Tris(2-carbamoylguanidinium) hydrogen fluoro­phospho­nate fluoro­phospho­nate monohydrate

Fábry, J.; Fridrichová, M.; Dušek, M.; Fejfarová, K.; Krupková, R.

doi:10.1107/S1600536811051683

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 (N-C) = 0.003 Å
R = 0.030
wR = 0.068
Data-to-parameter ratio = 13.5
Details

Tris(2-carbamoylguanidinium) hydrogen fluorophosphonate fluorophosphonate monohydrate

Jan Fábry,^a ^* Michaela Fridrichová,^b Michal Dusek,^a Karla Fejfarová ^a and Radmila Krupková ^a

^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^-·FPO₃^2-·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-HO hydrogen bonds between the guanylurea molecules that interconnect the molecules within each layer are strong. The layers are interconnected by strong and weak O-HO 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-HF 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,b). For the related compound 2-carbamoylguanidinium hydrogen phosphite and its physical properties, see: Fridrichová et al. (2010a,b); Kroupa & Fridrichová (2011). For the applied values of the constraints for water molecules, see: Allen (2002). For preparation of the precursors, see Ostrogovich (1911); Schülke & Kayser (1991); Scoponi (1991). For the involvement of fluorine in hydrogen bonds, see: Dunitz & Taylor (1997); Krupková et al. (2002). For the denomination of the hydrogen bonds, see: Desiraju & Steiner (1999). For the extinction correction, see: Becker & Coppens (1974).

Experimental

Crystal data

3C₂H₇N₄O⁺·HFO₃P^-·FO₃P^2-·H₂O
M_r = 524.3
Triclinic, P 1
a = 6.7523 (3) Å
b = 8.2926 (3) Å
c = 9.7297 (4) Å
= 100.630 (3)°
= 90.885 (3)°
= 99.168 (3)°
V = 528.05 (4) Å³
Z = 1
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.852, T_max = 0.888
8499 measured reflections
4769 independent reflections
4203 reflections with I > 3(I)
R_int = 0.018

Refinement

R[F² > 2(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
_max = 0.19 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 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-H2n2O1, N5-H2n5O2, N10-H1n10O3.

D-HA	D-H	HA	DA	D-HA
O11-H1o11O21	0.80 (3)	1.72 (4)	2.515 (3)	174 (4)
Ow-H1owO13	0.82 (2)	1.957 (19)	2.754 (3)	164 (2)
Ow-H2owO22ⁱ	0.82 (2)	2.253 (17)	3.037 (3)	160 (3)
Ow-H2owO23ⁱ	0.82 (2)	2.41 (3)	3.023 (3)	132 (3)

N1-H1n1Ow	0.860 (18)	2.302 (15)	3.022 (4)	141 (2)
N1-H2n1O1ⁱⁱ	0.861 (17)	2.24 (2)	2.795 (3)	122.4 (15)
N1-H2n1O23ⁱⁱⁱ	0.861 (15)	2.431 (14)	3.141 (3)	140.3 (18)
N6-H2n6O2ⁱⁱ	0.860 (17)	2.23 (2)	2.750 (3)	119.0 (15)
N6-H2n6O12^iv	0.860 (17)	2.491 (15)	3.200 (3)	140.3 (17)
N6-H1n6O11	0.861 (19)	2.28 (2)	3.141 (3)	174 (2)
N9-H2n9O21^iv	0.860 (17)	2.08 (2)	2.916 (2)	164 (2)
N9-H1n9F2^v	0.860 (7)	2.479 (19)	3.096 (2)	129 (2)
N9-H1n9O3	0.860 (7)	2.01 (2)	2.634 (2)	129 (2)

N2-H2n2Ow	0.861 (16)	2.12 (2)	2.894 (3)	150 (2)
N2-H1n2O1	0.861 (12)	1.94 (2)	2.618 (3)	135 (2)
N5-H2n5O13	0.862 (19)	2.07 (2)	2.906 (3)	165 (2)
N5-H1n5O2	0.860 (7)	2.03 (2)	2.646 (3)	128 (2)
N10-H1n10O21^iv	0.860 (13)	2.595 (10)	3.318 (3)	142.5 (17)
N10-H2n10O3^vi	0.861 (13)	2.186 (14)	2.750 (3)	122.9 (11)
N10-H2n10O22	0.861 (13)	2.524 (13)	3.209 (3)	137.1 (11)

N3-H1n3O23ⁱⁱⁱ	0.89	1.95	2.770 (3)	153
N7-H1n7O12^iv	0.89	1.93	2.807 (3)	166
N11-H1n11O22	0.89	1.93	2.804 (3)	166

N4-H1n4O23^vii	0.860 (14)	2.386 (16)	3.170 (3)	152 (2)
N4-H2n4Ow^iv	0.86 (2)	2.32 (2)	3.173 (3)	176 (2)
N8-H2n8O13^iv	0.857 (16)	2.024 (16)	2.877 (3)	173.8 (15)
N8-H1n8O12^viii	0.860 (10)	2.179 (10)	3.034 (3)	173 (3)
N12-H1n12O21	0.859 (11)	2.115 (16)	2.972 (2)	175 (3)
N12-H2n12O22ⁱⁱ	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); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006); molecular graphics: PLATON (Spek, 2009), DIAMOND (Brandenburg, 2010) and Origin (OriginLab, 2000); 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

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organic compounds