Acta Cryst. (2007). E63, o3694 [ doi:10.1107/S1600536807037038 ]
In the title compound, C22H12N2O4, the two isoindolinyl groups are twisted with respect to the benzene ring, with dihedral angles of 58.15 (7) and 61.32 (7)°; the dihedral angle between the two isoindolinyl groups is 39.45 (6)°. The molecules are linked together by weak C-H
O hydrogen bonding.
O-Phenylenediamine (0.11 g, 1 mmol) was dissolved in 5 ml glacial acetic acid, and a solution of phthalic anhydride (0.148 g, 1 mmol) in 10 ml of glacial acetic acid was added. After 30 min, the mixture was diluted with cool water, and then the grey precipitate was separated and then refluxed in dry benzene (20 ml) for 4 h using Dean and Stark apparatus. After solvent was removed under reduced pressure the solid product was obtained. The colorless single crystals of the title compound were obtained by recrystallization from an ethanol solution at room temperature after 2 d.
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXTL-Plus.
![[Figure 1]](./xu2298fig1thm.gif)
| Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 50% probability level. |
| C22H12N2O4 | F000 = 760 |
| Mr = 368.34 | Dx = 1.385 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 9771 reflections |
| a = 10.7765 (10) Å | θ = 2.2–26.0º |
| b = 16.9259 (17) Å | µ = 0.10 mm−1 |
| c = 10.8518 (10) Å | T = 293 (2) K |
| β = 116.780 (1)º | Block, colourless |
| V = 1767.1 (3) Å3 | 0.35 × 0.33 × 0.28 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 2553 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.050 |
| Monochromator: graphite | θmax = 26.0º |
| T = 293(2) K | θmin = 2.2º |
| φ and ω scans | h = −9→13 |
| Absorption correction: none | k = −16→20 |
| 9771 measured reflections | l = −13→13 |
| 3476 independent 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)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0421P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.95 | (Δ/σ)max = 0.001 |
| 3476 reflections | Δρmax = 0.20 e Å−3 |
| 253 parameters | Δρmin = −0.19 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C22H12N2O4 | V = 1767.1 (3) Å3 |
| Mr = 368.34 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 10.7765 (10) Å | µ = 0.10 mm−1 |
| b = 16.9259 (17) Å | T = 293 (2) K |
| c = 10.8518 (10) Å | 0.35 × 0.33 × 0.28 mm |
| β = 116.780 (1)º |
| Bruker SMART CCD area-detector diffractometer | 3476 independent reflections |
| Absorption correction: none | 2553 reflections with I > 2σ(I) |
| 9771 measured reflections | Rint = 0.050 |
| R[F2 > 2σ(F2)] = 0.041 | 253 parameters |
| wR(F2) = 0.094 | H-atom parameters constrained |
| S = 0.95 | Δρmax = 0.20 e Å−3 |
| 3476 reflections | Δρmin = −0.19 e Å−3 |
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 > 2sigma(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 | ||
| O1 | 0.45581 (11) | 0.01749 (7) | 0.14315 (11) | 0.0365 (3) | |
| O2 | 0.07744 (11) | 0.13152 (8) | 0.15937 (12) | 0.0437 (4) | |
| O3 | 0.74820 (11) | 0.10013 (7) | 0.38688 (11) | 0.0322 (3) | |
| O4 | 0.34849 (12) | 0.24241 (7) | 0.14859 (13) | 0.0411 (3) | |
| N1 | 0.28632 (13) | 0.07596 (8) | 0.18964 (12) | 0.0264 (3) | |
| N2 | 0.53713 (12) | 0.16715 (8) | 0.29363 (13) | 0.0257 (3) | |
| C1 | 0.34000 (17) | 0.04363 (10) | 0.10366 (16) | 0.0277 (4) | |
| C2 | 0.14769 (16) | 0.10141 (10) | 0.11178 (16) | 0.0296 (4) | |
| C3 | 0.66539 (16) | 0.14316 (10) | 0.29978 (16) | 0.0252 (4) | |
| C4 | 0.46318 (17) | 0.21605 (10) | 0.17971 (16) | 0.0296 (4) | |
| C11 | 0.36534 (16) | 0.09109 (10) | 0.33430 (15) | 0.0250 (4) | |
| C12 | 0.48509 (16) | 0.13677 (10) | 0.38461 (16) | 0.0251 (4) | |
| C13 | 0.55851 (17) | 0.15123 (10) | 0.52504 (16) | 0.0312 (4) | |
| H13A | 0.6389 | 0.1817 | 0.5587 | 0.037* | |
| C14 | 0.51259 (18) | 0.12054 (11) | 0.61507 (17) | 0.0339 (4) | |
| H14A | 0.5619 | 0.1304 | 0.7092 | 0.041* | |
| C15 | 0.39354 (18) | 0.07529 (11) | 0.56535 (16) | 0.0336 (4) | |
| H15A | 0.3629 | 0.0544 | 0.6261 | 0.040* | |
| C16 | 0.31966 (17) | 0.06088 (10) | 0.42531 (16) | 0.0301 (4) | |
| H16A | 0.2389 | 0.0307 | 0.3921 | 0.036* | |
| C21 | 0.22647 (16) | 0.05014 (10) | −0.03928 (15) | 0.0268 (4) | |
| C22 | 0.11188 (16) | 0.08397 (10) | −0.03443 (16) | 0.0283 (4) | |
| C23 | −0.00825 (18) | 0.09885 (11) | −0.15363 (17) | 0.0352 (4) | |
| H23A | −0.0856 | 0.1211 | −0.1505 | 0.042* | |
| C24 | −0.00952 (18) | 0.07944 (11) | −0.27824 (17) | 0.0374 (4) | |
| H24A | −0.0890 | 0.0892 | −0.3602 | 0.045* | |
| C25 | 0.10523 (18) | 0.04581 (11) | −0.28296 (17) | 0.0388 (5) | |
| H25A | 0.1015 | 0.0332 | −0.3680 | 0.047* | |
| C26 | 0.22624 (18) | 0.03050 (11) | −0.16251 (16) | 0.0347 (4) | |
| H26A | 0.3037 | 0.0079 | −0.1652 | 0.042* | |
| C31 | 0.67265 (16) | 0.18160 (10) | 0.18068 (15) | 0.0270 (4) | |
| C32 | 0.55298 (16) | 0.22536 (10) | 0.10967 (16) | 0.0295 (4) | |
| C33 | 0.53101 (18) | 0.26772 (11) | −0.00715 (18) | 0.0392 (5) | |
| H33A | 0.4505 | 0.2973 | −0.0546 | 0.047* | |
| C34 | 0.63355 (19) | 0.26451 (12) | −0.05105 (18) | 0.0429 (5) | |
| H34A | 0.6214 | 0.2921 | −0.1298 | 0.051* | |
| C35 | 0.75357 (19) | 0.22099 (11) | 0.02044 (18) | 0.0388 (5) | |
| H35A | 0.8211 | 0.2203 | −0.0107 | 0.047* | |
| C36 | 0.77526 (17) | 0.17830 (11) | 0.13755 (17) | 0.0327 (4) | |
| H36A | 0.8556 | 0.1487 | 0.1851 | 0.039* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0277 (7) | 0.0500 (8) | 0.0315 (6) | 0.0109 (6) | 0.0132 (5) | −0.0002 (6) |
| O2 | 0.0273 (7) | 0.0680 (10) | 0.0370 (7) | 0.0069 (6) | 0.0156 (6) | −0.0122 (6) |
| O3 | 0.0240 (6) | 0.0402 (8) | 0.0282 (6) | 0.0050 (6) | 0.0082 (5) | 0.0051 (5) |
| O4 | 0.0267 (7) | 0.0422 (8) | 0.0558 (8) | 0.0104 (6) | 0.0199 (6) | 0.0156 (6) |
| N1 | 0.0210 (7) | 0.0358 (8) | 0.0233 (7) | 0.0002 (6) | 0.0107 (6) | −0.0034 (6) |
| N2 | 0.0197 (7) | 0.0312 (8) | 0.0268 (7) | 0.0019 (6) | 0.0112 (6) | 0.0054 (6) |
| C1 | 0.0277 (9) | 0.0297 (10) | 0.0280 (9) | 0.0000 (8) | 0.0145 (8) | −0.0010 (7) |
| C2 | 0.0228 (9) | 0.0361 (11) | 0.0305 (9) | −0.0017 (8) | 0.0124 (8) | −0.0034 (8) |
| C3 | 0.0198 (8) | 0.0288 (10) | 0.0254 (8) | −0.0027 (7) | 0.0087 (7) | −0.0018 (7) |
| C4 | 0.0247 (9) | 0.0293 (10) | 0.0339 (9) | 0.0008 (8) | 0.0123 (8) | 0.0039 (8) |
| C11 | 0.0224 (9) | 0.0304 (10) | 0.0223 (8) | 0.0031 (7) | 0.0101 (7) | −0.0011 (7) |
| C12 | 0.0225 (8) | 0.0281 (9) | 0.0260 (8) | 0.0024 (7) | 0.0122 (7) | 0.0019 (7) |
| C13 | 0.0247 (9) | 0.0353 (11) | 0.0299 (9) | −0.0026 (8) | 0.0090 (8) | −0.0035 (8) |
| C14 | 0.0342 (10) | 0.0432 (12) | 0.0220 (8) | 0.0019 (9) | 0.0107 (8) | −0.0014 (8) |
| C15 | 0.0367 (10) | 0.0413 (11) | 0.0286 (9) | 0.0010 (9) | 0.0197 (8) | 0.0039 (8) |
| C16 | 0.0267 (9) | 0.0343 (11) | 0.0331 (9) | −0.0029 (8) | 0.0168 (8) | −0.0006 (8) |
| C21 | 0.0251 (9) | 0.0294 (10) | 0.0252 (8) | 0.0009 (7) | 0.0108 (7) | −0.0002 (7) |
| C22 | 0.0244 (9) | 0.0328 (10) | 0.0273 (9) | −0.0019 (8) | 0.0113 (7) | −0.0035 (7) |
| C23 | 0.0247 (9) | 0.0423 (12) | 0.0329 (9) | 0.0027 (8) | 0.0080 (8) | −0.0035 (8) |
| C24 | 0.0338 (10) | 0.0401 (11) | 0.0276 (9) | 0.0002 (9) | 0.0043 (8) | 0.0007 (8) |
| C25 | 0.0441 (11) | 0.0454 (12) | 0.0243 (9) | 0.0004 (9) | 0.0131 (9) | −0.0043 (8) |
| C26 | 0.0366 (10) | 0.0402 (11) | 0.0294 (9) | 0.0046 (9) | 0.0167 (8) | −0.0024 (8) |
| C31 | 0.0240 (9) | 0.0300 (10) | 0.0271 (8) | −0.0024 (7) | 0.0117 (7) | −0.0002 (7) |
| C32 | 0.0245 (9) | 0.0335 (10) | 0.0309 (9) | −0.0004 (8) | 0.0127 (8) | 0.0041 (8) |
| C33 | 0.0325 (10) | 0.0434 (12) | 0.0395 (10) | 0.0044 (9) | 0.0143 (9) | 0.0137 (9) |
| C34 | 0.0461 (12) | 0.0509 (13) | 0.0350 (10) | −0.0047 (10) | 0.0214 (9) | 0.0104 (9) |
| C35 | 0.0397 (11) | 0.0485 (13) | 0.0373 (10) | −0.0071 (9) | 0.0253 (9) | −0.0013 (9) |
| C36 | 0.0278 (9) | 0.0378 (11) | 0.0340 (9) | −0.0005 (8) | 0.0152 (8) | −0.0010 (8) |
| O1—C1 | 1.2063 (18) | C15—H15A | 0.9300 |
| O2—C2 | 1.2050 (18) | C16—H16A | 0.9300 |
| O3—C3 | 1.2083 (18) | C21—C26 | 1.377 (2) |
| O4—C4 | 1.2101 (18) | C21—C22 | 1.384 (2) |
| N1—C1 | 1.4110 (19) | C22—C23 | 1.380 (2) |
| N1—C2 | 1.412 (2) | C23—C24 | 1.386 (2) |
| N1—C11 | 1.4320 (18) | C23—H23A | 0.9300 |
| N2—C4 | 1.400 (2) | C24—C25 | 1.383 (2) |
| N2—C3 | 1.4131 (19) | C24—H24A | 0.9300 |
| N2—C12 | 1.4328 (19) | C25—C26 | 1.393 (2) |
| C1—C21 | 1.485 (2) | C25—H25A | 0.9300 |
| C2—C22 | 1.484 (2) | C26—H26A | 0.9300 |
| C3—C31 | 1.480 (2) | C31—C32 | 1.382 (2) |
| C4—C32 | 1.484 (2) | C31—C36 | 1.383 (2) |
| C11—C16 | 1.385 (2) | C32—C33 | 1.381 (2) |
| C11—C12 | 1.388 (2) | C33—C34 | 1.388 (2) |
| C12—C13 | 1.386 (2) | C33—H33A | 0.9300 |
| C13—C14 | 1.380 (2) | C34—C35 | 1.383 (2) |
| C13—H13A | 0.9300 | C34—H34A | 0.9300 |
| C14—C15 | 1.378 (2) | C35—C36 | 1.387 (2) |
| C14—H14A | 0.9300 | C35—H35A | 0.9300 |
| C15—C16 | 1.383 (2) | C36—H36A | 0.9300 |
| C1—N1—C2 | 111.16 (13) | C26—C21—C22 | 121.72 (15) |
| C1—N1—C11 | 125.16 (13) | C26—C21—C1 | 129.55 (15) |
| C2—N1—C11 | 123.21 (12) | C22—C21—C1 | 108.68 (13) |
| C4—N2—C3 | 111.54 (12) | C23—C22—C21 | 121.09 (15) |
| C4—N2—C12 | 125.22 (12) | C23—C22—C2 | 130.42 (15) |
| C3—N2—C12 | 122.86 (13) | C21—C22—C2 | 108.45 (14) |
| O1—C1—N1 | 125.04 (14) | C22—C23—C24 | 117.67 (16) |
| O1—C1—C21 | 129.19 (15) | C22—C23—H23A | 121.2 |
| N1—C1—C21 | 105.77 (13) | C24—C23—H23A | 121.2 |
| O2—C2—N1 | 124.91 (15) | C25—C24—C23 | 121.19 (16) |
| O2—C2—C22 | 129.15 (15) | C25—C24—H24A | 119.4 |
| N1—C2—C22 | 105.93 (13) | C23—C24—H24A | 119.4 |
| O3—C3—N2 | 124.90 (14) | C24—C25—C26 | 121.09 (16) |
| O3—C3—C31 | 129.57 (14) | C24—C25—H25A | 119.5 |
| N2—C3—C31 | 105.53 (13) | C26—C25—H25A | 119.5 |
| O4—C4—N2 | 124.59 (15) | C21—C26—C25 | 117.24 (16) |
| O4—C4—C32 | 129.63 (15) | C21—C26—H26A | 121.4 |
| N2—C4—C32 | 105.77 (13) | C25—C26—H26A | 121.4 |
| C16—C11—C12 | 119.44 (14) | C32—C31—C36 | 121.38 (15) |
| C16—C11—N1 | 119.27 (14) | C32—C31—C3 | 108.62 (13) |
| C12—C11—N1 | 121.28 (13) | C36—C31—C3 | 130.00 (15) |
| C13—C12—C11 | 119.99 (14) | C33—C32—C31 | 121.41 (15) |
| C13—C12—N2 | 119.17 (14) | C33—C32—C4 | 130.07 (15) |
| C11—C12—N2 | 120.81 (13) | C31—C32—C4 | 108.52 (14) |
| C14—C13—C12 | 120.17 (15) | C32—C33—C34 | 117.47 (16) |
| C14—C13—H13A | 119.9 | C32—C33—H33A | 121.3 |
| C12—C13—H13A | 119.9 | C34—C33—H33A | 121.3 |
| C15—C14—C13 | 119.96 (15) | C35—C34—C33 | 121.09 (16) |
| C15—C14—H14A | 120.0 | C35—C34—H34A | 119.5 |
| C13—C14—H14A | 120.0 | C33—C34—H34A | 119.5 |
| C14—C15—C16 | 120.11 (15) | C34—C35—C36 | 121.35 (16) |
| C14—C15—H15A | 119.9 | C34—C35—H35A | 119.3 |
| C16—C15—H15A | 119.9 | C36—C35—H35A | 119.3 |
| C15—C16—C11 | 120.33 (15) | C31—C36—C35 | 117.31 (16) |
| C15—C16—H16A | 119.8 | C31—C36—H36A | 121.3 |
| C11—C16—H16A | 119.8 | C35—C36—H36A | 121.3 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C13—H13A···O4i | 0.93 | 2.39 | 3.321 (2) | 179 |
| C24—H24A···O3ii | 0.93 | 2.51 | 3.405 (2) | 161 |
| C26—H26A···O1iii | 0.93 | 2.53 | 3.434 (2) | 164 |
| C34—H34A···O2iv | 0.93 | 2.48 | 3.410 (2) | 177 |
| C36—H36A···O2v | 0.93 | 2.55 | 3.255 (2) | 133 |
| Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1, y, z−1; (iii) −x+1, −y, −z; (iv) x+1/2, −y+1/2, z−1/2; (v) x+1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C13—H13A···O4i | 0.93 | 2.39 | 3.321 (2) | 179 |
| C24—H24A···O3ii | 0.93 | 2.51 | 3.405 (2) | 161 |
| C26—H26A···O1iii | 0.93 | 2.53 | 3.434 (2) | 164 |
| C34—H34A···O2iv | 0.93 | 2.48 | 3.410 (2) | 177 |
| C36—H36A···O2v | 0.93 | 2.55 | 3.255 (2) | 133 |
| Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1, y, z−1; (iii) −x+1, −y, −z; (iv) x+1/2, −y+1/2, z−1/2; (v) x+1, y, z. |
This work was supported by the Postdoctoral Science Foundation, China (grant No. 2005038561)
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Isoindolinones and their derivatives have been investigated widely due to their profound 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 this paper, we report the crystal structure of the title compound.
As shown in Fig. 1, the structure determination indicates that the molecule is non-centrosymmetric. Due to steric encumbering, two isoindolinyl moieties are twisted to the benzene ring with dihedral angles of 58.15 (7) and 61.32 (7)°, respectively, similar to 62.31 (6)° found in 2-(2-pyridyl)isoindoline-1,3-dione (Liang & Li, 2007). The dihedral angle between the two isoindolinyl moieties is 39.45 (6)°. The molecules are linked together by weak C—H···O hydrogen bonding (Table 1).