The title compound, 2C
6H
18N
22+·P
4O
124−·2H
2O, has been synthesized at room temperature and studied by single-crystal X-ray diffraction. The asymmetric unit consists of two hexanediaminium cations, four PO
4 tetrahedra and two water molecules. The organic cations are linked to the cyclic P
4O
124− anions
via N—H
O hydrogen bonds to form two-dimensional layers, and are further linked by water molecules to form a three-dimensional network.
Supporting information
CCDC reference: 283989
Key indicators
- Single-crystal X-ray study
- T = 546 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.102
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 22
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
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: CAD-4 EXPRESS (Duisenberg, 1992; Macíček & Yordanov, 1992); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ATOMS for Windows (Dowty, 1995) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis(1,6-hexanediaminium) cyclotetraphosphate dihydrate
top
Crystal data top
2C6H18N22+·O12P44−·2H2O | F(000) = 1248 |
Mr = 588.36 | Dx = 1.530 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 9.676 (3) Å | θ = 10–15° |
b = 19.118 (6) Å | µ = 0.37 mm−1 |
c = 13.882 (3) Å | T = 546 K |
β = 95.90 (2)° | Plate, colourless |
V = 2554.2 (13) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.015 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.1° |
Graphite monochromator | h = 0→12 |
ω/2θ scans | k = 0→24 |
5890 measured reflections | l = −17→17 |
5566 independent reflections | 2 standard reflections every 60 min |
4554 reflections with I > 2σ(I) | intensity decay: 1.2% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0485P)2 + 2.0372P] where P = (Fo2 + 2Fc2)/3 |
5566 reflections | (Δ/σ)max < 0.001 |
457 parameters | Δρmax = 0.59 e Å−3 |
2 restraints | Δρmin = −0.38 e Å−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 | 0.37604 (5) | 0.22109 (3) | 0.17914 (4) | 0.02037 (12) | |
P2 | 0.26907 (5) | 0.08844 (3) | 0.09225 (4) | 0.01963 (12) | |
P3 | −0.02008 (5) | 0.13349 (3) | 0.11070 (4) | 0.02056 (12) | |
P4 | 0.08477 (5) | 0.27245 (3) | 0.17212 (4) | 0.02275 (13) | |
O11 | 0.48286 (16) | 0.23765 (9) | 0.11336 (12) | 0.0320 (3) | |
O21 | 0.40309 (15) | 0.24133 (8) | 0.28307 (10) | 0.0274 (3) | |
O12 | 0.27136 (15) | 0.12247 (8) | −0.00390 (10) | 0.0267 (3) | |
O22 | 0.32860 (16) | 0.01734 (7) | 0.10873 (12) | 0.0300 (3) | |
O13 | −0.13558 (16) | 0.09450 (9) | 0.14686 (12) | 0.0348 (4) | |
O23 | −0.03507 (15) | 0.16307 (8) | 0.01089 (10) | 0.0252 (3) | |
O14 | −0.00051 (18) | 0.30751 (8) | 0.09092 (12) | 0.0366 (4) | |
O24 | 0.10670 (17) | 0.30707 (8) | 0.26836 (11) | 0.0323 (4) | |
OL12 | 0.34189 (16) | 0.13870 (7) | 0.17637 (10) | 0.0266 (3) | |
OL14 | 0.23270 (15) | 0.25563 (7) | 0.13208 (10) | 0.0237 (3) | |
OL23 | 0.11458 (15) | 0.08340 (7) | 0.12375 (11) | 0.0253 (3) | |
OL34 | 0.02556 (15) | 0.19512 (8) | 0.18858 (10) | 0.0265 (3) | |
N1 | 0.2364 (2) | 0.73036 (10) | 0.04833 (15) | 0.0276 (4) | |
N2 | 0.3424 (2) | 0.40175 (11) | 0.34598 (15) | 0.0287 (4) | |
N3 | 0.9509 (2) | 0.42017 (11) | 0.36055 (15) | 0.0293 (4) | |
N4 | 0.8492 (2) | 0.75284 (11) | 0.08496 (16) | 0.0318 (4) | |
C11 | 0.3395 (2) | 0.67269 (12) | 0.06278 (18) | 0.0307 (5) | |
C21 | 0.2720 (3) | 0.60639 (13) | 0.0922 (2) | 0.0355 (5) | |
C31 | 0.3776 (3) | 0.54779 (12) | 0.11740 (19) | 0.0360 (5) | |
C41 | 0.3089 (3) | 0.48172 (14) | 0.1505 (2) | 0.0393 (6) | |
C51 | 0.4115 (3) | 0.42320 (14) | 0.18039 (19) | 0.0410 (6) | |
C61 | 0.4597 (3) | 0.41940 (13) | 0.28756 (18) | 0.0338 (5) | |
C12 | 0.8576 (3) | 0.46014 (15) | 0.2882 (2) | 0.0372 (5) | |
C22 | 0.9334 (3) | 0.47839 (15) | 0.2014 (2) | 0.0412 (6) | |
C32 | 0.8463 (4) | 0.52106 (17) | 0.1251 (2) | 0.0526 (7) | |
C42 | 0.8298 (3) | 0.59833 (15) | 0.1530 (2) | 0.0464 (6) | |
C52 | 0.7363 (3) | 0.63724 (17) | 0.0772 (2) | 0.0524 (7) | |
C62 | 0.7192 (3) | 0.71329 (15) | 0.0966 (2) | 0.0421 (6) | |
OW1 | 0.2171 (2) | 0.18866 (15) | 0.69922 (18) | 0.0721 (7) | |
OW2 | 0.6355 (2) | 0.14395 (11) | 0.01614 (14) | 0.0382 (4) | |
H1W1 | 0.1483 | 0.2182 | 0.6661 | 0.050* | |
H2W1 | 0.3020 | 0.1847 | 0.6655 | 0.050* | |
H1W2 | 0.576 (4) | 0.1651 (19) | 0.052 (3) | 0.066 (10)* | |
H2W2 | 0.688 (4) | 0.1238 (19) | 0.057 (3) | 0.059 (10)* | |
H1N1 | 0.200 (3) | 0.7365 (13) | 0.104 (2) | 0.032 (7)* | |
H2N1 | 0.279 (3) | 0.7694 (16) | 0.033 (2) | 0.043 (8)* | |
H3N1 | 0.166 (3) | 0.7192 (14) | 0.005 (2) | 0.037 (7)* | |
H1N2 | 0.375 (3) | 0.3858 (16) | 0.400 (2) | 0.048 (8)* | |
H2N2 | 0.295 (3) | 0.4378 (16) | 0.361 (2) | 0.041 (8)* | |
H3N2 | 0.285 (3) | 0.3680 (16) | 0.317 (2) | 0.044 (8)* | |
H1N3 | 0.906 (3) | 0.4072 (15) | 0.408 (2) | 0.047 (8)* | |
H2N3 | 0.987 (3) | 0.3815 (16) | 0.333 (2) | 0.041 (8)* | |
H3N3 | 1.021 (3) | 0.4500 (18) | 0.388 (2) | 0.055 (9)* | |
H1N4 | 0.911 (3) | 0.7501 (16) | 0.136 (2) | 0.043 (8)* | |
H2N4 | 0.896 (4) | 0.7347 (18) | 0.032 (3) | 0.061 (10)* | |
H3N4 | 0.831 (3) | 0.7952 (19) | 0.075 (2) | 0.055 (9)* | |
H111 | 0.381 (3) | 0.6662 (15) | 0.007 (2) | 0.043 (8)* | |
H211 | 0.416 (3) | 0.6881 (15) | 0.111 (2) | 0.045 (8)* | |
H121 | 0.203 (3) | 0.5915 (13) | 0.0431 (19) | 0.028 (6)* | |
H221 | 0.220 (3) | 0.6151 (16) | 0.149 (2) | 0.055 (9)* | |
H131 | 0.422 (3) | 0.5356 (14) | 0.056 (2) | 0.038 (7)* | |
H231 | 0.452 (3) | 0.5610 (17) | 0.173 (2) | 0.055 (9)* | |
H141 | 0.265 (3) | 0.4969 (18) | 0.210 (3) | 0.065 (10)* | |
H241 | 0.238 (3) | 0.4669 (17) | 0.094 (2) | 0.059 (9)* | |
H151 | 0.497 (3) | 0.4291 (16) | 0.146 (2) | 0.053 (9)* | |
H251 | 0.366 (3) | 0.3770 (18) | 0.161 (2) | 0.063 (10)* | |
H161 | 0.532 (3) | 0.3839 (16) | 0.302 (2) | 0.044 (8)* | |
H261 | 0.501 (3) | 0.4627 (17) | 0.311 (2) | 0.052 (9)* | |
H112 | 0.826 (3) | 0.5011 (17) | 0.321 (2) | 0.055 (9)* | |
H212 | 0.782 (3) | 0.4334 (15) | 0.272 (2) | 0.042 (8)* | |
H122 | 1.018 (4) | 0.5090 (19) | 0.224 (2) | 0.068 (10)* | |
H222 | 0.959 (4) | 0.431 (2) | 0.169 (3) | 0.079 (12)* | |
H132 | 0.890 (4) | 0.512 (2) | 0.060 (3) | 0.093 (13)* | |
H232 | 0.758 (4) | 0.4961 (18) | 0.119 (2) | 0.065 (10)* | |
H142 | 0.922 (3) | 0.6219 (17) | 0.164 (2) | 0.055 (9)* | |
H242 | 0.782 (4) | 0.601 (2) | 0.214 (3) | 0.094 (14)* | |
H152 | 0.780 (3) | 0.6342 (17) | 0.0211 (14) | 0.050* | |
H252 | 0.6495 (17) | 0.6170 (15) | 0.068 (2) | 0.050* | |
H162 | 0.698 (3) | 0.7191 (16) | 0.161 (2) | 0.052 (9)* | |
H262 | 0.645 (3) | 0.7338 (16) | 0.046 (2) | 0.054 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0210 (2) | 0.0204 (3) | 0.0192 (2) | −0.00141 (19) | −0.00022 (18) | −0.00183 (19) |
P2 | 0.0221 (2) | 0.0159 (2) | 0.0207 (2) | 0.00216 (18) | 0.00119 (18) | −0.00013 (18) |
P3 | 0.0191 (2) | 0.0207 (2) | 0.0215 (2) | −0.00121 (19) | 0.00025 (18) | 0.00067 (19) |
P4 | 0.0249 (3) | 0.0201 (3) | 0.0217 (3) | 0.0053 (2) | −0.00470 (19) | −0.00561 (19) |
O11 | 0.0303 (8) | 0.0336 (8) | 0.0334 (8) | −0.0043 (7) | 0.0096 (7) | −0.0013 (7) |
O21 | 0.0264 (7) | 0.0320 (8) | 0.0223 (7) | −0.0018 (6) | −0.0041 (6) | −0.0054 (6) |
O12 | 0.0319 (8) | 0.0276 (8) | 0.0212 (7) | 0.0031 (6) | 0.0053 (6) | 0.0022 (6) |
O22 | 0.0313 (8) | 0.0184 (7) | 0.0398 (9) | 0.0060 (6) | 0.0014 (7) | 0.0006 (6) |
O13 | 0.0257 (8) | 0.0367 (9) | 0.0425 (10) | −0.0066 (7) | 0.0063 (7) | 0.0067 (7) |
O23 | 0.0274 (7) | 0.0257 (7) | 0.0211 (7) | −0.0001 (6) | −0.0042 (6) | 0.0005 (6) |
O14 | 0.0415 (9) | 0.0243 (8) | 0.0393 (9) | 0.0084 (7) | −0.0178 (7) | −0.0019 (7) |
O24 | 0.0352 (8) | 0.0328 (8) | 0.0276 (8) | 0.0056 (7) | −0.0027 (6) | −0.0149 (7) |
OL12 | 0.0338 (8) | 0.0203 (7) | 0.0241 (7) | −0.0022 (6) | −0.0045 (6) | −0.0001 (6) |
OL14 | 0.0254 (7) | 0.0258 (7) | 0.0191 (7) | 0.0024 (6) | −0.0015 (5) | −0.0006 (6) |
OL23 | 0.0233 (7) | 0.0239 (7) | 0.0289 (8) | 0.0021 (6) | 0.0037 (6) | 0.0054 (6) |
OL34 | 0.0313 (8) | 0.0271 (8) | 0.0208 (7) | −0.0021 (6) | 0.0011 (6) | −0.0037 (6) |
N1 | 0.0300 (10) | 0.0251 (10) | 0.0271 (10) | 0.0048 (8) | 0.0004 (8) | 0.0025 (8) |
N2 | 0.0361 (10) | 0.0235 (10) | 0.0252 (10) | 0.0042 (8) | −0.0032 (8) | 0.0020 (8) |
N3 | 0.0291 (10) | 0.0278 (10) | 0.0315 (10) | −0.0018 (8) | 0.0049 (8) | 0.0025 (8) |
N4 | 0.0328 (11) | 0.0291 (11) | 0.0313 (10) | −0.0038 (8) | −0.0066 (9) | 0.0078 (8) |
C11 | 0.0313 (12) | 0.0291 (11) | 0.0317 (12) | 0.0091 (9) | 0.0032 (10) | 0.0040 (9) |
C21 | 0.0402 (13) | 0.0289 (12) | 0.0380 (13) | 0.0051 (10) | 0.0065 (11) | 0.0049 (10) |
C31 | 0.0431 (14) | 0.0274 (12) | 0.0381 (13) | 0.0054 (10) | 0.0066 (11) | 0.0058 (10) |
C41 | 0.0489 (15) | 0.0340 (13) | 0.0348 (13) | 0.0035 (11) | 0.0035 (11) | 0.0055 (10) |
C51 | 0.0591 (17) | 0.0303 (13) | 0.0353 (13) | 0.0073 (12) | 0.0130 (12) | 0.0043 (10) |
C61 | 0.0361 (12) | 0.0274 (12) | 0.0377 (13) | 0.0044 (10) | 0.0029 (10) | 0.0041 (10) |
C12 | 0.0320 (12) | 0.0387 (13) | 0.0402 (13) | 0.0051 (11) | 0.0012 (10) | 0.0068 (11) |
C22 | 0.0500 (16) | 0.0365 (14) | 0.0374 (13) | 0.0073 (12) | 0.0063 (11) | 0.0033 (11) |
C32 | 0.070 (2) | 0.0463 (17) | 0.0391 (15) | 0.0032 (15) | −0.0036 (14) | 0.0055 (13) |
C42 | 0.0554 (17) | 0.0400 (15) | 0.0428 (15) | 0.0035 (13) | 0.0011 (13) | 0.0015 (12) |
C52 | 0.0480 (16) | 0.0464 (16) | 0.0604 (19) | −0.0098 (13) | −0.0067 (14) | 0.0080 (14) |
C62 | 0.0352 (13) | 0.0451 (15) | 0.0459 (15) | −0.0064 (11) | 0.0042 (11) | 0.0106 (12) |
OW1 | 0.0490 (13) | 0.099 (2) | 0.0683 (15) | 0.0107 (13) | 0.0046 (11) | 0.0250 (14) |
OW2 | 0.0323 (9) | 0.0447 (10) | 0.0376 (10) | 0.0040 (8) | 0.0033 (8) | −0.0019 (8) |
Geometric parameters (Å, º) top
P1—O11 | 1.482 (2) | C21—C31 | 1.532 (3) |
P1—O21 | 1.491 (2) | C21—H121 | 0.94 (3) |
P1—OL12 | 1.609 (2) | C21—H221 | 1.00 (3) |
P1—OL14 | 1.613 (2) | C31—C41 | 1.520 (4) |
P2—O22 | 1.485 (2) | C31—H131 | 1.03 (3) |
P2—O12 | 1.487 (2) | C31—H231 | 1.03 (3) |
P2—OL23 | 1.603 (2) | C41—C51 | 1.524 (4) |
P2—OL12 | 1.617 (2) | C41—H141 | 1.01 (3) |
P3—O13 | 1.474 (2) | C41—H241 | 1.03 (3) |
P3—O23 | 1.490 (2) | C51—C61 | 1.514 (4) |
P3—OL23 | 1.612 (2) | C51—H151 | 1.00 (3) |
P3—OL34 | 1.629 (2) | C51—H251 | 1.01 (3) |
P4—O24 | 1.487 (2) | C61—H161 | 0.98 (3) |
P4—O14 | 1.486 (2) | C61—H261 | 0.96 (3) |
P4—OL34 | 1.610 (2) | C12—C22 | 1.514 (4) |
P4—OL14 | 1.620 (2) | C12—H112 | 0.97 (3) |
N1—C11 | 1.487 (3) | C12—H212 | 0.90 (3) |
N1—H1N1 | 0.89 (3) | C22—C32 | 1.521 (4) |
N1—H2N1 | 0.89 (3) | C22—H122 | 1.03 (4) |
N1—H3N1 | 0.89 (3) | C22—H222 | 1.04 (4) |
N2—C61 | 1.499 (3) | C32—C42 | 1.540 (4) |
N2—H1N2 | 0.84 (3) | C32—H132 | 1.05 (4) |
N2—H2N2 | 0.86 (3) | C32—H232 | 0.97 (4) |
N2—H3N2 | 0.92 (3) | C42—C52 | 1.511 (4) |
N3—C12 | 1.491 (3) | C42—H142 | 1.00 (3) |
N3—H1N3 | 0.87 (3) | C42—H242 | 1.01 (4) |
N3—H2N3 | 0.91 (3) | C52—C62 | 1.491 (4) |
N3—H3N3 | 0.94 (3) | C52—H152 | 0.92 (1) |
N4—C62 | 1.491 (3) | C52—H252 | 0.92 (1) |
N4—H1N4 | 0.88 (3) | C62—H162 | 0.94 (3) |
N4—H2N4 | 0.97 (4) | C62—H262 | 1.03 (3) |
N4—H3N4 | 0.84 (4) | OW1—H1W1 | 0.95 |
C11—C21 | 1.501 (3) | OW1—H2W1 | 0.99 |
C11—H111 | 0.92 (3) | OW2—H1W2 | 0.89 (4) |
C11—H211 | 0.99 (3) | OW2—H2W2 | 0.81 (4) |
| | | |
O11—P1—O21 | 118.48 (9) | H121—C21—H221 | 104 (2) |
O11—P1—OL12 | 110.42 (9) | C41—C31—C21 | 112.0 (2) |
O21—P1—OL12 | 107.00 (8) | C41—C31—H131 | 107 (2) |
O11—P1—OL14 | 106.75 (9) | C21—C31—H131 | 108 (2) |
O21—P1—OL14 | 110.11 (8) | C41—C31—H231 | 106 (2) |
OL12—P1—OL14 | 103.02 (8) | C21—C31—H231 | 113 (2) |
O22—P2—O12 | 119.84 (9) | H131—C31—H231 | 111 (2) |
O22—P2—OL23 | 105.12 (8) | C31—C41—C51 | 113.6 (2) |
O12—P2—OL23 | 111.81 (8) | C31—C41—H141 | 104 (2) |
O22—P2—OL12 | 107.42 (9) | C51—C41—H141 | 108 (2) |
O12—P2—OL12 | 110.03 (9) | C31—C41—H241 | 106 (2) |
OL23—P2—OL12 | 100.84 (8) | C51—C41—H241 | 112 (2) |
O13—P3—O23 | 120.27 (9) | H141—C41—H241 | 114 (3) |
O13—P3—OL23 | 107.08 (9) | C61—C51—C41 | 115.4 (2) |
O23—P3—OL23 | 109.28 (8) | C61—C51—H151 | 107 (2) |
O13—P3—OL34 | 107.65 (9) | C41—C51—H151 | 109 (2) |
O23—P3—OL34 | 109.67 (8) | C61—C51—H251 | 107 (2) |
OL23—P3—OL34 | 101.20 (8) | C41—C51—H251 | 108 (2) |
O24—P4—O14 | 119.9 (1) | H151—C51—H251 | 109 (3) |
O24—P4—OL34 | 107.53 (9) | N2—C61—C51 | 111.6 (2) |
O14—P4—OL34 | 110.11 (9) | N2—C61—H161 | 107 (2) |
O24—P4—OL14 | 110.32 (9) | C51—C61—H161 | 112 (2) |
O14—P4—OL14 | 105.69 (9) | N2—C61—H261 | 109 (2) |
OL34—P4—OL14 | 101.90 (8) | C51—C61—H261 | 111 (2) |
P1—OL12—P2 | 132.2 (1) | H161—C61—H261 | 105 (2) |
P1—OL14—P4 | 134.09 (9) | N3—C12—C22 | 110.2 (2) |
P2—OL23—P3 | 134.4 (1) | N3—C12—H112 | 107 (2) |
P4—OL34—P3 | 130.2 (1) | C22—C12—H112 | 113 (2) |
C11—N1—H1N1 | 108 (2) | N3—C12—H212 | 107 (2) |
C11—N1—H2N1 | 109 (2) | C22—C12—H212 | 112 (2) |
H1N1—N1—H2N1 | 109 (2) | H112—C12—H212 | 107 (3) |
C11—N1—H3N1 | 112 (2) | C12—C22—C32 | 113.5 (3) |
H1N1—N1—H3N1 | 106 (2) | C12—C22—H122 | 109 (2) |
H2N1—N1—H3N1 | 113 (3) | C32—C22—H122 | 106 (2) |
C61—N2—H1N2 | 109 (2) | C12—C22—H222 | 107 (2) |
C61—N2—H2N2 | 113 (2) | C32—C22—H222 | 108 (2) |
H1N2—N2—H2N2 | 104 (3) | H122—C22—H222 | 114 (3) |
C61—N2—H3N2 | 112 (2) | C22—C32—C42 | 113.8 (3) |
H1N2—N2—H3N2 | 107 (3) | C22—C32—H132 | 106 (2) |
H2N2—N2—H3N2 | 111 (3) | C42—C32—H132 | 116 (2) |
C12—N3—H1N3 | 110 (2) | C22—C32—H232 | 102 (2) |
C12—N3—H2N3 | 111 (2) | C42—C32—H232 | 112 (2) |
H1N3—N3—H2N3 | 109 (3) | H132—C32—H232 | 106 (3) |
C12—N3—H3N3 | 109 (2) | C52—C42—C32 | 111.5 (3) |
H1N3—N3—H3N3 | 105 (3) | C52—C42—H142 | 110 (2) |
H2N3—N3—H3N3 | 112 (3) | C32—C42—H142 | 111 (2) |
C62—N4—H1N4 | 113 (2) | C52—C42—H242 | 105 (2) |
C62—N4—H2N4 | 112 (2) | C32—C42—H242 | 109 (2) |
H1N4—N4—H2N4 | 105 (3) | H142—C42—H242 | 109 (3) |
C62—N4—H3N4 | 110 (2) | C62—C52—C42 | 115.1 (3) |
H1N4—N4—H3N4 | 108 (3) | C62—C52—H152 | 106 (2) |
H2N4—N4—H3N4 | 109 (3) | C42—C52—H152 | 105 (2) |
N1—C11—C21 | 111.0 (2) | C62—C52—H252 | 108 (2) |
N1—C11—H111 | 109 (2) | C42—C52—H252 | 111 (2) |
C21—C11—H111 | 111 (2) | H152—C52—H252 | 110 (3) |
N1—C11—H211 | 109 (2) | C52—C62—N4 | 111.4 (2) |
C21—C11—H211 | 113 (2) | C52—C62—H162 | 109 (2) |
H111—C11—H211 | 105 (2) | N4—C62—H162 | 108 (2) |
C11—C21—C31 | 112.4 (2) | C52—C62—H262 | 109 (2) |
C11—C21—H121 | 111 (2) | N4—C62—H262 | 106 (2) |
C31—C21—H121 | 110 (2) | H162—C62—H262 | 113 (3) |
C11—C21—H221 | 110 (2) | H1W1—OW1—H2W1 | 113 |
C31—C21—H221 | 109 (2) | H1W2—OW2—H2W2 | 102 (3) |
| | | |
O11—P1—OL12—P2 | −66.84 (16) | OL34—P3—OL23—P2 | −73.86 (15) |
O21—P1—OL12—P2 | 162.93 (13) | O24—P4—OL34—P3 | 178.97 (12) |
OL14—P1—OL12—P2 | 46.84 (15) | O14—P4—OL34—P3 | 46.79 (16) |
O22—P2—OL12—P1 | 150.65 (13) | OL14—P4—OL34—P3 | −65.01 (13) |
O12—P2—OL12—P1 | 18.62 (16) | O13—P3—OL34—P4 | −147.01 (12) |
OL23—P2—OL12—P1 | −99.57 (14) | O23—P3—OL34—P4 | −14.52 (15) |
O11—P1—OL14—P4 | −165.27 (13) | OL23—P3—OL34—P4 | 100.83 (13) |
O21—P1—OL14—P4 | −35.45 (16) | N1—C11—C21—C31 | −174.3 (2) |
OL12—P1—OL14—P4 | 78.39 (14) | C11—C21—C31—C41 | 178.0 (2) |
O24—P4—OL14—P1 | 46.85 (16) | C21—C31—C41—C51 | −177.5 (2) |
O14—P4—OL14—P1 | 177.79 (12) | C31—C41—C51—C61 | 94.5 (3) |
OL34—P4—OL14—P1 | −67.12 (14) | C41—C51—C61—N2 | 65.1 (3) |
O22—P2—OL23—P3 | −167.97 (13) | N3—C12—C22—C32 | −178.5 (2) |
O12—P2—OL23—P3 | −36.42 (17) | C12—C22—C32—C42 | 75.4 (4) |
OL12—P2—OL23—P3 | 80.47 (15) | C22—C32—C42—C52 | −177.0 (3) |
O13—P3—OL23—P2 | 173.55 (13) | C32—C42—C52—C62 | −177.6 (3) |
O23—P3—OL23—P2 | 41.79 (16) | C42—C52—C62—N4 | 70.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
OW1—H1W1···O11i | 0.95 | 1.890 | 2.826 (3) | 166.5 (2) |
OW1—H2W1···O14ii | 0.99 | 2.270 | 3.252 (4) | 171.8 (2) |
OW2—H1W2···O11 | 0.90 (4) | 1.90 (4) | 2.760 (3) | 160 (4) |
OW2—H2W2···O13iii | 0.81 (4) | 2.09 (4) | 2.875 (3) | 163 (4) |
N1—H1N1···O21iv | 0.89 (3) | 1.95 (3) | 2.827 (3) | 171 (3) |
N1—H2N1···OW2v | 0.89 (4) | 2.00 (4) | 2.888 (3) | 173 (3) |
N1—H3N1···O14vi | 0.89 (3) | 2.03 (3) | 2.926 (3) | 178 (3) |
N2—H1N2···O23ii | 0.84 (4) | 1.93 (4) | 2.761 (3) | 170 (3) |
N2—H2N2···O22iv | 0.86 (3) | 2.01 (4) | 2.869 (3) | 175 (3) |
N2—H3N2···O24 | 0.92 (4) | 2.13 (4) | 3.022 (3) | 163 (3) |
N3—H1N3···O12ii | 0.87 (4) | 1.95 (4) | 2.810 (3) | 168 (3) |
N3—H2N3···O24iii | 0.91 (3) | 2.10 (4) | 2.997 (3) | 168 (3) |
N3—H3N3···O22vii | 0.94 (4) | 1.94 (4) | 2.828 (3) | 157 (3) |
N4—H1N4···O21vii | 0.88 (4) | 2.03 (4) | 2.871 (3) | 160 (3) |
N4—H2N4···O14v | 0.97 (4) | 2.22 (4) | 3.189 (4) | 179 (3) |
N4—H3N4···O12v | 0.84 (4) | 2.05 (4) | 2.836 (3) | 155 (4) |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x+1, y, z; (iv) −x+1/2, y+1/2, −z+1/2; (v) −x+1, −y+1, −z; (vi) −x, −y+1, −z; (vii) −x+3/2, y+1/2, −z+1/2. |