(2RS)-5,6:7,8-Dibenzobi­cyclo­[2.2.2]­octan-2-ol

The racemic form of the title secondary monoalcohol, C₁₆H₁₄O, forms crystals in which the mol­ecules are linked into chains by hydrogen bonding. The chain architecture is unusual; adjacent mol­ecules are related pseudosymmetrically, by either a pseudo-diad or a pseudo-glide plane, while alternate mol­ecules are related exactly by a crystallographic glide plane.

S1. Comment

Our interest in the modes of hydrogen bonding adopted by polycyclic monoalcohols (Morris et al., 2001, 2002) has led us to determine the crystal structure of the racemic form of the secondary alcohol (I) (Fig. 1 and Table 1). Monoalcohols in general show a preference for trigonal and tetragonal space groups, and their crystal structures frequently contain more than one crystallographically independent molecule (i.e. Z' > 1) (Brock & Duncan, 1994). These preferences are thought to arise from steric constraints in forming hydrogen bonds. Consistently with this view, we have recently shown (Fraile et al., 2003) that tertiary monoalcohols display these preferences in a particularly pronounced fashion.

The polycyclic and sterically hindered secondary alcohol (I) crystallizes in the non-centrosymmetric but non-chiral space group Pca2₁ (No. 29) with Z' equal to 2. Chains of molecules running parallel to the short c axis are linked by conventional hydrogen bonds (Table 2 and Fig. 2). In itself, this is not an unusual arrangement in homomolecular monoalcohol crystal structures (Brock & Duncan, 1994). However, the translationally repeated unit of the chain, consisting of four molecules related by an exact c-glide normal to a and by additional pseudosymmetry, is unusual and merits discussion.

The asymmetric unit we have chosen contains two enantiomeric molecules, and the coordinates of the atoms of molecule 2 are approximately related to those of the corresponding atoms of molecule 1 by the pseudosymmetric operation (x, 1/2 − y, 1/2 + z-δ); δ is 0.01–0.09 for individual C atoms, rising to 0.13 for the two O atoms, and its mean value is 0.038. If δ were 0 this operation would correspond exactly to that of a c-glide plane normal to the b axis, and the space group would become Iba2 (No. 45). The pseudosymmetry causes the hkl reflections to be systematically weak when h+k+l = 2n+1, this pseudo-absence being especially pronounced for the hk0 zone.

In each chain, the unit repeated by translation comprises four molecules linked by ···H—O1ⁱ···H—O2ⁱ···H—O1···H—O2··· hydrogen bonds; the symmetry operation (i), (3/2 − x, y, z − 1/2), defines a c-glide normal to a, and the molecule containing O1 is related to that containing O2 and O2ⁱ by pseudo-operations approximating respectively to a c-glide normal to b (see above) and to a diad axis parallel to c (3/2 − x, 1/2 − y, z-δ). Thus the chain sequence is ···RSSR··· where R and S indicate the configuration at Cn02 (n = 1 or 2) in successive molecules. The hydrogen bonds in each chain therefore connect pairs of molecules which may be of the same, or of opposite, chiralities.

The tendency for monoalcohols to crystallize with two or more molecules in the asymmetric unit is well established, and this feature of the structure of (I) is therefore not surprising. However, in their survey of hydrogen-bonding motifs adopted by monoalcohols, Brock & Duncan (1994) found only five out of 55 structures in which four molecules make up the translational repeat unit. Of these, only one, namely ethanol, resembles (I) in generating the chain by application of a glide operation to two independent molecules. However, the two independent ethanol molecules are not pseudosymmetrically related (Jonsson, 1976).

The two crystallographically independent molecules of (II) are structurally nearly identical. A least-squares fit of the positions of corresponding C or O atoms gives an r.m.s. Δ of 0.057 Å, with the O atoms showing the largest individual discrepancy [0.174 (5) Å]. Furthermore, for bond lengths and angles, the r.m.s. Δ values are respectively 0.011 Å and 1.1° (PLATON; Spek, 2003). Table 1 lists only the distances and angles in the CH(OH)—CH bridging units where the differences between the two molecules are greatest. Though complicated by minor disorder of the O atoms (see below), these differences are probably a consequence of the differing orientations of the OH bonds [Cn01—Cn02—On—H = −85 (4) and 8(4)° for n = 1 and 2, respectively]. This result illustrates the factors that cause sterically hindered alcohols to crystallize with Z' greater than 1; a pseudosymmetric relationship between molecules 1 and 2 permits differing hydrogen-bond orientations, which would be precluded if 1 and 2 were related exactly by space-group symmetry. Each molecule contains two C₈ units (defined by an aromatic ring plus the two C atoms directly attached to it), which are coplanar to within 0.05 Å and which define dihedral angles of 53.4 (1) and 52.8 (1)°. The mean C_ar—C_ar and C_ar—C_sp3 bond lengths are 1.391 and 1.516 Å, and their respective ranges are 1.380 (6)–1.405 (5) and 1.508 (4)–1.526 (4) Å. The atomic U^ij values are moderately well reproduced by a TLS analysis [Schomacher & Trueblood, 1968; R2 = (ΣΔU²/ΣU²)^1/2 = 0.16 and 0.14 for individual molecules]. The worst discrepancy in the Hirshfeld (1976) rigid-bond test is the value of ΔU for C202—C203 [0.008(2₄) Ų].

S2. Experimental

The title compound was first synthesized by Wawzonek and Hallum (1953). Our sample was provided by Professor Marie-Joséphe Brienne, Collége de France, Paris.

S3. Refinement

The absolute structure has not been determined experimentally. Our coordinates and drawings arbitrarily show S and R configurations at C102 and C202, respectively. All H atoms appeared in difference syntheses in stereochemically acceptable positions. In the final calculations, hydroxyl H atoms were freely refined. The other H atoms were placed in positions calculated using the HFIX option in SHELXL97 (Sheldrick, 1997) and then refined riding on their parent C atoms, with C—H distances of 1.00, 0.99 and 0.95 Å, respectively, for methine, methylene and aromatic C atoms and U_iso(H) values of 1.2U_eq(C). At a late stage in the analysis (R1 = 0.068 for observed data, wR2 = 0.180 for all data) two peaks of 0.8 e Å⁻³ with coordinates derived from those of O1 and O2 by inversion through the origin were found in the difference map. Accordingly, O1 and O2 have been disordered over two sites with occupancies α and 1-α [α = 0.856 (8)] after refinement. This disordered model led to significantly lower agreement indices and a featureless difference synthesis. There is no indication that disorder affects any of the C atoms.

Computing details

Data collection: COLLECT (Nonius, 1997–2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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: WinGX publication routines (Farrugia, 1999).

Figures

	Fig. 1. A view of the two independent molecules of (I), showing displacement ellipsoids at the 20% probability level. Here and in Fig. 2 dotted lines represent O—H···O hydrogen bonds. For clarity, the minor disorder sites of the two O atoms are not shown.
	Fig. 2. One of the hydrogen-bonded chains, viewed down the c axis. The a axis runs from left to right, and the b axis points upwards in the plane of the drawing.
	Fig. 3. A hydrogen-bonded chain, viewed down the a axis. The c axis points upwards, and the b axis runs horizontally from left to right. H atoms not involved in hydrogen bonding have been omitted. [Symmetry code: (i) 3/2 − x,y,1/2 + z.]

(I)

Crystal data

C16H14O	F(000) = 944
Mr = 222.27	Dx = 1.271 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2967 reflections
a = 14.3719 (3) Å	θ = 2.9–27.5°
b = 22.8650 (6) Å	µ = 0.08 mm^−1
c = 7.0703 (1) Å	T = 100 K
V = 2323.40 (8) Å^3	Needle, colourless
Z = 8	0.40 × 0.17 × 0.12 mm

Data collection

Nonius KappaCCD area-detector diffractometer	Rint = 0.057
CCD; rotation images; thick slices scans	θmax = 27.5°, θmin = 3°
17231 measured reflections	h = 0→18
2863 independent reflections	k = 0→29
2385 reflections with I > 2σ(I)	l = 0→9

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + 1.24P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.141	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.34 e Å^−3
2863 reflections	Δρmin = −0.24 e Å^−3
324 parameters

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C101	0.6182 (2)	0.14290 (12)	0.1204 (5)	0.0250 (7)
H101	0.6572	0.156	0.0113	0.03*
C102	0.6522 (2)	0.16967 (13)	0.3125 (6)	0.0325 (8)
H102	0.7145	0.1527	0.3432	0.039*
C103	0.5841 (2)	0.15254 (14)	0.4695 (5)	0.0317 (7)
H13A	0.5504	0.1877	0.5143	0.038*
H13B	0.6188	0.1358	0.5778	0.038*
C104	0.5136 (2)	0.10697 (12)	0.3938 (4)	0.0254 (7)
H104	0.4717	0.0921	0.496	0.03*
C105	0.4597 (2)	0.13735 (12)	0.2384 (5)	0.0234 (6)
C106	0.5165 (2)	0.15814 (11)	0.0936 (5)	0.0232 (7)
C107	0.6258 (2)	0.07728 (12)	0.1547 (5)	0.0224 (6)
C108	0.57027 (18)	0.05830 (12)	0.3051 (4)	0.0206 (6)
C109	0.3645 (2)	0.14696 (13)	0.2329 (5)	0.0283 (7)
H109	0.3256	0.132	0.3302	0.034*
C110	0.3265 (2)	0.17840 (13)	0.0850 (6)	0.0327 (8)
H110	0.2613	0.1851	0.0812	0.039*
C111	0.3826 (2)	0.20023 (13)	−0.0580 (5)	0.0335 (8)
H111	0.3559	0.2219	−0.1589	0.04*
C112	0.4784 (2)	0.19034 (12)	−0.0534 (5)	0.0307 (7)
H112	0.5172	0.2056	−0.1503	0.037*
C113	0.6846 (2)	0.03828 (13)	0.0640 (5)	0.0282 (7)
H113	0.7226	0.0509	−0.038	0.034*
C114	0.6872 (2)	−0.02004 (13)	0.1246 (5)	0.0298 (7)
H114	0.7277	−0.0471	0.0641	0.036*
C115	0.6310 (2)	−0.03854 (13)	0.2728 (5)	0.0286 (7)
H115	0.633	−0.0782	0.3123	0.034*
C116	0.5721 (2)	0.00041 (12)	0.3633 (5)	0.0260 (7)
H116	0.5335	−0.0124	0.4641	0.031*
O1	0.65976 (19)	0.23177 (10)	0.3135 (5)	0.0256 (8)	0.856 (8)
H1	0.715 (4)	0.2364 (19)	0.266 (9)	0.077 (18)*
O1'	0.6631 (17)	0.2341 (10)	0.185 (5)	0.056 (7)*	0.144 (8)
C201	0.6178 (2)	0.36156 (12)	0.5562 (5)	0.0260 (7)
H201	0.6508	0.3532	0.4347	0.031*
C202	0.6625 (2)	0.32924 (13)	0.7232 (5)	0.0299 (8)
H202	0.7272	0.3443	0.7404	0.036*
C203	0.6065 (2)	0.34264 (14)	0.9035 (5)	0.0327 (8)
H23A	0.6485	0.3591	1.0009	0.039*
H23B	0.5796	0.306	0.9539	0.039*
C204	0.5267 (2)	0.38716 (12)	0.8610 (5)	0.0267 (7)
H204	0.4905	0.3975	0.977	0.032*
C205	0.4665 (2)	0.35950 (12)	0.7108 (5)	0.0252 (7)
C206	0.5165 (2)	0.34405 (12)	0.5475 (5)	0.0248 (7)
C207	0.62434 (19)	0.42600 (12)	0.6105 (5)	0.0250 (7)
C208	0.57468 (19)	0.43973 (13)	0.7747 (5)	0.0242 (7)
C209	0.3721 (2)	0.34676 (13)	0.7225 (6)	0.0299 (7)
H209	0.3374	0.3579	0.8311	0.036*
C210	0.3292 (2)	0.31781 (13)	0.5750 (6)	0.0314 (8)
H210	0.2645	0.3095	0.5822	0.038*
C211	0.3792 (2)	0.30053 (12)	0.4157 (5)	0.0323 (8)
H211	0.349	0.2797	0.3169	0.039*
C212	0.4734 (2)	0.31383 (12)	0.4018 (5)	0.0312 (8)
H212	0.5079	0.3023	0.2935	0.037*
C213	0.6769 (2)	0.46819 (14)	0.5184 (6)	0.0333 (8)
H213	0.7107	0.4588	0.4071	0.04*
C214	0.6789 (2)	0.52472 (13)	0.5927 (6)	0.0362 (9)
H214	0.7156	0.5539	0.5324	0.043*
C215	0.6286 (2)	0.53890 (13)	0.7524 (6)	0.0345 (9)
H215	0.6299	0.5778	0.7996	0.041*
C216	0.5758 (2)	0.49640 (13)	0.8452 (5)	0.0302 (7)
H216	0.5411	0.5061	0.9552	0.036*
O2	0.66724 (18)	0.26707 (10)	0.6876 (4)	0.0243 (8)	0.856 (8)
H2	0.651 (4)	0.259 (2)	0.572 (10)	0.10 (2)*
O2'	0.6604 (16)	0.2697 (11)	0.820 (5)	0.078 (8)*	0.144 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C101	0.0205 (14)	0.0201 (14)	0.0343 (18)	−0.0032 (11)	0.0081 (13)	0.0014 (13)
C102	0.0210 (14)	0.0214 (15)	0.055 (2)	0.0000 (12)	−0.0082 (15)	−0.0050 (15)
C103	0.0372 (17)	0.0274 (15)	0.0305 (18)	0.0012 (14)	−0.0086 (15)	−0.0047 (13)
C104	0.0277 (15)	0.0266 (14)	0.0218 (16)	−0.0013 (12)	0.0001 (13)	−0.0037 (12)
C105	0.0246 (14)	0.0166 (13)	0.0291 (17)	−0.0007 (11)	0.0034 (13)	−0.0043 (12)
C106	0.0231 (14)	0.0154 (12)	0.0311 (18)	−0.0019 (11)	−0.0018 (13)	−0.0021 (12)
C107	0.0186 (13)	0.0192 (13)	0.0294 (17)	−0.0040 (11)	−0.0014 (12)	−0.0007 (12)
C108	0.0162 (13)	0.0237 (13)	0.0220 (15)	−0.0015 (11)	−0.0017 (11)	−0.0007 (12)
C109	0.0257 (15)	0.0239 (15)	0.0353 (18)	0.0003 (12)	0.0029 (14)	−0.0075 (14)
C110	0.0267 (15)	0.0240 (14)	0.048 (2)	0.0053 (13)	−0.0090 (16)	−0.0112 (15)
C111	0.0430 (19)	0.0186 (14)	0.039 (2)	0.0062 (13)	−0.0144 (16)	−0.0032 (14)
C112	0.0394 (18)	0.0214 (14)	0.0314 (19)	0.0009 (13)	0.0022 (15)	−0.0002 (13)
C113	0.0244 (14)	0.0268 (15)	0.0333 (19)	−0.0009 (12)	0.0055 (14)	−0.0016 (13)
C114	0.0275 (15)	0.0211 (14)	0.041 (2)	0.0021 (12)	−0.0018 (15)	−0.0065 (13)
C115	0.0265 (15)	0.0185 (13)	0.041 (2)	−0.0018 (12)	−0.0100 (14)	0.0022 (13)
C116	0.0252 (14)	0.0235 (14)	0.0293 (17)	−0.0053 (12)	−0.0055 (13)	0.0046 (13)
O1	0.0241 (14)	0.0178 (12)	0.035 (2)	−0.0044 (10)	0.0041 (11)	−0.0050 (11)
C201	0.0223 (15)	0.0213 (14)	0.0346 (18)	0.0020 (11)	0.0018 (13)	−0.0042 (13)
C202	0.0249 (15)	0.0213 (14)	0.043 (2)	0.0003 (12)	−0.0066 (15)	−0.0032 (14)
C203	0.0402 (18)	0.0240 (14)	0.0338 (19)	−0.0067 (14)	−0.0135 (16)	0.0038 (13)
C204	0.0288 (15)	0.0244 (14)	0.0268 (18)	−0.0031 (12)	−0.0018 (14)	−0.0028 (12)
C205	0.0260 (15)	0.0156 (13)	0.0341 (19)	0.0002 (11)	−0.0037 (14)	0.0028 (12)
C206	0.0242 (15)	0.0164 (12)	0.0337 (19)	0.0050 (11)	−0.0015 (13)	−0.0002 (13)
C207	0.0171 (13)	0.0220 (13)	0.0359 (19)	0.0039 (11)	−0.0002 (13)	−0.0024 (13)
C208	0.0171 (13)	0.0215 (14)	0.0341 (19)	0.0020 (11)	−0.0026 (12)	−0.0006 (12)
C209	0.0254 (15)	0.0249 (15)	0.0393 (19)	−0.0008 (12)	0.0043 (15)	0.0041 (14)
C210	0.0222 (15)	0.0251 (14)	0.047 (2)	−0.0055 (12)	−0.0067 (15)	0.0081 (15)
C211	0.0383 (18)	0.0186 (13)	0.040 (2)	−0.0036 (13)	−0.0130 (15)	0.0001 (14)
C212	0.0343 (17)	0.0196 (13)	0.040 (2)	0.0034 (13)	−0.0040 (15)	−0.0038 (13)
C213	0.0220 (15)	0.0312 (16)	0.047 (2)	0.0000 (13)	0.0044 (15)	0.0033 (15)
C214	0.0271 (16)	0.0227 (14)	0.059 (3)	−0.0017 (13)	−0.0008 (17)	0.0064 (16)
C215	0.0266 (16)	0.0162 (13)	0.061 (3)	0.0034 (12)	−0.0109 (16)	−0.0032 (15)
C216	0.0245 (15)	0.0236 (14)	0.042 (2)	0.0057 (12)	−0.0048 (15)	−0.0065 (14)
O2	0.0284 (14)	0.0182 (12)	0.0263 (18)	0.0050 (10)	−0.0063 (11)	−0.0051 (10)

Geometric parameters (Å, º)

C101—C106	1.514 (4)	C201—C206	1.511 (4)
C101—C107	1.524 (4)	C201—C207	1.526 (4)
C101—C102	1.568 (5)	C201—C202	1.533 (5)
C101—H101	1	C201—H201	1
C102—O1	1.424 (4)	C202—O2	1.445 (4)
C102—C103	1.531 (5)	C202—C203	1.538 (5)
C102—H102	1	C202—H202	1
C103—C104	1.548 (4)	C203—C204	1.564 (4)
C103—H13A	0.99	C203—H23A	0.99
C103—H13B	0.99	C203—H23B	0.99
C104—C105	1.513 (4)	C204—C205	1.508 (4)
C104—C108	1.515 (4)	C204—C208	1.514 (4)
C104—H104	1	C204—H204	1
C105—C109	1.387 (4)	C205—C209	1.390 (4)
C105—C106	1.392 (4)	C205—C206	1.405 (5)
C106—C112	1.386 (5)	C206—C212	1.386 (5)
C107—C113	1.386 (4)	C207—C213	1.387 (4)
C107—C108	1.398 (4)	C207—C208	1.398 (4)
C108—C116	1.386 (4)	C208—C216	1.389 (4)
C109—C110	1.381 (5)	C209—C210	1.381 (5)
C109—H109	0.95	C209—H209	0.95
C110—C111	1.386 (5)	C210—C211	1.393 (5)
C110—H110	0.95	C210—H210	0.95
C111—C112	1.396 (5)	C211—C212	1.392 (5)
C111—H111	0.95	C211—H211	0.95
C112—H112	0.95	C212—H212	0.95
C113—C114	1.401 (4)	C213—C214	1.395 (4)
C113—H113	0.95	C213—H213	0.95
C114—C115	1.389 (5)	C214—C215	1.380 (6)
C114—H114	0.95	C214—H214	0.95
C115—C116	1.385 (4)	C215—C216	1.397 (5)
C115—H115	0.95	C215—H215	0.95
C116—H116	0.95	C216—H216	0.95
O1—H1	0.87 (5)	O2—H2	0.87 (7)
O1'—H1	0.95 (5)
C106—C101—C107	108.4 (2)	C206—C201—C207	109.0 (2)
C106—C101—C102	108.6 (2)	C206—C201—C202	107.9 (3)
C107—C101—C102	103.0 (3)	C207—C201—C202	104.2 (3)
C106—C101—H101	112.1	C206—C201—H201	111.8
C107—C101—H101	112.1	C207—C201—H201	111.8
C102—C101—H101	112.1	C202—C201—H201	111.8
O1—C102—C103	107.5 (3)	O2—C202—C201	111.1 (3)
O1—C102—C101	114.7 (3)	O2—C202—C203	111.4 (3)
C103—C102—C101	109.2 (2)	C201—C202—C203	108.9 (2)
O1—C102—H102	108.4	O2—C202—H202	108.5
C103—C102—H102	108.4	C201—C202—H202	108.5
C101—C102—H102	108.4	C203—C202—H202	108.5
C102—C103—C104	109.8 (3)	C202—C203—C204	110.7 (3)
C102—C103—H13A	109.7	C202—C203—H23A	109.5
C104—C103—H13A	109.7	C204—C203—H23A	109.5
C102—C103—H13B	109.7	C202—C203—H23B	109.5
C104—C103—H13B	109.7	C204—C203—H23B	109.5
H13A—C103—H13B	108.2	H23A—C203—H23B	108.1
C105—C104—C108	108.2 (2)	C205—C204—C208	108.1 (3)
C105—C104—C103	106.1 (2)	C205—C204—C203	106.5 (2)
C108—C104—C103	106.6 (2)	C208—C204—C203	105.0 (2)
C105—C104—H104	111.9	C205—C204—H204	112.3
C108—C104—H104	111.9	C208—C204—H204	112.3
C103—C104—H104	111.9	C203—C204—H204	112.3
C109—C105—C106	120.2 (3)	C209—C205—C206	119.7 (3)
C109—C105—C104	126.8 (3)	C209—C205—C204	127.2 (3)
C106—C105—C104	113.0 (3)	C206—C205—C204	113.0 (3)
C112—C106—C105	120.1 (3)	C212—C206—C205	120.5 (3)
C112—C106—C101	126.7 (3)	C212—C206—C201	126.3 (3)
C105—C106—C101	113.3 (3)	C205—C206—C201	113.1 (3)
C113—C107—C108	120.0 (3)	C213—C207—C208	120.8 (3)
C113—C107—C101	127.1 (3)	C213—C207—C201	125.9 (3)
C108—C107—C101	112.7 (3)	C208—C207—C201	113.2 (3)
C116—C108—C107	120.7 (3)	C216—C208—C207	120.1 (3)
C116—C108—C104	126.1 (3)	C216—C208—C204	127.0 (3)
C107—C108—C104	113.2 (2)	C207—C208—C204	112.9 (3)
C110—C109—C105	119.6 (3)	C210—C209—C205	119.4 (3)
C110—C109—H109	120.2	C210—C209—H209	120.3
C105—C109—H109	120.2	C205—C209—H209	120.3
C109—C110—C111	120.6 (3)	C209—C210—C211	121.1 (3)
C109—C110—H110	119.7	C209—C210—H210	119.5
C111—C110—H110	119.7	C211—C210—H210	119.5
C110—C111—C112	119.9 (3)	C212—C211—C210	119.8 (3)
C110—C111—H111	120	C212—C211—H211	120.1
C112—C111—H111	120	C210—C211—H211	120.1
C106—C112—C111	119.5 (3)	C206—C212—C211	119.4 (3)
C106—C112—H112	120.2	C206—C212—H212	120.3
C111—C112—H112	120.2	C211—C212—H212	120.3
C107—C113—C114	119.2 (3)	C207—C213—C214	118.6 (3)
C107—C113—H113	120.4	C207—C213—H213	120.7
C114—C113—H113	120.4	C214—C213—H213	120.7
C115—C114—C113	120.3 (3)	C215—C214—C213	121.0 (3)
C115—C114—H114	119.8	C215—C214—H214	119.5
C113—C114—H114	119.8	C213—C214—H214	119.5
C116—C115—C114	120.5 (3)	C214—C215—C216	120.4 (3)
C116—C115—H115	119.7	C214—C215—H215	119.8
C114—C115—H115	119.7	C216—C215—H215	119.8
C115—C116—C108	119.2 (3)	C208—C216—C215	119.1 (3)
C115—C116—H116	120.4	C208—C216—H216	120.4
C108—C116—H116	120.4	C215—C216—H216	120.4
C102—O1—H1	101 (3)	C202—O2—H2	111 (4)
C106—C101—C102—O1	−70.4 (3)	C206—C201—C202—O2	68.0 (3)
C107—C101—C102—O1	174.8 (3)	C207—C201—C202—O2	−176.2 (2)
C106—C101—C102—C103	50.2 (3)	C206—C201—C202—C203	−55.0 (3)
C107—C101—C102—C103	−64.6 (3)	C207—C201—C202—C203	60.7 (3)
O1—C102—C103—C104	133.8 (3)	O2—C202—C203—C204	−126.0 (3)
C101—C102—C103—C104	8.8 (3)	C201—C202—C203—C204	−3.2 (3)
C102—C103—C104—C105	−63.0 (3)	C202—C203—C204—C205	58.6 (3)
C102—C103—C104—C108	52.1 (3)	C202—C203—C204—C208	−55.9 (3)
C108—C104—C105—C109	126.1 (3)	C208—C204—C205—C209	−126.3 (3)
C103—C104—C105—C109	−119.8 (3)	C203—C204—C205—C209	121.3 (3)
C108—C104—C105—C106	−55.9 (3)	C208—C204—C205—C206	56.3 (3)
C103—C104—C105—C106	58.2 (3)	C203—C204—C205—C206	−56.1 (3)
C109—C105—C106—C112	2.3 (4)	C209—C205—C206—C212	−3.0 (4)
C104—C105—C106—C112	−175.8 (3)	C204—C205—C206—C212	174.7 (3)
C109—C105—C106—C101	−179.0 (3)	C209—C205—C206—C201	179.3 (3)
C104—C105—C106—C101	2.9 (3)	C204—C205—C206—C201	−3.0 (3)
C107—C101—C106—C112	−129.3 (3)	C207—C201—C206—C212	131.3 (3)
C102—C101—C106—C112	119.5 (3)	C202—C201—C206—C212	−116.1 (3)
C107—C101—C106—C105	52.1 (3)	C207—C201—C206—C205	−51.1 (3)
C102—C101—C106—C105	−59.1 (3)	C202—C201—C206—C205	61.5 (3)
C106—C101—C107—C113	130.2 (3)	C206—C201—C207—C213	−130.6 (3)
C102—C101—C107—C113	−114.8 (3)	C202—C201—C207—C213	114.4 (3)
C106—C101—C107—C108	−54.7 (3)	C206—C201—C207—C208	52.7 (4)
C102—C101—C107—C108	60.2 (3)	C202—C201—C207—C208	−62.3 (3)
C113—C107—C108—C116	−1.0 (4)	C213—C207—C208—C216	1.4 (4)
C101—C107—C108—C116	−176.5 (3)	C201—C207—C208—C216	178.3 (3)
C113—C107—C108—C104	177.3 (3)	C213—C207—C208—C204	−176.4 (3)
C101—C107—C108—C104	1.9 (4)	C201—C207—C208—C204	0.5 (4)
C105—C104—C108—C116	−128.7 (3)	C205—C204—C208—C216	127.7 (3)
C103—C104—C108—C116	117.6 (3)	C203—C204—C208—C216	−119.0 (3)
C105—C104—C108—C107	53.0 (3)	C205—C204—C208—C207	−54.7 (3)
C103—C104—C108—C107	−60.7 (3)	C203—C204—C208—C207	58.7 (3)
C106—C105—C109—C110	−1.4 (4)	C206—C205—C209—C210	1.5 (4)
C104—C105—C109—C110	176.4 (3)	C204—C205—C209—C210	−175.8 (3)
C105—C109—C110—C111	0.2 (5)	C205—C209—C210—C211	0.8 (5)
C109—C110—C111—C112	0.2 (5)	C209—C210—C211—C212	−1.7 (5)
C105—C106—C112—C111	−1.9 (4)	C205—C206—C212—C211	2.1 (4)
C101—C106—C112—C111	179.6 (3)	C201—C206—C212—C211	179.5 (3)
C110—C111—C112—C106	0.7 (5)	C210—C211—C212—C206	0.2 (4)
C108—C107—C113—C114	0.2 (5)	C208—C207—C213—C214	−0.2 (5)
C101—C107—C113—C114	175.0 (3)	C201—C207—C213—C214	−176.6 (3)
C107—C113—C114—C115	0.5 (5)	C207—C213—C214—C215	−1.2 (5)
C113—C114—C115—C116	−0.4 (5)	C213—C214—C215—C216	1.3 (5)
C114—C115—C116—C108	−0.4 (5)	C207—C208—C216—C215	−1.3 (4)
C107—C108—C116—C115	1.1 (4)	C204—C208—C216—C215	176.2 (3)
C104—C108—C116—C115	−177.0 (3)	C214—C215—C216—C208	0.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.87 (5)	1.91 (5)	2.761 (4)	165 (4)
O2—H2···O1	0.87 (7)	1.94 (7)	2.768 (4)	159 (5)

Symmetry code: (i) −x+3/2, y, z−1/2.