Redetermination of ethyl (3a-cis)-3a,8b-dihydr­oxy-2-methyl-4-oxo-3a,8b-dihydro-4H-indeno[1,2-b]furan-3-carboxyl­ate monohydrate

Pereira Silva, P.S.; Ghalib, R.M.; Mehdi, S.H.; Hashim, R.; Sulaiman, O.

doi:10.1107/S1600536809039403

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2616

https://doi.org/10.1107/S1600536809039403

Open

access

Redetermination of ethyl (3a-cis)-3a,8b-dihydroxy-2-methyl-4-oxo-3a,8b-dihydro-4H-indeno[1,2-b]furan-3-carboxylate monohydrate

P. S. Pereira Silva,^a Raza Murad Ghalib,^b Sayed Hasan Mehdi,^b Rokiah Hashim ^b and Othman Sulaiman ^b ^*

^aCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^bSchool of Industrial Technology, Universiti Sains Malaysia, 11800 Pulau Pinang, Malaysia
^*Correspondence e-mail: psidonio@pollux.fis.uc.pt

(Received 25 September 2009; accepted 28 September 2009; online 3 October 2009)

The crystal structure of the title compound, C₁₅H₁₄O₆·H₂O, has been redetermined from single-crystal X-ray data. The structure was originally determined by Peet et al. [J. Heterocycl. Chem. (1995), 32, 33–41] but the atomic coordinates were not reported or deposited in the Cambridge Structural Database. The ethyl substituent is disordered over two sites with refined occupancies of 0.815 (6) and 0.185 (6). The indeno group is almost planar [maximum deviation 0.0922 (14) Å] and makes an angle of 68.81 (4)° with the furan ring. The fused ring molecules are assembled in pairs by intermolecular O—H⋯O hydrogen bonds. The resulting dimers are also hydrogen bonded to the water molecules, forming double-stranded chains running along the a axis.

Related literature

For the previous report of the crystal structure, see: Peet et al. (1995 ). For chemical background, see: Black et al. (1994 ); Ruhemann (1910 ); Kaiser et al. (1970 ).

Experimental

Crystal data

C₁₅H₁₄O₆·H₂O
M_r = 308.28
Monoclinic, P 2₁ /c
a = 7.9740 (4) Å
b = 16.7524 (8) Å
c = 11.0041 (5) Å
β = 98.833 (2)°
V = 1452.53 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.49 × 0.46 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.894, T_max = 0.975
21608 measured reflections
3509 independent reflections
2820 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.154
S = 1.03
3509 reflections
215 parameters
27 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O14—H14⋯O21ⁱ	0.82	1.90	2.7103 (17)	172
O21—H21⋯O22	0.82	1.94	2.724 (2)	159
O22—H22A⋯O14ⁱⁱ	0.83 (3)	2.45 (3)	3.124 (2)	140 (3)
O22—H22B⋯O17ⁱⁱⁱ	0.89 (3)	2.11 (3)	2.972 (3)	163 (3)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x-1, y, z; (iii) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; 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/S1600536809039403/bt5075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039403/bt5075Isup2.hkl

checkCIF report

Comment top

Ninhydrin (2,2-Dihydroxyindane-1,3-dione) is a chemical used to detect α-amino acids, proteins and dipeptides. When it reacts with these free amines, a deep blue or purple color known as Ruhemann's purple is evolved (Ruhemann, 1910; Kaiser et al., 1970). It is one of the most widely used reagent for chemical development of fingerprints on porous surfaces. Ninhydrin in benzene undergoes electrophilic substitution at C2 of 3,5-dimethoxyaniline leading to the formation of indeno[1,2-b]indole. The corresponding reaction in water undergoes electrophilic substitution at C4 (Black et al., 1994).

The ethyl substituent of the tile compound is disordered over two sites with refined occupancies of 0.815 (6) and 0.185 (6). The indeno moiety is almost planar, with atoms C11 and C12 deviating by -0.0574 (13) and 0.0922 (14) Å, respectively, from the indeno plane. The angle between the indeno group and the furan ring is 68.81 (4) °.

Related literature top

For the previous report of the crystal structure, see: Peet et al. (1995). For chemical background, see: Black et al. (1994); Ruhemann (1910); Kaiser et al. (1970).

Experimental top

A mixture of ninhydrin (1.78 g) and ethyl acetoacetate (1.27 ml) in molar ratio 1:1 were refluxed in acetone for thirty minutes in presence of Mg/HCl. The reaction mixture was filtered and dried at low pressure. The dried mass was crystallized with solvent system diethyl ether and hexane to give transparent crystals (mp 373–376 K) of title compound (2.68 g).

The melting point was determined on a Kofler block melting point apparatus and is uncorrected.

Structure description top

For the previous report of the crystal structure, see: Peet et al. (1995). For chemical background, see: Black et al. (1994); Ruhemann (1910); Kaiser et al. (1970).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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. ORTEPII (Spek, 2009) plot of the title compound. Displacement ellipsoids are drawn at the 50% probability level. For clarity only the ethyl group with the highest occupancy is shown.
	Fig. 2. Packing diagram, viewed down the a axis, with the hydrogen bonds depicted as dashed lines.

ethyl (3a-cis)-3a,8b-dihydroxy-2-methyl- 4-oxo-3a,8b-dihydro-4H-indeno[1,2-b]furan-3-carboxylate monohydrate top

Crystal data top

C₁₅H₁₄O₆·H₂O	F(000) = 648
M_r = 308.28	D_x = 1.410 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 373–376 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.9740 (4) Å	Cell parameters from 5159 reflections
b = 16.7524 (8) Å	θ = 2.2–27.9°
c = 11.0041 (5) Å	µ = 0.11 mm⁻¹
β = 98.833 (2)°	T = 293 K
V = 1452.53 (12) Å³	Parallelepipedic, colourless
Z = 4	0.49 × 0.46 × 0.22 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3509 independent reflections
Radiation source: fine-focus sealed tube	2820 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 28.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
T_min = 0.894, T_max = 0.975	k = −22→22
21608 measured reflections	l = −9→14

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0682P)² + 0.9584P] where P = (F_o² + 2F_c²)/3
3509 reflections	(Δ/σ)_max < 0.001
215 parameters	Δρ_max = 0.50 e Å⁻³
27 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₅H₁₄O₆·H₂O	V = 1452.53 (12) Å³
M_r = 308.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9740 (4) Å	µ = 0.11 mm⁻¹
b = 16.7524 (8) Å	T = 293 K
c = 11.0041 (5) Å	0.49 × 0.46 × 0.22 mm
β = 98.833 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3509 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2820 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.975	R_int = 0.019
21608 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	27 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.50 e Å⁻³
3509 reflections	Δρ_min = −0.38 e Å⁻³
215 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	Occ. (<1)
O8	0.60398 (14)	0.49466 (7)	0.73529 (11)	0.0366 (3)
O13	0.19037 (18)	0.31575 (9)	0.78551 (16)	0.0590 (4)
O14	0.69530 (14)	0.43316 (7)	0.92132 (11)	0.0353 (3)
H14	0.6687	0.4710	0.9617	0.053*
O17	0.04534 (18)	0.49231 (10)	0.79040 (16)	0.0641 (5)
O18	0.10479 (19)	0.57149 (12)	0.64190 (19)	0.0820 (6)
O21	0.36289 (15)	0.43437 (7)	0.95007 (10)	0.0354 (3)
H21	0.2683	0.4176	0.9572	0.053*
C1	0.4633 (2)	0.30757 (10)	0.71894 (16)	0.0368 (4)
C2	0.4601 (3)	0.23627 (12)	0.65306 (19)	0.0488 (5)
H2	0.3606	0.2069	0.6338	0.059*
C3	0.6090 (3)	0.21116 (13)	0.6179 (2)	0.0568 (5)
H3	0.6102	0.1642	0.5729	0.068*
C4	0.7575 (3)	0.25430 (13)	0.6479 (2)	0.0552 (5)
H4	0.8572	0.2349	0.6247	0.066*
C5	0.7612 (2)	0.32559 (12)	0.71189 (18)	0.0443 (4)
H5	0.8609	0.3549	0.7308	0.053*
C6	0.6107 (2)	0.35153 (10)	0.74655 (15)	0.0331 (3)
C7	0.58235 (19)	0.42670 (9)	0.81511 (15)	0.0298 (3)
C9	0.4506 (2)	0.52675 (10)	0.69420 (16)	0.0353 (4)
C10	0.3220 (2)	0.49272 (10)	0.74201 (15)	0.0349 (4)
C11	0.38915 (19)	0.42608 (9)	0.82712 (14)	0.0295 (3)
C12	0.3265 (2)	0.34408 (10)	0.77556 (16)	0.0364 (4)
C15	0.4550 (3)	0.59275 (13)	0.6050 (2)	0.0521 (5)
H15A	0.4636	0.5710	0.5255	0.078*
H15B	0.5514	0.6262	0.6316	0.078*
H15C	0.3530	0.6237	0.6003	0.078*
C16	0.1456 (2)	0.51738 (12)	0.72845 (19)	0.0473 (5)
C19A	−0.0681 (3)	0.6050 (2)	0.6333 (4)	0.0752 (11)	0.815 (6)
H19A	−0.1528	0.5633	0.6168	0.090*	0.815 (6)
H19B	−0.0826	0.6318	0.7092	0.090*	0.815 (6)
C20A	−0.0827 (4)	0.6619 (2)	0.5313 (4)	0.0808 (11)	0.815 (6)
H20A	−0.1885	0.6900	0.5258	0.121*	0.815 (6)
H20B	−0.0787	0.6336	0.4559	0.121*	0.815 (6)
H22C	0.0094	0.6993	0.5452	0.121*	0.815 (6)
C19B	−0.0660 (10)	0.5823 (6)	0.5692 (13)	0.0752 (11)	0.185 (6)
H19C	−0.0656	0.5693	0.4833	0.090*	0.185 (6)
H19D	−0.1491	0.5491	0.6008	0.090*	0.185 (6)
C20B	−0.1022 (16)	0.6673 (7)	0.5842 (16)	0.0808 (11)	0.185 (6)
H20D	−0.2188	0.6779	0.5520	0.121*	0.185 (6)
H20E	−0.0302	0.6988	0.5406	0.121*	0.185 (6)
H20F	−0.0811	0.6809	0.6700	0.121*	0.185 (6)
O22	0.0700 (2)	0.39329 (12)	1.03321 (17)	0.0620 (4)
H22A	−0.014 (4)	0.385 (2)	0.981 (3)	0.093*
H22B	0.057 (4)	0.4267 (19)	1.094 (3)	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O8	0.0297 (6)	0.0356 (6)	0.0467 (7)	0.0007 (5)	0.0130 (5)	0.0072 (5)
O13	0.0427 (7)	0.0543 (8)	0.0839 (11)	−0.0176 (6)	0.0219 (7)	−0.0161 (8)
O14	0.0289 (5)	0.0400 (6)	0.0368 (6)	0.0009 (5)	0.0037 (5)	−0.0057 (5)
O17	0.0353 (7)	0.0791 (11)	0.0817 (11)	0.0117 (7)	0.0211 (7)	0.0296 (9)
O18	0.0373 (8)	0.1084 (14)	0.1015 (14)	0.0201 (8)	0.0146 (8)	0.0643 (11)
O21	0.0326 (6)	0.0419 (6)	0.0340 (6)	−0.0026 (5)	0.0124 (5)	−0.0021 (5)
C1	0.0393 (9)	0.0326 (8)	0.0386 (8)	0.0005 (7)	0.0060 (7)	−0.0035 (7)
C2	0.0557 (11)	0.0380 (9)	0.0515 (11)	−0.0015 (8)	0.0048 (9)	−0.0099 (8)
C3	0.0738 (14)	0.0420 (10)	0.0554 (12)	0.0103 (10)	0.0124 (10)	−0.0158 (9)
C4	0.0573 (12)	0.0542 (12)	0.0580 (12)	0.0178 (10)	0.0211 (10)	−0.0093 (10)
C5	0.0384 (9)	0.0474 (10)	0.0491 (10)	0.0074 (8)	0.0131 (8)	−0.0057 (8)
C6	0.0335 (8)	0.0329 (8)	0.0334 (8)	0.0041 (6)	0.0063 (6)	−0.0015 (6)
C7	0.0267 (7)	0.0301 (7)	0.0336 (7)	0.0002 (6)	0.0078 (6)	0.0002 (6)
C9	0.0356 (8)	0.0340 (8)	0.0374 (8)	0.0035 (6)	0.0096 (6)	0.0020 (6)
C10	0.0308 (8)	0.0367 (8)	0.0377 (8)	0.0023 (6)	0.0070 (6)	0.0026 (7)
C11	0.0253 (7)	0.0312 (7)	0.0330 (7)	−0.0005 (6)	0.0075 (6)	−0.0011 (6)
C12	0.0323 (8)	0.0347 (8)	0.0423 (9)	−0.0032 (6)	0.0067 (7)	−0.0027 (7)
C15	0.0534 (11)	0.0497 (11)	0.0564 (12)	0.0053 (9)	0.0182 (9)	0.0179 (9)
C16	0.0333 (9)	0.0512 (11)	0.0577 (11)	0.0062 (8)	0.0080 (8)	0.0149 (9)
C19A	0.0372 (12)	0.114 (3)	0.076 (2)	0.0281 (14)	0.0150 (14)	0.043 (2)
C20A	0.0680 (18)	0.102 (2)	0.075 (3)	0.0325 (17)	0.0190 (17)	0.028 (2)
C19B	0.0372 (12)	0.114 (3)	0.076 (2)	0.0281 (14)	0.0150 (14)	0.043 (2)
C20B	0.0680 (18)	0.102 (2)	0.075 (3)	0.0325 (17)	0.0190 (17)	0.028 (2)
O22	0.0539 (9)	0.0752 (11)	0.0602 (10)	−0.0025 (8)	0.0193 (7)	0.0090 (8)

Geometric parameters (Å, º) top

O8—C9	1.349 (2)	C7—C11	1.566 (2)
O8—C7	1.4643 (19)	C9—C10	1.349 (2)
O13—C12	1.205 (2)	C9—C15	1.482 (3)
O14—C7	1.3658 (19)	C10—C16	1.452 (2)
O14—H14	0.8200	C10—C11	1.502 (2)
O17—C16	1.203 (2)	C11—C12	1.540 (2)
O18—C16	1.319 (2)	C15—H15A	0.9600
O18—C19A	1.478 (3)	C15—H15B	0.9600
O18—C19B	1.481 (5)	C15—H15C	0.9600
O21—C11	1.4073 (19)	C19A—C20A	1.463 (4)
O21—H21	0.8200	C19A—H19A	0.9700
C1—C6	1.380 (2)	C19A—H19B	0.9700
C1—C2	1.395 (2)	C20A—H20A	0.9600
C1—C12	1.470 (2)	C20A—H20B	0.9600
C2—C3	1.370 (3)	C20A—H22C	0.9600
C2—H2	0.9300	C19B—C20B	1.468 (6)
C3—C4	1.384 (3)	C19B—H19C	0.9700
C3—H3	0.9300	C19B—H19D	0.9700
C4—C5	1.384 (3)	C20B—H20D	0.9600
C4—H4	0.9300	C20B—H20E	0.9600
C5—C6	1.384 (2)	C20B—H20F	0.9600
C5—H5	0.9300	O22—H22A	0.83 (3)
C6—C7	1.503 (2)	O22—H22B	0.89 (3)

C9—O8—C7	109.07 (12)	C10—C11—C7	101.73 (12)
C7—O14—H14	109.5	C12—C11—C7	104.03 (12)
C16—O18—C19A	115.58 (18)	O13—C12—C1	127.76 (16)
C16—O18—C19B	125.4 (6)	O13—C12—C11	124.31 (16)
C19A—O18—C19B	31.6 (5)	C1—C12—C11	107.89 (13)
C11—O21—H21	109.5	C9—C15—H15A	109.5
C6—C1—C2	121.21 (17)	C9—C15—H15B	109.5
C6—C1—C12	110.30 (15)	H15A—C15—H15B	109.5
C2—C1—C12	128.35 (17)	C9—C15—H15C	109.5
C3—C2—C1	117.51 (19)	H15A—C15—H15C	109.5
C3—C2—H2	121.2	H15B—C15—H15C	109.5
C1—C2—H2	121.2	O17—C16—O18	122.50 (18)
C2—C3—C4	121.28 (18)	O17—C16—C10	124.07 (18)
C2—C3—H3	119.4	O18—C16—C10	113.43 (16)
C4—C3—H3	119.4	C20A—C19A—O18	105.1 (2)
C3—C4—C5	121.52 (19)	C20A—C19A—H19A	110.7
C3—C4—H4	119.2	O18—C19A—H19A	110.7
C5—C4—H4	119.2	C20A—C19A—H19B	110.7
C6—C5—C4	117.34 (18)	O18—C19A—H19B	110.7
C6—C5—H5	121.3	H19A—C19A—H19B	108.8
C4—C5—H5	121.3	C19A—C20A—H20A	109.5
C1—C6—C5	121.12 (16)	C19A—C20A—H20B	109.5
C1—C6—C7	111.65 (14)	H20A—C20A—H20B	109.5
C5—C6—C7	127.23 (16)	C19A—C20A—H22C	109.5
O14—C7—O8	109.19 (12)	H20A—C20A—H22C	109.5
O14—C7—C6	111.45 (13)	H20B—C20A—H22C	109.5
O8—C7—C6	108.04 (13)	C20B—C19B—O18	103.8 (5)
O14—C7—C11	117.14 (13)	C20B—C19B—H19C	111.0
O8—C7—C11	105.29 (12)	O18—C19B—H19C	111.0
C6—C7—C11	105.22 (12)	C20B—C19B—H19D	111.0
O8—C9—C10	113.90 (15)	O18—C19B—H19D	111.0
O8—C9—C15	113.99 (15)	H19C—C19B—H19D	109.0
C10—C9—C15	132.10 (17)	C19B—C20B—H20D	109.5
C9—C10—C16	128.49 (16)	C19B—C20B—H20E	109.5
C9—C10—C11	109.76 (14)	H20D—C20B—H20E	109.5
C16—C10—C11	121.49 (15)	C19B—C20B—H20F	109.5
O21—C11—C10	115.77 (13)	H20D—C20B—H20F	109.5
O21—C11—C12	110.76 (13)	H20E—C20B—H20F	109.5
C10—C11—C12	111.65 (13)	H22A—O22—H22B	117 (3)
O21—C11—C7	111.96 (12)

C6—C1—C2—C3	0.6 (3)	O14—C7—C11—O21	1.34 (19)
C12—C1—C2—C3	−174.61 (19)	O8—C7—C11—O21	−120.20 (13)
C1—C2—C3—C4	0.9 (3)	C6—C7—C11—O21	125.78 (13)
C2—C3—C4—C5	−1.7 (4)	O14—C7—C11—C10	125.58 (14)
C3—C4—C5—C6	1.1 (3)	O8—C7—C11—C10	4.03 (15)
C2—C1—C6—C5	−1.3 (3)	C6—C7—C11—C10	−109.99 (14)
C12—C1—C6—C5	174.74 (16)	O14—C7—C11—C12	−118.30 (14)
C2—C1—C6—C7	178.60 (16)	O8—C7—C11—C12	120.15 (13)
C12—C1—C6—C7	−5.4 (2)	C6—C7—C11—C12	6.13 (16)
C4—C5—C6—C1	0.4 (3)	C6—C1—C12—O13	−168.21 (19)
C4—C5—C6—C7	−179.43 (17)	C2—C1—C12—O13	7.4 (3)
C9—O8—C7—O14	−131.60 (14)	C6—C1—C12—C11	9.40 (19)
C9—O8—C7—C6	107.02 (14)	C2—C1—C12—C11	−174.95 (18)
C9—O8—C7—C11	−5.02 (16)	O21—C11—C12—O13	47.9 (2)
C1—C6—C7—O14	127.18 (15)	C10—C11—C12—O13	−82.7 (2)
C5—C6—C7—O14	−52.9 (2)	C7—C11—C12—O13	168.40 (18)
C1—C6—C7—O8	−112.85 (15)	O21—C11—C12—C1	−129.76 (14)
C5—C6—C7—O8	67.0 (2)	C10—C11—C12—C1	99.64 (15)
C1—C6—C7—C11	−0.76 (18)	C7—C11—C12—C1	−9.31 (17)
C5—C6—C7—C11	179.11 (17)	C19A—O18—C16—O17	5.4 (4)
C7—O8—C9—C10	4.1 (2)	C19B—O18—C16—O17	−29.6 (7)
C7—O8—C9—C15	−175.85 (15)	C19A—O18—C16—C10	−173.7 (3)
O8—C9—C10—C16	172.92 (18)	C19B—O18—C16—C10	151.3 (7)
C15—C9—C10—C16	−7.1 (3)	C9—C10—C16—O17	−166.7 (2)
O8—C9—C10—C11	−1.3 (2)	C11—C10—C16—O17	6.9 (3)
C15—C9—C10—C11	178.71 (19)	C9—C10—C16—O18	12.3 (3)
C9—C10—C11—O21	119.75 (16)	C11—C10—C16—O18	−174.08 (18)
C16—C10—C11—O21	−54.9 (2)	C16—O18—C19A—C20A	−179.3 (3)
C9—C10—C11—C12	−112.29 (16)	C19B—O18—C19A—C20A	−62.8 (10)
C16—C10—C11—C12	73.0 (2)	C16—O18—C19B—C20B	127.2 (10)
C9—C10—C11—C7	−1.87 (18)	C19A—O18—C19B—C20B	45.5 (9)
C16—C10—C11—C7	−176.54 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.82	1.90	2.7103 (17)	172
O21—H21···O22	0.82	1.94	2.724 (2)	159
O22—H22A···O14ⁱⁱ	0.83 (3)	2.45 (3)	3.124 (2)	140 (3)
O22—H22B···O17ⁱⁱⁱ	0.89 (3)	2.11 (3)	2.972 (3)	163 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₆·H₂O
M_r	308.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.9740 (4), 16.7524 (8), 11.0041 (5)
β (°)	98.833 (2)
V (Å³)	1452.53 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.49 × 0.46 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.894, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	21608, 3509, 2820
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.154, 1.03
No. of reflections	3509
No. of parameters	215
No. of restraints	27
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.38

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), 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
O14—H14···O21ⁱ	0.82	1.90	2.7103 (17)	171.5
O21—H21···O22	0.82	1.94	2.724 (2)	159.2
O22—H22A···O14ⁱⁱ	0.83 (3)	2.45 (3)	3.124 (2)	140 (3)
O22—H22B···O17ⁱⁱⁱ	0.89 (3)	2.11 (3)	2.972 (3)	163 (3)

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

Acknowledgements

The study was funded through USM short term grant No. 1001/PTEKIND/8140152. The authors acknowledge the USM for providing research facilities.

References

Black, D. C., Bowyer, M. C., Condie, G. C., Craig, D. C. & Kumar, N. (1994). Tetrahedron, 50, 10983–10994. CSD CrossRef CAS Web of Science Google Scholar
Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kaiser, E. R., Colescott, L., Bossinger, C. D. & Cook, P. I. (1970). Anal. Biochem. 34, 595–598. CrossRef CAS PubMed Web of Science Google Scholar
Peet, N. P., Huber, E. W. & Huffman, J. C. (1995). J. Heterocycl. Chem. 32, 33–41. CrossRef CAS Google Scholar
Ruhemann, S. (1910). J. Chem. Soc. 97, 2025–2031. CrossRef Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2616

https://doi.org/10.1107/S1600536809039403

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Redetermination of ethyl (3a-cis)-3a,8b-dihydr­­oxy-2-methyl-4-oxo-3a,8b-di­hydro-4H-indeno[1,2-b]furan-3-carboxyl­ate monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Redetermination of ethyl (3a-cis)-3a,8b-dihydroxy-2-methyl-4-oxo-3a,8b-dihydro-4H-indeno[1,2-b]furan-3-carboxylate monohydrate