Literature DB >> 21522797

Bis(2-meth-oxy-phen-yl)(phen-yl)phosphine selenide.

Alfred Muller1.   

Abstract

The title compound, C(20)H(19)O(2)PSe or SePPh(2-OMe-C(6)H(3))(2), crystallizes with two distinct orientations for the meth-oxy groups. The Se=P bond is 2.1170 (7) Å and the cone angle is 176.0°. Intra-molecular C-H⋯Se inter-actions occur. In the crystal, mol-ecules are linked by inter-molecular C-H⋯Se inter-actions.

Entities:  

Year:  2010        PMID： 21522797      PMCID： PMC3050330          DOI： 10.1107/S1600536810051317

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For bond-length data, see: Allen et al. (2002 ▶). For our study of phospho­rus ligands, see: Muller et al. (2006 ▶, 2008 ▶). For the cone angle, see: Tolman (1977 ▶). For the synthesis of ortho-substituted aryl­alkyl­phosphanes, see: Riihimäki et al. (2003 ▶).

Experimental

Crystal data

C20H19O2PSe M = 401.28 Monoclinic, a = 8.9552 (4) Å b = 13.2737 (6) Å c = 15.9593 (6) Å β = 104.885 (1)° V = 1833.40 (14) Å3 Z = 4 Mo Kα radiation μ = 2.14 mm−1 T = 100 K 0.1 × 0.07 × 0.06 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.814, T max = 0.882 37384 measured reflections 5078 independent reflections 3483 reflections with I > 2σ(I) R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.096 S = 1.05 5078 reflections 219 parameters H-atom parameters constrained Δρmax = 0.66 e Å−3 Δρmin = −0.56 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051317/kp2295sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051317/kp2295Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H19O2PSeF(000) = 816
Mr = 401.28Dx = 1.454 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7311 reflections
a = 8.9552 (4) Åθ = 2.4–28.7°
b = 13.2737 (6) ŵ = 2.14 mm−1
c = 15.9593 (6) ÅT = 100 K
β = 104.885 (1)°Cuboid, colourless
V = 1833.40 (14) Å30.1 × 0.07 × 0.06 mm
Z = 4
Bruker X8 APEXII 4K Kappa CCD diffractometer5078 independent reflections
graphite3483 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1Rint = 0.068
ω and φ scansθmax = 29.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −12→12
Tmin = 0.814, Tmax = 0.882k = −18→18
37384 measured reflectionsl = −21→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0352P)2 + 1.667P] where P = (Fo2 + 2Fc2)/3
5078 reflections(Δ/σ)max = 0.001
219 parametersΔρmax = 0.66 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 20 s/frame. A total of 1897 frames were collected with a frame width of 0.5° covering up to θ = 29.48° with 99.6% completeness accomplished.
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.
xyzUiso*/Ueq
P10.79534 (8)0.29050 (5)0.06864 (4)0.02021 (14)
Se10.73477 (4)0.42323 (2)0.125712 (17)0.02827 (9)
C110.6822 (3)0.27995 (19)−0.04376 (16)0.0203 (5)
C120.7089 (3)0.2045 (2)−0.09973 (16)0.0233 (5)
C130.6251 (3)0.2023 (2)−0.18633 (17)0.0308 (6)
H130.64370.1511−0.2240.037*
C140.5148 (4)0.2752 (3)−0.21685 (19)0.0377 (7)
H140.45770.2739−0.27590.045*
C150.4862 (3)0.3496 (2)−0.16343 (18)0.0338 (7)
H150.40950.399−0.18540.041*
C160.5697 (3)0.3522 (2)−0.07726 (16)0.0248 (6)
H160.54990.4041−0.04050.03*
O10.8187 (2)0.13463 (15)−0.06510 (12)0.0325 (5)
C10.8732 (4)0.0704 (2)−0.1232 (2)0.0415 (8)
H1A0.79330.0209−0.14870.062*
H1B0.96680.0353−0.09130.062*
H1C0.89670.1112−0.16940.062*
C210.7630 (3)0.17564 (19)0.12269 (17)0.0237 (6)
C220.8553 (3)0.1529 (2)0.20616 (17)0.0265 (6)
C230.8299 (4)0.0648 (2)0.2478 (2)0.0374 (7)
H230.89430.04840.30330.045*
C240.7099 (4)0.0011 (2)0.2076 (2)0.0439 (8)
H240.6929−0.05920.23590.053*
C250.6152 (4)0.0241 (2)0.1272 (2)0.0400 (8)
H250.5316−0.01890.10090.048*
C260.6430 (3)0.1103 (2)0.08520 (19)0.0300 (6)
H260.57870.12540.02940.036*
O20.9673 (2)0.22128 (15)0.24085 (12)0.0317 (5)
C21.0661 (4)0.2012 (3)0.32533 (19)0.0404 (8)
H2A1.00430.19970.36790.061*
H2B1.14440.25430.34090.061*
H2C1.1170.13590.32490.061*
C310.9970 (3)0.2904 (2)0.06549 (16)0.0235 (5)
C321.0691 (3)0.3820 (2)0.05993 (17)0.0307 (6)
H321.01430.44330.05970.037*
C331.2217 (4)0.3836 (3)0.0548 (2)0.0405 (8)
H331.27040.44610.04990.049*
C341.3027 (4)0.2952 (3)0.05663 (19)0.0413 (8)
H341.4070.29680.05320.05*
C351.2326 (4)0.2042 (3)0.0634 (2)0.0387 (7)
H351.28870.14320.06480.046*
C361.0799 (3)0.2014 (2)0.06837 (18)0.0302 (6)
H361.03210.13860.07370.036*
U11U22U33U12U13U23
P10.0238 (3)0.0198 (3)0.0160 (3)−0.0016 (3)0.0031 (3)0.0015 (2)
Se10.04196 (18)0.02334 (14)0.02004 (13)0.00041 (13)0.00894 (11)−0.00166 (11)
C110.0204 (13)0.0229 (12)0.0172 (12)−0.0029 (10)0.0042 (10)0.0016 (10)
C120.0245 (14)0.0251 (13)0.0207 (13)−0.0018 (11)0.0066 (11)0.0018 (10)
C130.0346 (16)0.0380 (16)0.0201 (13)−0.0036 (13)0.0075 (12)−0.0070 (12)
C140.0349 (17)0.055 (2)0.0203 (14)0.0018 (15)0.0012 (12)−0.0016 (14)
C150.0277 (15)0.0454 (18)0.0257 (14)0.0090 (13)0.0021 (12)0.0057 (13)
C160.0237 (14)0.0315 (14)0.0197 (12)0.0023 (11)0.0066 (10)0.0019 (11)
O10.0420 (12)0.0289 (11)0.0252 (10)0.0084 (9)0.0059 (9)−0.0014 (8)
C10.054 (2)0.0318 (16)0.0398 (18)0.0110 (15)0.0138 (15)−0.0044 (14)
C210.0283 (15)0.0211 (12)0.0219 (13)−0.0011 (10)0.0068 (11)0.0023 (10)
C220.0294 (15)0.0259 (14)0.0240 (13)−0.0015 (12)0.0062 (11)0.0026 (11)
C230.0465 (19)0.0331 (16)0.0324 (16)0.0027 (14)0.0097 (14)0.0134 (13)
C240.064 (2)0.0269 (15)0.0427 (19)−0.0082 (16)0.0174 (17)0.0090 (14)
C250.049 (2)0.0314 (16)0.0401 (18)−0.0156 (14)0.0119 (15)0.0000 (13)
C260.0355 (17)0.0276 (14)0.0271 (14)−0.0092 (12)0.0083 (12)−0.0004 (11)
O20.0335 (11)0.0362 (11)0.0200 (9)−0.0051 (9)−0.0031 (8)0.0062 (8)
C20.0351 (18)0.051 (2)0.0277 (16)0.0066 (15)−0.0059 (13)0.0060 (14)
C310.0256 (14)0.0280 (14)0.0153 (12)−0.0040 (11)0.0021 (10)0.0015 (10)
C320.0339 (16)0.0315 (15)0.0238 (14)−0.0094 (12)0.0024 (12)0.0050 (12)
C330.0368 (18)0.052 (2)0.0302 (16)−0.0214 (16)0.0039 (14)0.0105 (14)
C340.0243 (15)0.070 (2)0.0283 (16)−0.0084 (16)0.0037 (12)0.0134 (16)
C350.0276 (16)0.053 (2)0.0331 (16)0.0055 (15)0.0036 (13)0.0103 (15)
C360.0261 (15)0.0331 (15)0.0293 (15)−0.0013 (12)0.0031 (12)0.0044 (12)
P1—C211.811 (3)C23—C241.388 (5)
P1—C311.820 (3)C23—H230.95
P1—C111.825 (3)C24—C251.379 (5)
P1—Se12.1170 (7)C24—H240.95
C11—C161.395 (4)C25—C261.381 (4)
C11—C121.403 (4)C25—H250.95
C12—O11.361 (3)C26—H260.95
C12—C131.393 (4)O2—C21.435 (3)
C13—C141.379 (4)C2—H2A0.98
C13—H130.95C2—H2B0.98
C14—C151.370 (4)C2—H2C0.98
C14—H140.95C31—C321.389 (4)
C15—C161.387 (4)C31—C361.390 (4)
C15—H150.95C32—C331.390 (4)
C16—H160.95C32—H320.95
O1—C11.435 (3)C33—C341.376 (5)
C1—H1A0.98C33—H330.95
C1—H1B0.98C34—C351.378 (5)
C1—H1C0.98C34—H340.95
C21—C261.391 (4)C35—C361.390 (4)
C21—C221.408 (4)C35—H350.95
C22—O21.361 (3)C36—H360.95
C22—C231.392 (4)
C21—P1—C31107.09 (12)C24—C23—C22119.6 (3)
C21—P1—C11106.69 (12)C24—C23—H23120.2
C31—P1—C11106.10 (11)C22—C23—H23120.2
C21—P1—Se1113.94 (9)C25—C24—C23120.8 (3)
C31—P1—Se1112.21 (9)C25—C24—H24119.6
C11—P1—Se1110.36 (9)C23—C24—H24119.6
C16—C11—C12118.1 (2)C24—C25—C26119.4 (3)
C16—C11—P1119.21 (19)C24—C25—H25120.3
C12—C11—P1122.6 (2)C26—C25—H25120.3
O1—C12—C13122.5 (2)C25—C26—C21121.6 (3)
O1—C12—C11116.8 (2)C25—C26—H26119.2
C13—C12—C11120.7 (2)C21—C26—H26119.2
C14—C13—C12119.3 (3)C22—O2—C2118.1 (2)
C14—C13—H13120.3O2—C2—H2A109.5
C12—C13—H13120.3O2—C2—H2B109.5
C15—C14—C13121.1 (3)H2A—C2—H2B109.5
C15—C14—H14119.4O2—C2—H2C109.5
C13—C14—H14119.4H2A—C2—H2C109.5
C14—C15—C16119.8 (3)H2B—C2—H2C109.5
C14—C15—H15120.1C32—C31—C36119.5 (3)
C16—C15—H15120.1C32—C31—P1118.9 (2)
C15—C16—C11121.0 (3)C36—C31—P1121.6 (2)
C15—C16—H16119.5C31—C32—C33119.9 (3)
C11—C16—H16119.5C31—C32—H32120.1
C12—O1—C1118.2 (2)C33—C32—H32120.1
O1—C1—H1A109.5C34—C33—C32120.4 (3)
O1—C1—H1B109.5C34—C33—H33119.8
H1A—C1—H1B109.5C32—C33—H33119.8
O1—C1—H1C109.5C33—C34—C35120.1 (3)
H1A—C1—H1C109.5C33—C34—H34120
H1B—C1—H1C109.5C35—C34—H34120
C26—C21—C22118.3 (2)C34—C35—C36120.2 (3)
C26—C21—P1121.3 (2)C34—C35—H35119.9
C22—C21—P1120.3 (2)C36—C35—H35119.9
O2—C22—C23124.1 (2)C35—C36—C31120.0 (3)
O2—C22—C21115.7 (2)C35—C36—H36120
C23—C22—C21120.2 (3)C31—C36—H36120
C21—P1—C11—C16121.2 (2)P1—C21—C22—O2−0.7 (3)
C31—P1—C11—C16−124.8 (2)C26—C21—C22—C232.7 (4)
Se1—P1—C11—C16−3.0 (2)P1—C21—C22—C23179.7 (2)
C21—P1—C11—C12−62.0 (2)O2—C22—C23—C24178.4 (3)
C31—P1—C11—C1251.9 (2)C21—C22—C23—C24−2.1 (5)
Se1—P1—C11—C12173.69 (19)C22—C23—C24—C25−0.2 (5)
C16—C11—C12—O1−179.6 (2)C23—C24—C25—C261.8 (5)
P1—C11—C12—O13.6 (3)C24—C25—C26—C21−1.1 (5)
C16—C11—C12—C130.1 (4)C22—C21—C26—C25−1.2 (4)
P1—C11—C12—C13−176.6 (2)P1—C21—C26—C25−178.1 (2)
O1—C12—C13—C14179.6 (3)C23—C22—O2—C20.3 (4)
C11—C12—C13—C14−0.1 (4)C21—C22—O2—C2−179.2 (2)
C12—C13—C14—C15−0.1 (5)C21—P1—C31—C32−154.9 (2)
C13—C14—C15—C160.3 (5)C11—P1—C31—C3291.4 (2)
C14—C15—C16—C11−0.3 (4)Se1—P1—C31—C32−29.2 (2)
C12—C11—C16—C150.1 (4)C21—P1—C31—C3625.2 (2)
P1—C11—C16—C15177.0 (2)C11—P1—C31—C36−88.5 (2)
C13—C12—O1—C113.8 (4)Se1—P1—C31—C36150.9 (2)
C11—C12—O1—C1−166.5 (2)C36—C31—C32—C331.9 (4)
C31—P1—C21—C26−127.6 (2)P1—C31—C32—C33−178.0 (2)
C11—P1—C21—C26−14.3 (3)C31—C32—C33—C34−1.1 (4)
Se1—P1—C21—C26107.7 (2)C32—C33—C34—C350.2 (5)
C31—P1—C21—C2255.5 (2)C33—C34—C35—C360.1 (5)
C11—P1—C21—C22168.8 (2)C34—C35—C36—C310.7 (4)
Se1—P1—C21—C22−69.2 (2)C32—C31—C36—C35−1.6 (4)
C26—C21—C22—O2−177.7 (2)P1—C31—C36—C35178.2 (2)
D—H···AD—HH···AD···AD—H···A
C13—H13···Se1i0.952.93.775 (3)154
C15—H15···Se1ii0.952.963.740 (3)140
C16—H16···Se10.952.753.333 (3)120
C32—H32···Se10.952.973.462 (3)114
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C13—H13⋯Se1i0.952.93.775 (3)154
C15—H15⋯Se1ii0.952.963.740 (3)140
C16—H16⋯Se10.952.753.333 (3)120
C32—H32⋯Se10.952.973.462 (3)114

Symmetry codes: (i) ; (ii) .

  3 in total

1.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Rapid phosphorus(III) ligand evaluation utilising potassium selenocyanate.

Authors:  Alfred Muller; Stefanus Otto; Andreas Roodt
Journal:  Dalton Trans       Date:  2007-11-16       Impact factor: 4.390
  3 in total

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