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N-(4-Meth­oxy­phen­yl)phthalimide

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[Izotova, L. Y., Ashurov, J. M., Ibragimov, B. T. & Weber, E. (2009). Acta Cryst. E65, o658.]); Magomedova et al. (1980[Magomedova, N. S., Dzyabchenko, A. V., Zavodnik, V. E. & Belskii, V. K. (1980). Cryst. Struct. Commun. 9, 713-715.]). For the 4-methyl-substituted derivative, see: Bocelli et al. (1995[Bocelli, G., Cantoni, A. & Cozzini, P. (1995). Acta Cryst. C51, 2372-2374.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11NO3

  • Mr = 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)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.104

  • S = 1.01

  • 2645 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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.

Refinement top

H-atoms were placed in calculated positions (C—H 0.95 or 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C) or 1.5U(Cmethyl).

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
[Figure 1] 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
C15H11NO3F(000) = 528
Mr = 253.25Dx = 1.449 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2162 reflections
a = 18.6152 (5) Åθ = 2.6–28.1°
b = 3.8502 (1) ŵ = 0.10 mm1
c = 16.3125 (4) ÅT = 123 K
β = 96.704 (2)°Colorless, prism
V = 1161.16 (5) Å30.40 × 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 tubeRint = 0.038
Graphite monochromatorθmax = 27.5°, θmin = 1.1°
ω scansh = 2424
9965 measured reflectionsk = 44
2645 independent reflectionsl = 1921
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0442P)2 + 0.5469P]
where P = (Fo2 + 2Fc2)/3
2645 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C15H11NO3V = 1161.16 (5) Å3
Mr = 253.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.6152 (5) ŵ = 0.10 mm1
b = 3.8502 (1) ÅT = 123 K
c = 16.3125 (4) Å0.40 × 0.06 × 0.04 mm
β = 96.704 (2)°
Data collection top
Bruker SMART APEX
diffractometer
1927 reflections with I > 2σ(I)
9965 measured reflectionsRint = 0.038
2645 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å3
2645 reflectionsΔρmin = 0.24 e Å3
173 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.23040 (7)0.2003 (4)0.30862 (8)0.0191 (3)
O10.13566 (6)0.4704 (3)0.36518 (7)0.0265 (3)
O20.29659 (6)0.0742 (3)0.21493 (7)0.0249 (3)
O30.44516 (6)0.1734 (3)0.57594 (7)0.0240 (3)
C10.16067 (8)0.3406 (4)0.30709 (10)0.0195 (3)
C20.12587 (8)0.2999 (4)0.22082 (10)0.0187 (3)
C30.05760 (8)0.3925 (4)0.18527 (10)0.0214 (4)
H30.02390.49960.21670.026*
C40.04005 (9)0.3230 (4)0.10160 (10)0.0234 (4)
H40.00680.38030.07560.028*
C50.08989 (9)0.1710 (4)0.05523 (10)0.0236 (4)
H50.07680.12970.00200.028*
C60.15867 (9)0.0785 (4)0.09164 (10)0.0211 (4)
H60.19290.02550.06030.025*
C70.17521 (8)0.1437 (4)0.17481 (10)0.0185 (3)
C80.24232 (8)0.0711 (4)0.23055 (10)0.0192 (3)
C90.28401 (8)0.1935 (4)0.37938 (10)0.0191 (3)
C100.26872 (8)0.0433 (4)0.45236 (10)0.0201 (3)
H100.22230.05430.45590.024*
C110.32090 (8)0.0343 (4)0.52048 (10)0.0206 (3)
H110.31020.06410.57110.025*
C120.38907 (8)0.1716 (4)0.51360 (10)0.0194 (3)
C130.40427 (8)0.3237 (4)0.44008 (10)0.0213 (4)
H130.45090.41820.43600.026*
C140.35172 (8)0.3369 (4)0.37337 (10)0.0211 (4)
H140.36170.44350.32340.025*
C150.43407 (9)0.0139 (5)0.65216 (10)0.0255 (4)
H15A0.47890.02510.69010.038*
H15B0.42020.22950.64240.038*
H15C0.39550.13620.67640.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0191 (6)0.0228 (7)0.0162 (7)0.0004 (5)0.0050 (5)0.0009 (5)
O10.0258 (6)0.0341 (7)0.0207 (6)0.0032 (5)0.0080 (5)0.0052 (5)
O20.0225 (6)0.0290 (7)0.0244 (6)0.0061 (5)0.0075 (5)0.0012 (5)
O30.0214 (6)0.0304 (7)0.0197 (6)0.0022 (5)0.0010 (5)0.0021 (5)
C10.0199 (8)0.0188 (8)0.0210 (8)0.0010 (6)0.0075 (6)0.0012 (6)
C20.0217 (8)0.0164 (8)0.0191 (8)0.0019 (6)0.0070 (6)0.0010 (6)
C30.0208 (8)0.0205 (8)0.0243 (9)0.0004 (6)0.0082 (7)0.0021 (7)
C40.0210 (8)0.0231 (9)0.0258 (9)0.0016 (7)0.0021 (7)0.0047 (7)
C50.0287 (9)0.0231 (9)0.0188 (8)0.0032 (7)0.0022 (7)0.0013 (7)
C60.0254 (8)0.0193 (8)0.0195 (8)0.0009 (7)0.0066 (6)0.0001 (7)
C70.0212 (8)0.0161 (8)0.0194 (8)0.0021 (6)0.0072 (6)0.0019 (6)
C80.0226 (8)0.0172 (8)0.0190 (8)0.0014 (6)0.0071 (6)0.0010 (6)
C90.0200 (8)0.0184 (8)0.0191 (8)0.0018 (6)0.0032 (6)0.0019 (6)
C100.0194 (8)0.0205 (8)0.0213 (9)0.0021 (6)0.0068 (6)0.0010 (6)
C110.0244 (8)0.0202 (8)0.0181 (8)0.0001 (6)0.0064 (6)0.0005 (6)
C120.0203 (8)0.0174 (8)0.0204 (8)0.0023 (6)0.0028 (6)0.0024 (6)
C130.0196 (8)0.0217 (9)0.0238 (9)0.0002 (7)0.0075 (6)0.0003 (7)
C140.0237 (8)0.0211 (8)0.0200 (8)0.0004 (7)0.0078 (6)0.0012 (6)
C150.0291 (9)0.0274 (10)0.0196 (9)0.0009 (7)0.0017 (7)0.0022 (7)
Geometric parameters (Å, º) top
N1—C11.4034 (19)C6—C71.379 (2)
N1—C81.409 (2)C6—H60.9500
N1—C91.435 (2)C7—C81.483 (2)
O1—C11.2114 (19)C9—C101.383 (2)
O2—C81.2080 (18)C9—C141.390 (2)
O3—C121.3699 (19)C10—C111.388 (2)
O3—C151.4232 (19)C10—H100.9500
C1—C21.487 (2)C11—C121.391 (2)
C2—C31.381 (2)C11—H110.9500
C2—C71.389 (2)C12—C131.393 (2)
C3—C41.392 (2)C13—C141.377 (2)
C3—H30.9500C13—H130.9500
C4—C51.392 (2)C14—H140.9500
C4—H40.9500C15—H15A0.9800
C5—C61.393 (2)C15—H15B0.9800
C5—H50.9500C15—H15C0.9800
C1—N1—C8111.27 (13)O2—C8—C7128.56 (15)
C1—N1—C9125.17 (13)N1—C8—C7106.11 (13)
C8—N1—C9123.54 (13)C10—C9—C14120.42 (15)
C12—O3—C15118.08 (12)C10—C9—N1120.41 (14)
O1—C1—N1125.74 (15)C14—C9—N1119.17 (14)
O1—C1—C2128.24 (15)C9—C10—C11120.29 (14)
N1—C1—C2106.02 (13)C9—C10—H10119.9
C3—C2—C7121.28 (15)C11—C10—H10119.9
C3—C2—C1130.39 (14)C10—C11—C12119.05 (15)
C7—C2—C1108.33 (14)C10—C11—H11120.5
C2—C3—C4117.47 (15)C12—C11—H11120.5
C2—C3—H3121.3O3—C12—C11124.43 (14)
C4—C3—H3121.3O3—C12—C13115.03 (14)
C3—C4—C5121.23 (15)C11—C12—C13120.53 (15)
C3—C4—H4119.4C14—C13—C12119.94 (14)
C5—C4—H4119.4C14—C13—H13120.0
C4—C5—C6120.88 (16)C12—C13—H13120.0
C4—C5—H5119.6C13—C14—C9119.75 (15)
C6—C5—H5119.6C13—C14—H14120.1
C7—C6—C5117.48 (15)C9—C14—H14120.1
C7—C6—H6121.3O3—C15—H15A109.5
C5—C6—H6121.3O3—C15—H15B109.5
C6—C7—C2121.64 (15)H15A—C15—H15B109.5
C6—C7—C8130.11 (14)O3—C15—H15C109.5
C2—C7—C8108.24 (14)H15A—C15—H15C109.5
O2—C8—N1125.32 (15)H15B—C15—H15C109.5
C8—N1—C1—O1179.83 (16)C9—N1—C8—C7177.28 (14)
C9—N1—C1—O11.1 (3)C6—C7—C8—O22.9 (3)
C8—N1—C1—C20.56 (17)C2—C7—C8—O2176.86 (16)
C9—N1—C1—C2178.14 (14)C6—C7—C8—N1178.40 (16)
O1—C1—C2—C30.9 (3)C2—C7—C8—N11.81 (17)
N1—C1—C2—C3179.88 (16)C1—N1—C9—C1055.6 (2)
O1—C1—C2—C7178.63 (16)C8—N1—C9—C10125.84 (17)
N1—C1—C2—C70.62 (17)C1—N1—C9—C14125.02 (17)
C7—C2—C3—C40.1 (2)C8—N1—C9—C1453.5 (2)
C1—C2—C3—C4179.55 (16)C14—C9—C10—C110.1 (2)
C2—C3—C4—C51.0 (2)N1—C9—C10—C11179.42 (14)
C3—C4—C5—C61.0 (3)C9—C10—C11—C121.4 (2)
C4—C5—C6—C70.1 (2)C15—O3—C12—C112.2 (2)
C5—C6—C7—C20.9 (2)C15—O3—C12—C13178.34 (14)
C5—C6—C7—C8178.91 (16)C10—C11—C12—O3179.02 (14)
C3—C2—C7—C60.9 (2)C10—C11—C12—C131.6 (2)
C1—C2—C7—C6178.69 (14)O3—C12—C13—C14179.87 (14)
C3—C2—C7—C8178.96 (14)C11—C12—C13—C140.4 (2)
C1—C2—C7—C81.49 (17)C12—C13—C14—C90.9 (2)
C1—N1—C8—O2177.28 (15)C10—C9—C14—C131.1 (2)
C9—N1—C8—O24.0 (2)N1—C9—C14—C13178.24 (14)
C1—N1—C8—C71.44 (17)

Experimental details

Crystal data
Chemical formulaC15H11NO3
Mr253.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)123
a, b, c (Å)18.6152 (5), 3.8502 (1), 16.3125 (4)
β (°) 96.704 (2)
V3)1161.16 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.06 × 0.04
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9965, 2645, 1927
Rint0.038
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.104, 1.01
No. of reflections2645
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBocelli, G., Cantoni, A. & Cozzini, P. (1995). Acta Cryst. C51, 2372–2374.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationIzotova, L. Y., Ashurov, J. M., Ibragimov, B. T. & Weber, E. (2009). Acta Cryst. E65, o658.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMagomedova, N. S., Dzyabchenko, A. V., Zavodnik, V. E. & Belskii, V. K. (1980). Cryst. Struct. Commun. 9, 713–715.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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