1,2-Dihydr­oxy-2-(3-methyl­but-2-en­yl)-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid monohydrate

Franscisco, A.I.; Silveira, G. de Q.; Resende, J.A.L.C.; Balliano, T.L.; Malta, V.R.S.; Pinto, A.V.

doi:10.1107/S1600536810000516

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o341

https://doi.org/10.1107/S1600536810000516

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1,2-Dihydroxy-2-(3-methylbut-2-enyl)-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid monohydrate

Acácio Ivo Franscisco,^a Gleiciani de Q. Silveira,^a Jackson A. L. C. Resende,^a Tatiane L. Balliano,^b Valéria R. S. Malta ^b ^* and Antonio Ventura Pinto ^c

^aInstituto de Química, Universidade Federal Fluminense, Centro, CEP 24020-150, Niterói, RJ, Brazil, ^bInstituto de Química e Biotecnologia, Universidade Federal de Alagoas, CEP 57072-970, Maceió, Al, Brazil, and ^cNúcleo de Pesquisas em Produtos Naturais, Universidade Federal do Rio de Janeiro, Ilha do Fundão, CEP 21944-971, Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: vrsm@qui.ufal.br

(Received 3 December 2009; accepted 5 January 2010; online 13 January 2010)

The title compound, C₁₅H₁₆O₅·H₂O, is an intermediate of the Hooker oxidation reaction, used for the synthesis of 2-hydroxy-3-(2-methylprop-1-enyl)naphthalene-1,4-dione (nor-lapachol). The packing in the crystal structure is arranged by an O—H⋯O hydrogen-bonded network along the [100] and [010] directions. Each organic molecule is linked to four other molecules via the hydroxy groups. The water solvent molecule is connected to carboxylic acid groups by three hydrogen bonds.

Related literature

For a related structure, see Cunningham et al. (1999 ). For information on the mechanism of the Hooker oxidation reaction, see: Hooker (1936 ); Hooker & Steyermark (1936 ); Fieser & Fieser, (1948 ); Fieser & Bader (1951 ); Fieser et al. (1936 ); Lee et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₆O₅·H₂O
M_r = 294.29
Monoclinic, P 2₁
a = 9.5514 (7) Å
b = 5.7762 (5) Å
c = 13.1324 (9) Å
β = 92.126 (12)°
V = 724.03 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.21 × 0.15 × 0.09 mm

Data collection

Enraf–Nonius FR590 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.991
18985 measured reflections
1827 independent reflections
1490 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.093
S = 1.06
1827 reflections
195 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.93	2.729 (2)	166
O2—H2⋯O1ⁱⁱ	0.82	2.08	2.846 (2)	155
O4—H4⋯O1Wⁱⁱ	0.82	1.72	2.520 (3)	164
O1W—H1B⋯O5ⁱⁱⁱ	0.84	1.96	2.785 (3)	167
O1W—H1A⋯O5	0.84	2.05	2.884 (3)	173
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z]$ ; (ii) x, y-1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Data collection: COLLECT (Nonius, 2004 ); cell refinement: DIRAX/LSQ (Duisenberg, 1992 ); data reduction: EVALCCD (Duisenberg et al., 2003 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae, 2006 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810000516/lh2966sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000516/lh2966Isup2.hkl

checkCIF report

Comment top

For many years investigations on the Hooker intermediate were object of preparation of nor-lapachol (Fieser et al., 1936), principally due to the different oxidation mechanism (Lee et al., 1995) in which the substrate 2-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione) (lapachol) undergoes rearrangement into nor-lapachol (Fieser et al., 1951). This Hooker oxidation reaction is applicable to a large number of hydroxynaphthoquinones with side chains in the quinone ring (Hooker, 1936; Hooker & Steyermark, 1936).

Although spectroscopic data (NMR and elemental analysis) has indicated (Fieser et al., 1948) the likely structure of the intermediate, X-ray diffraction study has never been performed. We report herein the synthesis and the crystal structure of the title compound, (I). An ORTEP-3 (Farrugia, 1997) drawing of (I) is shown in Fig. 1, and selected geometric parameters are presented in Table 1. The five-membered ring adopts an envelope conformation [q2 = 0.260 (2) Å e φ2 = -147.3 (5)°]. The ring is stretched and this is reflected in the larger bond length of C1—C2, like in the oxoindane ester methyl trans-2-(trans-4-tert-butylcyclohexyl)methyl-2,3-dihydroxy- 1-oxoindan-3-carboxylate (Cunningham et al., 1999). The crystal packing is stabilized by five hydrogen bonds (Table 1) forming a hydrogen-bonded network along the [010] and [100] directions (Figure 2).

Related literature top

For a related structure, see Cunningham et al. (1999). For information on the mechanism of the Hooker oxidation reaction, see: Hooker (1936); Hooker & Steyermark (1936); Fieser & Fieser, (1948); Fieser & Bader (1951); Fieser et al. (1936); Lee et al. (1995).

Experimental top

Lapachol (10.0 g, 41.3 mmol) in THF (70 ml) was added to a solution of Na₂CO₃ (4.8 g, 45.3 mmol) in water (100 ml). The mixture was refluxed under N₂ and when the temperature reached 316K , H₂O₂ (32 ml) was added. The reaction mixture remained under reflux for one hour and after this period it was cooled to 283K. Then conc. HCl was added until appearance of a white precipitate, which was filtered under vaccum [yield; 81%, 493-494K, lit. (Fieser et al., 1951): 492-493K].

Structure description top

For a related structure, see Cunningham et al. (1999). For information on the mechanism of the Hooker oxidation reaction, see: Hooker (1936); Hooker & Steyermark (1936); Fieser & Fieser, (1948); Fieser & Bader (1951); Fieser et al. (1936); Lee et al. (1995).

Computing details top

Data collection: COLLECT (Nonius, 2004); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae, 2006) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. : The molecular structure of (I) with displacement ellipsoids are drawn at the 50% probability level. A hydrogen bond is shown as a dashed line.
	Fig. 2. : A packing diagram of (I) (Macrae et al., 2006). Hydrogen bonds are shown as dotted lines.

1,2-Dihydroxy-2-(3-methylbut-2-enyl)-3-oxo-2,3-dihydro-1H-indene-1- carboxylic acid monohydrate top

Crystal data top

C₁₅H₁₆O₅·H₂O	F(000) = 312
M_r = 294.29	D_x = 1.357 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 18985 reflections
a = 9.5514 (7) Å	θ = 3.1–27.5°
b = 5.7762 (5) Å	µ = 0.11 mm⁻¹
c = 13.1324 (9) Å	T = 298 K
β = 92.126 (12)°	Prism, colourless
V = 724.03 (10) Å³	0.21 × 0.15 × 0.09 mm
Z = 2

Data collection top

Enraf–Nonius FR590 diffractometer	1490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
CCD rotation images, thick slices scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.981, T_max = 0.991	k = −7→7
18985 measured reflections	l = −17→17
1827 independent reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0546P)²] where P = (F_o² + 2F_c²)/3
1827 reflections	(Δ/σ)_max = 0.029
195 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₆O₅·H₂O	V = 724.03 (10) Å³
M_r = 294.29	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.5514 (7) Å	µ = 0.11 mm⁻¹
b = 5.7762 (5) Å	T = 298 K
c = 13.1324 (9) Å	0.21 × 0.15 × 0.09 mm
β = 92.126 (12)°

Data collection top

Enraf–Nonius FR590 diffractometer	1827 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1490 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.991	R_int = 0.034
18985 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.093	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
1827 reflections	Δρ_min = −0.17 e Å⁻³
195 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
O1W	0.5721 (2)	0.8481 (4)	0.0536 (2)	0.0823 (9)
H1A	0.6162	0.7243	0.0448	0.123*
H1B	0.4867	0.8512	0.0372	0.123*
O1	0.90465 (17)	0.6665 (3)	0.10377 (11)	0.0322 (4)
H1	0.9157	0.6392	0.0433	0.048*
O2	1.01902 (18)	0.1204 (3)	0.09344 (12)	0.0334 (4)
H2	0.9917	−0.0037	0.1157	0.05*
O3	1.03440 (19)	0.0001 (3)	0.30071 (13)	0.0403 (4)
O4	0.73158 (19)	0.1340 (3)	0.14502 (13)	0.0407 (4)
H4	0.6744	0.0621	0.1092	0.061*
O5	0.7005 (2)	0.4019 (3)	0.02549 (15)	0.0484 (5)
C1	0.8810 (2)	0.4586 (4)	0.15549 (16)	0.0268 (5)
C2	1.0096 (2)	0.2926 (4)	0.16956 (16)	0.0281 (5)
C3	0.9894 (2)	0.1855 (4)	0.27440 (16)	0.0283 (5)
C4	0.9048 (2)	0.3500 (4)	0.33153 (16)	0.0288 (5)
C5	0.8816 (2)	0.3586 (5)	0.43499 (17)	0.0375 (6)
H5	0.9206	0.2491	0.4795	0.045*
C6	0.7988 (3)	0.5348 (5)	0.46952 (18)	0.0411 (6)
H6	0.7827	0.5462	0.5387	0.049*
C7	0.7396 (3)	0.6945 (5)	0.40303 (18)	0.0411 (6)
H7	0.6842	0.8122	0.4282	0.049*
C8	0.7608 (2)	0.6834 (5)	0.29942 (17)	0.0349 (5)
H8	0.7197	0.7907	0.2548	0.042*
C9	0.8446 (2)	0.5086 (4)	0.26450 (16)	0.0270 (5)
C10	0.7606 (2)	0.3286 (4)	0.10134 (17)	0.0282 (5)
C11	1.1452 (2)	0.4353 (5)	0.1714 (2)	0.0373 (6)
H11A	1.1624	0.4881	0.1029	0.045*
H11B	1.1333	0.5709	0.2138	0.045*
C12	1.2692 (3)	0.3023 (5)	0.2109 (2)	0.0428 (6)
H12	1.2888	0.1649	0.1774	0.051*
C13	1.3534 (3)	0.3581 (5)	0.2876 (2)	0.0420 (6)
C14	1.4737 (3)	0.2069 (7)	0.3225 (3)	0.0626 (9)
H14A	1.4621	0.1623	0.3921	0.094*
H14B	1.5599	0.2908	0.3172	0.094*
H14C	1.476	0.0711	0.2805	0.094*
C15	1.3374 (4)	0.5712 (7)	0.3500 (3)	0.0759 (11)
H15A	1.3521	0.5339	0.4208	0.114*
H15B	1.2447	0.6326	0.3387	0.114*
H15C	1.405	0.6844	0.3307	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.0610 (13)	0.0400 (13)	0.142 (2)	0.0055 (11)	−0.0517 (14)	−0.0227 (15)
O1	0.0497 (9)	0.0228 (9)	0.0242 (7)	−0.0045 (7)	0.0027 (7)	0.0025 (7)
O2	0.0465 (10)	0.0265 (9)	0.0274 (8)	−0.0033 (7)	0.0040 (7)	−0.0043 (7)
O3	0.0463 (10)	0.0360 (10)	0.0382 (10)	0.0086 (8)	−0.0046 (8)	0.0069 (9)
O4	0.0463 (10)	0.0323 (10)	0.0424 (10)	−0.0122 (8)	−0.0154 (7)	0.0085 (9)
O5	0.0588 (11)	0.0386 (11)	0.0458 (11)	−0.0091 (9)	−0.0246 (9)	0.0103 (8)
C1	0.0341 (12)	0.0224 (12)	0.0238 (11)	−0.0019 (9)	0.0006 (9)	0.0017 (9)
C2	0.0334 (11)	0.0246 (11)	0.0263 (11)	−0.0016 (9)	0.0003 (9)	−0.0041 (9)
C3	0.0289 (10)	0.0303 (13)	0.0252 (10)	−0.0023 (10)	−0.0065 (8)	0.0000 (10)
C4	0.0283 (11)	0.0315 (12)	0.0263 (11)	−0.0018 (10)	−0.0027 (9)	0.0004 (10)
C5	0.0386 (12)	0.0475 (16)	0.0259 (11)	0.0041 (12)	−0.0033 (10)	0.0052 (11)
C6	0.0414 (14)	0.0581 (18)	0.0241 (12)	−0.0001 (13)	0.0034 (11)	−0.0045 (12)
C7	0.0426 (13)	0.0433 (15)	0.0380 (13)	0.0036 (12)	0.0089 (11)	−0.0046 (13)
C8	0.0422 (12)	0.0297 (13)	0.0327 (12)	0.0013 (11)	0.0014 (10)	0.0017 (11)
C9	0.0307 (11)	0.0248 (11)	0.0256 (11)	−0.0052 (9)	0.0009 (9)	−0.0005 (9)
C10	0.0349 (11)	0.0226 (12)	0.0269 (11)	0.0015 (9)	−0.0010 (9)	0.0005 (9)
C11	0.0329 (12)	0.0359 (14)	0.0434 (14)	−0.0057 (10)	0.0037 (11)	−0.0034 (11)
C12	0.0330 (12)	0.0399 (15)	0.0558 (16)	−0.0009 (11)	0.0083 (12)	−0.0098 (13)
C13	0.0336 (12)	0.0421 (15)	0.0503 (15)	−0.0053 (12)	0.0028 (11)	0.0000 (13)
C14	0.0361 (14)	0.066 (2)	0.085 (2)	−0.0035 (15)	−0.0045 (14)	0.0077 (19)
C15	0.083 (3)	0.065 (3)	0.078 (3)	0.008 (2)	−0.024 (2)	−0.0182 (19)

Geometric parameters (Å, º) top

O1W—H1A	0.840	C6—C7	1.378 (4)
O1W—H1B	0.840	C6—H6	0.93
O1—C1	1.402 (3)	C7—C8	1.385 (3)
O1—H1	0.82	C7—H7	0.93
O2—C2	1.415 (3)	C8—C9	1.378 (3)
O2—H2	0.82	C8—H8	0.93
O3—C3	1.200 (3)	C11—C12	1.489 (4)
O4—C10	1.297 (3)	C11—H11A	0.97
O4—H4	0.82	C11—H11B	0.97
O5—C10	1.208 (3)	C12—C13	1.306 (4)
C1—C9	1.514 (3)	C12—H12	0.93
C1—C10	1.527 (3)	C13—C15	1.490 (5)
C1—C2	1.564 (3)	C13—C14	1.501 (4)
C2—C3	1.528 (3)	C14—H14A	0.96
C2—C11	1.534 (3)	C14—H14B	0.96
C3—C4	1.471 (3)	C14—H14C	0.96
C4—C9	1.381 (3)	C15—H15A	0.96
C4—C5	1.386 (3)	C15—H15B	0.96
C5—C6	1.376 (4)	C15—H15C	0.96
C5—H5	0.93

H1A—O1W—H1B	118	C9—C8—H8	121
C1—O1—H1	109.5	C7—C8—H8	121
C2—O2—H2	109.5	C8—C9—C4	120.5 (2)
C10—O4—H4	109.5	C8—C9—C1	127.7 (2)
O1—C1—C9	109.97 (18)	C4—C9—C1	111.8 (2)
O1—C1—C10	109.13 (17)	O5—C10—O4	124.5 (2)
C9—C1—C10	109.80 (18)	O5—C10—C1	122.6 (2)
O1—C1—C2	116.27 (18)	O4—C10—C1	112.94 (19)
C9—C1—C2	102.25 (17)	C12—C11—C2	112.8 (2)
C10—C1—C2	109.17 (18)	C12—C11—H11A	109
O2—C2—C3	111.45 (19)	C2—C11—H11A	109
O2—C2—C11	108.25 (18)	C12—C11—H11B	109
C3—C2—C11	109.75 (19)	C2—C11—H11B	109
O2—C2—C1	114.67 (18)	H11A—C11—H11B	107.8
C3—C2—C1	103.27 (18)	C13—C12—C11	126.9 (3)
C11—C2—C1	109.33 (18)	C13—C12—H12	116.5
O3—C3—C4	128.8 (2)	C11—C12—H12	116.5
O3—C3—C2	124.4 (2)	C12—C13—C15	123.7 (3)
C4—C3—C2	106.77 (19)	C12—C13—C14	122.3 (3)
C9—C4—C5	121.5 (2)	C15—C13—C14	113.9 (3)
C9—C4—C3	109.08 (19)	C13—C14—H14A	109.5
C5—C4—C3	129.4 (2)	C13—C14—H14B	109.5
C6—C5—C4	117.7 (2)	H14A—C14—H14B	109.5
C6—C5—H5	121.2	C13—C14—H14C	109.5
C4—C5—H5	121.2	H14A—C14—H14C	109.5
C5—C6—C7	120.9 (2)	H14B—C14—H14C	109.5
C5—C6—H6	119.5	C13—C15—H15A	109.5
C7—C6—H6	119.5	C13—C15—H15B	109.5
C6—C7—C8	121.4 (3)	H15A—C15—H15B	109.5
C6—C7—H7	119.3	C13—C15—H15C	109.5
C8—C7—H7	119.3	H15A—C15—H15C	109.5
C9—C8—C7	118.0 (2)	H15B—C15—H15C	109.5

O1—C1—C2—O2	−94.2 (2)	C7—C8—C9—C4	0.1 (3)
C9—C1—C2—O2	146.03 (19)	C7—C8—C9—C1	178.9 (2)
C10—C1—C2—O2	29.8 (2)	C5—C4—C9—C8	1.0 (3)
O1—C1—C2—C3	144.38 (19)	C3—C4—C9—C8	−179.4 (2)
C9—C1—C2—C3	24.6 (2)	C5—C4—C9—C1	−177.9 (2)
C10—C1—C2—C3	−91.7 (2)	C3—C4—C9—C1	1.7 (3)
O1—C1—C2—C11	27.6 (3)	O1—C1—C9—C8	40.0 (3)
C9—C1—C2—C11	−92.2 (2)	C10—C1—C9—C8	−80.0 (3)
C10—C1—C2—C11	151.53 (18)	C2—C1—C9—C8	164.2 (2)
O2—C2—C3—O3	30.5 (3)	O1—C1—C9—C4	−141.13 (19)
C11—C2—C3—O3	−89.4 (3)	C10—C1—C9—C4	98.8 (2)
C1—C2—C3—O3	154.2 (2)	C2—C1—C9—C4	−17.0 (2)
O2—C2—C3—C4	−148.40 (18)	O1—C1—C10—O5	0.7 (3)
C11—C2—C3—C4	91.7 (2)	C9—C1—C10—O5	121.3 (2)
C1—C2—C3—C4	−24.8 (2)	C2—C1—C10—O5	−127.3 (2)
O3—C3—C4—C9	−163.8 (2)	O1—C1—C10—O4	−179.68 (19)
C2—C3—C4—C9	15.1 (2)	C9—C1—C10—O4	−59.1 (3)
O3—C3—C4—C5	15.8 (4)	C2—C1—C10—O4	52.3 (2)
C2—C3—C4—C5	−165.4 (2)	O2—C2—C11—C12	−69.4 (3)
C9—C4—C5—C6	−1.6 (4)	C3—C2—C11—C12	52.5 (3)
C3—C4—C5—C6	179.0 (2)	C1—C2—C11—C12	165.1 (2)
C4—C5—C6—C7	1.0 (4)	C2—C11—C12—C13	−123.5 (3)
C5—C6—C7—C8	0.1 (4)	C11—C12—C13—C15	0.3 (5)
C6—C7—C8—C9	−0.7 (4)	C11—C12—C13—C14	178.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.93	2.729 (2)	166
O2—H2···O1ⁱⁱ	0.82	2.08	2.846 (2)	155
O4—H4···O1Wⁱⁱ	0.82	1.72	2.520 (3)	164
O1W—H1B···O5ⁱⁱⁱ	0.84	1.96	2.785 (3)	167
O1W—H1A···O5	0.84	2.05	2.884 (3)	173

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆O₅·H₂O
M_r	294.29
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	9.5514 (7), 5.7762 (5), 13.1324 (9)
β (°)	92.126 (12)
V (Å³)	724.03 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.21 × 0.15 × 0.09

Data collection
Diffractometer	Enraf–Nonius FR590
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	18985, 1827, 1490
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.093, 1.06
No. of reflections	1827
No. of parameters	195
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: COLLECT (Nonius, 2004), DIRAX/LSQ (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae, 2006) and ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.93	2.729 (2)	166.3
O2—H2···O1ⁱⁱ	0.82	2.08	2.846 (2)	154.7
O4—H4···O1Wⁱⁱ	0.82	1.72	2.520 (3)	164.2
O1W—H1B···O5ⁱⁱⁱ	0.84	1.96	2.785 (3)	167
O1W—H1A···O5	0.84	2.05	2.884 (3)	173

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

Acknowledgements

This work was supported by the Brazilian agencies FAPEAL, FAPERJ, CAPES and CNPq.

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,2-Dihydr­­oxy-2-(3-methyl­but-2-en­yl)-3-oxo-2,3-di­hydro-1H-indene-1-carboxylic acid monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,2-Dihydroxy-2-(3-methylbut-2-enyl)-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid monohydrate