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The title compound, C32H40N2O3Si3 or (Ph2SiO)2OSi(NH-tBu)2, was synthesized by the in situ reaction of [Ph2Si(OH)]2O with two equivalents of nBuLi, followed by the addition of Cl2Si(NH-tBu)2. The addition of tert-butyl­amide substituents to one of the Si centres causes a slight distortion of the planar cyclo­trisiloxane ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021672/lh2096sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021672/lh2096Isup2.hkl
Contains datablock I

CCDC reference: 613774

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.117
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT318_ALERT_2_C Check Hybridisation of N1 in Main Residue . ? PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,1-Bis(tert-butylamido)-3,3,5,5-tetraphenylcyclotrisiloxane top
Crystal data top
C32H40N2O3Si3F(000) = 1248
Mr = 584.93Dx = 1.199 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 10563 reflections
a = 10.246 (2) Åθ = 3.4–27.5°
b = 15.759 (3) ŵ = 0.18 mm1
c = 20.087 (4) ÅT = 173 K
β = 92.94 (3)°Block, colourless
V = 3239.1 (11) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
5714 independent reflections
Radiation source: fine-focus sealed tube4160 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 1212
Tmin = 0.965, Tmax = 0.982k = 1818
10563 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0481P)2 + 1.5999P]
where P = (Fo2 + 2Fc2)/3
5714 reflections(Δ/σ)max = 0.001
367 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (300 MHz, 298 K, toluene-d8, δ, p.p.m.): 7.87, 7.18 (m, 20H, C6H5), 2.12 (s, 2H, NH), 1.17 [s, 18H, C(CH3)3]; 13C NMR (300 MHz, 298 K, THF-d8, δ, p.p.m.): 136.1–125.3 (C6H5), 54.4 [C(CH3)3], 38.9, [C(CH3)3]; 29Si NMR (300 MHz, 298 K, toluene-d8, δ, p.p.m.): -34.6, -66.6 [s, SiPh2, Si(NH-tBu)2].

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
xyzUiso*/Ueq
Si10.44061 (6)0.84847 (4)0.15038 (3)0.02615 (17)
Si20.47114 (6)0.76505 (4)0.28321 (3)0.02708 (17)
Si30.53534 (6)0.66909 (4)0.16101 (3)0.02892 (18)
O10.42577 (15)0.84029 (9)0.23087 (8)0.0280 (4)
O20.54861 (15)0.69361 (9)0.24102 (8)0.0300 (4)
O30.49510 (15)0.75807 (9)0.12311 (8)0.0294 (4)
N10.6785 (2)0.62967 (12)0.13621 (11)0.0380 (5)
H1A0.68100.57410.13250.057*
N20.4094 (2)0.60219 (12)0.14210 (11)0.0359 (5)
H2A0.35060.62400.11360.054*
C10.5603 (2)0.93426 (13)0.13678 (12)0.0271 (5)
C20.6207 (2)0.97887 (15)0.18976 (13)0.0367 (6)
H20.59760.96650.23390.044*
C30.7142 (3)1.04120 (16)0.17945 (15)0.0438 (7)
H30.75421.07090.21620.053*
C40.7480 (2)1.05932 (16)0.11562 (15)0.0410 (7)
H40.81201.10150.10840.049*
C50.6894 (3)1.01666 (15)0.06199 (14)0.0406 (7)
H50.71291.02940.01800.049*
C60.5959 (2)0.95501 (14)0.07267 (13)0.0338 (6)
H60.55530.92630.03550.041*
C70.2784 (2)0.86649 (14)0.10742 (12)0.0289 (5)
C80.1984 (3)0.93300 (17)0.12560 (13)0.0416 (7)
H80.22780.97080.16000.050*
C90.0753 (3)0.94488 (19)0.09385 (15)0.0502 (8)
H90.02120.99020.10700.060*
C100.0322 (3)0.89113 (18)0.04362 (14)0.0446 (7)
H100.05150.89940.02210.054*
C110.1095 (3)0.82565 (17)0.02454 (14)0.0421 (7)
H110.07970.78870.01040.051*
C120.2313 (2)0.81332 (16)0.05631 (13)0.0367 (6)
H120.28400.76740.04290.044*
C130.3209 (2)0.72330 (14)0.31896 (12)0.0286 (5)
C140.3263 (3)0.67692 (18)0.37800 (14)0.0451 (7)
H140.40890.66680.40030.054*
C150.2151 (3)0.64516 (19)0.40504 (15)0.0523 (8)
H150.22180.61430.44570.063*
C160.0950 (3)0.65812 (18)0.37333 (15)0.0468 (7)
H160.01840.63600.39160.056*
C170.0868 (3)0.7034 (2)0.31485 (15)0.0504 (8)
H170.00390.71250.29260.061*
C180.1980 (3)0.73581 (18)0.28808 (14)0.0435 (7)
H180.19010.76730.24770.052*
C190.5854 (2)0.80766 (14)0.34997 (12)0.0301 (5)
C200.5397 (3)0.86022 (16)0.39989 (13)0.0402 (6)
H200.44900.87250.40030.048*
C210.6244 (3)0.89467 (17)0.44877 (14)0.0475 (7)
H210.59160.93050.48210.057*
C220.7557 (3)0.87696 (18)0.44898 (15)0.0487 (7)
H220.81370.90090.48230.058*
C230.8032 (3)0.82485 (18)0.40135 (15)0.0480 (7)
H230.89390.81220.40200.058*
C240.7190 (2)0.79058 (17)0.35220 (13)0.0396 (6)
H240.75320.75470.31930.047*
C250.7997 (2)0.67347 (16)0.11981 (13)0.0373 (6)
C260.9158 (3)0.6156 (2)0.1352 (2)0.0743 (11)
H26A0.92000.60110.18270.111*
H26B0.99640.64480.12420.111*
H26C0.90600.56370.10860.111*
C270.7891 (4)0.6963 (3)0.04581 (16)0.0823 (12)
H27A0.77520.64460.01930.123*
H27B0.87000.72400.03340.123*
H27C0.71530.73500.03720.123*
C280.8178 (3)0.75422 (16)0.16022 (15)0.0461 (7)
H28A0.74680.79390.14810.069*
H28B0.90180.78030.15090.069*
H28C0.81650.74080.20780.069*
C290.3770 (2)0.51545 (15)0.16310 (14)0.0369 (6)
C300.4793 (3)0.48447 (18)0.21524 (16)0.0525 (8)
H30A0.56520.48340.19590.079*
H30B0.45650.42720.22970.079*
H30C0.48190.52290.25360.079*
C310.3725 (4)0.45626 (18)0.10318 (16)0.0609 (9)
H31A0.30240.47420.07120.091*
H31B0.35560.39820.11790.091*
H31C0.45630.45830.08190.091*
C320.2430 (3)0.51695 (19)0.19301 (17)0.0577 (9)
H32A0.24470.55640.23070.087*
H32B0.22130.45990.20840.087*
H32C0.17700.53550.15910.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0272 (4)0.0257 (3)0.0258 (4)0.0003 (3)0.0034 (3)0.0016 (3)
Si20.0254 (4)0.0282 (3)0.0278 (4)0.0010 (3)0.0029 (3)0.0036 (3)
Si30.0277 (4)0.0253 (3)0.0343 (4)0.0004 (3)0.0074 (3)0.0006 (3)
O10.0330 (9)0.0268 (8)0.0248 (9)0.0047 (7)0.0053 (7)0.0032 (7)
O20.0276 (9)0.0286 (8)0.0341 (10)0.0041 (7)0.0028 (7)0.0019 (7)
O30.0332 (9)0.0260 (8)0.0295 (9)0.0010 (7)0.0059 (7)0.0005 (7)
N10.0371 (13)0.0268 (10)0.0514 (14)0.0035 (9)0.0168 (11)0.0006 (10)
N20.0354 (12)0.0309 (11)0.0410 (13)0.0040 (9)0.0014 (10)0.0070 (9)
C10.0272 (13)0.0241 (11)0.0301 (13)0.0058 (9)0.0028 (10)0.0023 (10)
C20.0400 (16)0.0373 (14)0.0322 (15)0.0039 (11)0.0038 (12)0.0036 (11)
C30.0394 (16)0.0399 (15)0.0507 (18)0.0077 (12)0.0108 (13)0.0016 (13)
C40.0282 (14)0.0333 (13)0.062 (2)0.0037 (11)0.0058 (13)0.0031 (13)
C50.0422 (16)0.0347 (14)0.0466 (17)0.0016 (12)0.0183 (13)0.0048 (12)
C60.0395 (15)0.0299 (13)0.0325 (15)0.0010 (11)0.0060 (12)0.0025 (11)
C70.0278 (13)0.0310 (12)0.0282 (14)0.0026 (10)0.0049 (10)0.0053 (10)
C80.0404 (16)0.0505 (16)0.0333 (15)0.0090 (12)0.0023 (12)0.0047 (12)
C90.0388 (17)0.0641 (19)0.0479 (18)0.0195 (14)0.0034 (14)0.0007 (15)
C100.0331 (15)0.0559 (17)0.0442 (17)0.0046 (13)0.0054 (13)0.0083 (14)
C110.0406 (16)0.0412 (15)0.0436 (17)0.0121 (12)0.0072 (13)0.0040 (13)
C120.0363 (15)0.0324 (13)0.0411 (16)0.0045 (11)0.0017 (12)0.0028 (11)
C130.0271 (13)0.0299 (12)0.0289 (13)0.0015 (10)0.0036 (10)0.0015 (10)
C140.0333 (15)0.0595 (17)0.0419 (17)0.0089 (13)0.0031 (12)0.0189 (14)
C150.0449 (18)0.0647 (19)0.0476 (18)0.0138 (14)0.0064 (14)0.0192 (15)
C160.0376 (16)0.0528 (17)0.0512 (18)0.0140 (13)0.0149 (14)0.0025 (14)
C170.0275 (15)0.073 (2)0.0507 (19)0.0048 (14)0.0005 (13)0.0012 (16)
C180.0345 (15)0.0592 (17)0.0370 (16)0.0029 (13)0.0028 (12)0.0083 (13)
C190.0327 (14)0.0284 (12)0.0295 (14)0.0019 (10)0.0031 (11)0.0062 (10)
C200.0411 (16)0.0391 (14)0.0404 (16)0.0054 (12)0.0022 (13)0.0017 (12)
C210.065 (2)0.0408 (15)0.0367 (16)0.0040 (14)0.0026 (14)0.0085 (13)
C220.054 (2)0.0464 (16)0.0442 (18)0.0136 (14)0.0075 (14)0.0013 (14)
C230.0363 (16)0.0600 (18)0.0474 (18)0.0078 (13)0.0006 (13)0.0041 (15)
C240.0319 (15)0.0477 (16)0.0394 (16)0.0029 (12)0.0035 (12)0.0041 (12)
C250.0281 (14)0.0451 (15)0.0396 (15)0.0015 (11)0.0108 (11)0.0038 (12)
C260.0378 (18)0.058 (2)0.128 (3)0.0112 (15)0.013 (2)0.014 (2)
C270.083 (3)0.124 (3)0.041 (2)0.053 (2)0.0147 (18)0.002 (2)
C280.0361 (15)0.0423 (15)0.0604 (19)0.0039 (12)0.0073 (14)0.0034 (14)
C290.0352 (15)0.0283 (13)0.0468 (16)0.0032 (11)0.0003 (12)0.0030 (12)
C300.0494 (18)0.0463 (16)0.061 (2)0.0084 (13)0.0099 (15)0.0204 (15)
C310.081 (2)0.0387 (16)0.062 (2)0.0022 (15)0.0047 (18)0.0060 (15)
C320.0445 (18)0.0525 (18)0.077 (2)0.0071 (14)0.0125 (16)0.0155 (16)
Geometric parameters (Å, º) top
Si1—O31.6349 (16)C15—C161.372 (4)
Si1—O11.6366 (17)C15—H150.9500
Si1—C71.855 (2)C16—C171.373 (4)
Si1—C11.855 (2)C16—H160.9500
Si2—O11.6363 (16)C17—C181.382 (4)
Si2—O21.6386 (16)C17—H170.9500
Si2—C131.852 (2)C18—H180.9500
Si2—C191.860 (3)C19—C241.394 (3)
Si3—O31.6382 (16)C19—C201.400 (3)
Si3—O21.6518 (18)C20—C211.387 (4)
Si3—N11.691 (2)C20—H200.9500
Si3—N21.694 (2)C21—C221.374 (4)
N1—C251.473 (3)C21—H210.9500
N1—H1A0.8800C22—C231.369 (4)
N2—C291.473 (3)C22—H220.9500
N2—H2A0.8800C23—C241.386 (4)
C1—C21.393 (3)C23—H230.9500
C1—C61.395 (3)C24—H240.9500
C2—C31.395 (3)C25—C281.516 (4)
C2—H20.9500C25—C261.518 (4)
C3—C41.375 (4)C25—C271.528 (4)
C3—H30.9500C26—H26A0.9800
C4—C51.381 (4)C26—H26B0.9800
C4—H40.9500C26—H26C0.9800
C5—C61.389 (3)C27—H27A0.9800
C5—H50.9500C27—H27B0.9800
C6—H60.9500C27—H27C0.9800
C7—C81.391 (3)C28—H28A0.9800
C7—C121.392 (3)C28—H28B0.9800
C8—C91.396 (4)C28—H28C0.9800
C8—H80.9500C29—C311.522 (4)
C9—C101.373 (4)C29—C301.523 (4)
C9—H90.9500C29—C321.527 (4)
C10—C111.367 (4)C30—H30A0.9800
C10—H100.9500C30—H30B0.9800
C11—C121.386 (4)C30—H30C0.9800
C11—H110.9500C31—H31A0.9800
C12—H120.9500C31—H31B0.9800
C13—C181.389 (4)C31—H31C0.9800
C13—C141.392 (3)C32—H32A0.9800
C14—C151.381 (4)C32—H32B0.9800
C14—H140.9500C32—H32C0.9800
O3—Si1—O1108.24 (8)C17—C16—H16120.4
O3—Si1—C7106.90 (10)C16—C17—C18120.6 (3)
O1—Si1—C7110.19 (10)C16—C17—H17119.7
O3—Si1—C1110.24 (10)C18—C17—H17119.7
O1—Si1—C1107.37 (10)C17—C18—C13121.3 (3)
C7—Si1—C1113.79 (10)C17—C18—H18119.3
O1—Si2—O2107.15 (9)C13—C18—H18119.3
O1—Si2—C13106.99 (10)C24—C19—C20117.1 (2)
O2—Si2—C13113.00 (9)C24—C19—Si2122.31 (19)
O1—Si2—C19110.44 (10)C20—C19—Si2120.56 (19)
O2—Si2—C19108.49 (10)C21—C20—C19121.2 (3)
C13—Si2—C19110.71 (11)C21—C20—H20119.4
O3—Si3—O2104.96 (8)C19—C20—H20119.4
O3—Si3—N1112.27 (10)C22—C21—C20120.0 (3)
O2—Si3—N1110.07 (10)C22—C21—H21120.0
O3—Si3—N2104.95 (10)C20—C21—H21120.0
O2—Si3—N2112.79 (10)C23—C22—C21120.2 (3)
N1—Si3—N2111.56 (11)C23—C22—H22119.9
Si2—O1—Si1130.85 (10)C21—C22—H22119.9
Si2—O2—Si3130.24 (10)C22—C23—C24120.1 (3)
Si1—O3—Si3132.25 (11)C22—C23—H23120.0
C25—N1—Si3130.37 (17)C24—C23—H23120.0
C25—N1—H1A114.8C23—C24—C19121.4 (3)
Si3—N1—H1A114.8C23—C24—H24119.3
C29—N2—Si3133.88 (17)C19—C24—H24119.3
C29—N2—H2A113.1N1—C25—C28110.8 (2)
Si3—N2—H2A113.1N1—C25—C26109.5 (2)
C2—C1—C6117.4 (2)C28—C25—C26108.8 (2)
C2—C1—Si1121.75 (18)N1—C25—C27108.0 (2)
C6—C1—Si1120.85 (18)C28—C25—C27108.9 (3)
C1—C2—C3121.5 (2)C26—C25—C27110.8 (3)
C1—C2—H2119.2C25—C26—H26A109.5
C3—C2—H2119.2C25—C26—H26B109.5
C4—C3—C2119.5 (3)H26A—C26—H26B109.5
C4—C3—H3120.2C25—C26—H26C109.5
C2—C3—H3120.2H26A—C26—H26C109.5
C3—C4—C5120.4 (2)H26B—C26—H26C109.5
C3—C4—H4119.8C25—C27—H27A109.5
C5—C4—H4119.8C25—C27—H27B109.5
C4—C5—C6119.7 (2)H27A—C27—H27B109.5
C4—C5—H5120.1C25—C27—H27C109.5
C6—C5—H5120.1H27A—C27—H27C109.5
C5—C6—C1121.4 (2)H27B—C27—H27C109.5
C5—C6—H6119.3C25—C28—H28A109.5
C1—C6—H6119.3C25—C28—H28B109.5
C8—C7—C12117.4 (2)H28A—C28—H28B109.5
C8—C7—Si1121.30 (19)C25—C28—H28C109.5
C12—C7—Si1121.29 (19)H28A—C28—H28C109.5
C7—C8—C9120.8 (3)H28B—C28—H28C109.5
C7—C8—H8119.6N2—C29—C31109.9 (2)
C9—C8—H8119.6N2—C29—C30109.7 (2)
C10—C9—C8120.1 (3)C31—C29—C30109.8 (2)
C10—C9—H9119.9N2—C29—C32108.6 (2)
C8—C9—H9119.9C31—C29—C32109.2 (2)
C11—C10—C9120.2 (3)C30—C29—C32109.6 (2)
C11—C10—H10119.9C29—C30—H30A109.5
C9—C10—H10119.9C29—C30—H30B109.5
C10—C11—C12119.8 (3)H30A—C30—H30B109.5
C10—C11—H11120.1C29—C30—H30C109.5
C12—C11—H11120.1H30A—C30—H30C109.5
C11—C12—C7121.7 (2)H30B—C30—H30C109.5
C11—C12—H12119.2C29—C31—H31A109.5
C7—C12—H12119.2C29—C31—H31B109.5
C18—C13—C14116.8 (2)H31A—C31—H31B109.5
C18—C13—Si2121.93 (19)C29—C31—H31C109.5
C14—C13—Si2121.29 (19)H31A—C31—H31C109.5
C15—C14—C13121.9 (3)H31B—C31—H31C109.5
C15—C14—H14119.1C29—C32—H32A109.5
C13—C14—H14119.1C29—C32—H32B109.5
C16—C15—C14120.1 (3)H32A—C32—H32B109.5
C16—C15—H15119.9C29—C32—H32C109.5
C14—C15—H15119.9H32A—C32—H32C109.5
C15—C16—C17119.3 (3)H32B—C32—H32C109.5
C15—C16—H16120.4
 

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