Literature DB >> 23284407

Diphenyl(pyridin-2-yl)-phosphane selenide.

Wade L Davis1, Alfred Muller.   

Abstract

In the title compound, C(17)H(14)NPSe, the P atom has a distorted tetra-hedral environment resulting in an effective cone angle of 163°. In the crystal, C-H⋯Se/N/π inter-actions are observed.

Entities:  

Year:  2012        PMID： 23284407      PMCID： PMC3515180          DOI： 10.1107/S160053681204007X

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


Related literature

For background to phospho­rus- and selenium-containing ligands, see: Muller et al. (2006 ▶, 2008 ▶). For the free phosphine of the title compound, see: Charland et al. (1989 ▶). For background on cone angles, see: Otto (2001 ▶); Tolman (1977 ▶). For details of the conformational fit of the two mol­ecules using Mercury, see: Macrae et al. (2008 ▶); Weng et al. (2008a ▶,b ▶).

Experimental

Crystal data

C17H14NPSe M = 342.22 Orthorhombic, a = 8.8092 (4) Å b = 9.4066 (4) Å c = 18.2661 (7) Å V = 1513.61 (11) Å3 Z = 4 Cu Kα radiation μ = 4.25 mm−1 T = 100 K 0.24 × 0.17 × 0.12 mm

Data collection

Bruker APEX DUO 4K-CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.429, T max = 0.629 6004 measured reflections 2501 independent reflections 2461 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.021 wR(F 2) = 0.053 S = 0.87 2501 reflections 181 parameters H-atom parameters constrained Δρmax = 0.43 e Å−3 Δρmin = −0.27 e Å−3 Absolute structure: Flack (1983 ▶), with 992 Friedel pairs Flack parameter: 0.053 (19) Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); 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: publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 1999 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204007X/kp2438sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204007X/kp2438Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S160053681204007X/kp2438Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H14NPSeF(000) = 688
Mr = 342.22Dx = 1.502 Mg m−3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 5093 reflections
a = 8.8092 (4) Åθ = 4.8–66.6°
b = 9.4066 (4) ŵ = 4.25 mm−1
c = 18.2661 (7) ÅT = 100 K
V = 1513.61 (11) Å3Cuboid, colourless
Z = 40.24 × 0.17 × 0.12 mm
Bruker APEX DUO 4K-CCD diffractometer2501 independent reflections
Incoatec Quazar Multilayer Mirror monochromator2461 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1Rint = 0.025
φ and ω scansθmax = 66.6°, θmin = 4.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −9→10
Tmin = 0.429, Tmax = 0.629k = −3→11
6004 measured reflectionsl = −21→20
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.053w = 1/[σ2(Fo2) + (0.0288P)2 + 1.1995P] where P = (Fo2 + 2Fc2)/3
S = 0.87(Δ/σ)max < 0.001
2501 reflectionsΔρmax = 0.43 e Å−3
181 parametersΔρmin = −0.27 e Å−3
0 restraintsAbsolute structure: Flack (1983), with 992 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.053 (19)
Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 5 s/frame. A total of 287 frames were collected with a frame width of 4° covering up to θ = 66.62° with 96.7% 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
Se10.16691 (3)0.13803 (3)0.059243 (13)0.01846 (8)
P10.28195 (7)−0.00265 (7)0.12974 (3)0.01351 (13)
N10.5564 (3)−0.0376 (2)0.19118 (12)0.0211 (5)
C10.2066 (3)−0.0007 (3)0.22196 (12)0.0155 (5)
C20.2524 (3)0.1080 (3)0.26909 (13)0.0222 (6)
H20.32820.17370.25410.027*
C30.1867 (3)0.1197 (3)0.33781 (14)0.0279 (6)
H30.21850.19270.37030.034*
C40.0749 (3)0.0250 (3)0.35923 (14)0.0271 (6)
H40.02920.03410.40610.033*
C50.0295 (3)−0.0826 (3)0.31256 (14)0.0226 (6)
H5−0.0465−0.14790.32760.027*
C60.0953 (3)−0.0952 (3)0.24349 (14)0.0192 (6)
H60.0636−0.16870.21130.023*
C70.2834 (3)−0.1863 (3)0.09839 (13)0.0165 (5)
C120.2168 (3)−0.2192 (3)0.03143 (13)0.0218 (6)
H120.1654−0.14810.00410.026*
C110.2266 (3)−0.3580 (3)0.00496 (13)0.0257 (6)
H110.1802−0.382−0.04030.031*
C100.3034 (3)−0.4608 (3)0.04429 (14)0.0249 (6)
H100.3129−0.55430.02520.03*
C90.3666 (3)−0.4276 (3)0.11135 (15)0.0271 (6)
H90.417−0.4990.13890.033*
C80.3567 (3)−0.2906 (3)0.13858 (14)0.0216 (6)
H80.4001−0.26810.18480.026*
C130.4816 (3)0.0441 (3)0.14240 (13)0.0153 (5)
C170.7046 (3)−0.0092 (3)0.20170 (14)0.0222 (6)
H170.7597−0.06570.23560.027*
C160.7802 (3)0.0985 (3)0.16541 (14)0.0203 (6)
H160.88510.11460.17410.024*
C150.7021 (3)0.1817 (3)0.11670 (14)0.0221 (6)
H150.75180.25710.09170.026*
C140.5494 (3)0.1544 (3)0.10432 (13)0.0193 (5)
H140.49280.210.07060.023*
U11U22U33U12U13U23
Se10.01952 (13)0.01885 (13)0.01701 (12)0.00321 (11)−0.00156 (10)0.00276 (10)
P10.0138 (3)0.0140 (3)0.0127 (3)0.0002 (3)0.0005 (2)0.0005 (2)
N10.0168 (11)0.0207 (12)0.0257 (11)0.0009 (9)−0.0010 (9)0.0027 (9)
C10.0160 (13)0.0164 (12)0.0142 (10)0.0031 (11)−0.0007 (9)0.0023 (9)
C20.0217 (14)0.0247 (16)0.0201 (13)−0.0027 (11)0.0031 (10)−0.0015 (10)
C30.0336 (16)0.0306 (15)0.0196 (13)0.0013 (15)0.0005 (11)−0.0057 (11)
C40.0285 (16)0.0351 (17)0.0178 (13)0.0114 (13)0.0059 (11)0.0033 (11)
C50.0170 (13)0.0280 (15)0.0229 (13)0.0036 (11)0.0054 (11)0.0099 (11)
C60.0185 (13)0.0200 (15)0.0193 (12)0.0024 (11)−0.0020 (10)0.0028 (10)
C70.0141 (12)0.0161 (13)0.0194 (12)−0.0012 (10)0.0058 (10)−0.0019 (9)
C120.0256 (13)0.0230 (14)0.0167 (12)−0.0026 (12)0.0021 (10)0.0000 (10)
C110.0360 (14)0.0233 (13)0.0176 (12)−0.0096 (14)0.0010 (11)−0.0032 (11)
C100.0329 (16)0.0172 (13)0.0246 (13)−0.0034 (11)0.0103 (11)−0.0040 (10)
C90.0273 (17)0.0213 (14)0.0327 (15)0.0037 (12)0.0009 (12)0.0000 (11)
C80.0216 (14)0.0233 (13)0.0199 (12)−0.0015 (12)−0.0043 (11)−0.0036 (10)
C130.0142 (12)0.0168 (13)0.0149 (11)0.0028 (10)0.0030 (9)−0.0026 (9)
C170.0210 (14)0.0206 (13)0.0250 (13)−0.0015 (13)−0.0041 (10)0.0007 (11)
C160.0140 (12)0.0222 (15)0.0248 (13)−0.0042 (11)0.0014 (10)−0.0057 (10)
C150.0191 (14)0.0244 (14)0.0227 (12)−0.0061 (11)0.0025 (10)0.0026 (10)
C140.0185 (12)0.0213 (14)0.0179 (12)0.0000 (12)−0.0007 (9)0.0002 (10)
Se1—P12.1063 (6)C7—C121.391 (3)
P1—C11.811 (2)C12—C111.395 (4)
P1—C71.820 (2)C12—H120.95
P1—C131.828 (3)C11—C101.381 (4)
N1—C131.349 (3)C11—H110.95
N1—C171.347 (3)C10—C91.381 (4)
C1—C61.380 (4)C10—H100.95
C1—C21.397 (4)C9—C81.384 (4)
C2—C31.387 (4)C9—H90.95
C2—H20.95C8—H80.95
C3—C41.384 (4)C13—C141.384 (4)
C3—H30.95C17—C161.381 (4)
C4—C51.382 (4)C17—H170.95
C4—H40.95C16—C151.370 (4)
C5—C61.393 (4)C16—H160.95
C5—H50.95C15—C141.388 (4)
C6—H60.95C15—H150.95
C7—C81.385 (4)C14—H140.95
C1—P1—C7107.75 (11)C7—C12—H12120.4
C1—P1—C13103.46 (11)C11—C12—H12120.4
C7—P1—C13105.15 (11)C10—C11—C12120.3 (2)
C1—P1—Se1112.71 (8)C10—C11—H11119.8
C7—P1—Se1114.04 (9)C12—C11—H11119.8
C13—P1—Se1112.90 (8)C11—C10—C9120.0 (2)
C13—N1—C17117.0 (2)C11—C10—H10120
C6—C1—C2120.1 (2)C9—C10—H10120
C6—C1—P1121.27 (19)C10—C9—C8120.3 (3)
C2—C1—P1118.34 (19)C10—C9—H9119.9
C3—C2—C1119.7 (2)C8—C9—H9119.9
C3—C2—H2120.2C7—C8—C9119.9 (2)
C1—C2—H2120.2C7—C8—H8120.1
C4—C3—C2120.2 (3)C9—C8—H8120.1
C4—C3—H3119.9N1—C13—C14123.3 (2)
C2—C3—H3119.9N1—C13—P1114.59 (18)
C3—C4—C5120.1 (2)C14—C13—P1122.12 (19)
C3—C4—H4119.9N1—C17—C16123.0 (2)
C5—C4—H4119.9N1—C17—H17118.5
C4—C5—C6120.1 (3)C16—C17—H17118.5
C4—C5—H5120C15—C16—C17119.2 (2)
C6—C5—H5120C15—C16—H16120.4
C1—C6—C5119.9 (2)C17—C16—H16120.4
C1—C6—H6120.1C16—C15—C14119.1 (2)
C5—C6—H6120.1C16—C15—H15120.4
C8—C7—C12120.3 (2)C14—C15—H15120.4
C8—C7—P1120.58 (19)C13—C14—C15118.3 (2)
C12—C7—P1119.0 (2)C13—C14—H14120.8
C7—C12—C11119.1 (3)C15—C14—H14120.8
C7—P1—C1—C6−34.1 (2)P1—C7—C12—C11175.8 (2)
C13—P1—C1—C6−145.1 (2)C7—C12—C11—C10−1.0 (4)
Se1—P1—C1—C692.6 (2)C12—C11—C10—C92.2 (4)
C7—P1—C1—C2152.3 (2)C11—C10—C9—C8−1.7 (4)
C13—P1—C1—C241.3 (2)C12—C7—C8—C91.4 (4)
Se1—P1—C1—C2−81.0 (2)P1—C7—C8—C9−175.2 (2)
C6—C1—C2—C30.7 (4)C10—C9—C8—C7−0.1 (4)
P1—C1—C2—C3174.4 (2)C17—N1—C13—C14−0.7 (4)
C1—C2—C3—C4−0.8 (4)C17—N1—C13—P1178.94 (19)
C2—C3—C4—C50.8 (4)C1—P1—C13—N153.4 (2)
C3—C4—C5—C6−0.6 (4)C7—P1—C13—N1−59.5 (2)
C2—C1—C6—C5−0.5 (4)Se1—P1—C13—N1175.59 (16)
P1—C1—C6—C5−174.0 (2)C1—P1—C13—C14−126.9 (2)
C4—C5—C6—C10.5 (4)C7—P1—C13—C14120.2 (2)
C1—P1—C7—C8−55.0 (2)Se1—P1—C13—C14−4.7 (2)
C13—P1—C7—C854.9 (2)C13—N1—C17—C160.3 (4)
Se1—P1—C7—C8179.09 (18)N1—C17—C16—C150.5 (4)
C1—P1—C7—C12128.4 (2)C17—C16—C15—C14−0.9 (4)
C13—P1—C7—C12−121.7 (2)N1—C13—C14—C150.4 (4)
Se1—P1—C7—C122.5 (2)P1—C13—C14—C15−179.30 (19)
C8—C7—C12—C11−0.8 (4)C16—C15—C14—C130.5 (4)
D—H···AD—HH···AD···AD—H···A
C12—H12···Se10.952.873.427 (3)118
C8—H8···N10.952.573.111 (3)116
C14—H14···Se10.952.963.472 (2)115
C5—H5···Se1i0.953.073.923 (3)150
C16—H16···Se1ii0.953.263.938 (3)130
C11—H11···Cg1iii0.952.773.630 (3)151
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C12—H12⋯Se10.952.873.427 (3)118
C8—H8⋯N10.952.573.111 (3)116
C14—H14⋯Se10.952.963.472 (2)115
C5—H5⋯Se1i 0.953.073.923 (3)150
C16—H16⋯Se1ii 0.953.263.938 (3)130
C11—H11⋯Cg1iii 0.952.773.630 (3)151

Symmetry codes: (i) ; (ii) ; (iii) .

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