metal-organic compounds
Pentakis(L-prolinium) dodecatungstoborate trihydrate
aFaculty of Chemistry, Islamic Azad University-North Tehran Branch, Tehran, Iran, and bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran
*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com
The title polyoxometalate-based organic-inorganic hybrid compound, (C5H10NO2)5[BW12O40]·3H2O, consists of one α-Keggin-type [BW12O40]5− polyoxoanion, five crystallographically independent L-prolinium cations and three uncoordinated water molecules. The polyoxoanion shows characteristic features with respect to bond lengths and angles. Several N—H⋯O and O—H⋯O hydrogen bonds between the organic cations, inorganic anions and crystal water molecules lead to a three-dimensional supramolecular structure.
Related literature
For other [PX12O40]3− (X = Mo, W) polyoxometalate anions with organic counter-cations, see: Pourayoubi & Mahjoub (2007); Pourayoubi et al. (2008). For synthetic details, see: Rocchiccioli-Deltcheff et al. (1983).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809047357/wm2266sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047357/wm2266Isup2.hkl
Synthesis of K5BW12O40.nH2O: K5BW12O40.nH2O was prepared according to the literature method by Rocchiccioli-Deltcheff et al. (1983). To 100 ml of water were added successively under vigorous stirring 100 g of Na2WO4.2H2O, 5 g of boric acid (H3BO3), and 60 ml of aqueous 6M HCl. The solution (pH=6) was allowed to boil for some hours, with water re-filled from time to time. The solid paratungstate Nal0W12O41.nH2O (17 g) was filtered off; the filtrate was then acidified by aqueous 6M HCl to pH=2 and allowed to boil for another 0.5 h. Precipitation of K5BW12O40.nH2O was accomplished by adding 20 g of solid KCl. After filtration and washing with Et2O, 71 g of crude product were obtained and recrystallized in 50 ml of water at 333 K. 11B-NMR (D2O, p.p.m.):-17.45. IR (KBr, cm-1): 3420 s, 1942 s, 1603 s, 959 vs, 904 vs, 811 vs, 506 m, 376 m. UV-Vis (1.2 × 10-4 M in water, λmax): 222 nm, 256 nm.
Synthesis of H5BW12O40.yH2O: The acid was prepared by passage of an aqueous solution of K5BW12O40.nH2O through a column (50 cm×1 cm) of DOWEX-50 W-X8 (H+ enriched cationic exchange resin) and subsequent evaporation of the solution to dryness. 11B-NMR (D2O, p.p.m.): -17.54. IR (KBr, cm-1): 3095b, 1702m, 1154 s, 796 vs, 529 m, 383 m. UV-Vis (1.2 × 10-4 M in water, λmax): 223 nm, 255 nm.
Synthesis of [C5H10NO2]5[BW12O40].3H2O: A solution of L-proline (0.302 g, 2.62 mmol) in HCl (15 ml, 1 M) was added dropwise to a solution of H5BW12O40.yH2O (1.5 g) in H2O (60 ml) and stirred for 2 h. The solution was filtered and kept until colorless crystals were obtained. 11B-NMR (D2O, p.p.m.): -17.45. IR (KBr, cm-1): 2928 m, 1739 m, 1579 m, 1456 m, 1369 m, 1240 m, 960 s, 907 s, 807 vs, 499 m, 425 w, 390 w. 1H-NMR (D2O, p.p.m.): 2.17 (m), 2.52 (m), 3.50 (m), 4.47 (m). 13C-NMR (D2O, p.p.m.): 23.14, 28.01, 46.21, 59.43, 171.52. UV-Vis (1.2 × 10-4 M in water, λmax): 222 nm, 256 nm.
The hydrogen atoms of organic OH and NH2 groups were found in difference Fourier synthesis and were fixed. Water H atoms could not be located unambiguously and were excluded from the
The H(C) atom positions of the organic cation were calculated. All hydrogen atoms were refined in an isotropic approximation using a riding model with Uiso(H) equal to 1.2 Ueq(Ci), for methyl groups equal to 1.5 Ueq(Cii), where U(Ci) and U(Cii) are respectively the equivalent thermal parameters of the carbon atoms to which the corresponding H atoms are bonded. The highest peak and the deepest hole in the final Fourier map are located 0.75 Å from atom W1 and 1.38 from atom O19, respectively.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. An ORTEP-style plot of the α-Keggin-type BW12O405- polyoxoanion. Ellipsoids are given at the 30% probability level. | |
Fig. 2. A view of the five symmetrically independent organic cations and the crystal water molecules. Ellipsoids are given at the 30% probability level. |
(C5H10NO2)5[BW12O40]·3H2O | F(000) = 6232 |
Mr = 3491.76 | Dx = 3.739 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1485 reflections |
a = 12.9135 (3) Å | θ = 2–25° |
b = 21.6013 (5) Å | µ = 22.27 mm−1 |
c = 22.2343 (5) Å | T = 100 K |
V = 6202.2 (2) Å3 | Prism, colorless |
Z = 4 | 0.20 × 0.10 × 0.10 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 16473 independent reflections |
Radiation source: fine-focus sealed tube | 15774 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.078 |
ϕ and ω scans | θmax = 29.0°, θmin = 1.3° |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | h = −17→17 |
Tmin = 0.084, Tmax = 0.110 | k = −29→29 |
95451 measured reflections | l = −30→30 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.06P)2 + 1.7105P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.025 |
16473 reflections | Δρmax = 3.37 e Å−3 |
865 parameters | Δρmin = −1.04 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 7492 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.008 (10) |
(C5H10NO2)5[BW12O40]·3H2O | V = 6202.2 (2) Å3 |
Mr = 3491.76 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 12.9135 (3) Å | µ = 22.27 mm−1 |
b = 21.6013 (5) Å | T = 100 K |
c = 22.2343 (5) Å | 0.20 × 0.10 × 0.10 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 16473 independent reflections |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | 15774 reflections with I > 2σ(I) |
Tmin = 0.084, Tmax = 0.110 | Rint = 0.078 |
95451 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.088 | Δρmax = 3.37 e Å−3 |
S = 1.07 | Δρmin = −1.04 e Å−3 |
16473 reflections | Absolute structure: Flack (1983), 7492 Friedel pairs |
865 parameters | Absolute structure parameter: 0.008 (10) |
0 restraints |
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 | ||
W1 | 0.48790 (3) | 0.656796 (18) | 0.276922 (17) | 0.02402 (8) | |
W2 | 0.51869 (3) | 0.622545 (18) | 0.131253 (17) | 0.02457 (8) | |
W3 | 0.63191 (3) | 0.520433 (18) | 0.326329 (17) | 0.02592 (8) | |
W4 | 0.59752 (3) | 0.757894 (18) | 0.183500 (17) | 0.02368 (8) | |
W5 | 0.71404 (3) | 0.674877 (18) | 0.373609 (16) | 0.02460 (8) | |
W6 | 0.65206 (3) | 0.482129 (17) | 0.183055 (17) | 0.02480 (8) | |
W7 | 0.82724 (3) | 0.771149 (18) | 0.277591 (17) | 0.02396 (8) | |
W8 | 0.77701 (3) | 0.584912 (18) | 0.075721 (17) | 0.02402 (8) | |
W9 | 0.86311 (3) | 0.491233 (18) | 0.266892 (17) | 0.02491 (8) | |
W10 | 0.85105 (3) | 0.725253 (18) | 0.120431 (16) | 0.02382 (8) | |
W11 | 0.94839 (3) | 0.643680 (18) | 0.320518 (17) | 0.02371 (8) | |
W12 | 0.98281 (3) | 0.601157 (18) | 0.163090 (16) | 0.02424 (8) | |
B1 | 0.7377 (8) | 0.6289 (5) | 0.2248 (4) | 0.0200 (17) | |
O1 | 0.6302 (5) | 0.6553 (3) | 0.2105 (3) | 0.0210 (12) | |
O1S | 0.4293 (6) | 0.5931 (4) | 0.9191 (4) | 0.0352 (17) | |
H1O | 0.4195 | 0.6182 | 0.8988 | 0.042* | |
O1W | 0.4607 (8) | 0.7964 (4) | 0.3734 (4) | 0.0404 (19) | |
O2 | 0.7256 (6) | 0.5594 (3) | 0.2420 (3) | 0.0222 (12) | |
O2W | 0.2460 (6) | 0.6391 (4) | 0.4227 (4) | 0.0350 (16) | |
O2S | 0.6010 (7) | 0.6037 (4) | 0.9327 (4) | 0.0382 (18) | |
O3 | 0.7868 (5) | 0.6627 (3) | 0.2765 (3) | 0.0231 (12) | |
O3W | 0.7275 (7) | 0.8309 (4) | 0.4577 (4) | 0.0359 (16) | |
O3S | 0.7876 (6) | 0.9536 (4) | 0.3750 (4) | 0.0349 (16) | |
O4 | 0.8061 (5) | 0.6326 (3) | 0.1696 (3) | 0.0241 (13) | |
O4S | 0.6491 (6) | 0.8905 (4) | 0.3642 (4) | 0.0338 (16) | |
H4O | 0.6769 | 0.8738 | 0.3989 | 0.041* | |
O5 | 0.5257 (6) | 0.5769 (3) | 0.2986 (3) | 0.0271 (14) | |
O5S | 0.4451 (6) | 0.6644 (4) | 0.4605 (3) | 0.0342 (16) | |
O6 | 0.4292 (5) | 0.6287 (3) | 0.2023 (3) | 0.0251 (13) | |
O6S | 0.4772 (8) | 0.7641 (4) | 0.4874 (4) | 0.0391 (18) | |
H6O | 0.4961 | 0.7757 | 0.4531 | 0.047* | |
O7 | 0.4925 (6) | 0.7394 (3) | 0.2423 (3) | 0.0256 (13) | |
O7S | 0.2860 (8) | 0.7803 (4) | 0.0535 (4) | 0.0416 (19) | |
H7O | 0.2990 | 0.8017 | 0.0229 | 0.062* | |
O8 | 0.5863 (5) | 0.6868 (3) | 0.3341 (3) | 0.0236 (13) | |
O8S | 0.3474 (7) | 0.8638 (4) | 0.1020 (4) | 0.0356 (17) | |
O9 | 0.5532 (6) | 0.5404 (3) | 0.1617 (3) | 0.0267 (14) | |
O9S | 0.3117 (7) | 0.5230 (4) | 0.4169 (4) | 0.0416 (19) | |
H9O | 0.3033 | 0.5608 | 0.4324 | 0.050* | |
O10 | 0.5915 (6) | 0.4682 (3) | 0.2596 (3) | 0.0299 (15) | |
O10S | 0.4223 (7) | 0.5205 (4) | 0.4950 (4) | 0.0389 (18) | |
O11 | 0.5160 (5) | 0.7088 (3) | 0.1264 (3) | 0.0250 (13) | |
O12 | 0.6896 (6) | 0.5883 (4) | 0.3686 (3) | 0.0314 (15) | |
O13 | 0.6928 (5) | 0.7809 (3) | 0.2427 (3) | 0.0241 (13) | |
O14 | 0.7592 (6) | 0.7557 (3) | 0.3529 (3) | 0.0241 (13) | |
O15 | 0.6373 (6) | 0.6135 (3) | 0.0844 (3) | 0.0268 (14) | |
O16 | 0.7606 (6) | 0.4786 (3) | 0.3293 (3) | 0.0292 (14) | |
O17 | 0.7111 (6) | 0.7484 (3) | 0.1301 (3) | 0.0269 (14) | |
O18 | 0.8576 (6) | 0.6533 (4) | 0.3872 (3) | 0.0284 (14) | |
O19 | 0.7369 (5) | 0.5154 (3) | 0.1199 (3) | 0.0251 (13) | |
O20 | 0.7781 (6) | 0.4446 (4) | 0.2136 (3) | 0.0279 (14) | |
O21 | 0.8143 (6) | 0.6694 (3) | 0.0559 (3) | 0.0248 (13) | |
O22 | 0.9096 (6) | 0.5585 (3) | 0.3152 (3) | 0.0271 (14) | |
O23 | 0.8733 (6) | 0.7575 (4) | 0.1983 (3) | 0.0302 (15) | |
O24 | 0.9457 (5) | 0.7318 (3) | 0.3100 (3) | 0.0240 (13) | |
O25 | 0.9204 (6) | 0.5700 (3) | 0.0899 (3) | 0.0273 (14) | |
O26 | 0.9358 (6) | 0.5286 (3) | 0.2028 (3) | 0.0268 (14) | |
O27 | 0.9791 (5) | 0.6809 (3) | 0.1284 (3) | 0.0246 (13) | |
O28 | 0.9970 (6) | 0.6367 (3) | 0.2391 (3) | 0.0292 (15) | |
O29 | 0.3749 (5) | 0.6661 (4) | 0.3156 (3) | 0.0285 (14) | |
O30 | 0.4232 (5) | 0.6030 (4) | 0.0816 (3) | 0.0285 (15) | |
O31 | 0.5646 (6) | 0.4846 (4) | 0.3829 (4) | 0.0347 (16) | |
O32 | 0.5517 (6) | 0.8289 (4) | 0.1618 (3) | 0.0297 (15) | |
O33 | 0.6819 (6) | 0.6906 (3) | 0.4468 (3) | 0.0278 (14) | |
O34 | 0.6062 (6) | 0.4176 (3) | 0.1473 (3) | 0.0293 (15) | |
O35 | 0.8625 (6) | 0.8463 (3) | 0.2907 (3) | 0.0290 (14) | |
O36 | 0.7750 (6) | 0.5562 (4) | 0.0047 (3) | 0.0280 (14) | |
O37 | 0.9478 (6) | 0.4343 (3) | 0.2885 (3) | 0.0286 (14) | |
O38 | 0.8953 (6) | 0.7851 (3) | 0.0763 (3) | 0.0275 (14) | |
O39 | 1.0646 (5) | 0.6363 (4) | 0.3586 (3) | 0.0272 (14) | |
O40 | 1.1101 (5) | 0.5826 (4) | 0.1480 (3) | 0.0284 (14) | |
N1 | 0.6289 (7) | 0.4792 (4) | 0.9439 (4) | 0.0297 (17) | |
H1NB | 0.6520 | 0.4592 | 0.9099 | 0.036* | |
H1NA | 0.6732 | 0.5116 | 0.9517 | 0.036* | |
N2 | 0.7218 (7) | 1.0352 (4) | 0.2922 (4) | 0.0272 (16) | |
H2NB | 0.7719 | 1.0375 | 0.3215 | 0.033* | |
H2NA | 0.6776 | 1.0682 | 0.2966 | 0.033* | |
N3 | 0.4500 (8) | 0.6235 (4) | 0.5739 (4) | 0.0320 (18) | |
H3NB | 0.3905 | 0.6209 | 0.5965 | 0.038* | |
H3NA | 0.4383 | 0.6041 | 0.5377 | 0.038* | |
N4 | 0.3201 (8) | 0.8133 (5) | 0.2120 (4) | 0.035 (2) | |
H4NB | 0.3851 | 0.8006 | 0.2236 | 0.041* | |
H4NA | 0.3224 | 0.8549 | 0.2034 | 0.041* | |
N5 | 0.4818 (7) | 0.4030 (4) | 0.4701 (4) | 0.0284 (17) | |
H5NB | 0.4970 | 0.4261 | 0.5036 | 0.034* | |
H5NA | 0.5381 | 0.4035 | 0.4447 | 0.034* | |
C1 | 0.5225 (10) | 0.5737 (5) | 0.9283 (5) | 0.033 (2) | |
C2 | 0.5198 (8) | 0.5038 (5) | 0.9335 (4) | 0.0283 (19) | |
H2A | 0.4914 | 0.4858 | 0.8954 | 0.034* | |
C3 | 0.4581 (9) | 0.4787 (5) | 0.9872 (5) | 0.033 (2) | |
H3A | 0.3853 | 0.4703 | 0.9757 | 0.040* | |
H3B | 0.4589 | 0.5084 | 1.0211 | 0.040* | |
C4 | 0.5143 (9) | 0.4184 (5) | 1.0041 (5) | 0.030 (2) | |
H4A | 0.4996 | 0.4065 | 1.0462 | 0.036* | |
H4B | 0.4941 | 0.3841 | 0.9771 | 0.036* | |
C5 | 0.6279 (9) | 0.4355 (5) | 0.9958 (5) | 0.032 (2) | |
H5A | 0.6556 | 0.4556 | 1.0325 | 0.038* | |
H5B | 0.6699 | 0.3983 | 0.9870 | 0.038* | |
C6 | 0.7076 (9) | 0.9376 (5) | 0.3491 (5) | 0.031 (2) | |
C7 | 0.6617 (8) | 0.9738 (5) | 0.2975 (5) | 0.0289 (19) | |
H7A | 0.5862 | 0.9815 | 0.3039 | 0.035* | |
C8 | 0.6816 (10) | 0.9420 (5) | 0.2356 (5) | 0.035 (2) | |
H8A | 0.6867 | 0.8966 | 0.2403 | 0.042* | |
H8B | 0.6251 | 0.9515 | 0.2070 | 0.042* | |
C9 | 0.7846 (9) | 0.9690 (5) | 0.2134 (5) | 0.031 (2) | |
H9A | 0.8443 | 0.9503 | 0.2346 | 0.037* | |
H9B | 0.7931 | 0.9632 | 0.1695 | 0.037* | |
C10 | 0.7721 (9) | 1.0363 (5) | 0.2293 (5) | 0.031 (2) | |
H10A | 0.7269 | 1.0577 | 0.1999 | 0.037* | |
H10B | 0.8401 | 1.0575 | 0.2305 | 0.037* | |
C11 | 0.4650 (8) | 0.7049 (5) | 0.4984 (5) | 0.030 (2) | |
C12 | 0.4773 (9) | 0.6902 (5) | 0.5634 (4) | 0.0281 (19) | |
H12A | 0.4310 | 0.7175 | 0.5879 | 0.034* | |
C13 | 0.5897 (9) | 0.6957 (5) | 0.5863 (4) | 0.031 (2) | |
H13A | 0.5915 | 0.7129 | 0.6275 | 0.037* | |
H13B | 0.6312 | 0.7227 | 0.5595 | 0.037* | |
C14 | 0.6314 (10) | 0.6283 (6) | 0.5852 (5) | 0.037 (2) | |
H14A | 0.6529 | 0.6158 | 0.5443 | 0.045* | |
H14B | 0.6902 | 0.6229 | 0.6133 | 0.045* | |
C15 | 0.5367 (9) | 0.5927 (6) | 0.6060 (5) | 0.036 (2) | |
H15A | 0.5417 | 0.5485 | 0.5946 | 0.043* | |
H15B | 0.5279 | 0.5958 | 0.6501 | 0.043* | |
C16 | 0.3092 (9) | 0.8113 (5) | 0.1013 (5) | 0.035 (2) | |
C17 | 0.2839 (9) | 0.7769 (6) | 0.1577 (5) | 0.034 (2) | |
H17A | 0.3215 | 0.7364 | 0.1569 | 0.041* | |
C18 | 0.1722 (11) | 0.7646 (9) | 0.1700 (7) | 0.057 (4) | |
H18A | 0.1477 | 0.7275 | 0.1481 | 0.068* | |
H18B | 0.1288 | 0.8005 | 0.1587 | 0.068* | |
C19 | 0.1709 (14) | 0.7542 (11) | 0.2365 (7) | 0.071 (6) | |
H19A | 0.1002 | 0.7602 | 0.2528 | 0.085* | |
H19B | 0.1945 | 0.7118 | 0.2463 | 0.085* | |
C20 | 0.2427 (10) | 0.8008 (5) | 0.2611 (6) | 0.037 (2) | |
H20A | 0.2777 | 0.7847 | 0.2975 | 0.044* | |
H20B | 0.2050 | 0.8392 | 0.2719 | 0.044* | |
C21 | 0.3792 (9) | 0.4961 (5) | 0.4548 (5) | 0.032 (2) | |
C22 | 0.3904 (11) | 0.4276 (5) | 0.4397 (7) | 0.044 (3) | |
H22A | 0.3974 | 0.4221 | 0.3952 | 0.053* | |
C23 | 0.2989 (12) | 0.3902 (8) | 0.4629 (12) | 0.075 (6) | |
H23A | 0.2485 | 0.4177 | 0.4832 | 0.090* | |
H23B | 0.2635 | 0.3690 | 0.4292 | 0.090* | |
C24 | 0.3413 (10) | 0.3438 (7) | 0.5063 (6) | 0.045 (3) | |
H24A | 0.3041 | 0.3039 | 0.5029 | 0.054* | |
H24B | 0.3356 | 0.3591 | 0.5482 | 0.054* | |
C25 | 0.4547 (9) | 0.3368 (5) | 0.4877 (5) | 0.034 (2) | |
H25A | 0.4980 | 0.3222 | 0.5216 | 0.041* | |
H25B | 0.4623 | 0.3081 | 0.4533 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
W1 | 0.02403 (17) | 0.02409 (17) | 0.02394 (16) | −0.00038 (13) | 0.00101 (14) | −0.00086 (13) |
W2 | 0.02475 (17) | 0.02495 (17) | 0.02402 (16) | −0.00076 (14) | −0.00093 (14) | −0.00166 (13) |
W3 | 0.02953 (19) | 0.02317 (17) | 0.02507 (16) | 0.00055 (14) | 0.00420 (14) | 0.00201 (13) |
W4 | 0.02451 (17) | 0.02244 (17) | 0.02408 (16) | 0.00017 (13) | −0.00103 (14) | 0.00037 (13) |
W5 | 0.02514 (17) | 0.02672 (18) | 0.02194 (15) | 0.00076 (14) | 0.00060 (14) | −0.00149 (13) |
W6 | 0.02673 (18) | 0.02187 (17) | 0.02580 (16) | −0.00172 (14) | 0.00042 (14) | −0.00100 (13) |
W7 | 0.02653 (18) | 0.02181 (16) | 0.02353 (15) | −0.00008 (13) | −0.00197 (14) | −0.00132 (13) |
W8 | 0.02555 (18) | 0.02436 (17) | 0.02216 (15) | −0.00149 (14) | 0.00052 (14) | −0.00160 (13) |
W9 | 0.02780 (18) | 0.02266 (16) | 0.02428 (16) | 0.00153 (14) | 0.00033 (14) | 0.00044 (13) |
W10 | 0.02612 (17) | 0.02229 (16) | 0.02304 (15) | −0.00099 (14) | 0.00081 (14) | 0.00083 (13) |
W11 | 0.02437 (17) | 0.02433 (17) | 0.02243 (15) | 0.00041 (13) | −0.00105 (13) | 0.00032 (13) |
W12 | 0.02416 (17) | 0.02574 (18) | 0.02283 (15) | 0.00163 (14) | 0.00070 (14) | 0.00029 (13) |
B1 | 0.026 (5) | 0.018 (4) | 0.016 (4) | −0.001 (3) | 0.006 (3) | −0.001 (3) |
O1 | 0.023 (3) | 0.019 (3) | 0.021 (3) | 0.000 (2) | 0.007 (2) | −0.002 (2) |
O1S | 0.036 (4) | 0.030 (4) | 0.039 (4) | 0.004 (3) | −0.003 (3) | 0.006 (3) |
O1W | 0.056 (5) | 0.029 (4) | 0.037 (4) | 0.004 (4) | 0.005 (4) | 0.004 (3) |
O2 | 0.029 (3) | 0.015 (3) | 0.023 (3) | 0.001 (2) | 0.005 (3) | 0.000 (2) |
O2W | 0.028 (4) | 0.044 (4) | 0.033 (4) | −0.001 (3) | −0.003 (3) | −0.004 (3) |
O2S | 0.036 (4) | 0.034 (4) | 0.045 (4) | −0.004 (3) | −0.003 (4) | 0.001 (3) |
O3 | 0.024 (3) | 0.025 (3) | 0.020 (3) | 0.001 (3) | 0.000 (2) | −0.002 (2) |
O3W | 0.040 (4) | 0.037 (4) | 0.031 (3) | −0.001 (3) | 0.002 (3) | −0.002 (3) |
O3S | 0.032 (4) | 0.030 (4) | 0.043 (4) | −0.003 (3) | −0.001 (3) | −0.002 (3) |
O4 | 0.027 (3) | 0.022 (3) | 0.023 (3) | 0.000 (2) | 0.000 (3) | −0.002 (2) |
O4S | 0.033 (4) | 0.032 (4) | 0.037 (4) | 0.001 (3) | 0.006 (3) | 0.004 (3) |
O5 | 0.026 (3) | 0.027 (3) | 0.028 (3) | 0.001 (3) | 0.001 (3) | −0.001 (3) |
O5S | 0.034 (4) | 0.041 (4) | 0.027 (3) | −0.007 (3) | 0.001 (3) | −0.001 (3) |
O6 | 0.021 (3) | 0.032 (4) | 0.023 (3) | 0.000 (3) | −0.006 (2) | −0.003 (3) |
O6S | 0.056 (5) | 0.030 (4) | 0.032 (4) | 0.002 (4) | −0.001 (4) | 0.006 (3) |
O7 | 0.026 (3) | 0.023 (3) | 0.028 (3) | 0.001 (3) | 0.000 (3) | 0.003 (2) |
O7S | 0.055 (5) | 0.040 (4) | 0.030 (4) | −0.010 (4) | −0.003 (4) | 0.005 (3) |
O8 | 0.022 (3) | 0.028 (3) | 0.021 (3) | 0.004 (2) | −0.002 (2) | 0.003 (2) |
O8S | 0.036 (4) | 0.033 (4) | 0.038 (4) | −0.007 (3) | 0.000 (3) | 0.002 (3) |
O9 | 0.030 (3) | 0.021 (3) | 0.028 (3) | −0.002 (3) | −0.003 (3) | −0.004 (3) |
O9S | 0.047 (5) | 0.032 (4) | 0.046 (4) | 0.006 (4) | −0.008 (4) | 0.000 (4) |
O10 | 0.033 (4) | 0.026 (3) | 0.031 (3) | −0.006 (3) | 0.010 (3) | 0.000 (3) |
O10S | 0.051 (5) | 0.032 (4) | 0.034 (4) | 0.004 (4) | −0.008 (4) | −0.005 (3) |
O11 | 0.026 (3) | 0.022 (3) | 0.027 (3) | 0.003 (3) | −0.002 (3) | −0.003 (2) |
O12 | 0.031 (4) | 0.031 (4) | 0.032 (3) | 0.002 (3) | 0.002 (3) | 0.000 (3) |
O13 | 0.022 (3) | 0.022 (3) | 0.028 (3) | −0.001 (2) | −0.001 (3) | −0.003 (2) |
O14 | 0.028 (3) | 0.019 (3) | 0.024 (3) | 0.000 (3) | 0.002 (3) | −0.004 (2) |
O15 | 0.032 (4) | 0.024 (3) | 0.024 (3) | 0.001 (3) | 0.004 (3) | −0.004 (2) |
O16 | 0.033 (4) | 0.028 (3) | 0.027 (3) | 0.001 (3) | −0.002 (3) | 0.003 (3) |
O17 | 0.025 (3) | 0.032 (4) | 0.023 (3) | 0.002 (3) | 0.008 (3) | 0.000 (3) |
O18 | 0.027 (3) | 0.031 (4) | 0.027 (3) | 0.002 (3) | −0.005 (3) | 0.001 (3) |
O19 | 0.017 (3) | 0.032 (3) | 0.026 (3) | −0.001 (3) | 0.002 (2) | 0.002 (3) |
O20 | 0.027 (3) | 0.032 (4) | 0.025 (3) | 0.001 (3) | 0.004 (3) | 0.001 (3) |
O21 | 0.031 (4) | 0.020 (3) | 0.023 (3) | 0.002 (3) | −0.002 (3) | −0.002 (2) |
O22 | 0.034 (4) | 0.020 (3) | 0.027 (3) | 0.006 (3) | −0.002 (3) | 0.002 (3) |
O23 | 0.038 (4) | 0.030 (4) | 0.023 (3) | −0.002 (3) | 0.000 (3) | 0.001 (3) |
O24 | 0.025 (3) | 0.028 (3) | 0.020 (3) | 0.000 (3) | −0.001 (2) | −0.001 (2) |
O25 | 0.028 (3) | 0.029 (4) | 0.025 (3) | 0.007 (3) | −0.004 (3) | −0.004 (3) |
O26 | 0.024 (3) | 0.027 (3) | 0.030 (3) | −0.002 (3) | 0.009 (3) | −0.001 (3) |
O27 | 0.022 (3) | 0.025 (3) | 0.026 (3) | 0.002 (3) | −0.001 (3) | 0.001 (2) |
O28 | 0.041 (4) | 0.025 (3) | 0.022 (3) | −0.006 (3) | 0.003 (3) | −0.007 (2) |
O29 | 0.023 (3) | 0.036 (4) | 0.027 (3) | 0.000 (3) | 0.011 (3) | 0.001 (3) |
O30 | 0.021 (3) | 0.031 (4) | 0.033 (3) | −0.003 (3) | −0.009 (3) | −0.013 (3) |
O31 | 0.037 (4) | 0.034 (4) | 0.034 (4) | −0.001 (3) | 0.012 (3) | 0.005 (3) |
O32 | 0.030 (4) | 0.034 (4) | 0.025 (3) | 0.009 (3) | −0.001 (3) | 0.000 (3) |
O33 | 0.033 (4) | 0.026 (3) | 0.024 (3) | −0.001 (3) | 0.003 (3) | −0.005 (3) |
O34 | 0.033 (4) | 0.018 (3) | 0.037 (4) | −0.009 (3) | 0.000 (3) | −0.011 (3) |
O35 | 0.034 (4) | 0.023 (3) | 0.030 (3) | −0.002 (3) | 0.000 (3) | −0.001 (3) |
O36 | 0.030 (4) | 0.031 (4) | 0.023 (3) | −0.001 (3) | 0.001 (3) | −0.004 (3) |
O37 | 0.032 (4) | 0.027 (3) | 0.026 (3) | 0.008 (3) | −0.005 (3) | 0.003 (3) |
O38 | 0.035 (4) | 0.018 (3) | 0.029 (3) | −0.004 (3) | 0.006 (3) | 0.010 (3) |
O39 | 0.018 (3) | 0.037 (4) | 0.026 (3) | 0.004 (3) | −0.006 (3) | 0.000 (3) |
O40 | 0.019 (3) | 0.035 (4) | 0.031 (3) | 0.004 (3) | 0.005 (3) | 0.001 (3) |
N1 | 0.031 (4) | 0.032 (4) | 0.027 (4) | 0.000 (3) | −0.001 (3) | −0.006 (3) |
N2 | 0.024 (4) | 0.026 (4) | 0.031 (4) | 0.000 (3) | −0.001 (3) | 0.003 (3) |
N3 | 0.033 (5) | 0.032 (5) | 0.030 (4) | 0.002 (4) | 0.004 (4) | −0.002 (3) |
N4 | 0.032 (5) | 0.043 (5) | 0.028 (4) | −0.005 (4) | −0.004 (4) | 0.001 (4) |
N5 | 0.027 (4) | 0.036 (5) | 0.022 (3) | 0.000 (4) | −0.001 (3) | 0.001 (3) |
C1 | 0.042 (6) | 0.031 (5) | 0.025 (4) | 0.006 (4) | −0.001 (4) | −0.002 (4) |
C2 | 0.029 (5) | 0.029 (5) | 0.027 (4) | 0.000 (4) | 0.000 (4) | 0.000 (4) |
C3 | 0.041 (6) | 0.022 (5) | 0.038 (5) | 0.005 (4) | 0.012 (5) | −0.002 (4) |
C4 | 0.037 (5) | 0.022 (4) | 0.032 (5) | 0.006 (4) | 0.000 (4) | 0.004 (4) |
C5 | 0.036 (5) | 0.032 (5) | 0.027 (4) | −0.002 (4) | −0.004 (4) | 0.000 (4) |
C6 | 0.030 (5) | 0.031 (5) | 0.032 (5) | 0.001 (4) | 0.008 (4) | −0.006 (4) |
C7 | 0.028 (5) | 0.023 (4) | 0.036 (5) | −0.004 (4) | −0.004 (4) | −0.006 (4) |
C8 | 0.050 (7) | 0.024 (5) | 0.032 (5) | 0.005 (4) | −0.006 (5) | −0.012 (4) |
C9 | 0.033 (5) | 0.031 (5) | 0.030 (4) | 0.006 (4) | −0.003 (4) | 0.002 (4) |
C10 | 0.033 (5) | 0.030 (5) | 0.029 (4) | −0.002 (4) | 0.003 (4) | 0.000 (4) |
C11 | 0.020 (4) | 0.041 (6) | 0.029 (4) | −0.001 (4) | −0.001 (4) | 0.002 (4) |
C12 | 0.036 (5) | 0.024 (4) | 0.025 (4) | 0.004 (4) | 0.004 (4) | −0.004 (3) |
C13 | 0.032 (5) | 0.041 (6) | 0.021 (4) | −0.001 (4) | −0.001 (4) | −0.001 (4) |
C14 | 0.038 (6) | 0.044 (6) | 0.029 (5) | 0.007 (5) | 0.006 (4) | 0.000 (4) |
C15 | 0.041 (6) | 0.035 (6) | 0.030 (5) | 0.009 (5) | 0.004 (4) | 0.002 (4) |
C16 | 0.035 (5) | 0.029 (5) | 0.041 (5) | 0.005 (4) | 0.000 (5) | 0.005 (4) |
C17 | 0.030 (5) | 0.045 (6) | 0.028 (4) | −0.004 (5) | 0.000 (4) | 0.002 (4) |
C18 | 0.038 (7) | 0.088 (12) | 0.044 (7) | −0.020 (7) | −0.005 (6) | −0.001 (7) |
C19 | 0.055 (9) | 0.109 (15) | 0.047 (8) | −0.042 (10) | 0.005 (7) | 0.003 (9) |
C20 | 0.042 (6) | 0.027 (5) | 0.042 (6) | −0.002 (4) | 0.017 (5) | 0.003 (4) |
C21 | 0.033 (5) | 0.031 (5) | 0.031 (5) | −0.001 (4) | 0.004 (4) | 0.000 (4) |
C22 | 0.052 (7) | 0.024 (5) | 0.057 (7) | −0.003 (5) | −0.021 (6) | 0.006 (5) |
C23 | 0.035 (7) | 0.044 (8) | 0.148 (19) | −0.004 (6) | −0.005 (10) | 0.016 (10) |
C24 | 0.035 (6) | 0.060 (8) | 0.041 (6) | −0.012 (6) | −0.004 (5) | 0.010 (6) |
C25 | 0.041 (6) | 0.029 (5) | 0.031 (5) | −0.004 (4) | −0.004 (4) | 0.004 (4) |
W1—O29 | 1.706 (7) | O6S—C11 | 1.312 (14) |
W1—O5 | 1.857 (7) | O6S—H6O | 0.8390 |
W1—O8 | 1.911 (7) | O7S—C16 | 1.292 (15) |
W1—O6 | 1.924 (6) | O7S—H7O | 0.8400 |
W1—O7 | 1.945 (7) | O8S—C16 | 1.235 (14) |
W1—O1 | 2.357 (6) | O9S—C21 | 1.344 (14) |
W2—O30 | 1.708 (6) | O9S—H9O | 0.8951 |
W2—O15 | 1.863 (7) | O10S—C21 | 1.178 (14) |
W2—O11 | 1.866 (7) | N1—C5 | 1.493 (14) |
W2—O9 | 1.951 (7) | N1—C2 | 1.524 (14) |
W2—O6 | 1.961 (7) | N1—H1NB | 0.9200 |
W2—O1 | 2.384 (7) | N1—H1NA | 0.9200 |
W3—O31 | 1.713 (7) | N2—C7 | 1.540 (13) |
W3—O16 | 1.892 (8) | N2—C10 | 1.541 (13) |
W3—O12 | 1.894 (8) | N2—H2NB | 0.9200 |
W3—O10 | 1.935 (8) | N2—H2NA | 0.9200 |
W3—O5 | 1.937 (7) | N3—C15 | 1.485 (15) |
W3—O2 | 2.385 (6) | N3—C12 | 1.502 (14) |
W4—O32 | 1.713 (7) | N3—H3NB | 0.9200 |
W4—O13 | 1.869 (7) | N3—H3NA | 0.9200 |
W4—O17 | 1.898 (7) | N4—C20 | 1.504 (14) |
W4—O7 | 1.926 (7) | N4—C17 | 1.516 (14) |
W4—O11 | 1.961 (7) | N4—H4NB | 0.9200 |
W4—O1 | 2.334 (6) | N4—H4NA | 0.9200 |
W5—O33 | 1.713 (7) | N5—C22 | 1.460 (15) |
W5—O8 | 1.886 (7) | N5—C25 | 1.522 (14) |
W5—O14 | 1.897 (7) | N5—H5NB | 0.9200 |
W5—O12 | 1.900 (8) | N5—H5NA | 0.9200 |
W5—O18 | 1.935 (7) | C1—C2 | 1.516 (15) |
W5—O3 | 2.369 (6) | C2—C3 | 1.534 (14) |
W6—O34 | 1.711 (6) | C2—H2A | 1.0000 |
W6—O9 | 1.854 (7) | C3—C4 | 1.537 (14) |
W6—O10 | 1.898 (7) | C3—H3A | 0.9900 |
W6—O19 | 1.921 (7) | C3—H3B | 0.9900 |
W6—O20 | 1.942 (8) | C4—C5 | 1.523 (16) |
W6—O2 | 2.325 (7) | C4—H4A | 0.9900 |
W7—O35 | 1.711 (7) | C4—H4B | 0.9900 |
W7—O23 | 1.883 (7) | C5—H5A | 0.9900 |
W7—O24 | 1.892 (7) | C5—H5B | 0.9900 |
W7—O13 | 1.913 (7) | C6—C7 | 1.511 (16) |
W7—O14 | 1.920 (7) | C7—C8 | 1.559 (14) |
W7—O3 | 2.400 (7) | C7—H7A | 1.0000 |
W8—O36 | 1.697 (7) | C8—C9 | 1.533 (17) |
W8—O19 | 1.868 (7) | C8—H8A | 0.9900 |
W8—O25 | 1.906 (7) | C8—H8B | 0.9900 |
W8—O15 | 1.916 (8) | C9—C10 | 1.505 (15) |
W8—O21 | 1.939 (7) | C9—H9A | 0.9900 |
W8—O4 | 2.359 (6) | C9—H9B | 0.9900 |
W9—O37 | 1.715 (7) | C10—H10A | 0.9900 |
W9—O26 | 1.887 (7) | C10—H10B | 0.9900 |
W9—O20 | 1.903 (8) | C11—C12 | 1.487 (14) |
W9—O22 | 1.904 (7) | C12—C13 | 1.542 (15) |
W9—O16 | 1.937 (7) | C12—H12A | 1.0000 |
W9—O2 | 2.373 (7) | C13—C14 | 1.552 (17) |
W10—O38 | 1.721 (6) | C13—H13A | 0.9900 |
W10—O17 | 1.887 (7) | C13—H13B | 0.9900 |
W10—O23 | 1.889 (7) | C14—C15 | 1.516 (18) |
W10—O27 | 1.920 (7) | C14—H14A | 0.9900 |
W10—O21 | 1.934 (7) | C14—H14B | 0.9900 |
W10—O4 | 2.354 (7) | C15—H15A | 0.9900 |
W11—O39 | 1.730 (7) | C15—H15B | 0.9900 |
W11—O18 | 1.901 (7) | C16—C17 | 1.494 (15) |
W11—O22 | 1.911 (7) | C17—C18 | 1.492 (17) |
W11—O24 | 1.919 (7) | C17—H17A | 1.0000 |
W11—O28 | 1.921 (7) | C18—C19 | 1.49 (2) |
W11—O3 | 2.341 (7) | C18—H18A | 0.9900 |
W12—O40 | 1.725 (7) | C18—H18B | 0.9900 |
W12—O28 | 1.866 (6) | C19—C20 | 1.47 (2) |
W12—O27 | 1.888 (7) | C19—H19A | 0.9900 |
W12—O26 | 1.900 (7) | C19—H19B | 0.9900 |
W12—O25 | 1.936 (7) | C20—H20A | 0.9900 |
W12—O4 | 2.385 (7) | C20—H20B | 0.9900 |
B1—O3 | 1.503 (12) | C21—C22 | 1.525 (17) |
B1—O4 | 1.513 (12) | C22—C23 | 1.52 (2) |
B1—O1 | 1.534 (13) | C22—H22A | 1.0000 |
B1—O2 | 1.556 (12) | C23—C24 | 1.49 (2) |
O1S—C1 | 1.291 (14) | C23—H23A | 0.9900 |
O1S—H1O | 0.7151 | C23—H23B | 0.9900 |
O2S—C1 | 1.206 (15) | C24—C25 | 1.529 (18) |
O3S—C6 | 1.232 (14) | C24—H24A | 0.9900 |
O4S—C6 | 1.310 (14) | C24—H24B | 0.9900 |
O4S—H4O | 0.9251 | C25—H25A | 0.9900 |
O5S—C11 | 1.243 (14) | C25—H25B | 0.9900 |
O29—W1—O5 | 101.7 (3) | B1—O3—W7 | 125.0 (5) |
O29—W1—O8 | 101.2 (3) | W11—O3—W7 | 88.5 (2) |
O5—W1—O8 | 88.1 (3) | W5—O3—W7 | 88.2 (2) |
O29—W1—O6 | 97.7 (3) | B1—O4—W10 | 124.4 (5) |
O5—W1—O6 | 92.0 (3) | B1—O4—W8 | 126.9 (6) |
O8—W1—O6 | 160.7 (3) | W10—O4—W8 | 89.9 (2) |
O29—W1—O7 | 96.7 (3) | B1—O4—W12 | 126.4 (6) |
O5—W1—O7 | 161.4 (3) | W10—O4—W12 | 88.7 (2) |
O8—W1—O7 | 86.1 (3) | W8—O4—W12 | 88.5 (2) |
O6—W1—O7 | 87.7 (3) | C6—O4S—H4O | 107.0 |
O29—W1—O1 | 169.8 (3) | W1—O5—W3 | 148.7 (4) |
O5—W1—O1 | 86.9 (3) | W1—O6—W2 | 118.9 (3) |
O8—W1—O1 | 84.4 (3) | C11—O6S—H6O | 119.8 |
O6—W1—O1 | 76.3 (3) | W4—O7—W1 | 118.7 (4) |
O7—W1—O1 | 75.0 (3) | C16—O7S—H7O | 109.5 |
O30—W2—O15 | 101.9 (3) | W5—O8—W1 | 147.7 (4) |
O30—W2—O11 | 101.3 (3) | W6—O9—W2 | 149.7 (4) |
O15—W2—O11 | 95.0 (3) | C21—O9S—H9O | 103.3 |
O30—W2—O9 | 99.5 (3) | W6—O10—W3 | 118.9 (4) |
O15—W2—O9 | 84.9 (3) | W2—O11—W4 | 119.5 (3) |
O11—W2—O9 | 158.8 (3) | W3—O12—W5 | 148.9 (4) |
O30—W2—O6 | 96.4 (3) | W4—O13—W7 | 148.6 (4) |
O15—W2—O6 | 160.4 (3) | W5—O14—W7 | 120.8 (3) |
O11—W2—O6 | 88.2 (3) | W2—O15—W8 | 149.8 (4) |
O9—W2—O6 | 85.2 (3) | W3—O16—W9 | 120.5 (4) |
O30—W2—O1 | 170.9 (3) | W10—O17—W4 | 147.1 (4) |
O15—W2—O1 | 87.0 (3) | W11—O18—W5 | 119.7 (4) |
O11—W2—O1 | 76.0 (3) | W8—O19—W6 | 147.5 (4) |
O9—W2—O1 | 82.9 (3) | W9—O20—W6 | 118.7 (4) |
O6—W2—O1 | 75.0 (2) | W10—O21—W8 | 118.6 (3) |
O31—W3—O16 | 101.8 (4) | W9—O22—W11 | 148.5 (4) |
O31—W3—O12 | 100.7 (4) | W7—O23—W10 | 150.2 (5) |
O16—W3—O12 | 90.4 (3) | W7—O24—W11 | 120.4 (4) |
O31—W3—O10 | 99.3 (3) | W8—O25—W12 | 119.0 (4) |
O16—W3—O10 | 89.1 (3) | W9—O26—W12 | 149.6 (4) |
O12—W3—O10 | 159.7 (3) | W12—O27—W10 | 121.0 (4) |
O31—W3—O5 | 99.1 (4) | W12—O28—W11 | 148.6 (4) |
O16—W3—O5 | 159.1 (3) | C5—N1—C2 | 109.2 (8) |
O12—W3—O5 | 87.1 (3) | C5—N1—H1NB | 109.8 |
O10—W3—O5 | 86.2 (3) | C2—N1—H1NB | 109.8 |
O31—W3—O2 | 173.6 (3) | C5—N1—H1NA | 109.8 |
O16—W3—O2 | 75.6 (3) | C2—N1—H1NA | 109.8 |
O12—W3—O2 | 85.3 (3) | H1NB—N1—H1NA | 108.3 |
O10—W3—O2 | 74.9 (3) | C7—N2—C10 | 107.2 (8) |
O5—W3—O2 | 83.5 (3) | C7—N2—H2NB | 110.3 |
O32—W4—O13 | 100.8 (3) | C10—N2—H2NB | 110.3 |
O32—W4—O17 | 100.8 (3) | C7—N2—H2NA | 110.3 |
O13—W4—O17 | 87.7 (3) | C10—N2—H2NA | 110.3 |
O32—W4—O7 | 97.6 (3) | H2NB—N2—H2NA | 108.5 |
O13—W4—O7 | 92.3 (3) | C15—N3—C12 | 109.1 (9) |
O17—W4—O7 | 161.2 (3) | C15—N3—H3NB | 109.9 |
O32—W4—O11 | 96.7 (3) | C12—N3—H3NB | 109.9 |
O13—W4—O11 | 162.4 (3) | C15—N3—H3NA | 109.9 |
O17—W4—O11 | 87.2 (3) | C12—N3—H3NA | 109.9 |
O7—W4—O11 | 87.1 (3) | H3NB—N3—H3NA | 108.3 |
O32—W4—O1 | 170.0 (3) | C20—N4—C17 | 106.4 (9) |
O13—W4—O1 | 87.3 (3) | C20—N4—H4NB | 110.5 |
O17—W4—O1 | 85.3 (3) | C17—N4—H4NB | 110.5 |
O7—W4—O1 | 75.9 (3) | C20—N4—H4NA | 110.5 |
O11—W4—O1 | 75.5 (3) | C17—N4—H4NA | 110.5 |
O33—W5—O8 | 101.7 (3) | H4NB—N4—H4NA | 108.6 |
O33—W5—O14 | 97.0 (3) | C22—N5—C25 | 106.0 (9) |
O8—W5—O14 | 91.7 (3) | C22—N5—H5NB | 110.5 |
O33—W5—O12 | 102.2 (3) | C25—N5—H5NB | 110.5 |
O8—W5—O12 | 87.8 (3) | C22—N5—H5NA | 110.5 |
O14—W5—O12 | 160.5 (3) | C25—N5—H5NA | 110.5 |
O33—W5—O18 | 97.6 (3) | H5NB—N5—H5NA | 108.7 |
O8—W5—O18 | 160.6 (3) | O2S—C1—O1S | 128.5 (11) |
O14—W5—O18 | 88.0 (3) | O2S—C1—C2 | 123.2 (11) |
O12—W5—O18 | 86.1 (3) | O1S—C1—C2 | 108.2 (10) |
O33—W5—O3 | 169.6 (3) | C1—C2—N1 | 109.7 (9) |
O8—W5—O3 | 86.4 (3) | C1—C2—C3 | 115.1 (9) |
O14—W5—O3 | 76.1 (3) | N1—C2—C3 | 103.9 (8) |
O12—W5—O3 | 84.4 (3) | C1—C2—H2A | 109.3 |
O18—W5—O3 | 74.7 (3) | N1—C2—H2A | 109.3 |
O34—W6—O9 | 101.3 (3) | C3—C2—H2A | 109.3 |
O34—W6—O10 | 98.3 (3) | C2—C3—C4 | 104.2 (8) |
O9—W6—O10 | 93.1 (3) | C2—C3—H3A | 110.9 |
O34—W6—O19 | 99.3 (3) | C4—C3—H3A | 110.9 |
O9—W6—O19 | 87.2 (3) | C2—C3—H3B | 110.9 |
O10—W6—O19 | 161.9 (3) | C4—C3—H3B | 110.9 |
O34—W6—O20 | 96.5 (4) | H3A—C3—H3B | 108.9 |
O9—W6—O20 | 161.9 (3) | C5—C4—C3 | 102.8 (9) |
O10—W6—O20 | 88.0 (3) | C5—C4—H4A | 111.2 |
O19—W6—O20 | 86.2 (3) | C3—C4—H4A | 111.2 |
O34—W6—O2 | 171.3 (3) | C5—C4—H4B | 111.2 |
O9—W6—O2 | 86.5 (3) | C3—C4—H4B | 111.2 |
O10—W6—O2 | 77.1 (3) | H4A—C4—H4B | 109.1 |
O19—W6—O2 | 84.9 (3) | N1—C5—C4 | 104.8 (9) |
O20—W6—O2 | 76.1 (3) | N1—C5—H5A | 110.8 |
O35—W7—O23 | 102.9 (3) | C4—C5—H5A | 110.8 |
O35—W7—O24 | 98.4 (3) | N1—C5—H5B | 110.8 |
O23—W7—O24 | 91.8 (3) | C4—C5—H5B | 110.8 |
O35—W7—O13 | 101.9 (3) | H5A—C5—H5B | 108.9 |
O23—W7—O13 | 85.6 (3) | O3S—C6—O4S | 125.6 (11) |
O24—W7—O13 | 159.6 (3) | O3S—C6—C7 | 122.6 (10) |
O35—W7—O14 | 98.0 (3) | O4S—C6—C7 | 111.7 (9) |
O23—W7—O14 | 159.0 (3) | C6—C7—N2 | 107.9 (8) |
O24—W7—O14 | 87.7 (3) | C6—C7—C8 | 112.2 (9) |
O13—W7—O14 | 87.6 (3) | N2—C7—C8 | 103.2 (9) |
O35—W7—O3 | 170.3 (3) | C6—C7—H7A | 111.1 |
O23—W7—O3 | 84.7 (3) | N2—C7—H7A | 111.1 |
O24—W7—O3 | 75.0 (3) | C8—C7—H7A | 111.1 |
O13—W7—O3 | 84.6 (3) | C9—C8—C7 | 105.1 (9) |
O14—W7—O3 | 74.9 (2) | C9—C8—H8A | 110.7 |
O36—W8—O19 | 101.0 (3) | C7—C8—H8A | 110.7 |
O36—W8—O25 | 96.1 (3) | C9—C8—H8B | 110.7 |
O19—W8—O25 | 92.7 (3) | C7—C8—H8B | 110.7 |
O36—W8—O15 | 101.4 (3) | H8A—C8—H8B | 108.8 |
O19—W8—O15 | 86.9 (3) | C10—C9—C8 | 101.4 (9) |
O25—W8—O15 | 162.2 (3) | C10—C9—H9A | 111.5 |
O36—W8—O21 | 97.8 (3) | C8—C9—H9A | 111.5 |
O19—W8—O21 | 161.1 (3) | C10—C9—H9B | 111.5 |
O25—W8—O21 | 87.4 (3) | C8—C9—H9B | 111.5 |
O15—W8—O21 | 87.3 (3) | H9A—C9—H9B | 109.3 |
O36—W8—O4 | 170.4 (3) | C9—C10—N2 | 104.1 (8) |
O19—W8—O4 | 86.0 (3) | C9—C10—H10A | 110.9 |
O25—W8—O4 | 76.9 (3) | N2—C10—H10A | 110.9 |
O15—W8—O4 | 85.4 (3) | C9—C10—H10B | 110.9 |
O21—W8—O4 | 75.6 (3) | N2—C10—H10B | 110.9 |
O37—W9—O26 | 101.6 (3) | H10A—C10—H10B | 109.0 |
O37—W9—O20 | 99.3 (3) | O5S—C11—O6S | 125.7 (10) |
O26—W9—O20 | 92.5 (3) | O5S—C11—C12 | 122.1 (10) |
O37—W9—O22 | 100.9 (3) | O6S—C11—C12 | 112.1 (9) |
O26—W9—O22 | 86.7 (3) | C11—C12—N3 | 109.3 (9) |
O20—W9—O22 | 159.5 (3) | C11—C12—C13 | 113.9 (9) |
O37—W9—O16 | 97.7 (3) | N3—C12—C13 | 104.1 (9) |
O26—W9—O16 | 160.2 (3) | C11—C12—H12A | 109.8 |
O20—W9—O16 | 88.7 (3) | N3—C12—H12A | 109.8 |
O22—W9—O16 | 85.3 (3) | C13—C12—H12A | 109.8 |
O37—W9—O2 | 171.1 (3) | C12—C13—C14 | 104.4 (9) |
O26—W9—O2 | 86.1 (3) | C12—C13—H13A | 110.9 |
O20—W9—O2 | 75.6 (3) | C14—C13—H13A | 110.9 |
O22—W9—O2 | 83.9 (3) | C12—C13—H13B | 110.9 |
O16—W9—O2 | 75.1 (3) | C14—C13—H13B | 110.9 |
O38—W10—O17 | 100.6 (3) | H13A—C13—H13B | 108.9 |
O38—W10—O23 | 101.2 (3) | C15—C14—C13 | 101.0 (9) |
O17—W10—O23 | 86.7 (3) | C15—C14—H14A | 111.6 |
O38—W10—O27 | 98.1 (3) | C13—C14—H14A | 111.6 |
O17—W10—O27 | 161.2 (3) | C15—C14—H14B | 111.6 |
O23—W10—O27 | 88.2 (3) | C13—C14—H14B | 111.6 |
O38—W10—O21 | 97.3 (3) | H14A—C14—H14B | 109.4 |
O17—W10—O21 | 90.9 (3) | N3—C15—C14 | 103.6 (9) |
O23—W10—O21 | 161.5 (3) | N3—C15—H15A | 111.0 |
O27—W10—O21 | 88.2 (3) | C14—C15—H15A | 111.0 |
O38—W10—O4 | 170.4 (3) | N3—C15—H15B | 111.0 |
O17—W10—O4 | 86.3 (3) | C14—C15—H15B | 111.0 |
O23—W10—O4 | 85.7 (3) | H15A—C15—H15B | 109.0 |
O27—W10—O4 | 75.3 (3) | O8S—C16—O7S | 125.4 (11) |
O21—W10—O4 | 75.8 (3) | O8S—C16—C17 | 122.2 (11) |
O39—W11—O18 | 99.4 (3) | O7S—C16—C17 | 112.3 (10) |
O39—W11—O22 | 99.7 (3) | C18—C17—C16 | 117.0 (11) |
O18—W11—O22 | 89.5 (3) | C18—C17—N4 | 104.0 (10) |
O39—W11—O24 | 99.6 (3) | C16—C17—N4 | 110.1 (10) |
O18—W11—O24 | 88.6 (3) | C18—C17—H17A | 108.5 |
O22—W11—O24 | 160.6 (3) | C16—C17—H17A | 108.5 |
O39—W11—O28 | 99.8 (3) | N4—C17—H17A | 108.5 |
O18—W11—O28 | 160.8 (3) | C17—C18—C19 | 102.7 (11) |
O22—W11—O28 | 87.2 (3) | C17—C18—H18A | 111.2 |
O24—W11—O28 | 88.2 (3) | C19—C18—H18A | 111.2 |
O39—W11—O3 | 173.6 (3) | C17—C18—H18B | 111.2 |
O18—W11—O3 | 75.9 (3) | C19—C18—H18B | 111.2 |
O22—W11—O3 | 84.8 (3) | H18A—C18—H18B | 109.1 |
O24—W11—O3 | 76.0 (3) | C20—C19—C18 | 105.0 (13) |
O28—W11—O3 | 84.9 (3) | C20—C19—H19A | 110.8 |
O40—W12—O28 | 100.3 (4) | C18—C19—H19A | 110.8 |
O40—W12—O27 | 99.0 (3) | C20—C19—H19B | 110.8 |
O28—W12—O27 | 89.8 (3) | C18—C19—H19B | 110.8 |
O40—W12—O26 | 101.7 (3) | H19A—C19—H19B | 108.8 |
O28—W12—O26 | 87.1 (3) | C19—C20—N4 | 105.7 (11) |
O27—W12—O26 | 159.3 (3) | C19—C20—H20A | 110.6 |
O40—W12—O25 | 98.8 (3) | N4—C20—H20A | 110.6 |
O28—W12—O25 | 160.9 (3) | C19—C20—H20B | 110.6 |
O27—W12—O25 | 87.9 (3) | N4—C20—H20B | 110.6 |
O26—W12—O25 | 88.4 (3) | H20A—C20—H20B | 108.7 |
O40—W12—O4 | 171.8 (3) | O10S—C21—O9S | 126.1 (11) |
O28—W12—O4 | 85.5 (3) | O10S—C21—C22 | 123.8 (11) |
O27—W12—O4 | 75.0 (3) | O9S—C21—C22 | 110.0 (10) |
O26—W12—O4 | 84.3 (3) | N5—C22—C23 | 106.1 (11) |
O25—W12—O4 | 75.7 (3) | N5—C22—C21 | 109.2 (10) |
O3—B1—O4 | 110.3 (8) | C23—C22—C21 | 111.5 (13) |
O3—B1—O1 | 111.0 (7) | N5—C22—H22A | 110.0 |
O4—B1—O1 | 110.0 (7) | C23—C22—H22A | 110.0 |
O3—B1—O2 | 108.8 (7) | C21—C22—H22A | 110.0 |
O4—B1—O2 | 108.0 (7) | C24—C23—C22 | 106.9 (12) |
O1—B1—O2 | 108.6 (7) | C24—C23—H23A | 110.4 |
B1—O1—W4 | 124.8 (5) | C22—C23—H23A | 110.4 |
B1—O1—W1 | 125.5 (5) | C24—C23—H23B | 110.3 |
W4—O1—W1 | 90.4 (2) | C22—C23—H23B | 110.3 |
B1—O1—W2 | 126.0 (5) | H23A—C23—H23B | 108.6 |
W4—O1—W2 | 89.0 (2) | C23—C24—C25 | 104.0 (11) |
W1—O1—W2 | 89.8 (2) | C23—C24—H24A | 111.0 |
C1—O1S—H1O | 120.6 | C25—C24—H24A | 111.0 |
B1—O2—W6 | 126.5 (5) | C23—C24—H24B | 110.9 |
B1—O2—W9 | 125.5 (6) | C25—C24—H24B | 111.0 |
W6—O2—W9 | 89.5 (2) | H24A—C24—H24B | 109.0 |
B1—O2—W3 | 125.8 (5) | N5—C25—C24 | 101.4 (10) |
W6—O2—W3 | 89.0 (2) | N5—C25—H25A | 111.5 |
W9—O2—W3 | 88.7 (2) | C24—C25—H25A | 111.5 |
B1—O3—W11 | 127.6 (6) | N5—C25—H25B | 111.5 |
B1—O3—W5 | 125.7 (5) | C24—C25—H25B | 111.5 |
W11—O3—W5 | 89.5 (2) | H25A—C25—H25B | 109.3 |
O3—B1—O1—W4 | 59.2 (8) | O20—W6—O10—W3 | 74.5 (5) |
O4—B1—O1—W4 | −63.2 (8) | O2—W6—O10—W3 | −1.7 (4) |
O2—B1—O1—W4 | 178.8 (4) | O31—W3—O10—W6 | −175.4 (5) |
O3—B1—O1—W1 | −61.3 (9) | O16—W3—O10—W6 | −73.6 (5) |
O4—B1—O1—W1 | 176.3 (5) | O12—W3—O10—W6 | 15.1 (13) |
O2—B1—O1—W1 | 58.4 (8) | O5—W3—O10—W6 | 86.0 (5) |
O3—B1—O1—W2 | 177.8 (5) | O2—W3—O10—W6 | 1.7 (4) |
O4—B1—O1—W2 | 55.4 (9) | O30—W2—O11—W4 | 171.1 (4) |
O2—B1—O1—W2 | −62.6 (8) | O15—W2—O11—W4 | −85.7 (4) |
O32—W4—O1—B1 | 174.8 (15) | O9—W2—O11—W4 | 3.1 (11) |
O13—W4—O1—B1 | −41.5 (6) | O6—W2—O11—W4 | 75.0 (4) |
O17—W4—O1—B1 | 46.5 (6) | O1—W2—O11—W4 | 0.0 (3) |
O7—W4—O1—B1 | −134.6 (6) | O32—W4—O11—W2 | −173.5 (4) |
O11—W4—O1—B1 | 134.8 (6) | O13—W4—O11—W2 | 12.4 (12) |
O32—W4—O1—W1 | −49.8 (16) | O17—W4—O11—W2 | 85.9 (4) |
O13—W4—O1—W1 | 94.0 (3) | O7—W4—O11—W2 | −76.1 (4) |
O17—W4—O1—W1 | −178.1 (3) | O1—W4—O11—W2 | 0.0 (3) |
O7—W4—O1—W1 | 0.9 (2) | O31—W3—O12—W5 | −130.1 (8) |
O11—W4—O1—W1 | −89.8 (3) | O16—W3—O12—W5 | 127.8 (8) |
O32—W4—O1—W2 | 40.0 (16) | O10—W3—O12—W5 | 39.3 (15) |
O13—W4—O1—W2 | −176.3 (3) | O5—W3—O12—W5 | −31.4 (8) |
O17—W4—O1—W2 | −88.3 (3) | O2—W3—O12—W5 | 52.3 (8) |
O7—W4—O1—W2 | 90.6 (3) | O33—W5—O12—W3 | 133.7 (8) |
O11—W4—O1—W2 | 0.0 (2) | O8—W5—O12—W3 | 32.2 (8) |
O29—W1—O1—B1 | 170.5 (16) | O14—W5—O12—W3 | −56.8 (15) |
O5—W1—O1—B1 | −41.8 (6) | O18—W5—O12—W3 | −129.4 (9) |
O8—W1—O1—B1 | 46.6 (6) | O3—W5—O12—W3 | −54.4 (8) |
O6—W1—O1—B1 | −134.6 (7) | O32—W4—O13—W7 | −135.7 (8) |
O7—W1—O1—B1 | 134.1 (7) | O17—W4—O13—W7 | −35.1 (8) |
O29—W1—O1—W4 | 35.6 (18) | O7—W4—O13—W7 | 126.1 (8) |
O5—W1—O1—W4 | −176.7 (3) | O11—W4—O13—W7 | 38.3 (15) |
O8—W1—O1—W4 | −88.3 (3) | O1—W4—O13—W7 | 50.3 (8) |
O6—W1—O1—W4 | 90.5 (3) | O35—W7—O13—W4 | 136.8 (8) |
O7—W1—O1—W4 | −0.9 (2) | O23—W7—O13—W4 | 34.5 (8) |
O29—W1—O1—W2 | −53.4 (18) | O24—W7—O13—W4 | −48.9 (13) |
O5—W1—O1—W2 | 94.3 (3) | O14—W7—O13—W4 | −125.6 (8) |
O8—W1—O1—W2 | −177.3 (3) | O3—W7—O13—W4 | −50.5 (8) |
O6—W1—O1—W2 | 1.5 (3) | O33—W5—O14—W7 | 170.9 (4) |
O7—W1—O1—W2 | −89.9 (3) | O8—W5—O14—W7 | −87.0 (4) |
O15—W2—O1—B1 | −37.9 (6) | O12—W5—O14—W7 | 1.3 (12) |
O11—W2—O1—B1 | −133.8 (7) | O18—W5—O14—W7 | 73.6 (4) |
O9—W2—O1—B1 | 47.3 (6) | O3—W5—O14—W7 | −1.1 (4) |
O6—W2—O1—B1 | 134.3 (7) | O35—W7—O14—W5 | −172.1 (4) |
O15—W2—O1—W4 | 95.9 (3) | O23—W7—O14—W5 | 15.0 (12) |
O11—W2—O1—W4 | 0.0 (2) | O24—W7—O14—W5 | −74.0 (4) |
O9—W2—O1—W4 | −178.9 (3) | O13—W7—O14—W5 | 86.2 (4) |
O6—W2—O1—W4 | −91.9 (3) | O3—W7—O14—W5 | 1.1 (4) |
O15—W2—O1—W1 | −173.6 (3) | O30—W2—O15—W8 | −136.4 (8) |
O11—W2—O1—W1 | 90.4 (3) | O11—W2—O15—W8 | 121.0 (8) |
O9—W2—O1—W1 | −88.4 (3) | O9—W2—O15—W8 | −37.7 (8) |
O6—W2—O1—W1 | −1.5 (3) | O6—W2—O15—W8 | 22.3 (15) |
O3—B1—O2—W6 | 178.6 (5) | O1—W2—O15—W8 | 45.4 (8) |
O4—B1—O2—W6 | −61.6 (9) | O36—W8—O15—W2 | 139.6 (8) |
O1—B1—O2—W6 | 57.6 (8) | O19—W8—O15—W2 | 39.0 (8) |
O3—B1—O2—W9 | −60.4 (8) | O25—W8—O15—W2 | −50.1 (15) |
O4—B1—O2—W9 | 59.4 (9) | O21—W8—O15—W2 | −123.0 (8) |
O1—B1—O2—W9 | 178.6 (4) | O4—W8—O15—W2 | −47.2 (8) |
O3—B1—O2—W3 | 58.2 (9) | O31—W3—O16—W9 | 170.8 (4) |
O4—B1—O2—W3 | 178.0 (5) | O12—W3—O16—W9 | −88.3 (5) |
O1—B1—O2—W3 | −62.8 (8) | O10—W3—O16—W9 | 71.4 (4) |
O9—W6—O2—B1 | −40.3 (7) | O5—W3—O16—W9 | −5.5 (11) |
O10—W6—O2—B1 | −134.4 (7) | O2—W3—O16—W9 | −3.3 (4) |
O19—W6—O2—B1 | 47.2 (7) | O37—W9—O16—W3 | −171.4 (4) |
O20—W6—O2—B1 | 134.5 (7) | O26—W9—O16—W3 | 21.5 (12) |
O9—W6—O2—W9 | −176.1 (3) | O20—W9—O16—W3 | −72.2 (5) |
O10—W6—O2—W9 | 89.9 (3) | O22—W9—O16—W3 | 88.2 (5) |
O19—W6—O2—W9 | −88.6 (3) | O2—W9—O16—W3 | 3.3 (4) |
O20—W6—O2—W9 | −1.2 (2) | O38—W10—O17—W4 | −135.0 (8) |
O9—W6—O2—W3 | 95.2 (3) | O23—W10—O17—W4 | −34.2 (8) |
O10—W6—O2—W3 | 1.2 (3) | O27—W10—O17—W4 | 40.5 (15) |
O19—W6—O2—W3 | −177.3 (3) | O21—W10—O17—W4 | 127.4 (8) |
O20—W6—O2—W3 | −89.9 (3) | O4—W10—O17—W4 | 51.7 (8) |
O26—W9—O2—B1 | −41.6 (6) | O32—W4—O17—W10 | 135.2 (8) |
O20—W9—O2—B1 | −135.2 (6) | O13—W4—O17—W10 | 34.6 (8) |
O22—W9—O2—B1 | 45.5 (6) | O7—W4—O17—W10 | −55.9 (14) |
O16—W9—O2—B1 | 132.3 (6) | O11—W4—O17—W10 | −128.5 (8) |
O26—W9—O2—W6 | 94.8 (3) | O1—W4—O17—W10 | −52.8 (8) |
O20—W9—O2—W6 | 1.2 (2) | O39—W11—O18—W5 | 171.9 (4) |
O22—W9—O2—W6 | −178.0 (3) | O22—W11—O18—W5 | −88.3 (4) |
O16—W9—O2—W6 | −91.3 (3) | O24—W11—O18—W5 | 72.4 (4) |
O26—W9—O2—W3 | −176.2 (3) | O28—W11—O18—W5 | −8.0 (12) |
O20—W9—O2—W3 | 90.2 (3) | O3—W11—O18—W5 | −3.6 (4) |
O22—W9—O2—W3 | −89.0 (3) | O33—W5—O18—W11 | −169.4 (4) |
O16—W9—O2—W3 | −2.3 (3) | O8—W5—O18—W11 | 16.9 (12) |
O16—W3—O2—B1 | −132.1 (7) | O14—W5—O18—W11 | −72.5 (4) |
O12—W3—O2—B1 | −40.4 (7) | O12—W5—O18—W11 | 88.9 (5) |
O10—W3—O2—B1 | 134.9 (7) | O3—W5—O18—W11 | 3.5 (4) |
O5—W3—O2—B1 | 47.1 (7) | O36—W8—O19—W6 | −135.2 (7) |
O16—W3—O2—W6 | 91.8 (3) | O25—W8—O19—W6 | 128.0 (7) |
O12—W3—O2—W6 | −176.5 (3) | O15—W8—O19—W6 | −34.3 (7) |
O10—W3—O2—W6 | −1.2 (3) | O21—W8—O19—W6 | 38.0 (14) |
O5—W3—O2—W6 | −89.0 (3) | O4—W8—O19—W6 | 51.4 (7) |
O16—W3—O2—W9 | 2.3 (3) | O34—W6—O19—W8 | 134.3 (7) |
O12—W3—O2—W9 | 93.9 (3) | O9—W6—O19—W8 | 33.4 (7) |
O10—W3—O2—W9 | −90.7 (3) | O10—W6—O19—W8 | −58.1 (14) |
O5—W3—O2—W9 | −178.5 (3) | O20—W6—O19—W8 | −129.7 (7) |
O4—B1—O3—W11 | −58.8 (9) | O2—W6—O19—W8 | −53.3 (7) |
O1—B1—O3—W11 | 179.0 (5) | O37—W9—O20—W6 | 170.9 (4) |
O2—B1—O3—W11 | 59.6 (9) | O26—W9—O20—W6 | −87.0 (4) |
O4—B1—O3—W5 | 178.4 (5) | O22—W9—O20—W6 | 0.4 (11) |
O1—B1—O3—W5 | 56.2 (9) | O16—W9—O20—W6 | 73.3 (4) |
O2—B1—O3—W5 | −63.3 (9) | O2—W9—O20—W6 | −1.7 (3) |
O4—B1—O3—W7 | 61.2 (9) | O34—W6—O20—W9 | −173.6 (4) |
O1—B1—O3—W7 | −61.0 (9) | O9—W6—O20—W9 | 18.3 (12) |
O2—B1—O3—W7 | 179.5 (5) | O10—W6—O20—W9 | −75.5 (4) |
O18—W11—O3—B1 | −134.5 (7) | O19—W6—O20—W9 | 87.4 (4) |
O22—W11—O3—B1 | −43.6 (7) | O2—W6—O20—W9 | 1.7 (3) |
O24—W11—O3—B1 | 133.5 (7) | O38—W10—O21—W8 | 170.6 (4) |
O28—W11—O3—B1 | 44.1 (7) | O17—W10—O21—W8 | −88.6 (4) |
O18—W11—O3—W5 | 2.5 (3) | O23—W10—O21—W8 | −6.3 (13) |
O22—W11—O3—W5 | 93.4 (3) | O27—W10—O21—W8 | 72.7 (4) |
O24—W11—O3—W5 | −89.5 (3) | O4—W10—O21—W8 | −2.6 (4) |
O28—W11—O3—W5 | −178.9 (3) | O36—W8—O21—W10 | −170.4 (4) |
O18—W11—O3—W7 | 90.8 (3) | O19—W8—O21—W10 | 16.3 (12) |
O22—W11—O3—W7 | −178.4 (3) | O25—W8—O21—W10 | −74.5 (4) |
O24—W11—O3—W7 | −1.3 (2) | O15—W8—O21—W10 | 88.5 (4) |
O28—W11—O3—W7 | −90.7 (3) | O4—W8—O21—W10 | 2.6 (4) |
O33—W5—O3—B1 | 178.2 (15) | O37—W9—O22—W11 | 132.3 (8) |
O8—W5—O3—B1 | −39.8 (7) | O26—W9—O22—W11 | 31.2 (8) |
O14—W5—O3—B1 | −132.5 (7) | O20—W9—O22—W11 | −57.2 (14) |
O12—W5—O3—B1 | 48.4 (7) | O16—W9—O22—W11 | −130.7 (8) |
O18—W5—O3—B1 | 135.8 (7) | O2—W9—O22—W11 | −55.2 (8) |
O33—W5—O3—W11 | 39.9 (17) | O39—W11—O22—W9 | −130.6 (8) |
O8—W5—O3—W11 | −178.1 (3) | O18—W11—O22—W9 | 129.9 (8) |
O14—W5—O3—W11 | 89.3 (3) | O24—W11—O22—W9 | 45.6 (15) |
O12—W5—O3—W11 | −89.9 (3) | O28—W11—O22—W9 | −31.1 (8) |
O18—W5—O3—W11 | −2.5 (3) | O3—W11—O22—W9 | 54.0 (8) |
O33—W5—O3—W7 | −48.6 (17) | O35—W7—O23—W10 | −136.8 (9) |
O8—W5—O3—W7 | 93.4 (3) | O24—W7—O23—W10 | 124.2 (9) |
O14—W5—O3—W7 | 0.8 (2) | O13—W7—O23—W10 | −35.5 (9) |
O12—W5—O3—W7 | −178.4 (3) | O14—W7—O23—W10 | 36.0 (16) |
O18—W5—O3—W7 | −91.0 (3) | O3—W7—O23—W10 | 49.4 (9) |
O23—W7—O3—B1 | −42.0 (7) | O38—W10—O23—W7 | 136.3 (9) |
O24—W7—O3—B1 | −135.3 (7) | O17—W10—O23—W7 | 36.1 (9) |
O13—W7—O3—B1 | 44.1 (7) | O27—W10—O23—W7 | −125.8 (9) |
O14—W7—O3—B1 | 133.0 (7) | O21—W10—O23—W7 | −46.9 (17) |
O23—W7—O3—W11 | 94.6 (3) | O4—W10—O23—W7 | −50.5 (9) |
O24—W7—O3—W11 | 1.3 (2) | O35—W7—O24—W11 | 170.8 (4) |
O13—W7—O3—W11 | −179.3 (3) | O23—W7—O24—W11 | −85.8 (4) |
O14—W7—O3—W11 | −90.4 (3) | O13—W7—O24—W11 | −3.5 (11) |
O23—W7—O3—W5 | −175.8 (3) | O14—W7—O24—W11 | 73.1 (4) |
O24—W7—O3—W5 | 90.9 (3) | O3—W7—O24—W11 | −1.8 (3) |
O13—W7—O3—W5 | −89.7 (3) | O39—W11—O24—W7 | −173.3 (4) |
O14—W7—O3—W5 | −0.8 (2) | O18—W11—O24—W7 | −74.0 (4) |
O3—B1—O4—W10 | −62.4 (9) | O22—W11—O24—W7 | 10.6 (11) |
O1—B1—O4—W10 | 60.4 (9) | O28—W11—O24—W7 | 87.1 (4) |
O2—B1—O4—W10 | 178.8 (5) | O3—W11—O24—W7 | 1.9 (3) |
O3—B1—O4—W8 | 176.7 (5) | O36—W8—O25—W12 | 173.2 (4) |
O1—B1—O4—W8 | −60.5 (9) | O19—W8—O25—W12 | −85.4 (4) |
O2—B1—O4—W8 | 57.8 (9) | O15—W8—O25—W12 | 2.8 (13) |
O3—B1—O4—W12 | 55.8 (9) | O21—W8—O25—W12 | 75.6 (4) |
O1—B1—O4—W12 | 178.6 (5) | O4—W8—O25—W12 | −0.2 (4) |
O2—B1—O4—W12 | −63.1 (9) | O40—W12—O25—W8 | −173.7 (4) |
O17—W10—O4—B1 | −43.0 (7) | O28—W12—O25—W8 | 8.4 (13) |
O23—W10—O4—B1 | 43.9 (7) | O27—W12—O25—W8 | −74.9 (4) |
O27—W10—O4—B1 | 133.2 (7) | O26—W12—O25—W8 | 84.7 (5) |
O21—W10—O4—B1 | −134.9 (7) | O4—W12—O25—W8 | 0.2 (4) |
O17—W10—O4—W8 | 93.7 (3) | O37—W9—O26—W12 | −134.3 (9) |
O23—W10—O4—W8 | −179.3 (3) | O20—W9—O26—W12 | 125.6 (9) |
O27—W10—O4—W8 | −90.0 (3) | O22—W9—O26—W12 | −33.9 (9) |
O21—W10—O4—W8 | 1.9 (3) | O16—W9—O26—W12 | 32.6 (16) |
O17—W10—O4—W12 | −177.8 (3) | O2—W9—O26—W12 | 50.2 (9) |
O23—W10—O4—W12 | −90.8 (3) | O40—W12—O26—W9 | 134.5 (9) |
O27—W10—O4—W12 | −1.5 (2) | O28—W12—O26—W9 | 34.6 (9) |
O21—W10—O4—W12 | 90.4 (3) | O27—W12—O26—W9 | −47.3 (14) |
O19—W8—O4—B1 | −42.4 (7) | O25—W12—O26—W9 | −126.9 (9) |
O25—W8—O4—B1 | −136.2 (7) | O4—W12—O26—W9 | −51.2 (9) |
O15—W8—O4—B1 | 44.7 (7) | O40—W12—O27—W10 | 172.1 (4) |
O21—W8—O4—B1 | 133.1 (7) | O28—W12—O27—W10 | −87.6 (4) |
O19—W8—O4—W10 | −177.4 (3) | O26—W12—O27—W10 | −6.2 (11) |
O25—W8—O4—W10 | 88.8 (3) | O25—W12—O27—W10 | 73.5 (4) |
O15—W8—O4—W10 | −90.3 (3) | O4—W12—O27—W10 | −2.2 (3) |
O21—W8—O4—W10 | −1.9 (3) | O38—W10—O27—W12 | −170.7 (4) |
O36—W8—O4—W12 | −43.6 (19) | O17—W10—O27—W12 | 13.8 (12) |
O19—W8—O4—W12 | 93.8 (3) | O23—W10—O27—W12 | 88.3 (4) |
O25—W8—O4—W12 | 0.1 (3) | O21—W10—O27—W12 | −73.5 (4) |
O15—W8—O4—W12 | −179.0 (3) | O4—W10—O27—W12 | 2.2 (3) |
O21—W8—O4—W12 | −90.6 (3) | O40—W12—O28—W11 | −134.7 (9) |
O28—W12—O4—B1 | −40.7 (7) | O27—W12—O28—W11 | 126.2 (9) |
O27—W12—O4—B1 | −131.8 (7) | O26—W12—O28—W11 | −33.3 (9) |
O26—W12—O4—B1 | 46.8 (7) | O25—W12—O28—W11 | 43.2 (16) |
O25—W12—O4—B1 | 136.6 (7) | O4—W12—O28—W11 | 51.2 (9) |
O28—W12—O4—W10 | 92.6 (3) | O39—W11—O28—W12 | 132.2 (9) |
O27—W12—O4—W10 | 1.5 (2) | O18—W11—O28—W12 | −47.9 (15) |
O26—W12—O4—W10 | −179.9 (3) | O22—W11—O28—W12 | 32.8 (9) |
O25—W12—O4—W10 | −90.1 (3) | O24—W11—O28—W12 | −128.3 (9) |
O27—W12—O4—W8 | 91.5 (3) | O3—W11—O28—W12 | −52.2 (9) |
O26—W12—O4—W8 | −89.9 (3) | O2S—C1—C2—N1 | −0.8 (14) |
O25—W12—O4—W8 | −0.1 (3) | O1S—C1—C2—N1 | 179.5 (8) |
O29—W1—O5—W3 | −133.0 (8) | O2S—C1—C2—C3 | 115.8 (12) |
O8—W1—O5—W3 | −31.9 (8) | O1S—C1—C2—C3 | −63.9 (12) |
O6—W1—O5—W3 | 128.7 (8) | C5—N1—C2—C1 | 130.7 (9) |
O7—W1—O5—W3 | 40.0 (15) | C5—N1—C2—C3 | 7.2 (10) |
O1—W1—O5—W3 | 52.6 (8) | C1—C2—C3—C4 | −148.4 (10) |
O31—W3—O5—W1 | 131.8 (8) | N1—C2—C3—C4 | −28.5 (11) |
O16—W3—O5—W1 | −51.9 (13) | C2—C3—C4—C5 | 39.2 (11) |
O12—W3—O5—W1 | 31.4 (8) | C2—N1—C5—C4 | 17.2 (11) |
O10—W3—O5—W1 | −129.4 (8) | C3—C4—C5—N1 | −34.5 (10) |
O2—W3—O5—W1 | −54.1 (8) | O3S—C6—C7—N2 | −8.5 (14) |
O29—W1—O6—W2 | 169.5 (4) | O4S—C6—C7—N2 | 167.8 (8) |
O5—W1—O6—W2 | −88.4 (4) | O3S—C6—C7—C8 | 104.5 (12) |
O8—W1—O6—W2 | 1.6 (12) | O4S—C6—C7—C8 | −79.2 (11) |
O7—W1—O6—W2 | 73.0 (4) | C10—N2—C7—C6 | 119.1 (9) |
O1—W1—O6—W2 | −2.1 (4) | C10—N2—C7—C8 | 0.2 (11) |
O30—W2—O6—W1 | −175.0 (4) | C6—C7—C8—C9 | −90.3 (10) |
O15—W2—O6—W1 | 25.9 (12) | N2—C7—C8—C9 | 25.6 (11) |
O11—W2—O6—W1 | −73.9 (4) | C7—C8—C9—C10 | −42.1 (10) |
O9—W2—O6—W1 | 85.9 (4) | C8—C9—C10—N2 | 41.5 (10) |
O1—W2—O6—W1 | 2.0 (4) | C7—N2—C10—C9 | −26.3 (11) |
O32—W4—O7—W1 | 171.0 (4) | O5S—C11—C12—N3 | −6.5 (14) |
O13—W4—O7—W1 | −87.8 (4) | O6S—C11—C12—N3 | 173.3 (9) |
O17—W4—O7—W1 | 2.0 (12) | O5S—C11—C12—C13 | 109.4 (12) |
O11—W4—O7—W1 | 74.6 (4) | O6S—C11—C12—C13 | −70.8 (12) |
O1—W4—O7—W1 | −1.2 (3) | C15—N3—C12—C11 | 126.8 (9) |
O29—W1—O7—W4 | −172.7 (4) | C15—N3—C12—C13 | 4.8 (10) |
O5—W1—O7—W4 | 14.3 (12) | C11—C12—C13—C14 | −97.9 (10) |
O8—W1—O7—W4 | 86.5 (4) | N3—C12—C13—C14 | 21.0 (10) |
O6—W1—O7—W4 | −75.2 (4) | C12—C13—C14—C15 | −38.3 (10) |
O1—W1—O7—W4 | 1.2 (3) | C12—N3—C15—C14 | −29.4 (11) |
O33—W5—O8—W1 | −134.4 (7) | C13—C14—C15—N3 | 41.0 (10) |
O14—W5—O8—W1 | 128.0 (7) | O8S—C16—C17—C18 | 113.8 (15) |
O12—W5—O8—W1 | −32.4 (7) | O7S—C16—C17—C18 | −65.8 (16) |
O18—W5—O8—W1 | 39.2 (14) | O8S—C16—C17—N4 | −4.7 (16) |
O3—W5—O8—W1 | 52.1 (7) | O7S—C16—C17—N4 | 175.7 (10) |
O29—W1—O8—W5 | 134.2 (7) | C20—N4—C17—C18 | 19.8 (13) |
O5—W1—O8—W5 | 32.7 (7) | C20—N4—C17—C16 | 145.9 (10) |
O6—W1—O8—W5 | −58.0 (13) | C16—C17—C18—C19 | −158.2 (15) |
O7—W1—O8—W5 | −129.7 (7) | N4—C17—C18—C19 | −36.5 (17) |
O1—W1—O8—W5 | −54.4 (7) | C17—C18—C19—C20 | 40 (2) |
O34—W6—O9—W2 | −132.2 (8) | C18—C19—C20—N4 | −27.9 (19) |
O10—W6—O9—W2 | 128.7 (8) | C17—N4—C20—C19 | 5.0 (15) |
O19—W6—O9—W2 | −33.2 (8) | C25—N5—C22—C23 | 24.6 (15) |
O20—W6—O9—W2 | 35.6 (15) | C25—N5—C22—C21 | 144.8 (10) |
O2—W6—O9—W2 | 51.8 (8) | O10S—C21—C22—N5 | −16.2 (18) |
O30—W2—O9—W6 | 135.2 (8) | O9S—C21—C22—N5 | 165.5 (10) |
O15—W2—O9—W6 | 34.0 (8) | O10S—C21—C22—C23 | 100.7 (16) |
O11—W2—O9—W6 | −56.7 (13) | O9S—C21—C22—C23 | −77.7 (15) |
O6—W2—O9—W6 | −129.1 (8) | N5—C22—C23—C24 | −1 (2) |
O1—W2—O9—W6 | −53.7 (8) | C21—C22—C23—C24 | −119.4 (14) |
O34—W6—O10—W3 | 170.8 (5) | C22—C23—C24—C25 | −23.2 (19) |
O9—W6—O10—W3 | −87.3 (5) | C22—N5—C25—C24 | −38.4 (11) |
O19—W6—O10—W3 | 3.2 (14) | C23—C24—C25—N5 | 37.1 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1NB···O12i | 0.92 | 2.47 | 3.228 (12) | 140 |
N1—H1NB···O16i | 0.92 | 2.51 | 3.059 (11) | 119 |
N1—H1NB···O18i | 0.92 | 2.49 | 3.132 (12) | 128 |
N1—H1NB···O22i | 0.92 | 2.28 | 3.016 (11) | 136 |
O1S—H1O···O38ii | 0.72 | 2.18 | 2.669 (11) | 126 |
N1—H1NA···O2S | 0.92 | 2.24 | 2.725 (12) | 112 |
N1—H1NA···O36iii | 0.92 | 2.01 | 2.855 (12) | 152 |
N2—H2NB···O3S | 0.92 | 2.18 | 2.687 (12) | 114 |
N2—H2NB···O40iv | 0.92 | 1.93 | 2.744 (11) | 146 |
N2—H2NA···O6v | 0.92 | 1.90 | 2.810 (11) | 170 |
O4S—H4O···O3W | 0.92 | 1.73 | 2.647 (12) | 170 |
N3—H3NB···O3Sii | 0.92 | 2.18 | 2.909 (13) | 135 |
N3—H3NA···O5S | 0.92 | 2.16 | 2.672 (11) | 114 |
N3—H3NA···O10S | 0.92 | 2.05 | 2.856 (12) | 145 |
O6S—H6O···O1W | 0.84 | 1.88 | 2.638 (13) | 149 |
N4—H4NB···O7 | 0.92 | 1.96 | 2.821 (13) | 155 |
O7S—H7O···O21vi | 0.84 | 1.87 | 2.689 (11) | 165 |
N4—H4NA···O8S | 0.92 | 2.29 | 2.701 (13) | 107 |
N5—H5NB···O10S | 0.92 | 2.26 | 2.709 (12) | 109 |
N5—H5NB···O25i | 0.92 | 2.20 | 3.005 (11) | 146 |
O9S—H9O···O2W | 0.89 | 1.86 | 2.651 (12) | 147 |
N5—H5NA···O31 | 0.92 | 2.25 | 2.830 (12) | 120 |
N5—H5NA···O8Svii | 0.92 | 2.00 | 2.855 (13) | 154 |
Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) x−1/2, −y+3/2, −z+1; (iii) x, y, z+1; (iv) −x+2, y+1/2, −z+1/2; (v) −x+1, y+1/2, −z+1/2; (vi) x−1/2, −y+3/2, −z; (vii) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | (C5H10NO2)5[BW12O40]·3H2O |
Mr | 3491.76 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 100 |
a, b, c (Å) | 12.9135 (3), 21.6013 (5), 22.2343 (5) |
V (Å3) | 6202.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 22.27 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (APEX2; Bruker, 2005) |
Tmin, Tmax | 0.084, 0.110 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 95451, 16473, 15774 |
Rint | 0.078 |
(sin θ/λ)max (Å−1) | 0.682 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.088, 1.07 |
No. of reflections | 16473 |
No. of parameters | 865 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 3.37, −1.04 |
Absolute structure | Flack (1983), 7492 Friedel pairs |
Absolute structure parameter | 0.008 (10) |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1NB···O12i | 0.92 | 2.47 | 3.228 (12) | 140 |
N1—H1NB···O16i | 0.92 | 2.51 | 3.059 (11) | 119 |
N1—H1NB···O18i | 0.92 | 2.49 | 3.132 (12) | 128 |
N1—H1NB···O22i | 0.92 | 2.28 | 3.016 (11) | 136 |
O1S—H1O···O38ii | 0.72 | 2.18 | 2.669 (11) | 126 |
N1—H1NA···O2S | 0.92 | 2.24 | 2.725 (12) | 112 |
N1—H1NA···O36iii | 0.92 | 2.01 | 2.855 (12) | 152 |
N2—H2NB···O3S | 0.92 | 2.18 | 2.687 (12) | 114 |
N2—H2NB···O40iv | 0.92 | 1.93 | 2.744 (11) | 146 |
N2—H2NA···O6v | 0.92 | 1.90 | 2.810 (11) | 170 |
O4S—H4O···O3W | 0.92 | 1.73 | 2.647 (12) | 170 |
N3—H3NB···O3Sii | 0.92 | 2.18 | 2.909 (13) | 135 |
N3—H3NA···O5S | 0.92 | 2.16 | 2.672 (11) | 114 |
N3—H3NA···O10S | 0.92 | 2.05 | 2.856 (12) | 145 |
O6S—H6O···O1W | 0.84 | 1.88 | 2.638 (13) | 149 |
N4—H4NB···O7 | 0.92 | 1.96 | 2.821 (13) | 155 |
O7S—H7O···O21vi | 0.84 | 1.87 | 2.689 (11) | 165 |
N4—H4NA···O8S | 0.92 | 2.29 | 2.701 (13) | 107 |
N5—H5NB···O10S | 0.92 | 2.26 | 2.709 (12) | 109 |
N5—H5NB···O25i | 0.92 | 2.20 | 3.005 (11) | 146 |
O9S—H9O···O2W | 0.89 | 1.86 | 2.651 (12) | 147 |
N5—H5NA···O31 | 0.92 | 2.25 | 2.830 (12) | 120 |
N5—H5NA···O8Svii | 0.92 | 2.00 | 2.855 (13) | 154 |
Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) x−1/2, −y+3/2, −z+1; (iii) x, y, z+1; (iv) −x+2, y+1/2, −z+1/2; (v) −x+1, y+1/2, −z+1/2; (vi) x−1/2, −y+3/2, −z; (vii) −x+1, y−1/2, −z+1/2. |
Acknowledgements
Support of this investigation by Islamic Azad University-North Tehran Branch is gratefully acknowledged.
References
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Pourayoubi, M. & Mahjoub, A. R. (2007). Acta Cryst. E63, m2622–m2623. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pourayoubi, M., Mahjoub, A. R., Maleki, F., Ghammamy, S. & Lavaee, P. (2008). J. Iran. Chem. Soc. 5, 588–594. CrossRef CAS Google Scholar
Rocchiccioli-Deltcheff, C., Fournier, M., Franck, R. & Thouvenot, R. (1983). Inorg. Chem. 22, 207–216. CrossRef CAS Web of Science Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Continuing our previous studies on synthesis and X-ray structure determination of some PX12O403--based (X = Mo, W) organic inorganic hybrid compounds such as (C8H10N5)[H2PMo12O40].2.5CH3OH.4H2O (Pourayoubi & Mahjoub, 2007) and [CH3CH2C(OH)+NHCH3]3[PW12O40].0.5CH3CH2C(O)NHCH3.2H2O (Pourayoubi et al., 2008), we report here on the synthesis and crystal structure of a new hybrid material containing a [BW12O40]5- polyoxoanion.
The title polyoxometalate-based organic-inorganic hybrid compound consists of one [BW12O40]5- polyoxoanion, five crystallographically independent L-prolinium cations and three crystal water molecules. The inorganic anion shows a classical α-Keggin structure (Fig. 1) with 4 different types of O atoms. This includes 12 terminal O atoms, 4 O atoms that are bonded to B and W atoms, 12 corner-sharing and 12 edge-sharing O atoms that both are part of distorted WO6 octahedra. The central BO4 tetrahedron is slightly distorted and is surrounded by 12 distorted WO6 octahedra. The B—O bond lengths range from 1.503 (12) to 1.556 (12) Å, and the O—B—O angles are in the range of 108.0 (7)–111.0 (7)°.
All five organic cations (Fig. 2) show slight differences in bond lengths, angles and torsion angles. They are involved in an extensive hydrogen bonding. Several N—H···O (N···O distances are in the range of 2.672 (11) to 3.228 (12) Å) and O—H···O (O···O distances are in the range from 2.638 (13) to 2.689 (11) Å) hydrogen bonds between the organic cations, inorganic anions and crystal water molecules lead to a 3-D supramolecular framework.