1,4-Bis(3-pyridylmethyl-eneamino-meth-yl)benzene.

The title compound, C(20)H(18)N(4), is a flexible 3,3'-bipyridyl-type ligand with a long spacer group between the two pyridyl functions. The mol-ecule crystallizes around an inversion center, with one half-mol-ecule in the asymmetric unit and a dihedral angle of 71.85 (8)° between the pyridine ring and the central benzene ring.

Related literature

For background information on bipyridyl-type Schiff base ligands, see: Cho et al. (2006 ▶); Haga et al. (1985 ▶); Mahmoudi et al. (2007 ▶); Wang et al. (2008 ▶). Haga et al. (1985 ▶) describe the synthesis of the title compound.

Experimental

Crystal data

C20H18N4

M = 314.38

Monoclinic,

a = 6.0990 (11) Å

b = 14.589 (3) Å

c = 9.9481 (18) Å

β = 107.851 (3)°

V = 842.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 291 (2) K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.98, T max = 0.98

6535 measured reflections

1661 independent reflections

1085 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.101

S = 1.01

1661 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.12 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/S1600536809000658/zl2166sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000658/zl2166Isup2.hkl

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

C20H18N4	F(000) = 332
Mr = 314.38	Dx = 1.239 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2797 reflections
a = 6.0990 (11) Å	θ = 2.6–27.2°
b = 14.589 (3) Å	µ = 0.08 mm−1
c = 9.9481 (18) Å	T = 291 K
β = 107.851 (3)°	Block, colorless
V = 842.5 (3) Å3	0.24 × 0.22 × 0.20 mm
Z = 2

Bruker SMART APEX CCD diffractometer	1661 independent reflections
Radiation source: sealed tube	1085 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.98, Tmax = 0.98	k = −17→17
6535 measured reflections	l = −11→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3
1661 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.12 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	0.0338 (3)	0.59733 (9)	0.90988 (16)	0.0402 (4)
C2	0.2284 (3)	0.63315 (11)	1.00966 (18)	0.0512 (4)
H2	0.3749	0.6142	1.0117	0.061*
C3	0.2005 (3)	0.69698 (11)	1.1050 (2)	0.0592 (5)
H3	0.3278	0.7216	1.1728	0.071*
C4	−0.0183 (4)	0.72359 (11)	1.0983 (2)	0.0627 (5)
H4	−0.0346	0.7673	1.1625	0.075*
C5	−0.1780 (3)	0.62821 (11)	0.91503 (19)	0.0522 (4)
H5	−0.3091	0.6036	0.8506	0.063*
C6	0.0482 (3)	0.53005 (10)	0.80278 (16)	0.0418 (4)
H6	−0.0874	0.5064	0.7416	0.050*
C7	0.2348 (3)	0.43652 (11)	0.68220 (17)	0.0475 (4)
H7A	0.0771	0.4255	0.6247	0.057*
H7B	0.2981	0.3791	0.7264	0.057*
C8	0.3738 (3)	0.46922 (10)	0.58876 (15)	0.0390 (4)
C9	0.3934 (3)	0.56235 (10)	0.56217 (16)	0.0430 (4)
H9	0.3223	0.6050	0.6044	0.052*
C10	0.5155 (3)	0.59265 (10)	0.47492 (17)	0.0424 (4)
H10	0.5239	0.6551	0.4585	0.051*
N1	−0.2079 (3)	0.69096 (10)	1.00596 (19)	0.0667 (5)
N2	0.2369 (2)	0.50359 (9)	0.79117 (15)	0.0489 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0437 (9)	0.0402 (7)	0.0394 (9)	−0.0009 (6)	0.0165 (7)	0.0070 (6)
C2	0.0458 (10)	0.0571 (10)	0.0500 (10)	0.0002 (8)	0.0134 (8)	−0.0032 (8)
C3	0.0643 (12)	0.0516 (10)	0.0579 (12)	−0.0079 (8)	0.0134 (9)	−0.0118 (8)
C4	0.0786 (14)	0.0431 (9)	0.0738 (13)	−0.0012 (9)	0.0345 (11)	−0.0131 (9)
C5	0.0470 (9)	0.0501 (9)	0.0600 (11)	0.0011 (8)	0.0169 (8)	−0.0034 (8)
C6	0.0425 (9)	0.0458 (8)	0.0374 (9)	−0.0011 (6)	0.0127 (7)	0.0029 (6)
C7	0.0467 (9)	0.0508 (8)	0.0462 (9)	0.0005 (7)	0.0161 (7)	−0.0041 (7)
C8	0.0379 (8)	0.0423 (7)	0.0333 (9)	0.0013 (6)	0.0055 (6)	−0.0063 (6)
C9	0.0464 (9)	0.0423 (7)	0.0414 (9)	0.0065 (7)	0.0149 (7)	−0.0081 (7)
C10	0.0477 (9)	0.0346 (7)	0.0442 (9)	0.0017 (6)	0.0129 (7)	−0.0025 (6)
N1	0.0609 (10)	0.0550 (9)	0.0887 (13)	0.0041 (8)	0.0297 (9)	−0.0173 (8)
N2	0.0478 (8)	0.0624 (9)	0.0393 (8)	0.0002 (6)	0.0175 (6)	−0.0074 (6)

C1—C5	1.384 (2)	C6—H6	0.9300
C1—C2	1.395 (2)	C7—N2	1.458 (2)
C1—C6	1.471 (2)	C7—C8	1.514 (2)
C2—C3	1.376 (2)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—C4	1.372 (3)	C8—C10i	1.391 (2)
C3—H3	0.9300	C8—C9	1.396 (2)
C4—N1	1.325 (3)	C9—C10	1.378 (2)
C4—H4	0.9300	C9—H9	0.9300
C5—N1	1.338 (2)	C10—C8i	1.391 (2)
C5—H5	0.9300	C10—H10	0.9300
C6—N2	1.253 (2)
C5—C1—C2	116.88 (15)	N2—C7—C8	111.49 (13)
C5—C1—C6	120.51 (15)	N2—C7—H7A	109.3
C2—C1—C6	122.61 (14)	C8—C7—H7A	109.3
C3—C2—C1	119.09 (16)	N2—C7—H7B	109.3
C3—C2—H2	120.5	C8—C7—H7B	109.3
C1—C2—H2	120.5	H7A—C7—H7B	108.0
C4—C3—C2	118.78 (18)	C10i—C8—C9	117.60 (13)
C4—C3—H3	120.6	C10i—C8—C7	121.10 (13)
C2—C3—H3	120.6	C9—C8—C7	121.30 (12)
N1—C4—C3	124.15 (17)	C10—C9—C8	121.72 (13)
N1—C4—H4	117.9	C10—C9—H9	119.1
C3—C4—H4	117.9	C8—C9—H9	119.1
N1—C5—C1	124.74 (18)	C9—C10—C8i	120.68 (13)
N1—C5—H5	117.6	C9—C10—H10	119.7
C1—C5—H5	117.6	C8i—C10—H10	119.7
N2—C6—C1	122.21 (15)	C4—N1—C5	116.34 (16)
N2—C6—H6	118.9	C6—N2—C7	118.48 (14)
C1—C6—H6	118.9

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N2	0.93	2.55	2.858 (2)	100