Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101017942/bm1469sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101017942/bm1469Isup2.hkl |
CCDC reference: 183009
The title compound was prepared as described in the Comment and the crude product was purified by flash column chromatography (eluant: hexane/ethyl acetate, 5:1) to yield colourless crystals (m.p. 330.5–332.8 K). 1H NMR (250 MHz, CDCl3): 0.94 (3H, t, J = 7.3 Hz, CH3–CH2), 1.11 (12H, s, CH3), 1.36 (2H, sext, J = 7.3 Hz, CH3–CH2–CH2), 1.75 (2H, pent, J = 7.3 Hz, CH3–CH2–CH2), 2.04 (6H, s, Ar–CH3), 2.28 (3H, s, Ar–CH3), 3.00 (2H, t, J = 7.3 Hz, CH3–CH2–CH2–CH2), 6.84 (2H, br s, Ar–H). 13 C NMR (62.9 MHz, CDCl3): 13.7, 19.9, 21.2, 22.1, 24.5, 26.8, 30.3, 83.0, 127.2, 127.6, 136.8, 137.6, 165.8, 181.6. Analysis calculated for C22H32BNO3: C,71.55, H 8.73, N 3.79%; found: C 71.30, H 8.84, N 3.71%.
Only 28% of the diffraction data have I > 2σ(I). This is due to a general weakness in the data and there is no pattern which would suggest missed lattice centering or a spurious cell doubling or tripling. Methyl H atoms were located from difference Fourier syntheses and were refined as part of a rigid group (C—H fixed at 0.98 Å) which was allowed to rotate but not tip or distort, and with Uiso(H) = 1.5Ueq(C). Other H atoms were placed geometrically (aryl C—H 0.95 Å and methylene C—H 0.99 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C,N).
Data collection: SMART (Bruker, 1997-2001); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C22H32BNO3 | F(000) = 3200 |
Mr = 369.30 | Dx = 1.120 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 33.132 (6) Å | Cell parameters from 52 reflections |
b = 9.9664 (18) Å | θ = 1.5–24.0° |
c = 27.505 (5) Å | µ = 0.07 mm−1 |
β = 105.331 (4)° | T = 150 K |
V = 8759 (3) Å3 | Square prism, colourless |
Z = 16 | 0.23 × 0.12 × 0.08 mm |
Bruker SMART1000 CCD area-detector diffractometer | 7714 independent reflections |
Radiation source: fine-focus sealed tube | 2827 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.123 |
ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −22→39 |
Tmin = 0.577, Tmax = 1.000 | k = −11→11 |
20283 measured reflections | l = −32→29 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 0.85 | w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3 |
7714 reflections | (Δ/σ)max < 0.001 |
505 parameters | Δρmax = 0.67 e Å−3 |
61 restraints | Δρmin = −0.27 e Å−3 |
C22H32BNO3 | V = 8759 (3) Å3 |
Mr = 369.30 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 33.132 (6) Å | µ = 0.07 mm−1 |
b = 9.9664 (18) Å | T = 150 K |
c = 27.505 (5) Å | 0.23 × 0.12 × 0.08 mm |
β = 105.331 (4)° |
Bruker SMART1000 CCD area-detector diffractometer | 7714 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2827 reflections with I > 2σ(I) |
Tmin = 0.577, Tmax = 1.000 | Rint = 0.123 |
20283 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 61 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 0.85 | Δρmax = 0.67 e Å−3 |
7714 reflections | Δρmin = −0.27 e Å−3 |
505 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
B1 | 0.18860 (14) | 0.4803 (5) | 0.67222 (18) | 0.0325 (12) | |
O1 | 0.15931 (8) | 0.1987 (3) | 0.74555 (10) | 0.0431 (8) | |
O2 | 0.19963 (8) | 0.4903 (2) | 0.62788 (9) | 0.0338 (7) | |
O3 | 0.19014 (8) | 0.6005 (2) | 0.69723 (9) | 0.0380 (7) | |
N2 | 0.16948 (10) | 0.1224 (3) | 0.70690 (13) | 0.0422 (9) | |
C1 | 0.19545 (13) | 0.7055 (4) | 0.66187 (15) | 0.0348 (11) | |
C2 | 0.21588 (13) | 0.6264 (4) | 0.62582 (15) | 0.0334 (10) | |
C3 | 0.17970 (12) | 0.2105 (4) | 0.67698 (16) | 0.0348 (11) | |
C4 | 0.17727 (12) | 0.3469 (4) | 0.69395 (15) | 0.0308 (10) | |
C5 | 0.16448 (12) | 0.3315 (4) | 0.73686 (15) | 0.0328 (10) | |
C6 | 0.19009 (13) | 0.1607 (4) | 0.63104 (16) | 0.0318 (10) | |
C7 | 0.15795 (13) | 0.1130 (4) | 0.59088 (16) | 0.0352 (11) | |
C8 | 0.16813 (13) | 0.0652 (4) | 0.54825 (16) | 0.0383 (11) | |
H8A | 0.1464 | 0.0330 | 0.5208 | 0.046* | |
C9 | 0.20874 (14) | 0.0630 (4) | 0.54439 (17) | 0.0397 (12) | |
C10 | 0.24014 (13) | 0.1103 (4) | 0.58483 (17) | 0.0379 (11) | |
H10A | 0.2683 | 0.1091 | 0.5827 | 0.045* | |
C11 | 0.23164 (13) | 0.1589 (4) | 0.62793 (16) | 0.0334 (10) | |
C12 | 0.26644 (12) | 0.2081 (4) | 0.67125 (16) | 0.0451 (12) | |
H12A | 0.2932 | 0.2006 | 0.6625 | 0.068* | |
H12B | 0.2674 | 0.1535 | 0.7012 | 0.068* | |
H12C | 0.2614 | 0.3021 | 0.6783 | 0.068* | |
C13 | 0.11276 (12) | 0.1116 (4) | 0.59272 (16) | 0.0417 (12) | |
H13A | 0.0952 | 0.0747 | 0.5611 | 0.063* | |
H13B | 0.1037 | 0.2034 | 0.5972 | 0.063* | |
H13C | 0.1100 | 0.0559 | 0.6210 | 0.063* | |
C14 | 0.21890 (14) | 0.0124 (4) | 0.49704 (17) | 0.0580 (14) | |
H14A | 0.1931 | −0.0163 | 0.4726 | 0.087* | |
H14B | 0.2382 | −0.0638 | 0.5055 | 0.087* | |
H14C | 0.2320 | 0.0844 | 0.4824 | 0.087* | |
C15 | 0.20384 (13) | 0.6759 (4) | 0.57210 (15) | 0.0483 (13) | |
H15A | 0.2178 | 0.6210 | 0.5518 | 0.072* | |
H15B | 0.2125 | 0.7697 | 0.5712 | 0.072* | |
H15C | 0.1734 | 0.6691 | 0.5584 | 0.072* | |
C16 | 0.26320 (12) | 0.6143 (4) | 0.64494 (17) | 0.0518 (13) | |
H16A | 0.2740 | 0.5634 | 0.6206 | 0.078* | |
H16B | 0.2704 | 0.5676 | 0.6775 | 0.078* | |
H16C | 0.2757 | 0.7041 | 0.6491 | 0.078* | |
C17 | 0.22254 (14) | 0.8163 (4) | 0.69176 (16) | 0.0492 (13) | |
H17A | 0.2074 | 0.8607 | 0.7134 | 0.074* | |
H17B | 0.2291 | 0.8821 | 0.6685 | 0.074* | |
H17C | 0.2486 | 0.7777 | 0.7126 | 0.074* | |
C18 | 0.15211 (13) | 0.7581 (4) | 0.63646 (16) | 0.0460 (12) | |
H18A | 0.1411 | 0.8070 | 0.6611 | 0.069* | |
H18B | 0.1335 | 0.6827 | 0.6229 | 0.069* | |
H18C | 0.1536 | 0.8185 | 0.6089 | 0.069* | |
C19 | 0.15366 (12) | 0.4230 (4) | 0.77390 (15) | 0.0382 (11) | |
H19A | 0.1562 | 0.5169 | 0.7633 | 0.046* | |
H19B | 0.1740 | 0.4099 | 0.8071 | 0.046* | |
C20 | 0.10990 (15) | 0.4010 (5) | 0.77929 (18) | 0.0580 (14) | |
H20A | 0.1062 | 0.4471 | 0.8097 | 0.070* | 0.512 (9) |
H20B | 0.1044 | 0.3040 | 0.7821 | 0.070* | 0.512 (9) |
H20C | 0.1108 | 0.3179 | 0.7993 | 0.070* | 0.488 (9) |
H20D | 0.1037 | 0.4754 | 0.8000 | 0.070* | 0.488 (9) |
C21A | 0.0799 (2) | 0.4610 (14) | 0.7309 (3) | 0.059 (4) | 0.512 (9) |
H21A | 0.0911 | 0.5494 | 0.7244 | 0.070* | 0.512 (9) |
H21B | 0.0806 | 0.4020 | 0.7021 | 0.070* | 0.512 (9) |
C21B | 0.0712 (3) | 0.3846 (9) | 0.7332 (4) | 0.066 (4) | 0.488 (9) |
H21C | 0.0773 | 0.3239 | 0.7076 | 0.079* | 0.488 (9) |
H21D | 0.0467 | 0.3502 | 0.7435 | 0.079* | 0.488 (9) |
C22A | 0.0347 (3) | 0.4796 (12) | 0.7312 (5) | 0.087 (5) | 0.512 (9) |
H22A | 0.0192 | 0.5204 | 0.6994 | 0.130* | 0.512 (9) |
H22B | 0.0333 | 0.5382 | 0.7593 | 0.130* | 0.512 (9) |
H22C | 0.0224 | 0.3922 | 0.7352 | 0.130* | 0.512 (9) |
C22B | 0.0643 (4) | 0.5269 (10) | 0.7140 (5) | 0.060 (4) | 0.488 (9) |
H22D | 0.0404 | 0.5295 | 0.6841 | 0.091* | 0.488 (9) |
H22E | 0.0894 | 0.5590 | 0.7053 | 0.091* | 0.488 (9) |
H22F | 0.0586 | 0.5845 | 0.7403 | 0.091* | 0.488 (9) |
B1A | 0.08846 (15) | 0.0006 (5) | 0.40110 (18) | 0.0344 (12) | |
N2A | 0.11705 (11) | 0.3561 (3) | 0.37449 (13) | 0.0454 (10) | |
O1A | 0.12632 (9) | 0.2805 (3) | 0.33470 (11) | 0.0509 (9) | |
O2A | 0.08039 (8) | −0.0109 (2) | 0.44728 (10) | 0.0375 (7) | |
O3A | 0.08283 (8) | −0.1170 (3) | 0.37447 (10) | 0.0414 (8) | |
C1A | 0.07694 (14) | −0.2228 (4) | 0.40897 (16) | 0.0396 (11) | |
C2A | 0.06054 (13) | −0.1418 (4) | 0.44826 (15) | 0.0370 (11) | |
C3A | 0.10346 (12) | 0.2667 (4) | 0.40129 (16) | 0.0358 (11) | |
C4A | 0.10266 (12) | 0.1326 (4) | 0.38154 (16) | 0.0340 (10) | |
C5A | 0.11766 (13) | 0.1497 (4) | 0.34067 (17) | 0.0420 (12) | |
C6A | 0.09173 (13) | 0.3156 (4) | 0.44646 (15) | 0.0317 (10) | |
C7A | 0.12315 (13) | 0.3626 (4) | 0.48839 (16) | 0.0354 (11) | |
C8A | 0.11199 (13) | 0.4091 (4) | 0.53059 (16) | 0.0365 (11) | |
H8AA | 0.1331 | 0.4416 | 0.5586 | 0.044* | |
C9A | 0.07087 (14) | 0.4093 (4) | 0.53289 (16) | 0.0346 (11) | |
C10A | 0.04017 (13) | 0.3637 (4) | 0.49119 (15) | 0.0352 (11) | |
H10B | 0.0117 | 0.3653 | 0.4922 | 0.042* | |
C11A | 0.04974 (13) | 0.3162 (4) | 0.44841 (16) | 0.0337 (11) | |
C12A | 0.01548 (13) | 0.2680 (4) | 0.40371 (15) | 0.0459 (12) | |
H12D | −0.0117 | 0.2758 | 0.4114 | 0.069* | |
H12E | 0.0205 | 0.1740 | 0.3966 | 0.069* | |
H12F | 0.0154 | 0.3230 | 0.3742 | 0.069* | |
C13A | 0.16866 (12) | 0.3660 (4) | 0.48762 (17) | 0.0463 (12) | |
H13D | 0.1857 | 0.4015 | 0.5197 | 0.069* | |
H13E | 0.1718 | 0.4238 | 0.4600 | 0.069* | |
H13F | 0.1780 | 0.2750 | 0.4826 | 0.069* | |
C14A | 0.05952 (13) | 0.4571 (4) | 0.57979 (15) | 0.0464 (12) | |
H14D | 0.0292 | 0.4512 | 0.5746 | 0.070* | |
H14E | 0.0685 | 0.5505 | 0.5867 | 0.070* | |
H14F | 0.0736 | 0.4007 | 0.6085 | 0.070* | |
C15A | 0.01384 (12) | −0.1174 (4) | 0.43315 (16) | 0.0461 (12) | |
H15D | 0.0053 | −0.0833 | 0.3985 | 0.069* | |
H15E | 0.0067 | −0.0513 | 0.4560 | 0.069* | |
H15F | −0.0008 | −0.2017 | 0.4352 | 0.069* | |
C16A | 0.07476 (14) | −0.1969 (4) | 0.50189 (15) | 0.0519 (13) | |
H16D | 0.0635 | −0.1408 | 0.5244 | 0.078* | |
H16E | 0.1054 | −0.1964 | 0.5132 | 0.078* | |
H16F | 0.0646 | −0.2890 | 0.5025 | 0.078* | |
C17A | 0.11966 (14) | −0.2872 (4) | 0.43053 (18) | 0.0599 (14) | |
H17D | 0.1278 | −0.3370 | 0.4039 | 0.090* | |
H17E | 0.1182 | −0.3489 | 0.4578 | 0.090* | |
H17F | 0.1404 | −0.2172 | 0.4438 | 0.090* | |
C18A | 0.04637 (14) | −0.3259 (4) | 0.37939 (16) | 0.0527 (13) | |
H18D | 0.0190 | −0.2837 | 0.3659 | 0.079* | |
H18E | 0.0437 | −0.4001 | 0.4017 | 0.079* | |
H18F | 0.0567 | −0.3602 | 0.3515 | 0.079* | |
C19A | 0.12705 (15) | 0.0590 (4) | 0.30167 (17) | 0.0518 (13) | |
H19C | 0.1197 | −0.0341 | 0.3084 | 0.062* | |
H19D | 0.1575 | 0.0615 | 0.3048 | 0.062* | |
C20A | 0.10384 (17) | 0.0959 (6) | 0.2484 (2) | 0.0808 (18) | |
H20W | 0.1224 | 0.1648 | 0.2398 | 0.097* | 0.327 (13) |
H20X | 0.1079 | 0.0152 | 0.2292 | 0.097* | 0.327 (13) |
H20Y | 0.1157 | 0.0500 | 0.2234 | 0.097* | 0.673 (13) |
H20Z | 0.1044 | 0.1941 | 0.2430 | 0.097* | 0.673 (13) |
C21 | 0.0612 (5) | 0.1429 (17) | 0.2192 (13) | 0.227 (16)* | 0.327 (13) |
H21E | 0.0639 | 0.2007 | 0.1910 | 0.272* | 0.327 (13) |
H21H | 0.0485 | 0.1971 | 0.2415 | 0.272* | 0.327 (13) |
C21' | 0.0574 (2) | 0.0737 (10) | 0.2370 (4) | 0.086 (4)* | 0.673 (13) |
H21F | 0.0435 | 0.1327 | 0.2085 | 0.103* | 0.673 (13) |
H21G | 0.0480 | 0.1022 | 0.2667 | 0.103* | 0.673 (13) |
C22 | 0.0331 (5) | 0.0256 (19) | 0.1988 (7) | 0.075 (7)* | 0.327 (13) |
H22G | 0.0039 | 0.0554 | 0.1894 | 0.112* | 0.327 (13) |
H22H | 0.0368 | −0.0443 | 0.2247 | 0.112* | 0.327 (13) |
H22I | 0.0403 | −0.0106 | 0.1690 | 0.112* | 0.327 (13) |
C22' | 0.0427 (4) | −0.0677 (10) | 0.2239 (5) | 0.146 (5)* | 0.673 (13) |
H22J | 0.0133 | −0.0757 | 0.2244 | 0.219* | 0.673 (13) |
H22K | 0.0598 | −0.1297 | 0.2486 | 0.219* | 0.673 (13) |
H22L | 0.0454 | −0.0900 | 0.1902 | 0.219* | 0.673 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
B1 | 0.030 (3) | 0.036 (3) | 0.030 (3) | 0.003 (2) | 0.005 (2) | −0.005 (2) |
O1 | 0.059 (2) | 0.0339 (18) | 0.0467 (19) | 0.0006 (15) | 0.0329 (16) | 0.0056 (15) |
O2 | 0.0476 (19) | 0.0243 (15) | 0.0333 (18) | −0.0015 (13) | 0.0172 (14) | −0.0014 (13) |
O3 | 0.059 (2) | 0.0289 (16) | 0.0299 (17) | −0.0009 (14) | 0.0190 (15) | 0.0004 (14) |
N2 | 0.062 (3) | 0.029 (2) | 0.045 (2) | −0.0007 (18) | 0.032 (2) | −0.0014 (18) |
C1 | 0.044 (3) | 0.027 (2) | 0.038 (3) | 0.000 (2) | 0.019 (2) | 0.002 (2) |
C2 | 0.042 (3) | 0.024 (2) | 0.038 (3) | −0.002 (2) | 0.017 (2) | 0.000 (2) |
C3 | 0.036 (3) | 0.030 (2) | 0.042 (3) | 0.003 (2) | 0.016 (2) | 0.004 (2) |
C4 | 0.039 (3) | 0.023 (2) | 0.029 (3) | 0.0026 (19) | 0.008 (2) | 0.0033 (19) |
C5 | 0.043 (3) | 0.021 (2) | 0.034 (3) | 0.0005 (19) | 0.010 (2) | 0.005 (2) |
C6 | 0.041 (3) | 0.021 (2) | 0.035 (3) | 0.003 (2) | 0.013 (2) | 0.003 (2) |
C7 | 0.043 (3) | 0.022 (2) | 0.044 (3) | 0.000 (2) | 0.016 (2) | 0.006 (2) |
C8 | 0.047 (3) | 0.030 (2) | 0.040 (3) | −0.002 (2) | 0.013 (2) | 0.000 (2) |
C9 | 0.050 (3) | 0.034 (3) | 0.043 (3) | 0.001 (2) | 0.026 (3) | −0.001 (2) |
C10 | 0.031 (3) | 0.034 (2) | 0.053 (3) | 0.003 (2) | 0.020 (2) | 0.002 (2) |
C11 | 0.038 (3) | 0.026 (2) | 0.040 (3) | −0.001 (2) | 0.017 (2) | 0.004 (2) |
C12 | 0.043 (3) | 0.043 (3) | 0.054 (3) | 0.003 (2) | 0.020 (3) | 0.002 (2) |
C13 | 0.042 (3) | 0.035 (3) | 0.051 (3) | 0.001 (2) | 0.018 (2) | 0.001 (2) |
C14 | 0.078 (4) | 0.050 (3) | 0.058 (3) | −0.005 (3) | 0.037 (3) | −0.011 (3) |
C15 | 0.077 (4) | 0.033 (3) | 0.041 (3) | −0.001 (2) | 0.027 (3) | 0.004 (2) |
C16 | 0.047 (3) | 0.044 (3) | 0.071 (4) | −0.004 (2) | 0.027 (3) | −0.001 (3) |
C17 | 0.073 (4) | 0.027 (2) | 0.048 (3) | −0.008 (2) | 0.017 (3) | −0.005 (2) |
C18 | 0.050 (3) | 0.039 (3) | 0.054 (3) | 0.009 (2) | 0.023 (2) | 0.007 (2) |
C19 | 0.048 (3) | 0.033 (2) | 0.036 (3) | −0.002 (2) | 0.016 (2) | 0.003 (2) |
C20 | 0.064 (4) | 0.069 (3) | 0.052 (3) | −0.007 (3) | 0.034 (3) | −0.020 (3) |
C21A | 0.033 (7) | 0.082 (12) | 0.053 (9) | −0.012 (8) | −0.003 (7) | −0.030 (9) |
C21B | 0.052 (9) | 0.053 (7) | 0.098 (10) | −0.024 (6) | 0.028 (7) | −0.039 (7) |
C22A | 0.055 (7) | 0.099 (10) | 0.106 (10) | 0.008 (7) | 0.021 (7) | −0.014 (8) |
C22B | 0.045 (10) | 0.089 (9) | 0.044 (8) | 0.002 (7) | 0.005 (7) | 0.003 (6) |
B1A | 0.040 (3) | 0.033 (3) | 0.032 (3) | 0.003 (2) | 0.013 (3) | 0.004 (2) |
N2A | 0.070 (3) | 0.033 (2) | 0.042 (2) | −0.0019 (19) | 0.031 (2) | 0.0016 (18) |
O1A | 0.082 (2) | 0.0329 (18) | 0.053 (2) | −0.0020 (16) | 0.0444 (18) | −0.0003 (15) |
O2A | 0.053 (2) | 0.0279 (16) | 0.0329 (18) | −0.0070 (14) | 0.0141 (15) | 0.0014 (13) |
O3A | 0.059 (2) | 0.0278 (16) | 0.0452 (19) | −0.0050 (14) | 0.0275 (16) | 0.0002 (14) |
C1A | 0.056 (3) | 0.025 (2) | 0.042 (3) | −0.003 (2) | 0.021 (2) | 0.007 (2) |
C2A | 0.052 (3) | 0.025 (2) | 0.037 (3) | −0.007 (2) | 0.017 (2) | 0.004 (2) |
C3A | 0.038 (3) | 0.033 (3) | 0.039 (3) | −0.002 (2) | 0.013 (2) | 0.005 (2) |
C4A | 0.038 (3) | 0.027 (2) | 0.041 (3) | 0.0063 (19) | 0.017 (2) | 0.004 (2) |
C5A | 0.059 (3) | 0.023 (2) | 0.055 (3) | −0.002 (2) | 0.032 (3) | −0.001 (2) |
C6A | 0.045 (3) | 0.021 (2) | 0.032 (3) | −0.001 (2) | 0.016 (2) | 0.0008 (19) |
C7A | 0.042 (3) | 0.026 (2) | 0.040 (3) | −0.001 (2) | 0.014 (2) | 0.004 (2) |
C8A | 0.041 (3) | 0.032 (2) | 0.036 (3) | −0.004 (2) | 0.010 (2) | −0.002 (2) |
C9A | 0.046 (3) | 0.025 (2) | 0.033 (3) | −0.001 (2) | 0.012 (2) | 0.003 (2) |
C10A | 0.037 (3) | 0.030 (2) | 0.042 (3) | 0.001 (2) | 0.016 (2) | 0.003 (2) |
C11A | 0.041 (3) | 0.024 (2) | 0.036 (3) | 0.003 (2) | 0.011 (2) | 0.003 (2) |
C12A | 0.050 (3) | 0.043 (3) | 0.044 (3) | 0.008 (2) | 0.012 (2) | −0.005 (2) |
C13A | 0.041 (3) | 0.039 (3) | 0.063 (3) | 0.000 (2) | 0.021 (2) | 0.008 (2) |
C14A | 0.053 (3) | 0.049 (3) | 0.040 (3) | 0.010 (2) | 0.017 (2) | −0.004 (2) |
C15A | 0.048 (3) | 0.043 (3) | 0.054 (3) | −0.005 (2) | 0.025 (2) | 0.002 (2) |
C16A | 0.079 (4) | 0.037 (3) | 0.042 (3) | −0.006 (2) | 0.020 (3) | 0.012 (2) |
C17A | 0.068 (4) | 0.034 (3) | 0.084 (4) | 0.003 (3) | 0.031 (3) | 0.010 (3) |
C18A | 0.073 (4) | 0.039 (3) | 0.054 (3) | −0.018 (3) | 0.031 (3) | −0.012 (2) |
C19A | 0.073 (4) | 0.035 (3) | 0.061 (4) | 0.000 (2) | 0.041 (3) | 0.000 (2) |
C20A | 0.093 (5) | 0.090 (4) | 0.066 (4) | 0.027 (4) | 0.033 (3) | −0.018 (3) |
B1—O2 | 1.366 (5) | B1A—O2A | 1.370 (5) |
B1—O3 | 1.376 (5) | B1A—C4A | 1.541 (6) |
B1—C4 | 1.544 (6) | N2A—C3A | 1.310 (5) |
O1—C5 | 1.364 (4) | N2A—O1A | 1.427 (4) |
O1—N2 | 1.418 (4) | O1A—C5A | 1.354 (4) |
O2—C2 | 1.465 (4) | O2A—C2A | 1.465 (4) |
O3—C1 | 1.470 (4) | O3A—C1A | 1.466 (4) |
N2—C3 | 1.308 (5) | C1A—C18A | 1.519 (5) |
C1—C18 | 1.515 (5) | C1A—C17A | 1.524 (5) |
C1—C17 | 1.521 (5) | C1A—C2A | 1.558 (5) |
C1—C2 | 1.555 (5) | C2A—C15A | 1.512 (5) |
C2—C15 | 1.508 (5) | C2A—C16A | 1.527 (5) |
C2—C16 | 1.521 (5) | C3A—C4A | 1.441 (5) |
C3—C4 | 1.446 (5) | C3A—C6A | 1.479 (5) |
C3—C6 | 1.481 (5) | C4A—C5A | 1.355 (5) |
C4—C5 | 1.364 (5) | C5A—C19A | 1.497 (5) |
C5—C19 | 1.480 (5) | C6A—C11A | 1.406 (5) |
C6—C7 | 1.399 (5) | C6A—C7A | 1.414 (5) |
C6—C11 | 1.402 (5) | C7A—C8A | 1.388 (5) |
C7—C8 | 1.387 (5) | C7A—C13A | 1.514 (5) |
C7—C13 | 1.512 (5) | C8A—C9A | 1.380 (5) |
C8—C9 | 1.378 (5) | C8A—H8AA | 0.9500 |
C8—H8A | 0.9500 | C9A—C10A | 1.393 (5) |
C9—C10 | 1.389 (5) | C9A—C14A | 1.513 (5) |
C9—C14 | 1.515 (5) | C10A—C11A | 1.381 (5) |
C10—C11 | 1.377 (5) | C10A—H10B | 0.9500 |
C10—H10A | 0.9500 | C11A—C12A | 1.514 (5) |
C11—C12 | 1.504 (5) | C12A—H12D | 0.9800 |
C12—H12A | 0.9800 | C12A—H12E | 0.9800 |
C12—H12B | 0.9800 | C12A—H12F | 0.9800 |
C12—H12C | 0.9800 | C13A—H13D | 0.9800 |
C13—H13A | 0.9800 | C13A—H13E | 0.9800 |
C13—H13B | 0.9800 | C13A—H13F | 0.9800 |
C13—H13C | 0.9800 | C14A—H14D | 0.9800 |
C14—H14A | 0.9800 | C14A—H14E | 0.9800 |
C14—H14B | 0.9800 | C14A—H14F | 0.9800 |
C14—H14C | 0.9800 | C15A—H15D | 0.9800 |
C15—H15A | 0.9800 | C15A—H15E | 0.9800 |
C15—H15B | 0.9800 | C15A—H15F | 0.9800 |
C15—H15C | 0.9800 | C16A—H16D | 0.9800 |
C16—H16A | 0.9800 | C16A—H16E | 0.9800 |
C16—H16B | 0.9800 | C16A—H16F | 0.9800 |
C16—H16C | 0.9800 | C17A—H17D | 0.9800 |
C17—H17A | 0.9800 | C17A—H17E | 0.9800 |
C17—H17B | 0.9800 | C17A—H17F | 0.9800 |
C17—H17C | 0.9800 | C18A—H18D | 0.9800 |
C18—H18A | 0.9800 | C18A—H18E | 0.9800 |
C18—H18B | 0.9800 | C18A—H18F | 0.9800 |
C18—H18C | 0.9800 | C19A—C20A | 1.510 (6) |
C19—C20 | 1.512 (5) | C19A—H19C | 0.9900 |
C19—H19A | 0.9900 | C19A—H19D | 0.9900 |
C19—H19B | 0.9900 | C20A—C21 | 1.503 (8) |
C20—C21B | 1.554 (7) | C20A—C21' | 1.503 (8) |
C20—C21A | 1.556 (7) | C20A—H20W | 0.9900 |
C20—H20A | 0.9900 | C20A—H20X | 0.9900 |
C20—H20B | 0.9900 | C20A—H20Y | 0.9899 |
C20—H20C | 0.9899 | C20A—H20Z | 0.9900 |
C20—H20D | 0.9899 | C21—C22 | 1.508 (2) |
C21A—C22A | 1.511 (2) | C21—H20Z | 1.4963 |
C21A—H21A | 0.9900 | C21—H21E | 0.9900 |
C21A—H21B | 0.9900 | C21—H21H | 0.9900 |
C21B—C22B | 1.510 (2) | C21'—C22' | 1.504 (2) |
C21B—H21C | 0.9900 | C21'—H21F | 0.9900 |
C21B—H21D | 0.9900 | C21'—H21G | 0.9900 |
C22A—H22A | 0.9800 | C22—H22G | 0.9800 |
C22A—H22B | 0.9800 | C22—H22H | 0.9800 |
C22A—H22C | 0.9800 | C22—H22I | 0.9800 |
C22B—H22D | 0.9800 | C22'—H22J | 0.9800 |
C22B—H22E | 0.9800 | C22'—H22K | 0.9800 |
C22B—H22F | 0.9800 | C22'—H22L | 0.9800 |
B1A—O3A | 1.369 (5) | ||
O2—B1—O3 | 113.6 (4) | O2A—B1A—C4A | 123.2 (4) |
O2—B1—C4 | 123.9 (4) | C3A—N2A—O1A | 104.4 (3) |
O3—B1—C4 | 122.5 (4) | C5A—O1A—N2A | 108.6 (3) |
C5—O1—N2 | 108.9 (3) | B1A—O2A—C2A | 106.9 (3) |
B1—O2—C2 | 106.8 (3) | B1A—O3A—C1A | 107.0 (3) |
B1—O3—C1 | 106.5 (3) | O3A—C1A—C18A | 108.9 (3) |
C3—N2—O1 | 105.3 (3) | O3A—C1A—C17A | 106.6 (3) |
O3—C1—C18 | 106.7 (3) | C18A—C1A—C17A | 110.1 (4) |
O3—C1—C17 | 108.4 (3) | O3A—C1A—C2A | 101.9 (3) |
C18—C1—C17 | 110.5 (3) | C18A—C1A—C2A | 114.6 (4) |
O3—C1—C2 | 102.1 (3) | C17A—C1A—C2A | 114.0 (4) |
C18—C1—C2 | 113.6 (3) | O2A—C2A—C15A | 106.5 (3) |
C17—C1—C2 | 114.8 (3) | O2A—C2A—C16A | 108.2 (3) |
O2—C2—C15 | 109.6 (3) | C15A—C2A—C16A | 110.8 (3) |
O2—C2—C16 | 105.6 (3) | O2A—C2A—C1A | 102.0 (3) |
C15—C2—C16 | 110.2 (3) | C15A—C2A—C1A | 114.3 (3) |
O2—C2—C1 | 102.6 (3) | C16A—C2A—C1A | 114.1 (3) |
C15—C2—C1 | 114.3 (3) | N2A—C3A—C4A | 113.2 (4) |
C16—C2—C1 | 113.7 (3) | N2A—C3A—C6A | 117.0 (4) |
N2—C3—C4 | 112.5 (4) | C4A—C3A—C6A | 129.8 (4) |
N2—C3—C6 | 118.0 (3) | C5A—C4A—C3A | 102.8 (4) |
C4—C3—C6 | 129.5 (4) | C5A—C4A—B1A | 127.6 (4) |
C5—C4—C3 | 103.3 (3) | C3A—C4A—B1A | 129.6 (4) |
C5—C4—B1 | 126.5 (4) | O1A—C5A—C4A | 111.0 (4) |
C3—C4—B1 | 130.1 (4) | O1A—C5A—C19A | 113.8 (4) |
C4—C5—O1 | 110.1 (3) | C4A—C5A—C19A | 135.2 (4) |
C4—C5—C19 | 135.5 (4) | C11A—C6A—C7A | 119.3 (4) |
O1—C5—C19 | 114.4 (3) | C11A—C6A—C3A | 121.1 (4) |
C7—C6—C11 | 120.2 (4) | C7A—C6A—C3A | 119.6 (4) |
C7—C6—C3 | 119.2 (4) | C8A—C7A—C6A | 119.4 (4) |
C11—C6—C3 | 120.7 (4) | C8A—C7A—C13A | 119.4 (4) |
C8—C7—C6 | 118.6 (4) | C6A—C7A—C13A | 121.2 (4) |
C8—C7—C13 | 119.3 (4) | C9A—C8A—C7A | 121.5 (4) |
C6—C7—C13 | 122.0 (4) | C9A—C8A—H8AA | 119.2 |
C9—C8—C7 | 122.1 (4) | C7A—C8A—H8AA | 119.2 |
C9—C8—H8A | 118.9 | C8A—C9A—C10A | 118.5 (4) |
C7—C8—H8A | 118.9 | C8A—C9A—C14A | 120.7 (4) |
C8—C9—C10 | 118.2 (4) | C10A—C9A—C14A | 120.9 (4) |
C8—C9—C14 | 121.0 (4) | C11A—C10A—C9A | 122.1 (4) |
C10—C9—C14 | 120.8 (4) | C11A—C10A—H10B | 118.9 |
C11—C10—C9 | 121.9 (4) | C9A—C10A—H10B | 118.9 |
C11—C10—H10A | 119.1 | C10A—C11A—C6A | 119.1 (4) |
C9—C10—H10A | 119.1 | C10A—C11A—C12A | 120.6 (4) |
C10—C11—C6 | 119.0 (4) | C6A—C11A—C12A | 120.3 (4) |
C10—C11—C12 | 120.5 (4) | C11A—C12A—H12D | 109.5 |
C6—C11—C12 | 120.5 (4) | C11A—C12A—H12E | 109.5 |
C11—C12—H12A | 109.5 | H12D—C12A—H12E | 109.5 |
C11—C12—H12B | 109.5 | C11A—C12A—H12F | 109.5 |
H12A—C12—H12B | 109.5 | H12D—C12A—H12F | 109.5 |
C11—C12—H12C | 109.5 | H12E—C12A—H12F | 109.5 |
H12A—C12—H12C | 109.5 | C7A—C13A—H13D | 109.5 |
H12B—C12—H12C | 109.5 | C7A—C13A—H13E | 109.5 |
C7—C13—H13A | 109.5 | H13D—C13A—H13E | 109.5 |
C7—C13—H13B | 109.5 | C7A—C13A—H13F | 109.5 |
H13A—C13—H13B | 109.5 | H13D—C13A—H13F | 109.5 |
C7—C13—H13C | 109.5 | H13E—C13A—H13F | 109.5 |
H13A—C13—H13C | 109.5 | C9A—C14A—H14D | 109.5 |
H13B—C13—H13C | 109.5 | C9A—C14A—H14E | 109.5 |
C9—C14—H14A | 109.5 | H14D—C14A—H14E | 109.5 |
C9—C14—H14B | 109.5 | C9A—C14A—H14F | 109.5 |
H14A—C14—H14B | 109.5 | H14D—C14A—H14F | 109.5 |
C9—C14—H14C | 109.5 | H14E—C14A—H14F | 109.5 |
H14A—C14—H14C | 109.5 | C2A—C15A—H15D | 109.5 |
H14B—C14—H14C | 109.5 | C2A—C15A—H15E | 109.5 |
C2—C15—H15A | 109.5 | H15D—C15A—H15E | 109.5 |
C2—C15—H15B | 109.5 | C2A—C15A—H15F | 109.5 |
H15A—C15—H15B | 109.5 | H15D—C15A—H15F | 109.5 |
C2—C15—H15C | 109.5 | H15E—C15A—H15F | 109.5 |
H15A—C15—H15C | 109.5 | C2A—C16A—H16D | 109.5 |
H15B—C15—H15C | 109.5 | C2A—C16A—H16E | 109.5 |
C2—C16—H16A | 109.5 | H16D—C16A—H16E | 109.5 |
C2—C16—H16B | 109.5 | C2A—C16A—H16F | 109.5 |
H16A—C16—H16B | 109.5 | H16D—C16A—H16F | 109.5 |
C2—C16—H16C | 109.5 | H16E—C16A—H16F | 109.5 |
H16A—C16—H16C | 109.5 | C1A—C17A—H17D | 109.5 |
H16B—C16—H16C | 109.5 | C1A—C17A—H17E | 109.5 |
C1—C17—H17A | 109.5 | H17D—C17A—H17E | 109.5 |
C1—C17—H17B | 109.5 | C1A—C17A—H17F | 109.5 |
H17A—C17—H17B | 109.5 | H17D—C17A—H17F | 109.5 |
C1—C17—H17C | 109.5 | H17E—C17A—H17F | 109.5 |
H17A—C17—H17C | 109.5 | C1A—C18A—H18D | 109.5 |
H17B—C17—H17C | 109.5 | C1A—C18A—H18E | 109.5 |
C1—C18—H18A | 109.5 | H18D—C18A—H18E | 109.5 |
C1—C18—H18B | 109.5 | C1A—C18A—H18F | 109.5 |
H18A—C18—H18B | 109.5 | H18D—C18A—H18F | 109.5 |
C1—C18—H18C | 109.5 | H18E—C18A—H18F | 109.5 |
H18A—C18—H18C | 109.5 | C5A—C19A—C20A | 113.6 (4) |
H18B—C18—H18C | 109.5 | C5A—C19A—H19C | 108.9 |
C5—C19—C20 | 113.0 (3) | C20A—C19A—H19C | 108.9 |
C5—C19—H19A | 109.0 | C5A—C19A—H19D | 108.9 |
C20—C19—H19A | 109.0 | C20A—C19A—H19D | 108.9 |
C5—C19—H19B | 109.0 | H19C—C19A—H19D | 107.7 |
C20—C19—H19B | 109.0 | C21—C20A—C21' | 33.8 (12) |
H19A—C19—H19B | 107.8 | C21—C20A—C19A | 139.4 (16) |
C19—C20—C21B | 122.7 (6) | C21'—C20A—C19A | 113.4 (6) |
C19—C20—C21A | 105.8 (5) | C21—C20A—H20W | 102.2 |
C21B—C20—C21A | 30.7 (5) | C21'—C20A—H20W | 135.9 |
C19—C20—H20A | 110.6 | C19A—C20A—H20W | 102.2 |
C21B—C20—H20A | 118.6 | C21—C20A—H20X | 102.2 |
C21A—C20—H20A | 110.6 | C21'—C20A—H20X | 92.7 |
C19—C20—H20B | 110.6 | C19A—C20A—H20X | 102.2 |
C21B—C20—H20B | 80.2 | H20W—C20A—H20X | 104.8 |
C21A—C20—H20B | 110.6 | C21—C20A—H20Y | 105.3 |
H20A—C20—H20B | 108.7 | C21'—C20A—H20Y | 111.1 |
C19—C20—H20C | 106.7 | C19A—C20A—H20Y | 111.6 |
C21B—C20—H20C | 105.3 | H20W—C20A—H20Y | 76.7 |
C21A—C20—H20C | 135.8 | H20X—C20A—H20Y | 28.3 |
H20A—C20—H20C | 84.9 | C21—C20A—H20Z | 70.4 |
H20B—C20—H20C | 28.4 | C21'—C20A—H20Z | 99.9 |
C19—C20—H20D | 107.4 | C19A—C20A—H20Z | 111.1 |
C21B—C20—H20D | 107.2 | H20W—C20A—H20Z | 40.8 |
C21A—C20—H20D | 91.2 | H20X—C20A—H20Z | 135.5 |
H20A—C20—H20D | 22.3 | H20Y—C20A—H20Z | 109.1 |
H20B—C20—H20D | 128.1 | C20A—C21—C22 | 111.0 (12) |
H20C—C20—H20D | 106.7 | C20A—C21—H20Z | 38.5 |
C22A—C21A—C20 | 116.8 (8) | C22—C21—H20Z | 148.4 |
C22A—C21A—H21A | 108.1 | C20A—C21—H21E | 109.4 |
C20—C21A—H21A | 108.1 | C22—C21—H21E | 109.4 |
C22A—C21A—H21B | 108.1 | H20Z—C21—H21E | 82.6 |
C20—C21A—H21B | 108.1 | C20A—C21—H21H | 109.4 |
H21A—C21A—H21B | 107.3 | C22—C21—H21H | 109.4 |
C22B—C21B—C20 | 101.7 (6) | H20Z—C21—H21H | 93.2 |
C22B—C21B—H21C | 111.4 | H21E—C21—H21H | 108.0 |
C20—C21B—H21C | 111.4 | C20A—C21'—C22' | 115.9 (8) |
C22B—C21B—H21D | 111.4 | C20A—C21'—H21F | 108.3 |
C20—C21B—H21D | 111.4 | C22'—C21'—H21F | 108.3 |
H21C—C21B—H21D | 109.3 | C20A—C21'—H21G | 108.3 |
C21A—C22A—H22A | 109.5 | C22'—C21'—H21G | 108.3 |
C21A—C22A—H22B | 109.5 | H21F—C21'—H21G | 107.4 |
H22A—C22A—H22B | 109.5 | C21—C22—H22G | 109.5 |
C21A—C22A—H22C | 109.5 | C21—C22—H22H | 109.5 |
H22A—C22A—H22C | 109.5 | H22G—C22—H22H | 109.5 |
H22B—C22A—H22C | 109.5 | C21—C22—H22I | 109.5 |
C21B—C22B—H22D | 109.5 | H22G—C22—H22I | 109.5 |
C21B—C22B—H22E | 109.5 | H22H—C22—H22I | 109.5 |
H22D—C22B—H22E | 109.5 | C21'—C22'—H22J | 109.5 |
C21B—C22B—H22F | 109.5 | C21'—C22'—H22K | 109.5 |
H22D—C22B—H22F | 109.5 | H22J—C22'—H22K | 109.5 |
H22E—C22B—H22F | 109.5 | C21'—C22'—H22L | 109.5 |
O3A—B1A—O2A | 113.1 (4) | H22J—C22'—H22L | 109.5 |
O3A—B1A—C4A | 123.7 (4) | H22K—C22'—H22L | 109.5 |
O3—B1—O2—C2 | 8.6 (4) | C3A—N2A—O1A—C5A | −0.2 (4) |
C4—B1—O2—C2 | −168.9 (4) | O3A—B1A—O2A—C2A | −10.6 (5) |
O2—B1—O3—C1 | 11.0 (4) | C4A—B1A—O2A—C2A | 169.7 (4) |
C4—B1—O3—C1 | −171.5 (4) | O2A—B1A—O3A—C1A | −9.8 (5) |
C5—O1—N2—C3 | −0.6 (4) | C4A—B1A—O3A—C1A | 169.9 (4) |
B1—O3—C1—C18 | 95.2 (4) | B1A—O3A—C1A—C18A | 145.8 (4) |
B1—O3—C1—C17 | −145.8 (3) | B1A—O3A—C1A—C17A | −95.5 (4) |
B1—O3—C1—C2 | −24.2 (4) | B1A—O3A—C1A—C2A | 24.3 (4) |
B1—O2—C2—C15 | −144.9 (3) | B1A—O2A—C2A—C15A | −95.4 (4) |
B1—O2—C2—C16 | 96.4 (4) | B1A—O2A—C2A—C16A | 145.4 (4) |
B1—O2—C2—C1 | −23.0 (4) | B1A—O2A—C2A—C1A | 24.8 (4) |
O3—C1—C2—O2 | 28.5 (4) | O3A—C1A—C2A—O2A | −29.5 (4) |
C18—C1—C2—O2 | −86.0 (4) | C18A—C1A—C2A—O2A | −146.9 (3) |
C17—C1—C2—O2 | 145.5 (3) | C17A—C1A—C2A—O2A | 85.0 (4) |
O3—C1—C2—C15 | 147.1 (3) | O3A—C1A—C2A—C15A | 85.0 (4) |
C18—C1—C2—C15 | 32.6 (5) | C18A—C1A—C2A—C15A | −32.4 (5) |
C17—C1—C2—C15 | −95.9 (4) | C17A—C1A—C2A—C15A | −160.5 (3) |
O3—C1—C2—C16 | −85.1 (4) | O3A—C1A—C2A—C16A | −145.9 (3) |
C18—C1—C2—C16 | 160.5 (3) | C18A—C1A—C2A—C16A | 96.6 (4) |
C17—C1—C2—C16 | 32.0 (5) | C17A—C1A—C2A—C16A | −31.5 (5) |
O1—N2—C3—C4 | 0.5 (4) | O1A—N2A—C3A—C4A | −0.4 (5) |
O1—N2—C3—C6 | −177.1 (3) | O1A—N2A—C3A—C6A | 179.2 (3) |
N2—C3—C4—C5 | −0.2 (5) | N2A—C3A—C4A—C5A | 0.8 (5) |
C6—C3—C4—C5 | 177.1 (4) | C6A—C3A—C4A—C5A | −178.7 (4) |
N2—C3—C4—B1 | 176.4 (4) | N2A—C3A—C4A—B1A | −179.1 (4) |
C6—C3—C4—B1 | −6.3 (7) | C6A—C3A—C4A—B1A | 1.4 (7) |
O2—B1—C4—C5 | −177.2 (4) | O3A—B1A—C4A—C5A | −11.0 (7) |
O3—B1—C4—C5 | 5.5 (6) | O2A—B1A—C4A—C5A | 168.6 (4) |
O2—B1—C4—C3 | 6.9 (7) | O3A—B1A—C4A—C3A | 169.0 (4) |
O3—B1—C4—C3 | −170.3 (4) | O2A—B1A—C4A—C3A | −11.4 (7) |
C3—C4—C5—O1 | −0.2 (4) | N2A—O1A—C5A—C4A | 0.8 (5) |
B1—C4—C5—O1 | −177.0 (4) | N2A—O1A—C5A—C19A | −178.7 (3) |
C3—C4—C5—C19 | −177.4 (4) | C3A—C4A—C5A—O1A | −0.9 (5) |
B1—C4—C5—C19 | 5.9 (7) | B1A—C4A—C5A—O1A | 179.0 (4) |
N2—O1—C5—C4 | 0.5 (4) | C3A—C4A—C5A—C19A | 178.4 (5) |
N2—O1—C5—C19 | 178.3 (3) | B1A—C4A—C5A—C19A | −1.7 (8) |
N2—C3—C6—C7 | 72.7 (5) | N2A—C3A—C6A—C11A | 111.1 (4) |
C4—C3—C6—C7 | −104.5 (5) | C4A—C3A—C6A—C11A | −69.4 (6) |
N2—C3—C6—C11 | −106.3 (5) | N2A—C3A—C6A—C7A | −68.8 (5) |
C4—C3—C6—C11 | 76.6 (5) | C4A—C3A—C6A—C7A | 110.7 (5) |
C11—C6—C7—C8 | −0.4 (6) | C11A—C6A—C7A—C8A | −0.3 (6) |
C3—C6—C7—C8 | −179.3 (3) | C3A—C6A—C7A—C8A | 179.6 (4) |
C11—C6—C7—C13 | 179.4 (4) | C11A—C6A—C7A—C13A | −178.9 (4) |
C3—C6—C7—C13 | 0.5 (5) | C3A—C6A—C7A—C13A | 1.0 (5) |
C6—C7—C8—C9 | 0.2 (6) | C6A—C7A—C8A—C9A | 0.7 (6) |
C13—C7—C8—C9 | −179.6 (4) | C13A—C7A—C8A—C9A | 179.4 (4) |
C7—C8—C9—C10 | 0.0 (6) | C7A—C8A—C9A—C10A | −1.2 (6) |
C7—C8—C9—C14 | −179.0 (4) | C7A—C8A—C9A—C14A | 178.4 (4) |
C8—C9—C10—C11 | −0.2 (6) | C8A—C9A—C10A—C11A | 1.4 (6) |
C14—C9—C10—C11 | 178.9 (4) | C14A—C9A—C10A—C11A | −178.3 (4) |
C9—C10—C11—C6 | 0.0 (6) | C9A—C10A—C11A—C6A | −1.0 (6) |
C9—C10—C11—C12 | 179.3 (4) | C9A—C10A—C11A—C12A | −179.7 (4) |
C7—C6—C11—C10 | 0.3 (6) | C7A—C6A—C11A—C10A | 0.4 (6) |
C3—C6—C11—C10 | 179.2 (3) | C3A—C6A—C11A—C10A | −179.5 (3) |
C7—C6—C11—C12 | −179.0 (3) | C7A—C6A—C11A—C12A | 179.2 (3) |
C3—C6—C11—C12 | −0.1 (6) | C3A—C6A—C11A—C12A | −0.7 (6) |
C4—C5—C19—C20 | 122.6 (5) | O1A—C5A—C19A—C20A | −58.1 (5) |
O1—C5—C19—C20 | −54.4 (5) | C4A—C5A—C19A—C20A | 122.7 (6) |
C5—C19—C20—C21B | −45.8 (7) | C5A—C19A—C20A—C21 | −40.5 (13) |
C5—C19—C20—C21A | −74.1 (7) | C5A—C19A—C20A—C21' | −68.0 (6) |
C19—C20—C21A—C22A | −167.2 (9) | C21'—C20A—C21—C22 | −41.0 (11) |
C21B—C20—C21A—C22A | 64.2 (13) | C19A—C20A—C21—C22 | −91 (3) |
C19—C20—C21B—C22B | −74.5 (12) | C21—C20A—C21'—C22' | 131 (3) |
C21A—C20—C21B—C22B | −11.2 (10) | C19A—C20A—C21'—C22' | −81.7 (9) |
Experimental details
Crystal data | |
Chemical formula | C22H32BNO3 |
Mr | 369.30 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 150 |
a, b, c (Å) | 33.132 (6), 9.9664 (18), 27.505 (5) |
β (°) | 105.331 (4) |
V (Å3) | 8759 (3) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.23 × 0.12 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.577, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20283, 7714, 2827 |
Rint | 0.123 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.172, 0.85 |
No. of reflections | 7714 |
No. of parameters | 505 |
No. of restraints | 61 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.27 |
Computer programs: SMART (Bruker, 1997-2001), SMART, SAINT (Bruker, 1999); SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
B1—C4 | 1.544 (6) | N2A—C3A | 1.310 (5) |
O1—C5 | 1.364 (4) | N2A—O1A | 1.427 (4) |
O1—N2 | 1.418 (4) | O1A—C5A | 1.354 (4) |
C3—C4 | 1.446 (5) | C3A—C4A | 1.441 (5) |
C3—C6 | 1.481 (5) | C3A—C6A | 1.479 (5) |
C4—C5 | 1.364 (5) | C4A—C5A | 1.355 (5) |
C5—C19 | 1.480 (5) | C5A—C19A | 1.497 (5) |
B1A—C4A | 1.541 (6) | ||
C5—O1—N2 | 108.9 (3) | C3A—N2A—O1A | 104.4 (3) |
C3—N2—O1 | 105.3 (3) | C5A—O1A—N2A | 108.6 (3) |
N2—C3—C4 | 112.5 (4) | N2A—C3A—C4A | 113.2 (4) |
C5—C4—C3 | 103.3 (3) | C5A—C4A—C3A | 102.8 (4) |
O1—C5—C19 | 114.4 (3) | O1A—C5A—C19A | 113.8 (4) |
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Aromatic and heteroaromatic boronic acids and esters represent one of the most valuable and heavily used classes of synthetic intermediates in organic chemistry. We have recently been investigating new routes for the preparation of aryl boronic esters through cycloaddition reactions of alkynylboronates (Davies et al., 1999; Davies, Johnson & Harrity, 2001). In extending this novel synthetic strategy to heteroaryl boronic esters, we have recently reported a highly regioselective [3 + 2] cycloaddition reaction of nitrile oxides and alkynylboronates (Davies, Wybrow et al., 2001). This route permits the synthesis of a range of densely substituted isoxazole boronic esters in a single step from readily available starting materials and represents an efficient alternative to traditional metallation techniques (Iddon, 1994).
The title compound, (I), was prepared in 73% yield by heating a solution of 2,4,6-trimethylbenzonitrile N-oxide and two equivalents of 2-hex-1-ynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane in ether at reflux for 64 h. The product, (I), was isolated as a single regioisomer and its regiochemical assignment was tentatively made on the basis of the 13C NMR spectrum (C-5 δ 181.6 p.p.m.). In an effort to confirm the assigned regiochemistry and to provide a more routine method for regiochemical identification through correlation with 13C NMR shift, we undertook the X-ray analysis of (I). Accordingly, slow cooling of a solution of (I) in hexanes (341–298 K) provided suitable crystals for X-ray analysis and confirmed the regiochemical assignment as that shown.
The asymmetric unit was found to contain two independent molecules, 1 and 2 (Fig. 1), each containing near coplanar isoxazole and dioxaborolane rings, with torsion angles of 6.2 (6) and 11.3 (7)°, respectively. Additionally, the butyl chain shows a 52–48% occupancy disorder (designated C21A/B and C22A/B) for molecule 1 and 56–44% occupancy disorder (designated C21/21' and C22/22') for molecule 2; anisotropy was not applied to the disordered atoms C21, C21', C22 and C22'. The near coplanarity of these rings suggested conjugation of the oxazole O atom with the boronate moiety, which would, in turn, be reflected in the length of the carbon–boron bond. Surprisingly, however, the C4—B1 bond length of 1.544 (6) Å is only slightly short in comparison to other aryl boronic esters in which the boronate group is almost orthogonal to the aromatic ring and therefore cannot participate in conjugation [for example, hydroquinone boronic esters with a torsion angle of 85° show a C—B bond length of 1.572 (3) Å; Davies et al., 1999]. The orientation of the boronic ester moiety results in the 2,4,6-trimethylphenyl group being twisted out of the plane of the other two rings. The torsion angles in molecules 1 and 2 are 74.6 (5) and 69.1 (6)°, respectively, which are in good agreement with that of related (9-anthryl)-5-methyl-4-isoxazolecarboxylate (80.2°; Mosher et al., 1996). Bond lengths, angles and torsion angles not reported in Table 1 are within expected ranges.