The title compound, C17H14N2O, crystallizes as a cis formamide isomer. The isoquinoline and benzene fragments are nearly perpendicular [dihedral angle = 81.79 (18)°], whereas the formamide group is virtually coplanar with the isoquinoline unit [dihedral angle = 1.66 (15)°]. Inter­molecular N—H⋯O hydrogen bonds link mol­ecules into a centrosymmetric dimer

Fu Na Cui

Jun Qi Li

Nunno

Qing Bao Song

Sheldrick

Tovar

Xiao Li Chen

English

PubMed

The title compound, C17H14N2O, crystallizes as a cis formamide isomer. The isoquinoline and benzene fragments are nearly perpendicular [dihedral angle = 81.79&amp;#8197;(18)&amp;#176;], whereas the formamide group is virtually coplanar with the isoquinoline unit [dihedral angle = 1.66&amp;#8197;(15)&amp;#176;]. Intermolecular N&amp;#8212;H...O hydrogen bonds link molecules into a centrosymmetric dimer

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Acta Crystallographica Section E Structure Reports Online

N-[3-(2-Methylphenyl)isoquinolin-1-yl]formamide

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N-[3-(2-Methylphenyl)isoquinolin-1-yl]-formamideFu Na Cui, Jun Qi Li, Xiao Li Chen and Qing Bao Song*The State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology,College of Chemical Engineering and Materials Science, Zhejiang University ofTechnology, Hangzhou 310014, People’s Republic of ChinaCorrespondence e-mail: qbsong@zjut.edu.cnReceived 21 March 2009; accepted 30 March 2009Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.003 Å;R factor = 0.043; wR factor = 0.124; data-to-parameter ratio = 13.2.The title compound, C17H14N2O, crystallizes as a cisformamide isomer. The isoquinoline and benzene fragmentsare nearly perpendicular [dihedral angle = 81.79 (18)],whereas the formamide group is virtually coplanar with theisoquinoline unit [dihedral angle = 1.66 (15)]. IntermolecularN—H  O hydrogen bonds link molecules into a centrosym-metric dimer.Related literatureFor the cytotoxic activity of arylisoquinolines, see: Cho et al.(2002, 2003). For the synthethic procedures relevant to thiswork, see: Nunno et al. (2008); Tovar & Swager (1999); Cho etal. (2002).ExperimentalCrystal dataC17H14N2O Mr = 262.30Triclinic, P1a = 5.3898 (14) Åb = 11.166 (3) Åc = 11.899 (3) Å = 106.139 (3) = 93.128 (3) = 103.800 (3)V = 662.4 (3) Å3Z = 2Mo K radiation = 0.08 mm1T = 296 K0.36  0.23  0.16 mmData collectionBruker SMART CCD area-detectordiffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2000)Tmin = 0.971, Tmax = 0.9874772 measured reflections2399 independent reflections1575 reflections with I > 2(I)Rint = 0.017RefinementR[F 2 > 2(F 2)] = 0.043wR(F 2) = 0.124S = 1.032399 reflections182 parametersH-atom parameters constrainedmax = 0.13 e Å3min = 0.19 e Å3Table 1Hydrogen-bond geometry (Å, ).D—H  A D—H H  A D  A D—H  AN2—H2  O1i 0.86 2.10 2.940 (2) 165Symmetry code: (i) x þ 1;yþ 1;zþ 1.Data collection: SMART (Bruker, 2000); cell refinement: SAINT(Bruker, 2000); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:SHELXTL (Sheldrick, 2008); software used to prepare material forpublication: SHELXTL.This work was supported by the Key Discipline of AppliedChemistry, Zhejiang Province, and the State Key LaboratoryBreeding Base of Green Chemistry-Synthesis Technology,Zhejiang University of Technology, People’s Republic ofChina.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: GK2201).ReferencesBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.Cho, W. J., Kim, E. K., Park, Y., Jeong, E. Y., Kim, T. S., Le, T. N., Kim, D. D. &Lee, E. S. (2002). Bioorg. Med. Chem. 10, 2953–2961.Cho, W. J., Min, S. Y., Le, T. N. & Kim, T. S. (2003). Bioorg. Med. Chem. Lett.13, 4451–4454.Nunno, L. D., Vitale, P. & Scilimati, A. (2008). Tetrahedron, 64, 11198–11204.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Tovar, J. D. & Swager, T. M. (1999). J. Org. Chem. 64, 6499–6505.organic compoundso960 Cui et al. doi:10.1107/S1600536809011714 Acta Cryst. (2009). E65, o960Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2009). E65, o960    supporting informationActa Cryst. (2009). E65, o960    [doi:10.1107/S1600536809011714]N-[3-(2-Methylphenyl)isoquinolin-1-yl]formamideFu Na Cui, Jun Qi Li, Xiao Li Chen and Qing Bao SongS1. Comment Many of the arylisoquinoline derivatives exhibit potent cytotoxic activities against five different human tumor cell lines (Cho et al., 2002, 2003). The title compound, that belongs to arylisoquinolines, has been synthesized to study its cytotoxic activity and its crystal structure is reported here.S2. Experimental A 2.5 M solution of n-BuLi in hexanes (54.5 mmol) was added to a solution of the diisopropylamine (59.9 mmol) in THF (5 ml) at 273 K under nitrogen atmosphere. After 10 min, the solution of 2-methylbenzonitrile (36.4 mmol) in THF (5 ml) was added dropwise and the obtained brown reaction mixture was stirred for 1 h, then adding the DMF (18.2 mmol), the mixture was stirred for 2 h at room temperature (Cho et al., 2002; Nunno et al., 2008; Tovar et al., 1999). The mixture was subsequently concentrated under reduced pressure giving the crude product. The residue was recrystallized from ethanol. Colorless crystals of the title compound were obtained by slow evaporation of the solvent after 2 days at room temperature(Yield: 73%, m.p. 401–403 K).S3. Refinement All H atoms were placed in calculated posistion with C—H = 0.93 - 0.96 Å, and N—H = 0.86Å and refined in the riding mode aproximation with Uiso(H) = 1.2Ueq of the carrier atom.supporting informationsup-2Acta Cryst. (2009). E65, o960    Figure 1View of the molecular structure showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms have been omitted for clarity. Figure 2The molecular packing viewed along the a axis. Hydrogen bonds are shown with dashed lines. H atoms are omitted for clarity. N-[3-(2-Methylphenyl)isoquinolin-1-yl]formamide Crystal data C17H14N2OMr = 262.30Triclinic, P1Hall symbol: -P 1a = 5.3898 (14) Åb = 11.166 (3) Åc = 11.899 (3) Åα = 106.139 (3)°β = 93.128 (3)°γ = 103.800 (3)°V = 662.4 (3) Å3Z = 2F(000) = 276Dx = 1.315 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 1222 reflectionsθ = 3.0–26.0°µ = 0.08 mm−1T = 296 KBlock, colourless0.36 × 0.23 × 0.16 mmsupporting informationsup-3Acta Cryst. (2009). E65, o960    Data collection Bruker SMART CCD area-detector diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorDetector resolution: 0 pixels mm-1φ and ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2000)Tmin = 0.971, Tmax = 0.9874772 measured reflections2399 independent reflections1575 reflections with I > 2σ(I)Rint = 0.017θmax = 25.5°, θmin = 3.0°h = −6→6k = −13→13l = −14→14Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.043wR(F2) = 0.124S = 1.032399 reflections182 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) + (0.0578P)2 + 0.0805P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.13 e Å−3Δρmin = −0.19 e Å−3Special details 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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) x y z Uiso*/UeqC1 0.2507 (3) 0.67650 (17) 0.71903 (14) 0.0446 (4)C2 0.1010 (3) 0.74496 (17) 0.67117 (15) 0.0444 (4)C4 −0.0799 (4) 0.8081 (2) 0.51425 (18) 0.0651 (6)H4 −0.1015 0.8032 0.4349 0.078*C5 −0.1976 (4) 0.8866 (2) 0.59439 (18) 0.0627 (6)H5 −0.2959 0.9339 0.5681 0.075*C6 −0.1697 (4) 0.8945 (2) 0.71022 (18) 0.0592 (5)H6 −0.2504 0.9465 0.7627 0.071*C7 −0.0188 (3) 0.82420 (18) 0.75214 (15) 0.0481 (5)C8 0.0201 (4) 0.83123 (19) 0.87248 (16) 0.0550 (5)H8 −0.0586 0.8820 0.9272 0.066*C9 0.1717 (4) 0.76428 (18) 0.90878 (15) 0.0485 (5)C10 0.5217 (4) 0.52789 (19) 0.67853 (16) 0.0551 (5)H10 0.5431 0.5346 0.7583 0.066*supporting informationsup-4Acta Cryst. (2009). E65, o960    C11 0.2307 (4) 0.77304 (19) 1.03607 (15) 0.0479 (5)C12 0.0620 (4) 0.69894 (19) 1.09041 (16) 0.0531 (5)C13 0.1360 (4) 0.7069 (2) 1.20679 (17) 0.0623 (6)H13 0.0261 0.6567 1.2437 0.075*C14 0.3655 (4) 0.7863 (2) 1.26835 (18) 0.0636 (6)H14 0.4105 0.7889 1.3457 0.076*C15 0.5290 (4) 0.8620 (2) 1.21612 (18) 0.0662 (6)H15 0.6831 0.9178 1.2584 0.079*C16 0.4630 (4) 0.8548 (2) 1.09957 (17) 0.0600 (6)H16 0.5751 0.9051 1.0635 0.072*C17 −0.1907 (4) 0.6097 (2) 1.0258 (2) 0.0735 (6)H17A −0.3010 0.6596 1.0076 0.110*H17B −0.2710 0.5602 1.0746 0.110*H17C −0.1617 0.5524 0.9541 0.110*C18 0.0666 (4) 0.7385 (2) 0.55094 (16) 0.0558 (5)H18 0.1441 0.6866 0.4966 0.067*N1 0.2872 (3) 0.68582 (15) 0.83158 (12) 0.0492 (4)N2 0.3716 (3) 0.59354 (15) 0.64362 (12) 0.0517 (4)H2 0.3469 0.5844 0.5694 0.062*O1 0.6325 (3) 0.45974 (14) 0.61283 (11) 0.0655 (4)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23C1 0.0521 (11) 0.0470 (11) 0.0386 (10) 0.0214 (9) 0.0112 (8) 0.0112 (8)C2 0.0477 (10) 0.0478 (11) 0.0410 (10) 0.0187 (9) 0.0078 (8) 0.0134 (8)C4 0.0777 (15) 0.0831 (16) 0.0477 (11) 0.0425 (13) 0.0049 (10) 0.0231 (11)C5 0.0683 (13) 0.0731 (15) 0.0596 (12) 0.0387 (12) 0.0033 (10) 0.0241 (11)C6 0.0639 (13) 0.0663 (14) 0.0569 (12) 0.0364 (11) 0.0094 (10) 0.0168 (10)C7 0.0492 (11) 0.0519 (12) 0.0466 (10) 0.0206 (9) 0.0068 (8) 0.0142 (9)C8 0.0668 (13) 0.0630 (13) 0.0426 (10) 0.0340 (11) 0.0147 (9) 0.0119 (9)C9 0.0555 (11) 0.0555 (12) 0.0384 (10) 0.0238 (10) 0.0114 (8) 0.0116 (9)C10 0.0755 (14) 0.0638 (13) 0.0380 (10) 0.0378 (12) 0.0107 (9) 0.0170 (9)C11 0.0579 (12) 0.0535 (11) 0.0383 (9) 0.0285 (10) 0.0111 (9) 0.0104 (9)C12 0.0595 (12) 0.0560 (12) 0.0463 (11) 0.0227 (10) 0.0070 (9) 0.0132 (9)C13 0.0754 (15) 0.0728 (15) 0.0434 (11) 0.0228 (12) 0.0084 (10) 0.0220 (10)C14 0.0760 (15) 0.0762 (15) 0.0417 (11) 0.0293 (13) 0.0017 (11) 0.0157 (11)C15 0.0628 (13) 0.0766 (15) 0.0529 (12) 0.0210 (12) −0.0034 (10) 0.0094 (11)C16 0.0576 (13) 0.0731 (14) 0.0484 (11) 0.0181 (11) 0.0083 (10) 0.0159 (10)C17 0.0690 (14) 0.0802 (16) 0.0671 (14) 0.0124 (13) −0.0022 (11) 0.0239 (12)C18 0.0651 (13) 0.0687 (14) 0.0419 (10) 0.0332 (11) 0.0089 (9) 0.0163 (10)N1 0.0622 (10) 0.0564 (10) 0.0363 (8) 0.0285 (8) 0.0113 (7) 0.0140 (7)N2 0.0707 (11) 0.0640 (10) 0.0326 (8) 0.0390 (9) 0.0089 (7) 0.0153 (7)O1 0.0930 (11) 0.0775 (10) 0.0454 (7) 0.0555 (9) 0.0183 (7) 0.0194 (7)supporting informationsup-5Acta Cryst. (2009). E65, o960    Geometric parameters (Å, º) C1—N1 1.314 (2) C10—N2 1.334 (2)C1—N2 1.406 (2) C10—H10 0.9300C1—C2 1.430 (2) C11—C12 1.390 (3)C2—C18 1.412 (2) C11—C16 1.393 (3)C2—C7 1.412 (2) C12—C13 1.393 (3)C4—C18 1.365 (3) C12—C17 1.500 (3)C4—C5 1.395 (3) C13—C14 1.367 (3)C4—H4 0.9300 C13—H13 0.9300C5—C6 1.354 (3) C14—C15 1.368 (3)C5—H5 0.9300 C14—H14 0.9300C6—C7 1.416 (3) C15—C16 1.388 (3)C6—H6 0.9300 C15—H15 0.9300C7—C8 1.413 (2) C16—H16 0.9300C8—C9 1.358 (3) C17—H17A 0.9600C8—H8 0.9300 C17—H17B 0.9600C9—N1 1.369 (2) C17—H17C 0.9600C9—C11 1.502 (2) C18—H18 0.9300C10—O1 1.218 (2) N2—H2 0.8600N1—C1—N2 116.00 (15) C16—C11—C9 118.94 (17)N1—C1—C2 124.34 (16) C11—C12—C13 118.20 (19)N2—C1—C2 119.66 (15) C11—C12—C17 121.62 (17)C18—C2—C7 118.91 (16) C13—C12—C17 120.16 (19)C18—C2—C1 124.80 (16) C14—C13—C12 121.9 (2)C7—C2—C1 116.28 (15) C14—C13—H13 119.0C18—C4—C5 120.80 (19) C12—C13—H13 119.0C18—C4—H4 119.6 C13—C14—C15 120.03 (19)C5—C4—H4 119.6 C13—C14—H14 120.0C6—C5—C4 120.51 (18) C15—C14—H14 120.0C6—C5—H5 119.7 C14—C15—C16 119.5 (2)C4—C5—H5 119.7 C14—C15—H15 120.2C5—C6—C7 120.56 (18) C16—C15—H15 120.2C5—C6—H6 119.7 C15—C16—C11 120.7 (2)C7—C6—H6 119.7 C15—C16—H16 119.7C2—C7—C8 118.35 (16) C11—C16—H16 119.7C2—C7—C6 119.00 (16) C12—C17—H17A 109.5C8—C7—C6 122.64 (17) C12—C17—H17B 109.5C9—C8—C7 120.43 (17) H17A—C17—H17B 109.5C9—C8—H8 119.8 C12—C17—H17C 109.5C7—C8—H8 119.8 H17A—C17—H17C 109.5C8—C9—N1 122.13 (16) H17B—C17—H17C 109.5C8—C9—C11 122.85 (16) C4—C18—C2 120.22 (18)N1—C9—C11 115.00 (15) C4—C18—H18 119.9O1—C10—N2 124.36 (17) C2—C18—H18 119.9O1—C10—H10 117.8 C1—N1—C9 118.43 (15)N2—C10—H10 117.8 C10—N2—C1 124.96 (15)supporting informationsup-6Acta Cryst. (2009). E65, o960    C12—C11—C16 119.63 (17) C10—N2—H2 117.5C12—C11—C9 121.41 (17) C1—N2—H2 117.5N1—C1—C2—C18 178.11 (18) C9—C11—C12—C13 176.52 (17)N2—C1—C2—C18 −1.4 (3) C16—C11—C12—C17 179.84 (18)N1—C1—C2—C7 −1.8 (3) C9—C11—C12—C17 −1.9 (3)N2—C1—C2—C7 178.68 (16) C11—C12—C13—C14 1.1 (3)C18—C4—C5—C6 −0.4 (3) C17—C12—C13—C14 179.6 (2)C4—C5—C6—C7 0.6 (3) C12—C13—C14—C15 0.6 (3)C18—C2—C7—C8 −179.13 (18) C13—C14—C15—C16 −1.7 (3)C1—C2—C7—C8 0.8 (3) C14—C15—C16—C11 1.0 (3)C18—C2—C7—C6 0.1 (3) C12—C11—C16—C15 0.7 (3)C1—C2—C7—C6 −179.99 (17) C9—C11—C16—C15 −177.58 (18)C5—C6—C7—C2 −0.4 (3) C5—C4—C18—C2 0.0 (3)C5—C6—C7—C8 178.7 (2) C7—C2—C18—C4 0.1 (3)C2—C7—C8—C9 0.8 (3) C1—C2—C18—C4 −179.81 (19)C6—C7—C8—C9 −178.41 (19) N2—C1—N1—C9 −179.35 (16)C7—C8—C9—N1 −1.5 (3) C2—C1—N1—C9 1.1 (3)C7—C8—C9—C11 176.90 (18) C8—C9—N1—C1 0.6 (3)C8—C9—C11—C12 83.5 (3) C11—C9—N1—C1 −177.95 (17)N1—C9—C11—C12 −98.0 (2) O1—C10—N2—C1 −177.35 (19)C8—C9—C11—C16 −98.3 (2) N1—C1—N2—C10 −1.6 (3)N1—C9—C11—C16 80.3 (2) C2—C1—N2—C10 177.92 (17)C16—C11—C12—C13 −1.7 (3)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AN2—H2···O1i 0.86 2.10 2.940 (2) 165Symmetry code: (i) −x+1, −y+1, −z+1.

-[3-(2-Methylphenyl)isoquinolin-1-yl]formamide

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueq

organic compounds o960 Cui et al. doi:10.1107/S1600536809011714 Acta Cryst.

The molecular packing viewed along the a axis. Hydrogen bonds are shown with dashed lines. H atoms are omitted for clarity. N-[3-(2-Methylphenyl)isoquinolin-1-yl]formamide Crystal data

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N-[3-(2-Methyl­phen­yl)isoquinolin-1-yl]formamide

N-[3-(2-Methylphenyl)isoquinolin-1-yl]formamide

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N-[3-(2-Methyl­phen­yl)isoquinolin-1-yl]formamide

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N-[3-(2-Methylphenyl)isoquinolin-1-yl]formamide