Decane-1,10-diaminium dinitrate.

The crystal structure of the title compound, C(10)H(26)N(2) (2+)·2NO(3) (-), exhibits a back-to-back paired double-stacked packing arrangement culminating in an overall double zigzag pattern of the dications. Each pair of double-stacked dications is surrounded by a ring of ten nitrate anions. An intricate three-dimensional N---H...O and N---H...(O,O) hydrogen-bonding network exists in the crystal structure.

Related literature

For related structural studies of n-alkyl-diammonium nitrate salts, see: van Blerk & Kruger (2009 ▶). The structures of many other related n-alkyl­diammonium salts are available in the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C10H26N2 2+·2NO3 −

M = 298.35

Monoclinic,

a = 5.4066 (5) Å

b = 20.3556 (16) Å

c = 14.5567 (11) Å

β = 93.853 (5)°

V = 1598.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.38 × 0.14 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (AXScale; Bruker, 2008 ▶) T min = 0.963, T max = 0.987

36629 measured reflections

3857 independent reflections

1797 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.157

S = 1.02

3857 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART-NT (Bruker, 1999 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶ ) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042929/lr2031sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042929/lr2031Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042929/lr2031Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811042929/lr2031Isup4.cml

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

C10H26N22+·2NO3−	F(000) = 648
Mr = 298.35	Dx = 1.240 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1797 reflections
a = 5.4066 (5) Å	θ = 1.7–28.0°
b = 20.3556 (16) Å	µ = 0.10 mm−1
c = 14.5567 (11) Å	T = 295 K
β = 93.853 (5)°	Rectangular, colourless
V = 1598.4 (2) Å3	0.38 × 0.14 × 0.13 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3857 independent reflections
Radiation source: fine-focus sealed tube	1797 reflections with I > 2σ(I)
graphite	Rint = 0.086
φ and ω scans	θmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan (AXScale; Bruker, 2008)	h = −7→7
Tmin = 0.963, Tmax = 0.987	k = −26→26
36629 measured reflections	l = −19→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0428P)2 + 1.010P] where P = (Fo2 + 2Fc2)/3
3857 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.16 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	−0.3760 (5)	0.44497 (14)	0.84533 (18)	0.0520 (7)
H1A	−0.4514	0.4872	0.8567	0.062*
H1B	−0.4922	0.4196	0.8060	0.062*
C2	−0.1406 (5)	0.45547 (13)	0.79673 (18)	0.0507 (7)
H2A	−0.0804	0.4133	0.7766	0.061*
H2B	−0.0150	0.4740	0.8399	0.061*
C3	−0.1773 (5)	0.50071 (13)	0.71403 (17)	0.0481 (7)
H3A	−0.2560	0.5409	0.7327	0.058*
H3B	−0.2879	0.4797	0.6677	0.058*
C4	0.0648 (5)	0.51777 (13)	0.67177 (18)	0.0482 (7)
H4A	0.1809	0.5345	0.7198	0.058*
H4B	0.1349	0.4779	0.6479	0.058*
C5	0.0380 (5)	0.56815 (12)	0.59469 (17)	0.0429 (6)
H5A	−0.0758	0.5511	0.5461	0.051*
H5B	−0.0348	0.6078	0.6182	0.051*
C6	0.2797 (5)	0.58597 (12)	0.55382 (17)	0.0440 (6)
H6A	0.3980	0.5997	0.6031	0.053*
H6B	0.3459	0.5471	0.5258	0.053*
C7	0.2555 (5)	0.63977 (12)	0.48257 (17)	0.0453 (6)
H7A	0.1883	0.6786	0.5106	0.054*
H7B	0.1376	0.6259	0.4332	0.054*
C8	0.4976 (5)	0.65833 (12)	0.44129 (18)	0.0451 (6)
H8A	0.6183	0.6706	0.4907	0.054*
H8B	0.5613	0.6202	0.4106	0.054*
C9	0.4698 (5)	0.71431 (13)	0.3732 (2)	0.0534 (7)
H9A	0.3583	0.7009	0.3217	0.064*
H9B	0.3950	0.7514	0.4026	0.064*
C10	0.7120 (5)	0.73582 (13)	0.33742 (19)	0.0521 (7)
H10A	0.8249	0.7489	0.3888	0.063*
H10B	0.7860	0.6991	0.3069	0.063*
N1	−0.3260 (4)	0.40998 (11)	0.93400 (14)	0.0574 (6)
H1C	−0.2968	0.3678	0.9231	0.086*
H1D	−0.4570	0.4135	0.9676	0.086*
H1E	−0.1942	0.4277	0.9645	0.086*
N2	0.6789 (4)	0.79153 (10)	0.27172 (15)	0.0535 (6)
H2C	0.5709	0.7802	0.2256	0.080*
H2D	0.8238	0.8014	0.2496	0.080*
H2E	0.6220	0.8263	0.3007	0.080*
N3	0.6591 (5)	0.75622 (13)	0.64512 (16)	0.0567 (6)
N4	0.3114 (5)	0.89735 (12)	0.42210 (17)	0.0569 (6)
O1	0.6423 (4)	0.70426 (10)	0.68968 (14)	0.0644 (6)
O2	0.4762 (4)	0.79050 (12)	0.62569 (18)	0.0889 (8)
O3	0.8667 (4)	0.77376 (11)	0.62153 (16)	0.0784 (7)
O4	0.2928 (4)	0.93497 (10)	0.49020 (14)	0.0663 (6)
O5	0.1263 (5)	0.86953 (13)	0.38802 (17)	0.0916 (8)
O6	0.5185 (4)	0.89060 (11)	0.39132 (14)	0.0746 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0506 (17)	0.0611 (18)	0.0445 (15)	−0.0043 (13)	0.0048 (13)	0.0081 (13)
C2	0.0479 (17)	0.0566 (17)	0.0484 (15)	0.0036 (13)	0.0100 (13)	0.0087 (13)
C3	0.0459 (16)	0.0545 (16)	0.0442 (15)	0.0002 (13)	0.0044 (13)	0.0069 (13)
C4	0.0461 (16)	0.0532 (16)	0.0456 (15)	0.0036 (13)	0.0058 (13)	0.0066 (13)
C5	0.0422 (15)	0.0450 (14)	0.0414 (14)	0.0023 (12)	0.0027 (12)	0.0027 (11)
C6	0.0405 (15)	0.0442 (14)	0.0471 (15)	0.0007 (12)	0.0019 (12)	0.0043 (12)
C7	0.0430 (15)	0.0467 (15)	0.0463 (15)	0.0000 (12)	0.0048 (12)	0.0061 (12)
C8	0.0397 (15)	0.0482 (15)	0.0474 (15)	0.0021 (12)	0.0036 (12)	0.0070 (12)
C9	0.0429 (16)	0.0566 (17)	0.0611 (17)	0.0013 (13)	0.0065 (13)	0.0145 (14)
C10	0.0439 (16)	0.0526 (16)	0.0607 (17)	0.0031 (13)	0.0091 (14)	0.0117 (14)
N1	0.0617 (16)	0.0646 (15)	0.0476 (13)	0.0005 (12)	0.0160 (12)	0.0069 (12)
N2	0.0491 (14)	0.0523 (13)	0.0601 (14)	−0.0028 (11)	0.0109 (11)	0.0125 (11)
N3	0.0550 (17)	0.0659 (17)	0.0497 (14)	−0.0067 (14)	0.0067 (12)	−0.0110 (13)
N4	0.0588 (17)	0.0538 (15)	0.0593 (16)	0.0073 (13)	0.0115 (14)	−0.0001 (13)
O1	0.0645 (14)	0.0636 (13)	0.0666 (13)	−0.0052 (10)	0.0152 (11)	0.0005 (11)
O2	0.0615 (15)	0.0870 (17)	0.118 (2)	0.0084 (13)	0.0017 (14)	0.0138 (15)
O3	0.0573 (14)	0.0883 (16)	0.0919 (17)	−0.0133 (11)	0.0215 (12)	0.0101 (13)
O4	0.0644 (14)	0.0747 (14)	0.0612 (13)	0.0008 (11)	0.0147 (11)	−0.0154 (11)
O5	0.0677 (16)	0.0986 (18)	0.108 (2)	−0.0141 (14)	0.0001 (14)	−0.0358 (15)
O6	0.0610 (14)	0.0887 (16)	0.0768 (14)	0.0138 (12)	0.0241 (12)	−0.0092 (12)

C1—N1	1.483 (3)	C8—C9	1.511 (3)
C1—C2	1.512 (3)	C8—H8A	0.9700
C1—H1A	0.9700	C8—H8B	0.9700
C1—H1B	0.9700	C9—C10	1.507 (3)
C2—C3	1.518 (3)	C9—H9A	0.9700
C2—H2A	0.9700	C9—H9B	0.9700
C2—H2B	0.9700	C10—N2	1.487 (3)
C3—C4	1.523 (3)	C10—H10A	0.9700
C3—H3A	0.9700	C10—H10B	0.9700
C3—H3B	0.9700	N1—H1C	0.8900
C4—C5	1.520 (3)	N1—H1D	0.8900
C4—H4A	0.9700	N1—H1E	0.8900
C4—H4B	0.9700	N2—H2C	0.8900
C5—C6	1.516 (3)	N2—H2D	0.8900
C5—H5A	0.9700	N2—H2E	0.8900
C5—H5B	0.9700	N3—O2	1.228 (3)
C6—C7	1.508 (3)	N3—O1	1.247 (3)
C6—H6A	0.9700	N3—O3	1.248 (3)
C6—H6B	0.9700	N4—O5	1.225 (3)
C7—C8	1.524 (3)	N4—O6	1.241 (3)
C7—H7A	0.9700	N4—O4	1.262 (3)
C7—H7B	0.9700
N1—C1—C2	111.4 (2)	C6—C7—H7B	108.6
N1—C1—H1A	109.3	C8—C7—H7B	108.6
C2—C1—H1A	109.3	H7A—C7—H7B	107.6
N1—C1—H1B	109.3	C9—C8—C7	113.3 (2)
C2—C1—H1B	109.3	C9—C8—H8A	108.9
H1A—C1—H1B	108.0	C7—C8—H8A	108.9
C1—C2—C3	112.8 (2)	C9—C8—H8B	108.9
C1—C2—H2A	109.0	C7—C8—H8B	108.9
C3—C2—H2A	109.0	H8A—C8—H8B	107.7
C1—C2—H2B	109.0	C10—C9—C8	113.3 (2)
C3—C2—H2B	109.0	C10—C9—H9A	108.9
H2A—C2—H2B	107.8	C8—C9—H9A	108.9
C2—C3—C4	112.8 (2)	C10—C9—H9B	108.9
C2—C3—H3A	109.0	C8—C9—H9B	108.9
C4—C3—H3A	109.0	H9A—C9—H9B	107.7
C2—C3—H3B	109.0	N2—C10—C9	112.0 (2)
C4—C3—H3B	109.0	N2—C10—H10A	109.2
H3A—C3—H3B	107.8	C9—C10—H10A	109.2
C5—C4—C3	114.2 (2)	N2—C10—H10B	109.2
C5—C4—H4A	108.7	C9—C10—H10B	109.2
C3—C4—H4A	108.7	H10A—C10—H10B	107.9
C5—C4—H4B	108.7	C1—N1—H1C	109.5
C3—C4—H4B	108.7	C1—N1—H1D	109.5
H4A—C4—H4B	107.6	H1C—N1—H1D	109.5
C6—C5—C4	114.2 (2)	C1—N1—H1E	109.5
C6—C5—H5A	108.7	H1C—N1—H1E	109.5
C4—C5—H5A	108.7	H1D—N1—H1E	109.5
C6—C5—H5B	108.7	C10—N2—H2C	109.5
C4—C5—H5B	108.7	C10—N2—H2D	109.5
H5A—C5—H5B	107.6	H2C—N2—H2D	109.5
C7—C6—C5	114.0 (2)	C10—N2—H2E	109.5
C7—C6—H6A	108.8	H2C—N2—H2E	109.5
C5—C6—H6A	108.8	H2D—N2—H2E	109.5
C7—C6—H6B	108.8	O2—N3—O1	121.1 (3)
C5—C6—H6B	108.8	O2—N3—O3	120.0 (3)
H6A—C6—H6B	107.7	O1—N3—O3	118.9 (3)
C6—C7—C8	114.5 (2)	O5—N4—O6	122.3 (3)
C6—C7—H7A	108.6	O5—N4—O4	119.5 (2)
C8—C7—H7A	108.6	O6—N4—O4	118.2 (3)
N1—C1—C2—C3	−170.5 (2)	C5—C6—C7—C8	179.7 (2)
C1—C2—C3—C4	173.2 (2)	C6—C7—C8—C9	−177.5 (2)
C2—C3—C4—C5	−174.4 (2)	C7—C8—C9—C10	176.0 (2)
C3—C4—C5—C6	179.0 (2)	C8—C9—C10—N2	−179.2 (2)
C4—C5—C6—C7	−175.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2i	0.89	2.48	3.235 (3)	143
N1—H1C···O3i	0.89	2.05	2.892 (3)	158
N1—H1E···O4i	0.89	2.23	3.059 (3)	155
N1—H1E···O6i	0.89	2.37	2.969 (3)	125
N1—H1D···O4ii	0.89	2.00	2.867 (3)	163
N1—H1D···O5ii	0.89	2.51	3.255 (3)	141
N2—H2C···O1iii	0.89	2.36	3.063 (3)	136
N2—H2C···O3iii	0.89	2.12	2.983 (3)	163
N2—H2D···O1iv	0.89	1.99	2.849 (3)	163
N2—H2E···O6	0.89	1.97	2.838 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O2i	0.89	2.48	3.235 (3)	143
N1—H1C⋯O3i	0.89	2.05	2.892 (3)	158
N1—H1E⋯O4i	0.89	2.23	3.059 (3)	155
N1—H1E⋯O6i	0.89	2.37	2.969 (3)	125
N1—H1D⋯O4ii	0.89	2.00	2.867 (3)	163
N1—H1D⋯O5ii	0.89	2.51	3.255 (3)	141
N2—H2C⋯O1iii	0.89	2.36	3.063 (3)	136
N2—H2C⋯O3iii	0.89	2.12	2.983 (3)	163
N2—H2D⋯O1iv	0.89	1.99	2.849 (3)	163
N2—H2E⋯O6	0.89	1.97	2.838 (3)	166

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .