2-Cyano-quinolin-1-ium nitrate.

A proton is transferred from the nitric acid to the N atom of 2-cyano-quinoline during crystallization, resulting in the formation of the title salt, C(10)H(7)N(2) (+)·NO(3) (-). The quinolinium ring system is approximately planar, with a maximum deviation of 0.013 (3) Å. In the crystal, a very asymmetric bifurcated N-H⋯(O,O) hydrogen bond to two O atoms of an adjacent nitrate anion occurs, generating an R(2) (1)(4) ring motif. C-H⋯O hydrogen bonds link the ions into sheets stacking along the a axis.

Related literature

For background to and the biological activities of quinoline derivatives, see: Loh, Quah et al. (2010a ▶,b ▶); Loh et al. (2010 ▶); Sasaki et al. (1998 ▶); Reux et al. (2009 ▶); Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1988 ▶). For the hydrogen-bond motif, see: Bernstein et al. (1995 ▶). For related structures, see: Loh, Quah et al. (2010a ▶,b ▶); Loh et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H7N2 +·NO3 −

M = 217.19

Monoclinic,

a = 3.6969 (1) Å

b = 17.7031 (3) Å

c = 14.6029 (2) Å

β = 95.802 (1)°

V = 950.81 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.44 × 0.18 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.951, T max = 0.992

16184 measured reflections

2758 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.122

S = 1.05

2758 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039243/hb5669sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039243/hb5669Isup2.hkl

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

C10H7N2+·NO3−	F(000) = 448
Mr = 217.19	Dx = 1.517 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3861 reflections
a = 3.6969 (1) Å	θ = 2.7–31.0°
b = 17.7031 (3) Å	µ = 0.12 mm−1
c = 14.6029 (2) Å	T = 100 K
β = 95.802 (1)°	Plate, colourless
V = 950.81 (3) Å3	0.44 × 0.18 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2758 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.951, Tmax = 0.992	k = −24→24
16184 measured reflections	l = −20→20

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.2227P] where P = (Fo2 + 2Fc2)/3
2758 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.1851 (3)	0.21342 (6)	0.92466 (7)	0.0314 (3)
O2	0.4106 (3)	0.10064 (5)	0.91484 (7)	0.0255 (3)
O3	0.4296 (3)	0.17922 (5)	0.80150 (6)	0.0258 (3)
N1	0.2524 (3)	0.30942 (6)	0.73844 (7)	0.0144 (2)
H1N1	0.3241	0.2630	0.7672	0.079 (8)*
N2	−0.1335 (4)	0.17939 (7)	0.58610 (8)	0.0265 (3)
N3	0.3373 (3)	0.16413 (6)	0.88321 (7)	0.0196 (3)
C1	0.3582 (3)	0.37566 (7)	0.78076 (8)	0.0142 (3)
C2	0.5593 (4)	0.37429 (7)	0.86850 (8)	0.0161 (3)
C3	0.6627 (4)	0.44133 (7)	0.90990 (9)	0.0176 (3)
C4	0.5697 (4)	0.51140 (7)	0.86660 (9)	0.0181 (3)
C5	0.3739 (4)	0.51378 (7)	0.78226 (9)	0.0175 (3)
C6	0.2637 (3)	0.44559 (7)	0.73637 (8)	0.0148 (3)
C7	0.0675 (4)	0.44419 (7)	0.64838 (9)	0.0176 (3)
C8	−0.0316 (4)	0.37627 (7)	0.60703 (9)	0.0175 (3)
C9	0.0658 (4)	0.30972 (7)	0.65509 (8)	0.0158 (3)
C10	−0.0406 (4)	0.23670 (7)	0.61661 (9)	0.0184 (3)
H2A	0.619 (4)	0.3267 (9)	0.8975 (11)	0.020 (4)*
H3A	0.805 (5)	0.4406 (9)	0.9717 (12)	0.023 (4)*
H4A	0.649 (5)	0.5595 (10)	0.8975 (11)	0.028 (4)*
H5A	0.304 (5)	0.5598 (9)	0.7531 (11)	0.024 (4)*
H7A	0.002 (4)	0.4918 (9)	0.6174 (11)	0.020 (4)*
H8A	−0.166 (5)	0.3735 (10)	0.5461 (13)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0486 (7)	0.0188 (5)	0.0295 (6)	0.0018 (5)	0.0167 (5)	−0.0018 (4)
O2	0.0375 (6)	0.0142 (5)	0.0234 (5)	−0.0007 (4)	−0.0040 (4)	0.0047 (4)
O3	0.0438 (7)	0.0173 (5)	0.0170 (5)	0.0075 (4)	0.0072 (4)	0.0026 (4)
N1	0.0169 (6)	0.0120 (5)	0.0142 (5)	0.0006 (4)	0.0010 (4)	0.0000 (4)
N2	0.0331 (7)	0.0217 (6)	0.0237 (6)	−0.0029 (5)	−0.0020 (5)	−0.0014 (5)
N3	0.0255 (6)	0.0153 (5)	0.0172 (5)	−0.0027 (4)	−0.0015 (4)	−0.0003 (4)
C1	0.0146 (6)	0.0126 (6)	0.0159 (6)	0.0002 (4)	0.0035 (5)	−0.0005 (4)
C2	0.0180 (6)	0.0145 (6)	0.0156 (6)	0.0004 (5)	0.0013 (5)	0.0005 (4)
C3	0.0164 (6)	0.0187 (6)	0.0177 (6)	−0.0017 (5)	0.0020 (5)	−0.0024 (5)
C4	0.0180 (7)	0.0151 (6)	0.0216 (6)	−0.0035 (5)	0.0044 (5)	−0.0037 (5)
C5	0.0200 (7)	0.0128 (6)	0.0204 (6)	0.0002 (5)	0.0053 (5)	0.0002 (5)
C6	0.0146 (6)	0.0140 (6)	0.0160 (6)	0.0009 (4)	0.0027 (5)	0.0008 (4)
C7	0.0185 (7)	0.0166 (6)	0.0177 (6)	0.0030 (5)	0.0023 (5)	0.0023 (5)
C8	0.0179 (6)	0.0192 (6)	0.0153 (6)	0.0016 (5)	0.0008 (5)	0.0009 (5)
C9	0.0157 (6)	0.0159 (6)	0.0158 (6)	−0.0003 (5)	0.0017 (5)	−0.0016 (4)
C10	0.0190 (7)	0.0192 (6)	0.0166 (6)	0.0004 (5)	0.0003 (5)	0.0005 (5)

O1—N3	1.2301 (15)	C3—H3A	0.998 (17)
O2—N3	1.2347 (14)	C4—C5	1.3646 (19)
O3—N3	1.3015 (14)	C4—H4A	0.993 (18)
N1—C9	1.3370 (16)	C5—C6	1.4203 (17)
N1—C1	1.3642 (15)	C5—H5A	0.943 (17)
N1—H1N1	0.9481	C6—C7	1.4104 (18)
N2—C10	1.1466 (18)	C7—C8	1.3784 (18)
C1—C2	1.4152 (17)	C7—H7A	0.976 (17)
C1—C6	1.4243 (16)	C8—C9	1.3998 (18)
C2—C3	1.3686 (18)	C8—H8A	0.977 (18)
C2—H2A	0.959 (16)	C9—C10	1.4480 (18)
C3—C4	1.4188 (18)
C9—N1—C1	120.45 (10)	C3—C4—H4A	119.9 (10)
C9—N1—H1N1	120.2	C4—C5—C6	120.01 (12)
C1—N1—H1N1	119.3	C4—C5—H5A	122.1 (10)
O1—N3—O2	123.76 (12)	C6—C5—H5A	117.9 (10)
O1—N3—O3	118.74 (11)	C7—C6—C5	122.77 (11)
O2—N3—O3	117.50 (11)	C7—C6—C1	118.63 (11)
N1—C1—C2	119.72 (11)	C5—C6—C1	118.60 (12)
N1—C1—C6	119.68 (11)	C8—C7—C6	120.25 (12)
C2—C1—C6	120.60 (11)	C8—C7—H7A	120.5 (10)
C3—C2—C1	118.87 (12)	C6—C7—H7A	119.2 (10)
C3—C2—H2A	121.7 (10)	C7—C8—C9	118.10 (12)
C1—C2—H2A	119.4 (10)	C7—C8—H8A	122.1 (10)
C2—C3—C4	121.13 (12)	C9—C8—H8A	119.8 (10)
C2—C3—H3A	119.1 (9)	N1—C9—C8	122.87 (11)
C4—C3—H3A	119.8 (9)	N1—C9—C10	116.40 (11)
C5—C4—C3	120.79 (12)	C8—C9—C10	120.72 (12)
C5—C4—H4A	119.3 (10)	N2—C10—C9	178.33 (15)
C9—N1—C1—C2	−179.23 (11)	C2—C1—C6—C7	179.11 (11)
C9—N1—C1—C6	1.04 (18)	N1—C1—C6—C5	179.37 (11)
N1—C1—C2—C3	−179.94 (12)	C2—C1—C6—C5	−0.36 (18)
C6—C1—C2—C3	−0.21 (19)	C5—C6—C7—C8	179.86 (12)
C1—C2—C3—C4	0.39 (19)	C1—C6—C7—C8	0.40 (19)
C2—C3—C4—C5	0.0 (2)	C6—C7—C8—C9	0.44 (19)
C3—C4—C5—C6	−0.6 (2)	C1—N1—C9—C8	−0.16 (19)
C4—C5—C6—C7	−178.69 (12)	C1—N1—C9—C10	−178.81 (11)
C4—C5—C6—C1	0.76 (19)	C7—C8—C9—N1	−0.6 (2)
N1—C1—C6—C7	−1.15 (18)	C7—C8—C9—C10	177.99 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.95	2.56	3.2376 (15)	128
N1—H1N1···O3	0.95	1.60	2.5432 (14)	172
C5—H5A···O3i	0.943 (16)	2.497 (16)	3.2835 (16)	141.0 (15)
C7—H7A···O2ii	0.976 (16)	2.473 (16)	3.3641 (16)	151.8 (12)
C8—H8A···O2iii	0.977 (18)	2.391 (19)	3.3355 (17)	162.4 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.95	2.56	3.2376 (15)	128
N1—H1N1⋯O3	0.95	1.60	2.5432 (14)	172
C5—H5A⋯O3i	0.943 (16)	2.497 (16)	3.2835 (16)	141.0 (15)
C7—H7A⋯O2ii	0.976 (16)	2.473 (16)	3.3641 (16)	151.8 (12)
C8—H8A⋯O2iii	0.977 (18)	2.391 (19)	3.3355 (17)	162.4 (15)

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