2,2′-(3,3′-Dihexyl-2,2′-bithio­phene-5,5′-di­yl)bis­(4,4,5,5-tetra­methyl-1,3,2-dioxaborolane)

Lin Huang; Huisheng Li

doi:10.1107/S1600536811050938

. 2011 Nov 30;67(Pt 12):o3512. doi: 10.1107/S1600536811050938

2,2′-(3,3′-Dihexyl-2,2′-bithiophene-5,5′-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Lin Huang ^a,^*, Huisheng Li ^a

PMCID: PMC3239133 PMID: 22199981

Abstract

In the title molecule, C₃₂H₅₂B₂O₄S₂, the two thiophene rings are twisted by 67.34 (2)°. In the crystal, weak C—H⋯O hydrogen bonds link molecules related by translation along the a axis into chains.

Related literature

For potential applications of the title compound, see: Navarro et al. (2004 ▶); Usta et al. (2006 ▶); Buszek & Brown (2007 ▶); Montes et al. (2007 ▶). For related structures, see: Decken et al. (2008 ▶); Kleeberg et al. (2009 ▶).

Experimental

Crystal data

C₃₂H₅₂B₂O₄S₂
M _r = 586.48
Monoclinic,
a = 11.5004 (11) Å
b = 13.6992 (13) Å
c = 21.300 (2) Å
β = 91.065 (2)°
V = 3355.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.970, T _max = 0.981
29998 measured reflections
9743 independent reflections
8009 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.118
S = 1.05
9743 reflections
371 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050938/cv5202sup1.cif

e-67-o3512-sup1.cif^{(29.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050938/cv5202Isup2.hkl

e-67-o3512-Isup2.hkl^{(476.5KB, 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
C30—H30C⋯O1ⁱ	0.98	2.53	3.2984 (18)	136

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to Xiangfan University for financial support.

supplementary crystallographic information

Comment

Arylboronic acid and their esters are important reactants in the Suzuki-Miyaura cross-coupling reactions (Navarro et al., 2004; Buszek et al., 2007). Lots of functional organic compounds which have broad applications in material chemistry are prepared via the named reaction (Montes et al., 2007; Usta et al., 2006). We herein report the crystal structure of the title compound (I).

In (I) (Fig. 1), the geometric parameters of 2-(thiophene-2-yl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane fragments are normal and comparable with those observed in related structures (Decken et al., 2008; Kleeberg et al., 2009). Two thiophene rings are twisted at 67.34 (2)°. In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules related by translation along axis a into chains.

Experimental

The powder form of the title compound (I) was purchased from Aldrich chemical company. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a acetone and MeOH solution in a ratio of 1:2 at room temperature for several days.