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

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

doi:10.1107/S1600536810023019

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1743

doi:10.1107/S1600536810023019

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4,5,6,7-Tetrachloro-2-(2,2,2-trifluoroethyl)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)

In the title compound, C₁₀H₂Cl₄F₃NO₂, the isoindoline ring system is almostplanar, the maximum atomic deviation being 0.064 (2) Å. The C—C bond of the ethylene group is twisted with respect to the isoindoline plane by a dihedral angle of 59.58 (12)°. In the crystal, weak intermolecular C—H⋯F hydrogen bonding links the molecules into supramolecular chains running along the a axis. A short intermolecular Cl⋯O contact of 2.950 (3) Å is also observed.

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: Valkonen et al. (2007 ).

Experimental

Crystal data

C₁₀H₂Cl₄F₃NO₂
M_r = 366.93
Triclinic, $[P \overline 1]$
a = 4.943 (4) Å
b = 10.759 (9) Å
c = 12.130 (11) Å
α = 101.373 (19)°
β = 101.18 (2)°
γ = 92.704 (3)°
V = 617.9 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 113 K
0.20 × 0.08 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001 ) T_min = 0.826, T_max = 0.943
5139 measured reflections
2126 independent reflections
2033 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.078
S = 1.07
2126 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯F1ⁱ	0.99	2.38	3.289 (4)	152
Symmetry code: (i) x-1, y, z.

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/S1600536810023019/xu2778sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023019/xu2778Isup2.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. The isoindole ring system is planar, the maximum atomic deviation being 0.064 (2)Å (for C8 atom). The C9—C10 bond of the ethylene group is twisted with respect to the isoindole ring by a dihedral angle of 59.58 (12)°, which is similar to 60.3 (5)° found in a related compound 2-(2-iodoethyl)isoindole-1,3-dione (Valkonen et al. 2007). Weak intermolecular C—H···F 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: Valkonen et al. (2007).

Experimental top

An acetic acid solution of tetrachlorophthalic anhydride (28.6 g, 100 mmol) and 2,2,2-trifluoroethylamine (7.99 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-(2,2,2-trifluoroethyl)isoindoline-1,3-dione top

Crystal data top

C₁₀H₂Cl₄F₃NO₂	Z = 2
M_r = 366.93	F(000) = 360
Triclinic, P1	D_x = 1.972 Mg m⁻³
Hall symbol: -P 1	Melting point: 477 K
a = 4.943 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.759 (9) Å	Cell parameters from 2510 reflections
c = 12.130 (11) Å	θ = 1.8–27.9°
α = 101.373 (19)°	µ = 0.99 mm⁻¹
β = 101.18 (2)°	T = 113 K
γ = 92.704 (3)°	Prism, colorless
V = 617.9 (9) Å³	0.20 × 0.08 × 0.06 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2126 independent reflections
Radiation source: fine-focus sealed tube	2033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 14.63 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
ω and ϕ scans	h = −5→5
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	k = −12→12
T_min = 0.826, T_max = 0.943	l = −14→11
5139 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0516P)² + 0.2268P] where P = (F_o² + 2F_c²)/3
2126 reflections	(Δ/σ)_max = 0.003
181 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₀H₂Cl₄F₃NO₂	γ = 92.704 (3)°
M_r = 366.93	V = 617.9 (9) Å³
Triclinic, P1	Z = 2
a = 4.943 (4) Å	Mo Kα radiation
b = 10.759 (9) Å	µ = 0.99 mm⁻¹
c = 12.130 (11) Å	T = 113 K
α = 101.373 (19)°	0.20 × 0.08 × 0.06 mm
β = 101.18 (2)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2126 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	2033 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.943	R_int = 0.027
5139 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.07	Δρ_max = 0.33 e Å⁻³
2126 reflections	Δρ_min = −0.34 e Å⁻³
181 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	0.45684 (8)	0.62343 (4)	0.10599 (3)	0.01714 (14)
Cl2	0.43932 (10)	0.86631 (4)	0.29132 (4)	0.02492 (14)
Cl3	0.10966 (10)	0.85656 (4)	0.48243 (4)	0.02680 (15)
Cl4	−0.26190 (9)	0.61244 (4)	0.47757 (4)	0.01965 (14)
F1	0.1532 (2)	0.08394 (12)	0.15299 (12)	0.0368 (3)
F2	−0.2343 (3)	−0.03074 (10)	0.09326 (10)	0.0347 (3)
F3	−0.1393 (3)	0.08654 (11)	0.26249 (10)	0.0356 (3)
O1	0.1734 (2)	0.34347 (11)	0.05198 (10)	0.0189 (3)
O2	−0.4074 (2)	0.34517 (12)	0.30361 (11)	0.0209 (3)
N1	−0.1296 (3)	0.31251 (13)	0.16870 (12)	0.0157 (3)
C1	0.0657 (3)	0.38289 (16)	0.13115 (15)	0.0145 (3)
C2	0.1009 (3)	0.51129 (16)	0.20884 (14)	0.0140 (3)
C3	0.2573 (3)	0.61999 (16)	0.20684 (14)	0.0148 (3)
C4	0.2506 (3)	0.72884 (15)	0.29118 (15)	0.0165 (4)
C5	0.0966 (4)	0.72557 (16)	0.37583 (14)	0.0177 (4)
C6	−0.0662 (3)	0.61525 (16)	0.37516 (15)	0.0155 (3)
C7	−0.0635 (3)	0.50918 (16)	0.28992 (14)	0.0143 (3)
C8	−0.2256 (3)	0.38237 (16)	0.26155 (14)	0.0155 (4)
C9	−0.2519 (4)	0.18735 (16)	0.10544 (15)	0.0190 (4)
H9A	−0.2347	0.1774	0.0243	0.023*
H9B	−0.4515	0.1801	0.1069	0.023*
C10	−0.1160 (4)	0.08224 (17)	0.15460 (15)	0.0196 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0164 (2)	0.0208 (2)	0.0167 (2)	0.00139 (17)	0.00554 (17)	0.00765 (17)
Cl2	0.0304 (3)	0.0152 (2)	0.0292 (3)	−0.00270 (18)	0.0068 (2)	0.00546 (18)
Cl3	0.0384 (3)	0.0184 (2)	0.0217 (3)	0.00406 (19)	0.0080 (2)	−0.00242 (18)
Cl4	0.0217 (2)	0.0254 (2)	0.0152 (2)	0.00822 (18)	0.00803 (17)	0.00679 (17)
F1	0.0242 (6)	0.0350 (7)	0.0603 (9)	0.0079 (5)	0.0129 (6)	0.0260 (6)
F2	0.0502 (7)	0.0160 (5)	0.0319 (7)	−0.0055 (5)	0.0022 (5)	−0.0006 (5)
F3	0.0617 (8)	0.0289 (6)	0.0198 (6)	0.0048 (6)	0.0135 (5)	0.0085 (5)
O1	0.0202 (6)	0.0203 (6)	0.0168 (6)	0.0020 (5)	0.0072 (5)	0.0022 (5)
O2	0.0175 (6)	0.0244 (7)	0.0233 (7)	−0.0005 (5)	0.0089 (5)	0.0066 (5)
N1	0.0158 (7)	0.0148 (7)	0.0163 (7)	−0.0005 (6)	0.0040 (6)	0.0024 (6)
C1	0.0138 (8)	0.0155 (8)	0.0144 (8)	0.0028 (6)	0.0005 (6)	0.0056 (6)
C2	0.0129 (8)	0.0165 (8)	0.0131 (8)	0.0041 (6)	0.0011 (6)	0.0054 (6)
C3	0.0139 (8)	0.0187 (8)	0.0131 (8)	0.0031 (6)	0.0024 (6)	0.0066 (6)
C4	0.0177 (8)	0.0144 (8)	0.0176 (9)	0.0017 (7)	0.0006 (7)	0.0065 (7)
C5	0.0218 (9)	0.0157 (8)	0.0147 (9)	0.0070 (7)	0.0007 (7)	0.0026 (7)
C6	0.0154 (8)	0.0202 (8)	0.0127 (8)	0.0063 (7)	0.0033 (6)	0.0062 (7)
C7	0.0129 (8)	0.0174 (8)	0.0138 (8)	0.0049 (6)	0.0020 (6)	0.0065 (6)
C8	0.0148 (8)	0.0176 (8)	0.0146 (8)	0.0030 (6)	0.0018 (7)	0.0058 (7)
C9	0.0189 (9)	0.0174 (8)	0.0183 (9)	−0.0035 (7)	0.0018 (7)	0.0014 (7)
C10	0.0230 (9)	0.0179 (8)	0.0178 (9)	−0.0037 (7)	0.0065 (7)	0.0024 (7)

Geometric parameters (Å, º) top

Cl1—C3	1.719 (2)	C1—C2	1.492 (3)
Cl2—C4	1.711 (2)	C2—C3	1.378 (3)
Cl3—C5	1.704 (2)	C2—C7	1.395 (3)
Cl4—C6	1.720 (2)	C3—C4	1.401 (3)
F1—C10	1.334 (2)	C4—C5	1.396 (3)
F2—C10	1.334 (2)	C5—C6	1.400 (3)
F3—C10	1.328 (2)	C6—C7	1.383 (3)
O1—C1	1.202 (2)	C7—C8	1.492 (3)
O2—C8	1.205 (2)	C9—C10	1.506 (3)
N1—C1	1.397 (2)	C9—H9A	0.9900
N1—C8	1.402 (2)	C9—H9B	0.9900
N1—C9	1.450 (2)

C1—N1—C8	113.24 (14)	C5—C6—Cl4	120.78 (14)
C1—N1—C9	122.43 (15)	C6—C7—C2	121.03 (16)
C8—N1—C9	123.58 (14)	C6—C7—C8	130.65 (16)
O1—C1—N1	125.00 (16)	C2—C7—C8	108.26 (15)
O1—C1—C2	130.05 (16)	O2—C8—N1	125.42 (16)
N1—C1—C2	104.95 (15)	O2—C8—C7	129.62 (16)
C3—C2—C7	121.73 (16)	N1—C8—C7	104.90 (14)
C3—C2—C1	129.80 (17)	N1—C9—C10	112.25 (15)
C7—C2—C1	108.46 (15)	N1—C9—H9A	109.2
C2—C3—C4	117.61 (17)	C10—C9—H9A	109.2
C2—C3—Cl1	121.85 (14)	N1—C9—H9B	109.2
C4—C3—Cl1	120.54 (14)	C10—C9—H9B	109.2
C5—C4—C3	120.88 (16)	H9A—C9—H9B	107.9
C5—C4—Cl2	119.90 (13)	F3—C10—F1	107.19 (15)
C3—C4—Cl2	119.21 (14)	F3—C10—F2	106.91 (15)
C4—C5—C6	120.82 (16)	F1—C10—F2	107.04 (15)
C4—C5—Cl3	119.78 (14)	F3—C10—C9	112.72 (16)
C6—C5—Cl3	119.40 (15)	F1—C10—C9	112.66 (15)
C7—C6—C5	117.84 (17)	F2—C10—C9	109.98 (16)
C7—C6—Cl4	121.38 (14)

C8—N1—C1—O1	−178.89 (16)	Cl3—C5—C6—Cl4	2.3 (2)
C9—N1—C1—O1	−8.4 (3)	C5—C6—C7—C2	1.4 (2)
C8—N1—C1—C2	0.56 (18)	Cl4—C6—C7—C2	−178.43 (12)
C9—N1—C1—C2	171.02 (14)	C5—C6—C7—C8	−175.42 (16)
O1—C1—C2—C3	3.2 (3)	Cl4—C6—C7—C8	4.7 (3)
N1—C1—C2—C3	−176.17 (16)	C3—C2—C7—C6	−3.0 (2)
O1—C1—C2—C7	−178.26 (17)	C1—C2—C7—C6	178.38 (14)
N1—C1—C2—C7	2.33 (17)	C3—C2—C7—C8	174.49 (15)
C7—C2—C3—C4	1.3 (2)	C1—C2—C7—C8	−4.16 (18)
C1—C2—C3—C4	179.68 (15)	C1—N1—C8—O2	174.66 (16)
C7—C2—C3—Cl1	−179.20 (12)	C9—N1—C8—O2	4.3 (3)
C1—C2—C3—Cl1	−0.9 (3)	C1—N1—C8—C7	−3.00 (17)
C2—C3—C4—C5	1.7 (2)	C9—N1—C8—C7	−173.33 (14)
Cl1—C3—C4—C5	−177.73 (12)	C6—C7—C8—O2	4.0 (3)
C2—C3—C4—Cl2	−179.49 (12)	C2—C7—C8—O2	−173.14 (17)
Cl1—C3—C4—Cl2	1.0 (2)	C6—C7—C8—N1	−178.48 (17)
C3—C4—C5—C6	−3.3 (3)	C2—C7—C8—N1	4.39 (17)
Cl2—C4—C5—C6	177.95 (13)	C1—N1—C9—C10	99.37 (19)
C3—C4—C5—Cl3	175.92 (13)	C8—N1—C9—C10	−91.2 (2)
Cl2—C4—C5—Cl3	−2.8 (2)	N1—C9—C10—F3	61.1 (2)
C4—C5—C6—C7	1.7 (2)	N1—C9—C10—F1	−60.4 (2)
Cl3—C5—C6—C7	−177.55 (12)	N1—C9—C10—F2	−179.68 (14)
C4—C5—C6—Cl4	−178.51 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···F1ⁱ	0.99	2.38	3.289 (4)	152

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₂Cl₄F₃NO₂
M_r	366.93
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	4.943 (4), 10.759 (9), 12.130 (11)
α, β, γ (°)	101.373 (19), 101.18 (2), 92.704 (3)
V (Å³)	617.9 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.20 × 0.08 × 0.06

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2001)
T_min, T_max	0.826, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	5139, 2126, 2033
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.078, 1.07
No. of reflections	2126
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34

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
C9—H9B···F1ⁱ	0.99	2.38	3.289 (4)	152

Symmetry code: (i) x−1, y, z.

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
Valkonen, A., Lahtinen, T. & Rissanen, K. (2007). Acta Cryst. E63, o472–o473. Web of Science CSD CrossRef IUCr Journals Google Scholar