N,N'-{[Bis(trifluoro-meth-yl)methyl-ene]di-p-phenyl-ene}diphthalimide.

The molecule of the title compound, C(31)H(16)F(6)N(2)O(4), consists of two phthalimide units linked by a [bis-(trifluoro-meth-yl)methyl-ene]di-p-phenyl-ene bridge, with the two halves of the mol-ecule 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. Inter-molecular C-H⋯O hydrogen bonds link neighboring mol-ecules 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 ▶); Degenhardt et al. (2002 ▶); Mallakpour & Kowsari (2004 ▶); Zhang et al. (1999 ▶); Langhals & Kirner (2000 ▶); Yakimov & Forrest (2002 ▶). For a related structure, see: Li et al. (2007 ▶).

Experimental

Crystal data

C31H16F6N2O4

M = 594.46

Orthorhombic,

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 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

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

C31H16F6N2O4	F000 = 1208
Mr = 594.46	Dx = 1.493 Mg m−3
Orthorhombic, Pcca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 2679 reflections
a = 13.3588 (19) Å	θ = 2.6–21.8º
b = 12.5340 (18) Å	µ = 0.13 mm−1
c = 15.792 (2) Å	T = 292 (2) K
V = 2644.2 (6) Å3	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Bruker SMART 4K CCD area-detector diffractometer	1864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.119
Monochromator: graphite	θmax = 26.0º
T = 292(2) K	θmin = 2.6º
φ and ω scans	h = −16→16
Absorption correction: none	k = −15→13
15610 measured reflections	l = −19→19
2607 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)] = 0.066	H-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 reflections	Δρmax = 0.24 e Å−3
232 parameters	Δρmin = −0.23 e Å−3
64 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.1413 (6)	0.5169 (6)	0.0925 (5)	0.061 (3)	0.59
F1	0.1409 (5)	0.5845 (3)	0.0233 (3)	0.110 (2)	0.59
F2	0.0992 (5)	0.4244 (3)	0.0577 (3)	0.115 (2)	0.59
F3	0.0585 (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
C2	0.2500	0.5000	0.1377 (3)	0.089 (2)
C3	0.2705 (3)	0.6000 (2)	0.1916 (2)	0.0590 (10)
C4	0.2369 (3)	0.7005 (3)	0.1690 (2)	0.0572 (10)
H4	0.1967	0.7089	0.1214	0.069*
C5	0.3309 (3)	0.5905 (3)	0.2625 (2)	0.0641 (11)
H5	0.3531	0.5233	0.2788	0.077*
C6	0.2630 (3)	0.7884 (2)	0.21707 (19)	0.0460 (8)
H6	0.2388	0.8554	0.2022	0.055*
C7	0.3592 (3)	0.6783 (3)	0.3097 (2)	0.0555 (9)
H7	0.4011	0.6706	0.3564	0.067*
C8	0.3240 (2)	0.7780 (2)	0.28632 (19)	0.0419 (7)
C9	0.3798 (2)	0.9679 (2)	0.29929 (19)	0.0414 (7)
C10	0.3466 (2)	0.8763 (3)	0.42443 (19)	0.0414 (7)
C11	0.3948 (2)	1.0421 (2)	0.37121 (19)	0.0404 (7)
C12	0.4248 (3)	1.1469 (3)	0.3716 (2)	0.0517 (9)
H12	0.4403	1.1826	0.3217	0.062*
C13	0.4310 (3)	1.1972 (3)	0.4497 (2)	0.0595 (10)
H13	0.4506	1.2683	0.4522	0.071*
C14	0.4084 (3)	1.1434 (3)	0.5240 (2)	0.0560 (10)
H14	0.4129	1.1791	0.5755	0.067*
C15	0.3795 (2)	1.0383 (3)	0.5228 (2)	0.0500 (9)
H15	0.3648	1.0021	0.5726	0.060*
C16	0.3731 (2)	0.9880 (2)	0.44536 (18)	0.0382 (7)
N1	0.35108 (19)	0.86997 (19)	0.33529 (15)	0.0405 (6)
O1	0.38753 (18)	0.98510 (18)	0.22441 (13)	0.0569 (7)
O3	0.32502 (19)	0.80458 (19)	0.47064 (14)	0.0570 (7)

	U11	U22	U33	U12	U13	U23
C1	0.104 (8)	0.039 (5)	0.040 (4)	0.000 (5)	−0.012 (5)	0.007 (4)
F1	0.228 (7)	0.043 (2)	0.060 (3)	−0.030 (4)	−0.054 (4)	0.018 (2)
F2	0.200 (6)	0.041 (2)	0.105 (4)	−0.026 (3)	−0.081 (5)	0.001 (2)
F3	0.091 (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)
C2	0.199 (8)	0.028 (3)	0.039 (3)	−0.018 (4)	0.000	0.000
C3	0.107 (3)	0.0301 (17)	0.0400 (19)	−0.0091 (18)	0.004 (2)	0.0000 (14)
C4	0.095 (3)	0.0373 (18)	0.0391 (18)	−0.0116 (18)	−0.0078 (19)	0.0001 (14)
C5	0.111 (3)	0.0280 (17)	0.053 (2)	0.0087 (18)	−0.003 (2)	0.0038 (15)
C6	0.071 (2)	0.0292 (15)	0.0377 (17)	−0.0012 (15)	−0.0008 (16)	0.0028 (13)
C7	0.076 (2)	0.0424 (19)	0.048 (2)	0.0042 (17)	−0.0049 (18)	0.0026 (16)
C8	0.0587 (19)	0.0338 (16)	0.0333 (16)	−0.0039 (14)	0.0052 (15)	−0.0013 (13)
C9	0.0523 (19)	0.0385 (17)	0.0333 (17)	−0.0040 (14)	0.0012 (14)	0.0000 (13)
C10	0.0429 (17)	0.0455 (19)	0.0358 (17)	0.0020 (14)	0.0023 (13)	0.0026 (15)
C11	0.0427 (16)	0.0434 (18)	0.0351 (17)	−0.0030 (13)	0.0015 (14)	−0.0020 (13)
C12	0.063 (2)	0.0432 (19)	0.049 (2)	−0.0073 (16)	0.0010 (17)	−0.0029 (16)
C13	0.062 (2)	0.049 (2)	0.068 (3)	−0.0036 (17)	−0.0006 (19)	−0.0192 (19)
C14	0.0503 (19)	0.068 (3)	0.049 (2)	0.0047 (17)	−0.0017 (16)	−0.0275 (18)
C15	0.0458 (18)	0.068 (2)	0.0362 (18)	0.0035 (16)	−0.0020 (15)	−0.0117 (16)
C16	0.0369 (16)	0.0454 (18)	0.0322 (15)	0.0037 (13)	−0.0015 (13)	−0.0020 (13)
N1	0.0558 (15)	0.0345 (14)	0.0313 (14)	−0.0033 (12)	−0.0005 (12)	−0.0015 (11)
O1	0.0885 (18)	0.0518 (14)	0.0305 (12)	−0.0178 (12)	0.0006 (12)	0.0018 (10)
O3	0.0754 (16)	0.0545 (15)	0.0411 (13)	−0.0073 (12)	0.0015 (12)	0.0129 (11)

C1—F1	1.382 (7)	C5—H5	0.9300
C1—F2	1.401 (8)	C6—C8	1.370 (4)
C1—F3	1.422 (8)	C6—H6	0.9300
C1—C2	1.632 (7)	C7—C8	1.386 (4)
C1'—F1'	1.329 (8)	C7—H7	0.9300
C1'—F2'	1.332 (7)	C8—N1	1.434 (4)
C1'—F3'	1.339 (8)	C9—O1	1.207 (4)
C1'—C2	1.423 (7)	C9—N1	1.406 (4)
C1'—C1'i	1.645 (18)	C9—C11	1.482 (4)
C1'—F1'i	1.815 (12)	C10—O3	1.194 (4)
F1'—F2'i	1.350 (11)	C10—N1	1.411 (4)
F1'—C1'i	1.815 (12)	C10—C16	1.481 (4)
F2'—F1'i	1.350 (11)	C11—C12	1.373 (4)
C2—C1'i	1.423 (7)	C11—C16	1.383 (4)
C2—C3	1.540 (4)	C12—C13	1.387 (5)
C2—C3i	1.540 (4)	C12—H12	0.9300
C2—C1i	1.632 (7)	C13—C14	1.386 (5)
C3—C4	1.384 (5)	C13—H13	0.9300
C3—C5	1.386 (5)	C14—C15	1.374 (5)
C4—C6	1.383 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.378 (4)
C5—C7	1.381 (5)	C15—H15	0.9300
F1—C1—F2	101.3 (5)	C6—C4—C3	120.1 (3)
F1—C1—F3	102.4 (6)	C6—C4—H4	119.9
F2—C1—F3	100.0 (6)	C3—C4—H4	119.9
F1—C1—C2	115.3 (6)	C7—C5—C3	121.8 (3)
F2—C1—C2	114.9 (5)	C7—C5—H5	119.1
F3—C1—C2	120.1 (6)	C3—C5—H5	119.1
F1'—C1'—F2'	110.6 (6)	C8—C6—C4	120.8 (3)
F1'—C1'—F3'	114.7 (8)	C8—C6—H6	119.6
F2'—C1'—F3'	110.6 (7)	C4—C6—H6	119.6
F1'—C1'—C2	113.0 (6)	C5—C7—C8	118.8 (3)
F2'—C1'—C2	109.2 (7)	C5—C7—H7	120.6
F3'—C1'—C2	98.1 (6)	C8—C7—H7	120.6
F1'—C1'—C1'i	74.4 (6)	C6—C8—C7	120.0 (3)
F2'—C1'—C1'i	89.3 (7)	C6—C8—N1	120.3 (3)
F3'—C1'—C1'i	151.2 (6)	C7—C8—N1	119.7 (3)
C2—C1'—C1'i	54.7 (4)	O1—C9—N1	125.2 (3)
F1'—C1'—F1'i	80.3 (6)	O1—C9—C11	128.9 (3)
F2'—C1'—F1'i	47.8 (5)	N1—C9—C11	105.9 (2)
F3'—C1'—F1'i	158.3 (7)	O3—C10—N1	125.3 (3)
C2—C1'—F1'i	89.4 (6)	O3—C10—C16	129.3 (3)
C1'i—C1'—F1'i	44.8 (4)	N1—C10—C16	105.4 (3)
C1'—F1'—F2'i	103.5 (6)	C12—C11—C16	121.7 (3)
C1'—F1'—C1'i	60.8 (6)	C12—C11—C9	130.1 (3)
F2'i—F1'—C1'i	47.0 (4)	C16—C11—C9	108.2 (3)
C1'—F2'—F1'i	85.2 (6)	C11—C12—C13	117.2 (3)
C1'—C2—C1'i	70.6 (8)	C11—C12—H12	121.4
C1'—C2—C3	119.1 (3)	C13—C12—H12	121.4
C1'i—C2—C3	114.6 (4)	C14—C13—C12	121.2 (3)
C1'—C2—C3i	114.6 (4)	C14—C13—H13	119.4
C1'i—C2—C3i	119.1 (3)	C12—C13—H13	119.4
C3—C2—C3i	112.9 (4)	C15—C14—C13	121.1 (3)
C1'—C2—C1i	99.4 (6)	C15—C14—H14	119.5
C1'i—C2—C1i	28.8 (4)	C13—C14—H14	119.5
C3—C2—C1i	100.9 (3)	C14—C15—C16	117.9 (3)
C3i—C2—C1i	107.1 (3)	C14—C15—H15	121.0
C1'—C2—C1	28.8 (4)	C16—C15—H15	121.0
C1'i—C2—C1	99.4 (6)	C15—C16—C11	120.9 (3)
C3—C2—C1	107.1 (3)	C15—C16—C10	130.1 (3)
C3i—C2—C1	100.9 (3)	C11—C16—C10	108.9 (3)
C1i—C2—C1	128.2 (7)	C9—N1—C10	111.5 (2)
C4—C3—C5	118.4 (3)	C9—N1—C8	123.5 (2)
C4—C3—C2	122.7 (3)	C10—N1—C8	124.9 (2)
C5—C3—C2	118.8 (3)
F2'—C1'—F1'—F2'i	−103.3 (7)	C1'—C2—C3—C4	−3.8 (6)
F3'—C1'—F1'—F2'i	130.7 (8)	C1'i—C2—C3—C4	76.8 (6)
C2—C1'—F1'—F2'i	19.4 (8)	C3i—C2—C3—C4	−142.5 (4)
C1'i—C1'—F1'—F2'i	−20.2 (6)	C1i—C2—C3—C4	103.5 (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'i	150.9 (8)	C1'i—C2—C3—C5	−98.6 (6)
C2—C1'—F1'—C1'i	39.6 (5)	C3i—C2—C3—C5	42.1 (3)
F1'i—C1'—F1'—C1'i	−45.6 (4)	C1i—C2—C3—C5	−71.9 (5)
F1'—C1'—F2'—F1'i	54.2 (8)	C1—C2—C3—C5	152.2 (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—C7	174.6 (3)
F2'—C1'—C2—C1'i	74.8 (7)	C3—C4—C6—C8	1.5 (5)
F3'—C1'—C2—C1'i	−170.0 (9)	C3—C5—C7—C8	1.5 (6)
F1'i—C1'—C2—C1'i	30.4 (3)	C4—C6—C8—C7	−0.9 (5)
F1'—C1'—C2—C3	59.2 (8)	C4—C6—C8—N1	179.5 (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—N1	179.0 (3)
C1'i—C1'—C2—C3	108.0 (5)	O1—C9—C11—C12	−3.0 (6)
F1'i—C1'—C2—C3	138.4 (4)	N1—C9—C11—C12	178.6 (3)
F1'—C1'—C2—C3i	−162.7 (5)	O1—C9—C11—C16	177.2 (3)
F2'—C1'—C2—C3i	−39.1 (8)	N1—C9—C11—C16	−1.2 (3)
F3'—C1'—C2—C3i	76.1 (7)	C16—C11—C12—C13	−1.0 (5)
C1'i—C1'—C2—C3i	−114.0 (5)	C9—C11—C12—C13	179.2 (3)
F1'i—C1'—C2—C3i	−83.5 (5)	C11—C12—C13—C14	0.5 (5)
F1'—C1'—C2—C1i	−48.9 (7)	C12—C13—C14—C15	0.2 (5)
F2'—C1'—C2—C1i	74.7 (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—C10	178.5 (3)
F1'i—C1'—C2—C1i	30.3 (5)	C12—C11—C16—C15	0.9 (5)
F1'—C1'—C2—C1	130.9 (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—C1	9.7 (8)	C9—C11—C16—C10	1.8 (3)
C1'i—C1'—C2—C1	179.7 (12)	O3—C10—C16—C15	−0.3 (6)
F1'i—C1'—C2—C1	−149.9 (11)	N1—C10—C16—C15	179.4 (3)
F1—C1—C2—C1'	−42.3 (8)	O3—C10—C16—C11	178.6 (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—C10	0.0 (3)
F2—C1—C2—C1'i	75.3 (7)	O1—C9—N1—C8	−2.0 (5)
F3—C1—C2—C1'i	−165.4 (6)	C11—C9—N1—C8	176.4 (3)
F1—C1—C2—C3	77.5 (7)	O3—C10—N1—C9	−179.3 (3)
F2—C1—C2—C3	−165.2 (5)	C16—C10—N1—C9	1.0 (3)
F3—C1—C2—C3	−45.9 (7)	O3—C10—N1—C8	4.4 (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—C3i	72.4 (6)	C7—C8—N1—C9	136.9 (3)
F1—C1—C2—C1i	−42.1 (5)	C6—C8—N1—C10	132.3 (3)
F2—C1—C2—C1i	75.2 (6)	C7—C8—N1—C10	−47.2 (4)
F3—C1—C2—C1i	−165.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ii	0.93	2.42	3.199 (4)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.93	2.42	3.199 (4)	141

Symmetry code: (i) .