Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001137/ob6109sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001137/ob6109Isup2.hkl |
CCDC reference: 182608
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.081
- Data-to-parameter ratio = 14.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 4610 Count of symmetry unique reflns 2636 Completeness (_total/calc) 174.89% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1974 Fraction of Friedel pairs measured 0.749 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
The synthesis of the title compound were carried out by the BF3·Et2O-mediated addition of triisopropyl(2-methylidenecyclopropyl)silane to 4-nitrobenzaldehyde in dichloromethane in 29% yield.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO, COLLECT 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).
C27H36N2O6Si | Dx = 1.294 Mg m−3 |
Mr = 512.67 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4610 reflections |
a = 11.4829 (3) Å | θ = 2.9–25.0° |
b = 14.5419 (3) Å | µ = 0.13 mm−1 |
c = 15.7595 (4) Å | T = 120 K |
V = 2631.57 (11) Å3 | Block, colourless |
Z = 4 | 0.2 × 0.15 × 0.1 mm |
F(000) = 1096 |
Nonius KappaCCD area-detector diffractometer | 4610 independent reflections |
Radiation source: Bruker Nonius FR591 rotating anode | 4150 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 9.091 pixels/mm pixels mm-1 | θmax = 25.0°, θmin = 2.9° |
Φ and ω scans to fill asymmetric unit | h = −13→13 |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | k = −17→17 |
Tmin = 0.974, Tmax = 0.987 | l = −18→18 |
14158 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0435P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.081 | (Δ/σ)max = 0.011 |
S = 1.08 | Δρmax = 0.28 e Å−3 |
4610 reflections | Δρmin = −0.19 e Å−3 |
326 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0054 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1974 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.04 (11) |
C27H36N2O6Si | V = 2631.57 (11) Å3 |
Mr = 512.67 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 11.4829 (3) Å | µ = 0.13 mm−1 |
b = 14.5419 (3) Å | T = 120 K |
c = 15.7595 (4) Å | 0.2 × 0.15 × 0.1 mm |
Nonius KappaCCD area-detector diffractometer | 4610 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 4150 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.987 | Rint = 0.043 |
14158 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.081 | Δρmax = 0.28 e Å−3 |
S = 1.08 | Δρmin = −0.19 e Å−3 |
4610 reflections | Absolute structure: Flack (1983), 1974 Friedel pairs |
326 parameters | Absolute structure parameter: −0.04 (11) |
0 restraints |
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 | ||
C1 | 0.24588 (18) | 0.30746 (12) | 0.55009 (12) | 0.0181 (4) | |
C2 | 0.31673 (18) | 0.37229 (13) | 0.58709 (13) | 0.0215 (5) | |
H2 | 0.3841 | 0.3543 | 0.6178 | 0.026* | |
C3 | 0.28775 (18) | 0.46467 (13) | 0.57859 (12) | 0.0203 (4) | |
H3 | 0.3357 | 0.5104 | 0.6038 | 0.024* | |
C4 | 0.18880 (17) | 0.49060 (13) | 0.53334 (12) | 0.0170 (4) | |
C5 | 0.11883 (18) | 0.42272 (13) | 0.49717 (12) | 0.0207 (4) | |
H5 | 0.0510 | 0.4400 | 0.4665 | 0.025* | |
C6 | 0.14686 (18) | 0.33031 (13) | 0.50535 (12) | 0.0208 (5) | |
H6 | 0.0991 | 0.2841 | 0.4808 | 0.025* | |
C7 | 0.15625 (16) | 0.59048 (12) | 0.52233 (12) | 0.0164 (4) | |
H7 | 0.1385 | 0.6026 | 0.4612 | 0.020* | |
C8 | 0.05374 (17) | 0.62342 (12) | 0.57714 (12) | 0.0173 (4) | |
H8A | 0.0488 | 0.5872 | 0.6302 | 0.021* | |
H8B | −0.0207 | 0.6172 | 0.5459 | 0.021* | |
C9 | 0.07986 (16) | 0.72624 (12) | 0.59682 (11) | 0.0159 (4) | |
C10 | 0.01647 (17) | 0.79106 (13) | 0.53383 (12) | 0.0181 (4) | |
H10A | −0.0604 | 0.7658 | 0.5175 | 0.022* | |
H10B | 0.0054 | 0.8529 | 0.5587 | 0.022* | |
C11 | 0.09817 (16) | 0.79477 (13) | 0.45799 (12) | 0.0175 (4) | |
H11 | 0.0887 | 0.7376 | 0.4234 | 0.021* | |
C12 | 0.20914 (17) | 0.73603 (13) | 0.56837 (11) | 0.0170 (4) | |
H12 | 0.2562 | 0.7633 | 0.6155 | 0.020* | |
C13 | 0.08396 (16) | 0.87798 (12) | 0.40158 (12) | 0.0171 (4) | |
C14 | 0.12278 (18) | 0.96456 (13) | 0.42599 (13) | 0.0210 (5) | |
H14 | 0.1595 | 0.9726 | 0.4795 | 0.025* | |
C15 | 0.10802 (18) | 1.03917 (13) | 0.37240 (14) | 0.0239 (5) | |
H15 | 0.1339 | 1.0987 | 0.3887 | 0.029* | |
C16 | 0.05479 (17) | 1.02531 (13) | 0.29475 (13) | 0.0218 (4) | |
C17 | 0.01480 (17) | 0.94038 (13) | 0.26911 (13) | 0.0215 (5) | |
H17 | −0.0215 | 0.9325 | 0.2154 | 0.026* | |
C18 | 0.02910 (17) | 0.86714 (13) | 0.32398 (13) | 0.0205 (4) | |
H18 | 0.0008 | 0.8082 | 0.3082 | 0.025* | |
C19 | 0.09741 (18) | 0.66025 (13) | 0.78274 (12) | 0.0213 (4) | |
H19 | 0.0538 | 0.6054 | 0.7613 | 0.026* | |
C20 | 0.0647 (2) | 0.67037 (17) | 0.87670 (13) | 0.0352 (6) | |
H20A | −0.0182 | 0.6856 | 0.8815 | 0.053* | |
H20B | 0.1113 | 0.7196 | 0.9023 | 0.053* | |
H20C | 0.0802 | 0.6124 | 0.9064 | 0.053* | |
C21 | 0.22669 (18) | 0.63654 (15) | 0.77507 (14) | 0.0267 (5) | |
H21A | 0.2470 | 0.6289 | 0.7151 | 0.040* | |
H21B | 0.2425 | 0.5792 | 0.8056 | 0.040* | |
H21C | 0.2734 | 0.6863 | 0.7996 | 0.040* | |
C22 | −0.10770 (17) | 0.78267 (13) | 0.73423 (12) | 0.0217 (5) | |
H22 | −0.1124 | 0.7977 | 0.7960 | 0.026* | |
C23 | −0.18196 (18) | 0.69638 (15) | 0.72297 (15) | 0.0304 (5) | |
H23A | −0.1447 | 0.6446 | 0.7521 | 0.046* | |
H23B | −0.1894 | 0.6823 | 0.6624 | 0.046* | |
H23C | −0.2594 | 0.7069 | 0.7472 | 0.046* | |
C24 | −0.16472 (18) | 0.86470 (16) | 0.68855 (14) | 0.0306 (5) | |
H24A | −0.1166 | 0.9197 | 0.6964 | 0.046* | |
H24B | −0.2424 | 0.8756 | 0.7123 | 0.046* | |
H24C | −0.1715 | 0.8511 | 0.6279 | 0.046* | |
C25 | 0.14086 (18) | 0.86623 (13) | 0.74331 (12) | 0.0212 (4) | |
H25 | 0.2197 | 0.8430 | 0.7596 | 0.025* | |
C26 | 0.0912 (2) | 0.91336 (15) | 0.82286 (14) | 0.0321 (5) | |
H26A | 0.0783 | 0.8673 | 0.8673 | 0.048* | |
H26B | 0.0171 | 0.9431 | 0.8087 | 0.048* | |
H26C | 0.1465 | 0.9597 | 0.8433 | 0.048* | |
C27 | 0.1611 (2) | 0.93941 (14) | 0.67450 (14) | 0.0275 (5) | |
H27A | 0.1931 | 0.9101 | 0.6236 | 0.041* | |
H27B | 0.2161 | 0.9856 | 0.6955 | 0.041* | |
H27C | 0.0870 | 0.9692 | 0.6605 | 0.041* | |
N1 | 0.28088 (16) | 0.20983 (11) | 0.55630 (11) | 0.0237 (4) | |
N2 | 0.04039 (15) | 1.10398 (12) | 0.23780 (13) | 0.0305 (4) | |
O1 | 0.37431 (14) | 0.19131 (10) | 0.58978 (11) | 0.0350 (4) | |
O2 | 0.21487 (14) | 0.15148 (10) | 0.52703 (11) | 0.0373 (4) | |
O3 | 0.05978 (15) | 1.18119 (10) | 0.26650 (12) | 0.0455 (5) | |
O4 | 0.00971 (16) | 1.09004 (12) | 0.16447 (11) | 0.0468 (5) | |
O5 | 0.25208 (11) | 0.64728 (8) | 0.54841 (8) | 0.0180 (3) | |
O6 | 0.21199 (11) | 0.79525 (9) | 0.49660 (8) | 0.0179 (3) | |
Si1 | 0.05191 (5) | 0.76050 (3) | 0.71299 (3) | 0.01668 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0241 (11) | 0.0119 (9) | 0.0181 (10) | 0.0022 (8) | 0.0072 (9) | −0.0008 (8) |
C2 | 0.0235 (12) | 0.0210 (11) | 0.0201 (10) | 0.0003 (9) | −0.0010 (9) | 0.0006 (9) |
C3 | 0.0228 (11) | 0.0169 (10) | 0.0213 (10) | −0.0015 (8) | −0.0007 (9) | −0.0015 (8) |
C4 | 0.0223 (11) | 0.0164 (10) | 0.0123 (9) | −0.0007 (8) | 0.0036 (8) | −0.0003 (8) |
C5 | 0.0220 (11) | 0.0224 (11) | 0.0176 (10) | 0.0006 (8) | 0.0005 (9) | −0.0003 (9) |
C6 | 0.0219 (11) | 0.0191 (10) | 0.0215 (10) | −0.0049 (8) | 0.0046 (9) | −0.0053 (9) |
C7 | 0.0177 (10) | 0.0174 (10) | 0.0139 (9) | −0.0020 (8) | 0.0003 (8) | −0.0011 (8) |
C8 | 0.0174 (10) | 0.0182 (10) | 0.0161 (9) | −0.0025 (8) | 0.0013 (9) | −0.0013 (8) |
C9 | 0.0142 (10) | 0.0178 (10) | 0.0157 (9) | 0.0002 (7) | 0.0001 (8) | 0.0006 (8) |
C10 | 0.0184 (11) | 0.0197 (10) | 0.0160 (9) | 0.0003 (8) | −0.0022 (8) | −0.0003 (8) |
C11 | 0.0197 (11) | 0.0149 (10) | 0.0178 (10) | 0.0003 (8) | −0.0008 (8) | −0.0003 (8) |
C12 | 0.0211 (11) | 0.0139 (9) | 0.0159 (9) | 0.0006 (8) | 0.0013 (8) | 0.0008 (8) |
C13 | 0.0184 (11) | 0.0148 (10) | 0.0182 (10) | 0.0025 (8) | 0.0041 (8) | 0.0015 (8) |
C14 | 0.0243 (12) | 0.0193 (11) | 0.0193 (10) | −0.0019 (9) | −0.0029 (9) | 0.0009 (8) |
C15 | 0.0233 (11) | 0.0169 (10) | 0.0315 (12) | −0.0024 (9) | −0.0032 (10) | 0.0014 (9) |
C16 | 0.0172 (10) | 0.0203 (10) | 0.0279 (11) | 0.0022 (9) | 0.0026 (9) | 0.0096 (9) |
C17 | 0.0206 (11) | 0.0248 (11) | 0.0189 (10) | 0.0015 (8) | −0.0025 (9) | 0.0017 (9) |
C18 | 0.0208 (11) | 0.0185 (10) | 0.0222 (10) | −0.0019 (8) | −0.0015 (9) | −0.0011 (9) |
C19 | 0.0236 (11) | 0.0239 (10) | 0.0165 (10) | −0.0017 (8) | −0.0030 (9) | −0.0008 (9) |
C20 | 0.0375 (14) | 0.0486 (15) | 0.0194 (11) | 0.0095 (11) | −0.0011 (10) | 0.0076 (10) |
C21 | 0.0248 (12) | 0.0267 (10) | 0.0286 (12) | 0.0023 (9) | −0.0026 (10) | 0.0070 (10) |
C22 | 0.0182 (11) | 0.0315 (11) | 0.0155 (10) | 0.0034 (9) | 0.0007 (8) | −0.0030 (8) |
C23 | 0.0207 (12) | 0.0411 (13) | 0.0293 (12) | −0.0052 (10) | 0.0000 (10) | −0.0009 (11) |
C24 | 0.0208 (12) | 0.0436 (13) | 0.0275 (12) | 0.0125 (10) | 0.0016 (10) | −0.0014 (10) |
C25 | 0.0196 (11) | 0.0226 (10) | 0.0215 (10) | 0.0006 (8) | −0.0016 (9) | −0.0047 (9) |
C26 | 0.0370 (14) | 0.0316 (12) | 0.0278 (11) | 0.0013 (10) | −0.0015 (11) | −0.0131 (10) |
C27 | 0.0319 (13) | 0.0201 (11) | 0.0306 (12) | −0.0025 (9) | −0.0019 (10) | −0.0037 (10) |
N1 | 0.0284 (11) | 0.0193 (9) | 0.0234 (9) | 0.0012 (8) | 0.0057 (8) | −0.0013 (7) |
N2 | 0.0189 (10) | 0.0299 (11) | 0.0428 (12) | −0.0001 (8) | −0.0028 (9) | 0.0184 (9) |
O1 | 0.0315 (10) | 0.0229 (8) | 0.0506 (10) | 0.0066 (7) | −0.0021 (8) | 0.0029 (8) |
O2 | 0.0450 (10) | 0.0170 (7) | 0.0499 (10) | −0.0040 (7) | −0.0044 (8) | −0.0083 (7) |
O3 | 0.0451 (11) | 0.0230 (9) | 0.0684 (12) | −0.0070 (7) | −0.0170 (10) | 0.0192 (9) |
O4 | 0.0561 (12) | 0.0480 (11) | 0.0364 (10) | 0.0013 (9) | −0.0134 (9) | 0.0239 (9) |
O5 | 0.0163 (7) | 0.0143 (6) | 0.0233 (7) | 0.0002 (6) | 0.0022 (6) | 0.0004 (6) |
O6 | 0.0169 (7) | 0.0176 (7) | 0.0192 (7) | 0.0000 (5) | 0.0021 (6) | 0.0052 (6) |
Si1 | 0.0156 (3) | 0.0203 (3) | 0.0141 (3) | 0.0008 (2) | −0.0006 (2) | −0.0016 (2) |
C1—C2 | 1.375 (3) | C17—C18 | 1.382 (3) |
C1—C6 | 1.379 (3) | C17—H17 | 0.9500 |
C1—N1 | 1.479 (2) | C18—H18 | 0.9500 |
C2—C3 | 1.390 (3) | C19—C21 | 1.529 (3) |
C2—H2 | 0.9500 | C19—C20 | 1.535 (3) |
C3—C4 | 1.393 (3) | C19—Si1 | 1.899 (2) |
C3—H3 | 0.9500 | C19—H19 | 1.0000 |
C4—C5 | 1.395 (3) | C20—H20A | 0.9800 |
C4—C7 | 1.510 (3) | C20—H20B | 0.9800 |
C5—C6 | 1.388 (3) | C20—H20C | 0.9800 |
C5—H5 | 0.9500 | C21—H21A | 0.9800 |
C6—H6 | 0.9500 | C21—H21B | 0.9800 |
C7—O5 | 1.436 (2) | C21—H21C | 0.9800 |
C7—C8 | 1.537 (3) | C22—C23 | 1.527 (3) |
C7—H7 | 1.0000 | C22—C24 | 1.539 (3) |
C8—C9 | 1.556 (3) | C22—Si1 | 1.891 (2) |
C8—H8A | 0.9900 | C22—H22 | 1.0000 |
C8—H8B | 0.9900 | C23—H23A | 0.9800 |
C9—C10 | 1.550 (3) | C23—H23B | 0.9800 |
C9—C12 | 1.557 (3) | C23—H23C | 0.9800 |
C9—Si1 | 1.9244 (19) | C24—H24A | 0.9800 |
C10—C11 | 1.520 (3) | C24—H24B | 0.9800 |
C10—H10A | 0.9900 | C24—H24C | 0.9800 |
C10—H10B | 0.9900 | C25—C26 | 1.538 (3) |
C11—O6 | 1.442 (2) | C25—C27 | 1.537 (3) |
C11—C13 | 1.510 (3) | C25—Si1 | 1.907 (2) |
C11—H11 | 1.0000 | C25—H25 | 1.0000 |
C12—O5 | 1.417 (2) | C26—H26A | 0.9800 |
C12—O6 | 1.422 (2) | C26—H26B | 0.9800 |
C12—H12 | 1.0000 | C26—H26C | 0.9800 |
C13—C18 | 1.385 (3) | C27—H27A | 0.9800 |
C13—C14 | 1.390 (3) | C27—H27B | 0.9800 |
C14—C15 | 1.385 (3) | C27—H27C | 0.9800 |
C14—H14 | 0.9500 | N1—O1 | 1.225 (2) |
C15—C16 | 1.383 (3) | N1—O2 | 1.228 (2) |
C15—H15 | 0.9500 | N2—O4 | 1.225 (3) |
C16—C17 | 1.378 (3) | N2—O3 | 1.231 (2) |
C16—N2 | 1.464 (3) | ||
C2—C1—C6 | 122.66 (18) | C17—C18—H18 | 119.4 |
C2—C1—N1 | 118.00 (18) | C13—C18—H18 | 119.4 |
C6—C1—N1 | 119.30 (17) | C21—C19—C20 | 109.59 (18) |
C1—C2—C3 | 118.68 (19) | C21—C19—Si1 | 113.24 (14) |
C1—C2—H2 | 120.7 | C20—C19—Si1 | 114.69 (14) |
C3—C2—H2 | 120.7 | C21—C19—H19 | 106.2 |
C2—C3—C4 | 120.39 (19) | C20—C19—H19 | 106.2 |
C2—C3—H3 | 119.8 | Si1—C19—H19 | 106.2 |
C4—C3—H3 | 119.8 | C19—C20—H20A | 109.5 |
C3—C4—C5 | 119.17 (18) | C19—C20—H20B | 109.5 |
C3—C4—C7 | 121.40 (17) | H20A—C20—H20B | 109.5 |
C5—C4—C7 | 119.42 (17) | C19—C20—H20C | 109.5 |
C6—C5—C4 | 120.91 (19) | H20A—C20—H20C | 109.5 |
C6—C5—H5 | 119.5 | H20B—C20—H20C | 109.5 |
C4—C5—H5 | 119.5 | C19—C21—H21A | 109.5 |
C1—C6—C5 | 118.18 (18) | C19—C21—H21B | 109.5 |
C1—C6—H6 | 120.9 | H21A—C21—H21B | 109.5 |
C5—C6—H6 | 120.9 | C19—C21—H21C | 109.5 |
O5—C7—C4 | 109.31 (15) | H21A—C21—H21C | 109.5 |
O5—C7—C8 | 104.29 (14) | H21B—C21—H21C | 109.5 |
C4—C7—C8 | 115.15 (16) | C23—C22—C24 | 110.17 (17) |
O5—C7—H7 | 109.3 | C23—C22—Si1 | 112.37 (14) |
C4—C7—H7 | 109.3 | C24—C22—Si1 | 117.49 (14) |
C8—C7—H7 | 109.3 | C23—C22—H22 | 105.2 |
C7—C8—C9 | 105.30 (15) | C24—C22—H22 | 105.2 |
C7—C8—H8A | 110.7 | Si1—C22—H22 | 105.2 |
C9—C8—H8A | 110.7 | C22—C23—H23A | 109.5 |
C7—C8—H8B | 110.7 | C22—C23—H23B | 109.5 |
C9—C8—H8B | 110.7 | H23A—C23—H23B | 109.5 |
H8A—C8—H8B | 108.8 | C22—C23—H23C | 109.5 |
C10—C9—C8 | 111.47 (15) | H23A—C23—H23C | 109.5 |
C10—C9—C12 | 101.98 (14) | H23B—C23—H23C | 109.5 |
C8—C9—C12 | 102.37 (14) | C22—C24—H24A | 109.5 |
C10—C9—Si1 | 111.93 (12) | C22—C24—H24B | 109.5 |
C8—C9—Si1 | 113.97 (12) | H24A—C24—H24B | 109.5 |
C12—C9—Si1 | 114.16 (12) | C22—C24—H24C | 109.5 |
C11—C10—C9 | 103.60 (15) | H24A—C24—H24C | 109.5 |
C11—C10—H10A | 111.0 | H24B—C24—H24C | 109.5 |
C9—C10—H10A | 111.0 | C26—C25—C27 | 108.82 (17) |
C11—C10—H10B | 111.0 | C26—C25—Si1 | 111.40 (14) |
C9—C10—H10B | 111.0 | C27—C25—Si1 | 117.54 (14) |
H10A—C10—H10B | 109.0 | C26—C25—H25 | 106.1 |
O6—C11—C13 | 110.03 (15) | C27—C25—H25 | 106.1 |
O6—C11—C10 | 103.17 (15) | Si1—C25—H25 | 106.1 |
C13—C11—C10 | 115.11 (16) | C25—C26—H26A | 109.5 |
O6—C11—H11 | 109.4 | C25—C26—H26B | 109.5 |
C13—C11—H11 | 109.4 | H26A—C26—H26B | 109.5 |
C10—C11—H11 | 109.4 | C25—C26—H26C | 109.5 |
O5—C12—O6 | 111.53 (14) | H26A—C26—H26C | 109.5 |
O5—C12—C9 | 108.20 (14) | H26B—C26—H26C | 109.5 |
O6—C12—C9 | 107.84 (14) | C25—C27—H27A | 109.5 |
O5—C12—H12 | 109.7 | C25—C27—H27B | 109.5 |
O6—C12—H12 | 109.7 | H27A—C27—H27B | 109.5 |
C9—C12—H12 | 109.7 | C25—C27—H27C | 109.5 |
C18—C13—C14 | 119.57 (18) | H27A—C27—H27C | 109.5 |
C18—C13—C11 | 118.54 (17) | H27B—C27—H27C | 109.5 |
C14—C13—C11 | 121.89 (18) | O1—N1—O2 | 123.39 (17) |
C15—C14—C13 | 120.10 (19) | O1—N1—C1 | 118.51 (16) |
C15—C14—H14 | 119.9 | O2—N1—C1 | 118.09 (17) |
C13—C14—H14 | 119.9 | O4—N2—O3 | 123.35 (18) |
C16—C15—C14 | 118.65 (19) | O4—N2—C16 | 118.79 (18) |
C16—C15—H15 | 120.7 | O3—N2—C16 | 117.86 (18) |
C14—C15—H15 | 120.7 | C12—O5—C7 | 108.71 (14) |
C17—C16—C15 | 122.51 (18) | C12—O6—C11 | 108.17 (13) |
C17—C16—N2 | 118.88 (18) | C22—Si1—C19 | 107.17 (9) |
C15—C16—N2 | 118.60 (18) | C22—Si1—C25 | 109.72 (9) |
C16—C17—C18 | 117.88 (18) | C19—Si1—C25 | 109.06 (9) |
C16—C17—H17 | 121.1 | C22—Si1—C9 | 111.98 (8) |
C18—C17—H17 | 121.1 | C19—Si1—C9 | 107.82 (8) |
C17—C18—C13 | 121.27 (18) | C25—Si1—C9 | 110.97 (8) |
Experimental details
Crystal data | |
Chemical formula | C27H36N2O6Si |
Mr | 512.67 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 120 |
a, b, c (Å) | 11.4829 (3), 14.5419 (3), 15.7595 (4) |
V (Å3) | 2631.57 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.2 × 0.15 × 0.1 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.974, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14158, 4610, 4150 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.081, 1.08 |
No. of reflections | 4610 |
No. of parameters | 326 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.19 |
Absolute structure | Flack (1983), 1974 Friedel pairs |
Absolute structure parameter | −0.04 (11) |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, DENZO, COLLECT and maXus (Mackay et al., 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CAMERON (Watkin, et al., 1993), WinGX (Farrugia, 1998).
The title compound, (I), was prepared as part of an ongoing study into the Lewis-acid-mediated additions of silylated methylenecyclopropanes to aldehydes. It is an example of an achiral molecule crystalizing in a chiral space group and the angle between the two least-squares planes of the nitrophenyl groups is 34.65 (9)°.