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The structure of the title compound, C18H14O8, adopts a symmetric trans-configuration of the bisindane rings across the C2-C2' bond, with this bond lying across an inversion centre. The hydrogen-bonding network consists of associations from the hydroxyl groups to adjacent water O atoms and then from the water H atoms to the keto O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012145/ac6042sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012145/ac6042Isup2.hkl
Contains datablock I

CCDC reference: 221684

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.116
  • Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

2,2'-Dihydroxy-[2,2'-bi-1H-indene]-1,1',3,3'-(2H,2'H)-tetrone dihydrate top
Crystal data top
C18H10O6·2H2ODx = 1.449 Mg m3
Mr = 358.29Melting point: dec 522-527 K K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.4479 (4) ÅCell parameters from 4659 reflections
b = 12.4759 (6) Åθ = 2.9–27.5°
c = 7.9293 (4) ŵ = 0.12 mm1
β = 100.634 (3)°T = 120 K
V = 821.36 (7) Å3Prism, colourless
Z = 20.14 × 0.08 × 0.03 mm
F(000) = 372
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
1884 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode1197 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.090
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
φ and ω scansh = 1010
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
k = 1616
Tmin = 0.984, Tmax = 0.997l = 1010
10673 measured reflections
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)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0513P)2 + 0.0592P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1884 reflectionsΔρmax = 0.26 e Å3
131 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7117 (2)0.06010 (16)0.0924 (2)0.0239 (5)
O10.75941 (16)0.13773 (11)0.02403 (17)0.0299 (4)
C20.5333 (2)0.03055 (15)0.0843 (2)0.0211 (5)
O20.43129 (16)0.11816 (11)0.09039 (18)0.0269 (4)
H20.472 (3)0.155 (2)0.196 (3)0.062 (8)*
C30.5463 (2)0.04654 (16)0.2394 (2)0.0228 (5)
O30.43417 (16)0.06824 (12)0.31009 (17)0.0321 (4)
C40.7810 (3)0.15905 (17)0.4053 (3)0.0309 (5)
H40.71560.20040.46600.039*
C50.9461 (3)0.17471 (19)0.4294 (3)0.0389 (6)
H50.99440.22900.50600.049*
C61.0418 (3)0.1126 (2)0.3439 (3)0.0388 (6)
H61.15470.12510.36340.048*
C70.9774 (2)0.03299 (18)0.2310 (3)0.0328 (5)
H71.04410.01020.17440.041*
C90.7149 (2)0.08074 (16)0.2891 (2)0.0237 (5)
C80.8116 (2)0.01823 (16)0.2032 (2)0.0242 (5)
O1W0.4171 (2)0.31775 (14)0.1101 (2)0.0348 (4)
H1W0.377 (4)0.254 (3)0.084 (4)0.092 (12)*
H2W0.429 (3)0.351 (3)0.016 (5)0.073 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0238 (10)0.0246 (11)0.0228 (10)0.0027 (8)0.0033 (8)0.0024 (9)
O10.0281 (8)0.0272 (8)0.0337 (8)0.0053 (6)0.0036 (6)0.0057 (7)
C20.0199 (10)0.0192 (10)0.0235 (10)0.0022 (7)0.0022 (8)0.0005 (8)
O20.0261 (8)0.0254 (8)0.0274 (8)0.0074 (6)0.0005 (6)0.0035 (6)
C30.0232 (11)0.0236 (11)0.0211 (9)0.0018 (8)0.0027 (8)0.0024 (8)
O30.0250 (8)0.0415 (9)0.0304 (8)0.0019 (6)0.0063 (6)0.0056 (7)
C40.0306 (12)0.0284 (12)0.0324 (11)0.0010 (9)0.0021 (9)0.0054 (9)
C50.0333 (13)0.0391 (14)0.0409 (13)0.0091 (10)0.0021 (11)0.0089 (11)
C60.0216 (11)0.0509 (15)0.0421 (13)0.0083 (10)0.0013 (10)0.0065 (11)
C70.0237 (11)0.0427 (14)0.0318 (11)0.0009 (9)0.0046 (9)0.0034 (10)
C90.0234 (10)0.0234 (11)0.0232 (10)0.0008 (8)0.0018 (8)0.0012 (8)
C80.0210 (10)0.0268 (11)0.0233 (10)0.0005 (8)0.0003 (8)0.0001 (8)
O1W0.0447 (10)0.0305 (10)0.0273 (9)0.0057 (7)0.0018 (7)0.0001 (7)
Geometric parameters (Å, º) top
C1—O11.214 (2)C4—H40.95
C1—C81.471 (3)C5—C61.384 (3)
C1—C21.542 (3)C5—H50.95
C2—O21.398 (2)C6—C71.380 (3)
C2—C31.549 (3)C6—H60.95
C2—C2i1.552 (4)C7—C81.390 (3)
O2—H20.96 (3)C7—H70.95
C3—O31.217 (2)C9—C81.395 (3)
C3—C91.469 (3)O1W—H1W0.88 (4)
C4—C51.386 (3)O1W—H2W0.88 (4)
C4—C91.388 (3)
O1—C1—C8126.53 (18)C6—C5—C4121.2 (2)
O1—C1—C2125.07 (17)C6—C5—H5119.4
C8—C1—C2108.34 (16)C4—C5—H5119.4
O2—C2—C1114.56 (16)C5—C6—C7121.6 (2)
O2—C2—C3114.34 (15)C5—C6—H6119.2
C1—C2—C3100.94 (14)C7—C6—H6119.2
O2—C2—C2i106.63 (18)C6—C7—C8117.6 (2)
C1—C2—C2i110.44 (19)C6—C7—H7121.2
C3—C2—C2i109.90 (18)C8—C7—H7121.2
C2—O2—H2106.0 (16)C4—C9—C8121.16 (18)
O3—C3—C9127.62 (18)C4—C9—C3129.35 (18)
O3—C3—C2123.82 (17)C8—C9—C3109.46 (17)
C9—C3—C2108.45 (16)C7—C8—C9120.84 (18)
C5—C4—C9117.5 (2)C7—C8—C1129.28 (19)
C5—C4—H4121.2C9—C8—C1109.86 (17)
C9—C4—H4121.2H1W—O1W—H2W110 (3)
O1—C1—C2—O237.6 (3)C5—C4—C9—C3179.4 (2)
C8—C1—C2—O2139.56 (16)O3—C3—C9—C412.8 (3)
O1—C1—C2—C3160.97 (19)C2—C3—C9—C4171.02 (19)
C8—C1—C2—C316.20 (19)O3—C3—C9—C8165.2 (2)
O1—C1—C2—C2i82.8 (3)C2—C3—C9—C811.0 (2)
C8—C1—C2—C2i100.0 (2)C6—C7—C8—C91.1 (3)
O2—C2—C3—O336.5 (2)C6—C7—C8—C1179.4 (2)
C1—C2—C3—O3160.04 (19)C4—C9—C8—C70.3 (3)
C2i—C2—C3—O383.3 (3)C3—C9—C8—C7178.50 (18)
O2—C2—C3—C9139.84 (17)C4—C9—C8—C1178.31 (18)
C1—C2—C3—C916.32 (19)C3—C9—C8—C10.1 (2)
C2i—C2—C3—C9100.3 (2)O1—C1—C8—C712.2 (3)
C9—C4—C5—C61.6 (3)C2—C1—C8—C7170.7 (2)
C4—C5—C6—C70.2 (4)O1—C1—C8—C9166.29 (19)
C5—C6—C7—C81.2 (3)C2—C1—C8—C910.8 (2)
C5—C4—C9—C81.7 (3)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1Wii0.96 (3)1.68 (3)2.607 (2)161 (3)
O1W—H1W···O1i0.88 (4)1.95 (4)2.795 (2)162 (3)
O1W—H2W···O3iii0.88 (4)1.93 (4)2.798 (2)174 (3)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1/2, z+1/2; (iii) x, y+1/2, z1/2.
 

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