organic compounds
(2R)-2-(1,3-Dioxoisoindolin-2-yl)-4-(methylsulfanyl)butanoic acid
aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and cDepartment of Chemistry, Government College University, Lahore, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
The title compound, C13H13NO4S, the 1,3-dioxoisoindolin-2-yl unit is planar (r.m.s. deviation 0.0192 Å) and is oriented at a dihedral angle of 79.14 (18)° to the carboxylate group. An intramolecular C—H⋯O hydrogen bond leads to the formation of a planar (r.m.s. deviation 0.0419 Å)R(5) ring motif. In the crystal, molecules are connected through O—H⋯O and C—H⋯O hydrogen bonds with R22(9) ring motifs into chains extending along the b axis.
Related literature
For the biological activity of isocoumarin and 3,4-dihydroisocoumarin, see: Hill (1986); Canedo et al. (1997); Whyte et al. (1996). For related structures, see: Barooah et al. (2007); Feeder & Jones (1994); Rajagopal et al. (2003). For graph-set motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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.
Supporting information
10.1107/S1600536809028992/pb2001sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809028992/pb2001Isup2.hkl
The methionine (2.0 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 colorless prisms of the title compound (I).
Yield 81%.
All the Friedal pairs were merged.
H atoms (for hydroxy and methine) were located in a difference Fourier map and their coordinates were refined. The remaining H atoms were positioned geometrically with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, respectively and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).C13H13NO4S | F(000) = 584 |
Mr = 279.30 | Dx = 1.365 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1864 reflections |
a = 6.7923 (6) Å | θ = 2.3–28.0° |
b = 9.9581 (8) Å | µ = 0.25 mm−1 |
c = 20.0970 (17) Å | T = 296 K |
V = 1359.3 (2) Å3 | Prismatic, colorless |
Z = 4 | 0.20 × 0.14 × 0.10 mm |
Bruker Kappa APEXII CCD diffractometer | 1864 independent reflections |
Radiation source: fine-focus sealed tube | 1679 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 7.50 pixels mm-1 | θmax = 28.0°, θmin = 2.3° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −12→7 |
Tmin = 0.969, Tmax = 0.985 | l = −23→26 |
7865 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.057P)2 + 0.2154P] where P = (Fo2 + 2Fc2)/3 |
1864 reflections | (Δ/σ)max < 0.001 |
179 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C13H13NO4S | V = 1359.3 (2) Å3 |
Mr = 279.30 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.7923 (6) Å | µ = 0.25 mm−1 |
b = 9.9581 (8) Å | T = 296 K |
c = 20.0970 (17) Å | 0.20 × 0.14 × 0.10 mm |
Bruker Kappa APEXII CCD diffractometer | 1864 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1679 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.985 | Rint = 0.024 |
7865 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.20 e Å−3 |
1864 reflections | Δρmin = −0.33 e Å−3 |
179 parameters |
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 esds 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 | ||
S1 | −0.16661 (11) | 0.67441 (7) | 0.42200 (3) | 0.0592 (2) | |
O1 | 0.3364 (3) | 0.2322 (2) | 0.26744 (9) | 0.0561 (6) | |
O2 | 0.3978 (3) | 0.3163 (2) | 0.36803 (8) | 0.0651 (7) | |
O3 | 0.3730 (2) | 0.55141 (18) | 0.23747 (8) | 0.0475 (5) | |
O4 | −0.2132 (3) | 0.3346 (2) | 0.21563 (10) | 0.0656 (7) | |
N1 | 0.0832 (3) | 0.43417 (17) | 0.24261 (8) | 0.0355 (5) | |
C1 | 0.2192 (3) | 0.5168 (2) | 0.21199 (11) | 0.0361 (6) | |
C2 | 0.1381 (4) | 0.5487 (2) | 0.14518 (10) | 0.0390 (6) | |
C3 | 0.2158 (5) | 0.6255 (3) | 0.09427 (12) | 0.0543 (8) | |
C4 | 0.1055 (5) | 0.6347 (3) | 0.03591 (13) | 0.0638 (9) | |
C5 | −0.0735 (6) | 0.5715 (3) | 0.03025 (14) | 0.0668 (9) | |
C6 | −0.1514 (5) | 0.4944 (3) | 0.08144 (13) | 0.0594 (8) | |
C7 | −0.0415 (4) | 0.4844 (2) | 0.13909 (11) | 0.0430 (6) | |
C8 | −0.0790 (3) | 0.4072 (2) | 0.20120 (11) | 0.0422 (7) | |
C9 | 0.1029 (3) | 0.3829 (2) | 0.31004 (10) | 0.0358 (6) | |
C10 | 0.0710 (3) | 0.4911 (2) | 0.36262 (11) | 0.0423 (6) | |
C11 | −0.1370 (4) | 0.5462 (3) | 0.36027 (11) | 0.0465 (7) | |
C12 | −0.4193 (6) | 0.7176 (4) | 0.40992 (18) | 0.0927 (14) | |
C13 | 0.2982 (3) | 0.3089 (2) | 0.31883 (11) | 0.0412 (6) | |
H1 | 0.435 (5) | 0.196 (3) | 0.2742 (16) | 0.0673* | |
H3 | 0.33622 | 0.66910 | 0.09873 | 0.0652* | |
H4 | 0.15390 | 0.68438 | 0.00030 | 0.0764* | |
H5 | −0.14459 | 0.58059 | −0.00904 | 0.0801* | |
H6 | −0.27220 | 0.45141 | 0.07712 | 0.0713* | |
H9 | 0.002 (4) | 0.316 (3) | 0.3151 (12) | 0.0430* | |
H10A | 0.09595 | 0.45360 | 0.40636 | 0.0507* | |
H10B | 0.16374 | 0.56373 | 0.35543 | 0.0507* | |
H11A | −0.23038 | 0.47436 | 0.36834 | 0.0558* | |
H11B | −0.16321 | 0.58325 | 0.31651 | 0.0558* | |
H12A | −0.43704 | 0.75226 | 0.36576 | 0.1385* | |
H12B | −0.45705 | 0.78452 | 0.44181 | 0.1385* | |
H12C | −0.49950 | 0.63905 | 0.41568 | 0.1385* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0668 (4) | 0.0560 (3) | 0.0549 (4) | 0.0046 (3) | 0.0121 (3) | −0.0137 (3) |
O1 | 0.0542 (10) | 0.0646 (11) | 0.0494 (10) | 0.0238 (9) | −0.0114 (9) | −0.0182 (9) |
O2 | 0.0685 (11) | 0.0852 (14) | 0.0417 (9) | 0.0298 (11) | −0.0157 (8) | −0.0100 (9) |
O3 | 0.0448 (8) | 0.0545 (9) | 0.0432 (9) | −0.0130 (8) | −0.0076 (7) | 0.0070 (7) |
O4 | 0.0510 (10) | 0.0801 (13) | 0.0656 (12) | −0.0252 (10) | −0.0100 (9) | 0.0065 (11) |
N1 | 0.0360 (8) | 0.0381 (8) | 0.0323 (8) | −0.0015 (8) | −0.0004 (7) | 0.0012 (7) |
C1 | 0.0399 (10) | 0.0326 (9) | 0.0359 (10) | 0.0005 (8) | 0.0000 (8) | −0.0018 (8) |
C2 | 0.0508 (12) | 0.0346 (9) | 0.0315 (10) | 0.0027 (9) | −0.0023 (9) | −0.0029 (8) |
C3 | 0.0728 (17) | 0.0508 (12) | 0.0394 (12) | −0.0090 (12) | −0.0011 (12) | 0.0059 (10) |
C4 | 0.097 (2) | 0.0591 (14) | 0.0353 (12) | −0.0061 (16) | −0.0088 (14) | 0.0057 (11) |
C5 | 0.100 (2) | 0.0601 (15) | 0.0404 (13) | 0.0027 (17) | −0.0261 (15) | 0.0002 (12) |
C6 | 0.0686 (16) | 0.0573 (13) | 0.0524 (14) | −0.0024 (14) | −0.0235 (14) | −0.0051 (12) |
C7 | 0.0502 (12) | 0.0398 (10) | 0.0391 (11) | 0.0021 (10) | −0.0066 (10) | −0.0046 (9) |
C8 | 0.0398 (11) | 0.0440 (11) | 0.0427 (12) | −0.0016 (9) | −0.0058 (9) | −0.0035 (9) |
C9 | 0.0382 (10) | 0.0369 (10) | 0.0324 (10) | 0.0002 (9) | 0.0022 (8) | 0.0020 (8) |
C10 | 0.0460 (12) | 0.0467 (11) | 0.0342 (10) | 0.0049 (10) | 0.0008 (9) | −0.0039 (9) |
C11 | 0.0494 (12) | 0.0517 (12) | 0.0383 (11) | 0.0096 (11) | 0.0036 (10) | −0.0045 (10) |
C12 | 0.089 (2) | 0.111 (3) | 0.078 (2) | 0.053 (2) | 0.0201 (19) | −0.001 (2) |
C13 | 0.0466 (11) | 0.0424 (10) | 0.0347 (10) | 0.0074 (10) | 0.0002 (9) | 0.0013 (9) |
S1—C11 | 1.792 (3) | C7—C8 | 1.488 (3) |
S1—C12 | 1.786 (4) | C9—C13 | 1.528 (3) |
O1—C13 | 1.311 (3) | C9—C10 | 1.525 (3) |
O2—C13 | 1.200 (3) | C10—C11 | 1.516 (3) |
O3—C1 | 1.213 (3) | C3—H3 | 0.9300 |
O4—C8 | 1.199 (3) | C4—H4 | 0.9300 |
O1—H1 | 0.77 (3) | C5—H5 | 0.9300 |
N1—C8 | 1.407 (3) | C6—H6 | 0.9300 |
N1—C9 | 1.454 (3) | C9—H9 | 0.96 (3) |
N1—C1 | 1.382 (3) | C10—H10A | 0.9700 |
C1—C2 | 1.486 (3) | C10—H10B | 0.9700 |
C2—C7 | 1.383 (4) | C11—H11A | 0.9700 |
C2—C3 | 1.382 (3) | C11—H11B | 0.9700 |
C3—C4 | 1.395 (4) | C12—H12A | 0.9600 |
C4—C5 | 1.374 (5) | C12—H12B | 0.9600 |
C5—C6 | 1.389 (4) | C12—H12C | 0.9600 |
C6—C7 | 1.382 (4) | ||
S1···C7i | 3.610 (2) | C10···O3 | 3.301 (3) |
S1···H5ii | 3.1600 | C11···C8 | 3.506 (3) |
S1···H12Biii | 3.1100 | C13···O3 | 2.960 (3) |
O1···N1 | 2.693 (3) | C1···H1vi | 2.96 (3) |
O1···C1 | 3.148 (3) | C1···H10B | 2.9400 |
O1···O3iv | 2.673 (3) | C2···H9i | 2.94 (3) |
O2···C4v | 3.409 (3) | C3···H9i | 3.02 (3) |
O2···C3iv | 3.328 (4) | C8···H11B | 2.9600 |
O3···C13 | 2.960 (3) | H1···O3iv | 1.96 (3) |
O3···C10 | 3.301 (3) | H1···C1iv | 2.96 (3) |
O3···O4i | 3.165 (3) | H3···O2vi | 2.4200 |
O3···O1vi | 2.673 (3) | H4···O2viii | 2.6800 |
O4···O3vii | 3.165 (3) | H5···S1ix | 3.1600 |
O1···H12Avii | 2.7700 | H6···H12Bx | 2.5100 |
O1···H11Bvii | 2.5400 | H9···O4 | 2.48 (3) |
O2···H3iv | 2.4200 | H9···H11A | 2.4700 |
O2···H10A | 2.5800 | H9···C2vii | 2.94 (3) |
O2···H4v | 2.6800 | H9···C3vii | 3.02 (3) |
O3···H10B | 2.7700 | H10A···O2 | 2.5800 |
O3···H1vi | 1.96 (3) | H10B···O3 | 2.7700 |
O4···H9 | 2.48 (3) | H10B···C1 | 2.9400 |
N1···O1 | 2.693 (3) | H11A···H9 | 2.4700 |
N1···H11B | 2.6900 | H11B···N1 | 2.6900 |
C1···O1 | 3.148 (3) | H11B···C8 | 2.9600 |
C3···O2vi | 3.328 (4) | H11B···O1i | 2.5400 |
C4···O2viii | 3.409 (3) | H12A···O1i | 2.7700 |
C7···S1vii | 3.610 (2) | H12B···S1xi | 3.1100 |
C8···C11 | 3.506 (3) | H12B···H6xii | 2.5100 |
C11—S1—C12 | 100.68 (15) | O1—C13—O2 | 125.0 (2) |
C13—O1—H1 | 108 (2) | C2—C3—H3 | 122.00 |
C1—N1—C8 | 111.95 (17) | C4—C3—H3 | 122.00 |
C1—N1—C9 | 124.23 (18) | C3—C4—H4 | 119.00 |
C8—N1—C9 | 123.80 (18) | C5—C4—H4 | 120.00 |
O3—C1—N1 | 123.8 (2) | C4—C5—H5 | 119.00 |
O3—C1—C2 | 129.8 (2) | C6—C5—H5 | 119.00 |
N1—C1—C2 | 106.38 (18) | C5—C6—H6 | 121.00 |
C1—C2—C7 | 107.94 (18) | C7—C6—H6 | 121.00 |
C3—C2—C7 | 121.8 (2) | N1—C9—H9 | 106.0 (15) |
C1—C2—C3 | 130.2 (2) | C10—C9—H9 | 108.4 (16) |
C2—C3—C4 | 117.0 (3) | C13—C9—H9 | 105.8 (17) |
C3—C4—C5 | 121.0 (3) | C9—C10—H10A | 109.00 |
C4—C5—C6 | 122.0 (3) | C9—C10—H10B | 109.00 |
C5—C6—C7 | 117.1 (3) | C11—C10—H10A | 109.00 |
C2—C7—C8 | 108.42 (19) | C11—C10—H10B | 109.00 |
C6—C7—C8 | 130.4 (2) | H10A—C10—H10B | 108.00 |
C2—C7—C6 | 121.2 (2) | S1—C11—H11A | 110.00 |
O4—C8—N1 | 124.6 (2) | S1—C11—H11B | 110.00 |
N1—C8—C7 | 105.28 (18) | C10—C11—H11A | 110.00 |
O4—C8—C7 | 130.1 (2) | C10—C11—H11B | 110.00 |
N1—C9—C10 | 112.62 (16) | H11A—C11—H11B | 108.00 |
C10—C9—C13 | 112.59 (17) | S1—C12—H12A | 109.00 |
N1—C9—C13 | 110.92 (17) | S1—C12—H12B | 109.00 |
C9—C10—C11 | 111.50 (18) | S1—C12—H12C | 109.00 |
S1—C11—C10 | 109.93 (17) | H12A—C12—H12B | 110.00 |
O1—C13—C9 | 111.22 (18) | H12A—C12—H12C | 109.00 |
O2—C13—C9 | 123.7 (2) | H12B—C12—H12C | 109.00 |
C12—S1—C11—C10 | −178.69 (19) | C1—C2—C7—C8 | −1.1 (2) |
C8—N1—C1—O3 | −178.4 (2) | C3—C2—C7—C6 | 0.0 (4) |
C8—N1—C1—C2 | 1.0 (2) | C3—C2—C7—C8 | 178.1 (2) |
C9—N1—C1—O3 | 2.7 (3) | C2—C3—C4—C5 | 1.0 (4) |
C9—N1—C1—C2 | −177.97 (18) | C3—C4—C5—C6 | −1.0 (5) |
C1—N1—C8—O4 | 177.4 (2) | C4—C5—C6—C7 | 0.5 (5) |
C1—N1—C8—C7 | −1.6 (2) | C5—C6—C7—C2 | 0.0 (4) |
C9—N1—C8—O4 | −3.6 (3) | C5—C6—C7—C8 | −177.6 (3) |
C9—N1—C8—C7 | 177.32 (18) | C2—C7—C8—O4 | −177.3 (2) |
C1—N1—C9—C10 | 72.2 (2) | C2—C7—C8—N1 | 1.7 (2) |
C1—N1—C9—C13 | −55.0 (2) | C6—C7—C8—O4 | 0.6 (4) |
C8—N1—C9—C10 | −106.6 (2) | C6—C7—C8—N1 | 179.6 (3) |
C8—N1—C9—C13 | 126.1 (2) | N1—C9—C10—C11 | 63.5 (2) |
O3—C1—C2—C3 | 0.3 (4) | C13—C9—C10—C11 | −170.15 (18) |
O3—C1—C2—C7 | 179.4 (2) | N1—C9—C13—O1 | −42.6 (2) |
N1—C1—C2—C3 | −179.0 (2) | N1—C9—C13—O2 | 140.5 (2) |
N1—C1—C2—C7 | 0.2 (2) | C10—C9—C13—O1 | −169.85 (18) |
C1—C2—C3—C4 | 178.6 (2) | C10—C9—C13—O2 | 13.3 (3) |
C7—C2—C3—C4 | −0.5 (4) | C9—C10—C11—S1 | −179.19 (15) |
C1—C2—C7—C6 | −179.3 (2) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x−1/2, −y+1, z+1/2; (iii) x+1/2, −y+3/2, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) −x+1/2, −y+1, z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2; (viii) −x+1/2, −y+1, z−1/2; (ix) −x−1/2, −y+1, z−1/2; (x) −x−1, y−1/2, −z+1/2; (xi) x−1/2, −y+3/2, −z+1; (xii) −x−1, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3iv | 0.77 (3) | 1.96 (3) | 2.673 (3) | 154 (3) |
C3—H3···O2vi | 0.9300 | 2.4200 | 3.328 (4) | 165.00 |
C9—H9···O4 | 0.96 (3) | 2.48 (3) | 2.905 (3) | 106.4 (18) |
C11—H11B···O1i | 0.9700 | 2.5400 | 3.443 (3) | 156.00 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (vi) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H13NO4S |
Mr | 279.30 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 6.7923 (6), 9.9581 (8), 20.0970 (17) |
V (Å3) | 1359.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.20 × 0.14 × 0.10 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.969, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7865, 1864, 1679 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.659 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.098, 1.06 |
No. of reflections | 1864 |
No. of parameters | 179 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.33 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.77 (3) | 1.96 (3) | 2.673 (3) | 154 (3) |
C3—H3···O2ii | 0.9300 | 2.4200 | 3.328 (4) | 165.00 |
C9—H9···O4 | 0.96 (3) | 2.48 (3) | 2.905 (3) | 106.4 (18) |
C11—H11B···O1iii | 0.9700 | 2.5400 | 3.443 (3) | 156.00 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2. |
Acknowledgements
The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore, and for technical support, respectively.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Isocoumarin and 3,4-dihydroisocoumarin have shown an impressive array of biological activities such as anti-tumor (Hill et al., 1986), anti-leucemic (Canedo et al., 1997) and anti-microbial (Whyte et al., 1996). The titled compound (I, Fig. 1) is an intermediate towards the synthesis of chiral isocoumarin. The biological activity of the title compound and synthesis of its complexes are in progress.
The crystal structures of 2-Phthalimidoethanoic acid monohydrate (Feeder & Jones, 1994), N-Phthaloylglycine (Barooah et al., 2007) and DL-Methioninium trichloroacetate (Rajagopal et al., 2003) have been published which contain the moieties of the title compound.
In the title compound the aromatic ring and heterocyclic ring along with O-atoms of carbonyl groups A (C1—C8/N1/O3/O4), the linear chain B (C9—C11/S1/C12) and the carboxylate group C (O1/C13/O2) are planar. There exists an intramolecular H-bond of type C—H···O completing a planar S(5) ring motif (Bernstein et al., 1995). The value of dihedral angle between A/B, A/C and B/C is 80.04 (7)°, 79.14 (18)° and 20.54 (30)°, respectively. Due to the intermolecular H-bonding (Table 1), the molecules are connected in one dimensional polymeric chains through ring motifs R22(9) extending along the b-axis.