Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705012X/hg2307sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705012X/hg2307Isup2.hkl |
CCDC reference: 662145
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.003 Å
- H-atom completeness 100%
- Disorder in solvent or counterion
- R factor = 0.058
- wR factor = 0.175
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.32 Ratio
Author Response: Explained in the text of the _publ_section_exptl_refinement section. |
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.25 Ratio
Author Response: Explained in the text of the _publ_section_exptl_refinement section. |
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O9 - H9 ... ?
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.785 0.960 Tmin(prime) and Tmax expected: 0.947 0.960 RR(prime) = 0.829 Please check that your absorption correction is appropriate. DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.666 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.67 e/A PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C62 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 1.00 Perc. PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O1W PLAT414_ALERT_2_C Short Intra D-H..H-X H8 .. H64A .. 1.92 Ang.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C69 H84.21 O13.103 Atom count from the _atom_site data: C69 H84 O13.10299 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C69 H84.21 O13.103 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 276.00 276.00 0.00 H 336.84 336.00 0.84 O 52.41 52.41 0.00 PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C23 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C39 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C55 = ... R
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2-Methylresorcinol (12.41 g, 0.10 mol) was added to a stirred mixture of water (100 ml), ethanol (200 ml) and 32% aqueous HCl (50 ml). The reaction vessel and its contents were cooled to a temperature in the range of 273–278 K, by immersion in an ice-salt bath before 3-phenylpropionaldehyde (13.42 g, 0.10 mol) was added slowly over 30 minutes. Once addition was complete, the solution was allowed to slowly attain room temperature, after which time it was refluxed at 353 K for 48 h. The solution was cooled to room temperature, and water added in order to precipitate out the crude product. The brown material that separated was filtered from the solution, washed with cold 1:1 e thanol:water until the washings were light yellow and then redissolved in warm methanol and recrystallized overnight. The resulting peach-coloured material was then filtered from the methanol solution and thereafter stirred in hexane to remove residual aldehyde. The solid was filtered from hexane and dried, to yield the title compound as a peach-coloured microcrystalline solid. (13.93 g, 58%). mp 555–559 K. 1H NMR [d6-DMSO, 300 MHz]: d= 1.97 (s, 12 H, Ar CH3), 2.49–2.50 (m, 28 H, CH2CH2Ar, and DMSO as solvent signal), 4.26–4.30 (t, J = 7.0 Hz, 4 H, CHCH2), 7.13–7.29 (m, 20 H, C6H5), 7.39 (s, 4 H, Ar H), 8.73 (s, 8 H, OH). 13C NMR [CDCl3, 75 MHz]: d = 149.34, 142.40, 128.70, 128.38, 125.81, 125.00, 111.88, 40.533, 40.250, 39.134, 38.859, 10.264. Anal Calcd for C64H64O8 (961.195): C 79.97, H 6.71. Found: C 80.42, H 6.79.
A solution of the compound in hot methanol, subsequently cooled in a refrigerator at 277 K, provided crystals suitable for X-ray crystallography.
In the final stages of refinement H atoms were placed in calculated positions with C—H distances of 0.95, 0.98, 0.99 and 1.00 Å for H bonded to aryl, methyl, methylene and tertiary C atoms, respectively, and at O—H distances of 0.84 Å. They were than refined with a riding model with Uiso(H) = 1.5Ueq(X) for X = O or methyl C and Uiso(H) = 1.2Ueq(C) otherwise. The torsion angles of the methyl and hydroxyl groups were also refined. The atom O1W was introduced into the structural model to account for an electron density feature of approximately 1 e/Å3. Its coordinates and sof were refined with its Uiso fixed, somewhat arbitrarily, at 0.05. This feature is interpreted as the O atom of a water molecule but its low occupancy factor [0.103 (5)] has prevented discovery of the associated H atoms which are, therefore, absent from the structural model. Rather large and significantly anisotropic displacement parameters for atoms C60—C62 are indicative of libration in this part of the molecule. The largest residual electron density peak of 0.67 e/Å3 is 0.94 Å from C11.
In the title compound, (I), the [4]arene moiety, (I A), is a cyclic tetramer. The labelling scheme for one of the monomers, shown in Fig.1, extends over the whole molecule such that for monomer n the numbers p and q associated with particular C and O atoms, respectively, become p' = p + 16 x (n - 1) and q' = q + 2 x (n - 1). The asymmetric unit of (I) is shown in Fig. 2. The bond lengths and bond angles all fall within the normal ranges and are not discussed further. In molecule (I A) the 2-phenylethyl 'feet' all lie to one side of the macrocyclic ring surrounding the site of the partially occupied water molecule, O1W, with their phenyl groups in a cyclic edge-to-face arrangement. All but one of the OH groups participate in O—H···O hydrogen-bond formation (Table 1) and all but three of those listed occur within the asymmetric unit (Fig.2). The acceptor for methanolic O9 is the benzene ring, with centroid Cg, defined by C17—C22. The parameters for this O—H..π contact include the H..Cg distance and O—H..Cg angle of 2.48 Å and 173°, respectively. The O2—H2.·O6i (symmetry code as in Table 1) hydrogen-bond provides direct connection between molecules (1 A) in the propagation of chains in the direction of the cell edge a. The hydrogen-bonds O7—H7.·O9ii and O10—H10.·O13ii link chains, related to one another by crystallographic centres of symmetry, in pairs as shown in Fig. 3.
The partial occupancy of the water molecule associated with (I) is not exclusive to this structure, and has been noted before in related structures. For related literature, see Tunstad et al. (1989) and Cram et al. (1988).
For related literature, see: Cram et al. (1988); Tunstad et al. (1989).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
C64H64O8·5CH4O·0.103H2O | F(000) = 2412 |
Mr = 1123.22 | Dx = 1.201 Mg m−3 |
Monoclinic, P21/n | Melting point = 555–559 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.3109 (3) Å | Cell parameters from 39787 reflections |
b = 30.6151 (7) Å | θ = 3.7–34.1° |
c = 16.5024 (3) Å | µ = 0.08 mm−1 |
β = 92.8385 (19)° | T = 105 K |
V = 6212.1 (2) Å3 | Block, light orange |
Z = 4 | 0.65 × 0.50 × 0.50 mm |
Oxford Xcalibur-2 area-detector diffractometer | 14218 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 10324 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 0 pixels mm-1 | θmax = 27.5°, θmin = 3.7° |
φ and ω scans | h = −15→15 |
Absorption correction: multi-scan [empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm of CrysAlis RED (Oxford Diffraction, 2006)] | k = −39→39 |
Tmin = 0.785, Tmax = 0.960 | l = −21→21 |
74273 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0811P)2 + 4.858P] where P = (Fo2 + 2Fc2)/3 |
14218 reflections | (Δ/σ)max = 0.001 |
765 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C64H64O8·5CH4O·0.103H2O | V = 6212.1 (2) Å3 |
Mr = 1123.22 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.3109 (3) Å | µ = 0.08 mm−1 |
b = 30.6151 (7) Å | T = 105 K |
c = 16.5024 (3) Å | 0.65 × 0.50 × 0.50 mm |
β = 92.8385 (19)° |
Oxford Xcalibur-2 area-detector diffractometer | 14218 independent reflections |
Absorption correction: multi-scan [empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm of CrysAlis RED (Oxford Diffraction, 2006)] | 10324 reflections with I > 2σ(I) |
Tmin = 0.785, Tmax = 0.960 | Rint = 0.028 |
74273 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.67 e Å−3 |
14218 reflections | Δρmin = −0.39 e Å−3 |
765 parameters |
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. O—H..pi geometry (extract from PLATON output listing) O—H H.·Cg H-Perp Gamma O—H.·Cg O.·Cg O—H,Pi O9—H9.·Cg 0.84 2.48 2.409 13.89 173 3.3182 (18) 80 Cg is the centroid of the ring defined by C17—C22 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.85729 (11) | 0.09144 (5) | 0.32812 (8) | 0.0246 (3) | |
H1 | 0.7916 | 0.0919 | 0.3116 | 0.037* | |
O2 | 1.03772 (12) | 0.08075 (5) | 0.59094 (9) | 0.0300 (3) | |
H2 | 1.0931 | 0.0746 | 0.5655 | 0.045* | |
O3 | 0.96781 (12) | 0.05706 (5) | 0.73621 (9) | 0.0286 (3) | |
H3 | 0.9920 | 0.0671 | 0.6933 | 0.043* | |
O4 | 0.63258 (12) | 0.03653 (5) | 0.85613 (8) | 0.0252 (3) | |
H4 | 0.5664 | 0.0424 | 0.8474 | 0.038* | |
O5 | 0.40942 (12) | 0.04559 (5) | 0.81674 (9) | 0.0273 (3) | |
H5 | 0.3490 | 0.0392 | 0.8351 | 0.041* | |
O6 | 0.23362 (10) | 0.05510 (4) | 0.55231 (8) | 0.0210 (3) | |
H6 | 0.2554 | 0.0596 | 0.5056 | 0.032* | |
O7 | 0.30719 (11) | 0.06709 (4) | 0.40248 (8) | 0.0227 (3) | |
H7 | 0.3129 | 0.0413 | 0.3856 | 0.034* | |
O8 | 0.64617 (12) | 0.09095 (5) | 0.27331 (8) | 0.0260 (3) | |
H8 | 0.6123 | 0.0842 | 0.2296 | 0.039* | |
O9 | 0.70597 (16) | 0.01875 (5) | 0.60865 (10) | 0.0411 (4) | |
H9 | 0.7256 | 0.0358 | 0.6465 | 0.062* | |
O10 | 0.23037 (16) | 0.03459 (6) | 0.89641 (11) | 0.0454 (4) | |
H10 | 0.2039 | 0.0095 | 0.9020 | 0.068* | |
O11 | 0.98560 (14) | 0.07699 (6) | 0.20163 (12) | 0.0434 (4) | |
H11 | 0.9627 | 0.0846 | 0.2466 | 0.065* | |
O12 | 0.62774 (17) | 0.06765 (7) | 0.11976 (11) | 0.0535 (5) | |
H12 | 0.6909 | 0.0610 | 0.1071 | 0.080* | |
O13 | 0.84004 (16) | 0.05017 (6) | 0.08692 (11) | 0.0468 (5) | |
H13 | 0.8876 | 0.0562 | 0.1235 | 0.070* | |
O1W | 0.6027 (15) | 0.2344 (6) | 0.6306 (12) | 0.050* | 0.103 (5) |
C1 | 0.80760 (15) | 0.14614 (6) | 0.51960 (11) | 0.0188 (4) | |
H1A | 0.7578 | 0.1662 | 0.5413 | 0.023* | |
C2 | 0.79593 (15) | 0.13561 (6) | 0.43786 (11) | 0.0184 (4) | |
C3 | 0.86596 (15) | 0.10398 (6) | 0.40833 (11) | 0.0187 (4) | |
C4 | 0.94785 (15) | 0.08440 (6) | 0.45757 (12) | 0.0197 (4) | |
C5 | 0.95919 (15) | 0.09790 (6) | 0.53830 (12) | 0.0208 (4) | |
C6 | 0.88912 (15) | 0.12854 (6) | 0.57123 (11) | 0.0198 (4) | |
C7 | 0.90150 (15) | 0.14173 (6) | 0.66068 (11) | 0.0200 (4) | |
H7A | 0.9787 | 0.1361 | 0.6793 | 0.024* | |
C8 | 0.87922 (16) | 0.19076 (6) | 0.67358 (12) | 0.0224 (4) | |
H8A | 0.8028 | 0.1970 | 0.6557 | 0.027* | |
H8B | 0.8875 | 0.1972 | 0.7323 | 0.027* | |
C9 | 0.95389 (17) | 0.22143 (7) | 0.62824 (13) | 0.0266 (4) | |
H9A | 1.0263 | 0.2222 | 0.6572 | 0.032* | |
H9B | 0.9635 | 0.2097 | 0.5732 | 0.032* | |
C10 | 0.90986 (17) | 0.26746 (7) | 0.62107 (12) | 0.0251 (4) | |
C11 | 0.9589 (2) | 0.30254 (9) | 0.66018 (17) | 0.0498 (7) | |
H11A | 1.0245 | 0.2981 | 0.6919 | 0.060* | |
C12 | 0.9150 (3) | 0.34435 (9) | 0.6546 (2) | 0.0586 (8) | |
H12A | 0.9489 | 0.3674 | 0.6848 | 0.070* | |
C13 | 0.8263 (2) | 0.35265 (8) | 0.60759 (17) | 0.0451 (6) | |
H13A | 0.7988 | 0.3816 | 0.6026 | 0.054* | |
C14 | 0.7747 (3) | 0.31839 (10) | 0.5659 (2) | 0.0648 (9) | |
H14 | 0.7111 | 0.3236 | 0.5324 | 0.078* | |
C15 | 0.8169 (3) | 0.27649 (9) | 0.5738 (2) | 0.0576 (8) | |
H15 | 0.7806 | 0.2532 | 0.5456 | 0.069* | |
C16 | 1.02018 (16) | 0.04978 (7) | 0.42312 (12) | 0.0242 (4) | |
H16A | 1.0795 | 0.0638 | 0.3955 | 0.036* | |
H16B | 0.9773 | 0.0317 | 0.3843 | 0.036* | |
H16C | 1.0505 | 0.0314 | 0.4672 | 0.036* | |
C17 | 0.72402 (15) | 0.12586 (6) | 0.72762 (11) | 0.0197 (4) | |
H17 | 0.6972 | 0.1522 | 0.7038 | 0.024* | |
C18 | 0.82944 (15) | 0.11320 (6) | 0.71213 (11) | 0.0197 (4) | |
C19 | 0.86595 (16) | 0.07334 (6) | 0.74615 (11) | 0.0213 (4) | |
C20 | 0.79892 (16) | 0.04773 (6) | 0.79338 (11) | 0.0227 (4) | |
C21 | 0.69420 (16) | 0.06269 (6) | 0.80808 (11) | 0.0202 (4) | |
C22 | 0.65541 (15) | 0.10231 (6) | 0.77587 (11) | 0.0184 (4) | |
C23 | 0.54167 (15) | 0.11898 (6) | 0.79234 (11) | 0.0190 (4) | |
H23 | 0.5216 | 0.1063 | 0.8454 | 0.023* | |
C24 | 0.53656 (16) | 0.16896 (6) | 0.80089 (11) | 0.0217 (4) | |
H24A | 0.5586 | 0.1825 | 0.7497 | 0.026* | |
H24B | 0.4604 | 0.1777 | 0.8091 | 0.026* | |
C25 | 0.60952 (19) | 0.18671 (7) | 0.87140 (13) | 0.0289 (5) | |
H25A | 0.5798 | 0.1776 | 0.9234 | 0.035* | |
H25B | 0.6832 | 0.1740 | 0.8687 | 0.035* | |
C26 | 0.61727 (18) | 0.23588 (7) | 0.86898 (12) | 0.0278 (4) | |
C27 | 0.54097 (19) | 0.26162 (8) | 0.90601 (14) | 0.0337 (5) | |
H27 | 0.4835 | 0.2481 | 0.9330 | 0.040* | |
C28 | 0.5477 (2) | 0.30689 (8) | 0.90412 (15) | 0.0414 (6) | |
H28 | 0.4960 | 0.3241 | 0.9307 | 0.050* | |
C29 | 0.6291 (2) | 0.32680 (8) | 0.86384 (16) | 0.0455 (7) | |
H29 | 0.6333 | 0.3578 | 0.8624 | 0.055* | |
C30 | 0.7051 (2) | 0.30190 (9) | 0.82532 (17) | 0.0474 (6) | |
H30 | 0.7610 | 0.3156 | 0.7969 | 0.057* | |
C31 | 0.6987 (2) | 0.25636 (8) | 0.82873 (15) | 0.0394 (5) | |
H31 | 0.7512 | 0.2392 | 0.8029 | 0.047* | |
C32 | 0.8400 (2) | 0.00431 (7) | 0.82479 (14) | 0.0331 (5) | |
H32A | 0.8684 | −0.0126 | 0.7801 | 0.050* | |
H32B | 0.7802 | −0.0118 | 0.8481 | 0.050* | |
H32C | 0.8981 | 0.0090 | 0.8666 | 0.050* | |
C33 | 0.44583 (15) | 0.12271 (6) | 0.65276 (11) | 0.0180 (4) | |
H33 | 0.4909 | 0.1470 | 0.6417 | 0.022* | |
C34 | 0.45880 (15) | 0.10231 (6) | 0.72794 (11) | 0.0191 (4) | |
C35 | 0.39305 (15) | 0.06632 (6) | 0.74253 (11) | 0.0206 (4) | |
C36 | 0.31748 (15) | 0.05023 (6) | 0.68409 (12) | 0.0205 (4) | |
C37 | 0.30842 (14) | 0.07197 (6) | 0.60963 (11) | 0.0180 (4) | |
C38 | 0.36957 (15) | 0.10907 (6) | 0.59312 (11) | 0.0175 (4) | |
C39 | 0.34967 (14) | 0.13512 (6) | 0.51486 (11) | 0.0166 (3) | |
H39 | 0.2751 | 0.1273 | 0.4926 | 0.020* | |
C40 | 0.34971 (15) | 0.18472 (6) | 0.53140 (12) | 0.0203 (4) | |
H40A | 0.4218 | 0.1933 | 0.5555 | 0.024* | |
H40B | 0.3384 | 0.2004 | 0.4792 | 0.024* | |
C41 | 0.26174 (16) | 0.19876 (6) | 0.58852 (13) | 0.0241 (4) | |
H41A | 0.1893 | 0.1954 | 0.5605 | 0.029* | |
H41B | 0.2645 | 0.1795 | 0.6368 | 0.029* | |
C42 | 0.27684 (16) | 0.24562 (6) | 0.61530 (12) | 0.0224 (4) | |
C43 | 0.35539 (18) | 0.25666 (7) | 0.67442 (14) | 0.0316 (5) | |
H43 | 0.3986 | 0.2343 | 0.6996 | 0.038* | |
C44 | 0.3725 (2) | 0.29988 (8) | 0.69781 (15) | 0.0367 (5) | |
H44 | 0.4273 | 0.3068 | 0.7383 | 0.044* | |
C45 | 0.3100 (2) | 0.33255 (7) | 0.66223 (14) | 0.0355 (5) | |
H45 | 0.3214 | 0.3621 | 0.6780 | 0.043* | |
C46 | 0.2313 (2) | 0.32216 (8) | 0.60406 (16) | 0.0435 (6) | |
H46 | 0.1879 | 0.3446 | 0.5794 | 0.052* | |
C47 | 0.2143 (2) | 0.27888 (7) | 0.58070 (14) | 0.0359 (5) | |
H47 | 0.1590 | 0.2721 | 0.5405 | 0.043* | |
C48 | 0.24737 (17) | 0.01105 (7) | 0.69962 (13) | 0.0277 (4) | |
H48A | 0.2850 | −0.0080 | 0.7396 | 0.042* | |
H48B | 0.2333 | −0.0050 | 0.6488 | 0.042* | |
H48C | 0.1782 | 0.0207 | 0.7205 | 0.042* | |
C49 | 0.52746 (15) | 0.14412 (6) | 0.44485 (11) | 0.0171 (3) | |
H49 | 0.5457 | 0.1666 | 0.4828 | 0.021* | |
C50 | 0.42873 (15) | 0.12269 (6) | 0.45053 (11) | 0.0175 (4) | |
C51 | 0.40527 (15) | 0.08872 (6) | 0.39549 (11) | 0.0184 (4) | |
C52 | 0.47517 (15) | 0.07751 (6) | 0.33467 (11) | 0.0193 (4) | |
C53 | 0.57277 (15) | 0.10076 (6) | 0.33119 (11) | 0.0188 (4) | |
C54 | 0.60091 (15) | 0.13416 (6) | 0.38607 (11) | 0.0174 (4) | |
C55 | 0.70990 (15) | 0.15767 (6) | 0.38214 (11) | 0.0177 (4) | |
H55 | 0.7338 | 0.1543 | 0.3254 | 0.021* | |
C56 | 0.70088 (16) | 0.20715 (6) | 0.39854 (12) | 0.0208 (4) | |
H56A | 0.6709 | 0.2118 | 0.4524 | 0.025* | |
H56B | 0.7742 | 0.2205 | 0.3992 | 0.025* | |
C57 | 0.62734 (17) | 0.22929 (6) | 0.33338 (12) | 0.0252 (4) | |
H57A | 0.6613 | 0.2264 | 0.2805 | 0.030* | |
H57B | 0.5569 | 0.2136 | 0.3292 | 0.030* | |
C58 | 0.6057 (2) | 0.27697 (7) | 0.34883 (13) | 0.0317 (5) | |
C59 | 0.6691 (3) | 0.30944 (9) | 0.31820 (16) | 0.0539 (8) | |
H59 | 0.7307 | 0.3021 | 0.2885 | 0.065* | |
C60 | 0.6428 (4) | 0.35360 (10) | 0.3308 (2) | 0.0811 (14) | |
H60 | 0.6861 | 0.3759 | 0.3085 | 0.097* | |
C61 | 0.5566 (4) | 0.36466 (11) | 0.3742 (2) | 0.0849 (15) | |
H61 | 0.5404 | 0.3946 | 0.3831 | 0.102* | |
C62 | 0.4934 (3) | 0.33305 (14) | 0.4051 (3) | 0.0876 (15) | |
H62 | 0.4325 | 0.3409 | 0.4352 | 0.105* | |
C63 | 0.5171 (2) | 0.28891 (10) | 0.3929 (2) | 0.0554 (8) | |
H63 | 0.4725 | 0.2670 | 0.4149 | 0.066* | |
C64 | 0.44652 (17) | 0.04193 (7) | 0.27437 (13) | 0.0276 (4) | |
H64A | 0.4880 | 0.0461 | 0.2258 | 0.041* | |
H64B | 0.3685 | 0.0431 | 0.2595 | 0.041* | |
H64C | 0.4644 | 0.0134 | 0.2986 | 0.041* | |
C65 | 0.6480 (3) | 0.04221 (9) | 0.54767 (19) | 0.0532 (7) | |
H65A | 0.5834 | 0.0554 | 0.5701 | 0.080* | |
H65B | 0.6257 | 0.0224 | 0.5033 | 0.080* | |
H65C | 0.6945 | 0.0653 | 0.5270 | 0.080* | |
C66 | 0.2449 (3) | 0.05482 (11) | 0.97324 (17) | 0.0541 (7) | |
H66A | 0.2831 | 0.0826 | 0.9675 | 0.081* | |
H66B | 0.2879 | 0.0357 | 1.0100 | 0.081* | |
H66C | 0.1737 | 0.0602 | 0.9955 | 0.081* | |
C67 | 1.0729 (2) | 0.10443 (9) | 0.18161 (19) | 0.0473 (6) | |
H67A | 1.0485 | 0.1349 | 0.1805 | 0.071* | |
H67B | 1.0977 | 0.0963 | 0.1281 | 0.071* | |
H67C | 1.1330 | 0.1011 | 0.2224 | 0.071* | |
C68 | 0.5532 (3) | 0.05356 (11) | 0.05928 (16) | 0.0518 (7) | |
H68A | 0.5055 | 0.0314 | 0.0814 | 0.078* | |
H68B | 0.5921 | 0.0409 | 0.0145 | 0.078* | |
H68C | 0.5094 | 0.0784 | 0.0393 | 0.078* | |
C69 | 0.8670 (3) | 0.07095 (13) | 0.01281 (19) | 0.0721 (10) | |
H69A | 0.8737 | 0.1025 | 0.0216 | 0.108* | |
H69B | 0.8095 | 0.0652 | −0.0291 | 0.108* | |
H69C | 0.9361 | 0.0593 | −0.0048 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0263 (7) | 0.0256 (7) | 0.0220 (7) | −0.0026 (6) | 0.0011 (5) | −0.0051 (6) |
O2 | 0.0242 (7) | 0.0421 (9) | 0.0236 (7) | 0.0154 (7) | 0.0016 (6) | 0.0012 (6) |
O3 | 0.0277 (7) | 0.0281 (8) | 0.0304 (8) | 0.0100 (6) | 0.0045 (6) | 0.0046 (6) |
O4 | 0.0307 (7) | 0.0216 (7) | 0.0234 (7) | 0.0007 (6) | 0.0016 (6) | 0.0044 (5) |
O5 | 0.0289 (7) | 0.0278 (8) | 0.0253 (7) | −0.0037 (6) | 0.0015 (6) | 0.0084 (6) |
O6 | 0.0196 (6) | 0.0204 (7) | 0.0229 (7) | −0.0027 (5) | 0.0009 (5) | −0.0025 (5) |
O7 | 0.0232 (7) | 0.0178 (6) | 0.0272 (7) | −0.0045 (5) | 0.0026 (5) | −0.0070 (5) |
O8 | 0.0291 (7) | 0.0276 (8) | 0.0216 (7) | 0.0004 (6) | 0.0050 (6) | −0.0064 (6) |
O9 | 0.0655 (12) | 0.0222 (8) | 0.0349 (9) | −0.0091 (8) | −0.0030 (8) | −0.0058 (7) |
O10 | 0.0569 (11) | 0.0409 (10) | 0.0396 (10) | −0.0131 (9) | 0.0153 (8) | −0.0077 (8) |
O11 | 0.0363 (9) | 0.0382 (10) | 0.0570 (12) | 0.0048 (7) | 0.0150 (8) | −0.0054 (8) |
O12 | 0.0586 (12) | 0.0630 (13) | 0.0380 (10) | 0.0010 (10) | −0.0055 (9) | −0.0196 (9) |
O13 | 0.0572 (12) | 0.0488 (11) | 0.0350 (9) | −0.0158 (9) | 0.0092 (8) | −0.0053 (8) |
C1 | 0.0171 (8) | 0.0158 (8) | 0.0236 (9) | 0.0002 (7) | 0.0039 (7) | 0.0000 (7) |
C2 | 0.0184 (9) | 0.0136 (8) | 0.0231 (9) | −0.0022 (7) | 0.0010 (7) | 0.0016 (7) |
C3 | 0.0191 (9) | 0.0157 (8) | 0.0217 (9) | −0.0040 (7) | 0.0035 (7) | −0.0002 (7) |
C4 | 0.0187 (9) | 0.0156 (8) | 0.0249 (9) | −0.0016 (7) | 0.0038 (7) | 0.0003 (7) |
C5 | 0.0177 (9) | 0.0209 (9) | 0.0238 (9) | 0.0012 (7) | 0.0019 (7) | 0.0030 (7) |
C6 | 0.0195 (9) | 0.0194 (9) | 0.0206 (9) | −0.0015 (7) | 0.0027 (7) | −0.0002 (7) |
C7 | 0.0198 (9) | 0.0202 (9) | 0.0197 (9) | 0.0025 (7) | −0.0009 (7) | −0.0006 (7) |
C8 | 0.0240 (9) | 0.0207 (9) | 0.0225 (9) | −0.0017 (8) | 0.0020 (7) | −0.0019 (7) |
C9 | 0.0250 (10) | 0.0242 (10) | 0.0306 (11) | −0.0026 (8) | 0.0034 (8) | 0.0005 (8) |
C10 | 0.0281 (10) | 0.0223 (10) | 0.0251 (10) | −0.0039 (8) | 0.0020 (8) | −0.0001 (8) |
C11 | 0.0610 (17) | 0.0344 (13) | 0.0509 (16) | −0.0015 (12) | −0.0270 (13) | −0.0012 (11) |
C12 | 0.085 (2) | 0.0276 (13) | 0.0608 (18) | −0.0049 (14) | −0.0238 (16) | −0.0105 (12) |
C13 | 0.0567 (16) | 0.0236 (11) | 0.0555 (16) | 0.0038 (11) | 0.0073 (13) | 0.0057 (11) |
C14 | 0.0617 (19) | 0.0400 (16) | 0.089 (2) | 0.0092 (14) | −0.0299 (18) | 0.0011 (16) |
C15 | 0.0624 (18) | 0.0298 (13) | 0.077 (2) | 0.0014 (12) | −0.0309 (16) | −0.0089 (13) |
C16 | 0.0229 (9) | 0.0223 (10) | 0.0275 (10) | 0.0034 (8) | 0.0022 (8) | −0.0021 (8) |
C17 | 0.0244 (9) | 0.0170 (9) | 0.0176 (8) | 0.0021 (7) | −0.0012 (7) | 0.0002 (7) |
C18 | 0.0229 (9) | 0.0191 (9) | 0.0169 (8) | 0.0012 (7) | −0.0008 (7) | −0.0020 (7) |
C19 | 0.0238 (9) | 0.0206 (9) | 0.0193 (9) | 0.0051 (7) | −0.0016 (7) | −0.0031 (7) |
C20 | 0.0291 (10) | 0.0186 (9) | 0.0201 (9) | 0.0061 (8) | −0.0018 (8) | −0.0006 (7) |
C21 | 0.0270 (10) | 0.0180 (9) | 0.0155 (8) | −0.0006 (7) | −0.0007 (7) | −0.0011 (7) |
C22 | 0.0219 (9) | 0.0172 (9) | 0.0159 (8) | 0.0013 (7) | −0.0009 (7) | −0.0038 (7) |
C23 | 0.0232 (9) | 0.0165 (9) | 0.0173 (8) | 0.0015 (7) | 0.0008 (7) | −0.0002 (7) |
C24 | 0.0254 (10) | 0.0196 (9) | 0.0199 (9) | 0.0044 (7) | −0.0015 (7) | −0.0031 (7) |
C25 | 0.0412 (12) | 0.0199 (10) | 0.0247 (10) | 0.0055 (9) | −0.0069 (9) | −0.0057 (8) |
C26 | 0.0348 (11) | 0.0231 (10) | 0.0244 (10) | 0.0067 (8) | −0.0094 (8) | −0.0075 (8) |
C27 | 0.0365 (12) | 0.0324 (12) | 0.0314 (11) | 0.0104 (9) | −0.0077 (9) | −0.0073 (9) |
C28 | 0.0534 (15) | 0.0318 (12) | 0.0374 (13) | 0.0202 (11) | −0.0143 (11) | −0.0097 (10) |
C29 | 0.0700 (18) | 0.0222 (11) | 0.0417 (14) | 0.0085 (11) | −0.0220 (13) | −0.0077 (10) |
C30 | 0.0589 (17) | 0.0359 (14) | 0.0469 (15) | −0.0119 (12) | −0.0023 (13) | 0.0005 (11) |
C31 | 0.0466 (14) | 0.0303 (12) | 0.0413 (13) | 0.0022 (10) | 0.0031 (11) | −0.0106 (10) |
C32 | 0.0388 (12) | 0.0240 (11) | 0.0367 (12) | 0.0112 (9) | 0.0041 (10) | 0.0065 (9) |
C33 | 0.0189 (8) | 0.0150 (8) | 0.0204 (9) | −0.0003 (7) | 0.0027 (7) | −0.0025 (7) |
C34 | 0.0200 (9) | 0.0174 (9) | 0.0200 (9) | 0.0025 (7) | 0.0017 (7) | −0.0025 (7) |
C35 | 0.0223 (9) | 0.0189 (9) | 0.0208 (9) | 0.0029 (7) | 0.0029 (7) | 0.0011 (7) |
C36 | 0.0207 (9) | 0.0158 (9) | 0.0251 (9) | 0.0003 (7) | 0.0037 (7) | 0.0000 (7) |
C37 | 0.0154 (8) | 0.0164 (8) | 0.0222 (9) | 0.0018 (7) | 0.0005 (7) | −0.0044 (7) |
C38 | 0.0193 (9) | 0.0140 (8) | 0.0193 (9) | 0.0032 (7) | 0.0027 (7) | −0.0017 (7) |
C39 | 0.0159 (8) | 0.0145 (8) | 0.0191 (8) | 0.0001 (6) | −0.0002 (7) | −0.0018 (7) |
C40 | 0.0226 (9) | 0.0148 (8) | 0.0235 (9) | 0.0008 (7) | 0.0016 (7) | −0.0024 (7) |
C41 | 0.0231 (9) | 0.0178 (9) | 0.0317 (10) | 0.0011 (7) | 0.0042 (8) | −0.0058 (8) |
C42 | 0.0243 (9) | 0.0189 (9) | 0.0243 (9) | 0.0027 (7) | 0.0051 (8) | −0.0033 (7) |
C43 | 0.0331 (11) | 0.0252 (11) | 0.0355 (12) | 0.0025 (9) | −0.0068 (9) | −0.0005 (9) |
C44 | 0.0416 (13) | 0.0322 (12) | 0.0356 (12) | −0.0094 (10) | −0.0062 (10) | −0.0090 (10) |
C45 | 0.0498 (14) | 0.0216 (10) | 0.0355 (12) | −0.0041 (9) | 0.0051 (10) | −0.0098 (9) |
C46 | 0.0630 (17) | 0.0199 (11) | 0.0462 (14) | 0.0093 (11) | −0.0120 (12) | −0.0019 (10) |
C47 | 0.0475 (14) | 0.0238 (11) | 0.0349 (12) | 0.0044 (10) | −0.0134 (10) | −0.0047 (9) |
C48 | 0.0279 (10) | 0.0213 (10) | 0.0337 (11) | −0.0058 (8) | 0.0006 (9) | 0.0040 (8) |
C49 | 0.0221 (9) | 0.0121 (8) | 0.0169 (8) | 0.0012 (7) | −0.0020 (7) | −0.0015 (6) |
C50 | 0.0214 (9) | 0.0134 (8) | 0.0174 (8) | 0.0029 (7) | −0.0007 (7) | 0.0003 (7) |
C51 | 0.0197 (9) | 0.0146 (8) | 0.0206 (9) | 0.0002 (7) | −0.0017 (7) | 0.0007 (7) |
C52 | 0.0231 (9) | 0.0153 (8) | 0.0192 (9) | −0.0001 (7) | −0.0025 (7) | −0.0021 (7) |
C53 | 0.0218 (9) | 0.0165 (8) | 0.0181 (9) | 0.0019 (7) | 0.0009 (7) | −0.0006 (7) |
C54 | 0.0198 (9) | 0.0131 (8) | 0.0190 (8) | 0.0010 (7) | −0.0017 (7) | 0.0011 (7) |
C55 | 0.0193 (9) | 0.0147 (8) | 0.0189 (8) | −0.0002 (7) | 0.0005 (7) | −0.0006 (7) |
C56 | 0.0262 (10) | 0.0139 (8) | 0.0222 (9) | −0.0008 (7) | −0.0006 (7) | −0.0003 (7) |
C57 | 0.0312 (10) | 0.0185 (9) | 0.0254 (10) | 0.0009 (8) | −0.0043 (8) | 0.0005 (8) |
C58 | 0.0456 (13) | 0.0209 (10) | 0.0272 (11) | 0.0064 (9) | −0.0121 (9) | 0.0006 (8) |
C59 | 0.100 (2) | 0.0266 (13) | 0.0350 (13) | −0.0102 (14) | 0.0022 (14) | 0.0023 (10) |
C60 | 0.169 (4) | 0.0267 (14) | 0.0451 (17) | −0.014 (2) | −0.021 (2) | 0.0089 (13) |
C61 | 0.142 (4) | 0.0341 (17) | 0.073 (2) | 0.037 (2) | −0.051 (3) | −0.0189 (16) |
C62 | 0.073 (2) | 0.067 (3) | 0.119 (3) | 0.044 (2) | −0.037 (2) | −0.052 (2) |
C63 | 0.0439 (15) | 0.0458 (16) | 0.075 (2) | 0.0129 (12) | −0.0107 (14) | −0.0228 (15) |
C64 | 0.0299 (11) | 0.0262 (10) | 0.0271 (10) | −0.0064 (8) | 0.0056 (8) | −0.0117 (8) |
C65 | 0.072 (2) | 0.0281 (13) | 0.0588 (18) | 0.0036 (13) | −0.0049 (15) | 0.0052 (12) |
C66 | 0.0652 (19) | 0.0569 (18) | 0.0409 (15) | −0.0057 (15) | 0.0089 (13) | −0.0073 (13) |
C67 | 0.0417 (14) | 0.0381 (14) | 0.0630 (17) | 0.0005 (11) | 0.0119 (13) | −0.0096 (12) |
C68 | 0.0584 (17) | 0.0664 (19) | 0.0301 (13) | −0.0032 (14) | −0.0018 (12) | −0.0091 (12) |
C69 | 0.102 (3) | 0.076 (2) | 0.0399 (16) | −0.026 (2) | 0.0234 (17) | −0.0057 (15) |
O1—C3 | 1.377 (2) | C30—C31 | 1.398 (4) |
O1—H1 | 0.8400 | C30—H30 | 0.9500 |
O2—C5 | 1.372 (2) | C31—H31 | 0.9500 |
O2—H2 | 0.8400 | C32—H32A | 0.9800 |
O3—C19 | 1.367 (2) | C32—H32B | 0.9800 |
O3—H3 | 0.8400 | C32—H32C | 0.9800 |
O4—C21 | 1.380 (2) | C33—C38 | 1.390 (3) |
O4—H4 | 0.8400 | C33—C34 | 1.391 (3) |
O5—C35 | 1.385 (2) | C33—H33 | 0.9500 |
O5—H5 | 0.8400 | C34—C35 | 1.395 (3) |
O6—C37 | 1.387 (2) | C35—C36 | 1.396 (3) |
O6—H6 | 0.8400 | C36—C37 | 1.397 (3) |
O7—C51 | 1.387 (2) | C36—C48 | 1.507 (3) |
O7—H7 | 0.8400 | C37—C38 | 1.397 (3) |
O8—C53 | 1.380 (2) | C38—C39 | 1.527 (2) |
O8—H8 | 0.8400 | C39—C50 | 1.524 (2) |
O9—C65 | 1.402 (3) | C39—C40 | 1.543 (2) |
O9—H9 | 0.8400 | C39—H39 | 1.0000 |
O10—C66 | 1.414 (3) | C40—C41 | 1.532 (3) |
O10—H10 | 0.8400 | C40—H40A | 0.9900 |
O11—C67 | 1.416 (3) | C40—H40B | 0.9900 |
O11—H11 | 0.8400 | C41—C42 | 1.510 (3) |
O12—C68 | 1.391 (3) | C41—H41A | 0.9900 |
O12—H12 | 0.8400 | C41—H41B | 0.9900 |
O13—C69 | 1.432 (4) | C42—C43 | 1.381 (3) |
O13—H13 | 0.8400 | C42—C47 | 1.383 (3) |
C1—C2 | 1.387 (3) | C43—C44 | 1.391 (3) |
C1—C6 | 1.392 (3) | C43—H43 | 0.9500 |
C1—H1A | 0.9500 | C44—C45 | 1.376 (4) |
C2—C3 | 1.400 (3) | C44—H44 | 0.9500 |
C2—C55 | 1.525 (2) | C45—C46 | 1.367 (4) |
C3—C4 | 1.398 (3) | C45—H45 | 0.9500 |
C4—C5 | 1.395 (3) | C46—C47 | 1.393 (3) |
C4—C16 | 1.513 (3) | C46—H46 | 0.9500 |
C5—C6 | 1.402 (3) | C47—H47 | 0.9500 |
C6—C7 | 1.531 (3) | C48—H48A | 0.9800 |
C7—C18 | 1.531 (3) | C48—H48B | 0.9800 |
C7—C8 | 1.543 (3) | C48—H48C | 0.9800 |
C7—H7A | 1.0000 | C49—C50 | 1.388 (3) |
C8—C9 | 1.534 (3) | C49—C54 | 1.392 (3) |
C8—H8A | 0.9900 | C49—H49 | 0.9500 |
C8—H8B | 0.9900 | C50—C51 | 1.402 (2) |
C9—C10 | 1.512 (3) | C51—C52 | 1.397 (3) |
C9—H9A | 0.9900 | C52—C53 | 1.400 (3) |
C9—H9B | 0.9900 | C52—C64 | 1.506 (3) |
C10—C11 | 1.377 (3) | C53—C54 | 1.398 (2) |
C10—C15 | 1.381 (3) | C54—C55 | 1.527 (2) |
C11—C12 | 1.391 (4) | C55—C56 | 1.544 (2) |
C11—H11A | 0.9500 | C55—H55 | 1.0000 |
C12—C13 | 1.331 (4) | C56—C57 | 1.529 (3) |
C12—H12A | 0.9500 | C56—H56A | 0.9900 |
C13—C14 | 1.391 (4) | C56—H56B | 0.9900 |
C13—H13A | 0.9500 | C57—C58 | 1.508 (3) |
C14—C15 | 1.387 (4) | C57—H57A | 0.9900 |
C14—H14 | 0.9500 | C57—H57B | 0.9900 |
C15—H15 | 0.9500 | C58—C59 | 1.376 (4) |
C16—H16A | 0.9800 | C58—C63 | 1.390 (4) |
C16—H16B | 0.9800 | C59—C60 | 1.408 (5) |
C16—H16C | 0.9800 | C59—H59 | 0.9500 |
C17—C18 | 1.390 (3) | C60—C61 | 1.352 (6) |
C17—C22 | 1.391 (3) | C60—H60 | 0.9500 |
C17—H17 | 0.9500 | C61—C62 | 1.358 (7) |
C18—C19 | 1.408 (3) | C61—H61 | 0.9500 |
C19—C20 | 1.402 (3) | C62—C63 | 1.399 (4) |
C20—C21 | 1.401 (3) | C62—H62 | 0.9500 |
C20—C32 | 1.505 (3) | C63—H63 | 0.9500 |
C21—C22 | 1.399 (3) | C64—H64A | 0.9800 |
C22—C23 | 1.527 (3) | C64—H64B | 0.9800 |
C23—C34 | 1.524 (3) | C64—H64C | 0.9800 |
C23—C24 | 1.538 (3) | C65—H65A | 0.9800 |
C23—H23 | 1.0000 | C65—H65B | 0.9800 |
C24—C25 | 1.534 (3) | C65—H65C | 0.9800 |
C24—H24A | 0.9900 | C66—H66A | 0.9800 |
C24—H24B | 0.9900 | C66—H66B | 0.9800 |
C25—C26 | 1.509 (3) | C66—H66C | 0.9800 |
C25—H25A | 0.9900 | C67—H67A | 0.9800 |
C25—H25B | 0.9900 | C67—H67B | 0.9800 |
C26—C31 | 1.380 (3) | C67—H67C | 0.9800 |
C26—C27 | 1.390 (3) | C68—H68A | 0.9800 |
C27—C28 | 1.389 (3) | C68—H68B | 0.9800 |
C27—H27 | 0.9500 | C68—H68C | 0.9800 |
C28—C29 | 1.372 (4) | C69—H69A | 0.9800 |
C28—H28 | 0.9500 | C69—H69B | 0.9800 |
C29—C30 | 1.386 (4) | C69—H69C | 0.9800 |
C29—H29 | 0.9500 | ||
C3—O1—H1 | 109.5 | C35—C36—C37 | 117.46 (17) |
C5—O2—H2 | 109.5 | C35—C36—C48 | 122.06 (17) |
C19—O3—H3 | 109.5 | C37—C36—C48 | 120.48 (17) |
C21—O4—H4 | 109.5 | O6—C37—C36 | 116.36 (16) |
C35—O5—H5 | 109.5 | O6—C37—C38 | 121.06 (16) |
C37—O6—H6 | 109.5 | C36—C37—C38 | 122.58 (17) |
C51—O7—H7 | 109.5 | C33—C38—C37 | 117.24 (17) |
C53—O8—H8 | 109.5 | C33—C38—C39 | 121.07 (16) |
C65—O9—H9 | 109.5 | C37—C38—C39 | 121.61 (16) |
C66—O10—H10 | 109.5 | C50—C39—C38 | 112.18 (14) |
C67—O11—H11 | 109.5 | C50—C39—C40 | 111.99 (15) |
C68—O12—H12 | 109.5 | C38—C39—C40 | 111.45 (15) |
C69—O13—H13 | 109.5 | C50—C39—H39 | 106.9 |
C2—C1—C6 | 122.80 (17) | C38—C39—H39 | 106.9 |
C2—C1—H1A | 118.6 | C40—C39—H39 | 106.9 |
C6—C1—H1A | 118.6 | C41—C40—C39 | 113.01 (15) |
C1—C2—C3 | 117.60 (17) | C41—C40—H40A | 109.0 |
C1—C2—C55 | 121.22 (16) | C39—C40—H40A | 109.0 |
C3—C2—C55 | 121.18 (16) | C41—C40—H40B | 109.0 |
O1—C3—C4 | 117.27 (16) | C39—C40—H40B | 109.0 |
O1—C3—C2 | 120.51 (17) | H40A—C40—H40B | 107.8 |
C4—C3—C2 | 122.21 (17) | C42—C41—C40 | 111.48 (16) |
C5—C4—C3 | 117.59 (17) | C42—C41—H41A | 109.3 |
C5—C4—C16 | 122.23 (17) | C40—C41—H41A | 109.3 |
C3—C4—C16 | 120.18 (17) | C42—C41—H41B | 109.3 |
O2—C5—C4 | 121.68 (17) | C40—C41—H41B | 109.3 |
O2—C5—C6 | 116.01 (17) | H41A—C41—H41B | 108.0 |
C4—C5—C6 | 122.27 (17) | C43—C42—C47 | 117.87 (19) |
C1—C6—C5 | 117.41 (17) | C43—C42—C41 | 120.73 (18) |
C1—C6—C7 | 121.48 (16) | C47—C42—C41 | 121.39 (19) |
C5—C6—C7 | 121.10 (16) | C42—C43—C44 | 121.3 (2) |
C6—C7—C18 | 110.57 (15) | C42—C43—H43 | 119.3 |
C6—C7—C8 | 112.33 (15) | C44—C43—H43 | 119.3 |
C18—C7—C8 | 111.52 (15) | C45—C44—C43 | 119.9 (2) |
C6—C7—H7A | 107.4 | C45—C44—H44 | 120.0 |
C18—C7—H7A | 107.4 | C43—C44—H44 | 120.0 |
C8—C7—H7A | 107.4 | C46—C45—C44 | 119.5 (2) |
C9—C8—C7 | 114.41 (16) | C46—C45—H45 | 120.2 |
C9—C8—H8A | 108.7 | C44—C45—H45 | 120.2 |
C7—C8—H8A | 108.7 | C45—C46—C47 | 120.5 (2) |
C9—C8—H8B | 108.7 | C45—C46—H46 | 119.8 |
C7—C8—H8B | 108.7 | C47—C46—H46 | 119.8 |
H8A—C8—H8B | 107.6 | C42—C47—C46 | 120.9 (2) |
C10—C9—C8 | 112.78 (17) | C42—C47—H47 | 119.6 |
C10—C9—H9A | 109.0 | C46—C47—H47 | 119.6 |
C8—C9—H9A | 109.0 | C36—C48—H48A | 109.5 |
C10—C9—H9B | 109.0 | C36—C48—H48B | 109.5 |
C8—C9—H9B | 109.0 | H48A—C48—H48B | 109.5 |
H9A—C9—H9B | 107.8 | C36—C48—H48C | 109.5 |
C11—C10—C15 | 116.1 (2) | H48A—C48—H48C | 109.5 |
C11—C10—C9 | 122.9 (2) | H48B—C48—H48C | 109.5 |
C15—C10—C9 | 121.0 (2) | C50—C49—C54 | 122.98 (16) |
C10—C11—C12 | 121.8 (2) | C50—C49—H49 | 118.5 |
C10—C11—H11A | 119.1 | C54—C49—H49 | 118.5 |
C12—C11—H11A | 119.1 | C49—C50—C51 | 117.38 (16) |
C13—C12—C11 | 121.3 (3) | C49—C50—C39 | 121.37 (16) |
C13—C12—H12A | 119.4 | C51—C50—C39 | 121.24 (16) |
C11—C12—H12A | 119.4 | O7—C51—C52 | 120.82 (16) |
C12—C13—C14 | 119.1 (3) | O7—C51—C50 | 116.92 (16) |
C12—C13—H13A | 120.5 | C52—C51—C50 | 122.24 (17) |
C14—C13—H13A | 120.5 | C51—C52—C53 | 117.72 (16) |
C15—C14—C13 | 119.4 (3) | C51—C52—C64 | 121.34 (17) |
C15—C14—H14 | 120.3 | C53—C52—C64 | 120.94 (17) |
C13—C14—H14 | 120.3 | O8—C53—C54 | 117.25 (16) |
C10—C15—C14 | 122.3 (3) | O8—C53—C52 | 120.69 (16) |
C10—C15—H15 | 118.9 | C54—C53—C52 | 122.06 (17) |
C14—C15—H15 | 118.9 | C49—C54—C53 | 117.58 (17) |
C4—C16—H16A | 109.5 | C49—C54—C55 | 121.91 (16) |
C4—C16—H16B | 109.5 | C53—C54—C55 | 120.49 (16) |
H16A—C16—H16B | 109.5 | C2—C55—C54 | 110.54 (14) |
C4—C16—H16C | 109.5 | C2—C55—C56 | 112.50 (15) |
H16A—C16—H16C | 109.5 | C54—C55—C56 | 112.60 (15) |
H16B—C16—H16C | 109.5 | C2—C55—H55 | 106.9 |
C18—C17—C22 | 124.03 (17) | C54—C55—H55 | 106.9 |
C18—C17—H17 | 118.0 | C56—C55—H55 | 106.9 |
C22—C17—H17 | 118.0 | C57—C56—C55 | 110.91 (15) |
C17—C18—C19 | 116.81 (17) | C57—C56—H56A | 109.5 |
C17—C18—C7 | 120.96 (16) | C55—C56—H56A | 109.5 |
C19—C18—C7 | 122.23 (17) | C57—C56—H56B | 109.5 |
O3—C19—C20 | 115.56 (17) | C55—C56—H56B | 109.5 |
O3—C19—C18 | 123.02 (18) | H56A—C56—H56B | 108.0 |
C20—C19—C18 | 121.42 (17) | C58—C57—C56 | 114.43 (16) |
C21—C20—C19 | 119.04 (17) | C58—C57—H57A | 108.7 |
C21—C20—C32 | 121.71 (18) | C56—C57—H57A | 108.7 |
C19—C20—C32 | 119.23 (18) | C58—C57—H57B | 108.7 |
O4—C21—C22 | 122.31 (17) | C56—C57—H57B | 108.7 |
O4—C21—C20 | 116.51 (17) | H57A—C57—H57B | 107.6 |
C22—C21—C20 | 121.17 (17) | C59—C58—C63 | 118.5 (2) |
C17—C22—C21 | 117.49 (17) | C59—C58—C57 | 122.0 (2) |
C17—C22—C23 | 121.12 (16) | C63—C58—C57 | 119.5 (2) |
C21—C22—C23 | 121.39 (17) | C58—C59—C60 | 120.0 (3) |
C34—C23—C22 | 110.60 (14) | C58—C59—H59 | 120.0 |
C34—C23—C24 | 111.60 (15) | C60—C59—H59 | 120.0 |
C22—C23—C24 | 113.00 (15) | C61—C60—C59 | 120.7 (4) |
C34—C23—H23 | 107.1 | C61—C60—H60 | 119.6 |
C22—C23—H23 | 107.1 | C59—C60—H60 | 119.6 |
C24—C23—H23 | 107.1 | C60—C61—C62 | 120.0 (3) |
C25—C24—C23 | 113.39 (16) | C60—C61—H61 | 120.0 |
C25—C24—H24A | 108.9 | C62—C61—H61 | 120.0 |
C23—C24—H24A | 108.9 | C61—C62—C63 | 120.4 (4) |
C25—C24—H24B | 108.9 | C61—C62—H62 | 119.8 |
C23—C24—H24B | 108.9 | C63—C62—H62 | 119.8 |
H24A—C24—H24B | 107.7 | C58—C63—C62 | 120.3 (4) |
C26—C25—C24 | 111.64 (17) | C58—C63—H63 | 119.9 |
C26—C25—H25A | 109.3 | C62—C63—H63 | 119.9 |
C24—C25—H25A | 109.3 | C52—C64—H64A | 109.5 |
C26—C25—H25B | 109.3 | C52—C64—H64B | 109.5 |
C24—C25—H25B | 109.3 | H64A—C64—H64B | 109.5 |
H25A—C25—H25B | 108.0 | C52—C64—H64C | 109.5 |
C31—C26—C27 | 118.4 (2) | H64A—C64—H64C | 109.5 |
C31—C26—C25 | 121.0 (2) | H64B—C64—H64C | 109.5 |
C27—C26—C25 | 120.6 (2) | O9—C65—H65A | 109.5 |
C28—C27—C26 | 120.9 (2) | O9—C65—H65B | 109.5 |
C28—C27—H27 | 119.6 | H65A—C65—H65B | 109.5 |
C26—C27—H27 | 119.6 | O9—C65—H65C | 109.5 |
C29—C28—C27 | 120.0 (2) | H65A—C65—H65C | 109.5 |
C29—C28—H28 | 120.0 | H65B—C65—H65C | 109.5 |
C27—C28—H28 | 120.0 | O10—C66—H66A | 109.5 |
C28—C29—C30 | 120.3 (2) | O10—C66—H66B | 109.5 |
C28—C29—H29 | 119.9 | H66A—C66—H66B | 109.5 |
C30—C29—H29 | 119.9 | O10—C66—H66C | 109.5 |
C29—C30—C31 | 119.3 (3) | H66A—C66—H66C | 109.5 |
C29—C30—H30 | 120.4 | H66B—C66—H66C | 109.5 |
C31—C30—H30 | 120.4 | O11—C67—H67A | 109.5 |
C26—C31—C30 | 121.1 (2) | O11—C67—H67B | 109.5 |
C26—C31—H31 | 119.4 | H67A—C67—H67B | 109.5 |
C30—C31—H31 | 119.4 | O11—C67—H67C | 109.5 |
C20—C32—H32A | 109.5 | H67A—C67—H67C | 109.5 |
C20—C32—H32B | 109.5 | H67B—C67—H67C | 109.5 |
H32A—C32—H32B | 109.5 | O12—C68—H68A | 109.5 |
C20—C32—H32C | 109.5 | O12—C68—H68B | 109.5 |
H32A—C32—H32C | 109.5 | H68A—C68—H68B | 109.5 |
H32B—C32—H32C | 109.5 | O12—C68—H68C | 109.5 |
C38—C33—C34 | 122.69 (17) | H68A—C68—H68C | 109.5 |
C38—C33—H33 | 118.7 | H68B—C68—H68C | 109.5 |
C34—C33—H33 | 118.7 | O13—C69—H69A | 109.5 |
C33—C34—C35 | 117.81 (17) | O13—C69—H69B | 109.5 |
C33—C34—C23 | 120.98 (16) | H69A—C69—H69B | 109.5 |
C35—C34—C23 | 121.20 (16) | O13—C69—H69C | 109.5 |
O5—C35—C34 | 117.01 (17) | H69A—C69—H69C | 109.5 |
O5—C35—C36 | 120.79 (17) | H69B—C69—H69C | 109.5 |
C34—C35—C36 | 122.12 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O8 | 0.84 | 1.87 | 2.709 (2) | 178 |
O2—H2···O6i | 0.84 | 1.85 | 2.6442 (19) | 157 |
O3—H3···O2 | 0.84 | 1.85 | 2.687 (2) | 171 |
O4—H4···O5 | 0.84 | 1.98 | 2.805 (2) | 169 |
O5—H5···O10 | 0.84 | 1.82 | 2.643 (2) | 165 |
O6—H6···O7 | 0.84 | 1.86 | 2.7001 (19) | 177 |
O7—H7···O9ii | 0.84 | 1.86 | 2.639 (2) | 154 |
O8—H8···O12 | 0.84 | 1.90 | 2.631 (2) | 145 |
O10—H10···O13ii | 0.84 | 1.92 | 2.754 (3) | 173 |
O11—H11···O1 | 0.84 | 1.93 | 2.716 (2) | 156 |
O12—H12···O13 | 0.84 | 1.91 | 2.748 (3) | 174 |
O13—H13···O11 | 0.84 | 1.84 | 2.671 (3) | 172 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C64H64O8·5CH4O·0.103H2O |
Mr | 1123.22 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 105 |
a, b, c (Å) | 12.3109 (3), 30.6151 (7), 16.5024 (3) |
β (°) | 92.8385 (19) |
V (Å3) | 6212.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.65 × 0.50 × 0.50 |
Data collection | |
Diffractometer | Oxford Xcalibur-2 area-detector |
Absorption correction | Multi-scan [empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm of CrysAlis RED (Oxford Diffraction, 2006)] |
Tmin, Tmax | 0.785, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 74273, 14218, 10324 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.175, 1.09 |
No. of reflections | 14218 |
No. of parameters | 765 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.39 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O8 | 0.84 | 1.87 | 2.709 (2) | 177.8 |
O2—H2···O6i | 0.84 | 1.85 | 2.6442 (19) | 156.5 |
O3—H3···O2 | 0.84 | 1.85 | 2.687 (2) | 170.8 |
O4—H4···O5 | 0.84 | 1.98 | 2.805 (2) | 169.3 |
O5—H5···O10 | 0.84 | 1.82 | 2.643 (2) | 165.0 |
O6—H6···O7 | 0.84 | 1.86 | 2.7001 (19) | 177.2 |
O7—H7···O9ii | 0.84 | 1.86 | 2.639 (2) | 154.1 |
O8—H8···O12 | 0.84 | 1.90 | 2.631 (2) | 144.6 |
O10—H10···O13ii | 0.84 | 1.92 | 2.754 (3) | 173.4 |
O11—H11···O1 | 0.84 | 1.93 | 2.716 (2) | 156.1 |
O12—H12···O13 | 0.84 | 1.91 | 2.748 (3) | 174.0 |
O13—H13···O11 | 0.84 | 1.84 | 2.671 (3) | 172.2 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1. |
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In the title compound, (I), the [4]arene moiety, (I A), is a cyclic tetramer. The labelling scheme for one of the monomers, shown in Fig.1, extends over the whole molecule such that for monomer n the numbers p and q associated with particular C and O atoms, respectively, become p' = p + 16 x (n - 1) and q' = q + 2 x (n - 1). The asymmetric unit of (I) is shown in Fig. 2. The bond lengths and bond angles all fall within the normal ranges and are not discussed further. In molecule (I A) the 2-phenylethyl 'feet' all lie to one side of the macrocyclic ring surrounding the site of the partially occupied water molecule, O1W, with their phenyl groups in a cyclic edge-to-face arrangement. All but one of the OH groups participate in O—H···O hydrogen-bond formation (Table 1) and all but three of those listed occur within the asymmetric unit (Fig.2). The acceptor for methanolic O9 is the benzene ring, with centroid Cg, defined by C17—C22. The parameters for this O—H..π contact include the H..Cg distance and O—H..Cg angle of 2.48 Å and 173°, respectively. The O2—H2.·O6i (symmetry code as in Table 1) hydrogen-bond provides direct connection between molecules (1 A) in the propagation of chains in the direction of the cell edge a. The hydrogen-bonds O7—H7.·O9ii and O10—H10.·O13ii link chains, related to one another by crystallographic centres of symmetry, in pairs as shown in Fig. 3.
The partial occupancy of the water molecule associated with (I) is not exclusive to this structure, and has been noted before in related structures. For related literature, see Tunstad et al. (1989) and Cram et al. (1988).