2-(2,2,2-Trifluoro-eth-yl)isoindoline-1,3-dione.

In the title compound, C(10)H(6)F(3)NO(2), the isoindole ring system is planar, the maximum atomic deviation being 0.012 (2) Å. The C-C bond of the trifluoro-ethyl group is twisted with respect to the isoindole ring by a dihedral angle of 62.58 (17)°. Weak inter-molecular 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 = 229.16

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.126

S = 0.97

1608 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.50 e Å−3

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 ▶).

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

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

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

C10H6F3NO2	F(000) = 464
Mr = 229.16	Dx = 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

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

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(Fo2) + (0.0618P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
1608 reflections	Δρmax = 0.43 e Å−3
146 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .