1,1,1,3,3,3-Hexafluoro-2,2-bis­[4-(4-nitro­phen­oxy)phen­yl]propane

H Nawaz; Zareen Akhter; Michael Bolte; M S Butt; Humaira M Siddiqi

doi:10.1107/S1600536808022101

. 2008 Jul 19;64(Pt 8):o1537. doi: 10.1107/S1600536808022101

1,1,1,3,3,3-Hexafluoro-2,2-bis[4-(4-nitrophenoxy)phenyl]propane

H Nawaz ^a, Zareen Akhter ^a,^*, Michael Bolte ^b, M S Butt ^a, Humaira M Siddiqi ^a

PMCID: PMC2962162 PMID: 21203242

Abstract

In the title compound, C₂₇H₁₆F₆N₂O₆, the nitro groups are almost coplanar with the aromatic rings to which they are attached [dihedral angles = 3.5 (5) and 6.2 (3)°]. The dihedral angles between adjacent aromatic rings are 78.07 (8) and 71.11 (8)° for nitrophenyl/phenyl and 69.50 (8)° for phenyl/phenyl. An intermolecular C—H⋯π interaction seems to be effective in the stabilization of the structure.

Related literature

For related literature, see: Liaw et al. (2005 ▶); Yang et al. (2003 ▶); Miyagawa et al. (2003 ▶); Leu et al. (2003 ▶); Zhou et al. (2001 ▶.

Experimental

Crystal data

C₂₇H₁₆F₆N₂O₆
M _r = 578.42
Monoclinic,
a = 25.523 (3) Å
b = 10.5530 (12) Å
c = 9.3869 (8) Å
β = 98.248 (8)°
V = 2502.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 173 (2) K
0.23 × 0.10 × 0.10 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: none
13020 measured reflections
4653 independent reflections
2651 reflections with I > 2σ(I)
R _int = 0.076

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.092
S = 0.91
4653 reflections
371 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022101/bq2089sup1.cif

e-64-o1537-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022101/bq2089Isup2.hkl

e-64-o1537-Isup2.hkl^{(228KB, 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
C46—H46⋯Cg1ⁱ	0.95	3.04	3.710	129

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Symmetry code: (i) Inline graphic . Cg1 is the centroid of the C31–C36 ring.

Acknowledgments

The authors are grateful to the Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan, and to the Institute for Inorganic Chemistry, University of Frankfurt, Germany, for providing laboratory and analytical facilities.

supplementary crystallographic information

Comment

Aromatic polyimides have many useful properties, such as high glass transition temperature, excellent dimensional stability, low dielectric constant and outstanding thermal stability (Liaw et al. 2005). Polyimides also have many commercial applications but one of the problems with the polyimides is their poor solubility (Yang et al. 2003). Many efforts have been made to increase the solubility (Miyagawa et al. 2003) and processability of the polyimides. The common strategy that enhances the solubility is the introduction of flexible linkages, bulky substituents (Leu et al. 2003) and structurally unsymmetrical segment (Zhou et al. 2001) in to the polymer backbone. The present compound is the starting material for such types of polymers.

Geometric parameters of (I) are in the usual ranges. The nitro groups are almost coplanar with the aromatic rings to which they are attached [dihedral angles: 3.5 (5)128.52 and 6.2 (3)°], (Figure 1.). The dihedral angles between the adjacent aromatic rings are 78.07 (8)° and 71.11 (8)° for nitrophenyl/phenyl and 69.50 (8)° for phenyl/phenyl. The C46···H46-Cg1 intermolecular interaction seems to be effective in the stabilization of the structure. Cg1 is the center of the ring (C31-C36) at the symmetry of x, 1/2-y, 1/2+z (Table 1.)

Experimental

A mixture containing 2 g (5.94 mmol) of 4,4'-(hexafluoroisopropylidene)-diphenol, 2.25 g (11.88 mmol) of anhydrous potassium carbonate, and 1.87 g (11.88 mmoles) of p-nitrochlorobenzene, in 70 mL of DMF was heated at 120° C for 18 h in nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into 500 mL of water to form precipitates and washed thoroughly with water and then collected by filtration. The crude product was recrystallized from ethanol. m.p.352 K.