4-tert-Butyl-pyridinium triiodide-4-tert-butyl-pyridine (1/1).

The title compound, C(9)H(14)N(+)·I(3) (-)·C(9)H(13)N, consists of monoprotonated 4-tert-butyl-pyridinium cations and triiodide anions. The triiodide ion has near-symmetric linear geometry, with bond lengths of 2.9105 (4) Å (I-I) and a bond angle of 177.55 (3)° (I-I-I). For this room-temperature structure, the butyl group on the pyridine ring is disordered and has been treated as a rigid rotator, modeled in three separate positions with 1/3, 1/3, 1/3 occupancies. The cations assemble into dimeric forms by way of N-H⋯N hydrogen bonds.

Related literature

For applications of the 4-t-butyl­pyridine and iodide/triiodide system in dye-sensitized solar cells see: Campbell et al. (2004 ▶); Lee et al. (2010 ▶); Wang et al. (2005 ▶). For related structures, see: Fialho et al. (1996 ▶); Kochel (2006 ▶).

Experimental

Crystal data

C9H14N+·I3 −·C9H13N

M = 652.12

Tetragonal,

a = 11.6862 (4) Å

c = 17.1665 (13) Å

V = 2344.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 4.00 mm−1

T = 293 K

0.55 × 0.50 × 0.40 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.217, T max = 0.298

23722 measured reflections

2217 independent reflections

1758 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.04

2217 reflections

119 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.80 e Å−3

Δρmin = −0.77 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001371/sj5091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001371/sj5091Isup2.hkl

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

C9H14N+·I3−·C9H13N	Dx = 1.848 Mg m−3
Mr = 652.12	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42/n	Cell parameters from 9942 reflections
Hall symbol: -P 4bc	θ = 2.4–25.6°
a = 11.6862 (4) Å	µ = 4.00 mm−1
c = 17.1665 (13) Å	T = 293 K
V = 2344.4 (2) Å3	Block, red
Z = 4	0.55 × 0.50 × 0.40 mm
F(000) = 1232

Bruker APEXII CCD area-detector diffractometer	2217 independent reflections
Radiation source: fine-focus sealed tube	1758 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −14→14
Tmin = 0.217, Tmax = 0.298	k = −14→14
23722 measured reflections	l = −20→20

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0303P)2 + 5.5874P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2217 reflections	Δρmax = 0.80 e Å−3
119 parameters	Δρmin = −0.77 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00208 (15)

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	Occ. (<1)
C1	0.0501 (4)	0.9717 (5)	0.3368 (3)	0.0641 (12)
H1	0.0502	1.0414	0.3107	0.077*
C2	0.1482 (4)	0.9081 (6)	0.3407 (3)	0.0749 (15)
H2	0.2140	0.9358	0.3169	0.090*
C3	0.0595 (5)	0.7687 (5)	0.4119 (3)	0.0694 (14)
H3	0.0625	0.6988	0.4376	0.083*
C4	−0.0414 (4)	0.8291 (4)	0.4105 (3)	0.0608 (12)
H4	−0.1055	0.8001	0.4360	0.073*
C5	−0.0485 (4)	0.9329 (4)	0.3715 (2)	0.0505 (10)
C6	−0.1613 (4)	0.9989 (4)	0.3681 (3)	0.0590 (12)
C7	−0.179 (2)	1.059 (2)	0.2943 (13)	0.099 (7)*	0.33
H7A	−0.1554	1.0099	0.2521	0.148*	0.33
H7B	−0.1338	1.1273	0.2937	0.148*	0.33
H7C	−0.2582	1.0775	0.2886	0.148*	0.33
C8	−0.2650 (16)	0.9078 (16)	0.3731 (13)	0.077 (5)*	0.33
H8A	−0.2680	0.8641	0.3258	0.116*	0.33
H8B	−0.3359	0.9479	0.3801	0.116*	0.33
H8C	−0.2526	0.8573	0.4164	0.116*	0.33
C9	−0.1911 (15)	1.0409 (17)	0.4482 (9)	0.051 (4)*	0.33
H9A	−0.1303	1.0882	0.4675	0.076*	0.33
H9B	−0.2017	0.9767	0.4823	0.076*	0.33
H9C	−0.2606	1.0847	0.4459	0.076*	0.33
C7'	−0.144 (2)	1.125 (2)	0.3487 (17)	0.118 (8)*	0.33
H7'1	−0.1136	1.1639	0.3933	0.177*	0.33
H7'2	−0.2159	1.1584	0.3344	0.177*	0.33
H7'3	−0.0912	1.1316	0.3060	0.177*	0.33
C8'	−0.230 (2)	0.953 (2)	0.3061 (13)	0.091 (7)*	0.33
H8'1	−0.3007	0.9947	0.3031	0.136*	0.33
H8'2	−0.2453	0.8739	0.3159	0.136*	0.33
H8'3	−0.1894	0.9609	0.2577	0.136*	0.33
C9'	−0.2236 (18)	0.9924 (19)	0.4480 (12)	0.085 (6)*	0.33
H9'1	−0.1681	0.9934	0.4892	0.127*	0.33
H9'2	−0.2673	0.9230	0.4507	0.127*	0.33
H9'3	−0.2739	1.0569	0.4534	0.127*	0.33
C8"	−0.2550 (14)	0.9235 (14)	0.3301 (12)	0.052 (3)*	0.33
H8"1	−0.3257	0.9653	0.3282	0.078*	0.33
H8"2	−0.2653	0.8553	0.3604	0.078*	0.33
H8"3	−0.2321	0.9033	0.2782	0.078*	0.33
C7"	−0.1486 (14)	1.1071 (15)	0.3079 (11)	0.057 (4)*	0.33
H7"1	−0.0932	1.1602	0.3280	0.085*	0.33
H7"2	−0.2212	1.1449	0.3027	0.085*	0.33
H7"3	−0.1240	1.0798	0.2579	0.085*	0.33
C9"	−0.1668 (19)	1.0791 (19)	0.4363 (13)	0.085 (7)*	0.33
H9"1	−0.0907	1.1022	0.4504	0.127*	0.33
H9"2	−0.2021	1.0410	0.4796	0.127*	0.33
H9"3	−0.2110	1.1452	0.4224	0.127*	0.33
N1	0.1527 (4)	0.8086 (4)	0.3770 (3)	0.0699 (12)
I1	0.2500	0.2500	0.38499 (3)	0.06646 (18)
I2	0.05632 (4)	0.40649 (4)	0.38862 (3)	0.1013 (2)
H99	0.220 (6)	0.772 (11)	0.381 (5)	0.09 (4)*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.060 (3)	0.068 (3)	0.065 (3)	−0.004 (2)	0.000 (2)	0.009 (2)
C2	0.048 (3)	0.102 (4)	0.074 (4)	−0.002 (3)	0.008 (3)	−0.001 (3)
C3	0.067 (3)	0.068 (3)	0.073 (3)	0.013 (3)	−0.004 (3)	0.008 (3)
C4	0.055 (3)	0.059 (3)	0.068 (3)	0.001 (2)	0.007 (2)	0.007 (2)
C5	0.050 (2)	0.055 (3)	0.047 (2)	0.0031 (19)	−0.0037 (19)	−0.0077 (19)
C6	0.057 (3)	0.060 (3)	0.061 (3)	0.014 (2)	−0.006 (2)	−0.010 (2)
N1	0.053 (3)	0.091 (3)	0.066 (3)	0.020 (2)	−0.005 (2)	−0.011 (2)
I1	0.0663 (3)	0.0676 (3)	0.0656 (3)	0.0000 (2)	0.000	0.000
I2	0.0790 (3)	0.1007 (4)	0.1243 (4)	0.0253 (2)	−0.0064 (3)	0.0184 (3)

C1—C2	1.368 (7)	C8—H8C	0.9600
C1—C5	1.375 (6)	C9—H9A	0.9600
C1—H1	0.9300	C9—H9B	0.9600
C2—N1	1.320 (7)	C9—H9C	0.9600
C2—H2	0.9300	C7'—H7'1	0.9600
C3—N1	1.327 (7)	C7'—H7'2	0.9600
C3—C4	1.374 (7)	C7'—H7'3	0.9600
C3—H3	0.9300	C8'—H8'1	0.9600
C4—C5	1.389 (6)	C8'—H8'2	0.9600
C4—H4	0.9300	C8'—H8'3	0.9600
C5—C6	1.528 (6)	C9'—H9'1	0.9600
C6—C8'	1.44 (2)	C9'—H9'2	0.9600
C6—C7	1.46 (2)	C9'—H9'3	0.9600
C6—C9"	1.50 (2)	C8"—H8"1	0.9600
C6—C9	1.500 (16)	C8"—H8"2	0.9600
C6—C7'	1.52 (3)	C8"—H8"3	0.9600
C6—C8"	1.549 (16)	C7"—H7"1	0.9600
C6—C9'	1.55 (2)	C7"—H7"2	0.9600
C6—C8	1.614 (19)	C7"—H7"3	0.9600
C6—C7"	1.641 (17)	C9"—H9"1	0.9600
C7—H7A	0.9600	C9"—H9"2	0.9600
C7—H7B	0.9600	C9"—H9"3	0.9600
C7—H7C	0.9600	N1—H99	0.90 (2)
C8—H8A	0.9600	I1—I2i	2.9105 (4)
C8—H8B	0.9600	I1—I2	2.9105 (4)
C2—C1—C5	120.2 (5)	H7A—C7—H7C	109.5
C2—C1—H1	119.9	H7B—C7—H7C	109.5
C5—C1—H1	119.9	C6—C8—H8A	109.5
N1—C2—C1	122.4 (5)	C6—C8—H8B	109.5
N1—C2—H2	118.8	H8A—C8—H8B	109.5
C1—C2—H2	118.8	C6—C8—H8C	109.5
N1—C3—C4	121.1 (5)	H8A—C8—H8C	109.5
N1—C3—H3	119.4	H8B—C8—H8C	109.5
C4—C3—H3	119.4	C6—C9—H9A	109.5
C3—C4—C5	120.5 (5)	C6—C9—H9B	109.5
C3—C4—H4	119.7	H9A—C9—H9B	109.5
C5—C4—H4	119.7	C6—C9—H9C	109.5
C1—C5—C4	116.5 (4)	H9A—C9—H9C	109.5
C1—C5—C6	122.8 (4)	H9B—C9—H9C	109.5
C4—C5—C6	120.7 (4)	C6—C7'—H7'1	109.5
C8'—C6—C9"	141.9 (13)	C6—C7'—H7'2	109.5
C7—C6—C9"	111.9 (14)	H7'1—C7'—H7'2	109.5
C8'—C6—C9	132.2 (12)	C6—C7'—H7'3	109.5
C7—C6—C9	127.3 (12)	H7'1—C7'—H7'3	109.5
C8'—C6—C7'	105.7 (14)	H7'2—C7'—H7'3	109.5
C9"—C6—C7'	64.7 (14)	C6—C8'—H8'1	109.5
C9—C6—C7'	85.2 (13)	C6—C8'—H8'2	109.5
C8'—C6—C5	108.8 (9)	H8'1—C8'—H8'2	109.5
C7—C6—C5	113.2 (10)	C6—C8'—H8'3	109.5
C9"—C6—C5	108.8 (9)	H8'1—C8'—H8'3	109.5
C9—C6—C5	109.3 (7)	H8'2—C8'—H8'3	109.5
C7'—C6—C5	112.3 (11)	C6—C9'—H9'1	109.5
C7—C6—C8"	78.9 (12)	C6—C9'—H9'2	109.5
C9"—C6—C8"	130.8 (11)	H9'1—C9'—H9'2	109.5
C9—C6—C8"	114.0 (11)	C6—C9'—H9'3	109.5
C7'—C6—C8"	123.5 (13)	H9'1—C9'—H9'3	109.5
C5—C6—C8"	109.8 (6)	H9'2—C9'—H9'3	109.5
C8'—C6—C9'	112.1 (14)	C6—C8"—H8"1	109.5
C7—C6—C9'	136.4 (12)	C6—C8"—H8"2	109.5
C7'—C6—C9'	107.7 (14)	H8"1—C8"—H8"2	109.5
C5—C6—C9'	110.2 (8)	C6—C8"—H8"3	109.5
C8"—C6—C9'	90.7 (11)	H8"1—C8"—H8"3	109.5
C7—C6—C8	104.9 (12)	H8"2—C8"—H8"3	109.5
C9"—C6—C8	109.8 (12)	C6—C7"—H7"1	109.5
C9—C6—C8	89.6 (11)	C6—C7"—H7"2	109.5
C7'—C6—C8	138.5 (13)	H7"1—C7"—H7"2	109.5
C5—C6—C8	108.2 (8)	C6—C7"—H7"3	109.5
C9'—C6—C8	64.5 (11)	H7"1—C7"—H7"3	109.5
C8'—C6—C7"	82.5 (11)	H7"2—C7"—H7"3	109.5
C9"—C6—C7"	90.8 (11)	C6—C9"—H9"1	109.5
C9—C6—C7"	110.2 (10)	C6—C9"—H9"2	109.5
C5—C6—C7"	109.6 (7)	H9"1—C9"—H9"2	109.5
C8"—C6—C7"	103.7 (10)	C6—C9"—H9"3	109.5
C9'—C6—C7"	129.5 (10)	H9"1—C9"—H9"3	109.5
C8—C6—C7"	127.6 (10)	H9"2—C9"—H9"3	109.5
C6—C7—H7A	109.5	C2—N1—C3	119.3 (4)
C6—C7—H7B	109.5	C2—N1—H99	120 (9)
H7A—C7—H7B	109.5	C3—N1—H99	121 (9)
C6—C7—H7C	109.5	I2i—I1—I2	177.55 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H99···N1ii	0.90	1.76	2.655 (7)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H99⋯N1i	0.90	1.76	2.655 (7)	172

Symmetry code: (i) .