Literature DB >> 23284470

[4-(Dimethyl-amino)-phen-yl]diphenyl-phosphine selenide.

Wade L Davis1, Alfred Muller.   

Abstract

In the title compound, C(20)H(20)NPSe, the P atom lies in a distorted tetra-hedral environment. The Tolman cone angle is 157° indicating steric crowding at this atom. In the crystal, weak C-H⋯Se inter-actions create linked dimeric units and C-H⋯π inter-actions are also observed.

Entities:  

Year:  2012        PMID： 23284470      PMCID： PMC3515250          DOI： 10.1107/S1600536812042602

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


Related literature

For investigations into the steric and electronic properties of phospho­rus containing ligands, see: Roodt et al. (2003 ▶); Otto & Roodt (2004 ▶); Muller et al. (2008 ▶); Cowley & Damasco (1971 ▶); Allen & Taylor (1982 ▶); Allen et al. (1985 ▶). For the free phosphine related to the title compound, see: Dreissig & Plieth (1972 ▶). For the oxide analogue of the title compound, see: Lynch et al. (2003 ▶). For the related phosphine selenide, see: Phasha et al. (2012 ▶). For cone angles, see: Tolman (1977 ▶); Otto (2001 ▶). For details on the conformational fit of mol­ecules using Mercury, see: Macrae et al. (2006 ▶); Weng et al. (2008a ▶,b ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For background on Bent’s rule, see: Bent (1961 ▶).

Experimental

Crystal data

C20H20NPSe M = 384.3 Monoclinic, a = 12.1757 (13) Å b = 10.6173 (11) Å c = 17.5211 (14) Å β = 128.098 (5)° V = 1782.5 (3) Å3 Z = 4 Mo Kα radiation μ = 2.20 mm−1 T = 100 K 0.22 × 0.11 × 0.09 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.643, T max = 0.827 31924 measured reflections 4553 independent reflections 3798 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.097 S = 1.06 4553 reflections 210 parameters H-atom parameters constrained Δρmax = 0.53 e Å−3 Δρmin = −0.72 e Å−3 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 ▶) & WinGX (Farrugia, 1999 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042602/yk2075sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042602/yk2075Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812042602/yk2075Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H20NPSeF(000) = 784
Mr = 384.3Dx = 1.432 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9940 reflections
a = 12.1757 (13) Åθ = 2.3–28.3°
b = 10.6173 (11) ŵ = 2.20 mm−1
c = 17.5211 (14) ÅT = 100 K
β = 128.098 (5)°Cuboid, colourless
V = 1782.5 (3) Å30.22 × 0.11 × 0.09 mm
Z = 4
Bruker APEX DUO 4K CCD diffractometer4553 independent reflections
Radiation source: sealed tube3798 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 8.4 pixels mm-1θmax = 28.7°, θmin = 2.1°
φ and ω scansh = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2008)k = −14→14
Tmin = 0.643, Tmax = 0.827l = −23→23
31924 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0336P)2 + 3.5217P] where P = (Fo2 + 2Fc2)/3
4553 reflections(Δ/σ)max = 0.001
210 parametersΔρmax = 0.53 e Å−3
0 restraintsΔρmin = −0.72 e Å−3
Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 20 s/frame. A total of 2352 frames were collected with a frame width of 0.5° covering up to θ = 28.66° with 99.3% completeness accomplished.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Se10.65445 (3)0.81555 (3)0.51517 (2)0.02312 (9)
P10.79548 (6)0.70500 (6)0.51220 (4)0.01475 (13)
N10.5685 (2)0.1943 (2)0.33365 (16)0.0202 (4)
C10.8477 (2)0.7754 (2)0.44440 (17)0.0158 (5)
C20.9861 (3)0.7749 (3)0.4794 (2)0.0284 (6)
H21.05720.7440.54270.034*
C31.0206 (3)0.8195 (3)0.4219 (2)0.0354 (7)
H31.11520.81930.44630.042*
C40.9182 (3)0.8642 (3)0.3296 (2)0.0236 (5)
H40.94210.89450.29060.028*
C50.7798 (3)0.8645 (3)0.29429 (19)0.0222 (5)
H50.70890.8940.23050.027*
C60.7448 (3)0.8218 (3)0.35178 (19)0.0211 (5)
H60.65040.82430.32780.025*
C70.9584 (2)0.6739 (2)0.63238 (17)0.0160 (5)
C81.0104 (3)0.5520 (2)0.66278 (18)0.0179 (5)
H80.96050.48270.62050.021*
C91.1364 (3)0.5315 (3)0.75581 (19)0.0229 (5)
H91.17130.44840.7770.027*
C101.2095 (3)0.6329 (3)0.81646 (19)0.0266 (6)
H101.29530.61910.87910.032*
C111.1586 (3)0.7546 (3)0.78654 (19)0.0267 (6)
H111.20980.82350.82880.032*
C121.0330 (3)0.7762 (3)0.69497 (19)0.0216 (5)
H120.99790.85950.67490.026*
C130.7256 (2)0.5533 (2)0.45680 (17)0.0156 (5)
C140.7489 (2)0.4999 (2)0.39474 (17)0.0163 (5)
H140.8020.54510.38090.02*
C150.6959 (2)0.3825 (2)0.35318 (17)0.0168 (5)
H150.71160.34950.31020.02*
C160.6189 (2)0.3111 (2)0.37367 (17)0.0167 (5)
C170.5955 (2)0.3657 (2)0.43629 (17)0.0179 (5)
H170.54430.32020.45170.022*
C180.6462 (2)0.4845 (2)0.47526 (17)0.0168 (5)
H180.62670.52010.51550.02*
C190.6003 (3)0.1393 (3)0.2728 (2)0.0234 (5)
H19A0.56720.19570.21820.035*
H19B0.55360.05750.24820.035*
H19C0.70130.12780.31130.035*
C200.5016 (3)0.1166 (3)0.3625 (2)0.0278 (6)
H20A0.56680.10170.43260.042*
H20B0.47430.03590.32820.042*
H20C0.41840.15990.34630.042*
U11U22U33U12U13U23
Se10.02080 (14)0.02423 (15)0.02604 (15)0.00213 (10)0.01530 (12)−0.00154 (11)
P10.0118 (3)0.0177 (3)0.0128 (3)−0.0002 (2)0.0066 (2)0.0010 (2)
N10.0205 (10)0.0189 (11)0.0198 (11)−0.0039 (8)0.0116 (9)−0.0033 (8)
C10.0143 (11)0.0166 (11)0.0149 (11)0.0002 (9)0.0081 (9)−0.0001 (9)
C20.0152 (12)0.0482 (18)0.0205 (13)0.0057 (12)0.0103 (11)0.0125 (12)
C30.0191 (13)0.060 (2)0.0305 (16)0.0037 (14)0.0173 (13)0.0129 (15)
C40.0248 (13)0.0277 (14)0.0226 (13)0.0009 (11)0.0168 (12)0.0028 (11)
C50.0216 (12)0.0262 (13)0.0161 (12)0.0016 (10)0.0102 (11)0.0051 (10)
C60.0138 (11)0.0274 (13)0.0186 (12)−0.0003 (10)0.0082 (10)0.0033 (10)
C70.0135 (10)0.0210 (12)0.0130 (11)−0.0011 (9)0.0078 (9)0.0007 (9)
C80.0152 (11)0.0237 (12)0.0154 (11)0.0014 (9)0.0098 (10)0.0027 (9)
C90.0179 (12)0.0332 (15)0.0192 (13)0.0073 (10)0.0122 (11)0.0094 (11)
C100.0144 (12)0.0492 (18)0.0126 (12)0.0013 (11)0.0065 (10)0.0035 (11)
C110.0200 (13)0.0401 (17)0.0159 (12)−0.0093 (12)0.0091 (11)−0.0090 (11)
C120.0202 (12)0.0248 (13)0.0196 (13)−0.0038 (10)0.0121 (11)−0.0028 (10)
C130.0096 (10)0.0197 (11)0.0124 (11)0.0007 (9)0.0043 (9)0.0013 (9)
C140.0122 (10)0.0192 (12)0.0144 (11)0.0005 (9)0.0067 (9)0.0010 (9)
C150.0138 (11)0.0206 (12)0.0142 (11)0.0019 (9)0.0077 (9)−0.0003 (9)
C160.0114 (10)0.0183 (11)0.0126 (11)0.0007 (9)0.0035 (9)0.0004 (9)
C170.0149 (11)0.0221 (12)0.0149 (11)−0.0033 (9)0.0082 (10)0.0004 (9)
C180.0142 (11)0.0223 (12)0.0119 (11)−0.0003 (9)0.0071 (9)0.0007 (9)
C190.0197 (12)0.0226 (13)0.0239 (13)−0.0016 (10)0.0114 (11)−0.0058 (10)
C200.0345 (15)0.0219 (13)0.0248 (14)−0.0096 (11)0.0172 (13)−0.0030 (11)
Se1—P12.1069 (7)C9—H90.95
P1—C131.800 (3)C10—C111.388 (4)
P1—C11.818 (3)C10—H100.95
P1—C71.823 (2)C11—C121.392 (4)
N1—C161.369 (3)C11—H110.95
N1—C201.452 (3)C12—H120.95
N1—C191.461 (3)C13—C181.399 (3)
C1—C61.392 (3)C13—C141.402 (3)
C1—C21.394 (3)C14—C151.386 (3)
C2—C31.391 (4)C14—H140.95
C2—H20.95C15—C161.414 (3)
C3—C41.380 (4)C15—H150.95
C3—H30.95C16—C171.417 (4)
C4—C51.390 (4)C17—C181.385 (3)
C4—H40.95C17—H170.95
C5—C61.390 (4)C18—H180.95
C5—H50.95C19—H19A0.98
C6—H60.95C19—H19B0.98
C7—C81.394 (3)C19—H19C0.98
C7—C121.406 (4)C20—H20A0.98
C8—C91.404 (3)C20—H20B0.98
C8—H80.95C20—H20C0.98
C9—C101.383 (4)
C13—P1—C1104.77 (11)C11—C10—H10119.7
C13—P1—C7106.04 (11)C10—C11—C12120.4 (3)
C1—P1—C7105.02 (11)C10—C11—H11119.8
C13—P1—Se1112.98 (8)C12—C11—H11119.8
C1—P1—Se1113.96 (8)C11—C12—C7119.5 (3)
C7—P1—Se1113.26 (8)C11—C12—H12120.2
C16—N1—C20120.4 (2)C7—C12—H12120.2
C16—N1—C19119.9 (2)C18—C13—C14117.8 (2)
C20—N1—C19119.0 (2)C18—C13—P1120.45 (19)
C6—C1—C2119.2 (2)C14—C13—P1121.71 (18)
C6—C1—P1118.79 (18)C15—C14—C13121.4 (2)
C2—C1—P1121.80 (19)C15—C14—H14119.3
C3—C2—C1120.2 (3)C13—C14—H14119.3
C3—C2—H2119.9C14—C15—C16121.0 (2)
C1—C2—H2119.9C14—C15—H15119.5
C4—C3—C2120.5 (3)C16—C15—H15119.5
C4—C3—H3119.8N1—C16—C15120.9 (2)
C2—C3—H3119.8N1—C16—C17121.7 (2)
C3—C4—C5119.5 (3)C15—C16—C17117.3 (2)
C3—C4—H4120.2C18—C17—C16120.8 (2)
C5—C4—H4120.2C18—C17—H17119.6
C6—C5—C4120.4 (2)C16—C17—H17119.6
C6—C5—H5119.8C17—C18—C13121.6 (2)
C4—C5—H5119.8C17—C18—H18119.2
C5—C6—C1120.2 (2)C13—C18—H18119.2
C5—C6—H6119.9N1—C19—H19A109.5
C1—C6—H6119.9N1—C19—H19B109.5
C8—C7—C12119.8 (2)H19A—C19—H19B109.5
C8—C7—P1121.55 (19)N1—C19—H19C109.5
C12—C7—P1118.67 (19)H19A—C19—H19C109.5
C7—C8—C9120.0 (2)H19B—C19—H19C109.5
C7—C8—H8120N1—C20—H20A109.5
C9—C8—H8120N1—C20—H20B109.5
C10—C9—C8119.7 (3)H20A—C20—H20B109.5
C10—C9—H9120.1N1—C20—H20C109.5
C8—C9—H9120.1H20A—C20—H20C109.5
C9—C10—C11120.6 (2)H20B—C20—H20C109.5
C9—C10—H10119.7
C13—P1—C1—C674.9 (2)C9—C10—C11—C120.1 (4)
C7—P1—C1—C6−173.6 (2)C10—C11—C12—C7−0.6 (4)
Se1—P1—C1—C6−49.0 (2)C8—C7—C12—C110.4 (4)
C13—P1—C1—C2−99.9 (2)P1—C7—C12—C11−179.1 (2)
C7—P1—C1—C211.6 (3)C1—P1—C13—C18−165.27 (19)
Se1—P1—C1—C2136.2 (2)C7—P1—C13—C1884.0 (2)
C6—C1—C2—C3−0.5 (5)Se1—P1—C13—C18−40.7 (2)
P1—C1—C2—C3174.3 (3)C1—P1—C13—C1415.1 (2)
C1—C2—C3—C4−0.3 (5)C7—P1—C13—C14−95.7 (2)
C2—C3—C4—C50.1 (5)Se1—P1—C13—C14139.70 (18)
C3—C4—C5—C60.9 (4)C18—C13—C14—C15−0.3 (3)
C4—C5—C6—C1−1.7 (4)P1—C13—C14—C15179.32 (18)
C2—C1—C6—C51.4 (4)C13—C14—C15—C16−1.4 (4)
P1—C1—C6—C5−173.5 (2)C20—N1—C16—C15173.9 (2)
C13—P1—C7—C83.9 (2)C19—N1—C16—C153.2 (3)
C1—P1—C7—C8−106.7 (2)C20—N1—C16—C17−6.6 (4)
Se1—P1—C7—C8128.35 (19)C19—N1—C16—C17−177.3 (2)
C13—P1—C7—C12−176.58 (19)C14—C15—C16—N1−179.0 (2)
C1—P1—C7—C1272.8 (2)C14—C15—C16—C171.5 (3)
Se1—P1—C7—C12−52.1 (2)N1—C16—C17—C18−179.4 (2)
C12—C7—C8—C90.4 (4)C15—C16—C17—C180.1 (3)
P1—C7—C8—C9179.88 (19)C16—C17—C18—C13−1.9 (4)
C7—C8—C9—C10−0.9 (4)C14—C13—C18—C172.0 (3)
C8—C9—C10—C110.7 (4)P1—C13—C18—C17−177.68 (18)
D—H···AD—HH···AD···AD—H···A
C20—H20A···Se1i0.983.253.833 (3)120
C20—H20C···Se1ii0.983.073.707 (3)124
C4—H4···Cg1iii0.952.663.476 (4)145
C15—H15···Cg1iv0.952.903.699 (3)142
C19—H19B···Cg2v0.982.793.627 (3)144
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 refer to the centroids of the C7–C12 and C13–C18 rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C20—H20A⋯Se1i 0.983.253.833 (3)120
C20—H20C⋯Se1ii 0.983.073.707 (3)124
C4—H4⋯Cg1iii 0.952.663.476 (4)145
C15—H15⋯Cg1iv 0.952.903.699 (3)142
C19—H19B⋯Cg2v 0.982.793.627 (3)144

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

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

Authors:  Frank H Allen
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Journal:  Acta Crystallogr C       Date:  2001-07-09       Impact factor: 1.172

3.  A short history of SHELX.

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

4.  Conformational variability of molecules in different crystal environments: a database study.

Authors:  Ze F Weng; W D Sam Motherwell; Frank H Allen; Jacqueline M Cole
Journal:  Acta Crystallogr B       Date:  2008-05-15

5.  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

6.  Dicyclo-hex-yl[4-(dimethyl-amino)-phen-yl]phosphine selenide.

Authors:  Zanele H Phasha; Sizwe Makhoba; Alfred Muller
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-23
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