Dimethyl[N-(4-oxidopent-3-en-2-ylidene)valinato-κ3O,N,O′]silicon(IV), C12H21NO3Si, (II), crystallizes in the orthorhombic space group P212121. The chiral compound undergoes two sharp enantiotropic phase transitions upon cooling. The first transformation occurs at 163 K to yield a unit cell with one axis having double length. This intermediate-temperature form has the monoclinic space group P21. The second transition takes place at 142 K and converts the single crystal into the low-temperature form in the orthorhombic space group P212121. This transition proceeds under tripling of the a axis of the high-temperature form. Both phase transitions are fully reversible and correspond to order–disorder transitions of the isopropyl group of the valine unit in the ligand backbone. The phase transitions presented here raise questions, since they do not fit into the rules of group–subgroup relationships.
Supporting information
CCDC references: 1402014; 1402013; 1402012
For all compounds, data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) for II-HT; WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and SHELXLE (Hübschle et al., 2011) for II-IT, II-LT.
(II-HT) Dimethyl[
N-(4-oxidopent-3-en-2-ylidene)valinato-
κ3O,
N,
O']silicon(II)
top
Crystal data top
C12H21NO3Si | Dx = 1.204 Mg m−3 |
Mr = 255.39 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3236 reflections |
a = 7.7870 (3) Å | θ = 1.8–29.6° |
b = 8.1899 (2) Å | µ = 0.16 mm−1 |
c = 22.0975 (6) Å | T = 203 K |
V = 1409.26 (7) Å3 | Prism, colourless |
Z = 4 | 0.40 × 0.21 × 0.18 mm |
F(000) = 552 | |
Data collection top
Stoe IPDS 2 diffractometer | 3236 independent reflections |
Radiation source: fine-focus sealed tube | 2989 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.0 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
rotation method scans | h = −10→10 |
Absorption correction: integration (X-RED; Stoe & Cie, 2009) | k = 0→10 |
Tmin = 0.828, Tmax = 0.932 | l = 0→28 |
3236 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.8892P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.116 | (Δ/σ)max = 0.006 |
S = 1.06 | Δρmax = 0.64 e Å−3 |
3236 reflections | Δρmin = −0.56 e Å−3 |
208 parameters | Absolute structure: Flack x determined using 1174 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
84 restraints | Absolute structure parameter: −0.05 (5) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Si1 | 0.58338 (10) | 0.22608 (10) | 0.91073 (4) | 0.0306 (2) | |
O1 | 0.6953 (3) | 0.4214 (3) | 0.91240 (11) | 0.0347 (5) | |
O2 | 0.4560 (3) | 0.0420 (3) | 0.90229 (18) | 0.0626 (9) | |
N1 | 0.3970 (3) | 0.3260 (3) | 0.87524 (10) | 0.0258 (5) | |
C1 | 0.7458 (6) | 0.6906 (5) | 0.9480 (2) | 0.0616 (12) | |
H1A | 0.7947 | 0.6543 | 0.9860 | 0.092* | |
H1B | 0.6831 | 0.7915 | 0.9543 | 0.092* | |
H1C | 0.8371 | 0.7089 | 0.9189 | 0.092* | |
C2 | 0.6263 (5) | 0.5630 (4) | 0.92431 (14) | 0.0365 (7) | |
C3 | 0.4562 (4) | 0.5934 (4) | 0.91335 (17) | 0.0361 (7) | |
H3 | 0.4102 | 0.6946 | 0.9252 | 0.043* | |
C4 | 0.3481 (4) | 0.4797 (4) | 0.88523 (12) | 0.0280 (6) | |
C5 | 0.1742 (4) | 0.5392 (4) | 0.86595 (17) | 0.0400 (8) | |
H5A | 0.1613 | 0.5247 | 0.8226 | 0.060* | |
H5B | 0.1627 | 0.6541 | 0.8759 | 0.060* | |
H5C | 0.0860 | 0.4774 | 0.8869 | 0.060* | |
C6 | 0.2780 (4) | 0.2139 (4) | 0.84422 (13) | 0.0379 (7) | |
H6A | 0.1593 | 0.2365 | 0.8579 | 0.045* | 0.624 (8) |
H6B | 0.1591 | 0.2566 | 0.8438 | 0.045* | 0.376 (8) |
O3A | 0.2266 (8) | −0.0650 (6) | 0.8503 (4) | 0.071 (2) | 0.624 (8) |
C7A | 0.3290 (8) | 0.0418 (4) | 0.8636 (4) | 0.0481 (17) | 0.624 (8) |
C8A | 0.2896 (5) | 0.2403 (8) | 0.77477 (13) | 0.0399 (15) | 0.624 (8) |
H8A | 0.2775 | 0.3593 | 0.7681 | 0.048* | 0.624 (8) |
C9A | 0.1409 (9) | 0.1602 (13) | 0.7406 (3) | 0.070 (3) | 0.624 (8) |
H9A1 | 0.1536 | 0.1802 | 0.6976 | 0.105* | 0.624 (8) |
H9A2 | 0.0330 | 0.2060 | 0.7545 | 0.105* | 0.624 (8) |
H9A3 | 0.1417 | 0.0435 | 0.7481 | 0.105* | 0.624 (8) |
C10A | 0.4622 (7) | 0.1922 (10) | 0.7469 (3) | 0.059 (2) | 0.624 (8) |
H10A | 0.4809 | 0.0760 | 0.7525 | 0.089* | 0.624 (8) |
H10B | 0.5536 | 0.2526 | 0.7666 | 0.089* | 0.624 (8) |
H10C | 0.4614 | 0.2174 | 0.7040 | 0.089* | 0.624 (8) |
O3B | 0.1998 (10) | −0.0599 (8) | 0.8910 (5) | 0.055 (3) | 0.376 (8) |
C7B | 0.2932 (11) | 0.0573 (8) | 0.8819 (4) | 0.035 (2) | 0.376 (8) |
C8B | 0.3286 (12) | 0.1371 (11) | 0.7827 (3) | 0.047 (3) | 0.376 (8) |
H8B | 0.4430 | 0.0845 | 0.7845 | 0.056* | 0.376 (8) |
C9B | 0.193 (2) | 0.022 (2) | 0.7570 (8) | 0.092 (6) | 0.376 (8) |
H9B1 | 0.1824 | −0.0734 | 0.7829 | 0.138* | 0.376 (8) |
H9B2 | 0.2261 | −0.0126 | 0.7167 | 0.138* | 0.376 (8) |
H9B3 | 0.0829 | 0.0776 | 0.7551 | 0.138* | 0.376 (8) |
C10B | 0.333 (3) | 0.2945 (14) | 0.7454 (5) | 0.083 (5) | 0.376 (8) |
H10D | 0.3633 | 0.2691 | 0.7039 | 0.124* | 0.376 (8) |
H10E | 0.4175 | 0.3685 | 0.7624 | 0.124* | 0.376 (8) |
H10F | 0.2207 | 0.3458 | 0.7464 | 0.124* | 0.376 (8) |
C11 | 0.7670 (5) | 0.1392 (5) | 0.8671 (2) | 0.0524 (10) | |
H11A | 0.7264 | 0.0504 | 0.8418 | 0.079* | |
H11B | 0.8533 | 0.0986 | 0.8950 | 0.079* | |
H11C | 0.8169 | 0.2236 | 0.8418 | 0.079* | |
C12 | 0.5824 (5) | 0.2103 (6) | 0.99447 (17) | 0.0540 (10) | |
H12A | 0.4960 | 0.1319 | 1.0070 | 0.081* | |
H12B | 0.5562 | 0.3162 | 1.0118 | 0.081* | |
H12C | 0.6944 | 0.1746 | 1.0084 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0244 (4) | 0.0288 (4) | 0.0388 (4) | 0.0055 (3) | −0.0039 (3) | 0.0031 (3) |
O1 | 0.0287 (10) | 0.0320 (11) | 0.0432 (12) | 0.0013 (8) | −0.0051 (10) | 0.0020 (11) |
O2 | 0.0378 (13) | 0.0260 (11) | 0.124 (3) | 0.0043 (10) | −0.0245 (16) | 0.0003 (16) |
N1 | 0.0252 (11) | 0.0286 (11) | 0.0236 (10) | 0.0052 (10) | −0.0019 (9) | 0.0004 (9) |
C1 | 0.057 (2) | 0.042 (2) | 0.086 (3) | −0.0080 (19) | −0.014 (2) | −0.017 (2) |
C2 | 0.0432 (18) | 0.0309 (15) | 0.0353 (16) | 0.0003 (13) | −0.0040 (13) | −0.0002 (12) |
C3 | 0.0399 (16) | 0.0293 (14) | 0.0392 (16) | 0.0063 (12) | 0.0031 (14) | −0.0017 (14) |
C4 | 0.0308 (14) | 0.0308 (14) | 0.0224 (12) | 0.0067 (12) | 0.0018 (11) | 0.0059 (11) |
C5 | 0.0332 (17) | 0.0378 (17) | 0.0491 (19) | 0.0115 (14) | −0.0039 (15) | 0.0070 (15) |
C6 | 0.0240 (13) | 0.0481 (18) | 0.0415 (17) | 0.0004 (14) | −0.0034 (12) | −0.0136 (16) |
O3A | 0.064 (3) | 0.029 (2) | 0.120 (6) | −0.011 (2) | −0.029 (4) | −0.014 (3) |
C7A | 0.046 (2) | 0.046 (2) | 0.052 (2) | 0.0015 (13) | 0.0016 (13) | −0.0041 (13) |
C8A | 0.036 (3) | 0.053 (4) | 0.030 (3) | −0.010 (3) | −0.001 (2) | −0.012 (3) |
C9A | 0.061 (4) | 0.097 (7) | 0.052 (4) | −0.030 (4) | −0.016 (3) | −0.018 (4) |
C10A | 0.054 (4) | 0.084 (5) | 0.040 (3) | −0.004 (4) | 0.013 (3) | −0.020 (3) |
O3B | 0.054 (5) | 0.026 (3) | 0.085 (7) | 0.003 (3) | −0.017 (5) | −0.013 (4) |
C7B | 0.033 (3) | 0.033 (2) | 0.038 (3) | 0.0022 (13) | 0.0010 (13) | −0.0056 (13) |
C8B | 0.052 (6) | 0.046 (6) | 0.042 (5) | 0.005 (5) | 0.000 (4) | −0.007 (4) |
C9B | 0.099 (12) | 0.108 (13) | 0.068 (9) | −0.041 (10) | 0.002 (8) | −0.046 (9) |
C10B | 0.125 (13) | 0.079 (10) | 0.045 (7) | −0.004 (10) | −0.012 (8) | −0.026 (7) |
C11 | 0.0380 (19) | 0.050 (2) | 0.069 (3) | 0.0167 (17) | −0.0009 (18) | −0.013 (2) |
C12 | 0.0396 (18) | 0.078 (3) | 0.0448 (18) | 0.001 (2) | −0.0018 (16) | 0.0263 (19) |
Geometric parameters (Å, º) top
Si1—O2 | 1.814 (3) | O3A—C7A | 1.2190 (14) |
Si1—O1 | 1.822 (2) | C8A—C9A | 1.5299 (14) |
Si1—N1 | 1.841 (2) | C8A—C10A | 1.5299 (14) |
Si1—C12 | 1.855 (4) | C8A—H8A | 0.9900 |
Si1—C11 | 1.866 (4) | C9A—H9A1 | 0.9700 |
O1—C2 | 1.304 (4) | C9A—H9A2 | 0.9700 |
O2—C7A | 1.308 (6) | C9A—H9A3 | 0.9700 |
O2—C7B | 1.352 (8) | C10A—H10A | 0.9700 |
N1—C4 | 1.334 (4) | C10A—H10B | 0.9700 |
N1—C6 | 1.473 (4) | C10A—H10C | 0.9700 |
C1—C2 | 1.494 (5) | O3B—C7B | 1.2215 (14) |
C1—H1A | 0.9700 | C8B—C10B | 1.5294 (14) |
C1—H1B | 0.9700 | C8B—C9B | 1.5297 (14) |
C1—H1C | 0.9700 | C8B—H8B | 0.9900 |
C2—C3 | 1.370 (5) | C9B—H9B1 | 0.9700 |
C3—C4 | 1.401 (5) | C9B—H9B2 | 0.9700 |
C3—H3 | 0.9400 | C9B—H9B3 | 0.9700 |
C4—C5 | 1.502 (4) | C10B—H10D | 0.9700 |
C5—H5A | 0.9700 | C10B—H10E | 0.9700 |
C5—H5B | 0.9700 | C10B—H10F | 0.9700 |
C5—H5C | 0.9700 | C11—H11A | 0.9700 |
C6—C7A | 1.5260 (14) | C11—H11B | 0.9700 |
C6—C7B | 1.5335 (14) | C11—H11C | 0.9700 |
C6—C8B | 1.5494 (14) | C12—H12A | 0.9700 |
C6—C8A | 1.5524 (14) | C12—H12B | 0.9700 |
C6—H6A | 0.9900 | C12—H12C | 0.9700 |
C6—H6B | 0.9900 | | |
| | | |
O2—Si1—O1 | 173.29 (13) | C9A—C8A—C10A | 110.9 (5) |
O2—Si1—N1 | 83.95 (12) | C9A—C8A—C6 | 112.6 (4) |
O1—Si1—N1 | 89.74 (11) | C10A—C8A—C6 | 114.4 (4) |
O2—Si1—C12 | 92.4 (2) | C9A—C8A—H8A | 106.1 |
O1—Si1—C12 | 92.46 (17) | C10A—C8A—H8A | 106.1 |
N1—Si1—C12 | 116.90 (16) | C6—C8A—H8A | 106.1 |
O2—Si1—C11 | 92.81 (17) | C8A—C9A—H9A1 | 109.5 |
O1—Si1—C11 | 88.78 (16) | C8A—C9A—H9A2 | 109.5 |
N1—Si1—C11 | 123.60 (16) | H9A1—C9A—H9A2 | 109.5 |
C12—Si1—C11 | 119.5 (2) | C8A—C9A—H9A3 | 109.5 |
C2—O1—Si1 | 126.0 (2) | H9A1—C9A—H9A3 | 109.5 |
C7A—O2—Si1 | 118.8 (2) | H9A2—C9A—H9A3 | 109.5 |
C7B—O2—Si1 | 118.0 (3) | C8A—C10A—H10A | 109.5 |
C4—N1—C6 | 119.1 (2) | C8A—C10A—H10B | 109.5 |
C4—N1—Si1 | 125.0 (2) | H10A—C10A—H10B | 109.5 |
C6—N1—Si1 | 114.65 (18) | C8A—C10A—H10C | 109.5 |
C2—C1—H1A | 109.5 | H10A—C10A—H10C | 109.5 |
C2—C1—H1B | 109.5 | H10B—C10A—H10C | 109.5 |
H1A—C1—H1B | 109.5 | O3B—C7B—O2 | 115.5 (6) |
C2—C1—H1C | 109.5 | O3B—C7B—C6 | 134.6 (7) |
H1A—C1—H1C | 109.5 | O2—C7B—C6 | 109.3 (4) |
H1B—C1—H1C | 109.5 | C10B—C8B—C9B | 109.7 (12) |
O1—C2—C3 | 121.6 (3) | C10B—C8B—C6 | 97.8 (6) |
O1—C2—C1 | 115.9 (3) | C9B—C8B—C6 | 113.6 (8) |
C3—C2—C1 | 122.5 (3) | C10B—C8B—H8B | 111.7 |
C2—C3—C4 | 122.6 (3) | C9B—C8B—H8B | 111.7 |
C2—C3—H3 | 118.7 | C6—C8B—H8B | 111.7 |
C4—C3—H3 | 118.7 | C8B—C9B—H9B1 | 109.5 |
N1—C4—C3 | 122.0 (3) | C8B—C9B—H9B2 | 109.5 |
N1—C4—C5 | 121.1 (3) | H9B1—C9B—H9B2 | 109.5 |
C3—C4—C5 | 116.9 (3) | C8B—C9B—H9B3 | 109.5 |
C4—C5—H5A | 109.5 | H9B1—C9B—H9B3 | 109.5 |
C4—C5—H5B | 109.5 | H9B2—C9B—H9B3 | 109.5 |
H5A—C5—H5B | 109.5 | C8B—C10B—H10D | 109.5 |
C4—C5—H5C | 109.5 | C8B—C10B—H10E | 109.5 |
H5A—C5—H5C | 109.5 | H10D—C10B—H10E | 109.5 |
H5B—C5—H5C | 109.5 | C8B—C10B—H10F | 109.5 |
N1—C6—C7A | 106.3 (3) | H10D—C10B—H10F | 109.5 |
N1—C6—C7B | 102.7 (4) | H10E—C10B—H10F | 109.5 |
N1—C6—C8B | 120.1 (4) | Si1—C11—H11A | 109.5 |
C7B—C6—C8B | 96.7 (6) | Si1—C11—H11B | 109.5 |
N1—C6—C8A | 109.7 (3) | H11A—C11—H11B | 109.5 |
C7A—C6—C8A | 113.0 (4) | Si1—C11—H11C | 109.5 |
N1—C6—H6A | 109.2 | H11A—C11—H11C | 109.5 |
C7A—C6—H6A | 109.2 | H11B—C11—H11C | 109.5 |
C8A—C6—H6A | 109.2 | Si1—C12—H12A | 109.5 |
N1—C6—H6B | 111.9 | Si1—C12—H12B | 109.5 |
C7B—C6—H6B | 111.9 | H12A—C12—H12B | 109.5 |
C8B—C6—H6B | 111.9 | Si1—C12—H12C | 109.5 |
O3A—C7A—O2 | 130.8 (5) | H12A—C12—H12C | 109.5 |
O3A—C7A—C6 | 115.2 (4) | H12B—C12—H12C | 109.5 |
O2—C7A—C6 | 112.3 (3) | | |
| | | |
N1—Si1—O1—C2 | 38.8 (3) | Si1—N1—C6—C7A | 12.3 (4) |
C12—Si1—O1—C2 | −78.1 (3) | C4—N1—C6—C7B | −136.2 (5) |
C11—Si1—O1—C2 | 162.4 (3) | Si1—N1—C6—C7B | 31.6 (5) |
N1—Si1—O2—C7A | 19.1 (5) | C4—N1—C6—C8B | 118.2 (5) |
C12—Si1—O2—C7A | 135.9 (5) | Si1—N1—C6—C8B | −74.1 (5) |
C11—Si1—O2—C7A | −104.4 (5) | C4—N1—C6—C8A | 82.0 (4) |
N1—Si1—O2—C7B | −5.8 (6) | Si1—N1—C6—C8A | −110.3 (3) |
C12—Si1—O2—C7B | 111.0 (6) | Si1—O2—C7A—O3A | −179.7 (8) |
C11—Si1—O2—C7B | −129.3 (6) | Si1—O2—C7A—C6 | −15.9 (8) |
O2—Si1—N1—C4 | 150.1 (3) | N1—C6—C7A—O3A | 168.3 (7) |
O1—Si1—N1—C4 | −32.2 (2) | C8A—C6—C7A—O3A | −71.3 (8) |
C12—Si1—N1—C4 | 60.5 (3) | N1—C6—C7A—O2 | 1.8 (7) |
C11—Si1—N1—C4 | −120.5 (3) | C8A—C6—C7A—O2 | 122.2 (6) |
O2—Si1—N1—C6 | −16.8 (2) | N1—C6—C8A—C9A | −165.9 (5) |
O1—Si1—N1—C6 | 160.9 (2) | C7A—C6—C8A—C9A | 75.6 (6) |
C12—Si1—N1—C6 | −106.5 (2) | N1—C6—C8A—C10A | 66.3 (6) |
C11—Si1—N1—C6 | 72.6 (3) | C7A—C6—C8A—C10A | −52.1 (6) |
Si1—O1—C2—C3 | −26.9 (5) | Si1—O2—C7B—O3B | −162.4 (8) |
Si1—O1—C2—C1 | 155.6 (3) | Si1—O2—C7B—C6 | 25.3 (9) |
O1—C2—C3—C4 | −4.3 (5) | N1—C6—C7B—O3B | 155.5 (12) |
C1—C2—C3—C4 | 173.0 (4) | C8B—C6—C7B—O3B | −81.5 (13) |
C6—N1—C4—C3 | −178.7 (3) | N1—C6—C7B—O2 | −34.3 (8) |
Si1—N1—C4—C3 | 15.0 (4) | C8B—C6—C7B—O2 | 88.7 (8) |
C6—N1—C4—C5 | 0.6 (4) | N1—C6—C8B—C10B | −65.4 (10) |
Si1—N1—C4—C5 | −165.8 (2) | C7B—C6—C8B—C10B | −174.4 (9) |
C2—C3—C4—N1 | 10.0 (5) | N1—C6—C8B—C9B | 179.0 (10) |
C2—C3—C4—C5 | −169.3 (3) | C7B—C6—C8B—C9B | 70.1 (11) |
C4—N1—C6—C7A | −155.5 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O3Ai | 0.97 | 2.42 | 3.285 (6) | 148 |
C5—H5B···O3Bi | 0.97 | 2.38 | 3.335 (8) | 167 |
C3—H3···O3Bi | 0.94 | 2.70 | 3.506 (9) | 144 |
Symmetry code: (i) x, y+1, z. |
(II-IT) Dimethyl[
N-(4-oxidopent-3-en-2-ylidene)valinato-
κ3O,
N,
O']silicon(II)
top
Crystal data top
C12H21NO3Si | F(000) = 1104 |
Mr = 255.39 | Dx = 1.219 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 15.3969 (3) Å | Cell parameters from 79178 reflections |
b = 8.1763 (1) Å | θ = 1.6–28.1° |
c = 22.1067 (5) Å | µ = 0.17 mm−1 |
β = 90.010 (2)° | T = 153 K |
V = 2783.01 (9) Å3 | Prism, colourless |
Z = 8 | 0.40 × 0.21 × 0.18 mm |
Data collection top
Stoe IPDS 2 diffractometer | 12488 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 11928 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.077 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
rotation method scans | h = −19→19 |
Absorption correction: integration (X-RED; Stoe & Cie, 2009) | k = −10→10 |
Tmin = 0.794, Tmax = 0.994 | l = −28→28 |
79178 measured reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.7358P]
where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max < 0.001 |
wR(F2) = 0.107 | Δρmax = 0.23 e Å−3 |
S = 1.10 | Δρmin = −0.22 e Å−3 |
12488 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
715 parameters | Extinction coefficient: 0.037 (2) |
161 restraints | Absolute structure: Flack x determined using 5183 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons & Flack, 2004) |
Hydrogen site location: inferred from neighbouring sites | Absolute structure parameter: −0.01 (4) |
Special details top
Experimental. loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k
_exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 30 1 2 0.1324 30 - 2
5 0.0545 - 30 0 0 0.0926 - 30 2 - 7 0.0635 - 30 2 5 0.3299 |
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. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Si1A | 0.29310 (13) | 0.53543 (18) | 0.15930 (8) | 0.0282 (4) | |
O1A | 0.3498 (3) | 0.7304 (5) | 0.1604 (2) | 0.0303 (9) | |
O2A | 0.2280 (3) | 0.3492 (6) | 0.1539 (3) | 0.0498 (15) | |
O3A | 0.1068 (10) | 0.2479 (16) | 0.1026 (9) | 0.094 (5) | 0.5 |
O3B | 0.0968 (7) | 0.2432 (13) | 0.1390 (5) | 0.049 (2) | 0.5 |
N1A | 0.1978 (4) | 0.6338 (7) | 0.1244 (2) | 0.0287 (11) | |
C1A | 0.3743 (5) | 1.0007 (9) | 0.1950 (3) | 0.0403 (15) | |
H1A | 0.4067 | 0.9581 | 0.2297 | 0.060* | |
H1B | 0.3399 | 1.0955 | 0.2076 | 0.060* | |
H1C | 0.4152 | 1.0337 | 0.1632 | 0.060* | |
C2A | 0.3161 (5) | 0.8726 (8) | 0.1714 (3) | 0.0314 (13) | |
C3A | 0.2279 (5) | 0.9036 (8) | 0.1621 (3) | 0.0326 (13) | |
H3A | 0.2037 | 1.0049 | 0.1746 | 0.039* | |
C4A | 0.1749 (4) | 0.7859 (7) | 0.1342 (3) | 0.0283 (12) | |
C5A | 0.0833 (4) | 0.8453 (8) | 0.1169 (3) | 0.0381 (14) | |
H5A | 0.0707 | 0.8140 | 0.0750 | 0.057* | |
H5B | 0.0805 | 0.9646 | 0.1207 | 0.057* | |
H5C | 0.0404 | 0.7952 | 0.1439 | 0.057* | |
C6A | 0.1381 (4) | 0.5159 (8) | 0.0949 (3) | 0.0384 (14) | |
H6A | 0.0783 | 0.5509 | 0.1069 | 0.046* | 0.5 |
H6B | 0.0761 | 0.5517 | 0.0979 | 0.046* | 0.5 |
C7A | 0.1531 (4) | 0.3570 (8) | 0.1263 (4) | 0.061 (3) | |
C8A | 0.1451 (8) | 0.552 (2) | 0.0224 (6) | 0.053 (3) | 0.5 |
H8A | 0.1356 | 0.6725 | 0.0170 | 0.064* | 0.5 |
C9A | 0.0714 (10) | 0.468 (2) | −0.0096 (8) | 0.075 (5) | 0.5 |
H9A | 0.0734 | 0.4941 | −0.0528 | 0.113* | 0.5 |
H9B | 0.0161 | 0.5047 | 0.0075 | 0.113* | 0.5 |
H9C | 0.0769 | 0.3492 | −0.0042 | 0.113* | 0.5 |
C10A | 0.2306 (8) | 0.515 (2) | −0.0048 (6) | 0.067 (4) | 0.5 |
H10A | 0.2357 | 0.3966 | −0.0110 | 0.100* | 0.5 |
H10B | 0.2768 | 0.5520 | 0.0223 | 0.100* | 0.5 |
H10C | 0.2358 | 0.5711 | −0.0438 | 0.100* | 0.5 |
C8B | 0.1611 (8) | 0.4564 (15) | 0.0304 (5) | 0.042 (2) | 0.5 |
H8B | 0.2225 | 0.4167 | 0.0303 | 0.050* | 0.5 |
C9B | 0.1035 (11) | 0.324 (2) | 0.0055 (7) | 0.068 (4) | 0.5 |
H9D | 0.0436 | 0.3634 | 0.0031 | 0.102* | 0.5 |
H9E | 0.1059 | 0.2279 | 0.0321 | 0.102* | 0.5 |
H9F | 0.1236 | 0.2928 | −0.0350 | 0.102* | 0.5 |
C10B | 0.1557 (12) | 0.6054 (19) | −0.0065 (8) | 0.064 (4) | 0.5 |
H10D | 0.1830 | 0.5858 | −0.0459 | 0.097* | 0.5 |
H10E | 0.1858 | 0.6949 | 0.0142 | 0.097* | 0.5 |
H10F | 0.0946 | 0.6350 | −0.0125 | 0.097* | 0.5 |
C11A | 0.3842 (5) | 0.4444 (9) | 0.1138 (3) | 0.0401 (15) | |
H11A | 0.4209 | 0.5323 | 0.0978 | 0.060* | |
H11B | 0.3600 | 0.3809 | 0.0802 | 0.060* | |
H11C | 0.4190 | 0.3727 | 0.1397 | 0.060* | |
C12A | 0.2946 (5) | 0.5204 (10) | 0.2436 (3) | 0.0380 (15) | |
H12A | 0.2355 | 0.5350 | 0.2593 | 0.057* | |
H12B | 0.3325 | 0.6056 | 0.2602 | 0.057* | |
H12C | 0.3165 | 0.4126 | 0.2556 | 0.057* | |
Si1B | 0.54069 (12) | 0.60317 (15) | 0.33490 (7) | 0.0225 (3) | |
O1B | 0.5956 (3) | 0.4047 (5) | 0.3410 (2) | 0.0272 (9) | |
O2B | 0.4755 (2) | 0.7904 (4) | 0.33406 (17) | 0.0251 (7) | |
O3C | 0.3450 (2) | 0.8940 (4) | 0.35678 (17) | 0.0258 (7) | |
N1B | 0.4456 (3) | 0.5158 (5) | 0.3744 (2) | 0.0204 (9) | |
C1B | 0.6160 (4) | 0.1333 (9) | 0.3069 (4) | 0.0442 (17) | |
H1D | 0.6326 | 0.1569 | 0.2650 | 0.066* | |
H1E | 0.5860 | 0.0277 | 0.3086 | 0.066* | |
H1F | 0.6681 | 0.1292 | 0.3322 | 0.066* | |
C2B | 0.5570 (4) | 0.2642 (7) | 0.3293 (3) | 0.0256 (11) | |
C3 | 0.4711 (4) | 0.2429 (6) | 0.3409 (3) | 0.0266 (11) | |
H3B | 0.4460 | 0.1408 | 0.3302 | 0.032* | |
C4B | 0.4167 (4) | 0.3602 (6) | 0.3675 (2) | 0.0219 (10) | |
C5B | 0.3298 (3) | 0.3080 (6) | 0.3880 (3) | 0.0272 (10) | |
H5D | 0.3259 | 0.3192 | 0.4320 | 0.041* | |
H5E | 0.3204 | 0.1935 | 0.3767 | 0.041* | |
H5F | 0.2855 | 0.3766 | 0.3688 | 0.041* | |
C6B | 0.3893 (3) | 0.6418 (5) | 0.4021 (2) | 0.0195 (8) | |
H6C | 0.3276 | 0.6041 | 0.4015 | 0.023* | |
C7B | 0.3994 (3) | 0.7901 (5) | 0.36137 (18) | 0.0199 (8) | |
C8C | 0.4174 (3) | 0.6775 (5) | 0.46794 (19) | 0.0218 (8) | |
H8C | 0.4794 | 0.7138 | 0.4670 | 0.026* | |
C9C | 0.4118 (4) | 0.5271 (6) | 0.5099 (2) | 0.0340 (11) | |
H9G | 0.4323 | 0.5568 | 0.5504 | 0.051* | |
H9H | 0.4480 | 0.4390 | 0.4936 | 0.051* | |
H9I | 0.3513 | 0.4900 | 0.5123 | 0.051* | |
C10C | 0.3641 (4) | 0.8164 (7) | 0.4937 (2) | 0.0407 (12) | |
H10G | 0.3715 | 0.9139 | 0.4684 | 0.061* | |
H10H | 0.3837 | 0.8404 | 0.5349 | 0.061* | |
H10I | 0.3027 | 0.7851 | 0.4944 | 0.061* | |
C11B | 0.6299 (4) | 0.6972 (7) | 0.3788 (3) | 0.0343 (13) | |
H11D | 0.6309 | 0.6505 | 0.4196 | 0.052* | |
H11E | 0.6206 | 0.8156 | 0.3813 | 0.052* | |
H11F | 0.6854 | 0.6754 | 0.3586 | 0.052* | |
C12B | 0.5433 (5) | 0.5986 (10) | 0.2502 (3) | 0.0373 (14) | |
H12D | 0.6028 | 0.6178 | 0.2362 | 0.056* | |
H12E | 0.5051 | 0.6841 | 0.2342 | 0.056* | |
H12F | 0.5234 | 0.4915 | 0.2359 | 0.056* | |
Si1C | 0.79262 (13) | 0.54265 (18) | 0.16386 (9) | 0.0288 (4) | |
O1C | 0.8493 (3) | 0.7373 (5) | 0.1637 (2) | 0.0306 (9) | |
O2C | 0.7270 (3) | 0.3590 (6) | 0.1594 (3) | 0.0539 (16) | |
O3D | 0.6115 (10) | 0.2573 (16) | 0.1028 (8) | 0.091 (5) | 0.5 |
O3E | 0.5997 (6) | 0.2459 (11) | 0.1412 (6) | 0.049 (2) | 0.5 |
N1C | 0.6989 (4) | 0.6385 (6) | 0.1256 (2) | 0.0266 (10) | |
C1C | 0.8726 (5) | 1.0073 (10) | 0.1970 (4) | 0.0516 (19) | |
H25G | 0.9032 | 0.9662 | 0.2328 | 0.077* | |
H25H | 0.8381 | 1.1035 | 0.2081 | 0.077* | |
H25I | 0.9150 | 1.0376 | 0.1659 | 0.077* | |
C2C | 0.8147 (5) | 0.8788 (8) | 0.1733 (3) | 0.0353 (14) | |
C3C | 0.7269 (5) | 0.9093 (7) | 0.1623 (3) | 0.0318 (12) | |
H3C | 0.7020 | 1.0106 | 0.1741 | 0.038* | |
C4C | 0.6754 (4) | 0.7906 (8) | 0.1336 (3) | 0.0292 (12) | |
C5C | 0.5854 (4) | 0.8503 (8) | 0.1131 (3) | 0.0407 (14) | |
H5G | 0.5744 | 0.8132 | 0.0716 | 0.061* | |
H5H | 0.5836 | 0.9701 | 0.1144 | 0.061* | |
H5I | 0.5408 | 0.8058 | 0.1400 | 0.061* | |
C6C | 0.6408 (4) | 0.5200 (8) | 0.0954 (3) | 0.0402 (15) | |
H6D | 0.5807 | 0.5552 | 0.1066 | 0.048* | 0.5 |
H6E | 0.5786 | 0.5556 | 0.0952 | 0.048* | 0.5 |
C7C | 0.6549 (5) | 0.3623 (8) | 0.1287 (4) | 0.064 (3) | |
C8D | 0.6492 (8) | 0.559 (2) | 0.0219 (6) | 0.050 (3) | 0.5 |
H8D | 0.6405 | 0.6789 | 0.0159 | 0.060* | 0.5 |
C9D | 0.7344 (10) | 0.517 (3) | −0.0007 (8) | 0.080 (5) | 0.5 |
H9J | 0.7419 | 0.3981 | 0.0003 | 0.120* | 0.5 |
H9K | 0.7788 | 0.5688 | 0.0246 | 0.120* | 0.5 |
H9L | 0.7403 | 0.5560 | −0.0425 | 0.120* | 0.5 |
C10D | 0.5756 (10) | 0.471 (3) | −0.0095 (8) | 0.081 (5) | 0.5 |
H10J | 0.5732 | 0.5046 | −0.0520 | 0.122* | 0.5 |
H10K | 0.5206 | 0.4978 | 0.0104 | 0.122* | 0.5 |
H10L | 0.5854 | 0.3524 | −0.0073 | 0.122* | 0.5 |
C8E | 0.6713 (8) | 0.4511 (16) | 0.0330 (5) | 0.046 (3) | 0.5 |
H8E | 0.7326 | 0.4121 | 0.0370 | 0.055* | 0.5 |
C9E | 0.6700 (12) | 0.593 (2) | −0.0066 (7) | 0.064 (4) | 0.5 |
H9M | 0.6915 | 0.5623 | −0.0467 | 0.096* | 0.5 |
H9N | 0.7073 | 0.6790 | 0.0103 | 0.096* | 0.5 |
H9O | 0.6104 | 0.6343 | −0.0101 | 0.096* | 0.5 |
C10E | 0.6168 (12) | 0.313 (2) | 0.0090 (7) | 0.074 (5) | 0.5 |
H10M | 0.5617 | 0.3092 | 0.0312 | 0.111* | 0.5 |
H10N | 0.6479 | 0.2098 | 0.0142 | 0.111* | 0.5 |
H10O | 0.6051 | 0.3313 | −0.0341 | 0.111* | 0.5 |
C11C | 0.8846 (5) | 0.4485 (9) | 0.1203 (4) | 0.0439 (16) | |
H11G | 0.9210 | 0.3841 | 0.1477 | 0.066* | |
H11H | 0.9196 | 0.5351 | 0.1017 | 0.066* | |
H11I | 0.8611 | 0.3772 | 0.0886 | 0.066* | |
C12C | 0.7917 (6) | 0.5348 (12) | 0.2480 (3) | 0.0489 (19) | |
H12G | 0.7334 | 0.5613 | 0.2628 | 0.073* | |
H12H | 0.8334 | 0.6143 | 0.2641 | 0.073* | |
H12I | 0.8078 | 0.4247 | 0.2615 | 0.073* | |
Si1D | 0.04508 (13) | 0.57856 (15) | 0.34271 (8) | 0.0272 (4) | |
O1D | 0.1026 (3) | 0.3822 (5) | 0.3371 (2) | 0.0314 (10) | |
O2D | −0.0203 (3) | 0.7629 (5) | 0.3565 (2) | 0.0334 (9) | |
O3F | −0.1373 (2) | 0.8690 (5) | 0.3985 (2) | 0.0403 (9) | |
N1D | −0.0486 (3) | 0.4709 (5) | 0.3767 (2) | 0.0212 (9) | |
C1D | 0.1312 (5) | 0.1152 (10) | 0.2991 (4) | 0.0503 (18) | |
H1J | 0.1408 | 0.1341 | 0.2558 | 0.075* | |
H1K | 0.1072 | 0.0053 | 0.3051 | 0.075* | |
H1L | 0.1864 | 0.1248 | 0.3208 | 0.075* | |
C2D | 0.0679 (5) | 0.2408 (7) | 0.3231 (3) | 0.0303 (13) | |
C3D | −0.0158 (4) | 0.2064 (7) | 0.3343 (3) | 0.0292 (11) | |
H3D | −0.0375 | 0.1030 | 0.3218 | 0.035* | |
C4D | −0.0735 (4) | 0.3155 (6) | 0.3636 (2) | 0.0241 (11) | |
C5D | −0.1598 (4) | 0.2553 (6) | 0.3815 (3) | 0.0292 (11) | |
H5J | −0.1641 | 0.2537 | 0.4257 | 0.044* | |
H5K | −0.1682 | 0.1444 | 0.3657 | 0.044* | |
H5L | −0.2046 | 0.3277 | 0.3649 | 0.044* | |
C6D | −0.1103 (3) | 0.5789 (5) | 0.4086 (2) | 0.0220 (9) | |
H6F | −0.1707 | 0.5504 | 0.3958 | 0.026* | |
C7D | −0.0900 (3) | 0.7538 (6) | 0.3882 (2) | 0.0303 (10) | |
C8F | −0.1036 (3) | 0.5639 (6) | 0.47760 (18) | 0.0223 (8) | |
H8F | −0.1111 | 0.4455 | 0.4876 | 0.027* | |
C9F | −0.1764 (3) | 0.6563 (7) | 0.5101 (3) | 0.0396 (12) | |
H9P | −0.1698 | 0.6432 | 0.5539 | 0.059* | |
H9Q | −0.2327 | 0.6123 | 0.4974 | 0.059* | |
H9R | −0.1733 | 0.7727 | 0.4997 | 0.059* | |
C10F | −0.0142 (3) | 0.6153 (8) | 0.5020 (2) | 0.0350 (11) | |
H10P | −0.0043 | 0.7312 | 0.4931 | 0.053* | |
H10Q | 0.0311 | 0.5494 | 0.4826 | 0.053* | |
H10R | −0.0123 | 0.5980 | 0.5458 | 0.053* | |
C11D | 0.1396 (4) | 0.6602 (7) | 0.3858 (4) | 0.0399 (15) | |
H11J | 0.1251 | 0.7682 | 0.4022 | 0.060* | |
H11K | 0.1898 | 0.6697 | 0.3589 | 0.060* | |
H11L | 0.1536 | 0.5857 | 0.4192 | 0.060* | |
C12D | 0.0422 (5) | 0.6059 (11) | 0.2594 (3) | 0.0446 (16) | |
H12J | 0.0211 | 0.5053 | 0.2403 | 0.067* | |
H12K | 0.1008 | 0.6304 | 0.2446 | 0.067* | |
H12L | 0.0032 | 0.6966 | 0.2492 | 0.067* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1A | 0.0260 (7) | 0.0283 (7) | 0.0304 (9) | 0.0046 (5) | −0.0033 (6) | −0.0021 (6) |
O1A | 0.029 (2) | 0.0287 (19) | 0.033 (2) | 0.0056 (16) | 0.0025 (17) | 0.0007 (16) |
O2A | 0.036 (2) | 0.031 (2) | 0.082 (4) | 0.0057 (17) | −0.018 (2) | −0.008 (2) |
O3A | 0.081 (9) | 0.043 (6) | 0.159 (13) | 0.001 (6) | −0.051 (11) | −0.025 (9) |
O3B | 0.044 (5) | 0.034 (4) | 0.069 (6) | −0.001 (4) | −0.014 (5) | −0.014 (5) |
N1A | 0.030 (2) | 0.033 (2) | 0.0226 (19) | 0.0015 (18) | −0.0046 (17) | 0.0010 (17) |
C1A | 0.046 (3) | 0.033 (3) | 0.042 (3) | 0.000 (2) | 0.002 (3) | −0.004 (2) |
C2A | 0.036 (3) | 0.031 (3) | 0.027 (2) | 0.005 (2) | 0.002 (2) | 0.002 (2) |
C3A | 0.048 (3) | 0.025 (2) | 0.025 (2) | 0.003 (2) | 0.004 (2) | −0.0017 (19) |
C4A | 0.027 (2) | 0.034 (3) | 0.024 (2) | 0.0088 (19) | 0.0023 (18) | 0.003 (2) |
C5A | 0.038 (3) | 0.039 (3) | 0.037 (3) | 0.013 (2) | 0.000 (2) | 0.004 (2) |
C6A | 0.026 (2) | 0.052 (3) | 0.037 (3) | 0.001 (2) | −0.004 (2) | −0.012 (3) |
C7A | 0.036 (3) | 0.035 (3) | 0.111 (7) | 0.006 (2) | −0.015 (3) | −0.028 (4) |
C8A | 0.047 (6) | 0.055 (8) | 0.057 (7) | −0.011 (6) | −0.007 (6) | −0.019 (7) |
C9A | 0.066 (8) | 0.094 (12) | 0.066 (9) | −0.001 (8) | −0.014 (7) | −0.027 (8) |
C10A | 0.064 (8) | 0.096 (11) | 0.040 (6) | −0.006 (8) | 0.007 (6) | −0.003 (7) |
C8B | 0.045 (5) | 0.040 (6) | 0.040 (5) | 0.003 (5) | 0.006 (4) | −0.007 (5) |
C9B | 0.086 (10) | 0.070 (9) | 0.048 (7) | −0.017 (8) | −0.007 (7) | −0.005 (6) |
C10B | 0.084 (10) | 0.057 (9) | 0.052 (8) | −0.002 (8) | 0.001 (8) | −0.017 (7) |
C11A | 0.032 (3) | 0.047 (3) | 0.041 (3) | 0.015 (2) | 0.003 (2) | −0.012 (2) |
C12A | 0.037 (3) | 0.049 (4) | 0.028 (3) | −0.004 (3) | −0.001 (2) | 0.016 (3) |
Si1B | 0.0231 (7) | 0.0197 (6) | 0.0246 (6) | −0.0036 (5) | 0.0011 (6) | 0.0051 (5) |
O1B | 0.025 (2) | 0.0229 (18) | 0.033 (2) | −0.0004 (15) | 0.0057 (16) | −0.0009 (14) |
O2B | 0.0257 (16) | 0.0175 (15) | 0.0323 (15) | −0.0004 (12) | 0.0032 (12) | 0.0118 (12) |
O3C | 0.0260 (15) | 0.0180 (14) | 0.0334 (17) | 0.0043 (12) | −0.0020 (13) | 0.0105 (13) |
N1B | 0.0207 (19) | 0.0147 (17) | 0.0257 (19) | −0.0018 (15) | −0.0012 (15) | −0.0012 (14) |
C1B | 0.037 (3) | 0.031 (3) | 0.065 (4) | 0.002 (3) | 0.022 (3) | −0.001 (3) |
C2B | 0.030 (3) | 0.020 (2) | 0.027 (2) | 0.0019 (19) | 0.0027 (19) | −0.0017 (19) |
C3 | 0.028 (2) | 0.020 (2) | 0.032 (2) | −0.0051 (18) | 0.0050 (19) | −0.0042 (18) |
C4B | 0.025 (2) | 0.017 (2) | 0.023 (2) | 0.0015 (18) | −0.0015 (17) | 0.0040 (16) |
C5B | 0.029 (2) | 0.0155 (19) | 0.037 (2) | −0.0044 (17) | 0.004 (2) | −0.0020 (18) |
C6B | 0.0203 (19) | 0.0118 (17) | 0.0262 (19) | 0.0029 (14) | −0.0004 (15) | −0.0006 (14) |
C7B | 0.027 (2) | 0.0173 (18) | 0.0157 (15) | −0.0003 (16) | −0.0021 (14) | 0.0048 (14) |
C8C | 0.029 (2) | 0.0168 (18) | 0.0198 (18) | −0.0004 (16) | −0.0017 (16) | −0.0030 (15) |
C9C | 0.052 (3) | 0.031 (2) | 0.018 (2) | 0.004 (2) | −0.006 (2) | 0.0062 (18) |
C10C | 0.057 (3) | 0.035 (3) | 0.030 (2) | 0.013 (2) | 0.007 (2) | −0.014 (2) |
C11B | 0.033 (3) | 0.024 (2) | 0.047 (3) | −0.002 (2) | −0.004 (2) | 0.001 (2) |
C12B | 0.031 (3) | 0.050 (3) | 0.031 (3) | −0.001 (3) | 0.003 (2) | 0.001 (2) |
Si1C | 0.0252 (7) | 0.0287 (7) | 0.0325 (9) | 0.0028 (6) | −0.0010 (6) | −0.0010 (7) |
O1C | 0.026 (2) | 0.0309 (19) | 0.035 (2) | 0.0010 (16) | −0.0002 (18) | 0.0008 (16) |
O2C | 0.038 (2) | 0.032 (2) | 0.091 (4) | 0.0064 (18) | −0.014 (2) | −0.008 (2) |
O3D | 0.080 (8) | 0.050 (6) | 0.143 (12) | −0.006 (6) | −0.017 (9) | −0.017 (9) |
O3E | 0.038 (4) | 0.026 (4) | 0.082 (6) | −0.005 (3) | −0.009 (5) | −0.011 (5) |
N1C | 0.027 (2) | 0.034 (2) | 0.0189 (18) | −0.0060 (18) | −0.0003 (15) | 0.0015 (16) |
C1C | 0.045 (4) | 0.039 (3) | 0.071 (5) | 0.003 (3) | −0.006 (3) | −0.022 (3) |
C2C | 0.030 (3) | 0.034 (3) | 0.042 (3) | 0.000 (2) | −0.001 (2) | −0.001 (2) |
C3C | 0.036 (3) | 0.024 (2) | 0.035 (3) | −0.002 (2) | 0.005 (2) | 0.000 (2) |
C4C | 0.023 (2) | 0.037 (3) | 0.027 (2) | 0.003 (2) | 0.0024 (19) | 0.009 (2) |
C5C | 0.032 (3) | 0.045 (3) | 0.046 (3) | 0.008 (2) | −0.004 (2) | 0.009 (3) |
C6C | 0.031 (3) | 0.053 (3) | 0.037 (3) | −0.006 (2) | 0.001 (2) | −0.014 (3) |
C7C | 0.039 (3) | 0.033 (3) | 0.121 (8) | 0.006 (3) | −0.008 (4) | −0.024 (4) |
C8D | 0.046 (6) | 0.058 (7) | 0.048 (6) | −0.023 (6) | −0.008 (5) | −0.014 (6) |
C9D | 0.077 (9) | 0.111 (13) | 0.051 (7) | −0.007 (10) | −0.006 (7) | −0.020 (8) |
C10D | 0.068 (8) | 0.119 (14) | 0.057 (8) | −0.032 (9) | −0.010 (7) | −0.032 (9) |
C8E | 0.043 (6) | 0.052 (6) | 0.042 (5) | −0.007 (5) | −0.007 (4) | −0.007 (5) |
C9E | 0.084 (10) | 0.068 (9) | 0.040 (6) | 0.014 (8) | −0.001 (7) | 0.000 (7) |
C10E | 0.096 (11) | 0.067 (9) | 0.058 (8) | −0.033 (8) | 0.015 (8) | −0.017 (7) |
C11C | 0.035 (3) | 0.048 (3) | 0.049 (3) | 0.013 (3) | −0.003 (3) | −0.012 (3) |
C12C | 0.039 (4) | 0.073 (5) | 0.034 (3) | −0.004 (3) | −0.003 (3) | 0.027 (3) |
Si1D | 0.0257 (7) | 0.0241 (7) | 0.0317 (7) | −0.0018 (6) | 0.0021 (6) | 0.0056 (5) |
O1D | 0.029 (2) | 0.0267 (19) | 0.038 (2) | 0.0038 (17) | 0.0046 (18) | −0.0031 (17) |
O2D | 0.0292 (18) | 0.0201 (16) | 0.051 (2) | 0.0010 (14) | 0.0075 (15) | 0.0120 (15) |
O3F | 0.0348 (18) | 0.0183 (15) | 0.068 (3) | 0.0098 (13) | 0.0104 (18) | 0.0120 (18) |
N1D | 0.024 (2) | 0.0138 (17) | 0.0260 (19) | −0.0036 (15) | −0.0034 (16) | 0.0002 (14) |
C1D | 0.048 (4) | 0.045 (3) | 0.058 (4) | 0.020 (3) | 0.014 (3) | −0.017 (3) |
C2D | 0.044 (3) | 0.025 (2) | 0.022 (2) | 0.005 (2) | 0.001 (2) | −0.0051 (18) |
C3D | 0.034 (3) | 0.025 (2) | 0.028 (2) | −0.003 (2) | −0.001 (2) | −0.0046 (19) |
C4D | 0.038 (3) | 0.0134 (19) | 0.0213 (19) | −0.0044 (17) | −0.0086 (19) | 0.0003 (15) |
C5D | 0.029 (2) | 0.019 (2) | 0.039 (3) | −0.0006 (17) | −0.005 (2) | 0.0022 (18) |
C6D | 0.019 (2) | 0.0125 (16) | 0.034 (2) | 0.0003 (14) | 0.0013 (16) | 0.0036 (15) |
C7D | 0.027 (2) | 0.022 (2) | 0.042 (2) | 0.0033 (17) | −0.0011 (18) | 0.0095 (18) |
C8F | 0.0237 (19) | 0.025 (2) | 0.0180 (17) | −0.0004 (17) | −0.0007 (15) | −0.0029 (16) |
C9F | 0.036 (2) | 0.047 (3) | 0.036 (3) | 0.011 (2) | 0.011 (2) | −0.010 (2) |
C10F | 0.026 (2) | 0.051 (3) | 0.028 (2) | −0.003 (2) | −0.0077 (17) | −0.015 (2) |
C11D | 0.032 (3) | 0.025 (2) | 0.062 (4) | 0.001 (2) | 0.006 (3) | −0.007 (2) |
C12D | 0.034 (3) | 0.058 (4) | 0.042 (3) | −0.007 (3) | 0.006 (3) | 0.013 (3) |
Geometric parameters (Å, º) top
Si1A—O1A | 1.818 (5) | Si1C—O2C | 1.813 (5) |
Si1A—O2A | 1.827 (5) | Si1C—O1C | 1.815 (5) |
Si1A—N1A | 1.842 (6) | Si1C—N1C | 1.847 (6) |
Si1A—C12A | 1.868 (7) | Si1C—C12C | 1.862 (8) |
Si1A—C11A | 1.879 (7) | Si1C—C11C | 1.878 (7) |
O1A—C2A | 1.297 (8) | O1C—C2C | 1.291 (9) |
O2A—C7A | 1.305 (8) | O2C—C7C | 1.301 (9) |
O3A—C7A | 1.257 (13) | O3D—C7C | 1.230 (13) |
O3B—C7A | 1.302 (13) | O3E—C7C | 1.306 (11) |
N1A—C4A | 1.310 (8) | N1C—C4C | 1.307 (8) |
N1A—C6A | 1.484 (8) | N1C—C6C | 1.478 (8) |
C1A—C2A | 1.474 (9) | C1C—C2C | 1.474 (9) |
C1A—H1A | 0.9800 | C1C—H25G | 0.9800 |
C1A—H1B | 0.9800 | C1C—H25H | 0.9800 |
C1A—H1C | 0.9800 | C1C—H25I | 0.9800 |
C2A—C3A | 1.395 (10) | C2C—C3C | 1.396 (10) |
C3A—C4A | 1.405 (9) | C3C—C4C | 1.405 (8) |
C3A—H3A | 0.9500 | C3C—H3C | 0.9500 |
C4A—C5A | 1.540 (9) | C4C—C5C | 1.537 (8) |
C5A—H5A | 0.9800 | C5C—H5G | 0.9800 |
C5A—H5B | 0.9800 | C5C—H5H | 0.9800 |
C5A—H5C | 0.9800 | C5C—H5I | 0.9800 |
C6A—C7A | 1.492 (10) | C6C—C7C | 1.502 (10) |
C6A—C8B | 1.547 (12) | C6C—C8E | 1.562 (13) |
C6A—C8A | 1.634 (16) | C6C—C8D | 1.660 (15) |
C6A—H6A | 1.0000 | C6C—H6D | 1.0000 |
C6A—H6B | 1.0000 | C6C—H6E | 1.0000 |
C8A—C10A | 1.479 (15) | C8D—C9D | 1.446 (17) |
C8A—C9A | 1.505 (15) | C8D—C10D | 1.511 (15) |
C8A—H8A | 1.0000 | C8D—H8D | 1.0000 |
C9A—H9A | 0.9800 | C9D—H9J | 0.9800 |
C9A—H9B | 0.9800 | C9D—H9K | 0.9800 |
C9A—H9C | 0.9800 | C9D—H9L | 0.9800 |
C10A—H10A | 0.9800 | C10D—H10J | 0.9800 |
C10A—H10B | 0.9800 | C10D—H10K | 0.9800 |
C10A—H10C | 0.9800 | C10D—H10L | 0.9800 |
C8B—C10B | 1.468 (16) | C8E—C9E | 1.456 (17) |
C8B—C9B | 1.506 (15) | C8E—C10E | 1.501 (15) |
C8B—H8B | 1.0000 | C8E—H8E | 1.0000 |
C9B—H9D | 0.9800 | C9E—H9M | 0.9800 |
C9B—H9E | 0.9800 | C9E—H9N | 0.9800 |
C9B—H9F | 0.9800 | C9E—H9O | 0.9800 |
C10B—H10D | 0.9800 | C10E—H10M | 0.9800 |
C10B—H10E | 0.9800 | C10E—H10N | 0.9800 |
C10B—H10F | 0.9800 | C10E—H10O | 0.9800 |
C11A—H11A | 0.9800 | C11C—H11G | 0.9800 |
C11A—H11B | 0.9800 | C11C—H11H | 0.9800 |
C11A—H11C | 0.9800 | C11C—H11I | 0.9800 |
C12A—H12A | 0.9800 | C12C—H12G | 0.9800 |
C12A—H12B | 0.9800 | C12C—H12H | 0.9800 |
C12A—H12C | 0.9800 | C12C—H12I | 0.9800 |
Si1B—O2B | 1.830 (4) | Si1D—O2D | 1.838 (4) |
Si1B—O1B | 1.835 (4) | Si1D—O1D | 1.838 (5) |
Si1B—C11B | 1.848 (7) | Si1D—N1D | 1.849 (5) |
Si1B—N1B | 1.849 (5) | Si1D—C12D | 1.857 (8) |
Si1B—C12B | 1.873 (7) | Si1D—C11D | 1.863 (7) |
O1B—C2B | 1.319 (8) | O1D—C2D | 1.311 (8) |
O2B—C7B | 1.318 (6) | O2D—C7D | 1.283 (7) |
O3C—C7B | 1.198 (5) | O3F—C7D | 1.212 (6) |
N1B—C4B | 1.356 (6) | N1D—C4D | 1.358 (6) |
N1B—C6B | 1.479 (6) | N1D—C6D | 1.476 (6) |
C1B—C2B | 1.489 (8) | C1D—C2D | 1.511 (8) |
C1B—H1D | 0.9800 | C1D—H1J | 0.9800 |
C1B—H1E | 0.9800 | C1D—H1K | 0.9800 |
C1B—H1F | 0.9800 | C1D—H1L | 0.9800 |
C2B—C3 | 1.359 (9) | C2D—C3D | 1.342 (9) |
C3—C4B | 1.403 (7) | C3D—C4D | 1.416 (8) |
C3—H3B | 0.9500 | C3D—H3D | 0.9500 |
C4B—C5B | 1.474 (7) | C4D—C5D | 1.472 (8) |
C5B—H5D | 0.9800 | C5D—H5J | 0.9800 |
C5B—H5E | 0.9800 | C5D—H5K | 0.9800 |
C5B—H5F | 0.9800 | C5D—H5L | 0.9800 |
C6B—C7B | 1.518 (6) | C6D—C7D | 1.532 (6) |
C6B—C8C | 1.547 (6) | C6D—C8F | 1.533 (6) |
C6B—H6C | 1.0000 | C6D—H6F | 1.0000 |
C8C—C10C | 1.512 (6) | C8F—C9F | 1.530 (6) |
C8C—C9C | 1.543 (6) | C8F—C10F | 1.537 (5) |
C8C—H8C | 1.0000 | C8F—H8F | 1.0000 |
C9C—H9G | 0.9800 | C9F—H9P | 0.9800 |
C9C—H9H | 0.9800 | C9F—H9Q | 0.9800 |
C9C—H9I | 0.9800 | C9F—H9R | 0.9800 |
C10C—H10G | 0.9800 | C10F—H10P | 0.9800 |
C10C—H10H | 0.9800 | C10F—H10Q | 0.9800 |
C10C—H10I | 0.9800 | C10F—H10R | 0.9800 |
C11B—H11D | 0.9800 | C11D—H11J | 0.9800 |
C11B—H11E | 0.9800 | C11D—H11K | 0.9800 |
C11B—H11F | 0.9800 | C11D—H11L | 0.9800 |
C12B—H12D | 0.9800 | C12D—H12J | 0.9800 |
C12B—H12E | 0.9800 | C12D—H12K | 0.9800 |
C12B—H12F | 0.9800 | C12D—H12L | 0.9800 |
| | | |
O1A—Si1A—O2A | 174.5 (2) | O2C—Si1C—O1C | 173.9 (2) |
O1A—Si1A—N1A | 90.3 (2) | O2C—Si1C—N1C | 83.7 (2) |
O2A—Si1A—N1A | 84.3 (2) | O1C—Si1C—N1C | 90.2 (2) |
O1A—Si1A—C12A | 92.2 (3) | O2C—Si1C—C12C | 91.2 (4) |
O2A—Si1A—C12A | 91.0 (3) | O1C—Si1C—C12C | 92.0 (4) |
N1A—Si1A—C12A | 117.1 (3) | N1C—Si1C—C12C | 117.8 (3) |
O1A—Si1A—C11A | 89.8 (3) | O2C—Si1C—C11C | 93.0 (3) |
O2A—Si1A—C11A | 92.5 (3) | O1C—Si1C—C11C | 89.8 (3) |
N1A—Si1A—C11A | 122.9 (3) | N1C—Si1C—C11C | 121.9 (3) |
C12A—Si1A—C11A | 119.9 (4) | C12C—Si1C—C11C | 120.3 (4) |
C2A—O1A—Si1A | 126.6 (5) | C2C—O1C—Si1C | 126.0 (5) |
C7A—O2A—Si1A | 118.3 (5) | C7C—O2C—Si1C | 119.1 (5) |
C4A—N1A—C6A | 121.4 (6) | C4C—N1C—C6C | 121.1 (6) |
C4A—N1A—Si1A | 124.1 (5) | C4C—N1C—Si1C | 123.9 (4) |
C6A—N1A—Si1A | 113.2 (4) | C6C—N1C—Si1C | 113.7 (4) |
C2A—C1A—H1A | 109.5 | C2C—C1C—H25G | 109.5 |
C2A—C1A—H1B | 109.5 | C2C—C1C—H25H | 109.5 |
H1A—C1A—H1B | 109.5 | H25G—C1C—H25H | 109.5 |
C2A—C1A—H1C | 109.5 | C2C—C1C—H25I | 109.5 |
H1A—C1A—H1C | 109.5 | H25G—C1C—H25I | 109.5 |
H1B—C1A—H1C | 109.5 | H25H—C1C—H25I | 109.5 |
O1A—C2A—C3A | 121.7 (6) | O1C—C2C—C3C | 122.1 (6) |
O1A—C2A—C1A | 117.3 (6) | O1C—C2C—C1C | 116.6 (6) |
C3A—C2A—C1A | 121.0 (6) | C3C—C2C—C1C | 121.3 (6) |
C2A—C3A—C4A | 120.4 (6) | C2C—C3C—C4C | 120.2 (6) |
C2A—C3A—H3A | 119.8 | C2C—C3C—H3C | 119.9 |
C4A—C3A—H3A | 119.8 | C4C—C3C—H3C | 119.9 |
N1A—C4A—C3A | 124.4 (6) | N1C—C4C—C3C | 124.2 (6) |
N1A—C4A—C5A | 120.4 (6) | N1C—C4C—C5C | 120.8 (6) |
C3A—C4A—C5A | 115.2 (5) | C3C—C4C—C5C | 115.0 (6) |
C4A—C5A—H5A | 109.5 | C4C—C5C—H5G | 109.5 |
C4A—C5A—H5B | 109.5 | C4C—C5C—H5H | 109.5 |
H5A—C5A—H5B | 109.5 | H5G—C5C—H5H | 109.5 |
C4A—C5A—H5C | 109.5 | C4C—C5C—H5I | 109.5 |
H5A—C5A—H5C | 109.5 | H5G—C5C—H5I | 109.5 |
H5B—C5A—H5C | 109.5 | H5H—C5C—H5I | 109.5 |
N1A—C6A—C7A | 105.4 (5) | N1C—C6C—C7C | 104.7 (5) |
N1A—C6A—C8B | 117.9 (6) | N1C—C6C—C8E | 116.9 (6) |
C7A—C6A—C8B | 96.9 (7) | C7C—C6C—C8E | 94.5 (7) |
N1A—C6A—C8A | 105.8 (6) | N1C—C6C—C8D | 105.7 (6) |
C7A—C6A—C8A | 127.3 (8) | C7C—C6C—C8D | 129.3 (8) |
N1A—C6A—H6A | 105.6 | N1C—C6C—H6D | 105.1 |
C7A—C6A—H6A | 105.6 | C7C—C6C—H6D | 105.1 |
C8A—C6A—H6A | 105.6 | C8D—C6C—H6D | 105.1 |
N1A—C6A—H6B | 111.8 | N1C—C6C—H6E | 113.0 |
C7A—C6A—H6B | 111.8 | C7C—C6C—H6E | 113.0 |
C8B—C6A—H6B | 111.8 | C8E—C6C—H6E | 113.0 |
O3A—C7A—O2A | 131.4 (9) | O3D—C7C—O2C | 133.8 (10) |
O3B—C7A—O2A | 117.0 (8) | O2C—C7C—O3E | 115.5 (8) |
O3A—C7A—C6A | 109.6 (10) | O3D—C7C—C6C | 107.0 (10) |
O3B—C7A—C6A | 128.2 (7) | O2C—C7C—C6C | 113.4 (6) |
O2A—C7A—C6A | 113.4 (6) | O3E—C7C—C6C | 129.4 (7) |
C10A—C8A—C9A | 112.6 (12) | C9D—C8D—C10D | 114.1 (12) |
C10A—C8A—C6A | 114.8 (12) | C9D—C8D—C6C | 111.4 (12) |
C9A—C8A—C6A | 109.1 (12) | C10D—C8D—C6C | 107.5 (11) |
C10A—C8A—H8A | 106.6 | C9D—C8D—H8D | 107.9 |
C9A—C8A—H8A | 106.6 | C10D—C8D—H8D | 107.9 |
C6A—C8A—H8A | 106.6 | C6C—C8D—H8D | 107.9 |
C8A—C9A—H9A | 109.5 | C8D—C9D—H9J | 109.5 |
C8A—C9A—H9B | 109.5 | C8D—C9D—H9K | 109.5 |
H9A—C9A—H9B | 109.5 | H9J—C9D—H9K | 109.5 |
C8A—C9A—H9C | 109.5 | C8D—C9D—H9L | 109.5 |
H9A—C9A—H9C | 109.5 | H9J—C9D—H9L | 109.5 |
H9B—C9A—H9C | 109.5 | H9K—C9D—H9L | 109.5 |
C8A—C10A—H10A | 109.5 | C8D—C10D—H10J | 109.5 |
C8A—C10A—H10B | 109.5 | C8D—C10D—H10K | 109.5 |
H10A—C10A—H10B | 109.5 | H10J—C10D—H10K | 109.5 |
C8A—C10A—H10C | 109.5 | C8D—C10D—H10L | 109.5 |
H10A—C10A—H10C | 109.5 | H10J—C10D—H10L | 109.5 |
H10B—C10A—H10C | 109.5 | H10K—C10D—H10L | 109.5 |
C10B—C8B—C9B | 111.2 (12) | C9E—C8E—C10E | 112.3 (12) |
C10B—C8B—C6A | 103.8 (10) | C9E—C8E—C6C | 103.8 (10) |
C9B—C8B—C6A | 115.4 (10) | C10E—C8E—C6C | 114.5 (10) |
C10B—C8B—H8B | 108.7 | C9E—C8E—H8E | 108.7 |
C9B—C8B—H8B | 108.7 | C10E—C8E—H8E | 108.7 |
C6A—C8B—H8B | 108.7 | C6C—C8E—H8E | 108.7 |
C8B—C9B—H9D | 109.5 | C8E—C9E—H9M | 109.5 |
C8B—C9B—H9E | 109.5 | C8E—C9E—H9N | 109.5 |
H9D—C9B—H9E | 109.5 | H9M—C9E—H9N | 109.5 |
C8B—C9B—H9F | 109.5 | C8E—C9E—H9O | 109.5 |
H9D—C9B—H9F | 109.5 | H9M—C9E—H9O | 109.5 |
H9E—C9B—H9F | 109.5 | H9N—C9E—H9O | 109.5 |
C8B—C10B—H10D | 109.5 | C8E—C10E—H10M | 109.5 |
C8B—C10B—H10E | 109.5 | C8E—C10E—H10N | 109.5 |
H10D—C10B—H10E | 109.5 | H10M—C10E—H10N | 109.5 |
C8B—C10B—H10F | 109.5 | C8E—C10E—H10O | 109.5 |
H10D—C10B—H10F | 109.5 | H10M—C10E—H10O | 109.5 |
H10E—C10B—H10F | 109.5 | H10N—C10E—H10O | 109.5 |
Si1A—C11A—H11A | 109.5 | Si1C—C11C—H11G | 109.5 |
Si1A—C11A—H11B | 109.5 | Si1C—C11C—H11H | 109.5 |
H11A—C11A—H11B | 109.5 | H11G—C11C—H11H | 109.5 |
Si1A—C11A—H11C | 109.5 | Si1C—C11C—H11I | 109.5 |
H11A—C11A—H11C | 109.5 | H11G—C11C—H11I | 109.5 |
H11B—C11A—H11C | 109.5 | H11H—C11C—H11I | 109.5 |
Si1A—C12A—H12A | 109.5 | Si1C—C12C—H12G | 109.5 |
Si1A—C12A—H12B | 109.5 | Si1C—C12C—H12H | 109.5 |
H12A—C12A—H12B | 109.5 | H12G—C12C—H12H | 109.5 |
Si1A—C12A—H12C | 109.5 | Si1C—C12C—H12I | 109.5 |
H12A—C12A—H12C | 109.5 | H12G—C12C—H12I | 109.5 |
H12B—C12A—H12C | 109.5 | H12H—C12C—H12I | 109.5 |
O2B—Si1B—O1B | 173.2 (2) | O2D—Si1D—O1D | 172.5 (2) |
O2B—Si1B—C11B | 93.7 (2) | O2D—Si1D—N1D | 84.01 (19) |
O1B—Si1B—C11B | 89.2 (2) | O1D—Si1D—N1D | 89.3 (2) |
O2B—Si1B—N1B | 83.91 (19) | O2D—Si1D—C12D | 93.1 (3) |
O1B—Si1B—N1B | 89.4 (2) | O1D—Si1D—C12D | 92.9 (3) |
C11B—Si1B—N1B | 120.1 (3) | N1D—Si1D—C12D | 116.2 (3) |
O2B—Si1B—C12B | 91.1 (3) | O2D—Si1D—C11D | 92.8 (2) |
O1B—Si1B—C12B | 92.6 (3) | O1D—Si1D—C11D | 88.3 (3) |
C11B—Si1B—C12B | 121.1 (3) | N1D—Si1D—C11D | 124.9 (3) |
N1B—Si1B—C12B | 118.8 (3) | C12D—Si1D—C11D | 118.9 (4) |
C2B—O1B—Si1B | 123.2 (4) | C2D—O1D—Si1D | 126.1 (5) |
C7B—O2B—Si1B | 118.8 (3) | C7D—O2D—Si1D | 120.1 (3) |
C4B—N1B—C6B | 120.5 (5) | C4D—N1D—C6D | 118.7 (5) |
C4B—N1B—Si1B | 124.7 (4) | C4D—N1D—Si1D | 125.4 (4) |
C6B—N1B—Si1B | 112.9 (3) | C6D—N1D—Si1D | 114.3 (3) |
C2B—C1B—H1D | 109.5 | C2D—C1D—H1J | 109.5 |
C2B—C1B—H1E | 109.5 | C2D—C1D—H1K | 109.5 |
H1D—C1B—H1E | 109.5 | H1J—C1D—H1K | 109.5 |
C2B—C1B—H1F | 109.5 | C2D—C1D—H1L | 109.5 |
H1D—C1B—H1F | 109.5 | H1J—C1D—H1L | 109.5 |
H1E—C1B—H1F | 109.5 | H1K—C1D—H1L | 109.5 |
O1B—C2B—C3 | 120.9 (5) | O1D—C2D—C3D | 122.2 (5) |
O1B—C2B—C1B | 114.6 (6) | O1D—C2D—C1D | 114.8 (6) |
C3—C2B—C1B | 124.4 (5) | C3D—C2D—C1D | 122.8 (6) |
C2B—C3—C4B | 125.0 (5) | C2D—C3D—C4D | 123.7 (5) |
C2B—C3—H3B | 117.5 | C2D—C3D—H3D | 118.1 |
C4B—C3—H3B | 117.5 | C4D—C3D—H3D | 118.1 |
N1B—C4B—C3 | 119.5 (5) | N1D—C4D—C3D | 120.6 (6) |
N1B—C4B—C5B | 122.3 (5) | N1D—C4D—C5D | 120.7 (5) |
C3—C4B—C5B | 118.2 (5) | C3D—C4D—C5D | 118.6 (5) |
C4B—C5B—H5D | 109.5 | C4D—C5D—H5J | 109.5 |
C4B—C5B—H5E | 109.5 | C4D—C5D—H5K | 109.5 |
H5D—C5B—H5E | 109.5 | H5J—C5D—H5K | 109.5 |
C4B—C5B—H5F | 109.5 | C4D—C5D—H5L | 109.5 |
H5D—C5B—H5F | 109.5 | H5J—C5D—H5L | 109.5 |
H5E—C5B—H5F | 109.5 | H5K—C5D—H5L | 109.5 |
N1B—C6B—C7B | 104.6 (4) | N1D—C6D—C7D | 106.6 (4) |
N1B—C6B—C8C | 110.9 (4) | N1D—C6D—C8F | 112.7 (4) |
C7B—C6B—C8C | 112.2 (3) | C7D—C6D—C8F | 110.7 (4) |
N1B—C6B—H6C | 109.7 | N1D—C6D—H6F | 108.9 |
C7B—C6B—H6C | 109.7 | C7D—C6D—H6F | 108.9 |
C8C—C6B—H6C | 109.7 | C8F—C6D—H6F | 108.9 |
O3C—C7B—O2B | 125.6 (4) | O3F—C7D—O2D | 124.1 (5) |
O3C—C7B—C6B | 123.0 (4) | O3F—C7D—C6D | 123.2 (5) |
O2B—C7B—C6B | 111.3 (4) | O2D—C7D—C6D | 112.6 (4) |
C10C—C8C—C9C | 110.0 (4) | C9F—C8F—C6D | 112.2 (4) |
C10C—C8C—C6B | 110.1 (4) | C9F—C8F—C10F | 110.9 (4) |
C9C—C8C—C6B | 113.5 (4) | C6D—C8F—C10F | 112.7 (4) |
C10C—C8C—H8C | 107.6 | C9F—C8F—H8F | 106.9 |
C9C—C8C—H8C | 107.6 | C6D—C8F—H8F | 106.9 |
C6B—C8C—H8C | 107.6 | C10F—C8F—H8F | 106.9 |
C8C—C9C—H9G | 109.5 | C8F—C9F—H9P | 109.5 |
C8C—C9C—H9H | 109.5 | C8F—C9F—H9Q | 109.5 |
H9G—C9C—H9H | 109.5 | H9P—C9F—H9Q | 109.5 |
C8C—C9C—H9I | 109.5 | C8F—C9F—H9R | 109.5 |
H9G—C9C—H9I | 109.5 | H9P—C9F—H9R | 109.5 |
H9H—C9C—H9I | 109.5 | H9Q—C9F—H9R | 109.5 |
C8C—C10C—H10G | 109.5 | C8F—C10F—H10P | 109.5 |
C8C—C10C—H10H | 109.5 | C8F—C10F—H10Q | 109.5 |
H10G—C10C—H10H | 109.5 | H10P—C10F—H10Q | 109.5 |
C8C—C10C—H10I | 109.5 | C8F—C10F—H10R | 109.5 |
H10G—C10C—H10I | 109.5 | H10P—C10F—H10R | 109.5 |
H10H—C10C—H10I | 109.5 | H10Q—C10F—H10R | 109.5 |
Si1B—C11B—H11D | 109.5 | Si1D—C11D—H11J | 109.5 |
Si1B—C11B—H11E | 109.5 | Si1D—C11D—H11K | 109.5 |
H11D—C11B—H11E | 109.5 | H11J—C11D—H11K | 109.5 |
Si1B—C11B—H11F | 109.5 | Si1D—C11D—H11L | 109.5 |
H11D—C11B—H11F | 109.5 | H11J—C11D—H11L | 109.5 |
H11E—C11B—H11F | 109.5 | H11K—C11D—H11L | 109.5 |
Si1B—C12B—H12D | 109.5 | Si1D—C12D—H12J | 109.5 |
Si1B—C12B—H12E | 109.5 | Si1D—C12D—H12K | 109.5 |
H12D—C12B—H12E | 109.5 | H12J—C12D—H12K | 109.5 |
Si1B—C12B—H12F | 109.5 | Si1D—C12D—H12L | 109.5 |
H12D—C12B—H12F | 109.5 | H12J—C12D—H12L | 109.5 |
H12E—C12B—H12F | 109.5 | H12K—C12D—H12L | 109.5 |
| | | |
N1A—Si1A—O1A—C2A | 37.7 (6) | N1C—Si1C—O1C—C2C | 39.0 (6) |
C12A—Si1A—O1A—C2A | −79.5 (6) | C12C—Si1C—O1C—C2C | −78.8 (6) |
C11A—Si1A—O1A—C2A | 160.6 (6) | C11C—Si1C—O1C—C2C | 160.8 (6) |
N1A—Si1A—O2A—C7A | 5.2 (6) | N1C—Si1C—O2C—C7C | 7.5 (6) |
C12A—Si1A—O2A—C7A | 122.3 (6) | C12C—Si1C—O2C—C7C | 125.3 (6) |
C11A—Si1A—O2A—C7A | −117.6 (6) | C11C—Si1C—O2C—C7C | −114.2 (6) |
O1A—Si1A—N1A—C4A | −31.3 (5) | O2C—Si1C—N1C—C4C | 148.3 (5) |
O2A—Si1A—N1A—C4A | 149.5 (5) | O1C—Si1C—N1C—C4C | −32.2 (5) |
C12A—Si1A—N1A—C4A | 61.3 (6) | C12C—Si1C—N1C—C4C | 60.2 (6) |
C11A—Si1A—N1A—C4A | −121.2 (5) | C11C—Si1C—N1C—C4C | −122.0 (5) |
O1A—Si1A—N1A—C6A | 161.5 (4) | O2C—Si1C—N1C—C6C | −18.9 (4) |
O2A—Si1A—N1A—C6A | −17.7 (4) | O1C—Si1C—N1C—C6C | 160.6 (4) |
C12A—Si1A—N1A—C6A | −105.9 (5) | C12C—Si1C—N1C—C6C | −107.0 (5) |
C11A—Si1A—N1A—C6A | 71.6 (5) | C11C—Si1C—N1C—C6C | 70.7 (5) |
Si1A—O1A—C2A—C3A | −24.4 (9) | Si1C—O1C—C2C—C3C | −25.3 (10) |
Si1A—O1A—C2A—C1A | 155.1 (5) | Si1C—O1C—C2C—C1C | 154.3 (6) |
O1A—C2A—C3A—C4A | −6.8 (10) | O1C—C2C—C3C—C4C | −7.3 (11) |
C1A—C2A—C3A—C4A | 173.8 (6) | C1C—C2C—C3C—C4C | 173.1 (7) |
C6A—N1A—C4A—C3A | 179.7 (6) | C6C—N1C—C4C—C3C | 179.6 (6) |
Si1A—N1A—C4A—C3A | 13.5 (9) | Si1C—N1C—C4C—C3C | 13.3 (8) |
C6A—N1A—C4A—C5A | 2.0 (8) | C6C—N1C—C4C—C5C | 1.4 (8) |
Si1A—N1A—C4A—C5A | −164.2 (5) | Si1C—N1C—C4C—C5C | −164.9 (5) |
C2A—C3A—C4A—N1A | 11.9 (10) | C2C—C3C—C4C—N1C | 13.0 (10) |
C2A—C3A—C4A—C5A | −170.2 (6) | C2C—C3C—C4C—C5C | −168.7 (6) |
C4A—N1A—C6A—C7A | −142.6 (6) | C4C—N1C—C6C—C7C | −142.8 (6) |
Si1A—N1A—C6A—C7A | 25.0 (6) | Si1C—N1C—C6C—C7C | 24.8 (6) |
C4A—N1A—C6A—C8B | 110.8 (8) | C4C—N1C—C6C—C8E | 114.2 (8) |
Si1A—N1A—C6A—C8B | −81.6 (8) | Si1C—N1C—C6C—C8E | −78.2 (8) |
C4A—N1A—C6A—C8A | 80.5 (9) | C4C—N1C—C6C—C8D | 78.3 (8) |
Si1A—N1A—C6A—C8A | −111.9 (7) | Si1C—N1C—C6C—C8D | −114.1 (7) |
Si1A—O2A—C7A—O3A | 159.1 (15) | Si1C—O2C—C7C—O3D | 154.7 (15) |
Si1A—O2A—C7A—O3B | −158.8 (7) | Si1C—O2C—C7C—O3E | −161.1 (7) |
Si1A—O2A—C7A—C6A | 8.7 (8) | Si1C—O2C—C7C—C6C | 5.7 (9) |
N1A—C6A—C7A—O3A | −177.8 (11) | N1C—C6C—C7C—O3D | −176.2 (10) |
C8B—C6A—C7A—O3A | −56.4 (12) | C8E—C6C—C7C—O3D | −56.8 (11) |
C8A—C6A—C7A—O3A | −53.5 (14) | C8D—C6C—C7C—O3D | −51.1 (13) |
N1A—C6A—C7A—O3B | 144.8 (9) | N1C—C6C—C7C—O2C | −19.0 (8) |
C8B—C6A—C7A—O3B | −93.7 (11) | C8E—C6C—C7C—O2C | 100.4 (8) |
C8A—C6A—C7A—O3B | −90.9 (12) | C8D—C6C—C7C—O2C | 106.0 (9) |
N1A—C6A—C7A—O2A | −21.0 (8) | N1C—C6C—C7C—O3E | 145.5 (9) |
C8B—C6A—C7A—O2A | 100.4 (8) | C8E—C6C—C7C—O3E | −95.2 (11) |
C8A—C6A—C7A—O2A | 103.3 (9) | C8D—C6C—C7C—O3E | −89.5 (12) |
N1A—C6A—C8A—C10A | 66.2 (14) | N1C—C6C—C8D—C9D | 67.9 (14) |
C7A—C6A—C8A—C10A | −57.9 (15) | C7C—C6C—C8D—C9D | −56.7 (15) |
C8B—C6A—C8A—C10A | −52.3 (15) | C8E—C6C—C8D—C9D | −46.9 (13) |
N1A—C6A—C8A—C9A | −166.3 (11) | N1C—C6C—C8D—C10D | −166.4 (11) |
C7A—C6A—C8A—C9A | 69.5 (14) | C7C—C6C—C8D—C10D | 68.9 (14) |
C8B—C6A—C8A—C9A | 75.1 (16) | C8E—C6C—C8D—C10D | 78.8 (14) |
N1A—C6A—C8B—C10B | −64.4 (12) | N1C—C6C—C8E—C9E | −66.1 (12) |
C7A—C6A—C8B—C10B | −175.8 (10) | C7C—C6C—C8E—C9E | −175.0 (10) |
C8A—C6A—C8B—C10B | 8.6 (12) | C8D—C6C—C8E—C9E | 12.6 (10) |
N1A—C6A—C8B—C9B | 173.7 (10) | N1C—C6C—C8E—C10E | 171.2 (11) |
C7A—C6A—C8B—C9B | 62.2 (12) | C7C—C6C—C8E—C10E | 62.3 (12) |
C8A—C6A—C8B—C9B | −113.3 (18) | C8D—C6C—C8E—C10E | −110.1 (16) |
C11B—Si1B—O1B—C2B | 164.7 (5) | N1D—Si1D—O1D—C2D | 38.2 (5) |
N1B—Si1B—O1B—C2B | 44.6 (5) | C12D—Si1D—O1D—C2D | −78.0 (6) |
C12B—Si1B—O1B—C2B | −74.2 (5) | C11D—Si1D—O1D—C2D | 163.2 (5) |
C11B—Si1B—O2B—C7B | −116.5 (4) | N1D—Si1D—O2D—C7D | 9.5 (5) |
N1B—Si1B—O2B—C7B | 3.4 (3) | C12D—Si1D—O2D—C7D | 125.5 (5) |
C12B—Si1B—O2B—C7B | 122.3 (4) | C11D—Si1D—O2D—C7D | −115.3 (5) |
O2B—Si1B—N1B—C4B | 144.3 (4) | O2D—Si1D—N1D—C4D | 150.9 (5) |
O1B—Si1B—N1B—C4B | −36.2 (4) | O1D—Si1D—N1D—C4D | −32.4 (5) |
C11B—Si1B—N1B—C4B | −124.9 (4) | C12D—Si1D—N1D—C4D | 60.4 (6) |
C12B—Si1B—N1B—C4B | 56.5 (5) | C11D—Si1D—N1D—C4D | −119.9 (5) |
O2B—Si1B—N1B—C6B | −20.4 (3) | O2D—Si1D—N1D—C6D | −14.1 (4) |
O1B—Si1B—N1B—C6B | 159.2 (4) | O1D—Si1D—N1D—C6D | 162.6 (4) |
C11B—Si1B—N1B—C6B | 70.4 (4) | C12D—Si1D—N1D—C6D | −104.6 (4) |
C12B—Si1B—N1B—C6B | −108.2 (4) | C11D—Si1D—N1D—C6D | 75.1 (4) |
Si1B—O1B—C2B—C3 | −32.8 (8) | Si1D—O1D—C2D—C3D | −27.5 (9) |
Si1B—O1B—C2B—C1B | 150.9 (5) | Si1D—O1D—C2D—C1D | 158.1 (5) |
O1B—C2B—C3—C4B | −2.4 (10) | O1D—C2D—C3D—C4D | −2.0 (10) |
C1B—C2B—C3—C4B | 173.5 (6) | C1D—C2D—C3D—C4D | 171.9 (6) |
C6B—N1B—C4B—C3 | 179.7 (5) | C6D—N1D—C4D—C3D | −178.5 (5) |
Si1B—N1B—C4B—C3 | 16.2 (7) | Si1D—N1D—C4D—C3D | 17.1 (7) |
C6B—N1B—C4B—C5B | −1.2 (7) | C6D—N1D—C4D—C5D | −0.7 (7) |
Si1B—N1B—C4B—C5B | −164.8 (4) | Si1D—N1D—C4D—C5D | −165.1 (4) |
C2B—C3—C4B—N1B | 10.8 (9) | C2D—C3D—C4D—N1D | 6.9 (9) |
C2B—C3—C4B—C5B | −168.3 (6) | C2D—C3D—C4D—C5D | −171.0 (6) |
C4B—N1B—C6B—C7B | −134.9 (4) | C4D—N1D—C6D—C7D | −150.4 (5) |
Si1B—N1B—C6B—C7B | 30.5 (4) | Si1D—N1D—C6D—C7D | 15.7 (5) |
C4B—N1B—C6B—C8C | 103.9 (5) | C4D—N1D—C6D—C8F | 87.9 (5) |
Si1B—N1B—C6B—C8C | −90.7 (4) | Si1D—N1D—C6D—C8F | −106.0 (4) |
Si1B—O2B—C7B—O3C | −168.1 (4) | Si1D—O2D—C7D—O3F | −178.8 (5) |
Si1B—O2B—C7B—C6B | 13.8 (5) | Si1D—O2D—C7D—C6D | −2.2 (6) |
N1B—C6B—C7B—O3C | 154.4 (4) | N1D—C6D—C7D—O3F | 168.0 (5) |
C8C—C6B—C7B—O3C | −85.2 (5) | C8F—C6D—C7D—O3F | −69.1 (7) |
N1B—C6B—C7B—O2B | −27.4 (5) | N1D—C6D—C7D—O2D | −8.6 (6) |
C8C—C6B—C7B—O2B | 93.0 (4) | C8F—C6D—C7D—O2D | 114.3 (5) |
N1B—C6B—C8C—C10C | 175.3 (4) | N1D—C6D—C8F—C9F | −171.5 (4) |
C7B—C6B—C8C—C10C | 58.7 (5) | C7D—C6D—C8F—C9F | 69.2 (5) |
N1B—C6B—C8C—C9C | −60.9 (5) | N1D—C6D—C8F—C10F | 62.4 (5) |
C7B—C6B—C8C—C9C | −177.5 (4) | C7D—C6D—C8F—C10F | −56.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5B···O3Ai | 0.98 | 2.39 | 3.326 (15) | 161 |
C5A—H5B···O3Bi | 0.98 | 2.33 | 3.297 (12) | 170 |
C1B—H1E···O2Bii | 0.98 | 2.64 | 3.591 (8) | 164 |
C3—H3B···O3Cii | 0.95 | 2.61 | 3.469 (6) | 150 |
C5B—H5E···O3Cii | 0.98 | 2.52 | 3.462 (6) | 162 |
C3C—H3C···O3Ei | 0.95 | 2.59 | 3.410 (12) | 145 |
C5C—H5H···O3Di | 0.98 | 2.40 | 3.360 (15) | 166 |
C5C—H5H···O3Ei | 0.98 | 2.34 | 3.301 (11) | 165 |
C5D—H5K···O3Fii | 0.98 | 2.41 | 3.200 (6) | 137 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |
(II-LT) Dimethyl[
N-(4-oxidopent-3-en-2-ylidene)valinato-
κ3O,
N,
O']silicon(II)
top
Crystal data top
C12H21NO3Si | Dx = 1.230 Mg m−3 |
Mr = 255.39 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 43033 reflections |
a = 22.9355 (7) Å | θ = 1.3–29.9° |
b = 8.1571 (2) Å | µ = 0.17 mm−1 |
c = 22.1230 (5) Å | T = 123 K |
V = 4138.93 (19) Å3 | Prism, colorless |
Z = 12 | 0.40 × 0.21 × 0.18 mm |
F(000) = 1656 | |
Data collection top
Stoe IPDS 2 diffractometer | 9511 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 8495 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.060 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
rotation method scans | h = −29→29 |
Absorption correction: integration (X-RED; Stoe & Cie, 2009) | k = −10→9 |
Tmin = 0.665, Tmax = 0.829 | l = −28→28 |
43033 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0424P)2 + 1.7433P]
where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.104 | (Δ/σ)max = 0.021 |
S = 1.11 | Δρmax = 0.22 e Å−3 |
9511 reflections | Δρmin = −0.27 e Å−3 |
478 parameters | Absolute structure: Flack x determined using 3434 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons & Flack, 2004) |
0 restraints | Absolute structure parameter: 0.02 (5) |
Special details top
Experimental. loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k
_exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 30 0 2 0.8411 30 4 1
0.6942 30 0 - 20 0.7847 - 1 5 30 1.1851 - 1 -5 30 1.1020 - 30 0 0 0.6588 - 30
- 4 0 0.8173 - 30 4 - 25 1.0964 - 30 4 1 0.9788 3 - 30 4 1.8743 0 0 - 30
0.9729 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Si1A | 0.63846 (3) | 0.28236 (9) | 0.41647 (3) | 0.01680 (15) | |
N1A | 0.70137 (10) | 0.1932 (3) | 0.37641 (10) | 0.0157 (4) | |
O1A | 0.60044 (8) | 0.0861 (2) | 0.41119 (9) | 0.0200 (4) | |
O2A | 0.68345 (9) | 0.4684 (2) | 0.41792 (10) | 0.0234 (4) | |
O3A | 0.77010 (9) | 0.5749 (2) | 0.39354 (11) | 0.0264 (5) | |
C1A | 0.58576 (15) | −0.1878 (4) | 0.44422 (17) | 0.0332 (7) | |
H1AA | 0.6086 | −0.2873 | 0.4519 | 0.050* | |
H1AB | 0.5557 | −0.2111 | 0.4139 | 0.050* | |
H1AC | 0.5672 | −0.1518 | 0.4819 | 0.050* | |
C2A | 0.62522 (13) | −0.0554 (3) | 0.42132 (12) | 0.0207 (5) | |
C3A | 0.68320 (12) | −0.0817 (3) | 0.40973 (13) | 0.0207 (5) | |
H3A | 0.6998 | −0.1844 | 0.4203 | 0.025* | |
C4A | 0.71916 (12) | 0.0384 (3) | 0.38265 (12) | 0.0170 (5) | |
C5A | 0.77813 (12) | −0.0165 (3) | 0.36127 (13) | 0.0222 (6) | |
H5AA | 0.7829 | −0.1337 | 0.3695 | 0.033* | |
H5AB | 0.8084 | 0.0455 | 0.3826 | 0.033* | |
H5AC | 0.7815 | 0.0031 | 0.3177 | 0.033* | |
C6A | 0.73960 (12) | 0.3191 (3) | 0.34851 (12) | 0.0180 (5) | |
H6A | 0.7810 | 0.2807 | 0.3482 | 0.022* | |
C7A | 0.73308 (12) | 0.4681 (3) | 0.38945 (13) | 0.0200 (5) | |
C8A | 0.71945 (13) | 0.3621 (4) | 0.28351 (13) | 0.0231 (6) | |
H8A | 0.6777 | 0.3970 | 0.2856 | 0.028* | |
C9A | 0.75484 (18) | 0.5052 (5) | 0.25782 (16) | 0.0398 (8) | |
H9AA | 0.7410 | 0.5310 | 0.2170 | 0.060* | |
H9AB | 0.7961 | 0.4748 | 0.2562 | 0.060* | |
H9AC | 0.7500 | 0.6015 | 0.2838 | 0.060* | |
C10A | 0.72330 (16) | 0.2156 (4) | 0.24123 (14) | 0.0338 (7) | |
H10A | 0.7059 | 0.2440 | 0.2022 | 0.051* | |
H10B | 0.7022 | 0.1228 | 0.2589 | 0.051* | |
H10C | 0.7643 | 0.1856 | 0.2354 | 0.051* | |
C11A | 0.57848 (13) | 0.3802 (3) | 0.37275 (14) | 0.0247 (6) | |
H11A | 0.5429 | 0.3813 | 0.3972 | 0.037* | |
H11B | 0.5716 | 0.3179 | 0.3356 | 0.037* | |
H11C | 0.5894 | 0.4929 | 0.3625 | 0.037* | |
C12A | 0.63737 (14) | 0.2759 (4) | 0.50095 (13) | 0.0284 (6) | |
H12A | 0.6022 | 0.3308 | 0.5158 | 0.043* | |
H12B | 0.6720 | 0.3318 | 0.5168 | 0.043* | |
H12C | 0.6374 | 0.1615 | 0.5145 | 0.043* | |
Si1B | 0.30684 (3) | 0.28980 (9) | 0.41285 (3) | 0.01629 (15) | |
N1B | 0.37120 (9) | 0.2007 (3) | 0.37501 (10) | 0.0161 (4) | |
O1B | 0.27004 (8) | 0.0917 (2) | 0.40874 (9) | 0.0195 (4) | |
O2B | 0.35105 (8) | 0.4783 (2) | 0.41281 (9) | 0.0218 (4) | |
O3B | 0.43847 (9) | 0.5833 (2) | 0.39117 (10) | 0.0277 (5) | |
C1B | 0.25603 (14) | −0.1812 (4) | 0.44293 (16) | 0.0285 (7) | |
H1BA | 0.2787 | −0.2820 | 0.4484 | 0.043* | |
H1BB | 0.2246 | −0.2009 | 0.4138 | 0.043* | |
H1BC | 0.2393 | −0.1479 | 0.4818 | 0.043* | |
C2B | 0.29487 (12) | −0.0487 (3) | 0.41987 (12) | 0.0198 (5) | |
C3B | 0.35327 (12) | −0.0742 (3) | 0.40937 (12) | 0.0199 (5) | |
H3B | 0.3700 | −0.1766 | 0.4204 | 0.024* | |
C4B | 0.38926 (12) | 0.0460 (3) | 0.38287 (12) | 0.0182 (5) | |
C5B | 0.44929 (12) | −0.0069 (3) | 0.36393 (13) | 0.0217 (6) | |
H5BA | 0.4540 | −0.1245 | 0.3715 | 0.033* | |
H5BB | 0.4785 | 0.0542 | 0.3872 | 0.033* | |
H5BC | 0.4546 | 0.0152 | 0.3207 | 0.033* | |
C6B | 0.40930 (12) | 0.3249 (3) | 0.34704 (12) | 0.0178 (5) | |
H6B | 0.4508 | 0.2875 | 0.3478 | 0.021* | |
C7B | 0.40163 (12) | 0.4761 (3) | 0.38653 (13) | 0.0198 (5) | |
C8B | 0.39025 (13) | 0.3643 (3) | 0.28137 (13) | 0.0223 (6) | |
H8B | 0.3485 | 0.3993 | 0.2824 | 0.027* | |
C9B | 0.42597 (18) | 0.5057 (5) | 0.25520 (16) | 0.0417 (9) | |
H9BA | 0.4130 | 0.5283 | 0.2138 | 0.063* | |
H9BB | 0.4673 | 0.4756 | 0.2549 | 0.063* | |
H9BC | 0.4205 | 0.6037 | 0.2801 | 0.063* | |
C10B | 0.39475 (16) | 0.2154 (4) | 0.24041 (13) | 0.0325 (7) | |
H10D | 0.3774 | 0.2408 | 0.2010 | 0.049* | |
H10E | 0.3739 | 0.1231 | 0.2588 | 0.049* | |
H10F | 0.4359 | 0.1862 | 0.2349 | 0.049* | |
C11B | 0.24688 (13) | 0.3824 (3) | 0.36753 (14) | 0.0236 (6) | |
H11D | 0.2094 | 0.3588 | 0.3869 | 0.035* | |
H11E | 0.2472 | 0.3358 | 0.3267 | 0.035* | |
H11F | 0.2525 | 0.5013 | 0.3651 | 0.035* | |
C12B | 0.30438 (13) | 0.2907 (4) | 0.49698 (13) | 0.0265 (6) | |
H12D | 0.2678 | 0.3409 | 0.5105 | 0.040* | |
H12E | 0.3374 | 0.3539 | 0.5127 | 0.040* | |
H12F | 0.3066 | 0.1779 | 0.5120 | 0.040* | |
Si1C | −0.02968 (3) | 0.25856 (9) | 0.40645 (3) | 0.01834 (15) | |
N1C | 0.03313 (10) | 0.1506 (2) | 0.37282 (9) | 0.0160 (4) | |
O1C | −0.06880 (9) | 0.0636 (2) | 0.41234 (9) | 0.0226 (4) | |
O2C | 0.01433 (9) | 0.4415 (2) | 0.39337 (10) | 0.0254 (4) | |
O3C | 0.09361 (11) | 0.5450 (3) | 0.34929 (13) | 0.0397 (6) | |
C1C | −0.08783 (15) | −0.2033 (4) | 0.45027 (14) | 0.0306 (7) | |
H1CA | −0.0674 | −0.3079 | 0.4557 | 0.046* | |
H1CB | −0.1203 | −0.2182 | 0.4220 | 0.046* | |
H1CC | −0.1029 | −0.1655 | 0.4893 | 0.046* | |
C2C | −0.04647 (13) | −0.0789 (3) | 0.42548 (12) | 0.0214 (6) | |
C3C | 0.01134 (13) | −0.1132 (3) | 0.41533 (13) | 0.0214 (6) | |
H3C | 0.0266 | −0.2150 | 0.4289 | 0.026* | |
C4C | 0.04853 (12) | −0.0036 (3) | 0.38566 (12) | 0.0178 (5) | |
C5C | 0.10794 (13) | −0.0673 (3) | 0.36788 (14) | 0.0241 (6) | |
H5CA | 0.1111 | −0.1833 | 0.3789 | 0.036* | |
H5CB | 0.1381 | −0.0046 | 0.3891 | 0.036* | |
H5CC | 0.1132 | −0.0551 | 0.3241 | 0.036* | |
C6C | 0.07432 (12) | 0.2568 (3) | 0.33992 (12) | 0.0184 (5) | |
H6C | 0.1149 | 0.2273 | 0.3524 | 0.022* | |
C7C | 0.06152 (13) | 0.4303 (3) | 0.36126 (14) | 0.0249 (6) | |
C8C | 0.06928 (12) | 0.2360 (4) | 0.27017 (12) | 0.0231 (6) | |
H8C | 0.0749 | 0.1169 | 0.2612 | 0.028* | |
C9C | 0.11780 (15) | 0.3289 (5) | 0.23754 (16) | 0.0375 (8) | |
H9CA | 0.1168 | 0.3022 | 0.1944 | 0.056* | |
H9CB | 0.1556 | 0.2971 | 0.2544 | 0.056* | |
H9CC | 0.1121 | 0.4471 | 0.2429 | 0.056* | |
C10C | 0.00968 (14) | 0.2836 (4) | 0.24615 (14) | 0.0320 (7) | |
H10G | 0.0077 | 0.2596 | 0.2028 | 0.048* | |
H10H | 0.0033 | 0.4010 | 0.2527 | 0.048* | |
H10I | −0.0204 | 0.2208 | 0.2674 | 0.048* | |
C11C | −0.09269 (13) | 0.3429 (4) | 0.36269 (15) | 0.0272 (6) | |
H11G | −0.1254 | 0.3635 | 0.3902 | 0.041* | |
H11H | −0.1046 | 0.2636 | 0.3318 | 0.041* | |
H11I | −0.0811 | 0.4457 | 0.3432 | 0.041* | |
C12C | −0.02842 (14) | 0.2859 (4) | 0.49034 (13) | 0.0290 (6) | |
H12G | −0.0672 | 0.3191 | 0.5044 | 0.043* | |
H12H | 0.0000 | 0.3706 | 0.5010 | 0.043* | |
H12I | −0.0175 | 0.1822 | 0.5096 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1A | 0.0165 (3) | 0.0149 (3) | 0.0190 (3) | 0.0023 (3) | 0.0013 (3) | −0.0013 (3) |
N1A | 0.0181 (10) | 0.0122 (9) | 0.0169 (10) | 0.0007 (8) | −0.0004 (8) | 0.0000 (8) |
O1A | 0.0176 (9) | 0.0168 (8) | 0.0257 (10) | 0.0020 (7) | 0.0022 (8) | 0.0010 (8) |
O2A | 0.0211 (10) | 0.0166 (9) | 0.0324 (11) | 0.0017 (7) | 0.0024 (9) | −0.0067 (9) |
O3A | 0.0265 (11) | 0.0161 (9) | 0.0365 (12) | −0.0037 (8) | −0.0017 (9) | −0.0029 (9) |
C1A | 0.0306 (17) | 0.0211 (14) | 0.0479 (19) | 0.0009 (13) | 0.0106 (15) | 0.0095 (14) |
C2A | 0.0264 (14) | 0.0165 (12) | 0.0193 (12) | 0.0013 (10) | 0.0027 (11) | 0.0015 (10) |
C3A | 0.0248 (14) | 0.0148 (11) | 0.0225 (14) | 0.0030 (10) | 0.0011 (11) | 0.0028 (10) |
C4A | 0.0187 (12) | 0.0151 (11) | 0.0172 (12) | 0.0020 (10) | −0.0029 (10) | −0.0027 (10) |
C5A | 0.0215 (14) | 0.0181 (12) | 0.0271 (14) | 0.0033 (11) | 0.0023 (12) | −0.0037 (11) |
C6A | 0.0186 (13) | 0.0153 (12) | 0.0200 (13) | −0.0009 (10) | 0.0013 (10) | 0.0008 (10) |
C7A | 0.0223 (13) | 0.0143 (12) | 0.0233 (13) | 0.0017 (10) | −0.0020 (11) | 0.0006 (10) |
C8A | 0.0258 (15) | 0.0238 (14) | 0.0198 (13) | −0.0027 (12) | −0.0009 (11) | 0.0030 (11) |
C9A | 0.051 (2) | 0.0380 (19) | 0.0305 (17) | −0.0124 (17) | 0.0043 (16) | 0.0082 (15) |
C10A | 0.050 (2) | 0.0303 (16) | 0.0212 (14) | −0.0031 (15) | −0.0024 (14) | −0.0021 (13) |
C11A | 0.0217 (14) | 0.0207 (13) | 0.0318 (15) | 0.0041 (11) | 0.0001 (12) | 0.0039 (12) |
C12A | 0.0268 (15) | 0.0373 (18) | 0.0209 (12) | −0.0011 (14) | 0.0034 (12) | −0.0054 (13) |
Si1B | 0.0172 (3) | 0.0149 (3) | 0.0168 (3) | 0.0022 (3) | 0.0015 (3) | −0.0006 (3) |
N1B | 0.0180 (10) | 0.0140 (10) | 0.0163 (10) | 0.0000 (8) | 0.0011 (8) | −0.0005 (8) |
O1B | 0.0193 (9) | 0.0166 (8) | 0.0228 (10) | 0.0012 (7) | 0.0003 (8) | 0.0001 (8) |
O2B | 0.0212 (10) | 0.0161 (9) | 0.0281 (10) | 0.0010 (7) | 0.0043 (8) | −0.0031 (8) |
O3B | 0.0260 (11) | 0.0167 (9) | 0.0404 (12) | −0.0020 (8) | 0.0034 (10) | −0.0029 (9) |
C1B | 0.0264 (15) | 0.0208 (14) | 0.0381 (17) | −0.0012 (12) | 0.0078 (13) | 0.0027 (13) |
C2B | 0.0248 (14) | 0.0159 (11) | 0.0187 (12) | 0.0006 (10) | 0.0002 (11) | 0.0010 (10) |
C3B | 0.0255 (14) | 0.0149 (11) | 0.0193 (13) | 0.0017 (10) | −0.0010 (11) | 0.0010 (10) |
C4B | 0.0203 (13) | 0.0181 (12) | 0.0163 (12) | 0.0028 (10) | −0.0029 (10) | −0.0018 (10) |
C5B | 0.0205 (13) | 0.0175 (12) | 0.0271 (14) | 0.0035 (10) | 0.0024 (11) | −0.0005 (11) |
C6B | 0.0169 (12) | 0.0159 (12) | 0.0205 (13) | −0.0010 (10) | 0.0002 (10) | −0.0005 (10) |
C7B | 0.0215 (13) | 0.0146 (11) | 0.0232 (13) | 0.0011 (10) | −0.0017 (11) | 0.0003 (10) |
C8B | 0.0239 (14) | 0.0221 (13) | 0.0209 (13) | 0.0005 (11) | 0.0018 (11) | 0.0028 (11) |
C9B | 0.055 (2) | 0.0401 (19) | 0.0295 (17) | −0.0140 (18) | 0.0067 (16) | 0.0112 (15) |
C10B | 0.0441 (19) | 0.0324 (16) | 0.0209 (13) | 0.0027 (15) | −0.0028 (13) | −0.0021 (13) |
C11B | 0.0226 (14) | 0.0192 (13) | 0.0289 (15) | 0.0036 (11) | −0.0027 (12) | 0.0042 (12) |
C12B | 0.0260 (15) | 0.0339 (16) | 0.0197 (13) | −0.0027 (13) | 0.0031 (11) | −0.0045 (12) |
Si1C | 0.0184 (3) | 0.0163 (3) | 0.0203 (3) | 0.0012 (3) | 0.0010 (3) | −0.0013 (3) |
N1C | 0.0187 (11) | 0.0135 (9) | 0.0158 (10) | 0.0005 (9) | −0.0017 (9) | −0.0005 (8) |
O1C | 0.0221 (10) | 0.0195 (9) | 0.0262 (10) | −0.0001 (8) | 0.0019 (8) | 0.0012 (8) |
O2C | 0.0237 (10) | 0.0155 (8) | 0.0370 (11) | 0.0003 (8) | 0.0054 (9) | −0.0030 (8) |
O3C | 0.0343 (13) | 0.0173 (10) | 0.0675 (17) | −0.0064 (9) | 0.0124 (12) | −0.0018 (11) |
C1C | 0.0377 (18) | 0.0241 (14) | 0.0299 (15) | −0.0072 (13) | 0.0045 (13) | 0.0049 (12) |
C2C | 0.0305 (15) | 0.0172 (12) | 0.0165 (12) | −0.0028 (11) | −0.0007 (11) | 0.0001 (10) |
C3C | 0.0291 (15) | 0.0154 (11) | 0.0198 (12) | 0.0012 (10) | −0.0024 (11) | 0.0019 (10) |
C4C | 0.0224 (13) | 0.0154 (11) | 0.0157 (11) | 0.0022 (10) | −0.0040 (10) | −0.0020 (9) |
C5C | 0.0252 (15) | 0.0167 (12) | 0.0304 (15) | 0.0044 (11) | −0.0030 (12) | −0.0017 (11) |
C6C | 0.0166 (12) | 0.0161 (12) | 0.0223 (12) | −0.0014 (10) | 0.0002 (10) | 0.0004 (10) |
C7C | 0.0236 (15) | 0.0162 (12) | 0.0349 (16) | −0.0004 (11) | −0.0017 (12) | −0.0003 (11) |
C8C | 0.0245 (14) | 0.0237 (13) | 0.0211 (12) | −0.0017 (12) | 0.0011 (11) | 0.0039 (11) |
C9C | 0.0315 (17) | 0.048 (2) | 0.0331 (17) | −0.0059 (16) | 0.0085 (14) | 0.0082 (15) |
C10C | 0.0318 (16) | 0.0405 (18) | 0.0235 (13) | −0.0009 (14) | −0.0015 (12) | 0.0093 (13) |
C11C | 0.0228 (14) | 0.0248 (14) | 0.0341 (16) | 0.0054 (12) | 0.0006 (12) | 0.0057 (12) |
C12C | 0.0262 (15) | 0.0354 (16) | 0.0252 (14) | −0.0037 (14) | 0.0023 (12) | −0.0082 (12) |
Geometric parameters (Å, º) top
Si1A—O1A | 1.826 (2) | C5B—H5BC | 0.9800 |
Si1A—O2A | 1.835 (2) | C6B—C7B | 1.522 (4) |
Si1A—N1A | 1.843 (2) | C6B—C8B | 1.551 (4) |
Si1A—C11A | 1.861 (3) | C6B—H6B | 1.0000 |
Si1A—C12A | 1.870 (3) | C8B—C10B | 1.519 (4) |
N1A—C4A | 1.335 (3) | C8B—C9B | 1.528 (4) |
N1A—C6A | 1.485 (3) | C8B—H8B | 1.0000 |
O1A—C2A | 1.306 (3) | C9B—H9BA | 0.9800 |
O2A—C7A | 1.301 (3) | C9B—H9BB | 0.9800 |
O3A—C7A | 1.220 (3) | C9B—H9BC | 0.9800 |
C1A—C2A | 1.498 (4) | C10B—H10D | 0.9800 |
C1A—H1AA | 0.9800 | C10B—H10E | 0.9800 |
C1A—H1AB | 0.9800 | C10B—H10F | 0.9800 |
C1A—H1AC | 0.9800 | C11B—H11D | 0.9800 |
C2A—C3A | 1.371 (4) | C11B—H11E | 0.9800 |
C3A—C4A | 1.413 (4) | C11B—H11F | 0.9800 |
C3A—H3A | 0.9500 | C12B—H12D | 0.9800 |
C4A—C5A | 1.501 (4) | C12B—H12E | 0.9800 |
C5A—H5AA | 0.9800 | C12B—H12F | 0.9800 |
C5A—H5AB | 0.9800 | Si1C—O2C | 1.825 (2) |
C5A—H5AC | 0.9800 | Si1C—O1C | 1.830 (2) |
C6A—C7A | 1.523 (4) | Si1C—N1C | 1.845 (2) |
C6A—C8A | 1.551 (4) | Si1C—C12C | 1.869 (3) |
C6A—H6A | 1.0000 | Si1C—C11C | 1.870 (3) |
C8A—C10A | 1.520 (4) | N1C—C4C | 1.337 (3) |
C8A—C9A | 1.531 (4) | N1C—C6C | 1.474 (3) |
C8A—H8A | 1.0000 | O1C—C2C | 1.303 (3) |
C9A—H9AA | 0.9800 | O2C—C7C | 1.298 (4) |
C9A—H9AB | 0.9800 | O3C—C7C | 1.219 (4) |
C9A—H9AC | 0.9800 | C1C—C2C | 1.493 (4) |
C10A—H10A | 0.9800 | C1C—H1CA | 0.9800 |
C10A—H10B | 0.9800 | C1C—H1CB | 0.9800 |
C10A—H10C | 0.9800 | C1C—H1CC | 0.9800 |
C11A—H11A | 0.9800 | C2C—C3C | 1.373 (4) |
C11A—H11B | 0.9800 | C3C—C4C | 1.399 (4) |
C11A—H11C | 0.9800 | C3C—H3C | 0.9500 |
C12A—H12A | 0.9800 | C4C—C5C | 1.510 (4) |
C12A—H12B | 0.9800 | C5C—H5CA | 0.9800 |
C12A—H12C | 0.9800 | C5C—H5CB | 0.9800 |
Si1B—O1B | 1.826 (2) | C5C—H5CC | 0.9800 |
Si1B—O2B | 1.842 (2) | C6C—C7C | 1.521 (4) |
Si1B—N1B | 1.846 (2) | C6C—C8C | 1.557 (4) |
Si1B—C11B | 1.862 (3) | C6C—H6C | 1.0000 |
Si1B—C12B | 1.862 (3) | C8C—C10C | 1.517 (4) |
N1B—C4B | 1.339 (3) | C8C—C9C | 1.528 (4) |
N1B—C6B | 1.474 (3) | C8C—H8C | 1.0000 |
O1B—C2B | 1.302 (3) | C9C—H9CA | 0.9800 |
O2B—C7B | 1.298 (3) | C9C—H9CB | 0.9800 |
O3B—C7B | 1.220 (3) | C9C—H9CC | 0.9800 |
C1B—C2B | 1.491 (4) | C10C—H10G | 0.9800 |
C1B—H1BA | 0.9800 | C10C—H10H | 0.9800 |
C1B—H1BB | 0.9800 | C10C—H10I | 0.9800 |
C1B—H1BC | 0.9800 | C11C—H11G | 0.9800 |
C2B—C3B | 1.375 (4) | C11C—H11H | 0.9800 |
C3B—C4B | 1.410 (4) | C11C—H11I | 0.9800 |
C3B—H3B | 0.9500 | C12C—H12G | 0.9800 |
C4B—C5B | 1.502 (4) | C12C—H12H | 0.9800 |
C5B—H5BA | 0.9800 | C12C—H12I | 0.9800 |
C5B—H5BB | 0.9800 | | |
| | | |
O1A—Si1A—O2A | 173.77 (10) | C7B—C6B—C8B | 109.7 (2) |
O1A—Si1A—N1A | 89.84 (9) | N1B—C6B—H6B | 110.3 |
O2A—Si1A—N1A | 83.95 (9) | C7B—C6B—H6B | 110.3 |
O1A—Si1A—C11A | 89.40 (11) | C8B—C6B—H6B | 110.3 |
O2A—Si1A—C11A | 94.02 (11) | O3B—C7B—O2B | 124.8 (3) |
N1A—Si1A—C11A | 119.86 (12) | O3B—C7B—C6B | 123.3 (3) |
O1A—Si1A—C12A | 91.87 (12) | O2B—C7B—C6B | 111.8 (2) |
O2A—Si1A—C12A | 90.77 (13) | C10B—C8B—C9B | 109.9 (3) |
N1A—Si1A—C12A | 118.68 (13) | C10B—C8B—C6B | 112.0 (2) |
C11A—Si1A—C12A | 121.44 (14) | C9B—C8B—C6B | 111.1 (3) |
C4A—N1A—C6A | 121.1 (2) | C10B—C8B—H8B | 107.9 |
C4A—N1A—Si1A | 124.27 (19) | C9B—C8B—H8B | 107.9 |
C6A—N1A—Si1A | 112.92 (16) | C6B—C8B—H8B | 107.9 |
C2A—O1A—Si1A | 123.77 (18) | C8B—C9B—H9BA | 109.5 |
C7A—O2A—Si1A | 118.80 (17) | C8B—C9B—H9BB | 109.5 |
C2A—C1A—H1AA | 109.5 | H9BA—C9B—H9BB | 109.5 |
C2A—C1A—H1AB | 109.5 | C8B—C9B—H9BC | 109.5 |
H1AA—C1A—H1AB | 109.5 | H9BA—C9B—H9BC | 109.5 |
C2A—C1A—H1AC | 109.5 | H9BB—C9B—H9BC | 109.5 |
H1AA—C1A—H1AC | 109.5 | C8B—C10B—H10D | 109.5 |
H1AB—C1A—H1AC | 109.5 | C8B—C10B—H10E | 109.5 |
O1A—C2A—C3A | 121.9 (2) | H10D—C10B—H10E | 109.5 |
O1A—C2A—C1A | 115.6 (2) | C8B—C10B—H10F | 109.5 |
C3A—C2A—C1A | 122.4 (2) | H10D—C10B—H10F | 109.5 |
C2A—C3A—C4A | 122.5 (2) | H10E—C10B—H10F | 109.5 |
C2A—C3A—H3A | 118.8 | Si1B—C11B—H11D | 109.5 |
C4A—C3A—H3A | 118.8 | Si1B—C11B—H11E | 109.5 |
N1A—C4A—C3A | 121.4 (2) | H11D—C11B—H11E | 109.5 |
N1A—C4A—C5A | 121.6 (2) | Si1B—C11B—H11F | 109.5 |
C3A—C4A—C5A | 116.9 (2) | H11D—C11B—H11F | 109.5 |
C4A—C5A—H5AA | 109.5 | H11E—C11B—H11F | 109.5 |
C4A—C5A—H5AB | 109.5 | Si1B—C12B—H12D | 109.5 |
H5AA—C5A—H5AB | 109.5 | Si1B—C12B—H12E | 109.5 |
C4A—C5A—H5AC | 109.5 | H12D—C12B—H12E | 109.5 |
H5AA—C5A—H5AC | 109.5 | Si1B—C12B—H12F | 109.5 |
H5AB—C5A—H5AC | 109.5 | H12D—C12B—H12F | 109.5 |
N1A—C6A—C7A | 104.3 (2) | H12E—C12B—H12F | 109.5 |
N1A—C6A—C8A | 111.5 (2) | O2C—Si1C—O1C | 173.17 (10) |
C7A—C6A—C8A | 110.0 (2) | O2C—Si1C—N1C | 83.95 (10) |
N1A—C6A—H6A | 110.3 | O1C—Si1C—N1C | 89.81 (10) |
C7A—C6A—H6A | 110.3 | O2C—Si1C—C12C | 92.95 (13) |
C8A—C6A—H6A | 110.3 | O1C—Si1C—C12C | 92.32 (12) |
O3A—C7A—O2A | 124.9 (3) | N1C—Si1C—C12C | 116.44 (13) |
O3A—C7A—C6A | 123.1 (3) | O2C—Si1C—C11C | 92.55 (12) |
O2A—C7A—C6A | 112.1 (2) | O1C—Si1C—C11C | 88.71 (12) |
C10A—C8A—C9A | 109.9 (3) | N1C—Si1C—C11C | 124.74 (13) |
C10A—C8A—C6A | 112.0 (2) | C12C—Si1C—C11C | 118.81 (15) |
C9A—C8A—C6A | 111.0 (3) | C4C—N1C—C6C | 119.2 (2) |
C10A—C8A—H8A | 107.9 | C4C—N1C—Si1C | 124.72 (19) |
C9A—C8A—H8A | 107.9 | C6C—N1C—Si1C | 114.76 (16) |
C6A—C8A—H8A | 107.9 | C2C—O1C—Si1C | 126.75 (19) |
C8A—C9A—H9AA | 109.5 | C7C—O2C—Si1C | 119.37 (18) |
C8A—C9A—H9AB | 109.5 | C2C—C1C—H1CA | 109.5 |
H9AA—C9A—H9AB | 109.5 | C2C—C1C—H1CB | 109.5 |
C8A—C9A—H9AC | 109.5 | H1CA—C1C—H1CB | 109.5 |
H9AA—C9A—H9AC | 109.5 | C2C—C1C—H1CC | 109.5 |
H9AB—C9A—H9AC | 109.5 | H1CA—C1C—H1CC | 109.5 |
C8A—C10A—H10A | 109.5 | H1CB—C1C—H1CC | 109.5 |
C8A—C10A—H10B | 109.5 | O1C—C2C—C3C | 121.6 (2) |
H10A—C10A—H10B | 109.5 | O1C—C2C—C1C | 116.0 (3) |
C8A—C10A—H10C | 109.5 | C3C—C2C—C1C | 122.3 (3) |
H10A—C10A—H10C | 109.5 | C2C—C3C—C4C | 122.4 (2) |
H10B—C10A—H10C | 109.5 | C2C—C3C—H3C | 118.8 |
Si1A—C11A—H11A | 109.5 | C4C—C3C—H3C | 118.8 |
Si1A—C11A—H11B | 109.5 | N1C—C4C—C3C | 122.7 (3) |
H11A—C11A—H11B | 109.5 | N1C—C4C—C5C | 120.4 (2) |
Si1A—C11A—H11C | 109.5 | C3C—C4C—C5C | 116.9 (2) |
H11A—C11A—H11C | 109.5 | C4C—C5C—H5CA | 109.5 |
H11B—C11A—H11C | 109.5 | C4C—C5C—H5CB | 109.5 |
Si1A—C12A—H12A | 109.5 | H5CA—C5C—H5CB | 109.5 |
Si1A—C12A—H12B | 109.5 | C4C—C5C—H5CC | 109.5 |
H12A—C12A—H12B | 109.5 | H5CA—C5C—H5CC | 109.5 |
Si1A—C12A—H12C | 109.5 | H5CB—C5C—H5CC | 109.5 |
H12A—C12A—H12C | 109.5 | N1C—C6C—C7C | 105.7 (2) |
H12B—C12A—H12C | 109.5 | N1C—C6C—C8C | 112.2 (2) |
O1B—Si1B—O2B | 173.50 (10) | C7C—C6C—C8C | 113.3 (2) |
O1B—Si1B—N1B | 89.91 (9) | N1C—C6C—H6C | 108.5 |
O2B—Si1B—N1B | 83.59 (9) | C7C—C6C—H6C | 108.5 |
O1B—Si1B—C11B | 89.47 (11) | C8C—C6C—H6C | 108.5 |
O2B—Si1B—C11B | 93.88 (12) | O3C—C7C—O2C | 124.6 (3) |
N1B—Si1B—C11B | 120.40 (12) | O3C—C7C—C6C | 122.0 (3) |
O1B—Si1B—C12B | 92.25 (12) | O2C—C7C—C6C | 113.4 (2) |
O2B—Si1B—C12B | 90.80 (12) | C10C—C8C—C9C | 111.3 (2) |
N1B—Si1B—C12B | 118.62 (12) | C10C—C8C—C6C | 112.7 (2) |
C11B—Si1B—C12B | 120.95 (14) | C9C—C8C—C6C | 111.1 (2) |
C4B—N1B—C6B | 121.2 (2) | C10C—C8C—H8C | 107.1 |
C4B—N1B—Si1B | 124.02 (18) | C9C—C8C—H8C | 107.1 |
C6B—N1B—Si1B | 113.18 (16) | C6C—C8C—H8C | 107.1 |
C2B—O1B—Si1B | 124.53 (18) | C8C—C9C—H9CA | 109.5 |
C7B—O2B—Si1B | 118.72 (17) | C8C—C9C—H9CB | 109.5 |
C2B—C1B—H1BA | 109.5 | H9CA—C9C—H9CB | 109.5 |
C2B—C1B—H1BB | 109.5 | C8C—C9C—H9CC | 109.5 |
H1BA—C1B—H1BB | 109.5 | H9CA—C9C—H9CC | 109.5 |
C2B—C1B—H1BC | 109.5 | H9CB—C9C—H9CC | 109.5 |
H1BA—C1B—H1BC | 109.5 | C8C—C10C—H10G | 109.5 |
H1BB—C1B—H1BC | 109.5 | C8C—C10C—H10H | 109.5 |
O1B—C2B—C3B | 121.8 (2) | H10G—C10C—H10H | 109.5 |
O1B—C2B—C1B | 116.2 (2) | C8C—C10C—H10I | 109.5 |
C3B—C2B—C1B | 122.0 (2) | H10G—C10C—H10I | 109.5 |
C2B—C3B—C4B | 122.4 (2) | H10H—C10C—H10I | 109.5 |
C2B—C3B—H3B | 118.8 | Si1C—C11C—H11G | 109.5 |
C4B—C3B—H3B | 118.8 | Si1C—C11C—H11H | 109.5 |
N1B—C4B—C3B | 121.9 (2) | H11G—C11C—H11H | 109.5 |
N1B—C4B—C5B | 121.2 (2) | Si1C—C11C—H11I | 109.5 |
C3B—C4B—C5B | 116.9 (2) | H11G—C11C—H11I | 109.5 |
C4B—C5B—H5BA | 109.5 | H11H—C11C—H11I | 109.5 |
C4B—C5B—H5BB | 109.5 | Si1C—C12C—H12G | 109.5 |
H5BA—C5B—H5BB | 109.5 | Si1C—C12C—H12H | 109.5 |
C4B—C5B—H5BC | 109.5 | H12G—C12C—H12H | 109.5 |
H5BA—C5B—H5BC | 109.5 | Si1C—C12C—H12I | 109.5 |
H5BB—C5B—H5BC | 109.5 | H12G—C12C—H12I | 109.5 |
N1B—C6B—C7B | 104.3 (2) | H12H—C12C—H12I | 109.5 |
N1B—C6B—C8B | 111.6 (2) | | |
| | | |
O1A—Si1A—N1A—C4A | −35.2 (2) | Si1B—N1B—C4B—C3B | 15.4 (4) |
O2A—Si1A—N1A—C4A | 144.4 (2) | C6B—N1B—C4B—C5B | 0.5 (4) |
C11A—Si1A—N1A—C4A | −124.4 (2) | Si1B—N1B—C4B—C5B | −164.3 (2) |
C12A—Si1A—N1A—C4A | 56.8 (3) | C2B—C3B—C4B—N1B | 10.7 (4) |
O1A—Si1A—N1A—C6A | 159.48 (18) | C2B—C3B—C4B—C5B | −169.6 (3) |
O2A—Si1A—N1A—C6A | −20.92 (18) | C4B—N1B—C6B—C7B | −136.1 (2) |
C11A—Si1A—N1A—C6A | 70.3 (2) | Si1B—N1B—C6B—C7B | 30.2 (2) |
C12A—Si1A—N1A—C6A | −108.5 (2) | C4B—N1B—C6B—C8B | 105.5 (3) |
N1A—Si1A—O1A—C2A | 43.3 (2) | Si1B—N1B—C6B—C8B | −88.2 (2) |
C11A—Si1A—O1A—C2A | 163.1 (2) | Si1B—O2B—C7B—O3B | −168.3 (2) |
C12A—Si1A—O1A—C2A | −75.4 (2) | Si1B—O2B—C7B—C6B | 13.5 (3) |
N1A—Si1A—O2A—C7A | 5.2 (2) | N1B—C6B—C7B—O3B | 154.6 (3) |
C11A—Si1A—O2A—C7A | −114.5 (2) | C8B—C6B—C7B—O3B | −85.6 (3) |
C12A—Si1A—O2A—C7A | 123.9 (2) | N1B—C6B—C7B—O2B | −27.1 (3) |
Si1A—O1A—C2A—C3A | −30.6 (4) | C8B—C6B—C7B—O2B | 92.6 (3) |
Si1A—O1A—C2A—C1A | 151.5 (2) | N1B—C6B—C8B—C10B | −62.6 (3) |
O1A—C2A—C3A—C4A | −4.1 (4) | C7B—C6B—C8B—C10B | −177.7 (2) |
C1A—C2A—C3A—C4A | 173.7 (3) | N1B—C6B—C8B—C9B | 174.1 (3) |
C6A—N1A—C4A—C3A | 179.3 (2) | C7B—C6B—C8B—C9B | 58.9 (3) |
Si1A—N1A—C4A—C3A | 15.2 (4) | O2C—Si1C—N1C—C4C | 151.3 (2) |
C6A—N1A—C4A—C5A | −0.7 (4) | O1C—Si1C—N1C—C4C | −31.5 (2) |
Si1A—N1A—C4A—C5A | −164.9 (2) | C12C—Si1C—N1C—C4C | 61.0 (2) |
C2A—C3A—C4A—N1A | 11.8 (4) | C11C—Si1C—N1C—C4C | −119.8 (2) |
C2A—C3A—C4A—C5A | −168.2 (3) | O2C—Si1C—N1C—C6C | −15.68 (18) |
C4A—N1A—C6A—C7A | −135.9 (2) | O1C—Si1C—N1C—C6C | 161.53 (18) |
Si1A—N1A—C6A—C7A | 29.9 (2) | C12C—Si1C—N1C—C6C | −106.0 (2) |
C4A—N1A—C6A—C8A | 105.5 (3) | C11C—Si1C—N1C—C6C | 73.2 (2) |
Si1A—N1A—C6A—C8A | −88.7 (2) | N1C—Si1C—O1C—C2C | 36.9 (2) |
Si1A—O2A—C7A—O3A | −169.8 (2) | C12C—Si1C—O1C—C2C | −79.5 (2) |
Si1A—O2A—C7A—C6A | 11.5 (3) | C11C—Si1C—O1C—C2C | 161.7 (2) |
N1A—C6A—C7A—O3A | 155.6 (3) | N1C—Si1C—O2C—C7C | 9.9 (2) |
C8A—C6A—C7A—O3A | −84.8 (3) | C12C—Si1C—O2C—C7C | 126.2 (2) |
N1A—C6A—C7A—O2A | −25.7 (3) | C11C—Si1C—O2C—C7C | −114.8 (2) |
C8A—C6A—C7A—O2A | 93.9 (3) | Si1C—O1C—C2C—C3C | −24.3 (4) |
N1A—C6A—C8A—C10A | −63.0 (3) | Si1C—O1C—C2C—C1C | 157.5 (2) |
C7A—C6A—C8A—C10A | −178.2 (2) | O1C—C2C—C3C—C4C | −5.7 (4) |
N1A—C6A—C8A—C9A | 173.7 (3) | C1C—C2C—C3C—C4C | 172.4 (3) |
C7A—C6A—C8A—C9A | 58.5 (3) | C6C—N1C—C4C—C3C | −178.3 (2) |
O1B—Si1B—N1B—C4B | −34.4 (2) | Si1C—N1C—C4C—C3C | 15.2 (4) |
O2B—Si1B—N1B—C4B | 145.5 (2) | C6C—N1C—C4C—C5C | 1.3 (3) |
C11B—Si1B—N1B—C4B | −123.8 (2) | Si1C—N1C—C4C—C5C | −165.15 (19) |
C12B—Si1B—N1B—C4B | 58.1 (3) | C2C—C3C—C4C—N1C | 9.9 (4) |
O1B—Si1B—N1B—C6B | 159.72 (18) | C2C—C3C—C4C—C5C | −169.8 (3) |
O2B—Si1B—N1B—C6B | −20.36 (18) | C4C—N1C—C6C—C7C | −150.2 (2) |
C11B—Si1B—N1B—C6B | 70.4 (2) | Si1C—N1C—C6C—C7C | 17.6 (3) |
C12B—Si1B—N1B—C6B | −107.8 (2) | C4C—N1C—C6C—C8C | 86.0 (3) |
N1B—Si1B—O1B—C2B | 42.3 (2) | Si1C—N1C—C6C—C8C | −106.3 (2) |
C11B—Si1B—O1B—C2B | 162.7 (2) | Si1C—O2C—C7C—O3C | 179.2 (3) |
C12B—Si1B—O1B—C2B | −76.3 (2) | Si1C—O2C—C7C—C6C | −1.7 (3) |
N1B—Si1B—O2B—C7B | 3.6 (2) | N1C—C6C—C7C—O3C | 169.1 (3) |
C11B—Si1B—O2B—C7B | −116.6 (2) | C8C—C6C—C7C—O3C | −67.7 (4) |
C12B—Si1B—O2B—C7B | 122.3 (2) | N1C—C6C—C7C—O2C | −10.1 (3) |
Si1B—O1B—C2B—C3B | −29.9 (4) | C8C—C6C—C7C—O2C | 113.1 (3) |
Si1B—O1B—C2B—C1B | 151.7 (2) | N1C—C6C—C8C—C10C | 62.1 (3) |
O1B—C2B—C3B—C4B | −3.6 (4) | C7C—C6C—C8C—C10C | −57.5 (3) |
C1B—C2B—C3B—C4B | 174.6 (3) | N1C—C6C—C8C—C9C | −172.2 (2) |
C6B—N1B—C4B—C3B | −179.8 (2) | C7C—C6C—C8C—C9C | 68.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···O3Ai | 0.95 | 2.61 | 3.457 (3) | 149 |
C5A—H5AA···O3Ai | 0.98 | 2.45 | 3.414 (3) | 167 |
C3B—H3B···O3Bi | 0.95 | 2.59 | 3.433 (3) | 148 |
C5B—H5BA···O3Bi | 0.98 | 2.45 | 3.406 (3) | 165 |
C5C—H5CA···O3Ci | 0.98 | 2.35 | 3.207 (4) | 146 |
Symmetry code: (i) x, y−1, z. |
Selected torsion angles (°) for the three crystallographically
independent molecules in (II-LT) topMolecule | A | B | C |
N1—C6—C8—C9 | 173.7 (3) | 174.1 (3) | -172.2 (2) |
N1—C6—C8—C10 | -63.1 (3) | -62.6 (3) | 62.1 (3) |
O2—Si1—O1—C2 | 39.6 (8) | 41.4 (8) | 60.9 (8) |