Bis(1-ethyl-3-methyl-imidazolium) 3,6-diselanyl-idene-1,2,4,5-tetra-selena-3,6-diphospha-cyclo-hexane-3,6-di-selen-olate.

In the title compound, 2C6H11N2 (+)·P2Se8 (2-) or [EMIM]2P2Se8 (EMIM = 1-ethyl-3-methyl-imidazolium), the anions, located about inversion centers between EMIM cations, exhibit a cyclo-hexane-like chair conformation. The cations are found in columns along the a axis, with centroid-centroid distances of 3.8399 (3) and 4.7530 (2) Å. The observed P-Se distances and Se-P-Se angles agree with other salts of this anion.

Related literature

For similar seleno­phosphate compounds, see: Biswas et al. (2010 ▶); Lin et al. (2012 ▶). For ionothermal reactions in room-temperature ionic liquids, see: Morris (2009 ▶); Parnham & Morris (2007 ▶); Cody et al. (2012 ▶). For the preparation of EMIM(BF4), see: Egashira et al. (2006 ▶). For the structure of the P2Se8 2− anion, see: Zhao et al. (1992 ▶); Rotter et al. (2008 ▶). For π–π inter­actions between imidazolium cations, see: Wilkes & Zaworotko (1993 ▶).

Experimental

Crystal data

2C6H11N2 +·P2Se8 2−

M = 915.96

Triclinic,

a = 7.8885 (4) Å

b = 9.3783 (4) Å

c = 9.8039 (5) Å

α = 110.390 (3)°

β = 96.395 (4)°

γ = 102.992 (5)°

V = 648.00 (5) Å3

Z = 1

Mo Kα radiation

μ = 11.41 mm−1

T = 293 K

0.19 × 0.07 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: Gaussian [JANA2006 (Petříček et al., 2006 ▶) and X-SHAPE (Stoe & Cie, 1998 ▶)] T min = 0.204, T max = 0.754

22118 measured reflections

3719 independent reflections

2622 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.063

S = 1.02

3719 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.55 e Å−3

Data collection: COLLECT (Hooft, 2009 ▶); cell refinement: COLLECT; data reduction: COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813020308/nc2314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020308/nc2314Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020308/nc2314Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020308/nc2314Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C6H11N2+·P2Se82−	Z = 1
Mr = 915.96	F(000) = 424
Triclinic, P1	Dx = 2.347 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8885 (4) Å	Cell parameters from 3719 reflections
b = 9.3783 (4) Å	θ = 6.5–30.0°
c = 9.8039 (5) Å	µ = 11.41 mm−1
α = 110.390 (3)°	T = 293 K
β = 96.395 (4)°	Plate, yellow
γ = 102.992 (5)°	0.19 × 0.07 × 0.03 mm
V = 648.00 (5) Å3

Nonius KappaCCD diffractometer	3719 independent reflections
Radiation source: fine-focus sealed tube	2622 reflections with I > 2σ(I)
Unknown monochromator	Rint = 0.072
ω scans	θmax = 30.0°, θmin = 6.5°
Absorption correction: gaussian [JANA2006 (Petříček et al., 2006) and X-SHAPE (Stoe & Cie, 1998)]	h = −10→11
Tmin = 0.204, Tmax = 0.754	k = −13→13
22118 measured reflections	l = −13→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0252P)2 + 0.2292P] where P = (Fo2 + 2Fc2)/3
3719 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Experimental. A set of 280 frames were collected with a rotation of 2° per frame and an exposure time of 190 s; the crystal to detector distance was 25.00 mm. Refinements were done with the SHELXTL97 (Sheldrick, 2008) software package; absorption correction was made with the program Jana2006 (Petricek et al., 2006) using the program X-SHAPE (Stoe & Cie, 1998).

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.

	x	y	z	Uiso*/Ueq
P1	0.62769 (11)	−0.10004 (9)	0.13027 (9)	0.03455 (17)
Se1	0.38273 (4)	−0.24755 (3)	−0.05425 (4)	0.04208 (9)
Se2	0.21381 (4)	−0.06847 (4)	−0.03916 (4)	0.04234 (9)
Se3	0.77764 (6)	−0.26777 (5)	0.09996 (4)	0.05519 (11)
Se4	0.56642 (5)	0.01558 (4)	0.33743 (4)	0.04503 (10)
N1	0.2827 (4)	0.4858 (3)	0.3773 (3)	0.0413 (6)
N2	0.2005 (3)	0.2740 (3)	0.4218 (3)	0.0422 (6)
C1	0.2281 (4)	0.3279 (4)	0.3154 (4)	0.0415 (7)
H1	0.2122	0.2661	0.2148	0.050*
C2	0.2379 (5)	0.4007 (5)	0.5542 (4)	0.0530 (9)
H2	0.2298	0.3961	0.6465	0.064*
C3	0.2884 (5)	0.5333 (4)	0.5270 (4)	0.0525 (9)
H3	0.3210	0.6372	0.5965	0.063*
C4	0.3182 (5)	0.5911 (4)	0.2952 (4)	0.0486 (8)
H4A	0.3597	0.5382	0.2068	0.058*
H4B	0.4115	0.6869	0.3572	0.058*
C5	0.1558 (6)	0.6340 (6)	0.2513 (6)	0.0735 (13)
H5A	0.1832	0.7026	0.1986	0.110*
H5B	0.1156	0.6877	0.3388	0.110*
H5C	0.0641	0.5395	0.1883	0.110*
C6	0.1325 (5)	0.1069 (4)	0.3983 (5)	0.0606 (10)
H6A	0.1248	0.0980	0.4922	0.091*
H6B	0.2114	0.0496	0.3527	0.091*
H6C	0.0165	0.0634	0.3345	0.091*

	U11	U22	U33	U12	U13	U23
P1	0.0454 (4)	0.0353 (4)	0.0258 (4)	0.0132 (3)	0.0065 (3)	0.0144 (3)
Se1	0.0560 (2)	0.03274 (15)	0.03188 (17)	0.00568 (13)	0.00294 (14)	0.01201 (13)
Se2	0.03936 (17)	0.05217 (19)	0.03963 (19)	0.00924 (13)	0.00866 (14)	0.02474 (16)
Se3	0.0774 (3)	0.0598 (2)	0.0454 (2)	0.0411 (2)	0.01621 (19)	0.02586 (19)
Se4	0.0639 (2)	0.04233 (17)	0.02882 (17)	0.01506 (15)	0.01340 (15)	0.01247 (14)
N1	0.0472 (15)	0.0410 (14)	0.0361 (15)	0.0097 (11)	0.0087 (12)	0.0172 (12)
N2	0.0435 (14)	0.0439 (15)	0.0431 (16)	0.0089 (11)	0.0079 (12)	0.0239 (13)
C1	0.0461 (18)	0.0424 (16)	0.0338 (17)	0.0084 (13)	0.0078 (14)	0.0147 (14)
C2	0.063 (2)	0.066 (2)	0.036 (2)	0.0179 (18)	0.0138 (17)	0.0268 (19)
C3	0.071 (2)	0.0468 (18)	0.0329 (18)	0.0121 (17)	0.0126 (17)	0.0101 (16)
C4	0.054 (2)	0.0459 (18)	0.052 (2)	0.0092 (15)	0.0174 (17)	0.0277 (17)
C5	0.065 (3)	0.095 (3)	0.095 (4)	0.030 (2)	0.025 (2)	0.069 (3)
C6	0.064 (2)	0.051 (2)	0.075 (3)	0.0095 (17)	0.013 (2)	0.038 (2)

P1—Se4	2.1104 (8)	C2—C3	1.345 (5)
P1—Se3	2.1334 (8)	C2—H2	0.9300
P1—Se1	2.2794 (9)	C3—H3	0.9300
P1—Se2i	2.2809 (8)	C4—C5	1.489 (5)
Se1—Se2	2.3442 (5)	C4—H4A	0.9700
Se2—P1i	2.2809 (8)	C4—H4B	0.9700
N1—C1	1.332 (4)	C5—H5A	0.9600
N1—C3	1.370 (4)	C5—H5B	0.9600
N1—C4	1.477 (4)	C5—H5C	0.9600
N2—C1	1.327 (4)	C6—H6A	0.9600
N2—C2	1.366 (4)	C6—H6B	0.9600
N2—C6	1.463 (4)	C6—H6C	0.9600
C1—H1	0.9300
Se4—P1—Se3	122.19 (4)	C2—C3—H3	126.6
Se4—P1—Se1	113.49 (4)	N1—C3—H3	126.6
Se3—P1—Se1	100.04 (3)	N1—C4—C5	111.4 (3)
Se4—P1—Se2i	113.90 (4)	N1—C4—H4A	109.3
Se3—P1—Se2i	100.49 (3)	C5—C4—H4A	109.3
Se1—P1—Se2i	104.32 (3)	N1—C4—H4B	109.3
P1—Se1—Se2	102.89 (2)	C5—C4—H4B	109.3
P1i—Se2—Se1	102.37 (2)	H4A—C4—H4B	108.0
C1—N1—C3	108.8 (3)	C4—C5—H5A	109.5
C1—N1—C4	125.1 (3)	C4—C5—H5B	109.5
C3—N1—C4	126.0 (3)	H5A—C5—H5B	109.5
C1—N2—C2	108.5 (3)	C4—C5—H5C	109.5
C1—N2—C6	125.1 (3)	H5A—C5—H5C	109.5
C2—N2—C6	126.3 (3)	H5B—C5—H5C	109.5
N2—C1—N1	108.3 (3)	N2—C6—H6A	109.5
N2—C1—H1	125.9	N2—C6—H6B	109.5
N1—C1—H1	125.9	H6A—C6—H6B	109.5
C3—C2—N2	107.8 (3)	N2—C6—H6C	109.5
C3—C2—H2	126.1	H6A—C6—H6C	109.5
N2—C2—H2	126.1	H6B—C6—H6C	109.5
C2—C3—N1	106.7 (3)

P1—Se4	2.1104 (8)
P1—Se3	2.1334 (8)
P1—Se1	2.2794 (9)
P1—Se2i	2.2809 (8)
Se1—Se2	2.3442 (5)

Se4—P1—Se3	122.19 (4)
Se4—P1—Se1	113.49 (4)
Se3—P1—Se1	100.04 (3)
Se4—P1—Se2i	113.90 (4)
Se3—P1—Se2i	100.49 (3)
Se1—P1—Se2i	104.32 (3)
P1—Se1—Se2	102.89 (2)
P1i—Se2—Se1	102.37 (2)

Symmetry code: (i) .