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Volume 69 
Part 8 
Page o1364  
August 2013  

Received 8 July 2013
Accepted 24 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.118
Data-to-parameter ratio = 14.0
Details
Open access

2-Diphenylphosphanyl-1-methyl-1H-benzimidazole

aNorth Carolina A&T State University, 1601 E Market St., Department of Chemistry, Greensboro, NC 27411, USA
Correspondence e-mail: zassefa@ncat.edu

In the title compound, C20H18N2P, the P atom is bonded to the two phenyl and imidazole groups, with an average P-C bond length of 1.828 (2) Å. The three C-P-C bond angles have values consistent with a tetrahedral geometry around the P atom with the fourth site occupied by a H atom. Crystal packing is through van der Waals interactions.

Related literature

For the first synthesis of the title compound and related systems, see: Moore & Whitesides (1982[Moore, S. S. & Whitesides, G. M. (1982). J. Org. Chem. 47, 1489-1493.]). For multimode coordination of diphenylphosphine-substituted benzimidazoles featuring ethylene linkers, see: Hahn et al. (2010[Hahn, F. E., Naziruddin, A. R., Hepp, A. & Pape, T. (2010). Organometallics, 29, 5283-5288.]). For amino-group linkers, see: Braunstein et al. (1997[Braunstein, P., Pietsch, J., Chauvin, Y., DeCian, A. & Fischer, J. (1997). J. Organomet. Chem. 529, 387-393.]). For the coordination of the N,P-type ligand (1-benzyl-2-imidazolyl)diphenylphosphine (BzimPh2P) with several metal ions, see: Burini et al. (2000[Burini, A., Fackler, J. P., Galassi, R., Grant, T. A., Omary, M. A., Rawashdeh-Omary, M. A., Pietroni, B. R. & Staples, R. J. (2000). J. Am. Chem. Soc. 122, 11264-11265.]). For silver complexes with the same ligand, see: Bachechi et al. (2001[Bachechi, F., Burini, A., Fontani, M., Galassi, R., Macchioni, A., Pietroni, B. R., Zanello, P. & Zuccaccia, C. (2001). Inorg. Chim. Acta, 323, 45-54.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N2P

  • Mr = 317.33

  • Triclinic, [P \overline 1]

  • a = 9.574 (2) Å

  • b = 9.904 (3) Å

  • c = 10.513 (3) Å

  • [alpha] = 74.215 (7)°

  • [beta] = 67.172 (7)°

  • [gamma] = 70.346 (7)°

  • V = 853.6 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 200 K

  • 0.50 × 0.50 × 0.05 mm

Data collection
  • Bruker SMART X2S diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.924, Tmax = 0.992

  • 8036 measured reflections

  • 2973 independent reflections

  • 2497 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.118

  • S = 1.06

  • 2973 reflections

  • 212 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Data collection: SMART (Bruker, 2008[Bruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: JMol (Hanson, 2010[Hanson, R. M. (2010). J. Appl. Cryst. 43, 1250-1260.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2457 ).


Acknowledgements

Support for this research from National Science Foundation (CHE-0959406) and the NOAA Educational Partnership Program award number NA06OAR4810187 to NCAT State University as well as support from the donors of the Petroleum Research Fund (ACS-PRF) are kindly acknowledged.

References

Bachechi, F., Burini, A., Fontani, M., Galassi, R., Macchioni, A., Pietroni, B. R., Zanello, P. & Zuccaccia, C. (2001). Inorg. Chim. Acta, 323, 45-54.  [CrossRef] [ChemPort]
Braunstein, P., Pietsch, J., Chauvin, Y., DeCian, A. & Fischer, J. (1997). J. Organomet. Chem. 529, 387-393.  [CrossRef] [ChemPort]
Bruker (2008). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burini, A., Fackler, J. P., Galassi, R., Grant, T. A., Omary, M. A., Rawashdeh-Omary, M. A., Pietroni, B. R. & Staples, R. J. (2000). J. Am. Chem. Soc. 122, 11264-11265.  [CrossRef] [ChemPort]
Hahn, F. E., Naziruddin, A. R., Hepp, A. & Pape, T. (2010). Organometallics, 29, 5283-5288.  [CrossRef] [ChemPort]
Hanson, R. M. (2010). J. Appl. Cryst. 43, 1250-1260.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Moore, S. S. & Whitesides, G. M. (1982). J. Org. Chem. 47, 1489-1493.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1364  [ doi:10.1107/S1600536813020588 ]

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