7-Hy-droxy-6-meth-oxy-2H-chromen-2-one.

The title compound, C(10)H(8)O(4), is one of the coumarins existing in Morinda citrifolia L (Noni). The chromenone ring system is approximately planar with a maximum deviation of 0.0208 (14) Å. The meth-oxy group does not deviate from this plane [C-O-C-C torsion angle = -1.5 (3)°], indicating that the whole mol-ecule is almost planar. In the crystal packing, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains. These are further connected by C-H⋯O hydrogen bonds.

Related literature

For background and the biological activity of Morinda citrifolia L, see: Wang et al. (2002 ▶); Samoylenko et al. (2006 ▶); Silva et al. (2001 ▶); Goy et al. (1993 ▶); Cassady et al. (1979 ▶); Shaw et al. (2003 ▶); Ding et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H8O4

M = 192.16

Orthorhombic,

a = 7.0771 (2) Å

b = 17.3485 (4) Å

c = 6.9672 (2) Å

V = 855.41 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.39 × 0.11 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.956, T max = 0.991

9630 measured reflections

1364 independent reflections

1213 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.07

1364 reflections

132 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029296/bt5305sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029296/bt5305Isup2.hkl

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

C10H8O4	F(000) = 400
Mr = 192.16	Dx = 1.492 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3125 reflections
a = 7.0771 (2) Å	θ = 2.4–29.9°
b = 17.3485 (4) Å	µ = 0.12 mm−1
c = 6.9672 (2) Å	T = 100 K
V = 855.41 (4) Å3	Needle, yellow
Z = 4	0.39 × 0.11 × 0.08 mm

Bruker SMART APEXII CCD area-detector diffractometer	1364 independent reflections
Radiation source: fine-focus sealed tube	1213 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 30.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→9
Tmin = 0.956, Tmax = 0.991	k = −24→24
9630 measured reflections	l = −9→8

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1813P] where P = (Fo2 + 2Fc2)/3
1364 reflections	(Δ/σ)max = 0.001
132 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.82231 (19)	0.37644 (6)	0.5023 (2)	0.0161 (3)
O2	0.8589 (2)	0.49194 (7)	0.3781 (2)	0.0221 (3)
O3	0.7202 (2)	0.13880 (7)	0.8064 (2)	0.0223 (3)
O4	0.81670 (19)	0.05917 (7)	0.4922 (2)	0.0199 (3)
C1	0.7724 (3)	0.17732 (9)	0.6463 (3)	0.0153 (3)
C2	0.7725 (3)	0.25710 (9)	0.6524 (3)	0.0147 (3)
H2A	0.7382	0.2832	0.7636	0.018*
C3	0.8251 (2)	0.29720 (9)	0.4884 (3)	0.0144 (3)
C4	0.8665 (2)	0.42295 (9)	0.3488 (3)	0.0171 (4)
C5	0.9176 (3)	0.38545 (10)	0.1709 (3)	0.0182 (4)
H5A	0.9461	0.4152	0.0637	0.022*
C6	0.9243 (2)	0.30757 (10)	0.1584 (3)	0.0171 (3)
H6A	0.9606	0.2846	0.0437	0.021*
C7	0.8762 (3)	0.26016 (9)	0.3195 (3)	0.0145 (3)
C8	0.8758 (2)	0.17879 (9)	0.3153 (3)	0.0151 (3)
H8A	0.9099	0.1529	0.2037	0.018*
C9	0.8248 (3)	0.13773 (9)	0.4770 (3)	0.0148 (3)
C10	0.8609 (3)	0.01496 (9)	0.3244 (3)	0.0218 (4)
H10A	0.8482	−0.0389	0.3527	0.033*
H10B	0.9884	0.0256	0.2854	0.033*
H10C	0.7758	0.0286	0.2226	0.033*
H1O3	0.712 (4)	0.0869 (16)	0.782 (5)	0.048 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0216 (6)	0.0117 (5)	0.0150 (6)	−0.0002 (4)	−0.0009 (6)	0.0010 (5)
O2	0.0300 (7)	0.0133 (5)	0.0230 (8)	−0.0011 (5)	−0.0046 (6)	0.0033 (5)
O3	0.0378 (8)	0.0135 (5)	0.0157 (7)	−0.0024 (5)	0.0077 (7)	0.0012 (6)
O4	0.0300 (7)	0.0116 (5)	0.0182 (7)	−0.0008 (5)	0.0038 (6)	−0.0021 (6)
C1	0.0174 (8)	0.0150 (7)	0.0135 (9)	−0.0022 (6)	−0.0016 (8)	0.0022 (7)
C2	0.0175 (8)	0.0149 (7)	0.0117 (8)	−0.0005 (6)	0.0008 (8)	−0.0013 (7)
C3	0.0153 (7)	0.0117 (6)	0.0162 (9)	−0.0009 (6)	−0.0027 (7)	0.0029 (8)
C4	0.0170 (8)	0.0158 (7)	0.0185 (10)	−0.0023 (6)	−0.0039 (7)	0.0064 (7)
C5	0.0196 (8)	0.0193 (7)	0.0156 (9)	−0.0019 (6)	−0.0017 (8)	0.0056 (7)
C6	0.0166 (8)	0.0199 (7)	0.0149 (8)	−0.0002 (6)	−0.0007 (8)	0.0022 (7)
C7	0.0147 (8)	0.0150 (7)	0.0138 (9)	0.0003 (6)	−0.0015 (8)	0.0006 (7)
C8	0.0170 (8)	0.0150 (7)	0.0134 (8)	−0.0005 (6)	0.0006 (8)	−0.0010 (7)
C9	0.0158 (8)	0.0112 (6)	0.0173 (9)	−0.0001 (6)	−0.0010 (7)	−0.0008 (7)
C10	0.0284 (9)	0.0148 (7)	0.0223 (10)	0.0015 (6)	0.0034 (9)	−0.0064 (8)

O1—C4	1.376 (2)	C4—C5	1.446 (3)
O1—C3	1.3781 (18)	C5—C6	1.355 (2)
O2—C4	1.215 (2)	C5—H5A	0.9300
O3—C1	1.352 (2)	C6—C7	1.432 (2)
O3—H1O3	0.92 (3)	C6—H6A	0.9300
O4—C9	1.3682 (18)	C7—C8	1.412 (2)
O4—C10	1.433 (2)	C8—C9	1.381 (3)
C1—C2	1.385 (2)	C8—H8A	0.9300
C1—C9	1.415 (3)	C10—H10A	0.9600
C2—C3	1.388 (3)	C10—H10B	0.9600
C2—H2A	0.9300	C10—H10C	0.9600
C3—C7	1.389 (3)
C4—O1—C3	121.82 (16)	C5—C6—C7	120.94 (18)
C1—O3—H1O3	111 (2)	C5—C6—H6A	119.5
C9—O4—C10	117.42 (16)	C7—C6—H6A	119.5
O3—C1—C2	117.99 (16)	C3—C7—C8	118.68 (16)
O3—C1—C9	121.33 (15)	C3—C7—C6	117.39 (14)
C2—C1—C9	120.68 (16)	C8—C7—C6	123.93 (17)
C1—C2—C3	118.44 (16)	C9—C8—C7	119.95 (16)
C1—C2—H2A	120.8	C9—C8—H8A	120.0
C3—C2—H2A	120.8	C7—C8—H8A	120.0
O1—C3—C2	116.00 (17)	O4—C9—C8	126.04 (17)
O1—C3—C7	121.65 (16)	O4—C9—C1	114.05 (17)
C2—C3—C7	122.35 (14)	C8—C9—C1	119.90 (14)
O2—C4—O1	115.91 (18)	O4—C10—H10A	109.5
O2—C4—C5	126.75 (17)	O4—C10—H10B	109.5
O1—C4—C5	117.34 (14)	H10A—C10—H10B	109.5
C6—C5—C4	120.84 (17)	O4—C10—H10C	109.5
C6—C5—H5A	119.6	H10A—C10—H10C	109.5
C4—C5—H5A	119.6	H10B—C10—H10C	109.5
O3—C1—C2—C3	−179.72 (16)	C2—C3—C7—C6	178.81 (16)
C9—C1—C2—C3	0.1 (3)	C5—C6—C7—C3	−0.8 (3)
C4—O1—C3—C2	−178.29 (15)	C5—C6—C7—C8	178.45 (16)
C4—O1—C3—C7	1.2 (2)	C3—C7—C8—C9	0.2 (2)
C1—C2—C3—O1	179.84 (14)	C6—C7—C8—C9	−179.06 (17)
C1—C2—C3—C7	0.3 (3)	C10—O4—C9—C8	−1.5 (3)
C3—O1—C4—O2	179.90 (15)	C10—O4—C9—C1	177.71 (15)
C3—O1—C4—C5	−0.3 (2)	C7—C8—C9—O4	179.38 (15)
O2—C4—C5—C6	178.64 (18)	C7—C8—C9—C1	0.2 (3)
O1—C4—C5—C6	−1.1 (3)	O3—C1—C9—O4	0.2 (3)
C4—C5—C6—C7	1.7 (3)	C2—C1—C9—O4	−179.60 (15)
O1—C3—C7—C8	−179.93 (14)	O3—C1—C9—C8	179.42 (15)
C2—C3—C7—C8	−0.5 (3)	C2—C1—C9—C8	−0.4 (3)
O1—C3—C7—C6	−0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O2i	0.92 (3)	1.85 (3)	2.6558 (17)	146 (3)
C5—H5A···O2ii	0.93	2.48	3.345 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O2i	0.92 (3)	1.85 (3)	2.6558 (17)	146 (3)
C5—H5A⋯O2ii	0.93	2.48	3.345 (2)	154

Symmetry codes: (i) ; (ii) .