Two polymorphs of the title compound, (4R,5R,6R,7R)-4,7-bis(hydroxymethyl)-1,3-dioxepane-5,6-diol, C7H14O6, both have Z' = 2 at 100 K, and differ in their hydrogen-bonding patterns. The sodium iodide complex, NaI·C7H14O6, is isomorphous with the NaCl complex, and has the mannitol, cation and anion all lying on twofold axes. The dioxepane rings of all three molecules are in the twist-chair conformation.
Supporting information
CCDC references: 163890; 163891; 163892
For all compounds, data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS. Data reduction: maXus (Mackay et al., 1999) for (I); XCAD4 (Harms & Wocadlo, 1995) for (II), (III). Program(s) used to solve structure: SIR92 (Altomare et al., 1993) for (I); SHELXS97 (Sheldrick, 1997) for (II), (III). For all compounds, 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 for (I); WinGX publication routines (Farrugia, 1998) for (II), (III).
(I) 4(
R),7(
R)-di-(hydroxymethyl)-5(
R),6(
R)-dihydroxy-1,3-dioxepane
top
Crystal data top
C7H14O6 | F(000) = 416 |
Mr = 194.18 | Dx = 1.512 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.5100 (4) Å | Cell parameters from 25 reflections |
b = 14.462 (1) Å | θ = 9.7–18.3° |
c = 13.231 (1) Å | µ = 0.13 mm−1 |
β = 98.823 (7)° | T = 100 K |
V = 852.76 (12) Å3 | Needle fragment, colorless |
Z = 4 | 0.37 × 0.35 × 0.25 mm |
Data collection top
Enraf-Nonius CAD4 (with Oxford Cryostream) diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 45.0°, θmin = 2.8° |
Graphite monochromator | h = 0→8 |
ω–2θ scans | k = 0→28 |
7174 measured reflections | l = −26→25 |
7174 independent reflections | 3 standard reflections every 60 min |
5701 reflections with I > 2σ(I) | intensity decay: 5.3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.5679P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
7174 reflections | Δρmax = 0.70 e Å−3 |
236 parameters | Δρmin = −0.52 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (3) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.3164 (3) | 0.00009 (11) | 0.17474 (10) | 0.0163 (2) | |
H1OA | 0.1524 | 0.0046 | 0.1352 | 0.024* | |
O2A | 0.0397 (3) | 0.14935 (9) | 0.25554 (9) | 0.01210 (19) | |
O3A | 0.4104 (3) | 0.04236 (11) | 0.49076 (10) | 0.0160 (2) | |
H3OA | 0.3164 | 0.0080 | 0.5260 | 0.024* | |
O4A | 0.0748 (4) | 0.18711 (12) | 0.56764 (10) | 0.0185 (3) | |
H4OA | 0.1833 | 0.2105 | 0.6185 | 0.028* | |
O5A | 0.2358 (3) | 0.28832 (9) | 0.32870 (10) | 0.0129 (2) | |
O6A | −0.0941 (4) | 0.43415 (10) | 0.40284 (12) | 0.0171 (2) | |
H6OA | 0.0237 | 0.4611 | 0.3692 | 0.026* | |
C1A | 0.2625 (5) | 0.00079 (13) | 0.27831 (14) | 0.0149 (3) | |
H1A1 | 0.4167 | −0.0370 | 0.3210 | 0.018* | |
H1A2 | 0.0637 | −0.0268 | 0.2821 | 0.018* | |
C2A | 0.2717 (4) | 0.09886 (12) | 0.31908 (12) | 0.0112 (2) | |
H2A | 0.4719 | 0.1274 | 0.3157 | 0.013* | |
C3A | 0.2039 (4) | 0.10155 (12) | 0.42887 (12) | 0.0113 (2) | |
H3A | −0.0025 | 0.0762 | 0.4285 | 0.014* | |
C4A | 0.2174 (4) | 0.19724 (12) | 0.47948 (12) | 0.0119 (2) | |
H4A | 0.4324 | 0.2141 | 0.5020 | 0.014* | |
C5A | 0.0665 (4) | 0.27455 (12) | 0.41088 (12) | 0.0117 (2) | |
H5A | −0.1441 | 0.2565 | 0.3828 | 0.014* | |
C6A | 0.0671 (5) | 0.36549 (13) | 0.46726 (14) | 0.0158 (3) | |
H6A1 | −0.0273 | 0.3571 | 0.5294 | 0.019* | |
H6A2 | 0.2765 | 0.3863 | 0.4888 | 0.019* | |
C7A | 0.1170 (4) | 0.24156 (12) | 0.23793 (13) | 0.0141 (3) | |
H7A1 | −0.0637 | 0.2748 | 0.2045 | 0.017* | |
H7A2 | 0.2668 | 0.2424 | 0.1905 | 0.017* | |
O1B | 0.3880 (3) | 0.25805 (10) | 0.74236 (10) | 0.0137 (2) | |
H1OB | 0.3329 | 0.2915 | 0.7879 | 0.021* | |
O2B | 0.6121 (3) | 0.16627 (9) | 0.92550 (10) | 0.0132 (2) | |
O3B | 0.7254 (4) | 0.04529 (10) | 0.69129 (10) | 0.0150 (2) | |
H3OB | 0.6192 | 0.0715 | 0.6418 | 0.023* | |
O4B | 0.4371 (3) | −0.09378 (10) | 0.80479 (10) | 0.0150 (2) | |
H4OB | 0.3624 | −0.0791 | 0.7449 | 0.023* | |
O5B | 0.8761 (3) | 0.03990 (9) | 1.00595 (10) | 0.0133 (2) | |
O6B | 0.7253 (3) | −0.11157 (10) | 1.11773 (10) | 0.0145 (2) | |
H6OB | 0.5800 | −0.0811 | 1.1331 | 0.022* | |
C1B | 0.6997 (4) | 0.23627 (12) | 0.76962 (13) | 0.0127 (2) | |
H1B1 | 0.8038 | 0.2891 | 0.8071 | 0.015* | |
H1B2 | 0.7888 | 0.2268 | 0.7065 | 0.015* | |
C2B | 0.7496 (4) | 0.14990 (12) | 0.83586 (12) | 0.0112 (2) | |
H2B | 0.9696 | 0.1392 | 0.8564 | 0.013* | |
C3B | 0.6035 (4) | 0.06329 (11) | 0.78339 (12) | 0.0109 (2) | |
H3B | 0.3826 | 0.0739 | 0.7656 | 0.013* | |
C4B | 0.6567 (4) | −0.02684 (11) | 0.84480 (12) | 0.0112 (2) | |
H4B | 0.8588 | −0.0513 | 0.8363 | 0.013* | |
C5B | 0.6416 (4) | −0.02101 (12) | 0.95941 (12) | 0.0110 (2) | |
H5B | 0.4409 | 0.0023 | 0.9711 | 0.013* | |
C6B | 0.7051 (5) | −0.11558 (13) | 1.00924 (13) | 0.0147 (3) | |
H6B1 | 0.5430 | −0.1589 | 0.9815 | 0.018* | |
H6B2 | 0.8960 | −0.1399 | 0.9916 | 0.018* | |
C7B | 0.7811 (5) | 0.13247 (13) | 1.01596 (13) | 0.0161 (3) | |
H7B1 | 0.6586 | 0.1359 | 1.0719 | 0.019* | |
H7B2 | 0.9595 | 0.1723 | 1.0349 | 0.019* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0190 (5) | 0.0185 (6) | 0.0107 (4) | 0.0049 (5) | 0.0003 (4) | −0.0032 (4) |
O2A | 0.0156 (5) | 0.0098 (4) | 0.0096 (4) | 0.0008 (4) | −0.0019 (4) | 0.0003 (3) |
O3A | 0.0194 (5) | 0.0155 (5) | 0.0120 (5) | 0.0002 (5) | −0.0011 (4) | 0.0056 (4) |
O4A | 0.0252 (7) | 0.0227 (7) | 0.0084 (4) | −0.0094 (5) | 0.0055 (4) | −0.0030 (4) |
O5A | 0.0183 (5) | 0.0114 (5) | 0.0092 (4) | −0.0032 (4) | 0.0030 (4) | −0.0015 (4) |
O6A | 0.0223 (6) | 0.0122 (5) | 0.0173 (5) | −0.0001 (5) | 0.0044 (5) | −0.0027 (4) |
C1A | 0.0213 (7) | 0.0113 (6) | 0.0117 (6) | 0.0021 (5) | 0.0011 (5) | −0.0008 (5) |
C2A | 0.0137 (5) | 0.0105 (5) | 0.0088 (5) | 0.0013 (4) | −0.0002 (4) | 0.0005 (4) |
C3A | 0.0138 (5) | 0.0109 (5) | 0.0084 (5) | −0.0012 (5) | −0.0007 (4) | 0.0017 (4) |
C4A | 0.0158 (6) | 0.0122 (6) | 0.0078 (5) | −0.0029 (5) | 0.0022 (4) | −0.0004 (4) |
C5A | 0.0153 (6) | 0.0108 (5) | 0.0091 (5) | −0.0015 (5) | 0.0026 (4) | −0.0016 (4) |
C6A | 0.0222 (7) | 0.0130 (6) | 0.0122 (6) | −0.0012 (6) | 0.0022 (5) | −0.0048 (5) |
C7A | 0.0221 (7) | 0.0107 (6) | 0.0091 (5) | 0.0000 (5) | 0.0014 (5) | 0.0003 (4) |
O1B | 0.0158 (5) | 0.0138 (5) | 0.0107 (4) | 0.0032 (4) | −0.0008 (4) | −0.0022 (4) |
O2B | 0.0190 (5) | 0.0121 (5) | 0.0085 (4) | 0.0028 (4) | 0.0020 (4) | −0.0006 (4) |
O3B | 0.0248 (6) | 0.0133 (5) | 0.0076 (4) | 0.0014 (5) | 0.0042 (4) | 0.0003 (4) |
O4B | 0.0214 (6) | 0.0126 (5) | 0.0104 (4) | −0.0043 (4) | 0.0004 (4) | −0.0009 (4) |
O5B | 0.0173 (5) | 0.0101 (4) | 0.0110 (4) | 0.0000 (4) | −0.0025 (4) | −0.0002 (4) |
O6B | 0.0200 (5) | 0.0140 (5) | 0.0097 (4) | 0.0042 (4) | 0.0026 (4) | 0.0034 (4) |
C1B | 0.0153 (6) | 0.0103 (5) | 0.0124 (5) | −0.0010 (5) | 0.0016 (5) | 0.0007 (5) |
C2B | 0.0141 (5) | 0.0106 (5) | 0.0088 (5) | −0.0001 (5) | 0.0009 (4) | 0.0002 (4) |
C3B | 0.0144 (6) | 0.0095 (5) | 0.0086 (5) | −0.0002 (4) | 0.0014 (4) | 0.0002 (4) |
C4B | 0.0152 (6) | 0.0094 (5) | 0.0086 (5) | −0.0001 (5) | 0.0009 (4) | 0.0002 (4) |
C5B | 0.0144 (5) | 0.0100 (5) | 0.0082 (5) | 0.0003 (4) | 0.0008 (4) | 0.0002 (4) |
C6B | 0.0241 (7) | 0.0106 (6) | 0.0096 (5) | 0.0010 (5) | 0.0034 (5) | 0.0007 (5) |
C7B | 0.0265 (8) | 0.0114 (6) | 0.0093 (5) | 0.0008 (6) | −0.0009 (5) | −0.0011 (5) |
Geometric parameters (Å, º) top
O1A—C1A | 1.428 (2) | O1B—C1B | 1.431 (2) |
O1A—H1OA | 0.8400 | O1B—H1OB | 0.8400 |
O2A—C7A | 1.407 (2) | O2B—C7B | 1.404 (2) |
O2A—C2A | 1.437 (2) | O2B—C2B | 1.440 (2) |
O3A—C3A | 1.427 (2) | O3B—C3B | 1.435 (2) |
O3A—H3OA | 0.8400 | O3B—H3OB | 0.8400 |
O4A—C4A | 1.423 (2) | O4B—C4B | 1.427 (2) |
O4A—H4OA | 0.8400 | O4B—H4OB | 0.8400 |
O5A—C7A | 1.410 (2) | O5B—C7B | 1.418 (2) |
O5A—C5A | 1.435 (2) | O5B—C5B | 1.440 (2) |
O6A—C6A | 1.432 (3) | O6B—C6B | 1.425 (2) |
O6A—H6OA | 0.8400 | O6B—H6OB | 0.8400 |
C1A—C2A | 1.516 (2) | C1B—C2B | 1.523 (2) |
C1A—H1A1 | 0.9900 | C1B—H1B1 | 0.9900 |
C1A—H1A2 | 0.9900 | C1B—H1B2 | 0.9900 |
C2A—C3A | 1.530 (2) | C2B—C3B | 1.531 (2) |
C2A—H2A | 1.0000 | C2B—H2B | 1.0000 |
C3A—C4A | 1.534 (2) | C3B—C4B | 1.535 (2) |
C3A—H3A | 1.0000 | C3B—H3B | 1.0000 |
C4A—C5A | 1.532 (2) | C4B—C5B | 1.531 (2) |
C4A—H4A | 1.0000 | C4B—H4B | 1.0000 |
C5A—C6A | 1.512 (2) | C5B—C6B | 1.526 (2) |
C5A—H5A | 1.0000 | C5B—H5B | 1.0000 |
C6A—H6A1 | 0.9900 | C6B—H6B1 | 0.9900 |
C6A—H6A2 | 0.9900 | C6B—H6B2 | 0.9900 |
C7A—H7A1 | 0.9900 | C7B—H7B1 | 0.9900 |
C7A—H7A2 | 0.9900 | C7B—H7B2 | 0.9900 |
| | | |
C1A—O1A—H1OA | 109.5 | C1B—O1B—H1OB | 109.5 |
C7A—O2A—C2A | 113.69 (14) | C7B—O2B—C2B | 113.49 (14) |
C3A—O3A—H3OA | 109.5 | C3B—O3B—H3OB | 109.5 |
C4A—O4A—H4OA | 109.5 | C4B—O4B—H4OB | 109.5 |
C7A—O5A—C5A | 113.69 (14) | C7B—O5B—C5B | 113.89 (14) |
C6A—O6A—H6OA | 109.5 | C6B—O6B—H6OB | 109.5 |
O1A—C1A—C2A | 110.41 (15) | O1B—C1B—C2B | 112.23 (14) |
O1A—C1A—H1A1 | 109.6 | O1B—C1B—H1B1 | 109.2 |
C2A—C1A—H1A1 | 109.6 | C2B—C1B—H1B1 | 109.2 |
O1A—C1A—H1A2 | 109.6 | O1B—C1B—H1B2 | 109.2 |
C2A—C1A—H1A2 | 109.6 | C2B—C1B—H1B2 | 109.2 |
H1A1—C1A—H1A2 | 108.1 | H1B1—C1B—H1B2 | 107.9 |
O2A—C2A—C1A | 106.83 (13) | O2B—C2B—C1B | 107.15 (14) |
O2A—C2A—C3A | 107.98 (13) | O2B—C2B—C3B | 107.36 (14) |
C1A—C2A—C3A | 111.29 (14) | C1B—C2B—C3B | 113.25 (13) |
O2A—C2A—H2A | 110.2 | O2B—C2B—H2B | 109.7 |
C1A—C2A—H2A | 110.2 | C1B—C2B—H2B | 109.7 |
C3A—C2A—H2A | 110.2 | C3B—C2B—H2B | 109.7 |
O3A—C3A—C2A | 108.76 (14) | O3B—C3B—C2B | 109.83 (14) |
O3A—C3A—C4A | 108.18 (13) | O3B—C3B—C4B | 104.26 (13) |
C2A—C3A—C4A | 115.91 (13) | C2B—C3B—C4B | 115.67 (13) |
O3A—C3A—H3A | 107.9 | O3B—C3B—H3B | 109.0 |
C2A—C3A—H3A | 107.9 | C2B—C3B—H3B | 109.0 |
C4A—C3A—H3A | 107.9 | C4B—C3B—H3B | 109.0 |
O4A—C4A—C5A | 110.20 (15) | O4B—C4B—C5B | 105.72 (13) |
O4A—C4A—C3A | 105.79 (14) | O4B—C4B—C3B | 109.66 (13) |
C5A—C4A—C3A | 114.55 (13) | C5B—C4B—C3B | 116.77 (14) |
O4A—C4A—H4A | 108.7 | O4B—C4B—H4B | 108.1 |
C5A—C4A—H4A | 108.7 | C5B—C4B—H4B | 108.1 |
C3A—C4A—H4A | 108.7 | C3B—C4B—H4B | 108.1 |
O5A—C5A—C6A | 106.99 (14) | O5B—C5B—C6B | 106.66 (13) |
O5A—C5A—C4A | 108.10 (14) | O5B—C5B—C4B | 108.43 (13) |
C6A—C5A—C4A | 112.06 (14) | C6B—C5B—C4B | 110.17 (13) |
O5A—C5A—H5A | 109.9 | O5B—C5B—H5B | 110.5 |
C6A—C5A—H5A | 109.9 | C6B—C5B—H5B | 110.5 |
C4A—C5A—H5A | 109.9 | C4B—C5B—H5B | 110.5 |
O6A—C6A—C5A | 110.32 (14) | O6B—C6B—C5B | 112.17 (14) |
O6A—C6A—H6A1 | 109.6 | O6B—C6B—H6B1 | 109.2 |
C5A—C6A—H6A1 | 109.6 | C5B—C6B—H6B1 | 109.2 |
O6A—C6A—H6A2 | 109.6 | O6B—C6B—H6B2 | 109.2 |
C5A—C6A—H6A2 | 109.6 | C5B—C6B—H6B2 | 109.2 |
H6A1—C6A—H6A2 | 108.1 | H6B1—C6B—H6B2 | 107.9 |
O2A—C7A—O5A | 112.64 (14) | O2B—C7B—O5B | 112.41 (14) |
O2A—C7A—H7A1 | 109.1 | O2B—C7B—H7B1 | 109.1 |
O5A—C7A—H7A1 | 109.1 | O5B—C7B—H7B1 | 109.1 |
O2A—C7A—H7A2 | 109.1 | O2B—C7B—H7B2 | 109.1 |
O5A—C7A—H7A2 | 109.1 | O5B—C7B—H7B2 | 109.1 |
H7A1—C7A—H7A2 | 107.8 | H7B1—C7B—H7B2 | 107.9 |
| | | |
C7A—O2A—C2A—C1A | −143.63 (14) | C7B—O2B—C2B—C1B | −140.02 (15) |
C7A—O2A—C2A—C3A | 96.57 (16) | C7B—O2B—C2B—C3B | 98.03 (16) |
O1A—C1A—C2A—O2A | 60.42 (19) | O1B—C1B—C2B—O2B | −57.86 (18) |
O1A—C1A—C2A—C3A | 178.07 (15) | O1B—C1B—C2B—C3B | 60.33 (19) |
O2A—C2A—C3A—O3A | 172.90 (14) | O2B—C2B—C3B—O3B | 178.09 (13) |
C1A—C2A—C3A—O3A | 55.95 (18) | C1B—C2B—C3B—O3B | 60.03 (18) |
O2A—C2A—C3A—C4A | −65.01 (18) | O2B—C2B—C3B—C4B | −64.27 (18) |
C1A—C2A—C3A—C4A | 178.04 (15) | C1B—C2B—C3B—C4B | 177.66 (14) |
O3A—C3A—C4A—O4A | −72.18 (17) | O3B—C3B—C4B—O4B | −78.21 (16) |
C2A—C3A—C4A—O4A | 165.42 (14) | C2B—C3B—C4B—O4B | 161.09 (14) |
O3A—C3A—C4A—C5A | 166.25 (14) | O3B—C3B—C4B—C5B | 161.63 (14) |
C2A—C3A—C4A—C5A | 43.8 (2) | C2B—C3B—C4B—C5B | 40.9 (2) |
C7A—O5A—C5A—C6A | −142.15 (15) | C7B—O5B—C5B—C6B | −146.33 (14) |
C7A—O5A—C5A—C4A | 96.99 (16) | C7B—O5B—C5B—C4B | 95.05 (16) |
O4A—C4A—C5A—O5A | 174.36 (13) | O4B—C4B—C5B—O5B | 175.23 (13) |
C3A—C4A—C5A—O5A | −66.51 (18) | C3B—C4B—C5B—O5B | −62.54 (18) |
O4A—C4A—C5A—C6A | 56.70 (19) | O4B—C4B—C5B—C6B | 58.85 (18) |
C3A—C4A—C5A—C6A | 175.83 (15) | C3B—C4B—C5B—C6B | −178.91 (15) |
O5A—C5A—C6A—O6A | 65.76 (19) | O5B—C5B—C6B—O6B | 56.26 (19) |
C4A—C5A—C6A—O6A | −175.92 (15) | C4B—C5B—C6B—O6B | 173.73 (15) |
C2A—O2A—C7A—O5A | −48.8 (2) | C2B—O2B—C7B—O5B | −48.8 (2) |
C5A—O5A—C7A—O2A | −46.1 (2) | C5B—O5B—C7B—O2B | −47.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O5Bi | 0.84 | 2.02 | 2.8110 (19) | 156 |
O1A—H1OA···O6Bi | 0.84 | 2.54 | 3.109 (2) | 126 |
O3A—H3OA···O6Aii | 0.84 | 1.82 | 2.661 (2) | 177 |
O4A—H4OA···O1B | 0.84 | 1.88 | 2.7187 (19) | 173 |
O6A—H6OA···O3Biii | 0.84 | 1.92 | 2.745 (2) | 168 |
O1B—H1OB···O6Biv | 0.84 | 1.92 | 2.7447 (19) | 166 |
O3B—H3OB···O3A | 0.84 | 2.12 | 2.8111 (19) | 140 |
O4B—H4OB···O6Aii | 0.84 | 2.14 | 2.967 (2) | 166 |
O6B—H6OB···O1Av | 0.84 | 1.82 | 2.646 (2) | 170 |
Symmetry codes: (i) x−1, y, z−1; (ii) −x, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y+1/2, −z+2; (v) x, y, z+1. |
(II) 4(
R),7(
R)-di-(hydroxymethyl)-5(
R),6(
R)-dihydroxy-1,3-dioxepane
top
Crystal data top
C7H14O6 | F(000) = 416 |
Mr = 194.18 | Dx = 1.484 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.218 (3) Å | Cell parameters from 25 reflections |
b = 14.042 (7) Å | θ = 9.0–12.7° |
c = 9.160 (2) Å | µ = 0.13 mm−1 |
β = 110.64 (2)° | T = 100 K |
V = 868.9 (6) Å3 | Prism, colorless |
Z = 4 | 0.23 × 0.18 × 0.15 mm |
Data collection top
Enraf-Nonius CAD4 (with Oxford Cryostream) diffractometer | θmax = 32.0°, θmin = 2.3° |
ω–2θ scans | h = 0→10 |
3107 measured reflections | k = 0→20 |
3107 independent reflections | l = −13→12 |
2660 reflections with I > 2σ(I) | 3 standard reflections every 60 min |
Rint = 0 | intensity decay: 2.0% |
Refinement top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0412P)2 + 0.4465P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.113 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.39 e Å−3 |
3107 reflections | Δρmin = −0.32 e Å−3 |
235 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.6136 (3) | 0.99994 (14) | 0.6980 (2) | 0.0188 (4) | |
H1OA | 0.734 | 0.9998 | 0.7544 | 0.028* | |
O2A | 0.8384 (3) | 0.83075 (14) | 0.7446 (2) | 0.0141 (3) | |
O3A | 0.3412 (3) | 0.74000 (14) | 0.5579 (2) | 0.0149 (4) | |
H3OA | 0.2879 | 0.6889 | 0.5703 | 0.022* | |
O4A | 0.5664 (3) | 0.56767 (13) | 0.5909 (2) | 0.0140 (4) | |
H4OA | 0.5015 | 0.5406 | 0.5065 | 0.021* | |
O5A | 0.9216 (3) | 0.74394 (14) | 0.5582 (2) | 0.0136 (3) | |
O6A | 1.1450 (3) | 0.58171 (15) | 0.5790 (3) | 0.0267 (5) | |
H6OA | 1.1972 | 0.53 | 0.6191 | 0.04* | |
C1A | 0.5319 (4) | 0.9077 (2) | 0.6998 (3) | 0.0166 (5) | |
H1A1 | 0.3894 | 0.9083 | 0.635 | 0.02* | |
H1A2 | 0.5442 | 0.8913 | 0.8079 | 0.02* | |
C2A | 0.6365 (3) | 0.83316 (18) | 0.6380 (3) | 0.0114 (4) | |
H2A | 0.6322 | 0.851 | 0.5311 | 0.014* | |
C3A | 0.5498 (3) | 0.73377 (18) | 0.6359 (3) | 0.0113 (4) | |
H3A | 0.5758 | 0.7139 | 0.7461 | 0.014* | |
C4A | 0.6361 (3) | 0.65799 (17) | 0.5586 (3) | 0.0099 (4) | |
H4A | 0.5822 | 0.6686 | 0.4433 | 0.012* | |
C5A | 0.8634 (3) | 0.65711 (18) | 0.6128 (3) | 0.0119 (4) | |
H5A | 0.9227 | 0.653 | 0.7291 | 0.014* | |
C6A | 0.9355 (4) | 0.5755 (2) | 0.5377 (3) | 0.0176 (5) | |
H6A1 | 0.9002 | 0.514 | 0.5737 | 0.021* | |
H6A2 | 0.8707 | 0.5787 | 0.4229 | 0.021* | |
C7A | 0.9780 (4) | 0.81657 (19) | 0.6707 (3) | 0.0146 (5) | |
H7A1 | 0.9943 | 0.8767 | 0.6201 | 0.017* | |
H7A2 | 1.1076 | 0.8002 | 0.7505 | 0.017* | |
O1B | 0.2900 (3) | 0.41091 (14) | 0.7041 (2) | 0.0157 (4) | |
H1OB | 0.2065 | 0.3669 | 0.6887 | 0.024* | |
O2B | 0.4974 (3) | 0.25127 (14) | 0.8635 (2) | 0.0164 (4) | |
O3B | 0.7858 (3) | 0.46133 (13) | 0.8393 (2) | 0.0177 (4) | |
H3OB | 0.7281 | 0.4958 | 0.7616 | 0.026* | |
O4B | 0.9638 (3) | 0.31511 (14) | 0.7091 (2) | 0.0156 (4) | |
H4OB | 0.8807 | 0.2934 | 0.6265 | 0.023* | |
O5B | 0.8096 (3) | 0.18285 (14) | 0.9920 (2) | 0.0152 (4) | |
O6B | 1.0068 (3) | 0.03766 (14) | 0.8684 (2) | 0.0199 (4) | |
H6OB | 1.0352 | 0.0147 | 0.9583 | 0.03* | |
C1B | 0.4089 (4) | 0.4144 (2) | 0.8657 (3) | 0.0181 (5) | |
H1B1 | 0.3265 | 0.3987 | 0.9289 | 0.022* | |
H1B2 | 0.4611 | 0.4797 | 0.8934 | 0.022* | |
C2B | 0.5809 (4) | 0.34439 (18) | 0.9034 (3) | 0.0131 (5) | |
H2B | 0.6613 | 0.3471 | 1.0173 | 0.016* | |
C3B | 0.7135 (4) | 0.36573 (18) | 0.8078 (3) | 0.0119 (4) | |
H3B | 0.6294 | 0.3617 | 0.6948 | 0.014* | |
C4B | 0.8928 (4) | 0.30147 (18) | 0.8350 (3) | 0.0122 (4) | |
H4B | 0.9989 | 0.3238 | 0.9325 | 0.015* | |
C5B | 0.8603 (4) | 0.19514 (18) | 0.8551 (3) | 0.0122 (4) | |
H5B | 0.7505 | 0.1708 | 0.7616 | 0.015* | |
C6B | 1.0473 (4) | 0.13750 (19) | 0.8796 (3) | 0.0162 (5) | |
H6B1 | 1.1045 | 0.1559 | 0.8001 | 0.019* | |
H6B2 | 1.146 | 0.1521 | 0.9837 | 0.019* | |
C7B | 0.6048 (4) | 0.1779 (2) | 0.9622 (3) | 0.0183 (5) | |
H7B1 | 0.5818 | 0.1813 | 1.0624 | 0.022* | |
H7B2 | 0.5544 | 0.1156 | 0.9136 | 0.022* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0169 (9) | 0.0105 (8) | 0.0247 (10) | −0.0003 (7) | 0.0020 (7) | −0.0014 (8) |
O2A | 0.0108 (8) | 0.0150 (9) | 0.0139 (8) | −0.0008 (7) | 0.0010 (6) | −0.0007 (7) |
O3A | 0.0080 (7) | 0.0118 (8) | 0.0234 (9) | −0.0006 (7) | 0.0036 (7) | 0.0044 (7) |
O4A | 0.0119 (8) | 0.0096 (8) | 0.0206 (9) | −0.0032 (7) | 0.0058 (7) | 0.0004 (7) |
O5A | 0.0128 (8) | 0.0103 (8) | 0.0189 (8) | −0.0027 (7) | 0.0071 (7) | 0.0007 (7) |
O6A | 0.0113 (9) | 0.0140 (10) | 0.0574 (15) | 0.0037 (8) | 0.0154 (9) | 0.0088 (10) |
C1A | 0.0173 (12) | 0.0130 (11) | 0.0204 (12) | 0.0015 (10) | 0.0076 (10) | −0.0015 (10) |
C2A | 0.0105 (10) | 0.0098 (10) | 0.0119 (9) | −0.0007 (8) | 0.0016 (8) | 0.0004 (8) |
C3A | 0.0089 (10) | 0.0118 (11) | 0.0129 (10) | −0.0004 (8) | 0.0036 (8) | 0.0012 (8) |
C4A | 0.0079 (9) | 0.0087 (10) | 0.0131 (10) | −0.0024 (8) | 0.0038 (8) | −0.0002 (8) |
C5A | 0.0076 (9) | 0.0111 (11) | 0.0163 (10) | −0.0016 (8) | 0.0032 (8) | 0.0032 (9) |
C6A | 0.0127 (11) | 0.0139 (12) | 0.0280 (13) | −0.0008 (9) | 0.0093 (10) | −0.0006 (10) |
C7A | 0.0109 (10) | 0.0117 (11) | 0.0203 (11) | −0.0013 (9) | 0.0045 (9) | 0.0004 (9) |
O1B | 0.0127 (8) | 0.0147 (9) | 0.0184 (8) | −0.0006 (7) | 0.0038 (7) | 0.0024 (7) |
O2B | 0.0140 (8) | 0.0130 (8) | 0.0209 (9) | −0.0027 (7) | 0.0048 (7) | 0.0015 (7) |
O3B | 0.0194 (9) | 0.0105 (9) | 0.0185 (9) | −0.0008 (7) | 0.0009 (7) | 0.0015 (7) |
O4B | 0.0169 (9) | 0.0173 (9) | 0.0147 (8) | −0.0047 (7) | 0.0084 (7) | −0.0016 (7) |
O5B | 0.0158 (8) | 0.0154 (9) | 0.0154 (8) | 0.0003 (7) | 0.0067 (7) | 0.0022 (7) |
O6B | 0.0235 (10) | 0.0111 (9) | 0.0204 (9) | 0.0018 (8) | 0.0020 (8) | −0.0001 (7) |
C1B | 0.0154 (12) | 0.0191 (13) | 0.0187 (11) | 0.0040 (10) | 0.0045 (9) | −0.0032 (10) |
C2B | 0.0127 (11) | 0.0115 (11) | 0.0146 (10) | 0.0004 (9) | 0.0041 (8) | −0.0028 (9) |
C3B | 0.0124 (10) | 0.0095 (10) | 0.0120 (10) | −0.0013 (9) | 0.0022 (8) | 0.0000 (8) |
C4B | 0.0119 (10) | 0.0115 (11) | 0.0136 (10) | −0.0022 (9) | 0.0050 (8) | −0.0004 (8) |
C5B | 0.0135 (10) | 0.0101 (10) | 0.0146 (10) | −0.0027 (9) | 0.0070 (8) | −0.0012 (8) |
C6B | 0.0117 (10) | 0.0132 (12) | 0.0217 (12) | 0.0002 (9) | 0.0034 (9) | −0.0010 (10) |
C7B | 0.0175 (12) | 0.0170 (13) | 0.0228 (12) | −0.0009 (10) | 0.0101 (10) | 0.0057 (10) |
Geometric parameters (Å, º) top
O1A—C1A | 1.425 (3) | O1B—C1B | 1.426 (3) |
O1A—H1OA | 0.84 | O1B—H1OB | 0.84 |
O2A—C7A | 1.412 (3) | O2B—C7B | 1.409 (3) |
O2A—C2A | 1.440 (3) | O2B—C2B | 1.432 (3) |
O3A—C3A | 1.424 (3) | O3B—C3B | 1.432 (3) |
O3A—H3OA | 0.84 | O3B—H3OB | 0.84 |
O4A—C4A | 1.433 (3) | O4B—C4B | 1.430 (3) |
O4A—H4OA | 0.84 | O4B—H4OB | 0.84 |
O5A—C7A | 1.404 (3) | O5B—C7B | 1.407 (3) |
O5A—C5A | 1.436 (3) | O5B—C5B | 1.435 (3) |
O6A—C6A | 1.427 (3) | O6B—C6B | 1.428 (3) |
O6A—H6OA | 0.84 | O6B—H6OB | 0.84 |
C1A—C2A | 1.513 (4) | C1B—C2B | 1.525 (4) |
C1A—H1A1 | 0.99 | C1B—H1B1 | 0.99 |
C1A—H1A2 | 0.99 | C1B—H1B2 | 0.99 |
C2A—C3A | 1.527 (3) | C2B—C3B | 1.537 (4) |
C2A—H2A | 1.00 | C2B—H2B | 1.00 |
C3A—C4A | 1.527 (3) | C3B—C4B | 1.525 (4) |
C3A—H3A | 1.00 | C3B—H3B | 1.00 |
C4A—C5A | 1.538 (3) | C4B—C5B | 1.533 (3) |
C4A—H4A | 1.00 | C4B—H4B | 1.00 |
C5A—C6A | 1.519 (4) | C5B—C6B | 1.521 (4) |
C5A—H5A | 1.00 | C5B—H5B | 1.00 |
C6A—H6A1 | 0.99 | C6B—H6B1 | 0.99 |
C6A—H6A2 | 0.99 | C6B—H6B2 | 0.99 |
C7A—H7A1 | 0.99 | C7B—H7B1 | 0.99 |
C7A—H7A2 | 0.99 | C7B—H7B2 | 0.99 |
| | | |
C1A—O1A—H1OA | 109.5 | C1B—O1B—H1OB | 109.5 |
C7A—O2A—C2A | 113.60 (18) | C7B—O2B—C2B | 114.7 (2) |
C3A—O3A—H3OA | 109.5 | C3B—O3B—H3OB | 109.5 |
C4A—O4A—H4OA | 109.5 | C4B—O4B—H4OB | 109.5 |
C7A—O5A—C5A | 113.94 (19) | C7B—O5B—C5B | 114.20 (19) |
C6A—O6A—H6OA | 109.5 | C6B—O6B—H6OB | 109.5 |
O1A—C1A—C2A | 111.2 (2) | O1B—C1B—C2B | 110.9 (2) |
O1A—C1A—H1A1 | 109.4 | O1B—C1B—H1B1 | 109.5 |
C2A—C1A—H1A1 | 109.4 | C2B—C1B—H1B1 | 109.5 |
O1A—C1A—H1A2 | 109.4 | O1B—C1B—H1B2 | 109.5 |
C2A—C1A—H1A2 | 109.4 | C2B—C1B—H1B2 | 109.5 |
H1A1—C1A—H1A2 | 108.0 | H1B1—C1B—H1B2 | 108.0 |
O2A—C2A—C1A | 106.35 (19) | O2B—C2B—C1B | 107.2 (2) |
O2A—C2A—C3A | 107.41 (19) | O2B—C2B—C3B | 108.86 (19) |
C1A—C2A—C3A | 112.4 (2) | C1B—C2B—C3B | 111.5 (2) |
O2A—C2A—H2A | 110.2 | O2B—C2B—H2B | 109.8 |
C1A—C2A—H2A | 110.2 | C1B—C2B—H2B | 109.8 |
C3A—C2A—H2A | 110.2 | C3B—C2B—H2B | 109.8 |
O3A—C3A—C2A | 107.86 (19) | O3B—C3B—C4B | 107.1 (2) |
O3A—C3A—C4A | 110.03 (19) | O3B—C3B—C2B | 108.9 (2) |
C2A—C3A—C4A | 114.24 (19) | C4B—C3B—C2B | 117.1 (2) |
O3A—C3A—H3A | 108.2 | O3B—C3B—H3B | 107.8 |
C2A—C3A—H3A | 108.2 | C4B—C3B—H3B | 107.8 |
C4A—C3A—H3A | 108.2 | C2B—C3B—H3B | 107.8 |
O4A—C4A—C3A | 106.92 (18) | O4B—C4B—C3B | 108.3 (2) |
O4A—C4A—C5A | 109.79 (19) | O4B—C4B—C5B | 110.0 (2) |
C3A—C4A—C5A | 114.77 (19) | C3B—C4B—C5B | 116.0 (2) |
O4A—C4A—H4A | 108.4 | O4B—C4B—H4B | 107.4 |
C3A—C4A—H4A | 108.4 | C3B—C4B—H4B | 107.4 |
C5A—C4A—H4A | 108.4 | C5B—C4B—H4B | 107.4 |
O5A—C5A—C6A | 107.1 (2) | O5B—C5B—C6B | 107.1 (2) |
O5A—C5A—C4A | 106.90 (19) | O5B—C5B—C4B | 108.63 (19) |
C6A—C5A—C4A | 110.9 (2) | C6B—C5B—C4B | 111.7 (2) |
O5A—C5A—H5A | 110.6 | O5B—C5B—H5B | 109.8 |
C6A—C5A—H5A | 110.6 | C6B—C5B—H5B | 109.8 |
C4A—C5A—H5A | 110.6 | C4B—C5B—H5B | 109.8 |
O6A—C6A—C5A | 109.5 (2) | O6B—C6B—C5B | 111.3 (2) |
O6A—C6A—H6A1 | 109.8 | O6B—C6B—H6B1 | 109.4 |
C5A—C6A—H6A1 | 109.8 | C5B—C6B—H6B1 | 109.4 |
O6A—C6A—H6A2 | 109.8 | O6B—C6B—H6B2 | 109.4 |
C5A—C6A—H6A2 | 109.8 | C5B—C6B—H6B2 | 109.4 |
H6A1—C6A—H6A2 | 108.2 | H6B1—C6B—H6B2 | 108.0 |
O5A—C7A—O2A | 112.5 (2) | O5B—C7B—O2B | 113.0 (2) |
O5A—C7A—H7A1 | 109.1 | O5B—C7B—H7B1 | 109.0 |
O2A—C7A—H7A1 | 109.1 | O2B—C7B—H7B1 | 109.0 |
O5A—C7A—H7A2 | 109.1 | O5B—C7B—H7B2 | 109.0 |
O2A—C7A—H7A2 | 109.1 | O2B—C7B—H7B2 | 109.0 |
H7A1—C7A—H7A2 | 107.8 | H7B1—C7B—H7B2 | 107.8 |
| | | |
C7A—O2A—C2A—C1A | −142.6 (2) | C7B—O2B—C2B—C1B | −145.2 (2) |
C7A—O2A—C2A—C3A | 96.8 (2) | C7B—O2B—C2B—C3B | 94.1 (2) |
O1A—C1A—C2A—O2A | 63.7 (3) | O1B—C1B—C2B—O2B | −60.0 (3) |
O1A—C1A—C2A—C3A | −179.0 (2) | O1B—C1B—C2B—C3B | 59.0 (3) |
O2A—C2A—C3A—O3A | 167.88 (18) | O2B—C2B—C3B—O3B | 175.93 (19) |
C1A—C2A—C3A—O3A | 51.2 (3) | C1B—C2B—C3B—O3B | 57.9 (3) |
O2A—C2A—C3A—C4A | −69.5 (2) | O2B—C2B—C3B—C4B | −62.5 (3) |
C1A—C2A—C3A—C4A | 173.9 (2) | C1B—C2B—C3B—C4B | 179.5 (2) |
O3A—C3A—C4A—O4A | −68.6 (2) | O3B—C3B—C4B—O4B | −73.1 (2) |
C2A—C3A—C4A—O4A | 169.94 (18) | C2B—C3B—C4B—O4B | 164.4 (2) |
O3A—C3A—C4A—C5A | 169.39 (19) | O3B—C3B—C4B—C5B | 162.8 (2) |
C2A—C3A—C4A—C5A | 47.9 (3) | C2B—C3B—C4B—C5B | 40.3 (3) |
C7A—O5A—C5A—C6A | −143.6 (2) | C7B—O5B—C5B—C6B | −143.3 (2) |
C7A—O5A—C5A—C4A | 97.5 (2) | C7B—O5B—C5B—C4B | 95.9 (2) |
O4A—C4A—C5A—O5A | 172.23 (19) | O4B—C4B—C5B—O5B | 173.92 (19) |
C3A—C4A—C5A—O5A | −67.3 (3) | C3B—C4B—C5B—O5B | −62.8 (3) |
O4A—C4A—C5A—C6A | 55.9 (3) | O4B—C4B—C5B—C6B | 56.0 (3) |
C3A—C4A—C5A—C6A | 176.3 (2) | C3B—C4B—C5B—C6B | 179.3 (2) |
O5A—C5A—C6A—O6A | 58.5 (3) | O5B—C5B—C6B—O6B | 72.3 (3) |
C4A—C5A—C6A—O6A | 174.8 (2) | C4B—C5B—C6B—O6B | −168.9 (2) |
C5A—O5A—C7A—O2A | −49.5 (3) | C5B—O5B—C7B—O2B | −48.5 (3) |
C2A—O2A—C7A—O5A | −45.2 (3) | C2B—O2B—C7B—O5B | −46.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O6Bi | 0.84 | 1.95 | 2.765 (3) | 164 |
O3A—H3OA···O6Aii | 0.84 | 1.84 | 2.679 (3) | 173 |
O4A—H4OA···O1Aiii | 0.84 | 1.85 | 2.678 (3) | 167 |
O6A—H6OA···O1Biv | 0.84 | 1.87 | 2.705 (3) | 175 |
O1B—H1OB···O4Bii | 0.84 | 1.97 | 2.726 (3) | 150 |
O3B—H3OB···O4A | 0.84 | 1.88 | 2.716 (3) | 172 |
O4B—H4OB···O3Aiii | 0.84 | 2.02 | 2.854 (3) | 173 |
O6B—H6OB···O3Bv | 0.84 | 1.99 | 2.781 (3) | 156 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1; (iv) x+1, y, z; (v) −x+2, y−1/2, −z+2. |
(III) 4(
R),7(
R)-di-(hydroxymethyl)-5(
R),6(
R)-dihydroxy-1,3-dioxepane sodium iodide
top
Crystal data top
NaI·C7H14O6 | F(000) = 672 |
Mr = 344.07 | Dx = 1.876 Mg m−3 |
Orthorhombic, C2221 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2c 2 | Cell parameters from 25 reflections |
a = 6.948 (3) Å | θ = 22.0–31.3° |
b = 11.4543 (6) Å | µ = 2.67 mm−1 |
c = 15.3050 (7) Å | T = 297 K |
V = 1218.1 (5) Å3 | Prism, colorless |
Z = 4 | 0.38 × 0.32 × 0.20 mm |
Data collection top
Enraf Nonius CAD4 diffractometer | Rint = 0.019 |
ω–2θ scans | θmax = 40.0°, θmin = 2.7° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→12 |
Tmin = 0.430, Tmax = 0.598 | k = 0→20 |
3069 measured reflections | l = −21→27 |
2871 independent reflections | 3 standard reflections every 166 min |
2628 reflections with I > 2σ(I) | intensity decay: 1.0% |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0265P)2 + 0.4538P] where P = (Fo2 + 2Fc2)/3 |
Least-squares matrix: full | (Δ/σ)max = 0.001 |
R[F2 > 2σ(F2)] = 0.021 | Δρmax = 0.66 e Å−3 |
wR(F2) = 0.059 | Δρmin = −0.86 e Å−3 |
S = 1.09 | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2871 reflections | Extinction coefficient: 0.0144 (5) |
73 parameters | Absolute structure: Flack (1983), 758 Friedel pairs |
0 restraints | Absolute structure parameter: −0.025 (18) |
H-atom parameters constrained | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.5555 (2) | 0.14990 (15) | 0.64110 (13) | 0.0599 (4) | |
H1O | 0.4804 | 0.1124 | 0.6107 | 0.09* | |
O2 | 0.84362 (16) | 0.26345 (9) | 0.72186 (10) | 0.0380 (2) | |
O3 | 0.91871 (19) | −0.04362 (10) | 0.66643 (9) | 0.0403 (2) | |
H3O | 0.9995 | −0.0356 | 0.6279 | 0.06* | |
C1 | 0.7346 (3) | 0.16201 (17) | 0.59629 (13) | 0.0491 (4) | |
H1A | 0.7332 | 0.2319 | 0.5605 | 0.059* | |
H1B | 0.7559 | 0.0952 | 0.5585 | 0.059* | |
C2 | 0.8930 (2) | 0.16997 (13) | 0.66356 (11) | 0.0359 (3) | |
H2 | 1.0156 | 0.1872 | 0.6347 | 0.043* | |
C3 | 0.9130 (2) | 0.05947 (11) | 0.71928 (10) | 0.0325 (2) | |
H3 | 0.7976 | 0.0542 | 0.7559 | 0.039* | |
C7 | 1 | 0.33228 (18) | 0.75 | 0.0431 (5) | |
H7 | 0.9584 | 0.3821 | 0.7976 | 0.052* | |
I | 0.74135 (2) | 0 | 1 | 0.04623 (6) | |
Na | 1 | −0.21442 (9) | 0.75 | 0.0396 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0386 (6) | 0.0671 (9) | 0.0741 (10) | 0.0018 (6) | −0.0123 (7) | −0.0269 (8) |
O2 | 0.0276 (4) | 0.0286 (4) | 0.0578 (7) | 0.0022 (3) | −0.0010 (5) | −0.0051 (4) |
O3 | 0.0467 (6) | 0.0284 (4) | 0.0456 (6) | −0.0005 (4) | 0.0055 (5) | −0.0062 (4) |
C1 | 0.0527 (10) | 0.0441 (8) | 0.0503 (8) | 0.0073 (8) | −0.0089 (8) | −0.0016 (6) |
C2 | 0.0340 (6) | 0.0286 (5) | 0.0452 (8) | 0.0039 (5) | 0.0023 (5) | 0.0005 (5) |
C3 | 0.0304 (6) | 0.0254 (5) | 0.0418 (7) | −0.0004 (4) | 0.0051 (5) | −0.0027 (5) |
C7 | 0.0306 (8) | 0.0243 (7) | 0.0746 (16) | 0 | −0.0058 (10) | 0 |
I | 0.04411 (8) | 0.05565 (10) | 0.03894 (8) | 0 | 0 | 0.00966 (6) |
Na | 0.0312 (4) | 0.0280 (4) | 0.0595 (6) | 0 | 0.0008 (4) | 0 |
Geometric parameters (Å, º) top
O1—C1 | 1.428 (3) | C2—H2 | 0.98 |
O1—H1O | 0.82 | C3—C3ii | 1.532 (3) |
O2—C7 | 1.4098 (15) | C3—H3 | 0.98 |
O2—C2 | 1.4354 (19) | C7—O2ii | 1.4098 (15) |
O2—Nai | 2.4393 (11) | C7—H7 | 0.97 |
O3—C3 | 1.4318 (17) | Na—O1iii | 2.3112 (17) |
O3—H3O | 0.82 | Na—O1iv | 2.3112 (17) |
C1—C2 | 1.510 (2) | Na—O2iii | 2.4393 (11) |
C1—H1A | 0.97 | Na—O2iv | 2.4393 (11) |
C1—H1B | 0.97 | Na—O3ii | 2.4047 (15) |
C2—C3 | 1.533 (2) | | |
| | | |
C1—O1—H1O | 109.5 | C3ii—C3—C2 | 114.41 (10) |
C7—O2—C2 | 115.02 (11) | O3—C3—H3 | 107.1 |
C7—O2—Nai | 129.96 (9) | C3ii—C3—H3 | 107.1 |
C2—O2—Nai | 114.91 (9) | C2—C3—H3 | 107.1 |
C3—O3—H3O | 109.5 | O2—C7—O2ii | 112.00 (16) |
O1—C1—C2 | 108.28 (16) | O2—C7—H7 | 109.2 |
O1—C1—H1A | 110.0 | O2ii—C7—H7 | 109.2 |
C2—C1—H1A | 110.0 | H7—C7—H7ii | 107.9 |
O1—C1—H1B | 110.0 | O1iii—Na—O1iv | 95.49 (11) |
C2—C1—H1B | 110.0 | O1iii—Na—O3ii | 153.05 (5) |
H1A—C1—H1B | 108.4 | O1iv—Na—O3ii | 101.69 (6) |
O2—C2—C1 | 107.15 (13) | O1iii—Na—O2iii | 68.87 (5) |
O2—C2—C3 | 106.97 (13) | O1iv—Na—O2iii | 102.75 (5) |
C1—C2—C3 | 113.31 (13) | O3ii—Na—O2iii | 87.05 (4) |
O2—C2—H2 | 109.8 | O1iii—Na—O2iv | 102.75 (5) |
C1—C2—H2 | 109.8 | O1iv—Na—O2iv | 68.87 (5) |
C3—C2—H2 | 109.8 | O3ii—Na—O2iv | 102.74 (5) |
O3—C3—C3ii | 108.97 (10) | O2iii—Na—O2iv | 168.07 (7) |
O3—C3—C2 | 111.67 (12) | | |
| | | |
C7—O2—C2—C1 | −141.66 (14) | C1—C2—C3—O3 | 48.90 (17) |
Nai—O2—C2—C1 | 34.89 (16) | O2—C2—C3—C3ii | −68.89 (17) |
C7—O2—C2—C3 | 96.52 (15) | C2—C3—C3ii—C2ii | 49.82 (17) |
Nai—O2—C2—C3 | −86.93 (12) | O3—C3—C3ii—O3ii | −58.61 (15) |
O1—C1—C2—O2 | −54.50 (18) | C1—C2—C3—C3ii | 173.26 (15) |
O1—C1—C2—C3 | 63.25 (18) | C2—O2—C7—O2ii | −47.30 (10) |
O2—C2—C3—O3 | 166.75 (12) | Nai—O2—C7—O2ii | 136.78 (14) |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+2, y, −z+3/2; (iii) x+1/2, y−1/2, z; (iv) −x+3/2, y−1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···Iv | 0.82 | 2.63 | 3.4447 (14) | 174 |
O3—H3O···Ivi | 0.82 | 2.69 | 3.5095 (13) | 177 |
Symmetry codes: (v) −x+1, −y, z−1/2; (vi) −x+2, −y, z−1/2. |
Torsion angles (°) in some 1,3-dioxepanes. aThis work;
bNaCl complex: Wood et al. (1976);
c1,3:2,5:4,6-tri-O-methylene-D-mannitol (Hanson, 1986);
d1,3,4,6-tetra-O-acetyl-2,5-O-methylene-D-mannitol
(Cameron et al., 1977) topAtoms | | 1Aa | 1Ba | 2Aa | 2Ba | NaIcmplxa | b | c | d |
C2/C3/C4/C5 | | 43.8 (2) | 40.9 (2) | 47.9 (3) | 40.3 (3) | 49.82 (17) | 47.5 (3) | 48.8 (6) | 45.1 (4) |
O2/C2/C3/C4 | | -65.01 (18) | -64.27 (18) | -69.5 (2) | -62.5 (3) | -68.89 (17) | -67.3 (2) | -69.6 (6) | -61.5 (4) |
C3/C4/C5/O5 | | -66.51 (18) | -62.54 (18) | -67.3 (3) | -62.8 (3) | -68.89 (17) | -67.3 (2) | -69.2 (6) | -69.9 (4) |
C7/O2/C2/C3 | | 96.57 (16) | 98.03 (16) | 96.8 (2) | 94.1 (2) | 96.52 (15) | 97.0 (2) | 97.1 (6) | 94.5 (4) |
C7/O5/C5/C4 | | 96.99 (16) | 95.05 (16) | 97.5 (2) | 95.9 (2) | 96.52 (15) | 97.0 (2) | 94.9 (6) | 98.5 (4) |
C2/O2/C7/O5 | | -48.8 (2) | -48.8 (2) | -45.2 (3) | -46.4 (3) | -47.30 (10) | -47.7 (2) | -47.6 (7) | -50.2 (4) |
C5/O5/C7/O2 | | -46.1 (2) | -47.3 (2) | -49.5 (3) | -48.5 (3) | -47.30 (10) | -47.7 (2) | -44.3 (7) | -45.6 (4) |
O1/C1/C2/O2 | | 60.42 (19) | -57.86 (18) | 63.7 (3) | -60.0 (3) | -54.50 (18) | -53.8 (2) | -173.1 (5) | 65.3 (4) |
O3/C3/C4/O4 | | -72.18 (7) | -78.21 (16) | -68.6 (2) | -73.1 (2) | -58.61 (15) | -61.0 (3) | -72.0 (5) | -72.4 (4) |
O5/C5/C6/O6 | | 65.76 (9) | 56.26 (19) | 58.5 (3) | 72.3 (3) | -54.50 (18) | -53.8 (2) | -172.0 (4) | 68.8 (4) |