1,8-Bis[3-(triethoxy­silyl)prop­yl]-1,8-diazo­niatricyclo­[9.3.1.14,8]hexa­decane diiodide

Rousselin, Y.; Denat, F.; Lebeau, B.; Walcarius, A.

doi:10.1107/S1600536809038112

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2531

doi:10.1107/S1600536809038112

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1,8-Bis[3-(triethoxysilyl)propyl]-1,8-diazoniatricyclo[9.3.1.1^4,8]hexadecane diiodide

Yoann Rousselin,^a ^* Franck Denat,^a Benedicte Lebeau ^b and Alain Walcarius ^c

^aICMUB, UMR5260, CNRS–Université de Bourgogne, 9 Avenue Alain Savary, 21078 Dijon Cedex, France, ^bLMPC, UMR 7016, CNRS–ENSCMu–UHA, 3 Rue A. Werner, 68093 Mulhouse cedex, France, and ^cLCPME, UMR 7564, CNRS–Nancy Université, 405 Rue de Vandoeuvre, 54600 Villers-les-Nancy, France
^*Correspondence e-mail: Yoann.Rousselin@u-bourgogne.fr

(Received 10 September 2009; accepted 21 September 2009; online 26 September 2009)

The organic molecule of title compound, C₃₀H₆₆N₄O₆Si₂²⁺·2I⁻, is located around a centre of symmetry. The structure exhibits disorder of the triethoxy groups with the ratios 0.78 (1)/0.22 (1), 0.67 (1)/0.33 (1) and 0.58 (1)/0.42 (1).

Related literature

For Si—O bond distances, see: Klapdohr et al. (2000 ); Bedford et al. (2001 ); Aksin et al. (2006 ).

Experimental

Crystal data

C₃₀H₆₆N₄O₆Si₂²⁺·2I⁻
M_r = 888.85
Monoclinic, P 2₁ /c
a = 15.0484 (2) Å
b = 8.4229 (1) Å
c = 16.5921 (3) Å
β = 101.808 (1)°
V = 2058.57 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.63 mm⁻¹
T = 115 K
0.21 × 0.21 × 0.15 mm

Data collection

Nonius Kappa CCD diffractometer
Absorption correction: none
8944 measured reflections
4686 independent reflections
3900 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.076
S = 1.03
4686 reflections
208 parameters
17 restraints
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038112/rk2168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038112/rk2168Isup2.hkl

checkCIF report

Comment top

The molecule of title compound, C₃₀H₆₆N₄O₆Si₂^.2(I), placed around of centre of symmetry. The Si—O bond distances (Si1—O1 = 1.615 (2), Si1—O2B = 1.629 (7), Si1—O2A = 1.633 (4), Si1—O3A = 1.635 (5), Si1—O3B = 1.644 (6) Å) are in good agreement with those observed in literature - Klapdohr et al., (2000); Bedford et al., (2001); Aksin et al., (2006) - Si—O = 1.611 (10)–1.644 (12)Å. The molecular structure shows a trans–conformation for the two methylenic bridge (Fig. 1).

Related literature top

For Si—O bond distances, see: Klapdohr et al. (2000); Bedford et al. (2001); Aksin et al. (2006).

Experimental top

The 59.5 g of iodopropyltriethoxysilane (2 eq., 0.18 mol) were added to a solution of formaldehyde–cyclam (purchased from CheMatech) (20.07 g, 0.09 mol) in freshly distilled acetonitrile (180 ml) under N₂. The white precipitate formed after 3 h was filtered, rinsed with acetonitrile (50 ml). The resulting solid was dried under vacuum. The title compound, I, was obtained as a white solid (m = 42.74 g, 46.5 mmol, yield = 51.6%). No trace of cis–disubstituted macrocycle was detected, indicating a strong selectivity for the trans–disubstitution. Crystals of I suitable for single–crystal X–ray diffraction were selected directly from the sample.

¹³C [¹H] NMR (75 MHz, CDCl₃, 300 K): (CH₂) 7.2, 15.2, (CH₃) 18.7, (CH₂) 19.6, 46.8, 46.9, 51.3, (O–CH₂) 58.4, (CH₂) 59.2, 60.8, 77.0. MALDI–TOF: m/z = 635.02 [M⁺].

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular view of I with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity. Only major molecular moieties for disordered parts are shown. Symmetry codes: (i) -x+1, -y, -z.

1,8-Bis[3-(triethoxysilyl)propyl]-1,8-diazoniatricyclo[9.3.1.1^4,8]hexadecane diiodide top

Crystal data top

C₃₀H₆₆N₄O₆Si₂²⁺·2I⁻	F(000) = 912
M_r = 888.85	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4978 reflections
a = 15.0484 (2) Å	θ = 1.0–27.5°
b = 8.4229 (1) Å	µ = 1.63 mm⁻¹
c = 16.5921 (3) Å	T = 115 K
β = 101.808 (1)°	Prism, colourless
V = 2058.57 (5) Å³	0.21 × 0.21 × 0.15 mm
Z = 2

Data collection top

Nonius Kappa CCD diffractometer	3900 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 2.9°
Detector resolution: 9 pixels mm^-1	h = −19→19
ϕ and ω scans	k = −10→10
8944 measured reflections	l = −21→21
4686 independent reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0349P)² + 1.6474P] where P = (F_o² + 2F_c²)/3
4686 reflections	(Δ/σ)_max = 0.002
208 parameters	Δρ_max = 0.80 e Å⁻³
17 restraints	Δρ_min = −0.84 e Å⁻³
16 constraints

Crystal data top

C₃₀H₆₆N₄O₆Si₂²⁺·2I⁻	V = 2058.57 (5) Å³
M_r = 888.85	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.0484 (2) Å	µ = 1.63 mm⁻¹
b = 8.4229 (1) Å	T = 115 K
c = 16.5921 (3) Å	0.21 × 0.21 × 0.15 mm
β = 101.808 (1)°

Data collection top

Nonius Kappa CCD diffractometer	3900 reflections with I > 2σ(I)
8944 measured reflections	R_int = 0.030
4686 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	17 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.03	Δρ_max = 0.80 e Å⁻³
4686 reflections	Δρ_min = −0.84 e Å⁻³
208 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
C1	0.59893 (17)	0.0563 (3)	0.11258 (14)	0.0219 (5)
H1A	0.5638	−0.0392	0.1215	0.026*
H1B	0.6450	0.0741	0.1636	0.026*
C2	0.64831 (17)	0.0206 (3)	0.04340 (14)	0.0231 (5)
H2A	0.6804	0.1179	0.0318	0.028*
H2B	0.6949	−0.0616	0.0627	0.028*
C3	0.64235 (18)	−0.0542 (3)	−0.09955 (16)	0.0275 (6)
H3A	0.6837	−0.1465	−0.0873	0.033*
H3B	0.6793	0.0417	−0.1032	0.033*
C4	0.5753 (2)	−0.0802 (3)	−0.18030 (15)	0.0289 (6)
H4A	0.5414	0.0195	−0.1962	0.035*
H4B	0.6093	−0.1057	−0.2238	0.035*
C5	0.50826 (18)	−0.2128 (3)	−0.17557 (14)	0.0244 (5)
H5A	0.5400	−0.3162	−0.1734	0.029*
H5B	0.4599	−0.2113	−0.2260	0.029*
C6	0.54212 (16)	−0.1799 (3)	−0.02599 (13)	0.0192 (5)
H6A	0.5175	−0.1772	0.0250	0.023*
H6B	0.5839	−0.2715	−0.0227	0.023*
C7	0.58228 (17)	0.3514 (3)	0.08780 (14)	0.0214 (5)
H7A	0.5970	0.3490	0.0323	0.026*
H7B	0.5389	0.4396	0.0884	0.026*
C8	0.66860 (17)	0.3891 (3)	0.14980 (15)	0.0232 (5)
H8A	0.7175	0.3148	0.1428	0.028*
H8B	0.6581	0.3774	0.2065	0.028*
C9	0.69656 (17)	0.5607 (3)	0.13546 (15)	0.0241 (5)
H9A	0.6483	0.6334	0.1457	0.029*
H9B	0.7009	0.5726	0.0770	0.029*
Si1	0.80597 (5)	0.62166 (9)	0.20138 (5)	0.02915 (17)
O1	0.81232 (14)	0.5729 (2)	0.29651 (11)	0.0361 (5)
C11A	0.8556 (3)	0.4338 (5)	0.3373 (2)	0.0469 (7)	0.78
H11A	0.9028	0.3950	0.3084	0.056*	0.78
H11B	0.8103	0.3484	0.3366	0.056*	0.78
C12A	0.8981 (3)	0.4762 (6)	0.4245 (2)	0.0469 (7)	0.78
H12A	0.9275	0.3821	0.4530	0.070*	0.78
H12B	0.8510	0.5143	0.4528	0.070*	0.78
H12C	0.9434	0.5598	0.4248	0.070*	0.78
O2A	0.8055 (5)	0.8155 (4)	0.1990 (3)	0.0331 (13)	0.67
C21A	0.8750 (5)	0.9184 (6)	0.2443 (4)	0.0513 (14)	0.67
H21A	0.9327	0.8592	0.2608	0.062*	0.67
H21B	0.8567	0.9577	0.2947	0.062*	0.67
C22A	0.8879 (5)	1.0565 (6)	0.1897 (4)	0.0513 (14)	0.67
H22A	0.9363	1.1256	0.2190	0.077*	0.67
H22B	0.8312	1.1169	0.1754	0.077*	0.67
H22C	0.9045	1.0165	0.1393	0.077*	0.67
O3A	0.8982 (4)	0.5450 (14)	0.1800 (4)	0.0372 (16)	0.58
C31A	0.9148 (5)	0.5705 (8)	0.0983 (4)	0.0554 (10)	0.58
H31A	0.9762	0.6158	0.1020	0.066*	0.58
H31B	0.8699	0.6470	0.0683	0.066*	0.58
C32A	0.9074 (5)	0.4163 (7)	0.0524 (4)	0.0554 (10)	0.58
H32A	0.9235	0.4327	−0.0013	0.083*	0.58
H32B	0.8450	0.3767	0.0444	0.083*	0.58
H32C	0.9489	0.3386	0.0841	0.083*	0.58
C11B	0.8814 (9)	0.5688 (15)	0.3700 (7)	0.0469 (7)	0.22
H11C	0.8631	0.6319	0.4143	0.056*	0.22
H11D	0.9394	0.6111	0.3596	0.056*	0.22
C12B	0.8901 (12)	0.3975 (16)	0.3927 (10)	0.0469 (7)	0.22
H12D	0.9334	0.3855	0.4452	0.070*	0.22
H12E	0.9121	0.3384	0.3497	0.070*	0.22
H12F	0.8308	0.3560	0.3981	0.070*	0.22
O2B	0.8147 (12)	0.8091 (9)	0.1799 (8)	0.0331 (13)	0.33
C21B	0.8921 (11)	0.8929 (11)	0.2268 (11)	0.0513 (14)	0.33
H21C	0.9471	0.8657	0.2056	0.062*	0.33
H21D	0.9022	0.8599	0.2853	0.062*	0.33
C22B	0.8762 (11)	1.0688 (11)	0.2205 (8)	0.0513 (14)	0.33
H22D	0.9308	1.1245	0.2490	0.077*	0.33
H22E	0.8250	1.0965	0.2459	0.077*	0.33
H22F	0.8625	1.1002	0.1624	0.077*	0.33
O3B	0.8823 (7)	0.521 (2)	0.1642 (6)	0.0372 (16)	0.42
C31B	0.8901 (7)	0.4696 (11)	0.0824 (5)	0.0554 (10)	0.42
H31C	0.8350	0.4095	0.0568	0.066*	0.42
H31D	0.9431	0.3982	0.0866	0.066*	0.42
C32B	0.9010 (6)	0.6094 (10)	0.0298 (5)	0.0554 (10)	0.42
H32D	0.9007	0.5734	−0.0264	0.083*	0.42
H32E	0.9588	0.6625	0.0522	0.083*	0.42
H32F	0.8509	0.6839	0.0291	0.083*	0.42
N1	0.53482 (13)	0.1971 (2)	0.10041 (11)	0.0190 (4)
N2	0.59027 (13)	−0.0345 (3)	−0.03396 (11)	0.0205 (4)
I1	0.660451 (12)	0.40929 (2)	−0.121474 (10)	0.03066 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0257 (13)	0.0179 (12)	0.0204 (11)	0.0039 (10)	0.0006 (9)	0.0014 (9)
C2	0.0217 (12)	0.0210 (13)	0.0261 (12)	0.0012 (10)	0.0039 (10)	−0.0022 (10)
C3	0.0302 (14)	0.0256 (14)	0.0310 (13)	−0.0024 (11)	0.0161 (11)	−0.0011 (11)
C4	0.0406 (16)	0.0270 (14)	0.0229 (12)	−0.0020 (12)	0.0151 (11)	0.0014 (10)
C5	0.0343 (14)	0.0242 (13)	0.0164 (11)	0.0024 (11)	0.0094 (10)	−0.0012 (10)
C6	0.0202 (12)	0.0190 (12)	0.0178 (10)	0.0016 (9)	0.0027 (9)	0.0005 (9)
C7	0.0270 (13)	0.0158 (11)	0.0208 (11)	−0.0001 (10)	0.0035 (9)	0.0001 (9)
C8	0.0238 (13)	0.0221 (13)	0.0232 (12)	0.0016 (10)	0.0038 (10)	−0.0015 (10)
C9	0.0248 (13)	0.0246 (13)	0.0233 (12)	−0.0007 (10)	0.0062 (10)	−0.0002 (10)
Si1	0.0226 (4)	0.0339 (4)	0.0295 (4)	−0.0054 (3)	0.0018 (3)	0.0045 (3)
O1	0.0393 (12)	0.0396 (12)	0.0270 (10)	0.0019 (9)	0.0011 (8)	0.0013 (8)
C11A	0.0436 (16)	0.056 (2)	0.0373 (16)	0.0062 (15)	−0.0013 (13)	0.0084 (13)
C12A	0.0436 (16)	0.056 (2)	0.0373 (16)	0.0062 (15)	−0.0013 (13)	0.0084 (13)
O2A	0.036 (2)	0.0343 (12)	0.026 (3)	−0.0153 (11)	−0.001 (2)	0.0030 (13)
C21A	0.044 (3)	0.0352 (16)	0.066 (3)	−0.0109 (14)	−0.009 (2)	−0.0051 (17)
C22A	0.044 (3)	0.0352 (16)	0.066 (3)	−0.0109 (14)	−0.009 (2)	−0.0051 (17)
O3A	0.013 (2)	0.066 (4)	0.030 (3)	−0.004 (3)	−0.002 (2)	0.002 (2)
C31A	0.047 (2)	0.076 (3)	0.050 (2)	−0.005 (2)	0.0256 (18)	−0.001 (2)
C32A	0.047 (2)	0.076 (3)	0.050 (2)	−0.005 (2)	0.0256 (18)	−0.001 (2)
C11B	0.0436 (16)	0.056 (2)	0.0373 (16)	0.0062 (15)	−0.0013 (13)	0.0084 (13)
C12B	0.0436 (16)	0.056 (2)	0.0373 (16)	0.0062 (15)	−0.0013 (13)	0.0084 (13)
O2B	0.036 (2)	0.0343 (12)	0.026 (3)	−0.0153 (11)	−0.001 (2)	0.0030 (13)
C21B	0.044 (3)	0.0352 (16)	0.066 (3)	−0.0109 (14)	−0.009 (2)	−0.0051 (17)
C22B	0.044 (3)	0.0352 (16)	0.066 (3)	−0.0109 (14)	−0.009 (2)	−0.0051 (17)
O3B	0.013 (2)	0.066 (4)	0.030 (3)	−0.004 (3)	−0.002 (2)	0.002 (2)
C31B	0.047 (2)	0.076 (3)	0.050 (2)	−0.005 (2)	0.0256 (18)	−0.001 (2)
C32B	0.047 (2)	0.076 (3)	0.050 (2)	−0.005 (2)	0.0256 (18)	−0.001 (2)
N1	0.0221 (10)	0.0184 (10)	0.0164 (9)	0.0012 (8)	0.0039 (8)	0.0008 (8)
N2	0.0217 (11)	0.0202 (10)	0.0200 (9)	−0.0016 (8)	0.0051 (8)	−0.0024 (8)
I1	0.03902 (12)	0.02923 (11)	0.02399 (10)	0.00690 (8)	0.00707 (7)	0.00048 (7)

Geometric parameters (Å, º) top

C1—N1	1.516 (3)	C11A—H11B	0.9900
C1—C2	1.520 (3)	C12A—H12A	0.9800
C1—H1A	0.9900	C12A—H12B	0.9800
C1—H1B	0.9900	C12A—H12C	0.9800
C2—N2	1.472 (3)	O2A—C21A	1.446 (5)
C2—H2A	0.9900	C21A—C22A	1.510 (6)
C2—H2B	0.9900	C21A—H21A	0.9900
C3—N2	1.475 (3)	C21A—H21B	0.9900
C3—C4	1.519 (4)	C22A—H22A	0.9800
C3—H3A	0.9900	C22A—H22B	0.9800
C3—H3B	0.9900	C22A—H22C	0.9800
C4—C5	1.518 (4)	O3A—C31A	1.444 (7)
C4—H4A	0.9900	C31A—C32A	1.498 (6)
C4—H4B	0.9900	C31A—H31A	0.9900
C5—N1ⁱ	1.524 (3)	C31A—H31B	0.9900
C5—H5A	0.9900	C32A—H32A	0.9800
C5—H5B	0.9900	C32A—H32B	0.9800
C6—N2	1.443 (3)	C32A—H32C	0.9800
C6—N1ⁱ	1.517 (3)	C11B—C12B	1.490 (8)
C6—H6A	0.9900	C11B—H11C	0.9900
C6—H6B	0.9900	C11B—H11D	0.9900
C7—C8	1.516 (3)	C12B—H12D	0.9800
C7—N1	1.518 (3)	C12B—H12E	0.9800
C7—H7A	0.9900	C12B—H12F	0.9800
C7—H7B	0.9900	O2B—C21B	1.446 (7)
C8—C9	1.538 (3)	C21B—C22B	1.501 (8)
C8—H8A	0.9900	C21B—H21C	0.9900
C8—H8B	0.9900	C21B—H21D	0.9900
C9—Si1	1.853 (3)	C22B—H22D	0.9800
C9—H9A	0.9900	C22B—H22E	0.9800
C9—H9B	0.9900	C22B—H22F	0.9800
Si1—O1	1.6148 (19)	O3B—C31B	1.452 (7)
Si1—O2B	1.629 (7)	C31B—C32B	1.495 (7)
Si1—O2A	1.633 (4)	C31B—H31C	0.9900
Si1—O3A	1.635 (5)	C31B—H31D	0.9900
Si1—O3B	1.644 (6)	C32B—H32D	0.9800
O1—C11B	1.431 (7)	C32B—H32E	0.9800
O1—C11A	1.441 (4)	C32B—H32F	0.9800
C11A—C12A	1.500 (5)	N1—C6ⁱ	1.517 (3)
C11A—H11A	0.9900	N1—C5ⁱ	1.524 (3)

N1—C1—C2	116.77 (19)	H12A—C12A—H12B	109.5
N1—C1—H1A	108.1	C11A—C12A—H12C	109.5
C2—C1—H1A	108.1	H12A—C12A—H12C	109.5
N1—C1—H1B	108.1	H12B—C12A—H12C	109.5
C2—C1—H1B	108.1	C21A—O2A—Si1	126.0 (5)
H1A—C1—H1B	107.3	O2A—C21A—C22A	108.5 (5)
N2—C2—C1	115.2 (2)	O2A—C21A—H21A	110.0
N2—C2—H2A	108.5	C22A—C21A—H21A	110.0
C1—C2—H2A	108.5	O2A—C21A—H21B	110.0
N2—C2—H2B	108.5	C22A—C21A—H21B	110.0
C1—C2—H2B	108.5	H21A—C21A—H21B	108.4
H2A—C2—H2B	107.5	C21A—C22A—H22A	109.5
N2—C3—C4	108.1 (2)	C21A—C22A—H22B	109.5
N2—C3—H3A	110.1	H22A—C22A—H22B	109.5
C4—C3—H3A	110.1	C21A—C22A—H22C	109.5
N2—C3—H3B	110.1	H22A—C22A—H22C	109.5
C4—C3—H3B	110.1	H22B—C22A—H22C	109.5
H3A—C3—H3B	108.4	C31A—O3A—Si1	117.6 (6)
C5—C4—C3	112.9 (2)	O3A—C31A—C32A	109.8 (6)
C5—C4—H4A	109.0	O3A—C31A—H31A	109.7
C3—C4—H4A	109.0	C32A—C31A—H31A	109.7
C5—C4—H4B	109.0	O3A—C31A—H31B	109.7
C3—C4—H4B	109.0	C32A—C31A—H31B	109.7
H4A—C4—H4B	107.8	H31A—C31A—H31B	108.2
C4—C5—N1ⁱ	112.17 (19)	C31A—C32A—H32A	109.5
C4—C5—H5A	109.2	C31A—C32A—H32B	109.5
N1ⁱ—C5—H5A	109.2	H32A—C32A—H32B	109.5
C4—C5—H5B	109.2	C31A—C32A—H32C	109.5
N1ⁱ—C5—H5B	109.2	H32A—C32A—H32C	109.5
H5A—C5—H5B	107.9	H32B—C32A—H32C	109.5
N2—C6—N1ⁱ	108.71 (17)	O1—C11B—C12B	104.5 (9)
N2—C6—H6A	109.9	O1—C11B—H11C	110.9
N1ⁱ—C6—H6A	109.9	C12B—C11B—H11C	110.9
N2—C6—H6B	109.9	O1—C11B—H11D	110.9
N1ⁱ—C6—H6B	109.9	C12B—C11B—H11D	110.9
H6A—C6—H6B	108.3	H11C—C11B—H11D	108.9
C8—C7—N1	116.57 (19)	C11B—C12B—H12D	109.5
C8—C7—H7A	108.1	C11B—C12B—H12E	109.5
N1—C7—H7A	108.1	H12D—C12B—H12E	109.5
C8—C7—H7B	108.1	C11B—C12B—H12F	109.5
N1—C7—H7B	108.1	H12D—C12B—H12F	109.5
H7A—C7—H7B	107.3	H12E—C12B—H12F	109.5
C7—C8—C9	108.4 (2)	C21B—O2B—Si1	116.6 (9)
C7—C8—H8A	110.0	O2B—C21B—C22B	110.2 (11)
C9—C8—H8A	110.0	O2B—C21B—H21C	109.6
C7—C8—H8B	110.0	C22B—C21B—H21C	109.6
C9—C8—H8B	110.0	O2B—C21B—H21D	109.6
H8A—C8—H8B	108.4	C22B—C21B—H21D	109.6
C8—C9—Si1	114.03 (18)	H21C—C21B—H21D	108.1
C8—C9—H9A	108.7	C21B—C22B—H22D	109.5
Si1—C9—H9A	108.7	C21B—C22B—H22E	109.5
C8—C9—H9B	108.7	H22D—C22B—H22E	109.5
Si1—C9—H9B	108.7	C21B—C22B—H22F	109.5
H9A—C9—H9B	107.6	H22D—C22B—H22F	109.5
O1—Si1—O2B	117.9 (5)	H22E—C22B—H22F	109.5
O1—Si1—O2A	106.10 (19)	C31B—O3B—Si1	134.5 (8)
O1—Si1—O3A	103.2 (3)	O3B—C31B—C32B	110.4 (11)
O2B—Si1—O3A	103.0 (8)	O3B—C31B—H31C	109.6
O2A—Si1—O3A	112.9 (5)	C32B—C31B—H31C	109.6
O1—Si1—O3B	109.3 (5)	O3B—C31B—H31D	109.6
O2B—Si1—O3B	108.8 (9)	C32B—C31B—H31D	109.6
O2A—Si1—O3B	120.3 (7)	H31C—C31B—H31D	108.1
O1—Si1—C9	111.97 (11)	C31B—C32B—H32D	109.5
O2B—Si1—C9	103.9 (6)	C31B—C32B—H32E	109.5
O2A—Si1—C9	105.3 (3)	H32D—C32B—H32E	109.5
O3A—Si1—C9	117.0 (3)	C31B—C32B—H32F	109.5
O3B—Si1—C9	103.9 (4)	H32D—C32B—H32F	109.5
C11B—O1—C11A	53.1 (5)	H32E—C32B—H32F	109.5
C11B—O1—Si1	136.6 (7)	C1—N1—C6ⁱ	113.09 (17)
C11A—O1—Si1	126.6 (2)	C1—N1—C7	112.57 (18)
O1—C11A—C12A	108.8 (3)	C6ⁱ—N1—C7	105.79 (17)
O1—C11A—H11A	109.9	C1—N1—C5ⁱ	108.91 (17)
C12A—C11A—H11A	109.9	C6ⁱ—N1—C5ⁱ	107.02 (17)
O1—C11A—H11B	109.9	C7—N1—C5ⁱ	109.24 (18)
C12A—C11A—H11B	109.9	C6—N2—C2	114.02 (18)
H11A—C11A—H11B	108.3	C6—N2—C3	108.95 (19)
C11A—C12A—H12A	109.5	C2—N2—C3	111.64 (19)
C11A—C12A—H12B	109.5

N1—C1—C2—N2	−67.5 (3)	O2A—Si1—O3A—C31A	−64.5 (8)
N2—C3—C4—C5	−52.3 (3)	O3B—Si1—O3A—C31A	62 (4)
C3—C4—C5—N1ⁱ	48.6 (3)	C9—Si1—O3A—C31A	57.9 (9)
N1—C7—C8—C9	−170.30 (19)	Si1—O3A—C31A—C32A	−112.4 (8)
C7—C8—C9—Si1	−175.74 (16)	C11A—O1—C11B—C12B	−9.4 (8)
C8—C9—Si1—O1	−46.8 (2)	Si1—O1—C11B—C12B	−116.4 (10)
C8—C9—Si1—O2B	−175.2 (6)	O1—Si1—O2B—C21B	51.5 (14)
C8—C9—Si1—O2A	−161.7 (2)	O2A—Si1—O2B—C21B	79 (4)
C8—C9—Si1—O3A	72.0 (5)	O3A—Si1—O2B—C21B	−61.4 (13)
C8—C9—Si1—O3B	71.0 (6)	O3B—Si1—O2B—C21B	−73.6 (13)
O2B—Si1—O1—C11B	−70.0 (11)	C9—Si1—O2B—C21B	176.1 (11)
O2A—Si1—O1—C11B	−76.2 (9)	Si1—O2B—C21B—C22B	−162.0 (13)
O3A—Si1—O1—C11B	42.7 (9)	O1—Si1—O3B—C31B	154.0 (16)
O3B—Si1—O1—C11B	54.8 (10)	O2B—Si1—O3B—C31B	−76.0 (19)
C9—Si1—O1—C11B	169.4 (8)	O2A—Si1—O3B—C31B	−83.0 (18)
O2B—Si1—O1—C11A	−142.4 (8)	O3A—Si1—O3B—C31B	−142 (6)
O2A—Si1—O1—C11A	−148.7 (4)	C9—Si1—O3B—C31B	34.3 (19)
O3A—Si1—O1—C11A	−29.7 (5)	Si1—O3B—C31B—C32B	67.1 (19)
O3B—Si1—O1—C11A	−17.6 (7)	C2—C1—N1—C6ⁱ	60.8 (3)
C9—Si1—O1—C11A	97.0 (3)	C2—C1—N1—C7	−59.0 (3)
C11B—O1—C11A—C12A	19.5 (9)	C2—C1—N1—C5ⁱ	179.6 (2)
Si1—O1—C11A—C12A	144.5 (3)	C8—C7—N1—C1	−49.9 (3)
O1—Si1—O2A—C21A	58.1 (6)	C8—C7—N1—C6ⁱ	−173.89 (19)
O2B—Si1—O2A—C21A	−97 (4)	C8—C7—N1—C5ⁱ	71.2 (3)
O3A—Si1—O2A—C21A	−54.2 (6)	N1ⁱ—C6—N2—C2	162.99 (18)
O3B—Si1—O2A—C21A	−66.3 (7)	N1ⁱ—C6—N2—C3	−71.6 (2)
C9—Si1—O2A—C21A	177.0 (5)	C1—C2—N2—C6	−60.5 (3)
Si1—O2A—C21A—C22A	141.1 (5)	C1—C2—N2—C3	175.5 (2)
O1—Si1—O3A—C31A	−178.7 (7)	C4—C3—N2—C6	63.8 (3)
O2B—Si1—O3A—C31A	−55.4 (9)	C4—C3—N2—C2	−169.4 (2)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₃₀H₆₆N₄O₆Si₂²⁺·2I⁻
M_r	888.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	115
a, b, c (Å)	15.0484 (2), 8.4229 (1), 16.5921 (3)
β (°)	101.808 (1)
V (Å³)	2058.57 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.63
Crystal size (mm)	0.21 × 0.21 × 0.15

Data collection
Diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8944, 4686, 3900
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.076, 1.03
No. of reflections	4686
No. of parameters	208
No. of restraints	17
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.84

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

This work was supported by the French National Research Agency (project No. NT05 3 41602 mesoporelect), the Centre National de la Recherche Scientifique (CNRS), the Ministère de l'Enseignement Supérieur de la Recherche and the Conseil Régional de Bourgogne.

References

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