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The title compound, tris(2-ammonioethyl)amine dihydrogenphosphate monohydrogenphosphate, C
6H
21N
43+·HPO
42−·H
2PO
4−, was prepared hydrothermally at 413 K over a period of 15 d. The structure exhibits extended polyanions, [(HPO
4)(H
2PO
4)]
n3n−, constructed as O—H
O hydrogen-bonded ribbons. The triprotonated amine cations connect adjacent ribbons
via N—H
O hydrogen bonds, giving rise to molecular sheets parallel to (010).
Supporting information
CCDC reference: 259119
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.103
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ?
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for P2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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: CAD-4 EXPRESS (Duisenberg, 1992); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Crystal data top
C6H21N43+·HO4P2−·H2O4P− | Z = 2 |
Mr = 342.23 | F(000) = 364 |
Triclinic, P1 | Dx = 1.500 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.905 (2) Å | Cell parameters from 25 reflections |
b = 9.441 (2) Å | θ = 5.3–7.5° |
c = 10.974 (3) Å | µ = 0.33 mm−1 |
α = 76.37 (2)° | T = 293 K |
β = 101.29 (3)° | Parallelepiped, colourless |
γ = 105.96 (3)° | 0.26 × 0.19 × 0.10 mm |
V = 757.7 (3) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.012 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.3° |
Graphite monochromator | h = 0→10 |
non–profiled ω/2θ scans | k = −12→11 |
3534 measured reflections | l = −14→13 |
3290 independent reflections | 2 standard reflections every 120 min |
2774 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.417P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3290 reflections | Δρmax = 0.33 e Å−3 |
186 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (3) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.79099 (6) | 0.64482 (5) | 0.11166 (4) | 0.02252 (14) | |
O1 | 0.76078 (19) | 0.48820 (15) | 0.19129 (13) | 0.0307 (3) | |
O2 | 0.84175 (19) | 0.65517 (18) | −0.01655 (13) | 0.0343 (3) | |
O3 | 0.61853 (19) | 0.70627 (18) | 0.08243 (13) | 0.0341 (3) | |
H3 | 0.5625 | 0.6736 | 0.1427 | 0.050* | |
O4 | 0.9331 (2) | 0.75937 (17) | 0.18438 (16) | 0.0433 (4) | |
H4 | 1.0042 | 0.7162 | 0.2330 | 0.050* | |
P2 | 0.33103 (6) | 0.61675 (5) | 0.35095 (4) | 0.02156 (14) | |
O5 | 0.29736 (18) | 0.44763 (15) | 0.40564 (14) | 0.0330 (3) | |
O6 | 0.1736 (2) | 0.67682 (18) | 0.35782 (13) | 0.0347 (3) | |
O7 | 0.4939 (2) | 0.70097 (17) | 0.43745 (16) | 0.0425 (4) | |
H7 | 0.5555 | 0.6428 | 0.4753 | 0.050* | |
O8 | 0.3745 (2) | 0.6496 (2) | 0.21744 (14) | 0.0408 (4) | |
N | 0.6682 (2) | 0.12622 (17) | 0.26230 (14) | 0.0237 (3) | |
N1 | 0.8058 (2) | 0.29896 (19) | 0.02464 (15) | 0.0278 (4) | |
H1A | 0.7906 | 0.3375 | −0.0578 | 0.042* | |
H1B | 0.9214 | 0.3170 | 0.0539 | 0.042* | |
H1C | 0.7518 | 0.3411 | 0.0654 | 0.042* | |
N2 | 0.9325 (2) | 0.33635 (18) | 0.41843 (15) | 0.0264 (3) | |
H2A | 1.0442 | 0.3857 | 0.4386 | 0.042* | |
H2B | 0.8647 | 0.3469 | 0.4700 | 0.042* | |
H2C | 0.8930 | 0.3734 | 0.3388 | 0.042* | |
N3 | 0.4085 (2) | 0.32140 (18) | 0.22607 (15) | 0.0272 (3) | |
H3A | 0.3504 | 0.3686 | 0.2588 | 0.042* | |
H3B | 0.3696 | 0.3272 | 0.1437 | 0.042* | |
H3C | 0.5243 | 0.3643 | 0.2371 | 0.042* | |
C1 | 0.7499 (3) | 0.0618 (2) | 0.1846 (2) | 0.0319 (4) | |
H1D | 0.6959 | −0.0450 | 0.1933 | 0.0416 (19)* | |
H1E | 0.8755 | 0.0740 | 0.2164 | 0.0416 (19)* | |
C2 | 0.7287 (3) | 0.1345 (2) | 0.04544 (19) | 0.0322 (4) | |
H2D | 0.7865 | 0.0893 | −0.0003 | 0.0416 (19)* | |
H2E | 0.6033 | 0.1154 | 0.0117 | 0.0416 (19)* | |
C3 | 0.7379 (3) | 0.0842 (2) | 0.39743 (18) | 0.0301 (4) | |
H3D | 0.7378 | −0.0215 | 0.4167 | 0.0416 (19)* | |
H3E | 0.6599 | 0.0989 | 0.4490 | 0.0416 (19)* | |
C4 | 0.9250 (3) | 0.1755 (2) | 0.4314 (2) | 0.0324 (4) | |
H4A | 0.9696 | 0.1360 | 0.5181 | 0.0416 (19)* | |
H4B | 1.0017 | 0.1649 | 0.3768 | 0.0416 (19)* | |
C5 | 0.4730 (3) | 0.0736 (2) | 0.2397 (2) | 0.0304 (4) | |
H5A | 0.4393 | −0.0315 | 0.2794 | 0.0416 (19)* | |
H5B | 0.4347 | 0.0811 | 0.1494 | 0.0416 (19)* | |
C6 | 0.3775 (3) | 0.1616 (2) | 0.2904 (2) | 0.0311 (4) | |
H6A | 0.2509 | 0.1160 | 0.2794 | 0.0416 (19)* | |
H6B | 0.4176 | 0.1561 | 0.3804 | 0.0416 (19)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0207 (2) | 0.0239 (2) | 0.0223 (2) | 0.00700 (18) | 0.00197 (17) | −0.00190 (18) |
O1 | 0.0308 (7) | 0.0262 (7) | 0.0319 (7) | 0.0074 (6) | 0.0035 (6) | 0.0006 (6) |
O2 | 0.0264 (7) | 0.0505 (9) | 0.0273 (7) | 0.0129 (6) | 0.0072 (6) | −0.0033 (6) |
O3 | 0.0293 (7) | 0.0466 (9) | 0.0295 (7) | 0.0201 (7) | 0.0086 (6) | 0.0037 (6) |
O4 | 0.0471 (9) | 0.0271 (7) | 0.0469 (10) | 0.0106 (7) | −0.0181 (7) | −0.0083 (7) |
P2 | 0.0204 (2) | 0.0260 (2) | 0.0187 (2) | 0.00759 (18) | 0.00050 (17) | −0.00442 (17) |
O5 | 0.0262 (7) | 0.0270 (7) | 0.0390 (8) | 0.0046 (6) | −0.0037 (6) | −0.0021 (6) |
O6 | 0.0360 (8) | 0.0517 (9) | 0.0252 (7) | 0.0255 (7) | 0.0004 (6) | −0.0102 (6) |
O7 | 0.0437 (9) | 0.0270 (7) | 0.0477 (10) | 0.0107 (7) | −0.0216 (7) | −0.0103 (7) |
O8 | 0.0323 (8) | 0.0684 (11) | 0.0248 (7) | 0.0186 (8) | 0.0090 (6) | −0.0030 (7) |
N | 0.0260 (8) | 0.0209 (7) | 0.0243 (8) | 0.0059 (6) | 0.0044 (6) | −0.0037 (6) |
N1 | 0.0239 (8) | 0.0355 (9) | 0.0248 (8) | 0.0069 (7) | 0.0053 (6) | −0.0061 (7) |
N2 | 0.0233 (8) | 0.0303 (8) | 0.0245 (8) | 0.0045 (6) | 0.0042 (6) | −0.0049 (6) |
N3 | 0.0258 (8) | 0.0300 (8) | 0.0284 (8) | 0.0106 (7) | 0.0027 (6) | −0.0069 (7) |
C1 | 0.0384 (11) | 0.0284 (10) | 0.0345 (11) | 0.0142 (8) | 0.0069 (9) | −0.0079 (8) |
C2 | 0.0344 (11) | 0.0345 (11) | 0.0309 (10) | 0.0065 (9) | 0.0056 (8) | −0.0133 (8) |
C3 | 0.0359 (11) | 0.0255 (9) | 0.0256 (9) | 0.0067 (8) | 0.0029 (8) | −0.0001 (7) |
C4 | 0.0319 (10) | 0.0354 (11) | 0.0330 (11) | 0.0148 (8) | −0.0006 (8) | −0.0089 (8) |
C5 | 0.0279 (10) | 0.0238 (9) | 0.0389 (11) | 0.0034 (8) | 0.0039 (8) | −0.0087 (8) |
C6 | 0.0283 (10) | 0.0326 (10) | 0.0322 (10) | 0.0061 (8) | 0.0115 (8) | −0.0017 (8) |
Geometric parameters (Å, º) top
P1—O2 | 1.5116 (15) | N2—H2C | 0.8900 |
P1—O1 | 1.5118 (14) | N3—C6 | 1.482 (2) |
P1—O4 | 1.5671 (16) | N3—H3A | 0.8900 |
P1—O3 | 1.5729 (15) | N3—H3B | 0.8900 |
O3—H3 | 0.8200 | N3—H3C | 0.8900 |
O4—H4 | 0.8200 | C1—C2 | 1.516 (3) |
P2—O8 | 1.5117 (15) | C1—H1D | 0.9700 |
P2—O6 | 1.5231 (15) | C1—H1E | 0.9700 |
P2—O5 | 1.5354 (15) | C2—H2D | 0.9700 |
P2—O7 | 1.5826 (16) | C2—H2E | 0.9700 |
O7—H7 | 0.8200 | C3—C4 | 1.518 (3) |
N—C5 | 1.475 (3) | C3—H3D | 0.9700 |
N—C3 | 1.478 (2) | C3—H3E | 0.9700 |
N—C1 | 1.480 (2) | C4—H4A | 0.9700 |
N1—C2 | 1.484 (3) | C4—H4B | 0.9700 |
N1—H1A | 0.8900 | C5—C6 | 1.516 (3) |
N1—H1B | 0.8900 | C5—H5A | 0.9700 |
N1—H1C | 0.8900 | C5—H5B | 0.9700 |
N2—C4 | 1.477 (3) | C6—H6A | 0.9700 |
N2—H2A | 0.8900 | C6—H6B | 0.9700 |
N2—H2B | 0.8900 | | |
| | | |
O2—P1—O1 | 113.86 (9) | N—C1—C2 | 112.86 (16) |
O2—P1—O4 | 109.98 (10) | N—C1—H1D | 109.0 |
O1—P1—O4 | 111.09 (9) | C2—C1—H1D | 109.0 |
O2—P1—O3 | 105.03 (8) | N—C1—H1E | 109.0 |
O1—P1—O3 | 111.70 (9) | C2—C1—H1E | 109.0 |
O4—P1—O3 | 104.63 (9) | H1D—C1—H1E | 107.8 |
P1—O3—H3 | 109.5 | N1—C2—C1 | 112.14 (16) |
P1—O4—H4 | 109.5 | N1—C2—H2D | 109.2 |
O8—P2—O6 | 111.98 (9) | C1—C2—H2D | 109.2 |
O8—P2—O5 | 110.52 (10) | N1—C2—H2E | 109.2 |
O6—P2—O5 | 110.84 (9) | C1—C2—H2E | 109.2 |
O8—P2—O7 | 109.20 (10) | H2D—C2—H2E | 107.9 |
O6—P2—O7 | 105.76 (9) | N—C3—C4 | 112.37 (16) |
O5—P2—O7 | 108.37 (8) | N—C3—H3D | 109.1 |
P2—O7—H7 | 109.5 | C4—C3—H3D | 109.1 |
C5—N—C3 | 111.24 (15) | N—C3—H3E | 109.1 |
C5—N—C1 | 109.90 (15) | C4—C3—H3E | 109.1 |
C3—N—C1 | 109.57 (15) | H3D—C3—H3E | 107.9 |
C2—N1—H1A | 109.5 | N2—C4—C3 | 112.38 (16) |
C2—N1—H1B | 109.5 | N2—C4—H4A | 109.1 |
H1A—N1—H1B | 109.5 | C3—C4—H4A | 109.1 |
C2—N1—H1C | 109.5 | N2—C4—H4B | 109.1 |
H1A—N1—H1C | 109.5 | C3—C4—H4B | 109.1 |
H1B—N1—H1C | 109.5 | H4A—C4—H4B | 107.9 |
C4—N2—H2A | 109.5 | N—C5—C6 | 113.20 (16) |
C4—N2—H2B | 109.5 | N—C5—H5A | 108.9 |
H2A—N2—H2B | 109.5 | C6—C5—H5A | 108.9 |
C4—N2—H2C | 109.5 | N—C5—H5B | 108.9 |
H2A—N2—H2C | 109.5 | C6—C5—H5B | 108.9 |
H2B—N2—H2C | 109.5 | H5A—C5—H5B | 107.8 |
C6—N3—H3A | 109.5 | N3—C6—C5 | 112.56 (16) |
C6—N3—H3B | 109.5 | N3—C6—H6A | 109.1 |
H3A—N3—H3B | 109.5 | C5—C6—H6A | 109.1 |
C6—N3—H3C | 109.5 | N3—C6—H6B | 109.1 |
H3A—N3—H3C | 109.5 | C5—C6—H6B | 109.1 |
H3B—N3—H3C | 109.5 | H6A—C6—H6B | 107.8 |
| | | |
C5—N—C1—C2 | 74.1 (2) | N—C3—C4—N2 | 65.3 (2) |
C3—N—C1—C2 | −163.34 (16) | C3—N—C5—C6 | 72.2 (2) |
N—C1—C2—N1 | 57.8 (2) | C1—N—C5—C6 | −166.28 (16) |
C5—N—C3—C4 | −162.07 (16) | N—C5—C6—N3 | 63.9 (2) |
C1—N—C3—C4 | 76.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O8 | 0.82 | 1.77 | 2.526 (2) | 152 |
N1—H1C···O1 | 0.89 | 2.16 | 2.968 (2) | 151 |
N2—H2C···O1 | 0.89 | 2.01 | 2.859 (2) | 160 |
N3—H3A···O5 | 0.89 | 2.08 | 2.905 (2) | 153 |
N3—H3A···O8 | 0.89 | 2.54 | 3.161 (3) | 127 |
N3—H3C···O1 | 0.89 | 2.00 | 2.846 (2) | 158 |
O4—H4···O6i | 0.82 | 1.77 | 2.558 (2) | 161 |
O7—H7···O5ii | 0.82 | 1.79 | 2.584 (2) | 162 |
N1—H1A···O8iii | 0.89 | 1.97 | 2.760 (2) | 147 |
N1—H1B···O2iv | 0.89 | 1.93 | 2.715 (2) | 146 |
N2—H2A···O5i | 0.89 | 2.00 | 2.804 (2) | 149 |
N3—H3B···O2iii | 0.89 | 1.97 | 2.733 (2) | 142 |
N3—H3B···O3iii | 0.89 | 2.60 | 3.417 (2) | 154 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z. |
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