Acetonyltriphenyl­phospho­nium nitrate

Diop, T.; Diop, L.; Kučeráková, M.; Dušek, M.

doi:10.1107/S1600536813002110

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 (C-C) = 0.002 Å
R = 0.033
wR = 0.094
Data-to-parameter ratio = 13.6
Details

Acetonyltriphenylphosphonium nitrate

Tidiane Diop,^a ^* Libasse Diop,^a Monika Kuceráková ^b and Michal Dusek ^b

^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-HO hydrogen bonds help to consolidate the crystal packing.

Related literature

For crystal structures containing triphenylphosphonium moieties, see: van der Sluis & Spek (1990); Boys et al. (1995); Zhang et al. (2004); Evans (2010); Kavitha et al. (2012).

Experimental

Crystal data

C₂₁H₂₀OP⁺·NO₃^-
M_r = 381.4
Monoclinic, C 2/c
a = 14.0928 (5) Å
b = 12.6455 (3) Å
c = 21.2684 (6) Å
= 90.667 (2)°
V = 3790.00 (19) Å³
Z = 8
Cu K radiation
= 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) T_min = 0.271, T_max = 1
22035 measured reflections
3389 independent reflections
2969 reflections with I > 3(I)
R_int = 0.040

Refinement

R[F² > 3(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
_max = 0.27 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H1c5O3ⁱ	0.960 (13)	2.252 (13)	3.2053 (18)	172.1 (12)
C5-H3c5O2ⁱⁱ	0.960 (13)	2.403 (12)	3.1936 (18)	139.4 (11)
C7-H1c7O3ⁱ	0.96	2.49	3.4365 (19)	167.90
C8-H1c8O3	0.96	2.50	3.177 (2)	127.75
C10-H1c10O2ⁱⁱ	0.96	2.49	3.3706 (19)	152.50
C15-H1c15O1	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); 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.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Evans, C. (2010). Acta Cryst. E66, o384-o385.
Kavitha, C. N., Yathirajan, H. S., Dayananda, A. S., Gerber, T., Hosten, E. & Betz, R. (2012). Acta Cryst. E68, o3115.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.
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.
Zhang, X., Zhong, P., Hu, M., Lin, D. & Lin, J. (2004). Acta Cryst. E60, o1200-o1201.

organic compounds