2′-Iodo-2,2′′,3,3′′,4,4′′,5,5′′,6,6′′-deca­methyl-1,1′:3′,1′′-terphenyl chloro­form monosolvate

Marian Olaru; Sorin Roşca; Ciprian I Raţ

doi:10.1107/S1600536810052736

. 2010 Dec 24;67(Pt 1):o213. doi: 10.1107/S1600536810052736

2′-Iodo-2,2′′,3,3′′,4,4′′,5,5′′,6,6′′-decamethyl-1,1′:3′,1′′-terphenyl chloroform monosolvate

Marian Olaru ^a, Sorin Roşca ^a, Ciprian I Raţ ^a,^*

PMCID: PMC3050376 PMID: 21522713

Abstract

The title compound, C₂₈H₃₃I·CHCl₃, forms dimers through C—I⋯π interactions. The crystal structure is consolidated by the presence of C—H⋯π interactions between the chloroform solvent and the main molecule.

Related literature

For the synthesis and spectroscopic characterization of 2′-iodo-2,2′′,3,3′′,4,4′′,5,5′′,6,6′′-decamethyl-1,1′:3′,1′′-terphenyl, see: Hino et al. (2005 ▶); Duttwyler et al. (2008 ▶). For related m-terphenyl iodides, see: Niemeyer (1998 ▶); Twamley et al. (2000 ▶); Zakharov et al. (2003 ▶). For general background to compounds with m-terphenyl substituents, see: Power (2004 ▶).

Experimental

Crystal data

C₂₈H₃₃I·CHCl₃
M _r = 615.81
Monoclinic,
a = 12.0294 (10) Å
b = 16.0651 (13) Å
c = 15.3762 (12) Å
β = 103.385 (1)°
V = 2890.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.40 mm⁻¹
T = 297 K
0.32 × 0.28 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.663, T _max = 0.712
22910 measured reflections
5896 independent reflections
4698 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.137
S = 1.13
5896 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052736/pk2291sup1.cif

e-67-0o213-sup1.cif^{(24KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052736/pk2291Isup2.hkl

e-67-0o213-Isup2.hkl^{(282.8KB, hkl)}

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

Table 1. C—H⋯π interactions (Å, °).

Cg2 and C3 are the centroids of the C7–C12 and C18–C23 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26A⋯Cg2ⁱ	0.96	3.86 (1)	2.97	155
C28—H28A⋯Cg2ⁱⁱ	0.96	3.53 (1)	2.87	127
C29—H29⋯Cg3ⁱⁱⁱ	0.98	3.42 (1)	2.44	177

Open in a new tab

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

Table 2. C—I⋯π interactions (Å, °).

Cg3 is the centroid of the C18–C23 benzene ring.

Y—X⋯Cg	Y—X	X⋯Cg	Y⋯Cg	Y—X⋯Cg
C1—I1⋯Cg3ⁱ	2.099 (4)	3.975 (2)	6.026 (5)	164.67 (13)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National University Research Council (CNCSIS) of Romania (project TE 295/2010).

supplementary crystallographic information

Comment

m-Terphenyl substituents are sterrically crowded ligands used in stabilizing labile bonds and unusual geometries (Power, 2004).

We report herein the crystal structure of the title compound. The synthesis and the spectroscopic characterization of 2'-iodo-2,2'',3,3'',4,4'',5,5'',6,6''-decamethyl-1,1':3',1''-terphenyl were previously reported (Hino et al., 2005; Duttwyler et al., 2008).

The crystal structure (Fig. 1) of the title compound is similar to the structures of other 2,6-diarylphenyliodides. The C—I bond length [2.099 (4) Å] is slightly smaller than those found in 2,6-(2,4,6 - iPr₃C₆H₂)₂C₆H₃I [2.102 (6) Å] (Twamley et al., 2000), 2,6-Ph₂C₆H₃I [2.122 (4) Å] (Niemeyer, 1998), and 2,6-Mes₂C₆H₃I [2.102 (5) Å] (Zakharov et al., 2003).

Similar to the other 2,6-diarylphenyliodides, the dihedral angles between the flanking groups and the central benzene ring are close to 90° (Niemeyer, 1998; Twamley et al., 2000; Zakharov et al., 2003). This arrangement permits the presence of an intramolecular I···Cg contact [3.955 (1) Å]. The I···Cg interaction is reflected in the difference [Δ = 2.9°] at the C1 bonding angles.

In the crystal structure symmetry related molecules are linked into dimers through C—I···π interactions (Table 1 and Fig. 2). In addition there are C—H···π interactions (Table 2 and Fig. 2) that link the dimeric units and the solvent molecules into a three dimensional network.

Experimental

The synthesis of 2'-iodo-2,2'',3,3'',4,4'',5,5'',6,6''-decamethyl-1,1':3',1''-terphenyl was carried out according to a previously described method (Hino et al., 2005). Crystals of the title compound were obtained by slow evaporation of the solvent from a solution of 2'-iodo-2,2'',3,3'',4,4'',5,5'',6,6''-decamethyl-1,1':3',1''-terphenyl in chloroform.