PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2219.
Published online 2009 August 22. doi:  10.1107/S1600536809032838
PMCID: PMC2970078

N-(4-Methoxy­phen­yl)phthalimide

Abstract

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 [triangle]); Magomedova et al. (1980 [triangle]). For the 4-methyl-substituted derivative, see: Bocelli et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2219-scheme1.jpg

Experimental

Crystal data

  • C15H11NO3
  • M r = 253.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2219-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 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 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

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

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

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

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

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).

Figures

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

Crystal data

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

Bruker SMART APEX diffractometer1927 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
graphiteθmax = 27.5°, θmin = 1.1°
ω scansh = −24→24
9965 measured reflectionsk = −4→4
2645 independent reflectionsl = −19→21

Refinement

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 = 1.01w = 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

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

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)
H4−0.00680.38030.07560.028*
C50.08989 (9)0.1710 (4)0.05523 (10)0.0236 (4)
H50.07680.1297−0.00200.028*
C60.15867 (9)0.0785 (4)0.09164 (10)0.0211 (4)
H60.1929−0.02550.06030.025*
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)
H100.2223−0.05430.45590.024*
C110.32090 (8)0.0343 (4)0.52048 (10)0.0206 (3)
H110.3102−0.06410.57110.025*
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*
H15B0.4202−0.22950.64240.038*
H15C0.39550.13620.67640.038*

Atomic displacement parameters (Å2)

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, °)

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—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—O2176.86 (16)
C9—N1—C1—C2178.14 (14)C6—C7—C8—N1178.40 (16)
O1—C1—C2—C3−0.9 (3)C2—C7—C8—N1−1.81 (17)
N1—C1—C2—C3179.88 (16)C1—N1—C9—C1055.6 (2)
O1—C1—C2—C7178.63 (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—C40.1 (2)C8—N1—C9—C1453.5 (2)
C1—C2—C3—C4179.55 (16)C14—C9—C10—C110.1 (2)
C2—C3—C4—C5−1.0 (2)N1—C9—C10—C11179.42 (14)
C3—C4—C5—C61.0 (3)C9—C10—C11—C12−1.4 (2)
C4—C5—C6—C7−0.1 (2)C15—O3—C12—C112.2 (2)
C5—C6—C7—C2−0.9 (2)C15—O3—C12—C13−178.34 (14)
C5—C6—C7—C8178.91 (16)C10—C11—C12—O3−179.02 (14)
C3—C2—C7—C60.9 (2)C10—C11—C12—C131.6 (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—C81.49 (17)C12—C13—C14—C9−0.9 (2)
C1—N1—C8—O2−177.28 (15)C10—C9—C14—C131.1 (2)
C9—N1—C8—O24.0 (2)N1—C9—C14—C13−178.24 (14)
C1—N1—C8—C71.44 (17)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5040).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bocelli, G., Cantoni, A. & Cozzini, P. (1995). Acta Cryst. C51, 2372–2374.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Izotova, L. Y., Ashurov, J. M., Ibragimov, B. T. & Weber, E. (2009). Acta Cryst. E65, o658. [PMC free article] [PubMed]
  • Magomedova, N. S., Dzyabchenko, A. V., Zavodnik, V. E. & Belskii, V. K. (1980). Cryst. Struct. Commun.9, 713–715.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography