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

Odabaşoğlu, M.; Büyükgüngör, O.

doi:10.1107/S1600536808008441

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o780

doi:10.1107/S1600536808008441

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3-(2-Hydroxy-5-methylanilino)isobenzofuran-1(3H)-one †

Mustafa Odabaşoğlu ^a and Orhan Büyükgüngör ^b ^*

^aDepartment of Chemistry, Faculty of Arts & Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, and ^bDepartment of Physics, Faculty of Arts & Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
^*Correspondence e-mail: muodabas@omu.edu.tr

(Received 28 March 2008; accepted 28 March 2008; online 2 April 2008)

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 ). For ring-motif details, see: Bernstein et al. (1995 ); Etter (1990 ).

Experimental

Crystal data

C₁₅H₁₃NO₃
M_r = 255.26
Orthorhombic, P n a 2₁
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 ) 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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.066
S = 0.99
1418 reflections
175 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.08 e Å⁻³
Δρ_min = −0.09 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.82	1.95	2.767 (2)	173
N1—H1⋯O2ⁱⁱ	0.86	2.78	3.5593 (19)	152
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

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, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	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.

3-(2-Hydroxy-5-methylanilino)isobenzofuran-1(3H)-one top

Crystal data top

C₁₅H₁₃NO₃	F(000) = 536
M_r = 255.26	D_x = 1.327 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4658 reflections
a = 8.7198 (5) Å	θ = 2.2–27.2°
b = 15.5950 (14) Å	µ = 0.09 mm⁻¹
c = 9.3992 (6) Å	T = 296 K
V = 1278.15 (16) Å³	Prism, colorless
Z = 4	0.64 × 0.42 × 0.28 mm

Data collection top

Stoe IPDSII diffractometer	1418 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1196 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.027
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.7°, θ_min = 2.5°
ω rotation method scans	h = −11→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→19
T_min = 0.957, T_max = 0.982	l = −10→11
4658 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0415P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
1418 reflections	Δρ_max = 0.08 e Å⁻³
175 parameters	Δρ_min = −0.09 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

Crystal data top

C₁₅H₁₃NO₃	V = 1278.15 (16) Å³
M_r = 255.26	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.7198 (5) Å	µ = 0.09 mm⁻¹
b = 15.5950 (14) Å	T = 296 K
c = 9.3992 (6) Å	0.64 × 0.42 × 0.28 mm

Data collection top

Stoe IPDSII diffractometer	1418 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1196 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.982	R_int = 0.027
4658 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.066	H-atom parameters constrained
S = 0.99	Δρ_max = 0.08 e Å⁻³
1418 reflections	Δρ_min = −0.09 e Å⁻³
175 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O1	0.40903 (18)	0.07832 (10)	0.36000 (19)	0.0720 (4)
O2	0.45824 (13)	0.20974 (10)	0.43987 (15)	0.0570 (4)
O3	0.20122 (14)	0.44221 (12)	0.70125 (18)	0.0703 (5)
H3A	0.1679	0.4796	0.7542	0.105*
N1	0.34673 (16)	0.34164 (11)	0.51886 (18)	0.0520 (4)
H1	0.2484	0.3454	0.5210	0.062*
C1	0.3901 (2)	0.15492 (14)	0.3495 (2)	0.0545 (5)
C2	0.3001 (2)	0.20426 (14)	0.2462 (2)	0.0525 (5)
C3	0.2126 (2)	0.17580 (17)	0.1316 (3)	0.0669 (6)
H3	0.2014	0.1177	0.1121	0.080*
C4	0.1436 (3)	0.23701 (19)	0.0486 (3)	0.0749 (7)
H4	0.0837	0.2199	−0.0283	0.090*
C5	0.1609 (3)	0.32357 (18)	0.0765 (3)	0.0726 (6)
H5	0.1146	0.3636	0.0169	0.087*
C6	0.2468 (2)	0.35171 (17)	0.1926 (2)	0.0631 (6)
H6	0.2576	0.4098	0.2129	0.076*
C7	0.31506 (19)	0.28990 (15)	0.2760 (2)	0.0517 (5)
C8	0.41502 (19)	0.30062 (13)	0.4044 (2)	0.0495 (4)
H8	0.5076	0.3322	0.3771	0.059*
C9	0.43056 (19)	0.37720 (11)	0.6310 (2)	0.0433 (4)
C10	0.35434 (19)	0.43126 (13)	0.7257 (2)	0.0491 (4)
C11	0.4335 (2)	0.46949 (13)	0.8349 (2)	0.0533 (5)
H11	0.3819	0.5041	0.8997	0.064*
C12	0.5902 (2)	0.45668 (13)	0.8491 (2)	0.0548 (5)
H12	0.6432	0.4842	0.9217	0.066*
C13	0.6683 (2)	0.40359 (14)	0.7568 (2)	0.0511 (4)
C14	0.5859 (2)	0.36305 (13)	0.6500 (2)	0.0493 (4)
H14	0.6364	0.3253	0.5895	0.059*
C15	0.8385 (2)	0.3893 (2)	0.7713 (3)	0.0793 (7)
H15A	0.8895	0.4095	0.6872	0.119*
H15B	0.8584	0.3292	0.7833	0.119*
H15C	0.8760	0.4201	0.8526	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0755 (9)	0.0573 (10)	0.0832 (11)	−0.0036 (7)	−0.0069 (9)	−0.0174 (9)
O2	0.0564 (6)	0.0588 (9)	0.0558 (7)	−0.0021 (6)	−0.0041 (7)	−0.0153 (7)
O3	0.0509 (7)	0.0807 (12)	0.0793 (10)	0.0085 (7)	−0.0030 (8)	−0.0320 (8)
N1	0.0421 (7)	0.0615 (10)	0.0523 (9)	−0.0042 (7)	0.0017 (7)	−0.0164 (8)
C1	0.0486 (9)	0.0570 (12)	0.0580 (11)	−0.0076 (9)	0.0066 (9)	−0.0176 (11)
C2	0.0469 (9)	0.0619 (13)	0.0488 (10)	−0.0091 (8)	0.0069 (8)	−0.0155 (10)
C3	0.0619 (11)	0.0785 (17)	0.0603 (12)	−0.0107 (11)	−0.0022 (10)	−0.0241 (13)
C4	0.0698 (13)	0.095 (2)	0.0599 (13)	−0.0043 (12)	−0.0101 (11)	−0.0271 (14)
C5	0.0718 (13)	0.0891 (19)	0.0571 (12)	0.0046 (12)	−0.0071 (10)	−0.0059 (12)
C6	0.0643 (12)	0.0654 (15)	0.0597 (12)	−0.0035 (10)	−0.0028 (10)	−0.0063 (11)
C7	0.0454 (9)	0.0633 (13)	0.0465 (10)	−0.0068 (8)	0.0053 (8)	−0.0110 (10)
C8	0.0457 (8)	0.0528 (11)	0.0501 (11)	−0.0061 (8)	0.0012 (8)	−0.0103 (9)
C9	0.0503 (9)	0.0392 (10)	0.0405 (8)	−0.0068 (7)	0.0015 (8)	−0.0007 (8)
C10	0.0501 (9)	0.0467 (11)	0.0506 (10)	−0.0026 (7)	0.0022 (8)	−0.0032 (9)
C11	0.0655 (11)	0.0466 (11)	0.0480 (10)	0.0007 (8)	−0.0011 (9)	−0.0087 (9)
C12	0.0683 (11)	0.0502 (11)	0.0460 (10)	−0.0103 (9)	−0.0089 (9)	−0.0013 (10)
C13	0.0526 (9)	0.0551 (12)	0.0456 (10)	−0.0060 (9)	−0.0040 (9)	0.0050 (9)
C14	0.0502 (9)	0.0523 (12)	0.0453 (10)	−0.0004 (8)	0.0044 (8)	−0.0021 (9)
C15	0.0531 (11)	0.115 (2)	0.0695 (14)	−0.0051 (12)	−0.0079 (11)	−0.0088 (15)

Geometric parameters (Å, º) top

O3—H3A	0.8200	C8—O2	1.504 (3)
N1—H1	0.8600	C8—H8	0.9800
C1—O1	1.210 (3)	C9—C14	1.384 (2)
C1—O2	1.344 (2)	C9—C10	1.394 (3)
C1—C2	1.466 (3)	C9—N1	1.397 (2)
C2—C7	1.371 (3)	C10—O3	1.366 (2)
C2—C3	1.393 (3)	C10—C11	1.373 (3)
C3—C4	1.372 (4)	C11—C12	1.387 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.383 (4)	C12—C13	1.379 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.395 (3)	C13—C14	1.387 (3)
C5—H5	0.9300	C13—C15	1.506 (3)
C6—C7	1.378 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—H15A	0.9600
C7—C8	1.498 (3)	C15—H15B	0.9600
C8—N1	1.386 (2)	C15—H15C	0.9600

O1—C1—O2	121.1 (2)	C14—C9—N1	123.10 (16)
O1—C1—C2	130.19 (19)	C10—C9—N1	118.16 (15)
O2—C1—C2	108.75 (18)	O3—C10—C11	124.26 (17)
C7—C2—C3	121.4 (2)	O3—C10—C9	115.74 (16)
C7—C2—C1	108.97 (16)	C11—C10—C9	120.00 (16)
C3—C2—C1	129.7 (2)	C10—C11—C12	120.27 (18)
C4—C3—C2	117.3 (2)	C10—C11—H11	119.9
C4—C3—H3	121.4	C12—C11—H11	119.9
C2—C3—H3	121.4	C13—C12—C11	120.84 (17)
C3—C4—C5	121.5 (2)	C13—C12—H12	119.6
C3—C4—H4	119.2	C11—C12—H12	119.6
C5—C4—H4	119.2	C12—C13—C14	118.20 (16)
C4—C5—C6	120.9 (2)	C12—C13—C15	121.22 (18)
C4—C5—H5	119.5	C14—C13—C15	120.58 (19)
C6—C5—H5	119.5	C9—C14—C13	121.89 (17)
C7—C6—C5	117.2 (2)	C9—C14—H14	119.1
C7—C6—H6	121.4	C13—C14—H14	119.1
C5—C6—H6	121.4	C13—C15—H15A	109.5
C2—C7—C6	121.62 (19)	C13—C15—H15B	109.5
C2—C7—C8	109.19 (19)	H15A—C15—H15B	109.5
C6—C7—C8	129.2 (2)	C13—C15—H15C	109.5
N1—C8—C7	115.26 (14)	H15A—C15—H15C	109.5
N1—C8—O2	111.73 (16)	H15B—C15—H15C	109.5
C7—C8—O2	102.67 (15)	C8—N1—C9	122.95 (13)
N1—C8—H8	109.0	C8—N1—H1	118.5
C7—C8—H8	109.0	C9—N1—H1	118.5
O2—C8—H8	109.0	C1—O2—C8	110.39 (16)
C14—C9—C10	118.71 (16)	C10—O3—H3A	109.5

O1—C1—C2—C7	−179.2 (2)	N1—C9—C10—O3	1.9 (3)
O2—C1—C2—C7	−0.1 (2)	C14—C9—C10—C11	0.2 (3)
O1—C1—C2—C3	−0.4 (4)	N1—C9—C10—C11	−178.11 (17)
O2—C1—C2—C3	178.76 (19)	O3—C10—C11—C12	−178.1 (2)
C7—C2—C3—C4	0.8 (3)	C9—C10—C11—C12	2.0 (3)
C1—C2—C3—C4	−177.9 (2)	C10—C11—C12—C13	−1.9 (3)
C2—C3—C4—C5	0.5 (3)	C11—C12—C13—C14	−0.3 (3)
C3—C4—C5—C6	−1.5 (4)	C11—C12—C13—C15	180.0 (2)
C4—C5—C6—C7	1.0 (3)	C10—C9—C14—C13	−2.5 (3)
C3—C2—C7—C6	−1.3 (3)	N1—C9—C14—C13	175.70 (19)
C1—C2—C7—C6	177.66 (17)	C12—C13—C14—C9	2.6 (3)
C3—C2—C7—C8	179.96 (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—C2	0.3 (3)	O2—C8—N1—C9	80.7 (2)
C5—C6—C7—C8	178.81 (19)	C14—C9—N1—C8	−10.7 (3)
C2—C7—C8—N1	−120.00 (19)	C10—C9—N1—C8	167.55 (18)
C6—C7—C8—N1	61.4 (3)	O1—C1—O2—C8	−179.57 (18)
C2—C7—C8—O2	1.72 (17)	C2—C1—O2—C8	1.21 (19)
C6—C7—C8—O2	−176.92 (18)	N1—C8—O2—C1	122.30 (16)
C14—C9—C10—O3	−179.76 (17)	C7—C8—O2—C1	−1.79 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.82	1.95	2.767 (2)	173
N1—H1···O2ⁱⁱ	0.86	2.78	3.5593 (19)	152

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₃
M_r	255.26
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	8.7198 (5), 15.5950 (14), 9.3992 (6)
V (Å³)	1278.15 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.64 × 0.42 × 0.28

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.957, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	4658, 1418, 1196
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.066, 0.99
No. of reflections	1418
No. of parameters	175
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.08, −0.09

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.82	1.95	2.767 (2)	172.8
N1—H1···O2ⁱⁱ	0.86	2.78	3.5593 (19)	151.8

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

Footnotes

†3-Substituted phthalides. Part XXXVII.

Acknowledgements

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).

References

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