Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106000023/sq3001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106000023/sq3001Isup2.hkl |
CCDC reference: 299643
The crude product of the synthesis (Sui & Glaser, 2006) was purified by crystallization induced by slow diffusion of hexanes into an ethyl acetate solution. Single crystals suitable for X-ray analysis were grown by repeated recrystallization at room temperature.
H atoms were placed at calculated positions and included in the refinement using a riding model.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CIFTAB in SHELXL97.
C38H32 | F(000) = 1040 |
Mr = 488.64 | Dx = 1.198 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 6938 reflections |
a = 16.7069 (7) Å | θ = 2.5–27.1° |
b = 7.8826 (3) Å | µ = 0.07 mm−1 |
c = 21.2218 (8) Å | T = 173 K |
β = 104.129 (1)° | Prism, colorless |
V = 2710.23 (18) Å3 | 0.35 × 0.35 × 0.25 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 5965 independent reflections |
Radiation source: fine-focus sealed tube | 4592 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 27.1°, θmin = 1.4° |
Absorption correction: multi-scan (Blessing, 1996) | h = −21→21 |
Tmin = 0.92, Tmax = 0.98 | k = −10→10 |
18791 measured reflections | l = −27→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.6288P] where P = (Fo2 + 2Fc2)/3 |
5965 reflections | (Δ/σ)max < 0.001 |
345 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C38H32 | V = 2710.23 (18) Å3 |
Mr = 488.64 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 16.7069 (7) Å | µ = 0.07 mm−1 |
b = 7.8826 (3) Å | T = 173 K |
c = 21.2218 (8) Å | 0.35 × 0.35 × 0.25 mm |
β = 104.129 (1)° |
Bruker SMART CCD area-detector diffractometer | 5965 independent reflections |
Absorption correction: multi-scan (Blessing, 1996) | 4592 reflections with I > 2σ(I) |
Tmin = 0.92, Tmax = 0.98 | Rint = 0.030 |
18791 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
5965 reflections | Δρmin = −0.15 e Å−3 |
345 parameters |
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 | 0.22531 (7) | 0.47276 (16) | 0.14738 (6) | 0.0251 (3) | |
C2 | 0.16964 (7) | 0.62448 (16) | 0.15015 (6) | 0.0253 (3) | |
C3 | 0.18496 (8) | 0.77633 (16) | 0.11942 (6) | 0.0266 (3) | |
C4 | 0.25732 (8) | 0.78667 (17) | 0.09249 (7) | 0.0294 (3) | |
H4 | 0.2599 | 0.8734 | 0.0619 | 0.035* | |
C5 | 0.32049 (8) | 0.67671 (17) | 0.10976 (6) | 0.0276 (3) | |
C6 | 0.31366 (8) | 0.54349 (17) | 0.15962 (6) | 0.0282 (3) | |
H6A | 0.3296 | 0.5940 | 0.2036 | 0.034* | |
H6B | 0.3524 | 0.4495 | 0.1579 | 0.034* | |
C7 | 0.10500 (8) | 0.62126 (17) | 0.18047 (6) | 0.0266 (3) | |
H7 | 0.0946 | 0.5192 | 0.2009 | 0.032* | |
C8 | 0.05423 (8) | 0.76219 (17) | 0.18231 (6) | 0.0260 (3) | |
C9 | 0.06573 (8) | 0.90904 (16) | 0.14728 (6) | 0.0264 (3) | |
C10 | 0.13100 (8) | 0.91225 (17) | 0.11670 (6) | 0.0283 (3) | |
H10 | 0.1388 | 1.0109 | 0.0932 | 0.034* | |
C11 | 0.20047 (8) | 0.38731 (16) | 0.07999 (6) | 0.0261 (3) | |
C12 | 0.25787 (9) | 0.3024 (2) | 0.05407 (7) | 0.0389 (4) | |
H12 | 0.3141 | 0.3013 | 0.0775 | 0.047* | |
C13 | 0.23506 (10) | 0.2191 (2) | −0.00514 (8) | 0.0461 (4) | |
H13 | 0.2755 | 0.1613 | −0.0217 | 0.055* | |
C14 | 0.15370 (10) | 0.2200 (2) | −0.04007 (7) | 0.0432 (4) | |
H14 | 0.1380 | 0.1646 | −0.0810 | 0.052* | |
C15 | 0.09551 (10) | 0.30212 (19) | −0.01494 (7) | 0.0413 (4) | |
H15 | 0.0393 | 0.3023 | −0.0384 | 0.050* | |
C16 | 0.11875 (8) | 0.38436 (18) | 0.04440 (7) | 0.0338 (3) | |
H16 | 0.0779 | 0.4400 | 0.0612 | 0.041* | |
C17 | 0.22143 (8) | 0.33882 (18) | 0.19915 (7) | 0.0306 (3) | |
H17A | 0.2367 | 0.3910 | 0.2423 | 0.046* | |
H17B | 0.2599 | 0.2464 | 0.1969 | 0.046* | |
H17C | 0.1652 | 0.2936 | 0.1912 | 0.046* | |
C18 | 0.39515 (8) | 0.68333 (17) | 0.08358 (7) | 0.0303 (3) | |
C19 | 0.46815 (8) | 0.60006 (19) | 0.11420 (7) | 0.0357 (3) | |
H19 | 0.4703 | 0.5374 | 0.1528 | 0.043* | |
C20 | 0.53780 (9) | 0.6070 (2) | 0.08933 (8) | 0.0413 (4) | |
H20 | 0.5868 | 0.5500 | 0.1112 | 0.050* | |
C21 | 0.53595 (10) | 0.6961 (2) | 0.03322 (8) | 0.0444 (4) | |
H21 | 0.5835 | 0.7011 | 0.0162 | 0.053* | |
C22 | 0.46440 (10) | 0.7780 (2) | 0.00191 (9) | 0.0473 (4) | |
H22 | 0.4628 | 0.8396 | −0.0368 | 0.057* | |
C23 | 0.39489 (10) | 0.7713 (2) | 0.02630 (8) | 0.0409 (4) | |
H23 | 0.3460 | 0.8276 | 0.0037 | 0.049* | |
C24 | −0.01344 (8) | 0.74966 (16) | 0.21561 (6) | 0.0270 (3) | |
H24 | −0.0638 | 0.8030 | 0.1945 | 0.032* | |
C25 | −0.01255 (8) | 0.67198 (17) | 0.27222 (6) | 0.0274 (3) | |
C26 | −0.08955 (8) | 0.66035 (18) | 0.29558 (6) | 0.0291 (3) | |
C27 | −0.10207 (8) | 0.52268 (19) | 0.33339 (7) | 0.0335 (3) | |
H27 | −0.0602 | 0.4390 | 0.3456 | 0.040* | |
C28 | −0.17476 (9) | 0.5060 (2) | 0.35351 (8) | 0.0414 (4) | |
H28 | −0.1827 | 0.4099 | 0.3783 | 0.050* | |
C29 | −0.23536 (10) | 0.6275 (2) | 0.33788 (8) | 0.0466 (4) | |
H29 | −0.2849 | 0.6159 | 0.3519 | 0.056* | |
C30 | −0.22347 (10) | 0.7665 (2) | 0.30158 (9) | 0.0509 (4) | |
H30 | −0.2649 | 0.8515 | 0.2910 | 0.061* | |
C31 | −0.15167 (9) | 0.7828 (2) | 0.28053 (8) | 0.0416 (4) | |
H31 | −0.1446 | 0.8789 | 0.2554 | 0.050* | |
C32 | 0.06290 (8) | 0.5901 (2) | 0.31534 (7) | 0.0356 (3) | |
H32A | 0.0601 | 0.4670 | 0.3088 | 0.053* | |
H32B | 0.0650 | 0.6157 | 0.3609 | 0.053* | |
H32C | 0.1126 | 0.6346 | 0.3044 | 0.053* | |
C33 | 0.01057 (8) | 1.05973 (16) | 0.14203 (6) | 0.0262 (3) | |
C34 | −0.00444 (8) | 1.13959 (18) | 0.19661 (7) | 0.0314 (3) | |
H34 | 0.0202 | 1.0963 | 0.2386 | 0.038* | |
C35 | −0.05489 (9) | 1.28145 (18) | 0.19036 (8) | 0.0357 (3) | |
H35 | −0.0643 | 1.3345 | 0.2281 | 0.043* | |
C36 | −0.09152 (9) | 1.34600 (18) | 0.12986 (8) | 0.0382 (3) | |
H36 | −0.1255 | 1.4440 | 0.1258 | 0.046* | |
C37 | −0.07847 (10) | 1.26711 (19) | 0.07521 (8) | 0.0405 (4) | |
H37 | −0.1044 | 1.3096 | 0.0333 | 0.049* | |
C38 | −0.02762 (9) | 1.12580 (18) | 0.08134 (7) | 0.0343 (3) | |
H38 | −0.0187 | 1.0732 | 0.0434 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0247 (6) | 0.0256 (7) | 0.0256 (7) | −0.0011 (5) | 0.0074 (5) | 0.0015 (5) |
C2 | 0.0258 (6) | 0.0259 (7) | 0.0237 (6) | −0.0021 (5) | 0.0049 (5) | −0.0012 (5) |
C3 | 0.0291 (6) | 0.0263 (7) | 0.0251 (7) | −0.0019 (5) | 0.0081 (5) | −0.0014 (5) |
C4 | 0.0345 (7) | 0.0265 (7) | 0.0301 (7) | −0.0045 (6) | 0.0137 (6) | 0.0008 (6) |
C5 | 0.0279 (6) | 0.0284 (7) | 0.0277 (7) | −0.0063 (5) | 0.0094 (5) | −0.0051 (5) |
C6 | 0.0249 (6) | 0.0321 (7) | 0.0275 (7) | −0.0009 (5) | 0.0063 (5) | −0.0022 (6) |
C7 | 0.0285 (6) | 0.0255 (7) | 0.0261 (7) | −0.0024 (5) | 0.0072 (5) | 0.0028 (5) |
C8 | 0.0250 (6) | 0.0285 (7) | 0.0244 (6) | −0.0018 (5) | 0.0059 (5) | 0.0005 (5) |
C9 | 0.0279 (6) | 0.0261 (7) | 0.0250 (6) | −0.0011 (5) | 0.0062 (5) | −0.0016 (5) |
C10 | 0.0329 (7) | 0.0250 (7) | 0.0282 (7) | −0.0031 (6) | 0.0100 (6) | 0.0017 (5) |
C11 | 0.0294 (6) | 0.0230 (7) | 0.0264 (7) | −0.0033 (5) | 0.0076 (5) | 0.0029 (5) |
C12 | 0.0324 (7) | 0.0491 (9) | 0.0363 (8) | −0.0037 (7) | 0.0107 (6) | −0.0099 (7) |
C13 | 0.0494 (9) | 0.0529 (10) | 0.0419 (9) | −0.0083 (8) | 0.0222 (8) | −0.0138 (8) |
C14 | 0.0597 (10) | 0.0401 (9) | 0.0282 (8) | −0.0153 (8) | 0.0078 (7) | −0.0052 (7) |
C15 | 0.0431 (8) | 0.0350 (8) | 0.0381 (8) | −0.0049 (7) | −0.0052 (7) | −0.0008 (7) |
C16 | 0.0333 (7) | 0.0273 (7) | 0.0380 (8) | 0.0004 (6) | 0.0031 (6) | −0.0006 (6) |
C17 | 0.0307 (7) | 0.0310 (7) | 0.0308 (7) | 0.0033 (6) | 0.0091 (6) | 0.0061 (6) |
C18 | 0.0305 (7) | 0.0286 (7) | 0.0339 (7) | −0.0066 (6) | 0.0119 (6) | −0.0074 (6) |
C19 | 0.0322 (7) | 0.0430 (9) | 0.0334 (8) | −0.0044 (6) | 0.0107 (6) | −0.0056 (6) |
C20 | 0.0301 (7) | 0.0507 (10) | 0.0443 (9) | −0.0026 (7) | 0.0117 (7) | −0.0118 (7) |
C21 | 0.0378 (8) | 0.0495 (10) | 0.0537 (10) | −0.0100 (7) | 0.0265 (7) | −0.0113 (8) |
C22 | 0.0516 (9) | 0.0478 (10) | 0.0515 (10) | −0.0035 (8) | 0.0299 (8) | 0.0042 (8) |
C23 | 0.0404 (8) | 0.0405 (9) | 0.0462 (9) | 0.0015 (7) | 0.0192 (7) | 0.0052 (7) |
C24 | 0.0252 (6) | 0.0254 (7) | 0.0312 (7) | 0.0009 (5) | 0.0083 (5) | 0.0020 (5) |
C25 | 0.0264 (6) | 0.0265 (7) | 0.0299 (7) | −0.0008 (5) | 0.0078 (5) | −0.0009 (5) |
C26 | 0.0291 (6) | 0.0320 (7) | 0.0276 (7) | −0.0003 (6) | 0.0092 (5) | −0.0006 (6) |
C27 | 0.0342 (7) | 0.0364 (8) | 0.0326 (8) | 0.0027 (6) | 0.0131 (6) | 0.0040 (6) |
C28 | 0.0421 (8) | 0.0465 (9) | 0.0409 (9) | −0.0031 (7) | 0.0205 (7) | 0.0071 (7) |
C29 | 0.0351 (8) | 0.0600 (11) | 0.0521 (10) | 0.0023 (8) | 0.0248 (7) | 0.0050 (8) |
C30 | 0.0392 (8) | 0.0570 (11) | 0.0629 (11) | 0.0169 (8) | 0.0251 (8) | 0.0149 (9) |
C31 | 0.0394 (8) | 0.0410 (9) | 0.0495 (9) | 0.0079 (7) | 0.0207 (7) | 0.0124 (7) |
C32 | 0.0279 (7) | 0.0464 (9) | 0.0326 (8) | 0.0003 (6) | 0.0074 (6) | 0.0077 (7) |
C33 | 0.0260 (6) | 0.0238 (7) | 0.0301 (7) | −0.0041 (5) | 0.0092 (5) | 0.0006 (5) |
C34 | 0.0290 (7) | 0.0345 (8) | 0.0306 (7) | −0.0014 (6) | 0.0072 (6) | −0.0014 (6) |
C35 | 0.0333 (7) | 0.0334 (8) | 0.0442 (9) | −0.0017 (6) | 0.0169 (6) | −0.0082 (7) |
C36 | 0.0346 (7) | 0.0254 (7) | 0.0570 (10) | 0.0027 (6) | 0.0155 (7) | 0.0032 (7) |
C37 | 0.0469 (9) | 0.0333 (8) | 0.0404 (9) | 0.0037 (7) | 0.0091 (7) | 0.0114 (7) |
C38 | 0.0455 (8) | 0.0291 (7) | 0.0300 (7) | 0.0011 (6) | 0.0128 (6) | 0.0022 (6) |
C1—C2 | 1.5250 (18) | C19—H19 | 0.9500 |
C1—C17 | 1.5365 (18) | C20—C21 | 1.376 (2) |
C1—C6 | 1.5395 (17) | C20—H20 | 0.9500 |
C1—C11 | 1.5432 (18) | C21—C22 | 1.378 (2) |
C2—C7 | 1.3856 (17) | C21—H21 | 0.9500 |
C2—C3 | 1.4160 (18) | C22—C23 | 1.383 (2) |
C3—C10 | 1.3923 (18) | C22—H22 | 0.9500 |
C3—C4 | 1.4602 (18) | C23—H23 | 0.9500 |
C4—C5 | 1.3455 (19) | C24—C25 | 1.3453 (18) |
C4—H4 | 0.9500 | C24—H24 | 0.9500 |
C5—C18 | 1.4851 (18) | C25—C26 | 1.4902 (18) |
C5—C6 | 1.5148 (19) | C25—C32 | 1.5098 (18) |
C6—H6A | 0.9900 | C26—C27 | 1.3954 (19) |
C6—H6B | 0.9900 | C26—C31 | 1.396 (2) |
C7—C8 | 1.4040 (18) | C27—C28 | 1.3884 (19) |
C7—H7 | 0.9500 | C27—H27 | 0.9500 |
C8—C9 | 1.4139 (18) | C28—C29 | 1.374 (2) |
C8—C24 | 1.4755 (17) | C28—H28 | 0.9500 |
C9—C10 | 1.3987 (18) | C29—C30 | 1.381 (2) |
C9—C33 | 1.4908 (18) | C29—H29 | 0.9500 |
C10—H10 | 0.9500 | C30—C31 | 1.384 (2) |
C11—C12 | 1.3885 (19) | C30—H30 | 0.9500 |
C11—C16 | 1.3898 (18) | C31—H31 | 0.9500 |
C12—C13 | 1.386 (2) | C32—H32A | 0.9800 |
C12—H12 | 0.9500 | C32—H32B | 0.9800 |
C13—C14 | 1.380 (2) | C32—H32C | 0.9800 |
C13—H13 | 0.9500 | C33—C38 | 1.3914 (19) |
C14—C15 | 1.379 (2) | C33—C34 | 1.3938 (18) |
C14—H14 | 0.9500 | C34—C35 | 1.387 (2) |
C15—C16 | 1.385 (2) | C34—H34 | 0.9500 |
C15—H15 | 0.9500 | C35—C36 | 1.378 (2) |
C16—H16 | 0.9500 | C35—H35 | 0.9500 |
C17—H17A | 0.9800 | C36—C37 | 1.379 (2) |
C17—H17B | 0.9800 | C36—H36 | 0.9500 |
C17—H17C | 0.9800 | C37—C38 | 1.388 (2) |
C18—C19 | 1.398 (2) | C37—H37 | 0.9500 |
C18—C23 | 1.398 (2) | C38—H38 | 0.9500 |
C19—C20 | 1.3912 (19) | ||
C2—C1—C17 | 112.26 (10) | C20—C19—C18 | 121.39 (14) |
C2—C1—C6 | 106.15 (10) | C20—C19—H19 | 119.3 |
C17—C1—C6 | 109.52 (10) | C18—C19—H19 | 119.3 |
C2—C1—C11 | 110.46 (10) | C21—C20—C19 | 120.27 (15) |
C17—C1—C11 | 108.30 (11) | C21—C20—H20 | 119.9 |
C6—C1—C11 | 110.14 (10) | C19—C20—H20 | 119.9 |
C7—C2—C3 | 118.58 (12) | C20—C21—C22 | 119.32 (14) |
C7—C2—C1 | 123.73 (11) | C20—C21—H21 | 120.3 |
C3—C2—C1 | 117.69 (11) | C22—C21—H21 | 120.3 |
C10—C3—C2 | 118.79 (12) | C21—C22—C23 | 120.70 (16) |
C10—C3—C4 | 122.03 (12) | C21—C22—H22 | 119.6 |
C2—C3—C4 | 119.17 (12) | C23—C22—H22 | 119.7 |
C5—C4—C3 | 121.78 (12) | C22—C23—C18 | 121.30 (15) |
C5—C4—H4 | 119.1 | C22—C23—H23 | 119.3 |
C3—C4—H4 | 119.1 | C18—C23—H23 | 119.4 |
C4—C5—C18 | 123.37 (13) | C25—C24—C8 | 127.98 (12) |
C4—C5—C6 | 116.68 (11) | C25—C24—H24 | 116.0 |
C18—C5—C6 | 119.94 (12) | C8—C24—H24 | 116.0 |
C5—C6—C1 | 111.45 (10) | C24—C25—C26 | 120.19 (12) |
C5—C6—H6A | 109.3 | C24—C25—C32 | 124.15 (12) |
C1—C6—H6A | 109.3 | C26—C25—C32 | 115.65 (11) |
C5—C6—H6B | 109.3 | C27—C26—C31 | 117.51 (12) |
C1—C6—H6B | 109.3 | C27—C26—C25 | 120.12 (12) |
H6A—C6—H6B | 108.0 | C31—C26—C25 | 122.37 (12) |
C2—C7—C8 | 122.89 (12) | C28—C27—C26 | 121.02 (13) |
C2—C7—H7 | 118.6 | C28—C27—H27 | 119.5 |
C8—C7—H7 | 118.6 | C26—C27—H27 | 119.5 |
C7—C8—C9 | 118.20 (11) | C29—C28—C27 | 120.56 (14) |
C7—C8—C24 | 119.94 (12) | C29—C28—H28 | 119.7 |
C9—C8—C24 | 121.66 (11) | C27—C28—H28 | 119.7 |
C10—C9—C8 | 118.69 (12) | C28—C29—C30 | 119.31 (14) |
C10—C9—C33 | 119.25 (12) | C28—C29—H29 | 120.3 |
C8—C9—C33 | 122.06 (11) | C30—C29—H29 | 120.3 |
C3—C10—C9 | 122.49 (12) | C29—C30—C31 | 120.49 (15) |
C3—C10—H10 | 118.8 | C29—C30—H30 | 119.8 |
C9—C10—H10 | 118.8 | C31—C30—H30 | 119.8 |
C12—C11—C16 | 117.30 (12) | C30—C31—C26 | 121.09 (14) |
C12—C11—C1 | 121.47 (11) | C30—C31—H31 | 119.5 |
C16—C11—C1 | 121.14 (12) | C26—C31—H31 | 119.5 |
C13—C12—C11 | 121.59 (14) | C25—C32—H32A | 109.5 |
C13—C12—H12 | 119.2 | C25—C32—H32B | 109.5 |
C11—C12—H12 | 119.2 | H32A—C32—H32B | 109.5 |
C14—C13—C12 | 120.07 (15) | C25—C32—H32C | 109.5 |
C14—C13—H13 | 120.0 | H32A—C32—H32C | 109.5 |
C12—C13—H13 | 120.0 | H32B—C32—H32C | 109.5 |
C15—C14—C13 | 119.31 (14) | C38—C33—C34 | 117.73 (12) |
C15—C14—H14 | 120.3 | C38—C33—C9 | 120.19 (12) |
C13—C14—H14 | 120.3 | C34—C33—C9 | 122.08 (12) |
C14—C15—C16 | 120.25 (14) | C35—C34—C33 | 120.87 (13) |
C14—C15—H15 | 119.9 | C35—C34—H34 | 119.6 |
C16—C15—H15 | 119.9 | C33—C34—H34 | 119.6 |
C15—C16—C11 | 121.47 (14) | C36—C35—C34 | 120.54 (14) |
C15—C16—H16 | 119.3 | C36—C35—H35 | 119.7 |
C11—C16—H16 | 119.3 | C34—C35—H35 | 119.7 |
C1—C17—H17A | 109.5 | C35—C36—C37 | 119.45 (14) |
C1—C17—H17B | 109.5 | C35—C36—H36 | 120.3 |
H17A—C17—H17B | 109.5 | C37—C36—H36 | 120.3 |
C1—C17—H17C | 109.5 | C36—C37—C38 | 120.12 (14) |
H17A—C17—H17C | 109.5 | C36—C37—H37 | 119.9 |
H17B—C17—H17C | 109.5 | C38—C37—H37 | 119.9 |
C19—C18—C23 | 117.01 (13) | C37—C38—C33 | 121.27 (14) |
C19—C18—C5 | 121.79 (13) | C37—C38—H38 | 119.4 |
C23—C18—C5 | 121.19 (13) | C33—C38—H38 | 119.4 |
C17—C1—C2—C7 | −18.80 (17) | C12—C11—C16—C15 | −0.9 (2) |
C6—C1—C2—C7 | −138.43 (12) | C1—C11—C16—C15 | −177.41 (13) |
C11—C1—C2—C7 | 102.18 (14) | C4—C5—C18—C19 | 162.43 (13) |
C17—C1—C2—C3 | 161.71 (11) | C6—C5—C18—C19 | −16.20 (19) |
C6—C1—C2—C3 | 42.08 (15) | C4—C5—C18—C23 | −18.7 (2) |
C11—C1—C2—C3 | −77.31 (14) | C6—C5—C18—C23 | 162.68 (13) |
C7—C2—C3—C10 | −4.64 (18) | C23—C18—C19—C20 | 1.1 (2) |
C1—C2—C3—C10 | 174.88 (11) | C5—C18—C19—C20 | −179.99 (13) |
C7—C2—C3—C4 | 174.43 (12) | C18—C19—C20—C21 | −0.4 (2) |
C1—C2—C3—C4 | −6.05 (17) | C19—C20—C21—C22 | −0.1 (2) |
C10—C3—C4—C5 | 161.77 (13) | C20—C21—C22—C23 | 0.0 (3) |
C2—C3—C4—C5 | −17.27 (19) | C21—C22—C23—C18 | 0.7 (3) |
C3—C4—C5—C18 | −179.85 (12) | C19—C18—C23—C22 | −1.2 (2) |
C3—C4—C5—C6 | −1.18 (19) | C5—C18—C23—C22 | 179.85 (14) |
C4—C5—C6—C1 | 40.45 (16) | C7—C8—C24—C25 | 40.7 (2) |
C18—C5—C6—C1 | −140.84 (12) | C9—C8—C24—C25 | −144.45 (14) |
C2—C1—C6—C5 | −58.45 (13) | C8—C24—C25—C26 | −174.88 (12) |
C17—C1—C6—C5 | −179.85 (11) | C8—C24—C25—C32 | 4.2 (2) |
C11—C1—C6—C5 | 61.14 (14) | C24—C25—C26—C27 | 149.57 (14) |
C3—C2—C7—C8 | −0.29 (19) | C32—C25—C26—C27 | −29.59 (18) |
C1—C2—C7—C8 | −179.77 (12) | C24—C25—C26—C31 | −29.8 (2) |
C2—C7—C8—C9 | 5.12 (19) | C32—C25—C26—C31 | 151.08 (14) |
C2—C7—C8—C24 | −179.89 (12) | C31—C26—C27—C28 | 1.9 (2) |
C7—C8—C9—C10 | −4.92 (18) | C25—C26—C27—C28 | −177.45 (13) |
C24—C8—C9—C10 | −179.82 (12) | C26—C27—C28—C29 | −1.6 (2) |
C7—C8—C9—C33 | 175.07 (12) | C27—C28—C29—C30 | 0.3 (3) |
C24—C8—C9—C33 | 0.17 (19) | C28—C29—C30—C31 | 0.7 (3) |
C2—C3—C10—C9 | 4.81 (19) | C29—C30—C31—C26 | −0.3 (3) |
C4—C3—C10—C9 | −174.23 (12) | C27—C26—C31—C30 | −1.0 (2) |
C8—C9—C10—C3 | 0.06 (19) | C25—C26—C31—C30 | 178.38 (15) |
C33—C9—C10—C3 | −179.94 (12) | C10—C9—C33—C38 | 53.49 (17) |
C2—C1—C11—C12 | 150.82 (13) | C8—C9—C33—C38 | −126.50 (14) |
C17—C1—C11—C12 | −85.87 (15) | C10—C9—C33—C34 | −126.21 (14) |
C6—C1—C11—C12 | 33.88 (17) | C8—C9—C33—C34 | 53.79 (18) |
C2—C1—C11—C16 | −32.79 (16) | C38—C33—C34—C35 | −0.87 (19) |
C17—C1—C11—C16 | 90.52 (14) | C9—C33—C34—C35 | 178.85 (12) |
C6—C1—C11—C16 | −149.73 (12) | C33—C34—C35—C36 | 0.3 (2) |
C16—C11—C12—C13 | 0.6 (2) | C34—C35—C36—C37 | 0.8 (2) |
C1—C11—C12—C13 | 177.09 (14) | C35—C36—C37—C38 | −1.2 (2) |
C11—C12—C13—C14 | 0.4 (2) | C36—C37—C38—C33 | 0.6 (2) |
C12—C13—C14—C15 | −1.0 (2) | C34—C33—C38—C37 | 0.5 (2) |
C13—C14—C15—C16 | 0.7 (2) | C9—C33—C38—C37 | −179.26 (13) |
C14—C15—C16—C11 | 0.2 (2) |
Experimental details
Crystal data | |
Chemical formula | C38H32 |
Mr | 488.64 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 16.7069 (7), 7.8826 (3), 21.2218 (8) |
β (°) | 104.129 (1) |
V (Å3) | 2710.23 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.35 × 0.35 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (Blessing, 1996) |
Tmin, Tmax | 0.92, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18791, 5965, 4592 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.642 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.114, 1.04 |
No. of reflections | 5965 |
No. of parameters | 345 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.15 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), CIFTAB in SHELXL97.
1,2-Dihydronaphthalenes (DHNs, dialin) (Autrey et al., 2003; Gorner et al., 2002; Laarhoven et al., 1985; Woning et al., 1991) and distyrylbenzenes (DSBs) (Bartholomew & Bazan, 2002; Hong et al., 2005; Lupton et al., 2002; Ma et al., 2002; Wang et al., 2003; Marri et al., 2005; Ni et al., 1999; Sarker et al., 2003; Xie et al., 2005) have been attracting increased attention recently because of their optical and optoelectronic properties, and more efficient syntheses of DHN (Maeda et al., 2002) and DSB (Wong et al., 1998) have been sought because of this interest in their properties. The C38H32 hydrocarbon (I), 1-methyl-1,3,6-triphenyl-7-(2-phenylpropenyl)-1,2- dihydronaphthalene, presents a novel framework that combines the functionalities of a bis-arene substituted DHN and of a substituted DSB.
We have relied on arene–arene interactions of diarenes (Ar–spacer–Ar') as lateral synthons (Lewis et al., 2001) in the design of polar crystals with layers of parallel beloamphiphiles (Glaser, Knotts & Wu, 2003; Glaser, 2006). We have explored 1,4-diphenylazines (Chen et al., 1995; Lewis et al., 2000a,b) 1,4-diphenylbutadienes (Glaser, Dendi et al., 2003) and biphenyls (Glaser et al., 2006). Facile torsion of the arenes along with conformational flexibility of the spacer (Glaser & Chen, 1998) allow for optimization of arene–arene interactions. Hydrocarbon (I) is a crossed bis-diarene with the ability to engage in arene–arene interactions in every direction and various types of arene–arene interactions cooperate in the formation of its lamellar crystal architecture.
We report here the single-crystal structure of (I) (Fig. 1). The systematic name of (I) stresses its `dihydronaphthalene' nature, and the DSB framework also is highlighted in the scheme above. A search of the Cambridge Structural Database (Allen, 2002) suggests that (I) is the first compound with a framework that combines the DSB and DHN moieties.
Distyrylbenzene prefers the E configuration at both double bonds so as to place the terminal arenes B and C far from the central arene A, and the same is true in (I). There is, however, a remarkable conformational difference. While DSB itself prefers the anti conformation with regard to the 1,4-exocyclic bonds of arene A (highlighted in bold in the first scheme below) (Wu et al., 2003), compound (I) crystallizes in the syn conformation. It is not clear whether this conformation is the result of intramolecular features (e.g. steric interference by arene E) or whether this conformation is adopted to improve intermolecular bonding in the crystal structure.
Molecule (I) has a chiral center at atom C1 and the crystal is a racemate (Jacques et al., 1981; Brock et al., 1991). As can be seen in Fig. 2, layers are formed by stacking pure R and S enantiomers in one layer direction and stacks of R and S enantiomers alternate in the second layer direction with double-stack alternation. In addition to the two neighbors with the same configuration in the stack, every molecule is surrounded by two S and two R enantiomers (and vice versa) in the neighboring stacks because of this double-stack alternation.
The stacking distance is very long (7.883 Å) and there are no direct stacking interactions. Instead, the stacks are held together by bridging interactions with molecules in the neighboring stacks. All of these intermolecular interactions involve arene–arene bonding, viz. pair interactions involving arenes B and C, and triple interactions involving arenes A, D and E. The long axes of the DSB units are more or less perpendicular to the layer surfaces. For a molecule with a given B-to-C direction, all of its next neighbors in neighboring stacks are oriented in the opposite direction (see Fig. 3). The homochiral double-stacks together with this alternation of the orientations results in the four-stack repeating unit {RCRBSCSB}. In contrast, the D-to-E direction is the same for all the molecules in every homochiral double stack and the D-to-E direction alternates between the homochiral double stacks. While the DSB units alternate within both the R and the S substructures, the homochiral substructures feature opposing polarity along the long axes of the DHN-based diarenes.