(2R)-2-(1,3-Dioxoisoindolin-2-yl)-3-methyl-butanoic acid.

In the title compound, C(13)H(13)NO(4), the dihedral angle between the nine-membered phthalimino ring system and the carb-oxy-lic acid group is 67.15 (9)°. An intra-molecular C-H⋯O close contact, which forms an S(6) ring, may help to establish the mol-ecular conformation. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, thereby forming C(7) chains propagating in [010].

Related literature

For related structures, see: Barooah et al. (2006 ▶); Raza et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H13NO4

M = 247.24

Monoclinic,

a = 8.9120 (7) Å

b = 6.3410 (4) Å

c = 11.8471 (10) Å

β = 109.980 (4)°

V = 629.20 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.34 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.968, T max = 0.978

5969 measured reflections

1635 independent reflections

1267 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.100

S = 1.05

1635 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811033393/hb6372sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033393/hb6372Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033393/hb6372Isup3.cml

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

C13H13NO4	F(000) = 260
Mr = 247.24	Dx = 1.305 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1267 reflections
a = 8.9120 (7) Å	θ = 2.5–27.9°
b = 6.3410 (4) Å	µ = 0.10 mm−1
c = 11.8471 (10) Å	T = 296 K
β = 109.980 (4)°	Prism, light blue
V = 629.20 (8) Å3	0.34 × 0.26 × 0.24 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1635 independent reflections
Radiation source: fine-focus sealed tube	1267 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 7.7 pixels mm-1	θmax = 27.9°, θmin = 2.5°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.968, Tmax = 0.978	l = −15→15
5969 measured reflections

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) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.0165P] where P = (Fo2 + 2Fc2)/3
1635 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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	0.63294 (18)	0.2169 (3)	0.16180 (14)	0.0529 (5)
O2	1.0337 (2)	0.6899 (4)	0.31913 (18)	0.0733 (7)
O3	0.60132 (17)	0.6706 (3)	0.05589 (13)	0.0577 (6)
O4	0.4167 (2)	0.6777 (4)	0.14255 (16)	0.0743 (8)
N1	0.80699 (19)	0.4850 (3)	0.24640 (16)	0.0428 (6)
C1	0.7654 (3)	0.2944 (3)	0.18945 (19)	0.0411 (7)
C2	0.9110 (3)	0.2094 (4)	0.17135 (19)	0.0441 (7)
C3	0.9340 (3)	0.0270 (4)	0.1157 (2)	0.0582 (9)
C4	1.0854 (4)	−0.0072 (6)	0.1117 (3)	0.0743 (11)
C5	1.2072 (4)	0.1337 (6)	0.1601 (3)	0.0749 (13)
C6	1.1836 (3)	0.3191 (5)	0.2150 (3)	0.0651 (10)
C7	1.0331 (3)	0.3524 (4)	0.2200 (2)	0.0483 (8)
C8	0.9695 (3)	0.5322 (4)	0.2691 (2)	0.0482 (8)
C9	0.6940 (3)	0.6354 (4)	0.2664 (2)	0.0475 (7)
C10	0.5531 (3)	0.6619 (4)	0.1499 (2)	0.0474 (8)
C11	0.6453 (4)	0.5844 (5)	0.3757 (2)	0.0649 (10)
C12	0.7868 (4)	0.5100 (9)	0.4803 (3)	0.1015 (18)
C13	0.5689 (5)	0.7743 (7)	0.4111 (3)	0.113 (2)
H3	0.85144	−0.06851	0.08244	0.0699*
H3A	0.52335	0.67521	−0.00594	0.0866*
H4	1.10506	−0.12888	0.07523	0.0890*
H5	1.30763	0.10496	0.15619	0.0897*
H6	1.26560	0.41595	0.24673	0.0782*
H9	0.74879	0.77181	0.28290	0.0570*
H11	0.56633	0.47043	0.35343	0.0778*
H12A	0.87100	0.61231	0.49703	0.1522*
H12B	0.82370	0.37748	0.46052	0.1522*
H12C	0.75565	0.49291	0.54970	0.1522*
H13A	0.64598	0.88579	0.43682	0.1699*
H13B	0.53183	0.73678	0.47557	0.1699*
H13C	0.48032	0.82095	0.34336	0.1699*

	U11	U22	U33	U12	U13	U23
O1	0.0399 (8)	0.0645 (10)	0.0516 (9)	−0.0117 (8)	0.0123 (7)	−0.0078 (9)
O2	0.0627 (11)	0.0696 (12)	0.0762 (12)	−0.0232 (11)	0.0090 (9)	−0.0166 (12)
O3	0.0446 (9)	0.0857 (14)	0.0411 (8)	0.0087 (10)	0.0125 (6)	0.0097 (10)
O4	0.0454 (10)	0.1094 (17)	0.0700 (12)	0.0175 (12)	0.0223 (8)	0.0094 (13)
N1	0.0363 (10)	0.0467 (10)	0.0405 (9)	0.0011 (9)	0.0067 (7)	−0.0027 (8)
C1	0.0395 (12)	0.0453 (12)	0.0350 (11)	−0.0019 (10)	0.0082 (9)	0.0017 (10)
C2	0.0435 (11)	0.0503 (12)	0.0389 (11)	0.0056 (11)	0.0148 (9)	0.0077 (11)
C3	0.0675 (16)	0.0585 (16)	0.0540 (15)	0.0075 (13)	0.0276 (12)	0.0010 (12)
C4	0.090 (2)	0.075 (2)	0.0713 (19)	0.027 (2)	0.0449 (17)	0.0102 (17)
C5	0.0615 (18)	0.102 (3)	0.0733 (19)	0.0265 (19)	0.0387 (15)	0.024 (2)
C6	0.0426 (14)	0.089 (2)	0.0635 (16)	−0.0001 (14)	0.0179 (12)	0.0150 (16)
C7	0.0373 (12)	0.0646 (16)	0.0406 (12)	0.0017 (11)	0.0102 (9)	0.0093 (11)
C8	0.0397 (12)	0.0545 (15)	0.0425 (12)	−0.0060 (11)	0.0039 (10)	0.0036 (11)
C9	0.0494 (13)	0.0479 (13)	0.0441 (12)	0.0053 (11)	0.0146 (10)	−0.0039 (11)
C10	0.0455 (13)	0.0529 (14)	0.0445 (12)	0.0078 (11)	0.0164 (9)	0.0022 (11)
C11	0.0712 (18)	0.081 (2)	0.0475 (14)	0.0195 (15)	0.0266 (13)	0.0049 (13)
C12	0.104 (3)	0.153 (4)	0.0490 (17)	0.039 (3)	0.0281 (16)	0.029 (2)
C13	0.155 (4)	0.126 (4)	0.076 (2)	0.062 (3)	0.062 (2)	0.003 (2)

O1—C1	1.216 (3)	C9—C10	1.525 (3)
O2—C8	1.203 (3)	C9—C11	1.534 (4)
O3—C10	1.325 (3)	C11—C12	1.510 (5)
O4—C10	1.193 (3)	C11—C13	1.512 (6)
O3—H3A	0.8200	C3—H3	0.9300
N1—C8	1.412 (3)	C4—H4	0.9300
N1—C9	1.464 (3)	C5—H5	0.9300
N1—C1	1.372 (3)	C6—H6	0.9300
C1—C2	1.487 (4)	C9—H9	0.9800
C2—C3	1.381 (4)	C11—H11	0.9800
C2—C7	1.382 (4)	C12—H12A	0.9600
C3—C4	1.383 (5)	C12—H12B	0.9600
C4—C5	1.371 (5)	C12—H12C	0.9600
C5—C6	1.394 (5)	C13—H13A	0.9600
C6—C7	1.379 (4)	C13—H13B	0.9600
C7—C8	1.478 (4)	C13—H13C	0.9600
C10—O3—H3A	109.00	C9—C11—C12	111.1 (3)
C1—N1—C9	124.6 (2)	C2—C3—H3	122.00
C8—N1—C9	123.3 (2)	C4—C3—H3	122.00
C1—N1—C8	111.6 (2)	C3—C4—H4	119.00
O1—C1—C2	129.0 (2)	C5—C4—H4	119.00
N1—C1—C2	106.7 (2)	C4—C5—H5	119.00
O1—C1—N1	124.3 (2)	C6—C5—H5	119.00
C1—C2—C7	107.7 (2)	C5—C6—H6	122.00
C3—C2—C7	121.6 (3)	C7—C6—H6	122.00
C1—C2—C3	130.7 (2)	N1—C9—H9	107.00
C2—C3—C4	117.0 (3)	C10—C9—H9	106.00
C3—C4—C5	121.7 (3)	C11—C9—H9	106.00
C4—C5—C6	121.4 (3)	C9—C11—H11	108.00
C5—C6—C7	117.0 (3)	C12—C11—H11	108.00
C2—C7—C8	108.5 (2)	C13—C11—H11	108.00
C6—C7—C8	130.1 (3)	C11—C12—H12A	109.00
C2—C7—C6	121.4 (3)	C11—C12—H12B	109.00
O2—C8—N1	123.7 (2)	C11—C12—H12C	109.00
O2—C8—C7	130.8 (3)	H12A—C12—H12B	109.00
N1—C8—C7	105.5 (2)	H12A—C12—H12C	110.00
N1—C9—C10	108.94 (19)	H12B—C12—H12C	109.00
N1—C9—C11	114.1 (2)	C11—C13—H13A	109.00
C10—C9—C11	113.8 (2)	C11—C13—H13B	109.00
O3—C10—C9	111.2 (2)	C11—C13—H13C	109.00
O4—C10—C9	125.4 (2)	H13A—C13—H13B	109.00
O3—C10—O4	123.4 (2)	H13A—C13—H13C	109.00
C9—C11—C13	110.5 (3)	H13B—C13—H13C	109.00
C12—C11—C13	110.5 (3)
C8—N1—C1—O1	178.8 (2)	C3—C2—C7—C6	0.0 (4)
C8—N1—C1—C2	−0.8 (2)	C3—C2—C7—C8	178.3 (2)
C9—N1—C1—O1	−9.3 (3)	C2—C3—C4—C5	−0.3 (4)
C9—N1—C1—C2	171.12 (19)	C3—C4—C5—C6	−0.4 (5)
C1—N1—C8—O2	−179.3 (2)	C4—C5—C6—C7	1.0 (5)
C1—N1—C8—C7	0.5 (2)	C5—C6—C7—C2	−0.8 (4)
C9—N1—C8—O2	8.7 (4)	C5—C6—C7—C8	−178.6 (3)
C9—N1—C8—C7	−171.57 (19)	C2—C7—C8—O2	179.8 (3)
C1—N1—C9—C10	−46.8 (3)	C2—C7—C8—N1	0.1 (3)
C1—N1—C9—C11	81.6 (3)	C6—C7—C8—O2	−2.2 (5)
C8—N1—C9—C10	124.2 (2)	C6—C7—C8—N1	178.1 (3)
C8—N1—C9—C11	−107.4 (3)	N1—C9—C10—O3	−41.0 (3)
O1—C1—C2—C3	2.6 (4)	N1—C9—C10—O4	140.5 (3)
O1—C1—C2—C7	−178.8 (2)	C11—C9—C10—O3	−169.6 (2)
N1—C1—C2—C3	−177.8 (2)	C11—C9—C10—O4	12.0 (4)
N1—C1—C2—C7	0.8 (2)	N1—C9—C11—C12	40.7 (4)
C1—C2—C3—C4	179.0 (3)	N1—C9—C11—C13	163.8 (3)
C7—C2—C3—C4	0.5 (4)	C10—C9—C11—C12	166.6 (3)
C1—C2—C7—C6	−178.8 (2)	C10—C9—C11—C13	−70.4 (3)
C1—C2—C7—C8	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1i	0.82	1.91	2.723 (2)	169
C13—H13C···O4	0.96	2.43	3.064 (4)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1i	0.82	1.91	2.723 (2)	169
C13—H13C⋯O4	0.96	2.43	3.064 (4)	124

Symmetry code: (i) .