Cocrystallization and configurations of myo-inositol-1,2-L-camphor acetals in two crystal structures
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107004416/gz3065sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107004416/gz3065Asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107004416/gz3065Bsup3.hkl |
CCDC references: 641805; 641806
For related literature, see: Allen (2002); Baars & Hoberg (2006); Chung et al. (1994); Clegg et al. (1995); Cousins et al. (2004); Cremer & Pople (1975); Desiraju & Steiner (1999); Dillen et al. (2000); Evans & Boeyens (1989); Flack (1983); Flack & Bernardinelli (2000); Lindberg et al. (2002); Mikolajczyk et al. (1996); Pietrusiewicz et al. (1992); SCM (2006); Sheldrick (1997); Spiers et al. (1996, 1997); Steiner et al. (1993); Vosko et al. (1980).
All the L-camphor atoms in (II) and (III) (C7, C8–C16 and their H atoms) were freely refined in two sets, each with one common occupancy factor restrained so that the sum of the two was unity. The final occupancies were 0.685 (2)/0.315 (2). The final difference maps showed no significant discrepancies, justifying this choice of disorder modelling. The four C7,C7'—O1,O2 distances were restrained to a common dimension (with an su of 0.01, using the SHEXL97 SADI option; Sheldrick, 1997).
All H atoms bound to carbon were constrained to their expected geometries (C—H = 0.98–1.00 Å). H atoms on inositol O atoms were restrained to tetrahedral positions with O—H distances of 0.84 (s.u.?) Å (AFIX 87). Positions of water H atoms were restrained to O—H distances of 0.84 Å (DFIX). All methyl, tertiary and hydroxyl H atoms were refined with Uiso(H) values of, respectively, 1.5, 1.2 and 1.5 times Ueq of the parent atom. In the absence of significant anomalous scattering, the values of the Flack (1983) parameter were indeterminate (Flack & Bernardinelli, 2000).
For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C16H26O6 | F(000) = 680 |
Mr = 314.37 | Dx = 1.341 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 2866 reflections |
a = 12.700 (3) Å | θ = 2.3–24.2° |
b = 6.9721 (17) Å | µ = 0.10 mm−1 |
c = 18.422 (5) Å | T = 169 K |
β = 107.275 (3)° | Hexagonal, colourless |
V = 1557.7 (7) Å3 | 0.47 × 0.33 × 0.03 mm |
Z = 4 |
Bruker-Nonius APEX2 CCD area-detector diffractometer | 2953 independent reflections |
Radiation source: fine-focus sealed tube | 2026 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.5°, θmin = 2.3° |
ϕ and ω scans | h = −11→15 |
Absorption correction: multi-scan (Blessing, 1995) | k = −8→8 |
Tmin = 0.796, Tmax = 0.997 | l = −22→22 |
8809 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0452P)2 + 0.8396P] where P = (Fo2 + 2Fc2)/3 |
2953 reflections | (Δ/σ)max = 0.009 |
206 parameters | Δρmax = 0.27 e Å−3 |
1 restraint | Δρmin = −0.26 e Å−3 |
C16H26O6 | V = 1557.7 (7) Å3 |
Mr = 314.37 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 12.700 (3) Å | µ = 0.10 mm−1 |
b = 6.9721 (17) Å | T = 169 K |
c = 18.422 (5) Å | 0.47 × 0.33 × 0.03 mm |
β = 107.275 (3)° |
Bruker-Nonius APEX2 CCD area-detector diffractometer | 2953 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 2026 reflections with I > 2σ(I) |
Tmin = 0.796, Tmax = 0.997 | Rint = 0.055 |
8809 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 1 restraint |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.27 e Å−3 |
2953 reflections | Δρmin = −0.26 e Å−3 |
206 parameters |
Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 0.8 mm diameter collimator was used. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.34056 (17) | 0.3160 (3) | 0.23347 (11) | 0.0229 (5) | |
O2 | 0.19305 (17) | 0.5175 (4) | 0.18530 (11) | 0.0237 (6) | |
O3 | 0.2618 (2) | 0.7930 (3) | 0.08317 (17) | 0.0461 (8) | |
H3O | 0.2995 | 0.8923 | 0.0980 | 0.069* | |
O4 | 0.4747 (2) | 0.7149 (4) | 0.06925 (15) | 0.0388 (7) | |
H4O | 0.4670 | 0.8072 | 0.0965 | 0.058* | |
O5 | 0.54279 (19) | 0.3208 (4) | 0.07593 (12) | 0.0300 (6) | |
H5O | 0.6078 | 0.3453 | 0.1020 | 0.045* | |
O6 | 0.44603 (19) | 0.0562 (3) | 0.15623 (13) | 0.0295 (6) | |
H6O | 0.5100 | 0.0528 | 0.1520 | 0.044* | |
C1 | 0.2974 (3) | 0.2772 (5) | 0.15264 (17) | 0.0208 (8) | |
H1 | 0.2414 | 0.1721 | 0.1435 | 0.025* | |
C2 | 0.2408 (3) | 0.4688 (5) | 0.12480 (18) | 0.0215 (8) | |
H2 | 0.1820 | 0.4527 | 0.0752 | 0.026* | |
C3 | 0.3228 (3) | 0.6276 (5) | 0.11944 (19) | 0.0269 (9) | |
H3 | 0.3675 | 0.6640 | 0.1721 | 0.032* | |
C4 | 0.4016 (3) | 0.5614 (5) | 0.0750 (2) | 0.0257 (9) | |
H4 | 0.3571 | 0.5223 | 0.0226 | 0.031* | |
C5 | 0.4670 (3) | 0.3877 (5) | 0.11557 (19) | 0.0247 (8) | |
H5 | 0.5092 | 0.4242 | 0.1687 | 0.030* | |
C6 | 0.3889 (3) | 0.2242 (5) | 0.11751 (18) | 0.0198 (8) | |
H6 | 0.3520 | 0.1861 | 0.0636 | 0.024* | |
C7 | 0.2503 (3) | 0.4057 (5) | 0.25293 (17) | 0.0211 (8) | |
C8 | 0.2928 (3) | 0.5323 (5) | 0.32573 (17) | 0.0243 (8) | |
C9 | 0.1908 (3) | 0.6561 (5) | 0.32850 (19) | 0.0262 (8) | |
H9A | 0.2132 | 0.7581 | 0.3674 | 0.031* | |
H9B | 0.1551 | 0.7160 | 0.2785 | 0.031* | |
C10 | 0.1116 (3) | 0.5099 (6) | 0.3496 (2) | 0.0311 (9) | |
H10A | 0.0987 | 0.5442 | 0.3984 | 0.037* | |
H10B | 0.0399 | 0.5033 | 0.3094 | 0.037* | |
C11 | 0.1755 (3) | 0.3176 (6) | 0.35615 (17) | 0.0245 (8) | |
H11 | 0.1508 | 0.2160 | 0.3858 | 0.029* | |
C12 | 0.1712 (3) | 0.2572 (5) | 0.27395 (17) | 0.0235 (9) | |
H12A | 0.0954 | 0.2672 | 0.2389 | 0.028* | |
H12B | 0.1982 | 0.1243 | 0.2728 | 0.028* | |
C13 | 0.3966 (3) | 0.6486 (6) | 0.3315 (2) | 0.0341 (10) | |
H13A | 0.4553 | 0.5626 | 0.3269 | 0.051* | |
H13B | 0.4202 | 0.7141 | 0.3808 | 0.051* | |
H13C | 0.3809 | 0.7438 | 0.2906 | 0.051* | |
C14 | 0.2977 (3) | 0.3814 (5) | 0.39083 (17) | 0.0231 (8) | |
C15 | 0.3820 (3) | 0.2177 (5) | 0.39846 (18) | 0.0282 (9) | |
H15A | 0.4564 | 0.2717 | 0.4100 | 0.042* | |
H15B | 0.3649 | 0.1460 | 0.3506 | 0.042* | |
H15C | 0.3782 | 0.1313 | 0.4396 | 0.042* | |
C16 | 0.3210 (3) | 0.4756 (6) | 0.47065 (18) | 0.0316 (9) | |
H16A | 0.3142 | 0.3788 | 0.5075 | 0.047* | |
H16B | 0.2677 | 0.5788 | 0.4683 | 0.047* | |
H16C | 0.3959 | 0.5286 | 0.4863 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0165 (12) | 0.0351 (14) | 0.0170 (11) | 0.0003 (12) | 0.0050 (9) | −0.0001 (11) |
O2 | 0.0170 (13) | 0.0387 (14) | 0.0178 (12) | 0.0029 (12) | 0.0087 (10) | 0.0028 (11) |
O3 | 0.0566 (18) | 0.0216 (15) | 0.078 (2) | 0.0085 (15) | 0.0469 (16) | 0.0085 (16) |
O4 | 0.0503 (17) | 0.0269 (15) | 0.0533 (19) | −0.0105 (14) | 0.0370 (15) | −0.0104 (13) |
O5 | 0.0118 (12) | 0.0505 (16) | 0.0291 (13) | 0.0041 (14) | 0.0082 (10) | 0.0096 (13) |
O6 | 0.0219 (14) | 0.0330 (15) | 0.0316 (14) | 0.0029 (13) | 0.0050 (12) | 0.0075 (12) |
C1 | 0.0173 (18) | 0.030 (2) | 0.0147 (17) | −0.0046 (17) | 0.0048 (14) | 0.0011 (15) |
C2 | 0.021 (2) | 0.027 (2) | 0.0182 (17) | 0.0049 (17) | 0.0090 (15) | 0.0003 (15) |
C3 | 0.034 (2) | 0.028 (2) | 0.025 (2) | 0.0021 (19) | 0.0175 (17) | 0.0031 (16) |
C4 | 0.032 (2) | 0.024 (2) | 0.0259 (18) | −0.0060 (18) | 0.0156 (16) | −0.0006 (17) |
C5 | 0.022 (2) | 0.033 (2) | 0.0199 (18) | −0.0008 (17) | 0.0083 (15) | −0.0015 (16) |
C6 | 0.0153 (18) | 0.0243 (19) | 0.0196 (18) | 0.0023 (17) | 0.0049 (14) | 0.0035 (15) |
C7 | 0.0150 (18) | 0.0302 (19) | 0.0180 (17) | 0.0057 (16) | 0.0045 (14) | 0.0053 (15) |
C8 | 0.021 (2) | 0.032 (2) | 0.0205 (17) | −0.0065 (18) | 0.0076 (15) | −0.0026 (17) |
C9 | 0.024 (2) | 0.035 (2) | 0.0201 (18) | 0.0011 (19) | 0.0064 (15) | −0.0008 (17) |
C10 | 0.021 (2) | 0.050 (2) | 0.0225 (18) | 0.004 (2) | 0.0073 (15) | 0.0023 (18) |
C11 | 0.0182 (18) | 0.038 (2) | 0.0205 (17) | −0.0042 (19) | 0.0105 (14) | 0.0015 (17) |
C12 | 0.0199 (19) | 0.029 (2) | 0.0199 (18) | −0.0019 (17) | 0.0031 (15) | 0.0032 (15) |
C13 | 0.031 (2) | 0.045 (2) | 0.029 (2) | −0.014 (2) | 0.0129 (17) | −0.0080 (19) |
C14 | 0.0114 (18) | 0.039 (2) | 0.0183 (17) | −0.0019 (17) | 0.0031 (14) | −0.0010 (15) |
C15 | 0.021 (2) | 0.042 (2) | 0.0212 (19) | 0.0016 (19) | 0.0068 (15) | 0.0024 (17) |
C16 | 0.024 (2) | 0.048 (3) | 0.0245 (19) | −0.002 (2) | 0.0084 (16) | −0.0013 (17) |
O1—C7 | 1.441 (4) | C8—C13 | 1.524 (5) |
O1—C1 | 1.451 (4) | C8—C9 | 1.570 (5) |
O2—C2 | 1.458 (4) | C8—C14 | 1.582 (5) |
O2—C7 | 1.466 (4) | C9—C10 | 1.560 (5) |
O3—C3 | 1.438 (4) | C9—H9A | 0.9900 |
O3—H3O | 0.8400 | C9—H9B | 0.9900 |
O4—C4 | 1.441 (4) | C10—C11 | 1.553 (5) |
O4—H4O | 0.8400 | C10—H10A | 0.9900 |
O5—C5 | 1.447 (4) | C10—H10B | 0.9900 |
O5—H5O | 0.8400 | C11—C12 | 1.557 (4) |
O6—C6 | 1.449 (4) | C11—C14 | 1.558 (5) |
O6—H6O | 0.8400 | C11—H11 | 1.0000 |
C1—C2 | 1.531 (5) | C12—H12A | 0.9900 |
C1—C6 | 1.534 (4) | C12—H12B | 0.9900 |
C1—H1 | 1.0000 | C13—H13A | 0.9800 |
C2—C3 | 1.543 (5) | C13—H13B | 0.9800 |
C2—H2 | 1.0000 | C13—H13C | 0.9800 |
C3—C4 | 1.541 (5) | C14—C15 | 1.542 (5) |
C3—H3 | 1.0000 | C14—C16 | 1.557 (4) |
C4—C5 | 1.532 (5) | C15—H15A | 0.9800 |
C4—H4 | 1.0000 | C15—H15B | 0.9800 |
C5—C6 | 1.518 (5) | C15—H15C | 0.9800 |
C5—H5 | 1.0000 | C16—H16A | 0.9800 |
C6—H6 | 1.0000 | C16—H16B | 0.9800 |
C7—C8 | 1.562 (5) | C16—H16C | 0.9800 |
C7—C12 | 1.569 (4) | ||
C7—O1—C1 | 104.5 (2) | C13—C8—C14 | 117.5 (3) |
C2—O2—C7 | 108.2 (2) | C7—C8—C14 | 101.6 (3) |
C3—O3—H3O | 109.5 | C9—C8—C14 | 100.9 (3) |
C4—O4—H4O | 109.5 | C10—C9—C8 | 104.4 (3) |
C5—O5—H5O | 109.5 | C10—C9—H9A | 110.9 |
C6—O6—H6O | 109.5 | C8—C9—H9A | 110.9 |
O1—C1—C2 | 100.2 (2) | C10—C9—H9B | 110.9 |
O1—C1—C6 | 112.0 (2) | C8—C9—H9B | 110.9 |
C2—C1—C6 | 114.1 (3) | H9A—C9—H9B | 108.9 |
O1—C1—H1 | 110.0 | C11—C10—C9 | 102.9 (3) |
C2—C1—H1 | 110.0 | C11—C10—H10A | 111.2 |
C6—C1—H1 | 110.0 | C9—C10—H10A | 111.2 |
O2—C2—C1 | 102.0 (2) | C11—C10—H10B | 111.2 |
O2—C2—C3 | 108.9 (3) | C9—C10—H10B | 111.2 |
C1—C2—C3 | 112.9 (3) | H10A—C10—H10B | 109.1 |
O2—C2—H2 | 110.9 | C10—C11—C12 | 107.0 (3) |
C1—C2—H2 | 110.9 | C10—C11—C14 | 102.7 (3) |
C3—C2—H2 | 110.9 | C12—C11—C14 | 102.6 (2) |
O3—C3—C4 | 109.8 (3) | C10—C11—H11 | 114.4 |
O3—C3—C2 | 109.0 (3) | C12—C11—H11 | 114.4 |
C4—C3—C2 | 112.1 (3) | C14—C11—H11 | 114.4 |
O3—C3—H3 | 108.6 | C11—C12—C7 | 102.8 (2) |
C4—C3—H3 | 108.6 | C11—C12—H12A | 111.2 |
C2—C3—H3 | 108.6 | C7—C12—H12A | 111.2 |
O4—C4—C5 | 110.8 (3) | C11—C12—H12B | 111.2 |
O4—C4—C3 | 110.5 (3) | C7—C12—H12B | 111.2 |
C5—C4—C3 | 108.7 (3) | H12A—C12—H12B | 109.1 |
O4—C4—H4 | 108.9 | C8—C13—H13A | 109.5 |
C5—C4—H4 | 108.9 | C8—C13—H13B | 109.5 |
C3—C4—H4 | 108.9 | H13A—C13—H13B | 109.5 |
O5—C5—C6 | 107.9 (3) | C8—C13—H13C | 109.5 |
O5—C5—C4 | 110.7 (3) | H13A—C13—H13C | 109.5 |
C6—C5—C4 | 110.0 (3) | H13B—C13—H13C | 109.5 |
O5—C5—H5 | 109.4 | C15—C14—C16 | 107.1 (3) |
C6—C5—H5 | 109.4 | C15—C14—C11 | 114.0 (3) |
C4—C5—H5 | 109.4 | C16—C14—C11 | 113.2 (3) |
O6—C6—C5 | 112.6 (3) | C15—C14—C8 | 115.6 (3) |
O6—C6—C1 | 108.6 (2) | C16—C14—C8 | 112.9 (3) |
C5—C6—C1 | 114.3 (3) | C11—C14—C8 | 93.9 (2) |
O6—C6—H6 | 107.0 | C14—C15—H15A | 109.5 |
C5—C6—H6 | 107.0 | C14—C15—H15B | 109.5 |
C1—C6—H6 | 107.0 | H15A—C15—H15B | 109.5 |
O1—C7—O2 | 104.4 (2) | C14—C15—H15C | 109.5 |
O1—C7—C8 | 111.2 (3) | H15A—C15—H15C | 109.5 |
O2—C7—C8 | 112.8 (3) | H15B—C15—H15C | 109.5 |
O1—C7—C12 | 113.0 (3) | C14—C16—H16A | 109.5 |
O2—C7—C12 | 111.6 (3) | C14—C16—H16B | 109.5 |
C8—C7—C12 | 104.1 (2) | H16A—C16—H16B | 109.5 |
C13—C8—C7 | 115.6 (3) | C14—C16—H16C | 109.5 |
C13—C8—C9 | 114.2 (3) | H16A—C16—H16C | 109.5 |
C7—C8—C9 | 105.1 (3) | H16B—C16—H16C | 109.5 |
C7—O1—C1—C2 | 45.5 (3) | O2—C7—C8—C13 | −76.8 (4) |
C7—O1—C1—C6 | 166.8 (3) | C12—C7—C8—C13 | 162.0 (3) |
C7—O2—C2—C1 | 19.2 (3) | O1—C7—C8—C9 | 167.0 (3) |
C7—O2—C2—C3 | −100.3 (3) | O2—C7—C8—C9 | 50.1 (3) |
O1—C1—C2—O2 | −39.0 (3) | C12—C7—C8—C9 | −71.1 (3) |
C6—C1—C2—O2 | −158.9 (3) | O1—C7—C8—C14 | −88.3 (3) |
O1—C1—C2—C3 | 77.7 (3) | O2—C7—C8—C14 | 154.8 (2) |
C6—C1—C2—C3 | −42.2 (4) | C12—C7—C8—C14 | 33.7 (3) |
O2—C2—C3—O3 | −75.4 (3) | C13—C8—C9—C10 | −161.2 (3) |
C1—C2—C3—O3 | 172.1 (3) | C7—C8—C9—C10 | 71.0 (3) |
O2—C2—C3—C4 | 162.9 (3) | C14—C8—C9—C10 | −34.3 (3) |
C1—C2—C3—C4 | 50.4 (4) | C8—C9—C10—C11 | −0.4 (3) |
O3—C3—C4—O4 | 57.1 (4) | C9—C10—C11—C12 | −71.8 (3) |
C2—C3—C4—O4 | 178.4 (3) | C9—C10—C11—C14 | 35.8 (3) |
O3—C3—C4—C5 | 178.9 (3) | C10—C11—C12—C7 | 71.5 (3) |
C2—C3—C4—C5 | −59.8 (4) | C14—C11—C12—C7 | −36.1 (3) |
O4—C4—C5—O5 | −58.1 (4) | O1—C7—C12—C11 | 121.7 (3) |
C3—C4—C5—O5 | −179.7 (3) | O2—C7—C12—C11 | −120.9 (3) |
O4—C4—C5—C6 | −177.2 (2) | C8—C7—C12—C11 | 1.0 (3) |
C3—C4—C5—C6 | 61.2 (4) | C10—C11—C14—C15 | −175.8 (3) |
O5—C5—C6—O6 | 59.9 (3) | C12—C11—C14—C15 | −64.9 (3) |
C4—C5—C6—O6 | −179.2 (2) | C10—C11—C14—C16 | 61.4 (3) |
O5—C5—C6—C1 | −175.7 (2) | C12—C11—C14—C16 | 172.3 (3) |
C4—C5—C6—C1 | −54.8 (4) | C10—C11—C14—C8 | −55.6 (3) |
O1—C1—C6—O6 | 58.8 (3) | C12—C11—C14—C8 | 55.3 (3) |
C2—C1—C6—O6 | 171.8 (2) | C13—C8—C14—C15 | −62.1 (4) |
O1—C1—C6—C5 | −67.7 (3) | C7—C8—C14—C15 | 65.0 (3) |
C2—C1—C6—C5 | 45.3 (4) | C9—C8—C14—C15 | 173.1 (3) |
C1—O1—C7—O2 | −34.2 (3) | C13—C8—C14—C16 | 61.6 (4) |
C1—O1—C7—C8 | −156.0 (3) | C7—C8—C14—C16 | −171.2 (3) |
C1—O1—C7—C12 | 87.3 (3) | C9—C8—C14—C16 | −63.1 (3) |
C2—O2—C7—O1 | 8.2 (3) | C13—C8—C14—C11 | 178.9 (3) |
C2—O2—C7—C8 | 129.0 (3) | C7—C8—C14—C11 | −53.9 (3) |
C2—O2—C7—C12 | −114.2 (3) | C9—C8—C14—C11 | 54.1 (3) |
O1—C7—C8—C13 | 40.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H60···O2i | 0.84 | 2.23 | 3.034 (3) | 159 |
O5—H5O···O3i | 0.84 | 2.12 | 2.752 (4) | 132 |
O4—H4O···O6ii | 0.84 | 2.11 | 2.951 (4) | 175 |
O3—H3O···O6ii | 0.84 | 2.18 | 2.964 (4) | 156 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, y+1, z. |
C16H26O6·3(H2O) | F(000) = 800 |
Mr = 368.42 | Dx = 1.301 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 4457 reflections |
a = 13.1708 (17) Å | θ = 3.0–26.3° |
b = 6.9513 (9) Å | µ = 0.11 mm−1 |
c = 20.737 (3) Å | T = 163 K |
β = 97.899 (2)° | Plate, colourless |
V = 1880.5 (4) Å3 | 0.73 × 0.40 × 0.12 mm |
Z = 4 |
Bruker P4 CCD area-detector diffractometer | 3205 independent reflections |
Radiation source: fine-focus sealed tube | 2697 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 2.0° |
ϕ and ω scans | h = −16→16 |
Absorption correction: multi-scan (Blessing, 1995) | k = −8→4 |
Tmin = 0.795, Tmax = 0.987 | l = −25→25 |
11666 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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0383P)2] where P = (Fo2 + 2Fc2)/3 |
3205 reflections | (Δ/σ)max = 0.001 |
345 parameters | Δρmax = 0.15 e Å−3 |
13 restraints | Δρmin = −0.14 e Å−3 |
C16H26O6·3(H2O) | V = 1880.5 (4) Å3 |
Mr = 368.42 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 13.1708 (17) Å | µ = 0.11 mm−1 |
b = 6.9513 (9) Å | T = 163 K |
c = 20.737 (3) Å | 0.73 × 0.40 × 0.12 mm |
β = 97.899 (2)° |
Bruker P4 CCD area-detector diffractometer | 3205 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 2697 reflections with I > 2σ(I) |
Tmin = 0.795, Tmax = 0.987 | Rint = 0.021 |
11666 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 13 restraints |
wR(F2) = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.15 e Å−3 |
3205 reflections | Δρmin = −0.14 e Å−3 |
345 parameters |
Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 0.8 mm diameter collimator was used. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.54094 (8) | 0.23695 (17) | 0.70402 (5) | 0.0285 (3) | |
O2 | 0.54811 (8) | 0.53515 (16) | 0.75079 (5) | 0.0303 (3) | |
O3 | 0.71153 (8) | 0.70282 (16) | 0.84148 (5) | 0.0295 (3) | |
H3O | 0.6573 | 0.7650 | 0.8304 | 0.044* | |
O4 | 0.67077 (8) | 0.48980 (16) | 0.95355 (5) | 0.0272 (3) | |
H4O | 0.6594 | 0.6064 | 0.9605 | 0.041* | |
O5 | 0.55353 (8) | 0.15423 (17) | 0.93618 (5) | 0.0271 (3) | |
H5O | 0.4956 | 0.2068 | 0.9319 | 0.041* | |
O6 | 0.55170 (8) | −0.04662 (17) | 0.81492 (5) | 0.0295 (3) | |
H6O | 0.5052 | −0.0880 | 0.8352 | 0.044* | |
O7 | 0.63963 (8) | 0.84532 (17) | 0.99827 (5) | 0.0296 (3) | |
H7A | 0.6964 (9) | 0.901 (3) | 1.0114 (9) | 0.044* | |
H7B | 0.6048 (13) | 0.933 (2) | 0.9767 (8) | 0.044* | |
O8 | 0.37384 (8) | 0.35812 (18) | 0.91942 (5) | 0.0288 (3) | |
H8A | 0.3232 (10) | 0.303 (3) | 0.8995 (8) | 0.043* | |
H8B | 0.3628 (14) | 0.368 (3) | 0.9577 (5) | 0.043* | |
O9 | 0.41424 (9) | 0.75506 (18) | 0.88054 (6) | 0.0368 (3) | |
H9OA | 0.4117 (15) | 0.782 (3) | 0.9196 (5) | 0.055* | |
H9OB | 0.4040 (15) | 0.6344 (15) | 0.8791 (9) | 0.055* | |
C1 | 0.61071 (11) | 0.2303 (2) | 0.76358 (7) | 0.0243 (3) | |
H1 | 0.6707 | 0.1465 | 0.7583 | 0.029* | |
C2 | 0.64377 (11) | 0.4384 (2) | 0.77078 (7) | 0.0255 (4) | |
H2 | 0.6927 | 0.4679 | 0.7393 | 0.031* | |
C3 | 0.68969 (11) | 0.5021 (2) | 0.83842 (7) | 0.0245 (4) | |
H3 | 0.7568 | 0.4338 | 0.8487 | 0.029* | |
C4 | 0.62357 (10) | 0.4388 (2) | 0.88919 (7) | 0.0218 (3) | |
H4A | 0.5550 | 0.5024 | 0.8801 | 0.026* | |
C5 | 0.60975 (10) | 0.2223 (2) | 0.88655 (7) | 0.0223 (3) | |
H5 | 0.6793 | 0.1620 | 0.8938 | 0.027* | |
C6 | 0.55645 (11) | 0.1571 (2) | 0.81982 (7) | 0.0228 (3) | |
H6 | 0.4848 | 0.2084 | 0.8137 | 0.027* | |
C7 | 0.4845 (2) | 0.4129 (5) | 0.70284 (15) | 0.0259 (8) | 0.685 (2) |
C8 | 0.47401 (17) | 0.4977 (4) | 0.63322 (10) | 0.0258 (6) | 0.685 (2) |
C9 | 0.4309 (3) | 0.3324 (6) | 0.58610 (19) | 0.0322 (9) | 0.685 (2) |
H9A | 0.4333 | 0.3684 | 0.5401 | 0.039* | 0.685 (2) |
H9B | 0.4701 | 0.2119 | 0.5959 | 0.039* | 0.685 (2) |
C10 | 0.31869 (19) | 0.3094 (4) | 0.59976 (12) | 0.0359 (7) | 0.685 (2) |
H10A | 0.2695 | 0.3348 | 0.5601 | 0.043* | 0.685 (2) |
H10B | 0.3064 | 0.1787 | 0.6159 | 0.043* | 0.685 (2) |
C11 | 0.30961 (17) | 0.4628 (4) | 0.65262 (11) | 0.0315 (6) | 0.685 (2) |
H11 | 0.2376 | 0.5014 | 0.6566 | 0.038* | 0.685 (2) |
C12 | 0.3703 (5) | 0.3898 (12) | 0.7158 (5) | 0.0294 (12) | 0.685 (2) |
H12A | 0.3539 | 0.2537 | 0.7238 | 0.035* | 0.685 (2) |
H12B | 0.3565 | 0.4685 | 0.7534 | 0.035* | 0.685 (2) |
C13 | 0.5711 (4) | 0.5890 (8) | 0.6159 (3) | 0.0374 (12) | 0.685 (2) |
H13A | 0.5945 | 0.6890 | 0.6478 | 0.056* | 0.685 (2) |
H13B | 0.5573 | 0.6467 | 0.5724 | 0.056* | 0.685 (2) |
H13C | 0.6244 | 0.4905 | 0.6161 | 0.056* | 0.685 (2) |
C14 | 0.37751 (18) | 0.6291 (4) | 0.63260 (11) | 0.0308 (6) | 0.685 (2) |
C15 | 0.3888 (4) | 0.7969 (6) | 0.6808 (3) | 0.0369 (11) | 0.685 (2) |
H15A | 0.4433 | 0.8830 | 0.6706 | 0.055* | 0.685 (2) |
H15B | 0.4063 | 0.7472 | 0.7251 | 0.055* | 0.685 (2) |
H15C | 0.3241 | 0.8680 | 0.6775 | 0.055* | 0.685 (2) |
C16 | 0.3384 (2) | 0.7162 (5) | 0.56494 (12) | 0.0435 (7) | 0.685 (2) |
H16A | 0.2702 | 0.7717 | 0.5655 | 0.065* | 0.685 (2) |
H16B | 0.3347 | 0.6151 | 0.5318 | 0.065* | 0.685 (2) |
H16C | 0.3857 | 0.8170 | 0.5547 | 0.065* | 0.685 (2) |
C7' | 0.5189 (5) | 0.4433 (9) | 0.6893 (3) | 0.029 (2) | 0.315 (2) |
C8' | 0.4036 (4) | 0.4928 (8) | 0.6737 (2) | 0.0281 (14) | 0.315 (2) |
C9' | 0.3924 (10) | 0.7122 (13) | 0.6795 (7) | 0.043 (3) | 0.315 (2) |
H91 | 0.4289 | 0.7588 | 0.7215 | 0.052* | 0.315 (2) |
H92 | 0.3193 | 0.7487 | 0.6765 | 0.052* | 0.315 (2) |
C10' | 0.4409 (5) | 0.7981 (9) | 0.6216 (3) | 0.054 (2) | 0.315 (2) |
H101 | 0.5010 | 0.8796 | 0.6369 | 0.065* | 0.315 (2) |
H102 | 0.3904 | 0.8740 | 0.5922 | 0.065* | 0.315 (2) |
C11' | 0.4726 (5) | 0.6114 (9) | 0.5882 (3) | 0.0425 (17) | 0.315 (2) |
H111 | 0.4826 | 0.6292 | 0.5417 | 0.051* | 0.315 (2) |
C12' | 0.5639 (11) | 0.5294 (17) | 0.6303 (5) | 0.038 (3) | 0.315 (2) |
H121 | 0.6148 | 0.6311 | 0.6444 | 0.046* | 0.315 (2) |
H122 | 0.5972 | 0.4285 | 0.6068 | 0.046* | 0.315 (2) |
C13' | 0.3375 (11) | 0.374 (3) | 0.7124 (12) | 0.054 (5) | 0.315 (2) |
H131 | 0.3507 | 0.2373 | 0.7060 | 0.081* | 0.315 (2) |
H132 | 0.2652 | 0.4023 | 0.6977 | 0.081* | 0.315 (2) |
H133 | 0.3538 | 0.4060 | 0.7587 | 0.081* | 0.315 (2) |
C14' | 0.3861 (5) | 0.4695 (10) | 0.5982 (2) | 0.0375 (15) | 0.315 (2) |
C15' | 0.4012 (8) | 0.2650 (14) | 0.5748 (5) | 0.046 (3) | 0.315 (2) |
H151 | 0.3473 | 0.1818 | 0.5876 | 0.069* | 0.315 (2) |
H152 | 0.4684 | 0.2173 | 0.5945 | 0.069* | 0.315 (2) |
H153 | 0.3977 | 0.2644 | 0.5273 | 0.069* | 0.315 (2) |
C16' | 0.2782 (5) | 0.5321 (10) | 0.5663 (3) | 0.0512 (18) | 0.315 (2) |
H161 | 0.2762 | 0.5358 | 0.5189 | 0.077* | 0.315 (2) |
H162 | 0.2629 | 0.6603 | 0.5822 | 0.077* | 0.315 (2) |
H163 | 0.2272 | 0.4400 | 0.5777 | 0.077* | 0.315 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0331 (6) | 0.0281 (7) | 0.0229 (5) | 0.0047 (5) | −0.0009 (4) | −0.0038 (5) |
O2 | 0.0378 (6) | 0.0273 (7) | 0.0229 (5) | 0.0084 (5) | −0.0059 (4) | −0.0041 (5) |
O3 | 0.0259 (5) | 0.0234 (7) | 0.0377 (6) | −0.0035 (5) | −0.0013 (4) | 0.0010 (5) |
O4 | 0.0327 (6) | 0.0228 (7) | 0.0242 (5) | 0.0021 (5) | −0.0026 (4) | −0.0029 (5) |
O5 | 0.0256 (5) | 0.0286 (7) | 0.0279 (5) | 0.0034 (5) | 0.0060 (4) | 0.0046 (5) |
O6 | 0.0318 (6) | 0.0230 (7) | 0.0341 (6) | −0.0027 (5) | 0.0061 (4) | −0.0023 (5) |
O7 | 0.0279 (6) | 0.0248 (7) | 0.0347 (6) | 0.0009 (5) | −0.0013 (5) | 0.0022 (5) |
O8 | 0.0237 (6) | 0.0346 (8) | 0.0281 (6) | −0.0026 (5) | 0.0035 (5) | −0.0049 (5) |
O9 | 0.0383 (6) | 0.0298 (8) | 0.0441 (7) | 0.0039 (6) | 0.0126 (5) | −0.0012 (6) |
C1 | 0.0232 (7) | 0.0253 (10) | 0.0237 (8) | 0.0040 (7) | 0.0013 (6) | −0.0020 (7) |
C2 | 0.0256 (8) | 0.0272 (10) | 0.0244 (8) | 0.0023 (7) | 0.0065 (6) | 0.0012 (7) |
C3 | 0.0202 (7) | 0.0225 (10) | 0.0301 (8) | 0.0025 (6) | 0.0010 (6) | 0.0017 (7) |
C4 | 0.0197 (7) | 0.0243 (9) | 0.0205 (7) | 0.0020 (6) | −0.0010 (6) | −0.0017 (6) |
C5 | 0.0195 (7) | 0.0234 (9) | 0.0238 (7) | 0.0036 (7) | 0.0025 (5) | 0.0018 (6) |
C6 | 0.0214 (7) | 0.0187 (9) | 0.0280 (8) | 0.0021 (7) | 0.0018 (6) | −0.0012 (7) |
C7 | 0.0258 (18) | 0.0316 (18) | 0.0210 (16) | 0.0061 (13) | 0.0060 (12) | −0.0075 (12) |
C8 | 0.0245 (12) | 0.0299 (16) | 0.0223 (12) | −0.0039 (11) | 0.0015 (9) | −0.0009 (11) |
C9 | 0.039 (2) | 0.035 (3) | 0.0218 (17) | −0.0014 (18) | 0.0013 (15) | 0.0016 (16) |
C10 | 0.0344 (14) | 0.0357 (18) | 0.0344 (13) | −0.0042 (12) | −0.0070 (11) | −0.0036 (12) |
C11 | 0.0247 (12) | 0.0390 (17) | 0.0293 (12) | 0.0000 (11) | −0.0014 (9) | −0.0010 (11) |
C12 | 0.036 (3) | 0.027 (2) | 0.0256 (19) | −0.002 (2) | 0.005 (2) | 0.0023 (14) |
C13 | 0.0357 (18) | 0.048 (3) | 0.029 (3) | −0.006 (2) | 0.0091 (16) | 0.0106 (17) |
C14 | 0.0326 (13) | 0.0321 (17) | 0.0260 (13) | 0.0019 (11) | −0.0024 (10) | 0.0000 (13) |
C15 | 0.042 (2) | 0.035 (3) | 0.0316 (17) | 0.012 (2) | −0.0031 (13) | −0.002 (3) |
C16 | 0.0512 (16) | 0.0413 (19) | 0.0348 (14) | 0.0068 (14) | −0.0056 (11) | 0.0037 (12) |
C7' | 0.027 (4) | 0.045 (5) | 0.017 (3) | 0.012 (3) | 0.012 (3) | −0.009 (3) |
C8' | 0.038 (3) | 0.020 (3) | 0.022 (2) | 0.005 (2) | −0.011 (2) | −0.005 (2) |
C9' | 0.045 (4) | 0.032 (7) | 0.046 (5) | 0.011 (5) | −0.017 (3) | −0.010 (6) |
C10' | 0.070 (4) | 0.030 (4) | 0.053 (4) | −0.009 (3) | −0.026 (3) | 0.006 (3) |
C11' | 0.062 (4) | 0.033 (4) | 0.030 (3) | −0.008 (3) | −0.002 (3) | 0.008 (3) |
C12' | 0.066 (6) | 0.035 (7) | 0.014 (4) | −0.020 (5) | 0.005 (4) | 0.003 (4) |
C13' | 0.059 (10) | 0.063 (8) | 0.041 (6) | 0.002 (8) | 0.012 (8) | −0.013 (5) |
C14' | 0.054 (4) | 0.029 (4) | 0.026 (3) | −0.002 (3) | −0.005 (2) | 0.002 (3) |
C15' | 0.058 (6) | 0.036 (6) | 0.040 (4) | −0.010 (4) | −0.011 (4) | 0.002 (4) |
C16' | 0.056 (4) | 0.046 (5) | 0.041 (3) | 0.011 (3) | −0.030 (3) | −0.004 (3) |
O1—C7 | 1.430 (3) | C11—C12 | 1.524 (8) |
O1—C1 | 1.4352 (16) | C11—C14 | 1.553 (4) |
O1—C7' | 1.487 (6) | C11—H11 | 1.0000 |
O2—C7' | 1.431 (6) | C12—H12A | 0.9900 |
O2—C2 | 1.4380 (18) | C12—H12B | 0.9900 |
O2—C7 | 1.477 (3) | C13—H13A | 0.9800 |
O3—C3 | 1.425 (2) | C13—H13B | 0.9800 |
O3—H3O | 0.8400 | C13—H13C | 0.9800 |
O4—C4 | 1.4370 (16) | C14—C15 | 1.530 (5) |
O4—H4O | 0.8400 | C14—C16 | 1.550 (3) |
O5—C5 | 1.4286 (17) | C15—H15A | 0.9800 |
O5—H5O | 0.8400 | C15—H15B | 0.9800 |
O6—C6 | 1.420 (2) | C15—H15C | 0.9800 |
O6—H6O | 0.8400 | C16—H16A | 0.9800 |
O7—H7A | 0.852 (10) | C16—H16B | 0.9800 |
O7—H7B | 0.852 (10) | C16—H16C | 0.9800 |
O8—H8A | 0.827 (9) | C7'—C8' | 1.547 (8) |
O8—H8B | 0.830 (9) | C7'—C12' | 1.552 (11) |
O9—H9OA | 0.837 (9) | C8'—C13' | 1.51 (2) |
O9—H9OB | 0.849 (10) | C8'—C9' | 1.538 (10) |
C1—C2 | 1.512 (2) | C8'—C14' | 1.560 (7) |
C1—C6 | 1.536 (2) | C9'—C10' | 1.553 (15) |
C1—H1 | 1.0000 | C9'—H91 | 0.9900 |
C2—C3 | 1.515 (2) | C9'—H92 | 0.9900 |
C2—H2 | 1.0000 | C10'—C11' | 1.555 (9) |
C3—C4 | 1.5204 (19) | C10'—H101 | 0.9900 |
C3—H3 | 1.0000 | C10'—H102 | 0.9900 |
C4—C5 | 1.516 (2) | C11'—C12' | 1.498 (15) |
C4—H4A | 1.0000 | C11'—C14' | 1.542 (9) |
C5—C6 | 1.532 (2) | C11'—H111 | 1.0000 |
C5—H5 | 1.0000 | C12'—H121 | 0.9900 |
C6—H6 | 1.0000 | C12'—H122 | 0.9900 |
C7—C8 | 1.548 (4) | C13'—H131 | 0.9800 |
C7—C12 | 1.572 (7) | C13'—H132 | 0.9800 |
C8—C13 | 1.515 (5) | C13'—H133 | 0.9800 |
C8—C14 | 1.564 (3) | C14'—C15' | 1.523 (11) |
C8—C9 | 1.564 (4) | C14'—C16' | 1.544 (8) |
C9—C10 | 1.550 (5) | C15'—H151 | 0.9800 |
C9—H9A | 0.9900 | C15'—H152 | 0.9800 |
C9—H9B | 0.9900 | C15'—H153 | 0.9800 |
C10—C11 | 1.545 (4) | C16'—H161 | 0.9800 |
C10—H10A | 0.9900 | C16'—H162 | 0.9800 |
C10—H10B | 0.9900 | C16'—H163 | 0.9800 |
C7—O1—C1 | 108.18 (15) | C10—C11—H11 | 114.2 |
C1—O1—C7' | 106.9 (3) | C14—C11—H11 | 114.2 |
C7'—O2—C2 | 99.5 (3) | C11—C12—C7 | 102.7 (5) |
C2—O2—C7 | 108.57 (16) | C11—C12—H12A | 111.2 |
C3—O3—H3O | 109.5 | C7—C12—H12A | 111.2 |
C4—O4—H4O | 109.5 | C11—C12—H12B | 111.2 |
C5—O5—H5O | 109.5 | C7—C12—H12B | 111.2 |
C6—O6—H6O | 109.5 | H12A—C12—H12B | 109.1 |
H7A—O7—H7B | 103.2 (19) | C15—C14—C16 | 106.5 (3) |
H8A—O8—H8B | 106.4 (18) | C15—C14—C11 | 113.7 (3) |
H9OA—O9—H9OB | 103 (2) | C16—C14—C11 | 113.7 (2) |
O1—C1—C2 | 101.29 (12) | C15—C14—C8 | 115.7 (3) |
O1—C1—C6 | 110.76 (11) | C16—C14—C8 | 113.8 (2) |
C2—C1—C6 | 113.56 (13) | C11—C14—C8 | 93.5 (2) |
O1—C1—H1 | 110.3 | O2—C7'—O1 | 103.1 (4) |
C2—C1—H1 | 110.3 | O2—C7'—C8' | 102.8 (4) |
C6—C1—H1 | 110.3 | O1—C7'—C8' | 114.6 (5) |
O2—C2—C1 | 100.94 (12) | O2—C7'—C12' | 116.5 (6) |
O2—C2—C3 | 110.66 (12) | O1—C7'—C12' | 116.7 (6) |
C1—C2—C3 | 116.33 (13) | C8'—C7'—C12' | 102.7 (7) |
O2—C2—H2 | 109.5 | C13'—C8'—C9' | 115.6 (11) |
C1—C2—H2 | 109.5 | C13'—C8'—C7' | 112.9 (8) |
C3—C2—H2 | 109.5 | C9'—C8'—C7' | 107.9 (6) |
O3—C3—C2 | 112.31 (12) | C13'—C8'—C14' | 117.4 (10) |
O3—C3—C4 | 112.57 (12) | C9'—C8'—C14' | 100.3 (6) |
C2—C3—C4 | 111.28 (12) | C7'—C8'—C14' | 101.1 (4) |
O3—C3—H3 | 106.7 | C8'—C9'—C10' | 105.5 (8) |
C2—C3—H3 | 106.7 | C8'—C9'—H91 | 110.6 |
C4—C3—H3 | 106.7 | C10'—C9'—H91 | 110.6 |
O4—C4—C5 | 108.22 (12) | C8'—C9'—H92 | 110.6 |
O4—C4—C3 | 110.85 (11) | C10'—C9'—H92 | 110.6 |
C5—C4—C3 | 109.84 (12) | H91—C9'—H92 | 108.8 |
O4—C4—H4A | 109.3 | C9'—C10'—C11' | 100.8 (5) |
C5—C4—H4A | 109.3 | C9'—C10'—H101 | 111.6 |
C3—C4—H4A | 109.3 | C11'—C10'—H101 | 111.6 |
O5—C5—C4 | 111.99 (12) | C9'—C10'—H102 | 111.6 |
O5—C5—C6 | 109.52 (12) | C11'—C10'—H102 | 111.6 |
C4—C5—C6 | 111.37 (12) | H101—C10'—H102 | 109.4 |
O5—C5—H5 | 107.9 | C12'—C11'—C14' | 103.2 (6) |
C4—C5—H5 | 107.9 | C12'—C11'—C10' | 107.5 (7) |
C6—C5—H5 | 107.9 | C14'—C11'—C10' | 103.0 (5) |
O6—C6—C5 | 111.72 (12) | C12'—C11'—H111 | 114.0 |
O6—C6—C1 | 107.25 (12) | C14'—C11'—H111 | 114.0 |
C5—C6—C1 | 112.62 (12) | C10'—C11'—H111 | 114.0 |
O6—C6—H6 | 108.4 | C11'—C12'—C7' | 104.0 (9) |
C5—C6—H6 | 108.4 | C11'—C12'—H121 | 110.9 |
C1—C6—H6 | 108.4 | C7'—C12'—H121 | 110.9 |
O1—C7—O2 | 103.6 (2) | C11'—C12'—H122 | 110.9 |
O1—C7—C8 | 108.7 (2) | C7'—C12'—H122 | 110.9 |
O2—C7—C8 | 112.3 (2) | H121—C12'—H122 | 109.0 |
O1—C7—C12 | 114.6 (4) | C8'—C13'—H131 | 109.5 |
O2—C7—C12 | 114.3 (4) | C8'—C13'—H132 | 109.5 |
C8—C7—C12 | 103.5 (4) | H131—C13'—H132 | 109.5 |
C13—C8—C7 | 114.3 (3) | C8'—C13'—H133 | 109.5 |
C13—C8—C14 | 117.7 (3) | H131—C13'—H133 | 109.5 |
C7—C8—C14 | 101.43 (18) | H132—C13'—H133 | 109.5 |
C13—C8—C9 | 113.9 (3) | C15'—C14'—C11' | 115.0 (7) |
C7—C8—C9 | 106.3 (2) | C15'—C14'—C16' | 106.3 (6) |
C14—C8—C9 | 101.5 (2) | C11'—C14'—C16' | 114.5 (5) |
C10—C9—C8 | 103.6 (3) | C15'—C14'—C8' | 114.1 (6) |
C10—C9—H9A | 111.0 | C11'—C14'—C8' | 93.3 (4) |
C8—C9—H9A | 111.0 | C16'—C14'—C8' | 113.6 (5) |
C10—C9—H9B | 111.0 | C14'—C15'—H151 | 109.5 |
C8—C9—H9B | 111.0 | C14'—C15'—H152 | 109.5 |
H9A—C9—H9B | 109.0 | H151—C15'—H152 | 109.5 |
C11—C10—C9 | 103.1 (2) | C14'—C15'—H153 | 109.5 |
C11—C10—H10A | 111.1 | H151—C15'—H153 | 109.5 |
C9—C10—H10A | 111.1 | H152—C15'—H153 | 109.5 |
C11—C10—H10B | 111.1 | C14'—C16'—H161 | 109.5 |
C9—C10—H10B | 111.1 | C14'—C16'—H162 | 109.5 |
H10A—C10—H10B | 109.1 | H161—C16'—H162 | 109.5 |
C12—C11—C10 | 107.3 (4) | C14'—C16'—H163 | 109.5 |
C12—C11—C14 | 102.9 (3) | H161—C16'—H163 | 109.5 |
C10—C11—C14 | 102.73 (19) | H162—C16'—H163 | 109.5 |
C12—C11—H11 | 114.2 | ||
C7—O1—C1—C2 | −37.82 (18) | C8—C7—C12—C11 | 0.2 (6) |
C7'—O1—C1—C2 | −12.9 (3) | C12—C11—C14—C15 | −64.1 (5) |
C7—O1—C1—C6 | 82.95 (19) | C10—C11—C14—C15 | −175.5 (3) |
C7'—O1—C1—C6 | 107.9 (3) | C12—C11—C14—C16 | 173.9 (4) |
C7'—O2—C2—C1 | −52.8 (3) | C10—C11—C14—C16 | 62.5 (3) |
C7—O2—C2—C1 | −30.02 (18) | C12—C11—C14—C8 | 56.0 (4) |
C7'—O2—C2—C3 | −176.6 (3) | C10—C11—C14—C8 | −55.4 (2) |
C7—O2—C2—C3 | −153.79 (17) | C13—C8—C14—C15 | −61.9 (4) |
O1—C1—C2—O2 | 40.49 (13) | C7—C8—C14—C15 | 63.6 (3) |
C6—C1—C2—O2 | −78.29 (14) | C9—C8—C14—C15 | 173.1 (3) |
O1—C1—C2—C3 | 160.26 (11) | C13—C8—C14—C16 | 61.9 (4) |
C6—C1—C2—C3 | 41.49 (17) | C7—C8—C14—C16 | −172.6 (2) |
O2—C2—C3—O3 | −61.31 (16) | C9—C8—C14—C16 | −63.1 (3) |
C1—C2—C3—O3 | −175.70 (12) | C13—C8—C14—C11 | 179.7 (3) |
O2—C2—C3—C4 | 65.91 (17) | C7—C8—C14—C11 | −54.8 (2) |
C1—C2—C3—C4 | −48.48 (17) | C9—C8—C14—C11 | 54.7 (2) |
O3—C3—C4—O4 | −56.34 (15) | C2—O2—C7'—O1 | 44.4 (4) |
C2—C3—C4—O4 | 176.58 (13) | C7—O2—C7'—O1 | −70.3 (7) |
O3—C3—C4—C5 | −175.89 (11) | C2—O2—C7'—C8' | 163.8 (3) |
C2—C3—C4—C5 | 57.03 (15) | C7—O2—C7'—C8' | 49.1 (7) |
O4—C4—C5—O5 | 55.12 (14) | C2—O2—C7'—C12' | −84.8 (7) |
C3—C4—C5—O5 | 176.26 (10) | C7—O2—C7'—C12' | 160.5 (13) |
O4—C4—C5—C6 | 178.15 (11) | C7—O1—C7'—O2 | 77.7 (7) |
C3—C4—C5—C6 | −60.71 (14) | C1—O1—C7'—O2 | −19.1 (4) |
O5—C5—C6—O6 | −61.00 (15) | C7—O1—C7'—C8' | −33.3 (6) |
C4—C5—C6—O6 | 174.57 (11) | C1—O1—C7'—C8' | −130.0 (4) |
O5—C5—C6—C1 | 178.22 (12) | C7—O1—C7'—C12' | −153.3 (13) |
C4—C5—C6—C1 | 53.78 (16) | C1—O1—C7'—C12' | 109.9 (7) |
O1—C1—C6—O6 | 80.25 (15) | O2—C7'—C8'—C13' | −76.3 (12) |
C2—C1—C6—O6 | −166.57 (11) | O1—C7'—C8'—C13' | 34.8 (12) |
O1—C1—C6—C5 | −156.44 (12) | C12'—C7'—C8'—C13' | 162.3 (12) |
C2—C1—C6—C5 | −43.26 (17) | O2—C7'—C8'—C9' | 52.7 (7) |
C1—O1—C7—O2 | 19.5 (2) | O1—C7'—C8'—C9' | 163.7 (6) |
C7'—O1—C7—O2 | −71.4 (8) | C12'—C7'—C8'—C9' | −68.7 (8) |
C1—O1—C7—C8 | 139.02 (18) | O2—C7'—C8'—C14' | 157.4 (4) |
C7'—O1—C7—C8 | 48.1 (7) | O1—C7'—C8'—C14' | −91.5 (5) |
C1—O1—C7—C12 | −105.7 (4) | C12'—C7'—C8'—C14' | 36.1 (7) |
C7'—O1—C7—C12 | 163.4 (10) | C13'—C8'—C9'—C10' | −163.7 (10) |
C7'—O2—C7—O1 | 78.8 (8) | C7'—C8'—C9'—C10' | 68.9 (8) |
C2—O2—C7—O1 | 7.9 (2) | C14'—C8'—C9'—C10' | −36.4 (8) |
C7'—O2—C7—C8 | −38.3 (8) | C8'—C9'—C10'—C11' | 1.2 (9) |
C2—O2—C7—C8 | −109.2 (2) | C9'—C10'—C11'—C12' | −73.3 (8) |
C7'—O2—C7—C12 | −155.8 (10) | C9'—C10'—C11'—C14' | 35.3 (7) |
C2—O2—C7—C12 | 133.4 (4) | C14'—C11'—C12'—C7' | −34.7 (9) |
O1—C7—C8—C13 | −75.0 (4) | C10'—C11'—C12'—C7' | 73.8 (8) |
O2—C7—C8—C13 | 39.0 (4) | O2—C7'—C12'—C11' | −112.8 (7) |
C12—C7—C8—C13 | 162.7 (5) | O1—C7'—C12'—C11' | 124.9 (8) |
O1—C7—C8—C14 | 157.3 (2) | C8'—C7'—C12'—C11' | −1.3 (9) |
O2—C7—C8—C14 | −88.7 (2) | C12'—C11'—C14'—C15' | −63.3 (8) |
C12—C7—C8—C14 | 35.0 (4) | C10'—C11'—C14'—C15' | −175.2 (6) |
O1—C7—C8—C9 | 51.6 (3) | C12'—C11'—C14'—C16' | 173.1 (7) |
O2—C7—C8—C9 | 165.6 (2) | C10'—C11'—C14'—C16' | 61.3 (6) |
C12—C7—C8—C9 | −70.7 (4) | C12'—C11'—C14'—C8' | 55.2 (8) |
C13—C8—C9—C10 | −162.7 (3) | C10'—C11'—C14'—C8' | −56.6 (5) |
C7—C8—C9—C10 | 70.6 (3) | C13'—C8'—C14'—C15' | −58.9 (12) |
C14—C8—C9—C10 | −35.1 (3) | C9'—C8'—C14'—C15' | 175.0 (8) |
C8—C9—C10—C11 | 0.1 (3) | C7'—C8'—C14'—C15' | 64.4 (7) |
C9—C10—C11—C12 | −72.7 (4) | C13'—C8'—C14'—C11' | −178.2 (10) |
C9—C10—C11—C14 | 35.4 (3) | C9'—C8'—C14'—C11' | 55.7 (7) |
C10—C11—C12—C7 | 72.2 (5) | C7'—C8'—C14'—C11' | −55.0 (5) |
C14—C11—C12—C7 | −35.8 (6) | C13'—C8'—C14'—C16' | 63.2 (11) |
O1—C7—C12—C11 | −118.1 (4) | C9'—C8'—C14'—C16' | −62.9 (8) |
O2—C7—C12—C11 | 122.5 (5) | C7'—C8'—C14'—C16' | −173.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O6i | 0.84 | 1.91 | 2.7294 (16) | 167 |
O4—H4O···O7 | 0.84 | 1.87 | 2.6908 (16) | 165 |
O5—H5O···O8 | 0.84 | 1.91 | 2.7394 (16) | 172 |
O6—H6O···O9ii | 0.84 | 1.95 | 2.7762 (17) | 166 |
O7—H7A···O4iii | 0.85 (2) | 1.90 (1) | 2.7490 (16) | 172 (2) |
O7—H7B···O5i | 0.85 (2) | 1.84 (2) | 2.6746 (16) | 168 (2) |
O8—H8A···O3iv | 0.83 (2) | 1.90 (2) | 2.7199 (16) | 170 (2) |
O8—H8B···O4v | 0.83 (1) | 2.13 (1) | 2.9236 (15) | 161 (2) |
O9—H9OA···O7v | 0.84 (1) | 1.97 (1) | 2.7754 (17) | 162 (2) |
O9—H9OB···O8 | 0.85 (1) | 2.15 (1) | 2.9436 (18) | 155 (2) |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+3/2, y+1/2, −z+2; (iv) x−1/2, y−1/2, z; (v) −x+1, y, −z+2. |
Experimental details
(A) | (B) | |
Crystal data | ||
Chemical formula | C16H26O6 | C16H26O6·3(H2O) |
Mr | 314.37 | 368.42 |
Crystal system, space group | Monoclinic, C2 | Monoclinic, C2 |
Temperature (K) | 169 | 163 |
a, b, c (Å) | 12.700 (3), 6.9721 (17), 18.422 (5) | 13.1708 (17), 6.9513 (9), 20.737 (3) |
β (°) | 107.275 (3) | 97.899 (2) |
V (Å3) | 1557.7 (7) | 1880.5 (4) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.11 |
Crystal size (mm) | 0.47 × 0.33 × 0.03 | 0.73 × 0.40 × 0.12 |
Data collection | ||
Diffractometer | Bruker-Nonius APEX2 CCD area-detector diffractometer | Bruker P4 CCD area-detector diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.796, 0.997 | 0.795, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8809, 2953, 2026 | 11666, 3205, 2697 |
Rint | 0.055 | 0.021 |
(sin θ/λ)max (Å−1) | 0.627 | 0.626 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.113, 1.08 | 0.027, 0.059, 0.96 |
No. of reflections | 2953 | 3205 |
No. of parameters | 206 | 345 |
No. of restraints | 1 | 13 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.26 | 0.15, −0.14 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 2003), SHELXL97 and PLATON (Spek, 2003).
O1—C7 | 1.441 (4) | O2—C7 | 1.466 (4) |
O1—C1 | 1.451 (4) | C1—C2 | 1.531 (5) |
O2—C2 | 1.458 (4) | C7—C8 | 1.562 (5) |
C7—O1—C1 | 104.5 (2) | O1—C1—C6 | 112.0 (2) |
C2—O2—C7 | 108.2 (2) | O2—C7—C8 | 112.8 (3) |
O1—C1—C2 | 100.2 (2) | O1—C7—C12 | 113.0 (3) |
C7—O2—C2—C1 | 19.2 (3) | C2—O2—C7—C12 | −114.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H60···O2i | 0.84 | 2.23 | 3.034 (3) | 159 |
O5—H5O···O3i | 0.84 | 2.12 | 2.752 (4) | 132 |
O4—H4O···O6ii | 0.84 | 2.11 | 2.951 (4) | 175 |
O3—H3O···O6ii | 0.84 | 2.18 | 2.964 (4) | 156 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, y+1, z. |
O1—C7 | 1.430 (3) | O2—C2 | 1.4380 (18) |
O1—C1 | 1.4352 (16) | O2—C7 | 1.477 (3) |
O1—C7' | 1.487 (6) | O4—C4 | 1.4370 (16) |
O2—C7' | 1.431 (6) | O6—C6 | 1.420 (2) |
C7—O1—C1 | 108.18 (15) | C1—O1—C7' | 106.9 (3) |
C7—O1—C1—C2 | −37.82 (18) | C8—C9—C10—C11 | 0.1 (3) |
C7'—O1—C1—C2 | −12.9 (3) | C7—O1—C7'—C12' | −153.3 (13) |
C1—O1—C7—C12 | −105.7 (4) | C8'—C9'—C10'—C11' | 1.2 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O6i | 0.84 | 1.91 | 2.7294 (16) | 167 |
O4—H4O···O7 | 0.84 | 1.87 | 2.6908 (16) | 165 |
O5—H5O···O8 | 0.84 | 1.91 | 2.7394 (16) | 172 |
O6—H6O···O9ii | 0.84 | 1.95 | 2.7762 (17) | 166 |
O7—H7A···O4iii | 0.853 (15) | 1.903 (14) | 2.7490 (16) | 172 (2) |
O7—H7B···O5i | 0.852 (15) | 1.836 (15) | 2.6746 (16) | 168 (2) |
O8—H8A···O3iv | 0.829 (16) | 1.900 (16) | 2.7199 (16) | 170 (2) |
O8—H8B···O4v | 0.829 (11) | 2.127 (14) | 2.9236 (15) | 161 (2) |
O9—H9OA···O7v | 0.837 (12) | 1.967 (14) | 2.7754 (17) | 162 (2) |
O9—H9OB···O8 | 0.849 (11) | 2.153 (13) | 2.9436 (18) | 155 (2) |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+3/2, y+1/2, −z+2; (iv) x−1/2, y−1/2, z; (v) −x+1, y, −z+2. |
Sourcea | Ring#b | Q | θ | ϕ | Conformation |
I | 1 | 0.550 (4) | 13.8 (4) | 190.2 (17) | Distorted Chair 2C5 |
II,III | 1 | 0.5276 (14) | 165.87 (15) | 17.8 (6) | Distorted Chairc 1C4 |
I | 2A | 0.429 (3) | na | 206.1 (5) | Twist, 2T1 |
II | 2A | 0.392 (2) | na | 46.2 (3) | Twist, 2T3 |
III | 2B | 0.492 (3) | na | 92.8 (4) | Twist, 3T4 |
I | 3A | 0.999 (4) | 89.5 (2) | 59.9 (2) | Boat B2,5 |
II | 3A | 0.990 (4) | 89.2 (3) | 59.9 (2) | Boat B2,5 |
III | 3B | 0.981 (8) | 89.1 (6) | 57.0 (5) | Boat B2,5 |
I | 4A | 0.590 (4) | na | 253.1 (4) | Envelope on 3E |
II | 4A | 0.593 (5) | na | 252.0 (5) | Envelope 3E |
III | 4B | 0.588 (8) | na | 250.2 (8) | Envelope 3E |
I | 5A | 0.594 (4) | na | 323.7 (3) | Envelope 5E |
II | 5A | 0.592 (3) | na | 324.3 (3) | Envelope 5E |
III | 5B | 0.601 (9) | na | 324.6 (8) | Envelope on 5E |
Notes:
(a) Structure. (b) (1) C1–C6, (2A) O1/C1/C2/O2/C7, (2B) O1/C1/C2/O2/C7', (3A) C7–C12, (3B) C7'–C12', (4A) C7/C8/C14/C11/C12, (4B) C7'/C8'/C14'/C11'/C12', (5A) C8–C11/C14, (5B) C8'–C11'/C14'. (c) Note: opposite absolute confguration: 180-θ, 180 + ϕ. |
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The title compounds were studied as part of a programme to prepare chiral inositol derivatives (Baars & Hoberg, 2006; Cousins et al., 2004). The structure of (I) (see scheme) was noted (Pietrusiewicz et al., 1992) but no structural parameters have been reported. Previous studies of myo-inositol derivatives as listed in the Cambridge Structural Database [Allen, 2002; CSD Version 5.27 (updated August 2006); refcodes are given in capitals] indicate that these molecules frequently show novel conformational/packing effects, e.g. molecular dynamics simulation confirming two stable conformations (XADWII; Dillen et al., 2000) and `thermosalient behaviour' (HADKIG; Steiner et al., 1993). The camphor unit (bicyclo[2.2.1]heptane) has been found to be invariant (Clegg et al., 1995). Along with the structure of (I) (crystal A), we report a novel structure containing cocrystallized (II) and (III) (crystal B) in a ratio corresponding approximately to their relative concentrations in solution as determined by NMR. In both cases, the L-camphor used in the synthesis determined the absolute configuration assigned here, since anomalous dispersion affects, as expected, were insufficient [e.g. the Flack parameter for crystal B was -0.2 (7)]. Friedel pairs in the data have been retained for future reference purposes.
The asymmetric unit in each crystal contains one independent myo-inositol-1,2-camphor acetal unit (Figs. 1–3); in crystal B, there are also three water molecules. For crystal A (I) the inositol fragment absolute configuration of C1(S), C2(R), C3(R), C4(S), C5(S), C6(R), and for crystal B the opposite [C1(R), C2(S), C3(S), C4(R), C5(R), C6(S)], was determined from the chemical synthesis based on L-camphor. In both crystals, the acetal linkages to the myo-inositol unit are similar to those observed previously [TEKPUU (Spiers et al., 1996), NOZCIO (Spiers et al., 1997), PINMEE and PINMII (Chung et al., 1994)]. For (I) the five-membered link stereochemistry (O1/C1/C2/O2/C7) to the L-camphor unit is simlar to that reported for the dihydroxybutanedioic acid dimethyl ester (NAFWEW; Mikolajczyk et al., 1996).
The L-camphor unit is present in crystal B in two sites corresponding to the two alternative configurations of attachment at the C7 atoms [(II) and (III) in the scheme]; the two are distinguished by primed and unprimed labels (Figs. 2 and 3). An initial refinement of the primed and unprimed atoms with one common isotropic U factor and freely refined occupancies indicated unambiguously that only these two related stereoisomers were present; the two sets were then grouped and refined to a final stereoisomer ratio of 0.685 (2):0.315 (2). The four C7,C7'—O1,O2 distances were refined to a common dimension, giving the results in Table 3 (see Experimental). The observed ratio in solution from NMR was 75:25 in DMSO-d6. We determined the relative electronic energies (gas phase) using the Amsterdam Density Functional program system (SCM, 2006) [with VWN local density approximation (Vosko et al., 1980)] optimizing the structures and starting from the X-ray coordinate positions. The difference between the stereoisomers (II) and (III) was 0.45 kcal mol-1, in good agreement with both solid state and solution observations. Compound (I) was estimated to be less stable than (II) by 11 kcal mol-1, somewhat larger than expected.
In all structures, the inositol ring adopts a slightly flattened chair conformation, as shown by the Cremer & Pople (1975) parameters (Table 5). In (I), the best `arms' of the chair are atoms C1, C6, C3 and C4 [the mean out-of-plane distance is 0.014 (2) Å], with atoms C2 and C5 lying 0.528 (4) and -0.727 (5) Å from the plane; for crystal B [(II) and (III)], the corresponding best parameters are C2, C3, C5 and C6 [0.0193 (8) Å], with C1 and C4 at 0.513 (2) and -0.696 (2) Å. The five-membered rings O1/C1/C2/O2/C7(C7') (rings 2A and 2B; Table 5) adopt twist conformations (Evans & Boeyens, 1989). The L-camphor fused rings adopt envelope or boat configurations for the five- and six-membered rings, respectively, as expected (Clegg et al., 1995).
The cystal packing (Tables 2 and 4) can be described as similar two-dimensional layers normal to the c axis (Figs. 4 and 5). These layers are formed from strong O—H···O hydrogen interactions involving all inositol O atoms in A, and both inositol and water O atoms in crystal B as acceptors. The L-camphor rings pack `head-to-head' separating the layers. The close C—H···O interactions in crystal B (not listed in Table 4) are regarded as fortuitous [even though they fulfil the normal criteria (Desiraju & Steiner, 1999)], because of their location and the availability of the acceptor O atoms (Fig. 5). There is also a fortuitous short contact (O—H4···H6O 1.99 Å) in (I) between two H atoms involved in strong hydrogen bonds (Table 2).