A 1:1:1 chloro­form/tetra­hydro­furan solvate of p-tert-butyl­tetra­homo­dioxa­calix­[4]­arene

The title compound, 7,13,21,27-tetra-tert-butyl-3,17-di­oxa­penta­cyclo­[23.3.1.1^5,9.1^11,15.1^9,23]ditriaconta-1(29),­5,­7,­9(30),11(31),­12,­14,­19(32),­20,­22,­25,­27-do­deca­ene-29,­30,­31,­32-tetraol, crystallizes as a solvate with one mol­ecule of chloro­form and one mol­ecule of tetra­hydro­furan, C₄₆H₆₀O₆·CHCl₃·C₄H₈O. The calixarene assumes a cone-like conformation stabilized by intramolecular hydrogen bonds involving both phenolic and ether O atoms. The two solvent mol­ecules are located in each of the two half-cone cavities of the calixarene.

S1. Comment

We have recently reported the first crystal structures of p-tert-butyltetrahomodioxacalix[4]arene as well as of its uranyl ion complex (Thuéry et al., 2000). Two forms presenting slightly different conformations have been found for the uncomplexed ligand, associated with some differences in the ether bridge conformations and intramolecular hydrogen-bond pattern. In each case, two solvent molecules (acetonitrile or pyridine) are included in the calixarene cavity. \sch

The main features of these structures are present in the case of the new solvate, (I), but the conformation is slightly different from the previous ones. The asymmetric unit in 1 is composed of one calixarene and two different solvent molecules. The calixarene symmetry was higher in one of the cases previously reported, in which the molecule was located around a binary axis, (II). If the plane defined by the four phenolic oxygen atoms is taken as a reference (highest deviation #from mean plane 0.324 (3) Å), the dihedral #angles made with it by the four phenyl rings are 124.5 (1), 126.4 (1), #157.5 (2) and 159.6 (1)° in 1, i.e. they span a wider range than those in the #more symmetrical and regular form 2 previously described #(132.8 (2)–141.2 (2)°). However, this from mean plane 0.459 (4) Å), the dihedral angles made with it by the four phenyl rings are 132.4 (1), 125.7 (1), 148.2 (2) and 156.2 (1)° in (I), i.e. they span a wider range than those in the more symmetrical and regular form (II) previously described [132.8 (2)–141.2 (2)°]. However, this range was even larger in the second form previously described (3) [109.4 (1)–157.3 (2)°]. The intramolecular hydrogen-bond pattern is different in the two previous forms: in 2, two phenolic units give bifurcated hydrogen bonds with the other phenolic units and the ether groups whereas in (III), one of those bifurcated bonds is replaced by a simple one (with the ether group). In (I), both hydrogen bonds are bifurcated, the phenol···phenol ones being seemingly somewhat less strong than in (II). The conformation around the ether bridges is identical to that in (II), the slight geometrical differences between those two compounds being possibly connected to the difference in the solvents included. By contrast with the parent calixarenes, in which the hydrogen-bond pattern is rather well defined and contributes to the rigidity of the molecule, the presence of the ether groups in oxacalixarenes makes this pattern more variable and the molecule more flexible.

The inclusion of two chemically different solvent molecules in a calixarene cavity is a somewhat uncommon feature, at least for small calixarenes [in both compounds (II) and (III), two identical molecules were included, acetonitrile in (II), pyridine in (III)]. It has been suggested that the ability of calixarenes to held two different species relatively close one to the other was indicative of their potential as 'enzyme mimics' (Asfari et al., 1991). The location of the choroform hydrogen atom is indicative of a possible hydrogen bond with the oxygen atom of tetrahydrofuran. Feeble interactions are thus present between the three species in this complex.

S2. Experimental

p-tert-Butyltetrahomodioxacalix[4]arene was synthesized as previously reported (Dhawan & Gutsche, 1983) and recrystallized from chloroform/tetrahydrofuran (1:1).

S3. Refinement

4517 Friedel pairs have been measured. Hydroxyl and chloroform protons were found on the Fourier-difference map and introduced as riding atoms with a displacement parameter equal to 1.2 times that of the parent atom. All other hydrogen atoms were introduced at calculated positions as riding atoms with a displacement parameter equal to 1.2 (CH, CH₂) or 1.5 (CH₃) times that of the parent atom. The tetrahydrofuran molecule bahaves badly on refinement and some restraints had to be applied to the displacement parameters. One of the C—C distances in this molecule is shorter than usual [1.425 (14) Å].

Computing details

Data collection: Kappa-CCD Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 1999) and PARST97 (Nardelli, 1995).

Figures

Fig. 1. The title molecule with atomic numbering scheme. Hydrogen atoms omitted for clarity unless those involved in hydrogen bonds, which are drawn as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability level.

(I)

Crystal data

C46H60O6·CHCl3·C4H8O	Dx = 1.213 Mg m^−3
Mr = 900.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 35687 reflections
a = 9.2248 (5) Å	θ = 2.7–25.7°
b = 17.6451 (15) Å	µ = 0.24 mm^−1
c = 30.282 (3) Å	T = 100 K
V = 4929.1 (7) Å^3	Parallelepipedic, colourless
Z = 4	0.28 × 0.28 × 0.25 mm
F(000) = 1928

Data collection

Nonius Kappa-CCD diffractometer	5464 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.084
Graphite monochromator	θmax = 25.7°, θmin = 2.7°
Detector resolution: 18 pixels mm^-1	h = 0→10
ϕ scans	k = −21→21
35687 measured reflections	l = −36→36
9064 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.078	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.213	w = 1/[σ^2(Fo^2) + (0.1216P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max = 0.001
9064 reflections	Δρmax = 0.71 e Å^−3
562 parameters	Δρmin = −0.39 e Å^−3
42 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00

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. Structure solved by direct methods and expanded by subsequent Fourier-difference synthesis. All non-hydrogen atoms have been refined anisotropically. The structure has been refined as corresponding to a racemic twin. 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
O1	0.8511 (3)	0.41297 (18)	0.05789 (11)	0.0224 (8)
H1	0.8944	0.4241	0.0344	0.027*
O2	0.9551 (3)	0.5157 (2)	−0.00001 (11)	0.0258 (8)
O3	0.7592 (4)	0.4037 (2)	−0.03249 (12)	0.0350 (9)
H3	0.7070	0.3578	−0.0342	0.042*
O4	0.5418 (3)	0.30084 (19)	−0.03874 (11)	0.0233 (8)
H4	0.4826	0.2992	−0.0093	0.028*
O5	0.3058 (3)	0.30112 (19)	0.01185 (11)	0.0242 (8)
O6	0.5522 (3)	0.38272 (19)	0.04573 (10)	0.0213 (7)
H6	0.6490	0.3939	0.0506	0.026*
C1	0.8370 (4)	0.4743 (3)	0.08699 (16)	0.0195 (10)
C2	0.7533 (4)	0.4645 (3)	0.12435 (15)	0.0179 (10)
C3	0.7346 (5)	0.5263 (3)	0.15212 (16)	0.0217 (10)
H3A	0.6772	0.5202	0.1771	0.026*
C4	0.7976 (5)	0.5974 (3)	0.14454 (16)	0.0228 (11)
C5	0.8830 (5)	0.6040 (3)	0.10650 (16)	0.0214 (10)
H5	0.9257	0.6505	0.1001	0.026*
C6	0.9060 (4)	0.5433 (3)	0.07784 (16)	0.0197 (10)
C7	0.7738 (6)	0.6632 (3)	0.17627 (19)	0.0316 (12)
C8	0.8539 (10)	0.6492 (4)	0.2188 (3)	0.067 (2)
H8A	0.8330	0.5990	0.2292	0.100*
H8B	0.8236	0.6856	0.2405	0.100*
H8C	0.9562	0.6542	0.2138	0.100*
C9	0.6100 (7)	0.6699 (4)	0.1870 (3)	0.058 (2)
H9A	0.5570	0.6793	0.1602	0.086*
H9B	0.5948	0.7110	0.2072	0.086*
H9C	0.5767	0.6235	0.2000	0.086*
C10	0.8140 (9)	0.7389 (3)	0.1562 (2)	0.0534 (19)
H10A	0.9170	0.7411	0.1518	0.080*
H10B	0.7847	0.7790	0.1757	0.080*
H10C	0.7659	0.7447	0.1283	0.080*
C11	1.0082 (5)	0.5516 (3)	0.03893 (15)	0.0241 (11)
H11A	1.0231	0.6050	0.0330	0.029*
H11B	1.1013	0.5297	0.0466	0.029*
C12	0.8357 (6)	0.5522 (3)	−0.01916 (18)	0.0325 (12)
H12A	0.8543	0.6062	−0.0208	0.039*
H12B	0.7508	0.5445	−0.0008	0.039*
C13	0.8066 (5)	0.5223 (3)	−0.06456 (19)	0.0331 (13)
C14	0.7659 (5)	0.4457 (3)	−0.06974 (18)	0.0298 (12)
C15	0.7326 (4)	0.4179 (3)	−0.11206 (17)	0.0224 (10)
C16	0.7407 (5)	0.4668 (3)	−0.14761 (17)	0.0213 (10)
H16	0.7120	0.4492	−0.1752	0.026*
C17	0.7899 (5)	0.5413 (3)	−0.14414 (18)	0.0270 (11)
C18	0.8173 (6)	0.5681 (3)	−0.10158 (18)	0.0341 (13)
H18	0.8437	0.6186	−0.0979	0.041*
C19	0.7949 (5)	0.5958 (3)	−0.18339 (17)	0.0248 (11)
C20	0.6714 (6)	0.6530 (4)	−0.1800 (2)	0.0394 (14)
H20A	0.6761	0.6875	−0.2045	0.059*
H20B	0.6800	0.6808	−0.1529	0.059*
H20C	0.5802	0.6267	−0.1805	0.059*
C21	0.7839 (6)	0.5554 (3)	−0.22760 (18)	0.0362 (13)
H21A	0.8601	0.5186	−0.2299	0.054*
H21B	0.7930	0.5917	−0.2510	0.054*
H21C	0.6917	0.5305	−0.2297	0.054*
C22	0.9406 (6)	0.6384 (4)	−0.1838 (2)	0.0409 (15)
H22A	1.0187	0.6026	−0.1816	0.061*
H22B	0.9444	0.6727	−0.1592	0.061*
H22C	0.9495	0.6664	−0.2109	0.061*
C23	0.6772 (5)	0.3363 (3)	−0.11966 (17)	0.0219 (11)
H23A	0.7044	0.3198	−0.1491	0.026*
H23B	0.7229	0.3025	−0.0986	0.026*
C24	0.5149 (4)	0.3311 (3)	−0.11476 (17)	0.0193 (10)
C25	0.4507 (5)	0.3134 (3)	−0.07492 (16)	0.0192 (10)
C26	0.3010 (5)	0.3069 (3)	−0.06974 (16)	0.0217 (11)
C27	0.2140 (5)	0.3194 (3)	−0.10703 (16)	0.0212 (11)
H27	0.1138	0.3171	−0.1039	0.025*
C28	0.2714 (5)	0.3352 (3)	−0.14866 (16)	0.0189 (10)
C29	0.4241 (5)	0.3412 (3)	−0.15117 (16)	0.0183 (10)
H29	0.4660	0.3524	−0.1783	0.022*
C30	0.1784 (5)	0.3469 (3)	−0.18981 (16)	0.0208 (10)
C31	0.1912 (7)	0.4284 (3)	−0.2056 (2)	0.0431 (15)
H31A	0.1353	0.4349	−0.2320	0.065*
H31B	0.2910	0.4399	−0.2115	0.065*
H31C	0.1552	0.4619	−0.1831	0.065*
C32	0.0196 (5)	0.3289 (4)	−0.1811 (2)	0.0383 (14)
H32A	−0.0132	0.3570	−0.1559	0.057*
H32B	0.0090	0.2756	−0.1756	0.057*
H32C	−0.0371	0.3428	−0.2065	0.057*
C33	0.2310 (6)	0.2940 (4)	−0.22643 (18)	0.0367 (13)
H33A	0.1795	0.3049	−0.2532	0.055*
H33B	0.2135	0.2424	−0.2180	0.055*
H33C	0.3329	0.3014	−0.2311	0.055*
C34	0.2330 (5)	0.2775 (3)	−0.02779 (16)	0.0261 (11)
H34A	0.1331	0.2945	−0.0265	0.031*
H34B	0.2320	0.2225	−0.0288	0.031*
C35	0.2599 (5)	0.3735 (3)	0.02840 (16)	0.0231 (11)
H35A	0.1549	0.3769	0.0280	0.028*
H35B	0.2987	0.4139	0.0101	0.028*
C36	0.3156 (4)	0.3808 (3)	0.07508 (16)	0.0205 (10)
C37	0.4671 (5)	0.3848 (3)	0.08268 (16)	0.0200 (10)
C38	0.5191 (4)	0.3881 (3)	0.12493 (16)	0.0182 (10)
C39	0.4223 (5)	0.3924 (3)	0.16034 (17)	0.0208 (10)
H39	0.4592	0.3965	0.1888	0.025*
C40	0.2698 (5)	0.3907 (3)	0.15439 (15)	0.0195 (10)
C41	0.2207 (5)	0.3855 (3)	0.11068 (16)	0.0225 (10)
H41	0.1214	0.3853	0.1053	0.027*
C42	0.1647 (5)	0.4005 (3)	0.19308 (16)	0.0228 (11)
C43	0.1035 (5)	0.4799 (3)	0.1916 (2)	0.0311 (13)
H43A	0.0283	0.4848	0.2133	0.047*
H43B	0.0643	0.4896	0.1628	0.047*
H43C	0.1792	0.5157	0.1978	0.047*
C44	0.2381 (5)	0.3865 (3)	0.23702 (15)	0.0253 (11)
H44A	0.2814	0.3370	0.2370	0.038*
H44B	0.1676	0.3895	0.2603	0.038*
H44C	0.3118	0.4240	0.2417	0.038*
C45	0.0403 (5)	0.3421 (3)	0.18882 (19)	0.0322 (12)
H45A	0.0796	0.2917	0.1900	0.048*
H45B	−0.0087	0.3493	0.1612	0.048*
H45C	−0.0271	0.3490	0.2126	0.048*
C46	0.6821 (5)	0.3889 (3)	0.13465 (17)	0.0212 (10)
H46A	0.6972	0.3771	0.1656	0.025*
H46B	0.7287	0.3496	0.1173	0.025*
C47	0.4073 (9)	0.6656 (5)	0.0445 (3)	0.073 (2)
H47	0.3665	0.6632	0.0147	0.087*
Cl1	0.2803 (3)	0.70978 (15)	0.07854 (10)	0.1005 (9)
Cl2	0.5685 (3)	0.71738 (15)	0.04176 (9)	0.0934 (8)
Cl3	0.4431 (3)	0.57232 (12)	0.06175 (9)	0.0862 (7)
O7	0.3201 (5)	0.6469 (3)	−0.05420 (16)	0.0573 (13)
C48	0.1989 (8)	0.6047 (4)	−0.0688 (3)	0.067 (2)
H48A	0.1481	0.6328	−0.0916	0.080*
H48B	0.1326	0.5969	−0.0443	0.080*
C49	0.2451 (12)	0.5324 (7)	−0.0860 (4)	0.109 (3)
H49A	0.2164	0.4916	−0.0664	0.131*
H49B	0.2038	0.5234	−0.1150	0.131*
C50	0.3989 (12)	0.5381 (7)	−0.0884 (5)	0.118 (3)
H50A	0.4294	0.5323	−0.1189	0.141*
H50B	0.4422	0.4974	−0.0714	0.141*
C51	0.4506 (10)	0.6109 (6)	−0.0715 (4)	0.091 (3)
H51A	0.5220	0.6036	−0.0484	0.110*
H51B	0.4931	0.6411	−0.0950	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0215 (15)	0.0262 (18)	0.0196 (19)	−0.0027 (13)	0.0050 (13)	−0.0064 (15)
O2	0.0301 (17)	0.0293 (19)	0.0182 (19)	−0.0059 (15)	−0.0014 (15)	−0.0016 (15)
O3	0.0424 (19)	0.033 (2)	0.030 (2)	−0.0093 (16)	−0.0027 (17)	0.0054 (17)
O4	0.0239 (16)	0.0267 (19)	0.0192 (19)	0.0036 (14)	−0.0009 (14)	−0.0009 (15)
O5	0.0297 (17)	0.0235 (18)	0.0195 (19)	−0.0008 (14)	−0.0031 (14)	−0.0058 (15)
O6	0.0208 (15)	0.0293 (19)	0.0139 (17)	−0.0055 (14)	0.0002 (13)	−0.0005 (15)
C1	0.015 (2)	0.017 (2)	0.026 (3)	−0.0002 (17)	−0.0071 (19)	−0.003 (2)
C2	0.0132 (19)	0.024 (3)	0.017 (2)	−0.0007 (18)	−0.0046 (18)	0.001 (2)
C3	0.019 (2)	0.024 (3)	0.022 (3)	−0.0026 (19)	0.0044 (19)	0.001 (2)
C4	0.028 (2)	0.024 (3)	0.017 (3)	0.0006 (19)	−0.001 (2)	−0.004 (2)
C5	0.027 (2)	0.017 (2)	0.020 (3)	−0.0090 (18)	−0.001 (2)	0.001 (2)
C6	0.017 (2)	0.026 (3)	0.017 (3)	−0.0030 (18)	0.0003 (18)	−0.002 (2)
C7	0.037 (3)	0.025 (3)	0.032 (3)	−0.002 (2)	0.003 (2)	−0.002 (2)
C8	0.100 (6)	0.050 (4)	0.050 (5)	0.020 (4)	−0.036 (4)	−0.019 (4)
C9	0.058 (4)	0.041 (4)	0.073 (5)	0.001 (3)	0.038 (4)	−0.015 (4)
C10	0.091 (5)	0.025 (3)	0.044 (4)	−0.006 (3)	0.022 (4)	−0.007 (3)
C11	0.027 (2)	0.033 (3)	0.013 (3)	−0.010 (2)	0.0002 (19)	−0.002 (2)
C12	0.038 (3)	0.033 (3)	0.026 (3)	−0.003 (2)	−0.004 (2)	−0.006 (2)
C13	0.031 (3)	0.036 (3)	0.032 (3)	−0.001 (2)	0.000 (2)	−0.001 (3)
C14	0.030 (3)	0.032 (3)	0.027 (3)	−0.003 (2)	0.001 (2)	0.002 (2)
C15	0.017 (2)	0.025 (3)	0.025 (3)	−0.0045 (19)	−0.0021 (19)	0.002 (2)
C16	0.015 (2)	0.025 (3)	0.023 (3)	−0.0005 (19)	0.0002 (19)	0.000 (2)
C17	0.028 (3)	0.028 (3)	0.025 (3)	−0.004 (2)	−0.006 (2)	0.002 (2)
C18	0.042 (3)	0.034 (3)	0.026 (3)	−0.007 (2)	−0.001 (2)	0.011 (2)
C19	0.028 (2)	0.023 (3)	0.023 (3)	0.002 (2)	0.001 (2)	0.004 (2)
C20	0.035 (3)	0.052 (4)	0.031 (3)	0.016 (3)	−0.001 (3)	0.008 (3)
C21	0.053 (3)	0.035 (3)	0.020 (3)	0.003 (3)	0.002 (3)	0.003 (2)
C22	0.040 (3)	0.049 (4)	0.034 (4)	−0.011 (3)	−0.001 (3)	0.008 (3)
C23	0.022 (2)	0.018 (2)	0.026 (3)	−0.0032 (19)	0.000 (2)	−0.002 (2)
C24	0.021 (2)	0.010 (2)	0.027 (3)	−0.0019 (17)	−0.002 (2)	−0.001 (2)
C25	0.023 (2)	0.016 (2)	0.018 (3)	0.0026 (18)	−0.004 (2)	−0.0004 (19)
C26	0.023 (2)	0.023 (3)	0.019 (3)	−0.0059 (19)	0.001 (2)	0.002 (2)
C27	0.022 (2)	0.022 (3)	0.020 (3)	−0.0015 (18)	0.0025 (19)	−0.004 (2)
C28	0.022 (2)	0.017 (2)	0.018 (3)	−0.0029 (19)	−0.0029 (19)	−0.001 (2)
C29	0.020 (2)	0.019 (2)	0.015 (3)	0.0033 (18)	0.0041 (18)	−0.002 (2)
C30	0.018 (2)	0.022 (3)	0.022 (3)	0.0009 (18)	0.0019 (19)	0.000 (2)
C31	0.052 (3)	0.033 (3)	0.045 (4)	−0.004 (3)	−0.013 (3)	0.006 (3)
C32	0.029 (3)	0.057 (4)	0.029 (3)	−0.009 (2)	−0.006 (2)	0.012 (3)
C33	0.040 (3)	0.047 (3)	0.022 (3)	0.006 (3)	−0.011 (2)	−0.008 (3)
C34	0.027 (2)	0.031 (3)	0.020 (3)	−0.008 (2)	−0.003 (2)	−0.001 (2)
C35	0.019 (2)	0.031 (3)	0.019 (3)	0.004 (2)	−0.004 (2)	−0.006 (2)
C36	0.017 (2)	0.022 (3)	0.022 (3)	0.0018 (19)	−0.0039 (19)	−0.004 (2)
C37	0.019 (2)	0.018 (2)	0.023 (3)	0.0002 (19)	0.0040 (19)	−0.003 (2)
C38	0.017 (2)	0.019 (3)	0.018 (3)	−0.0014 (18)	−0.0019 (18)	0.005 (2)
C39	0.026 (2)	0.016 (2)	0.020 (3)	0.0013 (19)	−0.006 (2)	0.000 (2)
C40	0.019 (2)	0.019 (2)	0.021 (3)	−0.0060 (18)	−0.0015 (18)	−0.002 (2)
C41	0.020 (2)	0.025 (3)	0.023 (3)	−0.0010 (19)	−0.0008 (19)	0.001 (2)
C42	0.022 (2)	0.024 (3)	0.021 (3)	−0.0059 (19)	0.0011 (19)	−0.006 (2)
C43	0.022 (2)	0.035 (3)	0.036 (3)	0.007 (2)	−0.002 (2)	−0.009 (3)
C44	0.028 (2)	0.031 (3)	0.017 (3)	0.003 (2)	0.004 (2)	−0.003 (2)
C45	0.028 (2)	0.039 (3)	0.030 (3)	−0.013 (2)	0.006 (2)	−0.007 (3)
C46	0.017 (2)	0.022 (3)	0.024 (3)	−0.0003 (19)	−0.0051 (19)	0.001 (2)
C47	0.082 (5)	0.053 (5)	0.082 (6)	0.002 (4)	−0.030 (5)	−0.002 (4)
Cl1	0.0882 (15)	0.0866 (16)	0.127 (2)	−0.0010 (13)	0.0001 (14)	−0.0468 (16)
Cl2	0.0961 (16)	0.0803 (16)	0.1037 (19)	−0.0264 (13)	−0.0120 (14)	0.0019 (14)
Cl3	0.0915 (14)	0.0536 (12)	0.113 (2)	−0.0001 (10)	−0.0220 (14)	0.0112 (12)
O7	0.041 (2)	0.067 (3)	0.064 (3)	0.006 (2)	−0.002 (2)	−0.013 (3)
C48	0.065 (3)	0.063 (3)	0.073 (4)	−0.007 (3)	0.007 (3)	−0.005 (3)
C49	0.108 (4)	0.106 (4)	0.114 (4)	0.007 (4)	−0.004 (4)	−0.014 (4)
C50	0.113 (4)	0.115 (4)	0.125 (5)	0.011 (4)	0.020 (4)	−0.009 (4)
C51	0.077 (4)	0.106 (4)	0.091 (4)	0.003 (4)	0.008 (3)	0.007 (4)

Geometric parameters (Å, º)

O1—C1	1.402 (6)	C23—C24	1.507 (6)
O2—C12	1.401 (6)	C24—C25	1.380 (7)
O2—C11	1.425 (6)	C24—C29	1.396 (7)
O3—C14	1.352 (6)	C25—C26	1.394 (6)
O4—C25	1.398 (6)	C26—C27	1.403 (7)
O5—C35	1.436 (6)	C26—C34	1.509 (7)
O5—C34	1.438 (6)	C27—C28	1.396 (7)
O6—C37	1.367 (6)	C28—C29	1.415 (6)
C1—C2	1.381 (6)	C28—C30	1.527 (7)
C1—C6	1.402 (7)	C30—C31	1.519 (8)
C2—C3	1.387 (7)	C30—C33	1.529 (7)
C2—C46	1.519 (7)	C30—C32	1.521 (7)
C3—C4	1.401 (7)	C35—C36	1.510 (7)
C4—C5	1.401 (7)	C36—C41	1.392 (7)
C4—C7	1.523 (7)	C36—C37	1.418 (6)
C5—C6	1.395 (7)	C37—C38	1.367 (7)
C6—C11	1.516 (6)	C38—C39	1.397 (7)
C7—C8	1.505 (9)	C38—C46	1.532 (6)
C7—C10	1.515 (8)	C39—C40	1.418 (6)
C7—C9	1.550 (8)	C40—C41	1.402 (7)
C12—C13	1.497 (8)	C40—C42	1.531 (7)
C13—C18	1.386 (8)	C42—C43	1.511 (7)
C13—C14	1.410 (8)	C42—C44	1.513 (7)
C14—C15	1.407 (7)	C42—C45	1.547 (7)
C15—C16	1.382 (7)	C47—Cl1	1.744 (9)
C15—C23	1.545 (7)	C47—Cl2	1.748 (9)
C16—C17	1.394 (7)	C47—Cl3	1.758 (8)
C17—C18	1.396 (8)	O7—C48	1.413 (9)
C17—C19	1.529 (7)	O7—C51	1.458 (10)
C19—C21	1.519 (7)	C48—C49	1.442 (14)
C19—C20	1.526 (7)	C49—C50	1.425 (14)
C19—C22	1.540 (7)	C50—C51	1.462 (16)
C12—O2—C11	114.2 (4)	C24—C25—C26	122.8 (4)
C35—O5—C34	114.3 (3)	C24—C25—O4	117.6 (4)
C2—C1—C6	121.7 (4)	C26—C25—O4	119.6 (4)
C2—C1—O1	118.0 (4)	C25—C26—C27	117.6 (4)
C6—C1—O1	120.3 (4)	C25—C26—C34	122.3 (4)
C1—C2—C3	117.9 (4)	C27—C26—C34	119.6 (4)
C1—C2—C46	121.3 (4)	C28—C27—C26	122.8 (4)
C3—C2—C46	120.8 (4)	C27—C28—C29	116.2 (4)
C2—C3—C4	123.5 (4)	C27—C28—C30	123.5 (4)
C3—C4—C5	116.3 (4)	C29—C28—C30	120.4 (4)
C3—C4—C7	121.3 (4)	C24—C29—C28	123.0 (4)
C5—C4—C7	122.4 (4)	C31—C30—C33	109.0 (5)
C6—C5—C4	122.2 (4)	C31—C30—C32	109.1 (4)
C5—C6—C1	118.3 (4)	C33—C30—C32	107.6 (4)
C5—C6—C11	120.3 (4)	C31—C30—C28	109.9 (4)
C1—C6—C11	121.3 (4)	C33—C30—C28	109.3 (4)
C8—C7—C10	111.6 (5)	C32—C30—C28	111.8 (4)
C8—C7—C4	110.1 (5)	O5—C34—C26	114.1 (4)
C10—C7—C4	112.6 (5)	O5—C35—C36	107.6 (4)
C8—C7—C9	108.2 (6)	C41—C36—C37	119.4 (4)
C10—C7—C9	104.8 (5)	C41—C36—C35	121.1 (4)
C4—C7—C9	109.3 (5)	C37—C36—C35	119.5 (4)
O2—C11—C6	112.7 (4)	C38—C37—O6	124.4 (4)
O2—C12—C13	111.0 (4)	C38—C37—C36	120.0 (4)
C18—C13—C14	119.2 (5)	O6—C37—C36	115.6 (4)
C18—C13—C12	121.6 (5)	C37—C38—C39	119.7 (4)
C14—C13—C12	119.2 (5)	C37—C38—C46	121.6 (4)
O3—C14—C15	123.9 (5)	C39—C38—C46	118.6 (4)
O3—C14—C13	116.4 (5)	C38—C39—C40	122.3 (5)
C15—C14—C13	119.6 (5)	C41—C40—C39	116.2 (4)
C16—C15—C14	118.6 (4)	C41—C40—C42	121.6 (4)
C16—C15—C23	118.9 (4)	C39—C40—C42	121.9 (4)
C14—C15—C23	122.3 (4)	C40—C41—C36	122.1 (4)
C15—C16—C17	123.2 (5)	C43—C42—C44	110.1 (4)
C16—C17—C18	116.6 (5)	C43—C42—C40	108.6 (4)
C16—C17—C19	122.9 (5)	C44—C42—C40	111.8 (4)
C18—C17—C19	119.9 (5)	C43—C42—C45	109.8 (4)
C13—C18—C17	122.4 (5)	C44—C42—C45	107.2 (4)
C17—C19—C21	112.9 (4)	C40—C42—C45	109.3 (4)
C17—C19—C20	109.9 (4)	C2—C46—C38	113.2 (4)
C21—C19—C20	108.6 (4)	Cl1—C47—Cl2	111.5 (5)
C17—C19—C22	109.9 (4)	Cl1—C47—Cl3	111.7 (5)
C21—C19—C22	106.2 (4)	Cl2—C47—Cl3	110.1 (4)
C20—C19—C22	109.2 (4)	C48—O7—C51	108.2 (6)
C24—C23—C15	111.7 (4)	O7—C48—C49	110.1 (7)
C25—C24—C29	117.5 (4)	C50—C49—C48	104.5 (10)
C25—C24—C23	121.8 (4)	C49—C50—C51	111.6 (10)
C29—C24—C23	120.7 (4)	O7—C51—C50	103.8 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	2.00	2.699 (8)	140
O1—H1···O3	0.84	2.41	2.870 (8)	116
O3—H3···O4	0.94	1.83	2.712 (8)	154
O4—H4···O5	1.05	1.75	2.662 (8)	143
O4—H4···O6	1.05	2.32	2.939 (8)	117
O6—H6···O1	0.93	1.91	2.833 (8)	177
C47—H47···O7	0.98	2.15	3.113 (10)	168