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The molecule of the title compound, C14H18N6, lies on a crystallographic centre of inversion. The unique C-N-N and N-N-N angles are 115.8 (3) and 173.3 (4)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028091/lh2144sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028091/lh2144Isup2.hkl
Contains datablock I

CCDC reference: 618287

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.182
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.790 0.990 Tmin(prime) and Tmax expected: 0.979 0.987 RR(prime) = 0.804 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.80 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1,6-Diazidodiamantane top
Crystal data top
C14H18N6Z = 1
Mr = 270.33F(000) = 144
Triclinic, P1Dx = 1.456 Mg m3
Hall symbol: -P 1Melting point: 362 K
a = 6.574 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.036 (9) ÅCell parameters from 480 reflections
c = 7.478 (10) Åθ = 3.0–25.8°
α = 76.36 (2)°µ = 0.09 mm1
β = 67.78 (2)°T = 294 K
γ = 77.75 (2)°Block, colourless
V = 308.3 (7) Å30.22 × 0.16 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1084 independent reflections
Radiation source: fine-focus sealed tube633 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 77
Tmin = 0.790, Tmax = 0.990k = 86
1555 measured reflectionsl = 86
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0886P)2 + 0.0788P]
where P = (Fo2 + 2Fc2)/3
1084 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 1.44 (s, 2H), 1.48 (s, 2H), 1.83–1.84 (m, 4H), 1.91 (s, 4H), 2.09–2.12 (m, 6H);

13C NMR (75 MHz, CDCl3, δ, p.p.m.): 285.08, 31.95, 41.48, 41.62, 62.50.

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
xyzUiso*/Ueq
N10.2562 (4)0.1679 (4)0.2526 (4)0.0526 (8)
N20.2409 (4)0.3394 (5)0.1794 (4)0.0539 (8)
N30.2209 (7)0.4919 (6)0.0994 (5)0.0939 (13)
C10.3438 (4)0.1177 (4)0.4136 (4)0.0367 (7)
C20.3428 (4)0.1005 (4)0.4827 (4)0.0383 (8)
H20.19070.13010.52500.046*
C30.4895 (5)0.2126 (5)0.3193 (4)0.0463 (8)
H3A0.48650.35320.36520.056*
H3B0.43560.17410.21000.056*
C40.7255 (5)0.0489 (5)0.1835 (4)0.0488 (9)
H4A0.87620.07760.14210.059*
H4B0.67590.09030.07170.059*
C50.5779 (4)0.1592 (4)0.3446 (4)0.0388 (8)
H50.58110.30110.29630.047*
C60.1982 (5)0.2285 (5)0.5766 (4)0.0484 (8)
H6A0.19890.36930.52990.058*
H6B0.04690.20120.61870.058*
C70.2802 (5)0.1677 (5)0.7452 (4)0.0463 (8)
H70.18420.24010.85110.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0645 (18)0.0541 (19)0.0503 (16)0.0050 (13)0.0358 (14)0.0058 (14)
N20.0641 (19)0.055 (2)0.0446 (16)0.0088 (15)0.0284 (14)0.0112 (15)
N30.141 (4)0.063 (3)0.081 (2)0.015 (2)0.065 (2)0.001 (2)
C10.0383 (15)0.0437 (18)0.0322 (15)0.0058 (13)0.0162 (13)0.0070 (12)
C20.0387 (16)0.0435 (19)0.0369 (16)0.0142 (13)0.0142 (13)0.0054 (13)
C30.062 (2)0.0435 (19)0.0415 (17)0.0104 (15)0.0230 (15)0.0115 (14)
C40.0473 (17)0.065 (2)0.0288 (15)0.0141 (15)0.0049 (14)0.0067 (14)
C50.0470 (17)0.0375 (17)0.0321 (15)0.0134 (13)0.0126 (13)0.0014 (12)
C60.0493 (18)0.049 (2)0.0466 (19)0.0027 (14)0.0167 (15)0.0150 (15)
C70.0485 (17)0.055 (2)0.0320 (15)0.0008 (14)0.0069 (13)0.0197 (14)
Geometric parameters (Å, º) top
N1—N21.202 (4)C3—H3B0.9700
N1—C11.464 (4)C4—C51.494 (4)
N2—N31.106 (4)C4—C7i1.495 (4)
C1—C51.497 (4)C4—H4A0.9700
C1—C21.501 (4)C4—H4B0.9700
C1—C61.503 (4)C5—H50.9800
C2—C5i1.509 (4)C6—C71.492 (4)
C2—C31.512 (4)C6—H6A0.9700
C2—H20.9800C6—H6B0.9700
C3—C7i1.484 (4)C7—H70.9800
C3—H3A0.9700
N2—N1—C1115.8 (3)C7i—C4—H4A109.8
N3—N2—N1173.3 (4)C5—C4—H4B109.8
N1—C1—C5111.3 (2)C7i—C4—H4B109.8
N1—C1—C2106.0 (2)H4A—C4—H4B108.2
C5—C1—C2108.3 (2)C4—C5—C1111.4 (2)
N1—C1—C6110.1 (3)C4—C5—C2i110.3 (3)
C5—C1—C6110.7 (2)C1—C5—C2i108.1 (2)
C2—C1—C6110.4 (2)C4—C5—H5109.0
C1—C2—C5i108.3 (2)C1—C5—H5109.0
C1—C2—C3110.6 (2)C2i—C5—H5109.0
C5i—C2—C3110.9 (3)C7—C6—C1109.9 (3)
C1—C2—H2109.0C7—C6—H6A109.7
C5i—C2—H2109.0C1—C6—H6A109.7
C3—C2—H2109.0C7—C6—H6B109.7
C7i—C3—C2109.1 (2)C1—C6—H6B109.7
C7i—C3—H3A109.9H6A—C6—H6B108.2
C2—C3—H3A109.9C3i—C7—C6109.5 (3)
C7i—C3—H3B109.9C3i—C7—C4i110.1 (3)
C2—C3—H3B109.9C6—C7—C4i108.8 (3)
H3A—C3—H3B108.3C3i—C7—H7109.5
C5—C4—C7i109.5 (2)C6—C7—H7109.5
C5—C4—H4A109.8C4i—C7—H7109.5
N2—N1—C1—C563.7 (3)C7i—C4—C5—C2i61.0 (3)
N2—N1—C1—C2178.8 (2)N1—C1—C5—C457.6 (3)
N2—N1—C1—C659.4 (4)C2—C1—C5—C458.4 (3)
N1—C1—C2—C5i177.5 (2)C6—C1—C5—C4179.6 (2)
C5—C1—C2—C5i63.0 (3)N1—C1—C5—C2i179.0 (2)
C6—C1—C2—C5i58.2 (3)C2—C1—C5—C2i62.9 (3)
N1—C1—C2—C360.9 (3)C6—C1—C5—C2i58.2 (3)
C5—C1—C2—C358.6 (3)N1—C1—C6—C7176.6 (2)
C6—C1—C2—C3179.9 (2)C5—C1—C6—C759.9 (3)
C1—C2—C3—C7i60.0 (3)C2—C1—C6—C759.9 (3)
C5i—C2—C3—C7i60.0 (3)C1—C6—C7—C3i60.2 (3)
C7i—C4—C5—C159.0 (3)C1—C6—C7—C4i60.1 (3)
Symmetry code: (i) x+1, y, z+1.
 

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