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The title compound [alternative name: 8-methyl-8-aza­bi­cyclo­[3.2.1]­octan-3-yl­methyl p-toluene­sulfonate(N8-B)-bor­ane], C16H26BNO3S, has the tosyl­oxy­methyl substituent in an endo position. The BH3 group is equatorial and the (N-bonded) methyl group is axial, relative to the six-membered heterocycle. The N-B bond of 1.649 (8) Å is one of the longest known.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013019/qa0392sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013019/qa0392Isup2.hkl
Contains datablock I

CCDC reference: 153941

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL.

3α-Tosyloxymethyltropane(N8—B)–borane top
Crystal data top
C16H26BNO3SDx = 1.230 Mg m3
Mr = 323.25Melting point: 113.8–116.5 ° C K
Orthorhombic, Pna21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 21.443 (2) Åθ = 20.5–25.2°
b = 7.959 (1) ŵ = 1.73 mm1
c = 10.224 (2) ÅT = 293 K
V = 1744.9 (4) Å3Prism, colourless
Z = 40.28 × 0.22 × 0.11 mm
F(000) = 696
Data collection top
Rigaku AFC-6S four-circle
diffractometer
1613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 75°, θmin = 4.1°
2θ/ω scansh = 1626
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)
k = 69
Tmin = 0.726, Tmax = 0.837l = 812
2243 measured reflections3 standard reflections every 147 reflections
2157 independent reflections intensity decay: 0.8%
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0473P)2 + 0.4507P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.21 e Å3
2157 reflectionsΔρmin = 0.17 e Å3
208 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00081 (14)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.35 (3)
Special details top

Experimental. The crystal was a racemic twin with the component contributions of 0.65 (3) and 0.35 (3).

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 on F2 for ALL reflections. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_gt etc. and is not relevant to the choice of reflections for refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.62305 (5)0.40959 (14)0.49106 (13)0.0519 (3)
O10.55683 (14)0.4624 (4)0.4392 (3)0.0549 (9)
O20.6527 (2)0.3351 (4)0.3808 (4)0.0656 (10)
O30.6162 (2)0.3152 (5)0.6094 (4)0.0647 (10)
N0.3988 (2)0.9398 (4)0.5051 (4)0.0487 (10)
C10.3977 (2)0.8095 (6)0.6114 (5)0.0490 (12)
H10.3598 (2)0.8212 (6)0.6641 (5)0.059*
C20.4024 (2)0.6322 (6)0.5566 (6)0.0543 (13)
H210.3641 (2)0.6071 (6)0.5100 (6)0.071*
H220.4055 (2)0.5540 (6)0.6290 (6)0.071*
C30.4580 (2)0.6017 (6)0.4633 (5)0.0500 (13)
H30.4436 (2)0.5223 (6)0.3966 (5)0.060*
C40.4783 (2)0.7622 (6)0.3904 (5)0.0555 (13)
H410.5225 (2)0.7541 (6)0.3716 (5)0.072*
H420.4564 (2)0.7666 (6)0.3074 (5)0.072*
C50.4665 (2)0.9258 (6)0.4631 (5)0.0546 (14)
H50.4780 (2)1.0218 (6)0.4082 (5)0.066*
C60.5006 (2)0.9343 (7)0.5936 (5)0.0615 (15)
H610.5103 (2)1.0496 (7)0.6165 (5)0.080*
H620.5390 (2)0.8701 (7)0.5906 (5)0.080*
C70.4546 (3)0.8577 (7)0.6921 (5)0.0597 (14)
H710.4726 (3)0.7594 (7)0.7338 (5)0.078*
H720.4436 (3)0.9387 (7)0.7591 (5)0.078*
C80.3543 (3)0.9034 (7)0.3959 (6)0.076 (2)
H810.3609 (12)0.982 (3)0.3263 (17)0.114 (14)*
H820.3122 (3)0.913 (5)0.4271 (11)0.114 (14)*
H830.3612 (12)0.7914 (19)0.364 (3)0.114 (14)*
C90.5105 (2)0.5163 (6)0.5362 (5)0.0560 (14)
H910.5293 (2)0.5937 (6)0.5980 (5)0.073*
H920.4948 (2)0.4200 (6)0.5841 (5)0.073*
C100.7495 (3)1.0692 (7)0.6108 (7)0.082 (2)
H1010.7187 (4)1.1483 (19)0.640 (4)0.137 (16)*
H1020.7693 (18)1.111 (3)0.5332 (13)0.137 (16)*
H1030.7802 (15)1.0534 (14)0.678 (3)0.137 (16)*
C110.6586 (2)0.6013 (6)0.5268 (5)0.0476 (12)
C120.6851 (2)0.6273 (7)0.6478 (5)0.0589 (14)
H120.6829 (2)0.5447 (7)0.7120 (5)0.071*
C130.7151 (3)0.7806 (7)0.6730 (6)0.064 (2)
H130.7333 (3)0.7988 (7)0.7543 (6)0.077*
C140.7180 (2)0.9020 (8)0.5810 (6)0.0612 (15)
C150.6919 (2)0.8745 (7)0.4600 (6)0.061 (2)
H150.6940 (2)0.9585 (7)0.3969 (6)0.074*
C160.6628 (2)0.7257 (7)0.4310 (5)0.0581 (14)
H160.6458 (2)0.7079 (7)0.3484 (5)0.070*
B0.3812 (3)1.1297 (9)0.5579 (8)0.075 (2)
H1B0.4151 (12)1.1668 (19)0.646 (3)0.077 (9)*
H2B0.3286 (12)1.1315 (13)0.595 (3)0.077 (9)*
H3B0.3871 (12)1.228 (3)0.471 (2)0.077 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0494 (6)0.0530 (6)0.0534 (7)0.0071 (6)0.0019 (7)0.0057 (8)
O10.047 (2)0.063 (2)0.054 (2)0.004 (2)0.003 (2)0.013 (2)
O20.062 (2)0.071 (2)0.063 (2)0.007 (2)0.004 (2)0.022 (2)
O30.067 (2)0.055 (2)0.072 (3)0.006 (2)0.001 (2)0.014 (2)
N0.050 (2)0.050 (2)0.047 (3)0.003 (2)0.001 (2)0.002 (2)
C10.048 (3)0.058 (3)0.041 (3)0.005 (2)0.002 (2)0.005 (3)
C20.043 (2)0.053 (3)0.067 (3)0.007 (2)0.002 (3)0.003 (3)
C30.046 (2)0.056 (3)0.048 (4)0.003 (2)0.002 (2)0.004 (3)
C40.056 (3)0.069 (3)0.041 (3)0.003 (3)0.010 (3)0.000 (3)
C50.062 (3)0.052 (3)0.050 (4)0.006 (2)0.011 (3)0.007 (3)
C60.054 (3)0.058 (3)0.073 (4)0.007 (3)0.004 (3)0.012 (3)
C70.061 (3)0.078 (4)0.040 (3)0.001 (3)0.001 (3)0.001 (3)
C80.064 (3)0.095 (5)0.068 (4)0.020 (3)0.015 (3)0.001 (4)
C90.049 (3)0.058 (3)0.061 (4)0.007 (2)0.008 (3)0.005 (3)
C100.055 (3)0.057 (4)0.136 (6)0.003 (3)0.004 (4)0.023 (4)
C110.043 (2)0.051 (3)0.048 (4)0.004 (2)0.004 (2)0.004 (3)
C120.059 (3)0.067 (4)0.050 (3)0.006 (3)0.001 (3)0.007 (3)
C130.068 (4)0.064 (4)0.060 (4)0.008 (3)0.017 (3)0.016 (3)
C140.036 (3)0.064 (4)0.084 (4)0.003 (3)0.000 (3)0.016 (4)
C150.060 (3)0.060 (3)0.064 (4)0.003 (3)0.005 (3)0.008 (3)
C160.057 (3)0.068 (4)0.049 (3)0.000 (3)0.002 (3)0.002 (3)
B0.084 (4)0.059 (4)0.083 (5)0.019 (4)0.009 (5)0.000 (4)
Geometric parameters (Å, º) top
S—O21.424 (4)C3—C91.513 (6)
S—O31.432 (4)C3—C41.541 (6)
S—O11.573 (3)C4—C51.520 (6)
S—C111.745 (5)C5—C61.523 (7)
O1—C91.467 (5)C6—C71.536 (7)
N—C81.497 (7)C10—C141.523 (7)
N—C11.502 (6)C11—C121.376 (7)
N—C51.518 (6)C11—C161.396 (7)
N—B1.649 (8)C12—C131.403 (7)
C1—C21.522 (6)C13—C141.350 (8)
C1—C71.523 (7)C14—C151.375 (7)
C2—C31.545 (6)C15—C161.372 (7)
O2—S—O3119.8 (2)C4—C3—C2112.7 (4)
O2—S—O1104.4 (2)C5—C4—C3115.3 (4)
O3—S—O1109.4 (2)N—C5—C4111.1 (4)
O2—S—C11109.6 (2)N—C5—C6102.0 (4)
O3—S—C11109.0 (2)C4—C5—C6112.7 (4)
O1—S—C11103.4 (2)C5—C6—C7104.4 (4)
C9—O1—S117.5 (3)C1—C7—C6105.0 (4)
C8—N—C1113.3 (4)O1—C9—C3107.7 (4)
C8—N—C5112.6 (4)C12—C11—C16119.9 (5)
C1—N—C599.7 (3)C12—C11—S120.0 (4)
C8—N—B106.0 (4)C16—C11—S120.1 (4)
C1—N—B113.1 (4)C11—C12—C13119.0 (5)
C5—N—B112.3 (4)C14—C13—C12121.0 (5)
N—C1—C2111.9 (4)C13—C14—C15119.6 (5)
N—C1—C7101.9 (4)C13—C14—C10120.4 (6)
C2—C1—C7112.3 (4)C15—C14—C10120.0 (6)
C1—C2—C3115.0 (4)C16—C15—C14121.2 (5)
C9—C3—C4113.6 (4)C15—C16—C11119.3 (5)
C9—C3—C2110.0 (4)
 

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