Apparent shortening of the Csp³-Csp³ bond analysed via a variable-temperature X-ray diffraction study in racemic 1,1'-binaphthalene-2,2'-diyl diethyl bis­(carbonate)

Crystal structure determination at room temperature [292 (2) K] of racemic 1,1'-binaphthalene-2,2'-diyl diethyl bis(­carbonate), C₂₆H₂₂O₆, showed that one of the terminal carbon-carbon bond lengths is very short [Csp³-Csp³ = 1.327 (6) Å]. The reason for such a short bond length has been analysed by collecting data sets on the same crystal at 393, 150 and 90 K. The values of the corrected bond lengths clearly suggest that the shortening is mainly due to positional disorder at two sites, with minor perturbations arising as a result of thermal vibrations. The positional disorder has been resolved in the analysis of the 90 K data following the changes in the unit-cell parameters for the data sets at 150 and 90 K, which appear to be an artifact of a near centre of symmetry relationship between the two independent mol­ecules in the space group P at these temperatures. Indeed, the unit cell at low temperature (150 and 90 K) is a supercell of the room-temperature unit cell.

S1. Comment

The appearance of a short carbon–carbon bond is often encountered in crystal structure determinations and is explained either as a consequence of thermal effects or as a structural disorder of some kind; theoretical calculations support both these observations. In crystal structures, long and short bonds have been treated as a consequence of rotational oscillations of molecules in crystals, as proposed by Cruickshank (1956). Dunitz (1999) has observed that 'the discrepancy between the 'curiously short' carbon–carbon double bond distance in 3-ethynylcyclopropene, as measured experimentally by X-ray analysis [1.255 (2) Å], compared with the value derived from high level ab initio calculations (ca 1.28 Å), is largely due to neglect of corrections for molecular motion in the crystal'. It was suggested that THMA (thermal motion analysis) clearly brings out the importance of thermal corrections between the X-ray distances and theoretically computed values (Dunitz, Maverick & Trueblood, 1988 and/or Dunitz, Shomaker & Trueblood, 1988; Dunitz, 1995). On the other hand, the shortening of the bond is explained as either due to ring strain (Xie & Schaffer, 1981 or????1989; Ermer & Lex, 1987) or owing to special electronic effects (Ermer et al., 1989; Allen, 1980,1981; Hagen et al., 1972; Traetteberg et al., 1984; Irngartinger et al., 1984). It has been argued that hybridization alone is not the cause for short C—C bonds, indeed symmetry and geometrical constraints play a significant role (Huntley et al., 2005). We have determined the crystal structure of racemic 1,1'-binaphthalene-2,2'-diyl diethyl biscarbonate, (I), at room temperature and have observed a very short Csp³—Csp³ bond length of 1.327 (6) Å in one of the terminal ethyl groups.

In this structure, there are no strains involved and no significant electronic effects in the molecule. One would expect that analysis of the structure determined at different temperatures (in this case at 393, 150 and 90 K) for the same crystal should reveal whether the shortening is due either entirely to thermal effects or to positional disorder. The bond length corrections due to thermal effects are applied based on the THMA (Dunitz, Maverick & Trueblood, 1988 and/or Dunitz, Shomaker & Trueblood, 1988; Dunitz, 1995) analysis before comparisons of variations in bond lengths. It is of interest to note that the unit cell at 150 K is a supercell of that observed at 292 K, and this feature, as shown in Fig. 1, explains the near doubling of the unit-cell volume observed at lower temperatures (150 and 90 K). The transformation matrix is (110, 101, 011).

At 292 K, the compound crystallizes in space group P1 with Z = 2. Fig. 2 shows the molecular structure with the atom numbering. All displacement ellipsoids are large and, in particular, those associated with the short-bond atoms C22 and C23 are very large. Thermal motion analysis using the program THMA (Dunitz, Maverick & Trueblood, 1988 and/or Dunitz, Shomaker & Trueblood, 1988; Dunitz, 1995) was used to obtain corrected bond lengths for all bonds; however, the C22—C23 bond continues to be exceptionally short [1.327 (6) Å]. From a search of the Cambridge Structural Database (Version 5.29 of 2008; Allen, 2002), this is one of a number of short single C—C bonds found in the literature for a molecule of this type, i.e. in which there is either no highly strained ring or no well known electronic effect due to conjugation. Fig. 3 is a packing diagram, with the orientation of the unit cell and hence its contents similar to that of the resulting supercell at low temperatures to ensure easy comparison. The packing in the lattice is mainly through weak interactions involving an intermolecular π–π [3.880 (2) Å] stacking interaction between the centroids of the C12–C17 rings at (x, y, z) and (-x + 2, -y, -z).

At 393 K, the cell parameters and the packing of the molecules in the unit cell are similar to those at room temperature. However, the displacement parameters of all atoms show the expected increase, and in particular those of both C22 and C23 are remarkably enhanced (Fig. 1S, supplementary material). It is noteworthy that the THMA analysis results in a C22–C23 bond length of 1.335 Å, suggesting that the bond shortening is certainly not only due to thermal effects.

The same crystal when cooled to 150 K indexes uniquely with Z = 4 and a cell volume almost double that of the 292K structure. It is noteworthy that the short C—C bond is now associated with only one molecule [THMA-corrected C22—C23=1.343 (4) Å], and the second molecule shows a closer to normal bond length [THMA-corrected C22'—C23' = 1.454 (3) Å]. Thus it appears that resolution of the overlap of molecules is beginning to take place at this temperature. The molecule is shown in Fig. 2S (supplmentary material), and details of the C—H···O hydorgen bonding are given in Table 1.

At 90 K, the cell volume contracts slightly compared with that at 150 K; however, the disorder at the C22—C23 site is now resolved. Fig. 5 shows the molecular structure of the compound, and the features of the positionally disordered C22 and C23 atoms now correspond to normal bond lengths [1.502 (5) Å none of the values in the CIF correspond to this]. The refinements suggest an occupancy ratio of 58:42 for the disordered atoms C22 and C22A, respectively. The refinements were carried out keeping the constraint on occupancy for C22 and C23 as one block and that for C22A and C23A as another block. The packing in the lattice (Fig. 4) is mainly through weak interactions involving intermolecular C—H···O contacts (Table 2) and π–π stacking interactions [with centroid–centroid distances of 3.849 (2) and 3.960 (1) Å, {for which rings?} with symmetry codes (-x + 1, -y +1, -z + 1) and (-x +1, -y +1, -z) ]. There are two types of C—H···π interactions [C3—H3···π and C3'—H3'···π, with H···π distances of 2.86 and 2.88 Å, {for which rings?} with symmetry operations (-x + 2, -y, -z + 1) and (-x + 1, -y +1, -z), respectively].

The formation of a terminal short bond withou the influence of strain or hybridization is of fundamental importance. The results clearly indicate that positional disorder could be the cause, and the structural analysis at different temperatures clearly brings out the salient features of such an effect. It is to be noted that thermal effects alone cannot resolve such unusual observed bond lengths. The unit cell at 150 K and below shows a supercell formation.

Related literature

For related literature, see: Allen (1980, 1981, 2002); Cruickshank (1956); Dunitz (1995, 1999); Dunitz, Maverick & Trueblood (1988); Dunitz, Shomaker & Trueblood (1988); Ermer & Lex (1987); Ermer et al. (1989); Hagen et al. (1972); Irngartinger et al. (1984); Kulkarni (2003); Traetteberg et al. (1984).

S2. Experimental

Racemic 1,1'-bi-2,2'-naphthol (2 g m, 6.9 mmol) was dissolved in dichloromethane (10 ml) under nitrogen atmosphere. Triethylamine (1.947 ml, 13.8 mmol) and ethyl chloroformate (1.334 ml, 13.8 mmol) were added, and the mixture was stirred for 30 min. The reaction mixture was washed with water and the solvent evaporated in vacuo to obtain the racemic 1,1'-binaphthalene-2,2'-diyl diethyl biscarbonate (2.39 g, 6.7 mmol, 99%; Kulkarni, 2003). ¹H NMR (300 MHz, CDCl3): δ 1.0 (3H, t), 3.9 (2H, q), 7.1–8.0 (12H, m). HR–MS: 453.1314 (M+Na), 315.1414, 431.1520 448.1765 [C₂₆H₂₂O₆ molecular Mass (M) = 430.1415]. The compound was crystallized from ethyl acetate by slow evaporation at room temperature, resulting in two different morphological forms, blocks and plates. The crystallographic data collected on crystals of both morphologies gave the same unit-cell parameters and same results, thus ruling out the possibility of concomitant polymorphs.

S3. Refinement

All non hydrogen atoms were refined anisotropically and the occupancy refinements with the 90 K data were done using the PART command in SHELXL97. All hydrogen atoms were positioned geometrically with fixed C–H distances in the range 0.93–0.97 Å and refined using the riding model with U_iso(H)= 1.2U_eq(Csp²) and 1.5U_eq(Csp³).

Computing details

For all compounds, data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Version 6.14; Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), POV-RAY (Persistence of Vision Team, 2004) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).

Figures

Figure 1: Diagram showing the supercell at 90 K, with unit-cell parameters defined as a', b', c', along with the subcell at 292 K, defined with cell parameters a, b, c, with respect to a common origin (0, 0, 0). Figure 2: The molecular structure at 292 K, with 30% probability displacement ellipsoids. Figure 3: The packing of the molecules at 292 K in the unit cell, shown in the same orientation as the resulting supercell at low temperature. Figure 4: The packing at low temperature, showing the molecules in the supercell. Figure 5: The molecular structure at 90 K, showing the atom labelling for all non-H atoms, with 50%probability displacement ellipsoids. Figure 1S: ORTEP diagram with 30% thermal ellipsoid probability at 393 K temperature. Figure 2S:ORTEP diagram with 50% thermal ellipsoid probability at 150 K temperature. Figure 3S: DSC plot for 1,1'-Bis-2,2'-naphthol biscarbonate (278 K/min) with the melting point at 417.34 K.

(292K) 1,1'-binaphthalene-2,2'-diyl diethyl bis(carbonate)

Crystal data

C26H22O6	Z = 2
Mr = 430.44	F(000) = 452
Triclinic, P1	Dx = 1.294 Mg m^−3
Hall symbol: -P 1	Melting point: 417.67 K
a = 9.7614 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0379 (14) Å	Cell parameters from 558 reflections
c = 12.3947 (17) Å	θ = 0.9–28.0°
α = 89.490 (2)°	µ = 0.09 mm^−1
β = 84.810 (2)°	T = 292 K
γ = 65.989 (2)°	Block, colourless
V = 1104.3 (3) Å^3	0.50 × 0.31 × 0.25 mm

Data collection

Bruker SMART CCD area detector diffractometer	4176 independent reflections
Radiation source: fine-focus sealed tube	2806 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ϕ and ω scans	θmax = 25.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.907, Tmax = 0.977	k = −12→12
11287 measured reflections	l = −15→15

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.191	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0996P)^2 + 0.1958P] where P = (Fo^2 + 2Fc^2)/3
4176 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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

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

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

	x	y	z	Uiso*/Ueq
C1	1.0259 (2)	0.2977 (2)	0.38275 (16)	0.0554 (5)
C2	1.0067 (3)	0.2070 (3)	0.46549 (17)	0.0684 (6)
H2	0.9434	0.1599	0.4576	0.082*
C3	1.0801 (3)	0.1880 (3)	0.5566 (2)	0.0893 (8)
H3	1.0657	0.1286	0.6105	0.107*
C4	1.1759 (3)	0.2560 (4)	0.5699 (3)	0.0987 (10)
H4	1.2257	0.2415	0.6323	0.118*
C5	1.1975 (3)	0.3431 (3)	0.4931 (3)	0.0897 (9)
H5	1.2621	0.3881	0.5032	0.108*
C6	1.1229 (2)	0.3671 (2)	0.3970 (2)	0.0678 (6)
C7	1.1414 (3)	0.4590 (3)	0.3149 (3)	0.0824 (8)
H7	1.2064	0.5043	0.3229	0.099*
C8	1.0667 (3)	0.4825 (3)	0.2252 (2)	0.0781 (7)
H8	1.0795	0.5438	0.1724	0.094*
C9	0.9699 (3)	0.4136 (2)	0.21267 (17)	0.0615 (5)
C10	0.9479 (2)	0.3220 (2)	0.28763 (15)	0.0539 (5)
C11	0.8536 (3)	0.2422 (2)	0.26830 (16)	0.0627 (6)
C12	0.9227 (4)	0.1030 (3)	0.21078 (19)	0.0835 (8)
C13	1.0751 (5)	0.0434 (3)	0.1689 (2)	0.1004 (10)
H13	1.1350	0.0936	0.1790	0.120*
C14	1.1354 (6)	−0.0878 (3)	0.1135 (3)	0.1424 (17)
H14	1.2360	−0.1269	0.0858	0.171*
C15	1.0460 (11)	−0.1627 (6)	0.0987 (5)	0.192 (4)
H15	1.0883	−0.2512	0.0599	0.230*
C16	0.9017 (9)	−0.1125 (6)	0.1381 (4)	0.167 (3)
H16	0.8457	−0.1665	0.1277	0.200*
C17	0.8333 (6)	0.0253 (4)	0.1966 (3)	0.1182 (14)
C18	0.6830 (7)	0.0816 (6)	0.2395 (4)	0.147 (2)
H18	0.6261	0.0280	0.2312	0.176*
C19	0.6170 (4)	0.2147 (5)	0.2940 (3)	0.1216 (14)
H19	0.5166	0.2515	0.3221	0.146*
C20	0.7060 (3)	0.2936 (3)	0.3062 (2)	0.0788 (7)
C21	0.5269 (3)	0.5350 (4)	0.3290 (2)	0.0897 (9)
C22	0.3675 (4)	0.7853 (6)	0.3700 (5)	0.1561 (18)
H22A	0.3376	0.7733	0.2995	0.187*
H22B	0.2816	0.8040	0.4229	0.187*
C23	0.4017 (6)	0.9005 (6)	0.3690 (7)	0.230 (4)
H23A	0.4183	0.9214	0.4409	0.345*
H23B	0.3201	0.9832	0.3439	0.345*
H23C	0.4915	0.8802	0.3213	0.345*
C24	0.7757 (3)	0.5487 (3)	0.10833 (17)	0.0656 (6)
C25	0.5867 (4)	0.6550 (4)	−0.0087 (3)	0.1133 (11)
H25A	0.5167	0.6803	0.0562	0.136*
H25B	0.5431	0.6212	−0.0640	0.136*
C26	0.6070 (5)	0.7833 (4)	−0.0454 (3)	0.1382 (15)
H26A	0.6442	0.8207	0.0109	0.207*
H26B	0.5123	0.8563	−0.0629	0.207*
H26C	0.6781	0.7582	−0.1086	0.207*
O1	0.64499 (18)	0.4264 (2)	0.36659 (13)	0.0844 (5)
O2	0.4691 (2)	0.5291 (3)	0.24982 (19)	0.1154 (8)
O3	0.4910 (2)	0.6486 (3)	0.39597 (18)	0.1068 (7)
O4	0.9022 (2)	0.42899 (16)	0.11537 (11)	0.0759 (5)
O5	0.71982 (19)	0.6436 (2)	0.17533 (14)	0.0841 (5)
O6	0.7267 (2)	0.5393 (2)	0.01436 (13)	0.0903 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0463 (10)	0.0558 (11)	0.0577 (11)	−0.0136 (9)	−0.0074 (9)	−0.0070 (9)
C2	0.0719 (14)	0.0765 (14)	0.0572 (12)	−0.0281 (12)	−0.0191 (10)	0.0066 (10)
C3	0.0922 (19)	0.0984 (19)	0.0635 (15)	−0.0203 (16)	−0.0299 (13)	0.0056 (13)
C4	0.0806 (19)	0.110 (2)	0.0832 (19)	−0.0094 (17)	−0.0398 (15)	−0.0162 (17)
C5	0.0547 (14)	0.0895 (18)	0.117 (2)	−0.0165 (13)	−0.0278 (14)	−0.0306 (17)
C6	0.0456 (11)	0.0625 (13)	0.0879 (16)	−0.0144 (10)	−0.0051 (10)	−0.0182 (12)
C7	0.0563 (13)	0.0702 (15)	0.123 (2)	−0.0301 (12)	0.0008 (14)	−0.0157 (15)
C8	0.0773 (16)	0.0609 (14)	0.0935 (18)	−0.0310 (12)	0.0195 (14)	−0.0006 (12)
C9	0.0703 (13)	0.0527 (11)	0.0558 (12)	−0.0209 (10)	0.0025 (10)	−0.0019 (9)
C10	0.0597 (12)	0.0518 (11)	0.0497 (11)	−0.0224 (9)	−0.0040 (9)	−0.0004 (8)
C11	0.0856 (16)	0.0722 (14)	0.0469 (11)	−0.0456 (12)	−0.0251 (10)	0.0182 (9)
C12	0.153 (3)	0.0653 (14)	0.0540 (13)	−0.0594 (17)	−0.0473 (15)	0.0240 (11)
C13	0.156 (3)	0.0589 (15)	0.0689 (16)	−0.0256 (17)	−0.0161 (18)	0.0030 (12)
C14	0.247 (5)	0.0606 (18)	0.086 (2)	−0.026 (2)	−0.025 (2)	−0.0018 (16)
C15	0.404 (11)	0.074 (3)	0.101 (3)	−0.087 (5)	−0.097 (5)	0.018 (2)
C16	0.352 (9)	0.099 (4)	0.115 (4)	−0.137 (5)	−0.135 (5)	0.051 (3)
C17	0.223 (4)	0.095 (2)	0.092 (2)	−0.106 (3)	−0.096 (3)	0.0478 (17)
C18	0.231 (5)	0.159 (4)	0.151 (4)	−0.160 (4)	−0.133 (4)	0.093 (3)
C19	0.132 (3)	0.172 (4)	0.125 (3)	−0.115 (3)	−0.075 (2)	0.078 (3)
C20	0.0931 (18)	0.108 (2)	0.0636 (14)	−0.0651 (17)	−0.0355 (13)	0.0300 (14)
C21	0.0590 (15)	0.143 (3)	0.0812 (18)	−0.0543 (17)	−0.0184 (14)	0.0344 (18)
C22	0.076 (2)	0.167 (4)	0.202 (5)	−0.021 (3)	−0.044 (3)	0.051 (4)
C23	0.125 (4)	0.120 (4)	0.415 (11)	−0.007 (3)	−0.081 (5)	−0.015 (5)
C24	0.0774 (15)	0.0726 (15)	0.0523 (12)	−0.0371 (13)	−0.0014 (11)	0.0011 (11)
C25	0.118 (3)	0.132 (3)	0.090 (2)	−0.046 (2)	−0.0384 (19)	0.003 (2)
C26	0.141 (3)	0.114 (3)	0.133 (3)	−0.016 (2)	−0.059 (3)	0.005 (2)
O1	0.0609 (10)	0.1310 (15)	0.0651 (10)	−0.0409 (10)	−0.0184 (8)	0.0198 (10)
O2	0.0984 (14)	0.161 (2)	0.1133 (15)	−0.0712 (15)	−0.0594 (13)	0.0460 (14)
O3	0.0681 (12)	0.1398 (19)	0.0970 (14)	−0.0256 (12)	−0.0139 (10)	0.0168 (14)
O4	0.1117 (13)	0.0584 (9)	0.0484 (8)	−0.0259 (9)	−0.0043 (8)	0.0049 (6)
O5	0.0699 (10)	0.0953 (12)	0.0727 (10)	−0.0180 (9)	−0.0106 (8)	−0.0172 (9)
O6	0.1201 (15)	0.0950 (13)	0.0563 (10)	−0.0421 (12)	−0.0189 (9)	0.0033 (8)

Geometric parameters (Å, º)

C1—C6	1.409 (3)	C16—C17	1.437 (7)
C1—C2	1.415 (3)	C16—H16	0.9300
C1—C10	1.427 (3)	C17—C18	1.394 (6)
C2—C3	1.363 (3)	C18—C19	1.376 (6)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.385 (4)	C19—C20	1.411 (4)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.346 (4)	C20—O1	1.408 (3)
C4—H4	0.9300	C21—O2	1.189 (3)
C5—C6	1.420 (4)	C21—O3	1.323 (4)
C5—H5	0.9300	C21—O1	1.342 (3)
C6—C7	1.416 (4)	C22—C23	1.327 (6)
C7—C8	1.351 (4)	C22—O3	1.468 (4)
C7—H7	0.9300	C22—H22A	0.9700
C8—C9	1.397 (3)	C22—H22B	0.9700
C8—H8	0.9300	C23—H23A	0.9600
C9—C10	1.366 (3)	C23—H23B	0.9600
C9—O4	1.405 (3)	C23—H23C	0.9600
C10—C11	1.480 (3)	C24—O5	1.185 (3)
C11—C20	1.357 (4)	C24—O6	1.317 (3)
C11—C12	1.442 (4)	C24—O4	1.337 (3)
C12—C13	1.408 (4)	C25—O6	1.439 (4)
C12—C17	1.409 (5)	C25—C26	1.445 (5)
C13—C14	1.366 (4)	C25—H25A	0.9700
C13—H13	0.9300	C25—H25B	0.9700
C14—C15	1.387 (9)	C26—H26A	0.9600
C14—H14	0.9300	C26—H26B	0.9600
C15—C16	1.333 (9)	C26—H26C	0.9600
C15—H15	0.9300
C6—C1—C2	118.28 (19)	C17—C16—H16	120.2
C6—C1—C10	119.9 (2)	C18—C17—C12	120.2 (4)
C2—C1—C10	121.81 (18)	C18—C17—C16	121.6 (5)
C3—C2—C1	120.7 (2)	C12—C17—C16	118.2 (5)
C3—C2—H2	119.7	C19—C18—C17	121.5 (3)
C1—C2—H2	119.7	C19—C18—H18	119.2
C2—C3—C4	120.7 (3)	C17—C18—H18	119.2
C2—C3—H3	119.6	C18—C19—C20	118.2 (4)
C4—C3—H3	119.6	C18—C19—H19	120.9
C5—C4—C3	120.5 (2)	C20—C19—H19	120.9
C5—C4—H4	119.7	C11—C20—O1	117.3 (2)
C3—C4—H4	119.7	C11—C20—C19	122.6 (3)
C4—C5—C6	120.9 (2)	O1—C20—C19	119.9 (3)
C4—C5—H5	119.5	O2—C21—O3	127.6 (3)
C6—C5—H5	119.5	O2—C21—O1	126.0 (4)
C1—C6—C7	118.5 (2)	O3—C21—O1	106.4 (2)
C1—C6—C5	118.9 (3)	C23—C22—O3	114.1 (4)
C7—C6—C5	122.6 (2)	C23—C22—H22A	108.7
C8—C7—C6	121.4 (2)	O3—C22—H22A	108.7
C8—C7—H7	119.3	C23—C22—H22B	108.7
C6—C7—H7	119.3	O3—C22—H22B	108.7
C7—C8—C9	119.4 (2)	H22A—C22—H22B	107.6
C7—C8—H8	120.3	C22—C23—H23A	109.5
C9—C8—H8	120.3	C22—C23—H23B	109.5
C10—C9—C8	122.6 (2)	H23A—C23—H23B	109.5
C10—C9—O4	118.20 (19)	C22—C23—H23C	109.5
C8—C9—O4	119.0 (2)	H23A—C23—H23C	109.5
C9—C10—C1	118.23 (19)	H23B—C23—H23C	109.5
C9—C10—C11	121.30 (18)	O5—C24—O6	127.5 (2)
C1—C10—C11	120.36 (17)	O5—C24—O4	125.5 (2)
C20—C11—C12	119.2 (2)	O6—C24—O4	107.0 (2)
C20—C11—C10	122.0 (2)	O6—C25—C26	111.9 (3)
C12—C11—C10	118.7 (2)	O6—C25—H25A	109.2
C13—C12—C17	119.6 (3)	C26—C25—H25A	109.2
C13—C12—C11	122.2 (2)	O6—C25—H25B	109.2
C17—C12—C11	118.2 (3)	C26—C25—H25B	109.2
C14—C13—C12	120.2 (4)	H25A—C25—H25B	107.9
C14—C13—H13	119.9	C25—C26—H26A	109.5
C12—C13—H13	119.9	C25—C26—H26B	109.5
C13—C14—C15	119.8 (5)	H26A—C26—H26B	109.5
C13—C14—H14	120.1	C25—C26—H26C	109.5
C15—C14—H14	120.1	H26A—C26—H26C	109.5
C16—C15—C14	122.5 (5)	H26B—C26—H26C	109.5
C16—C15—H15	118.8	C21—O1—C20	116.8 (2)
C14—C15—H15	118.8	C21—O3—C22	117.3 (3)
C15—C16—C17	119.7 (6)	C24—O4—C9	116.35 (16)
C15—C16—H16	120.2	C24—O6—C25	116.6 (2)
C6—C1—C2—C3	0.2 (3)	C11—C12—C13—C14	−179.0 (2)
C10—C1—C2—C3	−178.6 (2)	C12—C13—C14—C15	−0.1 (5)
C1—C2—C3—C4	−0.5 (4)	C13—C14—C15—C16	−0.9 (8)
C2—C3—C4—C5	0.4 (4)	C14—C15—C16—C17	1.1 (9)
C3—C4—C5—C6	0.0 (4)	C13—C12—C17—C18	178.7 (3)
C2—C1—C6—C7	−179.42 (19)	C11—C12—C17—C18	−1.3 (4)
C10—C1—C6—C7	−0.6 (3)	C13—C12—C17—C16	−0.8 (4)
C2—C1—C6—C5	0.2 (3)	C11—C12—C17—C16	179.2 (3)
C10—C1—C6—C5	179.01 (19)	C15—C16—C17—C18	−179.7 (5)
C4—C5—C6—C1	−0.3 (3)	C15—C16—C17—C12	−0.2 (7)
C4—C5—C6—C7	179.3 (2)	C12—C17—C18—C19	1.6 (5)
C1—C6—C7—C8	1.0 (3)	C16—C17—C18—C19	−178.9 (3)
C5—C6—C7—C8	−178.6 (2)	C17—C18—C19—C20	−0.3 (5)
C6—C7—C8—C9	−0.5 (4)	C12—C11—C20—O1	176.90 (17)
C7—C8—C9—C10	−0.4 (3)	C10—C11—C20—O1	−0.8 (3)
C7—C8—C9—O4	−174.9 (2)	C12—C11—C20—C19	1.6 (3)
C8—C9—C10—C1	0.7 (3)	C10—C11—C20—C19	−176.1 (2)
O4—C9—C10—C1	175.26 (17)	C18—C19—C20—C11	−1.3 (4)
C8—C9—C10—C11	−175.4 (2)	C18—C19—C20—O1	−176.5 (2)
O4—C9—C10—C11	−0.9 (3)	O2—C21—O1—C20	0.2 (4)
C6—C1—C10—C9	−0.2 (3)	O3—C21—O1—C20	−178.5 (2)
C2—C1—C10—C9	178.54 (18)	C11—C20—O1—C21	121.8 (2)
C6—C1—C10—C11	175.95 (19)	C19—C20—O1—C21	−62.7 (3)
C2—C1—C10—C11	−5.3 (3)	O2—C21—O3—C22	−1.2 (4)
C9—C10—C11—C20	−95.4 (2)	O1—C21—O3—C22	177.5 (3)
C1—C10—C11—C20	88.6 (2)	C23—C22—O3—C21	−128.4 (6)
C9—C10—C11—C12	86.9 (2)	O5—C24—O4—C9	2.6 (3)
C1—C10—C11—C12	−89.1 (2)	O6—C24—O4—C9	−177.10 (18)
C20—C11—C12—C13	179.7 (2)	C10—C9—O4—C24	100.8 (2)
C10—C11—C12—C13	−2.5 (3)	C8—C9—O4—C24	−84.4 (2)
C20—C11—C12—C17	−0.2 (3)	O5—C24—O6—C25	−2.2 (4)
C10—C11—C12—C17	177.52 (19)	O4—C24—O6—C25	177.5 (2)
C17—C12—C13—C14	1.0 (4)	C26—C25—O6—C24	79.9 (3)

(393K) 1,1'-binaphthalene-2,2'-diyl diethyl bis(carbonate)

Crystal data

C26H22O6	Z = 2
Mr = 430.44	F(000) = 452
Triclinic, P1	Dx = 1.265 Mg m^−3
Hall symbol: -P 1	Melting point: 417.67 K
a = 9.8546 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0864 (19) Å	Cell parameters from 450 reflections
c = 12.539 (2) Å	θ = 0.9–28.0°
α = 89.469 (4)°	µ = 0.09 mm^−1
β = 85.207 (4)°	T = 393 K
γ = 65.578 (3)°	Block, colourless
V = 1130.4 (3) Å^3	0.50 × 0.31 × 0.25 mm

Data collection

Bruker SMART CCD area detector diffractometer	4606 independent reflections
Radiation source: fine-focus sealed tube	2113 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ϕ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.909, Tmax = 0.978	k = −12→12
12123 measured reflections	l = −15→15

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.220	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.1049P)^2 + 0.0489P] where P = (Fo^2 + 2Fc^2)/3
4606 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

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

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

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

	x	y	z	Uiso*/Ueq
C9	0.4676 (3)	0.4121 (3)	0.2136 (2)	0.0823 (7)
C8	0.5634 (4)	0.4807 (3)	0.2248 (3)	0.1059 (9)
H8	0.5755	0.5415	0.1722	0.127*
C7	0.6380 (3)	0.4568 (4)	0.3137 (3)	0.1100 (11)
H7	0.7028	0.5012	0.3215	0.132*
C6	0.6202 (3)	0.3660 (3)	0.3953 (3)	0.0907 (8)
C5	0.6952 (3)	0.3431 (4)	0.4899 (4)	0.1178 (12)
H5	0.7590	0.3880	0.4995	0.141*
C4	0.6745 (4)	0.2563 (5)	0.5660 (3)	0.1305 (14)
H4	0.7246	0.2414	0.6277	0.157*
C3	0.5801 (4)	0.1899 (4)	0.5532 (2)	0.1200 (11)
H3	0.5658	0.1317	0.6070	0.144*
C2	0.5071 (3)	0.2078 (3)	0.4632 (2)	0.0939 (8)
H2	0.4451	0.1603	0.4555	0.113*
C1	0.5246 (2)	0.2975 (3)	0.38136 (19)	0.0741 (7)
C10	0.4465 (3)	0.3221 (2)	0.28768 (18)	0.0711 (6)
C11	0.3517 (3)	0.2437 (3)	0.26877 (19)	0.0819 (7)
C12	0.4182 (5)	0.1051 (3)	0.2127 (2)	0.1033 (10)
C13	0.5704 (6)	0.0449 (4)	0.1702 (3)	0.1303 (13)
H13	0.6302	0.0943	0.1799	0.156*
C14	0.6292 (8)	−0.0873 (5)	0.1146 (3)	0.185 (2)
H14	0.7284	−0.1266	0.0860	0.222*
C15	0.5395 (13)	−0.1612 (9)	0.1016 (7)	0.236 (6)
H15	0.5804	−0.2499	0.0638	0.284*
C16	0.3984 (12)	−0.1098 (7)	0.1411 (6)	0.211 (4)
H16	0.3421	−0.1628	0.1314	0.253*
C17	0.3314 (8)	0.0272 (5)	0.1990 (3)	0.1428 (17)
C18	0.1821 (9)	0.0866 (7)	0.2427 (5)	0.173 (3)
H18	0.1244	0.0346	0.2346	0.208*
C19	0.1185 (5)	0.2178 (6)	0.2967 (3)	0.1450 (16)
H19	0.0195	0.2547	0.3257	0.174*
C20	0.2061 (4)	0.2951 (4)	0.3071 (3)	0.0981 (9)
C21	0.0277 (4)	0.5372 (5)	0.3321 (3)	0.1146 (11)
C22	−0.1321 (5)	0.7855 (7)	0.3744 (5)	0.193 (2)
H22A	−0.1686	0.7727	0.3075	0.231*
H22B	−0.2126	0.8056	0.4304	0.231*
C23	−0.0969 (7)	0.8987 (7)	0.3675 (8)	0.271 (4)
H23A	−0.0584	0.9106	0.4328	0.406*
H23B	−0.1845	0.9850	0.3558	0.406*
H23C	−0.0222	0.8826	0.3088	0.406*
C24	0.2760 (4)	0.5497 (4)	0.1086 (2)	0.0918 (8)
C25	0.0881 (6)	0.6574 (6)	−0.0097 (4)	0.1675 (17)
H25A	0.0460	0.6229	−0.0647	0.201*
H25B	0.0179	0.6836	0.0537	0.201*
C26	0.1087 (7)	0.7799 (7)	−0.0452 (5)	0.221 (3)
H26A	0.1338	0.8239	0.0132	0.332*
H26B	0.0182	0.8486	−0.0717	0.332*
H26C	0.1884	0.7513	−0.1014	0.332*
O1	0.1472 (2)	0.4271 (3)	0.36652 (15)	0.1072 (7)
O2	−0.0321 (3)	0.5314 (3)	0.2544 (2)	0.1511 (10)
O3	−0.0057 (3)	0.6493 (4)	0.3976 (2)	0.1366 (9)
O4	0.3986 (3)	0.4290 (2)	0.11726 (13)	0.1001 (6)
O5	0.2275 (3)	0.5428 (3)	0.01496 (16)	0.1252 (8)
O6	0.2217 (2)	0.6446 (3)	0.17393 (18)	0.1189 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C9	0.0893 (18)	0.0724 (15)	0.0784 (17)	−0.0280 (14)	0.0012 (14)	−0.0010 (13)
C8	0.103 (2)	0.088 (2)	0.126 (3)	−0.0442 (19)	0.018 (2)	−0.0016 (18)
C7	0.0753 (19)	0.099 (2)	0.161 (3)	−0.0432 (17)	0.003 (2)	−0.023 (2)
C6	0.0632 (16)	0.0860 (18)	0.113 (2)	−0.0214 (15)	−0.0047 (15)	−0.0203 (17)
C5	0.0738 (19)	0.120 (3)	0.146 (3)	−0.0222 (19)	−0.030 (2)	−0.038 (2)
C4	0.106 (3)	0.147 (3)	0.113 (3)	−0.019 (3)	−0.050 (2)	−0.021 (3)
C3	0.119 (3)	0.130 (3)	0.092 (2)	−0.027 (2)	−0.0423 (19)	0.0096 (18)
C2	0.0957 (19)	0.104 (2)	0.0793 (17)	−0.0360 (16)	−0.0231 (15)	0.0092 (15)
C1	0.0612 (14)	0.0752 (15)	0.0779 (16)	−0.0196 (13)	−0.0097 (12)	−0.0067 (12)
C10	0.0739 (15)	0.0684 (14)	0.0703 (14)	−0.0289 (12)	−0.0050 (12)	−0.0003 (12)
C11	0.107 (2)	0.0892 (19)	0.0649 (14)	−0.0526 (17)	−0.0276 (14)	0.0185 (13)
C12	0.174 (3)	0.086 (2)	0.0731 (17)	−0.070 (2)	−0.050 (2)	0.0239 (16)
C13	0.195 (4)	0.081 (2)	0.096 (2)	−0.038 (2)	−0.011 (2)	0.0025 (18)
C14	0.303 (7)	0.082 (3)	0.121 (3)	−0.033 (3)	−0.010 (3)	−0.009 (2)
C15	0.474 (16)	0.104 (5)	0.133 (5)	−0.110 (8)	−0.097 (7)	0.016 (4)
C16	0.437 (13)	0.115 (5)	0.147 (6)	−0.158 (7)	−0.151 (7)	0.051 (4)
C17	0.250 (5)	0.113 (3)	0.115 (3)	−0.111 (4)	−0.101 (3)	0.051 (2)
C18	0.255 (7)	0.182 (5)	0.181 (5)	−0.170 (6)	−0.137 (5)	0.095 (4)
C19	0.154 (3)	0.193 (4)	0.147 (3)	−0.122 (4)	−0.069 (3)	0.072 (3)
C20	0.111 (2)	0.124 (3)	0.0896 (19)	−0.073 (2)	−0.0412 (18)	0.0306 (19)
C21	0.077 (2)	0.169 (4)	0.113 (3)	−0.065 (2)	−0.023 (2)	0.040 (3)
C22	0.102 (3)	0.196 (5)	0.245 (6)	−0.021 (4)	−0.046 (3)	0.050 (5)
C23	0.158 (5)	0.163 (5)	0.442 (13)	−0.009 (5)	−0.069 (6)	0.001 (7)
C24	0.102 (2)	0.097 (2)	0.0776 (19)	−0.0431 (19)	−0.0020 (17)	0.0007 (17)
C25	0.200 (5)	0.152 (4)	0.139 (3)	−0.053 (4)	−0.056 (3)	0.016 (3)
C26	0.217 (6)	0.187 (5)	0.203 (5)	−0.014 (5)	−0.084 (4)	0.001 (5)
O1	0.0784 (13)	0.1540 (19)	0.0913 (13)	−0.0479 (13)	−0.0214 (10)	0.0186 (13)
O2	0.1265 (19)	0.190 (3)	0.159 (2)	−0.0774 (18)	−0.0736 (17)	0.0463 (19)
O3	0.0937 (17)	0.162 (2)	0.1313 (19)	−0.0298 (17)	−0.0134 (14)	0.0085 (18)
O4	0.1336 (17)	0.0802 (12)	0.0721 (11)	−0.0306 (12)	−0.0065 (11)	0.0088 (9)
O5	0.153 (2)	0.1263 (18)	0.0842 (14)	−0.0423 (16)	−0.0267 (13)	0.0101 (12)
O6	0.1020 (15)	0.1224 (16)	0.1077 (15)	−0.0204 (13)	−0.0145 (12)	−0.0206 (14)

Geometric parameters (Å, º)

C9—C10	1.355 (3)	C16—C17	1.434 (8)
C9—C8	1.398 (4)	C16—H16	0.9300
C9—O4	1.411 (3)	C17—C18	1.402 (7)
C8—C7	1.352 (4)	C18—C19	1.365 (7)
C8—H8	0.9300	C18—H18	0.9300
C7—C6	1.415 (4)	C19—C20	1.396 (5)
C7—H7	0.9300	C19—H19	0.9300
C6—C1	1.401 (4)	C20—O1	1.404 (4)
C6—C5	1.416 (4)	C21—O2	1.194 (4)
C5—C4	1.349 (5)	C21—O3	1.313 (4)
C5—H5	0.9300	C21—O1	1.342 (4)
C4—C3	1.372 (5)	C22—C23	1.324 (7)
C4—H4	0.9300	C22—O3	1.470 (5)
C3—C2	1.360 (4)	C22—H22A	0.9700
C3—H3	0.9300	C22—H22B	0.9700
C2—C1	1.408 (3)	C23—H23A	0.9600
C2—H2	0.9300	C23—H23B	0.9600
C1—C10	1.422 (3)	C23—H23C	0.9600
C10—C11	1.484 (3)	C24—O6	1.179 (3)
C11—C20	1.354 (4)	C24—O5	1.317 (3)
C11—C12	1.436 (4)	C24—O4	1.326 (3)
C12—C17	1.401 (5)	C25—C26	1.396 (7)
C12—C13	1.422 (5)	C25—O5	1.439 (5)
C13—C14	1.382 (5)	C25—H25A	0.9700
C13—H13	0.9300	C25—H25B	0.9700
C14—C15	1.391 (11)	C26—H26A	0.9600
C14—H14	0.9300	C26—H26B	0.9600
C15—C16	1.320 (12)	C26—H26C	0.9600
C15—H15	0.9300
C10—C9—C8	123.0 (3)	C17—C16—H16	119.8
C10—C9—O4	118.6 (2)	C12—C17—C18	118.5 (5)
C8—C9—O4	118.2 (3)	C12—C17—C16	118.8 (6)
C7—C8—C9	118.6 (3)	C18—C17—C16	122.7 (6)
C7—C8—H8	120.7	C19—C18—C17	122.4 (5)
C9—C8—H8	120.7	C19—C18—H18	118.8
C8—C7—C6	121.7 (3)	C17—C18—H18	118.8
C8—C7—H7	119.1	C18—C19—C20	118.1 (5)
C6—C7—H7	119.1	C18—C19—H19	120.9
C1—C6—C7	118.4 (3)	C20—C19—H19	120.9
C1—C6—C5	119.5 (3)	C11—C20—C19	122.9 (4)
C7—C6—C5	122.1 (3)	C11—C20—O1	117.0 (3)
C4—C5—C6	120.3 (3)	C19—C20—O1	119.8 (4)
C4—C5—H5	119.8	O2—C21—O3	127.9 (4)
C6—C5—H5	119.8	O2—C21—O1	124.8 (5)
C5—C4—C3	120.5 (3)	O3—C21—O1	107.2 (3)
C5—C4—H4	119.8	C23—C22—O3	113.2 (5)
C3—C4—H4	119.8	C23—C22—H22A	108.9
C2—C3—C4	121.1 (4)	O3—C22—H22A	108.9
C2—C3—H3	119.5	C23—C22—H22B	108.9
C4—C3—H3	119.5	O3—C22—H22B	108.9
C3—C2—C1	120.6 (3)	H22A—C22—H22B	107.8
C3—C2—H2	119.7	C22—C23—H23A	109.5
C1—C2—H2	119.7	C22—C23—H23B	109.5
C6—C1—C2	118.0 (2)	H23A—C23—H23B	109.5
C6—C1—C10	119.9 (2)	C22—C23—H23C	109.5
C2—C1—C10	122.1 (2)	H23A—C23—H23C	109.5
C9—C10—C1	118.3 (2)	H23B—C23—H23C	109.5
C9—C10—C11	121.0 (2)	O6—C24—O5	127.1 (3)
C1—C10—C11	120.5 (2)	O6—C24—O4	125.4 (3)
C20—C11—C12	118.6 (3)	O5—C24—O4	107.4 (3)
C20—C11—C10	122.2 (3)	C26—C25—O5	111.0 (5)
C12—C11—C10	119.1 (3)	C26—C25—H25A	109.4
C17—C12—C13	119.0 (4)	O5—C25—H25A	109.4
C17—C12—C11	119.5 (4)	C26—C25—H25B	109.4
C13—C12—C11	121.5 (3)	O5—C25—H25B	109.4
C14—C13—C12	119.7 (5)	H25A—C25—H25B	108.0
C14—C13—H13	120.1	C25—C26—H26A	109.5
C12—C13—H13	120.1	C25—C26—H26B	109.5
C13—C14—C15	119.8 (7)	H26A—C26—H26B	109.5
C13—C14—H14	120.1	C25—C26—H26C	109.5
C15—C14—H14	120.1	H26A—C26—H26C	109.5
C16—C15—C14	122.2 (9)	H26B—C26—H26C	109.5
C16—C15—H15	118.9	C21—O1—C20	117.7 (3)
C14—C15—H15	118.9	C21—O3—C22	117.3 (4)
C15—C16—C17	120.4 (9)	C24—O4—C9	116.9 (2)
C15—C16—H16	119.8	C24—O5—C25	117.8 (3)
C10—C9—C8—C7	−0.3 (4)	C11—C12—C13—C14	−178.5 (3)
O4—C9—C8—C7	−175.4 (3)	C12—C13—C14—C15	−0.7 (7)
C9—C8—C7—C6	−0.7 (4)	C13—C14—C15—C16	−0.3 (12)
C8—C7—C6—C1	1.3 (4)	C14—C15—C16—C17	0.6 (14)
C8—C7—C6—C5	−178.5 (3)	C13—C12—C17—C18	179.0 (3)
C1—C6—C5—C4	−0.2 (4)	C11—C12—C17—C18	−1.2 (5)
C7—C6—C5—C4	179.6 (3)	C13—C12—C17—C16	−0.9 (5)
C6—C5—C4—C3	−0.4 (5)	C11—C12—C17—C16	178.9 (3)
C5—C4—C3—C2	1.1 (5)	C15—C16—C17—C12	0.0 (10)
C4—C3—C2—C1	−1.2 (5)	C15—C16—C17—C18	−179.9 (7)
C7—C6—C1—C2	−179.7 (2)	C12—C17—C18—C19	0.8 (6)
C5—C6—C1—C2	0.0 (3)	C16—C17—C18—C19	−179.3 (4)
C7—C6—C1—C10	−1.0 (3)	C17—C18—C19—C20	0.7 (6)
C5—C6—C1—C10	178.7 (2)	C12—C11—C20—C19	1.6 (4)
C3—C2—C1—C6	0.7 (4)	C10—C11—C20—C19	−175.2 (3)
C3—C2—C1—C10	−178.0 (2)	C12—C11—C20—O1	176.6 (2)
C8—C9—C10—C1	0.5 (4)	C10—C11—C20—O1	−0.2 (4)
O4—C9—C10—C1	175.7 (2)	C18—C19—C20—C11	−2.0 (5)
C8—C9—C10—C11	−175.7 (2)	C18—C19—C20—O1	−176.9 (3)
O4—C9—C10—C11	−0.6 (3)	O2—C21—O1—C20	−0.2 (4)
C6—C1—C10—C9	0.2 (3)	O3—C21—O1—C20	−178.6 (2)
C2—C1—C10—C9	178.8 (2)	C11—C20—O1—C21	122.5 (3)
C6—C1—C10—C11	176.4 (2)	C19—C20—O1—C21	−62.3 (3)
C2—C1—C10—C11	−4.9 (3)	O2—C21—O3—C22	0.3 (6)
C9—C10—C11—C20	−96.2 (3)	O1—C21—O3—C22	178.6 (3)
C1—C10—C11—C20	87.6 (3)	C23—C22—O3—C21	−125.9 (7)
C9—C10—C11—C12	87.0 (3)	O6—C24—O4—C9	1.2 (4)
C1—C10—C11—C12	−89.2 (3)	O5—C24—O4—C9	−178.5 (2)
C20—C11—C12—C17	0.1 (4)	C10—C9—O4—C24	102.2 (3)
C10—C11—C12—C17	177.0 (2)	C8—C9—O4—C24	−82.4 (3)
C20—C11—C12—C13	179.9 (3)	O6—C24—O5—C25	−4.3 (5)
C10—C11—C12—C13	−3.2 (4)	O4—C24—O5—C25	175.3 (3)
C17—C12—C13—C14	1.3 (5)	C26—C25—O5—C24	81.1 (5)

(150K) 1,1'-binaphthalene-2,2'-diyl diethyl bis(carbonate)

Crystal data

C26H22O6	Z = 4
Mr = 430.44	F(000) = 904
Triclinic, P1	Dx = 1.336 Mg m^−3
Hall symbol: -P 1	Melting point: 417.67 K
a = 10.8028 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.798 (3) Å	Cell parameters from 615 reflections
c = 15.926 (3) Å	θ = 0.9–28.0°
α = 63.692 (2)°	µ = 0.10 mm^−1
β = 72.394 (3)°	T = 150 K
γ = 73.200 (3)°	Block, colourless
V = 2139.2 (7) Å^3	0.50 × 0.31 × 0.25 mm

Data collection

Bruker SMART CCD area detector diffractometer	8704 independent reflections
Radiation source: fine-focus sealed tube	6807 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ϕ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.906, Tmax = 0.977	k = −18→18
22856 measured reflections	l = −19→19

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0697P)^2 + 0.7813P] where P = (Fo^2 + 2Fc^2)/3
8704 reflections	(Δ/σ)max < 0.001
581 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

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

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

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

	x	y	z	Uiso*/Ueq
C9	0.88531 (17)	0.66802 (13)	0.53583 (12)	0.0301 (4)
C8	0.86489 (19)	0.58282 (14)	0.62148 (14)	0.0375 (4)
H8	0.9185	0.5176	0.6280	0.045*
C7	0.76734 (19)	0.59438 (15)	0.69546 (14)	0.0409 (5)
H7	0.7536	0.5367	0.7539	0.049*
C6	0.68609 (18)	0.69068 (15)	0.68679 (13)	0.0359 (4)
C5	0.5870 (2)	0.70589 (19)	0.76367 (14)	0.0474 (5)
H5	0.5724	0.6494	0.8230	0.057*
C4	0.5123 (2)	0.7999 (2)	0.75396 (16)	0.0527 (6)
H4	0.4477	0.8090	0.8067	0.063*
C3	0.5304 (2)	0.88385 (18)	0.66612 (16)	0.0487 (5)
H3	0.4766	0.9490	0.6595	0.058*
C2	0.62456 (18)	0.87264 (15)	0.59011 (14)	0.0374 (4)
H2	0.6354	0.9301	0.5311	0.045*
C1	0.70627 (16)	0.77624 (14)	0.59825 (12)	0.0303 (4)
C10	0.80967 (16)	0.76329 (13)	0.52119 (12)	0.0270 (4)
C11	0.83061 (16)	0.85082 (13)	0.42699 (12)	0.0285 (4)
C12	0.76089 (17)	0.87052 (15)	0.35535 (13)	0.0351 (4)
C13	0.67404 (19)	0.80690 (18)	0.37007 (17)	0.0473 (5)
H13	0.6569	0.7516	0.4299	0.057*
C14	0.6143 (2)	0.8254 (2)	0.2973 (2)	0.0631 (7)
H14	0.5567	0.7821	0.3073	0.076*
C15	0.6378 (2)	0.9072 (2)	0.20887 (19)	0.0688 (9)
H15	0.5982	0.9177	0.1587	0.083*
C16	0.7167 (2)	0.9716 (2)	0.19449 (16)	0.0607 (7)
H16	0.7287	1.0283	0.1350	0.073*
C17	0.78115 (19)	0.95580 (16)	0.26613 (13)	0.0429 (5)
C18	0.8647 (2)	1.02079 (16)	0.25272 (14)	0.0478 (5)
H18	0.8751	1.0794	0.1946	0.057*
C19	0.9305 (2)	1.00156 (15)	0.32084 (13)	0.0417 (5)
H19	0.9867	1.0459	0.3107	0.050*
C20	0.91428 (17)	0.91493 (13)	0.40667 (12)	0.0308 (4)
C21	1.11330 (18)	0.87624 (13)	0.45672 (13)	0.0352 (4)
C22	1.2960 (2)	0.8445 (3)	0.5246 (2)	0.0839 (10)
H22A	1.3412	0.8404	0.4619	0.101*
H22B	1.3231	0.9014	0.5275	0.101*
C23	1.3368 (3)	0.7566 (3)	0.5942 (3)	0.1322 (19)
H23A	1.2810	0.7543	0.6562	0.198*
H23B	1.4287	0.7528	0.5946	0.198*
H23C	1.3305	0.6984	0.5828	0.198*
C24	1.10839 (17)	0.64031 (13)	0.46319 (12)	0.0296 (4)
C25	1.3244 (2)	0.61181 (19)	0.37615 (15)	0.0492 (5)
H25A	1.3447	0.6573	0.3988	0.059*
H25B	1.3692	0.6291	0.3082	0.059*
C26	1.3759 (2)	0.5030 (2)	0.43362 (16)	0.0549 (6)
H26A	1.3347	0.4866	0.5013	0.082*
H26B	1.4719	0.4930	0.4255	0.082*
H26C	1.3550	0.4577	0.4118	0.082*
C9'	0.65209 (16)	0.84072 (12)	−0.05936 (12)	0.0261 (3)
C8'	0.66681 (18)	0.91318 (13)	−0.15391 (13)	0.0326 (4)
H8'	0.6143	0.9799	−0.1693	0.039*
C7'	0.75771 (18)	0.88624 (14)	−0.22322 (12)	0.0334 (4)
H7'	0.7693	0.9352	−0.2873	0.040*
C6'	0.83525 (16)	0.78688 (13)	−0.20170 (11)	0.0272 (4)
C5'	0.93010 (17)	0.75710 (15)	−0.27287 (12)	0.0350 (4)
H5'	0.9439	0.8055	−0.3371	0.042*
C4'	1.00187 (17)	0.66022 (16)	−0.25068 (13)	0.0377 (4)
H4'	1.0651	0.6417	−0.2994	0.045*
C3'	0.98268 (17)	0.58778 (15)	−0.15622 (13)	0.0358 (4)
H3'	1.0319	0.5200	−0.1415	0.043*
C2'	0.89383 (16)	0.61386 (13)	−0.08533 (12)	0.0285 (4)
H2'	0.8830	0.5643	−0.0215	0.034*
C1'	0.81749 (15)	0.71388 (12)	−0.10563 (11)	0.0235 (3)
C10'	0.72427 (15)	0.74340 (12)	−0.03325 (11)	0.0227 (3)
C11'	0.71286 (15)	0.67215 (12)	0.06926 (11)	0.0239 (3)
C12'	0.79007 (16)	0.67694 (12)	0.12552 (11)	0.0265 (4)
C13'	0.87661 (17)	0.74736 (14)	0.08752 (13)	0.0326 (4)
H13'	0.8834	0.7944	0.0227	0.039*
C14'	0.95090 (19)	0.74904 (16)	0.14263 (15)	0.0415 (5)
H14'	1.0089	0.7969	0.1156	0.050*
C15'	0.9424 (2)	0.68083 (18)	0.23856 (15)	0.0463 (5)
H15'	0.9940	0.6828	0.2764	0.056*
C16'	0.85976 (19)	0.61167 (16)	0.27742 (13)	0.0412 (5)
H16'	0.8545	0.5657	0.3425	0.049*
C17'	0.78184 (17)	0.60691 (14)	0.22295 (12)	0.0313 (4)
C18'	0.69883 (18)	0.53345 (15)	0.26066 (12)	0.0366 (4)
H18'	0.6937	0.4860	0.3253	0.044*
C19'	0.62607 (18)	0.52923 (14)	0.20625 (13)	0.0349 (4)
H19'	0.5709	0.4795	0.2325	0.042*
C20'	0.63401 (16)	0.59991 (13)	0.11036 (12)	0.0273 (4)
C21'	0.43476 (17)	0.60739 (13)	0.07454 (12)	0.0303 (4)
C22'	0.2503 (2)	0.6301 (2)	0.01457 (18)	0.0619 (7)
H22C	0.2153	0.5668	0.0594	0.074*
H22D	0.2098	0.6833	0.0414	0.074*
C23'	0.2168 (2)	0.6646 (2)	−0.07797 (19)	0.0620 (6)
H23D	0.2478	0.7292	−0.1211	0.093*
H23E	0.1208	0.6753	−0.0701	0.093*
H23F	0.2593	0.6126	−0.1051	0.093*
C24'	0.44117 (16)	0.85632 (12)	0.03596 (12)	0.0271 (4)
C25'	0.2437 (2)	0.86349 (16)	0.14989 (14)	0.0436 (5)
H25C	0.2178	0.8549	0.2178	0.052*
H25D	0.2331	0.8010	0.1465	0.052*
C26'	0.1550 (2)	0.95425 (17)	0.09355 (16)	0.0487 (5)
H26D	0.1690	1.0167	0.0937	0.073*
H26E	0.0628	0.9464	0.1225	0.073*
H26F	0.1750	0.9592	0.0276	0.073*
O1'	0.56796 (11)	0.59333 (9)	0.05038 (8)	0.0310 (3)
O2'	0.36942 (12)	0.61512 (11)	0.14712 (9)	0.0402 (3)
O3'	0.39300 (12)	0.61031 (11)	0.00350 (10)	0.0394 (3)
O4'	0.56635 (11)	0.87177 (9)	0.01344 (9)	0.0314 (3)
O5'	0.39527 (12)	0.83001 (10)	−0.00720 (9)	0.0341 (3)
O3	1.15425 (13)	0.86851 (12)	0.53001 (10)	0.0479 (4)
O1	0.97992 (12)	0.89703 (9)	0.47804 (8)	0.0329 (3)
O2	1.17874 (14)	0.86644 (11)	0.38475 (10)	0.0491 (4)
O6'	0.38202 (12)	0.87517 (10)	0.11379 (9)	0.0371 (3)
O4	0.98174 (12)	0.65430 (10)	0.45787 (9)	0.0350 (3)
O6	1.18207 (13)	0.62973 (10)	0.38380 (9)	0.0398 (3)
O5	1.14496 (12)	0.63774 (11)	0.52801 (9)	0.0373 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C9	0.0281 (9)	0.0341 (9)	0.0336 (9)	−0.0039 (7)	−0.0095 (7)	−0.0169 (8)
C8	0.0382 (10)	0.0291 (9)	0.0468 (11)	−0.0063 (8)	−0.0172 (9)	−0.0104 (8)
C7	0.0416 (11)	0.0400 (11)	0.0378 (10)	−0.0204 (9)	−0.0118 (9)	−0.0019 (9)
C6	0.0309 (9)	0.0461 (11)	0.0321 (9)	−0.0189 (8)	−0.0036 (7)	−0.0109 (8)
C5	0.0386 (11)	0.0695 (15)	0.0338 (10)	−0.0292 (11)	0.0042 (8)	−0.0154 (10)
C4	0.0364 (11)	0.0826 (17)	0.0441 (12)	−0.0239 (11)	0.0147 (9)	−0.0358 (12)
C3	0.0331 (11)	0.0619 (14)	0.0531 (13)	−0.0070 (10)	0.0044 (9)	−0.0337 (11)
C2	0.0286 (9)	0.0444 (11)	0.0386 (10)	−0.0059 (8)	−0.0005 (8)	−0.0200 (9)
C1	0.0236 (8)	0.0396 (10)	0.0307 (9)	−0.0102 (7)	−0.0030 (7)	−0.0150 (8)
C10	0.0245 (8)	0.0313 (9)	0.0283 (8)	−0.0065 (7)	−0.0063 (7)	−0.0127 (7)
C11	0.0253 (8)	0.0321 (9)	0.0258 (8)	0.0031 (7)	−0.0040 (7)	−0.0150 (7)
C12	0.0288 (9)	0.0438 (10)	0.0336 (10)	0.0109 (8)	−0.0094 (7)	−0.0246 (8)
C13	0.0339 (11)	0.0639 (14)	0.0575 (13)	0.0066 (10)	−0.0162 (9)	−0.0403 (12)
C14	0.0385 (12)	0.0931 (19)	0.0873 (19)	0.0169 (12)	−0.0293 (12)	−0.0680 (17)
C15	0.0503 (14)	0.109 (2)	0.0624 (16)	0.0374 (15)	−0.0358 (13)	−0.0629 (17)
C16	0.0502 (13)	0.0862 (18)	0.0399 (12)	0.0324 (13)	−0.0222 (10)	−0.0383 (12)
C17	0.0372 (10)	0.0540 (12)	0.0293 (10)	0.0202 (9)	−0.0104 (8)	−0.0242 (9)
C18	0.0492 (12)	0.0449 (12)	0.0258 (10)	0.0069 (10)	0.0008 (9)	−0.0080 (9)
C19	0.0418 (11)	0.0375 (10)	0.0321 (10)	−0.0057 (8)	0.0032 (8)	−0.0095 (8)
C20	0.0301 (9)	0.0337 (9)	0.0239 (8)	−0.0040 (7)	−0.0001 (7)	−0.0118 (7)
C21	0.0314 (9)	0.0280 (9)	0.0331 (10)	−0.0081 (7)	0.0005 (8)	−0.0034 (8)
C22	0.0305 (12)	0.117 (3)	0.0653 (17)	−0.0192 (14)	−0.0124 (12)	0.0030 (17)
C23	0.0530 (18)	0.112 (3)	0.155 (4)	−0.0312 (18)	−0.051 (2)	0.043 (3)
C24	0.0346 (9)	0.0288 (9)	0.0274 (9)	−0.0051 (7)	−0.0067 (7)	−0.0129 (7)
C25	0.0386 (11)	0.0784 (16)	0.0359 (11)	−0.0163 (11)	0.0065 (9)	−0.0324 (11)
C26	0.0330 (11)	0.0853 (18)	0.0487 (13)	−0.0033 (11)	−0.0079 (9)	−0.0330 (13)
C9'	0.0245 (8)	0.0281 (8)	0.0305 (9)	−0.0030 (7)	−0.0077 (7)	−0.0152 (7)
C8'	0.0352 (10)	0.0246 (8)	0.0377 (10)	−0.0028 (7)	−0.0162 (8)	−0.0079 (7)
C7'	0.0373 (10)	0.0339 (9)	0.0255 (9)	−0.0127 (8)	−0.0103 (7)	−0.0021 (7)
C6'	0.0249 (8)	0.0351 (9)	0.0239 (8)	−0.0123 (7)	−0.0049 (6)	−0.0095 (7)
C5'	0.0310 (9)	0.0543 (12)	0.0214 (8)	−0.0181 (8)	0.0009 (7)	−0.0138 (8)
C4'	0.0262 (9)	0.0606 (13)	0.0323 (10)	−0.0072 (8)	0.0031 (7)	−0.0294 (9)
C3'	0.0283 (9)	0.0444 (11)	0.0370 (10)	0.0012 (8)	−0.0046 (8)	−0.0238 (9)
C2'	0.0255 (8)	0.0338 (9)	0.0256 (8)	−0.0024 (7)	−0.0044 (7)	−0.0133 (7)
C1'	0.0187 (7)	0.0310 (8)	0.0231 (8)	−0.0069 (6)	−0.0033 (6)	−0.0119 (7)
C10'	0.0209 (8)	0.0264 (8)	0.0222 (8)	−0.0066 (6)	−0.0046 (6)	−0.0091 (6)
C11'	0.0224 (8)	0.0254 (8)	0.0218 (8)	0.0007 (6)	−0.0013 (6)	−0.0125 (7)
C12'	0.0242 (8)	0.0289 (8)	0.0255 (8)	0.0037 (7)	−0.0045 (6)	−0.0154 (7)
C13'	0.0327 (9)	0.0345 (9)	0.0336 (9)	−0.0002 (7)	−0.0107 (7)	−0.0171 (8)
C14'	0.0354 (10)	0.0494 (12)	0.0503 (12)	−0.0034 (9)	−0.0156 (9)	−0.0269 (10)
C15'	0.0376 (11)	0.0680 (14)	0.0448 (12)	0.0062 (10)	−0.0200 (9)	−0.0342 (11)
C16'	0.0349 (10)	0.0572 (13)	0.0270 (9)	0.0104 (9)	−0.0115 (8)	−0.0205 (9)
C17'	0.0271 (9)	0.0375 (10)	0.0235 (8)	0.0062 (7)	−0.0036 (7)	−0.0150 (7)
C18'	0.0326 (10)	0.0404 (10)	0.0222 (8)	0.0019 (8)	−0.0002 (7)	−0.0080 (8)
C19'	0.0319 (9)	0.0327 (9)	0.0293 (9)	−0.0069 (7)	0.0050 (7)	−0.0091 (8)
C20'	0.0247 (8)	0.0308 (9)	0.0260 (8)	−0.0022 (7)	−0.0009 (7)	−0.0151 (7)
C21'	0.0295 (9)	0.0278 (9)	0.0333 (9)	−0.0119 (7)	0.0013 (7)	−0.0125 (7)
C22'	0.0299 (11)	0.108 (2)	0.0606 (15)	−0.0248 (12)	−0.0003 (10)	−0.0424 (15)
C23'	0.0386 (12)	0.0725 (17)	0.0722 (17)	−0.0086 (11)	−0.0145 (11)	−0.0247 (14)
C24'	0.0315 (9)	0.0219 (8)	0.0261 (8)	−0.0020 (7)	−0.0058 (7)	−0.0094 (7)
C25'	0.0461 (12)	0.0475 (12)	0.0374 (10)	−0.0174 (9)	0.0107 (9)	−0.0237 (9)
C26'	0.0357 (11)	0.0577 (13)	0.0566 (13)	−0.0104 (10)	0.0030 (9)	−0.0324 (11)
O1'	0.0274 (6)	0.0376 (7)	0.0320 (6)	−0.0099 (5)	0.0014 (5)	−0.0194 (5)
O2'	0.0322 (7)	0.0503 (8)	0.0327 (7)	−0.0119 (6)	0.0049 (6)	−0.0160 (6)
O3'	0.0296 (7)	0.0528 (8)	0.0457 (8)	−0.0129 (6)	−0.0016 (6)	−0.0283 (7)
O4'	0.0271 (6)	0.0347 (6)	0.0395 (7)	0.0027 (5)	−0.0093 (5)	−0.0242 (6)
O5'	0.0337 (7)	0.0420 (7)	0.0315 (6)	−0.0121 (6)	−0.0006 (5)	−0.0194 (6)
O3	0.0315 (7)	0.0650 (10)	0.0416 (8)	−0.0123 (7)	−0.0076 (6)	−0.0136 (7)
O1	0.0302 (6)	0.0405 (7)	0.0283 (6)	−0.0114 (5)	−0.0002 (5)	−0.0144 (5)
O2	0.0401 (8)	0.0514 (9)	0.0348 (7)	−0.0031 (6)	0.0063 (6)	−0.0105 (7)
O6'	0.0392 (7)	0.0420 (7)	0.0334 (7)	−0.0049 (6)	−0.0018 (6)	−0.0228 (6)
O4	0.0341 (7)	0.0403 (7)	0.0364 (7)	0.0046 (5)	−0.0130 (5)	−0.0231 (6)
O6	0.0401 (7)	0.0519 (8)	0.0322 (7)	−0.0014 (6)	−0.0066 (6)	−0.0252 (6)
O5	0.0344 (7)	0.0552 (8)	0.0297 (7)	−0.0160 (6)	−0.0009 (5)	−0.0217 (6)

Geometric parameters (Å, º)

C9—C10	1.367 (2)	C9'—C10'	1.368 (2)
C9—C8	1.398 (3)	C9'—C8'	1.402 (2)
C9—O4	1.409 (2)	C9'—O4'	1.4106 (19)
C8—C7	1.361 (3)	C8'—C7'	1.360 (3)
C8—H8	0.9500	C8'—H8'	0.9500
C7—C6	1.413 (3)	C7'—C6'	1.413 (2)
C7—H7	0.9500	C7'—H7'	0.9500
C6—C5	1.417 (3)	C6'—C5'	1.417 (2)
C6—C1	1.425 (3)	C6'—C1'	1.422 (2)
C5—C4	1.359 (3)	C5'—C4'	1.362 (3)
C5—H5	0.9500	C5'—H5'	0.9500
C4—C3	1.404 (3)	C4'—C3'	1.402 (3)
C4—H4	0.9500	C4'—H4'	0.9500
C3—C2	1.365 (3)	C3'—C2'	1.364 (2)
C3—H3	0.9500	C3'—H3'	0.9500
C2—C1	1.417 (3)	C2'—C1'	1.417 (2)
C2—H2	0.9500	C2'—H2'	0.9500
C1—C10	1.430 (2)	C1'—C10'	1.423 (2)
C10—C11	1.490 (2)	C10'—C11'	1.490 (2)
C11—C20	1.367 (2)	C11'—C20'	1.366 (2)
C11—C12	1.433 (2)	C11'—C12'	1.430 (2)
C12—C13	1.415 (3)	C12'—C13'	1.410 (2)
C12—C17	1.429 (3)	C12'—C17'	1.426 (2)
C13—C14	1.379 (3)	C13'—C14'	1.368 (2)
C13—H13	0.9500	C13'—H13'	0.9500
C14—C15	1.401 (4)	C14'—C15'	1.401 (3)
C14—H14	0.9500	C14'—H14'	0.9500
C15—C16	1.359 (4)	C15'—C16'	1.364 (3)
C15—H15	0.9500	C15'—H15'	0.9500
C16—C17	1.411 (3)	C16'—C17'	1.413 (3)
C16—H16	0.9500	C16'—H16'	0.9500
C17—C18	1.410 (3)	C17'—C18'	1.416 (3)
C18—C19	1.357 (3)	C18'—C19'	1.364 (3)
C18—H18	0.9500	C18'—H18'	0.9500
C19—C20	1.405 (2)	C19'—C20'	1.411 (2)
C19—H19	0.9500	C19'—H19'	0.9500
C20—O1	1.406 (2)	C20'—O1'	1.402 (2)
C21—O2	1.197 (2)	C21'—O2'	1.194 (2)
C21—O3	1.317 (2)	C21'—O3'	1.319 (2)
C21—O1	1.352 (2)	C21'—O1'	1.351 (2)
C22—C23	1.343 (4)	C22'—C23'	1.454 (3)
C22—O3	1.453 (3)	C22'—O3'	1.454 (2)
C22—H22A	0.9900	C22'—H22C	0.9900
C22—H22B	0.9900	C22'—H22D	0.9900
C23—H23A	0.9800	C23'—H23D	0.9800
C23—H23B	0.9800	C23'—H23E	0.9800
C23—H23C	0.9800	C23'—H23F	0.9800
C24—O5	1.194 (2)	C24'—O5'	1.194 (2)
C24—O6	1.323 (2)	C24'—O6'	1.322 (2)
C24—O4	1.346 (2)	C24'—O4'	1.350 (2)
C25—O6	1.459 (2)	C25'—O6'	1.461 (2)
C25—C26	1.492 (3)	C25'—C26'	1.495 (3)
C25—H25A	0.9900	C25'—H25C	0.9900
C25—H25B	0.9900	C25'—H25D	0.9900
C26—H26A	0.9800	C26'—H26D	0.9800
C26—H26B	0.9800	C26'—H26E	0.9800
C26—H26C	0.9800	C26'—H26F	0.9800
C10—C9—C8	123.22 (16)	C7'—C8'—H8'	120.6
C10—C9—O4	117.75 (15)	C9'—C8'—H8'	120.6
C8—C9—O4	118.85 (15)	C8'—C7'—C6'	121.28 (16)
C7—C8—C9	119.23 (17)	C8'—C7'—H7'	119.4
C7—C8—H8	120.4	C6'—C7'—H7'	119.4
C9—C8—H8	120.4	C7'—C6'—C5'	122.19 (16)
C8—C7—C6	121.12 (17)	C7'—C6'—C1'	119.15 (15)
C8—C7—H7	119.4	C5'—C6'—C1'	118.66 (16)
C6—C7—H7	119.4	C4'—C5'—C6'	121.11 (16)
C7—C6—C5	122.39 (18)	C4'—C5'—H5'	119.4
C7—C6—C1	118.92 (17)	C6'—C5'—H5'	119.4
C5—C6—C1	118.68 (18)	C5'—C4'—C3'	120.18 (16)
C4—C5—C6	121.1 (2)	C5'—C4'—H4'	119.9
C4—C5—H5	119.4	C3'—C4'—H4'	119.9
C6—C5—H5	119.4	C2'—C3'—C4'	120.52 (17)
C5—C4—C3	120.20 (19)	C2'—C3'—H3'	119.7
C5—C4—H4	119.9	C4'—C3'—H3'	119.7
C3—C4—H4	119.9	C3'—C2'—C1'	120.90 (16)
C2—C3—C4	120.6 (2)	C3'—C2'—H2'	119.5
C2—C3—H3	119.7	C1'—C2'—H2'	119.5
C4—C3—H3	119.7	C2'—C1'—C6'	118.61 (14)
C3—C2—C1	120.72 (19)	C2'—C1'—C10'	122.20 (14)
C3—C2—H2	119.6	C6'—C1'—C10'	119.19 (15)
C1—C2—H2	119.6	C9'—C10'—C1'	118.46 (14)
C2—C1—C6	118.62 (16)	C9'—C10'—C11'	120.95 (14)
C2—C1—C10	121.92 (16)	C1'—C10'—C11'	120.45 (14)
C6—C1—C10	119.45 (16)	C20'—C11'—C12'	118.91 (15)
C9—C10—C1	118.04 (16)	C20'—C11'—C10'	121.86 (14)
C9—C10—C11	121.39 (15)	C12'—C11'—C10'	119.20 (14)
C1—C10—C11	120.54 (15)	C13'—C12'—C17'	118.49 (15)
C20—C11—C12	118.19 (16)	C13'—C12'—C11'	122.29 (15)
C20—C11—C10	121.70 (15)	C17'—C12'—C11'	119.22 (15)
C12—C11—C10	120.11 (16)	C14'—C13'—C12'	121.00 (17)
C13—C12—C17	119.17 (18)	C14'—C13'—H13'	119.5
C13—C12—C11	121.76 (18)	C12'—C13'—H13'	119.5
C17—C12—C11	119.06 (18)	C13'—C14'—C15'	120.66 (19)
C14—C13—C12	119.9 (2)	C13'—C14'—H14'	119.7
C14—C13—H13	120.1	C15'—C14'—H14'	119.7
C12—C13—H13	120.1	C16'—C15'—C14'	119.78 (18)
C13—C14—C15	120.7 (3)	C16'—C15'—H15'	120.1
C13—C14—H14	119.6	C14'—C15'—H15'	120.1
C15—C14—H14	119.6	C15'—C16'—C17'	121.42 (18)
C16—C15—C14	120.3 (2)	C15'—C16'—H16'	119.3
C16—C15—H15	119.8	C17'—C16'—H16'	119.3
C14—C15—H15	119.8	C16'—C17'—C18'	122.49 (17)
C15—C16—C17	121.3 (2)	C16'—C17'—C12'	118.65 (17)
C15—C16—H16	119.4	C18'—C17'—C12'	118.84 (16)
C17—C16—H16	119.4	C19'—C18'—C17'	121.47 (16)
C18—C17—C16	122.4 (2)	C19'—C18'—H18'	119.3
C18—C17—C12	119.04 (18)	C17'—C18'—H18'	119.3
C16—C17—C12	118.5 (2)	C18'—C19'—C20'	118.98 (17)
C19—C18—C17	121.51 (19)	C18'—C19'—H19'	120.5
C19—C18—H18	119.2	C20'—C19'—H19'	120.5
C17—C18—H18	119.2	C11'—C20'—O1'	116.69 (14)
C18—C19—C20	118.9 (2)	C11'—C20'—C19'	122.58 (16)
C18—C19—H19	120.6	O1'—C20'—C19'	120.55 (15)
C20—C19—H19	120.6	O2'—C21'—O3'	127.56 (17)
C11—C20—C19	123.18 (17)	O2'—C21'—O1'	125.45 (17)
C11—C20—O1	118.07 (15)	O3'—C21'—O1'	106.99 (14)
C19—C20—O1	118.60 (16)	C23'—C22'—O3'	109.51 (18)
O2—C21—O3	128.02 (18)	C23'—C22'—H22C	109.8
O2—C21—O1	125.31 (19)	O3'—C22'—H22C	109.8
O3—C21—O1	106.67 (15)	C23'—C22'—H22D	109.8
C23—C22—O3	114.1 (2)	O3'—C22'—H22D	109.8
C23—C22—H22A	108.7	H22C—C22'—H22D	108.2
O3—C22—H22A	108.7	C22'—C23'—H23D	109.5
C23—C22—H22B	108.7	C22'—C23'—H23E	109.5
O3—C22—H22B	108.7	H23D—C23'—H23E	109.5
H22A—C22—H22B	107.6	C22'—C23'—H23F	109.5
C22—C23—H23A	109.5	H23D—C23'—H23F	109.5
C22—C23—H23B	109.5	H23E—C23'—H23F	109.5
H23A—C23—H23B	109.5	O5'—C24'—O6'	127.66 (16)
C22—C23—H23C	109.5	O5'—C24'—O4'	125.38 (15)
H23A—C23—H23C	109.5	O6'—C24'—O4'	106.96 (14)
H23B—C23—H23C	109.5	O6'—C25'—C26'	111.53 (16)
O5—C24—O6	127.59 (17)	O6'—C25'—H25C	109.3
O5—C24—O4	125.70 (16)	C26'—C25'—H25C	109.3
O6—C24—O4	106.70 (14)	O6'—C25'—H25D	109.3
O6—C25—C26	111.50 (18)	C26'—C25'—H25D	109.3
O6—C25—H25A	109.3	H25C—C25'—H25D	108.0
C26—C25—H25A	109.3	C25'—C26'—H26D	109.5
O6—C25—H25B	109.3	C25'—C26'—H26E	109.5
C26—C25—H25B	109.3	H26D—C26'—H26E	109.5
H25A—C25—H25B	108.0	C25'—C26'—H26F	109.5
C25—C26—H26A	109.5	H26D—C26'—H26F	109.5
C25—C26—H26B	109.5	H26E—C26'—H26F	109.5
H26A—C26—H26B	109.5	C21'—O1'—C20'	117.15 (12)
C25—C26—H26C	109.5	C21'—O3'—C22'	115.02 (15)
H26A—C26—H26C	109.5	C24'—O4'—C9'	115.70 (12)
H26B—C26—H26C	109.5	C21—O3—C22	117.08 (19)
C10'—C9'—C8'	123.11 (15)	C21—O1—C20	116.62 (13)
C10'—C9'—O4'	118.17 (14)	C24'—O6'—C25'	115.63 (14)
C8'—C9'—O4'	118.53 (14)	C24—O4—C9	116.23 (13)
C7'—C8'—C9'	118.78 (16)	C24—O6—C25	115.41 (14)
C10—C9—C8—C7	−1.6 (3)	C7'—C6'—C1'—C10'	−1.4 (2)
O4—C9—C8—C7	−176.59 (16)	C5'—C6'—C1'—C10'	178.88 (14)
C9—C8—C7—C6	0.4 (3)	C8'—C9'—C10'—C1'	−0.8 (2)
C8—C7—C6—C5	−177.62 (18)	O4'—C9'—C10'—C1'	−175.79 (13)
C8—C7—C6—C1	1.0 (3)	C8'—C9'—C10'—C11'	174.86 (15)
C7—C6—C5—C4	178.45 (19)	O4'—C9'—C10'—C11'	−0.1 (2)
C1—C6—C5—C4	−0.2 (3)	C2'—C1'—C10'—C9'	−178.30 (15)
C6—C5—C4—C3	1.4 (3)	C6'—C1'—C10'—C9'	1.8 (2)
C5—C4—C3—C2	−1.3 (3)	C2'—C1'—C10'—C11'	6.0 (2)
C4—C3—C2—C1	−0.2 (3)	C6'—C1'—C10'—C11'	−173.93 (14)
C3—C2—C1—C6	1.4 (3)	C9'—C10'—C11'—C20'	97.87 (19)
C3—C2—C1—C10	−177.09 (17)	C1'—C10'—C11'—C20'	−86.52 (19)
C7—C6—C1—C2	−179.90 (17)	C9'—C10'—C11'—C12'	−84.37 (19)
C5—C6—C1—C2	−1.2 (3)	C1'—C10'—C11'—C12'	91.24 (18)
C7—C6—C1—C10	−1.4 (2)	C20'—C11'—C12'—C13'	178.17 (15)
C5—C6—C1—C10	177.30 (16)	C10'—C11'—C12'—C13'	0.3 (2)
C8—C9—C10—C1	1.2 (3)	C20'—C11'—C12'—C17'	−0.5 (2)
O4—C9—C10—C1	176.23 (14)	C10'—C11'—C12'—C17'	−178.33 (14)
C8—C9—C10—C11	−176.84 (16)	C17'—C12'—C13'—C14'	−0.2 (2)
O4—C9—C10—C11	−1.8 (2)	C11'—C12'—C13'—C14'	−178.90 (16)
C2—C1—C10—C9	178.80 (16)	C12'—C13'—C14'—C15'	−0.2 (3)
C6—C1—C10—C9	0.3 (2)	C13'—C14'—C15'—C16'	0.3 (3)
C2—C1—C10—C11	−3.2 (2)	C14'—C15'—C16'—C17'	0.0 (3)
C6—C1—C10—C11	178.35 (15)	C15'—C16'—C17'—C18'	177.72 (18)
C9—C10—C11—C20	−91.0 (2)	C15'—C16'—C17'—C12'	−0.5 (3)
C1—C10—C11—C20	91.0 (2)	C13'—C12'—C17'—C16'	0.6 (2)
C9—C10—C11—C12	89.9 (2)	C11'—C12'—C17'—C16'	179.28 (14)
C1—C10—C11—C12	−88.1 (2)	C13'—C12'—C17'—C18'	−177.70 (15)
C20—C11—C12—C13	178.97 (16)	C11'—C12'—C17'—C18'	1.0 (2)
C10—C11—C12—C13	−1.9 (2)	C16'—C17'—C18'—C19'	−178.93 (16)
C20—C11—C12—C17	−0.1 (2)	C12'—C17'—C18'—C19'	−0.7 (3)
C10—C11—C12—C17	179.08 (15)	C17'—C18'—C19'—C20'	−0.1 (3)
C17—C12—C13—C14	2.5 (3)	C12'—C11'—C20'—O1'	−175.38 (13)
C11—C12—C13—C14	−176.53 (17)	C10'—C11'—C20'—O1'	2.4 (2)
C12—C13—C14—C15	−0.5 (3)	C12'—C11'—C20'—C19'	−0.3 (2)
C13—C14—C15—C16	−2.1 (3)	C10'—C11'—C20'—C19'	177.44 (15)
C14—C15—C16—C17	2.6 (3)	C18'—C19'—C20'—C11'	0.6 (3)
C15—C16—C17—C18	179.31 (19)	C18'—C19'—C20'—O1'	175.50 (15)
C15—C16—C17—C12	−0.5 (3)	O2'—C21'—O1'—C20'	−7.6 (2)
C13—C12—C17—C18	178.15 (17)	O3'—C21'—O1'—C20'	172.62 (13)
C11—C12—C17—C18	−2.8 (2)	C11'—C20'—O1'—C21'	−121.40 (16)
C13—C12—C17—C16	−2.0 (2)	C19'—C20'—O1'—C21'	63.4 (2)
C11—C12—C17—C16	177.07 (16)	O2'—C21'—O3'—C22'	3.1 (3)
C16—C17—C18—C19	−176.88 (18)	O1'—C21'—O3'—C22'	−177.12 (17)
C12—C17—C18—C19	3.0 (3)	C23'—C22'—O3'—C21'	161.4 (2)
C17—C18—C19—C20	−0.2 (3)	O5'—C24'—O4'—C9'	−8.8 (2)
C12—C11—C20—C19	3.0 (3)	O6'—C24'—O4'—C9'	170.79 (13)
C10—C11—C20—C19	−176.19 (16)	C10'—C9'—O4'—C24'	−91.69 (17)
C12—C11—C20—O1	178.35 (14)	C8'—C9'—O4'—C24'	93.12 (18)
C10—C11—C20—O1	−0.8 (2)	O2—C21—O3—C22	−0.4 (3)
C18—C19—C20—C11	−2.9 (3)	O1—C21—O3—C22	179.06 (19)
C18—C19—C20—O1	−178.24 (16)	C23—C22—O3—C21	−119.3 (4)
C10'—C9'—C8'—C7'	−0.5 (3)	O2—C21—O1—C20	−4.3 (3)
O4'—C9'—C8'—C7'	174.40 (15)	O3—C21—O1—C20	176.18 (14)
C9'—C8'—C7'—C6'	0.9 (3)	C11—C20—O1—C21	119.31 (17)
C8'—C7'—C6'—C5'	179.74 (16)	C19—C20—O1—C21	−65.1 (2)
C8'—C7'—C6'—C1'	0.1 (2)	O5'—C24'—O6'—C25'	−0.9 (3)
C7'—C6'—C5'—C4'	−178.69 (17)	O4'—C24'—O6'—C25'	179.53 (14)
C1'—C6'—C5'—C4'	1.0 (2)	C26'—C25'—O6'—C24'	−78.8 (2)
C6'—C5'—C4'—C3'	0.1 (3)	O5—C24—O4—C9	0.7 (3)
C5'—C4'—C3'—C2'	−1.1 (3)	O6—C24—O4—C9	−179.62 (14)
C4'—C3'—C2'—C1'	1.1 (3)	C10—C9—O4—C24	109.50 (17)
C3'—C2'—C1'—C6'	0.0 (2)	C8—C9—O4—C24	−75.2 (2)
C3'—C2'—C1'—C10'	−179.89 (15)	O5—C24—O6—C25	0.7 (3)
C7'—C6'—C1'—C2'	178.66 (15)	O4—C24—O6—C25	−178.97 (15)
C5'—C6'—C1'—C2'	−1.0 (2)	C26—C25—O6—C24	78.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5′—H5′···O1^i	0.95	2.59	3.519 (2)	165
C7—H7···O2′^ii	0.95	2.57	3.405 (3)	146
C16—H16···O5′^iii	0.95	2.56	3.369 (3)	143

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

(90K) 1,1'-binaphthalene-2,2'-diyl diethyl bis(carbonate)

Crystal data

C26H22O6	Z = 4
Mr = 430.44	F(000) = 904
Triclinic, P1	Dx = 1.350 Mg m^−3
Hall symbol: -P 1	Melting point: 417.67 K
a = 10.7955 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.726 (2) Å	Cell parameters from 667 reflections
c = 15.887 (3) Å	θ = 0.9–28.0°
α = 63.491 (2)°	µ = 0.10 mm^−1
β = 72.400 (2)°	T = 90 K
γ = 73.011 (2)°	Block, colourless
V = 2117.4 (6) Å^3	0.50 × 0.31 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer	8616 independent reflections
Radiation source: fine-focus sealed tube	7378 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ϕ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.946, Tmax = 0.981	k = −18→18
22555 measured reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0477P)^2 + 0.6139P] where P = (Fo^2 + 2Fc^2)/3
8616 reflections	(Δ/σ)max = 0.001
601 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C22	0.7959 (4)	0.8568 (4)	0.5293 (3)	0.0276 (10)	0.585 (10)
H22E	0.8060	0.8981	0.5610	0.033*	0.585 (10)
H22F	0.8466	0.8810	0.4624	0.033*	0.585 (10)
C23	0.8452 (4)	0.7442 (3)	0.5825 (4)	0.0345 (13)	0.585 (10)
H23G	0.7923	0.7208	0.6478	0.052*	0.585 (10)
H23H	0.9380	0.7336	0.5852	0.052*	0.585 (10)
H23I	0.8374	0.7046	0.5491	0.052*	0.585 (10)
C23A	0.8293 (5)	0.7778 (6)	0.6167 (4)	0.0398 (18)	0.415 (10)
H23D	0.8013	0.8347	0.6386	0.060*	0.415 (10)
H23E	0.9244	0.7519	0.6143	0.060*	0.415 (10)
H23F	0.7808	0.7220	0.6614	0.060*	0.415 (10)
C22A	0.8012 (5)	0.8158 (6)	0.5187 (4)	0.0306 (15)	0.415 (10)
H22C	0.8150	0.7579	0.4992	0.037*	0.415 (10)
H22D	0.8581	0.8657	0.4704	0.037*	0.415 (10)
C1	0.20721 (15)	0.77630 (13)	0.59744 (12)	0.0219 (3)
C2	0.12453 (16)	0.87333 (14)	0.58953 (13)	0.0271 (4)
H2	0.1346	0.9315	0.5304	0.033*
C3	0.03050 (17)	0.88369 (16)	0.66642 (14)	0.0351 (4)
H3	−0.0237	0.9492	0.6603	0.042*
C4	0.01330 (18)	0.79860 (16)	0.75426 (14)	0.0369 (5)
H4	−0.0511	0.8072	0.8075	0.044*
C5	0.08831 (17)	0.70397 (15)	0.76358 (13)	0.0323 (4)
H5	0.0741	0.6467	0.8229	0.039*
C6	0.18762 (16)	0.68944 (13)	0.68599 (12)	0.0246 (4)
C7	0.26963 (17)	0.59241 (13)	0.69448 (12)	0.0275 (4)
H7	0.2562	0.5340	0.7530	0.033*
C8	0.36738 (16)	0.58159 (13)	0.62015 (12)	0.0252 (4)
H8	0.4215	0.5161	0.6264	0.030*
C9	0.38743 (15)	0.66821 (13)	0.53430 (11)	0.0210 (3)
C10	0.31070 (15)	0.76401 (12)	0.51998 (11)	0.0192 (3)
C11	0.33177 (15)	0.85305 (12)	0.42564 (11)	0.0200 (3)
C12	0.26192 (16)	0.87375 (13)	0.35337 (12)	0.0243 (4)
C13	0.17506 (17)	0.81067 (15)	0.36689 (14)	0.0310 (4)
H13	0.1572	0.7549	0.4269	0.037*
C14	0.11626 (18)	0.82964 (18)	0.29348 (16)	0.0414 (5)
H14	0.0590	0.7862	0.3030	0.050*
C15	0.14006 (19)	0.91226 (18)	0.20492 (15)	0.0436 (6)
H15	0.1007	0.9235	0.1543	0.052*
C16	0.21920 (18)	0.97647 (17)	0.19113 (13)	0.0383 (5)
H16	0.2320	1.0337	0.1315	0.046*
C17	0.28290 (17)	0.95962 (14)	0.26401 (12)	0.0284 (4)
C18	0.36674 (17)	1.02458 (14)	0.25106 (12)	0.0315 (4)
H18	0.3776	1.0837	0.1928	0.038*
C19	0.43232 (17)	1.00443 (13)	0.32016 (12)	0.0274 (4)
H19	0.4885	1.0487	0.3105	0.033*
C20	0.41536 (15)	0.91693 (12)	0.40607 (11)	0.0210 (3)
C21	0.61483 (16)	0.87553 (12)	0.45709 (12)	0.0255 (4)
C24	0.61102 (16)	0.63978 (12)	0.46244 (11)	0.0201 (3)
C25	0.82829 (17)	0.60976 (15)	0.37653 (13)	0.0313 (4)
H25A	0.8490	0.6547	0.3998	0.038*
H25B	0.8743	0.6269	0.3086	0.038*
C26	0.87755 (17)	0.49884 (15)	0.43522 (13)	0.0341 (4)
H26A	0.8357	0.4828	0.5030	0.051*
H26B	0.9737	0.4871	0.4278	0.051*
H26C	0.8554	0.4542	0.4132	0.051*
C20'	0.13416 (15)	0.60040 (12)	0.11077 (11)	0.0187 (3)
C19'	0.12606 (16)	0.53001 (12)	0.20730 (11)	0.0230 (3)
H19'	0.0710	0.4798	0.2342	0.028*
C18'	0.19902 (16)	0.53532 (13)	0.26157 (11)	0.0240 (4)
H18'	0.1938	0.4883	0.3268	0.029*
C17'	0.28190 (15)	0.60917 (12)	0.22280 (11)	0.0214 (3)
C16'	0.36030 (16)	0.61415 (14)	0.27734 (12)	0.0273 (4)
H16'	0.3549	0.5684	0.3429	0.033*
C15'	0.44313 (17)	0.68335 (15)	0.23734 (13)	0.0305 (4)
H15'	0.4949	0.6856	0.2750	0.037*
C14'	0.45232 (17)	0.75143 (14)	0.14049 (13)	0.0276 (4)
H14'	0.5108	0.7992	0.1129	0.033*
C13'	0.37758 (16)	0.74953 (12)	0.08540 (12)	0.0225 (3)
H13'	0.3843	0.7964	0.0201	0.027*
C12'	0.29059 (15)	0.67849 (12)	0.12468 (11)	0.0184 (3)
C11'	0.21325 (14)	0.67327 (11)	0.06863 (10)	0.0167 (3)
C10'	0.22481 (14)	0.74405 (11)	−0.03459 (10)	0.0157 (3)
C1'	0.31780 (14)	0.71264 (12)	−0.10659 (10)	0.0160 (3)
C2'	0.39285 (15)	0.61133 (12)	−0.08485 (11)	0.0193 (3)
H2'	0.3809	0.5618	−0.0205	0.023*
C3'	0.48238 (15)	0.58382 (13)	−0.15525 (12)	0.0237 (4)
H3'	0.5311	0.5152	−0.1397	0.028*
C4'	0.50275 (16)	0.65655 (14)	−0.25060 (12)	0.0252 (4)
H4'	0.5663	0.6373	−0.2989	0.030*
C5'	0.43166 (16)	0.75451 (13)	−0.27398 (11)	0.0235 (4)
H5'	0.4461	0.8028	−0.3387	0.028*
C6'	0.33666 (15)	0.78551 (12)	−0.20348 (11)	0.0192 (3)
C7'	0.25975 (16)	0.88624 (12)	−0.22613 (11)	0.0229 (3)
H7'	0.2716	0.9350	−0.2908	0.028*
C8'	0.16925 (16)	0.91473 (12)	−0.15734 (12)	0.0223 (3)
H8'	0.1176	0.9824	−0.1736	0.027*
C9'	0.15362 (14)	0.84257 (12)	−0.06214 (11)	0.0179 (3)
C24'	−0.05559 (15)	0.85619 (11)	0.03557 (11)	0.0185 (3)
C22'	−0.25006 (17)	0.63371 (18)	0.01373 (14)	0.0402 (5)
H22A	−0.2887	0.6914	0.0354	0.048*
H22B	−0.2874	0.5722	0.0625	0.048*
C23'	−0.28214 (18)	0.66189 (15)	−0.08012 (14)	0.0356 (4)
H23A	−0.2451	0.7229	−0.1279	0.053*
H23B	−0.3784	0.6772	−0.0739	0.053*
H23C	−0.2442	0.6042	−0.1007	0.053*
C21'	−0.06467 (15)	0.60717 (12)	0.07451 (11)	0.0208 (3)
C25'	−0.25062 (17)	0.86056 (14)	0.15249 (12)	0.0301 (4)
H25C	−0.2750	0.8515	0.2207	0.036*
H25D	−0.2600	0.7972	0.1495	0.036*
C26'	−0.34292 (17)	0.95149 (14)	0.09693 (14)	0.0327 (4)
H26D	−0.3307	1.0147	0.0972	0.049*
H26E	−0.4345	0.9419	0.1268	0.049*
H26F	−0.3238	0.9571	0.0306	0.049*
O1	0.48113 (10)	0.89777 (9)	0.47800 (8)	0.0231 (3)
O2	0.68034 (12)	0.86481 (10)	0.38532 (9)	0.0356 (3)
O3	0.65607 (12)	0.86795 (11)	0.53045 (9)	0.0369 (3)
O4	0.48449 (11)	0.65512 (9)	0.45591 (8)	0.0235 (3)
O5	0.64750 (11)	0.63555 (9)	0.52858 (8)	0.0249 (3)
O6	0.68558 (11)	0.62979 (9)	0.38265 (8)	0.0261 (3)
O4'	0.06850 (10)	0.87497 (8)	0.01032 (8)	0.0210 (2)
O5'	−0.10235 (11)	0.82830 (9)	−0.00620 (8)	0.0231 (3)
O6'	−0.11323 (11)	0.87465 (9)	0.11421 (8)	0.0246 (3)
O1'	0.06884 (10)	0.59305 (8)	0.05039 (8)	0.0206 (2)
O2'	−0.13064 (11)	0.61388 (9)	0.14806 (8)	0.0265 (3)
O3'	−0.10676 (11)	0.61154 (9)	0.00270 (8)	0.0257 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C22	0.0206 (17)	0.028 (2)	0.037 (2)	−0.0067 (16)	−0.0080 (14)	−0.0125 (17)
C23	0.0281 (18)	0.028 (2)	0.051 (3)	−0.0041 (15)	−0.0182 (18)	−0.0125 (18)
C23A	0.026 (3)	0.060 (4)	0.042 (3)	−0.006 (2)	−0.008 (2)	−0.029 (3)
C22A	0.016 (2)	0.042 (4)	0.039 (3)	−0.005 (3)	−0.0024 (19)	−0.022 (3)
C1	0.0164 (8)	0.0290 (9)	0.0225 (8)	−0.0069 (7)	−0.0019 (6)	−0.0116 (7)
C2	0.0217 (8)	0.0315 (9)	0.0259 (9)	−0.0046 (7)	−0.0002 (7)	−0.0123 (8)
C3	0.0229 (9)	0.0451 (11)	0.0364 (11)	−0.0037 (8)	0.0036 (8)	−0.0230 (9)
C4	0.0237 (9)	0.0585 (13)	0.0305 (10)	−0.0139 (9)	0.0099 (8)	−0.0251 (10)
C5	0.0263 (9)	0.0469 (11)	0.0228 (9)	−0.0196 (8)	0.0029 (7)	−0.0101 (8)
C6	0.0200 (8)	0.0329 (9)	0.0235 (9)	−0.0128 (7)	−0.0027 (7)	−0.0094 (7)
C7	0.0297 (9)	0.0277 (9)	0.0237 (9)	−0.0156 (7)	−0.0074 (7)	−0.0013 (7)
C8	0.0254 (9)	0.0209 (8)	0.0320 (9)	−0.0059 (7)	−0.0110 (7)	−0.0085 (7)
C9	0.0172 (8)	0.0268 (8)	0.0240 (8)	−0.0040 (6)	−0.0044 (6)	−0.0142 (7)
C10	0.0167 (7)	0.0245 (8)	0.0200 (8)	−0.0053 (6)	−0.0045 (6)	−0.0102 (7)
C11	0.0175 (8)	0.0223 (8)	0.0177 (8)	0.0028 (6)	−0.0016 (6)	−0.0110 (7)
C12	0.0191 (8)	0.0308 (9)	0.0243 (9)	0.0076 (7)	−0.0055 (7)	−0.0187 (7)
C13	0.0226 (9)	0.0388 (10)	0.0364 (10)	0.0039 (8)	−0.0089 (8)	−0.0230 (9)
C14	0.0248 (10)	0.0602 (14)	0.0569 (14)	0.0079 (9)	−0.0162 (9)	−0.0429 (12)
C15	0.0312 (11)	0.0688 (15)	0.0392 (12)	0.0220 (10)	−0.0198 (9)	−0.0394 (12)
C16	0.0315 (10)	0.0534 (12)	0.0243 (9)	0.0189 (9)	−0.0112 (8)	−0.0232 (9)
C17	0.0244 (9)	0.0353 (10)	0.0207 (8)	0.0115 (7)	−0.0057 (7)	−0.0165 (8)
C18	0.0308 (10)	0.0294 (9)	0.0188 (8)	0.0040 (8)	0.0018 (7)	−0.0063 (7)
C19	0.0269 (9)	0.0256 (9)	0.0226 (9)	−0.0031 (7)	0.0025 (7)	−0.0092 (7)
C20	0.0196 (8)	0.0247 (8)	0.0165 (8)	−0.0020 (6)	0.0016 (6)	−0.0107 (7)
C21	0.0204 (8)	0.0205 (8)	0.0233 (9)	−0.0050 (7)	0.0011 (7)	−0.0009 (7)
C24	0.0240 (8)	0.0179 (8)	0.0190 (8)	−0.0042 (6)	−0.0038 (6)	−0.0079 (6)
C25	0.0245 (9)	0.0477 (11)	0.0256 (9)	−0.0105 (8)	0.0040 (7)	−0.0211 (9)
C26	0.0213 (9)	0.0533 (12)	0.0319 (10)	−0.0030 (8)	−0.0046 (7)	−0.0232 (9)
C20'	0.0170 (7)	0.0203 (8)	0.0186 (8)	0.0006 (6)	−0.0017 (6)	−0.0112 (6)
C19'	0.0195 (8)	0.0212 (8)	0.0210 (8)	−0.0041 (6)	0.0036 (6)	−0.0066 (7)
C18'	0.0211 (8)	0.0260 (9)	0.0152 (8)	0.0016 (7)	0.0003 (6)	−0.0059 (7)
C17'	0.0178 (8)	0.0254 (8)	0.0177 (8)	0.0054 (6)	−0.0019 (6)	−0.0125 (7)
C16'	0.0220 (8)	0.0381 (10)	0.0182 (8)	0.0065 (7)	−0.0066 (7)	−0.0138 (8)
C15'	0.0236 (9)	0.0458 (11)	0.0295 (9)	0.0036 (8)	−0.0115 (7)	−0.0234 (9)
C14'	0.0232 (9)	0.0321 (9)	0.0344 (10)	−0.0016 (7)	−0.0087 (7)	−0.0193 (8)
C13'	0.0218 (8)	0.0242 (8)	0.0232 (8)	−0.0010 (7)	−0.0051 (7)	−0.0122 (7)
C12'	0.0164 (7)	0.0205 (8)	0.0181 (8)	0.0025 (6)	−0.0020 (6)	−0.0118 (7)
C11'	0.0142 (7)	0.0174 (7)	0.0162 (7)	0.0014 (6)	0.0003 (6)	−0.0094 (6)
C10'	0.0135 (7)	0.0189 (7)	0.0162 (7)	−0.0043 (6)	−0.0029 (6)	−0.0074 (6)
C1'	0.0133 (7)	0.0216 (8)	0.0158 (7)	−0.0055 (6)	−0.0029 (6)	−0.0082 (6)
C2'	0.0184 (8)	0.0219 (8)	0.0168 (8)	−0.0024 (6)	−0.0030 (6)	−0.0081 (6)
C3'	0.0185 (8)	0.0296 (9)	0.0267 (9)	0.0009 (7)	−0.0047 (7)	−0.0174 (7)
C4'	0.0169 (8)	0.0406 (10)	0.0223 (8)	−0.0050 (7)	0.0012 (6)	−0.0194 (8)
C5'	0.0208 (8)	0.0362 (10)	0.0147 (8)	−0.0114 (7)	0.0000 (6)	−0.0096 (7)
C6'	0.0163 (7)	0.0251 (8)	0.0188 (8)	−0.0078 (6)	−0.0032 (6)	−0.0086 (7)
C7'	0.0257 (8)	0.0231 (8)	0.0172 (8)	−0.0086 (7)	−0.0059 (7)	−0.0020 (7)
C8'	0.0230 (8)	0.0170 (8)	0.0272 (9)	−0.0014 (6)	−0.0097 (7)	−0.0075 (7)
C9'	0.0150 (7)	0.0214 (8)	0.0213 (8)	−0.0023 (6)	−0.0038 (6)	−0.0125 (7)
C24'	0.0220 (8)	0.0139 (7)	0.0169 (8)	−0.0002 (6)	−0.0040 (6)	−0.0055 (6)
C22'	0.0192 (9)	0.0701 (15)	0.0418 (11)	−0.0152 (9)	0.0010 (8)	−0.0313 (11)
C23'	0.0248 (9)	0.0378 (11)	0.0446 (11)	−0.0038 (8)	−0.0094 (8)	−0.0161 (9)
C21'	0.0210 (8)	0.0182 (8)	0.0232 (8)	−0.0088 (6)	0.0013 (7)	−0.0087 (7)
C25'	0.0308 (10)	0.0341 (10)	0.0255 (9)	−0.0129 (8)	0.0091 (7)	−0.0169 (8)
C26'	0.0231 (9)	0.0394 (11)	0.0399 (11)	−0.0081 (8)	0.0036 (8)	−0.0242 (9)
O1	0.0186 (6)	0.0299 (6)	0.0206 (6)	−0.0069 (5)	−0.0001 (5)	−0.0107 (5)
O2	0.0280 (7)	0.0344 (7)	0.0256 (7)	−0.0002 (5)	0.0059 (5)	−0.0062 (6)
O3	0.0197 (6)	0.0534 (9)	0.0286 (7)	−0.0088 (6)	−0.0056 (5)	−0.0066 (6)
O4	0.0222 (6)	0.0281 (6)	0.0235 (6)	0.0017 (5)	−0.0073 (5)	−0.0152 (5)
O5	0.0225 (6)	0.0375 (7)	0.0198 (6)	−0.0105 (5)	−0.0005 (5)	−0.0151 (5)
O6	0.0254 (6)	0.0348 (7)	0.0206 (6)	−0.0009 (5)	−0.0030 (5)	−0.0170 (5)
O4'	0.0170 (5)	0.0236 (6)	0.0265 (6)	0.0015 (4)	−0.0043 (5)	−0.0167 (5)
O5'	0.0225 (6)	0.0278 (6)	0.0222 (6)	−0.0083 (5)	0.0001 (5)	−0.0131 (5)
O6'	0.0256 (6)	0.0284 (6)	0.0212 (6)	−0.0032 (5)	0.0000 (5)	−0.0150 (5)
O1'	0.0181 (5)	0.0250 (6)	0.0212 (6)	−0.0060 (5)	0.0003 (4)	−0.0127 (5)
O2'	0.0223 (6)	0.0326 (7)	0.0221 (6)	−0.0083 (5)	0.0035 (5)	−0.0116 (5)
O3'	0.0182 (6)	0.0356 (7)	0.0305 (6)	−0.0082 (5)	−0.0003 (5)	−0.0202 (6)

Geometric parameters (Å, º)

C22—O3	1.466 (4)	C26—H26C	0.9800
C22—C23	1.501 (6)	C20'—C11'	1.370 (2)
C23A—C22A	1.496 (9)	C20'—O1'	1.4056 (18)
C23A—H23D	0.9800	C20'—C19'	1.410 (2)
C23A—H23E	0.9800	C19'—C18'	1.370 (2)
C23A—H23F	0.9800	C19'—H19'	0.9500
C22A—O3	1.525 (6)	C18'—C17'	1.414 (2)
C22A—H22C	0.9900	C18'—H18'	0.9500
C22A—H22D	0.9900	C17'—C16'	1.417 (2)
C1—C2	1.420 (2)	C17'—C12'	1.424 (2)
C1—C6	1.425 (2)	C16'—C15'	1.361 (3)
C1—C10	1.430 (2)	C16'—H16'	0.9500
C2—C3	1.368 (2)	C15'—C14'	1.404 (3)
C2—H2	0.9500	C15'—H15'	0.9500
C3—C4	1.404 (3)	C14'—C13'	1.371 (2)
C3—H3	0.9500	C14'—H14'	0.9500
C4—C5	1.360 (3)	C13'—C12'	1.415 (2)
C4—H4	0.9500	C13'—H13'	0.9500
C5—C6	1.420 (2)	C12'—C11'	1.430 (2)
C5—H5	0.9500	C11'—C10'	1.489 (2)
C6—C7	1.416 (2)	C10'—C9'	1.368 (2)
C7—C8	1.360 (2)	C10'—C1'	1.427 (2)
C7—H7	0.9500	C1'—C2'	1.416 (2)
C8—C9	1.401 (2)	C1'—C6'	1.423 (2)
C8—H8	0.9500	C2'—C3'	1.368 (2)
C9—C10	1.368 (2)	C2'—H2'	0.9500
C9—O4	1.4118 (18)	C3'—C4'	1.406 (2)
C10—C11	1.494 (2)	C3'—H3'	0.9500
C11—C20	1.364 (2)	C4'—C5'	1.362 (2)
C11—C12	1.434 (2)	C4'—H4'	0.9500
C12—C13	1.413 (3)	C5'—C6'	1.415 (2)
C12—C17	1.427 (2)	C5'—H5'	0.9500
C13—C14	1.376 (3)	C6'—C7'	1.416 (2)
C13—H13	0.9500	C7'—C8'	1.360 (2)
C14—C15	1.401 (3)	C7'—H7'	0.9500
C14—H14	0.9500	C8'—C9'	1.400 (2)
C15—C16	1.359 (3)	C8'—H8'	0.9500
C15—H15	0.9500	C9'—O4'	1.4113 (18)
C16—C17	1.414 (2)	C24'—O5'	1.1963 (18)
C16—H16	0.9500	C24'—O6'	1.3252 (18)
C17—C18	1.412 (3)	C24'—O4'	1.3506 (19)
C18—C19	1.361 (2)	C22'—O3'	1.457 (2)
C18—H18	0.9500	C22'—C23'	1.480 (3)
C19—C20	1.405 (2)	C22'—H22A	0.9900
C19—H19	0.9500	C22'—H22B	0.9900
C20—O1	1.4056 (19)	C23'—H23A	0.9800
C21—O2	1.197 (2)	C23'—H23B	0.9800
C21—O3	1.318 (2)	C23'—H23C	0.9800
C21—O1	1.3534 (19)	C21'—O2'	1.2004 (19)
C24—O5	1.2003 (18)	C21'—O3'	1.3201 (19)
C24—O6	1.3253 (18)	C21'—O1'	1.3526 (18)
C24—O4	1.3461 (19)	C25'—O6'	1.461 (2)
C25—O6	1.463 (2)	C25'—C26'	1.504 (3)
C25—C26	1.501 (3)	C25'—H25C	0.9900
C25—H25A	0.9900	C25'—H25D	0.9900
C25—H25B	0.9900	C26'—H26D	0.9800
C26—H26A	0.9800	C26'—H26E	0.9800
C26—H26B	0.9800	C26'—H26F	0.9800
O3—C22—C23	106.8 (3)	C18'—C19'—H19'	120.6
C22A—C23A—H23D	109.5	C20'—C19'—H19'	120.6
C22A—C23A—H23E	109.5	C19'—C18'—C17'	121.53 (15)
H23D—C23A—H23E	109.5	C19'—C18'—H18'	119.2
C22A—C23A—H23F	109.5	C17'—C18'—H18'	119.2
H23D—C23A—H23F	109.5	C18'—C17'—C16'	122.22 (15)
H23E—C23A—H23F	109.5	C18'—C17'—C12'	118.94 (14)
C23A—C22A—O3	103.3 (5)	C16'—C17'—C12'	118.81 (15)
C23A—C22A—H22C	111.1	C15'—C16'—C17'	121.12 (16)
O3—C22A—H22C	111.1	C15'—C16'—H16'	119.4
C23A—C22A—H22D	111.1	C17'—C16'—H16'	119.4
O3—C22A—H22D	111.1	C16'—C15'—C14'	120.17 (16)
H22C—C22A—H22D	109.1	C16'—C15'—H15'	119.9
C2—C1—C6	118.74 (15)	C14'—C15'—H15'	119.9
C2—C1—C10	121.89 (15)	C13'—C14'—C15'	120.54 (16)
C6—C1—C10	119.37 (15)	C13'—C14'—H14'	119.7
C3—C2—C1	120.51 (17)	C15'—C14'—H14'	119.7
C3—C2—H2	119.7	C14'—C13'—C12'	120.76 (16)
C1—C2—H2	119.7	C14'—C13'—H13'	119.6
C2—C3—C4	120.70 (18)	C12'—C13'—H13'	119.6
C2—C3—H3	119.7	C13'—C12'—C17'	118.61 (14)
C4—C3—H3	119.7	C13'—C12'—C11'	122.09 (14)
C5—C4—C3	120.34 (16)	C17'—C12'—C11'	119.30 (14)
C5—C4—H4	119.8	C20'—C11'—C12'	118.83 (14)
C3—C4—H4	119.8	C20'—C11'—C10'	121.84 (13)
C4—C5—C6	121.03 (17)	C12'—C11'—C10'	119.28 (13)
C4—C5—H5	119.5	C9'—C10'—C1'	118.44 (13)
C6—C5—H5	119.5	C9'—C10'—C11'	121.08 (13)
C7—C6—C5	122.24 (16)	C1'—C10'—C11'	120.33 (13)
C7—C6—C1	119.10 (15)	C2'—C1'—C6'	118.71 (13)
C5—C6—C1	118.64 (16)	C2'—C1'—C10'	122.18 (13)
C8—C7—C6	120.99 (15)	C6'—C1'—C10'	119.11 (13)
C8—C7—H7	119.5	C3'—C2'—C1'	120.85 (15)
C6—C7—H7	119.5	C3'—C2'—H2'	119.6
C7—C8—C9	119.25 (16)	C1'—C2'—H2'	119.6
C7—C8—H8	120.4	C2'—C3'—C4'	120.33 (15)
C9—C8—H8	120.4	C2'—C3'—H3'	119.8
C10—C9—C8	123.17 (15)	C4'—C3'—H3'	119.8
C10—C9—O4	117.86 (14)	C5'—C4'—C3'	120.26 (14)
C8—C9—O4	118.78 (14)	C5'—C4'—H4'	119.9
C9—C10—C1	118.10 (15)	C3'—C4'—H4'	119.9
C9—C10—C11	121.28 (14)	C4'—C5'—C6'	121.10 (15)
C1—C10—C11	120.60 (14)	C4'—C5'—H5'	119.5
C20—C11—C12	118.39 (15)	C6'—C5'—H5'	119.5
C20—C11—C10	121.72 (14)	C5'—C6'—C7'	122.25 (15)
C12—C11—C10	119.89 (14)	C5'—C6'—C1'	118.73 (14)
C13—C12—C17	118.84 (16)	C7'—C6'—C1'	119.02 (14)
C13—C12—C11	122.20 (16)	C8'—C7'—C6'	121.41 (15)
C17—C12—C11	118.94 (16)	C8'—C7'—H7'	119.3
C14—C13—C12	120.28 (19)	C6'—C7'—H7'	119.3
C14—C13—H13	119.9	C7'—C8'—C9'	118.78 (14)
C12—C13—H13	119.9	C7'—C8'—H8'	120.6
C13—C14—C15	120.7 (2)	C9'—C8'—H8'	120.6
C13—C14—H14	119.7	C10'—C9'—C8'	123.20 (14)
C15—C14—H14	119.7	C10'—C9'—O4'	117.92 (13)
C16—C15—C14	120.28 (18)	C8'—C9'—O4'	118.67 (13)
C16—C15—H15	119.9	O5'—C24'—O6'	127.60 (15)
C14—C15—H15	119.9	O5'—C24'—O4'	125.62 (14)
C15—C16—C17	121.14 (19)	O6'—C24'—O4'	106.77 (13)
C15—C16—H16	119.4	O3'—C22'—C23'	108.48 (15)
C17—C16—H16	119.4	O3'—C22'—H22A	110.0
C18—C17—C16	122.21 (18)	C23'—C22'—H22A	110.0
C18—C17—C12	119.09 (15)	O3'—C22'—H22B	110.0
C16—C17—C12	118.70 (18)	C23'—C22'—H22B	110.0
C19—C18—C17	121.46 (16)	H22A—C22'—H22B	108.4
C19—C18—H18	119.3	C22'—C23'—H23A	109.5
C17—C18—H18	119.3	C22'—C23'—H23B	109.5
C18—C19—C20	118.77 (17)	H23A—C23'—H23B	109.5
C18—C19—H19	120.6	C22'—C23'—H23C	109.5
C20—C19—H19	120.6	H23A—C23'—H23C	109.5
C11—C20—O1	118.16 (14)	H23B—C23'—H23C	109.5
C11—C20—C19	123.23 (15)	O2'—C21'—O3'	127.34 (15)
O1—C20—C19	118.48 (14)	O2'—C21'—O1'	125.53 (15)
O2—C21—O3	127.91 (16)	O3'—C21'—O1'	107.13 (12)
O2—C21—O1	125.41 (17)	O6'—C25'—C26'	111.38 (14)
O3—C21—O1	106.69 (14)	O6'—C25'—H25C	109.4
O5—C24—O6	127.41 (15)	C26'—C25'—H25C	109.4
O5—C24—O4	125.91 (14)	O6'—C25'—H25D	109.4
O6—C24—O4	106.68 (13)	C26'—C25'—H25D	109.4
O6—C25—C26	111.27 (14)	H25C—C25'—H25D	108.0
O6—C25—H25A	109.4	C25'—C26'—H26D	109.5
C26—C25—H25A	109.4	C25'—C26'—H26E	109.5
O6—C25—H25B	109.4	H26D—C26'—H26E	109.5
C26—C25—H25B	109.4	C25'—C26'—H26F	109.5
H25A—C25—H25B	108.0	H26D—C26'—H26F	109.5
C25—C26—H26A	109.5	H26E—C26'—H26F	109.5
C25—C26—H26B	109.5	C21—O1—C20	116.63 (12)
H26A—C26—H26B	109.5	C21—O3—C22	122.7 (2)
C25—C26—H26C	109.5	C21—O3—C22A	105.9 (3)
H26A—C26—H26C	109.5	C24—O4—C9	116.05 (12)
H26B—C26—H26C	109.5	C24—O6—C25	115.36 (12)
C11'—C20'—O1'	116.40 (13)	C24'—O4'—C9'	115.28 (11)
C11'—C20'—C19'	122.64 (14)	C24'—O6'—C25'	115.38 (12)
O1'—C20'—C19'	120.75 (14)	C21'—O1'—C20'	116.82 (11)
C18'—C19'—C20'	118.76 (15)	C21'—O3'—C22'	114.58 (13)
C6—C1—C2—C3	1.9 (2)	C19'—C20'—C11'—C12'	−0.1 (2)
C10—C1—C2—C3	−176.85 (16)	O1'—C20'—C11'—C10'	2.6 (2)
C1—C2—C3—C4	−0.5 (3)	C19'—C20'—C11'—C10'	177.38 (14)
C2—C3—C4—C5	−1.3 (3)	C13'—C12'—C11'—C20'	178.05 (14)
C3—C4—C5—C6	1.6 (3)	C17'—C12'—C11'—C20'	−0.9 (2)
C4—C5—C6—C7	178.21 (16)	C13'—C12'—C11'—C10'	0.5 (2)
C4—C5—C6—C1	−0.2 (3)	C17'—C12'—C11'—C10'	−178.53 (13)
C2—C1—C6—C7	179.99 (15)	C20'—C11'—C10'—C9'	98.58 (18)
C10—C1—C6—C7	−1.2 (2)	C12'—C11'—C10'—C9'	−83.91 (18)
C2—C1—C6—C5	−1.6 (2)	C20'—C11'—C10'—C1'	−85.88 (18)
C10—C1—C6—C5	177.21 (14)	C12'—C11'—C10'—C1'	91.64 (17)
C5—C6—C7—C8	−177.41 (16)	C9'—C10'—C1'—C2'	−178.18 (14)
C1—C6—C7—C8	1.0 (2)	C11'—C10'—C1'—C2'	6.2 (2)
C6—C7—C8—C9	0.5 (2)	C9'—C10'—C1'—C6'	2.2 (2)
C7—C8—C9—C10	−1.8 (2)	C11'—C10'—C1'—C6'	−173.44 (13)
C7—C8—C9—O4	−176.70 (14)	C6'—C1'—C2'—C3'	0.4 (2)
C8—C9—C10—C1	1.5 (2)	C10'—C1'—C2'—C3'	−179.24 (14)
O4—C9—C10—C1	176.45 (13)	C1'—C2'—C3'—C4'	0.9 (2)
C8—C9—C10—C11	−177.10 (14)	C2'—C3'—C4'—C5'	−1.2 (2)
O4—C9—C10—C11	−2.2 (2)	C3'—C4'—C5'—C6'	0.3 (2)
C2—C1—C10—C9	178.75 (15)	C4'—C5'—C6'—C7'	−178.82 (15)
C6—C1—C10—C9	0.0 (2)	C4'—C5'—C6'—C1'	1.0 (2)
C2—C1—C10—C11	−2.6 (2)	C2'—C1'—C6'—C5'	−1.3 (2)
C6—C1—C10—C11	178.66 (14)	C10'—C1'—C6'—C5'	178.30 (13)
C9—C10—C11—C20	−90.40 (19)	C2'—C1'—C6'—C7'	178.53 (14)
C1—C10—C11—C20	91.01 (19)	C10'—C1'—C6'—C7'	−1.9 (2)
C9—C10—C11—C12	90.36 (18)	C5'—C6'—C7'—C8'	−179.76 (15)
C1—C10—C11—C12	−88.23 (18)	C1'—C6'—C7'—C8'	0.4 (2)
C20—C11—C12—C13	178.96 (15)	C6'—C7'—C8'—C9'	0.7 (2)
C10—C11—C12—C13	−1.8 (2)	C1'—C10'—C9'—C8'	−1.2 (2)
C20—C11—C12—C17	0.3 (2)	C11'—C10'—C9'—C8'	174.44 (14)
C10—C11—C12—C17	179.59 (14)	C1'—C10'—C9'—O4'	−175.83 (12)
C17—C12—C13—C14	2.6 (2)	C11'—C10'—C9'—O4'	−0.2 (2)
C11—C12—C13—C14	−176.01 (15)	C7'—C8'—C9'—C10'	−0.3 (2)
C12—C13—C14—C15	−0.8 (3)	C7'—C8'—C9'—O4'	174.33 (13)
C13—C14—C15—C16	−1.6 (3)	O2—C21—O1—C20	−4.8 (2)
C14—C15—C16—C17	2.3 (3)	O3—C21—O1—C20	175.49 (13)
C15—C16—C17—C18	179.30 (16)	C11—C20—O1—C21	118.62 (15)
C15—C16—C17—C12	−0.4 (2)	C19—C20—O1—C21	−65.38 (19)
C13—C12—C17—C18	178.27 (15)	O2—C21—O3—C22	7.9 (4)
C11—C12—C17—C18	−3.1 (2)	O1—C21—O3—C22	−172.4 (3)
C13—C12—C17—C16	−2.0 (2)	O2—C21—O3—C22A	−14.2 (4)
C11—C12—C17—C16	176.69 (14)	O1—C21—O3—C22A	165.5 (3)
C16—C17—C18—C19	−176.76 (16)	C23—C22—O3—C21	−99.4 (4)
C12—C17—C18—C19	3.0 (2)	C23—C22—O3—C22A	−44.0 (7)
C17—C18—C19—C20	−0.1 (2)	C23A—C22A—O3—C21	−161.8 (6)
C12—C11—C20—O1	178.49 (13)	C23A—C22A—O3—C22	64.3 (8)
C10—C11—C20—O1	−0.8 (2)	O5—C24—O4—C9	0.6 (2)
C12—C11—C20—C19	2.7 (2)	O6—C24—O4—C9	−179.78 (12)
C10—C11—C20—C19	−176.57 (14)	C10—C9—O4—C24	110.39 (16)
C18—C19—C20—C11	−2.9 (2)	C8—C9—O4—C24	−74.46 (18)
C18—C19—C20—O1	−178.64 (14)	O5—C24—O6—C25	1.0 (2)
C11'—C20'—C19'—C18'	0.7 (2)	O4—C24—O6—C25	−178.53 (13)
O1'—C20'—C19'—C18'	175.27 (13)	C26—C25—O6—C24	78.16 (17)
C20'—C19'—C18'—C17'	−0.2 (2)	O5'—C24'—O4'—C9'	−10.6 (2)
C19'—C18'—C17'—C16'	−178.53 (14)	O6'—C24'—O4'—C9'	169.40 (12)
C19'—C18'—C17'—C12'	−0.8 (2)	C10'—C9'—O4'—C24'	−89.04 (16)
C18'—C17'—C16'—C15'	177.45 (15)	C8'—C9'—O4'—C24'	96.07 (16)
C12'—C17'—C16'—C15'	−0.3 (2)	O5'—C24'—O6'—C25'	−1.1 (2)
C17'—C16'—C15'—C14'	0.0 (3)	O4'—C24'—O6'—C25'	178.88 (12)
C16'—C15'—C14'—C13'	0.4 (3)	C26'—C25'—O6'—C24'	−78.88 (17)
C15'—C14'—C13'—C12'	−0.5 (2)	O2'—C21'—O1'—C20'	−8.8 (2)
C14'—C13'—C12'—C17'	0.2 (2)	O3'—C21'—O1'—C20'	171.44 (12)
C14'—C13'—C12'—C11'	−178.78 (14)	C11'—C20'—O1'—C21'	−121.79 (14)
C18'—C17'—C12'—C13'	−177.61 (14)	C19'—C20'—O1'—C21'	63.36 (18)
C16'—C17'—C12'—C13'	0.2 (2)	O2'—C21'—O3'—C22'	4.3 (2)
C18'—C17'—C12'—C11'	1.4 (2)	O1'—C21'—O3'—C22'	−176.00 (14)
C16'—C17'—C12'—C11'	179.19 (13)	C23'—C22'—O3'—C21'	166.07 (15)
O1'—C20'—C11'—C12'	−174.90 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5′—H5′···O1^i	0.95	2.57	3.497 (2)	166
C7—H7···O2′^ii	0.95	2.54	3.369 (3)	146
C16—H16···O5′^iii	0.95	2.54	3.327 (3)	140

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