3,3'-(Butane-1,4-di-yl)diimidazole-1,1'-diium bis-(triiodide).

The cations and anions of the salt, C(10)H(16)N(4) (2+)·2I(3) (-), are linked by N-H⋯I hydrogen bonds and π-π stacking inter-actions(with interplanar distances of 3.575 and 3.528 Å) into a three-dimensional supra-molecular network. The asymmetric unit contains two anions and two half-cations; each cation is centrosymmetric.

Related literature

For literature on 1,1′-(1,4-butanedi­yl)diimidazole, see: Ma et al. (2003 ▶). For the structure of another 1,1′-(1,4-butanedi­yl)diimidazole-3,3′-diium salt, see: Yu et al. (2008 ▶).

Experimental

Crystal data

C10H16N4 2+·2I3 −

M = 953.67

Triclinic,

a = 8.4753 (17) Å

b = 9.7177 (19) Å

c = 14.110 (3) Å

α = 95.77 (3)°

β = 92.82 (3)°

γ = 107.17 (3)°

V = 1100.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 8.46 mm−1

T = 291 (2) K

0.21 × 0.20 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.266, T max = 0.306 (expected range = 0.189–0.218)

8492 measured reflections

3831 independent reflections

3045 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 1.10

3831 reflections

178 parameters

H-atom parameters constrained

Δρmax = 1.19 e Å−3

Δρmin = −0.86 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022393/ng2463sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022393/ng2463Isup2.hkl

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

C10H16N42+·2I3–	Z = 2
Mr = 953.67	F000 = 844
Triclinic, P1	Dx = 2.877 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.4753 (17) Å	Cell parameters from 7434 reflections
b = 9.7177 (19) Å	θ = 3.0–27.5º
c = 14.110 (3) Å	µ = 8.46 mm−1
α = 95.77 (3)º	T = 291 (2) K
β = 92.82 (3)º	Block, yellow
γ = 107.17 (3)º	0.21 × 0.20 × 0.18 mm
V = 1100.9 (4) Å3

Rigaku R-AXIS RAPID diffractometer	3831 independent reflections
Radiation source: fine-focus sealed tube	3045 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 291(2) K	θmax = 25.0º
ω scans	θmin = 3.0º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.266, Tmax = 0.307	k = −11→11
8492 measured reflections	l = −16→16

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0254P)2 + 5.2161P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3831 reflections	Δρmax = 1.19 e Å−3
178 parameters	Δρmin = −0.86 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
C1	0.6046 (11)	0.3684 (10)	0.5506 (6)	0.049 (2)
H1	0.7142	0.3830	0.5369	0.058*
C2	0.5511 (12)	0.4469 (11)	0.6176 (7)	0.055 (2)
H2	0.6159	0.5268	0.6585	0.066*
C3	0.3377 (12)	0.2777 (12)	0.5469 (7)	0.056 (2)
H4	0.2293	0.2191	0.5305	0.067*
C4	0.4772 (13)	0.1552 (11)	0.4282 (6)	0.057 (3)
H6	0.5458	0.2028	0.3808	0.069*
H5	0.3664	0.1090	0.3977	0.069*
C5	0.5466 (12)	0.0400 (11)	0.4628 (7)	0.062 (3)
H8	0.5474	−0.0293	0.4085	0.075*
H7	0.6605	0.0860	0.4884	0.075*
C6	1.0068 (12)	0.3316 (11)	0.1048 (7)	0.055 (2)
H9	0.9362	0.2915	0.1499	0.066*
C7	1.1312 (11)	0.4573 (11)	0.1195 (8)	0.057 (3)
H10	1.1636	0.5208	0.1758	0.068*
C8	1.1230 (13)	0.3611 (11)	−0.0302 (7)	0.056 (3)
H12	1.1490	0.3477	−0.0930	0.067*
C9	0.8858 (8)	0.1352 (8)	−0.0341 (6)	0.055 (2)
H13	0.8975	0.1278	−0.1023	0.066*
H14	0.7734	0.1358	−0.0247	0.066*
C10	0.9139 (8)	0.0029 (8)	0.0049 (6)	0.079 (4)
H15	0.8923	0.0055	0.0718	0.094*
H16	0.8364	−0.0844	−0.0293	0.094*
I1	0.55146 (9)	0.37444 (7)	0.15451 (5)	0.05732 (19)
I2	0.54230 (7)	0.06704 (6)	0.16015 (4)	0.04222 (15)
I3	0.53942 (8)	−0.22804 (7)	0.16387 (5)	0.0602 (2)
I4	0.96410 (8)	0.34498 (8)	0.37380 (5)	0.0608 (2)
I5	0.99004 (7)	0.05335 (7)	0.33765 (4)	0.05118 (17)
I6	1.03499 (9)	−0.23842 (8)	0.31071 (5)	0.0636 (2)
N1	1.0024 (9)	0.2733 (8)	0.0121 (5)	0.0471 (18)
N2	1.1981 (10)	0.4712 (9)	0.0356 (6)	0.060 (2)
H11	1.2906	0.5258	0.0211	0.072*
N3	0.4708 (8)	0.2639 (8)	0.5063 (5)	0.0443 (17)
N4	0.3853 (10)	0.3886 (9)	0.6146 (6)	0.058 (2)
H3	0.3111	0.4094	0.6480	0.070*

	U11	U22	U33	U12	U13	U23
C1	0.039 (5)	0.053 (6)	0.048 (5)	0.005 (4)	0.007 (4)	0.002 (5)
C2	0.054 (6)	0.052 (6)	0.049 (6)	0.006 (5)	−0.003 (5)	−0.002 (5)
C3	0.050 (6)	0.068 (7)	0.052 (6)	0.021 (5)	0.009 (5)	0.007 (5)
C4	0.062 (6)	0.074 (7)	0.038 (5)	0.027 (6)	0.005 (5)	−0.001 (5)
C5	0.060 (6)	0.063 (7)	0.067 (7)	0.023 (6)	0.017 (5)	0.002 (5)
C6	0.052 (6)	0.067 (7)	0.049 (6)	0.026 (6)	0.004 (5)	−0.003 (5)
C7	0.039 (5)	0.049 (6)	0.072 (7)	0.005 (5)	−0.010 (5)	−0.012 (5)
C8	0.067 (6)	0.061 (7)	0.050 (6)	0.034 (6)	0.006 (5)	0.011 (5)
C9	0.051 (5)	0.045 (6)	0.060 (6)	0.003 (5)	−0.006 (5)	0.006 (5)
C10	0.056 (6)	0.037 (6)	0.121 (10)	−0.018 (5)	−0.001 (7)	0.009 (6)
I1	0.0714 (4)	0.0472 (4)	0.0598 (4)	0.0265 (3)	0.0108 (3)	0.0079 (3)
I2	0.0397 (3)	0.0447 (3)	0.0383 (3)	0.0090 (3)	0.0015 (2)	−0.0012 (2)
I3	0.0601 (4)	0.0393 (4)	0.0767 (5)	0.0106 (3)	−0.0034 (3)	0.0040 (3)
I4	0.0584 (4)	0.0562 (4)	0.0616 (4)	0.0098 (3)	0.0076 (3)	−0.0007 (3)
I5	0.0415 (3)	0.0630 (4)	0.0443 (3)	0.0107 (3)	−0.0010 (3)	0.0020 (3)
I6	0.0660 (4)	0.0729 (5)	0.0604 (4)	0.0338 (4)	0.0089 (3)	0.0062 (4)
N1	0.051 (4)	0.048 (5)	0.049 (5)	0.022 (4)	0.004 (4)	0.014 (4)
N2	0.049 (5)	0.061 (6)	0.075 (6)	0.024 (4)	0.006 (5)	0.017 (5)
N3	0.040 (4)	0.048 (5)	0.043 (4)	0.009 (4)	0.003 (3)	0.008 (3)
N4	0.054 (5)	0.065 (6)	0.055 (5)	0.015 (4)	0.015 (4)	0.004 (4)

C1—C2	1.335 (13)	C7—N2	1.340 (13)
C1—N3	1.354 (11)	C7—H10	0.9300
C1—H1	0.9300	C8—N1	1.332 (12)
C2—N4	1.348 (12)	C8—N2	1.324 (12)
C2—H2	0.9300	C8—H12	0.9300
C3—N4	1.317 (12)	C9—N1	1.477 (10)
C3—N3	1.326 (11)	C9—C10	1.5246
C3—H4	0.9300	C9—H13	0.9700
C4—N3	1.462 (11)	C9—H14	0.9700
C4—C5	1.519 (13)	C10—C10ii	1.489
C4—H6	0.9700	C10—H15	0.9700
C4—H5	0.9700	C10—H16	0.9700
C5—C5i	1.487 (19)	I1—I2	2.9745 (10)
C5—H8	0.9700	I2—I3	2.8662 (10)
C5—H7	0.9700	I4—I5	2.9031 (11)
C6—C7	1.347 (13)	I5—I6	2.9604 (11)
C6—N1	1.367 (11)	N2—H11	0.8544
C6—H9	0.9300	N4—H3	0.8628
C2—C1—N3	107.7 (8)	N1—C8—H12	127.1
C2—C1—H1	126.2	N2—C8—H12	127.1
N3—C1—H1	126.2	N1—C9—C10	112.9
C1—C2—N4	107.1 (9)	N1—C9—H13	109.0
C1—C2—H2	126.5	C10—C9—H13	109.0
N4—C2—H2	126.5	N1—C9—H14	109.0
N4—C3—N3	108.2 (9)	C10—C9—H14	109.0
N4—C3—H4	125.9	H13—C9—H14	107.8
N3—C3—H4	125.9	C10ii—C10—C9	112.0 (5)
N3—C4—C5	112.1 (8)	C10ii—C10—H15	109.2
N3—C4—H6	109.2	C9—C10—H15	109.2
C5—C4—H6	109.2	C10ii—C10—H16	109.2
N3—C4—H5	109.2	C9—C10—H16	109.2
C5—C4—H5	109.2	H15—C10—H16	107.9
H6—C4—H5	107.9	I3—I2—I1	178.89 (3)
C5i—C5—C4	114.5 (10)	I4—I5—I6	176.21 (3)
C5i—C5—H8	108.6	C8—N1—C6	108.7 (9)
C4—C5—H8	108.6	C8—N1—C9	125.1 (8)
C5i—C5—H7	108.6	C6—N1—C9	126.2 (8)
C4—C5—H7	108.6	C8—N2—C7	112.3 (9)
H8—C5—H7	107.6	C8—N2—H11	114.7
C7—C6—N1	108.1 (9)	C7—N2—H11	131.3
C7—C6—H9	125.9	C3—N3—C1	108.0 (8)
N1—C6—H9	125.9	C3—N3—C4	127.3 (8)
C6—C7—N2	105.0 (9)	C1—N3—C4	124.6 (7)
C6—C7—H10	127.5	C3—N4—C2	109.0 (8)
N2—C7—H10	127.5	C3—N4—H3	118.4
N1—C8—N2	105.9 (9)	C2—N4—H3	132.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H11···I3iii	0.85	3.14	3.690 (9)	124
N2—H11···I1iv	0.85	2.99	3.666 (9)	138
N4—H3···I1v	0.86	3.25	3.714 (9)	116
N4—H3···I6i	0.86	3.03	3.679 (8)	134
C6—H9···I4	0.93	3.13	3.823 (10)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H11⋯I3i	0.85	3.14	3.690 (9)	124
N2—H11⋯I1ii	0.85	2.99	3.666 (9)	138
N4—H3⋯I1iii	0.86	3.25	3.714 (9)	116
N4—H3⋯I6iv	0.86	3.03	3.679 (8)	134

Symmetry codes: (i) ; (ii) ; (iii) , ; (iv) .