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Crystal structure of ethyl (6-hy­dr­oxy-1-benzo­furan-3-yl)acetate sesquihydrate

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, India, bInstitution of Excellence, Vijnana Bhavan, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: nirmaldb@rediffmail.com

Edited by M. Gdaniec, Adam Mickiewicz University, Poland (Received 16 October 2014; accepted 5 November 2014; online 21 November 2014)

In the title hydrate, C12H12O4·1.5H2O, one of the water mol­ecules in the asymmetric unit is located on a twofold rotation axis. The mol­ecule of the benzo­furan derivative is essentially planar (r.m.s. deviation for the non-H atoms = 0.021 Å), with the ester group adopting a fully extended conformation. In the crystal, O—H⋯O hydrogen bonds between the water mol­ecules and the hy­droxy groups generate a centrosymmetric R66(12) ring motif. These R66(12) rings are fused, forming a one-dimensional motif extending along the c-axis direction.

1. Chemical context

Furan heterocycles are of inter­est for synthetic chemists as they possess various pharmacological and biological activities including anti­tuberculosis (Tawari et al., 2010[Tawari, N. R., Bairwa, R., Ray, M. K., Rajan, M. G. R. & Degani, M. S. (2010). Bioorg. Med. Chem. Lett. 20, 6175-6178.]), anti-inflammatory (Shin et al., 2011[Shin, J.-S., Park, S.-J., Ryu, S., Kang, H. B., Kim, T. W., Choi, J.-H., Lee, J.-Y., Cho, Y.-W. & Lee, K.-T. (2011). Br. J. Pharm. 165, 1926-1940.]) and anti­bacterial (Kirilmis et al., 2008[Kirilmis, C., Ahmedzade, M., Servi, S., Koca, M., Kizirgil, A. & Kazaz, C. (2008). Eur. J. Med. Chem. 43, 300-308.]) activity. Substituted benzo­furans have found applications as fluorescent sensors (Oter et al., 2007[Oter, O., Ertekin, K., Kirilmis, C., Koca, M. & Ahmedzade, M. (2007). Sens. Actuators B Chem. 122, 450-456.]), anti-oxidants, brightening agents and drugs. Moreover, benzo­furan carb­oxy­lic acid ethyl ester also exhibits selective cytotoxicity against a tumorigenic cell line (Hayakawa et al., 2004[Hayakawa, I., Shioya, R., Agatsuma, T., Furukawa, H., Naruto, S. & Sugano, Y. (2004). Bioorg. Med. Chem. Lett. 14, 455-458.]). In view of the above facts, and as a continuation of our structural studies on benzo­furans (Arunakumar, Krishnaswamy et al., 2014[Arunakumar, D. B., Krishnaswamy, G., Sreenivasa, S., Pampa, K. J., Lokanath, N. K. & Suchetan, P. A. (2014). Acta Cryst. E70, o87.]; Arunakumar, Desai Nivedita et al., 2014[Arunakumar, D. B., Nivedita, R. D., Sreenivasa, S., Madan Kumar, S., Lokanath, N. K. & Suchetan, P. A. (2014). Acta Cryst. E70, o40.]), the title compound has been synthesized, characterized by FT IR, 1H NMR and LC–MS methods and its crystal structure determined.

[Scheme 1]

2. Structural commentary

The title compound crystallizes as a 1.5-hydrate with one of the symmetry-independent water mol­ecules occupying a special position of C2 symmetry. The mol­ecular structure of the title compound is shown in Fig. 1[link]. The mol­ecule is almost planar (r.m.s. deviation for the non-H atoms = 0.021 Å) and the ethyl acetate fragment adopts a fully extended conformation.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

3. Supra­molecular features

Hydrogen bonds (Table 1[link]) between two hy­droxy groups and four water mol­ecules generate a centrosymmetric [R_{6}^{6}](12) ring motif. The rings are fused at the position of the O5 atoms, i.e. through water mol­ecules located at special positions. In effect, two anti­parallel chains of hydrogen bonds are formed that are fused at every fourth O atom and which propagate along the crystallographic c-axis (Fig. 2[link]). In the crystal, the components are connected into a three-dimensional network through additional hydrogen bonds between the water mol­ecule in a general position and the ester carbonyl group. In addition to strong hydrogen bonds, weaker C—H⋯π inter­actions are observed between the methyl­ene group H atoms and the benzene and furan rings (Fig. 3[link] and Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7/C13/C9/C8/C11/C14 benzene ring and Cg2 is the centroid of the O16/C6/C10/C7/C13 furan ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2 0.82 1.88 2.692 (4) 170
O2—H2A⋯O3i 0.85 1.96 2.788 (4) 164
O2—H2B⋯O5ii 0.85 2.00 2.844 (4) 174
O5—H5⋯O1iii 0.85 (4) 2.09 (4) 2.870 (3) 152 (4)
C17—H17BCg1iv 0.97 2.68 3.485 (3) 140
C17—H17ACg2v 0.97 2.99 3.889 (3) 154
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+2, z+{\script{1\over 2}}]; (iii) [-x+1, y, -z+{\script{1\over 2}}]; (iv) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (v) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].
[Figure 2]
Figure 2
Hydrogen-bonding inter­actions (dashed lines) featuring a fused [R_{6}^{6}](12) ring motif.
[Figure 3]
Figure 3
The C—H⋯π inter­actions (dashed lines) in the title compound.

4. Synthesis and crystallization

2-(6-Hy­droxy-1-benzo­furan-3-yl)acetic acid (2.0 g, 0.010 mmol) was taken in a round-bottomed flask containing ethanol (10 mL). Concentrated sulfuric acid (1 mL) was added and the reaction mixture was refluxed for 4 h at 353 K. After completion of the reaction, the reaction mixture was poured into ice-cold water and extracted to an ethyl acetate layer. The organic layer was washed with water followed by brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated under vacuum, giving a reddish residue. The residue was purified by column chromatography using silica gel (60–120 mesh) and ethyl acetate/petroleum ether (2:8) as eluent, affording a colourless crystalline product. Crystals suitable for X-ray analysis were formed by slow evaporation of the solution of the compound in ethyl acetate and petroleum ether (3:2) at room temperature. As the product had been water worked-up, water might have entered in the solid interstices during work-up.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The H atoms of water mol­ecules were located from a difference Fourier map. The H atom bound to O5 was freely refined and those bound to O2 had the O—H distances restrained to 0.85 (2) Å. The remaining C/O-bound H atoms were fixed geometrically (C—H = 0.93–0.97 and O—H = 0.82 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C,O) for methyl and hy­droxy H atoms, and 1.2Ueq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula 2C12H12O4·3H2O
Mr 494.48
Crystal system, space group Monoclinic, C2/c
Temperature (K) 296
a, b, c (Å) 29.191 (6), 7.3291 (17), 12.587 (3)
β (°) 113.074 (13)
V3) 2477.4 (9)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.89
Crystal size (mm) 0.47 × 0.34 × 0.26
 
Data collection
Diffractometer Bruker APEXII
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.730, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections 8441, 1968, 1132
Rint 0.114
(sin θ/λ)max−1) 0.584
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.224, 1.06
No. of reflections 1968
No. of parameters 168
No. of restraints 1
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.40, −0.54
Computer programs: APEX2, SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Supporting information


Chemical context top

Furan heterocycles are inter­esting for synthetic chemists as they possess various pharmacological and biological activities including anti­tuberculosis (Tawari et al., 2010), anti-inflammatory (Shin et al., 2011) and anti­bacterial (Kirilmis et al., 2008). Substituted benzo­furans have found applications as fluorescent sensors (Oter et al., 2007), anti-oxidants, brightening agents and drugs. Moreover, benzo­furan carb­oxy­lic acid ethyl ester exhibits selective cytotoxicity against a tumorigenic cell line (Hayakawa et al., 2004). In view of the above facts, and as a continuation of our structural studies on benzo­furans (Arunakumar, Krishnaswamy et al., 2014; Arunakumar, Desai Nivedita et al., 2014), the title compound has been synthesized, characterized by FT IR, 1H NMR and LC–MS methods and its crystal structure determined.

Structural commentary top

The title compound crystallizes as a 1.5-hydrate with one of the symmetry-independent water molecules occupying a special position of C2 symmetry. The molecular structure of the title compound is shown in Fig. 1. The molecule is almost planar (r.m.s. deviation for the non-H atoms = 0.021 Å) and the ethyl acetate fragment adopts a fully extended conformation.

Supra­molecular features top

Hydrogen bonds (Table 1) between two hy­droxy groups and four water molecules generate a centrosymmetric R66(12) ring motif. The rings are fused at the position of the O5 atoms, i.e. through water molecules located at special positions. In effect, two anti­parallel chains of hydrogen bonds are formed that are fused at every fourth O atom and which propagate along the crystallographic c-axis (Fig. 2). The crystal components are connected into a three-dimensional network through additional hydrogen bonds between the water molecule in a general position and the ester carbonyl group. In addition to strong hydrogen bonds, weaker C—H···π inter­actions are observed between the methyl­ene group H atoms and the benzene and furan rings (Fig. 3 and Table 1).

Synthesis and crystallization top

2-(6-Hy­droxy-1-benzo­furan-3-yl)acetic acid (2.0 g, 0.010 mmol) was taken in a round-bottomed flask containing ethanol (10 ml). Concentrated sulfuric acid (1 ml) was added and the reaction mixture was refluxed for 4 h at 353 K. After completion of the reaction, the reaction mixture was poured into ice-cold water and extracted to an ethyl acetate layer. The organic layer was washed with water followed by brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated under vacuum, giving a reddish residue. The residue was purified by column chromatography using silica gel (60–120 mesh) and ethyl acetate/petroleum ether (2:8) as eluent, affording a colourless crystalline product. Crystals suitable for X-ray analysis were formed by slow evaporation of the solution of the compound in ethyl acetate and petroleum ether (3:2) at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms of water molecules were located from a difference Fourier map. The H atom bound to O5 was freely refined and those bound to O2 had the O—H distances restrained to 0.85 (2) Å. The remaining C/O-bound H atoms were fixed geometrically (C—H = 0.93–0.97 and O—H = 0.82 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C,O) for methyl and hy­droxy H atoms, and 1.2Ueq(C) for other H atoms.

Related literature top

For related literature, see: Hayakawa et al. (2004); Kirilmis et al. (2008); Oter et al. (2007); Shin et al. (2011); Tawari et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Hydrogen-bonding interactions (dashed lines) featuring a fused R66(12) ring motif.

The C—H···π interactions (dashed lines) in the title compound.
Ethyl (6-hydroxy-1-benzofuran-3-yl)acetate sesquihydrate top
Crystal data top
2C12H12O4·3H2Oprism
Mr = 494.48Dx = 1.326 Mg m3
Monoclinic, C2/cMelting point: 447 K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54178 Å
a = 29.191 (6) ÅCell parameters from 125 reflections
b = 7.3291 (17) Åθ = 6.3–64.2°
c = 12.587 (3) ŵ = 0.89 mm1
β = 113.074 (13)°T = 296 K
V = 2477.4 (9) Å3Prism, colourless
Z = 40.47 × 0.34 × 0.26 mm
F(000) = 1048
Data collection top
Bruker APEXII
diffractometer
1968 independent reflections
Radiation source: fine-focus sealed tube1132 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.114
phi and ϕ scansθmax = 64.2°, θmin = 6.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 3133
Tmin = 0.730, Tmax = 0.793k = 88
8441 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.224H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.1328P)2]
where P = (Fo2 + 2Fc2)/3
1968 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 0.40 e Å3
1 restraintΔρmin = 0.54 e Å3
Crystal data top
2C12H12O4·3H2OV = 2477.4 (9) Å3
Mr = 494.48Z = 4
Monoclinic, C2/cCu Kα radiation
a = 29.191 (6) ŵ = 0.89 mm1
b = 7.3291 (17) ÅT = 296 K
c = 12.587 (3) Å0.47 × 0.34 × 0.26 mm
β = 113.074 (13)°
Data collection top
Bruker APEXII
diffractometer
1968 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
1132 reflections with I > 2σ(I)
Tmin = 0.730, Tmax = 0.793Rint = 0.114
8441 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0671 restraint
wR(F2) = 0.224H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.40 e Å3
1968 reflectionsΔρmin = 0.54 e Å3
168 parameters
Special details top

Experimental. Thin-layer chromatography (TLC) was carried out on Merck pre-coated silica gel plates to monitor the progress of the reaction. The FT–IR spectra were recorded as KBr pellets using JASCO FT–IR-4100 spectrophotometer in the range 4000–400 cm-1 at a resolution of 2 cm-1. 1H NMR spectra were recorded in CDCl3 and DMSO-d6 on a JEOL-400 MHz NMR instrument. Chemical shifts are reported in δ values in parts per million relative to TMS. Mass spectral data were obtained on an Agilent LC–MS column C-18 instrument.

The IR spectrum of (I) exhibits strong bands at 1686 cm-1 and 1193 cm-1 due to C=O and C-O stretchings, respectively. A single band appearing at 3340 cm-1 is due to OH group stretching. Appearance of bands in the range 3011–2907 cm-1 is due to aromatic stretching and bands in the range 2970–2815 cm-1 are due to C—H stretching, thus confirming the presence of the saturated hydrocarbons in (I).

The 1H NMR spectrum of (I) shows peaks at δ 9.53 (s, 1H, Ar-OH), 6.69 (s, 1H, furan-H), 7.35–7.33 (d, 1H, Ar-H), 6.88–6.87 (d, 1H, Ar-H), 6.75–6.72 (q, 1H, Ar-H), 4.12–4.07 (q, 2H, OCH2), 3.34 (s, 2H, CH2), 1.12–1.17 (t, 3H, CH3). The LC–MS spectrum shows the appearance of molecular ion peaks at m/z 221 and 222 values, confirming the structure of the compound.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
xyzUiso*/Ueq
O160.74036 (8)0.9708 (4)0.7193 (2)0.0605 (10)
C70.71590 (10)0.9610 (4)0.5264 (3)0.0378 (10)
C80.61898 (11)0.8688 (4)0.4921 (3)0.0391 (11)
C90.65308 (11)0.8957 (4)0.6055 (3)0.0448 (11)
H90.64440.88460.66890.054*
C100.76857 (11)1.0071 (4)0.5752 (3)0.0389 (10)
C110.63322 (12)0.8851 (4)0.3998 (3)0.0458 (11)
H110.60970.86460.32550.055*
C120.92468 (12)1.1583 (5)0.5340 (3)0.0523 (12)
H12A0.94491.06160.58240.063*
H12B0.93071.26930.57930.063*
C130.70057 (11)0.9401 (4)0.6160 (3)0.0405 (11)
C140.68085 (12)0.9305 (4)0.4142 (3)0.0427 (11)
H140.68970.94090.35100.051*
C150.93746 (14)1.1861 (6)0.4312 (4)0.0680 (15)
H15A0.92891.07860.38390.102*
H15B0.97251.20920.45640.102*
H15C0.91911.28840.38730.102*
C170.79811 (11)1.0380 (4)0.5048 (3)0.0420 (11)
H17A0.78191.13340.44950.050*
H17B0.79670.92750.46120.050*
C180.85173 (12)1.0893 (4)0.5659 (3)0.0410 (11)
O10.57017 (8)0.8246 (4)0.4691 (2)0.0512 (9)
H10.56670.80830.53010.077*
O20.54997 (10)0.7984 (4)0.6597 (2)0.0639 (10)
H2A0.56870.73100.71440.096*
H2B0.53650.87900.68660.096*
O30.87331 (9)1.1106 (3)0.6691 (2)0.0586 (9)
O40.87249 (9)1.1095 (3)0.4913 (2)0.0523 (9)
O50.50000.9512 (5)0.25000.0598 (13)
C60.77984 (12)1.0112 (5)0.6912 (3)0.0526 (12)
H60.81141.03880.74580.063*
H50.4849 (19)0.879 (5)0.194 (3)0.104 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O160.0473 (13)0.0952 (19)0.0313 (16)0.0166 (11)0.0069 (14)0.0131 (13)
C70.0405 (15)0.0324 (14)0.036 (2)0.0010 (10)0.0098 (17)0.0003 (14)
C80.0393 (15)0.0418 (16)0.035 (2)0.0035 (10)0.0137 (17)0.0009 (15)
C90.0420 (16)0.0557 (18)0.034 (2)0.0000 (12)0.0121 (17)0.0065 (16)
C100.0428 (15)0.0362 (15)0.036 (2)0.0021 (10)0.0130 (17)0.0033 (15)
C110.0424 (16)0.0578 (19)0.028 (2)0.0010 (12)0.0038 (18)0.0009 (16)
C120.0406 (17)0.060 (2)0.054 (3)0.0104 (12)0.0155 (19)0.0029 (19)
C130.0419 (16)0.0455 (16)0.029 (2)0.0013 (12)0.0082 (17)0.0069 (15)
C140.0474 (16)0.0490 (17)0.029 (2)0.0053 (12)0.0125 (17)0.0032 (15)
C150.059 (2)0.088 (3)0.064 (3)0.0184 (18)0.032 (2)0.005 (2)
C170.0401 (15)0.0410 (16)0.038 (2)0.0023 (11)0.0077 (16)0.0006 (15)
C180.0442 (16)0.0346 (15)0.042 (2)0.0033 (11)0.0148 (19)0.0008 (15)
O10.0382 (11)0.0702 (15)0.0411 (15)0.0032 (9)0.0112 (12)0.0030 (14)
O20.0591 (15)0.0818 (19)0.0477 (17)0.0184 (11)0.0176 (14)0.0097 (15)
O30.0555 (14)0.0800 (17)0.0344 (16)0.0188 (11)0.0114 (14)0.0080 (13)
O40.0423 (12)0.0624 (14)0.0454 (16)0.0119 (9)0.0100 (13)0.0003 (12)
O50.0500 (18)0.065 (2)0.053 (3)0.0000.008 (2)0.000
C60.0398 (17)0.079 (2)0.040 (2)0.0127 (14)0.0166 (18)0.017 (2)
Geometric parameters (Å, º) top
O16—C61.364 (5)C12—H12A0.9700
O16—C131.381 (3)C12—H12B0.9700
C7—C131.375 (5)C14—H140.9300
C7—C141.399 (4)C15—H15A0.9600
C7—C101.454 (4)C15—H15B0.9600
C8—O11.377 (4)C15—H15C0.9600
C8—C111.385 (6)C17—C181.496 (4)
C8—C91.397 (4)C17—H17A0.9700
C9—C131.379 (5)C17—H17B0.9700
C9—H90.9300C18—O31.211 (4)
C10—C61.365 (6)C18—O41.309 (5)
C10—C171.476 (5)O1—H10.8200
C11—C141.371 (6)O2—H2A0.8499
C11—H110.9300O2—H2B0.8500
C12—O41.448 (4)O5—H50.854 (19)
C12—C151.494 (6)C6—H60.9300
C6—O16—C13106.0 (3)C11—C14—C7118.4 (4)
C13—C7—C14117.7 (3)C11—C14—H14120.8
C13—C7—C10108.0 (3)C7—C14—H14120.8
C14—C7—C10134.2 (4)C12—C15—H15A109.5
O1—C8—C11118.1 (3)C12—C15—H15B109.5
O1—C8—C9120.8 (4)H15A—C15—H15B109.5
C11—C8—C9121.1 (3)C12—C15—H15C109.5
C13—C9—C8114.7 (4)H15A—C15—H15C109.5
C13—C9—H9122.6H15B—C15—H15C109.5
C8—C9—H9122.6C10—C17—C18118.0 (3)
C6—C10—C7103.2 (4)C10—C17—H17A107.8
C6—C10—C17133.3 (3)C18—C17—H17A107.8
C7—C10—C17123.5 (3)C10—C17—H17B107.8
C14—C11—C8122.2 (3)C18—C17—H17B107.8
C14—C11—H11118.9H17A—C17—H17B107.1
C8—C11—H11118.9O3—C18—O4124.2 (3)
O4—C12—C15107.3 (3)O3—C18—C17125.6 (4)
O4—C12—H12A110.3O4—C18—C17110.2 (3)
C15—C12—H12A110.3C8—O1—H1109.5
O4—C12—H12B110.3H2A—O2—H2B109.5
C15—C12—H12B110.3C18—O4—C12118.5 (3)
H12A—C12—H12B108.5O16—C6—C10113.5 (3)
C7—C13—C9125.9 (3)O16—C6—H6123.3
C7—C13—O16109.3 (3)C10—C6—H6123.3
C9—C13—O16124.9 (4)
O1—C8—C9—C13179.7 (3)C6—O16—C13—C9179.7 (3)
C11—C8—C9—C130.5 (4)C8—C11—C14—C70.0 (4)
C13—C7—C10—C60.6 (3)C13—C7—C14—C111.2 (4)
C14—C7—C10—C6178.3 (3)C10—C7—C14—C11178.8 (3)
C13—C7—C10—C17179.3 (3)C6—C10—C17—C181.7 (5)
C14—C7—C10—C171.6 (5)C7—C10—C17—C18178.5 (3)
O1—C8—C11—C14179.3 (3)C10—C17—C18—O31.1 (5)
C9—C8—C11—C140.9 (5)C10—C17—C18—O4179.3 (2)
C14—C7—C13—C91.7 (5)O3—C18—O4—C120.7 (5)
C10—C7—C13—C9179.9 (3)C17—C18—O4—C12179.6 (2)
C14—C7—C13—O16178.4 (2)C15—C12—O4—C18175.7 (3)
C10—C7—C13—O160.2 (3)C13—O16—C6—C100.6 (4)
C8—C9—C13—C70.8 (4)C7—C10—C6—O160.7 (4)
C8—C9—C13—O16179.3 (3)C17—C10—C6—O16179.2 (3)
C6—O16—C13—C70.2 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C7/C13/C9/C8/C11/C14 benzene ring and Cg2 is the centroid of the O16/C6/C10/C7/C13 furan ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.882.692 (4)170
O2—H2A···O3i0.851.962.788 (4)164
O2—H2B···O5ii0.852.002.844 (4)174
O5—H5···O1iii0.85 (4)2.09 (4)2.870 (3)152 (4)
C17—H17B···Cg1iv0.972.683.485 (3)140
C17—H17A···Cg2v0.972.993.889 (3)154
Symmetry codes: (i) x+3/2, y1/2, z+3/2; (ii) x, y+2, z+1/2; (iii) x+1, y, z+1/2; (iv) x+1/2, y+3/2, z; (v) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C7/C13/C9/C8/C11/C14 benzene ring and Cg2 is the centroid of the O16/C6/C10/C7/C13 furan ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.882.692 (4)170
O2—H2A···O3i0.851.962.788 (4)164
O2—H2B···O5ii0.852.002.844 (4)174
O5—H5···O1iii0.85 (4)2.09 (4)2.870 (3)152 (4)
C17—H17B···Cg1iv0.972.683.485 (3)140
C17—H17A···Cg2v0.972.993.889 (3)154
Symmetry codes: (i) x+3/2, y1/2, z+3/2; (ii) x, y+2, z+1/2; (iii) x+1, y, z+1/2; (iv) x+1/2, y+3/2, z; (v) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula2C12H12O4·3H2O
Mr494.48
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)29.191 (6), 7.3291 (17), 12.587 (3)
β (°) 113.074 (13)
V3)2477.4 (9)
Z4
Radiation typeCu Kα
µ (mm1)0.89
Crystal size (mm)0.47 × 0.34 × 0.26
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.730, 0.793
No. of measured, independent and
observed [I > 2σ(I)] reflections
8441, 1968, 1132
Rint0.114
(sin θ/λ)max1)0.584
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.224, 1.06
No. of reflections1968
No. of parameters168
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.54

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

 

Acknowledgements

The authors are thankful to the Department of Science and Technology, New Delhi, Government of India, for providing financial assistance under its DST FAST TRACK scheme [SR/FT/CS-81/2010 (G)]. The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction facility.

References

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