2-Amino-6-(quinoline-2-carboxamido)-pyridinium nitrate.

In the title salt, C(15)H(13)N(4)O(+)·NO(3) (-), an extensive network of N-H⋯N, N-H⋯O and C-H⋯O hydrogen-bond inter-actions are observed throughout the structure. Further stabilization is obtained by π-π stacking inter-actions between inversion-related quinoline systems and inversion-related pyridine rings, with respective centroid-centroid distances of 3.5866 (6) and 3.3980 (6) Å.

Related literature

For related radiopharmaceutical structures, see: Al-Dajani et al. (2010 ▶); Jain et al. (2004 ▶); Van der Berg et al. (2011 ▶).

Experimental

Crystal data

C15H13N4O+·NO3 −

M = 327.30

Monoclinic,

a = 8.183 (2) Å

b = 11.768 (3) Å

c = 14.979 (4) Å

β = 98.37 (1)°

V = 1427.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.49 × 0.41 × 0.31 mm

Data collection

Bruker X8 APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.990, T max = 0.994

26710 measured reflections

3555 independent reflections

3180 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.1

S = 1.04

3555 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036562/pk2439sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036562/pk2439Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036562/pk2439Isup3.cml

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

C15H13N4O+·NO3−	F(000) = 680
Mr = 327.30	Dx = 1.523 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9936 reflections
a = 8.183 (2) Å	θ = 2.2–28.3°
b = 11.768 (3) Å	µ = 0.12 mm−1
c = 14.979 (4) Å	T = 100 K
β = 98.37 (1)°	Cuboid, yellow
V = 1427.1 (6) Å3	0.49 × 0.41 × 0.31 mm
Z = 4

Bruker X8 APEXII KappaCCD diffractometer	3555 independent reflections
Radiation source: sealed tube	3180 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.990, Tmax = 0.994	k = −15→15
26710 measured reflections	l = −19→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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.1	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.6672P] where P = (Fo2 + 2Fc2)/3
3555 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The intensity data were collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 30 s/frame. A total of 1759 frames were collected with a frame width of 0.5° covering up to θ = 28.28° with 100.00% completeness accomplished.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C5	0.44014 (13)	0.29849 (9)	1.00107 (7)	0.0136 (2)
C4	0.36313 (14)	0.35271 (9)	0.92503 (7)	0.0165 (2)
H4	0.3674	0.323	0.8679	0.02*
C3	0.27835 (14)	0.45365 (10)	0.93606 (8)	0.0190 (2)
H3	0.2243	0.4909	0.8854	0.023*
C2	0.27319 (14)	0.49912 (10)	1.02018 (8)	0.0191 (2)
H2	0.2165	0.5665	1.0263	0.023*
C1	0.35435 (13)	0.44278 (9)	1.09694 (8)	0.0161 (2)
C6	0.61016 (12)	0.13855 (9)	1.06647 (7)	0.0130 (2)
C7	0.70961 (12)	0.03990 (9)	1.04078 (7)	0.0128 (2)
C8	0.80954 (13)	−0.01866 (9)	1.11085 (7)	0.0148 (2)
H8	0.812	0.0028	1.1708	0.018*
C9	0.90254 (13)	−0.10779 (9)	1.08810 (7)	0.0156 (2)
H9	0.9709	−0.1475	1.1325	0.019*
C10	0.89350 (13)	−0.13878 (9)	0.99620 (7)	0.0143 (2)
C11	0.98613 (14)	−0.23014 (10)	0.96740 (8)	0.0182 (2)
H11	1.0548	−0.2727	1.0098	0.022*
C12	0.97515 (14)	−0.25610 (10)	0.87763 (8)	0.0208 (2)
H12	1.0371	−0.3157	0.8593	0.025*
C13	0.86987 (14)	−0.19264 (10)	0.81263 (8)	0.0196 (2)
H13	0.8633	−0.2111	0.7518	0.024*
C14	0.77756 (14)	−0.10438 (9)	0.83805 (7)	0.0165 (2)
H14	0.7078	−0.064	0.7947	0.02*
C15	0.78850 (13)	−0.07462 (9)	0.93054 (7)	0.0133 (2)
N1	0.36061 (13)	0.48153 (9)	1.18100 (7)	0.0199 (2)
N2	0.43161 (11)	0.34266 (8)	1.08430 (6)	0.01391 (19)
N3	0.53164 (11)	0.20051 (8)	0.99536 (6)	0.01377 (19)
N4	0.69803 (11)	0.01543 (7)	0.95409 (6)	0.01317 (18)
N5	0.68666 (12)	0.29972 (8)	1.29263 (6)	0.01620 (19)
O1	0.60217 (10)	0.16082 (7)	1.14574 (5)	0.01639 (17)
O2	0.75498 (11)	0.36208 (7)	1.24246 (6)	0.0224 (2)
O3	0.53418 (10)	0.31398 (7)	1.29794 (5)	0.01974 (18)
O4	0.76463 (11)	0.22297 (7)	1.33845 (6)	0.0228 (2)
H1B	0.326 (2)	0.5477 (16)	1.1861 (12)	0.033 (4)*
H1A	0.423 (2)	0.4444 (15)	1.2254 (12)	0.031 (4)*
H2A	0.481 (2)	0.3072 (15)	1.1296 (12)	0.032 (4)*
H3A	0.5452 (19)	0.1790 (14)	0.9423 (11)	0.026 (4)*

	U11	U22	U33	U12	U13	U23
C5	0.0144 (4)	0.0117 (5)	0.0151 (5)	−0.0008 (4)	0.0036 (4)	−0.0006 (4)
C4	0.0196 (5)	0.0159 (5)	0.0139 (5)	0.0001 (4)	0.0027 (4)	0.0000 (4)
C3	0.0215 (5)	0.0168 (5)	0.0182 (5)	0.0031 (4)	0.0017 (4)	0.0045 (4)
C2	0.0230 (5)	0.0134 (5)	0.0212 (6)	0.0051 (4)	0.0045 (4)	0.0017 (4)
C1	0.0182 (5)	0.0131 (5)	0.0178 (5)	0.0006 (4)	0.0060 (4)	−0.0002 (4)
C6	0.0127 (4)	0.0112 (5)	0.0152 (5)	−0.0015 (4)	0.0018 (4)	−0.0011 (4)
C7	0.0125 (5)	0.0111 (4)	0.0151 (5)	−0.0010 (3)	0.0027 (4)	−0.0007 (4)
C8	0.0152 (5)	0.0165 (5)	0.0129 (5)	−0.0006 (4)	0.0025 (4)	−0.0002 (4)
C9	0.0141 (5)	0.0165 (5)	0.0158 (5)	0.0010 (4)	0.0006 (4)	0.0031 (4)
C10	0.0125 (5)	0.0130 (5)	0.0177 (5)	−0.0005 (4)	0.0034 (4)	0.0004 (4)
C11	0.0164 (5)	0.0160 (5)	0.0219 (6)	0.0037 (4)	0.0018 (4)	0.0007 (4)
C12	0.0198 (5)	0.0165 (5)	0.0268 (6)	0.0041 (4)	0.0062 (4)	−0.0045 (4)
C13	0.0223 (5)	0.0198 (5)	0.0173 (5)	0.0010 (4)	0.0049 (4)	−0.0043 (4)
C14	0.0191 (5)	0.0153 (5)	0.0150 (5)	0.0006 (4)	0.0018 (4)	−0.0003 (4)
C15	0.0130 (4)	0.0115 (5)	0.0156 (5)	−0.0008 (3)	0.0035 (4)	−0.0001 (4)
N1	0.0288 (5)	0.0151 (5)	0.0166 (5)	0.0058 (4)	0.0059 (4)	−0.0011 (4)
N2	0.0171 (4)	0.0119 (4)	0.0129 (4)	0.0021 (3)	0.0027 (3)	0.0005 (3)
N3	0.0175 (4)	0.0120 (4)	0.0122 (4)	0.0018 (3)	0.0033 (3)	−0.0009 (3)
N4	0.0142 (4)	0.0111 (4)	0.0144 (4)	−0.0003 (3)	0.0026 (3)	−0.0008 (3)
N5	0.0221 (5)	0.0142 (4)	0.0121 (4)	−0.0034 (3)	0.0016 (3)	−0.0018 (3)
O1	0.0202 (4)	0.0155 (4)	0.0133 (4)	0.0019 (3)	0.0020 (3)	−0.0023 (3)
O2	0.0317 (5)	0.0184 (4)	0.0195 (4)	−0.0055 (3)	0.0111 (3)	0.0005 (3)
O3	0.0196 (4)	0.0234 (4)	0.0163 (4)	−0.0020 (3)	0.0031 (3)	−0.0002 (3)
O4	0.0269 (4)	0.0182 (4)	0.0206 (4)	−0.0006 (3)	−0.0052 (3)	0.0025 (3)

C5—N2	1.3618 (14)	C9—H9	0.93
C5—C4	1.3758 (15)	C10—C11	1.4183 (15)
C5—N3	1.3842 (13)	C10—C15	1.4246 (15)
C4—C3	1.3974 (15)	C11—C12	1.3690 (17)
C4—H4	0.93	C11—H11	0.93
C3—C2	1.3753 (16)	C12—C13	1.4156 (17)
C3—H3	0.93	C12—H12	0.93
C2—C1	1.4073 (16)	C13—C14	1.3704 (15)
C2—H2	0.93	C13—H13	0.93
C1—N1	1.3332 (15)	C14—C15	1.4191 (15)
C1—N2	1.3633 (14)	C14—H14	0.93
C6—O1	1.2270 (13)	C15—N4	1.3680 (13)
C6—N3	1.3711 (14)	N1—H1B	0.836 (19)
C6—C7	1.4997 (14)	N1—H1A	0.892 (18)
C7—N4	1.3200 (13)	N2—H2A	0.848 (19)
C7—C8	1.4125 (14)	N3—H3A	0.857 (17)
C8—C9	1.3679 (15)	N5—O2	1.2402 (12)
C8—H8	0.93	N5—O4	1.2516 (13)
C9—C10	1.4155 (15)	N5—O3	1.2729 (13)
N2—C5—C4	120.18 (10)	C11—C10—C15	119.15 (10)
N2—C5—N3	118.34 (9)	C12—C11—C10	120.42 (10)
C4—C5—N3	121.46 (10)	C12—C11—H11	119.8
C5—C4—C3	118.15 (10)	C10—C11—H11	119.8
C5—C4—H4	120.9	C11—C12—C13	120.28 (10)
C3—C4—H4	120.9	C11—C12—H12	119.9
C2—C3—C4	121.40 (10)	C13—C12—H12	119.9
C2—C3—H3	119.3	C14—C13—C12	120.90 (10)
C4—C3—H3	119.3	C14—C13—H13	119.5
C3—C2—C1	119.44 (10)	C12—C13—H13	119.5
C3—C2—H2	120.3	C13—C14—C15	119.95 (10)
C1—C2—H2	120.3	C13—C14—H14	120
N1—C1—N2	118.16 (10)	C15—C14—H14	120
N1—C1—C2	124.00 (10)	N4—C15—C14	118.90 (10)
N2—C1—C2	117.84 (10)	N4—C15—C10	121.82 (10)
O1—C6—N3	123.59 (10)	C14—C15—C10	119.28 (10)
O1—C6—C7	121.40 (9)	C1—N1—H1B	116.0 (12)
N3—C6—C7	115.01 (9)	C1—N1—H1A	118.4 (11)
N4—C7—C8	125.13 (10)	H1B—N1—H1A	123.6 (16)
N4—C7—C6	117.22 (9)	C5—N2—C1	122.93 (10)
C8—C7—C6	117.65 (9)	C5—N2—H2A	117.6 (12)
C9—C8—C7	118.16 (10)	C1—N2—H2A	119.4 (12)
C9—C8—H8	120.9	C6—N3—C5	126.27 (9)
C7—C8—H8	120.9	C6—N3—H3A	117.0 (11)
C8—C9—C10	119.18 (10)	C5—N3—H3A	116.6 (11)
C8—C9—H9	120.4	C7—N4—C15	117.29 (9)
C10—C9—H9	120.4	O2—N5—O4	121.37 (10)
C9—C10—C11	122.44 (10)	O2—N5—O3	119.49 (9)
C9—C10—C15	118.40 (9)	O4—N5—O3	119.14 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.892 (18)	2.019 (19)	2.8721 (14)	159.7 (16)
N1—H1B···O4i	0.836 (19)	2.204 (19)	3.0202 (14)	165.1 (16)
N2—H2A···O1	0.848 (19)	1.984 (18)	2.6458 (12)	134.1 (16)
N2—H2A···O3	0.848 (19)	2.496 (18)	3.2058 (12)	141.7 (15)
N3—H3A···O3ii	0.857 (17)	2.153 (17)	2.9652 (12)	158.2 (15)
N3—H3A···N4	0.857 (17)	2.288 (16)	2.6879 (15)	108.7 (13)
C4—H4···O3ii	0.93	2.44	3.1947 (14)	138
C11—H11···O4iii	0.93	2.53	3.3460 (14)	147
C12—H12···O2iv	0.93	2.5	3.2901 (14)	142
C14—H14···O2ii	0.93	2.55	3.1840 (14)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.892 (18)	2.019 (19)	2.8721 (14)	159.7 (16)
N1—H1B⋯O4i	0.836 (19)	2.204 (19)	3.0202 (14)	165.1 (16)
N2—H2A⋯O1	0.848 (19)	1.984 (18)	2.6458 (12)	134.1 (16)
N2—H2A⋯O3	0.848 (19)	2.496 (18)	3.2058 (12)	141.7 (15)
N3—H3A⋯O3ii	0.857 (17)	2.153 (17)	2.9652 (12)	158.2 (15)
N3—H3A⋯N4	0.857 (17)	2.288 (16)	2.6879 (15)	108.7 (13)
C4—H4⋯O3ii	0.93	2.44	3.1947 (14)	138
C11—H11⋯O4iii	0.93	2.53	3.3460 (14)	147
C12—H12⋯O2iv	0.93	2.5	3.2901 (14)	142
C14—H14⋯O2ii	0.93	2.55	3.1840 (14)	126

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