organic compounds
Glabridin
aDepartment of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University and Nanotec-PSU Center of Excellence for Drug Delivery Systems, Hat-Yai, Songkhla 90112, Thailand, and bDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: vimon.t@psu.ac.th
In the title compound, C20H20O4 {systematic name: 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol}, the hydropyran ring linked to the pendant benzene ring adopts an with the methyne C atom forming the flap. In the crystal, the –OH group at the 3-position of the benzene ring forms an O—H⋯O hydrogen bond to a chromene O-atom acceptor, whereas the –OH group at the 1-position forms an O—H⋯π interaction with a neighboring benzene ring. The O—H⋯O hydrogen bonds form [001] chains and the O—H⋯π bonds cross-link the chains into (101) sheets. The was assumed to be the same as that deduced from previous studies for the natural product.
Related literature
For background to the pharmacological activity of the title compound, see: Fukai et al. (2000); Messier & Grenier; (2011); Thiyagarajan et al. (2011); Ahn et al. (2012); Choi (2005). For the assignment of the see: Kim et al. (2009).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell 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: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812048647/hb6989sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048647/hb6989Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812048647/hb6989Isup3.cml
The title compound was obtained from Nanjing Zelang Medical Technology Co. Ltd. Colourless blocks were obtained by dissolving the compound in methanol followed by a slow evaporation of the solvent.
Amonalous dispersion was found to be negligible and the
is indeterminate. Friedel pairs were merged before the final H atoms on carbon atoms were positioned geometrically and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C-sp2) with C—H = 0.93 Å and 1.5Ueq(C-sp3) with the distances ranging from 0.96 to 0.98 Å, respectively. The H atoms on the oxygen atoms were located in a difference Fourier map and restrained with Uiso(H) = 1.2Ueq(OH). (O—H = 0.80 (2) and 0.82 (2) Å).Data collection: SMART (Bruker, 1998); cell
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: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound. | |
Fig. 2. The packing of the intermolecular interactions of the title compound is plotted down a axis. |
C20H20O4 | F(000) = 688 |
Mr = 324.36 | Dx = 1.322 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2104 reflections |
a = 6.4301 (4) Å | θ = 3.3–21.0° |
b = 12.0307 (7) Å | µ = 0.09 mm−1 |
c = 21.0690 (13) Å | T = 293 K |
V = 1629.87 (17) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.14 × 0.07 mm |
Bruker APEX CCD diffractometer | 2866 independent reflections |
Radiation source: fine-focus sealed tube | 2551 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Frames, each covering 0.3 ° in ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −7→7 |
Tmin = 0.984, Tmax = 0.994 | k = −14→14 |
15459 measured reflections | l = −25→25 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0365P)2 + 0.2296P] where P = (Fo2 + 2Fc2)/3 |
2866 reflections | (Δ/σ)max < 0.001 |
225 parameters | Δρmax = 0.15 e Å−3 |
2 restraints | Δρmin = −0.17 e Å−3 |
C20H20O4 | V = 1629.87 (17) Å3 |
Mr = 324.36 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.4301 (4) Å | µ = 0.09 mm−1 |
b = 12.0307 (7) Å | T = 293 K |
c = 21.0690 (13) Å | 0.22 × 0.14 × 0.07 mm |
Bruker APEX CCD diffractometer | 2866 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 2551 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.994 | Rint = 0.045 |
15459 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 2 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 0.15 e Å−3 |
2866 reflections | Δρmin = −0.17 e Å−3 |
225 parameters |
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 > 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.7767 (3) | 0.66156 (13) | 0.23880 (7) | 0.0443 (4) | |
O2 | 1.0695 (3) | 0.80853 (13) | 0.05050 (7) | 0.0477 (5) | |
C1 | 0.9085 (4) | 0.56254 (19) | 0.23598 (11) | 0.0417 (6) | |
C2 | 1.1009 (4) | 0.5878 (2) | 0.19907 (11) | 0.0458 (6) | |
H2 | 1.2221 | 0.5486 | 0.2080 | 0.055* | |
C3 | 1.1042 (4) | 0.6644 (2) | 0.15409 (11) | 0.0424 (6) | |
H3 | 1.2243 | 0.6754 | 0.1303 | 0.051* | |
C4 | 0.9211 (4) | 0.73112 (18) | 0.14167 (10) | 0.0326 (5) | |
C5 | 0.7586 (4) | 0.72632 (18) | 0.18500 (10) | 0.0370 (6) | |
C6 | 0.5850 (4) | 0.7914 (2) | 0.17877 (12) | 0.0479 (6) | |
H6 | 0.4783 | 0.7876 | 0.2085 | 0.057* | |
C7 | 0.5712 (4) | 0.8631 (2) | 0.12745 (12) | 0.0466 (6) | |
H7 | 0.4530 | 0.9070 | 0.1230 | 0.056* | |
C8 | 0.7277 (4) | 0.87146 (18) | 0.08254 (11) | 0.0366 (5) | |
C9 | 0.9013 (4) | 0.80460 (18) | 0.09051 (10) | 0.0340 (5) | |
C10 | 1.0643 (4) | 0.88701 (19) | −0.00121 (10) | 0.0431 (6) | |
H10A | 1.0019 | 0.8517 | −0.0380 | 0.052* | |
H10B | 1.2055 | 0.9076 | −0.0123 | 0.052* | |
C11 | 0.9426 (4) | 0.99118 (18) | 0.01485 (10) | 0.0357 (5) | |
H11 | 1.0017 | 1.0217 | 0.0540 | 0.043* | |
C12 | 0.7201 (4) | 0.95505 (19) | 0.02970 (12) | 0.0435 (6) | |
H12A | 0.6376 | 1.0188 | 0.0424 | 0.052* | |
H12B | 0.6567 | 0.9223 | −0.0076 | 0.052* | |
C13 | 0.9633 (4) | 1.07917 (18) | −0.03561 (10) | 0.0353 (5) | |
C14 | 1.1391 (4) | 1.14759 (18) | −0.03656 (10) | 0.0364 (6) | |
C15 | 1.1636 (4) | 1.23098 (19) | −0.08114 (11) | 0.0378 (5) | |
H15 | 1.2811 | 1.2760 | −0.0802 | 0.045* | |
C16 | 1.0135 (4) | 1.24727 (18) | −0.12703 (10) | 0.0372 (6) | |
C17 | 0.8386 (4) | 1.1812 (2) | −0.12775 (11) | 0.0449 (6) | |
H17 | 0.7366 | 1.1918 | −0.1585 | 0.054* | |
C18 | 0.8159 (4) | 1.09882 (19) | −0.08240 (11) | 0.0425 (6) | |
H18 | 0.6970 | 1.0549 | −0.0833 | 0.051* | |
C19 | 0.9574 (5) | 0.5352 (3) | 0.30460 (12) | 0.0639 (8) | |
H19A | 1.0368 | 0.5946 | 0.3230 | 0.096* | |
H19B | 1.0363 | 0.4675 | 0.3065 | 0.096* | |
H19C | 0.8300 | 0.5261 | 0.3278 | 0.096* | |
C20 | 0.7812 (6) | 0.4713 (2) | 0.20419 (15) | 0.0721 (9) | |
H20A | 0.6555 | 0.4593 | 0.2278 | 0.108* | |
H20B | 0.8608 | 0.4038 | 0.2031 | 0.108* | |
H20C | 0.7472 | 0.4934 | 0.1617 | 0.108* | |
O3 | 1.2858 (3) | 1.12753 (14) | 0.00917 (9) | 0.0536 (5) | |
H3A | 1.362 (4) | 1.1797 (18) | 0.0133 (14) | 0.064* | |
O4 | 1.0477 (3) | 1.33015 (16) | −0.16975 (8) | 0.0551 (5) | |
H4A | 0.957 (4) | 1.334 (2) | −0.1969 (11) | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0529 (11) | 0.0443 (9) | 0.0356 (9) | 0.0025 (8) | 0.0083 (8) | 0.0037 (8) |
O2 | 0.0485 (11) | 0.0493 (10) | 0.0452 (9) | 0.0166 (9) | 0.0169 (9) | 0.0160 (8) |
C1 | 0.0460 (15) | 0.0360 (13) | 0.0431 (13) | −0.0006 (11) | 0.0002 (13) | 0.0026 (11) |
C2 | 0.0429 (16) | 0.0503 (15) | 0.0443 (14) | 0.0106 (13) | 0.0013 (12) | 0.0064 (12) |
C3 | 0.0391 (14) | 0.0493 (14) | 0.0389 (13) | 0.0042 (12) | 0.0071 (12) | 0.0038 (12) |
C4 | 0.0349 (12) | 0.0318 (11) | 0.0312 (11) | −0.0027 (10) | 0.0009 (11) | −0.0031 (10) |
C5 | 0.0418 (14) | 0.0341 (12) | 0.0351 (12) | −0.0048 (11) | 0.0001 (11) | −0.0035 (10) |
C6 | 0.0435 (15) | 0.0524 (15) | 0.0479 (14) | 0.0039 (13) | 0.0142 (13) | 0.0032 (12) |
C7 | 0.0337 (14) | 0.0463 (14) | 0.0598 (15) | 0.0073 (12) | 0.0054 (13) | 0.0070 (13) |
C8 | 0.0328 (13) | 0.0336 (12) | 0.0433 (13) | −0.0014 (11) | −0.0025 (12) | −0.0027 (11) |
C9 | 0.0347 (13) | 0.0339 (11) | 0.0335 (12) | −0.0036 (10) | 0.0048 (11) | −0.0061 (10) |
C10 | 0.0521 (15) | 0.0446 (13) | 0.0326 (12) | 0.0064 (12) | 0.0058 (12) | 0.0053 (11) |
C11 | 0.0381 (13) | 0.0372 (12) | 0.0319 (12) | 0.0005 (11) | −0.0050 (11) | −0.0018 (10) |
C12 | 0.0403 (15) | 0.0419 (13) | 0.0482 (14) | 0.0067 (12) | −0.0014 (12) | 0.0038 (12) |
C13 | 0.0405 (14) | 0.0350 (12) | 0.0304 (12) | 0.0018 (11) | −0.0035 (11) | −0.0038 (10) |
C14 | 0.0383 (14) | 0.0353 (12) | 0.0355 (12) | 0.0014 (11) | −0.0093 (11) | −0.0044 (11) |
C15 | 0.0370 (14) | 0.0352 (12) | 0.0413 (12) | −0.0063 (11) | −0.0006 (11) | −0.0031 (11) |
C16 | 0.0463 (15) | 0.0352 (12) | 0.0302 (12) | 0.0006 (12) | −0.0021 (11) | −0.0016 (10) |
C17 | 0.0506 (16) | 0.0469 (14) | 0.0372 (13) | −0.0027 (13) | −0.0152 (12) | 0.0017 (12) |
C18 | 0.0447 (15) | 0.0426 (13) | 0.0402 (13) | −0.0106 (12) | −0.0083 (13) | 0.0005 (12) |
C19 | 0.067 (2) | 0.076 (2) | 0.0484 (16) | 0.0029 (18) | 0.0022 (16) | 0.0185 (15) |
C20 | 0.086 (2) | 0.0478 (16) | 0.082 (2) | −0.0106 (18) | −0.008 (2) | −0.0059 (16) |
O3 | 0.0471 (11) | 0.0522 (11) | 0.0616 (11) | −0.0086 (9) | −0.0261 (10) | 0.0097 (10) |
O4 | 0.0654 (13) | 0.0539 (11) | 0.0462 (10) | −0.0134 (11) | −0.0119 (9) | 0.0168 (9) |
O1—C5 | 1.380 (3) | C11—C12 | 1.528 (3) |
O1—C1 | 1.463 (3) | C11—H11 | 0.9800 |
O2—C9 | 1.372 (3) | C12—H12A | 0.9700 |
O2—C10 | 1.442 (2) | C12—H12B | 0.9700 |
C1—C2 | 1.493 (4) | C13—C18 | 1.388 (3) |
C1—C19 | 1.516 (3) | C13—C14 | 1.398 (3) |
C1—C20 | 1.524 (4) | C14—O3 | 1.369 (3) |
C2—C3 | 1.321 (3) | C14—C15 | 1.383 (3) |
C2—H2 | 0.9300 | C15—C16 | 1.380 (3) |
C3—C4 | 1.449 (3) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—O4 | 1.361 (3) |
C4—C5 | 1.389 (3) | C16—C17 | 1.377 (3) |
C4—C9 | 1.400 (3) | C17—C18 | 1.384 (3) |
C5—C6 | 1.370 (3) | C17—H17 | 0.9300 |
C6—C7 | 1.386 (3) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—H19A | 0.9600 |
C7—C8 | 1.385 (3) | C19—H19B | 0.9600 |
C7—H7 | 0.9300 | C19—H19C | 0.9600 |
C8—C9 | 1.386 (3) | C20—H20A | 0.9600 |
C8—C12 | 1.501 (3) | C20—H20B | 0.9600 |
C10—C11 | 1.516 (3) | C20—H20C | 0.9600 |
C10—H10A | 0.9700 | O3—H3A | 0.802 (17) |
C10—H10B | 0.9700 | O4—H4A | 0.820 (17) |
C11—C13 | 1.506 (3) | ||
C5—O1—C1 | 118.37 (17) | C13—C11—H11 | 107.3 |
C9—O2—C10 | 117.92 (18) | C10—C11—H11 | 107.3 |
O1—C1—C2 | 109.58 (18) | C12—C11—H11 | 107.3 |
O1—C1—C19 | 105.0 (2) | C8—C12—C11 | 108.17 (19) |
C2—C1—C19 | 111.7 (2) | C8—C12—H12A | 110.1 |
O1—C1—C20 | 107.1 (2) | C11—C12—H12A | 110.1 |
C2—C1—C20 | 111.3 (2) | C8—C12—H12B | 110.1 |
C19—C1—C20 | 112.0 (2) | C11—C12—H12B | 110.1 |
C3—C2—C1 | 121.9 (2) | H12A—C12—H12B | 108.4 |
C3—C2—H2 | 119.0 | C18—C13—C14 | 116.2 (2) |
C1—C2—H2 | 119.0 | C18—C13—C11 | 124.1 (2) |
C2—C3—C4 | 120.2 (2) | C14—C13—C11 | 119.7 (2) |
C2—C3—H3 | 119.9 | O3—C14—C15 | 121.8 (2) |
C4—C3—H3 | 119.9 | O3—C14—C13 | 116.3 (2) |
C5—C4—C9 | 117.7 (2) | C15—C14—C13 | 121.9 (2) |
C5—C4—C3 | 118.02 (19) | C16—C15—C14 | 119.9 (2) |
C9—C4—C3 | 124.2 (2) | C16—C15—H15 | 120.0 |
C6—C5—O1 | 118.1 (2) | C14—C15—H15 | 120.0 |
C6—C5—C4 | 121.8 (2) | O4—C16—C17 | 123.2 (2) |
O1—C5—C4 | 120.0 (2) | O4—C16—C15 | 117.0 (2) |
C5—C6—C7 | 118.9 (2) | C17—C16—C15 | 119.8 (2) |
C5—C6—H6 | 120.6 | C16—C17—C18 | 119.5 (2) |
C7—C6—H6 | 120.6 | C16—C17—H17 | 120.3 |
C8—C7—C6 | 122.1 (2) | C18—C17—H17 | 120.3 |
C8—C7—H7 | 118.9 | C17—C18—C13 | 122.7 (2) |
C6—C7—H7 | 118.9 | C17—C18—H18 | 118.7 |
C7—C8—C9 | 117.4 (2) | C13—C18—H18 | 118.7 |
C7—C8—C12 | 122.1 (2) | C1—C19—H19A | 109.5 |
C9—C8—C12 | 120.3 (2) | C1—C19—H19B | 109.5 |
O2—C9—C8 | 122.7 (2) | H19A—C19—H19B | 109.5 |
O2—C9—C4 | 115.1 (2) | C1—C19—H19C | 109.5 |
C8—C9—C4 | 122.2 (2) | H19A—C19—H19C | 109.5 |
O2—C10—C11 | 112.64 (17) | H19B—C19—H19C | 109.5 |
O2—C10—H10A | 109.1 | C1—C20—H20A | 109.5 |
C11—C10—H10A | 109.1 | C1—C20—H20B | 109.5 |
O2—C10—H10B | 109.1 | H20A—C20—H20B | 109.5 |
C11—C10—H10B | 109.1 | C1—C20—H20C | 109.5 |
H10A—C10—H10B | 107.8 | H20A—C20—H20C | 109.5 |
C13—C11—C10 | 112.19 (18) | H20B—C20—H20C | 109.5 |
C13—C11—C12 | 115.3 (2) | C14—O3—H3A | 111 (2) |
C10—C11—C12 | 107.10 (19) | C16—O4—H4A | 113 (2) |
C5—O1—C1—C2 | 40.3 (3) | C3—C4—C9—O2 | 1.3 (3) |
C5—O1—C1—C19 | 160.4 (2) | C5—C4—C9—C8 | 0.3 (3) |
C5—O1—C1—C20 | −80.5 (3) | C3—C4—C9—C8 | −176.3 (2) |
O1—C1—C2—C3 | −28.0 (3) | C9—O2—C10—C11 | 31.4 (3) |
C19—C1—C2—C3 | −143.8 (3) | O2—C10—C11—C13 | 171.8 (2) |
C20—C1—C2—C3 | 90.2 (3) | O2—C10—C11—C12 | −60.7 (3) |
C1—C2—C3—C4 | 3.5 (4) | C7—C8—C12—C11 | 147.1 (2) |
C2—C3—C4—C5 | 11.3 (3) | C9—C8—C12—C11 | −28.3 (3) |
C2—C3—C4—C9 | −172.2 (2) | C13—C11—C12—C8 | −177.54 (18) |
C1—O1—C5—C6 | 156.1 (2) | C10—C11—C12—C8 | 56.8 (2) |
C1—O1—C5—C4 | −29.1 (3) | C10—C11—C13—C18 | 99.2 (3) |
C9—C4—C5—C6 | −0.6 (3) | C12—C11—C13—C18 | −23.7 (3) |
C3—C4—C5—C6 | 176.2 (2) | C10—C11—C13—C14 | −81.4 (3) |
C9—C4—C5—O1 | −175.14 (19) | C12—C11—C13—C14 | 155.7 (2) |
C3—C4—C5—O1 | 1.7 (3) | C18—C13—C14—O3 | −179.3 (2) |
O1—C5—C6—C7 | 175.3 (2) | C11—C13—C14—O3 | 1.2 (3) |
C4—C5—C6—C7 | 0.6 (4) | C18—C13—C14—C15 | 0.7 (3) |
C5—C6—C7—C8 | −0.4 (4) | C11—C13—C14—C15 | −178.7 (2) |
C6—C7—C8—C9 | 0.2 (4) | O3—C14—C15—C16 | 179.0 (2) |
C6—C7—C8—C12 | −175.3 (2) | C13—C14—C15—C16 | −1.1 (3) |
C10—O2—C9—C8 | 0.9 (3) | C14—C15—C16—O4 | −179.5 (2) |
C10—O2—C9—C4 | −176.63 (19) | C14—C15—C16—C17 | 0.8 (3) |
C7—C8—C9—O2 | −177.5 (2) | O4—C16—C17—C18 | −179.9 (2) |
C12—C8—C9—O2 | −1.9 (3) | C15—C16—C17—C18 | −0.2 (3) |
C7—C8—C9—C4 | −0.2 (3) | C16—C17—C18—C13 | −0.2 (4) |
C12—C8—C9—C4 | 175.5 (2) | C14—C13—C18—C17 | −0.1 (3) |
C5—C4—C9—O2 | 177.88 (19) | C11—C13—C18—C17 | 179.3 (2) |
Cg4 is the centroid of the C13–C18 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O1i | 0.82 (2) | 2.02 (2) | 2.841 (3) | 177 (3) |
O3—H3A···Cg4ii | 0.80 (2) | 2.51 (2) | 3.213 (2) | 148 (3) |
Symmetry codes: (i) −x+3/2, −y+2, z−1/2; (ii) −x, y+5/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H20O4 |
Mr | 324.36 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 6.4301 (4), 12.0307 (7), 21.0690 (13) |
V (Å3) | 1629.87 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.22 × 0.14 × 0.07 |
Data collection | |
Diffractometer | Bruker APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.984, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15459, 2866, 2551 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.095, 1.16 |
No. of reflections | 2866 |
No. of parameters | 225 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.17 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).
Cg4 is the centroid of the C13–C18 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O1i | 0.82 (2) | 2.02 (2) | 2.841 (3) | 177 (3) |
O3—H3A···Cg4ii | 0.80 (2) | 2.51 (2) | 3.213 (2) | 148 (3) |
Symmetry codes: (i) −x+3/2, −y+2, z−1/2; (ii) −x, y+5/2, −z+1/2. |
Acknowledgements
Financial support by the Nanotechnology Center (NANOTEC), NSTDA, Ministry of Science and Technology, Thailand, through Center of Excellence Network program is gratefully acknowledged.
References
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4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol (Glabridin) is a pyranoisoflavan isolated from licorice. It has various pharmacological activities such as cytotoxic activity (Fukai et al., 2000), antimicrobial activity (Messier & Grenier, 2011), anti-inflammation (Thiyagarajan et al., 2011), anti-obesity effect (Ahn et al., 2012) and prevention for osteoporosis and inflammatory bone diseases (Choi, 2005). For the assignment of its absolute structure, see: Kim et al. (2009).
The molecular structure of the title compound is shown in Fig. 1. The packing features O—H···O intermolecular hydrogen bonding between hydroxyl group at 3 position of benzene ring with the donor-acceptor distance of 2.841 (3) Å. (O4—H4A···O1i; i: -x + 3/2, -y + 2, z - 1/2) forming a zigzag chains running parallel to the [001] direction. Besides, the O—H···π interactions with O···centroid distances of 3.213 (2) Å are observed between hydroxyl group at the 1 position of benzene ring and the nearby benzene ring of adjacent molecule, O3—H3A···Cg4ii (Cg4 is the centroid of C13—C14—C15—C16—C17—C18 and the symmetry code ii is -x, y + 5/2, -z + 1/2), linking among the zigzag chains generating two-dimensional layer parallel to (101) plane. The crystal packing of interaction is depicted in Fig. 2.