Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023549/hb2397sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023549/hb2397IIIsup2.hkl |
CCDC reference: 651515
To a stirred solution of TBS-protected butenolide, (I) (48.7 mg, 0.12 mmol), in ethyl acetate (0.1 ml) was added 4-nitrophenyl isocyanate (23.9 mg, 0.13 mmol) under nitrogen. The reaction mixture was refluxed for 4 h, cooled to room temperature, stirred for 5 min and filtered. The yellow solid obtained was recrystallized from analytical grade methanol, resulting in colourless blocks of (III) after two weeks at room temperature.
The hydrogen atoms were included in positions calculated each cycle (C—H = 1.00 Å) with Uiso(H) = Ueq(carrier).
We have reported a facile synthesis of alpha-substituted gamma- hydroxybutenolides (Patil & Liu, 2007). In an effort to trap the epimerizable gamma-hydroxy group of butenolide, (I), using an isocyanate, (II), we report the synthesis and structure of the title compound, (III). This molecule contains a substituted dihydro-1H-furo[3,2-d]oxazole-2,5-dione ring, which is a new bicyclic oxazole-dione ring.
For background literature, see Patil & Liu (2007).
Data collection: CAD-4 Software (Schagen et al., 1989); cell refinement: CAD-4 Software; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 1996); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: local programs.
C28H32N2O9Si | Z = 2 |
Mr = 568.7 | F(000) = 600.0 |
Triclinic, P1 | Dx = 1.28 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.680 (3) Å | Cell parameters from 11 reflections |
b = 11.674 (5) Å | θ = 10–11° |
c = 13.565 (6) Å | µ = 0.13 mm−1 |
α = 88.75 (3)° | T = 294 K |
β = 79.74 (2)° | Block, colourless |
γ = 77.13 (3)° | 0.25 × 0.20 × 0.18 mm |
V = 1470.2 (9) Å3 |
Enraf–Nonius CAD-4 diffractometer | θmax = 25° |
ω–2θ scans | h = −11→11 |
5435 measured reflections | k = 0→13 |
5155 independent reflections | l = −16→16 |
3251 reflections with I > 2σ(I) | 1 standard reflections every 30 min |
Rint = 0.014 | intensity decay: none |
Refinement on F | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(F) + 0.0004F2] |
wR(F2) = 0.056 | (Δ/σ)max = 0.004 |
S = 1.63 | Δρmax = 0.35 e Å−3 |
3251 reflections | Δρmin = −0.31 e Å−3 |
349 parameters |
C28H32N2O9Si | γ = 77.13 (3)° |
Mr = 568.7 | V = 1470.2 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.680 (3) Å | Mo Kα radiation |
b = 11.674 (5) Å | µ = 0.13 mm−1 |
c = 13.565 (6) Å | T = 294 K |
α = 88.75 (3)° | 0.25 × 0.20 × 0.18 mm |
β = 79.74 (2)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.014 |
5435 measured reflections | 1 standard reflections every 30 min |
5155 independent reflections | intensity decay: none |
3251 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.049 | 349 parameters |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.63 | Δρmax = 0.35 e Å−3 |
3251 reflections | Δρmin = −0.31 e Å−3 |
x | y | z | Uiso*/Ueq | ||
Si | −0.08195 (9) | 0.80484 (8) | 0.28619 (7) | 0.0587 (2) | |
O1 | 0.0289 (3) | 0.6174 (2) | 0.6306 (2) | 0.0848 (6) | |
O2 | 0.1842 (2) | 0.7201 (2) | 0.5547 (2) | 0.0633 (5) | |
O3 | 0.4176 (2) | 0.6957 (2) | 0.4719 (2) | 0.0610 (5) | |
O4 | 0.6132 (2) | 0.5552 (2) | 0.4210 (2) | 0.0676 (5) | |
O5 | 0.4899 (4) | 0.0689 (3) | 0.1494 (3) | 0.1317 (9) | |
O6 | 0.6812 (4) | 0.1245 (3) | 0.0786 (3) | 0.175 (1) | |
O7 | 0.3549 (2) | 0.5878 (2) | 0.1139 (2) | 0.0739 (5) | |
O8 | 0.5189 (2) | 0.6936 (2) | 0.1211 (1) | 0.0619 (5) | |
O9 | 0.0631 (2) | 0.7679 (2) | 0.3410 (1) | 0.0492 (4) | |
N1 | 0.3987 (2) | 0.5594 (2) | 0.3654 (2) | 0.0450 (5) | |
N2 | 0.5680 (5) | 0.1378 (3) | 0.1371 (3) | 0.1077 (9) | |
C1 | 0.2516 (3) | 0.6296 (2) | 0.3915 (2) | 0.0407 (5) | |
C2 | 0.1478 (3) | 0.5681 (3) | 0.4599 (2) | 0.0456 (6) | |
C3 | 0.1107 (3) | 0.6329 (3) | 0.5571 (2) | 0.0568 (7) | |
C4 | 0.2720 (3) | 0.7247 (3) | 0.4602 (2) | 0.0518 (6) | |
C5 | 0.4890 (3) | 0.5969 (3) | 0.4187 (2) | 0.0531 (6) | |
C6 | 0.4399 (3) | 0.4533 (2) | 0.3081 (2) | 0.0459 (6) | |
C7 | 0.5839 (3) | 0.4126 (3) | 0.2643 (3) | 0.0688 (8) | |
C8 | 0.6237 (4) | 0.3104 (3) | 0.2080 (3) | 0.0861 (9) | |
C9 | 0.5229 (4) | 0.2480 (3) | 0.1969 (3) | 0.0721 (8) | |
C10 | 0.3809 (4) | 0.2869 (3) | 0.2384 (2) | 0.0617 (7) | |
C11 | 0.3395 (3) | 0.3907 (3) | 0.2929 (2) | 0.0522 (6) | |
C12 | 0.1906 (3) | 0.6864 (2) | 0.2996 (2) | 0.0445 (6) | |
C13 | 0.2981 (3) | 0.7435 (3) | 0.2322 (2) | 0.0464 (6) | |
C14 | 0.3029 (3) | 0.8543 (3) | 0.2396 (2) | 0.0651 (7) | |
C15 | 0.3908 (3) | 0.6662 (3) | 0.1503 (2) | 0.0511 (6) | |
C16 | 0.6105 (4) | 0.6225 (3) | 0.0376 (3) | 0.0742 (8) | |
C17 | 0.7291 (3) | 0.6814 (3) | −0.0059 (2) | 0.0540 (7) | |
C18 | 0.7153 (3) | 0.8004 (3) | −0.0022 (2) | 0.0613 (7) | |
C19 | 0.8243 (4) | 0.8509 (3) | −0.0514 (3) | 0.0816 (9) | |
C20 | 0.9458 (4) | 0.7817 (4) | −0.1050 (3) | 0.103 (1) | |
C21 | 0.9597 (4) | 0.6624 (4) | −0.1092 (3) | 0.099 (1) | |
C22 | 0.8527 (4) | 0.6119 (3) | −0.0592 (3) | 0.0712 (8) | |
C23 | −0.1238 (4) | 0.6702 (3) | 0.2413 (3) | 0.0854 (9) | |
C24 | −0.0455 (5) | 0.9020 (4) | 0.1812 (4) | 0.121 (1) | |
C25 | −0.2271 (4) | 0.8814 (3) | 0.3883 (3) | 0.079 (1) | |
C26 | −0.2458 (4) | 0.8042 (4) | 0.4791 (3) | 0.108 (2) | |
C27 | −0.1963 (6) | 0.9921 (5) | 0.4198 (5) | 0.170 (2) | |
C28 | −0.3707 (4) | 0.9073 (4) | 0.3484 (4) | 0.126 (2) | |
H1C2 | 0.1954 | 0.4843 | 0.4690 | 0.046* | |
H2C2 | 0.0592 | 0.5714 | 0.4307 | 0.046* | |
HC4 | 0.2476 | 0.8042 | 0.4306 | 0.052* | |
HC7 | 0.6575 | 0.4574 | 0.2738 | 0.069* | |
HC8 | 0.7263 | 0.2814 | 0.1751 | 0.086* | |
HC10 | 0.3085 | 0.2406 | 0.2294 | 0.062* | |
HC11 | 0.2355 | 0.4214 | 0.3218 | 0.052* | |
HC12 | 0.1656 | 0.6248 | 0.2604 | 0.045* | |
H1C14 | 0.2330 | 0.9066 | 0.2920 | 0.065* | |
H2C14 | 0.3765 | 0.8865 | 0.1927 | 0.065* | |
H1C16 | 0.5524 | 0.6140 | −0.0147 | 0.074* | |
H2C16 | 0.6524 | 0.5430 | 0.0619 | 0.074* | |
HC18 | 0.6258 | 0.8514 | 0.0363 | 0.061* | |
HC19 | 0.8141 | 0.9379 | −0.0476 | 0.082* | |
HC20 | 1.0244 | 0.8179 | −0.1412 | 0.103* | |
HC21 | 1.0484 | 0.6118 | −0.1489 | 0.099* | |
HC22 | 0.8645 | 0.5246 | −0.0614 | 0.071* | |
H1C23 | −0.2104 | 0.6920 | 0.2084 | 0.085* | |
H2C23 | −0.0398 | 0.6274 | 0.1918 | 0.085* | |
H3C23 | −0.1436 | 0.6183 | 0.2993 | 0.085* | |
H1C24 | −0.1320 | 0.9243 | 0.1482 | 0.121* | |
H2C24 | −0.0235 | 0.9745 | 0.2068 | 0.121* | |
H3C24 | 0.0388 | 0.8602 | 0.1315 | 0.121* | |
H1C26 | −0.3241 | 0.8478 | 0.5321 | 0.132* | |
H2C26 | −0.2721 | 0.7309 | 0.4593 | 0.126* | |
H3C26 | −0.1537 | 0.7831 | 0.5057 | 0.158* | |
H1C27 | −0.2755 | 1.0311 | 0.4743 | 0.220* | |
H2C27 | −0.1030 | 0.9746 | 0.4450 | 0.209* | |
H3C27 | −0.1896 | 1.0455 | 0.3613 | 0.219* | |
H1C28 | −0.4501 | 0.9484 | 0.4019 | 0.158* | |
H2C28 | −0.3628 | 0.9585 | 0.2885 | 0.183* | |
H3C28 | −0.3920 | 0.8318 | 0.3290 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si | 0.0498 (5) | 0.0596 (5) | 0.0659 (5) | −0.0102 (4) | −0.0114 (4) | 0.0070 (4) |
O1 | 0.083 (1) | 0.118 (2) | 0.055 (1) | −0.046 (1) | 0.017 (1) | −0.011 (1) |
O2 | 0.065 (1) | 0.078 (1) | 0.049 (1) | −0.027 (1) | −0.0001 (9) | −0.0165 (9) |
O3 | 0.055 (1) | 0.071 (1) | 0.064 (1) | −0.0302 (9) | −0.0105 (9) | −0.012 (1) |
O4 | 0.041 (1) | 0.087 (1) | 0.081 (1) | −0.025 (1) | −0.0166 (9) | 0.003 (1) |
O5 | 0.176 (2) | 0.064 (2) | 0.161 (2) | −0.003 (2) | −0.072 (2) | −0.020 (2) |
O6 | 0.132 (3) | 0.144 (3) | 0.215 (3) | 0.026 (2) | 0.001 (2) | −0.104 (2) |
O7 | 0.082 (1) | 0.078 (1) | 0.064 (1) | −0.039 (1) | 0.012 (1) | −0.023 (1) |
O8 | 0.057 (1) | 0.074 (1) | 0.052 (1) | −0.0241 (9) | 0.0128 (9) | −0.0151 (9) |
O9 | 0.0393 (9) | 0.053 (1) | 0.052 (1) | −0.0062 (8) | −0.0028 (8) | −0.0068 (8) |
N1 | 0.034 (1) | 0.051 (1) | 0.052 (1) | −0.0138 (9) | −0.0080 (9) | −0.002 (1) |
N2 | 0.112 (2) | 0.069 (2) | 0.128 (3) | 0.025 (2) | −0.041 (2) | −0.028 (2) |
C1 | 0.034 (1) | 0.046 (1) | 0.043 (1) | −0.012 (1) | −0.003 (1) | −0.003 (1) |
C2 | 0.041 (1) | 0.054 (2) | 0.042 (1) | −0.016 (1) | −0.002 (1) | −0.002 (1) |
C3 | 0.051 (2) | 0.068 (2) | 0.054 (2) | −0.021 (1) | −0.005 (1) | −0.003 (1) |
C4 | 0.049 (2) | 0.063 (2) | 0.047 (2) | −0.021 (1) | −0.004 (1) | −0.006 (1) |
C5 | 0.048 (2) | 0.063 (2) | 0.053 (2) | −0.026 (1) | −0.006 (1) | 0.004 (1) |
C6 | 0.044 (1) | 0.045 (2) | 0.048 (2) | −0.009 (1) | −0.008 (1) | 0.005 (1) |
C7 | 0.043 (2) | 0.072 (2) | 0.086 (2) | −0.005 (1) | −0.007 (2) | −0.011 (2) |
C8 | 0.056 (2) | 0.079 (2) | 0.111 (3) | 0.016 (2) | −0.014 (2) | −0.030 (2) |
C9 | 0.083 (2) | 0.049 (2) | 0.077 (2) | 0.012 (2) | −0.027 (2) | −0.013 (2) |
C10 | 0.075 (2) | 0.050 (2) | 0.063 (2) | −0.015 (1) | −0.016 (2) | 0.001 (1) |
C11 | 0.054 (2) | 0.050 (2) | 0.052 (2) | −0.015 (1) | −0.005 (1) | −0.002 (1) |
C12 | 0.040 (1) | 0.046 (2) | 0.046 (1) | −0.013 (1) | −0.001 (1) | −0.005 (1) |
C13 | 0.049 (2) | 0.046 (2) | 0.044 (2) | −0.015 (1) | −0.002 (1) | −0.001 (1) |
C14 | 0.068 (2) | 0.056 (2) | 0.068 (2) | −0.023 (1) | 0.008 (1) | −0.005 (1) |
C15 | 0.058 (2) | 0.055 (2) | 0.039 (1) | −0.017 (1) | −0.001 (1) | 0.002 (1) |
C16 | 0.077 (2) | 0.076 (2) | 0.059 (2) | −0.024 (2) | 0.024 (1) | −0.018 (2) |
C17 | 0.054 (2) | 0.067 (2) | 0.039 (1) | −0.016 (1) | 0.003 (1) | −0.005 (1) |
C18 | 0.059 (2) | 0.061 (2) | 0.057 (2) | −0.013 (1) | 0.007 (1) | −0.006 (1) |
C19 | 0.077 (2) | 0.072 (2) | 0.092 (2) | −0.023 (2) | 0.005 (2) | −0.001 (2) |
C20 | 0.074 (2) | 0.091 (3) | 0.128 (3) | −0.030 (2) | 0.035 (2) | −0.006 (2) |
C21 | 0.062 (2) | 0.090 (3) | 0.125 (3) | −0.011 (2) | 0.031 (2) | −0.016 (2) |
C22 | 0.060 (2) | 0.071 (2) | 0.073 (2) | −0.012 (2) | 0.011 (2) | −0.008 (2) |
C23 | 0.077 (2) | 0.090 (2) | 0.096 (2) | −0.014 (2) | −0.034 (2) | −0.018 (2) |
C24 | 0.098 (3) | 0.150 (3) | 0.123 (3) | −0.037 (3) | −0.040 (2) | 0.070 (2) |
C25 | 0.058 (1) | 0.059 (2) | 0.113 (2) | −0.003 (1) | −0.008 (1) | −0.013 (1) |
C26 | 0.069 (2) | 0.140 (3) | 0.102 (2) | −0.007 (3) | −0.008 (2) | 0.011 (2) |
C27 | 0.158 (4) | 0.107 (3) | 0.226 (4) | −0.057 (3) | 0.065 (4) | −0.097 (3) |
C28 | 0.051 (2) | 0.159 (4) | 0.139 (3) | 0.031 (2) | −0.010 (1) | 0.019 (3) |
Si—O9 | 1.673 (2) | C12—HC12 | 1.000 |
Si—C23 | 1.849 (4) | C13—C14 | 1.312 (4) |
Si—C24 | 1.835 (4) | C13—C15 | 1.477 (4) |
Si—C25 | 1.869 (4) | C14—H1C14 | 1.000 |
O1—C3 | 1.195 (3) | C14—H2C14 | 1.000 |
O2—C3 | 1.363 (3) | C16—C17 | 1.494 (4) |
O2—C4 | 1.413 (3) | C16—H1C16 | 1.000 |
O3—C4 | 1.411 (3) | C16—H2C16 | 1.000 |
O3—C5 | 1.353 (4) | C17—C18 | 1.367 (4) |
O4—C5 | 1.198 (3) | C17—C22 | 1.378 (4) |
O5—N2 | 1.211 (4) | C18—C19 | 1.384 (4) |
O6—N2 | 1.214 (5) | C18—HC18 | 1.000 |
O7—C15 | 1.195 (3) | C19—C20 | 1.365 (5) |
O8—C15 | 1.339 (3) | C19—HC19 | 1.000 |
O8—C16 | 1.454 (3) | C20—C21 | 1.370 (5) |
O9—C12 | 1.413 (3) | C20—HC20 | 1.000 |
N1—C1 | 1.462 (3) | C21—C22 | 1.373 (5) |
N1—C5 | 1.374 (3) | C21—HC21 | 1.000 |
N1—C6 | 1.417 (3) | C22—HC22 | 1.000 |
N2—C9 | 1.474 (4) | C23—H1C23 | 1.000 |
C1—C2 | 1.532 (4) | C23—H2C23 | 1.000 |
C1—C4 | 1.533 (4) | C23—H3C23 | 1.000 |
C1—C12 | 1.547 (4) | C24—H1C24 | 1.000 |
C2—C3 | 1.480 (4) | C24—H2C24 | 1.000 |
C2—H1C2 | 1.000 | C24—H3C24 | 1.000 |
C2—H2C2 | 1.000 | C25—C26 | 1.519 (5) |
C4—HC4 | 1.000 | C25—C27 | 1.477 (5) |
C6—C7 | 1.394 (4) | C25—C28 | 1.546 (5) |
C6—C11 | 1.385 (4) | C26—H1C26 | 1.000 |
C7—C8 | 1.373 (5) | C26—H2C26 | 1.000 |
C7—HC7 | 1.000 | C26—H3C26 | 1.000 |
C8—C9 | 1.370 (5) | C27—H1C27 | 1.000 |
C8—HC8 | 1.000 | C27—H2C27 | 1.000 |
C9—C10 | 1.367 (5) | C27—H3C27 | 1.000 |
C10—C11 | 1.376 (4) | C28—H1C28 | 1.000 |
C10—HC10 | 1.000 | C28—H2C28 | 1.000 |
C11—HC11 | 1.000 | C28—H3C28 | 1.000 |
C12—C13 | 1.518 (4) | ||
O9—Si—C23 | 109.3 (1) | C13—C14—H1C14 | 120.0 |
O9—Si—C24 | 109.2 (2) | C13—C14—H2C14 | 120.0 |
O9—Si—C25 | 103.9 (1) | H1C14—C14—H2C14 | 120.0 |
C23—Si—C24 | 110.5 (2) | O7—C15—O8 | 123.6 (3) |
C23—Si—C25 | 111.7 (2) | O7—C15—C13 | 123.4 (3) |
C24—Si—C25 | 112.1 (2) | O8—C15—C13 | 113.0 (3) |
C3—O2—C4 | 111.5 (2) | O8—C16—C17 | 109.0 (3) |
C4—O3—C5 | 110.7 (2) | O8—C16—H1C16 | 109.6 |
C15—O8—C16 | 114.4 (2) | O8—C16—H2C16 | 109.6 |
Si—O9—C12 | 124.0 (2) | C17—C16—H1C16 | 109.6 |
C1—N1—C5 | 111.1 (2) | C17—C16—H2C16 | 109.6 |
C1—N1—C6 | 125.2 (2) | H1C16—C16—H2C16 | 109.5 |
C5—N1—C6 | 122.8 (2) | C16—C17—C18 | 123.1 (3) |
O5—N2—O6 | 125.5 (4) | C16—C17—C22 | 117.3 (3) |
O5—N2—C9 | 118.0 (4) | C18—C17—C22 | 119.4 (3) |
O6—N2—C9 | 116.5 (4) | C17—C18—C19 | 120.4 (3) |
N1—C1—C2 | 114.5 (2) | C17—C18—HC18 | 119.8 |
N1—C1—C4 | 101.4 (2) | C19—C18—HC18 | 119.8 |
N1—C1—C12 | 113.1 (2) | C18—C19—C20 | 119.9 (4) |
C2—C1—C4 | 103.2 (2) | C18—C19—HC19 | 120.1 |
C2—C1—C12 | 113.2 (2) | C20—C19—HC19 | 120.1 |
C4—C1—C12 | 110.2 (2) | C19—C20—C21 | 119.8 (3) |
C1—C2—C3 | 106.2 (2) | C19—C20—HC20 | 120.1 |
C1—C2—H1C2 | 110.3 | C21—C20—HC20 | 120.1 |
C1—C2—H2C2 | 110.3 | C20—C21—C22 | 120.5 (3) |
C3—C2—H1C2 | 110.3 | C20—C21—HC21 | 119.8 |
C3—C2—H2C2 | 110.3 | C22—C21—HC21 | 119.8 |
H1C2—C2—H2C2 | 109.5 | C17—C22—C21 | 120.0 (3) |
O1—C3—O2 | 120.8 (3) | C17—C22—HC22 | 120.0 |
O1—C3—C2 | 128.7 (3) | C21—C22—HC22 | 120.0 |
O2—C3—C2 | 110.5 (2) | Si—C23—H1C23 | 109.5 |
O2—C4—O3 | 108.8 (2) | Si—C23—H2C23 | 109.5 |
O2—C4—C1 | 108.6 (2) | Si—C23—H3C23 | 109.5 |
O2—C4—HC4 | 110.9 | H1C23—C23—H2C23 | 109.5 |
O3—C4—C1 | 106.7 (2) | H1C23—C23—H3C23 | 109.5 |
O3—C4—HC4 | 110.9 | H2C23—C23—H3C23 | 109.5 |
C1—C4—HC4 | 110.9 | Si—C24—H1C24 | 109.5 |
O3—C5—O4 | 121.3 (3) | Si—C24—H2C24 | 109.5 |
O3—C5—N1 | 109.7 (3) | Si—C24—H3C24 | 109.5 |
O4—C5—N1 | 128.9 (3) | H1C24—C24—H2C24 | 109.5 |
N1—C6—C7 | 119.4 (3) | H1C24—C24—H3C24 | 109.5 |
N1—C6—C11 | 121.3 (3) | H2C24—C24—H3C24 | 109.5 |
C7—C6—C11 | 119.3 (3) | Si—C25—C26 | 111.6 (3) |
C6—C7—C8 | 119.4 (3) | Si—C25—C27 | 111.2 (3) |
C6—C7—HC7 | 120.3 | Si—C25—C28 | 108.0 (3) |
C8—C7—HC7 | 120.3 | C26—C25—C27 | 108.9 (4) |
C7—C8—C9 | 120.1 (3) | C26—C25—C28 | 107.0 (3) |
C7—C8—HC8 | 120.0 | C27—C25—C28 | 110.0 (4) |
C9—C8—HC8 | 120.0 | C25—C26—H1C26 | 109.5 |
N2—C9—C8 | 119.3 (4) | C25—C26—H2C26 | 109.5 |
N2—C9—C10 | 119.2 (4) | C25—C26—H3C26 | 109.5 |
C8—C9—C10 | 121.5 (3) | H1C26—C26—H2C26 | 109.5 |
C9—C10—C11 | 118.8 (3) | H1C26—C26—H3C26 | 109.5 |
C9—C10—HC10 | 120.6 | H2C26—C26—H3C26 | 109.5 |
C11—C10—HC10 | 120.6 | C25—C27—H1C27 | 109.5 |
C6—C11—C10 | 120.8 (3) | C25—C27—H2C27 | 109.5 |
C6—C11—HC11 | 119.6 | C25—C27—H3C27 | 109.5 |
C10—C11—HC11 | 119.6 | H1C27—C27—H2C27 | 109.5 |
O9—C12—C1 | 104.6 (2) | H1C27—C27—H3C27 | 109.5 |
O9—C12—C13 | 112.8 (2) | H2C27—C27—H3C27 | 109.5 |
O9—C12—HC12 | 109.2 | C25—C28—H1C28 | 109.5 |
C1—C12—C13 | 111.7 (2) | C25—C28—H2C28 | 109.5 |
C1—C12—HC12 | 109.2 | C25—C28—H3C28 | 109.5 |
C13—C12—HC12 | 109.2 | H1C28—C28—H2C28 | 109.5 |
C12—C13—C14 | 124.0 (3) | H1C28—C28—H3C28 | 109.5 |
C12—C13—C15 | 114.3 (2) | H2C28—C28—H3C28 | 109.5 |
C14—C13—C15 | 121.5 (3) | ||
C23—Si—O9—C12 | 46.3 (2) | H2C2—C2—C3—O1 | 57.5 |
C24—Si—O9—C12 | −74.7 (3) | H2C2—C2—C3—O2 | −122.0 |
C25—Si—O9—C12 | 165.6 (2) | N1—C6—C7—C8 | −179.4 (3) |
O9—Si—C23—H1C23 | 180.0 | N1—C6—C7—HC7 | 0.6 |
O9—Si—C23—H2C23 | −60.0 | C11—C6—C7—C8 | −0.9 (5) |
O9—Si—C23—H3C23 | 60.0 | C11—C6—C7—HC7 | 179.1 |
C24—Si—C23—H1C23 | −59.8 | N1—C6—C11—C10 | −179.0 (3) |
C24—Si—C23—H2C23 | 60.2 | N1—C6—C11—HC11 | 1.0 |
C24—Si—C23—H3C23 | −179.8 | C7—C6—C11—C10 | 2.5 (4) |
C25—Si—C23—H1C23 | 65.6 | C7—C6—C11—HC11 | −177.5 |
C25—Si—C23—H2C23 | −174.4 | C6—C7—C8—C9 | −1.3 (6) |
C25—Si—C23—H3C23 | −54.4 | C6—C7—C8—HC8 | 178.7 |
O9—Si—C24—H1C24 | −180.0 | HC7—C7—C8—C9 | 178.7 |
O9—Si—C24—H2C24 | −60.0 | HC7—C7—C8—HC8 | −1.3 |
O9—Si—C24—H3C24 | 60.0 | C7—C8—C9—N2 | −179.3 (3) |
C23—Si—C24—H1C24 | 59.8 | C7—C8—C9—C10 | 2.0 (6) |
C23—Si—C24—H2C24 | 179.8 | HC8—C8—C9—N2 | 0.7 |
C23—Si—C24—H3C24 | −60.2 | HC8—C8—C9—C10 | −178.0 |
C25—Si—C24—H1C24 | −65.4 | N2—C9—C10—C11 | −179.0 (3) |
C25—Si—C24—H2C24 | 54.6 | N2—C9—C10—HC10 | 1.0 |
C25—Si—C24—H3C24 | 174.6 | C8—C9—C10—C11 | −0.4 (5) |
O9—Si—C25—C26 | −56.4 (3) | C8—C9—C10—HC10 | 179.6 |
O9—Si—C25—C27 | 65.4 (4) | C9—C10—C11—C6 | −1.9 (5) |
O9—Si—C25—C28 | −173.8 (3) | C9—C10—C11—HC11 | 178.1 |
C23—Si—C25—C26 | 61.3 (3) | HC10—C10—C11—C6 | 178.1 |
C23—Si—C25—C27 | −176.9 (4) | HC10—C10—C11—HC11 | −1.9 |
C23—Si—C25—C28 | −56.1 (3) | O9—C12—C13—C14 | 24.8 (4) |
C24—Si—C25—C26 | −174.2 (3) | O9—C12—C13—C15 | −150.0 (2) |
C24—Si—C25—C27 | −52.4 (4) | C1—C12—C13—C14 | −92.6 (4) |
C24—Si—C25—C28 | 68.4 (3) | C1—C12—C13—C15 | 92.5 (3) |
C4—O2—C3—O1 | −178.6 (3) | HC12—C12—C13—C14 | 146.5 |
C4—O2—C3—C2 | 1.0 (3) | HC12—C12—C13—C15 | −28.4 |
C3—O2—C4—O3 | −114.7 (3) | C12—C13—C14—H1C14 | 0.0 |
C3—O2—C4—C1 | 1.0 (3) | C12—C13—C14—H2C14 | −180.0 |
C3—O2—C4—HC4 | 123.1 | C15—C13—C14—H1C14 | 174.5 |
C5—O3—C4—O2 | 117.7 (2) | C15—C13—C14—H2C14 | −5.5 |
C5—O3—C4—C1 | 0.8 (3) | C12—C13—C15—O7 | 28.0 (4) |
C5—O3—C4—HC4 | −120.0 | C12—C13—C15—O8 | −152.2 (2) |
C4—O3—C5—O4 | −177.6 (3) | C14—C13—C15—O7 | −147.0 (3) |
C4—O3—C5—N1 | 3.2 (3) | C14—C13—C15—O8 | 32.8 (4) |
C16—O8—C15—O7 | 2.3 (4) | O8—C16—C17—C18 | −28.4 (4) |
C16—O8—C15—C13 | −177.5 (2) | O8—C16—C17—C22 | 157.1 (3) |
C15—O8—C16—C17 | 164.3 (3) | H1C16—C16—C17—C18 | 91.5 |
C15—O8—C16—H1C16 | 44.3 | H1C16—C16—C17—C22 | −83.0 |
C15—O8—C16—H2C16 | −75.8 | H2C16—C16—C17—C18 | −148.4 |
Si—O9—C12—C1 | −149.1 (2) | H2C16—C16—C17—C22 | 37.2 |
Si—O9—C12—C13 | 89.4 (2) | C16—C17—C18—C19 | −174.3 (3) |
Si—O9—C12—HC12 | −32.3 | C16—C17—C18—HC18 | 5.7 |
C5—N1—C1—C2 | −104.1 (3) | C22—C17—C18—C19 | 0.0 (5) |
C5—N1—C1—C4 | 6.2 (3) | C22—C17—C18—HC18 | 180.0 |
C5—N1—C1—C12 | 124.2 (2) | C16—C17—C22—C21 | 173.6 (4) |
C6—N1—C1—C2 | 64.8 (3) | C16—C17—C22—HC22 | −6.4 |
C6—N1—C1—C4 | 175.1 (2) | C18—C17—C22—C21 | −1.0 (5) |
C6—N1—C1—C12 | −67.0 (3) | C18—C17—C22—HC22 | 179.0 |
C1—N1—C5—O3 | −6.2 (3) | C17—C18—C19—C20 | 0.8 (6) |
C1—N1—C5—O4 | 174.7 (3) | C17—C18—C19—HC19 | −179.2 |
C6—N1—C5—O3 | −175.4 (2) | HC18—C18—C19—C20 | −179.2 |
C6—N1—C5—O4 | 5.5 (5) | HC18—C18—C19—HC19 | 0.8 |
C1—N1—C6—C7 | 161.7 (3) | C18—C19—C20—C21 | −0.6 (7) |
C1—N1—C6—C11 | −16.8 (4) | C18—C19—C20—HC20 | 179.4 |
C5—N1—C6—C7 | −30.7 (4) | HC19—C19—C20—C21 | 179.4 |
C5—N1—C6—C11 | 150.8 (3) | HC19—C19—C20—HC20 | −0.6 |
O5—N2—C9—C8 | 160.6 (4) | C19—C20—C21—C22 | −0.5 (8) |
O5—N2—C9—C10 | −20.7 (5) | C19—C20—C21—HC21 | 179.5 |
O6—N2—C9—C8 | −19.9 (6) | HC20—C20—C21—C22 | 179.5 |
O6—N2—C9—C10 | 158.8 (4) | HC20—C20—C21—HC21 | −0.5 |
N1—C1—C2—C3 | 112.2 (3) | C20—C21—C22—C17 | 1.3 (7) |
N1—C1—C2—H1C2 | −7.3 | C20—C21—C22—HC22 | −178.7 |
N1—C1—C2—H2C2 | −128.3 | HC21—C21—C22—C17 | −178.7 |
C4—C1—C2—C3 | 2.9 (3) | HC21—C21—C22—HC22 | 1.3 |
C4—C1—C2—H1C2 | −116.6 | Si—C25—C26—H1C26 | −180.0 |
C4—C1—C2—H2C2 | 122.4 | Si—C25—C26—H2C26 | −60.0 |
C12—C1—C2—C3 | −116.1 (2) | Si—C25—C26—H3C26 | 60.0 |
C12—C1—C2—H1C2 | 124.4 | C27—C25—C26—H1C26 | 56.9 |
C12—C1—C2—H2C2 | 3.3 | C27—C25—C26—H2C26 | 176.9 |
N1—C1—C4—O2 | −121.2 (2) | C27—C25—C26—H3C26 | −63.1 |
N1—C1—C4—O3 | −4.2 (3) | C28—C25—C26—H1C26 | −62.0 |
N1—C1—C4—HC4 | 116.7 | C28—C25—C26—H2C26 | 58.0 |
C2—C1—C4—O2 | −2.5 (3) | C28—C25—C26—H3C26 | 178.0 |
C2—C1—C4—O3 | 114.6 (2) | Si—C25—C27—H1C27 | −180.0 |
C2—C1—C4—HC4 | −124.5 | Si—C25—C27—H2C27 | −60.0 |
C12—C1—C4—O2 | 118.7 (2) | Si—C25—C27—H3C27 | 60.0 |
C12—C1—C4—O3 | −124.2 (2) | C26—C25—C27—H1C27 | −56.7 |
C12—C1—C4—HC4 | −3.4 | C26—C25—C27—H2C27 | 63.3 |
N1—C1—C12—O9 | −168.4 (2) | C26—C25—C27—H3C27 | −176.7 |
N1—C1—C12—C13 | −46.1 (3) | C28—C25—C27—H1C27 | 60.4 |
N1—C1—C12—HC12 | 74.8 | C28—C25—C27—H2C27 | −179.6 |
C2—C1—C12—O9 | 59.2 (3) | C28—C25—C27—H3C27 | −59.6 |
C2—C1—C12—C13 | −178.5 (2) | Si—C25—C28—H1C28 | 180.0 |
C2—C1—C12—HC12 | −57.6 | Si—C25—C28—H2C28 | −60.0 |
C4—C1—C12—O9 | −55.7 (3) | Si—C25—C28—H3C28 | 60.0 |
C4—C1—C12—C13 | 66.6 (3) | C26—C25—C28—H1C28 | 59.7 |
C4—C1—C12—HC12 | −172.5 | C26—C25—C28—H2C28 | 179.7 |
C1—C2—C3—O1 | 177.0 (3) | C26—C25—C28—H3C28 | −60.3 |
C1—C2—C3—O2 | −2.5 (3) | C27—C25—C28—H1C28 | −58.5 |
H1C2—C2—C3—O1 | −63.6 | C27—C25—C28—H2C28 | 61.5 |
H1C2—C2—C3—O2 | 116.9 | C27—C25—C28—H3C28 | −178.5 |
Experimental details
Crystal data | |
Chemical formula | C28H32N2O9Si |
Mr | 568.7 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 9.680 (3), 11.674 (5), 13.565 (6) |
α, β, γ (°) | 88.75 (3), 79.74 (2), 77.13 (3) |
V (Å3) | 1470.2 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.25 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5435, 5155, 3251 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.056, 1.63 |
No. of reflections | 3251 |
No. of parameters | 349 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.31 |
Computer programs: CAD-4 Software (Schagen et al., 1989), CAD-4 Software, SIR92 (Altomare et al., 1994), RAELS (Rae, 1996), ORTEPII (Johnson, 1976), local programs.
We have reported a facile synthesis of alpha-substituted gamma- hydroxybutenolides (Patil & Liu, 2007). In an effort to trap the epimerizable gamma-hydroxy group of butenolide, (I), using an isocyanate, (II), we report the synthesis and structure of the title compound, (III). This molecule contains a substituted dihydro-1H-furo[3,2-d]oxazole-2,5-dione ring, which is a new bicyclic oxazole-dione ring.