The low-temperature phase transition of 9-methylfluoren-9-ol: comparison of the crystal structures at 100 and 200 K

Crystals of 9-methyl­fluoren-9-ol, C₁₄H₁₂O, undergo a reversible phase transition at 176 (2) K. The structure of the high-temperature α form at 200 K is compared with that of the low-temperature β form at 100 K. Both polymorphs crystallize in space group P with Z = 4 and contain discrete hydrogen-bonded R(8) ring tetramers arranged around crystallographic inversion centres. The most obvious changes observed on cooling the crystals to below 176 K are an abrupt increase of ca 0.5 Å in the shortest lattice translation, and a thermal transition with ΔH = 1 kJ mol⁻¹.

S1. Comment

Our interest in derivatives of fluoren-9-one (Morris et al., 2000) and in the hydrogen-bonding patterns displayed by tertiary monoalcohols (Morris et al., 2001) led us to examine the crystal structure of 9-methylfluoren-9-ol, (I), at 100 K (Fig. 1). \sch

At room temperature, (I) crystallizes as a centrosymmetric cyclic tetramer in the space group P1 with Z = 4 (Csöregh et al., 1993, hereinafter CCW93). At 293 K, our sample of (I) gave cell dimensions virtually identical to those reported in CCW93. However, we found that the crystals frequently, though not invariably, shattered on cooling. Further crystallographic investigation established that (I) undergoes a reversible phase transition at ca 173–176 K. We compare here the crystal structures adopted by (I) at 100 K (the β form) and 200 K (the α form). The latter structure is, in essence, that described in CCW93 when allowance is made for the difference in temperature. Attempts to define the temperature of the phase transition crystallographically and by differential scanning calorimetry (DSC) are also described.

Cooling a crystal of (I) from ambient temperature to 100 K does not alter its space group. At 100 K, the triclinic unit cell again contains four molecules linked into a ring by cooperative hydrogen bonding. Indeed, the crystal structure of the β polymorph is very similar to that of the α form, as can be seen from a comparison of their packing diagrams (Fig. 2). This similarity is emphasized here in two ways, as follows.

Firstly, for the β form, the unit cell has been chosen so that its axes correspond to those of the reduced cell used here and in CCW93 for the α form. The cell used for the β form can be transformed by the matrix (100/101/0–10) to give the reduced cell a = 9.2540 (2), b = 11.3720 (3) and c = 11.4154 (4) Å, and α = 77.009 (1), β = 72.892 (1) and γ = 69.243 (1)°. In the following discussion, the a axis is therefore always the shortest lattice translation for each structure. When (I) is cooled to below 173 K, the a axis increases abruptly by ca 0.5 Å and the cell angle β by 13°. The changes in the other cell parameters are less dramatic and there is no obvious discontinuity in the plot of unit-cell volume with temperature. A comparison of the diffractometer orientation matrices at 200 and 100 K e stablishes that, in the indexing we have chosen for the α and β forms, the directions of the crystallographic b and c axes change by no more than 2° during the phase transition, whereas the change in magnitude of the a axis is accompanied by a change in direction of 12°.

Secondly, the same atom-numbering system is used for the independent molecules A and B in the two forms, so that corresponding atoms occupying similar positions in the respective unit cells have the same identifier (Fig. 2). This is possible because the positions and orientations of the molecules relative to the cell axes differ only slightly in the two forms. Indeed, the coordinates of the β form can be used successfully as a starting point for refining the α structure; this refinement correctly repositions the atoms of molecule B, but the new position of atom C1A must be found from a difference synthesis and the other atoms of molecule A have to be renumbered to correspond with the scheme shown in Fig. 1.

In the β form, the two independent molecules, A and B, are structurally nearly indistinguishable at 100 K; the r.m.s. difference is 0.019 Å when the C and O atoms of molecule A are fitted to the corresponding atoms of molecule B transformed by the inversion operation (i) [Table 1; symmetry code: (i) 1 - x, 1 - y, 1 - z]. Each molecule shows almost exact C_s symmetry; the non-crystallographic mirror plane passes through atoms C1, C14 and O1, and the midpoint of the C7—C8 bond. The central five-membered ring adopts a very shallow envelope conformation, with atom C1 at the flap and the OH moiety equatorial, as may be seen from the endocyclic torsion angles (Table 1). The six-membered rings in each molecule are planar to within 0.008 Å and bend away from atom C14, so as to define dihedral angles of 3.7 (1) and 4.3 (1)° with one another. The most obvious difference between the two molecules is in the orientation of the hydroxyl groups [C14—C1—O1—H1 175 (2) and 146 (2)° in molecules A and B, respectively]. Each molecule appears to vibrate as a rigid body, since the atomic U^ij values are tolerably well reproduced by a TLS analysis (Schomaker & Trueblood, 1968), with R₂ = (ΣΔU²/ΣU²)^1/2 = 0.068 and 0.066 for molecules A and B, respectively. The worst discrepancy in the Hirshfeld (1976) rigid bond test is ΔU = 0.003(1₂)Ų.

The molecules in the α form at 200 K are almost indistinguishable, both from one another (r.m.s. difference 0.036 Å) and from those in the β polymorph. The two most striking differences in molecular structure between the α and β forms (cf. Tables 1 and 3) are that, in the α form, firstly the central rings are flatter, particularly those of molecule A, where the largest endocyclic torsion angle is only 1.3 (1)°, and secondly, the hydroxyl groups in the two independent molecules are no longer oriented differently [C14—C1—O1—H1 - 170 (1) and -166 (1)°]. The U^ij values at 200 K are roughly double those for the α form at 100 K and do not pass the rigid bond test [worst ΔU 0.021 (2) Ų for C4A—C5A], though the R₂ values for the TLS fit are 0.075 and 0.049.

Bond lengths and angles in both α and β forms agree with standard values (Orpen et al., 1992) and require no discussion.

The α and β forms of (I) both contain hydrogen-bonded cyclic tetramers which belong to the graph set R₄⁴(8) (Etter, 1990). This is not surprising; half of the 45 C_sp3-C—OH tertiary monoalcohol crystal structures in the Cambridge Structural Database (Version?; Allen & Kennard, 1993) also contain this hydrogen-bond motif, and no other motif is as common for this class of compound (Morris & Muir, 2002). The individual molecules of (I) in the α and β forms have structures which can barely be distinguished from one another, the hydrogen bonds that connect them (Tables 2 and 4) involve nearly identical O···O distances and in both tetramers the four O atoms are exactly coplanar.

It follows that the two forms differ only in the disposition of the four molecules relative to the plane of the O atoms and in the packing of the tetrameric units. These differences are small enough not to be obvious when the packing diagrams (Fig. 2) are compared; they only become apparent when the orientations of the molecular mirror planes relative to the plane defined by atoms O1A, O1B, O1Aⁱ and O1Bⁱ are considered (Fig. 3). The hydroxyl-substituted C1 atoms lie on different sides of the plane of the four O atoms in the two forms. The relevant torsion angles in the α and β forms consequently differ in sign (cf. Tables 1 and 3); the largest difference in magnitude is 17° between corresponding C1A—O1A···O1B—C1B angles [71.0 (2) and -53.6 (2)°]. There are also significant differences between the O···O···O angles at O1A and O1B [86 and 94° in the β form, but 82 and 98° in the α form]. Evidently, the β and α forms of (I) contain similar but not identical cyclic tetramers. A simplified description of the β to α transition in terms of the conversion of (IIA) to (IIB) is shown in the Scheme.

Repeated unit-cell determinations at different temperatures using a 700 Series Cryostream Cooler (Oxford Cryosystems, 2000) indicated that the mean transition temperature is 174.5 K with a slight hysteresis; on cooling, the α form persists down to 173 K, and on heating it is established at 176 K. The same crystal specimen can sometimes be converted from the α to the β form and back again several times before suffering obvious damage. A DSC experiment indicated that there is a strong thermal transition on heating, starting at 174.2 K, peaking at 177.6 K and finishing at 181.2 K. The enthalpy change for the transition, ΔH, is 1.00 (1) kJ mol^-1. On the assumption of thermodynamic reversibility, the entropy change, ΔS, is 5.7 J K^-1 mol^-1, taking 176 K (the mean defined by the DSC peak and the crystallographic mean value) as the transition temperature. Finally, we note that the crystallographic transition temperature on heating (176 K) agrees to within 2 K with the DSC peak value. The transition, which is easily observed, could be used in the calibration of crystal cryostats.

S2. Experimental

9-Methylfluoren-9-ol was synthesized by reaction of methyl magnesium iodide with fluoren-9-one under nitrogen according to the method of Amyes et al. (1992). Recrystallization of the product from toluene gave white crystals of (I) [m.p. 446–447 K; literature values 447 K (Amyes et al., 1992) and 445–447 K (Stiles & Sisti, 1961)]. DSC experiments were performed on a Mettler Toledo DSC 821 e. The DSC trace is included in the supplementary data for this paper.

S3. Refinement

A riding model was used for all H atoms attached to C atoms, with C—H distances of 0.95 and 0.98 Å for C(aromatic)-H and C(methyl)-H, respectively. H atoms attached to O atoms were freely refined. A single orientation parameter was refined for each methyl group.

Computing details

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (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: PLATON (Spek, 1990, 1998) and WinGX.

Figures

	Fig. 1. A view of molecule B of the β form of (I) at 100 K, showing 50% probability displacement ellipsoids. The same numbering scheme is used for each molecule in each form. Drawings of both molecules in both forms have been deposited.
	Fig. 2. The unit-cell contents of (a) the β form of (I) at 100 K and (b) the α form of (I) at 200 K. In each case, the viewing direction is roughly normal to the plane of the four hydroxyl O atoms. Hydrogen bonds are shown as broken lines.
	Fig. 3. The orientation of the molecular mirror planes, defined by atoms C1, C14 and O1, relative to the plane of the four hydroxyl O atoms in (a) the β form of (I) at 100 K and (b) the α form of (I) at 200 K.

(100K) 9-methylfluoren-9-ol

Crystal data

C14H12O	Z = 4
Mr = 196.24	F(000) = 416
Triclinic, P1	Dx = 1.225 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2540 (2) Å	Cell parameters from 3212 reflections
b = 11.4154 (4) Å	θ = 1.0–27.5°
c = 11.8476 (4) Å	µ = 0.08 mm^−1
α = 89.198 (1)°	T = 100 K
β = 116.162 (1)°	Plate, colourless
γ = 107.108 (1)°	0.41 × 0.32 × 0.05 mm
V = 1063.82 (6) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	Rint = 0.051
ω scans, thick slices	θmax = 27.4°, θmin = 1.9°
10069 measured reflections	h = −11→10
4749 independent reflections	k = −13→14
3507 reflections with I > 2σ(I)	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 0.33P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.127	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.31 e Å^−3
4749 reflections	Δρmin = −0.30 e Å^−3
281 parameters

Special details

Geometry. Hydrogen positions have been calculated using lengths of 0.95 and 0.98 A for C(aromatic)-H and C(methyl)-H bonds, respectively. Angles involving H atoms are based on trigonal or tetrahedral coordination at the corresponding carbon atoms.

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.

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

	x	y	z	Uiso*/Ueq
O1A	0.41573 (14)	0.32575 (10)	0.52814 (10)	0.0222 (3)
H1A	0.426 (3)	0.395 (2)	0.572 (2)	0.060 (7)*
C1A	0.4624 (2)	0.23603 (14)	0.61140 (14)	0.0207 (3)
C2A	0.3671 (2)	0.20828 (13)	0.69137 (14)	0.0190 (3)
C3A	0.1945 (2)	0.16960 (15)	0.65181 (15)	0.0244 (4)
H3A	0.1166	0.1569	0.5641	0.029*
C4A	0.1361 (2)	0.14942 (16)	0.74321 (17)	0.0278 (4)
H4A	0.0175	0.1242	0.7175	0.033*
C5A	0.2498 (2)	0.16581 (16)	0.87121 (16)	0.0278 (4)
H5A	0.208	0.1505	0.9321	0.033*
C6A	0.4237 (2)	0.20425 (14)	0.91136 (15)	0.0234 (4)
H6A	0.5013	0.215	0.999	0.028*
C7A	0.4823 (2)	0.22680 (14)	0.82070 (15)	0.0201 (3)
C8A	0.6566 (2)	0.27391 (14)	0.83502 (15)	0.0215 (3)
C9A	0.6466 (2)	0.28172 (14)	0.71369 (15)	0.0222 (3)
C10A	0.7936 (2)	0.32503 (17)	0.69971 (18)	0.0306 (4)
H10A	0.7877	0.3301	0.6178	0.037*
C11A	0.9493 (2)	0.36069 (18)	0.80746 (19)	0.0360 (5)
H11A	1.0508	0.391	0.7991	0.043*
C12A	0.9589 (2)	0.35280 (17)	0.92713 (19)	0.0343 (4)
H12A	1.0671	0.3777	0.9997	0.041*
C13A	0.8126 (2)	0.30887 (15)	0.94268 (17)	0.0279 (4)
H13A	0.8195	0.303	1.0249	0.034*
C14A	0.4243 (2)	0.12093 (15)	0.52614 (16)	0.0278 (4)
H14A	0.3036	0.0928	0.4643	0.042*
H14B	0.4509	0.0554	0.578	0.042*
H14C	0.4937	0.1406	0.4812	0.042*
O1B	0.56222 (14)	0.44686 (10)	0.38456 (10)	0.0226 (3)
H1B	0.517 (3)	0.393 (2)	0.428 (2)	0.052 (6)*
C1B	0.54512 (19)	0.38072 (14)	0.27445 (14)	0.0188 (3)
C2B	0.6999 (2)	0.34112 (14)	0.30187 (14)	0.0192 (3)
C3B	0.8680 (2)	0.41373 (15)	0.35043 (15)	0.0243 (4)
H3B	0.9007	0.5002	0.3741	0.029*
C4B	0.9892 (2)	0.35778 (17)	0.36413 (16)	0.0275 (4)
H4B	1.1057	0.4063	0.3983	0.033*
C5B	0.9400 (2)	0.23113 (17)	0.32794 (15)	0.0271 (4)
H5B	1.0237	0.1943	0.3373	0.032*
C6B	0.7712 (2)	0.15769 (15)	0.27851 (15)	0.0230 (3)
H6B	0.7383	0.0714	0.2534	0.028*
C7B	0.65092 (19)	0.21358 (14)	0.26663 (14)	0.0188 (3)
C8B	0.46619 (19)	0.16093 (14)	0.22242 (14)	0.0186 (3)
C9B	0.40367 (19)	0.25655 (14)	0.23037 (14)	0.0186 (3)
C10B	0.2342 (2)	0.23169 (15)	0.20002 (14)	0.0219 (3)
H10B	0.1919	0.2965	0.206	0.026*
C11B	0.1268 (2)	0.10947 (16)	0.16042 (15)	0.0243 (4)
H11B	0.0102	0.0908	0.1397	0.029*
C12B	0.1883 (2)	0.01463 (15)	0.15092 (15)	0.0243 (4)
H12B	0.1131	−0.068	0.1232	0.029*
C13B	0.3587 (2)	0.03931 (14)	0.18158 (14)	0.0214 (3)
H13B	0.4007	−0.0255	0.1748	0.026*
C14B	0.5166 (2)	0.46634 (14)	0.17200 (15)	0.0229 (3)
H14D	0.4124	0.4858	0.1523	0.034*
H14E	0.5058	0.4252	0.0953	0.034*
H14F	0.6134	0.543	0.2027	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0363 (7)	0.0185 (6)	0.0208 (6)	0.0126 (5)	0.0184 (5)	0.0059 (4)
C1A	0.0322 (9)	0.0183 (7)	0.0200 (8)	0.0118 (7)	0.0168 (7)	0.0057 (6)
C2A	0.0298 (9)	0.0136 (7)	0.0196 (7)	0.0091 (6)	0.0151 (7)	0.0038 (6)
C3A	0.0307 (9)	0.0232 (8)	0.0197 (8)	0.0091 (7)	0.0118 (7)	0.0046 (6)
C4A	0.0285 (9)	0.0285 (9)	0.0329 (9)	0.0103 (7)	0.0190 (8)	0.0078 (7)
C5A	0.0387 (10)	0.0279 (9)	0.0276 (9)	0.0122 (8)	0.0236 (8)	0.0083 (7)
C6A	0.0356 (9)	0.0214 (8)	0.0188 (8)	0.0112 (7)	0.0159 (7)	0.0042 (6)
C7A	0.0296 (9)	0.0150 (7)	0.0206 (8)	0.0096 (6)	0.0142 (7)	0.0031 (6)
C8A	0.0309 (9)	0.0144 (7)	0.0242 (8)	0.0099 (7)	0.0153 (7)	0.0049 (6)
C9A	0.0323 (9)	0.0166 (8)	0.0262 (8)	0.0119 (7)	0.0183 (7)	0.0071 (6)
C10A	0.0366 (10)	0.0327 (10)	0.0361 (10)	0.0165 (8)	0.0252 (9)	0.0146 (8)
C11A	0.0302 (10)	0.0385 (11)	0.0479 (12)	0.0143 (8)	0.0236 (9)	0.0209 (9)
C12A	0.0281 (9)	0.0297 (9)	0.0396 (11)	0.0097 (8)	0.0107 (8)	0.0121 (8)
C13A	0.0323 (9)	0.0234 (9)	0.0277 (9)	0.0101 (7)	0.0128 (8)	0.0068 (7)
C14A	0.0473 (11)	0.0228 (8)	0.0236 (8)	0.0163 (8)	0.0220 (8)	0.0045 (7)
O1B	0.0343 (7)	0.0178 (6)	0.0223 (6)	0.0067 (5)	0.0196 (5)	0.0004 (5)
C1B	0.0264 (8)	0.0172 (7)	0.0168 (7)	0.0067 (6)	0.0134 (6)	0.0013 (6)
C2B	0.0258 (8)	0.0205 (8)	0.0147 (7)	0.0081 (7)	0.0118 (6)	0.0036 (6)
C3B	0.0275 (9)	0.0241 (8)	0.0216 (8)	0.0045 (7)	0.0137 (7)	0.0018 (7)
C4B	0.0235 (9)	0.0360 (10)	0.0242 (8)	0.0080 (7)	0.0130 (7)	0.0046 (7)
C5B	0.0302 (9)	0.0397 (10)	0.0215 (8)	0.0192 (8)	0.0157 (7)	0.0090 (7)
C6B	0.0314 (9)	0.0249 (8)	0.0189 (8)	0.0134 (7)	0.0139 (7)	0.0042 (6)
C7B	0.0264 (8)	0.0203 (8)	0.0139 (7)	0.0098 (7)	0.0113 (6)	0.0039 (6)
C8B	0.0251 (8)	0.0198 (8)	0.0136 (7)	0.0082 (6)	0.0106 (6)	0.0033 (6)
C9B	0.0261 (8)	0.0190 (7)	0.0144 (7)	0.0080 (6)	0.0120 (6)	0.0040 (6)
C10B	0.0279 (8)	0.0235 (8)	0.0193 (8)	0.0110 (7)	0.0135 (7)	0.0043 (6)
C11B	0.0240 (8)	0.0291 (9)	0.0200 (8)	0.0042 (7)	0.0128 (7)	0.0015 (7)
C12B	0.0303 (9)	0.0210 (8)	0.0189 (8)	0.0016 (7)	0.0130 (7)	0.0001 (6)
C13B	0.0320 (9)	0.0185 (8)	0.0176 (7)	0.0093 (7)	0.0138 (7)	0.0033 (6)
C14B	0.0330 (9)	0.0183 (8)	0.0238 (8)	0.0099 (7)	0.0175 (7)	0.0054 (6)

Geometric parameters (Å, º)

O1A—C1A	1.4369 (18)	O1B—C1B	1.4395 (17)
O1A—H1A	0.92 (3)	O1B—H1B	0.92 (2)
C1A—C9A	1.523 (2)	C1B—C9B	1.524 (2)
C1A—C14A	1.524 (2)	C1B—C2B	1.526 (2)
C1A—C2A	1.529 (2)	C1B—C14B	1.528 (2)
C2A—C3A	1.377 (2)	C2B—C3B	1.380 (2)
C2A—C7A	1.402 (2)	C2B—C7B	1.400 (2)
C3A—C4A	1.398 (2)	C3B—C4B	1.397 (2)
C3A—H3A	0.95	C3B—H3B	0.95
C4A—C5A	1.388 (2)	C4B—C5B	1.393 (2)
C4A—H4A	0.95	C4B—H4B	0.95
C5A—C6A	1.387 (2)	C5B—C6B	1.387 (2)
C5A—H5A	0.95	C5B—H5B	0.95
C6A—C7A	1.392 (2)	C6B—C7B	1.394 (2)
C6A—H6A	0.95	C6B—H6B	0.95
C7A—C8A	1.474 (2)	C7B—C8B	1.474 (2)
C8A—C13A	1.387 (2)	C8B—C13B	1.390 (2)
C8A—C9A	1.402 (2)	C8B—C9B	1.399 (2)
C9A—C10A	1.387 (2)	C9B—C10B	1.383 (2)
C10A—C11A	1.385 (3)	C10B—C11B	1.395 (2)
C10A—H10A	0.95	C10B—H10B	0.95
C11A—C12A	1.384 (3)	C11B—C12B	1.390 (2)
C11A—H11A	0.95	C11B—H11B	0.95
C12A—C13A	1.391 (3)	C12B—C13B	1.391 (2)
C12A—H12A	0.95	C12B—H12B	0.95
C13A—H13A	0.95	C13B—H13B	0.95
C14A—H14A	0.98	C14B—H14D	0.98
C14A—H14B	0.98	C14B—H14E	0.98
C14A—H14C	0.98	C14B—H14F	0.98
O1B—O1A—O1B^i	86.28 (4)	C1A—C14A—H14C	109.5
O1B—O1A—C1A	129.38 (9)	H14A—C14A—H14C	109.5
O1B^i—O1A—C1A	122.15 (8)	H14B—C14A—H14C	109.5
O1A—O1B—O1A^i	93.72 (5)	C1B—O1B—H1B	110.2 (14)
O1A^i—O1B—C1B	140.87 (9)	O1B—C1B—C9B	112.63 (12)
O1A—O1B—C1B	120.13 (9)	O1B—C1B—C2B	112.47 (12)
C1A—O1A—H1A	110.9 (15)	C9B—C1B—C2B	101.57 (12)
O1A—C1A—C9A	113.21 (12)	O1B—C1B—C14B	106.72 (12)
O1A—C1A—C14A	105.90 (12)	C9B—C1B—C14B	112.32 (12)
C9A—C1A—C14A	112.28 (13)	C2B—C1B—C14B	111.24 (12)
O1A—C1A—C2A	112.42 (12)	C3B—C2B—C7B	120.82 (15)
C9A—C1A—C2A	101.52 (12)	C3B—C2B—C1B	128.56 (14)
C14A—C1A—C2A	111.70 (13)	C7B—C2B—C1B	110.59 (13)
C3A—C2A—C7A	120.75 (14)	C2B—C3B—C4B	118.82 (16)
C3A—C2A—C1A	128.88 (14)	C2B—C3B—H3B	120.6
C7A—C2A—C1A	110.37 (14)	C4B—C3B—H3B	120.6
C2A—C3A—C4A	118.71 (15)	C5B—C4B—C3B	120.24 (16)
C2A—C3A—H3A	120.6	C5B—C4B—H4B	119.9
C4A—C3A—H3A	120.6	C3B—C4B—H4B	119.9
C5A—C4A—C3A	120.62 (16)	C6B—C5B—C4B	121.25 (16)
C5A—C4A—H4A	119.7	C6B—C5B—H5B	119.4
C3A—C4A—H4A	119.7	C4B—C5B—H5B	119.4
C6A—C5A—C4A	120.82 (15)	C5B—C6B—C7B	118.33 (15)
C6A—C5A—H5A	119.6	C5B—C6B—H6B	120.8
C4A—C5A—H5A	119.6	C7B—C6B—H6B	120.8
C5A—C6A—C7A	118.65 (15)	C6B—C7B—C2B	120.53 (15)
C5A—C6A—H6A	120.7	C6B—C7B—C8B	131.09 (14)
C7A—C6A—H6A	120.7	C2B—C7B—C8B	108.38 (13)
C6A—C7A—C2A	120.42 (15)	C13B—C8B—C9B	120.71 (14)
C6A—C7A—C8A	130.74 (15)	C13B—C8B—C7B	130.62 (14)
C2A—C7A—C8A	108.81 (13)	C9B—C8B—C7B	108.63 (13)
C13A—C8A—C9A	120.87 (15)	C10B—C9B—C8B	120.65 (14)
C13A—C8A—C7A	130.91 (15)	C10B—C9B—C1B	128.79 (14)
C9A—C8A—C7A	108.21 (14)	C8B—C9B—C1B	110.56 (13)
C10A—C9A—C8A	120.23 (16)	C9B—C10B—C11B	118.62 (15)
C10A—C9A—C1A	128.83 (15)	C9B—C10B—H10B	120.7
C8A—C9A—C1A	110.93 (14)	C11B—C10B—H10B	120.7
C11A—C10A—C9A	118.77 (17)	C12B—C11B—C10B	120.78 (15)
C11A—C10A—H10A	120.6	C12B—C11B—H11B	119.6
C9A—C10A—H10A	120.6	C10B—C11B—H11B	119.6
C12A—C11A—C10A	120.93 (17)	C11B—C12B—C13B	120.74 (15)
C12A—C11A—H11A	119.5	C11B—C12B—H12B	119.6
C10A—C11A—H11A	119.5	C13B—C12B—H12B	119.6
C11A—C12A—C13A	120.99 (17)	C8B—C13B—C12B	118.50 (15)
C11A—C12A—H12A	119.5	C8B—C13B—H13B	120.8
C13A—C12A—H12A	119.5	C12B—C13B—H13B	120.8
C8A—C13A—C12A	118.21 (16)	C1B—C14B—H14D	109.5
C8A—C13A—H13A	120.9	C1B—C14B—H14E	109.5
C12A—C13A—H13A	120.9	H14D—C14B—H14E	109.5
C1A—C14A—H14A	109.5	C1B—C14B—H14F	109.5
C1A—C14A—H14B	109.5	H14D—C14B—H14F	109.5
H14A—C14A—H14B	109.5	H14E—C14B—H14F	109.5
C1A—O1A—O1B—C1B	71.0 (2)	C1A^i—O1A^i—O1B—C1B	16.0 (2)
C1A—O1A—O1B—O1A^i	−129.5 (1)	O1B^i—O1A—O1B—C1B	−159.5 (1)
C1A—O1A—O1B^i—O1A^i	135.3 (1)	O1B^i—O1A^i—O1B—C1B	151.3 (1)
O1B—O1A—C1A—C14A	−67.9 (2)	O1A—O1B—C1B—C14B	139.9 (1)
O1B^i—O1A—C1A—C14A	177.5 (1)	O1A^i—O1B—C1B—C14B	−6.4 (2)
C9A—C1A—C2A—C7A	−4.0 (2)	C9B—C1B—C2B—C7B	5.1 (2)
C1A—C2A—C7A—C8A	3.3 (2)	C1B—C2B—C7B—C8B	−3.5 (2)
C6A—C7A—C8A—C13A	0.3 (3)	C2B—C7B—C8B—C9B	0.3 (2)
C2A—C7A—C8A—C9A	−1.1 (2)	C7B—C8B—C9B—C1B	3.1 (2)
C7A—C8A—C9A—C1A	−1.6 (2)	C2B—C1B—C9B—C8B	−4.9 (2)
C2A—C1A—C9A—C8A	3.4 (2)	O1B—C1B—C9B—C8B	−125.40 (14)
O1A—C1A—C2A—C3A	55.1 (2)	O1B—C1B—C2B—C3B	−56.2 (2)
C9A—C1A—C2A—C3A	176.4 (2)	C9B—C1B—C2B—C3B	−176.89 (15)
C14A—C1A—C2A—C3A	−63.7 (2)	C14B—C1B—C2B—C3B	63.4 (2)
O1A—C1A—C2A—C7A	−125.3 (1)	O1B—C1B—C2B—C7B	125.70 (13)
C14A—C1A—C2A—C7A	115.9 (2)	C14B—C1B—C2B—C7B	−114.65 (14)
C7A—C2A—C3A—C4A	0.2 (2)	C7B—C2B—C3B—C4B	−0.1 (2)
C1A—C2A—C3A—C4A	179.7 (2)	C1B—C2B—C3B—C4B	−177.98 (15)
C2A—C3A—C4A—C5A	−1.2 (3)	C2B—C3B—C4B—C5B	0.7 (2)
C3A—C4A—C5A—C6A	0.9 (3)	C3B—C4B—C5B—C6B	−0.4 (2)
C4A—C5A—C6A—C7A	0.4 (2)	C4B—C5B—C6B—C7B	−0.5 (2)
C5A—C6A—C7A—C2A	−1.4 (2)	C5B—C6B—C7B—C2B	1.1 (2)
C5A—C6A—C7A—C8A	176.39 (15)	C5B—C6B—C7B—C8B	−177.70 (15)
C3A—C2A—C7A—C6A	1.1 (2)	C3B—C2B—C7B—C6B	−0.8 (2)
C1A—C2A—C7A—C6A	−178.51 (13)	C1B—C2B—C7B—C6B	177.43 (13)
C3A—C2A—C7A—C8A	−177.08 (14)	C3B—C2B—C7B—C8B	178.24 (14)
C2A—C7A—C8A—C13A	178.28 (16)	C6B—C7B—C8B—C13B	1.2 (3)
C6A—C7A—C8A—C9A	−179.01 (15)	C2B—C7B—C8B—C13B	−177.69 (15)
C13A—C8A—C9A—C10A	−0.1 (2)	C6B—C7B—C8B—C9B	179.19 (15)
C7A—C8A—C9A—C10A	179.29 (14)	C13B—C8B—C9B—C10B	1.2 (2)
C13A—C8A—C9A—C1A	178.97 (14)	C7B—C8B—C9B—C10B	−176.99 (13)
O1A—C1A—C9A—C10A	−56.9 (2)	C13B—C8B—C9B—C1B	−178.71 (13)
C14A—C1A—C9A—C10A	62.9 (2)	O1B—C1B—C9B—C10B	54.7 (2)
C2A—C1A—C9A—C10A	−177.65 (16)	C2B—C1B—C9B—C10B	175.21 (15)
O1A—C1A—C9A—C8A	124.06 (14)	C14B—C1B—C9B—C10B	−65.9 (2)
C14A—C1A—C9A—C8A	−116.08 (15)	C14B—C1B—C9B—C8B	114.06 (14)
C8A—C9A—C10A—C11A	−0.3 (2)	C8B—C9B—C10B—C11B	−0.5 (2)
C1A—C9A—C10A—C11A	−179.24 (16)	C1B—C9B—C10B—C11B	179.43 (14)
C9A—C10A—C11A—C12A	0.4 (3)	C9B—C10B—C11B—C12B	−0.4 (2)
C10A—C11A—C12A—C13A	0.0 (3)	C10B—C11B—C12B—C13B	0.5 (2)
C9A—C8A—C13A—C12A	0.5 (2)	C9B—C8B—C13B—C12B	−1.1 (2)
C7A—C8A—C13A—C12A	−178.78 (16)	C7B—C8B—C13B—C12B	176.68 (14)
C11A—C12A—C13A—C8A	−0.4 (3)	C11B—C12B—C13B—C8B	0.3 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B^i	0.92 (3)	1.84 (3)	2.725 (2)	163 (2)
O1B—H1B···O1A	0.92 (2)	1.85 (2)	2.740 (2)	163 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

(200K) 9-methylfluoren-9-ol

Crystal data

C14H12O	Z = 4
Mr = 196.24	F(000) = 416
Triclinic, P1	Dx = 1.195 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7380 (2) Å	Cell parameters from 5786 reflections
b = 11.4571 (3) Å	θ = 1.0–30.0°
c = 11.7097 (4) Å	µ = 0.07 mm^−1
α = 90.952 (2)°	T = 200 K
β = 103.462 (1)°	Plate, colourless
γ = 106.225 (1)°	0.52 × 0.49 × 0.04 mm
V = 1090.47 (5) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	Rint = 0.021
ω scans, thick slices	θmax = 30.1°, θmin = 1.8°
11636 measured reflections	h = −12→11
6338 independent reflections	k = −16→16
4662 reflections with I > 2σ(I)	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.07P)^2 + 0.25P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.156	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.35 e Å^−3
6338 reflections	Δρmin = −0.21 e Å^−3
281 parameters

Special details

Geometry. Hydrogen positions have been calculated using lengths of 0.95 and 0.98 A for C(aromatic)-H and C(methyl)-H bonds, respectively. Angles involving H atoms are based on trigonal or tetrahedral coordination at the corresponding carbon atoms.

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.

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

	x	y	z	Uiso*/Ueq
O1A	0.60712 (14)	0.37270 (9)	0.57885 (8)	0.0427 (3)
H1A	0.567 (2)	0.4256 (19)	0.6140 (18)	0.067 (6)*
C1A	0.59017 (17)	0.26368 (12)	0.63992 (10)	0.0349 (3)
C2A	0.42116 (18)	0.21676 (13)	0.66419 (12)	0.0402 (3)
C3A	0.2705 (2)	0.18396 (18)	0.58360 (18)	0.0620 (5)
H3A	0.2633	0.1865	0.5015	0.074*
C4A	0.1302 (3)	0.1473 (2)	0.6247 (2)	0.0763 (6)
H4A	0.0255	0.1247	0.5702	0.092*
C5A	0.1397 (2)	0.14294 (17)	0.7434 (2)	0.0742 (7)
H5A	0.0413	0.1176	0.7695	0.089*
C6A	0.2928 (2)	0.17534 (15)	0.82701 (18)	0.0571 (5)
H6A	0.2993	0.1716	0.9089	0.069*
C7A	0.43400 (18)	0.21294 (11)	0.78542 (12)	0.0383 (3)
C8A	0.60837 (18)	0.25695 (11)	0.84717 (10)	0.0347 (3)
C9A	0.70132 (17)	0.28845 (11)	0.76405 (11)	0.0345 (3)
C10A	0.8705 (2)	0.33418 (15)	0.80031 (14)	0.0486 (4)
H10A	0.9349	0.3552	0.7445	0.058*
C11A	0.9449 (2)	0.34876 (17)	0.92150 (17)	0.0622 (5)
H11A	1.0611	0.3812	0.9479	0.075*
C12A	0.8532 (3)	0.31701 (17)	1.00259 (15)	0.0631 (5)
H12A	0.9063	0.3273	1.0843	0.076*
C13A	0.6856 (2)	0.27054 (14)	0.96668 (12)	0.0509 (4)
H13A	0.6225	0.2477	1.0231	0.061*
C14A	0.6302 (2)	0.17239 (14)	0.56417 (12)	0.0469 (4)
H14A	0.5498	0.1537	0.4876	0.07*
H14B	0.6259	0.0973	0.6038	0.07*
H14C	0.7408	0.2074	0.5524	0.07*
O1B	0.51128 (17)	0.44556 (10)	0.35899 (9)	0.0552 (3)
H1B	0.530 (2)	0.4066 (19)	0.4196 (19)	0.068 (6)*
C1B	0.5441 (2)	0.38851 (11)	0.26106 (10)	0.0389 (3)
C2B	0.70203 (18)	0.35180 (12)	0.29519 (10)	0.0375 (3)
C3B	0.8611 (2)	0.42323 (19)	0.34731 (14)	0.0642 (5)
H3B	0.8834	0.5078	0.3683	0.077*
C4B	0.9871 (2)	0.3687 (3)	0.36816 (16)	0.0823 (8)
H4B	1.0966	0.4164	0.4039	0.099*
C5B	0.9551 (2)	0.2465 (3)	0.33758 (15)	0.0755 (7)
H5B	1.0436	0.2114	0.3514	0.091*
C6B	0.7976 (2)	0.17341 (18)	0.28733 (13)	0.0520 (4)
H6B	0.7765	0.0887	0.2677	0.062*
C7B	0.67036 (17)	0.22773 (12)	0.26625 (10)	0.0337 (3)
C8B	0.49380 (16)	0.17472 (11)	0.21596 (10)	0.0314 (3)
C9B	0.41716 (17)	0.26655 (12)	0.21489 (10)	0.0346 (3)
C10B	0.2485 (2)	0.23922 (19)	0.17298 (14)	0.0553 (4)
H10B	0.1956	0.3013	0.1723	0.066*
C11B	0.1578 (2)	0.1201 (2)	0.13209 (16)	0.0708 (6)
H11B	0.0417	0.1004	0.1042	0.085*
C12B	0.2333 (2)	0.03017 (19)	0.13124 (16)	0.0653 (5)
H12B	0.169	−0.0508	0.1017	0.078*
C13B	0.4015 (2)	0.05584 (13)	0.17277 (13)	0.0487 (4)
H13B	0.4535	−0.0067	0.1719	0.058*
C14B	0.5490 (3)	0.47956 (14)	0.16731 (13)	0.0614 (5)
H14D	0.4432	0.4975	0.1454	0.092*
H14E	0.5699	0.4446	0.0976	0.092*
H14F	0.6369	0.555	0.1987	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0706 (7)	0.0431 (5)	0.0310 (4)	0.0335 (5)	0.0230 (4)	0.0154 (4)
C1A	0.0507 (8)	0.0367 (6)	0.0267 (5)	0.0235 (6)	0.0142 (5)	0.0095 (5)
C2A	0.0468 (8)	0.0367 (7)	0.0430 (7)	0.0218 (6)	0.0102 (6)	0.0091 (5)
C3A	0.0509 (10)	0.0695 (12)	0.0661 (11)	0.0254 (9)	0.0054 (8)	0.0157 (9)
C4A	0.0505 (11)	0.0763 (14)	0.1052 (17)	0.0248 (10)	0.0164 (11)	0.0272 (12)
C5A	0.0537 (11)	0.0518 (10)	0.138 (2)	0.0245 (8)	0.0512 (12)	0.0324 (11)
C6A	0.0694 (11)	0.0420 (8)	0.0842 (12)	0.0279 (8)	0.0501 (10)	0.0257 (8)
C7A	0.0528 (8)	0.0274 (6)	0.0480 (7)	0.0209 (5)	0.0262 (6)	0.0127 (5)
C8A	0.0562 (8)	0.0273 (5)	0.0294 (5)	0.0200 (5)	0.0179 (5)	0.0071 (4)
C9A	0.0485 (7)	0.0314 (6)	0.0310 (5)	0.0193 (5)	0.0147 (5)	0.0083 (4)
C10A	0.0500 (9)	0.0474 (8)	0.0521 (8)	0.0169 (7)	0.0154 (7)	0.0124 (7)
C11A	0.0585 (10)	0.0546 (10)	0.0598 (10)	0.0139 (8)	−0.0081 (8)	0.0010 (8)
C12A	0.0889 (14)	0.0586 (10)	0.0358 (7)	0.0258 (10)	−0.0012 (8)	−0.0016 (7)
C13A	0.0873 (12)	0.0460 (8)	0.0289 (6)	0.0312 (8)	0.0184 (7)	0.0064 (5)
C14A	0.0738 (10)	0.0455 (8)	0.0346 (6)	0.0332 (7)	0.0197 (7)	0.0056 (6)
O1B	0.1129 (10)	0.0467 (6)	0.0281 (5)	0.0521 (7)	0.0249 (5)	0.0091 (4)
C1B	0.0718 (9)	0.0290 (6)	0.0265 (5)	0.0261 (6)	0.0183 (6)	0.0066 (4)
C2B	0.0505 (8)	0.0370 (6)	0.0249 (5)	0.0088 (6)	0.0140 (5)	0.0029 (5)
C3B	0.0689 (12)	0.0673 (11)	0.0377 (8)	−0.0124 (9)	0.0172 (7)	−0.0074 (7)
C4B	0.0406 (10)	0.148 (2)	0.0411 (9)	0.0031 (12)	0.0083 (7)	−0.0027 (12)
C5B	0.0506 (10)	0.149 (2)	0.0382 (8)	0.0479 (13)	0.0100 (7)	0.0118 (11)
C6B	0.0599 (10)	0.0775 (11)	0.0361 (7)	0.0441 (9)	0.0161 (7)	0.0130 (7)
C7B	0.0450 (7)	0.0379 (6)	0.0251 (5)	0.0199 (5)	0.0124 (5)	0.0078 (4)
C8B	0.0439 (7)	0.0287 (5)	0.0270 (5)	0.0153 (5)	0.0132 (5)	0.0074 (4)
C9B	0.0469 (7)	0.0396 (6)	0.0260 (5)	0.0227 (6)	0.0134 (5)	0.0080 (5)
C10B	0.0519 (9)	0.0853 (13)	0.0426 (8)	0.0386 (9)	0.0154 (7)	0.0111 (8)
C11B	0.0424 (9)	0.1064 (17)	0.0522 (10)	0.0039 (10)	0.0116 (7)	0.0001 (10)
C12B	0.0648 (11)	0.0601 (11)	0.0545 (10)	−0.0107 (9)	0.0184 (8)	−0.0020 (8)
C13B	0.0690 (10)	0.0309 (6)	0.0465 (8)	0.0107 (7)	0.0193 (7)	0.0051 (6)
C14B	0.1293 (17)	0.0362 (7)	0.0347 (7)	0.0399 (9)	0.0310 (9)	0.0144 (6)

Geometric parameters (Å, º)

O1A—C1A	1.4384 (15)	C8B—C9B	1.3948 (17)
C1A—C2A	1.519 (2)	C9B—C10B	1.382 (2)
C1A—C9A	1.5204 (18)	C10B—C11B	1.384 (3)
C1A—C14A	1.5237 (18)	C11B—C12B	1.371 (3)
C2A—C3A	1.378 (2)	C12B—C13B	1.380 (3)
C2A—C7A	1.4001 (19)	O1A—H1A	0.91 (2)
C3A—C4A	1.380 (3)	C3A—H3A	0.9500
C4A—C5A	1.376 (3)	C4A—H4A	0.9500
C5A—C6A	1.409 (3)	C5A—H5A	0.9500
C6A—C7A	1.391 (2)	C6A—H6A	0.9500
C7A—C8A	1.464 (2)	C10A—H10A	0.9500
C8A—C13A	1.3901 (18)	C11A—H11A	0.9500
C8A—C9A	1.3976 (17)	C12A—H12A	0.9500
C9A—C10A	1.381 (2)	C13A—H13A	0.9500
C10A—C11A	1.402 (2)	C14A—H14A	0.9800
C11A—C12A	1.371 (3)	C14A—H14B	0.9800
C12A—C13A	1.369 (3)	C14A—H14C	0.9800
O1B—C1B	1.4342 (15)	O1B—H1B	0.85 (2)
C1B—C9B	1.518 (2)	C3B—H3B	0.9500
C1B—C2B	1.521 (2)	C4B—H4B	0.9500
C1B—C14B	1.5265 (17)	C5B—H5B	0.9500
C2B—C3B	1.388 (2)	C6B—H6B	0.9500
C2B—C7B	1.3901 (18)	C10B—H10B	0.9500
C3B—C4B	1.388 (3)	C11B—H11B	0.9500
C4B—C5B	1.373 (4)	C12B—H12B	0.9500
C5B—C6B	1.380 (3)	C13B—H13B	0.9500
C6B—C7B	1.3962 (19)	C14B—H14D	0.9800
C7B—C8B	1.4620 (19)	C14B—H14E	0.9800
C8B—C13B	1.3909 (19)	C14B—H14F	0.9800
O1B—O1A—O1B^i	81.83 (4)	C10B—C9B—C1B	129.62 (13)
O1B—O1A—C1A	140.35 (8)	C8B—C9B—C1B	110.29 (12)
O1B^i—O1A—C1A	120.89 (8)	C9B—C10B—C11B	119.09 (16)
O1A—O1B—O1A^i	98.17 (5)	C12B—C11B—C10B	120.91 (17)
O1A^i—O1B—C1B	143.02 (9)	C11B—C12B—C13B	120.76 (17)
O1A—O1B—C1B	118.67 (9)	C12B—C13B—C8B	118.92 (16)
O1A—C1A—C2A	112.15 (10)	C1A—O1A—H1A	109.3 (13)
O1A—C1A—C9A	111.66 (11)	C2A—C3A—H3A	120.7
C2A—C1A—C9A	101.58 (10)	C4A—C3A—H3A	120.7
O1A—C1A—C14A	106.01 (10)	C5A—C4A—H4A	119.5
C2A—C1A—C14A	113.34 (12)	C3A—C4A—H4A	119.5
C9A—C1A—C14A	112.29 (11)	C4A—C5A—H5A	119.4
C3A—C2A—C7A	121.47 (15)	C6A—C5A—H5A	119.4
C3A—C2A—C1A	127.75 (14)	C7A—C6A—H6A	121.1
C7A—C2A—C1A	110.75 (12)	C5A—C6A—H6A	121.1
C2A—C3A—C4A	118.56 (19)	C9A—C10A—H10A	120.8
C5A—C4A—C3A	121.0 (2)	C11A—C10A—H10A	120.8
C4A—C5A—C6A	121.17 (17)	C12A—C11A—H11A	119.4
C7A—C6A—C5A	117.70 (17)	C10A—C11A—H11A	119.4
C6A—C7A—C2A	120.07 (15)	C13A—C12A—H12A	119.8
C6A—C7A—C8A	131.58 (14)	C11A—C12A—H12A	119.8
C2A—C7A—C8A	108.32 (11)	C12A—C13A—H13A	120.2
C13A—C8A—C9A	120.26 (14)	C8A—C13A—H13A	120.2
C13A—C8A—C7A	130.93 (13)	C1A—C14A—H14A	109.5
C9A—C8A—C7A	108.81 (11)	C1A—C14A—H14B	109.5
C10A—C9A—C8A	120.14 (13)	H14A—C14A—H14B	109.5
C10A—C9A—C1A	129.34 (12)	C1A—C14A—H14C	109.5
C8A—C9A—C1A	110.52 (12)	H14A—C14A—H14C	109.5
C9A—C10A—C11A	118.39 (15)	H14B—C14A—H14C	109.5
C12A—C11A—C10A	121.20 (17)	C4B—C3B—H3B	120.6
C13A—C12A—C11A	120.46 (15)	C2B—C3B—H3B	120.6
C12A—C13A—C8A	119.55 (15)	C5B—C4B—H4B	119.7
O1B—C1B—C9B	112.47 (12)	C3B—C4B—H4B	119.7
O1B—C1B—C2B	112.53 (11)	C4B—C5B—H5B	119.2
C9B—C1B—C2B	101.69 (10)	C6B—C5B—H5B	119.2
O1B—C1B—C14B	106.07 (10)	C5B—C6B—H6B	121.0
C9B—C1B—C14B	111.94 (12)	C7B—C6B—H6B	121.0
C2B—C1B—C14B	112.31 (13)	C9B—C10B—H10B	120.5
C3B—C2B—C7B	120.22 (16)	C11B—C10B—H10B	120.5
C3B—C2B—C1B	129.36 (15)	C12B—C11B—H11B	119.5
C7B—C2B—C1B	110.42 (12)	C10B—C11B—H11B	119.5
C2B—C3B—C4B	118.75 (19)	C11B—C12B—H12B	119.6
C5B—C4B—C3B	120.64 (18)	C13B—C12B—H12B	119.6
C4B—C5B—C6B	121.60 (18)	C12B—C13B—H13B	120.5
C5B—C6B—C7B	118.01 (18)	C8B—C13B—H13B	120.5
C2B—C7B—C6B	120.76 (14)	C1B—C14B—H14D	109.5
C2B—C7B—C8B	108.75 (11)	C1B—C14B—H14E	109.5
C6B—C7B—C8B	130.49 (13)	H14D—C14B—H14E	109.5
C13B—C8B—C9B	120.24 (13)	C1B—C14B—H14F	109.5
C13B—C8B—C7B	131.01 (12)	H14D—C14B—H14F	109.5
C9B—C8B—C7B	108.75 (11)	H14E—C14B—H14F	109.5
C10B—C9B—C8B	120.07 (14)
C1A—O1A—O1B—C1B	−53.6 (2)	C1A^i—O1A^i—O1B—C1B	−30.0 (2)
C1A—O1A—O1B—O1A^i	129.8 (1)	O1B^i—O1A—O1B—C1B	176.7 (1)
C1A—O1A—O1B^i—O1A^i	−145.1 (1)	O1B^i—O1A^i—O1B—C1B	−175.1 (2)
O1B—O1A—C1A—C14A	48.9 (2)	O1A—O1B—C1B—C14B	−155.8 (1)
O1B^i—O1A—C1A—C14A	166.5 (1)	O1A^i—O1B—C1B—C14B	18.7 (2)
C9A—C1A—C2A—C7A	−1.0 (1)	C9B—C1B—C2B—C7B	3.0 (1)
C1A—C2A—C7A—C8A	0.4 (1)	C1B—C2B—C7B—C8B	−1.7 (1)
C6A—C7A—C8A—C13A	2.5 (2)	C2B—C7B—C8B—C9B	−0.4 (1)
C2A—C7A—C8A—C9A	0.5 (1)	C7B—C8B—C9B—C1B	2.4 (1)
C7A—C8A—C9A—C1A	−1.2 (1)	C2B—C1B—C9B—C8B	−3.2 (1)
C2A—C1A—C9A—C8A	1.3 (1)	O1B—C1B—C2B—C3B	−56.77 (18)
O1A—C1A—C2A—C3A	57.90 (19)	C9B—C1B—C2B—C3B	−177.33 (13)
C9A—C1A—C2A—C3A	177.24 (15)	C14B—C1B—C2B—C3B	62.85 (18)
C14A—C1A—C2A—C3A	−62.09 (18)	O1B—C1B—C2B—C7B	123.52 (12)
O1A—C1A—C2A—C7A	−120.36 (12)	C14B—C1B—C2B—C7B	−116.87 (13)
C14A—C1A—C2A—C7A	119.65 (12)	C7B—C2B—C3B—C4B	0.9 (2)
C7A—C2A—C3A—C4A	0.3 (3)	C1B—C2B—C3B—C4B	−178.80 (14)
C1A—C2A—C3A—C4A	−177.77 (16)	C2B—C3B—C4B—C5B	0.1 (3)
C2A—C3A—C4A—C5A	−0.2 (3)	C3B—C4B—C5B—C6B	−1.1 (3)
C3A—C4A—C5A—C6A	−0.2 (3)	C4B—C5B—C6B—C7B	1.0 (2)
C4A—C5A—C6A—C7A	0.6 (3)	C3B—C2B—C7B—C6B	−0.98 (19)
C5A—C6A—C7A—C2A	−0.5 (2)	C1B—C2B—C7B—C6B	178.77 (11)
C5A—C6A—C7A—C8A	177.05 (14)	C3B—C2B—C7B—C8B	178.53 (11)
C3A—C2A—C7A—C6A	0.1 (2)	C5B—C6B—C7B—C2B	0.0 (2)
C1A—C2A—C7A—C6A	178.44 (12)	C5B—C6B—C7B—C8B	−179.37 (13)
C3A—C2A—C7A—C8A	−178.01 (14)	C2B—C7B—C8B—C13B	179.34 (13)
C2A—C7A—C8A—C13A	−179.79 (13)	C6B—C7B—C8B—C13B	−1.2 (2)
C6A—C7A—C8A—C9A	−177.25 (13)	C6B—C7B—C8B—C9B	179.04 (13)
C13A—C8A—C9A—C10A	−0.50 (19)	C13B—C8B—C9B—C10B	1.29 (18)
C7A—C8A—C9A—C10A	179.24 (12)	C7B—C8B—C9B—C10B	−178.95 (11)
C13A—C8A—C9A—C1A	179.07 (11)	C13B—C8B—C9B—C1B	−177.40 (11)
O1A—C1A—C9A—C10A	−59.46 (17)	O1B—C1B—C9B—C10B	57.68 (17)
C2A—C1A—C9A—C10A	−179.15 (14)	C2B—C1B—C9B—C10B	178.28 (13)
C14A—C1A—C9A—C10A	59.45 (18)	C14B—C1B—C9B—C10B	−61.64 (18)
O1A—C1A—C9A—C8A	121.03 (11)	O1B—C1B—C9B—C8B	−123.80 (11)
C14A—C1A—C9A—C8A	−120.07 (13)	C14B—C1B—C9B—C8B	116.89 (13)
C8A—C9A—C10A—C11A	−0.5 (2)	C8B—C9B—C10B—C11B	−0.2 (2)
C1A—C9A—C10A—C11A	180.00 (14)	C1B—C9B—C10B—C11B	178.20 (14)
C9A—C10A—C11A—C12A	0.9 (3)	C9B—C10B—C11B—C12B	−0.9 (3)
C10A—C11A—C12A—C13A	−0.3 (3)	C10B—C11B—C12B—C13B	0.9 (3)
C11A—C12A—C13A—C8A	−0.7 (3)	C11B—C12B—C13B—C8B	0.2 (3)
C9A—C8A—C13A—C12A	1.1 (2)	C9B—C8B—C13B—C12B	−1.3 (2)
C7A—C8A—C13A—C12A	−178.54 (14)	C7B—C8B—C13B—C12B	179.03 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B^i	0.91 (2)	1.84 (2)	2.728 (1)	162 (2)
O1B—H1B···O1A	0.85 (2)	1.91 (2)	2.736 (1)	161 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.