Hydro­gen bonding and C—H...O interactions in 2-[1-(1-naphthyl)ethyl]benzoic acid at 150 K

The title acid, C₁₉H₁₆O₂, crystallized in the centrosymmetric space group Pnna with three mol­ecules in the asymmetric unit (apparently the first reported instance of Z′ = 3 in this space group). Four intermolecular hydrogen bonds have O_D...O_A distances of 2.660 (2), 2.594 (2), 2.633 (2) and 2.646 (2) Å, and angles of 177 (2), 179 (2), 175 (2) and 175 (2)°. The four hydrogen bonds form two R(8) cyclic dimers, one about a twofold axis. Five leading intermolecular C—H...O interactions are present. Although first- and second-level graph sets involving these nine interactions are dominated by finite patterns, a three-dimensional network becomes evident upon analysis of higher-level graphs. A number of intramolecular C—H...O interactions are also present.

S1. Comment

This report is one of a series on hydrogen bonding and C—H···O interactions in carboxylic acids. The title acid, (I), crystallized in the centrosymmetric space group Pnna with three molecules in the asymmetric unit. Four hydrogen bonds and five leading intermolecular C—H···O interactions (Taylor & Kennard, 1982; Steiner & Desiraju, 1998) are present in this structure. The geometric parameters of these are given in Table 2. The three crystallographically inequivalent molecules, shown in Fig. 1, are linked directly to five, three and three neighbors, respectively, by the tabulated interactions. The results of basic first- and second-level graph-set analysis (Bernstein et al., 1995) involving these interactions, labelled a-i for this purpose in the order of their appearance in Table 2, are given in Table 3. \sch

The hydrogen bonds in (I) form two R₂²(8) cyclic dimers. One of these involves one of the independent molecules and a partner which is related by a twofold axis, while the other involves the remaining two independent molecules. Thus, although the space group includes a center of symmetry, it is not involved in formation of the cyclic dimers. Since the twofold axis apposes O1 and O2 with their respective transforms, the hydrogen bonds between them must be either `symmetric disordered' or `symmetric centered' (terminology of Olovsson & Jönsson, 1976). Fixing H1O1 and H1O2 off the twofold axis models them as disordered. However, fixing H1O1 and H1O2 on the twofold axis would produce insignificant changes in any parameters except the O—H distances involving H1O1 and H1O2, and is an equally satisfactory model consistent with the present data. A number of such cases for short hydrogen bonds are tabulated by Olovsson & Jönsson (1976).

As expected due to the presence of three independent molecules, finite graphs predominate in the first- and second-level graph-sets. In the third- and fourth-level sets, however, there are, e.g., three chain patterns which propagate variously along [013], [010] and [101], thus generating a three-dimensional network of interactions. Each of these chains contains the three independent molecules and, respectively, involves interactions efg, iefg and gcei. Of course, the first- and second-level chains given in Table 3, which involve only one of the independent molecules and propagate along [100] and [101], enhance the connectivity of the interaction network.

The geometric parameters of eight leading intramolecular C—H···O interactions are also given in Table 2. These interactions are quite similar for the three inequivalent molecules and doubtless participate in determining the dihedral angles of the carboxyl groups with respect to the planes of the attached benzene rings, which angles are also quite similar as they range from 24.3 (2) to 35.4 (2)°.

In (I) the maximum deviations of atoms from the best-fit planes describing the benzene and naphthalene rings are 0.013 (2) and 0.054 (2) Å, respectively. The benzene and naphthalene ring planes are nearly perpendicular in each molecule.

Selected bond distances and angles in (I) are given in Table 1. Consistent with the recognition that O—H distances in hydrogen bonds which involve symmetry elements such as centers or twofold axes can be unusually long, all distances and angles fall within normal limits. Corresponding C—C bond distances in the three independent molecules are in very good agreement: the largest of the three r.m.s. differences within 21 pairs of corresponding distances is 0.005 (2) Å, while the s.u.s of the individual values are uniformly 0.002 Å. In (I) the closest intermolecular approaches, excluding pairs of atoms involved in the hydrogen-bonding groups or the tabulated C—H···O interactions, are between H6 and H9B^vi [symmetry code: (vi) 1/2 + x, y, 1 − z] and fall short of the corresponding Bondi (1964) van der Waals radius sum by 0.16 Å.

A search of the Cambridge Structural Database (Allen & Kennard, 1993) revealed that this structure is the first example having Z' = 3 in Pnna, and the first organic structure having Z' > 1 in Pnna. Four organometallic structures having Z' = 1.5 or 2 have previously been reported in this space group (refs?).

S2. Experimental

Compound (I) was obtained from a coarsely crystalline sample in the chemical collection of Dr M. S. Newman. An irregular hexagonal slab was cut to provide the experimental sample. A synthesis is described by Newman & Cunico (1972).

S3. Refinement

Difference Fourier methods were used to locate initial H-atom positions, excepting the half-occupancy atoms H1O1 and H1O2, and all these H atoms were refined. The 45 refined C—H distances ranged from 0.93 (2) to 1.07 (2) Å, with a mean value of 0.99 (5) Å; their U_iso values ranged from 0.7 to 1.5 times the U_eq values of the attached C atoms. The 33 ring-H atoms were then made canonical, with C—H = 0.98 Å and U_iso(H) = 1.2 × U_eq(C). Subsequently, the half-occupancy atoms H1O1 and H1O2 were located on a difference map on a twofold axis. They were then fixed 0.1 Å off this axis, along the rays between O1 and O2 and the axis sites, to have them recognized as bonded to O1 and O2; their U_iso values were fixed consistently with the U_iso values of the refined carboxyl-H atoms.

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1992-1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN and PLATON (Spek, 1990).

Figures

Fig. 1. The three independent molecules of compound (I), showing the atom-labeling scheme, with displacement ellipsoids at the 50% probability level. Half-occupancy H atoms are shaded.

(I)

Crystal data

C19H16O2	F(000) = 3504
Mr = 276.33	Dx = 1.263 Mg m^−3
Orthorhombic, Pnna	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2bc	Cell parameters from 91848 reflections
a = 16.8468 (3) Å	θ = 1.2–27.5°
b = 37.3753 (7) Å	µ = 0.08 mm^−1
c = 13.8418 (3) Å	T = 150 K
V = 8715.5 (7) Å^3	Cut irregular hexagonal slab, colorless
Z = 24	0.31 × 0.31 × 0.27 mm

Data collection

Nonius KappaCCD diffractometer	6788 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.046
Graphite monochromator	θmax = 27.5°
ω scans with κ offsets	h = −21→20
91848 measured reflections	k = −48→47
9954 independent reflections	l = −17→17

Refinement

Refinement on F^2	624 parameters
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	Weighting scheme based on measured s.u.'s 1/[σ^2cs + (0.016 I)^2]
wR(F^2) = 0.076	(Δ/σ)max = 0.001
S = 1.67	Δρmax = 0.54 e Å^−3
9951 reflections	Δρmin = −0.44 e Å^−3

Special details

Experimental. The Laue group assignment, the systematic absences and the centrosymmetry indicated by the intensity statistics led uniquely to assignment of the space group as Pnna (No. 52); since refinement proceeded well, it was adopted. In the later stages of refinement the extinction coefficient was predicted to be positive but trivially small, and was not included in the model. The maximum peak in the final difference map occurs ~1.0 Å from O4 (but not in a suitable orientation to be a potential H atom), the maximum negative peak \sim 1.5 Å from O2.

Geometry. Table of Least-Squares Planes ——————————

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. C1 (1) −0.0092 0.0011 C2 (1) 0.0105 0.0011 C3 (1) −0.0036 0.0012 C4 (1) −0.0084 0.0012 C5 (1) 0.0106 0.0012 C6 (1) −0.0006 0.0012

Mean deviation from plane is 0.0071 angstroms Chi-squared: 258.6

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. O1 (1) 0.0000 O2 (1) 0.0000 C7 (1) 0.0000

Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0

Dihedral angles between least-squares planes plane plane angle 2 1 155.74

————– Plane number 3 —————

Atoms Defining Plane Distance e.s.d. C10 (1) 0.0542 0.0011 C11 (1) −0.0007 0.0012 C12 (1) −0.0542 0.0013 C13 (1) −0.0171 0.0012 C14 (1) 0.0339 0.0012 C15 (1) 0.0292 0.0013 C16 (1) −0.0415 0.0012 C17 (1) −0.0414 0.0011 C18 (1) 0.0149 0.0011 C19 (1) 0.0129 0.0011

Mean deviation from plane is 0.0300 angstroms Chi-squared: 9288.9

Dihedral angles between least-squares planes plane plane angle 3 1 94.71 3 2 69.17

————– Plane number 4 —————

Atoms Defining Plane Distance e.s.d. C20 (1) 0.0085 0.0011 C21 (1) 0.0010 0.0011 C22 (1) −0.0093 0.0012 C23 (1) 0.0069 0.0012 C24 (1) 0.0042 0.0012 C25 (1) −0.0121 0.0012

Mean deviation from plane is 0.0070 angstroms Chi-squared: 267.8

Dihedral angles between least-squares planes plane plane angle 4 1 26.49 4 2 139.59 4 3 106.96

————– Plane number 5 —————

Atoms Defining Plane Distance e.s.d. C26 (1) 0.0000 O3 (1) 0.0000 O4 (1) 0.0000

Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0

Dihedral angles between least-squares planes plane plane angle 5 1 45.69 5 2 112.92 5 3 85.80 5 4 29.55

————– Plane number 6 —————

Atoms Defining Plane Distance e.s.d. C29 (1) 0.0203 0.0010 C30 (1) −0.0051 0.0011 C31 (1) −0.0130 0.0012 C32 (1) −0.0097 0.0012 C33 (1) 0.0140 0.0012 C34 (1) 0.0071 0.0012 C35 (1) −0.0171 0.0012 C36 (1) −0.0136 0.0011 C37 (1) 0.0047 0.0010 C38 (1) 0.0022 0.0010

Mean deviation from plane is 0.0107 angstroms Chi-squared: 1221.2

Dihedral angles between least-squares planes plane plane angle 6 1 112.14 6 2 51.55 6 3 88.00 6 4 88.75 6 5 67.11

————– Plane number 7 —————

Atoms Defining Plane Distance e.s.d. C39 (1) −0.0080 0.0012 C40 (1) −0.0018 0.0011 C41 (1) 0.0092 0.0011 C42 (1) −0.0062 0.0011 C43 (1) −0.0044 0.0012 C44 (1) 0.0132 0.0013

Mean deviation from plane is 0.0071 angstroms Chi-squared: 251.6

Dihedral angles between least-squares planes plane plane angle 7 1 19.77 7 2 147.97 7 3 107.76 7 4 8.43 7 5 36.60 7 6 97.16

————– Plane number 8 —————

Atoms Defining Plane Distance e.s.d. C45 (1) 0.0000 O5 (1) 0.0000 O6 (1) 0.0000

Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0

Dihedral angles between least-squares planes plane plane angle 8 1 41.17 8 2 116.10 8 3 81.34 8 4 29.64 8 5 7.29 8 6 72.89 8 7 35.42

————– Plane number 9 —————

Atoms Defining Plane Distance e.s.d. C48 (1) −0.0121 0.0010 C49 (1) 0.0056 0.0011 C50 (1) 0.0148 0.0012 C51 (1) 0.0002 0.0013 C52 (1) −0.0055 0.0012 C53 (1) −0.0029 0.0013 C54 (1) 0.0112 0.0012 C55 (1) 0.0097 0.0011 C56 (1) −0.0083 0.0011 C57 (1) −0.0056 0.0011

Mean deviation from plane is 0.0076 angstroms Chi-squared: 600.7

Dihedral angles between least-squares planes plane plane angle 9 1 106.65 9 2 58.19 9 3 92.69 9 4 82.51 9 5 62.43 9 6 6.92 9 7 90.87 9 8 68.62

Refinement. At an intermediate stage of refinement, three low-angle reflections (040, 111 and 212) with δ/σ values considerably larger than for any other reflections, were excluded from further refinement.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.65905 (5)	0.24136 (3)	0.34322 (6)	0.0656 (4)
O2	0.52933 (5)	0.23514 (2)	0.33470 (6)	0.0473 (3)
O3	0.33206 (5)	0.55083 (3)	0.66746 (7)	0.0488 (3)
O4	0.25596 (5)	0.59842 (2)	0.64541 (6)	0.0476 (3)
O5	0.25809 (5)	0.62162 (3)	0.82598 (7)	0.0516 (3)
O6	0.33439 (5)	0.57388 (2)	0.84716 (6)	0.0432 (3)
C1	0.59125 (7)	0.22586 (3)	0.48705 (9)	0.0299 (4)
C2	0.52432 (7)	0.23115 (3)	0.54617 (9)	0.0281 (4)
C3	0.53084 (7)	0.22138 (3)	0.64277 (9)	0.0335 (4)
C4	0.60003 (8)	0.20769 (3)	0.68136 (9)	0.0392 (4)
C5	0.66591 (7)	0.20362 (3)	0.62286 (10)	0.0395 (4)
C6	0.66149 (7)	0.21231 (3)	0.52663 (10)	0.0374 (4)
C7	0.59279 (7)	0.23481 (3)	0.38279 (9)	0.0350 (4)
C8	0.44564 (7)	0.24731 (3)	0.51219 (9)	0.0300 (4)
C9	0.38460 (9)	0.21722 (4)	0.50015 (13)	0.0428 (5)
C10	0.42012 (7)	0.27734 (3)	0.57976 (8)	0.0295 (4)
C11	0.35453 (7)	0.27506 (4)	0.63766 (9)	0.0395 (4)
C12	0.33351 (8)	0.30299 (4)	0.70202 (10)	0.0464 (5)
C13	0.37998 (8)	0.33250 (4)	0.70909 (9)	0.0453 (5)
C14	0.49580 (9)	0.36757 (4)	0.65575 (9)	0.0442 (5)
C15	0.55948 (8)	0.37188 (4)	0.59706 (10)	0.0468 (5)
C16	0.57680 (7)	0.34607 (4)	0.52707 (10)	0.0393 (4)
C17	0.53210 (7)	0.31568 (3)	0.52058 (9)	0.0314 (4)
C18	0.46699 (7)	0.30942 (3)	0.58281 (8)	0.0286 (4)
C19	0.44736 (7)	0.33681 (4)	0.65026 (9)	0.0347 (4)
C20	0.28444 (7)	0.56082 (3)	0.50974 (8)	0.0268 (4)
C21	0.21975 (7)	0.56903 (3)	0.44954 (8)	0.0255 (4)
C22	0.22503 (7)	0.55861 (3)	0.35359 (8)	0.0318 (4)
C23	0.29113 (8)	0.54131 (3)	0.31688 (9)	0.0354 (4)
C24	0.35416 (7)	0.53310 (3)	0.37661 (9)	0.0350 (4)
C25	0.35000 (7)	0.54248 (3)	0.47273 (9)	0.0331 (4)
C26	0.28821 (7)	0.57168 (4)	0.61280 (9)	0.0303 (4)
C27	0.14141 (7)	0.58482 (3)	0.48680 (9)	0.0274 (4)
C28	0.08931 (9)	0.55373 (4)	0.52112 (11)	0.0363 (5)
C29	0.10165 (7)	0.60894 (3)	0.41214 (8)	0.0267 (4)
C30	0.03386 (7)	0.59899 (3)	0.36444 (9)	0.0331 (4)
C31	−0.00181 (7)	0.62103 (4)	0.29413 (9)	0.0373 (4)
C32	0.03000 (7)	0.65338 (4)	0.27208 (9)	0.0343 (4)
C33	0.13415 (8)	0.69900 (3)	0.29728 (8)	0.0344 (4)
C34	0.20022 (7)	0.71051 (3)	0.34405 (9)	0.0381 (4)
C35	0.23537 (7)	0.68930 (4)	0.41579 (9)	0.0368 (4)
C36	0.20426 (7)	0.65654 (3)	0.43850 (8)	0.0309 (4)
C37	0.13577 (7)	0.64329 (3)	0.39103 (8)	0.0251 (4)
C38	0.09964 (7)	0.66538 (3)	0.31962 (8)	0.0280 (4)
C39	0.29434 (7)	0.60750 (3)	0.98608 (8)	0.0272 (4)
C40	0.35789 (7)	0.60071 (3)	1.04936 (8)	0.0247 (4)
C41	0.34601 (7)	0.60770 (3)	1.14677 (8)	0.0293 (4)
C42	0.27428 (7)	0.62036 (3)	1.18174 (8)	0.0324 (4)
C43	0.21242 (7)	0.62715 (3)	1.11899 (9)	0.0348 (4)
C44	0.22309 (7)	0.62116 (3)	1.02166 (9)	0.0346 (4)
C45	0.29849 (7)	0.59938 (4)	0.88138 (9)	0.0314 (4)
C46	0.44084 (7)	0.59059 (3)	1.01340 (9)	0.0270 (4)
C47	0.48486 (8)	0.62547 (4)	0.99057 (11)	0.0386 (5)
C48	0.48455 (6)	0.56602 (3)	1.08276 (8)	0.0266 (4)
C49	0.55173 (7)	0.57673 (3)	1.13069 (8)	0.0332 (4)
C50	0.59298 (7)	0.55381 (4)	1.19378 (9)	0.0432 (5)
C51	0.56687 (8)	0.52018 (4)	1.20933 (9)	0.0453 (5)
C52	0.47076 (9)	0.47205 (4)	1.17614 (10)	0.0500 (5)
C53	0.40560 (10)	0.45970 (4)	1.12999 (11)	0.0537 (5)
C54	0.36380 (8)	0.48187 (4)	1.06503 (10)	0.0475 (5)
C55	0.38868 (7)	0.51633 (3)	1.04893 (9)	0.0362 (4)
C56	0.45634 (7)	0.53024 (3)	1.09708 (8)	0.0286 (4)
C57	0.49851 (7)	0.50734 (4)	1.16161 (9)	0.0354 (4)
H1O3	0.3311 (9)	0.5608 (4)	0.7339 (12)	0.111 (6)*
H1O5	0.2603 (10)	0.6120 (5)	0.7532 (13)	0.132 (7)*
H1O1	0.6572	0.2493	0.2570	0.156*	0.500
H1O2	0.5288	0.2489	0.2565	0.113*	0.500
H3	0.4846	0.2243	0.6850	0.040*
H4	0.6024	0.2009	0.7497	0.047*
H5	0.7157	0.1945	0.6500	0.047*
H6	0.7081	0.2090	0.4852	0.045*
H8	0.4523 (5)	0.2582 (3)	0.4476 (7)	0.022 (3)*
H9B	0.3308 (7)	0.2264 (3)	0.4746 (8)	0.044 (4)*
H9C	0.4046 (7)	0.1990 (3)	0.4521 (9)	0.054 (4)*
H9A	0.3739 (7)	0.2041 (3)	0.5624 (9)	0.047 (4)*
H11	0.3212	0.2536	0.6346	0.047*
H12	0.2854	0.3010	0.7414	0.056*
H13	0.3664	0.3511	0.7560	0.054*
H14	0.4831	0.3862	0.7031	0.053*
H15	0.5933	0.3931	0.6037	0.056*
H16	0.6212	0.3498	0.4825	0.047*
H17	0.5455	0.2978	0.4716	0.038*
H22	0.1804	0.5637	0.3103	0.038*
H23	0.2932	0.5349	0.2483	0.042*
H24	0.4011	0.5208	0.3511	0.042*
H25	0.3939	0.5362	0.5160	0.040*
H27	0.1534 (5)	0.6001 (3)	0.5430 (7)	0.020 (3)*
H28B	0.1180 (6)	0.5401 (3)	0.5746 (8)	0.042 (4)*
H28C	0.0767 (6)	0.5364 (3)	0.4660 (8)	0.039 (4)*
H28A	0.0368 (7)	0.5625 (3)	0.5493 (8)	0.045 (4)*
H30	0.0095	0.5759	0.3797	0.040*
H31	−0.0500	0.6129	0.2609	0.045*
H32	0.0047	0.6685	0.2231	0.041*
H33	0.1100	0.7141	0.2474	0.041*
H34	0.2234	0.7338	0.3276	0.046*
H35	0.2826	0.6980	0.4499	0.044*
H36	0.2298	0.6420	0.4885	0.037*
H41	0.3897	0.6036	1.1922	0.035*
H42	0.2675	0.6245	1.2511	0.039*
H43	0.1615	0.6361	1.1434	0.042*
H44	0.1799	0.6266	0.9766	0.041*
H46	0.4348 (5)	0.5770 (3)	0.9531 (7)	0.019 (3)*
H47C	0.4906 (6)	0.6422 (3)	1.0521 (9)	0.054 (4)*
H47A	0.4529 (6)	0.6396 (3)	0.9415 (8)	0.046 (4)*
H47B	0.5395 (7)	0.6206 (3)	0.9632 (8)	0.046 (4)*
H49	0.5716	0.6011	1.1207	0.040*
H50	0.6410	0.5623	1.2266	0.052*
H51	0.5956	0.5045	1.2542	0.054*
H52	0.4994	0.4562	1.2206	0.060*
H53	0.3873	0.4352	1.1417	0.064*
H54	0.3169	0.4726	1.0313	0.057*
H55	0.3593	0.5315	1.0036	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0304 (5)	0.1149 (10)	0.0516 (6)	−0.0132 (6)	0.0037 (5)	0.0107 (6)
O2	0.0304 (5)	0.0773 (8)	0.0342 (5)	−0.0056 (5)	−0.0033 (5)	−0.0091 (5)
O3	0.0653 (7)	0.0505 (7)	0.0306 (6)	0.0291 (5)	−0.0124 (5)	−0.0046 (5)
O4	0.0609 (6)	0.0510 (7)	0.0310 (5)	0.0281 (5)	−0.0119 (5)	−0.0124 (5)
O5	0.0632 (6)	0.0601 (7)	0.0316 (6)	0.0319 (5)	−0.0132 (5)	−0.0055 (5)
O6	0.0496 (6)	0.0503 (7)	0.0297 (5)	0.0209 (5)	−0.0081 (4)	−0.0098 (5)
C1	0.0244 (7)	0.0269 (8)	0.0384 (8)	−0.0025 (6)	−0.0021 (6)	−0.0042 (6)
C2	0.0259 (7)	0.0223 (8)	0.0361 (8)	−0.0015 (6)	−0.0044 (6)	−0.0048 (6)
C3	0.0318 (7)	0.0306 (8)	0.0382 (8)	0.0006 (6)	−0.0006 (7)	−0.0018 (7)
C4	0.0413 (8)	0.0335 (9)	0.0428 (8)	0.0027 (7)	−0.0087 (7)	0.0040 (7)
C5	0.0318 (8)	0.0290 (9)	0.0578 (10)	0.0033 (6)	−0.0113 (8)	0.0016 (7)
C6	0.0262 (7)	0.0335 (9)	0.0526 (10)	0.0013 (6)	−0.0008 (7)	−0.0041 (7)
C7	0.0246 (8)	0.0374 (9)	0.0431 (9)	0.0002 (7)	0.0010 (7)	−0.0097 (7)
C8	0.0254 (7)	0.0344 (9)	0.0301 (8)	−0.0019 (6)	−0.0019 (6)	0.0004 (7)
C9	0.0302 (8)	0.0476 (11)	0.0507 (11)	−0.0084 (8)	−0.0045 (8)	−0.0013 (9)
C10	0.0232 (7)	0.0380 (9)	0.0273 (7)	0.0065 (6)	−0.0031 (6)	0.0050 (7)
C11	0.0298 (7)	0.0485 (10)	0.0402 (8)	0.0051 (7)	0.0026 (7)	0.0075 (7)
C12	0.0359 (8)	0.0646 (12)	0.0387 (9)	0.0193 (8)	0.0122 (7)	0.0050 (8)
C13	0.0501 (9)	0.0501 (11)	0.0356 (8)	0.0217 (8)	0.0009 (7)	−0.0022 (8)
C14	0.0632 (10)	0.0308 (9)	0.0385 (9)	0.0135 (8)	−0.0104 (8)	−0.0064 (7)
C15	0.0563 (10)	0.0315 (9)	0.0526 (10)	−0.0003 (8)	−0.0132 (8)	0.0017 (8)
C16	0.0373 (8)	0.0329 (9)	0.0477 (9)	0.0026 (7)	−0.0040 (7)	0.0061 (7)
C17	0.0302 (7)	0.0285 (8)	0.0355 (8)	0.0052 (6)	−0.0029 (6)	0.0013 (6)
C18	0.0274 (7)	0.0308 (8)	0.0276 (7)	0.0089 (6)	−0.0055 (6)	0.0018 (6)
C19	0.0386 (8)	0.0371 (9)	0.0284 (8)	0.0128 (7)	−0.0045 (7)	0.0005 (7)
C20	0.0331 (7)	0.0223 (8)	0.0251 (7)	0.0020 (6)	0.0018 (6)	−0.0001 (6)
C21	0.0326 (7)	0.0192 (7)	0.0246 (7)	−0.0011 (6)	0.0023 (6)	0.0021 (6)
C22	0.0404 (8)	0.0285 (8)	0.0263 (7)	0.0029 (6)	−0.0006 (6)	0.0013 (6)
C23	0.0525 (9)	0.0268 (8)	0.0268 (8)	−0.0001 (7)	0.0087 (7)	−0.0020 (6)
C24	0.0396 (8)	0.0292 (8)	0.0362 (8)	0.0064 (7)	0.0096 (7)	−0.0002 (7)
C25	0.0353 (8)	0.0293 (8)	0.0348 (8)	0.0043 (7)	0.0014 (6)	0.0007 (6)
C26	0.0300 (7)	0.0297 (9)	0.0311 (8)	0.0048 (7)	−0.0025 (6)	0.0002 (7)
C27	0.0328 (7)	0.0266 (8)	0.0226 (7)	0.0019 (7)	−0.0008 (6)	−0.0010 (6)
C28	0.0390 (9)	0.0360 (10)	0.0339 (9)	0.0014 (8)	0.0042 (8)	0.0045 (8)
C29	0.0291 (7)	0.0294 (8)	0.0217 (7)	0.0050 (6)	0.0010 (6)	−0.0029 (6)
C30	0.0371 (8)	0.0301 (8)	0.0321 (8)	−0.0017 (7)	−0.0018 (6)	−0.0021 (6)
C31	0.0351 (8)	0.0427 (10)	0.0341 (8)	0.0017 (7)	−0.0109 (6)	−0.0029 (7)
C32	0.0383 (8)	0.0373 (9)	0.0272 (8)	0.0100 (7)	−0.0047 (6)	0.0000 (7)
C33	0.0412 (8)	0.0329 (9)	0.0290 (8)	0.0077 (7)	0.0028 (7)	0.0046 (6)
C34	0.0439 (8)	0.0291 (9)	0.0412 (9)	−0.0001 (7)	0.0041 (7)	0.0042 (7)
C35	0.0337 (8)	0.0346 (9)	0.0421 (9)	0.0002 (7)	−0.0031 (7)	−0.0011 (7)
C36	0.0319 (7)	0.0301 (9)	0.0306 (8)	0.0055 (7)	−0.0013 (6)	−0.0008 (7)
C37	0.0253 (7)	0.0273 (8)	0.0227 (7)	0.0050 (6)	0.0019 (6)	−0.0033 (6)
C38	0.0314 (7)	0.0313 (8)	0.0212 (7)	0.0080 (7)	0.0028 (6)	−0.0030 (6)
C39	0.0274 (7)	0.0294 (8)	0.0248 (7)	0.0003 (6)	0.0015 (6)	−0.0016 (6)
C40	0.0278 (7)	0.0217 (7)	0.0247 (7)	−0.0002 (6)	0.0026 (6)	0.0008 (6)
C41	0.0326 (7)	0.0291 (8)	0.0262 (7)	0.0013 (6)	−0.0003 (6)	0.0013 (6)
C42	0.0417 (8)	0.0300 (8)	0.0256 (7)	−0.0026 (7)	0.0082 (7)	0.0002 (6)
C43	0.0291 (7)	0.0363 (9)	0.0390 (8)	0.0005 (6)	0.0082 (7)	−0.0058 (7)
C44	0.0258 (7)	0.0415 (9)	0.0364 (8)	0.0015 (6)	−0.0024 (6)	−0.0042 (7)
C45	0.0247 (7)	0.0388 (9)	0.0306 (8)	0.0050 (7)	−0.0037 (6)	−0.0013 (7)
C46	0.0284 (7)	0.0297 (8)	0.0229 (7)	0.0019 (6)	−0.0012 (6)	−0.0002 (7)
C47	0.0316 (9)	0.0417 (10)	0.0423 (10)	0.0031 (8)	0.0061 (8)	0.0124 (8)
C48	0.0273 (7)	0.0309 (8)	0.0216 (7)	0.0056 (6)	0.0028 (6)	−0.0008 (6)
C49	0.0342 (7)	0.0359 (9)	0.0296 (7)	0.0042 (7)	−0.0027 (6)	−0.0016 (7)
C50	0.0403 (8)	0.0517 (11)	0.0376 (9)	0.0107 (8)	−0.0115 (7)	−0.0047 (8)
C51	0.0570 (10)	0.0496 (11)	0.0294 (8)	0.0242 (8)	−0.0069 (7)	0.0014 (8)
C52	0.0772 (11)	0.0368 (10)	0.0361 (9)	0.0143 (9)	0.0185 (8)	0.0045 (8)
C53	0.0800 (12)	0.0283 (10)	0.0528 (10)	−0.0022 (9)	0.0306 (9)	0.0002 (8)
C54	0.0487 (9)	0.0395 (10)	0.0545 (10)	−0.0065 (8)	0.0163 (8)	−0.0110 (8)
C55	0.0370 (8)	0.0323 (9)	0.0392 (8)	0.0003 (7)	0.0087 (7)	−0.0056 (7)
C56	0.0347 (8)	0.0275 (8)	0.0236 (7)	0.0054 (7)	0.0077 (6)	−0.0022 (6)
C57	0.0498 (9)	0.0294 (9)	0.0270 (8)	0.0113 (7)	0.0104 (7)	0.0013 (7)

Geometric parameters (Å, º)

O1—C7	1.2672 (13)	C27—C29	1.5261 (15)
O1—H1O1	1.23	C27—H27	0.985 (9)
O2—C7	1.2596 (13)	C28—H28B	1.020 (11)
O2—H1O2	1.20	C28—H28C	1.024 (11)
O3—C26	1.3135 (13)	C28—H28A	1.021 (11)
O3—H1O3	0.994 (17)	C29—C30	1.3706 (15)
O4—C26	1.2239 (13)	C29—C37	1.4367 (15)
O5—C45	1.3200 (13)	C30—C31	1.4095 (16)
O5—H1O5	1.070 (18)	C30—H30	0.98
O6—C45	1.2240 (13)	C31—C32	1.3573 (16)
C1—C2	1.4073 (15)	C31—H31	0.98
C1—C6	1.3988 (15)	C32—C38	1.4179 (15)
C1—C7	1.4817 (16)	C32—H32	0.98
C2—C3	1.3905 (16)	C33—C34	1.3577 (16)
C2—C8	1.5305 (15)	C33—C38	1.4186 (16)
C3—C4	1.3804 (15)	C33—H33	0.98
C3—H3	0.98	C34—C35	1.4020 (16)
C4—C5	1.3823 (16)	C34—H34	0.98
C4—H4	0.98	C35—C36	1.3685 (15)
C5—C6	1.3731 (17)	C35—H35	0.98
C5—H5	0.98	C36—C37	1.4172 (15)
C6—H6	0.98	C36—H36	0.98
C8—C9	1.5329 (17)	C37—C38	1.4244 (15)
C8—C10	1.5231 (16)	C39—C40	1.4064 (15)
C8—H8	0.988 (9)	C39—C44	1.3942 (15)
C9—H9B	1.033 (12)	C39—C45	1.4823 (16)
C9—H9C	1.010 (12)	C40—C41	1.3879 (14)
C9—H9A	1.009 (11)	C40—C46	1.5309 (15)
C10—C11	1.3676 (15)	C41—C42	1.3851 (15)
C10—C18	1.4364 (15)	C41—H41	0.98
C11—C12	1.4172 (17)	C42—C43	1.3802 (16)
C11—H11	0.98	C42—H42	0.98
C12—C13	1.3561 (17)	C43—C44	1.3775 (16)
C12—H12	0.98	C43—H43	0.98
C13—C19	1.4062 (16)	C44—H44	0.98
C13—H13	0.98	C46—C47	1.5330 (17)
C14—C15	1.3554 (17)	C46—C48	1.5190 (15)
C14—C19	1.4119 (17)	C46—H46	0.982 (9)
C14—H14	0.98	C47—H47C	1.062 (12)
C15—C16	1.3980 (17)	C47—H47A	1.016 (12)
C15—H15	0.98	C47—H47B	1.011 (11)
C16—C17	1.3656 (16)	C48—C49	1.3717 (15)
C16—H16	0.98	C48—C56	1.4328 (15)
C17—C18	1.4141 (15)	C49—C50	1.4070 (16)
C17—H17	0.98	C49—H49	0.98
C18—C19	1.4244 (16)	C50—C51	1.3488 (17)
C20—C21	1.4057 (15)	C50—H50	0.98
C20—C25	1.3971 (15)	C51—C57	1.4117 (17)
C20—C26	1.4845 (15)	C51—H51	0.98
C21—C22	1.3868 (15)	C52—C53	1.3512 (18)
C21—C27	1.5349 (15)	C52—C57	1.4139 (18)
C22—C23	1.3845 (15)	C52—H52	0.98
C22—H22	0.98	C53—C54	1.4111 (18)
C23—C24	1.3802 (16)	C53—H53	0.98
C23—H23	0.98	C54—C55	1.3724 (16)
C24—C25	1.3777 (15)	C54—H54	0.98
C24—H24	0.98	C55—C56	1.4191 (15)
C25—H25	0.98	C55—H55	0.98
C27—C28	1.5319 (17)	C56—C57	1.4267 (16)
C7—O1—H1O1	116.3	H28B—C28—H28C	108.8 (9)
C7—O2—H1O2	119.2	H28B—C28—H28A	107.1 (9)
C26—O3—H1O3	107.6 (9)	H28C—C28—H28A	108.0 (9)
C45—O5—H1O5	108.4 (9)	C27—C29—C30	122.12 (11)
C2—C1—C6	120.07 (11)	C27—C29—C37	119.34 (10)
C2—C1—C7	123.28 (11)	C30—C29—C37	118.54 (11)
C6—C1—C7	116.64 (11)	C29—C30—C31	121.97 (11)
C1—C2—C3	117.32 (11)	C29—C30—H30	119.0
C1—C2—C8	124.80 (11)	C31—C30—H30	119.0
C3—C2—C8	117.88 (11)	C30—C31—C32	120.49 (11)
C2—C3—C4	122.42 (11)	C30—C31—H31	119.7
C2—C3—H3	118.8	C32—C31—H31	119.8
C4—C3—H3	118.8	C31—C32—C38	120.28 (11)
C3—C4—C5	119.48 (12)	C31—C32—H32	119.9
C3—C4—H4	120.3	C38—C32—H32	119.8
C5—C4—H4	120.3	C34—C33—C38	120.85 (11)
C4—C5—C6	119.90 (11)	C34—C33—H33	119.6
C4—C5—H5	120.0	C38—C33—H33	119.6
C6—C5—H5	120.1	C33—C34—C35	120.31 (12)
C1—C6—C5	120.77 (11)	C33—C34—H34	119.8
C1—C6—H6	119.6	C35—C34—H34	119.9
C5—C6—H6	119.6	C34—C35—C36	120.47 (11)
O1—C7—O2	121.16 (12)	C34—C35—H35	119.8
O1—C7—C1	118.69 (11)	C36—C35—H35	119.8
O2—C7—C1	120.14 (11)	C35—C36—C37	121.19 (11)
C2—C8—C9	108.96 (11)	C35—C36—H36	119.4
C2—C8—C10	110.28 (10)	C37—C36—H36	119.4
C2—C8—H8	110.0 (6)	C29—C37—C36	122.93 (11)
C9—C8—C10	114.71 (11)	C29—C37—C38	119.22 (11)
C9—C8—H8	106.2 (6)	C36—C37—C38	117.85 (11)
C10—C8—H8	106.6 (6)	C32—C38—C33	121.21 (11)
C8—C9—H9B	112.4 (6)	C32—C38—C37	119.48 (11)
C8—C9—H9C	110.1 (7)	C33—C38—C37	119.31 (11)
C8—C9—H9A	112.6 (7)	C40—C39—C44	120.10 (11)
H9B—C9—H9C	106.9 (9)	C40—C39—C45	122.41 (10)
H9B—C9—H9A	107.4 (9)	C44—C39—C45	117.45 (10)
H9C—C9—H9A	107.1 (9)	C39—C40—C41	117.47 (10)
C8—C10—C11	122.82 (12)	C39—C40—C46	122.48 (10)
C8—C10—C18	118.56 (10)	C41—C40—C46	119.60 (10)
C11—C10—C18	118.62 (12)	C40—C41—C42	121.99 (11)
C10—C11—C12	121.62 (12)	C40—C41—H41	119.0
C10—C11—H11	119.2	C42—C41—H41	119.0
C12—C11—H11	119.2	C41—C42—C43	120.10 (11)
C11—C12—C13	120.01 (12)	C41—C42—H42	119.9
C11—C12—H12	120.0	C43—C42—H42	120.0
C13—C12—H12	120.0	C42—C43—C44	119.15 (11)
C12—C13—C19	121.16 (12)	C42—C43—H43	120.4
C12—C13—H13	119.4	C44—C43—H43	120.4
C19—C13—H13	119.4	C39—C44—C43	121.15 (11)
C15—C14—C19	121.47 (12)	C39—C44—H44	119.4
C15—C14—H14	119.3	C43—C44—H44	119.4
C19—C14—H14	119.3	O5—C45—O6	121.35 (11)
C14—C15—C16	119.90 (13)	O5—C45—C39	114.50 (11)
C14—C15—H15	120.0	O6—C45—C39	124.13 (12)
C16—C15—H15	120.1	C40—C46—C47	107.37 (10)
C15—C16—C17	120.29 (12)	C40—C46—C48	112.73 (9)
C15—C16—H16	119.8	C40—C46—H46	108.0 (5)
C17—C16—H16	119.9	C47—C46—C48	114.20 (10)
C16—C17—C18	121.68 (12)	C47—C46—H46	108.4 (6)
C16—C17—H17	119.1	C48—C46—H46	105.9 (6)
C18—C17—H17	119.2	C46—C47—H47C	112.4 (6)
C10—C18—C17	123.13 (11)	C46—C47—H47A	108.9 (6)
C10—C18—C19	119.44 (11)	C46—C47—H47B	111.3 (7)
C17—C18—C19	117.42 (12)	H47C—C47—H47A	106.1 (9)
C13—C19—C14	121.92 (13)	H47C—C47—H47B	108.9 (9)
C13—C19—C18	118.99 (12)	H47A—C47—H47B	109.0 (9)
C14—C19—C18	119.10 (12)	C46—C48—C49	121.95 (11)
C21—C20—C25	120.17 (11)	C46—C48—C56	119.39 (10)
C21—C20—C26	122.89 (11)	C49—C48—C56	118.64 (11)
C25—C20—C26	116.92 (11)	C48—C49—C50	122.00 (12)
C20—C21—C22	117.17 (11)	C48—C49—H49	119.0
C20—C21—C27	123.46 (10)	C50—C49—H49	119.0
C22—C21—C27	119.00 (11)	C49—C50—C51	120.35 (12)
C21—C22—C23	122.29 (11)	C49—C50—H50	119.8
C21—C22—H22	118.9	C51—C50—H50	119.8
C23—C22—H22	118.8	C50—C51—C57	120.55 (12)
C22—C23—C24	120.19 (11)	C50—C51—H51	119.7
C22—C23—H23	119.9	C57—C51—H51	119.7
C24—C23—H23	119.9	C53—C52—C57	121.33 (13)
C23—C24—C25	118.87 (11)	C53—C52—H52	119.3
C23—C24—H24	120.6	C57—C52—H52	119.3
C25—C24—H24	120.6	C52—C53—C54	120.40 (13)
C20—C25—C24	121.28 (11)	C52—C53—H53	119.8
C20—C25—H25	119.4	C54—C53—H53	119.8
C24—C25—H25	119.4	C53—C54—C55	120.14 (13)
O3—C26—O4	121.44 (11)	C53—C54—H54	119.9
O3—C26—C20	114.54 (11)	C55—C54—H54	119.9
O4—C26—C20	123.97 (11)	C54—C55—C56	120.85 (12)
C21—C27—C28	107.77 (10)	C54—C55—H55	119.6
C21—C27—C29	112.15 (9)	C56—C55—H55	119.6
C21—C27—H27	108.2 (6)	C48—C56—C55	122.92 (11)
C28—C27—C29	113.99 (10)	C48—C56—C57	118.77 (11)
C28—C27—H27	108.1 (6)	C55—C56—C57	118.31 (12)
C29—C27—H27	106.4 (6)	C51—C57—C52	121.37 (13)
C27—C28—H28B	109.4 (6)	C51—C57—C56	119.68 (12)
C27—C28—H28C	111.6 (6)	C52—C57—C56	118.95 (12)
C27—C28—H28A	111.8 (6)
O1—C7—C1—C2	155.37 (12)	C24—C25—C20—C26	−176.20 (11)
O1—C7—C1—C6	−23.11 (17)	C25—C20—C21—C27	172.09 (11)
O2—C7—C1—C2	−26.01 (18)	C26—C20—C21—C27	−9.65 (17)
O2—C7—C1—C6	155.51 (11)	C27—C29—C30—C31	−178.70 (11)
O3—C26—C20—C21	153.13 (11)	C27—C29—C37—C36	−1.76 (16)
O3—C26—C20—C25	−28.56 (15)	C27—C29—C37—C38	178.49 (10)
O4—C26—C20—C21	−29.31 (18)	C28—C27—C29—C30	−14.23 (16)
O4—C26—C20—C25	148.99 (12)	C28—C27—C29—C37	165.49 (11)
O5—C45—C39—C40	−147.21 (11)	C29—C30—C31—C32	−0.70 (19)
O5—C45—C39—C44	35.12 (16)	C29—C37—C36—C35	179.46 (11)
O6—C45—C39—C40	34.42 (18)	C29—C37—C38—C32	1.15 (16)
O6—C45—C39—C44	−143.25 (12)	C29—C37—C38—C33	−178.73 (10)
C1—C2—C3—C4	1.33 (18)	C30—C29—C37—C36	177.97 (11)
C1—C2—C8—C9	103.84 (14)	C30—C29—C37—C38	−1.78 (16)
C1—C2—C8—C10	−129.42 (12)	C30—C31—C32—C38	0.01 (19)
C1—C6—C5—C4	1.0 (2)	C31—C30—C29—C37	1.57 (17)
C2—C1—C6—C5	0.79 (19)	C31—C32—C38—C33	179.62 (11)
C2—C3—C4—C5	0.46 (19)	C31—C32—C38—C37	−0.27 (17)
C2—C8—C10—C11	−112.94 (12)	C32—C38—C33—C34	179.10 (11)
C2—C8—C10—C18	67.03 (14)	C32—C38—C37—C36	−178.62 (10)
C3—C2—C1—C6	−1.93 (17)	C33—C34—C35—C36	0.99 (19)
C3—C2—C1—C7	179.64 (11)	C33—C38—C37—C36	1.50 (16)
C3—C2—C8—C9	−77.08 (14)	C34—C33—C38—C37	−1.02 (17)
C3—C2—C8—C10	49.66 (14)	C34—C35—C36—C37	−0.45 (18)
C3—C4—C5—C6	−1.7 (2)	C35—C34—C33—C38	−0.24 (18)
C4—C3—C2—C8	−177.82 (11)	C35—C36—C37—C38	−0.78 (17)
C5—C6—C1—C7	179.33 (12)	C39—C40—C41—C42	0.99 (17)
C6—C1—C2—C8	177.15 (11)	C39—C40—C46—C47	84.72 (14)
C7—C1—C2—C8	−1.28 (18)	C39—C40—C46—C48	−148.64 (11)
C8—C10—C11—C12	178.05 (11)	C39—C44—C43—C42	1.78 (19)
C8—C10—C18—C17	5.21 (16)	C40—C39—C44—C43	−2.18 (19)
C8—C10—C18—C19	−175.70 (10)	C40—C41—C42—C43	−1.40 (18)
C9—C8—C10—C11	10.52 (17)	C40—C46—C48—C49	−114.08 (12)
C9—C8—C10—C18	−169.51 (11)	C40—C46—C48—C56	67.55 (14)
C10—C11—C12—C13	−1.70 (19)	C41—C40—C39—C44	0.77 (17)
C10—C18—C17—C16	−178.22 (11)	C41—C40—C39—C45	−176.84 (11)
C10—C18—C19—C13	−3.11 (16)	C41—C40—C46—C47	−87.40 (13)
C10—C18—C19—C14	177.22 (11)	C41—C40—C46—C48	39.24 (15)
C11—C10—C18—C17	−174.82 (11)	C41—C42—C43—C44	−0.01 (18)
C11—C10—C18—C19	4.27 (16)	C42—C41—C40—C46	173.51 (11)
C11—C12—C13—C19	2.9 (2)	C43—C44—C39—C45	175.55 (12)
C12—C11—C10—C18	−1.92 (18)	C44—C39—C40—C46	−171.51 (11)
C12—C13—C19—C14	179.15 (12)	C45—C39—C40—C46	10.88 (18)
C12—C13—C19—C18	−0.51 (18)	C46—C48—C49—C50	−178.97 (11)
C13—C19—C14—C15	−178.33 (12)	C46—C48—C56—C55	0.12 (16)
C13—C19—C18—C17	176.03 (10)	C46—C48—C56—C57	179.30 (10)
C14—C15—C16—C17	−3.15 (19)	C47—C46—C48—C49	8.82 (16)
C14—C19—C18—C17	−3.63 (16)	C47—C46—C48—C56	−169.55 (11)
C15—C14—C19—C18	1.32 (19)	C48—C49—C50—C51	−0.30 (19)
C15—C16—C17—C18	0.69 (18)	C48—C56—C55—C54	−179.93 (11)
C16—C15—C14—C19	2.1 (2)	C48—C56—C57—C51	−0.32 (17)
C16—C17—C18—C19	2.67 (17)	C48—C56—C57—C52	179.83 (10)
C20—C21—C22—C23	−0.93 (18)	C49—C48—C56—C55	−178.31 (10)
C20—C21—C27—C28	−84.68 (14)	C49—C48—C56—C57	0.88 (16)
C20—C21—C27—C29	149.06 (11)	C49—C50—C51—C57	0.9 (2)
C20—C25—C24—C23	−1.64 (18)	C50—C49—C48—C56	−0.59 (17)
C21—C20—C25—C24	2.15 (18)	C50—C51—C57—C52	179.27 (12)
C21—C22—C23—C24	1.45 (19)	C50—C51—C57—C56	−0.57 (19)
C21—C27—C29—C30	108.58 (12)	C51—C57—C52—C53	−179.60 (12)
C21—C27—C29—C37	−71.70 (13)	C51—C57—C56—C55	178.90 (10)
C22—C21—C20—C25	−0.84 (17)	C52—C53—C54—C55	−0.6 (2)
C22—C21—C20—C26	177.42 (11)	C52—C57—C56—C55	−0.94 (16)
C22—C21—C27—C28	88.13 (13)	C53—C52—C57—C56	0.25 (19)
C22—C21—C27—C29	−38.13 (15)	C53—C54—C55—C56	−0.11 (19)
C22—C23—C24—C25	−0.13 (18)	C54—C53—C52—C57	0.5 (2)
C23—C22—C21—C27	−174.19 (11)	C54—C55—C56—C57	0.88 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O1^i	1.23	1.43	2.660 (2)	177 (2)
O2—H1O2···O2^i	1.20	1.40	2.594 (2)	179 (2)
O3—H1O3···O6	0.99 (2)	1.64 (2)	2.633 (2)	175 (2)
O5—H1O5···O4	1.07 (2)	1.58 (2)	2.646 (2)	175 (2)
C13—H13···O5^ii	0.98	2.52	3.312 (2)	137
C51—H51···O3^iii	0.98	2.64	3.585 (2)	163
C32—H32···O2^iv	0.98	2.68	3.539 (2)	147
C33—H33···O2^iv	0.98	2.72	3.570 (2)	145
C11—H11···O1^v	0.98	2.79	3.536 (2)	134
C8—H8···O2	0.98	2.21	2.869 (2)	123
C27—H27···O4	0.98	2.24	2.967 (2)	130
C46—H46···O6	0.98	2.24	2.983 (2)	131
C25—H25···O3	0.98	2.40	2.730 (2)	99
C6—H6···O1	0.98	2.45	2.762 (2)	98
C44—H44···O5	0.98	2.47	2.772 (2)	97
C55—H55···O6	0.98	2.72	3.642 (2)	158
C36—H36···O4	0.98	2.75	3.698 (2)	163

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