N,N′-(Oxydi-p-phenyl­ene)diphthalimide

Yi-Tao Li; Zhiguo Wang

doi:10.1107/S1600536807057455

. 2007 Dec 6;64(Pt 1):o77. doi: 10.1107/S1600536807057455

N,N′-(Oxydi-p-phenylene)diphthalimide

Yi-Tao Li ^a,^*, Zhiguo Wang ^b

PMCID: PMC2915034 PMID: 21200954

Abstract

The title compound, C₂₈H₁₆N₂O₅, is a bis-imide derivative in which two phthalimide units are linked by an oxydi-p-phenylene bridge. The dihedral angle between the planes of the two central benzene rings is 86.1 (4)°. The isoindole groups make dihedral angles of 46.0 (14) and 77.5 (13)° with the attached benzene rings. Intermolecular C—H⋯O hydrogen bonds contribute to the stability of the structure.

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

C₂₈H₁₆N₂O₅
M _r = 460.43
Orthorhombic,
a = 7.5059 (11) Å
b = 16.480 (3) Å
c = 17.551 (3) Å
V = 2171.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 292 (2) K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
13091 measured reflections
2925 independent reflections
2644 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.118
S = 1.23
2925 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807057455/wn2220sup1.cif

e-64-00o77-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807057455/wn2220Isup2.hkl

e-64-00o77-Isup2.hkl^{(143.6KB, 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
C11—H11⋯O5ⁱ	0.93	2.47	3.222 (4)	138
C19—H19⋯O5ⁱⁱ	0.93	2.56	3.298 (4)	136

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Bisimides are heterocyclic compounds, some of which have 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 bisimide derivatives (Li et al., 2007), we report here the structure of the title compound (Fig. 1). The two phthalimide units are linked by a (phenoxy)phenylene bridge. The dihedral angle between the planes of the two central benzene rings is 86.1 (4)° The isoindole groups make dihedral angles of 46.0 (14)° and 77.5 (13)° with the attached benzene rings. Compared to a similar structure, N,N'-(methylenedi-p-phenylene)diphthalimide (Li et al., 2007), the packing pattern is different; this may be due to the bridging methylene group being replaced by the bridging O atom. 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-aminophenyl ether (400 mg, 2 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 (yield 510 mg, 70%). Single crystals of the title compound were obtained by recrystallization from dimethylformamide at room temperature.