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In the title compound, C7H14BNO2, the B—N distance is 1.659 (4) Å. Molecules are linked through intermolecular N—H...O hydrogen bonds to form infinite chains with an N...O distance of 2.907 (3) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011679/om6035sup1.cif
Contains datablocks k98221, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011679/om6035Isup2.hkl
Contains datablock I

CCDC reference: 170920

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.063
  • wR factor = 0.176
  • Data-to-parameter ratio = 16.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.138
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The reaction of allylboron reagents and its derivatives with carbonyl compounds is one of the most important reactions in organic synthesis. Many allylboron compounds, however, are sensitive to air and/or moisture and require special handling procedures. In view of this, the development of stable variants of allylboronic acid is an important task. We have recently synthesized potassium allyltrifluoroborate and demonstrated its synthetic utility in aqueous and organic media (Batey et al., 2000; Batey & Thadani, 2001). The title compound, (I), is another stable variant that reacts with aldehydes to afford the corresponding homoallylic alcohols in moderate to good yields in dichloromethane. Both potassium allyltrifluoroborate and (I) are stable to air and/or moisture and can be stored for extended periods without any special precautions.

Molecules of (I) are linked by hydrogen bonds to form infinite chains through glide-plane transformations along the c axes, with a distance for N1···O1 of 2.903 (3) Å (see Fig. 2 and Table 2). A search of the April 2001 release of the Cambridge Structural Database (Allen & Kennard, 1993) revealed the structures of four other dioxazaborocine compounds [with refcodes COQRAB (Doidge-Harrison et al., 1998), PBORXZ (Rettig & Trotter, 1975), PUTBUB (Caron & Hawkins, 1998) and SIBGIT (Howie et al., 1997)]. The B—N distance in these compounds ranges from 1.657 to 1.672 Å and in (I), the B1—N1 distance is 1.659 (4) Å. [Dear Alan, I have added the references for the refcodes as this is required by Acta journals. I would be grateful if you would check that they are correct and provide final page numbers if possible – Sean]

Experimental top

To a solution of allylboronic acid (Brown et al., 1990) (1 equivalent) in a minimal amount of iPrOH was added diethanolamine (1 equivalent). The reaction mixture was stirred for 2 h at room temperature. The solvent was then removed under reduced pressure and the resulting solid recrystallized from acetonitrile. The title compound was obtained in 66% yield as clear colourless needles.

Refinement top

H atoms were included in calculated positions with C—H distances ranging from 0.95 to 0.99 Å and an N—H distance of 0.93 Å.

Computing details top

Data collection: COLLECT (Nonius, 1997-2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of (I) showing the atom-labelling scheme. Ellipsoids are at the 50% probability level. H atoms bonded to C atoms have been removed for the sake of clarity.
[Figure 2] Fig. 2. View of the hydrogen bonding in (I) showing infinite chains in the z direction. Ellipsoids are at the 50% probability level. H atoms bonded to C atoms have been removed for the sake of clarity.
4,5,7,8-Tetrahydro-2-(2-Propenyl)-6H-[1,3,6,2]-dioxazaborocine top
Crystal data top
C7H14BNO2F(000) = 672
Mr = 155.00Dx = 1.231 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 21.1480 (17) ÅCell parameters from 6734 reflections
b = 8.5399 (11) Åθ = 4.1–26.2°
c = 9.4229 (10) ŵ = 0.09 mm1
β = 100.524 (7)°T = 100 K
V = 1673.2 (3) Å3Needle, colorless
Z = 80.40 × 0.10 × 0.07 mm
Data collection top
Nonius Kappa-CCD
diffractometer
1668 independent reflections
Radiation source: fine-focus sealed tube978 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.138
Detector resolution: 9 pixels mm-1θmax = 26.2°, θmin = 4.1°
ϕ scans and ω scans with κ offsetsh = 2626
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
k = 1010
Tmin = 0.966, Tmax = 0.994l = 1111
6735 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0903P)2]
where P = (Fo2 + 2Fc2)/3
1668 reflections(Δ/σ)max < 0.001
101 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C7H14BNO2V = 1673.2 (3) Å3
Mr = 155.00Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.1480 (17) ŵ = 0.09 mm1
b = 8.5399 (11) ÅT = 100 K
c = 9.4229 (10) Å0.40 × 0.10 × 0.07 mm
β = 100.524 (7)°
Data collection top
Nonius Kappa-CCD
diffractometer
1668 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
978 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.994Rint = 0.138
6735 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.176H-atom parameters constrained
S = 0.99Δρmax = 0.28 e Å3
1668 reflectionsΔρmin = 0.33 e Å3
101 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
xyzUiso*/Ueq
O10.41836 (8)0.0141 (2)0.5642 (2)0.0274 (5)
O20.30289 (9)0.0089 (3)0.4862 (2)0.0316 (6)
N10.37166 (10)0.0895 (3)0.3277 (2)0.0260 (6)
H1C0.37600.04620.23950.031*
C10.36857 (13)0.2228 (3)0.3826 (3)0.0303 (7)
H1A0.41160.23890.35750.036*
H1B0.33610.23310.29300.036*
C20.35697 (13)0.3458 (4)0.4873 (3)0.0310 (7)
H2A0.31340.36490.49470.037*
C30.40050 (15)0.4301 (4)0.5700 (4)0.0393 (8)
H3A0.44480.41560.56680.047*
H3B0.38790.50580.63320.047*
C40.43536 (13)0.1462 (4)0.5535 (3)0.0299 (7)
H4A0.40520.21480.59350.036*
H4B0.47950.16570.60650.036*
C50.43104 (12)0.1760 (4)0.3935 (3)0.0273 (7)
H5A0.46920.13440.35910.033*
H5B0.42690.28930.37130.033*
C60.26518 (13)0.0741 (4)0.3716 (3)0.0336 (8)
H6A0.24460.00100.29550.040*
H6B0.23120.13460.40670.040*
C70.31068 (12)0.1828 (4)0.3135 (3)0.0283 (7)
H7A0.31760.28030.37100.034*
H7B0.29400.20990.21140.034*
B10.36479 (14)0.0496 (4)0.4468 (4)0.0271 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0306 (10)0.0247 (12)0.0270 (11)0.0029 (8)0.0056 (8)0.0009 (9)
O20.0298 (11)0.0362 (13)0.0306 (12)0.0033 (8)0.0099 (8)0.0060 (10)
N10.0287 (12)0.0253 (15)0.0251 (14)0.0000 (10)0.0078 (9)0.0003 (10)
C10.0314 (15)0.0296 (18)0.0311 (17)0.0050 (12)0.0092 (12)0.0019 (14)
C20.0350 (15)0.0248 (17)0.0345 (17)0.0033 (13)0.0100 (12)0.0026 (14)
C30.0457 (18)0.0278 (19)0.046 (2)0.0017 (14)0.0117 (15)0.0001 (15)
C40.0326 (15)0.0269 (18)0.0299 (17)0.0027 (12)0.0052 (12)0.0012 (13)
C50.0242 (14)0.0276 (17)0.0308 (16)0.0028 (12)0.0071 (11)0.0015 (13)
C60.0314 (15)0.0363 (19)0.0336 (18)0.0003 (13)0.0073 (12)0.0041 (14)
C70.0316 (14)0.0257 (17)0.0284 (16)0.0032 (12)0.0079 (11)0.0021 (12)
B10.0271 (17)0.028 (2)0.0261 (18)0.0007 (13)0.0046 (13)0.0061 (14)
Geometric parameters (Å, º) top
O1—C41.424 (4)C2—H2A0.9500
O1—B11.463 (4)C3—H3A0.9500
O2—C61.411 (3)C3—H3B0.9500
O2—B11.466 (4)C4—C51.515 (4)
N1—C51.491 (3)C4—H4A0.9900
N1—C71.501 (3)C4—H4B0.9900
N1—B11.659 (4)C5—H5A0.9900
N1—H1C0.9300C5—H5B0.9900
C1—C21.492 (4)C6—C71.510 (4)
C1—B11.606 (4)C6—H6A0.9900
C1—H1A0.9900C6—H6B0.9900
C1—H1B0.9900C7—H7A0.9900
C2—C31.308 (4)C7—H7B0.9900
C4—O1—B1108.4 (2)H4A—C4—H4B108.8
C6—O2—B1109.3 (2)N1—C5—C4102.9 (2)
C5—N1—C7114.8 (2)N1—C5—H5A111.2
C5—N1—B1104.16 (19)C4—C5—H5A111.2
C7—N1—B1105.11 (19)N1—C5—H5B111.2
C5—N1—H1C110.8C4—C5—H5B111.2
C7—N1—H1C110.8H5A—C5—H5B109.1
B1—N1—H1C110.8O2—C6—C7106.1 (2)
C2—C1—B1112.0 (2)O2—C6—H6A110.5
C2—C1—H1A109.2C7—C6—H6A110.5
B1—C1—H1A109.2O2—C6—H6B110.5
C2—C1—H1B109.2C7—C6—H6B110.5
B1—C1—H1B109.2H6A—C6—H6B108.7
H1A—C1—H1B107.9N1—C7—C6103.6 (2)
C3—C2—C1126.8 (3)N1—C7—H7A111.0
C3—C2—H2A116.6C6—C7—H7A111.0
C1—C2—H2A116.6N1—C7—H7B111.0
C2—C3—H3A120.0C6—C7—H7B111.0
C2—C3—H3B120.0H7A—C7—H7B109.0
H3A—C3—H3B120.0O1—B1—O2111.3 (2)
O1—C4—C5105.2 (2)O1—B1—C1113.0 (2)
O1—C4—H4A110.7O2—B1—C1115.0 (2)
C5—C4—H4A110.7O1—B1—N1102.2 (2)
O1—C4—H4B110.7O2—B1—N1101.2 (2)
C5—C4—H4B110.7C1—B1—N1112.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.932.042.907 (3)155
Symmetry code: (i) x, y, z1/2.

Experimental details

Crystal data
Chemical formulaC7H14BNO2
Mr155.00
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)21.1480 (17), 8.5399 (11), 9.4229 (10)
β (°) 100.524 (7)
V3)1673.2 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.10 × 0.07
Data collection
DiffractometerNonius Kappa-CCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.966, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
6735, 1668, 978
Rint0.138
(sin θ/λ)max1)0.621
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.176, 0.99
No. of reflections1668
No. of parameters101
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.33

Computer programs: COLLECT (Nonius, 1997-2001), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
O1—B11.463 (4)N1—B11.659 (4)
O2—B11.466 (4)C1—B11.606 (4)
O1—B1—O2111.3 (2)O2—B1—N1101.2 (2)
O1—B1—N1102.2 (2)C1—B1—N1112.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.932.042.907 (3)155.4
Symmetry code: (i) x, y, z1/2.
 

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