rac-2-Hy­droxy-2-(2-oxocyclo­pent­yl)-1H-indene-1,3(2H)-dione

Sundar, J.K.; Maharani, S.; Kumar, R.R.; Natarajan, S.; Suresh, J.; Lakshman, P.L.N.

doi:10.1107/S1600536810042856

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2967

https://doi.org/10.1107/S1600536810042856

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rac-2-Hydroxy-2-(2-oxocyclopentyl)-1H-indene-1,3(2H)-dione

J. Kalyana Sundar,^a S. Maharani,^b R. Ranjith Kumar,^b S. Natarajan,^a J. Suresh ^c and P. L. Nilantha Lakshman ^d ^*

^aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, ^cDepartment of Physics, The Madura College, Madurai 625 011, India, and ^dDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 16 September 2010; accepted 21 October 2010; online 30 October 2010)

In the title compound, C₁₄H₁₂O₄, the indene unit is essentially planar [r.m.s. deviation = 0.0309 (1) Å] and the cyclopentanone ring adopts a twist form. In the crystal, molecules 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_r = 244.24
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.104
S = 1.07
2054 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) -x, -y, -z+1.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042856/gk2301Isup2.hkl

checkCIF report

Comment top

Ninhydrin derivatives constitute a versatile class of compounds with profound biological activities such as antibacterial, anticonvulsant, anticancer and anti-inflammatory activities. The present work constitutes the synthesis of various ninhydrin derivatives which are being tested for anti-tubercular and other biological activities.

Related literature top

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

Experimental top

A mixture of cyclopentanone (0.5 g, 0.006 mol) and ninhydrin (1.05 g, 0.006 mol) in methanol (10 ml) was heated under reflux for 4 h in the presence of solid sodium ethoxide (0.4 g, 0.006 mol). After completion of the reaction, as was evident from TLC, the reaction mixture was poured into crushed ice, extracted with dichloromethane and subjected to column chromatographic purification using petroleum ether:ethyl acetate mixture (90:10 v/v) to obtain the product in 50% yield. The compound was further recrystallized from ethyl acetate to obtain suitable crystals for X-ray studies (m.p. 543 K)

Structure description top

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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing diagram of the title compound.

rac-2-Hydroxy-2-(2-oxocyclopentyl)-1H-indene-1,3(2H)-dione top

Crystal data top

C₁₄H₁₂O₄	Z = 2
M_r = 244.24	F(000) = 256
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0487P)² + 0.2034P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2054 reflections	Δρ_max = 0.25 e Å⁻³
164 parameters	Δρ_min = −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)

Crystal data top

C₁₄H₁₂O₄	γ = 68.50 (3)°
M_r = 244.24	V = 586.1 (4) Å³
Triclinic, P1	Z = 2
a = 8.044 (3) Å	Mo Kα radiation
b = 8.404 (4) Å	µ = 0.10 mm⁻¹
c = 10.239 (3) Å	T = 293 K
α = 66.95 (3)°	0.26 × 0.22 × 0.19 mm
β = 74.36 (2)°

Data collection top

Nonius MACH3 diffractometer	1886 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.016
T_min = 0.974, T_max = 0.981	3 standard reflections every 60 min
2534 measured reflections	intensity decay: none
2054 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	Δρ_max = 0.25 e Å⁻³
2054 reflections	Δρ_min = −0.23 e Å⁻³
164 parameters

Special details top

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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂O₄
M_r	244.24
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.044 (3), 8.404 (4), 10.239 (3)
α, β, γ (°)	66.95 (3), 74.36 (2), 68.50 (3)
V (Å³)	586.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.26 × 0.22 × 0.19

Data collection
Diffractometer	Nonius MACH3
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.974, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	2534, 2054, 1886
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.07
No. of reflections	2054
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1.

Acknowledgements

JKS thanks the UGC for an RFSMS fellowship.

References

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