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Volume 69 
Part 2 
Page o303  
February 2013  

Received 9 December 2012
Accepted 21 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.094
Data-to-parameter ratio = 13.6
Details
Open access

Acetonyltriphenylphosphonium nitrate

aLaboratoire de Chimie Minerale et Analytique, Departement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: tijchimia@yahoo.fr

Crystals of the title salt, C21H20OP+·NO3-, are composed of acetonyltriphenylphosphonium cations and nitrate anions that mainly interact through electrostatic forces. The P atom in the cation has a slightly distorted tetrahedral environment, with C-P-C angles ranging from 104.79 (7) to 112.59 (6)°. The sum of O-N-O angles of the nitrate anion is 359.99°, reflecting its trigonal-planar character. C-H...O hydrogen bonds help to consolidate the crystal packing.

Related literature

For crystal structures containing triphenylphosphonium moieties, see: van der Sluis & Spek (1990[Sluis, P. van der & Spek, A. L. (1990). Acta Cryst. C46, 2429-2431.]); Boys et al. (1995[Boys, D., Araya-Maturana, R., González, O. & Manríquez, V. (1995). Acta Cryst. C51, 105-107.]); Zhang et al. (2004[Zhang, X., Zhong, P., Hu, M., Lin, D. & Lin, J. (2004). Acta Cryst. E60, o1200-o1201.]); Evans (2010[Evans, C. (2010). Acta Cryst. E66, o384-o385.]); Kavitha et al. (2012[Kavitha, C. N., Yathirajan, H. S., Dayananda, A. S., Gerber, T., Hosten, E. & Betz, R. (2012). Acta Cryst. E68, o3115.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20OP+·NO3-

  • Mr = 381.4

  • Monoclinic, C 2/c

  • a = 14.0928 (5) Å

  • b = 12.6455 (3) Å

  • c = 21.2684 (6) Å

  • [beta] = 90.667 (2)°

  • V = 3790.00 (19) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 1.51 mm-1

  • T = 120 K

  • 0.19 × 0.18 × 0.12 mm

Data collection
  • Agilent Xcalibur diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.] Tmin = 0.271, Tmax = 1

  • 22035 measured reflections

  • 3389 independent reflections

  • 2969 reflections with I > 3[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 3[sigma](F2)] = 0.033

  • wR(F2) = 0.094

  • S = 1.63

  • 3389 reflections

  • 250 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H1c5...O3i 0.960 (13) 2.252 (13) 3.2053 (18) 172.1 (12)
C5-H3c5...O2ii 0.960 (13) 2.403 (12) 3.1936 (18) 139.4 (11)
C7-H1c7...O3i 0.96 2.49 3.4365 (19) 167.90
C8-H1c8...O3 0.96 2.50 3.177 (2) 127.75
C10-H1c10...O2ii 0.96 2.49 3.3706 (19) 152.50
C15-H1c15...O1 0.96 2.36 3.1780 (19) 142.99
Symmetry codes: (i) [-x+1, y, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: JANA2006.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2713 ).


Acknowledgements

We acknowledge the Praemium Academiae project of the Academy of Sciences of the Czech Republic.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Boys, D., Araya-Maturana, R., González, O. & Manríquez, V. (1995). Acta Cryst. C51, 105-107.  [CrossRef] [details]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Evans, C. (2010). Acta Cryst. E66, o384-o385.  [CrossRef] [details]
Kavitha, C. N., Yathirajan, H. S., Dayananda, A. S., Gerber, T., Hosten, E. & Betz, R. (2012). Acta Cryst. E68, o3115.  [CrossRef] [details]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic.
Sluis, P. van der & Spek, A. L. (1990). Acta Cryst. C46, 2429-2431.  [CrossRef] [details]
Zhang, X., Zhong, P., Hu, M., Lin, D. & Lin, J. (2004). Acta Cryst. E60, o1200-o1201.  [CrossRef] [details]


Acta Cryst (2013). E69, o303  [ doi:10.1107/S1600536813002110 ]

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