Acta Cryst. (2008). E64, o388 [ doi:10.1107/S1600536807068249 ]
The molecule of the title compound, C31H16F6N2O4, consists of two phthalimide units linked by a [bis(trifluoromethyl)methylene]di-p-phenylene bridge, with the two halves of the molecule related to each other by a twofold rotation axis. The dihedral angle between the planes of the two central benzene rings is 70.5 (3)°. The terminal isoindole groups are approximately planar, with a maximum r.m.s. deviation of 0.006 Å from the mean plane, and they form dihedral angles of 46.03 (3)° to the attached benzene rings. Intermolecular C-H
O hydrogen bonds link neighboring molecules into chains along the c axis.
A solution of phthaloyl dichoride (420 mg, 2 mmol) was added slowly over a period of 10 min to a solution of 4-(2-(4-aminophenyl)-1,1,1,3,3,3- hexafluoropropan-2-yl)benzenamine (334 mg, 1 mmol) in dichloromethane (25 ml) at 273 K to yield a light yellow precipitate. Triethylamine (5 ml) was then added to dissolve the precipitate which became a yellow suspension after stirring for 12 h. The compound was filtered and dried to give (I), (yield 362 mg, 61%). Single crystals of (I) were obtained by recrystallization from DMF at room temperature.
Non-hydrogen atoms were refined with anisotropic displacement parameters. One of the trifluoromethyl groups (C1/F1/F2/F3) of the title compound was found to be disordered over two orientations. The occupancies of the disordered positions C1/C1', F1/F1', F2/F2'and F3/F3' were refined to 0.59 (5) /0.41 (5). All H atoms were initially located in a difference Fourier map and then included with constrained bond lengths and isotropic displacement parameters: C—H=0.93Å and Uiso(H)=1.2Ueq(C) for aromatic H atoms.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
![[Figure 1]](./ez2112fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing atom labels with 50% probability displacement ellipsoids. |
| C31H16F6N2O4 | F000 = 1208 |
| Mr = 594.46 | Dx = 1.493 Mg m−3 |
| Orthorhombic, Pcca | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2a 2ac | Cell parameters from 2679 reflections |
| a = 13.3588 (19) Å | θ = 2.6–21.8º |
| b = 12.5340 (18) Å | µ = 0.13 mm−1 |
| c = 15.792 (2) Å | T = 292 (2) K |
| V = 2644.2 (6) Å3 | Block, colorless |
| Z = 4 | 0.30 × 0.30 × 0.20 mm |
| Bruker SMART 4K CCD area-detector diffractometer | 1864 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.119 |
| Monochromator: graphite | θmax = 26.0º |
| T = 292(2) K | θmin = 2.6º |
| φ and ω scans | h = −16→16 |
| Absorption correction: none | k = −15→13 |
| 15610 measured reflections | l = −19→19 |
| 2607 independent reflections |
| 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)] = 0.066 | H-atom parameters constrained |
| wR(F2) = 0.168 | w = 1/[σ2(Fo2) + (0.0607P)2 + 1.4164P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 2607 reflections | Δρmax = 0.24 e Å−3 |
| 232 parameters | Δρmin = −0.23 e Å−3 |
| 64 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C31H16F6N2O4 | V = 2644.2 (6) Å3 |
| Mr = 594.46 | Z = 4 |
| Orthorhombic, Pcca | Mo Kα |
| a = 13.3588 (19) Å | µ = 0.13 mm−1 |
| b = 12.5340 (18) Å | T = 292 (2) K |
| c = 15.792 (2) Å | 0.30 × 0.30 × 0.20 mm |
| Bruker SMART 4K CCD area-detector diffractometer | 2607 independent reflections |
| Absorption correction: none | 1864 reflections with I > 2σ(I) |
| 15610 measured reflections | Rint = 0.119 |
| R[F2 > 2σ(F2)] = 0.066 | 64 restraints |
| wR(F2) = 0.168 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.24 e Å−3 |
| 2607 reflections | Δρmin = −0.23 e Å−3 |
| 232 parameters |
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. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| C1 | 0.1413 (6) | 0.5169 (6) | 0.0925 (5) | 0.061 (3) | 0.59 |
| F1 | 0.1409 (5) | 0.5845 (3) | 0.0233 (3) | 0.110 (2) | 0.59 |
| F2 | 0.0992 (5) | 0.4244 (3) | 0.0577 (3) | 0.115 (2) | 0.59 |
| F3 | 0.0585 (4) | 0.5547 (4) | 0.1406 (4) | 0.0905 (18) | 0.59 |
| C1' | 0.1891 (7) | 0.5093 (6) | 0.0641 (4) | 0.067 (3) | 0.41 |
| F1' | 0.2253 (6) | 0.5779 (5) | 0.0078 (4) | 0.088 (2) | 0.41 |
| F2' | 0.1774 (6) | 0.4132 (4) | 0.0295 (4) | 0.083 (2) | 0.41 |
| F3' | 0.1045 (5) | 0.5408 (7) | 0.1022 (6) | 0.072 (3) | 0.41 |
| C2 | 0.2500 | 0.5000 | 0.1377 (3) | 0.089 (2) | |
| C3 | 0.2705 (3) | 0.6000 (2) | 0.1916 (2) | 0.0590 (10) | |
| C4 | 0.2369 (3) | 0.7005 (3) | 0.1690 (2) | 0.0572 (10) | |
| H4 | 0.1967 | 0.7089 | 0.1214 | 0.069* | |
| C5 | 0.3309 (3) | 0.5905 (3) | 0.2625 (2) | 0.0641 (11) | |
| H5 | 0.3531 | 0.5233 | 0.2788 | 0.077* | |
| C6 | 0.2630 (3) | 0.7884 (2) | 0.21707 (19) | 0.0460 (8) | |
| H6 | 0.2388 | 0.8554 | 0.2022 | 0.055* | |
| C7 | 0.3592 (3) | 0.6783 (3) | 0.3097 (2) | 0.0555 (9) | |
| H7 | 0.4011 | 0.6706 | 0.3564 | 0.067* | |
| C8 | 0.3240 (2) | 0.7780 (2) | 0.28632 (19) | 0.0419 (7) | |
| C9 | 0.3798 (2) | 0.9679 (2) | 0.29929 (19) | 0.0414 (7) | |
| C10 | 0.3466 (2) | 0.8763 (3) | 0.42443 (19) | 0.0414 (7) | |
| C11 | 0.3948 (2) | 1.0421 (2) | 0.37121 (19) | 0.0404 (7) | |
| C12 | 0.4248 (3) | 1.1469 (3) | 0.3716 (2) | 0.0517 (9) | |
| H12 | 0.4403 | 1.1826 | 0.3217 | 0.062* | |
| C13 | 0.4310 (3) | 1.1972 (3) | 0.4497 (2) | 0.0595 (10) | |
| H13 | 0.4506 | 1.2683 | 0.4522 | 0.071* | |
| C14 | 0.4084 (3) | 1.1434 (3) | 0.5240 (2) | 0.0560 (10) | |
| H14 | 0.4129 | 1.1791 | 0.5755 | 0.067* | |
| C15 | 0.3795 (2) | 1.0383 (3) | 0.5228 (2) | 0.0500 (9) | |
| H15 | 0.3648 | 1.0021 | 0.5726 | 0.060* | |
| C16 | 0.3731 (2) | 0.9880 (2) | 0.44536 (18) | 0.0382 (7) | |
| N1 | 0.35108 (19) | 0.86997 (19) | 0.33529 (15) | 0.0405 (6) | |
| O1 | 0.38753 (18) | 0.98510 (18) | 0.22441 (13) | 0.0569 (7) | |
| O3 | 0.32502 (19) | 0.80458 (19) | 0.47064 (14) | 0.0570 (7) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.104 (8) | 0.039 (5) | 0.040 (4) | 0.000 (5) | −0.012 (5) | 0.007 (4) |
| F1 | 0.228 (7) | 0.043 (2) | 0.060 (3) | −0.030 (4) | −0.054 (4) | 0.018 (2) |
| F2 | 0.200 (6) | 0.041 (2) | 0.105 (4) | −0.026 (3) | −0.081 (5) | 0.001 (2) |
| F3 | 0.091 (4) | 0.067 (3) | 0.114 (5) | −0.007 (3) | −0.036 (3) | 0.013 (3) |
| C1' | 0.129 (8) | 0.038 (5) | 0.033 (5) | −0.027 (6) | 0.005 (5) | −0.008 (4) |
| F1' | 0.146 (6) | 0.055 (4) | 0.061 (4) | −0.008 (5) | −0.025 (5) | 0.007 (3) |
| F2' | 0.120 (5) | 0.053 (4) | 0.075 (5) | −0.010 (4) | −0.040 (4) | −0.014 (3) |
| F3' | 0.046 (5) | 0.055 (5) | 0.115 (8) | 0.016 (4) | −0.029 (4) | −0.005 (5) |
| C2 | 0.199 (8) | 0.028 (3) | 0.039 (3) | −0.018 (4) | 0.000 | 0.000 |
| C3 | 0.107 (3) | 0.0301 (17) | 0.0400 (19) | −0.0091 (18) | 0.004 (2) | 0.0000 (14) |
| C4 | 0.095 (3) | 0.0373 (18) | 0.0391 (18) | −0.0116 (18) | −0.0078 (19) | 0.0001 (14) |
| C5 | 0.111 (3) | 0.0280 (17) | 0.053 (2) | 0.0087 (18) | −0.003 (2) | 0.0038 (15) |
| C6 | 0.071 (2) | 0.0292 (15) | 0.0377 (17) | −0.0012 (15) | −0.0008 (16) | 0.0028 (13) |
| C7 | 0.076 (2) | 0.0424 (19) | 0.048 (2) | 0.0042 (17) | −0.0049 (18) | 0.0026 (16) |
| C8 | 0.0587 (19) | 0.0338 (16) | 0.0333 (16) | −0.0039 (14) | 0.0052 (15) | −0.0013 (13) |
| C9 | 0.0523 (19) | 0.0385 (17) | 0.0333 (17) | −0.0040 (14) | 0.0012 (14) | 0.0000 (13) |
| C10 | 0.0429 (17) | 0.0455 (19) | 0.0358 (17) | 0.0020 (14) | 0.0023 (13) | 0.0026 (15) |
| C11 | 0.0427 (16) | 0.0434 (18) | 0.0351 (17) | −0.0030 (13) | 0.0015 (14) | −0.0020 (13) |
| C12 | 0.063 (2) | 0.0432 (19) | 0.049 (2) | −0.0073 (16) | 0.0010 (17) | −0.0029 (16) |
| C13 | 0.062 (2) | 0.049 (2) | 0.068 (3) | −0.0036 (17) | −0.0006 (19) | −0.0192 (19) |
| C14 | 0.0503 (19) | 0.068 (3) | 0.049 (2) | 0.0047 (17) | −0.0017 (16) | −0.0275 (18) |
| C15 | 0.0458 (18) | 0.068 (2) | 0.0362 (18) | 0.0035 (16) | −0.0020 (15) | −0.0117 (16) |
| C16 | 0.0369 (16) | 0.0454 (18) | 0.0322 (15) | 0.0037 (13) | −0.0015 (13) | −0.0020 (13) |
| N1 | 0.0558 (15) | 0.0345 (14) | 0.0313 (14) | −0.0033 (12) | −0.0005 (12) | −0.0015 (11) |
| O1 | 0.0885 (18) | 0.0518 (14) | 0.0305 (12) | −0.0178 (12) | 0.0006 (12) | 0.0018 (10) |
| O3 | 0.0754 (16) | 0.0545 (15) | 0.0411 (13) | −0.0073 (12) | 0.0015 (12) | 0.0129 (11) |
| C1—F1 | 1.382 (7) | C5—H5 | 0.9300 |
| C1—F2 | 1.401 (8) | C6—C8 | 1.370 (4) |
| C1—F3 | 1.422 (8) | C6—H6 | 0.9300 |
| C1—C2 | 1.632 (7) | C7—C8 | 1.386 (4) |
| C1'—F1' | 1.329 (8) | C7—H7 | 0.9300 |
| C1'—F2' | 1.332 (7) | C8—N1 | 1.434 (4) |
| C1'—F3' | 1.339 (8) | C9—O1 | 1.207 (4) |
| C1'—C2 | 1.423 (7) | C9—N1 | 1.406 (4) |
| C1'—C1'i | 1.645 (18) | C9—C11 | 1.482 (4) |
| C1'—F1'i | 1.815 (12) | C10—O3 | 1.194 (4) |
| F1'—F2'i | 1.350 (11) | C10—N1 | 1.411 (4) |
| F1'—C1'i | 1.815 (12) | C10—C16 | 1.481 (4) |
| F2'—F1'i | 1.350 (11) | C11—C12 | 1.373 (4) |
| C2—C1'i | 1.423 (7) | C11—C16 | 1.383 (4) |
| C2—C3 | 1.540 (4) | C12—C13 | 1.387 (5) |
| C2—C3i | 1.540 (4) | C12—H12 | 0.9300 |
| C2—C1i | 1.632 (7) | C13—C14 | 1.386 (5) |
| C3—C4 | 1.384 (5) | C13—H13 | 0.9300 |
| C3—C5 | 1.386 (5) | C14—C15 | 1.374 (5) |
| C4—C6 | 1.383 (4) | C14—H14 | 0.9300 |
| C4—H4 | 0.9300 | C15—C16 | 1.378 (4) |
| C5—C7 | 1.381 (5) | C15—H15 | 0.9300 |
| F1—C1—F2 | 101.3 (5) | C6—C4—C3 | 120.1 (3) |
| F1—C1—F3 | 102.4 (6) | C6—C4—H4 | 119.9 |
| F2—C1—F3 | 100.0 (6) | C3—C4—H4 | 119.9 |
| F1—C1—C2 | 115.3 (6) | C7—C5—C3 | 121.8 (3) |
| F2—C1—C2 | 114.9 (5) | C7—C5—H5 | 119.1 |
| F3—C1—C2 | 120.1 (6) | C3—C5—H5 | 119.1 |
| F1'—C1'—F2' | 110.6 (6) | C8—C6—C4 | 120.8 (3) |
| F1'—C1'—F3' | 114.7 (8) | C8—C6—H6 | 119.6 |
| F2'—C1'—F3' | 110.6 (7) | C4—C6—H6 | 119.6 |
| F1'—C1'—C2 | 113.0 (6) | C5—C7—C8 | 118.8 (3) |
| F2'—C1'—C2 | 109.2 (7) | C5—C7—H7 | 120.6 |
| F3'—C1'—C2 | 98.1 (6) | C8—C7—H7 | 120.6 |
| F1'—C1'—C1'i | 74.4 (6) | C6—C8—C7 | 120.0 (3) |
| F2'—C1'—C1'i | 89.3 (7) | C6—C8—N1 | 120.3 (3) |
| F3'—C1'—C1'i | 151.2 (6) | C7—C8—N1 | 119.7 (3) |
| C2—C1'—C1'i | 54.7 (4) | O1—C9—N1 | 125.2 (3) |
| F1'—C1'—F1'i | 80.3 (6) | O1—C9—C11 | 128.9 (3) |
| F2'—C1'—F1'i | 47.8 (5) | N1—C9—C11 | 105.9 (2) |
| F3'—C1'—F1'i | 158.3 (7) | O3—C10—N1 | 125.3 (3) |
| C2—C1'—F1'i | 89.4 (6) | O3—C10—C16 | 129.3 (3) |
| C1'i—C1'—F1'i | 44.8 (4) | N1—C10—C16 | 105.4 (3) |
| C1'—F1'—F2'i | 103.5 (6) | C12—C11—C16 | 121.7 (3) |
| C1'—F1'—C1'i | 60.8 (6) | C12—C11—C9 | 130.1 (3) |
| F2'i—F1'—C1'i | 47.0 (4) | C16—C11—C9 | 108.2 (3) |
| C1'—F2'—F1'i | 85.2 (6) | C11—C12—C13 | 117.2 (3) |
| C1'—C2—C1'i | 70.6 (8) | C11—C12—H12 | 121.4 |
| C1'—C2—C3 | 119.1 (3) | C13—C12—H12 | 121.4 |
| C1'i—C2—C3 | 114.6 (4) | C14—C13—C12 | 121.2 (3) |
| C1'—C2—C3i | 114.6 (4) | C14—C13—H13 | 119.4 |
| C1'i—C2—C3i | 119.1 (3) | C12—C13—H13 | 119.4 |
| C3—C2—C3i | 112.9 (4) | C15—C14—C13 | 121.1 (3) |
| C1'—C2—C1i | 99.4 (6) | C15—C14—H14 | 119.5 |
| C1'i—C2—C1i | 28.8 (4) | C13—C14—H14 | 119.5 |
| C3—C2—C1i | 100.9 (3) | C14—C15—C16 | 117.9 (3) |
| C3i—C2—C1i | 107.1 (3) | C14—C15—H15 | 121.0 |
| C1'—C2—C1 | 28.8 (4) | C16—C15—H15 | 121.0 |
| C1'i—C2—C1 | 99.4 (6) | C15—C16—C11 | 120.9 (3) |
| C3—C2—C1 | 107.1 (3) | C15—C16—C10 | 130.1 (3) |
| C3i—C2—C1 | 100.9 (3) | C11—C16—C10 | 108.9 (3) |
| C1i—C2—C1 | 128.2 (7) | C9—N1—C10 | 111.5 (2) |
| C4—C3—C5 | 118.4 (3) | C9—N1—C8 | 123.5 (2) |
| C4—C3—C2 | 122.7 (3) | C10—N1—C8 | 124.9 (2) |
| C5—C3—C2 | 118.8 (3) | ||
| F2'—C1'—F1'—F2'i | −103.3 (7) | C1'—C2—C3—C4 | −3.8 (6) |
| F3'—C1'—F1'—F2'i | 130.7 (8) | C1'i—C2—C3—C4 | 76.8 (6) |
| C2—C1'—F1'—F2'i | 19.4 (8) | C3i—C2—C3—C4 | −142.5 (4) |
| C1'i—C1'—F1'—F2'i | −20.2 (6) | C1i—C2—C3—C4 | 103.5 (5) |
| F1'i—C1'—F1'—F2'i | −65.8 (7) | C1—C2—C3—C4 | −32.4 (5) |
| F2'—C1'—F1'—C1'i | −83.2 (8) | C1'—C2—C3—C5 | −179.2 (5) |
| F3'—C1'—F1'—C1'i | 150.9 (8) | C1'i—C2—C3—C5 | −98.6 (6) |
| C2—C1'—F1'—C1'i | 39.6 (5) | C3i—C2—C3—C5 | 42.1 (3) |
| F1'i—C1'—F1'—C1'i | −45.6 (4) | C1i—C2—C3—C5 | −71.9 (5) |
| F1'—C1'—F2'—F1'i | 54.2 (8) | C1—C2—C3—C5 | 152.2 (4) |
| F3'—C1'—F2'—F1'i | −177.6 (8) | C5—C3—C4—C6 | −0.5 (6) |
| C2—C1'—F2'—F1'i | −70.8 (7) | C2—C3—C4—C6 | −175.9 (3) |
| C1'i—C1'—F2'—F1'i | −18.8 (5) | C4—C3—C5—C7 | −1.0 (6) |
| F1'—C1'—C2—C1'i | −48.7 (5) | C2—C3—C5—C7 | 174.6 (3) |
| F2'—C1'—C2—C1'i | 74.8 (7) | C3—C4—C6—C8 | 1.5 (5) |
| F3'—C1'—C2—C1'i | −170.0 (9) | C3—C5—C7—C8 | 1.5 (6) |
| F1'i—C1'—C2—C1'i | 30.4 (3) | C4—C6—C8—C7 | −0.9 (5) |
| F1'—C1'—C2—C3 | 59.2 (8) | C4—C6—C8—N1 | 179.5 (3) |
| F2'—C1'—C2—C3 | −177.2 (5) | C5—C7—C8—C6 | −0.5 (5) |
| F3'—C1'—C2—C3 | −62.0 (7) | C5—C7—C8—N1 | 179.0 (3) |
| C1'i—C1'—C2—C3 | 108.0 (5) | O1—C9—C11—C12 | −3.0 (6) |
| F1'i—C1'—C2—C3 | 138.4 (4) | N1—C9—C11—C12 | 178.6 (3) |
| F1'—C1'—C2—C3i | −162.7 (5) | O1—C9—C11—C16 | 177.2 (3) |
| F2'—C1'—C2—C3i | −39.1 (8) | N1—C9—C11—C16 | −1.2 (3) |
| F3'—C1'—C2—C3i | 76.1 (7) | C16—C11—C12—C13 | −1.0 (5) |
| C1'i—C1'—C2—C3i | −114.0 (5) | C9—C11—C12—C13 | 179.2 (3) |
| F1'i—C1'—C2—C3i | −83.5 (5) | C11—C12—C13—C14 | 0.5 (5) |
| F1'—C1'—C2—C1i | −48.9 (7) | C12—C13—C14—C15 | 0.2 (5) |
| F2'—C1'—C2—C1i | 74.7 (7) | C13—C14—C15—C16 | −0.4 (5) |
| F3'—C1'—C2—C1i | −170.1 (6) | C14—C15—C16—C11 | −0.2 (5) |
| C1'i—C1'—C2—C1i | −0.2 (6) | C14—C15—C16—C10 | 178.5 (3) |
| F1'i—C1'—C2—C1i | 30.3 (5) | C12—C11—C16—C15 | 0.9 (5) |
| F1'—C1'—C2—C1 | 130.9 (12) | C9—C11—C16—C15 | −179.2 (3) |
| F2'—C1'—C2—C1 | −105.5 (12) | C12—C11—C16—C10 | −178.0 (3) |
| F3'—C1'—C2—C1 | 9.7 (8) | C9—C11—C16—C10 | 1.8 (3) |
| C1'i—C1'—C2—C1 | 179.7 (12) | O3—C10—C16—C15 | −0.3 (6) |
| F1'i—C1'—C2—C1 | −149.9 (11) | N1—C10—C16—C15 | 179.4 (3) |
| F1—C1—C2—C1' | −42.3 (8) | O3—C10—C16—C11 | 178.6 (3) |
| F2—C1—C2—C1' | 75.0 (10) | N1—C10—C16—C11 | −1.7 (3) |
| F3—C1—C2—C1' | −165.7 (13) | O1—C9—N1—C10 | −178.4 (3) |
| F1—C1—C2—C1'i | −42.0 (7) | C11—C9—N1—C10 | 0.0 (3) |
| F2—C1—C2—C1'i | 75.3 (7) | O1—C9—N1—C8 | −2.0 (5) |
| F3—C1—C2—C1'i | −165.4 (6) | C11—C9—N1—C8 | 176.4 (3) |
| F1—C1—C2—C3 | 77.5 (7) | O3—C10—N1—C9 | −179.3 (3) |
| F2—C1—C2—C3 | −165.2 (5) | C16—C10—N1—C9 | 1.0 (3) |
| F3—C1—C2—C3 | −45.9 (7) | O3—C10—N1—C8 | 4.4 (5) |
| F1—C1—C2—C3i | −164.3 (5) | C16—C10—N1—C8 | −175.3 (3) |
| F2—C1—C2—C3i | −47.0 (7) | C6—C8—N1—C9 | −43.6 (4) |
| F3—C1—C2—C3i | 72.4 (6) | C7—C8—N1—C9 | 136.9 (3) |
| F1—C1—C2—C1i | −42.1 (5) | C6—C8—N1—C10 | 132.3 (3) |
| F2—C1—C2—C1i | 75.2 (6) | C7—C8—N1—C10 | −47.2 (4) |
| F3—C1—C2—C1i | −165.5 (7) |
| Symmetry codes: (i) −x+1/2, −y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C15—H15···O1ii | 0.93 | 2.42 | 3.199 (4) | 141 |
| Symmetry codes: (ii) x, −y+2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C15—H15···O1i | 0.93 | 2.42 | 3.199 (4) | 141 |
| Symmetry codes: (i) x, −y+2, z+1/2. |
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Bisimides are heterocyclic compounds that sometimes exhibit biological activity (Rich et al., 1975). Moreover, they are synthetic precursors with applications in organic synthesis (Degenhardt et al., 2002), polymer synthesis (Mallakpour & Kowsari, 2004), supramolecular chemistry (Zhang et al., 1999), and for the development of new materials (Langhals & Kirner, 2000) and molecular electronic devices (Yakimov & Forrest, 2002).
Following our studies on the synthesis of bisimides derivatives (Li et al., 2007), we report here the structure of the title compound (I), Fig. 1. In the molecule, two phthalimide units are linked by a (1,1-di-trifluoromethyl)-methylenedi-p-phenylene bridge. The dihedral angle between the planes of the two central benzene rings is 70.5 (3)°. The terminal isoindole group is approximately planar with a maximum r.m.s. deviation of 0.006Å from the best fit plane by C11 and makes a dihedral angle of 46.03 (3)° to the attached central benzene ring. Intermolecular C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).