Glabridin

Tantishaiyakul, V.; Suknuntha, K.; Saithong, S.; Pakawatchai, C.

doi:10.1107/S1600536812048647

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3501

doi:10.1107/S1600536812048647

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Glabridin

Vimon Tantishaiyakul,^a ^* Krit Suknuntha,^a Saowanit Saithong ^b and Chaveng Pakawatchai ^b

^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

(Received 11 November 2012; accepted 27 November 2012; online 30 November 2012)

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 envelope conformation, 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 absolute structure 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 absolute structure, see: Kim et al. (2009 ).

Experimental

Crystal data

C₂₀H₂₀O₄
M_r = 324.36
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.4301 (4) Å
b = 12.0307 (7) Å
c = 21.0690 (13) Å
V = 1629.87 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.14 × 0.07 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.984, T_max = 0.994
15459 measured reflections
2866 independent reflections
2551 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.095
S = 1.16
2866 reflections
225 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{5\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); 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: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812048647/hb6989sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048647/hb6989Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048647/hb6989Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 absolute structure, see: Kim et al. (2009).

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 1998); 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: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	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.

4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen- 3-yl]benzene-1,3-diol top

Crystal data top

C₂₀H₂₀O₄	F(000) = 688
M_r = 324.36	D_x = 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

Data collection top

Bruker APEX CCD diffractometer	2866 independent reflections
Radiation source: fine-focus sealed tube	2551 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Frames, each covering 0.3 ° in ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −7→7
T_min = 0.984, T_max = 0.994	k = −14→14
15459 measured reflections	l = −25→25

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)] = 0.046	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(F_o²) + (0.0365P)² + 0.2296P] where P = (F_o² + 2F_c²)/3
2866 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.15 e Å⁻³
2 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₀H₂₀O₄	V = 1629.87 (17) Å³
M_r = 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

Data collection top

Bruker APEX CCD diffractometer	2866 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2551 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.994	R_int = 0.045
15459 measured reflections

Refinement top

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	Δρ_max = 0.15 e Å⁻³
2866 reflections	Δρ_min = −0.17 e Å⁻³
225 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 > 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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.984, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	15459, 2866, 2551
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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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Volume 68| Part 12| December 2012| Page o3501

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