Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031698/wk2067sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031698/wk2067Isup2.hkl |
CCDC reference: 657703
A solution of phthaloyl dichoride (420, 2 mmol) was added slowly over a period of 10 min to a solution of 4-(4-aminobenzyl)benzenamine (240 mg, 2 mmol) in dichloromethane (20 ml) at 273 K with light yellow solid precipitated. Triethylamine (5 ml) was then added, while the pecipitated light yellow solid was dissolved. After being stirred for 10 hr,the reacted solution became yellow suspension.The compound was purified by filtration with suction and dried (I) (yield 410 mg, 29.14%). Single crystals of (I) were obtained by recrystallization from DMF at room temperature.
All H atoms were initially located in a difference Fourier map and then included with constrained bond lengths and isotropic displacement parameters: C—H=0.93Å and Uiso(H)=1.5Ueq(C) for methyl, C—H=0.97Å and Uiso(H)=1.2Ueq(C) for methylene.
Bisimides are heterocyclic compounds, of which some have biological activivity. Moreover, they are synthetic precursor with application in organic synthesis, supramolecular chemistry, polymer synthesis, and for the development new materials and molecular electronic devices (Guzmán-Lucero et al., 2006).
The molecule of the title, (I) is shown in Fig. 1. The compound crystallizes with one half-molecule in the asymmetric unit, the other half being generated by a crystallographic twofold rotation axis passing through the central C atom. There are no signicant different between the bonds and angles of the two molecules. The dihedral angle between the planes of the two central benzene rings is 67.7 (4)°. The terminal isoindole group is approximately planar and makes adihedral angle of 39.20 (17)° with the attached benzene ring.
Intermolecular C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).
For related literature, see: Diego et al. (2006); James (1988).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids (arbitrary spheres for H atoms). |
C29H18N2O4 | F(000) = 476 |
Mr = 458.45 | Dx = 1.394 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 1420 reflections |
a = 31.669 (6) Å | θ = 2.6–23.9° |
b = 4.913 (1) Å | µ = 0.09 mm−1 |
c = 7.1543 (14) Å | T = 292 K |
β = 101.087 (3)° | Plate, colorless |
V = 1092.4 (4) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 2 |
Bruker SMART 4K CCD area-detector diffractometer | 1161 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.099 |
Graphite monochromator | θmax = 27.7°, θmin = 1.3° |
φ and ω scans | h = −38→40 |
4646 measured reflections | k = −6→6 |
1414 independent reflections | l = −9→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0709P)2 + 0.0873P] where P = (Fo2 + 2Fc2)/3 |
1414 reflections | (Δ/σ)max = 0.002 |
159 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
C29H18N2O4 | V = 1092.4 (4) Å3 |
Mr = 458.45 | Z = 2 |
Monoclinic, C2 | Mo Kα radiation |
a = 31.669 (6) Å | µ = 0.09 mm−1 |
b = 4.913 (1) Å | T = 292 K |
c = 7.1543 (14) Å | 0.30 × 0.20 × 0.20 mm |
β = 101.087 (3)° |
Bruker SMART 4K CCD area-detector diffractometer | 1161 reflections with I > 2σ(I) |
4646 measured reflections | Rint = 0.099 |
1414 independent reflections |
R[F2 > 2σ(F2)] = 0.050 | 1 restraint |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.20 e Å−3 |
1414 reflections | Δρmin = −0.20 e Å−3 |
159 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 | Occ. (<1) | |
C1 | 0.0000 | 1.2197 (11) | 0.5000 | 0.0462 (11) | |
H1A | 0.0149 | 1.3359 | 0.4244 | 0.055* | 0.50 |
H1B | −0.0149 | 1.3359 | 0.5756 | 0.055* | 0.50 |
O1 | 0.08076 (7) | 0.4639 (6) | 1.2283 (3) | 0.0545 (6) | |
N1 | 0.12141 (7) | 0.5510 (6) | 0.9965 (3) | 0.0411 (6) | |
C2 | 0.03274 (8) | 1.0474 (6) | 0.6323 (4) | 0.0380 (7) | |
C6 | 0.08665 (9) | 0.6935 (7) | 0.6772 (4) | 0.0430 (8) | |
H6 | 0.1027 | 0.5654 | 0.6253 | 0.052* | |
C7 | 0.09194 (9) | 0.7230 (7) | 0.8729 (4) | 0.0382 (7) | |
C5 | 0.06775 (10) | 0.9128 (7) | 0.9478 (4) | 0.0453 (8) | |
H5 | 0.0711 | 0.9328 | 1.0791 | 0.054* | |
C8 | 0.11301 (9) | 0.4301 (7) | 1.1647 (4) | 0.0411 (7) | |
C3 | 0.03847 (10) | 1.0736 (7) | 0.8271 (4) | 0.0462 (8) | |
H3 | 0.0224 | 1.2017 | 0.8788 | 0.055* | |
C4 | 0.05731 (9) | 0.8558 (7) | 0.5600 (4) | 0.0433 (7) | |
H4 | 0.0540 | 0.8359 | 0.4287 | 0.052* | |
C10 | 0.15041 (9) | 0.2547 (7) | 1.2393 (4) | 0.0436 (7) | |
C9 | 0.16170 (9) | 0.4632 (8) | 0.9611 (4) | 0.0467 (8) | |
C15 | 0.17918 (9) | 0.2712 (7) | 1.1170 (4) | 0.0452 (8) | |
O2 | 0.17754 (7) | 0.5373 (7) | 0.8300 (4) | 0.0663 (8) | |
C13 | 0.22405 (11) | −0.0462 (9) | 1.3047 (5) | 0.0626 (10) | |
H13 | 0.2492 | −0.1487 | 1.3296 | 0.075* | |
C12 | 0.19526 (12) | −0.0669 (10) | 1.4255 (5) | 0.0623 (10) | |
H12 | 0.2009 | −0.1861 | 1.5283 | 0.075* | |
C11 | 0.15807 (11) | 0.0869 (8) | 1.3963 (5) | 0.0538 (9) | |
H11 | 0.1389 | 0.0775 | 1.4796 | 0.065* | |
C14 | 0.21666 (10) | 0.1221 (8) | 1.1479 (5) | 0.0550 (9) | |
H14 | 0.2362 | 0.1344 | 1.0663 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.045 (2) | 0.043 (2) | 0.049 (2) | 0.000 | 0.0044 (19) | 0.000 |
O1 | 0.0553 (12) | 0.0652 (16) | 0.0487 (12) | 0.0067 (13) | 0.0246 (10) | −0.0001 (12) |
N1 | 0.0334 (12) | 0.0523 (16) | 0.0379 (12) | −0.0001 (12) | 0.0081 (9) | −0.0005 (12) |
C2 | 0.0318 (13) | 0.0395 (16) | 0.0429 (15) | −0.0057 (13) | 0.0075 (11) | −0.0021 (13) |
C6 | 0.0377 (15) | 0.051 (2) | 0.0422 (16) | 0.0029 (15) | 0.0117 (12) | −0.0059 (15) |
C7 | 0.0334 (14) | 0.0439 (16) | 0.0377 (14) | −0.0041 (13) | 0.0080 (11) | 0.0002 (14) |
C5 | 0.0512 (17) | 0.049 (2) | 0.0368 (15) | 0.0000 (16) | 0.0102 (12) | −0.0059 (14) |
C8 | 0.0449 (16) | 0.0454 (18) | 0.0343 (14) | −0.0037 (15) | 0.0111 (11) | −0.0040 (13) |
C3 | 0.0482 (17) | 0.0474 (19) | 0.0450 (16) | 0.0025 (15) | 0.0136 (13) | −0.0088 (15) |
C4 | 0.0424 (16) | 0.0526 (19) | 0.0354 (14) | 0.0019 (14) | 0.0085 (12) | −0.0031 (14) |
C10 | 0.0378 (15) | 0.0486 (18) | 0.0425 (16) | −0.0036 (14) | 0.0028 (12) | −0.0029 (14) |
C9 | 0.0327 (14) | 0.060 (2) | 0.0476 (17) | −0.0019 (15) | 0.0086 (12) | 0.0007 (16) |
C15 | 0.0368 (15) | 0.050 (2) | 0.0469 (17) | −0.0035 (14) | 0.0040 (13) | −0.0003 (15) |
O2 | 0.0431 (12) | 0.099 (2) | 0.0623 (14) | 0.0104 (14) | 0.0237 (11) | 0.0237 (15) |
C13 | 0.0462 (18) | 0.065 (2) | 0.072 (2) | 0.0046 (19) | −0.0004 (17) | 0.008 (2) |
C12 | 0.061 (2) | 0.061 (2) | 0.058 (2) | −0.001 (2) | −0.0065 (17) | 0.0114 (19) |
C11 | 0.0558 (19) | 0.062 (2) | 0.0417 (17) | −0.0080 (17) | 0.0043 (14) | 0.0063 (17) |
C14 | 0.0412 (17) | 0.065 (2) | 0.058 (2) | 0.0027 (16) | 0.0072 (15) | 0.0041 (18) |
C1—C2 | 1.520 (4) | C8—C10 | 1.479 (4) |
C1—C2i | 1.520 (4) | C3—H3 | 0.9300 |
C1—H1A | 0.9700 | C4—H4 | 0.9300 |
C1—H1B | 0.9700 | C10—C11 | 1.376 (5) |
O1—C8 | 1.207 (3) | C10—C15 | 1.382 (5) |
N1—C8 | 1.412 (4) | C9—O2 | 1.202 (4) |
N1—C9 | 1.415 (4) | C9—C15 | 1.484 (5) |
N1—C7 | 1.432 (4) | C15—C14 | 1.376 (5) |
C2—C3 | 1.376 (4) | C13—C12 | 1.375 (6) |
C2—C4 | 1.384 (4) | C13—C14 | 1.377 (5) |
C6—C4 | 1.379 (4) | C13—H13 | 0.9300 |
C6—C7 | 1.385 (4) | C12—C11 | 1.381 (5) |
C6—H6 | 0.9300 | C12—H12 | 0.9300 |
C7—C5 | 1.379 (4) | C11—H11 | 0.9300 |
C5—C3 | 1.386 (4) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | ||
C2—C1—C2i | 112.3 (4) | C5—C3—H3 | 119.3 |
C2—C1—H1A | 109.1 | C6—C4—C2 | 121.9 (3) |
C2i—C1—H1A | 109.1 | C6—C4—H4 | 119.1 |
C2—C1—H1B | 109.1 | C2—C4—H4 | 119.1 |
C2i—C1—H1B | 109.1 | C11—C10—C15 | 121.2 (3) |
H1A—C1—H1B | 107.9 | C11—C10—C8 | 130.3 (3) |
C8—N1—C9 | 110.4 (3) | C15—C10—C8 | 108.5 (3) |
C8—N1—C7 | 124.6 (2) | O2—C9—N1 | 125.0 (3) |
C9—N1—C7 | 124.9 (3) | O2—C9—C15 | 128.9 (3) |
C3—C2—C4 | 117.9 (3) | N1—C9—C15 | 106.2 (3) |
C3—C2—C1 | 121.3 (3) | C14—C15—C10 | 121.3 (3) |
C4—C2—C1 | 120.8 (3) | C14—C15—C9 | 130.2 (3) |
C4—C6—C7 | 119.4 (3) | C10—C15—C9 | 108.5 (3) |
C4—C6—H6 | 120.3 | C12—C13—C14 | 121.8 (4) |
C7—C6—H6 | 120.3 | C12—C13—H13 | 119.1 |
C5—C7—C6 | 119.7 (3) | C14—C13—H13 | 119.1 |
C5—C7—N1 | 120.2 (3) | C13—C12—C11 | 120.9 (4) |
C6—C7—N1 | 120.0 (3) | C13—C12—H12 | 119.6 |
C7—C5—C3 | 119.9 (3) | C11—C12—H12 | 119.6 |
C7—C5—H5 | 120.1 | C10—C11—C12 | 117.6 (3) |
C3—C5—H5 | 120.1 | C10—C11—H11 | 121.2 |
O1—C8—N1 | 125.1 (3) | C12—C11—H11 | 121.2 |
O1—C8—C10 | 128.4 (3) | C15—C14—C13 | 117.2 (4) |
N1—C8—C10 | 106.5 (3) | C15—C14—H14 | 121.4 |
C2—C3—C5 | 121.3 (3) | C13—C14—H14 | 121.4 |
C2—C3—H3 | 119.3 | ||
C2i—C1—C2—C3 | −122.7 (3) | O1—C8—C10—C15 | 177.8 (3) |
C2i—C1—C2—C4 | 56.4 (2) | N1—C8—C10—C15 | −0.7 (3) |
C4—C6—C7—C5 | 0.3 (5) | C8—N1—C9—O2 | −178.4 (4) |
C4—C6—C7—N1 | 178.3 (3) | C7—N1—C9—O2 | 5.5 (5) |
C8—N1—C7—C5 | 40.3 (4) | C8—N1—C9—C15 | 0.9 (4) |
C9—N1—C7—C5 | −144.2 (3) | C7—N1—C9—C15 | −175.2 (3) |
C8—N1—C7—C6 | −137.7 (3) | C11—C10—C15—C14 | −0.4 (5) |
C9—N1—C7—C6 | 37.8 (4) | C8—C10—C15—C14 | −178.1 (3) |
C6—C7—C5—C3 | −0.3 (5) | C11—C10—C15—C9 | 179.0 (3) |
N1—C7—C5—C3 | −178.3 (3) | C8—C10—C15—C9 | 1.2 (4) |
C9—N1—C8—O1 | −178.7 (3) | O2—C9—C15—C14 | −2.8 (7) |
C7—N1—C8—O1 | −2.7 (5) | N1—C9—C15—C14 | 177.9 (3) |
C9—N1—C8—C10 | −0.1 (3) | O2—C9—C15—C10 | 178.0 (4) |
C7—N1—C8—C10 | 175.9 (3) | N1—C9—C15—C10 | −1.3 (4) |
C4—C2—C3—C5 | −0.3 (5) | C14—C13—C12—C11 | −1.6 (6) |
C1—C2—C3—C5 | 178.8 (3) | C15—C10—C11—C12 | −0.9 (5) |
C7—C5—C3—C2 | 0.3 (5) | C8—C10—C11—C12 | 176.3 (4) |
C7—C6—C4—C2 | −0.3 (5) | C13—C12—C11—C10 | 1.8 (6) |
C3—C2—C4—C6 | 0.3 (5) | C10—C15—C14—C13 | 0.6 (5) |
C1—C2—C4—C6 | −178.8 (3) | C9—C15—C14—C13 | −178.5 (3) |
O1—C8—C10—C11 | 0.4 (6) | C12—C13—C14—C15 | 0.4 (6) |
N1—C8—C10—C11 | −178.1 (3) |
Symmetry code: (i) −x, y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1ii | 0.93 | 2.57 | 3.251 (4) | 131 |
Symmetry code: (ii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C29H18N2O4 |
Mr | 458.45 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 292 |
a, b, c (Å) | 31.669 (6), 4.913 (1), 7.1543 (14) |
β (°) | 101.087 (3) |
V (Å3) | 1092.4 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4646, 1414, 1161 |
Rint | 0.099 |
(sin θ/λ)max (Å−1) | 0.655 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.136, 1.05 |
No. of reflections | 1414 |
No. of parameters | 159 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.20 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
C1—C2 | 1.520 (4) | N1—C9 | 1.415 (4) |
O1—C8 | 1.207 (3) | N1—C7 | 1.432 (4) |
N1—C8 | 1.412 (4) | C9—O2 | 1.202 (4) |
C8—N1—C9 | 110.4 (3) | O1—C8—N1 | 125.1 (3) |
C8—N1—C7 | 124.6 (2) | O1—C8—C10 | 128.4 (3) |
C9—N1—C7 | 124.9 (3) | O2—C9—N1 | 125.0 (3) |
C5—C7—N1 | 120.2 (3) | N1—C9—C15 | 106.2 (3) |
C2i—C1—C2—C3 | −122.7 (3) | C7—N1—C8—C10 | 175.9 (3) |
C2i—C1—C2—C4 | 56.4 (2) | O1—C8—C10—C11 | 0.4 (6) |
C9—N1—C7—C5 | −144.2 (3) | N1—C8—C10—C11 | −178.1 (3) |
C8—N1—C7—C6 | −137.7 (3) | O1—C8—C10—C15 | 177.8 (3) |
C9—N1—C8—O1 | −178.7 (3) | C8—N1—C9—C15 | 0.9 (4) |
C7—N1—C8—O1 | −2.7 (5) | C7—N1—C9—C15 | −175.2 (3) |
C9—N1—C8—C10 | −0.1 (3) | C8—C10—C15—C14 | −178.1 (3) |
Symmetry code: (i) −x, y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1ii | 0.93 | 2.57 | 3.251 (4) | 130.8 |
Symmetry code: (ii) x, y, z−1. |
Bisimides are heterocyclic compounds, of which some have biological activivity. Moreover, they are synthetic precursor with application in organic synthesis, supramolecular chemistry, polymer synthesis, and for the development new materials and molecular electronic devices (Guzmán-Lucero et al., 2006).
The molecule of the title, (I) is shown in Fig. 1. The compound crystallizes with one half-molecule in the asymmetric unit, the other half being generated by a crystallographic twofold rotation axis passing through the central C atom. There are no signicant different between the bonds and angles of the two molecules. The dihedral angle between the planes of the two central benzene rings is 67.7 (4)°. The terminal isoindole group is approximately planar and makes adihedral angle of 39.20 (17)° with the attached benzene ring.
Intermolecular C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).