Redetermined structure of diphenyl­phospho­nimidotriphenyl­phospho­rane: location of the hydrogen atoms and analysis of the inter­molecular inter­actions

Betz, R.; Gerber, T.; Hosten, E.; Schalekamp, H.

doi:10.1107/S1600536811011500

Volume 67
Part 5
Pages o1028-o1029
May 2011

Received 25 March 2011
Accepted 28 March 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R = 0.027
wR = 0.076
Data-to-parameter ratio = 14.7
Details

Redetermined structure of diphenylphosphonimidotriphenylphosphorane: location of the hydrogen atoms and analysis of the intermolecular interactions

Richard Betz,^a ^* Thomas Gerber,^a Eric Hosten ^a and Henk Schalekamp ^a

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

The title compound, C₃₀H₂₅NOP₂, is a bulky phosphazene derivative. Its previous crystal structure [Cameron et al. (1979). Acta Cryst. B35, 1373-1377] is confirmed and its H atoms have been located in the present study. The formal P=N double bond is about 0.05 Å shorter than the P-N single bond and the large P=N-P bond angle reflects the steric strain in the molecule. An intramolecular C-HO interaction occurs. In the crystal, short C-HO contacts connect the molecules into chains propagating in [011], which are cross-linked via C-H [pi] interactions, generating a three-dimensional network. Aromatic [pi] - [pi] stacking also occurs [shortest centroid-centroid separation = 3.6012 (11) Å].

Related literature

For the previous structure determination, see: Cameron et al. (1979). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₃₀H₂₅NOP₂
M_r = 477.45
Orthorhombic, P n a 2₁
a = 17.6607 (12) Å
b = 15.1593 (10) Å
c = 8.9192 (6) Å
V = 2387.9 (3) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 200 K
0.88 × 0.42 × 0.31 mm

Data collection

Bruker APEXII CCD diffractometer
12511 measured reflections
4498 independent reflections
4348 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.076
S = 1.11
4498 reflections
307 parameters
1 restraint
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.25 e Å^-3
Absolute structure: Flack (1983), 1332 Friedel pairs
Flack parameter: -0.03 (6)

Table 1
Selected geometric parameters (Å, °)

P1-N1	1.6014 (13)
P2-N1	1.5532 (13)

P2-N1-P1	146.35 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C32-H32O1	0.95	2.34	3.257 (2)	163
C43-H43O1ⁱ	0.95	2.34	3.257 (2)	162
C45-H45Cg1ⁱⁱ	0.95	2.92	3.846 (2)	165
C55-H55Cg2ⁱⁱⁱ	0.95	2.73	3.644 (2)	163
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) $[-x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5826 ).

Acknowledgements

The authors thank Mr Gerhard Schneeberger for helpful discussions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, USA.
Cameron, A. F., Cameron, I. R. & Keat, R. (1979). Acta Cryst. B35, 1373-1377.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds