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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1699. | PMCID: PMC2960657 |
N-(2-Ethylphenyl)phthalimide Yen May Fan,a Norzalida Zakaria,a Azhar Ariffin,a* and Seik Weng Nga aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia Received July 2, 2008; Accepted July 3, 2008. This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. In the title compound, C16H13NO2, the phthalimide and benzene ring systems form a dihedral angle of 77.2 (1)°. 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 ). Click on image to enlarge
Crystal data
- C16H13NO2
-
M
r = 251.27
- Orthorhombic,
-
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 ); cell refinement: SAINT (Bruker, 2007 ); 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, 2008 ). 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
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). Crystal data C16H13NO2 | F000 = 1056 | Mr = 251.27 | Dx = 1.290 Mg m−3 | Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å | Hall symbol: -P 2ac 2ab | Cell parameters from 2189 reflections | a = 15.344 (2) Å | θ = 2.3–24.0º | b = 7.7731 (8) Å | µ = 0.09 mm−1 | c = 21.693 (2) Å | T = 100 (2) K | V = 2587.4 (5) Å3 | Irregular block, colourless | Z = 8 | 0.15 × 0.10 × 0.05 mm |
Data collection Bruker SMART APEX diffractometer | 2204 reflections with I > 2σ(I) | Radiation source: fine-focus sealed tube | Rint = 0.054 | Monochromator: graphite | θmax = 27.5º | T = 100(2) K | θmin = 2.3º | ω scans | h = −19→11 | Absorption correction: none | k = −10→10 | 15518 measured reflections | l = −28→28 | 2961 independent reflections | |
Refinement Refinement on F2 | Secondary atom site location: difference Fourier map | Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites | R[F2 > 2σ(F2)] = 0.042 | H-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 reflections | Δρmax = 0.27 e Å−3 | 172 parameters | Δρmin = −0.19 e Å−3 | Primary atom site location: structure-invariant direct methods | Extinction correction: none |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) | x | y | z | Uiso*/Ueq | | O1 | 0.48223 (7) | 0.23894 (15) | 0.51820 (5) | 0.0271 (3) | | O2 | 0.35501 (7) | 0.02107 (14) | 0.69268 (5) | 0.0251 (3) | | N1 | 0.44007 (8) | 0.11973 (15) | 0.61157 (5) | 0.0171 (3) | | C1 | 0.42560 (10) | 0.19354 (18) | 0.55323 (6) | 0.0181 (3) | | C2 | 0.32925 (9) | 0.20247 (18) | 0.54575 (6) | 0.0166 (3) | | C3 | 0.28005 (10) | 0.2658 (2) | 0.49751 (7) | 0.0204 (3) | | H3 | 0.3066 | 0.3137 | 0.4619 | 0.024* | | C4 | 0.18974 (10) | 0.2565 (2) | 0.50335 (7) | 0.0217 (3) | | H4 | 0.1538 | 0.2979 | 0.4709 | 0.026* | | C5 | 0.15121 (10) | 0.1874 (2) | 0.55597 (7) | 0.0226 (3) | | H5 | 0.0895 | 0.1819 | 0.5586 | 0.027* | | C6 | 0.20135 (10) | 0.12648 (19) | 0.60476 (7) | 0.0203 (3) | | H6 | 0.1752 | 0.0812 | 0.6410 | 0.024* | | C7 | 0.29078 (10) | 0.13462 (18) | 0.59830 (6) | 0.0173 (3) | | C8 | 0.36106 (9) | 0.08198 (18) | 0.64160 (7) | 0.0176 (3) | | C9 | 0.52461 (9) | 0.09843 (18) | 0.63950 (6) | 0.0162 (3) | | C10 | 0.57623 (10) | −0.03944 (19) | 0.62150 (7) | 0.0201 (3) | | H10 | 0.5564 | −0.1168 | 0.5907 | 0.024* | | C11 | 0.65713 (10) | −0.0634 (2) | 0.64893 (7) | 0.0221 (3) | | H11 | 0.6929 | −0.1572 | 0.6368 | 0.027* | | C12 | 0.68547 (10) | 0.0498 (2) | 0.69407 (7) | 0.0222 (3) | | H12 | 0.7405 | 0.0330 | 0.7132 | 0.027* | | C13 | 0.63332 (10) | 0.18808 (19) | 0.71133 (7) | 0.0208 (3) | | H13 | 0.6535 | 0.2653 | 0.7421 | 0.025* | | C14 | 0.55168 (10) | 0.21587 (18) | 0.68431 (6) | 0.0174 (3) | | C15 | 0.49902 (10) | 0.37245 (19) | 0.70174 (7) | 0.0215 (3) | | H15A | 0.5072 | 0.3970 | 0.7462 | 0.026* | | H15B | 0.4364 | 0.3489 | 0.6947 | 0.026* | | C16 | 0.52646 (11) | 0.5296 (2) | 0.66405 (8) | 0.0293 (4) | | H16A | 0.4912 | 0.6290 | 0.6763 | 0.044* | | H16B | 0.5175 | 0.5061 | 0.6201 | 0.044* | | H16C | 0.5882 | 0.5542 | 0.6716 | 0.044* | |
Atomic displacement parameters (Å2) | U11 | U22 | U33 | U12 | U13 | U23 | O1 | 0.0171 (6) | 0.0436 (7) | 0.0207 (6) | −0.0029 (5) | 0.0029 (5) | 0.0057 (5) | O2 | 0.0185 (6) | 0.0354 (6) | 0.0215 (5) | −0.0017 (5) | −0.0006 (5) | 0.0095 (5) | N1 | 0.0125 (6) | 0.0226 (6) | 0.0161 (6) | −0.0005 (5) | −0.0006 (5) | 0.0014 (5) | C1 | 0.0171 (8) | 0.0212 (7) | 0.0160 (7) | −0.0012 (6) | −0.0001 (6) | −0.0013 (6) | C2 | 0.0144 (7) | 0.0177 (7) | 0.0176 (7) | −0.0006 (6) | −0.0005 (6) | −0.0015 (5) | C3 | 0.0192 (8) | 0.0248 (8) | 0.0173 (7) | 0.0003 (6) | −0.0008 (6) | 0.0004 (6) | C4 | 0.0195 (8) | 0.0238 (8) | 0.0217 (7) | 0.0036 (6) | −0.0062 (6) | 0.0004 (6) | C5 | 0.0117 (7) | 0.0279 (8) | 0.0283 (8) | 0.0010 (6) | −0.0013 (6) | −0.0007 (7) | C6 | 0.0157 (8) | 0.0238 (8) | 0.0215 (7) | −0.0013 (6) | 0.0015 (6) | 0.0021 (6) | C7 | 0.0163 (7) | 0.0173 (7) | 0.0183 (7) | 0.0009 (6) | −0.0012 (6) | 0.0001 (6) | C8 | 0.0148 (7) | 0.0191 (7) | 0.0191 (7) | −0.0006 (6) | −0.0005 (6) | −0.0004 (6) | C9 | 0.0106 (7) | 0.0216 (7) | 0.0164 (7) | −0.0016 (6) | 0.0002 (6) | 0.0035 (5) | C10 | 0.0193 (8) | 0.0222 (8) | 0.0188 (7) | −0.0014 (6) | −0.0007 (6) | −0.0025 (6) | C11 | 0.0177 (8) | 0.0236 (8) | 0.0251 (8) | 0.0048 (6) | 0.0018 (6) | 0.0001 (6) | C12 | 0.0146 (8) | 0.0265 (8) | 0.0254 (8) | −0.0003 (6) | −0.0032 (6) | 0.0029 (6) | C13 | 0.0173 (8) | 0.0240 (8) | 0.0211 (7) | −0.0041 (6) | −0.0029 (6) | −0.0009 (6) | C14 | 0.0149 (7) | 0.0195 (7) | 0.0179 (7) | −0.0010 (6) | 0.0007 (6) | 0.0013 (6) | C15 | 0.0189 (8) | 0.0221 (8) | 0.0234 (7) | 0.0017 (6) | −0.0025 (6) | −0.0032 (6) | C16 | 0.0270 (9) | 0.0239 (8) | 0.0369 (9) | 0.0032 (7) | −0.0026 (7) | 0.0028 (7) |
Geometric parameters (Å, °) O1—C1 | 1.2072 (17) | C9—C10 | 1.389 (2) | O2—C8 | 1.2085 (17) | C9—C14 | 1.397 (2) | N1—C1 | 1.4071 (18) | C10—C11 | 1.389 (2) | N1—C8 | 1.4072 (18) | C10—H10 | 0.9500 | N1—C9 | 1.4412 (18) | C11—C12 | 1.387 (2) | C1—C2 | 1.489 (2) | C11—H11 | 0.9500 | C2—C3 | 1.381 (2) | C12—C13 | 1.391 (2) | C2—C7 | 1.3879 (19) | C12—H12 | 0.9500 | C3—C4 | 1.393 (2) | C13—C14 | 1.400 (2) | C3—H3 | 0.9500 | C13—H13 | 0.9500 | C4—C5 | 1.393 (2) | C14—C15 | 1.509 (2) | C4—H4 | 0.9500 | C15—C16 | 1.529 (2) | C5—C6 | 1.392 (2) | C15—H15A | 0.9900 | C5—H5 | 0.9500 | C15—H15B | 0.9900 | C6—C7 | 1.381 (2) | C16—H16A | 0.9800 | C6—H6 | 0.9500 | C16—H16B | 0.9800 | C7—C8 | 1.488 (2) | C16—H16C | 0.9800 | | | | | C1—N1—C8 | 111.43 (12) | C14—C9—N1 | 119.02 (13) | C1—N1—C9 | 124.54 (12) | C9—C10—C11 | 119.53 (14) | C8—N1—C9 | 123.84 (11) | C9—C10—H10 | 120.2 | O1—C1—N1 | 124.87 (14) | C11—C10—H10 | 120.2 | O1—C1—C2 | 129.23 (13) | C12—C11—C10 | 119.83 (14) | N1—C1—C2 | 105.90 (12) | C12—C11—H11 | 120.1 | C3—C2—C7 | 121.70 (14) | C10—C11—H11 | 120.1 | C3—C2—C1 | 129.94 (13) | C11—C12—C13 | 120.01 (14) | C7—C2—C1 | 108.36 (12) | C11—C12—H12 | 120.0 | C2—C3—C4 | 117.13 (14) | C13—C12—H12 | 120.0 | C2—C3—H3 | 121.4 | C12—C13—C14 | 121.41 (14) | C4—C3—H3 | 121.4 | C12—C13—H13 | 119.3 | C5—C4—C3 | 121.11 (14) | C14—C13—H13 | 119.3 | C5—C4—H4 | 119.4 | C9—C14—C13 | 117.17 (13) | C3—C4—H4 | 119.4 | C9—C14—C15 | 122.84 (13) | C4—C5—C6 | 121.31 (14) | C13—C14—C15 | 119.91 (13) | C4—C5—H5 | 119.3 | C14—C15—C16 | 111.27 (13) | C6—C5—H5 | 119.3 | C14—C15—H15A | 109.4 | C7—C6—C5 | 117.18 (14) | C16—C15—H15A | 109.4 | C7—C6—H6 | 121.4 | C14—C15—H15B | 109.4 | C5—C6—H6 | 121.4 | C16—C15—H15B | 109.4 | C6—C7—C2 | 121.56 (13) | H15A—C15—H15B | 108.0 | C6—C7—C8 | 130.07 (13) | C15—C16—H16A | 109.5 | C2—C7—C8 | 108.35 (13) | C15—C16—H16B | 109.5 | O2—C8—N1 | 124.92 (13) | H16A—C16—H16B | 109.5 | O2—C8—C7 | 129.13 (13) | C15—C16—H16C | 109.5 | N1—C8—C7 | 105.95 (12) | H16A—C16—H16C | 109.5 | C10—C9—C14 | 122.04 (13) | H16B—C16—H16C | 109.5 | C10—C9—N1 | 118.94 (13) | | | | | | | C8—N1—C1—O1 | 179.48 (14) | C9—N1—C8—C7 | 175.82 (12) | C9—N1—C1—O1 | 4.4 (2) | C6—C7—C8—O2 | −0.6 (3) | C8—N1—C1—C2 | −0.23 (15) | C2—C7—C8—O2 | 178.26 (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—C3 | 179.03 (14) | C1—N1—C9—C10 | −80.22 (18) | O1—C1—C2—C7 | 179.98 (15) | C8—N1—C9—C10 | 105.25 (16) | N1—C1—C2—C7 | −0.33 (15) | C1—N1—C9—C14 | 100.51 (16) | C7—C2—C3—C4 | −0.9 (2) | C8—N1—C9—C14 | −74.03 (18) | C1—C2—C3—C4 | 179.78 (14) | C14—C9—C10—C11 | 0.5 (2) | C2—C3—C4—C5 | 0.5 (2) | N1—C9—C10—C11 | −178.73 (13) | C3—C4—C5—C6 | 0.5 (2) | C9—C10—C11—C12 | 0.2 (2) | C4—C5—C6—C7 | −1.1 (2) | C10—C11—C12—C13 | −0.7 (2) | C5—C6—C7—C2 | 0.7 (2) | C11—C12—C13—C14 | 0.4 (2) | C5—C6—C7—C8 | 179.48 (14) | C10—C9—C14—C13 | −0.8 (2) | C3—C2—C7—C6 | 0.3 (2) | N1—C9—C14—C13 | 178.48 (12) | C1—C2—C7—C6 | 179.72 (13) | C10—C9—C14—C15 | 176.18 (13) | C3—C2—C7—C8 | −178.69 (13) | N1—C9—C14—C15 | −4.6 (2) | C1—C2—C7—C8 | 0.73 (15) | C12—C13—C14—C9 | 0.3 (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—C7 | 0.66 (15) | C13—C14—C15—C16 | 84.31 (17) |
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