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Acta Cryst. (2008). E64, m1626    [ doi:10.1107/S1600536808038889 ]

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

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

Abstract top

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-[pi] 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.

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—Carene 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).

Refinement top

Aromatic and methylene H atoms were positioned geometrically and constrained using the riding-model approximation [C-Haryl = 0.93 Å, Uiso(Haryl)= 1.2 Ueq(Caryl); C-Hmethylene = 0.97 Å, Uiso(Hmethylene) = 1.5 Ueq(Cmethylene)]. Atom H4', which is involved in a hydrogen-bonding interaction, was located by difference Fourier map, constrained using the riding-model approximation [Uiso(O4-H') = 1.5 Ueq(O4)] and the coordinates were refined freely.

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
[Figure 1] 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.
[Figure 2] Fig. 2. View of the one-dimensional coordination polymer chain running along to the b axis. Dashed and dotted lines indicate Caryl···K+ and O—H···O contacts, respectively. H atoms not involved in hydrogen-bonding have been omitted for clarity.
[Figure 3] 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
Mr = 232.27Dx = 1.546 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4833 reflections
a = 8.3365 (14) Åθ = 2.3–28.2°
b = 6.7886 (11) ŵ = 0.52 mm−1
c = 17.651 (3) ÅT = 293 K
β = 92.543 (3)°Rectangular, colourless
V = 997.9 (3) Å30.45 × 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 tube1560 reflections with I > 2σ(I)
graphiteRint = 0.039
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.713, Tmax = 0.864k = −8→8
8711 measured reflectionsl = −20→20
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.3852P]
where P = (Fo2 + 2Fc2)/3
1727 reflections(Δ/σ)max = 0.001
139 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
[K(C10H9O4)]V = 997.9 (3) Å3
Mr = 232.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.3365 (14) ŵ = 0.52 mm−1
b = 6.7886 (11) ÅT = 293 K
c = 17.651 (3) Å0.45 × 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)
Tmin = 0.713, Tmax = 0.864Rint = 0.039
8711 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101Δρmax = 0.21 e Å−3
S = 1.08Δρmin = −0.20 e Å−3
1727 reflectionsAbsolute structure: ?
139 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
K10.38073 (6)0.33470 (7)0.44502 (3)0.0455 (2)
O10.2998 (2)0.6914 (2)0.51210 (9)0.0487 (4)
O20.26242 (19)1.0124 (2)0.52043 (9)0.0449 (4)
O30.5412 (2)0.6608 (2)0.38998 (11)0.0569 (5)
O40.5243 (2)0.9834 (2)0.37776 (9)0.0471 (4)
H4'0.612 (4)0.991 (4)0.4186 (16)0.071*
C10.2360 (3)0.8431 (3)0.49014 (12)0.0350 (5)
C20.1154 (3)0.8450 (3)0.42353 (13)0.0449 (6)
H2A0.00910.86370.44260.054*
H2B0.13790.95720.39170.054*
C30.1135 (3)0.6626 (3)0.37550 (12)0.0362 (5)
C40.2223 (3)0.6353 (3)0.31858 (12)0.0378 (5)
C50.2138 (3)0.4620 (4)0.27695 (12)0.0458 (6)
H50.28590.44190.23890.055*
C60.1017 (3)0.3192 (4)0.29041 (14)0.0495 (6)
H60.09880.20390.26190.059*
C7−0.0052 (3)0.3471 (3)0.34570 (14)0.0498 (6)
H7−0.08160.25120.35490.060*
C80.0006 (3)0.5179 (3)0.38770 (13)0.0434 (6)
H8−0.07300.53650.42510.052*
C90.3453 (3)0.7892 (4)0.30161 (13)0.0497 (6)
H9A0.29190.91580.29630.060*
H9B0.39090.75830.25340.060*
C100.4803 (3)0.8065 (3)0.36163 (12)0.0393 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K10.0465 (3)0.0342 (3)0.0548 (3)0.0001 (2)−0.0082 (2)0.0024 (2)
O10.0540 (10)0.0367 (9)0.0542 (10)0.0060 (8)−0.0139 (8)−0.0016 (7)
O20.0498 (10)0.0346 (8)0.0497 (9)0.0011 (7)−0.0047 (7)−0.0062 (7)
O30.0503 (10)0.0450 (10)0.0735 (12)−0.0046 (8)−0.0172 (9)0.0114 (9)
O40.0466 (10)0.0432 (9)0.0508 (9)−0.0003 (7)−0.0053 (8)0.0004 (7)
C10.0315 (11)0.0362 (12)0.0379 (11)−0.0003 (9)0.0064 (9)0.0003 (9)
C20.0455 (13)0.0393 (13)0.0492 (13)0.0099 (10)−0.0077 (11)−0.0032 (10)
C30.0352 (11)0.0354 (11)0.0372 (11)0.0058 (9)−0.0090 (9)−0.0001 (9)
C40.0335 (11)0.0442 (12)0.0350 (11)0.0027 (9)−0.0077 (9)0.0037 (9)
C50.0416 (13)0.0596 (15)0.0357 (12)0.0124 (11)−0.0051 (10)−0.0076 (11)
C60.0541 (15)0.0428 (14)0.0498 (14)0.0022 (11)−0.0170 (12)−0.0106 (11)
C70.0502 (14)0.0435 (13)0.0542 (15)−0.0105 (11)−0.0139 (12)0.0053 (11)
C80.0387 (13)0.0508 (14)0.0405 (12)−0.0034 (10)−0.0013 (10)0.0031 (10)
C90.0455 (14)0.0583 (15)0.0446 (13)−0.0076 (12)−0.0052 (11)0.0133 (11)
C100.0339 (12)0.0448 (14)0.0395 (12)−0.0037 (10)0.0056 (9)0.0053 (10)
Geometric parameters (Å, °) top
K1—O1i2.7422 (17)O4—H4'1.00 (3)
K1—O2ii2.7654 (17)C1—C21.513 (3)
K1—O32.7837 (18)C2—C31.500 (3)
K1—O12.7912 (16)C2—H2A0.9700
K1—O4ii2.9419 (17)C2—H2B0.9700
K1—O3i2.956 (2)C3—C81.384 (3)
K1—C43.260 (2)C3—C41.396 (3)
K1—C53.334 (2)C4—C51.387 (3)
K1—C33.344 (2)C4—C91.503 (3)
K1—C63.508 (2)C5—C61.374 (3)
K1—C83.511 (2)C5—H50.9300
K1—K1i3.5235 (10)C6—C71.364 (4)
O1—C11.215 (2)C6—H60.9300
O1—K1i2.7422 (17)C7—C81.376 (3)
O2—C11.282 (2)C7—H70.9300
O2—K1iii2.7654 (17)C8—H80.9300
O3—C101.210 (3)C9—C101.515 (3)
O3—K1i2.956 (2)C9—H9A0.9700
O4—C101.284 (3)C9—H9B0.9700
O4—K1iii2.9420 (17)
O1i—K1—O2ii100.31 (5)C8—K1—K1i114.41 (4)
O1i—K1—O370.84 (5)C1—O1—K1i123.28 (14)
O2ii—K1—O3169.83 (5)C1—O1—K1135.31 (14)
O1i—K1—O1100.90 (5)K1i—O1—K179.10 (5)
O2ii—K1—O1112.58 (5)C1—O2—K1iii124.52 (13)
O3—K1—O165.62 (6)C10—O3—K1126.51 (15)
O1i—K1—O4ii69.61 (5)C10—O3—K1i117.98 (15)
O2ii—K1—O4ii73.33 (5)K1—O3—K1i75.67 (5)
O3—K1—O4ii107.07 (6)C10—O4—K1iii136.90 (14)
O1—K1—O4ii169.97 (5)C10—O4—H4'113.6 (16)
O1i—K1—O3i63.90 (5)K1iii—O4—H4'87.9 (16)
O2ii—K1—O3i66.52 (5)O1—C1—O2124.2 (2)
O3—K1—O3i104.32 (5)O1—C1—C2121.41 (19)
O1—K1—O3i67.66 (5)O2—C1—C2114.38 (18)
O4ii—K1—O3i109.28 (5)C3—C2—C1114.97 (18)
O1i—K1—C4126.04 (6)C3—C2—H2A108.5
O2ii—K1—C4133.04 (5)C1—C2—H2A108.5
O3—K1—C456.60 (5)C3—C2—H2B108.5
O1—K1—C469.46 (5)C1—C2—H2B108.5
O4ii—K1—C4113.01 (5)H2A—C2—H2B107.5
O3i—K1—C4137.12 (5)C8—C3—C4119.1 (2)
O1i—K1—C5128.62 (6)C8—C3—C2119.2 (2)
O2ii—K1—C5119.32 (6)C4—C3—C2121.7 (2)
O3—K1—C570.82 (6)C8—C3—K185.25 (13)
O1—K1—C593.06 (5)C4—C3—K174.46 (11)
O4ii—K1—C590.70 (5)C2—C3—K1110.62 (12)
O3i—K1—C5159.86 (6)C5—C4—C3118.3 (2)
C4—K1—C524.26 (6)C5—C4—C9120.2 (2)
O1i—K1—C3140.12 (5)C3—C4—C9121.5 (2)
O2ii—K1—C3117.21 (5)C5—C4—K180.87 (12)
O3—K1—C370.43 (5)C3—C4—K181.18 (12)
O1—K1—C353.74 (5)C9—C4—K1108.22 (13)
O4ii—K1—C3131.90 (5)C6—C5—C4121.7 (2)
O3i—K1—C3117.95 (5)C6—C5—K185.62 (14)
C4—K1—C324.36 (5)C4—C5—K174.87 (12)
C5—K1—C341.93 (5)C6—C5—H5119.1
O1i—K1—C6144.60 (6)C4—C5—H5119.1
O2ii—K1—C696.45 (6)K1—C5—H5110.3
O3—K1—C693.71 (6)C7—C6—C5119.8 (2)
O1—K1—C6101.04 (5)C7—C6—K182.60 (14)
O4ii—K1—C685.95 (5)C5—C6—K171.39 (13)
O3i—K1—C6151.19 (6)C7—C6—H6120.1
C4—K1—C641.56 (6)C5—C6—H6120.1
C5—K1—C623.00 (6)K1—C6—H6116.5
C3—K1—C647.66 (5)C6—C7—C8119.6 (2)
O1i—K1—C8162.86 (5)C6—C7—K175.30 (14)
O2ii—K1—C894.72 (5)C8—C7—K175.38 (13)
O3—K1—C893.40 (5)C6—C7—H7120.2
O1—K1—C865.34 (5)C8—C7—H7120.2
O4ii—K1—C8123.29 (5)K1—C7—H7120.2
O3i—K1—C8115.89 (5)C7—C8—C3121.5 (2)
C4—K1—C841.24 (5)C7—C8—K182.34 (14)
C5—K1—C846.86 (6)C3—C8—K171.62 (12)
C3—K1—C823.13 (5)C7—C8—H8119.3
C6—K1—C839.43 (6)C3—C8—H8119.3
O1i—K1—K1i51.07 (3)K1—C8—H8117.3
O2ii—K1—K1i116.32 (4)C4—C9—C10113.96 (18)
O3—K1—K1i54.37 (4)C4—C9—H9A108.8
O1—K1—K1i49.84 (4)C10—C9—H9A108.8
O4ii—K1—K1i120.59 (4)C4—C9—H9B108.8
O3i—K1—K1i49.95 (3)C10—C9—H9B108.8
C4—K1—K1i100.37 (4)H9A—C9—H9B107.7
C5—K1—K1i121.87 (5)O3—C10—O4124.2 (2)
C3—K1—K1i97.39 (4)O3—C10—C9120.7 (2)
C6—K1—K1i141.83 (5)O4—C10—C9115.0 (2)
O1i—K1—O1—C1126.9 (2)C3—K1—C4—C9120.3 (2)
O2ii—K1—O1—C1−127.0 (2)C6—K1—C4—C9−147.96 (19)
O3—K1—O1—C163.9 (2)C8—K1—C4—C9150.69 (19)
O4ii—K1—O1—C1108.4 (3)K1i—K1—C4—C935.31 (16)
O3i—K1—O1—C1−177.4 (2)C3—C4—C5—C60.2 (3)
C4—K1—O1—C12.3 (2)C9—C4—C5—C6−179.2 (2)
C5—K1—O1—C1−3.4 (2)K1—C4—C5—C674.9 (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—K1105.83 (18)
C8—K1—O1—C1−42.4 (2)O1i—K1—C5—C6142.02 (14)
K1i—K1—O1—C1126.9 (2)O2ii—K1—C5—C66.69 (16)
O1i—K1—O1—K1i0.0O3—K1—C5—C6−174.26 (16)
O2ii—K1—O1—K1i106.11 (5)O1—K1—C5—C6−111.41 (15)
O3—K1—O1—K1i−62.98 (5)O4ii—K1—C5—C677.89 (14)
O4ii—K1—O1—K1i−18.4 (3)O3i—K1—C5—C6−95.1 (2)
O3i—K1—O1—K1i55.70 (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—C4131.23 (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—C413.13 (14)
O1—K1—O3—C10−57.54 (19)O4ii—K1—C5—C4−157.57 (14)
O4ii—K1—O3—C10129.80 (19)O3i—K1—C5—C429.4 (3)
O3i—K1—O3—C10−114.4 (2)C3—K1—C5—C432.04 (12)
C4—K1—O3—C1023.11 (18)C6—K1—C5—C4124.5 (2)
C5—K1—O3—C1045.16 (19)C8—K1—C5—C464.62 (13)
C3—K1—O3—C100.58 (19)K1i—K1—C5—C4−30.21 (15)
C6—K1—O3—C1042.9 (2)C4—C5—C6—C70.3 (3)
C8—K1—O3—C103.4 (2)K1—C5—C6—C769.5 (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—C7178.97 (13)
O2ii—K1—O3—K1i−25.1 (3)O2ii—K1—C6—C760.94 (15)
O1—K1—O3—K1i56.88 (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—K1i0.0O4ii—K1—C6—C7133.63 (15)
C4—K1—O3—K1i137.53 (7)O3i—K1—C6—C79.7 (2)
C5—K1—O3—K1i159.58 (6)C4—K1—C6—C7−94.26 (16)
C3—K1—O3—K1i115.00 (6)C5—K1—C6—C7−124.9 (2)
C6—K1—O3—K1i157.33 (5)C3—K1—C6—C7−60.36 (14)
C8—K1—O3—K1i117.82 (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—C2138.33 (17)O2ii—K1—C6—C5−174.13 (14)
K1—O1—C1—C228.3 (3)O3—K1—C6—C55.43 (15)
K1iii—O2—C1—O1120.5 (2)O1—K1—C6—C571.30 (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—C5134.65 (15)
O2—C1—C2—C3165.1 (2)C4—K1—C6—C530.67 (13)
C1—C2—C3—C897.3 (2)C3—K1—C6—C564.57 (14)
C1—C2—C3—C4−83.0 (3)C8—K1—C6—C596.28 (16)
C1—C2—C3—K11.1 (2)K1i—K1—C6—C535.89 (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—C863.3 (2)
O3—K1—C3—C8172.82 (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—C877.11 (15)O2ii—K1—C7—C6−119.40 (15)
O3i—K1—C3—C8−90.94 (13)O3—K1—C7—C663.61 (15)
C4—K1—C3—C8121.97 (19)O1—K1—C7—C6127.72 (15)
C5—K1—C3—C890.07 (15)O4ii—K1—C7—C6−47.38 (15)
C6—K1—C3—C858.20 (14)O3i—K1—C7—C6−173.97 (13)
K1i—K1—C3—C8−139.20 (13)C4—K1—C7—C663.69 (15)
O1i—K1—C3—C465.24 (15)C5—K1—C7—C630.06 (14)
O2ii—K1—C3—C4−136.46 (12)C3—K1—C7—C697.57 (17)
O3—K1—C3—C450.85 (12)C8—K1—C7—C6126.6 (2)
O1—K1—C3—C4124.43 (14)K1i—K1—C7—C6116.29 (14)
O4ii—K1—C3—C4−44.86 (15)O1i—K1—C7—C8−129.2 (2)
O3i—K1—C3—C4147.09 (12)O2ii—K1—C7—C8114.02 (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—C81.15 (14)
C8—K1—C3—C4−121.97 (19)O4ii—K1—C7—C8−173.96 (14)
K1i—K1—C3—C498.82 (12)O3i—K1—C7—C859.46 (16)
O1i—K1—C3—C2−53.34 (19)C4—K1—C7—C8−62.89 (14)
O2ii—K1—C3—C2104.95 (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—C25.85 (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—C228.50 (17)C6—C7—C8—C3−0.4 (3)
C4—K1—C3—C2−118.6 (2)K1—C7—C8—C362.90 (19)
C5—K1—C3—C2−150.48 (19)C6—C7—C8—K1−63.3 (2)
C6—K1—C3—C2177.65 (19)C4—C3—C8—C70.9 (3)
C8—K1—C3—C2119.4 (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—K169.28 (17)
C2—C3—C4—C5179.52 (19)C2—C3—C8—K1−111.00 (18)
K1—C3—C4—C574.57 (17)O1i—K1—C8—C7142.7 (2)
C8—C3—C4—C9178.6 (2)O2ii—K1—C8—C7−66.03 (14)
C2—C3—C4—C9−1.1 (3)O3—K1—C8—C7120.10 (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—C77.10 (16)
C2—C3—C4—K1104.94 (18)O3i—K1—C8—C7−132.18 (14)
O1i—K1—C4—C5105.32 (14)C4—K1—C8—C794.82 (16)
O2ii—K1—C4—C5−63.79 (16)C5—K1—C8—C760.55 (15)
O3—K1—C4—C5120.34 (15)C3—K1—C8—C7126.9 (2)
O1—K1—C4—C5−165.98 (15)C6—K1—C8—C728.40 (14)
O4ii—K1—C4—C524.49 (15)K1i—K1—C8—C7172.23 (13)
O3i—K1—C4—C5−165.60 (13)O1i—K1—C8—C315.9 (3)
C3—K1—C4—C5−120.7 (2)O2ii—K1—C8—C3167.10 (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—C354.39 (13)
K1i—K1—C4—C5154.26 (13)O4ii—K1—C8—C3−119.77 (13)
O1i—K1—C4—C3−133.94 (12)O3i—K1—C8—C3100.94 (13)
O2ii—K1—C4—C356.94 (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—C3145.22 (12)K1i—K1—C8—C345.36 (14)
O3i—K1—C4—C3−44.87 (15)C5—C4—C9—C10−108.5 (2)
C5—K1—C4—C3120.7 (2)C3—C4—C9—C1072.1 (3)
C6—K1—C4—C391.71 (14)K1—C4—C9—C10−18.6 (2)
C8—K1—C4—C330.37 (11)K1—O3—C10—O4134.88 (18)
K1i—K1—C4—C3−85.01 (12)K1i—O3—C10—O442.3 (3)
O1i—K1—C4—C9−13.62 (18)K1—O3—C10—C9−46.6 (3)
O2ii—K1—C4—C9177.27 (14)K1i—O3—C10—C9−139.12 (17)
O3—K1—C4—C91.40 (14)K1iii—O4—C10—O3−116.9 (2)
O1—K1—C4—C975.08 (15)K1iii—O4—C10—C964.4 (3)
O4ii—K1—C4—C9−94.45 (16)C4—C9—C10—O342.3 (3)
O3i—K1—C4—C975.46 (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, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4'···O1iv1.01 (3)2.57 (3)3.248 (2)125 (2)
O4—H4'···O2iv1.01 (3)1.47 (3)2.471 (2)176 (3)
C2—H2A···O2v0.972.533.480 (3)167
Symmetry codes: (iv) −x+1, −y+2, −z+1; (v) −x, −y+2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4'···O1i1.01 (3)2.57 (3)3.248 (2)125 (2)
O4—H4'···O2i1.01 (3)1.47 (3)2.471 (2)176 (3)
C2—H2A···O2ii0.972.533.480 (3)167
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1.
Acknowledgements top

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

references
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