Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3212
https://doi.org/10.1107/S1600536811046034

3-(4-Hy­dr­oxy­phen­yl)-7-meth­­oxy­chroman-4-one monohydrate

Zhu-Ping Xiao,a* Zhu-Yun Peng,a Qun Luo,a Ying Wua and Ye-Ling Yanga

aThe Key Laboratory of Ecotourism Application Technology of Hunan Province and College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
*Correspondence e-mail: xiaozhuping2005@163.com

(Received 27 October 2011; accepted 1 November 2011; online 5 November 2011)

In the title compound, C16H14O4·H2O, the dihedral angle betwen the benzene rings is 71.4 (6)°. The pyran ring is in a sofa conformation. In the crystal, O—H⋯O hydrogen bonds connect the components into a two-dimensional network parallel to (010), incorporating C22(4) and C22(11) chains. In addition, weak C—H⋯O, C—H⋯π and π–π stacking inter­actions [centroid–centroid distance = 3.768 (2) Å] are present.

Related literature

For background to and the biological activity of flavonoids, see: Xiao et al. (2007[Xiao, Z.-P., Xue, J.-Y., Tan, S.-H., Li, H.-Q. & Zhu, H.-L. (2007). Bioorg. Med. Chem. 15, 4212-4219.], 2010[Xiao, Z.-P., Ma, T.-W., Fu, W.-C., Peng, X.-C., Zhang, A.-H. & Zhu, H.-L. (2010). Eur. J. Med. Chem. 45, 5064-5070.], 2011[Xiao, Z.-P., Peng, Z.-Y., Peng, M.-J., Yan, W.-B., Ouyang, Y.-Z. & Zhu, H.-L. (2011). Mini-rev. Med. Chem. 11, 169-177.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C16H14O4·H2O

  • Mr = 288.29

  • Monoclinic, P 21 /c

  • a = 9.730 (3) Å

  • b = 17.977 (5) Å

  • c = 8.570 (2) Å

  • β = 106.194 (2)°

  • V = 1439.6 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.971, Tmax = 0.981

  • 11487 measured reflections

  • 3113 independent reflections

  • 2019 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.138

  • S = 1.04

  • 3113 reflections

  • 200 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C4–C9 and C10–C15 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O4—H4⋯O5 0.82 1.78 2.585 (2) 167
O5—H5A⋯O2i 0.91 (3) 1.86 (3) 2.742 (3) 163 (3)
O5—H5B⋯O4ii 0.97 (5) 1.78 (5) 2.734 (3) 168 (4)
C8—H8⋯O5iii 0.93 2.55 3.397 (3) 152
C2—H2⋯Cg1iv 0.98 2.86 3.745 (3) 151
C6—H6⋯Cg2v 0.93 2.97 3.748 (3) 142
Symmetry codes: (i) x+1, y, z; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x, y+{\script{5\over 2}}, -z+{\script{1\over 2}}]; (v) x-1, y, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046034/lh5364sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046034/lh5364Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046034/lh5364Isup3.cml

checkCIF report


Comment top

Flavonoids are a large group of phenolic plant constituents. Approximately 9000 different flavonoids from different plant sources have been described so far, and each year, hundreds of newly identified flavonoids are being recorded in the literature (Xiao, et al., 2011). Extensive epidemiological studies and in vitro experiments with polyphenols have indicate their broad variety of biological activities, including anticancer, anti-inflammatory, antibacterial, cardioprotective and enzyme-inhibitory activities (Xiao, et al., 2007,2010).

The title compound crystallizes as a hydrate (Fig. 1). The C4-C9 ring forms a dihedral angle of 71.4 (6) ° with the C10-C15 ring. In the pyran ring, atoms C2-C4/C9/O1 are essentially planar with a mean deviation of 0.0115 Å and C1 is 0.535 (2) Å from the plane of these atoms.

In the crystal, O—H···O hydrogen bonds connect the components into a two-dimensional network parallel to (010) incorparating C22(4) and C22(11) chains. In addtion, weak C—H···O, C—H···π(ring) interactions and π–π stacking interactions with a centroid to centroid distance of 3.768 (2) Å are present.

Related literature top

For background to and the biological activity of flavonoids, see: Xiao et al. (2007, 2010, 2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one (268 mg, 1 mmol) was dissolved in ethanol (10 ml). After 15 mg of 10% Pd/C was added under H2 atmosphere, the resulting mixture was stirred at room temperature for 6 h. After the catalyst was filtered off, the solvent was removed under reduced pressure. The residue was dissolved in ethanol (5 ml) and equal volume of water was then added. The crystals suitable for single crystal structure determination grown at room temperature by slow evaporation of a solution of the title compound in an ethanol and water mixture.

Refinement top

The H atoms bonded to O5 were located in difference Fourier maps and refined independently. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.93 Å for aromatic H atoms, 0.96 Å for methyl H atoms, 0.97 Å for CH2, 0.98 Å for CH and 0.82 Å for the phenolic OH group. Uiso(H) values were set at 1.2 times Ueq(C) for aromatic C, the CH2 group and the CH group respectively, and 1.5 times Ueq(O) or Ueq(C) for phenolic OH group and the CH3 group.

Structure description top

Flavonoids are a large group of phenolic plant constituents. Approximately 9000 different flavonoids from different plant sources have been described so far, and each year, hundreds of newly identified flavonoids are being recorded in the literature (Xiao, et al., 2011). Extensive epidemiological studies and in vitro experiments with polyphenols have indicate their broad variety of biological activities, including anticancer, anti-inflammatory, antibacterial, cardioprotective and enzyme-inhibitory activities (Xiao, et al., 2007,2010).

The title compound crystallizes as a hydrate (Fig. 1). The C4-C9 ring forms a dihedral angle of 71.4 (6) ° with the C10-C15 ring. In the pyran ring, atoms C2-C4/C9/O1 are essentially planar with a mean deviation of 0.0115 Å and C1 is 0.535 (2) Å from the plane of these atoms.

In the crystal, O—H···O hydrogen bonds connect the components into a two-dimensional network parallel to (010) incorparating C22(4) and C22(11) chains. In addtion, weak C—H···O, C—H···π(ring) interactions and π–π stacking interactions with a centroid to centroid distance of 3.768 (2) Å are present.

For background to and the biological activity of flavonoids, see: Xiao et al. (2007, 2010, 2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure with hydrogen bonds and other weak interactions shown as dashed lines. Only H atoms involved in hydrogen bonds are shown.
3-(4-Hydroxyphenyl)-7-methoxychroman-4-one monohydrate top
Crystal data top
C16H14O4·H2OF(000) = 608
Mr = 288.29Dx = 1.330 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2114 reflections
a = 9.730 (3) Åθ = 2.7–26.4°
b = 17.977 (5) ŵ = 0.10 mm−1
c = 8.570 (2) ÅT = 296 K
β = 106.194 (2)°Block, colorless
V = 1439.6 (6) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		3113 independent reflections
Radiation source: fine-focus sealed tube2019 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.971, Tmax = 0.981k = −22→22
11487 measured reflectionsl = −10→10
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0538P)2 + 0.3767P]
where P = (Fo2 + 2Fc2)/3
3113 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C16H14O4·H2OV = 1439.6 (6) Å3
Mr = 288.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.730 (3) ŵ = 0.10 mm−1
b = 17.977 (5) ÅT = 296 K
c = 8.570 (2) Å0.30 × 0.20 × 0.20 mm
β = 106.194 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer		3113 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2019 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.981Rint = 0.031
11487 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.33 e Å−3
3113 reflectionsΔρmin = −0.16 e Å−3
200 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
xyzUiso*/Ueq
C10.2951 (2)1.04367 (12)0.2561 (3)0.0630 (6)
H1A0.32891.03110.37050.076*
H1B0.37221.06910.22670.076*
C20.2612 (2)0.97338 (12)0.1596 (3)0.0559 (5)
H20.23480.98740.04450.067*
C30.1304 (2)0.93648 (12)0.1916 (3)0.0541 (5)
C40.03218 (19)0.98545 (10)0.2438 (2)0.0454 (5)
C5−0.0930 (2)0.95830 (11)0.2750 (2)0.0515 (5)
H5−0.11030.90740.26980.062*
C6−0.1897 (2)1.00472 (11)0.3125 (3)0.0529 (5)
H6−0.27200.98550.33250.064*
C7−0.1647 (2)1.08125 (12)0.3209 (2)0.0506 (5)
C8−0.0416 (2)1.11027 (11)0.2938 (3)0.0540 (5)
H8−0.02461.16120.30000.065*
C90.0559 (2)1.06186 (11)0.2570 (2)0.0482 (5)
C100.3882 (2)0.92093 (11)0.1881 (3)0.0499 (5)
C110.4480 (2)0.90321 (12)0.0668 (3)0.0569 (5)
H110.41230.9252−0.03470.068*
C120.5599 (2)0.85359 (12)0.0907 (3)0.0568 (5)
H120.59820.84210.00560.068*
C130.6149 (2)0.82111 (11)0.2404 (3)0.0523 (5)
C140.5584 (2)0.83907 (12)0.3660 (3)0.0587 (6)
H140.59630.81810.46810.070*
C150.4451 (2)0.88844 (12)0.3398 (3)0.0577 (6)
H150.40660.90000.42460.069*
C16−0.2487 (3)1.20180 (15)0.3705 (4)0.0983 (10)
H16A−0.16301.21330.45450.147*
H16B−0.32941.22400.39620.147*
H16C−0.24111.22110.26880.147*
H5A0.949 (3)0.8105 (17)0.083 (3)0.093 (9)*
H5B0.832 (4)0.764 (2)−0.042 (6)0.162 (16)*
O10.17584 (15)1.09344 (8)0.2323 (2)0.0641 (4)
O20.10853 (16)0.87006 (9)0.1665 (2)0.0805 (6)
O3−0.26743 (16)1.12282 (8)0.3586 (2)0.0687 (5)
O40.72298 (18)0.76992 (10)0.2689 (2)0.0773 (5)
H40.76090.77110.19460.116*
O50.8803 (2)0.77481 (10)0.0708 (3)0.0741 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0498 (12)0.0499 (12)0.0940 (18)−0.0034 (10)0.0277 (12)−0.0004 (11)
C20.0477 (11)0.0605 (13)0.0574 (13)0.0027 (10)0.0113 (10)0.0015 (10)
C30.0419 (11)0.0472 (12)0.0660 (14)−0.0005 (9)0.0032 (10)−0.0042 (10)
C40.0413 (10)0.0439 (11)0.0468 (11)−0.0009 (8)0.0053 (9)0.0008 (8)
C50.0479 (11)0.0453 (11)0.0573 (13)−0.0062 (9)0.0080 (10)−0.0004 (9)
C60.0494 (11)0.0544 (12)0.0562 (13)−0.0063 (9)0.0166 (10)0.0014 (10)
C70.0499 (11)0.0540 (12)0.0492 (12)0.0061 (9)0.0160 (9)0.0016 (9)
C80.0583 (12)0.0409 (11)0.0648 (14)0.0025 (9)0.0206 (11)0.0047 (9)
C90.0451 (11)0.0453 (11)0.0539 (12)−0.0021 (9)0.0133 (9)0.0054 (9)
C100.0406 (10)0.0476 (11)0.0582 (13)−0.0005 (9)0.0083 (9)0.0035 (10)
C110.0540 (12)0.0622 (14)0.0508 (13)0.0036 (10)0.0086 (10)0.0074 (10)
C120.0581 (13)0.0614 (13)0.0520 (13)0.0040 (10)0.0170 (10)0.0025 (10)
C130.0458 (11)0.0469 (11)0.0625 (14)0.0035 (9)0.0123 (10)0.0042 (10)
C140.0630 (13)0.0591 (13)0.0521 (13)0.0042 (11)0.0128 (11)0.0113 (10)
C150.0571 (12)0.0606 (13)0.0607 (14)0.0006 (10)0.0252 (11)−0.0004 (11)
C160.102 (2)0.0595 (16)0.152 (3)0.0176 (15)0.067 (2)−0.0024 (17)
O10.0566 (9)0.0436 (8)0.0990 (12)−0.0018 (7)0.0331 (8)0.0061 (8)
O20.0518 (9)0.0526 (10)0.1353 (16)−0.0072 (7)0.0228 (10)−0.0261 (10)
O30.0678 (10)0.0585 (10)0.0898 (12)0.0046 (8)0.0385 (9)−0.0030 (8)
O40.0805 (11)0.0754 (11)0.0794 (12)0.0351 (9)0.0278 (9)0.0175 (9)
O50.0637 (11)0.0722 (12)0.0863 (14)−0.0155 (9)0.0206 (10)−0.0140 (10)
Geometric parameters (Å, º) top
C1—O11.434 (2)C9—O11.367 (2)
C1—C21.496 (3)C10—C111.363 (3)
C1—H1A0.9700C10—C151.392 (3)
C1—H1B0.9700C11—C121.378 (3)
C2—C101.519 (3)C11—H110.9300
C2—C31.527 (3)C12—C131.375 (3)
C2—H20.9800C12—H120.9300
C3—O21.221 (2)C13—O41.367 (2)
C3—C41.458 (3)C13—C141.376 (3)
C4—C91.392 (3)C14—C151.384 (3)
C4—C51.405 (3)C14—H140.9300
C5—C61.362 (3)C15—H150.9300
C5—H50.9300C16—O31.432 (3)
C6—C71.395 (3)C16—H16A0.9600
C6—H60.9300C16—H16B0.9600
C7—O31.357 (2)C16—H16C0.9600
C7—C81.384 (3)O4—H40.8200
C8—C91.386 (3)O5—H5A0.91 (3)
C8—H80.9300O5—H5B0.97 (5)
O1—C1—C2113.81 (18)O1—C9—C4121.74 (17)
O1—C1—H1A108.8C8—C9—C4121.99 (18)
C2—C1—H1A108.8C11—C10—C15118.12 (19)
O1—C1—H1B108.8C11—C10—C2121.57 (19)
C2—C1—H1B108.8C15—C10—C2120.30 (19)
H1A—C1—H1B107.7C10—C11—C12121.7 (2)
C1—C2—C10113.06 (17)C10—C11—H11119.1
C1—C2—C3109.50 (17)C12—C11—H11119.1
C10—C2—C3112.51 (17)C13—C12—C11120.0 (2)
C1—C2—H2107.1C13—C12—H12120.0
C10—C2—H2107.1C11—C12—H12120.0
C3—C2—H2107.1O4—C13—C12122.2 (2)
O2—C3—C4123.18 (19)O4—C13—C14118.25 (19)
O2—C3—C2120.41 (19)C12—C13—C14119.57 (19)
C4—C3—C2116.32 (18)C13—C14—C15119.8 (2)
C9—C4—C5117.36 (18)C13—C14—H14120.1
C9—C4—C3120.86 (17)C15—C14—H14120.1
C5—C4—C3121.71 (18)C14—C15—C10120.8 (2)
C6—C5—C4121.66 (19)C14—C15—H15119.6
C6—C5—H5119.2C10—C15—H15119.6
C4—C5—H5119.2O3—C16—H16A109.5
C5—C6—C7119.60 (19)O3—C16—H16B109.5
C5—C6—H6120.2H16A—C16—H16B109.5
C7—C6—H6120.2O3—C16—H16C109.5
O3—C7—C8124.17 (19)H16A—C16—H16C109.5
O3—C7—C6115.17 (18)H16B—C16—H16C109.5
C8—C7—C6120.66 (18)C9—O1—C1114.27 (15)
C7—C8—C9118.69 (18)C7—O3—C16118.38 (18)
C7—C8—H8120.7C13—O4—H4109.5
C9—C8—H8120.7H5A—O5—H5B113 (3)
O1—C9—C8116.26 (17)
O1—C1—C2—C10−179.23 (17)C5—C4—C9—C8−2.2 (3)
O1—C1—C2—C3−52.9 (2)C3—C4—C9—C8174.76 (19)
C1—C2—C3—O2−158.3 (2)C1—C2—C10—C11−115.6 (2)
C10—C2—C3—O2−31.6 (3)C3—C2—C10—C11119.7 (2)
C1—C2—C3—C425.1 (3)C1—C2—C10—C1565.6 (3)
C10—C2—C3—C4151.69 (18)C3—C2—C10—C15−59.1 (3)
O2—C3—C4—C9−174.3 (2)C15—C10—C11—C121.2 (3)
C2—C3—C4—C92.3 (3)C2—C10—C11—C12−177.6 (2)
O2—C3—C4—C52.6 (3)C10—C11—C12—C13−0.6 (3)
C2—C3—C4—C5179.13 (18)C11—C12—C13—O4178.0 (2)
C9—C4—C5—C61.7 (3)C11—C12—C13—C14−0.6 (3)
C3—C4—C5—C6−175.30 (19)O4—C13—C14—C15−177.44 (19)
C4—C5—C6—C7−0.1 (3)C12—C13—C14—C151.3 (3)
C5—C6—C7—O3179.76 (18)C13—C14—C15—C10−0.7 (3)
C5—C6—C7—C8−0.9 (3)C11—C10—C15—C14−0.5 (3)
O3—C7—C8—C9179.62 (19)C2—C10—C15—C14178.31 (19)
C6—C7—C8—C90.4 (3)C8—C9—O1—C1157.45 (19)
C7—C8—C9—O1−179.64 (19)C4—C9—O1—C1−23.4 (3)
C7—C8—C9—C41.2 (3)C2—C1—O1—C953.4 (3)
C5—C4—C9—O1178.69 (18)C8—C7—O3—C160.3 (3)
C3—C4—C9—O1−4.3 (3)C6—C7—O3—C16179.6 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C4–C9 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O4—H4···O50.821.782.585 (2)167
O5—H5A···O2i0.91 (3)1.86 (3)2.742 (3)163 (3)
O5—H5B···O4ii0.97 (5)1.78 (5)2.734 (3)168 (4)
C8—H8···O5iii0.932.553.397 (3)152
C2—H2···Cg1iv0.982.863.745 (3)151
C6—H6···Cg2v0.932.973.748 (3)142
Symmetry codes: (i) x+1, y, z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x, y+5/2, −z+1/2; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC16H14O4·H2O
Mr288.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.730 (3), 17.977 (5), 8.570 (2)
β (°) 106.194 (2)
V (Å3)1439.6 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.971, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		11487, 3113, 2019
Rint0.031
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.138, 1.04
No. of reflections3113
No. of parameters200
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.33, −0.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C4–C9 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O4—H4···O50.821.782.585 (2)166.7
O5—H5A···O2i0.91 (3)1.86 (3)2.742 (3)163 (3)
O5—H5B···O4ii0.97 (5)1.78 (5)2.734 (3)168 (4)
C8—H8···O5iii0.932.553.397 (3)151.8
C2—H2···Cg1iv0.982.863.745 (3)151
C6—H6···Cg2v0.932.973.748 (3)142
Symmetry codes: (i) x+1, y, z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) −x, y+5/2, −z+1/2; (v) x−1, y, z.
 

Acknowledgements

The work was financed by a project supported by Hunan Provincial Natural Science Foundation of China (grant No. 11JJ3113) and the Key Laboratory of Ecotourism Application Technology, Hunan Province (grant No. JDSTLY01103).

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXiao, Z.-P., Ma, T.-W., Fu, W.-C., Peng, X.-C., Zhang, A.-H. & Zhu, H.-L. (2010). Eur. J. Med. Chem. 45, 5064–5070.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationXiao, Z.-P., Peng, Z.-Y., Peng, M.-J., Yan, W.-B., Ouyang, Y.-Z. & Zhu, H.-L. (2011). Mini-rev. Med. Chem. 11, 169–177.  Web of Science CrossRef CAS Google Scholar
 First citationXiao, Z.-P., Xue, J.-Y., Tan, S.-H., Li, H.-Q. & Zhu, H.-L. (2007). Bioorg. Med. Chem. 15, 4212–4219.  Web of Science CSD CrossRef PubMed CAS 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3212
https://doi.org/10.1107/S1600536811046034
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS