[Journal logo]

Volume 68 
Part 1 
Pages o47-o48  
January 2012  

Received 16 November 2011
Accepted 30 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](N-C) = 0.003 Å
R = 0.030
wR = 0.068
Data-to-parameter ratio = 13.5
Details
Open access

Tris(2-carbamoylguanidinium) hydrogen fluorophosphonate fluorophosphonate monohydrate

aInstitute of Physics of the Czech Academy of Sciences, v. v. i., Na Slovance 2, 182 21 Praha 8, Czech Republic, and bDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 12843 Prague 2, Czech Republic
Correspondence e-mail: fabry@fzu.cz

The title structure, 3C2H7N4O+·HFPO3-·FPO32-·H2O, contains three independent 2-carbamoylguanidinium cations, one fluorophosphonate, one hydrogen fluorophosphonate and one water molecule. There are three different layers in the structure that are nearly perpendicular to the c axis. Each layer contains a cation and the layers differ by the respective presence of the water molecule, the hydrogen fluorophosphonate and fluorophosphonate anions. N-H...O hydrogen bonds between the guanylurea molecules that interconnect the molecules within each layer are strong. The layers are interconnected by strong and weak O-H...O hydrogen bonds between the anions and water molecules, respectively. Interestingly, the configuration of the layers is quite similar to that observed in 2-carbamoylguanidinium hydrogen fluorophosphonate [Fábry et al. (2012). Acta Cryst. C68, o76-o83]. There is also present a N-H...F hydrogen bond in the structure which occurs quite rarely.

Related literature

For the related structures 2-carbamoylguanidinium hydrogen fluorophosphonate and bis[guanylurea)(1+)] fluorophosphonate dihydrate, see: Fábry et al. (2012a[Fábry, J., Fridrichová, M., Dusek, M., Fejfarová, K. & Krupková, R. (2012a). Acta Cryst. C68, o76-o83.],b[Fábry, J., Fridrichová, M., Dusek, M., Fejfarová, K. & Krupková, R. (2012b). Acta Cryst. C68, o71-o75.]). For the related compound 2-carbamoylguanidinium hydrogen phosphite and its physical properties, see: Fridrichová et al. (2010a[Fridrichová, M., Nemec, I., Císarová, I. & Chvostová, D. (2010b). Phase Trans. 83, 761-767.],b[Fridrichová, M., Nemec, I., Císarová, I. & Nemec, P. (2010a). CrystEngComm, 12, 2054-2056.]); Kroupa & Fridrichová (2011[Kroupa, J. & Fridrichová, M. (2011). J. Opt. 13, 035204 (7 pp.)]). For the applied values of the constraints for water molecules, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For preparation of the precursors, see Ostrogovich (1911[Ostrogovich, A. (1911). Gazz. Chim. Ital. 39, 540-549.]); Schülke & Kayser (1991[Schülke, U. & Kayser, R. (1991). Z. Anorg. Allg. Chem. 600, 221-226.]); Scoponi (1991[Scoponi, M., Polo, E., Bertolasi, V., Carassiti, V. & Bertelli, G. (1991). J. Chem. Soc. Perkin Trans. 2, pp. 1619-1624.]). For the involvement of fluorine in hydrogen bonds, see: Dunitz & Taylor (1997[Dunitz, J. D. & Taylor, R. (1997). Chem. Eur. J. 3, 89-98.]); Krupková et al. (2002[Krupková, R., Fábry, J., Císarová, I. & Vanek, P. (2002). Acta Cryst. C58, i66-i68.]). For the denomination of the hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, p. 13. New York: Oxford University Press Inc.]). For the extinction correction, see: Becker & Coppens (1974[Becker, P. J. & Coppens, P. (1974). Acta Cryst. A30, 129-147.]).

[Scheme 1]

Experimental

Crystal data
  • 3C2H7N4O+·HFO3P-·FO3P2-·H2O

  • Mr = 524.3

  • Triclinic, P 1

  • a = 6.7523 (3) Å

  • b = 8.2926 (3) Å

  • c = 9.7297 (4) Å

  • [alpha] = 100.630 (3)°

  • [beta] = 90.885 (3)°

  • [gamma] = 99.168 (3)°

  • V = 528.05 (4) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 297 K

  • 0.60 × 0.45 × 0.40 mm

Data collection
  • Oxford Diffraction Xcalibur Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO, Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.852, Tmax = 0.888

  • 8499 measured reflections

  • 4769 independent reflections

  • 4203 reflections with I > 3[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.068

  • S = 1.52

  • 4769 reflections

  • 352 parameters

  • 22 restraints

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983)[Flack, H. D. (1983). Acta Cryst. A39, 876-881.], 2216 Friedel pairs

  • Flack parameter: 0.08 (6)

Table 1
The hydrogen-bond (Å, °) pattern in the title structure

Atoms N1-N4, N5-N8 and N9-N12 are situated in the first, second and third layers, respectively. The atoms in the blocks comprise the corresponding atoms in the respective layers: e.g. N2-H2n2...O1, N5-H2n5...O2, N10-H1n10...O3.

D-H...A D-H H...A D...A D-H...A
O11-H1o11...O21 0.80 (3) 1.72 (4) 2.515 (3) 174 (4)
Ow-H1ow...O13 0.82 (2) 1.957 (19) 2.754 (3) 164 (2)
Ow-H2ow...O22i 0.82 (2) 2.253 (17) 3.037 (3) 160 (3)
Ow-H2ow...O23i 0.82 (2) 2.41 (3) 3.023 (3) 132 (3)
         
N1-H1n1...Ow 0.860 (18) 2.302 (15) 3.022 (4) 141 (2)
N1-H2n1...O1ii 0.861 (17) 2.24 (2) 2.795 (3) 122.4 (15)
N1-H2n1...O23iii 0.861 (15) 2.431 (14) 3.141 (3) 140.3 (18)
N6-H2n6...O2ii 0.860 (17) 2.23 (2) 2.750 (3) 119.0 (15)
N6-H2n6...O12iv 0.860 (17) 2.491 (15) 3.200 (3) 140.3 (17)
N6-H1n6...O11 0.861 (19) 2.28 (2) 3.141 (3) 174 (2)
N9-H2n9...O21iv 0.860 (17) 2.08 (2) 2.916 (2) 164 (2)
N9-H1n9...F2v 0.860 (7) 2.479 (19) 3.096 (2) 129 (2)
N9-H1n9...O3 0.860 (7) 2.01 (2) 2.634 (2) 129 (2)
         
N2-H2n2...Ow 0.861 (16) 2.12 (2) 2.894 (3) 150 (2)
N2-H1n2...O1 0.861 (12) 1.94 (2) 2.618 (3) 135 (2)
N5-H2n5...O13 0.862 (19) 2.07 (2) 2.906 (3) 165 (2)
N5-H1n5...O2 0.860 (7) 2.03 (2) 2.646 (3) 128 (2)
N10-H1n10...O21iv 0.860 (13) 2.595 (10) 3.318 (3) 142.5 (17)
N10-H2n10...O3vi 0.861 (13) 2.186 (14) 2.750 (3) 122.9 (11)
N10-H2n10...O22 0.861 (13) 2.524 (13) 3.209 (3) 137.1 (11)
         
N3-H1n3...O23iii 0.89 1.95 2.770 (3) 153
N7-H1n7...O12iv 0.89 1.93 2.807 (3) 166
N11-H1n11...O22 0.89 1.93 2.804 (3) 166
         
N4-H1n4...O23vii 0.860 (14) 2.386 (16) 3.170 (3) 152 (2)
N4-H2n4...Owiv 0.86 (2) 2.32 (2) 3.173 (3) 176 (2)
N8-H2n8...O13iv 0.857 (16) 2.024 (16) 2.877 (3) 173.8 (15)
N8-H1n8...O12viii 0.860 (10) 2.179 (10) 3.034 (3) 173 (3)
N12-H1n12...O21 0.859 (11) 2.115 (16) 2.972 (2) 175 (3)
N12-H2n12...O22ii 0.859 (11) 2.198 (11) 3.031 (3) 163 (3)
Symmetry codes: (i) x, y, z-1; (ii) x-1, y, z; (iii) x, y-1, z-1; (iv) x, y-1, z; (v) x-1, y-1, z; (vi) x+1, y, z; (vii) x+1, y-1, z-1; (viii) x+1, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999)[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]; program(s) used to refine structure: JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Academy of Sciences of the Czech Republic, Praha, Czech Republic.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact, GbR, Bonn, Germany.]) and Origin (OriginLab, 2000[OriginLab (2000). Origin. OriginLab Corporation, Northampton, USA.]); software used to prepare material for publication: JANA2006.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZJ2040 ).


Acknowledgements

The authors gratefully acknowledge support of this work by the Praemium Academiae project of the Academy of Sciences of the Czech Republic and by grant No. 58608 of the Grant Agency of Charles University in Prague, the Czech Science Foundation (grant No. 203/09/0878) and the long term Research Plan of the Ministry of Education of the Czech Republic (No. MSM0021620857).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Becker, P. J. & Coppens, P. (1974). Acta Cryst. A30, 129-147.  [CrossRef] [details]
Brandenburg, K. (2010). DIAMOND. Crystal Impact, GbR, Bonn, Germany.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, p. 13. New York: Oxford University Press Inc.
Dunitz, J. D. & Taylor, R. (1997). Chem. Eur. J. 3, 89-98.  [CrossRef] [ChemPort]
Fábry, J., Fridrichová, M., Dusek, M., Fejfarová, K. & Krupková, R. (2012a). Acta Cryst. C68, o76-o83. [details]
Fábry, J., Fridrichová, M., Dusek, M., Fejfarová, K. & Krupková, R. (2012b). Acta Cryst. C68, o71-o75. [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Fridrichová, M., Nemec, I., Císarová, I. & Chvostová, D. (2010b). Phase Trans. 83, 761-767.
Fridrichová, M., Nemec, I., Císarová, I. & Nemec, P. (2010a). CrystEngComm, 12, 2054-2056.
Kroupa, J. & Fridrichová, M. (2011). J. Opt. 13, 035204 (7 pp.)  [CrossRef]
Krupková, R., Fábry, J., Císarová, I. & Vanek, P. (2002). Acta Cryst. C58, i66-i68.  [CrossRef] [details]
OriginLab (2000). Origin. OriginLab Corporation, Northampton, USA.
Ostrogovich, A. (1911). Gazz. Chim. Ital. 39, 540-549.  [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Academy of Sciences of the Czech Republic, Praha, Czech Republic.
Schülke, U. & Kayser, R. (1991). Z. Anorg. Allg. Chem. 600, 221-226.  [CrossRef]
Scoponi, M., Polo, E., Bertolasi, V., Carassiti, V. & Bertelli, G. (1991). J. Chem. Soc. Perkin Trans. 2, pp. 1619-1624.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o47-o48   [ doi:10.1107/S1600536811051683 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.