1-(5-Hy-droxy-2,2,8,8-tetra-methyl-2H,8H-pyrano[2,3-f]chromen-6-yl)ethanone.

In the title compound, C(18)H(20)O(4),the pyran ring of the chromene unit adopts a half-chair conformation. An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked along the b axis by C-H⋯O hydrogen bonds.

Related literature

The title compound is a precursor in the synthesis of biologically active prenylated chalcones, see: Adler & Baldwin (2009 ▶); Lee & Li (2007 ▶); For related structures, see: Lee & Xia (2007 ▶); Mondal et al. (2007 ▶); Narender et al. (2005 ▶).

Experimental

Crystal data

C18H20O4

M = 300.34

Triclinic,

a = 8.5039 (6) Å

b = 9.5370 (6) Å

c = 10.7859 (7) Å

α = 102.180 (3)°

β = 102.621 (3)°

γ = 110.671 (3)°

V = 757.86 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 446 K

0.39 × 0.21 × 0.2 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.965, T max = 0.982

17650 measured reflections

3770 independent reflections

3284 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.119

S = 1.06

3770 reflections

205 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204055X/hg5251sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204055X/hg5251Isup2.hkl

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

C18H20O4	Z = 2
Mr = 300.34	F(000) = 320
Triclinic, P1	Dx = 1.316 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5039 (6) Å	Cell parameters from 17650 reflections
b = 9.5370 (6) Å	θ = 2.0–28.5°
c = 10.7859 (7) Å	µ = 0.09 mm−1
α = 102.180 (3)°	T = 446 K
β = 102.621 (3)°	Block, yellow
γ = 110.671 (3)°	0.39 × 0.21 × 0.2 mm
V = 757.86 (9) Å3

Bruker SMART APEXII CCD diffractometer	3284 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 28.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→10
Tmin = 0.965, Tmax = 0.982	k = −12→12
17650 measured reflections	l = −14→14
3770 independent reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0701P)2 + 0.1777P] where P = (Fo2 + 2Fc2)/3
3770 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.96 Å for Me H atoms and 0.93 Å for aromatic H atoms; Uiso(H) = 1.2Ueq(C) (1.5 for Me groups)] and were included in the refinement in the riding model approximation. The O—H H-atom was located in a difference map and also placed in a calculated position O—H = 0.82 Å (Uiso(H) = 1.2Ueq(O).

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. >>> The Following Model ALERTS were generated - (Acta-Mode) <<< Format: alert-number_ALERT_alert-type_alert-level text 911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 5 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 62 154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 300 Deg. Noted:

	x	y	z	Uiso*/Ueq
C1	0.19888 (12)	0.60398 (11)	0.46668 (9)	0.01525 (19)
C2	0.20857 (12)	0.45580 (11)	0.43556 (9)	0.0169 (2)
C3	0.12126 (13)	0.33380 (11)	0.30439 (10)	0.0199 (2)
C4	0.01442 (14)	0.35565 (13)	0.18500 (10)	0.0252 (2)
H4A	−0.0205	0.2669	0.1072	0.038*
H4B	0.085	0.4506	0.1705	0.038*
H4C	−0.0894	0.3633	0.201	0.038*
C5	0.31333 (13)	0.42621 (11)	0.54112 (10)	0.0170 (2)
C6	0.40358 (12)	0.53801 (11)	0.66846 (9)	0.01595 (19)
C7	0.51498 (13)	0.51113 (11)	0.77598 (10)	0.0190 (2)
H7	0.5314	0.4184	0.7601	0.023*
C8	0.59305 (13)	0.61881 (12)	0.89653 (10)	0.0205 (2)
H8	0.6653	0.5995	0.9627	0.025*
C9	0.57082 (13)	0.77035 (12)	0.93170 (9)	0.0183 (2)
C10	0.47362 (16)	0.77313 (14)	1.03468 (11)	0.0279 (2)
H10A	0.4601	0.8703	1.0553	0.042*
H10B	0.5408	0.765	1.1147	0.042*
H10C	0.3588	0.6858	0.9989	0.042*
C11	0.74885 (14)	0.91349 (12)	0.98215 (11)	0.0250 (2)
H11A	0.8052	0.9128	0.9141	0.037*
H11B	0.8232	0.9096	1.0612	0.037*
H11C	0.7304	1.0083	1.003	0.037*
C12	0.38550 (12)	0.68003 (11)	0.69361 (9)	0.01523 (19)
C13	0.28325 (12)	0.71568 (11)	0.59435 (9)	0.01472 (19)
C14	0.25158 (12)	0.85820 (11)	0.61994 (9)	0.01643 (19)
H14	0.2817	0.9215	0.7074	0.02*
C15	0.17926 (12)	0.89745 (11)	0.51758 (9)	0.0176 (2)
H15	0.1525	0.9848	0.5333	0.021*
C16	0.14111 (12)	0.79960 (11)	0.37625 (9)	0.0174 (2)
C17	0.30306 (14)	0.85631 (13)	0.32954 (10)	0.0240 (2)
H17A	0.4006	0.8484	0.3875	0.036*
H17B	0.3348	0.9643	0.3322	0.036*
H17C	0.2755	0.7919	0.2396	0.036*
C18	−0.02224 (13)	0.79449 (13)	0.27938 (10)	0.0229 (2)
H18A	−0.0464	0.7254	0.192	0.034*
H18B	−0.001	0.8988	0.2749	0.034*
H18C	−0.1222	0.756	0.3101	0.034*
O1	0.09524 (9)	0.63381 (8)	0.36994 (7)	0.01782 (16)
O2	0.13363 (11)	0.20500 (9)	0.28795 (8)	0.02575 (18)
O3	0.33104 (10)	0.28943 (8)	0.52254 (7)	0.02275 (18)
H3	0.2748	0.2324	0.4451	0.034*
O4	0.46499 (10)	0.79211 (8)	0.81538 (7)	0.02102 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0132 (4)	0.0163 (4)	0.0162 (4)	0.0051 (3)	0.0054 (3)	0.0060 (3)
C2	0.0165 (4)	0.0147 (4)	0.0177 (4)	0.0042 (3)	0.0069 (3)	0.0039 (3)
C3	0.0171 (4)	0.0171 (4)	0.0214 (5)	0.0026 (4)	0.0089 (4)	0.0031 (4)
C4	0.0213 (5)	0.0244 (5)	0.0200 (5)	0.0060 (4)	0.0026 (4)	−0.0015 (4)
C5	0.0182 (4)	0.0140 (4)	0.0212 (5)	0.0065 (3)	0.0100 (4)	0.0069 (3)
C6	0.0156 (4)	0.0153 (4)	0.0189 (4)	0.0066 (3)	0.0072 (3)	0.0074 (4)
C7	0.0198 (4)	0.0179 (4)	0.0248 (5)	0.0106 (4)	0.0088 (4)	0.0110 (4)
C8	0.0203 (5)	0.0228 (5)	0.0225 (5)	0.0120 (4)	0.0054 (4)	0.0111 (4)
C9	0.0197 (4)	0.0209 (5)	0.0152 (4)	0.0104 (4)	0.0029 (3)	0.0072 (3)
C10	0.0350 (6)	0.0347 (6)	0.0284 (5)	0.0224 (5)	0.0167 (5)	0.0173 (5)
C11	0.0208 (5)	0.0225 (5)	0.0265 (5)	0.0087 (4)	0.0005 (4)	0.0058 (4)
C12	0.0139 (4)	0.0146 (4)	0.0164 (4)	0.0051 (3)	0.0050 (3)	0.0048 (3)
C13	0.0142 (4)	0.0148 (4)	0.0158 (4)	0.0061 (3)	0.0053 (3)	0.0054 (3)
C14	0.0160 (4)	0.0161 (4)	0.0162 (4)	0.0069 (3)	0.0045 (3)	0.0035 (3)
C15	0.0172 (4)	0.0164 (4)	0.0199 (4)	0.0081 (3)	0.0057 (3)	0.0058 (3)
C16	0.0182 (4)	0.0168 (4)	0.0175 (4)	0.0072 (3)	0.0050 (3)	0.0071 (3)
C17	0.0223 (5)	0.0264 (5)	0.0240 (5)	0.0078 (4)	0.0108 (4)	0.0103 (4)
C18	0.0218 (5)	0.0255 (5)	0.0201 (5)	0.0098 (4)	0.0023 (4)	0.0094 (4)
O1	0.0179 (3)	0.0168 (3)	0.0161 (3)	0.0064 (3)	0.0022 (3)	0.0048 (3)
O2	0.0313 (4)	0.0160 (3)	0.0258 (4)	0.0065 (3)	0.0112 (3)	0.0023 (3)
O3	0.0300 (4)	0.0151 (3)	0.0251 (4)	0.0111 (3)	0.0101 (3)	0.0059 (3)
O4	0.0261 (4)	0.0184 (3)	0.0152 (3)	0.0121 (3)	−0.0017 (3)	0.0023 (3)

C1—O1	1.3590 (11)	C10—H10B	0.96
C1—C13	1.3984 (13)	C10—H10C	0.96
C1—C2	1.4180 (13)	C11—H11A	0.96
C2—C5	1.4281 (13)	C11—H11B	0.96
C2—C3	1.4640 (13)	C11—H11C	0.96
C3—O2	1.2485 (12)	C12—O4	1.3543 (11)
C3—C4	1.5042 (14)	C12—C13	1.4048 (12)
C4—H4A	0.96	C13—C14	1.4590 (12)
C4—H4B	0.96	C14—C15	1.3332 (13)
C4—H4C	0.96	C14—H14	0.93
C5—O3	1.3439 (11)	C15—C16	1.5065 (13)
C5—C6	1.3986 (13)	C15—H15	0.93
C6—C12	1.3935 (12)	C16—O1	1.4711 (11)
C6—C7	1.4577 (13)	C16—C18	1.5232 (13)
C7—C8	1.3282 (14)	C16—C17	1.5281 (13)
C7—H7	0.93	C17—H17A	0.96
C8—C9	1.5038 (13)	C17—H17B	0.96
C8—H8	0.93	C17—H17C	0.96
C9—O4	1.4749 (11)	C18—H18A	0.96
C9—C11	1.5228 (14)	C18—H18B	0.96
C9—C10	1.5238 (14)	C18—H18C	0.96
C10—H10A	0.96	O3—H3	0.82
O1—C1—C13	119.17 (8)	C9—C11—H11A	109.5
O1—C1—C2	118.15 (8)	C9—C11—H11B	109.5
C13—C1—C2	122.58 (8)	H11A—C11—H11B	109.5
C1—C2—C5	116.61 (8)	C9—C11—H11C	109.5
C1—C2—C3	124.92 (9)	H11A—C11—H11C	109.5
C5—C2—C3	118.47 (9)	H11B—C11—H11C	109.5
O2—C3—C2	120.10 (9)	O4—C12—C6	122.09 (8)
O2—C3—C4	117.13 (9)	O4—C12—C13	115.82 (8)
C2—C3—C4	122.76 (9)	C6—C12—C13	122.09 (8)
C3—C4—H4A	109.5	C1—C13—C12	118.05 (8)
C3—C4—H4B	109.5	C1—C13—C14	118.47 (8)
H4A—C4—H4B	109.5	C12—C13—C14	123.36 (8)
C3—C4—H4C	109.5	C15—C14—C13	119.82 (8)
H4A—C4—H4C	109.5	C15—C14—H14	120.1
H4B—C4—H4C	109.5	C13—C14—H14	120.1
O3—C5—C6	116.62 (9)	C14—C15—C16	119.64 (8)
O3—C5—C2	121.48 (9)	C14—C15—H15	120.2
C6—C5—C2	121.89 (9)	C16—C15—H15	120.2
C12—C6—C5	118.72 (8)	O1—C16—C15	109.49 (7)
C12—C6—C7	118.82 (8)	O1—C16—C18	104.23 (7)
C5—C6—C7	122.46 (9)	C15—C16—C18	112.21 (8)
C8—C7—C6	120.13 (9)	O1—C16—C17	108.08 (8)
C8—C7—H7	119.9	C15—C16—C17	111.13 (8)
C6—C7—H7	119.9	C18—C16—C17	111.38 (8)
C7—C8—C9	123.48 (9)	C16—C17—H17A	109.5
C7—C8—H8	118.3	C16—C17—H17B	109.5
C9—C8—H8	118.3	H17A—C17—H17B	109.5
O4—C9—C8	112.70 (8)	C16—C17—H17C	109.5
O4—C9—C11	104.96 (8)	H17A—C17—H17C	109.5
C8—C9—C11	111.35 (8)	H17B—C17—H17C	109.5
O4—C9—C10	106.15 (8)	C16—C18—H18A	109.5
C8—C9—C10	110.78 (8)	C16—C18—H18B	109.5
C11—C9—C10	110.66 (9)	H18A—C18—H18B	109.5
C9—C10—H10A	109.5	C16—C18—H18C	109.5
C9—C10—H10B	109.5	H18A—C18—H18C	109.5
H10A—C10—H10B	109.5	H18B—C18—H18C	109.5
C9—C10—H10C	109.5	C1—O1—C16	117.84 (7)
H10A—C10—H10C	109.5	C5—O3—H3	109.5
H10B—C10—H10C	109.5	C12—O4—C9	122.57 (7)
O1—C1—C2—C5	−177.70 (8)	C7—C6—C12—C13	178.75 (8)
C13—C1—C2—C5	−1.41 (14)	O1—C1—C13—C12	178.20 (8)
O1—C1—C2—C3	2.90 (14)	C2—C1—C13—C12	1.95 (14)
C13—C1—C2—C3	179.19 (8)	O1—C1—C13—C14	2.07 (13)
C1—C2—C3—O2	−177.92 (9)	C2—C1—C13—C14	−174.19 (8)
C5—C2—C3—O2	2.69 (14)	O4—C12—C13—C1	179.79 (8)
C1—C2—C3—C4	2.05 (15)	C6—C12—C13—C1	−0.41 (14)
C5—C2—C3—C4	−177.34 (8)	O4—C12—C13—C14	−4.28 (13)
C1—C2—C5—O3	179.80 (8)	C6—C12—C13—C14	175.53 (8)
C3—C2—C5—O3	−0.76 (14)	C1—C13—C14—C15	−15.41 (13)
C1—C2—C5—C6	−0.67 (14)	C12—C13—C14—C15	168.67 (9)
C3—C2—C5—C6	178.77 (8)	C13—C14—C15—C16	−3.69 (13)
O3—C5—C6—C12	−178.33 (8)	C14—C15—C16—O1	32.30 (12)
C2—C5—C6—C12	2.12 (14)	C14—C15—C16—C18	147.53 (9)
O3—C5—C6—C7	1.33 (14)	C14—C15—C16—C17	−87.03 (11)
C2—C5—C6—C7	−178.22 (8)	C13—C1—O1—C16	29.94 (12)
C12—C6—C7—C8	1.98 (14)	C2—C1—O1—C16	−153.63 (8)
C5—C6—C7—C8	−177.68 (9)	C15—C16—O1—C1	−45.75 (10)
C6—C7—C8—C9	1.28 (16)	C18—C16—O1—C1	−165.98 (8)
C7—C8—C9—O4	−4.60 (14)	C17—C16—O1—C1	75.44 (10)
C7—C8—C9—C11	−122.24 (11)	C6—C12—O4—C9	−2.36 (14)
C7—C8—C9—C10	114.16 (11)	C13—C12—O4—C9	177.44 (8)
C5—C6—C12—O4	178.22 (8)	C8—C9—O4—C12	5.12 (13)
C7—C6—C12—O4	−1.45 (14)	C11—C9—O4—C12	126.46 (9)
C5—C6—C12—C13	−1.58 (14)	C10—C9—O4—C12	−116.31 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.76	2.4897 (11)	148
C11—H11A···O2i	0.96	2.48	3.3829 (14)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.76	2.4897 (11)	148
C11—H11A⋯O2i	0.96	2.48	3.3829 (14)	156

Symmetry code: (i) .