Poly[μ2-acetato-diacetonitrile[μ2-N,N′-bis­(2-hydroxy­phen­yl)pyridine-2,6-dicarboxamide]potassium(I)]

Pérez, Y.; Johnson, A.L.; Raithby, P.R.

doi:10.1107/S1600536806033678

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 9| September 2006| Pages m2359-m2360

https://doi.org/10.1107/S1600536806033678

Poly[μ₂-acetato-diacetonitrile[μ₂-N,N′-bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide]potassium(I)]

Yolanda Pérez,^a Andrew L. Johnson ^b and Paul R. Raithby ^b,^c ^*

^aDepartamento de Química Inorgánica y Analítica, ESCET, Universidad Rey Juan Carlos, 28933 Móstoles (Madrid), Spain, ^bDepartment of Chemistry, University of Bath, Bath BA2 7AY, England, and ^cCCLRC Daresbury Laboratory, Daresbury, Warrington WA4 4AD, England
^*Correspondence e-mail: p.r.raithby@bath.ac.uk

(Received 18 August 2006; accepted 22 August 2006; online 31 August 2006)

The title compound, [K(C₂H₃O₂)(C₂H₃N)₂(C₁₉H₁₅N₃O₄)], is polymeric. Each K⁺ ion adopts a distorted octahedral geometry, being linked to two 2,6-pyridinedicarboxamide ligands through carbonyl O atoms and to two acetate groups also through O atoms. The potassium coordination is completed by the N atoms of two acetonitrile ligands. The 2,6-pyridinedicarboxamide ligands are also involved in O—H⋯O hydrogen bonds.

Comment

Many derivatives of 2,6-pyridinecarboxamide show anti-inflammatory, antipyretic and analgesic activities (Singha & Sathyanarayana, 1997 , and references therein). A series of Cu^II, Fe^III, Co^III and Ni^II (Chavez et al., 1996 , 1998 ; Marlin et al., 1999 ; Hiratani & Taguchi, 1990 ) complexes containing 2,6-pyridinedicarboxamide ligands has been synthesized during the last two decades. The derivative N,N′-bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide has been synthesized previously (Marlin et al., 2000 ). Several complexes of this ligand have been reported, two of which consist of the fully deprotonated pentadentate ligand with an Fe^III atom in the equatorial plane of the ligand, the coordination being completed by two monodentate ligands in axial sites (Marlin et al., 2000). We are continuing to investigate the coordination properties of this ligand with a range of heavier main group and transition metals.

In this paper, we report the synthesis and crystal structure of the title polymeric potassium complex of N,N′-bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide, (I) (Fig. 1), where the ligand links two K⁺ ions through the two carbonyl groups. The coordination environment of each K⁺ centre is completed by coordination of one O atom of each of two acetate groups, and two terminal acetonitrile ligands. The acetate groups act as linker groups between adjacent K⁺ centres.

The K⁺ centres display a distorted octahedral coordination geometry. The two K—O(carbonyl) distances (average 2.75 Å) are similar in length to the two K—O(acetate) distances (average 2.72 Å), and these four distances are significantly shorter than the two K—N(acetonitrile) distances (average 3.11 Å). The K—O(ethoxy) distances are similar to the average value of 2.67 Å previously reported for an ethanol-solvated dimeric potassium calixarene complex (Clague et al., 1999 ).

In addition, the N,N′-bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide ligands are involved in O—H⋯O hydrogen bonds from the two hydroxyl groups to the linking acetate groups (Table 1).

Figure 1
A view of (I), with 50% probability displacement ellipsoids, showing the polymeric nature of the structure. [Symmetry codes: (i) $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, 1 − z; (ii) x − $[{1\over 2}]$ , y, $[{1\over 2}]$ − z; (iii) $[{1\over 2}]$ − x, $[{3\over 2}]$ − y, 1 − z; (iv) $[{1\over 2}]$ + x, y, $[{1\over 2}]$ − z; (v) $[{1\over 2}]$ − x, 1 − y, $[{1\over 2}]$ + z; (vi) $[{1\over 2}]$ − x, 1 − y, $[{1\over 2}]$ + z; (vii) −x, 1 − y, 1 − z.]

Experimental

Compound (I) was synthesized by mixing solutions of N,N′-bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide and KO^tBu, in the presence of potassium acetate (as a potential deprotonation reagent), in acetonitrile, in a 1:2 molar ratio, and stirring the resulting mixture for 2 h. Orange needles of (I) suitable for X-ray analysis were grown by slow diffusion of ethyl acetate into a dimethylformamide solution of (I).

Crystal data

[K(C₂H₃O₂)(C₂H₃N)₂(C₁₉H₁₅N₃O₄)]
M_r = 529.59
Orthorhombic, P b c a
a = 13.6100 (2) Å
b = 21.1060 (3) Å
c = 17.5730 (3) Å
V = 5047.89 (13) Å³
Z = 8
D_x = 1.394 Mg m⁻³
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 150 (2) K
Block, orange
0.17 × 0.13 × 0.1 mm

Data collection

Bruker NoniusKappa CCD area-detector diffractometer
ω and φ scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.919, T_max = 0.974
30810 measured reflections
4445 independent reflections
3751 reflections with I > 2σ(I)
R_int = 0.046
θ_max = 25.0°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.183
S = 1.05
4445 reflections
339 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0943P)² + 9.313P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.006
Δρ_max = 0.45 e Å⁻³
Δρ_min = −1.04 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O6ⁱ	0.84	1.8	2.638 (3)	174
O1—H1O⋯O5ⁱ	0.84	1.78	2.618 (3)	175
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

H atoms were constrained as riding atoms, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for aromatic H, and C—H =0.98 Å and U_iso(H) = 1.5U_eq(C) for methyl H, and with N—H = 0.88 Å and U_iso(H) = 1.2U_eq(N), and O—H = 0.84 Å and U_iso(H) = 1.2U_eq(O). There was no residual electron density above 0.5 e Å³. The deepest hole is located 0.45 Å from atom K1.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806033678/ng2075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806033678/ng2075Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Poly[diacetonitrile-µ₂-acetato-µ₂-N,N'-bis(2-hydroxyphenyl)pyridine- 2,6-dicarboxamide)potassium(I)] top

Crystal data top

[K(C₂H₃O₂)(C₂H₃N)₂(C₁₉H₁₅N₃O₄)]	D_x = 1.394 Mg m⁻³
M_r = 529.59	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 48840 reflections
a = 13.6100 (2) Å	θ = 2.9–25.0°
b = 21.1060 (3) Å	µ = 0.26 mm⁻¹
c = 17.5730 (3) Å	T = 150 K
V = 5047.89 (13) Å³	Block, orange
Z = 8	0.17 × 0.13 × 0.1 mm
F(000) = 2208

Data collection top

Bruker NoniusKappa CCD area-detector diffractometer	3751 reflections with I > 2σ(I)
ω and φ scans	R_int = 0.046
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	θ_max = 25.0°, θ_min = 3.6°
T_min = 0.919, T_max = 0.974	h = −16→14
30810 measured reflections	k = −25→24
4445 independent reflections	l = −20→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.062	w = 1/[σ²(F_o²) + (0.0943P)² + 9.313P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.183	(Δ/σ)_max = 0.006
S = 1.05	Δρ_max = 0.45 e Å⁻³
4445 reflections	Δρ_min = −1.04 e Å⁻³
339 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
K1	0.32899 (6)	0.63984 (4)	0.32048 (5)	0.0393 (3)
O1	0.03601 (16)	0.46047 (10)	0.61597 (12)	0.0260 (5)
H1O	0.0245	0.4377	0.6542	0.031*
O2	0.21897 (17)	0.59656 (12)	0.44330 (14)	0.0370 (6)
O3	−0.18735 (16)	0.74268 (10)	0.61676 (13)	0.0277 (5)
O4	−0.14184 (15)	0.52344 (10)	0.69281 (13)	0.0268 (5)
H4O	−0.1462	0.4862	0.7094	0.032*
O5	0.49403 (15)	0.60471 (10)	0.24059 (12)	0.0265 (5)
O6	0.65655 (16)	0.59633 (10)	0.23424 (13)	0.0294 (5)
N1	0.00694 (18)	0.64723 (11)	0.54463 (13)	0.0203 (5)
N2	0.11790 (19)	0.54268 (12)	0.52490 (14)	0.0233 (6)
H2N	0.0635	0.5472	0.5514	0.028*
N3	−0.14907 (18)	0.63872 (11)	0.63950 (14)	0.0212 (6)
H3N	−0.1019	0.6108	0.633	0.025*
N4	0.3715 (3)	0.7545 (2)	0.2052 (2)	0.0638 (11)
N5	0.4598 (3)	0.58325 (18)	0.4408 (2)	0.0512 (9)
C1	0.1195 (2)	0.44041 (14)	0.58171 (16)	0.0230 (7)
C2	0.1607 (2)	0.38097 (16)	0.59291 (19)	0.0294 (7)
H2	0.1313	0.3521	0.6276	0.035*
C3	0.2448 (3)	0.36378 (16)	0.55337 (19)	0.0337 (8)
H3	0.2729	0.3231	0.561	0.04*
C4	0.2878 (3)	0.40571 (17)	0.5028 (2)	0.0353 (8)
H4	0.3452	0.3934	0.4758	0.042*
C5	0.2486 (2)	0.46531 (17)	0.49105 (18)	0.0299 (7)
H5	0.2788	0.4939	0.4564	0.036*
C6	0.1638 (2)	0.48308 (15)	0.53076 (17)	0.0237 (7)
C7	0.1456 (2)	0.59359 (15)	0.48446 (17)	0.0245 (7)
C8	0.0810 (2)	0.65075 (15)	0.49447 (17)	0.0233 (7)
C9	0.1018 (2)	0.70516 (16)	0.45264 (19)	0.0307 (7)
H9	0.1543	0.7056	0.417	0.037*
C10	0.0446 (3)	0.75849 (16)	0.46388 (19)	0.0321 (8)
H10	0.0575	0.7963	0.4364	0.038*
C11	−0.0316 (2)	0.75581 (15)	0.51580 (18)	0.0264 (7)
H11	−0.0716	0.7919	0.5251	0.032*
C12	−0.0483 (2)	0.69926 (13)	0.55413 (16)	0.0203 (6)
C13	−0.1347 (2)	0.69564 (13)	0.60721 (16)	0.0209 (6)
C14	−0.2309 (2)	0.61816 (14)	0.68278 (16)	0.0204 (6)
C15	−0.3139 (2)	0.65442 (15)	0.69736 (18)	0.0256 (7)
H15	−0.3174	0.6969	0.6796	0.031*
C16	−0.3917 (2)	0.62870 (16)	0.73790 (19)	0.0290 (7)
H16	−0.4486	0.6535	0.7474	0.035*
C17	−0.3868 (2)	0.56729 (15)	0.76450 (18)	0.0287 (7)
H17	−0.4403	0.5499	0.7923	0.034*
C18	−0.3037 (2)	0.53074 (15)	0.75074 (18)	0.0255 (7)
H18	−0.3002	0.4886	0.7697	0.031*
C19	−0.2254 (2)	0.55555 (14)	0.70935 (16)	0.0216 (6)
C20	0.5794 (2)	0.62540 (14)	0.25225 (17)	0.0223 (7)
C21	0.5892 (3)	0.68904 (15)	0.2908 (2)	0.0349 (8)
H21A	0.5745	0.6846	0.3451	0.052*
H21B	0.5429	0.7191	0.2678	0.052*
H21C	0.6564	0.7048	0.2844	0.052*
C22	0.3376 (3)	0.79010 (18)	0.1655 (2)	0.0359 (8)
C23	0.2917 (4)	0.8356 (2)	0.1151 (3)	0.0617 (13)
H23A	0.2528	0.8131	0.0767	0.092*
H23B	0.3425	0.861	0.0899	0.092*
H23C	0.2486	0.8635	0.1446	0.092*
C24	0.5035 (3)	0.5437 (2)	0.4138 (2)	0.0417 (9)
C25	0.5612 (4)	0.4924 (2)	0.3796 (2)	0.0561 (11)
H25A	0.6299	0.5058	0.3748	0.084*
H25B	0.5349	0.4824	0.3291	0.084*
H25C	0.5575	0.4547	0.4121	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0324 (5)	0.0411 (5)	0.0445 (5)	−0.0007 (3)	0.0030 (3)	−0.0026 (3)
O1	0.0257 (11)	0.0253 (11)	0.0269 (11)	0.0016 (9)	0.0042 (9)	0.0048 (9)
O2	0.0299 (13)	0.0408 (14)	0.0402 (14)	−0.0016 (11)	0.0153 (11)	0.0023 (11)
O3	0.0285 (12)	0.0220 (11)	0.0326 (12)	0.0049 (9)	0.0016 (10)	0.0015 (9)
O4	0.0223 (11)	0.0207 (11)	0.0374 (13)	0.0026 (9)	0.0038 (10)	0.0068 (10)
O5	0.0198 (11)	0.0289 (11)	0.0306 (12)	−0.0021 (9)	0.0029 (9)	−0.0063 (9)
O6	0.0211 (11)	0.0257 (11)	0.0413 (14)	−0.0006 (9)	0.0036 (10)	−0.0047 (10)
N1	0.0186 (12)	0.0228 (12)	0.0195 (12)	−0.0044 (10)	−0.0023 (10)	0.0002 (10)
N2	0.0200 (13)	0.0274 (14)	0.0227 (13)	0.0018 (11)	0.0021 (10)	−0.0004 (10)
N3	0.0189 (12)	0.0194 (12)	0.0253 (13)	0.0027 (10)	0.0029 (10)	0.0023 (10)
N4	0.081 (3)	0.065 (2)	0.045 (2)	0.039 (2)	−0.007 (2)	−0.0071 (19)
N5	0.0345 (18)	0.049 (2)	0.070 (2)	0.0018 (17)	−0.0036 (18)	0.0115 (19)
C1	0.0216 (15)	0.0265 (16)	0.0210 (15)	0.0015 (13)	−0.0064 (12)	−0.0042 (12)
C2	0.0325 (18)	0.0269 (16)	0.0289 (17)	0.0026 (14)	−0.0092 (14)	−0.0035 (14)
C3	0.0335 (18)	0.0325 (18)	0.0352 (18)	0.0119 (15)	−0.0115 (16)	−0.0093 (15)
C4	0.0273 (17)	0.045 (2)	0.0340 (18)	0.0117 (16)	−0.0036 (15)	−0.0141 (16)
C5	0.0238 (16)	0.0391 (19)	0.0266 (16)	0.0029 (14)	−0.0017 (14)	−0.0069 (14)
C6	0.0207 (15)	0.0279 (16)	0.0225 (15)	0.0031 (13)	−0.0052 (12)	−0.0054 (12)
C7	0.0234 (16)	0.0295 (17)	0.0206 (15)	−0.0032 (13)	−0.0018 (13)	−0.0015 (13)
C8	0.0206 (15)	0.0272 (16)	0.0220 (15)	−0.0053 (13)	−0.0024 (12)	0.0000 (12)
C9	0.0269 (17)	0.0340 (18)	0.0313 (17)	−0.0056 (14)	0.0053 (14)	0.0057 (14)
C10	0.0366 (19)	0.0261 (17)	0.0335 (18)	−0.0095 (15)	0.0028 (15)	0.0072 (14)
C11	0.0299 (17)	0.0209 (15)	0.0285 (16)	−0.0043 (13)	−0.0028 (14)	0.0008 (13)
C12	0.0192 (14)	0.0218 (15)	0.0198 (14)	−0.0049 (12)	−0.0054 (12)	−0.0001 (12)
C13	0.0212 (15)	0.0215 (15)	0.0201 (14)	−0.0002 (12)	−0.0049 (12)	0.0004 (12)
C14	0.0190 (15)	0.0224 (14)	0.0197 (14)	−0.0021 (12)	0.0002 (11)	−0.0002 (12)
C15	0.0249 (16)	0.0239 (16)	0.0280 (16)	0.0036 (13)	0.0001 (13)	0.0016 (13)
C16	0.0204 (16)	0.0327 (17)	0.0340 (18)	0.0048 (13)	0.0037 (14)	−0.0020 (14)
C17	0.0227 (16)	0.0339 (17)	0.0295 (17)	−0.0051 (14)	0.0037 (13)	−0.0004 (14)
C18	0.0265 (16)	0.0222 (15)	0.0276 (15)	−0.0028 (13)	0.0012 (13)	0.0015 (13)
C19	0.0201 (15)	0.0241 (15)	0.0205 (15)	0.0000 (12)	−0.0009 (12)	−0.0017 (12)
C20	0.0244 (17)	0.0212 (15)	0.0212 (15)	0.0003 (13)	0.0029 (12)	−0.0010 (12)
C21	0.0324 (19)	0.0246 (17)	0.048 (2)	0.0021 (14)	−0.0034 (16)	−0.0084 (15)
C22	0.037 (2)	0.0362 (19)	0.0347 (19)	0.0065 (16)	−0.0003 (16)	−0.0090 (16)
C23	0.087 (4)	0.051 (3)	0.047 (2)	0.023 (3)	0.000 (2)	0.007 (2)
C24	0.039 (2)	0.047 (2)	0.039 (2)	−0.0073 (19)	−0.0100 (17)	0.0143 (18)
C25	0.070 (3)	0.062 (3)	0.037 (2)	0.008 (2)	−0.005 (2)	−0.003 (2)

Geometric parameters (Å, º) top

K1—O6ⁱ	2.697 (2)	C5—C6	1.400 (5)
K1—O3ⁱⁱ	2.723 (2)	C5—H5	0.95
K1—O5	2.751 (2)	C7—C8	1.503 (4)
K1—O2	2.781 (2)	C8—C9	1.392 (4)
K1—N5	3.011 (4)	C9—C10	1.382 (5)
K1—N4	3.209 (4)	C9—H9	0.95
O1—C1	1.354 (4)	C10—C11	1.383 (5)
O1—H1O	0.84	C10—H10	0.95
O2—C7	1.234 (4)	C11—C12	1.389 (4)
O3—C13	1.236 (4)	C11—H11	0.95
O3—K1ⁱⁱⁱ	2.723 (2)	C12—C13	1.503 (4)
O4—C19	1.356 (4)	C14—C15	1.388 (4)
O4—H4O	0.84	C14—C19	1.404 (4)
O5—C20	1.258 (4)	C15—C16	1.387 (5)
O6—C20	1.257 (4)	C15—H15	0.95
O6—K1^iv	2.697 (2)	C16—C17	1.379 (5)
N1—C8	1.341 (4)	C16—H16	0.95
N1—C12	1.341 (4)	C17—C18	1.391 (5)
N2—C7	1.342 (4)	C17—H17	0.95
N2—C6	1.408 (4)	C18—C19	1.392 (4)
N2—H2N	0.88	C18—H18	0.95
N3—C13	1.343 (4)	C20—C21	1.510 (4)
N3—C14	1.417 (4)	C21—H21A	0.98
N3—H3N	0.88	C21—H21B	0.98
N4—C22	1.123 (5)	C21—H21C	0.98
N5—C24	1.129 (5)	C22—C23	1.449 (6)
C1—C2	1.388 (4)	C23—H23A	0.98
C1—C6	1.406 (5)	C23—H23B	0.98
C2—C3	1.387 (5)	C23—H23C	0.98
C2—H2	0.95	C24—C25	1.467 (6)
C3—C4	1.384 (5)	C25—H25A	0.98
C3—H3	0.95	C25—H25B	0.98
C4—C5	1.382 (5)	C25—H25C	0.98
C4—H4	0.95

O6ⁱ—K1—O3ⁱⁱ	112.54 (7)	C10—C9—H9	120.6
O6ⁱ—K1—O5	115.90 (7)	C8—C9—H9	120.6
O3ⁱⁱ—K1—O5	121.26 (7)	C9—C10—C11	118.9 (3)
O6ⁱ—K1—O2	72.33 (8)	C9—C10—H10	120.6
O3ⁱⁱ—K1—O2	86.60 (7)	C11—C10—H10	120.6
O5—K1—O2	138.35 (7)	C10—C11—C12	118.6 (3)
O6ⁱ—K1—N5	129.03 (9)	C10—C11—H11	120.7
O3ⁱⁱ—K1—N5	97.19 (9)	C12—C11—H11	120.7
O5—K1—N5	76.62 (9)	N1—C12—C11	123.4 (3)
O2—K1—N5	69.09 (9)	N1—C12—C13	118.3 (2)
O6ⁱ—K1—N4	100.86 (10)	C11—C12—C13	118.2 (3)
O3ⁱⁱ—K1—N4	65.38 (8)	O3—C13—N3	125.2 (3)
O5—K1—N4	74.58 (8)	O3—C13—C12	119.8 (3)
O2—K1—N4	146.57 (9)	N3—C13—C12	114.9 (3)
N5—K1—N4	129.49 (11)	C15—C14—C19	120.1 (3)
C1—O1—H1O	109.5	C15—C14—N3	124.7 (3)
C7—O2—K1	155.1 (2)	C19—C14—N3	115.1 (3)
C13—O3—K1ⁱⁱⁱ	137.67 (19)	C14—C15—C16	120.0 (3)
C19—O4—H4O	109.5	C14—C15—H15	120
C20—O5—K1	125.27 (18)	C16—C15—H15	120
C20—O6—K1^iv	130.59 (19)	C17—C16—C15	120.4 (3)
C8—N1—C12	117.3 (3)	C17—C16—H16	119.8
C7—N2—C6	129.0 (3)	C15—C16—H16	119.8
C7—N2—H2N	115.5	C16—C17—C18	120.1 (3)
C6—N2—H2N	115.5	C16—C17—H17	120
C13—N3—C14	128.0 (3)	C18—C17—H17	120
C13—N3—H3N	116	C17—C18—C19	120.3 (3)
C14—N3—H3N	116	C17—C18—H18	119.8
C22—N4—K1	145.3 (4)	C19—C18—H18	119.8
C24—N5—K1	108.0 (3)	O4—C19—C18	124.5 (3)
O1—C1—C2	124.0 (3)	O4—C19—C14	116.4 (3)
O1—C1—C6	116.3 (3)	C18—C19—C14	119.2 (3)
C2—C1—C6	119.8 (3)	O6—C20—O5	124.1 (3)
C3—C2—C1	119.9 (3)	O6—C20—C21	118.3 (3)
C3—C2—H2	120	O5—C20—C21	117.6 (3)
C1—C2—H2	120	C20—C21—H21A	109.5
C4—C3—C2	120.2 (3)	C20—C21—H21B	109.5
C4—C3—H3	119.9	H21A—C21—H21B	109.5
C2—C3—H3	119.9	C20—C21—H21C	109.5
C5—C4—C3	121.0 (3)	H21A—C21—H21C	109.5
C5—C4—H4	119.5	H21B—C21—H21C	109.5
C3—C4—H4	119.5	N4—C22—C23	178.6 (5)
C4—C5—C6	119.2 (3)	C22—C23—H23A	109.5
C4—C5—H5	120.4	C22—C23—H23B	109.5
C6—C5—H5	120.4	H23A—C23—H23B	109.5
C5—C6—C1	120.0 (3)	C22—C23—H23C	109.5
C5—C6—N2	124.6 (3)	H23A—C23—H23C	109.5
C1—C6—N2	115.4 (3)	H23B—C23—H23C	109.5
O2—C7—N2	125.3 (3)	N5—C24—C25	179.2 (5)
O2—C7—C8	120.1 (3)	C24—C25—H25A	109.5
N2—C7—C8	114.6 (3)	C24—C25—H25B	109.5
N1—C8—C9	123.0 (3)	H25A—C25—H25B	109.5
N1—C8—C7	118.2 (3)	C24—C25—H25C	109.5
C9—C8—C7	118.8 (3)	H25A—C25—H25C	109.5
C10—C9—C8	118.8 (3)	H25B—C25—H25C	109.5

O6ⁱ—K1—O2—C7	−53.9 (5)	C12—N1—C8—C7	178.4 (2)
O3ⁱⁱ—K1—O2—C7	61.1 (5)	O2—C7—C8—N1	−174.4 (3)
O5—K1—O2—C7	−163.2 (5)	N2—C7—C8—N1	3.6 (4)
N5—K1—O2—C7	160.1 (5)	O2—C7—C8—C9	4.3 (4)
N4—K1—O2—C7	29.0 (6)	N2—C7—C8—C9	−177.6 (3)
O6ⁱ—K1—O5—C20	172.2 (2)	N1—C8—C9—C10	1.0 (5)
O3ⁱⁱ—K1—O5—C20	29.7 (3)	C7—C8—C9—C10	−177.6 (3)
O2—K1—O5—C20	−95.6 (2)	C8—C9—C10—C11	−0.5 (5)
N5—K1—O5—C20	−60.7 (2)	C9—C10—C11—C12	−0.7 (5)
N4—K1—O5—C20	77.4 (2)	C8—N1—C12—C11	−0.9 (4)
O6ⁱ—K1—N4—C22	25.3 (5)	C8—N1—C12—C13	177.1 (2)
O3ⁱⁱ—K1—N4—C22	−84.7 (5)	C10—C11—C12—N1	1.4 (5)
O5—K1—N4—C22	139.4 (5)	C10—C11—C12—C13	−176.7 (3)
O2—K1—N4—C22	−49.0 (6)	K1ⁱⁱⁱ—O3—C13—N3	114.6 (3)
N5—K1—N4—C22	−163.2 (5)	K1ⁱⁱⁱ—O3—C13—C12	−67.2 (4)
O6ⁱ—K1—N5—C24	79.2 (3)	C14—N3—C13—O3	8.1 (5)
O3ⁱⁱ—K1—N5—C24	−153.9 (3)	C14—N3—C13—C12	−170.2 (3)
O5—K1—N5—C24	−33.4 (3)	N1—C12—C13—O3	−179.6 (3)
O2—K1—N5—C24	122.5 (3)	C11—C12—C13—O3	−1.4 (4)
N4—K1—N5—C24	−90.1 (3)	N1—C12—C13—N3	−1.2 (4)
O1—C1—C2—C3	177.9 (3)	C11—C12—C13—N3	177.0 (3)
C6—C1—C2—C3	−0.5 (4)	C13—N3—C14—C15	2.1 (5)
C1—C2—C3—C4	0.1 (5)	C13—N3—C14—C19	179.9 (3)
C2—C3—C4—C5	0.4 (5)	C19—C14—C15—C16	−0.3 (5)
C3—C4—C5—C6	−0.3 (5)	N3—C14—C15—C16	177.4 (3)
C4—C5—C6—C1	−0.2 (4)	C14—C15—C16—C17	0.6 (5)
C4—C5—C6—N2	178.7 (3)	C15—C16—C17—C18	0.0 (5)
O1—C1—C6—C5	−177.9 (3)	C16—C17—C18—C19	−0.8 (5)
C2—C1—C6—C5	0.6 (4)	C17—C18—C19—O4	−179.6 (3)
O1—C1—C6—N2	3.1 (4)	C17—C18—C19—C14	1.0 (5)
C2—C1—C6—N2	−178.4 (3)	C15—C14—C19—O4	−179.9 (3)
C7—N2—C6—C5	−2.6 (5)	N3—C14—C19—O4	2.2 (4)
C7—N2—C6—C1	176.3 (3)	C15—C14—C19—C18	−0.5 (4)
K1—O2—C7—N2	151.0 (4)	N3—C14—C19—C18	−178.4 (3)
K1—O2—C7—C8	−31.2 (7)	K1^iv—O6—C20—O5	142.5 (2)
C6—N2—C7—O2	0.7 (5)	K1^iv—O6—C20—C21	−37.9 (4)
C6—N2—C7—C8	−177.3 (3)	K1—O5—C20—O6	156.2 (2)
C12—N1—C8—C9	−0.3 (4)	K1—O5—C20—C21	−23.4 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O6^v	0.84	1.8	2.638 (3)	174
O1—H1O···O5^v	0.84	1.78	2.618 (3)	175

Symmetry code: (v) −x+1/2, −y+1, z+1/2.

Acknowledgements

The authors are grateful to the EPSRC, the Nuffield Foundation and the Universidad Rey Juan Carlos for funding.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Chavez, F. A., Olmstead, M. M. & Mascharak, P. K. (1996). Inorg. Chem. 35, 1410–1412. CSD CrossRef PubMed CAS Web of Science Google Scholar
Chavez, F. A., Olmstead, M. M. & Mascharak, P. K. (1998). Inorg. Chim. Acta, 269, 269–273. Web of Science CSD CrossRef CAS Google Scholar
Clague, N. P., Clegg, W., Coles, S. J., Crane, J. D., Moreton, D. J., Sinn, E., Teat, S. J. & Young, N. A. (1999). Chem. Commun. pp. 379–380. CrossRef Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hiratani, K. & Taguchi, K. (1990). Bull. Chem. Soc. Jpn, 63, 3331–3333. CrossRef CAS Web of Science Google Scholar
Marlin, D. S., Olmstead, M. M. & Mascharak, P. K. (1999). Inorg. Chem. 38, 3258–3260. Web of Science CSD CrossRef CAS Google Scholar
Marlin, D. S., Olmstead, M. M. & Mascharak, P. K. (2000). Inorg. Chim. Acta, 297, 106–114. Web of Science CSD CrossRef CAS Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Singha, N. C. & Sathyanarayana, D. N. (1997). J. Mol. Struct. 403, 123–135. CrossRef CAS Web of Science Google Scholar

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Volume 62| Part 9| September 2006| Pages m2359-m2360

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