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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3364.
Published online 2010 November 30. doi:  10.1107/S1600536810048695
PMCID: PMC3011496

4-[(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)amino]­benzoic acid

Abstract

In the title compound, C15H11NO4, the dihedral angle formed by the benzene ring and the essentially planar 2-benzofuran ring system is 55.93 (3)°. In the crystal, inter­molecular O—H(...)O hydrogen bonds link pairs of mol­ecules, generating centrosymmetric R 2 2(8) ring motifs. These dimeric units are connected via N—H(...)O hydrogen bonds, forming C(6) chains along [100].

Related literature

For the structure of 2-(3-oxo-1,3-dihydro­isobenzofuran-1-yl­amino)­benzoic acid, see: Odabaşoğlu & Büyükgüngör (2008) [triangle]. For the structure of 3-(3-oxo-1,3-dihydro­isobenzofuran-1-yl­amino)­benzoic acid, see: Li et al. (2009 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3364-scheme1.jpg

Experimental

Crystal data

  • C15H11NO4
  • M r = 269.25
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3364-efi1.jpg
  • a = 5.9727 (18) Å
  • b = 6.987 (2) Å
  • c = 15.451 (5) Å
  • α = 78.135 (3)°
  • β = 87.217 (3)°
  • γ = 77.804 (3)°
  • V = 616.8 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 296 K
  • 0.21 × 0.16 × 0.11 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.98, T max = 0.988
  • 5940 measured reflections
  • 2213 independent reflections
  • 1971 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.101
  • S = 1.05
  • 2213 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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/S1600536810048695/lh5161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048695/lh5161Isup2.hkl

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

supplementary crystallographic information

Comment

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle formed by the benzene ring and the essentially planar isobenzofuran ring system is 55.93 (3)°. In the crystal, intermolecular O—H···O hydrogen bonds link pairs of molecules, generating centrosymmetric R22(8) ring motifs. These dimeric units are connected via N—H···O hydrogen bonds forming C(6) chains along [100] (see Fig. 2). The crystal structures of 2-(3-oxo-1,3-dihydroisobenzofuran-1-ylamino)benzoic acid (Odabaşoğlu & Büyükgüngör, 2008) and 3-(3-oxo-1,3-dihydroisobenzofuran-1-ylamino)benzoic (Li et al.(2009) have been published previously.

Experimental

4-aminobenzoic acid (5.00 mmol) and 2-formylbenzoic acid (5.00 mmol) were added to an ethanol (35 ml) and DMF (15 ml) mix. The mixture was stirred at 353 K for 5 h. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of DMF/methanol(1:1) yielding the title compound. Anal. yield: ca 98.6%. Single crystals suitable for X-ray analysis were obtained within one week by slow evaporation of a DMF/methanol (1:3) solution of the title compound.

Refinement

All H atoms were placed in idealized positions (C—H = 0.93 or 0.98 Å, N—H = 0.88 Å and O—H = 0.86 Å), and constrained to ride on the atom to which they are bonded, and were included in the refinement in the riding-model approximation. Uiso(H) values were set equal to 1.5Ueq(parent atom) for carboxyl and the secondary amine H atom and to 1.2Ueq(parent atom) for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title compound with 50% probability displacement ellipsoids.
Fig. 2.
Part of the crystal structure with hydrogen bonds shown as dashed lines.

Crystal data

C15H11NO4Z = 2
Mr = 269.25F(000) = 280
Triclinic, P1Dx = 1.450 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9727 (18) ÅCell parameters from 3521 reflections
b = 6.987 (2) Åθ = 2.7–27.8°
c = 15.451 (5) ŵ = 0.11 mm1
α = 78.135 (3)°T = 296 K
β = 87.217 (3)°Block, colorless
γ = 77.804 (3)°0.21 × 0.16 × 0.11 mm
V = 616.8 (3) Å3

Data collection

Bruker APEXII CCD diffractometer2213 independent reflections
Radiation source: fine-focus sealed tube1971 reflections with I > 2σ(I)
graphiteRint = 0.015
[var phi] and ω scansθmax = 25.2°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.98, Tmax = 0.988k = −8→8
5940 measured reflectionsl = −18→18

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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1431P] where P = (Fo2 + 2Fc2)/3
2213 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.26 e Å3

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 > σ(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
C10.5514 (2)1.2253 (2)0.06142 (9)0.0419 (3)
C20.5971 (2)1.0142 (2)0.10724 (9)0.0380 (3)
C30.4306 (2)0.9320 (2)0.15965 (10)0.0413 (3)
H30.28401.00900.16240.050*
C40.4797 (2)0.7390 (2)0.20729 (10)0.0409 (3)
H40.36680.68720.24220.049*
C50.6981 (2)0.62056 (19)0.20341 (9)0.0363 (3)
C60.8628 (2)0.6997 (2)0.14808 (9)0.0440 (4)
H61.00720.62100.14280.053*
C70.8119 (3)0.8932 (2)0.10154 (9)0.0443 (4)
H70.92350.94430.06550.053*
C80.9645 (2)0.3035 (2)0.25671 (9)0.0403 (3)
H81.00560.28390.19650.048*
C90.9832 (2)0.10315 (19)0.31764 (9)0.0389 (3)
C100.8538 (3)−0.0406 (2)0.32249 (10)0.0498 (4)
H100.7294−0.02040.28540.060*
C110.9156 (3)−0.2158 (2)0.38446 (11)0.0581 (4)
H110.8300−0.31440.38940.070*
C121.1024 (3)−0.2478 (2)0.43950 (11)0.0573 (4)
H121.1423−0.36850.47950.069*
C131.2293 (3)−0.1033 (2)0.43565 (10)0.0495 (4)
H131.3534−0.12290.47290.059*
C141.1648 (2)0.0728 (2)0.37402 (9)0.0397 (3)
C151.2613 (2)0.2526 (2)0.35724 (10)0.0433 (3)
N10.7473 (2)0.43002 (16)0.25574 (8)0.0417 (3)
H10.65330.40230.30030.063*
H1A0.33571.45040.03810.063*
O10.35440 (19)1.33180 (15)0.06907 (8)0.0583 (3)
O20.7119 (2)1.29313 (16)0.01765 (8)0.0654 (4)
O31.14390 (17)0.38706 (15)0.29107 (7)0.0478 (3)
O41.41808 (19)0.28973 (18)0.39302 (8)0.0595 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0449 (8)0.0338 (7)0.0402 (7)−0.0024 (6)0.0006 (6)0.0019 (6)
C20.0421 (7)0.0327 (7)0.0344 (7)−0.0034 (6)−0.0009 (6)0.0000 (5)
C30.0338 (7)0.0347 (7)0.0503 (8)−0.0015 (6)−0.0016 (6)−0.0019 (6)
C40.0346 (7)0.0359 (7)0.0488 (8)−0.0088 (6)0.0014 (6)0.0006 (6)
C50.0402 (7)0.0292 (7)0.0368 (7)−0.0060 (5)−0.0035 (5)−0.0006 (5)
C60.0398 (8)0.0375 (8)0.0440 (8)0.0031 (6)0.0058 (6)0.0033 (6)
C70.0433 (8)0.0399 (8)0.0399 (7)−0.0030 (6)0.0079 (6)0.0068 (6)
C80.0446 (8)0.0325 (7)0.0387 (7)−0.0034 (6)−0.0005 (6)−0.0004 (6)
C90.0472 (8)0.0300 (7)0.0355 (7)−0.0018 (6)0.0008 (6)−0.0040 (5)
C100.0656 (10)0.0345 (7)0.0491 (8)−0.0105 (7)−0.0088 (7)−0.0058 (6)
C110.0833 (12)0.0326 (8)0.0593 (10)−0.0185 (8)−0.0057 (9)−0.0037 (7)
C120.0818 (12)0.0324 (8)0.0495 (9)−0.0058 (8)−0.0033 (8)0.0052 (6)
C130.0547 (9)0.0407 (8)0.0443 (8)−0.0007 (7)−0.0043 (7)0.0027 (6)
C140.0408 (7)0.0351 (7)0.0377 (7)−0.0013 (6)0.0033 (6)−0.0025 (6)
C150.0363 (7)0.0413 (8)0.0451 (8)−0.0034 (6)0.0035 (6)0.0025 (6)
N10.0402 (6)0.0314 (6)0.0459 (7)−0.0041 (5)0.0018 (5)0.0055 (5)
O10.0537 (7)0.0341 (6)0.0706 (8)0.0054 (5)0.0083 (6)0.0104 (5)
O20.0602 (7)0.0409 (6)0.0777 (8)−0.0019 (5)0.0204 (6)0.0142 (6)
O30.0423 (6)0.0378 (5)0.0561 (6)−0.0092 (4)−0.0037 (5)0.0091 (4)
O40.0455 (6)0.0632 (7)0.0657 (7)−0.0194 (5)−0.0085 (5)0.0068 (6)

Geometric parameters (Å, °)

C1—O21.2640 (18)C8—H80.9800
C1—O11.2670 (17)C9—C141.378 (2)
C1—C21.4736 (19)C9—C101.379 (2)
C2—C71.389 (2)C10—C111.383 (2)
C2—C31.395 (2)C10—H100.9300
C3—C41.3755 (19)C11—C121.388 (3)
C3—H30.9300C11—H110.9300
C4—C51.395 (2)C12—C131.375 (2)
C4—H40.9300C12—H120.9300
C5—N11.3884 (17)C13—C141.387 (2)
C5—C61.399 (2)C13—H130.9300
C6—C71.3729 (19)C14—C151.462 (2)
C6—H60.9300C15—O41.2086 (18)
C7—H70.9300C15—O31.3476 (17)
C8—N11.4054 (18)N1—H10.8837
C8—O31.4892 (18)O1—H1A0.8551
C8—C91.5037 (19)
O2—C1—O1122.93 (13)C14—C9—C10120.58 (13)
O2—C1—C2118.54 (13)C14—C9—C8109.02 (12)
O1—C1—C2118.52 (12)C10—C9—C8130.40 (13)
C7—C2—C3118.18 (12)C9—C10—C11117.69 (15)
C7—C2—C1120.29 (13)C9—C10—H10121.2
C3—C2—C1121.49 (12)C11—C10—H10121.2
C4—C3—C2121.09 (13)C10—C11—C12121.48 (15)
C4—C3—H3119.5C10—C11—H11119.3
C2—C3—H3119.5C12—C11—H11119.3
C3—C4—C5120.32 (12)C13—C12—C11120.85 (14)
C3—C4—H4119.8C13—C12—H12119.6
C5—C4—H4119.8C11—C12—H12119.6
N1—C5—C4119.29 (12)C12—C13—C14117.30 (15)
N1—C5—C6121.97 (12)C12—C13—H13121.3
C4—C5—C6118.73 (12)C14—C13—H13121.3
C7—C6—C5120.26 (13)C9—C14—C13122.06 (14)
C7—C6—H6119.9C9—C14—C15108.59 (12)
C5—C6—H6119.9C13—C14—C15129.34 (14)
C6—C7—C2121.32 (13)O4—C15—O3121.22 (13)
C6—C7—H7119.3O4—C15—C14129.98 (13)
C2—C7—H7119.3O3—C15—C14108.80 (12)
N1—C8—O3111.92 (11)C5—N1—C8122.57 (12)
N1—C8—C9114.49 (12)C5—N1—H1117.3
O3—C8—C9102.61 (11)C8—N1—H1117.7
N1—C8—H8109.2C1—O1—H1A114.1
O3—C8—H8109.2C15—O3—C8110.77 (11)
C9—C8—H8109.2
O2—C1—C2—C7−0.4 (2)C10—C11—C12—C131.7 (3)
O1—C1—C2—C7−179.08 (14)C11—C12—C13—C14−0.9 (2)
O2—C1—C2—C3177.30 (14)C10—C9—C14—C131.9 (2)
O1—C1—C2—C3−1.3 (2)C8—C9—C14—C13−177.47 (13)
C7—C2—C3—C42.5 (2)C10—C9—C14—C15−176.90 (13)
C1—C2—C3—C4−175.24 (13)C8—C9—C14—C153.73 (15)
C2—C3—C4—C5−0.5 (2)C12—C13—C14—C9−0.8 (2)
C3—C4—C5—N1176.53 (13)C12—C13—C14—C15177.69 (14)
C3—C4—C5—C6−2.1 (2)C9—C14—C15—O4178.44 (15)
N1—C5—C6—C7−175.90 (14)C13—C14—C15—O4−0.2 (3)
C4—C5—C6—C72.7 (2)C9—C14—C15—O3−1.20 (16)
C5—C6—C7—C2−0.7 (2)C13—C14—C15—O3−179.88 (14)
C3—C2—C7—C6−2.0 (2)C4—C5—N1—C8−178.74 (12)
C1—C2—C7—C6175.86 (13)C6—C5—N1—C8−0.2 (2)
N1—C8—C9—C14−126.09 (13)O3—C8—N1—C563.86 (17)
O3—C8—C9—C14−4.61 (14)C9—C8—N1—C5−179.92 (12)
N1—C8—C9—C1054.6 (2)O4—C15—O3—C8178.43 (13)
O3—C8—C9—C10176.11 (14)C14—C15—O3—C8−1.89 (15)
C14—C9—C10—C11−1.1 (2)N1—C8—O3—C15127.16 (12)
C8—C9—C10—C11178.09 (14)C9—C8—O3—C153.93 (14)
C9—C10—C11—C12−0.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.882.112.9802 (17)168
O1—H1A···O2ii0.861.792.6438 (16)175

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5161).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, W., Yin, H., Wen, L., Li, K. & Fan, W. (2009). Acta Cryst. E65, o2579. [PMC free article] [PubMed]
  • Odabaşoğlu, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o752–o753. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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