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

Huang, L.; Li, H.

doi:10.1107/S1600536811050938

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3512

https://doi.org/10.1107/S1600536811050938

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

Lin Huang ^a ^* and Huisheng Li ^a

^aDepartment of Chemistry and Biology, Xiangfan University, Xiangfan 441053, People's Republic of China
^*Correspondence e-mail: hlwork02@126.com

(Received 12 November 2011; accepted 27 November 2011; online 30 November 2011)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 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

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
Symmetry code: (i) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050938/cv5202sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050938/cv5202Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

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

Crystal data top

C₃₂H₅₂B₂O₄S₂	F(000) = 1272
M_r = 586.48	D_x = 1.161 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9936 reflections
a = 11.5004 (11) Å	θ = 2.3–31.9°
b = 13.6992 (13) Å	µ = 0.19 mm⁻¹
c = 21.300 (2) Å	T = 100 K
β = 91.065 (2)°	Block, yellow
V = 3355.1 (6) Å³	0.16 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	9743 independent reflections
Radiation source: fine-focus sealed tube	8009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→9
T_min = 0.970, T_max = 0.981	k = −19→19
29998 measured reflections	l = −29→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0667P)² + 1.0083P] where P = (F_o² + 2F_c²)/3
9743 reflections	(Δ/σ)_max = 0.002
371 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₃₂H₅₂B₂O₄S₂	V = 3355.1 (6) Å³
M_r = 586.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5004 (11) Å	µ = 0.19 mm⁻¹
b = 13.6992 (13) Å	T = 100 K
c = 21.300 (2) Å	0.16 × 0.12 × 0.10 mm
β = 91.065 (2)°

Data collection top

Bruker APEX CCD diffractometer	9743 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	8009 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.981	R_int = 0.026
29998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	Δρ_max = 0.56 e Å⁻³
9743 reflections	Δρ_min = −0.27 e Å⁻³
371 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	1.10475 (12)	0.42742 (10)	0.66320 (6)	0.0165 (2)
B2	0.42238 (12)	0.75653 (10)	0.66220 (6)	0.0177 (2)
C1	1.31526 (14)	0.45484 (11)	0.78413 (7)	0.0302 (3)
H1A	1.3426	0.5109	0.7599	0.045*
H1B	1.3818	0.4142	0.7968	0.045*
H1C	1.2756	0.4781	0.8216	0.045*
C2	1.23132 (11)	0.39499 (9)	0.74398 (6)	0.0191 (2)
C3	1.17597 (13)	0.31513 (11)	0.78332 (6)	0.0252 (3)
H3A	1.1323	0.3449	0.8174	0.038*
H3B	1.2369	0.2728	0.8011	0.038*
H3C	1.1231	0.2763	0.7568	0.038*
C4	1.37052 (12)	0.42478 (12)	0.65253 (7)	0.0292 (3)
H4A	1.3879	0.4033	0.6098	0.044*
H4B	1.4418	0.4234	0.6784	0.044*
H4C	1.3396	0.4914	0.6512	0.044*
C5	1.28072 (11)	0.35677 (9)	0.68070 (6)	0.0181 (2)
C6	1.32667 (12)	0.25288 (10)	0.68271 (6)	0.0245 (3)
H6A	1.2653	0.2088	0.6968	0.037*
H6B	1.3933	0.2492	0.7120	0.037*
H6C	1.3511	0.2335	0.6407	0.037*
C7	0.99473 (10)	0.46694 (8)	0.62913 (5)	0.0160 (2)
C8	0.94547 (11)	0.44202 (9)	0.57185 (6)	0.0167 (2)
H8	0.9786	0.3946	0.5450	0.020*
C9	0.84128 (10)	0.49275 (8)	0.55611 (5)	0.0152 (2)
C10	0.81274 (10)	0.55846 (8)	0.60262 (5)	0.0140 (2)
C11	0.76632 (12)	0.47441 (9)	0.49844 (6)	0.0205 (2)
H11A	0.8136	0.4423	0.4660	0.025*
H11B	0.7386	0.5376	0.4813	0.025*
C12	0.66060 (12)	0.40942 (10)	0.51308 (7)	0.0245 (3)
H12A	0.6217	0.4358	0.5505	0.029*
H12B	0.6045	0.4129	0.4773	0.029*
C13	0.69119 (12)	0.30299 (10)	0.52511 (7)	0.0255 (3)
H13A	0.7580	0.3000	0.5550	0.031*
H13B	0.7159	0.2730	0.4852	0.031*
C14	0.59126 (13)	0.24350 (10)	0.55138 (7)	0.0266 (3)
H14A	0.5805	0.2622	0.5958	0.032*
H14B	0.5189	0.2604	0.5279	0.032*
C15	0.60942 (14)	0.13357 (11)	0.54790 (8)	0.0321 (3)
H15A	0.6157	0.1142	0.5033	0.038*
H15B	0.6838	0.1169	0.5694	0.038*
C16	0.51228 (16)	0.07546 (12)	0.57741 (9)	0.0380 (4)
H16A	0.5080	0.0918	0.6221	0.057*
H16B	0.5279	0.0055	0.5728	0.057*
H16C	0.4382	0.0915	0.5564	0.057*
C17	0.71460 (10)	0.62709 (8)	0.60397 (5)	0.0142 (2)
C18	0.69640 (10)	0.70849 (8)	0.56718 (5)	0.0159 (2)
C19	0.59343 (11)	0.75836 (9)	0.58463 (6)	0.0175 (2)
H19	0.5672	0.8160	0.5640	0.021*
C20	0.53489 (10)	0.71694 (9)	0.63341 (6)	0.0173 (2)
C21	0.77521 (12)	0.74408 (9)	0.51653 (6)	0.0201 (2)
H21A	0.7327	0.7420	0.4757	0.024*
H21B	0.8428	0.6996	0.5138	0.024*
C22	0.81873 (15)	0.84760 (10)	0.52837 (7)	0.0290 (3)
H22A	0.8755	0.8465	0.5639	0.035*
H22B	0.7523	0.8888	0.5409	0.035*
C23	0.87603 (13)	0.89414 (10)	0.47171 (7)	0.0256 (3)
H23A	0.8210	0.8912	0.4355	0.031*
H23B	0.8911	0.9638	0.4811	0.031*
C24	0.98960 (13)	0.84615 (11)	0.45327 (7)	0.0285 (3)
H24A	0.9740	0.7773	0.4417	0.034*
H24B	1.0435	0.8461	0.4901	0.034*
C25	1.04875 (13)	0.89695 (11)	0.39843 (7)	0.0277 (3)
H25A	1.0532	0.9679	0.4071	0.033*
H25B	1.1293	0.8721	0.3953	0.033*
C26	0.98547 (14)	0.88121 (11)	0.33606 (7)	0.0297 (3)
H26A	0.9815	0.8112	0.3269	0.045*
H26B	1.0275	0.9145	0.3027	0.045*
H26C	0.9065	0.9078	0.3383	0.045*
C27	0.26538 (12)	0.77376 (10)	0.72424 (7)	0.0228 (3)
C28	0.26948 (11)	0.85917 (9)	0.67599 (6)	0.0197 (2)
C29	0.24609 (16)	0.80293 (14)	0.79156 (8)	0.0398 (4)
H29A	0.2499	0.7449	0.8184	0.060*
H29B	0.1694	0.8335	0.7950	0.060*
H29C	0.3064	0.8494	0.8050	0.060*
C30	0.17912 (14)	0.69466 (11)	0.70388 (10)	0.0402 (4)
H30A	0.1920	0.6774	0.6599	0.060*
H30B	0.0996	0.7190	0.7084	0.060*
H30C	0.1904	0.6367	0.7303	0.060*
C31	0.15711 (14)	0.87827 (12)	0.64025 (8)	0.0343 (3)
H31A	0.1682	0.9321	0.6107	0.051*
H31B	0.0962	0.8956	0.6698	0.051*
H31C	0.1340	0.8194	0.6170	0.051*
C32	0.31596 (14)	0.95370 (11)	0.70410 (8)	0.0326 (3)
H32A	0.3881	0.9404	0.7278	0.049*
H32B	0.2582	0.9814	0.7323	0.049*
H32C	0.3316	1.0002	0.6703	0.049*
O1	1.13638 (8)	0.45839 (7)	0.72232 (4)	0.02101 (19)
O2	1.17824 (8)	0.35991 (7)	0.63862 (4)	0.01828 (17)
O3	0.38074 (8)	0.72931 (7)	0.71924 (5)	0.0244 (2)
O4	0.35654 (8)	0.82553 (7)	0.63193 (4)	0.02210 (19)
S1	0.91171 (3)	0.55548 (2)	0.664168 (13)	0.01627 (7)
S2	0.60692 (3)	0.61359 (2)	0.658712 (14)	0.01632 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0150 (6)	0.0170 (6)	0.0175 (6)	0.0001 (4)	−0.0012 (5)	0.0024 (4)
B2	0.0148 (6)	0.0190 (6)	0.0193 (6)	0.0010 (5)	−0.0016 (5)	−0.0020 (5)
C1	0.0296 (7)	0.0292 (7)	0.0313 (7)	0.0020 (6)	−0.0147 (6)	−0.0049 (6)
C2	0.0177 (6)	0.0207 (5)	0.0188 (5)	0.0035 (4)	−0.0051 (4)	0.0003 (4)
C3	0.0247 (7)	0.0314 (7)	0.0195 (6)	0.0033 (5)	0.0000 (5)	0.0052 (5)
C4	0.0174 (6)	0.0360 (7)	0.0341 (7)	−0.0024 (5)	−0.0016 (5)	0.0115 (6)
C5	0.0137 (5)	0.0219 (5)	0.0186 (5)	0.0025 (4)	−0.0029 (4)	0.0029 (4)
C6	0.0224 (6)	0.0256 (6)	0.0254 (6)	0.0085 (5)	−0.0020 (5)	0.0009 (5)
C7	0.0135 (5)	0.0174 (5)	0.0171 (5)	0.0020 (4)	−0.0002 (4)	0.0009 (4)
C8	0.0160 (5)	0.0173 (5)	0.0169 (5)	0.0024 (4)	0.0013 (4)	0.0002 (4)
C9	0.0151 (5)	0.0155 (5)	0.0148 (5)	0.0001 (4)	−0.0010 (4)	0.0005 (4)
C10	0.0124 (5)	0.0150 (5)	0.0146 (5)	−0.0003 (4)	−0.0006 (4)	0.0009 (4)
C11	0.0240 (6)	0.0213 (5)	0.0159 (5)	0.0017 (5)	−0.0047 (4)	−0.0016 (4)
C12	0.0218 (6)	0.0249 (6)	0.0263 (6)	0.0005 (5)	−0.0074 (5)	−0.0040 (5)
C13	0.0241 (7)	0.0259 (6)	0.0263 (6)	−0.0023 (5)	−0.0026 (5)	−0.0022 (5)
C14	0.0244 (7)	0.0275 (6)	0.0277 (7)	−0.0027 (5)	−0.0052 (5)	−0.0028 (5)
C15	0.0267 (7)	0.0267 (7)	0.0427 (8)	−0.0018 (6)	−0.0028 (6)	−0.0002 (6)
C16	0.0362 (9)	0.0270 (7)	0.0508 (10)	−0.0042 (6)	−0.0023 (7)	0.0037 (7)
C17	0.0125 (5)	0.0160 (5)	0.0143 (5)	−0.0002 (4)	0.0001 (4)	−0.0011 (4)
C18	0.0162 (5)	0.0164 (5)	0.0151 (5)	0.0016 (4)	0.0004 (4)	−0.0003 (4)
C19	0.0181 (6)	0.0167 (5)	0.0178 (5)	0.0040 (4)	−0.0015 (4)	−0.0003 (4)
C20	0.0151 (5)	0.0182 (5)	0.0185 (5)	0.0019 (4)	−0.0014 (4)	−0.0017 (4)
C21	0.0242 (6)	0.0175 (5)	0.0189 (5)	0.0016 (5)	0.0049 (5)	0.0016 (4)
C22	0.0424 (9)	0.0217 (6)	0.0232 (6)	−0.0055 (6)	0.0115 (6)	−0.0010 (5)
C23	0.0335 (8)	0.0196 (6)	0.0241 (6)	0.0004 (5)	0.0076 (5)	0.0039 (5)
C24	0.0293 (7)	0.0315 (7)	0.0248 (6)	0.0027 (6)	0.0009 (5)	0.0078 (5)
C25	0.0238 (7)	0.0341 (7)	0.0252 (7)	−0.0029 (5)	0.0022 (5)	0.0031 (5)
C26	0.0304 (8)	0.0345 (7)	0.0245 (7)	−0.0019 (6)	0.0052 (6)	−0.0020 (5)
C27	0.0176 (6)	0.0220 (6)	0.0291 (6)	0.0064 (5)	0.0063 (5)	0.0062 (5)
C28	0.0164 (6)	0.0199 (5)	0.0228 (6)	0.0041 (4)	0.0038 (4)	0.0009 (4)
C29	0.0375 (9)	0.0540 (10)	0.0284 (7)	0.0162 (8)	0.0117 (6)	0.0098 (7)
C30	0.0246 (7)	0.0231 (7)	0.0732 (12)	−0.0018 (6)	0.0112 (8)	0.0030 (7)
C31	0.0265 (7)	0.0380 (8)	0.0382 (8)	0.0115 (6)	−0.0042 (6)	0.0049 (6)
C32	0.0288 (8)	0.0230 (6)	0.0464 (9)	−0.0026 (6)	0.0106 (7)	−0.0076 (6)
O1	0.0206 (4)	0.0220 (4)	0.0202 (4)	0.0071 (3)	−0.0061 (3)	−0.0023 (3)
O2	0.0148 (4)	0.0229 (4)	0.0171 (4)	0.0036 (3)	−0.0029 (3)	0.0000 (3)
O3	0.0172 (4)	0.0299 (5)	0.0261 (5)	0.0092 (4)	0.0052 (4)	0.0081 (4)
O4	0.0223 (5)	0.0248 (4)	0.0193 (4)	0.0089 (4)	0.0043 (3)	0.0022 (3)
S1	0.01508 (14)	0.01852 (14)	0.01509 (13)	0.00182 (10)	−0.00279 (10)	−0.00195 (10)
S2	0.01368 (14)	0.01725 (13)	0.01810 (14)	0.00051 (10)	0.00189 (10)	0.00161 (10)

Geometric parameters (Å, º) top

B1—O2	1.3638 (16)	C16—H16A	0.9800
B1—O1	1.3715 (16)	C16—H16B	0.9800
B1—C7	1.5449 (18)	C16—H16C	0.9800
B2—O4	1.3654 (16)	C17—C18	1.3767 (16)
B2—O3	1.3660 (17)	C17—S2	1.7265 (12)
B2—C20	1.5408 (18)	C18—C19	1.4225 (16)
C1—C2	1.5181 (18)	C18—C21	1.5030 (17)
C1—H1A	0.9800	C19—C20	1.3715 (17)
C1—H1B	0.9800	C19—H19	0.9500
C1—H1C	0.9800	C20—S2	1.7218 (12)
C2—O1	1.4631 (14)	C21—C22	1.5233 (18)
C2—C3	1.5244 (19)	C21—H21A	0.9900
C2—C5	1.5627 (18)	C21—H21B	0.9900
C3—H3A	0.9800	C22—C23	1.5254 (19)
C3—H3B	0.9800	C22—H22A	0.9900
C3—H3C	0.9800	C22—H22B	0.9900
C4—C5	1.5223 (18)	C23—C24	1.520 (2)
C4—H4A	0.9800	C23—H23A	0.9900
C4—H4B	0.9800	C23—H23B	0.9900
C4—H4C	0.9800	C24—C25	1.5301 (19)
C5—O2	1.4681 (14)	C24—H24A	0.9900
C5—C6	1.5184 (18)	C24—H24B	0.9900
C6—H6A	0.9800	C25—C26	1.518 (2)
C6—H6B	0.9800	C25—H25A	0.9900
C6—H6C	0.9800	C25—H25B	0.9900
C7—C8	1.3785 (16)	C26—H26A	0.9800
C7—S1	1.7223 (12)	C26—H26B	0.9800
C8—C9	1.4199 (16)	C26—H26C	0.9800
C8—H8	0.9500	C27—O3	1.4654 (15)
C9—C10	1.3826 (16)	C27—C29	1.509 (2)
C9—C11	1.5086 (16)	C27—C30	1.526 (2)
C10—C17	1.4696 (16)	C27—C28	1.5587 (18)
C10—S1	1.7206 (12)	C28—O4	1.4598 (15)
C11—C12	1.5434 (19)	C28—C31	1.510 (2)
C11—H11A	0.9900	C28—C32	1.5196 (19)
C11—H11B	0.9900	C29—H29A	0.9800
C12—C13	1.5204 (19)	C29—H29B	0.9800
C12—H12A	0.9900	C29—H29C	0.9800
C12—H12B	0.9900	C30—H30A	0.9800
C13—C14	1.524 (2)	C30—H30B	0.9800
C13—H13A	0.9900	C30—H30C	0.9800
C13—H13B	0.9900	C31—H31A	0.9800
C14—C15	1.522 (2)	C31—H31B	0.9800
C14—H14A	0.9900	C31—H31C	0.9800
C14—H14B	0.9900	C32—H32A	0.9800
C15—C16	1.518 (2)	C32—H32B	0.9800
C15—H15A	0.9900	C32—H32C	0.9800
C15—H15B	0.9900

O2—B1—O1	114.00 (11)	C18—C17—C10	128.00 (11)
O2—B1—C7	124.42 (11)	C18—C17—S2	111.58 (9)
O1—B1—C7	121.59 (11)	C10—C17—S2	120.36 (8)
O4—B2—O3	114.12 (11)	C17—C18—C19	111.02 (11)
O4—B2—C20	121.21 (11)	C17—C18—C21	125.73 (11)
O3—B2—C20	124.66 (11)	C19—C18—C21	123.22 (10)
C2—C1—H1A	109.5	C20—C19—C18	114.97 (11)
C2—C1—H1B	109.5	C20—C19—H19	122.5
H1A—C1—H1B	109.5	C18—C19—H19	122.5
C2—C1—H1C	109.5	C19—C20—B2	125.70 (11)
H1A—C1—H1C	109.5	C19—C20—S2	109.71 (9)
H1B—C1—H1C	109.5	B2—C20—S2	124.59 (9)
O1—C2—C1	108.66 (10)	C18—C21—C22	112.57 (10)
O1—C2—C3	106.41 (11)	C18—C21—H21A	109.1
C1—C2—C3	110.22 (11)	C22—C21—H21A	109.1
O1—C2—C5	102.00 (9)	C18—C21—H21B	109.1
C1—C2—C5	115.42 (12)	C22—C21—H21B	109.1
C3—C2—C5	113.32 (11)	H21A—C21—H21B	107.8
C2—C3—H3A	109.5	C21—C22—C23	113.81 (11)
C2—C3—H3B	109.5	C21—C22—H22A	108.8
H3A—C3—H3B	109.5	C23—C22—H22A	108.8
C2—C3—H3C	109.5	C21—C22—H22B	108.8
H3A—C3—H3C	109.5	C23—C22—H22B	108.8
H3B—C3—H3C	109.5	H22A—C22—H22B	107.7
C5—C4—H4A	109.5	C24—C23—C22	114.17 (12)
C5—C4—H4B	109.5	C24—C23—H23A	108.7
H4A—C4—H4B	109.5	C22—C23—H23A	108.7
C5—C4—H4C	109.5	C24—C23—H23B	108.7
H4A—C4—H4C	109.5	C22—C23—H23B	108.7
H4B—C4—H4C	109.5	H23A—C23—H23B	107.6
O2—C5—C6	108.64 (10)	C23—C24—C25	113.38 (12)
O2—C5—C4	106.51 (10)	C23—C24—H24A	108.9
C6—C5—C4	110.27 (11)	C25—C24—H24A	108.9
O2—C5—C2	102.49 (9)	C23—C24—H24B	108.9
C6—C5—C2	114.94 (10)	C25—C24—H24B	108.9
C4—C5—C2	113.27 (11)	H24A—C24—H24B	107.7
C5—C6—H6A	109.5	C26—C25—C24	113.00 (12)
C5—C6—H6B	109.5	C26—C25—H25A	109.0
H6A—C6—H6B	109.5	C24—C25—H25A	109.0
C5—C6—H6C	109.5	C26—C25—H25B	109.0
H6A—C6—H6C	109.5	C24—C25—H25B	109.0
H6B—C6—H6C	109.5	H25A—C25—H25B	107.8
C8—C7—B1	130.43 (11)	C25—C26—H26A	109.5
C8—C7—S1	109.62 (9)	C25—C26—H26B	109.5
B1—C7—S1	119.94 (9)	H26A—C26—H26B	109.5
C7—C8—C9	114.77 (11)	C25—C26—H26C	109.5
C7—C8—H8	122.6	H26A—C26—H26C	109.5
C9—C8—H8	122.6	H26B—C26—H26C	109.5
C10—C9—C8	111.10 (10)	O3—C27—C29	109.17 (12)
C10—C9—C11	123.51 (11)	O3—C27—C30	105.59 (11)
C8—C9—C11	125.30 (11)	C29—C27—C30	110.59 (14)
C9—C10—C17	128.56 (10)	O3—C27—C28	103.03 (10)
C9—C10—S1	111.59 (9)	C29—C27—C28	115.76 (12)
C17—C10—S1	119.84 (8)	C30—C27—C28	111.90 (12)
C9—C11—C12	111.84 (10)	O4—C28—C31	108.74 (11)
C9—C11—H11A	109.2	O4—C28—C32	106.37 (11)
C12—C11—H11A	109.2	C31—C28—C32	110.03 (12)
C9—C11—H11B	109.2	O4—C28—C27	102.50 (9)
C12—C11—H11B	109.2	C31—C28—C27	115.23 (12)
H11A—C11—H11B	107.9	C32—C28—C27	113.25 (12)
C13—C12—C11	113.99 (11)	C27—C29—H29A	109.5
C13—C12—H12A	108.8	C27—C29—H29B	109.5
C11—C12—H12A	108.8	H29A—C29—H29B	109.5
C13—C12—H12B	108.8	C27—C29—H29C	109.5
C11—C12—H12B	108.8	H29A—C29—H29C	109.5
H12A—C12—H12B	107.6	H29B—C29—H29C	109.5
C12—C13—C14	113.64 (12)	C27—C30—H30A	109.5
C12—C13—H13A	108.8	C27—C30—H30B	109.5
C14—C13—H13A	108.8	H30A—C30—H30B	109.5
C12—C13—H13B	108.8	C27—C30—H30C	109.5
C14—C13—H13B	108.8	H30A—C30—H30C	109.5
H13A—C13—H13B	107.7	H30B—C30—H30C	109.5
C15—C14—C13	113.96 (13)	C28—C31—H31A	109.5
C15—C14—H14A	108.8	C28—C31—H31B	109.5
C13—C14—H14A	108.8	H31A—C31—H31B	109.5
C15—C14—H14B	108.8	C28—C31—H31C	109.5
C13—C14—H14B	108.8	H31A—C31—H31C	109.5
H14A—C14—H14B	107.7	H31B—C31—H31C	109.5
C16—C15—C14	113.33 (14)	C28—C32—H32A	109.5
C16—C15—H15A	108.9	C28—C32—H32B	109.5
C14—C15—H15A	108.9	H32A—C32—H32B	109.5
C16—C15—H15B	108.9	C28—C32—H32C	109.5
C14—C15—H15B	108.9	H32A—C32—H32C	109.5
H15A—C15—H15B	107.7	H32B—C32—H32C	109.5
C15—C16—H16A	109.5	B1—O1—C2	106.83 (9)
C15—C16—H16B	109.5	B1—O2—C5	106.36 (9)
H16A—C16—H16B	109.5	B2—O3—C27	106.50 (10)
C15—C16—H16C	109.5	B2—O4—C28	107.21 (10)
H16A—C16—H16C	109.5	C10—S1—C7	92.91 (6)
H16B—C16—H16C	109.5	C20—S2—C17	92.72 (6)

O1—C2—C5—O2	−28.30 (11)	C17—C18—C21—C22	−121.33 (14)
C1—C2—C5—O2	−145.90 (11)	C19—C18—C21—C22	56.35 (16)
C3—C2—C5—O2	85.67 (12)	C18—C21—C22—C23	−167.13 (12)
O1—C2—C5—C6	−145.95 (11)	C21—C22—C23—C24	−66.75 (18)
C1—C2—C5—C6	96.45 (14)	C22—C23—C24—C25	−177.15 (12)
C3—C2—C5—C6	−31.98 (15)	C23—C24—C25—C26	−71.53 (17)
O1—C2—C5—C4	86.04 (12)	O3—C27—C28—O4	25.36 (13)
C1—C2—C5—C4	−31.56 (15)	C29—C27—C28—O4	144.44 (12)
C3—C2—C5—C4	−159.99 (11)	C30—C27—C28—O4	−87.62 (13)
O2—B1—C7—C8	3.4 (2)	O3—C27—C28—C31	143.28 (12)
O1—B1—C7—C8	−176.39 (12)	C29—C27—C28—C31	−97.64 (16)
O2—B1—C7—S1	−177.69 (10)	C30—C27—C28—C31	30.30 (17)
O1—B1—C7—S1	2.55 (17)	O3—C27—C28—C32	−88.81 (13)
B1—C7—C8—C9	178.53 (12)	C29—C27—C28—C32	30.27 (17)
S1—C7—C8—C9	−0.50 (14)	C30—C27—C28—C32	158.21 (12)
C7—C8—C9—C10	0.85 (15)	O2—B1—O1—C2	−9.18 (14)
C7—C8—C9—C11	−175.73 (11)	C7—B1—O1—C2	170.61 (11)
C8—C9—C10—C17	177.90 (11)	C1—C2—O1—B1	145.43 (12)
C11—C9—C10—C17	−5.45 (19)	C3—C2—O1—B1	−95.90 (12)
C8—C9—C10—S1	−0.80 (13)	C5—C2—O1—B1	23.08 (12)
C11—C9—C10—S1	175.85 (9)	O1—B1—O2—C5	−10.37 (14)
C10—C9—C11—C12	−77.10 (15)	C7—B1—O2—C5	169.85 (11)
C8—C9—C11—C12	99.07 (14)	C6—C5—O2—B1	145.86 (11)
C9—C11—C12—C13	−72.44 (14)	C4—C5—O2—B1	−95.37 (12)
C11—C12—C13—C14	169.15 (11)	C2—C5—O2—B1	23.82 (12)
C12—C13—C14—C15	165.11 (12)	O4—B2—O3—C27	9.09 (15)
C13—C14—C15—C16	176.88 (13)	C20—B2—O3—C27	−172.44 (12)
C9—C10—C17—C18	−68.23 (18)	C29—C27—O3—B2	−144.77 (13)
S1—C10—C17—C18	110.38 (13)	C30—C27—O3—B2	96.31 (13)
C9—C10—C17—S2	114.69 (12)	C28—C27—O3—B2	−21.22 (13)
S1—C10—C17—S2	−66.71 (12)	O3—B2—O4—C28	8.41 (15)
C10—C17—C18—C19	−177.50 (11)	C20—B2—O4—C28	−170.13 (11)
S2—C17—C18—C19	−0.21 (13)	C31—C28—O4—B2	−143.23 (12)
C10—C17—C18—C21	0.4 (2)	C32—C28—O4—B2	98.31 (13)
S2—C17—C18—C21	177.72 (10)	C27—C28—O4—B2	−20.80 (13)
C17—C18—C19—C20	0.33 (15)	C9—C10—S1—C7	0.46 (9)
C21—C18—C19—C20	−177.65 (11)	C17—C10—S1—C7	−178.37 (10)
C18—C19—C20—B2	179.11 (11)	C8—C7—S1—C10	0.02 (10)
C18—C19—C20—S2	−0.30 (14)	B1—C7—S1—C10	−179.12 (10)
O4—B2—C20—C19	15.00 (19)	C19—C20—S2—C17	0.15 (10)
O3—B2—C20—C19	−163.37 (13)	B2—C20—S2—C17	−179.27 (11)
O4—B2—C20—S2	−165.68 (10)	C18—C17—S2—C20	0.04 (9)
O3—B2—C20—S2	15.95 (18)	C10—C17—S2—C20	177.57 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30C···O1ⁱ	0.98	2.53	3.2984 (18)	136

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₂H₅₂B₂O₄S₂
M_r	586.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.5004 (11), 13.6992 (13), 21.300 (2)
β (°)	91.065 (2)
V (Å³)	3355.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	29998, 9743, 8009
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.118, 1.05
No. of reflections	9743
No. of parameters	371
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30C···O1ⁱ	0.98	2.53	3.2984 (18)	135.6

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors are grateful to Xiangfan University for financial support.

References

Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buszek, K. R. & Brown, N. (2007). Org. Lett. 9, 707–710. Web of Science CrossRef PubMed CAS Google Scholar
Decken, A., Zamora, M. T., Duguay, D. R., Vogels, C. M. & Westcott, S. A. (2008). Acta Cryst. E64, o929. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kleeberg, C., Dang, L., Lin, Z. & Marder, T. B. (2009). Angew. Chem. Int. Ed. 48, 5350–5354. Web of Science CSD CrossRef CAS Google Scholar
Montes, V. A., Perez-Bolivar, C., Estrada, L. A., Shinar, J. & Anzenbacher, P. (2007). J. Am. Chem. Soc. 129, 12598–12599. Web of Science CrossRef PubMed CAS Google Scholar
Navarro, O., Kaur, H., Mahjoor, P. & Nolan, S. P. (2004). J. Org. Chem. 69, 3173–3180. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Usta, H., Lu, G., Facchetti, A. & Marks, T. J. (2006). J. Am. Chem. Soc. 128, 9034–9035. Web of Science CrossRef PubMed CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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