2-(3-Oxo-1,3-dihydro-isobenzofuran-1-ylamino)benzoic acid.

In the mol-ecule of the title compound, C(15)H(11)NO(4), the essentially planar phthalide group is oriented at a dihedral angle of 56.78 (5)° with respect to the substituted aromatic ring. An intra-molecular N-H⋯O hydrogen bond results in the formation of a non-planar six-membered ring, which adopts a nearly flattened-boat conformation. In the crystal structure, inter-molecular C-H⋯O, O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules, generating centrosymmetric R(2) (2)(8) and R(2) (2)(11) ring motifs and forming a three-dimensional network.

Related literature

For general background, see: Aoki et al. (1973 ▶, 1974 ▶); Lacova (1973 ▶, 1974 ▶); Elderfield (1951 ▶); Bellasio (1974 ▶, 1975 ▶); Roy & Sarkar (2005 ▶); Kubota & Tatsuno (1971 ▶); Tsi & Tan (1997 ▶). For related structures, see: Büyükgüngör & Odabaşoğlu (2006 ▶); Odabaşoğlu & Büyükgüngör (2006 ▶; 2007 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For ring motif details, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C15H11NO4

M = 269.25

Monoclinic,

a = 7.8135 (6) Å

b = 22.6205 (10) Å

c = 7.0902 (5) Å

β = 101.061 (5)°

V = 1229.88 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.55 × 0.36 × 0.18 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.958, T max = 0.982

12715 measured reflections

2536 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.093

S = 1.07

2536 reflections

225 parameters

All H-atom parameters refined

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800754X/hk2434sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800754X/hk2434Isup2.hkl

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

C15H11NO4	F000 = 560
Mr = 269.25	Dx = 1.454 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12715 reflections
a = 7.8135 (6) Å	θ = 1.8–27.3º
b = 22.6205 (10) Å	µ = 0.11 mm−1
c = 7.0902 (5) Å	T = 296 K
β = 101.061 (5)º	Prism, colorless
V = 1229.88 (14) Å3	0.55 × 0.36 × 0.18 mm
Z = 4

Stoe IPDSII diffractometer	2536 independent reflections
Monochromator: plane graphite	1958 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.034
T = 296 K	θmax = 26.5º
ω scan rotation method	θmin = 1.8º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.958, Tmax = 0.982	k = −28→28
12715 measured reflections	l = −8→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	All H-atom parameters refined
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.2251P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2536 reflections	Δρmax = 0.16 e Å−3
225 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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	0.6576 (2)	0.26649 (7)	0.4899 (2)	0.0402 (4)
C2	0.8303 (2)	0.24430 (7)	0.5812 (2)	0.0367 (4)
C3	0.9781 (3)	0.27532 (8)	0.6650 (3)	0.0457 (4)
C4	1.1272 (3)	0.24364 (9)	0.7337 (3)	0.0518 (5)
C5	1.1279 (3)	0.18248 (9)	0.7191 (3)	0.0511 (5)
C6	0.9805 (2)	0.15141 (8)	0.6356 (3)	0.0460 (4)
C7	0.8308 (2)	0.18333 (7)	0.5662 (2)	0.0354 (4)
C8	0.6571 (2)	0.16362 (7)	0.4548 (3)	0.0364 (4)
C9	0.4218 (2)	0.09230 (6)	0.4534 (2)	0.0332 (4)
C10	0.3436 (2)	0.04653 (6)	0.5436 (2)	0.0321 (3)
C11	0.1982 (2)	0.01723 (7)	0.4399 (3)	0.0396 (4)
C12	0.1264 (2)	0.03208 (8)	0.2541 (3)	0.0458 (4)
C13	0.2021 (2)	0.07689 (8)	0.1666 (3)	0.0435 (4)
C14	0.3465 (2)	0.10673 (7)	0.2628 (2)	0.0389 (4)
C15	0.4117 (2)	0.02788 (6)	0.7427 (2)	0.0334 (3)
N1	0.56924 (19)	0.12145 (6)	0.5475 (2)	0.0387 (3)
O1	0.60404 (19)	0.31643 (5)	0.4713 (2)	0.0563 (4)
O2	0.55684 (15)	0.21973 (5)	0.41990 (18)	0.0437 (3)
O3	0.53512 (17)	0.05196 (5)	0.84778 (17)	0.0457 (3)
O4	0.32808 (17)	−0.01696 (5)	0.80153 (19)	0.0481 (3)
H1	0.596 (2)	0.1184 (8)	0.670 (3)	0.046 (5)*
H3	0.975 (3)	0.3188 (9)	0.671 (3)	0.058 (6)*
H4	1.229 (3)	0.2630 (9)	0.792 (3)	0.060 (6)*
H4A	0.383 (3)	−0.0277 (11)	0.931 (4)	0.094 (9)*
H5	1.233 (3)	0.1623 (8)	0.764 (3)	0.055 (6)*
H6	0.980 (3)	0.1090 (9)	0.626 (3)	0.053 (5)*
H8	0.665 (2)	0.1498 (7)	0.325 (3)	0.036 (4)*
H11	0.149 (2)	−0.0136 (8)	0.506 (3)	0.045 (5)*
H12	0.030 (3)	0.0113 (9)	0.191 (3)	0.055 (6)*
H13	0.154 (2)	0.0893 (8)	0.035 (3)	0.049 (5)*
H14	0.394 (2)	0.1377 (8)	0.199 (3)	0.047 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0518 (10)	0.0365 (8)	0.0337 (9)	−0.0007 (7)	0.0115 (8)	0.0015 (6)
C2	0.0436 (9)	0.0365 (8)	0.0316 (8)	−0.0055 (7)	0.0113 (7)	−0.0002 (6)
C3	0.0524 (11)	0.0441 (10)	0.0421 (10)	−0.0141 (8)	0.0130 (8)	−0.0057 (8)
C4	0.0421 (11)	0.0669 (12)	0.0456 (11)	−0.0212 (10)	0.0068 (9)	−0.0065 (9)
C5	0.0371 (10)	0.0647 (12)	0.0497 (11)	0.0009 (9)	0.0041 (9)	0.0057 (9)
C6	0.0433 (10)	0.0409 (9)	0.0520 (11)	0.0000 (8)	0.0040 (8)	0.0030 (8)
C7	0.0375 (9)	0.0359 (8)	0.0333 (9)	−0.0051 (7)	0.0080 (7)	0.0024 (6)
C8	0.0389 (9)	0.0318 (8)	0.0373 (9)	−0.0013 (7)	0.0040 (7)	0.0031 (6)
C9	0.0321 (8)	0.0308 (7)	0.0361 (9)	0.0020 (6)	0.0044 (7)	−0.0020 (6)
C10	0.0298 (8)	0.0316 (7)	0.0351 (9)	0.0028 (6)	0.0066 (7)	0.0001 (6)
C11	0.0329 (9)	0.0422 (9)	0.0429 (10)	−0.0047 (7)	0.0054 (7)	−0.0011 (7)
C12	0.0366 (10)	0.0522 (10)	0.0448 (11)	−0.0082 (8)	−0.0017 (8)	−0.0046 (8)
C13	0.0426 (10)	0.0487 (10)	0.0351 (10)	0.0033 (8)	−0.0025 (8)	0.0010 (7)
C14	0.0400 (10)	0.0378 (8)	0.0375 (9)	−0.0014 (7)	0.0041 (7)	0.0041 (7)
C15	0.0316 (8)	0.0309 (7)	0.0385 (9)	−0.0003 (6)	0.0089 (7)	−0.0008 (6)
N1	0.0415 (8)	0.0396 (7)	0.0325 (8)	−0.0098 (6)	0.0010 (6)	0.0048 (6)
O1	0.0735 (10)	0.0368 (6)	0.0577 (9)	0.0114 (6)	0.0107 (7)	0.0040 (6)
O2	0.0425 (7)	0.0373 (6)	0.0479 (7)	0.0009 (5)	−0.0001 (6)	0.0049 (5)
O3	0.0525 (8)	0.0435 (6)	0.0369 (7)	−0.0141 (6)	−0.0020 (6)	0.0051 (5)
O4	0.0461 (7)	0.0540 (7)	0.0419 (7)	−0.0159 (6)	0.0028 (6)	0.0113 (6)

O4—H4A	0.97 (3)	C8—O2	1.4872 (18)
N1—H1	0.86 (2)	C8—H8	0.983 (18)
C1—O1	1.203 (2)	C9—N1	1.383 (2)
C1—O2	1.355 (2)	C9—C14	1.405 (2)
C1—C2	1.469 (2)	C9—C10	1.415 (2)
C2—C7	1.383 (2)	C10—C11	1.397 (2)
C2—C3	1.384 (2)	C10—C15	1.472 (2)
C3—C4	1.375 (3)	C11—C12	1.371 (3)
C3—H3	0.98 (2)	C11—H11	0.96 (2)
C4—C5	1.387 (3)	C12—C13	1.380 (3)
C4—H4	0.93 (2)	C12—H12	0.93 (2)
C5—C6	1.382 (3)	C13—C14	1.378 (2)
C5—H5	0.94 (2)	C13—H13	0.98 (2)
C6—C7	1.382 (2)	C14—H14	0.948 (19)
C6—H6	0.963 (19)	C15—O3	1.2271 (19)
C7—C8	1.501 (2)	C15—O4	1.3168 (19)
C8—N1	1.409 (2)
C1—O2—C8	110.76 (12)	N1—C8—C7	115.34 (14)
C15—O4—H4A	109.6 (15)	O2—C8—C7	103.22 (12)
C9—N1—C8	122.22 (14)	N1—C8—H8	110.1 (10)
C9—N1—H1	118.1 (13)	O2—C8—H8	104.0 (10)
C8—N1—H1	118.7 (13)	C7—C8—H8	111.9 (10)
O1—C1—O2	121.82 (16)	N1—C9—C14	120.64 (15)
O1—C1—C2	129.81 (16)	N1—C9—C10	121.49 (14)
O2—C1—C2	108.36 (13)	C14—C9—C10	117.86 (14)
C7—C2—C3	121.61 (16)	C11—C10—C9	119.13 (15)
C7—C2—C1	108.84 (14)	C11—C10—C15	118.49 (14)
C3—C2—C1	129.51 (15)	C9—C10—C15	122.37 (14)
C4—C3—C2	117.92 (17)	C12—C11—C10	122.10 (16)
C4—C3—H3	122.0 (12)	C12—C11—H11	121.2 (11)
C2—C3—H3	120.0 (12)	C10—C11—H11	116.7 (11)
C3—C4—C5	120.56 (18)	C11—C12—C13	118.70 (16)
C3—C4—H4	120.3 (13)	C11—C12—H12	119.0 (12)
C5—C4—H4	119.1 (13)	C13—C12—H12	122.3 (13)
C6—C5—C4	121.62 (19)	C14—C13—C12	121.22 (17)
C6—C5—H5	120.1 (12)	C14—C13—H13	117.3 (11)
C4—C5—H5	118.3 (12)	C12—C13—H13	121.5 (11)
C5—C6—C7	117.75 (17)	C13—C14—C9	120.98 (16)
C5—C6—H6	122.0 (12)	C13—C14—H14	118.8 (11)
C7—C6—H6	120.3 (12)	C9—C14—H14	120.2 (11)
C6—C7—C2	120.54 (16)	O3—C15—O4	121.99 (15)
C6—C7—C8	130.55 (15)	O3—C15—C10	123.52 (14)
C2—C7—C8	108.71 (14)	O4—C15—C10	114.49 (13)
N1—C8—O2	111.53 (14)
O1—C1—O2—C8	177.50 (16)	N1—C8—O2—C1	127.43 (15)
C2—C1—O2—C8	−1.67 (18)	C7—C8—O2—C1	3.01 (18)
O1—C1—C2—C7	−179.60 (18)	O2—C8—N1—C9	72.79 (19)
O2—C1—C2—C7	−0.52 (19)	C7—C8—N1—C9	−169.91 (14)
O1—C1—C2—C3	−2.1 (3)	C14—C9—N1—C8	−4.3 (2)
O2—C1—C2—C3	177.00 (17)	C10—C9—N1—C8	174.57 (15)
C7—C2—C3—C4	0.0 (3)	N1—C9—C10—C11	−177.90 (15)
C1—C2—C3—C4	−177.23 (17)	C14—C9—C10—C11	1.0 (2)
C2—C3—C4—C5	−0.1 (3)	N1—C9—C10—C15	1.1 (2)
C3—C4—C5—C6	0.1 (3)	C14—C9—C10—C15	−179.97 (15)
C4—C5—C6—C7	0.0 (3)	C9—C10—C11—C12	−1.2 (2)
C5—C6—C7—C2	−0.1 (3)	C15—C10—C11—C12	179.71 (16)
C5—C6—C7—C8	174.15 (19)	C10—C11—C12—C13	0.9 (3)
C3—C2—C7—C6	0.1 (3)	C11—C12—C13—C14	−0.4 (3)
C1—C2—C7—C6	177.86 (16)	C12—C13—C14—C9	0.3 (3)
C3—C2—C7—C8	−175.31 (16)	N1—C9—C14—C13	178.36 (16)
C1—C2—C7—C8	2.45 (19)	C10—C9—C14—C13	−0.5 (2)
C6—C7—C8—N1	60.0 (3)	C11—C10—C15—O3	−177.61 (16)
C2—C7—C8—N1	−125.16 (15)	C9—C10—C15—O3	3.4 (2)
C6—C7—C8—O2	−178.07 (18)	C11—C10—C15—O4	1.8 (2)
C2—C7—C8—O2	−3.27 (18)	C9—C10—C15—O4	−177.24 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86 (2)	2.074 (19)	2.7004 (18)	129.3 (16)
N1—H1···O1i	0.86 (2)	2.58 (2)	3.281 (2)	138.9 (15)
O4—H4A···O3ii	0.97 (3)	1.67 (3)	2.6329 (17)	174 (2)
C4—H4···O2iii	0.93 (2)	2.58 (2)	3.464 (2)	158.9 (17)
C8—H8···O1iv	0.983 (18)	2.580 (17)	3.403 (2)	141.4 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86 (2)	2.074 (19)	2.7004 (18)	129.3 (16)
N1—H1⋯O1i	0.86 (2)	2.58 (2)	3.281 (2)	138.9 (15)
O4—H4A⋯O3ii	0.97 (3)	1.67 (3)	2.6329 (17)	174 (2)
C4—H4⋯O2iii	0.93 (2)	2.58 (2)	3.464 (2)	158.9 (17)
C8—H8⋯O1iv	0.983 (18)	2.580 (17)	3.403 (2)	141.4 (12)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .