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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1699.
Published online 2008 August 6. doi:  10.1107/S1600536808020448
PMCID: PMC2960657

N-(2-Ethyl­phen­yl)phthalimide

Abstract

In the title compound, C16H13NO2, the phthalimide and benzene ring systems form a dihedral angle of 77.2 (1)°.

Related literature

The crystal structures of a number of phenyl-substituted N-phenyl­phthalimides have been reported. For the 2-tolyl analogue, see: Bocelli & Cantoni (1989 [triangle]). For the 2,4-dimethyl­phenyl analogue, see: Magnomedova et al. (1980 [triangle]); Shahzadi et al. (2006 [triangle]). For the 2,6-dimethyl­phenyl and 2,4,6-trimethyl­phenyl analogues, see: Voliotis et al. (1984 [triangle]). For background literature on kinetic studies, see: Sim et al. (2006 [triangle], 2007 [triangle]).

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Object name is e-64-o1699-scheme1.jpg

Experimental

Crystal data

  • C16H13NO2
  • M r = 251.27
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1699-efi1.jpg
  • a = 15.344 (2) Å
  • b = 7.7731 (8) Å
  • c = 21.693 (2) Å
  • V = 2587.4 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 (2) K
  • 0.15 × 0.10 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 15518 measured reflections
  • 2961 independent reflections
  • 2204 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.104
  • S = 1.01
  • 2961 reflections
  • 172 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020448/tk2280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020448/tk2280Isup2.hkl

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

Acknowledgments

The authors are grateful for a SAGA grant (No. 06-02-03-0147) supporting this study and thank the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

In our studies aimed at understanding the nature of intramolecular general base (IGB) and intramolecular general acid (IGA) catalysis in the hydrolysis of N-substituted phthalimides, we required the preparation of N-phenylphthalimides having a substituent at either the ortho- and/or the para-position. The title compound (I, Fig. 1) is an such an example. In (I), the phthalimido and phenylene portions are flat and are inclined at an angle of 77.2 (1)°.

Experimental

Phthalic anhydride (5.0 g, 33.8 mmol) and o-ethylaniline (4.91 g, 40.5 mmol) were dissolved in glacial acetic acid (15 ml). The mixture was heated at 393–413 K for 4 h; the completion of the reaction was monitored by thin layer chromatography. The mixture was quenched with water. The solid that separated was collected and recrystallized twice from ethanol to give colorless crystals of (I) in 90% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Figures

Fig. 1.
Molecular structure of (I) drawn at the 70% probability level showing atom labelling. Hydrogen atoms are drawn as spheres of arbitrary radiius.

Crystal data

C16H13NO2F000 = 1056
Mr = 251.27Dx = 1.290 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2189 reflections
a = 15.344 (2) Åθ = 2.3–24.0º
b = 7.7731 (8) ŵ = 0.09 mm1
c = 21.693 (2) ÅT = 100 (2) K
V = 2587.4 (5) Å3Irregular block, colourless
Z = 80.15 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer2204 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.3º
ω scansh = −19→11
Absorption correction: nonek = −10→10
15518 measured reflectionsl = −28→28
2961 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.104  w = 1/[σ2(Fo2) + (0.0466P)2 + 0.7719P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2961 reflectionsΔρmax = 0.27 e Å3
172 parametersΔρmin = −0.19 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
O10.48223 (7)0.23894 (15)0.51820 (5)0.0271 (3)
O20.35501 (7)0.02107 (14)0.69268 (5)0.0251 (3)
N10.44007 (8)0.11973 (15)0.61157 (5)0.0171 (3)
C10.42560 (10)0.19354 (18)0.55323 (6)0.0181 (3)
C20.32925 (9)0.20247 (18)0.54575 (6)0.0166 (3)
C30.28005 (10)0.2658 (2)0.49751 (7)0.0204 (3)
H30.30660.31370.46190.024*
C40.18974 (10)0.2565 (2)0.50335 (7)0.0217 (3)
H40.15380.29790.47090.026*
C50.15121 (10)0.1874 (2)0.55597 (7)0.0226 (3)
H50.08950.18190.55860.027*
C60.20135 (10)0.12648 (19)0.60476 (7)0.0203 (3)
H60.17520.08120.64100.024*
C70.29078 (10)0.13462 (18)0.59830 (6)0.0173 (3)
C80.36106 (9)0.08198 (18)0.64160 (7)0.0176 (3)
C90.52461 (9)0.09843 (18)0.63950 (6)0.0162 (3)
C100.57623 (10)−0.03944 (19)0.62150 (7)0.0201 (3)
H100.5564−0.11680.59070.024*
C110.65713 (10)−0.0634 (2)0.64893 (7)0.0221 (3)
H110.6929−0.15720.63680.027*
C120.68547 (10)0.0498 (2)0.69407 (7)0.0222 (3)
H120.74050.03300.71320.027*
C130.63332 (10)0.18808 (19)0.71133 (7)0.0208 (3)
H130.65350.26530.74210.025*
C140.55168 (10)0.21587 (18)0.68431 (6)0.0174 (3)
C150.49902 (10)0.37245 (19)0.70174 (7)0.0215 (3)
H15A0.50720.39700.74620.026*
H15B0.43640.34890.69470.026*
C160.52646 (11)0.5296 (2)0.66405 (8)0.0293 (4)
H16A0.49120.62900.67630.044*
H16B0.51750.50610.62010.044*
H16C0.58820.55420.67160.044*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0171 (6)0.0436 (7)0.0207 (6)−0.0029 (5)0.0029 (5)0.0057 (5)
O20.0185 (6)0.0354 (6)0.0215 (5)−0.0017 (5)−0.0006 (5)0.0095 (5)
N10.0125 (6)0.0226 (6)0.0161 (6)−0.0005 (5)−0.0006 (5)0.0014 (5)
C10.0171 (8)0.0212 (7)0.0160 (7)−0.0012 (6)−0.0001 (6)−0.0013 (6)
C20.0144 (7)0.0177 (7)0.0176 (7)−0.0006 (6)−0.0005 (6)−0.0015 (5)
C30.0192 (8)0.0248 (8)0.0173 (7)0.0003 (6)−0.0008 (6)0.0004 (6)
C40.0195 (8)0.0238 (8)0.0217 (7)0.0036 (6)−0.0062 (6)0.0004 (6)
C50.0117 (7)0.0279 (8)0.0283 (8)0.0010 (6)−0.0013 (6)−0.0007 (7)
C60.0157 (8)0.0238 (8)0.0215 (7)−0.0013 (6)0.0015 (6)0.0021 (6)
C70.0163 (7)0.0173 (7)0.0183 (7)0.0009 (6)−0.0012 (6)0.0001 (6)
C80.0148 (7)0.0191 (7)0.0191 (7)−0.0006 (6)−0.0005 (6)−0.0004 (6)
C90.0106 (7)0.0216 (7)0.0164 (7)−0.0016 (6)0.0002 (6)0.0035 (5)
C100.0193 (8)0.0222 (8)0.0188 (7)−0.0014 (6)−0.0007 (6)−0.0025 (6)
C110.0177 (8)0.0236 (8)0.0251 (8)0.0048 (6)0.0018 (6)0.0001 (6)
C120.0146 (8)0.0265 (8)0.0254 (8)−0.0003 (6)−0.0032 (6)0.0029 (6)
C130.0173 (8)0.0240 (8)0.0211 (7)−0.0041 (6)−0.0029 (6)−0.0009 (6)
C140.0149 (7)0.0195 (7)0.0179 (7)−0.0010 (6)0.0007 (6)0.0013 (6)
C150.0189 (8)0.0221 (8)0.0234 (7)0.0017 (6)−0.0025 (6)−0.0032 (6)
C160.0270 (9)0.0239 (8)0.0369 (9)0.0032 (7)−0.0026 (7)0.0028 (7)

Geometric parameters (Å, °)

O1—C11.2072 (17)C9—C101.389 (2)
O2—C81.2085 (17)C9—C141.397 (2)
N1—C11.4071 (18)C10—C111.389 (2)
N1—C81.4072 (18)C10—H100.9500
N1—C91.4412 (18)C11—C121.387 (2)
C1—C21.489 (2)C11—H110.9500
C2—C31.381 (2)C12—C131.391 (2)
C2—C71.3879 (19)C12—H120.9500
C3—C41.393 (2)C13—C141.400 (2)
C3—H30.9500C13—H130.9500
C4—C51.393 (2)C14—C151.509 (2)
C4—H40.9500C15—C161.529 (2)
C5—C61.392 (2)C15—H15A0.9900
C5—H50.9500C15—H15B0.9900
C6—C71.381 (2)C16—H16A0.9800
C6—H60.9500C16—H16B0.9800
C7—C81.488 (2)C16—H16C0.9800
C1—N1—C8111.43 (12)C14—C9—N1119.02 (13)
C1—N1—C9124.54 (12)C9—C10—C11119.53 (14)
C8—N1—C9123.84 (11)C9—C10—H10120.2
O1—C1—N1124.87 (14)C11—C10—H10120.2
O1—C1—C2129.23 (13)C12—C11—C10119.83 (14)
N1—C1—C2105.90 (12)C12—C11—H11120.1
C3—C2—C7121.70 (14)C10—C11—H11120.1
C3—C2—C1129.94 (13)C11—C12—C13120.01 (14)
C7—C2—C1108.36 (12)C11—C12—H12120.0
C2—C3—C4117.13 (14)C13—C12—H12120.0
C2—C3—H3121.4C12—C13—C14121.41 (14)
C4—C3—H3121.4C12—C13—H13119.3
C5—C4—C3121.11 (14)C14—C13—H13119.3
C5—C4—H4119.4C9—C14—C13117.17 (13)
C3—C4—H4119.4C9—C14—C15122.84 (13)
C4—C5—C6121.31 (14)C13—C14—C15119.91 (13)
C4—C5—H5119.3C14—C15—C16111.27 (13)
C6—C5—H5119.3C14—C15—H15A109.4
C7—C6—C5117.18 (14)C16—C15—H15A109.4
C7—C6—H6121.4C14—C15—H15B109.4
C5—C6—H6121.4C16—C15—H15B109.4
C6—C7—C2121.56 (13)H15A—C15—H15B108.0
C6—C7—C8130.07 (13)C15—C16—H16A109.5
C2—C7—C8108.35 (13)C15—C16—H16B109.5
O2—C8—N1124.92 (13)H16A—C16—H16B109.5
O2—C8—C7129.13 (13)C15—C16—H16C109.5
N1—C8—C7105.95 (12)H16A—C16—H16C109.5
C10—C9—C14122.04 (13)H16B—C16—H16C109.5
C10—C9—N1118.94 (13)
C8—N1—C1—O1179.48 (14)C9—N1—C8—C7175.82 (12)
C9—N1—C1—O14.4 (2)C6—C7—C8—O2−0.6 (3)
C8—N1—C1—C2−0.23 (15)C2—C7—C8—O2178.26 (15)
C9—N1—C1—C2−175.35 (12)C6—C7—C8—N1−179.73 (15)
O1—C1—C2—C3−0.7 (3)C2—C7—C8—N1−0.86 (15)
N1—C1—C2—C3179.03 (14)C1—N1—C9—C10−80.22 (18)
O1—C1—C2—C7179.98 (15)C8—N1—C9—C10105.25 (16)
N1—C1—C2—C7−0.33 (15)C1—N1—C9—C14100.51 (16)
C7—C2—C3—C4−0.9 (2)C8—N1—C9—C14−74.03 (18)
C1—C2—C3—C4179.78 (14)C14—C9—C10—C110.5 (2)
C2—C3—C4—C50.5 (2)N1—C9—C10—C11−178.73 (13)
C3—C4—C5—C60.5 (2)C9—C10—C11—C120.2 (2)
C4—C5—C6—C7−1.1 (2)C10—C11—C12—C13−0.7 (2)
C5—C6—C7—C20.7 (2)C11—C12—C13—C140.4 (2)
C5—C6—C7—C8179.48 (14)C10—C9—C14—C13−0.8 (2)
C3—C2—C7—C60.3 (2)N1—C9—C14—C13178.48 (12)
C1—C2—C7—C6179.72 (13)C10—C9—C14—C15176.18 (13)
C3—C2—C7—C8−178.69 (13)N1—C9—C14—C15−4.6 (2)
C1—C2—C7—C80.73 (15)C12—C13—C14—C90.3 (2)
C1—N1—C8—O2−178.51 (14)C12—C13—C14—C15−176.74 (14)
C9—N1—C8—O2−3.3 (2)C9—C14—C15—C16−92.56 (17)
C1—N1—C8—C70.66 (15)C13—C14—C15—C1684.31 (17)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2280).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bocelli, G. & Cantoni, A. (1989). Acta Cryst. C45, 1658–1660.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Magnomedova, N. S., Dzyabchenko, A. V., Zavodnik, V. E. & Bel’skii, V. K. (1980). Cryst. Struct. Commun.9, 713–715.
  • Shahzadi, S., Ali, S., Najam-ul-Haq, M. & Wurst, K. (2006). Acta Cryst. E62, o2586–o2588.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sim, Y.-L., Ariffin, A. & Khan, M. N. (2006). Int. J. Chem. Kinet.38, 746–758.
  • Sim, Y.-L., Ariffin, A. & Khan, M. N. (2007). J. Org. Chem.72, 2392–2401. [PubMed]
  • Voliotis, S., Arrieta, J. M. & Germain, G. (1984). Acta Cryst. C40, 1946–1948.
  • Westrip, S. P. (2008). publCIF In preparation.

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