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

Raza, A.R.; Saddiqa, A.; Tahir, M.N.; Saddiq, S.

doi:10.1107/S1600536811033393

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2435

doi:10.1107/S1600536811033393

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

Abdul Rauf Raza,^a Aisha Saddiqa,^a M. Nawaz Tahir ^b ^* and Sadia Saddiq ^a

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 16 August 2011; accepted 17 August 2011; online 27 August 2011)

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, P 2₁
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[F² > 2σ(F²)] = 0.041
wR(F²) = 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

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) $[-x+1, y+{\script{1\over 2}}, -z]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033393/hb6372sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811033393/hb6372Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Spek, 2009).

Figures top

	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.

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

Crystal data top

C₁₃H₁₃NO₄	F(000) = 260
M_r = 247.24	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0515P)² + 0.0165P] where P = (F_o² + 2F_c²)/3
1635 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₃H₁₃NO₄	V = 629.20 (8) Å³
M_r = 247.24	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.9120 (7) Å	µ = 0.10 mm⁻¹
b = 6.3410 (4) Å	T = 296 K
c = 11.8471 (10) Å	0.34 × 0.26 × 0.24 mm
β = 109.980 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1635 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1267 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.978	R_int = 0.027
5969 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.05	Δρ_max = 0.13 e Å⁻³
1635 reflections	Δρ_min = −0.14 e Å⁻³
166 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) −x+1, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₄
M_r	247.24
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	8.9120 (7), 6.3410 (4), 11.8471 (10)
β (°)	109.980 (4)
V (Å³)	629.20 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.26 × 0.24

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.968, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	5969, 1635, 1267
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.100, 1.05
No. of reflections	1635
No. of parameters	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, former Vice Chancellor, University of Sargodha, Pakistan.

References

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