Literature DB >> 24527021

Hexane-1,6-di-ammonium hexa-fluoro-silicate.

Ali Ouasri1, Ali Rhandour2, Mohamed Saadi3, Lahcen El Ammari3.   

Abstract

The asymmetric unit of the title organic-inorganic molecular salt, C6H18N2 (2+)·SiF6 (2-), consists of one anion and one cation together with half of each of two cations and two anions located on inversion centres. The SiF6 (2-) octa-hedral 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.

Entities:  

Year:  2013        PMID: 24527021      PMCID: PMC3914114          DOI: 10.1107/S1600536813034144

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


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

C6H18N2 2+·SiF6 2− M = 260.31 Triclinic, a = 5.8965 (2) Å b = 13.6946 (5) Å c = 14.4945 (5) Å α = 91.379 (2)° β = 92.797 (2)° γ = 90.906 (2)° V = 1168.53 (7) Å3 Z = 4 Mo Kα radiation μ = 0.25 mm−1 T = 296 K 0.37 × 0.33 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.686, T max = 0.747 29127 measured reflections 4760 independent reflections 3618 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.159 S = 1.06 4760 reflections 274 parameters H-atom parameters constrained Δρmax = 0.46 e Å−3 Δρmin = −0.26 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: 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 ▶). Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813034144/rz5101sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034144/rz5101Isup2.hkl Additional supporting information: crystallographic information; 3D view; checkCIF report
C6H18N22+·SiF62Z = 4
Mr = 260.31F(000) = 544
Triclinic, P1Dx = 1.480 Mg m3
a = 5.8965 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.6946 (5) ÅCell parameters from 4760 reflections
c = 14.4945 (5) Åθ = 2.0–26.4°
α = 91.379 (2)°µ = 0.25 mm1
β = 92.797 (2)°T = 296 K
γ = 90.906 (2)°Block, colourless
V = 1168.53 (7) Å30.37 × 0.33 × 0.28 mm
Bruker X8 APEX diffractometer4760 independent reflections
Radiation source: fine-focus sealed tube3618 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −7→7
Tmin = 0.686, Tmax = 0.747k = −17→17
29127 measured reflectionsl = −18→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0734P)2 + 1.0436P] where P = (Fo2 + 2Fc2)/3
4760 reflections(Δ/σ)max < 0.001
274 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = −0.26 e Å3
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.
xyzUiso*/Ueq
C10.4600 (7)0.7541 (2)0.9702 (2)0.0601 (9)
H1A0.29970.73670.96820.072*
H1B0.54250.70181.00000.072*
C20.5353 (7)0.7632 (3)0.8734 (2)0.0632 (9)
H2A0.45610.81680.84430.076*
H2B0.69650.77880.87550.076*
C30.4917 (8)0.6720 (3)0.8158 (2)0.0773 (12)
H3A0.32950.65850.81170.093*
H3B0.56380.61800.84710.093*
C40.5760 (8)0.6754 (3)0.7179 (2)0.0828 (12)
H4A0.73660.69250.72210.099*
H4B0.56080.61030.69020.099*
C50.4604 (8)0.7437 (3)0.6558 (2)0.0739 (11)
H5A0.47180.80830.68480.089*
H5B0.30060.72540.65070.089*
C60.5433 (7)0.7508 (2)0.5600 (2)0.0624 (9)
H6A0.46610.80390.52920.075*
H6B0.70430.76690.56420.075*
C70.0516 (6)1.0370 (2)0.2857 (2)0.0523 (7)
H7A−0.01511.08340.24320.063*
H7B0.21331.05130.29250.063*
C8−0.0506 (6)1.0498 (2)0.3775 (2)0.0552 (8)
H8A−0.21101.03300.37030.066*
H8B−0.03831.11840.39590.066*
C90.0530 (6)0.9906 (2)0.45450 (19)0.0552 (8)
H9A0.03580.92170.43790.066*
H9B0.21431.00580.46140.066*
C10−0.0545 (6)0.5465 (2)0.21254 (19)0.0497 (7)
H10A−0.21830.53770.20750.060*
H10B0.01040.48600.23390.060*
C110.0292 (6)0.5675 (2)0.11971 (19)0.0524 (7)
H11A0.19360.57240.12430.063*
H11B−0.02790.63020.10030.063*
C12−0.0417 (7)0.4908 (3)0.0471 (2)0.0617 (9)
H12A0.01390.42810.06720.074*
H12B−0.20620.48640.04260.074*
N10.4970 (3)0.84453 (16)1.02554 (13)0.0367 (5)
H1NB0.44420.89480.99370.044*
H1NA0.64490.85351.03880.044*
H1NC0.42430.84021.07770.044*
N20.5073 (3)0.66128 (16)0.50333 (14)0.0357 (5)
H2NA0.58240.61260.52980.043*
H2NC0.55800.67060.44730.043*
H2NB0.35970.64630.49850.043*
N30.0159 (3)0.93712 (15)0.24637 (13)0.0341 (5)
H3NA0.08770.89480.28260.041*
H3NB0.07030.93380.19020.041*
H3NC−0.13200.92260.24260.041*
N40.0039 (3)0.62479 (15)0.28063 (13)0.0326 (4)
H4NA−0.05390.61040.33430.039*
H4NB−0.05320.68080.26090.039*
H4NC0.15420.63080.28800.039*
F10.3057 (2)0.80063 (13)0.34886 (10)0.0471 (4)
F20.3060 (2)0.77137 (12)0.18810 (10)0.0437 (4)
F30.5306 (3)0.90186 (12)0.25488 (13)0.0553 (5)
F40.7096 (2)0.76175 (13)0.19650 (11)0.0476 (4)
F50.7122 (3)0.79006 (15)0.35786 (11)0.0560 (5)
F60.4882 (3)0.66026 (12)0.29172 (12)0.0496 (4)
F70.2030 (2)0.49066 (13)0.42253 (11)0.0483 (4)
F80.0188 (3)0.62264 (11)0.49428 (12)0.0516 (4)
F9−0.2025 (3)0.49935 (13)0.41489 (11)0.0514 (4)
F100.0226 (3)1.11843 (13)−0.02764 (13)0.0575 (5)
F11−0.1963 (2)1.02734 (14)0.07661 (10)0.0519 (5)
F120.2087 (2)1.01509 (14)0.08206 (10)0.0505 (4)
Si10.50922 (10)0.78157 (5)0.27367 (5)0.0328 (2)
Si20.00000.50000.50000.0339 (2)
Si30.00001.00000.00000.0370 (3)
U11U22U33U12U13U23
C10.084 (2)0.0542 (19)0.0415 (16)−0.0097 (17)0.0083 (15)−0.0045 (14)
C20.081 (2)0.064 (2)0.0448 (17)−0.0093 (18)0.0126 (16)−0.0058 (15)
C30.128 (4)0.057 (2)0.0463 (19)−0.002 (2)0.007 (2)−0.0031 (16)
C40.118 (3)0.081 (3)0.050 (2)0.025 (2)0.005 (2)−0.0012 (19)
C50.105 (3)0.067 (2)0.0488 (19)0.016 (2)−0.0007 (19)−0.0104 (17)
C60.092 (3)0.0506 (19)0.0448 (17)−0.0089 (17)0.0047 (16)−0.0023 (14)
C70.073 (2)0.0411 (16)0.0428 (16)−0.0057 (14)0.0037 (14)0.0020 (12)
C80.076 (2)0.0458 (17)0.0431 (16)0.0089 (15)0.0005 (14)−0.0075 (13)
C90.074 (2)0.0551 (19)0.0367 (15)0.0095 (16)0.0021 (14)−0.0084 (13)
C100.0667 (19)0.0424 (16)0.0400 (15)−0.0072 (14)0.0086 (13)−0.0043 (12)
C110.068 (2)0.0513 (18)0.0378 (15)−0.0085 (15)0.0098 (13)−0.0074 (13)
C120.085 (2)0.060 (2)0.0407 (17)−0.0171 (18)0.0137 (16)−0.0115 (14)
N10.0343 (11)0.0477 (13)0.0284 (10)−0.0005 (9)0.0031 (8)0.0055 (9)
N20.0327 (11)0.0439 (12)0.0312 (10)0.0027 (9)0.0046 (8)0.0050 (9)
N30.0349 (11)0.0409 (12)0.0267 (10)0.0020 (9)0.0030 (8)0.0023 (8)
N40.0320 (10)0.0375 (11)0.0289 (10)0.0021 (8)0.0038 (8)0.0032 (8)
F10.0376 (8)0.0681 (11)0.0373 (8)0.0117 (7)0.0124 (6)0.0080 (7)
F20.0325 (8)0.0626 (10)0.0359 (8)0.0011 (7)−0.0024 (6)0.0082 (7)
F30.0435 (9)0.0435 (9)0.0799 (12)0.0011 (7)0.0045 (8)0.0161 (8)
F40.0340 (8)0.0681 (11)0.0431 (9)0.0119 (7)0.0149 (6)0.0189 (8)
F50.0363 (8)0.0857 (13)0.0454 (9)0.0008 (8)−0.0084 (7)0.0099 (9)
F60.0425 (9)0.0421 (9)0.0662 (11)0.0062 (7)0.0118 (7)0.0212 (8)
F70.0371 (8)0.0635 (11)0.0468 (9)0.0107 (7)0.0178 (7)0.0171 (8)
F80.0465 (9)0.0389 (9)0.0708 (11)0.0031 (7)0.0104 (8)0.0149 (8)
F90.0358 (8)0.0743 (12)0.0443 (9)−0.0001 (8)−0.0040 (7)0.0178 (8)
F100.0428 (9)0.0582 (11)0.0726 (12)−0.0008 (8)0.0034 (8)0.0268 (9)
F110.0351 (8)0.0858 (13)0.0366 (8)0.0119 (8)0.0090 (6)0.0158 (8)
F120.0311 (8)0.0823 (13)0.0380 (8)−0.0017 (8)−0.0052 (6)0.0121 (8)
Si10.0246 (3)0.0431 (4)0.0318 (4)0.0035 (3)0.0040 (3)0.0126 (3)
Si20.0250 (5)0.0411 (6)0.0368 (5)0.0039 (4)0.0067 (4)0.0142 (4)
Si30.0244 (5)0.0575 (7)0.0298 (5)0.0011 (4)0.0022 (4)0.0166 (4)
C1—N11.466 (4)C11—H11B0.9700
C1—C21.500 (4)C12—C12ii1.499 (6)
C1—H1A0.9700C12—H12A0.9700
C1—H1B0.9700C12—H12B0.9700
C2—C31.498 (5)N1—H1NB0.8900
C2—H2A0.9700N1—H1NA0.8900
C2—H2B0.9700N1—H1NC0.8900
C3—C41.527 (5)N2—H2NA0.8900
C3—H3A0.9700N2—H2NC0.8900
C3—H3B0.9700N2—H2NB0.8900
C4—C51.467 (5)N3—H3NA0.8900
C4—H4A0.9700N3—H3NB0.8900
C4—H4B0.9700N3—H3NC0.8900
C5—C61.499 (5)N4—H4NA0.8900
C5—H5A0.9700N4—H4NB0.8900
C5—H5B0.9700N4—H4NC0.8900
C6—N21.466 (4)F1—Si11.6794 (15)
C6—H6A0.9700F2—Si11.6837 (15)
C6—H6B0.9700F3—Si11.6798 (17)
C7—N31.478 (3)F4—Si11.6868 (15)
C7—C81.495 (4)F5—Si11.6677 (16)
C7—H7A0.9700F6—Si11.6915 (16)
C7—H7B0.9700F7—Si21.6848 (14)
C8—C91.507 (4)F8—Si21.6858 (16)
C8—H8A0.9700F9—Si21.6741 (15)
C8—H8B0.9700F10—Si31.6848 (17)
C9—C9i1.506 (5)F11—Si31.6830 (14)
C9—H9A0.9700F12—Si31.6759 (14)
C9—H9B0.9700Si2—F9iii1.6741 (15)
C10—N41.465 (3)Si2—F7iii1.6849 (14)
C10—C111.489 (4)Si2—F8iii1.6858 (16)
C10—H10A0.9700Si3—F12iv1.6760 (14)
C10—H10B0.9700Si3—F11iv1.6830 (14)
C11—C121.508 (4)Si3—F10iv1.6848 (17)
C11—H11A0.9700
N1—C1—C2112.6 (3)H12A—C12—H12B107.6
N1—C1—H1A109.1C1—N1—H1NB109.5
C2—C1—H1A109.1C1—N1—H1NA109.5
N1—C1—H1B109.1H1NB—N1—H1NA109.5
C2—C1—H1B109.1C1—N1—H1NC109.5
H1A—C1—H1B107.8H1NB—N1—H1NC109.5
C3—C2—C1112.9 (3)H1NA—N1—H1NC109.5
C3—C2—H2A109.0C6—N2—H2NA109.5
C1—C2—H2A109.0C6—N2—H2NC109.5
C3—C2—H2B109.0H2NA—N2—H2NC109.5
C1—C2—H2B109.0C6—N2—H2NB109.5
H2A—C2—H2B107.8H2NA—N2—H2NB109.5
C2—C3—C4115.1 (3)H2NC—N2—H2NB109.5
C2—C3—H3A108.5C7—N3—H3NA109.5
C4—C3—H3A108.5C7—N3—H3NB109.5
C2—C3—H3B108.5H3NA—N3—H3NB109.5
C4—C3—H3B108.5C7—N3—H3NC109.5
H3A—C3—H3B107.5H3NA—N3—H3NC109.5
C5—C4—C3116.0 (3)H3NB—N3—H3NC109.5
C5—C4—H4A108.3C10—N4—H4NA109.5
C3—C4—H4A108.3C10—N4—H4NB109.5
C5—C4—H4B108.3H4NA—N4—H4NB109.5
C3—C4—H4B108.3C10—N4—H4NC109.5
H4A—C4—H4B107.4H4NA—N4—H4NC109.5
C4—C5—C6117.4 (3)H4NB—N4—H4NC109.5
C4—C5—H5A108.0F5—Si1—F191.67 (8)
C6—C5—H5A108.0F5—Si1—F391.24 (10)
C4—C5—H5B108.0F1—Si1—F391.04 (9)
C6—C5—H5B108.0F5—Si1—F2179.11 (10)
H5A—C5—H5B107.2F1—Si1—F288.89 (8)
N2—C6—C5114.0 (3)F3—Si1—F289.43 (9)
N2—C6—H6A108.8F5—Si1—F489.45 (8)
C5—C6—H6A108.8F1—Si1—F4178.85 (9)
N2—C6—H6B108.8F3—Si1—F489.17 (9)
C5—C6—H6B108.8F2—Si1—F489.98 (8)
H6A—C6—H6B107.6F5—Si1—F688.99 (9)
N3—C7—C8112.4 (2)F1—Si1—F689.33 (8)
N3—C7—H7A109.1F3—Si1—F6179.56 (10)
C8—C7—H7A109.1F2—Si1—F690.33 (9)
N3—C7—H7B109.1F4—Si1—F690.46 (8)
C8—C7—H7B109.1F9iii—Si2—F9180.0
H7A—C7—H7B107.9F9iii—Si2—F789.15 (8)
C7—C8—C9115.8 (3)F9—Si2—F790.85 (8)
C7—C8—H8A108.3F9iii—Si2—F7iii90.85 (8)
C9—C8—H8A108.3F9—Si2—F7iii89.15 (8)
C7—C8—H8B108.3F7—Si2—F7iii180.0
C9—C8—H8B108.3F9iii—Si2—F890.78 (9)
H8A—C8—H8B107.4F9—Si2—F889.22 (9)
C9i—C9—C8112.9 (3)F7—Si2—F889.29 (8)
C9i—C9—H9A109.0F7iii—Si2—F890.71 (8)
C8—C9—H9A109.0F9iii—Si2—F8iii89.22 (9)
C9i—C9—H9B109.0F9—Si2—F8iii90.78 (9)
C8—C9—H9B109.0F7—Si2—F8iii90.71 (8)
H9A—C9—H9B107.8F7iii—Si2—F8iii89.29 (8)
N4—C10—C11112.4 (2)F8—Si2—F8iii180.0
N4—C10—H10A109.1F12—Si3—F12iv180.0
C11—C10—H10A109.1F12—Si3—F11iv89.08 (8)
N4—C10—H10B109.1F12iv—Si3—F11iv90.92 (8)
C11—C10—H10B109.1F12—Si3—F1190.92 (8)
H10A—C10—H10B107.8F12iv—Si3—F1189.08 (8)
C10—C11—C12113.3 (3)F11iv—Si3—F11180.000 (1)
C10—C11—H11A108.9F12—Si3—F10iv89.24 (9)
C12—C11—H11A108.9F12iv—Si3—F10iv90.76 (9)
C10—C11—H11B108.9F11iv—Si3—F10iv90.66 (9)
C12—C11—H11B108.9F11—Si3—F10iv89.34 (9)
H11A—C11—H11B107.7F12—Si3—F1090.76 (9)
C12ii—C12—C11114.8 (3)F12iv—Si3—F1089.24 (9)
C12ii—C12—H12A108.6F11iv—Si3—F1089.34 (9)
C11—C12—H12A108.6F11—Si3—F1090.66 (9)
C12ii—C12—H12B108.6F10iv—Si3—F10180.00 (12)
C11—C12—H12B108.6
D—H···AD—HH···AD···AD—H···A
N2—H2NC···F50.892.313.062 (3)142
N2—H2NC···F60.892.273.063 (3)148
N2—H2NB···F70.892.523.095 (3)123
N2—H2NB···F80.892.032.917 (3)175
N3—H3NA···F10.892.062.934 (3)169
N4—H4NA···F80.892.343.095 (3)143
N4—H4NA···F90.892.142.923 (3)146
N4—H4NC···F60.892.002.885 (3)172
N1—H1NB···F11i0.892.072.895 (3)155
N1—H1NA···F10v0.892.012.869 (3)163
N1—H1NC···F2vi0.892.022.857 (2)155
N2—H2NA···F7vii0.892.022.906 (3)170
N3—H3NB···F10iv0.892.483.239 (3)144
N3—H3NB···F120.892.132.907 (2)145
N3—H3NC···F3viii0.892.022.904 (3)170
N3—H3NC···F4viii0.892.443.034 (3)124
N4—H4NB···F4viii0.892.012.832 (3)154
N4—H4NB···F5viii0.892.513.086 (3)123
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
N2—H2NC⋯F50.892.313.062 (3)142
N2—H2NC⋯F60.892.273.063 (3)148
N2—H2NB⋯F70.892.523.095 (3)123
N2—H2NB⋯F80.892.032.917 (3)175
N3—H3NA⋯F10.892.062.934 (3)169
N4—H4NA⋯F80.892.343.095 (3)143
N4—H4NA⋯F90.892.142.923 (3)146
N4—H4NC⋯F60.892.002.885 (3)172
N1—H1NB⋯F11i 0.892.072.895 (3)155
N1—H1NA⋯F10iii 0.892.012.869 (3)163
N1—H1NC⋯F2ii 0.892.022.857 (2)155
N2—H2NA⋯F7iv 0.892.022.906 (3)170
N3—H3NB⋯F10v 0.892.483.239 (3)144
N3—H3NB⋯F120.892.132.907 (2)145
N3—H3NC⋯F3vi 0.892.022.904 (3)170
N3—H3NC⋯F4vi 0.892.443.034 (3)124
N4—H4NB⋯F4vi 0.892.012.832 (3)154
N4—H4NB⋯F5vi 0.892.513.086 (3)123

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

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20

3.  catena-Poly[heptyl-enedi-ammonium [[tetra-chloridobismuthate(III)]-μ-chlorido]].

Authors:  Ali Ouasri; Ali Rhandour; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-07-06
  3 in total
  2 in total

1.  Butane-1,4-di-ammonium hexa-fluoro-silicate.

Authors:  Ali Ouasri; Ali Rhandour; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-01-18

2.  Hydrogen bonds and van der Waals forces as tools for the construction of a herringbone pattern in the crystal structure of hexane-1,6-diaminium hexane-1,6-diyl bis-(hydrogen phospho-nate).

Authors:  Guido J Reiss; Martin van Megen; Walter Frank
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2017-01-01
  2 in total

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