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The title compound, C16H26N2O4Si2, is a mesoionic compound of the sydnone class. Its mol­ecular structure reveals the two planar ring fragments mutually twisted by 74.88 (10)°. The crystal packing is characterized by a one-dimensional mol­ecular array generated by C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701361X/kp2079sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701361X/kp2079Isup2.hkl
Contains datablock I

CCDC reference: 647256

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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).

3-[3,5-Dimethoxy-2-(trimethylsilyl)phenyl]-4-trimethylsilylsydnone top
Crystal data top
C16H26N2O4Si2F(000) = 784
Mr = 366.57Dx = 1.239 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8711 reflections
a = 12.5402 (12) Åθ = 2.7–30.5°
b = 8.1958 (8) ŵ = 0.20 mm1
c = 19.3421 (19) ÅT = 100 K
β = 98.786 (2)°Block, colourless
V = 1964.6 (3) Å30.53 × 0.41 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
5968 independent reflections
Radiation source: fine-focus sealed tube5726 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 30.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
h = 1717
Tmin = 0.933, Tmax = 0.968k = 1111
22233 measured reflectionsl = 2727
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-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 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.12569 (4)1.18677 (7)0.33853 (3)0.01847 (12)
Si20.41353 (5)0.76702 (7)0.33679 (3)0.02303 (14)
O110.04717 (11)0.9864 (2)0.38420 (8)0.0255 (3)
C100.14125 (15)1.0029 (2)0.39934 (10)0.0182 (3)
O10.46169 (13)1.1943 (2)0.44611 (8)0.0287 (3)
N20.36112 (15)1.1530 (2)0.46082 (10)0.0259 (4)
O130.15069 (14)0.6028 (2)0.53640 (9)0.0312 (4)
C110.04810 (16)0.9207 (2)0.41508 (10)0.0206 (4)
N30.33928 (13)1.0156 (2)0.42647 (8)0.0187 (3)
O50.58695 (13)1.0948 (2)0.38330 (9)0.0348 (4)
C40.41547 (15)0.9576 (2)0.39034 (10)0.0208 (4)
C120.05337 (17)0.7860 (3)0.45892 (10)0.0231 (4)
H120.01090.73230.46670.028*
C90.23740 (15)0.9385 (2)0.43388 (10)0.0185 (3)
C140.24769 (16)0.8057 (2)0.47910 (10)0.0218 (4)
H140.31650.76830.50070.026*
C50.49986 (17)1.0760 (3)0.40204 (11)0.0253 (4)
C130.15353 (18)0.7299 (2)0.49146 (11)0.0237 (4)
C160.14527 (17)0.9148 (3)0.39858 (12)0.0282 (4)
H16A0.15140.80340.38000.042*
H16B0.20660.97980.37630.042*
H16C0.14510.91220.44920.042*
C170.0245 (2)1.1438 (3)0.26001 (13)0.0364 (5)
H17A0.04741.13610.27370.055*
H17B0.04231.04050.23890.055*
H17C0.02531.23230.22600.055*
C180.0907 (3)1.3640 (3)0.38979 (13)0.0412 (6)
H18A0.09251.46370.36200.062*
H18B0.14301.37330.43280.062*
H18C0.01821.34910.40180.062*
C190.25108 (18)1.2342 (3)0.30142 (13)0.0319 (5)
H19A0.23591.32020.26610.048*
H19B0.27581.13590.27980.048*
H19C0.30731.27150.33890.048*
C150.2519 (2)0.5467 (3)0.57248 (16)0.0446 (7)
H15A0.29510.50270.53870.067*
H15B0.23960.46110.60570.067*
H15C0.29050.63790.59780.067*
C80.4510 (3)0.5905 (4)0.39555 (16)0.0557 (9)
H8A0.46610.49570.36770.084*
H8B0.39120.56480.42100.084*
H8C0.51540.61760.42900.084*
C70.5147 (3)0.7993 (5)0.2782 (2)0.0693 (12)
H7A0.58550.81880.30620.104*
H7B0.49410.89400.24820.104*
H7C0.51830.70220.24910.104*
C60.2783 (2)0.7327 (4)0.28539 (17)0.0479 (7)
H6A0.25570.83060.25790.072*
H6B0.22650.70960.31720.072*
H6C0.28130.63980.25380.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0208 (2)0.0176 (2)0.0166 (2)0.00019 (19)0.00188 (18)0.00105 (18)
Si20.0217 (3)0.0225 (3)0.0253 (3)0.0007 (2)0.0049 (2)0.0012 (2)
O110.0184 (6)0.0281 (8)0.0304 (8)0.0012 (6)0.0054 (5)0.0048 (6)
C100.0224 (8)0.0166 (8)0.0157 (8)0.0003 (6)0.0036 (6)0.0011 (6)
O10.0299 (8)0.0252 (8)0.0289 (8)0.0102 (6)0.0021 (6)0.0006 (6)
N20.0308 (9)0.0199 (8)0.0261 (8)0.0060 (7)0.0009 (7)0.0019 (7)
O130.0391 (9)0.0243 (8)0.0288 (8)0.0080 (7)0.0005 (6)0.0096 (6)
C110.0221 (9)0.0211 (9)0.0189 (8)0.0010 (7)0.0044 (7)0.0019 (7)
N30.0214 (7)0.0171 (7)0.0164 (7)0.0022 (6)0.0016 (5)0.0019 (6)
O50.0207 (7)0.0429 (10)0.0390 (9)0.0111 (7)0.0008 (6)0.0056 (8)
C40.0174 (8)0.0216 (9)0.0225 (9)0.0036 (7)0.0003 (6)0.0028 (7)
C120.0274 (9)0.0212 (9)0.0212 (9)0.0051 (7)0.0055 (7)0.0001 (7)
C90.0218 (8)0.0161 (8)0.0175 (8)0.0029 (6)0.0026 (6)0.0016 (6)
C140.0254 (9)0.0186 (9)0.0204 (8)0.0007 (7)0.0005 (7)0.0018 (7)
C50.0239 (9)0.0261 (10)0.0233 (9)0.0057 (8)0.0051 (7)0.0033 (8)
C130.0333 (10)0.0166 (9)0.0209 (9)0.0040 (7)0.0033 (7)0.0012 (7)
C160.0205 (9)0.0353 (12)0.0298 (10)0.0069 (8)0.0067 (8)0.0044 (9)
C170.0333 (12)0.0422 (14)0.0295 (11)0.0099 (10)0.0091 (9)0.0110 (10)
C180.0745 (19)0.0239 (11)0.0277 (11)0.0124 (12)0.0154 (12)0.0039 (9)
C190.0268 (10)0.0356 (12)0.0333 (11)0.0021 (9)0.0052 (8)0.0163 (10)
C150.0497 (15)0.0326 (13)0.0452 (15)0.0107 (11)0.0126 (12)0.0219 (12)
C80.095 (3)0.0280 (13)0.0397 (15)0.0177 (15)0.0044 (16)0.0040 (11)
C70.082 (3)0.052 (2)0.090 (3)0.0268 (18)0.064 (2)0.0308 (19)
C60.0388 (14)0.0467 (16)0.0523 (17)0.0051 (12)0.0118 (12)0.0252 (14)
Geometric parameters (Å, º) top
Si1—C181.849 (3)C14—H140.9500
Si1—C171.858 (2)C16—H16A0.9800
Si1—C191.866 (2)C16—H16B0.9800
Si1—C101.903 (2)C16—H16C0.9800
Si2—C71.845 (3)C17—H17A0.9800
Si2—C61.851 (3)C17—H17B0.9800
Si2—C81.856 (3)C17—H17C0.9800
Si2—C41.872 (2)C18—H18A0.9800
O11—C111.362 (2)C18—H18B0.9800
O11—C161.428 (2)C18—H18C0.9800
C10—C91.390 (3)C19—H19A0.9800
C10—C111.421 (3)C19—H19B0.9800
O1—N21.377 (2)C19—H19C0.9800
O1—C51.421 (3)C15—H15A0.9800
N2—N31.315 (2)C15—H15B0.9800
O13—C131.360 (2)C15—H15C0.9800
O13—C151.428 (3)C8—H8A0.9800
C11—C121.388 (3)C8—H8B0.9800
N3—C41.353 (3)C8—H8C0.9800
N3—C91.452 (2)C7—H7A0.9800
O5—C51.212 (3)C7—H7B0.9800
C4—C51.428 (3)C7—H7C0.9800
C12—C131.394 (3)C6—H6A0.9800
C12—H120.9500C6—H6B0.9800
C9—C141.390 (3)C6—H6C0.9800
C14—C131.387 (3)
C18—Si1—C17113.52 (14)O11—C16—H16C109.5
C18—Si1—C19108.98 (14)H16A—C16—H16C109.5
C17—Si1—C19103.61 (12)H16B—C16—H16C109.5
C18—Si1—C10107.53 (10)Si1—C17—H17A109.5
C17—Si1—C10110.36 (10)Si1—C17—H17B109.5
C19—Si1—C10112.93 (9)H17A—C17—H17B109.5
C7—Si2—C6110.57 (19)Si1—C17—H17C109.5
C7—Si2—C8110.8 (2)H17A—C17—H17C109.5
C6—Si2—C8109.63 (17)H17B—C17—H17C109.5
C7—Si2—C4105.55 (12)Si1—C18—H18A109.5
C6—Si2—C4110.93 (11)Si1—C18—H18B109.5
C8—Si2—C4109.34 (11)H18A—C18—H18B109.5
C11—O11—C16118.43 (17)Si1—C18—H18C109.5
C9—C10—C11113.48 (17)H18A—C18—H18C109.5
C9—C10—Si1126.65 (14)H18B—C18—H18C109.5
C11—C10—Si1119.84 (14)Si1—C19—H19A109.5
N2—O1—C5111.06 (15)Si1—C19—H19B109.5
N3—N2—O1103.45 (16)H19A—C19—H19B109.5
C13—O13—C15116.79 (18)Si1—C19—H19C109.5
O11—C11—C12122.63 (18)H19A—C19—H19C109.5
O11—C11—C10114.41 (17)H19B—C19—H19C109.5
C12—C11—C10122.96 (18)O13—C15—H15A109.5
N2—N3—C4116.92 (17)O13—C15—H15B109.5
N2—N3—C9116.17 (16)H15A—C15—H15B109.5
C4—N3—C9126.85 (16)O13—C15—H15C109.5
N3—C4—C5104.13 (18)H15A—C15—H15C109.5
N3—C4—Si2128.92 (14)H15B—C15—H15C109.5
C5—C4—Si2126.96 (16)Si2—C8—H8A109.5
C11—C12—C13119.60 (19)Si2—C8—H8B109.5
C11—C12—H12120.2H8A—C8—H8B109.5
C13—C12—H12120.2Si2—C8—H8C109.5
C10—C9—C14126.15 (18)H8A—C8—H8C109.5
C10—C9—N3119.96 (17)H8B—C8—H8C109.5
C14—C9—N3113.85 (17)Si2—C7—H7A109.5
C13—C14—C9117.37 (18)Si2—C7—H7B109.5
C13—C14—H14121.3H7A—C7—H7B109.5
C9—C14—H14121.3Si2—C7—H7C109.5
O5—C5—O1119.61 (19)H7A—C7—H7C109.5
O5—C5—C4136.0 (2)H7B—C7—H7C109.5
O1—C5—C4104.43 (18)Si2—C6—H6A109.5
O13—C13—C14124.0 (2)Si2—C6—H6B109.5
O13—C13—C12115.55 (19)H6A—C6—H6B109.5
C14—C13—C12120.42 (19)Si2—C6—H6C109.5
O11—C16—H16A109.5H6A—C6—H6C109.5
O11—C16—H16B109.5H6B—C6—H6C109.5
H16A—C16—H16B109.5
C18—Si1—C10—C999.0 (2)O11—C11—C12—C13176.91 (19)
C17—Si1—C10—C9136.68 (18)C10—C11—C12—C132.2 (3)
C19—Si1—C10—C921.2 (2)C11—C10—C9—C141.1 (3)
C18—Si1—C10—C1178.69 (19)Si1—C10—C9—C14178.88 (16)
C17—Si1—C10—C1145.62 (19)C11—C10—C9—N3176.27 (16)
C19—Si1—C10—C11161.06 (16)Si1—C10—C9—N31.6 (3)
C5—O1—N2—N30.4 (2)N2—N3—C9—C1074.8 (2)
C16—O11—C11—C121.0 (3)C4—N3—C9—C10108.0 (2)
C16—O11—C11—C10178.23 (17)N2—N3—C9—C14102.8 (2)
C9—C10—C11—O11177.20 (16)C4—N3—C9—C1474.3 (2)
Si1—C10—C11—O110.8 (2)C10—C9—C14—C130.3 (3)
C9—C10—C11—C122.0 (3)N3—C9—C14—C13177.16 (17)
Si1—C10—C11—C12180.00 (15)N2—O1—C5—O5179.11 (19)
O1—N2—N3—C40.8 (2)N2—O1—C5—C40.0 (2)
O1—N2—N3—C9178.22 (15)N3—C4—C5—O5178.5 (2)
N2—N3—C4—C50.8 (2)Si2—C4—C5—O51.5 (4)
C9—N3—C4—C5177.93 (17)N3—C4—C5—O10.4 (2)
N2—N3—C4—Si2179.27 (15)Si2—C4—C5—O1179.62 (14)
C9—N3—C4—Si22.1 (3)C15—O13—C13—C140.1 (3)
C7—Si2—C4—N3160.0 (2)C15—O13—C13—C12177.7 (2)
C6—Si2—C4—N340.3 (2)C9—C14—C13—O13177.35 (19)
C8—Si2—C4—N380.8 (2)C9—C14—C13—C120.4 (3)
C7—Si2—C4—C519.9 (3)C11—C12—C13—O13176.59 (18)
C6—Si2—C4—C5139.7 (2)C11—C12—C13—C141.3 (3)
C8—Si2—C4—C599.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O5i0.952.633.219 (3)120
C15—H15C···O5i0.982.673.594 (3)158
C18—H18C···O13ii0.982.623.549 (4)159
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+2, z+1.
 

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