The title compounds, 3a,9a-
trans-9,9a-
trans-4,4-dimethyl-9-phenyl-2,3,3a,4,9,9a-hexahydrobenzo[
f]indene, C
21H
24, (I), and 3a,4-
trans-3a,9a-
cis-9,9a-
trans-4-methoxy-9-phenyl-2,3,3a,4,9,9a-hexahydrobenzo[
f]indene, C
20H
22O, (II), are products of the photoinduced electron-transfer reaction of 1,1-diphenyl-1,
n-alkadienes. The molecular structures are in good agreement with those proposed from the reaction mechanisms. The central rings of the fused systems of both compounds take chair and boat conformations in (I) and (II), respectively. There are no remarkable short contacts shorter than the sum of the van der Waals radii in the crystals, but some weak C—H
π interactions are found.
Supporting information
CCDC references: 147641; 147642
The syntheses of the title compounds have been reported previously by Ishii et al. (1998). Crystals of (I) and (II) were obtained from solutions in methanol.
All H atoms of (I) were located in difference maps and were refined as riding models, in which the distances of the C—H bonds were constrained to be 0.98, 0.97, 0.96 and 0.93 Å for the H atoms of methyne, methylene, methyl and aromatic moieties, respectively. The isotropic displacement parameters of the H atoms were constrained to be Uiso(H) = 1.5Ueq(C).
All H atoms of (II) were located in difference maps and were refined isotropically.
For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1993). Program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) for (I); SIR97 (Altomare et al., 1998) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SV (Nemoto & Ohashi, 1993); software used to prepare material for publication: SHELXL97.
(I) 3a,9a-
trans-9,9a-
trans-4,4-dimethyl-9- phenyl-2,3,3a,4,9,9a-hexahydrobenzo[
f]indene
top
Crystal data top
C21H24 | F(000) = 300 |
Mr = 276.40 | Dx = 1.119 Mg m−3 |
Triclinic, P1 | Melting point = 373–374 K |
a = 9.483 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.042 (2) Å | Cell parameters from 25 reflections |
c = 9.394 (2) Å | θ = 14–15° |
α = 104.14 (2)° | µ = 0.06 mm−1 |
β = 101.45 (2)° | T = 298 K |
γ = 114.03 (2)° | Block, colourless |
V = 820.4 (3) Å3 | 0.3 × 0.3 × 0.2 mm |
Z = 2 | |
Data collection top
Rigaku AFC-7R diffractometer | 2621 reflections with I > 2σ(I) |
Radiation source: normal-focus rotating anode | Rint = 0.019 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
ω/2θ scan | h = 0→12 |
Absorption correction: ψ-scan (North et al., 1968) | k = −14→13 |
Tmin = 0.920, Tmax = 0.987 | l = −12→11 |
4073 measured reflections | 3 standard reflections every 100 reflections |
3769 independent reflections | intensity decay: 0.4% |
Refinement top
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)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0726P)2 + 0.1178P] where P = (Fo2 + 2Fc2)/3 |
3769 reflections | (Δ/σ)max < 0.001 |
207 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C21H24 | γ = 114.03 (2)° |
Mr = 276.40 | V = 820.4 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.483 (2) Å | Mo Kα radiation |
b = 11.042 (2) Å | µ = 0.06 mm−1 |
c = 9.394 (2) Å | T = 298 K |
α = 104.14 (2)° | 0.3 × 0.3 × 0.2 mm |
β = 101.45 (2)° | |
Data collection top
Rigaku AFC-7R diffractometer | 2621 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (North et al., 1968) | Rint = 0.019 |
Tmin = 0.920, Tmax = 0.987 | 3 standard reflections every 100 reflections |
4073 measured reflections | intensity decay: 0.4% |
3769 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.18 e Å−3 |
3769 reflections | Δρmin = −0.21 e Å−3 |
207 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1897 (2) | 0.3213 (2) | 0.75371 (19) | 0.0679 | |
H11 | 0.2695 | 0.4207 | 0.8109 | 0.102* | |
H12 | 0.2037 | 0.2662 | 0.8161 | 0.102* | |
C2 | 0.0155 (3) | 0.3011 (3) | 0.7131 (3) | 0.0944 | |
H21 | 0.0134 | 0.3818 | 0.7808 | 0.142* | |
H22 | −0.0574 | 0.2156 | 0.7260 | 0.142* | |
C3 | −0.0388 (2) | 0.2886 (2) | 0.5434 (2) | 0.0723 | |
H31 | −0.0719 | 0.3596 | 0.5349 | 0.108* | |
H32 | −0.1301 | 0.1949 | 0.4794 | 0.108* | |
C3a | 0.11184 (17) | 0.31334 (15) | 0.49179 (17) | 0.0478 | |
H3a1 | 0.1779 | 0.4165 | 0.5223 | 0.072* | |
C4 | 0.08534 (17) | 0.24763 (16) | 0.31854 (17) | 0.0507 | |
C4a | 0.24778 (16) | 0.26046 (14) | 0.30064 (15) | 0.0436 | |
C5 | 0.2610 (2) | 0.23392 (18) | 0.15135 (17) | 0.0578 | |
H51 | 0.1718 | 0.2110 | 0.0674 | 0.087* | |
C6 | 0.4004 (2) | 0.24043 (19) | 0.12413 (19) | 0.0624 | |
H61 | 0.4049 | 0.2218 | 0.0235 | 0.094* | |
C7 | 0.5331 (2) | 0.27476 (17) | 0.24710 (19) | 0.0571 | |
H71 | 0.6288 | 0.2807 | 0.2304 | 0.086* | |
C8 | 0.52460 (17) | 0.30048 (15) | 0.39561 (17) | 0.0469 | |
H81 | 0.6154 | 0.3237 | 0.4780 | 0.070* | |
C8a | 0.38271 (16) | 0.29244 (13) | 0.42545 (15) | 0.0389 | |
C9 | 0.38332 (16) | 0.32361 (13) | 0.59363 (14) | 0.0397 | |
H91 | 0.4392 | 0.4273 | 0.6457 | 0.060* | |
C9a | 0.20861 (17) | 0.26797 (15) | 0.59627 (16) | 0.0453 | |
H9a1 | 0.1548 | 0.1638 | 0.5578 | 0.068* | |
C10 | 0.47708 (16) | 0.26796 (14) | 0.68466 (15) | 0.0423 | |
C11 | 0.4323 (2) | 0.12430 (16) | 0.63416 (19) | 0.0581 | |
H111 | 0.3460 | 0.0619 | 0.5417 | 0.087* | |
C12 | 0.5145 (2) | 0.0727 (2) | 0.7199 (2) | 0.0704 | |
H121 | 0.4820 | −0.0240 | 0.6852 | 0.106* | |
C13 | 0.6437 (2) | 0.1636 (2) | 0.8558 (2) | 0.0705 | |
H131 | 0.6990 | 0.1286 | 0.9129 | 0.106* | |
C14 | 0.6903 (2) | 0.3056 (2) | 0.90650 (19) | 0.0664 | |
H141 | 0.7781 | 0.3676 | 0.9980 | 0.100* | |
C15 | 0.60727 (18) | 0.35786 (17) | 0.82202 (16) | 0.0532 | |
H151 | 0.6395 | 0.4546 | 0.8582 | 0.080* | |
C16 | 0.0280 (2) | 0.3308 (3) | 0.2322 (2) | 0.0797 | |
H161 | −0.0712 | 0.3253 | 0.2477 | 0.120* | |
H162 | 0.0081 | 0.2902 | 0.1229 | 0.120* | |
H163 | 0.1115 | 0.4286 | 0.2726 | 0.120* | |
C17 | −0.0438 (2) | 0.0890 (2) | 0.2465 (2) | 0.0845 | |
H171 | −0.1486 | 0.0793 | 0.2488 | 0.127* | |
H172 | −0.0129 | 0.0385 | 0.3053 | 0.127* | |
H173 | −0.0505 | 0.0505 | 0.1406 | 0.127* | |
CgA | 0.3916 | 0.2671 | 0.2740 | 0* | |
CgD | 0.5609 | 0.2153 | 0.7705 | 0* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0785 (12) | 0.0933 (13) | 0.0546 (9) | 0.0508 (10) | 0.0387 (9) | 0.0325 (9) |
C2 | 0.0893 (15) | 0.145 (2) | 0.0900 (15) | 0.0742 (15) | 0.0592 (12) | 0.0518 (14) |
C3 | 0.0558 (10) | 0.0928 (14) | 0.0799 (12) | 0.0422 (10) | 0.0337 (9) | 0.0295 (10) |
C3a | 0.0421 (7) | 0.0508 (8) | 0.0534 (8) | 0.0246 (6) | 0.0172 (6) | 0.0185 (6) |
C4 | 0.0390 (7) | 0.0601 (9) | 0.0469 (8) | 0.0212 (6) | 0.0098 (6) | 0.0179 (7) |
C4a | 0.0449 (7) | 0.0452 (7) | 0.0415 (7) | 0.0217 (6) | 0.0147 (6) | 0.0165 (6) |
C5 | 0.0628 (9) | 0.0685 (10) | 0.0408 (7) | 0.0313 (8) | 0.0153 (7) | 0.0197 (7) |
C6 | 0.0778 (11) | 0.0756 (11) | 0.0495 (8) | 0.0426 (9) | 0.0338 (8) | 0.0272 (8) |
C7 | 0.0635 (9) | 0.0656 (9) | 0.0664 (10) | 0.0393 (8) | 0.0393 (8) | 0.0339 (8) |
C8 | 0.0455 (7) | 0.0522 (8) | 0.0535 (8) | 0.0267 (6) | 0.0217 (6) | 0.0263 (6) |
C8a | 0.0421 (7) | 0.0361 (6) | 0.0413 (7) | 0.0189 (5) | 0.0154 (5) | 0.0172 (5) |
C9 | 0.0428 (7) | 0.0390 (6) | 0.0393 (6) | 0.0209 (5) | 0.0136 (5) | 0.0152 (5) |
C9a | 0.0480 (7) | 0.0495 (7) | 0.0456 (7) | 0.0255 (6) | 0.0215 (6) | 0.0203 (6) |
C10 | 0.0449 (7) | 0.0485 (7) | 0.0410 (7) | 0.0249 (6) | 0.0180 (6) | 0.0207 (6) |
C11 | 0.0643 (9) | 0.0511 (8) | 0.0608 (9) | 0.0304 (7) | 0.0144 (7) | 0.0240 (7) |
C12 | 0.0854 (12) | 0.0691 (11) | 0.0849 (13) | 0.0507 (10) | 0.0347 (10) | 0.0437 (10) |
C13 | 0.0754 (11) | 0.1065 (15) | 0.0707 (11) | 0.0641 (11) | 0.0327 (9) | 0.0551 (11) |
C14 | 0.0609 (10) | 0.0938 (13) | 0.0505 (9) | 0.0428 (10) | 0.0131 (8) | 0.0301 (9) |
C15 | 0.0525 (8) | 0.0628 (9) | 0.0444 (8) | 0.0289 (7) | 0.0148 (6) | 0.0187 (7) |
C16 | 0.0668 (11) | 0.1282 (18) | 0.0726 (12) | 0.0643 (12) | 0.0233 (9) | 0.0511 (12) |
C17 | 0.0547 (10) | 0.0749 (12) | 0.0732 (12) | 0.0029 (9) | 0.0169 (9) | −0.0003 (9) |
Geometric parameters (Å, º) top
C1—C9a | 1.527 (2) | C8—C8a | 1.4005 (19) |
C1—C2 | 1.528 (3) | C8—H81 | 0.9300 |
C1—H11 | 0.9700 | C8a—C9 | 1.5308 (18) |
C1—H12 | 0.9700 | C9—C10 | 1.5163 (17) |
C2—C3 | 1.528 (3) | C9—C9a | 1.5224 (18) |
C2—H21 | 0.9700 | C9—H91 | 0.9800 |
C2—H22 | 0.9700 | C9a—H9a1 | 0.9800 |
C3—C3a | 1.540 (2) | C10—C15 | 1.385 (2) |
C3—H31 | 0.9700 | C10—C11 | 1.388 (2) |
C3—H32 | 0.9700 | C11—C12 | 1.384 (2) |
C3a—C4 | 1.533 (2) | C11—H111 | 0.9300 |
C3a—C9a | 1.5209 (19) | C12—C13 | 1.375 (3) |
C3a—H3a1 | 0.9800 | C12—H121 | 0.9300 |
C4—C4a | 1.5355 (19) | C13—C14 | 1.367 (3) |
C4—C17 | 1.539 (2) | C13—H131 | 0.9300 |
C4—C16 | 1.547 (2) | C14—C15 | 1.389 (2) |
C4a—C5 | 1.4027 (19) | C14—H141 | 0.9300 |
C4a—C8a | 1.4038 (19) | C15—H151 | 0.9300 |
C5—C6 | 1.373 (2) | C16—H161 | 0.9600 |
C5—H51 | 0.9300 | C16—H162 | 0.9600 |
C6—C7 | 1.372 (2) | C16—H163 | 0.9600 |
C6—H61 | 0.9300 | C17—H171 | 0.9600 |
C7—C8 | 1.380 (2) | C17—H172 | 0.9600 |
C7—H71 | 0.9300 | C17—H173 | 0.9600 |
| | | |
C9a—C1—C2 | 104.58 (14) | C8—C8a—C4a | 118.61 (12) |
C9a—C1—H11 | 110.8 | C8—C8a—C9 | 118.58 (11) |
C2—C1—H11 | 110.8 | C4a—C8a—C9 | 122.78 (12) |
C9a—C1—H12 | 110.8 | C10—C9—C9a | 111.80 (11) |
C2—C1—H12 | 110.8 | C10—C9—C8a | 113.00 (10) |
H11—C1—H12 | 108.9 | C9a—C9—C8a | 110.24 (11) |
C1—C2—C3 | 107.15 (15) | C10—C9—H91 | 107.2 |
C1—C2—H21 | 110.3 | C9a—C9—H91 | 107.2 |
C3—C2—H21 | 110.3 | C8a—C9—H91 | 107.2 |
C1—C2—H22 | 110.3 | C3a—C9a—C9 | 110.95 (11) |
C3—C2—H22 | 110.3 | C3a—C9a—C1 | 103.48 (12) |
H21—C2—H22 | 108.5 | C9—C9a—C1 | 116.29 (13) |
C2—C3—C3a | 105.52 (14) | C3a—C9a—H9a1 | 108.6 |
C2—C3—H31 | 110.6 | C9—C9a—H9a1 | 108.6 |
C3a—C3—H31 | 110.6 | C1—C9a—H9a1 | 108.6 |
C2—C3—H32 | 110.6 | C15—C10—C11 | 118.00 (13) |
C3a—C3—H32 | 110.6 | C15—C10—C9 | 121.25 (13) |
H31—C3—H32 | 108.8 | C11—C10—C9 | 120.74 (13) |
C9a—C3a—C4 | 113.35 (11) | C12—C11—C10 | 120.76 (16) |
C9a—C3a—C3 | 104.16 (13) | C12—C11—H111 | 119.6 |
C4—C3a—C3 | 118.91 (13) | C10—C11—H111 | 119.6 |
C9a—C3a—H3a1 | 106.6 | C13—C12—C11 | 120.48 (17) |
C4—C3a—H3a1 | 106.6 | C13—C12—H121 | 119.8 |
C3—C3a—H3a1 | 106.6 | C11—C12—H121 | 119.8 |
C3a—C4—C4a | 109.07 (11) | C14—C13—C12 | 119.48 (15) |
C3a—C4—C17 | 112.22 (13) | C14—C13—H131 | 120.3 |
C4a—C4—C17 | 108.11 (14) | C12—C13—H131 | 120.3 |
C3a—C4—C16 | 107.89 (13) | C13—C14—C15 | 120.35 (16) |
C4a—C4—C16 | 110.20 (13) | C13—C14—H141 | 119.8 |
C17—C4—C16 | 109.36 (15) | C15—C14—H141 | 119.8 |
C5—C4a—C8a | 117.87 (13) | C10—C15—C14 | 120.93 (16) |
C5—C4a—C4 | 118.68 (13) | C10—C15—H151 | 119.5 |
C8a—C4a—C4 | 123.40 (12) | C14—C15—H151 | 119.5 |
C6—C5—C4a | 122.64 (15) | C4—C16—H161 | 109.5 |
C6—C5—H51 | 118.7 | C4—C16—H162 | 109.5 |
C4a—C5—H51 | 118.7 | H161—C16—H162 | 109.5 |
C7—C6—C5 | 119.20 (14) | C4—C16—H163 | 109.5 |
C7—C6—H61 | 120.4 | H161—C16—H163 | 109.5 |
C5—C6—H61 | 120.4 | H162—C16—H163 | 109.5 |
C6—C7—C8 | 119.97 (14) | C4—C17—H171 | 109.5 |
C6—C7—H71 | 120.0 | C4—C17—H172 | 109.5 |
C8—C7—H71 | 120.0 | H171—C17—H172 | 109.5 |
C7—C8—C8a | 121.69 (14) | C4—C17—H173 | 109.5 |
C7—C8—H81 | 119.2 | H171—C17—H173 | 109.5 |
C8a—C8—H81 | 119.2 | H172—C17—H173 | 109.5 |
| | | |
C9a—C1—C2—C3 | −19.5 (2) | C8—C8a—C9—C10 | −37.39 (16) |
C1—C2—C3—C3a | −4.2 (2) | C4a—C8a—C9—C10 | 144.64 (12) |
C2—C3—C3a—C9a | 26.40 (19) | C8—C8a—C9—C9a | −163.31 (11) |
C2—C3—C3a—C4 | 153.73 (16) | C4a—C8a—C9—C9a | 18.72 (16) |
C9a—C3a—C4—C4a | −45.62 (16) | C4—C3a—C9a—C9 | 65.33 (15) |
C3—C3a—C4—C4a | −168.49 (14) | C3—C3a—C9a—C9 | −163.98 (12) |
C9a—C3a—C4—C17 | 74.14 (17) | C4—C3a—C9a—C1 | −169.25 (13) |
C3—C3a—C4—C17 | −48.7 (2) | C3—C3a—C9a—C1 | −38.57 (16) |
C9a—C3a—C4—C16 | −165.32 (13) | C10—C9—C9a—C3a | −174.55 (11) |
C3—C3a—C4—C16 | 71.81 (18) | C8a—C9—C9a—C3a | −47.97 (14) |
C3a—C4—C4a—C5 | −167.22 (13) | C10—C9—C9a—C1 | 67.56 (16) |
C17—C4—C4a—C5 | 70.50 (18) | C8a—C9—C9a—C1 | −165.85 (12) |
C16—C4—C4a—C5 | −48.96 (19) | C2—C1—C9a—C3a | 35.91 (18) |
C3a—C4—C4a—C8a | 15.20 (18) | C2—C1—C9a—C9 | 157.82 (15) |
C17—C4—C4a—C8a | −107.08 (17) | C9a—C9—C10—C15 | −112.21 (14) |
C16—C4—C4a—C8a | 133.46 (15) | C8a—C9—C10—C15 | 122.72 (14) |
C8a—C4a—C5—C6 | −1.1 (2) | C9a—C9—C10—C11 | 66.37 (17) |
C4—C4a—C5—C6 | −178.82 (15) | C8a—C9—C10—C11 | −58.71 (17) |
C4a—C5—C6—C7 | −0.3 (3) | C15—C10—C11—C12 | 0.7 (2) |
C5—C6—C7—C8 | 0.8 (2) | C9—C10—C11—C12 | −177.90 (14) |
C6—C7—C8—C8a | 0.1 (2) | C10—C11—C12—C13 | −0.9 (3) |
C7—C8—C8a—C4a | −1.5 (2) | C11—C12—C13—C14 | 0.3 (3) |
C7—C8—C8a—C9 | −179.52 (12) | C12—C13—C14—C15 | 0.4 (3) |
C5—C4a—C8a—C8 | 1.92 (19) | C11—C10—C15—C14 | 0.0 (2) |
C4—C4a—C8a—C8 | 179.52 (12) | C9—C10—C15—C14 | 178.61 (13) |
C5—C4a—C8a—C9 | 179.89 (12) | C13—C14—C15—C10 | −0.6 (3) |
C4—C4a—C8a—C9 | −2.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H91···C4ai | 0.98 | 3.34 | 4.198 (2) | 147 |
C9—H91···C5i | 0.98 | 3.38 | 4.317 (3) | 161 |
C9—H91···C6i | 0.98 | 3.27 | 4.240 (3) | 169 |
C9—H91···C7i | 0.98 | 3.08 | 3.995 (2) | 156 |
C9—H91···C8i | 0.98 | 3.01 | 3.848 (2) | 144 |
C9—H91···C8ai | 0.98 | 3.17 | 3.975 (2) | 140 |
C9—H91···CgAi | 0.98 | 2.90 | 3.86 | 166 |
C6—H61···C10ii | 0.93 | 3.50 | 4.392 (2) | 162 |
C6—H61···C11ii | 0.93 | 3.64 | 4.572 (3) | 175 |
C6—H61···C12ii | 0.93 | 3.49 | 4.341 (3) | 153 |
C6—H61···C13ii | 0.93 | 3.18 | 3.905 (3) | 136 |
C6—H61···C14ii | 0.93 | 3.00 | 3.687 (3) | 131 |
C6—H61···C15ii | 0.93 | 3.16 | 3.939 (2) | 142 |
C6—H61···CgDii | 0.93 | 3.04 | 3.91 | 157 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1. |
(II) 3a,4-
trans-3a,9a-
cis-9,9a-
trans-4-methoxy-9- phenyl-2,3,3a,4,9,9a-hexahydrobenzo[
f]indene
top
Crystal data top
C20H22O | Z = 4 |
Mr = 278.38 | F(000) = 600 |
Triclinic, P1 | Dx = 1.234 Mg m−3 |
a = 9.0001 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 19.287 (2) Å | Cell parameters from 25 reflections |
c = 8.9918 (8) Å | θ = 14–15° |
α = 96.654 (8)° | µ = 0.07 mm−1 |
β = 101.494 (7)° | T = 100 K |
γ = 97.908 (8)° | Block, colourless |
V = 1498.4 (2) Å3 | 0.30 × 0.19 × 0.12 mm |
Data collection top
Rigaku AFC-7R diffractometer | 6799 reflections with I > 2σ(I) |
Radiation source: normal-focus rotating anode | Rint = 0.016 |
Graphite monochromator | θmax = 30.0°, θmin = 2.4° |
ω/2θ scan | h = −8→12 |
Absorption correction: ψ-scan North et al., 1968 | k = −27→26 |
Tmin = 0.965, Tmax = 0.991 | l = −12→12 |
12299 measured reflections | 3 standard reflections every 100 reflections |
8747 independent reflections | intensity decay: 0.7% |
Refinement top
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)] = 0.042 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.121 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0585P)2 + 0.3481P] where P = (Fo2 + 2Fc2)/3 |
8747 reflections | (Δ/σ)max < 0.001 |
555 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Crystal data top
C20H22O | γ = 97.908 (8)° |
Mr = 278.38 | V = 1498.4 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.0001 (8) Å | Mo Kα radiation |
b = 19.287 (2) Å | µ = 0.07 mm−1 |
c = 8.9918 (8) Å | T = 100 K |
α = 96.654 (8)° | 0.30 × 0.19 × 0.12 mm |
β = 101.494 (7)° | |
Data collection top
Rigaku AFC-7R diffractometer | 6799 reflections with I > 2σ(I) |
Absorption correction: ψ-scan North et al., 1968 | Rint = 0.016 |
Tmin = 0.965, Tmax = 0.991 | 3 standard reflections every 100 reflections |
12299 measured reflections | intensity decay: 0.7% |
8747 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.121 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.43 e Å−3 |
8747 reflections | Δρmin = −0.26 e Å−3 |
555 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1X | 0.17475 (13) | 0.07985 (6) | 0.89731 (12) | 0.0177 | |
H11X | 0.2807 (16) | 0.0761 (7) | 0.9538 (16) | 0.015 (3)* | |
H12X | 0.0987 (17) | 0.0504 (8) | 0.9395 (17) | 0.024 (4)* | |
C2X | 0.15187 (14) | 0.15727 (6) | 0.90588 (13) | 0.0196 | |
H21X | 0.1950 (18) | 0.1850 (8) | 1.0097 (18) | 0.028 (4)* | |
H22X | 0.0413 (17) | 0.1608 (7) | 0.8808 (16) | 0.020 (3)* | |
C3X | 0.22946 (14) | 0.18390 (6) | 0.78181 (13) | 0.0193 | |
H31X | 0.1994 (17) | 0.2301 (8) | 0.7501 (17) | 0.024 (4)* | |
H32X | 0.3442 (17) | 0.1909 (7) | 0.8174 (16) | 0.020 (3)* | |
C3aX | 0.18343 (12) | 0.12211 (5) | 0.64901 (11) | 0.01424 | |
H3a1X | 0.0816 (16) | 0.1261 (7) | 0.5830 (15) | 0.015 (3)* | |
C4X | 0.29768 (12) | 0.12076 (5) | 0.54401 (12) | 0.01476 | |
H41X | 0.4020 (16) | 0.1307 (7) | 0.6086 (15) | 0.014 (3)* | |
C4aX | 0.27782 (12) | 0.04863 (5) | 0.44914 (12) | 0.01446 | |
C5X | 0.26173 (12) | 0.03805 (6) | 0.29039 (12) | 0.0170 | |
H51X | 0.2577 (17) | 0.0791 (8) | 0.2372 (17) | 0.021 (3)* | |
C6X | 0.25213 (13) | −0.02969 (6) | 0.21175 (12) | 0.0188 | |
H61X | 0.2380 (16) | −0.0368 (8) | 0.0998 (17) | 0.020 (3)* | |
C7X | 0.26092 (13) | −0.08684 (6) | 0.29251 (12) | 0.0188 | |
H71X | 0.2566 (18) | −0.1342 (8) | 0.2366 (17) | 0.025 (4)* | |
C8X | 0.27185 (12) | −0.07690 (6) | 0.45070 (12) | 0.01623 | |
H81X | 0.2769 (17) | −0.1180 (8) | 0.5054 (17) | 0.024 (4)* | |
C8aX | 0.27786 (11) | −0.00968 (5) | 0.52969 (11) | 0.01377 | |
C9X | 0.28187 (12) | 0.00529 (5) | 0.70043 (11) | 0.01334 | |
H91X | 0.3874 (17) | 0.0333 (7) | 0.7522 (16) | 0.019 (3)* | |
C9aX | 0.16330 (12) | 0.05382 (5) | 0.72561 (11) | 0.01406 | |
H9a1X | 0.0599 (17) | 0.0264 (7) | 0.6788 (17) | 0.020 (3)* | |
C10X | 0.25862 (12) | −0.06166 (5) | 0.77241 (11) | 0.01416 | |
C11X | 0.38367 (12) | −0.08411 (6) | 0.86041 (12) | 0.01648 | |
H111X | 0.4874 (18) | −0.0551 (8) | 0.8767 (17) | 0.025 (4)* | |
C12X | 0.36443 (14) | −0.14673 (6) | 0.92318 (13) | 0.0208 | |
H121X | 0.4562 (19) | −0.1619 (8) | 0.9858 (18) | 0.030 (4)* | |
C13X | 0.22016 (14) | −0.18770 (6) | 0.89813 (13) | 0.0215 | |
H131X | 0.2092 (18) | −0.2317 (8) | 0.9406 (18) | 0.027 (4)* | |
C14X | 0.09434 (13) | −0.16591 (6) | 0.81039 (13) | 0.0204 | |
H141X | −0.0069 (18) | −0.1935 (8) | 0.7924 (17) | 0.026 (4)* | |
C15X | 0.11375 (13) | −0.10325 (6) | 0.74822 (12) | 0.0177 | |
H151X | 0.0255 (17) | −0.0886 (8) | 0.6892 (17) | 0.022 (4)* | |
O1X | 0.28090 (10) | 0.17657 (4) | 0.45421 (9) | 0.01998 | |
C16X | 0.42121 (16) | 0.20589 (7) | 0.41787 (16) | 0.0275 | |
H161X | 0.5030 (19) | 0.2249 (8) | 0.5145 (19) | 0.031 (4)* | |
H162X | 0.3966 (19) | 0.2451 (9) | 0.3624 (19) | 0.033 (4)* | |
H163X | 0.460 (2) | 0.1708 (9) | 0.352 (2) | 0.038 (5)* | |
CgAX | 0.2671 | −0.0194 | 0.3707 | 0* | |
CgDX | 0.2392 | −0.1249 | 0.8355 | 0* | |
C1Y | 0.09569 (13) | 0.45094 (6) | 0.26877 (15) | 0.0223 | |
H11Y | 0.0479 (18) | 0.4724 (8) | 0.1756 (18) | 0.028 (4)* | |
H12Y | 0.0476 (19) | 0.4665 (9) | 0.3552 (19) | 0.033 (4)* | |
C2Y | 0.06822 (13) | 0.37070 (6) | 0.22366 (15) | 0.0230 | |
H21Y | −0.0401 (19) | 0.3507 (8) | 0.1614 (18) | 0.030 (4)* | |
H22Y | 0.0823 (18) | 0.3470 (8) | 0.3193 (18) | 0.027 (4)* | |
C3Y | 0.19496 (14) | 0.35885 (7) | 0.13737 (15) | 0.0259 | |
H31Y | 0.210 (2) | 0.3089 (9) | 0.1257 (19) | 0.036 (4)* | |
H32Y | 0.170 (2) | 0.3739 (9) | 0.032 (2) | 0.037 (4)* | |
C3aY | 0.33807 (12) | 0.40931 (6) | 0.23547 (12) | 0.0172 | |
H3a1Y | 0.3876 (18) | 0.3864 (8) | 0.3233 (17) | 0.026 (4)* | |
C4Y | 0.46475 (12) | 0.43085 (6) | 0.14870 (12) | 0.01668 | |
H41Y | 0.4119 (16) | 0.4373 (7) | 0.0397 (16) | 0.018 (3)* | |
C4aY | 0.56725 (12) | 0.49936 (5) | 0.22675 (12) | 0.01587 | |
C5Y | 0.72681 (12) | 0.50830 (6) | 0.24910 (13) | 0.0185 | |
H51Y | 0.7749 (19) | 0.4678 (9) | 0.2162 (18) | 0.030 (4)* | |
C6Y | 0.81655 (13) | 0.57324 (6) | 0.31727 (13) | 0.0202 | |
H61Y | 0.9270 (19) | 0.5792 (8) | 0.3311 (18) | 0.030 (4)* | |
C7Y | 0.74637 (13) | 0.62956 (6) | 0.36203 (13) | 0.0198 | |
H71Y | 0.8084 (18) | 0.6766 (8) | 0.4092 (18) | 0.026 (4)* | |
C8Y | 0.58678 (12) | 0.62097 (6) | 0.33945 (12) | 0.0171 | |
H81Y | 0.5373 (16) | 0.6608 (7) | 0.3674 (16) | 0.017 (3)* | |
C8aY | 0.49613 (12) | 0.55611 (5) | 0.27217 (12) | 0.01517 | |
C9Y | 0.32202 (12) | 0.54230 (5) | 0.24341 (12) | 0.01526 | |
H91Y | 0.2791 (17) | 0.5327 (8) | 0.1258 (17) | 0.022 (3)* | |
C9aY | 0.27206 (12) | 0.47359 (5) | 0.30533 (12) | 0.01601 | |
H9a1Y | 0.3120 (16) | 0.4811 (7) | 0.4184 (16) | 0.016 (3)* | |
C10Y | 0.25510 (12) | 0.60448 (5) | 0.30606 (13) | 0.0169 | |
C11Y | 0.18400 (13) | 0.64635 (6) | 0.20634 (15) | 0.0225 | |
H111Y | 0.1765 (18) | 0.6335 (8) | 0.0975 (18) | 0.027 (4)* | |
C12Y | 0.12451 (15) | 0.70474 (7) | 0.26193 (18) | 0.0291 | |
H121Y | 0.074 (2) | 0.7316 (9) | 0.191 (2) | 0.038 (5)* | |
C13Y | 0.13645 (15) | 0.72235 (6) | 0.41807 (18) | 0.0306 | |
H131Y | 0.094 (2) | 0.7634 (9) | 0.460 (2) | 0.038 (5)* | |
C14Y | 0.20719 (14) | 0.68123 (7) | 0.51869 (16) | 0.0265 | |
H141Y | 0.2187 (19) | 0.6938 (9) | 0.628 (2) | 0.034 (4)* | |
C15Y | 0.26564 (13) | 0.62262 (6) | 0.46337 (14) | 0.0209 | |
H151Y | 0.3185 (17) | 0.5949 (8) | 0.5361 (17) | 0.022 (4)* | |
O1Y | 0.56203 (10) | 0.37890 (4) | 0.13506 (10) | 0.02288 | |
C16Y | 0.49376 (15) | 0.31733 (6) | 0.02903 (15) | 0.0246 | |
H161Y | 0.4362 (19) | 0.2808 (8) | 0.0787 (18) | 0.030 (4)* | |
H162Y | 0.4204 (18) | 0.3285 (8) | −0.0609 (18) | 0.027 (4)* | |
H163Y | 0.580 (2) | 0.2982 (9) | −0.003 (2) | 0.042 (5)* | |
CgAY | 0.6566 | 0.5646 | 0.2945 | 0* | |
CgDY | 0.1955 | 0.6636 | 0.3618 | 0* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1X | 0.0227 (5) | 0.0176 (5) | 0.0138 (4) | 0.0042 (4) | 0.0056 (4) | 0.0024 (4) |
C2X | 0.0252 (6) | 0.0177 (5) | 0.0169 (5) | 0.0049 (4) | 0.0072 (4) | 0.0004 (4) |
C3X | 0.0257 (6) | 0.0148 (5) | 0.0172 (5) | 0.0029 (4) | 0.0057 (4) | 0.0005 (4) |
C3aX | 0.0160 (5) | 0.0141 (4) | 0.0131 (4) | 0.0034 (3) | 0.0034 (4) | 0.0025 (3) |
C4X | 0.0159 (5) | 0.0140 (4) | 0.0151 (4) | 0.0027 (4) | 0.0038 (4) | 0.0040 (3) |
C4aX | 0.0133 (4) | 0.0155 (4) | 0.0149 (4) | 0.0023 (3) | 0.0038 (3) | 0.0026 (3) |
C5X | 0.0179 (5) | 0.0190 (5) | 0.0152 (5) | 0.0026 (4) | 0.0054 (4) | 0.0046 (4) |
C6X | 0.0210 (5) | 0.0220 (5) | 0.0137 (4) | 0.0027 (4) | 0.0060 (4) | 0.0012 (4) |
C7X | 0.0208 (5) | 0.0179 (5) | 0.0175 (5) | 0.0027 (4) | 0.0058 (4) | −0.0004 (4) |
C8X | 0.0178 (5) | 0.0156 (5) | 0.0161 (5) | 0.0034 (4) | 0.0049 (4) | 0.0026 (4) |
C8aX | 0.0126 (4) | 0.0160 (4) | 0.0131 (4) | 0.0027 (3) | 0.0034 (3) | 0.0020 (3) |
C9X | 0.0138 (4) | 0.0135 (4) | 0.0126 (4) | 0.0020 (3) | 0.0025 (3) | 0.0024 (3) |
C9aX | 0.0146 (4) | 0.0145 (4) | 0.0131 (4) | 0.0026 (3) | 0.0029 (3) | 0.0020 (3) |
C10X | 0.0168 (5) | 0.0142 (4) | 0.0121 (4) | 0.0035 (4) | 0.0040 (3) | 0.0019 (3) |
C11X | 0.0163 (5) | 0.0168 (5) | 0.0166 (5) | 0.0039 (4) | 0.0035 (4) | 0.0024 (4) |
C12X | 0.0243 (5) | 0.0189 (5) | 0.0205 (5) | 0.0078 (4) | 0.0034 (4) | 0.0056 (4) |
C13X | 0.0292 (6) | 0.0161 (5) | 0.0211 (5) | 0.0041 (4) | 0.0080 (4) | 0.0059 (4) |
C14X | 0.0210 (5) | 0.0181 (5) | 0.0221 (5) | −0.0001 (4) | 0.0070 (4) | 0.0029 (4) |
C15X | 0.0170 (5) | 0.0182 (5) | 0.0178 (5) | 0.0023 (4) | 0.0030 (4) | 0.0036 (4) |
O1X | 0.0253 (4) | 0.0167 (4) | 0.0218 (4) | 0.0053 (3) | 0.0097 (3) | 0.0089 (3) |
C16X | 0.0349 (7) | 0.0193 (5) | 0.0323 (6) | 0.0001 (5) | 0.0189 (5) | 0.0056 (5) |
C1Y | 0.0150 (5) | 0.0207 (5) | 0.0312 (6) | 0.0017 (4) | 0.0056 (4) | 0.0047 (4) |
C2Y | 0.0166 (5) | 0.0216 (5) | 0.0280 (6) | −0.0030 (4) | 0.0037 (4) | 0.0018 (4) |
C3Y | 0.0212 (5) | 0.0216 (6) | 0.0311 (6) | −0.0038 (4) | 0.0067 (5) | −0.0050 (5) |
C3aY | 0.0159 (5) | 0.0152 (4) | 0.0197 (5) | 0.0017 (4) | 0.0028 (4) | 0.0026 (4) |
C4Y | 0.0163 (5) | 0.0155 (5) | 0.0182 (5) | 0.0045 (4) | 0.0029 (4) | 0.0018 (4) |
C4aY | 0.0148 (5) | 0.0165 (5) | 0.0164 (4) | 0.0024 (4) | 0.0027 (4) | 0.0040 (4) |
C5Y | 0.0152 (5) | 0.0200 (5) | 0.0216 (5) | 0.0043 (4) | 0.0052 (4) | 0.0044 (4) |
C6Y | 0.0140 (5) | 0.0219 (5) | 0.0252 (5) | 0.0015 (4) | 0.0046 (4) | 0.0067 (4) |
C7Y | 0.0171 (5) | 0.0184 (5) | 0.0229 (5) | −0.0005 (4) | 0.0031 (4) | 0.0053 (4) |
C8Y | 0.0174 (5) | 0.0157 (5) | 0.0187 (5) | 0.0020 (4) | 0.0045 (4) | 0.0040 (4) |
C8aY | 0.0131 (4) | 0.0174 (5) | 0.0154 (4) | 0.0026 (4) | 0.0028 (4) | 0.0047 (4) |
C9Y | 0.0134 (4) | 0.0149 (4) | 0.0176 (5) | 0.0035 (3) | 0.0024 (4) | 0.0033 (4) |
C9aY | 0.0146 (5) | 0.0152 (4) | 0.0183 (5) | 0.0020 (4) | 0.0039 (4) | 0.0029 (4) |
C10Y | 0.0122 (4) | 0.0149 (4) | 0.0240 (5) | 0.0018 (3) | 0.0048 (4) | 0.0030 (4) |
C11Y | 0.0198 (5) | 0.0201 (5) | 0.0300 (6) | 0.0054 (4) | 0.0070 (4) | 0.0083 (4) |
C12Y | 0.0219 (6) | 0.0188 (5) | 0.0503 (8) | 0.0074 (4) | 0.0100 (5) | 0.0122 (5) |
C13Y | 0.0206 (6) | 0.0157 (5) | 0.0569 (9) | 0.0025 (4) | 0.0155 (6) | −0.0009 (5) |
C14Y | 0.0217 (6) | 0.0223 (5) | 0.0342 (7) | −0.0011 (4) | 0.0119 (5) | −0.0058 (5) |
C15Y | 0.0173 (5) | 0.0202 (5) | 0.0248 (5) | 0.0024 (4) | 0.0059 (4) | 0.0008 (4) |
O1Y | 0.0196 (4) | 0.0183 (4) | 0.0294 (4) | 0.0067 (3) | 0.0029 (3) | −0.0024 (3) |
C16Y | 0.0294 (6) | 0.0188 (5) | 0.0262 (6) | 0.0059 (5) | 0.0088 (5) | −0.0013 (4) |
Geometric parameters (Å, º) top
C1X—C2X | 1.5304 (15) | C1Y—C2Y | 1.5265 (17) |
C1X—C9aX | 1.5456 (14) | C1Y—C9aY | 1.5448 (15) |
C1X—H11X | 1.004 (14) | C1Y—H11Y | 1.022 (16) |
C1X—H12X | 0.990 (15) | C1Y—H12Y | 0.998 (17) |
C2X—C3X | 1.5299 (16) | C2Y—C3Y | 1.5293 (17) |
C2X—H21X | 0.996 (16) | C2Y—H21Y | 1.021 (16) |
C2X—H22X | 0.989 (15) | C2Y—H22Y | 1.014 (16) |
C3X—C3aX | 1.5346 (14) | C3Y—C3aY | 1.5451 (16) |
C3X—H31X | 1.022 (15) | C3Y—H31Y | 0.987 (17) |
C3X—H32X | 1.003 (15) | C3Y—H32Y | 1.010 (17) |
C3aX—C4X | 1.5290 (14) | C3aY—C4Y | 1.5428 (15) |
C3aX—C9aX | 1.5609 (14) | C3aY—C9aY | 1.5670 (15) |
C3aX—H3a1X | 1.006 (14) | C3aY—H3a1Y | 1.007 (15) |
C4X—O1X | 1.4251 (12) | C4Y—O1Y | 1.4287 (13) |
C4X—C4aX | 1.5136 (14) | C4Y—C4aY | 1.5105 (15) |
C4X—H41X | 0.981 (14) | C4Y—H41Y | 1.029 (14) |
C4aX—C5X | 1.3936 (14) | C4aY—C5Y | 1.3932 (15) |
C4aX—C8aX | 1.4065 (14) | C4aY—C8aY | 1.4028 (14) |
C5X—C6X | 1.3945 (15) | C5Y—C6Y | 1.3942 (16) |
C5X—H51X | 0.972 (15) | C5Y—H51Y | 0.989 (16) |
C6X—C7X | 1.3910 (15) | C6Y—C7Y | 1.3891 (16) |
C6X—H61X | 0.980 (14) | C6Y—H61Y | 0.966 (16) |
C7X—C8X | 1.3949 (14) | C7Y—C8Y | 1.3936 (15) |
C7X—H71X | 0.982 (15) | C7Y—H71Y | 0.996 (16) |
C8X—C8aX | 1.3931 (14) | C8Y—C8aY | 1.3942 (15) |
C8X—H81X | 0.981 (15) | C8Y—H81Y | 0.972 (14) |
C8aX—C9X | 1.5211 (14) | C8aY—C9Y | 1.5169 (14) |
C9X—C10X | 1.5177 (14) | C9Y—C10Y | 1.5152 (14) |
C9X—C9aX | 1.5455 (14) | C9Y—C9aY | 1.5413 (15) |
C9X—H91X | 1.017 (15) | C9Y—H91Y | 1.036 (15) |
C9aX—H9a1X | 0.990 (15) | C9aY—H9a1Y | 0.995 (14) |
C10X—C11X | 1.3925 (14) | C10Y—C11Y | 1.3954 (16) |
C10X—C15X | 1.3963 (15) | C10Y—C15Y | 1.3982 (16) |
C11X—C12X | 1.3951 (15) | C11Y—C12Y | 1.3954 (17) |
C11X—H111X | 0.994 (16) | C11Y—H111Y | 0.968 (16) |
C12X—C13X | 1.3860 (17) | C12Y—C13Y | 1.385 (2) |
C12X—H121X | 1.003 (16) | C12Y—H121Y | 0.953 (18) |
C13X—C14X | 1.3904 (17) | C13Y—C14Y | 1.389 (2) |
C13X—H131X | 0.971 (16) | C13Y—H131Y | 0.992 (18) |
C14X—C15X | 1.3932 (15) | C14Y—C15Y | 1.3927 (16) |
C14X—H141X | 0.963 (16) | C14Y—H141Y | 0.966 (17) |
C15X—H151X | 0.960 (15) | C15Y—H151Y | 0.984 (15) |
O1X—C16X | 1.4254 (15) | O1Y—C16Y | 1.4142 (14) |
C16X—H161X | 1.014 (17) | C16Y—H161Y | 1.014 (16) |
C16X—H162X | 0.979 (17) | C16Y—H162Y | 1.002 (16) |
C16X—H163X | 0.992 (18) | C16Y—H163Y | 0.984 (18) |
| | | |
C2X—C1X—C9aX | 105.46 (8) | C2Y—C1Y—C9aY | 105.37 (9) |
C2X—C1X—H11X | 110.8 (8) | C2Y—C1Y—H11Y | 107.9 (9) |
C9aX—C1X—H11X | 107.3 (8) | C9aY—C1Y—H11Y | 109.3 (9) |
C2X—C1X—H12X | 112.8 (9) | C2Y—C1Y—H12Y | 113.1 (9) |
C9aX—C1X—H12X | 111.8 (9) | C9aY—C1Y—H12Y | 113.2 (10) |
H11X—C1X—H12X | 108.6 (11) | H11Y—C1Y—H12Y | 107.8 (13) |
C3X—C2X—C1X | 103.34 (9) | C1Y—C2Y—C3Y | 103.01 (9) |
C3X—C2X—H21X | 113.4 (9) | C1Y—C2Y—H21Y | 113.4 (9) |
C1X—C2X—H21X | 112.9 (9) | C3Y—C2Y—H21Y | 113.9 (9) |
C3X—C2X—H22X | 109.8 (8) | C1Y—C2Y—H22Y | 109.8 (9) |
C1X—C2X—H22X | 110.9 (8) | C3Y—C2Y—H22Y | 110.3 (9) |
H21X—C2X—H22X | 106.6 (12) | H21Y—C2Y—H22Y | 106.4 (13) |
C2X—C3X—C3aX | 103.94 (9) | C2Y—C3Y—C3aY | 103.70 (9) |
C2X—C3X—H31X | 113.8 (9) | C2Y—C3Y—H31Y | 112.0 (10) |
C3aX—C3X—H31X | 112.8 (8) | C3aY—C3Y—H31Y | 112.8 (10) |
C2X—C3X—H32X | 110.2 (8) | C2Y—C3Y—H32Y | 110.5 (10) |
C3aX—C3X—H32X | 107.4 (8) | C3aY—C3Y—H32Y | 108.7 (10) |
H31X—C3X—H32X | 108.4 (12) | H31Y—C3Y—H32Y | 109.1 (14) |
C4X—C3aX—C3X | 113.41 (9) | C4Y—C3aY—C3Y | 114.90 (9) |
C4X—C3aX—C9aX | 113.04 (8) | C4Y—C3aY—C9aY | 113.56 (8) |
C3X—C3aX—C9aX | 105.60 (8) | C3Y—C3aY—C9aY | 104.37 (9) |
C4X—C3aX—H3a1X | 106.7 (8) | C4Y—C3aY—H3a1Y | 106.3 (9) |
C3X—C3aX—H3a1X | 109.4 (8) | C3Y—C3aY—H3a1Y | 110.1 (9) |
C9aX—C3aX—H3a1X | 108.6 (8) | C9aY—C3aY—H3a1Y | 107.5 (9) |
O1X—C4X—C4aX | 113.56 (8) | O1Y—C4Y—C4aY | 107.09 (8) |
O1X—C4X—C3aX | 108.15 (8) | O1Y—C4Y—C3aY | 113.08 (9) |
C4aX—C4X—C3aX | 111.29 (8) | C4aY—C4Y—C3aY | 111.73 (9) |
O1X—C4X—H41X | 107.7 (8) | O1Y—C4Y—H41Y | 107.9 (8) |
C4aX—C4X—H41X | 107.8 (8) | C4aY—C4Y—H41Y | 109.0 (8) |
C3aX—C4X—H41X | 108.2 (8) | C3aY—C4Y—H41Y | 107.9 (8) |
C5X—C4aX—C8aX | 119.82 (9) | C5Y—C4aY—C8aY | 119.91 (10) |
C5X—C4aX—C4X | 123.66 (9) | C5Y—C4aY—C4Y | 122.41 (10) |
C8aX—C4aX—C4X | 116.52 (9) | C8aY—C4aY—C4Y | 117.63 (9) |
C4aX—C5X—C6X | 120.36 (10) | C4aY—C5Y—C6Y | 120.41 (10) |
C4aX—C5X—H51X | 118.0 (9) | C4aY—C5Y—H51Y | 118.8 (10) |
C6X—C5X—H51X | 121.6 (9) | C6Y—C5Y—H51Y | 120.8 (10) |
C7X—C6X—C5X | 119.80 (10) | C7Y—C6Y—C5Y | 119.79 (10) |
C7X—C6X—H61X | 120.4 (8) | C7Y—C6Y—H61Y | 120.3 (10) |
C5X—C6X—H61X | 119.8 (8) | C5Y—C6Y—H61Y | 119.9 (9) |
C6X—C7X—C8X | 120.04 (10) | C6Y—C7Y—C8Y | 120.03 (10) |
C6X—C7X—H71X | 119.3 (9) | C6Y—C7Y—H71Y | 120.9 (9) |
C8X—C7X—H71X | 120.6 (9) | C8Y—C7Y—H71Y | 119.0 (9) |
C8aX—C8X—C7X | 120.51 (10) | C7Y—C8Y—C8aY | 120.60 (10) |
C8aX—C8X—H81X | 120.7 (9) | C7Y—C8Y—H81Y | 120.1 (8) |
C7X—C8X—H81X | 118.8 (9) | C8aY—C8Y—H81Y | 119.3 (8) |
C8X—C8aX—C4aX | 119.32 (9) | C8Y—C8aY—C4aY | 119.27 (9) |
C8X—C8aX—C9X | 123.90 (9) | C8Y—C8aY—C9Y | 123.96 (9) |
C4aX—C8aX—C9X | 116.77 (9) | C4aY—C8aY—C9Y | 116.77 (9) |
C10X—C9X—C8aX | 112.83 (8) | C10Y—C9Y—C8aY | 113.42 (9) |
C10X—C9X—C9aX | 112.31 (8) | C10Y—C9Y—C9aY | 113.05 (9) |
C8aX—C9X—C9aX | 109.06 (8) | C8aY—C9Y—C9aY | 108.44 (8) |
C10X—C9X—H91X | 108.3 (8) | C10Y—C9Y—H91Y | 107.1 (8) |
C8aX—C9X—H91X | 107.3 (8) | C8aY—C9Y—H91Y | 108.0 (8) |
C9aX—C9X—H91X | 106.8 (8) | C9aY—C9Y—H91Y | 106.5 (8) |
C9X—C9aX—C1X | 112.47 (8) | C9Y—C9aY—C1Y | 112.67 (9) |
C9X—C9aX—C3aX | 112.91 (8) | C9Y—C9aY—C3aY | 112.37 (8) |
C1X—C9aX—C3aX | 105.67 (8) | C1Y—C9aY—C3aY | 106.04 (9) |
C9X—C9aX—H9a1X | 107.4 (8) | C9Y—C9aY—H9a1Y | 108.5 (8) |
C1X—C9aX—H9a1X | 110.1 (8) | C1Y—C9aY—H9a1Y | 109.5 (8) |
C3aX—C9aX—H9a1X | 108.3 (8) | C3aY—C9aY—H9a1Y | 107.7 (8) |
C11X—C10X—C15X | 118.53 (9) | C11Y—C10Y—C15Y | 118.30 (10) |
C11X—C10X—C9X | 120.17 (9) | C11Y—C10Y—C9Y | 120.01 (10) |
C15X—C10X—C9X | 121.27 (9) | C15Y—C10Y—C9Y | 121.67 (10) |
C10X—C11X—C12X | 120.68 (10) | C12Y—C11Y—C10Y | 120.93 (12) |
C10X—C11X—H111X | 118.9 (9) | C12Y—C11Y—H111Y | 121.0 (9) |
C12X—C11X—H111X | 120.5 (9) | C10Y—C11Y—H111Y | 118.1 (9) |
C13X—C12X—C11X | 120.31 (10) | C13Y—C12Y—C11Y | 120.18 (12) |
C13X—C12X—H121X | 120.4 (9) | C13Y—C12Y—H121Y | 120.6 (10) |
C11X—C12X—H121X | 119.3 (9) | C11Y—C12Y—H121Y | 119.2 (10) |
C12X—C13X—C14X | 119.59 (10) | C12Y—C13Y—C14Y | 119.51 (11) |
C12X—C13X—H131X | 119.2 (9) | C12Y—C13Y—H131Y | 121.3 (10) |
C14X—C13X—H131X | 121.2 (9) | C14Y—C13Y—H131Y | 119.2 (10) |
C13X—C14X—C15X | 119.99 (10) | C13Y—C14Y—C15Y | 120.41 (12) |
C13X—C14X—H141X | 120.7 (9) | C13Y—C14Y—H141Y | 120.1 (10) |
C15X—C14X—H141X | 119.3 (9) | C15Y—C14Y—H141Y | 119.4 (10) |
C14X—C15X—C10X | 120.89 (10) | C14Y—C15Y—C10Y | 120.67 (11) |
C14X—C15X—H151X | 119.0 (9) | C14Y—C15Y—H151Y | 119.6 (9) |
C10X—C15X—H151X | 120.1 (9) | C10Y—C15Y—H151Y | 119.7 (9) |
C4X—O1X—C16X | 113.00 (9) | C16Y—O1Y—C4Y | 114.91 (9) |
O1X—C16X—H161X | 111.0 (9) | O1Y—C16Y—H161Y | 111.5 (9) |
O1X—C16X—H162X | 105.3 (10) | O1Y—C16Y—H162Y | 111.5 (9) |
H161X—C16X—H162X | 109.3 (13) | H161Y—C16Y—H162Y | 108.4 (13) |
O1X—C16X—H163X | 111.8 (10) | O1Y—C16Y—H163Y | 105.0 (10) |
H161X—C16X—H163X | 109.5 (14) | H161Y—C16Y—H163Y | 109.0 (13) |
H162X—C16X—H163X | 109.8 (14) | H162Y—C16Y—H163Y | 111.5 (14) |
| | | |
C9aX—C1X—C2X—C3X | −35.19 (11) | C9aY—C1Y—C2Y—C3Y | −35.95 (12) |
C1X—C2X—C3X—C3aX | 40.33 (11) | C1Y—C2Y—C3Y—C3aY | 42.38 (12) |
C2X—C3X—C3aX—C4X | −154.26 (9) | C2Y—C3Y—C3aY—C4Y | −157.19 (10) |
C2X—C3X—C3aX—C9aX | −29.95 (11) | C2Y—C3Y—C3aY—C9aY | −32.17 (12) |
C3X—C3aX—C4X—O1X | −73.07 (11) | C3Y—C3aY—C4Y—O1Y | −81.70 (12) |
C9aX—C3aX—C4X—O1X | 166.76 (8) | C9aY—C3aY—C4Y—O1Y | 158.24 (9) |
C3X—C3aX—C4X—C4aX | 161.53 (9) | C3Y—C3aY—C4Y—C4aY | 157.39 (10) |
C9aX—C3aX—C4X—C4aX | 41.36 (11) | C9aY—C3aY—C4Y—C4aY | 37.33 (12) |
O1X—C4X—C4aX—C5X | 6.77 (14) | O1Y—C4Y—C4aY—C5Y | 11.04 (14) |
C3aX—C4X—C4aX—C5X | 129.09 (10) | C3aY—C4Y—C4aY—C5Y | 135.38 (10) |
O1X—C4X—C4aX—C8aX | −173.95 (9) | O1Y—C4Y—C4aY—C8aY | −171.39 (9) |
C3aX—C4X—C4aX—C8aX | −51.62 (12) | C3aY—C4Y—C4aY—C8aY | −47.05 (13) |
C8aX—C4aX—C5X—C6X | −2.70 (16) | C8aY—C4aY—C5Y—C6Y | 0.39 (16) |
C4X—C4aX—C5X—C6X | 176.56 (10) | C4Y—C4aY—C5Y—C6Y | 177.91 (10) |
C4aX—C5X—C6X—C7X | −0.94 (16) | C4aY—C5Y—C6Y—C7Y | −0.53 (17) |
C5X—C6X—C7X—C8X | 3.08 (17) | C5Y—C6Y—C7Y—C8Y | 0.31 (17) |
C6X—C7X—C8X—C8aX | −1.58 (16) | C6Y—C7Y—C8Y—C8aY | 0.06 (17) |
C7X—C8X—C8aX—C4aX | −2.05 (15) | C7Y—C8Y—C8aY—C4aY | −0.20 (16) |
C7X—C8X—C8aX—C9X | 176.87 (10) | C7Y—C8Y—C8aY—C9Y | −179.97 (10) |
C5X—C4aX—C8aX—C8X | 4.17 (15) | C5Y—C4aY—C8aY—C8Y | −0.03 (15) |
C4X—C4aX—C8aX—C8X | −175.14 (9) | C4Y—C4aY—C8aY—C8Y | −177.66 (9) |
C5X—C4aX—C8aX—C9X | −174.82 (9) | C5Y—C4aY—C8aY—C9Y | 179.76 (9) |
C4X—C4aX—C8aX—C9X | 5.86 (13) | C4Y—C4aY—C8aY—C9Y | 2.12 (14) |
C8X—C8aX—C9X—C10X | −7.17 (14) | C8Y—C8aY—C9Y—C10Y | −4.42 (14) |
C4aX—C8aX—C9X—C10X | 171.77 (9) | C4aY—C8aY—C9Y—C10Y | 175.81 (9) |
C8X—C8aX—C9X—C9aX | −132.71 (10) | C8Y—C8aY—C9Y—C9aY | −130.87 (10) |
C4aX—C8aX—C9X—C9aX | 46.23 (12) | C4aY—C8aY—C9Y—C9aY | 49.35 (12) |
C10X—C9X—C9aX—C1X | 61.82 (11) | C10Y—C9Y—C9aY—C1Y | 58.49 (12) |
C8aX—C9X—C9aX—C1X | −172.34 (8) | C8aY—C9Y—C9aY—C1Y | −174.85 (9) |
C10X—C9X—C9aX—C3aX | −178.70 (8) | C10Y—C9Y—C9aY—C3aY | 178.21 (9) |
C8aX—C9X—C9aX—C3aX | −52.86 (11) | C8aY—C9Y—C9aY—C3aY | −55.13 (11) |
C2X—C1X—C9aX—C9X | 140.17 (9) | C2Y—C1Y—C9aY—C9Y | 139.17 (10) |
C2X—C1X—C9aX—C3aX | 16.56 (11) | C2Y—C1Y—C9aY—C3aY | 15.86 (12) |
C4X—C3aX—C9aX—C9X | 9.47 (12) | C4Y—C3aY—C9aY—C9Y | 12.41 (12) |
C3X—C3aX—C9aX—C9X | −115.07 (9) | C3Y—C3aY—C9aY—C9Y | −113.46 (10) |
C4X—C3aX—C9aX—C1X | 132.81 (9) | C4Y—C3aY—C9aY—C1Y | 135.91 (9) |
C3X—C3aX—C9aX—C1X | 8.27 (11) | C3Y—C3aY—C9aY—C1Y | 10.05 (11) |
C8aX—C9X—C10X—C11X | 102.86 (11) | C8aY—C9Y—C10Y—C11Y | 104.92 (11) |
C9aX—C9X—C10X—C11X | −133.38 (10) | C9aY—C9Y—C10Y—C11Y | −131.11 (11) |
C8aX—C9X—C10X—C15X | −74.96 (12) | C8aY—C9Y—C10Y—C15Y | −73.50 (13) |
C9aX—C9X—C10X—C15X | 48.80 (12) | C9aY—C9Y—C10Y—C15Y | 50.48 (13) |
C15X—C10X—C11X—C12X | −0.11 (15) | C15Y—C10Y—C11Y—C12Y | −0.17 (17) |
C9X—C10X—C11X—C12X | −177.99 (9) | C9Y—C10Y—C11Y—C12Y | −178.64 (11) |
C10X—C11X—C12X—C13X | 0.27 (16) | C10Y—C11Y—C12Y—C13Y | 0.53 (18) |
C11X—C12X—C13X—C14X | −0.22 (17) | C11Y—C12Y—C13Y—C14Y | −0.40 (19) |
C12X—C13X—C14X—C15X | 0.03 (17) | C12Y—C13Y—C14Y—C15Y | −0.08 (18) |
C13X—C14X—C15X—C10X | 0.13 (17) | C13Y—C14Y—C15Y—C10Y | 0.43 (18) |
C11X—C10X—C15X—C14X | −0.09 (15) | C11Y—C10Y—C15Y—C14Y | −0.30 (16) |
C9X—C10X—C15X—C14X | 177.77 (10) | C9Y—C10Y—C15Y—C14Y | 178.13 (10) |
C4aX—C4X—O1X—C16X | −87.95 (11) | C4aY—C4Y—O1Y—C16Y | −163.39 (9) |
C3aX—C4X—O1X—C16X | 148.01 (9) | C3aY—C4Y—O1Y—C16Y | 73.10 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9aX—H9a1X···C4aXi | 0.990 (15) | 3.109 (15) | 4.0952 (15) | 174.3 (11) |
C9aX—H9a1X···C5Xi | 0.990 (15) | 3.067 (15) | 3.9559 (15) | 150.0 (11) |
C9aX—H9a1X···C6Xi | 0.990 (15) | 3.161 (15) | 3.8645 (15) | 129.2 (10) |
C9aX—H9a1X···C7Xi | 0.990 (15) | 3.304 (15) | 3.9312 (16) | 122.9 (10) |
C9aX—H9a1X···C8Xi | 0.990 (15) | 3.301 (15) | 4.0272 (15) | 131.6 (10) |
C9aX—H9a1X···C8aXi | 0.990 (15) | 3.190 (15) | 4.0919 (15) | 152.1 (11) |
C9aX—H9a1X···CgAXi | 0.990 (15) | 2.87 | 3.74 | 147.8 |
C6X—H61X···C10Xii | 0.980 (14) | 2.974 (15) | 3.9404 (15) | 168.9 (11) |
C6X—H61X···C11Xii | 0.980 (14) | 2.861 (14) | 3.6807 (15) | 141.7 (11) |
C6X—H61X···C12Xii | 0.980 (14) | 2.986 (14) | 3.6285 (16) | 124.2 (10) |
C6X—H61X···C13Xii | 0.980 (14) | 3.212 (14) | 3.8428 (16) | 123.6 (10) |
C6X—H61X···C14Xii | 0.980 (14) | 3.304 (14) | 4.0838 (16) | 137.8 (10) |
C6X—H61X···C15Xii | 0.980 (14) | 3.185 (15) | 4.1244 (16) | 161.1 (11) |
C6X—H61X···CgDXii | 0.980 (14) | 2.76 | 3.63 | 148.3 |
C9aY—H9a1Y···C4aYiii | 0.995 (14) | 3.120 (14) | 4.1140 (15) | 178.5 (11) |
C9aY—H9a1Y···C5Yiii | 0.995 (14) | 3.066 (14) | 3.9790 (16) | 153.2 (10) |
C9aY—H9a1Y···C6Yiii | 0.995 (14) | 3.070 (14) | 3.8155 (16) | 132.7 (10) |
C9aY—H9a1Y···C7Yiii | 0.995 (14) | 3.132 (14) | 3.7971 (16) | 125.5 (9) |
C9aY—H9a1Y···C8Yiii | 0.995 (14) | 3.185 (14) | 3.9387 (15) | 133.8 (10) |
C9aY—H9a1Y···C8aYiii | 0.995 (14) | 3.183 (14) | 4.0974 (15) | 153.6 (10) |
C9aY—H9a1Y···CgAYiii | 0.995 (14) | 2.80 | 3.71 | 151.9 |
C4Y—H41Y···C4aYiv | 1.029 (14) | 2.840 (14) | 3.7503 (15) | 147.6 (10) |
C4Y—H41Y···C5Yiv | 1.029 (14) | 3.018 (14) | 4.0270 (16) | 166.8 (10) |
C4Y—H41Y···C6Yiv | 1.029 (14) | 3.417 (14) | 4.4286 (16) | 167.7 (10) |
C4Y—H41Y···C7Yiv | 1.029 (14) | 3.620 (14) | 4.5532 (16) | 151.7 (10) |
C4Y—H41Y···C8Yiv | 1.029 (14) | 3.467 (14) | 4.3041 (16) | 139.7 (10) |
C4Y—H41Y···C8aYiv | 1.029 (14) | 3.090 (14) | 3.9033 (15) | 136.7 (10) |
C4Y—H41Y···CgAYiv | 1.029 (14) | 2.94 | 3.93 | 161.8 |
C6Y—H61Y···C10Yv | 0.966 (16) | 2.983 (17) | 3.9331 (16) | 167.9 (12) |
C6Y—H61Y···C11Yv | 0.966 (16) | 2.972 (16) | 3.7786 (17) | 141.8 (12) |
C6Y—H61Y···C12Yv | 0.966 (16) | 3.002 (16) | 3.6428 (17) | 125.0 (11) |
C6Y—H61Y···C13Yv | 0.966 (16) | 3.044 (16) | 3.6687 (17) | 123.7 (11) |
C6Y—H61Y···C14Yv | 0.966 (16) | 3.040 (16) | 3.8147 (17) | 138.1 (12) |
C6Y—H61Y···C15Yv | 0.966 (16) | 3.004 (17) | 3.9375 (16) | 162.8 (12) |
C6Y—H61Y···CgDYv | 0.966 (16) | 2.67 | 3.53 | 150.0 |
C16X—H161X···C10Yiii | 1.014 (17) | 3.684 (16) | 4.4842 (18) | 137.5 (11) |
C16X—H161X···C11Yiii | 1.014 (17) | 3.770 (17) | 4.729 (2) | 158.6 (11) |
C16X—H161X···C12Yiii | 1.014 (17) | 3.543 (17) | 4.494 (2) | 157.1 (12) |
C16X—H161X···C13Yiii | 1.014 (17) | 3.177 (17) | 3.951 (2) | 134.1 (11) |
C16X—H161X···C14Yiii | 1.014 (17) | 3.050 (16) | 3.6331 (18) | 117.6 (11) |
C16X—H161X···C15Yiii | 1.014 (17) | 3.322 (16) | 3.9295 (18) | 120.1 (11) |
C16X—H161X···CgDYiii | 1.014 (17) | 3.14 | 3.99 | 141.8 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x+1, y, z. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | C21H24 | C20H22O |
Mr | 276.40 | 278.38 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 298 | 100 |
a, b, c (Å) | 9.483 (2), 11.042 (2), 9.394 (2) | 9.0001 (8), 19.287 (2), 8.9918 (8) |
α, β, γ (°) | 104.14 (2), 101.45 (2), 114.03 (2) | 96.654 (8), 101.494 (7), 97.908 (8) |
V (Å3) | 820.4 (3) | 1498.4 (2) |
Z | 2 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.06 | 0.07 |
Crystal size (mm) | 0.3 × 0.3 × 0.2 | 0.30 × 0.19 × 0.12 |
|
Data collection |
Diffractometer | Rigaku AFC-7R diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | ψ-scan (North et al., 1968) | ψ-scan North et al., 1968 |
Tmin, Tmax | 0.920, 0.987 | 0.965, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4073, 3769, 2621 | 12299, 8747, 6799 |
Rint | 0.019 | 0.016 |
(sin θ/λ)max (Å−1) | 0.650 | 0.703 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.149, 1.03 | 0.042, 0.121, 1.04 |
No. of reflections | 3769 | 8747 |
No. of parameters | 207 | 555 |
H-atom treatment | H-atom parameters constrained | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.18, −0.21 | 0.43, −0.26 |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H91···C8i | 0.98 | 3.01 | 3.848 (2) | 143.8 |
C9—H91···CgAi | 0.98 | 2.90 | 3.86 | 166.2 |
C6—H61···C14ii | 0.93 | 3.00 | 3.687 (3) | 131.4 |
C6—H61···CgDii | 0.93 | 3.04 | 3.91 | 157.4 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1. |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9aX—H9a1X···C5Xi | 0.990 (15) | 3.067 (15) | 3.9559 (15) | 150.0 (11) |
C9aX—H9a1X···CgAXi | 0.990 (15) | 2.87 | 3.74 | 147.8 |
C6X—H61X···C11Xii | 0.980 (14) | 2.861 (14) | 3.6807 (15) | 141.7 (11) |
C6X—H61X···CgDXii | 0.980 (14) | 2.76 | 3.63 | 148.3 |
C9aY—H9a1Y···C5Yiii | 0.995 (14) | 3.066 (14) | 3.9790 (16) | 153.2 (10) |
C9aY—H9a1Y···CgAYiii | 0.995 (14) | 2.80 | 3.71 | 151.9 |
C4Y—H41Y···C4aYiv | 1.029 (14) | 2.840 (14) | 3.7503 (15) | 147.6 (10) |
C4Y—H41Y···CgAYiv | 1.029 (14) | 2.94 | 3.93 | 161.8 |
C6Y—H61Y···C10Yv | 0.966 (16) | 2.983 (17) | 3.9331 (16) | 167.9 (12) |
C6Y—H61Y···CgDYv | 0.966 (16) | 2.67 | 3.53 | 150.0 |
C16X—H161X···C14Yiii | 1.014 (17) | 3.050 (16) | 3.6331 (18) | 117.6 (11) |
C16X—H161X···CgDYiii | 1.014 (17) | 3.14 | 3.99 | 141.8 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x+1, y, z. |
Photoinduced electron-transfer reactions are recognized as versatile methods for generating radical cation species from electron-rich olefins and aromatic compounds (Neunteufel & Arnold, 1973; Majima et al., 1981; Mattes & Farid, 1986; Hoffmann et al., 1993; Heinemann & Demuth, 1997). Recently, it was found that 1,1-diphenyl-1,n-alkadienes (n = 6 or 7) were converted into 5/6/6- or 6/6/6-fused ring systems with high stereoselectivity by photoirradiation in the presence of phenanthrene and 1,4-dicyanobenzene (Ishii et al., 1998). In order to elucidate the molecular geometries of the photoreaction products, X-ray structure analyses of the title compounds, (I) and (II), were carried out. Moreover, these two compounds are considered to be good candidates for examining weak intermolecular interactions, since they have no remarkable pairs of hydrogen-bonding donors or acceptors. \sch
The molecular structure of (I) is shown in Fig. 1, along with the numbering of the atoms and the abbreviations of the rings. There are no anomalous bond lengths and angles. Ring B takes a chair conformation. Ring D is bonded to ring B at the equatorial position and is arranged almost perpendicular to the fused ring moiety. The two H atoms on the bridge heads between rings B and C are axial and are trans to each other. Ring C takes an envelope conformation, with C9a as the apical atom. The stereochemistry of (I) is in good agreement with that proposed from the reaction mechanism (Ishii et al., 1998).
The crystal structure of (I) is shown in Fig. 2. There are no remarkable short contacts shorter than the sum of the van der Waals radii. This indicates that weak interactions play an important role in the formation of the crystal. Such weak interactions contribute over long distances exceeding the sum of the van der Waals radii (Dunitz, 1996). The fused-ring moieties are arranged almost parallel to the (010) plane and those in molecules which are related by the inversion centre are face-to-face with each other, forming a dimer. The C9—H91 bond is directed towards ring A and C6—H61 is directed towards ring D of adjacent molecules; the detailed geometries (Table 1) are indicative of C–H···π interactions between them (Desiraju & Gavezzotti, 1989).
The molecular structure of (II) is shown in Fig. 3. Only the structure of one molecule, labelled X in Fig. 4, of two crystallographically independent molecules is shown in Fig. 3. The structures of the independent molecules are almost the same, except for the conformations of the methoxy groups. There are no anomalous bond lengths and angles. Ring B adopts a boat conformation. The phenyl and methoxy groups are bonded to ring B at the equatorial positions to avoid steric repulsion between them and are cis with each other. The two H atoms on the bridge heads are bonded on the axial positions and are cis with each other. This leads to an envelope conformation of ring C and the apical atom C2X is exo to ring A. The stereochemistry of (II) is in good agreement with that proposed from the reaction mechanism (Ishii, 1999).
The crystal structure of (II) is shown in Fig. 4. As in the case of (I), there are no remarkable short contacts shorter than the sum of the van der Waals radii. Each independent molecule is arranged alternately along the b axis and the fused-ring systems of molecules X and Y, as shown in Fig. 4, are almost parallel to the (100) and (011) planes, respectively. Three of the possible independent C—H···π interactions are shown in Fig. 4, with full details of the geometry in Table 2.