The effect of pressure on the crystal structure of bianthrone

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.

Computing details

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).

Figures

(ambient)

Crystal data

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) Å^3	0.57 × 0.33 × 0.31 mm
Z = 2

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.2193 (17)	C7—C8	1.490 (2)
C1—C2	1.481 (2)	C8—C8^i	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—C8^i	123.56 (16)
O1—C1—C14	121.83 (15)	C7—C8—C9	112.11 (11)
C2—C1—C14	115.12 (12)	C8^i—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.

(1.2GPa)

Crystal data

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) Å^3	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.223 (2)	C7—C8	1.493 (3)
C1—C2	1.476 (3)	C8—C8^i	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—C8^i	123.8 (3)
O1—C1—C14	121.69 (17)	C7—C8—C9	111.83 (16)
C2—C1—C14	115.29 (16)	C8^i—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.

(2.2GPa)

Crystal data

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) Å^3	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.225 (2)	C7—C8	1.494 (3)
C1—C2	1.473 (3)	C8—C8^i	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—C8^i	124.2 (3)
O1—C1—C14	121.78 (17)	C7—C8—C9	111.79 (17)
C2—C1—C14	115.24 (17)	C8^i—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.

(3.3GPa)

Crystal data

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) Å^3	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.220 (3)	C7—C8	1.493 (3)
C1—C2	1.471 (3)	C8—C8^i	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—C8^i	124.1 (3)
O1—C1—C14	121.84 (17)	C7—C8—C9	112.07 (17)
C2—C1—C14	115.12 (17)	C8^i—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.

(4.2GPa)

Crystal data

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) Å^3	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.221 (2)	C7—C8	1.491 (3)
C1—C2	1.469 (2)	C8—C8^i	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—C8^i	124.3 (2)
O1—C1—C14	121.86 (15)	C7—C8—C9	111.76 (16)
C2—C1—C14	114.69 (17)	C8^i—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.

(5.1GPa)

Crystal data

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) Å^3	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.221 (3)	C7—C8	1.492 (3)
C1—C2	1.465 (3)	C8—C8^i	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—C8^i	123.9 (3)
O1—C1—C14	121.85 (17)	C7—C8—C9	111.88 (17)
C2—C1—C14	114.88 (18)	C8^i—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.

(6.0GPa)

Crystal data

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) Å^3	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.222 (3)	C7—C8	1.491 (3)
C1—C2	1.459 (2)	C8—C8^i	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—C8^i	124.1 (3)
O1—C1—C14	121.63 (16)	C7—C8—C9	111.96 (17)
C2—C1—C14	115.37 (17)	C8^i—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.

(6.5GPa)

Crystal data

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) Å^3	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.221 (3)	C7—C8	1.495 (4)
C1—C2	1.461 (3)	C8—C8^i	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—C8^i	124.8 (3)
O1—C1—C14	121.5 (2)	C7—C8—C9	111.7 (2)
C2—C1—C14	115.1 (2)	C8^i—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.