Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028028/br6168sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028028/br6168Isup2.hkl |
CCDC reference: 259117
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.061
- wR factor = 0.178
- Data-to-parameter ratio = 23.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for Si2 - C10 .. 5.29 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 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
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C13H34O6P2Si2 | Z = 2 |
Mr = 404.52 | F(000) = 436 |
Triclinic, P1 | Dx = 1.236 Mg m−3 |
Hall symbol: -P 1 | Melting point: 313(1) K |
a = 6.534 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.130 (2) Å | Cell parameters from 3959 reflections |
c = 16.325 (2) Å | θ = 1.8–29.4° |
α = 100.64 (1)° | µ = 0.33 mm−1 |
β = 100.25 (1)° | T = 100 K |
γ = 106.23 (2)° | Prism, colorless |
V = 1086.6 (4) Å3 | 0.37 × 0.13 × 0.02 mm |
Oxford Diffraction Xcalibur3 diffractometer equipped with a CCD detector | 4971 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3556 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 27.5°, θmin = 4.2° |
Absorption correction: numerical (Clark & Reid, 1995) | h = −8→7 |
Tmin = 0.888, Tmax = 0.983 | k = −14→14 |
10850 measured reflections | l = −21→21 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
4971 reflections | (Δ/σ)max < 0.001 |
214 parameters | Δρmax = 1.00 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
Experimental. Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R·C. Clark & J·S. Reid. (Clark & Reid, 1995) |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7308 (4) | 0.9586 (3) | 0.07610 (19) | 0.0266 (7) | |
H1A | 0.7430 | 1.0399 | 0.0606 | 0.032* | |
H1B | 0.7628 | 0.9020 | 0.0309 | 0.032* | |
C2 | 0.8949 (5) | 0.9821 (3) | 0.15949 (18) | 0.0245 (6) | |
H2A | 0.9009 | 0.8998 | 0.1696 | 0.029* | |
H2B | 0.8467 | 1.0247 | 0.2062 | 0.029* | |
C3 | 1.1261 (5) | 1.0657 (3) | 0.15930 (18) | 0.0236 (6) | |
H3A | 1.1167 | 1.1447 | 0.1443 | 0.028* | |
H3B | 1.1776 | 1.0197 | 0.1152 | 0.028* | |
C4 | 1.2286 (5) | 1.1882 (4) | 0.3517 (2) | 0.0333 (7) | |
H4A | 1.0940 | 1.1293 | 0.3557 | 0.050* | |
H4B | 1.2025 | 1.2642 | 0.3389 | 0.050* | |
H4C | 1.3359 | 1.2118 | 0.4053 | 0.050* | |
C5 | 1.3742 (5) | 0.9597 (3) | 0.2894 (2) | 0.0306 (7) | |
H5A | 1.4199 | 0.9152 | 0.2435 | 0.046* | |
H5B | 1.2389 | 0.9045 | 0.2957 | 0.046* | |
H5C | 1.4852 | 0.9824 | 0.3419 | 0.046* | |
C6 | 1.5974 (5) | 1.2221 (3) | 0.2584 (2) | 0.0290 (7) | |
H6A | 1.7099 | 1.2322 | 0.3082 | 0.043* | |
H6B | 1.5806 | 1.3046 | 0.2563 | 0.043* | |
H6C | 1.6381 | 1.1879 | 0.2076 | 0.043* | |
C7 | 0.0968 (5) | 0.4456 (3) | 0.21447 (19) | 0.0249 (6) | |
H7A | 0.1727 | 0.3831 | 0.2207 | 0.030* | |
H7B | −0.0511 | 0.4000 | 0.1794 | 0.030* | |
C8 | 0.0894 (5) | 0.5167 (3) | 0.30150 (18) | 0.0232 (6) | |
H8A | 0.2387 | 0.5619 | 0.3353 | 0.028* | |
H8B | 0.0203 | 0.4542 | 0.3308 | 0.028* | |
C9 | −0.0351 (5) | 0.6139 (3) | 0.29746 (18) | 0.0233 (6) | |
H9A | −0.1772 | 0.5707 | 0.2572 | 0.028* | |
H9B | 0.0452 | 0.6821 | 0.2747 | 0.028* | |
C10 | 0.1891 (6) | 0.7757 (4) | 0.4815 (2) | 0.0385 (8) | |
H10A | 0.2669 | 0.7157 | 0.4901 | 0.058* | |
H10B | 0.1637 | 0.8130 | 0.5351 | 0.058* | |
H10C | 0.2751 | 0.8427 | 0.4603 | 0.058* | |
C11 | −0.2517 (5) | 0.5594 (3) | 0.4417 (2) | 0.0327 (7) | |
H11A | −0.3837 | 0.5110 | 0.3981 | 0.049* | |
H11B | −0.2889 | 0.5977 | 0.4923 | 0.049* | |
H11C | −0.1708 | 0.5029 | 0.4555 | 0.049* | |
C12 | −0.2285 (6) | 0.8063 (4) | 0.3837 (2) | 0.0378 (8) | |
H12A | −0.1419 | 0.8721 | 0.3618 | 0.057* | |
H12B | −0.2530 | 0.8452 | 0.4370 | 0.057* | |
H12C | −0.3672 | 0.7618 | 0.3429 | 0.057* | |
C13 | 0.5061 (5) | 0.6658 (3) | 0.10563 (18) | 0.0217 (6) | |
H13A | 0.6340 | 0.6576 | 0.0856 | 0.026* | |
H13B | 0.5577 | 0.7169 | 0.1647 | 0.026* | |
O1 | 0.3779 (3) | 0.7121 (2) | −0.04950 (12) | 0.0251 (5) | |
O2 | 0.1511 (3) | 0.7452 (2) | 0.05977 (13) | 0.0249 (5) | |
H2 | 0.0683 | 0.6704 | 0.0423 | 0.037* | |
O3 | 0.5065 (3) | 0.89973 (19) | 0.08340 (13) | 0.0228 (4) | |
O4 | 0.1958 (3) | 0.4386 (2) | 0.01683 (13) | 0.0244 (5) | |
O5 | 0.4835 (3) | 0.4356 (2) | 0.14237 (12) | 0.0246 (5) | |
H5 | 0.5660 | 0.4247 | 0.1113 | 0.037* | |
O6 | 0.2130 (3) | 0.5408 (2) | 0.17442 (13) | 0.0277 (5) | |
P1 | 0.37690 (11) | 0.75255 (7) | 0.04168 (5) | 0.0198 (2) | |
P2 | 0.33550 (12) | 0.50793 (7) | 0.10407 (5) | 0.0200 (2) | |
Si1 | 1.33252 (13) | 1.10894 (8) | 0.26433 (5) | 0.0212 (2) | |
Si2 | −0.08000 (13) | 0.68904 (8) | 0.40161 (5) | 0.0236 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0178 (15) | 0.0302 (17) | 0.0289 (16) | 0.0015 (13) | 0.0037 (12) | 0.0123 (13) |
C2 | 0.0235 (15) | 0.0252 (16) | 0.0216 (14) | 0.0052 (12) | 0.0027 (11) | 0.0044 (12) |
C3 | 0.0243 (15) | 0.0240 (15) | 0.0247 (14) | 0.0090 (12) | 0.0075 (12) | 0.0078 (12) |
C4 | 0.0358 (18) | 0.043 (2) | 0.0252 (16) | 0.0194 (16) | 0.0097 (14) | 0.0057 (15) |
C5 | 0.0346 (18) | 0.0248 (17) | 0.0325 (17) | 0.0086 (14) | 0.0051 (14) | 0.0117 (14) |
C6 | 0.0266 (16) | 0.0293 (17) | 0.0299 (16) | 0.0074 (13) | 0.0025 (13) | 0.0116 (14) |
C7 | 0.0310 (16) | 0.0208 (15) | 0.0257 (15) | 0.0072 (13) | 0.0119 (12) | 0.0095 (12) |
C8 | 0.0266 (15) | 0.0233 (15) | 0.0221 (14) | 0.0089 (12) | 0.0071 (12) | 0.0092 (12) |
C9 | 0.0275 (15) | 0.0213 (15) | 0.0209 (14) | 0.0082 (12) | 0.0047 (11) | 0.0052 (12) |
C10 | 0.047 (2) | 0.036 (2) | 0.0280 (17) | 0.0114 (17) | 0.0048 (15) | 0.0051 (15) |
C11 | 0.0334 (18) | 0.0332 (18) | 0.0359 (18) | 0.0126 (15) | 0.0164 (14) | 0.0091 (15) |
C12 | 0.047 (2) | 0.036 (2) | 0.0412 (19) | 0.0241 (17) | 0.0195 (16) | 0.0119 (16) |
C13 | 0.0199 (14) | 0.0232 (15) | 0.0213 (14) | 0.0075 (12) | 0.0038 (11) | 0.0044 (12) |
O1 | 0.0296 (11) | 0.0285 (12) | 0.0210 (10) | 0.0155 (9) | 0.0052 (8) | 0.0071 (9) |
O2 | 0.0177 (10) | 0.0238 (11) | 0.0323 (11) | 0.0070 (9) | 0.0082 (8) | 0.0026 (9) |
O3 | 0.0174 (10) | 0.0204 (11) | 0.0280 (11) | 0.0059 (8) | 0.0021 (8) | 0.0029 (9) |
O4 | 0.0193 (10) | 0.0255 (11) | 0.0270 (11) | 0.0076 (9) | 0.0040 (8) | 0.0041 (9) |
O5 | 0.0298 (11) | 0.0274 (12) | 0.0214 (10) | 0.0163 (9) | 0.0056 (8) | 0.0073 (9) |
O6 | 0.0383 (13) | 0.0240 (11) | 0.0311 (12) | 0.0154 (10) | 0.0206 (10) | 0.0116 (9) |
P1 | 0.0187 (4) | 0.0202 (4) | 0.0208 (4) | 0.0085 (3) | 0.0034 (3) | 0.0041 (3) |
P2 | 0.0217 (4) | 0.0206 (4) | 0.0212 (4) | 0.0108 (3) | 0.0065 (3) | 0.0063 (3) |
Si1 | 0.0209 (4) | 0.0210 (4) | 0.0219 (4) | 0.0073 (3) | 0.0037 (3) | 0.0065 (3) |
Si2 | 0.0264 (5) | 0.0247 (5) | 0.0220 (4) | 0.0109 (4) | 0.0072 (3) | 0.0061 (3) |
C1—O3 | 1.464 (3) | C8—H8B | 0.9700 |
C1—C2 | 1.505 (4) | C9—Si2 | 1.861 (3) |
C1—H1A | 0.9700 | C9—H9A | 0.9700 |
C1—H1B | 0.9700 | C9—H9B | 0.9700 |
C2—C3 | 1.538 (4) | C10—Si2 | 1.869 (4) |
C2—H2A | 0.9700 | C10—H10A | 0.9600 |
C2—H2B | 0.9700 | C10—H10B | 0.9600 |
C3—Si1 | 1.871 (3) | C10—H10C | 0.9600 |
C3—H3A | 0.9700 | C11—Si2 | 1.864 (3) |
C3—H3B | 0.9700 | C11—H11A | 0.9600 |
C4—Si1 | 1.867 (3) | C11—H11B | 0.9600 |
C4—H4A | 0.9600 | C11—H11C | 0.9600 |
C4—H4B | 0.9600 | C12—Si2 | 1.865 (3) |
C4—H4C | 0.9600 | C12—H12A | 0.9600 |
C5—Si1 | 1.862 (3) | C12—H12B | 0.9600 |
C5—H5A | 0.9600 | C12—H12C | 0.9600 |
C5—H5B | 0.9600 | C13—P2 | 1.791 (3) |
C5—H5C | 0.9600 | C13—P1 | 1.803 (3) |
C6—Si1 | 1.865 (3) | C13—H13A | 0.9700 |
C6—H6A | 0.9600 | C13—H13B | 0.9700 |
C6—H6B | 0.9600 | O1—P1 | 1.475 (2) |
C6—H6C | 0.9600 | O2—P1 | 1.539 (2) |
C7—O6 | 1.453 (3) | O2—H2 | 0.8200 |
C7—C8 | 1.509 (4) | O3—P1 | 1.572 (2) |
C7—H7A | 0.9700 | O4—P2 | 1.481 (2) |
C7—H7B | 0.9700 | O5—P2 | 1.543 (2) |
C8—C9 | 1.529 (4) | O5—H5 | 0.8200 |
C8—H8A | 0.9700 | O6—P2 | 1.559 (2) |
O3—C1—C2 | 110.9 (2) | H9A—C9—H9B | 107.5 |
O3—C1—H1A | 109.5 | Si2—C10—H10A | 109.5 |
C2—C1—H1A | 109.5 | Si2—C10—H10B | 109.5 |
O3—C1—H1B | 109.5 | H10A—C10—H10B | 109.5 |
C2—C1—H1B | 109.5 | Si2—C10—H10C | 109.5 |
H1A—C1—H1B | 108.1 | H10A—C10—H10C | 109.5 |
C1—C2—C3 | 112.1 (2) | H10B—C10—H10C | 109.5 |
C1—C2—H2A | 109.2 | Si2—C11—H11A | 109.5 |
C3—C2—H2A | 109.2 | Si2—C11—H11B | 109.5 |
C1—C2—H2B | 109.2 | H11A—C11—H11B | 109.5 |
C3—C2—H2B | 109.2 | Si2—C11—H11C | 109.5 |
H2A—C2—H2B | 107.9 | H11A—C11—H11C | 109.5 |
C2—C3—Si1 | 114.02 (19) | H11B—C11—H11C | 109.5 |
C2—C3—H3A | 108.7 | Si2—C12—H12A | 109.5 |
Si1—C3—H3A | 108.7 | Si2—C12—H12B | 109.5 |
C2—C3—H3B | 108.7 | H12A—C12—H12B | 109.5 |
Si1—C3—H3B | 108.7 | Si2—C12—H12C | 109.5 |
H3A—C3—H3B | 107.6 | H12A—C12—H12C | 109.5 |
Si1—C4—H4A | 109.5 | H12B—C12—H12C | 109.5 |
Si1—C4—H4B | 109.5 | P2—C13—P1 | 115.45 (15) |
H4A—C4—H4B | 109.5 | P2—C13—H13A | 108.4 |
Si1—C4—H4C | 109.5 | P1—C13—H13A | 108.4 |
H4A—C4—H4C | 109.5 | P2—C13—H13B | 108.4 |
H4B—C4—H4C | 109.5 | P1—C13—H13B | 108.4 |
Si1—C5—H5A | 109.5 | H13A—C13—H13B | 107.5 |
Si1—C5—H5B | 109.5 | P1—O2—H2 | 109.5 |
H5A—C5—H5B | 109.5 | C1—O3—P1 | 121.46 (19) |
Si1—C5—H5C | 109.5 | P2—O5—H5 | 109.5 |
H5A—C5—H5C | 109.5 | C7—O6—P2 | 123.21 (18) |
H5B—C5—H5C | 109.5 | O1—P1—O2 | 115.79 (12) |
Si1—C6—H6A | 109.5 | O1—P1—O3 | 113.16 (12) |
Si1—C6—H6B | 109.5 | O2—P1—O3 | 100.31 (11) |
H6A—C6—H6B | 109.5 | O1—P1—C13 | 111.17 (13) |
Si1—C6—H6C | 109.5 | O2—P1—C13 | 109.79 (12) |
H6A—C6—H6C | 109.5 | O3—P1—C13 | 105.72 (12) |
H6B—C6—H6C | 109.5 | O4—P2—O5 | 113.86 (12) |
O6—C7—C8 | 107.5 (2) | O4—P2—O6 | 116.29 (12) |
O6—C7—H7A | 110.2 | O5—P2—O6 | 104.70 (11) |
C8—C7—H7A | 110.2 | O4—P2—C13 | 111.41 (12) |
O6—C7—H7B | 110.2 | O5—P2—C13 | 108.38 (13) |
C8—C7—H7B | 110.2 | O6—P2—C13 | 101.16 (13) |
H7A—C7—H7B | 108.5 | C5—Si1—C6 | 110.22 (15) |
C7—C8—C9 | 113.7 (2) | C5—Si1—C4 | 108.40 (15) |
C7—C8—H8A | 108.8 | C6—Si1—C4 | 109.39 (16) |
C9—C8—H8A | 108.8 | C5—Si1—C3 | 109.60 (14) |
C7—C8—H8B | 108.8 | C6—Si1—C3 | 109.63 (13) |
C9—C8—H8B | 108.8 | C4—Si1—C3 | 109.59 (14) |
H8A—C8—H8B | 107.7 | C9—Si2—C11 | 108.58 (15) |
C8—C9—Si2 | 115.46 (19) | C9—Si2—C12 | 108.90 (14) |
C8—C9—H9A | 108.4 | C11—Si2—C12 | 109.31 (16) |
Si2—C9—H9A | 108.4 | C9—Si2—C10 | 110.31 (15) |
C8—C9—H9B | 108.4 | C11—Si2—C10 | 110.35 (16) |
Si2—C9—H9B | 108.4 | C12—Si2—C10 | 109.37 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4i | 0.82 | 1.78 | 2.518 (3) | 148 |
O5—H5···O1ii | 0.82 | 1.83 | 2.493 (3) | 137 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z. |