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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
CCDC references: 146075; 146076
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.
Crystal data top
C9H22BP | Melting point = 301–303 K |
Mr = 172.06 | Cu Kα radiation, λ = 1.5418 Å |
Orthorhombic, Pna21 | Cell parameters from 25 reflections |
a = 12.52 (2) Å | θ = 7.3–34.7° |
b = 6.944 (1) Å | µ = 1.69 mm−1 |
c = 12.919 (1) Å | T = 123 K |
V = 1123 (1) Å3 | Prismatic, colorless |
Z = 4 | 0.40 × 0.30 × 0.30 mm |
Dx = 1.017 Mg m−3 | |
Data collection top
Rigaku AFC7S diffractometer | Rint = 0.02 |
ω–2θ scans | θmax = 67.6° |
Absorption correction: ψ scan (North et al., 1968) | h = −15→0 |
Tmin = 0.576, Tmax = 0.602 | k = 0→8 |
1056 measured reflections | l = 0→15 |
1056 independent reflections | 3 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) = 0.050 | Δρmax = 0.40 e Å−3 |
S = 1.91 | Δρmin = −0.34 e Å−3 |
1030 reflections | Extinction correction: Zachariasen (1967) type 2 Gaussian isotropic |
102 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
P | 0.81816 (4) | 0.17946 (7) | 0.0538 (7) | 0.0193 (1) | |
C1 | 0.9571 (2) | 0.1250 (3) | 0.0168 (7) | 0.0217 (5) | |
C2 | 0.9652 (2) | 0.2016 (4) | −0.0945 (7) | 0.0291 (6) | |
C3 | 0.9051 (2) | 0.3912 (4) | −0.0990 (6) | 0.0342 (6) | |
C4 | 0.7956 (2) | 0.3588 (4) | −0.0476 (7) | 0.0297 (6) | |
C5 | 0.8211 (2) | 0.2990 (3) | 0.1818 (7) | 0.0248 (6) | |
C6 | 0.8719 (2) | 0.1596 (4) | 0.2585 (7) | 0.0350 (7) | |
C7 | 0.7054 (2) | 0.3439 (4) | 0.2137 (7) | 0.0342 (7) | |
C8 | 0.8852 (2) | 0.4881 (4) | 0.1793 (7) | 0.0355 (7) | |
C9 | 0.9882 (2) | −0.0858 (3) | 0.0285 (7) | 0.0321 (6) | |
B | 0.7184 (2) | −0.0311 (4) | 0.0452 (7) | 0.0313 (6) | |
H1 | 1.0034 | 0.1994 | 0.0587 | 0.0255* | |
H2 | 0.9355 | 0.1106 | −0.1423 | 0.0364* | |
H3 | 1.0396 | 0.2187 | −0.1130 | 0.0364* | |
H4 | 0.8973 | 0.4326 | −0.1699 | 0.0414* | |
H5 | 0.9448 | 0.4893 | −0.0633 | 0.0414* | |
H6 | 0.7677 | 0.4773 | −0.0186 | 0.0370* | |
H7 | 0.7437 | 0.3137 | −0.0970 | 0.0370* | |
H8 | 0.9444 | 0.1305 | 0.2343 | 0.0449* | |
H9 | 0.8768 | 0.2139 | 0.3245 | 0.0449* | |
H10 | 0.8337 | 0.0423 | 0.2600 | 0.0449* | |
H11 | 0.6659 | 0.2303 | 0.2146 | 0.0423* | |
H12 | 0.7059 | 0.4041 | 0.2793 | 0.0423* | |
H13 | 0.6751 | 0.4321 | 0.1639 | 0.0423* | |
H14 | 0.8874 | 0.5472 | 0.2446 | 0.0434* | |
H15 | 0.8572 | 0.5762 | 0.1292 | 0.0434* | |
H16 | 0.9585 | 0.4595 | 0.1583 | 0.0434* | |
H17 | 0.6473 | 0.0129 | 0.0524 | 0.0404* | |
H18 | 0.7258 | −0.0961 | −0.0197 | 0.0404* | |
H19 | 0.7326 | −0.1237 | 0.0993 | 0.0404* | |
H20 | 0.9807 | −0.1255 | 0.0988 | 0.0400* | |
H21 | 1.0602 | −0.1057 | 0.0073 | 0.0400* | |
H22 | 0.9427 | −0.1654 | −0.0135 | 0.0400* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P | 0.0193 (3) | 0.0217 (3) | 0.0169 (3) | −0.0019 (2) | 0.0007 (3) | −0.0007 (3) |
C1 | 0.0205 (9) | 0.0217 (9) | 0.023 (1) | −0.0036 (8) | 0.0017 (9) | −0.0020 (9) |
C2 | 0.030 (1) | 0.037 (1) | 0.020 (1) | −0.0064 (9) | 0.007 (1) | −0.003 (1) |
C3 | 0.042 (1) | 0.036 (1) | 0.025 (1) | −0.004 (1) | 0.006 (1) | 0.010 (1) |
C4 | 0.034 (1) | 0.034 (1) | 0.022 (1) | 0.003 (1) | −0.005 (1) | 0.007 (1) |
C5 | 0.029 (1) | 0.028 (1) | 0.018 (1) | 0.0031 (8) | 0.0002 (9) | −0.0018 (9) |
C6 | 0.040 (1) | 0.047 (2) | 0.018 (1) | 0.009 (1) | −0.002 (1) | 0.006 (1) |
C7 | 0.031 (1) | 0.046 (1) | 0.026 (1) | 0.007 (1) | 0.005 (1) | −0.006 (1) |
C8 | 0.041 (1) | 0.031 (1) | 0.034 (1) | −0.005 (1) | −0.003 (1) | −0.012 (1) |
C9 | 0.030 (1) | 0.0248 (10) | 0.041 (2) | 0.0024 (9) | 0.005 (1) | 0.000 (1) |
B | 0.025 (1) | 0.028 (1) | 0.041 (2) | −0.0067 (9) | 0.005 (1) | −0.005 (2) |
Geometric parameters (Å, º) top
P—C1 | 1.843 (4) | C2—C3 | 1.518 (5) |
P—C4 | 1.829 (4) | C3—C4 | 1.539 (5) |
P—C5 | 1.851 (4) | C5—C6 | 1.523 (5) |
P—B | 1.926 (4) | C5—C7 | 1.538 (5) |
C1—C2 | 1.536 (5) | C5—C8 | 1.539 (5) |
C1—C9 | 1.523 (4) | | |
| | | |
C1—P—C4 | 95.7 (2) | C1—C2—C3 | 107.6 (3) |
C1—P—C5 | 107.8 (2) | C2—C3—C4 | 107.4 (3) |
C1—P—B | 116.2 (2) | P—C4—C3 | 105.7 (2) |
C4—P—C5 | 109.8 (2) | P—C5—C6 | 107.7 (2) |
C4—P—B | 112.0 (2) | P—C5—C7 | 108.2 (2) |
C5—P—B | 113.9 (2) | P—C5—C8 | 111.9 (3) |
P—C1—C2 | 103.5 (2) | C6—C5—C7 | 110.3 (3) |
P—C1—C9 | 114.4 (2) | C6—C5—C8 | 109.8 (3) |
C2—C1—C9 | 114.1 (3) | C7—C5—C8 | 108.9 (3) |
| | | |
P—C1—C2—C3 | 40.3 (3) | C3—C4—P—C5 | 103.4 (3) |
P—C4—C3—C2 | 32.5 (3) | C3—C4—P—B | −129.0 (3) |
C1—P—C4—C3 | −7.8 (3) | C4—P—C1—C9 | −143.1 (3) |
C1—P—C5—C6 | −60.4 (3) | C4—P—C5—C6 | −163.4 (3) |
C1—P—C5—C7 | −179.6 (2) | C4—P—C5—C7 | 77.3 (3) |
C1—P—C5—C8 | 60.4 (3) | C4—P—C5—C8 | −42.7 (3) |
C1—C2—C3—C4 | −48.5 (4) | C5—P—C1—C9 | 104.1 (3) |
C2—C1—P—C4 | −18.2 (2) | C6—C5—P—B | 70.1 (3) |
C2—C1—P—C5 | −131.1 (2) | C7—C5—P—B | −49.2 (3) |
C2—C1—P—B | 99.8 (3) | C8—C5—P—B | −169.2 (2) |
C3—C2—C1—C9 | 165.3 (3) | C9—C1—P—B | −25.1 (4) |
Crystal data top
C16H38B2P2 | Dx = 1.017 Mg m−3 |
Mr = 314.04 | Cu Kα radiation, λ = 1.5418 Å |
Monoclinic, C2/c | Cell parameters from 20 reflections |
a = 10.346 (1) Å | θ = 22.1–24.7° |
b = 9.796 (2) Å | µ = 1.82 mm−1 |
c = 20.597 (1) Å | T = 296 K |
β = 100.805 (8)° | Prismatic, colorless |
V = 2050.5 (4) Å3 | 0.48 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Rigaku AFC5S diffractometer | Rint = 0.022 |
ω–2θ scans | θmax = 67.6° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→12 |
Tmin = 0.517, Tmax = 0.695 | k = 0→11 |
1945 measured reflections | l = −24→24 |
1839 independent reflections | 3 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) = 0.058 | Δρmax = 0.23 e Å−3 |
S = 1.79 | Δρmin = −0.18 e Å−3 |
1423 reflections | Extinction correction: Zachariasen (1967) type 2 Gaussian isotropic |
92 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
P | 0.66094 (7) | 0.29673 (8) | 0.59162 (4) | 0.0462 (2) | |
C1 | 0.6933 (2) | 0.2183 (3) | 0.5141 (1) | 0.0389 (7) | |
C2 | 0.5587 (3) | 0.2298 (3) | 0.4673 (1) | 0.0485 (8) | |
C3 | 0.4512 (3) | 0.1997 (3) | 0.5066 (2) | 0.0568 (9) | |
C4 | 0.4812 (3) | 0.2888 (3) | 0.5677 (2) | 0.0592 (9) | |
C5 | 0.7094 (3) | 0.1790 (4) | 0.6625 (1) | 0.0608 (10) | |
C6 | 0.6601 (5) | 0.2441 (6) | 0.7210 (2) | 0.120 (2) | |
C7 | 0.8565 (4) | 0.1658 (5) | 0.6803 (2) | 0.098 (1) | |
C8 | 0.6471 (4) | 0.0393 (4) | 0.6490 (2) | 0.104 (2) | |
B | 0.7180 (4) | 0.4822 (4) | 0.6071 (2) | 0.072 (1) | |
H1 | 0.6828 | 0.5212 | 0.6426 | 0.0872* | |
H2 | 0.8134 | 0.4854 | 0.6198 | 0.0872* | |
H3 | 0.6932 | 0.5363 | 0.5688 | 0.0872* | |
H4 | 0.7184 | 0.1114 | 0.5239 | 0.0564* | |
H5 | 0.5532 | 0.1667 | 0.4315 | 0.0592* | |
H6 | 0.5469 | 0.3200 | 0.4495 | 0.0592* | |
H7 | 0.4534 | 0.1048 | 0.5184 | 0.0680* | |
H8 | 0.3667 | 0.2199 | 0.4811 | 0.0680* | |
H9 | 0.4456 | 0.3778 | 0.5587 | 0.0721* | |
H10 | 0.4442 | 0.2499 | 0.6029 | 0.0721* | |
H11 | 0.5539 | 0.0448 | 0.6364 | 0.1239* | |
H12 | 0.6791 | −0.0043 | 0.6119 | 0.1239* | |
H13 | 0.6691 | −0.0203 | 0.6858 | 0.1239* | |
H14 | 0.5648 | 0.2570 | 0.7100 | 0.1503* | |
H15 | 0.6971 | 0.3342 | 0.7303 | 0.1503* | |
H16 | 0.6792 | 0.1910 | 0.7595 | 0.1503* | |
H17 | 0.8969 | 0.2515 | 0.6891 | 0.1203* | |
H18 | 0.8892 | 0.1236 | 0.6442 | 0.1203* | |
H19 | 0.8803 | 0.1079 | 0.7181 | 0.1203* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P | 0.0395 (4) | 0.0523 (4) | 0.0485 (4) | −0.0033 (4) | 0.0127 (3) | −0.0061 (4) |
C1 | 0.033 (1) | 0.039 (1) | 0.045 (1) | −0.001 (1) | 0.008 (1) | −0.002 (1) |
C2 | 0.036 (1) | 0.057 (2) | 0.052 (2) | −0.004 (1) | 0.007 (1) | −0.007 (1) |
C3 | 0.032 (1) | 0.068 (2) | 0.070 (2) | −0.003 (1) | 0.010 (1) | −0.004 (2) |
C4 | 0.038 (1) | 0.075 (2) | 0.068 (2) | 0.005 (2) | 0.020 (1) | −0.003 (2) |
C5 | 0.055 (2) | 0.081 (2) | 0.046 (2) | −0.009 (2) | 0.007 (1) | 0.007 (2) |
C6 | 0.137 (4) | 0.173 (5) | 0.059 (2) | 0.004 (4) | 0.043 (3) | 0.008 (3) |
C7 | 0.063 (2) | 0.152 (4) | 0.072 (2) | −0.008 (2) | −0.006 (2) | 0.045 (3) |
C8 | 0.110 (3) | 0.094 (3) | 0.094 (3) | −0.032 (3) | −0.016 (3) | 0.042 (3) |
B | 0.072 (3) | 0.055 (2) | 0.094 (3) | −0.006 (2) | 0.027 (2) | −0.022 (2) |
Geometric parameters (Å, º) top
P—C1 | 1.859 (3) | C2—C3 | 1.522 (4) |
P—C4 | 1.834 (3) | C3—C4 | 1.516 (4) |
P—C5 | 1.854 (3) | C5—C6 | 1.534 (5) |
P—B | 1.919 (4) | C5—C7 | 1.503 (5) |
C1—C1i | 1.534 (4) | C5—C8 | 1.515 (5) |
C1—C2 | 1.542 (4) | | |
| | | |
C1—P—C4 | 95.1 (1) | C1—C2—C3 | 108.6 (2) |
C1—P—C5 | 110.7 (1) | C2—C3—C4 | 105.9 (2) |
C1—P—B | 115.8 (2) | P—C4—C3 | 106.7 (2) |
C4—P—C5 | 107.2 (1) | P—C5—C6 | 106.2 (3) |
C4—P—B | 110.5 (2) | P—C5—C7 | 111.0 (2) |
C5—P—B | 115.4 (2) | P—C5—C8 | 112.0 (2) |
P—C1—C1i | 115.5 (2) | C6—C5—C7 | 108.3 (3) |
P—C1—C2 | 102.7 (2) | C6—C5—C8 | 109.1 (3) |
C1—C1i—C2 | 113.6 (3) | C7—C5—C8 | 110.1 (3) |
| | | |
P—C1—C1i—Pi | 180.0 | C2—C1—P—C4 | 15.6 (2) |
P—C1—C1i—C2i | 61.7 (3) | C2—C1—P—C5 | 126.2 (2) |
P—C1—C2—C3 | −39.4 (3) | C2—C1—P—B | −100.0 (2) |
P—C4—C3—C2 | −35.6 (3) | C2—C1—C1i—C2i | 180.0 |
C1—P—C4—C3 | 11.3 (2) | C3—C4—P—C5 | −102.2 (2) |
C1—P—C5—C6 | −171.8 (3) | C3—C4—P—B | 131.3 (2) |
C1—P—C5—C7 | 70.7 (3) | C4—P—C5—C6 | −69.3 (3) |
C1—P—C5—C8 | −52.8 (3) | C4—P—C5—C7 | 173.2 (3) |
C1—C1i—Pi—C4i | −139.8 (3) | C4—P—C5—C8 | 49.7 (3) |
C1—C1i—Pi—C5i | 109.7 (3) | C6—C5—P—B | 54.2 (3) |
C1—C1i—Pi—Bi | −24.1 (3) | C7—C5—P—B | −63.3 (3) |
C1—C1i—C2i—C3i | 164.9 (3) | C8—C5—P—B | 173.2 (3) |
C1—C2—C3—C4 | 50.1 (3) | | |
Symmetry code: (i) −x+3/2, −y+1/2, −z+1. |
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