Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001228/ob6110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001228/ob6110Isup2.hkl |
CCDC reference: 180810
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.009 Å
- R factor = 0.082
- wR factor = 0.254
- Data-to-parameter ratio = 13.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 3107 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3598 Completeness (_total/calc) 86.35% Alert B: < 90% complete (theta max?)
Alert Level C:
RFACR_01 Alert C The value of the weighted R factor is > 0.25 Weighted R factor given 0.254 RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.103 PLAT_213 Alert C Atom C14 has ADP max/min Ratio ........... 3.30 prolate PLAT_213 Alert C Atom C19 has ADP max/min Ratio ........... 3.40 prolate PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(12) - C(14) = 1.35 Ang.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
5 Alert Level C = Please check
Data collection: DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO, COLLECT (Hooft, 1998) and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).
C20H31NO3Si | F(000) = 1568 |
Mr = 361.55 | Dx = 1.181 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.6339 (3) Å | Cell parameters from 3107 reflections |
b = 7.7463 (1) Å | θ = 3.0–25.0° |
c = 35.8752 (7) Å | µ = 0.13 mm−1 |
β = 91.066 (3)° | T = 120 K |
V = 4066.06 (13) Å3 | Needle, colourless |
Z = 8 | 0.15 × 0.07 × 0.06 mm |
Nonius KappaCCD area-detector diffractometer | 3107 independent reflections |
Radiation source: Bruker Nonius FR591 rotating anode | 1445 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.103 |
Detector resolution: 9.091 pixels/mm pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
Φ and ω scans to fill asymmetric unit | h = −17→17 |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | k = −8→8 |
Tmin = 0.980, Tmax = 0.992 | l = −42→42 |
6912 measured reflections |
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)] = 0.082 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.254 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.13P)2] where P = (Fo2 + 2Fc2)/3 |
3107 reflections | (Δ/σ)max = 0.002 |
226 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.58 e Å−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 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 | ||
N1 | 0.5727 (3) | −0.7427 (7) | 0.79405 (15) | 0.0323 (13) | |
O1 | 0.5776 (3) | −0.8886 (5) | 0.78142 (11) | 0.0428 (12) | |
O2 | 0.5447 (3) | −0.7108 (5) | 0.82524 (12) | 0.0431 (12) | |
O3 | 0.7483 (3) | −0.2272 (4) | 0.67730 (10) | 0.0328 (11) | |
Si1 | 0.68995 (13) | 0.2141 (2) | 0.58388 (5) | 0.0375 (6) | |
C1 | 0.6186 (4) | −0.2955 (7) | 0.76192 (15) | 0.0312 (16) | |
H1 | 0.6138 | −0.1806 | 0.7709 | 0.037* | |
C2 | 0.5926 (4) | −0.4319 (7) | 0.78403 (16) | 0.0302 (15) | |
H2 | 0.5689 | −0.4121 | 0.8081 | 0.036* | |
C3 | 0.6015 (4) | −0.5961 (7) | 0.77061 (16) | 0.0263 (14) | |
C4 | 0.6352 (4) | −0.6308 (7) | 0.73596 (16) | 0.0299 (15) | |
H4 | 0.6413 | −0.7464 | 0.7275 | 0.036* | |
C5 | 0.6600 (4) | −0.4950 (7) | 0.71375 (16) | 0.0312 (16) | |
H5 | 0.6829 | −0.5166 | 0.6896 | 0.037* | |
C6 | 0.6519 (4) | −0.3257 (7) | 0.72634 (16) | 0.0282 (15) | |
C7 | 0.6765 (4) | −0.1750 (7) | 0.70137 (16) | 0.0304 (15) | |
H7 | 0.6980 | −0.0761 | 0.7172 | 0.036* | |
C8 | 0.6009 (4) | −0.1134 (7) | 0.67492 (15) | 0.0338 (16) | |
H8A | 0.5650 | −0.2114 | 0.6647 | 0.041* | |
H8B | 0.5593 | −0.0318 | 0.6874 | 0.041* | |
C9 | 0.6551 (4) | −0.0245 (7) | 0.64485 (15) | 0.0276 (15) | |
C10 | 0.7487 (4) | −0.1048 (7) | 0.64699 (16) | 0.0351 (16) | |
H10A | 0.7624 | −0.1640 | 0.6233 | 0.042* | |
H10B | 0.7957 | −0.0151 | 0.6516 | 0.042* | |
C11 | 0.6272 (4) | 0.0973 (8) | 0.62150 (15) | 0.0369 (16) | |
H11 | 0.5653 | 0.1314 | 0.6242 | 0.044* | |
C12 | 0.6177 (5) | 0.4071 (8) | 0.57111 (18) | 0.057 (2) | |
H12 | 0.6611 | 0.4795 | 0.5566 | 0.068* | |
C13 | 0.5966 (5) | 0.5234 (8) | 0.60428 (17) | 0.053 (2) | |
H13A | 0.6523 | 0.5407 | 0.6194 | 0.079* | |
H13B | 0.5497 | 0.4689 | 0.6195 | 0.079* | |
H13C | 0.5742 | 0.6353 | 0.5952 | 0.079* | |
C14 | 0.5464 (10) | 0.3907 (15) | 0.5471 (3) | 0.216 (9) | |
H14A | 0.5639 | 0.3168 | 0.5262 | 0.324* | |
H14B | 0.5287 | 0.5048 | 0.5377 | 0.324* | |
H14C | 0.4947 | 0.3385 | 0.5600 | 0.324* | |
C15 | 0.8096 (4) | 0.2760 (8) | 0.59925 (16) | 0.0422 (18) | |
H15 | 0.8457 | 0.1665 | 0.6004 | 0.051* | |
C16 | 0.8196 (4) | 0.3606 (7) | 0.63799 (16) | 0.0437 (18) | |
H16A | 0.7913 | 0.2865 | 0.6567 | 0.066* | |
H16B | 0.7893 | 0.4734 | 0.6377 | 0.066* | |
H16C | 0.8846 | 0.3758 | 0.6443 | 0.066* | |
C17 | 0.8567 (5) | 0.3929 (10) | 0.57045 (18) | 0.066 (2) | |
H17A | 0.8516 | 0.3400 | 0.5457 | 0.099* | |
H17B | 0.9213 | 0.4067 | 0.5774 | 0.099* | |
H17C | 0.8269 | 0.5063 | 0.5700 | 0.099* | |
C18 | 0.6989 (5) | 0.0710 (8) | 0.54094 (16) | 0.0448 (18) | |
H18 | 0.7060 | 0.1500 | 0.5191 | 0.054* | |
C19 | 0.7813 (7) | −0.0489 (13) | 0.5413 (2) | 0.139 (5) | |
H19A | 0.8371 | 0.0186 | 0.5458 | 0.209* | |
H19B | 0.7850 | −0.1078 | 0.5172 | 0.209* | |
H19C | 0.7749 | −0.1346 | 0.5612 | 0.209* | |
C20 | 0.6128 (6) | −0.0332 (10) | 0.53349 (19) | 0.078 (3) | |
H20A | 0.5598 | 0.0441 | 0.5329 | 0.118* | |
H20B | 0.6056 | −0.1187 | 0.5534 | 0.118* | |
H20C | 0.6175 | −0.0925 | 0.5095 | 0.118* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.016 (3) | 0.039 (3) | 0.042 (3) | 0.002 (3) | 0.001 (3) | −0.002 (3) |
O1 | 0.044 (3) | 0.034 (3) | 0.051 (3) | −0.006 (2) | 0.001 (2) | 0.001 (2) |
O2 | 0.034 (3) | 0.048 (3) | 0.048 (3) | −0.001 (2) | 0.011 (2) | 0.003 (2) |
O3 | 0.023 (3) | 0.033 (2) | 0.043 (3) | 0.004 (2) | 0.006 (2) | 0.0083 (19) |
Si1 | 0.0382 (13) | 0.0451 (11) | 0.0295 (10) | 0.0058 (9) | 0.0051 (9) | 0.0031 (8) |
C1 | 0.032 (4) | 0.025 (3) | 0.036 (4) | 0.008 (3) | −0.004 (3) | −0.002 (3) |
C2 | 0.025 (4) | 0.031 (4) | 0.035 (4) | 0.003 (3) | 0.003 (3) | −0.003 (3) |
C3 | 0.027 (4) | 0.018 (3) | 0.034 (4) | −0.001 (3) | 0.001 (3) | 0.003 (3) |
C4 | 0.021 (4) | 0.028 (3) | 0.040 (4) | 0.005 (3) | −0.005 (3) | 0.002 (3) |
C5 | 0.029 (4) | 0.033 (4) | 0.031 (4) | 0.004 (3) | −0.001 (3) | −0.002 (3) |
C6 | 0.013 (4) | 0.034 (4) | 0.037 (4) | −0.001 (3) | −0.004 (3) | 0.000 (3) |
C7 | 0.020 (4) | 0.032 (3) | 0.039 (4) | 0.000 (3) | 0.004 (3) | −0.002 (3) |
C8 | 0.019 (4) | 0.043 (4) | 0.040 (4) | 0.007 (3) | 0.005 (3) | −0.004 (3) |
C9 | 0.019 (4) | 0.031 (3) | 0.033 (4) | 0.000 (3) | 0.005 (3) | −0.004 (3) |
C10 | 0.027 (4) | 0.032 (4) | 0.046 (4) | 0.003 (3) | 0.004 (3) | 0.012 (3) |
C11 | 0.028 (4) | 0.046 (4) | 0.037 (4) | 0.007 (3) | 0.000 (3) | −0.002 (3) |
C12 | 0.075 (6) | 0.061 (5) | 0.034 (4) | 0.025 (4) | −0.006 (4) | 0.010 (4) |
C13 | 0.063 (6) | 0.048 (4) | 0.047 (4) | 0.013 (4) | 0.005 (4) | 0.007 (3) |
C14 | 0.33 (2) | 0.188 (12) | 0.122 (9) | 0.184 (14) | −0.142 (12) | −0.090 (9) |
C15 | 0.045 (5) | 0.044 (4) | 0.038 (4) | 0.001 (4) | 0.006 (3) | 0.003 (3) |
C16 | 0.045 (5) | 0.045 (4) | 0.042 (4) | −0.002 (4) | 0.003 (3) | 0.005 (3) |
C17 | 0.036 (5) | 0.110 (6) | 0.053 (5) | −0.017 (5) | 0.008 (4) | 0.020 (4) |
C18 | 0.056 (5) | 0.048 (4) | 0.031 (4) | −0.003 (4) | 0.005 (4) | 0.000 (3) |
C19 | 0.170 (11) | 0.162 (10) | 0.085 (7) | 0.115 (9) | −0.033 (7) | −0.073 (7) |
C20 | 0.104 (8) | 0.076 (5) | 0.057 (5) | −0.034 (5) | 0.032 (5) | −0.019 (4) |
N1—O1 | 1.220 (5) | C11—H11 | 0.9500 |
N1—O2 | 1.224 (6) | C12—C14 | 1.346 (11) |
N1—C3 | 1.479 (7) | C12—C13 | 1.529 (8) |
O3—C7 | 1.432 (6) | C12—H12 | 1.0000 |
O3—C10 | 1.443 (6) | C13—H13A | 0.9800 |
Si1—C11 | 1.879 (6) | C13—H13B | 0.9800 |
Si1—C12 | 1.882 (7) | C13—H13C | 0.9800 |
Si1—C15 | 1.888 (7) | C14—H14A | 0.9800 |
Si1—C18 | 1.904 (6) | C14—H14B | 0.9800 |
C1—C2 | 1.379 (7) | C14—H14C | 0.9800 |
C1—C6 | 1.395 (7) | C15—C16 | 1.541 (8) |
C1—H1 | 0.9500 | C15—C17 | 1.545 (8) |
C2—C3 | 1.367 (7) | C15—H15 | 1.0000 |
C2—H2 | 0.9500 | C16—H16A | 0.9800 |
C3—C4 | 1.372 (7) | C16—H16B | 0.9800 |
C4—C5 | 1.372 (7) | C16—H16C | 0.9800 |
C4—H4 | 0.9500 | C17—H17A | 0.9800 |
C5—C6 | 1.392 (7) | C17—H17B | 0.9800 |
C5—H5 | 0.9500 | C17—H17C | 0.9800 |
C6—C7 | 1.518 (8) | C18—C20 | 1.516 (9) |
C7—C8 | 1.521 (8) | C18—C19 | 1.522 (9) |
C7—H7 | 1.0000 | C18—H18 | 1.0000 |
C8—C9 | 1.517 (7) | C19—H19A | 0.9800 |
C8—H8A | 0.9900 | C19—H19B | 0.9800 |
C8—H8B | 0.9900 | C19—H19C | 0.9800 |
C9—C11 | 1.322 (7) | C20—H20A | 0.9800 |
C9—C10 | 1.504 (7) | C20—H20B | 0.9800 |
C10—H10A | 0.9900 | C20—H20C | 0.9800 |
C10—H10B | 0.9900 | ||
O1—N1—O2 | 123.3 (5) | C14—C12—Si1 | 120.4 (7) |
O1—N1—C3 | 118.7 (5) | C13—C12—Si1 | 113.6 (4) |
O2—N1—C3 | 118.0 (5) | C14—C12—H12 | 102.3 |
C7—O3—C10 | 106.4 (4) | C13—C12—H12 | 102.3 |
C11—Si1—C12 | 106.1 (3) | Si1—C12—H12 | 102.3 |
C11—Si1—C15 | 112.1 (3) | C12—C13—H13A | 109.5 |
C12—Si1—C15 | 112.5 (3) | C12—C13—H13B | 109.5 |
C11—Si1—C18 | 110.1 (3) | H13A—C13—H13B | 109.5 |
C12—Si1—C18 | 108.2 (3) | C12—C13—H13C | 109.5 |
C15—Si1—C18 | 107.9 (3) | H13A—C13—H13C | 109.5 |
C2—C1—C6 | 120.2 (5) | H13B—C13—H13C | 109.5 |
C2—C1—H1 | 119.9 | C12—C14—H14A | 109.5 |
C6—C1—H1 | 119.9 | C12—C14—H14B | 109.5 |
C3—C2—C1 | 118.8 (5) | H14A—C14—H14B | 109.5 |
C3—C2—H2 | 120.6 | C12—C14—H14C | 109.5 |
C1—C2—H2 | 120.6 | H14A—C14—H14C | 109.5 |
C2—C3—C4 | 122.6 (5) | H14B—C14—H14C | 109.5 |
C2—C3—N1 | 118.9 (5) | C16—C15—C17 | 108.5 (5) |
C4—C3—N1 | 118.4 (5) | C16—C15—Si1 | 116.3 (4) |
C3—C4—C5 | 118.6 (5) | C17—C15—Si1 | 112.1 (4) |
C3—C4—H4 | 120.7 | C16—C15—H15 | 106.4 |
C5—C4—H4 | 120.7 | C17—C15—H15 | 106.4 |
C4—C5—C6 | 120.6 (5) | Si1—C15—H15 | 106.4 |
C4—C5—H5 | 119.7 | C15—C16—H16A | 109.5 |
C6—C5—H5 | 119.7 | C15—C16—H16B | 109.5 |
C5—C6—C1 | 119.2 (5) | H16A—C16—H16B | 109.5 |
C5—C6—C7 | 120.7 (5) | C15—C16—H16C | 109.5 |
C1—C6—C7 | 120.1 (5) | H16A—C16—H16C | 109.5 |
O3—C7—C6 | 108.8 (4) | H16B—C16—H16C | 109.5 |
O3—C7—C8 | 104.2 (4) | C15—C17—H17A | 109.5 |
C6—C7—C8 | 115.6 (5) | C15—C17—H17B | 109.5 |
O3—C7—H7 | 109.3 | H17A—C17—H17B | 109.5 |
C6—C7—H7 | 109.3 | C15—C17—H17C | 109.5 |
C8—C7—H7 | 109.3 | H17A—C17—H17C | 109.5 |
C9—C8—C7 | 101.7 (5) | H17B—C17—H17C | 109.5 |
C9—C8—H8A | 111.4 | C20—C18—C19 | 109.4 (7) |
C7—C8—H8A | 111.4 | C20—C18—Si1 | 112.5 (5) |
C9—C8—H8B | 111.4 | C19—C18—Si1 | 114.5 (5) |
C7—C8—H8B | 111.4 | C20—C18—H18 | 106.6 |
H8A—C8—H8B | 109.3 | C19—C18—H18 | 106.6 |
C11—C9—C10 | 126.8 (5) | Si1—C18—H18 | 106.6 |
C11—C9—C8 | 127.9 (6) | C18—C19—H19A | 109.5 |
C10—C9—C8 | 105.3 (5) | C18—C19—H19B | 109.5 |
O3—C10—C9 | 107.1 (5) | H19A—C19—H19B | 109.5 |
O3—C10—H10A | 110.3 | C18—C19—H19C | 109.5 |
C9—C10—H10A | 110.3 | H19A—C19—H19C | 109.5 |
O3—C10—H10B | 110.3 | H19B—C19—H19C | 109.5 |
C9—C10—H10B | 110.3 | C18—C20—H20A | 109.5 |
H10A—C10—H10B | 108.6 | C18—C20—H20B | 109.5 |
C9—C11—Si1 | 130.5 (5) | H20A—C20—H20B | 109.5 |
C9—C11—H11 | 114.8 | C18—C20—H20C | 109.5 |
Si1—C11—H11 | 114.8 | H20A—C20—H20C | 109.5 |
C14—C12—C13 | 112.8 (7) | H20B—C20—H20C | 109.5 |
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