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Acta Cryst. (2008). E64, o990    [ doi:10.1107/S1600536808012579 ]

2-(2-Quinolyl)quinolinium nitrate

A. Abedi, A. Bahrami Shabestari and V. Amani

Abstract top

In the cation of the title compound, C18H13N2+·NO3-, the two bicyclic ring systems form a dihedral angle of 3.84 (4)°. The nitrate anion is disordered over two orientations in a 0.9:0.1 ratio. In the crystal structure, the cations form stacks along the a axis, with short intermolecular contacts [C...C = 3.330 (3) and 3.345 (4) Å], and link to the anions via N-H...O hydrogen bonds.

Comment top

In recent years, there has been considerable interest in proton transfer systems and their structures (Smith et al., 1999; Zafar et al., 2000; Rafizadeh et al., 2006; Yousefi et al., 2007). To our knowledge, there is only one proton-transfer system with 2,2'-biquinolinyl, such as [(biq.H)(I2Cl3)] [biq.H = 2-(2-quinolinyl)quinolinium], which was structurally characterized (Parlow & Hartl, 1979). Herewith we report the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of (I) contains one cation and one anion (Fig. 1). In the cation, two bicycles form a dihedral angle of 3.84 (4)%. In the crystal structure, the cations form stacks along the a axis with short intermolecular contacts [C···C = 3.330 (3) and 3.345 (4)Å] linking the anions via N—H···O hydrogen bonds.

Related literature top

For related literature, see: Smith et al. (1999); Zafar et al. (2000); Rafizadeh et al. (2006); Yousefi et al. (2007); Parlow & Hartl (1979).

Experimental top

For the preparation of the title compound, (I), a solution of 2,2'-biquinolinyl (0.20 g, 0.78 mmol) in HNO3 0.5 M (10 ml) was added to a solution of La(NO3)3.6H2O, (0.11 g, 0.26 mmol) in water (5 ml) and the resulting yellow solution was stirred at 333 K for 2 h. Then, it was left to evaporate slowly at room temperature. The suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion in a solution of yellow precipitated in DMSO after one week (yield 0.19 g, 76.2%, m.p 496–497 K).

Refinement top

C-bound H atoms were geometrically positioned (C-H 0.95 Å). The H atom of NH group was located on a difference Fourier map, but placed in idealized position (N-H 0.91 Å). All H atoms were refined in riding model approximation, with Uiso(H) = 1.2 Ueq of the parent atom. The NO3 anion was treated as disordered between two orientations with the occupancies fixed to 0.9 and 0.1, respectively.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The content of asymmetric unit of (I) showing the atomic numbering and 50% probability displacement ellipsoids. Only major part of the disordered nitrate anion is shown.
2-(2-Quinolyl)quinolinium nitrate top
Crystal data top
C18H13N2+·NO3–F000 = 664
Mr = 319.31Dx = 1.499 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 937 reflections
a = 6.9756 (6) Åθ = 3–29º
b = 10.6408 (9) ŵ = 0.11 mm−1
c = 19.1226 (15) ÅT = 120 (2) K
β = 94.399 (2)ºBlock, yellow
V = 1415.2 (2) Å30.45 × 0.30 × 0.25 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2115 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.038
Monochromator: graphiteθmax = 29.0º
T = 120(2) Kθmin = 2.1º
ω scansh = −9→9
Absorption correction: nonek = −14→14
15078 measured reflectionsl = −25→26
3739 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.136  w = 1/[σ2(Fo2) + (0.0551P)2 + 0.46P]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3739 reflectionsΔρmax = 0.31 e Å−3
229 parametersΔρmin = −0.29 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C18H13N2+·NO3–V = 1415.2 (2) Å3
Mr = 319.31Z = 4
Monoclinic, P21/cMo Kα
a = 6.9756 (6) ŵ = 0.11 mm−1
b = 10.6408 (9) ÅT = 120 (2) K
c = 19.1226 (15) Å0.45 × 0.30 × 0.25 mm
β = 94.399 (2)º
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		3739 independent reflections
Absorption correction: none2115 reflections with I > 2σ(I)
15078 measured reflectionsRint = 0.038
Refinement top
R[F2 > 2σ(F2)] = 0.0573 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 0.97Δρmax = 0.31 e Å−3
3739 reflectionsΔρmin = −0.29 e Å−3
229 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.2846 (2)0.12303 (14)0.47447 (7)0.0261 (3)
N20.21783 (19)−0.05200 (13)0.56913 (7)0.0245 (3)
H2N0.22490.03160.58020.029*
C10.3241 (2)0.21681 (17)0.42885 (9)0.0265 (4)
C20.3386 (3)0.34167 (17)0.45393 (10)0.0320 (4)
H2A0.31800.35930.50150.038*
C30.3821 (3)0.43694 (19)0.41010 (10)0.0352 (5)
H3A0.39200.52050.42740.042*
C40.4124 (3)0.4124 (2)0.33902 (10)0.0347 (5)
H4A0.44480.47940.30930.042*
C50.3955 (3)0.29307 (19)0.31289 (10)0.0329 (4)
H5A0.41270.27800.26480.040*
C60.3524 (2)0.19166 (18)0.35718 (9)0.0283 (4)
C70.3393 (3)0.06604 (19)0.33471 (9)0.0319 (4)
H7A0.35530.04600.28710.038*
C80.3037 (3)−0.02721 (18)0.38088 (9)0.0307 (4)
H8A0.2981−0.11260.36630.037*
C90.2754 (2)0.00614 (17)0.45085 (9)0.0243 (4)
C100.2313 (2)−0.09095 (17)0.50285 (9)0.0249 (4)
C110.2028 (3)−0.21806 (17)0.48705 (10)0.0309 (4)
H11A0.2123−0.24710.44050.037*
C120.1613 (3)−0.30107 (17)0.53859 (10)0.0321 (4)
H12A0.1413−0.38730.52730.038*
C130.1480 (2)−0.26001 (17)0.60813 (9)0.0272 (4)
C140.1044 (2)−0.34060 (17)0.66293 (10)0.0313 (4)
H14A0.0826−0.42740.65390.038*
C150.0931 (3)−0.29430 (18)0.72935 (10)0.0332 (4)
H15A0.0621−0.34920.76600.040*
C160.1272 (3)−0.16592 (18)0.74375 (10)0.0326 (4)
H16A0.1207−0.13550.79020.039*
C170.1696 (2)−0.08437 (17)0.69156 (9)0.0285 (4)
H17A0.19280.00200.70150.034*
C180.1781 (2)−0.13100 (17)0.62339 (9)0.0248 (4)
N30.2376 (3)0.27946 (17)0.62588 (8)0.0385 (4)
O10.1506 (3)0.17769 (16)0.63037 (10)0.0433 (5)0.90
O20.1410 (3)0.37683 (15)0.60925 (9)0.0502 (5)0.90
O30.4157 (3)0.2874 (2)0.63555 (9)0.0555 (5)0.90
O1'0.0850 (18)0.2168 (18)0.6230 (13)0.060 (7)*0.10
O2'0.264 (3)0.3897 (8)0.6450 (11)0.077 (6)*0.10
O3'0.3749 (19)0.2024 (14)0.6346 (9)0.054 (4)*0.10
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0253 (8)0.0271 (8)0.0258 (8)0.0003 (6)0.0022 (6)0.0036 (6)
N20.0255 (8)0.0229 (7)0.0249 (8)0.0000 (6)0.0011 (6)−0.0003 (6)
C10.0239 (9)0.0306 (10)0.0249 (9)0.0021 (7)0.0017 (7)0.0031 (8)
C20.0371 (11)0.0314 (10)0.0280 (10)0.0010 (8)0.0063 (8)0.0017 (8)
C30.0368 (11)0.0306 (10)0.0384 (11)0.0008 (8)0.0044 (9)0.0054 (8)
C40.0289 (10)0.0431 (12)0.0323 (10)0.0004 (8)0.0027 (8)0.0144 (9)
C50.0274 (10)0.0473 (12)0.0239 (9)0.0000 (9)0.0010 (7)0.0069 (8)
C60.0214 (9)0.0393 (11)0.0243 (9)0.0021 (8)0.0014 (7)0.0027 (8)
C70.0286 (10)0.0442 (12)0.0230 (9)−0.0017 (8)0.0035 (7)−0.0013 (8)
C80.0329 (10)0.0318 (10)0.0273 (10)−0.0010 (8)0.0029 (8)−0.0046 (8)
C90.0214 (8)0.0288 (9)0.0226 (8)0.0006 (7)0.0001 (7)−0.0005 (7)
C100.0203 (8)0.0292 (10)0.0251 (9)0.0016 (7)0.0013 (7)−0.0017 (7)
C110.0332 (10)0.0299 (10)0.0295 (10)0.0002 (8)0.0026 (8)−0.0047 (8)
C120.0310 (10)0.0240 (9)0.0412 (11)−0.0010 (8)0.0029 (8)−0.0041 (8)
C130.0215 (9)0.0282 (9)0.0319 (10)0.0015 (7)0.0027 (7)0.0018 (8)
C140.0280 (10)0.0241 (9)0.0417 (11)−0.0014 (7)0.0024 (8)0.0046 (8)
C150.0290 (10)0.0336 (10)0.0375 (11)−0.0009 (8)0.0053 (8)0.0118 (8)
C160.0339 (10)0.0364 (11)0.0278 (10)0.0036 (8)0.0048 (8)0.0024 (8)
C170.0287 (10)0.0288 (9)0.0282 (9)0.0013 (8)0.0027 (7)−0.0003 (8)
C180.0203 (8)0.0258 (9)0.0283 (9)0.0016 (7)0.0017 (7)0.0036 (7)
N30.0534 (11)0.0360 (10)0.0272 (9)−0.0011 (9)0.0102 (8)−0.0040 (7)
O10.0697 (12)0.0249 (9)0.0380 (10)−0.0089 (10)0.0211 (9)−0.0020 (8)
O20.0790 (13)0.0276 (9)0.0460 (10)0.0114 (9)0.0186 (9)0.0005 (7)
O30.0514 (12)0.0705 (14)0.0440 (11)−0.0145 (10)0.0011 (8)0.0099 (9)
Geometric parameters (Å, °) top
N1—C91.323 (2)C10—C111.397 (3)
N1—C11.367 (2)C11—C121.371 (3)
N2—C101.344 (2)C11—H11A0.9500
N2—C181.380 (2)C12—C131.410 (3)
N2—H2N0.910C12—H12A0.9500
C1—C21.413 (3)C13—C141.405 (2)
C1—C61.425 (2)C13—C181.416 (3)
C2—C31.364 (3)C14—C151.370 (3)
C2—H2A0.9500C14—H14A0.9500
C3—C41.416 (3)C15—C161.410 (3)
C3—H3A0.9500C15—H15A0.9500
C4—C51.366 (3)C16—C171.372 (3)
C4—H4A0.9500C16—H16A0.9500
C5—C61.418 (3)C17—C181.400 (2)
C5—H5A0.9500C17—H17A0.9500
C6—C71.405 (3)N3—O2'1.239 (5)
C7—C81.364 (3)N3—O31.245 (2)
C7—H7A0.9500N3—O11.247 (2)
C8—C91.413 (2)N3—O1'1.253 (5)
C8—H8A0.9500N3—O3'1.263 (5)
C9—C101.483 (2)N3—O21.263 (2)
N1···C18i3.606 (3)C6···C14i3.550 (4)
N1···C10ii3.388 (3)C18···C6ii3.330 (3)
C1···C13i3.345 (4)
C9—N1—C1118.36 (15)N2—C10—C9116.81 (15)
C10—N2—C18123.64 (15)C11—C10—C9124.27 (16)
C10—N2—H2N120.8C12—C11—C10120.19 (17)
C18—N2—H2N115.4C12—C11—H11A119.9
N1—C1—C2118.83 (16)C10—C11—H11A119.9
N1—C1—C6121.75 (16)C11—C12—C13120.75 (17)
C2—C1—C6119.42 (16)C11—C12—H12A119.6
C3—C2—C1120.24 (17)C13—C12—H12A119.6
C3—C2—H2A119.9C14—C13—C12123.24 (17)
C1—C2—H2A119.9C14—C13—C18118.36 (17)
C2—C3—C4120.60 (19)C12—C13—C18118.40 (16)
C2—C3—H3A119.7C15—C14—C13120.20 (17)
C4—C3—H3A119.7C15—C14—H14A119.9
C5—C4—C3120.51 (18)C13—C14—H14A119.9
C5—C4—H4A119.7C14—C15—C16120.56 (17)
C3—C4—H4A119.7C14—C15—H15A119.7
C4—C5—C6120.33 (17)C16—C15—H15A119.7
C4—C5—H5A119.8C17—C16—C15120.89 (18)
C6—C5—H5A119.8C17—C16—H16A119.6
C7—C6—C5123.57 (17)C15—C16—H16A119.6
C7—C6—C1117.54 (16)C16—C17—C18118.69 (17)
C5—C6—C1118.88 (17)C16—C17—H17A120.7
C8—C7—C6120.34 (17)C18—C17—H17A120.7
C8—C7—H7A119.8N2—C18—C17120.62 (16)
C6—C7—H7A119.8N2—C18—C13118.09 (16)
C7—C8—C9118.43 (17)C17—C18—C13121.29 (16)
C7—C8—H8A120.8O3—N3—O1122.3 (2)
C9—C8—H8A120.8O2'—N3—O1'128.7 (14)
N1—C9—C8123.57 (16)O2'—N3—O3'118.7 (14)
N1—C9—C10115.67 (15)O1'—N3—O3'107.1 (13)
C8—C9—C10120.77 (16)O3—N3—O2119.2 (2)
N2—C10—C11118.92 (16)O1—N3—O2118.5 (2)
C9—N1—C1—C2−178.56 (16)N1—C9—C10—N2−4.2 (2)
C9—N1—C1—C60.9 (2)C8—C9—C10—N2176.18 (15)
N1—C1—C2—C3178.55 (17)N1—C9—C10—C11175.52 (16)
C6—C1—C2—C3−1.0 (3)C8—C9—C10—C11−4.1 (3)
C1—C2—C3—C40.3 (3)N2—C10—C11—C120.2 (3)
C2—C3—C4—C51.1 (3)C9—C10—C11—C12−179.57 (16)
C3—C4—C5—C6−1.7 (3)C10—C11—C12—C13−0.4 (3)
C4—C5—C6—C7−177.72 (18)C11—C12—C13—C14179.46 (17)
C4—C5—C6—C11.0 (3)C11—C12—C13—C180.2 (3)
N1—C1—C6—C7−0.3 (3)C12—C13—C14—C15−179.80 (17)
C2—C1—C6—C7179.14 (16)C18—C13—C14—C15−0.5 (3)
N1—C1—C6—C5−179.15 (16)C13—C14—C15—C16−0.7 (3)
C2—C1—C6—C50.3 (3)C14—C15—C16—C170.9 (3)
C5—C6—C7—C8177.74 (17)C15—C16—C17—C180.1 (3)
C1—C6—C7—C8−1.0 (3)C10—N2—C18—C17178.81 (15)
C6—C7—C8—C91.7 (3)C10—N2—C18—C13−0.6 (2)
C1—N1—C9—C8−0.2 (2)C16—C17—C18—N2179.18 (16)
C1—N1—C9—C10−179.75 (15)C16—C17—C18—C13−1.4 (3)
C7—C8—C9—N1−1.1 (3)C14—C13—C18—N2−178.98 (15)
C7—C8—C9—C10178.41 (16)C12—C13—C18—N20.3 (2)
C18—N2—C10—C110.4 (2)C14—C13—C18—C171.6 (2)
C18—N2—C10—C9−179.86 (14)C12—C13—C18—C17−179.08 (16)
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.911.922.766 (2)153
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.911.922.766 (2)153
Acknowledgements top

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

references
References top

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Smith, G., Pascoe, C. E., Kennard, C. H. L. & Byriel, K. A. (1999). Aust. J. Chem. 52, 71–74.

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Zafar, A., Geib, S. J., Hamuro, Y., Carr, A. J. & Hamilton, A. D. (2000). Tetrahedron, 56, 8419–8427.