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

Li, Y.; Wang, Z.

doi:10.1107/S1600536807068249

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o388

doi:10.1107/S1600536807068249

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

Yitao Li ^a ^* and Zhiguo Wang ^b

^aKey Laboratory of Pesticides and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and ^bSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: lytm1234@yahoo.com.cn

(Received 5 November 2007; accepted 22 December 2007; online 9 January 2008)

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 ); 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_r = 594.46
Orthorhombic, P c c a
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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.168
S = 1.05
2607 reflections
232 parameters
64 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) $[x, -y+2, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

For details of the biological activity and uses of bisimide 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 top

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.

Computing details top

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

Figures top

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

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

Crystal data top

C₃₁H₁₆F₆N₂O₄	F(000) = 1208
M_r = 594.46	D_x = 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 = 2.6–21.8°
b = 12.5340 (18) Å	µ = 0.13 mm⁻¹
c = 15.792 (2) Å	T = 292 K
V = 2644.2 (6) Å³	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	1864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.119
Graphite monochromator	θ_max = 26.0°, θ_min = 2.6°
ϕ and ω scans	h = −16→16
15610 measured reflections	k = −15→13
2607 independent reflections	l = −19→19

Refinement top

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0607P)² + 1.4164P] where P = (F_o² + 2F_c²)/3
2607 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.24 e Å⁻³
64 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₃₁H₁₆F₆N₂O₄	V = 2644.2 (6) Å³
M_r = 594.46	Z = 4
Orthorhombic, Pcca	Mo Kα radiation
a = 13.3588 (19) Å	µ = 0.13 mm⁻¹
b = 12.5340 (18) Å	T = 292 K
c = 15.792 (2) Å	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	1864 reflections with I > 2σ(I)
15610 measured reflections	R_int = 0.119
2607 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	64 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
2607 reflections	Δρ_min = −0.23 e Å⁻³
232 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1/2, −y+1, z.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₁H₁₆F₆N₂O₄
M_r	594.46
Crystal system, space group	Orthorhombic, Pcca
Temperature (K)	292
a, b, c (Å)	13.3588 (19), 12.5340 (18), 15.792 (2)
V (Å³)	2644.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15610, 2607, 1864
R_int	0.119
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.168, 1.05
No. of reflections	2607
No. of parameters	232
No. of restraints	64
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.93	2.42	3.199 (4)	141.2

Symmetry code: (i) x, −y+2, z+1/2.

Acknowledgements

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

References

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