5-Hy-droxy-6-[(E)-2-phenyl-ethen-yl]-5,6-dihydro-2H-pyran-2-one isolated from Goniothalamus ridleyi.

In the title compound, C(13)H(12)O(3), the pyran ring adopts a half-chair conformation with a C atom deviating from the least-squares plane of the remaining ring atoms by 0.606 (2) Å. This plane and that of the benzene ring make a dihedral angle of 44.18 (6)°. In the crystal, mol-ecules are linked through O-H⋯O hydrogen bonds into infinite chains along the b axis, and these chains are cross-linked by C-H⋯O hydrogen bonded into sheets lying parallel to the bc plane. The layers are further connected via C-H⋯π inter-actions to form a three-dimensional supra-molecular structure.

Related literature

For spectroscopic characterization of the 5β-hy­droxy­goniothalamin, see: Goh et al. (1995 ▶). For the crystal structures of some similar compounds, see: Fun et al. (1995 ▶); Tuchinda et al. (2006 ▶).

Experimental

Crystal data

C13H12O3

M = 216.23

Monoclinic,

a = 6.5442 (8) Å

b = 11.0267 (14) Å

c = 8.0991 (10) Å

β = 111.402 (2)°

V = 544.14 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.18 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.973, T max = 0.994

2559 measured reflections

1250 independent reflections

1220 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.069

S = 1.08

1250 reflections

148 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028334/pv2562sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028334/pv2562Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028334/pv2562Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H12O3	F(000) = 228
Mr = 216.23	Dx = 1.320 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1643 reflections
a = 6.5442 (8) Å	θ = 2.7–29.6°
b = 11.0267 (14) Å	µ = 0.09 mm−1
c = 8.0991 (10) Å	T = 100 K
β = 111.402 (2)°	Plate, colorless
V = 544.14 (12) Å3	0.30 × 0.18 × 0.06 mm
Z = 2

Bruker APEXII CCD diffractometer	1250 independent reflections
Radiation source: fine-focus sealed tube	1220 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
φ and ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.973, Tmax = 0.994	k = −12→14
2559 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0382P)2 + 0.0929P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1250 reflections	Δρmax = 0.18 e Å−3
148 parameters	Δρmin = −0.18 e Å−3
1 restraint	Absolute structure: 749 Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
O1	0.6604 (2)	0.26455 (12)	−0.01641 (17)	0.0203 (3)
H1A	0.720 (4)	0.194 (2)	−0.012 (3)	0.024*
O2	0.12430 (19)	0.53996 (12)	−0.04165 (17)	0.0225 (3)
O3	0.46365 (18)	0.48046 (11)	0.10232 (16)	0.0185 (3)
C1	1.2436 (3)	0.59025 (18)	0.3976 (2)	0.0217 (4)
H1	1.1293	0.6247	0.2994	0.026*
C2	1.4539 (3)	0.63794 (18)	0.4495 (2)	0.0248 (4)
H2	1.4827	0.7041	0.3862	0.030*
C3	1.6224 (3)	0.58916 (18)	0.5938 (3)	0.0237 (4)
H3	1.7666	0.6215	0.6292	0.028*
C4	1.5782 (3)	0.49275 (18)	0.6858 (2)	0.0221 (4)
H4	1.6928	0.4591	0.7846	0.027*
C5	1.3677 (3)	0.44522 (17)	0.6346 (2)	0.0187 (3)
H5	1.3388	0.3801	0.6997	0.022*
C6	1.1977 (3)	0.49255 (16)	0.4877 (2)	0.0173 (3)
C7	0.9754 (3)	0.43928 (17)	0.4324 (2)	0.0191 (3)
H7	0.9309	0.4056	0.5219	0.023*
C8	0.8338 (3)	0.43534 (17)	0.2661 (2)	0.0186 (3)
H8	0.8795	0.4654	0.1752	0.022*
C9	0.6060 (3)	0.38607 (15)	0.2147 (2)	0.0172 (3)
H9	0.5705	0.3771	0.3242	0.021*
C10	0.5697 (2)	0.26443 (16)	0.1191 (2)	0.0176 (3)
H10	0.6423	0.1994	0.2070	0.021*
C11	0.3265 (3)	0.23880 (16)	0.0389 (2)	0.0200 (4)
H11	0.2771	0.1573	0.0154	0.024*
C12	0.1802 (3)	0.32814 (17)	0.0004 (2)	0.0203 (4)
H12	0.0282	0.3092	−0.0406	0.024*
C13	0.2497 (3)	0.45594 (16)	0.0204 (2)	0.0179 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0233 (6)	0.0155 (6)	0.0254 (6)	0.0005 (5)	0.0130 (5)	−0.0002 (5)
O2	0.0178 (6)	0.0187 (6)	0.0302 (7)	0.0013 (5)	0.0079 (5)	0.0025 (5)
O3	0.0136 (5)	0.0159 (6)	0.0237 (6)	−0.0004 (4)	0.0040 (4)	0.0009 (5)
C1	0.0229 (8)	0.0214 (9)	0.0180 (8)	0.0008 (7)	0.0042 (6)	0.0000 (7)
C2	0.0290 (9)	0.0222 (9)	0.0257 (9)	−0.0061 (8)	0.0130 (8)	−0.0031 (8)
C3	0.0175 (7)	0.0268 (10)	0.0282 (9)	−0.0057 (7)	0.0099 (7)	−0.0106 (8)
C4	0.0189 (8)	0.0226 (9)	0.0217 (8)	0.0044 (7)	0.0035 (6)	−0.0045 (7)
C5	0.0197 (8)	0.0184 (8)	0.0180 (8)	0.0023 (7)	0.0068 (6)	−0.0011 (7)
C6	0.0160 (7)	0.0180 (8)	0.0180 (7)	0.0004 (7)	0.0062 (6)	−0.0035 (7)
C7	0.0182 (8)	0.0184 (8)	0.0217 (8)	0.0001 (7)	0.0084 (7)	−0.0003 (7)
C8	0.0162 (7)	0.0177 (8)	0.0224 (8)	−0.0008 (7)	0.0078 (6)	−0.0008 (7)
C9	0.0161 (8)	0.0175 (8)	0.0179 (8)	0.0010 (6)	0.0059 (6)	0.0021 (6)
C10	0.0171 (7)	0.0154 (8)	0.0208 (8)	−0.0001 (6)	0.0075 (6)	0.0022 (7)
C11	0.0205 (8)	0.0163 (8)	0.0230 (8)	−0.0046 (7)	0.0077 (7)	−0.0006 (7)
C12	0.0128 (7)	0.0220 (9)	0.0241 (8)	−0.0039 (7)	0.0044 (7)	0.0003 (7)
C13	0.0153 (7)	0.0195 (9)	0.0204 (8)	−0.0005 (7)	0.0081 (6)	0.0005 (7)

O1—C10	1.426 (2)	C5—H5	0.9500
O1—H1A	0.87 (3)	C6—C7	1.479 (2)
O2—C13	1.218 (2)	C7—C8	1.328 (2)
O3—C13	1.3399 (19)	C7—H7	0.9500
O3—C9	1.470 (2)	C8—C9	1.496 (2)
C1—C2	1.387 (2)	C8—H8	0.9500
C1—C6	1.394 (3)	C9—C10	1.523 (2)
C1—H1	0.9500	C9—H9	1.0000
C2—C3	1.390 (3)	C10—C11	1.510 (2)
C2—H2	0.9500	C10—H10	1.0000
C3—C4	1.388 (3)	C11—C12	1.329 (2)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.388 (2)	C12—C13	1.471 (2)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.400 (2)
C10—O1—H1A	106.0 (15)	C7—C8—H8	118.3
C13—O3—C9	118.37 (13)	C9—C8—H8	118.3
C2—C1—C6	120.93 (16)	O3—C9—C8	104.91 (13)
C2—C1—H1	119.5	O3—C9—C10	111.27 (13)
C6—C1—H1	119.5	C8—C9—C10	114.59 (14)
C1—C2—C3	120.21 (18)	O3—C9—H9	108.6
C1—C2—H2	119.9	C8—C9—H9	108.6
C3—C2—H2	119.9	C10—C9—H9	108.6
C4—C3—C2	119.41 (16)	O1—C10—C11	109.78 (13)
C4—C3—H3	120.3	O1—C10—C9	111.02 (14)
C2—C3—H3	120.3	C11—C10—C9	109.15 (14)
C3—C4—C5	120.46 (16)	O1—C10—H10	109.0
C3—C4—H4	119.8	C11—C10—H10	109.0
C5—C4—H4	119.8	C9—C10—H10	109.0
C4—C5—C6	120.50 (16)	C12—C11—C10	121.20 (16)
C4—C5—H5	119.8	C12—C11—H11	119.4
C6—C5—H5	119.8	C10—C11—H11	119.4
C1—C6—C5	118.47 (15)	C11—C12—C13	121.12 (14)
C1—C6—C7	121.66 (15)	C11—C12—H12	119.4
C5—C6—C7	119.87 (15)	C13—C12—H12	119.4
C8—C7—C6	124.42 (16)	O2—C13—O3	118.41 (16)
C8—C7—H7	117.8	O2—C13—C12	123.25 (15)
C6—C7—H7	117.8	O3—C13—C12	118.22 (14)
C7—C8—C9	123.36 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.87 (3)	1.95 (3)	2.8026 (19)	170 (2)
C12—H12···O1ii	0.95	2.53	3.427 (2)	157
C9—H9···Cgii	1.00	2.97	3.747 (2)	135
C10—H10···Cgiii	1.00	2.80	3.6561 (18)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.87 (3)	1.95 (3)	2.8026 (19)	170 (2)
C12—H12⋯O1ii	0.95	2.53	3.427 (2)	157
C9—H9⋯Cg ii	1.00	2.97	3.747 (2)	135
C10—H10⋯Cg iii	1.00	2.80	3.6561 (18)	144

Symmetry codes: (i) ; (ii) ; (iii) .