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
CCDC references: 153348; 153349; 153350
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
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.
Crystal data top
C5H14N+·H2O4P− | F(000) = 800 |
Mr = 185.16 | Dx = 1.361 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 9.149 (2) Å | θ = 9–15° |
b = 27.081 (3) Å | µ = 0.28 mm−1 |
c = 7.290 (1) Å | T = 290 K |
β = 90.82 (1)° | Plate, colourless |
V = 1806.2 (5) Å3 | 0.56 × 0.32 × 0.15 mm |
Z = 8 | |
Data collection top
Enraf-Nonius CAD-4-MACHIII-PC diffractometer | θmax = 25° |
ω–2θ scans | h = −10→10 |
3418 measured reflections | k = 0→32 |
3167 independent reflections | l = 0→8 |
2417 reflections with I > 3σ(I) | 3 standard reflections every 3600 min |
Rint = 0.034 | intensity decay: 2.2% |
Refinement top
Refinement on F | All H-atom parameters refined |
Least-squares matrix: full with fixed elements per cycle | w = (σ2(Fo) + 0.0001(Fo)2)-1 |
R[F2 > 2σ(F2)] = 0.040 | (Δ/σ)max = 0.01 |
wR(F2) = 0.055 | Δρmax = 0.33 e Å−3 |
S = 2.58 | Δρmin = −0.34 e Å−3 |
3167 reflections | Extinction correction: Becker & Coppens, 1974, type II |
329 parameters | Extinction coefficient: 0.00030 (4) |
0 constraints | |
Crystal data top
C5H14N+·H2O4P− | V = 1806.2 (5) Å3 |
Mr = 185.16 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.149 (2) Å | µ = 0.28 mm−1 |
b = 27.081 (3) Å | T = 290 K |
c = 7.290 (1) Å | 0.56 × 0.32 × 0.15 mm |
β = 90.82 (1)° | |
Data collection top
Enraf-Nonius CAD-4-MACHIII-PC diffractometer | Rint = 0.034 |
3418 measured reflections | 3 standard reflections every 3600 min |
3167 independent reflections | intensity decay: 2.2% |
2417 reflections with I > 3σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 329 parameters |
wR(F2) = 0.055 | All H-atom parameters refined |
S = 2.58 | Δρmax = 0.33 e Å−3 |
3167 reflections | Δρmin = −0.34 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
P1 | 0.31308 (4) | 0.30565 (1) | 0.25595 (5) | 0.0222 (1) | |
O11 | 0.1925 (1) | 0.34584 (4) | 0.2291 (2) | 0.0362 (4) | |
O21 | 0.3426 (1) | 0.29679 (4) | 0.4567 (1) | 0.0337 (4) | |
O31 | 0.4408 (1) | 0.32108 (4) | 0.1431 (1) | 0.0310 (3) | |
O41 | 0.2482 (1) | 0.25574 (4) | 0.1807 (1) | 0.0314 (3) | |
P2 | 0.80901 (4) | 0.30250 (1) | 0.26376 (5) | 0.0230 (1) | |
O12 | 0.6972 (1) | 0.34574 (4) | 0.2676 (2) | 0.0365 (4) | |
O22 | 0.8409 (1) | 0.29344 (4) | 0.0554 (1) | 0.0366 (4) | |
O32 | 0.9432 (1) | 0.31934 (4) | 0.3649 (1) | 0.0335 (3) | |
O42 | 0.7432 (1) | 0.25554 (4) | 0.3394 (1) | 0.0304 (3) | |
N1 | 0.9668 (2) | 0.68778 (5) | 0.2677 (2) | 0.0302 (4) | |
C11 | 0.8861 (2) | 0.64032 (6) | 0.2487 (2) | 0.0304 (5) | |
C21 | 0.9888 (2) | 0.59645 (6) | 0.2543 (2) | 0.0350 (5) | |
C31 | 0.9045 (2) | 0.54815 (6) | 0.2472 (3) | 0.0382 (6) | |
C41 | 1.0027 (2) | 0.50263 (6) | 0.2495 (3) | 0.0415 (6) | |
C51 | 0.9156 (3) | 0.45457 (8) | 0.2453 (3) | 0.0546 (8) | |
H1N1 | 1.002 (2) | 0.6887 (7) | 0.381 (3) | 0.052 (6)* | |
H2N1 | 0.903 (2) | 0.7131 (6) | 0.249 (2) | 0.026 (4)* | |
H3N1 | 1.035 (2) | 0.6871 (7) | 0.197 (3) | 0.045 (6)* | |
H1C11 | 0.818 (2) | 0.6389 (6) | 0.345 (2) | 0.041 (5)* | |
H2C11 | 0.840 (2) | 0.6410 (6) | 0.136 (2) | 0.032 (4)* | |
H2C21 | 1.050 (2) | 0.5978 (6) | 0.365 (2) | 0.046 (5)* | |
H1C21 | 1.065 (2) | 0.5984 (6) | 0.151 (2) | 0.048 (5)* | |
H1C31 | 0.835 (2) | 0.5493 (6) | 0.349 (2) | 0.040 (5)* | |
H2C31 | 0.843 (2) | 0.5482 (6) | 0.152 (2) | 0.044 (5)* | |
H2C41 | 1.067 (2) | 0.5063 (6) | 0.358 (2) | 0.033 (4)* | |
H1C41 | 1.071 (2) | 0.5068 (6) | 0.143 (2) | 0.039 (5)* | |
H1C51 | 0.851 (2) | 0.4546 (8) | 0.346 (3) | 0.070 (7)* | |
H2C51 | 0.993 (3) | 0.4289 (9) | 0.246 (3) | 0.084 (8)* | |
H3C51 | 0.850 (2) | 0.4566 (8) | 0.141 (3) | 0.070 (7)* | |
N2 | 0.4762 (2) | 0.68722 (5) | 0.2260 (2) | 0.0290 (4) | |
C12 | 0.3915 (2) | 0.64080 (6) | 0.2442 (2) | 0.0310 (5) | |
C22 | 0.4908 (2) | 0.59622 (6) | 0.2442 (2) | 0.0348 (5) | |
C32 | 0.4042 (2) | 0.54835 (6) | 0.2504 (3) | 0.0377 (6) | |
C42 | 0.5012 (2) | 0.50265 (6) | 0.2518 (3) | 0.0405 (6) | |
C52 | 0.4125 (3) | 0.45490 (8) | 0.2531 (3) | 0.0556 (8) | |
H2N2 | 0.418 (2) | 0.7123 (6) | 0.237 (2) | 0.017 (4)* | |
H1N2 | 0.541 (2) | 0.6870 (7) | 0.310 (3) | 0.058 (6)* | |
H3n2 | 0.523 (2) | 0.6867 (7) | 0.117 (3) | 0.052 (6)* | |
H2C12 | 0.341 (2) | 0.6423 (6) | 0.352 (2) | 0.046 (5)* | |
H1C12 | 0.325 (2) | 0.6406 (6) | 0.146 (2) | 0.046 (5)* | |
H2C22 | 0.564 (2) | 0.5983 (6) | 0.348 (2) | 0.050 (5)* | |
H1C22 | 0.561 (2) | 0.5978 (6) | 0.145 (2) | 0.045 (5)* | |
H1C32 | 0.338 (2) | 0.5488 (6) | 0.353 (2) | 0.036 (4)* | |
H2C32 | 0.340 (2) | 0.5481 (6) | 0.156 (2) | 0.042 (5)* | |
H2C42 | 0.573 (2) | 0.5070 (6) | 0.359 (2) | 0.037 (5)* | |
H1C42 | 0.569 (2) | 0.5062 (6) | 0.149 (2) | 0.034 (4)* | |
H1C52 | 0.349 (2) | 0.4570 (7) | 0.357 (3) | 0.064 (6)* | |
H3C52 | 0.346 (3) | 0.4548 (8) | 0.143 (3) | 0.077 (7)* | |
H2C52 | 0.485 (3) | 0.4287 (8) | 0.250 (3) | 0.070 (7)* | |
HO11 | 0.116 (2) | 0.3398 (7) | 0.271 (2) | 0.047 (6)* | |
HO41 | 0.245 (2) | 0.2527 (7) | 0.062 (3) | 0.066 (7)* | |
HO12 | 0.620 (2) | 0.3399 (7) | 0.239 (2) | 0.044 (6)* | |
HO22 | 0.838 (3) | 0.2587 (8) | 0.030 (3) | 0.089 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0205 (2) | 0.0251 (2) | 0.0209 (2) | −0.0009 (2) | 0.0003 (2) | 0.0016 (1) |
O11 | 0.0240 (6) | 0.0345 (6) | 0.0504 (7) | 0.0020 (5) | 0.0059 (5) | 0.0106 (5) |
O21 | 0.0417 (6) | 0.0374 (6) | 0.0219 (5) | −0.0049 (5) | −0.0032 (5) | 0.0011 (4) |
O31 | 0.0220 (5) | 0.0404 (6) | 0.0307 (6) | −0.0049 (5) | 0.0035 (4) | 0.0020 (5) |
O41 | 0.0392 (6) | 0.0308 (6) | 0.0243 (6) | −0.0089 (5) | 0.0031 (5) | −0.0015 (5) |
P2 | 0.0209 (2) | 0.0270 (2) | 0.0210 (2) | −0.0007 (2) | −0.001 (2) | −0.0002 (2) |
O12 | 0.0236 (6) | 0.0324 (6) | 0.0534 (8) | 0.0004 (5) | −0.0052 (5) | −0.0058 (5) |
O22 | 0.0548 (8) | 0.0333 (6) | 0.0218 (6) | −0.0036 (5) | 0.0049 (5) | 0.0013 (5) |
O32 | 0.0221 (5) | 0.0449 (7) | 0.0335 (6) | −0.0057 (5) | −0.0029 (4) | −0.0007 (5) |
O42 | 0.0358 (6) | 0.0314 (6) | 0.0238 (5) | −0.0054 (5) | −0.0018 (4) | 0.0026 (4) |
N1 | 0.0284 (7) | 0.0317 (8) | 0.0306 (8) | 0.0018 (6) | 0.0006 (7) | 0.0012 (6) |
C11 | 0.0280 (9) | 0.0314 (9) | 0.0318 (9) | −0.0007 (7) | −0.0038 (7) | −0.0012 (7) |
C21 | 0.0314 (9) | 0.0305 (9) | 0.043 (1) | 0.0001 (7) | −0.0000 (8) | −0.0005 (7) |
C31 | 0.035 (1) | 0.0317 (9) | 0.048 (1) | −0.0015 (7) | −0.0022 (9) | −0.0022 (8) |
C41 | 0.047 (1) | 0.0338 (9) | 0.043 (1) | 0.0045 (8) | −0.0009 (9) | −0.0014 (8) |
C51 | 0.070 (2) | 0.034 (1) | 0.060 (1) | −0.002 (1) | −0.000 (1) | 0.0005 (9) |
N2 | 0.0298 (7) | 0.0276 (7) | 0.0295 (8) | 0.0019 (6) | 0.0012 (7) | −0.0001 (6) |
C12 | 0.0265 (8) | 0.0336 (9) | 0.0330 (9) | −0.0015 (7) | 0.0021 (7) | 0.0020 (7) |
C22 | 0.0278 (9) | 0.0329 (9) | 0.044 (1) | 0.001 (7) | 0.0001 (8) | 0.0006 (8) |
C32 | 0.0338 (9) | 0.0318 (9) | 0.048 (1) | −0.0027 (7) | −0.0018 (9) | 0.0019 (8) |
C42 | 0.045 (1) | 0.0324 (9) | 0.044 (1) | 0.0023 (8) | 0.0012 (9) | 0.0011 (8) |
C52 | 0.073 (2) | 0.034 (1) | 0.060 (1) | −0.003 (1) | 0.003 (1) | −0.002 (1) |
Geometric parameters (Å, º) top
P1—O11 | 1.560 (1) | O31—N2v | 2.816 (2) |
P1—O21 | 1.504 (1) | O41—N2vi | 2.857 (2) |
P1—O31 | 1.498 (1) | P2—O12 | 1.556 (1) |
P1—O41 | 1.572 (1) | P2—O22 | 1.570 (1) |
O11—HO11 | 0.78 (2) | P2—O32 | 1.495 (1) |
O41—HO41 | 0.87 (2) | P2—O42 | 1.514 (1) |
N1—C11 | 1.488 (2) | O12—HO12 | 0.75 (2) |
C11—C21 | 1.514 (2) | O22—HO22 | 0.96 (2) |
C21—C31 | 1.519 (2) | N2—C12 | 1.484 (2) |
C31—C41 | 1.525 (3) | C12—C22 | 1.511 (2) |
C41—C51 | 1.526 (3) | C22—C32 | 1.520 (2) |
O11—O32i | 2.601 (2) | C32—C42 | 1.523 (3) |
O21—O22ii | 2.548 (2) | C42—C52 | 1.527 (3) |
O31—O12 | 2.591 (2) | O22—N1vii | 3.004 (2) |
O41—O42iii | 2.507 (1) | O32—N1viii | 2.797 (2) |
O21—N2iv | 2.859 (2) | O42—N1ix | 2.762 (2) |
| | | |
O11—P1—O21 | 110.51 (6) | O12—P2—O22 | 105.46 (6) |
O11—P1—O31 | 106.99 (6) | O12—P2—O32 | 107.31 (6) |
O11—P1—O41 | 107.05 (6) | O12—P2—O42 | 111.14 (6) |
O21—P1—O31 | 116.62 (6) | O22—P2—O32 | 111.26 (6) |
O21—P1—O41 | 105.33 (6) | O22—P2—O42 | 107.52 (6) |
O31—P1—O41 | 109.98 (6) | O32—P2—O42 | 113.87 (6) |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) −x+1/2, y−1/2, −z+1/2; (vii) −x+2, −y+1, −z; (viii) −x+2, −y+1, −z+1; (ix) −x+3/2, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | D···A | D—H···A |
O11—HO11···O32i | 0.78 (2) | 2.600 (1) | 174 (2) |
O41—HO41···O42iii | 0.87 (2) | 2.507 (1) | 177 (2) |
O22—HO22···O21x | 0.96 (2) | 2.547 (2) | 171 (2) |
O12—HO12···O31 | 0.75 (2) | 2.591 (1) | 172 (2) |
N1—H1N1···O32viii | 0.88 (2) | 2.797 (2) | 170 (2) |
N1—H2N1···O42xi | 0.91 (2) | 2.761 (2) | 166 (2) |
N1—H3N1···O22vii | 0.82 (2) | 3.003 (2) | 156 (2) |
N2—H1N2···O21iv | 0.85 (2) | 2.859 (2) | 162 (2) |
N2—H2N2···O41xii | 0.87 (2) | 2.857 (2) | 162 (2) |
N2—H3N2···O31v | 0.91 (2) | 2.815 (2) | 161 (2) |
Symmetry codes: (i) x−1, y, z; (iii) x−1/2, −y+1/2, z−1/2; (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, z−1/2; (xi) −x+3/2, y+1/2, −z+1/2; (xii) −x+1/2, y+1/2, −z+1/2. |
Crystal data top
C6H16N+·H2O4P− | F(000) = 864 |
Mr = 199.19 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 50 reflections |
a = 9.143 (1) Å | θ = 5.6–22.8° |
b = 29.637 (8) Å | µ = 0.26 mm−1 |
c = 7.299 (1) Å | T = 290 K |
β = 90.86 (1)° | Plate, colourless |
V = 1977.7 (7) Å3 | 0.33 × 0.20 × 0.10 mm |
Z = 8 | |
Data collection top
Hilger & Watts diffractometer | θmax = 25° |
ω–2θ scans | h = −10→10 |
5446 measured reflections | k = −35→35 |
3452 independent reflections | l = 0→8 |
2167 reflections with I > 3σ(I) | 3 standard reflections every 30 reflections |
Rint = 0.060 | intensity decay: 6.0% |
Refinement top
Refinement on F | 0 constraints |
Least-squares matrix: full with fixed elements per cycle | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.050 | w = (σ2(Fo) + 0.0001(Fo)2)-1 |
wR(F2) = 0.056 | (Δ/σ)max = 0.01 |
S = 1.71 | Δρmax = 0.46 e Å−3 |
3452 reflections | Δρmin = −0.54 e Å−3 |
363 parameters | Extinction correction: Becker & Coppens, 1974, type II |
4 restraints | Extinction coefficient: 0.00017 (2) |
Crystal data top
C6H16N+·H2O4P− | V = 1977.7 (7) Å3 |
Mr = 199.19 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.143 (1) Å | µ = 0.26 mm−1 |
b = 29.637 (8) Å | T = 290 K |
c = 7.299 (1) Å | 0.33 × 0.20 × 0.10 mm |
β = 90.86 (1)° | |
Data collection top
Hilger & Watts diffractometer | Rint = 0.060 |
5446 measured reflections | 3 standard reflections every 30 reflections |
3452 independent reflections | intensity decay: 6.0% |
2167 reflections with I > 3σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 4 restraints |
wR(F2) = 0.056 | All H-atom parameters refined |
S = 1.71 | Δρmax = 0.46 e Å−3 |
3452 reflections | Δρmin = −0.54 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
P1 | 0.08787 (7) | 0.30071 (2) | 0.25532 (9) | 0.0232 (2) | |
O11 | −0.0327 (2) | 0.33731 (6) | 0.2298 (3) | 0.0368 (7) | |
O21 | 0.1194 (2) | 0.29233 (6) | 0.4548 (2) | 0.0335 (6) | |
O31 | 0.2159 (2) | 0.31489 (6) | 0.1415 (2) | 0.0324 (6) | |
O41 | 0.0230 (2) | 0.25539 (6) | 0.1804 (3) | 0.0334 (6) | |
P2 | 0.58373 (7) | 0.29784 (2) | 0.26410 (9) | 0.0236 (2) | |
O12 | 0.4712 (2) | 0.33714 (6) | 0.2666 (3) | 0.0371 (7) | |
O22 | 0.6176 (2) | 0.28995 (7) | 0.0574 (2) | 0.0379 (7) | |
O32 | 0.7172 (2) | 0.31308 (7) | 0.3665 (2) | 0.0344 (6) | |
O42 | 0.5179 (2) | 0.25485 (6) | 0.3389 (2) | 0.0302 (6) | |
N1 | 0.1904 (3) | 0.69309 (9) | 0.2676 (4) | 0.0307 (8) | |
C11 | 0.1059 (3) | 0.65055 (9) | 0.2485 (4) | 0.0315 (9) | |
C21 | 0.2023 (3) | 0.60953 (9) | 0.2565 (5) | 0.035 (1) | |
C31 | 0.1128 (3) | 0.5666 (1) | 0.2502 (5) | 0.038 (1) | |
C41 | 0.2032 (4) | 0.5236 (1) | 0.2529 (5) | 0.038 (1) | |
C51 | 0.1132 (4) | 0.4807 (1) | 0.2502 (6) | 0.048 (1) | |
C61 | 0.2029 (6) | 0.4381 (1) | 0.2539 (6) | 0.058 (2) | |
N2 | 0.6999 (3) | 0.69255 (8) | 0.2263 (4) | 0.0306 (8) | |
C12 | 0.6110 (3) | 0.65082 (9) | 0.2444 (4) | 0.0316 (9) | |
C22 | 0.7048 (3) | 0.60921 (9) | 0.2425 (4) | 0.0334 (9) | |
C32 | 0.6133 (3) | 0.56635 (9) | 0.2489 (5) | 0.039 (1) | |
C42 | 0.7031 (4) | 0.5236 (1) | 0.2468 (5) | 0.039 (1) | |
C52 | 0.6126 (4) | 0.4806 (1) | 0.2489 (6) | 0.048 (1) | |
C62 | 0.7008 (6) | 0.4380 (1) | 0.2467 (6) | 0.060 (2) | |
H1N2 | 0.760 (3) | 0.691 (1) | 0.302 (4) | 0.036 (9)* | |
H2N2 | 0.642 (3) | 0.7182 (9) | 0.241 (3) | 0.022 (7)* | |
H3N2 | 0.741 (3) | 0.6918 (9) | 0.107 (4) | 0.042 (9)* | |
H1C12 | 0.564 (3) | 0.6557 (9) | 0.349 (4) | 0.034 (8)* | |
H2C12 | 0.540 (3) | 0.6499 (8) | 0.143 (4) | 0.029 (7)* | |
H1C22 | 0.777 (4) | 0.608 (1) | 0.114 (5) | 0.06 (1)* | |
H2C22 | 0.775 (3) | 0.6078 (8) | 0.344 (4) | 0.033 (7)* | |
H1C32 | 0.548 (4) | 0.567 (1) | 0.365 (5) | 0.06 (1)* | |
H2C32 | 0.553 (3) | 0.5672 (9) | 0.150 (4) | 0.041 (9)* | |
H1C42 | 0.755 (3) | 0.5232 (9) | 0.137 (5) | 0.040 (9)* | |
H2C42 | 0.769 (4) | 0.523 (1) | 0.350 (5) | 0.06 (1)* | |
H1C52 | 0.540 (4) | 0.482 (1) | 0.150 (5) | 0.06 (1)* | |
H2C52 | 0.549 (4) | 0.481 (1) | 0.360 (6) | 0.08 (1)* | |
H1C62 | 0.775 (5) | 0.437 (1) | 0.342 (6) | 0.09 (1)* | |
H2C62 | 0.639 (4) | 0.413 (1) | 0.242 (5) | 0.08 (1)* | |
H3C62 | 0.760 (4) | 0.437 (1) | 0.133 (6) | 0.08 (1)* | |
H1N1 | 0.233 (3) | 0.6935 (9) | 0.383 (4) | 0.036 (8)* | |
H2N1 | 0.128 (4) | 0.716 (1) | 0.255 (4) | 0.048 (9)* | |
H3N1 | 0.257 (4) | 0.692 (1) | 0.200 (4) | 0.04 (1)* | |
H2C11 | 0.050 (4) | 0.653 (1) | 0.137 (5) | 0.057 (9)* | |
H1C11 | 0.031 (4) | 0.651 (1) | 0.337 (5) | 0.05 (1)* | |
H1C21 | 0.269 (3) | 0.610 (1) | 0.162 (4) | 0.047 (9)* | |
H2C21 | 0.266 (4) | 0.610 (1) | 0.379 (5) | 0.06 (1)* | |
H1C31 | 0.052 (3) | 0.5656 (9) | 0.344 (4) | 0.035 (9)* | |
H2C31 | 0.058 (3) | 0.5663 (9) | 0.144 (4) | 0.035 (8)* | |
H1C41 | 0.270 (4) | 0.521 (1) | 0.157 (6) | 0.07 (1)* | |
H2C41 | 0.270 (3) | 0.5229 (9) | 0.371 (5) | 0.048 (9)* | |
H1C51 | 0.047 (4) | 0.483 (1) | 0.139 (5) | 0.07 (1)* | |
H2C51 | 0.059 (3) | 0.4819 (9) | 0.359 (4) | 0.030 (8)* | |
H1C61 | 0.262 (4) | 0.434 (1) | 0.364 (6) | 0.07 (1)* | |
H2C61 | 0.140 (5) | 0.416 (2) | 0.246 (6) | 0.09 (1)* | |
H3C61 | 0.259 (6) | 0.437 (2) | 0.154 (7) | 0.11 (2)* | |
HO11 | −0.117 (2) | 0.329 (1) | 0.257 (4) | 0.05 (1)* | |
HO41 | 0.017 (3) | 0.253 (1) | 0.065 (1) | 0.06 (1)* | |
HO12 | 0.391 (2) | 0.327 (1) | 0.224 (4) | 0.05 (1)* | |
HO22 | 0.606 (3) | 0.2624 (4) | 0.027 (4) | 0.041 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0220 (3) | 0.0267 (4) | 0.0209 (3) | −0.0013 (3) | 0.0023 (3) | 0.0017 (3) |
O11 | 0.026 (1) | 0.034 (1) | 0.051 (1) | 0.0021 (9) | 0.0056 (9) | 0.0087 (9) |
O21 | 0.045 (1) | 0.036 (1) | 0.020 (1) | −0.0047 (9) | −0.0017 (8) | 0.0009 (8) |
O31 | 0.0228 (9) | 0.045 (1) | 0.029 (1) | −0.0075 (8) | 0.0054 (7) | 0.0020 (8) |
O41 | 0.043 (1) | 0.034 (1) | 0.022 (1) | −0.0113 (9) | 0.0039 (9) | −0.0011 (9) |
P2 | 0.0216 (3) | 0.0269 (4) | 0.0222 (3) | −0.0007 (3) | −0.0002 (3) | 0.0001 (3) |
O12 | 0.023 (1) | 0.034 (1) | 0.054 (1) | 0.0022 (8) | −0.0009 (9) | −0.0070 (9) |
O22 | 0.056 (1) | 0.036 (1) | 0.021 (1) | −0.009 (1) | 0.0063 (9) | −0.0007 (9) |
O32 | 0.0227 (9) | 0.048 (1) | 0.032 (1) | −0.0034 (8) | −0.0015 (8) | 0.0003 (9) |
O42 | 0.036 (1) | 0.034 (1) | 0.021 (1) | −0.0080 (8) | 0.0019 (8) | 0.0031 (8) |
N1 | 0.029 (1) | 0.030 (1) | 0.033 (2) | 0.003 (1) | 0.003 (1) | 0.003 (1) |
C11 | 0.027 (2) | 0.030 (1) | 0.037 (2) | −0.001 (1) | −0.002 (1) | −0.005 (1) |
C21 | 0.033 (2) | 0.029 (2) | 0.044 (2) | 0.001 (1) | 0.004 (2) | 0.001 (1) |
C31 | 0.039 (2) | 0.033 (2) | 0.042 (2) | −0.004 (1) | 0.000 (2) | −0.001 (1) |
C41 | 0.043 (2) | 0.031 (2) | 0.041 (2) | 0.000 (1) | −0.001 (2) | −0.004 (1) |
C51 | 0.062 (2) | 0.037 (2) | 0.044 (2) | −0.007 (2) | 0.006 (2) | −0.002 (2) |
C61 | 0.094 (3) | 0.031 (2) | 0.051 (3) | −0.001 (2) | −0.003 (3) | −0.003 (2) |
N2 | 0.031 (1) | 0.031 (1) | 0.030 (1) | 0.005 (1) | −0.001 (1) | −0.002 (1) |
C12 | 0.028 (2) | 0.034 (2) | 0.033 (2) | −0.004 (1) | 0.006 (1) | 0.003 (1) |
C22 | 0.031 (2) | 0.028 (2) | 0.040 (2) | 0.000 (1) | 0.001 (1) | −0.001 (1) |
C32 | 0.040 (2) | 0.030 (2) | 0.047 (2) | −0.002 (1) | −0.001 (2) | 0.002 (1) |
C42 | 0.050 (2) | 0.031 (2) | 0.036 (2) | 0.001 (1) | 0.005 (2) | 0.001 (1) |
C52 | 0.060 (2) | 0.032 (2) | 0.052 (2) | −0.010 (2) | −0.002 (2) | −0.002 (2) |
C62 | 0.094 (3) | 0.031 (2) | 0.054 (3) | −0.008 (2) | 0.007 (3) | 0.001 (2) |
Geometric parameters (Å, º) top
P1—O11 | 1.556 (3) | C51—C61 | 1.505 (6) |
P1—O21 | 1.501 (3) | N12—C12 | 1.486 (4) |
P1—O31 | 1.505 (3) | C12—C22 | 1.501 (4) |
P1—O41 | 1.563 (3) | C22—C32 | 1.523 (4) |
O11—HO11 | 0.84 (2) | C32—C42 | 1.509 (5) |
O41—HO41 | 0.85 (1) | C42—C52 | 1.521 (5) |
P2—O12 | 1.554 (2) | C52—C62 | 1.495 (6) |
P2—O22 | 1.563 (2) | O11—O32i | 2.610 (3) |
P2—O32 | 1.492 (2) | O21—O22ii | 2.550 (3) |
P2—O42 | 1.515 (2) | O31—O12 | 2.579 (3) |
O12—HO12 | 0.85 (2) | O41—O42iii | 2.511 (3) |
O22—HO22 | 0.85 (1) | O21—N2iv | 2.870 (3) |
N11—C11 | 1.484 (4) | O31—N2v | 2.813 (3) |
C11—C21 | 1.501 (4) | O41—N2vi | 2.850 (3) |
C21—C31 | 1.514 (5) | O22—N1v | 3.014 (3) |
C31—C41 | 1.519 (5) | O32—N1iv | 2.796 (3) |
C41—C51 | 1.515 (5) | O42—N1vi | 2.746 (3) |
| | | |
O11—P1—O21 | 110.91 (11) | O12—P2—O22 | 105.34 (11) |
O11—P1—O31 | 107.13 (11) | O12—P2—O32 | 107.69 (11) |
O11—P1—O41 | 107.01 (10) | O12—P2—O42 | 111.07 (10) |
O21—P1—O31 | 116.25 (10) | O22—P2—O32 | 110.89 (11) |
O21—P1—O41 | 105.27 (10) | O22—P2—O42 | 107.93 (10) |
O31—P1—O41 | 109.93 (10) | O32—P2—O42 | 113.62 (10) |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) −x+1/2, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | D···A | D—H···A |
O11—HO11···O32i | 0.84 (2) | 2.610 (3) | 167 (3) |
O41—HO41···O42iii | 0.85 (1) | 2.511 (3) | 174 (3) |
O22—HO22···O21vii | 0.85 (1) | 2.551 (3) | 168 (3) |
O12—HO12···O31 | 0.85 (2) | 2.580 (3) | 172 (3) |
N1—H1N1···O32iv | 0.92 (3) | 2.796 (3) | 167 (3) |
N1—H2N1···O42viii | 0.88 (3) | 2.746 (3) | 163 (3) |
N1—H3N1···O22v | 0.79 (3) | 3.014 (3) | 155 (3) |
N2—H1N2···O21iv | 0.78 (3) | 2.870 (3) | 159 (3) |
N2—H2N2···O41viii | 0.93 (3) | 2.850 (3) | 158 (2) |
N2—H3N2···O31v | 0.95 (4) | 2.813 (3) | 168 (3) |
Symmetry codes: (i) x−1, y, z; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vii) x+1/2, −y+1/2, z−1/2; (viii) −x+1/2, y+1/2, −z+1/2. |
Crystal data top
C9H22N+·H2O4P− | F(000) = 1056 |
Mr = 241.27 | Dx = 1.284 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 50 reflections |
a = 9.138 (3) Å | θ = 4.3–18.0° |
b = 36.984 (9) Å | µ = 0.22 mm−1 |
c = 7.383 (2) Å | T = 290 K |
β = 90.88 (2)° | Plate, colourless |
V = 2495 (1) Å3 | 0.33 × 0.21 × 0.10 mm |
Z = 8 | |
Data collection top
Hilger & Watts diffractometer | Rint = 0.073 |
ω–2θ scans | θmax = 26° |
Absorption correction: gaussian AGNOST C, Templeton & Templeton (1978) | h = 0→11 |
Tmin = 0.942, Tmax = 0.978 | k = −45→45 |
13662 measured reflections | l = −9→9 |
4906 independent reflections | 3 standard reflections every 30 reflections |
2948 reflections with I > 3σ(I) | intensity decay: 7.0% |
Refinement top
Refinement on F | 3 constraints |
Least-squares matrix: full with fixed elements per cycle | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.053 | w = (σ2(Fo) + 0.0001(Fo)2)-1 |
wR(F2) = 0.058 | (Δ/σ)max = 0.01 |
S = 1.91 | Δρmax = 0.66 e Å−3 |
4906 reflections | Δρmin = −0.59 e Å−3 |
466 parameters | Extinction correction: Becker & Coppens, 1974, type II |
2 restraints | Extinction coefficient: 0.00028 (3) |
Crystal data top
C9H22N+·H2O4P− | V = 2495 (1) Å3 |
Mr = 241.27 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.138 (3) Å | µ = 0.22 mm−1 |
b = 36.984 (9) Å | T = 290 K |
c = 7.383 (2) Å | 0.33 × 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 = 0.978 | 3 standard reflections every 30 reflections |
13662 measured reflections | intensity decay: 7.0% |
4906 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 2 restraints |
wR(F2) = 0.058 | All H-atom parameters refined |
S = 1.91 | Δρmax = 0.66 e Å−3 |
4906 reflections | Δρmin = −0.59 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.06381 (7) | 0.29018 (2) | 0.25460 (7) | 0.0223 (2) | Uani |
O11 | −0.0570 (2) | 0.31936 (5) | 0.2272 (3) | 0.0353 (6) | Uani |
O21 | 0.0935 (2) | 0.28355 (4) | 0.4522 (2) | 0.0334 (5) | Uani |
O31 | 0.1915 (2) | 0.30118 (4) | 0.1433 (2) | 0.0295 (5) | Uani |
O41 | −0.0019 (2) | 0.25370 (4) | 0.1801 (2) | 0.0299 (5) | Uani |
P2 | 0.55976 (7) | 0.28770 (2) | 0.26507 (7) | 0.0222 (2) | Uani |
O12 | 0.4483 (2) | 0.31938 (4) | 0.2715 (2) | 0.0347 (6) | Uani |
O22 | 0.5914 (2) | 0.28178 (5) | 0.0598 (2) | 0.0384 (6) | Uani |
O32 | 0.6946 (2) | 0.29976 (4) | 0.3648 (2) | 0.0318 (5) | Uani |
O42 | 0.4944 (2) | 0.25338 (4) | 0.3385 (2) | 0.0304 (5) | Uani |
N1 | 0.2188 (3) | 0.70564 (6) | 0.2699 (3) | 0.0307 (7) | Uani |
C11 | 0.1385 (3) | 0.67063 (6) | 0.2483 (3) | 0.0293 (8) | Uani |
C21 | 0.2380 (3) | 0.63869 (6) | 0.2569 (4) | 0.0327 (8) | Uani |
C31 | 0.1528 (3) | 0.60349 (7) | 0.2494 (4) | 0.0354 (9) | Uani |
C41 | 0.2475 (3) | 0.56978 (6) | 0.2528 (4) | 0.0323 (8) | Uani |
C51 | 0.1588 (3) | 0.53509 (6) | 0.2505 (4) | 0.0341 (9) | Uani |
C61 | 0.2521 (3) | 0.50091 (6) | 0.2521 (3) | 0.0328 (8) | Uani |
C71 | 0.1638 (3) | 0.46631 (6) | 0.2525 (4) | 0.0346 (9) | Uani |
C81 | 0.2563 (4) | 0.43249 (7) | 0.2546 (4) | 0.0388 (9) | Uani |
C91 | 0.1660 (5) | 0.39808 (8) | 0.2564 (5) | 0.053 (1) | Uani |
N2 | 0.7297 (3) | 0.70470 (6) | 0.2256 (3) | 0.0291 (7) | Uani |
C12 | 0.6438 (3) | 0.67100 (6) | 0.2436 (4) | 0.0302 (8) | Uani |
C22 | 0.7400 (3) | 0.63820 (6) | 0.2408 (4) | 0.0311 (8) | Uani |
C32 | 0.6536 (3) | 0.60324 (7) | 0.2478 (4) | 0.0349 (9) | Uani |
C42 | 0.7471 (3) | 0.56961 (6) | 0.2471 (4) | 0.0326 (8) | Uani |
C52 | 0.6589 (3) | 0.53493 (7) | 0.2467 (4) | 0.0347 (9) | Uani |
C62 | 0.7518 (3) | 0.50082 (6) | 0.2487 (4) | 0.0328 (8) | Uani |
C72 | 0.6638 (3) | 0.46617 (7) | 0.2461 (4) | 0.0353 (9) | Uani |
C82 | 0.7556 (4) | 0.43219 (7) | 0.2476 (4) | 0.0396 (9) | Uani |
C92 | 0.6655 (4) | 0.39767 (8) | 0.2429 (5) | 0.052 (1) | Uani |
H1N2 | 0.807 (2) | 0.7064 (9) | 0.300 (3) | 0.08 (1) | Uiso |
H2N2 | 0.675 (3) | 0.7212 (7) | 0.233 (3) | 0.031 (7) | Uiso |
H3N2 | 0.770 (3) | 0.7041 (7) | 0.109 (4) | 0.053 (8) | Uiso |
H2C12 | 0.576 (3) | 0.6700 (6) | 0.149 (3) | 0.025 (6) | Uiso |
H1C12 | 0.591 (3) | 0.6746 (7) | 0.354 (3) | 0.045 (7) | Uiso |
H1C22 | 0.797 (3) | 0.6393 (8) | 0.139 (4) | 0.059 (9) | Uiso |
H2C22 | 0.811 (3) | 0.6397 (7) | 0.350 (3) | 0.041 (7) | Uiso |
H1C32 | 0.594 (3) | 0.6045 (7) | 0.353 (3) | 0.046 (8) | Uiso |
H2C32 | 0.592 (2) | 0.6022 (6) | 0.151 (3) | 0.032 (7) | Uiso |
H1C42 | 0.813 (3) | 0.5707 (7) | 0.135 (3) | 0.044 (7) | Uiso |
H2C42 | 0.815 (3) | 0.5705 (7) | 0.349 (4) | 0.047 (8) | Uiso |
H1C52 | 0.597 (3) | 0.5353 (7) | 0.140 (4) | 0.042 (8) | Uiso |
H2C52 | 0.597 (3) | 0.5343 (7) | 0.353 (4) | 0.046 (8) | Uiso |
H1C62 | 0.814 (3) | 0.5028 (6) | 0.148 (3) | 0.028 (6) | Uiso |
H2C62 | 0.825 (3) | 0.5019 (7) | 0.358 (4) | 0.046 (8) | Uiso |
H1C72 | 0.598 (3) | 0.4663 (7) | 0.139 (3) | 0.037 (7) | Uiso |
H2C72 | 0.600 (3) | 0.4661 (6) | 0.352 (3) | 0.030 (6) | Uiso |
H1C82 | 0.814 (3) | 0.4328 (7) | 0.142 (4) | 0.045 (8) | Uiso |
H2C82 | 0.822 (3) | 0.4329 (7) | 0.358 (4) | 0.040 (7) | Uiso |
H1C92 | 0.603 (3) | 0.3956 (7) | 0.349 (4) | 0.052 (8) | Uiso |
H2C92 | 0.730 (4) | 0.377 (1) | 0.238 (4) | 0.08 (1) | Uiso |
H3C92 | 0.607 (4) | 0.3951 (8) | 0.134 (4) | 0.06 (1) | Uiso |
H1N1 | 0.253 (3) | 0.7068 (8) | 0.373 (4) | 0.053 (9) | Uiso |
H2N1 | 0.153 (4) | 0.7257 (9) | 0.245 (4) | 0.07 (1) | Uiso |
H3N1 | 0.285 (4) | 0.7064 (9) | 0.190 (4) | 0.07 (1) | Uiso |
H1C11 | 0.072 (3) | 0.6696 (7) | 0.341 (3) | 0.047 (8) | Uiso |
H2C11 | 0.096 (3) | 0.6728 (6) | 0.122 (3) | 0.035 (7) | Uiso |
H2C21 | 0.288 (3) | 0.6402 (8) | 0.358 (4) | 0.06 (1) | Uiso |
H1C21 | 0.306 (3) | 0.6382 (7) | 0.156 (3) | 0.047 (8) | Uiso |
H1C31 | 0.082 (3) | 0.6033 (7) | 0.343 (4) | 0.051 (8) | Uiso |
H2C31 | 0.078 (4) | 0.6026 (8) | 0.144 (4) | 0.07 (1) | Uiso |
H2C41 | 0.307 (3) | 0.5701 (6) | 0.355 (3) | 0.022 (6) | Uiso |
H1C41 | 0.308 (3) | 0.5702 (6) | 0.152 (3) | 0.031 (7) | Uiso |
H1C51 | 0.094 (3) | 0.5350 (7) | 0.143 (4) | 0.049 (8) | Uiso |
H2C51 | 0.092 (3) | 0.5340 (7) | 0.360 (4) | 0.051 (8) | Uiso |
H1C61 | 0.320 (3) | 0.5006 (6) | 0.141 (3) | 0.035 (6) | Uiso |
H2C61 | 0.317 (3) | 0.5029 (6) | 0.347 (3) | 0.028 (6) | Uiso |
H1C71 | 0.099 (3) | 0.4649 (7) | 0.143 (4) | 0.051 (8) | Uiso |
H2C71 | 0.095 (3) | 0.4650 (7) | 0.367 (4) | 0.048 (8) | Uiso |
H1C81 | 0.320 (3) | 0.4309 (6) | 0.145 (3) | 0.035 (7) | Uiso |
H2C81 | 0.326 (3) | 0.4338 (6) | 0.357 (3) | 0.031 (7) | Uiso |
H1C91 | 0.098 (4) | 0.3962 (9) | 0.370 (5) | 0.09 (1) | Uiso |
H2C91 | 0.229 (4) | 0.378 (1) | 0.254 (5) | 0.09 (1) | Uiso |
H3C91 | 0.097 (4) | 0.3963 (8) | 0.154 (4) | 0.06 (1) | Uiso |
HO11 | −0.123 (5) | 0.317 (1) | 0.286 (5) | 0.10 (2) | Uiso |
HO41 | −0.003 (4) | 0.2519 (9) | 0.066 (4) | 0.08 (1) | Uiso |
HO12 | 0.371 (2) | 0.3133 (6) | 0.247 (3) | 0.011 (6) | Uiso |
HO22 | 0.581 (3) | 0.2610 (8) | 0.034 (3) | 0.045 (8) | Uiso |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0211 (3) | 0.0239 (3) | 0.0220 (3) | −0.0016 (3) | −0.0001 (2) | 0.0017 (2) |
O11 | 0.027 (1) | 0.0293 (9) | 0.050 (1) | 0.0034 (8) | 0.0027 (8) | 0.0097 (7) |
O21 | 0.047 (1) | 0.0315 (9) | 0.0216 (7) | −0.0024 (8) | −0.0009 (7) | −0.0002 (6) |
O31 | 0.0256 (9) | 0.035 (1) | 0.0282 (8) | −0.0043 (7) | 0.0037 (6) | 0.0024 (6) |
O41 | 0.041 (1) | 0.0256 (8) | 0.0236 (8) | −0.0081 (7) | 0.0010 (7) | −0.0013 (6) |
P2 | 0.0215 (3) | 0.0230 (3) | 0.0221 (3) | −0.0007 (3) | −0.0013 (2) | 0.0005 (2) |
O12 | 0.022 (1) | 0.027 (1) | 0.055 (1) | 0.0002 (8) | −0.0040 (8) | −0.0067 (7) |
O22 | 0.062 (1) | 0.029 (1) | 0.0245 (8) | −0.0097 (9) | 0.0063 (7) | 0.0005 (7) |
O32 | 0.0241 (8) | 0.041 (1) | 0.0304 (8) | −0.0046 (7) | −0.0034 (6) | −0.0020 (6) |
O42 | 0.0403 (9) | 0.0273 (8) | 0.0236 (8) | −0.0056 (7) | −0.0005 (6) | 0.0014 (6) |
N1 | 0.031 (1) | 0.024 (1) | 0.037 (1) | −0.0016 (9) | 0.001 (1) | 0.0020 (9) |
C11 | 0.027 (1) | 0.025 (1) | 0.035 (1) | −0.004 (1) | −0.002 (1) | 0.000 (1) |
C21 | 0.030 (1) | 0.024 (1) | 0.044 (2) | −0.001 (1) | 0.002 (1) | −0.002 (1) |
C31 | 0.034 (2) | 0.024 (1) | 0.048 (2) | 0.004 (1) | 0.000 (1) | 0.001 (1) |
C41 | 0.032 (1) | 0.029 (1) | 0.036 (1) | 0.003 (1) | −0.001 (1) | −0.001 (1) |
C51 | 0.040 (2) | 0.022 (1) | 0.040 (2) | −0.002 (1) | −0.002 (1) | 0.000 (1) |
C61 | 0.035 (1) | 0.028 (1) | 0.035 (1) | −0.004 (1) | −0.003 (1) | −0.003 (1) |
C71 | 0.040 (2) | 0.023 (1) | 0.041 (2) | 0.000 (1) | 0.000 (1) | −0.001 (1) |
C81 | 0.045 (2) | 0.033 (1) | 0.038 (1) | 0.004 (1) | −0.001 (1) | −0.001 (1) |
C91 | 0.075 (3) | 0.027 (2) | 0.058 (2) | −0.005 (2) | −0.002 (2) | −0.003 (1) |
N2 | 0.031 (1) | 0.023 (1) | 0.034 (1) | 0.003 (1) | 0.000 (1) | −0.0020 (8) |
C12 | 0.027 (1) | 0.027 (1) | 0.037 (1) | −0.001 (1) | 0.003 (1) | 0.001 (1) |
C22 | 0.029 (1) | 0.025 (1) | 0.040 (1) | 0.000 (1) | −0.003 (1) | −0.001 (1) |
C32 | 0.032 (2) | 0.029 (1) | 0.044 (2) | −0.003 (1) | −0.002 (1) | 0.001 (1) |
C42 | 0.035 (1) | 0.026 (1) | 0.037 (1) | −0.003 (1) | −0.003 (1) | 0.000 (1) |
C52 | 0.036 (2) | 0.027 (1) | 0.041 (2) | −0.003 (1) | 0.002 (1) | −0.003 (1) |
C62 | 0.036 (1) | 0.025 (1) | 0.037 (1) | −0.002 (1) | 0.001 (1) | 0.001 (1) |
C72 | 0.042 (2) | 0.027 (1) | 0.037 (1) | −0.004 (1) | −0.001 (1) | 0.002 (1) |
C82 | 0.051 (2) | 0.030 (1) | 0.037 (1) | −0.001 (1) | 0.000 (1) | 0.000 (1) |
C92 | 0.071 (2) | 0.027 (2) | 0.056 (2) | −0.001 (2) | −0.004 (2) | 0.003 (1) |
Geometric parameters (Å, º) top
P1—O11 | 1.555 (2) | C71—H2C71 | 1.06 (3) |
P1—O21 | 1.500 (1) | C81—H1C81 | 1.00 (2) |
P1—O31 | 1.493 (2) | C81—H2C81 | 0.98 (3) |
P1—O41 | 1.573 (2) | C91—H1C91 | 1.05 (4) |
O11—HO11 | 0.75 (4) | C91—H2C91 | 0.95 (4) |
O41—HO41 | 0.85 (3) | C91—H3C91 | 0.98 (3) |
P2—O12 | 1.553 (2) | N2—C12 | 1.480 (3) |
P2—O22 | 1.562 (2) | C12—C22 | 1.499 (3) |
P2—O32 | 1.494 (2) | C22—C32 | 1.517 (4) |
P2—O42 | 1.508 (2) | C32—C42 | 1.509 (4) |
O12—HO12 | 0.76 (2) | C42—C52 | 1.515 (4) |
O22—HO22 | 0.80 (3) | C52—C62 | 1.521 (4) |
N1—C11 | 1.496 (3) | C62—C72 | 1.513 (4) |
C11—C21 | 1.492 (3) | C72—C82 | 1.511 (4) |
C21—C31 | 1.518 (4) | C82—C92 | 1.519 (4) |
C31—C41 | 1.518 (4) | N2—H1N2 | 0.89 (2) |
C41—C51 | 1.518 (4) | N2—H2N2 | 0.79 (3) |
C51—C61 | 1.525 (4) | N2—H3N2 | 0.94 (3) |
C61—C71 | 1.513 (4) | C12—H2C12 | 0.93 (2) |
C71—C81 | 1.510 (4) | C12—H1C12 | 0.97 (3) |
C81—C91 | 1.517 (4) | C22—H1C22 | 0.92 (3) |
N1—H1N1 | 0.82 (3) | C22—H2C22 | 1.03 (3) |
N1—H2N1 | 0.97 (3) | C32—H1C32 | 0.96 (2) |
N1—H3N1 | 0.85 (3) | C32—H2C32 | 0.91 (2) |
C11—H1C11 | 0.93 (3) | C42—H1C42 | 1.03 (3) |
C11—H2C11 | 1.00 (2) | C42—H2C42 | 0.97 (3) |
C21—H2C21 | 0.87 (3) | C52—H1C52 | 0.96 (3) |
C21—H1C21 | 0.98 (3) | C52—H2C52 | 0.97 (3) |
C31—H1C31 | 0.95 (3) | C62—H1C62 | 0.94 (2) |
C31—H2C31 | 1.03 (3) | C62—H2C62 | 1.04 (3) |
C41—H2C41 | 0.92 (2) | C72—H1C72 | 0.98 (3) |
C41—H1C41 | 0.93 (2) | C72—H2C72 | 0.98 (2) |
C51—H1C51 | 0.99 (3) | C82—H1C82 | 0.95 (3) |
C51—H2C51 | 1.02 (3) | C82—H2C82 | 1.01 (3) |
C61—H1C61 | 1.04 (2) | C92—H1C92 | 0.98 (3) |
C61—H2C61 | 0.92 (2) | C92—H2C92 | 0.97 (4) |
C71—H1C71 | 1.00 (3) | C92—H3C92 | 0.96 (3) |
| | | |
O11—P1—O21 | 110.95 (10) | O12—P2—O22 | 105.45 (10) |
O11—P1—O31 | 107.37 (9) | O12—P2—O32 | 107.22 (10) |
O11—P1—O41 | 106.45 (9) | O12—P2—O42 | 111.13 (10) |
O21—P1—O31 | 116.63 (9) | O22—P2—O32 | 110.89 (10) |
O21—P1—O41 | 105.22 (9) | O22—P2—O42 | 108.11 (9) |
O31—P1—O41 | 109.78 (9) | O32—P2—O42 | 113.74 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | D···A | D—H···A |
O11—HO11···O32i | 0.75 (4) | 2.604 (2) | 160 (4) |
O41—HO41···O42ii | 0.85 (3) | 2.535 (2) | 178 (4) |
O22—HO22···O21iii | 0.80 (3) | 2.544 (2) | 167 (3) |
O12—HO12···O31 | 0.76 (2) | 2.606 (2) | 169 (2) |
N1iv—H1N1···O32v | 0.82 (3) | 2.806 (3) | 167 (3) |
N1vi—H2N1···O42vii | 0.97 (3) | 2.739 (3) | 164 (3) |
N1—H3N1···O22 | 0.85 (3) | 3.047 (3) | 162 (3) |
N2—H1N2···O21v | 0.89 (2) | 2.888 (3) | 153 (2) |
N2—H2N2···O41vii | 0.79 (3) | 2.854 (3) | 161 (2) |
N2—H3N2···O31viii | 0.94 (3) | 2.837 (3) | 167 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) x+1, y+1, z+1; (v) −x+1, −y+1, −z+1; (vi) x, y−1, 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 formula | C5H14N+·H2O4P− | C6H16N+·H2O4P− | C9H22N+·H2O4P− |
Mr | 185.16 | 199.19 | 241.27 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 290 | 290 | 290 |
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) |
V (Å3) | 1806.2 (5) | 1977.7 (7) | 2495 (1) |
Z | 8 | 8 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.28 | 0.26 | 0.22 |
Crystal size (mm) | 0.56 × 0.32 × 0.15 | 0.33 × 0.20 × 0.10 | 0.33 × 0.21 × 0.10 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4-MACHIII-PC diffractometer | Hilger & Watts diffractometer | Hilger & Watts diffractometer |
Absorption correction | – | – | Gaussian AGNOST C, Templeton & Templeton (1978) |
Tmin, Tmax | – | – | 0.942, 0.978 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 3418, 3167, 2417 | 5446, 3452, 2167 | 13662, 4906, 2948 |
Rint | 0.034 | 0.060 | 0.073 |
(sin θ/λ)max (Å−1) | 0.595 | 0.595 | 0.617 |
|
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 reflections | 3167 | 3452 | 4906 |
No. of parameters | 329 | 363 | 466 |
No. of restraints | ? | 4 | 2 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.33, −0.34 | 0.46, −0.54 | 0.66, −0.59 |
Selected bond lengths (Å) for (C5ADP) topP1—O11 | 1.560 (1) | O31—N2v | 2.816 (2) |
P1—O21 | 1.504 (1) | O41—N2vi | 2.857 (2) |
P1—O31 | 1.498 (1) | P2—O12 | 1.556 (1) |
P1—O41 | 1.572 (1) | P2—O22 | 1.570 (1) |
O11—HO11 | 0.78 (2) | P2—O32 | 1.495 (1) |
O41—HO41 | 0.87 (2) | P2—O42 | 1.514 (1) |
N1—C11 | 1.488 (2) | O12—HO12 | 0.75 (2) |
C11—C21 | 1.514 (2) | O22—HO22 | 0.96 (2) |
C21—C31 | 1.519 (2) | N2—C12 | 1.484 (2) |
C31—C41 | 1.525 (3) | C12—C22 | 1.511 (2) |
C41—C51 | 1.526 (3) | C22—C32 | 1.520 (2) |
O11—O32i | 2.601 (2) | C32—C42 | 1.523 (3) |
O21—O22ii | 2.548 (2) | C42—C52 | 1.527 (3) |
O31—O12 | 2.591 (2) | O22—N1vii | 3.004 (2) |
O41—O42iii | 2.507 (1) | O32—N1viii | 2.797 (2) |
O21—N2iv | 2.859 (2) | O42—N1ix | 2.762 (2) |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) −x+1/2, y−1/2, −z+1/2; (vii) −x+2, −y+1, −z; (viii) −x+2, −y+1, −z+1; (ix) −x+3/2, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) for (C5ADP) top
D—H···A | D—H | D···A | D—H···A |
O11—HO11···O32i | 0.78 (2) | 2.600 (1) | 174 (2) |
O41—HO41···O42iii | 0.87 (2) | 2.507 (1) | 177 (2) |
O22—HO22···O21x | 0.96 (2) | 2.547 (2) | 171 (2) |
O12—HO12···O31 | 0.75 (2) | 2.591 (1) | 172 (2) |
N1—H1N1···O32viii | 0.88 (2) | 2.797 (2) | 170 (2) |
N1—H2N1···O42xi | 0.91 (2) | 2.761 (2) | 166 (2) |
N1—H3N1···O22vii | 0.82 (2) | 3.003 (2) | 156 (2) |
N2—H1N2···O21iv | 0.85 (2) | 2.859 (2) | 162 (2) |
N2—H2N2···O41xii | 0.87 (2) | 2.857 (2) | 162 (2) |
N2—H3N2···O31v | 0.91 (2) | 2.815 (2) | 161 (2) |
Symmetry codes: (i) x−1, y, z; (iii) x−1/2, −y+1/2, z−1/2; (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, z−1/2; (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) topP1—O11 | 1.556 (3) | N12—C12 | 1.486 (4) |
P1—O21 | 1.501 (3) | C12—C22 | 1.501 (4) |
P1—O31 | 1.505 (3) | C22—C32 | 1.523 (4) |
P1—O41 | 1.563 (3) | C32—C42 | 1.509 (5) |
O11—HO11 | 0.84 (2) | C42—C52 | 1.521 (5) |
O41—HO41 | 0.85 (1) | C52—C62 | 1.495 (6) |
P2—O12 | 1.554 (2) | O11—O32i | 2.610 (3) |
P2—O22 | 1.563 (2) | O21—O22ii | 2.550 (3) |
P2—O32 | 1.492 (2) | O31—O12 | 2.579 (3) |
P2—O42 | 1.515 (2) | O41—O42iii | 2.511 (3) |
N11—C11 | 1.484 (4) | O21—N2iv | 2.870 (3) |
C11—C21 | 1.501 (4) | O31—N2v | 2.813 (3) |
C21—C31 | 1.514 (5) | O41—N2vi | 2.850 (3) |
C31—C41 | 1.519 (5) | O22—N1v | 3.014 (3) |
C41—C51 | 1.515 (5) | O32—N1iv | 2.796 (3) |
C51—C61 | 1.505 (6) | O42—N1vi | 2.746 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vi) −x+1/2, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) for (C6ADP) top
D—H···A | D—H | D···A | D—H···A |
O11—HO11···O32i | 0.84 (2) | 2.610 (3) | 167 (3) |
O41—HO41···O42iii | 0.85 (1) | 2.511 (3) | 174 (3) |
O22—HO22···O21vii | 0.85 (1) | 2.551 (3) | 168 (3) |
O12—HO12···O31 | 0.85 (2) | 2.580 (3) | 172 (3) |
N1—H1N1···O32iv | 0.92 (3) | 2.796 (3) | 167 (3) |
N1—H2N1···O42viii | 0.88 (3) | 2.746 (3) | 163 (3) |
N1—H3N1···O22v | 0.79 (3) | 3.014 (3) | 155 (3) |
N2—H1N2···O21iv | 0.78 (3) | 2.870 (3) | 159 (3) |
N2—H2N2···O41viii | 0.93 (3) | 2.850 (3) | 158 (2) |
N2—H3N2···O31v | 0.95 (4) | 2.813 (3) | 168 (3) |
Symmetry codes: (i) x−1, y, z; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z; (vii) x+1/2, −y+1/2, z−1/2; (viii) −x+1/2, y+1/2, −z+1/2. |
Selected bond lengths (Å) for (C9ADP) topP1—O11 | 1.555 (2) | O22—HO22 | 0.80 (3) |
P1—O21 | 1.500 (1) | N1—C11 | 1.496 (3) |
P1—O31 | 1.493 (2) | C11—C21 | 1.492 (3) |
P1—O41 | 1.573 (2) | C21—C31 | 1.518 (4) |
O11—HO11 | 0.75 (4) | C31—C41 | 1.518 (4) |
O41—HO41 | 0.85 (3) | C41—C51 | 1.518 (4) |
P2—O12 | 1.553 (2) | C51—C61 | 1.525 (4) |
P2—O22 | 1.562 (2) | C61—C71 | 1.513 (4) |
P2—O32 | 1.494 (2) | C71—C81 | 1.510 (4) |
P2—O42 | 1.508 (2) | C81—C91 | 1.517 (4) |
O12—HO12 | 0.76 (2) | | |
Hydrogen-bond geometry (Å, º) for (C9ADP) top
D—H···A | D—H | D···A | D—H···A |
O11—HO11···O32i | 0.75 (4) | 2.604 (2) | 160 (4) |
O41—HO41···O42ii | 0.85 (3) | 2.535 (2) | 178 (4) |
O22—HO22···O21iii | 0.80 (3) | 2.544 (2) | 167 (3) |
O12—HO12···O31 | 0.76 (2) | 2.606 (2) | 169 (2) |
N1iv—H1N1···O32v | 0.82 (3) | 2.806 (3) | 167 (3) |
N1vi—H2N1···O42vii | 0.97 (3) | 2.739 (3) | 164 (3) |
N1—H3N1···O22 | 0.85 (3) | 3.047 (3) | 162 (3) |
N2—H1N2···O21v | 0.89 (2) | 2.888 (3) | 153 (2) |
N2—H2N2···O41vii | 0.79 (3) | 2.854 (3) | 161 (2) |
N2—H3N2···O31viii | 0.94 (3) | 2.837 (3) | 167 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) x+1, y+1, z+1; (v) −x+1, −y+1, −z+1; (vi) x, y−1, z; (vii) −x+1/2, y+1/2, −z+1/2; (viii) −x+1, −y+1, −z. |