(2R)-2-(1,3-Dioxoisoindolin-2-yl)-3-methyl­butanoic acid

Abstract

In the title compound, C₁₃H₁₃NO₄, the dihedral angle between the nine-membered phthalimino ring system and the carb­oxy­lic acid group is 67.15 (9)°. An intra­molecular C—H⋯O close contact, which forms an S(6) ring, may help to establish the mol­ecular conformation. In the crystal, mol­ecules 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 _r = 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) ų

• 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

• Δρ_max = 0.13 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

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

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) .

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) is being submitted as a part of our research work to synthesize different compounds of phthalic anhydride and various amino acids. In this context, we have reported the crystal structure of (II) i.e., (2R)-2-(1,3-dioxoisoindolin-2-yl)-4-(methylsulfanyl)butanoic acid (Raza et al., 2009). The crystal structure of (III) i.e., 2-phthaliminoethanoic acid (Barooah, et al., 2006) has also been published which is related to (I).

In (I), the group A (C1–C8/N1/O1/O2) of 1H-isoindole-1,3(2H)- dione moiety and the group B (C9/C10/O3/O4) of valine are almost planar with r.m.s. deviations of 0.011 and 0.005 Å, respectively. The propane group C (C11/C12/C13) of valine is of course planar. The dihedral angle between A/B, A/C and B/C is 67.15 (9), 54.87 (30) and 51.52 (22)°, respectively. There exist intramolecular H-bondings of C—H···O type (Table 1, Fig. 1) completing S(6) ring motif (Bernstein et al., 1995). The molecules are stabilized in the form of infinite one dimensional polymeric chains along the b axis due to intermolecular hydrogen bonds of the O—H···O type (Table 1, Fig. 2). There does not exist any kind of significant π interaction.

Experimental

Valine (1.57 g, 13.4 mmol) and phthalic anhydride (2.13 g, 14.38 mmol) were added to a flask with constant stirring at 423 K for 2 h. The reaction mixture was brought to room temperature and the crystalline phthallic anhydride on the walls of the flask were removed. The solid crude product was purified by crystallization from ethanol:water (7:3) that afforded light blue prisms of the title compound (I).

Refinement

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. The H-atoms were positioned geometrically with (O–H = 0.82, C–H = 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = xU_eq(C, O), where x = 1.5 for hydroxy & methyl H-atoms and x = 1.2 for other H-atoms.

Figures

Fig. 1.

View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted line indicates the intramolecular H-bond.

Fig. 2.

The partial packing, which shows that molecules form one dimensional polymeric network parallel extending along the b axis.

Crystal data

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

Data collection

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

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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)

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 codes: (i) −x+1, y+1/2, −z.