(E)-2-(1,1-Di-cyclo-hexyl-3-phenyl-all-yl)-5,5-dimethyl-1,3,2-dioxaborinane.

The crystal structure of the title compound, C26H39BO2, which contains no strong hydrogen bond donors, displays only long C-H⋯O contacts between inversion-related pairs of mol-ecules. The structure contains layers rich in oxygen and boron parallel to the ac plane. The dioxaborinane ring adopts an envelope conformation with the C atom attached to the two methyl groups as the flap .

Related literature

For the synthesis and applications of allyl­boronic esters, see: Lombardo et al. (2002 ▶); Carosi & Hall (2007 ▶); Althaus et al. (2010 ▶); Fandrick et al. (2010 ▶); Clary et al. (2011 ▶); Hesse et al. (2012 ▶); Incerti-Pradillos et al. (2013 ▶). For the X-ray structure of a boronic ester, see: Sopková-de Oliveira Santos et al. (2003 ▶).

Experimental

Crystal data

C26H39BO2

M = 394.38

Triclinic,

a = 9.4967 (3) Å

b = 11.2837 (2) Å

c = 12.0297 (4) Å

α = 109.897 (2)°

β = 96.388 (2)°

γ = 102.048 (2)°

V = 1161.90 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 150 K

0.38 × 0.30 × 0.28 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.975, T max = 0.981

8277 measured reflections

5287 independent reflections

4303 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.128

S = 1.03

5287 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP99 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CHEMDRAW Ultra (Cambridge Soft, 2001 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813021739/go2094sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021739/go2094Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021739/go2094Isup3.cml

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

C26H39BO2	Z = 2
Mr = 394.38	F(000) = 432
Triclinic, P1	Dx = 1.127 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4967 (3) Å	Cell parameters from 4303 reflections
b = 11.2837 (2) Å	θ = 2.2–27.5°
c = 12.0297 (4) Å	µ = 0.07 mm−1
α = 109.897 (2)°	T = 150 K
β = 96.388 (2)°	Block, colourless
γ = 102.048 (2)°	0.38 × 0.30 × 0.28 mm
V = 1161.90 (6) Å3

Nonius KappaCCD diffractometer	5287 independent reflections
Radiation source: fine-focus sealed tube	4303 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
CCD slices, ω and phi scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −12→12
Tmin = 0.975, Tmax = 0.981	k = −14→14
8277 measured reflections	l = −15→12

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.4651P] where P = (Fo2 + 2Fc2)/3
5287 reflections	(Δ/σ)max = 0.004
264 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
C1	0.24096 (15)	0.23892 (13)	0.62817 (11)	0.0235 (3)
C2	0.22913 (18)	0.35166 (15)	0.71836 (13)	0.0348 (3)
H2	0.2828	0.4349	0.7232	0.042*
C3	0.14007 (19)	0.34351 (17)	0.80085 (14)	0.0411 (4)
H3	0.1319	0.4211	0.8607	0.049*
C4	0.06330 (17)	0.22337 (17)	0.79648 (14)	0.0382 (4)
H4	0.0029	0.2179	0.8534	0.046*
C5	0.07497 (17)	0.11101 (16)	0.70869 (14)	0.0348 (3)
H5	0.0228	0.0280	0.7055	0.042*
C6	0.16250 (16)	0.11876 (13)	0.62506 (13)	0.0281 (3)
H6	0.1689	0.0407	0.5648	0.034*
C7	0.33581 (15)	0.25145 (13)	0.54118 (12)	0.0255 (3)
H7	0.4098	0.3312	0.5644	0.031*
C8	0.32693 (14)	0.16134 (12)	0.43362 (11)	0.0221 (3)
H8	0.2530	0.0818	0.4117	0.027*
C9	0.42193 (14)	0.17080 (12)	0.34118 (11)	0.0205 (3)
C10	0.58492 (14)	0.24810 (12)	0.40612 (11)	0.0218 (3)
H10	0.5813	0.3293	0.4725	0.026*
C11	0.65750 (15)	0.16852 (13)	0.46484 (12)	0.0260 (3)
H11A	0.5978	0.1466	0.5210	0.031*
H11B	0.6589	0.0856	0.4014	0.031*
C12	0.81407 (16)	0.24166 (14)	0.53369 (13)	0.0330 (3)
H12A	0.8121	0.3195	0.6031	0.040*
H12B	0.8576	0.1844	0.5655	0.040*
C13	0.90896 (17)	0.28434 (15)	0.45299 (15)	0.0380 (4)
H13A	0.9200	0.2064	0.3883	0.046*
H13B	1.0079	0.3364	0.5010	0.046*
C14	0.83863 (17)	0.36592 (15)	0.39717 (15)	0.0361 (4)
H14A	0.8996	0.3908	0.3430	0.043*
H14B	0.8349	0.4471	0.4618	0.043*
C15	0.68323 (15)	0.29066 (13)	0.32573 (13)	0.0283 (3)
H15A	0.6875	0.2125	0.2577	0.034*
H15B	0.6400	0.3466	0.2918	0.034*
C16	0.35441 (15)	0.23557 (12)	0.25946 (12)	0.0229 (3)
H16	0.4152	0.2331	0.1963	0.027*
C17	0.19670 (16)	0.16006 (14)	0.19300 (13)	0.0309 (3)
H17A	0.1928	0.0671	0.1500	0.037*
H17B	0.1315	0.1645	0.2522	0.037*
C18	0.14178 (19)	0.21631 (17)	0.10238 (15)	0.0404 (4)
H18A	0.2011	0.2042	0.0387	0.048*
H18B	0.0384	0.1683	0.0635	0.048*
C19	0.1523 (2)	0.36161 (18)	0.16395 (16)	0.0436 (4)
H19A	0.1255	0.3970	0.1021	0.052*
H19B	0.0814	0.3726	0.2187	0.052*
C20	0.30661 (19)	0.43826 (15)	0.23583 (14)	0.0364 (4)
H20A	0.3073	0.5301	0.2804	0.044*
H20B	0.3754	0.4379	0.1797	0.044*
C21	0.35828 (17)	0.37906 (13)	0.32525 (13)	0.0287 (3)
H21A	0.4597	0.4290	0.3689	0.034*
H21B	0.2940	0.3855	0.3852	0.034*
C22	0.51831 (16)	−0.10974 (13)	0.09454 (13)	0.0290 (3)
H22A	0.6131	−0.1146	0.1338	0.035*
H22B	0.5259	−0.1158	0.0115	0.035*
C23	0.39668 (15)	−0.22485 (12)	0.08888 (12)	0.0256 (3)
C24	0.37886 (18)	−0.20513 (13)	0.21769 (12)	0.0301 (3)
H24A	0.2915	−0.2720	0.2158	0.036*
H24B	0.4659	−0.2183	0.2607	0.036*
C25	0.25412 (17)	−0.23168 (15)	0.01216 (14)	0.0363 (4)
H25A	0.1768	−0.3060	0.0092	0.055*
H25B	0.2688	−0.2427	−0.0697	0.055*
H25C	0.2250	−0.1507	0.0477	0.055*
C26	0.44291 (19)	−0.35104 (14)	0.03502 (14)	0.0373 (4)
H26A	0.5375	−0.3438	0.0822	0.056*
H26B	0.4524	−0.3656	−0.0486	0.056*
H26C	0.3685	−0.4246	0.0369	0.056*
B1	0.42494 (16)	0.02685 (14)	0.25703 (13)	0.0210 (3)
O1	0.36243 (11)	−0.07729 (8)	0.28350 (8)	0.0261 (2)
O2	0.49222 (11)	0.01427 (9)	0.16035 (8)	0.0273 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0250 (7)	0.0294 (6)	0.0191 (6)	0.0096 (5)	0.0060 (5)	0.0110 (5)
C2	0.0404 (9)	0.0318 (7)	0.0276 (7)	0.0065 (6)	0.0118 (6)	0.0056 (6)
C3	0.0444 (9)	0.0484 (9)	0.0257 (8)	0.0151 (8)	0.0147 (7)	0.0040 (7)
C4	0.0306 (8)	0.0644 (10)	0.0285 (8)	0.0168 (7)	0.0142 (6)	0.0232 (7)
C5	0.0303 (8)	0.0443 (8)	0.0394 (8)	0.0094 (6)	0.0119 (6)	0.0263 (7)
C6	0.0299 (7)	0.0298 (7)	0.0296 (7)	0.0115 (6)	0.0099 (6)	0.0138 (6)
C7	0.0291 (7)	0.0248 (6)	0.0240 (7)	0.0063 (5)	0.0094 (5)	0.0102 (5)
C8	0.0238 (7)	0.0240 (6)	0.0219 (6)	0.0079 (5)	0.0073 (5)	0.0108 (5)
C9	0.0243 (6)	0.0216 (6)	0.0188 (6)	0.0083 (5)	0.0072 (5)	0.0092 (5)
C10	0.0229 (6)	0.0225 (6)	0.0210 (6)	0.0072 (5)	0.0066 (5)	0.0081 (5)
C11	0.0286 (7)	0.0282 (6)	0.0230 (7)	0.0092 (5)	0.0049 (5)	0.0106 (5)
C12	0.0309 (8)	0.0338 (7)	0.0318 (8)	0.0121 (6)	0.0013 (6)	0.0085 (6)
C13	0.0264 (8)	0.0372 (8)	0.0450 (9)	0.0078 (6)	0.0061 (7)	0.0093 (7)
C14	0.0276 (8)	0.0352 (8)	0.0442 (9)	0.0035 (6)	0.0120 (7)	0.0145 (7)
C15	0.0285 (7)	0.0301 (7)	0.0295 (7)	0.0067 (6)	0.0111 (6)	0.0140 (6)
C16	0.0265 (7)	0.0262 (6)	0.0219 (6)	0.0114 (5)	0.0088 (5)	0.0123 (5)
C17	0.0295 (8)	0.0356 (7)	0.0295 (7)	0.0114 (6)	0.0042 (6)	0.0136 (6)
C18	0.0355 (9)	0.0569 (10)	0.0353 (8)	0.0190 (8)	0.0016 (7)	0.0228 (7)
C19	0.0482 (10)	0.0627 (11)	0.0443 (9)	0.0370 (9)	0.0182 (8)	0.0340 (8)
C20	0.0511 (10)	0.0379 (8)	0.0391 (8)	0.0276 (7)	0.0211 (7)	0.0244 (7)
C21	0.0378 (8)	0.0276 (7)	0.0282 (7)	0.0158 (6)	0.0107 (6)	0.0142 (5)
C22	0.0338 (8)	0.0268 (7)	0.0280 (7)	0.0129 (6)	0.0142 (6)	0.0067 (5)
C23	0.0303 (7)	0.0246 (6)	0.0224 (7)	0.0103 (5)	0.0080 (5)	0.0068 (5)
C24	0.0475 (9)	0.0219 (6)	0.0245 (7)	0.0128 (6)	0.0112 (6)	0.0096 (5)
C25	0.0369 (9)	0.0403 (8)	0.0265 (7)	0.0126 (7)	0.0036 (6)	0.0054 (6)
C26	0.0498 (10)	0.0284 (7)	0.0339 (8)	0.0173 (7)	0.0133 (7)	0.0064 (6)
B1	0.0235 (7)	0.0238 (7)	0.0179 (7)	0.0080 (5)	0.0047 (5)	0.0094 (5)
O1	0.0400 (6)	0.0207 (4)	0.0199 (5)	0.0090 (4)	0.0112 (4)	0.0082 (4)
O2	0.0363 (6)	0.0229 (4)	0.0255 (5)	0.0100 (4)	0.0153 (4)	0.0083 (4)

C1—C6	1.3902 (19)	C16—C17	1.531 (2)
C1—C2	1.3983 (18)	C16—C21	1.5316 (17)
C1—C7	1.4777 (17)	C16—H16	1.0000
C2—C3	1.388 (2)	C17—C18	1.532 (2)
C2—H2	0.9500	C17—H17A	0.9900
C3—C4	1.379 (2)	C17—H17B	0.9900
C3—H3	0.9500	C18—C19	1.528 (2)
C4—C5	1.381 (2)	C18—H18A	0.9900
C4—H4	0.9500	C18—H18B	0.9900
C5—C6	1.3879 (19)	C19—C20	1.524 (3)
C5—H5	0.9500	C19—H19A	0.9900
C6—H6	0.9500	C19—H19B	0.9900
C7—C8	1.3264 (18)	C20—C21	1.5338 (19)
C7—H7	0.9500	C20—H20A	0.9900
C8—C9	1.5251 (16)	C20—H20B	0.9900
C8—H8	0.9500	C21—H21A	0.9900
C9—C16	1.5672 (17)	C21—H21B	0.9900
C9—C10	1.5717 (18)	C22—O2	1.4424 (15)
C9—B1	1.6034 (18)	C22—C23	1.5238 (19)
C10—C11	1.5369 (18)	C22—H22A	0.9900
C10—C15	1.5386 (17)	C22—H22B	0.9900
C10—H10	1.0000	C23—C24	1.5227 (18)
C11—C12	1.525 (2)	C23—C25	1.523 (2)
C11—H11A	0.9900	C23—C26	1.5285 (18)
C11—H11B	0.9900	C24—O1	1.4408 (15)
C12—C13	1.523 (2)	C24—H24A	0.9900
C12—H12A	0.9900	C24—H24B	0.9900
C12—H12B	0.9900	C25—H25A	0.9800
C13—C14	1.524 (2)	C25—H25B	0.9800
C13—H13A	0.9900	C25—H25C	0.9800
C13—H13B	0.9900	C26—H26A	0.9800
C14—C15	1.528 (2)	C26—H26B	0.9800
C14—H14A	0.9900	C26—H26C	0.9800
C14—H14B	0.9900	B1—O1	1.3565 (17)
C15—H15A	0.9900	B1—O2	1.3682 (16)
C15—H15B	0.9900
C6—C1—C2	117.89 (12)	C17—C16—H16	106.8
C6—C1—C7	122.74 (12)	C21—C16—H16	106.8
C2—C1—C7	119.37 (12)	C9—C16—H16	106.8
C3—C2—C1	120.89 (14)	C18—C17—C16	111.14 (12)
C3—C2—H2	119.6	C18—C17—H17A	109.4
C1—C2—H2	119.6	C16—C17—H17A	109.4
C4—C3—C2	120.37 (14)	C18—C17—H17B	109.4
C4—C3—H3	119.8	C16—C17—H17B	109.4
C2—C3—H3	119.8	H17A—C17—H17B	108.0
C3—C4—C5	119.46 (13)	C19—C18—C17	111.29 (13)
C3—C4—H4	120.3	C19—C18—H18A	109.4
C5—C4—H4	120.3	C17—C18—H18A	109.4
C4—C5—C6	120.36 (14)	C19—C18—H18B	109.4
C4—C5—H5	119.8	C17—C18—H18B	109.4
C6—C5—H5	119.8	H18A—C18—H18B	108.0
C5—C6—C1	121.03 (13)	C20—C19—C18	111.51 (12)
C5—C6—H6	119.5	C20—C19—H19A	109.3
C1—C6—H6	119.5	C18—C19—H19A	109.3
C8—C7—C1	125.85 (12)	C20—C19—H19B	109.3
C8—C7—H7	117.1	C18—C19—H19B	109.3
C1—C7—H7	117.1	H19A—C19—H19B	108.0
C7—C8—C9	127.42 (12)	C19—C20—C21	111.18 (13)
C7—C8—H8	116.3	C19—C20—H20A	109.4
C9—C8—H8	116.3	C21—C20—H20A	109.4
C8—C9—C16	109.58 (10)	C19—C20—H20B	109.4
C8—C9—C10	110.43 (10)	C21—C20—H20B	109.4
C16—C9—C10	111.93 (10)	H20A—C20—H20B	108.0
C8—C9—B1	109.36 (10)	C16—C21—C20	110.77 (12)
C16—C9—B1	108.39 (10)	C16—C21—H21A	109.5
C10—C9—B1	107.06 (10)	C20—C21—H21A	109.5
C11—C10—C15	109.13 (11)	C16—C21—H21B	109.5
C11—C10—C9	110.54 (10)	C20—C21—H21B	109.5
C15—C10—C9	115.16 (11)	H21A—C21—H21B	108.1
C11—C10—H10	107.2	O2—C22—C23	112.27 (10)
C15—C10—H10	107.2	O2—C22—H22A	109.2
C9—C10—H10	107.2	C23—C22—H22A	109.2
C12—C11—C10	112.66 (11)	O2—C22—H22B	109.2
C12—C11—H11A	109.1	C23—C22—H22B	109.2
C10—C11—H11A	109.1	H22A—C22—H22B	107.9
C12—C11—H11B	109.1	C24—C23—C25	111.00 (12)
C10—C11—H11B	109.1	C24—C23—C22	107.48 (11)
H11A—C11—H11B	107.8	C25—C23—C22	110.22 (12)
C13—C12—C11	111.29 (12)	C24—C23—C26	108.90 (12)
C13—C12—H12A	109.4	C25—C23—C26	110.06 (12)
C11—C12—H12A	109.4	C22—C23—C26	109.12 (11)
C13—C12—H12B	109.4	O1—C24—C23	112.89 (11)
C11—C12—H12B	109.4	O1—C24—H24A	109.0
H12A—C12—H12B	108.0	C23—C24—H24A	109.0
C12—C13—C14	110.08 (12)	O1—C24—H24B	109.0
C12—C13—H13A	109.6	C23—C24—H24B	109.0
C14—C13—H13A	109.6	H24A—C24—H24B	107.8
C12—C13—H13B	109.6	C23—C25—H25A	109.5
C14—C13—H13B	109.6	C23—C25—H25B	109.5
H13A—C13—H13B	108.2	H25A—C25—H25B	109.5
C13—C14—C15	111.34 (12)	C23—C25—H25C	109.5
C13—C14—H14A	109.4	H25A—C25—H25C	109.5
C15—C14—H14A	109.4	H25B—C25—H25C	109.5
C13—C14—H14B	109.4	C23—C26—H26A	109.5
C15—C14—H14B	109.4	C23—C26—H26B	109.5
H14A—C14—H14B	108.0	H26A—C26—H26B	109.5
C14—C15—C10	111.18 (12)	C23—C26—H26C	109.5
C14—C15—H15A	109.4	H26A—C26—H26C	109.5
C10—C15—H15A	109.4	H26B—C26—H26C	109.5
C14—C15—H15B	109.4	O1—B1—O2	122.35 (11)
C10—C15—H15B	109.4	O1—B1—C9	119.72 (11)
H15A—C15—H15B	108.0	O2—B1—C9	117.93 (11)
C17—C16—C21	108.63 (11)	B1—O1—C24	120.49 (10)
C17—C16—C9	112.83 (11)	B1—O2—C22	119.36 (10)
C21—C16—C9	114.57 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22B···O2i	0.99	2.69	3.5773 (18)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22B⋯O2i	0.99	2.69	3.5773 (18)	150

Symmetry code: (i) .