Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023525/ng2263sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023525/ng2263Isup2.hkl |
CCDC reference: 650701
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.025
- wR factor = 0.056
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found Datablock: I
Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O4 .. C8 .. 2.90 Ang.
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Te1 - Mo1 .. 5.96 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Te1 - Mo3 .. 7.14 su PLAT414_ALERT_2_C Short Intra D-H..H-X H9A .. H17 .. 1.94 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N6 - H12 ... ? PLAT432_ALERT_2_C Short Inter X...Y Contact O9 .. C11 .. 2.94 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O12 .. 2.61 Ang.
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Te1 (6) 5.86 PLAT794_ALERT_5_G Check Predicted Bond Valency for Mo1 (6) 5.94 PLAT794_ALERT_5_G Check Predicted Bond Valency for Mo2 (6) 5.98 PLAT794_ALERT_5_G Check Predicted Bond Valency for Mo3 (6) 5.99
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 4 ALERT type 5 Informative message, check
Similar structures have been reported, see: Chen et al. (2007); Li et al. (2005); Liu et al. (2004); Drewes et al. (2004); Gao et al. (2006). For the synthesis of the [Te^VI^Mo^VI^~6Õ~24~]^6-^ polyanion see Saito (1994).
A mixture of Na6[TeVIMoVI6O24]6-.22H2O (0.32 g, 0.2 mmol) (Saito, 1994)) and ABOB (0.21 g, 1.2 mmol) in water (30 ml) treated with dilute hydrochloric acid to pH 5–6. The solution was stirred for 2 h. It was then filtered; the filtrate was set aside for the formation of crystals after two weeks; yield 65% based on Te.
The H atoms on water molecules, amine, and protonated imine groups were located in a difference Fourier map, and refined with distance restraints of with O–H = 0.85 Å, N–H = 0.90 Å and Uiso(H) = 1.2 Ueq(O,N). Those on C atoms are placed in calculated positions and refined in the riding model approximation with C–H = 0.97 Å and Uiso(H) = 1.2Ueq(C).
N-Amidino-4-morpholincarboxamidine (ABOB) is an effective broad-spectrum antiviral medicine to influenza, chickenpox and measles. In our chemical studies (Chen et al., 2007; Li et al., 2005; Liu et al., 2004), we found it is a versatile ligand capable of interacting with different types of polyanions. As a part of our ongoing work, we have investigated the reaction of ABOB and the Anderson type [TeVIMoVI6O24]6- polyanion to give a compound formulated as (H2ABOB)2(HABOB)2[TeVIMoVI6O24].4H2O (I).
The compound consists of [TeVIMoVI6O24]6-, protonated ABOB, and lattice water molecules. The three-dimensional supramolecular structure is formed by electrostatic forces and hydrogen bonding interactions among these components (Fig. 1). The [TeVIMoVI6O24]6- anion lies on an inversion center and is close to having D3 d symmetry. It is made up of six MoO6 octahedra surrounding one TeO6 octahedron by entirely edge-shared contacts; bond lengths and angles are in accordance with those of reported examples (Drewes et al., 2004; Gao et al., 2006) The diprotonated ABOB acquires two protons with its two imine groups (N2, N4). The monoprotonated ABOB acquires two protons with two imine groups (N6, N9) as well but loses one proton on the third imine groups (N8). Electrostatic forces and hydrogen bonding interactions result in a three-dimensional supramolecular structure (Figure 2, Figure 3). The hydrogen-bond donors are the protonated imines groups and water molecules whereas the acceptors are mostly the O atoms of the Anderson type polyanion.
Similar structures have been reported, see: Chen et al. (2007); Li et al. (2005); Liu et al. (2004); Drewes et al. (2004); Gao et al. (2006). For the synthesis of the [Te^VI^Mo^VI^~6Õ~24~]^6-^ polyanion see Saito (1994).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Bruker, 2001).
(C6H15N5O)2(C6H14N5O)2[TeMo6O24].4H2O | F(000) = 1820 |
Mr = 1850.21 | Dx = 2.205 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 875 reflections |
a = 15.722 (3) Å | θ = 3.1–25.0° |
b = 9.2364 (18) Å | µ = 1.93 mm−1 |
c = 19.256 (4) Å | T = 298 K |
β = 94.67 (3)° | Block, white |
V = 2787.0 (10) Å3 | 0.24 × 0.24 × 0.22 mm |
Z = 2 |
Rigaku R-AXIS RAPID IP diffractometer | 4883 independent reflections |
Radiation source: fine-focus sealed tube | 4465 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 0 pixels mm-1 | θmax = 25.0°, θmin = 3.1° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −10→10 |
Tmin = 0.643, Tmax = 0.657 | l = −22→22 |
20771 measured reflections |
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.056 | w = 1/[σ2(Fo2) + (0.0189P)2 + 3.249P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.002 |
4883 reflections | Δρmax = 0.63 e Å−3 |
377 parameters | Δρmin = −0.86 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00488 (13) |
(C6H15N5O)2(C6H14N5O)2[TeMo6O24].4H2O | V = 2787.0 (10) Å3 |
Mr = 1850.21 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.722 (3) Å | µ = 1.93 mm−1 |
b = 9.2364 (18) Å | T = 298 K |
c = 19.256 (4) Å | 0.24 × 0.24 × 0.22 mm |
β = 94.67 (3)° |
Rigaku R-AXIS RAPID IP diffractometer | 4883 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4465 reflections with I > 2σ(I) |
Tmin = 0.643, Tmax = 0.657 | Rint = 0.030 |
20771 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.63 e Å−3 |
4883 reflections | Δρmin = −0.86 e Å−3 |
377 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Te1 | 1.0000 | 1.0000 | 0.0000 | 0.01336 (7) | |
Mo1 | 0.840705 (14) | 0.97463 (2) | −0.121498 (12) | 0.01725 (8) | |
Mo2 | 0.962462 (15) | 1.03579 (3) | 0.163987 (12) | 0.01902 (8) | |
Mo3 | 0.804183 (14) | 1.00883 (2) | 0.045455 (12) | 0.01829 (8) | |
O1 | 1.06718 (11) | 0.87503 (19) | −0.05424 (9) | 0.0177 (4) | |
O2 | 0.89805 (11) | 0.88611 (19) | −0.01551 (9) | 0.0166 (4) | |
O3 | 0.96442 (11) | 1.09343 (19) | −0.08720 (9) | 0.0176 (4) | |
O4 | 0.91282 (14) | 1.1756 (2) | 0.20215 (11) | 0.0333 (5) | |
O5 | 0.92935 (12) | 0.8616 (2) | −0.15719 (9) | 0.0212 (4) | |
O6 | 0.75632 (13) | 1.1543 (2) | 0.08024 (11) | 0.0330 (5) | |
O7 | 0.76252 (12) | 0.8424 (2) | −0.12693 (11) | 0.0276 (5) | |
O8 | 0.72660 (13) | 0.8813 (2) | 0.02944 (11) | 0.0323 (5) | |
O9 | 0.99343 (13) | 0.9194 (2) | 0.22975 (10) | 0.0296 (5) | |
O10 | 0.79802 (11) | 1.09461 (19) | −0.04971 (9) | 0.0192 (4) | |
O11 | 0.81680 (13) | 1.0896 (2) | −0.18973 (10) | 0.0293 (5) | |
O12 | 0.86502 (12) | 0.9258 (2) | 0.12556 (9) | 0.0219 (4) | |
O13 | 0.51701 (15) | 0.1569 (3) | −0.10142 (15) | 0.0582 (8) | |
O14 | 0.70371 (14) | 1.0881 (2) | 0.31912 (13) | 0.0397 (6) | |
O1W | 0.96255 (14) | 0.6375 (2) | 0.11550 (12) | 0.0370 (5) | |
H1 | 0.9889 | 0.7141 | 0.1055 | 0.044* | |
H2 | 0.9140 | 0.6556 | 0.1301 | 0.044* | |
O2W | 1.07989 (17) | 0.4426 (3) | 0.18435 (15) | 0.0540 (7) | |
H3 | 1.0676 | 0.3607 | 0.1661 | 0.065* | |
H4 | 1.0434 | 0.4979 | 0.1629 | 0.065* | |
N1 | 0.83492 (18) | 0.6090 (3) | −0.03895 (14) | 0.0344 (6) | |
H5 | 0.8712 | 0.6705 | −0.0155 | 0.041* | |
H6 | 0.7979 | 0.6376 | −0.0744 | 0.041* | |
N2 | 0.90623 (15) | 0.4192 (3) | 0.01555 (13) | 0.0282 (6) | |
H7 | 0.9353 | 0.4823 | 0.0441 | 0.034* | |
H8 | 0.9136 | 0.3237 | 0.0232 | 0.034* | |
N3 | 0.79856 (16) | 0.3705 (3) | −0.06762 (13) | 0.0277 (6) | |
H9 | 0.8008 | 0.2776 | −0.0534 | 0.033* | |
N4 | 0.75224 (18) | 0.4803 (3) | −0.17227 (14) | 0.0354 (6) | |
H10 | 0.8071 | 0.5025 | −0.1774 | 0.042* | |
H11 | 0.7113 | 0.5017 | −0.2061 | 0.042* | |
N5 | 0.65933 (16) | 0.3408 (3) | −0.11197 (13) | 0.0300 (6) | |
N6 | 1.0938 (2) | 0.7734 (4) | 0.45693 (18) | 0.0577 (9) | |
H12 | 1.0669 | 0.7843 | 0.4961 | 0.069* | |
H13 | 1.1469 | 0.7363 | 0.4607 | 0.069* | |
N7 | 1.08581 (17) | 0.7464 (3) | 0.33860 (16) | 0.0453 (8) | |
H14 | 1.1380 | 0.7059 | 0.3425 | 0.054* | |
H15 | 1.0642 | 0.7675 | 0.2950 | 0.054* | |
N8 | 0.96948 (16) | 0.8341 (3) | 0.39610 (14) | 0.0358 (6) | |
N9 | 0.90343 (17) | 0.6720 (3) | 0.31506 (16) | 0.0418 (7) | |
H16 | 0.9432 | 0.6051 | 0.3279 | 0.050* | |
H17 | 0.8657 | 0.6575 | 0.2780 | 0.050* | |
N10 | 0.84324 (15) | 0.8936 (3) | 0.33528 (13) | 0.0263 (5) | |
C1 | 0.5878 (2) | 0.1522 (4) | −0.05053 (19) | 0.0438 (9) | |
H1A | 0.6283 | 0.0799 | −0.0637 | 0.053* | |
H1B | 0.5684 | 0.1246 | −0.0058 | 0.053* | |
C2 | 0.5475 (2) | 0.1889 (5) | −0.1672 (2) | 0.0537 (10) | |
H2A | 0.4998 | 0.1879 | −0.2026 | 0.064* | |
H2B | 0.5872 | 0.1140 | −0.1788 | 0.064* | |
C3 | 0.5913 (2) | 0.3336 (4) | −0.16842 (18) | 0.0416 (8) | |
H3A | 0.6151 | 0.3470 | −0.2129 | 0.050* | |
H3B | 0.5502 | 0.4103 | −0.1629 | 0.050* | |
C4 | 0.6308 (2) | 0.2974 (4) | −0.04428 (17) | 0.0381 (8) | |
H4A | 0.5912 | 0.3689 | −0.0288 | 0.046* | |
H4B | 0.6794 | 0.2925 | −0.0099 | 0.046* | |
C5 | 0.7344 (2) | 0.4006 (3) | −0.11897 (15) | 0.0263 (6) | |
C6 | 0.84770 (18) | 0.4686 (3) | −0.03086 (15) | 0.0228 (6) | |
C7 | 0.7724 (2) | 1.1139 (4) | 0.3706 (2) | 0.0452 (9) | |
H7A | 0.7575 | 1.0754 | 0.4149 | 0.054* | |
H7B | 0.7806 | 1.2175 | 0.3761 | 0.054* | |
C8 | 0.6910 (2) | 0.9357 (3) | 0.31187 (19) | 0.0371 (8) | |
H8A | 0.6423 | 0.9178 | 0.2788 | 0.045* | |
H8B | 0.6784 | 0.8954 | 0.3564 | 0.045* | |
C9 | 0.76780 (19) | 0.8614 (4) | 0.28752 (17) | 0.0320 (7) | |
H9A | 0.7582 | 0.7577 | 0.2858 | 0.038* | |
H9B | 0.7774 | 0.8942 | 0.2409 | 0.038* | |
C10 | 0.8540 (2) | 1.0472 (4) | 0.35268 (18) | 0.0367 (8) | |
H10A | 0.8746 | 1.0980 | 0.3133 | 0.044* | |
H10B | 0.8964 | 1.0573 | 0.3919 | 0.044* | |
C11 | 0.90742 (19) | 0.8001 (3) | 0.34730 (16) | 0.0288 (7) | |
C12 | 1.0479 (2) | 0.7821 (4) | 0.39541 (19) | 0.0372 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Te1 | 0.01484 (13) | 0.01183 (12) | 0.01295 (13) | −0.00084 (8) | −0.00163 (9) | 0.00035 (9) |
Mo1 | 0.01854 (13) | 0.01554 (13) | 0.01677 (13) | −0.00164 (9) | −0.00401 (9) | 0.00015 (9) |
Mo2 | 0.02178 (14) | 0.02072 (14) | 0.01437 (13) | −0.00030 (9) | 0.00025 (9) | −0.00023 (9) |
Mo3 | 0.01674 (13) | 0.01865 (13) | 0.01923 (13) | −0.00111 (9) | 0.00005 (9) | 0.00082 (9) |
O1 | 0.0194 (9) | 0.0156 (9) | 0.0179 (9) | 0.0014 (7) | 0.0009 (7) | −0.0018 (8) |
O2 | 0.0170 (9) | 0.0144 (9) | 0.0179 (9) | −0.0031 (7) | −0.0019 (7) | 0.0007 (7) |
O3 | 0.0196 (9) | 0.0168 (9) | 0.0157 (9) | −0.0010 (7) | −0.0036 (7) | 0.0028 (8) |
O4 | 0.0345 (12) | 0.0342 (12) | 0.0315 (11) | 0.0043 (9) | 0.0054 (9) | −0.0070 (10) |
O5 | 0.0244 (10) | 0.0188 (9) | 0.0201 (9) | −0.0027 (8) | −0.0005 (8) | −0.0035 (8) |
O6 | 0.0318 (12) | 0.0371 (12) | 0.0298 (11) | 0.0105 (9) | 0.0017 (9) | −0.0031 (10) |
O7 | 0.0233 (10) | 0.0250 (10) | 0.0334 (11) | −0.0050 (8) | −0.0051 (9) | −0.0030 (9) |
O8 | 0.0286 (12) | 0.0341 (12) | 0.0329 (11) | −0.0120 (9) | −0.0046 (9) | 0.0071 (10) |
O9 | 0.0335 (12) | 0.0330 (12) | 0.0216 (10) | −0.0047 (9) | −0.0028 (9) | 0.0083 (9) |
O10 | 0.0194 (10) | 0.0149 (9) | 0.0226 (9) | 0.0018 (7) | −0.0021 (7) | 0.0017 (8) |
O11 | 0.0361 (12) | 0.0257 (11) | 0.0245 (11) | 0.0008 (9) | −0.0077 (9) | 0.0050 (9) |
O12 | 0.0221 (10) | 0.0234 (10) | 0.0202 (10) | −0.0035 (8) | 0.0014 (8) | 0.0042 (8) |
O13 | 0.0313 (14) | 0.076 (2) | 0.0657 (18) | −0.0082 (13) | −0.0048 (12) | 0.0279 (16) |
O14 | 0.0301 (12) | 0.0254 (11) | 0.0622 (16) | 0.0041 (9) | −0.0047 (11) | 0.0019 (11) |
O1W | 0.0405 (13) | 0.0229 (11) | 0.0482 (14) | −0.0051 (9) | 0.0074 (11) | −0.0027 (11) |
O2W | 0.0557 (17) | 0.0388 (14) | 0.0658 (18) | −0.0077 (12) | −0.0047 (14) | 0.0036 (14) |
N1 | 0.0478 (17) | 0.0171 (12) | 0.0358 (15) | −0.0010 (11) | −0.0125 (12) | 0.0008 (11) |
N2 | 0.0320 (14) | 0.0203 (12) | 0.0307 (14) | −0.0021 (10) | −0.0074 (11) | 0.0000 (11) |
N3 | 0.0379 (15) | 0.0123 (11) | 0.0306 (13) | −0.0008 (10) | −0.0105 (11) | 0.0038 (10) |
N4 | 0.0389 (16) | 0.0341 (15) | 0.0312 (15) | −0.0047 (12) | −0.0085 (12) | 0.0095 (12) |
N5 | 0.0314 (14) | 0.0328 (14) | 0.0249 (13) | 0.0016 (11) | −0.0042 (11) | 0.0049 (11) |
N6 | 0.0385 (18) | 0.078 (2) | 0.053 (2) | 0.0157 (17) | −0.0173 (15) | 0.0055 (19) |
N7 | 0.0240 (15) | 0.060 (2) | 0.0519 (19) | 0.0129 (13) | 0.0017 (13) | 0.0115 (16) |
N8 | 0.0272 (14) | 0.0463 (17) | 0.0325 (14) | 0.0086 (12) | −0.0049 (11) | −0.0024 (13) |
N9 | 0.0308 (15) | 0.0335 (15) | 0.0598 (19) | 0.0085 (12) | −0.0045 (14) | −0.0079 (14) |
N10 | 0.0199 (12) | 0.0285 (13) | 0.0299 (13) | 0.0014 (10) | −0.0011 (10) | −0.0025 (11) |
C1 | 0.0363 (19) | 0.052 (2) | 0.043 (2) | 0.0019 (16) | 0.0027 (16) | 0.0171 (18) |
C2 | 0.041 (2) | 0.068 (3) | 0.049 (2) | −0.0111 (19) | −0.0164 (17) | 0.012 (2) |
C3 | 0.0325 (18) | 0.055 (2) | 0.0356 (18) | 0.0014 (16) | −0.0110 (14) | 0.0133 (17) |
C4 | 0.0416 (19) | 0.046 (2) | 0.0274 (17) | 0.0097 (15) | 0.0064 (14) | 0.0049 (16) |
C5 | 0.0373 (17) | 0.0163 (14) | 0.0239 (15) | 0.0037 (12) | −0.0062 (12) | 0.0000 (12) |
C6 | 0.0293 (15) | 0.0156 (13) | 0.0237 (14) | −0.0022 (11) | 0.0028 (12) | 0.0002 (12) |
C7 | 0.044 (2) | 0.0358 (19) | 0.056 (2) | 0.0023 (16) | 0.0007 (17) | −0.0128 (18) |
C8 | 0.0277 (17) | 0.0307 (17) | 0.052 (2) | 0.0008 (13) | −0.0016 (15) | 0.0033 (16) |
C9 | 0.0257 (16) | 0.0342 (17) | 0.0352 (17) | −0.0002 (13) | −0.0037 (13) | −0.0047 (15) |
C10 | 0.0341 (18) | 0.0343 (18) | 0.0407 (19) | −0.0018 (14) | −0.0024 (14) | −0.0083 (15) |
C11 | 0.0226 (15) | 0.0345 (17) | 0.0295 (16) | 0.0014 (12) | 0.0040 (12) | 0.0045 (14) |
C12 | 0.0279 (17) | 0.0330 (17) | 0.049 (2) | 0.0014 (14) | −0.0065 (15) | 0.0101 (16) |
Te1—O2 | 1.9202 (17) | N3—C5 | 1.382 (4) |
Te1—O2i | 1.9202 (17) | N3—H9 | 0.9000 |
Te1—O1 | 1.9283 (17) | N4—C5 | 1.312 (4) |
Te1—O1i | 1.9283 (17) | N4—H10 | 0.8998 |
Te1—O3 | 1.9298 (17) | N4—H11 | 0.9000 |
Te1—O3i | 1.9298 (17) | N5—C5 | 1.320 (4) |
Mo1—O11 | 1.7075 (19) | N5—C3 | 1.464 (4) |
Mo1—O7 | 1.7298 (19) | N5—C4 | 1.468 (4) |
Mo1—O5 | 1.9131 (19) | N6—C12 | 1.339 (4) |
Mo1—O10 | 1.9339 (18) | N6—H12 | 0.9001 |
Mo1—O3 | 2.2834 (18) | N6—H13 | 0.9000 |
Mo1—O2 | 2.3123 (18) | N7—C12 | 1.329 (4) |
Mo2—O9 | 1.702 (2) | N7—H14 | 0.9001 |
Mo2—O4 | 1.706 (2) | N7—H15 | 0.9001 |
Mo2—O12 | 1.9343 (19) | N8—C12 | 1.324 (4) |
Mo2—O5i | 1.9606 (19) | N8—C11 | 1.336 (4) |
Mo2—O1i | 2.2806 (18) | N9—C11 | 1.335 (4) |
Mo2—O3i | 2.2823 (18) | N9—H16 | 0.8999 |
Mo3—O6 | 1.704 (2) | N9—H17 | 0.9000 |
Mo3—O8 | 1.706 (2) | N10—C11 | 1.334 (4) |
Mo3—O12 | 1.9084 (19) | N10—C10 | 1.464 (4) |
Mo3—O10 | 1.9916 (18) | N10—C9 | 1.471 (4) |
Mo3—O2 | 2.2634 (18) | C1—C4 | 1.503 (5) |
Mo3—O1i | 2.2835 (18) | C1—H1A | 0.9700 |
O1—Mo2i | 2.2806 (18) | C1—H1B | 0.9700 |
O1—Mo3i | 2.2835 (18) | C2—C3 | 1.504 (5) |
O3—Mo2i | 2.2823 (18) | C2—H2A | 0.9700 |
O5—Mo2i | 1.9606 (18) | C2—H2B | 0.9700 |
O13—C2 | 1.422 (5) | C3—H3A | 0.9700 |
O13—C1 | 1.422 (4) | C3—H3B | 0.9700 |
O14—C7 | 1.426 (4) | C4—H4A | 0.9700 |
O14—C8 | 1.427 (4) | C4—H4B | 0.9700 |
O1W—H1 | 0.8500 | C7—C10 | 1.488 (5) |
O1W—H2 | 0.8500 | C7—H7A | 0.9700 |
O2W—H3 | 0.8499 | C7—H7B | 0.9700 |
O2W—H4 | 0.8500 | C8—C9 | 1.497 (4) |
N1—C6 | 1.319 (4) | C8—H8A | 0.9700 |
N1—H5 | 0.8999 | C8—H8B | 0.9700 |
N1—H6 | 0.9001 | C9—H9A | 0.9700 |
N2—C6 | 1.311 (4) | C9—H9B | 0.9700 |
N2—H7 | 0.9001 | C10—H10A | 0.9700 |
N2—H8 | 0.9000 | C10—H10B | 0.9700 |
N3—C6 | 1.353 (4) | ||
O2—Te1—O2i | 180.0 | C6—N3—C5 | 126.3 (2) |
O2—Te1—O1 | 94.30 (8) | C6—N3—H9 | 118.2 |
O2i—Te1—O1 | 85.70 (8) | C5—N3—H9 | 114.6 |
O2—Te1—O1i | 85.70 (8) | C5—N4—H10 | 118.8 |
O2i—Te1—O1i | 94.30 (8) | C5—N4—H11 | 120.2 |
O1—Te1—O1i | 180.00 (8) | H10—N4—H11 | 120.5 |
O2—Te1—O3 | 86.01 (8) | C5—N5—C3 | 123.3 (3) |
O2i—Te1—O3 | 93.99 (8) | C5—N5—C4 | 123.1 (3) |
O1—Te1—O3 | 85.94 (8) | C3—N5—C4 | 112.9 (3) |
O1i—Te1—O3 | 94.06 (8) | C12—N6—H12 | 118.6 |
O2—Te1—O3i | 93.99 (8) | C12—N6—H13 | 121.6 |
O2i—Te1—O3i | 86.01 (8) | H12—N6—H13 | 118.1 |
O1—Te1—O3i | 94.06 (8) | C12—N7—H14 | 120.1 |
O1i—Te1—O3i | 85.94 (8) | C12—N7—H15 | 123.6 |
O3—Te1—O3i | 180.00 (10) | H14—N7—H15 | 116.1 |
O11—Mo1—O7 | 106.37 (10) | C12—N8—C11 | 122.3 (3) |
O11—Mo1—O5 | 100.61 (9) | C11—N9—H16 | 118.4 |
O7—Mo1—O5 | 97.36 (9) | C11—N9—H17 | 120.3 |
O11—Mo1—O10 | 97.24 (9) | H16—N9—H17 | 120.9 |
O7—Mo1—O10 | 99.29 (9) | C11—N10—C10 | 121.1 (3) |
O5—Mo1—O10 | 151.01 (8) | C11—N10—C9 | 122.5 (3) |
O11—Mo1—O3 | 93.01 (9) | C10—N10—C9 | 114.3 (2) |
O7—Mo1—O3 | 160.24 (8) | O13—C1—C4 | 110.4 (3) |
O5—Mo1—O3 | 74.79 (7) | O13—C1—H1A | 109.6 |
O10—Mo1—O3 | 81.66 (7) | C4—C1—H1A | 109.6 |
O11—Mo1—O2 | 160.86 (8) | O13—C1—H1B | 109.6 |
O7—Mo1—O2 | 91.60 (8) | C4—C1—H1B | 109.6 |
O5—Mo1—O2 | 83.17 (7) | H1A—C1—H1B | 108.1 |
O10—Mo1—O2 | 72.83 (7) | O13—C2—C3 | 112.7 (3) |
O3—Mo1—O2 | 69.69 (6) | O13—C2—H2A | 109.1 |
O9—Mo2—O4 | 105.72 (10) | C3—C2—H2A | 109.1 |
O9—Mo2—O12 | 97.04 (9) | O13—C2—H2B | 109.1 |
O4—Mo2—O12 | 100.74 (9) | C3—C2—H2B | 109.1 |
O9—Mo2—O5i | 99.08 (9) | H2A—C2—H2B | 107.8 |
O4—Mo2—O5i | 95.33 (9) | N5—C3—C2 | 109.7 (3) |
O12—Mo2—O5i | 153.20 (8) | N5—C3—H3A | 109.7 |
O9—Mo2—O1i | 160.41 (8) | C2—C3—H3A | 109.7 |
O4—Mo2—O1i | 93.42 (9) | N5—C3—H3B | 109.7 |
O12—Mo2—O1i | 74.90 (7) | C2—C3—H3B | 109.7 |
O5i—Mo2—O1i | 82.91 (7) | H3A—C3—H3B | 108.2 |
O9—Mo2—O3i | 91.31 (9) | N5—C4—C1 | 109.9 (3) |
O4—Mo2—O3i | 161.30 (9) | N5—C4—H4A | 109.7 |
O12—Mo2—O3i | 84.42 (7) | C1—C4—H4A | 109.7 |
O5i—Mo2—O3i | 73.98 (7) | N5—C4—H4B | 109.7 |
O1i—Mo2—O3i | 70.38 (6) | C1—C4—H4B | 109.7 |
O6—Mo3—O8 | 106.47 (11) | H4A—C4—H4B | 108.2 |
O6—Mo3—O12 | 101.97 (9) | N4—C5—N5 | 124.4 (3) |
O8—Mo3—O12 | 99.94 (9) | N4—C5—N3 | 118.8 (3) |
O6—Mo3—O10 | 93.33 (9) | N5—C5—N3 | 116.7 (3) |
O8—Mo3—O10 | 97.35 (9) | N2—C6—N1 | 121.0 (3) |
O12—Mo3—O10 | 152.52 (8) | N2—C6—N3 | 117.5 (3) |
O6—Mo3—O2 | 157.88 (9) | N1—C6—N3 | 121.4 (3) |
O8—Mo3—O2 | 92.71 (9) | O14—C7—C10 | 112.8 (3) |
O12—Mo3—O2 | 85.01 (7) | O14—C7—H7A | 109.0 |
O10—Mo3—O2 | 72.96 (7) | C10—C7—H7A | 109.0 |
O6—Mo3—O1i | 90.99 (9) | O14—C7—H7B | 109.0 |
O8—Mo3—O1i | 162.53 (9) | C10—C7—H7B | 109.0 |
O12—Mo3—O1i | 75.30 (7) | H7A—C7—H7B | 107.8 |
O10—Mo3—O1i | 81.82 (7) | O14—C8—C9 | 111.9 (3) |
O2—Mo3—O1i | 70.29 (6) | O14—C8—H8A | 109.2 |
Te1—O1—Mo2i | 101.89 (8) | C9—C8—H8A | 109.2 |
Te1—O1—Mo3i | 101.51 (8) | O14—C8—H8B | 109.2 |
Mo2i—O1—Mo3i | 90.68 (7) | C9—C8—H8B | 109.2 |
Te1—O2—Mo3 | 102.49 (8) | H8A—C8—H8B | 107.9 |
Te1—O2—Mo1 | 101.78 (8) | N10—C9—C8 | 110.0 (3) |
Mo3—O2—Mo1 | 93.26 (7) | N10—C9—H9A | 109.7 |
Te1—O3—Mo2i | 101.78 (8) | C8—C9—H9A | 109.7 |
Te1—O3—Mo1 | 102.51 (8) | N10—C9—H9B | 109.7 |
Mo2i—O3—Mo1 | 91.35 (6) | C8—C9—H9B | 109.7 |
Mo1—O5—Mo2i | 114.94 (9) | H9A—C9—H9B | 108.2 |
Mo1—O10—Mo3 | 115.85 (9) | N10—C10—C7 | 111.7 (3) |
Mo3—O12—Mo2 | 115.31 (9) | N10—C10—H10A | 109.3 |
C2—O13—C1 | 108.6 (3) | C7—C10—H10A | 109.3 |
C7—O14—C8 | 109.0 (2) | N10—C10—H10B | 109.3 |
H1—O1W—H2 | 112.3 | C7—C10—H10B | 109.3 |
H3—O2W—H4 | 102.2 | H10A—C10—H10B | 107.9 |
C6—N1—H5 | 118.5 | N10—C11—N9 | 119.1 (3) |
C6—N1—H6 | 117.5 | N10—C11—N8 | 118.0 (3) |
H5—N1—H6 | 122.6 | N9—C11—N8 | 122.6 (3) |
C6—N2—H7 | 119.0 | N8—C12—N7 | 125.3 (3) |
C6—N2—H8 | 121.8 | N8—C12—N6 | 116.6 (3) |
H7—N2—H8 | 118.8 | N7—C12—N6 | 117.9 (3) |
O2—Te1—O1—Mo2i | 86.08 (8) | O10—Mo1—O5—Mo2i | −56.2 (2) |
O2i—Te1—O1—Mo2i | −93.92 (8) | O3—Mo1—O5—Mo2i | −19.37 (8) |
O3—Te1—O1—Mo2i | 0.40 (7) | O2—Mo1—O5—Mo2i | −90.12 (10) |
O3i—Te1—O1—Mo2i | −179.60 (7) | O11—Mo1—O10—Mo3 | 177.24 (10) |
O2—Te1—O1—Mo3i | 179.25 (7) | O7—Mo1—O10—Mo3 | 69.26 (11) |
O2i—Te1—O1—Mo3i | −0.75 (7) | O5—Mo1—O10—Mo3 | −55.0 (2) |
O3—Te1—O1—Mo3i | 93.57 (8) | O3—Mo1—O10—Mo3 | −90.76 (10) |
O3i—Te1—O1—Mo3i | −86.43 (8) | O2—Mo1—O10—Mo3 | −19.54 (8) |
O1—Te1—O2—Mo3 | 179.24 (7) | O6—Mo3—O10—Mo1 | −177.72 (11) |
O1i—Te1—O2—Mo3 | −0.76 (7) | O8—Mo3—O10—Mo1 | −70.63 (12) |
O3—Te1—O2—Mo3 | −95.14 (8) | O12—Mo3—O10—Mo1 | 58.1 (2) |
O3i—Te1—O2—Mo3 | 84.86 (8) | O2—Mo3—O10—Mo1 | 19.96 (8) |
O1—Te1—O2—Mo1 | −84.69 (8) | O1i—Mo3—O10—Mo1 | 91.76 (10) |
O1i—Te1—O2—Mo1 | 95.31 (8) | O6—Mo3—O12—Mo2 | −70.74 (12) |
O3—Te1—O2—Mo1 | 0.92 (7) | O8—Mo3—O12—Mo2 | 179.91 (11) |
O3i—Te1—O2—Mo1 | −179.08 (7) | O10—Mo3—O12—Mo2 | 51.7 (2) |
O6—Mo3—O2—Te1 | 34.3 (3) | O2—Mo3—O12—Mo2 | 88.02 (10) |
O8—Mo3—O2—Te1 | −175.22 (9) | O1i—Mo3—O12—Mo2 | 17.12 (9) |
O12—Mo3—O2—Te1 | −75.47 (8) | O9—Mo2—O12—Mo3 | −178.97 (11) |
O10—Mo3—O2—Te1 | 87.92 (9) | O4—Mo2—O12—Mo3 | 73.50 (12) |
O1i—Mo3—O2—Te1 | 0.68 (6) | O5i—Mo2—O12—Mo3 | −52.3 (2) |
O6—Mo3—O2—Mo1 | −68.6 (2) | O1i—Mo2—O12—Mo3 | −17.17 (9) |
O8—Mo3—O2—Mo1 | 81.95 (9) | O3i—Mo2—O12—Mo3 | −88.33 (10) |
O12—Mo3—O2—Mo1 | −178.30 (7) | C2—O13—C1—C4 | 62.7 (4) |
O10—Mo3—O2—Mo1 | −14.91 (6) | C1—O13—C2—C3 | −61.4 (4) |
O1i—Mo3—O2—Mo1 | −102.15 (7) | C5—N5—C3—C2 | 140.0 (3) |
O11—Mo1—O2—Te1 | −27.3 (3) | C4—N5—C3—C2 | −49.8 (4) |
O7—Mo1—O2—Te1 | 172.66 (9) | O13—C2—C3—N5 | 54.6 (4) |
O5—Mo1—O2—Te1 | 75.44 (8) | C5—N5—C4—C1 | −137.4 (3) |
O10—Mo1—O2—Te1 | −88.10 (9) | C3—N5—C4—C1 | 52.3 (4) |
O3—Mo1—O2—Te1 | −0.83 (6) | O13—C1—C4—N5 | −58.5 (4) |
O11—Mo1—O2—Mo3 | 76.2 (3) | C3—N5—C5—N4 | 11.6 (5) |
O7—Mo1—O2—Mo3 | −83.85 (8) | C4—N5—C5—N4 | −157.6 (3) |
O5—Mo1—O2—Mo3 | 178.93 (7) | C3—N5—C5—N3 | −165.4 (3) |
O10—Mo1—O2—Mo3 | 15.38 (6) | C4—N5—C5—N3 | 25.3 (4) |
O3—Mo1—O2—Mo3 | 102.65 (7) | C6—N3—C5—N4 | 55.3 (4) |
O2—Te1—O3—Mo2i | −95.00 (8) | C6—N3—C5—N5 | −127.5 (3) |
O2i—Te1—O3—Mo2i | 85.00 (8) | C5—N3—C6—N2 | −179.4 (3) |
O1—Te1—O3—Mo2i | −0.40 (7) | C5—N3—C6—N1 | 3.6 (5) |
O1i—Te1—O3—Mo2i | 179.60 (7) | C8—O14—C7—C10 | 59.6 (4) |
O2—Te1—O3—Mo1 | −0.94 (7) | C7—O14—C8—C9 | −62.0 (4) |
O2i—Te1—O3—Mo1 | 179.06 (7) | C11—N10—C9—C8 | 148.7 (3) |
O1—Te1—O3—Mo1 | 93.67 (8) | C10—N10—C9—C8 | −47.8 (4) |
O1i—Te1—O3—Mo1 | −86.33 (8) | O14—C8—C9—N10 | 56.0 (4) |
O11—Mo1—O3—Te1 | 172.42 (9) | C11—N10—C10—C7 | −150.2 (3) |
O7—Mo1—O3—Te1 | −18.7 (3) | C9—N10—C10—C7 | 46.0 (4) |
O5—Mo1—O3—Te1 | −87.41 (9) | O14—C7—C10—N10 | −51.7 (4) |
O10—Mo1—O3—Te1 | 75.53 (8) | C10—N10—C11—N9 | −162.6 (3) |
O2—Mo1—O3—Te1 | 0.83 (6) | C9—N10—C11—N9 | −0.1 (4) |
O11—Mo1—O3—Mo2i | −85.20 (9) | C10—N10—C11—N8 | 23.3 (4) |
O7—Mo1—O3—Mo2i | 83.6 (2) | C9—N10—C11—N8 | −174.2 (3) |
O5—Mo1—O3—Mo2i | 14.98 (7) | C12—N8—C11—N10 | −154.6 (3) |
O10—Mo1—O3—Mo2i | 177.91 (7) | C12—N8—C11—N9 | 31.6 (5) |
O2—Mo1—O3—Mo2i | 103.21 (7) | C11—N8—C12—N7 | 30.2 (5) |
O11—Mo1—O5—Mo2i | 70.89 (11) | C11—N8—C12—N6 | −154.1 (3) |
O7—Mo1—O5—Mo2i | 179.14 (10) |
Symmetry code: (i) −x+2, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H6···O7 | 0.90 | 2.20 | 2.916 (3) | 137 |
N1—H5···O2 | 0.90 | 2.04 | 2.769 (3) | 138 |
N2—H8···O1ii | 0.90 | 1.95 | 2.840 (3) | 172 |
N2—H7···O1W | 0.90 | 2.01 | 2.877 (3) | 162 |
N3—H9···O10iii | 0.90 | 1.69 | 2.571 (3) | 165 |
N4—H11···O11iv | 0.90 | 2.18 | 2.965 (3) | 146 |
N4—H10···O2Wii | 0.90 | 1.86 | 2.762 (4) | 177 |
N9—H17···O14v | 0.90 | 2.18 | 3.067 (4) | 167 |
N7—H15···O9 | 0.90 | 2.14 | 2.925 (4) | 146 |
N7—H14···O7vi | 0.90 | 2.05 | 2.921 (3) | 164 |
N6—H13···O8vi | 0.90 | 2.06 | 2.806 (4) | 140 |
O1W—H1···O3i | 0.85 | 1.97 | 2.810 (3) | 172 |
O1W—H2···O12 | 0.85 | 2.61 | 3.087 (3) | 117 |
O1W—H2···O14v | 0.85 | 2.25 | 3.027 (3) | 152 |
O2W—H3···O5ii | 0.85 | 2.06 | 2.860 (3) | 156 |
O2W—H4···O1W | 0.85 | 1.98 | 2.829 (4) | 176 |
Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+2, −y+1, −z; (iii) x, y−1, z; (iv) −x+3/2, y−1/2, −z−1/2; (v) −x+3/2, y−1/2, −z+1/2; (vi) x+1/2, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | (C6H15N5O)2(C6H14N5O)2[TeMo6O24].4H2O |
Mr | 1850.21 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 15.722 (3), 9.2364 (18), 19.256 (4) |
β (°) | 94.67 (3) |
V (Å3) | 2787.0 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.93 |
Crystal size (mm) | 0.24 × 0.24 × 0.22 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.643, 0.657 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20771, 4883, 4465 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.056, 1.09 |
No. of reflections | 4883 |
No. of parameters | 377 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.63, −0.86 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H6···O7 | 0.90 | 2.20 | 2.916 (3) | 136.6 |
N1—H5···O2 | 0.90 | 2.04 | 2.769 (3) | 137.8 |
N2—H8···O1i | 0.90 | 1.95 | 2.840 (3) | 171.5 |
N2—H7···O1W | 0.90 | 2.01 | 2.877 (3) | 161.7 |
N3—H9···O10ii | 0.90 | 1.69 | 2.571 (3) | 164.6 |
N4—H11···O11iii | 0.90 | 2.18 | 2.965 (3) | 145.9 |
N4—H10···O2Wi | 0.90 | 1.86 | 2.762 (4) | 176.7 |
N9—H17···O14iv | 0.90 | 2.18 | 3.067 (4) | 166.9 |
N7—H15···O9 | 0.90 | 2.14 | 2.925 (4) | 146.1 |
N7—H14···O7v | 0.90 | 2.05 | 2.921 (3) | 163.6 |
N6—H13···O8v | 0.90 | 2.06 | 2.806 (4) | 140.0 |
O1W—H1···O3vi | 0.85 | 1.97 | 2.810 (3) | 171.6 |
O1W—H2···O12 | 0.85 | 2.61 | 3.087 (3) | 116.5 |
O1W—H2···O14iv | 0.85 | 2.25 | 3.027 (3) | 151.7 |
O2W—H3···O5i | 0.85 | 2.06 | 2.860 (3) | 156.2 |
O2W—H4···O1W | 0.85 | 1.98 | 2.829 (4) | 176.3 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y−1, z; (iii) −x+3/2, y−1/2, −z−1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) x+1/2, −y+3/2, z+1/2; (vi) −x+2, −y+2, −z. |
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N-Amidino-4-morpholincarboxamidine (ABOB) is an effective broad-spectrum antiviral medicine to influenza, chickenpox and measles. In our chemical studies (Chen et al., 2007; Li et al., 2005; Liu et al., 2004), we found it is a versatile ligand capable of interacting with different types of polyanions. As a part of our ongoing work, we have investigated the reaction of ABOB and the Anderson type [TeVIMoVI6O24]6- polyanion to give a compound formulated as (H2ABOB)2(HABOB)2[TeVIMoVI6O24].4H2O (I).
The compound consists of [TeVIMoVI6O24]6-, protonated ABOB, and lattice water molecules. The three-dimensional supramolecular structure is formed by electrostatic forces and hydrogen bonding interactions among these components (Fig. 1). The [TeVIMoVI6O24]6- anion lies on an inversion center and is close to having D3 d symmetry. It is made up of six MoO6 octahedra surrounding one TeO6 octahedron by entirely edge-shared contacts; bond lengths and angles are in accordance with those of reported examples (Drewes et al., 2004; Gao et al., 2006) The diprotonated ABOB acquires two protons with its two imine groups (N2, N4). The monoprotonated ABOB acquires two protons with two imine groups (N6, N9) as well but loses one proton on the third imine groups (N8). Electrostatic forces and hydrogen bonding interactions result in a three-dimensional supramolecular structure (Figure 2, Figure 3). The hydrogen-bond donors are the protonated imines groups and water molecules whereas the acceptors are mostly the O atoms of the Anderson type polyanion.