2,3,5,6-Tetra-fluoro-1,4-bis-(2-pyridylmethyl-eneamino-meth-yl)benzene.

The title compound, C(20)H(14)F(4)N(4), is a flexible bis-pyridine-type ligand with an extended fluorinated spacer group between the two pyridyl functions. The centroid of the central aromatic ring is situated on a crystallographic center of inversion. The dihedral angle between the pyridine ring and the central benzene ring is 63.85 (9)°. The crystal structure exhibits inter-molecular C-H⋯F hydrogen-bonding inter-actions.

Related literature

For background information on bis-pyridine-type Schiff base ligands see: Barboiu et al. (2006 ▶); Keegan et al. (2002 ▶); Yue et al. (2004 ▶). Haga et al. (1985 ▶) describe the synthesis of the title compound.

Experimental

Crystal data

C20H14F4N4

M = 386.35

Monoclinic,

a = 9.637 (3) Å

b = 7.783 (3) Å

c = 12.070 (4) Å

β = 105.940 (4)°

V = 870.5 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 296 (2) K

0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.963, T max = 0.974

7194 measured reflections

2014 independent reflections

1341 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.151

S = 1.05

2014 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001172/im2091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001172/im2091Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H14F4N4	F(000) = 396
Mr = 386.35	Dx = 1.474 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3894 reflections
a = 9.637 (3) Å	θ = 2.6–27.2°
b = 7.783 (3) Å	µ = 0.12 mm−1
c = 12.070 (4) Å	T = 296 K
β = 105.940 (4)°	Block, colorless
V = 870.5 (5) Å3	0.26 × 0.24 × 0.22 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2014 independent reflections
Radiation source: fine-focus sealed tube	1341 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
Tmin = 0.963, Tmax = 0.974	k = −10→10
7194 measured reflections	l = −15→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.1642P] where P = (Fo2 + 2Fc2)/3
2014 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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
C1	0.6996 (3)	0.1926 (3)	0.52870 (19)	0.0733 (6)
H1	0.7326	0.2286	0.6049	0.088*
C2	0.5633 (3)	0.2358 (3)	0.4693 (2)	0.0781 (7)
H2	0.5047	0.2981	0.5044	0.094*
C3	0.5132 (2)	0.1855 (3)	0.3558 (2)	0.0761 (7)
H3	0.4201	0.2127	0.3128	0.091*
C4	0.6041 (2)	0.0941 (3)	0.30767 (18)	0.0624 (5)
H4	0.5734	0.0591	0.2311	0.075*
C5	0.74130 (19)	0.0548 (2)	0.37431 (15)	0.0482 (4)
C6	0.8435 (2)	−0.0426 (2)	0.32794 (16)	0.0507 (4)
H6	0.9325	−0.0738	0.3770	0.061*
C7	0.9207 (2)	−0.1847 (3)	0.18519 (18)	0.0643 (6)
H7A	0.8812	−0.2964	0.1577	0.077*
H7B	1.0053	−0.2024	0.2496	0.077*
C8	0.9627 (2)	−0.0904 (2)	0.08987 (16)	0.0538 (5)
C9	1.0951 (2)	−0.0132 (3)	0.10554 (16)	0.0547 (5)
C10	1.1317 (2)	0.0740 (2)	0.01844 (18)	0.0556 (5)
F1	1.19419 (14)	−0.02363 (18)	0.20914 (11)	0.0756 (4)
F2	1.26344 (13)	0.14574 (17)	0.04184 (11)	0.0762 (4)
N1	0.79039 (18)	0.1014 (2)	0.48488 (14)	0.0622 (5)
N2	0.81318 (17)	−0.0848 (2)	0.22290 (14)	0.0567 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0789 (15)	0.0860 (16)	0.0611 (12)	0.0097 (13)	0.0293 (11)	−0.0086 (11)
C2	0.0766 (15)	0.0762 (16)	0.0951 (18)	0.0164 (12)	0.0465 (13)	−0.0028 (13)
C3	0.0537 (11)	0.0797 (16)	0.0951 (18)	0.0162 (11)	0.0207 (11)	0.0089 (13)
C4	0.0584 (11)	0.0667 (13)	0.0620 (12)	0.0040 (10)	0.0161 (9)	−0.0002 (10)
C5	0.0519 (10)	0.0463 (10)	0.0503 (10)	−0.0013 (8)	0.0206 (8)	0.0049 (8)
C6	0.0498 (10)	0.0523 (11)	0.0539 (10)	−0.0006 (8)	0.0207 (8)	0.0059 (8)
C7	0.0798 (13)	0.0555 (12)	0.0732 (13)	0.0025 (10)	0.0472 (11)	0.0011 (10)
C8	0.0672 (12)	0.0464 (11)	0.0597 (11)	−0.0007 (9)	0.0373 (10)	−0.0084 (8)
C9	0.0618 (11)	0.0549 (11)	0.0537 (10)	−0.0018 (9)	0.0267 (9)	−0.0124 (8)
C10	0.0577 (11)	0.0512 (11)	0.0688 (12)	−0.0102 (9)	0.0354 (10)	−0.0153 (9)
F1	0.0769 (8)	0.0893 (10)	0.0619 (8)	−0.0030 (7)	0.0213 (6)	−0.0061 (6)
F2	0.0663 (7)	0.0819 (9)	0.0898 (9)	−0.0222 (6)	0.0376 (7)	−0.0141 (7)
N1	0.0599 (10)	0.0747 (11)	0.0535 (9)	0.0079 (8)	0.0179 (7)	−0.0038 (8)
N2	0.0602 (9)	0.0624 (10)	0.0566 (9)	−0.0033 (8)	0.0316 (7)	0.0011 (7)

C1—N1	1.343 (3)	C6—H6	0.9300
C1—C2	1.355 (3)	C7—N2	1.464 (2)
C1—H1	0.9300	C7—C8	1.511 (3)
C2—C3	1.378 (3)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—C4	1.375 (3)	C8—C9	1.375 (3)
C3—H3	0.9300	C8—C10i	1.379 (3)
C4—C5	1.380 (3)	C9—F1	1.351 (2)
C4—H4	0.9300	C9—C10	1.376 (3)
C5—N1	1.338 (2)	C10—F2	1.344 (2)
C5—C6	1.470 (3)	C10—C8i	1.379 (3)
C6—N2	1.264 (2)
N1—C1—C2	124.4 (2)	N2—C7—C8	109.82 (16)
N1—C1—H1	117.8	N2—C7—H7A	109.7
C2—C1—H1	117.8	C8—C7—H7A	109.7
C1—C2—C3	118.6 (2)	N2—C7—H7B	109.7
C1—C2—H2	120.7	C8—C7—H7B	109.7
C3—C2—H2	120.7	H7A—C7—H7B	108.2
C4—C3—C2	118.5 (2)	C9—C8—C10i	115.87 (17)
C4—C3—H3	120.7	C9—C8—C7	122.69 (19)
C2—C3—H3	120.7	C10i—C8—C7	121.43 (18)
C3—C4—C5	119.2 (2)	F1—C9—C8	119.61 (17)
C3—C4—H4	120.4	F1—C9—C10	118.19 (18)
C5—C4—H4	120.4	C8—C9—C10	122.21 (19)
N1—C5—C4	122.76 (18)	F2—C10—C9	118.03 (19)
N1—C5—C6	115.41 (16)	F2—C10—C8i	120.04 (17)
C4—C5—C6	121.82 (18)	C9—C10—C8i	121.93 (18)
N2—C6—C5	121.41 (17)	C5—N1—C1	116.50 (17)
N2—C6—H6	119.3	C6—N2—C7	117.46 (17)
C5—C6—H6	119.3
N1—C1—C2—C3	−0.8 (4)	C10i—C8—C9—C10	−0.5 (3)
C1—C2—C3—C4	−0.2 (4)	C7—C8—C9—C10	−179.29 (17)
C2—C3—C4—C5	0.5 (4)	F1—C9—C10—F2	−0.8 (3)
C3—C4—C5—N1	0.3 (3)	C8—C9—C10—F2	179.80 (16)
C3—C4—C5—C6	179.96 (19)	F1—C9—C10—C8i	179.86 (16)
N1—C5—C6—N2	−175.63 (17)	C8—C9—C10—C8i	0.5 (3)
C4—C5—C6—N2	4.7 (3)	C4—C5—N1—C1	−1.2 (3)
N2—C7—C8—C9	108.5 (2)	C6—C5—N1—C1	179.09 (18)
N2—C7—C8—C10i	−70.3 (2)	C2—C1—N1—C5	1.5 (4)
C10i—C8—C9—F1	−179.83 (16)	C5—C6—N2—C7	−178.80 (16)
C7—C8—C9—F1	1.3 (3)	C8—C7—N2—C6	−122.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F2ii	0.93	2.53	3.370 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F2i	0.93	2.53	3.370 (3)	151

Symmetry code: (i) .