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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3364
https://doi.org/10.1107/S1600536810048695

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

Chao-Jun Dua*

aSchool of Biology and Chemical Engineering, Nanyang Institute of Technology, Nanyang 473004, People's Republic of China
*Correspondence e-mail: chjdu@yahoo.com.cn

(Received 13 November 2010; accepted 22 November 2010; online 30 November 2010)

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 R22(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)[Odabaşoğlu, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o752-o753.]. For the structure of 3-(3-oxo-1,3-dihydro­isobenzofuran-1-yl­amino)­benzoic acid, see: Li et al. (2009[Li, W., Yin, H., Wen, L., Li, K. & Fan, W. (2009). Acta Cryst. E65, o2579.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C15H11NO4

  • Mr = 269.25

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.98, Tmax = 0.988

  • 5940 measured reflections

  • 2213 independent reflections

  • 1971 reflections with I > 2σ(I)

  • Rint = 0.015
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O4i 0.88 2.11 2.9802 (17) 168
O1—H1A⋯O2ii 0.86 1.79 2.6438 (16) 175
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+3, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048695/lh5161sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048695/lh5161Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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

For related literature, see: Odabaşoğlu & Büyükgüngör (2008).

Experimental top

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 top

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.

Structure description top

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.

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

For related literature, see: Odabaşoğlu & Büyükgüngör (2008).

Computing details top

Data collection: APEX2 (Bruker (2004); cell refinement: SAINT (Bruker (2004); data reduction: SAINT (Bruker (2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.
4-[(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic acid top
Crystal data top
C15H11NO4Z = 2
Mr = 269.25F(000) = 280
Triclinic, P1Dx = 1.450 Mg m−3
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 mm−1
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 top
Bruker APEXII CCD
diffractometer		2213 independent reflections
Radiation source: fine-focus sealed tube1971 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ 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 top
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 = 1.05 w = 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 Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C15H11NO4γ = 77.804 (3)°
Mr = 269.25V = 616.8 (3) Å3
Triclinic, P1Z = 2
a = 5.9727 (18) ÅMo Kα radiation
b = 6.987 (2) ŵ = 0.11 mm−1
c = 15.451 (5) ÅT = 296 K
α = 78.135 (3)°0.21 × 0.16 × 0.11 mm
β = 87.217 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		2213 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1971 reflections with I > 2σ(I)
Tmin = 0.98, Tmax = 0.988Rint = 0.015
5940 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.05Δρmax = 0.21 e Å−3
2213 reflectionsΔρmin = −0.26 e Å−3
182 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 > 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) top
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC15H11NO4
Mr269.25
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)5.9727 (18), 6.987 (2), 15.451 (5)
α, β, γ (°)78.135 (3), 87.217 (3), 77.804 (3)
V (Å3)616.8 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.21 × 0.16 × 0.11
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.98, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		5940, 2213, 1971
Rint0.015
(sin θ/λ)max (Å−1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.101, 1.05
No. of reflections2213
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.26

Computer programs: APEX2 (Bruker (2004), SAINT (Bruker (2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.882.112.9802 (17)168.0
O1—H1A···O2ii0.861.792.6438 (16)174.8
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+3, −z.
 

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3364
https://doi.org/10.1107/S1600536810048695
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