4,6,10,12,16,18,22,24-Octa-O-methyl-2,8,14,20-tetra­pentylresorcin[4]arene

Pramod B Pansuriya; Holger B Friedrich; Glenn E M Maguire

doi:10.1107/S1600536811034003

. 2011 Sep 14;67(Pt 10):o2565. doi: 10.1107/S1600536811034003

4,6,10,12,16,18,22,24-Octa-O-methyl-2,8,14,20-tetrapentylresorcin[4]arene

Pramod B Pansuriya ^a, Holger B Friedrich ^a, Glenn E M Maguire ^a,^*

PMCID: PMC3201257 PMID: 22058735

Abstract

The complete molecule of the title compound, C₅₆H₈₀O₈, is generated by a crystallographic inversion centre. The dihedral angle between the aromatic ring and the unique half of the molecule is 81.52 (16)°. There are no π–π interactions in the crystal structure.

Related literature

For literature related to applications of resorcin[4]arenes, see: Gibson & Rebek (2002 ▶); Kim et al. (2005 ▶); Liu et al. (2010 ▶); D’Acquarica et al. (2011 ▶). For related structures, see: Botta et al. (2007 ▶); Iwanek (1998 ▶); Davis et al. (2001 ▶); Gerkensmeier et al. (2001 ▶); Moore & Matthews (2009 ▶).

Experimental

Crystal data

C₅₆H₈₀O₈
M _r = 881.20
Triclinic,
a = 8.2084 (2) Å
b = 14.1270 (2) Å
c = 23.1489 (4) Å
α = 98.929 (1)°
β = 97.914 (1)°
γ = 103.581 (1)°
V = 2534.93 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.44 × 0.39 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
42741 measured reflections
12226 independent reflections
7816 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.148
S = 0.99
12226 reflections
589 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034003/hg5082sup1.cif

e-67-o2565-sup1.cif^{(39.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034003/hg5082Isup2.hkl

e-67-o2565-Isup2.hkl^{(585.7KB, hkl)}

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

Acknowledgments

The authors thank Dr Manuel Fernandes from the University of the Witwatersrand for his assistance with the data collection and refinement.

supplementary crystallographic information

Comment

Resorcin[4]arenes are easily prepared macromolecules that are used for a range of applications in supramolecular chemistry such as catalysis (Gibson & Rebek, 2002), self-assembled nanoparticles (Kim et al., 2005), molecular recognition (Liu et al., 2010) and noncompetitive inhibitors for R-chymotrypsin (D'Acquarica et al., 2011).

The different conformers of resorcin[4]arenes that can occur in solution have been extensively reported (Moore & Matthews, 2009). Their topology has been classified into four diffrent structures i.e. rccc (cone/crown), rctt (chair), rctc (diamond), rccc (boat). The most commonly reported single-crystal X-ray structures have been the crown and boat isomers (Davis et al., 2001; Gerkensmeier et al., 2001). In the title compound, a pair of aromatic rings are almost coplanar (C8—C9—C11—C12—C13), whereas the others are orthogonal at an angle of 86.91° from the plane facing the side-chains. This creates an rctt conformation (Fig 1). Botta et al. have described the only other rctt octamethoxy-resorcin[4]arene structure thus far (Botta et al., 2007) which had ethyl ester side chains. Iwanek have reported the only rctc octamethoxy resorcinarene (Iwanek, 1998) with isopropyl side chains. There are no π–π interactions in the crystal matrix (Fig. 2).

Experimental

1,3-Dimethoxybenzene (1.054 g, 7.63 mmol) and hexanal (0.764 g, 7.63 mmol) were added to diethyl ether (20 ml) followed by addition of thionyl chloride (0.907 g, 7.63 mmol). The solution was stirred at room temperature for 24 h. Subsequently, methanol (40 ml) was added, and the mixture was stirred for 1 h. The resulting precipitate was collected by filtration and washed with methanol. The yield was 0.65 g (36%). m.p. = 516–519 K.

Crystals suitable for single-crystal X-ray diffraction were grown in methanol: methylene chloride (1:2) at room temperature.