Ranjitha, M.

Shobha Jagannath

University of Mysore - Digital Repository of Research, Innovation and Scholarship (ePrints@UoM)

Crystal structure of cis-1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-oneP. S. Pradeep,a S. Naveen,b M. N. Kumara,cK. M. Mahadevana and N. K. Lokanathd*aDepartment of Chemistry, Kuvempu University, Jnanasahyadri, Shankaraghatta577 451, India, bInstitution of Excellence, University of Mysore, Manasagangotri,Mysore 570 006, India, cDepartment of Chemistry, Yuvaraja’s College, University ofMysore, Mysore 570 005, India, and dDepartment of Studies in Physics, University ofMysore, Manasagangotri, Mysore 570 006, India. *Correspondence e-mail:lokanath@physics.uni-mysore.ac.inReceived 24 July 2014; accepted 2 August 2014Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), ChinaIn the title compound, C16H22N2O, the azepan-2-one ringadopts a chair conformation, while the 1,2,3,4-tetrahydro-pyridine ring adopts a half-chair conformation. In the crystal,molecules are linked by N—H  O hydrogen bonds, formingsupramolecular chains propagated along [101], with weak C—H  O interactions occurring between the chains.Keywords: crystal structure; tetrahydroquinolines; azepan-2-one;hydrogen bonding.CCDC reference: 10176821. Related literatureFor applications of tetrahydroquinolines, see: Konishi et al.(1990).2. Experimental2.1. Crystal dataC16H22N2OMr = 258.36Monoclinic, P21=na = 9.1640 (17) A˚b = 13.1687 (18) A˚c = 11.988 (2) A˚ = 96.825 (11)V = 1436.4 (4) A˚3Z = 4Cu K radiation = 0.59 mm1T = 296 K0.23  0.22  0.21 mm2.2. Data collectionBruker X8 Proteum diffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2013)Tmin = 0.874, Tmax = 0.8847903 measured reflections2343 independent reflections2106 reflections with I > 2(I)Rint = 0.0282.3. RefinementR[F 2 > 2(F 2)] = 0.049wR(F 2) = 0.139S = 1.062343 reflections173 parametersH-atom parameters constrainedmax = 0.34 e A˚3min = 0.36 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AN1—H1  O19i 0.86 2.40 2.988 (2) 126C14—H14A  O19ii 0.97 2.57 3.320 (2) 134Symmetry codes: (i) x þ 12;yþ 32; z 12; (ii) x þ 12; yþ 12;zþ 12.Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT(Bruker, 2013); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:Mercury (Macrae et al., 2008); software used to prepare material forpublication: Mercury.AcknowledgementsThe authors are thankful to IOE, Vijnana Bhavana, Universityof Mysore, Mysore, for providing the single-crystal X-raydiffractometer facility.data reportsActa Cryst. (2014). E70, o981–o982 doi:10.1107/S1600536814017826 Pradeep et al. o981ISSN 1600-5368Supporting information for this paper is available from the IUCrelectronic archives (Reference: XU5808).ReferencesBruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.Konishi, M., Ohkuma, H., Tsuno, T. & Oki, T. (1990). J. Am. Chem. Soc. 112,3715–3716.Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P.,Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood,P. A. (2008). J. Appl. Cryst. 41, 466–470.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.data reportso982 Pradeep et al.  C16H22N2O Acta Cryst. (2014). E70, o981–o982supporting informationsup-1Acta Cryst. (2014). E70, o981–o982    supporting informationActa Cryst. (2014). E70, o981–o982    [doi:10.1107/S1600536814017826]Crystal structure of cis-1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-oneP. S. Pradeep, S. Naveen, M. N. Kumara, K. M. Mahadevan and N. K. LokanathS1. Comment Tetrahydroquinolines are an important family of heterocyclic compounds having wide range of biological activities which includes antimalarial, antitumoral, antioxidant, etc. In particular 2-Methyl-1,2,3,4-tetrahydroquinoline is present in human brain and a natural antitumor antibiotic, has a complex structure built on the tetrahydroquinoline system (Konishi et al., 1990). Hence, in continuation of our effort to identify new quinoline based therapeutic agents, the title compound has been synthesized and herein we report its crystal structure.The ORTEP of the molecule is shown in figure 1. The title compound is chiral. In the arbitrarily chosen asymmetric molecule, C2 has S configuration whereas C4 has R configuration. The azepan ring lies in the equatorial plane of the fused rings as indicated by the dihedral angle value of 66.28 (8)°. A study of torsion angles, asymmetric parameters and least squares plane calculations reveals that the quinoline ring in the structure adopts a half chair conformation with the atom C3 deviating by 0.3278 (18) Å from the least-squares plane defined by the atoms N1/C2/C3/C4/C5/C10. This is confirmed by the puckering amplitude Q = 0.4857 (18) Å. The structure exhibits weak intermolecular hydrogen bonds of the type C—H···O and N—H···O. The packing of the molecules when viewed along the a axis indicate that they are stacked in pairs.S2. Experimental A catalytic amount of SbF3 (10 mol %) was added to the mixture of aniline(1 equivalent) and N-vinyl caprolactam(2–3 equivalent) in acetonitrile (5–10 ml). The reaction mixture was stirred at ambient temperature (~25 °C) for 20–70 min. The reaction was monitored by TLC by using ethyl acetate/hexane as eluent. After the completion of the reaction, the solvent was removed under vacuo. The crude product was then quenched with water and the catalyst was decomposed by addition of appropriate amount of sodium bicarbonate solution, extracted with ethyl acetate (10 ml × 5 times), dried and was purified by column chromatography using ethyl acetate/hexane as eluent (pet ether/ethyl acetate 80:20 v/v). The white solid crystals were obtained by slow evaporation method by using petroleum ether: ethyl acetate, 8:2 v/v as solvents. M.P. = 155–160 °C. Yield: 93%.S3. Refinement The hydrogen atoms were placed geometrically with N—H = 0.86, C—H = 0.93–0.98 Å, and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C) for the methyl H atoms and 1.2Ueq(N,C) for the others.supporting informationsup-2Acta Cryst. (2014). E70, o981–o982    Figure 1A view of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. supporting informationsup-3Acta Cryst. (2014). E70, o981–o982    Figure 2A viewed along the a axis of the crystal packing of the title compound. 1-(2-Methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one Crystal data C16H22N2OMr = 258.36Monoclinic, P21/nHall symbol: -P 2yna = 9.1640 (17) Åb = 13.1687 (18) Åc = 11.988 (2) Åβ = 96.825 (11)°V = 1436.4 (4) Å3Z = 4F(000) = 560Dx = 1.195 Mg m−3Cu Kα radiation, λ = 1.54178 ÅCell parameters from 2343 reflectionsθ = 6.7–64.8°µ = 0.59 mm−1T = 296 KBlock, colorless0.23 × 0.22 × 0.21 mmData collection Bruker X8 Proteum diffractometerRadiation source: Bruker MicroStar microfocus rotating anodeHelios multilayer optics monochromatorDetector resolution: 18.4 pixels mm-1φ and ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2013)Tmin = 0.874, Tmax = 0.8847903 measured reflections2343 independent reflectionssupporting informationsup-4Acta Cryst. (2014). E70, o981–o982    2106 reflections with I > 2σ(I)Rint = 0.028θmax = 64.8°, θmin = 6.7°h = −10→10k = −15→4l = −14→13Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.049wR(F2) = 0.139S = 1.062343 reflections173 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) + (0.0671P)2 + 0.4283P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.34 e Å−3Δρmin = −0.36 e Å−3Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion anglesRefinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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*/UeqO19 0.20029 (15) 0.75502 (10) 0.32245 (11) 0.0661 (5)N1 0.53573 (16) 0.85016 (11) −0.01036 (12) 0.0538 (5)N12 0.28345 (14) 0.90157 (10) 0.25474 (10) 0.0438 (4)C2 0.60480 (18) 0.82217 (14) 0.10008 (15) 0.0511 (6)C3 0.52791 (17) 0.87701 (14) 0.18769 (14) 0.0497 (5)C4 0.36664 (17) 0.84597 (12) 0.17675 (13) 0.0421 (5)C5 0.29631 (17) 0.85491 (12) 0.05626 (13) 0.0439 (5)C6 0.1450 (2) 0.86076 (16) 0.03030 (16) 0.0593 (6)C7 0.0790 (2) 0.86425 (19) −0.07861 (17) 0.0718 (8)C8 0.1649 (3) 0.86264 (17) −0.16454 (16) 0.0700 (7)C9 0.3153 (2) 0.85678 (14) −0.14226 (15) 0.0605 (7)C10 0.38380 (19) 0.85289 (12) −0.03180 (14) 0.0459 (5)C11 0.7676 (2) 0.84612 (19) 0.1097 (2) 0.0743 (8)C13 0.28372 (19) 1.01269 (13) 0.25122 (14) 0.0514 (6)C14 0.3621 (2) 1.06237 (15) 0.35552 (17) 0.0640 (7)C15 0.2718 (3) 1.06735 (17) 0.45383 (18) 0.0770 (8)C16 0.2169 (3) 0.96542 (17) 0.49058 (17) 0.0720 (8)C17 0.1190 (2) 0.90829 (16) 0.40028 (17) 0.0627 (7)C18 0.20364 (18) 0.84820 (14) 0.32180 (13) 0.0486 (6)H1 0.58880 0.86510 −0.06260 0.0640*H2 0.59290 0.74890 0.10990 0.0610*H3A 0.53550 0.94980 0.17750 0.0600*supporting informationsup-5Acta Cryst. (2014). E70, o981–o982    H3B 0.57490 0.86010 0.26220 0.0600*H4 0.36380 0.77400 0.19710 0.0510*H6 0.08640 0.86240 0.08850 0.0710*H7 −0.02280 0.86770 −0.09380 0.0860*H8 0.12120 0.86550 −0.23860 0.0840*H9 0.37220 0.85540 −0.20150 0.0730*H11A 0.81160 0.80920 0.05330 0.1120*H11B 0.81330 0.82670 0.18280 0.1120*H11C 0.78080 0.91760 0.09920 0.1120*H13A 0.18280 1.03640 0.24060 0.0620*H13B 0.33020 1.03440 0.18670 0.0620*H14A 0.38960 1.13080 0.33670 0.0770*H14B 0.45190 1.02500 0.37870 0.0770*H15A 0.33110 1.09830 0.51720 0.0920*H15B 0.18770 1.11120 0.43340 0.0920*H16A 0.16270 0.97610 0.55430 0.0860*H16B 0.30120 0.92320 0.51580 0.0860*H17A 0.05640 0.86230 0.43620 0.0750*H17B 0.05600 0.95660 0.35650 0.0750*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23O19 0.0806 (9) 0.0577 (9) 0.0692 (9) −0.0120 (7) 0.0477 (7) −0.0006 (6)N1 0.0525 (8) 0.0624 (9) 0.0526 (8) 0.0030 (7) 0.0321 (7) 0.0032 (7)N12 0.0447 (7) 0.0501 (8) 0.0406 (7) 0.0023 (6) 0.0221 (6) 0.0023 (6)C2 0.0446 (9) 0.0534 (10) 0.0599 (10) 0.0014 (7) 0.0254 (8) 0.0009 (8)C3 0.0411 (8) 0.0607 (10) 0.0501 (9) −0.0022 (7) 0.0173 (7) −0.0045 (8)C4 0.0419 (8) 0.0472 (9) 0.0412 (8) −0.0003 (7) 0.0212 (6) 0.0003 (7)C5 0.0441 (9) 0.0469 (9) 0.0436 (9) −0.0039 (7) 0.0179 (7) −0.0008 (7)C6 0.0468 (10) 0.0805 (13) 0.0529 (10) −0.0060 (9) 0.0161 (8) 0.0002 (9)C7 0.0567 (11) 0.0964 (16) 0.0609 (12) −0.0073 (11) 0.0017 (9) 0.0001 (11)C8 0.0819 (14) 0.0791 (14) 0.0470 (10) −0.0082 (11) 0.0000 (10) −0.0047 (9)C9 0.0812 (14) 0.0618 (11) 0.0424 (9) −0.0068 (9) 0.0238 (9) −0.0057 (8)C10 0.0555 (9) 0.0415 (9) 0.0448 (9) −0.0023 (7) 0.0227 (7) −0.0012 (7)C11 0.0451 (10) 0.0932 (16) 0.0900 (15) 0.0016 (10) 0.0301 (10) −0.0044 (12)C13 0.0576 (10) 0.0523 (10) 0.0480 (9) 0.0097 (8) 0.0219 (8) 0.0091 (7)C14 0.0803 (13) 0.0496 (11) 0.0641 (12) 0.0029 (9) 0.0170 (10) −0.0019 (9)C15 0.1127 (18) 0.0636 (13) 0.0579 (12) 0.0138 (12) 0.0233 (12) −0.0091 (10)C16 0.0985 (16) 0.0738 (14) 0.0498 (11) 0.0185 (12) 0.0348 (10) −0.0001 (9)C17 0.0607 (11) 0.0735 (13) 0.0616 (11) 0.0111 (9) 0.0388 (9) 0.0080 (10)C18 0.0454 (9) 0.0591 (11) 0.0454 (9) 0.0002 (7) 0.0225 (7) 0.0031 (7)Geometric parameters (Å, º) O19—C18 1.228 (2) C2—H2 0.9800N1—C2 1.446 (2) C3—H3A 0.9700N1—C10 1.386 (2) C3—H3B 0.9700supporting informationsup-6Acta Cryst. (2014). E70, o981–o982    N12—C4 1.470 (2) C4—H4 0.9800N12—C13 1.464 (2) C6—H6 0.9300N12—C18 1.347 (2) C7—H7 0.9300N1—H1 0.8600 C8—H8 0.9300C2—C11 1.516 (3) C9—H9 0.9300C2—C3 1.516 (2) C11—H11A 0.9600C3—C4 1.524 (2) C11—H11B 0.9600C4—C5 1.515 (2) C11—H11C 0.9600C5—C6 1.387 (2) C13—H13A 0.9700C5—C10 1.400 (2) C13—H13B 0.9700C6—C7 1.373 (3) C14—H14A 0.9700C7—C8 1.369 (3) C14—H14B 0.9700C8—C9 1.375 (3) C15—H15A 0.9700C9—C10 1.397 (2) C15—H15B 0.9700C13—C14 1.515 (3) C16—H16A 0.9700C14—C15 1.520 (3) C16—H16B 0.9700C15—C16 1.517 (3) C17—H17A 0.9700C16—C17 1.521 (3) C17—H17B 0.9700C17—C18 1.512 (3)C2—N1—C10 119.82 (14) C5—C4—H4 107.00C4—N12—C13 118.48 (12) C5—C6—H6 119.00C4—N12—C18 118.62 (13) C7—C6—H6 119.00C13—N12—C18 122.79 (14) C6—C7—H7 120.00C2—N1—H1 120.00 C8—C7—H7 120.00C10—N1—H1 120.00 C7—C8—H8 120.00C3—C2—C11 112.49 (16) C9—C8—H8 120.00N1—C2—C3 108.91 (14) C8—C9—H9 120.00N1—C2—C11 109.66 (16) C10—C9—H9 120.00C2—C3—C4 109.79 (14) C2—C11—H11A 109.00N12—C4—C5 111.95 (13) C2—C11—H11B 109.00C3—C4—C5 111.08 (13) C2—C11—H11C 109.00N12—C4—C3 112.50 (13) H11A—C11—H11B 110.00C6—C5—C10 118.62 (15) H11A—C11—H11C 110.00C4—C5—C6 121.27 (15) H11B—C11—H11C 109.00C4—C5—C10 120.05 (14) N12—C13—H13A 109.00C5—C6—C7 122.08 (17) N12—C13—H13B 109.00C6—C7—C8 119.17 (19) C14—C13—H13A 109.00C7—C8—C9 120.51 (18) C14—C13—H13B 109.00C8—C9—C10 120.89 (17) H13A—C13—H13B 108.00N1—C10—C5 120.90 (15) C13—C14—H14A 109.00N1—C10—C9 120.33 (16) C13—C14—H14B 109.00C5—C10—C9 118.75 (16) C15—C14—H14A 109.00N12—C13—C14 114.22 (14) C15—C14—H14B 109.00C13—C14—C15 114.23 (16) H14A—C14—H14B 108.00C14—C15—C16 114.64 (18) C14—C15—H15A 109.00C15—C16—C17 114.77 (18) C14—C15—H15B 109.00C16—C17—C18 113.52 (17) C16—C15—H15A 109.00supporting informationsup-7Acta Cryst. (2014). E70, o981–o982    N12—C18—C17 116.96 (16) C16—C15—H15B 109.00O19—C18—N12 122.76 (16) H15A—C15—H15B 108.00O19—C18—C17 120.27 (16) C15—C16—H16A 109.00N1—C2—H2 109.00 C15—C16—H16B 109.00C3—C2—H2 109.00 C17—C16—H16A 109.00C11—C2—H2 109.00 C17—C16—H16B 109.00C2—C3—H3A 110.00 H16A—C16—H16B 108.00C2—C3—H3B 110.00 C16—C17—H17A 109.00C4—C3—H3A 110.00 C16—C17—H17B 109.00C4—C3—H3B 110.00 C18—C17—H17A 109.00H3A—C3—H3B 108.00 C18—C17—H17B 109.00N12—C4—H4 107.00 H17A—C17—H17B 108.00C3—C4—H4 107.00C10—N1—C2—C3 −44.6 (2) C3—C4—C5—C6 −160.41 (16)C10—N1—C2—C11 −168.08 (16) C3—C4—C5—C10 22.4 (2)C2—N1—C10—C5 16.6 (2) C4—C5—C6—C7 −176.99 (19)C2—N1—C10—C9 −165.36 (16) C10—C5—C6—C7 0.2 (3)C13—N12—C4—C3 56.10 (18) C4—C5—C10—N1 −4.7 (2)C13—N12—C4—C5 −69.81 (17) C4—C5—C10—C9 177.21 (15)C18—N12—C4—C3 −127.62 (15) C6—C5—C10—N1 178.05 (16)C18—N12—C4—C5 106.48 (16) C6—C5—C10—C9 0.0 (2)C4—N12—C13—C14 −113.04 (16) C5—C6—C7—C8 −0.5 (3)C18—N12—C13—C14 70.8 (2) C6—C7—C8—C9 0.5 (3)C4—N12—C18—O19 1.8 (2) C7—C8—C9—C10 −0.3 (3)C4—N12—C18—C17 −179.65 (14) C8—C9—C10—N1 −178.00 (17)C13—N12—C18—O19 177.93 (15) C8—C9—C10—C5 0.1 (3)C13—N12—C18—C17 −3.5 (2) N12—C13—C14—C15 −79.6 (2)N1—C2—C3—C4 60.77 (18) C13—C14—C15—C16 56.7 (3)C11—C2—C3—C4 −177.44 (16) C14—C15—C16—C17 −59.5 (3)C2—C3—C4—N12 −176.30 (13) C15—C16—C17—C18 83.3 (2)C2—C3—C4—C5 −49.92 (18) C16—C17—C18—O19 112.4 (2)N12—C4—C5—C6 −33.7 (2) C16—C17—C18—N12 −66.2 (2)N12—C4—C5—C10 149.10 (14)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AN1—H1···O19i 0.86 2.40 2.988 (2) 126C14—H14A···O19ii 0.97 2.57 3.320 (2) 134Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1/2, y+1/2, −z+1/2.

In vitro micropropagation from leaf and stem derived callus of solanum diphyllum -a potent medicinal herb

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In vitro micropropagation from leaf and stem derived callus of solanum diphyllum -a potent medicinal herb

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