2-(2,6-Dimethoxy-phen-yl)-5-hydr-oxy-7-meth-oxy-4H-1-benzopyran-4-one.

In the title compound, C(18)H(16)O(6), the dimethoxy-phenyl ring is rotated by 61.8 (1)° from the plane of the benzopyran system. The mol-ecule is stabilized by an intra-molecular O-H⋯O hydrogen bond.

Related literature

The title compound, along with a terpinoid and six other flavonoids, was isolated from the roots and the aerial parts of Andrographis peniculata Nees (Reddy et al., 2003 ▶), a herb widely distributed in the plains of India and Sri Lanka (Gamble, 1956 ▶). In traditional Indian medicine, the whole plant of A. peniculata is extensively used in the treatment of dyspepsia, dysentery, malaria, respiratory infections and as an anti­dote for snake bites, see: Kirtikar & Basu (1975 ▶); Chopra et al. (1980 ▶).

Experimental

Crystal data

C18H16O6

M = 328.31

Monoclinic,

a = 11.003 (7) Å

b = 11.015 (7) Å

c = 13.734 (9) Å

β = 113.159 (10)°

V = 1530.4 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.69 × 0.37 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.929, T max = 0.969

7431 measured reflections

2675 independent reflections

2300 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.04

2675 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032383/hg2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032383/hg2533Isup2.hkl

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

C18H16O6	F(000) = 688
Mr = 328.31	Dx = 1.425 Mg m−3Dm = 1.42 Mg m−3Dm measured by none
Monoclinic, P21/n	Melting point: 469 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.003 (7) Å	Cell parameters from 25 reflections
b = 11.015 (7) Å	θ = 2–25°
c = 13.734 (9) Å	µ = 0.11 mm−1
β = 113.159 (10)°	T = 295 K
V = 1530.4 (17) Å3	Needle, colourless
Z = 4	0.69 × 0.37 × 0.36 mm

Bruker SMART CCD area-detector diffractometer	2675 independent reflections
Radiation source: fine-focus sealed tube	2300 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 2.5°
ω scans	h = −7→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −13→13
Tmin = 0.929, Tmax = 0.969	l = −16→16
7431 measured 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.3516P] where P = (Fo2 + 2Fc2)/3
2675 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 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 ?t 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	0.95634 (9)	0.63933 (8)	0.16154 (8)	0.0376 (3)
C2	0.97394 (14)	0.75775 (13)	0.14376 (12)	0.0361 (3)
C3	1.06401 (15)	0.79404 (13)	0.10773 (12)	0.0412 (4)
H3	1.0720	0.8764	0.0967	0.049*
C4	1.14884 (15)	0.71009 (13)	0.08555 (12)	0.0391 (3)
O4	1.23188 (12)	0.74190 (10)	0.04933 (10)	0.0526 (3)
C5	1.13251 (14)	0.58600 (13)	0.10870 (11)	0.0350 (3)
C6	1.21312 (15)	0.49245 (14)	0.09621 (12)	0.0393 (3)
O6	1.30566 (12)	0.52024 (11)	0.05872 (11)	0.0560 (3)
H6	1.3026	0.5931	0.0458	0.084*
C7	1.19766 (16)	0.37579 (14)	0.12164 (12)	0.0436 (4)
H7	1.2524	0.3151	0.1146	0.052*
C8	1.09978 (15)	0.34760 (13)	0.15815 (12)	0.0403 (3)
O8	1.09338 (12)	0.22951 (9)	0.18118 (10)	0.0537 (3)
C9	1.01709 (14)	0.43571 (13)	0.16945 (11)	0.0375 (3)
H9	0.9506	0.4162	0.1926	0.045*
C5A	1.03645 (13)	0.55351 (13)	0.14532 (11)	0.0333 (3)
C10	0.9930 (2)	0.19296 (17)	0.21541 (17)	0.0638 (5)
H10A	1.0044	0.2346	0.2798	0.096*
H10B	0.9987	0.1070	0.2278	0.096*
H10C	0.9080	0.2125	0.1618	0.096*
C1'	0.88314 (14)	0.83990 (13)	0.16728 (12)	0.0376 (3)
C2'	0.88837 (14)	0.85308 (13)	0.26936 (12)	0.0396 (4)
O2'	0.97735 (11)	0.78129 (10)	0.34356 (8)	0.0467 (3)
C3'	0.80767 (16)	0.93686 (15)	0.28990 (14)	0.0479 (4)
H3'	0.8119	0.9467	0.3584	0.057*
C4'	0.72169 (17)	1.00504 (15)	0.20869 (15)	0.0521 (4)
H4'	0.6680	1.0613	0.2231	0.063*
C5'	0.71262 (16)	0.99273 (14)	0.10730 (14)	0.0493 (4)
H5'	0.6523	1.0388	0.0530	0.059*
C6'	0.79435 (15)	0.91074 (14)	0.08648 (13)	0.0426 (4)
O6'	0.79624 (13)	0.89242 (11)	−0.00985 (9)	0.0594 (3)
C12	0.70572 (18)	0.95611 (16)	−0.09779 (14)	0.0551 (4)
H12A	0.6172	0.9317	−0.1097	0.083*
H12B	0.7232	0.9381	−0.1595	0.083*
H12C	0.7152	1.0418	−0.0840	0.083*
C11	0.99169 (19)	0.79582 (17)	0.44992 (13)	0.0557 (5)
H11A	1.0145	0.8785	0.4713	0.084*
H11B	1.0603	0.7430	0.4947	0.084*
H11C	0.9100	0.7757	0.4558	0.084*

	U11	U22	U33	U12	U13	U23
O1	0.0400 (6)	0.0327 (5)	0.0456 (6)	0.0029 (4)	0.0227 (5)	−0.0012 (4)
C2	0.0384 (8)	0.0313 (7)	0.0373 (8)	0.0008 (6)	0.0135 (6)	−0.0020 (6)
C3	0.0455 (9)	0.0317 (8)	0.0498 (9)	0.0011 (6)	0.0223 (7)	0.0006 (7)
C4	0.0404 (8)	0.0408 (8)	0.0390 (8)	−0.0015 (7)	0.0187 (7)	−0.0003 (7)
O4	0.0583 (7)	0.0444 (6)	0.0717 (8)	−0.0006 (5)	0.0435 (7)	0.0037 (6)
C5	0.0362 (7)	0.0364 (8)	0.0322 (7)	0.0005 (6)	0.0132 (6)	−0.0025 (6)
C6	0.0388 (8)	0.0418 (8)	0.0404 (8)	0.0018 (6)	0.0188 (7)	−0.0038 (7)
O6	0.0579 (7)	0.0495 (7)	0.0795 (8)	0.0053 (6)	0.0474 (7)	0.0004 (6)
C7	0.0447 (9)	0.0378 (8)	0.0496 (9)	0.0081 (7)	0.0200 (7)	−0.0040 (7)
C8	0.0442 (8)	0.0336 (8)	0.0394 (8)	0.0001 (7)	0.0127 (7)	−0.0025 (7)
O8	0.0639 (8)	0.0317 (6)	0.0708 (8)	0.0032 (5)	0.0323 (7)	0.0043 (5)
C9	0.0387 (8)	0.0360 (8)	0.0395 (8)	−0.0017 (6)	0.0172 (7)	−0.0011 (6)
C5A	0.0340 (7)	0.0334 (7)	0.0317 (7)	0.0024 (6)	0.0120 (6)	−0.0037 (6)
C10	0.0678 (12)	0.0427 (10)	0.0818 (13)	−0.0062 (9)	0.0305 (11)	0.0124 (10)
C1'	0.0361 (8)	0.0315 (7)	0.0463 (8)	−0.0001 (6)	0.0176 (7)	−0.0041 (7)
C2'	0.0389 (8)	0.0347 (8)	0.0493 (9)	−0.0009 (6)	0.0217 (7)	0.0001 (7)
O2'	0.0522 (6)	0.0483 (7)	0.0443 (6)	0.0107 (5)	0.0242 (5)	0.0017 (5)
C3'	0.0542 (10)	0.0445 (9)	0.0574 (10)	0.0042 (8)	0.0353 (9)	−0.0015 (8)
C4'	0.0529 (10)	0.0408 (9)	0.0753 (12)	0.0102 (8)	0.0388 (10)	0.0004 (9)
C5'	0.0445 (9)	0.0408 (9)	0.0623 (11)	0.0094 (7)	0.0207 (8)	0.0033 (8)
C6'	0.0418 (8)	0.0356 (8)	0.0487 (9)	0.0010 (7)	0.0162 (7)	−0.0045 (7)
O6'	0.0695 (8)	0.0590 (8)	0.0417 (6)	0.0255 (6)	0.0131 (6)	−0.0009 (6)
C12	0.0575 (10)	0.0465 (10)	0.0509 (10)	0.0044 (8)	0.0101 (8)	0.0066 (8)
C11	0.0676 (11)	0.0585 (11)	0.0481 (10)	0.0069 (9)	0.0301 (9)	0.0014 (8)

O1—C2	1.3549 (19)	C10—H10B	0.9600
O1—C5A	1.3692 (17)	C10—H10C	0.9600
C2—C3	1.331 (2)	C1'—C2'	1.388 (2)
C2—C1'	1.475 (2)	C1'—C6'	1.394 (2)
C3—C4	1.429 (2)	C2'—O2'	1.3555 (19)
C3—H3	0.9300	C2'—C3'	1.384 (2)
C4—O4	1.2500 (18)	O2'—C11	1.415 (2)
C4—C5	1.431 (2)	C3'—C4'	1.369 (2)
C5—C5A	1.384 (2)	C3'—H3'	0.9300
C5—C6	1.413 (2)	C4'—C5'	1.363 (3)
C6—O6	1.3445 (18)	C4'—H4'	0.9300
C6—C7	1.360 (2)	C5'—C6'	1.381 (2)
O6—H6	0.8200	C5'—H5'	0.9300
C7—C8	1.390 (2)	C6'—O6'	1.346 (2)
C7—H7	0.9300	O6'—C12	1.413 (2)
C8—O8	1.347 (2)	C12—H12A	0.9600
C8—C9	1.380 (2)	C12—H12B	0.9600
O8—C10	1.418 (2)	C12—H12C	0.9600
C9—C5A	1.376 (2)	C11—H11A	0.9600
C9—H9	0.9300	C11—H11B	0.9600
C10—H10A	0.9600	C11—H11C	0.9600
C2—O1—C5A	119.25 (11)	H10A—C10—H10C	109.5
C3—C2—O1	122.42 (13)	H10B—C10—H10C	109.5
C3—C2—C1'	124.37 (14)	C2'—C1'—C6'	118.90 (13)
O1—C2—C1'	113.21 (12)	C2'—C1'—C2	121.52 (13)
C2—C3—C4	121.93 (14)	C6'—C1'—C2	119.49 (13)
C2—C3—H3	119.0	O2'—C2'—C3'	124.56 (14)
C4—C3—H3	119.0	O2'—C2'—C1'	115.41 (13)
O4—C4—C3	122.98 (14)	C3'—C2'—C1'	120.03 (14)
O4—C4—C5	122.11 (13)	C2'—O2'—C11	117.66 (12)
C3—C4—C5	114.91 (13)	C4'—C3'—C2'	119.54 (15)
C5A—C5—C6	117.44 (13)	C4'—C3'—H3'	120.2
C5A—C5—C4	120.55 (13)	C2'—C3'—H3'	120.2
C6—C5—C4	122.00 (13)	C5'—C4'—C3'	121.82 (15)
O6—C6—C7	120.24 (13)	C5'—C4'—H4'	119.1
O6—C6—C5	119.10 (14)	C3'—C4'—H4'	119.1
C7—C6—C5	120.66 (14)	C4'—C5'—C6'	118.98 (16)
C6—O6—H6	109.5	C4'—C5'—H5'	120.5
C6—C7—C8	119.78 (14)	C6'—C5'—H5'	120.5
C6—C7—H7	120.1	O6'—C6'—C5'	124.35 (15)
C8—C7—H7	120.1	O6'—C6'—C1'	114.93 (13)
O8—C8—C9	123.71 (14)	C5'—C6'—C1'	120.72 (15)
O8—C8—C7	114.82 (13)	C6'—O6'—C12	119.16 (13)
C9—C8—C7	121.46 (14)	O6'—C12—H12A	109.5
C8—O8—C10	118.13 (13)	O6'—C12—H12B	109.5
C5A—C9—C8	117.69 (14)	H12A—C12—H12B	109.5
C5A—C9—H9	121.2	O6'—C12—H12C	109.5
C8—C9—H9	121.2	H12A—C12—H12C	109.5
O1—C5A—C9	116.19 (13)	H12B—C12—H12C	109.5
O1—C5A—C5	120.86 (13)	O2'—C11—H11A	109.5
C9—C5A—C5	122.94 (13)	O2'—C11—H11B	109.5
O8—C10—H10A	109.5	H11A—C11—H11B	109.5
O8—C10—H10B	109.5	O2'—C11—H11C	109.5
H10A—C10—H10B	109.5	H11A—C11—H11C	109.5
O8—C10—H10C	109.5	H11B—C11—H11C	109.5
C5A—O1—C2—C3	2.1 (2)	C6—C5—C5A—O1	178.64 (12)
C5A—O1—C2—C1'	−178.43 (12)	C4—C5—C5A—O1	−0.9 (2)
O1—C2—C3—C4	−0.2 (2)	C6—C5—C5A—C9	0.0 (2)
C1'—C2—C3—C4	−179.53 (14)	C4—C5—C5A—C9	−179.56 (14)
C2—C3—C4—O4	178.26 (15)	C3—C2—C1'—C2'	−115.93 (18)
C2—C3—C4—C5	−2.2 (2)	O1—C2—C1'—C2'	64.66 (18)
O4—C4—C5—C5A	−177.77 (14)	C3—C2—C1'—C6'	60.8 (2)
C3—C4—C5—C5A	2.7 (2)	O1—C2—C1'—C6'	−118.64 (15)
O4—C4—C5—C6	2.7 (2)	C6'—C1'—C2'—O2'	−179.85 (13)
C3—C4—C5—C6	−176.84 (14)	C2—C1'—C2'—O2'	−3.1 (2)
C5A—C5—C6—O6	178.63 (13)	C6'—C1'—C2'—C3'	−1.0 (2)
C4—C5—C6—O6	−1.8 (2)	C2—C1'—C2'—C3'	175.73 (14)
C5A—C5—C6—C7	−1.4 (2)	C3'—C2'—O2'—C11	−2.1 (2)
C4—C5—C6—C7	178.17 (15)	C1'—C2'—O2'—C11	176.67 (14)
O6—C6—C7—C8	−178.61 (14)	O2'—C2'—C3'—C4'	179.69 (15)
C5—C6—C7—C8	1.4 (2)	C1'—C2'—C3'—C4'	0.9 (2)
C6—C7—C8—O8	−179.87 (14)	C2'—C3'—C4'—C5'	0.2 (3)
C6—C7—C8—C9	0.0 (2)	C3'—C4'—C5'—C6'	−1.2 (3)
C9—C8—O8—C10	2.3 (2)	C4'—C5'—C6'—O6'	−178.63 (15)
C7—C8—O8—C10	−177.86 (15)	C4'—C5'—C6'—C1'	1.2 (2)
O8—C8—C9—C5A	178.53 (14)	C2'—C1'—C6'—O6'	179.76 (13)
C7—C8—C9—C5A	−1.3 (2)	C2—C1'—C6'—O6'	3.0 (2)
C2—O1—C5A—C9	177.17 (13)	C2'—C1'—C6'—C5'	−0.1 (2)
C2—O1—C5A—C5	−1.57 (19)	C2—C1'—C6'—C5'	−176.86 (14)
C8—C9—C5A—O1	−177.40 (12)	C5'—C6'—O6'—C12	−2.9 (2)
C8—C9—C5A—C5	1.3 (2)	C1'—C6'—O6'—C12	177.24 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O4	0.82	1.82	2.560 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O4	0.82	1.82	2.560 (2)	149