Poly[potassium-μ-2-[2-(carboxymethyl)phenyl]acetato]

García-Zarracino, R.; Rangel-Marrón, M.; Tlahuext, H.; Höpfl, H.

doi:10.1107/S1600536808038889

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1626

doi:10.1107/S1600536808038889

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Poly[potassium-μ-2-[2-(carboxymethyl)phenyl]acetato]

Reyes García-Zarracino,^a Marcela Rangel-Marrón,^a Hugo Tlahuext ^b ^* and Herbert Höpfl ^b

^aFacultad de Química, Universidad Autónoma del Carmen. Calle 56 No. 4, CP 24180, Cd. del Carmen, Campeche, México, and ^bCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos. Av. Universidad 1001 Col., Chamilpa, CP 62209, Cuernavaca Mor., México
^*Correspondence e-mail: tlahuext@ciq.uaem.mx

(Received 30 October 2008; accepted 19 November 2008; online 29 November 2008)

In the title salt, [K(C₁₀H₉O₄)]_n, the K⁺ ions are coordinated by six O atoms from three different anions, and there is a cation–π interaction at ca 3.14 Å. The 2-[2-(carboxymethyl)phenyl]acetate anions are stabilized by intramolecular O—H⋯O hydrogen bonds, and the K⁺ cations are linked into one-dimensional coordination polymers running along the b axis; these are further interconnected by weak C—H⋯O hydrogen bonds.

Related literature

For general background, see: Atwood & Steed (2004 ); Ma & Dougherty (1997 ); Kumpf & Dougherty (1993 ); Heginbotham et al. (1994 ). For coordination polymers, see: Chae et al. (2004 ); García-Zarracino et al. (2003 ); García-Zarracino & Höpfl (2004 ). For analysis of hydrogen-bonding patterns, see: Bernstein et al. (1995 ); Desiraju (2002 ).

Experimental

Crystal data

[K(C₁₀H₉O₄)]
M_r = 232.27
Monoclinic, P 2₁ /c
a = 8.3365 (14) Å
b = 6.7886 (11) Å
c = 17.651 (3) Å
β = 92.543 (3)°
V = 997.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 293 (2) K
0.45 × 0.30 × 0.28 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.713, T_max = 0.864
8711 measured reflections
1727 independent reflections
1560 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.101
S = 1.08
1727 reflections
139 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4′⋯O1ⁱ	1.01 (3)	2.57 (3)	3.248 (2)	125 (2)
O4—H4′⋯O2ⁱ	1.01 (3)	1.47 (3)	2.471 (2)	176 (3)
C2—H2A⋯O2ⁱⁱ	0.97	2.53	3.480 (3)	167
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+2, -z+1.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus-NT (Bruker, 2001 ); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: PLATON (Spek, 2003 ) and publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038889/sg2283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038889/sg2283Isup2.hkl

checkCIF report

Comment top

Hydrogen bonding, cation-π, and π-π interactions are principal forces which determine the structure, self-assembly and recognition in many chemical and biological systems (Atwood & Steed, 2004). Cation-π interactions are now recognized as important non-covalent binding forces in biological systems (Ma & Dougherty, 1997). It has been postulated that the aromatic side chains of amino acids might determine K⁺transport selectivity in transmembrane protein channels (Kumpf & Dougherty, 1993; Heginbotham et al., 1994).

In complex I each K⁺ion is coordinated by six oxygen atoms from three different ligand molecules and there is a cation···π interaction (Fig.1) forming a distorted square-face monocapped prism (Fig. 2). The centroid of the aryl ring (Cg, C3—C8) is situated 3.138 Å from the K⁺ ion [sum of ionic and van der Waals radii K⁺···C(Ar) 3.37 Å]. Since the K—C_arene contacts [C3—K= 3.344 (2), C4—K = 3.260 (2) and C5—K = 3.334 (2) Å] and [C6—K = 3.508 (2), C7—K = 3.596, C8—K = 3.511 (2)] the K-arene interaction can be regarded as η³-coordination. The oxygen atoms of the carboxyl and carboxylate groups are forming bridging units between two K⁺ cations, thus generating a one-dimensional coordination polymer, running along the b axis (Chae et al., 2004; García-Zarracino et al., 2003; García-Zarracino & Höpfl, 2004) (Fig. 2). The coordination polymer is stabilized by intramolecular O4—H4'···O2 hydrogen bonds. The crystal structure is stabilized by weak C—H···O hydogen bonds forming R₂²(8) motifs, (Bernstein et al., 1995; Desiraju, 2002) between adjacent coordination polymers (Fig. 3, Table 1).

Related literature top

For general background, see: Atwood & Steed (2004); Ma & Dougherty (1997); Kumpf & Dougherty (1993); Heginbotham et al. (1994). For coordination polymers, see: Chae et al. (2004); García-Zarracino et al. (2003); García-Zarracino & Höpfl (2004). For analysis of hydrogen-bonding patterns, see: Bernstein et al. (1995); Desiraju (2002).

Experimental top

Single Crystals of (I) were obtained by slow evaporation of a solution containning 1,2-phenylenediacetic acid (1.0 g, 5.15 mmol), potassium hydroxide (0.289 g, 5.15 mmol) in MeOH/H₂O (5:1).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT (Bruker, 2001); program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-NT (Sheldrick, 2008); molecular graphics: SHELXTL-NT (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2003) and publCIF (Westrip, 2008).

Figures top

	Fig. 1. Asymmetric unit of I showing 50% probability displacement ellipsoids and the atomic numbering. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. View of the one-dimensional coordination polymer chain running along to the b axis. Dashed and dotted lines indicate C_aryl···K⁺ and O—H···O contacts, respectively. H atoms not involved in hydrogen-bonding have been omitted for clarity.
	Fig. 3. View of the C—H···O hydogen bonds forming R₂²(8) motifs between adjacent coordination polymers. The hydrogen bonds are represented by dotted lines and H atoms not involved in hydrogen- bonding have been omitted for clarity.

Poly[potassium-µ-2-[2-(carboxymethyl)phenyl]acetato] top

Crystal data top

[K(C₁₀H₉O₄)]	F(000) = 480
M_r = 232.27	D_x = 1.546 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4833 reflections
a = 8.3365 (14) Å	θ = 2.3–28.2°
b = 6.7886 (11) Å	µ = 0.52 mm⁻¹
c = 17.651 (3) Å	T = 293 K
β = 92.543 (3)°	Rectangular, colourless
V = 997.9 (3) Å³	0.45 × 0.30 × 0.28 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1727 independent reflections
Radiation source: fine-focus sealed tube	1560 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.713, T_max = 0.864	k = −8→8
8711 measured reflections	l = −20→20

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0462P)² + 0.3852P] where P = (F_o² + 2F_c²)/3
1727 reflections	(Δ/σ)_max = 0.001
139 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

[K(C₁₀H₉O₄)]	V = 997.9 (3) Å³
M_r = 232.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3365 (14) Å	µ = 0.52 mm⁻¹
b = 6.7886 (11) Å	T = 293 K
c = 17.651 (3) Å	0.45 × 0.30 × 0.28 mm
β = 92.543 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1727 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1560 reflections with I > 2σ(I)
T_min = 0.713, T_max = 0.864	R_int = 0.039
8711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.21 e Å⁻³
1727 reflections	Δρ_min = −0.20 e Å⁻³
139 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
K1	0.38073 (6)	0.33470 (7)	0.44502 (3)	0.0455 (2)
O1	0.2998 (2)	0.6914 (2)	0.51210 (9)	0.0487 (4)
O2	0.26242 (19)	1.0124 (2)	0.52043 (9)	0.0449 (4)
O3	0.5412 (2)	0.6608 (2)	0.38998 (11)	0.0569 (5)
O4	0.5243 (2)	0.9834 (2)	0.37776 (9)	0.0471 (4)
H4'	0.612 (4)	0.991 (4)	0.4186 (16)	0.071*
C1	0.2360 (3)	0.8431 (3)	0.49014 (12)	0.0350 (5)
C2	0.1154 (3)	0.8450 (3)	0.42353 (13)	0.0449 (6)
H2A	0.0091	0.8637	0.4426	0.054*
H2B	0.1379	0.9572	0.3917	0.054*
C3	0.1135 (3)	0.6626 (3)	0.37550 (12)	0.0362 (5)
C4	0.2223 (3)	0.6353 (3)	0.31858 (12)	0.0378 (5)
C5	0.2138 (3)	0.4620 (4)	0.27695 (12)	0.0458 (6)
H5	0.2859	0.4419	0.2389	0.055*
C6	0.1017 (3)	0.3192 (4)	0.29041 (14)	0.0495 (6)
H6	0.0988	0.2039	0.2619	0.059*
C7	−0.0052 (3)	0.3471 (3)	0.34570 (14)	0.0498 (6)
H7	−0.0816	0.2512	0.3549	0.060*
C8	0.0006 (3)	0.5179 (3)	0.38770 (13)	0.0434 (6)
H8	−0.0730	0.5365	0.4251	0.052*
C9	0.3453 (3)	0.7892 (4)	0.30161 (13)	0.0497 (6)
H9A	0.2919	0.9158	0.2963	0.060*
H9B	0.3909	0.7583	0.2534	0.060*
C10	0.4803 (3)	0.8065 (3)	0.36163 (12)	0.0393 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0465 (3)	0.0342 (3)	0.0548 (3)	0.0001 (2)	−0.0082 (2)	0.0024 (2)
O1	0.0540 (10)	0.0367 (9)	0.0542 (10)	0.0060 (8)	−0.0139 (8)	−0.0016 (7)
O2	0.0498 (10)	0.0346 (8)	0.0497 (9)	0.0011 (7)	−0.0047 (7)	−0.0062 (7)
O3	0.0503 (10)	0.0450 (10)	0.0735 (12)	−0.0046 (8)	−0.0172 (9)	0.0114 (9)
O4	0.0466 (10)	0.0432 (9)	0.0508 (9)	−0.0003 (7)	−0.0053 (8)	0.0004 (7)
C1	0.0315 (11)	0.0362 (12)	0.0379 (11)	−0.0003 (9)	0.0064 (9)	0.0003 (9)
C2	0.0455 (13)	0.0393 (13)	0.0492 (13)	0.0099 (10)	−0.0077 (11)	−0.0032 (10)
C3	0.0352 (11)	0.0354 (11)	0.0372 (11)	0.0058 (9)	−0.0090 (9)	−0.0001 (9)
C4	0.0335 (11)	0.0442 (12)	0.0350 (11)	0.0027 (9)	−0.0077 (9)	0.0037 (9)
C5	0.0416 (13)	0.0596 (15)	0.0357 (12)	0.0124 (11)	−0.0051 (10)	−0.0076 (11)
C6	0.0541 (15)	0.0428 (14)	0.0498 (14)	0.0022 (11)	−0.0170 (12)	−0.0106 (11)
C7	0.0502 (14)	0.0435 (13)	0.0542 (15)	−0.0105 (11)	−0.0139 (12)	0.0053 (11)
C8	0.0387 (13)	0.0508 (14)	0.0405 (12)	−0.0034 (10)	−0.0013 (10)	0.0031 (10)
C9	0.0455 (14)	0.0583 (15)	0.0446 (13)	−0.0076 (12)	−0.0052 (11)	0.0133 (11)
C10	0.0339 (12)	0.0448 (14)	0.0395 (12)	−0.0037 (10)	0.0056 (9)	0.0053 (10)

Geometric parameters (Å, º) top

K1—O1ⁱ	2.7422 (17)	O4—H4'	1.00 (3)
K1—O2ⁱⁱ	2.7654 (17)	C1—C2	1.513 (3)
K1—O3	2.7837 (18)	C2—C3	1.500 (3)
K1—O1	2.7912 (16)	C2—H2A	0.9700
K1—O4ⁱⁱ	2.9419 (17)	C2—H2B	0.9700
K1—O3ⁱ	2.956 (2)	C3—C8	1.384 (3)
K1—C4	3.260 (2)	C3—C4	1.396 (3)
K1—C5	3.334 (2)	C4—C5	1.387 (3)
K1—C3	3.344 (2)	C4—C9	1.503 (3)
K1—C6	3.508 (2)	C5—C6	1.374 (3)
K1—C8	3.511 (2)	C5—H5	0.9300
K1—K1ⁱ	3.5235 (10)	C6—C7	1.364 (4)
O1—C1	1.215 (2)	C6—H6	0.9300
O1—K1ⁱ	2.7422 (17)	C7—C8	1.376 (3)
O2—C1	1.282 (2)	C7—H7	0.9300
O2—K1ⁱⁱⁱ	2.7654 (17)	C8—H8	0.9300
O3—C10	1.210 (3)	C9—C10	1.515 (3)
O3—K1ⁱ	2.956 (2)	C9—H9A	0.9700
O4—C10	1.284 (3)	C9—H9B	0.9700
O4—K1ⁱⁱⁱ	2.9420 (17)

O1ⁱ—K1—O2ⁱⁱ	100.31 (5)	C8—K1—K1ⁱ	114.41 (4)
O1ⁱ—K1—O3	70.84 (5)	C1—O1—K1ⁱ	123.28 (14)
O2ⁱⁱ—K1—O3	169.83 (5)	C1—O1—K1	135.31 (14)
O1ⁱ—K1—O1	100.90 (5)	K1ⁱ—O1—K1	79.10 (5)
O2ⁱⁱ—K1—O1	112.58 (5)	C1—O2—K1ⁱⁱⁱ	124.52 (13)
O3—K1—O1	65.62 (6)	C10—O3—K1	126.51 (15)
O1ⁱ—K1—O4ⁱⁱ	69.61 (5)	C10—O3—K1ⁱ	117.98 (15)
O2ⁱⁱ—K1—O4ⁱⁱ	73.33 (5)	K1—O3—K1ⁱ	75.67 (5)
O3—K1—O4ⁱⁱ	107.07 (6)	C10—O4—K1ⁱⁱⁱ	136.90 (14)
O1—K1—O4ⁱⁱ	169.97 (5)	C10—O4—H4'	113.6 (16)
O1ⁱ—K1—O3ⁱ	63.90 (5)	K1ⁱⁱⁱ—O4—H4'	87.9 (16)
O2ⁱⁱ—K1—O3ⁱ	66.52 (5)	O1—C1—O2	124.2 (2)
O3—K1—O3ⁱ	104.32 (5)	O1—C1—C2	121.41 (19)
O1—K1—O3ⁱ	67.66 (5)	O2—C1—C2	114.38 (18)
O4ⁱⁱ—K1—O3ⁱ	109.28 (5)	C3—C2—C1	114.97 (18)
O1ⁱ—K1—C4	126.04 (6)	C3—C2—H2A	108.5
O2ⁱⁱ—K1—C4	133.04 (5)	C1—C2—H2A	108.5
O3—K1—C4	56.60 (5)	C3—C2—H2B	108.5
O1—K1—C4	69.46 (5)	C1—C2—H2B	108.5
O4ⁱⁱ—K1—C4	113.01 (5)	H2A—C2—H2B	107.5
O3ⁱ—K1—C4	137.12 (5)	C8—C3—C4	119.1 (2)
O1ⁱ—K1—C5	128.62 (6)	C8—C3—C2	119.2 (2)
O2ⁱⁱ—K1—C5	119.32 (6)	C4—C3—C2	121.7 (2)
O3—K1—C5	70.82 (6)	C8—C3—K1	85.25 (13)
O1—K1—C5	93.06 (5)	C4—C3—K1	74.46 (11)
O4ⁱⁱ—K1—C5	90.70 (5)	C2—C3—K1	110.62 (12)
O3ⁱ—K1—C5	159.86 (6)	C5—C4—C3	118.3 (2)
C4—K1—C5	24.26 (6)	C5—C4—C9	120.2 (2)
O1ⁱ—K1—C3	140.12 (5)	C3—C4—C9	121.5 (2)
O2ⁱⁱ—K1—C3	117.21 (5)	C5—C4—K1	80.87 (12)
O3—K1—C3	70.43 (5)	C3—C4—K1	81.18 (12)
O1—K1—C3	53.74 (5)	C9—C4—K1	108.22 (13)
O4ⁱⁱ—K1—C3	131.90 (5)	C6—C5—C4	121.7 (2)
O3ⁱ—K1—C3	117.95 (5)	C6—C5—K1	85.62 (14)
C4—K1—C3	24.36 (5)	C4—C5—K1	74.87 (12)
C5—K1—C3	41.93 (5)	C6—C5—H5	119.1
O1ⁱ—K1—C6	144.60 (6)	C4—C5—H5	119.1
O2ⁱⁱ—K1—C6	96.45 (6)	K1—C5—H5	110.3
O3—K1—C6	93.71 (6)	C7—C6—C5	119.8 (2)
O1—K1—C6	101.04 (5)	C7—C6—K1	82.60 (14)
O4ⁱⁱ—K1—C6	85.95 (5)	C5—C6—K1	71.39 (13)
O3ⁱ—K1—C6	151.19 (6)	C7—C6—H6	120.1
C4—K1—C6	41.56 (6)	C5—C6—H6	120.1
C5—K1—C6	23.00 (6)	K1—C6—H6	116.5
C3—K1—C6	47.66 (5)	C6—C7—C8	119.6 (2)
O1ⁱ—K1—C8	162.86 (5)	C6—C7—K1	75.30 (14)
O2ⁱⁱ—K1—C8	94.72 (5)	C8—C7—K1	75.38 (13)
O3—K1—C8	93.40 (5)	C6—C7—H7	120.2
O1—K1—C8	65.34 (5)	C8—C7—H7	120.2
O4ⁱⁱ—K1—C8	123.29 (5)	K1—C7—H7	120.2
O3ⁱ—K1—C8	115.89 (5)	C7—C8—C3	121.5 (2)
C4—K1—C8	41.24 (5)	C7—C8—K1	82.34 (14)
C5—K1—C8	46.86 (6)	C3—C8—K1	71.62 (12)
C3—K1—C8	23.13 (5)	C7—C8—H8	119.3
C6—K1—C8	39.43 (6)	C3—C8—H8	119.3
O1ⁱ—K1—K1ⁱ	51.07 (3)	K1—C8—H8	117.3
O2ⁱⁱ—K1—K1ⁱ	116.32 (4)	C4—C9—C10	113.96 (18)
O3—K1—K1ⁱ	54.37 (4)	C4—C9—H9A	108.8
O1—K1—K1ⁱ	49.84 (4)	C10—C9—H9A	108.8
O4ⁱⁱ—K1—K1ⁱ	120.59 (4)	C4—C9—H9B	108.8
O3ⁱ—K1—K1ⁱ	49.95 (3)	C10—C9—H9B	108.8
C4—K1—K1ⁱ	100.37 (4)	H9A—C9—H9B	107.7
C5—K1—K1ⁱ	121.87 (5)	O3—C10—O4	124.2 (2)
C3—K1—K1ⁱ	97.39 (4)	O3—C10—C9	120.7 (2)
C6—K1—K1ⁱ	141.83 (5)	O4—C10—C9	115.0 (2)

O1ⁱ—K1—O1—C1	126.9 (2)	C3—K1—C4—C9	120.3 (2)
O2ⁱⁱ—K1—O1—C1	−127.0 (2)	C6—K1—C4—C9	−147.96 (19)
O3—K1—O1—C1	63.9 (2)	C8—K1—C4—C9	150.69 (19)
O4ⁱⁱ—K1—O1—C1	108.4 (3)	K1ⁱ—K1—C4—C9	35.31 (16)
O3ⁱ—K1—O1—C1	−177.4 (2)	C3—C4—C5—C6	0.2 (3)
C4—K1—O1—C1	2.3 (2)	C9—C4—C5—C6	−179.2 (2)
C5—K1—O1—C1	−3.4 (2)	K1—C4—C5—C6	74.9 (2)
C3—K1—O1—C1	−19.0 (2)	C3—C4—C5—K1	−74.75 (17)
C6—K1—O1—C1	−25.2 (2)	C9—C4—C5—K1	105.83 (18)
C8—K1—O1—C1	−42.4 (2)	O1ⁱ—K1—C5—C6	142.02 (14)
K1ⁱ—K1—O1—C1	126.9 (2)	O2ⁱⁱ—K1—C5—C6	6.69 (16)
O1ⁱ—K1—O1—K1ⁱ	0.0	O3—K1—C5—C6	−174.26 (16)
O2ⁱⁱ—K1—O1—K1ⁱ	106.11 (5)	O1—K1—C5—C6	−111.41 (15)
O3—K1—O1—K1ⁱ	−62.98 (5)	O4ⁱⁱ—K1—C5—C6	77.89 (14)
O4ⁱⁱ—K1—O1—K1ⁱ	−18.4 (3)	O3ⁱ—K1—C5—C6	−95.1 (2)
O3ⁱ—K1—O1—K1ⁱ	55.70 (5)	C4—K1—C5—C6	−124.5 (2)
C4—K1—O1—K1ⁱ	−124.58 (6)	C3—K1—C5—C6	−92.50 (16)
C5—K1—O1—K1ⁱ	−130.30 (6)	C8—K1—C5—C6	−59.92 (14)
C3—K1—O1—K1ⁱ	−145.89 (8)	K1ⁱ—K1—C5—C6	−154.75 (13)
C6—K1—O1—K1ⁱ	−152.05 (6)	O1ⁱ—K1—C5—C4	−93.44 (14)
C8—K1—O1—K1ⁱ	−169.22 (6)	O2ⁱⁱ—K1—C5—C4	131.23 (13)
O1ⁱ—K1—O3—C10	−169.7 (2)	O3—K1—C5—C4	−49.72 (14)
O2ⁱⁱ—K1—O3—C10	−139.5 (3)	O1—K1—C5—C4	13.13 (14)
O1—K1—O3—C10	−57.54 (19)	O4ⁱⁱ—K1—C5—C4	−157.57 (14)
O4ⁱⁱ—K1—O3—C10	129.80 (19)	O3ⁱ—K1—C5—C4	29.4 (3)
O3ⁱ—K1—O3—C10	−114.4 (2)	C3—K1—C5—C4	32.04 (12)
C4—K1—O3—C10	23.11 (18)	C6—K1—C5—C4	124.5 (2)
C5—K1—O3—C10	45.16 (19)	C8—K1—C5—C4	64.62 (13)
C3—K1—O3—C10	0.58 (19)	K1ⁱ—K1—C5—C4	−30.21 (15)
C6—K1—O3—C10	42.9 (2)	C4—C5—C6—C7	0.3 (3)
C8—K1—O3—C10	3.4 (2)	K1—C5—C6—C7	69.5 (2)
K1ⁱ—K1—O3—C10	−114.4 (2)	C4—C5—C6—K1	−69.20 (19)
O1ⁱ—K1—O3—K1ⁱ	−55.29 (4)	O1ⁱ—K1—C6—C7	178.97 (13)
O2ⁱⁱ—K1—O3—K1ⁱ	−25.1 (3)	O2ⁱⁱ—K1—C6—C7	60.94 (15)
O1—K1—O3—K1ⁱ	56.88 (4)	O3—K1—C6—C7	−119.50 (15)
O4ⁱⁱ—K1—O3—K1ⁱ	−115.78 (5)	O1—K1—C6—C7	−53.63 (15)
O3ⁱ—K1—O3—K1ⁱ	0.0	O4ⁱⁱ—K1—C6—C7	133.63 (15)
C4—K1—O3—K1ⁱ	137.53 (7)	O3ⁱ—K1—C6—C7	9.7 (2)
C5—K1—O3—K1ⁱ	159.58 (6)	C4—K1—C6—C7	−94.26 (16)
C3—K1—O3—K1ⁱ	115.00 (6)	C5—K1—C6—C7	−124.9 (2)
C6—K1—O3—K1ⁱ	157.33 (5)	C3—K1—C6—C7	−60.36 (14)
C8—K1—O3—K1ⁱ	117.82 (5)	C8—K1—C6—C7	−28.65 (13)
K1ⁱ—O1—C1—O2	−42.1 (3)	K1ⁱ—K1—C6—C7	−89.04 (16)
K1—O1—C1—O2	−152.13 (16)	O1ⁱ—K1—C6—C5	−56.10 (18)
K1ⁱ—O1—C1—C2	138.33 (17)	O2ⁱⁱ—K1—C6—C5	−174.13 (14)
K1—O1—C1—C2	28.3 (3)	O3—K1—C6—C5	5.43 (15)
K1ⁱⁱⁱ—O2—C1—O1	120.5 (2)	O1—K1—C6—C5	71.30 (15)
K1ⁱⁱⁱ—O2—C1—C2	−60.0 (2)	O4ⁱⁱ—K1—C6—C5	−101.44 (14)
O1—C1—C2—C3	−15.3 (3)	O3ⁱ—K1—C6—C5	134.65 (15)
O2—C1—C2—C3	165.1 (2)	C4—K1—C6—C5	30.67 (13)
C1—C2—C3—C8	97.3 (2)	C3—K1—C6—C5	64.57 (14)
C1—C2—C3—C4	−83.0 (3)	C8—K1—C6—C5	96.28 (16)
C1—C2—C3—K1	1.1 (2)	K1ⁱ—K1—C6—C5	35.89 (18)
O1ⁱ—K1—C3—C8	−172.79 (12)	C5—C6—C7—C8	−0.2 (3)
O2ⁱⁱ—K1—C3—C8	−14.49 (15)	K1—C6—C7—C8	63.3 (2)
O3—K1—C3—C8	172.82 (15)	C5—C6—C7—K1	−63.6 (2)
O1—K1—C3—C8	−113.60 (15)	O1ⁱ—K1—C7—C6	−2.6 (3)
O4ⁱⁱ—K1—C3—C8	77.11 (15)	O2ⁱⁱ—K1—C7—C6	−119.40 (15)
O3ⁱ—K1—C3—C8	−90.94 (13)	O3—K1—C7—C6	63.61 (15)
C4—K1—C3—C8	121.97 (19)	O1—K1—C7—C6	127.72 (15)
C5—K1—C3—C8	90.07 (15)	O4ⁱⁱ—K1—C7—C6	−47.38 (15)
C6—K1—C3—C8	58.20 (14)	O3ⁱ—K1—C7—C6	−173.97 (13)
K1ⁱ—K1—C3—C8	−139.20 (13)	C4—K1—C7—C6	63.69 (15)
O1ⁱ—K1—C3—C4	65.24 (15)	C5—K1—C7—C6	30.06 (14)
O2ⁱⁱ—K1—C3—C4	−136.46 (12)	C3—K1—C7—C6	97.57 (17)
O3—K1—C3—C4	50.85 (12)	C8—K1—C7—C6	126.6 (2)
O1—K1—C3—C4	124.43 (14)	K1ⁱ—K1—C7—C6	116.29 (14)
O4ⁱⁱ—K1—C3—C4	−44.86 (15)	O1ⁱ—K1—C7—C8	−129.2 (2)
O3ⁱ—K1—C3—C4	147.09 (12)	O2ⁱⁱ—K1—C7—C8	114.02 (14)
C5—K1—C3—C4	−31.90 (12)	O3—K1—C7—C8	−62.96 (15)
C6—K1—C3—C4	−63.77 (13)	O1—K1—C7—C8	1.15 (14)
C8—K1—C3—C4	−121.97 (19)	O4ⁱⁱ—K1—C7—C8	−173.96 (14)
K1ⁱ—K1—C3—C4	98.82 (12)	O3ⁱ—K1—C7—C8	59.46 (16)
O1ⁱ—K1—C3—C2	−53.34 (19)	C4—K1—C7—C8	−62.89 (14)
O2ⁱⁱ—K1—C3—C2	104.95 (15)	C5—K1—C7—C8	−96.52 (16)
O3—K1—C3—C2	−67.73 (15)	C3—K1—C7—C8	−29.00 (13)
O1—K1—C3—C2	5.85 (14)	C6—K1—C7—C8	−126.6 (2)
O4ⁱⁱ—K1—C3—C2	−163.45 (14)	K1ⁱ—K1—C7—C8	−10.29 (18)
O3ⁱ—K1—C3—C2	28.50 (17)	C6—C7—C8—C3	−0.4 (3)
C4—K1—C3—C2	−118.6 (2)	K1—C7—C8—C3	62.90 (19)
C5—K1—C3—C2	−150.48 (19)	C6—C7—C8—K1	−63.3 (2)
C6—K1—C3—C2	177.65 (19)	C4—C3—C8—C7	0.9 (3)
C8—K1—C3—C2	119.4 (2)	C2—C3—C8—C7	−179.4 (2)
K1ⁱ—K1—C3—C2	−19.76 (16)	K1—C3—C8—C7	−68.4 (2)
C8—C3—C4—C5	−0.8 (3)	C4—C3—C8—K1	69.28 (17)
C2—C3—C4—C5	179.52 (19)	C2—C3—C8—K1	−111.00 (18)
K1—C3—C4—C5	74.57 (17)	O1ⁱ—K1—C8—C7	142.7 (2)
C8—C3—C4—C9	178.6 (2)	O2ⁱⁱ—K1—C8—C7	−66.03 (14)
C2—C3—C4—C9	−1.1 (3)	O3—K1—C8—C7	120.10 (14)
K1—C3—C4—C9	−106.02 (19)	O1—K1—C8—C7	−178.74 (15)
C8—C3—C4—K1	−75.34 (18)	O4ⁱⁱ—K1—C8—C7	7.10 (16)
C2—C3—C4—K1	104.94 (18)	O3ⁱ—K1—C8—C7	−132.18 (14)
O1ⁱ—K1—C4—C5	105.32 (14)	C4—K1—C8—C7	94.82 (16)
O2ⁱⁱ—K1—C4—C5	−63.79 (16)	C5—K1—C8—C7	60.55 (15)
O3—K1—C4—C5	120.34 (15)	C3—K1—C8—C7	126.9 (2)
O1—K1—C4—C5	−165.98 (15)	C6—K1—C8—C7	28.40 (14)
O4ⁱⁱ—K1—C4—C5	24.49 (15)	K1ⁱ—K1—C8—C7	172.23 (13)
O3ⁱ—K1—C4—C5	−165.60 (13)	O1ⁱ—K1—C8—C3	15.9 (3)
C3—K1—C4—C5	−120.7 (2)	O2ⁱⁱ—K1—C8—C3	167.10 (13)
C6—K1—C4—C5	−29.02 (13)	O3—K1—C8—C3	−6.77 (14)
C8—K1—C4—C5	−90.37 (15)	O1—K1—C8—C3	54.39 (13)
K1ⁱ—K1—C4—C5	154.26 (13)	O4ⁱⁱ—K1—C8—C3	−119.77 (13)
O1ⁱ—K1—C4—C3	−133.94 (12)	O3ⁱ—K1—C8—C3	100.94 (13)
O2ⁱⁱ—K1—C4—C3	56.94 (14)	C4—K1—C8—C3	−32.06 (12)
O3—K1—C4—C3	−118.93 (14)	C5—K1—C8—C3	−66.32 (14)
O1—K1—C4—C3	−45.25 (12)	C6—K1—C8—C3	−98.48 (16)
O4ⁱⁱ—K1—C4—C3	145.22 (12)	K1ⁱ—K1—C8—C3	45.36 (14)
O3ⁱ—K1—C4—C3	−44.87 (15)	C5—C4—C9—C10	−108.5 (2)
C5—K1—C4—C3	120.7 (2)	C3—C4—C9—C10	72.1 (3)
C6—K1—C4—C3	91.71 (14)	K1—C4—C9—C10	−18.6 (2)
C8—K1—C4—C3	30.37 (11)	K1—O3—C10—O4	134.88 (18)
K1ⁱ—K1—C4—C3	−85.01 (12)	K1ⁱ—O3—C10—O4	42.3 (3)
O1ⁱ—K1—C4—C9	−13.62 (18)	K1—O3—C10—C9	−46.6 (3)
O2ⁱⁱ—K1—C4—C9	177.27 (14)	K1ⁱ—O3—C10—C9	−139.12 (17)
O3—K1—C4—C9	1.40 (14)	K1ⁱⁱⁱ—O4—C10—O3	−116.9 (2)
O1—K1—C4—C9	75.08 (15)	K1ⁱⁱⁱ—O4—C10—C9	64.4 (3)
O4ⁱⁱ—K1—C4—C9	−94.45 (16)	C4—C9—C10—O3	42.3 (3)
O3ⁱ—K1—C4—C9	75.46 (17)	C4—C9—C10—O4	−139.0 (2)
C5—K1—C4—C9	−118.9 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4′···O1^iv	1.01 (3)	2.57 (3)	3.248 (2)	125 (2)
O4—H4′···O2^iv	1.01 (3)	1.47 (3)	2.471 (2)	176 (3)
C2—H2A···O2^v	0.97	2.53	3.480 (3)	167

Symmetry codes: (iv) −x+1, −y+2, −z+1; (v) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[K(C₁₀H₉O₄)]
M_r	232.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.3365 (14), 6.7886 (11), 17.651 (3)
β (°)	92.543 (3)
V (Å³)	997.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.45 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.713, 0.864
No. of measured, independent and observed [I > 2σ(I)] reflections	8711, 1727, 1560
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.08
No. of reflections	1727
No. of parameters	139
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: SMART (Bruker, 2000), SAINT-Plus-NT (Bruker, 2001), SHELXTL-NT (Sheldrick, 2008), PLATON (Spek, 2003) and publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4'···O1ⁱ	1.01 (3)	2.57 (3)	3.248 (2)	125 (2)
O4—H4'···O2ⁱ	1.01 (3)	1.47 (3)	2.471 (2)	176 (3)
C2—H2A···O2ⁱⁱ	0.97	2.53	3.480 (3)	167

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1.

Acknowledgements

This work was supported by Consejo Nacional de Ciencia y Tecnología (CONACyT) under grant No. CIAM-59213.

References

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