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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o780.
Published online 2008 April 2. doi:  10.1107/S1600536808008441
PMCID: PMC2961204

3-(2-Hydr­oxy-5-methyl­anilino)isobenzo­furan-1(3H)-one1

Abstract

In the mol­ecule of the title compound, C15H13NO3, the phthalide ring system is virtually planar, with a dihedral angle of 1.98 (3)° between the fused five- and six-membered rings. The substituted aromatic ring is oriented at a dihedral angle of 57.50 (3)° with respect to the phthalide ring system. In the crystal structure, inter­molecular O—H(...)O and N—H(...)O hydrogen bonds link the mol­ecules, forming a three-dimensional network.

Related literature

For a related structure, see: Odabaşoğlu & Büyükgüngör (2006 [triangle]). For ring-motif details, see: Bernstein et al. (1995 [triangle]); Etter (1990 [triangle]).

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Object name is e-64-0o780-scheme1.jpg

Experimental

Crystal data

  • C15H13NO3
  • M r = 255.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o780-efi3.jpg
  • a = 8.7198 (5) Å
  • b = 15.5950 (14) Å
  • c = 9.3992 (6) Å
  • V = 1278.15 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.64 × 0.42 × 0.28 mm

Data collection

  • Stoe IPDSII diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.957, T max = 0.982
  • 4658 measured reflections
  • 1418 independent reflections
  • 1196 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.066
  • S = 0.99
  • 1418 reflections
  • 175 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.08 e Å−3
  • Δρmin = −0.09 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008441/hk2444sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008441/hk2444Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

The present work is part of a structural study of compounds of 3-substituted phthalides, and we report here the crystal structure of the title compound, (I).

The molecule of (I), (Fig. 1), is built up from a phthalimide unit connected to 2-hydroxy-5-methylphnyl group through an amino group. Rings A (C2-C7), B (C1/C2/C7/C8/O2) and C (C9-C14) are, of course, planar. The dihedral angles between them are A/B = 1.98 (3)°, A/C = 58.27 (3)° and B/C = 56.39 (3)°. So, rings A and B are also nearly coplanar. Ring C is oriented with respect to the coplanar ring system at a dihedral angle of 57.50 (3)°.

In the crystal structure, intermolecular O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules by C(4) chains (Fig. 2) (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network (Fig. 3), in which they may be effective in the stabilization of the structure.

Experimental

The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006), using phthalaldehydic acid and 2-aminophenol as starting materials (yield; 80%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol-DMF (1:1) solution at room temperature.

Refinement

H atoms were positioned geometrically, with O-H = 0.82 Å (for OH), N-H = 0.86 Å (for NH) and C-H = 0.93 and 0.98 Å for aromatic and methine H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,O,N), where x = 1.5 for OH and NH H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A partial packing diagram of (I), showing the formation of C(4) chain along the [100] direction. Hydrogen bonds are shown as dashed lines [symmetry code: (i) 1 - x, -y, z + 1/2]. H atoms not involved in hydrogen bondings have been omitted for clarity. ...
Fig. 3.
A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines [symmetry code: (i) 1 - x, -y, z + 1/2]. H atoms not involved in hydrogen bondings have been omitted for clarity.

Crystal data

C15H13NO3F000 = 536
Mr = 255.26Dx = 1.327 Mg m3
Orthorhombic, Pna21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4658 reflections
a = 8.7198 (5) Åθ = 2.2–27.2º
b = 15.5950 (14) ŵ = 0.09 mm1
c = 9.3992 (6) ÅT = 296 K
V = 1278.15 (16) Å3Prism, colorless
Z = 40.64 × 0.42 × 0.28 mm

Data collection

Stoe IPDSII diffractometer1418 independent reflections
Monochromator: plane graphite1196 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.027
T = 296 Kθmax = 26.7º
ω rotation method scansθmin = 2.5º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)h = −11→10
Tmin = 0.957, Tmax = 0.982k = −12→19
4658 measured reflectionsl = −10→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.066  w = 1/[σ2(Fo2) + (0.0415P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
1418 reflectionsΔρmax = 0.08 e Å3
175 parametersΔρmin = −0.08 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (2)

Special 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 taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used 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 > 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)

xyzUiso*/Ueq
O10.40903 (18)0.07832 (10)0.36000 (19)0.0720 (4)
O20.45824 (13)0.20974 (10)0.43987 (15)0.0570 (4)
O30.20122 (14)0.44221 (12)0.70125 (18)0.0703 (5)
H3A0.16790.47960.75420.105*
N10.34673 (16)0.34164 (11)0.51886 (18)0.0520 (4)
H10.24840.34540.52100.062*
C10.3901 (2)0.15492 (14)0.3495 (2)0.0545 (5)
C20.3001 (2)0.20426 (14)0.2462 (2)0.0525 (5)
C30.2126 (2)0.17580 (17)0.1316 (3)0.0669 (6)
H30.20140.11770.11210.080*
C40.1436 (3)0.23701 (19)0.0486 (3)0.0749 (7)
H40.08370.2199−0.02830.090*
C50.1609 (3)0.32357 (18)0.0765 (3)0.0726 (6)
H50.11460.36360.01690.087*
C60.2468 (2)0.35171 (17)0.1926 (2)0.0631 (6)
H60.25760.40980.21290.076*
C70.31506 (19)0.28990 (15)0.2760 (2)0.0517 (5)
C80.41502 (19)0.30062 (13)0.4044 (2)0.0495 (4)
H80.50760.33220.37710.059*
C90.43056 (19)0.37720 (11)0.6310 (2)0.0433 (4)
C100.35434 (19)0.43126 (13)0.7257 (2)0.0491 (4)
C110.4335 (2)0.46949 (13)0.8349 (2)0.0533 (5)
H110.38190.50410.89970.064*
C120.5902 (2)0.45668 (13)0.8491 (2)0.0548 (5)
H120.64320.48420.92170.066*
C130.6683 (2)0.40359 (14)0.7568 (2)0.0511 (4)
C140.5859 (2)0.36305 (13)0.6500 (2)0.0493 (4)
H140.63640.32530.58950.059*
C150.8385 (2)0.3893 (2)0.7713 (3)0.0793 (7)
H15A0.88950.40950.68720.119*
H15B0.85840.32920.78330.119*
H15C0.87600.42010.85260.119*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0755 (9)0.0573 (10)0.0832 (11)−0.0036 (7)−0.0069 (9)−0.0174 (9)
O20.0564 (6)0.0588 (9)0.0558 (7)−0.0021 (6)−0.0041 (7)−0.0153 (7)
O30.0509 (7)0.0807 (12)0.0793 (10)0.0085 (7)−0.0030 (8)−0.0320 (8)
N10.0421 (7)0.0615 (10)0.0523 (9)−0.0042 (7)0.0017 (7)−0.0164 (8)
C10.0486 (9)0.0570 (12)0.0580 (11)−0.0076 (9)0.0066 (9)−0.0176 (11)
C20.0469 (9)0.0619 (13)0.0488 (10)−0.0091 (8)0.0069 (8)−0.0155 (10)
C30.0619 (11)0.0785 (17)0.0603 (12)−0.0107 (11)−0.0022 (10)−0.0241 (13)
C40.0698 (13)0.095 (2)0.0599 (13)−0.0043 (12)−0.0101 (11)−0.0271 (14)
C50.0718 (13)0.0891 (19)0.0571 (12)0.0046 (12)−0.0071 (10)−0.0059 (12)
C60.0643 (12)0.0654 (15)0.0597 (12)−0.0035 (10)−0.0028 (10)−0.0063 (11)
C70.0454 (9)0.0633 (13)0.0465 (10)−0.0068 (8)0.0053 (8)−0.0110 (10)
C80.0457 (8)0.0528 (11)0.0501 (11)−0.0061 (8)0.0012 (8)−0.0103 (9)
C90.0503 (9)0.0392 (10)0.0405 (8)−0.0068 (7)0.0015 (8)−0.0007 (8)
C100.0501 (9)0.0467 (11)0.0506 (10)−0.0026 (7)0.0022 (8)−0.0032 (9)
C110.0655 (11)0.0466 (11)0.0480 (10)0.0007 (8)−0.0011 (9)−0.0087 (9)
C120.0683 (11)0.0502 (11)0.0460 (10)−0.0103 (9)−0.0089 (9)−0.0013 (10)
C130.0526 (9)0.0551 (12)0.0456 (10)−0.0060 (9)−0.0040 (9)0.0050 (9)
C140.0502 (9)0.0523 (12)0.0453 (10)−0.0004 (8)0.0044 (8)−0.0021 (9)
C150.0531 (11)0.115 (2)0.0695 (14)−0.0051 (12)−0.0079 (11)−0.0088 (15)

Geometric parameters (Å, °)

O3—H3A0.8200C8—O21.504 (3)
N1—H10.8600C8—H80.9800
C1—O11.210 (3)C9—C141.384 (2)
C1—O21.344 (2)C9—C101.394 (3)
C1—C21.466 (3)C9—N11.397 (2)
C2—C71.371 (3)C10—O31.366 (2)
C2—C31.393 (3)C10—C111.373 (3)
C3—C41.372 (4)C11—C121.387 (3)
C3—H30.9300C11—H110.9300
C4—C51.383 (4)C12—C131.379 (3)
C4—H40.9300C12—H120.9300
C5—C61.395 (3)C13—C141.387 (3)
C5—H50.9300C13—C151.506 (3)
C6—C71.378 (3)C14—H140.9300
C6—H60.9300C15—H15A0.9600
C7—C81.498 (3)C15—H15B0.9600
C8—N11.386 (2)C15—H15C0.9600
O1—C1—O2121.1 (2)C14—C9—N1123.10 (16)
O1—C1—C2130.19 (19)C10—C9—N1118.16 (15)
O2—C1—C2108.75 (18)O3—C10—C11124.26 (17)
C7—C2—C3121.4 (2)O3—C10—C9115.74 (16)
C7—C2—C1108.97 (16)C11—C10—C9120.00 (16)
C3—C2—C1129.7 (2)C10—C11—C12120.27 (18)
C4—C3—C2117.3 (2)C10—C11—H11119.9
C4—C3—H3121.4C12—C11—H11119.9
C2—C3—H3121.4C13—C12—C11120.84 (17)
C3—C4—C5121.5 (2)C13—C12—H12119.6
C3—C4—H4119.2C11—C12—H12119.6
C5—C4—H4119.2C12—C13—C14118.20 (16)
C4—C5—C6120.9 (2)C12—C13—C15121.22 (18)
C4—C5—H5119.5C14—C13—C15120.58 (19)
C6—C5—H5119.5C9—C14—C13121.89 (17)
C7—C6—C5117.2 (2)C9—C14—H14119.1
C7—C6—H6121.4C13—C14—H14119.1
C5—C6—H6121.4C13—C15—H15A109.5
C2—C7—C6121.62 (19)C13—C15—H15B109.5
C2—C7—C8109.19 (19)H15A—C15—H15B109.5
C6—C7—C8129.2 (2)C13—C15—H15C109.5
N1—C8—C7115.26 (14)H15A—C15—H15C109.5
N1—C8—O2111.73 (16)H15B—C15—H15C109.5
C7—C8—O2102.67 (15)C8—N1—C9122.95 (13)
N1—C8—H8109.0C8—N1—H1118.5
C7—C8—H8109.0C9—N1—H1118.5
O2—C8—H8109.0C1—O2—C8110.39 (16)
C14—C9—C10118.71 (16)C10—O3—H3A109.5
O1—C1—C2—C7−179.2 (2)N1—C9—C10—O31.9 (3)
O2—C1—C2—C7−0.1 (2)C14—C9—C10—C110.2 (3)
O1—C1—C2—C3−0.4 (4)N1—C9—C10—C11−178.11 (17)
O2—C1—C2—C3178.76 (19)O3—C10—C11—C12−178.1 (2)
C7—C2—C3—C40.8 (3)C9—C10—C11—C122.0 (3)
C1—C2—C3—C4−177.9 (2)C10—C11—C12—C13−1.9 (3)
C2—C3—C4—C50.5 (3)C11—C12—C13—C14−0.3 (3)
C3—C4—C5—C6−1.5 (4)C11—C12—C13—C15180.0 (2)
C4—C5—C6—C71.0 (3)C10—C9—C14—C13−2.5 (3)
C3—C2—C7—C6−1.3 (3)N1—C9—C14—C13175.70 (19)
C1—C2—C7—C6177.66 (17)C12—C13—C14—C92.6 (3)
C3—C2—C7—C8179.96 (17)C15—C13—C14—C9−177.7 (2)
C1—C2—C7—C8−1.11 (19)C7—C8—N1—C9−162.60 (18)
C5—C6—C7—C20.3 (3)O2—C8—N1—C980.7 (2)
C5—C6—C7—C8178.81 (19)C14—C9—N1—C8−10.7 (3)
C2—C7—C8—N1−120.00 (19)C10—C9—N1—C8167.55 (18)
C6—C7—C8—N161.4 (3)O1—C1—O2—C8−179.57 (18)
C2—C7—C8—O21.72 (17)C2—C1—O2—C81.21 (19)
C6—C7—C8—O2−176.92 (18)N1—C8—O2—C1122.30 (16)
C14—C9—C10—O3−179.76 (17)C7—C8—O2—C1−1.79 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3A···O1i0.821.952.767 (2)173
N1—H1···O2ii0.862.783.5593 (19)152

Symmetry codes: (i) −x+1/2, y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z.

Footnotes

13-Substituted phthalides. Part XXXVII.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2444).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • 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.
  • Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1879–o1881.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (2002). X-AREA and X-RED32 Stoe & Cie, Darmstadt, Germany.

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