Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028169/jh2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028169/jh20263sup2.hkl |
CCDC reference: 618251
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C32H26Si | Z = 2 |
Mr = 438.62 | F(000) = 464 |
Triclinic, P1 | Dx = 1.195 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.877 (3) Å | Cell parameters from 25 reflections |
b = 10.633 (2) Å | θ = 3.5–25.2° |
c = 13.693 (2) Å | µ = 0.96 mm−1 |
α = 67.620 (14)° | T = 295 K |
β = 84.657 (18)° | Prism, colorless |
γ = 66.77 (2)° | 0.50 × 0.30 × 0.25 mm |
V = 1219.2 (5) Å3 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.013 |
Radiation source: normal-focus sealed tube | θmax = 69.9°, θmin = 3.5° |
Graphite monochromator | h = −11→12 |
non–profiled ω/2θ scans | k = −11→12 |
7796 measured reflections | l = −12→16 |
4604 independent reflections | 3 standard reflections every 94 reflections |
4113 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0506P)2 + 0.2363P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max < 0.001 |
wR(F2) = 0.101 | Δρmax = 0.23 e Å−3 |
S = 1.03 | Δρmin = −0.20 e Å−3 |
4604 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
299 parameters | Extinction coefficient: 0.0250 (10) |
0 restraints |
Experimental. (1): 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 3.95 (s, 4H), 7.05–7.26 (m, 14H); 13C NMR (75.4 MHz, CDCl3, δ, p.p.m.): 39.0 (CH2), 126.0 (CH), 126.6 (CH), 128.4 (CH), 128.8 (CH), 130.6 (CH), 138.9 (C), 140.8 (C). (3): 1H NMR (500 MHz, CDCl3, δ, p.p.m.): 4.36 (s, 2H), 6.71 (d, J = 8 Hz, 2H), 6.93 (t, J = 8 Hz, 2H), 7.05 (m, 6H), 7.13 (m, 5H), 7.25 (m, 4H), 7.42 (bt, J = 7 Hz, 2H), 7.47 (bt, J = 7 Hz, 1H), 7.66 (d, J = 8 Hz, 2H); 13C NMR (125.7 MHz, CDCl3, δ, p.p.m.): 41.59 (CH), 124.82 (CH), 126.88 (CH), 127.07 (CH), 128.20(CH), 128.22 (CH), 128.27 (CH), 128.87 (CH), 129.59 (C), 130.03 (C), 130.49(C), 134.38 (C), 135.05 (CH), 136.36 (CH), 141.83 (C), 144.28 (C) |
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. |
x | y | z | Uiso*/Ueq | ||
Si | 0.43091 (4) | 0.68959 (4) | 0.73198 (3) | 0.04569 (13) | |
C22 | 0.27888 (14) | 0.86421 (14) | 0.64767 (10) | 0.0466 (3) | |
C27 | 0.16428 (16) | 0.95296 (16) | 0.69054 (12) | 0.0558 (3) | |
H27 | 0.1606 | 0.9231 | 0.7637 | 0.067* | |
C16 | 0.56546 (14) | 0.60922 (14) | 0.64593 (11) | 0.0485 (3) | |
C23 | 0.27846 (16) | 0.91449 (15) | 0.53762 (11) | 0.0528 (3) | |
H23 | 0.3526 | 0.8585 | 0.5064 | 0.063* | |
C24 | 0.17074 (18) | 1.04549 (17) | 0.47352 (12) | 0.0627 (4) | |
H24 | 0.1735 | 1.0767 | 0.4003 | 0.075* | |
C28 | 0.25036 (16) | 0.50845 (16) | 0.80844 (11) | 0.0555 (3) | |
C33 | 0.10765 (18) | 0.60581 (18) | 0.76522 (13) | 0.0658 (4) | |
H33 | 0.0768 | 0.7049 | 0.7549 | 0.079* | |
C5 | 0.38919 (17) | 0.72624 (16) | 0.91117 (11) | 0.0571 (4) | |
C10 | 0.57759 (16) | 0.83369 (16) | 0.81243 (11) | 0.0535 (3) | |
C21 | 0.58560 (19) | 0.47552 (16) | 0.63999 (14) | 0.0641 (4) | |
H21 | 0.535 | 0.4201 | 0.6838 | 0.077* | |
C26 | 0.05716 (16) | 1.08338 (16) | 0.62663 (13) | 0.0609 (4) | |
H26 | −0.0172 | 1.1407 | 0.6569 | 0.073* | |
C4 | 0.30808 (17) | 0.64298 (16) | 0.91202 (11) | 0.0572 (4) | |
C17 | 0.64621 (17) | 0.68624 (18) | 0.57996 (14) | 0.0625 (4) | |
H17 | 0.637 | 0.7752 | 0.5828 | 0.075* | |
C15 | 0.50363 (18) | 0.97942 (17) | 0.74465 (14) | 0.0643 (4) | |
H15 | 0.4126 | 1.0066 | 0.7119 | 0.077* | |
C19 | 0.7551 (2) | 0.50218 (19) | 0.50561 (15) | 0.0725 (5) | |
H19 | 0.8172 | 0.467 | 0.4583 | 0.087* | |
C1 | 0.51491 (16) | 0.71737 (15) | 0.83767 (11) | 0.0537 (3) | |
H1 | 0.5959 | 0.6228 | 0.8745 | 0.064* | |
C11 | 0.71408 (19) | 0.7988 (2) | 0.85753 (15) | 0.0740 (5) | |
H11 | 0.7675 | 0.7023 | 0.9029 | 0.089* | |
C14 | 0.5618 (2) | 1.08499 (18) | 0.72472 (14) | 0.0679 (4) | |
H14 | 0.5095 | 1.1818 | 0.6795 | 0.081* | |
C25 | 0.05989 (18) | 1.12922 (16) | 0.51803 (13) | 0.0639 (4) | |
H25 | −0.0132 | 1.2167 | 0.4751 | 0.077* | |
C32 | 0.0112 (2) | 0.5578 (2) | 0.73738 (14) | 0.0742 (5) | |
H32 | −0.0838 | 0.6245 | 0.7095 | 0.089* | |
C3 | 0.35802 (16) | 0.55839 (15) | 0.83785 (11) | 0.0536 (3) | |
H3 | 0.4444 | 0.4688 | 0.8742 | 0.064* | |
C6 | 0.3457 (2) | 0.8162 (2) | 0.96970 (13) | 0.0744 (5) | |
H6 | 0.3988 | 0.8716 | 0.9695 | 0.089* | |
C29 | 0.2910 (2) | 0.36132 (18) | 0.82231 (14) | 0.0687 (4) | |
H29 | 0.3848 | 0.2932 | 0.8519 | 0.082* | |
C20 | 0.6792 (2) | 0.42314 (19) | 0.57040 (16) | 0.0767 (5) | |
H20C | 0.6906 | 0.3335 | 0.5677 | 0.092* | |
C8 | 0.1448 (3) | 0.7397 (3) | 1.03046 (15) | 0.0917 (6) | |
H8 | 0.0632 | 0.7442 | 1.0709 | 0.11* | |
C31 | 0.0547 (2) | 0.4124 (2) | 0.75065 (15) | 0.0798 (5) | |
H31 | −0.01 | 0.3806 | 0.7311 | 0.096* | |
C18 | 0.73960 (19) | 0.6336 (2) | 0.51045 (15) | 0.0730 (5) | |
H18 | 0.792 | 0.6873 | 0.4669 | 0.088* | |
C13 | 0.6960 (2) | 1.0475 (2) | 0.77119 (15) | 0.0733 (5) | |
H13 | 0.7348 | 1.1186 | 0.7585 | 0.088* | |
C30 | 0.1947 (2) | 0.3142 (2) | 0.79299 (17) | 0.0824 (5) | |
H30 | 0.225 | 0.2156 | 0.802 | 0.099* | |
C9 | 0.1865 (2) | 0.6493 (2) | 0.97282 (12) | 0.0727 (5) | |
H9 | 0.1334 | 0.5931 | 0.9748 | 0.087* | |
C7 | 0.2225 (3) | 0.8226 (3) | 1.02838 (15) | 0.0930 (6) | |
H7 | 0.1924 | 0.8838 | 1.0667 | 0.112* | |
C12 | 0.7723 (2) | 0.9049 (2) | 0.83637 (18) | 0.0869 (6) | |
H12 | 0.8646 | 0.8785 | 0.867 | 0.104* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si | 0.0453 (2) | 0.03789 (19) | 0.0459 (2) | −0.01026 (14) | 0.00127 (14) | −0.01339 (15) |
C22 | 0.0462 (7) | 0.0397 (6) | 0.0490 (7) | −0.0149 (5) | 0.0004 (5) | −0.0130 (5) |
C27 | 0.0520 (8) | 0.0495 (7) | 0.0523 (8) | −0.0120 (6) | 0.0039 (6) | −0.0132 (6) |
C16 | 0.0445 (7) | 0.0428 (7) | 0.0528 (7) | −0.0119 (5) | 0.0008 (5) | −0.0173 (6) |
C23 | 0.0577 (8) | 0.0456 (7) | 0.0508 (7) | −0.0173 (6) | 0.0006 (6) | −0.0160 (6) |
C24 | 0.0740 (10) | 0.0521 (8) | 0.0490 (8) | −0.0209 (7) | −0.0066 (7) | −0.0071 (6) |
C28 | 0.0589 (8) | 0.0478 (7) | 0.0495 (7) | −0.0209 (6) | 0.0080 (6) | −0.0083 (6) |
C33 | 0.0634 (9) | 0.0542 (8) | 0.0664 (10) | −0.0218 (7) | 0.0009 (7) | −0.0094 (7) |
C5 | 0.0621 (8) | 0.0528 (8) | 0.0394 (7) | −0.0102 (7) | −0.0067 (6) | −0.0103 (6) |
C10 | 0.0553 (8) | 0.0491 (7) | 0.0534 (8) | −0.0125 (6) | −0.0025 (6) | −0.0231 (6) |
C21 | 0.0721 (10) | 0.0463 (8) | 0.0734 (10) | −0.0240 (7) | 0.0204 (8) | −0.0245 (7) |
C26 | 0.0496 (8) | 0.0469 (8) | 0.0709 (10) | −0.0087 (6) | 0.0039 (7) | −0.0169 (7) |
C4 | 0.0621 (8) | 0.0489 (7) | 0.0380 (7) | −0.0109 (6) | −0.0014 (6) | −0.0033 (6) |
C17 | 0.0601 (9) | 0.0571 (8) | 0.0800 (11) | −0.0285 (7) | 0.0159 (7) | −0.0325 (8) |
C15 | 0.0613 (9) | 0.0514 (8) | 0.0739 (10) | −0.0149 (7) | −0.0124 (7) | −0.0207 (7) |
C19 | 0.0688 (10) | 0.0645 (10) | 0.0729 (11) | −0.0131 (8) | 0.0205 (8) | −0.0311 (8) |
C1 | 0.0531 (8) | 0.0428 (7) | 0.0522 (8) | −0.0072 (6) | −0.0077 (6) | −0.0139 (6) |
C11 | 0.0662 (10) | 0.0605 (9) | 0.0825 (12) | −0.0148 (8) | −0.0191 (9) | −0.0186 (9) |
C14 | 0.0777 (11) | 0.0515 (8) | 0.0735 (10) | −0.0219 (8) | −0.0017 (8) | −0.0243 (8) |
C25 | 0.0596 (9) | 0.0432 (7) | 0.0673 (10) | −0.0107 (6) | −0.0102 (7) | −0.0048 (7) |
C32 | 0.0652 (10) | 0.0791 (12) | 0.0695 (10) | −0.0348 (9) | 0.0038 (8) | −0.0119 (9) |
C3 | 0.0532 (8) | 0.0402 (7) | 0.0506 (7) | −0.0106 (6) | −0.0010 (6) | −0.0067 (6) |
C6 | 0.0884 (12) | 0.0791 (11) | 0.0508 (9) | −0.0220 (9) | −0.0030 (8) | −0.0287 (8) |
C29 | 0.0684 (10) | 0.0523 (8) | 0.0768 (11) | −0.0241 (8) | 0.0115 (8) | −0.0163 (8) |
C20 | 0.0919 (13) | 0.0531 (9) | 0.0872 (12) | −0.0236 (9) | 0.0245 (10) | −0.0376 (9) |
C8 | 0.0977 (15) | 0.1110 (16) | 0.0519 (10) | −0.0323 (13) | 0.0255 (10) | −0.0292 (10) |
C31 | 0.0863 (13) | 0.0937 (14) | 0.0761 (12) | −0.0587 (12) | 0.0197 (10) | −0.0279 (10) |
C18 | 0.0650 (10) | 0.0756 (11) | 0.0819 (12) | −0.0335 (9) | 0.0257 (9) | −0.0316 (9) |
C13 | 0.0786 (11) | 0.0726 (11) | 0.0808 (12) | −0.0364 (9) | 0.0038 (9) | −0.0339 (9) |
C30 | 0.0940 (14) | 0.0662 (11) | 0.0966 (14) | −0.0450 (10) | 0.0232 (11) | −0.0300 (10) |
C9 | 0.0802 (11) | 0.0723 (10) | 0.0468 (8) | −0.0263 (9) | 0.0101 (8) | −0.0080 (7) |
C7 | 0.1103 (16) | 0.1108 (17) | 0.0582 (11) | −0.0319 (14) | 0.0175 (10) | −0.0462 (11) |
C12 | 0.0707 (11) | 0.0850 (13) | 0.1071 (16) | −0.0319 (10) | −0.0177 (11) | −0.0311 (12) |
Si—C16 | 1.8611 (15) | C17—H17 | 0.93 |
Si—C22 | 1.8777 (15) | C15—C14 | 1.383 (2) |
Si—C1 | 1.9007 (15) | C15—H15 | 0.93 |
Si—C3 | 1.9038 (15) | C19—C20 | 1.364 (3) |
C22—C23 | 1.3938 (19) | C19—C18 | 1.372 (2) |
C22—C27 | 1.404 (2) | C19—H19 | 0.93 |
C27—C26 | 1.378 (2) | C1—H1 | 0.98 |
C27—H27 | 0.93 | C11—C12 | 1.386 (3) |
C16—C21 | 1.389 (2) | C11—H11 | 0.93 |
C16—C17 | 1.393 (2) | C14—C13 | 1.366 (2) |
C23—C24 | 1.384 (2) | C14—H14 | 0.93 |
C23—H23 | 0.93 | C25—H25 | 0.93 |
C24—C25 | 1.372 (2) | C32—C31 | 1.373 (3) |
C24—H24 | 0.93 | C32—H32 | 0.93 |
C28—C29 | 1.392 (2) | C3—H3 | 0.98 |
C28—C33 | 1.395 (2) | C6—C7 | 1.388 (3) |
C28—C3 | 1.504 (2) | C6—H6 | 0.93 |
C33—C32 | 1.383 (2) | C29—C30 | 1.384 (3) |
C33—H33 | 0.93 | C29—H29 | 0.93 |
C5—C6 | 1.392 (2) | C20—H20C | 0.93 |
C5—C4 | 1.406 (2) | C8—C7 | 1.370 (3) |
C5—C1 | 1.520 (2) | C8—C9 | 1.386 (3) |
C10—C11 | 1.387 (2) | C8—H8 | 0.93 |
C10—C15 | 1.391 (2) | C31—C30 | 1.374 (3) |
C10—C1 | 1.507 (2) | C31—H31 | 0.93 |
C21—C20 | 1.381 (2) | C18—H18 | 0.93 |
C21—H21 | 0.93 | C13—C12 | 1.363 (3) |
C26—C25 | 1.379 (2) | C13—H13 | 0.93 |
C26—H26 | 0.93 | C30—H30 | 0.93 |
C4—C9 | 1.390 (2) | C9—H9 | 0.93 |
C4—C3 | 1.528 (2) | C7—H7 | 0.93 |
C17—C18 | 1.380 (2) | C12—H12 | 0.93 |
C16—Si—C22 | 109.70 (6) | C10—C1—H1 | 105.9 |
C16—Si—C1 | 115.01 (7) | C5—C1—H1 | 105.9 |
C22—Si—C1 | 111.95 (6) | Si—C1—H1 | 105.9 |
C16—Si—C3 | 115.92 (7) | C12—C11—C10 | 121.27 (16) |
C22—Si—C3 | 112.55 (6) | C12—C11—H11 | 119.4 |
C1—Si—C3 | 90.68 (7) | C10—C11—H11 | 119.4 |
C23—C22—C27 | 116.69 (12) | C13—C14—C15 | 120.22 (16) |
C23—C22—Si | 120.54 (10) | C13—C14—H14 | 119.9 |
C27—C22—Si | 122.74 (10) | C15—C14—H14 | 119.9 |
C26—C27—C22 | 121.44 (14) | C24—C25—C26 | 119.82 (14) |
C26—C27—H27 | 119.3 | C24—C25—H25 | 120.1 |
C22—C27—H27 | 119.3 | C26—C25—H25 | 120.1 |
C21—C16—C17 | 116.86 (13) | C31—C32—C33 | 120.45 (18) |
C21—C16—Si | 122.66 (11) | C31—C32—H32 | 119.8 |
C17—C16—Si | 120.40 (11) | C33—C32—H32 | 119.8 |
C24—C23—C22 | 121.81 (14) | C28—C3—C4 | 117.49 (13) |
C24—C23—H23 | 119.1 | C28—C3—Si | 120.72 (10) |
C22—C23—H23 | 119.1 | C4—C3—Si | 98.12 (9) |
C25—C24—C23 | 120.00 (14) | C28—C3—H3 | 106.4 |
C25—C24—H24 | 120 | C4—C3—H3 | 106.4 |
C23—C24—H24 | 120 | Si—C3—H3 | 106.4 |
C29—C28—C33 | 117.05 (16) | C7—C6—C5 | 119.5 (2) |
C29—C28—C3 | 120.66 (14) | C7—C6—H6 | 120.2 |
C33—C28—C3 | 122.28 (14) | C5—C6—H6 | 120.2 |
C32—C33—C28 | 121.30 (16) | C30—C29—C28 | 121.43 (17) |
C32—C33—H33 | 119.4 | C30—C29—H29 | 119.3 |
C28—C33—H33 | 119.4 | C28—C29—H29 | 119.3 |
C6—C5—C4 | 119.79 (16) | C19—C20—C21 | 120.38 (16) |
C6—C5—C1 | 124.81 (16) | C19—C20—H20C | 119.8 |
C4—C5—C1 | 115.26 (13) | C21—C20—H20C | 119.8 |
C11—C10—C15 | 116.65 (15) | C7—C8—C9 | 120.65 (19) |
C11—C10—C1 | 120.53 (14) | C7—C8—H8 | 119.7 |
C15—C10—C1 | 122.82 (13) | C9—C8—H8 | 119.7 |
C20—C21—C16 | 121.40 (15) | C32—C31—C30 | 119.43 (18) |
C20—C21—H21 | 119.3 | C32—C31—H31 | 120.3 |
C16—C21—H21 | 119.3 | C30—C31—H31 | 120.3 |
C27—C26—C25 | 120.24 (14) | C19—C18—C17 | 119.97 (16) |
C27—C26—H26 | 119.9 | C19—C18—H18 | 120 |
C25—C26—H26 | 119.9 | C17—C18—H18 | 120 |
C9—C4—C5 | 119.66 (16) | C12—C13—C14 | 119.35 (17) |
C9—C4—C3 | 124.98 (16) | C12—C13—H13 | 120.3 |
C5—C4—C3 | 115.24 (13) | C14—C13—H13 | 120.3 |
C18—C17—C16 | 121.58 (15) | C31—C30—C29 | 120.33 (18) |
C18—C17—H17 | 119.2 | C31—C30—H30 | 119.8 |
C16—C17—H17 | 119.2 | C29—C30—H30 | 119.8 |
C14—C15—C10 | 121.75 (15) | C8—C9—C4 | 119.7 (2) |
C14—C15—H15 | 119.1 | C8—C9—H9 | 120.2 |
C10—C15—H15 | 119.1 | C4—C9—H9 | 120.2 |
C20—C19—C18 | 119.79 (16) | C8—C7—C6 | 120.68 (19) |
C20—C19—H19 | 120.1 | C8—C7—H7 | 119.7 |
C18—C19—H19 | 120.1 | C6—C7—H7 | 119.7 |
C10—C1—C5 | 116.53 (12) | C13—C12—C11 | 120.75 (17) |
C10—C1—Si | 122.88 (10) | C13—C12—H12 | 119.6 |
C5—C1—Si | 98.27 (10) | C11—C12—H12 | 119.6 |