4,4'-Di-tert-butyl-2,2'-dipyridinium dichloride.

In the title compound, C(18)H(26)N(2) (2+)·2Cl(-), the complete dication is generated by crystallographic inversion symmetry; both N atoms are protonated and engaged in strong and highly directional N-H⋯Cl hydrogen bonds. Additional weak C-H⋯Cl contacts promote the formation of a tape along ca. [110]. The crystal structure can be described by the parallel packing of these tapes. The crystal studied was a non-merohedral twin with twin law [-1 0 0, 0 -1 0, -0.887 0.179 1] and the final BASF parameter refining to 0.026 (2) .

Related literature

For metallic complexes of 4,4′-di-tert-butyl-2,2′-dipyridyl, see: Momeni et al. (2010 ▶); Li et al. (2005 ▶). For related organic crystals from our research groups, see: Amarante, Figueiredo et al. (2009 ▶); Amarante, Gonçalves & Almeida Paz (2009 ▶); Amarante, Paz et al. (2009 ▶); Batsanov et al. (2007 ▶); Coelho et al. (2007 ▶); Herrmann et al. (1990 ▶); Paz & Klinowski (2003 ▶); Paz et al. (2002 ▶). For graph-set notation, see: Grell et al. (1999 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For the refinement, see: Cooper et al. (2002 ▶).

Experimental

Crystal data

C18H26N2 2+·2Cl−

M = 341.31

Triclinic,

a = 5.9017 (8) Å

b = 6.1949 (8) Å

c = 13.0758 (17) Å

α = 89.633 (8)°

β = 79.049 (7)°

γ = 75.915 (7)°

V = 454.84 (10) Å3

Z = 1

Mo Kα radiation

μ = 0.36 mm−1

T = 150 K

0.12 × 0.03 × 0.03 mm

Data collection

Bruker X8 KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.959, T max = 0.989

14551 measured reflections

2054 independent reflections

1654 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.188

S = 1.25

2054 reflections

107 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025529/bt5558sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025529/bt5558Isup2.hkl

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

C18H26N22+·2Cl−	Z = 1
Mr = 341.31	F(000) = 182
Triclinic, P1	Dx = 1.246 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9017 (8) Å	Cell parameters from 3784 reflections
b = 6.1949 (8) Å	θ = 3.2–28.8°
c = 13.0758 (17) Å	µ = 0.36 mm−1
α = 89.633 (8)°	T = 150 K
β = 79.049 (7)°	Block, colourless
γ = 75.915 (7)°	0.12 × 0.03 × 0.03 mm
V = 454.84 (10) Å3

Bruker X8 KappaCCD APEXII diffractometer	2054 independent reflections
Radiation source: fine-focus sealed tube	1654 reflections with I > 2σ(I)
graphite	Rint = 0.074
ω and φ scans	θmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −7→7
Tmin = 0.959, Tmax = 0.989	k = −8→8
14551 measured reflections	l = −16→16

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.25	w = 1/[σ2(Fo2) + (0.P)2 + 2.3813P] where P = (Fo2 + 2Fc2)/3
2054 reflections	(Δ/σ)max < 0.001
107 parameters	Δρmax = 0.72 e Å−3
1 restraint	Δρmin = −0.39 e Å−3

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
Cl1	−0.5222 (2)	0.2342 (2)	1.16162 (10)	0.0234 (3)
N1	−0.1611 (7)	0.2931 (6)	0.9791 (3)	0.0167 (8)
H1	−0.253 (8)	0.281 (9)	1.046 (2)	0.025*
C1	−0.1874 (8)	0.1531 (8)	0.9071 (4)	0.0189 (10)
H1A	−0.2924	0.0589	0.9262	0.023*
C2	−0.0648 (8)	0.1433 (8)	0.8057 (4)	0.0195 (10)
H2A	−0.0832	0.0419	0.7555	0.023*
C3	0.0868 (8)	0.2843 (7)	0.7777 (4)	0.0164 (9)
C4	0.1157 (8)	0.4233 (8)	0.8556 (4)	0.0196 (10)
H4A	0.2225	0.5166	0.8387	0.024*
C5	−0.0083 (8)	0.4275 (7)	0.9569 (3)	0.0150 (9)
C6	0.2115 (9)	0.3004 (8)	0.6655 (4)	0.0186 (10)
C7	0.1739 (10)	0.1275 (9)	0.5916 (4)	0.0295 (12)
H7A	0.2402	−0.0225	0.6134	0.044*
H7B	0.2543	0.1459	0.5204	0.044*
H7C	0.0031	0.1484	0.5935	0.044*
C8	0.4802 (10)	0.2668 (10)	0.6597 (4)	0.0303 (12)
H8A	0.5076	0.3804	0.7045	0.045*
H8B	0.5581	0.2801	0.5876	0.045*
H8C	0.5466	0.1185	0.6834	0.045*
C9	0.1040 (12)	0.5355 (9)	0.6314 (4)	0.0358 (14)
H9A	−0.0690	0.5593	0.6396	0.054*
H9B	0.1730	0.5500	0.5581	0.054*
H9C	0.1396	0.6468	0.6746	0.054*

	U11	U22	U33	U12	U13	U23
Cl1	0.0211 (6)	0.0222 (6)	0.0284 (6)	−0.0127 (4)	0.0011 (5)	−0.0006 (4)
N1	0.0168 (19)	0.0172 (18)	0.020 (2)	−0.0089 (15)	−0.0062 (15)	0.0031 (15)
C1	0.018 (2)	0.016 (2)	0.027 (2)	−0.0082 (18)	−0.0080 (19)	0.0013 (18)
C2	0.019 (2)	0.014 (2)	0.026 (3)	−0.0034 (18)	−0.0075 (19)	−0.0018 (18)
C3	0.014 (2)	0.014 (2)	0.020 (2)	−0.0001 (17)	−0.0051 (18)	−0.0012 (17)
C4	0.016 (2)	0.022 (2)	0.024 (2)	−0.0095 (19)	−0.0028 (19)	0.0025 (19)
C5	0.012 (2)	0.015 (2)	0.021 (2)	−0.0048 (17)	−0.0073 (17)	0.0014 (18)
C6	0.023 (2)	0.017 (2)	0.017 (2)	−0.0079 (19)	−0.0023 (19)	0.0010 (17)
C7	0.034 (3)	0.032 (3)	0.021 (3)	−0.012 (2)	0.002 (2)	−0.009 (2)
C8	0.023 (3)	0.040 (3)	0.028 (3)	−0.013 (2)	0.000 (2)	−0.002 (2)
C9	0.052 (4)	0.025 (3)	0.022 (3)	0.001 (3)	−0.001 (3)	0.005 (2)

N1—C1	1.340 (6)	C6—C7	1.530 (7)
N1—C5	1.361 (5)	C6—C8	1.536 (7)
N1—H1	0.952 (10)	C6—C9	1.541 (7)
C1—C2	1.378 (7)	C7—H7A	0.9800
C1—H1A	0.9500	C7—H7B	0.9800
C2—C3	1.396 (6)	C7—H7C	0.9800
C2—H2A	0.9500	C8—H8A	0.9800
C3—C4	1.399 (6)	C8—H8B	0.9800
C3—C6	1.526 (6)	C8—H8C	0.9800
C4—C5	1.383 (6)	C9—H9A	0.9800
C4—H4A	0.9500	C9—H9B	0.9800
C5—C5i	1.478 (9)	C9—H9C	0.9800
C1—N1—C5	122.0 (4)	C3—C6—C9	106.8 (4)
C1—N1—H1	113 (3)	C7—C6—C9	109.1 (4)
C5—N1—H1	125 (3)	C8—C6—C9	109.9 (4)
N1—C1—C2	121.2 (4)	C6—C7—H7A	109.5
N1—C1—H1A	119.4	C6—C7—H7B	109.5
C2—C1—H1A	119.4	H7A—C7—H7B	109.5
C1—C2—C3	119.1 (4)	C6—C7—H7C	109.5
C1—C2—H2A	120.4	H7A—C7—H7C	109.5
C3—C2—H2A	120.4	H7B—C7—H7C	109.5
C2—C3—C4	118.1 (4)	C6—C8—H8A	109.5
C2—C3—C6	122.7 (4)	C6—C8—H8B	109.5
C4—C3—C6	119.1 (4)	H8A—C8—H8B	109.5
C5—C4—C3	121.2 (4)	C6—C8—H8C	109.5
C5—C4—H4A	119.4	H8A—C8—H8C	109.5
C3—C4—H4A	119.4	H8B—C8—H8C	109.5
N1—C5—C4	118.3 (4)	C6—C9—H9A	109.5
N1—C5—C5i	117.1 (5)	C6—C9—H9B	109.5
C4—C5—C5i	124.6 (5)	H9A—C9—H9B	109.5
C3—C6—C7	112.4 (4)	C6—C9—H9C	109.5
C3—C6—C8	110.2 (4)	H9A—C9—H9C	109.5
C7—C6—C8	108.5 (4)	H9B—C9—H9C	109.5
C5—N1—C1—C2	−1.8 (7)	C3—C4—C5—N1	−0.3 (7)
N1—C1—C2—C3	−0.9 (7)	C3—C4—C5—C5i	−178.7 (5)
C1—C2—C3—C4	2.8 (7)	C2—C3—C6—C7	−6.6 (6)
C1—C2—C3—C6	−174.2 (4)	C4—C3—C6—C7	176.5 (4)
C2—C3—C4—C5	−2.2 (7)	C2—C3—C6—C8	−127.7 (5)
C6—C3—C4—C5	174.9 (4)	C4—C3—C6—C8	55.4 (6)
C1—N1—C5—C4	2.4 (6)	C2—C3—C6—C9	113.0 (5)
C1—N1—C5—C5i	−179.1 (5)	C4—C3—C6—C9	−64.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.95 (1)	2.05 (2)	2.967 (4)	162 (5)
C1—H1A···Cl1ii	0.95	2.70	3.479 (3)	140
C4—H4A···Cl1i	0.95	2.61	3.543 (9)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.95 (1)	2.05 (2)	2.967 (4)	162 (5)
C1—H1A⋯Cl1i	0.95	2.70	3.479 (3)	140
C4—H4A⋯Cl1ii	0.95	2.61	3.543 (9)	166

Symmetry codes: (i) ; (ii) .