In the title compound, C19H13N3O, the dihedral angle between the two quinoline systems is 11.54 (3)°. The mol­ecular conformation is stabilized by intra­molecular N—H⋯N and C—H⋯O hydrogen bonds, with N—H⋯N being bifurcated towards the two N atoms of the two quinoline rings. In the crystal, there are weak intermolecular π–π inter­actions present involving the quinoline rings [centroid–centroid distance 3.7351 (14) Å]

Li, Yanfeng

Shen, Xiaoping

Zhou, Hongbo

English

PubMed

In the title compound, C19H13N3O, the dihedral angle between the two quinoline systems is 11.54&amp;#8197;(3)&amp;#176;. The molecular conformation is stabilized by intramolecular N&amp;#8212;H...N and C&amp;#8212;H...O hydrogen bonds, with N&amp;#8212;H...N being bifurcated towards the two N atoms of the two quinoline rings. In the crystal, there are weak intermolecular &amp;#960;&amp;#8211;&amp;#960; interactions present involving the quinoline rings [centroid&amp;#8211;centroid distance 3.7351&amp;#8197;(14)&amp;#8197;&amp;#197;]

Yanfeng Li

Hongbo Zhou

Xiaoping Shen

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Acta Crystallographica Section E Structure Reports Online

N-(Quinolin-8-yl)quinoline-2-carboxamide

In the title compound, C19H13N3O, the dihedral angle between the two quinoline systems is 11.54 (3)°. The molecular conformation is stabilized by intramolecular N—H...N and C—H...O hydrogen bonds, with N—H...N being bifurcated towards the two N atoms of the two quinoline rings. In the crystal, there are weak intermolecular π–π interactions present involving the quinoline rings [centroid–centroid distance 3.7351 (14) Å].</jats:p

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N-(Quinolin-8-yl)quinoline-2-carbox-amideYanfeng Li, Hongbo Zhou and Xiaoping Shen*School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang212013, People’s Republic of ChinaCorrespondence e-mail: xiaopingshen@163.comReceived 28 April 2012; accepted 4 May 2012Key indicators: single-crystal X-ray study; T = 173 K; mean (C–C) = 0.003 A˚;R factor = 0.035; wR factor = 0.082; data-to-parameter ratio = 7.5.In the title compound, C19H13N3O, the dihedral angle betweenthe two quinoline systems is 11.54 (3). The molecularconformation is stabilized by intramolecular N—H  N andC—H  O hydrogen bonds, with N—H  N being bifurcatedtowards the two N atoms of the two quinoline rings. In thecrystal, there are weak intermolecular – interactionspresent involving the quinoline rings [centroid–centroiddistance 3.7351 (14) A˚].Related literatureFor the synthesis of the title compound and related structures,see: Kim et al. (2009). For applications of the title compoundand background to the synthesis, see: Wang et al. (2011).ExperimentalCrystal dataC19H13N3O Mr = 299.32Orthorhombic, P212121a = 6.3651 (13) A˚b = 11.475 (2) A˚c = 19.861 (4) A˚V = 1450.6 (5) A˚3Z = 4Mo K radiation = 0.09 mm1T = 173 K0.25  0.15  0.15 mmData collectionRigaku Saturn 724 CCDdiffractometerAbsorption correction: multi-scan(ABSCOR; Higashi, 1995)Tmin = 0.978, Tmax = 0.9876769 measured reflections1553 independent reflections1442 reflections with I > 2(I)Rint = 0.036RefinementR[F 2 > 2(F 2)] = 0.035wR(F 2) = 0.082S = 1.061553 reflections208 parametersH-atom parameters constrainedmax = 0.10 e A˚3min = 0.13 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AN2—H2A  N1 0.88 2.27 2.693 (2) 109N2—H2A  N3 0.88 2.27 2.684 (2) 109C12—H12  O1 0.95 2.25 2.867 (2) 122Data collection: CrystalClear (Rigaku, 2008); cell refinement:CrystalClear; data reduction: CrystalClear; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:DIAMOND (Brandenburg, 2006); software used to prepare materialfor publication: SHELXTL (Sheldrick, 2008).The authors thank the National Natural Science Foundationof China for financial support (grant No. 51072071).Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: ZL2476).ReferencesBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.Kim II, J., Kwak, H. Y., Yoon, J. H., Ryu, D. W., Yoo, I. Y., Yang, N., Cho, B. K.,Park, J. G., Lee, H. & Hong, C. S. (2009). Inorg. Chem. 48, 2956–2966.Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Wang, S., Ding, X. H., Zuo, J. L., You, X. Z. & Huang, W. (2011). Coord. Chem.Rev. 256, 1713–1732.organic compoundso1688 Li et al. doi:10.1107/S1600536812020144 Acta Cryst. (2012). E68, o1688Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2012). E68, o1688    supporting informationActa Cryst. (2012). E68, o1688    [doi:10.1107/S1600536812020144]N-(Quinolin-8-yl)quinoline-2-carboxamideYanfeng Li, Hongbo Zhou and Xiaoping ShenS1. Comment The title compound (Hqcq) can act as a tridentate ligand, and has been incorporated into the cyanometalate building block [Fe(qcq)(CN)3]- {qcq = 8-(2-quinolinecarboxamido)quinoline anion}, in which the FeIII ion is coordinated by three carbon atoms of cyanide groups and three N-donors from the qcq ligand in a mer-arrangement (Kim et al., 2009). Through replacement of the cyanide ligands the Fe(qcq) fragment can coordinate to transition metal ions to form various polynuclear and one-dimensional structures with fascinating magnetic properties such as single molecular magnets and single-chain magnets (Kim et al., 2009; Wang et al., 2011). Herein, the crystal structure of the tridentate ligand of Hqcq is presented.The molecular structure of the title compound is shown in Fig. 1. The quinoline rings are essentially planar, with a maximum deviation of 0.046 (1) Å for atom C8 in the (N1/C1-C9) ring and 0.016 (1) Å for atom C14 in the (N3/C11-C19) ring. The dihedral angle between the two quinoline rings is 11.54 (3)°. The amide (N2/C10/O1) plane forms dihedral angles of 14.1 (1)° and 4.2 (1)° with the quinoline rings of (N1/C1-C9) and (N3/C11-C19), respectively. The bond lengths of the title molecule are slightly different from those reported for [Fe(qcq)(CN)3]- (Kim et al., 2009), probably owing to the coordination effect to the tridentate ligand. There are intramolecular hydrogen-bonding interactions between the amido N atom and the N atoms of the quinoline rings, and between the O atom of amide group and the C atom of the quinoline ring. The amido N atom (N2) forms bifurcated hydrogen bonds towards the two N atoms (N1, N3) of the two quinoline rings (Table 1).In the crystal structure, no significant intermolecular hydrogen bonds are observed. The crystal structure features intermolecular π-π interactions between different types of quinoline rings with a distance of ca. 3.735 Å between the centroids of the respective rings (Fig. 2), and the adjacent rings tilted against each other.S2. Experimental The compound of 8-(2-quinolinecarboxamido)quinoline (Hqcq) was preparecd according to a literature method (Kim et al., 2009). Then, 0.3 mmol of Hqcq was added to MeCN (20 mL) with stirring. The resulting solution was filtered and the filtrate was left for slow evaporation in the dark at room temperature. Yellow block-shaped crystals of the title compound suitable for single-crystal X-ray diffraction were obtained after two weeks. Melting point = 429.6-430.5 K. IR (KBr, cm-1): 3314(s), 3044(m), 1678(vs), 1523(vs), 1488(s), 1427(s), 1325(s), 1126(m), 913(s), 834(s), 764(vs), 611(m), 588(m).S3. Refinement All non-H atoms were refined with anisotropic thermal parameters. The C- and N-bound H atoms were calculated in idealized positions and included in the refinement in a riding mode (C-H = 0.95 Å, N-H = 0.88 Å) with Uiso for H assigned as 1.2 times Ueq of the attached atoms. In the absence of atoms heavier than Si and with Mo Kα radiation used supporting informationsup-2Acta Cryst. (2012). E68, o1688    Friedel-pair reflections have been merged (using a MERG 3 command) during the refinement. Assignment of the absolute structure is arbitrary.Figure 1ORTEP diagram of the title compound with displacement ellipsoids drawn at the 30% probability level. Figure 2The crystal packing diagram of the title compound showing the intermolecular π-π interactions.The distances shown are between the centroids of the respective rings, and the symmetry operator codes for generating adjacent aromatic rings are -1+x, y, z and 1+x, y, z. N-(Quinolin-8-yl)quinoline-2-carboxamide Crystal data C19H13N3OMr = 299.32Orthorhombic, P212121Hall symbol: P2ac2aba = 6.3651 (13) Åb = 11.475 (2) Åc = 19.861 (4) ÅV = 1450.6 (5) Å3Z = 4F(000) = 624Dx = 1.371 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 6054 reflectionsθ = 3.4–29.0°µ = 0.09 mm−1T = 173 KBlock, yellow0.25 × 0.15 × 0.15 mmsupporting informationsup-3Acta Cryst. (2012). E68, o1688    Data collection Rigaku Saturn 724 CCD diffractometerRadiation source: Rotating AnodeGraphite monochromatorφ and ω scansAbsorption correction: multi-scan (ABSCOR; Higashi, 1995)Tmin = 0.978, Tmax = 0.9876769 measured reflections1553 independent reflections1442 reflections with I > 2σ(I)Rint = 0.036θmax = 25.3°, θmin = 3.4°h = −7→6k = −13→13l = −23→18Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.035wR(F2) = 0.082S = 1.061553 reflections208 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.0494P)2] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.10 e Å−3Δρmin = −0.13 e Å−3Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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) x y z Uiso*/UeqO1 −0.0149 (2) 0.41328 (13) 0.73413 (7) 0.0458 (4)N1 −0.1752 (2) 0.46907 (14) 0.56729 (8) 0.0328 (4)C1 −0.3327 (3) 0.44137 (16) 0.52317 (10) 0.0309 (4)N2 0.1160 (2) 0.54135 (14) 0.65635 (8) 0.0336 (4)H2A 0.0898 0.5707 0.6163 0.040*C2 −0.3099 (3) 0.47410 (18) 0.45477 (10) 0.0367 (5)H2 −0.1874 0.5146 0.4407 0.044*N3 0.3570 (3) 0.69181 (14) 0.58750 (8) 0.0385 (4)C3 −0.4630 (3) 0.44780 (19) 0.40896 (10) 0.0405 (5)H3 −0.4453 0.4691 0.3631 0.049*C4 −0.6456 (3) 0.38961 (18) 0.42926 (11) 0.0416 (5)H4 −0.7514 0.3724 0.3970 0.050*C5 −0.6737 (3) 0.35718 (18) 0.49498 (10) 0.0390 (5)H5 −0.7993 0.3187 0.5082 0.047*C6 −0.5164 (3) 0.38082 (16) 0.54318 (10) 0.0324 (5)C7 −0.5302 (3) 0.34377 (17) 0.61049 (10) 0.0364 (5)supporting informationsup-4Acta Cryst. (2012). E68, o1688    H7 −0.6505 0.3024 0.6257 0.044*C8 −0.3693 (3) 0.36763 (17) 0.65394 (10) 0.0358 (5)H8 −0.3739 0.3413 0.6993 0.043*C9 −0.1960 (3) 0.43222 (16) 0.62995 (10) 0.0317 (5)C10 −0.0232 (3) 0.46113 (17) 0.67895 (10) 0.0329 (4)C11 0.2965 (3) 0.58357 (17) 0.68860 (10) 0.0322 (5)C12 0.3571 (3) 0.55062 (19) 0.75238 (9) 0.0362 (5)H12 0.2716 0.4994 0.7781 0.043*C13 0.5465 (3) 0.59343 (19) 0.77909 (10) 0.0409 (6)H13 0.5880 0.5697 0.8229 0.049*C14 0.6721 (3) 0.66767 (18) 0.74419 (10) 0.0388 (5)H14 0.7999 0.6945 0.7635 0.047*C15 0.6127 (3) 0.70472 (17) 0.67950 (10) 0.0341 (5)C16 0.7326 (3) 0.78261 (18) 0.64020 (11) 0.0404 (5)H16 0.8604 0.8134 0.6572 0.049*C17 0.6643 (4) 0.81326 (18) 0.57795 (11) 0.0423 (5)H17 0.7423 0.8667 0.5513 0.051*C18 0.4767 (4) 0.76476 (18) 0.55348 (10) 0.0436 (6)H18 0.4330 0.7860 0.5094 0.052*C19 0.4227 (3) 0.66226 (17) 0.65098 (10) 0.0315 (4)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23O1 0.0481 (9) 0.0504 (9) 0.0389 (9) −0.0030 (8) −0.0031 (8) 0.0133 (7)N1 0.0336 (9) 0.0318 (9) 0.0328 (9) 0.0016 (8) 0.0003 (8) −0.0013 (7)C1 0.0303 (10) 0.0286 (10) 0.0337 (10) 0.0012 (9) 0.0019 (9) −0.0059 (8)N2 0.0334 (9) 0.0372 (9) 0.0301 (8) −0.0003 (8) −0.0032 (8) 0.0028 (7)C2 0.0339 (11) 0.0405 (12) 0.0356 (11) −0.0021 (11) 0.0030 (9) −0.0031 (9)N3 0.0466 (10) 0.0354 (9) 0.0335 (9) −0.0013 (9) −0.0026 (9) 0.0011 (7)C3 0.0426 (12) 0.0425 (12) 0.0366 (11) 0.0039 (11) −0.0025 (10) −0.0047 (10)C4 0.0383 (12) 0.0374 (12) 0.0492 (14) 0.0031 (11) −0.0089 (11) −0.0080 (10)C5 0.0342 (11) 0.0317 (11) 0.0512 (14) −0.0025 (11) −0.0032 (10) −0.0044 (10)C6 0.0317 (11) 0.0257 (10) 0.0397 (11) 0.0023 (9) 0.0021 (9) −0.0040 (8)C7 0.0357 (11) 0.0287 (10) 0.0448 (12) 0.0019 (10) 0.0075 (10) −0.0004 (9)C8 0.0393 (11) 0.0314 (10) 0.0367 (11) 0.0020 (10) 0.0046 (10) 0.0003 (9)C9 0.0343 (11) 0.0276 (10) 0.0332 (11) 0.0046 (9) 0.0032 (9) −0.0015 (8)C10 0.0328 (11) 0.0327 (10) 0.0332 (10) 0.0056 (10) 0.0031 (9) −0.0010 (9)C11 0.0324 (11) 0.0337 (10) 0.0307 (11) 0.0043 (10) −0.0002 (9) −0.0053 (8)C12 0.0385 (11) 0.0417 (12) 0.0283 (10) 0.0031 (11) 0.0018 (10) −0.0015 (9)C13 0.0418 (12) 0.0510 (14) 0.0300 (11) 0.0074 (12) −0.0052 (10) −0.0054 (9)C14 0.0352 (11) 0.0462 (13) 0.0350 (12) 0.0071 (11) −0.0055 (10) −0.0104 (10)C15 0.0360 (11) 0.0332 (10) 0.0330 (10) 0.0030 (10) 0.0024 (9) −0.0092 (9)C16 0.0402 (12) 0.0358 (11) 0.0454 (13) −0.0030 (11) 0.0036 (10) −0.0139 (10)C17 0.0496 (14) 0.0350 (11) 0.0423 (13) −0.0087 (11) 0.0051 (11) −0.0044 (9)C18 0.0563 (14) 0.0372 (12) 0.0374 (11) −0.0050 (12) −0.0009 (11) 0.0031 (9)C19 0.0336 (10) 0.0313 (10) 0.0295 (10) 0.0053 (9) 0.0008 (9) −0.0052 (8)supporting informationsup-5Acta Cryst. (2012). E68, o1688    Geometric parameters (Å, º) O1—C10 1.227 (2) C7—H7 0.9500N1—C9 1.321 (2) C8—C9 1.412 (3)N1—C1 1.369 (2) C8—H8 0.9500C1—C2 1.417 (3) C9—C10 1.505 (3)C1—C6 1.417 (3) C11—C12 1.377 (3)N2—C10 1.354 (3) C11—C19 1.421 (3)N2—C11 1.402 (2) C12—C13 1.406 (3)N2—H2A 0.8800 C12—H12 0.9500C2—C3 1.367 (3) C13—C14 1.358 (3)C2—H2 0.9500 C13—H13 0.9500N3—C18 1.318 (3) C14—C15 1.405 (3)N3—C19 1.371 (2) C14—H14 0.9500C3—C4 1.400 (3) C15—C16 1.411 (3)C3—H3 0.9500 C15—C19 1.421 (3)C4—C5 1.369 (3) C16—C17 1.357 (3)C4—H4 0.9500 C16—H16 0.9500C5—C6 1.412 (3) C17—C18 1.405 (3)C5—H5 0.9500 C17—H17 0.9500C6—C7 1.405 (3) C18—H18 0.9500C7—C8 1.367 (3)C9—N1—C1 117.09 (17) C8—C9—C10 117.92 (17)N1—C1—C2 118.50 (18) O1—C10—N2 124.89 (19)N1—C1—C6 122.59 (17) O1—C10—C9 120.68 (19)C2—C1—C6 118.90 (18) N2—C10—C9 114.42 (16)C10—N2—C11 128.30 (17) C12—C11—N2 123.71 (19)C10—N2—H2A 115.8 C12—C11—C19 120.01 (19)C11—N2—H2A 115.8 N2—C11—C19 116.26 (17)C3—C2—C1 120.5 (2) C11—C12—C13 119.4 (2)C3—C2—H2 119.8 C11—C12—H12 120.3C1—C2—H2 119.8 C13—C12—H12 120.3C18—N3—C19 116.89 (19) C14—C13—C12 122.1 (2)C2—C3—C4 120.37 (19) C14—C13—H13 118.9C2—C3—H3 119.8 C12—C13—H13 118.9C4—C3—H3 119.8 C13—C14—C15 119.8 (2)C5—C4—C3 120.8 (2) C13—C14—H14 120.1C5—C4—H4 119.6 C15—C14—H14 120.1C3—C4—H4 119.6 C14—C15—C16 123.5 (2)C4—C5—C6 120.1 (2) C14—C15—C19 119.3 (2)C4—C5—H5 119.9 C16—C15—C19 117.19 (18)C6—C5—H5 119.9 C17—C16—C15 119.7 (2)C7—C6—C5 122.86 (19) C17—C16—H16 120.2C7—C6—C1 117.81 (18) C15—C16—H16 120.2C5—C6—C1 119.30 (18) C16—C17—C18 119.0 (2)C8—C7—C6 119.55 (19) C16—C17—H17 120.5C8—C7—H7 120.2 C18—C17—H17 120.5supporting informationsup-6Acta Cryst. (2012). E68, o1688    C6—C7—H7 120.2 N3—C18—C17 124.4 (2)C7—C8—C9 118.52 (19) N3—C18—H18 117.8C7—C8—H8 120.7 C17—C18—H18 117.8C9—C8—H8 120.7 N3—C19—C11 117.95 (18)N1—C9—C8 124.35 (19) N3—C19—C15 122.76 (19)N1—C9—C10 117.73 (18) C11—C19—C15 119.28 (18)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AN2—H2A···N1 0.88 2.27 2.693 (2) 109N2—H2A···N3 0.88 2.27 2.684 (2) 109C12—H12···O1 0.95 2.25 2.867 (2) 122

<i>N</i>-(Quinolin-8-yl)quinoline-2-carboxamide

DIAMOND. Crystal Impact GbR,

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) xy z U iso*/Ueq

organic compounds o1688 Li et al. doi:10.1107/S1600536812020144 Acta Cryst.

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N-(Quinolin-8-yl)quinoline-2-carboxamide

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N-(Quinolin-8-yl)quinoline-2-carbox­amide

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N-(Quinolin-8-yl)quinoline-2-carboxamide