organic compounds
5,6-Dichloro-2-(3-methoxyphenyl)isoindoline-1,3-dione
aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, and bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
*Correspondence e-mail: orhanb@omu.edu.tr
The title compound, C15H9Cl2NO3, crystallizes as an 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 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); Hall et al., (1983; 1987); Srivastava et al. (2001); Abdel-Hafez (2004); Sena et al. (2007).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536808010659/rz2205sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010659/rz2205Isup2.hkl
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).
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.
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).C15H9Cl2NO3 | F(000) = 656 |
Mr = 322.13 | Dx = 1.566 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6123 reflections |
a = 6.8689 (5) Å | θ = 2.0–27.3° |
b = 9.7362 (10) Å | µ = 0.48 mm−1 |
c = 20.4271 (14) Å | T = 296 K |
V = 1366.1 (2) Å3 | Prism, colourless |
Z = 4 | 0.65 × 0.51 × 0.23 mm |
Stoe IPDSII diffractometer | 2687 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2076 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.117 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.0° |
ω scan rotation method | h = −8→8 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −12→10 |
Tmin = 0.685, Tmax = 0.888 | l = −23→25 |
6123 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.071 | w = 1/[σ2(Fo2) + (0.1011P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.169 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 0.63 e Å−3 |
2687 reflections | Δρmin = −0.57 e Å−3 |
192 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.054 (7) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1114 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.43 (13) |
C15H9Cl2NO3 | V = 1366.1 (2) Å3 |
Mr = 322.13 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.8689 (5) Å | µ = 0.48 mm−1 |
b = 9.7362 (10) Å | T = 296 K |
c = 20.4271 (14) Å | 0.65 × 0.51 × 0.23 mm |
Stoe IPDSII diffractometer | 2687 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2076 reflections with I > 2σ(I) |
Tmin = 0.685, Tmax = 0.888 | Rint = 0.117 |
6123 measured reflections |
R[F2 > 2σ(F2)] = 0.071 | H-atom parameters constrained |
wR(F2) = 0.169 | Δρmax = 0.63 e Å−3 |
S = 1.01 | Δρmin = −0.57 e Å−3 |
2687 reflections | Absolute structure: Flack (1983), 1114 Friedel pairs |
192 parameters | Absolute structure parameter: 0.43 (13) |
0 restraints |
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 | ||
C1 | 0.2767 (6) | 0.3976 (4) | 0.4834 (2) | 0.0408 (9) | |
C2 | 0.2607 (6) | 0.5458 (4) | 0.5011 (2) | 0.0380 (8) | |
C3 | 0.2552 (7) | 0.6055 (4) | 0.5626 (2) | 0.0474 (9) | |
H3 | 0.2551 | 0.5526 | 0.6005 | 0.057* | |
C4 | 0.2499 (6) | 0.7459 (4) | 0.5652 (2) | 0.0458 (9) | |
C5 | 0.2520 (6) | 0.8278 (4) | 0.5080 (2) | 0.0444 (9) | |
C6 | 0.2545 (7) | 0.7642 (4) | 0.4471 (2) | 0.0463 (9) | |
H6 | 0.2538 | 0.8157 | 0.4088 | 0.056* | |
C7 | 0.2579 (6) | 0.6225 (4) | 0.44509 (19) | 0.0395 (8) | |
C8 | 0.2677 (6) | 0.5285 (4) | 0.3883 (2) | 0.0438 (9) | |
C9 | 0.3137 (6) | 0.2765 (5) | 0.3758 (2) | 0.0436 (10) | |
C10 | 0.4978 (6) | 0.2535 (6) | 0.3505 (3) | 0.0598 (13) | |
H10 | 0.5993 | 0.3135 | 0.3599 | 0.072* | |
C11 | 0.5282 (7) | 0.1425 (6) | 0.3118 (3) | 0.0624 (14) | |
H11 | 0.6517 | 0.1277 | 0.2946 | 0.075* | |
C12 | 0.3806 (7) | 0.0500 (5) | 0.2972 (2) | 0.0527 (12) | |
H12 | 0.4041 | −0.0263 | 0.2710 | 0.063* | |
C13 | 0.1967 (7) | 0.0752 (5) | 0.3229 (2) | 0.0477 (11) | |
C14 | 0.1630 (6) | 0.1861 (4) | 0.3621 (2) | 0.0466 (10) | |
H14 | 0.0397 | 0.2011 | 0.3795 | 0.056* | |
C15 | 0.0552 (10) | −0.1131 (6) | 0.2632 (3) | 0.0743 (16) | |
H15A | −0.0652 | −0.1629 | 0.2605 | 0.112* | |
H15B | 0.1584 | −0.1749 | 0.2749 | 0.112* | |
H15C | 0.0834 | −0.0720 | 0.2216 | 0.112* | |
N1 | 0.2788 (5) | 0.3963 (4) | 0.41436 (16) | 0.0412 (8) | |
O1 | 0.2907 (5) | 0.2994 (3) | 0.51795 (15) | 0.0550 (8) | |
O2 | 0.2669 (6) | 0.5562 (3) | 0.33082 (15) | 0.0616 (9) | |
O3 | 0.0389 (5) | −0.0085 (4) | 0.3116 (2) | 0.0749 (11) | |
Cl1 | 0.2389 (2) | 0.82582 (13) | 0.64049 (6) | 0.0730 (4) | |
Cl2 | 0.25735 (16) | 1.00342 (11) | 0.51245 (6) | 0.0578 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.047 (2) | 0.0320 (19) | 0.044 (2) | −0.0019 (18) | 0.0005 (19) | 0.0014 (16) |
C2 | 0.0407 (16) | 0.0300 (17) | 0.043 (2) | −0.0036 (16) | −0.0006 (19) | −0.0017 (14) |
C3 | 0.058 (2) | 0.041 (2) | 0.043 (2) | 0.004 (2) | −0.004 (2) | −0.0045 (17) |
C4 | 0.0455 (19) | 0.044 (2) | 0.047 (2) | 0.003 (2) | −0.006 (2) | −0.0117 (17) |
C5 | 0.0383 (15) | 0.0338 (19) | 0.061 (2) | 0.0010 (17) | −0.006 (2) | −0.0052 (18) |
C6 | 0.0487 (19) | 0.037 (2) | 0.053 (2) | 0.006 (2) | 0.001 (2) | 0.0073 (17) |
C7 | 0.0399 (17) | 0.0360 (19) | 0.043 (2) | −0.0027 (18) | 0.001 (2) | 0.0000 (15) |
C8 | 0.049 (2) | 0.041 (2) | 0.042 (2) | 0.004 (2) | 0.0003 (18) | 0.0012 (16) |
C9 | 0.054 (2) | 0.043 (2) | 0.034 (2) | 0.0034 (19) | 0.0016 (15) | 0.0006 (18) |
C10 | 0.050 (2) | 0.072 (3) | 0.058 (3) | −0.006 (2) | 0.007 (2) | −0.016 (3) |
C11 | 0.057 (3) | 0.069 (4) | 0.061 (3) | 0.007 (3) | 0.010 (2) | −0.010 (3) |
C12 | 0.075 (3) | 0.043 (3) | 0.040 (3) | 0.012 (2) | 0.002 (2) | −0.011 (2) |
C13 | 0.066 (3) | 0.035 (2) | 0.042 (2) | −0.0022 (19) | −0.0012 (18) | −0.0046 (18) |
C14 | 0.054 (2) | 0.040 (2) | 0.046 (2) | 0.0013 (19) | 0.0058 (18) | −0.001 (2) |
C15 | 0.108 (4) | 0.059 (3) | 0.055 (3) | −0.021 (3) | −0.001 (3) | −0.013 (3) |
N1 | 0.0523 (19) | 0.0362 (17) | 0.0351 (18) | −0.0028 (15) | 0.0025 (15) | −0.0036 (13) |
O1 | 0.087 (2) | 0.0336 (15) | 0.0445 (17) | 0.0030 (16) | −0.0010 (15) | 0.0009 (12) |
O2 | 0.090 (2) | 0.0525 (18) | 0.0425 (18) | 0.004 (2) | 0.0015 (18) | 0.0047 (14) |
O3 | 0.081 (2) | 0.067 (2) | 0.076 (3) | −0.026 (2) | 0.0145 (19) | −0.027 (2) |
Cl1 | 0.1007 (9) | 0.0574 (7) | 0.0609 (8) | 0.0176 (8) | −0.0121 (8) | −0.0238 (6) |
Cl2 | 0.0536 (5) | 0.0314 (5) | 0.0883 (8) | 0.0032 (5) | −0.0054 (6) | −0.0070 (5) |
C1—O1 | 1.192 (5) | C9—C10 | 1.384 (6) |
C1—N1 | 1.410 (5) | C9—C14 | 1.387 (6) |
C1—C2 | 1.491 (5) | C9—N1 | 1.428 (5) |
C2—C7 | 1.367 (5) | C10—C11 | 1.355 (7) |
C2—C3 | 1.384 (6) | C10—H10 | 0.9300 |
C3—C4 | 1.368 (6) | C11—C12 | 1.388 (7) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.415 (6) | C12—C13 | 1.390 (6) |
C4—Cl1 | 1.725 (4) | C12—H12 | 0.9300 |
C5—C6 | 1.389 (6) | C13—C14 | 1.364 (6) |
C5—Cl2 | 1.713 (4) | C13—O3 | 1.376 (5) |
C6—C7 | 1.381 (6) | C14—H14 | 0.9300 |
C6—H6 | 0.9300 | C15—O3 | 1.424 (6) |
C7—C8 | 1.479 (6) | C15—H15A | 0.9600 |
C8—O2 | 1.205 (5) | C15—H15B | 0.9600 |
C8—N1 | 1.395 (5) | C15—H15C | 0.9600 |
O1—C1—N1 | 125.7 (4) | C14—C9—N1 | 120.2 (3) |
O1—C1—C2 | 129.6 (4) | C11—C10—C9 | 119.2 (4) |
N1—C1—C2 | 104.6 (3) | C11—C10—H10 | 120.4 |
C7—C2—C3 | 122.0 (4) | C9—C10—H10 | 120.4 |
C7—C2—C1 | 109.0 (3) | C10—C11—C12 | 122.0 (4) |
C3—C2—C1 | 129.0 (4) | C10—C11—H11 | 119.0 |
C4—C3—C2 | 117.1 (4) | C12—C11—H11 | 119.0 |
C4—C3—H3 | 121.5 | C11—C12—C13 | 117.9 (4) |
C2—C3—H3 | 121.5 | C11—C12—H12 | 121.1 |
C3—C4—C5 | 122.0 (4) | C13—C12—H12 | 121.1 |
C3—C4—Cl1 | 119.1 (3) | C14—C13—O3 | 115.7 (4) |
C5—C4—Cl1 | 118.9 (3) | C14—C13—C12 | 121.1 (4) |
C6—C5—C4 | 119.2 (4) | O3—C13—C12 | 123.2 (4) |
C6—C5—Cl2 | 119.5 (3) | C13—C14—C9 | 119.6 (4) |
C4—C5—Cl2 | 121.2 (3) | C13—C14—H14 | 120.2 |
C7—C6—C5 | 118.2 (4) | C9—C14—H14 | 120.2 |
C7—C6—H6 | 120.9 | O3—C15—H15A | 109.5 |
C5—C6—H6 | 120.9 | O3—C15—H15B | 109.5 |
C2—C7—C6 | 121.4 (4) | H15A—C15—H15B | 109.5 |
C2—C7—C8 | 108.6 (3) | O3—C15—H15C | 109.5 |
C6—C7—C8 | 130.0 (4) | H15A—C15—H15C | 109.5 |
O2—C8—N1 | 125.4 (4) | H15B—C15—H15C | 109.5 |
O2—C8—C7 | 128.7 (4) | C8—N1—C1 | 111.9 (3) |
N1—C8—C7 | 105.9 (3) | C8—N1—C9 | 123.5 (3) |
C10—C9—C14 | 120.3 (4) | C1—N1—C9 | 124.1 (3) |
C10—C9—N1 | 119.5 (4) | C13—O3—C15 | 118.6 (4) |
O1—C1—C2—C7 | 176.9 (5) | C14—C9—C10—C11 | 0.5 (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—C13 | 0.8 (8) |
C7—C2—C3—C4 | −1.0 (7) | C11—C12—C13—C14 | −0.9 (7) |
C1—C2—C3—C4 | 176.7 (4) | C11—C12—C13—O3 | 179.7 (5) |
C2—C3—C4—C5 | −0.6 (8) | O3—C13—C14—C9 | −179.7 (4) |
C2—C3—C4—Cl1 | 178.9 (3) | C12—C13—C14—C9 | 0.9 (7) |
C3—C4—C5—C6 | 1.7 (7) | C10—C9—C14—C13 | −0.7 (7) |
Cl1—C4—C5—C6 | −177.9 (4) | N1—C9—C14—C13 | 177.2 (4) |
C3—C4—C5—Cl2 | −176.8 (4) | O2—C8—N1—C1 | 180.0 (5) |
Cl1—C4—C5—Cl2 | 3.6 (5) | C7—C8—N1—C1 | 0.1 (5) |
C4—C5—C6—C7 | −1.0 (7) | O2—C8—N1—C9 | 7.6 (7) |
Cl2—C5—C6—C7 | 177.4 (3) | C7—C8—N1—C9 | −172.3 (4) |
C3—C2—C7—C6 | 1.7 (7) | O1—C1—N1—C8 | −177.5 (4) |
C1—C2—C7—C6 | −176.5 (4) | C2—C1—N1—C8 | 0.6 (5) |
C3—C2—C7—C8 | 179.3 (4) | O1—C1—N1—C9 | −5.2 (7) |
C1—C2—C7—C8 | 1.2 (5) | C2—C1—N1—C9 | 172.9 (3) |
C5—C6—C7—C2 | −0.6 (7) | C10—C9—N1—C8 | 72.8 (6) |
C5—C6—C7—C8 | −177.7 (4) | C14—C9—N1—C8 | −105.2 (5) |
C2—C7—C8—O2 | 179.3 (5) | C10—C9—N1—C1 | −98.6 (5) |
C6—C7—C8—O2 | −3.3 (9) | C14—C9—N1—C1 | 83.4 (5) |
C2—C7—C8—N1 | −0.8 (5) | C14—C13—O3—C15 | 170.2 (5) |
C6—C7—C8—N1 | 176.6 (5) | C12—C13—O3—C15 | −10.5 (8) |
Experimental details
Crystal data | |
Chemical formula | C15H9Cl2NO3 |
Mr | 322.13 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 6.8689 (5), 9.7362 (10), 20.4271 (14) |
V (Å3) | 1366.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.48 |
Crystal size (mm) | 0.65 × 0.51 × 0.23 |
Data collection | |
Diffractometer | Stoe IPDSII diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.685, 0.888 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6123, 2687, 2076 |
Rint | 0.117 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.169, 1.01 |
No. of reflections | 2687 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.63, −0.57 |
Absolute structure | Flack (1983), 1114 Friedel pairs |
Absolute structure parameter | 0.43 (13) |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Acknowledgements
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).
References
Abdel-Hafez, A. A. M. (2004). Arch. Pharm. Res. 27, 495–501. Web of Science PubMed CAS Google Scholar
Chapman, J. M., Cocolas, G. H. & Hall, I. H. (1979). J. Med. Chem. 22, 1399–1402. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hall, I. H., Reynolds, D. J., Wong, O. T., Oswald, C. B. & Murthy, A. R. K. (1987). Pharm. Res. 4, 472–479. CrossRef CAS PubMed Web of Science Google Scholar
Hall, I. H., Voorstad, P. J., Chapman, J. M. & Cocolas, G. H. (1983). J. Pharm. Sci. 72, 845–851. CrossRef CAS PubMed Web of Science Google Scholar
Sena, V. L. M., Srivastava, M. R., de Simone, C. A., da Cruz Gonçalves, S. M., Silva, R. O. & Pereira, M. A. (2007). J. Braz. Chem. Soc. 18, 1224–1234. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Srivastava, R. M., Oliveira, F. J. S., da Silva, L. P., de Freitas Filho, J. R., Oliveira, S. P. & Lima, V. L. M. (2001). Carbohydr. Res. 332, 335–340. Web of Science CrossRef PubMed CAS Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
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.
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.