Related literature {#sec1}
==================

The title compound is a key inter­mediate in the synthesis of organic electro-luminescent materials, see: Han & Kay (2005[@bb2]). For the synthesis, see: Valkonen *et al.* (2007[@bb5]); Barchin *et al.* (2002[@bb1]). For a related structure, see: Valkonen *et al.* (2007[@bb5]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~10~H~6~F~3~NO~2~*M* *~r~* = 229.16Monoclinic,*a* = 5.047 (1) Å*b* = 9.5370 (19) Å*c* = 19.051 (4) Åβ = 95.20 (3)°*V* = 913.2 (3) Å^3^*Z* = 4Mo *K*α radiationμ = 0.16 mm^−1^*T* = 113 K0.26 × 0.18 × 0.14 mm

### Data collection {#sec2.1.2}

Rigaku Saturn CCD area-detector diffractometerAbsorption correction: multi-scan (*CrystalClear*; Rigaku, 2005[@bb3]) *T* ~min~ = 0.960, *T* ~max~ = 0.9787732 measured reflections1608 independent reflections1009 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.083

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.055*wR*(*F* ^2^) = 0.126*S* = 0.971608 reflections146 parametersH-atom parameters constrainedΔρ~max~ = 0.43 e Å^−3^Δρ~min~ = −0.50 e Å^−3^

 {#d5e465}

Data collection: *CrystalClear* (Rigaku, 2005[@bb3]); cell refinement: *CrystalClear*; data reduction: *CrystalClear*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb4]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb4]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb4]); software used to prepare material for publication: *CrystalStructure* (Rigaku, 2005[@bb3]).

Supplementary Material
======================

Crystal structure: contains datablocks I, global. DOI: [10.1107/S1600536810020222/sj5001sup1.cif](http://dx.doi.org/10.1107/S1600536810020222/sj5001sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536810020222/sj5001Isup2.hkl](http://dx.doi.org/10.1107/S1600536810020222/sj5001Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?sj5001&file=sj5001sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?sj5001sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?sj5001&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [SJ5001](http://scripts.iucr.org/cgi-bin/sendsup?sj5001)).

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).

Comment
=======

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.

Experimental {#experimental}
============

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.

Refinement {#refinement}
==========

H atoms were positioned geometrically and refined as riding with C---H = 0.95 or 0.99 Å, and U~iso~(H) = 1.2U~eq~(C).

Figures
=======

![The molecule of I showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.](e-66-o1745-fig1){#Fap1}

![Crystal packing of I viewed down the a axis with hydrogen bonds drawn as dashed lines.](e-66-o1745-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------- ---------------------------------------
  C~10~H~6~F~3~NO~2~        *F*(000) = 464
  *M~r~* = 229.16           *D*~x~ = 1.667 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Melting point: 400 K
  Hall symbol: -P 2ybc      Mo *K*α 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) Å^3^      Prism, colorless
  *Z* = 4                   0.26 × 0.18 × 0.14 mm
  ------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------------ --------------------------------------
  Rigaku Saturn CCD area-detector diffractometer                     1608 independent reflections
  Radiation source: rotating anode                                   1009 reflections with *I* \> 2σ(*I*)
  multilayer                                                         *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 {#tablewraprefinementdatalong}
==========

  ---------------------------------------------------------------- ----------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                                             Secondary atom site location: difference Fourier map
  Least-squares matrix: full                                       Hydrogen site location: inferred from neighbouring sites
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.055                              H-atom parameters constrained
  *wR*(*F*^2^) = 0.126                                             *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0618*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/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\[1+0.001xFc^2^λ^3^/sin(2θ)\]^-1/4^
  Primary atom site location: structure-invariant direct methods   Extinction coefficient: 0.301 (15)
  ---------------------------------------------------------------- ----------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  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 *F*^2^ against ALL reflections. The weighted *R*-factor wR and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) etc. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ 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 (Å^2^) {#tablewrapcoords}
==================================================================================================

  ----- ------------ -------------- -------------- -------------------- --
        *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 (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- ------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^       *U*^13^        *U*^23^
  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, °) {#tablewrapgeomlong}
===========================

  ------------------- ------------ -------------------- ------------
  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, °) {#tablewraphbondslong}
=============================

  -------------------- --------- --------- ----------- ---------------
  *D*---H···*A*        *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C6---H6···O2^i^      0.95      2.52      3.462 (3)   174
  C4---H4···O1^ii^     0.95      2.60      3.229 (3)   124
  C9---H9B···O2^iii^   0.99      2.54      3.311 (3)   135
  C3---H3···F3^ii^     0.95      2.62      3.556 (3)   168
  C3---H3···O1^ii^     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*.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*          *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  -------------------- --------- ------- ----------- -------------
  C6---H6⋯O2^i^        0.95      2.52    3.462 (3)   174
  C4---H4⋯O1^ii^       0.95      2.60    3.229 (3)   124
  C9---H9*B*⋯O2^iii^   0.99      2.54    3.311 (3)   135
  C3---H3⋯F3^ii^       0.95      2.62    3.556 (3)   168
  C3---H3⋯O1^ii^       0.95      2.66    3.247 (3)   120

Symmetry codes: (i) ; (ii) ; (iii) .
