2,2'-Di­hydroxy-[2,2'-bi-1H-indene]-1,1',3,3'-(2H,2'H)-tetrone dihydrate

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.

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

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Computing details

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

Crystal data

C18H10O6·2H2O	Dx = 1.449 Mg m^−3
Mr = 358.29	Melting point: dec 522-527 K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4479 (4) Å	Cell parameters from 4659 reflections
b = 12.4759 (6) Å	θ = 2.9–27.5°
c = 7.9293 (4) Å	µ = 0.12 mm^−1
β = 100.634 (3)°	T = 120 K
V = 821.36 (7) Å^3	Prism, colourless
Z = 2	0.14 × 0.08 × 0.03 mm
F(000) = 372

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	1884 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1197 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan SORTAV (Blessing, 1995)	k = −16→16
Tmin = 0.984, Tmax = 0.997	l = −10→10
10673 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 0.0592P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
1884 reflections	Δρmax = 0.26 e Å^−3
131 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (5)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7117 (2)	−0.06010 (16)	0.0924 (2)	0.0239 (5)
O1	0.75941 (16)	−0.13773 (11)	0.02403 (17)	0.0299 (4)
C2	0.5333 (2)	−0.03055 (15)	0.0843 (2)	0.0211 (5)
O2	0.43129 (16)	−0.11816 (11)	0.09039 (18)	0.0269 (4)
H2	0.472 (3)	−0.155 (2)	0.196 (3)	0.062 (8)*
C3	0.5463 (2)	0.04654 (16)	0.2394 (2)	0.0228 (5)
O3	0.43417 (16)	0.06824 (12)	0.31009 (17)	0.0321 (4)
C4	0.7810 (3)	0.15905 (17)	0.4053 (3)	0.0309 (5)
H4	0.7156	0.2004	0.4660	0.039*
C5	0.9461 (3)	0.17471 (19)	0.4294 (3)	0.0389 (6)
H5	0.9944	0.2290	0.5060	0.049*
C6	1.0418 (3)	0.1126 (2)	0.3439 (3)	0.0388 (6)
H6	1.1547	0.1251	0.3634	0.048*
C7	0.9774 (2)	0.03299 (18)	0.2310 (3)	0.0328 (5)
H7	1.0441	−0.0102	0.1744	0.041*
C9	0.7149 (2)	0.08074 (16)	0.2891 (2)	0.0237 (5)
C8	0.8116 (2)	0.01823 (16)	0.2032 (2)	0.0242 (5)
O1W	0.4171 (2)	0.31775 (14)	0.1101 (2)	0.0348 (4)
H1W	0.377 (4)	0.254 (3)	0.084 (4)	0.092 (12)*
H2W	0.429 (3)	0.351 (3)	0.016 (5)	0.073 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0238 (10)	0.0246 (11)	0.0228 (10)	0.0027 (8)	0.0033 (8)	0.0024 (9)
O1	0.0281 (8)	0.0272 (8)	0.0337 (8)	0.0053 (6)	0.0036 (6)	−0.0057 (7)
C2	0.0199 (10)	0.0192 (10)	0.0235 (10)	−0.0022 (7)	0.0022 (8)	0.0005 (8)
O2	0.0261 (8)	0.0254 (8)	0.0274 (8)	−0.0074 (6)	0.0005 (6)	0.0035 (6)
C3	0.0232 (11)	0.0236 (11)	0.0211 (9)	0.0018 (8)	0.0027 (8)	0.0024 (8)
O3	0.0250 (8)	0.0415 (9)	0.0304 (8)	0.0019 (6)	0.0063 (6)	−0.0056 (7)
C4	0.0306 (12)	0.0284 (12)	0.0324 (11)	−0.0010 (9)	0.0021 (9)	−0.0054 (9)
C5	0.0333 (13)	0.0391 (14)	0.0409 (13)	−0.0091 (10)	−0.0021 (11)	−0.0089 (11)
C6	0.0216 (11)	0.0509 (15)	0.0421 (13)	−0.0083 (10)	0.0013 (10)	−0.0065 (11)
C7	0.0237 (11)	0.0427 (14)	0.0318 (11)	0.0009 (9)	0.0046 (9)	−0.0034 (10)
C9	0.0234 (10)	0.0234 (11)	0.0232 (10)	0.0008 (8)	0.0018 (8)	0.0012 (8)
C8	0.0210 (10)	0.0268 (11)	0.0233 (10)	−0.0005 (8)	−0.0003 (8)	−0.0001 (8)
O1W	0.0447 (10)	0.0305 (10)	0.0273 (9)	−0.0057 (7)	0.0018 (7)	−0.0001 (7)

Geometric parameters (Å, º)

C1—O1	1.214 (2)	C4—H4	0.95
C1—C8	1.471 (3)	C5—C6	1.384 (3)
C1—C2	1.542 (3)	C5—H5	0.95
C2—O2	1.398 (2)	C6—C7	1.380 (3)
C2—C3	1.549 (3)	C6—H6	0.95
C2—C2^i	1.552 (4)	C7—C8	1.390 (3)
O2—H2	0.96 (3)	C7—H7	0.95
C3—O3	1.217 (2)	C9—C8	1.395 (3)
C3—C9	1.469 (3)	O1W—H1W	0.88 (4)
C4—C5	1.386 (3)	O1W—H2W	0.88 (4)
C4—C9	1.388 (3)
O1—C1—C8	126.53 (18)	C6—C5—C4	121.2 (2)
O1—C1—C2	125.07 (17)	C6—C5—H5	119.4
C8—C1—C2	108.34 (16)	C4—C5—H5	119.4
O2—C2—C1	114.56 (16)	C5—C6—C7	121.6 (2)
O2—C2—C3	114.34 (15)	C5—C6—H6	119.2
C1—C2—C3	100.94 (14)	C7—C6—H6	119.2
O2—C2—C2^i	106.63 (18)	C6—C7—C8	117.6 (2)
C1—C2—C2^i	110.44 (19)	C6—C7—H7	121.2
C3—C2—C2^i	109.90 (18)	C8—C7—H7	121.2
C2—O2—H2	106.0 (16)	C4—C9—C8	121.16 (18)
O3—C3—C9	127.62 (18)	C4—C9—C3	129.35 (18)
O3—C3—C2	123.82 (17)	C8—C9—C3	109.46 (17)
C9—C3—C2	108.45 (16)	C7—C8—C9	120.84 (18)
C5—C4—C9	117.5 (2)	C7—C8—C1	129.28 (19)
C5—C4—H4	121.2	C9—C8—C1	109.86 (17)
C9—C4—H4	121.2	H1W—O1W—H2W	110 (3)
O1—C1—C2—O2	37.6 (3)	C5—C4—C9—C3	179.4 (2)
C8—C1—C2—O2	−139.56 (16)	O3—C3—C9—C4	−12.8 (3)
O1—C1—C2—C3	160.97 (19)	C2—C3—C9—C4	171.02 (19)
C8—C1—C2—C3	−16.20 (19)	O3—C3—C9—C8	165.2 (2)
O1—C1—C2—C2^i	−82.8 (3)	C2—C3—C9—C8	−11.0 (2)
C8—C1—C2—C2^i	100.0 (2)	C6—C7—C8—C9	−1.1 (3)
O2—C2—C3—O3	−36.5 (2)	C6—C7—C8—C1	−179.4 (2)
C1—C2—C3—O3	−160.04 (19)	C4—C9—C8—C7	−0.3 (3)
C2^i—C2—C3—O3	83.3 (3)	C3—C9—C8—C7	−178.50 (18)
O2—C2—C3—C9	139.84 (17)	C4—C9—C8—C1	178.31 (18)
C1—C2—C3—C9	16.32 (19)	C3—C9—C8—C1	0.1 (2)
C2^i—C2—C3—C9	−100.3 (2)	O1—C1—C8—C7	12.2 (3)
C9—C4—C5—C6	−1.6 (3)	C2—C1—C8—C7	−170.7 (2)
C4—C5—C6—C7	0.2 (4)	O1—C1—C8—C9	−166.29 (19)
C5—C6—C7—C8	1.2 (3)	C2—C1—C8—C9	10.8 (2)
C5—C4—C9—C8	1.7 (3)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1W^ii	0.96 (3)	1.68 (3)	2.607 (2)	161 (3)
O1W—H1W···O1^i	0.88 (4)	1.95 (4)	2.795 (2)	162 (3)
O1W—H2W···O3^iii	0.88 (4)	1.93 (4)	2.798 (2)	174 (3)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2.