Bis[4-(2-iso­propyl-2H-tetra­zol-5-yl)phen­yl]di­methyl­silane

The title compound, C₂₂H₂₈N₈Si, has crystallographic 2 symmetry with the Si atom located on a twofold rotation axis. The tetra­zole ring is oriented at a dihedral angle of 5.32 (18)° with respect to the benzene ring. A C—H⋯π inter­action occurs between adjacent mol­ecules in the crystal structure.

Related literature

For applications of tetra­zole compounds, see: Bhandari et al. (2000). For the synthesis of tetra­zole derivatives, see: Demko & Sharpless (2001).

Experimental

Crystal data

• C₂₂H₂₈N₈Si

• M_r = 432.61

• Orthorhombic, P b c n

• a = 7.2722 (14) Å

• b = 11.536 (2) Å

• c = 28.444 (6) Å

• V = 2386.2 (8) ų

• Z = 4

• Mo Kα radiation

• μ = 0.12 mm⁻¹

• T = 298 K

• 0.46 × 0.37 × 0.07 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.945, T_max = 0.991

• 12923 measured reflections

• 2613 independent reflections

• 1827 reflections with I > 2σ(I)

• R_int = 0.049

Refinement

• R[F² > 2σ(F²)] = 0.088

• wR(F²) = 0.207

• S = 1.14

• 2613 reflections

• 144 parameters

• H-atom parameters constrained

• Δρ_max = 0.32 e Å⁻³

• Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the tetra­zole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cg^i	0.96	2.86	3.738 (5)	152
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

S1. Comment

Due to the application of tetrazoles in coordination chemistry, medicinal chemistry and material science (Bhandari et al., 2000), series of organic compounds with tetrazole group have been synthesized through different methods. Since a safe, convenient and envrironmentally friendly procedure for the synthesis of 5-substituted 1H-tetrazoles in water was reported by Demko and Sharpless (2001), synthesis of such compounds has been developed rapidly. However, due to the difficult in synthesis, tetrazole functional silane was never reported to our best knowledge. Here, we reported the synthesis and crystal structure of the title compound(I), namely, bis(4-(2-isopropyl-2H-tetrazol- 5-yl)phenyl)dimethylsilane.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The phenyl and tetrazole rings are not coplanar, and the two rings twisted to each other at a dihedral angle of 5.32 (18)°. The crystal packing is stablized by C—H···π interaction (Table 1).

Related literature

For applications of tetrazole compounds, see: Bhandari et al. (2000). For the synthesis of tetrazole derivatives, see: Demko & Sharpless (2001).

S2. Experimental

Tert-butyl lithium (4 mmol) in 3.08 ml n-pentane solution and 5-(4-bromophenyl)-2-isopropyl-2H-tetrazole (0.54 g, 2 mmol) were reacted at 195 K in 20 ml e ther. To the resulted solution was added dimethyldichlorosilane (0.13 g, 1 mmol), the solution was warmed slowly to room temperature and stirred overnight. Then the solution was filtered. The volatiles were removed from the resulting filtrate by vacuum distillation. The residue was purified by column chromatography using ethyl acetate/n-hexane as eluent to afford the pure compound. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation methanol solvent.

S3. Refinement

The H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and U_iso(H) = 1.5U_eq(C) for methyl and 1.2U_eq(C) for the others.

Computing details

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids.

Bis[4-(2-isopropyl-2H-tetrazol-5-yl)phenyl]dimethylsilane

Crystal data

C22H28N8Si	F(000) = 920
Mr = 432.61	Dx = 1.204 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1662 reflections
a = 7.2722 (14) Å	θ = 2.9–20.6°
b = 11.536 (2) Å	µ = 0.12 mm^−1
c = 28.444 (6) Å	T = 298 K
V = 2386.2 (8) Å^3	Plate, colourless
Z = 4	0.46 × 0.37 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2613 independent reflections
Radiation source: fine-focus sealed tube	1827 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ϕ and ω scans	θmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.945, Tmax = 0.991	k = −14→10
12923 measured reflections	l = −36→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.207	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0693P)^2 + 1.6746P] where P = (Fo^2 + 2Fc^2)/3
2613 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.19 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Si1	0.0000	0.80602 (11)	0.2500	0.0536 (4)
N1	0.5087 (4)	0.4553 (2)	0.40351 (9)	0.0610 (8)
N2	0.5050 (4)	0.3688 (2)	0.43454 (10)	0.0634 (8)
N3	0.3420 (5)	0.3270 (3)	0.44279 (12)	0.0804 (10)
N4	0.2291 (4)	0.3870 (3)	0.41648 (11)	0.0748 (9)
C1	0.1069 (4)	0.7079 (3)	0.29478 (10)	0.0473 (7)
C2	0.2904 (5)	0.7098 (3)	0.30746 (12)	0.0600 (9)
H2	0.3668	0.7655	0.2942	0.072*
C3	0.3639 (5)	0.6321 (3)	0.33902 (12)	0.0604 (9)
H3	0.4883	0.6361	0.3465	0.072*
C4	0.2560 (4)	0.5490 (3)	0.35956 (10)	0.0489 (8)
C5	0.0720 (5)	0.5455 (3)	0.34793 (12)	0.0679 (10)
H5	−0.0042	0.4903	0.3617	0.082*
C6	0.0004 (5)	0.6231 (3)	0.31617 (12)	0.0663 (10)
H6	−0.1239	0.6186	0.3087	0.080*
C7	0.3320 (5)	0.4640 (3)	0.39285 (10)	0.0512 (8)
C8	0.6736 (6)	0.3243 (3)	0.45759 (14)	0.0759 (11)
H8	0.6317	0.2726	0.4828	0.091*
C9	0.7768 (6)	0.4185 (4)	0.48099 (16)	0.0952 (15)
H9A	0.8732	0.3859	0.4999	0.143*
H9B	0.6949	0.4622	0.5007	0.143*
H9C	0.8292	0.4687	0.4576	0.143*
C10	0.7788 (6)	0.2512 (4)	0.42484 (17)	0.1005 (15)
H10A	0.6997	0.1925	0.4120	0.151*
H10B	0.8788	0.2151	0.4413	0.151*
H10C	0.8264	0.2982	0.3998	0.151*
C11	0.1814 (6)	0.8966 (3)	0.22270 (15)	0.0823 (13)
H11A	0.2715	0.8474	0.2082	0.123*
H11B	0.2394	0.9431	0.2464	0.123*
H11C	0.1273	0.9461	0.1994	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0603 (8)	0.0454 (7)	0.0552 (7)	0.000	−0.0171 (6)	0.000
N1	0.0659 (18)	0.0600 (18)	0.0569 (16)	0.0010 (15)	−0.0129 (14)	0.0044 (14)
N2	0.081 (2)	0.0553 (17)	0.0538 (16)	0.0102 (16)	−0.0108 (16)	0.0096 (13)
N3	0.084 (2)	0.080 (2)	0.078 (2)	−0.009 (2)	−0.0036 (19)	0.0279 (18)
N4	0.073 (2)	0.080 (2)	0.071 (2)	−0.0060 (17)	−0.0105 (17)	0.0253 (18)
C1	0.0533 (18)	0.0454 (17)	0.0431 (15)	−0.0011 (14)	−0.0056 (14)	−0.0048 (14)
C2	0.055 (2)	0.054 (2)	0.071 (2)	−0.0136 (16)	−0.0133 (17)	0.0106 (17)
C3	0.0481 (19)	0.063 (2)	0.070 (2)	−0.0021 (17)	−0.0174 (16)	0.0072 (18)
C4	0.0549 (18)	0.0506 (18)	0.0413 (15)	−0.0002 (14)	−0.0045 (14)	−0.0031 (14)
C5	0.058 (2)	0.079 (3)	0.066 (2)	−0.0155 (18)	−0.0068 (18)	0.021 (2)
C6	0.0496 (19)	0.084 (3)	0.065 (2)	−0.0095 (19)	−0.0155 (17)	0.0157 (19)
C7	0.061 (2)	0.0526 (19)	0.0403 (15)	0.0018 (15)	−0.0083 (15)	−0.0028 (15)
C8	0.090 (3)	0.071 (3)	0.067 (2)	0.014 (2)	−0.018 (2)	0.012 (2)
C9	0.105 (3)	0.078 (3)	0.103 (3)	0.013 (3)	−0.047 (3)	−0.014 (3)
C10	0.089 (3)	0.094 (3)	0.119 (4)	0.026 (3)	−0.008 (3)	−0.022 (3)
C11	0.088 (3)	0.073 (3)	0.085 (3)	−0.024 (2)	−0.025 (2)	0.028 (2)

Geometric parameters (Å, º)

Si1—C11	1.853 (4)	C4—C7	1.471 (4)
Si1—C11^i	1.853 (4)	C5—C6	1.374 (5)
Si1—C1^i	1.873 (3)	C5—H5	0.9300
Si1—C1	1.873 (3)	C6—H6	0.9300
N1—C7	1.324 (4)	C8—C10	1.471 (6)
N1—N2	1.332 (4)	C8—C9	1.479 (5)
N2—N3	1.301 (4)	C8—H8	0.9800
N2—C8	1.483 (4)	C9—H9A	0.9600
N3—N4	1.309 (4)	C9—H9B	0.9600
N4—C7	1.342 (4)	C9—H9C	0.9600
C1—C2	1.382 (4)	C10—H10A	0.9600
C1—C6	1.388 (4)	C10—H10B	0.9600
C2—C3	1.377 (4)	C10—H10C	0.9600
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.370 (4)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.379 (4)
C11—Si1—C11^i	111.4 (3)	C1—C6—H6	118.8
C11—Si1—C1^i	110.56 (16)	N1—C7—N4	112.1 (3)
C11^i—Si1—C1^i	109.28 (16)	N1—C7—C4	124.2 (3)
C11—Si1—C1	109.28 (16)	N4—C7—C4	123.6 (3)
C11^i—Si1—C1	110.56 (16)	C10—C8—C9	116.3 (4)
C1^i—Si1—C1	105.63 (19)	C10—C8—N2	110.4 (3)
C7—N1—N2	100.9 (3)	C9—C8—N2	111.3 (3)
N3—N2—N1	114.6 (3)	C10—C8—H8	106.0
N3—N2—C8	123.1 (3)	C9—C8—H8	106.0
N1—N2—C8	122.4 (3)	N2—C8—H8	106.0
N2—N3—N4	105.8 (3)	C8—C9—H9A	109.5
N3—N4—C7	106.6 (3)	C8—C9—H9B	109.5
C2—C1—C6	115.8 (3)	H9A—C9—H9B	109.5
C2—C1—Si1	124.7 (2)	C8—C9—H9C	109.5
C6—C1—Si1	119.5 (2)	H9A—C9—H9C	109.5
C3—C2—C1	122.4 (3)	H9B—C9—H9C	109.5
C3—C2—H2	118.8	C8—C10—H10A	109.5
C1—C2—H2	118.8	C8—C10—H10B	109.5
C4—C3—C2	120.7 (3)	H10A—C10—H10B	109.5
C4—C3—H3	119.6	C8—C10—H10C	109.5
C2—C3—H3	119.6	H10A—C10—H10C	109.5
C3—C4—C5	118.3 (3)	H10B—C10—H10C	109.5
C3—C4—C7	121.7 (3)	Si1—C11—H11A	109.5
C5—C4—C7	120.0 (3)	Si1—C11—H11B	109.5
C6—C5—C4	120.4 (3)	H11A—C11—H11B	109.5
C6—C5—H5	119.8	Si1—C11—H11C	109.5
C4—C5—H5	119.8	H11A—C11—H11C	109.5
C5—C6—C1	122.4 (3)	H11B—C11—H11C	109.5
C5—C6—H6	118.8
C7—N1—N2—N3	−0.1 (4)	C7—C4—C5—C6	−178.7 (3)
C7—N1—N2—C8	179.8 (3)	C4—C5—C6—C1	−0.5 (6)
N1—N2—N3—N4	0.0 (4)	C2—C1—C6—C5	−0.1 (5)
C8—N2—N3—N4	−180.0 (3)	Si1—C1—C6—C5	177.4 (3)
N2—N3—N4—C7	0.2 (4)	N2—N1—C7—N4	0.2 (4)
C11—Si1—C1—C2	4.3 (3)	N2—N1—C7—C4	179.4 (3)
C11^i—Si1—C1—C2	−118.6 (3)	N3—N4—C7—N1	−0.3 (4)
C1^i—Si1—C1—C2	123.2 (3)	N3—N4—C7—C4	−179.4 (3)
C11—Si1—C1—C6	−173.0 (3)	C3—C4—C7—N1	−4.4 (5)
C11^i—Si1—C1—C6	64.1 (3)	C5—C4—C7—N1	174.9 (3)
C1^i—Si1—C1—C6	−54.0 (2)	C3—C4—C7—N4	174.7 (3)
C6—C1—C2—C3	0.5 (5)	C5—C4—C7—N4	−6.0 (5)
Si1—C1—C2—C3	−176.9 (3)	N3—N2—C8—C10	103.6 (4)
C1—C2—C3—C4	−0.3 (5)	N1—N2—C8—C10	−76.3 (5)
C2—C3—C4—C5	−0.2 (5)	N3—N2—C8—C9	−125.6 (4)
C2—C3—C4—C7	179.1 (3)	N1—N2—C8—C9	54.4 (5)
C3—C4—C5—C6	0.6 (5)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the tetrazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cg^ii	0.96	2.86	3.738 (5)	152

Symmetry code: (ii) −x+1, −y+1, −z+1.