New coordination modes in potassium edta salts: K₂[H₂edta]·2H₂O, K₃[Hedta]·2H₂O and K₄[edta]·3.92H₂O

Three potassium edta (edta is ethyl­enediamine­tetra­acetic acid, H₄Y) salts which have different degrees of ionization of the edta anion, namely dipotassium 2-({2-[bis­(carboxyl­atometh­yl)aza­nium­yl]eth­yl}(carboxyl­atometh­yl)aza­nium­yl)acetate di­hydrate, 2K⁺·C₁₀H₁₄N₂O₈²⁻·2H₂O, (I), tripotassium 2,2′-({2-[bis(carboxylatomethyl)amino]ethyl}ammonio)diacetate dihydrate, 3K⁺·C₁₀H₁₃N₂O₈³⁻·2H₂O, (II), and tetra­potassium 2,2′,2′′,2′′′-(ethane-1,2-diyldinitrilo)­tetra­ace­tate 3.92-hydrate, 4K⁺·C₁₀H₁₂N₂O₈⁴⁻·3.92H₂O, (III), were ob­tained in crystalline form from water solutions after mixing edta with potassium hydroxide in different molar ratios. In (II), a new mode of coordination of the edta anion to the metal is observed. The HY³⁻ anion contains one deprotonated N atom coordinated to K⁺ and the second N atom is involved in intra­molecular bifurcated N—H...O and N—H...N hydrogen bonds. The overall conformation of the HY³⁻ anions is very similar to that of the Y⁴⁻ anions in (III), although a slightly different spatial arrangement of the –CH₂COO⁻ groups in relation to (III) is observed, whereas the H₂Y²⁻ anions in (I) adopt a distinctly different geometry. The preferred synclinal conformation of the –NCH₂CH₂N– moiety was found for all edta anions. In all three crystals, the anions and water mol­ecules are arranged in three-dimensional networks linked via O—H...O and C—H...O [and N—H...O in (I) and (II)] hydrogen bonds. K...O inter­actions also contribute to the three-dimensional polymeric architecture of the salts.

S1. Comment

In the literature the most common form of edta [edta = ethylenediamine tetraacetic acid = 2,2',2",2"'-(ethane-1,2-diyldinitrilo)tetraacetic acid] in crystals is the tetra-anion Y^4- (Y^4- = [C₁₀H₁₂N₂O₈]^4-). Another anionic form of edta is H₂Y^2- reported in salts of Na, K and Rb (Font-Bardia et al., 1993; Cotrait, 1969, 1970). Therefore, it seemed an attractive idea to obtain and structurally characterize crystalline potassium edta salts, epecially the tripotassium edta salt, (II), which is an example of a new coordination mode of this edta anion to a metal centre, tetrapotassium edta (III) - analogous to the Na₄Y.5H₂O salt (Font-Bardia et al., 1993). Potassium edta salts are used as anticoagulants for haematologic examinations of human and animal blood (Balakrishnan et al., 2006; Hekimsoy et al., 2004; Vatn et al., 2000; Olsen et al., 2001; Sanchez-Migallon Guzman et al., 2008). In addition, potassium edta salts have applications as chelating agents in cosmetics (Lanigan & Yamarik, 2002).

The strategies for preparing the potassium edta salts reported here, (I), (II) and (III), result from the occurrence of acid–base equilibria in aqueous solution between edta anions in different ionization states. The acidity of solutions plays a crucial role in controlling the particular forms of the edta anions, H₃Y^-, H₂Y^2-, HY^3- and Y^4- (Harris, 1999), as follows. The H₃Y^- anion is dominant in aqueous solutions at pH values around 2.5 and its conjugate acid – the H₄Y zwitterion – at pH ~1.8. In the pH range of 2.7–6.1 [pK_a{H₂Y^2-} = 2.69; pK_a{HY^3-} = 6.13] the equilibrium shifts towards the H₂Y^2- ion. The HY^3- ion dominates in aqueous solutions in the pH range 6.1–10.4 (pK_a{Y^4-} = 10.37) whereas the Y^4- anion dominates at pH above 10.4.

In contrast to the coordination modes in the salts (I), (II), (III), in the majority of compounds that contain edta anions and potassium cations the usual coordination of edta to K⁺ is via one carboxylate group in a monodentate or bidentate way. The literature provides many examples of such compounds, among which the most typical include: the acetate O atom acting as a linker between two metal atoms, e.g. between two K cations, as in K₄[Co(H₂O)₆][Co(C₁₀H₁₂N₂O₈)]₂[Mo₈O₂₆].6H₂O (Lee et al., 2002); or between one K cation and another metal such as Fe, Sb, Mo (Solans et al., 1984; Ilyukhin & Petrosyants, 2001; Kneale & Geddes, 1975); or between one K cation and a lanthanoid cation, as in K[Ho(C₁₀H₁₂N₂O₈)(H₂O)₃].2H₂O (Sakagami et al., 1999). Furthermore, the carboxylate O atom of edta can bridge three metal atoms, shown in the following examples: three K cations, as in K₂[Ga(C₁₀H₁₂O₈N₂)(OH).6H₂O (Ilyukhin & Petrosyants, 2001); two K cations and another cation such as a lanthanoid, as in K[Yb(C₁₀H₁₂N₂O₈)(H₂O).5H₂O (Sakagami et al., 1997); or one K cation and two transition metal centres, as in K[Mo₂(C₁₂H₁₅N₂O₁₀)(OH)₂ (Kneale & Geddes, 1975).

The present paper reports the structures of three potassium edta salts, K₂[C₁₀H₁₄N₂O₈].2H₂O, (I), K₃[C₁₀H₁₃N₂O₈]. 2H₂O, (II), and K₄[C₁₀H₁₂N₂O₈].3.93H₂O, (III) (Fig. 1). The geometries of the anions in (I)–(III) are described and compared with those in the dirubidium, di- and tetrasodium edta salts. In addition, the coordination modes of the edta anions to K⁺ ions and the arrangements in the crystal lattices are discussed.

Compound (II) contains one HY^3- anion, three K⁺ ions and two water molecules of hydration, where the anion is composed of four acetate CH₂COO^- arms linked to a NCH₂CH₂NH⁺ fragment which adopts a gauche conformation; a novel coordination mode is observed. The HY^3- ion coordinates to the cation (K1) via one deprotonated N atom (N1) and three acetate O atoms (O11, O21, O32), while the second N atom (N2) is involved in the intramolecular bifurcated N—H···O and N—H···N hydrogen bonds (Figs. 1b, 2a, Tables 2 and 6). Furthermore, in the coordination polyhedron of K1 two symmetry-related anions are also present and bonded in a bidentate mode (via O32^vi and O42^vi) (all symmetry codes are given in Table 6) forming an eight-membered ring, and in a monodentate (via O41^vii) fashion (Fig. 2b, Table 6). The (OOCCH₂)₂NCH₂CH₂NH⁺(CH₂COO)₂ unit observed here can also be distinguished in the structure of a fully esterified form of edta acid with the proton added to one of the nitrogen atoms: (C₁₄H₂₅N₂O₈)₂[W₆Cl₁₄] (Adams et al., 1993), where intramolecular N—H···N and N—H···O hydrogen bonds occur, but the coordination to the metal atom is not observed. In the case of the atom K2, the six-coordination sphere is formed by three HY^3- anions and one water molecule, O2W (Fig. 2c, Table 6). The anion coordinates to K2 in a bidentate manner via O31 and O32, and is involved in coordination to K2^viii in a monodentate way via O22 as well as interacting with K2^vi via two oxygen O21 and O42 (making an 11-membered chelate ring) (Fig. 2d, Table 6). The K3 is surrounded by five edta anions coordinated via O atoms in a monodentate way and by two water molecules.

In the crystal structure of (II), O—H···O hydrogen bonds are present, where water molecules act as donors and carboxylate O atoms as acceptors (Table 2). Weak hydrogen bonds of the C—H···O type, where the acetate O atoms participate, also contribute to the structure. The HY^3- anions, water molecules and K cations are arranged in layers parallel to (100) (Fig. 3a). The interaction between acetate O atoms, water molecules and K cations results in a three-dimensional network.

The asymmetric unit of compound (III) comprises two Y^4- anions [denoted (IIIa) and (IIIb)], eight potassium cations and water molecules (Fig. 1c). The overall conformations of the (IIIa) and (IIIb) anions are similar although the spatial arrangements of their acetate arms are not quite the same (Fig. 4). The overall conformations of anions in (III) are comparable with those of the corresponding Y^4- anion in Na₄[edta].5H₂O (Font-Bardia et al., 1993) and the HY^3- ion in (II), although the spatial location of analogous acetate arms are not exactly the same. Both edta anions in compound (IIIa) chelate K⁺ via six ligating atoms (two N and four carboxylate O atoms) which results in the formation of five-membered rings at both K1 and K2, similar to the complexes of Y^4- ions with many metals: for example NH₄[Co(C₁₀H₁₂N₂O₈)].2H₂O (Weakliem & Hoard, 1959), [(H₂O)₄Mn(C₁₀H₁₂N₂O₈)Cu]_n.2nH₂O (Solans et al., 1983), [Ti(C₁₀H₁₂N₂O₈)].2H₂O (Fackler et al., 1985).

Each of four chelate rings formed by the acetate arms with K1 adopt the δ conformation (δδδδ) (Corey & Bailar, 1959; Beattie, 1971; Lee, 1972). In the case of coordination at K2 (coordination number = 8) (Fig. 5b, Table 6) the {K2,O11B,C11B,C12B,N1B} ring adopts the λ conformation, the {K2,O21B,C21B,C22B,N1B} and {K2,O32B,C31B,C32B,N2B} rings are in δ conformation, whereas the {K2,O42B,C41B,C42B,N2B} ring adopts a near-envelope conformation; four atoms, O42B, C41B, C42B, N2B, are nearly in the same plane (Table 5).

The eight-coordination sphere of K1 is made up of two type-(IIIa) anions and one water molecule (Fig. 5a, Table 6). The (IIIa) anion chelates K1 forming a cage structure and coordinates to K1^xii in a monodentate way via O11A. The seven-coordinate sphere of K3 is built up from three Y^4- anions and two water molecules (Fig. 5c, Table 6). The (IIIa) anion is bonded to K3^xvi through a bidentate –CH₂COO^- group and coordinates to K3^xv in a monodentate manner via O41A. The (IIIb) anion coordinates to K3 in a bidentate manner through O22B and O42B atoms of –CH₂COO^- groups bonded to two different N atoms which results in the formation of an 11-membered ring, as in (II) and in Rb₂[H₂edta].2H₂O (Cotrait, 1970). Such an 11-membered ring can be distinguished at K5 as well (Table 6). The environment of K4 is made up of three Y^4- ions and two water molecules (Table 6). The coordination spheres of the K6–K8 cations are built by anions linked to K⁺ ions through monodentate carboxylate groups and water molecules.

The shortest K···K distances are in the range 3.6949 (9)–4.4803 (15) Å, where adjacent K⁺ cations are bridged by edta anions via O atoms giving a three-dimensional polymeric structure. Compound (III) also contains numerous O—H···O hydrogen bonds in which the O atoms of anions and water molecules are involved (Table 3). Adjacent anions and water molecules form layers while K cations act as linkers between such layers. The Y^4- anions, K⁺ cations and water molecules are arranged in ribbons extending along the [001] direction (Fig. 3b). Weak C—H···O hydrogen bonds are also observed between neighbouring anions and between anions and water molecules.

The dipotassium edta salt (I) was initially studied by Cotrait (1969) who used photographic methods at room temperature. This salt contains an H₂Y^2- anion, two potassium cations and two water molecules. In the H₂Y^2- anion the NH⁺CH₂CH₂NH⁺ fragment adopts a gauche conformation. Atoms N1 and N2 are both involved in the intramolecular hydrogen bonds, bi- and trifurcated, respectively (Table 1, Fig. 1a). This anion is also found in Rb₂[H₂edta].2H₂O (Cotrait, 1970) and Na₂[H₂edta].2H₂O (Font-Bardia et al., 1993) salts. The H₂Y^2- ion in (I) has a different overall conformation in relation to the relevant anions in the dirubidium and disodium edta salts (Cotrait, 1970; Font-Bardia et al., 1993) in which NCH₂CH₂N units adopt an antiperiplanar conformation and the acetate arms have a different geometry. However, the anion in (I) has similar overall geometry to the Y^4- ligand in complexes such as Li[FeY].3H₂O, NH₄[CoY].2H₂O, [MgY(H₂O)][Mg(H₂O)₆].2H₂O, Ca₂Y(H₂O)₃].4H₂O (Lind et al., 1964; Weakliem & Hoard, 1959; Pozhidaev et al., 1973; Barnett & Uchtman, 1979). Such similarity may result from the occurrence of intramolecular hydrogen bonds of the N—H···O type in (I) (mentioned above).

In the coordination polyhedron of atom K1 in (I), the edta anion acts as a tridentate ligand (Fig. 6). The coordination sphere of K1 is made up of four different edta anions and one water molecule, O1W. The coordination is via two O atoms (O11 and O21) derived from two different CH₂COO^- groups joined to the N1 atom and via O32 atom. The symmetry-related anions which occupy positions in the coordination sphere of the K1 cation are bonded to K1 in a monodentate fashion via O12ⁱ, O22ⁱⁱ, O31ⁱⁱⁱ atoms (Table 6, Fig. 6). Similarly to K1 the coordination sphere of the K2 cation is made up of four H₂Y^2- anions and one water molecule (O2W) as well. However, two anions chelate K2 by bidentate carboxylate groups (O21, O22 and O41^v, O42^v) while the other two are bonded in a monodentate manner through O11ⁱⁱ and O31^iv (Table 6).

As with compounds (II) and (III), compound (I) has a three-dimensional polymeric structure in which potassium cations are bridged by acetate O atoms. Additionally the K···O interactions result in tetrameric, centrosymmetric motifs where the shortest K···K distances are in the range 3.6987 (10)–4.6515 (11) Å (Fig. 6, Table 6).

The crystal structure of (I) is stabilized by a three-dimensional network of intermolecular hydrogen bonds of O—H···O and C—H···O types (Table 1). As in (II) and (III), a layered architecture built of anions, water molecules and K⁺ cations is observed.

Consideration of the geometries of the anions in (I)–(III) leads to the following conclusions. The preferred conformation of the NCH₂CH₂N unit of anions in (I)–(III) is synclinal. The overall geometry of the edta anions in potassium salts can be classified into two basic groups. The first one is formed by anions in (II) and (III), the overall conformations of which are very similar with small differences in the spatial arrangement of the corresponding CH₂COO^- groups (Fig. 7), whereas a distinctly different conformation is adopted by the anion in (I) (Fig. 7), classified into the second group of edta geometry. The overall conformation of H₂Y^2- in (I) is similar to that in the complexes noted above, in which the acetate arms of Y^4- are involved in five-membered rings with a metal atom. The values of C—N_protonated bond lengths in (I) are similar to values in (II) and the relevant values of C—N_unprotonated bond lengths in (II) and (III) are also similar (Table 5).

Related literature

For related literature, see: Lis, 1975

S2. Experimental

The three salts were obtained by reactions of free edta with potassium hydroxide and crystallized from water solutions under a gentle stream of nitrogen. All operations were performed at room temperature. All compounds used for syntheses were obtained commercially and not further purified. The strategies for preparing salts (I)–(III) are based on slow crystallization from water solutions prepared by mixing edta acid and potassium hydroxide in the different molar ratios. Contrary to our procedures of preparation, both the corresponding di- and tetrasodium edta salts were obtained in the reactions between edta acid and disodium carbonate in aqueous solutions at controlled pH (Font-Bardia et al., 1993).

For the synthesis of (I), free edta (0.16 g, 0.55 mmol) and potassium hydroxide (0.064 g, 1.1 mmol) were mixed at the molar ratio of 1:2. A small amount of distilled water (about 5 ml) was added, and the mixture was stirred for about 15 min. The solution (pH value ca. 4–4.5) was filtered to remove insoluble crystals of edta acid, and the filtered solution was allowed to evaporate. The crystals have the same cell dimensions as those reported by Cotrait (1969).

Compound (I) was also obtained as a result of mixing edta with potassium hydroxide at the molar ratio of 1:3. The KOH (2.318 g, 0.04139 mol) was dissolved in distilled water (about 7 ml) and the edta (4.031 g, 0.01379 mol) added to this solution. This mixture was stirred at room temperature until a clear solution was obtained. The crystallization was carried out by evaporation as in the case of the previous procedure. The crystals in the form of long plates were obtained from solution with a pH of about 6.5–7.

For the synthesis of (II), potassium hydroxide (0.3832 g, 6.843 mmol) was dissolved in a minimal amount of distilled water. The edta (0.5003 g, 1.712 mmol) was added to give a molar ratio of 1:4 with continuous stirring to give a clear solution with a pH of about 10.5. The solution was allowed to evaporate to give colourless crystals in the form of plates during 1 d.

The crystalline salt (III) was obtained as a result of the reaction of edta with potassium hydroxide mixed at the molar ratio of 1:5. Preparative procedures were performed as in the case of salt (II). KOH (1.85 g, 0.0334 mol) was dissolved in a minimal amount of distilled water. The edta (1.928 g, 6.597 mmol) was added (the pH was about 13). The solution was evaporated under a nitrogen stream. The crystals appeared in the form of blocks.

S3. Refinement

In the case of the H₂Y^2-, (I), and HY^3-, (II), anions the H atoms of N—H groups were localized in the difference Fourier maps but introduced in positions calculated from geometry, with N—H distances of 0.93 Å and U_iso(H) = 1.2U_eq(N). The methylene H atoms in (I)–(III) were treated as riding atoms in geometrically idealized positions with C—H distances of 0.99 Å and U_iso(H) = 1.2U_eq(C).

In (III) partial disorder is present in the case of the acetate group (O31B, O32B, C31B), certain water molecules (O7W, O8W, O9W) and the K7 cation. Disorder of the carboxylate oxygen atoms was identified from the difference Fourier map peaks close to O31B and O32B with distances of approximately 0.52 and 0.42 Å, respectively. Because of the fact that both O atoms and the C31B atom belong to the same carboxylate group, the disorder was modelled for each of them between two positions, with occupancies of 0.793 (11) and 0.207 (11); the minor-occupancy components were refined isotropically.

Additionally in the difference Fourier map two peaks were localized and interpreted as disorder of the oxygen atoms of water molecules. Peaks were at distances of 0.61 and 0.74 Å from O7W and O9W atoms, respectively, and were introduced as O71W and O91W. The O7W atom was modelled as disordered in two positions with occupancies of 0.892 (10) and 0.108 (10). The sum of occupation factors for O9W and O91W atoms was smaller than unity. Therefore the disorder was modelled with occupancies of 0.282 (14) and 0.298 (14) for O9W and O91W, respectively. The K7 cation was also disordered in two positions with occupancies of 0.947 (8) and 0.053 (8). The O8W atom was located in the difference Fourier map and refined with an occupancy of 0.267 (2).

The H atoms which belong to water molecules (O7W, O8W and O9W) were localized in the difference Fourier map and introduced with distance constraints for the O—H and H—H distances of 0.84 (2) and 1.41 (2) Å, respectively. In the last stages of refinement these H atoms were permitted to ride at the positions previously established, with U_iso(H) = 1.5U_eq(O), giving O—H distances in the range 0.83–0.87 Å.

Computing details

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures

	Fig. 1. The asymmetric part of the unit cell in crystal of (a) K2[H2Y].2H2O, (I), (b) K3[HY].2H2O, (II), and (c) K4[Y].3.92H2O, (III). For (I) and (II), the N—H···O and for (I) N—H···N intramolecular hydrogen bonds are shown by dashed lines. Displacement ellipsoids are shown at the 30% probability level. The disordered atoms (O31C, O32C, O7W and K71) in (III) have been removed for clarity.
	Fig. 2. (a) The new coordination mode of the HY^3- anion to K^+ in (II); only ligating O atoms from symmetry-related anions in the coordination sphere of K1 are shown for clarity. (b) The coordination environment of K1. (c) The coordination sphere of the K2 cation in (II). (d) The environment of the HY^3- anion. [Symmetry codes: (vi) -x + 1, -y + 2, -z + 1; (vii) x - 1, y, z; (viii) x, y, z + 1; (x) x, y + 1, z; (xi) -x, -y + 2, -z.]
	Fig. 3. Packing diagrams: (a) for (II) showing layers parallel to the (010) plane; (b) for (III) showing ribbons built up from the anions, water molecules and K^+ cations extending along the [001] direction. Water molecules in cavities (O9W and O91W) and disordered atoms (O31C, O32C, O7W and K71) in (III) have been omitted for clarity.
	Fig. 4. The molecular structure of two crystallographically independent Y^4- anions in (III) (left). A comparison of the geometry of respective anions (right). The reference points are distinguished by atoms N1, C1, C2 and N2. Disordered atoms O31C and O32C have been removed for clarity.
	Fig. 5. The coordination environment of (a) the K1, (b) the K2 and (c) the K3 cation in (III). Disordered atoms O31C and O32C in (III) have been omitted for clarity. [Symmetry codes: (xii) x + 1/2, -y + 1/2, -z + 1; (xiii) -x + 1/2, y + 1/2, -z + 3/2; (xv) -x + 1, y, -z + 3/2; (xvi) x, -y + 1, z + 1/2.]
	Fig. 6. The coordination sphere of K1 in (I) (top). The tetrameric structure built by four adjacent K^+ cations in (I) (bottom). [Symmetry codes: (i) x + 1/2, -y + 3/2, z + 1/2; (ii) -x + 1, -y + 1, -z + 1; (iii) x + 1/2, -y + 3/2, z - 1/2.]
	Fig. 7. The molecular structures for the H2Y^2- anion in (I) and the HY^3- anion in (II) (top). A comparison of the geometry of respective anions (bottom). The reference points are distinguished by atoms N1, C1, C2 and N2.

(I) dipotassium 2-({2-[bis(carboxylatomethyl)azaniumyl]ethyl}(carboxylatomethyl)azaniumyl)acetate dihydrate

Crystal data

2K^+·C10H14N2O8^2^−·2H2O	F(000) = 840
Mr = 404.46	Dx = 1.695 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 16880 reflections
a = 8.869 (3) Å	θ = 4.3–38.6°
b = 18.653 (5) Å	µ = 0.65 mm^−1
c = 9.613 (3) Å	T = 110 K
β = 94.56 (3)°	Block, colourless
V = 1585.3 (8) Å^3	0.31 × 0.12 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur PX KM-4-CCD diffractometer	8782 independent reflections
Radiation source: fine-focus sealed tube	6388 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ϕ and ω scans	θmax = 38.6°, θmin = 4.3°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	h = −14→15
Tmin = 0.879, Tmax = 0.959	k = −32→32
30091 measured reflections	l = −12→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.032P)^2] where P = (Fo^2 + 2Fc^2)/3
8782 reflections	(Δ/σ)max = 0.002
217 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
K1	0.57928 (2)	0.655529 (9)	0.589830 (18)	0.01163 (4)
K2	0.44431 (2)	0.432278 (11)	0.75620 (2)	0.01597 (4)
O11	0.39078 (7)	0.67095 (3)	0.36045 (6)	0.01317 (11)
O12	0.27573 (7)	0.73966 (3)	0.19097 (6)	0.01392 (11)
O21	0.32992 (7)	0.55632 (3)	0.62596 (6)	0.01241 (11)
O22	0.25824 (8)	0.46147 (3)	0.49239 (7)	0.01610 (12)
O31	0.25343 (7)	0.81123 (3)	0.82693 (6)	0.01322 (11)
O32	0.32438 (7)	0.71948 (3)	0.69470 (6)	0.01323 (11)
O41	0.25913 (8)	0.53198 (4)	1.13856 (6)	0.01757 (13)
O42	0.39042 (8)	0.58474 (5)	0.97715 (7)	0.02619 (17)
N1	0.13838 (7)	0.64856 (3)	0.48919 (7)	0.00789 (11)
H1	0.2286	0.6562	0.5433	0.009*
N2	0.14064 (8)	0.62336 (3)	0.81555 (7)	0.00866 (11)
H2	0.2295	0.6127	0.7746	0.010*
C1	0.01165 (9)	0.66241 (4)	0.58071 (8)	0.00948 (13)
H1A	−0.0857	0.6568	0.5238	0.011*
H1B	0.0184	0.7128	0.6132	0.011*
C2	0.01047 (9)	0.61382 (4)	0.70708 (8)	0.00990 (13)
H2A	−0.0848	0.6220	0.7518	0.012*
H2B	0.0098	0.5634	0.6747	0.012*
C11	0.27998 (9)	0.70379 (4)	0.30110 (8)	0.00979 (13)
C12	0.13176 (9)	0.70201 (4)	0.37285 (8)	0.01051 (13)
H12A	0.1115	0.7502	0.4103	0.013*
H12B	0.0474	0.6896	0.3034	0.013*
C21	0.25256 (9)	0.52601 (4)	0.52646 (8)	0.01022 (13)
C22	0.14114 (9)	0.57280 (4)	0.43680 (8)	0.00986 (13)
H22A	0.1700	0.5728	0.3394	0.012*
H22B	0.0384	0.5520	0.4369	0.012*
C31	0.25209 (9)	0.74667 (4)	0.78901 (8)	0.01004 (13)
C32	0.15280 (9)	0.69829 (4)	0.87130 (8)	0.01054 (13)
H32A	0.1949	0.6967	0.9698	0.013*
H32B	0.0502	0.7194	0.8696	0.013*
C41	0.27168 (10)	0.56253 (5)	1.02329 (8)	0.01405 (15)
C42	0.12428 (9)	0.57083 (4)	0.93155 (8)	0.01151 (14)
H42A	0.0937	0.5237	0.8914	0.014*
H42B	0.0436	0.5874	0.9894	0.014*
O1W	0.65494 (8)	0.60818 (4)	0.85551 (7)	0.01817 (13)
H11W	0.6829	0.5647	0.8440	0.027*
H12W	0.5653	0.6051	0.8824	0.027*
O2W	0.17125 (8)	0.40097 (4)	0.88160 (8)	0.02328 (15)
H22W	0.1813	0.3675	0.8214	0.035*
H21W	0.2139	0.3841	0.9580	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.01054 (7)	0.01151 (7)	0.01245 (7)	0.00030 (6)	−0.00140 (5)	−0.00081 (6)
K2	0.01416 (8)	0.01864 (9)	0.01488 (8)	0.00442 (6)	−0.00024 (6)	0.00273 (7)
O11	0.0086 (2)	0.0168 (3)	0.0139 (3)	0.0011 (2)	−0.0002 (2)	0.0026 (2)
O12	0.0147 (3)	0.0154 (3)	0.0119 (3)	0.0000 (2)	0.0028 (2)	0.0048 (2)
O21	0.0126 (3)	0.0112 (3)	0.0130 (3)	0.0013 (2)	−0.0013 (2)	−0.0014 (2)
O22	0.0209 (3)	0.0084 (3)	0.0185 (3)	0.0024 (2)	−0.0009 (2)	−0.0019 (2)
O31	0.0141 (3)	0.0086 (2)	0.0167 (3)	−0.0009 (2)	−0.0007 (2)	−0.0018 (2)
O32	0.0127 (3)	0.0135 (3)	0.0138 (3)	−0.0025 (2)	0.0029 (2)	−0.0032 (2)
O41	0.0248 (3)	0.0180 (3)	0.0099 (2)	0.0059 (3)	0.0015 (2)	0.0038 (2)
O42	0.0125 (3)	0.0469 (5)	0.0193 (3)	0.0052 (3)	0.0028 (3)	0.0119 (3)
N1	0.0075 (3)	0.0080 (3)	0.0082 (2)	0.0004 (2)	0.0010 (2)	0.0007 (2)
N2	0.0093 (3)	0.0083 (3)	0.0084 (3)	0.0000 (2)	0.0008 (2)	0.0003 (2)
C1	0.0079 (3)	0.0117 (3)	0.0090 (3)	0.0014 (2)	0.0011 (2)	0.0007 (2)
C2	0.0091 (3)	0.0121 (3)	0.0085 (3)	−0.0020 (2)	0.0004 (3)	0.0002 (2)
C11	0.0096 (3)	0.0096 (3)	0.0101 (3)	−0.0014 (2)	0.0009 (3)	−0.0008 (2)
C12	0.0102 (3)	0.0110 (3)	0.0105 (3)	0.0015 (3)	0.0020 (3)	0.0039 (3)
C21	0.0103 (3)	0.0095 (3)	0.0111 (3)	0.0003 (2)	0.0029 (3)	0.0011 (3)
C22	0.0114 (3)	0.0083 (3)	0.0098 (3)	−0.0003 (2)	0.0006 (3)	−0.0008 (2)
C31	0.0092 (3)	0.0101 (3)	0.0103 (3)	−0.0007 (2)	−0.0024 (3)	−0.0001 (3)
C32	0.0130 (3)	0.0082 (3)	0.0104 (3)	0.0002 (3)	0.0010 (3)	−0.0014 (2)
C41	0.0159 (4)	0.0157 (4)	0.0106 (3)	0.0059 (3)	0.0016 (3)	0.0012 (3)
C42	0.0139 (3)	0.0111 (3)	0.0096 (3)	0.0003 (3)	0.0015 (3)	0.0033 (3)
O1W	0.0181 (3)	0.0159 (3)	0.0211 (3)	0.0013 (2)	0.0053 (3)	0.0038 (2)
O2W	0.0237 (4)	0.0212 (3)	0.0250 (3)	0.0040 (3)	0.0017 (3)	−0.0079 (3)

Geometric parameters (Å, º)

K1—O11	2.6746 (11)	N1—C22	1.5010 (11)
K1—O1W	2.7350 (11)	N1—C1	1.5038 (11)
K1—O12^i	2.7447 (9)	N1—H1	0.9300
K1—O22^ii	2.7650 (9)	N2—C32	1.4978 (11)
K1—O32	2.8129 (10)	N2—C42	1.5001 (10)
K1—O21	2.9255 (9)	N2—C2	1.5035 (11)
K1—O31^iii	3.1269 (12)	N2—H2	0.9300
K1—K2^ii	3.6987 (10)	C1—C2	1.5163 (11)
K1—K2	4.6515 (11)	C1—H1A	0.9900
K2—O11^ii	2.7138 (9)	C1—H1B	0.9900
K2—O21	2.7836 (9)	C2—H2A	0.9900
K2—O41^iv	2.8218 (12)	C2—H2B	0.9900
K2—O2W	2.8502 (12)	C11—C12	1.5326 (12)
K2—O42^iv	2.8675 (12)	C12—H12A	0.9900
K2—O31^v	2.9309 (9)	C12—H12B	0.9900
K2—O22	2.9641 (12)	C21—C22	1.5316 (12)
O11—C11	1.2560 (10)	C22—H22A	0.9900
O12—C11	1.2505 (10)	C22—H22B	0.9900
O21—C21	1.2652 (10)	C31—C32	1.5252 (12)
O22—C21	1.2498 (10)	C32—H32A	0.9900
O31—C31	1.2580 (10)	C32—H32B	0.9900
O32—C31	1.2579 (10)	C41—C42	1.5256 (13)
O41—C41	1.2588 (11)	C42—H42A	0.9900
O42—C41	1.2457 (12)	C42—H42B	0.9900
N1—C12	1.4959 (10)
O11—K1—O1W	153.56 (2)	C11—O11—K1	147.37 (6)
O11—K1—O12^i	123.57 (3)	C11—O11—K2^ii	125.89 (5)
O1W—K1—O12^i	78.32 (3)	K1—O11—K2^ii	86.69 (3)
O11—K1—O22^ii	98.92 (3)	C11—O12—K1^vi	131.04 (6)
O1W—K1—O22^ii	85.26 (3)	C21—O21—K2	97.18 (5)
O12^i—K1—O22^ii	109.44 (3)	C21—O21—K1	124.23 (5)
O11—K1—O32	77.43 (3)	K2—O21—K1	109.10 (3)
O1W—K1—O32	86.95 (3)	C21—O22—K1^ii	150.23 (6)
O12^i—K1—O32	94.39 (3)	C21—O22—K2	89.08 (5)
O22^ii—K1—O32	152.77 (2)	K1^ii—O22—K2	80.34 (2)
O11—K1—O21	74.75 (3)	C31—O31—K2^vii	131.82 (5)
O1W—K1—O21	79.43 (3)	C31—O31—K1^viii	115.48 (5)
O12^i—K1—O21	150.82 (2)	K2^vii—O31—K1^viii	75.18 (2)
O22^ii—K1—O21	87.18 (3)	C31—O32—K1	154.08 (5)
O32—K1—O21	65.73 (3)	C41—O41—K2^iv	93.64 (6)
O11—K1—O31^iii	68.22 (3)	C41—O42—K2^iv	91.80 (6)
O1W—K1—O31^iii	135.93 (3)	C12—N1—C22	112.17 (6)
O12^i—K1—O31^iii	78.73 (3)	C12—N1—C1	109.65 (6)
O22^ii—K1—O31^iii	67.87 (2)	C22—N1—C1	113.01 (6)
O32—K1—O31^iii	131.93 (2)	C32—N2—C42	110.61 (6)
O21—K1—O31^iii	130.39 (2)	C32—N2—C2	112.83 (6)
O11^ii—K2—O21	126.37 (3)	C42—N2—C2	108.90 (6)
O11^ii—K2—O41^iv	78.36 (3)	N1—C1—C2	114.78 (7)
O21—K2—O41^iv	105.12 (3)	N2—C2—C1	115.54 (7)
O11^ii—K2—O2W	122.23 (3)	O12—C11—O11	127.98 (8)
O21—K2—O2W	93.95 (3)	O12—C11—C12	115.05 (7)
O41^iv—K2—O2W	134.10 (3)	O11—C11—C12	116.95 (7)
O11^ii—K2—O42^iv	92.11 (3)	N1—C12—C11	111.52 (7)
O21—K2—O42^iv	129.51 (2)	O22—C21—O21	126.72 (8)
O41^iv—K2—O42^iv	46.37 (3)	O22—C21—C22	116.05 (7)
O2W—K2—O42^iv	89.45 (3)	O21—C21—C22	117.24 (7)
O11^ii—K2—O31^v	70.80 (3)	N1—C22—C21	112.00 (6)
O21—K2—O31^v	109.20 (3)	O32—C31—O31	126.95 (8)
O41^iv—K2—O31^v	143.16 (2)	O32—C31—C32	118.93 (7)
O2W—K2—O31^v	56.45 (2)	O31—C31—C32	114.11 (7)
O42^iv—K2—O31^v	114.25 (3)	N2—C32—C31	113.24 (7)
O11^ii—K2—O22	93.35 (3)	O42—C41—O41	126.90 (9)
O21—K2—O22	45.913 (19)	O42—C41—C42	118.05 (8)
O41^iv—K2—O22	134.67 (3)	O41—C41—C42	115.03 (8)
O2W—K2—O22	88.02 (3)	N2—C42—C41	111.53 (7)
O42^iv—K2—O22	174.52 (2)	H11W—O1W—H12W	105.1
O31^v—K2—O22	68.15 (3)	H22W—O2W—H21W	104.3
C12—N1—C1—C2	−177.17 (6)	O22—C21—C22—N1	177.84 (7)
C22—N1—C1—C2	56.90 (9)	O21—C21—C22—N1	−2.74 (10)
C32—N2—C2—C1	57.78 (9)	C42—N2—C32—C31	147.71 (7)
C42—N2—C2—C1	−178.99 (6)	C2—N2—C32—C31	−90.02 (8)
N1—C1—C2—N2	66.78 (9)	O32—C31—C32—N2	−6.78 (10)
C22—N1—C12—C11	−69.17 (8)	O31—C31—C32—N2	174.33 (7)
C1—N1—C12—C11	164.42 (6)	C32—N2—C42—C41	−71.56 (8)
O12—C11—C12—N1	170.42 (7)	C2—N2—C42—C41	163.89 (6)
O11—C11—C12—N1	−11.14 (10)	O42—C41—C42—N2	−16.05 (11)
C12—N1—C22—C21	138.63 (7)	O41—C41—C42—N2	165.31 (7)
C1—N1—C22—C21	−96.80 (8)

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+2; (v) −x+1/2, y−1/2, −z+3/2; (vi) x−1/2, −y+3/2, z−1/2; (vii) −x+1/2, y+1/2, −z+3/2; (viii) x−1/2, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O32	0.93	2.01	2.8029 (12)	142
N1—H1···O21	0.93	2.19	2.6869 (11)	112
N2—H2···O21	0.93	2.04	2.8617 (12)	147
N2—H2···O32	0.93	2.32	2.7425 (11)	107
N2—H2···O42	0.93	2.38	2.7004 (13)	100
O1W—H12W···O42	0.86	1.90	2.7384 (13)	166
O1W—H11W···O41^iv	0.86	1.88	2.7226 (12)	167
O2W—H21W···O1W^iv	0.86	2.06	2.8588 (14)	154
O2W—H22W···O31^v	0.86	1.90	2.7350 (11)	164
C1—H1A···O31^vi	0.99	2.35	3.2480 (15)	150
C2—H2A···O1W^ix	0.99	2.60	3.5644 (16)	165
C1—H1B···O12^viii	0.99	2.50	3.0316 (12)	114
C22—H22A···O41^x	0.99	2.28	3.2205 (14)	159
C32—H32A···O12^xi	0.99	2.33	3.2703 (14)	158
C32—H32B···O11^viii	0.99	2.48	3.3647 (12)	148
C42—H42A···O2W	0.99	2.39	3.2365 (14)	143
C42—H42B···O2W^xii	0.99	2.36	3.3349 (15)	166

Symmetry codes: (iv) −x+1, −y+1, −z+2; (v) −x+1/2, y−1/2, −z+3/2; (vi) x−1/2, −y+3/2, z−1/2; (viii) x−1/2, −y+3/2, z+1/2; (ix) x−1, y, z; (x) x, y, z−1; (xi) x, y, z+1; (xii) −x, −y+1, −z+2.

(II) tripotassium 2-({2-[bis(carboxylatomethyl)amino]ethyl}(carboxylatomethyl)azaniumyl)acetate dihydrate

Crystal data

3K^+·C10H13N2O8^3^−·2H2O	Z = 2
Mr = 442.56	F(000) = 456
Triclinic, P1	Dx = 1.749 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.074 (3) Å	Cell parameters from 15331 reflections
b = 9.987 (3) Å	θ = 4.6–38.5°
c = 11.045 (3) Å	µ = 0.87 mm^−1
α = 101.68 (3)°	T = 110 K
β = 102.19 (3)°	Block, colourless
γ = 96.85 (3)°	0.27 × 0.19 × 0.19 mm
V = 840.2 (5) Å^3

Data collection

Oxford Diffraction Xcalibur PX KM-4-CCD diffractometer	9029 independent reflections
Radiation source: fine-focus sealed tube	7083 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ϕ and ω scans	θmax = 38.5°, θmin = 4.6°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	h = −12→14
Tmin = 0.808, Tmax = 0.886	k = −17→17
24301 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.036P)^2] where P = (Fo^2 + 2Fc^2)/3
9029 reflections	(Δ/σ)max = 0.002
226 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
K1	0.29419 (2)	0.897638 (16)	0.399042 (15)	0.01204 (3)
K2	0.44262 (2)	0.858824 (16)	0.776214 (15)	0.01304 (3)
K3	0.04772 (2)	1.175392 (17)	0.197522 (16)	0.01501 (4)
O11	0.19850 (8)	0.62235 (6)	0.37444 (5)	0.01568 (11)
O12	−0.00447 (8)	0.45612 (6)	0.23735 (6)	0.01919 (12)
O21	0.24837 (8)	0.93201 (6)	0.16198 (5)	0.01876 (12)
O22	0.27947 (7)	0.91022 (6)	−0.03641 (5)	0.01477 (10)
O31	0.63291 (7)	0.68285 (6)	0.67029 (5)	0.01262 (10)
O32	0.56755 (7)	0.83383 (5)	0.55001 (5)	0.01175 (9)
O41	0.98013 (7)	0.97410 (6)	0.32934 (6)	0.01934 (12)
O42	0.69826 (7)	0.95450 (6)	0.32534 (6)	0.01763 (11)
N1	0.34185 (8)	0.66795 (6)	0.16978 (6)	0.01018 (10)
N2	0.67292 (8)	0.69855 (6)	0.35625 (6)	0.00924 (10)
H2	0.5962	0.7610	0.3542	0.011*
C1	0.44530 (9)	0.55601 (7)	0.17190 (7)	0.01126 (12)
H1A	0.4254	0.4986	0.0842	0.014*
H1B	0.4062	0.4957	0.2249	0.014*
C2	0.63588 (9)	0.60959 (8)	0.22374 (7)	0.01151 (12)
H2A	0.6984	0.5302	0.2243	0.014*
H2B	0.6775	0.6643	0.1675	0.014*
C11	0.11830 (9)	0.55599 (8)	0.26489 (7)	0.01243 (12)
C12	0.16162 (9)	0.60412 (8)	0.15001 (7)	0.01358 (13)
H12A	0.1336	0.5232	0.0762	0.016*
H12B	0.0872	0.6719	0.1280	0.016*
C21	0.28766 (9)	0.86909 (8)	0.06529 (7)	0.01100 (12)
C22	0.35924 (10)	0.73331 (8)	0.06427 (7)	0.01230 (12)
H22A	0.3004	0.6660	−0.0168	0.015*
H22B	0.4828	0.7519	0.0652	0.015*
C31	0.61234 (9)	0.72172 (7)	0.56826 (6)	0.00932 (11)
C32	0.64230 (10)	0.62151 (7)	0.45385 (7)	0.01175 (12)
H32A	0.7430	0.5777	0.4814	0.014*
H32B	0.5406	0.5474	0.4169	0.014*
C41	0.84165 (10)	0.91617 (8)	0.34322 (7)	0.01214 (12)
C42	0.84879 (9)	0.78345 (7)	0.39235 (7)	0.01150 (12)
H42A	0.9284	0.7294	0.3550	0.014*
H42B	0.8921	0.8077	0.4862	0.014*
O2W	0.15351 (9)	0.68563 (6)	0.62234 (6)	0.02288 (13)
H21W	0.1025	0.6215	0.6490	0.034*
H22W	0.1484	0.6523	0.5435	0.034*
O3W	0.15902 (9)	1.16026 (7)	−0.02942 (6)	0.02384 (13)
H31W	0.2025	1.0854	−0.0317	0.036*
H32W	0.0774	1.1427	−0.0973	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.01345 (7)	0.00980 (6)	0.01197 (6)	0.00261 (5)	0.00048 (5)	0.00286 (5)
K2	0.01559 (7)	0.01287 (7)	0.01388 (7)	0.00500 (5)	0.00732 (5)	0.00498 (5)
K3	0.01370 (7)	0.01448 (7)	0.01500 (7)	−0.00094 (5)	0.00033 (5)	0.00450 (5)
O11	0.0208 (3)	0.0138 (2)	0.0135 (2)	0.0025 (2)	0.0070 (2)	0.00308 (19)
O12	0.0152 (3)	0.0175 (3)	0.0248 (3)	−0.0023 (2)	0.0067 (2)	0.0058 (2)
O21	0.0285 (3)	0.0206 (3)	0.0109 (2)	0.0130 (2)	0.0072 (2)	0.0044 (2)
O22	0.0179 (3)	0.0175 (3)	0.0127 (2)	0.0062 (2)	0.0062 (2)	0.0076 (2)
O31	0.0156 (2)	0.0135 (2)	0.0100 (2)	0.00381 (19)	0.00318 (18)	0.00456 (18)
O32	0.0143 (2)	0.0096 (2)	0.0126 (2)	0.00357 (18)	0.00414 (18)	0.00347 (18)
O41	0.0140 (3)	0.0227 (3)	0.0254 (3)	0.0016 (2)	0.0068 (2)	0.0133 (2)
O42	0.0148 (3)	0.0155 (3)	0.0269 (3)	0.0064 (2)	0.0065 (2)	0.0106 (2)
N1	0.0094 (2)	0.0118 (2)	0.0102 (2)	0.00195 (19)	0.00275 (19)	0.0041 (2)
N2	0.0098 (2)	0.0090 (2)	0.0097 (2)	0.00305 (19)	0.00310 (19)	0.00259 (19)
C1	0.0124 (3)	0.0105 (3)	0.0106 (3)	0.0024 (2)	0.0024 (2)	0.0022 (2)
C2	0.0119 (3)	0.0135 (3)	0.0096 (3)	0.0041 (2)	0.0035 (2)	0.0017 (2)
C11	0.0107 (3)	0.0114 (3)	0.0172 (3)	0.0040 (2)	0.0060 (2)	0.0039 (2)
C12	0.0100 (3)	0.0172 (3)	0.0127 (3)	0.0001 (2)	0.0014 (2)	0.0044 (3)
C21	0.0099 (3)	0.0130 (3)	0.0101 (3)	0.0018 (2)	0.0017 (2)	0.0033 (2)
C22	0.0145 (3)	0.0143 (3)	0.0103 (3)	0.0042 (2)	0.0047 (2)	0.0051 (2)
C31	0.0078 (3)	0.0094 (3)	0.0102 (3)	0.0005 (2)	0.0020 (2)	0.0018 (2)
C32	0.0170 (3)	0.0088 (3)	0.0107 (3)	0.0029 (2)	0.0046 (2)	0.0033 (2)
C41	0.0134 (3)	0.0122 (3)	0.0116 (3)	0.0025 (2)	0.0031 (2)	0.0043 (2)
C42	0.0093 (3)	0.0117 (3)	0.0140 (3)	0.0021 (2)	0.0021 (2)	0.0044 (2)
O2W	0.0332 (4)	0.0168 (3)	0.0177 (3)	−0.0035 (2)	0.0100 (3)	0.0022 (2)
O3W	0.0313 (4)	0.0185 (3)	0.0212 (3)	0.0066 (3)	0.0059 (3)	0.0026 (2)

Geometric parameters (Å, º)

K1—O21	2.6637 (9)	O41—C41	1.2499 (10)
K1—O32^i	2.6767 (11)	O42—C41	1.2512 (10)
K1—O32	2.6962 (11)	N1—C22	1.4694 (10)
K1—O11	2.7077 (11)	N1—C12	1.4696 (11)
K1—O41^ii	2.7351 (12)	N1—C1	1.4741 (11)
K1—O42^i	3.0873 (12)	N2—C32	1.4894 (10)
K1—N1	3.1769 (13)	N2—C42	1.4937 (11)
K1—K1^i	3.6881 (18)	N2—C2	1.4987 (11)
K1—K2^i	4.0729 (13)	N2—H2	0.9300
K2—O42^i	2.6156 (10)	C1—C2	1.5131 (12)
K2—O22^iii	2.6767 (10)	C1—H1A	0.9900
K2—O31	2.7182 (11)	C1—H1B	0.9900
K2—O2W	2.7386 (15)	C2—H2A	0.9900
K2—O32	2.8625 (10)	C2—H2B	0.9900
K2—O21^i	2.9180 (14)	C11—C12	1.5354 (11)
K2—K3^iv	4.0096 (15)	C12—H12A	0.9900
K2—K3^i	4.1238 (16)	C12—H12B	0.9900
K3—O31^i	2.7363 (14)	C21—C22	1.5350 (11)
K3—O41^ii	2.7781 (10)	C22—H22A	0.9900
K3—O22^v	2.7814 (14)	C22—H22B	0.9900
K3—O3W	2.8185 (10)	C31—C32	1.5270 (11)
K3—O12^vi	2.8447 (11)	C32—H32A	0.9900
K3—O2W^iv	3.0512 (12)	C32—H32B	0.9900
K3—O21	3.0836 (12)	C41—C42	1.5333 (11)
O11—C11	1.2508 (11)	C42—H42A	0.9900
O12—C11	1.2585 (11)	C42—H42B	0.9900
O21—C21	1.2471 (10)	O2W—H21W	0.8547
O22—C21	1.2636 (9)	O2W—H22W	0.8577
O31—C31	1.2496 (9)	O3W—H31W	0.8609
O32—C31	1.2579 (9)	O3W—H32W	0.8589
O21—K1—O32^i	80.71 (4)	O22^v—K3—O2W^iv	82.01 (4)
O21—K1—O32	130.07 (3)	O3W—K3—O2W^iv	148.18 (2)
O32^i—K1—O32	93.30 (4)	O12^vi—K3—O2W^iv	53.69 (3)
O21—K1—O11	105.46 (4)	O31^i—K3—O21	81.94 (4)
O32^i—K1—O11	171.021 (19)	O41^ii—K3—O21	64.60 (3)
O32—K1—O11	77.74 (4)	O22^v—K3—O21	108.05 (4)
O21—K1—O41^ii	71.18 (3)	O3W—K3—O21	71.32 (3)
O32^i—K1—O41^ii	87.59 (4)	O12^vi—K3—O21	157.09 (2)
O32—K1—O41^ii	158.60 (2)	O2W^iv—K3—O21	140.42 (2)
O11—K1—O41^ii	100.50 (4)	K1—O21—K2^i	93.61 (4)
O21—K1—O42^i	143.15 (2)	K1—O21—K3	96.82 (3)
O32^i—K1—O42^i	68.87 (3)	K2^i—O21—K3	86.76 (3)
O32—K1—O42^i	73.68 (3)	K2^vii—O22—K3^v	94.53 (3)
O11—K1—O42^i	107.42 (3)	K2—O31—K3^i	98.23 (4)
O41^ii—K1—O42^i	86.81 (4)	K1^i—O32—K1	86.70 (4)
O21—K1—N1	57.41 (3)	K1^i—O32—K2	94.60 (3)
O32^i—K1—N1	124.19 (3)	K1—O32—K2	97.95 (3)
O32—K1—N1	88.57 (4)	K1^viii—O41—K3^viii	102.76 (3)
O11—K1—N1	56.99 (3)	K2^i—O42—K1^i	94.35 (3)
O41^ii—K1—N1	108.56 (4)	C22—N1—C12	109.34 (6)
O42^i—K1—N1	159.182 (19)	C22—N1—C1	110.20 (6)
O42^i—K2—O22^iii	89.86 (3)	C12—N1—C1	107.16 (6)
O42^i—K2—O31	125.88 (3)	C22—N1—K1	108.47 (5)
O22^iii—K2—O31	143.60 (2)	C12—N1—K1	88.75 (5)
O42^i—K2—O2W	82.71 (4)	C1—N1—K1	129.66 (5)
O22^iii—K2—O2W	90.08 (4)	C32—N2—C42	112.28 (6)
O31—K2—O2W	88.23 (4)	C32—N2—C2	114.23 (6)
O42^i—K2—O32	78.78 (3)	C42—N2—C2	110.77 (6)
O22^iii—K2—O32	168.208 (18)	N1—C1—C2	112.98 (7)
O31—K2—O32	47.26 (2)	N2—C2—C1	111.15 (7)
O2W—K2—O32	85.38 (4)	O11—C11—O12	126.46 (8)
O42^i—K2—O21^i	82.54 (3)	O11—C11—C12	118.57 (7)
O22^iii—K2—O21^i	108.46 (4)	O12—C11—C12	114.83 (7)
O31—K2—O21^i	85.40 (3)	N1—C12—C11	114.75 (6)
O2W—K2—O21^i	156.19 (2)	O21—C21—O22	125.11 (7)
O32—K2—O21^i	73.48 (4)	O21—C21—C22	120.74 (7)
O31^i—K3—O41^ii	104.20 (3)	O22—C21—C22	114.11 (7)
O31^i—K3—O22^v	165.409 (19)	N1—C22—C21	116.01 (6)
O41^ii—K3—O22^v	89.89 (3)	O31—C31—O32	126.68 (7)
O31^i—K3—O3W	88.59 (4)	O31—C31—C32	116.41 (6)
O41^ii—K3—O3W	131.33 (3)	O32—C31—C32	116.91 (6)
O22^v—K3—O3W	84.80 (4)	N2—C32—C31	109.49 (6)
O31^i—K3—O12^vi	77.61 (4)	O41—C41—O42	128.32 (7)
O41^ii—K3—O12^vi	130.68 (3)	O41—C41—C42	116.12 (7)
O22^v—K3—O12^vi	90.39 (4)	O42—C41—C42	115.53 (7)
O3W—K3—O12^vi	97.77 (3)	N2—C42—C41	109.40 (6)
O31^i—K3—O2W^iv	97.12 (4)	K2—O2W—K3^iv	87.49 (4)
O41^ii—K3—O2W^iv	77.58 (3)	H31W—O3W—H32W	105.3
N1—C1—C2—N2	58.12 (8)	C42—N2—C32—C31	75.56 (8)
C22—N1—C12—C11	−169.06 (6)	C2—N2—C32—C31	−157.23 (6)
C1—N1—C12—C11	71.51 (8)	O31—C31—C32—N2	−160.49 (6)
O11—C11—C12—N1	31.84 (10)	O32—C31—C32—N2	20.36 (9)
O12—C11—C12—N1	−152.21 (7)	C32—N2—C42—C41	−146.30 (6)
C12—N1—C22—C21	73.87 (9)	C2—N2—C42—C41	84.66 (7)
C1—N1—C22—C21	−168.59 (6)	O41—C41—C42—N2	−157.85 (7)
O21—C21—C22—N1	13.17 (10)	O42—C41—C42—N2	23.95 (9)
O22—C21—C22—N1	−169.15 (6)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z; (iii) x, y, z+1; (iv) −x, −y+2, −z+1; (v) −x, −y+2, −z; (vi) x, y+1, z; (vii) x, y, z−1; (viii) x+1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O42	0.93	2.12	2.6364 (11)	114
N2—H2···N1	0.93	2.50	2.9505 (15)	110
O2W—H21W···O12^ix	0.85	1.86	2.6690 (12)	157
O2W—H22W···O11	0.86	1.96	2.7933 (12)	162
O3W—H31W···O22	0.86	1.92	2.7786 (12)	175
O3W—H32W···O41^x	0.86	2.51	3.2101 (16)	139
O3W—H32W···O21^v	0.86	2.55	3.2417 (17)	138
C1—H1B···O31^xi	0.99	2.34	3.3040 (13)	164
C2—H2A···O12^viii	0.99	2.58	3.4313 (15)	144
C32—H32B···O31^xi	0.99	2.44	3.3870 (18)	161
C42—H42A···O11^viii	0.99	2.53	3.4338 (15)	152

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

(III) tetrapotassium 2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetate 3.92-hydrate

Crystal data

4K^+·C10H12N2O8^4^−·3.92H2O	Z = 16
Mr = 515.21	F(000) = 4242.2
Monoclinic, C2/c	Dx = 1.636 Mg m^−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 30.033 (9) Å	Cell parameters from 29729 reflections
b = 9.700 (3) Å	µ = 0.91 mm^−1
c = 31.513 (9) Å	T = 90 K
β = 114.27 (3)°	Block, colourless
V = 8369 (5) Å^3	0.21 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur PX KM-4-CCD diffractometer	18115 independent reflections
Radiation source: fine-focus sealed tube	13121 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ϕ and ω scans	θmax = 35.1°, θmin = 2.6°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	h = −47→48
Tmin = 0.831, Tmax = 0.931	k = −12→15
64671 measured reflections	l = −50→46

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0205P)^2] where P = (Fo^2 + 2Fc^2)/3
18115 reflections	(Δ/σ)max = 0.004
549 parameters	Δρmax = 0.50 e Å^−3
3 restraints	Δρmin = −0.33 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
K1	0.325416 (7)	0.32720 (2)	0.513644 (7)	0.01090 (4)
K2	0.336461 (7)	0.31143 (2)	0.811023 (7)	0.01318 (4)
K3	0.432897 (7)	0.47625 (2)	0.952110 (7)	0.01352 (4)
K4	0.207494 (7)	0.65498 (2)	0.518244 (8)	0.01452 (4)
K5	0.245709 (7)	0.19666 (2)	0.691611 (8)	0.01520 (4)
K6	0.283592 (8)	−0.17065 (2)	0.642237 (7)	0.01367 (4)
K8	0.369299 (7)	0.09504 (2)	0.430265 (7)	0.01313 (4)
K7	0.50603 (3)	0.82119 (9)	0.56904 (5)	0.01472 (18)	0.947 (8)
K71	0.5125 (6)	0.8038 (17)	0.5793 (8)	0.028 (3)*	0.053 (8)
O11A	0.27134 (2)	0.24397 (7)	0.56576 (2)	0.01476 (14)
O12A	0.26410 (2)	0.10075 (7)	0.61857 (2)	0.01443 (14)
O21A	0.35747 (2)	0.05963 (7)	0.51404 (2)	0.01306 (13)
O22A	0.41743 (3)	−0.09025 (7)	0.55134 (3)	0.01853 (15)
O31A	0.30195 (2)	0.75921 (7)	0.57208 (3)	0.01524 (14)
O32A	0.30518 (3)	0.59163 (7)	0.52508 (2)	0.01516 (14)
O41A	0.48191 (2)	0.55071 (7)	0.54930 (3)	0.01534 (14)
O42A	0.42462 (3)	0.38654 (7)	0.53134 (3)	0.01611 (14)
N1A	0.37208 (3)	0.18150 (8)	0.60024 (3)	0.01031 (14)
N2A	0.39066 (3)	0.48783 (8)	0.59501 (3)	0.01042 (15)
C1A	0.39195 (3)	0.27498 (10)	0.64046 (3)	0.01209 (18)
H1A1	0.4138	0.2218	0.6679	0.015*
H1A2	0.3646	0.3104	0.6472	0.015*
C2A	0.42017 (3)	0.39689 (10)	0.63351 (3)	0.01197 (17)
H2A1	0.4337	0.4515	0.6626	0.014*
H2A2	0.4480	0.3616	0.6276	0.014*
C11A	0.28732 (3)	0.15150 (10)	0.59625 (3)	0.01108 (17)
C12A	0.33734 (3)	0.08717 (9)	0.60690 (3)	0.01149 (17)
H12A	0.3515	0.0545	0.6395	0.014*
H12B	0.3328	0.0058	0.5866	0.014*
C21A	0.39313 (3)	0.01840 (10)	0.54937 (3)	0.01160 (17)
C22A	0.41104 (3)	0.10296 (10)	0.59446 (3)	0.01346 (18)
H22A	0.4261	0.0398	0.6213	0.016*
H22B	0.4366	0.1678	0.5947	0.016*
C31A	0.31911 (3)	0.64746 (10)	0.56436 (3)	0.01180 (17)
C32A	0.35803 (3)	0.57615 (10)	0.60696 (3)	0.01298 (18)
H32A	0.3777	0.6473	0.6294	0.016*
H32B	0.3416	0.5197	0.6225	0.016*
C41A	0.44518 (3)	0.49473 (10)	0.55224 (3)	0.01170 (17)
C42A	0.42297 (3)	0.57182 (10)	0.58119 (3)	0.01244 (18)
H42A	0.4498	0.6080	0.6096	0.015*
H42B	0.4043	0.6518	0.5630	0.015*
O11B	0.31725 (3)	0.37620 (7)	0.71316 (3)	0.01880 (15)
O12B	0.28479 (3)	0.58161 (7)	0.68393 (2)	0.01703 (15)
O21B	0.34486 (3)	0.58281 (7)	0.83792 (3)	0.01810 (15)
O22B	0.40704 (3)	0.71089 (8)	0.88539 (3)	0.02460 (18)
O31B	0.35994 (13)	−0.08711 (13)	0.71908 (5)	0.0237 (6)	0.793 (11)
O32B	0.32612 (7)	0.0400 (3)	0.75727 (7)	0.0177 (4)	0.793 (11)
C31B	0.36049 (11)	0.0121 (2)	0.74467 (6)	0.0135 (4)	0.793 (11)
O31C	0.3447 (3)	−0.0805 (6)	0.7226 (2)	0.0212 (14)*	0.207 (11)
O32C	0.3213 (2)	0.0700 (8)	0.7639 (3)	0.0146 (13)*	0.207 (11)
C31C	0.3498 (3)	0.0241 (8)	0.7484 (3)	0.0090 (15)*	0.207 (11)
O41B	0.45066 (3)	0.07456 (7)	0.92229 (2)	0.01589 (14)
O42B	0.42302 (3)	0.27803 (7)	0.88782 (2)	0.01538 (14)
N1B	0.39593 (3)	0.49706 (8)	0.78624 (3)	0.01083 (15)
N2B	0.41635 (3)	0.18598 (8)	0.80185 (3)	0.01113 (15)
C1B	0.43060 (3)	0.41780 (10)	0.77379 (3)	0.01328 (18)
H1B1	0.4574	0.4796	0.7752	0.016*
H1B2	0.4136	0.3849	0.7413	0.016*
C2B	0.45250 (3)	0.29387 (10)	0.80558 (4)	0.01342 (18)
H2B1	0.4784	0.2530	0.7978	0.016*
H2B2	0.4680	0.3263	0.8382	0.016*
C11B	0.31870 (3)	0.50403 (10)	0.71240 (3)	0.01312 (18)
C12B	0.36341 (3)	0.58134 (10)	0.74702 (3)	0.01345 (18)
H12C	0.3824	0.6177	0.7301	0.016*
H12D	0.3520	0.6611	0.7595	0.016*
C21B	0.38757 (4)	0.63040 (10)	0.85129 (3)	0.01412 (19)
C22B	0.42053 (3)	0.58340 (10)	0.82740 (3)	0.01270 (18)
H22C	0.4338	0.6660	0.8182	0.015*
H22D	0.4485	0.5314	0.8502	0.015*
C32B	0.40331 (4)	0.10777 (11)	0.75865 (4)	0.0173 (2)
H32C	0.4317	0.0504	0.7615	0.021*
H32D	0.3973	0.1739	0.7329	0.021*
C41B	0.43636 (3)	0.15612 (10)	0.88734 (3)	0.01240 (18)
C42B	0.43528 (3)	0.09380 (10)	0.84225 (3)	0.01318 (18)
H42C	0.4689	0.0659	0.8476	0.016*
H42D	0.4149	0.0095	0.8349	0.016*
O1W	0.33361 (3)	0.37898 (7)	0.42378 (3)	0.01882 (15)
H11W	0.3029	0.3765	0.4120	0.028*
H12W	0.3414	0.3770	0.4010	0.028*
O2W	0.26245 (3)	−0.19725 (8)	0.72921 (3)	0.01893 (15)
H21W	0.2712	−0.2651	0.7178	0.028*
H22W	0.2839	−0.1354	0.7360	0.028*
O3W	0.39938 (3)	0.20579 (8)	0.96874 (3)	0.02086 (16)
H31W	0.4172	0.1716	0.9568	0.031*
H32W	0.4036	0.1608	0.9929	0.031*
O4W	0.23142 (2)	0.47149 (7)	0.59016 (2)	0.01698 (15)
H41W	0.2425	0.3993	0.5835	0.025*
H42W	0.2493	0.4941	0.6176	0.025*
O5W	0.46427 (3)	0.17971 (8)	0.50076 (3)	0.01940 (15)
H51W	0.4535	0.2472	0.5105	0.029*
H52W	0.4882	0.1483	0.5237	0.029*
O6W	0.18583 (3)	−0.17786 (8)	0.59388 (3)	0.0307 (2)
H61W	0.1803	−0.0947	0.5862	0.046*
H62W	0.1603	−0.2211	0.5774	0.046*
O7W	0.31110 (7)	0.0333 (4)	0.33717 (4)	0.0284 (6)	0.892 (10)
H71W	0.2891	−0.0233	0.3334	0.043*	0.892
H72W	0.3188	0.0078	0.3157	0.043*	0.892
O71W	0.3206 (4)	−0.0231 (16)	0.3416 (3)	0.012 (2)*	0.108 (10)
O8W	0.48227 (10)	0.8297 (3)	0.65078 (11)	0.0241 (9)	0.267 (2)
H81W	0.4566	0.8444	0.6268	0.036*	0.267 (2)
H82W	0.4692	0.8344	0.6700	0.036*	0.267 (2)
O9W	0.4517 (2)	0.7920 (9)	0.7236 (4)	0.0444 (19)	0.282 (14)
H91W	0.4241	0.8223	0.7199	0.067*	0.282 (14)
H92W	0.4737	0.8150	0.7494	0.067*	0.282 (14)
O91W	0.44705 (18)	0.8398 (13)	0.7038 (5)	0.053 (3)	0.298 (14)
H93W	0.4598	0.7957	0.7289	0.080*	0.298 (14)
H94W	0.4174	0.8551	0.6971	0.080*	0.298 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.01167 (8)	0.01053 (9)	0.01021 (9)	0.00043 (7)	0.00421 (7)	0.00002 (7)
K2	0.01040 (8)	0.01374 (9)	0.01420 (10)	−0.00041 (7)	0.00383 (7)	0.00052 (8)
K3	0.01345 (9)	0.01559 (10)	0.01247 (10)	−0.00198 (8)	0.00630 (8)	−0.00206 (8)
K4	0.01353 (9)	0.01424 (10)	0.01457 (10)	−0.00235 (8)	0.00454 (8)	0.00157 (8)
K5	0.01299 (9)	0.01951 (11)	0.01329 (10)	−0.00413 (8)	0.00558 (8)	−0.00445 (8)
K6	0.01728 (9)	0.01218 (9)	0.01244 (10)	−0.00076 (8)	0.00701 (8)	0.00000 (8)
K8	0.01249 (9)	0.01444 (10)	0.01240 (10)	−0.00017 (7)	0.00504 (8)	0.00062 (8)
K7	0.01196 (19)	0.01283 (19)	0.0206 (3)	−0.00144 (12)	0.0079 (2)	−0.00307 (18)
O11A	0.0140 (3)	0.0158 (3)	0.0152 (4)	0.0025 (3)	0.0067 (3)	0.0046 (3)
O12A	0.0142 (3)	0.0157 (3)	0.0166 (4)	−0.0002 (3)	0.0096 (3)	0.0016 (3)
O21A	0.0133 (3)	0.0134 (3)	0.0118 (3)	0.0000 (3)	0.0045 (3)	−0.0012 (3)
O22A	0.0198 (4)	0.0144 (3)	0.0220 (4)	0.0059 (3)	0.0092 (3)	0.0004 (3)
O31A	0.0172 (3)	0.0116 (3)	0.0187 (4)	0.0019 (3)	0.0091 (3)	−0.0016 (3)
O32A	0.0167 (3)	0.0133 (3)	0.0132 (3)	0.0026 (3)	0.0038 (3)	−0.0010 (3)
O41A	0.0120 (3)	0.0183 (3)	0.0184 (4)	−0.0016 (3)	0.0090 (3)	0.0006 (3)
O42A	0.0166 (3)	0.0161 (3)	0.0180 (4)	−0.0029 (3)	0.0095 (3)	−0.0042 (3)
N1A	0.0092 (3)	0.0117 (4)	0.0113 (4)	−0.0009 (3)	0.0055 (3)	−0.0013 (3)
N2A	0.0096 (3)	0.0120 (4)	0.0109 (4)	0.0010 (3)	0.0054 (3)	0.0017 (3)
C1A	0.0129 (4)	0.0146 (4)	0.0088 (4)	0.0000 (3)	0.0045 (3)	0.0006 (3)
C2A	0.0101 (4)	0.0145 (4)	0.0099 (4)	−0.0010 (3)	0.0027 (3)	−0.0003 (4)
C11A	0.0113 (4)	0.0107 (4)	0.0114 (4)	−0.0014 (3)	0.0049 (3)	−0.0031 (3)
C12A	0.0117 (4)	0.0105 (4)	0.0135 (5)	0.0011 (3)	0.0064 (4)	0.0020 (3)
C21A	0.0108 (4)	0.0113 (4)	0.0154 (5)	−0.0011 (3)	0.0081 (4)	0.0012 (4)
C22A	0.0095 (4)	0.0189 (5)	0.0118 (4)	0.0030 (4)	0.0042 (3)	0.0003 (4)
C31A	0.0104 (4)	0.0117 (4)	0.0149 (5)	−0.0016 (3)	0.0068 (4)	0.0001 (4)
C32A	0.0124 (4)	0.0154 (5)	0.0121 (5)	0.0011 (3)	0.0060 (4)	−0.0016 (4)
C41A	0.0104 (4)	0.0144 (4)	0.0099 (4)	0.0017 (3)	0.0039 (3)	0.0025 (4)
C42A	0.0124 (4)	0.0120 (4)	0.0144 (5)	−0.0018 (3)	0.0070 (4)	−0.0006 (4)
O11B	0.0178 (3)	0.0138 (3)	0.0193 (4)	−0.0033 (3)	0.0021 (3)	−0.0006 (3)
O12B	0.0157 (3)	0.0170 (4)	0.0132 (4)	−0.0014 (3)	0.0007 (3)	0.0017 (3)
O21B	0.0164 (3)	0.0167 (4)	0.0249 (4)	−0.0004 (3)	0.0122 (3)	−0.0020 (3)
O22B	0.0200 (4)	0.0307 (4)	0.0172 (4)	0.0070 (3)	0.0017 (3)	−0.0113 (3)
O31B	0.0328 (11)	0.0153 (5)	0.0195 (6)	−0.0069 (5)	0.0072 (6)	−0.0069 (4)
O32B	0.0168 (6)	0.0187 (8)	0.0161 (6)	−0.0041 (5)	0.0053 (5)	0.0011 (6)
C31B	0.0167 (9)	0.0138 (7)	0.0083 (7)	−0.0019 (6)	0.0035 (6)	0.0023 (5)
O41B	0.0189 (3)	0.0143 (3)	0.0117 (3)	0.0023 (3)	0.0035 (3)	0.0020 (3)
O42B	0.0200 (3)	0.0123 (3)	0.0128 (3)	0.0029 (3)	0.0058 (3)	−0.0008 (3)
N1B	0.0102 (3)	0.0123 (4)	0.0087 (4)	0.0002 (3)	0.0026 (3)	−0.0008 (3)
N2B	0.0122 (3)	0.0111 (4)	0.0097 (4)	−0.0020 (3)	0.0042 (3)	−0.0016 (3)
C1B	0.0137 (4)	0.0137 (4)	0.0141 (5)	−0.0022 (3)	0.0074 (4)	−0.0017 (4)
C2B	0.0102 (4)	0.0139 (4)	0.0167 (5)	−0.0010 (3)	0.0060 (4)	−0.0021 (4)
C11B	0.0129 (4)	0.0163 (5)	0.0100 (4)	−0.0023 (4)	0.0046 (4)	0.0001 (4)
C12B	0.0144 (4)	0.0121 (4)	0.0110 (4)	−0.0022 (3)	0.0023 (4)	0.0010 (4)
C21B	0.0149 (4)	0.0143 (4)	0.0116 (5)	0.0055 (4)	0.0039 (4)	0.0023 (4)
C22B	0.0097 (4)	0.0151 (4)	0.0112 (4)	−0.0006 (3)	0.0021 (3)	−0.0021 (4)
C32B	0.0239 (5)	0.0168 (5)	0.0132 (5)	−0.0040 (4)	0.0095 (4)	−0.0046 (4)
C41B	0.0102 (4)	0.0131 (4)	0.0116 (4)	−0.0004 (3)	0.0022 (3)	−0.0013 (4)
C42B	0.0144 (4)	0.0116 (4)	0.0126 (5)	0.0011 (3)	0.0046 (4)	−0.0008 (4)
O1W	0.0135 (3)	0.0247 (4)	0.0178 (4)	0.0005 (3)	0.0060 (3)	0.0007 (3)
O2W	0.0143 (3)	0.0243 (4)	0.0184 (4)	−0.0016 (3)	0.0070 (3)	−0.0008 (3)
O3W	0.0241 (4)	0.0219 (4)	0.0202 (4)	0.0044 (3)	0.0127 (3)	0.0056 (3)
O4W	0.0165 (3)	0.0186 (4)	0.0135 (4)	0.0035 (3)	0.0038 (3)	−0.0010 (3)
O5W	0.0185 (3)	0.0229 (4)	0.0149 (4)	0.0045 (3)	0.0049 (3)	−0.0033 (3)
O6W	0.0175 (4)	0.0175 (4)	0.0493 (6)	−0.0017 (3)	0.0057 (4)	0.0015 (4)
O7W	0.0246 (6)	0.0450 (15)	0.0164 (5)	−0.0150 (8)	0.0092 (4)	−0.0047 (6)
O8W	0.0213 (15)	0.0220 (16)	0.0272 (18)	0.0008 (12)	0.0080 (13)	−0.0015 (13)
O9W	0.050 (3)	0.047 (3)	0.037 (4)	−0.012 (2)	0.019 (3)	−0.001 (3)
O91W	0.035 (2)	0.069 (5)	0.057 (5)	0.007 (2)	0.020 (2)	−0.011 (4)

Geometric parameters (Å, º)

K1—O32A	2.6942 (10)	O32A—K4^vii	2.7610 (10)
K1—O21A	2.7664 (10)	O41A—C41A	1.2665 (11)
K1—O42A	2.8555 (11)	O41A—K3^iv	2.6766 (10)
K1—O11A	2.8597 (10)	O41A—K3^xi	2.8124 (13)
K1—N1A	2.8748 (12)	O42A—C41A	1.2579 (12)
K1—N2A	2.9515 (13)	O42A—K3^xi	2.9286 (10)
K1—O1W	2.9840 (11)	N1A—C12A	1.4662 (12)
K1—O11A^i	3.0339 (15)	N1A—C22A	1.4688 (12)
K1—K8	4.0693 (9)	N1A—C1A	1.4707 (13)
K2—O32C	2.709 (9)	N2A—C32A	1.4625 (12)
K2—O2W^ii	2.7098 (13)	N2A—C42A	1.4637 (12)
K2—O21B	2.7452 (11)	N2A—C2A	1.4668 (13)
K2—O42B	2.7474 (14)	C1A—C2A	1.5225 (13)
K2—N2B	2.8092 (10)	C1A—H1A1	0.9900
K2—N1B	2.8616 (10)	C2A—H2A1	0.9900
K2—O11B	2.9625 (12)	C11A—C12A	1.5313 (13)
K2—O71W^iii	3.057 (15)	C12A—H12A	0.9900
K2—O32B	3.076 (4)	C21A—C22A	1.5339 (14)
K2—O6W^ii	3.3299 (13)	C22A—H22A	0.9900
K3—O41A^iv	2.6766 (10)	C31A—C32A	1.5353 (15)
K3—O42B	2.7194 (9)	C32A—H32A	0.9900
K3—O41A^v	2.8124 (13)	C41A—C42A	1.5285 (14)
K3—O42A^v	2.9286 (10)	C42A—H42A	0.9900
K3—O3W	2.9332 (11)	O11B—C11B	1.2413 (12)
K3—O22B	2.9769 (11)	O12B—C11B	1.2874 (12)
K3—O1W^v	3.0778 (12)	O12B—K6^viii	2.7320 (10)
K3—K71^iv	3.886 (15)	O21B—C21B	1.2615 (12)
K3—K3^vi	3.9455 (18)	O21B—K5^ii	2.7210 (11)
K3—K7^iv	4.0012 (12)	O22B—C21B	1.2607 (13)
K4—O4W	2.7353 (10)	O22B—K71^iv	2.38 (2)
K4—O21A^i	2.7465 (10)	O22B—K7^iv	2.6348 (18)
K4—O32A^vii	2.7610 (10)	O22B—K8^v	2.8541 (10)
K4—O31A	2.8269 (13)	O31B—O31C	0.516 (7)
K4—O31A^vii	2.8655 (11)	O31B—C31B	1.251 (2)
K4—O32A	2.9176 (11)	O31B—C31C	1.530 (7)
K4—O6W^viii	3.1637 (12)	O32B—C31C	0.879 (8)
K4—K4^vii	3.6949 (9)	O32B—C31B	1.278 (2)
K4—K6^viii	4.0013 (14)	C31B—O31C	1.116 (6)
K5—O11B	2.6290 (10)	C31B—C32B	1.498 (2)
K5—O21B^ix	2.7210 (11)	C31B—O32C	1.630 (6)
K5—O12A	2.7412 (10)	O31C—C31C	1.271 (8)
K5—O32C	2.757 (7)	O32C—C31C	1.232 (7)
K5—O2W^ii	2.8014 (10)	O41B—C41B	1.2784 (12)
K5—O32B	2.883 (2)	O41B—K7^xv	2.7414 (11)
K5—O7W^i	3.053 (4)	O41B—K71^xv	2.858 (14)
K5—K6	4.2267 (10)	O41B—K8^iii	3.0405 (10)
K5—K8^i	4.4563 (17)	O42B—C41B	1.2507 (12)
K5—K2^ix	4.4600 (11)	N1B—C22B	1.4634 (13)
K6—O31A^x	2.5802 (10)	N1B—C12B	1.4688 (13)
K6—O31C	2.592 (6)	N1B—C1B	1.4714 (12)
K6—O31B	2.686 (2)	N2B—C32B	1.4642 (13)
K6—O6W	2.6962 (14)	N2B—C42B	1.4658 (13)
K6—O12B^x	2.7320 (10)	N2B—C2B	1.4773 (12)
K6—O12A	2.7332 (11)	C1B—C2B	1.5295 (14)
K6—O2W	3.0679 (11)	C1B—H1B1	0.9900
K6—K4^x	4.0013 (14)	C11B—C12B	1.5333 (14)
K8—O7W	2.7937 (15)	C12B—H12C	0.9900
K8—O71W	2.812 (8)	C21B—C22B	1.5386 (14)
K8—O21A	2.8258 (11)	C22B—H22C	0.9900
K8—O22B^xi	2.8541 (10)	C32B—H32C	0.9900
K8—O4W^i	2.8949 (12)	C41B—C42B	1.5324 (14)
K8—O5W	2.9217 (14)	C42B—H42C	0.9900
K8—O1W	2.9320 (11)	O1W—K3^xi	3.0778 (12)
K8—O41B^xii	3.0405 (10)	O1W—H11W	0.8413
K8—O3W^xii	3.1465 (12)	O1W—H12W	0.8419
K8—K71^xiii	3.812 (11)	O2W—K2^ix	2.7098 (13)
K8—K7^xiii	3.8228 (12)	O2W—K5^ix	2.8014 (10)
K7—O22A^viii	2.6283 (13)	O2W—H21W	0.8410
K7—O22B^iv	2.6348 (17)	O2W—H22W	0.8419
K7—O5W^xiii	2.6922 (15)	O3W—K8^iii	3.1465 (12)
K7—O41A	2.7248 (12)	O3W—H31W	0.8408
K7—O41B^xiv	2.7414 (12)	O3W—H32W	0.8420
K7—O8W	2.943 (3)	O4W—K8^i	2.8949 (12)
K7—K8^xiii	3.8228 (12)	O4W—H41W	0.8378
K7—K3^iv	4.0012 (12)	O4W—H42W	0.8389
K7—K3^xi	4.4803 (15)	O5W—K7^xiii	2.6922 (15)
K71—O22B^iv	2.38 (2)	O5W—K71^xiii	2.886 (16)
K71—O41A	2.656 (12)	O5W—H51W	0.8425
K71—O8W	2.764 (14)	O5W—H52W	0.8398
K71—O22A^viii	2.814 (19)	O6W—K4^x	3.1637 (12)
K71—O41B^xiv	2.858 (14)	O6W—K2^ix	3.3299 (13)
K71—O5W^xiii	2.886 (16)	O6W—H61W	0.8395
K71—K8^xiii	3.812 (11)	O6W—H62W	0.8404
K71—K3^iv	3.886 (14)	O7W—O71W	0.607 (13)
O11A—C11A	1.2566 (12)	O7W—K5^i	3.053 (4)
O11A—K1^i	3.0339 (15)	O7W—H71W	0.8297
O12A—C11A	1.2752 (11)	O7W—H72W	0.8373
O21A—C21A	1.2516 (12)	O71W—K2^xii	3.057 (15)
O21A—K4^i	2.7465 (10)	O71W—H71W	0.8741
O22A—C21A	1.2689 (12)	O71W—H72W	0.8482
O22A—K7^x	2.6283 (13)	O8W—H81W	0.8406
O22A—K71^x	2.814 (19)	O8W—H82W	0.8483
O31A—C31A	1.2660 (12)	O9W—H91W	0.8403
O31A—K6^viii	2.5802 (10)	O9W—H92W	0.8401
O31A—K4^vii	2.8655 (11)	O91W—H93W	0.8402
O32A—C31A	1.2548 (12)	O91W—H94W	0.8403
O32A—K1—O21A	171.81 (2)	O5W^xiii—K7—O8W	174.99 (7)
O32A—K1—O42A	93.24 (2)	O41A—K7—O8W	95.13 (7)
O21A—K1—O42A	81.66 (2)	O41B^xiv—K7—O8W	99.41 (6)
O32A—K1—O11A	88.82 (2)	O22B^iv—K71—O41A	87.3 (6)
O21A—K1—O11A	90.64 (2)	O22B^iv—K71—O8W	105.3 (9)
O42A—K1—O11A	137.56 (3)	O41A—K71—O8W	101.1 (5)
O32A—K1—N1A	112.94 (3)	O22B^iv—K71—O22A^viii	171.2 (8)
O21A—K1—N1A	60.10 (2)	O41A—K71—O22A^viii	93.9 (4)
O42A—K1—N1A	81.45 (4)	O8W—K71—O22A^viii	65.9 (3)
O11A—K1—N1A	59.10 (3)	O22B^iv—K71—O41B^xiv	91.8 (4)
O32A—K1—N2A	59.13 (3)	O41A—K71—O41B^xiv	157.3 (7)
O21A—K1—N2A	112.70 (3)	O8W—K71—O41B^xiv	101.0 (4)
O42A—K1—N2A	57.12 (3)	O22A^viii—K71—O41B^xiv	90.5 (6)
O11A—K1—N2A	88.92 (3)	O22B^iv—K71—O5W^xiii	82.3 (3)
N1A—K1—N2A	62.89 (3)	O41A—K71—O5W^xiii	85.0 (4)
O32A—K1—O1W	94.46 (2)	O8W—K71—O5W^xiii	170.3 (9)
O21A—K1—O1W	89.88 (2)	O22A^viii—K71—O5W^xiii	106.5 (8)
O42A—K1—O1W	70.42 (4)	O41B^xiv—K71—O5W^xiii	72.5 (4)
O11A—K1—O1W	151.67 (2)	C11A—O11A—K1	120.81 (6)
N1A—K1—O1W	141.76 (2)	C11A—O11A—K1^i	113.79 (6)
N2A—K1—O1W	116.83 (3)	K1—O11A—K1^i	99.68 (3)
O32A—K1—O11A^i	97.74 (2)	C11A—O12A—K6	114.71 (6)
O21A—K1—O11A^i	90.22 (2)	C11A—O12A—K5	132.58 (6)
O42A—K1—O11A^i	140.87 (3)	K6—O12A—K5	101.08 (3)
O11A—K1—O11A^i	80.32 (3)	C21A—O21A—K4^i	107.77 (6)
N1A—K1—O11A^i	126.80 (3)	C21A—O21A—K1	118.21 (6)
N2A—K1—O11A^i	154.88 (2)	K4^i—O21A—K1	121.10 (3)
O1W—K1—O11A^i	71.36 (3)	C21A—O21A—K8	118.66 (6)
O32C—K2—O2W^ii	79.13 (15)	K4^i—O21A—K8	95.11 (3)
O32C—K2—O21B	166.29 (14)	K1—O21A—K8	93.38 (2)
O2W^ii—K2—O21B	96.79 (2)	C21A—O22A—K7^x	142.53 (6)
O32C—K2—O42B	105.43 (14)	C21A—O22A—K71^x	143.9 (2)
O2W^ii—K2—O42B	150.10 (3)	C31A—O31A—K6^viii	129.61 (6)
O21B—K2—O42B	84.69 (2)	C31A—O31A—K4	88.04 (6)
O32C—K2—N2B	61.83 (15)	K6^viii—O31A—K4	95.36 (3)
O2W^ii—K2—N2B	139.19 (3)	C31A—O31A—K4^vii	86.55 (6)
O21B—K2—N2B	118.24 (3)	K6^viii—O31A—K4^vii	143.69 (3)
O42B—K2—N2B	60.04 (3)	K4—O31A—K4^vii	80.94 (3)
O32C—K2—N1B	112.20 (15)	C31A—O32A—K1	122.73 (6)
O2W^ii—K2—N1B	125.38 (3)	C31A—O32A—K4^vii	91.49 (6)
O21B—K2—N1B	59.50 (3)	K1—O32A—K4^vii	140.74 (3)
O42B—K2—N1B	81.02 (3)	C31A—O32A—K4	84.22 (6)
N2B—K2—N1B	65.74 (3)	K1—O32A—K4	117.77 (3)
O32C—K2—O11B	72.30 (14)	K4^vii—O32A—K4	81.14 (2)
O2W^ii—K2—O11B	79.20 (4)	C41A—O41A—K71	123.7 (2)
O21B—K2—O11B	94.12 (3)	C41A—O41A—K3^iv	138.83 (6)
O42B—K2—O11B	130.61 (3)	K71—O41A—K3^iv	93.5 (3)
N2B—K2—O11B	78.10 (3)	C41A—O41A—K7	123.64 (6)
N1B—K2—O11B	57.23 (3)	K3^iv—O41A—K7	95.59 (3)
O32C—K2—O71W^iii	50.9 (2)	C41A—O41A—K3^xi	87.60 (6)
O2W^ii—K2—O71W^iii	80.59 (17)	K71—O41A—K3^xi	115.1 (5)
O21B—K2—O71W^iii	141.8 (2)	K3^iv—O41A—K3^xi	91.88 (4)
O42B—K2—O71W^iii	80.1 (2)	K7—O41A—K3^xi	108.01 (4)
N2B—K2—O71W^iii	83.46 (15)	C41A—O42A—K1	121.24 (6)
N1B—K2—O71W^iii	148.94 (15)	C41A—O42A—K3^xi	82.64 (6)
O11B—K2—O71W^iii	122.2 (2)	K1—O42A—K3^xi	111.87 (4)
O32C—K2—O32B	3.97 (15)	C12A—N1A—C22A	110.12 (8)
O2W^ii—K2—O32B	82.68 (5)	C12A—N1A—C1A	108.77 (7)
O21B—K2—O32B	165.08 (3)	C22A—N1A—C1A	111.41 (8)
O42B—K2—O32B	103.24 (4)	C12A—N1A—K1	110.16 (6)
N2B—K2—O32B	57.99 (5)	C22A—N1A—K1	103.87 (6)
N1B—K2—O32B	108.74 (4)	C1A—N1A—K1	112.45 (6)
O11B—K2—O32B	71.09 (3)	C32A—N2A—C42A	110.29 (8)
O71W^iii—K2—O32B	52.9 (2)	C32A—N2A—C2A	112.36 (8)
O32C—K2—O6W^ii	117.98 (15)	C42A—N2A—C2A	109.37 (8)
O2W^ii—K2—O6W^ii	80.49 (4)	C32A—N2A—K1	104.90 (6)
O21B—K2—O6W^ii	73.69 (2)	C42A—N2A—K1	108.66 (6)
O42B—K2—O6W^ii	71.24 (3)	C2A—N2A—K1	111.14 (6)
N2B—K2—O6W^ii	127.04 (3)	N1A—C1A—C2A	114.04 (8)
N1B—K2—O6W^ii	127.22 (3)	N2A—C2A—C1A	113.78 (8)
O11B—K2—O6W^ii	154.83 (2)	O11A—C11A—O12A	125.03 (9)
O71W^iii—K2—O6W^ii	68.32 (19)	O11A—C11A—C12A	119.36 (8)
O32B—K2—O6W^ii	120.67 (4)	O12A—C11A—C12A	115.55 (8)
O41A^iv—K3—O42B	89.47 (3)	N1A—C12A—C11A	113.96 (8)
O41A^iv—K3—O41A^v	88.12 (4)	O21A—C21A—O22A	125.00 (9)
O42B—K3—O41A^v	126.41 (3)	O21A—C21A—C22A	119.94 (8)
O41A^iv—K3—O42A^v	107.95 (3)	O22A—C21A—C22A	115.04 (9)
O42B—K3—O42A^v	159.22 (2)	N1A—C22A—C21A	113.48 (8)
O41A^v—K3—O42A^v	45.87 (2)	O32A—C31A—O31A	124.20 (9)
O41A^iv—K3—O3W	130.16 (2)	O32A—C31A—C32A	119.56 (9)
O42B—K3—O3W	63.92 (3)	O31A—C31A—C32A	116.20 (9)
O41A^v—K3—O3W	77.68 (3)	N2A—C32A—C31A	112.87 (8)
O42A^v—K3—O3W	95.66 (3)	O42A—C41A—O41A	125.04 (9)
O41A^iv—K3—O22B	75.85 (3)	O42A—C41A—C42A	118.69 (8)
O42B—K3—O22B	95.59 (3)	O41A—C41A—C42A	116.15 (9)
O41A^v—K3—O22B	135.08 (2)	N2A—C42A—C41A	114.24 (8)
O42A^v—K3—O22B	99.54 (3)	C11B—O11B—K5	133.49 (6)
O3W—K3—O22B	143.22 (3)	C11B—O11B—K2	103.80 (6)
O41A^iv—K3—O1W^v	133.70 (3)	K5—O11B—K2	85.25 (3)
O42B—K3—O1W^v	108.09 (3)	C11B—O12B—K6^viii	134.39 (6)
O41A^v—K3—O1W^v	111.67 (3)	C21B—O21B—K5^ii	134.58 (6)
O42A^v—K3—O1W^v	68.18 (3)	C21B—O21B—K2	113.94 (6)
O3W—K3—O1W^v	95.58 (3)	K5^ii—O21B—K2	109.36 (3)
O22B—K3—O1W^v	60.39 (3)	C21B—O22B—K71^iv	131.2 (5)
O4W—K4—O21A^i	73.65 (4)	C21B—O22B—K7^iv	136.43 (7)
O4W—K4—O32A^vii	157.65 (2)	C21B—O22B—K8^v	133.73 (7)
O21A^i—K4—O32A^vii	123.99 (3)	K71^iv—O22B—K8^v	93.0 (4)
O4W—K4—O31A	83.02 (3)	K7^iv—O22B—K8^v	88.19 (4)
O21A^i—K4—O31A	151.43 (2)	C21B—O22B—K3	91.34 (7)
O32A^vii—K4—O31A	83.04 (3)	K71^iv—O22B—K3	92.3 (3)
O4W—K4—O31A^vii	153.77 (2)	K7^iv—O22B—K3	90.75 (4)
O21A^i—K4—O31A^vii	94.99 (3)	K8^v—O22B—K3	101.29 (3)
O32A^vii—K4—O31A^vii	46.60 (2)	O31C—O31B—C31B	63.0 (7)
O31A—K4—O31A^vii	99.06 (3)	O31C—O31B—C31C	51.1 (7)
O4W—K4—O32A	83.57 (3)	O31C—O31B—K6	74.1 (7)
O21A^i—K4—O32A	114.04 (3)	C31B—O31B—K6	126.39 (14)
O32A^vii—K4—O32A	98.86 (2)	C31C—O31B—K6	116.7 (3)
O31A—K4—O32A	45.60 (3)	C31C—O32B—K5	114.4 (5)
O31A^vii—K4—O32A	79.66 (4)	C31B—O32B—K5	115.72 (12)
O4W—K4—O6W^viii	76.97 (3)	C31C—O32B—K2	114.4 (5)
O21A^i—K4—O6W^viii	109.44 (3)	C31B—O32B—K2	116.16 (11)
O32A^vii—K4—O6W^viii	83.51 (3)	K5—O32B—K2	79.02 (8)
O31A—K4—O6W^viii	80.27 (3)	O31C—C31B—O32B	100.1 (4)
O31A^vii—K4—O6W^viii	129.23 (3)	O31B—C31B—O32B	124.40 (17)
O32A—K4—O6W^viii	124.35 (3)	O31C—C31B—C32B	140.8 (4)
O11B—K5—O21B^ix	162.40 (2)	O31B—C31B—C32B	116.64 (17)
O11B—K5—O12A	90.93 (3)	O32B—C31B—C32B	118.86 (14)
O21B^ix—K5—O12A	95.35 (3)	O31C—C31B—O32C	108.9 (4)
O11B—K5—O32C	76.95 (14)	O31B—C31B—O32C	133.2 (3)
O21B^ix—K5—O32C	117.99 (13)	C32B—C31B—O32C	110.0 (2)
O12A—K5—O32C	99.28 (19)	O31B—O31C—C31B	92.7 (8)
O11B—K5—O2W^ii	83.57 (3)	O31B—O31C—C31C	110.5 (9)
O21B^ix—K5—O2W^ii	90.72 (3)	O31B—O31C—K6	94.9 (8)
O12A—K5—O2W^ii	173.82 (2)	C31B—O31C—K6	146.0 (4)
O32C—K5—O2W^ii	76.78 (19)	C31C—O31C—K6	138.2 (5)
O11B—K5—O32B	79.00 (4)	C31C—O32C—K2	122.8 (5)
O21B^ix—K5—O32B	117.15 (4)	C31B—O32C—K2	121.1 (3)
O12A—K5—O32B	91.45 (7)	C31C—O32C—K5	107.7 (5)
O32C—K5—O32B	8.10 (15)	C31B—O32C—K5	108.7 (3)
O2W^ii—K5—O32B	84.75 (8)	K2—O32C—K5	87.9 (2)
O11B—K5—O7W^i	78.82 (4)	O32B—C31C—O31C	116.3 (7)
O21B^ix—K5—O7W^i	83.60 (3)	O32C—C31C—O31C	128.5 (6)
O12A—K5—O7W^i	108.82 (3)	O32B—C31C—O31B	134.7 (7)
O32C—K5—O7W^i	142.90 (18)	O32C—C31C—O31B	146.9 (7)
O2W^ii—K5—O7W^i	72.94 (3)	O32B—C31C—C32B	132.7 (6)
O32B—K5—O7W^i	150.01 (6)	O32C—C31C—C32B	120.5 (6)
O31A^x—K6—O31C	127.6 (2)	O31C—C31C—C32B	110.9 (5)
O31A^x—K6—O31B	116.63 (9)	O31B—C31C—C32B	92.6 (4)
O31C—K6—O31B	11.03 (17)	C41B—O41B—K7^xv	128.19 (7)
O31A^x—K6—O6W	94.33 (4)	C41B—O41B—K71^xv	123.3 (4)
O31C—K6—O6W	136.9 (2)	C41B—O41B—K8^iii	114.16 (6)
O31B—K6—O6W	147.69 (9)	K7^xv—O41B—K8^iii	82.60 (3)
O31A^x—K6—O12B^x	102.41 (3)	K71^xv—O41B—K8^iii	80.5 (3)
O31C—K6—O12B^x	87.88 (13)	C41B—O42B—K3	137.74 (7)
O31B—K6—O12B^x	89.66 (4)	C41B—O42B—K2	107.02 (6)
O6W—K6—O12B^x	92.58 (3)	K3—O42B—K2	110.30 (3)
O31A^x—K6—O12A	96.74 (3)	C22B—N1B—C12B	110.24 (8)
O31C—K6—O12A	85.87 (13)	C22B—N1B—C1B	112.37 (8)
O31B—K6—O12A	87.89 (4)	C12B—N1B—C1B	111.42 (8)
O6W—K6—O12A	79.01 (2)	C22B—N1B—K2	105.22 (6)
O12B^x—K6—O12A	159.63 (2)	C12B—N1B—K2	107.82 (6)
O31A^x—K6—O2W	159.87 (2)	C1B—N1B—K2	109.48 (6)
O31C—K6—O2W	58.6 (2)	C32B—N2B—C42B	110.58 (8)
O31B—K6—O2W	68.49 (8)	C32B—N2B—C2B	110.38 (8)
O6W—K6—O2W	85.73 (4)	C42B—N2B—C2B	110.67 (8)
O12B^x—K6—O2W	57.52 (2)	C32B—N2B—K2	113.99 (6)
O12A—K6—O2W	103.01 (2)	C42B—N2B—K2	102.57 (6)
O7W—K8—O71W	12.4 (3)	C2B—N2B—K2	108.40 (6)
O7W—K8—O21A	133.66 (3)	N1B—C1B—C2B	113.38 (8)
O71W—K8—O21A	131.74 (19)	N2B—C2B—C1B	113.61 (8)
O7W—K8—O22B^xi	79.95 (5)	O11B—C11B—O12B	124.98 (9)
O71W—K8—O22B^xi	85.8 (2)	O11B—C11B—C12B	120.15 (9)
O21A—K8—O22B^xi	140.46 (3)	O12B—C11B—C12B	114.87 (9)
O7W—K8—O4W^i	64.73 (4)	N1B—C12B—C11B	114.30 (8)
O71W—K8—O4W^i	67.63 (18)	O22B—C21B—O21B	124.26 (10)
O21A—K8—O4W^i	70.09 (4)	O22B—C21B—C22B	115.75 (9)
O22B^xi—K8—O4W^i	128.93 (3)	O21B—C21B—C22B	119.89 (9)
O7W—K8—O5W	148.49 (3)	N1B—C22B—C21B	114.30 (8)
O71W—K8—O5W	144.7 (2)	N2B—C32B—C31B	117.63 (14)
O21A—K8—O5W	77.42 (3)	N2B—C32B—C31C	107.1 (3)
O22B^xi—K8—O5W	74.27 (3)	O42B—C41B—O41B	124.79 (9)
O4W^i—K8—O5W	146.72 (3)	O42B—C41B—C42B	119.96 (9)
O7W—K8—O1W	94.31 (8)	O41B—C41B—C42B	115.24 (8)
O71W—K8—O1W	106.7 (3)	N2B—C42B—C41B	114.69 (8)
O21A—K8—O1W	89.80 (2)	K8—O1W—K1	86.91 (2)
O22B^xi—K8—O1W	63.52 (3)	K8—O1W—K3^xi	97.21 (3)
O4W^i—K8—O1W	82.83 (2)	K1—O1W—K3^xi	104.45 (4)
O5W—K8—O1W	90.21 (3)	H11W—O1W—H12W	105.1
O7W—K8—O41B^xii	88.53 (7)	K2^ix—O2W—K5^ix	87.00 (4)
O71W—K8—O41B^xii	78.7 (3)	K2^ix—O2W—K6	99.73 (4)
O21A—K8—O41B^xii	115.18 (3)	K5^ix—O2W—K6	162.29 (3)
O22B^xi—K8—O41B^xii	79.61 (3)	H21W—O2W—H22W	109.1
O4W^i—K8—O41B^xii	131.51 (3)	K3—O3W—K8^iii	145.68 (3)
O5W—K8—O41B^xii	69.42 (3)	H31W—O3W—H32W	108.5
O1W—K8—O41B^xii	141.79 (2)	K4—O4W—K8^i	93.79 (3)
O7W—K8—O3W^xii	99.35 (8)	H41W—O4W—H42W	108.9
O71W—K8—O3W^xii	87.4 (3)	K7^xiii—O5W—K8	85.73 (4)
O21A—K8—O3W^xii	69.74 (2)	K71^xiii—O5W—K8	82.0 (3)
O22B^xi—K8—O3W^xii	133.87 (3)	H51W—O5W—H52W	106.7
O4W^i—K8—O3W^xii	89.27 (3)	K6—O6W—K4^x	85.74 (3)
O5W—K8—O3W^xii	86.09 (3)	K6—O6W—K2^ix	93.86 (4)
O1W—K8—O3W^xii	159.53 (2)	K4^x—O6W—K2^ix	147.32 (3)
O41B^xii—K8—O3W^xii	54.33 (2)	H61W—O6W—H62W	106.2
O22A^viii—K7—O22B^iv	159.78 (7)	O71W—O7W—K8	85.5 (8)
O22A^viii—K7—O5W^xiii	118.30 (7)	O71W—O7W—K5^i	174.5 (9)
O22B^iv—K7—O5W^xiii	81.78 (4)	K8—O7W—K5^i	99.22 (9)
O22A^viii—K7—O41A	96.62 (3)	H71W—O7W—H72W	99.1
O22B^iv—K7—O41A	81.04 (4)	O7W—O71W—K8	82.1 (9)
O5W^xiii—K7—O41A	87.51 (3)	O7W—O71W—K2^xii	150.8 (10)
O22A^viii—K7—O41B^xiv	97.22 (4)	K8—O71W—K2^xii	127.0 (5)
O22B^iv—K7—O41B^xiv	89.22 (4)	H71W—O71W—H72W	94.8
O5W^xiii—K7—O41B^xiv	77.37 (4)	H81W—O8W—H82W	96.4
O41A—K7—O41B^xiv	163.08 (3)	H91W—O9W—H92W	112.2
O22A^viii—K7—O8W	65.68 (7)	H93W—O91W—H94W	110.8
O22B^iv—K7—O8W	94.41 (8)
C12A—N1A—C1A—C2A	−167.85 (8)	C31B—O32C—C31C—O31C	161 (14)
C22A—N1A—C1A—C2A	70.58 (10)	C31B—O32C—C31C—O31B	161 (15)
C32A—N2A—C2A—C1A	75.84 (10)	C31B—O32C—C31C—C32B	−22 (13)
C42A—N2A—C2A—C1A	−161.34 (8)	O31B—O31C—C31C—O32B	−176.7 (10)
N1A—C1A—C2A—N2A	61.45 (11)	C31B—O31C—C31C—O32B	−175 (2)
C22A—N1A—C12A—C11A	−159.60 (8)	O31B—O31C—C31C—O32C	−179.3 (10)
C1A—N1A—C12A—C11A	78.05 (10)	C31B—O31C—C31C—O32C	−177 (2)
O11A—C11A—C12A—N1A	30.89 (12)	C31B—O31C—C31C—O31B	2.1 (16)
O12A—C11A—C12A—N1A	−151.88 (8)	O31B—O31C—C31C—C32B	3.6 (11)
C12A—N1A—C22A—C21A	66.94 (10)	C31B—O31C—C31C—C32B	5.8 (9)
C1A—N1A—C22A—C21A	−172.28 (8)	O31C—O31B—C31C—O32B	4.1 (12)
O21A—C21A—C22A—N1A	30.00 (12)	C31B—O31B—C31C—O32B	−173 (3)
O22A—C21A—C22A—N1A	−151.11 (8)	O31C—O31B—C31C—O32C	1.0 (14)
C42A—N2A—C32A—C31A	70.67 (10)	C31B—O31B—C31C—O32C	−176 (3)
C2A—N2A—C32A—C31A	−167.02 (8)	C31B—O31B—C31C—O31C	−177 (2)
O32A—C31A—C32A—N2A	27.39 (12)	O31C—O31B—C31C—C32B	−176.6 (10)
O31A—C31A—C32A—N2A	−154.80 (8)	C31B—O31B—C31C—C32B	6.2 (14)
C32A—N2A—C42A—C41A	−159.43 (8)	C22B—N1B—C12B—C11B	−150.39 (8)
C2A—N2A—C42A—C41A	76.53 (10)	C1B—N1B—C12B—C11B	84.13 (10)
O42A—C41A—C42A—N2A	20.68 (12)	O11B—C11B—C12B—N1B	−14.70 (13)
O41A—C41A—C42A—N2A	−163.13 (8)	O12B—C11B—C12B—N1B	165.53 (8)
C31C—O31B—C31B—O31C	2.5 (18)	C12B—N1B—C22B—C21B	74.08 (10)
O31C—O31B—C31B—O32B	1.6 (8)	C1B—N1B—C22B—C21B	−160.98 (8)
C31C—O31B—C31B—O32B	4.1 (16)	O22B—C21B—C22B—N1B	−176.39 (9)
O31C—O31B—C31B—C32B	−174.5 (8)	O21B—C21B—C22B—N1B	7.18 (13)
C31C—O31B—C31B—C32B	−172.1 (18)	C42B—N2B—C32B—C31B	68.35 (15)
O31C—O31B—C31B—O32C	−0.3 (9)	N1B—C1B—C2B—N2B	65.79 (11)
C31C—O31B—C31B—O32C	2.1 (16)	C2B—N2B—C32B—C31B	−168.85 (13)
C31C—O32B—C31B—O31C	−136 (15)	C42B—N2B—C32B—C31C	75.1 (3)
C31C—O32B—C31B—O31B	−137 (15)	C2B—N2B—C32B—C31C	−162.1 (3)
C31C—O32B—C31B—C32B	40 (14)	O31C—C31B—C32B—N2B	−158.5 (5)
C31C—O32B—C31B—O32C	34 (15)	O31B—C31B—C32B—N2B	−154.94 (13)
C31C—O31B—O31C—C31B	−0.7 (5)	O32B—C31B—C32B—N2B	28.7 (2)
C31B—O31B—O31C—C31C	0.7 (5)	O32C—C31B—C32B—N2B	29.5 (3)
O32B—C31B—O31C—O31B	−178.6 (7)	O31C—C31B—C32B—C31C	169.5 (17)
C32B—C31B—O31C—O31B	7.7 (11)	O31B—C31B—C32B—C31C	173.1 (15)
O32C—C31B—O31C—O31B	179.8 (7)	O32B—C31B—C32B—C31C	−3.3 (14)
O31B—C31B—O31C—C31C	−178.0 (15)	O32C—C31B—C32B—C31C	−2.4 (14)
O32B—C31B—O31C—C31C	3.4 (13)	O32B—C31C—C32B—N2B	23.6 (10)
C32B—C31B—O31C—C31C	−170.3 (16)	O32C—C31C—C32B—N2B	25.9 (7)
O32C—C31B—O31C—C31C	1.8 (13)	O31C—C31C—C32B—N2B	−156.8 (5)
O31C—C31B—O32C—C31C	−18 (13)	O31B—C31C—C32B—N2B	−155.7 (2)
O31B—C31B—O32C—C31C	−17 (13)	O32B—C31C—C32B—C31B	174 (2)
O32B—C31B—O32C—C31C	−28 (13)	O32C—C31C—C32B—C31B	176 (2)
C32B—C31B—O32C—C31C	157 (14)	O31C—C31C—C32B—C31B	−6.2 (10)
C31B—O32B—C31C—O32C	−147 (14)	O31B—C31C—C32B—C31B	−5.0 (11)
C31B—O32B—C31C—O31C	42 (14)	C32B—N2B—C42B—C41B	−163.45 (8)
C31B—O32B—C31C—O31B	41 (14)	C2B—N2B—C42B—C41B	73.92 (10)
C31B—O32B—C31C—C32B	−138 (15)	O42B—C41B—C42B—N2B	−1.98 (13)
C31B—O32C—C31C—O32B	150 (14)	O41B—C41B—C42B—N2B	176.88 (8)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) x, −y, z+1/2; (iv) −x+1, y, −z+3/2; (v) x, −y+1, z+1/2; (vi) −x+1, −y+1, −z+2; (vii) −x+1/2, −y+3/2, −z+1; (viii) x, y+1, z; (ix) −x+1/2, y−1/2, −z+3/2; (x) x, y−1, z; (xi) x, −y+1, z−1/2; (xii) x, −y, z−1/2; (xiii) −x+1, −y+1, −z+1; (xiv) −x+1, y+1, −z+3/2; (xv) −x+1, y−1, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O12A^i	0.84	1.85	2.6855 (14)	170
O1W—H12W···O21B^xi	0.84	2.07	2.8854 (13)	163
O1W—H12W···O22B^xi	0.84	2.38	3.0465 (14)	137
O2W—H21W···O12B^x	0.84	1.97	2.8061 (12)	173
O2W—H22W···O32B	0.84	2.06	2.889 (2)	167
O2W—H22W···O31C	0.84	2.11	2.803 (10)	140
O2W—H22W···O32C	0.84	2.28	3.073 (7)	158
O2W—H22W···O31B	0.84	2.59	3.253 (4)	136
O3W—H31W···O41B	0.84	1.99	2.8261 (12)	171
O3W—H31W···O42B	0.84	2.47	2.9975 (13)	121
O3W—H32W···O22A^iii	0.84	1.84	2.6769 (13)	170
O4W—H41W···O11A	0.84	1.93	2.7673 (11)	175
O4W—H42W···O12B	0.84	2.10	2.9237 (14)	169
O5W—H51W···O42A	0.84	1.86	2.7045 (11)	175
O5W—H52W···O41B^iv	0.84	2.05	2.8905 (15)	176
O6W—H61W···O1W^i	0.84	2.13	2.9645 (14)	172
O6W—H62W···O3W^ix	0.84	1.92	2.7506 (15)	170
O7W—H71W···O12B^i	0.83	2.13	2.8991 (15)	153.7
O7W—H72W···O32C^xii	0.84	1.83	2.647 (7)	165.9
O7W—H72W···O32B^xii	0.84	2.00	2.825 (3)	170.1
O71W—H71W···O12B^i	0.87	2.13	2.984 (9)	164.6
O71W—H72W···O32C^xii	0.85	1.83	2.496 (11)	134.6
O71W—H72W···O32B^xii	0.85	2.00	2.733 (9)	144.6
O8W—H82W···O9W	0.85	2.01	2.824 (11)	162
O8W—H81W···O22A^viii	0.84	2.27	3.033 (3)	152
O9W—H91W···O31B^viii	0.84	2.11	2.944 (7)	172
O9W—H92W···O9W^iv	0.84	2.06	2.686 (16)	131
O9W—H92W···O91W^iv	0.84	2.24	2.996 (15)	150
O91W—H94W···O31B^viii	0.84	2.18	2.936 (7)	149
O91W—H93W···O9W^iv	0.84	2.46	2.996 (15)	123
C12A—H12B···O31A^x	0.99	2.54	3.3905 (15)	144
C22A—H22A···O8W^x	0.99	2.56	3.410 (3)	144
C42A—H42A···O8W	0.99	2.49	3.321 (3)	141
C42A—H42B···O22A^viii	0.99	2.58	3.3954 (15)	139
C2B—H2B2···O42B	0.99	2.49	3.0675 (15)	117

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (iii) x, −y, z+1/2; (iv) −x+1, y, −z+3/2; (viii) x, y+1, z; (ix) −x+1/2, y−1/2, −z+3/2; (x) x, y−1, z; (xi) x, −y+1, z−1/2; (xii) x, −y, z−1/2.