Redetermination of 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]dodeca-ne.

The structure of the title compound, C8H16N4, which consists of four fused seven-membered rings, has been redetermined at 173 K. This redetermination corrects the orientation of two H atoms, which were located at unrealistic positions in the original room-temperature study [Murray-Rust (1974 ▶). J. Chem. Soc. Perkin Trans. 2, pp. 1136-1141]. The complete mol-ecule is generated by -42m symmetry, with one quarter of a mol-ecule [one N atom (site symmetry m), two C atoms (one with site symmetry m and the other with site symmetry 2) and two H atoms] in the asymmetric unit. No directional inter-actions beyond van der Waals contacts are apparent in the crystal structure.

Related literature

For the original synthesis procedure, see: Bischoff (1898 ▶). For the previous determination of the structure, see: Murray-Rust (1974 ▶). For crystal structures containing the title compound as a fragment, see: Rivera et al. (2007 ▶); Glister et al. (2005 ▶). For a description of the Cambridge Crystallographic Database, see: Allen et al. (2002 ▶).

Experimental

Crystal data

C8H16N4

M = 168.25

Tetragonal,

a = 7.4065 (7) Å

c = 7.6235 (8) Å

V = 418.20 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.32 × 0.28 × 0.27 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001 ▶) T min = 0.973, T max = 0.977

4336 measured reflections

264 independent reflections

264 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.141

S = 1.12

264 reflections

18 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814002608/hb7192sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002608/hb7192Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002608/hb7192Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H16N4	Dx = 1.336 Mg m−3
Mr = 168.25	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I42m	Cell parameters from 11628 reflections
a = 7.4065 (7) Å	θ = 3.8–27.9°
c = 7.6235 (8) Å	µ = 0.09 mm−1
V = 418.20 (9) Å3	T = 173 K
Z = 2	Block, colourless
F(000) = 184	0.32 × 0.28 × 0.27 mm

Stoe IPDS II two-circle diffractometer	264 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.049
ω scans	θmax = 27.5°, θmin = 5.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→8
Tmin = 0.973, Tmax = 0.977	k = −9→9
4336 measured reflections	l = −9→9
264 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0809P)2 + 0.2587P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
264 reflections	Δρmax = 0.27 e Å−3
18 parameters	Δρmin = −0.17 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. ;

	x	y	z	Uiso*/Ueq
N1	0.1352 (2)	0.1352 (2)	0.0995 (4)	0.0373 (9)
C1	0.2345 (4)	0.0000	0.0000	0.0406 (10)
H1	0.3140	0.0649	−0.0832	0.049*
C2	0.0705 (4)	0.0705 (4)	0.2690 (5)	0.0604 (14)
H2	0.0235	0.1756	0.3350	0.073*

	U11	U22	U33	U12	U13	U23
N1	0.0317 (10)	0.0317 (10)	0.0483 (16)	−0.0099 (11)	0.0011 (8)	0.0011 (8)
C1	0.0228 (14)	0.0310 (16)	0.068 (2)	0.000	0.000	0.0063 (15)
C2	0.071 (2)	0.071 (2)	0.0392 (17)	−0.038 (2)	−0.0017 (11)	−0.0017 (11)

N1—C1i	1.456 (2)	C1—H1	0.9900
N1—C1	1.456 (2)	C2—C2iii	1.477 (8)
N1—C2	1.459 (5)	C2—H2	0.9900
C1—N1ii	1.456 (2)
C1i—N1—C1	115.0 (3)	N1—C1—H1	107.5
C1i—N1—C2	113.66 (12)	N1—C2—C2iii	117.68 (18)
C1—N1—C2	113.66 (12)	N1—C2—H2	107.9
N1ii—C1—N1	119.4 (3)	C2iii—C2—H2	107.9
N1ii—C1—H1	107.5
C1i—N1—C1—N1ii	−52.65 (18)	C1i—N1—C2—C2iii	67.1 (2)
C2—N1—C1—N1ii	80.8 (2)	C1—N1—C2—C2iii	−67.1 (2)