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The structure of the title compound, C
6H
14N
4, has previously been determined at room temperature by Böttcher, Buchkremer-Hermanns, Hönle & von Schnering [
Z.
Kristallogr. (1987),
181, 223–226], who found only one position for the amine H atom. We report here the low-temperature structure of the title compound, showing that the amine H atom is disordered over two positions. This H atom must be located either in the equatorial or in the axial position so that N—H
N hydrogen bonds can be formed. A mirror plane contains the bond that the two rings have in common and a twofold rotation axis runs through the mid-points of all three C—C bonds.
Supporting information
CCDC reference: 253022
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.050
- wR factor = 0.144
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.98
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.25 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
trans-2,5,7,10-tetraazabicyclo[4.4.0]decane
top
Crystal data top
C6H14N4 | F(000) = 156 |
Mr = 142.21 | Dx = 1.282 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2y | Cell parameters from 2510 reflections |
a = 5.283 (2) Å | θ = 4.2–27.7° |
b = 15.937 (4) Å | µ = 0.09 mm−1 |
c = 4.6205 (18) Å | T = 173 K |
β = 108.78 (3)° | Rod, colourless |
V = 368.3 (2) Å3 | 0.32 × 0.14 × 0.13 mm |
Z = 2 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 362 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 27.8°, θmin = 4.3° |
ω scans | h = −6→6 |
2406 measured reflections | k = −18→20 |
449 independent reflections | l = −6→5 |
Refinement top
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | All H-atom parameters refined |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0894P)2] where P = (Fo2 + 2Fc2)/3 |
449 reflections | (Δ/σ)max < 0.001 |
45 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.1960 (3) | 0.42558 (6) | 0.8009 (2) | 0.0312 (5) | |
H1' | 0.356 (8) | 0.4282 (14) | 0.877 (7) | 0.030 (10)* | 0.54 (4) |
H1'' | 0.062 (6) | 0.4260 (13) | 0.890 (6) | 0.013 (9)* | 0.46 (4) |
C1 | 0.1446 (3) | 0.5000 | 0.6067 (3) | 0.0277 (5) | |
H1 | 0.268 (4) | 0.5000 | 0.479 (4) | 0.023 (4)* | |
C2 | 0.1424 (2) | 0.34970 (8) | 0.6111 (3) | 0.0341 (5) | |
H2A | 0.168 (4) | 0.2997 (10) | 0.740 (4) | 0.039 (4)* | |
H2B | 0.283 (3) | 0.3459 (9) | 0.500 (4) | 0.035 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0308 (8) | 0.0329 (7) | 0.0247 (7) | 0.0010 (3) | 0.0018 (5) | 0.0016 (3) |
C1 | 0.0259 (9) | 0.0318 (9) | 0.0222 (9) | 0.000 | 0.0035 (7) | 0.000 |
C2 | 0.0353 (8) | 0.0311 (7) | 0.0310 (8) | 0.0030 (4) | 0.0041 (5) | 0.0011 (4) |
Geometric parameters (Å, º) top
N1—C1 | 1.4591 (13) | C1—C1ii | 1.528 (3) |
N1—C2 | 1.4669 (14) | C1—H1 | 1.011 (19) |
N1—H1' | 0.80 (4) | C2—C2iii | 1.524 (2) |
N1—H1'' | 0.93 (3) | C2—H2A | 0.977 (17) |
C1—N1i | 1.4590 (13) | C2—H2B | 1.031 (16) |
| | | |
C1—N1—C2 | 109.91 (10) | N1i—C1—H1 | 109.3 (5) |
C1—N1—H1' | 100.8 (18) | N1—C1—H1 | 109.3 (5) |
C2—N1—H1' | 106.0 (18) | C1ii—C1—H1 | 108.9 (10) |
C1—N1—H1'' | 104.5 (14) | N1—C2—C2iii | 111.18 (9) |
C2—N1—H1'' | 104.1 (14) | N1—C2—H2A | 110.3 (9) |
H1'—N1—H1'' | 131 (3) | C2iii—C2—H2A | 108.8 (11) |
N1i—C1—N1 | 108.77 (13) | N1—C2—H2B | 108.3 (9) |
N1i—C1—C1ii | 110.26 (10) | C2iii—C2—H2B | 112.2 (8) |
N1—C1—C1ii | 110.25 (10) | H2A—C2—H2B | 105.9 (13) |
| | | |
C2—N1—C1—N1i | 179.27 (7) | C1—N1—C2—C2iii | −56.40 (18) |
C2—N1—C1—C1ii | 58.26 (19) | | |
Symmetry codes: (i) x, −y+1, z; (ii) −x, −y+1, −z+1; (iii) −x, y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1′···N1iv | 0.80 (4) | 2.36 (4) | 3.146 (3) | 167 (3) |
N1—H1′′···N1v | 0.93 (3) | 2.27 (3) | 3.182 (3) | 168 (2) |
Symmetry codes: (iv) −x+1, y, −z+2; (v) −x, y, −z+2. |
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