organic compounds
4,4,5,5-Tetramethyl-2-[(Z)-1-(3-methylphenoxy)hex-1-en-2-yl]-1,3,2-dioxaborolane
aCollege of Physical Education and Health Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and bCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
*Correspondence e-mail: wangxj@zjnu.cn
The title compound, C19H29BO3, was prepared by the reaction of 1-(hex-1-yn-1-yloxy)-3-methylbenzene in tetrahydrofuran with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane under a nitrogen atmosphere. In the molecule, the butyl group adopts an extended conformation, with a torsion angle of 179.52 (19)°. The dioxaborolane ring has a twisted conformation on the C—C bond, and its mean plane is inclined to the 3-methylphenyl ring by 44.79 (19)°. In the crystal, there are no significant intermolecular interactions present.
Keywords: crystal structure; dioxaborolane; extended conformation.
CCDC reference: 1473545
Structure description
The title compound was previously prepared by Cui et al. (2013), and its derivatives were synthesized by Yang & Cheng (2001) and Whelligan et al. (2010). We present here the of the compound (Fig. 1). In the molecule, the conformation of the dioxaborolane ring is similar to half chair, and the butyl group adopts an extended conformation with a C10—C11—C12—C13 torsion angle = 179.52 (19)°. No hydrogen bonding is observed in the crystal.
Synthesis and crystallization
To a solution of 1-(hex-1-yn-1-yloxy)-3-methylbenzene (94 mg, 0.5 mmol) in 2.0 ml of tetrahydrofuran (THF) was added neat 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) (71 mg, 0.55 mmol) under nitrogen atmosphere. After stirring at room temperature for 1.5 h, the reaction mixture was concentrated and purified by on silica gel (petroleum ether/EtOAc = 60/1).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1473545
10.1107/S2414314616006118/xu4004sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616006118/xu4004Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616006118/xu4004Isup3.mol
checkcif. DOI: 10.1107/S2414314616006118/xu4004sup4.pdf
Supporting information file. DOI: 10.1107/S2414314616006118/xu4004Isup5.cml
To a solution of 1-(hex-1-yn-1-yloxy)-3-methylbenzene (94 mg, 0.5 mmol) in 2.0 ml of tetrahydrofuran (THF) was added neat 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) (71 mg, 0.55 mmol) under nitrogen atmosphere. After stirring at room temperature for 1.5 h, the reaction mixture was concentrated and purified by on silica gel (petroleum ether/EtOAc = 60/1).
The title compound was previously prepared by Cui et al. (2013), and its derivatives were synthesized by Yang & Cheng (2001) and Whelligan et al. (2010). We present here the
of the compound (Fig. 1). In the molecule, the conformation of the dioxaborolane ring is similar to half chair, and the butyl group adopts an extended conformation with a C10—C11—C12—C13 torsion angle = 179.52 (19)°. No hydrogen bonding is observed in the crystal.Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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).Fig. 1. Perspective view of the structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C19H29BO3 | F(000) = 688 |
Mr = 316.23 | Dx = 1.079 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0293 (9) Å | Cell parameters from 4375 reflections |
b = 18.1230 (17) Å | θ = 2.1–27.4° |
c = 10.7973 (10) Å | µ = 0.07 mm−1 |
β = 97.475 (6)° | T = 296 K |
V = 1945.9 (3) Å3 | Block, colourless |
Z = 4 | 0.3 × 0.2 × 0.1 mm |
Bruker APEXII diffractometer | 4375 independent reflections |
Radiation source: fine-focus sealed tube | 2665 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω scans | θmax = 27.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→12 |
Tmin = 0.983, Tmax = 0.993 | k = −23→21 |
30133 measured reflections | l = −13→13 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0826P)2 + 0.1148P] where P = (Fo2 + 2Fc2)/3 |
4375 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C19H29BO3 | V = 1945.9 (3) Å3 |
Mr = 316.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0293 (9) Å | µ = 0.07 mm−1 |
b = 18.1230 (17) Å | T = 296 K |
c = 10.7973 (10) Å | 0.3 × 0.2 × 0.1 mm |
β = 97.475 (6)° |
Bruker APEXII diffractometer | 4375 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2665 reflections with I > 2σ(I) |
Tmin = 0.983, Tmax = 0.993 | Rint = 0.044 |
30133 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.18 e Å−3 |
4375 reflections | Δρmin = −0.18 e Å−3 |
208 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
B1 | 0.66602 (17) | 0.11935 (10) | 0.19395 (16) | 0.0479 (4) | |
O1 | 0.49825 (11) | 0.27876 (7) | 0.01441 (12) | 0.0662 (4) | |
O2 | 0.56737 (11) | 0.06699 (6) | 0.18524 (11) | 0.0620 (4) | |
O3 | 0.78374 (10) | 0.09596 (6) | 0.25964 (11) | 0.0573 (3) | |
C1 | 0.36387 (17) | 0.29473 (9) | −0.02574 (16) | 0.0558 (4) | |
C2 | 0.33922 (18) | 0.33782 (9) | −0.13101 (16) | 0.0587 (4) | |
H2A | 0.4104 | 0.3531 | −0.1721 | 0.070* | |
C3 | 0.2087 (2) | 0.35875 (10) | −0.17633 (18) | 0.0664 (5) | |
C4 | 0.1053 (2) | 0.33435 (12) | −0.1136 (2) | 0.0820 (7) | |
H4A | 0.0170 | 0.3466 | −0.1438 | 0.098* | |
C5 | 0.1308 (2) | 0.29256 (12) | −0.0081 (3) | 0.0882 (7) | |
H5A | 0.0597 | 0.2772 | 0.0331 | 0.106* | |
C6 | 0.26130 (19) | 0.27263 (11) | 0.0386 (2) | 0.0732 (5) | |
H6A | 0.2789 | 0.2450 | 0.1115 | 0.088* | |
C7 | 0.1814 (3) | 0.40687 (14) | −0.2895 (2) | 0.1007 (8) | |
H7C | 0.0864 | 0.4152 | −0.3082 | 0.121* | |
H7B | 0.2137 | 0.3830 | −0.3592 | 0.121* | |
H7A | 0.2266 | 0.4533 | −0.2738 | 0.121* | |
C8 | 0.52791 (17) | 0.21201 (9) | 0.07200 (15) | 0.0548 (4) | |
H8A | 0.4622 | 0.1755 | 0.0649 | 0.066* | |
C9 | 0.64616 (15) | 0.19761 (9) | 0.13719 (14) | 0.0493 (4) | |
C10 | 0.75572 (16) | 0.25522 (10) | 0.15952 (15) | 0.0563 (4) | |
H10B | 0.8418 | 0.2317 | 0.1547 | 0.068* | |
H10A | 0.7419 | 0.2917 | 0.0933 | 0.068* | |
C11 | 0.76153 (18) | 0.29400 (10) | 0.28296 (16) | 0.0632 (5) | |
H11B | 0.7786 | 0.2579 | 0.3494 | 0.076* | |
H11A | 0.6747 | 0.3163 | 0.2891 | 0.076* | |
C12 | 0.8690 (2) | 0.35332 (11) | 0.30207 (18) | 0.0763 (6) | |
H12B | 0.9557 | 0.3308 | 0.2964 | 0.092* | |
H12A | 0.8523 | 0.3890 | 0.2349 | 0.092* | |
C13 | 0.8758 (3) | 0.39323 (13) | 0.4244 (2) | 0.1006 (8) | |
H13C | 0.9454 | 0.4299 | 0.4295 | 0.121* | |
H13B | 0.8954 | 0.3587 | 0.4917 | 0.121* | |
H13A | 0.7911 | 0.4167 | 0.4304 | 0.121* | |
C14 | 0.62832 (19) | −0.00170 (9) | 0.23442 (18) | 0.0635 (5) | |
C15 | 0.75651 (16) | 0.02563 (10) | 0.31787 (16) | 0.0565 (4) | |
C16 | 0.6612 (3) | −0.04561 (13) | 0.1223 (2) | 0.1110 (9) | |
H16C | 0.5792 | −0.0618 | 0.0741 | 0.133* | |
H16B | 0.7147 | −0.0877 | 0.1505 | 0.133* | |
H16A | 0.7103 | −0.0150 | 0.0715 | 0.133* | |
C17 | 0.5277 (2) | −0.04152 (15) | 0.3024 (3) | 0.1157 (10) | |
H17C | 0.4526 | −0.0567 | 0.2436 | 0.139* | |
H17B | 0.4971 | −0.0091 | 0.3630 | 0.139* | |
H17A | 0.5694 | −0.0841 | 0.3438 | 0.139* | |
C18 | 0.8788 (2) | −0.02308 (12) | 0.3206 (2) | 0.0831 (6) | |
H18C | 0.8927 | −0.0352 | 0.2367 | 0.100* | |
H18B | 0.8653 | −0.0675 | 0.3656 | 0.100* | |
H18A | 0.9562 | 0.0025 | 0.3612 | 0.100* | |
C19 | 0.7334 (3) | 0.04403 (14) | 0.45048 (18) | 0.0917 (7) | |
H19C | 0.6552 | 0.0747 | 0.4487 | 0.110* | |
H19B | 0.8103 | 0.0697 | 0.4918 | 0.110* | |
H19A | 0.7201 | −0.0007 | 0.4948 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
B1 | 0.0444 (10) | 0.0490 (10) | 0.0490 (9) | −0.0016 (8) | 0.0007 (8) | −0.0027 (8) |
O1 | 0.0523 (7) | 0.0530 (7) | 0.0881 (9) | −0.0010 (5) | −0.0104 (6) | 0.0185 (6) |
O2 | 0.0509 (7) | 0.0507 (7) | 0.0791 (8) | −0.0044 (5) | −0.0114 (6) | 0.0111 (6) |
O3 | 0.0468 (6) | 0.0527 (7) | 0.0689 (7) | −0.0018 (5) | −0.0065 (5) | 0.0086 (6) |
C1 | 0.0504 (10) | 0.0473 (9) | 0.0661 (10) | 0.0005 (7) | −0.0056 (8) | −0.0005 (8) |
C2 | 0.0585 (11) | 0.0536 (10) | 0.0615 (10) | 0.0058 (8) | −0.0012 (8) | 0.0016 (8) |
C3 | 0.0666 (12) | 0.0567 (11) | 0.0705 (11) | 0.0123 (9) | −0.0117 (9) | −0.0080 (9) |
C4 | 0.0536 (12) | 0.0669 (13) | 0.1195 (18) | 0.0088 (10) | −0.0116 (12) | −0.0070 (13) |
C5 | 0.0605 (13) | 0.0714 (14) | 0.136 (2) | 0.0021 (11) | 0.0232 (12) | 0.0120 (14) |
C6 | 0.0678 (12) | 0.0633 (12) | 0.0886 (14) | 0.0002 (10) | 0.0104 (10) | 0.0164 (10) |
C7 | 0.1099 (18) | 0.0981 (18) | 0.0862 (15) | 0.0364 (15) | −0.0170 (13) | 0.0121 (13) |
C8 | 0.0571 (10) | 0.0424 (9) | 0.0620 (10) | −0.0049 (7) | −0.0037 (8) | 0.0053 (7) |
C9 | 0.0471 (9) | 0.0484 (9) | 0.0506 (9) | −0.0010 (7) | −0.0004 (7) | 0.0011 (7) |
C10 | 0.0530 (10) | 0.0553 (10) | 0.0593 (10) | −0.0056 (8) | 0.0020 (7) | 0.0041 (8) |
C11 | 0.0690 (12) | 0.0538 (10) | 0.0662 (11) | −0.0074 (8) | 0.0065 (9) | −0.0014 (8) |
C12 | 0.0868 (14) | 0.0681 (13) | 0.0716 (12) | −0.0258 (11) | 0.0013 (10) | −0.0003 (10) |
C13 | 0.136 (2) | 0.0864 (16) | 0.0765 (14) | −0.0390 (15) | 0.0029 (14) | −0.0076 (12) |
C14 | 0.0657 (11) | 0.0445 (9) | 0.0749 (12) | −0.0028 (8) | −0.0108 (9) | 0.0092 (8) |
C15 | 0.0546 (10) | 0.0541 (10) | 0.0586 (9) | 0.0042 (8) | −0.0011 (7) | 0.0093 (8) |
C16 | 0.160 (2) | 0.0626 (14) | 0.0960 (17) | 0.0129 (15) | −0.0365 (16) | −0.0184 (12) |
C17 | 0.0818 (16) | 0.0952 (18) | 0.164 (3) | −0.0247 (14) | −0.0082 (16) | 0.0607 (18) |
C18 | 0.0690 (13) | 0.0736 (14) | 0.1030 (16) | 0.0160 (11) | −0.0028 (11) | 0.0132 (12) |
C19 | 0.1162 (18) | 0.0980 (17) | 0.0586 (12) | 0.0114 (14) | 0.0023 (11) | 0.0079 (11) |
B1—O3 | 1.363 (2) | C11—C12 | 1.517 (2) |
B1—O2 | 1.365 (2) | C11—H11B | 0.9700 |
B1—C9 | 1.548 (2) | C11—H11A | 0.9700 |
O1—C8 | 1.3749 (19) | C12—C13 | 1.500 (3) |
O1—C1 | 1.3914 (19) | C12—H12B | 0.9700 |
O2—C14 | 1.456 (2) | C12—H12A | 0.9700 |
O3—C15 | 1.463 (2) | C13—H13C | 0.9600 |
C1—C6 | 1.374 (3) | C13—H13B | 0.9600 |
C1—C2 | 1.375 (2) | C13—H13A | 0.9600 |
C2—C3 | 1.390 (2) | C14—C17 | 1.506 (3) |
C2—H2A | 0.9300 | C14—C16 | 1.520 (3) |
C3—C4 | 1.383 (3) | C14—C15 | 1.552 (2) |
C3—C7 | 1.498 (3) | C15—C18 | 1.508 (2) |
C4—C5 | 1.364 (3) | C15—C19 | 1.517 (3) |
C4—H4A | 0.9300 | C16—H16C | 0.9600 |
C5—C6 | 1.388 (3) | C16—H16B | 0.9600 |
C5—H5A | 0.9300 | C16—H16A | 0.9600 |
C6—H6A | 0.9300 | C17—H17C | 0.9600 |
C7—H7C | 0.9600 | C17—H17B | 0.9600 |
C7—H7B | 0.9600 | C17—H17A | 0.9600 |
C7—H7A | 0.9600 | C18—H18C | 0.9600 |
C8—C9 | 1.324 (2) | C18—H18B | 0.9600 |
C8—H8A | 0.9300 | C18—H18A | 0.9600 |
C9—C10 | 1.512 (2) | C19—H19C | 0.9600 |
C10—C11 | 1.501 (2) | C19—H19B | 0.9600 |
C10—H10B | 0.9700 | C19—H19A | 0.9600 |
C10—H10A | 0.9700 | ||
O3—B1—O2 | 112.99 (15) | C13—C12—C11 | 114.32 (18) |
O3—B1—C9 | 123.30 (15) | C13—C12—H12B | 108.7 |
O2—B1—C9 | 123.70 (14) | C11—C12—H12B | 108.7 |
C8—O1—C1 | 117.89 (13) | C13—C12—H12A | 108.7 |
B1—O2—C14 | 107.64 (12) | C11—C12—H12A | 108.7 |
B1—O3—C15 | 107.28 (12) | H12B—C12—H12A | 107.6 |
C6—C1—C2 | 121.19 (17) | C12—C13—H13C | 109.5 |
C6—C1—O1 | 122.72 (16) | C12—C13—H13B | 109.5 |
C2—C1—O1 | 116.00 (15) | H13C—C13—H13B | 109.5 |
C1—C2—C3 | 120.40 (18) | C12—C13—H13A | 109.5 |
C1—C2—H2A | 119.8 | H13C—C13—H13A | 109.5 |
C3—C2—H2A | 119.8 | H13B—C13—H13A | 109.5 |
C4—C3—C2 | 118.19 (18) | O2—C14—C17 | 108.13 (16) |
C4—C3—C7 | 121.14 (19) | O2—C14—C16 | 106.33 (15) |
C2—C3—C7 | 120.7 (2) | C17—C14—C16 | 111.4 (2) |
C5—C4—C3 | 121.04 (19) | O2—C14—C15 | 102.45 (13) |
C5—C4—H4A | 119.5 | C17—C14—C15 | 115.27 (17) |
C3—C4—H4A | 119.5 | C16—C14—C15 | 112.36 (18) |
C4—C5—C6 | 120.9 (2) | O3—C15—C18 | 108.75 (14) |
C4—C5—H5A | 119.6 | O3—C15—C19 | 105.91 (15) |
C6—C5—H5A | 119.6 | C18—C15—C19 | 109.50 (16) |
C1—C6—C5 | 118.26 (19) | O3—C15—C14 | 102.45 (12) |
C1—C6—H6A | 120.9 | C18—C15—C14 | 115.77 (16) |
C5—C6—H6A | 120.9 | C19—C15—C14 | 113.67 (16) |
C3—C7—H7C | 109.5 | C14—C16—H16C | 109.5 |
C3—C7—H7B | 109.5 | C14—C16—H16B | 109.5 |
H7C—C7—H7B | 109.5 | H16C—C16—H16B | 109.5 |
C3—C7—H7A | 109.5 | C14—C16—H16A | 109.5 |
H7C—C7—H7A | 109.5 | H16C—C16—H16A | 109.5 |
H7B—C7—H7A | 109.5 | H16B—C16—H16A | 109.5 |
C9—C8—O1 | 122.69 (15) | C14—C17—H17C | 109.5 |
C9—C8—H8A | 118.7 | C14—C17—H17B | 109.5 |
O1—C8—H8A | 118.7 | H17C—C17—H17B | 109.5 |
C8—C9—C10 | 122.06 (15) | C14—C17—H17A | 109.5 |
C8—C9—B1 | 116.84 (14) | H17C—C17—H17A | 109.5 |
C10—C9—B1 | 121.07 (13) | H17B—C17—H17A | 109.5 |
C11—C10—C9 | 114.10 (14) | C15—C18—H18C | 109.5 |
C11—C10—H10B | 108.7 | C15—C18—H18B | 109.5 |
C9—C10—H10B | 108.7 | H18C—C18—H18B | 109.5 |
C11—C10—H10A | 108.7 | C15—C18—H18A | 109.5 |
C9—C10—H10A | 108.7 | H18C—C18—H18A | 109.5 |
H10B—C10—H10A | 107.6 | H18B—C18—H18A | 109.5 |
C10—C11—C12 | 113.41 (15) | C15—C19—H19C | 109.5 |
C10—C11—H11B | 108.9 | C15—C19—H19B | 109.5 |
C12—C11—H11B | 108.9 | H19C—C19—H19B | 109.5 |
C10—C11—H11A | 108.9 | C15—C19—H19A | 109.5 |
C12—C11—H11A | 108.9 | H19C—C19—H19A | 109.5 |
H11B—C11—H11A | 107.7 | H19B—C19—H19A | 109.5 |
O3—B1—O2—C14 | −8.47 (19) | O3—B1—C9—C10 | −4.3 (2) |
C9—B1—O2—C14 | 172.46 (15) | O2—B1—C9—C10 | 174.71 (15) |
O2—B1—O3—C15 | −9.78 (18) | C8—C9—C10—C11 | 96.8 (2) |
C9—B1—O3—C15 | 169.30 (15) | B1—C9—C10—C11 | −81.07 (19) |
C8—O1—C1—C6 | 35.4 (2) | C9—C10—C11—C12 | −178.12 (16) |
C8—O1—C1—C2 | −148.01 (16) | C10—C11—C12—C13 | 179.52 (19) |
C6—C1—C2—C3 | −1.4 (3) | B1—O2—C14—C17 | 143.74 (18) |
O1—C1—C2—C3 | −178.00 (15) | B1—O2—C14—C16 | −96.49 (19) |
C1—C2—C3—C4 | −0.7 (3) | B1—O2—C14—C15 | 21.59 (17) |
C1—C2—C3—C7 | 178.83 (18) | B1—O3—C15—C18 | 145.33 (15) |
C2—C3—C4—C5 | 1.8 (3) | B1—O3—C15—C19 | −97.07 (16) |
C7—C3—C4—C5 | −177.8 (2) | B1—O3—C15—C14 | 22.30 (17) |
C3—C4—C5—C6 | −0.7 (3) | O2—C14—C15—O3 | −26.26 (17) |
C2—C1—C6—C5 | 2.4 (3) | C17—C14—C15—O3 | −143.43 (17) |
O1—C1—C6—C5 | 178.81 (18) | C16—C14—C15—O3 | 87.46 (18) |
C4—C5—C6—C1 | −1.4 (3) | O2—C14—C15—C18 | −144.43 (16) |
C1—O1—C8—C9 | −164.95 (16) | C17—C14—C15—C18 | 98.4 (2) |
O1—C8—C9—C10 | 3.5 (3) | C16—C14—C15—C18 | −30.7 (2) |
O1—C8—C9—B1 | −178.53 (15) | O2—C14—C15—C19 | 87.53 (18) |
O3—B1—C9—C8 | 177.75 (15) | C17—C14—C15—C19 | −29.6 (2) |
O2—B1—C9—C8 | −3.3 (2) | C16—C14—C15—C19 | −158.76 (18) |
Experimental details
Crystal data | |
Chemical formula | C19H29BO3 |
Mr | 316.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 10.0293 (9), 18.1230 (17), 10.7973 (10) |
β (°) | 97.475 (6) |
V (Å3) | 1945.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.3 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Bruker APEXII |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.983, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30133, 4375, 2665 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.168, 1.09 |
No. of reflections | 4375 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The work was supported by the chemical weight of the open fund (No. ZC323015033).
References
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cui, W.-J., Mao, M.-Y., He, Z.-Y. & Zhu, G.-G. (2013). J. Org. Chem. 78, 9815–9821. CrossRef CAS PubMed 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
Whelligan, D. K., Thomson, D. W., Taylor, D. & Hoelder, S. (2010). J. Org. Chem. 75, 11–15. CrossRef PubMed CAS Google Scholar
Yang, F.-Y. & Cheng, C.-H. (2001). J. Am. Chem. Soc. 123, 761–762. CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound was previously prepared by Cui et al. (2013), and its derivatives were synthesized by Yang & Cheng (2001) and Whelligan et al. (2010). We present here the crystal structure of the compound. In teh molecule, the conformation of the dioxaborolane ring is similar to half chair, and the butyl group adopts an extended conformation with the C10–C11–C12–C13 torsion angle = 179.52 (19)°. No hydrogen bonding is observed in the crystal.