Poly[μ2-aqua-μ4-[1-(4-chloro­phen­yl)-4,4,4-tri­fluoro­butane-1,3-dionato]-potassium]

Martins, J.P.; Arranja, C.C.; Sobral, A.J.F.N.; Ramos Silva, M.

doi:10.1107/S1600536813017388

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages m422-m423

https://doi.org/10.1107/S1600536813017388

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Poly[μ₂-aqua-μ₄-[1-(4-chlorophenyl)-4,4,4-trifluorobutane-1,3-dionato]-potassium]

João P. Martins,^a Cláudia C. Arranja,^b Abílio J. F. N. Sobral ^b and Manuela Ramos Silva ^a ^*

^aCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^bChemistry Department, University of Coimbra, P-3004 Coimbra, Portugal
^*Correspondence e-mail: manuela@pollux.fis.uc.pt

(Received 13 June 2013; accepted 24 June 2013; online 29 June 2013)

In the title compound, [K(C₁₀H₅ClO₂F₃)(H₂O)]_n, the two independent K⁺ ions are located on a twofold rotation axis. For each of the cations, the distorted cubic coordination environment is defined by two F and four O atoms of symmetry-related 1,4-chlorophenyl-4,4,4-trifluorobutane-1,3-dionate anions and by two O atoms of water molecules. The μ₄-bridging character of the anion and the μ₂-bridging of the water molecule lead to the formation of layers parallel to (100). The coordinating water molecules are also involved in O—H⋯O hydrogen bonds that reinforce the molecular cohesion within the layers, which are stacked along [100]. The β-diketonate anion is not planar, with an angle of 31.78 (10)° between the mean planes of the diketonate group and the chlorophenyl ring.

Related literature

For background to lanthanide complexes with diketonate ligands, see: Martín-Ramos et al. (2013a ,b ).

Experimental

Crystal data

[K(C₁₀H₅ClF₃O₂)(H₂O)]
M_r = 306.71
Monoclinic, C 2/c
a = 30.164 (2) Å
b = 8.0739 (4) Å
c = 10.2696 (5) Å
β = 98.752 (2)°
V = 2471.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 293 K
0.20 × 0.11 × 0.08 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.830, T_max = 0.999
11396 measured reflections
2182 independent reflections
1559 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.01
2182 reflections
170 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1W⋯O2	0.82 (3)	1.90 (3)	2.709 (2)	173 (3)
O3—H2W⋯O1ⁱ	0.87 (3)	2.06 (3)	2.843 (3)	150 (2)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813017388/wm2752sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017388/wm2752Isup2.hkl

checkCIF report

Comment top

The title compound, [K(C₁₀H₅ClO₂F₃)(H₂O)], Fig. 1, was obtained serendipitously as part of a project to synthesize new lanthanide coordination complexes as potential emissive layers in organic light emitting diodes (OLEDs) (Martín-Ramos, 2013a,b).

The title compound contains two potassium ions, one 1,4-chlorophenyl-4,4,4-trifluoro-1,3-butanedionate anion and one coordinating water molecule in the asymmetric unit. Both potassium ions are situated on twofold rotation axes and are in the centres of distorted cubes, that are formed by two F and six O atoms. The cations are arranged in alternating chains along [010], Fig. 2, with K···K distances of 3.6379 (11) and 4.4360 (11) Å, respectively. The cations are bridged by two water molecules and one bis-monodentate CF₃ group, as well as by four oxygen atoms of two β-diketonate groups. The chains are joined into layers parallel to (100) since each diketonate coordinates potassium ions from two adjacent chains. The β-diketonate ligand is not planar with an angle of 31.78 (10)° between the mean planes of the diketonate group and the chlorophenyl ring. Within the layers, there are hydrogen bonds between the coordinating water molecules and adjacent diketonate O atoms (Table 1, Fig. 3). The unit cell does not contain any residual solvent acessible voids.

Related literature top

For background to lanthanide complexes with diketonate ligands, see: Martín-Ramos et al. (2013a,b).

Experimental top

Firstly, 0.5 mmol of europium(III) nitrate pentahydrate were dissolved in 20 ml of methanol followed by the addition of 0.9 ml of potassium methoxide. This solution was left to reflux at 353 K for 15 min. Secondly, 1.5 mmol of 1,14 chlorophenyl-4,4,4-trifluoro-1,3-butanedionate were dissolved in 15 ml of methanol and added to the main solution. After decanting the resulting solution, 0.5 mmol of bathophenanthroline were dissolved in 10 ml of methanol and added to the main solution. The main solution was then transferred from a volumetric balloon to a beaker covered with paraffin film and placed on a water bath at 303 K until complete evaporation was verified. Since from the evaporation process no crystals were obtained, all the material from this batch was dissolved in 25 ml of chloroform. A light orange powder was formed alongside with some transparent crystals. The powder was studied by X-ray powder diffraction and was proven to be amorphous; the transparent crystals were studied by single-crystal X-ray diffraction, and as a result, the title compound was revealed.

Structure description top

For background to lanthanide complexes with diketonate ligands, see: Martín-Ramos et al. (2013a,b).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEPII plot of the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of the components in the title structure. For clarity, the Cl and H atoms were omitted. Atoms C5 to C10 defining the benzene ring were also omitted.
	Fig. 3. Packing of the components showing the hydrogen bonding interactions as dashed lines.

Poly[µ₂-aqua-µ₄-[1-(4-chlorophenyl)-4,4,4-trifluorobutane-1,3-dionato]-potassium] top

Crystal data top

[K(C₁₀H₅ClF₃O₂)(H₂O)]	F(000) = 1232
M_r = 306.71	D_x = 1.648 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3474 reflections
a = 30.164 (2) Å	θ = 2.7–23.9°
b = 8.0739 (4) Å	µ = 0.68 mm⁻¹
c = 10.2696 (5) Å	T = 293 K
β = 98.752 (2)°	Prism, colourless
V = 2471.9 (2) Å³	0.20 × 0.11 × 0.08 mm
Z = 8

Data collection top

Bruker APEX CCD area-detector diffractometer	2182 independent reflections
Radiation source: fine-focus sealed tube	1559 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 25.8°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −35→36
T_min = 0.830, T_max = 0.999	k = −9→9
11396 measured reflections	l = −12→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0532P)² + 0.5088P] where P = (F_o² + 2F_c²)/3
2182 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

[K(C₁₀H₅ClF₃O₂)(H₂O)]	V = 2471.9 (2) Å³
M_r = 306.71	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.164 (2) Å	µ = 0.68 mm⁻¹
b = 8.0739 (4) Å	T = 293 K
c = 10.2696 (5) Å	0.20 × 0.11 × 0.08 mm
β = 98.752 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	2182 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	1559 reflections with I > 2σ(I)
T_min = 0.830, T_max = 0.999	R_int = 0.032
11396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.19 e Å⁻³
2182 reflections	Δρ_min = −0.20 e Å⁻³
170 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	0.0000	−0.01267 (9)	0.7500	0.0468 (2)
K2	0.0000	0.53676 (9)	0.7500	0.0505 (2)
Cl1	−0.25418 (2)	0.31387 (12)	−0.31250 (7)	0.0774 (3)
F1	−0.08518 (5)	0.13336 (19)	0.59626 (14)	0.0684 (5)
F2	−0.14447 (5)	0.2619 (2)	0.51303 (15)	0.0765 (5)
F3	−0.08456 (5)	0.3946 (2)	0.58351 (15)	0.0742 (5)
O1	−0.06701 (5)	0.22988 (19)	0.11627 (16)	0.0462 (4)
O2	−0.04203 (5)	0.2360 (2)	0.39484 (16)	0.0536 (5)
O3	0.02269 (7)	0.2670 (2)	0.60726 (18)	0.0554 (5)
H1W	0.0018 (10)	0.254 (3)	0.548 (3)	0.067*
H2W	0.0446 (10)	0.267 (3)	0.561 (3)	0.067*
C1	−0.10053 (8)	0.2594 (3)	0.5178 (2)	0.0463 (6)
C2	−0.08424 (7)	0.2490 (3)	0.3853 (2)	0.0390 (6)
C3	−0.11551 (7)	0.2554 (3)	0.2741 (2)	0.0433 (6)
H3	−0.1455	0.2651	0.2848	0.052*
C4	−0.10548 (7)	0.2484 (3)	0.1436 (2)	0.0388 (6)
C5	−0.14351 (7)	0.2644 (3)	0.0318 (2)	0.0387 (6)
C6	−0.18115 (7)	0.3592 (3)	0.0416 (2)	0.0479 (6)
H6	−0.1838	0.4116	0.1207	0.058*
C7	−0.21485 (7)	0.3765 (3)	−0.0651 (2)	0.0532 (7)
H7	−0.2397	0.4428	−0.0589	0.064*
C8	−0.21129 (8)	0.2955 (3)	−0.1788 (2)	0.0504 (7)
C9	−0.17475 (8)	0.1981 (3)	−0.1915 (2)	0.0552 (7)
H9	−0.1730	0.1419	−0.2696	0.066*
C10	−0.14087 (7)	0.1860 (3)	−0.0857 (2)	0.0481 (6)
H10	−0.1156	0.1232	−0.0938	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0449 (4)	0.0434 (5)	0.0523 (5)	0.000	0.0085 (3)	0.000
K2	0.0554 (5)	0.0446 (5)	0.0519 (5)	0.000	0.0097 (4)	0.000
Cl1	0.0570 (4)	0.1091 (7)	0.0574 (5)	−0.0104 (4)	−0.0191 (3)	0.0140 (4)
F1	0.0833 (10)	0.0700 (11)	0.0512 (9)	0.0116 (8)	0.0084 (8)	0.0191 (8)
F2	0.0436 (9)	0.1365 (16)	0.0512 (10)	0.0094 (8)	0.0132 (7)	0.0033 (9)
F3	0.0891 (11)	0.0680 (11)	0.0655 (10)	0.0008 (8)	0.0123 (8)	−0.0252 (9)
O1	0.0340 (9)	0.0642 (12)	0.0406 (9)	0.0020 (7)	0.0066 (7)	0.0005 (8)
O2	0.0340 (9)	0.0819 (13)	0.0434 (10)	0.0043 (7)	0.0013 (7)	−0.0037 (9)
O3	0.0436 (10)	0.0839 (14)	0.0388 (11)	0.0022 (9)	0.0063 (8)	−0.0031 (9)
C1	0.0429 (14)	0.0520 (16)	0.0430 (15)	0.0037 (11)	0.0034 (11)	−0.0001 (13)
C2	0.0368 (12)	0.0393 (14)	0.0408 (14)	0.0012 (9)	0.0055 (10)	−0.0001 (10)
C3	0.0309 (12)	0.0586 (16)	0.0402 (15)	0.0010 (10)	0.0050 (10)	0.0022 (12)
C4	0.0332 (12)	0.0410 (14)	0.0416 (15)	−0.0022 (9)	0.0035 (10)	0.0018 (11)
C5	0.0335 (12)	0.0437 (14)	0.0385 (14)	−0.0046 (9)	0.0047 (10)	0.0012 (11)
C6	0.0411 (13)	0.0571 (17)	0.0441 (15)	0.0034 (11)	0.0017 (11)	−0.0026 (12)
C7	0.0395 (13)	0.0629 (18)	0.0543 (17)	0.0059 (11)	−0.0018 (12)	0.0059 (14)
C8	0.0386 (14)	0.0657 (18)	0.0429 (16)	−0.0107 (12)	−0.0064 (11)	0.0128 (14)
C9	0.0522 (15)	0.0742 (19)	0.0384 (15)	−0.0107 (13)	0.0044 (12)	−0.0042 (13)
C10	0.0396 (13)	0.0591 (16)	0.0457 (16)	−0.0009 (11)	0.0064 (11)	−0.0006 (13)

Geometric parameters (Å, º) top

K1—O2ⁱ	2.7648 (17)	O1—C4	1.244 (3)
K1—O2ⁱⁱ	2.7648 (17)	O2—C2	1.266 (3)
K1—O3ⁱⁱⁱ	2.832 (2)	O3—H1W	0.82 (3)
K1—O3	2.832 (2)	O3—H2W	0.87 (3)
K1—O1ⁱ	2.8640 (15)	C1—C2	1.518 (4)
K1—O1ⁱⁱ	2.8641 (15)	C2—C3	1.367 (3)
K1—F1ⁱⁱⁱ	3.0415 (15)	C3—C4	1.419 (3)
K1—F1	3.0415 (15)	C3—H3	0.9300
K2—O3	2.7686 (19)	C4—C5	1.500 (3)
K2—O3ⁱⁱⁱ	2.7686 (19)	C5—C10	1.376 (3)
K2—O2^iv	2.7859 (17)	C5—C6	1.385 (3)
K2—O2^v	2.7860 (17)	C6—C7	1.384 (3)
K2—O1^iv	2.9457 (16)	C6—H6	0.9300
K2—O1^v	2.9457 (16)	C7—C8	1.357 (3)
K2—F3ⁱⁱⁱ	3.0692 (16)	C7—H7	0.9300
K2—F3	3.0692 (16)	C8—C9	1.376 (4)
Cl1—C8	1.744 (2)	C9—C10	1.378 (3)
F1—C1	1.336 (3)	C9—H9	0.9300
F2—C1	1.319 (3)	C10—H10	0.9300
F3—C1	1.334 (3)

O2ⁱ—K1—O2ⁱⁱ	98.61 (7)	O2^iv—K2—F3	110.86 (4)
O2ⁱ—K1—O3ⁱⁱⁱ	164.81 (6)	O2^v—K2—F3	97.85 (4)
O2ⁱⁱ—K1—O3ⁱⁱⁱ	94.28 (5)	O1^iv—K2—F3	162.20 (5)
O2ⁱ—K1—O3	94.29 (5)	O1^v—K2—F3	61.73 (4)
O2ⁱⁱ—K1—O3	164.80 (5)	F3ⁱⁱⁱ—K2—F3	136.07 (7)
O3ⁱⁱⁱ—K1—O3	74.25 (8)	C1—F3—K2	142.49 (14)
O2ⁱ—K1—O1ⁱ	60.71 (5)	C4—O1—K1ⁱ	125.44 (14)
O2ⁱⁱ—K1—O1ⁱ	71.98 (5)	C4—O1—K2^iv	114.54 (13)
O3ⁱⁱⁱ—K1—O1ⁱ	116.65 (5)	K1ⁱ—O1—K2^iv	77.52 (4)
O3—K1—O1ⁱ	121.86 (5)	C2—O2—K1ⁱ	123.39 (13)
O2ⁱ—K1—O1ⁱⁱ	71.98 (5)	C2—O2—K2^iv	115.97 (13)
O2ⁱⁱ—K1—O1ⁱⁱ	60.71 (5)	K1ⁱ—O2—K2^iv	81.90 (5)
O3ⁱⁱⁱ—K1—O1ⁱⁱ	121.86 (5)	K2—O3—K1	104.74 (6)
O3—K1—O1ⁱⁱ	116.65 (5)	H1W—O3—H2W	99 (3)
O1ⁱ—K1—O1ⁱⁱ	104.48 (7)	F2—C1—F3	106.9 (2)
O2ⁱ—K1—F1ⁱⁱⁱ	96.41 (4)	F2—C1—F1	106.7 (2)
O2ⁱⁱ—K1—F1ⁱⁱⁱ	113.20 (4)	F3—C1—F1	104.6 (2)
O3ⁱⁱⁱ—K1—F1ⁱⁱⁱ	70.97 (5)	F2—C1—C2	115.3 (2)
O3—K1—F1ⁱⁱⁱ	73.02 (5)	F3—C1—C2	111.0 (2)
O1ⁱ—K1—F1ⁱⁱⁱ	60.63 (4)	F1—C1—C2	111.62 (19)
O1ⁱⁱ—K1—F1ⁱⁱⁱ	164.83 (5)	O2—C2—C3	128.8 (2)
O2ⁱ—K1—F1	113.19 (4)	O2—C2—C1	113.20 (19)
O2ⁱⁱ—K1—F1	96.41 (4)	C3—C2—C1	118.0 (2)
O3ⁱⁱⁱ—K1—F1	73.02 (5)	O2—C2—K2^iv	45.21 (11)
O3—K1—F1	70.97 (5)	C3—C2—K2^iv	95.70 (15)
O1ⁱ—K1—F1	164.83 (5)	C1—C2—K2^iv	132.56 (14)
O1ⁱⁱ—K1—F1	60.63 (4)	C2—C3—C4	124.6 (2)
F1ⁱⁱⁱ—K1—F1	134.38 (6)	C2—C3—H3	117.7
O3—K2—O3ⁱⁱⁱ	76.27 (8)	C4—C3—H3	117.7
O3—K2—O2^iv	93.79 (5)	O1—C4—C3	124.0 (2)
O3ⁱⁱⁱ—K2—O2^iv	165.95 (6)	O1—C4—C5	117.9 (2)
O3—K2—O2^v	165.95 (6)	C3—C4—C5	118.12 (19)
O3ⁱⁱⁱ—K2—O2^v	93.79 (5)	C10—C5—C6	118.4 (2)
O2^iv—K2—O2^v	97.60 (7)	C10—C5—C4	119.5 (2)
O3—K2—O1^iv	122.86 (5)	C6—C5—C4	122.1 (2)
O3ⁱⁱⁱ—K2—O1^iv	117.62 (5)	C7—C6—C5	120.7 (2)
O2^iv—K2—O1^iv	59.46 (5)	C7—C6—H6	119.7
O2^v—K2—O1^iv	70.46 (5)	C5—C6—H6	119.7
O3—K2—O1^v	117.62 (5)	C8—C7—C6	119.2 (2)
O3ⁱⁱⁱ—K2—O1^v	122.86 (5)	C8—C7—H7	120.4
O2^iv—K2—O1^v	70.46 (5)	C6—C7—H7	120.4
O2^v—K2—O1^v	59.46 (5)	C7—C8—C9	121.8 (2)
O1^iv—K2—O1^v	100.47 (6)	C7—C8—Cl1	119.4 (2)
O3—K2—F3ⁱⁱⁱ	75.48 (5)	C9—C8—Cl1	118.9 (2)
O3ⁱⁱⁱ—K2—F3ⁱⁱⁱ	70.27 (5)	C8—C9—C10	118.3 (2)
O2^iv—K2—F3ⁱⁱⁱ	97.85 (4)	C8—C9—H9	120.8
O2^v—K2—F3ⁱⁱⁱ	110.86 (5)	C10—C9—H9	120.8
O1^iv—K2—F3ⁱⁱⁱ	61.73 (4)	C5—C10—C9	121.6 (2)
O1^v—K2—F3ⁱⁱⁱ	162.20 (5)	C5—C10—H10	119.2
O3—K2—F3	70.26 (5)	C9—C10—H10	119.2
O3ⁱⁱⁱ—K2—F3	75.48 (5)

O2ⁱ—K1—K2—O3	13.40 (8)	O3ⁱⁱⁱ—K1—F1—C1	74.8 (2)
O2ⁱⁱ—K1—K2—O3	−166.60 (8)	O3—K1—F1—C1	−3.9 (2)
O3ⁱⁱⁱ—K1—K2—O3	180.0	O1ⁱ—K1—F1—C1	−153.4 (2)
O1ⁱ—K1—K2—O3	94.77 (8)	O1ⁱⁱ—K1—F1—C1	−141.6 (2)
O1ⁱⁱ—K1—K2—O3	−85.23 (8)	F1ⁱⁱⁱ—K1—F1—C1	35.7 (2)
F1ⁱⁱⁱ—K1—K2—O3	91.76 (7)	K2^vi—K1—F1—C1	−144.3 (2)
F1—K1—K2—O3	−88.24 (7)	K2—K1—F1—C1	35.7 (2)
O2ⁱ—K1—K2—O3ⁱⁱⁱ	−166.60 (8)	O3—K2—F3—C1	18.3 (2)
O2ⁱⁱ—K1—K2—O3ⁱⁱⁱ	13.40 (8)	O3ⁱⁱⁱ—K2—F3—C1	−62.1 (2)
O3—K1—K2—O3ⁱⁱⁱ	179.998 (1)	O2^iv—K2—F3—C1	104.8 (2)
O1ⁱ—K1—K2—O3ⁱⁱⁱ	−85.23 (8)	O2^v—K2—F3—C1	−154.0 (2)
O1ⁱⁱ—K1—K2—O3ⁱⁱⁱ	94.77 (8)	O1^iv—K2—F3—C1	158.5 (2)
F1ⁱⁱⁱ—K1—K2—O3ⁱⁱⁱ	−88.25 (7)	O1^v—K2—F3—C1	157.1 (3)
F1—K1—K2—O3ⁱⁱⁱ	91.75 (7)	F3ⁱⁱⁱ—K2—F3—C1	−22.6 (2)
O2ⁱ—K1—K2—O2^iv	0.0	C2^iv—K2—F3—C1	89.0 (2)
O2ⁱⁱ—K1—K2—O2^iv	180.0	C2^v—K2—F3—C1	−150.4 (2)
O3ⁱⁱⁱ—K1—K2—O2^iv	166.60 (8)	K1^vii—K2—F3—C1	157.4 (2)
O3—K1—K2—O2^iv	−13.40 (8)	K1—K2—F3—C1	−22.6 (2)
O1ⁱ—K1—K2—O2^iv	81.37 (6)	O3ⁱⁱⁱ—K2—O3—K1	0.0
O1ⁱⁱ—K1—K2—O2^iv	−98.63 (6)	O2^iv—K2—O3—K1	169.93 (6)
F1ⁱⁱⁱ—K1—K2—O2^iv	78.35 (5)	O2^v—K2—O3—K1	−45.9 (2)
F1—K1—K2—O2^iv	−101.65 (5)	O1^iv—K2—O3—K1	114.23 (6)
O2ⁱ—K1—K2—O2^v	180.0	O1^v—K2—O3—K1	−120.17 (5)
O2ⁱⁱ—K1—K2—O2^v	0.0	F3ⁱⁱⁱ—K2—O3—K1	72.79 (6)
O3ⁱⁱⁱ—K1—K2—O2^v	−13.40 (8)	F3—K2—O3—K1	−79.25 (6)
O3—K1—K2—O2^v	166.60 (8)	C2^iv—K2—O3—K1	152.89 (7)
O1ⁱ—K1—K2—O2^v	−98.63 (6)	C2^v—K2—O3—K1	−58.15 (12)
O1ⁱⁱ—K1—K2—O2^v	81.36 (6)	K1^vii—K2—O3—K1	180.0
F1ⁱⁱⁱ—K1—K2—O2^v	−101.65 (5)	O2ⁱ—K1—O3—K2	−169.85 (6)
F1—K1—K2—O2^v	78.35 (5)	O2ⁱⁱ—K1—O3—K2	42.1 (2)
O2ⁱ—K1—K2—O1^iv	−81.37 (6)	O3ⁱⁱⁱ—K1—O3—K2	0.0
O2ⁱⁱ—K1—K2—O1^iv	98.63 (6)	O1ⁱ—K1—O3—K2	−111.93 (6)
O3ⁱⁱⁱ—K1—K2—O1^iv	85.23 (8)	O1ⁱⁱ—K1—O3—K2	118.17 (6)
O3—K1—K2—O1^iv	−94.77 (8)	F1ⁱⁱⁱ—K1—O3—K2	−74.44 (6)
O1ⁱ—K1—K2—O1^iv	0.0	F1—K1—O3—K2	77.08 (6)
O1ⁱⁱ—K1—K2—O1^iv	179.999 (1)	K2^vi—K1—O3—K2	180.0
F1ⁱⁱⁱ—K1—K2—O1^iv	−3.01 (5)	K2—F3—C1—F2	155.52 (15)
F1—K1—K2—O1^iv	176.99 (5)	K2—F3—C1—F1	42.6 (3)
O2ⁱ—K1—K2—O1^v	98.63 (6)	K2—F3—C1—C2	−78.0 (3)
O2ⁱⁱ—K1—K2—O1^v	−81.36 (6)	K1—F1—C1—F2	−165.34 (14)
O3ⁱⁱⁱ—K1—K2—O1^v	−94.77 (8)	K1—F1—C1—F3	−52.3 (3)
O3—K1—K2—O1^v	85.23 (8)	K1—F1—C1—C2	67.8 (3)
O1ⁱ—K1—K2—O1^v	180.0	K1ⁱ—O2—C2—C3	−45.8 (3)
O1ⁱⁱ—K1—K2—O1^v	0.0	K2^iv—O2—C2—C3	51.9 (3)
F1ⁱⁱⁱ—K1—K2—O1^v	176.99 (5)	K1ⁱ—O2—C2—C1	134.65 (16)
F1—K1—K2—O1^v	−3.01 (5)	K2^iv—O2—C2—C1	−127.69 (16)
O2ⁱ—K1—K2—F3ⁱⁱⁱ	−80.95 (5)	K1ⁱ—O2—C2—K2^iv	−97.66 (15)
O2ⁱⁱ—K1—K2—F3ⁱⁱⁱ	99.05 (5)	F2—C1—C2—O2	−175.63 (19)
O3ⁱⁱⁱ—K1—K2—F3ⁱⁱⁱ	85.65 (7)	F3—C1—C2—O2	62.7 (3)
O3—K1—K2—F3ⁱⁱⁱ	−94.36 (7)	F1—C1—C2—O2	−53.6 (3)
O1ⁱ—K1—K2—F3ⁱⁱⁱ	0.41 (5)	F2—C1—C2—C3	4.7 (3)
O1ⁱⁱ—K1—K2—F3ⁱⁱⁱ	−179.59 (5)	F3—C1—C2—C3	−116.9 (2)
F1ⁱⁱⁱ—K1—K2—F3ⁱⁱⁱ	−2.60 (4)	F1—C1—C2—C3	126.8 (2)
F1—K1—K2—F3ⁱⁱⁱ	177.40 (4)	F2—C1—C2—K2^iv	134.69 (17)
O2ⁱ—K1—K2—F3	99.05 (5)	F3—C1—C2—K2^iv	13.0 (3)
O2ⁱⁱ—K1—K2—F3	−80.95 (5)	F1—C1—C2—K2^iv	−103.3 (2)
O3ⁱⁱⁱ—K1—K2—F3	−94.35 (7)	O2—C2—C3—C4	−0.1 (4)
O3—K1—K2—F3	85.64 (7)	C1—C2—C3—C4	179.5 (2)
O1ⁱ—K1—K2—F3	−179.59 (5)	K2^iv—C2—C3—C4	34.1 (2)
O1ⁱⁱ—K1—K2—F3	0.41 (5)	K1ⁱ—O1—C4—C3	40.2 (3)
F1ⁱⁱⁱ—K1—K2—F3	177.40 (4)	K2^iv—O1—C4—C3	−51.7 (2)
F1—K1—K2—F3	−2.60 (4)	K1ⁱ—O1—C4—C5	−139.83 (15)
O2ⁱ—K1—K2—C2^iv	−18.02 (6)	K2^iv—O1—C4—C5	128.26 (16)
O2ⁱⁱ—K1—K2—C2^iv	161.98 (6)	C2—C3—C4—O1	2.5 (4)
O3ⁱⁱⁱ—K1—K2—C2^iv	148.58 (8)	C2—C3—C4—C5	−177.4 (2)
O3—K1—K2—C2^iv	−31.42 (8)	O1—C4—C5—C10	30.2 (3)
O1ⁱ—K1—K2—C2^iv	63.35 (6)	C3—C4—C5—C10	−149.8 (2)
O1ⁱⁱ—K1—K2—C2^iv	−116.65 (6)	O1—C4—C5—C6	−148.3 (2)
F1ⁱⁱⁱ—K1—K2—C2^iv	60.33 (5)	C3—C4—C5—C6	31.6 (3)
F1—K1—K2—C2^iv	−119.67 (5)	C10—C5—C6—C7	−1.1 (3)
O2ⁱ—K1—K2—C2^v	161.98 (6)	C4—C5—C6—C7	177.5 (2)
O2ⁱⁱ—K1—K2—C2^v	−18.02 (6)	C5—C6—C7—C8	1.9 (4)
O3ⁱⁱⁱ—K1—K2—C2^v	−31.42 (8)	C6—C7—C8—C9	−0.8 (4)
O3—K1—K2—C2^v	148.58 (8)	C6—C7—C8—Cl1	178.80 (19)
O1ⁱ—K1—K2—C2^v	−116.65 (6)	C7—C8—C9—C10	−1.1 (4)
O1ⁱⁱ—K1—K2—C2^v	63.35 (6)	Cl1—C8—C9—C10	179.34 (18)
F1ⁱⁱⁱ—K1—K2—C2^v	−119.67 (5)	C6—C5—C10—C9	−0.8 (4)
F1—K1—K2—C2^v	60.33 (5)	C4—C5—C10—C9	−179.5 (2)
O2ⁱ—K1—F1—C1	−90.4 (2)	C8—C9—C10—C5	1.9 (4)
O2ⁱⁱ—K1—F1—C1	167.4 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1W···O2	0.82 (3)	1.90 (3)	2.709 (2)	173 (3)
O3—H2W···O1^viii	0.87 (3)	2.06 (3)	2.843 (3)	150 (2)

Symmetry code: (viii) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[K(C₁₀H₅ClF₃O₂)(H₂O)]
M_r	306.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	30.164 (2), 8.0739 (4), 10.2696 (5)
β (°)	98.752 (2)
V (Å³)	2471.9 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.20 × 0.11 × 0.08

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.830, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	11396, 2182, 1559
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.01
No. of reflections	2182
No. of parameters	170
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1W···O2	0.82 (3)	1.90 (3)	2.709 (2)	173 (3)
O3—H2W···O1ⁱ	0.87 (3)	2.06 (3)	2.843 (3)	150 (2)

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

This work was supported by the Fundo Europeu de Desenvolvimento Regional-QREN-COMPETE through projects PEst-C/FIS/UI0036/2011, PTDC/FIS/102284/2008, PTDC/AAC-CLI/098308/2008 and PTDC/AAC-CLI/118092/2010-Fundação para a Ciência e a Tecnologia (FCT).

References

Bruker (2003). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Martín-Ramos, P., Coya, C., Alvarez, A. L., Ramos Silva, M., Zaldo, C., Paixão, J. A., Chamorro-Posada, P. & Martín-Gil, J. (2013a). J. Phys. Chem. C, 117, 10020–10030. Google Scholar
Martín-Ramos, P., Ramos-Silva, M., Coya, C., Zaldo, C., Alvarez, A. L., Alvarez-García, S., Matos-Beja, A. M. & Martín-Gil, J. (2013b). J. Mater. Chem. C, 1, 2725–2734. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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