2,3-5,6-Tetra­fluoro-1,4-di-4-pyridylbenzene

In the title centrosymmetric mol­ecule, C₁₆H₈F₄N₂, the dihedral angle between the pyridine and benzene rings is 50.47 (5)°, which is inter­mediate between those observed when the central ring is benzene and when it is an anthracene. The crystal structure consists of layers of mol­ecules parallel to (20).

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.059
• wR factor = 0.137
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

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Computing details

Data collection: MARXDS (Klein, 2000); cell refinement: AUTOMAR (Klein & Bartels, 2000); data reduction: MARSCALE (Klein, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

2,3–5,6-Tetrafluoro-1,4-di-4-pyridylbenzene

Crystal data

C16H8F4N2	F(000) = 616
Mr = 304.24	Dx = 1.639 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 147 reflections
a = 17.126 (10) Å	θ = 6.3–21.6°
b = 5.919 (5) Å	µ = 0.14 mm^−1
c = 12.376 (8) Å	T = 294 K
β = 100.56 (3)°	Prism, white
V = 1233.3 (15) Å^3	0.3 × 0.2 × 0.1 mm
Z = 4

Data collection

MAR345 image-plate diffractometer	1473 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 30.0°, θmin = 2.4°
φ scans	h = −23→22
6143 measured reflections	k = 0→7
1693 independent reflections	l = 0→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0816P)^2 + 0.0195P] where P = (Fo^2 + 2Fc^2)/3
S = 1.21	(Δ/σ)max = 0.001
1693 reflections	Δρmax = 0.49 e Å^−3
101 parameters	Δρmin = −0.42 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (3)

Special details

Experimental. Data collection in MAR345 diffractometer was carried out with fixed the image-plate detector at a distance of 84 mm. In total 60 Images were collected with 3°/image and 420 s of exposition per image.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N	0.20933 (7)	0.50516 (17)	0.41828 (9)	0.0519 (3)
F1	−0.00231 (4)	0.14631 (9)	0.13829 (5)	0.0458 (2)
F2	−0.10191 (4)	0.14893 (10)	−0.05090 (5)	0.0461 (2)
C1	0.15711 (7)	0.31785 (17)	0.24699 (10)	0.0433 (3)
H1	0.1573	0.1914	0.2024	0.052*
C2	0.20533 (7)	0.32728 (19)	0.35079 (10)	0.0497 (3)
H2	0.2366	0.2021	0.3745	0.060*
C3	0.16328 (8)	0.68117 (19)	0.38226 (9)	0.0475 (3)
H3	0.1654	0.8070	0.4277	0.057*
C4	0.11220 (7)	0.68866 (17)	0.28090 (9)	0.0413 (3)
H4	0.0811	0.8155	0.2598	0.050*
C5	0.10880 (6)	0.50163 (16)	0.21184 (8)	0.0360 (2)
C6	0.05390 (5)	0.49946 (14)	0.10312 (7)	0.0345 (2)
C7	0.00131 (6)	0.32302 (15)	0.07101 (7)	0.0348 (3)
C8	−0.05135 (6)	0.32455 (15)	−0.02883 (8)	0.0358 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0497 (5)	0.0572 (6)	0.0417 (5)	−0.0049 (4)	−0.0100 (4)	0.0028 (4)
F1	0.0562 (4)	0.0415 (4)	0.0367 (4)	−0.0036 (2)	0.0005 (3)	0.0077 (2)
F2	0.0501 (4)	0.0420 (4)	0.0424 (4)	−0.0108 (2)	−0.0015 (3)	−0.0006 (2)
C1	0.0438 (6)	0.0407 (5)	0.0417 (6)	0.0034 (4)	−0.0019 (4)	−0.0006 (4)
C2	0.0468 (6)	0.0481 (6)	0.0471 (6)	0.0028 (4)	−0.0099 (5)	0.0063 (4)
C3	0.0531 (6)	0.0489 (6)	0.0358 (5)	−0.0063 (4)	−0.0040 (4)	−0.0043 (4)
C4	0.0447 (6)	0.0416 (5)	0.0345 (5)	0.0011 (4)	−0.0010 (4)	−0.0014 (3)
C5	0.0352 (5)	0.0404 (5)	0.0305 (5)	−0.0012 (3)	0.0012 (3)	0.0005 (3)
C6	0.0364 (5)	0.0367 (5)	0.0290 (5)	0.0029 (3)	0.0020 (4)	−0.0012 (3)
C7	0.0391 (5)	0.0346 (5)	0.0291 (5)	0.0019 (3)	0.0021 (4)	0.0012 (3)
C8	0.0379 (5)	0.0344 (5)	0.0335 (5)	−0.0034 (3)	0.0021 (4)	−0.0022 (3)

Geometric parameters (Å, º)

N—C3	1.3331 (17)	C3—H3	0.93
N—C2	1.3379 (17)	C4—C5	1.3933 (16)
F1—C7	1.3454 (13)	C4—H4	0.93
F2—C8	1.3485 (13)	C5—C6	1.4936 (16)
C1—C5	1.3875 (16)	C6—C8^i	1.3848 (15)
C1—C2	1.3952 (16)	C6—C7	1.3887 (14)
C1—H1	0.93	C7—C8	1.3899 (15)
C2—H2	0.93	C8—C6^i	1.3848 (15)
C3—C4	1.3923 (16)
C3—N—C2	116.53 (11)	C1—C5—C4	118.36 (10)
C5—C1—C2	118.40 (10)	C1—C5—C6	121.09 (9)
C5—C1—H1	120.8	C4—C5—C6	120.54 (9)
C2—C1—H1	120.8	C8^i—C6—C7	115.84 (10)
N—C2—C1	124.08 (10)	C8^i—C6—C5	121.98 (9)
N—C2—H2	118.0	C7—C6—C5	122.17 (8)
C1—C2—H2	118.0	F1—C7—C6	120.57 (9)
N—C3—C4	124.17 (10)	F1—C7—C8	117.34 (8)
N—C3—H3	117.9	C6—C7—C8	122.05 (8)
C4—C3—H3	117.9	F2—C8—C6^i	120.30 (9)
C3—C4—C5	118.43 (10)	F2—C8—C7	117.58 (8)
C3—C4—H4	120.8	C6^i—C8—C7	122.11 (9)
C5—C4—H4	120.8

Symmetry code: (i) −x, −y+1, −z.