Literature DB >> 21583673

(2R)-2-(1,3-Dioxoisoindolin-2-yl)-4-(methyl-sulfan-yl)butanoic acid.

Abdul Rauf Raza, M Nawaz Tahir, Aisha Saddiqa, Muhammad Danish, M Saeed Iqbal.   

Abstract

The title compound, C(13)H(13)NO(4)S, 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 carboxyl-ate group. An intra-molecular 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, mol-ecules are connected through O-H⋯O and C-H⋯O hydrogen bonds with R(2) (2)(9) ring motifs into chains extending along the b axis.

Entities:  

Year:  2009        PMID： 21583673      PMCID： PMC2977145          DOI： 10.1107/S1600536809028992

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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

C13H13NO4S M = 279.30 Orthorhombic, a = 6.7923 (6) Å b = 9.9581 (8) Å c = 20.0970 (17) Å V = 1359.3 (2) Å3 Z = 4 Mo Kα radiation μ = 0.25 mm−1 T = 296 K 0.20 × 0.14 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.969, T max = 0.985 7865 measured reflections 1864 independent reflections 1679 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.098 S = 1.06 1864 reflections 179 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.20 e Å−3 Δρmin = −0.33 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/S1600536809028992/pb2001sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028992/pb2001Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H13NO4SF(000) = 584
Mr = 279.30Dx = 1.365 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1864 reflections
a = 6.7923 (6) Åθ = 2.3–28.0°
b = 9.9581 (8) ŵ = 0.25 mm−1
c = 20.0970 (17) ÅT = 296 K
V = 1359.3 (2) Å3Prismatic, colorless
Z = 40.20 × 0.14 × 0.10 mm
Bruker Kappa APEXII CCD diffractometer1864 independent reflections
Radiation source: fine-focus sealed tube1679 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 7.50 pixels mm-1θmax = 28.0°, θmin = 2.3°
ω scansh = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −12→7
Tmin = 0.969, Tmax = 0.985l = −23→26
7865 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.057P)2 + 0.2154P] where P = (Fo2 + 2Fc2)/3
1864 reflections(Δ/σ)max < 0.001
179 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.33 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 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.
xyzUiso*/Ueq
S1−0.16661 (11)0.67441 (7)0.42200 (3)0.0592 (2)
O10.3364 (3)0.2322 (2)0.26744 (9)0.0561 (6)
O20.3978 (3)0.3163 (2)0.36803 (8)0.0651 (7)
O30.3730 (2)0.55141 (18)0.23747 (8)0.0475 (5)
O4−0.2132 (3)0.3346 (2)0.21563 (10)0.0656 (7)
N10.0832 (3)0.43417 (17)0.24261 (8)0.0355 (5)
C10.2192 (3)0.5168 (2)0.21199 (11)0.0361 (6)
C20.1381 (4)0.5487 (2)0.14518 (10)0.0390 (6)
C30.2158 (5)0.6255 (3)0.09427 (12)0.0543 (8)
C40.1055 (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)
C90.1029 (3)0.3829 (2)0.31004 (10)0.0358 (6)
C100.0710 (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)
C130.2982 (3)0.3089 (2)0.31883 (11)0.0412 (6)
H10.435 (5)0.196 (3)0.2742 (16)0.0673*
H30.336220.669100.098730.0652*
H40.153900.684380.000300.0764*
H5−0.144590.58059−0.009040.0801*
H6−0.272200.451410.077120.0713*
H90.002 (4)0.316 (3)0.3151 (12)0.0430*
H10A0.095950.453600.406360.0507*
H10B0.163740.563730.355430.0507*
H11A−0.230380.474360.368340.0558*
H11B−0.163210.583250.316510.0558*
H12A−0.437040.752260.365760.1385*
H12B−0.457050.784520.441810.1385*
H12C−0.499500.639050.415680.1385*
U11U22U33U12U13U23
S10.0668 (4)0.0560 (3)0.0549 (4)0.0046 (3)0.0121 (3)−0.0137 (3)
O10.0542 (10)0.0646 (11)0.0494 (10)0.0238 (9)−0.0114 (9)−0.0182 (9)
O20.0685 (11)0.0852 (14)0.0417 (9)0.0298 (11)−0.0157 (8)−0.0100 (9)
O30.0448 (8)0.0545 (9)0.0432 (9)−0.0130 (8)−0.0076 (7)0.0070 (7)
O40.0510 (10)0.0801 (13)0.0656 (12)−0.0252 (10)−0.0100 (9)0.0065 (11)
N10.0360 (8)0.0381 (8)0.0323 (8)−0.0015 (8)−0.0004 (7)0.0012 (7)
C10.0399 (10)0.0326 (9)0.0359 (10)0.0005 (8)0.0000 (8)−0.0018 (8)
C20.0508 (12)0.0346 (9)0.0315 (10)0.0027 (9)−0.0023 (9)−0.0029 (8)
C30.0728 (17)0.0508 (12)0.0394 (12)−0.0090 (12)−0.0011 (12)0.0059 (10)
C40.097 (2)0.0591 (14)0.0353 (12)−0.0061 (16)−0.0088 (14)0.0057 (11)
C50.100 (2)0.0601 (15)0.0404 (13)0.0027 (17)−0.0261 (15)0.0002 (12)
C60.0686 (16)0.0573 (13)0.0524 (14)−0.0024 (14)−0.0235 (14)−0.0051 (12)
C70.0502 (12)0.0398 (10)0.0391 (11)0.0021 (10)−0.0066 (10)−0.0046 (9)
C80.0398 (11)0.0440 (11)0.0427 (12)−0.0016 (9)−0.0058 (9)−0.0035 (9)
C90.0382 (10)0.0369 (10)0.0324 (10)0.0002 (9)0.0022 (8)0.0020 (8)
C100.0460 (12)0.0467 (11)0.0342 (10)0.0049 (10)0.0008 (9)−0.0039 (9)
C110.0494 (12)0.0517 (12)0.0383 (11)0.0096 (11)0.0036 (10)−0.0045 (10)
C120.089 (2)0.111 (3)0.078 (2)0.053 (2)0.0201 (19)−0.001 (2)
C130.0466 (11)0.0424 (10)0.0347 (10)0.0074 (10)0.0002 (9)0.0013 (9)
S1—C111.792 (3)C7—C81.488 (3)
S1—C121.786 (4)C9—C131.528 (3)
O1—C131.311 (3)C9—C101.525 (3)
O2—C131.200 (3)C10—C111.516 (3)
O3—C11.213 (3)C3—H30.9300
O4—C81.199 (3)C4—H40.9300
O1—H10.77 (3)C5—H50.9300
N1—C81.407 (3)C6—H60.9300
N1—C91.454 (3)C9—H90.96 (3)
N1—C11.382 (3)C10—H10A0.9700
C1—C21.486 (3)C10—H10B0.9700
C2—C71.383 (4)C11—H11A0.9700
C2—C31.382 (3)C11—H11B0.9700
C3—C41.395 (4)C12—H12A0.9600
C4—C51.374 (5)C12—H12B0.9600
C5—C61.389 (4)C12—H12C0.9600
C6—C71.382 (4)
S1···C7i3.610 (2)C10···O33.301 (3)
S1···H5ii3.1600C11···C83.506 (3)
S1···H12Biii3.1100C13···O32.960 (3)
O1···N12.693 (3)C1···H1vi2.96 (3)
O1···C13.148 (3)C1···H10B2.9400
O1···O3iv2.673 (3)C2···H9i2.94 (3)
O2···C4v3.409 (3)C3···H9i3.02 (3)
O2···C3iv3.328 (4)C8···H11B2.9600
O3···C132.960 (3)H1···O3iv1.96 (3)
O3···C103.301 (3)H1···C1iv2.96 (3)
O3···O4i3.165 (3)H3···O2vi2.4200
O3···O1vi2.673 (3)H4···O2viii2.6800
O4···O3vii3.165 (3)H5···S1ix3.1600
O1···H12Avii2.7700H6···H12Bx2.5100
O1···H11Bvii2.5400H9···O42.48 (3)
O2···H3iv2.4200H9···H11A2.4700
O2···H10A2.5800H9···C2vii2.94 (3)
O2···H4v2.6800H9···C3vii3.02 (3)
O3···H10B2.7700H10A···O22.5800
O3···H1vi1.96 (3)H10B···O32.7700
O4···H92.48 (3)H10B···C12.9400
N1···O12.693 (3)H11A···H92.4700
N1···H11B2.6900H11B···N12.6900
C1···O13.148 (3)H11B···C82.9600
C3···O2vi3.328 (4)H11B···O1i2.5400
C4···O2viii3.409 (3)H12A···O1i2.7700
C7···S1vii3.610 (2)H12B···S1xi3.1100
C8···C113.506 (3)H12B···H6xii2.5100
C11—S1—C12100.68 (15)O1—C13—O2125.0 (2)
C13—O1—H1108 (2)C2—C3—H3122.00
C1—N1—C8111.95 (17)C4—C3—H3122.00
C1—N1—C9124.23 (18)C3—C4—H4119.00
C8—N1—C9123.80 (18)C5—C4—H4120.00
O3—C1—N1123.8 (2)C4—C5—H5119.00
O3—C1—C2129.8 (2)C6—C5—H5119.00
N1—C1—C2106.38 (18)C5—C6—H6121.00
C1—C2—C7107.94 (18)C7—C6—H6121.00
C3—C2—C7121.8 (2)N1—C9—H9106.0 (15)
C1—C2—C3130.2 (2)C10—C9—H9108.4 (16)
C2—C3—C4117.0 (3)C13—C9—H9105.8 (17)
C3—C4—C5121.0 (3)C9—C10—H10A109.00
C4—C5—C6122.0 (3)C9—C10—H10B109.00
C5—C6—C7117.1 (3)C11—C10—H10A109.00
C2—C7—C8108.42 (19)C11—C10—H10B109.00
C6—C7—C8130.4 (2)H10A—C10—H10B108.00
C2—C7—C6121.2 (2)S1—C11—H11A110.00
O4—C8—N1124.6 (2)S1—C11—H11B110.00
N1—C8—C7105.28 (18)C10—C11—H11A110.00
O4—C8—C7130.1 (2)C10—C11—H11B110.00
N1—C9—C10112.62 (16)H11A—C11—H11B108.00
C10—C9—C13112.59 (17)S1—C12—H12A109.00
N1—C9—C13110.92 (17)S1—C12—H12B109.00
C9—C10—C11111.50 (18)S1—C12—H12C109.00
S1—C11—C10109.93 (17)H12A—C12—H12B110.00
O1—C13—C9111.22 (18)H12A—C12—H12C109.00
O2—C13—C9123.7 (2)H12B—C12—H12C109.00
C12—S1—C11—C10−178.69 (19)C1—C2—C7—C8−1.1 (2)
C8—N1—C1—O3−178.4 (2)C3—C2—C7—C60.0 (4)
C8—N1—C1—C21.0 (2)C3—C2—C7—C8178.1 (2)
C9—N1—C1—O32.7 (3)C2—C3—C4—C51.0 (4)
C9—N1—C1—C2−177.97 (18)C3—C4—C5—C6−1.0 (5)
C1—N1—C8—O4177.4 (2)C4—C5—C6—C70.5 (5)
C1—N1—C8—C7−1.6 (2)C5—C6—C7—C20.0 (4)
C9—N1—C8—O4−3.6 (3)C5—C6—C7—C8−177.6 (3)
C9—N1—C8—C7177.32 (18)C2—C7—C8—O4−177.3 (2)
C1—N1—C9—C1072.2 (2)C2—C7—C8—N11.7 (2)
C1—N1—C9—C13−55.0 (2)C6—C7—C8—O40.6 (4)
C8—N1—C9—C10−106.6 (2)C6—C7—C8—N1179.6 (3)
C8—N1—C9—C13126.1 (2)N1—C9—C10—C1163.5 (2)
O3—C1—C2—C30.3 (4)C13—C9—C10—C11−170.15 (18)
O3—C1—C2—C7179.4 (2)N1—C9—C13—O1−42.6 (2)
N1—C1—C2—C3−179.0 (2)N1—C9—C13—O2140.5 (2)
N1—C1—C2—C70.2 (2)C10—C9—C13—O1−169.85 (18)
C1—C2—C3—C4178.6 (2)C10—C9—C13—O213.3 (3)
C7—C2—C3—C4−0.5 (4)C9—C10—C11—S1−179.19 (15)
C1—C2—C7—C6−179.3 (2)
D—H···AD—HH···AD···AD—H···A
O1—H1···O3iv0.77 (3)1.96 (3)2.673 (3)154 (3)
C3—H3···O2vi0.93002.42003.328 (4)165.00
C9—H9···O40.96 (3)2.48 (3)2.905 (3)106.4 (18)
C11—H11B···O1i0.97002.54003.443 (3)156.00
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯O3i0.77 (3)1.96 (3)2.673 (3)154 (3)
C3—H3⋯O2ii0.93002.42003.328 (4)165.00
C9—H9⋯O40.96 (3)2.48 (3)2.905 (3)106.4 (18)
C11—H11B⋯O1iii0.97002.54003.443 (3)156.00

Symmetry codes: (i) ; (ii) ; (iii) .

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

Authors:  Abdul Rauf Raza; Aisha Saddiqa; M Nawaz Tahir; Muhammad Danish; Talat Majeed
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-10

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

Authors:  Abdul Rauf Raza; Aisha Saddiqa; M Nawaz Tahir; Sadia Saddiq
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