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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1859.
Published online 2010 June 30. doi:  10.1107/S1600536810024177
PMCID: PMC3006749

N-(2,3,4-Trifluoro­phen­yl)phthalimide

Abstract

In the title compound, C14H6F3NO2, the benzene ring and the phthalimide ring system make a dihedral angle of 60.12 (7)°. Weak inter­molecular C—H(...)O and C—H(...)F hydrogen bonds are present in the crystal structure.

Related literature

The title compound is a key inter­mediate in the synthesis of organic electro-luminescent materials, see: Han & Kay (2005 [triangle]). For the synthesis, see: Valkonen et al. (2007 [triangle]); Barchin et al. (2002 [triangle]). For related structures, see: Xu et al. (2006 [triangle]); Fu et al. (2010 [triangle]).

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Object name is e-66-o1859-scheme1.jpg

Experimental

Crystal data

  • C14H6F3NO2
  • M r = 277.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1859-efi1.jpg
  • a = 6.8422 (14) Å
  • b = 21.082 (4) Å
  • c = 7.9727 (16) Å
  • β = 101.98 (3)°
  • V = 1125.0 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 113 K
  • 0.20 × 0.18 × 0.12 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.972, T max = 0.983
  • 8049 measured reflections
  • 1980 independent reflections
  • 1603 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.094
  • S = 1.03
  • 1980 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024177/ng2787sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024177/ng2787Isup2.hkl

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

Acknowledgments

The work was supported by the Major Research Program of Zhejiang Province (No. 2008 C02007–2) and the Zhejiang Provincial Natural Science Foundation of China (No. Y307128).

supplementary crystallographic information

Comment

The title compound is a key intermediate in the synthesis of organic electro-luminescent materials. The emission of light by organic molecules exposed to an electric field has been wide investigated in both an academic and industrial context. (Han & Kay, 2005).

The molecular structure of the title compound is illustrated in Fig. 1. In the title compound, two rings are nearly planar, but the molecule as a whole is not planar. The dihedral angle between the benzene ring and the phthalimide plane is 60.12 (7) °, which is similar to 59.95 (4) ° found in a related compound N-(2-fluorophenyl)phthalimide (Xu et al. 2006). Weak intermolecular C—H···O and C—H···F hydrogen bonding are present in the crystal structure (Table 1).

Experimental

An acetic acid solution of phthalic anhydride (14.8 g, 100 mmol) and 2,3,4-trifluoroaniline (10.55 ml, 100 mmol) was refluxed overnight, and then filtered. The crude product was recrystallized from ethyl acetate.

Refinement

H atoms were positioned geometrically and refined as riding with C—H = 0.95 Å, and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
View of the molecule of showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C14H6F3NO2F(000) = 560
Mr = 277.20Dx = 1.637 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3644 reflections
a = 6.8422 (14) Åθ = 1.9–27.8°
b = 21.082 (4) ŵ = 0.14 mm1
c = 7.9727 (16) ÅT = 113 K
β = 101.98 (3)°Prism, colorless
V = 1125.0 (4) Å30.20 × 0.18 × 0.12 mm
Z = 4

Data collection

Rigaku Saturn CCD area-detector diffractometer1980 independent reflections
Radiation source: rotating anode1603 reflections with I > 2σ(I)
confocalRint = 0.034
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 1.9°
ω and [var phi] scansh = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −24→25
Tmin = 0.972, Tmax = 0.983l = −7→9
8049 measured 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)] = 0.034H-atom parameters constrained
wR(F2) = 0.094w = 1/[σ2(Fo2) + (0.0663P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
1980 reflectionsΔρmax = 0.34 e Å3
182 parametersΔρmin = −0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.097 (6)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
F10.36805 (13)0.27803 (5)1.30697 (12)0.0324 (3)
F20.04277 (12)0.20200 (5)1.25161 (11)0.0286 (3)
F30.00346 (11)0.10870 (4)1.01757 (10)0.0245 (3)
O10.29321 (15)0.14544 (5)0.58108 (12)0.0246 (3)
O20.28164 (15)0.00092 (5)1.01024 (12)0.0228 (3)
N10.28999 (17)0.08556 (6)0.82561 (14)0.0181 (3)
C10.28328 (19)0.09456 (7)0.64828 (17)0.0176 (3)
C20.26306 (18)0.02990 (7)0.57338 (17)0.0162 (3)
C30.2489 (2)0.01067 (7)0.40531 (18)0.0193 (4)
H30.24750.04060.31600.023*
C40.23668 (19)−0.05431 (8)0.37222 (18)0.0214 (4)
H40.2272−0.06900.25820.026*
C50.2381 (2)−0.09816 (8)0.50331 (18)0.0231 (4)
H50.2302−0.14220.47710.028*
C60.2507 (2)−0.07859 (7)0.67177 (18)0.0200 (3)
H60.2510−0.10830.76130.024*
C70.26293 (18)−0.01410 (7)0.70366 (16)0.0161 (3)
C80.27847 (19)0.02073 (7)0.86743 (17)0.0168 (3)
C90.31396 (19)0.13524 (7)0.94859 (17)0.0175 (3)
C100.4794 (2)0.17526 (7)0.97522 (18)0.0216 (4)
H100.57960.16930.91020.026*
C110.4998 (2)0.22367 (8)1.09549 (19)0.0240 (4)
H110.61250.25101.11290.029*
C120.3538 (2)0.23125 (7)1.18896 (18)0.0225 (4)
C130.1879 (2)0.19236 (8)1.16429 (18)0.0207 (4)
C140.16934 (19)0.14500 (7)1.04425 (17)0.0181 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0371 (5)0.0252 (6)0.0336 (5)−0.0042 (4)0.0044 (4)−0.0152 (4)
F20.0289 (5)0.0319 (6)0.0280 (5)0.0003 (4)0.0132 (4)−0.0096 (4)
F30.0213 (5)0.0273 (6)0.0262 (5)−0.0077 (4)0.0080 (3)−0.0059 (4)
O10.0342 (6)0.0189 (7)0.0220 (6)0.0039 (5)0.0086 (4)0.0058 (4)
O20.0300 (6)0.0236 (7)0.0159 (5)−0.0026 (4)0.0072 (4)0.0024 (4)
N10.0239 (6)0.0158 (7)0.0156 (6)−0.0014 (5)0.0062 (5)−0.0003 (5)
C10.0159 (7)0.0224 (9)0.0150 (7)0.0029 (6)0.0044 (6)0.0032 (6)
C20.0126 (6)0.0191 (9)0.0172 (7)0.0018 (6)0.0039 (5)0.0014 (6)
C30.0164 (7)0.0271 (10)0.0145 (7)0.0022 (6)0.0030 (5)0.0015 (6)
C40.0175 (7)0.0288 (10)0.0177 (7)0.0014 (6)0.0029 (6)−0.0041 (6)
C50.0228 (8)0.0215 (9)0.0253 (8)−0.0002 (6)0.0053 (6)−0.0065 (6)
C60.0210 (7)0.0184 (9)0.0209 (8)0.0001 (6)0.0047 (6)0.0006 (6)
C70.0139 (7)0.0190 (9)0.0157 (7)0.0007 (6)0.0035 (5)−0.0001 (5)
C80.0157 (7)0.0179 (9)0.0176 (7)0.0003 (6)0.0051 (5)0.0010 (6)
C90.0216 (7)0.0165 (9)0.0141 (7)0.0006 (6)0.0027 (6)0.0007 (6)
C100.0222 (7)0.0198 (9)0.0242 (8)−0.0010 (6)0.0076 (6)0.0027 (6)
C110.0229 (8)0.0199 (9)0.0280 (8)−0.0045 (6)0.0025 (6)0.0012 (6)
C120.0285 (8)0.0165 (9)0.0200 (7)0.0011 (6)−0.0003 (6)−0.0041 (6)
C130.0215 (7)0.0233 (9)0.0181 (7)0.0027 (6)0.0058 (6)0.0008 (6)
C140.0172 (7)0.0180 (9)0.0179 (7)−0.0029 (6)0.0011 (6)0.0005 (6)

Geometric parameters (Å, °)

F1—C121.3525 (17)C4—H40.9500
F2—C131.3411 (17)C5—C61.390 (2)
F3—C141.3486 (16)C5—H50.9500
O1—C11.2072 (18)C6—C71.382 (2)
O2—C81.2087 (16)C6—H60.9500
N1—C81.4129 (19)C7—C81.4824 (19)
N1—C11.4178 (17)C9—C141.384 (2)
N1—C91.4207 (18)C9—C101.392 (2)
C1—C21.483 (2)C10—C111.387 (2)
C2—C31.3840 (19)C10—H100.9500
C2—C71.3927 (19)C11—C121.374 (2)
C3—C41.394 (2)C11—H110.9500
C3—H30.9500C12—C131.381 (2)
C4—C51.394 (2)C13—C141.371 (2)
C8—N1—C1111.90 (11)C2—C7—C8108.41 (13)
C8—N1—C9123.66 (11)O2—C8—N1124.44 (13)
C1—N1—C9124.39 (12)O2—C8—C7129.98 (14)
O1—C1—N1124.63 (13)N1—C8—C7105.58 (11)
O1—C1—C2130.33 (13)C14—C9—C10118.52 (13)
N1—C1—C2105.04 (12)C14—C9—N1119.76 (12)
C3—C2—C7121.07 (14)C10—C9—N1121.72 (12)
C3—C2—C1129.87 (13)C11—C10—C9120.87 (13)
C7—C2—C1109.05 (12)C11—C10—H10119.6
C2—C3—C4117.42 (13)C9—C10—H10119.6
C2—C3—H3121.3C12—C11—C10118.70 (14)
C4—C3—H3121.3C12—C11—H11120.7
C5—C4—C3121.26 (14)C10—C11—H11120.7
C5—C4—H4119.4F1—C12—C11120.43 (13)
C3—C4—H4119.4F1—C12—C13118.06 (13)
C6—C5—C4121.12 (15)C11—C12—C13121.50 (14)
C6—C5—H5119.5F2—C13—C14120.11 (13)
C4—C5—H5119.5F2—C13—C12120.76 (13)
C7—C6—C5117.30 (14)C14—C13—C12119.08 (13)
C7—C6—H6121.3F3—C14—C13118.45 (12)
C5—C6—H6121.3F3—C14—C9120.21 (12)
C6—C7—C2121.82 (13)C13—C14—C9121.32 (13)
C6—C7—C8129.77 (13)
C8—N1—C1—O1−179.01 (13)C2—C7—C8—O2179.32 (13)
C9—N1—C1—O1−1.5 (2)C6—C7—C8—N1178.93 (13)
C8—N1—C1—C20.83 (14)C2—C7—C8—N1−0.75 (14)
C9—N1—C1—C2178.32 (11)C8—N1—C9—C14−61.69 (18)
O1—C1—C2—C3−0.5 (2)C1—N1—C9—C14121.12 (15)
N1—C1—C2—C3179.72 (13)C8—N1—C9—C10118.90 (15)
O1—C1—C2—C7178.52 (14)C1—N1—C9—C10−58.29 (18)
N1—C1—C2—C7−1.30 (14)C14—C9—C10—C110.3 (2)
C7—C2—C3—C4−0.67 (19)N1—C9—C10—C11179.76 (13)
C1—C2—C3—C4178.21 (12)C9—C10—C11—C120.3 (2)
C2—C3—C4—C50.2 (2)C10—C11—C12—F1−179.77 (13)
C3—C4—C5—C60.3 (2)C10—C11—C12—C13−0.7 (2)
C4—C5—C6—C7−0.34 (19)F1—C12—C13—F21.9 (2)
C5—C6—C7—C2−0.13 (19)C11—C12—C13—F2−177.27 (13)
C5—C6—C7—C8−179.77 (13)F1—C12—C13—C14179.41 (13)
C3—C2—C7—C60.7 (2)C11—C12—C13—C140.3 (2)
C1—C2—C7—C6−178.43 (12)F2—C13—C14—F3−0.3 (2)
C3—C2—C7—C8−179.64 (11)C12—C13—C14—F3−177.88 (12)
C1—C2—C7—C81.28 (14)F2—C13—C14—C9178.01 (12)
C1—N1—C8—O2179.85 (12)C12—C13—C14—C90.4 (2)
C9—N1—C8—O22.3 (2)C10—C9—C14—F3177.54 (12)
C1—N1—C8—C7−0.09 (14)N1—C9—C14—F3−1.9 (2)
C9—N1—C8—C7−177.60 (11)C10—C9—C14—C13−0.7 (2)
C6—C7—C8—O2−1.0 (2)N1—C9—C14—C13179.83 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.952.553.1855 (18)124
C10—H10···F1ii0.952.543.3647 (18)145
C11—H11···O1iii0.952.553.428 (2)154

Symmetry codes: (i) x, y, z−1; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2787).

References

  • Barchin, B. M., Cuadro, A. M. & Alvarez-Builla, J. (2002). Synlett, 2, 343–345.
  • Fu, X.-S., Yu, X.-P., Wang, W.-M. & Lin, F. (2010). Acta Cryst. E66, o1744. [PMC free article] [PubMed]
  • Han, K. J. & Kay, K. Y. (2005). J. Korean Chem. Soc.49, 233–238.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Valkonen, A., Lahtinen, T. & Rissanen, K. (2007). Acta Cryst. E63, o472–o473.
  • Xu, D., Shi, Y.-Q., Chen, B., Cheng, Y.-H. & Gao, X. (2006). Acta Cryst. E62, o408–o409.

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