1-Hydr-oxy-3-(3-methyl-but-2-en-yloxy)xanthone.

In the title compound, C(18)H(16)O(4), a monoprenylated xanthone, the xanthone skeleton exhibits an essentially planar conformation (r.m.s. deviation 0.0072 Å) and the isoprenyl side chain remains approximately in the mean plane of the xanthone unit, making a dihedral angle of 4.5 (2)°. The hydroxyl group forms an intra-molecular O-H⋯O hydrogen bond. Moreover, there is a weak inter-molecular C-H⋯O inter-action between a ring C atom and the xanthene O atom. In the crystal structure, there are no inter-molecular hydrogen bonds and the crystallographic packing is governed by van der Waals forces, leading to an arrangement in which the mol-ecules assemble with their planes parallel to each other, having a separation of 3.6 (3) Å.

Related literature

For a review of the biological activity of prenylated xanthones, see: Pinto et al. (2005 ▶). For background literature and synthesis of prenylated xanthones, see: Pinto et al. (2005 ▶); Epifano et al. (2007 ▶); Castanheiro et al. (2007 ▶). For the synthesis of the title compound using microwave radiation, see: Castanheiro et al. (2009 ▶). For analysis of related structures of xanthone derivatives, see: Gales et al. (2001 ▶, 2005 ▶ a,b); Castanheiro et al. (2007 ▶). For the interaction with biological membranes and target proteins, see: Maia et al. (2005 ▶); Epifano et al. (2007 ▶). For a review of prenylated xanthone crystal structures, see: Gales & Damas, 2005 ▶).

Experimental

Crystal data

C18H16O4

M = 296.31

Triclinic,

a = 4.8199 (3) Å

b = 11.7014 (8) Å

c = 13.6176 (10) Å

α = 77.329 (6)°

β = 88.582 (6)°

γ = 79.039 (6)°

V = 735.54 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.4 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Gemini PX Ultra CCD area-detector diffractometer

Absorption correction: none

8520 measured reflections

2981 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.147

S = 1.07

2981 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Johnson & Burnett, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040069/bv2126sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040069/bv2126Isup2.hkl

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

C18H16O4	Z = 2
Mr = 296.31	F(000) = 312
Triclinic, P1	Dx = 1.338 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8199 (3) Å	Cell parameters from 1141 reflections
b = 11.7014 (8) Å	θ = 4.0–24.3°
c = 13.6176 (10) Å	µ = 0.09 mm−1
α = 77.329 (6)°	T = 295 K
β = 88.582 (6)°	Plate, yellow
γ = 79.039 (6)°	0.4 × 0.2 × 0.1 mm
V = 735.54 (9) Å3

Oxford Diffraction Gemini PX Ultra CCD area-detector diffractometer	1958 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 26.4°, θmin = 2.6°
ω and θ scans	h = −5→6
8520 measured reflections	k = −14→14
2981 independent reflections	l = −17→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0771P)2 + 0.0559P] where P = (Fo2 + 2Fc2)/3
2981 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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	0.2991 (3)	0.54781 (11)	0.38058 (10)	0.0702 (4)
H1A	0.4106	0.5456	0.3343	0.105*
O2	0.0013 (3)	0.78593 (11)	0.61948 (9)	0.0652 (4)
O10	0.6160 (2)	0.91544 (10)	0.36924 (8)	0.0558 (3)
O11	0.6489 (3)	0.62252 (12)	0.24577 (10)	0.0734 (4)
C1	0.3046 (3)	0.64516 (14)	0.41726 (13)	0.0525 (4)
C2	0.1471 (3)	0.66156 (14)	0.50003 (12)	0.0538 (4)
H2A	0.0408	0.6055	0.5307	0.065*
C3	0.1479 (3)	0.76265 (15)	0.53766 (12)	0.0518 (4)
C4	0.3038 (3)	0.84872 (15)	0.49224 (12)	0.0538 (4)
H4A	0.3000	0.9171	0.5168	0.065*
C4A	0.4623 (3)	0.82954 (14)	0.41054 (11)	0.0480 (4)
C5	0.9287 (4)	0.99283 (16)	0.25015 (13)	0.0612 (5)
H5A	0.9186	1.0567	0.2813	0.073*
C6	1.0918 (4)	0.98563 (18)	0.16677 (14)	0.0689 (5)
H6A	1.1906	1.0462	0.1408	0.083*
C7	1.1124 (4)	0.89031 (18)	0.12043 (14)	0.0694 (5)
H7A	1.2247	0.8870	0.0642	0.083*
C8	0.9666 (4)	0.80095 (17)	0.15780 (13)	0.0634 (5)
H8A	0.9809	0.7367	0.1269	0.076*
C8A	0.7966 (3)	0.80542 (15)	0.24201 (12)	0.0520 (4)
C9	0.6388 (3)	0.71111 (15)	0.28351 (13)	0.0546 (4)
C9A	0.4708 (3)	0.72862 (14)	0.36983 (12)	0.0487 (4)
C10A	0.7792 (3)	0.90220 (15)	0.28679 (12)	0.0516 (4)
C1X	−0.1460 (4)	0.69521 (16)	0.67349 (13)	0.0652 (5)
H1XA	−0.0128	0.6219	0.6991	0.078*
H1XB	−0.2807	0.6790	0.6290	0.078*
C2X	−0.2946 (4)	0.74034 (17)	0.75770 (14)	0.0716 (5)
H2XA	−0.3558	0.8224	0.7476	0.086*
C3X	−0.3486 (4)	0.67573 (16)	0.84547 (13)	0.0642 (5)
C4AX	−0.5155 (5)	0.7288 (2)	0.92405 (18)	0.0985 (8)
H4AA	−0.5531	0.8142	0.9028	0.148*
H4AB	−0.4096	0.7055	0.9863	0.148*
H4AC	−0.6910	0.7007	0.9334	0.148*
C4BX	−0.2550 (6)	0.5424 (2)	0.87218 (17)	0.1053 (8)
H4BA	−0.1111	0.5186	0.8268	0.158*
H4BB	−0.4135	0.5052	0.8669	0.158*
H4BC	−0.1808	0.5184	0.9399	0.158*

	U11	U22	U33	U12	U13	U23
O1	0.0865 (9)	0.0539 (7)	0.0832 (9)	−0.0265 (6)	0.0115 (7)	−0.0323 (6)
O2	0.0812 (8)	0.0638 (8)	0.0629 (7)	−0.0349 (6)	0.0260 (6)	−0.0248 (6)
O10	0.0642 (7)	0.0533 (7)	0.0592 (7)	−0.0242 (5)	0.0179 (5)	−0.0229 (5)
O11	0.0800 (8)	0.0676 (8)	0.0872 (9)	−0.0196 (7)	0.0159 (7)	−0.0447 (7)
C1	0.0567 (9)	0.0432 (9)	0.0611 (10)	−0.0120 (7)	−0.0055 (8)	−0.0158 (7)
C2	0.0588 (10)	0.0490 (10)	0.0579 (10)	−0.0207 (8)	0.0024 (8)	−0.0118 (8)
C3	0.0562 (9)	0.0508 (10)	0.0519 (9)	−0.0157 (7)	0.0032 (7)	−0.0145 (7)
C4	0.0635 (10)	0.0489 (9)	0.0579 (9)	−0.0211 (8)	0.0108 (8)	−0.0229 (8)
C4A	0.0511 (9)	0.0435 (9)	0.0530 (9)	−0.0138 (7)	0.0024 (7)	−0.0140 (7)
C5	0.0684 (11)	0.0575 (10)	0.0618 (10)	−0.0196 (9)	0.0132 (8)	−0.0161 (8)
C6	0.0727 (12)	0.0681 (12)	0.0644 (11)	−0.0201 (10)	0.0158 (9)	−0.0071 (9)
C7	0.0728 (12)	0.0791 (14)	0.0542 (10)	−0.0099 (10)	0.0166 (9)	−0.0157 (9)
C8	0.0668 (11)	0.0676 (12)	0.0573 (10)	−0.0061 (9)	0.0053 (9)	−0.0229 (9)
C8A	0.0504 (9)	0.0562 (10)	0.0503 (9)	−0.0056 (7)	0.0025 (7)	−0.0174 (8)
C9	0.0542 (9)	0.0522 (10)	0.0617 (10)	−0.0063 (7)	−0.0029 (8)	−0.0241 (8)
C9A	0.0476 (8)	0.0463 (9)	0.0545 (9)	−0.0088 (7)	−0.0027 (7)	−0.0160 (7)
C10A	0.0525 (9)	0.0540 (10)	0.0492 (9)	−0.0100 (7)	0.0050 (7)	−0.0140 (7)
C1X	0.0767 (12)	0.0563 (11)	0.0664 (11)	−0.0262 (9)	0.0178 (9)	−0.0117 (9)
C2X	0.0800 (13)	0.0569 (11)	0.0794 (13)	−0.0187 (9)	0.0279 (10)	−0.0161 (10)
C3X	0.0750 (12)	0.0612 (11)	0.0605 (10)	−0.0236 (9)	0.0129 (9)	−0.0141 (9)
C4AX	0.1244 (19)	0.0849 (16)	0.0881 (15)	−0.0254 (14)	0.0440 (14)	−0.0225 (13)
C4BX	0.163 (2)	0.0746 (15)	0.0736 (14)	−0.0225 (15)	0.0266 (15)	−0.0095 (11)

O1—C1	1.3453 (19)	C7—C8	1.369 (3)
O1—H1A	0.8200	C7—H7A	0.9300
O2—C3	1.3548 (19)	C8—C8A	1.397 (2)
O2—C1X	1.4460 (18)	C8—H8A	0.9300
O10—C10A	1.3744 (19)	C8A—C10A	1.388 (2)
O10—C4A	1.3748 (18)	C8A—C9	1.463 (2)
O11—C9	1.247 (2)	C9—C9A	1.440 (2)
C1—C2	1.371 (2)	C1X—C2X	1.479 (3)
C1—C9A	1.417 (2)	C1X—H1XA	0.9700
C2—C3	1.389 (2)	C1X—H1XB	0.9700
C2—H2A	0.9300	C2X—C3X	1.316 (2)
C3—C4	1.398 (2)	C2X—H2XA	0.9300
C4—C4A	1.369 (2)	C3X—C4AX	1.495 (3)
C4—H4A	0.9300	C3X—C4BX	1.504 (3)
C4A—C9A	1.404 (2)	C4AX—H4AA	0.9600
C5—C6	1.374 (2)	C4AX—H4AB	0.9600
C5—C10A	1.391 (2)	C4AX—H4AC	0.9600
C5—H5A	0.9300	C4BX—H4BA	0.9600
C6—C7	1.384 (3)	C4BX—H4BB	0.9600
C6—H6A	0.9300	C4BX—H4BC	0.9600
C1—O1—H1A	109.5	O11—C9—C9A	122.80 (16)
C3—O2—C1X	117.02 (13)	O11—C9—C8A	121.86 (16)
C10A—O10—C4A	119.38 (13)	C9A—C9—C8A	115.34 (15)
O1—C1—C2	118.92 (15)	C4A—C9A—C1	116.83 (15)
O1—C1—C9A	119.70 (15)	C4A—C9A—C9	121.62 (14)
C2—C1—C9A	121.37 (15)	C1—C9A—C9	121.55 (15)
C1—C2—C3	119.42 (15)	O10—C10A—C8A	123.03 (15)
C1—C2—H2A	120.3	O10—C10A—C5	115.61 (15)
C3—C2—H2A	120.3	C8A—C10A—C5	121.36 (15)
O2—C3—C2	123.65 (14)	O2—C1X—C2X	107.68 (14)
O2—C3—C4	115.03 (14)	O2—C1X—H1XA	110.2
C2—C3—C4	121.31 (15)	C2X—C1X—H1XA	110.2
C4A—C4—C3	118.15 (15)	O2—C1X—H1XB	110.2
C4A—C4—H4A	120.9	C2X—C1X—H1XB	110.2
C3—C4—H4A	120.9	H1XA—C1X—H1XB	108.5
C4—C4A—O10	116.23 (14)	C3X—C2X—C1X	126.38 (18)
C4—C4A—C9A	122.89 (14)	C3X—C2X—H2XA	116.8
O10—C4A—C9A	120.88 (14)	C1X—C2X—H2XA	116.8
C6—C5—C10A	118.31 (18)	C2X—C3X—C4AX	122.55 (19)
C6—C5—H5A	120.8	C2X—C3X—C4BX	122.09 (19)
C10A—C5—H5A	120.8	C4AX—C3X—C4BX	115.33 (16)
C5—C6—C7	121.54 (18)	C3X—C4AX—H4AA	109.5
C5—C6—H6A	119.2	C3X—C4AX—H4AB	109.5
C7—C6—H6A	119.2	H4AA—C4AX—H4AB	109.5
C8—C7—C6	119.64 (17)	C3X—C4AX—H4AC	109.5
C8—C7—H7A	120.2	H4AA—C4AX—H4AC	109.5
C6—C7—H7A	120.2	H4AB—C4AX—H4AC	109.5
C7—C8—C8A	120.57 (17)	C3X—C4BX—H4BA	109.5
C7—C8—H8A	119.7	C3X—C4BX—H4BB	109.5
C8A—C8—H8A	119.7	H4BA—C4BX—H4BB	109.5
C10A—C8A—C8	118.56 (16)	C3X—C4BX—H4BC	109.5
C10A—C8A—C9	119.75 (15)	H4BA—C4BX—H4BC	109.5
C8—C8A—C9	121.69 (16)	H4BB—C4BX—H4BC	109.5
O1—C1—C2—C3	−179.05 (15)	C4—C4A—C9A—C9	179.75 (14)
C9A—C1—C2—C3	0.7 (2)	O10—C4A—C9A—C9	−0.2 (2)
C1X—O2—C3—C2	4.5 (2)	O1—C1—C9A—C4A	178.64 (14)
C1X—O2—C3—C4	−175.47 (14)	C2—C1—C9A—C4A	−1.1 (2)
C1—C2—C3—O2	−179.37 (14)	O1—C1—C9A—C9	−0.9 (2)
C1—C2—C3—C4	0.6 (2)	C2—C1—C9A—C9	179.34 (14)
O2—C3—C4—C4A	178.50 (13)	O11—C9—C9A—C4A	−179.71 (15)
C2—C3—C4—C4A	−1.5 (2)	C8A—C9—C9A—C4A	−0.2 (2)
C3—C4—C4A—O10	−178.95 (13)	O11—C9—C9A—C1	−0.2 (2)
C3—C4—C4A—C9A	1.1 (2)	C8A—C9—C9A—C1	179.34 (13)
C10A—O10—C4A—C4	−179.75 (12)	C4A—O10—C10A—C8A	0.2 (2)
C10A—O10—C4A—C9A	0.2 (2)	C4A—O10—C10A—C5	−179.70 (13)
C10A—C5—C6—C7	−1.0 (3)	C8—C8A—C10A—O10	179.40 (14)
C5—C6—C7—C8	0.3 (3)	C9—C8A—C10A—O10	−0.7 (2)
C6—C7—C8—C8A	0.2 (3)	C8—C8A—C10A—C5	−0.7 (2)
C7—C8—C8A—C10A	−0.1 (2)	C9—C8A—C10A—C5	179.25 (15)
C7—C8—C8A—C9	−179.96 (15)	C6—C5—C10A—O10	−178.90 (14)
C10A—C8A—C9—O11	−179.85 (15)	C6—C5—C10A—C8A	1.2 (3)
C8—C8A—C9—O11	0.1 (3)	C3—O2—C1X—C2X	−178.84 (14)
C10A—C8A—C9—C9A	0.6 (2)	O2—C1X—C2X—C3X	−149.12 (19)
C8—C8A—C9—C9A	−179.45 (13)	C1X—C2X—C3X—C4AX	−176.29 (19)
C4—C4A—C9A—C1	0.2 (2)	C1X—C2X—C3X—C4BX	1.5 (3)
O10—C4A—C9A—C1	−179.79 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O11	0.82	1.85	2.5846 (17)	148
C5—H5A···O2i	0.93	2.60	3.514 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O11	0.82	1.85	2.5846 (17)	148
C5—H5A⋯O2i	0.93	2.60	3.514 (2)	168

Symmetry code: (i) .