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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o881.
Published online 2008 April 23. doi:  10.1107/S1600536808010659
PMCID: PMC2961109

5,6-Dichloro-2-(3-methoxy­phen­yl)isoindoline-1,3-dione

Abstract

The title compound, C15H9Cl2NO3, crystallizes as an inversion twin, the ratio of the twin components being 0.43 (13):0.57 (13). The isoindoline group is planar and inclined by 77.63 (3)° to the aromatic ring substituent. The crystal structure is stabilized by aromatic π–π stacking inter­actions involving the benzene rings of adjacent isoindoline groups, with a centroid–centroid distance of 3.664 (7) Å and an inter­planar separation of 3.409 Å.

Related literature

For general background, see: Chapman et al. (1979 [triangle]); Hall et al., (1983 [triangle]; 1987 [triangle]); Srivastava et al. (2001 [triangle]); Abdel-Hafez (2004 [triangle]); Sena et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o881-scheme1.jpg

Experimental

Crystal data

  • C15H9Cl2NO3
  • M r = 322.13
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o881-efi2.jpg
  • a = 6.8689 (5) Å
  • b = 9.7362 (10) Å
  • c = 20.4271 (14) Å
  • V = 1366.1 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.48 mm−1
  • T = 296 K
  • 0.65 × 0.51 × 0.23 mm

Data collection

  • Stoe IPDSII diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.685, T max = 0.888
  • 6123 measured reflections
  • 2687 independent reflections
  • 2076 reflections with I > 2σ(I)
  • R int = 0.117

Refinement

  • R[F 2 > 2σ(F 2)] = 0.071
  • wR(F 2) = 0.169
  • S = 1.00
  • 2687 reflections
  • 192 parameters
  • H-atom parameters constrained
  • Δρmax = 0.63 e Å−3
  • Δρmin = −0.57 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1114 Friedel pairs
  • Flack parameter: 0.43 (13)

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010659/rz2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010659/rz2205Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

The present work is part of a structural study of derivatives of N-arylphthalimides (Abdel-Hafez, 2004; Chapman et al., 1979; Hall et al., 1983; Hall et al., 1987; Sena et al., 2007; Srivastava et al., 2001). We report here the crystal structure of 5,6-dichloro-2-(3-methoxyphenyl)isoindoline-1,3-dione.

The molecule of the title compound consist of a 5,6-dichlorophthalimide unit connected to a m-methoxyphenyl group through the nitrogen atom (Fig. 1). The isoindoline ring (atoms N1/C1–C8) is almost planar, the largest deviation from the mean plane being 0.051 (3) Å for atom C5. The dihedral angle between the methoxyphenyl ring and the mean plane of the isoindoline group is 77.63 (3)°. The crystal packing is stabilized by aromatic π···π stacking interactions (Fig. 2) occurring between the aromatic rings of isoindoline groups at (x, y, z) and (-1/2+x; 3/2 - y; 1-z), with a centroid-centroid distance of 3.664 (7) Å and a plane-plane separations of 3.409 Å.

Experimental

A mixture of 4,5-dichlorophthalic acid (1.175 g, 0.005 mol) and 2-aminophenol (0.545 g, 0.02 mol) in DMF (1.5 ml) was heated at boiling temperature for 15 min, then ethanol (95%, 50 ml) was added. Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of this mixture at room temperature (yield 80%; mp. 546–548 K).

Refinement

H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. The rather high Rint value is ascribed to the poor nature of the available crystals.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A partial packing diagram of the title compound, showing the formation of π···π stacking interactions. H atoms are omitted for clarity. Cg1 and Cg1i are the centroids of the benzene rings of the isoindoline groups. ...

Crystal data

C15H9Cl2NO3F000 = 656
Mr = 322.13Dx = 1.566 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6123 reflections
a = 6.8689 (5) Åθ = 2.0–27.3º
b = 9.7362 (10) ŵ = 0.48 mm1
c = 20.4271 (14) ÅT = 296 K
V = 1366.1 (2) Å3Prism, colourless
Z = 40.65 × 0.51 × 0.23 mm

Data collection

Stoe IPDSII diffractometer2687 independent reflections
Monochromator: plane graphite2076 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.117
T = 296 Kθmax = 26.0º
ω scan rotation methodθmin = 2.0º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)h = −8→8
Tmin = 0.685, Tmax = 0.888k = −12→10
6123 measured reflectionsl = −23→25

Refinement

Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.1011P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.071(Δ/σ)max = 0.001
wR(F2) = 0.169Δρmax = 0.63 e Å3
S = 1.01Δρmin = −0.57 e Å3
2687 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
192 parametersExtinction coefficient: 0.054 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1114 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.43 (13)
Hydrogen site location: inferred from neighbouring sites

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
C10.2767 (6)0.3976 (4)0.4834 (2)0.0408 (9)
C20.2607 (6)0.5458 (4)0.5011 (2)0.0380 (8)
C30.2552 (7)0.6055 (4)0.5626 (2)0.0474 (9)
H30.25510.55260.60050.057*
C40.2499 (6)0.7459 (4)0.5652 (2)0.0458 (9)
C50.2520 (6)0.8278 (4)0.5080 (2)0.0444 (9)
C60.2545 (7)0.7642 (4)0.4471 (2)0.0463 (9)
H60.25380.81570.40880.056*
C70.2579 (6)0.6225 (4)0.44509 (19)0.0395 (8)
C80.2677 (6)0.5285 (4)0.3883 (2)0.0438 (9)
C90.3137 (6)0.2765 (5)0.3758 (2)0.0436 (10)
C100.4978 (6)0.2535 (6)0.3505 (3)0.0598 (13)
H100.59930.31350.35990.072*
C110.5282 (7)0.1425 (6)0.3118 (3)0.0624 (14)
H110.65170.12770.29460.075*
C120.3806 (7)0.0500 (5)0.2972 (2)0.0527 (12)
H120.4041−0.02630.27100.063*
C130.1967 (7)0.0752 (5)0.3229 (2)0.0477 (11)
C140.1630 (6)0.1861 (4)0.3621 (2)0.0466 (10)
H140.03970.20110.37950.056*
C150.0552 (10)−0.1131 (6)0.2632 (3)0.0743 (16)
H15A−0.0652−0.16290.26050.112*
H15B0.1584−0.17490.27490.112*
H15C0.0834−0.07200.22160.112*
N10.2788 (5)0.3963 (4)0.41436 (16)0.0412 (8)
O10.2907 (5)0.2994 (3)0.51795 (15)0.0550 (8)
O20.2669 (6)0.5562 (3)0.33082 (15)0.0616 (9)
O30.0389 (5)−0.0085 (4)0.3116 (2)0.0749 (11)
Cl10.2389 (2)0.82582 (13)0.64049 (6)0.0730 (4)
Cl20.25735 (16)1.00342 (11)0.51245 (6)0.0578 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.047 (2)0.0320 (19)0.044 (2)−0.0019 (18)0.0005 (19)0.0014 (16)
C20.0407 (16)0.0300 (17)0.043 (2)−0.0036 (16)−0.0006 (19)−0.0017 (14)
C30.058 (2)0.041 (2)0.043 (2)0.004 (2)−0.004 (2)−0.0045 (17)
C40.0455 (19)0.044 (2)0.047 (2)0.003 (2)−0.006 (2)−0.0117 (17)
C50.0383 (15)0.0338 (19)0.061 (2)0.0010 (17)−0.006 (2)−0.0052 (18)
C60.0487 (19)0.037 (2)0.053 (2)0.006 (2)0.001 (2)0.0073 (17)
C70.0399 (17)0.0360 (19)0.043 (2)−0.0027 (18)0.001 (2)0.0000 (15)
C80.049 (2)0.041 (2)0.042 (2)0.004 (2)0.0003 (18)0.0012 (16)
C90.054 (2)0.043 (2)0.034 (2)0.0034 (19)0.0016 (15)0.0006 (18)
C100.050 (2)0.072 (3)0.058 (3)−0.006 (2)0.007 (2)−0.016 (3)
C110.057 (3)0.069 (4)0.061 (3)0.007 (3)0.010 (2)−0.010 (3)
C120.075 (3)0.043 (3)0.040 (3)0.012 (2)0.002 (2)−0.011 (2)
C130.066 (3)0.035 (2)0.042 (2)−0.0022 (19)−0.0012 (18)−0.0046 (18)
C140.054 (2)0.040 (2)0.046 (2)0.0013 (19)0.0058 (18)−0.001 (2)
C150.108 (4)0.059 (3)0.055 (3)−0.021 (3)−0.001 (3)−0.013 (3)
N10.0523 (19)0.0362 (17)0.0351 (18)−0.0028 (15)0.0025 (15)−0.0036 (13)
O10.087 (2)0.0336 (15)0.0445 (17)0.0030 (16)−0.0010 (15)0.0009 (12)
O20.090 (2)0.0525 (18)0.0425 (18)0.004 (2)0.0015 (18)0.0047 (14)
O30.081 (2)0.067 (2)0.076 (3)−0.026 (2)0.0145 (19)−0.027 (2)
Cl10.1007 (9)0.0574 (7)0.0609 (8)0.0176 (8)−0.0121 (8)−0.0238 (6)
Cl20.0536 (5)0.0314 (5)0.0883 (8)0.0032 (5)−0.0054 (6)−0.0070 (5)

Geometric parameters (Å, °)

C1—O11.192 (5)C9—C101.384 (6)
C1—N11.410 (5)C9—C141.387 (6)
C1—C21.491 (5)C9—N11.428 (5)
C2—C71.367 (5)C10—C111.355 (7)
C2—C31.384 (6)C10—H100.9300
C3—C41.368 (6)C11—C121.388 (7)
C3—H30.9300C11—H110.9300
C4—C51.415 (6)C12—C131.390 (6)
C4—Cl11.725 (4)C12—H120.9300
C5—C61.389 (6)C13—C141.364 (6)
C5—Cl21.713 (4)C13—O31.376 (5)
C6—C71.381 (6)C14—H140.9300
C6—H60.9300C15—O31.424 (6)
C7—C81.479 (6)C15—H15A0.9600
C8—O21.205 (5)C15—H15B0.9600
C8—N11.395 (5)C15—H15C0.9600
O1—C1—N1125.7 (4)C14—C9—N1120.2 (3)
O1—C1—C2129.6 (4)C11—C10—C9119.2 (4)
N1—C1—C2104.6 (3)C11—C10—H10120.4
C7—C2—C3122.0 (4)C9—C10—H10120.4
C7—C2—C1109.0 (3)C10—C11—C12122.0 (4)
C3—C2—C1129.0 (4)C10—C11—H11119.0
C4—C3—C2117.1 (4)C12—C11—H11119.0
C4—C3—H3121.5C11—C12—C13117.9 (4)
C2—C3—H3121.5C11—C12—H12121.1
C3—C4—C5122.0 (4)C13—C12—H12121.1
C3—C4—Cl1119.1 (3)C14—C13—O3115.7 (4)
C5—C4—Cl1118.9 (3)C14—C13—C12121.1 (4)
C6—C5—C4119.2 (4)O3—C13—C12123.2 (4)
C6—C5—Cl2119.5 (3)C13—C14—C9119.6 (4)
C4—C5—Cl2121.2 (3)C13—C14—H14120.2
C7—C6—C5118.2 (4)C9—C14—H14120.2
C7—C6—H6120.9O3—C15—H15A109.5
C5—C6—H6120.9O3—C15—H15B109.5
C2—C7—C6121.4 (4)H15A—C15—H15B109.5
C2—C7—C8108.6 (3)O3—C15—H15C109.5
C6—C7—C8130.0 (4)H15A—C15—H15C109.5
O2—C8—N1125.4 (4)H15B—C15—H15C109.5
O2—C8—C7128.7 (4)C8—N1—C1111.9 (3)
N1—C8—C7105.9 (3)C8—N1—C9123.5 (3)
C10—C9—C14120.3 (4)C1—N1—C9124.1 (3)
C10—C9—N1119.5 (4)C13—O3—C15118.6 (4)
O1—C1—C2—C7176.9 (5)C14—C9—C10—C110.5 (8)
N1—C1—C2—C7−1.1 (5)N1—C9—C10—C11−177.4 (4)
O1—C1—C2—C3−1.1 (8)C9—C10—C11—C12−0.6 (9)
N1—C1—C2—C3−179.1 (4)C10—C11—C12—C130.8 (8)
C7—C2—C3—C4−1.0 (7)C11—C12—C13—C14−0.9 (7)
C1—C2—C3—C4176.7 (4)C11—C12—C13—O3179.7 (5)
C2—C3—C4—C5−0.6 (8)O3—C13—C14—C9−179.7 (4)
C2—C3—C4—Cl1178.9 (3)C12—C13—C14—C90.9 (7)
C3—C4—C5—C61.7 (7)C10—C9—C14—C13−0.7 (7)
Cl1—C4—C5—C6−177.9 (4)N1—C9—C14—C13177.2 (4)
C3—C4—C5—Cl2−176.8 (4)O2—C8—N1—C1180.0 (5)
Cl1—C4—C5—Cl23.6 (5)C7—C8—N1—C10.1 (5)
C4—C5—C6—C7−1.0 (7)O2—C8—N1—C97.6 (7)
Cl2—C5—C6—C7177.4 (3)C7—C8—N1—C9−172.3 (4)
C3—C2—C7—C61.7 (7)O1—C1—N1—C8−177.5 (4)
C1—C2—C7—C6−176.5 (4)C2—C1—N1—C80.6 (5)
C3—C2—C7—C8179.3 (4)O1—C1—N1—C9−5.2 (7)
C1—C2—C7—C81.2 (5)C2—C1—N1—C9172.9 (3)
C5—C6—C7—C2−0.6 (7)C10—C9—N1—C872.8 (6)
C5—C6—C7—C8−177.7 (4)C14—C9—N1—C8−105.2 (5)
C2—C7—C8—O2179.3 (5)C10—C9—N1—C1−98.6 (5)
C6—C7—C8—O2−3.3 (9)C14—C9—N1—C183.4 (5)
C2—C7—C8—N1−0.8 (5)C14—C13—O3—C15170.2 (5)
C6—C7—C8—N1176.6 (5)C12—C13—O3—C15−10.5 (8)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2205).

References

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