Bianthrone [10(10-oxoanthracen-9-ylidene)anthracen-9-one] consists of two tricyclic anthraceneone units connected by a carbon-carbon double bond. Crystals of the form obtained under ambient conditions are yellow and contain folded centrosymmetric conformers in which the central ring of the anthraceneone unit is non-planar. When hydrostatic pressure is applied the crystals assume a red colouration which gradually deepens as pressures increases. The colour change is limited in extent to the surface of the crystals, the bulk remaining yellow. Comparison of high-pressure, single-crystal UV-vis spectra and powder diffraction data demonstrate that the colour change is associated with the formation of a polymorph containing a conformer in which the tricyclic fragments are planar and the molecule is twisted about the central C-C bond. Single-crystal diffraction data collected as a function of pressure up to 6.5 GPa reveal the effect of compression on the yellow form, which consists of layers of molecules which stack along the [010] direction. The structure remains in a compressed form of the ambient-pressure phase when subjected to hydrostatic pressure up to 6.5 GPa, and the most prominent effect of pressure is to push the layers closer together. PIXEL calculations show that considerable strain builds up in the crystal as pressure is increased with a number of intermolecular contacts being pushed into destabilizing regions of their potentials.
Supporting information
CCDC references: 830695; 830696; 830697; 830698; 830699; 830700; 830701; 830702
Data collection: SMART (Siemens, 1993) for ambient; USER DEFINED DATA COLLECTION for 1.2GPa, 2.2GPa, 3.3GPa, 4.2GPa, 5.1GPa, 6.0GPa, 6.5GPa. Cell refinement: SAINT (Siemens ,1995) for ambient; USER DEFINED CELL REFINEMENT for 1.2GPa, 2.2GPa, 3.3GPa, 4.2GPa, 5.1GPa, 6.0GPa, 6.5GPa. Data reduction: SAINT (Siemens ,1995) for ambient; USER DEFINED DATA REDUCTION for 1.2GPa, 2.2GPa, 3.3GPa, 4.2GPa, 5.1GPa, 6.0GPa, 6.5GPa. For all compounds, program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).
Crystal data top
C28H16O2 | F(000) = 400 |
Mr = 384.43 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3221 reflections |
a = 10.1860 (3) Å | θ = 2–28° |
b = 8.4277 (2) Å | µ = 0.08 mm−1 |
c = 11.6457 (3) Å | T = 293 K |
β = 109.591 (2)° | Block, yellow |
V = 941.85 (4) Å3 | 0.57 × 0.33 × 0.31 mm |
Z = 2 | |
Data collection top
Area diffractometer | 1867 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.049 |
ϕ & ω scans | θmax = 28.3°, θmin = 2.3° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −13→12 |
Tmin = 0.82, Tmax = 0.97 | k = 0→11 |
12386 measured reflections | l = 0→15 |
2349 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.051 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
2.33 0.420 1.55 |
S = 1.11 | (Δ/σ)max = 0.000274 |
1867 reflections | Δρmax = 0.24 e Å−3 |
136 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | |
Crystal data top
C28H16O2 | V = 941.85 (4) Å3 |
Mr = 384.43 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.1860 (3) Å | µ = 0.08 mm−1 |
b = 8.4277 (2) Å | T = 293 K |
c = 11.6457 (3) Å | 0.57 × 0.33 × 0.31 mm |
β = 109.591 (2)° | |
Data collection top
Area diffractometer | 2349 independent reflections |
Absorption correction: multi-scan SADABS (Siemens, 1996) | 1867 reflections with I > 2.0σ(I) |
Tmin = 0.82, Tmax = 0.97 | Rint = 0.049 |
12386 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.051 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.24 e Å−3 |
1867 reflections | Δρmin = −0.19 e Å−3 |
136 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.87690 (15) | 0.44936 (16) | 0.08618 (10) | 0.0623 | |
C1 | 0.89771 (18) | 0.50350 (18) | 0.18785 (12) | 0.0437 | |
C2 | 0.78803 (16) | 0.50981 (18) | 0.24506 (13) | 0.0427 | |
C3 | 0.64849 (19) | 0.5004 (2) | 0.17267 (15) | 0.0566 | |
C4 | 0.54568 (19) | 0.5310 (3) | 0.22150 (18) | 0.0644 | |
C5 | 0.58140 (19) | 0.5734 (2) | 0.34253 (18) | 0.0602 | |
C6 | 0.71879 (17) | 0.5783 (2) | 0.41644 (15) | 0.0484 | |
C7 | 0.82450 (15) | 0.54173 (17) | 0.36988 (12) | 0.0389 | |
C8 | 0.97510 (15) | 0.53666 (17) | 0.44506 (11) | 0.0363 | |
C9 | 1.06442 (15) | 0.61234 (17) | 0.38200 (12) | 0.0373 | |
C10 | 1.17792 (16) | 0.70942 (19) | 0.43993 (13) | 0.0441 | |
C11 | 1.25715 (17) | 0.7733 (2) | 0.37587 (15) | 0.0503 | |
C12 | 1.22524 (18) | 0.7417 (2) | 0.25303 (16) | 0.0533 | |
C13 | 1.11196 (17) | 0.6500 (2) | 0.19301 (14) | 0.0472 | |
C14 | 1.02917 (15) | 0.58679 (17) | 0.25589 (12) | 0.0389 | |
H1 | 0.6242 | 0.4728 | 0.0890 | 0.0648* | |
H2 | 0.4504 | 0.5229 | 0.1722 | 0.0739* | |
H3 | 0.5104 | 0.5996 | 0.3753 | 0.0737* | |
H4 | 0.7417 | 0.6070 | 0.4998 | 0.0594* | |
H5 | 1.2010 | 0.7319 | 0.5243 | 0.0531* | |
H6 | 1.3342 | 0.8395 | 0.4164 | 0.0603* | |
H7 | 1.2820 | 0.7836 | 0.2102 | 0.0678* | |
H8 | 1.0897 | 0.6295 | 0.1084 | 0.0594* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0894 (9) | 0.0643 (8) | 0.0344 (6) | −0.0150 (7) | 0.0225 (6) | −0.0111 (5) |
C1 | 0.0605 (9) | 0.0405 (8) | 0.0286 (6) | 0.0000 (7) | 0.0130 (6) | 0.0022 (5) |
C2 | 0.0503 (8) | 0.0400 (8) | 0.0340 (7) | −0.0053 (6) | 0.0091 (6) | 0.0023 (6) |
C3 | 0.0575 (10) | 0.0615 (11) | 0.0414 (8) | −0.0138 (8) | 0.0042 (7) | 0.0012 (7) |
C4 | 0.0458 (10) | 0.0685 (12) | 0.0680 (11) | −0.0089 (9) | 0.0043 (8) | 0.0047 (9) |
C5 | 0.0480 (9) | 0.0636 (11) | 0.0715 (12) | 0.0045 (9) | 0.0232 (8) | 0.0058 (9) |
C6 | 0.0484 (9) | 0.0523 (9) | 0.0455 (8) | 0.0067 (7) | 0.0172 (7) | 0.0029 (7) |
C7 | 0.0438 (8) | 0.0368 (7) | 0.0352 (7) | 0.0005 (6) | 0.0118 (6) | 0.0024 (5) |
C8 | 0.0419 (7) | 0.0406 (7) | 0.0279 (6) | 0.0006 (6) | 0.0137 (5) | −0.0040 (5) |
C9 | 0.0429 (7) | 0.0378 (7) | 0.0325 (6) | 0.0045 (6) | 0.0144 (6) | 0.0024 (5) |
C10 | 0.0493 (8) | 0.0454 (8) | 0.0369 (7) | −0.0001 (7) | 0.0134 (6) | −0.0005 (6) |
C11 | 0.0468 (9) | 0.0500 (9) | 0.0525 (9) | −0.0055 (7) | 0.0146 (7) | 0.0025 (7) |
C12 | 0.0562 (10) | 0.0567 (10) | 0.0552 (9) | −0.0006 (8) | 0.0295 (8) | 0.0093 (8) |
C13 | 0.0598 (10) | 0.0501 (9) | 0.0368 (7) | 0.0058 (8) | 0.0230 (7) | 0.0040 (6) |
C14 | 0.0471 (8) | 0.0392 (7) | 0.0317 (6) | 0.0045 (6) | 0.0149 (6) | 0.0028 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.2193 (17) | C7—C8 | 1.490 (2) |
C1—C2 | 1.481 (2) | C8—C8i | 1.357 (3) |
C1—C14 | 1.484 (2) | C8—C9 | 1.4907 (19) |
C2—C3 | 1.391 (2) | C9—C10 | 1.392 (2) |
C2—C7 | 1.4004 (19) | C9—C14 | 1.4066 (19) |
C3—C4 | 1.373 (3) | C10—C11 | 1.379 (2) |
C3—H1 | 0.950 | C10—H5 | 0.950 |
C4—C5 | 1.380 (3) | C11—C12 | 1.382 (2) |
C4—H2 | 0.950 | C11—H6 | 0.950 |
C5—C6 | 1.376 (2) | C12—C13 | 1.370 (2) |
C5—H3 | 0.950 | C12—H7 | 0.950 |
C6—C7 | 1.393 (2) | C13—C14 | 1.395 (2) |
C6—H4 | 0.950 | C13—H8 | 0.950 |
| | | |
O1—C1—C2 | 122.58 (15) | C7—C8—C8i | 123.56 (16) |
O1—C1—C14 | 121.83 (15) | C7—C8—C9 | 112.11 (11) |
C2—C1—C14 | 115.12 (12) | C8i—C8—C9 | 124.23 (16) |
C1—C2—C3 | 119.80 (14) | C8—C9—C10 | 123.89 (12) |
C1—C2—C7 | 119.75 (13) | C8—C9—C14 | 117.69 (13) |
C3—C2—C7 | 120.12 (15) | C10—C9—C14 | 118.41 (13) |
C2—C3—C4 | 120.30 (16) | C9—C10—C11 | 120.59 (14) |
C2—C3—H1 | 119.8 | C9—C10—H5 | 119.7 |
C4—C3—H1 | 119.9 | C11—C10—H5 | 119.7 |
C3—C4—C5 | 119.69 (16) | C10—C11—C12 | 120.49 (16) |
C3—C4—H2 | 120.2 | C10—C11—H6 | 119.8 |
C5—C4—H2 | 120.2 | C12—C11—H6 | 119.7 |
C4—C5—C6 | 120.76 (17) | C11—C12—C13 | 120.15 (15) |
C4—C5—H3 | 119.7 | C11—C12—H7 | 119.9 |
C6—C5—H3 | 119.6 | C13—C12—H7 | 119.9 |
C5—C6—C7 | 120.45 (16) | C12—C13—C14 | 120.12 (14) |
C5—C6—H4 | 119.8 | C12—C13—H8 | 120.0 |
C7—C6—H4 | 119.8 | C14—C13—H8 | 119.9 |
C2—C7—C6 | 118.42 (14) | C1—C14—C9 | 119.91 (13) |
C2—C7—C8 | 117.83 (13) | C1—C14—C13 | 119.77 (13) |
C6—C7—C8 | 123.74 (13) | C9—C14—C13 | 120.14 (14) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C28H16O2 | F(000) = 400 |
Mr = 384.43 | Dx = 1.500 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
Hall symbol: -P 2yn | Cell parameters from 991 reflections |
a = 9.9825 (11) Å | θ = 4–15° |
b = 7.8892 (15) Å | µ = 0.09 mm−1 |
c = 11.4879 (9) Å | T = 293 K |
β = 109.780 (6)° | Block, yellow |
V = 851.3 (2) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Serial diffractometer | 644 reflections with I > 2.0σ(I) |
Silicon monochromator | Rint = 0.087 |
ω scans | θmax = 15.4°, θmin = 2.2° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −10→10 |
Tmin = 0.86, Tmax = 0.99 | k = 0→6 |
4044 measured reflections | l = 0→12 |
852 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.044 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
10.6 -10.4 5.69 |
S = 1.01 | (Δ/σ)max = 0.000280 |
644 reflections | Δρmax = 0.12 e Å−3 |
136 parameters | Δρmin = −0.13 e Å−3 |
187 restraints | |
Crystal data top
C28H16O2 | V = 851.3 (2) Å3 |
Mr = 384.43 | Z = 2 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
a = 9.9825 (11) Å | µ = 0.09 mm−1 |
b = 7.8892 (15) Å | T = 293 K |
c = 11.4879 (9) Å | 0.20 × 0.20 × 0.10 mm |
β = 109.780 (6)° | |
Data collection top
Serial diffractometer | 852 independent reflections |
Absorption correction: multi-scan SADABS (Siemens, 1996) | 644 reflections with I > 2.0σ(I) |
Tmin = 0.86, Tmax = 0.99 | Rint = 0.087 |
4044 measured reflections | θmax = 15.4° |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 187 restraints |
wR(F2) = 0.044 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.12 e Å−3 |
644 reflections | Δρmin = −0.13 e Å−3 |
136 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.86692 (17) | 0.4527 (3) | 0.07791 (13) | 0.0397 | |
C1 | 0.8906 (2) | 0.5083 (4) | 0.18235 (16) | 0.0266 | |
C2 | 0.7805 (2) | 0.5147 (4) | 0.24152 (17) | 0.0272 | |
C3 | 0.6372 (2) | 0.5081 (4) | 0.16861 (18) | 0.0344 | |
C4 | 0.5339 (2) | 0.5399 (5) | 0.2190 (2) | 0.0388 | |
C5 | 0.5720 (2) | 0.5803 (4) | 0.3428 (2) | 0.0385 | |
C6 | 0.7131 (2) | 0.5842 (4) | 0.41712 (18) | 0.0329 | |
C7 | 0.8197 (2) | 0.5461 (4) | 0.36861 (16) | 0.0248 | |
C8 | 0.9743 (2) | 0.5382 (4) | 0.44409 (15) | 0.0243 | |
C9 | 1.0648 (2) | 0.6191 (4) | 0.37900 (16) | 0.0262 | |
C10 | 1.1844 (2) | 0.7159 (4) | 0.43727 (18) | 0.0291 | |
C11 | 1.2648 (2) | 0.7829 (4) | 0.37240 (19) | 0.0326 | |
C12 | 1.2272 (2) | 0.7545 (4) | 0.24690 (19) | 0.0341 | |
C13 | 1.1078 (2) | 0.6637 (4) | 0.18575 (17) | 0.0317 | |
C14 | 1.0253 (2) | 0.5946 (4) | 0.25055 (16) | 0.0239 | |
H1 | 0.6111 | 0.4814 | 0.0832 | 0.0396* | |
H2 | 0.4363 | 0.5342 | 0.1690 | 0.0432* | |
H3 | 0.5002 | 0.6062 | 0.3771 | 0.0467* | |
H4 | 0.7377 | 0.6125 | 0.5022 | 0.0400* | |
H5 | 1.2114 | 0.7359 | 0.5237 | 0.0348* | |
H6 | 1.3465 | 0.8490 | 0.4141 | 0.0379* | |
H7 | 1.2849 | 0.7984 | 0.2029 | 0.0426* | |
H8 | 1.0806 | 0.6480 | 0.0988 | 0.0382* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0533 (13) | 0.043 (2) | 0.0218 (8) | −0.0043 (9) | 0.0116 (7) | −0.0038 (8) |
C1 | 0.0380 (13) | 0.021 (3) | 0.0200 (10) | 0.0022 (10) | 0.0087 (8) | 0.0045 (10) |
C2 | 0.0341 (11) | 0.021 (3) | 0.0249 (10) | −0.0024 (10) | 0.0078 (8) | 0.0039 (11) |
C3 | 0.0360 (12) | 0.033 (3) | 0.0293 (11) | −0.0054 (12) | 0.0046 (8) | 0.0022 (12) |
C4 | 0.0286 (13) | 0.033 (3) | 0.0497 (12) | −0.0058 (11) | 0.0070 (9) | 0.0011 (14) |
C5 | 0.0313 (12) | 0.038 (3) | 0.0495 (12) | 0.0010 (12) | 0.0185 (9) | 0.0034 (15) |
C6 | 0.0355 (12) | 0.032 (3) | 0.0336 (12) | 0.0041 (11) | 0.0148 (8) | 0.0023 (13) |
C7 | 0.0322 (11) | 0.017 (3) | 0.0252 (10) | −0.0009 (10) | 0.0095 (8) | 0.0014 (11) |
C8 | 0.0314 (12) | 0.023 (3) | 0.0194 (9) | −0.0001 (10) | 0.0099 (8) | −0.0036 (11) |
C9 | 0.0284 (13) | 0.029 (3) | 0.0226 (9) | 0.0048 (10) | 0.0102 (8) | 0.0026 (11) |
C10 | 0.0320 (14) | 0.031 (3) | 0.0244 (11) | 0.0037 (10) | 0.0093 (8) | 0.0009 (11) |
C11 | 0.0292 (14) | 0.033 (3) | 0.0355 (11) | −0.0029 (11) | 0.0101 (9) | 0.0019 (12) |
C12 | 0.0313 (15) | 0.042 (3) | 0.0356 (10) | 0.0005 (10) | 0.0198 (9) | 0.0036 (12) |
C13 | 0.0338 (15) | 0.040 (3) | 0.0244 (11) | 0.0048 (10) | 0.0141 (9) | 0.0022 (12) |
C14 | 0.0330 (13) | 0.015 (3) | 0.0232 (9) | 0.0062 (9) | 0.0096 (8) | 0.0048 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.223 (2) | C7—C8 | 1.493 (3) |
C1—C2 | 1.476 (3) | C8—C8i | 1.353 (4) |
C1—C14 | 1.474 (3) | C8—C9 | 1.497 (3) |
C2—C3 | 1.393 (3) | C9—C10 | 1.384 (3) |
C2—C7 | 1.400 (3) | C9—C14 | 1.406 (2) |
C3—C4 | 1.366 (3) | C10—C11 | 1.372 (3) |
C3—H1 | 0.950 | C10—H5 | 0.950 |
C4—C5 | 1.378 (3) | C11—C12 | 1.380 (3) |
C4—H2 | 0.950 | C11—H6 | 0.950 |
C5—C6 | 1.379 (3) | C12—C13 | 1.364 (3) |
C5—H3 | 0.950 | C12—H7 | 0.950 |
C6—C7 | 1.391 (3) | C13—C14 | 1.394 (3) |
C6—H4 | 0.950 | C13—H8 | 0.950 |
| | | |
O1—C1—C2 | 122.51 (17) | C7—C8—C8i | 123.8 (3) |
O1—C1—C14 | 121.69 (17) | C7—C8—C9 | 111.83 (16) |
C2—C1—C14 | 115.29 (16) | C8i—C8—C9 | 124.4 (2) |
C1—C2—C3 | 119.68 (16) | C8—C9—C10 | 124.15 (16) |
C1—C2—C7 | 119.81 (15) | C8—C9—C14 | 117.62 (17) |
C3—C2—C7 | 120.13 (17) | C10—C9—C14 | 118.23 (17) |
C2—C3—C4 | 120.47 (18) | C9—C10—C11 | 121.13 (17) |
C2—C3—H1 | 119.7 | C9—C10—H5 | 119.4 |
C4—C3—H1 | 119.8 | C11—C10—H5 | 119.5 |
C3—C4—C5 | 119.68 (18) | C10—C11—C12 | 120.19 (19) |
C3—C4—H2 | 120.1 | C10—C11—H6 | 119.8 |
C5—C4—H2 | 120.2 | C12—C11—H6 | 120.0 |
C4—C5—C6 | 120.78 (19) | C11—C12—C13 | 120.29 (18) |
C4—C5—H3 | 119.6 | C11—C12—H7 | 119.8 |
C6—C5—H3 | 119.6 | C13—C12—H7 | 119.9 |
C5—C6—C7 | 120.45 (18) | C12—C13—C14 | 120.09 (17) |
C5—C6—H4 | 119.8 | C12—C13—H8 | 119.9 |
C7—C6—H4 | 119.8 | C14—C13—H8 | 120.0 |
C2—C7—C6 | 118.29 (16) | C1—C14—C9 | 120.17 (15) |
C2—C7—C8 | 117.90 (16) | C1—C14—C13 | 119.62 (15) |
C6—C7—C8 | 123.80 (16) | C9—C14—C13 | 120.01 (17) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C28H16O2 | F(000) = 400 |
Mr = 384.43 | Dx = 1.568 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
Hall symbol: -P 2yn | Cell parameters from 1079 reflections |
a = 9.9021 (14) Å | θ = 3–15° |
b = 7.6543 (18) Å | µ = 0.10 mm−1 |
c = 11.4225 (11) Å | T = 293 K |
β = 109.860 (9)° | Block, yellow |
V = 814.3 (2) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Serial diffractometer | 625 reflections with I > 2.0σ(I) |
Silicon monochromator | Rint = 0.087 |
ω scans | θmax = 15.5°, θmin = 1.6° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −10→10 |
Tmin = 0.78, Tmax = 0.99 | k = 0→6 |
3792 measured reflections | l = 0→12 |
818 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.047 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
12.9 -12.1 8.54 |
S = 1.04 | (Δ/σ)max = 0.000227 |
625 reflections | Δρmax = 0.15 e Å−3 |
136 parameters | Δρmin = −0.15 e Å−3 |
187 restraints | |
Crystal data top
C28H16O2 | V = 814.3 (2) Å3 |
Mr = 384.43 | Z = 2 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
a = 9.9021 (14) Å | µ = 0.10 mm−1 |
b = 7.6543 (18) Å | T = 293 K |
c = 11.4225 (11) Å | 0.20 × 0.20 × 0.10 mm |
β = 109.860 (9)° | |
Data collection top
Serial diffractometer | 818 independent reflections |
Absorption correction: multi-scan SADABS (Siemens, 1996) | 625 reflections with I > 2.0σ(I) |
Tmin = 0.78, Tmax = 0.99 | Rint = 0.087 |
3792 measured reflections | θmax = 15.5° |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | 187 restraints |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.15 e Å−3 |
625 reflections | Δρmin = −0.15 e Å−3 |
136 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.86321 (17) | 0.4528 (3) | 0.07419 (14) | 0.0332 | |
C1 | 0.8877 (2) | 0.5103 (4) | 0.17949 (17) | 0.0243 | |
C2 | 0.7776 (2) | 0.5166 (4) | 0.23946 (18) | 0.0241 | |
C3 | 0.6331 (2) | 0.5105 (4) | 0.16595 (19) | 0.0287 | |
C4 | 0.5292 (2) | 0.5445 (5) | 0.2173 (2) | 0.0339 | |
C5 | 0.5684 (2) | 0.5827 (4) | 0.3421 (2) | 0.0334 | |
C6 | 0.7100 (2) | 0.5844 (4) | 0.4168 (2) | 0.0280 | |
C7 | 0.8177 (2) | 0.5480 (4) | 0.36758 (18) | 0.0235 | |
C8 | 0.9737 (2) | 0.5381 (4) | 0.44335 (17) | 0.0243 | |
C9 | 1.0652 (2) | 0.6194 (4) | 0.37746 (18) | 0.0217 | |
C10 | 1.1873 (2) | 0.7198 (4) | 0.43661 (18) | 0.0252 | |
C11 | 1.2678 (2) | 0.7872 (4) | 0.3705 (2) | 0.0286 | |
C12 | 1.2275 (2) | 0.7619 (4) | 0.2434 (2) | 0.0289 | |
C13 | 1.1055 (2) | 0.6697 (4) | 0.1819 (2) | 0.0265 | |
C14 | 1.0231 (2) | 0.5986 (4) | 0.24753 (18) | 0.0213 | |
H1 | 0.6065 | 0.4826 | 0.0800 | 0.0324* | |
H2 | 0.4307 | 0.5418 | 0.1669 | 0.0390* | |
H3 | 0.4962 | 0.6084 | 0.3771 | 0.0413* | |
H4 | 0.7348 | 0.6106 | 0.5028 | 0.0346* | |
H5 | 1.2148 | 0.7417 | 0.5235 | 0.0297* | |
H6 | 1.3523 | 0.8520 | 0.4125 | 0.0342* | |
H7 | 1.2845 | 0.8085 | 0.1986 | 0.0368* | |
H8 | 1.0769 | 0.6543 | 0.0944 | 0.0334* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0427 (12) | 0.036 (2) | 0.0203 (8) | −0.0034 (8) | 0.0098 (7) | −0.0031 (8) |
C1 | 0.0281 (13) | 0.025 (3) | 0.0176 (11) | 0.0018 (10) | 0.0052 (8) | 0.0034 (11) |
C2 | 0.0279 (11) | 0.022 (2) | 0.0217 (10) | −0.0032 (10) | 0.0071 (8) | 0.0033 (12) |
C3 | 0.0306 (12) | 0.024 (3) | 0.0264 (12) | −0.0039 (11) | 0.0029 (8) | 0.0024 (13) |
C4 | 0.0246 (14) | 0.030 (3) | 0.0422 (13) | −0.0071 (11) | 0.0056 (10) | 0.0010 (14) |
C5 | 0.0294 (13) | 0.031 (3) | 0.0429 (13) | 0.0026 (12) | 0.0163 (10) | 0.0023 (15) |
C6 | 0.0325 (12) | 0.027 (3) | 0.0273 (13) | 0.0040 (11) | 0.0133 (9) | 0.0004 (13) |
C7 | 0.0246 (11) | 0.022 (2) | 0.0237 (10) | −0.0021 (11) | 0.0076 (8) | 0.0002 (12) |
C8 | 0.0256 (12) | 0.032 (3) | 0.0164 (10) | 0.0001 (11) | 0.0082 (8) | −0.0046 (12) |
C9 | 0.0248 (13) | 0.020 (2) | 0.0205 (10) | 0.0047 (9) | 0.0081 (8) | 0.0018 (12) |
C10 | 0.0284 (14) | 0.029 (3) | 0.0171 (11) | 0.0014 (10) | 0.0060 (9) | −0.0029 (12) |
C11 | 0.0281 (14) | 0.029 (3) | 0.0284 (11) | 0.0014 (11) | 0.0092 (9) | 0.0036 (13) |
C12 | 0.0289 (14) | 0.034 (3) | 0.0286 (11) | 0.0008 (11) | 0.0163 (9) | 0.0044 (13) |
C13 | 0.0312 (15) | 0.030 (3) | 0.0227 (12) | 0.0040 (10) | 0.0143 (9) | −0.0001 (12) |
C14 | 0.0230 (13) | 0.021 (3) | 0.0207 (10) | 0.0060 (9) | 0.0084 (8) | −0.0005 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.225 (2) | C7—C8 | 1.494 (3) |
C1—C2 | 1.473 (3) | C8—C8i | 1.352 (4) |
C1—C14 | 1.466 (3) | C8—C9 | 1.496 (3) |
C2—C3 | 1.392 (3) | C9—C10 | 1.399 (3) |
C2—C7 | 1.401 (3) | C9—C14 | 1.408 (3) |
C3—C4 | 1.371 (3) | C10—C11 | 1.371 (3) |
C3—H1 | 0.950 | C10—H5 | 0.950 |
C4—C5 | 1.376 (3) | C11—C12 | 1.383 (3) |
C4—H2 | 0.950 | C11—H6 | 0.950 |
C5—C6 | 1.372 (3) | C12—C13 | 1.369 (3) |
C5—H3 | 0.950 | C12—H7 | 0.950 |
C6—C7 | 1.392 (3) | C13—C14 | 1.392 (3) |
C6—H4 | 0.950 | C13—H8 | 0.950 |
| | | |
O1—C1—C2 | 122.50 (17) | C7—C8—C8i | 124.2 (3) |
O1—C1—C14 | 121.78 (17) | C7—C8—C9 | 111.79 (17) |
C2—C1—C14 | 115.24 (17) | C8i—C8—C9 | 124.0 (2) |
C1—C2—C3 | 119.35 (16) | C8—C9—C10 | 123.91 (17) |
C1—C2—C7 | 119.97 (16) | C8—C9—C14 | 118.09 (17) |
C3—C2—C7 | 120.30 (16) | C10—C9—C14 | 117.96 (17) |
C2—C3—C4 | 120.16 (19) | C9—C10—C11 | 120.66 (18) |
C2—C3—H1 | 119.9 | C9—C10—H5 | 119.7 |
C4—C3—H1 | 119.9 | C11—C10—H5 | 119.7 |
C3—C4—C5 | 119.71 (19) | C10—C11—C12 | 120.74 (19) |
C3—C4—H2 | 120.1 | C10—C11—H6 | 119.6 |
C5—C4—H2 | 120.1 | C12—C11—H6 | 119.6 |
C4—C5—C6 | 120.98 (19) | C11—C12—C13 | 119.99 (19) |
C4—C5—H3 | 119.5 | C11—C12—H7 | 120.0 |
C6—C5—H3 | 119.5 | C13—C12—H7 | 120.0 |
C5—C6—C7 | 120.57 (18) | C12—C13—C14 | 120.16 (18) |
C5—C6—H4 | 119.7 | C12—C13—H8 | 119.9 |
C7—C6—H4 | 119.7 | C14—C13—H8 | 119.9 |
C2—C7—C6 | 118.16 (16) | C1—C14—C9 | 120.04 (16) |
C2—C7—C8 | 117.84 (16) | C1—C14—C13 | 119.49 (16) |
C6—C7—C8 | 124.00 (17) | C9—C14—C13 | 120.38 (17) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C28H16O2 | F(000) = 400 |
Mr = 384.43 | Dx = 1.631 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
Hall symbol: -P 2yn | Cell parameters from 936 reflections |
a = 9.8354 (13) Å | θ = 2–15° |
b = 7.4567 (19) Å | µ = 0.10 mm−1 |
c = 11.3543 (12) Å | T = 293 K |
β = 109.939 (8)° | Block, yellow |
V = 782.8 (2) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Serial diffractometer | 583 reflections with I > 2.0σ(I) |
Silicon monochromator | Rint = 0.093 |
ω scans | θmax = 15.5°, θmin = 2.3° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −10→10 |
Tmin = 0.84, Tmax = 0.99 | k = 0→6 |
3798 measured reflections | l = 0→12 |
772 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.043 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
7.77 -6.06 4.02 |
S = 1.04 | (Δ/σ)max = 0.000179 |
583 reflections | Δρmax = 0.15 e Å−3 |
136 parameters | Δρmin = −0.16 e Å−3 |
187 restraints | |
Crystal data top
C28H16O2 | V = 782.8 (2) Å3 |
Mr = 384.43 | Z = 2 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
a = 9.8354 (13) Å | µ = 0.10 mm−1 |
b = 7.4567 (19) Å | T = 293 K |
c = 11.3543 (12) Å | 0.20 × 0.20 × 0.10 mm |
β = 109.939 (8)° | |
Data collection top
Serial diffractometer | 772 independent reflections |
Absorption correction: multi-scan SADABS (Siemens, 1996) | 583 reflections with I > 2.0σ(I) |
Tmin = 0.84, Tmax = 0.99 | Rint = 0.093 |
3798 measured reflections | θmax = 15.5° |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 187 restraints |
wR(F2) = 0.043 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.15 e Å−3 |
583 reflections | Δρmin = −0.16 e Å−3 |
136 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.85998 (17) | 0.4526 (3) | 0.07124 (15) | 0.0318 | |
C1 | 0.8853 (2) | 0.5109 (5) | 0.17693 (18) | 0.0220 | |
C2 | 0.7752 (2) | 0.5175 (5) | 0.23780 (19) | 0.0222 | |
C3 | 0.6299 (2) | 0.5136 (5) | 0.1634 (2) | 0.0269 | |
C4 | 0.5251 (2) | 0.5479 (5) | 0.2143 (2) | 0.0335 | |
C5 | 0.5650 (2) | 0.5829 (5) | 0.3404 (2) | 0.0340 | |
C6 | 0.7086 (2) | 0.5841 (5) | 0.4161 (2) | 0.0254 | |
C7 | 0.8160 (2) | 0.5476 (4) | 0.36688 (19) | 0.0183 | |
C8 | 0.9732 (2) | 0.5381 (4) | 0.44259 (17) | 0.0216 | |
C9 | 1.0652 (2) | 0.6216 (4) | 0.37616 (19) | 0.0208 | |
C10 | 1.1898 (2) | 0.7200 (5) | 0.4355 (2) | 0.0239 | |
C11 | 1.2704 (2) | 0.7892 (5) | 0.3685 (2) | 0.0256 | |
C12 | 1.2274 (2) | 0.7678 (5) | 0.2406 (2) | 0.0283 | |
C13 | 1.1037 (2) | 0.6767 (5) | 0.1788 (2) | 0.0259 | |
C14 | 1.0220 (2) | 0.6018 (4) | 0.24527 (18) | 0.0211 | |
H1 | 0.6033 | 0.4867 | 0.0766 | 0.0294* | |
H2 | 0.4260 | 0.5481 | 0.1631 | 0.0374* | |
H3 | 0.4924 | 0.6063 | 0.3761 | 0.0425* | |
H4 | 0.7337 | 0.6103 | 0.5028 | 0.0306* | |
H5 | 1.2198 | 0.7390 | 0.5234 | 0.0268* | |
H6 | 1.3565 | 0.8537 | 0.4109 | 0.0302* | |
H7 | 1.2844 | 0.8161 | 0.1954 | 0.0343* | |
H8 | 1.0727 | 0.6646 | 0.0903 | 0.0310* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0377 (11) | 0.040 (2) | 0.0173 (8) | −0.0005 (9) | 0.0083 (7) | −0.0013 (10) |
C1 | 0.0297 (13) | 0.019 (3) | 0.0161 (11) | 0.0035 (11) | 0.0062 (9) | 0.0048 (12) |
C2 | 0.0254 (11) | 0.018 (3) | 0.0217 (11) | −0.0023 (12) | 0.0065 (8) | 0.0006 (13) |
C3 | 0.0287 (12) | 0.024 (3) | 0.0227 (13) | −0.0083 (13) | 0.0019 (9) | −0.0003 (15) |
C4 | 0.0222 (13) | 0.033 (3) | 0.0395 (13) | −0.0053 (13) | 0.0034 (10) | 0.0024 (17) |
C5 | 0.0253 (12) | 0.038 (4) | 0.0416 (13) | 0.0010 (13) | 0.0158 (10) | 0.0031 (17) |
C6 | 0.0291 (12) | 0.024 (3) | 0.0239 (13) | 0.0041 (12) | 0.0102 (9) | 0.0035 (14) |
C7 | 0.0248 (11) | 0.007 (3) | 0.0233 (10) | −0.0026 (11) | 0.0084 (8) | 0.0018 (14) |
C8 | 0.0226 (11) | 0.028 (3) | 0.0157 (10) | −0.0015 (11) | 0.0087 (8) | −0.0073 (13) |
C9 | 0.0222 (13) | 0.022 (3) | 0.0186 (10) | 0.0047 (10) | 0.0068 (9) | 0.0041 (12) |
C10 | 0.0276 (14) | 0.025 (3) | 0.0173 (11) | 0.0027 (11) | 0.0058 (9) | 0.0004 (13) |
C11 | 0.0260 (14) | 0.021 (3) | 0.0294 (12) | −0.0024 (12) | 0.0084 (10) | −0.0018 (14) |
C12 | 0.0206 (13) | 0.042 (3) | 0.0267 (11) | 0.0014 (12) | 0.0136 (10) | 0.0077 (14) |
C13 | 0.0284 (14) | 0.033 (3) | 0.0189 (12) | 0.0030 (11) | 0.0116 (9) | −0.0022 (13) |
C14 | 0.0228 (13) | 0.022 (3) | 0.0177 (10) | 0.0069 (10) | 0.0064 (9) | 0.0040 (13) |
Geometric parameters (Å, º) top
O1—C1 | 1.220 (3) | C7—C8 | 1.493 (3) |
C1—C2 | 1.471 (3) | C8—C8i | 1.354 (4) |
C1—C14 | 1.469 (3) | C8—C9 | 1.497 (3) |
C2—C3 | 1.391 (3) | C9—C10 | 1.390 (3) |
C2—C7 | 1.399 (3) | C9—C14 | 1.407 (3) |
C3—C4 | 1.367 (3) | C10—C11 | 1.373 (3) |
C3—H1 | 0.950 | C10—H5 | 0.950 |
C4—C5 | 1.374 (3) | C11—C12 | 1.376 (3) |
C4—H2 | 0.950 | C11—H6 | 0.950 |
C5—C6 | 1.380 (3) | C12—C13 | 1.361 (4) |
C5—H3 | 0.950 | C12—H7 | 0.950 |
C6—C7 | 1.380 (3) | C13—C14 | 1.392 (3) |
C6—H4 | 0.950 | C13—H8 | 0.950 |
| | | |
O1—C1—C2 | 122.54 (18) | C7—C8—C8i | 124.1 (3) |
O1—C1—C14 | 121.84 (17) | C7—C8—C9 | 112.07 (17) |
C2—C1—C14 | 115.12 (17) | C8i—C8—C9 | 123.8 (2) |
C1—C2—C3 | 118.85 (17) | C8—C9—C10 | 124.05 (17) |
C1—C2—C7 | 120.21 (16) | C8—C9—C14 | 118.14 (18) |
C3—C2—C7 | 120.55 (16) | C10—C9—C14 | 117.80 (17) |
C2—C3—C4 | 120.36 (19) | C9—C10—C11 | 120.65 (18) |
C2—C3—H1 | 119.8 | C9—C10—H5 | 119.6 |
C4—C3—H1 | 119.8 | C11—C10—H5 | 119.7 |
C3—C4—C5 | 119.23 (19) | C10—C11—C12 | 120.9 (2) |
C3—C4—H2 | 120.4 | C10—C11—H6 | 119.5 |
C5—C4—H2 | 120.4 | C12—C11—H6 | 119.5 |
C4—C5—C6 | 121.16 (19) | C11—C12—C13 | 119.99 (19) |
C4—C5—H3 | 119.4 | C11—C12—H7 | 120.0 |
C6—C5—H3 | 119.4 | C13—C12—H7 | 120.0 |
C5—C6—C7 | 120.58 (19) | C12—C13—C14 | 120.05 (18) |
C5—C6—H4 | 119.7 | C12—C13—H8 | 120.0 |
C7—C6—H4 | 119.7 | C14—C13—H8 | 120.0 |
C2—C7—C6 | 118.01 (16) | C1—C14—C9 | 119.92 (16) |
C2—C7—C8 | 117.80 (16) | C1—C14—C13 | 119.46 (17) |
C6—C7—C8 | 124.19 (18) | C9—C14—C13 | 120.52 (18) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C28H16O2 | F(000) = 400 |
Mr = 384.43 | Dx = 1.683 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
Hall symbol: -P 2yn | Cell parameters from 1122 reflections |
a = 9.7854 (7) Å | θ = 3–15° |
b = 7.2988 (11) Å | µ = 0.11 mm−1 |
c = 11.3074 (7) Å | T = 293 K |
β = 110.028 (4)° | Block, yellow |
V = 758.75 (14) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Serial diffractometer | 554 reflections with I > 2.0σ(I) |
Silicon monochromator | Rint = 0.074 |
ω scans | θmax = 15.4°, θmin = 3.0° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −10→10 |
Tmin = 0.84, Tmax = 0.99 | k = 0→5 |
3269 measured reflections | l = 0→12 |
689 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.044 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
13.2 -13.0 7.93 |
S = 1.07 | (Δ/σ)max = 0.000230 |
554 reflections | Δρmax = 0.16 e Å−3 |
136 parameters | Δρmin = −0.16 e Å−3 |
187 restraints | |
Crystal data top
C28H16O2 | V = 758.75 (14) Å3 |
Mr = 384.43 | Z = 2 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
a = 9.7854 (7) Å | µ = 0.11 mm−1 |
b = 7.2988 (11) Å | T = 293 K |
c = 11.3074 (7) Å | 0.20 × 0.20 × 0.10 mm |
β = 110.028 (4)° | |
Data collection top
Serial diffractometer | 689 independent reflections |
Absorption correction: multi-scan SADABS (Siemens, 1996) | 554 reflections with I > 2.0σ(I) |
Tmin = 0.84, Tmax = 0.99 | Rint = 0.074 |
3269 measured reflections | θmax = 15.4° |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 187 restraints |
wR(F2) = 0.044 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.16 e Å−3 |
554 reflections | Δρmin = −0.16 e Å−3 |
136 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.85799 (15) | 0.4518 (3) | 0.06830 (13) | 0.0277 | |
C1 | 0.8837 (2) | 0.5106 (4) | 0.17486 (16) | 0.0212 | |
C2 | 0.77342 (18) | 0.5187 (5) | 0.23608 (17) | 0.0210 | |
C3 | 0.6271 (2) | 0.5170 (5) | 0.16074 (19) | 0.0258 | |
C4 | 0.5223 (2) | 0.5514 (5) | 0.2120 (2) | 0.0285 | |
C5 | 0.5626 (2) | 0.5845 (5) | 0.3396 (2) | 0.0308 | |
C6 | 0.7066 (2) | 0.5848 (5) | 0.41546 (18) | 0.0272 | |
C7 | 0.81505 (19) | 0.5482 (4) | 0.36579 (17) | 0.0186 | |
C8 | 0.9729 (2) | 0.5384 (4) | 0.44205 (16) | 0.0200 | |
C9 | 1.0651 (2) | 0.6232 (4) | 0.37471 (16) | 0.0220 | |
C10 | 1.1911 (2) | 0.7221 (5) | 0.43416 (17) | 0.0210 | |
C11 | 1.2723 (2) | 0.7916 (5) | 0.36745 (18) | 0.0224 | |
C12 | 1.2270 (2) | 0.7713 (5) | 0.23783 (19) | 0.0268 | |
C13 | 1.1013 (2) | 0.6805 (5) | 0.17590 (18) | 0.0238 | |
C14 | 1.02043 (19) | 0.6035 (4) | 0.24345 (16) | 0.0223 | |
H1 | 0.6003 | 0.4915 | 0.0733 | 0.0287* | |
H2 | 0.4226 | 0.5525 | 0.1604 | 0.0322* | |
H3 | 0.4897 | 0.6077 | 0.3756 | 0.0388* | |
H4 | 0.7320 | 0.6104 | 0.5027 | 0.0326* | |
H5 | 1.2213 | 0.7418 | 0.5224 | 0.0262* | |
H6 | 1.3606 | 0.8539 | 0.4103 | 0.0263* | |
H7 | 1.2837 | 0.8210 | 0.1922 | 0.0344* | |
H8 | 1.0689 | 0.6698 | 0.0868 | 0.0292* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0369 (9) | 0.027 (2) | 0.0185 (7) | −0.0033 (8) | 0.0085 (6) | −0.0039 (8) |
C1 | 0.0288 (11) | 0.020 (3) | 0.0142 (9) | 0.0035 (10) | 0.0065 (8) | 0.0046 (11) |
C2 | 0.0242 (10) | 0.016 (3) | 0.0219 (10) | −0.0010 (11) | 0.0067 (8) | 0.0018 (12) |
C3 | 0.0276 (10) | 0.022 (3) | 0.0226 (11) | −0.0071 (12) | 0.0020 (8) | 0.0018 (13) |
C4 | 0.0231 (11) | 0.018 (3) | 0.0405 (11) | −0.0047 (12) | 0.0055 (9) | 0.0016 (15) |
C5 | 0.0240 (11) | 0.030 (4) | 0.0410 (11) | 0.0010 (12) | 0.0151 (9) | 0.0029 (15) |
C6 | 0.0266 (11) | 0.032 (4) | 0.0241 (11) | 0.0038 (12) | 0.0108 (8) | 0.0041 (14) |
C7 | 0.0237 (10) | 0.010 (3) | 0.0221 (9) | −0.0003 (10) | 0.0081 (7) | 0.0023 (13) |
C8 | 0.0235 (10) | 0.020 (3) | 0.0165 (9) | −0.0015 (10) | 0.0073 (7) | −0.0055 (11) |
C9 | 0.0216 (11) | 0.027 (3) | 0.0176 (9) | 0.0062 (9) | 0.0071 (7) | 0.0035 (11) |
C10 | 0.0251 (11) | 0.019 (3) | 0.0187 (10) | 0.0044 (10) | 0.0079 (8) | 0.0005 (12) |
C11 | 0.0215 (10) | 0.020 (3) | 0.0251 (10) | 0.0030 (11) | 0.0068 (8) | 0.0035 (12) |
C12 | 0.0230 (11) | 0.037 (3) | 0.0253 (10) | 0.0010 (11) | 0.0142 (8) | 0.0058 (13) |
C13 | 0.0253 (11) | 0.029 (3) | 0.0183 (10) | 0.0066 (10) | 0.0095 (8) | 0.0025 (12) |
C14 | 0.0181 (11) | 0.030 (3) | 0.0185 (9) | 0.0077 (10) | 0.0060 (8) | 0.0040 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.221 (2) | C7—C8 | 1.491 (3) |
C1—C2 | 1.469 (2) | C8—C8i | 1.355 (4) |
C1—C14 | 1.463 (3) | C8—C9 | 1.499 (3) |
C2—C3 | 1.393 (3) | C9—C10 | 1.388 (3) |
C2—C7 | 1.398 (3) | C9—C14 | 1.404 (2) |
C3—C4 | 1.363 (3) | C10—C11 | 1.367 (3) |
C3—H1 | 0.950 | C10—H5 | 0.950 |
C4—C5 | 1.381 (3) | C11—C12 | 1.386 (3) |
C4—H2 | 0.950 | C11—H6 | 0.950 |
C5—C6 | 1.376 (3) | C12—C13 | 1.360 (3) |
C5—H3 | 0.950 | C12—H7 | 0.950 |
C6—C7 | 1.386 (3) | C13—C14 | 1.393 (3) |
C6—H4 | 0.950 | C13—H8 | 0.950 |
| | | |
O1—C1—C2 | 122.85 (17) | C7—C8—C8i | 124.3 (2) |
O1—C1—C14 | 121.86 (15) | C7—C8—C9 | 111.76 (16) |
C2—C1—C14 | 114.69 (17) | C8i—C8—C9 | 123.9 (2) |
C1—C2—C3 | 118.57 (16) | C8—C9—C10 | 123.92 (15) |
C1—C2—C7 | 120.22 (15) | C8—C9—C14 | 118.15 (17) |
C3—C2—C7 | 120.82 (15) | C10—C9—C14 | 117.93 (16) |
C2—C3—C4 | 120.25 (17) | C9—C10—C11 | 120.91 (16) |
C2—C3—H1 | 119.9 | C9—C10—H5 | 119.5 |
C4—C3—H1 | 119.9 | C11—C10—H5 | 119.6 |
C3—C4—C5 | 119.31 (16) | C10—C11—C12 | 120.53 (18) |
C3—C4—H2 | 120.3 | C10—C11—H6 | 119.7 |
C5—C4—H2 | 120.3 | C12—C11—H6 | 119.8 |
C4—C5—C6 | 121.11 (17) | C11—C12—C13 | 120.11 (17) |
C4—C5—H3 | 119.4 | C11—C12—H7 | 119.9 |
C6—C5—H3 | 119.5 | C13—C12—H7 | 120.0 |
C5—C6—C7 | 120.64 (17) | C12—C13—C14 | 119.82 (16) |
C5—C6—H4 | 119.7 | C12—C13—H8 | 120.1 |
C7—C6—H4 | 119.7 | C14—C13—H8 | 120.1 |
C2—C7—C6 | 117.80 (15) | C1—C14—C9 | 120.31 (15) |
C2—C7—C8 | 118.12 (15) | C1—C14—C13 | 118.99 (15) |
C6—C7—C8 | 124.07 (16) | C9—C14—C13 | 120.61 (17) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C28H16O2 | F(000) = 400 |
Mr = 384.43 | Dx = 1.716 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
Hall symbol: -P 2yn | Cell parameters from 1137 reflections |
a = 9.7527 (9) Å | θ = 3–15° |
b = 7.2058 (15) Å | µ = 0.11 mm−1 |
c = 11.2786 (9) Å | T = 293 K |
β = 110.132 (6)° | Block, yellow |
V = 744.19 (18) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Serial diffractometer | 506 reflections with I > 2.0σ(I) |
Silicon monochromator | Rint = 0.092 |
ω scans | θmax = 15.3°, θmin = 2.3° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −10→10 |
Tmin = 0.79, Tmax = 0.99 | k = 0→5 |
3280 measured reflections | l = 0→12 |
649 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.047 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
10.6 -8.46 6.32 |
S = 1.08 | (Δ/σ)max = 0.000251 |
506 reflections | Δρmax = 0.12 e Å−3 |
136 parameters | Δρmin = −0.12 e Å−3 |
187 restraints | |
Crystal data top
C28H16O2 | V = 744.19 (18) Å3 |
Mr = 384.43 | Z = 2 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
a = 9.7527 (9) Å | µ = 0.11 mm−1 |
b = 7.2058 (15) Å | T = 293 K |
c = 11.2786 (9) Å | 0.20 × 0.20 × 0.10 mm |
β = 110.132 (6)° | |
Data collection top
Serial diffractometer | 649 independent reflections |
Absorption correction: multi-scan SADABS (Siemens, 1996) | 506 reflections with I > 2.0σ(I) |
Tmin = 0.79, Tmax = 0.99 | Rint = 0.092 |
3280 measured reflections | θmax = 15.3° |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 187 restraints |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.12 e Å−3 |
506 reflections | Δρmin = −0.12 e Å−3 |
136 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.85647 (17) | 0.4514 (4) | 0.06684 (15) | 0.0293 | |
C1 | 0.8826 (2) | 0.5111 (5) | 0.17371 (19) | 0.0241 | |
C2 | 0.7722 (2) | 0.5192 (6) | 0.23469 (19) | 0.0199 | |
C3 | 0.6260 (2) | 0.5195 (6) | 0.1592 (2) | 0.0239 | |
C4 | 0.5206 (2) | 0.5550 (6) | 0.2102 (2) | 0.0294 | |
C5 | 0.5608 (2) | 0.5840 (6) | 0.3380 (2) | 0.0276 | |
C6 | 0.7052 (2) | 0.5845 (5) | 0.4148 (2) | 0.0240 | |
C7 | 0.8144 (2) | 0.5476 (5) | 0.36490 (19) | 0.0196 | |
C8 | 0.9730 (2) | 0.5397 (5) | 0.44193 (17) | 0.0160 | |
C9 | 1.0653 (2) | 0.6237 (5) | 0.37399 (18) | 0.0184 | |
C10 | 1.1918 (2) | 0.7221 (6) | 0.43362 (19) | 0.0225 | |
C11 | 1.2728 (2) | 0.7938 (6) | 0.3658 (2) | 0.0237 | |
C12 | 1.2269 (2) | 0.7734 (6) | 0.2367 (2) | 0.0250 | |
C13 | 1.1005 (2) | 0.6828 (5) | 0.17481 (19) | 0.0215 | |
C14 | 1.0199 (2) | 0.6045 (5) | 0.24237 (18) | 0.0207 | |
H1 | 0.5991 | 0.4940 | 0.0714 | 0.0275* | |
H2 | 0.4207 | 0.5604 | 0.1579 | 0.0357* | |
H3 | 0.4873 | 0.6038 | 0.3741 | 0.0351* | |
H4 | 0.7304 | 0.6101 | 0.5024 | 0.0274* | |
H5 | 1.2232 | 0.7405 | 0.5224 | 0.0275* | |
H6 | 1.3612 | 0.8578 | 0.4085 | 0.0282* | |
H7 | 1.2839 | 0.8230 | 0.1908 | 0.0313* | |
H8 | 1.0671 | 0.6730 | 0.0854 | 0.0273* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0360 (10) | 0.034 (3) | 0.0172 (9) | −0.0025 (10) | 0.0078 (7) | −0.0042 (10) |
C1 | 0.0281 (12) | 0.029 (4) | 0.0146 (11) | 0.0018 (12) | 0.0063 (9) | 0.0027 (13) |
C2 | 0.0242 (11) | 0.013 (4) | 0.0209 (11) | −0.0026 (13) | 0.0063 (8) | 0.0001 (14) |
C3 | 0.0275 (11) | 0.018 (4) | 0.0224 (13) | −0.0045 (14) | 0.0035 (9) | 0.0034 (15) |
C4 | 0.0217 (12) | 0.024 (4) | 0.0383 (12) | −0.0053 (14) | 0.0051 (9) | 0.0001 (18) |
C5 | 0.0259 (12) | 0.020 (4) | 0.0400 (12) | −0.0032 (14) | 0.0147 (10) | −0.0030 (18) |
C6 | 0.0291 (11) | 0.022 (4) | 0.0224 (13) | 0.0049 (14) | 0.0109 (8) | 0.0042 (16) |
C7 | 0.0233 (11) | 0.014 (4) | 0.0213 (11) | 0.0002 (13) | 0.0078 (8) | 0.0026 (15) |
C8 | 0.0243 (11) | 0.007 (4) | 0.0168 (10) | 0.0019 (12) | 0.0079 (8) | −0.0038 (13) |
C9 | 0.0219 (12) | 0.016 (4) | 0.0175 (10) | 0.0076 (10) | 0.0072 (8) | 0.0019 (13) |
C10 | 0.0220 (12) | 0.025 (4) | 0.0197 (12) | 0.0049 (12) | 0.0056 (9) | 0.0026 (14) |
C11 | 0.0216 (12) | 0.023 (4) | 0.0254 (11) | 0.0033 (12) | 0.0069 (9) | 0.0022 (15) |
C12 | 0.0226 (13) | 0.031 (4) | 0.0253 (11) | 0.0025 (12) | 0.0132 (9) | 0.0056 (16) |
C13 | 0.0247 (12) | 0.024 (4) | 0.0182 (11) | 0.0061 (12) | 0.0110 (9) | 0.0004 (14) |
C14 | 0.0192 (12) | 0.026 (4) | 0.0167 (10) | 0.0071 (11) | 0.0066 (9) | 0.0039 (14) |
Geometric parameters (Å, º) top
O1—C1 | 1.221 (3) | C7—C8 | 1.492 (3) |
C1—C2 | 1.465 (3) | C8—C8i | 1.359 (4) |
C1—C14 | 1.460 (3) | C8—C9 | 1.496 (3) |
C2—C3 | 1.386 (3) | C9—C10 | 1.381 (4) |
C2—C7 | 1.397 (3) | C9—C14 | 1.402 (3) |
C3—C4 | 1.364 (3) | C10—C11 | 1.375 (3) |
C3—H1 | 0.950 | C10—H5 | 0.950 |
C4—C5 | 1.373 (3) | C11—C12 | 1.376 (3) |
C4—H2 | 0.950 | C11—H6 | 0.950 |
C5—C6 | 1.376 (3) | C12—C13 | 1.357 (4) |
C5—H3 | 0.950 | C12—H7 | 0.950 |
C6—C7 | 1.391 (3) | C13—C14 | 1.389 (3) |
C6—H4 | 0.950 | C13—H8 | 0.950 |
| | | |
O1—C1—C2 | 122.68 (18) | C7—C8—C8i | 123.9 (3) |
O1—C1—C14 | 121.85 (17) | C7—C8—C9 | 111.88 (17) |
C2—C1—C14 | 114.88 (18) | C8i—C8—C9 | 124.2 (2) |
C1—C2—C3 | 118.56 (17) | C8—C9—C10 | 123.54 (16) |
C1—C2—C7 | 120.07 (16) | C8—C9—C14 | 118.42 (18) |
C3—C2—C7 | 120.96 (16) | C10—C9—C14 | 118.03 (17) |
C2—C3—C4 | 120.39 (19) | C9—C10—C11 | 120.65 (17) |
C2—C3—H1 | 119.8 | C9—C10—H5 | 119.7 |
C4—C3—H1 | 119.8 | C11—C10—H5 | 119.7 |
C3—C4—C5 | 119.13 (18) | C10—C11—C12 | 120.6 (2) |
C3—C4—H2 | 120.4 | C10—C11—H6 | 119.7 |
C5—C4—H2 | 120.5 | C12—C11—H6 | 119.7 |
C4—C5—C6 | 121.47 (18) | C11—C12—C13 | 120.16 (19) |
C4—C5—H3 | 119.3 | C11—C12—H7 | 119.9 |
C6—C5—H3 | 119.3 | C13—C12—H7 | 119.9 |
C5—C6—C7 | 120.30 (18) | C12—C13—C14 | 119.92 (17) |
C5—C6—H4 | 119.9 | C12—C13—H8 | 120.0 |
C7—C6—H4 | 119.8 | C14—C13—H8 | 120.0 |
C2—C7—C6 | 117.64 (16) | C1—C14—C9 | 120.31 (16) |
C2—C7—C8 | 118.55 (16) | C1—C14—C13 | 119.03 (16) |
C6—C7—C8 | 123.80 (17) | C9—C14—C13 | 120.58 (18) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C28H16O2 | F(000) = 400 |
Mr = 384.43 | Dx = 1.748 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
Hall symbol: -P 2yn | Cell parameters from 975 reflections |
a = 9.7286 (10) Å | θ = 3–15° |
b = 7.1123 (17) Å | µ = 0.11 mm−1 |
c = 11.2468 (11) Å | T = 293 K |
β = 110.186 (7)° | Block, yellow |
V = 730.4 (2) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Serial diffractometer | 487 reflections with I > 2.0σ(I) |
Silicon monochromator | Rint = 0.081 |
ω scans | θmax = 15.4°, θmin = 2.3° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −10→10 |
Tmin = 0.76, Tmax = 0.99 | k = 0→5 |
3365 measured reflections | l = 0→12 |
623 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.029 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
8.57 -9.18 3.12 -0.995E-01 |
S = 1.10 | (Δ/σ)max = 0.000312 |
487 reflections | Δρmax = 0.14 e Å−3 |
136 parameters | Δρmin = −0.15 e Å−3 |
187 restraints | |
Crystal data top
C28H16O2 | V = 730.4 (2) Å3 |
Mr = 384.43 | Z = 2 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
a = 9.7286 (10) Å | µ = 0.11 mm−1 |
b = 7.1123 (17) Å | T = 293 K |
c = 11.2468 (11) Å | 0.20 × 0.20 × 0.10 mm |
β = 110.186 (7)° | |
Data collection top
Serial diffractometer | 623 independent reflections |
Absorption correction: multi-scan SADABS (Siemens, 1996) | 487 reflections with I > 2.0σ(I) |
Tmin = 0.76, Tmax = 0.99 | Rint = 0.081 |
3365 measured reflections | θmax = 15.4° |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 187 restraints |
wR(F2) = 0.029 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.14 e Å−3 |
487 reflections | Δρmin = −0.15 e Å−3 |
136 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.85496 (15) | 0.4511 (4) | 0.06535 (14) | 0.0317 | |
C1 | 0.88153 (19) | 0.5112 (5) | 0.17278 (18) | 0.0219 | |
C2 | 0.77098 (19) | 0.5190 (5) | 0.23328 (17) | 0.0195 | |
C3 | 0.6245 (2) | 0.5222 (6) | 0.15741 (19) | 0.0286 | |
C4 | 0.5191 (2) | 0.5567 (6) | 0.2086 (2) | 0.0309 | |
C5 | 0.5596 (2) | 0.5849 (6) | 0.3372 (2) | 0.0335 | |
C6 | 0.7040 (2) | 0.5832 (6) | 0.41397 (19) | 0.0282 | |
C7 | 0.8136 (2) | 0.5473 (5) | 0.36421 (18) | 0.0221 | |
C8 | 0.9727 (2) | 0.5388 (5) | 0.44127 (17) | 0.0202 | |
C9 | 1.0650 (2) | 0.6232 (5) | 0.37349 (18) | 0.0226 | |
C10 | 1.1927 (2) | 0.7238 (5) | 0.43250 (19) | 0.0254 | |
C11 | 1.2739 (2) | 0.7944 (5) | 0.36493 (19) | 0.0252 | |
C12 | 1.2263 (2) | 0.7768 (5) | 0.23462 (19) | 0.0284 | |
C13 | 1.0991 (2) | 0.6855 (6) | 0.17332 (18) | 0.0258 | |
C14 | 1.0188 (2) | 0.6046 (5) | 0.24091 (17) | 0.0225 | |
H1 | 0.5975 | 0.5000 | 0.0690 | 0.0335* | |
H2 | 0.4188 | 0.5611 | 0.1563 | 0.0353* | |
H3 | 0.4860 | 0.6061 | 0.3735 | 0.0418* | |
H4 | 0.7292 | 0.6067 | 0.5021 | 0.0345* | |
H5 | 1.2242 | 0.7439 | 0.5214 | 0.0305* | |
H6 | 1.3639 | 0.8563 | 0.4080 | 0.0307* | |
H7 | 1.2824 | 0.8283 | 0.1882 | 0.0362* | |
H8 | 1.0647 | 0.6768 | 0.0835 | 0.0324* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0347 (9) | 0.041 (3) | 0.0196 (8) | −0.0018 (10) | 0.0091 (6) | −0.0045 (10) |
C1 | 0.0295 (11) | 0.019 (4) | 0.0164 (10) | 0.0038 (12) | 0.0065 (8) | 0.0044 (13) |
C2 | 0.0255 (10) | 0.009 (4) | 0.0218 (10) | −0.0028 (12) | 0.0059 (7) | 0.0034 (14) |
C3 | 0.0276 (10) | 0.030 (5) | 0.0240 (12) | −0.0057 (14) | 0.0039 (8) | 0.0051 (15) |
C4 | 0.0225 (11) | 0.027 (4) | 0.0396 (11) | −0.0046 (14) | 0.0056 (9) | −0.0001 (17) |
C5 | 0.0251 (10) | 0.039 (4) | 0.0405 (12) | −0.0006 (15) | 0.0165 (9) | 0.0030 (18) |
C6 | 0.0284 (10) | 0.034 (4) | 0.0239 (12) | 0.0017 (14) | 0.0114 (8) | 0.0017 (15) |
C7 | 0.0221 (10) | 0.023 (4) | 0.0220 (9) | 0.0004 (13) | 0.0080 (8) | 0.0033 (14) |
C8 | 0.0249 (10) | 0.019 (4) | 0.0172 (9) | 0.0031 (13) | 0.0079 (8) | −0.0038 (13) |
C9 | 0.0194 (11) | 0.030 (4) | 0.0189 (9) | 0.0083 (11) | 0.0072 (8) | 0.0015 (12) |
C10 | 0.0233 (11) | 0.032 (4) | 0.0197 (10) | 0.0048 (12) | 0.0063 (8) | 0.0002 (13) |
C11 | 0.0211 (11) | 0.027 (4) | 0.0265 (10) | 0.0037 (12) | 0.0070 (8) | 0.0014 (15) |
C12 | 0.0221 (12) | 0.041 (4) | 0.0243 (10) | 0.0034 (12) | 0.0110 (9) | 0.0062 (15) |
C13 | 0.0257 (11) | 0.037 (4) | 0.0173 (10) | 0.0046 (12) | 0.0111 (8) | 0.0006 (13) |
C14 | 0.0218 (11) | 0.026 (4) | 0.0195 (10) | 0.0075 (11) | 0.0068 (8) | 0.0045 (13) |
Geometric parameters (Å, º) top
O1—C1 | 1.222 (3) | C7—C8 | 1.491 (3) |
C1—C2 | 1.459 (2) | C8—C8i | 1.359 (4) |
C1—C14 | 1.451 (3) | C8—C9 | 1.490 (3) |
C2—C3 | 1.385 (3) | C9—C10 | 1.388 (3) |
C2—C7 | 1.400 (3) | C9—C14 | 1.407 (3) |
C3—C4 | 1.361 (3) | C10—C11 | 1.367 (3) |
C3—H1 | 0.950 | C10—H5 | 0.950 |
C4—C5 | 1.377 (3) | C11—C12 | 1.382 (3) |
C4—H2 | 0.950 | C11—H6 | 0.950 |
C5—C6 | 1.372 (3) | C12—C13 | 1.356 (3) |
C5—H3 | 0.950 | C12—H7 | 0.950 |
C6—C7 | 1.389 (3) | C13—C14 | 1.389 (3) |
C6—H4 | 0.950 | C13—H8 | 0.950 |
| | | |
O1—C1—C2 | 122.40 (17) | C7—C8—C8i | 124.1 (3) |
O1—C1—C14 | 121.63 (16) | C7—C8—C9 | 111.96 (17) |
C2—C1—C14 | 115.37 (17) | C8i—C8—C9 | 124.0 (2) |
C1—C2—C3 | 118.71 (16) | C8—C9—C10 | 124.12 (16) |
C1—C2—C7 | 119.84 (15) | C8—C9—C14 | 118.39 (17) |
C3—C2—C7 | 120.94 (16) | C10—C9—C14 | 117.47 (17) |
C2—C3—C4 | 120.50 (18) | C9—C10—C11 | 121.14 (17) |
C2—C3—H1 | 119.7 | C9—C10—H5 | 119.4 |
C4—C3—H1 | 119.8 | C11—C10—H5 | 119.4 |
C3—C4—C5 | 119.12 (17) | C10—C11—C12 | 120.66 (19) |
C3—C4—H2 | 120.4 | C10—C11—H6 | 119.7 |
C5—C4—H2 | 120.4 | C12—C11—H6 | 119.7 |
C4—C5—C6 | 121.29 (17) | C11—C12—C13 | 119.72 (19) |
C4—C5—H3 | 119.3 | C11—C12—H7 | 120.2 |
C6—C5—H3 | 119.4 | C13—C12—H7 | 120.1 |
C5—C6—C7 | 120.70 (18) | C12—C13—C14 | 120.46 (16) |
C5—C6—H4 | 119.6 | C12—C13—H8 | 119.8 |
C7—C6—H4 | 119.7 | C14—C13—H8 | 119.8 |
C2—C7—C6 | 117.40 (15) | C1—C14—C9 | 120.14 (16) |
C2—C7—C8 | 118.48 (15) | C1—C14—C13 | 119.31 (15) |
C6—C7—C8 | 124.11 (17) | C9—C14—C13 | 120.42 (18) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C28H16O2 | F(000) = 400 |
Mr = 384.43 | Dx = 1.772 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
Hall symbol: -P 2yn | Cell parameters from 875 reflections |
a = 9.7119 (14) Å | θ = 2–15° |
b = 7.041 (2) Å | µ = 0.11 mm−1 |
c = 11.2282 (18) Å | T = 293 K |
β = 110.229 (10)° | Block, yellow |
V = 720.4 (3) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Area diffractometer | 473 reflections with I > 2.0σ(I) |
Silicon monochromator | Rint = 0.117 |
ω scans | θmax = 15.1°, θmin = 2.3° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −10→9 |
Tmin = 0.81, Tmax = 0.99 | k = 0→5 |
3016 measured reflections | l = 0→12 |
641 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.039 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
9.17 -8.98 2.74 |
S = 1.09 | (Δ/σ)max = 0.000185 |
473 reflections | Δρmax = 0.19 e Å−3 |
136 parameters | Δρmin = −0.19 e Å−3 |
187 restraints | |
Crystal data top
C28H16O2 | V = 720.4 (3) Å3 |
Mr = 384.43 | Z = 2 |
Monoclinic, P21/n | Synchrotron radiation, λ = 0.47920 Å |
a = 9.7119 (14) Å | µ = 0.11 mm−1 |
b = 7.041 (2) Å | T = 293 K |
c = 11.2282 (18) Å | 0.20 × 0.20 × 0.10 mm |
β = 110.229 (10)° | |
Data collection top
Area diffractometer | 641 independent reflections |
Absorption correction: multi-scan SADABS (Siemens, 1996) | 473 reflections with I > 2.0σ(I) |
Tmin = 0.81, Tmax = 0.99 | Rint = 0.117 |
3016 measured reflections | θmax = 15.1° |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 187 restraints |
wR(F2) = 0.039 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.19 e Å−3 |
473 reflections | Δρmin = −0.19 e Å−3 |
136 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.8538 (2) | 0.4519 (5) | 0.0636 (2) | 0.0290 | |
C1 | 0.8808 (3) | 0.5094 (7) | 0.1719 (2) | 0.0195 | |
C2 | 0.7698 (3) | 0.5180 (7) | 0.2325 (2) | 0.0212 | |
C3 | 0.6232 (3) | 0.5236 (7) | 0.1561 (3) | 0.0232 | |
C4 | 0.5177 (3) | 0.5585 (8) | 0.2073 (3) | 0.0286 | |
C5 | 0.5579 (3) | 0.5850 (8) | 0.3361 (3) | 0.0291 | |
C6 | 0.7034 (3) | 0.5831 (7) | 0.4136 (3) | 0.0233 | |
C7 | 0.8123 (3) | 0.5467 (7) | 0.3632 (2) | 0.0191 | |
C8 | 0.9720 (3) | 0.5374 (6) | 0.4407 (2) | 0.0194 | |
C9 | 1.0649 (3) | 0.6239 (6) | 0.3723 (2) | 0.0228 | |
C10 | 1.1927 (3) | 0.7222 (7) | 0.4321 (2) | 0.0273 | |
C11 | 1.2740 (3) | 0.7962 (7) | 0.3641 (3) | 0.0263 | |
C12 | 1.2262 (3) | 0.7785 (7) | 0.2338 (3) | 0.0248 | |
C13 | 1.0977 (3) | 0.6867 (7) | 0.1720 (2) | 0.0238 | |
C14 | 1.0180 (3) | 0.6056 (6) | 0.2403 (2) | 0.0211 | |
H1 | 0.5962 | 0.5029 | 0.0673 | 0.0263* | |
H2 | 0.4174 | 0.5639 | 0.1546 | 0.0327* | |
H3 | 0.4841 | 0.6055 | 0.3724 | 0.0369* | |
H4 | 0.7291 | 0.6072 | 0.5019 | 0.0278* | |
H5 | 1.2252 | 0.7396 | 0.5215 | 0.0325* | |
H6 | 1.3638 | 0.8598 | 0.4071 | 0.0294* | |
H7 | 1.2824 | 0.8305 | 0.1872 | 0.0317* | |
H8 | 1.0630 | 0.6776 | 0.0820 | 0.0299* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0409 (14) | 0.024 (4) | 0.0208 (12) | −0.0029 (15) | 0.0089 (10) | −0.0025 (12) |
C1 | 0.0320 (16) | 0.006 (4) | 0.0194 (14) | 0.0056 (17) | 0.0072 (12) | 0.0041 (15) |
C2 | 0.0287 (13) | 0.012 (4) | 0.0216 (13) | −0.006 (2) | 0.0069 (10) | 0.0027 (17) |
C3 | 0.0301 (14) | 0.008 (5) | 0.0267 (17) | −0.006 (2) | 0.0038 (11) | 0.0031 (16) |
C4 | 0.0268 (17) | 0.015 (5) | 0.0405 (16) | −0.006 (2) | 0.0068 (14) | 0.001 (2) |
C5 | 0.0305 (15) | 0.017 (5) | 0.0429 (17) | 0.001 (2) | 0.0165 (13) | −0.002 (2) |
C6 | 0.0345 (14) | 0.008 (5) | 0.0300 (19) | 0.002 (2) | 0.0144 (11) | 0.0015 (18) |
C7 | 0.0274 (13) | 0.008 (4) | 0.0220 (13) | −0.002 (2) | 0.0083 (10) | 0.0030 (16) |
C8 | 0.0278 (13) | 0.014 (4) | 0.0174 (14) | −0.003 (2) | 0.0094 (11) | −0.0080 (16) |
C9 | 0.0192 (16) | 0.031 (5) | 0.0183 (13) | 0.0066 (17) | 0.0071 (11) | 0.0028 (15) |
C10 | 0.0248 (17) | 0.039 (5) | 0.0161 (15) | 0.0018 (18) | 0.0053 (12) | 0.0018 (16) |
C11 | 0.0237 (17) | 0.028 (5) | 0.0261 (14) | 0.001 (2) | 0.0075 (12) | 0.0032 (18) |
C12 | 0.0282 (18) | 0.025 (5) | 0.0246 (14) | 0.0045 (19) | 0.0135 (13) | 0.0019 (17) |
C13 | 0.0274 (17) | 0.026 (4) | 0.0192 (16) | 0.0064 (17) | 0.0099 (12) | 0.0005 (15) |
C14 | 0.0256 (16) | 0.019 (5) | 0.0188 (13) | 0.0070 (17) | 0.0074 (11) | 0.0021 (15) |
Geometric parameters (Å, º) top
O1—C1 | 1.221 (3) | C7—C8 | 1.495 (4) |
C1—C2 | 1.461 (3) | C8—C8i | 1.358 (5) |
C1—C14 | 1.454 (4) | C8—C9 | 1.501 (4) |
C2—C3 | 1.385 (4) | C9—C10 | 1.377 (4) |
C2—C7 | 1.396 (3) | C9—C14 | 1.397 (3) |
C3—C4 | 1.359 (4) | C10—C11 | 1.377 (4) |
C3—H1 | 0.950 | C10—H5 | 0.950 |
C4—C5 | 1.374 (4) | C11—C12 | 1.379 (4) |
C4—H2 | 0.950 | C11—H6 | 0.950 |
C5—C6 | 1.380 (4) | C12—C13 | 1.363 (4) |
C5—H3 | 0.950 | C12—H7 | 0.950 |
C6—C7 | 1.385 (4) | C13—C14 | 1.388 (4) |
C6—H4 | 0.950 | C13—H8 | 0.950 |
| | | |
O1—C1—C2 | 122.6 (2) | C7—C8—C8i | 124.8 (3) |
O1—C1—C14 | 121.5 (2) | C7—C8—C9 | 111.7 (2) |
C2—C1—C14 | 115.1 (2) | C8i—C8—C9 | 123.5 (3) |
C1—C2—C3 | 118.6 (2) | C8—C9—C10 | 123.6 (2) |
C1—C2—C7 | 119.88 (19) | C8—C9—C14 | 118.2 (2) |
C3—C2—C7 | 120.91 (19) | C10—C9—C14 | 118.2 (2) |
C2—C3—C4 | 120.5 (2) | C9—C10—C11 | 120.9 (2) |
C2—C3—H1 | 119.8 | C9—C10—H5 | 119.6 |
C4—C3—H1 | 119.7 | C11—C10—H5 | 119.5 |
C3—C4—C5 | 119.2 (2) | C10—C11—C12 | 120.5 (2) |
C3—C4—H2 | 120.3 | C10—C11—H6 | 119.8 |
C5—C4—H2 | 120.4 | C12—C11—H6 | 119.7 |
C4—C5—C6 | 121.2 (2) | C11—C12—C13 | 119.8 (2) |
C4—C5—H3 | 119.4 | C11—C12—H7 | 120.2 |
C6—C5—H3 | 119.4 | C13—C12—H7 | 120.1 |
C5—C6—C7 | 120.3 (2) | C12—C13—C14 | 120.1 (2) |
C5—C6—H4 | 119.9 | C12—C13—H8 | 120.0 |
C7—C6—H4 | 119.8 | C14—C13—H8 | 120.0 |
C2—C7—C6 | 117.8 (2) | C1—C14—C9 | 120.40 (19) |
C2—C7—C8 | 118.42 (19) | C1—C14—C13 | 119.0 (2) |
C6—C7—C8 | 123.8 (2) | C9—C14—C13 | 120.6 (2) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Experimental details
| (ambient) | (1.2GPa) | (2.2GPa) | (3.3GPa) |
Crystal data |
Chemical formula | C28H16O2 | C28H16O2 | C28H16O2 | C28H16O2 |
Mr | 384.43 | 384.43 | 384.43 | 384.43 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 10.1860 (3), 8.4277 (2), 11.6457 (3) | 9.9825 (11), 7.8892 (15), 11.4879 (9) | 9.9021 (14), 7.6543 (18), 11.4225 (11) | 9.8354 (13), 7.4567 (19), 11.3543 (12) |
β (°) | 109.591 (2) | 109.780 (6) | 109.860 (9) | 109.939 (8) |
V (Å3) | 941.85 (4) | 851.3 (2) | 814.3 (2) | 782.8 (2) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Synchrotron, λ = 0.47920 Å | Synchrotron, λ = 0.47920 Å | Synchrotron, λ = 0.47920 Å |
µ (mm−1) | 0.08 | 0.09 | 0.10 | 0.10 |
Crystal size (mm) | 0.57 × 0.33 × 0.31 | 0.20 × 0.20 × 0.10 | 0.20 × 0.20 × 0.10 | 0.20 × 0.20 × 0.10 |
|
Data collection |
Diffractometer | Area diffractometer | Serial diffractometer | Serial diffractometer | Serial diffractometer |
Absorption correction | Multi-scan SADABS (Siemens, 1996) | Multi-scan SADABS (Siemens, 1996) | Multi-scan SADABS (Siemens, 1996) | Multi-scan SADABS (Siemens, 1996) |
Tmin, Tmax | 0.82, 0.97 | 0.86, 0.99 | 0.78, 0.99 | 0.84, 0.99 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 12386, 2349, 1867 | 4044, 852, 644 | 3792, 818, 625 | 3798, 772, 583 |
Rint | 0.049 | 0.087 | 0.087 | 0.093 |
θmax (°) | 28.3 | 15.4 | 15.5 | 15.5 |
(sin θ/λ)max (Å−1) | 0.667 | 0.555 | 0.558 | 0.556 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.051, 1.11 | 0.045, 0.044, 1.01 | 0.044, 0.047, 1.04 | 0.042, 0.043, 1.04 |
No. of reflections | 1867 | 644 | 625 | 583 |
No. of parameters | 136 | 136 | 136 | 136 |
No. of restraints | 0 | 187 | 187 | 187 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.19 | 0.12, −0.13 | 0.15, −0.15 | 0.15, −0.16 |
| (4.2GPa) | (5.1GPa) | (6.0GPa) | (6.5GPa) |
Crystal data |
Chemical formula | C28H16O2 | C28H16O2 | C28H16O2 | C28H16O2 |
Mr | 384.43 | 384.43 | 384.43 | 384.43 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 9.7854 (7), 7.2988 (11), 11.3074 (7) | 9.7527 (9), 7.2058 (15), 11.2786 (9) | 9.7286 (10), 7.1123 (17), 11.2468 (11) | 9.7119 (14), 7.041 (2), 11.2282 (18) |
β (°) | 110.028 (4) | 110.132 (6) | 110.186 (7) | 110.229 (10) |
V (Å3) | 758.75 (14) | 744.19 (18) | 730.4 (2) | 720.4 (3) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Synchrotron, λ = 0.47920 Å | Synchrotron, λ = 0.47920 Å | Synchrotron, λ = 0.47920 Å | Synchrotron, λ = 0.47920 Å |
µ (mm−1) | 0.11 | 0.11 | 0.11 | 0.11 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 | 0.20 × 0.20 × 0.10 | 0.20 × 0.20 × 0.10 | 0.20 × 0.20 × 0.10 |
|
Data collection |
Diffractometer | Serial diffractometer | Serial diffractometer | Serial diffractometer | Area diffractometer |
Absorption correction | Multi-scan SADABS (Siemens, 1996) | Multi-scan SADABS (Siemens, 1996) | Multi-scan SADABS (Siemens, 1996) | Multi-scan SADABS (Siemens, 1996) |
Tmin, Tmax | 0.84, 0.99 | 0.79, 0.99 | 0.76, 0.99 | 0.81, 0.99 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 3269, 689, 554 | 3280, 649, 506 | 3365, 623, 487 | 3016, 641, 473 |
Rint | 0.074 | 0.092 | 0.081 | 0.117 |
θmax (°) | 15.4 | 15.3 | 15.4 | 15.1 |
(sin θ/λ)max (Å−1) | 0.556 | 0.550 | 0.556 | 0.544 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.044, 1.07 | 0.041, 0.047, 1.08 | 0.041, 0.029, 1.10 | 0.051, 0.039, 1.09 |
No. of reflections | 554 | 506 | 487 | 473 |
No. of parameters | 136 | 136 | 136 | 136 |
No. of restraints | 187 | 187 | 187 | 187 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.16 | 0.12, −0.12 | 0.14, −0.15 | 0.19, −0.19 |
Selected geometric parameters (Å, º) for (ambient) topO1—C1 | 1.2193 (17) | C7—C8 | 1.490 (2) |
C1—C2 | 1.481 (2) | C8—C8i | 1.357 (3) |
C1—C14 | 1.484 (2) | C8—C9 | 1.4907 (19) |
C2—C3 | 1.391 (2) | C9—C10 | 1.392 (2) |
C2—C7 | 1.4004 (19) | C9—C14 | 1.4066 (19) |
C3—C4 | 1.373 (3) | C10—C11 | 1.379 (2) |
C4—C5 | 1.380 (3) | C11—C12 | 1.382 (2) |
C5—C6 | 1.376 (2) | C12—C13 | 1.370 (2) |
C6—C7 | 1.393 (2) | C13—C14 | 1.395 (2) |
| | | |
O1—C1—C2 | 122.58 (15) | C7—C8—C8i | 123.56 (16) |
O1—C1—C14 | 121.83 (15) | C7—C8—C9 | 112.11 (11) |
C2—C1—C14 | 115.12 (12) | C8i—C8—C9 | 124.23 (16) |
C1—C2—C3 | 119.80 (14) | C8—C9—C10 | 123.89 (12) |
C1—C2—C7 | 119.75 (13) | C8—C9—C14 | 117.69 (13) |
C3—C2—C7 | 120.12 (15) | C10—C9—C14 | 118.41 (13) |
C2—C3—C4 | 120.30 (16) | C9—C10—C11 | 120.59 (14) |
C3—C4—C5 | 119.69 (16) | C10—C11—C12 | 120.49 (16) |
C4—C5—C6 | 120.76 (17) | C11—C12—C13 | 120.15 (15) |
C5—C6—C7 | 120.45 (16) | C12—C13—C14 | 120.12 (14) |
C2—C7—C6 | 118.42 (14) | C1—C14—C9 | 119.91 (13) |
C2—C7—C8 | 117.83 (13) | C1—C14—C13 | 119.77 (13) |
C6—C7—C8 | 123.74 (13) | C9—C14—C13 | 120.14 (14) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (1.2GPa) topO1—C1 | 1.223 (2) | C7—C8 | 1.493 (3) |
C1—C2 | 1.476 (3) | C8—C8i | 1.353 (4) |
C1—C14 | 1.474 (3) | C8—C9 | 1.497 (3) |
C2—C3 | 1.393 (3) | C9—C10 | 1.384 (3) |
C2—C7 | 1.400 (3) | C9—C14 | 1.406 (2) |
C3—C4 | 1.366 (3) | C10—C11 | 1.372 (3) |
C4—C5 | 1.378 (3) | C11—C12 | 1.380 (3) |
C5—C6 | 1.379 (3) | C12—C13 | 1.364 (3) |
C6—C7 | 1.391 (3) | C13—C14 | 1.394 (3) |
| | | |
O1—C1—C2 | 122.51 (17) | C7—C8—C8i | 123.8 (3) |
O1—C1—C14 | 121.69 (17) | C7—C8—C9 | 111.83 (16) |
C2—C1—C14 | 115.29 (16) | C8i—C8—C9 | 124.4 (2) |
C1—C2—C3 | 119.68 (16) | C8—C9—C10 | 124.15 (16) |
C1—C2—C7 | 119.81 (15) | C8—C9—C14 | 117.62 (17) |
C3—C2—C7 | 120.13 (17) | C10—C9—C14 | 118.23 (17) |
C2—C3—C4 | 120.47 (18) | C9—C10—C11 | 121.13 (17) |
C3—C4—C5 | 119.68 (18) | C10—C11—C12 | 120.19 (19) |
C4—C5—C6 | 120.78 (19) | C11—C12—C13 | 120.29 (18) |
C5—C6—C7 | 120.45 (18) | C12—C13—C14 | 120.09 (17) |
C2—C7—C6 | 118.29 (16) | C1—C14—C9 | 120.17 (15) |
C2—C7—C8 | 117.90 (16) | C1—C14—C13 | 119.62 (15) |
C6—C7—C8 | 123.80 (16) | C9—C14—C13 | 120.01 (17) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (2.2GPa) topO1—C1 | 1.225 (2) | C7—C8 | 1.494 (3) |
C1—C2 | 1.473 (3) | C8—C8i | 1.352 (4) |
C1—C14 | 1.466 (3) | C8—C9 | 1.496 (3) |
C2—C3 | 1.392 (3) | C9—C10 | 1.399 (3) |
C2—C7 | 1.401 (3) | C9—C14 | 1.408 (3) |
C3—C4 | 1.371 (3) | C10—C11 | 1.371 (3) |
C4—C5 | 1.376 (3) | C11—C12 | 1.383 (3) |
C5—C6 | 1.372 (3) | C12—C13 | 1.369 (3) |
C6—C7 | 1.392 (3) | C13—C14 | 1.392 (3) |
| | | |
O1—C1—C2 | 122.50 (17) | C7—C8—C8i | 124.2 (3) |
O1—C1—C14 | 121.78 (17) | C7—C8—C9 | 111.79 (17) |
C2—C1—C14 | 115.24 (17) | C8i—C8—C9 | 124.0 (2) |
C1—C2—C3 | 119.35 (16) | C8—C9—C10 | 123.91 (17) |
C1—C2—C7 | 119.97 (16) | C8—C9—C14 | 118.09 (17) |
C3—C2—C7 | 120.30 (16) | C10—C9—C14 | 117.96 (17) |
C2—C3—C4 | 120.16 (19) | C9—C10—C11 | 120.66 (18) |
C3—C4—C5 | 119.71 (19) | C10—C11—C12 | 120.74 (19) |
C4—C5—C6 | 120.98 (19) | C11—C12—C13 | 119.99 (19) |
C5—C6—C7 | 120.57 (18) | C12—C13—C14 | 120.16 (18) |
C2—C7—C6 | 118.16 (16) | C1—C14—C9 | 120.04 (16) |
C2—C7—C8 | 117.84 (16) | C1—C14—C13 | 119.49 (16) |
C6—C7—C8 | 124.00 (17) | C9—C14—C13 | 120.38 (17) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (3.3GPa) topO1—C1 | 1.220 (3) | C7—C8 | 1.493 (3) |
C1—C2 | 1.471 (3) | C8—C8i | 1.354 (4) |
C1—C14 | 1.469 (3) | C8—C9 | 1.497 (3) |
C2—C3 | 1.391 (3) | C9—C10 | 1.390 (3) |
C2—C7 | 1.399 (3) | C9—C14 | 1.407 (3) |
C3—C4 | 1.367 (3) | C10—C11 | 1.373 (3) |
C4—C5 | 1.374 (3) | C11—C12 | 1.376 (3) |
C5—C6 | 1.380 (3) | C12—C13 | 1.361 (4) |
C6—C7 | 1.380 (3) | C13—C14 | 1.392 (3) |
| | | |
O1—C1—C2 | 122.54 (18) | C7—C8—C8i | 124.1 (3) |
O1—C1—C14 | 121.84 (17) | C7—C8—C9 | 112.07 (17) |
C2—C1—C14 | 115.12 (17) | C8i—C8—C9 | 123.8 (2) |
C1—C2—C3 | 118.85 (17) | C8—C9—C10 | 124.05 (17) |
C1—C2—C7 | 120.21 (16) | C8—C9—C14 | 118.14 (18) |
C3—C2—C7 | 120.55 (16) | C10—C9—C14 | 117.80 (17) |
C2—C3—C4 | 120.36 (19) | C9—C10—C11 | 120.65 (18) |
C3—C4—C5 | 119.23 (19) | C10—C11—C12 | 120.9 (2) |
C4—C5—C6 | 121.16 (19) | C11—C12—C13 | 119.99 (19) |
C5—C6—C7 | 120.58 (19) | C12—C13—C14 | 120.05 (18) |
C2—C7—C6 | 118.01 (16) | C1—C14—C9 | 119.92 (16) |
C2—C7—C8 | 117.80 (16) | C1—C14—C13 | 119.46 (17) |
C6—C7—C8 | 124.19 (18) | C9—C14—C13 | 120.52 (18) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (4.2GPa) topO1—C1 | 1.221 (2) | C7—C8 | 1.491 (3) |
C1—C2 | 1.469 (2) | C8—C8i | 1.355 (4) |
C1—C14 | 1.463 (3) | C8—C9 | 1.499 (3) |
C2—C3 | 1.393 (3) | C9—C10 | 1.388 (3) |
C2—C7 | 1.398 (3) | C9—C14 | 1.404 (2) |
C3—C4 | 1.363 (3) | C10—C11 | 1.367 (3) |
C4—C5 | 1.381 (3) | C11—C12 | 1.386 (3) |
C5—C6 | 1.376 (3) | C12—C13 | 1.360 (3) |
C6—C7 | 1.386 (3) | C13—C14 | 1.393 (3) |
| | | |
O1—C1—C2 | 122.85 (17) | C7—C8—C8i | 124.3 (2) |
O1—C1—C14 | 121.86 (15) | C7—C8—C9 | 111.76 (16) |
C2—C1—C14 | 114.69 (17) | C8i—C8—C9 | 123.9 (2) |
C1—C2—C3 | 118.57 (16) | C8—C9—C10 | 123.92 (15) |
C1—C2—C7 | 120.22 (15) | C8—C9—C14 | 118.15 (17) |
C3—C2—C7 | 120.82 (15) | C10—C9—C14 | 117.93 (16) |
C2—C3—C4 | 120.25 (17) | C9—C10—C11 | 120.91 (16) |
C3—C4—C5 | 119.31 (16) | C10—C11—C12 | 120.53 (18) |
C4—C5—C6 | 121.11 (17) | C11—C12—C13 | 120.11 (17) |
C5—C6—C7 | 120.64 (17) | C12—C13—C14 | 119.82 (16) |
C2—C7—C6 | 117.80 (15) | C1—C14—C9 | 120.31 (15) |
C2—C7—C8 | 118.12 (15) | C1—C14—C13 | 118.99 (15) |
C6—C7—C8 | 124.07 (16) | C9—C14—C13 | 120.61 (17) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (5.1GPa) topO1—C1 | 1.221 (3) | C7—C8 | 1.492 (3) |
C1—C2 | 1.465 (3) | C8—C8i | 1.359 (4) |
C1—C14 | 1.460 (3) | C8—C9 | 1.496 (3) |
C2—C3 | 1.386 (3) | C9—C10 | 1.381 (4) |
C2—C7 | 1.397 (3) | C9—C14 | 1.402 (3) |
C3—C4 | 1.364 (3) | C10—C11 | 1.375 (3) |
C4—C5 | 1.373 (3) | C11—C12 | 1.376 (3) |
C5—C6 | 1.376 (3) | C12—C13 | 1.357 (4) |
C6—C7 | 1.391 (3) | C13—C14 | 1.389 (3) |
| | | |
O1—C1—C2 | 122.68 (18) | C7—C8—C8i | 123.9 (3) |
O1—C1—C14 | 121.85 (17) | C7—C8—C9 | 111.88 (17) |
C2—C1—C14 | 114.88 (18) | C8i—C8—C9 | 124.2 (2) |
C1—C2—C3 | 118.56 (17) | C8—C9—C10 | 123.54 (16) |
C1—C2—C7 | 120.07 (16) | C8—C9—C14 | 118.42 (18) |
C3—C2—C7 | 120.96 (16) | C10—C9—C14 | 118.03 (17) |
C2—C3—C4 | 120.39 (19) | C9—C10—C11 | 120.65 (17) |
C3—C4—C5 | 119.13 (18) | C10—C11—C12 | 120.6 (2) |
C4—C5—C6 | 121.47 (18) | C11—C12—C13 | 120.16 (19) |
C5—C6—C7 | 120.30 (18) | C12—C13—C14 | 119.92 (17) |
C2—C7—C6 | 117.64 (16) | C1—C14—C9 | 120.31 (16) |
C2—C7—C8 | 118.55 (16) | C1—C14—C13 | 119.03 (16) |
C6—C7—C8 | 123.80 (17) | C9—C14—C13 | 120.58 (18) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (6.0GPa) topO1—C1 | 1.222 (3) | C7—C8 | 1.491 (3) |
C1—C2 | 1.459 (2) | C8—C8i | 1.359 (4) |
C1—C14 | 1.451 (3) | C8—C9 | 1.490 (3) |
C2—C3 | 1.385 (3) | C9—C10 | 1.388 (3) |
C2—C7 | 1.400 (3) | C9—C14 | 1.407 (3) |
C3—C4 | 1.361 (3) | C10—C11 | 1.367 (3) |
C4—C5 | 1.377 (3) | C11—C12 | 1.382 (3) |
C5—C6 | 1.372 (3) | C12—C13 | 1.356 (3) |
C6—C7 | 1.389 (3) | C13—C14 | 1.389 (3) |
| | | |
O1—C1—C2 | 122.40 (17) | C7—C8—C8i | 124.1 (3) |
O1—C1—C14 | 121.63 (16) | C7—C8—C9 | 111.96 (17) |
C2—C1—C14 | 115.37 (17) | C8i—C8—C9 | 124.0 (2) |
C1—C2—C3 | 118.71 (16) | C8—C9—C10 | 124.12 (16) |
C1—C2—C7 | 119.84 (15) | C8—C9—C14 | 118.39 (17) |
C3—C2—C7 | 120.94 (16) | C10—C9—C14 | 117.47 (17) |
C2—C3—C4 | 120.50 (18) | C9—C10—C11 | 121.14 (17) |
C3—C4—C5 | 119.12 (17) | C10—C11—C12 | 120.66 (19) |
C4—C5—C6 | 121.29 (17) | C11—C12—C13 | 119.72 (19) |
C5—C6—C7 | 120.70 (18) | C12—C13—C14 | 120.46 (16) |
C2—C7—C6 | 117.40 (15) | C1—C14—C9 | 120.14 (16) |
C2—C7—C8 | 118.48 (15) | C1—C14—C13 | 119.31 (15) |
C6—C7—C8 | 124.11 (17) | C9—C14—C13 | 120.42 (18) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (6.5GPa) topO1—C1 | 1.221 (3) | C7—C8 | 1.495 (4) |
C1—C2 | 1.461 (3) | C8—C8i | 1.358 (5) |
C1—C14 | 1.454 (4) | C8—C9 | 1.501 (4) |
C2—C3 | 1.385 (4) | C9—C10 | 1.377 (4) |
C2—C7 | 1.396 (3) | C9—C14 | 1.397 (3) |
C3—C4 | 1.359 (4) | C10—C11 | 1.377 (4) |
C4—C5 | 1.374 (4) | C11—C12 | 1.379 (4) |
C5—C6 | 1.380 (4) | C12—C13 | 1.363 (4) |
C6—C7 | 1.385 (4) | C13—C14 | 1.388 (4) |
| | | |
O1—C1—C2 | 122.6 (2) | C7—C8—C8i | 124.8 (3) |
O1—C1—C14 | 121.5 (2) | C7—C8—C9 | 111.7 (2) |
C2—C1—C14 | 115.1 (2) | C8i—C8—C9 | 123.5 (3) |
C1—C2—C3 | 118.6 (2) | C8—C9—C10 | 123.6 (2) |
C1—C2—C7 | 119.88 (19) | C8—C9—C14 | 118.2 (2) |
C3—C2—C7 | 120.91 (19) | C10—C9—C14 | 118.2 (2) |
C2—C3—C4 | 120.5 (2) | C9—C10—C11 | 120.9 (2) |
C3—C4—C5 | 119.2 (2) | C10—C11—C12 | 120.5 (2) |
C4—C5—C6 | 121.2 (2) | C11—C12—C13 | 119.8 (2) |
C5—C6—C7 | 120.3 (2) | C12—C13—C14 | 120.1 (2) |
C2—C7—C6 | 117.8 (2) | C1—C14—C9 | 120.40 (19) |
C2—C7—C8 | 118.42 (19) | C1—C14—C13 | 119.0 (2) |
C6—C7—C8 | 123.8 (2) | C9—C14—C13 | 120.6 (2) |
Symmetry code: (i) −x+2, −y+1, −z+1. |