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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o337.
Published online 2010 January 13. doi:  10.1107/S160053680905524X
PMCID: PMC2979961

Bis[2-(1,3-dioxoisoindolin-2-yl)eth­yl] phthalate

Abstract

The title compound, C28H20N2O8, was synthesized by the reaction of isobenzofuran-1,3-dione and 2-amino­ethanol in a one-pot reaction. The benzene and five-membered rings are slightly twisted to each other, making dihedral angles of 2.77 (9) and 1.77 (10)°. The rings of the phthalimide groups make dihedral angle of 57.64 (7) and 83.46 (7)° with the central benzene ring. Weak C—H(...)O, C—H(...)π and π–π [centroid–centroid distance = 3.446 (1) and 3.599 (1) Å] inter­actions reinforce the cohesion of the crystal.

Related literature

For a related structure, see: Liang & Li (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-66-0o337-scheme1.jpg

Experimental

Crystal data

  • C28H20N2O8
  • M r = 512.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o337-efi1.jpg
  • a = 15.021 (2) Å
  • b = 12.3953 (19) Å
  • c = 25.954 (4) Å
  • β = 90.125 (2)°
  • V = 4832.5 (13) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 295 K
  • 0.33 × 0.27 × 0.12 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.966, T max = 0.988
  • 18257 measured reflections
  • 4718 independent reflections
  • 3689 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.110
  • S = 1.03
  • 4718 reflections
  • 343 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]) and ORTEP-32 (Farrugia, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905524X/dn2524sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905524X/dn2524Isup2.hkl

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

Acknowledgments

This research was supported financially by National Natural Science Foundation of China (30660215).

supplementary crystallographic information

Comment

2-(2-hydroxyethyl)isoindoline-1,3-dione (Liang & Li, 2006) is a useful pharmaceutical intermediate in the synthesis of drugs containing aminoethyl group). The title compound, Bis(2-(1,3-dioxoisoindolin-2-yl)ethyl) phthalate includes two phthalamide groups and then easily provides two aminoethyl groups. As an intermediate for further synthesis, we obtained it in one-pot reaction.

The asymmetric unit is built up from a central phtalate with two pendant dioxoisoindolin groups (Fig. 1). The geometry of both the phthalimide rings compare well with the structure of the 2-(2-hydroxyethyl)isoindoline-1,3-dione (Liang & Li, 2006).

They could be regarded as planar with the largest deviation being 0.033 (2) Å and 0.028 (2) Å for C3 and C21 respectively, although the phenyl and the 5-membered rings are slightly twisted to each other making dihedral angles of 2.77 (9)° and 1.77 (10)° respectively. The phthalimide rings make dihedral angle of 57.64 (7)° and 83.46 (7)° with the central phenyl ring. Bond lengths and angles are normal and comparable to those observed in related compounds (Allen et al., 1987).

Weak C-H···O, C-H···π and π-π interactions reinforce the cohesion of the crystal (Table 1,2).

Experimental

44.5 g of isobenzofuran-1,3-dione (0.3 mol), 12.2 g of 2-aminoethanol (0.2 mol) were mixed in a flask and the mixture was heated up to boiling for one hour and then the reaction mixture was poured into water to give white precipitate. The precipitate was filtered, washed with water and dried in air to give the title compound as white solid (40.13 g, 78%). A little of the white solid was dissolved in mixed acetone/ water (50:1). After standing in air over a period of seven days, the acetone is evaporated, colourless crystals suitable for X-ray diffraction analysis were formed at the bottom of the vessel.

Refinement

All H atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.97 Å (methylene) with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

Crystal data

C28H20N2O8F(000) = 2128
Mr = 512.46Dx = 1.409 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 19894 reflections
a = 15.021 (2) Åθ = 2.3–24.0°
b = 12.3953 (19) ŵ = 0.11 mm1
c = 25.954 (4) ÅT = 295 K
β = 90.125 (2)°Block, colourless
V = 4832.5 (13) Å30.33 × 0.27 × 0.12 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer4718 independent reflections
Radiation source: fine-focus sealed tube3689 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −18→18
Tmin = 0.966, Tmax = 0.988k = −15→15
18257 measured reflectionsl = −32→32

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0561P)2 + 1.0157P] where P = (Fo2 + 2Fc2)/3
4718 reflections(Δ/σ)max = 0.001
343 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.18 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.97630 (11)1.05121 (13)0.91255 (6)0.0416 (4)
C20.97412 (11)0.96188 (13)0.87460 (6)0.0418 (4)
C31.03959 (12)0.89040 (15)0.85964 (7)0.0553 (5)
H31.09730.89570.87240.066*
C41.01605 (15)0.81098 (16)0.82513 (7)0.0650 (5)
H41.05880.76160.81440.078*
C50.93112 (15)0.80299 (16)0.80617 (7)0.0640 (5)
H50.91720.74830.78300.077*
C60.86611 (13)0.87458 (16)0.82088 (6)0.0548 (5)
H60.80860.86950.80780.066*
C70.88892 (10)0.95428 (13)0.85562 (6)0.0400 (4)
C80.83416 (10)1.03777 (13)0.88082 (6)0.0431 (4)
C90.86318 (12)1.18167 (13)0.94637 (6)0.0481 (4)
H9A0.80601.20840.93450.058*
H9B0.90601.23990.94320.058*
C100.85568 (11)1.15007 (13)1.00187 (6)0.0459 (4)
H10A0.91401.13331.01590.055*
H10B0.83011.20851.02180.055*
C110.75624 (10)1.03503 (12)1.04734 (6)0.0388 (4)
C120.70715 (10)0.93102 (12)1.04218 (6)0.0389 (4)
C130.73462 (12)0.84711 (14)1.07294 (6)0.0501 (4)
H130.77710.85901.09840.060*
C140.69920 (14)0.74499 (15)1.06614 (7)0.0579 (5)
H140.71860.68821.08670.069*
C150.63546 (13)0.72739 (15)1.02905 (7)0.0553 (5)
H150.61180.65871.02450.066*
C160.60667 (11)0.81130 (13)0.99856 (7)0.0475 (4)
H160.56330.79910.97360.057*
C170.64183 (10)0.91381 (12)1.00478 (6)0.0382 (4)
C180.60827 (10)1.00635 (13)0.97419 (6)0.0402 (4)
C190.53654 (12)1.06028 (14)0.89801 (6)0.0475 (4)
H19A0.58531.10120.88330.057*
H19B0.49931.10910.91770.057*
C200.48331 (11)1.00681 (15)0.85621 (6)0.0492 (4)
H20A0.43680.96350.87180.059*
H20B0.45501.06180.83530.059*
C210.59113 (10)0.97752 (15)0.78414 (6)0.0430 (4)
C220.63316 (11)0.88163 (14)0.76059 (6)0.0462 (4)
C230.68986 (12)0.87307 (18)0.71912 (7)0.0602 (5)
H230.70770.93360.70060.072*
C240.71909 (14)0.7715 (2)0.70614 (8)0.0773 (7)
H240.75700.76320.67810.093*
C250.69367 (17)0.6827 (2)0.73348 (9)0.0850 (7)
H250.71610.61540.72440.102*
C260.63520 (16)0.69062 (17)0.77446 (8)0.0742 (6)
H260.61690.62990.79260.089*
C270.60526 (12)0.79191 (15)0.78731 (7)0.0518 (4)
C280.54202 (12)0.82721 (15)0.82772 (6)0.0509 (4)
N10.89058 (8)1.09290 (10)0.91377 (5)0.0400 (3)
N20.53736 (9)0.93881 (11)0.82350 (5)0.0434 (3)
O11.03739 (8)1.08221 (10)0.93858 (5)0.0612 (4)
O20.75574 (8)1.05580 (11)0.87512 (5)0.0634 (4)
O30.79903 (7)1.05658 (8)1.00380 (4)0.0446 (3)
O40.76146 (8)1.08763 (10)1.08580 (4)0.0541 (3)
O50.61305 (9)1.09848 (9)0.98776 (5)0.0592 (3)
O60.57008 (8)0.97564 (9)0.93053 (4)0.0485 (3)
O70.59873 (9)1.07155 (10)0.77251 (5)0.0588 (3)
O80.50082 (10)0.77394 (12)0.85785 (5)0.0771 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0395 (9)0.0390 (9)0.0465 (9)−0.0041 (7)0.0018 (7)0.0000 (7)
C20.0435 (9)0.0440 (9)0.0378 (8)−0.0002 (7)0.0015 (7)0.0004 (7)
C30.0521 (10)0.0608 (12)0.0529 (10)0.0127 (9)−0.0041 (8)−0.0104 (9)
C40.0805 (14)0.0626 (13)0.0519 (11)0.0182 (11)0.0013 (10)−0.0143 (9)
C50.0878 (15)0.0625 (13)0.0419 (10)−0.0062 (11)0.0005 (10)−0.0143 (9)
C60.0575 (11)0.0690 (13)0.0378 (9)−0.0113 (9)−0.0049 (8)−0.0031 (8)
C70.0433 (9)0.0447 (9)0.0320 (8)−0.0059 (7)0.0008 (6)0.0047 (7)
C80.0390 (9)0.0513 (10)0.0391 (8)−0.0035 (7)0.0028 (7)0.0112 (7)
C90.0519 (10)0.0333 (9)0.0591 (10)−0.0013 (7)0.0144 (8)−0.0001 (8)
C100.0465 (9)0.0358 (9)0.0554 (10)−0.0100 (7)0.0071 (7)−0.0088 (8)
C110.0385 (8)0.0411 (9)0.0368 (8)0.0018 (7)0.0004 (6)−0.0037 (7)
C120.0421 (8)0.0395 (9)0.0352 (8)−0.0034 (7)0.0096 (7)−0.0016 (7)
C130.0574 (10)0.0518 (11)0.0413 (9)−0.0048 (8)0.0046 (8)0.0062 (8)
C140.0731 (13)0.0459 (11)0.0546 (11)−0.0041 (9)0.0152 (10)0.0147 (9)
C150.0646 (12)0.0402 (10)0.0612 (11)−0.0135 (9)0.0191 (9)−0.0008 (8)
C160.0468 (9)0.0438 (10)0.0519 (10)−0.0098 (8)0.0090 (8)−0.0076 (8)
C170.0383 (8)0.0381 (9)0.0383 (8)−0.0036 (7)0.0095 (6)−0.0054 (7)
C180.0359 (8)0.0421 (9)0.0425 (8)−0.0019 (7)0.0047 (6)−0.0087 (7)
C190.0502 (10)0.0470 (10)0.0452 (9)0.0074 (8)0.0007 (8)−0.0030 (8)
C200.0397 (9)0.0619 (11)0.0460 (9)0.0061 (8)0.0016 (7)−0.0046 (8)
C210.0392 (8)0.0531 (11)0.0366 (8)−0.0003 (7)−0.0047 (7)0.0014 (8)
C220.0400 (9)0.0600 (11)0.0384 (8)0.0027 (8)−0.0047 (7)−0.0034 (8)
C230.0461 (10)0.0896 (15)0.0448 (10)0.0032 (10)0.0008 (8)−0.0081 (10)
C240.0588 (13)0.116 (2)0.0570 (12)0.0185 (13)0.0028 (10)−0.0264 (13)
C250.0870 (17)0.0921 (19)0.0758 (15)0.0372 (14)−0.0090 (13)−0.0328 (14)
C260.0930 (16)0.0588 (13)0.0709 (14)0.0133 (12)−0.0080 (12)−0.0075 (11)
C270.0551 (10)0.0538 (11)0.0465 (9)0.0073 (9)−0.0039 (8)−0.0060 (8)
C280.0574 (11)0.0528 (11)0.0424 (9)−0.0031 (9)0.0002 (8)0.0036 (8)
N10.0381 (7)0.0356 (7)0.0463 (7)−0.0017 (6)0.0074 (6)0.0001 (6)
N20.0437 (7)0.0488 (8)0.0378 (7)0.0009 (6)0.0018 (6)−0.0028 (6)
O10.0471 (7)0.0623 (8)0.0743 (9)−0.0038 (6)−0.0092 (6)−0.0211 (7)
O20.0369 (7)0.0902 (10)0.0630 (8)0.0056 (6)0.0004 (6)0.0048 (7)
O30.0530 (7)0.0394 (6)0.0414 (6)−0.0135 (5)0.0080 (5)−0.0058 (5)
O40.0636 (8)0.0564 (8)0.0423 (6)−0.0081 (6)0.0030 (6)−0.0149 (6)
O50.0736 (9)0.0393 (7)0.0647 (8)0.0074 (6)−0.0174 (7)−0.0136 (6)
O60.0586 (7)0.0444 (7)0.0424 (6)−0.0010 (5)−0.0060 (5)−0.0055 (5)
O70.0657 (8)0.0527 (8)0.0579 (8)−0.0033 (6)0.0015 (6)0.0094 (6)
O80.0953 (11)0.0665 (9)0.0696 (9)−0.0120 (8)0.0211 (8)0.0121 (7)

Geometric parameters (Å, °)

C1—O11.2014 (19)C14—H140.9300
C1—N11.388 (2)C15—C161.376 (2)
C1—C21.482 (2)C15—H150.9300
C2—C71.374 (2)C16—C171.385 (2)
C2—C31.380 (2)C16—H160.9300
C3—C41.377 (3)C17—C181.483 (2)
C3—H30.9300C18—O51.1972 (18)
C4—C51.370 (3)C18—O61.3250 (18)
C4—H40.9300C19—O61.437 (2)
C5—C61.374 (3)C19—C201.501 (2)
C5—H50.9300C19—H19A0.9700
C6—C71.380 (2)C19—H19B0.9700
C6—H60.9300C20—N21.447 (2)
C7—C81.476 (2)C20—H20A0.9700
C8—O21.2077 (19)C20—H20B0.9700
C8—N11.383 (2)C21—O71.209 (2)
C9—N11.448 (2)C21—N21.389 (2)
C9—C101.497 (2)C21—C221.479 (2)
C9—H9A0.9700C22—C271.376 (2)
C9—H9B0.9700C22—C231.378 (2)
C10—O31.4387 (18)C23—C241.375 (3)
C10—H10A0.9700C23—H230.9300
C10—H10B0.9700C24—C251.365 (4)
C11—O41.1947 (18)C24—H240.9300
C11—O31.3284 (18)C25—C261.384 (3)
C11—C121.491 (2)C25—H250.9300
C12—C131.374 (2)C26—C271.375 (3)
C12—C171.395 (2)C26—H260.9300
C13—C141.384 (3)C27—C281.483 (2)
C13—H130.9300C28—O81.197 (2)
C14—C151.374 (3)C28—N21.389 (2)
O1—C1—N1125.14 (15)C15—C16—H16119.8
O1—C1—C2128.94 (16)C17—C16—H16119.8
N1—C1—C2105.91 (13)C16—C17—C12119.25 (15)
C7—C2—C3121.28 (15)C16—C17—C18121.21 (15)
C7—C2—C1107.98 (14)C12—C17—C18119.48 (14)
C3—C2—C1130.67 (16)O5—C18—O6123.45 (15)
C4—C3—C2117.38 (18)O5—C18—C17124.08 (14)
C4—C3—H3121.3O6—C18—C17112.45 (13)
C2—C3—H3121.3O6—C19—C20106.72 (14)
C5—C4—C3121.54 (18)O6—C19—H19A110.4
C5—C4—H4119.2C20—C19—H19A110.4
C3—C4—H4119.2O6—C19—H19B110.4
C4—C5—C6121.02 (17)C20—C19—H19B110.4
C4—C5—H5119.5H19A—C19—H19B108.6
C6—C5—H5119.5N2—C20—C19112.51 (13)
C5—C6—C7117.91 (17)N2—C20—H20A109.1
C5—C6—H6121.0C19—C20—H20A109.1
C7—C6—H6121.0N2—C20—H20B109.1
C2—C7—C6120.87 (16)C19—C20—H20B109.1
C2—C7—C8108.23 (13)H20A—C20—H20B107.8
C6—C7—C8130.82 (15)O7—C21—N2124.87 (16)
O2—C8—N1125.48 (16)O7—C21—C22129.12 (16)
O2—C8—C7128.31 (16)N2—C21—C22106.00 (15)
N1—C8—C7106.20 (13)C27—C22—C23121.37 (17)
N1—C9—C10112.68 (13)C27—C22—C21108.09 (15)
N1—C9—H9A109.1C23—C22—C21130.53 (18)
C10—C9—H9A109.1C24—C23—C22117.4 (2)
N1—C9—H9B109.1C24—C23—H23121.3
C10—C9—H9B109.1C22—C23—H23121.3
H9A—C9—H9B107.8C25—C24—C23121.4 (2)
O3—C10—C9106.85 (13)C25—C24—H24119.3
O3—C10—H10A110.4C23—C24—H24119.3
C9—C10—H10A110.4C24—C25—C26121.4 (2)
O3—C10—H10B110.4C24—C25—H25119.3
C9—C10—H10B110.4C26—C25—H25119.3
H10A—C10—H10B108.6C27—C26—C25117.4 (2)
O4—C11—O3124.75 (15)C27—C26—H26121.3
O4—C11—C12125.33 (15)C25—C26—H26121.3
O3—C11—C12109.74 (12)C26—C27—C22121.03 (18)
C13—C12—C17119.89 (15)C26—C27—C28130.66 (19)
C13—C12—C11117.04 (15)C22—C27—C28108.31 (15)
C17—C12—C11122.78 (14)O8—C28—N2125.08 (17)
C12—C13—C14120.22 (17)O8—C28—C27129.23 (18)
C12—C13—H13119.9N2—C28—C27105.69 (15)
C14—C13—H13119.9C8—N1—C1111.67 (13)
C15—C14—C13120.12 (17)C8—N1—C9124.20 (13)
C15—C14—H14119.9C1—N1—C9124.13 (13)
C13—C14—H14119.9C21—N2—C28111.88 (14)
C14—C15—C16120.04 (16)C21—N2—C20123.93 (15)
C14—C15—H15120.0C28—N2—C20124.20 (14)
C16—C15—H15120.0C11—O3—C10118.61 (12)
C15—C16—C17120.47 (17)C18—O6—C19116.31 (12)

Hydrogen-bond geometry (Å, °)

Cg4 is the and Cg5 are the centroids of the C12–C17 and C22–C27 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.932.393.315 (2)174
C10—H10B···O5ii0.972.553.163 (2)121
C6—H6···Cg50.932.913.784 (2)167
C19—H19B···Cg4iii0.972.933.817 (2)152

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+3/2, −y+5/2, −z+2; (iii) −x+1, −y+2, −z+2.

Table 2 π–π interactions in (I)

Cg2 is the centroid of the N2/C21/C22/C27/C28 plane and Cg4 is the centroid of the C12–C17 phenyl ring

CgI—CgIICg–Cg (Å)Cg—perp (Å)Offset (°)Symmetry
Cg2—Cg23.446 (1)3.427.04(1-x, y, 1/2-z)
Cg4—Cg43.599 (1)3.35521.2(1/2-x, 1/2-y, -z)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2524).

References

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