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

In the title compound, C(15)H(11)NO(4), the dihedral angle formed by the benzene ring and the essentially planar 2-benzofuran ring system is 55.93 (3)°. In the crystal, inter-molecular O-H⋯O hydrogen bonds link pairs of mol-ecules, 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) ▶. 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 ▶).

Experimental

Crystal data

C15H11NO4

M = 269.25

Triclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

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

C15H11NO4	Z = 2
Mr = 269.25	F(000) = 280
Triclinic, P1	Dx = 1.450 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9727 (18) Å	Cell parameters from 3521 reflections
b = 6.987 (2) Å	θ = 2.7–27.8°
c = 15.451 (5) Å	µ = 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

Bruker APEXII CCD diffractometer	2213 independent reflections
Radiation source: fine-focus sealed tube	1971 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 25.2°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.98, Tmax = 0.988	k = −8→8
5940 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-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 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.5514 (2)	1.2253 (2)	0.06142 (9)	0.0419 (3)
C2	0.5971 (2)	1.0142 (2)	0.10724 (9)	0.0380 (3)
C3	0.4306 (2)	0.9320 (2)	0.15965 (10)	0.0413 (3)
H3	0.2840	1.0090	0.1624	0.050*
C4	0.4797 (2)	0.7390 (2)	0.20729 (10)	0.0409 (3)
H4	0.3668	0.6872	0.2422	0.049*
C5	0.6981 (2)	0.62056 (19)	0.20341 (9)	0.0363 (3)
C6	0.8628 (2)	0.6997 (2)	0.14808 (9)	0.0440 (4)
H6	1.0072	0.6210	0.1428	0.053*
C7	0.8119 (3)	0.8932 (2)	0.10154 (9)	0.0443 (4)
H7	0.9235	0.9443	0.0655	0.053*
C8	0.9645 (2)	0.3035 (2)	0.25671 (9)	0.0403 (3)
H8	1.0056	0.2839	0.1965	0.048*
C9	0.9832 (2)	0.10315 (19)	0.31764 (9)	0.0389 (3)
C10	0.8538 (3)	−0.0406 (2)	0.32249 (10)	0.0498 (4)
H10	0.7294	−0.0204	0.2854	0.060*
C11	0.9156 (3)	−0.2158 (2)	0.38446 (11)	0.0581 (4)
H11	0.8300	−0.3144	0.3894	0.070*
C12	1.1024 (3)	−0.2478 (2)	0.43950 (11)	0.0573 (4)
H12	1.1423	−0.3685	0.4795	0.069*
C13	1.2293 (3)	−0.1033 (2)	0.43565 (10)	0.0495 (4)
H13	1.3534	−0.1229	0.4729	0.059*
C14	1.1648 (2)	0.0728 (2)	0.37402 (9)	0.0397 (3)
C15	1.2613 (2)	0.2526 (2)	0.35724 (10)	0.0433 (3)
N1	0.7473 (2)	0.43002 (16)	0.25574 (8)	0.0417 (3)
H1	0.6533	0.4023	0.3003	0.063*
H1A	0.3357	1.4504	0.0381	0.063*
O1	0.35440 (19)	1.33180 (15)	0.06907 (8)	0.0583 (3)
O2	0.7119 (2)	1.29313 (16)	0.01765 (8)	0.0654 (4)
O3	1.14390 (17)	0.38706 (15)	0.29107 (7)	0.0478 (3)
O4	1.41808 (19)	0.28973 (18)	0.39302 (8)	0.0595 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0449 (8)	0.0338 (7)	0.0402 (7)	−0.0024 (6)	0.0006 (6)	0.0019 (6)
C2	0.0421 (7)	0.0327 (7)	0.0344 (7)	−0.0034 (6)	−0.0009 (6)	0.0000 (5)
C3	0.0338 (7)	0.0347 (7)	0.0503 (8)	−0.0015 (6)	−0.0016 (6)	−0.0019 (6)
C4	0.0346 (7)	0.0359 (7)	0.0488 (8)	−0.0088 (6)	0.0014 (6)	0.0006 (6)
C5	0.0402 (7)	0.0292 (7)	0.0368 (7)	−0.0060 (5)	−0.0035 (5)	−0.0006 (5)
C6	0.0398 (8)	0.0375 (8)	0.0440 (8)	0.0031 (6)	0.0058 (6)	0.0033 (6)
C7	0.0433 (8)	0.0399 (8)	0.0399 (7)	−0.0030 (6)	0.0079 (6)	0.0068 (6)
C8	0.0446 (8)	0.0325 (7)	0.0387 (7)	−0.0034 (6)	−0.0005 (6)	−0.0004 (6)
C9	0.0472 (8)	0.0300 (7)	0.0355 (7)	−0.0018 (6)	0.0008 (6)	−0.0040 (5)
C10	0.0656 (10)	0.0345 (7)	0.0491 (8)	−0.0105 (7)	−0.0088 (7)	−0.0058 (6)
C11	0.0833 (12)	0.0326 (8)	0.0593 (10)	−0.0185 (8)	−0.0057 (9)	−0.0037 (7)
C12	0.0818 (12)	0.0324 (8)	0.0495 (9)	−0.0058 (8)	−0.0033 (8)	0.0052 (6)
C13	0.0547 (9)	0.0407 (8)	0.0443 (8)	−0.0007 (7)	−0.0043 (7)	0.0027 (6)
C14	0.0408 (7)	0.0351 (7)	0.0377 (7)	−0.0013 (6)	0.0033 (6)	−0.0025 (6)
C15	0.0363 (7)	0.0413 (8)	0.0451 (8)	−0.0034 (6)	0.0035 (6)	0.0025 (6)
N1	0.0402 (6)	0.0314 (6)	0.0459 (7)	−0.0041 (5)	0.0018 (5)	0.0055 (5)
O1	0.0537 (7)	0.0341 (6)	0.0706 (8)	0.0054 (5)	0.0083 (6)	0.0104 (5)
O2	0.0602 (7)	0.0409 (6)	0.0777 (8)	−0.0019 (5)	0.0204 (6)	0.0142 (6)
O3	0.0423 (6)	0.0378 (5)	0.0561 (6)	−0.0092 (4)	−0.0037 (5)	0.0091 (4)
O4	0.0455 (6)	0.0632 (7)	0.0657 (7)	−0.0194 (5)	−0.0085 (5)	0.0068 (6)

C1—O2	1.2640 (18)	C8—H8	0.9800
C1—O1	1.2670 (17)	C9—C14	1.378 (2)
C1—C2	1.4736 (19)	C9—C10	1.379 (2)
C2—C7	1.389 (2)	C10—C11	1.383 (2)
C2—C3	1.395 (2)	C10—H10	0.9300
C3—C4	1.3755 (19)	C11—C12	1.388 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.395 (2)	C12—C13	1.375 (2)
C4—H4	0.9300	C12—H12	0.9300
C5—N1	1.3884 (17)	C13—C14	1.387 (2)
C5—C6	1.399 (2)	C13—H13	0.9300
C6—C7	1.3729 (19)	C14—C15	1.462 (2)
C6—H6	0.9300	C15—O4	1.2086 (18)
C7—H7	0.9300	C15—O3	1.3476 (17)
C8—N1	1.4054 (18)	N1—H1	0.8837
C8—O3	1.4892 (18)	O1—H1A	0.8551
C8—C9	1.5037 (19)
O2—C1—O1	122.93 (13)	C14—C9—C10	120.58 (13)
O2—C1—C2	118.54 (13)	C14—C9—C8	109.02 (12)
O1—C1—C2	118.52 (12)	C10—C9—C8	130.40 (13)
C7—C2—C3	118.18 (12)	C9—C10—C11	117.69 (15)
C7—C2—C1	120.29 (13)	C9—C10—H10	121.2
C3—C2—C1	121.49 (12)	C11—C10—H10	121.2
C4—C3—C2	121.09 (13)	C10—C11—C12	121.48 (15)
C4—C3—H3	119.5	C10—C11—H11	119.3
C2—C3—H3	119.5	C12—C11—H11	119.3
C3—C4—C5	120.32 (12)	C13—C12—C11	120.85 (14)
C3—C4—H4	119.8	C13—C12—H12	119.6
C5—C4—H4	119.8	C11—C12—H12	119.6
N1—C5—C4	119.29 (12)	C12—C13—C14	117.30 (15)
N1—C5—C6	121.97 (12)	C12—C13—H13	121.3
C4—C5—C6	118.73 (12)	C14—C13—H13	121.3
C7—C6—C5	120.26 (13)	C9—C14—C13	122.06 (14)
C7—C6—H6	119.9	C9—C14—C15	108.59 (12)
C5—C6—H6	119.9	C13—C14—C15	129.34 (14)
C6—C7—C2	121.32 (13)	O4—C15—O3	121.22 (13)
C6—C7—H7	119.3	O4—C15—C14	129.98 (13)
C2—C7—H7	119.3	O3—C15—C14	108.80 (12)
N1—C8—O3	111.92 (11)	C5—N1—C8	122.57 (12)
N1—C8—C9	114.49 (12)	C5—N1—H1	117.3
O3—C8—C9	102.61 (11)	C8—N1—H1	117.7
N1—C8—H8	109.2	C1—O1—H1A	114.1
O3—C8—H8	109.2	C15—O3—C8	110.77 (11)
C9—C8—H8	109.2
O2—C1—C2—C7	−0.4 (2)	C10—C11—C12—C13	1.7 (3)
O1—C1—C2—C7	−179.08 (14)	C11—C12—C13—C14	−0.9 (2)
O2—C1—C2—C3	177.30 (14)	C10—C9—C14—C13	1.9 (2)
O1—C1—C2—C3	−1.3 (2)	C8—C9—C14—C13	−177.47 (13)
C7—C2—C3—C4	2.5 (2)	C10—C9—C14—C15	−176.90 (13)
C1—C2—C3—C4	−175.24 (13)	C8—C9—C14—C15	3.73 (15)
C2—C3—C4—C5	−0.5 (2)	C12—C13—C14—C9	−0.8 (2)
C3—C4—C5—N1	176.53 (13)	C12—C13—C14—C15	177.69 (14)
C3—C4—C5—C6	−2.1 (2)	C9—C14—C15—O4	178.44 (15)
N1—C5—C6—C7	−175.90 (14)	C13—C14—C15—O4	−0.2 (3)
C4—C5—C6—C7	2.7 (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—C6	175.86 (13)	C6—C5—N1—C8	−0.2 (2)
N1—C8—C9—C14	−126.09 (13)	O3—C8—N1—C5	63.86 (17)
O3—C8—C9—C14	−4.61 (14)	C9—C8—N1—C5	−179.92 (12)
N1—C8—C9—C10	54.6 (2)	O4—C15—O3—C8	178.43 (13)
O3—C8—C9—C10	176.11 (14)	C14—C15—O3—C8	−1.89 (15)
C14—C9—C10—C11	−1.1 (2)	N1—C8—O3—C15	127.16 (12)
C8—C9—C10—C11	178.09 (14)	C9—C8—O3—C15	3.93 (14)
C9—C10—C11—C12	−0.6 (3)

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

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) ; (ii) .