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Acta Cryst. (2008). E64, o1699    [ doi:10.1107/S1600536808020448 ]

N-(2-Ethylphenyl)phthalimide

Y. M. Fan, N. Zakaria, A. Ariffin and S. W. Ng

Abstract top

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

Comment top

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)°.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) drawn at the 70% probability level showing atom labelling. Hydrogen atoms are drawn as spheres of arbitrary radiius.
N-(2-Ethylphenyl)phthalimide top
Crystal data top
C16H13NO2F000 = 1056
Mr = 251.27Dx = 1.290 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		2204 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 top
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 Å−3
172 parametersΔρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C16H13NO2V = 2587.4 (5) Å3
Mr = 251.27Z = 8
Orthorhombic, PbcaMo Kα
a = 15.344 (2) ŵ = 0.09 mm−1
b = 7.7731 (8) ÅT = 100 (2) K
c = 21.693 (2) Å0.15 × 0.10 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		2961 independent reflections
Absorption correction: none2204 reflections with I > 2σ(I)
15518 measured reflectionsRint = 0.054
Refinement top
R[F2 > 2σ(F2)] = 0.042172 parameters
wR(F2) = 0.104H-atom parameters constrained
S = 1.01Δρmax = 0.27 e Å−3
2961 reflectionsΔρmin = −0.19 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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)
Acknowledgements top

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.

references
References top

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Westrip, S. P. (2008). publCIF. In preparation.