Literature DB >> 21202715

2-(2-Quinol-yl)quinolinium nitrate.

Anita Abedi, Arezoo Bahrami Shabestari, Vahid Amani.   

Abstract

In the cation of the title compound, C(18)H(13)N(2) (+)·NO(3) (-), 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 inter-molecular contacts [C⋯C = 3.330 (3) and 3.345 (4) Å], and link to the anions via N-H⋯O hydrogen bonds.

Entities:  

Year:  2008        PMID： 21202715      PMCID： PMC2961481          DOI： 10.1107/S1600536808012579

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 319.31 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.136 S = 0.97 3739 reflections 229 parameters 3 restraints H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.29 e Å−3 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. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012579/cv2401sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012579/cv2401Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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
Bruker SMART 1000 CCD area-detector diffractometer2115 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 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
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.
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
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)
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)
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.911.922.766 (2)153
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2N⋯O10.911.922.766 (2)153
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