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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o752–o753.
Published online 2008 March 29. doi:  10.1107/S160053680800754X
PMCID: PMC2960995

2-(3-Oxo-1,3-dihydro­isobenzofuran-1-ylamino)benzoic acid1

Abstract

In the mol­ecule of the title compound, C15H11NO4, the essentially planar phthalide group is oriented at a dihedral angle of 56.78 (5)° with respect to the substituted aromatic ring. An intra­molecular N—H(...)O hydrogen bond results in the formation of a non-planar six-membered ring, which adopts a nearly flattened-boat conformation. In the crystal structure, inter­molecular C—H(...)O, O—H(...)O and N—H(...)O hydrogen bonds link the mol­ecules, generating centrosymmetric R 2 2(8) and R 2 2(11) ring motifs and forming a three-dimensional network.

Related literature

For general background, see: Aoki et al. (1973 [triangle], 1974 [triangle]); Lacova (1973 [triangle], 1974 [triangle]); Elderfield (1951 [triangle]); Bellasio (1974 [triangle], 1975 [triangle]); Roy & Sarkar (2005 [triangle]); Kubota & Tatsuno (1971 [triangle]); Tsi & Tan (1997 [triangle]). For related structures, see: Büyükgüngör & Odabaşoğlu (2006 [triangle]); Odabaşoğlu & Büyükgüngör (2006 [triangle]; 2007 [triangle]). For ring puckering parameters, see: Cremer & Pople (1975 [triangle]). For ring motif details, see: Bernstein et al. (1995 [triangle]); Etter (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o752-scheme1.jpg

Experimental

Crystal data

  • C15H11NO4
  • M r = 269.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o752-efi3.jpg
  • a = 7.8135 (6) Å
  • b = 22.6205 (10) Å
  • c = 7.0902 (5) Å
  • β = 101.061 (5)°
  • V = 1229.88 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 296 K
  • 0.55 × 0.36 × 0.18 mm

Data collection

  • Stoe IPDS II diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.958, T max = 0.982
  • 12715 measured reflections
  • 2536 independent reflections
  • 1958 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.093
  • S = 1.07
  • 2536 reflections
  • 225 parameters
  • All H-atom parameters refined
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.17 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/S160053680800754X/hk2434sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800754X/hk2434Isup2.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 IPDS II diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

Phthalides are known to show diverse biological activities as hormones, pheromones and antibiotics (Aoki et al., 1973, 1974; Lacova, 1973, 1974; Elderfield, 1951; Bellasio, 1974, 1975; Roy & Sarkar, 2005; Kubota & Tatsuno, 1971; Tsi & Tan, 1997). As part of our ongoing research on 3-substituted phthalides (Büyükgüngör & Odabaşoğlu, 2006; Odabaşoğlu & Büyükgüngör, 2006; 2007), the title compound, (I), has been synthesized and its crystal structure is reported here.

In the molecule of (I), (Fig. 1), 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 = 3.08 (3)°, A/C = 57.11 (4)° and B/C = 56.56 (5)°. 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 56.78 (5)°. The intramolecular N-H···O hydrogen bond (Table 1) results in the formation of a non-planar six-membered ring D (N1/H1/O3/C9/C10/C15), having total puckering amplitude, QT, of 1.408 (3) Å, in which it adopts a nearly flattened-boat [[var phi] = -42.43 (2)° and θ = 97.94 (3)°] conformation (Cremer & Pople, 1975).

In the crystal structure, intermolecular C-H···O, O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules, generating centrosymmetric R22(8) and R22(11) (Fig. 2) ring motifs (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network, 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 antranilic acid as starting materials (yield; 70%). 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 located in difference synthesis and refined freely [C-H = 0.93 (2)-0.983 (18) Å and Uiso(H) = 0.036 (4)-0.060 (6) Å2; N-H = 0.86 (2) Å and Uiso(H) = 0.046 (5) Å2; O-H = 0.97 (3) Å and Uiso(H) = 0.094 (9) Å2].

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dashed line.
Fig. 2.
A partial packing diagram of (I), showing the formation of R22(8) and R22(11) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x, 1/2 - y, z - 1/2; (ii) 1 - x, -y, 2 - z]. H atoms not involved in hydrogen bondings have been omitted ...

Crystal data

C15H11NO4F000 = 560
Mr = 269.25Dx = 1.454 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12715 reflections
a = 7.8135 (6) Åθ = 1.8–27.3º
b = 22.6205 (10) ŵ = 0.11 mm1
c = 7.0902 (5) ÅT = 296 K
β = 101.061 (5)ºPrism, colorless
V = 1229.88 (14) Å30.55 × 0.36 × 0.18 mm
Z = 4

Data collection

Stoe IPDSII diffractometer2536 independent reflections
Monochromator: plane graphite1958 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.034
T = 296 Kθmax = 26.5º
ω scan rotation methodθmin = 1.8º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)h = −9→9
Tmin = 0.958, Tmax = 0.982k = −28→28
12715 measured reflectionsl = −8→8

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043All H-atom parameters refined
wR(F2) = 0.093  w = 1/[σ2(Fo2) + (0.0403P)2 + 0.2251P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2536 reflectionsΔρmax = 0.16 e Å3
225 parametersΔρmin = −0.17 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
C10.6576 (2)0.26649 (7)0.4899 (2)0.0402 (4)
C20.8303 (2)0.24430 (7)0.5812 (2)0.0367 (4)
C30.9781 (3)0.27532 (8)0.6650 (3)0.0457 (4)
C41.1272 (3)0.24364 (9)0.7337 (3)0.0518 (5)
C51.1279 (3)0.18248 (9)0.7191 (3)0.0511 (5)
C60.9805 (2)0.15141 (8)0.6356 (3)0.0460 (4)
C70.8308 (2)0.18333 (7)0.5662 (2)0.0354 (4)
C80.6571 (2)0.16362 (7)0.4548 (3)0.0364 (4)
C90.4218 (2)0.09230 (6)0.4534 (2)0.0332 (4)
C100.3436 (2)0.04653 (6)0.5436 (2)0.0321 (3)
C110.1982 (2)0.01723 (7)0.4399 (3)0.0396 (4)
C120.1264 (2)0.03208 (8)0.2541 (3)0.0458 (4)
C130.2021 (2)0.07689 (8)0.1666 (3)0.0435 (4)
C140.3465 (2)0.10673 (7)0.2628 (2)0.0389 (4)
C150.4117 (2)0.02788 (6)0.7427 (2)0.0334 (3)
N10.56924 (19)0.12145 (6)0.5475 (2)0.0387 (3)
O10.60404 (19)0.31643 (5)0.4713 (2)0.0563 (4)
O20.55684 (15)0.21973 (5)0.41990 (18)0.0437 (3)
O30.53512 (17)0.05196 (5)0.84778 (17)0.0457 (3)
O40.32808 (17)−0.01696 (5)0.80153 (19)0.0481 (3)
H10.596 (2)0.1184 (8)0.670 (3)0.046 (5)*
H30.975 (3)0.3188 (9)0.671 (3)0.058 (6)*
H41.229 (3)0.2630 (9)0.792 (3)0.060 (6)*
H4A0.383 (3)−0.0277 (11)0.931 (4)0.094 (9)*
H51.233 (3)0.1623 (8)0.764 (3)0.055 (6)*
H60.980 (3)0.1090 (9)0.626 (3)0.053 (5)*
H80.665 (2)0.1498 (7)0.325 (3)0.036 (4)*
H110.149 (2)−0.0136 (8)0.506 (3)0.045 (5)*
H120.030 (3)0.0113 (9)0.191 (3)0.055 (6)*
H130.154 (2)0.0893 (8)0.035 (3)0.049 (5)*
H140.394 (2)0.1377 (8)0.199 (3)0.047 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0518 (10)0.0365 (8)0.0337 (9)−0.0007 (7)0.0115 (8)0.0015 (6)
C20.0436 (9)0.0365 (8)0.0316 (8)−0.0055 (7)0.0113 (7)−0.0002 (6)
C30.0524 (11)0.0441 (10)0.0421 (10)−0.0141 (8)0.0130 (8)−0.0057 (8)
C40.0421 (11)0.0669 (12)0.0456 (11)−0.0212 (10)0.0068 (9)−0.0065 (9)
C50.0371 (10)0.0647 (12)0.0497 (11)0.0009 (9)0.0041 (9)0.0057 (9)
C60.0433 (10)0.0409 (9)0.0520 (11)0.0000 (8)0.0040 (8)0.0030 (8)
C70.0375 (9)0.0359 (8)0.0333 (9)−0.0051 (7)0.0080 (7)0.0024 (6)
C80.0389 (9)0.0318 (8)0.0373 (9)−0.0013 (7)0.0040 (7)0.0031 (6)
C90.0321 (8)0.0308 (7)0.0361 (9)0.0020 (6)0.0044 (7)−0.0020 (6)
C100.0298 (8)0.0316 (7)0.0351 (9)0.0028 (6)0.0066 (7)0.0001 (6)
C110.0329 (9)0.0422 (9)0.0429 (10)−0.0047 (7)0.0054 (7)−0.0011 (7)
C120.0366 (10)0.0522 (10)0.0448 (11)−0.0082 (8)−0.0017 (8)−0.0046 (8)
C130.0426 (10)0.0487 (10)0.0351 (10)0.0033 (8)−0.0025 (8)0.0010 (7)
C140.0400 (10)0.0378 (8)0.0375 (9)−0.0014 (7)0.0041 (7)0.0041 (7)
C150.0316 (8)0.0309 (7)0.0385 (9)−0.0003 (6)0.0089 (7)−0.0008 (6)
N10.0415 (8)0.0396 (7)0.0325 (8)−0.0098 (6)0.0010 (6)0.0048 (6)
O10.0735 (10)0.0368 (6)0.0577 (9)0.0114 (6)0.0107 (7)0.0040 (6)
O20.0425 (7)0.0373 (6)0.0479 (7)0.0009 (5)−0.0001 (6)0.0049 (5)
O30.0525 (8)0.0435 (6)0.0369 (7)−0.0141 (6)−0.0020 (6)0.0051 (5)
O40.0461 (7)0.0540 (7)0.0419 (7)−0.0159 (6)0.0028 (6)0.0113 (6)

Geometric parameters (Å, °)

O4—H4A0.97 (3)C8—O21.4872 (18)
N1—H10.86 (2)C8—H80.983 (18)
C1—O11.203 (2)C9—N11.383 (2)
C1—O21.355 (2)C9—C141.405 (2)
C1—C21.469 (2)C9—C101.415 (2)
C2—C71.383 (2)C10—C111.397 (2)
C2—C31.384 (2)C10—C151.472 (2)
C3—C41.375 (3)C11—C121.371 (3)
C3—H30.98 (2)C11—H110.96 (2)
C4—C51.387 (3)C12—C131.380 (3)
C4—H40.93 (2)C12—H120.93 (2)
C5—C61.382 (3)C13—C141.378 (2)
C5—H50.94 (2)C13—H130.98 (2)
C6—C71.382 (2)C14—H140.948 (19)
C6—H60.963 (19)C15—O31.2271 (19)
C7—C81.501 (2)C15—O41.3168 (19)
C8—N11.409 (2)
C1—O2—C8110.76 (12)N1—C8—C7115.34 (14)
C15—O4—H4A109.6 (15)O2—C8—C7103.22 (12)
C9—N1—C8122.22 (14)N1—C8—H8110.1 (10)
C9—N1—H1118.1 (13)O2—C8—H8104.0 (10)
C8—N1—H1118.7 (13)C7—C8—H8111.9 (10)
O1—C1—O2121.82 (16)N1—C9—C14120.64 (15)
O1—C1—C2129.81 (16)N1—C9—C10121.49 (14)
O2—C1—C2108.36 (13)C14—C9—C10117.86 (14)
C7—C2—C3121.61 (16)C11—C10—C9119.13 (15)
C7—C2—C1108.84 (14)C11—C10—C15118.49 (14)
C3—C2—C1129.51 (15)C9—C10—C15122.37 (14)
C4—C3—C2117.92 (17)C12—C11—C10122.10 (16)
C4—C3—H3122.0 (12)C12—C11—H11121.2 (11)
C2—C3—H3120.0 (12)C10—C11—H11116.7 (11)
C3—C4—C5120.56 (18)C11—C12—C13118.70 (16)
C3—C4—H4120.3 (13)C11—C12—H12119.0 (12)
C5—C4—H4119.1 (13)C13—C12—H12122.3 (13)
C6—C5—C4121.62 (19)C14—C13—C12121.22 (17)
C6—C5—H5120.1 (12)C14—C13—H13117.3 (11)
C4—C5—H5118.3 (12)C12—C13—H13121.5 (11)
C5—C6—C7117.75 (17)C13—C14—C9120.98 (16)
C5—C6—H6122.0 (12)C13—C14—H14118.8 (11)
C7—C6—H6120.3 (12)C9—C14—H14120.2 (11)
C6—C7—C2120.54 (16)O3—C15—O4121.99 (15)
C6—C7—C8130.55 (15)O3—C15—C10123.52 (14)
C2—C7—C8108.71 (14)O4—C15—C10114.49 (13)
N1—C8—O2111.53 (14)
O1—C1—O2—C8177.50 (16)N1—C8—O2—C1127.43 (15)
C2—C1—O2—C8−1.67 (18)C7—C8—O2—C13.01 (18)
O1—C1—C2—C7−179.60 (18)O2—C8—N1—C972.79 (19)
O2—C1—C2—C7−0.52 (19)C7—C8—N1—C9−169.91 (14)
O1—C1—C2—C3−2.1 (3)C14—C9—N1—C8−4.3 (2)
O2—C1—C2—C3177.00 (17)C10—C9—N1—C8174.57 (15)
C7—C2—C3—C40.0 (3)N1—C9—C10—C11−177.90 (15)
C1—C2—C3—C4−177.23 (17)C14—C9—C10—C111.0 (2)
C2—C3—C4—C5−0.1 (3)N1—C9—C10—C151.1 (2)
C3—C4—C5—C60.1 (3)C14—C9—C10—C15−179.97 (15)
C4—C5—C6—C70.0 (3)C9—C10—C11—C12−1.2 (2)
C5—C6—C7—C2−0.1 (3)C15—C10—C11—C12179.71 (16)
C5—C6—C7—C8174.15 (19)C10—C11—C12—C130.9 (3)
C3—C2—C7—C60.1 (3)C11—C12—C13—C14−0.4 (3)
C1—C2—C7—C6177.86 (16)C12—C13—C14—C90.3 (3)
C3—C2—C7—C8−175.31 (16)N1—C9—C14—C13178.36 (16)
C1—C2—C7—C82.45 (19)C10—C9—C14—C13−0.5 (2)
C6—C7—C8—N160.0 (3)C11—C10—C15—O3−177.61 (16)
C2—C7—C8—N1−125.16 (15)C9—C10—C15—O33.4 (2)
C6—C7—C8—O2−178.07 (18)C11—C10—C15—O41.8 (2)
C2—C7—C8—O2−3.27 (18)C9—C10—C15—O4−177.24 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O30.86 (2)2.074 (19)2.7004 (18)129.3 (16)
N1—H1···O1i0.86 (2)2.58 (2)3.281 (2)138.9 (15)
O4—H4A···O3ii0.97 (3)1.67 (3)2.6329 (17)174 (2)
C4—H4···O2iii0.93 (2)2.58 (2)3.464 (2)158.9 (17)
C8—H8···O1iv0.983 (18)2.580 (17)3.403 (2)141.4 (12)

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

Footnotes

13-Substituted phthalides. Part XXXIII.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2434).

References

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