1,5-Bis(2,3,4,5-tetra­fluoro­benzo­yl)-1,5-diaza­cyclo­octa­ne

Dong, J.; Tian, L.-J.; Qu, Y.

doi:10.1107/S1600536807060242

1,5-Bis(2,3,4,5-tetrafluorobenzoyl)-1,5-diazacyclooctane

In the title compound, C₂₀H₁₄F₈N₂O₂, the eight-membered 1,5-diazacyclooctane ring adopts a boat-chair conformation. The dihedral angle between the benzene ring planes is 88.81 (11)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060242/hb2666sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060242/hb2666Isup2.hkl Contains datablock I

CCDC reference: 673046

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Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.146
Data-to-parameter ratio = 13.2

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No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.97
PLAT432_ALERT_2_C Short Inter X...Y Contact  C18    ..  C18     ..       3.18 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
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Comment top

1,5-Diazacyclooctane (DACO), the most typical example of diazamesocycles, offers unique conformational requirements and potential for further functionalization (Musker 1992). A number of derivatives of DACO have been prepared by substituting the hydrogen atom on the amine groups with functional pendant arms such as pyridine, imidazole, phenol, carboxylic acid and thioalcohol (Bu et al., 2001; Du & Bu, 2004; Grapperhaus & Darensbourg, 1998). Several strucures of the derivatives such as 1,5-bis(2-pyridylmethyl)-1,5-diazacyclooctane (Halfen et al., 2002), 1,4,8,11-tetra-azatricyclo(9.3.3.3^4,8)icosane (Watson et al., 2006) and 1,5-bis(1-methyl-2-imidazolylmethyl)-1,5-diazoniacyclooctane (Du et al., 2000) have been reported. We herein report the structure of title compound, (I), (Fig. 1).

The DACO ring in (I) adopts the normal boat/chair conformation, and the bond distances and angles are all in normal range (Du et al., 2001; Halfen et al., 2002) with the mean C–C and C–N distances being 1.507 (4) and 1.470 (3) Å, respectively, and the bond angles ranging from 114.27 (19) to 118.07 (18)°. The dihedral angles of two phenyl rings planes and two amide planes are 88.77 (7) and 37.86 (14)°, respectively. The C–O and C–N bond lengths of the amide are similar to those found in N,N'-bis(2,3,4,5-tetrafluorobenzoyl)piperazine [1.2275 (18) Å and 1.3409 (19) Å, respectively] (Zhang & Lu, 2007). The dihedral angle between the phenyl ring planes is 88.81 (11)°.

Related literature top

For related literature, see: Bu et al. (2001); Du & Bu (2004); Du et al. (2000, 2001); Grapperhaus & Darensbourg (1998); Halfen et al. (2002); Musker (1992); Watson et al. (2006); Zhang & Lu (2007).

Experimental top

The title compound was synthesized by the reaction of 2,3,4,5-tetrafluorobenzoyl chloride (2.12 g, 10 mmol) with 1,5-diazacyclooctane (0.57 g, 5 mmol) in the presence of triethylamine (1.01 g, 10 mmol) in ethanol solution (30 ml). Colourless blocks of (I) (yield 78%) were obtained by slow evaporation of an ethanol solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity.

1,5-Bis(2,3,4,5-tetrafluorobenzoyl)-1,5-diazacyclooctane top

Crystal data top

C₂₀H₁₄F₈N₂O₂	F(000) = 1888
M_r = 466.33	D_x = 1.602 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 7221 reflections
a = 14.8085 (11) Å	θ = 2.3–21.6°
b = 20.5518 (16) Å	µ = 0.16 mm⁻¹
c = 12.7062 (10) Å	T = 295 K
V = 3867.0 (5) Å³	Block, colourless
Z = 8	0.36 × 0.30 × 0.24 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3805 independent reflections
Radiation source: fine-focus sealed tube	2837 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −18→18
T_min = 0.942, T_max = 0.962	k = −25→25
27117 measured reflections	l = −15→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0719P)² + 1.346P] where P = (F_o² + 2F_c²)/3
3805 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₀H₁₄F₈N₂O₂	V = 3867.0 (5) Å³
M_r = 466.33	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 14.8085 (11) Å	µ = 0.16 mm⁻¹
b = 20.5518 (16) Å	T = 295 K
c = 12.7062 (10) Å	0.36 × 0.30 × 0.24 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3805 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2837 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.962	R_int = 0.026
27117 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.04	Δρ_max = 0.50 e Å⁻³
3805 reflections	Δρ_min = −0.17 e Å⁻³
289 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
F1	1.03822 (13)	0.40699 (9)	−0.15578 (13)	0.1034 (6)
F2	1.12461 (12)	0.50629 (8)	−0.06219 (14)	0.0970 (5)
F3	1.16418 (12)	0.49973 (7)	0.14554 (15)	0.0955 (5)
F4	1.11569 (13)	0.39500 (7)	0.25721 (11)	0.0916 (5)
F5	0.74987 (11)	0.08897 (8)	0.18853 (14)	0.0910 (5)
F6	0.81750 (14)	−0.03319 (8)	0.18206 (17)	0.1094 (6)
F7	0.99332 (15)	−0.05255 (8)	0.13222 (13)	0.1056 (6)
F8	1.10061 (12)	0.04879 (10)	0.08864 (14)	0.1003 (6)
N1	0.90720 (12)	0.29461 (9)	−0.09016 (14)	0.0599 (5)
N2	0.80349 (12)	0.22324 (9)	0.06928 (14)	0.0579 (5)
O1	1.03989 (12)	0.24206 (10)	−0.06866 (16)	0.0849 (6)
O2	0.87133 (16)	0.23209 (9)	0.22774 (15)	0.0912 (6)
C1	1.05645 (15)	0.40272 (13)	−0.05361 (18)	0.0650 (6)
C2	1.10072 (16)	0.45372 (12)	−0.0062 (2)	0.0663 (6)
C3	1.12042 (16)	0.45057 (11)	0.0988 (2)	0.0641 (6)
C4	1.09579 (16)	0.39645 (12)	0.15442 (18)	0.0619 (6)
C5	1.05293 (15)	0.34503 (11)	0.10727 (17)	0.0586 (5)
H5	1.0381	0.3083	0.1463	0.070*
C6	1.03189 (13)	0.34806 (11)	0.00162 (17)	0.0560 (5)
C7	0.99237 (15)	0.29038 (12)	−0.05516 (17)	0.0593 (5)
C8	0.87319 (18)	0.24394 (13)	−0.16115 (18)	0.0717 (7)
H8A	0.9187	0.2352	−0.2142	0.086*
H8B	0.8200	0.2604	−0.1970	0.086*
C9	0.84910 (18)	0.18079 (13)	−0.10705 (19)	0.0713 (7)
H9A	0.8286	0.1504	−0.1604	0.086*
H9B	0.9038	0.1629	−0.0766	0.086*
C10	0.77848 (16)	0.18371 (12)	−0.02210 (18)	0.0662 (6)
H10A	0.7233	0.2011	−0.0520	0.079*
H10B	0.7658	0.1398	0.0016	0.079*
C11	0.76174 (17)	0.28843 (13)	0.0803 (2)	0.0717 (6)
H11A	0.7957	0.3128	0.1324	0.086*
H11B	0.7009	0.2829	0.1072	0.086*
C12	0.75687 (16)	0.32815 (13)	−0.0184 (2)	0.0761 (7)
H12A	0.7219	0.3670	−0.0037	0.091*
H12B	0.7241	0.3033	−0.0709	0.091*
C13	0.84638 (16)	0.34870 (12)	−0.0655 (2)	0.0716 (7)
H13A	0.8348	0.3731	−0.1294	0.086*
H13B	0.8765	0.3777	−0.0165	0.086*
C14	0.85343 (15)	0.20073 (11)	0.14872 (17)	0.0603 (6)
C15	0.89052 (15)	0.13281 (11)	0.13940 (16)	0.0578 (5)
C16	0.83737 (17)	0.07971 (12)	0.16267 (18)	0.0659 (6)
C17	0.8707 (2)	0.01773 (13)	0.1597 (2)	0.0746 (7)
C18	0.9594 (2)	0.00780 (13)	0.13399 (18)	0.0746 (7)
C19	1.01321 (18)	0.06046 (14)	0.11227 (18)	0.0710 (7)
C20	0.98093 (16)	0.12265 (13)	0.11452 (17)	0.0642 (6)
H20	1.0187	0.1576	0.0997	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1175 (14)	0.1279 (14)	0.0649 (10)	−0.0298 (11)	−0.0231 (9)	0.0331 (9)
F2	0.1127 (12)	0.0797 (10)	0.0986 (12)	−0.0191 (9)	−0.0009 (10)	0.0303 (9)
F3	0.1125 (13)	0.0683 (9)	0.1057 (13)	−0.0139 (9)	−0.0222 (10)	−0.0067 (8)
F4	0.1335 (14)	0.0847 (10)	0.0566 (8)	−0.0044 (9)	−0.0140 (8)	−0.0050 (7)
F5	0.0745 (10)	0.0937 (11)	0.1049 (12)	−0.0148 (8)	0.0144 (9)	0.0077 (9)
F6	0.1366 (16)	0.0754 (10)	0.1161 (15)	−0.0261 (10)	0.0034 (12)	0.0104 (10)
F7	0.1576 (17)	0.0815 (11)	0.0776 (11)	0.0311 (11)	−0.0003 (11)	−0.0045 (8)
F8	0.0860 (11)	0.1299 (14)	0.0850 (11)	0.0268 (10)	0.0088 (9)	−0.0015 (10)
N1	0.0538 (10)	0.0715 (12)	0.0543 (10)	−0.0045 (9)	−0.0046 (8)	0.0054 (9)
N2	0.0504 (10)	0.0667 (11)	0.0565 (10)	−0.0085 (8)	−0.0036 (8)	−0.0016 (8)
O1	0.0597 (10)	0.0946 (13)	0.1006 (14)	0.0095 (9)	0.0001 (9)	−0.0280 (11)
O2	0.1234 (16)	0.0831 (12)	0.0671 (11)	0.0120 (11)	−0.0308 (11)	−0.0211 (9)
C1	0.0562 (13)	0.0834 (16)	0.0553 (13)	−0.0008 (12)	−0.0063 (10)	0.0120 (11)
C2	0.0580 (13)	0.0664 (14)	0.0745 (15)	−0.0007 (11)	0.0015 (11)	0.0173 (12)
C3	0.0620 (13)	0.0569 (13)	0.0734 (15)	0.0024 (11)	−0.0034 (11)	−0.0029 (11)
C4	0.0662 (14)	0.0673 (14)	0.0521 (12)	0.0100 (11)	−0.0016 (10)	−0.0026 (10)
C5	0.0603 (13)	0.0609 (13)	0.0545 (12)	0.0051 (10)	0.0076 (10)	0.0038 (10)
C6	0.0434 (10)	0.0687 (13)	0.0559 (12)	0.0029 (10)	0.0032 (9)	0.0040 (10)
C7	0.0500 (12)	0.0741 (14)	0.0537 (12)	0.0008 (11)	0.0052 (9)	−0.0008 (10)
C8	0.0716 (15)	0.0956 (18)	0.0480 (12)	−0.0049 (13)	−0.0106 (11)	−0.0005 (12)
C9	0.0801 (16)	0.0776 (16)	0.0562 (13)	−0.0080 (13)	−0.0150 (12)	−0.0166 (12)
C10	0.0620 (13)	0.0731 (14)	0.0636 (14)	−0.0156 (11)	−0.0180 (11)	−0.0012 (11)
C11	0.0558 (13)	0.0807 (16)	0.0784 (16)	0.0056 (12)	0.0011 (12)	−0.0039 (13)
C12	0.0549 (13)	0.0829 (16)	0.0905 (18)	0.0100 (12)	−0.0161 (13)	−0.0035 (14)
C13	0.0603 (14)	0.0677 (14)	0.0867 (17)	0.0053 (11)	−0.0142 (12)	0.0147 (13)
C14	0.0600 (13)	0.0688 (14)	0.0522 (12)	−0.0085 (11)	−0.0024 (10)	−0.0037 (10)
C15	0.0639 (13)	0.0669 (14)	0.0427 (10)	−0.0081 (11)	−0.0042 (9)	−0.0017 (9)
C16	0.0687 (15)	0.0749 (16)	0.0541 (13)	−0.0068 (12)	0.0009 (11)	−0.0015 (11)
C17	0.099 (2)	0.0675 (16)	0.0574 (14)	−0.0140 (14)	−0.0018 (14)	0.0004 (11)
C18	0.107 (2)	0.0706 (16)	0.0464 (13)	0.0142 (15)	−0.0052 (13)	−0.0056 (11)
C19	0.0711 (16)	0.0952 (19)	0.0466 (12)	0.0102 (14)	0.0014 (11)	−0.0032 (12)
C20	0.0678 (15)	0.0777 (15)	0.0472 (12)	−0.0041 (12)	−0.0031 (10)	0.0008 (10)

Geometric parameters (Å, º) top

F1—C1	1.329 (3)	C8—C9	1.511 (4)
F2—C2	1.341 (3)	C8—H8A	0.9700
F3—C3	1.339 (3)	C8—H8B	0.9700
F4—C4	1.339 (3)	C9—C10	1.504 (4)
F5—C16	1.350 (3)	C9—H9A	0.9700
F6—C17	1.341 (3)	C9—H9B	0.9700
F7—C18	1.339 (3)	C10—H10A	0.9700
F8—C19	1.350 (3)	C10—H10B	0.9700
N1—C7	1.340 (3)	C11—C12	1.498 (4)
N1—C13	1.465 (3)	C11—H11A	0.9700
N1—C8	1.467 (3)	C11—H11B	0.9700
N2—C14	1.334 (3)	C12—C13	1.514 (4)
N2—C10	1.465 (3)	C12—H12A	0.9700
N2—C11	1.482 (3)	C12—H12B	0.9700
O1—C7	1.229 (3)	C13—H13A	0.9700
O2—C14	1.222 (3)	C13—H13B	0.9700
C1—C6	1.374 (3)	C14—C15	1.505 (3)
C1—C2	1.375 (4)	C15—C16	1.378 (3)
C2—C3	1.367 (4)	C15—C20	1.391 (3)
C3—C4	1.367 (3)	C16—C17	1.367 (4)
C4—C5	1.371 (3)	C17—C18	1.368 (4)
C5—C6	1.380 (3)	C18—C19	1.372 (4)
C5—H5	0.9300	C19—C20	1.365 (4)
C6—C7	1.506 (3)	C20—H20	0.9300

C7—N1—C13	123.8 (2)	N2—C10—H10B	108.6
C7—N1—C8	118.8 (2)	C9—C10—H10B	108.6
C13—N1—C8	117.35 (19)	H10A—C10—H10B	107.6
C14—N2—C10	123.21 (19)	N2—C11—C12	115.7 (2)
C14—N2—C11	118.26 (19)	N2—C11—H11A	108.4
C10—N2—C11	118.07 (18)	C12—C11—H11A	108.4
F1—C1—C6	120.0 (2)	N2—C11—H11B	108.4
F1—C1—C2	118.3 (2)	C12—C11—H11B	108.4
C6—C1—C2	121.7 (2)	H11A—C11—H11B	107.4
F2—C2—C3	120.0 (2)	C11—C12—C13	116.1 (2)
F2—C2—C1	120.5 (2)	C11—C12—H12A	108.3
C3—C2—C1	119.6 (2)	C13—C12—H12A	108.3
F3—C3—C4	120.9 (2)	C11—C12—H12B	108.3
F3—C3—C2	120.0 (2)	C13—C12—H12B	108.3
C4—C3—C2	119.1 (2)	H12A—C12—H12B	107.4
F4—C4—C3	117.6 (2)	N1—C13—C12	114.3 (2)
F4—C4—C5	120.7 (2)	N1—C13—H13A	108.7
C3—C4—C5	121.7 (2)	C12—C13—H13A	108.7
C4—C5—C6	119.7 (2)	N1—C13—H13B	108.7
C4—C5—H5	120.2	C12—C13—H13B	108.7
C6—C5—H5	120.2	H13A—C13—H13B	107.6
C1—C6—C5	118.3 (2)	O2—C14—N2	124.0 (2)
C1—C6—C7	120.1 (2)	O2—C14—C15	118.3 (2)
C5—C6—C7	121.2 (2)	N2—C14—C15	117.67 (19)
O1—C7—N1	123.0 (2)	C16—C15—C20	118.7 (2)
O1—C7—C6	118.7 (2)	C16—C15—C14	120.6 (2)
N1—C7—C6	118.3 (2)	C20—C15—C14	120.5 (2)
N1—C8—C9	114.27 (19)	F5—C16—C17	119.0 (2)
N1—C8—H8A	108.7	F5—C16—C15	119.3 (2)
C9—C8—H8A	108.7	C17—C16—C15	121.7 (2)
N1—C8—H8B	108.7	F6—C17—C16	120.6 (3)
C9—C8—H8B	108.7	F6—C17—C18	119.9 (3)
H8A—C8—H8B	107.6	C16—C17—C18	119.5 (2)
C10—C9—C8	117.1 (2)	F7—C18—C17	120.2 (3)
C10—C9—H9A	108.0	F7—C18—C19	120.6 (3)
C8—C9—H9A	108.0	C17—C18—C19	119.2 (2)
C10—C9—H9B	108.0	F8—C19—C20	120.5 (3)
C8—C9—H9B	108.0	F8—C19—C18	117.5 (2)
H9A—C9—H9B	107.3	C20—C19—C18	122.1 (2)
N2—C10—C9	114.53 (18)	C19—C20—C15	118.8 (2)
N2—C10—H10A	108.6	C19—C20—H20	120.6
C9—C10—H10A	108.6	C15—C20—H20	120.6

F1—C1—C2—F2	0.0 (4)	C14—N2—C11—C12	144.2 (2)
C6—C1—C2—F2	179.4 (2)	C10—N2—C11—C12	−43.4 (3)
F1—C1—C2—C3	−179.9 (2)	N2—C11—C12—C13	−65.1 (3)
C6—C1—C2—C3	−0.5 (4)	C7—N1—C13—C12	−126.1 (2)
F2—C2—C3—F3	−0.5 (4)	C8—N1—C13—C12	56.7 (3)
C1—C2—C3—F3	179.4 (2)	C11—C12—C13—N1	57.1 (3)
F2—C2—C3—C4	−179.8 (2)	C10—N2—C14—O2	−176.4 (2)
C1—C2—C3—C4	0.2 (4)	C11—N2—C14—O2	−4.4 (3)
F3—C3—C4—F4	1.1 (3)	C10—N2—C14—C15	4.2 (3)
C2—C3—C4—F4	−179.7 (2)	C11—N2—C14—C15	176.21 (19)
F3—C3—C4—C5	−178.4 (2)	O2—C14—C15—C16	99.4 (3)
C2—C3—C4—C5	0.8 (4)	N2—C14—C15—C16	−81.2 (3)
F4—C4—C5—C6	179.0 (2)	O2—C14—C15—C20	−75.9 (3)
C3—C4—C5—C6	−1.5 (3)	N2—C14—C15—C20	103.5 (2)
F1—C1—C6—C5	179.2 (2)	C20—C15—C16—F5	179.0 (2)
C2—C1—C6—C5	−0.2 (3)	C14—C15—C16—F5	3.6 (3)
F1—C1—C6—C7	5.8 (3)	C20—C15—C16—C17	−1.4 (3)
C2—C1—C6—C7	−173.6 (2)	C14—C15—C16—C17	−176.8 (2)
C4—C5—C6—C1	1.2 (3)	F5—C16—C17—F6	0.0 (4)
C4—C5—C6—C7	174.5 (2)	C15—C16—C17—F6	−179.6 (2)
C13—N1—C7—O1	173.3 (2)	F5—C16—C17—C18	−179.7 (2)
C8—N1—C7—O1	−9.5 (3)	C15—C16—C17—C18	0.7 (4)
C13—N1—C7—C6	−7.8 (3)	F6—C17—C18—F7	−0.7 (4)
C8—N1—C7—C6	169.4 (2)	C16—C17—C18—F7	179.0 (2)
C1—C6—C7—O1	105.0 (3)	F6—C17—C18—C19	−179.4 (2)
C5—C6—C7—O1	−68.2 (3)	C16—C17—C18—C19	0.4 (4)
C1—C6—C7—N1	−73.9 (3)	F7—C18—C19—F8	0.4 (3)
C5—C6—C7—N1	112.9 (2)	C17—C18—C19—F8	179.1 (2)
C7—N1—C8—C9	76.8 (3)	F7—C18—C19—C20	−179.3 (2)
C13—N1—C8—C9	−105.8 (3)	C17—C18—C19—C20	−0.6 (4)
N1—C8—C9—C10	59.0 (3)	F8—C19—C20—C15	−179.9 (2)
C14—N2—C10—C9	−83.7 (3)	C18—C19—C20—C15	−0.2 (3)
C11—N2—C10—C9	104.3 (2)	C16—C15—C20—C19	1.1 (3)
C8—C9—C10—N2	−63.2 (3)	C14—C15—C20—C19	176.6 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄F₈N₂O₂
M_r	466.33
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	295
a, b, c (Å)	14.8085 (11), 20.5518 (16), 12.7062 (10)
V (Å³)	3867.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.36 × 0.30 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.942, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	27117, 3805, 2837
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.146, 1.04
No. of reflections	3805
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

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1,5-Bis(2,3,4,5-tetra­fluoro­benzo­yl)-1,5-diaza­cyclo­octa­ne

Supporting information

Key indicators

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1,5-Bis(2,3,4,5-tetrafluorobenzoyl)-1,5-diazacyclooctane