Bis(pyridin-2-ylmeth-yl)ammonium nitrate.

In the title compound, C12H14N3 (+)·NO3 (-), the mononitrate of protonated bis-(pyridin-2-ylmeth-yl)amine, the least-squares planes defined by the non-H atoms of the two aromatic moieties inter-sect at an angle of 7.91 (6)°. In the crystal, N-H⋯N, N-H⋯O and C-H⋯N hydrogen bonds, as well as C-H⋯O contacts, connect the entities into a three-dimensional network. The shortest centroid-centroid distance between two aromatic systems is 3.7255 (8) Å and is apparent between the two different aromatic moieties.

Related literature

For the crystal structure of the trinitrate of bis­(pyridin-2-ylmeth­yl)amine, see: Junk et al. (2006 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H14N3 +·NO3 −

M = 262.27

Orthorhombic,

a = 11.2236 (2) Å

b = 13.4714 (4) Å

c = 16.5303 (4) Å

V = 2499.34 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.50 × 0.35 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.923, T max = 1.000

12816 measured reflections

3082 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.122

S = 1.04

3082 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008593/vn2068sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008593/vn2068Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008593/vn2068Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008593/vn2068Isup4.cml

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

C12H14N3+·NO3−	F(000) = 1104
Mr = 262.27	Dx = 1.394 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5628 reflections
a = 11.2236 (2) Å	θ = 2.5–28.2°
b = 13.4714 (4) Å	µ = 0.10 mm−1
c = 16.5303 (4) Å	T = 200 K
V = 2499.34 (11) Å3	Irregular, white
Z = 8	0.50 × 0.35 × 0.24 mm

Bruker APEXII CCD diffractometer	3082 independent reflections
Radiation source: fine-focus sealed tube	2568 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→14
Tmin = 0.923, Tmax = 1.000	k = −17→17
12816 measured reflections	l = −22→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0695P)2 + 0.627P] where P = (Fo2 + 2Fc2)/3
3082 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.53822 (10)	0.03915 (9)	0.09542 (8)	0.0595 (3)
O2	0.72195 (8)	0.07826 (8)	0.08342 (6)	0.0438 (3)
O3	0.58787 (10)	0.19315 (8)	0.09035 (8)	0.0540 (3)
N1	0.76754 (9)	0.13548 (8)	0.57810 (6)	0.0257 (2)
H71	0.6936 (16)	0.1564 (13)	0.5883 (10)	0.044 (4)*
H72	0.7725 (15)	0.0688 (14)	0.5820 (10)	0.044 (4)*
N2	0.61491 (9)	0.10403 (8)	0.08911 (6)	0.0300 (2)
N11	0.59551 (10)	0.11038 (8)	0.46858 (6)	0.0345 (2)
N21	0.71063 (9)	0.11508 (7)	0.73540 (6)	0.0297 (2)
C1	0.79740 (12)	0.16440 (10)	0.49410 (7)	0.0351 (3)
H1A	0.8717	0.1305	0.4774	0.042*
H1B	0.8116	0.2369	0.4919	0.042*
C2	0.84972 (10)	0.18126 (9)	0.63756 (7)	0.0295 (2)
H2A	0.8442	0.2544	0.6335	0.035*
H2B	0.9326	0.1617	0.6246	0.035*
C11	0.69911 (12)	0.13770 (8)	0.43630 (7)	0.0313 (3)
C12	0.71806 (18)	0.14422 (10)	0.35348 (8)	0.0507 (4)
H12	0.7937	0.1623	0.3324	0.061*
C13	0.6227 (2)	0.12345 (11)	0.30224 (9)	0.0657 (6)
H13	0.6315	0.1291	0.2453	0.079*
C14	0.51552 (19)	0.09468 (12)	0.33522 (11)	0.0598 (5)
H14	0.4496	0.0794	0.3014	0.072*
C15	0.50553 (14)	0.08849 (11)	0.41766 (10)	0.0472 (4)
H15	0.4316	0.0678	0.4400	0.057*
C21	0.82056 (10)	0.14965 (8)	0.72268 (7)	0.0255 (2)
C22	0.90516 (11)	0.16031 (9)	0.78369 (7)	0.0309 (3)
H22	0.9828	0.1843	0.7719	0.037*
C23	0.87333 (12)	0.13503 (9)	0.86208 (7)	0.0359 (3)
H23	0.9287	0.1417	0.9052	0.043*
C24	0.75986 (13)	0.10001 (9)	0.87633 (7)	0.0366 (3)
H24	0.7353	0.0829	0.9295	0.044*
C25	0.68233 (11)	0.09025 (9)	0.81153 (7)	0.0346 (3)
H25	0.6049	0.0646	0.8216	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0397 (6)	0.0467 (6)	0.0920 (9)	−0.0119 (5)	−0.0001 (5)	0.0126 (6)
O2	0.0298 (5)	0.0473 (6)	0.0542 (6)	0.0045 (4)	0.0046 (4)	−0.0013 (4)
O3	0.0484 (6)	0.0330 (5)	0.0805 (8)	0.0060 (4)	−0.0001 (5)	0.0027 (5)
N1	0.0254 (5)	0.0290 (5)	0.0229 (4)	−0.0029 (4)	−0.0008 (3)	0.0030 (3)
N2	0.0309 (5)	0.0333 (5)	0.0260 (5)	0.0003 (4)	0.0013 (4)	0.0017 (4)
N11	0.0339 (5)	0.0374 (5)	0.0322 (5)	0.0069 (4)	−0.0073 (4)	−0.0051 (4)
N21	0.0281 (5)	0.0325 (5)	0.0284 (5)	−0.0005 (4)	0.0000 (4)	0.0034 (4)
C1	0.0395 (6)	0.0421 (6)	0.0236 (5)	−0.0092 (5)	0.0062 (5)	0.0033 (5)
C2	0.0270 (5)	0.0327 (6)	0.0287 (6)	−0.0068 (4)	−0.0022 (4)	0.0014 (4)
C11	0.0494 (7)	0.0219 (5)	0.0225 (5)	0.0018 (5)	−0.0017 (5)	0.0013 (4)
C12	0.0989 (13)	0.0300 (6)	0.0233 (6)	−0.0127 (7)	0.0039 (7)	0.0010 (5)
C13	0.138 (2)	0.0328 (7)	0.0259 (7)	0.0027 (9)	−0.0235 (9)	−0.0003 (5)
C14	0.0905 (14)	0.0376 (7)	0.0513 (9)	0.0206 (8)	−0.0415 (9)	−0.0113 (7)
C15	0.0444 (8)	0.0432 (7)	0.0542 (9)	0.0160 (6)	−0.0214 (6)	−0.0127 (6)
C21	0.0259 (5)	0.0244 (5)	0.0263 (5)	0.0028 (4)	−0.0025 (4)	−0.0014 (4)
C22	0.0289 (5)	0.0323 (6)	0.0316 (6)	0.0044 (4)	−0.0048 (4)	−0.0051 (4)
C23	0.0464 (7)	0.0334 (6)	0.0278 (6)	0.0122 (5)	−0.0096 (5)	−0.0052 (5)
C24	0.0546 (8)	0.0303 (6)	0.0248 (5)	0.0119 (5)	0.0031 (5)	0.0020 (4)
C25	0.0367 (7)	0.0339 (6)	0.0332 (6)	0.0018 (5)	0.0063 (5)	0.0047 (5)

O1—N2	1.2311 (15)	C11—C12	1.3883 (17)
O2—N2	1.2541 (14)	C12—C13	1.393 (3)
O3—N2	1.2385 (14)	C12—H12	0.9500
N1—C1	1.4806 (14)	C13—C14	1.376 (3)
N1—C2	1.4822 (14)	C13—H13	0.9500
N1—H71	0.893 (18)	C14—C15	1.370 (2)
N1—H72	0.902 (19)	C14—H14	0.9500
N11—C11	1.3313 (17)	C15—H15	0.9500
N11—C15	1.3473 (17)	C21—C22	1.3926 (15)
N21—C21	1.3354 (15)	C22—C23	1.3866 (18)
N21—C25	1.3403 (15)	C22—H22	0.9500
C1—C11	1.5030 (18)	C23—C24	1.378 (2)
C1—H1A	0.9900	C23—H23	0.9500
C1—H1B	0.9900	C24—C25	1.3864 (19)
C2—C21	1.5061 (16)	C24—H24	0.9500
C2—H2A	0.9900	C25—H25	0.9500
C2—H2B	0.9900
C1—N1—C2	111.81 (9)	C11—C12—H12	121.0
C1—N1—H71	107.7 (11)	C13—C12—H12	121.0
C2—N1—H71	108.8 (11)	C14—C13—C12	119.15 (15)
C1—N1—H72	108.4 (10)	C14—C13—H13	120.4
C2—N1—H72	109.1 (10)	C12—C13—H13	120.4
H71—N1—H72	111.0 (15)	C15—C14—C13	118.86 (15)
O1—N2—O3	121.03 (11)	C15—C14—H14	120.6
O1—N2—O2	118.66 (11)	C13—C14—H14	120.6
O3—N2—O2	120.29 (11)	N11—C15—C14	123.15 (17)
C11—N11—C15	117.70 (13)	N11—C15—H15	118.4
C21—N21—C25	116.99 (10)	C14—C15—H15	118.4
N1—C1—C11	111.53 (10)	N21—C21—C22	123.50 (11)
N1—C1—H1A	109.3	N21—C21—C2	116.51 (10)
C11—C1—H1A	109.3	C22—C21—C2	119.95 (10)
N1—C1—H1B	109.3	C23—C22—C21	118.41 (12)
C11—C1—H1B	109.3	C23—C22—H22	120.8
H1A—C1—H1B	108.0	C21—C22—H22	120.8
N1—C2—C21	111.51 (9)	C24—C23—C22	118.81 (11)
N1—C2—H2A	109.3	C24—C23—H23	120.6
C21—C2—H2A	109.3	C22—C23—H23	120.6
N1—C2—H2B	109.3	C23—C24—C25	118.70 (11)
C21—C2—H2B	109.3	C23—C24—H24	120.6
H2A—C2—H2B	108.0	C25—C24—H24	120.6
N11—C11—C12	123.13 (13)	N21—C25—C24	123.58 (12)
N11—C11—C1	116.90 (10)	N21—C25—H25	118.2
C12—C11—C1	119.95 (13)	C24—C25—H25	118.2
C11—C12—C13	117.98 (17)
C2—N1—C1—C11	−166.97 (10)	C13—C14—C15—N11	0.8 (2)
C1—N1—C2—C21	−178.69 (10)	C25—N21—C21—C22	0.28 (17)
C15—N11—C11—C12	−0.18 (18)	C25—N21—C21—C2	−177.56 (10)
C15—N11—C11—C1	178.44 (11)	N1—C2—C21—N21	−20.60 (14)
N1—C1—C11—N11	11.67 (16)	N1—C2—C21—C22	161.48 (10)
N1—C1—C11—C12	−169.68 (11)	N21—C21—C22—C23	−0.91 (17)
N11—C11—C12—C13	1.7 (2)	C2—C21—C22—C23	176.87 (10)
C1—C11—C12—C13	−176.91 (12)	C21—C22—C23—C24	0.33 (17)
C11—C12—C13—C14	−1.9 (2)	C22—C23—C24—C25	0.79 (17)
C12—C13—C14—C15	0.8 (2)	C21—N21—C25—C24	0.94 (18)
C11—N11—C15—C14	−1.1 (2)	C23—C24—C25—N21	−1.49 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2	0.95	2.61	3.5339 (18)	164
N1—H71···O3i	0.893 (18)	2.349 (18)	3.0721 (15)	138.2 (14)
N1—H72···O2ii	0.902 (19)	1.982 (19)	2.8831 (15)	176.1 (15)
N1—H72···O1ii	0.902 (19)	2.584 (18)	3.2201 (16)	128.1 (14)
N1—H72···N2ii	0.902 (19)	2.651 (18)	3.4905 (15)	155.1 (14)
C15—H15···O2iii	0.95	2.39	3.1858 (19)	141
C1—H1A···O1iv	0.99	2.54	3.5132 (18)	167
C25—H25···O1v	0.95	2.53	3.3959 (16)	151
C24—H24···O2vi	0.95	2.55	3.4620 (16)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N2	0.95	2.61	3.5339 (18)	164
N1—H71⋯O3i	0.893 (18)	2.349 (18)	3.0721 (15)	138.2 (14)
N1—H72⋯O2ii	0.902 (19)	1.982 (19)	2.8831 (15)	176.1 (15)
N1—H72⋯O1ii	0.902 (19)	2.584 (18)	3.2201 (16)	128.1 (14)
N1—H72⋯N2ii	0.902 (19)	2.651 (18)	3.4905 (15)	155.1 (14)
C15—H15⋯O2iii	0.95	2.39	3.1858 (19)	141
C1—H1A⋯O1iv	0.99	2.54	3.5132 (18)	167
C25—H25⋯O1v	0.95	2.53	3.3959 (16)	151
C24—H24⋯O2vi	0.95	2.55	3.4620 (16)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .