(18-Crown-6-κ6O)(pyrazolato-κ2N,N′)-potassium(I)

Kunz, K.; Lerner, H.-W.; Bolte, M.

doi:10.1107/S1600536808043237

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m171

doi:10.1107/S1600536808043237

Open

access

(18-Crown-6-κ⁶O)(pyrazolato-κ²N,N′)-potassium(I)

Kerstin Kunz,^a Hans-Wolfram Lerner ^a and Michael Bolte ^a ^*

^aInstitut für Anorganische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 11 December 2008; accepted 18 December 2008; online 10 January 2009)

The asymmetric unit of the title compound, [K(C₃H₃N₂)(C₁₂H₂₄O₆)], is composed of a potassium cation bonded to the six O atoms of a crown ether molecule and the two N atoms of a pyrazolate anion. The K⋯O distances range from 2.8416 (8) to 3.0025 (8) Å, and the two K⋯N distances are 2.7441 (11) and 2.7654 (11) Å. The K cation is displaced by 0.8437 (4) Å from the best plane through the six O atoms. The latter plane is almost perpendicular to the plane of the pyrazolate ring [dihedral angle 83.93 (3)°].

Related literature

For related literature on scorpionate complexes, see: Bieller et al. (2006 ); Morawitz et al. (2008 ); Trofimenko (1993 ).

Experimental

Crystal data

[K(C₃H₃N₂)(C₁₂H₂₄O₆)]
M_r = 370.49
Monoclinic, P 2₁ /n
a = 11.5330 (6) Å
b = 8.2369 (5) Å
c = 20.7622 (10) Å
β = 101.612 (4)°
V = 1931.96 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 173 (2) K
0.25 × 0.12 × 0.12 mm

Data collection

STOE IPDS II two-circle-diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ; Blessing, 1995 ) T_min = 0.919, T_max = 0.966
23118 measured reflections
3602 independent reflections
3234 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.066
S = 1.03
3602 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043237/rz2281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043237/rz2281Isup2.hkl

checkCIF report

Comment top

We report here the X-ray crystal structure analysis of the potassium pyrazolide as complex with 18-crown-6, [K(18-crown-6)(C₃H₃N₂)] or [K(18-crown-6)(pz)]. Following the first synthesis of a scorpionate complex, considerable progress has been made towards extending this area of chemistry (Trofimenko, 1993). Our studies have shown that an important factor influencing the stability of scorpionates appears to be the degree of steric crowding around the boron centre. The results of investigations in our group show that the scorpionates RB(3–R'pz)₃^- and RB(4–R'pz)₃^- decompose in the presence of transition metal salts much more easily when R and R' are bulky (Bieller et al., 2006; Morawitz et al., 2008). Now we have found that irradiation of Mn(C₅H₃)(Bpz₃)₂(THF)₂ (I) in the presence of 18-crown-6 leads to the formation of potassium pyrazolide (II).

The asymmetric unit of the title compound, [C₁₂H₂₄O₆]K⁺[C₃H₃N₂]^-, is composed of a potassium cation bonded to the six O atoms of a crown ether molecule and the two N atoms of a pyrazolate anion. The K···O distances range from 2.8416 (8) Å to 3.0025 (8) Å, and the two K···N distances are 2.7441 (11) Å and 2.7654 (11) Å. The K cation is displaced by 0.8437 (4) Å from the best plane through the six O atoms. The latter plane is almost perpendicular to the plane of the pyrazolate ring [dihedral angle 83.93 (3) °].

Related literature top

For related literature on scorpionate complexes, see: Bieller et al. (2006); Morawitz et al. (2008); Trofimenko (1993).

Experimental top

Mn(C₅H₃)(Bpz₃)₂(THF)₂ (64 mg, 75.4 µmol) was dissolved in THF (25 ml). The solution was irradiated using an UV lamp (TQ 150, λmax = 510 nm) for 16 h, whereupon the colourless solution turned orange. After stirring overnight at ambient temperature the reaction mixture was treated with 18-crown-6 (20 mg, 81.2 µmol) and was stirred for 10 minutes. After a small amount of colourless precipitate had been removed by filtration, the clear filtrate was evaporated to dryness in vacuo. Single crystals of (II) were grown from a solution of (II) in THF at -35°C.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering scheme. Displacement ellipsoids are at the 50% probability level. H atoms are drawn as small spheres of arbitrary radii.

(18-Crown-6)(pyrazolato-κ²N,N')potassium(I) top

Crystal data top

[K(C₃H₃N₂)(C₁₂H₂₄O₆)]	F(000) = 792
M_r = 370.49	D_x = 1.274 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 23906 reflections
a = 11.5330 (6) Å	θ = 2.5–25.9°
b = 8.2369 (5) Å	µ = 0.31 mm⁻¹
c = 20.7622 (10) Å	T = 173 K
β = 101.612 (4)°	Needle, colourless
V = 1931.96 (18) Å³	0.25 × 0.12 × 0.12 mm
Z = 4

Data collection top

STOE IPDS II two-circle- diffractometer	3602 independent reflections
Radiation source: fine-focus sealed tube	3234 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 25.6°, θ_min = 2.7°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −12→14
T_min = 0.919, T_max = 0.966	k = −9→9
23118 measured reflections	l = −25→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.036P)² + 0.3751P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3602 reflections	Δρ_max = 0.18 e Å⁻³
218 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0099 (8)

Crystal data top

[K(C₃H₃N₂)(C₁₂H₂₄O₆)]	V = 1931.96 (18) Å³
M_r = 370.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5330 (6) Å	µ = 0.31 mm⁻¹
b = 8.2369 (5) Å	T = 173 K
c = 20.7622 (10) Å	0.25 × 0.12 × 0.12 mm
β = 101.612 (4)°

Data collection top

STOE IPDS II two-circle- diffractometer	3602 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	3234 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.966	R_int = 0.034
23118 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
3602 reflections	Δρ_min = −0.20 e Å⁻³
218 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
K1	0.50031 (2)	0.36001 (3)	0.173982 (11)	0.02711 (9)
O1	0.70384 (7)	0.33603 (10)	0.10488 (4)	0.03149 (19)
C2	0.72895 (12)	0.16959 (15)	0.09518 (6)	0.0375 (3)
H2A	0.7929	0.1606	0.0699	0.045*
H2B	0.6576	0.1149	0.0700	0.045*
C3	0.76649 (11)	0.09050 (15)	0.16099 (6)	0.0341 (3)
H3A	0.7879	−0.0243	0.1554	0.041*
H3B	0.8366	0.1469	0.1866	0.041*
O4	0.67091 (7)	0.09896 (9)	0.19483 (4)	0.02900 (18)
C5	0.69922 (11)	0.02037 (14)	0.25736 (6)	0.0316 (3)
H5A	0.7675	0.0750	0.2856	0.038*
H5B	0.7209	−0.0943	0.2517	0.038*
C6	0.59374 (11)	0.02826 (13)	0.28891 (6)	0.0312 (3)
H6A	0.5233	−0.0153	0.2585	0.037*
H6B	0.6078	−0.0382	0.3295	0.037*
O7	0.57370 (7)	0.19353 (9)	0.30449 (4)	0.02792 (18)
C8	0.48115 (11)	0.20382 (16)	0.34087 (6)	0.0369 (3)
H8A	0.5059	0.1486	0.3838	0.044*
H8B	0.4093	0.1489	0.3164	0.044*
C9	0.45417 (11)	0.37812 (16)	0.35159 (6)	0.0358 (3)
H9A	0.3904	0.3860	0.3770	0.043*
H9B	0.5254	0.4330	0.3768	0.043*
O10	0.41787 (7)	0.45411 (10)	0.28931 (4)	0.0337 (2)
C11	0.38264 (12)	0.61956 (15)	0.29539 (6)	0.0373 (3)
H11A	0.4487	0.6822	0.3219	0.045*
H11B	0.3143	0.6243	0.3176	0.045*
C12	0.34937 (11)	0.68958 (16)	0.22762 (7)	0.0390 (3)
H12A	0.2892	0.6198	0.2000	0.047*
H12B	0.3147	0.7989	0.2298	0.047*
O13	0.45191 (7)	0.70035 (10)	0.19903 (4)	0.03146 (19)
C14	0.42386 (12)	0.77471 (15)	0.13533 (6)	0.0396 (3)
H14A	0.3977	0.8880	0.1394	0.047*
H14B	0.3586	0.7147	0.1069	0.047*
C15	0.53103 (13)	0.77270 (14)	0.10522 (6)	0.0397 (3)
H15A	0.5160	0.8371	0.0641	0.048*
H15B	0.5988	0.8219	0.1359	0.048*
O16	0.55811 (8)	0.60970 (9)	0.09139 (4)	0.03225 (19)
C17	0.65728 (12)	0.59892 (16)	0.05956 (6)	0.0390 (3)
H17A	0.7291	0.6427	0.0887	0.047*
H17B	0.6418	0.6632	0.0184	0.047*
C18	0.67551 (12)	0.42399 (17)	0.04447 (6)	0.0396 (3)
H18A	0.6026	0.3793	0.0167	0.047*
H18B	0.7408	0.4138	0.0202	0.047*
N21	0.32022 (9)	0.19783 (12)	0.09279 (5)	0.0333 (2)
N22	0.27171 (9)	0.34696 (12)	0.10107 (5)	0.0347 (2)
C23	0.16225 (12)	0.34869 (17)	0.06409 (6)	0.0405 (3)
H23	0.1094	0.4381	0.0609	0.049*
C24	0.13632 (13)	0.20214 (18)	0.03103 (6)	0.0444 (3)
H24	0.0654	0.1709	0.0019	0.053*
C25	0.23868 (13)	0.11318 (16)	0.05093 (6)	0.0387 (3)
H25	0.2499	0.0057	0.0368	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.02916 (14)	0.02496 (13)	0.02754 (13)	−0.00022 (9)	0.00652 (9)	0.00046 (9)
O1	0.0406 (5)	0.0316 (4)	0.0228 (4)	−0.0045 (4)	0.0075 (3)	−0.0025 (3)
C2	0.0438 (7)	0.0348 (6)	0.0376 (6)	−0.0046 (5)	0.0171 (5)	−0.0118 (5)
C3	0.0315 (6)	0.0282 (6)	0.0451 (7)	0.0019 (5)	0.0140 (5)	−0.0058 (5)
O4	0.0277 (4)	0.0273 (4)	0.0321 (4)	0.0044 (3)	0.0064 (3)	0.0016 (3)
C5	0.0347 (6)	0.0243 (5)	0.0333 (6)	0.0070 (5)	0.0008 (5)	0.0029 (4)
C6	0.0368 (6)	0.0217 (5)	0.0335 (6)	−0.0004 (5)	0.0030 (5)	0.0039 (4)
O7	0.0281 (4)	0.0248 (4)	0.0323 (4)	−0.0005 (3)	0.0096 (3)	0.0020 (3)
C8	0.0344 (6)	0.0399 (7)	0.0404 (7)	−0.0027 (5)	0.0172 (5)	0.0077 (5)
C9	0.0364 (7)	0.0442 (7)	0.0308 (6)	0.0010 (5)	0.0161 (5)	0.0006 (5)
O10	0.0379 (5)	0.0327 (4)	0.0324 (4)	0.0066 (3)	0.0114 (3)	−0.0026 (3)
C11	0.0365 (7)	0.0350 (6)	0.0440 (7)	0.0067 (5)	0.0166 (5)	−0.0078 (5)
C12	0.0308 (6)	0.0353 (6)	0.0506 (7)	0.0106 (5)	0.0076 (5)	−0.0033 (6)
O13	0.0326 (4)	0.0292 (4)	0.0309 (4)	0.0047 (3)	0.0022 (3)	0.0008 (3)
C14	0.0527 (8)	0.0266 (6)	0.0340 (6)	0.0080 (5)	−0.0041 (6)	0.0017 (5)
C15	0.0595 (8)	0.0254 (6)	0.0309 (6)	−0.0083 (6)	0.0010 (6)	0.0042 (5)
O16	0.0400 (5)	0.0275 (4)	0.0293 (4)	−0.0071 (3)	0.0070 (3)	0.0027 (3)
C17	0.0415 (7)	0.0466 (7)	0.0294 (6)	−0.0077 (6)	0.0086 (5)	0.0126 (5)
C18	0.0452 (7)	0.0526 (8)	0.0224 (5)	−0.0014 (6)	0.0104 (5)	0.0028 (5)
N21	0.0387 (6)	0.0322 (5)	0.0298 (5)	−0.0024 (4)	0.0092 (4)	0.0017 (4)
N22	0.0397 (6)	0.0325 (5)	0.0331 (5)	−0.0026 (4)	0.0099 (4)	0.0003 (4)
C23	0.0384 (7)	0.0470 (7)	0.0373 (7)	0.0047 (6)	0.0107 (5)	0.0084 (6)
C24	0.0434 (7)	0.0596 (9)	0.0271 (6)	−0.0151 (6)	−0.0002 (5)	0.0047 (6)
C25	0.0556 (8)	0.0352 (6)	0.0265 (6)	−0.0092 (6)	0.0107 (5)	−0.0017 (5)

Geometric parameters (Å, º) top

K1—N21	2.7441 (11)	C9—H9B	0.9900
K1—N22	2.7654 (11)	O10—C11	1.4349 (14)
K1—O16	2.8416 (8)	C11—C12	1.4976 (19)
K1—O10	2.8557 (8)	C11—H11A	0.9900
K1—O4	2.8877 (8)	C11—H11B	0.9900
K1—O13	2.9254 (8)	C12—O13	1.4286 (15)
K1—O1	2.9938 (9)	C12—H12A	0.9900
K1—O7	3.0025 (8)	C12—H12B	0.9900
K1—C12	3.5242 (12)	O13—C14	1.4341 (14)
O1—C2	1.4239 (15)	C14—C15	1.493 (2)
O1—C18	1.4282 (14)	C14—H14A	0.9900
C2—C3	1.4969 (18)	C14—H14B	0.9900
C2—H2A	0.9900	C15—O16	1.4207 (15)
C2—H2B	0.9900	C15—H15A	0.9900
C3—O4	1.4231 (14)	C15—H15B	0.9900
C3—H3A	0.9900	O16—C17	1.4343 (15)
C3—H3B	0.9900	C17—C18	1.498 (2)
O4—C5	1.4284 (13)	C17—H17A	0.9900
C5—C6	1.4946 (17)	C17—H17B	0.9900
C5—H5A	0.9900	C18—H18A	0.9900
C5—H5B	0.9900	C18—H18B	0.9900
C6—O7	1.4287 (13)	N21—C25	1.3405 (16)
C6—H6A	0.9900	N21—N22	1.3748 (15)
C6—H6B	0.9900	N22—C23	1.3391 (17)
O7—C8	1.4290 (14)	C23—C24	1.391 (2)
C8—C9	1.4951 (18)	C23—H23	0.9500
C8—H8A	0.9900	C24—C25	1.380 (2)
C8—H8B	0.9900	C24—H24	0.9500
C9—O10	1.4216 (14)	C25—H25	0.9500
C9—H9A	0.9900

N21—K1—N22	28.90 (3)	C9—C8—H8B	109.7
N21—K1—O16	102.83 (3)	H8A—C8—H8B	108.2
N22—K1—O16	90.65 (3)	O10—C9—C8	108.63 (10)
N21—K1—O10	107.98 (3)	O10—C9—H9A	110.0
N22—K1—O10	91.60 (3)	C8—C9—H9A	110.0
O16—K1—O10	117.88 (2)	O10—C9—H9B	110.0
N21—K1—O4	97.94 (3)	C8—C9—H9B	110.0
N22—K1—O4	126.79 (3)	H9A—C9—H9B	108.3
O16—K1—O4	113.20 (2)	C9—O10—C11	112.02 (9)
O10—K1—O4	114.09 (2)	C9—O10—K1	123.81 (6)
N21—K1—O13	115.33 (3)	C11—O10—K1	118.66 (7)
N22—K1—O13	86.54 (3)	O10—C11—C12	107.85 (10)
O16—K1—O13	59.34 (2)	O10—C11—H11A	110.1
O10—K1—O13	58.88 (2)	C12—C11—H11A	110.1
O4—K1—O13	146.67 (2)	O10—C11—H11B	110.1
N21—K1—O1	104.07 (3)	C12—C11—H11B	110.1
N22—K1—O1	119.22 (3)	H11A—C11—H11B	108.4
O16—K1—O1	57.10 (2)	O13—C12—C11	109.71 (10)
O10—K1—O1	147.69 (2)	O13—C12—K1	54.11 (5)
O4—K1—O1	56.39 (2)	C11—C12—K1	87.18 (7)
O13—K1—O1	110.15 (2)	O13—C12—H12A	109.7
N21—K1—O7	111.90 (3)	C11—C12—H12A	109.7
N22—K1—O7	122.74 (3)	K1—C12—H12A	72.7
O16—K1—O7	144.82 (2)	O13—C12—H12B	109.7
O10—K1—O7	56.51 (2)	C11—C12—H12B	109.7
O4—K1—O7	57.65 (2)	K1—C12—H12B	160.8
O13—K1—O7	107.84 (2)	H12A—C12—H12B	108.2
O1—K1—O7	107.25 (2)	C12—O13—C14	110.96 (9)
N21—K1—C12	102.02 (3)	C12—O13—K1	102.58 (7)
N22—K1—C12	74.09 (3)	C14—O13—K1	105.13 (6)
O16—K1—C12	79.86 (3)	O13—C14—C15	109.23 (10)
O10—K1—C12	42.01 (3)	O13—C14—H14A	109.8
O4—K1—C12	153.02 (3)	C15—C14—H14A	109.8
O13—K1—C12	23.31 (3)	O13—C14—H14B	109.8
O1—K1—C12	133.39 (3)	C15—C14—H14B	109.8
O7—K1—C12	97.71 (3)	H14A—C14—H14B	108.3
C2—O1—C18	112.41 (9)	O16—C15—C14	109.22 (10)
C2—O1—K1	109.43 (6)	O16—C15—H15A	109.8
C18—O1—K1	108.93 (7)	C14—C15—H15A	109.8
O1—C2—C3	108.64 (9)	O16—C15—H15B	109.8
O1—C2—H2A	110.0	C14—C15—H15B	109.8
C3—C2—H2A	110.0	H15A—C15—H15B	108.3
O1—C2—H2B	110.0	C15—O16—C17	112.31 (9)
C3—C2—H2B	110.0	C15—O16—K1	118.32 (7)
H2A—C2—H2B	108.3	C17—O16—K1	122.61 (7)
O4—C3—C2	108.59 (10)	O16—C17—C18	108.32 (10)
O4—C3—H3A	110.0	O16—C17—H17A	110.0
C2—C3—H3A	110.0	C18—C17—H17A	110.0
O4—C3—H3B	110.0	O16—C17—H17B	110.0
C2—C3—H3B	110.0	C18—C17—H17B	110.0
H3A—C3—H3B	108.4	H17A—C17—H17B	108.4
C3—O4—C5	111.62 (9)	O1—C18—C17	108.73 (10)
C3—O4—K1	122.31 (6)	O1—C18—H18A	109.9
C5—O4—K1	119.86 (6)	C17—C18—H18A	109.9
O4—C5—C6	108.74 (9)	O1—C18—H18B	109.9
O4—C5—H5A	109.9	C17—C18—H18B	109.9
C6—C5—H5A	109.9	H18A—C18—H18B	108.3
O4—C5—H5B	109.9	C25—N21—N22	107.20 (10)
C6—C5—H5B	109.9	C25—N21—K1	175.53 (9)
H5A—C5—H5B	108.3	N22—N21—K1	76.41 (6)
O7—C6—C5	108.89 (9)	C23—N22—N21	107.35 (10)
O7—C6—H6A	109.9	C23—N22—K1	176.68 (9)
C5—C6—H6A	109.9	N21—N22—K1	74.69 (6)
O7—C6—H6B	109.9	N22—C23—C24	110.97 (12)
C5—C6—H6B	109.9	N22—C23—H23	124.5
H6A—C6—H6B	108.3	C24—C23—H23	124.5
C6—O7—C8	110.38 (9)	C25—C24—C23	103.12 (11)
C6—O7—K1	105.07 (6)	C25—C24—H24	128.4
C8—O7—K1	110.19 (7)	C23—C24—H24	128.4
O7—C8—C9	109.61 (9)	N21—C25—C24	111.35 (12)
O7—C8—H8A	109.7	N21—C25—H25	124.3
C9—C8—H8A	109.7	C24—C25—H25	124.3
O7—C8—H8B	109.7

N21—K1—O1—C2	−57.90 (8)	O10—C11—C12—O13	−66.75 (13)
N22—K1—O1—C2	−84.52 (8)	O10—C11—C12—K1	−16.62 (9)
O16—K1—O1—C2	−154.25 (8)	N21—K1—C12—O13	−127.69 (7)
O10—K1—O1—C2	114.66 (8)	N22—K1—C12—O13	−120.20 (7)
O4—K1—O1—C2	32.36 (7)	O16—K1—C12—O13	−26.59 (6)
O13—K1—O1—C2	177.93 (7)	O10—K1—C12—O13	128.70 (8)
O7—K1—O1—C2	60.82 (7)	O4—K1—C12—O13	95.46 (8)
C12—K1—O1—C2	179.95 (7)	O1—K1—C12—O13	−4.80 (8)
N21—K1—O1—C18	65.36 (7)	O7—K1—C12—O13	117.87 (7)
N22—K1—O1—C18	38.75 (8)	N21—K1—C12—C11	115.40 (8)
O16—K1—O1—C18	−30.99 (7)	N22—K1—C12—C11	122.89 (8)
O10—K1—O1—C18	−122.08 (8)	O16—K1—C12—C11	−143.49 (8)
O4—K1—O1—C18	155.62 (8)	O10—K1—C12—C11	11.80 (7)
O13—K1—O1—C18	−58.81 (7)	O4—K1—C12—C11	−21.45 (11)
O7—K1—O1—C18	−175.92 (7)	O13—K1—C12—C11	−116.90 (11)
C12—K1—O1—C18	−56.79 (8)	O1—K1—C12—C11	−121.70 (7)
C18—O1—C2—C3	175.73 (10)	O7—K1—C12—C11	0.96 (8)
K1—O1—C2—C3	−63.09 (10)	C11—C12—O13—C14	−177.06 (10)
O1—C2—C3—O4	62.21 (12)	K1—C12—O13—C14	111.83 (9)
C2—C3—O4—C5	177.94 (9)	C11—C12—O13—K1	71.11 (10)
C2—C3—O4—K1	−29.89 (12)	N21—K1—O13—C12	58.90 (7)
N21—K1—O4—C3	101.35 (8)	N22—K1—O13—C12	56.37 (7)
N22—K1—O4—C3	103.29 (8)	O16—K1—O13—C12	149.19 (7)
O16—K1—O4—C3	−6.34 (8)	O10—K1—O13—C12	−37.60 (7)
O10—K1—O4—C3	−144.84 (8)	O4—K1—O13—C12	−124.72 (7)
O13—K1—O4—C3	−75.35 (9)	O1—K1—O13—C12	176.29 (7)
O1—K1—O4—C3	−0.30 (7)	O7—K1—O13—C12	−66.97 (7)
O7—K1—O4—C3	−147.70 (8)	N21—K1—O13—C14	−57.21 (8)
C12—K1—O4—C3	−121.14 (9)	N22—K1—O13—C14	−59.73 (7)
N21—K1—O4—C5	−108.68 (8)	O16—K1—O13—C14	33.09 (7)
N22—K1—O4—C5	−106.74 (8)	O10—K1—O13—C14	−153.70 (8)
O16—K1—O4—C5	143.63 (7)	O4—K1—O13—C14	119.17 (8)
O10—K1—O4—C5	5.13 (8)	O1—K1—O13—C14	60.18 (8)
O13—K1—O4—C5	74.62 (9)	O7—K1—O13—C14	176.92 (7)
O1—K1—O4—C5	149.67 (8)	C12—K1—O13—C14	−116.10 (10)
O7—K1—O4—C5	2.26 (7)	C12—O13—C14—C15	−175.93 (9)
C12—K1—O4—C5	28.83 (11)	K1—O13—C14—C15	−65.73 (10)
C3—O4—C5—C6	−177.84 (9)	O13—C14—C15—O16	67.33 (12)
K1—O4—C5—C6	29.22 (11)	C14—C15—O16—C17	177.37 (9)
O4—C5—C6—O7	−67.15 (11)	C14—C15—O16—K1	−30.65 (12)
C5—C6—O7—C8	−173.98 (9)	N21—K1—O16—C15	111.08 (8)
C5—C6—O7—K1	67.25 (9)	N22—K1—O16—C15	84.64 (8)
N21—K1—O7—C6	51.07 (7)	O10—K1—O16—C15	−7.51 (9)
N22—K1—O7—C6	81.39 (7)	O4—K1—O16—C15	−144.33 (8)
O16—K1—O7—C6	−119.30 (7)	O13—K1—O16—C15	−0.94 (8)
O10—K1—O7—C6	148.71 (7)	O1—K1—O16—C15	−150.32 (9)
O4—K1—O7—C6	−34.43 (6)	O7—K1—O16—C15	−78.07 (9)
O13—K1—O7—C6	178.94 (6)	C12—K1—O16—C15	10.94 (8)
O1—K1—O7—C6	−62.45 (7)	N21—K1—O16—C17	−99.97 (8)
C12—K1—O7—C6	157.38 (6)	N22—K1—O16—C17	−126.41 (8)
N21—K1—O7—C8	−67.83 (7)	O10—K1—O16—C17	141.43 (8)
N22—K1—O7—C8	−37.51 (8)	O4—K1—O16—C17	4.61 (9)
O16—K1—O7—C8	121.80 (7)	O13—K1—O16—C17	148.00 (9)
O10—K1—O7—C8	29.81 (7)	O1—K1—O16—C17	−1.38 (8)
O4—K1—O7—C8	−153.33 (8)	O7—K1—O16—C17	70.88 (9)
O13—K1—O7—C8	60.04 (7)	C12—K1—O16—C17	159.88 (8)
O1—K1—O7—C8	178.65 (7)	C15—O16—C17—C18	−177.58 (10)
C12—K1—O7—C8	38.48 (7)	K1—O16—C17—C18	31.82 (12)
C6—O7—C8—C9	−175.05 (10)	C2—O1—C18—C17	−176.81 (10)
K1—O7—C8—C9	−59.45 (11)	K1—O1—C18—C17	61.72 (11)
O7—C8—C9—O10	59.92 (13)	O16—C17—C18—O1	−62.76 (13)
C8—C9—O10—C11	176.08 (10)	O16—K1—N21—N22	−67.14 (6)
C8—C9—O10—K1	−30.63 (13)	O10—K1—N21—N22	58.19 (6)
N21—K1—O10—C9	106.21 (9)	O4—K1—N21—N22	176.78 (6)
N22—K1—O10—C9	130.46 (9)	O13—K1—N21—N22	−5.23 (7)
O16—K1—O10—C9	−137.95 (8)	O1—K1—N21—N22	−125.99 (6)
O4—K1—O10—C9	−1.51 (9)	O7—K1—N21—N22	118.53 (6)
O13—K1—O10—C9	−144.56 (9)	C12—K1—N21—N22	15.04 (6)
O1—K1—O10—C9	−66.20 (10)	C25—N21—N22—C23	0.02 (12)
O7—K1—O10—C9	1.40 (8)	K1—N21—N22—C23	177.28 (9)
C12—K1—O10—C9	−165.70 (10)	C25—N21—N22—K1	−177.26 (9)
N21—K1—O10—C11	−102.15 (8)	O16—K1—N22—N21	116.04 (6)
N22—K1—O10—C11	−77.90 (8)	O10—K1—N22—N21	−126.04 (6)
O16—K1—O10—C11	13.69 (9)	O4—K1—N22—N21	−3.98 (7)
O4—K1—O10—C11	150.13 (8)	O13—K1—N22—N21	175.27 (6)
O13—K1—O10—C11	7.09 (8)	O1—K1—N22—N21	64.07 (6)
O1—K1—O10—C11	85.44 (9)	O7—K1—N22—N21	−75.70 (6)
O7—K1—O10—C11	153.04 (9)	C12—K1—N22—N21	−164.70 (6)
C12—K1—O10—C11	−14.06 (8)	N21—N22—C23—C24	0.11 (14)
C9—O10—C11—C12	178.50 (10)	N22—C23—C24—C25	−0.18 (14)
K1—O10—C11—C12	23.70 (12)	C23—C24—C25—N21	0.19 (14)

Experimental details

Crystal data
Chemical formula	[K(C₃H₃N₂)(C₁₂H₂₄O₆)]
M_r	370.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	11.5330 (6), 8.2369 (5), 20.7622 (10)
β (°)	101.612 (4)
V (Å³)	1931.96 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.25 × 0.12 × 0.12

Data collection
Diffractometer	STOE IPDS II two-circle- diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.919, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	23118, 3602, 3234
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.066, 1.03
No. of reflections	3602
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

References

Bieller, S., Haghiri, A., Bolte, M., Bats, J. W., Wagner, M. & Lerner, H.-W. (2006). Inorg. Chim. Acta, 359, 1559–1572. Web of Science CSD CrossRef CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Morawitz, M., Zhang, F., Bolte, M., Bats, J. W., Lerner, H.-W. & Wagner, M. (2008). Organometallics, 27, 5067–5074. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Trofimenko, S. (1993). Chem. Rev. 93, 943–980. CrossRef CAS Web of Science Google Scholar