(18-Crown-6)potassium(I) di-phenyl-stibate(-1).

Red crystals of the title salt, [K(C12H24O6)][Sb(C6H5)2], were obtained by the reaction of SbPh3, KSnBi and 18-crown-6 in liquid ammonia. The asymmetric unit contains one half of a [K(18-crown-6)](+) cation and one half of an SbPh2 (-) anion, with the central element lying on a twofold axis and a centre of inversion, respectively. In the crystal structure, the sequestered potassium cations show weak inter-actions with the π-electrons of the phenyl groups of the SbPh2 (-) anion [shortest K⋯C distances = 3.190 (2) and 3.441 (2) Å], leading to one-dimensional strands along the crystallographic c axis. These strands are aligned in a pseudo-hexa-gonal packing perpendicular to the ab plane.

Related literature

For literature focusing on mechanisms of crystallization and inter­molecular inter­actions or di­phenyl­stibide as a nucleophile, see: Desiraju (2007 ▶); Ugrinov & Sevov (2003 ▶). For a related compound, see Effendy et al. (1997 ▶).

Experimental

Crystal data

[K(C12H24O6)][Sb(C6H5)2]

M = 579.36

Monoclinic,

a = 15.6933 (9) Å

b = 9.2655 (3) Å

c = 19.1321 (10) Å

β = 112.654 (6)°

V = 2567.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.27 mm−1

T = 123 K

0.47 × 0.27 × 0.15 mm

Data collection

Agilent SuperNova (Single source at offset, Eos) diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.726, T max = 0.863

4194 measured reflections

2592 independent reflections

2297 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.053

S = 1.08

2592 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.56 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶; Bourhis et al., 2011 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814013282/ff2129sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013282/ff2129Isup2.hkl

CCDC reference: 1007141

Additional supporting information: crystallographic information; 3D view; checkCIF report

[K(C12H24O6)][Sb(C6H5)2]	F(000) = 1184
Mr = 579.36	Dx = 1.499 Mg m−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 15.6933 (9) Å	Cell parameters from 1900 reflections
b = 9.2655 (3) Å	θ = 3.4–28.0°
c = 19.1321 (10) Å	µ = 1.27 mm−1
β = 112.654 (6)°	T = 123 K
V = 2567.3 (2) Å3	Block, clear reddish red
Z = 4	0.47 × 0.27 × 0.15 mm

Agilent SuperNova (Single source at offset, Eos) diffractometer	2297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
phi and ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]	h = −18→19
Tmin = 0.726, Tmax = 0.863	k = −11→10
4194 measured reflections	l = −15→23
2592 independent reflections

Refinement on F2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023	H-atom parameters constrained
wR(F2) = 0.053	w = 1/[σ2(Fo2) + (0.019P)2 + 0.7904P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2592 reflections	Δρmax = 0.39 e Å−3
147 parameters	Δρmin = −0.56 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
Sb1	0.7500	1.08580 (2)	1.0000	0.02163 (8)
K1	0.7500	0.7500	0.7500	0.02190 (15)
O2	0.62864 (10)	0.83061 (17)	0.60590 (8)	0.0237 (3)
O3	0.74551 (10)	1.03820 (17)	0.70288 (8)	0.0241 (4)
O1	0.60734 (10)	0.56706 (17)	0.66609 (8)	0.0225 (3)
C1	0.67008 (14)	0.9316 (2)	0.91614 (11)	0.0191 (5)
C10	0.54293 (15)	0.7554 (3)	0.57688 (12)	0.0278 (5)
H10A	0.5106	0.7774	0.5236	0.033*
H10B	0.5045	0.7855	0.6036	0.033*
C4	0.56109 (15)	0.7424 (3)	0.79930 (12)	0.0279 (5)
H4	0.5263	0.6798	0.7609	0.033*
C11	0.61898 (16)	0.9803 (3)	0.58922 (12)	0.0292 (5)
H11A	0.5781	1.0236	0.6106	0.035*
H11B	0.5924	0.9947	0.5348	0.035*
C3	0.59436 (14)	0.6990 (3)	0.87465 (12)	0.0249 (5)
H3	0.5813	0.6068	0.8870	0.030*
C7	0.66870 (16)	0.3883 (3)	0.76152 (13)	0.0286 (5)
H7A	0.6253	0.4205	0.7831	0.034*
H7B	0.6779	0.2853	0.7701	0.034*
C2	0.64697 (14)	0.7928 (3)	0.93162 (12)	0.0215 (5)
H2	0.6675	0.7622	0.9817	0.026*
C5	0.58069 (15)	0.8799 (3)	0.78264 (12)	0.0283 (6)
H5	0.5577	0.9111	0.7326	0.034*
C9	0.56103 (15)	0.5973 (3)	0.58705 (12)	0.0256 (5)
H9A	0.5032	0.5446	0.5668	0.031*
H9B	0.5991	0.5670	0.5600	0.031*
C8	0.63067 (16)	0.4186 (3)	0.67829 (13)	0.0267 (5)
H8A	0.6763	0.3946	0.6574	0.032*
H8B	0.5762	0.3600	0.6530	0.032*
C12	0.71193 (16)	1.0495 (3)	0.62224 (12)	0.0276 (5)
H12A	0.7541	1.0016	0.6037	0.033*
H12B	0.7075	1.1502	0.6074	0.033*
C6	0.63440 (15)	0.9725 (3)	0.83964 (12)	0.0248 (5)
H6	0.6471	1.0645	0.8267	0.030*

	U11	U22	U33	U12	U13	U23
Sb1	0.02653 (12)	0.01591 (12)	0.02407 (12)	0.000	0.01153 (9)	0.000
K1	0.0173 (3)	0.0167 (3)	0.0253 (3)	−0.0019 (3)	0.0011 (3)	0.0031 (3)
O2	0.0198 (8)	0.0233 (9)	0.0239 (8)	0.0032 (7)	0.0040 (6)	0.0018 (7)
O3	0.0268 (8)	0.0216 (9)	0.0252 (8)	−0.0006 (7)	0.0114 (7)	0.0043 (7)
O1	0.0253 (8)	0.0221 (9)	0.0194 (7)	−0.0013 (7)	0.0078 (6)	−0.0053 (6)
C1	0.0175 (10)	0.0202 (12)	0.0218 (10)	0.0044 (9)	0.0098 (9)	−0.0001 (9)
C10	0.0185 (11)	0.0411 (16)	0.0187 (11)	0.0017 (11)	0.0016 (9)	−0.0024 (11)
C4	0.0201 (11)	0.0368 (15)	0.0276 (12)	0.0002 (11)	0.0102 (9)	−0.0106 (11)
C11	0.0305 (13)	0.0315 (14)	0.0248 (12)	0.0122 (12)	0.0098 (10)	0.0096 (11)
C3	0.0192 (11)	0.0213 (12)	0.0367 (13)	−0.0001 (10)	0.0134 (10)	−0.0017 (10)
C7	0.0311 (13)	0.0200 (13)	0.0400 (14)	−0.0053 (11)	0.0195 (11)	0.0003 (11)
C2	0.0200 (11)	0.0240 (12)	0.0213 (11)	0.0019 (10)	0.0088 (9)	0.0032 (9)
C5	0.0230 (12)	0.0424 (16)	0.0192 (11)	0.0038 (12)	0.0080 (9)	0.0020 (11)
C9	0.0221 (11)	0.0327 (14)	0.0200 (11)	−0.0061 (11)	0.0058 (9)	−0.0080 (10)
C8	0.0308 (12)	0.0194 (12)	0.0338 (12)	−0.0096 (11)	0.0167 (10)	−0.0076 (10)
C12	0.0356 (13)	0.0236 (13)	0.0286 (12)	0.0084 (11)	0.0178 (10)	0.0090 (10)
C6	0.0245 (12)	0.0264 (13)	0.0251 (11)	0.0020 (11)	0.0114 (9)	0.0041 (10)

Sb1—C1	2.154 (2)	C4—C5	1.376 (3)
K1—O2	2.7823 (14)	C11—H11A	0.9700
K1—O3	2.8106 (16)	C11—H11B	0.9700
K1—O1	2.7738 (15)	C11—C12	1.493 (3)
K1—C4	3.441 (2)	C3—H3	0.9300
K1—C5	3.190 (2)	C3—C2	1.390 (3)
O2—C10	1.424 (3)	C7—H7A	0.9700
O2—C11	1.418 (3)	C7—H7B	0.9700
O3—C7i	1.426 (3)	C7—C8	1.496 (3)
O3—C12	1.429 (2)	C2—H2	0.9300
O1—C9	1.431 (2)	C5—H5	0.9300
O1—C8	1.419 (3)	C5—C6	1.389 (3)
C1—C2	1.399 (3)	C9—H9A	0.9700
C1—C6	1.403 (3)	C9—H9B	0.9700
C10—H10A	0.9700	C8—H8A	0.9700
C10—H10B	0.9700	C8—H8B	0.9700
C10—C9	1.490 (3)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C4—C3	1.390 (3)	C6—H6	0.9300
C1—Sb1—C1ii	96.89 (12)	O2—C10—H10A	109.9
O2—K1—O2i	180.00 (6)	O2—C10—H10B	109.9
O2i—K1—O3i	60.27 (4)	O2—C10—C9	109.03 (18)
O2i—K1—O3	119.73 (4)	H10A—C10—H10B	108.3
O2—K1—O3i	119.73 (4)	C9—C10—H10A	109.9
O2—K1—O3	60.27 (4)	C9—C10—H10B	109.9
O2—K1—C4	86.78 (5)	K1—C4—H4	95.9
O2—K1—C4i	93.22 (5)	C3—C4—K1	105.73 (13)
O2i—K1—C4	93.22 (5)	C3—C4—H4	120.7
O2i—K1—C4i	86.78 (5)	C5—C4—K1	67.95 (13)
O2—K1—C5	77.81 (5)	C5—C4—H4	120.7
O2—K1—C5i	102.19 (5)	C5—C4—C3	118.7 (2)
O2i—K1—C5i	77.81 (5)	O2—C11—H11A	109.9
O2i—K1—C5	102.19 (5)	O2—C11—H11B	109.9
O3—K1—O3i	180.0	O2—C11—C12	108.82 (18)
O3—K1—C4i	79.08 (5)	H11A—C11—H11B	108.3
O3i—K1—C4i	100.92 (5)	C12—C11—H11A	109.9
O3—K1—C4	100.92 (5)	C12—C11—H11B	109.9
O3i—K1—C4	79.08 (5)	C4—C3—H3	119.8
O3—K1—C5i	102.44 (6)	C2—C3—C4	120.3 (2)
O3i—K1—C5i	77.56 (6)	C2—C3—H3	119.8
O3i—K1—C5	102.44 (6)	O3i—C7—H7A	109.8
O3—K1—C5	77.56 (6)	O3i—C7—H7B	109.8
O1—K1—O2	59.91 (4)	O3i—C7—C8	109.56 (18)
O1—K1—O2i	120.09 (5)	H7A—C7—H7B	108.2
O1i—K1—O2i	59.91 (5)	C8—C7—H7A	109.8
O1i—K1—O2	120.09 (5)	C8—C7—H7B	109.8
O1i—K1—O3	61.31 (4)	C1—C2—H2	118.9
O1—K1—O3i	61.31 (4)	C3—C2—C1	122.2 (2)
O1i—K1—O3i	118.69 (4)	C3—C2—H2	118.9
O1—K1—O3	118.69 (4)	K1—C5—H5	86.5
O1i—K1—O1	180.0	C4—C5—K1	88.49 (14)
O1i—K1—C4	116.26 (5)	C4—C5—H5	119.6
O1—K1—C4i	116.26 (5)	C4—C5—C6	120.8 (2)
O1—K1—C4	63.74 (5)	C6—C5—K1	95.02 (14)
O1i—K1—C4i	63.74 (5)	C6—C5—H5	119.6
O1—K1—C5	78.25 (5)	O1—C9—C10	108.91 (18)
O1i—K1—C5i	78.25 (5)	O1—C9—H9A	109.9
O1i—K1—C5	101.75 (5)	O1—C9—H9B	109.9
O1—K1—C5i	101.75 (5)	C10—C9—H9A	109.9
C4—K1—C4i	180.00 (10)	C10—C9—H9B	109.9
C5—K1—C4	23.57 (6)	H9A—C9—H9B	108.3
C5i—K1—C4i	23.57 (6)	O1—C8—C7	109.22 (18)
C5—K1—C4i	156.43 (6)	O1—C8—H8A	109.8
C5i—K1—C4	156.43 (6)	O1—C8—H8B	109.8
C5i—K1—C5	180.0	C7—C8—H8A	109.8
C10—O2—K1	115.99 (12)	C7—C8—H8B	109.8
C11—O2—K1	117.29 (12)	H8A—C8—H8B	108.3
C11—O2—C10	112.83 (17)	O3—C12—C11	108.62 (18)
C7i—O3—K1	113.46 (12)	O3—C12—H12A	110.0
C7i—O3—C12	111.61 (16)	O3—C12—H12B	110.0
C12—O3—K1	111.65 (13)	C11—C12—H12A	110.0
C9—O1—K1	117.40 (12)	C11—C12—H12B	110.0
C8—O1—K1	113.42 (12)	H12A—C12—H12B	108.3
C8—O1—C9	110.95 (17)	C1—C6—H6	119.0
C2—C1—Sb1	125.20 (15)	C5—C6—C1	122.0 (2)
C2—C1—C6	115.9 (2)	C5—C6—H6	119.0
C6—C1—Sb1	118.81 (17)

Table 1

Selected bond lengths (Å)

Sb1—C1	2.154 (2)
K1—O2	2.7823 (14)
K1—O3	2.8106 (16)
K1—O1	2.7738 (15)