Monitoring structural transformations in crystals. 12. Course of an intramolecular [4 + 4] photo­cycloaddition in a crystal

Variations in crystal and molecular structures, brought about by the intramolecular [4 + 4] photocycloaddition of bi(anthracene-9,10-dimethylene), were monitored using X-ray diffraction. The cell volume increased by 0.8% until the reaction was ca 40% complete, and afterwards decreased by 1.6% during the remainder of the photoreaction. The changes of the a and b lattice parameters were correlated with the changes of the molecular shape and packing. The distance between the directly reacting C atoms varied in a manner not observed for other photochemical reactions in crystals. It was constant until ca 20% photoreaction progress, then decreased, and later stabilized from ca 40% photoreaction progress. This phenomenon was explained by interplay between stress resulting from the presence of product molecules and the rigidity of reactant molecules. Changes of the orientation of molecules during the photoreaction were smaller than in the case of other monitored photochemical reactions in crystals owing to similarities in the shape and packing of reactant and product molecules. Weak C—H...π hydrogen bonds exist among reactant molecules in the pure reactant and partly reacted crystals.

Computing details

Data collection: CRYSALIS (Oxford Diffraction, 2003) for (0P), 4.3P, 9.9P, 14.6P, 16.2P, 18.3P, 32.4P, 38.6P, 84.6P; Kuma KM4CCD software 2000 for 63.9P, 100P. For all compounds, cell refinement: CRYSALIS (Oxford Diffraction, 2003); data reduction: CRYSALIS (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

(0P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.329 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.266 (2) Å	Cell parameters from 1000 reflections
b = 12.773 (2) Å	θ = 3–27°
c = 8.4459 (16) Å	µ = 0.08 mm^−1
β = 112.86 (2)°	T = 299 K
V = 1020.5 (3) Å^3	Plate, orange
Z = 2	0.55 × 0.33 × 0.15 mm

Data collection

Kuma KM4CCD diffractometer	1315 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→12
5375 measured reflections	k = −15→11
1783 independent reflections	l = −9→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
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) = 0.121	w = 1/[σ^2(Fo^2) + (0.0641P)^2 + 0.2043P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1783 reflections	Δρmax = 0.20 e Å^−3
146 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (6)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1R	0.33221 (19)	0.56799 (15)	0.8253 (2)	0.0585 (5)
H1R	0.3694	0.5169	0.9094	0.070*
C2R	0.4208 (2)	0.63661 (16)	0.7987 (3)	0.0677 (6)
H2R	0.5167	0.6346	0.8678	0.081*
C3R	0.3700 (2)	0.71015 (16)	0.6690 (3)	0.0665 (6)
H3R	0.4322	0.7572	0.6513	0.080*
C4R	0.2306 (2)	0.71437 (13)	0.5677 (2)	0.0557 (5)
H4R	0.1995	0.7624	0.4780	0.067*
C5R	−0.2551 (2)	0.62601 (15)	0.4930 (3)	0.0605 (5)
H5R	−0.2926	0.6726	0.4018	0.073*
C6R	−0.3416 (2)	0.58108 (19)	0.5596 (3)	0.0771 (7)
H6R	−0.4367	0.5995	0.5174	0.093*
C7R	−0.2895 (3)	0.5067 (2)	0.6919 (3)	0.0804 (7)
H7R	−0.3503	0.4760	0.7363	0.097*
C8R	−0.1514 (2)	0.47938 (16)	0.7552 (2)	0.0651 (6)
H8R	−0.1191	0.4281	0.8397	0.078*
C9R	0.08859 (17)	0.50080 (12)	0.75868 (18)	0.0441 (4)
C10R	−0.01637 (18)	0.65106 (11)	0.4943 (2)	0.0426 (4)
C11R	−0.10858 (17)	0.60372 (12)	0.5592 (2)	0.0446 (4)
C12R	−0.05477 (18)	0.52768 (12)	0.69495 (19)	0.0458 (4)
C13R	0.18260 (17)	0.57055 (12)	0.72886 (18)	0.0428 (4)
C14R	0.12930 (17)	0.64705 (11)	0.59462 (19)	0.0422 (4)
C15R	−0.0724 (2)	0.69401 (13)	0.3137 (2)	0.0546 (5)
H15C	0.0034	0.7304	0.2951	0.066*
H15D	−0.1459	0.7448	0.3019	0.066*
C16R	0.1337 (2)	0.39144 (13)	0.8273 (2)	0.0581 (5)
H16C	0.1023	0.3777	0.9198	0.070*
H16D	0.2361	0.3874	0.8744	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.0601 (12)	0.0551 (11)	0.0495 (10)	0.0084 (9)	0.0094 (9)	−0.0028 (8)
C2R	0.0532 (12)	0.0710 (13)	0.0727 (13)	−0.0049 (10)	0.0175 (10)	−0.0111 (11)
C3R	0.0597 (13)	0.0688 (13)	0.0744 (13)	−0.0130 (10)	0.0300 (11)	−0.0115 (11)
C4R	0.0756 (13)	0.0437 (9)	0.0526 (10)	−0.0040 (8)	0.0303 (10)	−0.0005 (8)
C5R	0.0550 (12)	0.0587 (11)	0.0616 (11)	−0.0008 (9)	0.0157 (9)	−0.0194 (9)
C6R	0.0524 (12)	0.0896 (16)	0.0861 (16)	−0.0132 (11)	0.0233 (12)	−0.0386 (14)
C7R	0.0810 (17)	0.0962 (17)	0.0791 (15)	−0.0366 (13)	0.0475 (13)	−0.0320 (14)
C8R	0.0808 (15)	0.0676 (12)	0.0542 (11)	−0.0239 (11)	0.0342 (11)	−0.0134 (9)
C9R	0.0612 (11)	0.0405 (9)	0.0263 (7)	−0.0012 (8)	0.0121 (7)	−0.0014 (6)
C10R	0.0594 (11)	0.0286 (7)	0.0385 (8)	0.0043 (7)	0.0176 (8)	−0.0013 (6)
C11R	0.0519 (10)	0.0380 (8)	0.0399 (8)	0.0009 (7)	0.0133 (7)	−0.0127 (7)
C12R	0.0637 (11)	0.0403 (9)	0.0351 (8)	−0.0103 (8)	0.0212 (8)	−0.0099 (7)
C13R	0.0557 (10)	0.0366 (8)	0.0333 (8)	0.0019 (7)	0.0142 (7)	−0.0053 (6)
C14R	0.0566 (10)	0.0333 (8)	0.0387 (8)	0.0022 (7)	0.0206 (8)	−0.0040 (6)
C15R	0.0701 (12)	0.0400 (9)	0.0460 (10)	0.0063 (8)	0.0142 (9)	0.0088 (7)
C16R	0.0786 (13)	0.0466 (10)	0.0368 (9)	−0.0027 (9)	0.0089 (9)	0.0087 (7)

Geometric parameters (Å, º)

C1R—C2R	1.343 (3)	C9R—C12R	1.399 (2)
C1R—C13R	1.432 (2)	C9R—C13R	1.406 (2)
C2R—C3R	1.382 (3)	C9R—C16R	1.514 (2)
C3R—C4R	1.354 (3)	C10R—C11R	1.402 (2)
C4R—C14R	1.434 (2)	C10R—C14R	1.404 (2)
C5R—C6R	1.350 (3)	C10R—C15R	1.509 (2)
C5R—C11R	1.415 (2)	C11R—C12R	1.439 (2)
C6R—C7R	1.405 (3)	C13R—C14R	1.435 (2)
C7R—C8R	1.352 (3)	C15R—C16R^i	1.557 (2)
C8R—C12R	1.420 (2)	C16R—C15R^i	1.557 (2)
C2R—C1R—C13R	122.42 (18)	C10R—C11R—C5R	122.32 (16)
C1R—C2R—C3R	120.29 (19)	C10R—C11R—C12R	119.61 (15)
C4R—C3R—C2R	120.59 (18)	C5R—C11R—C12R	118.05 (16)
C3R—C4R—C14R	121.99 (17)	C9R—C12R—C8R	122.16 (16)
C6R—C5R—C11R	121.4 (2)	C9R—C12R—C11R	119.53 (14)
C5R—C6R—C7R	120.6 (2)	C8R—C12R—C11R	118.27 (17)
C8R—C7R—C6R	120.4 (2)	C9R—C13R—C1R	122.88 (15)
C7R—C8R—C12R	121.2 (2)	C9R—C13R—C14R	119.70 (15)
C12R—C9R—C13R	117.92 (14)	C1R—C13R—C14R	117.41 (15)
C12R—C9R—C16R	119.54 (15)	C10R—C14R—C4R	123.39 (15)
C13R—C9R—C16R	121.60 (15)	C10R—C14R—C13R	119.44 (14)
C11R—C10R—C14R	118.10 (14)	C4R—C14R—C13R	117.15 (16)
C11R—C10R—C15R	120.12 (15)	C10R—C15R—C16R^i	113.62 (13)
C14R—C10R—C15R	121.44 (15)	C9R—C16R—C15R^i	112.41 (13)

Symmetry code: (i) −x, −y+1, −z+1.

(4.3P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.330 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.274 (2) Å	Cell parameters from 1000 reflections
b = 12.774 (2) Å	θ = 3–27°
c = 8.446 (2) Å	µ = 0.08 mm^−1
β = 112.99 (3)°	T = 299 K
V = 1020.4 (4) Å^3	Plate, orange
Z = 2	0.55 × 0.33 × 0.15 mm

Data collection

Kuma KM4CCD diffractometer	1310 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→12
5357 measured reflections	k = −15→11
1784 independent reflections	l = −10→9

Refinement

Refinement on F^2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0697P)^2 + 0.1646P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1784 reflections	Δρmax = 0.20 e Å^−3
211 parameters	Δρmin = −0.16 e Å^−3
206 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (7)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.286 (3)	0.542 (4)	0.847 (5)	0.059 (12)*	0.043 (4)
H1P	0.3064	0.4921	0.9338	0.071*	0.043 (4)
C2P	0.392 (3)	0.607 (4)	0.842 (6)	0.059 (12)*	0.043 (4)
H2P	0.4830	0.6006	0.9246	0.071*	0.043 (4)
C3P	0.362 (4)	0.680 (4)	0.715 (7)	0.056 (12)*	0.043 (4)
H3P	0.4342	0.7235	0.7119	0.067*	0.043 (4)
C4P	0.228 (4)	0.691 (5)	0.592 (7)	0.054 (7)*	0.043 (4)
H4P	0.2099	0.7418	0.5069	0.064*	0.043 (4)
C5P	−0.266 (4)	0.652 (5)	0.468 (7)	0.052 (7)*	0.043 (4)
H5P	−0.2887	0.7017	0.3815	0.062*	0.043 (4)
C6P	−0.367 (4)	0.623 (5)	0.532 (7)	0.066 (7)*	0.043 (4)
H6P	−0.4557	0.6543	0.4891	0.080*	0.043 (4)
C7P	−0.334 (4)	0.550 (5)	0.660 (8)	0.073 (7)*	0.043 (4)
H7P	−0.4016	0.5296	0.7008	0.088*	0.043 (4)
C8P	−0.200 (5)	0.505 (5)	0.728 (8)	0.058 (7)*	0.043 (4)
H8P	−0.1772	0.4594	0.8198	0.070*	0.043 (4)
C9P	0.036 (3)	0.4695 (16)	0.696 (3)	0.049 (7)*	0.043 (4)
C10P	−0.026 (3)	0.6203 (19)	0.451 (3)	0.053 (12)*	0.043 (4)
C11P	−0.133 (4)	0.606 (3)	0.532 (5)	0.039 (7)*	0.043 (4)
C12P	−0.100 (4)	0.529 (3)	0.660 (5)	0.043 (7)*	0.043 (4)
C13P	0.151 (3)	0.549 (2)	0.724 (4)	0.038 (7)*	0.043 (4)
C14P	0.119 (4)	0.628 (3)	0.595 (4)	0.050 (13)*	0.043 (4)
C15P	−0.062 (6)	0.7011 (18)	0.306 (4)	0.047 (7)*	0.043 (4)
H15A	−0.1523	0.7349	0.2795	0.056*	0.043 (4)
H15B	0.0120	0.7531	0.3263	0.056*	0.043 (4)
C16P	0.065 (5)	0.378 (3)	0.824 (3)	0.044 (7)*	0.043 (4)
H16A	0.1565	0.3832	0.9190	0.053*	0.043 (4)
H16B	−0.0092	0.3686	0.8666	0.053*	0.043 (4)
C1R	0.3310 (3)	0.5680 (2)	0.8258 (3)	0.0584 (7)	0.957 (4)
H1R	0.3680	0.5168	0.9099	0.070*	0.957 (4)
C2R	0.4202 (3)	0.6370 (2)	0.7996 (4)	0.0689 (8)	0.957 (4)
H2R	0.5161	0.6351	0.8691	0.083*	0.957 (4)
C3R	0.3690 (3)	0.7106 (3)	0.6695 (4)	0.0685 (8)	0.957 (4)
H3R	0.4310	0.7578	0.6519	0.082*	0.957 (4)
C4R	0.2295 (3)	0.7146 (2)	0.5677 (4)	0.0580 (7)	0.957 (4)
H4R	0.1983	0.7625	0.4777	0.070*	0.957 (4)
C5R	−0.2554 (3)	0.6256 (2)	0.4929 (4)	0.0622 (7)	0.957 (4)
H5R	−0.2930	0.6719	0.4013	0.075*	0.957 (4)
C6R	−0.3418 (3)	0.5810 (3)	0.5597 (5)	0.0785 (9)	0.957 (4)
H6R	−0.4368	0.5997	0.5178	0.094*	0.957 (4)
C7R	−0.2896 (4)	0.5066 (3)	0.6915 (4)	0.0807 (10)	0.957 (4)
H7R	−0.3505	0.4759	0.7356	0.097*	0.957 (4)
C8R	−0.1513 (3)	0.4791 (2)	0.7553 (4)	0.0655 (8)	0.957 (4)
H8R	−0.1191	0.4277	0.8397	0.079*	0.957 (4)
C9R	0.0879 (2)	0.50083 (15)	0.7588 (2)	0.0451 (6)	0.957 (4)
C10R	−0.0168 (2)	0.65111 (15)	0.4944 (3)	0.0433 (6)	0.957 (4)
C11R	−0.1089 (3)	0.60348 (19)	0.5592 (3)	0.0464 (6)	0.957 (4)
C12R	−0.0547 (3)	0.52762 (17)	0.6952 (3)	0.0460 (6)	0.957 (4)
C13R	0.1825 (3)	0.57080 (18)	0.7292 (3)	0.0436 (6)	0.957 (4)
C14R	0.1285 (3)	0.64717 (19)	0.5945 (3)	0.0430 (6)	0.957 (4)
C15R	−0.0736 (4)	0.69380 (18)	0.3133 (3)	0.0578 (8)	0.957 (4)
H15C	0.0017	0.7309	0.2949	0.069*	0.957 (4)
H15D	−0.1478	0.7439	0.3012	0.069*	0.957 (4)
C16R	0.1337 (3)	0.39168 (17)	0.8281 (3)	0.0574 (7)	0.957 (4)
H16C	0.1018	0.3777	0.9200	0.069*	0.957 (4)
H16D	0.2361	0.3881	0.8762	0.069*	0.957 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.0598 (16)	0.0530 (14)	0.0529 (14)	0.0044 (13)	0.0116 (12)	−0.0033 (11)
C2R	0.0548 (16)	0.0713 (17)	0.0734 (18)	−0.0042 (14)	0.0172 (14)	−0.0093 (15)
C3R	0.0651 (18)	0.0680 (19)	0.076 (2)	−0.0144 (13)	0.0318 (15)	−0.0086 (15)
C4R	0.0826 (19)	0.0428 (15)	0.0555 (15)	−0.0031 (12)	0.0346 (13)	0.0011 (10)
C5R	0.0593 (16)	0.0562 (18)	0.0631 (17)	0.0004 (12)	0.0152 (13)	−0.0182 (13)
C6R	0.0548 (16)	0.085 (2)	0.090 (2)	−0.0112 (15)	0.0224 (16)	−0.035 (2)
C7R	0.077 (2)	0.095 (2)	0.082 (2)	−0.0327 (19)	0.0452 (18)	−0.0293 (18)
C8R	0.081 (2)	0.0658 (18)	0.0567 (16)	−0.0211 (15)	0.0344 (16)	−0.0125 (12)
C9R	0.0625 (14)	0.0397 (11)	0.0274 (11)	−0.0032 (10)	0.0112 (10)	−0.0020 (8)
C10R	0.0631 (15)	0.0269 (10)	0.0389 (11)	0.0045 (9)	0.0187 (10)	−0.0015 (9)
C11R	0.0537 (14)	0.0392 (11)	0.0407 (12)	0.0026 (10)	0.0123 (11)	−0.0130 (9)
C12R	0.0625 (16)	0.0421 (11)	0.0347 (11)	−0.0101 (11)	0.0204 (11)	−0.0104 (9)
C13R	0.0564 (14)	0.0362 (11)	0.0360 (11)	0.0002 (10)	0.0155 (10)	−0.0053 (8)
C14R	0.0593 (15)	0.0316 (11)	0.0401 (11)	0.0016 (9)	0.0217 (10)	−0.0043 (8)
C15R	0.0769 (18)	0.0399 (11)	0.0498 (13)	0.0077 (11)	0.0175 (12)	0.0101 (10)
C16R	0.0758 (18)	0.0459 (12)	0.0384 (11)	−0.0035 (12)	0.0092 (11)	0.0089 (9)

Geometric parameters (Å, º)

C1P—C13P	1.371 (19)	C16P—C15P^i	1.484 (9)
C1P—C2P	1.38 (2)	C1R—C2R	1.350 (3)
C2P—C3P	1.366 (12)	C1R—C13R	1.423 (3)
C3P—C4P	1.368 (12)	C2R—C3R	1.385 (4)
C4P—C14P	1.392 (19)	C3R—C4R	1.354 (4)
C5P—C6P	1.39 (2)	C4R—C14R	1.433 (3)
C5P—C11P	1.392 (19)	C5R—C6R	1.350 (4)
C6P—C7P	1.366 (12)	C5R—C11R	1.414 (3)
C7P—C8P	1.39 (2)	C6R—C7R	1.401 (4)
C8P—C12P	1.392 (19)	C7R—C8R	1.355 (4)
C9P—C13P	1.510 (16)	C8R—C12R	1.421 (3)
C9P—C12P	1.511 (16)	C9R—C12R	1.392 (3)
C9P—C16P	1.539 (12)	C9R—C13R	1.413 (3)
C9P—C10P^i	1.665 (9)	C9R—C16R	1.514 (3)
C10P—C11P	1.513 (17)	C10R—C14R	1.401 (3)
C10P—C14P	1.515 (17)	C10R—C11R	1.403 (3)
C10P—C15P	1.535 (18)	C10R—C15R	1.510 (3)
C10P—C9P^i	1.665 (9)	C11R—C12R	1.438 (3)
C11P—C12P	1.403 (18)	C13R—C14R	1.435 (3)
C13P—C14P	1.418 (18)	C15R—C16R^i	1.557 (3)
C15P—C16P^i	1.484 (9)	C16R—C15R^i	1.557 (3)
C13P—C1P—C2P	120.4 (17)	C13P—C14P—C10P	115.6 (14)
C3P—C2P—C1P	120.2 (17)	C16P^i—C15P—C10P	93.5 (9)
C2P—C3P—C4P	120.8 (17)	C15P^i—C16P—C9P	93.2 (9)
C3P—C4P—C14P	120.3 (17)	C2R—C1R—C13R	122.3 (2)
C6P—C5P—C11P	120.7 (17)	C1R—C2R—C3R	120.1 (3)
C7P—C6P—C5P	119.6 (17)	C4R—C3R—C2R	120.6 (3)
C6P—C7P—C8P	120.6 (18)	C3R—C4R—C14R	121.9 (2)
C7P—C8P—C12P	120.9 (17)	C6R—C5R—C11R	121.5 (3)
C13P—C9P—C12P	107.4 (13)	C5R—C6R—C7R	120.6 (3)
C13P—C9P—C16P	118.4 (16)	C8R—C7R—C6R	120.5 (3)
C12P—C9P—C16P	115.7 (16)	C7R—C8R—C12R	121.0 (3)
C13P—C9P—C10P^i	113.6 (16)	C12R—C9R—C13R	118.00 (18)
C12P—C9P—C10P^i	114.3 (16)	C12R—C9R—C16R	119.8 (2)
C16P—C9P—C10P^i	86.6 (7)	C13R—C9R—C16R	121.3 (2)
C11P—C10P—C14P	107.9 (14)	C14R—C10R—C11R	118.08 (19)
C11P—C10P—C15P	116.9 (18)	C14R—C10R—C15R	121.6 (2)
C14P—C10P—C15P	117.0 (18)	C11R—C10R—C15R	120.0 (2)
C11P—C10P—C9P^i	114.1 (16)	C10R—C11R—C5R	122.3 (2)
C14P—C10P—C9P^i	113.3 (16)	C10R—C11R—C12R	119.6 (2)
C15P—C10P—C9P^i	86.6 (7)	C5R—C11R—C12R	118.1 (2)
C5P—C11P—C12P	119.7 (15)	C9R—C12R—C8R	122.1 (2)
C5P—C11P—C10P	123.7 (17)	C9R—C12R—C11R	119.62 (19)
C12P—C11P—C10P	115.7 (14)	C8R—C12R—C11R	118.2 (2)
C8P—C12P—C11P	118.3 (15)	C9R—C13R—C1R	122.71 (19)
C8P—C12P—C9P	125.6 (16)	C9R—C13R—C14R	119.4 (2)
C11P—C12P—C9P	115.6 (14)	C1R—C13R—C14R	117.9 (2)
C1P—C13P—C14P	119.5 (15)	C10R—C14R—C4R	123.4 (2)
C1P—C13P—C9P	124.6 (16)	C10R—C14R—C13R	119.6 (2)
C14P—C13P—C9P	115.1 (14)	C4R—C14R—C13R	117.0 (2)
C4P—C14P—C13P	118.7 (15)	C10R—C15R—C16R^i	113.85 (18)
C4P—C14P—C10P	124.7 (17)	C9R—C16R—C15R^i	112.25 (17)

Symmetry code: (i) −x, −y+1, −z+1.

(9.9P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.327 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.285 (2) Å	Cell parameters from 1000 reflections
b = 12.791 (2) Å	θ = 3–27°
c = 8.4484 (18) Å	µ = 0.08 mm^−1
β = 113.05 (3)°	T = 299 K
V = 1022.7 (3) Å^3	Plate, orange
Z = 2	0.55 × 0.33 × 0.15 mm

Data collection

Kuma KM4CCD diffractometer	1291 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→12
5204 measured reflections	k = −15→11
1786 independent reflections	l = −10→9

Refinement

Refinement on F^2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0761P)^2 + 0.2388P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1786 reflections	Δρmax = 0.18 e Å^−3
211 parameters	Δρmin = −0.16 e Å^−3
200 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (9)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.284 (2)	0.547 (2)	0.851 (3)	0.077 (10)*	0.099 (6)
H1P	0.3047	0.4988	0.9394	0.092*	0.099 (6)
C2P	0.387 (3)	0.615 (3)	0.846 (4)	0.067 (9)*	0.099 (6)
H2P	0.4778	0.6112	0.9315	0.081*	0.099 (6)
C3P	0.357 (3)	0.688 (3)	0.719 (4)	0.068 (10)*	0.099 (6)
H3P	0.4285	0.7321	0.7167	0.082*	0.099 (6)
C4P	0.224 (3)	0.696 (3)	0.593 (5)	0.058 (6)*	0.099 (6)
H4P	0.2052	0.7461	0.5069	0.070*	0.099 (6)
C5P	−0.268 (3)	0.650 (3)	0.467 (5)	0.054 (6)*	0.099 (6)
H5P	−0.2897	0.7008	0.3814	0.065*	0.099 (6)
C6P	−0.369 (3)	0.620 (3)	0.528 (4)	0.066 (6)*	0.099 (6)
H6P	−0.4585	0.6495	0.4828	0.079*	0.099 (6)
C7P	−0.335 (3)	0.547 (3)	0.656 (4)	0.068 (7)*	0.099 (6)
H7P	−0.4036	0.5249	0.6944	0.081*	0.099 (6)
C8P	−0.201 (3)	0.504 (3)	0.728 (5)	0.058 (7)*	0.099 (6)
H8P	−0.1781	0.4587	0.8206	0.069*	0.099 (6)
C9P	0.038 (2)	0.4712 (11)	0.695 (2)	0.065 (8)*	0.099 (6)
C10P	−0.028 (2)	0.6190 (15)	0.451 (2)	0.067 (10)*	0.099 (6)
C11P	−0.134 (3)	0.606 (3)	0.534 (4)	0.043 (6)*	0.099 (6)
C12P	−0.099 (3)	0.530 (2)	0.663 (4)	0.044 (6)*	0.099 (6)
C13P	0.151 (2)	0.5513 (18)	0.723 (3)	0.042 (13)*	0.099 (6)
C14P	0.117 (3)	0.630 (2)	0.594 (3)	0.058 (12)*	0.099 (6)
C15P	−0.065 (5)	0.6992 (14)	0.305 (3)	0.049 (6)*	0.099 (6)
H15A	−0.1566	0.7319	0.2770	0.058*	0.099 (6)
H15B	0.0073	0.7519	0.3245	0.058*	0.099 (6)
C16P	0.066 (3)	0.3806 (15)	0.823 (2)	0.041 (5)*	0.099 (6)
H16A	0.1571	0.3863	0.9193	0.049*	0.099 (6)
H16B	−0.0086	0.3708	0.8644	0.049*	0.099 (6)
C1R	0.3294 (4)	0.5680 (3)	0.8282 (4)	0.0612 (9)	0.901 (6)
H1R	0.3660	0.5174	0.9132	0.073*	0.901 (6)
C2R	0.4192 (4)	0.6375 (3)	0.8014 (5)	0.0720 (10)	0.901 (6)
H2R	0.5151	0.6355	0.8709	0.086*	0.901 (6)
C3R	0.3681 (4)	0.7108 (3)	0.6710 (6)	0.0716 (10)	0.901 (6)
H3R	0.4301	0.7580	0.6536	0.086*	0.901 (6)
C4R	0.2284 (5)	0.7145 (3)	0.5684 (6)	0.0621 (10)	0.901 (6)
H4R	0.1973	0.7623	0.4784	0.075*	0.901 (6)
C5R	−0.2562 (4)	0.6257 (3)	0.4927 (6)	0.0661 (10)	0.901 (6)
H5R	−0.2937	0.6723	0.4014	0.079*	0.901 (6)
C6R	−0.3429 (4)	0.5814 (4)	0.5590 (6)	0.0819 (12)	0.901 (6)
H6R	−0.4378	0.6001	0.5168	0.098*	0.901 (6)
C7R	−0.2904 (5)	0.5070 (4)	0.6914 (6)	0.0838 (13)	0.901 (6)
H7R	−0.3511	0.4766	0.7356	0.101*	0.901 (6)
C8R	−0.1525 (5)	0.4792 (3)	0.7552 (5)	0.0678 (10)	0.901 (6)
H8R	−0.1205	0.4280	0.8398	0.081*	0.901 (6)
C9R	0.0863 (3)	0.5007 (2)	0.7584 (3)	0.0484 (8)	0.901 (6)
C10R	−0.0169 (3)	0.6508 (2)	0.4939 (4)	0.0458 (8)	0.901 (6)
C11R	−0.1098 (4)	0.6033 (3)	0.5583 (5)	0.0489 (9)	0.901 (6)
C12R	−0.0556 (4)	0.5274 (2)	0.6945 (4)	0.0489 (8)	0.901 (6)
C13R	0.1812 (5)	0.5707 (3)	0.7297 (4)	0.0461 (9)	0.901 (6)
C14R	0.1270 (4)	0.6466 (3)	0.5946 (4)	0.0454 (10)	0.901 (6)
C15R	−0.0743 (6)	0.6931 (2)	0.3129 (5)	0.0614 (12)	0.901 (6)
H15C	0.0003	0.7310	0.2947	0.074*	0.901 (6)
H15D	−0.1492	0.7425	0.3008	0.074*	0.901 (6)
C16R	0.1333 (5)	0.3919 (2)	0.8292 (3)	0.0582 (9)	0.901 (6)
H16C	0.1007	0.3776	0.9204	0.070*	0.901 (6)
H16D	0.2357	0.3888	0.8781	0.070*	0.901 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.065 (2)	0.0537 (18)	0.0527 (18)	0.0029 (18)	0.0096 (16)	−0.0043 (14)
C2R	0.057 (2)	0.073 (2)	0.079 (2)	−0.0064 (17)	0.019 (2)	−0.009 (2)
C3R	0.071 (2)	0.069 (2)	0.078 (3)	−0.0153 (17)	0.032 (2)	−0.007 (2)
C4R	0.092 (3)	0.0428 (19)	0.060 (2)	−0.0030 (15)	0.0389 (18)	0.0017 (14)
C5R	0.065 (2)	0.057 (2)	0.067 (2)	0.0016 (16)	0.0161 (17)	−0.0186 (18)
C6R	0.056 (2)	0.085 (3)	0.097 (3)	−0.010 (2)	0.022 (2)	−0.030 (3)
C7R	0.076 (3)	0.098 (3)	0.089 (3)	−0.030 (3)	0.045 (2)	−0.026 (2)
C8R	0.085 (3)	0.066 (2)	0.060 (2)	−0.020 (2)	0.037 (2)	−0.0124 (16)
C9R	0.0672 (19)	0.0408 (14)	0.0302 (14)	−0.0022 (13)	0.0116 (13)	0.0001 (11)
C10R	0.068 (2)	0.0269 (13)	0.0430 (15)	0.0064 (11)	0.0217 (13)	−0.0003 (12)
C11R	0.0556 (19)	0.0414 (15)	0.0441 (17)	0.0029 (13)	0.0133 (15)	−0.0124 (12)
C12R	0.068 (2)	0.0432 (15)	0.0369 (15)	−0.0105 (15)	0.0224 (17)	−0.0110 (11)
C13R	0.060 (2)	0.0359 (15)	0.0406 (18)	−0.0003 (16)	0.0178 (14)	−0.0057 (12)
C14R	0.065 (2)	0.0319 (14)	0.0426 (16)	0.0034 (12)	0.0245 (14)	−0.0027 (11)
C15R	0.085 (3)	0.0412 (15)	0.0519 (18)	0.0104 (14)	0.0204 (16)	0.0112 (12)
C16R	0.074 (2)	0.0480 (16)	0.0412 (15)	−0.0046 (15)	0.0097 (14)	0.0101 (12)

Geometric parameters (Å, º)

C1P—C13P	1.372 (18)	C16P—C15P^i	1.483 (9)
C1P—C2P	1.383 (19)	C1R—C2R	1.363 (5)
C2P—C3P	1.366 (12)	C1R—C13R	1.422 (5)
C3P—C4P	1.369 (12)	C2R—C3R	1.384 (6)
C4P—C14P	1.394 (18)	C3R—C4R	1.357 (5)
C5P—C6P	1.380 (19)	C4R—C14R	1.439 (5)
C5P—C11P	1.391 (18)	C5R—C6R	1.349 (4)
C6P—C7P	1.369 (12)	C5R—C11R	1.415 (5)
C7P—C8P	1.382 (19)	C6R—C7R	1.405 (6)
C8P—C12P	1.396 (18)	C7R—C8R	1.352 (5)
C9P—C13P	1.498 (15)	C8R—C12R	1.427 (4)
C9P—C12P	1.520 (16)	C9R—C12R	1.386 (5)
C9P—C16P	1.535 (11)	C9R—C13R	1.414 (5)
C9P—C10P^i	1.665 (9)	C9R—C16R	1.517 (4)
C10P—C11P	1.511 (16)	C10R—C14R	1.390 (4)
C10P—C14P	1.516 (16)	C10R—C11R	1.409 (4)
C10P—C15P	1.538 (18)	C10R—C15R	1.507 (4)
C10P—C9P^i	1.665 (9)	C11R—C12R	1.441 (4)
C11P—C12P	1.403 (18)	C13R—C14R	1.434 (4)
C13P—C14P	1.420 (18)	C15R—C16R^i	1.556 (4)
C15P—C16P^i	1.483 (9)	C16R—C15R^i	1.556 (4)
C13P—C1P—C2P	119.7 (16)	C13P—C14P—C10P	114.5 (13)
C3P—C2P—C1P	120.8 (16)	C16P^i—C15P—C10P	93.2 (9)
C2P—C3P—C4P	120.8 (16)	C15P^i—C16P—C9P	93.5 (9)
C3P—C4P—C14P	120.0 (16)	C2R—C1R—C13R	121.8 (3)
C6P—C5P—C11P	120.4 (16)	C1R—C2R—C3R	120.2 (3)
C7P—C6P—C5P	119.4 (16)	C4R—C3R—C2R	120.6 (4)
C6P—C7P—C8P	121.2 (17)	C3R—C4R—C14R	122.1 (3)
C7P—C8P—C12P	120.6 (16)	C6R—C5R—C11R	121.8 (4)
C13P—C9P—C12P	107.3 (12)	C5R—C6R—C7R	120.3 (4)
C13P—C9P—C16P	118.8 (14)	C8R—C7R—C6R	120.8 (3)
C12P—C9P—C16P	113.9 (13)	C7R—C8R—C12R	121.0 (4)
C13P—C9P—C10P^i	114.1 (14)	C12R—C9R—C13R	118.0 (2)
C12P—C9P—C10P^i	115.5 (14)	C12R—C9R—C16R	120.2 (3)
C16P—C9P—C10P^i	86.6 (7)	C13R—C9R—C16R	121.0 (3)
C11P—C10P—C14P	107.8 (14)	C14R—C10R—C11R	117.9 (3)
C11P—C10P—C15P	116.7 (17)	C14R—C10R—C15R	122.3 (3)
C14P—C10P—C15P	116.0 (17)	C11R—C10R—C15R	119.4 (3)
C11P—C10P—C9P^i	114.8 (15)	C10R—C11R—C5R	122.7 (3)
C14P—C10P—C9P^i	114.1 (15)	C10R—C11R—C12R	119.3 (3)
C15P—C10P—C9P^i	86.6 (7)	C5R—C11R—C12R	118.0 (3)
C5P—C11P—C12P	120.6 (14)	C9R—C12R—C8R	122.1 (3)
C5P—C11P—C10P	123.1 (15)	C9R—C12R—C11R	119.8 (3)
C12P—C11P—C10P	115.3 (13)	C8R—C12R—C11R	118.1 (3)
C8P—C12P—C11P	117.7 (13)	C9R—C13R—C1R	122.5 (3)
C8P—C12P—C9P	126.9 (15)	C9R—C13R—C14R	119.1 (3)
C11P—C12P—C9P	114.5 (13)	C1R—C13R—C14R	118.4 (4)
C1P—C13P—C14P	119.9 (14)	C10R—C14R—C13R	120.1 (3)
C1P—C13P—C9P	124.9 (15)	C10R—C14R—C4R	123.1 (3)
C14P—C13P—C9P	114.9 (13)	C13R—C14R—C4R	116.8 (3)
C4P—C14P—C13P	118.7 (14)	C10R—C15R—C16R^i	114.3 (3)
C4P—C14P—C10P	125.8 (16)	C9R—C16R—C15R^i	111.7 (2)

Symmetry code: (i) −x, −y+1, −z+1.

(14.6P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2848 (19) Å	Cell parameters from 1000 reflections
b = 12.8104 (18) Å	θ = 3–27°
c = 8.4443 (15) Å	µ = 0.08 mm^−1
β = 113.05 (2)°	T = 299 K
V = 1023.7 (3) Å^3	Plate, orange
Z = 2	0.55 × 0.33 × 0.15 mm

Data collection

Kuma KM4CCD diffractometer	1264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→12
5257 measured reflections	k = −15→12
1788 independent reflections	l = −9→10

Refinement

Refinement on F^2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.178	w = 1/[σ^2(Fo^2) + (0.0814P)^2 + 0.3332P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
1788 reflections	Δρmax = 0.17 e Å^−3
211 parameters	Δρmin = −0.14 e Å^−3
200 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (10)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.281 (2)	0.549 (2)	0.854 (3)	0.080 (9)*	0.146 (7)
H1P	0.3013	0.5012	0.9433	0.096*	0.146 (7)
C2P	0.384 (2)	0.618 (2)	0.851 (3)	0.091 (10)*	0.146 (7)
H2P	0.4735	0.6155	0.9377	0.109*	0.146 (7)
C3P	0.356 (2)	0.690 (2)	0.722 (4)	0.076 (9)*	0.146 (7)
H3P	0.4265	0.7348	0.7208	0.091*	0.146 (7)
C4P	0.223 (3)	0.696 (3)	0.594 (4)	0.063 (10)*	0.146 (7)
H4P	0.2044	0.7450	0.5067	0.075*	0.146 (7)
C5P	−0.268 (3)	0.651 (3)	0.467 (4)	0.064 (10)*	0.146 (7)
H5P	−0.2895	0.7011	0.3813	0.077*	0.146 (7)
C6P	−0.368 (2)	0.620 (2)	0.528 (3)	0.069 (6)*	0.146 (7)
H6P	−0.4579	0.6500	0.4829	0.083*	0.146 (7)
C7P	−0.335 (2)	0.547 (2)	0.655 (4)	0.068 (6)*	0.146 (7)
H7P	−0.4036	0.5254	0.6937	0.081*	0.146 (7)
C8P	−0.202 (3)	0.503 (2)	0.725 (4)	0.059 (6)*	0.146 (7)
H8P	−0.1802	0.4563	0.8164	0.070*	0.146 (7)
C9P	0.0375 (18)	0.4713 (10)	0.695 (2)	0.070 (7)*	0.146 (7)
C10P	−0.0295 (18)	0.6192 (14)	0.4498 (18)	0.062 (8)*	0.146 (7)
C11P	−0.134 (3)	0.606 (2)	0.534 (4)	0.044 (6)*	0.146 (7)
C12P	−0.100 (2)	0.5287 (18)	0.662 (3)	0.047 (6)*	0.146 (7)
C13P	0.149 (2)	0.5524 (17)	0.724 (3)	0.050 (11)*	0.146 (7)
C14P	0.116 (2)	0.629 (2)	0.594 (3)	0.059 (11)*	0.146 (7)
C15P	−0.067 (4)	0.6981 (13)	0.302 (3)	0.052 (6)*	0.146 (7)
H15A	−0.1588	0.7304	0.2739	0.063*	0.146 (7)
H15B	0.0049	0.7510	0.3211	0.063*	0.146 (7)
C16P	0.068 (3)	0.3818 (14)	0.826 (2)	0.049 (5)*	0.146 (7)
H16A	0.1587	0.3883	0.9215	0.058*	0.146 (7)
H16B	−0.0067	0.3717	0.8676	0.058*	0.146 (7)
C1R	0.3274 (5)	0.5680 (3)	0.8296 (5)	0.0636 (12)	0.854 (7)
H1R	0.3637	0.5179	0.9155	0.076*	0.854 (7)
C2R	0.4177 (5)	0.6373 (4)	0.8030 (7)	0.0759 (14)	0.854 (7)
H2R	0.5134	0.6353	0.8733	0.091*	0.854 (7)
C3R	0.3676 (5)	0.7109 (4)	0.6718 (8)	0.0758 (14)	0.854 (7)
H3R	0.4297	0.7578	0.6544	0.091*	0.854 (7)
C4R	0.2280 (6)	0.7141 (5)	0.5695 (8)	0.0669 (16)	0.854 (7)
H4R	0.1969	0.7619	0.4795	0.080*	0.854 (7)
C5R	−0.2575 (5)	0.6257 (5)	0.4923 (8)	0.0684 (15)	0.854 (7)
H5R	−0.2952	0.6724	0.4013	0.082*	0.854 (7)
C6R	−0.3432 (5)	0.5818 (5)	0.5592 (8)	0.0860 (16)	0.854 (7)
H6R	−0.4381	0.6006	0.5174	0.103*	0.854 (7)
C7R	−0.2906 (7)	0.5074 (5)	0.6922 (8)	0.0855 (16)	0.854 (7)
H7R	−0.3514	0.4776	0.7370	0.103*	0.854 (7)
C8R	−0.1534 (6)	0.4790 (4)	0.7553 (7)	0.0702 (13)	0.854 (7)
H8R	−0.1215	0.4273	0.8391	0.084*	0.854 (7)
C9R	0.0852 (4)	0.5003 (3)	0.7581 (4)	0.0513 (11)	0.854 (7)
C10R	−0.0176 (4)	0.6507 (3)	0.4939 (5)	0.0479 (10)	0.854 (7)
C11R	−0.1105 (6)	0.6027 (4)	0.5574 (7)	0.0534 (13)	0.854 (7)
C12R	−0.0567 (6)	0.5274 (3)	0.6945 (5)	0.0511 (11)	0.854 (7)
C13R	0.1798 (6)	0.5702 (4)	0.7299 (5)	0.0489 (12)	0.854 (7)
C14R	0.1262 (5)	0.6464 (4)	0.5945 (5)	0.0477 (14)	0.854 (7)
C15R	−0.0748 (9)	0.6930 (3)	0.3131 (6)	0.0664 (16)	0.854 (7)
H15C	−0.0004	0.7317	0.2955	0.080*	0.854 (7)
H15D	−0.1505	0.7416	0.3006	0.080*	0.854 (7)
C16R	0.1321 (6)	0.3921 (3)	0.8295 (4)	0.0604 (12)	0.854 (7)
H16C	0.0983	0.3777	0.9197	0.072*	0.854 (7)
H16D	0.2345	0.3893	0.8800	0.072*	0.854 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.067 (3)	0.057 (2)	0.055 (2)	0.004 (2)	0.009 (2)	−0.0032 (18)
C2R	0.058 (3)	0.076 (3)	0.083 (3)	−0.007 (2)	0.016 (3)	−0.008 (3)
C3R	0.073 (3)	0.075 (3)	0.080 (3)	−0.016 (2)	0.030 (3)	−0.008 (3)
C4R	0.100 (4)	0.042 (2)	0.067 (3)	−0.006 (2)	0.042 (3)	0.0007 (19)
C5R	0.068 (3)	0.056 (3)	0.071 (3)	0.000 (2)	0.016 (2)	−0.019 (2)
C6R	0.057 (3)	0.090 (4)	0.102 (4)	−0.008 (3)	0.022 (3)	−0.031 (4)
C7R	0.076 (4)	0.100 (4)	0.089 (3)	−0.027 (3)	0.042 (3)	−0.021 (3)
C8R	0.084 (4)	0.069 (3)	0.063 (3)	−0.016 (3)	0.035 (3)	−0.011 (2)
C9R	0.072 (3)	0.0409 (18)	0.0337 (18)	−0.0021 (18)	0.0131 (18)	0.0009 (15)
C10R	0.070 (3)	0.0282 (17)	0.0455 (19)	0.0069 (15)	0.0230 (17)	−0.0005 (15)
C11R	0.059 (3)	0.046 (2)	0.049 (2)	0.0049 (18)	0.014 (2)	−0.0130 (17)
C12R	0.071 (3)	0.0440 (19)	0.039 (2)	−0.0111 (19)	0.022 (2)	−0.0095 (15)
C13R	0.063 (3)	0.037 (2)	0.045 (2)	−0.001 (2)	0.019 (2)	−0.0061 (15)
C14R	0.066 (3)	0.0344 (19)	0.045 (2)	0.0036 (16)	0.0244 (18)	−0.0025 (14)
C15R	0.093 (3)	0.047 (2)	0.054 (2)	0.014 (2)	0.022 (2)	0.0118 (16)
C16R	0.074 (3)	0.050 (2)	0.0444 (19)	−0.0057 (19)	0.0091 (18)	0.0102 (15)

Geometric parameters (Å, º)

C1P—C13P	1.374 (18)	C16P—C15P^i	1.484 (9)
C1P—C2P	1.387 (19)	C1R—C2R	1.364 (6)
C2P—C3P	1.367 (12)	C1R—C13R	1.419 (7)
C3P—C4P	1.369 (12)	C2R—C3R	1.391 (7)
C4P—C14P	1.390 (18)	C3R—C4R	1.356 (6)
C5P—C6P	1.375 (19)	C4R—C14R	1.438 (7)
C5P—C11P	1.392 (18)	C5R—C6R	1.342 (7)
C6P—C7P	1.368 (12)	C5R—C11R	1.423 (6)
C7P—C8P	1.378 (19)	C6R—C7R	1.409 (8)
C8P—C12P	1.393 (18)	C7R—C8R	1.349 (7)
C9P—C13P	1.494 (15)	C8R—C12R	1.427 (5)
C9P—C12P	1.518 (15)	C9R—C12R	1.388 (6)
C9P—C16P	1.536 (11)	C9R—C13R	1.409 (7)
C9P—C10P^i	1.663 (8)	C9R—C16R	1.513 (4)
C10P—C11P	1.508 (16)	C10R—C14R	1.388 (5)
C10P—C14P	1.522 (16)	C10R—C11R	1.407 (5)
C10P—C15P	1.535 (17)	C10R—C15R	1.506 (5)
C10P—C9P^i	1.663 (8)	C11R—C12R	1.440 (6)
C11P—C12P	1.406 (17)	C13R—C14R	1.439 (5)
C13P—C14P	1.417 (18)	C15R—C16R^i	1.559 (5)
C15P—C16P^i	1.484 (9)	C16R—C15R^i	1.559 (5)
C13P—C1P—C2P	119.1 (16)	C13P—C14P—C10P	114.8 (13)
C3P—C2P—C1P	121.5 (16)	C16P^i—C15P—C10P	93.7 (9)
C2P—C3P—C4P	119.9 (15)	C15P^i—C16P—C9P	92.9 (8)
C3P—C4P—C14P	120.7 (16)	C2R—C1R—C13R	121.9 (4)
C6P—C5P—C11P	120.2 (16)	C1R—C2R—C3R	120.5 (4)
C7P—C6P—C5P	119.5 (16)	C4R—C3R—C2R	119.8 (5)
C6P—C7P—C8P	121.4 (16)	C3R—C4R—C14R	122.6 (5)
C7P—C8P—C12P	120.4 (15)	C6R—C5R—C11R	121.6 (6)
C13P—C9P—C12P	106.9 (12)	C5R—C6R—C7R	120.6 (5)
C13P—C9P—C16P	118.3 (13)	C8R—C7R—C6R	120.9 (4)
C12P—C9P—C16P	114.1 (12)	C7R—C8R—C12R	120.6 (5)
C13P—C9P—C10P^i	114.7 (14)	C12R—C9R—C13R	117.8 (3)
C12P—C9P—C10P^i	115.3 (13)	C12R—C9R—C16R	120.4 (4)
C16P—C9P—C10P^i	86.9 (7)	C13R—C9R—C16R	121.1 (4)
C11P—C10P—C14P	107.0 (13)	C14R—C10R—C11R	118.0 (4)
C11P—C10P—C15P	117.2 (16)	C14R—C10R—C15R	122.3 (4)
C14P—C10P—C15P	116.7 (16)	C11R—C10R—C15R	119.3 (5)
C11P—C10P—C9P^i	115.5 (15)	C10R—C11R—C5R	122.7 (4)
C14P—C10P—C9P^i	113.4 (14)	C10R—C11R—C12R	119.6 (4)
C15P—C10P—C9P^i	86.3 (7)	C5R—C11R—C12R	117.7 (4)
C5P—C11P—C12P	120.5 (14)	C9R—C12R—C8R	121.8 (4)
C5P—C11P—C10P	122.5 (15)	C9R—C12R—C11R	119.6 (4)
C12P—C11P—C10P	115.6 (13)	C8R—C12R—C11R	118.5 (4)
C8P—C12P—C11P	117.8 (13)	C9R—C13R—C1R	122.4 (4)
C8P—C12P—C9P	127.0 (14)	C9R—C13R—C14R	119.4 (4)
C11P—C12P—C9P	114.6 (12)	C1R—C13R—C14R	118.2 (5)
C1P—C13P—C14P	120.1 (13)	C10R—C14R—C4R	123.3 (4)
C1P—C13P—C9P	124.3 (14)	C10R—C14R—C13R	119.9 (4)
C14P—C13P—C9P	115.2 (12)	C4R—C14R—C13R	116.8 (4)
C4P—C14P—C13P	118.6 (13)	C10R—C15R—C16R^i	114.2 (3)
C4P—C14P—C10P	125.9 (15)	C9R—C16R—C15R^i	111.6 (3)

Symmetry code: (i) −x, −y+1, −z+1.

(16.2P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.324 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2834 (16) Å	Cell parameters from 1000 reflections
b = 12.8132 (15) Å	θ = 3–27°
c = 8.4441 (12) Å	µ = 0.08 mm^−1
β = 112.961 (18)°	T = 299 K
V = 1024.5 (2) Å^3	Plate, orange
Z = 2	0.55 × 0.33 × 0.15 mm

Data collection

Kuma KM4CCD diffractometer	1246 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→12
5287 measured reflections	k = −15→12
1792 independent reflections	l = −10→9

Refinement

Refinement on F^2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.186	w = 1/[σ^2(Fo^2) + (0.0727P)^2 + 0.5758P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
1792 reflections	Δρmax = 0.15 e Å^−3
211 parameters	Δρmin = −0.14 e Å^−3
194 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (9)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.279 (2)	0.550 (2)	0.855 (3)	0.078 (8)*	0.162 (8)
H1P	0.3015	0.5001	0.9410	0.094*	0.162 (8)
C2P	0.379 (2)	0.623 (2)	0.856 (3)	0.084 (9)*	0.162 (8)
H2P	0.4685	0.6216	0.9444	0.101*	0.162 (8)
C3P	0.349 (2)	0.695 (2)	0.728 (3)	0.085 (9)*	0.162 (8)
H3P	0.4171	0.7441	0.7321	0.103*	0.162 (8)
C4P	0.220 (3)	0.697 (3)	0.596 (4)	0.065 (15)*	0.162 (8)
H4P	0.2019	0.7453	0.5069	0.079*	0.162 (8)
C5P	−0.268 (3)	0.651 (3)	0.471 (4)	0.065 (9)*	0.162 (8)
H5P	−0.2895	0.7025	0.3868	0.077*	0.162 (8)
C6P	−0.367 (2)	0.623 (2)	0.537 (4)	0.075 (9)*	0.162 (8)
H6P	−0.4559	0.6542	0.4954	0.090*	0.162 (8)
C7P	−0.335 (2)	0.548 (2)	0.662 (4)	0.074 (9)*	0.162 (8)
H7P	−0.4026	0.5285	0.7046	0.089*	0.162 (8)
C8P	−0.204 (3)	0.502 (2)	0.726 (4)	0.060 (6)*	0.162 (8)
H8P	−0.1824	0.4540	0.8146	0.073*	0.162 (8)
C9P	0.0356 (17)	0.4706 (10)	0.6965 (19)	0.063 (7)*	0.162 (8)
C10P	−0.0308 (17)	0.6188 (13)	0.4489 (17)	0.065 (8)*	0.162 (8)
C11P	−0.136 (2)	0.603 (2)	0.531 (3)	0.047 (9)*	0.162 (8)
C12P	−0.103 (2)	0.5272 (17)	0.660 (3)	0.047 (6)*	0.162 (8)
C13P	0.147 (2)	0.5525 (16)	0.725 (3)	0.055 (11)*	0.162 (8)
C14P	0.114 (2)	0.629 (2)	0.593 (3)	0.058 (10)*	0.162 (8)
C15P	−0.071 (4)	0.6980 (13)	0.301 (3)	0.061 (6)*	0.162 (8)
H15A	−0.1645	0.7272	0.2712	0.073*	0.162 (8)
H15B	−0.0017	0.7533	0.3219	0.073*	0.162 (8)
C16P	0.065 (3)	0.3802 (13)	0.8254 (19)	0.051 (5)*	0.162 (8)
H16A	0.1535	0.3876	0.9239	0.062*	0.162 (8)
H16B	−0.0121	0.3680	0.8626	0.062*	0.162 (8)
C1R	0.3277 (6)	0.5679 (4)	0.8297 (6)	0.0649 (13)	0.838 (8)
H1R	0.3642	0.5177	0.9151	0.078*	0.838 (8)
C2R	0.4165 (5)	0.6371 (4)	0.8038 (7)	0.0766 (15)	0.838 (8)
H2R	0.5121	0.6356	0.8744	0.092*	0.838 (8)
C3R	0.3667 (6)	0.7102 (4)	0.6731 (8)	0.0763 (14)	0.838 (8)
H3R	0.4291	0.7571	0.6562	0.092*	0.838 (8)
C4R	0.2283 (7)	0.7139 (6)	0.5701 (9)	0.067 (2)	0.838 (8)
H4R	0.1978	0.7618	0.4804	0.080*	0.838 (8)
C5R	−0.2574 (6)	0.6260 (5)	0.4913 (9)	0.0701 (17)	0.838 (8)
H5R	−0.2945	0.6722	0.3997	0.084*	0.838 (8)
C6R	−0.3447 (6)	0.5822 (6)	0.5582 (9)	0.0894 (19)	0.838 (8)
H6R	−0.4395	0.6011	0.5162	0.107*	0.838 (8)
C7R	−0.2917 (7)	0.5076 (6)	0.6923 (8)	0.0895 (19)	0.838 (8)
H7R	−0.3520	0.4778	0.7379	0.107*	0.838 (8)
C8R	−0.1541 (7)	0.4796 (5)	0.7543 (7)	0.0734 (15)	0.838 (8)
H8R	−0.1221	0.4280	0.8382	0.088*	0.838 (8)
C9R	0.0845 (5)	0.5004 (3)	0.7585 (5)	0.0527 (12)	0.838 (8)
C10R	−0.0178 (4)	0.6506 (3)	0.4937 (5)	0.0490 (11)	0.838 (8)
C11R	−0.1105 (7)	0.6031 (4)	0.5574 (8)	0.0541 (17)	0.838 (8)
C12R	−0.0572 (6)	0.5275 (3)	0.6939 (6)	0.0516 (11)	0.838 (8)
C13R	0.1796 (7)	0.5699 (4)	0.7296 (6)	0.0493 (13)	0.838 (8)
C14R	0.1268 (6)	0.6462 (4)	0.5947 (6)	0.0488 (15)	0.838 (8)
C15R	−0.0726 (9)	0.6931 (4)	0.3126 (6)	0.0684 (16)	0.838 (8)
H15C	0.0030	0.7306	0.2960	0.082*	0.838 (8)
H15D	−0.1476	0.7426	0.2990	0.082*	0.838 (8)
C16R	0.1305 (6)	0.3924 (3)	0.8300 (5)	0.0611 (13)	0.838 (8)
H16C	0.0965	0.3784	0.9202	0.073*	0.838 (8)
H16D	0.2328	0.3892	0.8805	0.073*	0.838 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.070 (3)	0.058 (3)	0.054 (3)	0.004 (3)	0.011 (2)	−0.002 (2)
C2R	0.060 (3)	0.082 (3)	0.080 (3)	−0.008 (3)	0.019 (3)	−0.009 (3)
C3R	0.073 (3)	0.078 (3)	0.080 (4)	−0.015 (3)	0.033 (3)	−0.011 (3)
C4R	0.100 (5)	0.046 (3)	0.066 (3)	−0.005 (2)	0.044 (4)	0.001 (2)
C5R	0.070 (4)	0.059 (4)	0.071 (3)	−0.001 (3)	0.017 (2)	−0.021 (3)
C6R	0.058 (3)	0.094 (5)	0.105 (5)	−0.010 (3)	0.021 (3)	−0.041 (4)
C7R	0.077 (4)	0.109 (5)	0.093 (4)	−0.034 (4)	0.044 (4)	−0.028 (4)
C8R	0.089 (4)	0.074 (3)	0.062 (3)	−0.017 (3)	0.035 (3)	−0.011 (2)
C9R	0.074 (3)	0.043 (2)	0.034 (2)	−0.003 (2)	0.014 (2)	0.0004 (16)
C10R	0.073 (3)	0.0299 (19)	0.044 (2)	0.0056 (17)	0.0225 (19)	0.0008 (17)
C11R	0.060 (3)	0.049 (3)	0.047 (3)	0.005 (2)	0.014 (2)	−0.0138 (19)
C12R	0.070 (3)	0.048 (2)	0.039 (2)	−0.012 (2)	0.023 (2)	−0.0100 (17)
C13R	0.063 (3)	0.040 (2)	0.044 (3)	0.001 (2)	0.019 (2)	−0.0062 (16)
C14R	0.068 (3)	0.035 (2)	0.045 (2)	0.0042 (19)	0.024 (2)	−0.0015 (16)
C15R	0.098 (4)	0.047 (2)	0.052 (2)	0.016 (2)	0.020 (2)	0.0137 (18)
C16R	0.075 (3)	0.051 (2)	0.044 (2)	−0.005 (2)	0.009 (2)	0.0098 (17)

Geometric parameters (Å, º)

C1P—C13P	1.376 (17)	C16P—C15P^i	1.484 (8)
C1P—C2P	1.382 (18)	C1R—C2R	1.350 (6)
C2P—C3P	1.365 (11)	C1R—C13R	1.425 (7)
C3P—C4P	1.364 (11)	C2R—C3R	1.384 (7)
C4P—C14P	1.389 (17)	C3R—C4R	1.348 (6)
C5P—C6P	1.390 (18)	C4R—C14R	1.433 (8)
C5P—C11P	1.390 (17)	C5R—C6R	1.355 (7)
C6P—C7P	1.365 (11)	C5R—C11R	1.421 (7)
C7P—C8P	1.374 (18)	C6R—C7R	1.418 (9)
C8P—C12P	1.397 (17)	C7R—C8R	1.352 (7)
C9P—C13P	1.502 (14)	C8R—C12R	1.424 (6)
C9P—C12P	1.518 (14)	C9R—C12R	1.386 (6)
C9P—C16P	1.537 (10)	C9R—C13R	1.413 (7)
C9P—C10P^i	1.665 (8)	C9R—C16R	1.510 (5)
C10P—C11P	1.511 (15)	C10R—C14R	1.397 (6)
C10P—C14P	1.518 (15)	C10R—C11R	1.403 (6)
C10P—C15P	1.536 (16)	C10R—C15R	1.510 (5)
C10P—C9P^i	1.665 (8)	C11R—C12R	1.441 (6)
C11P—C12P	1.399 (16)	C13R—C14R	1.438 (5)
C13P—C14P	1.420 (17)	C15R—C16R^i	1.563 (5)
C15P—C16P^i	1.484 (8)	C16R—C15R^i	1.563 (5)
C13P—C1P—C2P	119.6 (15)	C13P—C14P—C10P	115.4 (12)
C3P—C2P—C1P	120.8 (15)	C16P^i—C15P—C10P	93.7 (8)
C4P—C3P—C2P	120.8 (15)	C15P^i—C16P—C9P	92.9 (8)
C3P—C4P—C14P	120.4 (15)	C2R—C1R—C13R	121.8 (4)
C6P—C5P—C11P	120.2 (15)	C1R—C2R—C3R	120.6 (4)
C7P—C6P—C5P	119.9 (15)	C4R—C3R—C2R	120.5 (6)
C6P—C7P—C8P	120.4 (15)	C3R—C4R—C14R	122.1 (6)
C7P—C8P—C12P	121.2 (15)	C6R—C5R—C11R	121.8 (6)
C13P—C9P—C12P	107.1 (11)	C5R—C6R—C7R	120.1 (5)
C13P—C9P—C16P	119.2 (12)	C8R—C7R—C6R	120.5 (5)
C12P—C9P—C16P	114.4 (12)	C7R—C8R—C12R	121.3 (5)
C13P—C9P—C10P^i	113.5 (13)	C12R—C9R—C13R	117.8 (3)
C12P—C9P—C10P^i	115.0 (13)	C12R—C9R—C16R	120.3 (4)
C16P—C9P—C10P^i	86.9 (7)	C13R—C9R—C16R	121.1 (4)
C11P—C10P—C14P	107.7 (12)	C14R—C10R—C11R	118.0 (4)
C11P—C10P—C15P	116.6 (15)	C14R—C10R—C15R	121.4 (5)
C14P—C10P—C15P	117.6 (15)	C11R—C10R—C15R	120.2 (5)
C11P—C10P—C9P^i	115.2 (14)	C10R—C11R—C5R	122.5 (5)
C14P—C10P—C9P^i	112.5 (14)	C10R—C11R—C12R	119.7 (5)
C15P—C10P—C9P^i	86.2 (6)	C5R—C11R—C12R	117.9 (5)
C5P—C11P—C12P	120.0 (13)	C9R—C12R—C8R	121.8 (4)
C5P—C11P—C10P	123.1 (14)	C9R—C12R—C11R	119.8 (4)
C12P—C11P—C10P	116.5 (12)	C8R—C12R—C11R	118.4 (5)
C8P—C12P—C11P	118.2 (12)	C9R—C13R—C1R	122.6 (4)
C8P—C12P—C9P	126.6 (13)	C9R—C13R—C14R	119.5 (5)
C11P—C12P—C9P	114.7 (12)	C1R—C13R—C14R	117.9 (5)
C1P—C13P—C14P	119.9 (12)	C10R—C14R—C4R	123.3 (4)
C1P—C13P—C9P	124.6 (13)	C10R—C14R—C13R	119.6 (5)
C14P—C13P—C9P	115.0 (12)	C4R—C14R—C13R	117.0 (5)
C4P—C14P—C13P	118.5 (12)	C10R—C15R—C16R^i	114.0 (4)
C4P—C14P—C10P	125.7 (14)	C9R—C16R—C15R^i	111.6 (3)

Symmetry code: (i) −x, −y+1, −z+1.

(18.3P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2742 (15) Å	Cell parameters from 1000 reflections
b = 12.8086 (15) Å	θ = 3–27°
c = 8.4500 (12) Å	µ = 0.08 mm^−1
β = 112.999 (17)°	T = 299 K
V = 1023.6 (2) Å^3	Plate, orange
Z = 2	0.45 × 0.30 × 0.12 mm

Data collection

Kuma KM4CCD diffractometer	1032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
ω scans	h = −12→10
5405 measured reflections	k = −10→15
1776 independent reflections	l = −9→10

Refinement

Refinement on F^2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.195	w = 1/[σ^2(Fo^2) + (0.0901P)^2 + 0.3636P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1776 reflections	Δρmax = 0.18 e Å^−3
211 parameters	Δρmin = −0.15 e Å^−3
194 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (11)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.279 (2)	0.549 (2)	0.853 (3)	0.096 (12)*	0.183 (9)
H1P	0.3007	0.4982	0.9379	0.115*	0.183 (9)
C2P	0.381 (2)	0.620 (2)	0.852 (3)	0.086 (9)*	0.183 (9)
H2P	0.4713	0.6170	0.9393	0.103*	0.183 (9)
C3P	0.352 (2)	0.693 (2)	0.726 (4)	0.084 (9)*	0.183 (9)
H3P	0.4218	0.7390	0.7274	0.101*	0.183 (9)
C4P	0.219 (3)	0.699 (3)	0.598 (4)	0.068 (9)*	0.183 (9)
H4P	0.1999	0.7501	0.5128	0.081*	0.183 (9)
C5P	−0.271 (2)	0.649 (2)	0.466 (4)	0.071 (9)*	0.183 (9)
H5P	−0.2930	0.7003	0.3813	0.085*	0.183 (9)
C6P	−0.370 (2)	0.620 (2)	0.530 (3)	0.075 (6)*	0.183 (9)
H6P	−0.4588	0.6507	0.4864	0.089*	0.183 (9)
C7P	−0.338 (2)	0.546 (2)	0.657 (3)	0.070 (6)*	0.183 (9)
H7P	−0.4041	0.5292	0.7020	0.084*	0.183 (9)
C8P	−0.208 (3)	0.497 (3)	0.718 (4)	0.066 (9)*	0.183 (9)
H8P	−0.1896	0.4440	0.7992	0.080*	0.183 (9)
C9P	0.0343 (17)	0.4711 (10)	0.694 (2)	0.069 (7)*	0.183 (9)
C10P	−0.0311 (16)	0.6187 (13)	0.4492 (17)	0.063 (8)*	0.183 (9)
C11P	−0.139 (2)	0.602 (2)	0.527 (3)	0.049 (12)*	0.183 (9)
C12P	−0.1045 (19)	0.5277 (16)	0.659 (3)	0.048 (8)*	0.183 (9)
C13P	0.145 (2)	0.5547 (16)	0.725 (3)	0.046 (9)*	0.183 (9)
C14P	0.113 (2)	0.6305 (18)	0.594 (2)	0.065 (10)*	0.183 (9)
C15P	−0.069 (4)	0.6976 (12)	0.301 (3)	0.063 (6)*	0.183 (9)
H15A	−0.1617	0.7290	0.2714	0.076*	0.183 (9)
H15B	0.0020	0.7513	0.3202	0.076*	0.183 (9)
C16P	0.067 (2)	0.3826 (13)	0.8248 (19)	0.050 (5)*	0.183 (9)
H16A	0.1577	0.3907	0.9202	0.060*	0.183 (9)
H16B	−0.0072	0.3713	0.8666	0.060*	0.183 (9)
C1R	0.3272 (6)	0.5678 (4)	0.8301 (6)	0.0652 (15)	0.817 (9)
H1R	0.3634	0.5175	0.9155	0.078*	0.817 (9)
C2R	0.4176 (6)	0.6378 (4)	0.8044 (8)	0.0797 (17)	0.817 (9)
H2R	0.5132	0.6366	0.8752	0.096*	0.817 (9)
C3R	0.3668 (7)	0.7106 (5)	0.6728 (9)	0.0784 (17)	0.817 (9)
H3R	0.4288	0.7579	0.6558	0.094*	0.817 (9)
C4R	0.2278 (8)	0.7136 (6)	0.5689 (10)	0.069 (2)	0.817 (9)
H4R	0.1968	0.7609	0.4782	0.083*	0.817 (9)
C5R	−0.2564 (7)	0.6262 (6)	0.4929 (10)	0.0709 (18)	0.817 (9)
H5R	−0.2939	0.6723	0.4011	0.085*	0.817 (9)
C6R	−0.3430 (7)	0.5825 (6)	0.5606 (9)	0.0899 (19)	0.817 (9)
H6R	−0.4378	0.6017	0.5189	0.108*	0.817 (9)
C7R	−0.2912 (8)	0.5088 (6)	0.6927 (9)	0.0877 (19)	0.817 (9)
H7R	−0.3522	0.4792	0.7375	0.105*	0.817 (9)
C8R	−0.1535 (8)	0.4801 (5)	0.7560 (8)	0.0744 (16)	0.817 (9)
H8R	−0.1218	0.4290	0.8408	0.089*	0.817 (9)
C9R	0.0852 (5)	0.5003 (3)	0.7590 (5)	0.0528 (13)	0.817 (9)
C10R	−0.0173 (5)	0.6508 (3)	0.4942 (6)	0.0511 (13)	0.817 (9)
C11R	−0.1084 (8)	0.6032 (5)	0.5590 (9)	0.056 (2)	0.817 (9)
C12R	−0.0564 (7)	0.5271 (4)	0.6945 (7)	0.0517 (13)	0.817 (9)
C13R	0.1813 (7)	0.5700 (4)	0.7305 (7)	0.0534 (15)	0.817 (9)
C14R	0.1276 (6)	0.6461 (5)	0.5949 (6)	0.0501 (17)	0.817 (9)
C15R	−0.0746 (10)	0.6929 (4)	0.3126 (7)	0.0720 (18)	0.817 (9)
H15C	0.0000	0.7313	0.2949	0.086*	0.817 (9)
H15D	−0.1501	0.7418	0.3000	0.086*	0.817 (9)
C16R	0.1327 (7)	0.3922 (3)	0.8310 (5)	0.0623 (14)	0.817 (9)
H16C	0.0992	0.3778	0.9213	0.075*	0.817 (9)
H16D	0.2352	0.3895	0.8809	0.075*	0.817 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.064 (3)	0.057 (3)	0.060 (3)	0.002 (3)	0.009 (3)	−0.005 (2)
C2R	0.059 (3)	0.083 (4)	0.088 (4)	−0.007 (3)	0.019 (3)	−0.007 (3)
C3R	0.079 (4)	0.076 (4)	0.084 (4)	−0.015 (3)	0.036 (3)	−0.008 (3)
C4R	0.102 (5)	0.048 (3)	0.070 (4)	−0.005 (3)	0.048 (4)	0.002 (2)
C5R	0.078 (4)	0.062 (4)	0.064 (4)	−0.003 (3)	0.019 (3)	−0.016 (3)
C6R	0.066 (4)	0.088 (4)	0.104 (5)	0.002 (3)	0.020 (3)	−0.023 (4)
C7R	0.069 (4)	0.103 (5)	0.098 (4)	−0.019 (4)	0.040 (4)	−0.016 (4)
C8R	0.090 (5)	0.075 (4)	0.060 (4)	−0.018 (4)	0.031 (4)	−0.012 (3)
C9R	0.073 (3)	0.044 (2)	0.033 (2)	−0.004 (2)	0.012 (2)	0.0005 (19)
C10R	0.076 (3)	0.032 (2)	0.048 (3)	0.003 (2)	0.027 (2)	0.001 (2)
C11R	0.058 (3)	0.050 (3)	0.050 (3)	0.003 (2)	0.013 (3)	−0.016 (2)
C12R	0.066 (4)	0.049 (3)	0.041 (3)	−0.012 (2)	0.022 (3)	−0.008 (2)
C13R	0.063 (3)	0.044 (3)	0.053 (3)	−0.004 (3)	0.023 (3)	−0.007 (2)
C14R	0.065 (3)	0.040 (2)	0.048 (3)	0.004 (2)	0.025 (2)	−0.0023 (18)
C15R	0.102 (4)	0.050 (3)	0.059 (3)	0.016 (2)	0.026 (3)	0.014 (2)
C16R	0.069 (4)	0.056 (3)	0.050 (3)	−0.006 (2)	0.010 (2)	0.009 (2)

Geometric parameters (Å, º)

C1P—C13P	1.379 (17)	C16P—C15P^i	1.482 (8)
C1P—C2P	1.389 (19)	C1R—C2R	1.367 (8)
C2P—C3P	1.36 (2)	C1R—C13R	1.404 (8)
C3P—C4P	1.375 (19)	C2R—C3R	1.388 (8)
C4P—C14P	1.393 (17)	C3R—C4R	1.354 (7)
C5P—C6P	1.370 (18)	C4R—C14R	1.425 (8)
C5P—C11P	1.388 (17)	C5R—C6R	1.352 (5)
C6P—C7P	1.371 (18)	C5R—C11R	1.430 (8)
C7P—C8P	1.376 (19)	C6R—C7R	1.399 (8)
C8P—C12P	1.402 (17)	C7R—C8R	1.353 (9)
C9P—C13P	1.508 (15)	C8R—C12R	1.426 (6)
C9P—C12P	1.520 (15)	C9R—C12R	1.382 (7)
C9P—C16P	1.524 (16)	C9R—C13R	1.420 (7)
C9P—C10P^i	1.663 (14)	C9R—C16R	1.515 (5)
C10P—C11P	1.510 (15)	C10R—C11R	1.396 (6)
C10P—C14P	1.514 (15)	C10R—C14R	1.398 (6)
C10P—C15P	1.539 (17)	C10R—C15R	1.512 (6)
C10P—C9P^i	1.663 (14)	C11R—C12R	1.438 (7)
C11P—C12P	1.398 (17)	C13R—C14R	1.440 (6)
C13P—C14P	1.414 (17)	C15R—C16R^i	1.565 (5)
C15P—C16P^i	1.482 (8)	C16R—C15R^i	1.565 (5)
C13P—C1P—C2P	119.3 (16)	C13P—C14P—C10P	114.8 (12)
C3P—C2P—C1P	120.8 (16)	C16P^i—C15P—C10P	93.3 (9)
C2P—C3P—C4P	120.7 (16)	C15P^i—C16P—C9P	93.4 (9)
C3P—C4P—C14P	120.3 (16)	C2R—C1R—C13R	121.6 (5)
C6P—C5P—C11P	120.0 (15)	C1R—C2R—C3R	120.1 (5)
C5P—C6P—C7P	120.4 (14)	C4R—C3R—C2R	120.6 (6)
C6P—C7P—C8P	120.8 (15)	C3R—C4R—C14R	121.7 (6)
C7P—C8P—C12P	119.6 (15)	C6R—C5R—C11R	121.6 (6)
C13P—C9P—C12P	106.3 (12)	C5R—C6R—C7R	120.6 (6)
C13P—C9P—C16P	117.6 (13)	C8R—C7R—C6R	120.8 (5)
C12P—C9P—C16P	115.1 (12)	C7R—C8R—C12R	120.9 (6)
C13P—C9P—C10P^i	114.6 (13)	C12R—C9R—C13R	118.1 (4)
C12P—C9P—C10P^i	115.8 (13)	C12R—C9R—C16R	120.6 (4)
C16P—C9P—C10P^i	87.0 (7)	C13R—C9R—C16R	120.4 (4)
C11P—C10P—C14P	108.5 (12)	C11R—C10R—C14R	117.4 (5)
C11P—C10P—C15P	116.9 (15)	C11R—C10R—C15R	119.9 (6)
C14P—C10P—C15P	116.8 (15)	C14R—C10R—C15R	122.2 (5)
C11P—C10P—C9P^i	114.0 (14)	C10R—C11R—C5R	122.0 (5)
C14P—C10P—C9P^i	113.1 (11)	C10R—C11R—C12R	120.7 (6)
C15P—C10P—C9P^i	86.2 (7)	C5R—C11R—C12R	117.3 (5)
C5P—C11P—C12P	120.0 (13)	C9R—C12R—C8R	122.0 (5)
C5P—C11P—C10P	123.6 (13)	C9R—C12R—C11R	119.2 (4)
C12P—C11P—C10P	116.2 (12)	C8R—C12R—C11R	118.7 (6)
C11P—C12P—C8P	118.8 (12)	C1R—C13R—C9R	122.4 (4)
C11P—C12P—C9P	114.2 (12)	C1R—C13R—C14R	118.6 (6)
C8P—C12P—C9P	125.5 (13)	C9R—C13R—C14R	119.0 (5)
C1P—C13P—C14P	120.3 (13)	C10R—C14R—C4R	122.8 (5)
C1P—C13P—C9P	123.6 (14)	C10R—C14R—C13R	120.0 (5)
C14P—C13P—C9P	115.0 (12)	C4R—C14R—C13R	117.3 (5)
C4P—C14P—C13P	118.5 (13)	C10R—C15R—C16R^i	114.7 (4)
C4P—C14P—C10P	126.2 (14)	C9R—C16R—C15R^i	111.1 (3)

Symmetry code: (i) −x, −y+1, −z+1.

(32.4P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.319 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.264 (2) Å	Cell parameters from 1000 reflections
b = 12.8929 (19) Å	θ = 3–28°
c = 8.4043 (17) Å	µ = 0.07 mm^−1
β = 112.34 (2)°	T = 299 K
V = 1028.7 (3) Å^3	Plate, orange
Z = 2	0.34 × 0.28 × 0.12 mm

Data collection

Kuma KM4CCD diffractometer	1055 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→8
5354 measured reflections	k = −15→15
1788 independent reflections	l = −7→9

Refinement

Refinement on F^2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.076	H-atom parameters constrained
wR(F^2) = 0.243	w = 1/[σ^2(Fo^2) + (0.1311P)^2 + 0.2212P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
1788 reflections	Δρmax = 0.26 e Å^−3
211 parameters	Δρmin = −0.24 e Å^−3
128 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.070 (19)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.2781 (12)	0.5422 (13)	0.8598 (19)	0.076 (5)*	0.324 (10)
H1P	0.2979	0.4905	0.9429	0.091*	0.324 (10)
C2P	0.3799 (17)	0.6117 (17)	0.861 (2)	0.094 (7)*	0.324 (10)
H2P	0.4674	0.6097	0.9514	0.113*	0.324 (10)
C3P	0.3568 (15)	0.6836 (18)	0.734 (3)	0.092 (8)*	0.324 (10)
H3P	0.4306	0.7250	0.7326	0.110*	0.324 (10)
C4P	0.2249 (13)	0.6949 (14)	0.608 (2)	0.059 (6)*	0.324 (10)
H4P	0.2062	0.7485	0.5288	0.071*	0.324 (10)
C5P	−0.2677 (18)	0.647 (3)	0.456 (4)	0.071 (7)*	0.324 (10)
H5P	−0.2941	0.6865	0.3565	0.085*	0.324 (10)
C6P	−0.3654 (17)	0.6285 (14)	0.533 (2)	0.081 (6)*	0.324 (10)
H6P	−0.4481	0.6670	0.4998	0.098*	0.324 (10)
C7P	−0.338 (2)	0.5541 (18)	0.657 (3)	0.096 (7)*	0.324 (10)
H7P	−0.4064	0.5363	0.6996	0.115*	0.324 (10)
C8P	−0.2096 (14)	0.5056 (13)	0.718 (2)	0.056 (4)*	0.324 (10)
H8P	−0.1918	0.4545	0.8015	0.067*	0.324 (10)
C9P	0.0313 (10)	0.4711 (6)	0.6972 (12)	0.064 (4)*	0.324 (10)
C10P	−0.0225 (9)	0.6180 (8)	0.4499 (10)	0.061 (5)*	0.324 (10)
C11P	−0.1329 (15)	0.6068 (16)	0.526 (2)	0.054 (7)*	0.324 (10)
C12P	−0.1055 (16)	0.5312 (14)	0.657 (3)	0.057 (5)*	0.324 (10)
C13P	0.1440 (15)	0.5512 (13)	0.730 (2)	0.060 (6)*	0.324 (10)
C14P	0.1195 (13)	0.6251 (13)	0.6014 (18)	0.056 (7)*	0.324 (10)
C15P	−0.0427 (15)	0.6952 (7)	0.3057 (13)	0.049 (3)*	0.324 (10)
H15A	−0.1284	0.7355	0.2769	0.058*	0.324 (10)
H15B	0.0375	0.7411	0.3298	0.058*	0.324 (10)
C16P	0.0523 (15)	0.3834 (8)	0.8264 (12)	0.065 (4)*	0.324 (10)
H16A	0.1435	0.3850	0.9207	0.079*	0.324 (10)
H16B	−0.0228	0.3783	0.8693	0.079*	0.324 (10)
C1R	0.3128 (8)	0.5656 (5)	0.8368 (8)	0.0711 (19)	0.676 (10)
H1R	0.3464	0.5156	0.9226	0.085*	0.676 (10)
C2R	0.4031 (7)	0.6362 (6)	0.8160 (11)	0.085 (2)	0.676 (10)
H2R	0.4970	0.6363	0.8913	0.103*	0.676 (10)
C3R	0.3568 (8)	0.7088 (7)	0.6826 (13)	0.092 (2)	0.676 (10)
H3R	0.4201	0.7568	0.6706	0.110*	0.676 (10)
C4R	0.2209 (8)	0.7100 (7)	0.5707 (12)	0.077 (3)	0.676 (10)
H4R	0.1936	0.7555	0.4779	0.092*	0.676 (10)
C5R	−0.2640 (9)	0.6320 (11)	0.4874 (16)	0.076 (3)	0.676 (10)
H5R	−0.2960	0.6818	0.4011	0.092*	0.676 (10)
C6R	−0.3559 (8)	0.5890 (9)	0.5506 (13)	0.103 (3)	0.676 (10)
H6R	−0.4504	0.6080	0.5065	0.124*	0.676 (10)
C7R	−0.3051 (9)	0.5153 (9)	0.6841 (12)	0.107 (3)	0.676 (10)
H7R	−0.3672	0.4872	0.7291	0.128*	0.676 (10)
C8R	−0.1689 (9)	0.4841 (7)	0.7488 (11)	0.0758 (19)	0.676 (10)
H8R	−0.1395	0.4342	0.8352	0.091*	0.676 (10)
C9R	0.0696 (6)	0.4996 (4)	0.7567 (7)	0.0635 (17)	0.676 (10)
C10R	−0.0215 (5)	0.6481 (4)	0.4915 (7)	0.0567 (17)	0.676 (10)
C11R	−0.1211 (9)	0.6021 (7)	0.5506 (13)	0.060 (3)	0.676 (10)
C12R	−0.0720 (9)	0.5269 (6)	0.6858 (11)	0.061 (2)	0.676 (10)
C13R	0.1684 (9)	0.5671 (6)	0.7294 (9)	0.056 (2)	0.676 (10)
C14R	0.1194 (7)	0.6430 (7)	0.5928 (8)	0.054 (3)	0.676 (10)
C15R	−0.0798 (8)	0.6931 (4)	0.3108 (6)	0.0631 (18)	0.676 (10)
H15C	−0.0118	0.7414	0.2984	0.076*	0.676 (10)
H15D	−0.1652	0.7315	0.2947	0.076*	0.676 (10)
C16R	0.1136 (9)	0.3925 (4)	0.8322 (5)	0.0661 (18)	0.676 (10)
H16C	0.0649	0.3760	0.9079	0.079*	0.676 (10)
H16D	0.2139	0.3924	0.9006	0.079*	0.676 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.091 (5)	0.048 (4)	0.060 (4)	0.005 (4)	0.012 (4)	−0.003 (3)
C2R	0.075 (4)	0.082 (5)	0.081 (5)	−0.011 (4)	0.008 (4)	−0.002 (4)
C3R	0.098 (6)	0.081 (6)	0.088 (6)	−0.016 (4)	0.027 (4)	−0.007 (4)
C4R	0.128 (7)	0.051 (4)	0.061 (4)	−0.004 (3)	0.047 (4)	0.000 (3)
C5R	0.083 (6)	0.075 (7)	0.058 (5)	−0.007 (3)	0.012 (3)	−0.022 (4)
C6R	0.069 (5)	0.104 (8)	0.125 (8)	−0.010 (5)	0.023 (5)	−0.022 (7)
C7R	0.111 (7)	0.119 (10)	0.108 (7)	−0.053 (6)	0.060 (6)	−0.031 (6)
C8R	0.095 (5)	0.068 (4)	0.066 (4)	−0.009 (4)	0.032 (4)	−0.006 (3)
C9R	0.091 (4)	0.050 (3)	0.039 (3)	0.001 (3)	0.014 (3)	0.009 (2)
C10R	0.086 (4)	0.037 (3)	0.051 (3)	0.015 (2)	0.030 (3)	0.008 (2)
C11R	0.083 (6)	0.048 (4)	0.045 (4)	0.008 (3)	0.020 (3)	−0.009 (3)
C12R	0.099 (6)	0.047 (3)	0.043 (4)	−0.008 (3)	0.033 (4)	−0.008 (2)
C13R	0.084 (5)	0.035 (3)	0.049 (4)	0.007 (3)	0.025 (3)	0.000 (2)
C14R	0.089 (6)	0.031 (3)	0.049 (4)	0.015 (3)	0.033 (3)	0.004 (2)
C15R	0.080 (5)	0.054 (3)	0.061 (3)	0.013 (3)	0.032 (3)	0.016 (2)
C16R	0.094 (5)	0.053 (3)	0.039 (3)	−0.001 (3)	0.011 (3)	0.010 (2)

Geometric parameters (Å, º)

C1P—C2P	1.373 (15)	C16P—C15P^i	1.478 (4)
C1P—C13P	1.397 (14)	C1R—C2R	1.357 (8)
C2P—C3P	1.366 (10)	C1R—C13R	1.413 (9)
C3P—C4P	1.372 (10)	C2R—C3R	1.397 (11)
C4P—C14P	1.391 (12)	C3R—C4R	1.355 (5)
C5P—C11P	1.381 (14)	C4R—C14R	1.418 (9)
C5P—C6P	1.404 (15)	C5R—C6R	1.364 (8)
C6P—C7P	1.364 (10)	C5R—C11R	1.410 (9)
C7P—C8P	1.371 (15)	C6R—C7R	1.411 (11)
C8P—C12P	1.390 (13)	C7R—C8R	1.353 (5)
C9P—C13P	1.496 (11)	C8R—C12R	1.406 (8)
C9P—C12P	1.524 (12)	C9R—C12R	1.391 (9)
C9P—C16P	1.525 (9)	C9R—C13R	1.419 (9)
C9P—C10P^i	1.665 (7)	C9R—C16R	1.515 (5)
C10P—C11P	1.507 (8)	C10R—C14R	1.373 (6)
C10P—C15P	1.521 (8)	C10R—C11R	1.425 (6)
C10P—C14P	1.531 (8)	C10R—C15R	1.520 (5)
C10P—C9P^i	1.665 (7)	C11R—C12R	1.431 (9)
C11P—C12P	1.413 (14)	C13R—C14R	1.445 (8)
C13P—C14P	1.393 (13)	C15R—C16R^i	1.571 (3)
C15P—C16P^i	1.478 (4)	C16R—C15R^i	1.571 (3)
C2P—C1P—C13P	118.3 (11)	C13P—C14P—C10P	116.1 (9)
C3P—C2P—C1P	122.1 (12)	C16P^i—C15P—C10P	95.7 (6)
C2P—C3P—C4P	120.1 (12)	C15P^i—C16P—C9P	91.4 (6)
C3P—C4P—C14P	119.2 (10)	C2R—C1R—C13R	120.7 (6)
C11P—C5P—C6P	121.0 (13)	C1R—C2R—C3R	120.8 (6)
C7P—C6P—C5P	119.6 (13)	C4R—C3R—C2R	120.7 (8)
C6P—C7P—C8P	119.7 (13)	C3R—C4R—C14R	121.1 (8)
C7P—C8P—C12P	121.3 (11)	C6R—C5R—C11R	121.1 (9)
C13P—C9P—C12P	105.8 (10)	C5R—C6R—C7R	118.8 (7)
C13P—C9P—C16P	119.3 (8)	C8R—C7R—C6R	122.2 (6)
C12P—C9P—C16P	113.9 (8)	C7R—C8R—C12R	120.1 (7)
C13P—C9P—C10P^i	115.7 (10)	C12R—C9R—C13R	118.0 (5)
C12P—C9P—C10P^i	113.5 (10)	C12R—C9R—C16R	120.5 (6)
C16P—C9P—C10P^i	88.2 (5)	C13R—C9R—C16R	120.6 (6)
C11P—C10P—C15P	120.4 (7)	C14R—C10R—C11R	119.3 (5)
C11P—C10P—C14P	106.5 (9)	C14R—C10R—C15R	124.1 (5)
C15P—C10P—C14P	114.9 (7)	C11R—C10R—C15R	116.4 (5)
C11P—C10P—C9P^i	114.4 (11)	C5R—C11R—C10R	122.4 (7)
C15P—C10P—C9P^i	84.7 (5)	C5R—C11R—C12R	119.1 (6)
C14P—C10P—C9P^i	115.1 (10)	C10R—C11R—C12R	118.4 (6)
C5P—C11P—C12P	117.5 (10)	C9R—C12R—C8R	120.9 (6)
C5P—C11P—C10P	125.2 (10)	C9R—C12R—C11R	120.5 (5)
C12P—C11P—C10P	115.8 (10)	C8R—C12R—C11R	118.6 (7)
C8P—C12P—C11P	119.7 (10)	C1R—C13R—C9R	121.9 (5)
C8P—C12P—C9P	124.7 (10)	C1R—C13R—C14R	118.7 (7)
C11P—C12P—C9P	114.8 (9)	C9R—C13R—C14R	119.3 (6)
C14P—C13P—C1P	119.7 (10)	C10R—C14R—C4R	122.8 (6)
C14P—C13P—C9P	115.4 (10)	C10R—C14R—C13R	119.4 (6)
C1P—C13P—C9P	123.5 (10)	C4R—C14R—C13R	117.8 (6)
C4P—C14P—C13P	120.1 (8)	C10R—C15R—C16R^i	112.6 (4)
C4P—C14P—C10P	123.6 (9)	C9R—C16R—C15R^i	112.1 (4)

Symmetry code: (i) −x, −y+1, −z+1.

(38.6P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.318 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.263 (3) Å	Cell parameters from 1000 reflections
b = 12.903 (3) Å	θ = 3–28°
c = 8.397 (2) Å	µ = 0.07 mm^−1
β = 112.26 (3)°	T = 299 K
V = 1029.1 (5) Å^3	Plate, orange
Z = 2	0.34 × 0.28 × 0.12 mm

Data collection

Kuma KM4CCD diffractometer	935 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→8
5359 measured reflections	k = −15→15
1791 independent reflections	l = −7→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full with fixed elements per cycle	Secondary atom site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.289	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.176P)^2] where P = (Fo^2 + 2Fc^2)/3
1791 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.20 e Å^−3
140 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.2751 (12)	0.5450 (13)	0.8608 (18)	0.071 (5)*	0.386 (12)
H1P	0.2936	0.4943	0.9453	0.085*	0.386 (12)
C2P	0.3792 (18)	0.6140 (19)	0.864 (2)	0.103 (8)*	0.386 (12)
H2P	0.4675	0.6098	0.9523	0.124*	0.386 (12)
C3P	0.3548 (13)	0.6884 (14)	0.740 (2)	0.078 (5)*	0.386 (12)
H3P	0.4265	0.7335	0.7428	0.093*	0.386 (12)
C4P	0.2236 (13)	0.6963 (14)	0.610 (2)	0.066 (6)*	0.386 (12)
H4P	0.2042	0.7496	0.5293	0.080*	0.386 (12)
C5P	−0.2652 (17)	0.651 (2)	0.459 (3)	0.070 (6)*	0.386 (12)
H5P	−0.2880	0.6962	0.3664	0.084*	0.386 (12)
C6P	−0.365 (2)	0.629 (2)	0.529 (4)	0.114 (9)*	0.386 (12)
H6P	−0.4517	0.6624	0.4872	0.137*	0.386 (12)
C7P	−0.3376 (19)	0.5577 (16)	0.659 (3)	0.089 (6)*	0.386 (12)
H7P	−0.4039	0.5444	0.7068	0.107*	0.386 (12)
C8P	−0.2108 (14)	0.5062 (14)	0.717 (2)	0.062 (4)*	0.386 (12)
H8P	−0.1938	0.4544	0.7993	0.074*	0.386 (12)
C9P	0.0294 (10)	0.4717 (6)	0.6954 (12)	0.063 (4)*	0.386 (12)
C10P	−0.0215 (9)	0.6180 (8)	0.4500 (11)	0.065 (4)*	0.386 (12)
C11P	−0.1330 (14)	0.6065 (16)	0.524 (2)	0.055 (6)*	0.386 (12)
C12P	−0.1078 (14)	0.5313 (13)	0.653 (2)	0.054 (4)*	0.386 (12)
C13P	0.1433 (16)	0.5522 (13)	0.731 (2)	0.057 (6)*	0.386 (12)
C14P	0.1210 (11)	0.6242 (12)	0.5997 (16)	0.050 (6)*	0.386 (12)
C15P	−0.0417 (14)	0.6955 (8)	0.3054 (13)	0.057 (4)*	0.386 (12)
H15A	−0.1268	0.7363	0.2774	0.068*	0.386 (12)
H15B	0.0390	0.7406	0.3283	0.068*	0.386 (12)
C16P	0.0532 (14)	0.3836 (8)	0.8250 (12)	0.061 (4)*	0.386 (12)
H16A	0.1452	0.3857	0.9175	0.074*	0.386 (12)
H16B	−0.0203	0.3786	0.8708	0.074*	0.386 (12)
C1R	0.3092 (10)	0.5653 (6)	0.8385 (10)	0.073 (2)	0.614 (12)
H1R	0.3424	0.5155	0.9244	0.087*	0.614 (12)
C2R	0.3989 (9)	0.6377 (8)	0.8203 (15)	0.088 (3)	0.614 (12)
H2R	0.4915	0.6398	0.8990	0.105*	0.614 (12)
C3R	0.3534 (10)	0.7091 (9)	0.6845 (14)	0.100 (3)	0.614 (12)
H3R	0.4168	0.7569	0.6724	0.120*	0.614 (12)
C4R	0.2179 (10)	0.7092 (9)	0.5705 (16)	0.084 (4)	0.614 (12)
H4R	0.1917	0.7535	0.4763	0.101*	0.614 (12)
C5R	−0.2672 (10)	0.6326 (12)	0.4867 (19)	0.078 (4)	0.614 (12)
H5R	−0.2994	0.6804	0.3975	0.093*	0.614 (12)
C6R	−0.3584 (10)	0.5941 (14)	0.5549 (18)	0.101 (4)	0.614 (12)
H6R	−0.4508	0.6177	0.5168	0.122*	0.614 (12)
C7R	−0.3097 (12)	0.5181 (12)	0.6844 (16)	0.108 (4)	0.614 (12)
H7R	−0.3726	0.4900	0.7283	0.130*	0.614 (12)
C8R	−0.1745 (12)	0.4843 (9)	0.7472 (14)	0.080 (2)	0.614 (12)
H8R	−0.1466	0.4339	0.8327	0.095*	0.614 (12)
C9R	0.0652 (8)	0.4985 (5)	0.7554 (10)	0.070 (2)	0.614 (12)
C10R	−0.0259 (7)	0.6446 (6)	0.4877 (8)	0.066 (2)	0.614 (12)
C11R	−0.1253 (10)	0.6014 (10)	0.5483 (16)	0.063 (4)	0.614 (12)
C12R	−0.0761 (11)	0.5250 (7)	0.6840 (14)	0.061 (2)	0.614 (12)
C13R	0.1663 (11)	0.5654 (8)	0.7279 (13)	0.060 (3)	0.614 (12)
C14R	0.1152 (9)	0.6430 (8)	0.5922 (11)	0.065 (4)	0.614 (12)
C15R	−0.0826 (10)	0.6929 (5)	0.3085 (8)	0.064 (2)	0.614 (12)
H15C	−0.0147	0.7423	0.2990	0.077*	0.614 (12)
H15D	−0.1690	0.7300	0.2917	0.077*	0.614 (12)
C16R	0.1122 (12)	0.3916 (5)	0.8340 (7)	0.067 (2)	0.614 (12)
H16C	0.0624	0.3740	0.9081	0.080*	0.614 (12)
H16D	0.2121	0.3931	0.9039	0.080*	0.614 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1R	0.094 (6)	0.049 (5)	0.070 (5)	0.000 (5)	0.025 (5)	−0.001 (3)
C2R	0.070 (5)	0.093 (8)	0.081 (7)	−0.007 (5)	0.007 (5)	−0.013 (6)
C3R	0.118 (8)	0.101 (7)	0.078 (7)	−0.024 (5)	0.033 (5)	0.008 (5)
C4R	0.141 (10)	0.059 (6)	0.066 (6)	−0.010 (5)	0.055 (6)	−0.006 (4)
C5R	0.099 (8)	0.068 (8)	0.059 (7)	−0.007 (4)	0.022 (4)	−0.014 (4)
C6R	0.065 (6)	0.131 (14)	0.103 (10)	−0.016 (6)	0.025 (6)	−0.020 (9)
C7R	0.106 (9)	0.120 (12)	0.110 (9)	−0.042 (7)	0.053 (7)	−0.009 (8)
C8R	0.103 (6)	0.074 (6)	0.066 (5)	−0.006 (5)	0.036 (5)	−0.002 (4)
C9R	0.099 (6)	0.055 (4)	0.049 (4)	0.002 (4)	0.018 (4)	0.013 (4)
C10R	0.102 (6)	0.045 (4)	0.059 (4)	0.032 (3)	0.041 (4)	0.021 (3)
C11R	0.093 (8)	0.051 (5)	0.045 (5)	0.010 (3)	0.028 (4)	−0.004 (3)
C12R	0.094 (6)	0.046 (4)	0.049 (5)	0.004 (4)	0.033 (5)	0.002 (3)
C13R	0.082 (7)	0.042 (5)	0.060 (5)	0.007 (4)	0.031 (5)	0.000 (3)
C14R	0.110 (9)	0.031 (4)	0.063 (5)	0.019 (4)	0.044 (5)	0.006 (3)
C15R	0.085 (6)	0.049 (4)	0.070 (4)	0.016 (3)	0.043 (4)	0.016 (3)
C16R	0.092 (6)	0.055 (4)	0.046 (3)	0.005 (4)	0.018 (3)	0.013 (3)

Geometric parameters (Å, º)

C1P—C13P	1.382 (14)	C16P—C15P^i	1.468 (7)
C1P—C2P	1.383 (15)	C1R—C2R	1.360 (9)
C2P—C3P	1.371 (10)	C1R—C13R	1.407 (10)
C3P—C4P	1.379 (10)	C2R—C3R	1.401 (12)
C4P—C14P	1.384 (12)	C3R—C4R	1.357 (8)
C5P—C11P	1.380 (13)	C4R—C14R	1.421 (10)
C5P—C6P	1.392 (16)	C5R—C6R	1.362 (9)
C6P—C7P	1.366 (11)	C5R—C11R	1.407 (10)
C7P—C8P	1.376 (15)	C6R—C7R	1.408 (14)
C8P—C12P	1.390 (13)	C7R—C8R	1.356 (9)
C9P—C13P	1.507 (11)	C8R—C12R	1.408 (10)
C9P—C12P	1.525 (12)	C9R—C12R	1.386 (10)
C9P—C16P	1.528 (9)	C9R—C13R	1.434 (10)
C9P—C10P^i	1.661 (7)	C9R—C16R	1.527 (7)
C10P—C11P	1.503 (8)	C10R—C14R	1.380 (7)
C10P—C15P	1.525 (9)	C10R—C11R	1.416 (7)
C10P—C14P	1.527 (8)	C10R—C15R	1.526 (6)
C10P—C9P^i	1.661 (7)	C11R—C12R	1.445 (10)
C11P—C12P	1.405 (13)	C13R—C14R	1.457 (10)
C13P—C14P	1.392 (13)	C15R—C16R^i	1.561 (6)
C15P—C16P^i	1.468 (7)	C16R—C15R^i	1.561 (6)
C13P—C1P—C2P	119.3 (12)	C13P—C14P—C10P	115.9 (8)
C3P—C2P—C1P	121.3 (12)	C16P^i—C15P—C10P	94.9 (6)
C2P—C3P—C4P	119.8 (12)	C15P^i—C16P—C9P	92.3 (6)
C3P—C4P—C14P	119.4 (10)	C2R—C1R—C13R	120.4 (7)
C11P—C5P—C6P	121.3 (13)	C1R—C2R—C3R	120.7 (7)
C7P—C6P—C5P	120.6 (14)	C4R—C3R—C2R	120.8 (9)
C6P—C7P—C8P	119.3 (13)	C3R—C4R—C14R	121.4 (10)
C7P—C8P—C12P	120.3 (11)	C6R—C5R—C11R	121.5 (10)
C13P—C9P—C12P	106.1 (10)	C5R—C6R—C7R	118.6 (9)
C13P—C9P—C16P	118.0 (8)	C8R—C7R—C6R	122.4 (8)
C12P—C9P—C16P	115.1 (8)	C7R—C8R—C12R	120.5 (8)
C13P—C9P—C10P^i	116.4 (11)	C12R—C9R—C13R	119.0 (6)
C12P—C9P—C10P^i	113.4 (9)	C12R—C9R—C16R	121.2 (7)
C16P—C9P—C10P^i	87.4 (5)	C13R—C9R—C16R	119.0 (7)
C11P—C10P—C15P	120.0 (8)	C14R—C10R—C11R	119.4 (6)
C11P—C10P—C14P	107.8 (9)	C14R—C10R—C15R	123.4 (6)
C15P—C10P—C14P	114.9 (7)	C11R—C10R—C15R	117.2 (6)
C11P—C10P—C9P^i	113.7 (10)	C5R—C11R—C10R	122.8 (8)
C15P—C10P—C9P^i	85.3 (5)	C5R—C11R—C12R	119.2 (7)
C14P—C10P—C9P^i	114.0 (9)	C10R—C11R—C12R	117.9 (7)
C5P—C11P—C12P	117.2 (9)	C9R—C12R—C8R	121.8 (7)
C5P—C11P—C10P	125.7 (10)	C9R—C12R—C11R	120.3 (7)
C12P—C11P—C10P	116.3 (10)	C8R—C12R—C11R	117.7 (8)
C8P—C12P—C11P	120.9 (10)	C1R—C13R—C9R	122.0 (7)
C8P—C12P—C9P	124.3 (10)	C1R—C13R—C14R	119.5 (8)
C11P—C12P—C9P	114.2 (9)	C9R—C13R—C14R	118.1 (7)
C1P—C13P—C14P	119.2 (10)	C10R—C14R—C4R	124.1 (7)
C1P—C13P—C9P	124.3 (10)	C10R—C14R—C13R	119.2 (7)
C14P—C13P—C9P	114.9 (10)	C4R—C14R—C13R	116.7 (7)
C4P—C14P—C13P	120.5 (8)	C10R—C15R—C16R^i	111.2 (5)
C4P—C14P—C10P	123.6 (8)	C9R—C16R—C15R^i	111.2 (5)

Symmetry code: (i) −x, −y+1, −z+1.

(63.9P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.324 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.1383 (17) Å	Cell parameters from 1000 reflections
b = 12.9555 (13) Å	θ = 4–23°
c = 8.4110 (12) Å	µ = 0.08 mm^−1
β = 111.894 (17)°	T = 299 K
V = 1025.1 (2) Å^3	Plate, yellow
Z = 2	0.30 × 0.10 × 0.05 mm

Data collection

Kuma KM4CCD diffractometer	828 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 25.0°, θmin = 4.2°
ω scans	h = −9→12
3211 measured reflections	k = −13→15
1767 independent reflections	l = −9→4

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.115	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.391	H-atom parameters constrained
S = 1.25	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
1767 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.71 e Å^−3
160 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.2761 (10)	0.5483 (8)	0.8528 (13)	0.066 (3)	0.639 (14)
H1P	0.2966	0.4971	0.9360	0.079*	0.639 (14)
C2P	0.3780 (10)	0.6216 (10)	0.8626 (16)	0.086 (3)	0.639 (14)
H2P	0.4650	0.6205	0.9541	0.104*	0.639 (14)
C3P	0.3516 (12)	0.6958 (10)	0.7383 (19)	0.086 (3)	0.639 (14)
H3P	0.4212	0.7439	0.7440	0.103*	0.639 (14)
C4P	0.2219 (12)	0.6987 (9)	0.6055 (18)	0.068 (4)	0.639 (14)
H4P	0.2040	0.7482	0.5200	0.081*	0.639 (14)
C5P	−0.2676 (11)	0.6500 (12)	0.4717 (16)	0.065 (4)	0.639 (14)
H5P	−0.2900	0.6981	0.3835	0.078*	0.639 (14)
C6P	−0.3647 (11)	0.6286 (11)	0.5452 (17)	0.089 (3)	0.639 (14)
H6P	−0.4504	0.6644	0.5100	0.107*	0.639 (14)
C7P	−0.3361 (11)	0.5547 (11)	0.6703 (18)	0.089 (3)	0.639 (14)
H7P	−0.4024	0.5400	0.7194	0.106*	0.639 (14)
C8P	−0.2093 (12)	0.5026 (11)	0.7226 (19)	0.067 (3)	0.639 (14)
H8P	−0.1906	0.4511	0.8051	0.080*	0.639 (14)
C9P	0.0308 (7)	0.4701 (4)	0.6944 (8)	0.060 (3)*	0.639 (14)
C10P	−0.0260 (7)	0.6185 (5)	0.4514 (7)	0.061 (3)*	0.639 (14)
C11P	−0.1376 (8)	0.6016 (7)	0.5264 (12)	0.049 (4)*	0.639 (14)
C12P	−0.1086 (9)	0.5265 (6)	0.6530 (13)	0.049 (3)*	0.639 (14)
C13P	0.1448 (7)	0.5501 (6)	0.7218 (10)	0.051 (3)*	0.639 (14)
C14P	0.1165 (8)	0.6271 (7)	0.5985 (10)	0.054 (3)*	0.639 (14)
C15P	−0.0508 (14)	0.6979 (4)	0.3092 (9)	0.062 (3)	0.639 (14)
H15A	−0.1383	0.7365	0.2837	0.075*	0.639 (14)
H15B	0.0288	0.7447	0.3312	0.075*	0.639 (14)
C16P	0.0603 (14)	0.3807 (5)	0.8229 (8)	0.061 (3)	0.639 (14)
H16A	0.1537	0.3843	0.9135	0.074*	0.639 (14)
H16B	−0.0126	0.3729	0.8709	0.074*	0.639 (14)
C1R	0.3037 (12)	0.5715 (14)	0.838 (2)	0.079 (10)*	0.361 (14)
H1R	0.3382	0.5235	0.9261	0.094*	0.361 (14)
C2R	0.3945 (13)	0.6425 (17)	0.816 (3)	0.084 (5)*	0.361 (14)
H2R	0.4894	0.6434	0.8895	0.100*	0.361 (14)
C3R	0.3439 (15)	0.7150 (16)	0.680 (3)	0.096 (5)*	0.361 (14)
H3R	0.4056	0.7645	0.6674	0.116*	0.361 (14)
C4R	0.2070 (15)	0.7132 (19)	0.569 (3)	0.090 (11)*	0.361 (14)
H4R	0.1773	0.7605	0.4793	0.108*	0.361 (14)
C5R	−0.2806 (13)	0.6279 (19)	0.487 (3)	0.074 (11)*	0.361 (14)
H5R	−0.3146	0.6749	0.3970	0.089*	0.361 (14)
C6R	−0.3716 (14)	0.5879 (19)	0.556 (3)	0.092 (5)*	0.361 (14)
H6R	−0.4670	0.6068	0.5123	0.110*	0.361 (14)
C7R	−0.3202 (15)	0.517 (2)	0.694 (3)	0.101 (5)*	0.361 (14)
H7R	−0.3808	0.4934	0.7461	0.121*	0.361 (14)
C8R	−0.1841 (16)	0.483 (2)	0.751 (4)	0.076 (7)*	0.361 (14)
H8R	−0.1549	0.4330	0.8361	0.091*	0.361 (14)
C9R	0.0599 (10)	0.4982 (8)	0.7534 (17)	0.064 (5)*	0.361 (14)
C10R	−0.0382 (11)	0.6427 (11)	0.4837 (12)	0.070 (6)*	0.361 (14)
C11R	−0.1353 (10)	0.5994 (10)	0.5493 (15)	0.063 (9)*	0.361 (14)
C12R	−0.0841 (11)	0.5229 (11)	0.683 (2)	0.053 (6)*	0.361 (14)
C13R	0.1575 (10)	0.5691 (8)	0.7301 (13)	0.069 (6)*	0.361 (14)
C14R	0.1058 (11)	0.6399 (13)	0.5859 (18)	0.069 (6)*	0.361 (14)
C15R	−0.0972 (17)	0.6897 (8)	0.3050 (14)	0.060 (4)*	0.361 (14)
H15C	−0.0353	0.7452	0.2980	0.071*	0.361 (14)
H15D	−0.1903	0.7187	0.2841	0.071*	0.361 (14)
C16R	0.1094 (17)	0.3940 (9)	0.8374 (12)	0.056 (5)*	0.361 (14)
H16C	0.0514	0.3735	0.9012	0.068*	0.361 (14)
H16D	0.2073	0.3990	0.9168	0.068*	0.361 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1P	0.077 (6)	0.040 (6)	0.084 (8)	−0.001 (5)	0.033 (6)	−0.025 (5)
C2P	0.071 (5)	0.095 (7)	0.089 (7)	−0.009 (5)	0.026 (5)	−0.020 (6)
C3P	0.082 (6)	0.085 (7)	0.105 (8)	−0.029 (5)	0.052 (6)	−0.019 (7)
C4P	0.109 (10)	0.035 (6)	0.085 (8)	−0.009 (5)	0.066 (7)	−0.006 (5)
C5P	0.080 (8)	0.053 (7)	0.059 (7)	0.003 (5)	0.022 (5)	−0.003 (5)
C6P	0.072 (5)	0.088 (8)	0.108 (7)	0.008 (5)	0.035 (5)	−0.005 (6)
C7P	0.079 (5)	0.100 (8)	0.106 (7)	0.005 (5)	0.056 (5)	−0.002 (6)
C8P	0.090 (7)	0.061 (7)	0.057 (7)	0.001 (5)	0.036 (6)	0.002 (5)
C15P	0.089 (7)	0.046 (5)	0.055 (5)	0.003 (4)	0.032 (4)	0.014 (4)
C16P	0.084 (6)	0.043 (5)	0.049 (4)	−0.003 (4)	0.016 (4)	0.006 (4)

Geometric parameters (Å, º)

C1P—C13P	1.376 (9)	C16P—C15P^i	1.484 (3)
C1P—C2P	1.382 (12)	C1R—C2R	1.362 (8)
C2P—C3P	1.371 (13)	C1R—C13R	1.420 (8)
C3P—C4P	1.372 (12)	C2R—C3R	1.419 (9)
C4P—C14P	1.400 (9)	C3R—C4R	1.354 (8)
C5P—C6P	1.372 (12)	C4R—C14R	1.443 (8)
C5P—C11P	1.375 (9)	C5R—C6R	1.362 (8)
C6P—C7P	1.371 (12)	C5R—C11R	1.416 (7)
C7P—C8P	1.371 (12)	C6R—C7R	1.421 (9)
C8P—C12P	1.388 (9)	C7R—C8R	1.353 (8)
C9P—C13P	1.505 (8)	C8R—C12R	1.432 (8)
C9P—C12P	1.512 (8)	C9R—C12R	1.393 (7)
C9P—C16P	1.536 (5)	C9R—C13R	1.416 (7)
C9P—C10P^i	1.667 (3)	C9R—C16R	1.519 (5)
C10P—C11P	1.503 (8)	C10R—C14R	1.391 (7)
C10P—C14P	1.515 (8)	C10R—C11R	1.412 (7)
C10P—C15P	1.527 (5)	C10R—C15R	1.522 (5)
C10P—C9P^i	1.667 (3)	C11R—C12R	1.443 (7)
C11P—C12P	1.390 (10)	C13R—C14R	1.455 (7)
C13P—C14P	1.389 (9)	C15R—C16R^i	1.586 (4)
C15P—C16P^i	1.484 (3)	C16R—C15R^i	1.586 (4)
C13P—C1P—C2P	120.9 (9)	C4P—C14P—C10P	124.3 (8)
C3P—C2P—C1P	120.5 (8)	C16P^i—C15P—C10P	94.0 (3)
C2P—C3P—C4P	119.7 (8)	C15P^i—C16P—C9P	92.8 (3)
C3P—C4P—C14P	120.1 (10)	C2R—C1R—C13R	121.6 (7)
C6P—C5P—C11P	121.1 (10)	C1R—C2R—C3R	119.8 (7)
C7P—C6P—C5P	120.3 (9)	C4R—C3R—C2R	121.0 (7)
C8P—C7P—C6P	119.6 (8)	C3R—C4R—C14R	121.8 (7)
C7P—C8P—C12P	120.3 (9)	C6R—C5R—C11R	121.2 (7)
C13P—C9P—C12P	107.5 (5)	C5R—C6R—C7R	119.7 (7)
C13P—C9P—C16P	118.4 (6)	C8R—C7R—C6R	120.9 (7)
C12P—C9P—C16P	116.5 (6)	C7R—C8R—C12R	121.5 (7)
C13P—C9P—C10P^i	113.4 (5)	C12R—C9R—C13R	117.9 (5)
C12P—C9P—C10P^i	113.2 (5)	C12R—C9R—C16R	120.9 (7)
C16P—C9P—C10P^i	86.8 (3)	C13R—C9R—C16R	120.9 (6)
C11P—C10P—C14P	107.8 (5)	C14R—C10R—C11R	118.2 (6)
C11P—C10P—C15P	119.8 (7)	C14R—C10R—C15R	123.7 (7)
C14P—C10P—C15P	114.7 (6)	C11R—C10R—C15R	118.0 (7)
C11P—C10P—C9P^i	112.9 (5)	C10R—C11R—C5R	122.1 (6)
C14P—C10P—C9P^i	114.1 (6)	C10R—C11R—C12R	118.5 (6)
C15P—C10P—C9P^i	86.3 (3)	C5R—C11R—C12R	119.4 (6)
C5P—C11P—C12P	118.6 (8)	C9R—C12R—C8R	122.3 (7)
C5P—C11P—C10P	124.8 (8)	C9R—C12R—C11R	120.3 (6)
C12P—C11P—C10P	116.5 (6)	C8R—C12R—C11R	117.1 (6)
C8P—C12P—C11P	120.0 (7)	C9R—C13R—C1R	122.8 (6)
C8P—C12P—C9P	124.5 (7)	C9R—C13R—C14R	118.1 (6)
C11P—C12P—C9P	115.3 (5)	C1R—C13R—C14R	119.0 (6)
C1P—C13P—C14P	118.6 (7)	C10R—C14R—C4R	122.9 (7)
C1P—C13P—C9P	124.7 (7)	C10R—C14R—C13R	120.0 (6)
C14P—C13P—C9P	116.5 (5)	C4R—C14R—C13R	116.7 (6)
C13P—C14P—C4P	120.1 (8)	C10R—C15R—C16R^i	111.3 (6)
C13P—C14P—C10P	115.2 (6)	C9R—C16R—C15R^i	109.7 (5)

Symmetry code: (i) −x, −y+1, −z+1.

(84.6P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.330 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.961 (5) Å	Cell parameters from 1000 reflections
b = 12.976 (4) Å	θ = 3–28°
c = 8.504 (2) Å	µ = 0.08 mm^−1
β = 111.86 (4)°	T = 299 K
V = 1020.1 (6) Å^3	Plate, pale yellow
Z = 2	0.32 × 0.22 × 0.10 mm

Data collection

Kuma KM4CCD diffractometer	835 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.105
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ω scans	h = −11→11
5328 measured reflections	k = −15→14
1794 independent reflections	l = −8→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full with fixed elements per cycle	Secondary atom site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.121	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.368	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
1794 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.34 e Å^−3
178 restraints	Δρmin = −0.39 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1P	0.2819 (8)	0.5568 (5)	0.8480 (8)	0.075 (2)	0.846 (10)
H1P	0.3081	0.5066	0.9321	0.089*	0.846 (10)
C2P	0.3777 (8)	0.6366 (6)	0.8526 (10)	0.090 (2)	0.846 (10)
H2P	0.4672	0.6402	0.9414	0.108*	0.846 (10)
C3P	0.3408 (9)	0.7088 (6)	0.7283 (11)	0.097 (3)	0.846 (10)
H3P	0.4057	0.7613	0.7323	0.116*	0.846 (10)
C4P	0.2090 (8)	0.7054 (4)	0.5968 (9)	0.0728 (19)	0.846 (10)
H4P	0.1865	0.7547	0.5114	0.087*	0.846 (10)
C5P	−0.2830 (8)	0.6417 (5)	0.4830 (8)	0.0713 (19)	0.846 (10)
H5P	−0.3116	0.6897	0.3955	0.086*	0.846 (10)
C6P	−0.3756 (8)	0.6171 (7)	0.5630 (10)	0.092 (2)	0.846 (10)
H6P	−0.4643	0.6505	0.5323	0.111*	0.846 (10)
C7P	−0.3389 (9)	0.5443 (7)	0.6865 (11)	0.096 (3)	0.846 (10)
H7P	−0.4028	0.5272	0.7390	0.115*	0.846 (10)
C8P	−0.2050 (8)	0.4955 (5)	0.7343 (8)	0.072 (2)	0.846 (10)
H8P	−0.1795	0.4457	0.8192	0.086*	0.846 (10)
C9P	0.0380 (6)	0.4696 (4)	0.6941 (6)	0.0595 (17)*	0.846 (10)
C10P	−0.0387 (6)	0.6183 (4)	0.4508 (6)	0.0597 (17)*	0.846 (10)
C11P	−0.1488 (7)	0.5968 (4)	0.5297 (6)	0.0519 (15)*	0.846 (10)
C12P	−0.1095 (6)	0.5205 (4)	0.6561 (7)	0.0547 (16)*	0.846 (10)
C13P	0.1470 (7)	0.5533 (4)	0.7165 (7)	0.0569 (16)*	0.846 (10)
C14P	0.1083 (7)	0.6292 (4)	0.5894 (7)	0.0545 (16)*	0.846 (10)
C15P	−0.0806 (9)	0.6966 (4)	0.3063 (7)	0.070 (2)	0.846 (10)
H15A	−0.1760	0.7259	0.2813	0.085*	0.846 (10)
H15B	−0.0095	0.7509	0.3247	0.085*	0.846 (10)
C16P	0.0772 (10)	0.3798 (4)	0.8213 (7)	0.077 (2)	0.846 (10)
H16A	0.1703	0.3886	0.9128	0.092*	0.846 (10)
H16B	0.0028	0.3655	0.8663	0.092*	0.846 (10)
C1R	0.342 (2)	0.563 (2)	0.857 (3)	0.071 (9)*	0.154 (10)
H1R	0.3703	0.5162	0.9454	0.086*	0.154 (10)
C2R	0.442 (3)	0.629 (3)	0.841 (4)	0.102 (10)*	0.154 (10)
H2R	0.5369	0.6256	0.9180	0.122*	0.154 (10)
C3R	0.406 (3)	0.703 (3)	0.710 (4)	0.123 (10)*	0.154 (10)
H3R	0.4756	0.7478	0.7015	0.147*	0.154 (10)
C4R	0.267 (3)	0.709 (2)	0.597 (4)	0.083 (10)*	0.154 (10)
H4R	0.2423	0.7589	0.5130	0.100*	0.154 (10)
C5R	−0.240 (2)	0.639 (2)	0.475 (4)	0.072 (9)*	0.154 (10)
H5R	−0.2668	0.6874	0.3882	0.087*	0.154 (10)
C6R	−0.343 (3)	0.602 (3)	0.530 (5)	0.107 (10)*	0.154 (10)
H6R	−0.4378	0.6255	0.4799	0.129*	0.154 (10)
C7R	−0.305 (3)	0.529 (3)	0.663 (5)	0.117 (11)*	0.154 (10)
H7R	−0.3749	0.5030	0.7007	0.141*	0.154 (10)
C8R	−0.166 (3)	0.497 (3)	0.736 (5)	0.090 (10)*	0.154 (10)
H8R	−0.1411	0.4524	0.8283	0.108*	0.154 (10)
C9R	0.089 (2)	0.4984 (13)	0.754 (3)	0.068 (9)*	0.154 (10)
C10R	0.014 (2)	0.6423 (16)	0.4918 (19)	0.047 (7)*	0.154 (10)
C11R	−0.095 (2)	0.6071 (13)	0.5437 (19)	0.035 (6)*	0.154 (10)
C12R	−0.056 (2)	0.5266 (15)	0.677 (3)	0.039 (6)*	0.154 (10)
C13R	0.196 (2)	0.5642 (12)	0.743 (2)	0.045 (9)*	0.154 (10)
C14R	0.158 (2)	0.6383 (17)	0.604 (2)	0.046 (9)*	0.154 (10)
C15R	−0.029 (4)	0.6900 (15)	0.314 (2)	0.065 (6)*	0.154 (10)
H15C	0.0574	0.7084	0.2940	0.078*	0.154 (10)
H15D	−0.0844	0.7524	0.3085	0.078*	0.154 (10)
C16R	0.124 (3)	0.3891 (14)	0.828 (2)	0.070 (6)*	0.154 (10)
H16C	0.0994	0.3831	0.9282	0.085*	0.154 (10)
H16D	0.2257	0.3745	0.8599	0.085*	0.154 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1P	0.065 (4)	0.075 (4)	0.068 (4)	0.008 (3)	0.007 (3)	−0.020 (3)
C2P	0.067 (5)	0.101 (6)	0.095 (5)	−0.001 (4)	0.024 (4)	−0.040 (5)
C3P	0.089 (6)	0.098 (6)	0.123 (6)	−0.030 (4)	0.062 (5)	−0.045 (5)
C4P	0.090 (5)	0.054 (4)	0.088 (4)	−0.020 (4)	0.049 (4)	−0.021 (3)
C5P	0.085 (5)	0.070 (4)	0.060 (4)	0.005 (4)	0.028 (4)	−0.014 (3)
C6P	0.072 (4)	0.114 (6)	0.093 (6)	0.007 (4)	0.033 (4)	−0.027 (5)
C7P	0.088 (5)	0.110 (6)	0.112 (6)	−0.016 (5)	0.062 (5)	−0.044 (5)
C8P	0.110 (5)	0.063 (4)	0.059 (4)	−0.015 (4)	0.051 (4)	−0.013 (3)
C15P	0.104 (5)	0.050 (3)	0.058 (3)	0.015 (3)	0.032 (3)	0.015 (3)
C16P	0.114 (6)	0.056 (3)	0.053 (3)	0.006 (3)	0.023 (3)	0.011 (3)

Geometric parameters (Å, º)

C1P—C13P	1.393 (8)	C16P—C15P^i	1.480 (5)
C1P—C2P	1.398 (9)	C1R—C2R	1.357 (10)
C2P—C3P	1.357 (9)	C1R—C13R	1.414 (15)
C3P—C4P	1.373 (9)	C2R—C3R	1.409 (16)
C4P—C14P	1.393 (8)	C3R—C4R	1.359 (10)
C5P—C6P	1.372 (9)	C4R—C14R	1.439 (14)
C5P—C11P	1.375 (8)	C5R—C6R	1.358 (10)
C6P—C7P	1.357 (9)	C5R—C11R	1.406 (14)
C7P—C8P	1.394 (9)	C6R—C7R	1.425 (16)
C8P—C12P	1.387 (8)	C7R—C8R	1.357 (10)
C9P—C13P	1.496 (7)	C8R—C12R	1.410 (15)
C9P—C12P	1.531 (7)	C9R—C13R	1.395 (13)
C9P—C16P	1.539 (6)	C9R—C12R	1.400 (13)
C9P—C10P^i	1.682 (5)	C9R—C16R	1.538 (9)
C10P—C14P	1.506 (7)	C10R—C11R	1.390 (12)
C10P—C11P	1.509 (7)	C10R—C14R	1.392 (12)
C10P—C15P	1.528 (6)	C10R—C15R	1.536 (9)
C10P—C9P^i	1.682 (5)	C11R—C12R	1.483 (14)
C11P—C12P	1.405 (6)	C13R—C14R	1.462 (14)
C13P—C14P	1.407 (7)	C15R—C16R^i	1.600 (7)
C15P—C16P^i	1.480 (5)	C16R—C15R^i	1.600 (7)
C13P—C1P—C2P	119.5 (6)	C13P—C14P—C10P	116.4 (5)
C3P—C2P—C1P	120.4 (6)	C16P^i—C15P—C10P	94.1 (4)
C2P—C3P—C4P	120.8 (6)	C15P^i—C16P—C9P	93.5 (4)
C3P—C4P—C14P	120.9 (6)	C2R—C1R—C13R	122.2 (14)
C6P—C5P—C11P	121.3 (6)	C1R—C2R—C3R	121.6 (14)
C7P—C6P—C5P	120.6 (6)	C4R—C3R—C2R	119.3 (13)
C6P—C7P—C8P	119.6 (6)	C3R—C4R—C14R	121.6 (14)
C12P—C8P—C7P	120.4 (6)	C6R—C5R—C11R	123.2 (14)
C13P—C9P—C12P	107.9 (4)	C5R—C6R—C7R	119.8 (14)
C13P—C9P—C16P	118.6 (5)	C8R—C7R—C6R	119.5 (14)
C12P—C9P—C16P	116.6 (5)	C7R—C8R—C12R	123.2 (14)
C13P—C9P—C10P^i	112.6 (4)	C13R—C9R—C12R	119.6 (10)
C12P—C9P—C10P^i	113.8 (4)	C13R—C9R—C16R	122.2 (13)
C16P—C9P—C10P^i	86.1 (3)	C12R—C9R—C16R	117.8 (10)
C14P—C10P—C11P	109.0 (4)	C11R—C10R—C14R	119.6 (10)
C14P—C10P—C15P	117.5 (5)	C11R—C10R—C15R	118.5 (12)
C11P—C10P—C15P	117.0 (5)	C14R—C10R—C15R	121.8 (12)
C14P—C10P—C9P^i	111.7 (4)	C10R—C11R—C5R	125.1 (11)
C11P—C10P—C9P^i	113.7 (4)	C10R—C11R—C12R	117.7 (10)
C15P—C10P—C9P^i	86.4 (3)	C5R—C11R—C12R	117.1 (11)
C5P—C11P—C12P	118.9 (5)	C9R—C12R—C8R	124.4 (13)
C5P—C11P—C10P	125.6 (5)	C9R—C12R—C11R	117.9 (10)
C12P—C11P—C10P	115.4 (4)	C8R—C12R—C11R	116.9 (11)
C8P—C12P—C11P	119.1 (5)	C9R—C13R—C1R	124.5 (12)
C8P—C12P—C9P	125.0 (5)	C9R—C13R—C14R	118.6 (11)
C11P—C12P—C9P	115.9 (4)	C1R—C13R—C14R	116.9 (11)
C1P—C13P—C14P	120.0 (5)	C10R—C14R—C4R	123.3 (11)
C1P—C13P—C9P	124.3 (5)	C10R—C14R—C13R	118.2 (11)
C14P—C13P—C9P	115.6 (5)	C4R—C14R—C13R	118.3 (11)
C4P—C14P—C13P	118.4 (6)	C10R—C15R—C16R^i	110.9 (7)
C4P—C14P—C10P	125.2 (5)	C9R—C16R—C15R^i	107.6 (7)

Symmetry code: (i) −x, −y+1, −z+1.

(100P)

Crystal data

C32H24	F(000) = 432
Mr = 408.51	Dx = 1.339 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8457 (13) Å	Cell parameters from 1000 reflections
b = 12.9974 (13) Å	θ = 4–24°
c = 8.5319 (11) Å	µ = 0.08 mm^−1
β = 111.891 (15)°	T = 299 K
V = 1013.1 (2) Å^3	Plate, colourless
Z = 2	0.30 × 0.10 × 0.05 mm

Data collection

Kuma KM4CCD diffractometer	1028 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 25.0°, θmin = 4.1°
ω scans	h = −8→11
3193 measured reflections	k = −13→15
1764 independent reflections	l = −10→4

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1084P)^2] where P = (Fo^2 + 2Fc^2)/3
1764 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1P	0.2851 (3)	0.5578 (2)	0.8475 (4)	0.0612 (9)
H1P	0.3115	0.5077	0.9313	0.073*
C2P	0.3808 (3)	0.6374 (3)	0.8558 (5)	0.0793 (12)
H2P	0.4705	0.6412	0.9456	0.095*
C3P	0.3431 (4)	0.7108 (3)	0.7312 (6)	0.0814 (12)
H3P	0.4073	0.7644	0.7368	0.098*
C4P	0.2119 (3)	0.7054 (2)	0.5994 (4)	0.0596 (8)
H4P	0.1886	0.7548	0.5146	0.071*
C5P	−0.2809 (3)	0.6425 (2)	0.4848 (3)	0.0537 (8)
H5P	−0.3080	0.6920	0.4001	0.064*
C6P	−0.3756 (3)	0.6177 (3)	0.5638 (4)	0.0691 (10)
H6P	−0.4661	0.6502	0.5322	0.083*
C7P	−0.3366 (4)	0.5455 (3)	0.6880 (5)	0.0699 (10)
H7P	−0.4000	0.5294	0.7423	0.084*
C8P	−0.2029 (3)	0.4957 (2)	0.7344 (4)	0.0558 (8)
H8P	−0.1774	0.4463	0.8193	0.067*
C9P	0.0396 (3)	0.46822 (19)	0.6942 (3)	0.0390 (6)
C10P	−0.0363 (3)	0.61748 (17)	0.4503 (3)	0.0387 (6)
C11P	−0.1459 (3)	0.59486 (18)	0.5296 (3)	0.0382 (6)
C12P	−0.1075 (3)	0.51904 (18)	0.6554 (3)	0.0386 (6)
C13P	0.1505 (3)	0.55211 (19)	0.7159 (3)	0.0409 (7)
C14P	0.1121 (3)	0.62769 (18)	0.5892 (3)	0.0401 (7)
C15P	−0.0781 (4)	0.6976 (2)	0.3075 (3)	0.0630 (9)
H15A	−0.1726	0.7292	0.2860	0.076*
H15B	−0.0037	0.7499	0.3246	0.076*
C16P	0.0816 (4)	0.3788 (2)	0.8215 (4)	0.0654 (9)
H16A	0.1780	0.3867	0.9092	0.078*
H16B	0.0092	0.3657	0.8710	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1P	0.0497 (17)	0.065 (2)	0.0584 (19)	0.0133 (15)	0.0080 (14)	−0.0230 (16)
C2P	0.0394 (17)	0.100 (3)	0.092 (3)	−0.0058 (19)	0.0165 (17)	−0.050 (2)
C3P	0.057 (2)	0.092 (3)	0.108 (3)	−0.0289 (19)	0.046 (2)	−0.052 (3)
C4P	0.068 (2)	0.0520 (17)	0.075 (2)	−0.0167 (15)	0.0464 (18)	−0.0203 (15)
C5P	0.0454 (16)	0.0632 (19)	0.0481 (17)	0.0096 (13)	0.0125 (13)	−0.0131 (14)
C6P	0.0427 (17)	0.093 (3)	0.070 (2)	0.0041 (17)	0.0186 (16)	−0.029 (2)
C7P	0.0553 (19)	0.088 (2)	0.083 (2)	−0.0172 (18)	0.0455 (17)	−0.034 (2)
C8P	0.0711 (19)	0.0543 (18)	0.0564 (18)	−0.0122 (14)	0.0404 (15)	−0.0087 (14)
C9P	0.0527 (15)	0.0342 (14)	0.0302 (13)	0.0061 (11)	0.0157 (11)	0.0027 (10)
C10P	0.0512 (15)	0.0287 (13)	0.0380 (15)	0.0055 (11)	0.0185 (12)	0.0021 (11)
C11P	0.0419 (14)	0.0386 (14)	0.0341 (14)	0.0026 (11)	0.0143 (11)	−0.0081 (11)
C12P	0.0484 (15)	0.0340 (14)	0.0377 (14)	−0.0044 (11)	0.0211 (11)	−0.0091 (11)
C13P	0.0418 (14)	0.0394 (14)	0.0403 (14)	0.0074 (11)	0.0140 (11)	−0.0086 (12)
C14P	0.0425 (14)	0.0384 (14)	0.0463 (16)	−0.0035 (11)	0.0246 (12)	−0.0138 (12)
C15P	0.098 (2)	0.0460 (17)	0.0482 (18)	0.0135 (16)	0.0314 (17)	0.0125 (14)
C16P	0.104 (2)	0.0458 (17)	0.0449 (18)	0.0137 (16)	0.0255 (16)	0.0103 (14)

Geometric parameters (Å, º)

C1P—C2P	1.383 (5)	C9P—C12P	1.512 (3)
C1P—C13P	1.383 (4)	C9P—C16P	1.539 (4)
C2P—C3P	1.372 (5)	C9P—C10P^i	1.652 (3)
C3P—C4P	1.362 (5)	C10P—C11P	1.501 (3)
C4P—C14P	1.389 (4)	C10P—C14P	1.505 (3)
C5P—C6P	1.377 (4)	C10P—C15P	1.537 (3)
C5P—C11P	1.384 (4)	C10P—C9P^i	1.652 (3)
C6P—C7P	1.359 (5)	C11P—C12P	1.401 (3)
C7P—C8P	1.385 (4)	C13P—C14P	1.404 (4)
C8P—C12P	1.379 (3)	C15P—C16P^i	1.473 (4)
C9P—C13P	1.505 (3)	C16P—C15P^i	1.473 (4)
C2P—C1P—C13P	120.7 (3)	C11P—C10P—C9P^i	112.74 (19)
C3P—C2P—C1P	119.8 (3)	C14P—C10P—C9P^i	112.97 (18)
C4P—C3P—C2P	120.2 (3)	C15P—C10P—C9P^i	86.59 (17)
C3P—C4P—C14P	121.3 (3)	C5P—C11P—C12P	118.8 (2)
C6P—C5P—C11P	121.1 (3)	C5P—C11P—C10P	124.5 (2)
C7P—C6P—C5P	119.8 (3)	C12P—C11P—C10P	116.7 (2)
C6P—C7P—C8P	120.5 (3)	C8P—C12P—C11P	119.4 (2)
C12P—C8P—C7P	120.4 (3)	C8P—C12P—C9P	124.7 (2)
C13P—C9P—C12P	107.61 (19)	C11P—C12P—C9P	115.9 (2)
C13P—C9P—C16P	118.0 (2)	C1P—C13P—C14P	119.3 (2)
C12P—C9P—C16P	117.9 (2)	C1P—C13P—C9P	124.8 (2)
C13P—C9P—C10P^i	113.05 (19)	C14P—C13P—C9P	115.9 (2)
C12P—C9P—C10P^i	112.35 (18)	C4P—C14P—C13P	118.7 (2)
C16P—C9P—C10P^i	86.71 (19)	C4P—C14P—C10P	124.7 (2)
C11P—C10P—C14P	108.19 (19)	C13P—C14P—C10P	116.6 (2)
C11P—C10P—C15P	117.7 (2)	C16P^i—C15P—C10P	93.5 (2)
C14P—C10P—C15P	117.3 (2)	C15P^i—C16P—C9P	93.2 (2)

Symmetry code: (i) −x, −y+1, −z+1.