Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701361X/kp2079sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680701361X/kp2079Isup2.hkl |
CCDC reference: 647256
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.066
- wR factor = 0.152
- Data-to-parameter ratio = 26.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.81 Ratio
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.00 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Si2 PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. O5 .. 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15C .. O5 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H18C .. O13 .. 2.62 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 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 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SCAIL (McArdle, 1995), PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).
C16H26N2O4Si2 | F(000) = 784 |
Mr = 366.57 | Dx = 1.239 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8711 reflections |
a = 12.5402 (12) Å | θ = 2.7–30.5° |
b = 8.1958 (8) Å | µ = 0.20 mm−1 |
c = 19.3421 (19) Å | T = 100 K |
β = 98.786 (2)° | Block, colourless |
V = 1964.6 (3) Å3 | 0.53 × 0.41 × 0.18 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 5968 independent reflections |
Radiation source: fine-focus sealed tube | 5726 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 30.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003) | h = −17→17 |
Tmin = 0.933, Tmax = 0.968 | k = −11→11 |
22233 measured reflections | l = −27→27 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.22 | w = 1/[σ2(Fo2) + (0.0424P)2 + 2.5797P] where P = (Fo2 + 2Fc2)/3 |
5968 reflections | (Δ/σ)max < 0.001 |
225 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
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) 3.796 (12) x - 4.176 (7) y + 14.503 (12) z = 3.236 (11) #O(1) -0.001 (2) #N(2) 0.003 (2) #N(3) -0.004 (2) #C(4) 0.003 (2) #C(5) -0.001 (2) Si(2) 0.015 (1) O(5) -0.021 (2) C(6) -1.100 (3) C(7) -0.585 (4) C(9) 0.039 (2) C(10) -1.096 (2) C(11) -0.878 (2) C(12) 0.340 (2) C(13) 1.426 (2) C(14) 1.288 (2) -2.042 (10) x + 5.026 (5) y + 15.256 (10) z = 10.851 (2) #C(9) 0.000 (2) #C(10) -0.007 (2) #C(11) 0.011 (2) #C(12) -0.008 (2) #C(13) 0.002 (2) #C(14) 0.002 (2) Si(1) 0.022 (1) O(1) 1.015 (2) O(5) -0.699 (2) O(11) 0.064 (2) O(13) 0.054 (2) N(2) 1.237 (2) N(3) 0.067 (2) C(4) -0.931 (2) C(5) -0.330 (2) C(15) 0.116 (3) C(16) 0.124 (2) C(17) -1.186 (2) C(19) -0.562 (2) (Acute) Angles Between Planes 74.88 (10) Degrees |
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 | ||
Si1 | 0.12569 (4) | 1.18677 (7) | 0.33853 (3) | 0.01847 (12) | |
Si2 | 0.41353 (5) | 0.76702 (7) | 0.33679 (3) | 0.02303 (14) | |
O11 | −0.04717 (11) | 0.9864 (2) | 0.38420 (8) | 0.0255 (3) | |
C10 | 0.14125 (15) | 1.0029 (2) | 0.39934 (10) | 0.0182 (3) | |
O1 | 0.46169 (13) | 1.1943 (2) | 0.44611 (8) | 0.0287 (3) | |
N2 | 0.36112 (15) | 1.1530 (2) | 0.46082 (10) | 0.0259 (4) | |
O13 | 0.15069 (14) | 0.6028 (2) | 0.53640 (9) | 0.0312 (4) | |
C11 | 0.04810 (16) | 0.9207 (2) | 0.41508 (10) | 0.0206 (4) | |
N3 | 0.33928 (13) | 1.0156 (2) | 0.42647 (8) | 0.0187 (3) | |
O5 | 0.58695 (13) | 1.0948 (2) | 0.38330 (9) | 0.0348 (4) | |
C4 | 0.41547 (15) | 0.9576 (2) | 0.39034 (10) | 0.0208 (4) | |
C12 | 0.05337 (17) | 0.7860 (3) | 0.45892 (10) | 0.0231 (4) | |
H12 | −0.0109 | 0.7323 | 0.4667 | 0.028* | |
C9 | 0.23740 (15) | 0.9385 (2) | 0.43388 (10) | 0.0185 (3) | |
C14 | 0.24769 (16) | 0.8057 (2) | 0.47910 (10) | 0.0218 (4) | |
H14 | 0.3165 | 0.7683 | 0.5007 | 0.026* | |
C5 | 0.49986 (17) | 1.0760 (3) | 0.40204 (11) | 0.0253 (4) | |
C13 | 0.15353 (18) | 0.7299 (2) | 0.49146 (11) | 0.0237 (4) | |
C16 | −0.14527 (17) | 0.9148 (3) | 0.39858 (12) | 0.0282 (4) | |
H16A | −0.1514 | 0.8034 | 0.3800 | 0.042* | |
H16B | −0.2066 | 0.9798 | 0.3763 | 0.042* | |
H16C | −0.1451 | 0.9122 | 0.4492 | 0.042* | |
C17 | 0.0245 (2) | 1.1438 (3) | 0.26001 (13) | 0.0364 (5) | |
H17A | −0.0474 | 1.1361 | 0.2737 | 0.055* | |
H17B | 0.0423 | 1.0405 | 0.2389 | 0.055* | |
H17C | 0.0253 | 1.2323 | 0.2260 | 0.055* | |
C18 | 0.0907 (3) | 1.3640 (3) | 0.38979 (13) | 0.0412 (6) | |
H18A | 0.0925 | 1.4637 | 0.3620 | 0.062* | |
H18B | 0.1430 | 1.3733 | 0.4328 | 0.062* | |
H18C | 0.0182 | 1.3491 | 0.4018 | 0.062* | |
C19 | 0.25108 (18) | 1.2342 (3) | 0.30142 (13) | 0.0319 (5) | |
H19A | 0.2359 | 1.3202 | 0.2661 | 0.048* | |
H19B | 0.2758 | 1.1359 | 0.2798 | 0.048* | |
H19C | 0.3073 | 1.2715 | 0.3389 | 0.048* | |
C15 | 0.2519 (2) | 0.5467 (3) | 0.57248 (16) | 0.0446 (7) | |
H15A | 0.2951 | 0.5027 | 0.5387 | 0.067* | |
H15B | 0.2396 | 0.4611 | 0.6057 | 0.067* | |
H15C | 0.2905 | 0.6379 | 0.5978 | 0.067* | |
C8 | 0.4510 (3) | 0.5905 (4) | 0.39555 (16) | 0.0557 (9) | |
H8A | 0.4661 | 0.4957 | 0.3677 | 0.084* | |
H8B | 0.3912 | 0.5648 | 0.4210 | 0.084* | |
H8C | 0.5154 | 0.6176 | 0.4290 | 0.084* | |
C7 | 0.5147 (3) | 0.7993 (5) | 0.2782 (2) | 0.0693 (12) | |
H7A | 0.5855 | 0.8188 | 0.3062 | 0.104* | |
H7B | 0.4941 | 0.8940 | 0.2482 | 0.104* | |
H7C | 0.5183 | 0.7022 | 0.2491 | 0.104* | |
C6 | 0.2783 (2) | 0.7327 (4) | 0.28539 (17) | 0.0479 (7) | |
H6A | 0.2557 | 0.8306 | 0.2579 | 0.072* | |
H6B | 0.2265 | 0.7096 | 0.3172 | 0.072* | |
H6C | 0.2813 | 0.6398 | 0.2538 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.0208 (2) | 0.0176 (2) | 0.0166 (2) | −0.00019 (19) | 0.00188 (18) | 0.00105 (18) |
Si2 | 0.0217 (3) | 0.0225 (3) | 0.0253 (3) | −0.0007 (2) | 0.0049 (2) | −0.0012 (2) |
O11 | 0.0184 (6) | 0.0281 (8) | 0.0304 (8) | −0.0012 (6) | 0.0054 (5) | 0.0048 (6) |
C10 | 0.0224 (8) | 0.0166 (8) | 0.0157 (8) | −0.0003 (6) | 0.0036 (6) | −0.0011 (6) |
O1 | 0.0299 (8) | 0.0252 (8) | 0.0289 (8) | −0.0102 (6) | −0.0021 (6) | 0.0006 (6) |
N2 | 0.0308 (9) | 0.0199 (8) | 0.0261 (8) | −0.0060 (7) | 0.0009 (7) | −0.0019 (7) |
O13 | 0.0391 (9) | 0.0243 (8) | 0.0288 (8) | −0.0080 (7) | 0.0005 (6) | 0.0096 (6) |
C11 | 0.0221 (9) | 0.0211 (9) | 0.0189 (8) | −0.0010 (7) | 0.0044 (7) | −0.0019 (7) |
N3 | 0.0214 (7) | 0.0171 (7) | 0.0164 (7) | −0.0022 (6) | −0.0016 (5) | 0.0019 (6) |
O5 | 0.0207 (7) | 0.0429 (10) | 0.0390 (9) | −0.0111 (7) | −0.0008 (6) | 0.0056 (8) |
C4 | 0.0174 (8) | 0.0216 (9) | 0.0225 (9) | −0.0036 (7) | −0.0003 (6) | 0.0028 (7) |
C12 | 0.0274 (9) | 0.0212 (9) | 0.0212 (9) | −0.0051 (7) | 0.0055 (7) | 0.0001 (7) |
C9 | 0.0218 (8) | 0.0161 (8) | 0.0175 (8) | −0.0029 (6) | 0.0026 (6) | −0.0016 (6) |
C14 | 0.0254 (9) | 0.0186 (9) | 0.0204 (8) | −0.0007 (7) | 0.0005 (7) | 0.0018 (7) |
C5 | 0.0239 (9) | 0.0261 (10) | 0.0233 (9) | −0.0057 (8) | −0.0051 (7) | 0.0033 (8) |
C13 | 0.0333 (10) | 0.0166 (9) | 0.0209 (9) | −0.0040 (7) | 0.0033 (7) | 0.0012 (7) |
C16 | 0.0205 (9) | 0.0353 (12) | 0.0298 (10) | −0.0069 (8) | 0.0067 (8) | −0.0044 (9) |
C17 | 0.0333 (12) | 0.0422 (14) | 0.0295 (11) | −0.0099 (10) | −0.0091 (9) | 0.0110 (10) |
C18 | 0.0745 (19) | 0.0239 (11) | 0.0277 (11) | 0.0124 (12) | 0.0154 (12) | 0.0039 (9) |
C19 | 0.0268 (10) | 0.0356 (12) | 0.0333 (11) | −0.0021 (9) | 0.0052 (8) | 0.0163 (10) |
C15 | 0.0497 (15) | 0.0326 (13) | 0.0452 (15) | −0.0107 (11) | −0.0126 (12) | 0.0219 (12) |
C8 | 0.095 (3) | 0.0280 (13) | 0.0397 (15) | 0.0177 (15) | −0.0044 (16) | −0.0040 (11) |
C7 | 0.082 (3) | 0.052 (2) | 0.090 (3) | −0.0268 (18) | 0.064 (2) | −0.0308 (19) |
C6 | 0.0388 (14) | 0.0467 (16) | 0.0523 (17) | 0.0051 (12) | −0.0118 (12) | −0.0252 (14) |
Si1—C18 | 1.849 (3) | C14—H14 | 0.9500 |
Si1—C17 | 1.858 (2) | C16—H16A | 0.9800 |
Si1—C19 | 1.866 (2) | C16—H16B | 0.9800 |
Si1—C10 | 1.903 (2) | C16—H16C | 0.9800 |
Si2—C7 | 1.845 (3) | C17—H17A | 0.9800 |
Si2—C6 | 1.851 (3) | C17—H17B | 0.9800 |
Si2—C8 | 1.856 (3) | C17—H17C | 0.9800 |
Si2—C4 | 1.872 (2) | C18—H18A | 0.9800 |
O11—C11 | 1.362 (2) | C18—H18B | 0.9800 |
O11—C16 | 1.428 (2) | C18—H18C | 0.9800 |
C10—C9 | 1.390 (3) | C19—H19A | 0.9800 |
C10—C11 | 1.421 (3) | C19—H19B | 0.9800 |
O1—N2 | 1.377 (2) | C19—H19C | 0.9800 |
O1—C5 | 1.421 (3) | C15—H15A | 0.9800 |
N2—N3 | 1.315 (2) | C15—H15B | 0.9800 |
O13—C13 | 1.360 (2) | C15—H15C | 0.9800 |
O13—C15 | 1.428 (3) | C8—H8A | 0.9800 |
C11—C12 | 1.388 (3) | C8—H8B | 0.9800 |
N3—C4 | 1.353 (3) | C8—H8C | 0.9800 |
N3—C9 | 1.452 (2) | C7—H7A | 0.9800 |
O5—C5 | 1.212 (3) | C7—H7B | 0.9800 |
C4—C5 | 1.428 (3) | C7—H7C | 0.9800 |
C12—C13 | 1.394 (3) | C6—H6A | 0.9800 |
C12—H12 | 0.9500 | C6—H6B | 0.9800 |
C9—C14 | 1.390 (3) | C6—H6C | 0.9800 |
C14—C13 | 1.387 (3) | ||
C18—Si1—C17 | 113.52 (14) | O11—C16—H16C | 109.5 |
C18—Si1—C19 | 108.98 (14) | H16A—C16—H16C | 109.5 |
C17—Si1—C19 | 103.61 (12) | H16B—C16—H16C | 109.5 |
C18—Si1—C10 | 107.53 (10) | Si1—C17—H17A | 109.5 |
C17—Si1—C10 | 110.36 (10) | Si1—C17—H17B | 109.5 |
C19—Si1—C10 | 112.93 (9) | H17A—C17—H17B | 109.5 |
C7—Si2—C6 | 110.57 (19) | Si1—C17—H17C | 109.5 |
C7—Si2—C8 | 110.8 (2) | H17A—C17—H17C | 109.5 |
C6—Si2—C8 | 109.63 (17) | H17B—C17—H17C | 109.5 |
C7—Si2—C4 | 105.55 (12) | Si1—C18—H18A | 109.5 |
C6—Si2—C4 | 110.93 (11) | Si1—C18—H18B | 109.5 |
C8—Si2—C4 | 109.34 (11) | H18A—C18—H18B | 109.5 |
C11—O11—C16 | 118.43 (17) | Si1—C18—H18C | 109.5 |
C9—C10—C11 | 113.48 (17) | H18A—C18—H18C | 109.5 |
C9—C10—Si1 | 126.65 (14) | H18B—C18—H18C | 109.5 |
C11—C10—Si1 | 119.84 (14) | Si1—C19—H19A | 109.5 |
N2—O1—C5 | 111.06 (15) | Si1—C19—H19B | 109.5 |
N3—N2—O1 | 103.45 (16) | H19A—C19—H19B | 109.5 |
C13—O13—C15 | 116.79 (18) | Si1—C19—H19C | 109.5 |
O11—C11—C12 | 122.63 (18) | H19A—C19—H19C | 109.5 |
O11—C11—C10 | 114.41 (17) | H19B—C19—H19C | 109.5 |
C12—C11—C10 | 122.96 (18) | O13—C15—H15A | 109.5 |
N2—N3—C4 | 116.92 (17) | O13—C15—H15B | 109.5 |
N2—N3—C9 | 116.17 (16) | H15A—C15—H15B | 109.5 |
C4—N3—C9 | 126.85 (16) | O13—C15—H15C | 109.5 |
N3—C4—C5 | 104.13 (18) | H15A—C15—H15C | 109.5 |
N3—C4—Si2 | 128.92 (14) | H15B—C15—H15C | 109.5 |
C5—C4—Si2 | 126.96 (16) | Si2—C8—H8A | 109.5 |
C11—C12—C13 | 119.60 (19) | Si2—C8—H8B | 109.5 |
C11—C12—H12 | 120.2 | H8A—C8—H8B | 109.5 |
C13—C12—H12 | 120.2 | Si2—C8—H8C | 109.5 |
C10—C9—C14 | 126.15 (18) | H8A—C8—H8C | 109.5 |
C10—C9—N3 | 119.96 (17) | H8B—C8—H8C | 109.5 |
C14—C9—N3 | 113.85 (17) | Si2—C7—H7A | 109.5 |
C13—C14—C9 | 117.37 (18) | Si2—C7—H7B | 109.5 |
C13—C14—H14 | 121.3 | H7A—C7—H7B | 109.5 |
C9—C14—H14 | 121.3 | Si2—C7—H7C | 109.5 |
O5—C5—O1 | 119.61 (19) | H7A—C7—H7C | 109.5 |
O5—C5—C4 | 136.0 (2) | H7B—C7—H7C | 109.5 |
O1—C5—C4 | 104.43 (18) | Si2—C6—H6A | 109.5 |
O13—C13—C14 | 124.0 (2) | Si2—C6—H6B | 109.5 |
O13—C13—C12 | 115.55 (19) | H6A—C6—H6B | 109.5 |
C14—C13—C12 | 120.42 (19) | Si2—C6—H6C | 109.5 |
O11—C16—H16A | 109.5 | H6A—C6—H6C | 109.5 |
O11—C16—H16B | 109.5 | H6B—C6—H6C | 109.5 |
H16A—C16—H16B | 109.5 | ||
C18—Si1—C10—C9 | −99.0 (2) | O11—C11—C12—C13 | −176.91 (19) |
C17—Si1—C10—C9 | 136.68 (18) | C10—C11—C12—C13 | 2.2 (3) |
C19—Si1—C10—C9 | 21.2 (2) | C11—C10—C9—C14 | 1.1 (3) |
C18—Si1—C10—C11 | 78.69 (19) | Si1—C10—C9—C14 | 178.88 (16) |
C17—Si1—C10—C11 | −45.62 (19) | C11—C10—C9—N3 | −176.27 (16) |
C19—Si1—C10—C11 | −161.06 (16) | Si1—C10—C9—N3 | 1.6 (3) |
C5—O1—N2—N3 | −0.4 (2) | N2—N3—C9—C10 | 74.8 (2) |
C16—O11—C11—C12 | 1.0 (3) | C4—N3—C9—C10 | −108.0 (2) |
C16—O11—C11—C10 | −178.23 (17) | N2—N3—C9—C14 | −102.8 (2) |
C9—C10—C11—O11 | 177.20 (16) | C4—N3—C9—C14 | 74.3 (2) |
Si1—C10—C11—O11 | −0.8 (2) | C10—C9—C14—C13 | −0.3 (3) |
C9—C10—C11—C12 | −2.0 (3) | N3—C9—C14—C13 | 177.16 (17) |
Si1—C10—C11—C12 | 180.00 (15) | N2—O1—C5—O5 | 179.11 (19) |
O1—N2—N3—C4 | 0.8 (2) | N2—O1—C5—C4 | 0.0 (2) |
O1—N2—N3—C9 | 178.22 (15) | N3—C4—C5—O5 | −178.5 (2) |
N2—N3—C4—C5 | −0.8 (2) | Si2—C4—C5—O5 | 1.5 (4) |
C9—N3—C4—C5 | −177.93 (17) | N3—C4—C5—O1 | 0.4 (2) |
N2—N3—C4—Si2 | 179.27 (15) | Si2—C4—C5—O1 | −179.62 (14) |
C9—N3—C4—Si2 | 2.1 (3) | C15—O13—C13—C14 | 0.1 (3) |
C7—Si2—C4—N3 | 160.0 (2) | C15—O13—C13—C12 | −177.7 (2) |
C6—Si2—C4—N3 | 40.3 (2) | C9—C14—C13—O13 | −177.35 (19) |
C8—Si2—C4—N3 | −80.8 (2) | C9—C14—C13—C12 | 0.4 (3) |
C7—Si2—C4—C5 | −19.9 (3) | C11—C12—C13—O13 | 176.59 (18) |
C6—Si2—C4—C5 | −139.7 (2) | C11—C12—C13—C14 | −1.3 (3) |
C8—Si2—C4—C5 | 99.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O5i | 0.95 | 2.63 | 3.219 (3) | 120 |
C15—H15C···O5i | 0.98 | 2.67 | 3.594 (3) | 158 |
C18—H18C···O13ii | 0.98 | 2.62 | 3.549 (4) | 159 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1. |