Poly[(μ-5,7-dihydr-oxy-4-oxo-2-phenyl-4H-chromene-8-sulfonato)potassium(I)].

In the polymeric title compound, [K(C(15)H(9)O(7)S)](n), the potassium cation is five-coordinated by four sulfonate O atoms and one carbonyl O atom. Two intra-molecular O-H⋯O hydrogen bonds stabilize the conformation of the anion. The polymeric three-dimensional supra-molecular architecture is formed via coordination inter-actions and π-π stacking inter-actions involving centrosymmetrically related pyrone rings, with a centroid-centroid separation of 3.513 (2) Å.

Related literature

For biological activities of flavonoids, see: Aljancic et al. (1999 ▶); Habtemariam (1997 ▶); Knekt et al. (1997 ▶); Ko et al. (1998 ▶); Nkengfack et al. (1994 ▶); Sakaguchi et al. (1992 ▶). For related structures, see: Benedict et al. (2004 ▶); Li & Zhang (2008 ▶); Wang & Zhang (2005a ▶,b ▶); Zhang & Wang (2005a ▶,b ▶).

Experimental

Crystal data

[K(C15H9O7S)]

M = 372.38

Orthorhombic,

a = 19.0846 (19) Å

b = 20.6555 (19) Å

c = 7.5148 (7) Å

V = 2962.3 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.54 mm−1

T = 296 (2) K

0.37 × 0.20 × 0.13 mm

Data collection

Bruker SMART-1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.825, T max = 0.933

13998 measured reflections

2637 independent reflections

1746 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.152

S = 1.02

2637 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041779/rz2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041779/rz2268Isup2.hkl

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

[K(C15H9O7S)]	F(000) = 1520
Mr = 372.38	Dx = 1.670 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2056 reflections
a = 19.0846 (19) Å	θ = 2.9–20.9°
b = 20.6555 (19) Å	µ = 0.54 mm−1
c = 7.5148 (7) Å	T = 296 K
V = 2962.3 (5) Å3	Plate, colourless
Z = 8	0.37 × 0.20 × 0.13 mm

Bruker SMART-1000 CCD area-detector diffractometer	2637 independent reflections
Radiation source: fine-focus sealed tube	1746 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −21→22
Tmin = 0.825, Tmax = 0.933	k = −24→22
13998 measured reflections	l = −7→8

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.091P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2637 reflections	Δρmax = 0.26 e Å−3
220 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: none

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
K1	0.13853 (4)	0.30967 (3)	0.70530 (10)	0.0614 (3)
S1	0.15766 (5)	0.35454 (4)	0.23290 (12)	0.0609 (3)
O1	0.24816 (13)	0.46137 (12)	0.4226 (4)	0.0808 (8)
H1	0.2561	0.4241	0.3913	0.121*
O2	0.07320 (14)	0.61774 (10)	0.4594 (4)	0.0757 (8)
H2	0.0318	0.6235	0.4351	0.114*
O3	−0.04849 (13)	0.59352 (11)	0.3174 (3)	0.0681 (7)
O4	0.02313 (11)	0.41527 (10)	0.1793 (3)	0.0518 (6)
O5	0.14317 (13)	0.34558 (12)	0.0469 (3)	0.0711 (7)
O6	0.11604 (17)	0.31214 (11)	0.3432 (3)	0.0830 (8)
O7	0.23185 (16)	0.34965 (14)	0.2716 (4)	0.1005 (11)
C1	0.06796 (17)	0.45769 (15)	0.2611 (4)	0.0483 (8)
C2	0.13557 (17)	0.43436 (15)	0.2928 (4)	0.0510 (8)
C3	0.18152 (19)	0.47689 (16)	0.3815 (4)	0.0587 (8)
C4	0.15971 (19)	0.53813 (16)	0.4343 (5)	0.0637 (9)
H4	0.1910	0.5653	0.4928	0.076*
C5	0.09334 (19)	0.55884 (15)	0.4016 (4)	0.0574 (8)
C6	0.04475 (17)	0.51880 (14)	0.3107 (4)	0.0494 (8)
C7	−0.02559 (19)	0.53857 (15)	0.2717 (4)	0.0555 (9)
C8	−0.06835 (18)	0.49192 (16)	0.1810 (4)	0.0563 (8)
H8	−0.1140	0.5029	0.1495	0.068*
C9	−0.04401 (17)	0.43304 (15)	0.1409 (4)	0.0515 (8)
C10	−0.08112 (18)	0.38009 (16)	0.0517 (4)	0.0571 (8)
C11	−0.1517 (2)	0.3838 (2)	0.0188 (6)	0.0862 (13)
H11	−0.1761	0.4205	0.0549	0.103*
C12	−0.1872 (3)	0.3350 (2)	−0.0658 (8)	0.1055 (16)
H12	−0.2352	0.3384	−0.0857	0.127*
C13	−0.1515 (3)	0.2812 (2)	−0.1205 (6)	0.0930 (14)
H13	−0.1751	0.2485	−0.1806	0.112*
C14	−0.0811 (3)	0.27500 (18)	−0.0878 (6)	0.0805 (12)
H14	−0.0572	0.2380	−0.1237	0.097*
C15	−0.0457 (2)	0.32438 (16)	−0.0007 (4)	0.0654 (9)
H15	0.0019	0.3202	0.0229	0.079*

	U11	U22	U33	U12	U13	U23
K1	0.0902 (6)	0.0465 (5)	0.0474 (5)	0.0031 (3)	−0.0002 (4)	−0.0003 (3)
S1	0.0824 (7)	0.0503 (5)	0.0499 (6)	0.0108 (4)	−0.0088 (4)	−0.0111 (4)
O1	0.0802 (18)	0.0717 (17)	0.0906 (19)	0.0055 (13)	−0.0169 (15)	−0.0260 (15)
O2	0.110 (2)	0.0437 (13)	0.0731 (18)	0.0056 (13)	−0.0029 (16)	−0.0139 (12)
O3	0.0923 (18)	0.0503 (14)	0.0618 (15)	0.0184 (12)	0.0040 (12)	−0.0021 (11)
O4	0.0652 (14)	0.0425 (12)	0.0477 (13)	−0.0009 (10)	0.0000 (10)	−0.0024 (10)
O5	0.0899 (17)	0.0801 (17)	0.0432 (15)	0.0097 (13)	−0.0021 (11)	−0.0177 (12)
O6	0.144 (2)	0.0461 (14)	0.0583 (15)	0.0019 (14)	0.0097 (16)	0.0017 (12)
O7	0.089 (2)	0.089 (2)	0.124 (3)	0.0313 (16)	−0.0417 (18)	−0.0468 (17)
C1	0.065 (2)	0.0459 (18)	0.0340 (17)	−0.0041 (14)	0.0040 (14)	0.0003 (13)
C2	0.068 (2)	0.0476 (18)	0.0368 (17)	0.0016 (15)	−0.0004 (15)	−0.0012 (14)
C3	0.074 (2)	0.0527 (19)	0.050 (2)	−0.0003 (17)	−0.0002 (17)	−0.0027 (16)
C4	0.082 (3)	0.050 (2)	0.059 (2)	−0.0092 (17)	−0.0038 (18)	−0.0100 (17)
C5	0.084 (2)	0.0445 (18)	0.0434 (19)	−0.0014 (16)	0.0025 (17)	−0.0013 (15)
C6	0.069 (2)	0.0425 (17)	0.0366 (17)	0.0021 (15)	0.0032 (15)	0.0009 (13)
C7	0.083 (2)	0.0437 (18)	0.0395 (17)	0.0045 (16)	0.0111 (16)	0.0056 (14)
C8	0.067 (2)	0.055 (2)	0.047 (2)	0.0026 (16)	0.0066 (16)	0.0026 (15)
C9	0.063 (2)	0.0546 (19)	0.0368 (17)	−0.0023 (16)	0.0067 (15)	0.0058 (14)
C10	0.067 (2)	0.056 (2)	0.048 (2)	−0.0070 (16)	0.0021 (16)	0.0012 (16)
C11	0.080 (3)	0.080 (3)	0.099 (3)	−0.005 (2)	−0.006 (2)	−0.021 (3)
C12	0.081 (3)	0.096 (3)	0.139 (5)	−0.013 (3)	−0.012 (3)	−0.021 (3)
C13	0.106 (4)	0.088 (3)	0.085 (3)	−0.039 (3)	−0.015 (3)	−0.006 (3)
C14	0.116 (4)	0.057 (2)	0.069 (3)	−0.015 (2)	0.002 (2)	−0.0078 (19)
C15	0.085 (3)	0.059 (2)	0.052 (2)	−0.0076 (19)	−0.0020 (18)	0.0029 (17)

K1—O5i	2.674 (2)	C1—C2	1.398 (4)
K1—O6ii	2.754 (2)	C2—C3	1.409 (5)
K1—O7iii	2.655 (3)	C3—C4	1.389 (5)
K1—O3iv	2.642 (2)	C4—C5	1.359 (5)
K1—O6	2.756 (3)	C4—H4	0.9300
K1—S1ii	3.4177 (12)	C5—C6	1.418 (4)
S1—O5	1.437 (2)	C6—C7	1.433 (5)
S1—O6	1.444 (3)	C7—C8	1.435 (5)
S1—O7	1.449 (3)	C8—C9	1.336 (4)
S1—C2	1.760 (3)	C8—H8	0.9300
O1—C3	1.347 (4)	C9—C10	1.466 (4)
O1—H1	0.8200	C10—C11	1.371 (5)
O2—C5	1.348 (4)	C10—C15	1.391 (5)
O2—H2	0.8200	C11—C12	1.372 (6)
O3—C7	1.264 (4)	C11—H11	0.9300
O3—K1iv	2.642 (2)	C12—C13	1.366 (6)
O4—C9	1.364 (4)	C12—H12	0.9300
O4—C1	1.370 (4)	C13—C14	1.372 (6)
O5—K1v	2.674 (2)	C13—H13	0.9300
O6—K1vi	2.754 (2)	C14—C15	1.387 (5)
O7—K1vii	2.655 (3)	C14—H14	0.9300
C1—C6	1.389 (4)	C15—H15	0.9300
O3iv—K1—O7iii	112.50 (9)	C5—O2—H2	109.5
O3iv—K1—O5i	82.73 (7)	C7—O3—K1iv	152.5 (2)
O7iii—K1—O5i	72.70 (8)	C9—O4—C1	120.6 (2)
O3iv—K1—O6ii	127.89 (9)	S1—O5—K1v	167.47 (15)
O7iii—K1—O6ii	111.02 (10)	S1—O5—K1vi	77.73 (11)
O5i—K1—O6ii	84.11 (8)	K1v—O5—K1vi	94.19 (7)
O3iv—K1—O6	79.69 (8)	S1—O6—K1vi	104.63 (13)
O7iii—K1—O6	108.95 (10)	S1—O6—K1	119.49 (16)
O5i—K1—O6	161.50 (8)	K1vi—O6—K1	109.29 (8)
O6ii—K1—O6	111.35 (7)	S1—O7—K1vii	153.43 (16)
O3iv—K1—S1ii	145.54 (6)	O4—C1—C6	120.2 (3)
O7iii—K1—S1ii	101.41 (7)	O4—C1—C2	115.6 (3)
O5i—K1—S1ii	102.33 (6)	C6—C1—C2	124.2 (3)
O6ii—K1—S1ii	24.13 (6)	C1—C2—C3	116.1 (3)
O6—K1—S1ii	95.45 (5)	C1—C2—S1	120.0 (2)
O3iv—K1—O5ii	134.72 (7)	C3—C2—S1	123.8 (3)
O7iii—K1—O5ii	109.43 (8)	O1—C3—C4	115.7 (3)
O5i—K1—O5ii	126.38 (7)	O1—C3—C2	123.2 (3)
O6ii—K1—O5ii	43.85 (7)	C4—C3—C2	121.1 (3)
O6—K1—O5ii	71.21 (6)	C5—C4—C3	120.9 (3)
S1ii—K1—O5ii	24.25 (4)	C5—C4—H4	119.5
O3iv—K1—K1vi	111.17 (5)	C3—C4—H4	119.5
O7iii—K1—K1vi	109.12 (6)	O2—C5—C4	119.4 (3)
O5i—K1—K1vi	162.75 (6)	O2—C5—C6	119.7 (3)
O6ii—K1—K1vi	79.25 (6)	C4—C5—C6	120.9 (3)
O6—K1—K1vi	35.35 (5)	C1—C6—C5	116.8 (3)
S1ii—K1—K1vi	60.42 (2)	C1—C6—C7	120.2 (3)
O5ii—K1—K1vi	36.40 (4)	C5—C6—C7	123.0 (3)
O3iv—K1—K1ii	117.97 (5)	O3—C7—C8	122.4 (3)
O7iii—K1—K1ii	90.78 (8)	O3—C7—C6	121.6 (3)
O5i—K1—K1ii	49.41 (6)	C8—C7—C6	116.0 (3)
O6ii—K1—K1ii	35.37 (6)	C9—C8—C7	121.4 (3)
O6—K1—K1ii	146.71 (6)	C9—C8—H8	119.3
S1ii—K1—K1ii	53.48 (2)	C7—C8—H8	119.3
O5ii—K1—K1ii	77.10 (4)	C8—C9—O4	121.6 (3)
K1vi—K1—K1ii	113.47 (3)	C8—C9—C10	127.9 (3)
O3iv—K1—K1viii	160.42 (6)	O4—C9—C10	110.5 (3)
O7iii—K1—K1viii	49.44 (7)	C11—C10—C15	118.2 (3)
O5i—K1—K1viii	96.34 (5)	C11—C10—C9	121.0 (3)
O6ii—K1—K1viii	71.15 (7)	C15—C10—C9	120.8 (3)
O6—K1—K1viii	98.28 (6)	C10—C11—C12	121.9 (4)
S1ii—K1—K1viii	53.85 (2)	C10—C11—H11	119.1
O5ii—K1—K1viii	60.52 (4)	C12—C11—H11	119.1
K1vi—K1—K1viii	74.040 (15)	C13—C12—C11	119.4 (4)
K1ii—K1—K1viii	74.040 (15)	C13—C12—H12	120.3
O5—S1—O6	111.97 (16)	C11—C12—H12	120.3
O5—S1—O7	111.99 (17)	C12—C13—C14	120.7 (4)
O6—S1—O7	112.33 (19)	C12—C13—H13	119.6
O5—S1—C2	108.86 (15)	C14—C13—H13	119.6
O6—S1—C2	106.85 (15)	C13—C14—C15	119.5 (4)
O7—S1—C2	104.36 (16)	C13—C14—H14	120.3
O5—S1—K1vi	78.02 (11)	C15—C14—H14	120.3
O6—S1—K1vi	51.24 (10)	C14—C15—C10	120.3 (4)
O7—S1—K1vi	92.71 (12)	C14—C15—H15	119.8
C2—S1—K1vi	156.86 (12)	C10—C15—H15	119.8
C3—O1—H1	109.5
O6—S1—O5—K1v	−89.8 (8)	O5—S1—C2—C3	−127.7 (3)
O7—S1—O5—K1v	37.4 (8)	O6—S1—C2—C3	111.2 (3)
C2—S1—O5—K1v	152.3 (7)	O7—S1—C2—C3	−8.0 (3)
K1vi—S1—O5—K1v	−50.7 (7)	K1vi—S1—C2—C3	128.4 (3)
O6—S1—O5—K1vi	−39.14 (14)	C1—C2—C3—O1	179.6 (3)
O7—S1—O5—K1vi	88.08 (15)	S1—C2—C3—O1	2.9 (5)
C2—S1—O5—K1vi	−157.05 (13)	C1—C2—C3—C4	0.4 (5)
O5—S1—O6—K1vi	52.35 (18)	S1—C2—C3—C4	−176.3 (3)
O7—S1—O6—K1vi	−74.68 (17)	O1—C3—C4—C5	−179.4 (3)
C2—S1—O6—K1vi	171.45 (13)	C2—C3—C4—C5	−0.1 (5)
O5—S1—O6—K1	175.02 (14)	C3—C4—C5—O2	178.0 (3)
O7—S1—O6—K1	48.0 (2)	C3—C4—C5—C6	−0.8 (5)
C2—S1—O6—K1	−65.88 (19)	O4—C1—C6—C5	177.3 (3)
K1vi—S1—O6—K1	122.7 (2)	C2—C1—C6—C5	−1.0 (4)
O3iv—K1—O6—S1	86.63 (17)	O4—C1—C6—C7	−1.9 (4)
O7iii—K1—O6—S1	−23.78 (19)	C2—C1—C6—C7	179.7 (3)
O5i—K1—O6—S1	68.3 (4)	O2—C5—C6—C1	−177.4 (3)
O6ii—K1—O6—S1	−146.56 (11)	C4—C5—C6—C1	1.3 (5)
S1ii—K1—O6—S1	−127.83 (16)	O2—C5—C6—C7	1.8 (5)
O5ii—K1—O6—S1	−128.54 (18)	C4—C5—C6—C7	−179.5 (3)
K1vi—K1—O6—S1	−120.4 (2)	K1iv—O3—C7—C8	−19.5 (6)
K1ii—K1—O6—S1	−147.10 (9)	K1iv—O3—C7—C6	161.6 (3)
K1viii—K1—O6—S1	−73.63 (16)	C1—C6—C7—O3	179.0 (3)
O3iv—K1—O6—K1vi	−153.01 (12)	C5—C6—C7—O3	−0.2 (5)
O7iii—K1—O6—K1vi	96.58 (12)	C1—C6—C7—C8	0.0 (4)
O5i—K1—O6—K1vi	−171.4 (2)	C5—C6—C7—C8	−179.2 (3)
O6ii—K1—O6—K1vi	−26.21 (19)	O3—C7—C8—C9	−177.0 (3)
S1ii—K1—O6—K1vi	−7.48 (11)	C6—C7—C8—C9	1.9 (5)
O5ii—K1—O6—K1vi	−8.18 (9)	C7—C8—C9—O4	−2.0 (5)
K1ii—K1—O6—K1vi	−26.7 (2)	C7—C8—C9—C10	179.1 (3)
K1viii—K1—O6—K1vi	46.72 (11)	C1—O4—C9—C8	0.1 (4)
O5—S1—O7—K1vii	−24.2 (5)	C1—O4—C9—C10	179.1 (2)
O6—S1—O7—K1vii	102.8 (5)	C8—C9—C10—C11	−8.7 (5)
C2—S1—O7—K1vii	−141.8 (4)	O4—C9—C10—C11	172.3 (3)
K1vi—S1—O7—K1vii	54.0 (5)	C8—C9—C10—C15	171.8 (3)
C9—O4—C1—C6	1.9 (4)	O4—C9—C10—C15	−7.2 (4)
C9—O4—C1—C2	−179.6 (2)	C15—C10—C11—C12	−1.1 (6)
O4—C1—C2—C3	−178.2 (3)	C9—C10—C11—C12	179.5 (4)
C6—C1—C2—C3	0.2 (5)	C10—C11—C12—C13	−0.5 (8)
O4—C1—C2—S1	−1.4 (4)	C11—C12—C13—C14	1.6 (8)
C6—C1—C2—S1	177.0 (2)	C12—C13—C14—C15	−1.0 (7)
O5—S1—C2—C1	55.8 (3)	C13—C14—C15—C10	−0.6 (6)
O6—S1—C2—C1	−65.3 (3)	C11—C10—C15—C14	1.7 (5)
O7—S1—C2—C1	175.5 (3)	C9—C10—C15—C14	−178.9 (3)
K1vi—S1—C2—C1	−48.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7	0.82	1.84	2.588 (4)	152
O2—H2···O3	0.82	1.87	2.604 (4)	148

Table 1

Selected bond lengths (Å)

K1—O5i	2.674 (2)
K1—O6ii	2.754 (2)
K1—O7iii	2.655 (3)
K1—O3iv	2.642 (2)
K1—O6	2.756 (3)

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O7	0.82	1.84	2.588 (4)	152
O2—H2⋯O3	0.82	1.87	2.604 (4)	148

Symmetry codes: .