Tetra­kis(3,5-dimethoxy­phen­yl)silane

The title compound, C₃₂H₃₆O₈Si, crystallizes from CH₂Cl₂ by slow evaporation to produce a close-packed structure. In this structure, the mol­ecules have crystallographic symmetry and no guest molecules are included. In contrast, crystallization of the closely related tetra­kis(3,5-dihydroxy­phen­yl)silane from a range of solvents is directed by phenolic hydrogen bonding to yield an open diamondoid network, which is filled by a combination of inter­penetration and inclusion of guests.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.149
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.72 mm

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: modified version of NRC-2/NRC2A (Ahmed et al., 1973); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Tetrakis(3,5-dimethoxyphenyl)silane

Crystal data

C32H36O8Si	Dx = 1.315 Mg m^−3
Mr = 576.70	Cu Kα radiation, λ = 1.5418 Å
Tetragonal, I41/a	Cell parameters from 25 reflections
Hall symbol: -I 4ad	θ = 20.0–22.5°
a = 17.230 (7) Å	µ = 1.14 mm^−1
c = 9.812 (4) Å	T = 292 K
V = 2913 (2) Å^3	Block, colorless
Z = 4	0.72 × 0.15 × 0.12 mm
F(000) = 1224

Data collection

Enraf–Nonius CAD-4 diffractometer	1138 reflections with I > 2σ(I)
Radiation source: X-ray sealed tube	Rint = 0.077
Graphite monochromator	θmax = 69.7°, θmin = 5.1°
ω/2θ scans	h = −21→21
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al., 1989)	k = −21→21
Tmin = 0.760, Tmax = 0.880	l = −11→11
10945 measured reflections	5 standard reflections every 60 min
1377 independent reflections	intensity decay: 0.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	All H-atom parameters refined
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.1051P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1377 reflections	Δρmax = 0.38 e Å^−3
130 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (3)

Special details

Experimental. X-ray crystallographic data for II were collected from a single-crystal sample, which was mounted on a glass fiber. Data were collected using an Enraf–Nonius CAD4 diffractometer equipped with FR590 generator, a Kappa goniometer, a standard scintillation counter and a locally modified low temperature device. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of 25 strong reflections. The intensity of some selected strong reflections was monitored during the course of the data collection. Data were corrected for absorption, Lorentz and polarization effect

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 13.3221 (0.0105) x + 6.3407 (0.0132) y + 5.0677 (0.0071) z = 2.0909 (0.0023) * 0.0040 (0.0014) C1 * -0.0073 (0.0014) C2 * 0.0038 (0.0015) C3 * 0.0031 (0.0015) C4 * -0.0066 (0.0014) C5 * 0.0030 (0.0014) C6 0.1277 (0.0027) Si 0.0177 (0.0031) O3 - 0.0480 (0.0029) O5 - 0.0978 (0.0049) C31 - 0.0949 (0.0044) C51 Rms deviation of fitted atoms = 0.0049

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 (Ų)

	x	y	z	Uiso*/Ueq
Si	0.0000	0.2500	0.1250	0.0331 (3)
O3	0.15623 (11)	−0.00610 (8)	0.01301 (19)	0.0578 (5)
O5	0.17764 (10)	0.19154 (9)	−0.30352 (17)	0.0508 (5)
C1	0.06290 (11)	0.18689 (10)	0.0142 (2)	0.0359 (5)
C2	0.08161 (12)	0.11174 (11)	0.0568 (2)	0.0398 (5)
H2	0.0601 (14)	0.0918 (14)	0.144 (3)	0.048 (6)*
C3	0.13314 (12)	0.06695 (11)	−0.0204 (2)	0.0401 (5)
C4	0.16448 (12)	0.09599 (12)	−0.1393 (2)	0.0418 (5)
H4	0.1976 (15)	0.0652 (14)	−0.186 (3)	0.048 (6)*
C5	0.14504 (11)	0.16987 (11)	−0.1825 (2)	0.0383 (5)
C6	0.09483 (11)	0.21584 (11)	−0.1062 (2)	0.0378 (5)
H6	0.0841 (14)	0.2685 (14)	−0.135 (2)	0.045 (6)*
C31	0.1215 (2)	−0.04219 (16)	0.1267 (4)	0.0673 (8)
H31A	0.1318 (19)	−0.0154 (18)	0.211 (3)	0.071 (9)*
H31B	0.1464 (19)	−0.0959 (19)	0.130 (3)	0.078 (9)*
H31C	0.0654 (19)	−0.0464 (16)	0.114 (3)	0.061 (8)*
C51	0.15877 (17)	0.26615 (15)	−0.3565 (3)	0.0573 (7)
H51A	0.1756 (18)	0.3049 (18)	−0.290 (3)	0.070 (9)*
H51B	0.100 (2)	0.267 (2)	−0.378 (4)	0.084 (10)*
H51C	0.191 (2)	0.275 (2)	−0.448 (4)	0.087 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si	0.0285 (4)	0.0285 (4)	0.0425 (6)	0.000	0.000	0.000
O3	0.0743 (11)	0.0314 (8)	0.0677 (12)	0.0145 (7)	0.0131 (8)	0.0084 (7)
O5	0.0584 (10)	0.0421 (8)	0.0519 (10)	0.0090 (7)	0.0136 (7)	0.0051 (7)
C1	0.0313 (9)	0.0315 (9)	0.0449 (11)	−0.0007 (7)	−0.0022 (7)	−0.0020 (8)
C2	0.0389 (10)	0.0323 (9)	0.0482 (12)	0.0018 (7)	0.0027 (9)	0.0013 (8)
C3	0.0413 (10)	0.0281 (9)	0.0509 (12)	0.0044 (7)	−0.0016 (9)	0.0007 (8)
C4	0.0393 (10)	0.0346 (10)	0.0516 (12)	0.0066 (8)	0.0038 (9)	−0.0035 (9)
C5	0.0356 (9)	0.0360 (10)	0.0433 (11)	0.0003 (7)	0.0014 (8)	−0.0008 (8)
C6	0.0359 (10)	0.0297 (9)	0.0478 (12)	0.0023 (7)	−0.0016 (8)	0.0011 (8)
C31	0.087 (2)	0.0383 (13)	0.077 (2)	0.0037 (13)	0.0108 (16)	0.0134 (12)
C51	0.0677 (16)	0.0436 (13)	0.0605 (16)	0.0051 (11)	0.0102 (12)	0.0122 (11)

Geometric parameters (Å, º)

Si—C1^i	1.881 (2)	C3—C4	1.379 (3)
Si—C1^ii	1.881 (2)	C4—C5	1.383 (3)
Si—C1^iii	1.881 (2)	C4—H4	0.91 (3)
Si—C1	1.881 (2)	C5—C6	1.392 (3)
O3—C3	1.360 (2)	C6—H6	0.97 (2)
O3—C31	1.410 (3)	C31—H31A	0.96 (3)
O5—C5	1.366 (2)	C31—H31B	1.02 (3)
O5—C51	1.424 (3)	C31—H31C	0.98 (3)
C1—C6	1.395 (3)	C51—H51A	0.98 (3)
C1—C2	1.398 (3)	C51—H51B	1.03 (3)
C2—C3	1.399 (3)	C51—H51C	1.07 (4)
C2—H2	1.00 (3)
C1^iii—Si—C1^i	109.38 (12)	C5—C4—H4	122.5 (17)
C1^iii—Si—C1^ii	109.52 (6)	O5—C5—C4	114.76 (17)
C1^i—Si—C1^ii	109.52 (6)	O5—C5—C6	124.62 (18)
C1^iii—Si—C1	109.52 (6)	C4—C5—C6	120.62 (19)
C1^i—Si—C1	109.52 (6)	C5—C6—C1	119.82 (18)
C1^ii—Si—C1	109.38 (12)	C5—C6—H6	119.7 (13)
C3—O3—C31	118.33 (19)	C1—C6—H6	120.5 (13)
C5—O5—C51	118.06 (17)	O3—C31—H31A	112.9 (19)
C6—C1—C2	119.57 (18)	O3—C31—H31B	104.3 (17)
C6—C1—Si	120.65 (14)	H31A—C31—H31B	109 (3)
C2—C1—Si	119.67 (15)	O3—C31—H31C	110.6 (17)
C1—C2—C3	119.66 (19)	H31A—C31—H31C	109 (3)
C1—C2—H2	119.4 (14)	H31B—C31—H31C	111 (2)
C3—C2—H2	120.8 (14)	O5—C51—H51A	107.7 (18)
O3—C3—C4	115.16 (18)	O5—C51—H51B	108 (2)
O3—C3—C2	124.4 (2)	H51A—C51—H51B	115 (3)
C4—C3—C2	120.41 (18)	O5—C51—H51C	108.5 (19)
C3—C4—C5	119.90 (18)	H51A—C51—H51C	108 (2)
C3—C4—H4	117.6 (17)	H51B—C51—H51C	110 (3)
C1^i—Si—C1—C6	−81.85 (12)	C1—C2—C3—C4	−1.1 (3)
C1^ii—Si—C1—C6	38.18 (13)	O3—C3—C4—C5	−179.82 (19)
C1^iii—Si—C1—C6	158.20 (16)	C2—C3—C4—C5	0.1 (3)
C1^i—Si—C1—C2	94.3 (2)	C51—O5—C5—C4	178.4 (2)
C1^ii—Si—C1—C2	−145.63 (18)	C51—O5—C5—C6	−0.5 (3)
C1^iii—Si—C1—C2	−25.60 (17)	C3—C4—C5—O5	−178.07 (18)
C6—C1—C2—C3	1.1 (3)	C3—C4—C5—C6	0.9 (3)
Si—C1—C2—C3	−175.13 (15)	O5—C5—C6—C1	177.98 (18)
C31—O3—C3—C4	−174.6 (2)	C4—C5—C6—C1	−0.9 (3)
C31—O3—C3—C2	5.5 (4)	C2—C1—C6—C5	−0.1 (3)
C1—C2—C3—O3	178.81 (19)	Si—C1—C6—C5	176.07 (14)

Symmetry codes: (i) −y+1/4, x+1/4, −z+1/4; (ii) −x, −y+1/2, z; (iii) y−1/4, −x+1/4, −z+1/4.