4-tert-Butyl-2-(4-tert-butyl-pyridin-2-yl)pyridinium nitrate.

In the title compound, C(18)H(25)N(2) (+)·NO(3) (-), the dihedral angle between the pyridine rings is 19.06 (10)°. In the crystal, the ions are linked into a three-dimensional network by N-H⋯O and C-H⋯O hydrogen-bonding inter-actions.

Related literature

For background to the coordination chemistry and applications of bipyridine and its derivatives, see: Duan et al. (2010 ▶); Morrow & Trogler (1989 ▶); Noro et al. (2000 ▶); Yaghi et al. (1998 ▶); Huertas et al. (2001 ▶); Qin et al. (2002 ▶).

Experimental

Crystal data

C18H25N2 +·NO3 −

M = 331.41

Orthorhombic,

a = 11.606 (5) Å

b = 9.770 (4) Å

c = 16.199 (7) Å

V = 1836.8 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 273 K

0.29 × 0.24 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.962, T max = 0.978

11773 measured reflections

1705 independent reflections

1314 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.112

S = 1.06

1705 reflections

227 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028030/rz2623sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028030/rz2623Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028030/rz2623Isup3.cml

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

C18H25N2+·NO3−	F(000) = 712.0
Mr = 331.41	Dx = 1.198 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1686 reflections
a = 11.606 (5) Å	θ = 2.4–25.1°
b = 9.770 (4) Å	µ = 0.08 mm−1
c = 16.199 (7) Å	T = 273 K
V = 1836.8 (13) Å3	Block, colourless
Z = 4	0.29 × 0.24 × 0.19 mm

Bruker SMART CCD area-detector diffractometer	1705 independent reflections
Radiation source: fine-focus sealed tube	1314 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 25.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.962, Tmax = 0.978	k = −11→11
11773 measured reflections	l = −18→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.064P)2 + 0.0558P] where P = (Fo2 + 2Fc2)/3
1705 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.13 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
O1	0.6857 (3)	0.6853 (3)	1.06496 (18)	0.0996 (11)
O3	0.6436 (2)	0.5517 (3)	0.96612 (17)	0.0845 (9)
O2	0.7322 (3)	0.7406 (4)	0.9424 (2)	0.1063 (11)
N1	0.2126 (2)	0.0984 (3)	0.64095 (16)	0.0490 (7)
H1N	0.280 (3)	0.143 (3)	0.613 (2)	0.059 (9)*
N2	0.4248 (2)	0.1079 (3)	0.70159 (18)	0.0570 (8)
N3	0.6866 (2)	0.6606 (3)	0.9902 (2)	0.0628 (8)
C1	0.4700 (3)	0.1084 (3)	0.8731 (2)	0.0484 (8)
C2	0.5555 (3)	0.1325 (4)	0.8155 (2)	0.0626 (10)
H2	0.6306	0.1493	0.8327	0.075*
C3	0.5294 (3)	0.1316 (5)	0.7323 (3)	0.0669 (10)
H3	0.5888	0.1486	0.6952	0.080*
C4	0.3599 (3)	0.0832 (3)	0.8416 (2)	0.0455 (7)
H4	0.2988	0.0660	0.8773	0.055*
C5	0.3418 (3)	0.0838 (3)	0.7571 (2)	0.0438 (7)
C6	0.2263 (3)	0.0558 (3)	0.71989 (17)	0.0424 (7)
C7	0.1355 (2)	−0.0087 (3)	0.7586 (2)	0.0438 (7)
H7	0.1440	−0.0385	0.8128	0.053*
C8	0.1142 (3)	0.0787 (4)	0.5994 (2)	0.0569 (9)
H8	0.1078	0.1091	0.5452	0.068*
C9	0.0233 (3)	0.0144 (3)	0.6360 (2)	0.0530 (8)
H9	−0.0443	0.0001	0.6064	0.064*
C10	0.0312 (3)	−0.0301 (3)	0.71786 (19)	0.0458 (8)
C11	0.4935 (3)	0.1032 (4)	0.9658 (2)	0.0592 (9)
C12	0.6147 (4)	0.1546 (7)	0.9880 (3)	0.119 (2)
H12A	0.6713	0.0967	0.9625	0.178*
H12B	0.6245	0.1524	1.0468	0.178*
H12C	0.6241	0.2467	0.9685	0.178*
C13	0.4872 (5)	−0.0481 (5)	0.9912 (3)	0.1001 (15)
H13A	0.4117	−0.0831	0.9794	0.150*
H13B	0.5025	−0.0562	1.0492	0.150*
H13C	0.5436	−0.0994	0.9608	0.150*
C14	0.4034 (5)	0.1836 (6)	1.0136 (3)	0.1090 (18)
H14A	0.4091	0.2788	0.9996	0.163*
H14B	0.4163	0.1721	1.0717	0.163*
H14C	0.3280	0.1505	0.9996	0.163*
C15	−0.0693 (3)	−0.0977 (3)	0.7623 (2)	0.0533 (8)
C16	−0.0320 (4)	−0.2367 (4)	0.7949 (3)	0.0861 (13)
H16A	−0.0095	−0.2941	0.7496	0.129*
H16B	−0.0950	−0.2785	0.8239	0.129*
H16C	0.0319	−0.2254	0.8318	0.129*
C17	−0.1034 (4)	−0.0060 (4)	0.8356 (3)	0.0831 (13)
H17A	−0.0393	0.0027	0.8727	0.125*
H17B	−0.1674	−0.0463	0.8643	0.125*
H17C	−0.1249	0.0829	0.8156	0.125*
C18	−0.1747 (4)	−0.1165 (6)	0.7074 (4)	0.1001 (17)
H18A	−0.1979	−0.0294	0.6855	0.150*
H18B	−0.2366	−0.1547	0.7392	0.150*
H18C	−0.1561	−0.1772	0.6627	0.150*

	U11	U22	U33	U12	U13	U23
O1	0.136 (3)	0.107 (2)	0.0558 (18)	−0.0491 (19)	0.0177 (17)	−0.0289 (16)
O3	0.097 (2)	0.094 (2)	0.0625 (18)	−0.0245 (17)	0.0054 (16)	−0.0279 (16)
O2	0.092 (2)	0.118 (2)	0.109 (3)	−0.0007 (19)	0.033 (2)	0.042 (2)
N1	0.0528 (17)	0.0565 (16)	0.0379 (15)	−0.0017 (12)	0.0009 (13)	0.0075 (12)
N2	0.0457 (16)	0.075 (2)	0.0502 (17)	−0.0018 (14)	0.0053 (14)	0.0172 (14)
N3	0.0545 (17)	0.074 (2)	0.060 (2)	0.0000 (15)	0.0104 (15)	−0.0011 (18)
C1	0.048 (2)	0.0409 (17)	0.056 (2)	−0.0002 (13)	−0.0028 (16)	0.0012 (14)
C2	0.046 (2)	0.071 (2)	0.071 (3)	−0.0058 (16)	−0.0048 (19)	0.0067 (18)
C3	0.052 (2)	0.085 (3)	0.064 (3)	−0.0027 (18)	0.0098 (19)	0.0224 (19)
C4	0.0428 (17)	0.0480 (17)	0.0458 (19)	−0.0006 (13)	0.0009 (14)	0.0000 (13)
C5	0.0462 (17)	0.0414 (16)	0.0437 (18)	0.0007 (12)	0.0028 (14)	0.0045 (13)
C6	0.0483 (18)	0.0458 (15)	0.0332 (17)	0.0039 (13)	0.0003 (13)	0.0019 (13)
C7	0.0480 (17)	0.0488 (16)	0.0344 (15)	−0.0007 (14)	−0.0008 (15)	0.0043 (13)
C8	0.071 (2)	0.062 (2)	0.0369 (18)	0.0006 (18)	−0.0048 (17)	0.0062 (15)
C9	0.0532 (19)	0.0607 (19)	0.0450 (18)	−0.0029 (15)	−0.0106 (16)	0.0019 (16)
C10	0.0502 (19)	0.0437 (17)	0.0434 (19)	0.0016 (13)	−0.0011 (14)	−0.0014 (14)
C11	0.056 (2)	0.067 (2)	0.055 (2)	0.0018 (16)	−0.0107 (17)	−0.0088 (18)
C12	0.086 (3)	0.193 (6)	0.077 (3)	−0.036 (4)	−0.022 (3)	−0.022 (4)
C13	0.131 (4)	0.106 (4)	0.063 (3)	0.003 (3)	−0.032 (3)	0.015 (3)
C14	0.112 (4)	0.147 (5)	0.068 (3)	0.044 (3)	−0.019 (3)	−0.039 (3)
C15	0.0503 (19)	0.058 (2)	0.052 (2)	−0.0104 (15)	0.0007 (17)	0.0003 (16)
C16	0.089 (3)	0.061 (2)	0.109 (3)	−0.014 (2)	0.012 (3)	0.017 (2)
C17	0.072 (3)	0.084 (3)	0.093 (3)	−0.014 (2)	0.025 (2)	−0.011 (2)
C18	0.072 (3)	0.140 (5)	0.088 (3)	−0.037 (3)	−0.014 (3)	0.006 (3)

O1—N3	1.235 (4)	C11—C14	1.520 (6)
O3—N3	1.239 (4)	C11—C13	1.536 (6)
O2—N3	1.221 (4)	C11—C12	1.536 (6)
N1—C8	1.340 (4)	C12—H12A	0.9600
N1—C6	1.354 (4)	C12—H12B	0.9600
N1—H1N	1.00 (4)	C12—H12C	0.9600
N2—C3	1.332 (5)	C13—H13A	0.9600
N2—C5	1.339 (4)	C13—H13B	0.9600
C1—C2	1.383 (5)	C13—H13C	0.9600
C1—C4	1.398 (4)	C14—H14A	0.9600
C1—C11	1.527 (5)	C14—H14B	0.9600
C2—C3	1.382 (6)	C14—H14C	0.9600
C2—H2	0.9300	C15—C16	1.519 (5)
C3—H3	0.9300	C15—C18	1.524 (5)
C4—C5	1.384 (5)	C15—C17	1.540 (6)
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.495 (4)	C16—H16B	0.9600
C6—C7	1.378 (4)	C16—H16C	0.9600
C7—C10	1.395 (4)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—C9	1.364 (5)	C17—H17C	0.9600
C8—H8	0.9300	C18—H18A	0.9600
C9—C10	1.398 (4)	C18—H18B	0.9600
C9—H9	0.9300	C18—H18C	0.9600
C10—C15	1.521 (5)
C8—N1—C6	122.0 (3)	C11—C12—H12A	109.5
C8—N1—H1N	119 (2)	C11—C12—H12B	109.5
C6—N1—H1N	118 (2)	H12A—C12—H12B	109.5
C3—N2—C5	115.8 (3)	C11—C12—H12C	109.5
O2—N3—O1	120.1 (4)	H12A—C12—H12C	109.5
O2—N3—O3	121.6 (4)	H12B—C12—H12C	109.5
O1—N3—O3	118.3 (3)	C11—C13—H13A	109.5
C2—C1—C4	116.1 (3)	C11—C13—H13B	109.5
C2—C1—C11	122.8 (3)	H13A—C13—H13B	109.5
C4—C1—C11	121.1 (3)	C11—C13—H13C	109.5
C3—C2—C1	120.0 (3)	H13A—C13—H13C	109.5
C3—C2—H2	120.0	H13B—C13—H13C	109.5
C1—C2—H2	120.0	C11—C14—H14A	109.5
N2—C3—C2	124.4 (3)	C11—C14—H14B	109.5
N2—C3—H3	117.8	H14A—C14—H14B	109.5
C2—C3—H3	117.8	C11—C14—H14C	109.5
C5—C4—C1	119.9 (3)	H14A—C14—H14C	109.5
C5—C4—H4	120.0	H14B—C14—H14C	109.5
C1—C4—H4	120.0	C16—C15—C10	109.6 (3)
N2—C5—C4	123.7 (3)	C16—C15—C18	108.9 (3)
N2—C5—C6	114.0 (3)	C10—C15—C18	113.0 (3)
C4—C5—C6	122.3 (3)	C16—C15—C17	109.0 (4)
N1—C6—C7	118.7 (3)	C10—C15—C17	108.0 (3)
N1—C6—C5	115.5 (3)	C18—C15—C17	108.3 (3)
C7—C6—C5	125.9 (3)	C15—C16—H16A	109.5
C6—C7—C10	121.1 (3)	C15—C16—H16B	109.5
C6—C7—H7	119.4	H16A—C16—H16B	109.5
C10—C7—H7	119.4	C15—C16—H16C	109.5
N1—C8—C9	120.5 (3)	H16A—C16—H16C	109.5
N1—C8—H8	119.8	H16B—C16—H16C	109.5
C9—C8—H8	119.8	C15—C17—H17A	109.5
C8—C9—C10	120.3 (3)	C15—C17—H17B	109.5
C8—C9—H9	119.8	H17A—C17—H17B	109.5
C10—C9—H9	119.8	C15—C17—H17C	109.5
C7—C10—C9	117.3 (3)	H17A—C17—H17C	109.5
C7—C10—C15	120.4 (3)	H17B—C17—H17C	109.5
C9—C10—C15	122.3 (3)	C15—C18—H18A	109.5
C14—C11—C1	111.2 (3)	C15—C18—H18B	109.5
C14—C11—C13	109.1 (4)	H18A—C18—H18B	109.5
C1—C11—C13	106.7 (3)	C15—C18—H18C	109.5
C14—C11—C12	110.0 (4)	H18A—C18—H18C	109.5
C1—C11—C12	112.5 (3)	H18B—C18—H18C	109.5
C13—C11—C12	107.2 (4)
C4—C1—C2—C3	0.4 (5)	C6—N1—C8—C9	0.2 (5)
C11—C1—C2—C3	177.9 (4)	N1—C8—C9—C10	0.9 (5)
C5—N2—C3—C2	−0.1 (6)	C6—C7—C10—C9	1.1 (4)
C1—C2—C3—N2	−0.3 (7)	C6—C7—C10—C15	−178.2 (3)
C2—C1—C4—C5	−0.2 (4)	C8—C9—C10—C7	−1.5 (5)
C11—C1—C4—C5	−177.7 (3)	C8—C9—C10—C15	177.8 (3)
C3—N2—C5—C4	0.3 (5)	C2—C1—C11—C14	135.0 (4)
C3—N2—C5—C6	−179.1 (3)	C4—C1—C11—C14	−47.6 (5)
C1—C4—C5—N2	−0.2 (5)	C2—C1—C11—C13	−106.1 (4)
C1—C4—C5—C6	179.2 (3)	C4—C1—C11—C13	71.3 (4)
C8—N1—C6—C7	−0.6 (4)	C2—C1—C11—C12	11.1 (5)
C8—N1—C6—C5	179.2 (3)	C4—C1—C11—C12	−171.5 (4)
N2—C5—C6—N1	−19.3 (4)	C7—C10—C15—C16	−56.6 (4)
C4—C5—C6—N1	161.3 (3)	C9—C10—C15—C16	124.1 (4)
N2—C5—C6—C7	160.5 (3)	C7—C10—C15—C18	−178.2 (3)
C4—C5—C6—C7	−19.0 (5)	C9—C10—C15—C18	2.5 (5)
N1—C6—C7—C10	−0.1 (4)	C7—C10—C15—C17	62.0 (4)
C5—C6—C7—C10	−179.8 (3)	C9—C10—C15—C17	−117.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	1.00 (3)	1.89 (3)	2.716 (4)	137 (3)
C4—H4···O3ii	0.93	2.58	3.480 (4)	164
C7—H7···O3ii	0.93	2.49	3.389 (4)	163
C9—H9···O3iii	0.93	2.60	3.385 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	1.00 (3)	1.89 (3)	2.716 (4)	137 (3)
C4—H4⋯O3ii	0.93	2.58	3.480 (4)	164
C7—H7⋯O3ii	0.93	2.49	3.389 (4)	163
C9—H9⋯O3iii	0.93	2.60	3.385 (4)	143

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