N,N'-Bis-[(E)-(6-methyl-2-pyridyl)-methyl-ene]hexane-1,6-diamine.

The title compound, C(20)H(26)N(4), is composed of two (6-methyl-2-pyridyl)methyl-ene units linked by a 1,6-diamine hexane chain. The mol-ecule has C(i) symmetry with the inversion center situated at the mid-point of the central C-C bond. The alkyl chain has an all-trans conformation, with all the non-H atoms sharing the same plane [maximum deviation 0.004 (3) Å]. The pyridylmethyl-ene groups are also planar [maximum deviation 0.009 (3) Å], making an angle of 53.78 (19)° with the hexane chain plane. In the crystal, the mol-ecules assemble in layers, stacking along the a axis. The stacks are hold together by attractive interactions between π electron systems.

Related literature

For salen ligands, their structures and possible applications, see: Cozzi (2004 ▶); Li et al. (2007 ▶); Renehan et al. (2005 ▶); Mohamed et al. (2006 ▶). For ruthenium–salen complexes, see: Wu & Gorden (2007 ▶). For the use of salen ligands to form metal-organic frameworks, see: Bu et al. (2001 ▶); van den Berga & Arean (2008 ▶).

Experimental

Crystal data

C20H26N4

M = 322.45

Orthorhombic,

a = 7.2713 (10) Å

b = 12.6671 (18) Å

c = 20.458 (3) Å

V = 1884.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.17 × 0.12 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.891, T max = 0.991

7591 measured reflections

2308 independent reflections

742 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.184

S = 0.88

2308 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016730/su2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016730/su2109Isup2.hkl

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

C20H26N4	F(000) = 696
Mr = 322.45	Dx = 1.137 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 546 reflections
a = 7.2713 (10) Å	θ = 3.2–20.3°
b = 12.6671 (18) Å	µ = 0.07 mm−1
c = 20.458 (3) Å	T = 293 K
V = 1884.3 (5) Å3	Prism, yellow
Z = 4	0.17 × 0.12 × 0.09 mm

Bruker APEX CCD area-detector diffractometer	2308 independent reflections
Radiation source: fine-focus sealed tube	742 reflections with I > 2σ(I)
graphite	Rint = 0.066
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→8
Tmin = 0.891, Tmax = 0.991	k = −16→12
7591 measured reflections	l = −22→25

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 0.88	w = 1/[σ2(Fo2) + (0.0774P)2] where P = (Fo2 + 2Fc2)/3
2308 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.14 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
N2	0.1193 (3)	0.29540 (19)	0.10261 (10)	0.0731 (7)
C1	0.0485 (4)	0.4665 (2)	0.14588 (13)	0.0633 (8)
N1	−0.0101 (3)	0.56245 (18)	0.12827 (10)	0.0667 (7)
C5	−0.0300 (4)	0.6357 (2)	0.17502 (13)	0.0683 (8)
C10	0.0506 (4)	0.05151 (18)	−0.00364 (12)	0.0711 (8)
H10A	0.0034	0.0880	−0.0418	0.085*
H10B	0.1796	0.0366	−0.0115	0.085*
C9	0.0355 (4)	0.1241 (2)	0.05473 (12)	0.0719 (8)
H9A	−0.0932	0.1400	0.0624	0.086*
H9B	0.0820	0.0877	0.0930	0.086*
C2	0.0901 (4)	0.4398 (2)	0.20945 (14)	0.0792 (9)
H2	0.1312	0.3724	0.2199	0.095*
C7	0.0688 (4)	0.3890 (2)	0.09307 (13)	0.0674 (8)
H7	0.0430	0.4102	0.0505	0.081*
C8	0.1391 (4)	0.2259 (2)	0.04644 (12)	0.0760 (9)
H8A	0.2684	0.2104	0.0399	0.091*
H8B	0.0945	0.2619	0.0077	0.091*
C6	−0.0943 (5)	0.7425 (2)	0.15397 (13)	0.0892 (10)
H6A	0.0012	0.7933	0.1616	0.134*
H6B	−0.2018	0.7617	0.1785	0.134*
H6C	−0.1238	0.7411	0.1082	0.134*
C4	0.0072 (4)	0.6140 (2)	0.23978 (14)	0.0762 (9)
H4	−0.0095	0.6658	0.2715	0.091*
C3	0.0690 (4)	0.5156 (3)	0.25715 (14)	0.0852 (10)
H3	0.0963	0.5002	0.3005	0.102*

	U11	U22	U33	U12	U13	U23
N2	0.0935 (18)	0.0568 (16)	0.0689 (14)	−0.0005 (13)	−0.0027 (13)	−0.0059 (12)
C1	0.071 (2)	0.061 (2)	0.0577 (16)	−0.0117 (15)	0.0005 (15)	−0.0023 (14)
N1	0.0852 (17)	0.0543 (15)	0.0605 (13)	−0.0067 (13)	0.0013 (12)	−0.0032 (12)
C5	0.080 (2)	0.064 (2)	0.0614 (17)	−0.0082 (16)	−0.0006 (16)	−0.0020 (15)
C10	0.091 (2)	0.0550 (18)	0.0675 (16)	0.0042 (15)	0.0070 (17)	0.0000 (14)
C9	0.091 (2)	0.0575 (18)	0.0677 (17)	0.0042 (17)	0.0051 (16)	−0.0029 (14)
C2	0.101 (3)	0.067 (2)	0.0701 (19)	−0.0010 (18)	−0.0052 (18)	−0.0026 (17)
C7	0.081 (2)	0.061 (2)	0.0605 (16)	−0.0091 (16)	−0.0001 (15)	−0.0005 (15)
C8	0.097 (2)	0.065 (2)	0.0654 (17)	0.0011 (17)	0.0064 (16)	−0.0070 (15)
C6	0.130 (3)	0.061 (2)	0.0771 (18)	0.0014 (19)	0.000 (2)	−0.0048 (16)
C4	0.095 (2)	0.068 (2)	0.0651 (19)	−0.0068 (19)	−0.0056 (16)	−0.0116 (15)
C3	0.114 (3)	0.081 (2)	0.0602 (17)	−0.004 (2)	−0.0119 (18)	0.0020 (18)

N2—C7	1.257 (3)	C9—H9A	0.9700
N2—C8	1.455 (3)	C9—H9B	0.9700
C1—N1	1.338 (3)	C2—C3	1.377 (4)
C1—C2	1.377 (4)	C2—H2	0.9300
C1—C7	1.467 (4)	C7—H7	0.9300
N1—C5	1.340 (3)	C8—H8A	0.9700
C5—C4	1.380 (4)	C8—H8B	0.9700
C5—C6	1.495 (4)	C6—H6A	0.9600
C10—C10i	1.506 (5)	C6—H6B	0.9600
C10—C9	1.511 (3)	C6—H6C	0.9600
C10—H10A	0.9700	C4—C3	1.373 (4)
C10—H10B	0.9700	C4—H4	0.9300
C9—C8	1.503 (3)	C3—H3	0.9300
C7—N2—C8	118.5 (2)	C1—C2—H2	120.9
N1—C1—C2	123.2 (3)	N2—C7—C1	123.1 (3)
N1—C1—C7	116.2 (2)	N2—C7—H7	118.5
C2—C1—C7	120.6 (3)	C1—C7—H7	118.5
C1—N1—C5	118.1 (2)	N2—C8—C9	112.4 (2)
N1—C5—C4	121.7 (3)	N2—C8—H8A	109.1
N1—C5—C6	117.1 (2)	C9—C8—H8A	109.1
C4—C5—C6	121.2 (3)	N2—C8—H8B	109.1
C10i—C10—C9	114.4 (3)	C9—C8—H8B	109.1
C10i—C10—H10A	108.7	H8A—C8—H8B	107.9
C9—C10—H10A	108.7	C5—C6—H6A	109.5
C10i—C10—H10B	108.7	C5—C6—H6B	109.5
C9—C10—H10B	108.7	H6A—C6—H6B	109.5
H10A—C10—H10B	107.6	C5—C6—H6C	109.5
C8—C9—C10	113.3 (2)	H6A—C6—H6C	109.5
C8—C9—H9A	108.9	H6B—C6—H6C	109.5
C10—C9—H9A	108.9	C3—C4—C5	119.6 (3)
C8—C9—H9B	108.9	C3—C4—H4	120.2
C10—C9—H9B	108.9	C5—C4—H4	120.2
H9A—C9—H9B	107.7	C4—C3—C2	119.1 (3)
C3—C2—C1	118.3 (3)	C4—C3—H3	120.5
C3—C2—H2	120.9	C2—C3—H3	120.5
C2—C1—N1—C5	−0.4 (4)	N1—C1—C7—N2	−178.7 (3)
C7—C1—N1—C5	−179.8 (2)	C2—C1—C7—N2	1.9 (4)
C1—N1—C5—C4	−0.3 (4)	C7—N2—C8—C9	−127.9 (3)
C1—N1—C5—C6	179.6 (3)	C10—C9—C8—N2	178.8 (2)
C10i—C10—C9—C8	179.5 (3)	N1—C5—C4—C3	1.0 (4)
N1—C1—C2—C3	0.4 (5)	C6—C5—C4—C3	−178.9 (3)
C7—C1—C2—C3	179.9 (3)	C5—C4—C3—C2	−0.9 (5)
C8—N2—C7—C1	−178.5 (2)	C1—C2—C3—C4	0.3 (5)