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

Yitao Li; Zhiguo Wang

doi:10.1107/S1600536807068249

. 2008 Jan 9;64(Pt 2):o388. doi: 10.1107/S1600536807068249

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

Yitao Li ^a,^*, Zhiguo Wang ^b

PMCID: PMC2960178 PMID: 21201418

Abstract

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.

Related literature

For details of the biological activity and uses of bis(imide) derivatives, see: Rich et al. (1975 ▶); Degenhardt et al. (2002 ▶); Mallakpour & Kowsari (2004 ▶); Zhang et al. (1999 ▶); Langhals & Kirner (2000 ▶); Yakimov & Forrest (2002 ▶). For a related structure, see: Li et al. (2007 ▶).

Experimental

Crystal data

C₃₁H₁₆F₆N₂O₄
M _r = 594.46
Orthorhombic,
a = 13.3588 (19) Å
b = 12.5340 (18) Å
c = 15.792 (2) Å
V = 2644.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 292 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
15610 measured reflections
2607 independent reflections
1864 reflections with I > 2σ(I)
R _int = 0.119

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.168
S = 1.05
2607 reflections
232 parameters
64 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068249/ez2112sup1.cif

e-64-0o388-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068249/ez2112Isup2.hkl

e-64-0o388-Isup2.hkl^{(128.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1ⁱ	0.93	2.42	3.199 (4)	141

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Xiang-Gao Meng for the X-ray data collection.

supplementary crystallographic information

Comment

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).

Experimental

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.