1,6-Diazido­diamantane

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.

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

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Computing details

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

Crystal data

C14H18N6	Z = 1
Mr = 270.33	F(000) = 144
Triclinic, P1	Dx = 1.456 Mg m^−3
Hall symbol: -P 1	Melting point: 362 K
a = 6.574 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.036 (9) Å	Cell parameters from 480 reflections
c = 7.478 (10) Å	θ = 3.0–25.8°
α = 76.36 (2)°	µ = 0.09 mm^−1
β = 67.78 (2)°	T = 294 K
γ = 77.75 (2)°	Block, colourless
V = 308.3 (7) Å^3	0.22 × 0.16 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1084 independent reflections
Radiation source: fine-focus sealed tube	633 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→7
Tmin = 0.790, Tmax = 0.990	k = −8→6
1555 measured reflections	l = −8→6

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0886P)^2 + 0.0788P] where P = (Fo^2 + 2Fc^2)/3
1084 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2562 (4)	0.1679 (4)	0.2526 (4)	0.0526 (8)
N2	0.2409 (4)	0.3394 (5)	0.1794 (4)	0.0539 (8)
N3	0.2209 (7)	0.4919 (6)	0.0994 (5)	0.0939 (13)
C1	0.3438 (4)	0.1177 (4)	0.4136 (4)	0.0367 (7)
C2	0.3428 (4)	−0.1005 (4)	0.4827 (4)	0.0383 (8)
H2	0.1907	−0.1301	0.5250	0.046*
C3	0.4895 (5)	−0.2126 (5)	0.3193 (4)	0.0463 (8)
H3A	0.4865	−0.3532	0.3652	0.056*
H3B	0.4356	−0.1741	0.2100	0.056*
C4	0.7255 (5)	0.0489 (5)	0.1835 (4)	0.0488 (9)
H4A	0.8762	0.0776	0.1421	0.059*
H4B	0.6759	0.0903	0.0717	0.059*
C5	0.5779 (4)	0.1592 (4)	0.3446 (4)	0.0388 (8)
H5	0.5811	0.3011	0.2963	0.047*
C6	0.1982 (5)	0.2285 (5)	0.5766 (4)	0.0484 (8)
H6A	0.1989	0.3693	0.5299	0.058*
H6B	0.0469	0.2012	0.6187	0.058*
C7	0.2802 (5)	0.1677 (5)	0.7452 (4)	0.0463 (8)
H7	0.1842	0.2401	0.8511	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0645 (18)	0.0541 (19)	0.0503 (16)	−0.0050 (13)	−0.0358 (14)	−0.0058 (14)
N2	0.0641 (19)	0.055 (2)	0.0446 (16)	0.0088 (15)	−0.0284 (14)	−0.0112 (15)
N3	0.141 (4)	0.063 (3)	0.081 (2)	0.015 (2)	−0.065 (2)	0.001 (2)
C1	0.0383 (15)	0.0437 (18)	0.0322 (15)	−0.0058 (13)	−0.0162 (13)	−0.0070 (12)
C2	0.0387 (16)	0.0435 (19)	0.0369 (16)	−0.0142 (13)	−0.0142 (13)	−0.0054 (13)
C3	0.062 (2)	0.0435 (19)	0.0415 (17)	−0.0104 (15)	−0.0230 (15)	−0.0115 (14)
C4	0.0473 (17)	0.065 (2)	0.0288 (15)	−0.0141 (15)	−0.0049 (14)	−0.0067 (14)
C5	0.0470 (17)	0.0375 (17)	0.0321 (15)	−0.0134 (13)	−0.0126 (13)	−0.0014 (12)
C6	0.0493 (18)	0.049 (2)	0.0466 (19)	0.0027 (14)	−0.0167 (15)	−0.0150 (15)
C7	0.0485 (17)	0.055 (2)	0.0320 (15)	0.0008 (14)	−0.0069 (13)	−0.0197 (14)

Geometric parameters (Å, º)

N1—N2	1.202 (4)	C3—H3B	0.9700
N1—C1	1.464 (4)	C4—C5	1.494 (4)
N2—N3	1.106 (4)	C4—C7^i	1.495 (4)
C1—C5	1.497 (4)	C4—H4A	0.9700
C1—C2	1.501 (4)	C4—H4B	0.9700
C1—C6	1.503 (4)	C5—H5	0.9800
C2—C5^i	1.509 (4)	C6—C7	1.492 (4)
C2—C3	1.512 (4)	C6—H6A	0.9700
C2—H2	0.9800	C6—H6B	0.9700
C3—C7^i	1.484 (4)	C7—H7	0.9800
C3—H3A	0.9700
N2—N1—C1	115.8 (3)	C7^i—C4—H4A	109.8
N3—N2—N1	173.3 (4)	C5—C4—H4B	109.8
N1—C1—C5	111.3 (2)	C7^i—C4—H4B	109.8
N1—C1—C2	106.0 (2)	H4A—C4—H4B	108.2
C5—C1—C2	108.3 (2)	C4—C5—C1	111.4 (2)
N1—C1—C6	110.1 (3)	C4—C5—C2^i	110.3 (3)
C5—C1—C6	110.7 (2)	C1—C5—C2^i	108.1 (2)
C2—C1—C6	110.4 (2)	C4—C5—H5	109.0
C1—C2—C5^i	108.3 (2)	C1—C5—H5	109.0
C1—C2—C3	110.6 (2)	C2^i—C5—H5	109.0
C5^i—C2—C3	110.9 (3)	C7—C6—C1	109.9 (3)
C1—C2—H2	109.0	C7—C6—H6A	109.7
C5^i—C2—H2	109.0	C1—C6—H6A	109.7
C3—C2—H2	109.0	C7—C6—H6B	109.7
C7^i—C3—C2	109.1 (2)	C1—C6—H6B	109.7
C7^i—C3—H3A	109.9	H6A—C6—H6B	108.2
C2—C3—H3A	109.9	C3^i—C7—C6	109.5 (3)
C7^i—C3—H3B	109.9	C3^i—C7—C4^i	110.1 (3)
C2—C3—H3B	109.9	C6—C7—C4^i	108.8 (3)
H3A—C3—H3B	108.3	C3^i—C7—H7	109.5
C5—C4—C7^i	109.5 (2)	C6—C7—H7	109.5
C5—C4—H4A	109.8	C4^i—C7—H7	109.5
N2—N1—C1—C5	−63.7 (3)	C7^i—C4—C5—C2^i	61.0 (3)
N2—N1—C1—C2	178.8 (2)	N1—C1—C5—C4	−57.6 (3)
N2—N1—C1—C6	59.4 (4)	C2—C1—C5—C4	58.4 (3)
N1—C1—C2—C5^i	−177.5 (2)	C6—C1—C5—C4	179.6 (2)
C5—C1—C2—C5^i	63.0 (3)	N1—C1—C5—C2^i	−179.0 (2)
C6—C1—C2—C5^i	−58.2 (3)	C2—C1—C5—C2^i	−62.9 (3)
N1—C1—C2—C3	60.9 (3)	C6—C1—C5—C2^i	58.2 (3)
C5—C1—C2—C3	−58.6 (3)	N1—C1—C6—C7	176.6 (2)
C6—C1—C2—C3	−179.9 (2)	C5—C1—C6—C7	−59.9 (3)
C1—C2—C3—C7^i	60.0 (3)	C2—C1—C6—C7	59.9 (3)
C5^i—C2—C3—C7^i	−60.0 (3)	C1—C6—C7—C3^i	60.2 (3)
C7^i—C4—C5—C1	−59.0 (3)	C1—C6—C7—C4^i	−60.1 (3)

Symmetry code: (i) −x+1, −y, −z+1.