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The title compound, C9H22BP, and its coupling product, C16H38B2P2, were synthesized and their crystal structures analyzed by X-ray diffraction. The molecular structures clearly explain the stereoselective reaction pathways leading to the products. The average P-B distance and C-P-B angle are 1.929 Å and 114°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004066/oa1100sup1.cif
Contains datablocks global, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004066/oa1100IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004066/oa1100IIIsup3.hkl
Contains datablock III

CCDC references: 146075; 146076

Computing details top

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(II) top
Crystal data top
C9H22BPMelting point = 301–303 K
Mr = 172.06Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, Pna21Cell parameters from 25 reflections
a = 12.52 (2) Åθ = 7.3–34.7°
b = 6.944 (1) ŵ = 1.69 mm1
c = 12.919 (1) ÅT = 123 K
V = 1123 (1) Å3Prismatic, colorless
Z = 40.40 × 0.30 × 0.30 mm
Dx = 1.017 Mg m3
Data collection top
Rigaku AFC7S
diffractometer
Rint = 0.02
ω–2θ scansθmax = 67.6°
Absorption correction: ψ scan
(North et al., 1968)
h = 150
Tmin = 0.576, Tmax = 0.602k = 08
1056 measured reflectionsl = 015
1056 independent reflections3 standard reflections every 150 reflections
1030 reflections with F2 > 2.0σ(F2) intensity decay: 1.0%
Refinement top
Refinement on F w = 1/[σ2(Fo) + 0.00022|Fo|2]
R[F2 > 2σ(F2)] = 0.039(Δ/σ)max = 0.012
wR(F2) = 0.050Δρmax = 0.40 e Å3
S = 1.91Δρmin = 0.34 e Å3
1030 reflectionsExtinction correction: Zachariasen (1967) type 2 Gaussian isotropic
102 parametersExtinction coefficient: 0.035 (7)
H-atom parameters not refined
Special details top

Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P0.81816 (4)0.17946 (7)0.0538 (7)0.0193 (1)
C10.9571 (2)0.1250 (3)0.0168 (7)0.0217 (5)
C20.9652 (2)0.2016 (4)0.0945 (7)0.0291 (6)
C30.9051 (2)0.3912 (4)0.0990 (6)0.0342 (6)
C40.7956 (2)0.3588 (4)0.0476 (7)0.0297 (6)
C50.8211 (2)0.2990 (3)0.1818 (7)0.0248 (6)
C60.8719 (2)0.1596 (4)0.2585 (7)0.0350 (7)
C70.7054 (2)0.3439 (4)0.2137 (7)0.0342 (7)
C80.8852 (2)0.4881 (4)0.1793 (7)0.0355 (7)
C90.9882 (2)0.0858 (3)0.0285 (7)0.0321 (6)
B0.7184 (2)0.0311 (4)0.0452 (7)0.0313 (6)
H11.00340.19940.05870.0255*
H20.93550.11060.14230.0364*
H31.03960.21870.11300.0364*
H40.89730.43260.16990.0414*
H50.94480.48930.06330.0414*
H60.76770.47730.01860.0370*
H70.74370.31370.09700.0370*
H80.94440.13050.23430.0449*
H90.87680.21390.32450.0449*
H100.83370.04230.26000.0449*
H110.66590.23030.21460.0423*
H120.70590.40410.27930.0423*
H130.67510.43210.16390.0423*
H140.88740.54720.24460.0434*
H150.85720.57620.12920.0434*
H160.95850.45950.15830.0434*
H170.64730.01290.05240.0404*
H180.72580.09610.01970.0404*
H190.73260.12370.09930.0404*
H200.98070.12550.09880.0400*
H211.06020.10570.00730.0400*
H220.94270.16540.01350.0400*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0193 (3)0.0217 (3)0.0169 (3)0.0019 (2)0.0007 (3)0.0007 (3)
C10.0205 (9)0.0217 (9)0.023 (1)0.0036 (8)0.0017 (9)0.0020 (9)
C20.030 (1)0.037 (1)0.020 (1)0.0064 (9)0.007 (1)0.003 (1)
C30.042 (1)0.036 (1)0.025 (1)0.004 (1)0.006 (1)0.010 (1)
C40.034 (1)0.034 (1)0.022 (1)0.003 (1)0.005 (1)0.007 (1)
C50.029 (1)0.028 (1)0.018 (1)0.0031 (8)0.0002 (9)0.0018 (9)
C60.040 (1)0.047 (2)0.018 (1)0.009 (1)0.002 (1)0.006 (1)
C70.031 (1)0.046 (1)0.026 (1)0.007 (1)0.005 (1)0.006 (1)
C80.041 (1)0.031 (1)0.034 (1)0.005 (1)0.003 (1)0.012 (1)
C90.030 (1)0.0248 (10)0.041 (2)0.0024 (9)0.005 (1)0.000 (1)
B0.025 (1)0.028 (1)0.041 (2)0.0067 (9)0.005 (1)0.005 (2)
Geometric parameters (Å, º) top
P—C11.843 (4)C2—C31.518 (5)
P—C41.829 (4)C3—C41.539 (5)
P—C51.851 (4)C5—C61.523 (5)
P—B1.926 (4)C5—C71.538 (5)
C1—C21.536 (5)C5—C81.539 (5)
C1—C91.523 (4)
C1—P—C495.7 (2)C1—C2—C3107.6 (3)
C1—P—C5107.8 (2)C2—C3—C4107.4 (3)
C1—P—B116.2 (2)P—C4—C3105.7 (2)
C4—P—C5109.8 (2)P—C5—C6107.7 (2)
C4—P—B112.0 (2)P—C5—C7108.2 (2)
C5—P—B113.9 (2)P—C5—C8111.9 (3)
P—C1—C2103.5 (2)C6—C5—C7110.3 (3)
P—C1—C9114.4 (2)C6—C5—C8109.8 (3)
C2—C1—C9114.1 (3)C7—C5—C8108.9 (3)
P—C1—C2—C340.3 (3)C3—C4—P—C5103.4 (3)
P—C4—C3—C232.5 (3)C3—C4—P—B129.0 (3)
C1—P—C4—C37.8 (3)C4—P—C1—C9143.1 (3)
C1—P—C5—C660.4 (3)C4—P—C5—C6163.4 (3)
C1—P—C5—C7179.6 (2)C4—P—C5—C777.3 (3)
C1—P—C5—C860.4 (3)C4—P—C5—C842.7 (3)
C1—C2—C3—C448.5 (4)C5—P—C1—C9104.1 (3)
C2—C1—P—C418.2 (2)C6—C5—P—B70.1 (3)
C2—C1—P—C5131.1 (2)C7—C5—P—B49.2 (3)
C2—C1—P—B99.8 (3)C8—C5—P—B169.2 (2)
C3—C2—C1—C9165.3 (3)C9—C1—P—B25.1 (4)
(III) top
Crystal data top
C16H38B2P2Dx = 1.017 Mg m3
Mr = 314.04Cu Kα radiation, λ = 1.5418 Å
Monoclinic, C2/cCell parameters from 20 reflections
a = 10.346 (1) Åθ = 22.1–24.7°
b = 9.796 (2) ŵ = 1.82 mm1
c = 20.597 (1) ÅT = 296 K
β = 100.805 (8)°Prismatic, colorless
V = 2050.5 (4) Å30.48 × 0.30 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC5S
diffractometer
Rint = 0.022
ω–2θ scansθmax = 67.6°
Absorption correction: ψ scan
(North et al., 1968)
h = 012
Tmin = 0.517, Tmax = 0.695k = 011
1945 measured reflectionsl = 2424
1839 independent reflections3 standard reflections every 150 reflections
1376 reflections with F2 > 2.0σ(F2) intensity decay: 0.8%
Refinement top
Refinement on F w = 1/[σ2(Fo) + 0.00022|Fo|2]
R[F2 > 2σ(F2)] = 0.048(Δ/σ)max = 0.0.1
wR(F2) = 0.058Δρmax = 0.23 e Å3
S = 1.79Δρmin = 0.18 e Å3
1423 reflectionsExtinction correction: Zachariasen (1967) type 2 Gaussian isotropic
92 parametersExtinction coefficient: 0.086 (5)
H-atom parameters not refined
Special details top

Refinement. Refinement using reflections with F2 > 1.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P0.66094 (7)0.29673 (8)0.59162 (4)0.0462 (2)
C10.6933 (2)0.2183 (3)0.5141 (1)0.0389 (7)
C20.5587 (3)0.2298 (3)0.4673 (1)0.0485 (8)
C30.4512 (3)0.1997 (3)0.5066 (2)0.0568 (9)
C40.4812 (3)0.2888 (3)0.5677 (2)0.0592 (9)
C50.7094 (3)0.1790 (4)0.6625 (1)0.0608 (10)
C60.6601 (5)0.2441 (6)0.7210 (2)0.120 (2)
C70.8565 (4)0.1658 (5)0.6803 (2)0.098 (1)
C80.6471 (4)0.0393 (4)0.6490 (2)0.104 (2)
B0.7180 (4)0.4822 (4)0.6071 (2)0.072 (1)
H10.68280.52120.64260.0872*
H20.81340.48540.61980.0872*
H30.69320.53630.56880.0872*
H40.71840.11140.52390.0564*
H50.55320.16670.43150.0592*
H60.54690.32000.44950.0592*
H70.45340.10480.51840.0680*
H80.36670.21990.48110.0680*
H90.44560.37780.55870.0721*
H100.44420.24990.60290.0721*
H110.55390.04480.63640.1239*
H120.67910.00430.61190.1239*
H130.66910.02030.68580.1239*
H140.56480.25700.71000.1503*
H150.69710.33420.73030.1503*
H160.67920.19100.75950.1503*
H170.89690.25150.68910.1203*
H180.88920.12360.64420.1203*
H190.88030.10790.71810.1203*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0395 (4)0.0523 (4)0.0485 (4)0.0033 (4)0.0127 (3)0.0061 (4)
C10.033 (1)0.039 (1)0.045 (1)0.001 (1)0.008 (1)0.002 (1)
C20.036 (1)0.057 (2)0.052 (2)0.004 (1)0.007 (1)0.007 (1)
C30.032 (1)0.068 (2)0.070 (2)0.003 (1)0.010 (1)0.004 (2)
C40.038 (1)0.075 (2)0.068 (2)0.005 (2)0.020 (1)0.003 (2)
C50.055 (2)0.081 (2)0.046 (2)0.009 (2)0.007 (1)0.007 (2)
C60.137 (4)0.173 (5)0.059 (2)0.004 (4)0.043 (3)0.008 (3)
C70.063 (2)0.152 (4)0.072 (2)0.008 (2)0.006 (2)0.045 (3)
C80.110 (3)0.094 (3)0.094 (3)0.032 (3)0.016 (3)0.042 (3)
B0.072 (3)0.055 (2)0.094 (3)0.006 (2)0.027 (2)0.022 (2)
Geometric parameters (Å, º) top
P—C11.859 (3)C2—C31.522 (4)
P—C41.834 (3)C3—C41.516 (4)
P—C51.854 (3)C5—C61.534 (5)
P—B1.919 (4)C5—C71.503 (5)
C1—C1i1.534 (4)C5—C81.515 (5)
C1—C21.542 (4)
C1—P—C495.1 (1)C1—C2—C3108.6 (2)
C1—P—C5110.7 (1)C2—C3—C4105.9 (2)
C1—P—B115.8 (2)P—C4—C3106.7 (2)
C4—P—C5107.2 (1)P—C5—C6106.2 (3)
C4—P—B110.5 (2)P—C5—C7111.0 (2)
C5—P—B115.4 (2)P—C5—C8112.0 (2)
P—C1—C1i115.5 (2)C6—C5—C7108.3 (3)
P—C1—C2102.7 (2)C6—C5—C8109.1 (3)
C1—C1i—C2113.6 (3)C7—C5—C8110.1 (3)
P—C1—C1i—Pi180.0C2—C1—P—C415.6 (2)
P—C1—C1i—C2i61.7 (3)C2—C1—P—C5126.2 (2)
P—C1—C2—C339.4 (3)C2—C1—P—B100.0 (2)
P—C4—C3—C235.6 (3)C2—C1—C1i—C2i180.0
C1—P—C4—C311.3 (2)C3—C4—P—C5102.2 (2)
C1—P—C5—C6171.8 (3)C3—C4—P—B131.3 (2)
C1—P—C5—C770.7 (3)C4—P—C5—C669.3 (3)
C1—P—C5—C852.8 (3)C4—P—C5—C7173.2 (3)
C1—C1i—Pi—C4i139.8 (3)C4—P—C5—C849.7 (3)
C1—C1i—Pi—C5i109.7 (3)C6—C5—P—B54.2 (3)
C1—C1i—Pi—Bi24.1 (3)C7—C5—P—B63.3 (3)
C1—C1i—C2i—C3i164.9 (3)C8—C5—P—B173.2 (3)
C1—C2—C3—C450.1 (3)
Symmetry code: (i) x+3/2, y+1/2, z+1.
 

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