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

Fu, X.-S.; Yu, X.-P.; Wang, W.-M.; Lin, F.

doi:10.1107/S1600536810023032

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1744

doi:10.1107/S1600536810023032

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

Xian-Shu Fu,^a Xiao-Ping Yu,^a Wei-Min Wang ^a ^* and Fang Lin ^a

^aCollege of Life Sciences, China Jiliang University, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: clshangzhou@yahoo.com.cn

(Received 7 June 2010; accepted 15 June 2010; online 23 June 2010)

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 ). For a related structure, see: Xu et al. (2006 ).

Experimental

Crystal data

C₁₄H₄Cl₄FNO₂
M_r = 378.98
Orthorhombic, P c c a
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 ) 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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.204
S = 1.04
1174 reflections
103 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cl2ⁱ	0.95	2.80	3.690 (4)	157
Symmetry code: (i) $[-x, y+1, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

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

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023032/xu2780Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear (Rigaku/MSC, 2001); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

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

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

Crystal data top

C₁₄H₄Cl₄FNO₂	F(000) = 752
M_r = 378.98	D_x = 1.896 Mg m⁻³
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 3007 reflections
a = 7.9400 (16) Å	θ = 2.8–27.9°
b = 5.6744 (11) Å	µ = 0.91 mm⁻¹
c = 29.461 (6) Å	T = 113 K
V = 1327.4 (5) Å³	Prism, colorless
Z = 4	0.20 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1174 independent reflections
Radiation source: rotating anode	1053 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.039
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.8°
ω and ϕ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	k = −6→6
T_min = 0.839, T_max = 0.899	l = −35→30
6423 measured reflections

Refinement top

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.204	w = 1/[σ²(F_o²) + (0.1623P)² + 2.0637P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
1174 reflections	Δρ_max = 0.84 e Å⁻³
103 parameters	Δρ_min = −0.74 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (8)

Crystal data top

C₁₄H₄Cl₄FNO₂	V = 1327.4 (5) Å³
M_r = 378.98	Z = 4
Orthorhombic, Pcca	Mo Kα radiation
a = 7.9400 (16) Å	µ = 0.91 mm⁻¹
b = 5.6744 (11) Å	T = 113 K
c = 29.461 (6) Å	0.20 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1174 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	1053 reflections with I > 2σ(I)
T_min = 0.839, T_max = 0.899	R_int = 0.039
6423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.204	H-atom parameters constrained
S = 1.04	Δρ_max = 0.84 e Å⁻³
1174 reflections	Δρ_min = −0.74 e Å⁻³
103 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Cl1	0.14081 (12)	0.27246 (16)	−0.00242 (3)	0.0266 (5)
Cl2	0.01306 (11)	0.05859 (15)	0.08874 (3)	0.0246 (5)
F1	0.2500	0.5000	0.39104 (10)	0.0445 (10)
O1	0.0906 (3)	0.1621 (5)	0.19160 (8)	0.0236 (7)
N1	0.2500	0.5000	0.20376 (13)	0.0224 (10)
C1	0.1999 (4)	0.4011 (6)	0.04757 (10)	0.0199 (8)
C2	0.1431 (4)	0.3007 (7)	0.08894 (12)	0.0209 (9)
C3	0.1986 (4)	0.4021 (6)	0.12895 (12)	0.0184 (8)
C4	0.1677 (4)	0.3289 (6)	0.17733 (11)	0.0183 (8)
C5	0.2500	0.5000	0.25202 (14)	0.0173 (11)
C6	0.1893 (4)	0.6957 (6)	0.27533 (11)	0.0206 (8)
H6	0.1499	0.8293	0.2591	0.025*
C7	0.1864 (5)	0.6948 (7)	0.32247 (12)	0.0264 (9)
H7	0.1419	0.8248	0.3389	0.032*
C8	0.2500	0.5000	0.34501 (17)	0.0338 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0358 (8)	0.0274 (8)	0.0165 (7)	0.0042 (4)	−0.0031 (3)	−0.0059 (3)
Cl2	0.0301 (7)	0.0219 (8)	0.0219 (7)	−0.0043 (3)	−0.0010 (3)	−0.0042 (3)
F1	0.063 (2)	0.054 (2)	0.0166 (17)	−0.027 (2)	0.000	0.000
O1	0.0269 (14)	0.0221 (14)	0.0218 (13)	−0.0051 (10)	0.0023 (10)	0.0039 (10)
N1	0.032 (2)	0.017 (2)	0.017 (2)	−0.0042 (18)	0.000	0.000
C1	0.0228 (18)	0.0250 (18)	0.0119 (17)	0.0079 (13)	−0.0016 (11)	−0.0046 (12)
C2	0.0182 (16)	0.0226 (19)	0.022 (2)	0.0011 (13)	0.0021 (11)	0.0000 (14)
C3	0.0179 (16)	0.0204 (16)	0.0168 (17)	0.0031 (13)	−0.0014 (12)	−0.0001 (13)
C4	0.0159 (14)	0.0220 (19)	0.0171 (18)	0.0024 (14)	−0.0009 (12)	0.0013 (13)
C5	0.014 (2)	0.020 (2)	0.018 (2)	−0.0002 (18)	0.000	0.000
C6	0.0195 (16)	0.0208 (18)	0.0213 (18)	−0.0038 (13)	0.0008 (12)	−0.0016 (14)
C7	0.0243 (18)	0.030 (2)	0.0252 (19)	−0.0066 (15)	0.0024 (14)	−0.0089 (15)
C8	0.050 (3)	0.036 (3)	0.015 (2)	−0.025 (3)	0.000	0.000

Geometric parameters (Å, º) top

Cl1—C1	1.709 (3)	C3—C3ⁱ	1.379 (7)
Cl2—C2	1.719 (4)	C3—C4	1.504 (5)
F1—C8	1.356 (6)	C5—C6	1.392 (4)
O1—C4	1.203 (5)	C5—C6ⁱ	1.392 (4)
N1—C4	1.406 (4)	C6—C7	1.389 (5)
N1—C4ⁱ	1.406 (4)	C6—H6	0.9500
N1—C5	1.422 (5)	C7—C8	1.385 (5)
C1—C1ⁱ	1.376 (7)	C7—H7	0.9500
C1—C2	1.419 (5)	C8—C7ⁱ	1.385 (5)
C2—C3	1.384 (5)

C4—N1—C4ⁱ	112.7 (4)	N1—C4—C3	105.0 (3)
C4—N1—C5	123.7 (2)	C6—C5—C6ⁱ	120.9 (4)
C4ⁱ—N1—C5	123.7 (2)	C6—C5—N1	119.6 (2)
C1ⁱ—C1—C2	120.7 (2)	C6ⁱ—C5—N1	119.6 (2)
C1ⁱ—C1—Cl1	120.48 (13)	C7—C6—C5	119.7 (3)
C2—C1—Cl1	118.8 (3)	C7—C6—H6	120.1
C3—C2—C1	117.6 (3)	C5—C6—H6	120.1
C3—C2—Cl2	121.8 (3)	C8—C7—C6	118.4 (4)
C1—C2—Cl2	120.6 (3)	C8—C7—H7	120.8
C3ⁱ—C3—C2	121.6 (2)	C6—C7—H7	120.8
C3ⁱ—C3—C4	108.58 (19)	F1—C8—C7ⁱ	118.6 (2)
C2—C3—C4	129.8 (3)	F1—C8—C7	118.6 (2)
O1—C4—N1	125.9 (3)	C7ⁱ—C8—C7	122.7 (5)
O1—C4—C3	129.1 (3)

C1ⁱ—C1—C2—C3	−3.0 (6)	C2—C3—C4—O1	1.9 (6)
Cl1—C1—C2—C3	177.3 (2)	C3ⁱ—C3—C4—N1	3.1 (4)
C1ⁱ—C1—C2—Cl2	178.1 (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—C3ⁱ	1.9 (6)	C4ⁱ—N1—C5—C6	57.4 (2)
Cl2—C2—C3—C3ⁱ	−179.2 (3)	C4—N1—C5—C6ⁱ	57.4 (2)
C1—C2—C3—C4	−176.6 (3)	C4ⁱ—N1—C5—C6ⁱ	−122.6 (2)
Cl2—C2—C3—C4	2.3 (5)	C6ⁱ—C5—C6—C7	−1.1 (2)
C4ⁱ—N1—C4—O1	178.8 (4)	N1—C5—C6—C7	178.9 (2)
C5—N1—C4—O1	−1.2 (4)	C5—C6—C7—C8	2.1 (4)
C4ⁱ—N1—C4—C3	−1.12 (15)	C6—C7—C8—F1	178.9 (2)
C5—N1—C4—C3	178.88 (15)	C6—C7—C8—C7ⁱ	−1.1 (2)
C3ⁱ—C3—C4—O1	−176.8 (4)

Symmetry code: (i) −x+1/2, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl2ⁱⁱ	0.95	2.80	3.690 (4)	157

Symmetry code: (ii) −x, y+1, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₄Cl₄FNO₂
M_r	378.98
Crystal system, space group	Orthorhombic, Pcca
Temperature (K)	113
a, b, c (Å)	7.9400 (16), 5.6744 (11), 29.461 (6)
V (Å³)	1327.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2001)
T_min, T_max	0.839, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	6423, 1174, 1053
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.204, 1.04
No. of reflections	1174
No. of parameters	103
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.74

Computer programs: CrystalClear (Rigaku/MSC, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl2ⁱ	0.95	2.80	3.690 (4)	157

Symmetry code: (i) −x, y+1, −z+1/2.

Acknowledgements

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).

References

Han, K. J. & Kay, K. Y. (2005). J. Korean Chem. Soc. 49, 233–238. CAS Google Scholar
Rigaku/MSC (2001). CrystalClear. Rigaku/MSC, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, D., Shi, Y.-Q., Chen, B., Cheng, Y.-H. & Gao, X. (2006). Acta Cryst. E62, o408–o409. Web of Science CSD CrossRef IUCr Journals Google Scholar