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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o388.
Published online 2008 January 9. doi:  10.1107/S1600536807068249
PMCID: PMC2960178

N,N′-{[Bis(trifluoro­meth­yl)methyl­ene]di-p-phenyl­ene}diphthalimide

Abstract

The molecule of the title compound, C31H16F6N2O4, consists of two phthalimide units linked by a [bis­(trifluoro­meth­yl)methyl­ene]di-p-phenyl­ene bridge, with the two halves of the mol­ecule related to each other by a twofold rotation axis. The dihedral angle between the planes of the two central benzene rings is 70.5 (3)°. The terminal isoindole groups are approximately planar, with a maximum r.m.s. deviation of 0.006 Å from the mean plane, and they form dihedral angles of 46.03 (3)° to the attached benzene rings. Inter­molecular C—H(...)O hydrogen bonds link neighboring mol­ecules into chains along the c axis.

Related literature

For details of the biological activity and uses of bis(­imide) derivatives, see: Rich et al. (1975 [triangle]); Degenhardt et al. (2002 [triangle]); Mallakpour & Kowsari (2004 [triangle]); Zhang et al. (1999 [triangle]); Langhals & Kirner (2000 [triangle]); Yakimov & Forrest (2002 [triangle]). For a related structure, see: Li et al. (2007 [triangle]).

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Object name is e-64-0o388-scheme1.jpg

Experimental

Crystal data

  • C31H16F6N2O4
  • M r = 594.46
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o388-efi1.jpg
  • a = 13.3588 (19) Å
  • b = 12.5340 (18) Å
  • c = 15.792 (2) Å
  • V = 2644.2 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 292 (2) K
  • 0.30 × 0.30 × 0.20 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: none
  • 15610 measured reflections
  • 2607 independent reflections
  • 1864 reflections with I > 2σ(I)
  • R int = 0.119

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.168
  • S = 1.05
  • 2607 reflections
  • 232 parameters
  • 64 restraints
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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: SHELXTL (Bruker, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068249/ez2112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068249/ez2112Isup2.hkl

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

Acknowledgments

The authors thank Dr Xiang-Gao Meng for the X-ray data collection.

supplementary crystallographic information

Comment

Bisimides are heterocyclic compounds that sometimes exhibit biological activity (Rich et al., 1975). Moreover, they are synthetic precursors with applications in organic synthesis (Degenhardt et al., 2002), polymer synthesis (Mallakpour & Kowsari, 2004), supramolecular chemistry (Zhang et al., 1999), and for the development of new materials (Langhals & Kirner, 2000) and molecular electronic devices (Yakimov & Forrest, 2002).

Following our studies on the synthesis of bisimides derivatives (Li et al., 2007), we report here the structure of the title compound (I), Fig. 1. In the molecule, two phthalimide units are linked by a (1,1-di-trifluoromethyl)-methylenedi-p-phenylene bridge. The dihedral angle between the planes of the two central benzene rings is 70.5 (3)°. The terminal isoindole group is approximately planar with a maximum r.m.s. deviation of 0.006Å from the best fit plane by C11 and makes a dihedral angle of 46.03 (3)° to the attached central benzene ring. Intermolecular C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).

Experimental

A solution of phthaloyl dichoride (420 mg, 2 mmol) was added slowly over a period of 10 min to a solution of 4-(2-(4-aminophenyl)-1,1,1,3,3,3- hexafluoropropan-2-yl)benzenamine (334 mg, 1 mmol) in dichloromethane (25 ml) at 273 K to yield a light yellow precipitate. Triethylamine (5 ml) was then added to dissolve the precipitate which became a yellow suspension after stirring for 12 h. The compound was filtered and dried to give (I), (yield 362 mg, 61%). Single crystals of (I) were obtained by recrystallization from DMF at room temperature.

Refinement

Non-hydrogen atoms were refined with anisotropic displacement parameters. One of the trifluoromethyl groups (C1/F1/F2/F3) of the title compound was found to be disordered over two orientations. The occupancies of the disordered positions C1/C1', F1/F1', F2/F2'and F3/F3' were refined to 0.59 (5) /0.41 (5). 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)=1.2Ueq(C) for aromatic H atoms.

Figures

Fig. 1.
The molecular structure of (I) showing atom labels with 50% probability displacement ellipsoids.

Crystal data

C31H16F6N2O4F000 = 1208
Mr = 594.46Dx = 1.493 Mg m3
Orthorhombic, PccaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2a 2acCell parameters from 2679 reflections
a = 13.3588 (19) Åθ = 2.6–21.8º
b = 12.5340 (18) ŵ = 0.13 mm1
c = 15.792 (2) ÅT = 292 (2) K
V = 2644.2 (6) Å3Block, colorless
Z = 40.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer1864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.119
Monochromator: graphiteθmax = 26.0º
T = 292(2) Kθmin = 2.6º
[var phi] and ω scansh = −16→16
Absorption correction: nonek = −15→13
15610 measured reflectionsl = −19→19
2607 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.168  w = 1/[σ2(Fo2) + (0.0607P)2 + 1.4164P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2607 reflectionsΔρmax = 0.24 e Å3
232 parametersΔρmin = −0.23 e Å3
64 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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*/UeqOcc. (<1)
C10.1413 (6)0.5169 (6)0.0925 (5)0.061 (3)0.59
F10.1409 (5)0.5845 (3)0.0233 (3)0.110 (2)0.59
F20.0992 (5)0.4244 (3)0.0577 (3)0.115 (2)0.59
F30.0585 (4)0.5547 (4)0.1406 (4)0.0905 (18)0.59
C1'0.1891 (7)0.5093 (6)0.0641 (4)0.067 (3)0.41
F1'0.2253 (6)0.5779 (5)0.0078 (4)0.088 (2)0.41
F2'0.1774 (6)0.4132 (4)0.0295 (4)0.083 (2)0.41
F3'0.1045 (5)0.5408 (7)0.1022 (6)0.072 (3)0.41
C20.25000.50000.1377 (3)0.089 (2)
C30.2705 (3)0.6000 (2)0.1916 (2)0.0590 (10)
C40.2369 (3)0.7005 (3)0.1690 (2)0.0572 (10)
H40.19670.70890.12140.069*
C50.3309 (3)0.5905 (3)0.2625 (2)0.0641 (11)
H50.35310.52330.27880.077*
C60.2630 (3)0.7884 (2)0.21707 (19)0.0460 (8)
H60.23880.85540.20220.055*
C70.3592 (3)0.6783 (3)0.3097 (2)0.0555 (9)
H70.40110.67060.35640.067*
C80.3240 (2)0.7780 (2)0.28632 (19)0.0419 (7)
C90.3798 (2)0.9679 (2)0.29929 (19)0.0414 (7)
C100.3466 (2)0.8763 (3)0.42443 (19)0.0414 (7)
C110.3948 (2)1.0421 (2)0.37121 (19)0.0404 (7)
C120.4248 (3)1.1469 (3)0.3716 (2)0.0517 (9)
H120.44031.18260.32170.062*
C130.4310 (3)1.1972 (3)0.4497 (2)0.0595 (10)
H130.45061.26830.45220.071*
C140.4084 (3)1.1434 (3)0.5240 (2)0.0560 (10)
H140.41291.17910.57550.067*
C150.3795 (2)1.0383 (3)0.5228 (2)0.0500 (9)
H150.36481.00210.57260.060*
C160.3731 (2)0.9880 (2)0.44536 (18)0.0382 (7)
N10.35108 (19)0.86997 (19)0.33529 (15)0.0405 (6)
O10.38753 (18)0.98510 (18)0.22441 (13)0.0569 (7)
O30.32502 (19)0.80458 (19)0.47064 (14)0.0570 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.104 (8)0.039 (5)0.040 (4)0.000 (5)−0.012 (5)0.007 (4)
F10.228 (7)0.043 (2)0.060 (3)−0.030 (4)−0.054 (4)0.018 (2)
F20.200 (6)0.041 (2)0.105 (4)−0.026 (3)−0.081 (5)0.001 (2)
F30.091 (4)0.067 (3)0.114 (5)−0.007 (3)−0.036 (3)0.013 (3)
C1'0.129 (8)0.038 (5)0.033 (5)−0.027 (6)0.005 (5)−0.008 (4)
F1'0.146 (6)0.055 (4)0.061 (4)−0.008 (5)−0.025 (5)0.007 (3)
F2'0.120 (5)0.053 (4)0.075 (5)−0.010 (4)−0.040 (4)−0.014 (3)
F3'0.046 (5)0.055 (5)0.115 (8)0.016 (4)−0.029 (4)−0.005 (5)
C20.199 (8)0.028 (3)0.039 (3)−0.018 (4)0.0000.000
C30.107 (3)0.0301 (17)0.0400 (19)−0.0091 (18)0.004 (2)0.0000 (14)
C40.095 (3)0.0373 (18)0.0391 (18)−0.0116 (18)−0.0078 (19)0.0001 (14)
C50.111 (3)0.0280 (17)0.053 (2)0.0087 (18)−0.003 (2)0.0038 (15)
C60.071 (2)0.0292 (15)0.0377 (17)−0.0012 (15)−0.0008 (16)0.0028 (13)
C70.076 (2)0.0424 (19)0.048 (2)0.0042 (17)−0.0049 (18)0.0026 (16)
C80.0587 (19)0.0338 (16)0.0333 (16)−0.0039 (14)0.0052 (15)−0.0013 (13)
C90.0523 (19)0.0385 (17)0.0333 (17)−0.0040 (14)0.0012 (14)0.0000 (13)
C100.0429 (17)0.0455 (19)0.0358 (17)0.0020 (14)0.0023 (13)0.0026 (15)
C110.0427 (16)0.0434 (18)0.0351 (17)−0.0030 (13)0.0015 (14)−0.0020 (13)
C120.063 (2)0.0432 (19)0.049 (2)−0.0073 (16)0.0010 (17)−0.0029 (16)
C130.062 (2)0.049 (2)0.068 (3)−0.0036 (17)−0.0006 (19)−0.0192 (19)
C140.0503 (19)0.068 (3)0.049 (2)0.0047 (17)−0.0017 (16)−0.0275 (18)
C150.0458 (18)0.068 (2)0.0362 (18)0.0035 (16)−0.0020 (15)−0.0117 (16)
C160.0369 (16)0.0454 (18)0.0322 (15)0.0037 (13)−0.0015 (13)−0.0020 (13)
N10.0558 (15)0.0345 (14)0.0313 (14)−0.0033 (12)−0.0005 (12)−0.0015 (11)
O10.0885 (18)0.0518 (14)0.0305 (12)−0.0178 (12)0.0006 (12)0.0018 (10)
O30.0754 (16)0.0545 (15)0.0411 (13)−0.0073 (12)0.0015 (12)0.0129 (11)

Geometric parameters (Å, °)

C1—F11.382 (7)C5—H50.9300
C1—F21.401 (8)C6—C81.370 (4)
C1—F31.422 (8)C6—H60.9300
C1—C21.632 (7)C7—C81.386 (4)
C1'—F1'1.329 (8)C7—H70.9300
C1'—F2'1.332 (7)C8—N11.434 (4)
C1'—F3'1.339 (8)C9—O11.207 (4)
C1'—C21.423 (7)C9—N11.406 (4)
C1'—C1'i1.645 (18)C9—C111.482 (4)
C1'—F1'i1.815 (12)C10—O31.194 (4)
F1'—F2'i1.350 (11)C10—N11.411 (4)
F1'—C1'i1.815 (12)C10—C161.481 (4)
F2'—F1'i1.350 (11)C11—C121.373 (4)
C2—C1'i1.423 (7)C11—C161.383 (4)
C2—C31.540 (4)C12—C131.387 (5)
C2—C3i1.540 (4)C12—H120.9300
C2—C1i1.632 (7)C13—C141.386 (5)
C3—C41.384 (5)C13—H130.9300
C3—C51.386 (5)C14—C151.374 (5)
C4—C61.383 (4)C14—H140.9300
C4—H40.9300C15—C161.378 (4)
C5—C71.381 (5)C15—H150.9300
F1—C1—F2101.3 (5)C6—C4—C3120.1 (3)
F1—C1—F3102.4 (6)C6—C4—H4119.9
F2—C1—F3100.0 (6)C3—C4—H4119.9
F1—C1—C2115.3 (6)C7—C5—C3121.8 (3)
F2—C1—C2114.9 (5)C7—C5—H5119.1
F3—C1—C2120.1 (6)C3—C5—H5119.1
F1'—C1'—F2'110.6 (6)C8—C6—C4120.8 (3)
F1'—C1'—F3'114.7 (8)C8—C6—H6119.6
F2'—C1'—F3'110.6 (7)C4—C6—H6119.6
F1'—C1'—C2113.0 (6)C5—C7—C8118.8 (3)
F2'—C1'—C2109.2 (7)C5—C7—H7120.6
F3'—C1'—C298.1 (6)C8—C7—H7120.6
F1'—C1'—C1'i74.4 (6)C6—C8—C7120.0 (3)
F2'—C1'—C1'i89.3 (7)C6—C8—N1120.3 (3)
F3'—C1'—C1'i151.2 (6)C7—C8—N1119.7 (3)
C2—C1'—C1'i54.7 (4)O1—C9—N1125.2 (3)
F1'—C1'—F1'i80.3 (6)O1—C9—C11128.9 (3)
F2'—C1'—F1'i47.8 (5)N1—C9—C11105.9 (2)
F3'—C1'—F1'i158.3 (7)O3—C10—N1125.3 (3)
C2—C1'—F1'i89.4 (6)O3—C10—C16129.3 (3)
C1'i—C1'—F1'i44.8 (4)N1—C10—C16105.4 (3)
C1'—F1'—F2'i103.5 (6)C12—C11—C16121.7 (3)
C1'—F1'—C1'i60.8 (6)C12—C11—C9130.1 (3)
F2'i—F1'—C1'i47.0 (4)C16—C11—C9108.2 (3)
C1'—F2'—F1'i85.2 (6)C11—C12—C13117.2 (3)
C1'—C2—C1'i70.6 (8)C11—C12—H12121.4
C1'—C2—C3119.1 (3)C13—C12—H12121.4
C1'i—C2—C3114.6 (4)C14—C13—C12121.2 (3)
C1'—C2—C3i114.6 (4)C14—C13—H13119.4
C1'i—C2—C3i119.1 (3)C12—C13—H13119.4
C3—C2—C3i112.9 (4)C15—C14—C13121.1 (3)
C1'—C2—C1i99.4 (6)C15—C14—H14119.5
C1'i—C2—C1i28.8 (4)C13—C14—H14119.5
C3—C2—C1i100.9 (3)C14—C15—C16117.9 (3)
C3i—C2—C1i107.1 (3)C14—C15—H15121.0
C1'—C2—C128.8 (4)C16—C15—H15121.0
C1'i—C2—C199.4 (6)C15—C16—C11120.9 (3)
C3—C2—C1107.1 (3)C15—C16—C10130.1 (3)
C3i—C2—C1100.9 (3)C11—C16—C10108.9 (3)
C1i—C2—C1128.2 (7)C9—N1—C10111.5 (2)
C4—C3—C5118.4 (3)C9—N1—C8123.5 (2)
C4—C3—C2122.7 (3)C10—N1—C8124.9 (2)
C5—C3—C2118.8 (3)
F2'—C1'—F1'—F2'i−103.3 (7)C1'—C2—C3—C4−3.8 (6)
F3'—C1'—F1'—F2'i130.7 (8)C1'i—C2—C3—C476.8 (6)
C2—C1'—F1'—F2'i19.4 (8)C3i—C2—C3—C4−142.5 (4)
C1'i—C1'—F1'—F2'i−20.2 (6)C1i—C2—C3—C4103.5 (5)
F1'i—C1'—F1'—F2'i−65.8 (7)C1—C2—C3—C4−32.4 (5)
F2'—C1'—F1'—C1'i−83.2 (8)C1'—C2—C3—C5−179.2 (5)
F3'—C1'—F1'—C1'i150.9 (8)C1'i—C2—C3—C5−98.6 (6)
C2—C1'—F1'—C1'i39.6 (5)C3i—C2—C3—C542.1 (3)
F1'i—C1'—F1'—C1'i−45.6 (4)C1i—C2—C3—C5−71.9 (5)
F1'—C1'—F2'—F1'i54.2 (8)C1—C2—C3—C5152.2 (4)
F3'—C1'—F2'—F1'i−177.6 (8)C5—C3—C4—C6−0.5 (6)
C2—C1'—F2'—F1'i−70.8 (7)C2—C3—C4—C6−175.9 (3)
C1'i—C1'—F2'—F1'i−18.8 (5)C4—C3—C5—C7−1.0 (6)
F1'—C1'—C2—C1'i−48.7 (5)C2—C3—C5—C7174.6 (3)
F2'—C1'—C2—C1'i74.8 (7)C3—C4—C6—C81.5 (5)
F3'—C1'—C2—C1'i−170.0 (9)C3—C5—C7—C81.5 (6)
F1'i—C1'—C2—C1'i30.4 (3)C4—C6—C8—C7−0.9 (5)
F1'—C1'—C2—C359.2 (8)C4—C6—C8—N1179.5 (3)
F2'—C1'—C2—C3−177.2 (5)C5—C7—C8—C6−0.5 (5)
F3'—C1'—C2—C3−62.0 (7)C5—C7—C8—N1179.0 (3)
C1'i—C1'—C2—C3108.0 (5)O1—C9—C11—C12−3.0 (6)
F1'i—C1'—C2—C3138.4 (4)N1—C9—C11—C12178.6 (3)
F1'—C1'—C2—C3i−162.7 (5)O1—C9—C11—C16177.2 (3)
F2'—C1'—C2—C3i−39.1 (8)N1—C9—C11—C16−1.2 (3)
F3'—C1'—C2—C3i76.1 (7)C16—C11—C12—C13−1.0 (5)
C1'i—C1'—C2—C3i−114.0 (5)C9—C11—C12—C13179.2 (3)
F1'i—C1'—C2—C3i−83.5 (5)C11—C12—C13—C140.5 (5)
F1'—C1'—C2—C1i−48.9 (7)C12—C13—C14—C150.2 (5)
F2'—C1'—C2—C1i74.7 (7)C13—C14—C15—C16−0.4 (5)
F3'—C1'—C2—C1i−170.1 (6)C14—C15—C16—C11−0.2 (5)
C1'i—C1'—C2—C1i−0.2 (6)C14—C15—C16—C10178.5 (3)
F1'i—C1'—C2—C1i30.3 (5)C12—C11—C16—C150.9 (5)
F1'—C1'—C2—C1130.9 (12)C9—C11—C16—C15−179.2 (3)
F2'—C1'—C2—C1−105.5 (12)C12—C11—C16—C10−178.0 (3)
F3'—C1'—C2—C19.7 (8)C9—C11—C16—C101.8 (3)
C1'i—C1'—C2—C1179.7 (12)O3—C10—C16—C15−0.3 (6)
F1'i—C1'—C2—C1−149.9 (11)N1—C10—C16—C15179.4 (3)
F1—C1—C2—C1'−42.3 (8)O3—C10—C16—C11178.6 (3)
F2—C1—C2—C1'75.0 (10)N1—C10—C16—C11−1.7 (3)
F3—C1—C2—C1'−165.7 (13)O1—C9—N1—C10−178.4 (3)
F1—C1—C2—C1'i−42.0 (7)C11—C9—N1—C100.0 (3)
F2—C1—C2—C1'i75.3 (7)O1—C9—N1—C8−2.0 (5)
F3—C1—C2—C1'i−165.4 (6)C11—C9—N1—C8176.4 (3)
F1—C1—C2—C377.5 (7)O3—C10—N1—C9−179.3 (3)
F2—C1—C2—C3−165.2 (5)C16—C10—N1—C91.0 (3)
F3—C1—C2—C3−45.9 (7)O3—C10—N1—C84.4 (5)
F1—C1—C2—C3i−164.3 (5)C16—C10—N1—C8−175.3 (3)
F2—C1—C2—C3i−47.0 (7)C6—C8—N1—C9−43.6 (4)
F3—C1—C2—C3i72.4 (6)C7—C8—N1—C9136.9 (3)
F1—C1—C2—C1i−42.1 (5)C6—C8—N1—C10132.3 (3)
F2—C1—C2—C1i75.2 (6)C7—C8—N1—C10−47.2 (4)
F3—C1—C2—C1i−165.5 (7)

Symmetry codes: (i) −x+1/2, −y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15···O1ii0.932.423.199 (4)141

Symmetry codes: (ii) x, −y+2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2112).

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