Literature DB >> 24765055

Diphen-yl[(phenyl-sulfan-yl)meth-yl]-λ(5)-phosphane-thione.

Abstract

The title compound, C19H17PS2, results from the direct deprotonation of di-phenyl-methyl-phosphine sulfide and subsequent reaction with pan class="Chemical">diphenyl di-sulfide. The C-P and C-S bond lengths of 1.8242 (18) and 1.8009 (18) Å, respectively, of the central P-C-S linkage are comparable to those found in the sulfonyl analogue, but are considerably longer than those reported for the dimetallated sulfonyl compound. The dihedral angle between the benzene rings of the di-phenyl-methyl moiety is 69.46 (7)°. No distinct inter-molecular inter-actions are present in the crystal structure.

Entities: Chemical Disease Gene

Year: 2014 PMID： 24765055 PMCID： PMC3998441 DOI： 10.1107/S1600536814004292

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

Related literature

For the sulfonyl and dimetallated sulfonyl analogues, see: Schröter & Gessner (2012 ▶). For background to precursors for dilithio methandiides and their carbene complexes, see: Becker & Gessner (2014a ▶,b ▶); Cantat et al. (2006 ▶, 2008 ▶); Cavell et al. (2001 ▶); Cooper et al. (2010 ▶); Gessner (2012 ▶); Gessner et al. (2013 ▶); Harder (2011 ▶); Kasani et al. (1999 ▶); Liddle et al. (2011 ▶); Ong et al. (1999 ▶).

Experimental

Crystal data

C19H17PS2 M = 340.42 Monoclinic, a = 9.3748 (13) Å b = 18.598 (3) Å c = 10.0941 (14) Å β = 101.044 (2)° V = 1727.3 (4) Å3 Z = 4 Mo Kα radiation μ = 0.39 mm−1 T = 173 K 0.38 × 0.18 × 0.15 mm

Data collection

Bruker APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.953, T max = 0.979 10734 measured reflections 3033 independent reflections 2663 reflections with I > 2σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.091 S = 1.05 3033 reflections 199 parameters H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.23 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-pan class="Chemical">Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814004292/wm5008sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004292/wm5008Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814004292/wm5008Isup3.cml CCDC reference: 988671 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₉H₁₇PS₂	F(000) = 712
M_r = 340.42	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4352 reflections
a = 9.3748 (13) Å	θ = 2.2–25°
b = 18.598 (3) Å	µ = 0.39 mm⁻¹
c = 10.0941 (14) Å	T = 173 K
β = 101.044 (2)°	Block, colourless
V = 1727.3 (4) Å³	0.38 × 0.18 × 0.15 mm
Z = 4

Bruker APEX CCD diffractometer	3033 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω–scans	θ_max = 25°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −11→7
T_min = 0.953, T_max = 0.979	k = −22→22
10734 measured reflections	l = −12→11

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0403P)² + 0.5374P] where P = (F_o² + 2F_c²)/3
3033 reflections	(Δ/σ)_max = 0.007
199 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³
0 constraints

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.

	x	y	z	U_iso*/U_eq
C1	0.52214 (19)	0.08028 (9)	0.30067 (17)	0.0288 (4)
C2	0.5712 (2)	0.02245 (10)	0.23596 (19)	0.0380 (4)
H2	0.535	0.0147	0.1425	0.046*
C3	0.6729 (2)	−0.02428 (11)	0.3069 (2)	0.0472 (5)
H3	0.7053	−0.0643	0.2623	0.057*
C4	0.7274 (2)	−0.01291 (10)	0.4421 (2)	0.0413 (5)
H4	0.7987	−0.0445	0.49	0.05*
C5	0.6782 (2)	0.04426 (10)	0.50795 (19)	0.0397 (5)
H5	0.7153	0.0518	0.6013	0.048*
C6	0.5750 (2)	0.09060 (10)	0.43818 (18)	0.0356 (4)
H6	0.5401	0.1295	0.484	0.043*
C7	0.2351 (2)	0.14772 (9)	0.28387 (18)	0.0311 (4)
C8	0.1148 (2)	0.10634 (12)	0.2316 (2)	0.0463 (5)
H8	0.1162	0.0763	0.1558	0.056*
C9	−0.0079 (2)	0.10857 (13)	0.2896 (2)	0.0551 (6)
H9	−0.0897	0.0796	0.2539	0.066*
C10	−0.0118 (2)	0.15236 (13)	0.3978 (2)	0.0510 (6)
H10	−0.0961	0.1538	0.4372	0.061*
C11	0.1064 (2)	0.19424 (11)	0.4494 (2)	0.0487 (5)
H11	0.1031	0.225	0.5239	0.058*
C12	0.2297 (2)	0.19198 (10)	0.3942 (2)	0.0402 (5)
H12	0.3114	0.2207	0.4314	0.048*
C13	0.4787 (2)	0.23097 (9)	0.24179 (18)	0.0322 (4)
H13A	0.4074	0.2696	0.2109	0.039*
H13B	0.5143	0.2366	0.3401	0.039*
C14	0.7380 (2)	0.30474 (9)	0.24404 (18)	0.0332 (4)
C15	0.8792 (2)	0.30812 (11)	0.2215 (2)	0.0467 (5)
H15	0.9118	0.2738	0.1642	0.056*
C16	0.9721 (2)	0.36083 (13)	0.2815 (3)	0.0568 (6)
H16	1.0679	0.3635	0.264	0.068*
C17	0.9273 (3)	0.40970 (13)	0.3668 (2)	0.0573 (6)
H17	0.9923	0.4458	0.4087	0.069*
C18	0.7882 (3)	0.40641 (12)	0.3914 (2)	0.0534 (6)
H18	0.7574	0.4402	0.4505	0.064*
C19	0.6925 (2)	0.35395 (11)	0.3302 (2)	0.0432 (5)
H19	0.5964	0.3518	0.3473	0.052*
P1	0.39369 (5)	0.14308 (2)	0.20578 (4)	0.02841 (14)
S1	0.34680 (6)	0.12132 (3)	0.01308 (5)	0.03941 (16)
S2	0.62814 (5)	0.23650 (3)	0.15364 (5)	0.03730 (15)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0287 (9)	0.0300 (9)	0.0276 (9)	−0.0035 (7)	0.0050 (7)	0.0025 (7)
C2	0.0430 (12)	0.0405 (10)	0.0295 (9)	0.0046 (9)	0.0047 (9)	−0.0024 (8)
C3	0.0533 (13)	0.0452 (11)	0.0428 (12)	0.0134 (10)	0.0090 (10)	−0.0047 (9)
C4	0.0389 (11)	0.0410 (11)	0.0422 (11)	0.0053 (9)	0.0031 (9)	0.0097 (9)
C5	0.0447 (12)	0.0409 (11)	0.0300 (10)	−0.0054 (9)	−0.0017 (9)	0.0033 (8)
C6	0.0440 (12)	0.0315 (9)	0.0303 (9)	−0.0023 (8)	0.0044 (9)	−0.0036 (7)
C7	0.0284 (10)	0.0311 (9)	0.0327 (9)	−0.0017 (7)	0.0035 (8)	0.0038 (7)
C8	0.0412 (12)	0.0577 (13)	0.0393 (11)	−0.0143 (10)	0.0055 (10)	−0.0050 (9)
C9	0.0346 (12)	0.0731 (16)	0.0558 (14)	−0.0193 (11)	0.0038 (11)	0.0046 (12)
C10	0.0346 (12)	0.0627 (14)	0.0595 (14)	0.0025 (10)	0.0187 (11)	0.0135 (11)
C11	0.0469 (13)	0.0447 (11)	0.0607 (13)	0.0000 (10)	0.0259 (11)	−0.0029 (10)
C12	0.0376 (11)	0.0376 (10)	0.0485 (11)	−0.0076 (9)	0.0158 (9)	−0.0062 (9)
C13	0.0333 (10)	0.0323 (9)	0.0326 (9)	−0.0035 (7)	0.0102 (8)	0.0012 (7)
C14	0.0336 (10)	0.0336 (9)	0.0322 (9)	−0.0029 (8)	0.0054 (8)	0.0091 (7)
C15	0.0374 (12)	0.0456 (12)	0.0589 (13)	−0.0007 (9)	0.0140 (10)	0.0068 (10)
C16	0.0345 (12)	0.0594 (14)	0.0737 (16)	−0.0078 (10)	0.0032 (12)	0.0103 (12)
C17	0.0520 (15)	0.0561 (14)	0.0552 (14)	−0.0188 (11)	−0.0111 (12)	0.0049 (11)
C18	0.0675 (16)	0.0501 (13)	0.0414 (12)	−0.0115 (11)	0.0075 (11)	−0.0078 (10)
C19	0.0445 (12)	0.0440 (11)	0.0430 (11)	−0.0064 (9)	0.0132 (10)	−0.0019 (9)
P1	0.0297 (3)	0.0295 (2)	0.0257 (2)	−0.00220 (18)	0.0045 (2)	−0.00026 (17)
S1	0.0459 (3)	0.0451 (3)	0.0251 (3)	0.0004 (2)	0.0013 (2)	−0.00118 (19)
S2	0.0409 (3)	0.0377 (3)	0.0369 (3)	−0.0078 (2)	0.0167 (2)	−0.00314 (19)

C1—C2	1.382 (3)	C11—C12	1.377 (3)
C1—C6	1.395 (2)	C11—H11	0.95
C1—P1	1.8138 (18)	C12—H12	0.95
C2—C3	1.384 (3)	C13—S2	1.8009 (18)
C2—H2	0.95	C13—P1	1.8242 (18)
C3—C4	1.379 (3)	C13—H13A	0.99
C3—H3	0.95	C13—H13B	0.99
C4—C5	1.379 (3)	C14—C19	1.385 (3)
C4—H4	0.95	C14—C15	1.387 (3)
C5—C6	1.384 (3)	C14—S2	1.7729 (19)
C5—H5	0.95	C15—C16	1.373 (3)
C6—H6	0.95	C15—H15	0.95
C7—C8	1.384 (3)	C16—C17	1.371 (3)
C7—C12	1.393 (3)	C16—H16	0.95
C7—P1	1.8137 (18)	C17—C18	1.375 (3)
C8—C9	1.388 (3)	C17—H17	0.95
C8—H8	0.95	C18—C19	1.387 (3)
C9—C10	1.369 (3)	C18—H18	0.95
C9—H9	0.95	C19—H19	0.95
C10—C11	1.373 (3)	P1—S1	1.9527 (7)
C10—H10	0.95

C2—C1—C6	119.37 (17)	C11—C12—H12	119.9
C2—C1—P1	119.93 (14)	C7—C12—H12	119.9
C6—C1—P1	120.68 (13)	S2—C13—P1	107.72 (9)
C1—C2—C3	120.18 (17)	S2—C13—H13A	110.2
C1—C2—H2	119.9	P1—C13—H13A	110.2
C3—C2—H2	119.9	S2—C13—H13B	110.2
C4—C3—C2	120.23 (19)	P1—C13—H13B	110.2
C4—C3—H3	119.9	H13A—C13—H13B	108.5
C2—C3—H3	119.9	C19—C14—C15	119.44 (18)
C5—C4—C3	120.05 (18)	C19—C14—S2	125.31 (15)
C5—C4—H4	120	C15—C14—S2	115.23 (15)
C3—C4—H4	120	C16—C15—C14	120.3 (2)
C4—C5—C6	120.05 (17)	C16—C15—H15	119.9
C4—C5—H5	120	C14—C15—H15	119.9
C6—C5—H5	120	C17—C16—C15	120.4 (2)
C5—C6—C1	120.09 (17)	C17—C16—H16	119.8
C5—C6—H6	120	C15—C16—H16	119.8
C1—C6—H6	120	C16—C17—C18	119.9 (2)
C8—C7—C12	118.81 (18)	C16—C17—H17	120
C8—C7—P1	118.95 (15)	C18—C17—H17	120
C12—C7—P1	122.23 (14)	C17—C18—C19	120.4 (2)
C7—C8—C9	120.2 (2)	C17—C18—H18	119.8
C7—C8—H8	119.9	C19—C18—H18	119.8
C9—C8—H8	119.9	C14—C19—C18	119.6 (2)
C10—C9—C8	120.3 (2)	C14—C19—H19	120.2
C10—C9—H9	119.8	C18—C19—H19	120.2
C8—C9—H9	119.8	C7—P1—C1	108.53 (8)
C9—C10—C11	119.9 (2)	C7—P1—C13	103.53 (8)
C9—C10—H10	120.1	C1—P1—C13	104.55 (8)
C11—C10—H10	120.1	C7—P1—S1	113.32 (6)
C10—C11—C12	120.5 (2)	C1—P1—S1	113.12 (6)
C10—C11—H11	119.7	C13—P1—S1	112.99 (6)
C12—C11—H11	119.7	C14—S2—C13	102.51 (9)
C11—C12—C7	120.20 (19)

8 in total

1. A monomeric dilithio methandiide with a distorted trans-planar four-coordinate carbon.

Authors: Oliver J Cooper; Ashley J Wooles; Jonathan McMaster; William Lewis; Alexander J Blake; Stephen T Liddle
Journal: Angew Chem Int Ed Engl Date: 2010-07-26 Impact factor: 15.336

2. A short history of SHELX.

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

3. Tetrahedral versus planar four-coordinate carbon: a sulfonyl-substituted methandiide.

Authors: Peter Schröter; Viktoria H Gessner
Journal: Chemistry Date: 2012-07-26 Impact factor: 5.236

4. Synthesis and bonding in carbene complexes of an unsymmetrical dilithio methandiide: a combined experimental and theoretical study.

Authors: Viktoria H Gessner; Florian Meier; Diana Uhrich; Martin Kaupp
Journal: Chemistry Date: 2013-10-21 Impact factor: 5.236