N,N′-[(2,3,5,6-Tetra­fluoro-1,4-phenyl­ene)dimethyl­ene]bis­(pyridine-4-carboxamide)

In the centrosymmetric mol­ecule of the title compound, C₂₀H₁₄F₄N₄O₂, the pyridine ring is twisted with respect to the benzene ring with a dihedral angle of 66.85 (10)°. In the crystal structure, mol­ecules are linked by inter­molecular hydrogen-bonding and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.049
• wR factor = 0.126
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N,N'-[(2,3,5,6-Tetrafluoro-1,4-phenylene)dimethylene]bis(pyridine-4-carboxamide)

Crystal data

C20H14F4N4O2	F(000) = 428
Mr = 418.35	Dx = 1.567 Mg m^−3
Monoclinic, P21/n	Melting point = 551–552 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.3488 (17) Å	Cell parameters from 1340 reflections
b = 5.1431 (11) Å	θ = 2.6–26.7°
c = 20.665 (4) Å	µ = 0.13 mm^−1
β = 91.843 (2)°	T = 298 K
V = 886.9 (3) Å^3	Block, colorless
Z = 2	0.30 × 0.20 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1302 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.044
Graphite monochromator	θmax = 28.5°, θmin = 2.6°
φ and ω scans	h = −11→11
7535 measured reflections	k = −6→6
2213 independent reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0524P)^2 + 0.1461P] where P = (Fo^2 + 2Fc^2)/3
2213 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9524 (2)	0.9500 (4)	0.81905 (9)	0.0345 (5)
C2	1.0601 (3)	1.1235 (4)	0.79308 (11)	0.0444 (5)
H2	1.1022	1.2594	0.8179	0.053*
C3	1.1037 (3)	1.0909 (5)	0.72949 (12)	0.0540 (6)
H3	1.1761	1.2087	0.7128	0.065*
C4	0.9463 (3)	0.7353 (5)	0.71657 (11)	0.0502 (6)
H4	0.9064	0.6008	0.6906	0.060*
C5	0.8955 (3)	0.7500 (4)	0.77951 (10)	0.0426 (5)
H5	0.8243	0.6277	0.7951	0.051*
C6	0.8965 (2)	0.9924 (4)	0.88635 (10)	0.0354 (5)
C7	0.7967 (3)	0.7973 (5)	0.98530 (10)	0.0466 (6)
H7A	0.7768	0.9780	0.9958	0.056*
H7B	0.8779	0.7323	1.0158	0.056*
C8	0.6439 (2)	0.6433 (4)	0.99278 (9)	0.0372 (5)
C9	0.6337 (3)	0.4422 (4)	1.03670 (9)	0.0388 (5)
C10	0.4945 (3)	0.3030 (4)	1.04358 (9)	0.0394 (5)
F1	0.76378 (15)	0.3760 (3)	1.07391 (6)	0.0541 (4)
F2	0.49451 (16)	0.1048 (2)	1.08655 (6)	0.0550 (4)
N1	1.0486 (2)	0.9015 (4)	0.69070 (9)	0.0533 (5)
N2	0.85681 (19)	0.7811 (3)	0.91993 (8)	0.0392 (4)
H2A	0.8750	0.6241	0.9045	0.047*
O1	0.88575 (18)	1.2160 (3)	0.90810 (7)	0.0483 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0323 (11)	0.0320 (11)	0.0394 (11)	0.0015 (8)	0.0039 (8)	0.0003 (8)
C2	0.0475 (13)	0.0374 (12)	0.0489 (13)	−0.0068 (10)	0.0094 (10)	0.0003 (10)
C3	0.0561 (15)	0.0525 (15)	0.0546 (14)	−0.0049 (12)	0.0185 (12)	0.0066 (12)
C4	0.0534 (14)	0.0519 (15)	0.0454 (13)	−0.0011 (12)	0.0067 (11)	−0.0076 (11)
C5	0.0448 (12)	0.0381 (12)	0.0454 (12)	−0.0063 (10)	0.0091 (10)	−0.0037 (10)
C6	0.0321 (11)	0.0316 (11)	0.0427 (11)	−0.0018 (8)	0.0039 (9)	−0.0011 (9)
C7	0.0536 (14)	0.0496 (14)	0.0374 (11)	−0.0129 (11)	0.0116 (10)	−0.0059 (10)
C8	0.0414 (12)	0.0383 (12)	0.0327 (10)	−0.0004 (9)	0.0113 (9)	−0.0039 (9)
C9	0.0410 (12)	0.0448 (13)	0.0310 (10)	0.0052 (10)	0.0062 (9)	0.0007 (9)
C10	0.0518 (13)	0.0363 (11)	0.0308 (10)	0.0020 (10)	0.0125 (9)	0.0061 (9)
F1	0.0465 (8)	0.0674 (9)	0.0483 (7)	0.0067 (7)	−0.0003 (6)	0.0078 (6)
F2	0.0686 (9)	0.0480 (8)	0.0487 (8)	−0.0002 (7)	0.0096 (6)	0.0173 (6)
N1	0.0574 (13)	0.0580 (13)	0.0453 (11)	0.0017 (10)	0.0117 (9)	0.0006 (10)
N2	0.0461 (10)	0.0309 (9)	0.0417 (9)	−0.0026 (8)	0.0158 (8)	−0.0038 (8)
O1	0.0641 (10)	0.0306 (8)	0.0506 (9)	−0.0031 (7)	0.0093 (7)	−0.0058 (7)

Geometric parameters (Å, º)

C1—C2	1.387 (3)	C6—N2	1.337 (3)
C1—C5	1.388 (3)	C7—N2	1.459 (2)
C1—C6	1.497 (3)	C7—C8	1.513 (3)
C2—C3	1.385 (3)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—N1	1.334 (3)	C8—C9	1.380 (3)
C3—H3	0.9300	C8—C10^i	1.386 (3)
C4—N1	1.332 (3)	C9—F1	1.354 (2)
C4—C5	1.383 (3)	C9—C10	1.377 (3)
C4—H4	0.9300	C10—F2	1.351 (2)
C5—H5	0.9300	C10—C8^i	1.386 (3)
C6—O1	1.239 (2)	N2—H2A	0.8829
C2—C1—C5	117.59 (19)	N2—C7—H7A	109.1
C2—C1—C6	119.41 (18)	C8—C7—H7A	109.1
C5—C1—C6	122.92 (18)	N2—C7—H7B	109.1
C3—C2—C1	118.9 (2)	C8—C7—H7B	109.1
C3—C2—H2	120.6	H7A—C7—H7B	107.9
C1—C2—H2	120.6	C9—C8—C10^i	115.98 (19)
N1—C3—C2	124.2 (2)	C9—C8—C7	121.9 (2)
N1—C3—H3	117.9	C10^i—C8—C7	122.09 (19)
C2—C3—H3	117.9	F1—C9—C10	118.34 (18)
N1—C4—C5	124.2 (2)	F1—C9—C8	119.80 (19)
N1—C4—H4	117.9	C10—C9—C8	121.85 (19)
C5—C4—H4	117.9	F2—C10—C9	118.56 (19)
C4—C5—C1	119.0 (2)	F2—C10—C8^i	119.26 (19)
C4—C5—H5	120.5	C9—C10—C8^i	122.17 (19)
C1—C5—H5	120.5	C4—N1—C3	116.1 (2)
O1—C6—N2	122.97 (18)	C6—N2—C7	122.20 (17)
O1—C6—C1	120.04 (18)	C6—N2—H2A	120.5
N2—C6—C1	116.98 (17)	C7—N2—H2A	117.0
N2—C7—C8	112.40 (17)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^ii	0.88	2.10	2.927 (2)	155
C4—H4···F2^iii	0.93	2.53	3.242 (3)	134
C7—H7B···O1^iv	0.97	2.50	3.393 (3)	153

Symmetry codes: (ii) x, y−1, z; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+2, −y+2, −z+2.