rac-2-Hy-droxy-2-(2-oxocyclo-pent-yl)-1H-indene-1,3(2H)-dione.

In the title compound, C(14)H(12)O(4), the indene unit is essentially planar [r.m.s. deviation = 0.0309 (1) Å] and the cyclo-penta-none ring adopts a twist form. In the crystal, mol-ecules are joined via pairs of O-H⋯O hydrogen bonds into centrosymmetric dimers.

Related literature

For a similar structure, see: Penthala et al. (2009 ▶).

Experimental

Crystal data

C14H12O4

M = 244.24

Triclinic,

a = 8.044 (3) Å

b = 8.404 (4) Å

c = 10.239 (3) Å

α = 66.95 (3)°

β = 74.36 (2)°

γ = 68.50 (3)°

V = 586.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.26 × 0.22 × 0.19 mm

Data collection

Nonius MACH3 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.974, T max = 0.981

2534 measured reflections

2054 independent reflections

1886 reflections with I > 2σ(I)

R int = 0.016

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.07

2054 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042856/gk2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042856/gk2301Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H12O4	Z = 2
Mr = 244.24	F(000) = 256
Triclinic, P1	Dx = 1.384 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.044 (3) Å	Cell parameters from 25 reflections
b = 8.404 (4) Å	θ = 2–25°
c = 10.239 (3) Å	µ = 0.10 mm−1
α = 66.95 (3)°	T = 293 K
β = 74.36 (2)°	Block, colourless
γ = 68.50 (3)°	0.26 × 0.22 × 0.19 mm
V = 586.1 (4) Å3

Nonius MACH3 diffractometer	1886 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
graphite	θmax = 25.0°, θmin = 2.2°
ω–2θ scans	h = −1→9
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.974, Tmax = 0.981	l = −11→12
2534 measured reflections	3 standard reflections every 60 min
2054 independent reflections	intensity decay: none

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2034P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2054 reflections	Δρmax = 0.25 e Å−3
164 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.059 (7)

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.

	x	y	z	Uiso*/Ueq
C1	0.4901 (2)	0.0143 (2)	0.33717 (14)	0.0367 (4)
C2	0.6584 (2)	−0.1372 (2)	0.32374 (19)	0.0505 (4)
H2A	0.7411	−0.1548	0.3852	0.061*
H2B	0.7191	−0.1129	0.2254	0.061*
C3	0.5929 (3)	−0.3013 (2)	0.3708 (2)	0.0551 (5)
H3A	0.5821	−0.3580	0.4742	0.066*
H3B	0.6745	−0.3896	0.3258	0.066*
C4	0.4084 (2)	−0.2245 (2)	0.3207 (2)	0.0494 (4)
H4A	0.3353	−0.3064	0.3719	0.059*
H4B	0.4206	−0.2008	0.2184	0.059*
C5	0.3268 (2)	−0.04868 (19)	0.35711 (15)	0.0367 (4)
H5	0.2797	−0.0818	0.4598	0.044*
C6	0.17097 (19)	0.09543 (19)	0.27852 (15)	0.0353 (3)
C7	0.2311 (2)	0.1817 (2)	0.11679 (15)	0.0387 (4)
C8	0.2136 (2)	0.3728 (2)	0.09029 (16)	0.0379 (4)
C9	0.2631 (2)	0.5004 (2)	−0.03520 (18)	0.0502 (4)
H9	0.3169	0.4710	−0.1186	0.060*
C10	0.2304 (3)	0.6721 (2)	−0.0329 (2)	0.0573 (5)
H10	0.2618	0.7600	−0.1163	0.069*
C11	0.1513 (3)	0.7168 (2)	0.0916 (2)	0.0561 (5)
H11	0.1308	0.8338	0.0902	0.067*
C12	0.1028 (2)	0.5900 (2)	0.21723 (19)	0.0470 (4)
H12	0.0508	0.6193	0.3008	0.056*
C13	0.13396 (19)	0.4179 (2)	0.21488 (16)	0.0366 (3)
C14	0.09696 (19)	0.2590 (2)	0.33215 (15)	0.0362 (3)
O1	0.48152 (16)	0.16243 (15)	0.33474 (12)	0.0484 (3)
O2	0.03172 (15)	0.02227 (15)	0.29221 (13)	0.0487 (3)
H2	−0.0080	−0.0170	0.3773	0.073*
O3	0.2801 (2)	0.10548 (17)	0.02872 (13)	0.0602 (4)
O4	0.01604 (16)	0.25544 (16)	0.45179 (12)	0.0502 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0390 (8)	0.0451 (9)	0.0268 (7)	−0.0147 (7)	−0.0051 (6)	−0.0103 (6)
C2	0.0385 (9)	0.0636 (11)	0.0529 (10)	−0.0090 (8)	−0.0067 (7)	−0.0282 (9)
C3	0.0563 (11)	0.0472 (10)	0.0590 (11)	0.0008 (8)	−0.0178 (8)	−0.0231 (8)
C4	0.0534 (10)	0.0382 (9)	0.0599 (10)	−0.0117 (7)	−0.0158 (8)	−0.0162 (7)
C5	0.0392 (8)	0.0369 (8)	0.0330 (7)	−0.0144 (6)	−0.0043 (6)	−0.0082 (6)
C6	0.0368 (8)	0.0355 (8)	0.0349 (7)	−0.0164 (6)	−0.0048 (6)	−0.0077 (6)
C7	0.0419 (8)	0.0409 (8)	0.0338 (8)	−0.0138 (6)	−0.0051 (6)	−0.0117 (6)
C8	0.0378 (8)	0.0392 (8)	0.0345 (7)	−0.0138 (6)	−0.0071 (6)	−0.0064 (6)
C9	0.0581 (10)	0.0529 (10)	0.0353 (8)	−0.0246 (8)	−0.0039 (7)	−0.0043 (7)
C10	0.0668 (12)	0.0465 (10)	0.0520 (10)	−0.0299 (9)	−0.0110 (9)	0.0044 (8)
C11	0.0639 (11)	0.0356 (9)	0.0691 (12)	−0.0193 (8)	−0.0185 (9)	−0.0073 (8)
C12	0.0483 (9)	0.0397 (9)	0.0527 (10)	−0.0113 (7)	−0.0083 (7)	−0.0158 (7)
C13	0.0335 (7)	0.0367 (8)	0.0372 (8)	−0.0108 (6)	−0.0057 (6)	−0.0087 (6)
C14	0.0312 (7)	0.0400 (8)	0.0343 (8)	−0.0118 (6)	−0.0028 (6)	−0.0091 (6)
O1	0.0516 (7)	0.0463 (7)	0.0537 (7)	−0.0207 (5)	−0.0116 (5)	−0.0145 (5)
O2	0.0464 (7)	0.0514 (7)	0.0525 (7)	−0.0268 (5)	−0.0123 (5)	−0.0066 (5)
O3	0.0894 (10)	0.0528 (7)	0.0402 (6)	−0.0226 (7)	−0.0035 (6)	−0.0195 (6)
O4	0.0528 (7)	0.0511 (7)	0.0383 (6)	−0.0173 (5)	0.0087 (5)	−0.0143 (5)

C1—O1	1.2116 (19)	C6—C7	1.545 (2)
C1—C2	1.499 (2)	C7—O3	1.2059 (19)
C1—C5	1.526 (2)	C7—C8	1.479 (2)
C2—C3	1.512 (3)	C8—C9	1.384 (2)
C2—H2A	0.9700	C8—C13	1.393 (2)
C2—H2B	0.9700	C9—C10	1.378 (3)
C3—C4	1.528 (3)	C9—H9	0.9300
C3—H3A	0.9700	C10—C11	1.391 (3)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.531 (2)	C11—C12	1.379 (3)
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	C12—C13	1.383 (2)
C5—C6	1.534 (2)	C12—H12	0.9300
C5—H5	0.9800	C13—C14	1.469 (2)
C6—O2	1.4160 (18)	C14—O4	1.2169 (18)
C6—C14	1.536 (2)	O2—H2	0.8200
O1—C1—C2	126.74 (15)	C5—C6—C14	110.99 (12)
O1—C1—C5	124.60 (14)	O2—C6—C7	107.82 (12)
C2—C1—C5	108.66 (13)	C5—C6—C7	113.02 (12)
C1—C2—C3	104.51 (14)	C14—C6—C7	102.49 (12)
C1—C2—H2A	110.9	O3—C7—C8	126.80 (14)
C3—C2—H2A	110.9	O3—C7—C6	125.30 (14)
C1—C2—H2B	110.9	C8—C7—C6	107.89 (13)
C3—C2—H2B	110.9	C9—C8—C13	120.56 (15)
H2A—C2—H2B	108.9	C9—C8—C7	129.09 (15)
C2—C3—C4	103.75 (14)	C13—C8—C7	110.35 (13)
C2—C3—H3A	111.0	C10—C9—C8	118.04 (17)
C4—C3—H3A	111.0	C10—C9—H9	121.0
C2—C3—H3B	111.0	C8—C9—H9	121.0
C4—C3—H3B	111.0	C9—C10—C11	121.33 (16)
H3A—C3—H3B	109.0	C9—C10—H10	119.3
C3—C4—C5	102.74 (13)	C11—C10—H10	119.3
C3—C4—H4A	111.2	C12—C11—C10	120.90 (17)
C5—C4—H4A	111.2	C12—C11—H11	119.6
C3—C4—H4B	111.2	C10—C11—H11	119.6
C5—C4—H4B	111.2	C11—C12—C13	117.90 (17)
H4A—C4—H4B	109.1	C11—C12—H12	121.1
C1—C5—C4	103.78 (13)	C13—C12—H12	121.1
C1—C5—C6	114.77 (12)	C12—C13—C8	121.28 (14)
C4—C5—C6	117.09 (13)	C12—C13—C14	129.02 (15)
C1—C5—H5	106.9	C8—C13—C14	109.69 (14)
C4—C5—H5	106.9	O4—C14—C13	126.49 (15)
C6—C5—H5	106.9	O4—C14—C6	124.45 (13)
O2—C6—C5	111.26 (12)	C13—C14—C6	109.03 (12)
O2—C6—C14	110.92 (12)	C6—O2—H2	109.5
O1—C1—C2—C3	166.12 (15)	O3—C7—C8—C13	173.24 (16)
C5—C1—C2—C3	−13.03 (17)	C6—C7—C8—C13	−5.46 (17)
C1—C2—C3—C4	33.50 (18)	C13—C8—C9—C10	−0.3 (2)
C2—C3—C4—C5	−41.27 (18)	C7—C8—C9—C10	179.19 (16)
O1—C1—C5—C4	168.45 (14)	C8—C9—C10—C11	0.5 (3)
C2—C1—C5—C4	−12.37 (16)	C9—C10—C11—C12	−0.1 (3)
O1—C1—C5—C6	39.4 (2)	C10—C11—C12—C13	−0.5 (3)
C2—C1—C5—C6	−141.39 (14)	C11—C12—C13—C8	0.7 (2)
C3—C4—C5—C1	32.54 (16)	C11—C12—C13—C14	179.53 (15)
C3—C4—C5—C6	160.13 (14)	C9—C8—C13—C12	−0.3 (2)
C1—C5—C6—O2	174.96 (11)	C7—C8—C13—C12	−179.90 (14)
C4—C5—C6—O2	52.92 (18)	C9—C8—C13—C14	−179.32 (14)
C1—C5—C6—C14	−61.01 (16)	C7—C8—C13—C14	1.09 (17)
C4—C5—C6—C14	176.94 (12)	C12—C13—C14—O4	7.0 (3)
C1—C5—C6—C7	53.49 (17)	C8—C13—C14—O4	−174.07 (15)
C4—C5—C6—C7	−68.56 (17)	C12—C13—C14—C6	−175.15 (15)
O2—C6—C7—O3	−54.4 (2)	C8—C13—C14—C6	3.77 (16)
C5—C6—C7—O3	69.0 (2)	O2—C6—C14—O4	56.38 (19)
C14—C6—C7—O3	−171.52 (16)	C5—C6—C14—O4	−67.85 (19)
O2—C6—C7—C8	124.29 (13)	C7—C6—C14—O4	171.22 (14)
C5—C6—C7—C8	−112.31 (14)	O2—C6—C14—C13	−121.51 (13)
C14—C6—C7—C8	7.21 (15)	C5—C6—C14—C13	114.26 (13)
O3—C7—C8—C9	−6.3 (3)	C7—C6—C14—C13	−6.67 (15)
C6—C7—C8—C9	174.99 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4i	0.82	2.09	2.791 (2)	143
C2—H2A···O4ii	0.97	2.60	3.560 (2)	171
C2—H2B···O3iii	0.97	2.58	3.423 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4i	0.82	2.09	2.791 (2)	143

Symmetry code: (i) .