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This study reports the structure redeterminations of C5H11NH3+·H2PO4- (n-pentylammonium dihydrogenphos­phate, C5ADP), C6H13NH3+·H2PO4- (n-hexylammonium dihydrogenphosphate, C6ADP) and C9H19NH3+·H2PO4- (n-nonylammonium dihydrogenphosphate, C9ADP). The structures are monoclinic (P21/n), belonging to the series of previously studied structures C2ADP-C8ADP and C10ADP. The structures exhibit reproducible ferroelastic switching. There are hydrogen bonds between the dihydrogenphos­phates and the n-alkylammonium groups. Among them there are two hydrogen bonds with hydrogens which hop from the donor to the acceptor oxygens during the ferroelastic switching. C5ADP as well as C3ADP differ from the other members of the series by packing of the double layers of the dihydrogenphosphates. Moreover, the packing of n-alkyl­ammonium molecules in all these structures depends on the parity of the number of atoms in the n-alkylammonium chains. All the samples contained two domains and their structures were refined as twins.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100007941/na0106sup1.cif
Contains datablocks global, C5ADP, C6ADP, C9ADP

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007941/na0106c5adpsup2.hkl
Contains datablock c5adp

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007941/na0106c6adpsup3.hkl
Contains datablock c6adp

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007941/na0106c9adpsup4.hkl
Contains datablock c9adp

CCDC references: 153348; 153349; 153350

Refinement top

The structure is a superstucture and a ferroelastic structure as well which can be related to the prototypic space group P 2/b 21/n 21/a

Computing details top

Data collection: Enraf-Nonius Software for C5ADP; HW, Petříček, 1998 for C6ADP, C9ADP. Cell refinement: Enraf-Nonius Software for C5ADP; HW, Petříček, 1998 for C6ADP, C9ADP. For all compounds, data reduction: JANA98, Petříček & Dušek, 1998. Program(s) used to solve structure: SHELXS86, Sheldrick, 1986 for C5ADP, C6ADP; JANA98, Petříček & Dušek, 1998 for C9ADP. For all compounds, program(s) used to refine structure: JANA98, Petříček & Dušek, 1998; molecular graphics: PICTUR (Dušek, 1993); software used to prepare material for publication: JANA98, Petříček & Dušek, 1998.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(C5ADP) top
Crystal data top
C5H14N+·H2O4PF(000) = 800
Mr = 185.16Dx = 1.361 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 9.149 (2) Åθ = 9–15°
b = 27.081 (3) ŵ = 0.28 mm1
c = 7.290 (1) ÅT = 290 K
β = 90.82 (1)°Plate, colourless
V = 1806.2 (5) Å30.56 × 0.32 × 0.15 mm
Z = 8
Data collection top
Enraf-Nonius CAD-4-MACHIII-PC
diffractometer
θmax = 25°
ω–2θ scansh = 1010
3418 measured reflectionsk = 032
3167 independent reflectionsl = 08
2417 reflections with I > 3σ(I)3 standard reflections every 3600 min
Rint = 0.034 intensity decay: 2.2%
Refinement top
Refinement on FAll H-atom parameters refined
Least-squares matrix: full with fixed elements per cyclew = (σ2(Fo) + 0.0001(Fo)2)-1
R[F2 > 2σ(F2)] = 0.040(Δ/σ)max = 0.01
wR(F2) = 0.055Δρmax = 0.33 e Å3
S = 2.58Δρmin = 0.34 e Å3
3167 reflectionsExtinction correction: Becker & Coppens, 1974, type II
329 parametersExtinction coefficient: 0.00030 (4)
0 constraints
Crystal data top
C5H14N+·H2O4PV = 1806.2 (5) Å3
Mr = 185.16Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.149 (2) ŵ = 0.28 mm1
b = 27.081 (3) ÅT = 290 K
c = 7.290 (1) Å0.56 × 0.32 × 0.15 mm
β = 90.82 (1)°
Data collection top
Enraf-Nonius CAD-4-MACHIII-PC
diffractometer
Rint = 0.034
3418 measured reflections3 standard reflections every 3600 min
3167 independent reflections intensity decay: 2.2%
2417 reflections with I > 3σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.040329 parameters
wR(F2) = 0.055All H-atom parameters refined
S = 2.58Δρmax = 0.33 e Å3
3167 reflectionsΔρmin = 0.34 e Å3
Special details top

Refinement. The structure was refined as a twin. domain fraction f of the minor domain: 0.080 (4) from measured intensities of 90 pairs of separated reflections: 0.114 (1)

The twinning matrix is given in _diffrn_reflns_transf_matrix items

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.31308 (4)0.30565 (1)0.25595 (5)0.0222 (1)
O110.1925 (1)0.34584 (4)0.2291 (2)0.0362 (4)
O210.3426 (1)0.29679 (4)0.4567 (1)0.0337 (4)
O310.4408 (1)0.32108 (4)0.1431 (1)0.0310 (3)
O410.2482 (1)0.25574 (4)0.1807 (1)0.0314 (3)
P20.80901 (4)0.30250 (1)0.26376 (5)0.0230 (1)
O120.6972 (1)0.34574 (4)0.2676 (2)0.0365 (4)
O220.8409 (1)0.29344 (4)0.0554 (1)0.0366 (4)
O320.9432 (1)0.31934 (4)0.3649 (1)0.0335 (3)
O420.7432 (1)0.25554 (4)0.3394 (1)0.0304 (3)
N10.9668 (2)0.68778 (5)0.2677 (2)0.0302 (4)
C110.8861 (2)0.64032 (6)0.2487 (2)0.0304 (5)
C210.9888 (2)0.59645 (6)0.2543 (2)0.0350 (5)
C310.9045 (2)0.54815 (6)0.2472 (3)0.0382 (6)
C411.0027 (2)0.50263 (6)0.2495 (3)0.0415 (6)
C510.9156 (3)0.45457 (8)0.2453 (3)0.0546 (8)
H1N11.002 (2)0.6887 (7)0.381 (3)0.052 (6)*
H2N10.903 (2)0.7131 (6)0.249 (2)0.026 (4)*
H3N11.035 (2)0.6871 (7)0.197 (3)0.045 (6)*
H1C110.818 (2)0.6389 (6)0.345 (2)0.041 (5)*
H2C110.840 (2)0.6410 (6)0.136 (2)0.032 (4)*
H2C211.050 (2)0.5978 (6)0.365 (2)0.046 (5)*
H1C211.065 (2)0.5984 (6)0.151 (2)0.048 (5)*
H1C310.835 (2)0.5493 (6)0.349 (2)0.040 (5)*
H2C310.843 (2)0.5482 (6)0.152 (2)0.044 (5)*
H2C411.067 (2)0.5063 (6)0.358 (2)0.033 (4)*
H1C411.071 (2)0.5068 (6)0.143 (2)0.039 (5)*
H1C510.851 (2)0.4546 (8)0.346 (3)0.070 (7)*
H2C510.993 (3)0.4289 (9)0.246 (3)0.084 (8)*
H3C510.850 (2)0.4566 (8)0.141 (3)0.070 (7)*
N20.4762 (2)0.68722 (5)0.2260 (2)0.0290 (4)
C120.3915 (2)0.64080 (6)0.2442 (2)0.0310 (5)
C220.4908 (2)0.59622 (6)0.2442 (2)0.0348 (5)
C320.4042 (2)0.54835 (6)0.2504 (3)0.0377 (6)
C420.5012 (2)0.50265 (6)0.2518 (3)0.0405 (6)
C520.4125 (3)0.45490 (8)0.2531 (3)0.0556 (8)
H2N20.418 (2)0.7123 (6)0.237 (2)0.017 (4)*
H1N20.541 (2)0.6870 (7)0.310 (3)0.058 (6)*
H3n20.523 (2)0.6867 (7)0.117 (3)0.052 (6)*
H2C120.341 (2)0.6423 (6)0.352 (2)0.046 (5)*
H1C120.325 (2)0.6406 (6)0.146 (2)0.046 (5)*
H2C220.564 (2)0.5983 (6)0.348 (2)0.050 (5)*
H1C220.561 (2)0.5978 (6)0.145 (2)0.045 (5)*
H1C320.338 (2)0.5488 (6)0.353 (2)0.036 (4)*
H2C320.340 (2)0.5481 (6)0.156 (2)0.042 (5)*
H2C420.573 (2)0.5070 (6)0.359 (2)0.037 (5)*
H1C420.569 (2)0.5062 (6)0.149 (2)0.034 (4)*
H1C520.349 (2)0.4570 (7)0.357 (3)0.064 (6)*
H3C520.346 (3)0.4548 (8)0.143 (3)0.077 (7)*
H2C520.485 (3)0.4287 (8)0.250 (3)0.070 (7)*
HO110.116 (2)0.3398 (7)0.271 (2)0.047 (6)*
HO410.245 (2)0.2527 (7)0.062 (3)0.066 (7)*
HO120.620 (2)0.3399 (7)0.239 (2)0.044 (6)*
HO220.838 (3)0.2587 (8)0.030 (3)0.089 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0205 (2)0.0251 (2)0.0209 (2)0.0009 (2)0.0003 (2)0.0016 (1)
O110.0240 (6)0.0345 (6)0.0504 (7)0.0020 (5)0.0059 (5)0.0106 (5)
O210.0417 (6)0.0374 (6)0.0219 (5)0.0049 (5)0.0032 (5)0.0011 (4)
O310.0220 (5)0.0404 (6)0.0307 (6)0.0049 (5)0.0035 (4)0.0020 (5)
O410.0392 (6)0.0308 (6)0.0243 (6)0.0089 (5)0.0031 (5)0.0015 (5)
P20.0209 (2)0.0270 (2)0.0210 (2)0.0007 (2)0.001 (2)0.0002 (2)
O120.0236 (6)0.0324 (6)0.0534 (8)0.0004 (5)0.0052 (5)0.0058 (5)
O220.0548 (8)0.0333 (6)0.0218 (6)0.0036 (5)0.0049 (5)0.0013 (5)
O320.0221 (5)0.0449 (7)0.0335 (6)0.0057 (5)0.0029 (4)0.0007 (5)
O420.0358 (6)0.0314 (6)0.0238 (5)0.0054 (5)0.0018 (4)0.0026 (4)
N10.0284 (7)0.0317 (8)0.0306 (8)0.0018 (6)0.0006 (7)0.0012 (6)
C110.0280 (9)0.0314 (9)0.0318 (9)0.0007 (7)0.0038 (7)0.0012 (7)
C210.0314 (9)0.0305 (9)0.043 (1)0.0001 (7)0.0000 (8)0.0005 (7)
C310.035 (1)0.0317 (9)0.048 (1)0.0015 (7)0.0022 (9)0.0022 (8)
C410.047 (1)0.0338 (9)0.043 (1)0.0045 (8)0.0009 (9)0.0014 (8)
C510.070 (2)0.034 (1)0.060 (1)0.002 (1)0.000 (1)0.0005 (9)
N20.0298 (7)0.0276 (7)0.0295 (8)0.0019 (6)0.0012 (7)0.0001 (6)
C120.0265 (8)0.0336 (9)0.0330 (9)0.0015 (7)0.0021 (7)0.0020 (7)
C220.0278 (9)0.0329 (9)0.044 (1)0.001 (7)0.0001 (8)0.0006 (8)
C320.0338 (9)0.0318 (9)0.048 (1)0.0027 (7)0.0018 (9)0.0019 (8)
C420.045 (1)0.0324 (9)0.044 (1)0.0023 (8)0.0012 (9)0.0011 (8)
C520.073 (2)0.034 (1)0.060 (1)0.003 (1)0.003 (1)0.002 (1)
Geometric parameters (Å, º) top
P1—O111.560 (1)O31—N2v2.816 (2)
P1—O211.504 (1)O41—N2vi2.857 (2)
P1—O311.498 (1)P2—O121.556 (1)
P1—O411.572 (1)P2—O221.570 (1)
O11—HO110.78 (2)P2—O321.495 (1)
O41—HO410.87 (2)P2—O421.514 (1)
N1—C111.488 (2)O12—HO120.75 (2)
C11—C211.514 (2)O22—HO220.96 (2)
C21—C311.519 (2)N2—C121.484 (2)
C31—C411.525 (3)C12—C221.511 (2)
C41—C511.526 (3)C22—C321.520 (2)
O11—O32i2.601 (2)C32—C421.523 (3)
O21—O22ii2.548 (2)C42—C521.527 (3)
O31—O122.591 (2)O22—N1vii3.004 (2)
O41—O42iii2.507 (1)O32—N1viii2.797 (2)
O21—N2iv2.859 (2)O42—N1ix2.762 (2)
O11—P1—O21110.51 (6)O12—P2—O22105.46 (6)
O11—P1—O31106.99 (6)O12—P2—O32107.31 (6)
O11—P1—O41107.05 (6)O12—P2—O42111.14 (6)
O21—P1—O31116.62 (6)O22—P2—O32111.26 (6)
O21—P1—O41105.33 (6)O22—P2—O42107.52 (6)
O31—P1—O41109.98 (6)O32—P2—O42113.87 (6)
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z; (vi) x+1/2, y1/2, z+1/2; (vii) x+2, y+1, z; (viii) x+2, y+1, z+1; (ix) x+3/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HD···AD—H···A
O11—HO11···O32i0.78 (2)2.600 (1)174 (2)
O41—HO41···O42iii0.87 (2)2.507 (1)177 (2)
O22—HO22···O21x0.96 (2)2.547 (2)171 (2)
O12—HO12···O310.75 (2)2.591 (1)172 (2)
N1—H1N1···O32viii0.88 (2)2.797 (2)170 (2)
N1—H2N1···O42xi0.91 (2)2.761 (2)166 (2)
N1—H3N1···O22vii0.82 (2)3.003 (2)156 (2)
N2—H1N2···O21iv0.85 (2)2.859 (2)162 (2)
N2—H2N2···O41xii0.87 (2)2.857 (2)162 (2)
N2—H3N2···O31v0.91 (2)2.815 (2)161 (2)
Symmetry codes: (i) x1, y, z; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z; (vii) x+2, y+1, z; (viii) x+2, y+1, z+1; (x) x+1/2, y+1/2, z1/2; (xi) x+3/2, y+1/2, z+1/2; (xii) x+1/2, y+1/2, z+1/2.
(C6ADP) top
Crystal data top
C6H16N+·H2O4PF(000) = 864
Mr = 199.19Dx = 1.338 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 50 reflections
a = 9.143 (1) Åθ = 5.6–22.8°
b = 29.637 (8) ŵ = 0.26 mm1
c = 7.299 (1) ÅT = 290 K
β = 90.86 (1)°Plate, colourless
V = 1977.7 (7) Å30.33 × 0.20 × 0.10 mm
Z = 8
Data collection top
Hilger & Watts
diffractometer
θmax = 25°
ω–2θ scansh = 1010
5446 measured reflectionsk = 3535
3452 independent reflectionsl = 08
2167 reflections with I > 3σ(I)3 standard reflections every 30 reflections
Rint = 0.060 intensity decay: 6.0%
Refinement top
Refinement on F0 constraints
Least-squares matrix: full with fixed elements per cycleAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.050w = (σ2(Fo) + 0.0001(Fo)2)-1
wR(F2) = 0.056(Δ/σ)max = 0.01
S = 1.71Δρmax = 0.46 e Å3
3452 reflectionsΔρmin = 0.54 e Å3
363 parametersExtinction correction: Becker & Coppens, 1974, type II
4 restraintsExtinction coefficient: 0.00017 (2)
Crystal data top
C6H16N+·H2O4PV = 1977.7 (7) Å3
Mr = 199.19Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.143 (1) ŵ = 0.26 mm1
b = 29.637 (8) ÅT = 290 K
c = 7.299 (1) Å0.33 × 0.20 × 0.10 mm
β = 90.86 (1)°
Data collection top
Hilger & Watts
diffractometer
Rint = 0.060
5446 measured reflections3 standard reflections every 30 reflections
3452 independent reflections intensity decay: 6.0%
2167 reflections with I > 3σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0504 restraints
wR(F2) = 0.056All H-atom parameters refined
S = 1.71Δρmax = 0.46 e Å3
3452 reflectionsΔρmin = 0.54 e Å3
363 parameters
Special details top

Refinement. The structure was refined as a twin. the domain fraction f of the minor domain: 0.040 (6) from measured intensities of 46 pairs of separated reflections: 0.066 (2)

The twinning matrix is given in _diffrn_reflns_transf_matrix items

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.08787 (7)0.30071 (2)0.25532 (9)0.0232 (2)
O110.0327 (2)0.33731 (6)0.2298 (3)0.0368 (7)
O210.1194 (2)0.29233 (6)0.4548 (2)0.0335 (6)
O310.2159 (2)0.31489 (6)0.1415 (2)0.0324 (6)
O410.0230 (2)0.25539 (6)0.1804 (3)0.0334 (6)
P20.58373 (7)0.29784 (2)0.26410 (9)0.0236 (2)
O120.4712 (2)0.33714 (6)0.2666 (3)0.0371 (7)
O220.6176 (2)0.28995 (7)0.0574 (2)0.0379 (7)
O320.7172 (2)0.31308 (7)0.3665 (2)0.0344 (6)
O420.5179 (2)0.25485 (6)0.3389 (2)0.0302 (6)
N10.1904 (3)0.69309 (9)0.2676 (4)0.0307 (8)
C110.1059 (3)0.65055 (9)0.2485 (4)0.0315 (9)
C210.2023 (3)0.60953 (9)0.2565 (5)0.035 (1)
C310.1128 (3)0.5666 (1)0.2502 (5)0.038 (1)
C410.2032 (4)0.5236 (1)0.2529 (5)0.038 (1)
C510.1132 (4)0.4807 (1)0.2502 (6)0.048 (1)
C610.2029 (6)0.4381 (1)0.2539 (6)0.058 (2)
N20.6999 (3)0.69255 (8)0.2263 (4)0.0306 (8)
C120.6110 (3)0.65082 (9)0.2444 (4)0.0316 (9)
C220.7048 (3)0.60921 (9)0.2425 (4)0.0334 (9)
C320.6133 (3)0.56635 (9)0.2489 (5)0.039 (1)
C420.7031 (4)0.5236 (1)0.2468 (5)0.039 (1)
C520.6126 (4)0.4806 (1)0.2489 (6)0.048 (1)
C620.7008 (6)0.4380 (1)0.2467 (6)0.060 (2)
H1N20.760 (3)0.691 (1)0.302 (4)0.036 (9)*
H2N20.642 (3)0.7182 (9)0.241 (3)0.022 (7)*
H3N20.741 (3)0.6918 (9)0.107 (4)0.042 (9)*
H1C120.564 (3)0.6557 (9)0.349 (4)0.034 (8)*
H2C120.540 (3)0.6499 (8)0.143 (4)0.029 (7)*
H1C220.777 (4)0.608 (1)0.114 (5)0.06 (1)*
H2C220.775 (3)0.6078 (8)0.344 (4)0.033 (7)*
H1C320.548 (4)0.567 (1)0.365 (5)0.06 (1)*
H2C320.553 (3)0.5672 (9)0.150 (4)0.041 (9)*
H1C420.755 (3)0.5232 (9)0.137 (5)0.040 (9)*
H2C420.769 (4)0.523 (1)0.350 (5)0.06 (1)*
H1C520.540 (4)0.482 (1)0.150 (5)0.06 (1)*
H2C520.549 (4)0.481 (1)0.360 (6)0.08 (1)*
H1C620.775 (5)0.437 (1)0.342 (6)0.09 (1)*
H2C620.639 (4)0.413 (1)0.242 (5)0.08 (1)*
H3C620.760 (4)0.437 (1)0.133 (6)0.08 (1)*
H1N10.233 (3)0.6935 (9)0.383 (4)0.036 (8)*
H2N10.128 (4)0.716 (1)0.255 (4)0.048 (9)*
H3N10.257 (4)0.692 (1)0.200 (4)0.04 (1)*
H2C110.050 (4)0.653 (1)0.137 (5)0.057 (9)*
H1C110.031 (4)0.651 (1)0.337 (5)0.05 (1)*
H1C210.269 (3)0.610 (1)0.162 (4)0.047 (9)*
H2C210.266 (4)0.610 (1)0.379 (5)0.06 (1)*
H1C310.052 (3)0.5656 (9)0.344 (4)0.035 (9)*
H2C310.058 (3)0.5663 (9)0.144 (4)0.035 (8)*
H1C410.270 (4)0.521 (1)0.157 (6)0.07 (1)*
H2C410.270 (3)0.5229 (9)0.371 (5)0.048 (9)*
H1C510.047 (4)0.483 (1)0.139 (5)0.07 (1)*
H2C510.059 (3)0.4819 (9)0.359 (4)0.030 (8)*
H1C610.262 (4)0.434 (1)0.364 (6)0.07 (1)*
H2C610.140 (5)0.416 (2)0.246 (6)0.09 (1)*
H3C610.259 (6)0.437 (2)0.154 (7)0.11 (2)*
HO110.117 (2)0.329 (1)0.257 (4)0.05 (1)*
HO410.017 (3)0.253 (1)0.065 (1)0.06 (1)*
HO120.391 (2)0.327 (1)0.224 (4)0.05 (1)*
HO220.606 (3)0.2624 (4)0.027 (4)0.041 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0220 (3)0.0267 (4)0.0209 (3)0.0013 (3)0.0023 (3)0.0017 (3)
O110.026 (1)0.034 (1)0.051 (1)0.0021 (9)0.0056 (9)0.0087 (9)
O210.045 (1)0.036 (1)0.020 (1)0.0047 (9)0.0017 (8)0.0009 (8)
O310.0228 (9)0.045 (1)0.029 (1)0.0075 (8)0.0054 (7)0.0020 (8)
O410.043 (1)0.034 (1)0.022 (1)0.0113 (9)0.0039 (9)0.0011 (9)
P20.0216 (3)0.0269 (4)0.0222 (3)0.0007 (3)0.0002 (3)0.0001 (3)
O120.023 (1)0.034 (1)0.054 (1)0.0022 (8)0.0009 (9)0.0070 (9)
O220.056 (1)0.036 (1)0.021 (1)0.009 (1)0.0063 (9)0.0007 (9)
O320.0227 (9)0.048 (1)0.032 (1)0.0034 (8)0.0015 (8)0.0003 (9)
O420.036 (1)0.034 (1)0.021 (1)0.0080 (8)0.0019 (8)0.0031 (8)
N10.029 (1)0.030 (1)0.033 (2)0.003 (1)0.003 (1)0.003 (1)
C110.027 (2)0.030 (1)0.037 (2)0.001 (1)0.002 (1)0.005 (1)
C210.033 (2)0.029 (2)0.044 (2)0.001 (1)0.004 (2)0.001 (1)
C310.039 (2)0.033 (2)0.042 (2)0.004 (1)0.000 (2)0.001 (1)
C410.043 (2)0.031 (2)0.041 (2)0.000 (1)0.001 (2)0.004 (1)
C510.062 (2)0.037 (2)0.044 (2)0.007 (2)0.006 (2)0.002 (2)
C610.094 (3)0.031 (2)0.051 (3)0.001 (2)0.003 (3)0.003 (2)
N20.031 (1)0.031 (1)0.030 (1)0.005 (1)0.001 (1)0.002 (1)
C120.028 (2)0.034 (2)0.033 (2)0.004 (1)0.006 (1)0.003 (1)
C220.031 (2)0.028 (2)0.040 (2)0.000 (1)0.001 (1)0.001 (1)
C320.040 (2)0.030 (2)0.047 (2)0.002 (1)0.001 (2)0.002 (1)
C420.050 (2)0.031 (2)0.036 (2)0.001 (1)0.005 (2)0.001 (1)
C520.060 (2)0.032 (2)0.052 (2)0.010 (2)0.002 (2)0.002 (2)
C620.094 (3)0.031 (2)0.054 (3)0.008 (2)0.007 (3)0.001 (2)
Geometric parameters (Å, º) top
P1—O111.556 (3)C51—C611.505 (6)
P1—O211.501 (3)N12—C121.486 (4)
P1—O311.505 (3)C12—C221.501 (4)
P1—O411.563 (3)C22—C321.523 (4)
O11—HO110.84 (2)C32—C421.509 (5)
O41—HO410.85 (1)C42—C521.521 (5)
P2—O121.554 (2)C52—C621.495 (6)
P2—O221.563 (2)O11—O32i2.610 (3)
P2—O321.492 (2)O21—O22ii2.550 (3)
P2—O421.515 (2)O31—O122.579 (3)
O12—HO120.85 (2)O41—O42iii2.511 (3)
O22—HO220.85 (1)O21—N2iv2.870 (3)
N11—C111.484 (4)O31—N2v2.813 (3)
C11—C211.501 (4)O41—N2vi2.850 (3)
C21—C311.514 (5)O22—N1v3.014 (3)
C31—C411.519 (5)O32—N1iv2.796 (3)
C41—C511.515 (5)O42—N1vi2.746 (3)
O11—P1—O21110.91 (11)O12—P2—O22105.34 (11)
O11—P1—O31107.13 (11)O12—P2—O32107.69 (11)
O11—P1—O41107.01 (10)O12—P2—O42111.07 (10)
O21—P1—O31116.25 (10)O22—P2—O32110.89 (11)
O21—P1—O41105.27 (10)O22—P2—O42107.93 (10)
O31—P1—O41109.93 (10)O32—P2—O42113.62 (10)
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z; (vi) x+1/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HD···AD—H···A
O11—HO11···O32i0.84 (2)2.610 (3)167 (3)
O41—HO41···O42iii0.85 (1)2.511 (3)174 (3)
O22—HO22···O21vii0.85 (1)2.551 (3)168 (3)
O12—HO12···O310.85 (2)2.580 (3)172 (3)
N1—H1N1···O32iv0.92 (3)2.796 (3)167 (3)
N1—H2N1···O42viii0.88 (3)2.746 (3)163 (3)
N1—H3N1···O22v0.79 (3)3.014 (3)155 (3)
N2—H1N2···O21iv0.78 (3)2.870 (3)159 (3)
N2—H2N2···O41viii0.93 (3)2.850 (3)158 (2)
N2—H3N2···O31v0.95 (4)2.813 (3)168 (3)
Symmetry codes: (i) x1, y, z; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z; (vii) x+1/2, y+1/2, z1/2; (viii) x+1/2, y+1/2, z+1/2.
(C9ADP) top
Crystal data top
C9H22N+·H2O4PF(000) = 1056
Mr = 241.27Dx = 1.284 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 50 reflections
a = 9.138 (3) Åθ = 4.3–18.0°
b = 36.984 (9) ŵ = 0.22 mm1
c = 7.383 (2) ÅT = 290 K
β = 90.88 (2)°Plate, colourless
V = 2495 (1) Å30.33 × 0.21 × 0.10 mm
Z = 8
Data collection top
Hilger & Watts
diffractometer
Rint = 0.073
ω–2θ scansθmax = 26°
Absorption correction: gaussian
AGNOST C, Templeton & Templeton (1978)
h = 011
Tmin = 0.942, Tmax = 0.978k = 4545
13662 measured reflectionsl = 99
4906 independent reflections3 standard reflections every 30 reflections
2948 reflections with I > 3σ(I) intensity decay: 7.0%
Refinement top
Refinement on F3 constraints
Least-squares matrix: full with fixed elements per cycleAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.053w = (σ2(Fo) + 0.0001(Fo)2)-1
wR(F2) = 0.058(Δ/σ)max = 0.01
S = 1.91Δρmax = 0.66 e Å3
4906 reflectionsΔρmin = 0.59 e Å3
466 parametersExtinction correction: Becker & Coppens, 1974, type II
2 restraintsExtinction coefficient: 0.00028 (3)
Crystal data top
C9H22N+·H2O4PV = 2495 (1) Å3
Mr = 241.27Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.138 (3) ŵ = 0.22 mm1
b = 36.984 (9) ÅT = 290 K
c = 7.383 (2) Å0.33 × 0.21 × 0.10 mm
β = 90.88 (2)°
Data collection top
Hilger & Watts
diffractometer
2948 reflections with I > 3σ(I)
Absorption correction: gaussian
AGNOST C, Templeton & Templeton (1978)
Rint = 0.073
Tmin = 0.942, Tmax = 0.9783 standard reflections every 30 reflections
13662 measured reflections intensity decay: 7.0%
4906 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.058All H-atom parameters refined
S = 1.91Δρmax = 0.66 e Å3
4906 reflectionsΔρmin = 0.59 e Å3
466 parameters
Special details top

Refinement. The structure was refined as a twin; the reflections hkl;h=2n and hkl;h=2n+1 were refined on different scales, respectively. the domain fraction f of the minor domain: 0.047 (5) from measured intensities of 26 pairs of separated reflections: 0.037 (5)

The twinning matrix is given in _diffrn_reflns_transf_matrix items

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.06381 (7)0.29018 (2)0.25460 (7)0.0223 (2)Uani
O110.0570 (2)0.31936 (5)0.2272 (3)0.0353 (6)Uani
O210.0935 (2)0.28355 (4)0.4522 (2)0.0334 (5)Uani
O310.1915 (2)0.30118 (4)0.1433 (2)0.0295 (5)Uani
O410.0019 (2)0.25370 (4)0.1801 (2)0.0299 (5)Uani
P20.55976 (7)0.28770 (2)0.26507 (7)0.0222 (2)Uani
O120.4483 (2)0.31938 (4)0.2715 (2)0.0347 (6)Uani
O220.5914 (2)0.28178 (5)0.0598 (2)0.0384 (6)Uani
O320.6946 (2)0.29976 (4)0.3648 (2)0.0318 (5)Uani
O420.4944 (2)0.25338 (4)0.3385 (2)0.0304 (5)Uani
N10.2188 (3)0.70564 (6)0.2699 (3)0.0307 (7)Uani
C110.1385 (3)0.67063 (6)0.2483 (3)0.0293 (8)Uani
C210.2380 (3)0.63869 (6)0.2569 (4)0.0327 (8)Uani
C310.1528 (3)0.60349 (7)0.2494 (4)0.0354 (9)Uani
C410.2475 (3)0.56978 (6)0.2528 (4)0.0323 (8)Uani
C510.1588 (3)0.53509 (6)0.2505 (4)0.0341 (9)Uani
C610.2521 (3)0.50091 (6)0.2521 (3)0.0328 (8)Uani
C710.1638 (3)0.46631 (6)0.2525 (4)0.0346 (9)Uani
C810.2563 (4)0.43249 (7)0.2546 (4)0.0388 (9)Uani
C910.1660 (5)0.39808 (8)0.2564 (5)0.053 (1)Uani
N20.7297 (3)0.70470 (6)0.2256 (3)0.0291 (7)Uani
C120.6438 (3)0.67100 (6)0.2436 (4)0.0302 (8)Uani
C220.7400 (3)0.63820 (6)0.2408 (4)0.0311 (8)Uani
C320.6536 (3)0.60324 (7)0.2478 (4)0.0349 (9)Uani
C420.7471 (3)0.56961 (6)0.2471 (4)0.0326 (8)Uani
C520.6589 (3)0.53493 (7)0.2467 (4)0.0347 (9)Uani
C620.7518 (3)0.50082 (6)0.2487 (4)0.0328 (8)Uani
C720.6638 (3)0.46617 (7)0.2461 (4)0.0353 (9)Uani
C820.7556 (4)0.43219 (7)0.2476 (4)0.0396 (9)Uani
C920.6655 (4)0.39767 (8)0.2429 (5)0.052 (1)Uani
H1N20.807 (2)0.7064 (9)0.300 (3)0.08 (1)Uiso
H2N20.675 (3)0.7212 (7)0.233 (3)0.031 (7)Uiso
H3N20.770 (3)0.7041 (7)0.109 (4)0.053 (8)Uiso
H2C120.576 (3)0.6700 (6)0.149 (3)0.025 (6)Uiso
H1C120.591 (3)0.6746 (7)0.354 (3)0.045 (7)Uiso
H1C220.797 (3)0.6393 (8)0.139 (4)0.059 (9)Uiso
H2C220.811 (3)0.6397 (7)0.350 (3)0.041 (7)Uiso
H1C320.594 (3)0.6045 (7)0.353 (3)0.046 (8)Uiso
H2C320.592 (2)0.6022 (6)0.151 (3)0.032 (7)Uiso
H1C420.813 (3)0.5707 (7)0.135 (3)0.044 (7)Uiso
H2C420.815 (3)0.5705 (7)0.349 (4)0.047 (8)Uiso
H1C520.597 (3)0.5353 (7)0.140 (4)0.042 (8)Uiso
H2C520.597 (3)0.5343 (7)0.353 (4)0.046 (8)Uiso
H1C620.814 (3)0.5028 (6)0.148 (3)0.028 (6)Uiso
H2C620.825 (3)0.5019 (7)0.358 (4)0.046 (8)Uiso
H1C720.598 (3)0.4663 (7)0.139 (3)0.037 (7)Uiso
H2C720.600 (3)0.4661 (6)0.352 (3)0.030 (6)Uiso
H1C820.814 (3)0.4328 (7)0.142 (4)0.045 (8)Uiso
H2C820.822 (3)0.4329 (7)0.358 (4)0.040 (7)Uiso
H1C920.603 (3)0.3956 (7)0.349 (4)0.052 (8)Uiso
H2C920.730 (4)0.377 (1)0.238 (4)0.08 (1)Uiso
H3C920.607 (4)0.3951 (8)0.134 (4)0.06 (1)Uiso
H1N10.253 (3)0.7068 (8)0.373 (4)0.053 (9)Uiso
H2N10.153 (4)0.7257 (9)0.245 (4)0.07 (1)Uiso
H3N10.285 (4)0.7064 (9)0.190 (4)0.07 (1)Uiso
H1C110.072 (3)0.6696 (7)0.341 (3)0.047 (8)Uiso
H2C110.096 (3)0.6728 (6)0.122 (3)0.035 (7)Uiso
H2C210.288 (3)0.6402 (8)0.358 (4)0.06 (1)Uiso
H1C210.306 (3)0.6382 (7)0.156 (3)0.047 (8)Uiso
H1C310.082 (3)0.6033 (7)0.343 (4)0.051 (8)Uiso
H2C310.078 (4)0.6026 (8)0.144 (4)0.07 (1)Uiso
H2C410.307 (3)0.5701 (6)0.355 (3)0.022 (6)Uiso
H1C410.308 (3)0.5702 (6)0.152 (3)0.031 (7)Uiso
H1C510.094 (3)0.5350 (7)0.143 (4)0.049 (8)Uiso
H2C510.092 (3)0.5340 (7)0.360 (4)0.051 (8)Uiso
H1C610.320 (3)0.5006 (6)0.141 (3)0.035 (6)Uiso
H2C610.317 (3)0.5029 (6)0.347 (3)0.028 (6)Uiso
H1C710.099 (3)0.4649 (7)0.143 (4)0.051 (8)Uiso
H2C710.095 (3)0.4650 (7)0.367 (4)0.048 (8)Uiso
H1C810.320 (3)0.4309 (6)0.145 (3)0.035 (7)Uiso
H2C810.326 (3)0.4338 (6)0.357 (3)0.031 (7)Uiso
H1C910.098 (4)0.3962 (9)0.370 (5)0.09 (1)Uiso
H2C910.229 (4)0.378 (1)0.254 (5)0.09 (1)Uiso
H3C910.097 (4)0.3963 (8)0.154 (4)0.06 (1)Uiso
HO110.123 (5)0.317 (1)0.286 (5)0.10 (2)Uiso
HO410.003 (4)0.2519 (9)0.066 (4)0.08 (1)Uiso
HO120.371 (2)0.3133 (6)0.247 (3)0.011 (6)Uiso
HO220.581 (3)0.2610 (8)0.034 (3)0.045 (8)Uiso
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0211 (3)0.0239 (3)0.0220 (3)0.0016 (3)0.0001 (2)0.0017 (2)
O110.027 (1)0.0293 (9)0.050 (1)0.0034 (8)0.0027 (8)0.0097 (7)
O210.047 (1)0.0315 (9)0.0216 (7)0.0024 (8)0.0009 (7)0.0002 (6)
O310.0256 (9)0.035 (1)0.0282 (8)0.0043 (7)0.0037 (6)0.0024 (6)
O410.041 (1)0.0256 (8)0.0236 (8)0.0081 (7)0.0010 (7)0.0013 (6)
P20.0215 (3)0.0230 (3)0.0221 (3)0.0007 (3)0.0013 (2)0.0005 (2)
O120.022 (1)0.027 (1)0.055 (1)0.0002 (8)0.0040 (8)0.0067 (7)
O220.062 (1)0.029 (1)0.0245 (8)0.0097 (9)0.0063 (7)0.0005 (7)
O320.0241 (8)0.041 (1)0.0304 (8)0.0046 (7)0.0034 (6)0.0020 (6)
O420.0403 (9)0.0273 (8)0.0236 (8)0.0056 (7)0.0005 (6)0.0014 (6)
N10.031 (1)0.024 (1)0.037 (1)0.0016 (9)0.001 (1)0.0020 (9)
C110.027 (1)0.025 (1)0.035 (1)0.004 (1)0.002 (1)0.000 (1)
C210.030 (1)0.024 (1)0.044 (2)0.001 (1)0.002 (1)0.002 (1)
C310.034 (2)0.024 (1)0.048 (2)0.004 (1)0.000 (1)0.001 (1)
C410.032 (1)0.029 (1)0.036 (1)0.003 (1)0.001 (1)0.001 (1)
C510.040 (2)0.022 (1)0.040 (2)0.002 (1)0.002 (1)0.000 (1)
C610.035 (1)0.028 (1)0.035 (1)0.004 (1)0.003 (1)0.003 (1)
C710.040 (2)0.023 (1)0.041 (2)0.000 (1)0.000 (1)0.001 (1)
C810.045 (2)0.033 (1)0.038 (1)0.004 (1)0.001 (1)0.001 (1)
C910.075 (3)0.027 (2)0.058 (2)0.005 (2)0.002 (2)0.003 (1)
N20.031 (1)0.023 (1)0.034 (1)0.003 (1)0.000 (1)0.0020 (8)
C120.027 (1)0.027 (1)0.037 (1)0.001 (1)0.003 (1)0.001 (1)
C220.029 (1)0.025 (1)0.040 (1)0.000 (1)0.003 (1)0.001 (1)
C320.032 (2)0.029 (1)0.044 (2)0.003 (1)0.002 (1)0.001 (1)
C420.035 (1)0.026 (1)0.037 (1)0.003 (1)0.003 (1)0.000 (1)
C520.036 (2)0.027 (1)0.041 (2)0.003 (1)0.002 (1)0.003 (1)
C620.036 (1)0.025 (1)0.037 (1)0.002 (1)0.001 (1)0.001 (1)
C720.042 (2)0.027 (1)0.037 (1)0.004 (1)0.001 (1)0.002 (1)
C820.051 (2)0.030 (1)0.037 (1)0.001 (1)0.000 (1)0.000 (1)
C920.071 (2)0.027 (2)0.056 (2)0.001 (2)0.004 (2)0.003 (1)
Geometric parameters (Å, º) top
P1—O111.555 (2)C71—H2C711.06 (3)
P1—O211.500 (1)C81—H1C811.00 (2)
P1—O311.493 (2)C81—H2C810.98 (3)
P1—O411.573 (2)C91—H1C911.05 (4)
O11—HO110.75 (4)C91—H2C910.95 (4)
O41—HO410.85 (3)C91—H3C910.98 (3)
P2—O121.553 (2)N2—C121.480 (3)
P2—O221.562 (2)C12—C221.499 (3)
P2—O321.494 (2)C22—C321.517 (4)
P2—O421.508 (2)C32—C421.509 (4)
O12—HO120.76 (2)C42—C521.515 (4)
O22—HO220.80 (3)C52—C621.521 (4)
N1—C111.496 (3)C62—C721.513 (4)
C11—C211.492 (3)C72—C821.511 (4)
C21—C311.518 (4)C82—C921.519 (4)
C31—C411.518 (4)N2—H1N20.89 (2)
C41—C511.518 (4)N2—H2N20.79 (3)
C51—C611.525 (4)N2—H3N20.94 (3)
C61—C711.513 (4)C12—H2C120.93 (2)
C71—C811.510 (4)C12—H1C120.97 (3)
C81—C911.517 (4)C22—H1C220.92 (3)
N1—H1N10.82 (3)C22—H2C221.03 (3)
N1—H2N10.97 (3)C32—H1C320.96 (2)
N1—H3N10.85 (3)C32—H2C320.91 (2)
C11—H1C110.93 (3)C42—H1C421.03 (3)
C11—H2C111.00 (2)C42—H2C420.97 (3)
C21—H2C210.87 (3)C52—H1C520.96 (3)
C21—H1C210.98 (3)C52—H2C520.97 (3)
C31—H1C310.95 (3)C62—H1C620.94 (2)
C31—H2C311.03 (3)C62—H2C621.04 (3)
C41—H2C410.92 (2)C72—H1C720.98 (3)
C41—H1C410.93 (2)C72—H2C720.98 (2)
C51—H1C510.99 (3)C82—H1C820.95 (3)
C51—H2C511.02 (3)C82—H2C821.01 (3)
C61—H1C611.04 (2)C92—H1C920.98 (3)
C61—H2C610.92 (2)C92—H2C920.97 (4)
C71—H1C711.00 (3)C92—H3C920.96 (3)
O11—P1—O21110.95 (10)O12—P2—O22105.45 (10)
O11—P1—O31107.37 (9)O12—P2—O32107.22 (10)
O11—P1—O41106.45 (9)O12—P2—O42111.13 (10)
O21—P1—O31116.63 (9)O22—P2—O32110.89 (10)
O21—P1—O41105.22 (9)O22—P2—O42108.11 (9)
O31—P1—O41109.78 (9)O32—P2—O42113.74 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HD···AD—H···A
O11—HO11···O32i0.75 (4)2.604 (2)160 (4)
O41—HO41···O42ii0.85 (3)2.535 (2)178 (4)
O22—HO22···O21iii0.80 (3)2.544 (2)167 (3)
O12—HO12···O310.76 (2)2.606 (2)169 (2)
N1iv—H1N1···O32v0.82 (3)2.806 (3)167 (3)
N1vi—H2N1···O42vii0.97 (3)2.739 (3)164 (3)
N1—H3N1···O220.85 (3)3.047 (3)162 (3)
N2—H1N2···O21v0.89 (2)2.888 (3)153 (2)
N2—H2N2···O41vii0.79 (3)2.854 (3)161 (2)
N2—H3N2···O31viii0.94 (3)2.837 (3)167 (3)
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z+1; (vi) x, y1, z; (vii) x+1/2, y+1/2, z+1/2; (viii) x+1, y+1, z.

Experimental details

(C5ADP)(C6ADP)(C9ADP)
Crystal data
Chemical formulaC5H14N+·H2O4PC6H16N+·H2O4PC9H22N+·H2O4P
Mr185.16199.19241.27
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)290290290
a, b, c (Å)9.149 (2), 27.081 (3), 7.290 (1)9.143 (1), 29.637 (8), 7.299 (1)9.138 (3), 36.984 (9), 7.383 (2)
β (°) 90.82 (1) 90.86 (1) 90.88 (2)
V3)1806.2 (5)1977.7 (7)2495 (1)
Z888
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.280.260.22
Crystal size (mm)0.56 × 0.32 × 0.150.33 × 0.20 × 0.100.33 × 0.21 × 0.10
Data collection
DiffractometerEnraf-Nonius CAD-4-MACHIII-PC
diffractometer
Hilger & Watts
diffractometer
Hilger & Watts
diffractometer
Absorption correctionGaussian
AGNOST C, Templeton & Templeton (1978)
Tmin, Tmax0.942, 0.978
No. of measured, independent and
observed [I > 3σ(I)] reflections
3418, 3167, 2417 5446, 3452, 2167 13662, 4906, 2948
Rint0.0340.0600.073
(sin θ/λ)max1)0.5950.5950.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.055, 2.58 0.050, 0.056, 1.71 0.053, 0.058, 1.91
No. of reflections316734524906
No. of parameters329363466
No. of restraints?42
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.33, 0.340.46, 0.540.66, 0.59

Computer programs: Enraf-Nonius Software, HW, Petříček, 1998, JANA98, Petříček & Dušek, 1998, SHELXS86, Sheldrick, 1986, PICTUR (Dušek, 1993).

Selected bond lengths (Å) for (C5ADP) top
P1—O111.560 (1)O31—N2v2.816 (2)
P1—O211.504 (1)O41—N2vi2.857 (2)
P1—O311.498 (1)P2—O121.556 (1)
P1—O411.572 (1)P2—O221.570 (1)
O11—HO110.78 (2)P2—O321.495 (1)
O41—HO410.87 (2)P2—O421.514 (1)
N1—C111.488 (2)O12—HO120.75 (2)
C11—C211.514 (2)O22—HO220.96 (2)
C21—C311.519 (2)N2—C121.484 (2)
C31—C411.525 (3)C12—C221.511 (2)
C41—C511.526 (3)C22—C321.520 (2)
O11—O32i2.601 (2)C32—C421.523 (3)
O21—O22ii2.548 (2)C42—C521.527 (3)
O31—O122.591 (2)O22—N1vii3.004 (2)
O41—O42iii2.507 (1)O32—N1viii2.797 (2)
O21—N2iv2.859 (2)O42—N1ix2.762 (2)
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z; (vi) x+1/2, y1/2, z+1/2; (vii) x+2, y+1, z; (viii) x+2, y+1, z+1; (ix) x+3/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (C5ADP) top
D—H···AD—HD···AD—H···A
O11—HO11···O32i0.78 (2)2.600 (1)174 (2)
O41—HO41···O42iii0.87 (2)2.507 (1)177 (2)
O22—HO22···O21x0.96 (2)2.547 (2)171 (2)
O12—HO12···O310.75 (2)2.591 (1)172 (2)
N1—H1N1···O32viii0.88 (2)2.797 (2)170 (2)
N1—H2N1···O42xi0.91 (2)2.761 (2)166 (2)
N1—H3N1···O22vii0.82 (2)3.003 (2)156 (2)
N2—H1N2···O21iv0.85 (2)2.859 (2)162 (2)
N2—H2N2···O41xii0.87 (2)2.857 (2)162 (2)
N2—H3N2···O31v0.91 (2)2.815 (2)161 (2)
Symmetry codes: (i) x1, y, z; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z; (vii) x+2, y+1, z; (viii) x+2, y+1, z+1; (x) x+1/2, y+1/2, z1/2; (xi) x+3/2, y+1/2, z+1/2; (xii) x+1/2, y+1/2, z+1/2.
Selected bond lengths (Å) for (C6ADP) top
P1—O111.556 (3)N12—C121.486 (4)
P1—O211.501 (3)C12—C221.501 (4)
P1—O311.505 (3)C22—C321.523 (4)
P1—O411.563 (3)C32—C421.509 (5)
O11—HO110.84 (2)C42—C521.521 (5)
O41—HO410.85 (1)C52—C621.495 (6)
P2—O121.554 (2)O11—O32i2.610 (3)
P2—O221.563 (2)O21—O22ii2.550 (3)
P2—O321.492 (2)O31—O122.579 (3)
P2—O421.515 (2)O41—O42iii2.511 (3)
N11—C111.484 (4)O21—N2iv2.870 (3)
C11—C211.501 (4)O31—N2v2.813 (3)
C21—C311.514 (5)O41—N2vi2.850 (3)
C31—C411.519 (5)O22—N1v3.014 (3)
C41—C511.515 (5)O32—N1iv2.796 (3)
C51—C611.505 (6)O42—N1vi2.746 (3)
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z; (vi) x+1/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (C6ADP) top
D—H···AD—HD···AD—H···A
O11—HO11···O32i0.84 (2)2.610 (3)167 (3)
O41—HO41···O42iii0.85 (1)2.511 (3)174 (3)
O22—HO22···O21vii0.85 (1)2.551 (3)168 (3)
O12—HO12···O310.85 (2)2.580 (3)172 (3)
N1—H1N1···O32iv0.92 (3)2.796 (3)167 (3)
N1—H2N1···O42viii0.88 (3)2.746 (3)163 (3)
N1—H3N1···O22v0.79 (3)3.014 (3)155 (3)
N2—H1N2···O21iv0.78 (3)2.870 (3)159 (3)
N2—H2N2···O41viii0.93 (3)2.850 (3)158 (2)
N2—H3N2···O31v0.95 (4)2.813 (3)168 (3)
Symmetry codes: (i) x1, y, z; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z; (vii) x+1/2, y+1/2, z1/2; (viii) x+1/2, y+1/2, z+1/2.
Selected bond lengths (Å) for (C9ADP) top
P1—O111.555 (2)O22—HO220.80 (3)
P1—O211.500 (1)N1—C111.496 (3)
P1—O311.493 (2)C11—C211.492 (3)
P1—O411.573 (2)C21—C311.518 (4)
O11—HO110.75 (4)C31—C411.518 (4)
O41—HO410.85 (3)C41—C511.518 (4)
P2—O121.553 (2)C51—C611.525 (4)
P2—O221.562 (2)C61—C711.513 (4)
P2—O321.494 (2)C71—C811.510 (4)
P2—O421.508 (2)C81—C911.517 (4)
O12—HO120.76 (2)
Hydrogen-bond geometry (Å, º) for (C9ADP) top
D—H···AD—HD···AD—H···A
O11—HO11···O32i0.75 (4)2.604 (2)160 (4)
O41—HO41···O42ii0.85 (3)2.535 (2)178 (4)
O22—HO22···O21iii0.80 (3)2.544 (2)167 (3)
O12—HO12···O310.76 (2)2.606 (2)169 (2)
N1iv—H1N1···O32v0.82 (3)2.806 (3)167 (3)
N1vi—H2N1···O42vii0.97 (3)2.739 (3)164 (3)
N1—H3N1···O220.85 (3)3.047 (3)162 (3)
N2—H1N2···O21v0.89 (2)2.888 (3)153 (2)
N2—H2N2···O41vii0.79 (3)2.854 (3)161 (2)
N2—H3N2···O31viii0.94 (3)2.837 (3)167 (3)
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1, z+1; (vi) x, y1, z; (vii) x+1/2, y+1/2, z+1/2; (viii) x+1, y+1, z.
 

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