1,3-Phenyl-enediammonium dinitrate.

In the title compound, C(6)H(10)N(2) (2+)·2NO(3) (-), the dication lies on a crystallographic twofold rotation axis. The nitrate ions are linked to the dications though N-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For general background to polyamines, see: Bianchi et al. (1997 ▶); Ilioudis et al. (2002 ▶); Hossain (2008 ▶). For related structures, see: Anderson et al. (2006 ▶; Gawlicka-Chruszcz & Stadnicka (2002 ▶); Soumhi & Jouini (1995 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

C6H10N2 2+·2NO3 −

M = 234.18

Monoclinic,

a = 16.2548 (12) Å

b = 9.6212 (8) Å

c = 7.1070 (6) Å

β = 115.506 (6)°

V = 1003.14 (14) Å3

Z = 4

Cu Kα radiation

μ = 1.22 mm−1

T = 100 K

0.53 × 0.50 × 0.24 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.562, T max = 0.761

5278 measured reflections

942 independent reflections

882 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.01

942 reflections

84 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039166/ci2920sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039166/ci2920Isup2.hkl

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

C6H10N22+·2NO3−	F(000) = 488
Mr = 234.18	Dx = 1.551 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 3468 reflections
a = 16.2548 (12) Å	θ = 5.5–69.5°
b = 9.6212 (8) Å	µ = 1.22 mm−1
c = 7.1070 (6) Å	T = 100 K
β = 115.506 (6)°	Block, colorless
V = 1003.14 (14) Å3	0.53 × 0.50 × 0.24 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	942 independent reflections
Radiation source: fine-focus sealed tube	882 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 69.5°, θmin = 5.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −19→18
Tmin = 0.562, Tmax = 0.761	k = −11→11
5278 measured reflections	l = −8→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.054P)2 + 1.07P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
942 reflections	Δρmax = 0.26 e Å−3
84 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (5)

	x	y	z	Uiso*/Ueq
N1A	0.16571 (7)	0.19642 (12)	1.08086 (17)	0.0129 (3)
O1A	0.11343 (7)	0.11334 (11)	0.94063 (14)	0.0171 (3)
O2A	0.17425 (7)	0.31761 (10)	1.03487 (16)	0.0205 (3)
O3A	0.20794 (7)	0.15171 (11)	1.26369 (14)	0.0170 (3)
C1	0.0000	0.16909 (19)	0.2500	0.0119 (4)
H1	0.0000	0.0703	0.2500	0.014*
C2	0.06684 (9)	0.24329 (14)	0.40956 (19)	0.0125 (3)
C3	0.06855 (9)	0.38745 (15)	0.4119 (2)	0.0148 (3)
H3	0.1156	0.4364	0.5218	0.018*
C4	0.0000	0.4588 (2)	0.2500	0.0167 (4)
H4	0.0000	0.5575	0.2500	0.020*
N5	0.13746 (8)	0.16679 (12)	0.58086 (17)	0.0136 (3)
H5A	0.1261 (12)	0.1620 (17)	0.700 (3)	0.016*
H5B	0.1409 (11)	0.079 (2)	0.535 (3)	0.016*
H5C	0.1918 (13)	0.2147 (19)	0.624 (3)	0.016*

	U11	U22	U33	U12	U13	U23
N1A	0.0125 (6)	0.0140 (6)	0.0121 (6)	0.0001 (4)	0.0053 (4)	−0.0013 (4)
O1A	0.0187 (5)	0.0179 (5)	0.0115 (5)	−0.0058 (4)	0.0034 (4)	−0.0038 (4)
O2A	0.0234 (6)	0.0108 (5)	0.0243 (6)	−0.0001 (4)	0.0075 (4)	0.0016 (4)
O3A	0.0154 (5)	0.0232 (6)	0.0100 (5)	−0.0005 (4)	0.0032 (4)	0.0017 (4)
C1	0.0139 (9)	0.0107 (9)	0.0117 (9)	0.000	0.0062 (7)	0.000
C2	0.0122 (7)	0.0161 (7)	0.0097 (6)	0.0005 (5)	0.0053 (5)	0.0011 (5)
C3	0.0157 (7)	0.0151 (7)	0.0138 (7)	−0.0031 (5)	0.0065 (6)	−0.0034 (5)
C4	0.0215 (10)	0.0119 (9)	0.0191 (9)	0.000	0.0112 (8)	0.000
N5	0.0133 (6)	0.0149 (6)	0.0098 (6)	−0.0005 (4)	0.0022 (5)	−0.0005 (4)

N1A—O2A	1.2348 (16)	C3—C4	1.3901 (16)
N1A—O3A	1.2556 (15)	C3—H3	0.95
N1A—O1A	1.2747 (15)	C4—H4	0.95
C1—C2	1.3838 (16)	N5—H5A	0.943 (19)
C1—H1	0.95	N5—H5B	0.92 (2)
C2—C3	1.387 (2)	N5—H5C	0.924 (19)
C2—N5	1.4621 (16)
O2A—N1A—O3A	121.59 (11)	C4—C3—H3	120.7
O2A—N1A—O1A	119.88 (11)	C3i—C4—C3	120.83 (18)
O3A—N1A—O1A	118.53 (11)	C3—C4—H4	119.6
C2i—C1—C2	117.89 (17)	C2—N5—H5A	112.7 (10)
C2—C1—H1	121.1	C2—N5—H5B	108.4 (11)
C1—C2—C3	122.02 (12)	H5A—N5—H5B	109.8 (14)
C1—C2—N5	118.72 (13)	C2—N5—H5C	108.7 (11)
C3—C2—N5	119.26 (11)	H5A—N5—H5C	104.8 (15)
C2—C3—C4	118.62 (12)	H5B—N5—H5C	112.5 (15)
C2—C3—H3	120.7
C2i—C1—C2—C3	−0.49 (9)	N5—C2—C3—C4	−178.80 (10)
C2i—C1—C2—N5	179.28 (13)	C2—C3—C4—C3i	−0.47 (8)
C1—C2—C3—C4	0.97 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O1A	0.94 (2)	1.87 (2)	2.7955 (15)	168 (2)
N5—H5B···O1Aii	0.92 (2)	1.95 (2)	2.8416 (16)	163 (2)
N5—H5C···O3Aiii	0.92 (2)	1.96 (2)	2.8626 (16)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O1A	0.94 (2)	1.87 (2)	2.7955 (15)	168 (2)
N5—H5B⋯O1Ai	0.92 (2)	1.95 (2)	2.8416 (16)	163 (2)
N5—H5C⋯O3Aii	0.92 (2)	1.96 (2)	2.8626 (16)	167 (2)

Symmetry codes: (i) ; (ii) .