organic compounds
(E)-Methyl 3-(3,4-dimethoxyphenyl)-2-[(1,3-dioxoisoindolin-2-yl)methyl]acrylate
aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, bDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India, and cDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
*Correspondence e-mail: smurugavel27@gmail.com
In the title compound, C21H19NO6, the isoindole ring system is essentially planar [maximum deviation = 0.019 (2) Å for the N atom] and is oriented at a dihedral angle of 51.3 (1)° with respect to the benzene ring. The two methoxy groups are almost coplanar with the attached benzene ring [C—O—C—C = 3.7 (4) and 4.3 (4)°]. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(9) ring motif. In the crystal, molecules are linked through bifurcated C—H⋯(O,O) hydrogen bonds having R12(5) ring motifs, forming chains along the b-axis direction. The crystal packing is further stabilzed by π–π interactions [centriod–centroid distance = 3.463 (1) Å].
Related literature
For background to the applications of isoindolins, see: Pendrak et al. (1994); De Clerck (1995); Stowers (1996); Heaney & Shuhaibar (1995). For related structures, see: Liu et al. (2004); Liang & Li (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812010975/bt5842sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812010975/bt5842Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812010975/bt5842Isup3.cml
A solution of 2,3-dihydro-1H-isoindole-1,3-dione (1 mmol, 0.147 g) and potassiumcarbonate (1.5 mmol, 0.207 g) in acetonitrile as solvent was stirred for 15 minutes at room temperature. To this solution, methyl (2Z)-2-(bromomethyl)-3-(3,4-dimethoxyphenyl)prop-2-enoate (1 mmol, 0.315 g) was added till the addition is complete. After the completion of the reaction as indicated by TLC, acetonitrile solvent was evaporated. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through pad of silica gel (100–200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colorless solid (0.375 g, 98% yield). Recrystallization was carried out using ethylacetate as solvent.
H atoms were positioned geometrically, with C—H = 0.93–0.98 Å and constrained to ride on their parent atom, with Uiso(H)=1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.
Isoindolinones and their derivatives have been investigated widely due to their physiological and chemotherapeutic properties. Many compounds containing the isoindolinone skeleton have shown antiviral, antileukemic, antiinflammatory, antipsychotic and antiulcer properties (Pendrak et al., 1994; De Clerck, 1995). Isoindolinones are useful for the synthesis of various drugs and naturally occurring compounds (Stowers, 1996; Heaney & Shuhaibar, 1995). In view of this biological importance, the
of the title compound has been determined and the results are presented here.Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The isoindole ring system is essentially planar [maximum deviation = 0.019 (2) Å for the N1 atom] and is oriented at a dihedral angle of 51.3 (1)° with respect to the benzene ring. The methyl acrylate (O3/O4/C10–C14) plane forms dihedral angles of 83.2 (1)° and 43.7 (1)°, respectively, with the isoindole and benzene rings. The two methoxy groups at C18 and C17 are almost coplanar with the attached benzene ring as evidenced by torsion angles of C21–O6–C18–C19 = 3.7 (4) and C20–O5–C17–C16 = 4.3 (4)°, respectively. The sum of bond angles around N1 (359.9°) indicates that N1 is in sp2
The keto atoms O1 and O2 deviate by 0.034 (2) and -0.004 (2) Å, respectively, from the isoindole ring. The geometric parameters of the title molecule agrees well with those reported for similar structures (Liu et al., 2004, Liang & Li 2006).The molecular structure is stabilized by C15—H15···O1 intramolecular hydrogen bond, forming S(9) ring motif (Bernstein et al., 1995) (Table 1). In the crystal, the molecules are linked by intermolecular C4—H4···O5i and C4—H4···O6i hydrogen bonds (Table 1; Symmetry code: (i) = 1 + x, y, z)) generating a bifurcated R12(5) ring motif, resulting in an extended one dimensional chains along the b axis (Fig. 2). The crystal packing is further stabilized by π—π interactions with centroid—centroid distances: Cg1—Cg2iii = 3.463 (1) Å and Cg2—Cg1iv = 3.463 (1) Å (Fig. 3; Cg1 and Cg2 are the centroids of N1/C1/C2/C7/C8 indole ring and C14–C19 benzene ring, respectively, symmetry code as in Fig. 3).
For background to the applications of isoindolins, see: Pendrak et al. (1994); De Clerck (1995); Stowers (1996); Heaney & Shuhaibar (1995). For related structures, see: Liu et al. (2004); Liang & Li (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C21H19NO6 | F(000) = 800 |
Mr = 381.37 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5078 reflections |
a = 15.0613 (8) Å | θ = 2.7–29.0° |
b = 7.6334 (4) Å | µ = 0.10 mm−1 |
c = 16.6354 (8) Å | T = 293 K |
β = 93.522 (2)° | Block, colourless |
V = 1908.94 (17) Å3 | 0.25 × 0.23 × 0.17 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 5063 independent reflections |
Radiation source: fine-focus sealed tube | 3241 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 10.0 pixels mm-1 | θmax = 29.0°, θmin = 2.7° |
ω scans | h = −20→20 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→9 |
Tmin = 0.976, Tmax = 0.983 | l = −14→22 |
21209 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.197 | w = 1/[σ2(Fo2) + (0.0874P)2 + 0.8631P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5063 reflections | Δρmax = 0.26 e Å−3 |
257 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.010 (2) |
C21H19NO6 | V = 1908.94 (17) Å3 |
Mr = 381.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.0613 (8) Å | µ = 0.10 mm−1 |
b = 7.6334 (4) Å | T = 293 K |
c = 16.6354 (8) Å | 0.25 × 0.23 × 0.17 mm |
β = 93.522 (2)° |
Bruker APEXII CCD diffractometer | 5063 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3241 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.983 | Rint = 0.036 |
21209 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.26 e Å−3 |
5063 reflections | Δρmin = −0.17 e Å−3 |
257 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
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 | ||
N1 | 0.14320 (11) | 0.1401 (2) | 0.33185 (10) | 0.0424 (4) | |
O1 | 0.09640 (11) | 0.0065 (3) | 0.21318 (10) | 0.0573 (5) | |
O3 | 0.16679 (10) | −0.1006 (2) | 0.45930 (10) | 0.0548 (4) | |
C14 | −0.13047 (13) | −0.0184 (3) | 0.32900 (12) | 0.0406 (5) | |
O5 | −0.35924 (10) | 0.1490 (3) | 0.20022 (11) | 0.0632 (5) | |
O2 | 0.23094 (13) | 0.2752 (3) | 0.43312 (11) | 0.0670 (5) | |
O6 | −0.37165 (11) | 0.0404 (3) | 0.34609 (11) | 0.0733 (6) | |
C11 | 0.09073 (13) | −0.1416 (3) | 0.44408 (11) | 0.0393 (5) | |
C13 | −0.05573 (13) | −0.0948 (3) | 0.37754 (12) | 0.0424 (5) | |
H13 | −0.0679 | −0.2017 | 0.4013 | 0.051* | |
O4 | 0.05602 (11) | −0.2889 (2) | 0.47147 (10) | 0.0562 (4) | |
C16 | −0.19917 (14) | 0.1059 (3) | 0.20806 (13) | 0.0464 (5) | |
H16 | −0.1940 | 0.1488 | 0.1562 | 0.056* | |
C15 | −0.12410 (13) | 0.0491 (3) | 0.25270 (13) | 0.0445 (5) | |
H15 | −0.0688 | 0.0566 | 0.2310 | 0.053* | |
C10 | 0.02695 (13) | −0.0361 (3) | 0.39320 (11) | 0.0382 (4) | |
C8 | 0.15518 (13) | 0.0666 (3) | 0.25730 (13) | 0.0434 (5) | |
C17 | −0.28144 (13) | 0.0993 (3) | 0.23975 (14) | 0.0456 (5) | |
C9 | 0.05918 (13) | 0.1426 (3) | 0.37010 (13) | 0.0415 (5) | |
H9A | 0.0145 | 0.1966 | 0.3337 | 0.050* | |
H9B | 0.0656 | 0.2148 | 0.4181 | 0.050* | |
C19 | −0.21432 (14) | −0.0266 (3) | 0.36066 (13) | 0.0460 (5) | |
H19 | −0.2199 | −0.0754 | 0.4113 | 0.055* | |
C18 | −0.28843 (13) | 0.0364 (3) | 0.31812 (13) | 0.0472 (5) | |
C1 | 0.22284 (15) | 0.2025 (3) | 0.36886 (15) | 0.0493 (5) | |
C7 | 0.25214 (15) | 0.0779 (3) | 0.24589 (15) | 0.0515 (6) | |
C2 | 0.29162 (14) | 0.1602 (3) | 0.31177 (16) | 0.0538 (6) | |
C12 | 0.11416 (19) | −0.3925 (4) | 0.52426 (17) | 0.0632 (7) | |
H12A | 0.1582 | −0.4481 | 0.4936 | 0.095* | |
H12B | 0.0801 | −0.4803 | 0.5499 | 0.095* | |
H12C | 0.1430 | −0.3183 | 0.5645 | 0.095* | |
C20 | −0.35659 (18) | 0.2005 (5) | 0.11918 (18) | 0.0733 (8) | |
H20A | −0.3193 | 0.3019 | 0.1157 | 0.110* | |
H20B | −0.4156 | 0.2281 | 0.0980 | 0.110* | |
H20C | −0.3330 | 0.1066 | 0.0885 | 0.110* | |
C3 | 0.38247 (17) | 0.1899 (4) | 0.3186 (2) | 0.0751 (9) | |
H3 | 0.4095 | 0.2460 | 0.3633 | 0.090* | |
C6 | 0.29985 (19) | 0.0199 (4) | 0.1836 (2) | 0.0729 (8) | |
H6 | 0.2727 | −0.0361 | 0.1390 | 0.087* | |
C21 | −0.3808 (2) | −0.0149 (7) | 0.42584 (19) | 0.1007 (14) | |
H21A | −0.3607 | −0.1338 | 0.4318 | 0.151* | |
H21B | −0.4421 | −0.0078 | 0.4380 | 0.151* | |
H21C | −0.3457 | 0.0591 | 0.4620 | 0.151* | |
C4 | 0.43088 (19) | 0.1328 (6) | 0.2565 (3) | 0.0924 (11) | |
H4 | 0.4920 | 0.1512 | 0.2589 | 0.111* | |
C5 | 0.3909 (2) | 0.0494 (6) | 0.1909 (3) | 0.0950 (12) | |
H5 | 0.4258 | 0.0114 | 0.1501 | 0.114* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0315 (8) | 0.0505 (10) | 0.0451 (9) | −0.0048 (7) | 0.0017 (7) | 0.0023 (8) |
O1 | 0.0408 (8) | 0.0798 (12) | 0.0511 (9) | −0.0029 (8) | 0.0002 (7) | −0.0105 (8) |
O3 | 0.0353 (8) | 0.0664 (11) | 0.0615 (10) | −0.0024 (7) | −0.0063 (7) | 0.0094 (8) |
C14 | 0.0318 (9) | 0.0448 (11) | 0.0450 (11) | −0.0035 (8) | −0.0001 (8) | −0.0056 (9) |
O5 | 0.0325 (8) | 0.0895 (14) | 0.0664 (11) | 0.0066 (8) | −0.0053 (7) | 0.0092 (10) |
O2 | 0.0611 (11) | 0.0705 (12) | 0.0675 (11) | −0.0154 (9) | −0.0101 (9) | −0.0092 (10) |
O6 | 0.0311 (8) | 0.1258 (18) | 0.0637 (11) | 0.0017 (10) | 0.0091 (7) | 0.0027 (11) |
C11 | 0.0340 (10) | 0.0487 (12) | 0.0357 (9) | 0.0010 (8) | 0.0059 (7) | −0.0045 (9) |
C13 | 0.0365 (10) | 0.0470 (12) | 0.0437 (10) | −0.0024 (9) | 0.0024 (8) | 0.0000 (9) |
O4 | 0.0451 (9) | 0.0584 (10) | 0.0644 (10) | −0.0024 (7) | −0.0021 (7) | 0.0178 (8) |
C16 | 0.0379 (11) | 0.0550 (13) | 0.0463 (11) | −0.0013 (9) | 0.0018 (9) | 0.0039 (10) |
C15 | 0.0304 (9) | 0.0537 (13) | 0.0496 (11) | −0.0020 (9) | 0.0038 (8) | −0.0007 (10) |
C10 | 0.0329 (9) | 0.0450 (11) | 0.0370 (9) | 0.0023 (8) | 0.0043 (7) | −0.0043 (8) |
C8 | 0.0333 (10) | 0.0498 (12) | 0.0473 (11) | 0.0004 (9) | 0.0036 (8) | 0.0078 (9) |
C17 | 0.0287 (10) | 0.0536 (13) | 0.0537 (12) | −0.0002 (9) | −0.0031 (8) | −0.0044 (10) |
C9 | 0.0317 (10) | 0.0455 (12) | 0.0474 (11) | 0.0005 (8) | 0.0034 (8) | −0.0016 (9) |
C19 | 0.0349 (10) | 0.0601 (14) | 0.0428 (11) | −0.0061 (9) | 0.0017 (8) | −0.0036 (10) |
C18 | 0.0281 (9) | 0.0636 (14) | 0.0503 (12) | −0.0037 (9) | 0.0049 (8) | −0.0070 (10) |
C1 | 0.0387 (11) | 0.0500 (13) | 0.0580 (13) | −0.0077 (9) | −0.0063 (9) | 0.0083 (11) |
C7 | 0.0374 (11) | 0.0564 (14) | 0.0613 (13) | 0.0008 (10) | 0.0086 (10) | 0.0134 (11) |
C2 | 0.0319 (11) | 0.0551 (14) | 0.0739 (16) | −0.0022 (10) | −0.0009 (10) | 0.0179 (12) |
C12 | 0.0630 (16) | 0.0607 (16) | 0.0651 (15) | 0.0061 (12) | −0.0027 (12) | 0.0180 (13) |
C20 | 0.0498 (15) | 0.096 (2) | 0.0717 (17) | 0.0044 (14) | −0.0136 (12) | 0.0157 (16) |
C3 | 0.0358 (13) | 0.083 (2) | 0.105 (2) | −0.0079 (13) | −0.0043 (14) | 0.0220 (17) |
C6 | 0.0498 (15) | 0.091 (2) | 0.0801 (18) | 0.0045 (14) | 0.0206 (13) | 0.0042 (16) |
C21 | 0.0527 (17) | 0.184 (4) | 0.0680 (18) | −0.005 (2) | 0.0229 (14) | 0.006 (2) |
C4 | 0.0316 (13) | 0.115 (3) | 0.131 (3) | 0.0001 (15) | 0.0126 (16) | 0.025 (2) |
C5 | 0.0522 (17) | 0.117 (3) | 0.119 (3) | 0.0103 (19) | 0.0360 (19) | 0.013 (2) |
N1—C8 | 1.383 (3) | C9—H9A | 0.9700 |
N1—C1 | 1.398 (3) | C9—H9B | 0.9700 |
N1—C9 | 1.451 (3) | C19—C18 | 1.371 (3) |
O1—C8 | 1.205 (3) | C19—H19 | 0.9300 |
O3—C11 | 1.200 (2) | C1—C2 | 1.483 (4) |
C14—C15 | 1.379 (3) | C7—C2 | 1.367 (4) |
C14—C19 | 1.399 (3) | C7—C6 | 1.370 (4) |
C14—C13 | 1.465 (3) | C2—C3 | 1.385 (3) |
O5—C17 | 1.362 (3) | C12—H12A | 0.9600 |
O5—C20 | 1.407 (3) | C12—H12B | 0.9600 |
O2—C1 | 1.204 (3) | C12—H12C | 0.9600 |
O6—C18 | 1.364 (3) | C20—H20A | 0.9600 |
O6—C21 | 1.407 (4) | C20—H20B | 0.9600 |
C11—O4 | 1.332 (3) | C20—H20C | 0.9600 |
C11—C10 | 1.479 (3) | C3—C4 | 1.372 (5) |
C13—C10 | 1.334 (3) | C3—H3 | 0.9300 |
C13—H13 | 0.9300 | C6—C5 | 1.388 (4) |
O4—C12 | 1.438 (3) | C6—H6 | 0.9300 |
C16—C17 | 1.377 (3) | C21—H21A | 0.9600 |
C16—C15 | 1.383 (3) | C21—H21B | 0.9600 |
C16—H16 | 0.9300 | C21—H21C | 0.9600 |
C15—H15 | 0.9300 | C4—C5 | 1.370 (6) |
C10—C9 | 1.505 (3) | C4—H4 | 0.9300 |
C8—C7 | 1.487 (3) | C5—H5 | 0.9300 |
C17—C18 | 1.399 (3) | ||
C8—N1—C1 | 112.17 (18) | C19—C18—C17 | 119.71 (19) |
C8—N1—C9 | 124.33 (17) | O2—C1—N1 | 125.8 (2) |
C1—N1—C9 | 123.38 (19) | O2—C1—C2 | 129.2 (2) |
C15—C14—C19 | 118.60 (19) | N1—C1—C2 | 104.9 (2) |
C15—C14—C13 | 124.16 (18) | C2—C7—C6 | 122.1 (2) |
C19—C14—C13 | 117.08 (19) | C2—C7—C8 | 107.8 (2) |
C17—O5—C20 | 117.79 (19) | C6—C7—C8 | 130.0 (3) |
C18—O6—C21 | 117.4 (2) | C7—C2—C3 | 121.3 (3) |
O3—C11—O4 | 122.55 (19) | C7—C2—C1 | 109.08 (19) |
O3—C11—C10 | 123.8 (2) | C3—C2—C1 | 129.6 (3) |
O4—C11—C10 | 113.62 (17) | O4—C12—H12A | 109.5 |
C10—C13—C14 | 130.6 (2) | O4—C12—H12B | 109.5 |
C10—C13—H13 | 114.7 | H12A—C12—H12B | 109.5 |
C14—C13—H13 | 114.7 | O4—C12—H12C | 109.5 |
C11—O4—C12 | 115.85 (19) | H12A—C12—H12C | 109.5 |
C17—C16—C15 | 120.5 (2) | H12B—C12—H12C | 109.5 |
C17—C16—H16 | 119.7 | O5—C20—H20A | 109.5 |
C15—C16—H16 | 119.7 | O5—C20—H20B | 109.5 |
C14—C15—C16 | 120.69 (19) | H20A—C20—H20B | 109.5 |
C14—C15—H15 | 119.7 | O5—C20—H20C | 109.5 |
C16—C15—H15 | 119.7 | H20A—C20—H20C | 109.5 |
C13—C10—C11 | 119.64 (19) | H20B—C20—H20C | 109.5 |
C13—C10—C9 | 124.47 (19) | C4—C3—C2 | 117.0 (3) |
C11—C10—C9 | 115.55 (17) | C4—C3—H3 | 121.5 |
O1—C8—N1 | 124.68 (19) | C2—C3—H3 | 121.5 |
O1—C8—C7 | 129.4 (2) | C7—C6—C5 | 116.3 (3) |
N1—C8—C7 | 105.93 (18) | C7—C6—H6 | 121.8 |
O5—C17—C16 | 124.9 (2) | C5—C6—H6 | 121.8 |
O5—C17—C18 | 115.70 (19) | O6—C21—H21A | 109.5 |
C16—C17—C18 | 119.35 (19) | O6—C21—H21B | 109.5 |
N1—C9—C10 | 113.80 (17) | H21A—C21—H21B | 109.5 |
N1—C9—H9A | 108.8 | O6—C21—H21C | 109.5 |
C10—C9—H9A | 108.8 | H21A—C21—H21C | 109.5 |
N1—C9—H9B | 108.8 | H21B—C21—H21C | 109.5 |
C10—C9—H9B | 108.8 | C5—C4—C3 | 121.3 (3) |
H9A—C9—H9B | 107.7 | C5—C4—H4 | 119.4 |
C18—C19—C14 | 121.0 (2) | C3—C4—H4 | 119.4 |
C18—C19—H19 | 119.5 | C4—C5—C6 | 121.9 (3) |
C14—C19—H19 | 119.5 | C4—C5—H5 | 119.0 |
O6—C18—C19 | 124.6 (2) | C6—C5—H5 | 119.0 |
O6—C18—C17 | 115.68 (19) | ||
C15—C14—C13—C10 | 47.1 (3) | C14—C19—C18—O6 | −176.9 (2) |
C19—C14—C13—C10 | −137.5 (2) | C14—C19—C18—C17 | 4.3 (3) |
O3—C11—O4—C12 | 3.1 (3) | O5—C17—C18—O6 | −2.9 (3) |
C10—C11—O4—C12 | −177.31 (19) | C16—C17—C18—O6 | 177.6 (2) |
C19—C14—C15—C16 | −0.7 (3) | O5—C17—C18—C19 | 176.0 (2) |
C13—C14—C15—C16 | 174.6 (2) | C16—C17—C18—C19 | −3.5 (3) |
C17—C16—C15—C14 | 1.4 (4) | C8—N1—C1—O2 | 178.5 (2) |
C14—C13—C10—C11 | −179.2 (2) | C9—N1—C1—O2 | −5.3 (4) |
C14—C13—C10—C9 | 7.8 (4) | C8—N1—C1—C2 | −1.1 (2) |
O3—C11—C10—C13 | 178.0 (2) | C9—N1—C1—C2 | 175.14 (19) |
O4—C11—C10—C13 | −1.6 (3) | O1—C8—C7—C2 | 178.8 (2) |
O3—C11—C10—C9 | −8.4 (3) | N1—C8—C7—C2 | −1.7 (3) |
O4—C11—C10—C9 | 172.04 (17) | O1—C8—C7—C6 | −1.6 (4) |
C1—N1—C8—O1 | −178.7 (2) | N1—C8—C7—C6 | 177.9 (3) |
C9—N1—C8—O1 | 5.1 (4) | C6—C7—C2—C3 | 0.3 (4) |
C1—N1—C8—C7 | 1.7 (2) | C8—C7—C2—C3 | 180.0 (2) |
C9—N1—C8—C7 | −174.50 (19) | C6—C7—C2—C1 | −178.6 (2) |
C20—O5—C17—C16 | 4.3 (4) | C8—C7—C2—C1 | 1.0 (3) |
C20—O5—C17—C18 | −175.2 (2) | O2—C1—C2—C7 | −179.6 (3) |
C15—C16—C17—O5 | −178.8 (2) | N1—C1—C2—C7 | 0.0 (3) |
C15—C16—C17—C18 | 0.7 (4) | O2—C1—C2—C3 | 1.6 (5) |
C8—N1—C9—C10 | 66.3 (3) | N1—C1—C2—C3 | −178.8 (3) |
C1—N1—C9—C10 | −109.5 (2) | C7—C2—C3—C4 | −0.1 (4) |
C13—C10—C9—N1 | −132.6 (2) | C1—C2—C3—C4 | 178.6 (3) |
C11—C10—C9—N1 | 54.2 (2) | C2—C7—C6—C5 | −0.1 (4) |
C15—C14—C19—C18 | −2.2 (3) | C8—C7—C6—C5 | −179.6 (3) |
C13—C14—C19—C18 | −177.8 (2) | C2—C3—C4—C5 | −0.4 (5) |
C21—O6—C18—C19 | 3.7 (4) | C3—C4—C5—C6 | 0.7 (6) |
C21—O6—C18—C17 | −177.4 (3) | C7—C6—C5—C4 | −0.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1 | 0.93 | 2.55 | 3.440 (3) | 160 |
C4—H4···O5i | 0.93 | 2.50 | 3.354 (3) | 153 |
C4—H4···O6i | 0.93 | 2.58 | 3.320 (4) | 137 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C21H19NO6 |
Mr | 381.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 15.0613 (8), 7.6334 (4), 16.6354 (8) |
β (°) | 93.522 (2) |
V (Å3) | 1908.94 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.25 × 0.23 × 0.17 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.976, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21209, 5063, 3241 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.682 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.197, 1.06 |
No. of reflections | 5063 |
No. of parameters | 257 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.17 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1 | 0.93 | 2.55 | 3.440 (3) | 160 |
C4—H4···O5i | 0.93 | 2.50 | 3.354 (3) | 153.1 |
C4—H4···O6i | 0.93 | 2.58 | 3.320 (4) | 136.5 |
Symmetry code: (i) x+1, y, z. |
Footnotes
‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.
Acknowledgements
The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.
References
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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.
Isoindolinones and their derivatives have been investigated widely due to their physiological and chemotherapeutic properties. Many compounds containing the isoindolinone skeleton have shown antiviral, antileukemic, antiinflammatory, antipsychotic and antiulcer properties (Pendrak et al., 1994; De Clerck, 1995). Isoindolinones are useful for the synthesis of various drugs and naturally occurring compounds (Stowers, 1996; Heaney & Shuhaibar, 1995). In view of this biological importance, the crystal structure of the title compound has been determined and the results are presented here.
Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The isoindole ring system is essentially planar [maximum deviation = 0.019 (2) Å for the N1 atom] and is oriented at a dihedral angle of 51.3 (1)° with respect to the benzene ring. The methyl acrylate (O3/O4/C10–C14) plane forms dihedral angles of 83.2 (1)° and 43.7 (1)°, respectively, with the isoindole and benzene rings. The two methoxy groups at C18 and C17 are almost coplanar with the attached benzene ring as evidenced by torsion angles of C21–O6–C18–C19 = 3.7 (4) and C20–O5–C17–C16 = 4.3 (4)°, respectively. The sum of bond angles around N1 (359.9°) indicates that N1 is in sp2 hybridization. The keto atoms O1 and O2 deviate by 0.034 (2) and -0.004 (2) Å, respectively, from the isoindole ring. The geometric parameters of the title molecule agrees well with those reported for similar structures (Liu et al., 2004, Liang & Li 2006).
The molecular structure is stabilized by C15—H15···O1 intramolecular hydrogen bond, forming S(9) ring motif (Bernstein et al., 1995) (Table 1). In the crystal, the molecules are linked by intermolecular C4—H4···O5i and C4—H4···O6i hydrogen bonds (Table 1; Symmetry code: (i) = 1 + x, y, z)) generating a bifurcated R12(5) ring motif, resulting in an extended one dimensional chains along the b axis (Fig. 2). The crystal packing is further stabilized by π—π interactions with centroid—centroid distances: Cg1—Cg2iii = 3.463 (1) Å and Cg2—Cg1iv = 3.463 (1) Å (Fig. 3; Cg1 and Cg2 are the centroids of N1/C1/C2/C7/C8 indole ring and C14–C19 benzene ring, respectively, symmetry code as in Fig. 3).