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The structure of the title compound, H
3NCH
2CH
2NH
32+·FPO
32−, 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
CCDC reference: 618775
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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+·FO3P2− | F(000) = 672 |
Mr = 160.1 | Dx = 1.548 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 16882 reflections |
a = 6.7916 (10) Å | θ = 3.2–28.2° |
b = 12.694 (9) Å | µ = 0.37 mm−1 |
c = 15.930 (7) Å | T = 150 K |
V = 1373.4 (12) Å3 | Plate, colourless |
Z = 8 | 0.41 × 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 Source | Rint = 0.017 |
Graphite monochromator | θmax = 28.2°, θmin = 3.2° |
Detector resolution: 8.3438 pixels mm-1 | h = −8→8 |
ω scans | k = −16→16 |
16882 measured reflections | l = −20→20 |
1588 independent reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F > 3σ(F)] = 0.025 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
wR(F) = 0.076 | (Δ/σ)max = 0.001 |
S = 1.41 | Δρmax = 0.23 e Å−3 |
1588 reflections | Δρmin = −0.25 e Å−3 |
101 parameters | Extinction correction: B–C type 1 Lorentzian isotropic (Becker & Coppens, 1974) |
0 restraints | Extinction 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 | x | y | z | Uiso*/Ueq | |
P1 | 0.16714 (5) | 0.39257 (2) | 0.635851 (19) | 0.01179 (11) | |
O1 | 0.00000 (13) | 0.39113 (7) | 0.57290 (6) | 0.0169 (3) | |
O2 | 0.18329 (13) | 0.49619 (7) | 0.68302 (5) | 0.0165 (3) | |
O3 | 0.35991 (13) | 0.35141 (7) | 0.60172 (6) | 0.0193 (3) | |
F1 | 0.10343 (13) | 0.30908 (6) | 0.70552 (5) | 0.0255 (3) | |
N1 | 0.33205 (17) | 0.51592 (9) | 0.35706 (7) | 0.0139 (3) | |
C1 | 0.3754 (2) | 0.41103 (10) | 0.39430 (8) | 0.0164 (4) | |
C2 | 0.2279 (2) | 0.32721 (11) | 0.36971 (8) | 0.0182 (4) | |
N2 | 0.02547 (16) | 0.34636 (9) | 0.40335 (7) | 0.0138 (3) | |
H1n1 | 0.435 (3) | 0.5583 (13) | 0.3697 (9) | 0.0209* | |
H2n1 | 0.322 (2) | 0.5076 (11) | 0.3003 (11) | 0.0209* | |
H3n1 | 0.212 (3) | 0.5431 (13) | 0.3802 (9) | 0.0209* | |
H1n2 | −0.045 (2) | 0.2841 (14) | 0.3976 (10) | 0.0208* | |
H2n2 | 0.029 (2) | 0.3613 (12) | 0.4594 (11) | 0.0208* | |
H3n2 | −0.043 (2) | 0.3982 (12) | 0.3732 (9) | 0.0208* | |
H1c1 | 0.379737 | 0.417018 | 0.45497 | 0.0197* | |
H2c1 | 0.506438 | 0.388845 | 0.377785 | 0.0197* | |
H1c2 | 0.222361 | 0.321799 | 0.309018 | 0.0218* | |
H2c2 | 0.274288 | 0.258914 | 0.38853 | 0.0218* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01110 (19) | 0.01060 (19) | 0.01367 (19) | 0.00051 (11) | −0.00086 (12) | 0.00063 (11) |
O1 | 0.0141 (5) | 0.0212 (5) | 0.0155 (5) | 0.0007 (4) | −0.0021 (4) | −0.0022 (4) |
O2 | 0.0194 (5) | 0.0140 (5) | 0.0162 (5) | 0.0016 (4) | −0.0021 (3) | −0.0017 (3) |
O3 | 0.0134 (5) | 0.0155 (5) | 0.0288 (5) | 0.0031 (4) | 0.0002 (4) | −0.0040 (4) |
F1 | 0.0303 (5) | 0.0224 (4) | 0.0238 (4) | −0.0064 (4) | −0.0017 (4) | 0.0098 (3) |
N1 | 0.0123 (5) | 0.0148 (5) | 0.0147 (6) | −0.0008 (4) | 0.0006 (4) | −0.0004 (4) |
C1 | 0.0138 (6) | 0.0178 (6) | 0.0178 (7) | 0.0010 (5) | −0.0003 (5) | 0.0034 (5) |
C2 | 0.0172 (6) | 0.0147 (6) | 0.0228 (7) | 0.0023 (5) | 0.0034 (5) | −0.0020 (5) |
N2 | 0.0148 (5) | 0.0114 (5) | 0.0154 (6) | −0.0012 (4) | −0.0004 (4) | −0.0005 (4) |
Geometric parameters (Å, º) top
P1—O1 | 1.5147 (9) | C1—H1C1 | 0.97 |
P1—O2 | 1.5188 (9) | C1—H2C1 | 0.97 |
P1—O3 | 1.5108 (9) | C2—N2 | 1.4952 (17) |
P1—F1 | 1.5945 (8) | C2—H1C2 | 0.97 |
N1—C1 | 1.4871 (17) | C2—H2C2 | 0.97 |
N1—H1N1 | 0.907 (17) | N2—H1N2 | 0.928 (17) |
N1—H2N1 | 0.912 (17) | N2—H2N2 | 0.913 (17) |
N1—H3N1 | 0.958 (17) | N2—H3N2 | 0.937 (16) |
C1—C2 | 1.5129 (19) | | |
| | | |
O1—P1—O2 | 113.08 (5) | C2—C1—H1C1 | 109.47 |
O1—P1—O3 | 114.02 (5) | C2—C1—H2C1 | 109.47 |
O1—P1—F1 | 104.45 (5) | H1c1—C1—H2c1 | 105.36 |
O2—P1—O3 | 114.51 (5) | C1—C2—N2 | 113.68 (11) |
O2—P1—F1 | 104.53 (5) | C1—C2—H1C2 | 109.47 |
O3—P1—F1 | 104.82 (5) | C1—C2—H2C2 | 109.47 |
C1—N1—H1N1 | 106.8 (10) | N2—C2—H1C2 | 109.47 |
C1—N1—H2N1 | 107.9 (9) | N2—C2—H2C2 | 109.47 |
C1—N1—H3N1 | 109.7 (10) | H1C2—C2—H2C2 | 104.91 |
H1N1—N1—H2N1 | 110.3 (13) | C2—N2—H1N2 | 107.4 (10) |
H1N1—N1—H3N1 | 111.1 (14) | C2—N2—H2N2 | 111.0 (9) |
H2N1—N1—H3N1 | 110.9 (13) | C2—N2—H3N2 | 112.6 (10) |
N1—C1—C2 | 113.29 (11) | H1N2—N2—H2N2 | 106.7 (14) |
N1—C1—H1C1 | 109.47 | H1N2—N2—H3N2 | 107.1 (14) |
N1—C1—H2C1 | 109.47 | H2N2—N2—H3N2 | 111.7 (13) |
| | | |
N1—C1—C2—N2 | −65.92 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C1···O3 | 0.97 | 2.49 | 3.3915 (16) | 155 |
C2—H1C2···F1i | 0.97 | 2.48 | 3.2478 (15) | 136 |
N1—H1N1···O3ii | 0.91 (2) | 1.86 (2) | 2.7648 (14) | 178 (2) |
N1—H2N1···O2iii | 0.91 (2) | 1.87 (2) | 2.7786 (14) | 174 (1) |
N1—H3N1···O1iv | 0.96 (2) | 1.83 (2) | 2.7790 (14) | 173 (2) |
N2—H1N2···O3v | 0.93 (2) | 1.84 (2) | 2.7520 (14) | 168 (2) |
N2—H2N2···O1 | 0.91 (2) | 1.86 (2) | 2.7655 (15) | 172 (1) |
N2—H3N2···O2iv | 0.94 (2) | 1.87 (2) | 2.8104 (14) | 178 (1) |
C2—H2C2···O1vi | 0.97 | 2.52 | 3.4545 (16) | 161 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, −y+1, z−1/2; (iv) −x, −y+1, −z+1; (v) x−1/2, −y+1/2, −z+1; (vi) x+1/2, −y+1/2, −z+1. |
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