112 3-(4-Methylpyridin-2-ylamino)isobenzofuran-1(3H)-one

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112 3-(4-Methylpyridin-2-ylamino)isobenzofuran-1(3H)-one
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  electronic reprint Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 Editors: W. Clegg and D. G. Watson 3-(4-Methylpyridin-2-ylamino)isobenzofuran-1(3 H  )-one Mustafa Odabas¸o ˇglu and Orhan B¨uy¨ukg¨ung  ¨or Copyright © International Union of CrystallographyAuthor(s) of this paper may load this reprint on their own web site provided that this cover page is retained. Republication of this article or itsstorage in electronic databases or the like is not permitted without prior permission in writing from the IUCr. Acta Cryst. (2006). E 62 , o2316–o2317 Odabas¸oˇglu and B¨uy¨ukg¨ung ¨or ¯ C 14 H 12 N 2 O 2  organic papers o2316 Odabas¸og˘lu and Bu¨ yu¨ kgu¨ ngo¨ r  C 14 H 12 N 2 O 2 doi:10.1107/S160053680601717X Acta Cryst. (2006). E 62 , o2316–o2317 Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 3-(4-Methylpyridin-2-ylamino)isobenzo-furan-1(3 H )-one Mustafa Odabas¸og˘lu a * andOrhan Bu¨yu¨kgu¨ngo¨r b a Department of Chemistry, Faculty of Arts &Science, Ondokuz Mayıs University, TR-55139Kurupelit Samsun, Turkey, and b Department of Physics, Faculty of Arts & Science, OndokuzMayıs University, TR-55139 Kurupelit Samsun,TurkeyCorrespondence e-mail: muodabas@omu.edu.tr Key indicators Single-crystal X-ray study T  = 296 KMean   (C–C) = 0.006 A˚ R factor = 0.079 wR factor = 0.237Data-to-parameter ratio = 15.0For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e.Received 8 May 2006Accepted 9 May 20063-Substituted phthalides,Part VII # 2006 International Union of CrystallographyAll rights reserved Crystals of the title compound, C 14 H 12 O 2 N 2 , are stabilized byinversion-related N—H ÁÁÁ N and C—H ÁÁÁ O intermolecularhydrogen bonds and also by two C—H ÁÁÁ  interactions. TheN—H ÁÁÁ N and C—H ÁÁÁ O hydrogen bonds generate R 22 (8) and R 22 (10) ring motifs, respectively, and the phthalide section of the molecule is planar. The dihedral angle between thephthalide group and the pyridyl ring is 82.06 (17)  . Comment In separate papers, we have reported the syntheses and crystalstructures of 3-(2-pyridylamino)phthalide (Odabas¸og ˘lu &Bu ¨   y u ¨ kgu ¨ ngo ¨ r, 2006 a ) and 3-(3-pyridylamino)phthalide(Odabas¸og ˘lu & Bu ¨   y u ¨ kgu ¨ ngo ¨ r, 2006 b ). We report here thestructure of 3-(4-methylpyridin-2-ylamino)isobenzofuran-1(3 H  )-one (Fig. 1 and Table 1).The phthalide group (C1–C8/O2) is planar, the largestdeviation from the mean plane being 0.040 (4) A˚for atom C8.The dihedral angle between the mean planes of the phthalidegroup and the pyridyl ring is 82.06 (17)  .The crystal packing is stabilized by inversion-related N1—H1 ÁÁÁ N2 i and C8—H8 ÁÁÁ O1 ii intermolecular hydrogen bonds, Figure 1 A view of (I), showing the atomic numbering scheme, with displacementellipsoids drawn at the 40% probability level. electronic reprint  which generate centrosymmetric R 22 (8) and R 22 (10) ring motifs,respectively (Etter, 1990), and C—H ÁÁÁ  interactions (Fig. 2and Table 2). Experimental The title compound was prepared as described by Odabas¸og ˘lu &Bu ¨   y u ¨ kgu ¨ ngo ¨ r (2006 c ), using phthalaldehydic acid and 2-amino-4-methylpyridine as starting materials (yield 92%, m.p. 435–437 K).Crystals of (I) suitable for X-ray analysis were obtained by slowevaporation of an ethanol (95%) solution at room temperature. Crystal data C 14 H 12 N 2 O 2 M  r  = 240.26Triclinic, P 1 a = 7.6621 (18) A˚ b = 8.0381 (18) A˚ c = 10.616 (2) A˚  = 87.387 (17)   = 78.177 (18)    = 78.456 (18)  V  = 627.0 (2) A˚ 3 Z  = 2 D  x = 1.273 Mg m À 3 Mo K   radiation  = 0.09 mm À 1 T  = 296 KPrism, colorless0.47 Â 0.36 Â 0.17 mm Data collection Stoe IPDS-2 diffractometer ! scansAbsorption correction: integration(  X-RED32 ; Stoe & Cie, 2002) T  min = 0.960, T  max = 0.9875736 measured reflections2454 independent reflections1575 reflections with I  > 2   (  I  ) R int = 0.079   max = 26.0  Refinement  Refinement on F  2 R [ F  2 > 2   ( F  2 )] = 0.080 wR ( F  2 ) = 0.237 S = 1.092454 reflections164 parametersH-atom parameters constrained w = 1/[   2 ( F  o2 ) + (0.0967 P ) 2 + 0.443 P ]where P = ( F  o2 + 2 F  c2 )/3( Á /   ) max < 0.001 Á  max = 0.52 e A˚ À 3 Á  min = À 0.31 e A˚ À 3 Table 1 Selected geometric parameters (A˚,  ). C1—O1 1.209 (5)C1—O2 1.369 (5)C2—C7 1.381 (5)C7—C8 1.517 (5)C8—N1 1.403 (5)C9—N1 1.406 (5)O1—C1—O2 121.5 (3)O1—C1—C2 130.5 (4)N1—C8—O2 111.0 (3) Table 2 Hydrogen-bond geometry (A˚,  ). D —H ÁÁÁ  A D —H H ÁÁÁ  A D ÁÁÁ  A D —H ÁÁÁ  A N1—H1 ÁÁÁ N2 i 0.86 2.31 3.075 (5) 149C8—H8 ÁÁÁ O1 ii 0.98 2.43 3.211 (6) 136C6—H6 ÁÁÁ Cg 1 iii 0.93 3.37 4.039 (4) 131C13—H13 ÁÁÁ Cg 2 i 0.93 2.82 3.702 (5) 160 Symmetry codes: (i) À  x þ 1 ; À  y þ 1 ; À z þ 1; (ii) À  x þ 1 ; À  y þ 1 ; À z ; (iii) x ;  y þ 1 ; z . Cg 1 and Cg 2 are the centroids of the C9–C13 and C2–C7 rings, respectively. All H atoms were refined using the riding-model approximation,with C—H = 0.93 A˚for aromatic, 0.98 A˚for methine and N—H =0.86 A˚for amino H atoms, with U  iso (H) = 1.2 U  eq (parent atom), andC—H = 0.96 A˚for methyl H atoms with U  iso (H) = 1.5 U  eq (C).Data collection: X-AREA (Stoe & Cie, 2002); cell refinement:  X-AREA ; data reduction: X-RED32 (Stoe & Cie, 2002); program(s)used to solve structure: SHELXS97  (Sheldrick, 1990); program(s)used to refine structure: SHELXL97  (Sheldrick, 1997); moleculargraphics: ORTEP-3 for Windows (Farrugia, 1997); software used toprepare material for publication: WinGX  (Farrugia, 1999). The authors acknowledge the Faculty of Arts and Sciences,Ondokuz Mayıs University, Turkey, for the use of the Stoe  IPDS II diffractometer (purchased under grant F.279 of theUniversity Research Fund). References Etter, M. C. (1990). Acc. Chem. Res. 23 , 120–126.Farrugia, L. J. (1997). J. Appl. Cryst. 30 , 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32 , 837–838.Odabas¸og ˘lu, M. & Bu ¨ yu ¨ kgu ¨ ngo ¨ r, O. (2006 a ). Acta Cryst. E 62 , o2079–o2080.Odabas¸og ˘lu, M. & Bu ¨ yu ¨ kgu ¨ ngo ¨ r, O. (2006 b ). Acta Cryst. E 62 , o2088–o2089.Odabas¸og ˘lu, M. & Bu ¨ yu ¨ kgu ¨ ngo ¨ r, O. (2006 c ). Acta Cryst. E 62 , o1879–o1881.Sheldrick, G. M. (1990). Acta Cryst. A 46 , 467–473.Sheldrick, G. M. (1997). SHELXL97  . University of Go ¨ ttingen, Germany.Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe& Cie, Darmstadt, Germany. organic papers Acta Cryst. (2006). E 62 , o2316–o2317 Odabas¸og˘lu and Bu¨ yu¨ kgu¨ ngo¨ r  C 14 H 12 N 2 O 2 o2317 Figure 2 A packing diagram for (I), with hydrogen bonds and C—H ÁÁÁ  interactions drawn as dashed lines. H atoms not involved in hydrogenbonding have been omitted. electronic reprint
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