4	1.02 (18)	C8—N1—C9—C10	−121.27 (13)
C1—C2—C3—C4	179.20 (12)	C15—O3—C10—C11	−7.96 (18)
C2—C3—C4—C5	−1.90 (18)	C15—O3—C10—C9	172.06 (11)
C3—C4—C5—C6	0.75 (19)	C14—C9—C10—O3	−177.71 (11)
C4—C5—C6—C7	1.31 (19)	N1—C9—C10—O3	0.64 (17)
C5—C6—C7—C2	−2.21 (19)	C14—C9—C10—C11	2.31 (18)
C5—C6—C7—C8	176.94 (12)	N1—C9—C10—C11	−179.34 (11)
C3—C2—C7—C6	1.07 (19)	O3—C10—C11—C12	177.10 (12)
C1—C2—C7—C6	−177.47 (11)	C9—C10—C11—C12	−2.92 (19)
C3—C2—C7—C8	−178.24 (11)	C10—C11—C12—C13	1.2 (2)
C1—C2—C7—C8	3.22 (13)	C11—C12—C13—C14	1.2 (2)
C1—N1—C8—O2	179.33 (12)	C10—C9—C14—C13	0.07 (19)
C9—N1—C8—O2	4.38 (19)	N1—C9—C14—C13	−178.31 (11)
C1—N1—C8—C7	−1.96 (13)	C12—C13—C14—C9	−1.8 (2)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO₃
M_r	253.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	11.8505 (2), 6.6903 (1), 15.3264 (3)
β (°)	106.258 (1)
V (Å³)	1166.54 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.16 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10672, 2682, 2190
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.03
No. of reflections	2682
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

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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