3-[(3-Oxo-1,3-dihydro-isobenzofuran-1-yl)amino]benzoic acid.

In the title compound, C(15)H(11)NO(4), the dihedral angle formed by the benzene ring and isobenzofuran ring system is 67.82 (5) Å. The crystal structure is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen-bonding inter-actions.

Related literature

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

Experimental

Crystal data

C15H11NO4

M = 269.25

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536809038926/bq2162sup1.cif

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

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

C15H11NO4	F(000) = 560
Mr = 269.25	Dx = 1.449 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1143 reflections
a = 10.9025 (15) Å	θ = 2.7–21.4°
b = 8.1595 (12) Å	µ = 0.11 mm−1
c = 14.2654 (18) Å	T = 298 K
β = 103.463 (1)°	Block, colorless
V = 1234.2 (3) Å3	0.27 × 0.19 × 0.17 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	2171 independent reflections
Radiation source: fine-focus sealed tube	1206 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
Tmin = 0.972, Tmax = 0.982	k = −9→9
6011 measured reflections	l = −16→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0513P)2] where P = (Fo2 + 2Fc2)/3
2171 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.77236 (15)	0.2945 (2)	0.94157 (13)	0.0511 (5)
H1	0.7596	0.2454	0.8868	0.061*
O1	0.99795 (14)	0.5570 (2)	1.25378 (11)	0.0745 (6)
H1A	1.0238	0.6014	1.3062	0.112*
O2	1.19133 (13)	0.45300 (19)	1.28827 (10)	0.0592 (5)
O3	0.62455 (14)	0.2734 (2)	1.04292 (10)	0.0614 (5)
O4	0.44272 (16)	0.1671 (2)	1.06184 (12)	0.0788 (6)
C1	1.0886 (2)	0.4649 (3)	1.23355 (15)	0.0469 (6)
C2	1.05166 (19)	0.3785 (3)	1.14008 (14)	0.0407 (5)
C3	0.92786 (18)	0.3817 (3)	1.08532 (15)	0.0425 (5)
H3	0.8673	0.4427	1.1063	0.051*
C4	0.89469 (18)	0.2949 (3)	1.00014 (15)	0.0402 (6)
C5	0.9866 (2)	0.2051 (3)	0.96999 (16)	0.0494 (6)
H5	0.9656	0.1478	0.9121	0.059*
C6	1.1080 (2)	0.2000 (3)	1.02457 (17)	0.0522 (6)
H6	1.1682	0.1378	1.0039	0.063*
C7	1.1418 (2)	0.2860 (3)	1.10972 (17)	0.0491 (6)
H7	1.2243	0.2821	1.1465	0.059*
C8	0.5015 (2)	0.2389 (3)	1.01183 (17)	0.0555 (7)
C9	0.67070 (19)	0.3691 (3)	0.96714 (15)	0.0478 (6)
H9	0.6952	0.4794	0.9916	0.057*
C10	0.55418 (18)	0.3801 (3)	0.88699 (15)	0.0422 (6)
C11	0.45572 (18)	0.3033 (3)	0.91465 (15)	0.0436 (6)
C12	0.3365 (2)	0.2979 (3)	0.85393 (16)	0.0558 (7)
H12	0.2700	0.2468	0.8729	0.067*
C13	0.3193 (2)	0.3700 (3)	0.76518 (16)	0.0592 (7)
H13	0.2400	0.3681	0.7232	0.071*
C14	0.4181 (2)	0.4451 (3)	0.73746 (16)	0.0590 (7)
H14	0.4042	0.4926	0.6766	0.071*
C15	0.53674 (19)	0.4520 (3)	0.79711 (16)	0.0514 (6)
H15	0.6029	0.5032	0.7777	0.062*

	U11	U22	U33	U12	U13	U23
N1	0.0355 (11)	0.0706 (14)	0.0439 (11)	0.0046 (9)	0.0027 (8)	−0.0129 (10)
O1	0.0506 (10)	0.1082 (15)	0.0594 (11)	0.0126 (10)	0.0017 (8)	−0.0300 (10)
O2	0.0406 (9)	0.0749 (12)	0.0529 (10)	−0.0040 (8)	−0.0077 (7)	0.0057 (9)
O3	0.0450 (10)	0.0930 (13)	0.0429 (10)	0.0050 (9)	0.0033 (7)	0.0062 (9)
O4	0.0656 (12)	0.1171 (17)	0.0559 (11)	−0.0037 (10)	0.0183 (9)	0.0242 (11)
C1	0.0398 (13)	0.0544 (15)	0.0446 (14)	−0.0052 (12)	0.0062 (11)	0.0065 (12)
C2	0.0365 (12)	0.0426 (13)	0.0410 (13)	−0.0027 (10)	0.0050 (10)	0.0029 (11)
C3	0.0359 (12)	0.0450 (14)	0.0450 (13)	0.0024 (10)	0.0065 (10)	−0.0004 (11)
C4	0.0333 (12)	0.0438 (14)	0.0412 (13)	−0.0018 (10)	0.0043 (10)	0.0009 (11)
C5	0.0443 (14)	0.0548 (15)	0.0499 (15)	−0.0004 (12)	0.0125 (11)	−0.0056 (12)
C6	0.0403 (14)	0.0549 (16)	0.0630 (16)	0.0059 (11)	0.0155 (12)	−0.0003 (13)
C7	0.0329 (13)	0.0529 (15)	0.0589 (16)	0.0003 (11)	0.0057 (10)	0.0071 (13)
C8	0.0464 (15)	0.0747 (19)	0.0448 (15)	0.0040 (13)	0.0091 (12)	0.0034 (13)
C9	0.0400 (13)	0.0575 (15)	0.0439 (14)	0.0017 (11)	0.0058 (10)	−0.0028 (12)
C10	0.0331 (12)	0.0499 (14)	0.0421 (13)	0.0039 (10)	0.0054 (10)	−0.0064 (11)
C11	0.0365 (13)	0.0559 (15)	0.0378 (13)	0.0021 (11)	0.0075 (10)	−0.0010 (11)
C12	0.0373 (13)	0.0786 (19)	0.0522 (15)	−0.0055 (12)	0.0120 (11)	−0.0035 (13)
C13	0.0375 (14)	0.0906 (19)	0.0448 (15)	0.0049 (13)	0.0002 (11)	−0.0022 (14)
C14	0.0477 (15)	0.0826 (19)	0.0454 (14)	0.0101 (13)	0.0082 (12)	0.0117 (14)
C15	0.0402 (13)	0.0630 (16)	0.0509 (15)	0.0002 (11)	0.0108 (11)	0.0046 (13)

N1—C9	1.386 (3)	C6—C7	1.377 (3)
N1—C4	1.399 (2)	C6—H6	0.9300
N1—H1	0.8600	C7—H7	0.9300
O1—C1	1.326 (2)	C8—C11	1.458 (3)
O1—H1A	0.8200	C9—C10	1.501 (3)
O2—C1	1.211 (2)	C9—H9	0.9800
O3—C8	1.341 (3)	C10—C11	1.378 (3)
O3—C9	1.512 (3)	C10—C15	1.382 (3)
O4—C8	1.215 (3)	C11—C12	1.384 (3)
C1—C2	1.479 (3)	C12—C13	1.369 (3)
C2—C7	1.386 (3)	C12—H12	0.9300
C2—C3	1.394 (3)	C13—C14	1.375 (3)
C3—C4	1.380 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.374 (3)
C4—C5	1.388 (3)	C14—H14	0.9300
C5—C6	1.371 (3)	C15—H15	0.9300
C5—H5	0.9300
C9—N1—C4	123.46 (18)	O4—C8—C11	128.4 (2)
C9—N1—H1	118.3	O3—C8—C11	109.5 (2)
C4—N1—H1	118.3	N1—C9—C10	114.38 (18)
C1—O1—H1A	109.5	N1—C9—O3	112.41 (18)
C8—O3—C9	110.22 (17)	C10—C9—O3	102.25 (17)
O2—C1—O1	122.0 (2)	N1—C9—H9	109.2
O2—C1—C2	124.1 (2)	C10—C9—H9	109.2
O1—C1—C2	113.96 (17)	O3—C9—H9	109.2
C7—C2—C3	120.0 (2)	C11—C10—C15	120.71 (18)
C7—C2—C1	118.49 (19)	C11—C10—C9	109.41 (19)
C3—C2—C1	121.4 (2)	C15—C10—C9	129.9 (2)
C4—C3—C2	120.3 (2)	C10—C11—C12	121.0 (2)
C4—C3—H3	119.8	C10—C11—C8	108.61 (18)
C2—C3—H3	119.8	C12—C11—C8	130.3 (2)
C3—C4—C5	118.93 (18)	C13—C12—C11	118.2 (2)
C3—C4—N1	123.01 (19)	C13—C12—H12	120.9
C5—C4—N1	118.05 (19)	C11—C12—H12	120.9
C6—C5—C4	120.8 (2)	C12—C13—C14	120.6 (2)
C6—C5—H5	119.6	C12—C13—H13	119.7
C4—C5—H5	119.6	C14—C13—H13	119.7
C5—C6—C7	120.7 (2)	C15—C14—C13	121.9 (2)
C5—C6—H6	119.7	C15—C14—H14	119.1
C7—C6—H6	119.7	C13—C14—H14	119.1
C6—C7—C2	119.3 (2)	C14—C15—C10	117.6 (2)
C6—C7—H7	120.3	C14—C15—H15	121.2
C2—C7—H7	120.3	C10—C15—H15	121.2
O4—C8—O3	122.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4i	0.82	1.91	2.712 (2)	166
N1—H1···O2ii	0.86	2.16	2.956 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4i	0.82	1.91	2.712 (2)	166
N1—H1⋯O2ii	0.86	2.16	2.956 (2)	154

Symmetry codes: (i) ; (ii) .