1,1'-(Ethane-1,2-di-yl)bis-(1,4,7-triazonane).

In the centrosymmetric title compound (dtne), C(14)H(32)N(6), two 1,4,7-triaza-cyclo-nonane (tacn, or 1,4,7-triazonane) moieties are linked together each at an amino position by a single ethyl-ene spacer. The mol-ecular packing is supported by pairs of inter-molecular N-H⋯N hydrogen bonds, which form R(2) (2)(22) ring motifs and link the mol-ecules into infinite chains running parallel to the a axis.

Related literature

For an investigation into the coordination chemistry of dtne derivatives and similarly bridged polyaza macrocyclic frameworks, see: Schröder et al. (2000 ▶). For dinuclear metal complexes of related ligands, see: Sinnecker et al. (2004 ▶); Marlin et al. (2005 ▶). For the crystal structure of the related compound 1,4,7-triaza­cyclo­nonane (tacn), see: Battle et al. (2005 ▶). For the structures of other metal complexes of dtne, see: Li et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the preparation of a similar compound, see: Burdinski et al. (2000 ▶).

Experimental

Crystal data

C14H32N6

M = 284.46

Triclinic,

a = 6.2732 (3) Å

b = 6.4988 (3) Å

c = 10.7152 (6) Å

α = 99.751 (2)°

β = 93.115 (2)°

γ = 110.410 (3)°

V = 400.45 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.4 × 0.28 × 0.28 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.649, T max = 0.985

4952 measured reflections

1806 independent reflections

1599 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.208

S = 1.23

1806 reflections

99 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.33 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019562/sj5006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019562/sj5006Isup2.hkl

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

C14H32N6	Z = 1
Mr = 284.46	F(000) = 158
Triclinic, P1	Dx = 1.18 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2732 (3) Å	Cell parameters from 6758 reflections
b = 6.4988 (3) Å	θ = 1.0–27.5°
c = 10.7152 (6) Å	µ = 0.08 mm−1
α = 99.751 (2)°	T = 150 K
β = 93.115 (2)°	Block, colourless
γ = 110.410 (3)°	0.4 × 0.28 × 0.28 mm
V = 400.45 (3) Å3

Bruker–Nonius KappaCCD diffractometer	1806 independent reflections
Radiation source: fine-focus sealed tube	1599 reflections with I > 2σ(I)
graphite	Rint = 0.099
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −7→8
Tmin = 0.649, Tmax = 0.985	k = −8→8
4952 measured reflections	l = −13→13

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ2(Fo2) + (0.0859P)2 + 0.2591P] where P = (Fo2 + 2Fc2)/3
1806 reflections	(Δ/σ)max < 0.001
99 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	0.1344 (3)	0.5390 (3)	0.32247 (17)	0.0229 (4)
H1	0.145 (5)	0.533 (5)	0.233 (3)	0.033 (7)*
N2	0.6399 (3)	0.5507 (3)	0.29452 (16)	0.0202 (4)
H2	0.775 (5)	0.583 (4)	0.312 (2)	0.019 (6)*
N3	0.1962 (3)	0.1707 (3)	0.15019 (15)	0.0200 (4)
C1	0.3489 (3)	0.6779 (3)	0.4061 (2)	0.0231 (5)
H1A	0.3671	0.5978	0.4744	0.028*
H1B	0.3328	0.819	0.4475	0.028*
C2	0.5687 (3)	0.7378 (3)	0.3420 (2)	0.0234 (5)
H2A	0.5468	0.808	0.2696	0.028*
H2B	0.6945	0.8513	0.404	0.028*
C3	0.5883 (3)	0.4564 (3)	0.15762 (18)	0.0234 (5)
H3A	0.7345	0.473	0.1221	0.028*
H3B	0.5167	0.5461	0.1168	0.028*
C4	0.4308 (3)	0.2106 (3)	0.12080 (18)	0.0225 (5)
H4A	0.4267	0.1575	0.0282	0.027*
H4B	0.4954	0.1211	0.1664	0.027*
C5	0.1748 (3)	0.1640 (3)	0.28616 (18)	0.0211 (5)
H5A	0.329	0.2224	0.3355	0.025*
H5B	0.0966	0.0072	0.2955	0.025*
C6	0.0377 (3)	0.3056 (3)	0.33779 (19)	0.0230 (5)
H6A	−0.1207	0.2366	0.2934	0.028*
H6B	0.0293	0.3037	0.4296	0.028*
C7	0.0265 (4)	−0.0249 (3)	0.06487 (18)	0.0241 (5)
H7A	−0.1166	−0.0741	0.1049	0.029*
H7B	0.0849	−0.1493	0.0528	0.029*

	U11	U22	U33	U12	U13	U23
N1	0.0170 (8)	0.0243 (9)	0.0240 (9)	0.0054 (7)	0.0015 (6)	0.0006 (7)
N2	0.0140 (8)	0.0237 (9)	0.0189 (8)	0.0049 (6)	0.0007 (6)	−0.0013 (6)
N3	0.0168 (8)	0.0211 (8)	0.0152 (8)	0.0016 (6)	0.0000 (6)	−0.0021 (6)
C1	0.0182 (9)	0.0242 (10)	0.0229 (10)	0.0068 (8)	0.0025 (7)	−0.0037 (8)
C2	0.0190 (9)	0.0193 (9)	0.0276 (10)	0.0033 (7)	0.0038 (7)	0.0009 (8)
C3	0.0199 (9)	0.0266 (10)	0.0183 (9)	0.0033 (8)	0.0038 (7)	0.0010 (8)
C4	0.0205 (10)	0.0246 (10)	0.0181 (9)	0.0061 (8)	0.0024 (7)	−0.0028 (7)
C5	0.0209 (9)	0.0214 (9)	0.0166 (9)	0.0034 (7)	0.0007 (7)	0.0018 (7)
C6	0.0174 (9)	0.0243 (10)	0.0226 (10)	0.0028 (7)	0.0043 (7)	0.0016 (8)
C7	0.0231 (10)	0.0193 (9)	0.0205 (10)	−0.0007 (7)	−0.0025 (7)	−0.0014 (8)

N1—C6	1.466 (3)	C3—C4	1.526 (3)
N1—C1	1.475 (2)	C3—H3A	0.99
N1—H1	0.96 (3)	C3—H3B	0.99
N2—C2	1.460 (3)	C4—H4A	0.99
N2—C3	1.462 (2)	C4—H4B	0.99
N2—H2	0.80 (3)	C5—C6	1.524 (3)
N3—C7	1.464 (2)	C5—H5A	0.99
N3—C4	1.464 (2)	C5—H5B	0.99
N3—C5	1.477 (2)	C6—H6A	0.99
C1—C2	1.531 (3)	C6—H6B	0.99
C1—H1A	0.99	C7—C7i	1.525 (4)
C1—H1B	0.99	C7—H7A	0.99
C2—H2A	0.99	C7—H7B	0.99
C2—H2B	0.99
C6—N1—C1	114.96 (17)	H3A—C3—H3B	107.5
C6—N1—H1	106.1 (17)	N3—C4—C3	113.41 (16)
C1—N1—H1	114.6 (17)	N3—C4—H4A	108.9
C2—N2—C3	117.19 (17)	C3—C4—H4A	108.9
C2—N2—H2	111.5 (17)	N3—C4—H4B	108.9
C3—N2—H2	106.5 (18)	C3—C4—H4B	108.9
C7—N3—C4	112.85 (15)	H4A—C4—H4B	107.7
C7—N3—C5	112.41 (15)	N3—C5—C6	109.75 (16)
C4—N3—C5	112.25 (15)	N3—C5—H5A	109.7
N1—C1—C2	116.37 (17)	C6—C5—H5A	109.7
N1—C1—H1A	108.2	N3—C5—H5B	109.7
C2—C1—H1A	108.2	C6—C5—H5B	109.7
N1—C1—H1B	108.2	H5A—C5—H5B	108.2
C2—C1—H1B	108.2	N1—C6—C5	113.78 (16)
H1A—C1—H1B	107.3	N1—C6—H6A	108.8
N2—C2—C1	115.49 (16)	C5—C6—H6A	108.8
N2—C2—H2A	108.4	N1—C6—H6B	108.8
C1—C2—H2A	108.4	C5—C6—H6B	108.8
N2—C2—H2B	108.4	H6A—C6—H6B	107.7
C1—C2—H2B	108.4	N3—C7—C7i	112.1 (2)
H2A—C2—H2B	107.5	N3—C7—H7A	109.2
N2—C3—C4	115.55 (17)	C7i—C7—H7A	109.2
N2—C3—H3A	108.4	N3—C7—H7B	109.2
C4—C3—H3A	108.4	C7i—C7—H7B	109.2
N2—C3—H3B	108.4	H7A—C7—H7B	107.9
C4—C3—H3B	108.4
C6—N1—C1—C2	106.9 (2)	C7—N3—C5—C6	−97.75 (19)
C3—N2—C2—C1	101.1 (2)	C4—N3—C5—C6	133.75 (17)
N1—C1—C2—N2	−67.9 (2)	C1—N1—C6—C5	−71.3 (2)
C2—N2—C3—C4	−118.6 (2)	N3—C5—C6—N1	−56.6 (2)
C7—N3—C4—C3	151.78 (17)	C4—N3—C7—C7i	−77.7 (3)
C5—N3—C4—C3	−79.9 (2)	C5—N3—C7—C7i	154.1 (2)
N2—C3—C4—N3	67.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1ii	0.80 (3)	2.37 (3)	3.129 (3)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.80 (3)	2.37 (3)	3.129 (3)	159 (2)

Symmetry code: (i) .