N,N′-{[Bis(trifluoromethyl)methylene]di-p-phenylene}diphthalimide

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.

The molecule of the title compound, C 31 H 16 F 6 N 2 O 4 , 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-HÁ Á ÁO hydrogen bonds link neighboring molecules into chains along the c axis.
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-pphenylene 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).

S3. Refinement
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 U iso (H)=1.2U eq (C) for aromatic H atoms.  The molecular structure of (I) showing atom labels with 50% probability displacement ellipsoids.

N,N′-{[Bis(trifluoromethyl)methylene]di-p-phenylene}diphthalimide
Crystal data  Special details 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 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 )