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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000506/da1162sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000506/da1162Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000506/da1162IIsup3.hkl
Contains datablock form2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000506/da1162IIIsup4.hkl
Contains datablock NaIcmplx

CCDC references: 163890; 163891; 163892

Computing details top

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
C7H14O6F(000) = 416
Mr = 194.18Dx = 1.512 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 4.5100 (4) ÅCell parameters from 25 reflections
b = 14.462 (1) Åθ = 9.7–18.3°
c = 13.231 (1) ŵ = 0.13 mm1
β = 98.823 (7)°T = 100 K
V = 852.76 (12) Å3Needle fragment, colorless
Z = 40.37 × 0.35 × 0.25 mm
Data collection top
Enraf-Nonius CAD4 (with Oxford Cryostream)
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 45.0°, θmin = 2.8°
Graphite monochromatorh = 08
ω–2θ scansk = 028
7174 measured reflectionsl = 2625
7174 independent reflections3 standard reflections every 60 min
5701 reflections with I > 2σ(I) intensity decay: 5.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-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 reflectionsΔρmax = 0.70 e Å3
236 parametersΔρmin = 0.52 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O1A0.3164 (3)0.00009 (11)0.17474 (10)0.0163 (2)
H1OA0.15240.00460.13520.024*
O2A0.0397 (3)0.14935 (9)0.25554 (9)0.01210 (19)
O3A0.4104 (3)0.04236 (11)0.49076 (10)0.0160 (2)
H3OA0.31640.00800.52600.024*
O4A0.0748 (4)0.18711 (12)0.56764 (10)0.0185 (3)
H4OA0.18330.21050.61850.028*
O5A0.2358 (3)0.28832 (9)0.32870 (10)0.0129 (2)
O6A0.0941 (4)0.43415 (10)0.40284 (12)0.0171 (2)
H6OA0.02370.46110.36920.026*
C1A0.2625 (5)0.00079 (13)0.27831 (14)0.0149 (3)
H1A10.41670.03700.32100.018*
H1A20.06370.02680.28210.018*
C2A0.2717 (4)0.09886 (12)0.31908 (12)0.0112 (2)
H2A0.47190.12740.31570.013*
C3A0.2039 (4)0.10155 (12)0.42887 (12)0.0113 (2)
H3A0.00250.07620.42850.014*
C4A0.2174 (4)0.19724 (12)0.47948 (12)0.0119 (2)
H4A0.43240.21410.50200.014*
C5A0.0665 (4)0.27455 (12)0.41088 (12)0.0117 (2)
H5A0.14410.25650.38280.014*
C6A0.0671 (5)0.36549 (13)0.46726 (14)0.0158 (3)
H6A10.02730.35710.52940.019*
H6A20.27650.38630.48880.019*
C7A0.1170 (4)0.24156 (12)0.23793 (13)0.0141 (3)
H7A10.06370.27480.20450.017*
H7A20.26680.24240.19050.017*
O1B0.3880 (3)0.25805 (10)0.74236 (10)0.0137 (2)
H1OB0.33290.29150.78790.021*
O2B0.6121 (3)0.16627 (9)0.92550 (10)0.0132 (2)
O3B0.7254 (4)0.04529 (10)0.69129 (10)0.0150 (2)
H3OB0.61920.07150.64180.023*
O4B0.4371 (3)0.09378 (10)0.80479 (10)0.0150 (2)
H4OB0.36240.07910.74490.023*
O5B0.8761 (3)0.03990 (9)1.00595 (10)0.0133 (2)
O6B0.7253 (3)0.11157 (10)1.11773 (10)0.0145 (2)
H6OB0.58000.08111.13310.022*
C1B0.6997 (4)0.23627 (12)0.76962 (13)0.0127 (2)
H1B10.80380.28910.80710.015*
H1B20.78880.22680.70650.015*
C2B0.7496 (4)0.14990 (12)0.83586 (12)0.0112 (2)
H2B0.96960.13920.85640.013*
C3B0.6035 (4)0.06329 (11)0.78339 (12)0.0109 (2)
H3B0.38260.07390.76560.013*
C4B0.6567 (4)0.02684 (11)0.84480 (12)0.0112 (2)
H4B0.85880.05130.83630.013*
C5B0.6416 (4)0.02101 (12)0.95941 (12)0.0110 (2)
H5B0.44090.00230.97110.013*
C6B0.7051 (5)0.11558 (13)1.00924 (13)0.0147 (3)
H6B10.54300.15890.98150.018*
H6B20.89600.13990.99160.018*
C7B0.7811 (5)0.13247 (13)1.01596 (13)0.0161 (3)
H7B10.65860.13591.07190.019*
H7B20.95950.17231.03490.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0190 (5)0.0185 (6)0.0107 (4)0.0049 (5)0.0003 (4)0.0032 (4)
O2A0.0156 (5)0.0098 (4)0.0096 (4)0.0008 (4)0.0019 (4)0.0003 (3)
O3A0.0194 (5)0.0155 (5)0.0120 (5)0.0002 (5)0.0011 (4)0.0056 (4)
O4A0.0252 (7)0.0227 (7)0.0084 (4)0.0094 (5)0.0055 (4)0.0030 (4)
O5A0.0183 (5)0.0114 (5)0.0092 (4)0.0032 (4)0.0030 (4)0.0015 (4)
O6A0.0223 (6)0.0122 (5)0.0173 (5)0.0001 (5)0.0044 (5)0.0027 (4)
C1A0.0213 (7)0.0113 (6)0.0117 (6)0.0021 (5)0.0011 (5)0.0008 (5)
C2A0.0137 (5)0.0105 (5)0.0088 (5)0.0013 (4)0.0002 (4)0.0005 (4)
C3A0.0138 (5)0.0109 (5)0.0084 (5)0.0012 (5)0.0007 (4)0.0017 (4)
C4A0.0158 (6)0.0122 (6)0.0078 (5)0.0029 (5)0.0022 (4)0.0004 (4)
C5A0.0153 (6)0.0108 (5)0.0091 (5)0.0015 (5)0.0026 (4)0.0016 (4)
C6A0.0222 (7)0.0130 (6)0.0122 (6)0.0012 (6)0.0022 (5)0.0048 (5)
C7A0.0221 (7)0.0107 (6)0.0091 (5)0.0000 (5)0.0014 (5)0.0003 (4)
O1B0.0158 (5)0.0138 (5)0.0107 (4)0.0032 (4)0.0008 (4)0.0022 (4)
O2B0.0190 (5)0.0121 (5)0.0085 (4)0.0028 (4)0.0020 (4)0.0006 (4)
O3B0.0248 (6)0.0133 (5)0.0076 (4)0.0014 (5)0.0042 (4)0.0003 (4)
O4B0.0214 (6)0.0126 (5)0.0104 (4)0.0043 (4)0.0004 (4)0.0009 (4)
O5B0.0173 (5)0.0101 (4)0.0110 (4)0.0000 (4)0.0025 (4)0.0002 (4)
O6B0.0200 (5)0.0140 (5)0.0097 (4)0.0042 (4)0.0026 (4)0.0034 (4)
C1B0.0153 (6)0.0103 (5)0.0124 (5)0.0010 (5)0.0016 (5)0.0007 (5)
C2B0.0141 (5)0.0106 (5)0.0088 (5)0.0001 (5)0.0009 (4)0.0002 (4)
C3B0.0144 (6)0.0095 (5)0.0086 (5)0.0002 (4)0.0014 (4)0.0002 (4)
C4B0.0152 (6)0.0094 (5)0.0086 (5)0.0001 (5)0.0009 (4)0.0002 (4)
C5B0.0144 (5)0.0100 (5)0.0082 (5)0.0003 (4)0.0008 (4)0.0002 (4)
C6B0.0241 (7)0.0106 (6)0.0096 (5)0.0010 (5)0.0034 (5)0.0007 (5)
C7B0.0265 (8)0.0114 (6)0.0093 (5)0.0008 (6)0.0009 (5)0.0011 (5)
Geometric parameters (Å, º) top
O1A—C1A1.428 (2)O1B—C1B1.431 (2)
O1A—H1OA0.8400O1B—H1OB0.8400
O2A—C7A1.407 (2)O2B—C7B1.404 (2)
O2A—C2A1.437 (2)O2B—C2B1.440 (2)
O3A—C3A1.427 (2)O3B—C3B1.435 (2)
O3A—H3OA0.8400O3B—H3OB0.8400
O4A—C4A1.423 (2)O4B—C4B1.427 (2)
O4A—H4OA0.8400O4B—H4OB0.8400
O5A—C7A1.410 (2)O5B—C7B1.418 (2)
O5A—C5A1.435 (2)O5B—C5B1.440 (2)
O6A—C6A1.432 (3)O6B—C6B1.425 (2)
O6A—H6OA0.8400O6B—H6OB0.8400
C1A—C2A1.516 (2)C1B—C2B1.523 (2)
C1A—H1A10.9900C1B—H1B10.9900
C1A—H1A20.9900C1B—H1B20.9900
C2A—C3A1.530 (2)C2B—C3B1.531 (2)
C2A—H2A1.0000C2B—H2B1.0000
C3A—C4A1.534 (2)C3B—C4B1.535 (2)
C3A—H3A1.0000C3B—H3B1.0000
C4A—C5A1.532 (2)C4B—C5B1.531 (2)
C4A—H4A1.0000C4B—H4B1.0000
C5A—C6A1.512 (2)C5B—C6B1.526 (2)
C5A—H5A1.0000C5B—H5B1.0000
C6A—H6A10.9900C6B—H6B10.9900
C6A—H6A20.9900C6B—H6B20.9900
C7A—H7A10.9900C7B—H7B10.9900
C7A—H7A20.9900C7B—H7B20.9900
C1A—O1A—H1OA109.5C1B—O1B—H1OB109.5
C7A—O2A—C2A113.69 (14)C7B—O2B—C2B113.49 (14)
C3A—O3A—H3OA109.5C3B—O3B—H3OB109.5
C4A—O4A—H4OA109.5C4B—O4B—H4OB109.5
C7A—O5A—C5A113.69 (14)C7B—O5B—C5B113.89 (14)
C6A—O6A—H6OA109.5C6B—O6B—H6OB109.5
O1A—C1A—C2A110.41 (15)O1B—C1B—C2B112.23 (14)
O1A—C1A—H1A1109.6O1B—C1B—H1B1109.2
C2A—C1A—H1A1109.6C2B—C1B—H1B1109.2
O1A—C1A—H1A2109.6O1B—C1B—H1B2109.2
C2A—C1A—H1A2109.6C2B—C1B—H1B2109.2
H1A1—C1A—H1A2108.1H1B1—C1B—H1B2107.9
O2A—C2A—C1A106.83 (13)O2B—C2B—C1B107.15 (14)
O2A—C2A—C3A107.98 (13)O2B—C2B—C3B107.36 (14)
C1A—C2A—C3A111.29 (14)C1B—C2B—C3B113.25 (13)
O2A—C2A—H2A110.2O2B—C2B—H2B109.7
C1A—C2A—H2A110.2C1B—C2B—H2B109.7
C3A—C2A—H2A110.2C3B—C2B—H2B109.7
O3A—C3A—C2A108.76 (14)O3B—C3B—C2B109.83 (14)
O3A—C3A—C4A108.18 (13)O3B—C3B—C4B104.26 (13)
C2A—C3A—C4A115.91 (13)C2B—C3B—C4B115.67 (13)
O3A—C3A—H3A107.9O3B—C3B—H3B109.0
C2A—C3A—H3A107.9C2B—C3B—H3B109.0
C4A—C3A—H3A107.9C4B—C3B—H3B109.0
O4A—C4A—C5A110.20 (15)O4B—C4B—C5B105.72 (13)
O4A—C4A—C3A105.79 (14)O4B—C4B—C3B109.66 (13)
C5A—C4A—C3A114.55 (13)C5B—C4B—C3B116.77 (14)
O4A—C4A—H4A108.7O4B—C4B—H4B108.1
C5A—C4A—H4A108.7C5B—C4B—H4B108.1
C3A—C4A—H4A108.7C3B—C4B—H4B108.1
O5A—C5A—C6A106.99 (14)O5B—C5B—C6B106.66 (13)
O5A—C5A—C4A108.10 (14)O5B—C5B—C4B108.43 (13)
C6A—C5A—C4A112.06 (14)C6B—C5B—C4B110.17 (13)
O5A—C5A—H5A109.9O5B—C5B—H5B110.5
C6A—C5A—H5A109.9C6B—C5B—H5B110.5
C4A—C5A—H5A109.9C4B—C5B—H5B110.5
O6A—C6A—C5A110.32 (14)O6B—C6B—C5B112.17 (14)
O6A—C6A—H6A1109.6O6B—C6B—H6B1109.2
C5A—C6A—H6A1109.6C5B—C6B—H6B1109.2
O6A—C6A—H6A2109.6O6B—C6B—H6B2109.2
C5A—C6A—H6A2109.6C5B—C6B—H6B2109.2
H6A1—C6A—H6A2108.1H6B1—C6B—H6B2107.9
O2A—C7A—O5A112.64 (14)O2B—C7B—O5B112.41 (14)
O2A—C7A—H7A1109.1O2B—C7B—H7B1109.1
O5A—C7A—H7A1109.1O5B—C7B—H7B1109.1
O2A—C7A—H7A2109.1O2B—C7B—H7B2109.1
O5A—C7A—H7A2109.1O5B—C7B—H7B2109.1
H7A1—C7A—H7A2107.8H7B1—C7B—H7B2107.9
C7A—O2A—C2A—C1A143.63 (14)C7B—O2B—C2B—C1B140.02 (15)
C7A—O2A—C2A—C3A96.57 (16)C7B—O2B—C2B—C3B98.03 (16)
O1A—C1A—C2A—O2A60.42 (19)O1B—C1B—C2B—O2B57.86 (18)
O1A—C1A—C2A—C3A178.07 (15)O1B—C1B—C2B—C3B60.33 (19)
O2A—C2A—C3A—O3A172.90 (14)O2B—C2B—C3B—O3B178.09 (13)
C1A—C2A—C3A—O3A55.95 (18)C1B—C2B—C3B—O3B60.03 (18)
O2A—C2A—C3A—C4A65.01 (18)O2B—C2B—C3B—C4B64.27 (18)
C1A—C2A—C3A—C4A178.04 (15)C1B—C2B—C3B—C4B177.66 (14)
O3A—C3A—C4A—O4A72.18 (17)O3B—C3B—C4B—O4B78.21 (16)
C2A—C3A—C4A—O4A165.42 (14)C2B—C3B—C4B—O4B161.09 (14)
O3A—C3A—C4A—C5A166.25 (14)O3B—C3B—C4B—C5B161.63 (14)
C2A—C3A—C4A—C5A43.8 (2)C2B—C3B—C4B—C5B40.9 (2)
C7A—O5A—C5A—C6A142.15 (15)C7B—O5B—C5B—C6B146.33 (14)
C7A—O5A—C5A—C4A96.99 (16)C7B—O5B—C5B—C4B95.05 (16)
O4A—C4A—C5A—O5A174.36 (13)O4B—C4B—C5B—O5B175.23 (13)
C3A—C4A—C5A—O5A66.51 (18)C3B—C4B—C5B—O5B62.54 (18)
O4A—C4A—C5A—C6A56.70 (19)O4B—C4B—C5B—C6B58.85 (18)
C3A—C4A—C5A—C6A175.83 (15)C3B—C4B—C5B—C6B178.91 (15)
O5A—C5A—C6A—O6A65.76 (19)O5B—C5B—C6B—O6B56.26 (19)
C4A—C5A—C6A—O6A175.92 (15)C4B—C5B—C6B—O6B173.73 (15)
C2A—O2A—C7A—O5A48.8 (2)C2B—O2B—C7B—O5B48.8 (2)
C5A—O5A—C7A—O2A46.1 (2)C5B—O5B—C7B—O2B47.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O5Bi0.842.022.8110 (19)156
O1A—H1OA···O6Bi0.842.543.109 (2)126
O3A—H3OA···O6Aii0.841.822.661 (2)177
O4A—H4OA···O1B0.841.882.7187 (19)173
O6A—H6OA···O3Biii0.841.922.745 (2)168
O1B—H1OB···O6Biv0.841.922.7447 (19)166
O3B—H3OB···O3A0.842.122.8111 (19)140
O4B—H4OB···O6Aii0.842.142.967 (2)166
O6B—H6OB···O1Av0.841.822.646 (2)170
Symmetry codes: (i) x1, y, z1; (ii) x, y1/2, 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
C7H14O6F(000) = 416
Mr = 194.18Dx = 1.484 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.218 (3) ÅCell parameters from 25 reflections
b = 14.042 (7) Åθ = 9.0–12.7°
c = 9.160 (2) ŵ = 0.13 mm1
β = 110.64 (2)°T = 100 K
V = 868.9 (6) Å3Prism, colorless
Z = 40.23 × 0.18 × 0.15 mm
Data collection top
Enraf-Nonius CAD4 (with Oxford Cryostream)
diffractometer
θmax = 32.0°, θmin = 2.3°
ω–2θ scansh = 010
3107 measured reflectionsk = 020
3107 independent reflectionsl = 1312
2660 reflections with I > 2σ(I)3 standard reflections every 60 min
Rint = 0 intensity decay: 2.0%
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullH-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 = 1.07Δρmax = 0.39 e Å3
3107 reflectionsΔρmin = 0.32 e Å3
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
xyzUiso*/Ueq
O1A0.6136 (3)0.99994 (14)0.6980 (2)0.0188 (4)
H1OA0.7340.99980.75440.028*
O2A0.8384 (3)0.83075 (14)0.7446 (2)0.0141 (3)
O3A0.3412 (3)0.74000 (14)0.5579 (2)0.0149 (4)
H3OA0.28790.68890.57030.022*
O4A0.5664 (3)0.56767 (13)0.5909 (2)0.0140 (4)
H4OA0.50150.54060.50650.021*
O5A0.9216 (3)0.74394 (14)0.5582 (2)0.0136 (3)
O6A1.1450 (3)0.58171 (15)0.5790 (3)0.0267 (5)
H6OA1.19720.530.61910.04*
C1A0.5319 (4)0.9077 (2)0.6998 (3)0.0166 (5)
H1A10.38940.90830.6350.02*
H1A20.54420.89130.80790.02*
C2A0.6365 (3)0.83316 (18)0.6380 (3)0.0114 (4)
H2A0.63220.8510.53110.014*
C3A0.5498 (3)0.73377 (18)0.6359 (3)0.0113 (4)
H3A0.57580.71390.74610.014*
C4A0.6361 (3)0.65799 (17)0.5586 (3)0.0099 (4)
H4A0.58220.66860.44330.012*
C5A0.8634 (3)0.65711 (18)0.6128 (3)0.0119 (4)
H5A0.92270.6530.72910.014*
C6A0.9355 (4)0.5755 (2)0.5377 (3)0.0176 (5)
H6A10.90020.5140.57370.021*
H6A20.87070.57870.42290.021*
C7A0.9780 (4)0.81657 (19)0.6707 (3)0.0146 (5)
H7A10.99430.87670.62010.017*
H7A21.10760.80020.75050.017*
O1B0.2900 (3)0.41091 (14)0.7041 (2)0.0157 (4)
H1OB0.20650.36690.68870.024*
O2B0.4974 (3)0.25127 (14)0.8635 (2)0.0164 (4)
O3B0.7858 (3)0.46133 (13)0.8393 (2)0.0177 (4)
H3OB0.72810.49580.76160.026*
O4B0.9638 (3)0.31511 (14)0.7091 (2)0.0156 (4)
H4OB0.88070.29340.62650.023*
O5B0.8096 (3)0.18285 (14)0.9920 (2)0.0152 (4)
O6B1.0068 (3)0.03766 (14)0.8684 (2)0.0199 (4)
H6OB1.03520.01470.95830.03*
C1B0.4089 (4)0.4144 (2)0.8657 (3)0.0181 (5)
H1B10.32650.39870.92890.022*
H1B20.46110.47970.89340.022*
C2B0.5809 (4)0.34439 (18)0.9034 (3)0.0131 (5)
H2B0.66130.34711.01730.016*
C3B0.7135 (4)0.36573 (18)0.8078 (3)0.0119 (4)
H3B0.62940.36170.69480.014*
C4B0.8928 (4)0.30147 (18)0.8350 (3)0.0122 (4)
H4B0.99890.32380.93250.015*
C5B0.8603 (4)0.19514 (18)0.8551 (3)0.0122 (4)
H5B0.75050.17080.76160.015*
C6B1.0473 (4)0.13750 (19)0.8796 (3)0.0162 (5)
H6B11.10450.15590.80010.019*
H6B21.1460.15210.98370.019*
C7B0.6048 (4)0.1779 (2)0.9622 (3)0.0183 (5)
H7B10.58180.18131.06240.022*
H7B20.55440.11560.91360.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0169 (9)0.0105 (8)0.0247 (10)0.0003 (7)0.0020 (7)0.0014 (8)
O2A0.0108 (8)0.0150 (9)0.0139 (8)0.0008 (7)0.0010 (6)0.0007 (7)
O3A0.0080 (7)0.0118 (8)0.0234 (9)0.0006 (7)0.0036 (7)0.0044 (7)
O4A0.0119 (8)0.0096 (8)0.0206 (9)0.0032 (7)0.0058 (7)0.0004 (7)
O5A0.0128 (8)0.0103 (8)0.0189 (8)0.0027 (7)0.0071 (7)0.0007 (7)
O6A0.0113 (9)0.0140 (10)0.0574 (15)0.0037 (8)0.0154 (9)0.0088 (10)
C1A0.0173 (12)0.0130 (11)0.0204 (12)0.0015 (10)0.0076 (10)0.0015 (10)
C2A0.0105 (10)0.0098 (10)0.0119 (9)0.0007 (8)0.0016 (8)0.0004 (8)
C3A0.0089 (10)0.0118 (11)0.0129 (10)0.0004 (8)0.0036 (8)0.0012 (8)
C4A0.0079 (9)0.0087 (10)0.0131 (10)0.0024 (8)0.0038 (8)0.0002 (8)
C5A0.0076 (9)0.0111 (11)0.0163 (10)0.0016 (8)0.0032 (8)0.0032 (9)
C6A0.0127 (11)0.0139 (12)0.0280 (13)0.0008 (9)0.0093 (10)0.0006 (10)
C7A0.0109 (10)0.0117 (11)0.0203 (11)0.0013 (9)0.0045 (9)0.0004 (9)
O1B0.0127 (8)0.0147 (9)0.0184 (8)0.0006 (7)0.0038 (7)0.0024 (7)
O2B0.0140 (8)0.0130 (8)0.0209 (9)0.0027 (7)0.0048 (7)0.0015 (7)
O3B0.0194 (9)0.0105 (9)0.0185 (9)0.0008 (7)0.0009 (7)0.0015 (7)
O4B0.0169 (9)0.0173 (9)0.0147 (8)0.0047 (7)0.0084 (7)0.0016 (7)
O5B0.0158 (8)0.0154 (9)0.0154 (8)0.0003 (7)0.0067 (7)0.0022 (7)
O6B0.0235 (10)0.0111 (9)0.0204 (9)0.0018 (8)0.0020 (8)0.0001 (7)
C1B0.0154 (12)0.0191 (13)0.0187 (11)0.0040 (10)0.0045 (9)0.0032 (10)
C2B0.0127 (11)0.0115 (11)0.0146 (10)0.0004 (9)0.0041 (8)0.0028 (9)
C3B0.0124 (10)0.0095 (10)0.0120 (10)0.0013 (9)0.0022 (8)0.0000 (8)
C4B0.0119 (10)0.0115 (11)0.0136 (10)0.0022 (9)0.0050 (8)0.0004 (8)
C5B0.0135 (10)0.0101 (10)0.0146 (10)0.0027 (9)0.0070 (8)0.0012 (8)
C6B0.0117 (10)0.0132 (12)0.0217 (12)0.0002 (9)0.0034 (9)0.0010 (10)
C7B0.0175 (12)0.0170 (13)0.0228 (12)0.0009 (10)0.0101 (10)0.0057 (10)
Geometric parameters (Å, º) top
O1A—C1A1.425 (3)O1B—C1B1.426 (3)
O1A—H1OA0.84O1B—H1OB0.84
O2A—C7A1.412 (3)O2B—C7B1.409 (3)
O2A—C2A1.440 (3)O2B—C2B1.432 (3)
O3A—C3A1.424 (3)O3B—C3B1.432 (3)
O3A—H3OA0.84O3B—H3OB0.84
O4A—C4A1.433 (3)O4B—C4B1.430 (3)
O4A—H4OA0.84O4B—H4OB0.84
O5A—C7A1.404 (3)O5B—C7B1.407 (3)
O5A—C5A1.436 (3)O5B—C5B1.435 (3)
O6A—C6A1.427 (3)O6B—C6B1.428 (3)
O6A—H6OA0.84O6B—H6OB0.84
C1A—C2A1.513 (4)C1B—C2B1.525 (4)
C1A—H1A10.99C1B—H1B10.99
C1A—H1A20.99C1B—H1B20.99
C2A—C3A1.527 (3)C2B—C3B1.537 (4)
C2A—H2A1.00C2B—H2B1.00
C3A—C4A1.527 (3)C3B—C4B1.525 (4)
C3A—H3A1.00C3B—H3B1.00
C4A—C5A1.538 (3)C4B—C5B1.533 (3)
C4A—H4A1.00C4B—H4B1.00
C5A—C6A1.519 (4)C5B—C6B1.521 (4)
C5A—H5A1.00C5B—H5B1.00
C6A—H6A10.99C6B—H6B10.99
C6A—H6A20.99C6B—H6B20.99
C7A—H7A10.99C7B—H7B10.99
C7A—H7A20.99C7B—H7B20.99
C1A—O1A—H1OA109.5C1B—O1B—H1OB109.5
C7A—O2A—C2A113.60 (18)C7B—O2B—C2B114.7 (2)
C3A—O3A—H3OA109.5C3B—O3B—H3OB109.5
C4A—O4A—H4OA109.5C4B—O4B—H4OB109.5
C7A—O5A—C5A113.94 (19)C7B—O5B—C5B114.20 (19)
C6A—O6A—H6OA109.5C6B—O6B—H6OB109.5
O1A—C1A—C2A111.2 (2)O1B—C1B—C2B110.9 (2)
O1A—C1A—H1A1109.4O1B—C1B—H1B1109.5
C2A—C1A—H1A1109.4C2B—C1B—H1B1109.5
O1A—C1A—H1A2109.4O1B—C1B—H1B2109.5
C2A—C1A—H1A2109.4C2B—C1B—H1B2109.5
H1A1—C1A—H1A2108.0H1B1—C1B—H1B2108.0
O2A—C2A—C1A106.35 (19)O2B—C2B—C1B107.2 (2)
O2A—C2A—C3A107.41 (19)O2B—C2B—C3B108.86 (19)
C1A—C2A—C3A112.4 (2)C1B—C2B—C3B111.5 (2)
O2A—C2A—H2A110.2O2B—C2B—H2B109.8
C1A—C2A—H2A110.2C1B—C2B—H2B109.8
C3A—C2A—H2A110.2C3B—C2B—H2B109.8
O3A—C3A—C2A107.86 (19)O3B—C3B—C4B107.1 (2)
O3A—C3A—C4A110.03 (19)O3B—C3B—C2B108.9 (2)
C2A—C3A—C4A114.24 (19)C4B—C3B—C2B117.1 (2)
O3A—C3A—H3A108.2O3B—C3B—H3B107.8
C2A—C3A—H3A108.2C4B—C3B—H3B107.8
C4A—C3A—H3A108.2C2B—C3B—H3B107.8
O4A—C4A—C3A106.92 (18)O4B—C4B—C3B108.3 (2)
O4A—C4A—C5A109.79 (19)O4B—C4B—C5B110.0 (2)
C3A—C4A—C5A114.77 (19)C3B—C4B—C5B116.0 (2)
O4A—C4A—H4A108.4O4B—C4B—H4B107.4
C3A—C4A—H4A108.4C3B—C4B—H4B107.4
C5A—C4A—H4A108.4C5B—C4B—H4B107.4
O5A—C5A—C6A107.1 (2)O5B—C5B—C6B107.1 (2)
O5A—C5A—C4A106.90 (19)O5B—C5B—C4B108.63 (19)
C6A—C5A—C4A110.9 (2)C6B—C5B—C4B111.7 (2)
O5A—C5A—H5A110.6O5B—C5B—H5B109.8
C6A—C5A—H5A110.6C6B—C5B—H5B109.8
C4A—C5A—H5A110.6C4B—C5B—H5B109.8
O6A—C6A—C5A109.5 (2)O6B—C6B—C5B111.3 (2)
O6A—C6A—H6A1109.8O6B—C6B—H6B1109.4
C5A—C6A—H6A1109.8C5B—C6B—H6B1109.4
O6A—C6A—H6A2109.8O6B—C6B—H6B2109.4
C5A—C6A—H6A2109.8C5B—C6B—H6B2109.4
H6A1—C6A—H6A2108.2H6B1—C6B—H6B2108.0
O5A—C7A—O2A112.5 (2)O5B—C7B—O2B113.0 (2)
O5A—C7A—H7A1109.1O5B—C7B—H7B1109.0
O2A—C7A—H7A1109.1O2B—C7B—H7B1109.0
O5A—C7A—H7A2109.1O5B—C7B—H7B2109.0
O2A—C7A—H7A2109.1O2B—C7B—H7B2109.0
H7A1—C7A—H7A2107.8H7B1—C7B—H7B2107.8
C7A—O2A—C2A—C1A142.6 (2)C7B—O2B—C2B—C1B145.2 (2)
C7A—O2A—C2A—C3A96.8 (2)C7B—O2B—C2B—C3B94.1 (2)
O1A—C1A—C2A—O2A63.7 (3)O1B—C1B—C2B—O2B60.0 (3)
O1A—C1A—C2A—C3A179.0 (2)O1B—C1B—C2B—C3B59.0 (3)
O2A—C2A—C3A—O3A167.88 (18)O2B—C2B—C3B—O3B175.93 (19)
C1A—C2A—C3A—O3A51.2 (3)C1B—C2B—C3B—O3B57.9 (3)
O2A—C2A—C3A—C4A69.5 (2)O2B—C2B—C3B—C4B62.5 (3)
C1A—C2A—C3A—C4A173.9 (2)C1B—C2B—C3B—C4B179.5 (2)
O3A—C3A—C4A—O4A68.6 (2)O3B—C3B—C4B—O4B73.1 (2)
C2A—C3A—C4A—O4A169.94 (18)C2B—C3B—C4B—O4B164.4 (2)
O3A—C3A—C4A—C5A169.39 (19)O3B—C3B—C4B—C5B162.8 (2)
C2A—C3A—C4A—C5A47.9 (3)C2B—C3B—C4B—C5B40.3 (3)
C7A—O5A—C5A—C6A143.6 (2)C7B—O5B—C5B—C6B143.3 (2)
C7A—O5A—C5A—C4A97.5 (2)C7B—O5B—C5B—C4B95.9 (2)
O4A—C4A—C5A—O5A172.23 (19)O4B—C4B—C5B—O5B173.92 (19)
C3A—C4A—C5A—O5A67.3 (3)C3B—C4B—C5B—O5B62.8 (3)
O4A—C4A—C5A—C6A55.9 (3)O4B—C4B—C5B—C6B56.0 (3)
C3A—C4A—C5A—C6A176.3 (2)C3B—C4B—C5B—C6B179.3 (2)
O5A—C5A—C6A—O6A58.5 (3)O5B—C5B—C6B—O6B72.3 (3)
C4A—C5A—C6A—O6A174.8 (2)C4B—C5B—C6B—O6B168.9 (2)
C5A—O5A—C7A—O2A49.5 (3)C5B—O5B—C7B—O2B48.5 (3)
C2A—O2A—C7A—O5A45.2 (3)C2B—O2B—C7B—O5B46.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O6Bi0.841.952.765 (3)164
O3A—H3OA···O6Aii0.841.842.679 (3)173
O4A—H4OA···O1Aiii0.841.852.678 (3)167
O6A—H6OA···O1Biv0.841.872.705 (3)175
O1B—H1OB···O4Bii0.841.972.726 (3)150
O3B—H3OB···O4A0.841.882.716 (3)172
O4B—H4OB···O3Aiii0.842.022.854 (3)173
O6B—H6OB···O3Bv0.841.992.781 (3)156
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z; (iii) x+1, y1/2, z+1; (iv) x+1, y, z; (v) x+2, y1/2, z+2.
(III) 4(R),7(R)-di-(hydroxymethyl)-5(R),6(R)-dihydroxy-1,3-dioxepane sodium iodide top
Crystal data top
NaI·C7H14O6F(000) = 672
Mr = 344.07Dx = 1.876 Mg m3
Orthorhombic, C2221Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2Cell parameters from 25 reflections
a = 6.948 (3) Åθ = 22.0–31.3°
b = 11.4543 (6) ŵ = 2.67 mm1
c = 15.3050 (7) ÅT = 297 K
V = 1218.1 (5) Å3Prism, colorless
Z = 40.38 × 0.32 × 0.20 mm
Data collection top
Enraf Nonius CAD4
diffractometer
Rint = 0.019
ω–2θ scansθmax = 40.0°, θmin = 2.7°
Absorption correction: ψ scan
(North et al., 1968)
h = 012
Tmin = 0.430, Tmax = 0.598k = 020
3069 measured reflectionsl = 2127
2871 independent reflections3 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)] = 0.021Δρmax = 0.66 e Å3
wR(F2) = 0.059Δρmin = 0.86 e Å3
S = 1.09Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2871 reflectionsExtinction coefficient: 0.0144 (5)
73 parametersAbsolute structure: Flack (1983), 758 Friedel pairs
0 restraintsAbsolute 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
xyzUiso*/Ueq
O10.5555 (2)0.14990 (15)0.64110 (13)0.0599 (4)
H1O0.48040.11240.61070.09*
O20.84362 (16)0.26345 (9)0.72186 (10)0.0380 (2)
O30.91871 (19)0.04362 (10)0.66643 (9)0.0403 (2)
H3O0.99950.03560.62790.06*
C10.7346 (3)0.16201 (17)0.59629 (13)0.0491 (4)
H1A0.73320.23190.56050.059*
H1B0.75590.09520.55850.059*
C20.8930 (2)0.16997 (13)0.66356 (11)0.0359 (3)
H21.01560.18720.63470.043*
C30.9130 (2)0.05947 (11)0.71928 (10)0.0325 (2)
H30.79760.05420.75590.039*
C710.33228 (18)0.750.0431 (5)
H70.95840.38210.79760.052*
I0.74135 (2)010.04623 (6)
Na10.21442 (9)0.750.0396 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0386 (6)0.0671 (9)0.0741 (10)0.0018 (6)0.0123 (7)0.0269 (8)
O20.0276 (4)0.0286 (4)0.0578 (7)0.0022 (3)0.0010 (5)0.0051 (4)
O30.0467 (6)0.0284 (4)0.0456 (6)0.0005 (4)0.0055 (5)0.0062 (4)
C10.0527 (10)0.0441 (8)0.0503 (8)0.0073 (8)0.0089 (8)0.0016 (6)
C20.0340 (6)0.0286 (5)0.0452 (8)0.0039 (5)0.0023 (5)0.0005 (5)
C30.0304 (6)0.0254 (5)0.0418 (7)0.0004 (4)0.0051 (5)0.0027 (5)
C70.0306 (8)0.0243 (7)0.0746 (16)00.0058 (10)0
I0.04411 (8)0.05565 (10)0.03894 (8)000.00966 (6)
Na0.0312 (4)0.0280 (4)0.0595 (6)00.0008 (4)0
Geometric parameters (Å, º) top
O1—C11.428 (3)C2—H20.98
O1—H1O0.82C3—C3ii1.532 (3)
O2—C71.4098 (15)C3—H30.98
O2—C21.4354 (19)C7—O2ii1.4098 (15)
O2—Nai2.4393 (11)C7—H70.97
O3—C31.4318 (17)Na—O1iii2.3112 (17)
O3—H3O0.82Na—O1iv2.3112 (17)
C1—C21.510 (2)Na—O2iii2.4393 (11)
C1—H1A0.97Na—O2iv2.4393 (11)
C1—H1B0.97Na—O3ii2.4047 (15)
C2—C31.533 (2)
C1—O1—H1O109.5C3ii—C3—C2114.41 (10)
C7—O2—C2115.02 (11)O3—C3—H3107.1
C7—O2—Nai129.96 (9)C3ii—C3—H3107.1
C2—O2—Nai114.91 (9)C2—C3—H3107.1
C3—O3—H3O109.5O2—C7—O2ii112.00 (16)
O1—C1—C2108.28 (16)O2—C7—H7109.2
O1—C1—H1A110.0O2ii—C7—H7109.2
C2—C1—H1A110.0H7—C7—H7ii107.9
O1—C1—H1B110.0O1iii—Na—O1iv95.49 (11)
C2—C1—H1B110.0O1iii—Na—O3ii153.05 (5)
H1A—C1—H1B108.4O1iv—Na—O3ii101.69 (6)
O2—C2—C1107.15 (13)O1iii—Na—O2iii68.87 (5)
O2—C2—C3106.97 (13)O1iv—Na—O2iii102.75 (5)
C1—C2—C3113.31 (13)O3ii—Na—O2iii87.05 (4)
O2—C2—H2109.8O1iii—Na—O2iv102.75 (5)
C1—C2—H2109.8O1iv—Na—O2iv68.87 (5)
C3—C2—H2109.8O3ii—Na—O2iv102.74 (5)
O3—C3—C3ii108.97 (10)O2iii—Na—O2iv168.07 (7)
O3—C3—C2111.67 (12)
C7—O2—C2—C1141.66 (14)C1—C2—C3—O348.90 (17)
Nai—O2—C2—C134.89 (16)O2—C2—C3—C3ii68.89 (17)
C7—O2—C2—C396.52 (15)C2—C3—C3ii—C2ii49.82 (17)
Nai—O2—C2—C386.93 (12)O3—C3—C3ii—O3ii58.61 (15)
O1—C1—C2—O254.50 (18)C1—C2—C3—C3ii173.26 (15)
O1—C1—C2—C363.25 (18)C2—O2—C7—O2ii47.30 (10)
O2—C2—C3—O3166.75 (12)Nai—O2—C7—O2ii136.78 (14)
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+2, y, z+3/2; (iii) x+1/2, y1/2, z; (iv) x+3/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···Iv0.822.633.4447 (14)174
O3—H3O···Ivi0.822.693.5095 (13)177
Symmetry codes: (v) x+1, y, z1/2; (vi) x+2, y, z1/2.
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) top
Atoms1Aa1Ba2Aa2BaNaIcmplxabcd
C2/C3/C4/C543.8 (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/C396.57 (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/C496.99 (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/O260.42 (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/O665.76 (9)56.26 (19)58.5 (3)72.3 (3)-54.50 (18)-53.8 (2)-172.0 (4)68.8 (4)
 

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