Butane 1,4 di­ammonium bis­(perchlorate)

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(1)organic compounds Acta Crystallographica Section E. Data collection. Structure Reports Online. 3067 measured reflections 793 independent reflections 694 reflections with I > 2s(I) Rint = 0.028. Bruker APEXII CCD diffractometer Absorption correction: multi-scan (AX-Scale; Bruker, 2008) Tmin = 0.757, Tmax = 0.912. ISSN 1600-5368. Butane-1,4-diammonium bis(perchlorate) Charmaine Arderne* and Gert J. Kruger Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, Johannesburg, 2006, South Africa Correspondence e-mail: carderne@uj.ac.za. Refinement R[F 2 > 2(F 2)] = 0.056 wR(F 2) = 0.155 S = 1.17 793 reflections. 46 parameters H-atom parameters constrained ˚ 3 max = 0.47 e A ˚ 3 min = 0.44 e A. Table 1. Received 29 March 2011; accepted 31 March 2011. ˚ ,  ). Hydrogen-bond geometry (A. ˚; Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.005 A R factor = 0.056; wR factor = 0.155; data-to-parameter ratio = 17.2.. The butane-1,4-diammonium cation of the title compound, C4H14N22+2ClO4, 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 interactions to the perchlorate anion. Complex hydrogenbonded ring and chain motifs are also evident, in particular a 50-membered ring with graph-set notation R10 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).. D—H  A. D—H. H  A. D  A. D—H  A. N1—H1N  O1i N1—H1N  O1ii N1—H2N  O1 N1—H2N  O3. 0.89 0.89 0.89 0.89. 2.35 2.35 2.68 2.21. 3.035 (3) 3.035 (3) 3.435 (4) 3.0308 (14). 134 134 143 153. Symmetry codes: (i) x; y; z þ 1; (ii) x; y; z þ 1.. 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: XSEED (Barbour, 2001) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).. The authors acknowledge the National Research Foundation Thuthuka programme (GUN 66314) and the University of Johannesburg for funding and facilities for this study. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5503).. References. Experimental Crystal data C4H14N22+2ClO4 Mr = 289.07 Monoclinic, C2=m ˚ a = 19.4755 (10) A ˚ b = 5.6210 (3) A ˚ c = 5.3470 (2) A  = 97.222 (3). o1060. Arderne and Kruger. ˚3 V = 580.70 (5) A Z=2 Mo K radiation  = 0.59 mm1 T = 296 K 0.50  0.34  0.16 mm. Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. Blerk, C. van & Kruger, G. J. (2007). Acta Cryst. E63, o342–o344. Bruker (2008). AXScale, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Gabro, M., Lalancette, R. A. & Bernal, I. (2009). Acta Cryst. E65, o1352. Lemmerer, A. & Billing, D. G. (2006). Acta Cryst. E62, o1954–o1956. Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.. doi:10.1107/S1600536811012025. Acta Cryst. (2011). E67, o1060.

(2) supporting information. supporting information Acta Cryst. (2011). E67, o1060. [doi:10.1107/S1600536811012025]. Butane-1,4-diammonium bis(perchlorate) Charmaine Arderne and Gert J. Kruger S1. Comment The crystal structure of the title compound (I) adds to our current ongoing studies of long-chained diammonium mineral acid salts. Colourless rectangular crystals of butane-1,4-diammonium diperchlorate were synthesized and formed part of our structural chemistry study of the inorganic mineral acid salts of butane-1,4-diamine. The butane-1,4-diammonium cation lies over an inversion centre and a twofold rotation axis. It also straddles a crystallographic mirror plane. The asymmetric unit contains one-half of a perchlorate anion and one-half of the butane-1,4-diammonium cation. The hydrocarbon chain is also fully extended and is of necessity completely planar as it lies in the crystallographic mirror plane. The molecular structure of (I) is shown in Figure 1. Figure 2 illustrates the packing arrangement of the title compound (I). Single stacked layers of cations pack together with perchlorate anions inserted between the cation chains in line with the ammonium groups showing a distinct inorganic - organic layering effect that is a common feature of these long-chained diammonium salts. An extensive threedimensional hydrogen-bonding network is formed. A close-up view of the hydrogen bonding interactions can be viewed in Figure 3 where very clear evidence of bifurcated interactions can be seen on each hydrogen atom of both ammonium groups. The hydrogen bond distances and angles for (I) can be found in Table 2. Since the hydrogen bonding network is extremely intricate and complex, we focus on one particularly interesting hydrogen-bonding ring motif in the structure. Figure 4 shows a view of five diammonium cations and five perchlorate anions (viewed down the a axis) that are hydrogen bonded together to form a large, level 2, 50-membered ring motif with graph set notation R1010(50). Numerous other ring and chain motifs were identified with Mercury (Macrae et al.), but since the one in Figure 4 is the highest level motif obtainable in the structure, the other motifs of lower level are not depicted here. S2. Experimental The title compound was prepared by adding butane-1,4-diamine (0.50 g, 5.67 mmol) to 30% perchloric acid (HClO4, 2 ml, 9.138 mmol, Merck) in a sample vial. The mixture was then refluxed at 363 K for 2 h. The solution was cooled at 2 K h-1 to room temperature. Colourless crystals of butane-1,4-diammonium diperchlorate were collected and a suitable single-crystal was selected for the X-ray diffraction study. S3. Refinement Hydrogen atoms could be identified from the difference Fourier map but once these atoms were refined, their distances from the parent atoms were found to be significantly shorter than the ideal distances for C—H and N—H respectively. The H-atoms were therefore geometrically positioned and refined in the riding-model approximation, with C—H = 0.97 Å, N—H = 0.89 Å, and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(N). The highest peak in the final difference map is 0.69Å from O2. Acta Cryst. (2011). E67, o1060. sup-1.

(3) supporting information and the deepest hole is 0.69Å from Cl1.. Figure 1 Molecular structure of the title compound, with atomic numbering scheme and displacement ellipsoids drawn at the 50% probability level.. Figure 2 Packing arrangement of the title compound viewed down the b axis. Hydrogen bonds are indicated by red dashed lines.. Acta Cryst. (2011). E67, o1060. sup-2.

(4) supporting information. Figure 3 Close-up view of the title compound clearly showing the bifurcated hydrogen-bonding interactions. Hydrogen bonds are indicated by red dashed lines.. Acta Cryst. (2011). E67, o1060. sup-3.

(5) supporting information. Figure 4 Close up view of the title compound viewed down the a axis showing the 50-membered level 2 ring motif. Butane-1,4-diammonium bis(perchlorate) Crystal data C4H14N22+·2ClO4− Mr = 289.07 Monoclinic, C2/m Hall symbol: -C 2y 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. Acta Cryst. (2011). E67, o1060. F(000) = 300 Dx = 1.653 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1622 reflections θ = 3.8–28.2° µ = 0.59 mm−1 T = 296 K Block, colourless 0.50 × 0.34 × 0.16 mm. sup-4.

(6) supporting information Data collection Bruker APEXII CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans Absorption correction: multi-scan (AX-Scale; Bruker, 2008) Tmin = 0.757, Tmax = 0.912. 3067 measured reflections 793 independent reflections 694 reflections with I > 2s(I) Rint = 0.028 θmax = 28.3°, θmin = 3.8° h = −23→25 k = −7→7 l = −6→7. Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.056 wR(F2) = 0.155 S = 1.17 793 reflections 46 parameters 0 restraints Primary atom site location: structure-invariant direct methods. Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0955P)2 + 0.3477P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001 Δρmax = 0.47 e Å−3 Δρmin = −0.44 e Å−3. Special details 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 (Å2). C1 H1 C2 H2 Cl1 N1 H1N H2N O1 O2 O3. x. y. z. Uiso*/Ueq. 0.57860 (17) 0.5661 0.53822 (16) 0.5508 0.65841 (4) 0.65459 (14) 0.6762 0.6666 0.69616 (13) 0.59205 (16) 0.65031 (17). 0.0000 0.1394 0.0000 −0.1394 0.5000 0.0000 0.0000 0.1293 0.2898 (5) 0.5000 0.5000. 0.7538 (6) 0.8450 0.4976 (6) 0.4065 0.27016 (13) 0.7476 (5) 0.9045 0.6673 0.2214 (5) 0.1238 (6) 0.5341 (5). 0.0466 (8) 0.056* 0.0467 (8) 0.056* 0.0403 (3) 0.0450 (7) 0.068* 0.068* 0.0755 (7) 0.0698 (9) 0.0633 (8). Atomic displacement parameters (Å2). C1. U11. U22. U33. U12. U13. U23. 0.0461 (18). 0.061 (2). 0.0321 (15). 0.000. 0.0021 (12). 0.000. Acta Cryst. (2011). E67, o1060. sup-5.

(7) supporting information C2 Cl1 N1 O1 O2 O3. 0.0403 (18) 0.0480 (5) 0.0425 (15) 0.0818 (14) 0.0619 (18) 0.095 (2). 0.068 (2) 0.0380 (5) 0.0501 (17) 0.0697 (16) 0.069 (2) 0.0596 (17). 0.0315 (15) 0.0344 (5) 0.0398 (14) 0.0730 (14) 0.071 (2) 0.0377 (14). 0.000 0.000 0.000 0.0253 (12) 0.000 0.000. 0.0028 (12) 0.0031 (3) −0.0049 (11) 0.0014 (11) −0.0187 (14) 0.0171 (13). 0.000 0.000 0.000 −0.0236 (11) 0.000 0.000. Geometric parameters (Å, º) C1—N1 C1—C2 C1—H1 C2—C2i C2—H2 Cl1—O2. 1.484 (4) 1.492 (4) 0.9700 1.492 (6) 0.9700 1.424 (3). Cl1—O1 Cl1—O1ii Cl1—O3 N1—H1N N1—H2N. 1.433 (2) 1.433 (2) 1.440 (3) 0.8900 0.8900. N1—C1—C2 N1—C1—H1 C2—C1—H1 H1—C1—H1iii C1—C2—C2i C1—C2—H2 C2i—C2—H2 H2—C2—H2iii O2—Cl1—O1. 113.0 (3) 109.0 109.0 107.8 113.3 (3) 108.9 108.9 107.7 110.54 (12). O2—Cl1—O1ii O1—Cl1—O1ii O2—Cl1—O3 O1—Cl1—O3 O1ii—Cl1—O3 C1—N1—H1N C1—N1—H2N H1N—N1—H2N. 110.54 (12) 111.1 (2) 109.6 (2) 107.48 (13) 107.48 (13) 109.5 109.5 109.5. N1—C1—C2—C2i. 180.0. Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1, z; (iii) x, −y, z.. Hydrogen-bond geometry (Å, º) D—H···A iv. N1—H1N···O1 N1—H1N···O1v N1—H2N···O1 N1—H2N···O3. D—H. H···A. D···A. D—H···A. 0.89 0.89 0.89 0.89. 2.35 2.35 2.68 2.21. 3.035 (3) 3.035 (3) 3.435 (4) 3.0308 (14). 134 134 143 153. Symmetry codes: (iv) x, y, z+1; (v) x, −y, z+1.. Acta Cryst. (2011). E67, o1060. sup-6.

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