Hexane-1,6-diammonium dinitrate.

The hexane-1,6-diammonium cation of the title compound, C(6)H(18)N(2) (2+)·2NO(3) (-), lies across a crystallographic inversion centre and shows significant deviation from planarity in the hydro-carbon chain. This is evident from the torsion angle of -64.0°(2) along the N-C-C-C bond and thse torsion angle of -67.1°(2) along the C-C-C-C bonds. An intricate three-dimensional hydrogen-bonding network exists in the crystal structure, with each H atom on the ammonium group exhibiting bifurcated inter-actions to the nitrate anion. Complex hydrogen-bonded ring and chain motifs are also evident, in particular a 26-membered ring with graph-set notation R(4) (4)(26) is observed.

Related literature

For related structural studies of hexane-1,6-diammonium salts, see: van Blerk & Kruger (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C6H18N2 2+·2NO3 −

M = 242.24

Monoclinic,

a = 6.2947 (1) Å

b = 11.6783 (3) Å

c = 8.1211 (2) Å

β = 92.840 (1)°

V = 596.26 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.46 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (AX-Scale; Bruker, 2008 ▶) T min = 0.948, T max = 0.981

14665 measured reflections

1718 independent reflections

1107 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.147

S = 1.02

1718 reflections

74 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART-NT (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012963/fj2206sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012963/fj2206Isup2.hkl

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

C6H18N22+·2NO3−	F(000) = 260
Mr = 242.24	Dx = 1.349 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5933 reflections
a = 6.2947 (1) Å	θ = 2.5–25.2°
b = 11.6783 (3) Å	µ = 0.12 mm−1
c = 8.1211 (2) Å	T = 295 K
β = 92.840 (1)°	Rectangular, colourless
V = 596.26 (2) Å3	0.46 × 0.20 × 0.16 mm
Z = 2

Bruker SMART CCD diffractometer	1718 independent reflections
Radiation source: fine-focus sealed tube	1107 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 30.0°, θmin = 3.1°
Absorption correction: multi-scan (AX-Scale; Bruker, 2008)	h = −8→8
Tmin = 0.948, Tmax = 0.981	k = −16→16
14665 measured reflections	l = −11→11

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.1254P] where P = (Fo2 + 2Fc2)/3
1718 reflections	(Δ/σ)max < 0.001
74 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.19 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. 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
C1	0.7036 (3)	0.01369 (13)	0.31554 (19)	0.0599 (4)
H1A	0.5614	−0.0134	0.3351	0.072*
H1B	0.8020	−0.0243	0.3934	0.072*
C2	0.7584 (3)	−0.01708 (14)	0.1427 (2)	0.0593 (4)
H2A	0.7644	−0.0999	0.1351	0.071*
H2B	0.9000	0.0117	0.1251	0.071*
C3	0.6095 (2)	0.02648 (14)	0.00229 (18)	0.0540 (4)
H3A	0.5955	0.1088	0.0126	0.065*
H3B	0.6737	0.0110	−0.1016	0.065*
N1	0.7138 (2)	0.13945 (11)	0.34353 (15)	0.0544 (4)
H1C	0.6044	0.1730	0.2893	0.082*
H1D	0.8350	0.1667	0.3072	0.082*
H1E	0.7082	0.1539	0.4508	0.082*
N2	0.2075 (2)	0.23209 (11)	0.22415 (16)	0.0510 (3)
O1	0.03639 (19)	0.26482 (12)	0.15889 (16)	0.0710 (4)
O2	0.2102 (2)	0.15918 (11)	0.33405 (15)	0.0732 (4)
O3	0.3767 (2)	0.27276 (12)	0.17480 (16)	0.0714 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0791 (11)	0.0552 (9)	0.0448 (8)	0.0006 (8)	−0.0042 (7)	0.0031 (6)
C2	0.0622 (9)	0.0591 (9)	0.0559 (9)	0.0067 (7)	−0.0052 (7)	−0.0109 (7)
C3	0.0632 (9)	0.0583 (9)	0.0407 (7)	−0.0024 (7)	0.0046 (6)	−0.0062 (6)
N1	0.0544 (8)	0.0610 (8)	0.0479 (7)	−0.0035 (6)	0.0033 (6)	−0.0087 (5)
N2	0.0584 (8)	0.0501 (7)	0.0451 (7)	0.0059 (6)	0.0070 (6)	−0.0002 (5)
O1	0.0567 (7)	0.0808 (9)	0.0755 (9)	0.0130 (6)	0.0018 (6)	0.0188 (6)
O2	0.0782 (9)	0.0798 (8)	0.0615 (7)	0.0012 (7)	0.0045 (6)	0.0279 (6)
O3	0.0576 (8)	0.0846 (9)	0.0731 (8)	−0.0041 (6)	0.0131 (6)	0.0188 (6)

C1—N1	1.487 (2)	C3—H3A	0.9700
C1—C2	1.505 (2)	C3—H3B	0.9700
C1—H1A	0.9700	N1—H1C	0.8900
C1—H1B	0.9700	N1—H1D	0.8900
C2—C3	1.527 (2)	N1—H1E	0.8900
C2—H2A	0.9700	N2—O2	1.2330 (16)
C2—H2B	0.9700	N2—O1	1.2369 (17)
C3—C3i	1.510 (3)	N2—O3	1.2504 (17)
N1—C1—C2	111.60 (13)	C2—C3—H3A	108.7
N1—C1—H1A	109.3	C3i—C3—H3B	108.7
C2—C1—H1A	109.3	C2—C3—H3B	108.7
N1—C1—H1B	109.3	H3A—C3—H3B	107.6
C2—C1—H1B	109.3	C1—N1—H1C	109.5
H1A—C1—H1B	108.0	C1—N1—H1D	109.5
C1—C2—C3	117.17 (14)	H1C—N1—H1D	109.5
C1—C2—H2A	108.0	C1—N1—H1E	109.5
C3—C2—H2A	108.0	H1C—N1—H1E	109.5
C1—C2—H2B	108.0	H1D—N1—H1E	109.5
C3—C2—H2B	108.0	O2—N2—O1	120.27 (14)
H2A—C2—H2B	107.2	O2—N2—O3	120.85 (14)
C3i—C3—C2	114.07 (17)	O1—N2—O3	118.86 (13)
C3i—C3—H3A	108.7
N1—C1—C2—C3	−64.0 (2)	C1—C2—C3—C3i	−67.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2	0.89	2.53	3.1760 (19)	130
N1—H1C···O3	0.89	2.04	2.9184 (19)	171
N1—H1D···O1ii	0.89	2.13	2.9692 (18)	158
N1—H1D···O2ii	0.89	2.36	3.1374 (19)	146
N1—H1E···O1iii	0.89	2.26	3.0561 (18)	149
N1—H1E···O3iii	0.89	2.23	3.0110 (18)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O2	0.89	2.53	3.1760 (19)	130
N1—H1C⋯O3	0.89	2.04	2.9184 (19)	171
N1—H1D⋯O1ii	0.89	2.13	2.9692 (18)	158
N1—H1D⋯O2ii	0.89	2.36	3.1374 (19)	146
N1—H1E⋯O1iii	0.89	2.26	3.0561 (18)	149
N1—H1E⋯O3iii	0.89	2.23	3.0110 (18)	146

Symmetry codes: (ii) ; (iii) .