2-(2-Quinol­yl)quinolinium nitrate

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

doi:10.1107/S1600536808012579

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o990

doi:10.1107/S1600536808012579

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2-(2-Quinolyl)quinolinium nitrate

Anita Abedi,^a Arezoo Bahrami Shabestari ^a and Vahid Amani ^b ^*

^aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^bDepartment of Chemistry, Islamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
^*Correspondence e-mail: v_amani2002@yahoo.com

(Received 17 April 2008; accepted 29 April 2008; online 3 May 2008)

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.

Related literature

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

Experimental

Crystal data

C₁₈H₁₃N₂⁺·NO₃⁻
M_r = 319.31
Monoclinic, P 2₁ /c
a = 6.9756 (6) Å
b = 10.6408 (9) Å
c = 19.1226 (15) Å
β = 94.399 (2)°
V = 1415.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 (2) K
0.45 × 0.30 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: none
15078 measured reflections
3739 independent reflections
2115 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.136
S = 0.97
3739 reflections
229 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1	0.91	1.92	2.766 (2)	153

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012579/cv2401sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012579/cv2401Isup2.hkl

checkCIF report

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).

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

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⁻	F(000) = 664
M_r = 319.31	D_x = 1.499 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 937 reflections
a = 6.9756 (6) Å	θ = 3–29°
b = 10.6408 (9) Å	µ = 0.11 mm⁻¹
c = 19.1226 (15) Å	T = 120 K
β = 94.399 (2)°	Block, yellow
V = 1415.2 (2) Å³	0.45 × 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 tube	R_int = 0.038
Graphite monochromator	θ_max = 29.0°, θ_min = 2.1°
ω scans	h = −9→9
15078 measured reflections	k = −14→14
3739 independent reflections	l = −25→26

Refinement top

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)] = 0.057	Hydrogen site location: mixed
wR(F²) = 0.136	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0551P)² + 0.46P] where P = (F_o² + 2F_c²)/3
3739 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.31 e Å⁻³
3 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₈H₁₃N₂⁺·NO₃⁻	V = 1415.2 (2) Å³
M_r = 319.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9756 (6) Å	µ = 0.11 mm⁻¹
b = 10.6408 (9) Å	T = 120 K
c = 19.1226 (15) Å	0.45 × 0.30 × 0.25 mm
β = 94.399 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2115 reflections with I > 2σ(I)
15078 measured reflections	R_int = 0.038
3739 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	3 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 0.97	Δρ_max = 0.31 e Å⁻³
3739 reflections	Δρ_min = −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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.2846 (2)	0.12303 (14)	0.47447 (7)	0.0261 (3)
N2	0.21783 (19)	−0.05200 (13)	0.56913 (7)	0.0245 (3)
H2N	0.2249	0.0316	0.5802	0.029*
C1	0.3241 (2)	0.21681 (17)	0.42885 (9)	0.0265 (4)
C2	0.3386 (3)	0.34167 (17)	0.45393 (10)	0.0320 (4)
H2A	0.3180	0.3593	0.5015	0.038*
C3	0.3821 (3)	0.43694 (19)	0.41010 (10)	0.0352 (5)
H3A	0.3920	0.5205	0.4274	0.042*
C4	0.4124 (3)	0.4124 (2)	0.33902 (10)	0.0347 (5)
H4A	0.4448	0.4794	0.3093	0.042*
C5	0.3955 (3)	0.29307 (19)	0.31289 (10)	0.0329 (4)
H5A	0.4127	0.2780	0.2648	0.040*
C6	0.3524 (2)	0.19166 (18)	0.35718 (9)	0.0283 (4)
C7	0.3393 (3)	0.06604 (19)	0.33471 (9)	0.0319 (4)
H7A	0.3553	0.0460	0.2871	0.038*
C8	0.3037 (3)	−0.02721 (18)	0.38088 (9)	0.0307 (4)
H8A	0.2981	−0.1126	0.3663	0.037*
C9	0.2754 (2)	0.00614 (17)	0.45085 (9)	0.0243 (4)
C10	0.2313 (2)	−0.09095 (17)	0.50285 (9)	0.0249 (4)
C11	0.2028 (3)	−0.21806 (17)	0.48705 (10)	0.0309 (4)
H11A	0.2123	−0.2471	0.4405	0.037*
C12	0.1613 (3)	−0.30107 (17)	0.53859 (10)	0.0321 (4)
H12A	0.1413	−0.3873	0.5273	0.038*
C13	0.1480 (2)	−0.26001 (17)	0.60813 (9)	0.0272 (4)
C14	0.1044 (2)	−0.34060 (17)	0.66293 (10)	0.0313 (4)
H14A	0.0826	−0.4274	0.6539	0.038*
C15	0.0931 (3)	−0.29430 (18)	0.72935 (10)	0.0332 (4)
H15A	0.0621	−0.3492	0.7660	0.040*
C16	0.1272 (3)	−0.16592 (18)	0.74375 (10)	0.0326 (4)
H16A	0.1207	−0.1355	0.7902	0.039*
C17	0.1696 (2)	−0.08437 (17)	0.69156 (9)	0.0285 (4)
H17A	0.1928	0.0020	0.7015	0.034*
C18	0.1781 (2)	−0.13100 (17)	0.62339 (9)	0.0248 (4)
N3	0.2376 (3)	0.27946 (17)	0.62588 (8)	0.0385 (4)
O1	0.1506 (3)	0.17769 (16)	0.63037 (10)	0.0433 (5)	0.90
O2	0.1410 (3)	0.37683 (15)	0.60925 (9)	0.0502 (5)	0.90
O3	0.4157 (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

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0253 (8)	0.0271 (8)	0.0258 (8)	0.0003 (6)	0.0022 (6)	0.0036 (6)
N2	0.0255 (8)	0.0229 (7)	0.0249 (8)	0.0000 (6)	0.0011 (6)	−0.0003 (6)
C1	0.0239 (9)	0.0306 (10)	0.0249 (9)	0.0021 (7)	0.0017 (7)	0.0031 (8)
C2	0.0371 (11)	0.0314 (10)	0.0280 (10)	0.0010 (8)	0.0063 (8)	0.0017 (8)
C3	0.0368 (11)	0.0306 (10)	0.0384 (11)	0.0008 (8)	0.0044 (9)	0.0054 (8)
C4	0.0289 (10)	0.0431 (12)	0.0323 (10)	0.0004 (8)	0.0027 (8)	0.0144 (9)
C5	0.0274 (10)	0.0473 (12)	0.0239 (9)	0.0000 (9)	0.0010 (7)	0.0069 (8)
C6	0.0214 (9)	0.0393 (11)	0.0243 (9)	0.0021 (8)	0.0014 (7)	0.0027 (8)
C7	0.0286 (10)	0.0442 (12)	0.0230 (9)	−0.0017 (8)	0.0035 (7)	−0.0013 (8)
C8	0.0329 (10)	0.0318 (10)	0.0273 (10)	−0.0010 (8)	0.0029 (8)	−0.0046 (8)
C9	0.0214 (8)	0.0288 (9)	0.0226 (8)	0.0006 (7)	0.0001 (7)	−0.0005 (7)
C10	0.0203 (8)	0.0292 (10)	0.0251 (9)	0.0016 (7)	0.0013 (7)	−0.0017 (7)
C11	0.0332 (10)	0.0299 (10)	0.0295 (10)	0.0002 (8)	0.0026 (8)	−0.0047 (8)
C12	0.0310 (10)	0.0240 (9)	0.0412 (11)	−0.0010 (8)	0.0029 (8)	−0.0041 (8)
C13	0.0215 (9)	0.0282 (9)	0.0319 (10)	0.0015 (7)	0.0027 (7)	0.0018 (8)
C14	0.0280 (10)	0.0241 (9)	0.0417 (11)	−0.0014 (7)	0.0024 (8)	0.0046 (8)
C15	0.0290 (10)	0.0336 (10)	0.0375 (11)	−0.0009 (8)	0.0053 (8)	0.0118 (8)
C16	0.0339 (10)	0.0364 (11)	0.0278 (10)	0.0036 (8)	0.0048 (8)	0.0024 (8)
C17	0.0287 (10)	0.0288 (9)	0.0282 (9)	0.0013 (8)	0.0027 (7)	−0.0003 (8)
C18	0.0203 (8)	0.0258 (9)	0.0283 (9)	0.0016 (7)	0.0017 (7)	0.0036 (7)
N3	0.0534 (11)	0.0360 (10)	0.0272 (9)	−0.0011 (9)	0.0102 (8)	−0.0040 (7)
O1	0.0697 (12)	0.0249 (9)	0.0380 (10)	−0.0089 (10)	0.0211 (9)	−0.0020 (8)
O2	0.0790 (13)	0.0276 (9)	0.0460 (10)	0.0114 (9)	0.0186 (9)	0.0005 (7)
O3	0.0514 (12)	0.0705 (14)	0.0440 (11)	−0.0145 (10)	0.0011 (8)	0.0099 (9)

Geometric parameters (Å, º) top

N1—C9	1.323 (2)	C10—C11	1.397 (3)
N1—C1	1.367 (2)	C11—C12	1.371 (3)
N2—C10	1.344 (2)	C11—H11A	0.9500
N2—C18	1.380 (2)	C12—C13	1.410 (3)
N2—H2N	0.910	C12—H12A	0.9500
C1—C2	1.413 (3)	C13—C14	1.405 (2)
C1—C6	1.425 (2)	C13—C18	1.416 (3)
C2—C3	1.364 (3)	C14—C15	1.370 (3)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.416 (3)	C15—C16	1.410 (3)
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.366 (3)	C16—C17	1.372 (3)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.418 (3)	C17—C18	1.400 (2)
C5—H5A	0.9500	C17—H17A	0.9500
C6—C7	1.405 (3)	N3—O2'	1.239 (5)
C7—C8	1.364 (3)	N3—O3	1.245 (2)
C7—H7A	0.9500	N3—O1	1.247 (2)
C8—C9	1.413 (2)	N3—O1'	1.253 (5)
C8—H8A	0.9500	N3—O3'	1.263 (5)
C9—C10	1.483 (2)	N3—O2	1.263 (2)

N1···C18ⁱ	3.606 (3)	C6···C14ⁱ	3.550 (4)
N1···C10ⁱⁱ	3.388 (3)	C18···C6ⁱⁱ	3.330 (3)
C1···C13ⁱ	3.345 (4)

C9—N1—C1	118.36 (15)	N2—C10—C9	116.81 (15)
C10—N2—C18	123.64 (15)	C11—C10—C9	124.27 (16)
C10—N2—H2N	120.8	C12—C11—C10	120.19 (17)
C18—N2—H2N	115.4	C12—C11—H11A	119.9
N1—C1—C2	118.83 (16)	C10—C11—H11A	119.9
N1—C1—C6	121.75 (16)	C11—C12—C13	120.75 (17)
C2—C1—C6	119.42 (16)	C11—C12—H12A	119.6
C3—C2—C1	120.24 (17)	C13—C12—H12A	119.6
C3—C2—H2A	119.9	C14—C13—C12	123.24 (17)
C1—C2—H2A	119.9	C14—C13—C18	118.36 (17)
C2—C3—C4	120.60 (19)	C12—C13—C18	118.40 (16)
C2—C3—H3A	119.7	C15—C14—C13	120.20 (17)
C4—C3—H3A	119.7	C15—C14—H14A	119.9
C5—C4—C3	120.51 (18)	C13—C14—H14A	119.9
C5—C4—H4A	119.7	C14—C15—C16	120.56 (17)
C3—C4—H4A	119.7	C14—C15—H15A	119.7
C4—C5—C6	120.33 (17)	C16—C15—H15A	119.7
C4—C5—H5A	119.8	C17—C16—C15	120.89 (18)
C6—C5—H5A	119.8	C17—C16—H16A	119.6
C7—C6—C5	123.57 (17)	C15—C16—H16A	119.6
C7—C6—C1	117.54 (16)	C16—C17—C18	118.69 (17)
C5—C6—C1	118.88 (17)	C16—C17—H17A	120.7
C8—C7—C6	120.34 (17)	C18—C17—H17A	120.7
C8—C7—H7A	119.8	N2—C18—C17	120.62 (16)
C6—C7—H7A	119.8	N2—C18—C13	118.09 (16)
C7—C8—C9	118.43 (17)	C17—C18—C13	121.29 (16)
C7—C8—H8A	120.8	O3—N3—O1	122.3 (2)
C9—C8—H8A	120.8	O2'—N3—O1'	128.7 (14)
N1—C9—C8	123.57 (16)	O2'—N3—O3'	118.7 (14)
N1—C9—C10	115.67 (15)	O1'—N3—O3'	107.1 (13)
C8—C9—C10	120.77 (16)	O3—N3—O2	119.2 (2)
N2—C10—C11	118.92 (16)	O1—N3—O2	118.5 (2)

C9—N1—C1—C2	−178.56 (16)	N1—C9—C10—N2	−4.2 (2)
C9—N1—C1—C6	0.9 (2)	C8—C9—C10—N2	176.18 (15)
N1—C1—C2—C3	178.55 (17)	N1—C9—C10—C11	175.52 (16)
C6—C1—C2—C3	−1.0 (3)	C8—C9—C10—C11	−4.1 (3)
C1—C2—C3—C4	0.3 (3)	N2—C10—C11—C12	0.2 (3)
C2—C3—C4—C5	1.1 (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—C14	179.46 (17)
C4—C5—C6—C1	1.0 (3)	C11—C12—C13—C18	0.2 (3)
N1—C1—C6—C7	−0.3 (3)	C12—C13—C14—C15	−179.80 (17)
C2—C1—C6—C7	179.14 (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—C5	0.3 (3)	C14—C15—C16—C17	0.9 (3)
C5—C6—C7—C8	177.74 (17)	C15—C16—C17—C18	0.1 (3)
C1—C6—C7—C8	−1.0 (3)	C10—N2—C18—C17	178.81 (15)
C6—C7—C8—C9	1.7 (3)	C10—N2—C18—C13	−0.6 (2)
C1—N1—C9—C8	−0.2 (2)	C16—C17—C18—N2	179.18 (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—C10	178.41 (16)	C12—C13—C18—N2	0.3 (2)
C18—N2—C10—C11	0.4 (2)	C14—C13—C18—C17	1.6 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.91	1.92	2.766 (2)	153

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃N₂⁺·NO₃⁻
M_r	319.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	6.9756 (6), 10.6408 (9), 19.1226 (15)
β (°)	94.399 (2)
V (Å³)	1415.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15078, 3739, 2115
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.136, 0.97
No. of reflections	3739
No. of parameters	229
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.29

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.91	1.92	2.766 (2)	153

Acknowledgements

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

References

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