1,1-Di(9-fluorenyl)­ethanol, a ­by-­product from the acetyl­ation of 9-fluorenyl­lithium

Treatment of 9-fluorenyl­lithium with acetyl chloride produces 9-acetyl­fluorene, (I), and several by-products. Among them is a compound unequivocally identified for the first time as the addition product of (I) with 9-fluorenyl­lithium, 1,1-di(9-fluorenyl)­ethanol, C₂₈H₂₂O, (II). The two fluorene-ring planes of (II) are essentially perpendicular [89.90 (9)°]. A number of intermolecular non-bonding distances are well within or close to the sum of their respective van der Waals radii and may be responsible for the rarely observed large bowing of one of the fluorene rings. This bowing apparently arises from two mol­ecules impinging on the convex face of the bowed ring, augmented by hydrogen bonding between the peripheral [pi] electrons of the concave face and the hydroxyl H atom of another mol­ecule adjacent to that face.

S1. Comment

The reaction of 9-fluorenyllithium with acetyl chloride provided 9-acetylfluorene, (I), as the major product (Meyers et al., 2000) along with byproducts, among which was the `diacetylfluorene', unequivocally identified as 9-(1-acetoxyethylidene)fluorene (Robinson et al., 2000). A second byproduct has now been isolated and characterized unequivocally as 1,1-bis(9-fluorenyl)ethanol, (II). As shown in the Scheme, we believe that (II) results from an aldol addition of 9-fluorenyllithium to (I). Although the acetylation of 9-fluorenyl anion has been reported by several investigators, (2) was neither identified nor suggested as a byproduct (cf. Naik et al., 1988; Rouzaud et al., 1965; Scherf & Brown, 1961; Greenhow et al., 1953; Von & Wagner, 1944; and Miller & Bachman, 1935), nor has it been noted in any other previous literature. \sch

The X-ray structure of (II) with atom numbering is shown in Fig. 1. The two fluorenyl-ring planes are nearly perpendicular to each other, subtending an angle of 89.90 (9)°. Some of the 18 short intramolecular contacts involving H atoms are as much as 0.36 Å less than the sum of their respective van der Waals radii [contact radii used for C, H, and O are 1.70, 1.20, and 1.52 Å, respectively (Bondi, 1964)]. However, little angular distortion is exhibited other than that possibly suggested by the differences in angles subtended from the common sp³– hybridized C10 atom, which range from 105.7 (2) to 112.1 (2)°. A surprising feature exhibited by (II) is the significant bowing of one of its fluorene-ring planes, illustrated by the labeled central molecule of Fig. 2 and substantiated by the out-of-plane distances of the C atoms of the normally planar fluorene ring, e.g. C2' -0.192 (4), C7' -0.168 (4), C9' 0.200 Å (3), etc. A full list of the fluorene least-squares plane parameters can be found in the CIF. No similar bowing is exhibited in the X-ray structures of the many other fluorene compounds we have reported.

Fig. 2 also shows the three surrounding molecules which impinge on both faces of the central, bowed, fluorene ring, and the resulting seven short intermolecular interactions. Of these, three are less than or equal to the sum of their respective van der Waals radii, and four are very slightly longer (> 0.0 but < 0.10 Å). In our opinion, the three which involve direct impingement on the atoms toward the ends of the convex face of the origin molecule are mainly responsible for the observed bowing. These interactions, respectively, are 0.09 Å less than, equal to, and 0.02 Å greater than the sum of their van der Walls radii. In addition, there is a possible weak hydrogen bond from the hydroxyl group of molecule 3 (symmetry operator: x, -y, 1/2 + z) to the pi cloud of the origin molecule's upper phenyl ring (see Fig. 2). Using the centroid (Cg1) of this phenyl ring as the acceptor site, the hydrogen-bond geometry (O1—H1···Cg1) is D—H 0.93, H···Cg1 3.02 Å, D···Cg1 3.528 (2) Å and D—H—Cg1 123°. It should be noted that the H···Cg1 distance is longer than that between this H atom and the closest C atoms of the origin molecule's upper phenyl ring, viz. C1' 2.71, and C2' 2.96 Å. Thus, the suspected hydrogen bond may not be directed at the phenyl- ring centroid per se, but more toward its periphery, producing a minor attractive force which may contribute to the observed bowing. That this bowing of one of the fluorene rings is a solid-state phenomenon is supported by the molecular symmetry of (II) in solution indicated by the NMR equivalency of the corresponding atoms of its two fluorene moieties.

Related literature

For related literature, see: Bondi (1964); Greenhow et al. (1953); Meyers et al. (2000); Miller & Bachman (1935); Naik et al. (1988); Robinson et al. (2000); Rouzaud et al. (1965); Scherf & Brown (1961, 1961); Sheldrick (1997); Von & Wagner (1944).

S2. Experimental

Compound (II) was isolated by flash chromatography as one of the byproducts in our preparation of (I) from the reaction of 9-fluorenyllithium with acetyl chloride in THF under argon (Meyers et al., 2000; Robinson et al., 2000). Recrystallization from hexane provided colorless crystals, m.p. 454–455.5 K (corr. no decomp.), used for the NMR and X-ray diffraction studies. NMR (Varian VXR 300; 300 MHz ¹H, 75 MHz ¹³C; CDCl₃), ¹H: δ 1.01 (s, 3H), 1.40 (s, 1H), 4.78 (s, 2H), 7.27 (m, 4H, J = 1.2, 2.7, 7.5 Hz), 7.42 (m, 4H, J = 7.2 Hz), 7.68 (d, 2H, J = 7.5 Hz), 7.83 (m, 6H, J = 7.2 Hz). ¹³C: δ 22.34, 56.29, 77.17, 119.82, 120.03, 126.61, 126.65, 126.79, 127.40, 127.67, 142.45, 142.73, 143.59, 144.18.

S3. Refinement

The rotational orientations of the methyl and hydroxyl groups were refined by the circular Fourier methods available in SHELXL97 (Sheldrick, 1997). All H atoms are riding.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON (Spek, 2000).

Figures

	Fig. 1. The molecular structure and atom-numbering scheme for (II) with displacement ellipsoids at the 30% probablilty level.
	Fig. 2. A space-filling representation of the origin molecule surrounded by the three equivalent molecules which impinge upon it. The hydroxyl O atoms are shaded grey. Note the bowing of the origin molecule. (Symmetry Operators: Molecule 1: -x, 1/2 + y, 1 1/2 - z; Molecule 2: x, -y, 1/2 + z; Molecule 3: x, -y, -1/2 + z.)

1,1-Di-9-fluorenylethanol

Crystal data

C28H22O	Dx = 1.244 Mg m^−3
Mr = 374.46	Melting point = 454–455.5 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
a = 34.792 (5) Å	Cell parameters from 25 reflections
b = 10.0951 (17) Å	θ = 7.6–10.8°
c = 11.6821 (17) Å	µ = 0.07 mm^−1
β = 102.962 (12)°	T = 296 K
V = 3998.5 (10) Å^3	Plate, colorless
Z = 8	0.36 × 0.31 × 0.05 mm
F(000) = 1584

Data collection

Rigaku AFC-5S diffractometer	Rint = 0.012
Radiation source: sealed tube	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = 0→41
ω (rate 1° min^–1) scans	k = 0→12
3580 measured reflections	l = −13→13
3521 independent reflections	3 standard reflections every 150 reflections
1330 reflections with I > 2σ(I)	intensity decay: 0.9%

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)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0542P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
3521 reflections	Δρmax = 0.11 e Å^−3
265 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Special details

Geometry. SELECTED LEAST SQUARES PLANES

Definitions: Sigref - R·M·S-Error of the Contributing Atoms Sigpln - Sqrt(Sum(j=1:N)(D(j)**2/(N-3)) Chisq - Chi-Squared = Sum(j=1:N)(D(j)**2)/Sigref**2

——-Plane 1———-

Atoms Distance From Defining Plane with s.u. Plane

C1 - 0.019 (4) C2 - 0.076 (4) C3 - 0.049 (5) C4 0.013 (5) C4a 0.048 (3) C4b 0.044 (4) C5 0.027 (5) C6 - 0.022 (6) C7 - 0.076 (4) C8 - 0.052 (4) C8a 0.033 (4) C9 0.082 (3) C9a 0.047 (3)

Sigref 0.004 Sigpln 0.056 Chisq 1969.2 ===========================

——-Plane 2———-

Atoms Distance From Defining Plane with s.u. Plane

C1' -0.085 (3) C2' -0.192 (4) C3' -0.103 (4) C4' 0.060 (3) C4a' 0.132 (3) C4b' 0.120 (3) C5' 0.030 (4) C6' -0.115 (5) C7' -0.168 (4) C8' -0.067 (3) C8a' 0.088 (3) C9' 0.200 (3) C9a' 0.098 (3)

Sigref 0.003 Sigpln 0.136 Chisq 15997.6 ===========================

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

	x	y	z	Uiso*/Ueq
O1	0.17833 (6)	0.14267 (18)	0.76379 (17)	0.0725 (6)
C1	0.12133 (10)	0.2904 (3)	0.8775 (3)	0.0805 (10)
C2	0.10878 (14)	0.3992 (4)	0.9312 (3)	0.0984 (12)
C3	0.07611 (15)	0.4689 (4)	0.8765 (5)	0.1108 (14)
C4	0.05450 (11)	0.4315 (4)	0.7678 (5)	0.1041 (13)
C4a	0.06677 (9)	0.3199 (3)	0.7141 (3)	0.0758 (9)
C4b	0.04874 (9)	0.2551 (4)	0.6043 (3)	0.0813 (10)
C5	0.01479 (10)	0.2842 (5)	0.5193 (4)	0.1099 (14)
C6	0.00347 (12)	0.2012 (7)	0.4233 (4)	0.1276 (19)
C7	0.02477 (12)	0.0901 (5)	0.4117 (3)	0.1141 (15)
C8	0.05878 (9)	0.0596 (4)	0.4948 (3)	0.0889 (11)
C8a	0.07124 (8)	0.1436 (4)	0.5904 (3)	0.0709 (9)
C9	0.10710 (8)	0.1348 (3)	0.6933 (2)	0.0612 (8)
C9a	0.10026 (9)	0.2510 (3)	0.7684 (3)	0.0658 (8)
C10	0.14762 (7)	0.1391 (3)	0.6582 (2)	0.0561 (7)
C11	0.15132 (8)	0.2677 (3)	0.5945 (2)	0.0682 (8)
C1'	0.20941 (9)	0.0919 (3)	0.4779 (2)	0.0669 (8)
C2'	0.24660 (10)	0.0655 (4)	0.4602 (3)	0.0792 (9)
C3'	0.26857 (10)	−0.0373 (4)	0.5167 (3)	0.0854 (10)
C4'	0.25369 (10)	−0.1193 (3)	0.5904 (3)	0.0801 (10)
C4a'	0.21590 (9)	−0.0962 (3)	0.6065 (2)	0.0617 (8)
C4b'	0.19111 (10)	−0.1752 (3)	0.6650 (2)	0.0674 (9)
C5'	0.19826 (12)	−0.2971 (3)	0.7214 (3)	0.0871 (11)
C6'	0.16817 (17)	−0.3594 (4)	0.7588 (3)	0.1059 (14)
C7'	0.13147 (15)	−0.3023 (4)	0.7410 (3)	0.1020 (13)
C8'	0.12388 (10)	−0.1800 (3)	0.6858 (3)	0.0804 (9)
C8a'	0.15415 (10)	−0.1156 (3)	0.6482 (2)	0.0628 (8)
C9'	0.15407 (8)	0.0164 (3)	0.5843 (2)	0.0577 (7)
C9a'	0.19422 (8)	0.0119 (3)	0.5528 (2)	0.0570 (7)
H1	0.1819	0.0679	0.7916	0.109*
H2	0.1227	0.4252	1.0053	0.118*
H3	0.0684	0.5428	0.9133	0.133*
H4	0.0323	0.4790	0.7309	0.125*
H5	−0.0001	0.3588	0.5269	0.132*
H6	−0.0189	0.2213	0.3658	0.153*
H7	0.0164	0.0345	0.3475	0.137*
H8	0.0731	−0.0162	0.4867	0.107*
H9	0.1054	0.0526	0.7366	0.073*
H1'	0.1948	0.1627	0.4399	0.080*
H2'	0.2568	0.1185	0.4091	0.095*
H3'	0.2938	−0.0519	0.5052	0.103*
H4'	0.2687	−0.1890	0.6288	0.096*
H5'	0.2231	−0.3360	0.7336	0.105*
H6'	0.1727	−0.4409	0.7964	0.127*
H7'	0.1114	−0.3461	0.7663	0.122*
H8'	0.0990	−0.1419	0.6743	0.096*
H9'	0.1334	0.0145	0.5119	0.069*
H1a	0.1438	0.2442	0.9147	0.097*
H11a	0.1451	0.3408	0.6398	0.102*
H11b	0.1334	0.2668	0.5190	0.102*
H11c	0.1778	0.2770	0.5844	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0731 (13)	0.0639 (13)	0.0694 (13)	0.0030 (11)	−0.0072 (11)	−0.0052 (11)
C1	0.107 (3)	0.078 (2)	0.061 (2)	−0.007 (2)	0.0259 (19)	−0.0016 (19)
C2	0.133 (4)	0.088 (3)	0.090 (3)	−0.013 (3)	0.060 (3)	−0.007 (2)
C3	0.118 (4)	0.087 (3)	0.154 (4)	−0.013 (3)	0.087 (3)	−0.015 (3)
C4	0.074 (2)	0.095 (3)	0.160 (4)	0.004 (2)	0.060 (3)	0.012 (3)
C4a	0.061 (2)	0.080 (2)	0.093 (3)	−0.005 (2)	0.033 (2)	0.010 (2)
C4b	0.0434 (18)	0.107 (3)	0.095 (3)	−0.004 (2)	0.0171 (19)	0.028 (2)
C5	0.061 (2)	0.126 (4)	0.139 (4)	−0.002 (2)	0.015 (3)	0.042 (3)
C6	0.064 (3)	0.180 (5)	0.123 (4)	−0.023 (3)	−0.012 (3)	0.054 (4)
C7	0.083 (3)	0.164 (5)	0.080 (3)	−0.037 (3)	−0.013 (2)	0.016 (3)
C8	0.068 (2)	0.125 (3)	0.068 (2)	−0.021 (2)	0.0022 (18)	0.006 (2)
C8a	0.0517 (18)	0.098 (3)	0.0613 (19)	−0.0133 (19)	0.0090 (15)	0.0151 (19)
C9	0.0641 (19)	0.062 (2)	0.0562 (17)	−0.0059 (15)	0.0117 (14)	0.0112 (15)
C9a	0.067 (2)	0.073 (2)	0.063 (2)	−0.0051 (17)	0.0265 (17)	0.0110 (18)
C10	0.0556 (17)	0.0560 (18)	0.0527 (16)	−0.0030 (15)	0.0032 (14)	0.0047 (14)
C11	0.072 (2)	0.0564 (19)	0.083 (2)	0.0040 (16)	0.0313 (16)	0.0111 (16)
C1'	0.073 (2)	0.0632 (19)	0.0656 (19)	−0.0034 (17)	0.0167 (16)	−0.0021 (17)
C2'	0.079 (2)	0.085 (3)	0.078 (2)	−0.009 (2)	0.0256 (19)	−0.015 (2)
C3'	0.075 (2)	0.096 (3)	0.084 (2)	0.000 (2)	0.015 (2)	−0.030 (2)
C4'	0.088 (3)	0.077 (2)	0.065 (2)	0.017 (2)	−0.0036 (18)	−0.0236 (19)
C4a'	0.077 (2)	0.0544 (19)	0.0481 (17)	0.0069 (17)	0.0031 (15)	−0.0082 (15)
C4b'	0.098 (2)	0.0498 (19)	0.0462 (16)	0.0039 (18)	−0.0006 (16)	−0.0053 (15)
C5'	0.145 (3)	0.055 (2)	0.0521 (19)	0.007 (2)	0.001 (2)	−0.0034 (17)
C6'	0.187 (5)	0.052 (2)	0.063 (2)	−0.014 (3)	−0.005 (3)	0.0082 (18)
C7'	0.162 (4)	0.070 (3)	0.070 (2)	−0.042 (3)	0.017 (3)	0.003 (2)
C8'	0.103 (3)	0.068 (2)	0.067 (2)	−0.0237 (19)	0.0122 (18)	0.0014 (18)
C8a'	0.086 (2)	0.0521 (18)	0.0456 (16)	−0.0134 (18)	0.0058 (15)	−0.0011 (14)
C9'	0.0659 (19)	0.0545 (18)	0.0472 (16)	−0.0044 (15)	0.0009 (13)	0.0036 (14)
C9a'	0.0645 (19)	0.0539 (18)	0.0494 (17)	−0.0042 (16)	0.0060 (14)	−0.0046 (14)

Geometric parameters (Å, º)

O1—C10	1.440 (3)	C6'—C7'	1.374 (5)
C1—C9a	1.379 (4)	C7'—C8'	1.390 (5)
C1—C2	1.383 (4)	C8'—C8a'	1.391 (4)
C2—C3	1.367 (5)	C8a'—C9'	1.526 (4)
C3—C4	1.376 (5)	C9'—C9a'	1.523 (4)
C4a—C9a	1.383 (4)	C9'—C10	1.554 (3)
C4a—C4	1.402 (5)	O1—H1	0.8200
C4a—C4b	1.451 (4)	C1—H1a	0.9300
C4b—C5	1.393 (5)	C2—H2	0.9300
C4b—C8a	1.401 (4)	C3—H3	0.9300
C5—C6	1.384 (6)	C4—H4	0.9300
C6—C7	1.367 (6)	C5—H5	0.9300
C7—C8	1.386 (5)	C6—H6	0.9300
C8—C8a	1.392 (4)	C7—H7	0.9300
C8a—C9	1.529 (4)	C8—H8	0.9300
C9—C9a	1.516 (4)	C9—H9	0.9800
C9—C10	1.555 (3)	C1'—H1'	0.9300
C10—C11	1.517 (3)	C2'—H2'	0.9300
C1'—C9a'	1.379 (4)	C3'—H3'	0.9300
C1'—C2'	1.381 (4)	C4'—H4'	0.9300
C2'—C3'	1.368 (5)	C5'—H5'	0.9300
C3'—C4'	1.376 (4)	C6'—H6'	0.9300
C4'—C4a'	1.389 (4)	C7'—H7'	0.9300
C4a'—C9a'	1.393 (3)	C8'—H8'	0.9300
C4a'—C4b'	1.453 (4)	C9'—H9'	0.9800
C4b'—C5'	1.392 (4)	C11—H11a	0.9600
C4b'—C8a'	1.393 (4)	C11—H11b	0.9600
C5'—C6'	1.373 (5)	C11—H11c	0.9600
C11—C10—O1	105.7 (2)	C1'—C9a'—C4a'	119.9 (3)
C9—C10—O1	108.5 (2)	C1'—C9a'—C9'	129.7 (3)
C9'—C10—O1	108.9 (2)	C4a'—C9a'—C9'	110.3 (3)
C9—C10—C11	109.6 (2)	C10—O1—H1	109.5
C9'—C10—C11	111.8 (2)	C9a—C1—H1a	120.3
C9—C10—C9'	112.1 (2)	C2—C1—H1a	120.3
C9a—C9—C10	113.6 (2)	C3—C2—H2	119.6
C9a'—C9'—C10	114.4 (2)	C1—C2—H2	119.6
C8a—C9—C10	114.8 (2)	C2—C3—H3	119.5
C8a'—C9'—C10	114.1 (2)	C4—C3—H3	119.5
C9a—C1—C2	119.5 (3)	C3—C4—H4	120.8
C2—C3—C4	121.0 (4)	C4a—C4—H4	120.8
C3—C2—C1	120.7 (4)	C6—C5—H5	120.3
C9a—C4a—C4	120.5 (4)	C4b—C5—H5	120.3
C9a—C4a—C4b	109.4 (3)	C7—C6—H6	119.5
C4—C4a—C4b	130.0 (4)	C5—C6—H6	119.5
C5—C4b—C8a	119.6 (4)	C6—C7—H7	119.7
C5—C4b—C4a	131.6 (4)	C8—C7—H7	119.7
C8a—C4b—C4a	108.8 (3)	C7—C8—H8	120.3
C3—C4—C4a	118.4 (4)	C8a—C8—H8	120.3
C6—C5—C4b	119.4 (4)	C9a—C9—H9	108.8
C7—C6—C5	120.9 (4)	C8a—C9—H9	108.8
C6—C7—C8	120.6 (4)	C10—C9—H9	108.8
C7—C8—C8a	119.3 (4)	C10—C11—H11a	109.5
C8—C8a—C4b	120.0 (3)	C10—C11—H11b	109.5
C8—C8a—C9	130.4 (3)	H11a—C11—H11b	109.5
C4b—C8a—C9	109.5 (3)	C10—C11—H11c	109.5
C9a—C9—C8a	101.7 (2)	H11a—C11—H11c	109.5
C1—C9a—C4a	119.9 (3)	H11b—C11—H11c	109.5
C1—C9a—C9	129.7 (3)	C9a'—C1'—H1'	120.4
C4a—C9a—C9	110.4 (3)	C2'—C1'—H1'	120.4
C9a'—C1'—C2'	119.2 (3)	C3'—C2'—H2'	119.5
C3'—C2'—C1'	121.0 (3)	C1'—C2'—H2'	119.5
C2'—C3'—C4'	120.7 (3)	C2'—C3'—H3'	119.7
C3'—C4'—C4a'	119.0 (3)	C4'—C3'—H3'	119.7
C4'—C4a'—C9a'	120.2 (3)	C3'—C4'—H4'	120.5
C4'—C4a'—C4b'	130.6 (3)	C4a'—C4'—H4'	120.5
C9a'—C4a'—C4b'	108.9 (3)	C6'—C5'—H5'	120.4
C5'—C4b'—C8a'	120.7 (3)	C4b'—C5'—H5'	120.4
C5'—C4b'—C4a'	130.2 (3)	C7'—C6'—H6'	119.7
C8a'—C4b'—C4a'	108.8 (3)	C5'—C6'—H6'	119.7
C6'—C5'—C4b'	119.1 (4)	C6'—C7'—H7'	119.5
C7'—C6'—C5'	120.6 (4)	C8'—C7'—H7'	119.5
C6'—C7'—C8'	121.1 (4)	C7'—C8'—H8'	120.6
C7'—C8'—C8a'	118.9 (4)	C8a'—C8'—H8'	120.6
C8'—C8a'—C4b'	119.6 (3)	C9a'—C9'—H9'	109.0
C8'—C8a'—C9'	130.1 (3)	C8a'—C9'—H9'	109.0
C4b'—C8a'—C9'	110.3 (3)	C10—C9'—H9'	109.0
C9a'—C9'—C8a'	101.0 (2)
C1—C9a—C9—C10	−60.7 (4)	C9a—C9—C10—O1	58.1 (3)
C1'—C9a'—C9'—C10	−68.7 (3)	C8a—C9—C10—O1	174.6 (2)
C8—C8a—C9—C10	61.6 (4)	C9a—C9—C10—C11	−56.9 (3)
C8'—C8a'—C9'—C10	66.3 (4)	C8a—C9—C10—C11	59.6 (3)
C9a—C9—C10—C9'	178.4 (2)	C9a'—C1'—C2'—C3'	−0.8 (4)
C9a'—C9'—C10—C9	−177.0 (2)	C1'—C2'—C3'—C4'	1.7 (5)
C8a—C9—C10—C9'	−65.1 (3)	C2'—C3'—C4'—C4a'	0.1 (5)
C8a'—C9'—C10—C9	−61.4 (3)	C3'—C4'—C4a'—C9a'	−2.8 (4)
C1—C2—C3—C4	1.2 (6)	C3'—C4'—C4a'—C4b'	170.7 (3)
C9a—C4a—C4b—C5	179.1 (3)	C4'—C4a'—C4b'—C5'	−0.2 (5)
C4—C4a—C4b—C5	1.2 (6)	C9a'—C4a'—C4b'—C5'	173.8 (3)
C9a—C4a—C4b—C8a	0.4 (3)	C4'—C4a'—C4b'—C8a'	−174.4 (3)
C4—C4a—C4b—C8a	−177.5 (3)	C9a'—C4a'—C4b'—C8a'	−0.4 (3)
C9a—C1—C2—C3	−1.0 (5)	C8a'—C4b'—C5'—C6'	1.0 (4)
C2—C3—C4—C4a	−0.1 (5)	C4a'—C4b'—C5'—C6'	−172.6 (3)
C9a—C4a—C4—C3	−1.2 (5)	C4b'—C5'—C6'—C7'	−0.1 (5)
C4b—C4a—C4—C3	176.5 (3)	C5'—C6'—C7'—C8'	−0.5 (5)
C8a—C4b—C5—C6	1.0 (5)	C6'—C7'—C8'—C8a'	0.2 (5)
C4b—C5—C6—C7	1.0 (6)	C7'—C8'—C8a'—C4b'	0.8 (4)
C5—C6—C7—C8	−1.5 (6)	C7'—C8'—C8a'—C9'	178.9 (3)
C6—C7—C8—C8a	−0.2 (5)	C5'—C4b'—C8a'—C8'	−1.4 (4)
C7—C8—C8a—C4b	2.3 (4)	C4a'—C4b'—C8a'—C8'	173.5 (2)
C7—C8—C8a—C9	−179.8 (3)	C5'—C4b'—C8a'—C9'	−179.8 (2)
C4a—C4b—C5—C6	−177.6 (3)	C4a'—C4b'—C8a'—C9'	−5.0 (3)
C5—C4b—C8a—C8	−2.7 (4)	C8'—C8a'—C9'—C9a'	−170.5 (3)
C4a—C4b—C8a—C8	176.2 (3)	C4b'—C8a'—C9'—C9a'	7.8 (3)
C5—C4b—C8a—C9	178.9 (3)	C2'—C1'—C9a'—C4a'	−1.9 (4)
C4a—C4b—C8a—C9	−2.1 (3)	C2'—C1'—C9a'—C9'	−177.9 (3)
C8—C8a—C9—C9a	−175.3 (3)	C4'—C4a'—C9a'—C1'	3.7 (4)
C4b—C8a—C9—C9a	2.9 (3)	C4b'—C4a'—C9a'—C1'	−171.0 (2)
C4b—C8a—C9—C10	−120.2 (3)	C4'—C4a'—C9a'—C9'	−179.6 (2)
C2—C1—C9a—C4a	−0.3 (4)	C4b'—C4a'—C9a'—C9'	5.6 (3)
C2—C1—C9a—C9	−178.3 (3)	C8a'—C9'—C9a'—C1'	168.2 (3)
C4—C4a—C9a—C1	1.4 (4)	C8a'—C9'—C9a'—C4a'	−8.0 (3)
C4b—C4a—C9a—C1	−176.7 (3)	C10—C9'—C9a'—C4a'	115.0 (2)
C4—C4a—C9a—C9	179.7 (3)	C4b'—C8a'—C9'—C10	−115.4 (2)
C4b—C4a—C9a—C9	1.6 (3)	C9a'—C9'—C10—O1	−57.0 (3)
C8a—C9—C9a—C1	175.4 (3)	C8a'—C9'—C10—O1	58.7 (3)
C8a—C9—C9a—C4a	−2.7 (3)	C9a'—C9'—C10—C11	59.4 (3)
C10—C9—C9a—C4a	121.2 (2)	C8a'—C9'—C10—C11	175.1 (2)