9-(para-tert-Butyl­phenyl)-9-fluorenol

The title compound, C₂₃H₂₂O, is composed of two slightly different molecular conformations in its asymmetric unit, one conformation hydrogen bonded to the other via their OH groups. The two molecular conformers are reproduced by an inversion center and hydrogen bonded through an O—H...π(fluorene) bond, thus producing groups of four hydrogen-bonded mol­ecules. The cooled melted crystals failed to recrystallize, but solution NMR showed that no chemical decomposition had occurred during the melting.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.128
• Data-to-parameter ratio = 14.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_420  Alert B D-H Without Acceptor       O1     -   H1                ?


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

S1. Comment

We previously reported the crystal structure of sp-9-(ortho-tert-butylphenyl)-9-fluorenol (Robinson et al., 1998; see also Meyers et al., 1999) as well as that of 9-(ortho-isopropylphenyl)-9-fluorenol (Hou et al., 1999). We wanted to compare the crystal structure of the title compound, (I), with that of its ortho-tert-butyl isomer. The structure of (I), with the atom numbering, is shown in Fig. 1.

As illustrated, compound (I) crystallizes in two slightly different conformations within the asymmetric unit, molecules numbered 1 and 2. Fig. 2 shows that molecule 1 is hydrogen bonded to molecule 2 via conventional O—H···O interaction, the O atom of molecule 2 being the donor, and the O atom of molecule 1 being the acceptor. In addition, there appears to be a strong interaction between the hydroxyl H atom of molecule 1 and the π-electrons nearest to C4 of the fluorene ring of a centrosymmetrically related molecule 1, an interaction which may be interpreted as an O—H···π(arene) bond (Ferguson et al., 1994). The end result is a cluster of four hydrogen-bonded molecules situated about an inversion center, denoted by a plus sign at the center of Fig. 2. Detailed hydrogen-bonding geometry is given in Table 1. Since the inversion center is located at the cell origin each cell corner will be surrounded by an identical group of four molecules, thereby defining the molecular packing of the structure, shown in Fig. 3. It is interesting to note that the related 9-(ortho-tert-butylphenyl)-9-fluorenol (Robinson et al., 1998) likewise crystallizes in two different molecular conformations and also shows the same type of intermolecular O—H···O—H hydrogen bonding between the two different molecular conformers. We have recently re-examined the X-ray data of the ortho-tert-butyl isomer and feel confident now to suggest that this compound also exhibits O—H···π(arene) bonding but, in this case, it is between the two different molecular conformers. It is interesting to find the hydrogen-bonding similarities exhibited by these two structures, since the 9-(ortho-tert-butylphenyl)-9-fluorenol has considerable steric and rotational constraints while, in contrast, (I) has no such encumberances. We therefore must refute the statement that we previously reported for 9-(ortho-tert-butylphenyl)-9-fluorenol (Robinson et al., 1998), viz. `It is reasonable to believe that stabilization of the molecular packing is attained via the intermolecular H bonding which, because of the large steric effects, is best enabled between structures (1a) and (1 b).'

While compound (I) melted quite sharply, the melt failed to crystallize on cooling or even in an ice bath, over several days, although its NMR was identical to that of crystalline (I). The same phenomenon was exhibited by isomeric 9-(ortho-tert-butylphenyl)-9-fluorenol, although its melt did crystallize after standing for several days. It is possible that this phenomenon is associated with the rather complex O—H···O—H and O—H···π(fluorene) hydrogen bonding and resulting molecular packing patterns, which are similar in both compounds. It might be energetically unfavorable for these molecules in the melt to readily reorganize into the complex hydrogen-bonded pattern required for their crystallization, a pattern much more easily attained from a slowly evaporating solution.

S2. Experimental

A mixture of magnesium (0.2866 g, 11.78 mmol), freshly distilled tetrahydrofuran (20 ml), and 1,2-dibromoethane (0.30 ml, 3.48 mmol), maintained under argon, was gently heated until bubbles appeared on the Mg surface. para-Bromo-tert-butylbenzene (1.774 g, 8.33 mmol) was injected, the mixture was refluxed for 30 min, and a solution of 9-fluorenone (1.00 g, 5.56 mmol) in tetrahydrofuran (15 ml) was added. This mixture was refluxed for 5 h, cooled, diluted with water then 6 N H₂SO₄ and extracted with ether. The extracts were dried and concentrated to a yellow oil, which was purified by column chromatography (2:1 hexanes–ethyl acetate). Concentration of the major fraction left an oil which, after several days, provided a yellow solid, 1.426 g (84.9% yield), yellow crystals (from hexanes), m.p. 392–395 K (literature m.p. 391–393 K; Weber, Dörpinghaus & Csöregh, 1990). The melt failed to crystallize on cooling, even in an ice bath, but its NMR was identical to that of the crystalline product, showing that no decomposition had occurred on melting. NMR (CDCl₃): ¹H, δ 1.27 (s, 9 H), 2.423 (s, 1 H), 7.22–7.38 (m, 9 H), 7.64–7.67 (m, 3 H); ¹³C, δ 31.30, 34.39, 83.56, 120.04, 124.81, 125.03, 125.12, 128.35, 128.99, 139.55, 140.06, 149.99, 150.41.

S3. Refinement

The rotational orientations of the methyl H atoms in molecule 1 (Fig. 1) were refined by the circular Fourier method available in SHELXL97 (Sheldrick, 1997); the hydroxyl H atom position for both molecules was determined in a similar manner. The tertiary butyl group of molecule 2 is somewhat rotationally disordered and thus its H atoms were placed in geometrically favorable positions but were not refined. All H atoms are riding with C—H distances ranging from 0.82 to 0.96 Å.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON.

Figures

	Fig. 1. The molecular structure and atom numbering scheme for (I), with displacement ellipsoids at the 50% probablilty level. The two molecules in the asymmetric unit are shown in approximately the same orientation for ease of comparison and do not represent their actual juxtaposition in the structure.
	Fig. 2. Hydrogen bonding in (I). The two crystallographically distinct hydrogen bonds produce groups of four hydrogen-bonded molecules around the inversion centers located at the corners of the unit cell. Atoms or molecules marked with an asterisk (*), hash (#), or caret (^) are at the symmetry positions (x, y − 1, z), (-x, 1 − y, 2 − z), and (-x, −y, 2 − z), respectively; the plus (+) represents an inversion center.
	Fig. 3. The molecular packing in (I) as viewed down the c* axis. Note the groupings of four hydrogen-bonded molecules about each cell corner.

9-(para-tert-Butylphenyl)-9-fluorenol

Crystal data

C23H22O	F(000) = 672
Mr = 314.41	Dx = 1.181 Mg m^−3
Triclinic, P1	Melting point = 392–395 K
a = 10.2843 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 12.1135 (2) Å	Cell parameters from 5098 reflections
c = 14.5033 (2) Å	θ = 2.3–27.8°
α = 82.915 (1)°	µ = 0.07 mm^−1
β = 80.656 (1)°	T = 170 K
γ = 87.563 (1)°	Prism, pale yellow
V = 1768.75 (5) Å^3	0.36 × 0.33 × 0.20 mm
Z = 4

Data collection

Bruker CCD area-detector diffractometer	4292 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ϕ and ω scans	h = −12→12
20884 measured reflections	k = −14→14
6224 independent reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0651P)^2 + 0.1886P] where P = (Fo^2 + 2Fc^2)/3
6224 reflections	(Δ/σ)max < 0.001
438 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.28797 (12)	−0.04523 (9)	0.92572 (8)	0.0331 (3)
C1	0.06054 (19)	0.05220 (15)	0.81484 (13)	0.0354 (4)
C2	−0.0671 (2)	0.08518 (16)	0.80304 (14)	0.0414 (5)
C3	−0.13864 (19)	0.15862 (16)	0.85911 (14)	0.0406 (5)
C4	−0.08574 (18)	0.19832 (15)	0.93043 (13)	0.0357 (5)
C4A	0.04015 (17)	0.16182 (13)	0.94523 (12)	0.0299 (4)
C4B	0.11604 (17)	0.18015 (13)	1.01953 (12)	0.0290 (4)
C5	0.08287 (19)	0.23499 (15)	1.09947 (13)	0.0366 (5)
C6	0.1710 (2)	0.23047 (16)	1.16231 (14)	0.0404 (5)
C7	0.29009 (19)	0.17193 (16)	1.14736 (14)	0.0399 (5)
C8	0.32502 (19)	0.11853 (15)	1.06689 (13)	0.0354 (4)
C8A	0.23762 (17)	0.12393 (13)	1.00357 (12)	0.0288 (4)
C9	0.25194 (17)	0.07046 (13)	0.91236 (12)	0.0288 (4)
C9A	0.11371 (17)	0.09179 (14)	0.88579 (12)	0.0300 (4)
C10	0.35697 (17)	0.12665 (14)	0.83613 (12)	0.0279 (4)
C11	0.45848 (17)	0.06810 (14)	0.78887 (13)	0.0324 (4)
C12	0.55235 (18)	0.12193 (15)	0.71964 (13)	0.0342 (4)
C13	0.54835 (17)	0.23588 (14)	0.69511 (12)	0.0286 (4)
C14	0.44411 (19)	0.29426 (15)	0.74315 (13)	0.0380 (5)
C15	0.35117 (19)	0.24137 (15)	0.81179 (14)	0.0387 (5)
C16	0.65144 (18)	0.29805 (15)	0.62091 (12)	0.0329 (4)
C17	0.5849 (2)	0.37132 (17)	0.54769 (14)	0.0459 (5)
C18	0.7293 (2)	0.37222 (17)	0.66990 (15)	0.0491 (6)
C19	0.7496 (2)	0.21884 (17)	0.56987 (14)	0.0500 (6)
H1	0.2426	−0.0753	0.9732	0.050*
H1A	0.1092	0.0046	0.7760	0.042*
H2	−0.1053	0.0576	0.7569	0.050*
H3	−0.2231	0.1815	0.8488	0.049*
H4	−0.1334	0.2482	0.9675	0.043*
H5	0.0030	0.2739	1.1103	0.044*
H6	0.1502	0.2673	1.2156	0.048*
H7	0.3470	0.1683	1.1914	0.048*
H8	0.4053	0.0802	1.0561	0.042*
H11	0.4647	−0.0087	0.8033	0.039*
H12	0.6198	0.0799	0.6890	0.041*
H14	0.4372	0.3710	0.7284	0.046*
H15	0.2833	0.2831	0.8424	0.046*
H17A	0.5351	0.3257	0.5171	0.069*
H17B	0.6508	0.4095	0.5018	0.069*
H17C	0.5269	0.4247	0.5782	0.069*
H18A	0.7938	0.4120	0.6239	0.074*
H18B	0.7727	0.3268	0.7153	0.074*
H18C	0.6700	0.4242	0.7011	0.074*
H19A	0.7035	0.1730	0.5370	0.075*
H19B	0.7930	0.1726	0.6149	0.075*
H19C	0.8139	0.2612	0.5257	0.075*
O1'	0.22095 (12)	0.81038 (10)	0.80260 (9)	0.0348 (3)
C1'	0.40119 (18)	0.69327 (17)	0.95036 (13)	0.0382 (5)
C2'	0.4017 (2)	0.63328 (19)	1.03864 (14)	0.0481 (6)
C3'	0.3287 (2)	0.5385 (2)	1.06536 (15)	0.0542 (6)
C4'	0.2542 (2)	0.50033 (17)	1.00573 (15)	0.0477 (5)
C4A'	0.25258 (17)	0.55975 (15)	0.91731 (13)	0.0334 (4)
C4B'	0.18234 (17)	0.54095 (14)	0.84080 (13)	0.0332 (4)
C5'	0.09488 (19)	0.45932 (16)	0.83357 (16)	0.0456 (5)
C6'	0.0416 (2)	0.46175 (19)	0.75214 (19)	0.0563 (6)
C7'	0.0720 (2)	0.5457 (2)	0.67930 (17)	0.0559 (6)
C8'	0.15744 (19)	0.62937 (17)	0.68613 (14)	0.0426 (5)
C8A'	0.21194 (17)	0.62576 (14)	0.76687 (12)	0.0303 (4)
C9'	0.30074 (17)	0.71102 (14)	0.79346 (12)	0.0289 (4)
C9A'	0.32564 (17)	0.65627 (14)	0.89023 (12)	0.0304 (4)
C10'	0.42488 (17)	0.73504 (13)	0.72157 (12)	0.0276 (4)
C11'	0.43504 (18)	0.83302 (15)	0.66085 (13)	0.0373 (5)
C12'	0.54749 (19)	0.85501 (16)	0.59434 (14)	0.0412 (5)
C13'	0.65353 (18)	0.78098 (15)	0.58501 (12)	0.0327 (4)
C14'	0.64180 (18)	0.68266 (15)	0.64652 (13)	0.0362 (5)
C15'	0.53011 (18)	0.66017 (15)	0.71275 (13)	0.0347 (5)
C16'	0.77835 (19)	0.80600 (17)	0.51269 (13)	0.0404 (5)
C17'	0.8841 (2)	0.8442 (3)	0.56314 (19)	0.0826 (9)
C18'	0.7546 (3)	0.9003 (3)	0.43683 (18)	0.0934 (11)
C19'	0.8273 (3)	0.7044 (2)	0.4655 (2)	0.0958 (11)
H1'	0.2526	0.8499	0.8349	0.052*
H1A'	0.4507	0.7570	0.9322	0.046*
H2'	0.4518	0.6574	1.0799	0.058*
H3'	0.3298	0.4997	1.1247	0.065*
H4'	0.2058	0.4360	1.0241	0.057*
H5'	0.0726	0.4036	0.8832	0.055*
H6'	−0.0154	0.4063	0.7462	0.068*
H7'	0.0349	0.5464	0.6249	0.067*
H8'	0.1771	0.6863	0.6372	0.051*
H11'	0.3657	0.8849	0.6646	0.045*
H12'	0.5514	0.9218	0.5548	0.049*
H14'	0.7110	0.6306	0.6430	0.043*
H15'	0.5259	0.5933	0.7521	0.042*
H17A'	0.8527	0.9090	0.5927	0.124*
H17B'	0.9622	0.8618	0.5185	0.124*
H17C'	0.9042	0.7858	0.6101	0.124*
H18A'	0.7234	0.9656	0.4658	0.140*
H18B'	0.6899	0.8785	0.4022	0.140*
H18C'	0.8355	0.9161	0.3948	0.140*
H19A'	0.8431	0.6444	0.5124	0.144*
H19B'	0.9077	0.7211	0.4231	0.144*
H19C'	0.7621	0.6831	0.4310	0.144*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0394 (8)	0.0260 (6)	0.0313 (7)	−0.0032 (6)	−0.0001 (6)	0.0010 (5)
C1	0.0401 (11)	0.0364 (10)	0.0291 (10)	−0.0039 (9)	−0.0064 (9)	0.0004 (8)
C2	0.0442 (12)	0.0451 (12)	0.0351 (11)	−0.0098 (10)	−0.0129 (10)	0.0071 (9)
C3	0.0301 (10)	0.0451 (12)	0.0420 (12)	−0.0058 (9)	−0.0066 (9)	0.0154 (9)
C4	0.0285 (10)	0.0332 (10)	0.0403 (12)	−0.0034 (8)	0.0020 (9)	0.0066 (8)
C4A	0.0277 (10)	0.0263 (9)	0.0320 (10)	−0.0072 (8)	0.0025 (8)	0.0038 (8)
C4B	0.0280 (10)	0.0253 (9)	0.0306 (10)	−0.0078 (8)	0.0041 (8)	−0.0004 (7)
C5	0.0330 (11)	0.0320 (10)	0.0408 (12)	−0.0050 (8)	0.0077 (9)	−0.0056 (8)
C6	0.0442 (12)	0.0432 (11)	0.0323 (11)	−0.0122 (10)	0.0053 (10)	−0.0103 (9)
C7	0.0382 (11)	0.0472 (12)	0.0340 (11)	−0.0097 (9)	−0.0031 (9)	−0.0040 (9)
C8	0.0327 (10)	0.0379 (11)	0.0345 (11)	−0.0039 (8)	−0.0024 (9)	−0.0028 (8)
C8A	0.0295 (10)	0.0259 (9)	0.0289 (10)	−0.0062 (8)	0.0010 (8)	−0.0003 (7)
C9	0.0323 (10)	0.0240 (9)	0.0292 (10)	−0.0007 (8)	−0.0032 (8)	−0.0022 (7)
C9A	0.0301 (10)	0.0284 (9)	0.0291 (10)	−0.0074 (8)	−0.0010 (8)	0.0042 (8)
C10	0.0283 (10)	0.0291 (9)	0.0265 (10)	−0.0015 (8)	−0.0046 (8)	−0.0033 (7)
C11	0.0325 (10)	0.0257 (9)	0.0367 (11)	0.0009 (8)	−0.0019 (9)	0.0004 (8)
C12	0.0296 (10)	0.0344 (10)	0.0359 (11)	0.0040 (8)	0.0013 (8)	−0.0032 (8)
C13	0.0277 (10)	0.0339 (10)	0.0241 (9)	−0.0020 (8)	−0.0056 (8)	−0.0006 (7)
C14	0.0418 (12)	0.0272 (10)	0.0407 (12)	−0.0021 (9)	0.0020 (9)	0.0012 (8)
C15	0.0388 (11)	0.0296 (10)	0.0421 (12)	0.0025 (9)	0.0086 (9)	−0.0028 (8)
C16	0.0305 (10)	0.0375 (10)	0.0287 (10)	−0.0027 (8)	−0.0031 (8)	0.0027 (8)
C17	0.0429 (12)	0.0561 (13)	0.0345 (12)	−0.0020 (10)	−0.0047 (10)	0.0091 (10)
C18	0.0484 (13)	0.0540 (13)	0.0439 (13)	−0.0193 (11)	−0.0098 (10)	0.0078 (10)
C19	0.0428 (13)	0.0551 (13)	0.0423 (13)	0.0033 (11)	0.0112 (10)	0.0078 (10)
O1'	0.0318 (7)	0.0333 (7)	0.0388 (8)	0.0003 (6)	−0.0017 (6)	−0.0082 (6)
C1'	0.0291 (10)	0.0502 (12)	0.0356 (11)	−0.0011 (9)	−0.0019 (9)	−0.0110 (9)
C2'	0.0397 (12)	0.0735 (16)	0.0328 (12)	0.0065 (11)	−0.0091 (10)	−0.0108 (11)
C3'	0.0554 (14)	0.0696 (15)	0.0329 (12)	0.0089 (12)	−0.0068 (11)	0.0092 (11)
C4'	0.0464 (13)	0.0462 (12)	0.0446 (13)	−0.0016 (10)	−0.0007 (11)	0.0096 (10)
C4A'	0.0287 (10)	0.0360 (10)	0.0331 (11)	0.0006 (8)	0.0000 (8)	−0.0018 (8)
C4B'	0.0272 (10)	0.0280 (9)	0.0432 (11)	−0.0007 (8)	−0.0003 (9)	−0.0058 (8)
C5'	0.0366 (12)	0.0318 (11)	0.0669 (15)	−0.0055 (9)	−0.0033 (11)	−0.0049 (10)
C6'	0.0439 (13)	0.0486 (13)	0.0832 (19)	−0.0111 (11)	−0.0153 (13)	−0.0235 (13)
C7'	0.0460 (13)	0.0701 (16)	0.0598 (15)	−0.0036 (12)	−0.0194 (12)	−0.0247 (13)
C8'	0.0394 (12)	0.0517 (12)	0.0386 (12)	−0.0056 (10)	−0.0075 (10)	−0.0095 (9)
C8A'	0.0243 (9)	0.0339 (10)	0.0324 (10)	−0.0005 (8)	−0.0004 (8)	−0.0083 (8)
C9'	0.0267 (9)	0.0292 (9)	0.0301 (10)	−0.0014 (8)	−0.0016 (8)	−0.0042 (7)
C9A'	0.0245 (9)	0.0365 (10)	0.0287 (10)	−0.0001 (8)	0.0010 (8)	−0.0057 (8)
C10'	0.0286 (10)	0.0278 (9)	0.0265 (10)	−0.0028 (8)	−0.0042 (8)	−0.0036 (7)
C11'	0.0312 (10)	0.0370 (11)	0.0394 (11)	0.0051 (9)	0.0011 (9)	0.0018 (9)
C12'	0.0409 (12)	0.0361 (11)	0.0401 (12)	0.0002 (9)	0.0035 (9)	0.0078 (9)
C13'	0.0316 (10)	0.0400 (11)	0.0264 (10)	−0.0047 (9)	−0.0019 (8)	−0.0054 (8)
C14'	0.0323 (11)	0.0376 (11)	0.0357 (11)	0.0061 (9)	−0.0005 (9)	−0.0016 (8)
C15'	0.0393 (11)	0.0294 (10)	0.0314 (11)	0.0005 (8)	0.0015 (9)	0.0022 (8)
C16'	0.0351 (11)	0.0512 (12)	0.0314 (11)	−0.0024 (9)	0.0017 (9)	0.0003 (9)
C17'	0.0470 (15)	0.135 (3)	0.0625 (17)	−0.0305 (16)	0.0098 (13)	−0.0145 (17)
C18'	0.0620 (17)	0.132 (3)	0.0591 (17)	0.0152 (17)	0.0232 (14)	0.0445 (17)
C19'	0.091 (2)	0.087 (2)	0.091 (2)	−0.0107 (17)	0.0563 (18)	−0.0278 (17)

Geometric parameters (Å, º)

O1—C9	1.4321 (19)	O1'—C9'	1.435 (2)
C1—C9A	1.384 (3)	C1'—C9A'	1.382 (3)
C1—C2	1.387 (3)	C1'—C2'	1.393 (3)
C2—C3	1.386 (3)	C2'—C3'	1.379 (3)
C3—C4	1.387 (3)	C3'—C4'	1.376 (3)
C4—C4A	1.391 (2)	C4'—C4A'	1.393 (3)
C4A—C9A	1.396 (2)	C4A'—C9A'	1.397 (2)
C4A—C4B	1.472 (3)	C4A'—C4B'	1.463 (3)
C4B—C5	1.394 (2)	C4B'—C5'	1.389 (3)
C4B—C8A	1.398 (2)	C4B'—C8A'	1.395 (2)
C5—C6	1.381 (3)	C8'—C8A'	1.373 (3)
C6—C7	1.389 (3)	C5'—C6'	1.377 (3)
C7—C8	1.393 (3)	C6'—C7'	1.379 (3)
C8A—C8	1.380 (2)	C7'—C8'	1.392 (3)
C8A—C9	1.527 (2)	C8A'—C9'	1.530 (2)
C9—C10	1.530 (2)	C9A'—C9'	1.532 (2)
C9—C9A	1.536 (2)	C9'—C10'	1.525 (2)
C10—C11	1.374 (2)	C10'—C15'	1.382 (2)
C10—C15	1.392 (2)	C10'—C11'	1.385 (2)
C11—C12	1.394 (2)	C11'—C12'	1.393 (3)
C12—C13	1.383 (2)	C12'—C13'	1.382 (3)
C13—C14	1.396 (2)	C13'—C14'	1.394 (3)
C14—C15	1.379 (3)	C13'—C16'	1.535 (3)
C13—C16	1.532 (2)	C14'—C15'	1.386 (3)
C16—C17	1.529 (2)	C16'—C19'	1.510 (3)
C16—C18	1.535 (3)	C16'—C17'	1.522 (3)
C16—C19	1.529 (3)	C16'—C18'	1.526 (3)
O1—H1	0.8200	O1'—H1'	0.8200
C1—H1A	0.9300	C1'—H1A'	0.9300
C2—H2	0.9300	C2'—H2'	0.9300
C3—H3	0.9300	C3'—H3'	0.9300
C4—H4	0.9300	C4'—H4'	0.9300
C5—H5	0.9300	C5'—H5'	0.9300
C6—H6	0.9300	C6'—H6'	0.9300
C7—H7	0.9300	C7'—H7'	0.9300
C8—H8	0.9300	C8'—H8'	0.9300
C11—H11	0.9300	C11'—H11'	0.9300
C12—H12	0.9300	C12'—H12'	0.9300
C14—H14	0.9300	C14'—H14'	0.9300
C15—H15	0.9300	C15'—H15'	0.9300
C17—H17A	0.9600	C17'—H17A'	0.9600
C17—H17B	0.9600	C17'—H17B'	0.9600
C17—H17C	0.9600	C17'—H17C'	0.9600
C18—H18A	0.9600	C18'—H18A'	0.9600
C18—H18B	0.9600	C18'—H18B'	0.9600
C18—H18C	0.9600	C18'—H18C'	0.9600
C19—H19A	0.9600	C19'—H19A'	0.9600
C19—H19B	0.9600	C19'—H19B'	0.9600
C19—H19C	0.9600	C19'—H19C'	0.9600
C9A—C1—C2	118.43 (18)	C9A—C1—H1A	120.8
C3—C2—C1	120.92 (19)	C2—C1—H1A	120.8
C2—C3—C4	120.78 (18)	C3—C2—H2	119.5
C3—C4—C4A	118.55 (18)	C1—C2—H2	119.5
C4—C4A—C9A	120.24 (17)	C2—C3—H3	119.6
C4—C4A—C4B	130.94 (17)	C4—C3—H3	119.6
C6—C5—C4B	118.70 (18)	C3—C4—H4	120.7
C9A—C4A—C4B	108.77 (15)	C4A—C4—H4	120.7
C5—C4B—C8A	119.86 (17)	C6—C5—H5	120.6
C5—C4B—C4A	131.38 (16)	C4B—C5—H5	120.6
C8A—C4B—C4A	108.63 (15)	C5—C6—H6	119.4
C5—C6—C7	121.16 (18)	C7—C6—H6	119.4
C6—C7—C8	120.51 (19)	C6—C7—H7	119.7
C8—C8A—C4B	121.37 (16)	C8—C7—H7	119.7
C8—C8A—C9	128.07 (16)	C8A—C8—H8	120.8
C4B—C8A—C9	110.52 (15)	C7—C8—H8	120.8
C8A—C8—C7	118.36 (18)	C10—C11—H11	119.5
O1—C9—C8A	112.17 (14)	C12—C11—H11	119.5
O1—C9—C10	107.16 (13)	C13—C12—H12	118.9
C8A—C9—C10	111.97 (14)	C11—C12—H12	118.9
O1—C9—C9A	113.30 (14)	C15—C14—H14	119.1
C8A—C9—C9A	101.28 (14)	C13—C14—H14	119.1
C10—C9—C9A	111.02 (13)	C14—C15—H15	119.4
C1—C9A—C4A	120.94 (17)	C10—C15—H15	119.4
C1—C9A—C9	128.91 (16)	C16—C17—H17A	109.5
C4A—C9A—C9	110.14 (15)	C16—C17—H17B	109.5
C11—C10—C15	117.47 (16)	H17A—C17—H17B	109.5
C11—C10—C9	122.58 (15)	C16—C17—H17C	109.5
C15—C10—C9	119.95 (15)	H17A—C17—H17C	109.5
C10—C11—C12	121.08 (16)	H17B—C17—H17C	109.5
C13—C12—C11	122.11 (17)	C16—C18—H18A	109.5
C12—C13—C14	116.22 (16)	C16—C18—H18B	109.5
C12—C13—C16	123.50 (16)	H18A—C18—H18B	109.5
C14—C13—C16	120.27 (15)	C16—C18—H18C	109.5
C15—C14—C13	121.85 (17)	H18A—C18—H18C	109.5
C14—C15—C10	121.26 (17)	H18B—C18—H18C	109.5
C17—C16—C19	108.40 (15)	C16—C19—H19A	109.5
C17—C16—C13	110.59 (15)	C16—C19—H19B	109.5
C19—C16—C13	112.29 (15)	H19A—C19—H19B	109.5
C17—C16—C18	108.85 (16)	C16—C19—H19C	109.5
C19—C16—C18	107.87 (16)	H19A—C19—H19C	109.5
C13—C16—C18	108.76 (15)	H19B—C19—H19C	109.5
C9A'—C1'—C2'	118.76 (19)	C9'—O1'—H1'	109.5
C3'—C2'—C1'	120.6 (2)	C9A'—C1'—H1A'	120.6
C4'—C3'—C2'	121.14 (19)	C2'—C1'—H1A'	120.6
C3'—C4'—C4A'	118.8 (2)	C4'—C3'—H3'	119.4
C4'—C4A'—C9A'	120.23 (18)	C2'—C3'—H3'	119.4
C4'—C4A'—C4B'	131.09 (18)	C3'—C2'—H2'	119.7
C9A'—C4A'—C4B'	108.67 (15)	C1'—C2'—H2'	119.7
C5'—C4B'—C8A'	119.71 (18)	C3'—C4'—H4'	120.6
C5'—C4B'—C4A'	131.34 (18)	C4A'—C4'—H4'	120.6
C8A'—C4B'—C4A'	108.92 (15)	C8A'—C8'—H8'	120.8
C6'—C5'—C4B'	119.3 (2)	C7'—C8'—H8'	120.8
C5'—C6'—C7'	120.5 (2)	C6'—C5'—H5'	120.4
C6'—C7'—C8'	120.9 (2)	C4B'—C5'—H5'	120.4
C8A'—C8'—C7'	118.4 (2)	C5'—C6'—H6'	119.7
C8'—C8A'—C4B'	121.17 (17)	C7'—C6'—H6'	119.7
C8'—C8A'—C9'	128.11 (17)	C6'—C7'—H7'	119.5
C4B'—C8A'—C9'	110.60 (15)	C8'—C7'—H7'	119.5
C1'—C9A'—C4A'	120.47 (17)	C10'—C11'—H11'	119.5
C1'—C9A'—C9'	128.83 (17)	C12'—C11'—H11'	119.5
C4A'—C9A'—C9'	110.61 (15)	C11'—C12'—H12'	118.9
O1'—C9'—C10'	110.43 (13)	C13'—C12'—H12'	118.9
O1'—C9'—C8A'	105.80 (13)	C15'—C14'—H14'	119.0
C10'—C9'—C8A'	113.69 (14)	C13'—C14'—H14'	119.0
O1'—C9'—C9A'	110.50 (14)	C10'—C15'—H15'	119.3
C10'—C9'—C9A'	114.77 (14)	C14'—C15'—H15'	119.3
C8A'—C9'—C9A'	100.98 (14)	C16'—C17'—H17A'	109.5
C15'—C10'—C11'	117.27 (16)	C16'—C17'—H17B'	109.5
C15'—C10'—C9'	122.02 (15)	H17A'—C17'—H17B'	109.5
C11'—C10'—C9'	120.69 (15)	C16'—C17'—H17C'	109.5
C10'—C11'—C12'	121.03 (17)	H17A'—C17'—H17C'	109.5
C13'—C12'—C11'	122.25 (17)	H17B'—C17'—H17C'	109.5
C12'—C13'—C14'	116.07 (17)	C16'—C18'—H18A'	109.5
C12'—C13'—C16'	122.24 (16)	C16'—C18'—H18B'	109.5
C14'—C13'—C16'	121.68 (16)	H18A'—C18'—H18B'	109.5
C15'—C14'—C13'	121.98 (17)	C16'—C18'—H18C'	109.5
C10'—C15'—C14'	121.40 (16)	H18A'—C18'—H18C'	109.5
C19'—C16'—C17'	109.8 (2)	H18B'—C18'—H18C'	109.5
C19'—C16'—C18'	108.5 (2)	C16'—C19'—H19A'	109.5
C17'—C16'—C18'	107.0 (2)	C16'—C19'—H19B'	109.5
C19'—C16'—C13'	111.12 (18)	H19A'—C19'—H19B'	109.5
C17'—C16'—C13'	108.54 (16)	C16'—C19'—H19C'	109.5
C18'—C16'—C13'	111.77 (17)	H19A'—C19'—H19C'	109.5
C9—O1—H1	109.5	H19B'—C19'—H19C'	109.5
C9A—C1—C2—C3	1.9 (3)	C9A'—C1'—C2'—C3'	0.3 (3)
C1—C2—C3—C4	−2.0 (3)	C1'—C2'—C3'—C4'	0.4 (3)
C2—C3—C4—C4A	−0.7 (3)	C2'—C3'—C4'—C4A'	−0.5 (3)
C3—C4—C4A—C9A	3.6 (2)	C3'—C4'—C4A'—C9A'	0.0 (3)
C3—C4—C4A—C4B	−173.41 (17)	C3'—C4'—C4A'—C4B'	−178.88 (19)
C4—C4A—C4B—C5	3.4 (3)	C4'—C4A'—C4B'—C5'	1.0 (3)
C9A—C4A—C4B—C5	−173.92 (17)	C9A'—C4A'—C4B'—C5'	−178.01 (19)
C4—C4A—C4B—C8A	179.06 (17)	C4'—C4A'—C4B'—C8A'	178.92 (19)
C9A—C4A—C4B—C8A	1.79 (19)	C9A'—C4A'—C4B'—C8A'	−0.1 (2)
C8A—C4B—C5—C6	−1.2 (2)	C8A'—C4B'—C5'—C6'	1.8 (3)
C4A—C4B—C5—C6	174.09 (17)	C4A'—C4B'—C5'—C6'	179.59 (19)
C4B—C5—C6—C7	−0.5 (3)	C4B'—C5'—C6'—C7'	−1.6 (3)
C5—C6—C7—C8	1.7 (3)	C5'—C6'—C7'—C8'	0.3 (3)
C5—C4B—C8A—C8	1.9 (2)	C6'—C7'—C8'—C8A'	0.7 (3)
C4A—C4B—C8A—C8	−174.38 (15)	C7'—C8'—C8A'—C4B'	−0.4 (3)
C5—C4B—C8A—C9	179.94 (15)	C7'—C8'—C8A'—C9'	−175.81 (17)
C4A—C4B—C8A—C9	3.65 (19)	C5'—C4B'—C8A'—C8'	−0.9 (3)
C4B—C8A—C8—C7	−0.8 (3)	C4A'—C4B'—C8A'—C8'	−179.10 (16)
C9—C8A—C8—C7	−178.44 (16)	C5'—C4B'—C8A'—C9'	175.28 (16)
C6—C7—C8—C8A	−1.0 (3)	C4A'—C4B'—C8A'—C9'	−2.93 (19)
C8—C8A—C9—O1	49.7 (2)	C2'—C1'—C9A'—C4A'	−0.8 (3)
C4B—C8A—C9—O1	−128.14 (15)	C2'—C1'—C9A'—C9'	175.27 (17)
C8—C8A—C9—C10	−70.8 (2)	C4'—C4A'—C9A'—C1'	0.6 (3)
C4B—C8A—C9—C10	111.33 (16)	C4B'—C4A'—C9A'—C1'	179.74 (16)
C8—C8A—C9—C9A	170.85 (17)	C4'—C4A'—C9A'—C9'	−176.07 (16)
C4B—C8A—C9—C9A	−7.02 (17)	C4B'—C4A'—C9A'—C9'	3.0 (2)
C2—C1—C9A—C4A	1.0 (3)	C8'—C8A'—C9'—O1'	65.1 (2)
C2—C1—C9A—C9	−178.63 (16)	C4B'—C8A'—C9'—O1'	−110.77 (16)
C4—C4A—C9A—C1	−3.8 (2)	C8'—C8A'—C9'—C10'	−56.3 (2)
C4B—C4A—C9A—C1	173.80 (15)	C4B'—C8A'—C9'—C10'	127.87 (16)
C4—C4A—C9A—C9	175.92 (15)	C8'—C8A'—C9'—C9A'	−179.74 (18)
C4B—C4A—C9A—C9	−6.46 (18)	C4B'—C8A'—C9'—C9A'	4.43 (18)
O1—C9—C9A—C1	−51.9 (2)	C1'—C9A'—C9'—O1'	−69.2 (2)
C8A—C9—C9A—C1	−172.18 (17)	C4A'—C9A'—C9'—O1'	107.16 (16)
C10—C9—C9A—C1	68.8 (2)	C1'—C9A'—C9'—C10'	56.5 (2)
O1—C9—C9A—C4A	128.44 (15)	C4A'—C9A'—C9'—C10'	−127.18 (16)
C8A—C9—C9A—C4A	8.12 (17)	C1'—C9A'—C9'—C8A'	179.18 (17)
C10—C9—C9A—C4A	−110.91 (15)	C4A'—C9A'—C9'—C8A'	−4.48 (18)
O1—C9—C10—C11	3.9 (2)	C8A'—C9'—C10'—C15'	−74.2 (2)
C8A—C9—C10—C11	127.33 (18)	C9A'—C9'—C10'—C15'	41.4 (2)
C9A—C9—C10—C11	−120.28 (18)	O1'—C9'—C10'—C11'	−14.2 (2)
O1—C9—C10—C15	−176.62 (16)	C8A'—C9'—C10'—C11'	104.51 (19)
C8A—C9—C10—C15	−53.2 (2)	C9A'—C9'—C10'—C11'	−139.92 (17)
C9A—C9—C10—C15	59.2 (2)	O1'—C9'—C10'—C15'	167.05 (15)
C15—C10—C11—C12	0.4 (3)	C15'—C10'—C11'—C12'	−0.5 (3)
C9—C10—C11—C12	179.85 (16)	C9'—C10'—C11'—C12'	−179.30 (17)
C10—C11—C12—C13	0.0 (3)	C10'—C11'—C12'—C13'	0.3 (3)
C11—C12—C13—C14	−0.5 (3)	C11'—C12'—C13'—C14'	−0.2 (3)
C11—C12—C13—C16	178.64 (17)	C11'—C12'—C13'—C16'	−179.05 (18)
C12—C13—C14—C15	0.6 (3)	C12'—C13'—C14'—C15'	0.4 (3)
C16—C13—C14—C15	−178.56 (17)	C16'—C13'—C14'—C15'	179.18 (17)
C13—C14—C15—C10	−0.2 (3)	C11'—C10'—C15'—C14'	0.6 (3)
C11—C10—C15—C14	−0.3 (3)	C9'—C10'—C15'—C14'	179.40 (17)
C9—C10—C15—C14	−179.76 (17)	C13'—C14'—C15'—C10'	−0.6 (3)
C12—C13—C16—C17	127.56 (19)	C12'—C13'—C16'—C19'	−138.4 (2)
C14—C13—C16—C17	−53.3 (2)	C14'—C13'—C16'—C19'	42.8 (3)
C12—C13—C16—C19	6.3 (2)	C12'—C13'—C16'—C17'	100.7 (2)
C14—C13—C16—C19	−174.56 (17)	C14'—C13'—C16'—C17'	−78.1 (2)
C12—C13—C16—C18	−113.0 (2)	C12'—C13'—C16'—C18'	−17.1 (3)
C14—C13—C16—C18	66.1 (2)	C14'—C13'—C16'—C18'	164.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1′^i—H1′^i···O1	0.82	2.02	2.8276 (17)	167
O1—H1···C4^ii	0.82	2.40	3.175 (2)	159

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+2.