2-Hy­droxy-2-(3-oxobutan-2-yl)indan-1,3-dione

Ghalib, R.M.; Hashim, R.; Mehdi, S.H.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536811020253

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1576

doi:10.1107/S1600536811020253

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2-Hydroxy-2-(3-oxobutan-2-yl)indan-1,3-dione

Raza Murad Ghalib,^a Rokiah Hashim,^a Sayed Hasan Mehdi,^a Chin Sing Yeap ^b ‡ and Hoong-Kun Fun ^b ^*§

^aSchool of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 16 May 2011; accepted 27 May 2011; online 4 June 2011)

In the indane ring system of the title molecule, C₁₃H₁₂O₄, the hydroxy-bearing C atom is 0.134 (1) Å out of the plane of the remaining essentially planar atoms (r.m.s. deviation = 0.010 Å). In the crystal, molecules are linked into chains along the b axis by intermolecular O—H⋯O hydrogen bonds. Additional stabilization is provided by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Fun et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₃H₁₂O₄
M_r = 232.23
Monoclinic, P 2₁ /c
a = 9.5080 (5) Å
b = 6.7200 (4) Å
c = 17.5195 (9) Å
β = 101.044 (1)°
V = 1098.66 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.85 × 0.41 × 0.12 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.917, T_max = 0.988
13885 measured reflections
3796 independent reflections
3243 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.04
3796 reflections
160 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1ⁱ	0.89 (2)	1.90 (2)	2.7880 (13)	171.5 (19)
C12—H12A⋯O3ⁱⁱ	0.96	2.59	3.5416 (17)	173
C12—H12B⋯O3ⁱⁱⁱ	0.96	2.52	3.3215 (16)	142
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020253/lh5255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020253/lh5255Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020253/lh5255Isup3.cml

checkCIF report

Comment top

In the continuation of our studies of ninhydrin reactions with acetone in acidic medium (Fun et al., 2009), we report herein the structure of the title compound (Fig. 1) formed by the reaction of ninhydrin with ethylmethyl ketone in acetic acid. The title compound has potential as a starting material for the synthesis of a large number of complex heterocylic compounds.

In the title compound, the five-membered ring adopts an envelope conformation, with atom C8 forming the flap (Cremer & Pople, 1975). In the indane ring system atom C8 is 0.134 (1)Å out of the plane of the remaining essentially planar atoms. In the crystal structure, the molecules are linked into one-dimensional chains along the b axis (Fig. 2) by intermolecular O2—H1O2···O1ⁱ and weak C12—H12A···O3ⁱⁱⁱ and C12—H12B···O36ⁱⁱⁱ hydrogen bonds (Table 1).

Related literature top

For a related structure, see: Fun et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of ninhydrin (1.78 g) and ethylmethyl ketome (0.90 ml) in molar ratio 1:1 were heated on water bath for 15 minutes in presence of acetic acid. The reaction mixture was dried on rotatory evaporator at low pressure and crystallized with chloroform-n-hexane (1:1) to give the colorless crystals of the title compound (Yield: 100%, mp. 406–408 K).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of title compound, viewed down b axis, showing molecules are linked into one-dimensional chains along the b axis. Hydrogen bonds are shown as dashed lines.

2-Hydroxy-2-(3-oxobutan-2-yl)indan-1,3-dione top

Crystal data top

C₁₃H₁₂O₄	F(000) = 488
M_r = 232.23	D_x = 1.404 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6185 reflections
a = 9.5080 (5) Å	θ = 2.9–32.0°
b = 6.7200 (4) Å	µ = 0.10 mm⁻¹
c = 17.5195 (9) Å	T = 100 K
β = 101.044 (1)°	Plate, yellow
V = 1098.66 (10) Å³	0.85 × 0.41 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3796 independent reflections
Radiation source: fine-focus sealed tube	3243 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 32.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.917, T_max = 0.988	k = −9→9
13885 measured reflections	l = −26→26

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0733P)² + 0.4363P] where P = (F_o² + 2F_c²)/3
3796 reflections	(Δ/σ)_max < 0.001
160 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₃H₁₂O₄	V = 1098.66 (10) Å³
M_r = 232.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5080 (5) Å	µ = 0.10 mm⁻¹
b = 6.7200 (4) Å	T = 100 K
c = 17.5195 (9) Å	0.85 × 0.41 × 0.12 mm
β = 101.044 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3796 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3243 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.988	R_int = 0.025
13885 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.58 e Å⁻³
3796 reflections	Δρ_min = −0.24 e Å⁻³
160 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.41250 (10)	0.29580 (15)	0.22992 (5)	0.0310 (2)
O2	0.52668 (8)	0.59788 (15)	0.12770 (5)	0.0277 (2)
O3	0.25204 (10)	0.81871 (14)	0.05496 (5)	0.0289 (2)
O5	0.11903 (9)	0.36167 (16)	0.09212 (5)	0.0307 (2)
C1	0.23418 (11)	0.75422 (17)	0.18829 (6)	0.0200 (2)
C2	0.15222 (12)	0.90944 (19)	0.20909 (7)	0.0259 (2)
H2A	0.1228	1.0147	0.1753	0.031*
C3	0.11597 (13)	0.9011 (2)	0.28246 (7)	0.0303 (3)
H3A	0.0605	1.0021	0.2978	0.036*
C4	0.16121 (12)	0.7441 (2)	0.33338 (7)	0.0300 (3)
H4A	0.1365	0.7431	0.3822	0.036*
C5	0.24275 (12)	0.5891 (2)	0.31218 (6)	0.0257 (2)
H5A	0.2725	0.4839	0.3459	0.031*
C6	0.27822 (10)	0.59662 (17)	0.23882 (6)	0.0202 (2)
C7	0.36157 (11)	0.45130 (17)	0.20197 (6)	0.0213 (2)
C8	0.38181 (10)	0.53665 (17)	0.12305 (6)	0.01995 (19)
C9	0.28310 (11)	0.72095 (17)	0.11399 (6)	0.0202 (2)
C10	0.34388 (11)	0.40003 (17)	0.05236 (6)	0.0207 (2)
H10A	0.3536	0.4786	0.0065	0.025*
C11	0.18853 (11)	0.33382 (17)	0.04139 (6)	0.0219 (2)
C12	0.12393 (14)	0.2357 (2)	−0.03389 (7)	0.0300 (3)
H12A	0.0215	0.2329	−0.0393	0.045*
H12B	0.1596	0.1022	−0.0344	0.045*
H12C	0.1493	0.3092	−0.0763	0.045*
C13	0.44326 (12)	0.22016 (19)	0.05498 (7)	0.0273 (2)
H13A	0.4215	0.1502	0.0064	0.041*
H13B	0.4296	0.1329	0.0964	0.041*
H13C	0.5410	0.2645	0.0639	0.041*
H1O2	0.554 (2)	0.666 (3)	0.1717 (12)	0.044 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0329 (4)	0.0318 (5)	0.0278 (4)	0.0113 (4)	0.0045 (3)	0.0083 (4)
O2	0.0169 (3)	0.0390 (5)	0.0272 (4)	−0.0056 (3)	0.0039 (3)	−0.0064 (4)
O3	0.0332 (4)	0.0278 (4)	0.0256 (4)	0.0009 (4)	0.0059 (3)	0.0069 (3)
O5	0.0240 (4)	0.0371 (5)	0.0319 (4)	−0.0074 (4)	0.0076 (3)	−0.0081 (4)
C1	0.0179 (4)	0.0210 (5)	0.0206 (4)	−0.0004 (3)	0.0026 (3)	−0.0012 (4)
C2	0.0239 (5)	0.0240 (5)	0.0286 (5)	0.0030 (4)	0.0021 (4)	−0.0044 (4)
C3	0.0238 (5)	0.0358 (7)	0.0311 (5)	0.0033 (5)	0.0047 (4)	−0.0116 (5)
C4	0.0228 (5)	0.0438 (7)	0.0239 (5)	−0.0012 (5)	0.0061 (4)	−0.0068 (5)
C5	0.0220 (4)	0.0351 (6)	0.0199 (4)	−0.0018 (4)	0.0035 (3)	0.0008 (4)
C6	0.0168 (4)	0.0238 (5)	0.0194 (4)	−0.0005 (4)	0.0019 (3)	0.0000 (4)
C7	0.0181 (4)	0.0238 (5)	0.0210 (4)	0.0016 (4)	0.0013 (3)	0.0014 (4)
C8	0.0163 (4)	0.0227 (5)	0.0207 (4)	0.0000 (4)	0.0031 (3)	−0.0008 (4)
C9	0.0191 (4)	0.0199 (5)	0.0213 (4)	−0.0023 (3)	0.0031 (3)	0.0001 (4)
C10	0.0196 (4)	0.0220 (5)	0.0206 (4)	0.0000 (4)	0.0044 (3)	−0.0001 (4)
C11	0.0203 (4)	0.0200 (5)	0.0239 (4)	0.0011 (4)	0.0003 (3)	−0.0009 (4)
C12	0.0292 (5)	0.0312 (6)	0.0256 (5)	0.0000 (5)	−0.0046 (4)	−0.0044 (5)
C13	0.0232 (5)	0.0265 (6)	0.0323 (5)	0.0031 (4)	0.0057 (4)	−0.0021 (4)

Geometric parameters (Å, º) top

O1—C7	1.2147 (14)	C5—H5A	0.9300
O2—C8	1.4249 (12)	C6—C7	1.4815 (15)
O2—H1O2	0.89 (2)	C7—C8	1.5425 (15)
O3—C9	1.2129 (13)	C8—C10	1.5283 (15)
O5—C11	1.2193 (14)	C8—C9	1.5436 (15)
C1—C2	1.3917 (16)	C10—C11	1.5192 (15)
C1—C6	1.3924 (15)	C10—C13	1.5294 (16)
C1—C9	1.4808 (14)	C10—H10A	0.9800
C2—C3	1.3941 (17)	C11—C12	1.4969 (15)
C2—H2A	0.9300	C12—H12A	0.9600
C3—C4	1.395 (2)	C12—H12B	0.9600
C3—H3A	0.9300	C12—H12C	0.9600
C4—C5	1.3908 (18)	C13—H13A	0.9600
C4—H4A	0.9300	C13—H13B	0.9600
C5—C6	1.3906 (14)	C13—H13C	0.9600

C8—O2—H1O2	108.3 (13)	C10—C8—C9	110.74 (8)
C2—C1—C6	121.25 (10)	C7—C8—C9	102.29 (8)
C2—C1—C9	129.00 (10)	O3—C9—C1	126.98 (10)
C6—C1—C9	109.71 (9)	O3—C9—C8	124.49 (10)
C1—C2—C3	117.45 (11)	C1—C9—C8	108.53 (9)
C1—C2—H2A	121.3	C11—C10—C8	110.56 (8)
C3—C2—H2A	121.3	C11—C10—C13	110.64 (9)
C2—C3—C4	121.30 (11)	C8—C10—C13	113.70 (9)
C2—C3—H3A	119.3	C11—C10—H10A	107.2
C4—C3—H3A	119.3	C8—C10—H10A	107.2
C5—C4—C3	120.98 (11)	C13—C10—H10A	107.2
C5—C4—H4A	119.5	O5—C11—C12	121.44 (10)
C3—C4—H4A	119.5	O5—C11—C10	120.83 (10)
C6—C5—C4	117.77 (11)	C12—C11—C10	117.73 (10)
C6—C5—H5A	121.1	C11—C12—H12A	109.5
C4—C5—H5A	121.1	C11—C12—H12B	109.5
C5—C6—C1	121.24 (10)	H12A—C12—H12B	109.5
C5—C6—C7	128.57 (10)	C11—C12—H12C	109.5
C1—C6—C7	110.18 (9)	H12A—C12—H12C	109.5
O1—C7—C6	126.63 (10)	H12B—C12—H12C	109.5
O1—C7—C8	124.94 (10)	C10—C13—H13A	109.5
C6—C7—C8	108.34 (9)	C10—C13—H13B	109.5
O2—C8—C10	107.17 (8)	H13A—C13—H13B	109.5
O2—C8—C7	109.96 (8)	C10—C13—H13C	109.5
C10—C8—C7	116.90 (9)	H13A—C13—H13C	109.5
O2—C8—C9	109.65 (9)	H13B—C13—H13C	109.5

C6—C1—C2—C3	0.02 (17)	C2—C1—C9—O3	−5.20 (19)
C9—C1—C2—C3	177.51 (11)	C6—C1—C9—O3	172.52 (11)
C1—C2—C3—C4	0.58 (18)	C2—C1—C9—C8	175.17 (11)
C2—C3—C4—C5	−0.79 (19)	C6—C1—C9—C8	−7.10 (12)
C3—C4—C5—C6	0.37 (18)	O2—C8—C9—O3	73.28 (13)
C4—C5—C6—C1	0.22 (16)	C10—C8—C9—O3	−44.77 (14)
C4—C5—C6—C7	−179.24 (11)	C7—C8—C9—O3	−170.06 (10)
C2—C1—C6—C5	−0.43 (16)	O2—C8—C9—C1	−107.08 (9)
C9—C1—C6—C5	−178.36 (10)	C10—C8—C9—C1	134.86 (9)
C2—C1—C6—C7	179.12 (10)	C7—C8—C9—C1	9.58 (11)
C9—C1—C6—C7	1.19 (12)	O2—C8—C10—C11	−177.89 (9)
C5—C6—C7—O1	1.15 (19)	C7—C8—C10—C11	58.23 (12)
C1—C6—C7—O1	−178.35 (11)	C9—C8—C10—C11	−58.34 (11)
C5—C6—C7—C8	−175.32 (10)	O2—C8—C10—C13	56.96 (12)
C1—C6—C7—C8	5.18 (12)	C7—C8—C10—C13	−66.92 (12)
O1—C7—C8—O2	−68.98 (14)	C9—C8—C10—C13	176.52 (9)
C6—C7—C8—O2	107.57 (10)	C8—C10—C11—O5	−12.09 (15)
O1—C7—C8—C10	53.47 (14)	C13—C10—C11—O5	114.77 (12)
C6—C7—C8—C10	−129.99 (9)	C8—C10—C11—C12	167.27 (10)
O1—C7—C8—C9	174.59 (11)	C13—C10—C11—C12	−65.87 (13)
C6—C7—C8—C9	−8.87 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1ⁱ	0.89 (2)	1.90 (2)	2.7880 (13)	171.5 (19)
C12—H12A···O3ⁱⁱ	0.96	2.59	3.5416 (17)	173
C12—H12B···O3ⁱⁱⁱ	0.96	2.52	3.3215 (16)	142

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂O₄
M_r	232.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.5080 (5), 6.7200 (4), 17.5195 (9)
β (°)	101.044 (1)
V (Å³)	1098.66 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.85 × 0.41 × 0.12

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.917, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	13885, 3796, 3243
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.747

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.04
No. of reflections	3796
No. of parameters	160
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1ⁱ	0.89 (2)	1.90 (2)	2.7880 (13)	171.5 (19)
C12—H12A···O3ⁱⁱ	0.96	2.59	3.5416 (17)	173
C12—H12B···O3ⁱⁱⁱ	0.96	2.52	3.3215 (16)	142

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

Footnotes

‡Thomson Reuters ResearcherID: A-5523-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

RMG, RH and SHM would like to acknowledge Universiti Sains Malaysia (USM) for the University Grant 1001/PTEKIND/8140152. HKF and CSY also thank USM for the Research University Grant 1001/PFIZIK/811160.

References

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