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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1744.
Published online 2010 June 23. doi:  10.1107/S1600536810023032
PMCID: PMC3006924

4,5,6,7-Tetra­chloro-2-(4-fluoro­phen­yl)isoindoline-1,3-dione

Abstract

The title compound, C14H4Cl4FNO2, has crystallographic twofold symmetry with the N and F atoms and two C atoms of the benzene ring located on a twofold rotation axis. The isoindole­dione ring system is almost planar [maximum atomic deviation = 0.036 (3) Å], and is twisted with respect to the florobenzene ring, making a dihedral angle of 58.56 (16)°. Weak inter­molecular C—H(...)Cl hydrogen bonding is present in the crystal structure.

Related literature

The title compound is an inter­mediate in the synthesis of organic electro-luminescent materials, see: Han & Kay (2005 [triangle]). For a related structure, see: Xu et al. (2006 [triangle]).

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Object name is e-66-o1744-scheme1.jpg

Experimental

Crystal data

  • C14H4Cl4FNO2
  • M r = 378.98
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1744-efi1.jpg
  • a = 7.9400 (16) Å
  • b = 5.6744 (11) Å
  • c = 29.461 (6) Å
  • V = 1327.4 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.91 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/MSC, 2001 [triangle]) T min = 0.839, T max = 0.899
  • 6423 measured reflections
  • 1174 independent reflections
  • 1053 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.204
  • S = 1.04
  • 1174 reflections
  • 103 parameters
  • H-atom parameters constrained
  • Δρmax = 0.84 e Å−3
  • Δρmin = −0.74 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 [triangle]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 [triangle]); 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023032/xu2780sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023032/xu2780Isup2.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, the dihedral angle between the benzene ring and the indole ring system is 58.56 (16)°, which is similar to 59.95 (4)° found in a related compound N-(2-fluorophenyl)phthalimide (Xu et al., 2006). Weak intermolecular C—H···Cl hydrogen bonding is present in the crystal structure (Table 1).

Experimental

An acetic acid solution of tetrachlorophthalic anhydride (28.6 g, 100 mmol) and 4-fluoroaniline (9.45 ml, 100 mmol) was refluxed overnight, and then filtered. The crude produce 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

C14H4Cl4FNO2F(000) = 752
Mr = 378.98Dx = 1.896 Mg m3
Orthorhombic, PccaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2acCell parameters from 3007 reflections
a = 7.9400 (16) Åθ = 2.8–27.9°
b = 5.6744 (11) ŵ = 0.91 mm1
c = 29.461 (6) ÅT = 113 K
V = 1327.4 (5) Å3Prism, colorless
Z = 40.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer1174 independent reflections
Radiation source: rotating anode1053 reflections with I > 2σ(I)
confocalRint = 0.039
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.8°
ω and [var phi] scansh = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)k = −6→6
Tmin = 0.839, Tmax = 0.899l = −35→30
6423 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)] = 0.050H-atom parameters constrained
wR(F2) = 0.204w = 1/[σ2(Fo2) + (0.1623P)2 + 2.0637P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
1174 reflectionsΔρmax = 0.84 e Å3
103 parametersΔρmin = −0.74 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: 0.039 (8)

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
Cl10.14081 (12)0.27246 (16)−0.00242 (3)0.0266 (5)
Cl20.01306 (11)0.05859 (15)0.08874 (3)0.0246 (5)
F10.25000.50000.39104 (10)0.0445 (10)
O10.0906 (3)0.1621 (5)0.19160 (8)0.0236 (7)
N10.25000.50000.20376 (13)0.0224 (10)
C10.1999 (4)0.4011 (6)0.04757 (10)0.0199 (8)
C20.1431 (4)0.3007 (7)0.08894 (12)0.0209 (9)
C30.1986 (4)0.4021 (6)0.12895 (12)0.0184 (8)
C40.1677 (4)0.3289 (6)0.17733 (11)0.0183 (8)
C50.25000.50000.25202 (14)0.0173 (11)
C60.1893 (4)0.6957 (6)0.27533 (11)0.0206 (8)
H60.14990.82930.25910.025*
C70.1864 (5)0.6948 (7)0.32247 (12)0.0264 (9)
H70.14190.82480.33890.032*
C80.25000.50000.34501 (17)0.0338 (14)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0358 (8)0.0274 (8)0.0165 (7)0.0042 (4)−0.0031 (3)−0.0059 (3)
Cl20.0301 (7)0.0219 (8)0.0219 (7)−0.0043 (3)−0.0010 (3)−0.0042 (3)
F10.063 (2)0.054 (2)0.0166 (17)−0.027 (2)0.0000.000
O10.0269 (14)0.0221 (14)0.0218 (13)−0.0051 (10)0.0023 (10)0.0039 (10)
N10.032 (2)0.017 (2)0.017 (2)−0.0042 (18)0.0000.000
C10.0228 (18)0.0250 (18)0.0119 (17)0.0079 (13)−0.0016 (11)−0.0046 (12)
C20.0182 (16)0.0226 (19)0.022 (2)0.0011 (13)0.0021 (11)0.0000 (14)
C30.0179 (16)0.0204 (16)0.0168 (17)0.0031 (13)−0.0014 (12)−0.0001 (13)
C40.0159 (14)0.0220 (19)0.0171 (18)0.0024 (14)−0.0009 (12)0.0013 (13)
C50.014 (2)0.020 (2)0.018 (2)−0.0002 (18)0.0000.000
C60.0195 (16)0.0208 (18)0.0213 (18)−0.0038 (13)0.0008 (12)−0.0016 (14)
C70.0243 (18)0.030 (2)0.0252 (19)−0.0066 (15)0.0024 (14)−0.0089 (15)
C80.050 (3)0.036 (3)0.015 (2)−0.025 (3)0.0000.000

Geometric parameters (Å, °)

Cl1—C11.709 (3)C3—C3i1.379 (7)
Cl2—C21.719 (4)C3—C41.504 (5)
F1—C81.356 (6)C5—C61.392 (4)
O1—C41.203 (5)C5—C6i1.392 (4)
N1—C41.406 (4)C6—C71.389 (5)
N1—C4i1.406 (4)C6—H60.9500
N1—C51.422 (5)C7—C81.385 (5)
C1—C1i1.376 (7)C7—H70.9500
C1—C21.419 (5)C8—C7i1.385 (5)
C2—C31.384 (5)
C4—N1—C4i112.7 (4)N1—C4—C3105.0 (3)
C4—N1—C5123.7 (2)C6—C5—C6i120.9 (4)
C4i—N1—C5123.7 (2)C6—C5—N1119.6 (2)
C1i—C1—C2120.7 (2)C6i—C5—N1119.6 (2)
C1i—C1—Cl1120.48 (13)C7—C6—C5119.7 (3)
C2—C1—Cl1118.8 (3)C7—C6—H6120.1
C3—C2—C1117.6 (3)C5—C6—H6120.1
C3—C2—Cl2121.8 (3)C8—C7—C6118.4 (4)
C1—C2—Cl2120.6 (3)C8—C7—H7120.8
C3i—C3—C2121.6 (2)C6—C7—H7120.8
C3i—C3—C4108.58 (19)F1—C8—C7i118.6 (2)
C2—C3—C4129.8 (3)F1—C8—C7118.6 (2)
O1—C4—N1125.9 (3)C7i—C8—C7122.7 (5)
O1—C4—C3129.1 (3)
C1i—C1—C2—C3−3.0 (6)C2—C3—C4—O11.9 (6)
Cl1—C1—C2—C3177.3 (2)C3i—C3—C4—N13.1 (4)
C1i—C1—C2—Cl2178.1 (3)C2—C3—C4—N1−178.2 (3)
Cl1—C1—C2—Cl2−1.6 (4)C4—N1—C5—C6−122.6 (2)
C1—C2—C3—C3i1.9 (6)C4i—N1—C5—C657.4 (2)
Cl2—C2—C3—C3i−179.2 (3)C4—N1—C5—C6i57.4 (2)
C1—C2—C3—C4−176.6 (3)C4i—N1—C5—C6i−122.6 (2)
Cl2—C2—C3—C42.3 (5)C6i—C5—C6—C7−1.1 (2)
C4i—N1—C4—O1178.8 (4)N1—C5—C6—C7178.9 (2)
C5—N1—C4—O1−1.2 (4)C5—C6—C7—C82.1 (4)
C4i—N1—C4—C3−1.12 (15)C6—C7—C8—F1178.9 (2)
C5—N1—C4—C3178.88 (15)C6—C7—C8—C7i−1.1 (2)
C3i—C3—C4—O1−176.8 (4)

Symmetry codes: (i) −x+1/2, −y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···Cl2ii0.952.803.690 (4)157

Symmetry codes: (ii) −x, y+1, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2780).

References

  • Han, K. J. & Kay, K. Y. (2005). J. Korean Chem. Soc.49, 233–238.
  • Rigaku/MSC (2001). CrystalClear Rigaku/MSC, Tokyo, Japan.
  • Rigaku/MSC (2004). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xu, D., Shi, Y.-Q., Chen, B., Cheng, Y.-H. & Gao, X. (2006). Acta Cryst. E62, o408–o409.

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