Butane-1,4-diammonium bis(perchlorate).

The butane-1,4-diammonium cation of the title compound, C(4)H(14)N(2) (2+)·2ClO(4) (-), lies on a special position of site symmetry 2/m, whereas the perchlorate anion is located on a crystallographic mirror plane. An intricate three-dimensional hydrogen-bonding network exists in the crystal structure with each H atom of the ammonium group exhibiting bifurcated inter-actions to the perchlorate anion. Complex hydrogen-bonded ring and chain motifs are also evident, in particular a 50-membered ring with graph-set notation R(10) (10)(50) is identified.

Related literature

For related structural studies of butane-1,4-diammonium salts, see: van Blerk & Kruger (2007 ▶); Lemmerer & Billing (2006 ▶); Gabro et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C4H14N2 2+·2ClO4 −

M = 289.07

Monoclinic,

a = 19.4755 (10) Å

b = 5.6210 (3) Å

c = 5.3470 (2) Å

β = 97.222 (3)°

V = 580.70 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.59 mm−1

T = 296 K

0.50 × 0.34 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (AX-Scale; Bruker, 2008 ▶) T min = 0.757, T max = 0.912

3067 measured reflections

793 independent reflections

694 reflections with I > 2s(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.155

S = 1.17

793 reflections

46 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); 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, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012025/bt5503sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012025/bt5503Isup2.hkl

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

C4H14N22+·2ClO4−	F(000) = 300
Mr = 289.07	Dx = 1.653 Mg m−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 1622 reflections
a = 19.4755 (10) Å	θ = 3.8–28.2°
b = 5.6210 (3) Å	µ = 0.59 mm−1
c = 5.3470 (2) Å	T = 296 K
β = 97.222 (3)°	Block, colourless
V = 580.70 (5) Å3	0.50 × 0.34 × 0.16 mm
Z = 2

Bruker APEXII CCD diffractometer	793 independent reflections
Radiation source: fine-focus sealed tube	694 reflections with I > 2s(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.3°, θmin = 3.8°
Absorption correction: multi-scan (AX-Scale; Bruker, 2008)	h = −23→25
Tmin = 0.757, Tmax = 0.912	k = −7→7
3067 measured reflections	l = −6→7

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0955P)2 + 0.3477P] where P = (Fo2 + 2Fc2)/3
793 reflections	(Δ/σ)max < 0.001
46 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.44 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	0.57860 (17)	0.0000	0.7538 (6)	0.0466 (8)
H1	0.5661	0.1394	0.8450	0.056*
C2	0.53822 (16)	0.0000	0.4976 (6)	0.0467 (8)
H2	0.5508	−0.1394	0.4065	0.056*
Cl1	0.65841 (4)	0.5000	0.27016 (13)	0.0403 (3)
N1	0.65459 (14)	0.0000	0.7476 (5)	0.0450 (7)
H1N	0.6762	0.0000	0.9045	0.068*
H2N	0.6666	0.1293	0.6673	0.068*
O1	0.69616 (13)	0.2898 (5)	0.2214 (5)	0.0755 (7)
O2	0.59205 (16)	0.5000	0.1238 (6)	0.0698 (9)
O3	0.65031 (17)	0.5000	0.5341 (5)	0.0633 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0461 (18)	0.061 (2)	0.0321 (15)	0.000	0.0021 (12)	0.000
C2	0.0403 (18)	0.068 (2)	0.0315 (15)	0.000	0.0028 (12)	0.000
Cl1	0.0480 (5)	0.0380 (5)	0.0344 (5)	0.000	0.0031 (3)	0.000
N1	0.0425 (15)	0.0501 (17)	0.0398 (14)	0.000	−0.0049 (11)	0.000
O1	0.0818 (14)	0.0697 (16)	0.0730 (14)	0.0253 (12)	0.0014 (11)	−0.0236 (11)
O2	0.0619 (18)	0.069 (2)	0.071 (2)	0.000	−0.0187 (14)	0.000
O3	0.095 (2)	0.0596 (17)	0.0377 (14)	0.000	0.0171 (13)	0.000

C1—N1	1.484 (4)	Cl1—O1	1.433 (2)
C1—C2	1.492 (4)	Cl1—O1ii	1.433 (2)
C1—H1	0.9700	Cl1—O3	1.440 (3)
C2—C2i	1.492 (6)	N1—H1N	0.8900
C2—H2	0.9700	N1—H2N	0.8900
Cl1—O2	1.424 (3)
N1—C1—C2	113.0 (3)	O2—Cl1—O1ii	110.54 (12)
N1—C1—H1	109.0	O1—Cl1—O1ii	111.1 (2)
C2—C1—H1	109.0	O2—Cl1—O3	109.6 (2)
H1—C1—H1iii	107.8	O1—Cl1—O3	107.48 (13)
C1—C2—C2i	113.3 (3)	O1ii—Cl1—O3	107.48 (13)
C1—C2—H2	108.9	C1—N1—H1N	109.5
C2i—C2—H2	108.9	C1—N1—H2N	109.5
H2—C2—H2iii	107.7	H1N—N1—H2N	109.5
O2—Cl1—O1	110.54 (12)
N1—C1—C2—C2i	180.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1iv	0.89	2.35	3.035 (3)	134
N1—H1N···O1v	0.89	2.35	3.035 (3)	134
N1—H2N···O1	0.89	2.68	3.435 (4)	143
N1—H2N···O3	0.89	2.21	3.0308 (14)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.89	2.35	3.035 (3)	134
N1—H1N⋯O1ii	0.89	2.35	3.035 (3)	134
N1—H2N⋯O1	0.89	2.68	3.435 (4)	143
N1—H2N⋯O3	0.89	2.21	3.0308 (14)	153

Symmetry codes: (i) ; (ii) .