108 3-(2-Methoxyanilino)isobenzofuran-1(3H)-one

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108 3-(2-Methoxyanilino)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-(2-Methoxyanilino)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 , o1884–o1885 Odabas¸oˇglu and B¨uy¨ukg¨ung ¨or ¯ C 15 H 13 NO 3  organic papers o1884 Odabas¸og˘lu and Bu¨ yu¨ kgu¨ ngo¨ r  C 15 H 13 NO 3 doi:10.1107/S1600536806012815 Acta Cryst. (2006). E 62 , o1884–o1885 Acta Crystallographica Section E Structure ReportsOnline ISSN 1600-5368 3-(2-Methoxyanilino)isobenzofuran-1(3 H )-one Mustafa Odabas¸og˘lu a * andOrhan Bu¨yu¨kgu¨ngo¨r b a Department of Chemistry, Faculty of Arts andSciences, Ondokuz Mayıs University, TR-55139Kurupelit Samsun, Turkey, and b Department of Physics, Faculty of Arts and Sciences, 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) = 0.003 A˚ R factor = 0.040 wR factor = 0.100Data-to-parameter ratio = 13.6For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e.Received 21 March 2006Accepted 8 April 20063-Substituted phthalides,Part III. # 2006 International Union of CrystallographyAll rights reserved The title compound, C 15 H 13 NO 3 , contains an intramolecularN—H ÁÁÁ O hydrogen bond and the packing is stabilized byN—H ÁÁÁ O and C—H ÁÁÁ O intermolecular hydrogen bonds.The N—H ÁÁÁ O hydrogen bonds generate S (5)[ R 22 (12)] S (5)motifs and these motifs are bonded to each other by C—H ÁÁÁ O intermolecular hydrogen bonds. The phthalide group isplanar, showing a dihedral angle of 63.26 (8)  with thebenzene ring. Comment Phthalides are known to show diverse biological activities ashormones, pheromones and antibiotics. As part of our ongoingresearch on 3-substituted phthalides, the title compound, (I),has been synthesized and its crystal structure is reported here.The overall view and labeling of the molecule are displayedin Fig. 1. Selected bond lengths and angles are presented inTable 1, hydrogen bonding parameters are given in Table 2and the packing arrangement of the molecules within thecrystal structure is shown in Fig. 2. The phthalide part (C1through C8) of the molecule is essentially planar, the largestdeviation from the mean plane being 0.010 (2) A˚for atom C1.The dihedral angle between the five-membered ring and thefused six-membered ring is 1.29 (8)  , whereas the dihedralangle between the mean plane of the phthalide system andbenzene ring is 63.26 (8)  . The geometry of the molecule doesnot show any significant differences from the averagegeometry found for 3-(2-hydroxyanilino)isobenzofuran-1(3 H  )-one (Odabas¸og ˘lu & Bu ¨ yu ¨ kgu ¨ ngo ¨ r, 2006 a ).Two enantiomeric molecules of (I) are linked by N—H ÁÁÁ Ohydrogen bonds. These N—H ÁÁÁ O hydrogen bonds generate R 22 (12) rings (Etter, 1990), which also have two edge-fused S (5) rings, resulting in an S (5)[ R 22 (12)] S (5) motif (Fig. 2 andTable 2). Experimental The title compound was prepared as described by Odabas¸og ˘lu &Bu ¨ yu ¨ kgu ¨ ngo ¨ r (2006 b ), using phthalaldehydic acid and o -methoxy- electronic reprint  aniline as starting materials (yield 95%; m.p. 427–428 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol (95%) solution at room temperature. Crystal data C 15 H 13 NO 3 M  r  = 255.26Triclinic, P 1 a = 8.1259 (10) A˚ b = 8.2644 (11) A˚ c = 10.6641 (13) A˚  = 87.136 (11)   = 78.290 (10)    = 61.155 (9)  V  = 613.28 (15) A˚ 3 Z  = 2 D  x = 1.382 Mg m À 3 Mo K   radiation  = 0.10 mm À 1 T  = 296 (2) KPrism, brown0.50 Â 0.32 Â 0.21 mm Data collection Stoe IPDS-2 diffractometer ! scansAbsorption correction: integration(  X-RED32 ; Stoe & Cie, 2002) T  min = 0.970, T  max = 0.9868287 measured reflections2399 independent reflections1774 reflections with I  > 2   (  I  ) R int = 0.049   max = 26.0  Refinement  Refinement on F  2 R [ F  2 > 2   ( F  2 )] = 0.040 wR ( F  2 ) = 0.100 S = 1.032399 reflections176 parametersH atoms treated by a mixture of independent and constrainedrefinement w = 1/[   2 ( F  o2 ) + (0.0446 P ) 2 + 0.0674 P ]where P = ( F  o2 + 2 F  c2 )/3( Á /   ) max < 0.001 Á  max = 0.12 e A˚ À 3 Á  min = À 0.14 e A˚ À 3 Table 1 Selected geometric parameters (A˚,  ). C1—O1 1.2061 (19)C1—O2 1.3502 (19)C2—C7 1.376 (2)C7—C8 1.498 (2)C8—N1 1.3913 (19)C8—O2 1.4961 (18)C9—N1 1.3976 (19)O1—C1—O2 121.90 (15)O1—C1—C2 129.47 (15)N1—C8—O2 112.46 (12)N1—C8—C7 114.88 (13) 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 O3 0.86 (2) 2.286 (18) 2.6193 (18) 103.3 (16)N1—H1 ÁÁÁ O1 i 0.857 (18) 2.441 (18) 3.224 (2) 152.1 (15)C15—H15 B ÁÁÁ O1 ii 0.96 2.54 3.387 (2) 147 Symmetry codes: (i) À  x þ 1 ; À  y ; À z þ 1; (ii) x ;  y ; z þ 1. All C-bound H atoms were refined using the riding-modelapproximation, with C—H = 0.93 A˚for aromatic, 0.98 A˚for methineand 0.96 A˚for methyl H atoms [ U  iso (H) = 1.2 U  eq (parent atom)]. TheN-bound H atom was located in a Fourier difference map and refinedfreely.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, 1997); 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). 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 , o1879–o1881.Odabas¸og ˘lu, M. & Bu ¨ yu ¨ kgu ¨ ngo ¨ r, O. (2006 b ). Acta Cryst. E 62 , o1882–o1883.Sheldrick, G. M. (1997). SHELXS97  and 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 , o1884–o1885 Odabas¸og˘lu and Bu¨ yu¨ kgu¨ ngo¨ r  C 15 H 13 NO 3 o1885 Figure 1 A view of (I), with the atomic numbering scheme; the intramolecularhydrogen bond is shown as a dashed line. Displacement ellipsoids aredrawn at the 50% probability level. Figure 2 A view showing the formation of a dimer through N—H ÁÁÁ O hydrogenbonds (dashed lines). H atoms not involved in hydrogen bonding havebeen omitted for clarity. [Symmetry code: (i) 1 À x , À  y , 1 À z ] electronic reprint
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