Hexane-1,6-di­ammonium hexa­fluoro­silicate

Ouasri, A.; Rhandour, A.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536813034144

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 1| January 2014| Pages o92-o93

https://doi.org/10.1107/S1600536813034144

Open

access

Hexane-1,6-diammonium hexafluorosilicate

Ali Ouasri,^a,^b ^* Ali Rhandour,^b Mohamed Saadi ^c and Lahcen El Ammari ^c

^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

(Received 13 December 2013; accepted 18 December 2013; online 24 December 2013)

The asymmetric unit of the title organic–inorganic molecular salt, C₆H₁₈N₂²⁺·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.

CCDC 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

C₆H₁₈N₂²⁺·SiF₆²⁻
M_r = 260.31
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.159
S = 1.06
4760 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯F10ⁱⁱⁱ	0.89	2.01	2.869 (3)	163
N1—H1NC⋯F2ⁱⁱ	0.89	2.02	2.857 (2)	155
N2—H2NA⋯F7^iv	0.89	2.02	2.906 (3)	170
N3—H3NB⋯F10^v	0.89	2.48	3.239 (3)	144
N3—H3NB⋯F12	0.89	2.13	2.907 (2)	145
N3—H3NC⋯F3^vi	0.89	2.02	2.904 (3)	170
N3—H3NC⋯F4^vi	0.89	2.44	3.034 (3)	124
N4—H4NB⋯F4^vi	0.89	2.01	2.832 (3)	154
N4—H4NB⋯F5^vi	0.89	2.51	3.086 (3)	123
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y, z+1; (iii) -x+1, -y+2, -z+1; (iv) -x+1, -y+1, -z+1; (v) -x, -y+2, -z; (vi) x-1, y, z.

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 ).

Supporting information

CCDC reference: 977855

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536813034144/rz5101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813034144/rz5101Isup2.hkl

checkCIF report

Comment top

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 SiF₆^2- octahedral geometry. The SiF₆^2- 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).

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top

	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).

Hexane-1,6-diammonium hexafluorosilicate top

Crystal data top

C₆H₁₈N₂²⁺·SiF₆²⁻	Z = 4
M_r = 260.31	F(000) = 544
Triclinic, P1	D_x = 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

Data collection top

Bruker X8 APEX diffractometer	4760 independent reflections
Radiation source: fine-focus sealed tube	3618 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 26.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
T_min = 0.686, T_max = 0.747	k = −17→17
29127 measured reflections	l = −18→18

Refinement top

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(F_o²) + (0.0734P)² + 1.0436P] where P = (F_o² + 2F_c²)/3
4760 reflections	(Δ/σ)_max < 0.001
274 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₆H₁₈N₂²⁺·SiF₆²⁻	γ = 90.906 (2)°
M_r = 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)°

Data collection top

Bruker X8 APEX diffractometer	4760 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3618 reflections with I > 2σ(I)
T_min = 0.686, T_max = 0.747	R_int = 0.023
29127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.06	Δρ_max = 0.46 e Å⁻³
4760 reflections	Δρ_min = −0.26 e Å⁻³
274 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—F12^iv	1.6760 (14)
C10—H10B	0.9700	Si3—F11^iv	1.6830 (14)
C11—C12	1.508 (4)	Si3—F10^iv	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—F12^iv	180.0
C11—C10—H10A	109.1	F12—Si3—F11^iv	89.08 (8)
N4—C10—H10B	109.1	F12^iv—Si3—F11^iv	90.92 (8)
C11—C10—H10B	109.1	F12—Si3—F11	90.92 (8)
H10A—C10—H10B	107.8	F12^iv—Si3—F11	89.08 (8)
C10—C11—C12	113.3 (3)	F11^iv—Si3—F11	180.000 (1)
C10—C11—H11A	108.9	F12—Si3—F10^iv	89.24 (9)
C12—C11—H11A	108.9	F12^iv—Si3—F10^iv	90.76 (9)
C10—C11—H11B	108.9	F11^iv—Si3—F10^iv	90.66 (9)
C12—C11—H11B	108.9	F11—Si3—F10^iv	89.34 (9)
H11A—C11—H11B	107.7	F12—Si3—F10	90.76 (9)
C12ⁱⁱ—C12—C11	114.8 (3)	F12^iv—Si3—F10	89.24 (9)
C12ⁱⁱ—C12—H12A	108.6	F11^iv—Si3—F10	89.34 (9)
C11—C12—H12A	108.6	F11—Si3—F10	90.66 (9)
C12ⁱⁱ—C12—H12B	108.6	F10^iv—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.

Hydrogen-bond geometry (Å, º) top

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···F10^v	0.89	2.01	2.869 (3)	163
N1—H1NC···F2^vi	0.89	2.02	2.857 (2)	155
N2—H2NA···F7^vii	0.89	2.02	2.906 (3)	170
N3—H3NB···F10^iv	0.89	2.48	3.239 (3)	144
N3—H3NB···F12	0.89	2.13	2.907 (2)	145
N3—H3NC···F3^viii	0.89	2.02	2.904 (3)	170
N3—H3NC···F4^viii	0.89	2.44	3.034 (3)	124
N4—H4NB···F4^viii	0.89	2.01	2.832 (3)	154
N4—H4NB···F5^viii	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.

Hydrogen-bond geometry (Å, º) top

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···F7^iv	0.89	2.02	2.906 (3)	170.4
N3—H3NB···F10^v	0.89	2.48	3.239 (3)	143.6
N3—H3NB···F12	0.89	2.13	2.907 (2)	145.3
N3—H3NC···F3^vi	0.89	2.02	2.904 (3)	170.3
N3—H3NC···F4^vi	0.89	2.44	3.034 (3)	124.1
N4—H4NB···F4^vi	0.89	2.01	2.832 (3)	153.7
N4—H4NB···F5^vi	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.

References

Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Elaoud, Z., Chaabouni, S., Daoud, A. & Kamoun, S. C. R. (1995). C. R. Acad. Sci. 320, 551–555. CAS Google Scholar
Elyoubi, M., Ouasri, A., Jeghnou, H., Rhandour, A., Dhamelincourt, M.-C., Dhamelincourt, P. & Mazzah, A. (2004). J. Raman Spectrosc. 35, 1056–1062. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jeghnou, H., Ouasri, A., Rhandour, A., Dhamelincourt, M. C., Dhamelincourt, P., Mazzah, A. & Roussel, P. (2005). J. Raman Spectrosc. 36, 1023–1028. Web of Science CrossRef CAS Google Scholar
Ouasri, A., Jeghnou, H., Rhandour, A., Mazzah, A. & Rousseau, P. (2012). J. Mol. Struct. 1028, 79–87. Web of Science CrossRef CAS Google Scholar
Ouasri, A., Jeghnou, H., Rhandour, A. & Roussel, P. (2013a). J. Solid State Chem. 200, 22–29. Web of Science CSD CrossRef CAS Google Scholar
Ouasri, A., Rhandour, A., Dhamelincourt, M. C., Dhamelincourt, P., Mazzah, A. & Taibi, M. (2003). Phase Transit. 76, 701–709. Web of Science CrossRef CAS Google Scholar
Ouasri, A., Rhandour, A., Saadi, M. & El Ammari, L. (2013b). Acta Cryst. E69, m437. CSD CrossRef IUCr Journals Google Scholar
Rhandour, A., Ouasri, A., Mazzah, A. & Rousseau, P. (2011). J. Mol. Struct. 990, 95–101. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar