2-(1,3-Dioxoisoindolin-2-yl)propanoic acid.

The crystal structure of the title compound, C(11)H(9)NO(4), consists of infinite one-dimensional polymeric chains due to inter-molecular O-H⋯O hydrogen bonds between the carboxyl-ate and carbonyl groups. The phthalimide ring system and the C-COO group are planar, with r.m.s. deviations of 0.0253 and 0.0067 Å, respectively, from their mean square planes and the dihedral angle between them is 66.41 (7)°. The mol-ecules are stabilized by C=O⋯π inter-actions and weak intra-molecular C-H⋯O hydrogen bonds.

Related literature

For the medicinal properties of isocoumarin, see: Matsuda et al. (1999 ▶). For related crystal structures, see: Li & Liang (2006 ▶); Raza et al. (2009 ▶); Wheeler et al. (2004 ▶). For the graph-set analysis of hydrogen-bond patterns in crystal structures, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H9NO4

M = 219.19

Monoclinic,

a = 9.3056 (8) Å

b = 5.9768 (4) Å

c = 9.7583 (8) Å

β = 110.988 (3)°

V = 506.73 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.30 × 0.25 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.968, T max = 0.974

5705 measured reflections

1381 independent reflections

1302 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.06

1381 reflections

153 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040434/si2209sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040434/si2209Isup2.hkl

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

C11H9NO4	F(000) = 228
Mr = 219.19	Dx = 1.437 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2319 reflections
a = 9.3056 (8) Å	θ = 2.2–28.3°
b = 5.9768 (4) Å	µ = 0.11 mm−1
c = 9.7583 (8) Å	T = 296 K
β = 110.988 (3)°	Prism, colorless
V = 506.73 (7) Å3	0.30 × 0.25 × 0.23 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1381 independent reflections
Radiation source: fine-focus sealed tube	1302 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→7
Tmin = 0.968, Tmax = 0.974	l = −12→13
5705 measured reflections

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.0584P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1381 reflections	Δρmax = 0.16 e Å−3
153 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.132 (13)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.34281 (15)	1.0490 (3)	0.31137 (15)	0.0551 (4)
O2	−0.00322 (14)	0.5031 (3)	0.09136 (15)	0.0520 (4)
O3	0.41497 (15)	0.5761 (3)	0.42520 (15)	0.0550 (5)
O4	0.57532 (16)	0.5164 (5)	0.30695 (19)	0.0817 (7)
N1	0.19830 (14)	0.7462 (3)	0.19714 (14)	0.0358 (4)
C1	0.22202 (19)	0.9473 (3)	0.27082 (17)	0.0382 (4)
C2	0.07493 (19)	1.0033 (3)	0.28948 (17)	0.0402 (5)
C3	0.0385 (3)	1.1806 (4)	0.3606 (2)	0.0562 (6)
C4	−0.1092 (3)	1.1832 (5)	0.3656 (2)	0.0690 (8)
C5	−0.2125 (3)	1.0146 (6)	0.3031 (2)	0.0684 (9)
C6	−0.1755 (2)	0.8353 (5)	0.2313 (2)	0.0539 (6)
C7	−0.02955 (19)	0.8354 (3)	0.22485 (16)	0.0392 (4)
C8	0.04667 (17)	0.6700 (3)	0.16030 (16)	0.0361 (4)
C9	0.31769 (19)	0.6226 (4)	0.1658 (2)	0.0432 (5)
C10	0.45173 (19)	0.5679 (4)	0.3068 (2)	0.0470 (5)
C11	0.3710 (3)	0.7438 (6)	0.0556 (2)	0.0642 (8)
H3	0.10903	1.29359	0.40332	0.0674*
H3A	0.490 (4)	0.564 (6)	0.497 (4)	0.0660*
H4	−0.13859	1.30102	0.41199	0.0828*
H5	−0.30990	1.02072	0.30905	0.0820*
H6	−0.24537	0.72111	0.18964	0.0647*
H9	0.273 (2)	0.482 (5)	0.125 (2)	0.0518*
H11A	0.28411	0.77266	−0.03225	0.0962*
H11B	0.44407	0.65239	0.03244	0.0962*
H11C	0.41850	0.88289	0.09692	0.0962*

	U11	U22	U33	U12	U13	U23
O1	0.0464 (7)	0.0507 (8)	0.0545 (7)	−0.0167 (7)	0.0015 (5)	−0.0070 (7)
O2	0.0474 (7)	0.0484 (8)	0.0563 (7)	−0.0153 (6)	0.0139 (6)	−0.0153 (7)
O3	0.0409 (6)	0.0693 (10)	0.0459 (7)	0.0152 (7)	0.0046 (5)	0.0073 (7)
O4	0.0412 (7)	0.1193 (17)	0.0869 (11)	0.0252 (10)	0.0257 (8)	0.0306 (13)
N1	0.0288 (6)	0.0363 (7)	0.0363 (6)	0.0000 (5)	0.0042 (5)	−0.0024 (6)
C1	0.0385 (8)	0.0368 (8)	0.0310 (7)	−0.0025 (7)	0.0024 (6)	−0.0004 (6)
C2	0.0470 (9)	0.0382 (9)	0.0311 (7)	0.0044 (7)	0.0088 (6)	0.0021 (7)
C3	0.0773 (13)	0.0452 (11)	0.0407 (8)	0.0125 (10)	0.0147 (9)	−0.0034 (8)
C4	0.0893 (16)	0.0758 (17)	0.0461 (10)	0.0356 (15)	0.0293 (10)	0.0019 (11)
C5	0.0612 (12)	0.098 (2)	0.0532 (11)	0.0276 (14)	0.0292 (10)	0.0102 (13)
C6	0.0444 (9)	0.0727 (14)	0.0478 (9)	0.0048 (10)	0.0203 (8)	0.0056 (10)
C7	0.0382 (7)	0.0451 (9)	0.0314 (7)	0.0023 (7)	0.0089 (6)	0.0036 (7)
C8	0.0327 (7)	0.0384 (8)	0.0325 (7)	−0.0032 (7)	0.0060 (5)	0.0005 (6)
C9	0.0346 (8)	0.0473 (10)	0.0444 (8)	0.0009 (8)	0.0102 (6)	−0.0067 (8)
C10	0.0338 (7)	0.0475 (10)	0.0566 (10)	0.0031 (8)	0.0126 (7)	0.0069 (9)
C11	0.0556 (11)	0.0928 (18)	0.0468 (10)	0.0056 (13)	0.0217 (8)	0.0027 (12)

O1—C1	1.213 (2)	C5—C6	1.390 (4)
O2—C8	1.200 (2)	C6—C7	1.382 (3)
O3—C10	1.318 (2)	C7—C8	1.482 (2)
O4—C10	1.190 (3)	C9—C10	1.525 (3)
O3—H3A	0.80 (4)	C9—C11	1.520 (3)
N1—C8	1.402 (2)	C3—H3	0.9300
N1—C9	1.455 (3)	C4—H4	0.9300
N1—C1	1.377 (2)	C5—H5	0.9300
C1—C2	1.482 (3)	C6—H6	0.9300
C2—C3	1.374 (3)	C9—H9	0.96 (3)
C2—C7	1.382 (2)	C11—H11A	0.9600
C3—C4	1.393 (4)	C11—H11B	0.9600
C4—C5	1.375 (4)	C11—H11C	0.9600
O1···O3	3.023 (2)	C5···C11viii	3.551 (3)
O1···C10	3.055 (3)	C6···O4ix	3.283 (3)
O1···C10i	3.268 (3)	C7···O2viii	3.361 (2)
O1···C11	3.177 (3)	C8···O2viii	3.074 (2)
O1···O3ii	2.750 (2)	C8···C3iv	3.534 (3)
O2···C7iii	3.361 (2)	C10···O1	3.055 (3)
O2···N1iii	3.149 (2)	C10···O1iv	3.268 (3)
O2···C3iv	3.168 (3)	C11···C5iii	3.551 (3)
O2···C8iii	3.074 (2)	C11···O1	3.177 (3)
O2···C1iii	3.405 (2)	C1···H3Aii	2.91 (4)
O3···N1	2.615 (2)	C1···H11C	2.9300
O3···O1	3.023 (2)	C2···H4x	3.0100
O3···C1	2.912 (2)	C3···H4x	3.0800
O3···O1v	2.750 (2)	C5···H3x	2.9800
O4···C6vi	3.283 (3)	C5···H11Aviii	2.9200
O1···H3Aii	1.96 (4)	H3···C5xi	2.9800
O1···H11C	2.6300	H3A···O1v	1.96 (4)
O2···H11Aiii	2.8300	H3A···C1v	2.91 (4)
O2···H9	2.48 (2)	H4···O4xii	2.8000
O4···H4vii	2.8000	H4···C2xi	3.0100
O4···H6vi	2.6400	H4···C3xi	3.0800
O4···H11B	2.6400	H6···O4ix	2.6400
N1···O3	2.615 (2)	H9···O2	2.48 (2)
N1···O2viii	3.149 (2)	H11A···O2viii	2.8300
C1···O3	2.912 (2)	H11A···C5iii	2.9200
C1···O2viii	3.405 (2)	H11B···O4	2.6400
C3···C8i	3.534 (3)	H11C···O1	2.6300
C3···O2i	3.168 (3)	H11C···C1	2.9300
C10—O3—H3A	110 (3)	N1—C9—C10	111.01 (15)
C1—N1—C9	124.14 (15)	O3—C10—C9	113.43 (16)
C8—N1—C9	123.75 (16)	O4—C10—C9	122.29 (18)
C1—N1—C8	112.08 (15)	O3—C10—O4	124.24 (19)
O1—C1—C2	129.45 (17)	C2—C3—H3	122.00
N1—C1—C2	106.19 (15)	C4—C3—H3	122.00
O1—C1—N1	124.35 (17)	C3—C4—H4	119.00
C1—C2—C3	129.93 (19)	C5—C4—H4	119.00
C3—C2—C7	122.00 (19)	C4—C5—H5	119.00
C1—C2—C7	108.03 (15)	C6—C5—H5	119.00
C2—C3—C4	116.8 (2)	C5—C6—H6	122.00
C3—C4—C5	121.2 (3)	C7—C6—H6	122.00
C4—C5—C6	121.9 (3)	N1—C9—H9	106.4 (13)
C5—C6—C7	116.6 (2)	C10—C9—H9	106.2 (13)
C2—C7—C6	121.44 (18)	C11—C9—H9	109.1 (12)
C2—C7—C8	108.22 (16)	C9—C11—H11A	109.00
C6—C7—C8	130.30 (18)	C9—C11—H11B	109.00
O2—C8—N1	124.46 (16)	C9—C11—H11C	109.00
O2—C8—C7	130.15 (16)	H11A—C11—H11B	109.00
N1—C8—C7	105.39 (14)	H11A—C11—H11C	109.00
N1—C9—C11	112.0 (2)	H11B—C11—H11C	109.00
C10—C9—C11	111.83 (17)
C8—N1—C1—O1	−178.37 (16)	C1—C2—C7—C6	176.60 (16)
C8—N1—C1—C2	2.54 (18)	C1—C2—C7—C8	−1.21 (18)
C9—N1—C1—O1	3.8 (3)	C3—C2—C7—C6	−1.4 (3)
C9—N1—C1—C2	−175.31 (15)	C3—C2—C7—C8	−179.17 (16)
C1—N1—C8—O2	177.22 (16)	C2—C3—C4—C5	0.5 (3)
C1—N1—C8—C7	−3.24 (18)	C3—C4—C5—C6	−0.5 (4)
C9—N1—C8—O2	−4.9 (3)	C4—C5—C6—C7	−0.4 (3)
C9—N1—C8—C7	174.62 (15)	C5—C6—C7—C2	1.3 (3)
C1—N1—C9—C10	57.8 (2)	C5—C6—C7—C8	178.61 (18)
C1—N1—C9—C11	−67.9 (2)	C2—C7—C8—O2	−177.83 (18)
C8—N1—C9—C10	−119.78 (18)	C2—C7—C8—N1	2.66 (17)
C8—N1—C9—C11	114.5 (2)	C6—C7—C8—O2	4.6 (3)
O1—C1—C2—C3	−2.0 (3)	C6—C7—C8—N1	−174.88 (18)
O1—C1—C2—C7	−179.76 (18)	N1—C9—C10—O3	20.4 (3)
N1—C1—C2—C3	177.02 (18)	N1—C9—C10—O4	−161.9 (3)
N1—C1—C2—C7	−0.73 (18)	C11—C9—C10—O3	146.2 (2)
C1—C2—C3—C4	−177.09 (18)	C11—C9—C10—O4	−36.0 (4)
C7—C2—C3—C4	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1v	0.80 (4)	1.96 (4)	2.750 (2)	172 (4)
C9—H9···O2	0.96 (3)	2.48 (2)	2.899 (2)	106.6 (17)
C8—O2···Cg1iii	1.200 (2)	3.0874 (16)	4.0543 (17)	138.28 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1i	0.80 (4)	1.96 (4)	2.750 (2)	172 (4)
C9—H9⋯O2	0.96 (3)	2.48 (2)	2.899 (2)	106.6 (17)
C8—O2⋯Cg1ii	1.20 (1)	3.09 (1)	4.0543 (17)	138 (1)

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of 5-membered heterocyclic ring.