organic compounds
Hexane-1,6-diammonium hexafluorosilicate
aDépartement de Physique-Chimie, Laboratoire de Chimie, Centre Régional des Métiers de l'Education et de la Formation, Souissi Rabat, Morocco, bEquipe de Physico-Chimie des Matériaux Inorganiques, Université Ibn Tofail, Faculté des Sciences, BP 133, 14000 Kénitra, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: a_ouasri@yahoo.fr
The 6H18N22+·SiF62−, consists of one anion and one cation together with half of each of two cations and two anions located on inversion centres. The SiF62− octahedral anions are arranged to form sheets parallel to (011), which are linked into a three-dimensional network by the organic cations through N—H⋯F hydrogen bonds.
of the title organic–inorganic molecular salt, CCCDC reference: 977855
Related literature
For background to potential physical properties of alkyldiammonium halogenometallate salts, see: Ouasri et al. (2003); Elyoubi et al. (2004). For the structures of related compounds, see: Jeghnou et al. (2005); Ouasri et al. (2012, 2013a,b); Rhandour et al. (2011); Elaoud et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 977855
https://doi.org/10.1107/S1600536813034144/rz5101sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813034144/rz5101Isup2.hkl
Single crystals of the title compound were obtained by slow evaporation at room temperature of an aqueous solution containing stoichiometric amounts of 1,6-hexanediamine NH2(CH2)6NH2 and hexafluorosilicic acid H2SiF6.
H atoms were located in a difference Fourier map and treated as riding, with C—H = 0.97 Å, N—H = 0.89 Å, and with Uiso(H) = 1.2 Ueq (C, N). Four outlier (0 1 0, 0 0 1, 0 1 1, 1 -1 1) were omitted in the last
cycles.The title compound belongs to the alkyldiammonium halogenometallate salts family of general formula (NH3(CH2)nNH3)MX6 where M is Sn, Si, Te and X is Cl, Br, I and F. These compounds have recently attracted the interest of many investigators due to their potential physical properties (Ouasri et al., 2003; Elyoubi et al., 2004). X-ray, thermal and vibrational studies of phase transitions have been performed for others compounds which belong to the alkyldiammonium halogenobismuthate salts family such as the pentachlorobismuthate derivative (NH3(CH2)nNH3)BiCl5 (Jeghnou et al., 2005; Ouasri et al., 2012; Rhandour et al., 2011; Ouasri et al., 2013a; Ouasri et al., 2013b). It was found that hexahalogenometallates (NH3(CH2)nNH3)MX6 (where M: Sn, Te; X: Cl, Br, I) have been more studied and evoked that their hexafluorosilicate homologous, whose (NH3(CH2)6NH3)SiF6 (Elaoud et al., 1995) is the only compound known to date. The aim of the present paper was to study the structure of the recently synthesized hexyldiammonium hexafluorosilicate (NH3(CH2)6NH3)SiF6 crystals by X-ray diffraction at room temperature.
The structure of the title compound is built up from inorganic anions linked to organic cations through hydrogen bonds as shown in Fig. 1. In this structure, all atoms are in general positions, except two silicon atoms [Si2 (0, 1/2, 1/2); Si3 (0, 0, 0)] located at inversion centres of the P1 Moreover, the contains one organic cation and two halves of cations located about an inversion centre. Each silicon atom is surrounded by six fluorine anions in a slightly distorted SiF62- octahedral geometry. The SiF62- octahedra form two-dimensional layers parallel to the (0 1 1) plane. The hexanediammonium cations fill the space between the inorganic sheets, forming a three-dimensional network by N–H···F hydrogen bonds (Fig. 2; Table 1).
For background to potential physical properties of alkyldiammonium halogenometallate salts, see: Ouasri et al. (2003); Elyoubi et al. (2004). For the structures of related compounds, see: Jeghnou et al. (2005); Ouasri et al. (2012, 2013a,b); Rhandour et al. (2011); Elaoud et al. (1995).
Data collection: APEX2 (Bruker, 2009); cell
SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles. Symmetry codes: (i) -x, 1.-y, -z; (ii) -x, 2.-y, -z; (iii) -x, 1.-y, 1.-z; (iv) -x, 2.-y, 1.-z. | |
Fig. 2. Packing diagram of the title compound, showing inorganic layers linked through N–H···F hydrogen bonds (dashed lines). |
C6H18N22+·SiF62− | Z = 4 |
Mr = 260.31 | F(000) = 544 |
Triclinic, P1 | Dx = 1.480 Mg m−3 |
a = 5.8965 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.6946 (5) Å | Cell parameters from 4760 reflections |
c = 14.4945 (5) Å | θ = 2.0–26.4° |
α = 91.379 (2)° | µ = 0.25 mm−1 |
β = 92.797 (2)° | T = 296 K |
γ = 90.906 (2)° | Block, colourless |
V = 1168.53 (7) Å3 | 0.37 × 0.33 × 0.28 mm |
Bruker X8 APEX diffractometer | 4760 independent reflections |
Radiation source: fine-focus sealed tube | 3618 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 26.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −7→7 |
Tmin = 0.686, Tmax = 0.747 | k = −17→17 |
29127 measured reflections | l = −18→18 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0734P)2 + 1.0436P] where P = (Fo2 + 2Fc2)/3 |
4760 reflections | (Δ/σ)max < 0.001 |
274 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C6H18N22+·SiF62− | γ = 90.906 (2)° |
Mr = 260.31 | V = 1168.53 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 5.8965 (2) Å | Mo Kα radiation |
b = 13.6946 (5) Å | µ = 0.25 mm−1 |
c = 14.4945 (5) Å | T = 296 K |
α = 91.379 (2)° | 0.37 × 0.33 × 0.28 mm |
β = 92.797 (2)° |
Bruker X8 APEX diffractometer | 4760 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3618 reflections with I > 2σ(I) |
Tmin = 0.686, Tmax = 0.747 | Rint = 0.023 |
29127 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.46 e Å−3 |
4760 reflections | Δρmin = −0.26 e Å−3 |
274 parameters |
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 | 0.4600 (7) | 0.7541 (2) | 0.9702 (2) | 0.0601 (9) | |
H1A | 0.2997 | 0.7367 | 0.9682 | 0.072* | |
H1B | 0.5425 | 0.7018 | 1.0000 | 0.072* | |
C2 | 0.5353 (7) | 0.7632 (3) | 0.8734 (2) | 0.0632 (9) | |
H2A | 0.4561 | 0.8168 | 0.8443 | 0.076* | |
H2B | 0.6965 | 0.7788 | 0.8755 | 0.076* | |
C3 | 0.4917 (8) | 0.6720 (3) | 0.8158 (2) | 0.0773 (12) | |
H3A | 0.3295 | 0.6585 | 0.8117 | 0.093* | |
H3B | 0.5638 | 0.6180 | 0.8471 | 0.093* | |
C4 | 0.5760 (8) | 0.6754 (3) | 0.7179 (2) | 0.0828 (12) | |
H4A | 0.7366 | 0.6925 | 0.7221 | 0.099* | |
H4B | 0.5608 | 0.6103 | 0.6902 | 0.099* | |
C5 | 0.4604 (8) | 0.7437 (3) | 0.6558 (2) | 0.0739 (11) | |
H5A | 0.4718 | 0.8083 | 0.6848 | 0.089* | |
H5B | 0.3006 | 0.7254 | 0.6507 | 0.089* | |
C6 | 0.5433 (7) | 0.7508 (2) | 0.5600 (2) | 0.0624 (9) | |
H6A | 0.4661 | 0.8039 | 0.5292 | 0.075* | |
H6B | 0.7043 | 0.7669 | 0.5642 | 0.075* | |
C7 | 0.0516 (6) | 1.0370 (2) | 0.2857 (2) | 0.0523 (7) | |
H7A | −0.0151 | 1.0834 | 0.2432 | 0.063* | |
H7B | 0.2133 | 1.0513 | 0.2925 | 0.063* | |
C8 | −0.0506 (6) | 1.0498 (2) | 0.3775 (2) | 0.0552 (8) | |
H8A | −0.2110 | 1.0330 | 0.3703 | 0.066* | |
H8B | −0.0383 | 1.1184 | 0.3959 | 0.066* | |
C9 | 0.0530 (6) | 0.9906 (2) | 0.45450 (19) | 0.0552 (8) | |
H9A | 0.0358 | 0.9217 | 0.4379 | 0.066* | |
H9B | 0.2143 | 1.0058 | 0.4614 | 0.066* | |
C10 | −0.0545 (6) | 0.5465 (2) | 0.21254 (19) | 0.0497 (7) | |
H10A | −0.2183 | 0.5377 | 0.2075 | 0.060* | |
H10B | 0.0104 | 0.4860 | 0.2339 | 0.060* | |
C11 | 0.0292 (6) | 0.5675 (2) | 0.11971 (19) | 0.0524 (7) | |
H11A | 0.1936 | 0.5724 | 0.1243 | 0.063* | |
H11B | −0.0279 | 0.6302 | 0.1003 | 0.063* | |
C12 | −0.0417 (7) | 0.4908 (3) | 0.0471 (2) | 0.0617 (9) | |
H12A | 0.0139 | 0.4281 | 0.0672 | 0.074* | |
H12B | −0.2062 | 0.4864 | 0.0426 | 0.074* | |
N1 | 0.4970 (3) | 0.84453 (16) | 1.02554 (13) | 0.0367 (5) | |
H1NB | 0.4442 | 0.8948 | 0.9937 | 0.044* | |
H1NA | 0.6449 | 0.8535 | 1.0388 | 0.044* | |
H1NC | 0.4243 | 0.8402 | 1.0777 | 0.044* | |
N2 | 0.5073 (3) | 0.66128 (16) | 0.50333 (14) | 0.0357 (5) | |
H2NA | 0.5824 | 0.6126 | 0.5298 | 0.043* | |
H2NC | 0.5580 | 0.6706 | 0.4473 | 0.043* | |
H2NB | 0.3597 | 0.6463 | 0.4985 | 0.043* | |
N3 | 0.0159 (3) | 0.93712 (15) | 0.24637 (13) | 0.0341 (5) | |
H3NA | 0.0877 | 0.8948 | 0.2826 | 0.041* | |
H3NB | 0.0703 | 0.9338 | 0.1902 | 0.041* | |
H3NC | −0.1320 | 0.9226 | 0.2426 | 0.041* | |
N4 | 0.0039 (3) | 0.62479 (15) | 0.28063 (13) | 0.0326 (4) | |
H4NA | −0.0539 | 0.6104 | 0.3343 | 0.039* | |
H4NB | −0.0532 | 0.6808 | 0.2609 | 0.039* | |
H4NC | 0.1542 | 0.6308 | 0.2880 | 0.039* | |
F1 | 0.3057 (2) | 0.80063 (13) | 0.34886 (10) | 0.0471 (4) | |
F2 | 0.3060 (2) | 0.77137 (12) | 0.18810 (10) | 0.0437 (4) | |
F3 | 0.5306 (3) | 0.90186 (12) | 0.25488 (13) | 0.0553 (5) | |
F4 | 0.7096 (2) | 0.76175 (13) | 0.19650 (11) | 0.0476 (4) | |
F5 | 0.7122 (3) | 0.79006 (15) | 0.35786 (11) | 0.0560 (5) | |
F6 | 0.4882 (3) | 0.66026 (12) | 0.29172 (12) | 0.0496 (4) | |
F7 | 0.2030 (2) | 0.49066 (13) | 0.42253 (11) | 0.0483 (4) | |
F8 | 0.0188 (3) | 0.62264 (11) | 0.49428 (12) | 0.0516 (4) | |
F9 | −0.2025 (3) | 0.49935 (13) | 0.41489 (11) | 0.0514 (4) | |
F10 | 0.0226 (3) | 1.11843 (13) | −0.02764 (13) | 0.0575 (5) | |
F11 | −0.1963 (2) | 1.02734 (14) | 0.07661 (10) | 0.0519 (5) | |
F12 | 0.2087 (2) | 1.01509 (14) | 0.08206 (10) | 0.0505 (4) | |
Si1 | 0.50922 (10) | 0.78157 (5) | 0.27367 (5) | 0.0328 (2) | |
Si2 | 0.0000 | 0.5000 | 0.5000 | 0.0339 (2) | |
Si3 | 0.0000 | 1.0000 | 0.0000 | 0.0370 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.084 (2) | 0.0542 (19) | 0.0415 (16) | −0.0097 (17) | 0.0083 (15) | −0.0045 (14) |
C2 | 0.081 (2) | 0.064 (2) | 0.0448 (17) | −0.0093 (18) | 0.0126 (16) | −0.0058 (15) |
C3 | 0.128 (4) | 0.057 (2) | 0.0463 (19) | −0.002 (2) | 0.007 (2) | −0.0031 (16) |
C4 | 0.118 (3) | 0.081 (3) | 0.050 (2) | 0.025 (2) | 0.005 (2) | −0.0012 (19) |
C5 | 0.105 (3) | 0.067 (2) | 0.0488 (19) | 0.016 (2) | −0.0007 (19) | −0.0104 (17) |
C6 | 0.092 (3) | 0.0506 (19) | 0.0448 (17) | −0.0089 (17) | 0.0047 (16) | −0.0023 (14) |
C7 | 0.073 (2) | 0.0411 (16) | 0.0428 (16) | −0.0057 (14) | 0.0037 (14) | 0.0020 (12) |
C8 | 0.076 (2) | 0.0458 (17) | 0.0431 (16) | 0.0089 (15) | 0.0005 (14) | −0.0075 (13) |
C9 | 0.074 (2) | 0.0551 (19) | 0.0367 (15) | 0.0095 (16) | 0.0021 (14) | −0.0084 (13) |
C10 | 0.0667 (19) | 0.0424 (16) | 0.0400 (15) | −0.0072 (14) | 0.0086 (13) | −0.0043 (12) |
C11 | 0.068 (2) | 0.0513 (18) | 0.0378 (15) | −0.0085 (15) | 0.0098 (13) | −0.0074 (13) |
C12 | 0.085 (2) | 0.060 (2) | 0.0407 (17) | −0.0171 (18) | 0.0137 (16) | −0.0115 (14) |
N1 | 0.0343 (11) | 0.0477 (13) | 0.0284 (10) | −0.0005 (9) | 0.0031 (8) | 0.0055 (9) |
N2 | 0.0327 (11) | 0.0439 (12) | 0.0312 (10) | 0.0027 (9) | 0.0046 (8) | 0.0050 (9) |
N3 | 0.0349 (11) | 0.0409 (12) | 0.0267 (10) | 0.0020 (9) | 0.0030 (8) | 0.0023 (8) |
N4 | 0.0320 (10) | 0.0375 (11) | 0.0289 (10) | 0.0021 (8) | 0.0038 (8) | 0.0032 (8) |
F1 | 0.0376 (8) | 0.0681 (11) | 0.0373 (8) | 0.0117 (7) | 0.0124 (6) | 0.0080 (7) |
F2 | 0.0325 (8) | 0.0626 (10) | 0.0359 (8) | 0.0011 (7) | −0.0024 (6) | 0.0082 (7) |
F3 | 0.0435 (9) | 0.0435 (9) | 0.0799 (12) | 0.0011 (7) | 0.0045 (8) | 0.0161 (8) |
F4 | 0.0340 (8) | 0.0681 (11) | 0.0431 (9) | 0.0119 (7) | 0.0149 (6) | 0.0189 (8) |
F5 | 0.0363 (8) | 0.0857 (13) | 0.0454 (9) | 0.0008 (8) | −0.0084 (7) | 0.0099 (9) |
F6 | 0.0425 (9) | 0.0421 (9) | 0.0662 (11) | 0.0062 (7) | 0.0118 (7) | 0.0212 (8) |
F7 | 0.0371 (8) | 0.0635 (11) | 0.0468 (9) | 0.0107 (7) | 0.0178 (7) | 0.0171 (8) |
F8 | 0.0465 (9) | 0.0389 (9) | 0.0708 (11) | 0.0031 (7) | 0.0104 (8) | 0.0149 (8) |
F9 | 0.0358 (8) | 0.0743 (12) | 0.0443 (9) | −0.0001 (8) | −0.0040 (7) | 0.0178 (8) |
F10 | 0.0428 (9) | 0.0582 (11) | 0.0726 (12) | −0.0008 (8) | 0.0034 (8) | 0.0268 (9) |
F11 | 0.0351 (8) | 0.0858 (13) | 0.0366 (8) | 0.0119 (8) | 0.0090 (6) | 0.0158 (8) |
F12 | 0.0311 (8) | 0.0823 (13) | 0.0380 (8) | −0.0017 (8) | −0.0052 (6) | 0.0121 (8) |
Si1 | 0.0246 (3) | 0.0431 (4) | 0.0318 (4) | 0.0035 (3) | 0.0040 (3) | 0.0126 (3) |
Si2 | 0.0250 (5) | 0.0411 (6) | 0.0368 (5) | 0.0039 (4) | 0.0067 (4) | 0.0142 (4) |
Si3 | 0.0244 (5) | 0.0575 (7) | 0.0298 (5) | 0.0011 (4) | 0.0022 (4) | 0.0166 (4) |
C1—N1 | 1.466 (4) | C11—H11B | 0.9700 |
C1—C2 | 1.500 (4) | C12—C12ii | 1.499 (6) |
C1—H1A | 0.9700 | C12—H12A | 0.9700 |
C1—H1B | 0.9700 | C12—H12B | 0.9700 |
C2—C3 | 1.498 (5) | N1—H1NB | 0.8900 |
C2—H2A | 0.9700 | N1—H1NA | 0.8900 |
C2—H2B | 0.9700 | N1—H1NC | 0.8900 |
C3—C4 | 1.527 (5) | N2—H2NA | 0.8900 |
C3—H3A | 0.9700 | N2—H2NC | 0.8900 |
C3—H3B | 0.9700 | N2—H2NB | 0.8900 |
C4—C5 | 1.467 (5) | N3—H3NA | 0.8900 |
C4—H4A | 0.9700 | N3—H3NB | 0.8900 |
C4—H4B | 0.9700 | N3—H3NC | 0.8900 |
C5—C6 | 1.499 (5) | N4—H4NA | 0.8900 |
C5—H5A | 0.9700 | N4—H4NB | 0.8900 |
C5—H5B | 0.9700 | N4—H4NC | 0.8900 |
C6—N2 | 1.466 (4) | F1—Si1 | 1.6794 (15) |
C6—H6A | 0.9700 | F2—Si1 | 1.6837 (15) |
C6—H6B | 0.9700 | F3—Si1 | 1.6798 (17) |
C7—N3 | 1.478 (3) | F4—Si1 | 1.6868 (15) |
C7—C8 | 1.495 (4) | F5—Si1 | 1.6677 (16) |
C7—H7A | 0.9700 | F6—Si1 | 1.6915 (16) |
C7—H7B | 0.9700 | F7—Si2 | 1.6848 (14) |
C8—C9 | 1.507 (4) | F8—Si2 | 1.6858 (16) |
C8—H8A | 0.9700 | F9—Si2 | 1.6741 (15) |
C8—H8B | 0.9700 | F10—Si3 | 1.6848 (17) |
C9—C9i | 1.506 (5) | F11—Si3 | 1.6830 (14) |
C9—H9A | 0.9700 | F12—Si3 | 1.6759 (14) |
C9—H9B | 0.9700 | Si2—F9iii | 1.6741 (15) |
C10—N4 | 1.465 (3) | Si2—F7iii | 1.6849 (14) |
C10—C11 | 1.489 (4) | Si2—F8iii | 1.6858 (16) |
C10—H10A | 0.9700 | Si3—F12iv | 1.6760 (14) |
C10—H10B | 0.9700 | Si3—F11iv | 1.6830 (14) |
C11—C12 | 1.508 (4) | Si3—F10iv | 1.6848 (17) |
C11—H11A | 0.9700 | ||
N1—C1—C2 | 112.6 (3) | H12A—C12—H12B | 107.6 |
N1—C1—H1A | 109.1 | C1—N1—H1NB | 109.5 |
C2—C1—H1A | 109.1 | C1—N1—H1NA | 109.5 |
N1—C1—H1B | 109.1 | H1NB—N1—H1NA | 109.5 |
C2—C1—H1B | 109.1 | C1—N1—H1NC | 109.5 |
H1A—C1—H1B | 107.8 | H1NB—N1—H1NC | 109.5 |
C3—C2—C1 | 112.9 (3) | H1NA—N1—H1NC | 109.5 |
C3—C2—H2A | 109.0 | C6—N2—H2NA | 109.5 |
C1—C2—H2A | 109.0 | C6—N2—H2NC | 109.5 |
C3—C2—H2B | 109.0 | H2NA—N2—H2NC | 109.5 |
C1—C2—H2B | 109.0 | C6—N2—H2NB | 109.5 |
H2A—C2—H2B | 107.8 | H2NA—N2—H2NB | 109.5 |
C2—C3—C4 | 115.1 (3) | H2NC—N2—H2NB | 109.5 |
C2—C3—H3A | 108.5 | C7—N3—H3NA | 109.5 |
C4—C3—H3A | 108.5 | C7—N3—H3NB | 109.5 |
C2—C3—H3B | 108.5 | H3NA—N3—H3NB | 109.5 |
C4—C3—H3B | 108.5 | C7—N3—H3NC | 109.5 |
H3A—C3—H3B | 107.5 | H3NA—N3—H3NC | 109.5 |
C5—C4—C3 | 116.0 (3) | H3NB—N3—H3NC | 109.5 |
C5—C4—H4A | 108.3 | C10—N4—H4NA | 109.5 |
C3—C4—H4A | 108.3 | C10—N4—H4NB | 109.5 |
C5—C4—H4B | 108.3 | H4NA—N4—H4NB | 109.5 |
C3—C4—H4B | 108.3 | C10—N4—H4NC | 109.5 |
H4A—C4—H4B | 107.4 | H4NA—N4—H4NC | 109.5 |
C4—C5—C6 | 117.4 (3) | H4NB—N4—H4NC | 109.5 |
C4—C5—H5A | 108.0 | F5—Si1—F1 | 91.67 (8) |
C6—C5—H5A | 108.0 | F5—Si1—F3 | 91.24 (10) |
C4—C5—H5B | 108.0 | F1—Si1—F3 | 91.04 (9) |
C6—C5—H5B | 108.0 | F5—Si1—F2 | 179.11 (10) |
H5A—C5—H5B | 107.2 | F1—Si1—F2 | 88.89 (8) |
N2—C6—C5 | 114.0 (3) | F3—Si1—F2 | 89.43 (9) |
N2—C6—H6A | 108.8 | F5—Si1—F4 | 89.45 (8) |
C5—C6—H6A | 108.8 | F1—Si1—F4 | 178.85 (9) |
N2—C6—H6B | 108.8 | F3—Si1—F4 | 89.17 (9) |
C5—C6—H6B | 108.8 | F2—Si1—F4 | 89.98 (8) |
H6A—C6—H6B | 107.6 | F5—Si1—F6 | 88.99 (9) |
N3—C7—C8 | 112.4 (2) | F1—Si1—F6 | 89.33 (8) |
N3—C7—H7A | 109.1 | F3—Si1—F6 | 179.56 (10) |
C8—C7—H7A | 109.1 | F2—Si1—F6 | 90.33 (9) |
N3—C7—H7B | 109.1 | F4—Si1—F6 | 90.46 (8) |
C8—C7—H7B | 109.1 | F9iii—Si2—F9 | 180.0 |
H7A—C7—H7B | 107.9 | F9iii—Si2—F7 | 89.15 (8) |
C7—C8—C9 | 115.8 (3) | F9—Si2—F7 | 90.85 (8) |
C7—C8—H8A | 108.3 | F9iii—Si2—F7iii | 90.85 (8) |
C9—C8—H8A | 108.3 | F9—Si2—F7iii | 89.15 (8) |
C7—C8—H8B | 108.3 | F7—Si2—F7iii | 180.0 |
C9—C8—H8B | 108.3 | F9iii—Si2—F8 | 90.78 (9) |
H8A—C8—H8B | 107.4 | F9—Si2—F8 | 89.22 (9) |
C9i—C9—C8 | 112.9 (3) | F7—Si2—F8 | 89.29 (8) |
C9i—C9—H9A | 109.0 | F7iii—Si2—F8 | 90.71 (8) |
C8—C9—H9A | 109.0 | F9iii—Si2—F8iii | 89.22 (9) |
C9i—C9—H9B | 109.0 | F9—Si2—F8iii | 90.78 (9) |
C8—C9—H9B | 109.0 | F7—Si2—F8iii | 90.71 (8) |
H9A—C9—H9B | 107.8 | F7iii—Si2—F8iii | 89.29 (8) |
N4—C10—C11 | 112.4 (2) | F8—Si2—F8iii | 180.0 |
N4—C10—H10A | 109.1 | F12—Si3—F12iv | 180.0 |
C11—C10—H10A | 109.1 | F12—Si3—F11iv | 89.08 (8) |
N4—C10—H10B | 109.1 | F12iv—Si3—F11iv | 90.92 (8) |
C11—C10—H10B | 109.1 | F12—Si3—F11 | 90.92 (8) |
H10A—C10—H10B | 107.8 | F12iv—Si3—F11 | 89.08 (8) |
C10—C11—C12 | 113.3 (3) | F11iv—Si3—F11 | 180.000 (1) |
C10—C11—H11A | 108.9 | F12—Si3—F10iv | 89.24 (9) |
C12—C11—H11A | 108.9 | F12iv—Si3—F10iv | 90.76 (9) |
C10—C11—H11B | 108.9 | F11iv—Si3—F10iv | 90.66 (9) |
C12—C11—H11B | 108.9 | F11—Si3—F10iv | 89.34 (9) |
H11A—C11—H11B | 107.7 | F12—Si3—F10 | 90.76 (9) |
C12ii—C12—C11 | 114.8 (3) | F12iv—Si3—F10 | 89.24 (9) |
C12ii—C12—H12A | 108.6 | F11iv—Si3—F10 | 89.34 (9) |
C11—C12—H12A | 108.6 | F11—Si3—F10 | 90.66 (9) |
C12ii—C12—H12B | 108.6 | F10iv—Si3—F10 | 180.00 (12) |
C11—C12—H12B | 108.6 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z; (iii) −x, −y+1, −z+1; (iv) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2NC···F5 | 0.89 | 2.31 | 3.062 (3) | 142 |
N2—H2NC···F6 | 0.89 | 2.27 | 3.063 (3) | 148 |
N2—H2NB···F7 | 0.89 | 2.52 | 3.095 (3) | 123 |
N2—H2NB···F8 | 0.89 | 2.03 | 2.917 (3) | 175 |
N3—H3NA···F1 | 0.89 | 2.06 | 2.934 (3) | 169 |
N4—H4NA···F8 | 0.89 | 2.34 | 3.095 (3) | 143 |
N4—H4NA···F9 | 0.89 | 2.14 | 2.923 (3) | 146 |
N4—H4NC···F6 | 0.89 | 2.00 | 2.885 (3) | 172 |
N1—H1NB···F11i | 0.89 | 2.07 | 2.895 (3) | 155 |
N1—H1NA···F10v | 0.89 | 2.01 | 2.869 (3) | 163 |
N1—H1NC···F2vi | 0.89 | 2.02 | 2.857 (2) | 155 |
N2—H2NA···F7vii | 0.89 | 2.02 | 2.906 (3) | 170 |
N3—H3NB···F10iv | 0.89 | 2.48 | 3.239 (3) | 144 |
N3—H3NB···F12 | 0.89 | 2.13 | 2.907 (2) | 145 |
N3—H3NC···F3viii | 0.89 | 2.02 | 2.904 (3) | 170 |
N3—H3NC···F4viii | 0.89 | 2.44 | 3.034 (3) | 124 |
N4—H4NB···F4viii | 0.89 | 2.01 | 2.832 (3) | 154 |
N4—H4NB···F5viii | 0.89 | 2.51 | 3.086 (3) | 123 |
Symmetry codes: (i) −x, −y+2, −z+1; (iv) −x, −y+2, −z; (v) −x+1, −y+2, −z+1; (vi) x, y, z+1; (vii) −x+1, −y+1, −z+1; (viii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2NC···F5 | 0.89 | 2.31 | 3.062 (3) | 141.6 |
N2—H2NC···F6 | 0.89 | 2.27 | 3.063 (3) | 147.8 |
N2—H2NB···F7 | 0.89 | 2.52 | 3.095 (3) | 123.3 |
N2—H2NB···F8 | 0.89 | 2.03 | 2.917 (3) | 175.0 |
N3—H3NA···F1 | 0.89 | 2.06 | 2.934 (3) | 168.6 |
N4—H4NA···F8 | 0.89 | 2.34 | 3.095 (3) | 142.8 |
N4—H4NA···F9 | 0.89 | 2.14 | 2.923 (3) | 146.1 |
N4—H4NC···F6 | 0.89 | 2.00 | 2.885 (3) | 171.6 |
N1—H1NB···F11i | 0.89 | 2.07 | 2.895 (3) | 154.6 |
N1—H1NA···F10ii | 0.89 | 2.01 | 2.869 (3) | 162.6 |
N1—H1NC···F2iii | 0.89 | 2.02 | 2.857 (2) | 155.3 |
N2—H2NA···F7iv | 0.89 | 2.02 | 2.906 (3) | 170.4 |
N3—H3NB···F10v | 0.89 | 2.48 | 3.239 (3) | 143.6 |
N3—H3NB···F12 | 0.89 | 2.13 | 2.907 (2) | 145.3 |
N3—H3NC···F3vi | 0.89 | 2.02 | 2.904 (3) | 170.3 |
N3—H3NC···F4vi | 0.89 | 2.44 | 3.034 (3) | 124.1 |
N4—H4NB···F4vi | 0.89 | 2.01 | 2.832 (3) | 153.7 |
N4—H4NB···F5vi | 0.89 | 2.51 | 3.086 (3) | 123.2 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1; (v) −x, −y+2, −z; (vi) x−1, y, z. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound belongs to the alkyldiammonium halogenometallate salts family of general formula (NH3(CH2)nNH3)MX6 where M is Sn, Si, Te and X is Cl, Br, I and F. These compounds have recently attracted the interest of many investigators due to their potential physical properties (Ouasri et al., 2003; Elyoubi et al., 2004). X-ray, thermal and vibrational studies of phase transitions have been performed for others compounds which belong to the alkyldiammonium halogenobismuthate salts family such as the pentachlorobismuthate derivative (NH3(CH2)nNH3)BiCl5 (Jeghnou et al., 2005; Ouasri et al., 2012; Rhandour et al., 2011; Ouasri et al., 2013a; Ouasri et al., 2013b). It was found that hexahalogenometallates (NH3(CH2)nNH3)MX6 (where M: Sn, Te; X: Cl, Br, I) have been more studied and evoked that their hexafluorosilicate homologous, whose (NH3(CH2)6NH3)SiF6 (Elaoud et al., 1995) is the only compound known to date. The aim of the present paper was to study the structure of the recently synthesized hexyldiammonium hexafluorosilicate (NH3(CH2)6NH3)SiF6 crystals by X-ray diffraction at room temperature.
The structure of the title compound is built up from inorganic anions linked to organic cations through hydrogen bonds as shown in Fig. 1. In this structure, all atoms are in general positions, except two silicon atoms [Si2 (0, 1/2, 1/2); Si3 (0, 0, 0)] located at inversion centres of the P1 space group. Moreover, the unit cell contains one organic cation and two halves of cations located about an inversion centre. Each silicon atom is surrounded by six fluorine anions in a slightly distorted SiF62- octahedral geometry. The SiF62- octahedra form two-dimensional layers parallel to the (0 1 1) plane. The hexanediammonium cations fill the space between the inorganic sheets, forming a three-dimensional network by N–H···F hydrogen bonds (Fig. 2; Table 1).