1,1'-(Butane-1,4-di-yl)diimidazolium dinitrate.

In the title compound, C(10)H(16)N(4) (2+)·2NO(3) (-), the organic cation is located around an inversion centre. The imidazolium ring forms a dihedral angle of 62.7 (3)° with the plane defined by the C atoms of the -(CH(2))(4)- aliphatic linker. Two anions bind to the cation via three-centre N-H⋯O hydrogen bonds and thus discrete hydrogen-bonded ion triples are formed. The nitrate is approximately coplanar with the imidazolium ring to which it binds.

Related literature

For related literature, see: Gould (1986 ▶); Holman et al. (2001 ▶); Jin & Chen (2007a ▶,b ▶); Jin et al. (2007 ▶); Królikowska & Garbarczyk (2005 ▶).

Experimental

Crystal data

C10H16N4 2+·2NO3 −

M = 316.29

Monoclinic,

a = 7.788 (2) Å

b = 10.482 (3) Å

c = 9.363 (3) Å

β = 110.649 (4)°

V = 715.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 298 (2) K

0.43 × 0.40 × 0.31 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.949, T max = 0.963

3629 measured reflections

1257 independent reflections

913 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.06

1257 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063751/gk2116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063751/gk2116Isup2.hkl

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

C10H16N42+·2NO3–	F000 = 332
Mr = 316.29	Dx = 1.469 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1224 reflections
a = 7.788 (2) Å	θ = 2.8–24.0º
b = 10.482 (3) Å	µ = 0.12 mm−1
c = 9.363 (3) Å	T = 298 (2) K
β = 110.649 (4)º	Block, colourless
V = 715.3 (4) Å3	0.43 × 0.40 × 0.31 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	1257 independent reflections
Radiation source: fine-focus sealed tube	913 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.949, Tmax = 0.963	k = −12→10
3629 measured reflections	l = −11→8

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.1767P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1257 reflections	Δρmax = 0.21 e Å−3
100 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.6076 (2)	0.66149 (16)	0.79775 (17)	0.0408 (4)
N2	0.5677 (2)	0.72628 (16)	1.00094 (19)	0.0483 (5)
H2	0.5670	0.7281	1.0925	0.058*
N3	0.6173 (2)	0.84419 (17)	0.3487 (2)	0.0458 (5)
O1	0.6683 (3)	0.92237 (15)	0.27403 (18)	0.0673 (5)
O2	0.5460 (2)	0.74148 (15)	0.28855 (17)	0.0623 (5)
O3	0.6379 (3)	0.86529 (19)	0.4822 (2)	0.0934 (7)
C1	0.6268 (3)	0.6310 (2)	0.9390 (2)	0.0465 (5)
H1	0.6744	0.5546	0.9872	0.056*
C2	0.5079 (3)	0.8216 (2)	0.8959 (2)	0.0472 (5)
H2A	0.4590	0.8996	0.9098	0.057*
C3	0.5331 (3)	0.78137 (19)	0.7687 (2)	0.0440 (5)
H3	0.5051	0.8264	0.6778	0.053*
C4	0.6486 (3)	0.5788 (2)	0.6874 (2)	0.0509 (6)
H4A	0.7079	0.5016	0.7385	0.061*
H4B	0.7332	0.6223	0.6488	0.061*
C5	0.4777 (3)	0.54372 (19)	0.5556 (2)	0.0423 (5)
H5A	0.4195	0.6207	0.5030	0.051*
H5B	0.3920	0.5014	0.5941	0.051*

	U11	U22	U33	U12	U13	U23
N1	0.0393 (9)	0.0461 (10)	0.0335 (9)	−0.0006 (8)	0.0086 (7)	−0.0054 (7)
N2	0.0578 (12)	0.0535 (11)	0.0342 (9)	−0.0049 (9)	0.0167 (8)	−0.0053 (8)
N3	0.0479 (10)	0.0514 (11)	0.0390 (10)	0.0031 (9)	0.0168 (8)	0.0011 (9)
O1	0.0972 (14)	0.0527 (10)	0.0581 (10)	−0.0080 (9)	0.0349 (10)	0.0098 (8)
O2	0.0810 (12)	0.0549 (10)	0.0557 (10)	−0.0154 (9)	0.0298 (9)	−0.0085 (8)
O3	0.1370 (18)	0.1073 (16)	0.0490 (11)	−0.0433 (14)	0.0491 (11)	−0.0251 (10)
C1	0.0503 (13)	0.0439 (12)	0.0398 (12)	−0.0001 (10)	0.0090 (10)	−0.0012 (9)
C2	0.0500 (12)	0.0408 (11)	0.0470 (13)	−0.0010 (10)	0.0125 (10)	−0.0054 (10)
C3	0.0470 (12)	0.0419 (12)	0.0390 (11)	−0.0035 (10)	0.0100 (9)	0.0007 (9)
C4	0.0453 (13)	0.0594 (14)	0.0469 (13)	0.0037 (11)	0.0148 (10)	−0.0142 (10)
C5	0.0407 (11)	0.0446 (11)	0.0409 (11)	−0.0020 (9)	0.0136 (9)	−0.0062 (9)

N1—C1	1.317 (2)	C2—C3	1.342 (3)
N1—C3	1.371 (3)	C2—H2A	0.9300
N1—C4	1.467 (2)	C3—H3	0.9300
N2—C1	1.316 (3)	C4—C5	1.507 (3)
N2—C2	1.364 (3)	C4—H4A	0.9700
N2—H2	0.8600	C4—H4B	0.9700
N3—O3	1.223 (2)	C5—C5i	1.518 (4)
N3—O1	1.231 (2)	C5—H5A	0.9700
N3—O2	1.251 (2)	C5—H5B	0.9700
C1—H1	0.9300
C1—N1—C3	108.15 (16)	C2—C3—N1	107.24 (18)
C1—N1—C4	126.02 (18)	C2—C3—H3	126.4
C3—N1—C4	125.73 (17)	N1—C3—H3	126.4
C1—N2—C2	108.78 (18)	N1—C4—C5	111.83 (16)
C1—N2—H2	125.6	N1—C4—H4A	109.3
C2—N2—H2	125.6	C5—C4—H4A	109.3
O3—N3—O1	120.54 (19)	N1—C4—H4B	109.3
O3—N3—O2	119.56 (18)	C5—C4—H4B	109.3
O1—N3—O2	119.90 (18)	H4A—C4—H4B	107.9
N2—C1—N1	108.97 (18)	C4—C5—C5i	111.1 (2)
N2—C1—H1	125.5	C4—C5—H5A	109.4
N1—C1—H1	125.5	C5i—C5—H5A	109.4
C3—C2—N2	106.86 (19)	C4—C5—H5B	109.4
C3—C2—H2A	126.6	C5i—C5—H5B	109.4
N2—C2—H2A	126.6	H5A—C5—H5B	108.0
C2—N2—C1—N1	0.1 (2)	C1—N1—C3—C2	−0.1 (2)
C3—N1—C1—N2	0.0 (2)	C4—N1—C3—C2	176.60 (18)
C4—N1—C1—N2	−176.70 (17)	C1—N1—C4—C5	113.5 (2)
C1—N2—C2—C3	−0.2 (2)	C3—N1—C4—C5	−62.7 (3)
N2—C2—C3—N1	0.2 (2)	N1—C4—C5—C5i	−179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ii	0.86	2.59	3.157 (2)	124
N2—H2···O2ii	0.86	1.90	2.762 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.59	3.157 (2)	124
N2—H2⋯O2i	0.86	1.90	2.762 (2)	175

Symmetry code: (i) .