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Bis(triphenyl­silyl)selenide, [(C6H5)3Si]2Se or C36H30SeSi2, exists in the solid state as monomeric angular mol­ecules. Si-Se-Si angles of 111.56 (3) and 109.45 (3)° are found in the two independent mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023275/hg6210sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023275/hg6210Isup2.hkl
Contains datablock I

CCDC reference: 282378

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.025
  • wR factor = 0.060
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.58
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 6362 Count of symmetry unique reflns 3648 Completeness (_total/calc) 174.40% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2714 Fraction of Friedel pairs measured 0.744 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Bis(triphenylsilyl)selenide top
Crystal data top
C36H30SeSi2F(000) = 1232
Mr = 597.74Dx = 1.342 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 5506 reflections
a = 18.159 (2) Åθ = 2.3–28.3°
b = 7.8122 (9) ŵ = 1.37 mm1
c = 21.777 (3) ÅT = 100 K
β = 106.724 (2)°Plate, colorless
V = 2958.6 (6) Å30.35 × 0.22 × 0.11 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6362 independent reflections
Radiation source: fine-focus sealed tube6027 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 2323
Tmin = 0.713, Tmax = 0.867k = 1010
12735 measured reflectionsl = 2827
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.060 w = 1/[σ2(Fo2) + (0.0074P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
6362 reflectionsΔρmax = 0.60 e Å3
353 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983), 2714 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.016 (5)
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.

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, andR– factors based on ALL data will be even larger. H-atoms were placed in calculated positions (C—H = 0.95 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached carbon atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se10.00000.39973 (3)0.50000.02175 (8)
Si10.06770 (3)0.56513 (7)0.58472 (3)0.01730 (13)
C10.00487 (11)0.7015 (3)0.61902 (10)0.0199 (4)
C20.06167 (12)0.6372 (3)0.62994 (11)0.0282 (5)
H20.07680.52250.61830.034*
C30.10623 (13)0.7384 (4)0.65760 (12)0.0357 (6)
H30.15120.69210.66510.043*
C40.08590 (12)0.9052 (3)0.67429 (10)0.0334 (5)
H40.11670.97370.69330.040*
C50.02050 (13)0.9729 (3)0.66330 (11)0.0321 (5)
H50.00621.08830.67440.039*
C60.02409 (11)0.8715 (3)0.63596 (10)0.0263 (5)
H60.06900.91880.62850.032*
C70.14200 (11)0.7016 (3)0.56436 (9)0.0173 (4)
C80.12083 (11)0.8400 (3)0.52248 (9)0.0227 (4)
H80.06780.86300.50340.027*
C90.17467 (12)0.9444 (3)0.50798 (10)0.0269 (5)
H90.15851.03680.47890.032*
C100.25275 (11)0.9146 (3)0.53588 (9)0.0258 (4)
H100.29010.98600.52590.031*
C110.27526 (11)0.7800 (3)0.57821 (10)0.0230 (4)
H110.32840.76010.59810.028*
C120.22087 (11)0.6733 (3)0.59196 (9)0.0208 (4)
H120.23740.57980.62050.025*
C130.11573 (10)0.3961 (3)0.64357 (9)0.0187 (4)
C140.15597 (11)0.2618 (3)0.62455 (9)0.0210 (4)
H140.15820.25740.58150.025*
C150.19232 (11)0.1361 (3)0.66727 (10)0.0229 (4)
H150.21870.04590.65340.027*
C160.19025 (12)0.1416 (3)0.73042 (10)0.0269 (5)
H160.21580.05630.76000.032*
C170.15076 (13)0.2719 (3)0.75004 (10)0.0280 (5)
H170.14890.27520.79320.034*
C180.11387 (11)0.3979 (3)0.70732 (9)0.0242 (4)
H180.08700.48660.72160.029*
Se20.50000.60457 (3)1.00000.02615 (8)
Si20.45006 (3)0.43493 (8)0.91179 (3)0.02013 (13)
C190.41104 (12)0.5991 (3)0.84798 (9)0.0219 (4)
C200.33549 (12)0.5882 (3)0.80811 (9)0.0255 (5)
H200.30290.49900.81460.031*
C210.30760 (13)0.7059 (3)0.75933 (10)0.0304 (5)
H210.25600.69770.73290.037*
C220.35445 (13)0.8346 (3)0.74901 (10)0.0323 (5)
H220.33520.91400.71510.039*
C230.42959 (13)0.8489 (3)0.78774 (10)0.0293 (5)
H230.46190.93790.78060.035*
C240.45721 (12)0.7319 (3)0.83704 (9)0.0248 (4)
H240.50850.74250.86390.030*
C250.52563 (11)0.3056 (3)0.89025 (9)0.0219 (5)
C260.55354 (13)0.1549 (3)0.92358 (10)0.0321 (5)
H260.53260.11680.95650.038*
C270.61094 (13)0.0603 (3)0.90951 (11)0.0413 (6)
H270.62890.04170.93270.050*
C280.64216 (13)0.1129 (3)0.86215 (13)0.0430 (6)
H280.68260.04930.85340.052*
C290.61420 (14)0.2590 (4)0.82734 (13)0.0412 (7)
H290.63450.29440.79380.049*
C300.55667 (12)0.3540 (3)0.84138 (11)0.0305 (5)
H300.53800.45410.81720.037*
C310.37118 (12)0.2914 (3)0.92013 (9)0.0213 (4)
C320.36184 (12)0.1287 (3)0.89219 (10)0.0278 (5)
H320.39740.09040.87060.033*
C330.30203 (13)0.0221 (3)0.89527 (10)0.0302 (5)
H330.29660.08770.87570.036*
C340.25001 (12)0.0767 (3)0.92721 (10)0.0294 (5)
H340.20870.00470.92950.035*
C350.25895 (12)0.2368 (3)0.95570 (10)0.0295 (5)
H350.22400.27440.97800.035*
C360.31849 (12)0.3419 (3)0.95180 (10)0.0255 (5)
H360.32360.45180.97130.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.02461 (14)0.01514 (16)0.02059 (15)0.0000.00130 (11)0.000
Si10.0169 (2)0.0157 (3)0.0183 (3)0.0005 (2)0.0035 (2)0.0000 (2)
C10.0186 (10)0.0206 (11)0.0195 (10)0.0007 (8)0.0041 (8)0.0024 (8)
C20.0243 (11)0.0195 (11)0.0430 (14)0.0000 (9)0.0130 (10)0.0039 (10)
C30.0257 (11)0.0385 (15)0.0504 (15)0.0036 (11)0.0231 (11)0.0098 (13)
C40.0318 (11)0.0396 (14)0.0329 (12)0.0133 (11)0.0157 (10)0.0013 (11)
C50.0320 (12)0.0279 (12)0.0358 (13)0.0009 (10)0.0089 (10)0.0075 (10)
C60.0205 (9)0.0263 (12)0.0326 (12)0.0041 (8)0.0087 (9)0.0059 (9)
C70.0190 (9)0.0170 (10)0.0171 (10)0.0021 (8)0.0071 (8)0.0051 (8)
C80.0197 (9)0.0267 (11)0.0197 (10)0.0015 (8)0.0025 (8)0.0009 (9)
C90.0335 (11)0.0262 (12)0.0197 (10)0.0060 (9)0.0057 (9)0.0025 (8)
C100.0278 (10)0.0295 (12)0.0227 (11)0.0088 (10)0.0111 (8)0.0047 (10)
C110.0175 (9)0.0272 (11)0.0247 (11)0.0018 (9)0.0068 (8)0.0063 (9)
C120.0221 (10)0.0188 (10)0.0213 (10)0.0010 (8)0.0060 (8)0.0032 (8)
C130.0172 (8)0.0174 (10)0.0203 (10)0.0043 (9)0.0036 (7)0.0004 (9)
C140.0208 (9)0.0203 (10)0.0209 (10)0.0022 (8)0.0044 (8)0.0014 (8)
C150.0204 (10)0.0192 (10)0.0273 (11)0.0000 (8)0.0040 (8)0.0022 (8)
C160.0267 (11)0.0222 (11)0.0266 (11)0.0015 (9)0.0006 (9)0.0051 (9)
C170.0371 (12)0.0279 (12)0.0183 (11)0.0024 (10)0.0068 (9)0.0010 (9)
C180.0271 (10)0.0194 (10)0.0254 (11)0.0005 (9)0.0066 (8)0.0028 (9)
Se20.04439 (19)0.01652 (17)0.01547 (15)0.0000.00531 (13)0.000
Si20.0247 (3)0.0202 (3)0.0144 (3)0.0046 (2)0.0038 (2)0.0001 (2)
C190.0277 (10)0.0233 (11)0.0160 (10)0.0070 (10)0.0083 (8)0.0008 (9)
C200.0265 (10)0.0316 (12)0.0197 (10)0.0081 (9)0.0088 (8)0.0017 (9)
C210.0292 (12)0.0406 (14)0.0194 (11)0.0147 (11)0.0036 (9)0.0005 (10)
C220.0447 (14)0.0316 (13)0.0200 (11)0.0202 (11)0.0083 (10)0.0059 (10)
C230.0433 (13)0.0227 (11)0.0246 (11)0.0075 (10)0.0144 (10)0.0028 (9)
C240.0295 (11)0.0242 (11)0.0192 (10)0.0045 (9)0.0047 (8)0.0000 (8)
C250.0216 (10)0.0210 (11)0.0191 (10)0.0018 (9)0.0005 (8)0.0093 (8)
C260.0359 (12)0.0335 (13)0.0211 (11)0.0121 (10)0.0008 (9)0.0039 (9)
C270.0388 (13)0.0373 (14)0.0338 (13)0.0193 (11)0.0121 (11)0.0133 (11)
C280.0209 (11)0.0446 (15)0.0603 (17)0.0038 (11)0.0064 (11)0.0283 (14)
C290.0348 (13)0.0380 (15)0.0589 (17)0.0074 (12)0.0262 (13)0.0155 (14)
C300.0288 (11)0.0251 (12)0.0404 (14)0.0051 (9)0.0143 (10)0.0074 (10)
C310.0264 (10)0.0202 (11)0.0155 (10)0.0061 (9)0.0033 (8)0.0015 (8)
C320.0343 (12)0.0288 (12)0.0222 (11)0.0021 (10)0.0112 (9)0.0032 (9)
C330.0401 (13)0.0262 (12)0.0237 (11)0.0038 (10)0.0079 (10)0.0035 (9)
C340.0270 (11)0.0371 (14)0.0217 (11)0.0018 (10)0.0033 (9)0.0086 (10)
C350.0280 (11)0.0355 (13)0.0268 (12)0.0119 (10)0.0107 (9)0.0069 (10)
C360.0322 (11)0.0198 (10)0.0242 (11)0.0090 (9)0.0077 (9)0.0037 (9)
Geometric parameters (Å, º) top
Se1—Si12.2976 (6)Se2—Si22.2947 (6)
Si1—C11.867 (2)Si2—C311.869 (2)
Si1—C71.870 (2)Si2—C251.869 (2)
Si1—C131.872 (2)Si2—C191.874 (2)
C1—C21.391 (3)C19—C241.397 (3)
C1—C61.395 (3)C19—C201.399 (3)
C2—C31.387 (3)C20—C211.386 (3)
C2—H20.9500C20—H200.9500
C3—C41.374 (4)C21—C221.377 (3)
C3—H30.9500C21—H210.9500
C4—C51.382 (3)C22—C231.387 (3)
C4—H40.9500C22—H220.9500
C5—C61.384 (3)C23—C241.389 (3)
C5—H50.9500C23—H230.9500
C6—H60.9500C24—H240.9500
C7—C81.395 (3)C25—C301.392 (3)
C7—C121.402 (3)C25—C261.400 (3)
C8—C91.378 (3)C26—C271.382 (3)
C8—H80.9500C26—H260.9500
C9—C101.392 (3)C27—C281.375 (4)
C9—H90.9500C27—H270.9500
C10—C111.380 (3)C28—C291.384 (4)
C10—H100.9500C28—H280.9500
C11—C121.389 (3)C29—C301.385 (3)
C11—H110.9500C29—H290.9500
C12—H120.9500C30—H300.9500
C13—C181.398 (3)C31—C361.388 (3)
C13—C141.407 (3)C31—C321.398 (3)
C14—C151.382 (3)C32—C331.386 (3)
C14—H140.9500C32—H320.9500
C15—C161.387 (3)C33—C341.391 (3)
C15—H150.9500C33—H330.9500
C16—C171.381 (3)C34—C351.385 (3)
C16—H160.9500C34—H340.9500
C17—C181.387 (3)C35—C361.379 (3)
C17—H170.9500C35—H350.9500
C18—H180.9500C36—H360.9500
Si1i—Se1—Si1111.56 (3)Si2ii—Se2—Si2109.45 (3)
C1—Si1—C7109.58 (10)C31—Si2—C25109.79 (10)
C1—Si1—C13110.28 (9)C31—Si2—C19110.24 (9)
C7—Si1—C13109.79 (9)C25—Si2—C19109.38 (9)
C1—Si1—Se1113.26 (7)C31—Si2—Se2113.25 (7)
C7—Si1—Se1112.71 (6)C25—Si2—Se2112.36 (7)
C13—Si1—Se1100.91 (7)C19—Si2—Se2101.52 (7)
C2—C1—C6117.51 (19)C24—C19—C20117.95 (19)
C2—C1—Si1121.55 (17)C24—C19—Si2121.16 (16)
C6—C1—Si1120.92 (15)C20—C19—Si2120.84 (17)
C3—C2—C1120.8 (2)C21—C20—C19120.8 (2)
C3—C2—H2119.6C21—C20—H20119.6
C1—C2—H2119.6C19—C20—H20119.6
C4—C3—C2120.6 (2)C22—C21—C20120.2 (2)
C4—C3—H3119.7C22—C21—H21119.9
C2—C3—H3119.7C20—C21—H21119.9
C3—C4—C5119.7 (2)C21—C22—C23120.4 (2)
C3—C4—H4120.1C21—C22—H22119.8
C5—C4—H4120.1C23—C22—H22119.8
C4—C5—C6119.6 (2)C22—C23—C24119.3 (2)
C4—C5—H5120.2C22—C23—H23120.3
C6—C5—H5120.2C24—C23—H23120.3
C5—C6—C1121.7 (2)C23—C24—C19121.3 (2)
C5—C6—H6119.1C23—C24—H24119.3
C1—C6—H6119.1C19—C24—H24119.3
C8—C7—C12117.22 (18)C30—C25—C26117.3 (2)
C8—C7—Si1120.99 (15)C30—C25—Si2122.23 (17)
C12—C7—Si1121.76 (16)C26—C25—Si2120.47 (17)
C9—C8—C7121.88 (19)C27—C26—C25121.2 (2)
C9—C8—H8119.1C27—C26—H26119.4
C7—C8—H8119.1C25—C26—H26119.4
C8—C9—C10120.1 (2)C28—C27—C26120.4 (2)
C8—C9—H9119.9C28—C27—H27119.8
C10—C9—H9119.9C26—C27—H27119.8
C11—C10—C9119.17 (19)C27—C28—C29119.5 (2)
C11—C10—H10120.4C27—C28—H28120.3
C9—C10—H10120.4C29—C28—H28120.3
C10—C11—C12120.57 (19)C28—C29—C30120.1 (2)
C10—C11—H11119.7C28—C29—H29119.9
C12—C11—H11119.7C30—C29—H29119.9
C11—C12—C7121.00 (19)C29—C30—C25121.4 (2)
C11—C12—H12119.5C29—C30—H30119.3
C7—C12—H12119.5C25—C30—H30119.3
C18—C13—C14117.55 (19)C36—C31—C32117.4 (2)
C18—C13—Si1122.21 (16)C36—C31—Si2122.31 (17)
C14—C13—Si1120.24 (14)C32—C31—Si2120.24 (16)
C15—C14—C13121.28 (18)C33—C32—C31121.6 (2)
C15—C14—H14119.4C33—C32—H32119.2
C13—C14—H14119.4C31—C32—H32119.2
C14—C15—C16120.08 (19)C32—C33—C34119.6 (2)
C14—C15—H15120.0C32—C33—H33120.2
C16—C15—H15120.0C34—C33—H33120.2
C17—C16—C15119.6 (2)C35—C34—C33119.5 (2)
C17—C16—H16120.2C35—C34—H34120.3
C15—C16—H16120.2C33—C34—H34120.3
C16—C17—C18120.58 (19)C36—C35—C34120.2 (2)
C16—C17—H17119.7C36—C35—H35119.9
C18—C17—H17119.7C34—C35—H35119.9
C17—C18—C13120.90 (19)C35—C36—C31121.7 (2)
C17—C18—H18119.5C35—C36—H36119.1
C13—C18—H18119.5C31—C36—H36119.1
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+2.
 

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