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The structure of the title compound, H3NCH2CH2NH32+·FPO32−, has been determined at 150 K. Ions are connected by N—H...O hydrogen bonds, with the F atom involved in a weak C—H...F hydrogen bond (F...H = 2.48 Å). The ethyl­enediammonium dication is present in its less common conformation, with an N—C—C—N torsion angle of −65.92 (14)°. A reversible glass-like phase transition is observed at 197±2 K; however, the crystal structures determined at 292 and 150 K are similar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025396/bh2026sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025396/bh2026Isup2.hkl
Contains datablock I

CCDC reference: 618775

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.076
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: JANA2000 (Petříček et al., 2005); program(s) used to refine structure: JANA2000; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: JANA2000.

Ethylenediammonium fluorotrioxophosphate top
Crystal data top
C2H10N22+·FO3P2F(000) = 672
Mr = 160.1Dx = 1.548 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 16882 reflections
a = 6.7916 (10) Åθ = 3.2–28.2°
b = 12.694 (9) ŵ = 0.37 mm1
c = 15.930 (7) ÅT = 150 K
V = 1373.4 (12) Å3Plate, colourless
Z = 80.41 × 0.32 × 0.25 mm
Data collection top
Oxford Diffraction XCalibur-2 CCD
diffractometer
1259 reflections with I > 3σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.017
Graphite monochromatorθmax = 28.2°, θmin = 3.2°
Detector resolution: 8.3438 pixels mm-1h = 88
ω scansk = 1616
16882 measured reflectionsl = 2020
1588 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F > 3σ(F)] = 0.025Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
wR(F) = 0.076(Δ/σ)max = 0.001
S = 1.41Δρmax = 0.23 e Å3
1588 reflectionsΔρmin = 0.25 e Å3
101 parametersExtinction correction: B–C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraintsExtinction coefficient: 0.0029 (8)
22 constraints
Special details top

Refinement. There were calculated 3 refinements that differed by the number of constrained parameters regarding the ammonium H atoms while the other conditions of the refinement remained the same. In the first refinement all the H atoms in the structure were constrained. C—H and N—H distances were constrained to 0.97 and 0.89 Å, respectively. The hydrogen displacement parameters in the riding motion approximation (Busing & Levy, 1964) were constrained to 1.5 and 1.2 multiples of the equivalent isotropic displacement parameters of the adjacent N and C atoms, respectively. The number of the refined parameters equalled to 83. The indicators of the refinement are as following: Sobs=1.61, Sall=1.44, Robs=0.0247, Rwobs=0.0768, Rall=0.0312, Rwall=0.0781.

The second refinement the results of which are given in detail in the CIF differed by removal of constraints regarding the tetrahedral geometry and distances of the ammonium H atoms. The displacement parameters of the ammonium H atoms in the riding motion approximation (Busing & Levy, 1964) were constrained to 1.5. The methylene H atoms were treated in the same way as in the first case.

Finally, in the third refinement the ammonium H atoms were treated as independent atoms and their displacement parameters were refined isotropically. There were 107 refined parameters. The methylene H atoms were treated in the same way as in the first case. The indicators of the refinement are as following: Sobs=1.57, Sall=1.41, Robs=0.0247, Rwobs=0.0743, Rall=0.0313, Rwall=0.0755.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.16714 (5)0.39257 (2)0.635851 (19)0.01179 (11)
O10.00000 (13)0.39113 (7)0.57290 (6)0.0169 (3)
O20.18329 (13)0.49619 (7)0.68302 (5)0.0165 (3)
O30.35991 (13)0.35141 (7)0.60172 (6)0.0193 (3)
F10.10343 (13)0.30908 (6)0.70552 (5)0.0255 (3)
N10.33205 (17)0.51592 (9)0.35706 (7)0.0139 (3)
C10.3754 (2)0.41103 (10)0.39430 (8)0.0164 (4)
C20.2279 (2)0.32721 (11)0.36971 (8)0.0182 (4)
N20.02547 (16)0.34636 (9)0.40335 (7)0.0138 (3)
H1n10.435 (3)0.5583 (13)0.3697 (9)0.0209*
H2n10.322 (2)0.5076 (11)0.3003 (11)0.0209*
H3n10.212 (3)0.5431 (13)0.3802 (9)0.0209*
H1n20.045 (2)0.2841 (14)0.3976 (10)0.0208*
H2n20.029 (2)0.3613 (12)0.4594 (11)0.0208*
H3n20.043 (2)0.3982 (12)0.3732 (9)0.0208*
H1c10.3797370.4170180.454970.0197*
H2c10.5064380.3888450.3777850.0197*
H1c20.2223610.3217990.3090180.0218*
H2c20.2742880.2589140.388530.0218*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01110 (19)0.01060 (19)0.01367 (19)0.00051 (11)0.00086 (12)0.00063 (11)
O10.0141 (5)0.0212 (5)0.0155 (5)0.0007 (4)0.0021 (4)0.0022 (4)
O20.0194 (5)0.0140 (5)0.0162 (5)0.0016 (4)0.0021 (3)0.0017 (3)
O30.0134 (5)0.0155 (5)0.0288 (5)0.0031 (4)0.0002 (4)0.0040 (4)
F10.0303 (5)0.0224 (4)0.0238 (4)0.0064 (4)0.0017 (4)0.0098 (3)
N10.0123 (5)0.0148 (5)0.0147 (6)0.0008 (4)0.0006 (4)0.0004 (4)
C10.0138 (6)0.0178 (6)0.0178 (7)0.0010 (5)0.0003 (5)0.0034 (5)
C20.0172 (6)0.0147 (6)0.0228 (7)0.0023 (5)0.0034 (5)0.0020 (5)
N20.0148 (5)0.0114 (5)0.0154 (6)0.0012 (4)0.0004 (4)0.0005 (4)
Geometric parameters (Å, º) top
P1—O11.5147 (9)C1—H1C10.97
P1—O21.5188 (9)C1—H2C10.97
P1—O31.5108 (9)C2—N21.4952 (17)
P1—F11.5945 (8)C2—H1C20.97
N1—C11.4871 (17)C2—H2C20.97
N1—H1N10.907 (17)N2—H1N20.928 (17)
N1—H2N10.912 (17)N2—H2N20.913 (17)
N1—H3N10.958 (17)N2—H3N20.937 (16)
C1—C21.5129 (19)
O1—P1—O2113.08 (5)C2—C1—H1C1109.47
O1—P1—O3114.02 (5)C2—C1—H2C1109.47
O1—P1—F1104.45 (5)H1c1—C1—H2c1105.36
O2—P1—O3114.51 (5)C1—C2—N2113.68 (11)
O2—P1—F1104.53 (5)C1—C2—H1C2109.47
O3—P1—F1104.82 (5)C1—C2—H2C2109.47
C1—N1—H1N1106.8 (10)N2—C2—H1C2109.47
C1—N1—H2N1107.9 (9)N2—C2—H2C2109.47
C1—N1—H3N1109.7 (10)H1C2—C2—H2C2104.91
H1N1—N1—H2N1110.3 (13)C2—N2—H1N2107.4 (10)
H1N1—N1—H3N1111.1 (14)C2—N2—H2N2111.0 (9)
H2N1—N1—H3N1110.9 (13)C2—N2—H3N2112.6 (10)
N1—C1—C2113.29 (11)H1N2—N2—H2N2106.7 (14)
N1—C1—H1C1109.47H1N2—N2—H3N2107.1 (14)
N1—C1—H2C1109.47H2N2—N2—H3N2111.7 (13)
N1—C1—C2—N265.92 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1C1···O30.972.493.3915 (16)155
C2—H1C2···F1i0.972.483.2478 (15)136
N1—H1N1···O3ii0.91 (2)1.86 (2)2.7648 (14)178 (2)
N1—H2N1···O2iii0.91 (2)1.87 (2)2.7786 (14)174 (1)
N1—H3N1···O1iv0.96 (2)1.83 (2)2.7790 (14)173 (2)
N2—H1N2···O3v0.93 (2)1.84 (2)2.7520 (14)168 (2)
N2—H2N2···O10.91 (2)1.86 (2)2.7655 (15)172 (1)
N2—H3N2···O2iv0.94 (2)1.87 (2)2.8104 (14)178 (1)
C2—H2C2···O1vi0.972.523.4545 (16)161
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1, z+1; (iii) x+1/2, y+1, z1/2; (iv) x, y+1, z+1; (v) x1/2, y+1/2, z+1; (vi) x+1/2, y+1/2, z+1.
 

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