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The title compound, C10H6O8·2H2O, has been previously studied by single-crystal X-ray diffraction at room temperature [Takusagawa et al. (1971) Bull. Chem. Soc. Jpn, 44, 1274-1278]. We present here a redetermination of the structure at 160 K, resulting in a considerably improved precision. The organic molecule has crystallographic inversion symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014351/bt6288sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014351/bt6288Isup2.hkl
Contains datablock I

CCDC reference: 221667

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.096
  • Data-to-parameter ratio = 10.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

(I) top
Crystal data top
C10H6O8·2H2OZ = 1
Mr = 290.18F(000) = 150
Triclinic, P1Dx = 1.666 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.4651 (6) ÅCell parameters from 1682 reflections
b = 6.4044 (7) Åθ = 3.5–28.4°
c = 9.1145 (11) ŵ = 0.15 mm1
α = 71.941 (3)°T = 160 K
β = 88.612 (3)°Plate, colourless
γ = 72.933 (3)°0.48 × 0.42 × 0.09 mm
V = 289.16 (6) Å3
Data collection top
Bruker SMART 1K CCD
diffractometer
890 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
ω rotation with narrow frames scansh = 66
1735 measured reflectionsk = 76
1010 independent reflectionsl = 109
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: All non-H atoms found by direct methods
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: Geom except H1W&H2W coords freely refined
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0698P)2 + 0.025P]
where P = (Fo2 + 2Fc2)/3
1010 reflections(Δ/σ)max < 0.001
99 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
C10.5163 (3)0.5658 (3)0.33991 (17)0.0186 (3)
C20.3875 (2)0.4051 (2)0.41155 (16)0.0186 (4)
C30.3710 (3)0.3411 (2)0.57104 (16)0.0190 (4)
H30.28240.23330.61930.023*
C40.5177 (3)0.6566 (2)0.16703 (16)0.0190 (3)
O10.3269 (2)0.7850 (2)0.08578 (12)0.0286 (3)
O20.7443 (2)0.5934 (2)0.11496 (12)0.0263 (3)
H20.73150.64320.01780.040*
C50.2794 (3)0.2929 (2)0.31782 (16)0.0186 (3)
O30.3523 (2)0.29257 (19)0.19038 (12)0.0260 (3)
O40.1121 (2)0.19434 (19)0.38730 (12)0.0256 (3)
H40.05480.13900.32820.038*
O1W0.0787 (2)1.0165 (2)0.21940 (13)0.0229 (3)
H1W0.035 (4)0.942 (4)0.173 (2)0.034*
H2W0.184 (4)1.101 (4)0.148 (2)0.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0189 (7)0.0209 (7)0.0152 (7)0.0042 (6)0.0023 (5)0.0065 (6)
C20.0176 (7)0.0223 (8)0.0157 (8)0.0045 (6)0.0019 (6)0.0074 (6)
C30.0200 (7)0.0206 (7)0.0160 (8)0.0064 (6)0.0027 (6)0.0051 (6)
C40.0231 (7)0.0205 (7)0.0165 (8)0.0085 (6)0.0018 (6)0.0084 (6)
O10.0272 (6)0.0363 (6)0.0159 (6)0.0017 (5)0.0014 (4)0.0070 (5)
O20.0242 (6)0.0401 (7)0.0128 (6)0.0080 (5)0.0045 (4)0.0075 (5)
C50.0185 (7)0.0208 (7)0.0153 (7)0.0036 (6)0.0006 (6)0.0064 (6)
O30.0297 (6)0.0380 (7)0.0173 (6)0.0143 (5)0.0054 (5)0.0147 (5)
O40.0319 (6)0.0352 (7)0.0193 (6)0.0195 (5)0.0054 (5)0.0134 (5)
O1W0.0252 (6)0.0263 (6)0.0182 (6)0.0081 (5)0.0002 (5)0.0079 (5)
Geometric parameters (Å, º) top
C1—C3i1.391 (2)C4—O21.3113 (18)
C1—C21.402 (2)O2—H20.8400
C1—C41.502 (2)C5—O31.2191 (18)
C2—C31.391 (2)C5—O41.3033 (19)
C2—C51.500 (2)O4—H40.8400
C3—H30.9500O1W—H1W0.85 (2)
C4—O11.2120 (18)O1W—H2W0.81 (2)
C3i—C1—C2119.78 (14)O1—C4—O2124.00 (13)
C3i—C1—C4118.28 (13)O1—C4—C1122.03 (13)
C2—C1—C4121.73 (13)O2—C4—C1113.89 (12)
C3—C2—C1119.94 (13)C4—O2—H2109.5
C3—C2—C5119.82 (13)O3—C5—O4125.09 (13)
C1—C2—C5120.16 (13)O3—C5—C2121.02 (13)
C1i—C3—C2120.27 (14)O4—C5—C2113.87 (12)
C1i—C3—H3119.9C5—O4—H4109.5
C2—C3—H3119.9H1W—O1W—H2W101.7 (19)
C3i—C1—C2—C30.6 (2)C2—C1—C4—O169.8 (2)
C4—C1—C2—C3174.16 (12)C3i—C1—C4—O271.86 (17)
C3i—C1—C2—C5176.23 (12)C2—C1—C4—O2113.34 (15)
C4—C1—C2—C59.0 (2)C3—C2—C5—O3158.54 (13)
C1—C2—C3—C1i0.6 (2)C1—C2—C5—O318.3 (2)
C5—C2—C3—C1i176.24 (12)C3—C2—C5—O419.59 (18)
C3i—C1—C4—O1104.97 (17)C1—C2—C5—O4163.60 (13)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O10.85 (2)1.92 (2)2.7664 (16)171.6 (18)
O2—H2···O3ii0.841.852.6724 (14)165
O4—H4···O1Wiii0.841.732.5656 (14)175
O1W—H2W···O1iv0.81 (2)2.11 (2)2.8586 (16)152.0 (19)
O1W—H2W···O3v0.81 (2)2.55 (2)3.0642 (16)122.4 (17)
Symmetry codes: (ii) x+1, y+1, z; (iii) x, y1, z; (iv) x, y+2, z; (v) x1, y+1, z.
 

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