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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2579.
Published online 2009 September 30. doi:  10.1107/S1600536809038926
PMCID: PMC2970331

3-[(3-Oxo-1,3-dihydro­isobenzofuran-1-yl)amino]benzoic acid

Abstract

In the title compound, C15H11NO4, the dihedral angle formed by the benzene ring and isobenzofuran ring system is 67.82 (5) Å. The crystal structure is stabilized by inter­molecular O—H(...)O and N—H(...)O hydrogen-bonding inter­actions.

Related literature

For general background to isobenzofuran derivatives, see: Landge et al. (2008 [triangle]); Paradkar et al. (1998 [triangle]); Joseph (1998 [triangle]). Odabaşoğlu & Büyükgüngör (2008 [triangle]).

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Object name is e-65-o2579-scheme1.jpg

Experimental

Crystal data

  • C15H11NO4
  • M r = 269.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2579-efi1.jpg
  • a = 10.9025 (15) Å
  • b = 8.1595 (12) Å
  • c = 14.2654 (18) Å
  • β = 103.463 (1)°
  • V = 1234.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.27 × 0.19 × 0.17 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.972, T max = 0.982
  • 6011 measured reflections
  • 2171 independent reflections
  • 1206 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.107
  • S = 0.90
  • 2171 reflections
  • 181 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038926/bq2162sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038926/bq2162Isup2.hkl

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

Acknowledgments

We acknowledge the financial support of the Natural Science Foundation of China (No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48). This work was also supported by the ‘Students Technology Cultural Innovation Fund’ of Liaocheng University.

supplementary crystallographic information

Comment

Phthalides (isobenzofuran-1(3H)-ones) are well known for their interesting biological properties (Paradkar et al., 1998; Joseph, 1998). In addition, 3-substituted phthalides are vital heterocyclic motifs in many bioactive compounds such as isocoumarins, anthraquinones, anthracyclines, and several alkaloids (Landge et al., 2008). In view of this, various methods have been reported for their synthesis. Herein, the crystal structure of the title compound is presented.

The title compound, (I), (Fig. 1) is a chirality compound with a chiral center at C9. The dihedral angle between the benzene ring and isobenzofuran ring system is 67.82 (5) Å indicating that the two ring systems are not coplanar. The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen-bonding interactions (Fig. 2, Table. 1).

Experimental

To a ethanol solution (30 ml) of 3-aminobenzoic acid (3.00 mmol) added 3.00 mmol 2-formylbenzoic acid. The mixture solution was stirred at 343 K for 2.5 h. Then, sodium ethoxide (6.6 mmol) was added to the reactor and stirring for 0.5 h. Bis(tributyltin)oxide (0.3 mmol) was then added to the reactor and the reaction mixture was stirred for 6 h. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of dichloromethane/methanol (1:1) yielding the title compound unexpectedly. Anal. Calcd (%) for C15H11N1O4 (Mr = 269.25): C, 66.91; H, 4.12; N, 5.20; O, 23.77. Found (%): C, 66.87; H, 4.13; N, 5.21; O, 23.79.

Refinement

All the H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93 (Ar—H), 0.86 (N—H) and 0.82 (O—H) Å.

Figures

Fig. 1.
The asymmetric unit of (I), showing 50% probability displacement ellipsoids.
Fig. 2.
Crystal packing of (I) with hydrogen bonding as dashed lines.

Crystal data

C15H11NO4F(000) = 560
Mr = 269.25Dx = 1.449 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1143 reflections
a = 10.9025 (15) Åθ = 2.7–21.4°
b = 8.1595 (12) ŵ = 0.11 mm1
c = 14.2654 (18) ÅT = 298 K
β = 103.463 (1)°Block, colorless
V = 1234.2 (3) Å30.27 × 0.19 × 0.17 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer2171 independent reflections
Radiation source: fine-focus sealed tube1206 reflections with I > 2σ(I)
graphiteRint = 0.038
[var phi] and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→12
Tmin = 0.972, Tmax = 0.982k = −9→9
6011 measured reflectionsl = −16→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 0.90w = 1/[σ2(Fo2) + (0.0513P)2] where P = (Fo2 + 2Fc2)/3
2171 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.13 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.77236 (15)0.2945 (2)0.94157 (13)0.0511 (5)
H10.75960.24540.88680.061*
O10.99795 (14)0.5570 (2)1.25378 (11)0.0745 (6)
H1A1.02380.60141.30620.112*
O21.19133 (13)0.45300 (19)1.28827 (10)0.0592 (5)
O30.62455 (14)0.2734 (2)1.04292 (10)0.0614 (5)
O40.44272 (16)0.1671 (2)1.06184 (12)0.0788 (6)
C11.0886 (2)0.4649 (3)1.23355 (15)0.0469 (6)
C21.05166 (19)0.3785 (3)1.14008 (14)0.0407 (5)
C30.92786 (18)0.3817 (3)1.08532 (15)0.0425 (5)
H30.86730.44271.10630.051*
C40.89469 (18)0.2949 (3)1.00014 (15)0.0402 (6)
C50.9866 (2)0.2051 (3)0.96999 (16)0.0494 (6)
H50.96560.14780.91210.059*
C61.1080 (2)0.2000 (3)1.02457 (17)0.0522 (6)
H61.16820.13781.00390.063*
C71.1418 (2)0.2860 (3)1.10972 (17)0.0491 (6)
H71.22430.28211.14650.059*
C80.5015 (2)0.2389 (3)1.01183 (17)0.0555 (7)
C90.67070 (19)0.3691 (3)0.96714 (15)0.0478 (6)
H90.69520.47940.99160.057*
C100.55418 (18)0.3801 (3)0.88699 (15)0.0422 (6)
C110.45572 (18)0.3033 (3)0.91465 (15)0.0436 (6)
C120.3365 (2)0.2979 (3)0.85393 (16)0.0558 (7)
H120.27000.24680.87290.067*
C130.3193 (2)0.3700 (3)0.76518 (16)0.0592 (7)
H130.24000.36810.72320.071*
C140.4181 (2)0.4451 (3)0.73746 (16)0.0590 (7)
H140.40420.49260.67660.071*
C150.53674 (19)0.4520 (3)0.79711 (16)0.0514 (6)
H150.60290.50320.77770.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0355 (11)0.0706 (14)0.0439 (11)0.0046 (9)0.0027 (8)−0.0129 (10)
O10.0506 (10)0.1082 (15)0.0594 (11)0.0126 (10)0.0017 (8)−0.0300 (10)
O20.0406 (9)0.0749 (12)0.0529 (10)−0.0040 (8)−0.0077 (7)0.0057 (9)
O30.0450 (10)0.0930 (13)0.0429 (10)0.0050 (9)0.0033 (7)0.0062 (9)
O40.0656 (12)0.1171 (17)0.0559 (11)−0.0037 (10)0.0183 (9)0.0242 (11)
C10.0398 (13)0.0544 (15)0.0446 (14)−0.0052 (12)0.0062 (11)0.0065 (12)
C20.0365 (12)0.0426 (13)0.0410 (13)−0.0027 (10)0.0050 (10)0.0029 (11)
C30.0359 (12)0.0450 (14)0.0450 (13)0.0024 (10)0.0065 (10)−0.0004 (11)
C40.0333 (12)0.0438 (14)0.0412 (13)−0.0018 (10)0.0043 (10)0.0009 (11)
C50.0443 (14)0.0548 (15)0.0499 (15)−0.0004 (12)0.0125 (11)−0.0056 (12)
C60.0403 (14)0.0549 (16)0.0630 (16)0.0059 (11)0.0155 (12)−0.0003 (13)
C70.0329 (13)0.0529 (15)0.0589 (16)0.0003 (11)0.0057 (10)0.0071 (13)
C80.0464 (15)0.0747 (19)0.0448 (15)0.0040 (13)0.0091 (12)0.0034 (13)
C90.0400 (13)0.0575 (15)0.0439 (14)0.0017 (11)0.0058 (10)−0.0028 (12)
C100.0331 (12)0.0499 (14)0.0421 (13)0.0039 (10)0.0054 (10)−0.0064 (11)
C110.0365 (13)0.0559 (15)0.0378 (13)0.0021 (11)0.0075 (10)−0.0010 (11)
C120.0373 (13)0.0786 (19)0.0522 (15)−0.0055 (12)0.0120 (11)−0.0035 (13)
C130.0375 (14)0.0906 (19)0.0448 (15)0.0049 (13)0.0002 (11)−0.0022 (14)
C140.0477 (15)0.0826 (19)0.0454 (14)0.0101 (13)0.0082 (12)0.0117 (14)
C150.0402 (13)0.0630 (16)0.0509 (15)0.0002 (11)0.0108 (11)0.0046 (13)

Geometric parameters (Å, °)

N1—C91.386 (3)C6—C71.377 (3)
N1—C41.399 (2)C6—H60.9300
N1—H10.8600C7—H70.9300
O1—C11.326 (2)C8—C111.458 (3)
O1—H1A0.8200C9—C101.501 (3)
O2—C11.211 (2)C9—H90.9800
O3—C81.341 (3)C10—C111.378 (3)
O3—C91.512 (3)C10—C151.382 (3)
O4—C81.215 (3)C11—C121.384 (3)
C1—C21.479 (3)C12—C131.369 (3)
C2—C71.386 (3)C12—H120.9300
C2—C31.394 (3)C13—C141.375 (3)
C3—C41.380 (3)C13—H130.9300
C3—H30.9300C14—C151.374 (3)
C4—C51.388 (3)C14—H140.9300
C5—C61.371 (3)C15—H150.9300
C5—H50.9300
C9—N1—C4123.46 (18)O4—C8—C11128.4 (2)
C9—N1—H1118.3O3—C8—C11109.5 (2)
C4—N1—H1118.3N1—C9—C10114.38 (18)
C1—O1—H1A109.5N1—C9—O3112.41 (18)
C8—O3—C9110.22 (17)C10—C9—O3102.25 (17)
O2—C1—O1122.0 (2)N1—C9—H9109.2
O2—C1—C2124.1 (2)C10—C9—H9109.2
O1—C1—C2113.96 (17)O3—C9—H9109.2
C7—C2—C3120.0 (2)C11—C10—C15120.71 (18)
C7—C2—C1118.49 (19)C11—C10—C9109.41 (19)
C3—C2—C1121.4 (2)C15—C10—C9129.9 (2)
C4—C3—C2120.3 (2)C10—C11—C12121.0 (2)
C4—C3—H3119.8C10—C11—C8108.61 (18)
C2—C3—H3119.8C12—C11—C8130.3 (2)
C3—C4—C5118.93 (18)C13—C12—C11118.2 (2)
C3—C4—N1123.01 (19)C13—C12—H12120.9
C5—C4—N1118.05 (19)C11—C12—H12120.9
C6—C5—C4120.8 (2)C12—C13—C14120.6 (2)
C6—C5—H5119.6C12—C13—H13119.7
C4—C5—H5119.6C14—C13—H13119.7
C5—C6—C7120.7 (2)C15—C14—C13121.9 (2)
C5—C6—H6119.7C15—C14—H14119.1
C7—C6—H6119.7C13—C14—H14119.1
C6—C7—C2119.3 (2)C14—C15—C10117.6 (2)
C6—C7—H7120.3C14—C15—H15121.2
C2—C7—H7120.3C10—C15—H15121.2
O4—C8—O3122.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···O4i0.821.912.712 (2)166
N1—H1···O2ii0.862.162.956 (2)154

Symmetry codes: (i) −x+3/2, y+1/2, −z+5/2; (ii) x−1/2, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2162).

References

  • Joseph, A. R. (1998). J. Chem. Res. (S), pp. 332–333.
  • Landge, S. M., Berryman, M. & Tör¨k, B. (2008). Tetrahedron Lett.49, 4505–4508.
  • Odabaşoğlu, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o752–o753. [PMC free article] [PubMed]
  • Paradkar, M. V., Ranade, A. A., Kulkarni, M. S., Godbole, H. M. & Joseph, A. R. (1998). J. Chem. Res. (S), pp. 332–333.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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