2-Acetonyl-2-hydroxy-indan-1,3-dione.

In the title compound, C(12)H(10)O(4), the five-membered ring adopts an envelope conformation, with the Csp(3) atom at the flap [deviation = 0.145 (2) Å]. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the activities and applications of ninhydrin derivatives, see: Ruhemann (1910 ▶); Kaiser et al. (1970 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H10O4

M = 218.20

Orthorhombic,

a = 18.1190 (2) Å

b = 8.8135 (1) Å

c = 6.2585 (1) Å

V = 999.43 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.29 × 0.19 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.969, T max = 0.992

14417 measured reflections

1818 independent reflections

1720 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.106

S = 1.18

1818 reflections

150 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016067/ci2791sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016067/ci2791Isup2.hkl

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

C12H10O4	F(000) = 456
Mr = 218.20	Dx = 1.450 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5199 reflections
a = 18.1190 (2) Å	θ = 3.2–31.5°
b = 8.8135 (1) Å	µ = 0.11 mm−1
c = 6.2585 (1) Å	T = 100 K
V = 999.43 (2) Å3	Plate, yellow
Z = 4	0.29 × 0.19 × 0.08 mm

Bruker SMART APEXII CCD area-detector diffractometer	1818 independent reflections
Radiation source: fine-focus sealed tube	1720 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 31.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −26→26
Tmin = 0.969, Tmax = 0.992	k = −12→13
14417 measured reflections	l = −9→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ2(Fo2) + (0.0696P)2 + 0.0468P] where P = (Fo2 + 2Fc2)/3
1818 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 0.42 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.13189 (7)	0.07160 (14)	0.5143 (2)	0.0217 (3)
O2	0.21514 (6)	0.36656 (13)	1.0967 (2)	0.0158 (2)
O3	0.27231 (6)	0.16183 (13)	0.7536 (2)	0.0153 (2)
O4	0.06202 (6)	0.15803 (14)	1.0224 (2)	0.0165 (3)
C1	0.14680 (8)	0.17868 (17)	0.6278 (3)	0.0130 (3)
C2	0.12208 (8)	0.33840 (16)	0.6024 (3)	0.0121 (3)
C3	0.07836 (8)	0.40053 (18)	0.4425 (3)	0.0145 (3)
H3A	0.0609	0.3415	0.3301	0.017*
C4	0.06148 (8)	0.55486 (19)	0.4566 (3)	0.0161 (3)
H4A	0.0314	0.5991	0.3535	0.019*
C5	0.08914 (9)	0.64417 (18)	0.6239 (3)	0.0163 (3)
H5A	0.0784	0.7473	0.6273	0.020*
C6	0.13236 (8)	0.58104 (17)	0.7850 (3)	0.0144 (3)
H6A	0.1502	0.6401	0.8967	0.017*
C7	0.14801 (8)	0.42619 (16)	0.7731 (3)	0.0115 (3)
C8	0.18969 (8)	0.32969 (16)	0.9244 (3)	0.0115 (3)
C9	0.19764 (8)	0.17061 (16)	0.8252 (3)	0.0107 (3)
C10	0.17882 (8)	0.04091 (17)	0.9758 (3)	0.0125 (3)
H10A	0.1889	−0.0547	0.9049	0.015*
H10B	0.2103	0.0470	1.1008	0.015*
C11	0.09891 (8)	0.04343 (17)	1.0464 (3)	0.0121 (3)
C12	0.06798 (9)	−0.10028 (18)	1.1373 (3)	0.0173 (3)
H12A	0.0295	−0.0763	1.2371	0.026*
H12B	0.1064	−0.1552	1.2092	0.026*
H12C	0.0482	−0.1614	1.0240	0.026*
H1O3	0.2777 (12)	0.069 (3)	0.713 (5)	0.029 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0303 (6)	0.0148 (5)	0.0200 (6)	0.0013 (4)	−0.0085 (5)	−0.0058 (5)
O2	0.0176 (5)	0.0137 (5)	0.0161 (6)	0.0002 (4)	−0.0044 (5)	−0.0035 (4)
O3	0.0116 (5)	0.0132 (5)	0.0211 (6)	0.0002 (4)	0.0044 (5)	−0.0038 (4)
O4	0.0150 (5)	0.0170 (5)	0.0174 (6)	0.0032 (4)	0.0002 (5)	−0.0008 (5)
C1	0.0142 (6)	0.0114 (6)	0.0133 (7)	−0.0005 (5)	−0.0010 (6)	−0.0014 (5)
C2	0.0127 (6)	0.0113 (6)	0.0124 (7)	0.0001 (4)	0.0006 (5)	−0.0010 (5)
C3	0.0153 (6)	0.0160 (7)	0.0123 (7)	−0.0008 (5)	−0.0012 (6)	0.0003 (6)
C4	0.0159 (6)	0.0167 (7)	0.0156 (7)	0.0019 (5)	−0.0010 (6)	0.0044 (6)
C5	0.0182 (6)	0.0127 (6)	0.0181 (8)	0.0030 (5)	0.0002 (6)	0.0011 (6)
C6	0.0156 (6)	0.0111 (6)	0.0165 (7)	0.0012 (5)	−0.0008 (6)	−0.0022 (6)
C7	0.0119 (6)	0.0105 (6)	0.0122 (7)	0.0004 (4)	0.0004 (5)	0.0000 (5)
C8	0.0095 (5)	0.0114 (6)	0.0135 (7)	−0.0011 (5)	0.0002 (5)	−0.0017 (5)
C9	0.0097 (5)	0.0099 (6)	0.0125 (6)	0.0008 (4)	0.0002 (5)	−0.0016 (5)
C10	0.0117 (6)	0.0106 (6)	0.0152 (7)	0.0008 (4)	0.0009 (5)	0.0006 (5)
C11	0.0125 (6)	0.0142 (6)	0.0097 (6)	−0.0006 (5)	−0.0007 (5)	−0.0019 (5)
C12	0.0177 (7)	0.0147 (7)	0.0195 (8)	−0.0027 (5)	0.0039 (6)	−0.0004 (6)

O1—C1	1.212 (2)	C5—H5A	0.93
O2—C8	1.217 (2)	C6—C7	1.396 (2)
O3—C9	1.4273 (17)	C6—H6A	0.93
O3—H1O3	0.86 (3)	C7—C8	1.480 (2)
O4—C11	1.2205 (19)	C8—C9	1.540 (2)
C1—C2	1.486 (2)	C9—C10	1.521 (2)
C1—C9	1.542 (2)	C10—C11	1.514 (2)
C2—C3	1.389 (2)	C10—H10A	0.97
C2—C7	1.400 (2)	C10—H10B	0.97
C3—C4	1.397 (2)	C11—C12	1.498 (2)
C3—H3A	0.93	C12—H12A	0.96
C4—C5	1.402 (2)	C12—H12B	0.96
C4—H4A	0.93	C12—H12C	0.96
C5—C6	1.393 (2)
C9—O3—H1O3	104.5 (16)	O2—C8—C9	124.39 (14)
O1—C1—C2	127.44 (16)	C7—C8—C9	108.24 (14)
O1—C1—C9	124.53 (14)	O3—C9—C10	111.50 (12)
C2—C1—C9	108.02 (12)	O3—C9—C8	105.33 (11)
C3—C2—C7	121.55 (13)	C10—C9—C8	114.42 (14)
C3—C2—C1	128.51 (15)	O3—C9—C1	108.50 (13)
C7—C2—C1	109.92 (14)	C10—C9—C1	113.41 (12)
C2—C3—C4	117.60 (15)	C8—C9—C1	103.00 (12)
C2—C3—H3A	121.2	C11—C10—C9	112.60 (12)
C4—C3—H3A	121.2	C11—C10—H10A	109.1
C3—C4—C5	121.03 (15)	C9—C10—H10A	109.1
C3—C4—H4A	119.5	C11—C10—H10B	109.1
C5—C4—H4A	119.5	C9—C10—H10B	109.1
C6—C5—C4	121.14 (14)	H10A—C10—H10B	107.8
C6—C5—H5A	119.4	O4—C11—C12	122.79 (14)
C4—C5—H5A	119.4	O4—C11—C10	120.01 (14)
C5—C6—C7	117.80 (15)	C12—C11—C10	117.16 (13)
C5—C6—H6A	121.1	C11—C12—H12A	109.5
C7—C6—H6A	121.1	C11—C12—H12B	109.5
C6—C7—C2	120.84 (15)	H12A—C12—H12B	109.5
C6—C7—C8	129.16 (15)	C11—C12—H12C	109.5
C2—C7—C8	109.98 (13)	H12A—C12—H12C	109.5
O2—C8—C7	127.35 (14)	H12B—C12—H12C	109.5
O1—C1—C2—C3	−1.6 (3)	C2—C7—C8—C9	6.84 (16)
C9—C1—C2—C3	177.10 (15)	O2—C8—C9—O3	−74.26 (18)
O1—C1—C2—C7	176.83 (17)	C7—C8—C9—O3	104.64 (14)
C9—C1—C2—C7	−4.49 (17)	O2—C8—C9—C10	48.55 (19)
C7—C2—C3—C4	0.5 (2)	C7—C8—C9—C10	−132.56 (13)
C1—C2—C3—C4	178.78 (15)	O2—C8—C9—C1	172.10 (14)
C2—C3—C4—C5	1.4 (2)	C7—C8—C9—C1	−9.00 (15)
C3—C4—C5—C6	−2.1 (3)	O1—C1—C9—O3	75.56 (19)
C4—C5—C6—C7	0.8 (2)	C2—C1—C9—O3	−103.16 (14)
C5—C6—C7—C2	1.1 (2)	O1—C1—C9—C10	−48.9 (2)
C5—C6—C7—C8	−177.55 (15)	C2—C1—C9—C10	132.37 (13)
C3—C2—C7—C6	−1.8 (2)	O1—C1—C9—C8	−173.13 (16)
C1—C2—C7—C6	179.63 (14)	C2—C1—C9—C8	8.15 (16)
C3—C2—C7—C8	177.09 (14)	O3—C9—C10—C11	−177.41 (13)
C1—C2—C7—C8	−1.45 (17)	C8—C9—C10—C11	63.19 (17)
C6—C7—C8—O2	4.5 (3)	C1—C9—C10—C11	−54.58 (17)
C2—C7—C8—O2	−174.31 (15)	C9—C10—C11—O4	−16.2 (2)
C6—C7—C8—C9	−174.36 (15)	C9—C10—C11—C12	161.75 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O2i	0.86 (3)	1.93 (3)	2.7907 (16)	174 (3)
C3—H3A···O4ii	0.93	2.51	3.401 (2)	159
C12—H12A···O4iii	0.96	2.54	3.408 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O2i	0.86 (3)	1.93 (3)	2.7907 (16)	174 (3)
C3—H3A⋯O4ii	0.93	2.51	3.401 (2)	159
C12—H12A⋯O4iii	0.96	2.54	3.408 (2)	150

Symmetry codes: (i) ; (ii) ; (iii) .