2-(2,2,2-Trifluoro­eth­yl)isoindoline-1,3-dione

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

doi:10.1107/S1600536810020222

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1745

doi:10.1107/S1600536810020222

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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 12 May 2010; accepted 28 May 2010; online 23 June 2010)

In the title compound, C₁₀H₆F₃NO₂, the isoindole ring system is planar, the maximum atomic deviation being 0.012 (2) Å. The C—C bond of the trifluoroethyl group is twisted with respect to the isoindole ring by a dihedral angle of 62.58 (17)°. Weak intermolecular C—H⋯O and C—H⋯F hydrogen bonding is 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 ). For the synthesis, see: Valkonen et al. (2007 ); Barchin et al. (2002 ). For a related structure, see: Valkonen et al. (2007).

Experimental

Crystal data

C₁₀H₆F₃NO₂
M_r = 229.16
Monoclinic, P 2₁ /c
a = 5.047 (1) Å
b = 9.5370 (19) Å
c = 19.051 (4) Å
β = 95.20 (3)°
V = 913.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 113 K
0.26 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.960, T_max = 0.978
7732 measured reflections
1608 independent reflections
1009 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.126
S = 0.97
1608 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.95	2.52	3.462 (3)	174
C4—H4⋯O1ⁱⁱ	0.95	2.60	3.229 (3)	124
C9—H9B⋯O2ⁱⁱⁱ	0.99	2.54	3.311 (3)	135
C3—H3⋯F3ⁱⁱ	0.95	2.62	3.556 (3)	168
C3—H3⋯O1ⁱⁱ	0.95	2.66	3.247 (3)	120
Symmetry codes: (i) -x, -y+1, -z; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku, 2005).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020222/sj5001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020222/sj5001Isup2.hkl

checkCIF report

Comment top

The title compound, I, 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 widely 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 0.012 (2) Å (for the N1 atom). The C9—C10 bond of the trifluoroethyl group is twisted with respect to the isoindole ring by a dihedral angle of 62.58 (17)°, which is similar to the angle 60.3 (5)° found in the related compound 2-(2-iodoethyl)isoindole-1,3-dione (Valkonen et al. 2007). Weak intermolecular C—H···O and and C—H···F hydrogen bonding is present in the crystal structure, Table 1, Fig. 2.

Related literature top

The title compound is a key intermediate in the synthesis of organic electro-luminescent materials, see: Han & Kay (2005). For the synthesis, see: Valkonen et al. (2007); Barchin et al. (2002). For a related structure, see: Valkonen et al. (2007).

Experimental top

An acetic acid solution of phthalic anhydride (14.8 g, 100 mmol) and 2,2,2-trifluoroethylamine (7.99 ml, 100 mmol) was refluxed overnight, and then filtered. The crude product was recrystallized from ethyl acetate.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: CrystalStructure (Rigaku, 2005).

Figures top

	Fig. 1. The molecule of I showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of I viewed down the a axis with hydrogen bonds drawn as dashed lines.

2-(2,2,2-Trifluoroethyl)isoindoline-1,3-dione top

Crystal data top

C₁₀H₆F₃NO₂	F(000) = 464
M_r = 229.16	D_x = 1.667 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 400 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71075 Å
a = 5.047 (1) Å	Cell parameters from 2545 reflections
b = 9.5370 (19) Å	θ = 2.1–28.0°
c = 19.051 (4) Å	µ = 0.16 mm⁻¹
β = 95.20 (3)°	T = 113 K
V = 913.2 (3) Å³	Prism, colorless
Z = 4	0.26 × 0.18 × 0.14 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1608 independent reflections
Radiation source: rotating anode	1009 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.083
ω and ϕ scans	θ_max = 25.2°, θ_min = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −6→5
T_min = 0.960, T_max = 0.978	k = −11→11
7732 measured reflections	l = −22→22

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0618P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
1608 reflections	Δρ_max = 0.43 e Å⁻³
146 parameters	Δρ_min = −0.50 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: 0.301 (15)

Crystal data top

C₁₀H₆F₃NO₂	V = 913.2 (3) Å³
M_r = 229.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.047 (1) Å	µ = 0.16 mm⁻¹
b = 9.5370 (19) Å	T = 113 K
c = 19.051 (4) Å	0.26 × 0.18 × 0.14 mm
β = 95.20 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1608 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1009 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.978	R_int = 0.083
7732 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 0.97	Δρ_max = 0.43 e Å⁻³
1608 reflections	Δρ_min = −0.50 e Å⁻³
146 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
F1	0.3850 (3)	0.94405 (16)	0.09725 (9)	0.0441 (5)
F2	0.7282 (3)	1.04965 (15)	0.06326 (9)	0.0434 (6)
F3	0.7509 (3)	0.94503 (15)	0.16352 (8)	0.0424 (5)
O1	1.0018 (3)	0.65493 (18)	0.17852 (9)	0.0311 (5)
O2	0.2715 (3)	0.63673 (19)	0.01945 (9)	0.0327 (6)
N1	0.6488 (4)	0.6796 (2)	0.09384 (11)	0.0258 (6)
C1	0.7960 (5)	0.6112 (3)	0.14966 (14)	0.0259 (7)
C2	0.6475 (5)	0.4813 (3)	0.16200 (13)	0.0249 (7)
C3	0.7001 (5)	0.3752 (3)	0.21083 (14)	0.0288 (7)
H3	0.8508	0.3792	0.2445	0.035*
C4	0.5253 (5)	0.2632 (3)	0.20895 (14)	0.0306 (7)
H4	0.5581	0.1884	0.2416	0.037*
C5	0.3044 (5)	0.2576 (3)	0.16073 (15)	0.0316 (7)
H5	0.1870	0.1798	0.1611	0.038*
C6	0.2508 (5)	0.3642 (3)	0.11158 (14)	0.0289 (7)
H6	0.0992	0.3609	0.0782	0.035*
C7	0.4270 (5)	0.4746 (3)	0.11336 (13)	0.0258 (7)
C8	0.4261 (5)	0.6019 (3)	0.06811 (14)	0.0264 (7)
C9	0.7342 (5)	0.8059 (3)	0.06062 (14)	0.0296 (7)
H9A	0.6593	0.8074	0.0108	0.036*
H9B	0.9306	0.8055	0.0613	0.036*
C10	0.6488 (6)	0.9351 (3)	0.09660 (15)	0.0326 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0356 (11)	0.0349 (10)	0.0619 (13)	0.0086 (8)	0.0059 (8)	−0.0084 (8)
F2	0.0571 (13)	0.0238 (10)	0.0492 (12)	−0.0014 (8)	0.0039 (9)	0.0066 (7)
F3	0.0596 (13)	0.0298 (10)	0.0362 (11)	0.0038 (8)	−0.0051 (9)	−0.0039 (7)
O1	0.0285 (12)	0.0274 (11)	0.0361 (11)	0.0003 (9)	−0.0034 (9)	−0.0039 (8)
O2	0.0298 (12)	0.0350 (12)	0.0321 (12)	0.0042 (8)	−0.0040 (9)	0.0001 (9)
N1	0.0227 (13)	0.0211 (12)	0.0329 (13)	0.0022 (10)	−0.0022 (10)	0.0009 (10)
C1	0.0249 (16)	0.0237 (15)	0.0288 (15)	0.0043 (13)	0.0003 (12)	−0.0047 (11)
C2	0.0213 (15)	0.0247 (15)	0.0287 (15)	0.0059 (12)	0.0015 (12)	−0.0037 (11)
C3	0.0277 (17)	0.0281 (16)	0.0305 (16)	0.0069 (13)	0.0012 (12)	−0.0020 (12)
C4	0.0331 (18)	0.0248 (16)	0.0347 (17)	0.0052 (13)	0.0081 (13)	0.0022 (12)
C5	0.0283 (17)	0.0250 (16)	0.0423 (18)	0.0009 (13)	0.0073 (14)	−0.0057 (12)
C6	0.0261 (17)	0.0277 (16)	0.0327 (16)	0.0018 (13)	0.0018 (12)	−0.0072 (12)
C7	0.0245 (16)	0.0232 (15)	0.0303 (16)	0.0038 (12)	0.0053 (12)	−0.0040 (12)
C8	0.0230 (16)	0.0255 (15)	0.0305 (16)	0.0057 (12)	0.0011 (12)	−0.0051 (12)
C9	0.0302 (16)	0.0237 (15)	0.0347 (17)	0.0021 (13)	0.0018 (12)	0.0027 (12)
C10	0.0340 (19)	0.0238 (16)	0.0389 (18)	0.0009 (14)	−0.0022 (13)	0.0032 (12)

Geometric parameters (Å, º) top

F1—C10	1.335 (3)	C3—H3	0.9500
F2—C10	1.343 (3)	C4—C5	1.380 (3)
F3—C10	1.334 (3)	C4—H4	0.9500
O1—C1	1.205 (3)	C5—C6	1.392 (4)
O2—C8	1.203 (3)	C5—H5	0.9500
N1—C8	1.398 (3)	C6—C7	1.376 (3)
N1—C1	1.402 (3)	C6—H6	0.9500
N1—C9	1.445 (3)	C7—C8	1.489 (4)
C1—C2	1.478 (4)	C9—C10	1.492 (4)
C2—C3	1.384 (3)	C9—H9A	0.9900
C2—C7	1.383 (3)	C9—H9B	0.9900
C3—C4	1.384 (4)

C8—N1—C1	111.9 (2)	C5—C6—H6	121.4
C8—N1—C9	123.4 (2)	C6—C7—C2	122.0 (2)
C1—N1—C9	124.2 (2)	C6—C7—C8	129.9 (2)
O1—C1—N1	124.1 (2)	C2—C7—C8	108.1 (2)
O1—C1—C2	130.3 (2)	O2—C8—N1	124.6 (2)
N1—C1—C2	105.6 (2)	O2—C8—C7	129.7 (2)
C3—C2—C7	120.7 (2)	N1—C8—C7	105.6 (2)
C3—C2—C1	130.6 (2)	N1—C9—C10	112.2 (2)
C7—C2—C1	108.7 (2)	N1—C9—H9A	109.2
C2—C3—C4	117.7 (2)	C10—C9—H9A	109.2
C2—C3—H3	121.2	N1—C9—H9B	109.2
C4—C3—H3	121.2	C10—C9—H9B	109.2
C5—C4—C3	121.4 (2)	H9A—C9—H9B	107.9
C5—C4—H4	119.3	F3—C10—F1	106.6 (2)
C3—C4—H4	119.3	F3—C10—F2	106.8 (2)
C4—C5—C6	121.1 (2)	F1—C10—F2	107.0 (2)
C4—C5—H5	119.5	F3—C10—C9	113.3 (2)
C6—C5—H5	119.5	F1—C10—C9	112.8 (2)
C7—C6—C5	117.1 (2)	F2—C10—C9	110.1 (2)
C7—C6—H6	121.4

C8—N1—C1—O1	176.9 (2)	C1—C2—C7—C6	179.5 (2)
C9—N1—C1—O1	4.5 (4)	C3—C2—C7—C8	−179.4 (2)
C8—N1—C1—C2	−2.3 (3)	C1—C2—C7—C8	−0.4 (3)
C9—N1—C1—C2	−174.7 (2)	C1—N1—C8—O2	−178.4 (2)
O1—C1—C2—C3	1.4 (5)	C9—N1—C8—O2	−6.0 (4)
N1—C1—C2—C3	−179.5 (3)	C1—N1—C8—C7	2.0 (3)
O1—C1—C2—C7	−177.6 (3)	C9—N1—C8—C7	174.5 (2)
N1—C1—C2—C7	1.6 (3)	C6—C7—C8—O2	−0.4 (5)
C7—C2—C3—C4	0.1 (4)	C2—C7—C8—O2	179.5 (3)
C1—C2—C3—C4	−178.7 (3)	C6—C7—C8—N1	179.1 (3)
C2—C3—C4—C5	−0.7 (4)	C2—C7—C8—N1	−1.0 (3)
C3—C4—C5—C6	0.7 (4)	C8—N1—C9—C10	100.0 (3)
C4—C5—C6—C7	−0.1 (4)	C1—N1—C9—C10	−88.4 (3)
C5—C6—C7—C2	−0.5 (4)	N1—C9—C10—F3	61.7 (3)
C5—C6—C7—C8	179.4 (3)	N1—C9—C10—F1	−59.5 (3)
C3—C2—C7—C6	0.5 (4)	N1—C9—C10—F2	−178.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.52	3.462 (3)	174
C4—H4···O1ⁱⁱ	0.95	2.60	3.229 (3)	124
C9—H9B···O2ⁱⁱⁱ	0.99	2.54	3.311 (3)	135
C3—H3···F3ⁱⁱ	0.95	2.62	3.556 (3)	168
C3—H3···O1ⁱⁱ	0.95	2.66	3.247 (3)	120

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

Experimental details

Crystal data
Chemical formula	C₁₀H₆F₃NO₂
M_r	229.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	5.047 (1), 9.5370 (19), 19.051 (4)
β (°)	95.20 (3)
V (Å³)	913.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.26 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.960, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	7732, 1608, 1009
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.126, 0.97
No. of reflections	1608
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.50

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.52	3.462 (3)	174
C4—H4···O1ⁱⁱ	0.95	2.60	3.229 (3)	124
C9—H9B···O2ⁱⁱⁱ	0.99	2.54	3.311 (3)	135
C3—H3···F3ⁱⁱ	0.95	2.62	3.556 (3)	168
C3—H3···O1ⁱⁱ	0.95	2.66	3.247 (3)	120

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

Acknowledgements

This 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

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