Lagoden (
L·3H
2O, where
L is Na
+·C
20H
33O
6-; sodium 3
,16,18-trihydroxy-8,13-
epi-9,13-epoxylabdan-15-oate trihydrate) is widely used as an effective haemostatic agent. It has been crystallized from dimethylformamide (DMF) as sodium 3
,16,18-trihydroxy-8,13-
epi-9,13-epoxylabdan-15-oate dimethylformamide hemisolvate dihydrate, Na
+·C
20H
33O
6-·0.5C
3H
7NO·2H
2O or
L2·DMF·4H
2O, and the asymmetric unit contains two of the latter formulation. The four symmetry-independent Na
+ cations and lagoden anions, one DMF molecule and six of the eight symmetry-independent water molecules assemble into a one-dimensional polymeric structure
via dipolar and hydrogen-bonding interactions. The lagoden anions coordinate to the Na
+ cations
via the carboxylate groups and the two primary hydroxy groups, whereas the secondary OH groups are solely involved in hydrogen bonding. Two of the four symmetry-independent lagoden anions act in a chelating mode, forming seven-membered chelate rings. The absolute structure, based on anomalous dispersion data collected at 130 K with Cu
K radiation, confirms an inverted configuration at chiral centres C8 and C13 (labdane numbering) relative to the labdane skeleton.
Supporting information
CCDC reference: 755968
Lagoden [Source?] (1.2 mg) was dissolved in DMF (1 ml) and placed in a
1.5 ml closed plastic vial. After approximately three months, one colourless
prism-shaped crystal of (I) was obtained.
C-bound H atoms were placed in idealized positions, with C—H = 0.93–0.98 Å. O-bound H atoms were located in difference electron-density maps and
refined with distance restraints of O—H = 0.82 (2) Å for hydroxyl groups
and 0.85 (2) Å for water molecules. The H···H distances in the water
molecules were restrained to 1.35 (2) Å. In the final cycles of refinement,
all the H atoms were treated as riding on their parent atoms, with
Uiso(H) = 1.2Ueq(C,O).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
sodium 3
β,16,18-trihydroxy-8,13-
epi-9,13-epoxylabdan-15-oate
dimethylformamide hemisolvate dihydrate
top
Crystal data top
Na+·C20H33O6−·0.5C3H7NO·2H2O | F(000) = 2016 |
Mr = 465.04 | Dx = 1.345 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P 2yb | Cell parameters from 58666 reflections |
a = 10.7614 (2) Å | θ = 4.3–76.3° |
b = 31.0703 (5) Å | µ = 1.01 mm−1 |
c = 14.7131 (3) Å | T = 130 K |
β = 110.948 (2)° | Prism, colourless |
V = 4594.32 (15) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 8 | |
Data collection top
Oxford Diffraction SuperNova diffractometer | 18050 independent reflections |
Radiation source: Nova Cu X-ray source | 17865 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
ω scans | θmax = 76.5°, θmin = 4.4° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | h = −13→13 |
Tmin = 0.655, Tmax = 0.818 | k = −38→33 |
70056 measured reflections | l = −17→18 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0545P)2 + 1.3939P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.086 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.55 e Å−3 |
18050 reflections | Δρmin = −0.29 e Å−3 |
1143 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.00094 (13) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 8192 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.03 (3) |
Crystal data top
Na+·C20H33O6−·0.5C3H7NO·2H2O | V = 4594.32 (15) Å3 |
Mr = 465.04 | Z = 8 |
Monoclinic, P21 | Cu Kα radiation |
a = 10.7614 (2) Å | µ = 1.01 mm−1 |
b = 31.0703 (5) Å | T = 130 K |
c = 14.7131 (3) Å | 0.3 × 0.2 × 0.2 mm |
β = 110.948 (2)° | |
Data collection top
Oxford Diffraction SuperNova diffractometer | 18050 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 17865 reflections with I > 2σ(I) |
Tmin = 0.655, Tmax = 0.818 | Rint = 0.030 |
70056 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.086 | Δρmax = 0.55 e Å−3 |
S = 1.03 | Δρmin = −0.29 e Å−3 |
18050 reflections | Absolute structure: Flack (1983), with 8192 Friedel pairs |
1143 parameters | Absolute structure parameter: 0.03 (3) |
1 restraint | |
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 | |
Na1 | −0.10902 (8) | 0.75631 (3) | 0.50850 (6) | 0.03321 (17) | |
Na2 | 0.27294 (6) | 0.70357 (2) | 0.61866 (4) | 0.01765 (13) | |
Na3 | 0.61256 (6) | 0.72253 (2) | 0.68407 (4) | 0.01754 (13) | |
Na4 | 1.00891 (7) | 0.72153 (2) | 0.79370 (5) | 0.02417 (14) | |
O1A | 1.14501 (12) | 0.61649 (4) | 0.28884 (9) | 0.0240 (3) | |
H1A | 1.2036 | 0.6314 | 0.3267 | 0.029* | |
O2A | 1.12672 (12) | 0.65194 (4) | 0.51415 (9) | 0.0244 (3) | |
H2OA | 1.0637 | 0.6491 | 0.5325 | 0.029* | |
O3A | 0.69893 (10) | 0.61338 (3) | 0.42628 (8) | 0.0148 (2) | |
O4A | 0.67641 (12) | 0.69657 (4) | 0.34513 (10) | 0.0254 (3) | |
H4A | 0.6529 | 0.7188 | 0.3645 | 0.030* | |
O5A | 0.42888 (11) | 0.69621 (4) | 0.54739 (8) | 0.0192 (2) | |
O6A | 0.33094 (11) | 0.67757 (4) | 0.39154 (8) | 0.0173 (2) | |
C1A | 0.79493 (16) | 0.59460 (6) | 0.26893 (11) | 0.0178 (3) | |
H1A1 | 0.7188 | 0.5856 | 0.2133 | 0.021* | |
H1A2 | 0.7766 | 0.6232 | 0.2874 | 0.021* | |
C2A | 0.91770 (16) | 0.59651 (6) | 0.23946 (11) | 0.0199 (3) | |
H2A1 | 0.9366 | 0.5680 | 0.2207 | 0.024* | |
H2A2 | 0.9002 | 0.6155 | 0.1839 | 0.024* | |
C3A | 1.03653 (15) | 0.61273 (6) | 0.32299 (11) | 0.0175 (3) | |
H3A | 1.0154 | 0.6416 | 0.3400 | 0.021* | |
C4A | 1.07090 (15) | 0.58429 (5) | 0.41434 (11) | 0.0166 (3) | |
C5A | 0.94371 (14) | 0.57600 (5) | 0.43956 (11) | 0.0134 (3) | |
H5A | 0.9239 | 0.6039 | 0.4622 | 0.016* | |
C6A | 0.96823 (16) | 0.54600 (6) | 0.52632 (11) | 0.0187 (3) | |
H6A1 | 1.0503 | 0.5538 | 0.5783 | 0.022* | |
H6A2 | 0.9842 | 0.5168 | 0.5101 | 0.022* | |
C7A | 0.85175 (16) | 0.54788 (6) | 0.56248 (12) | 0.0198 (3) | |
H7A1 | 0.8483 | 0.5763 | 0.5889 | 0.024* | |
H7A2 | 0.8664 | 0.5271 | 0.6146 | 0.024* | |
C8A | 0.71836 (16) | 0.53834 (5) | 0.48175 (12) | 0.0173 (3) | |
H8A | 0.7247 | 0.5092 | 0.4584 | 0.021* | |
C9A | 0.69573 (15) | 0.56911 (5) | 0.39394 (11) | 0.0138 (3) | |
C10A | 0.81274 (15) | 0.56354 (5) | 0.35377 (11) | 0.0140 (3) | |
C11A | 0.55537 (15) | 0.56377 (5) | 0.31686 (12) | 0.0176 (3) | |
H11A | 0.5568 | 0.5682 | 0.2520 | 0.021* | |
H11B | 0.5207 | 0.5353 | 0.3204 | 0.021* | |
C12A | 0.47022 (15) | 0.59838 (5) | 0.34137 (12) | 0.0186 (3) | |
H12A | 0.4010 | 0.6088 | 0.2829 | 0.022* | |
H12B | 0.4294 | 0.5872 | 0.3856 | 0.022* | |
C13A | 0.56962 (15) | 0.63414 (5) | 0.38970 (11) | 0.0155 (3) | |
C14A | 0.55672 (15) | 0.65520 (5) | 0.47925 (11) | 0.0180 (3) | |
H14A | 0.5730 | 0.6331 | 0.5288 | 0.022* | |
H14B | 0.6281 | 0.6761 | 0.5033 | 0.022* | |
C15A | 0.42807 (15) | 0.67786 (5) | 0.47144 (11) | 0.0148 (3) | |
C16A | 0.56747 (16) | 0.66739 (5) | 0.31266 (12) | 0.0194 (3) | |
H16A | 0.5691 | 0.6525 | 0.2551 | 0.023* | |
H16B | 0.4851 | 0.6836 | 0.2945 | 0.023* | |
C17A | 0.60815 (17) | 0.53736 (6) | 0.52475 (13) | 0.0225 (3) | |
H17A | 0.6286 | 0.5159 | 0.5749 | 0.027* | |
H17B | 0.5249 | 0.5306 | 0.4744 | 0.027* | |
H17C | 0.6019 | 0.5650 | 0.5519 | 0.027* | |
C18A | 1.17199 (16) | 0.60974 (6) | 0.49978 (12) | 0.0198 (3) | |
H18A | 1.1911 | 0.5933 | 0.5592 | 0.024* | |
H18B | 1.2544 | 0.6127 | 0.4876 | 0.024* | |
C19A | 1.14154 (16) | 0.54267 (6) | 0.40348 (13) | 0.0229 (3) | |
H19A | 1.0826 | 0.5258 | 0.3510 | 0.027* | |
H19B | 1.1661 | 0.5264 | 0.4628 | 0.027* | |
H19C | 1.2199 | 0.5497 | 0.3898 | 0.027* | |
C20A | 0.81056 (16) | 0.51721 (5) | 0.31567 (12) | 0.0192 (3) | |
H20A | 0.7206 | 0.5091 | 0.2783 | 0.023* | |
H20B | 0.8463 | 0.4979 | 0.3697 | 0.023* | |
H20C | 0.8635 | 0.5158 | 0.2753 | 0.023* | |
O1B | −0.32630 (12) | 0.83552 (5) | 0.28086 (9) | 0.0279 (3) | |
H1B | −0.3491 | 0.8189 | 0.3153 | 0.033* | |
O2B | −0.09882 (12) | 0.83101 (4) | 0.53474 (9) | 0.0254 (3) | |
H2OB | −0.0290 | 0.8391 | 0.5762 | 0.030* | |
O3B | 0.26637 (11) | 0.83842 (3) | 0.42626 (7) | 0.0148 (2) | |
O4B | 0.20911 (12) | 0.75230 (4) | 0.37516 (9) | 0.0216 (2) | |
H4B | 0.2426 | 0.7284 | 0.3896 | 0.026* | |
O5B | 0.67748 (11) | 0.76372 (4) | 0.55902 (9) | 0.0216 (2) | |
O6B | 0.60828 (12) | 0.77376 (4) | 0.39879 (9) | 0.0226 (2) | |
C1B | 0.01308 (16) | 0.84514 (6) | 0.26535 (11) | 0.0195 (3) | |
H1B1 | 0.0392 | 0.8473 | 0.2088 | 0.023* | |
H1B2 | 0.0500 | 0.8187 | 0.2991 | 0.023* | |
C2B | −0.13871 (16) | 0.84297 (6) | 0.23133 (11) | 0.0215 (3) | |
H2B1 | −0.1766 | 0.8687 | 0.1945 | 0.026* | |
H2B2 | −0.1704 | 0.8183 | 0.1889 | 0.026* | |
C3B | −0.18349 (15) | 0.83925 (6) | 0.31762 (12) | 0.0196 (3) | |
H3B | −0.1463 | 0.8126 | 0.3524 | 0.023* | |
C4B | −0.13540 (15) | 0.87692 (6) | 0.38934 (12) | 0.0188 (3) | |
C5B | 0.01940 (15) | 0.88051 (5) | 0.41918 (11) | 0.0149 (3) | |
H5B | 0.0543 | 0.8532 | 0.4518 | 0.018* | |
C6B | 0.08086 (16) | 0.91517 (5) | 0.49604 (12) | 0.0187 (3) | |
H6B1 | 0.0545 | 0.9434 | 0.4675 | 0.022* | |
H6B2 | 0.0481 | 0.9119 | 0.5491 | 0.022* | |
C7B | 0.23235 (16) | 0.91174 (5) | 0.53525 (12) | 0.0185 (3) | |
H7B1 | 0.2696 | 0.9343 | 0.5827 | 0.022* | |
H7B2 | 0.2586 | 0.8843 | 0.5678 | 0.022* | |
C8B | 0.28791 (16) | 0.91566 (5) | 0.45368 (12) | 0.0180 (3) | |
H8B | 0.2557 | 0.9431 | 0.4208 | 0.022* | |
C9B | 0.22981 (15) | 0.87959 (5) | 0.37720 (11) | 0.0148 (3) | |
C10B | 0.07246 (15) | 0.88342 (5) | 0.33341 (11) | 0.0158 (3) | |
C11B | 0.29317 (16) | 0.87950 (5) | 0.29856 (12) | 0.0186 (3) | |
H11C | 0.2281 | 0.8718 | 0.2357 | 0.022* | |
H11D | 0.3293 | 0.9076 | 0.2936 | 0.022* | |
C12B | 0.40445 (16) | 0.84582 (5) | 0.33227 (11) | 0.0184 (3) | |
H12C | 0.4148 | 0.8313 | 0.2770 | 0.022* | |
H12D | 0.4884 | 0.8590 | 0.3709 | 0.022* | |
C13B | 0.35841 (15) | 0.81417 (5) | 0.39378 (11) | 0.0158 (3) | |
C14B | 0.46861 (16) | 0.79859 (5) | 0.48643 (11) | 0.0170 (3) | |
H14C | 0.4979 | 0.8232 | 0.5294 | 0.020* | |
H14D | 0.4285 | 0.7785 | 0.5182 | 0.020* | |
C15B | 0.59307 (16) | 0.77701 (5) | 0.48001 (11) | 0.0165 (3) | |
C16B | 0.28405 (17) | 0.77678 (5) | 0.33052 (12) | 0.0197 (3) | |
H16C | 0.2242 | 0.7879 | 0.2688 | 0.024* | |
H16D | 0.3476 | 0.7580 | 0.3172 | 0.024* | |
C17B | 0.44005 (17) | 0.91845 (6) | 0.49627 (14) | 0.0234 (3) | |
H17D | 0.4664 | 0.9423 | 0.5407 | 0.028* | |
H17E | 0.4736 | 0.9226 | 0.4446 | 0.028* | |
H17F | 0.4755 | 0.8923 | 0.5302 | 0.028* | |
C18B | −0.16969 (16) | 0.86675 (6) | 0.48001 (12) | 0.0234 (4) | |
H18C | −0.1506 | 0.8919 | 0.5218 | 0.028* | |
H18D | −0.2643 | 0.8610 | 0.4598 | 0.028* | |
C19B | −0.21286 (18) | 0.91856 (6) | 0.34781 (14) | 0.0272 (4) | |
H19D | −0.2185 | 0.9224 | 0.2817 | 0.033* | |
H19E | −0.1675 | 0.9427 | 0.3861 | 0.033* | |
H19F | −0.3009 | 0.9165 | 0.3498 | 0.033* | |
C20B | 0.03577 (17) | 0.92573 (6) | 0.27470 (13) | 0.0226 (3) | |
H20D | 0.0917 | 0.9293 | 0.2370 | 0.027* | |
H20E | 0.0484 | 0.9496 | 0.3186 | 0.027* | |
H20F | −0.0556 | 0.9246 | 0.2320 | 0.027* | |
O1C | 0.15096 (11) | 0.60367 (4) | 0.97668 (8) | 0.0189 (2) | |
H1C | 0.0876 | 0.6138 | 0.9322 | 0.023* | |
O2C | 0.13234 (11) | 0.59647 (4) | 0.73474 (8) | 0.0191 (2) | |
H2OC | 0.0888 | 0.6149 | 0.7500 | 0.023* | |
O3C | 0.60861 (10) | 0.58770 (3) | 0.84167 (7) | 0.0134 (2) | |
O4C | 0.60342 (12) | 0.67987 (4) | 0.82647 (9) | 0.0224 (2) | |
H4OC | 0.5537 | 0.6903 | 0.8518 | 0.027* | |
O5C | 0.80957 (11) | 0.68333 (4) | 0.70637 (8) | 0.0182 (2) | |
O6C | 0.96960 (11) | 0.64442 (4) | 0.81103 (9) | 0.0214 (2) | |
C1C | 0.50773 (15) | 0.59593 (5) | 0.99976 (11) | 0.0153 (3) | |
H1C1 | 0.5888 | 0.5989 | 1.0562 | 0.018* | |
H1C2 | 0.5058 | 0.6190 | 0.9549 | 0.018* | |
C2C | 0.38816 (15) | 0.60067 (5) | 1.03217 (11) | 0.0172 (3) | |
H2C1 | 0.3902 | 0.5782 | 1.0784 | 0.021* | |
H2C2 | 0.3921 | 0.6283 | 1.0639 | 0.021* | |
C3C | 0.26038 (14) | 0.59754 (5) | 0.94426 (11) | 0.0138 (3) | |
H3C | 0.2596 | 0.6213 | 0.9001 | 0.017* | |
C4C | 0.24727 (14) | 0.55490 (5) | 0.88726 (11) | 0.0143 (3) | |
C5C | 0.37581 (14) | 0.54763 (5) | 0.86310 (10) | 0.0135 (3) | |
H5C | 0.3757 | 0.5710 | 0.8183 | 0.016* | |
C6C | 0.37228 (16) | 0.50602 (5) | 0.80580 (12) | 0.0199 (3) | |
H6C1 | 0.3763 | 0.4813 | 0.8471 | 0.024* | |
H6C2 | 0.2892 | 0.5046 | 0.7506 | 0.024* | |
C7C | 0.48860 (17) | 0.50450 (6) | 0.76966 (13) | 0.0218 (3) | |
H7C1 | 0.4865 | 0.4774 | 0.7365 | 0.026* | |
H7C2 | 0.4792 | 0.5275 | 0.7231 | 0.026* | |
C8C | 0.62172 (16) | 0.50896 (5) | 0.85269 (12) | 0.0182 (3) | |
H8C | 0.6273 | 0.4854 | 0.8983 | 0.022* | |
C9C | 0.62742 (15) | 0.55160 (5) | 0.90882 (11) | 0.0139 (3) | |
C10C | 0.51073 (15) | 0.55251 (5) | 0.95043 (11) | 0.0141 (3) | |
C11C | 0.76585 (15) | 0.55929 (6) | 0.98688 (11) | 0.0176 (3) | |
H11E | 0.7580 | 0.5732 | 1.0436 | 0.021* | |
H11F | 0.8129 | 0.5323 | 1.0068 | 0.021* | |
C12C | 0.83934 (15) | 0.58849 (6) | 0.93879 (11) | 0.0182 (3) | |
H12E | 0.8919 | 0.5716 | 0.9103 | 0.022* | |
H12F | 0.8976 | 0.6084 | 0.9857 | 0.022* | |
C13C | 0.72794 (14) | 0.61280 (5) | 0.85982 (11) | 0.0141 (3) | |
C14C | 0.74595 (15) | 0.61727 (5) | 0.76134 (11) | 0.0163 (3) | |
H14E | 0.7716 | 0.5895 | 0.7435 | 0.020* | |
H14F | 0.6610 | 0.6250 | 0.7124 | 0.020* | |
C15C | 0.84886 (15) | 0.65047 (5) | 0.75978 (11) | 0.0157 (3) | |
C16C | 0.70955 (15) | 0.65734 (5) | 0.89760 (12) | 0.0177 (3) | |
H16E | 0.6904 | 0.6542 | 0.9569 | 0.021* | |
H16F | 0.7912 | 0.6737 | 0.9129 | 0.021* | |
C17C | 0.73548 (18) | 0.50246 (6) | 0.81462 (14) | 0.0242 (4) | |
H17G | 0.7271 | 0.4747 | 0.7844 | 0.029* | |
H17H | 0.8190 | 0.5042 | 0.8679 | 0.029* | |
H17I | 0.7318 | 0.5244 | 0.7678 | 0.029* | |
C18C | 0.12572 (15) | 0.55982 (5) | 0.79191 (11) | 0.0167 (3) | |
H18E | 0.1180 | 0.5341 | 0.7530 | 0.020* | |
H18F | 0.0460 | 0.5620 | 0.8079 | 0.020* | |
C19C | 0.21264 (17) | 0.51700 (6) | 0.94087 (13) | 0.0212 (3) | |
H19G | 0.2800 | 0.5141 | 1.0043 | 0.025* | |
H19H | 0.2081 | 0.4910 | 0.9046 | 0.025* | |
H19I | 0.1281 | 0.5222 | 0.9472 | 0.025* | |
C20C | 0.53759 (16) | 0.51619 (6) | 1.02722 (12) | 0.0206 (3) | |
H20G | 0.6305 | 0.5157 | 1.0666 | 0.025* | |
H20H | 0.5126 | 0.4890 | 0.9949 | 0.025* | |
H20I | 0.4863 | 0.5213 | 1.0678 | 0.025* | |
O1D | 1.32037 (11) | 0.84302 (4) | 0.94695 (8) | 0.0201 (2) | |
H1D | 1.3376 | 0.8325 | 0.9018 | 0.024* | |
O2D | 1.10866 (11) | 0.84948 (4) | 0.70680 (8) | 0.0180 (2) | |
H2OD | 1.1652 | 0.8305 | 0.7232 | 0.022* | |
O3D | 0.73293 (10) | 0.85953 (3) | 0.81794 (7) | 0.0128 (2) | |
O4D | 0.75227 (11) | 0.76864 (4) | 0.82348 (9) | 0.0198 (2) | |
H4OD | 0.7992 | 0.7852 | 0.8064 | 0.024* | |
O5D | 0.43126 (11) | 0.75662 (4) | 0.70699 (8) | 0.0201 (2) | |
O6D | 0.33128 (12) | 0.80146 (4) | 0.77681 (9) | 0.0227 (2) | |
C1D | 0.99117 (15) | 0.85461 (5) | 0.97734 (11) | 0.0159 (3) | |
H1D1 | 0.9688 | 0.8537 | 1.0356 | 0.019* | |
H1D2 | 0.9480 | 0.8303 | 0.9369 | 0.019* | |
C2D | 1.14156 (15) | 0.84990 (5) | 1.00635 (11) | 0.0168 (3) | |
H2D1 | 1.1859 | 0.8733 | 1.0493 | 0.020* | |
H2D2 | 1.1702 | 0.8230 | 1.0412 | 0.020* | |
C3D | 1.17958 (14) | 0.85034 (5) | 0.91688 (11) | 0.0149 (3) | |
H3D | 1.1341 | 0.8262 | 0.8753 | 0.018* | |
C4D | 1.13631 (14) | 0.89222 (5) | 0.85715 (11) | 0.0139 (3) | |
C5D | 0.98379 (14) | 0.89923 (5) | 0.83297 (10) | 0.0130 (3) | |
H5D | 0.9405 | 0.8749 | 0.7912 | 0.016* | |
C6D | 0.92850 (16) | 0.93953 (6) | 0.77120 (13) | 0.0204 (3) | |
H6D1 | 0.9652 | 0.9650 | 0.8094 | 0.024* | |
H6D2 | 0.9557 | 0.9395 | 0.7150 | 0.024* | |
C7D | 0.77707 (17) | 0.94095 (6) | 0.73724 (13) | 0.0217 (3) | |
H7D1 | 0.7404 | 0.9172 | 0.6931 | 0.026* | |
H7D2 | 0.7455 | 0.9675 | 0.7018 | 0.026* | |
C8D | 0.72720 (16) | 0.93820 (5) | 0.82220 (13) | 0.0195 (3) | |
H8D | 0.7662 | 0.9625 | 0.8653 | 0.023* | |
C9D | 0.77905 (15) | 0.89656 (5) | 0.88201 (11) | 0.0144 (3) | |
C10D | 0.93597 (14) | 0.89666 (5) | 0.92164 (11) | 0.0137 (3) | |
C11D | 0.71819 (15) | 0.89022 (6) | 0.96141 (12) | 0.0181 (3) | |
H11G | 0.7825 | 0.8772 | 1.0191 | 0.022* | |
H11H | 0.6899 | 0.9176 | 0.9793 | 0.022* | |
C12D | 0.59885 (15) | 0.86016 (6) | 0.91604 (12) | 0.0184 (3) | |
H12G | 0.5870 | 0.8413 | 0.9649 | 0.022* | |
H12H | 0.5179 | 0.8766 | 0.8857 | 0.022* | |
C13D | 0.63412 (15) | 0.83426 (5) | 0.84005 (11) | 0.0141 (3) | |
C14D | 0.52079 (15) | 0.82714 (5) | 0.74216 (11) | 0.0158 (3) | |
H14G | 0.4731 | 0.8540 | 0.7223 | 0.019* | |
H14H | 0.5593 | 0.8198 | 0.6938 | 0.019* | |
C15D | 0.42142 (14) | 0.79236 (5) | 0.74190 (11) | 0.0152 (3) | |
C16D | 0.69695 (15) | 0.79137 (5) | 0.88351 (11) | 0.0162 (3) | |
H16G | 0.7663 | 0.7967 | 0.9461 | 0.019* | |
H16H | 0.6297 | 0.7735 | 0.8946 | 0.019* | |
C17D | 0.57610 (17) | 0.94410 (6) | 0.78520 (15) | 0.0261 (4) | |
H17J | 0.5533 | 0.9713 | 0.7526 | 0.031* | |
H17K | 0.5459 | 0.9433 | 0.8392 | 0.031* | |
H17L | 0.5343 | 0.9214 | 0.7406 | 0.031* | |
C18D | 1.16578 (15) | 0.88714 (5) | 0.76254 (11) | 0.0173 (3) | |
H18G | 1.1324 | 0.9123 | 0.7222 | 0.021* | |
H18H | 1.2614 | 0.8863 | 0.7790 | 0.021* | |
C19D | 1.22303 (16) | 0.93066 (6) | 0.90932 (12) | 0.0196 (3) | |
H19J | 1.2231 | 0.9327 | 0.9744 | 0.023* | |
H19K | 1.1876 | 0.9567 | 0.8746 | 0.023* | |
H19L | 1.3124 | 0.9265 | 0.9115 | 0.023* | |
C20D | 0.98343 (16) | 0.93449 (6) | 0.99387 (12) | 0.0209 (3) | |
H20J | 0.9300 | 0.9359 | 1.0339 | 0.025* | |
H20K | 0.9748 | 0.9610 | 0.9584 | 0.025* | |
H20L | 1.0749 | 0.9302 | 1.0342 | 0.025* | |
O1E | 0.44041 (15) | 0.70458 (5) | 0.92456 (10) | 0.0358 (3) | |
N1E | 0.49490 (16) | 0.73948 (5) | 1.06861 (11) | 0.0269 (3) | |
C1E | 0.41253 (18) | 0.72797 (6) | 0.98094 (13) | 0.0265 (4) | |
H1E | 0.3262 | 0.7387 | 0.9608 | 0.032* | |
C2E | 0.6320 (2) | 0.72571 (11) | 1.10321 (17) | 0.0517 (7) | |
H2E1 | 0.6353 | 0.6948 | 1.1020 | 0.062* | |
H2E2 | 0.6761 | 0.7357 | 1.1686 | 0.062* | |
H2E3 | 0.6756 | 0.7373 | 1.0620 | 0.062* | |
C3E | 0.4528 (3) | 0.76764 (8) | 1.13074 (15) | 0.0428 (5) | |
H3E1 | 0.3592 | 0.7733 | 1.1006 | 0.051* | |
H3E2 | 0.5012 | 0.7942 | 1.1403 | 0.051* | |
H3E3 | 0.4698 | 0.7539 | 1.1925 | 0.051* | |
O1F | 1.08805 (15) | 0.73647 (5) | 0.95475 (10) | 0.0375 (3) | |
N1F | 1.06742 (16) | 0.71574 (5) | 1.09615 (11) | 0.0280 (3) | |
C1F | 1.0300 (2) | 0.73634 (7) | 1.01239 (15) | 0.0330 (4) | |
H1F | 0.9519 | 0.7523 | 0.9956 | 0.040* | |
C2F | 0.9897 (2) | 0.71791 (9) | 1.15938 (16) | 0.0414 (5) | |
H2F1 | 0.9155 | 0.7369 | 1.1314 | 0.050* | |
H2F2 | 1.0447 | 0.7285 | 1.2222 | 0.050* | |
H2F3 | 0.9578 | 0.6897 | 1.1663 | 0.050* | |
C3F | 1.1843 (3) | 0.68860 (8) | 1.12828 (16) | 0.0425 (5) | |
H3F1 | 1.1578 | 0.6590 | 1.1261 | 0.051* | |
H3F2 | 1.2387 | 0.6961 | 1.1938 | 0.051* | |
H3F3 | 1.2341 | 0.6927 | 1.0863 | 0.051* | |
O1W | −0.08655 (17) | 0.73237 (7) | 0.36065 (13) | 0.0546 (5) | |
H1W1 | −0.1462 | 0.7130 | 0.3457 | 0.065* | |
H1W2 | −0.0143 | 0.7187 | 0.3714 | 0.065* | |
O2W | −0.10336 (12) | 0.68089 (4) | 0.54947 (9) | 0.0261 (3) | |
H2W1 | −0.1595 | 0.6660 | 0.5052 | 0.031* | |
H2W2 | −0.1338 | 0.6814 | 0.5954 | 0.031* | |
O3W | 0.13813 (14) | 0.76660 (5) | 0.53687 (10) | 0.0320 (3) | |
H3W1 | 0.1593 | 0.7669 | 0.4865 | 0.038* | |
H3W2 | 0.1806 | 0.7876 | 0.5709 | 0.038* | |
O4W | 0.19933 (12) | 0.72242 (4) | 0.75952 (9) | 0.0248 (3) | |
H4W1 | 0.2305 | 0.7475 | 0.7584 | 0.030* | |
H4W2 | 0.2567 | 0.7103 | 0.8084 | 0.030* | |
O5W | 0.34655 (14) | 0.64496 (5) | 0.72072 (11) | 0.0401 (4) | |
H5W1 | 0.4233 | 0.6391 | 0.7617 | 0.048* | |
H5W2 | 0.2946 | 0.6280 | 0.7354 | 0.048* | |
O6W | 0.91141 (12) | 0.78422 (4) | 0.71228 (9) | 0.0274 (3) | |
H6W1 | 0.8353 | 0.7866 | 0.6676 | 0.033* | |
H6W2 | 0.9538 | 0.8064 | 0.7057 | 0.033* | |
O7W | 1.15627 (19) | 0.55177 (5) | 0.14655 (11) | 0.0439 (4) | |
H7W1 | 1.1582 | 0.5705 | 0.1891 | 0.053* | |
H7W2 | 1.1494 | 0.5664 | 0.0961 | 0.053* | |
O8W | −0.50041 (18) | 0.89331 (6) | 0.12057 (12) | 0.0512 (4) | |
H8W1 | −0.5442 | 0.8768 | 0.0740 | 0.061* | |
H8W2 | −0.4552 | 0.8763 | 0.1654 | 0.061* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Na1 | 0.0432 (4) | 0.0265 (4) | 0.0355 (4) | 0.0062 (3) | 0.0208 (3) | 0.0032 (3) |
Na2 | 0.0179 (3) | 0.0179 (3) | 0.0184 (3) | −0.0027 (2) | 0.0081 (2) | −0.0037 (2) |
Na3 | 0.0155 (3) | 0.0171 (3) | 0.0200 (3) | 0.0019 (2) | 0.0063 (2) | −0.0012 (2) |
Na4 | 0.0221 (3) | 0.0230 (4) | 0.0271 (3) | −0.0026 (3) | 0.0085 (3) | 0.0032 (3) |
O1A | 0.0216 (6) | 0.0324 (7) | 0.0225 (6) | −0.0102 (5) | 0.0134 (5) | −0.0088 (5) |
O2A | 0.0212 (6) | 0.0260 (7) | 0.0286 (6) | −0.0065 (5) | 0.0120 (5) | −0.0134 (5) |
O3A | 0.0122 (5) | 0.0123 (5) | 0.0180 (5) | 0.0009 (4) | 0.0032 (4) | −0.0045 (4) |
O4A | 0.0241 (6) | 0.0153 (6) | 0.0408 (7) | 0.0004 (5) | 0.0165 (5) | −0.0027 (5) |
O5A | 0.0202 (5) | 0.0204 (6) | 0.0197 (5) | −0.0007 (4) | 0.0103 (4) | −0.0047 (4) |
O6A | 0.0163 (5) | 0.0153 (6) | 0.0193 (5) | 0.0005 (4) | 0.0051 (4) | −0.0017 (4) |
C1A | 0.0176 (7) | 0.0211 (8) | 0.0141 (7) | −0.0008 (6) | 0.0050 (6) | −0.0014 (6) |
C2A | 0.0211 (8) | 0.0252 (9) | 0.0138 (7) | −0.0026 (6) | 0.0066 (6) | −0.0019 (6) |
C3A | 0.0161 (7) | 0.0207 (8) | 0.0184 (7) | −0.0037 (6) | 0.0093 (6) | −0.0043 (6) |
C4A | 0.0143 (7) | 0.0184 (8) | 0.0170 (7) | −0.0009 (6) | 0.0057 (6) | −0.0037 (6) |
C5A | 0.0125 (6) | 0.0124 (7) | 0.0148 (7) | 0.0001 (5) | 0.0043 (5) | −0.0031 (5) |
C6A | 0.0162 (7) | 0.0208 (8) | 0.0175 (7) | 0.0009 (6) | 0.0042 (6) | 0.0022 (6) |
C7A | 0.0231 (8) | 0.0201 (8) | 0.0168 (7) | 0.0006 (6) | 0.0079 (6) | 0.0029 (6) |
C8A | 0.0192 (7) | 0.0142 (8) | 0.0213 (7) | −0.0002 (6) | 0.0107 (6) | −0.0010 (6) |
C9A | 0.0147 (7) | 0.0110 (7) | 0.0164 (7) | −0.0015 (5) | 0.0062 (6) | −0.0033 (5) |
C10A | 0.0135 (6) | 0.0145 (8) | 0.0137 (7) | −0.0013 (5) | 0.0047 (5) | −0.0034 (5) |
C11A | 0.0140 (7) | 0.0173 (8) | 0.0207 (7) | −0.0031 (6) | 0.0053 (6) | −0.0059 (6) |
C12A | 0.0134 (7) | 0.0200 (8) | 0.0218 (7) | 0.0004 (6) | 0.0053 (6) | −0.0043 (6) |
C13A | 0.0113 (6) | 0.0166 (8) | 0.0181 (7) | 0.0017 (6) | 0.0047 (5) | −0.0019 (6) |
C14A | 0.0169 (7) | 0.0181 (8) | 0.0175 (7) | 0.0031 (6) | 0.0044 (6) | −0.0040 (6) |
C15A | 0.0162 (7) | 0.0100 (7) | 0.0199 (7) | −0.0016 (5) | 0.0087 (6) | 0.0014 (6) |
C16A | 0.0176 (7) | 0.0196 (8) | 0.0209 (8) | 0.0040 (6) | 0.0066 (6) | 0.0010 (6) |
C17A | 0.0254 (8) | 0.0198 (9) | 0.0273 (8) | −0.0002 (6) | 0.0157 (7) | 0.0030 (7) |
C18A | 0.0158 (7) | 0.0236 (9) | 0.0195 (7) | −0.0038 (6) | 0.0059 (6) | −0.0041 (6) |
C19A | 0.0181 (8) | 0.0240 (9) | 0.0280 (8) | 0.0022 (6) | 0.0099 (7) | −0.0024 (7) |
C20A | 0.0176 (7) | 0.0176 (8) | 0.0232 (8) | −0.0017 (6) | 0.0084 (6) | −0.0074 (6) |
O1B | 0.0161 (6) | 0.0401 (8) | 0.0234 (6) | −0.0063 (5) | 0.0022 (5) | 0.0069 (5) |
O2B | 0.0221 (6) | 0.0311 (7) | 0.0198 (6) | −0.0061 (5) | 0.0038 (5) | 0.0052 (5) |
O3B | 0.0196 (5) | 0.0117 (5) | 0.0148 (5) | 0.0036 (4) | 0.0082 (4) | 0.0023 (4) |
O4B | 0.0219 (6) | 0.0144 (6) | 0.0291 (6) | 0.0032 (4) | 0.0100 (5) | 0.0008 (5) |
O5B | 0.0203 (6) | 0.0184 (6) | 0.0230 (6) | 0.0025 (4) | 0.0041 (5) | 0.0043 (5) |
O6B | 0.0293 (6) | 0.0187 (6) | 0.0240 (6) | 0.0057 (5) | 0.0145 (5) | 0.0026 (5) |
C1B | 0.0194 (7) | 0.0243 (9) | 0.0145 (7) | −0.0006 (6) | 0.0058 (6) | −0.0006 (6) |
C2B | 0.0205 (8) | 0.0259 (9) | 0.0151 (7) | −0.0033 (6) | 0.0026 (6) | −0.0003 (6) |
C3B | 0.0137 (7) | 0.0234 (9) | 0.0190 (7) | −0.0022 (6) | 0.0025 (6) | 0.0052 (6) |
C4B | 0.0152 (7) | 0.0213 (9) | 0.0194 (7) | 0.0012 (6) | 0.0058 (6) | 0.0022 (6) |
C5B | 0.0141 (7) | 0.0150 (8) | 0.0149 (7) | 0.0007 (5) | 0.0042 (5) | 0.0014 (6) |
C6B | 0.0200 (8) | 0.0182 (8) | 0.0184 (7) | 0.0023 (6) | 0.0074 (6) | −0.0013 (6) |
C7B | 0.0197 (8) | 0.0149 (8) | 0.0181 (7) | −0.0009 (6) | 0.0033 (6) | −0.0037 (6) |
C8B | 0.0177 (7) | 0.0124 (8) | 0.0224 (8) | 0.0003 (6) | 0.0055 (6) | 0.0010 (6) |
C9B | 0.0178 (7) | 0.0106 (7) | 0.0161 (7) | 0.0014 (5) | 0.0060 (6) | 0.0037 (5) |
C10B | 0.0171 (7) | 0.0156 (8) | 0.0147 (7) | 0.0014 (6) | 0.0058 (6) | 0.0034 (6) |
C11B | 0.0180 (7) | 0.0198 (8) | 0.0195 (7) | 0.0014 (6) | 0.0086 (6) | 0.0060 (6) |
C12B | 0.0198 (7) | 0.0196 (8) | 0.0180 (7) | 0.0032 (6) | 0.0095 (6) | 0.0045 (6) |
C13B | 0.0180 (7) | 0.0159 (8) | 0.0146 (7) | 0.0043 (6) | 0.0072 (6) | 0.0014 (6) |
C14B | 0.0208 (7) | 0.0148 (8) | 0.0150 (7) | 0.0024 (6) | 0.0058 (6) | 0.0011 (6) |
C15B | 0.0202 (7) | 0.0087 (7) | 0.0201 (7) | −0.0002 (6) | 0.0064 (6) | 0.0011 (6) |
C16B | 0.0233 (8) | 0.0175 (8) | 0.0183 (7) | 0.0038 (6) | 0.0074 (6) | −0.0008 (6) |
C17B | 0.0187 (8) | 0.0184 (9) | 0.0314 (9) | −0.0021 (6) | 0.0070 (7) | −0.0018 (7) |
C18B | 0.0178 (8) | 0.0327 (10) | 0.0209 (8) | −0.0018 (7) | 0.0082 (6) | 0.0013 (7) |
C19B | 0.0197 (8) | 0.0285 (10) | 0.0321 (9) | 0.0067 (7) | 0.0079 (7) | 0.0048 (7) |
C20B | 0.0223 (8) | 0.0228 (9) | 0.0227 (8) | 0.0040 (7) | 0.0079 (6) | 0.0093 (7) |
O1C | 0.0141 (5) | 0.0246 (6) | 0.0193 (5) | 0.0040 (4) | 0.0075 (4) | 0.0012 (4) |
O2C | 0.0155 (5) | 0.0235 (6) | 0.0175 (5) | 0.0022 (4) | 0.0050 (4) | 0.0037 (4) |
O3C | 0.0111 (5) | 0.0129 (5) | 0.0160 (5) | −0.0012 (4) | 0.0047 (4) | 0.0019 (4) |
O4C | 0.0211 (6) | 0.0192 (6) | 0.0294 (6) | 0.0057 (5) | 0.0122 (5) | 0.0024 (5) |
O5C | 0.0170 (5) | 0.0185 (6) | 0.0206 (5) | 0.0018 (4) | 0.0084 (4) | 0.0042 (4) |
O6C | 0.0138 (5) | 0.0223 (6) | 0.0284 (6) | 0.0038 (4) | 0.0079 (4) | 0.0068 (5) |
C1C | 0.0119 (6) | 0.0184 (8) | 0.0143 (6) | 0.0005 (5) | 0.0031 (5) | −0.0014 (6) |
C2C | 0.0165 (7) | 0.0212 (8) | 0.0137 (7) | 0.0017 (6) | 0.0053 (6) | −0.0013 (6) |
C3C | 0.0113 (7) | 0.0163 (8) | 0.0145 (7) | 0.0007 (5) | 0.0055 (5) | 0.0008 (5) |
C4C | 0.0126 (6) | 0.0127 (7) | 0.0174 (7) | −0.0020 (5) | 0.0052 (5) | 0.0018 (6) |
C5C | 0.0146 (7) | 0.0114 (7) | 0.0145 (7) | −0.0006 (5) | 0.0053 (5) | −0.0003 (5) |
C6C | 0.0182 (7) | 0.0153 (8) | 0.0271 (8) | −0.0037 (6) | 0.0092 (6) | −0.0060 (6) |
C7C | 0.0233 (8) | 0.0189 (8) | 0.0254 (8) | −0.0015 (6) | 0.0113 (7) | −0.0093 (6) |
C8C | 0.0195 (7) | 0.0119 (8) | 0.0258 (8) | 0.0030 (6) | 0.0112 (6) | 0.0008 (6) |
C9C | 0.0157 (7) | 0.0117 (7) | 0.0147 (7) | 0.0017 (5) | 0.0060 (6) | 0.0031 (5) |
C10C | 0.0133 (7) | 0.0146 (7) | 0.0148 (7) | 0.0017 (5) | 0.0055 (5) | 0.0025 (6) |
C11C | 0.0120 (7) | 0.0217 (8) | 0.0183 (7) | 0.0032 (6) | 0.0042 (6) | 0.0042 (6) |
C12C | 0.0125 (7) | 0.0219 (9) | 0.0196 (7) | 0.0011 (6) | 0.0050 (6) | 0.0009 (6) |
C13C | 0.0119 (7) | 0.0147 (7) | 0.0166 (7) | −0.0017 (5) | 0.0061 (5) | −0.0005 (6) |
C14C | 0.0170 (7) | 0.0165 (8) | 0.0175 (7) | −0.0025 (6) | 0.0088 (6) | −0.0020 (6) |
C15C | 0.0155 (7) | 0.0171 (8) | 0.0174 (7) | 0.0024 (6) | 0.0095 (6) | 0.0000 (6) |
C16C | 0.0162 (7) | 0.0179 (8) | 0.0207 (7) | −0.0029 (6) | 0.0086 (6) | −0.0041 (6) |
C17C | 0.0240 (8) | 0.0169 (8) | 0.0374 (9) | 0.0044 (6) | 0.0177 (7) | −0.0035 (7) |
C18C | 0.0142 (7) | 0.0175 (8) | 0.0177 (7) | −0.0033 (6) | 0.0049 (6) | −0.0009 (6) |
C19C | 0.0209 (8) | 0.0194 (8) | 0.0265 (8) | −0.0017 (6) | 0.0123 (6) | 0.0060 (7) |
C20C | 0.0188 (7) | 0.0213 (9) | 0.0220 (8) | 0.0040 (6) | 0.0079 (6) | 0.0082 (6) |
O1D | 0.0121 (5) | 0.0282 (7) | 0.0202 (5) | 0.0022 (4) | 0.0060 (4) | −0.0016 (5) |
O2D | 0.0174 (5) | 0.0199 (6) | 0.0164 (5) | 0.0004 (4) | 0.0060 (4) | −0.0039 (4) |
O3D | 0.0122 (5) | 0.0119 (5) | 0.0151 (5) | −0.0034 (4) | 0.0059 (4) | −0.0023 (4) |
O4D | 0.0202 (5) | 0.0139 (6) | 0.0277 (6) | −0.0007 (4) | 0.0112 (5) | −0.0006 (4) |
O5D | 0.0187 (5) | 0.0171 (6) | 0.0266 (6) | −0.0025 (4) | 0.0108 (5) | −0.0082 (5) |
O6D | 0.0176 (5) | 0.0190 (6) | 0.0356 (7) | −0.0010 (4) | 0.0146 (5) | −0.0066 (5) |
C1D | 0.0138 (7) | 0.0197 (8) | 0.0156 (7) | −0.0004 (6) | 0.0067 (5) | 0.0018 (6) |
C2D | 0.0146 (7) | 0.0209 (8) | 0.0137 (7) | 0.0000 (6) | 0.0035 (5) | 0.0012 (6) |
C3D | 0.0113 (6) | 0.0165 (8) | 0.0164 (7) | 0.0000 (5) | 0.0044 (5) | −0.0003 (6) |
C4D | 0.0131 (7) | 0.0135 (8) | 0.0154 (7) | −0.0029 (5) | 0.0055 (5) | −0.0011 (5) |
C5D | 0.0137 (7) | 0.0120 (7) | 0.0137 (6) | −0.0013 (5) | 0.0054 (5) | −0.0011 (5) |
C6D | 0.0201 (8) | 0.0170 (8) | 0.0246 (8) | 0.0003 (6) | 0.0086 (6) | 0.0059 (6) |
C7D | 0.0214 (8) | 0.0166 (8) | 0.0265 (8) | 0.0030 (6) | 0.0078 (7) | 0.0080 (6) |
C8D | 0.0176 (7) | 0.0122 (8) | 0.0284 (8) | 0.0018 (6) | 0.0079 (6) | −0.0013 (6) |
C9D | 0.0143 (7) | 0.0119 (7) | 0.0172 (7) | −0.0016 (5) | 0.0060 (5) | −0.0040 (6) |
C10D | 0.0133 (7) | 0.0138 (7) | 0.0148 (7) | −0.0016 (5) | 0.0059 (5) | −0.0039 (6) |
C11D | 0.0150 (7) | 0.0218 (8) | 0.0202 (7) | −0.0021 (6) | 0.0095 (6) | −0.0058 (6) |
C12D | 0.0142 (7) | 0.0231 (9) | 0.0202 (7) | −0.0011 (6) | 0.0090 (6) | −0.0033 (6) |
C13D | 0.0127 (7) | 0.0145 (8) | 0.0163 (7) | −0.0019 (5) | 0.0066 (5) | −0.0008 (5) |
C14D | 0.0150 (7) | 0.0153 (8) | 0.0162 (7) | −0.0007 (6) | 0.0044 (6) | −0.0002 (6) |
C15D | 0.0115 (6) | 0.0165 (8) | 0.0157 (7) | 0.0006 (5) | 0.0025 (5) | −0.0014 (6) |
C16D | 0.0152 (7) | 0.0173 (8) | 0.0166 (7) | −0.0012 (6) | 0.0061 (6) | 0.0022 (6) |
C17D | 0.0188 (8) | 0.0160 (9) | 0.0427 (10) | 0.0051 (6) | 0.0100 (7) | 0.0056 (7) |
C18D | 0.0174 (7) | 0.0189 (8) | 0.0172 (7) | −0.0026 (6) | 0.0083 (6) | −0.0006 (6) |
C19D | 0.0174 (7) | 0.0185 (8) | 0.0228 (8) | −0.0074 (6) | 0.0072 (6) | −0.0056 (6) |
C20D | 0.0168 (7) | 0.0234 (9) | 0.0230 (8) | −0.0045 (6) | 0.0076 (6) | −0.0111 (7) |
O1E | 0.0407 (8) | 0.0422 (9) | 0.0264 (6) | 0.0101 (6) | 0.0142 (6) | −0.0045 (6) |
N1E | 0.0281 (8) | 0.0276 (8) | 0.0239 (7) | 0.0012 (6) | 0.0081 (6) | −0.0020 (6) |
C1E | 0.0261 (8) | 0.0292 (10) | 0.0242 (8) | 0.0043 (7) | 0.0091 (7) | −0.0023 (7) |
C2E | 0.0278 (11) | 0.089 (2) | 0.0347 (11) | 0.0074 (12) | 0.0071 (9) | 0.0059 (12) |
C3E | 0.0579 (14) | 0.0365 (12) | 0.0260 (10) | 0.0148 (10) | 0.0052 (9) | −0.0082 (9) |
O1F | 0.0359 (8) | 0.0482 (9) | 0.0266 (7) | −0.0010 (6) | 0.0088 (6) | 0.0020 (6) |
N1F | 0.0278 (8) | 0.0275 (9) | 0.0252 (7) | 0.0004 (6) | 0.0053 (6) | 0.0018 (6) |
C1F | 0.0268 (9) | 0.0359 (11) | 0.0331 (10) | 0.0022 (8) | 0.0069 (8) | 0.0053 (8) |
C2F | 0.0374 (11) | 0.0540 (15) | 0.0349 (11) | −0.0026 (10) | 0.0155 (9) | 0.0019 (10) |
C3F | 0.0520 (13) | 0.0417 (13) | 0.0321 (10) | 0.0191 (10) | 0.0127 (10) | 0.0090 (9) |
O1W | 0.0367 (8) | 0.0813 (14) | 0.0515 (10) | −0.0099 (8) | 0.0227 (8) | −0.0231 (9) |
O2W | 0.0232 (6) | 0.0317 (7) | 0.0245 (6) | −0.0011 (5) | 0.0101 (5) | −0.0051 (5) |
O3W | 0.0302 (7) | 0.0327 (8) | 0.0349 (7) | 0.0029 (5) | 0.0139 (6) | 0.0048 (6) |
O4W | 0.0226 (6) | 0.0248 (7) | 0.0270 (6) | −0.0040 (5) | 0.0090 (5) | 0.0009 (5) |
O5W | 0.0286 (7) | 0.0390 (9) | 0.0404 (8) | −0.0123 (6) | −0.0029 (6) | 0.0187 (7) |
O6W | 0.0222 (6) | 0.0266 (7) | 0.0301 (6) | −0.0045 (5) | 0.0054 (5) | 0.0081 (5) |
O7W | 0.0746 (12) | 0.0325 (8) | 0.0365 (8) | 0.0038 (7) | 0.0346 (8) | −0.0002 (6) |
O8W | 0.0562 (10) | 0.0363 (9) | 0.0411 (9) | −0.0012 (8) | −0.0071 (8) | −0.0028 (7) |
Geometric parameters (Å, º) top
Na1—O2B | 2.3488 (16) | O3C—C9C | 1.4601 (17) |
Na1—O1W | 2.3917 (18) | O4C—C16C | 1.427 (2) |
Na1—O2W | 2.4151 (16) | O4C—H4OC | 0.8201 |
Na1—O3W | 2.5605 (16) | O5C—C15C | 1.265 (2) |
Na1—O5Bi | 2.6656 (14) | O6C—C15C | 1.2616 (19) |
Na1—O6Bi | 2.9399 (15) | C1C—C2C | 1.531 (2) |
Na1—H1W1 | 2.6504 | C1C—C10C | 1.538 (2) |
Na2—O5A | 2.2860 (12) | C1C—H1C1 | 0.9700 |
Na2—O5W | 2.3124 (16) | C1C—H1C2 | 0.9699 |
Na2—O2Ai | 2.3841 (13) | C2C—C3C | 1.517 (2) |
Na2—O5D | 2.3928 (13) | C2C—H2C1 | 0.9699 |
Na2—O3W | 2.4779 (15) | C2C—H2C2 | 0.9698 |
Na2—O4W | 2.5377 (14) | C3C—C4C | 1.547 (2) |
Na2—H4W1 | 2.6402 | C3C—H3C | 0.9800 |
Na3—O5D | 2.3479 (12) | C4C—C19C | 1.535 (2) |
Na3—O5C | 2.3640 (12) | C4C—C18C | 1.546 (2) |
Na3—O5A | 2.4036 (13) | C4C—C5C | 1.563 (2) |
Na3—O4C | 2.5108 (14) | C5C—C6C | 1.537 (2) |
Na3—O4D | 2.5130 (13) | C5C—C10C | 1.565 (2) |
Na3—O5B | 2.5358 (14) | C5C—H5C | 0.9799 |
Na4—O1F | 2.2610 (16) | C6C—C7C | 1.526 (2) |
Na4—O4Wii | 2.2782 (14) | C6C—H6C1 | 0.9699 |
Na4—O6W | 2.3304 (15) | C6C—H6C2 | 0.9700 |
Na4—O5C | 2.3856 (13) | C7C—C8C | 1.521 (2) |
Na4—O6C | 2.4619 (14) | C7C—H7C1 | 0.9698 |
Na4—C15C | 2.7342 (18) | C7C—H7C2 | 0.9699 |
O1A—C3A | 1.4311 (18) | C8C—C17C | 1.531 (2) |
O1A—H1A | 0.8200 | C8C—C9C | 1.551 (2) |
O2A—C18A | 1.440 (2) | C8C—H8C | 0.9800 |
O2A—Na2ii | 2.3841 (13) | C9C—C11C | 1.540 (2) |
O2A—H2OA | 0.8200 | C9C—C10C | 1.582 (2) |
O3A—C13A | 1.4514 (18) | C10C—C20C | 1.549 (2) |
O3A—C9A | 1.4520 (18) | C11C—C12C | 1.533 (2) |
O4A—C16A | 1.423 (2) | C11C—H11E | 0.9700 |
O4A—H4A | 0.8200 | C11C—H11F | 0.9700 |
O5A—C15A | 1.2518 (19) | C12C—C13C | 1.537 (2) |
O6A—C15A | 1.2633 (19) | C12C—H12E | 0.9700 |
C1A—C2A | 1.532 (2) | C12C—H12F | 0.9700 |
C1A—C10A | 1.535 (2) | C13C—C16C | 1.530 (2) |
C1A—H1A1 | 0.9699 | C13C—C14C | 1.535 (2) |
C1A—H1A2 | 0.9702 | C14C—C15C | 1.520 (2) |
C2A—C3A | 1.509 (2) | C14C—H14E | 0.9699 |
C2A—H2A1 | 0.9700 | C14C—H14F | 0.9699 |
C2A—H2A2 | 0.9699 | C16C—H16E | 0.9698 |
C3A—C4A | 1.539 (2) | C16C—H16F | 0.9701 |
C3A—H3A | 0.9797 | C17C—H17G | 0.9599 |
C4A—C19A | 1.537 (2) | C17C—H17H | 0.9601 |
C4A—C18A | 1.553 (2) | C17C—H17I | 0.9595 |
C4A—C5A | 1.562 (2) | C18C—H18E | 0.9700 |
C5A—C6A | 1.525 (2) | C18C—H18F | 0.9698 |
C5A—C10A | 1.568 (2) | C19C—H19G | 0.9600 |
C5A—H5A | 0.9801 | C19C—H19H | 0.9599 |
C6A—C7A | 1.528 (2) | C19C—H19I | 0.9602 |
C6A—H6A1 | 0.9700 | C20C—H20G | 0.9600 |
C6A—H6A2 | 0.9701 | C20C—H20H | 0.9597 |
C7A—C8A | 1.530 (2) | C20C—H20I | 0.9599 |
C7A—H7A1 | 0.9699 | O1D—C3D | 1.4366 (17) |
C7A—H7A2 | 0.9701 | O1D—H1D | 0.8200 |
C8A—C17A | 1.531 (2) | O2D—C18D | 1.435 (2) |
C8A—C9A | 1.555 (2) | O2D—H2OD | 0.8200 |
C8A—H8A | 0.9799 | O3D—C13D | 1.4493 (17) |
C9A—C11A | 1.540 (2) | O3D—C9D | 1.4573 (18) |
C9A—C10A | 1.580 (2) | O4D—C16D | 1.4175 (19) |
C10A—C20A | 1.542 (2) | O4D—H4OD | 0.8199 |
C11A—C12A | 1.537 (2) | O5D—C15D | 1.244 (2) |
C11A—H11A | 0.9700 | O6D—C15D | 1.2810 (19) |
C11A—H11B | 0.9701 | C1D—C2D | 1.526 (2) |
C12A—C13A | 1.530 (2) | C1D—C10D | 1.544 (2) |
C12A—H12A | 0.9703 | C1D—H1D1 | 0.9701 |
C12A—H12B | 0.9700 | C1D—H1D2 | 0.9699 |
C13A—C14A | 1.521 (2) | C2D—C3D | 1.512 (2) |
C13A—C16A | 1.528 (2) | C2D—H2D1 | 0.9698 |
C14A—C15A | 1.521 (2) | C2D—H2D2 | 0.9703 |
C14A—H14A | 0.9701 | C3D—C4D | 1.546 (2) |
C14A—H14B | 0.9700 | C3D—H3D | 0.9800 |
C16A—H16A | 0.9701 | C4D—C19D | 1.541 (2) |
C16A—H16B | 0.9701 | C4D—C18D | 1.542 (2) |
C17A—H17A | 0.9601 | C4D—C5D | 1.565 (2) |
C17A—H17B | 0.9599 | C5D—C6D | 1.537 (2) |
C17A—H17C | 0.9601 | C5D—C10D | 1.566 (2) |
C18A—H18A | 0.9699 | C5D—H5D | 0.9799 |
C18A—H18B | 0.9699 | C6D—C7D | 1.525 (2) |
C19A—H19A | 0.9601 | C6D—H6D1 | 0.9698 |
C19A—H19B | 0.9602 | C6D—H6D2 | 0.9700 |
C19A—H19C | 0.9600 | C7D—C8D | 1.529 (2) |
C20A—H20A | 0.9600 | C7D—H7D1 | 0.9699 |
C20A—H20B | 0.9600 | C7D—H7D2 | 0.9700 |
C20A—H20C | 0.9600 | C8D—C17D | 1.530 (2) |
O1B—C3B | 1.4399 (19) | C8D—C9D | 1.552 (2) |
O1B—H1B | 0.8200 | C8D—H8D | 0.9795 |
O2B—C18B | 1.423 (2) | C9D—C11D | 1.543 (2) |
O2B—H2OB | 0.8200 | C9D—C10D | 1.577 (2) |
O3B—C9B | 1.4523 (18) | C10D—C20D | 1.544 (2) |
O3B—C13B | 1.4544 (18) | C11D—C12D | 1.534 (2) |
O4B—C16B | 1.428 (2) | C11D—H11G | 0.9699 |
O4B—H4B | 0.8200 | C11D—H11H | 0.9700 |
O5B—C15B | 1.262 (2) | C12D—C13D | 1.532 (2) |
O5B—Na1ii | 2.6656 (14) | C12D—H12G | 0.9702 |
O6B—C15B | 1.267 (2) | C12D—H12H | 0.9699 |
O6B—Na1ii | 2.9399 (15) | C13D—C16D | 1.527 (2) |
C1B—C2B | 1.529 (2) | C13D—C14D | 1.534 (2) |
C1B—C10B | 1.539 (2) | C14D—C15D | 1.519 (2) |
C1B—H1B1 | 0.9700 | C14D—H14G | 0.9698 |
C1B—H1B2 | 0.9696 | C14D—H14H | 0.9701 |
C2B—C3B | 1.515 (2) | C16D—H16G | 0.9700 |
C2B—H2B1 | 0.9700 | C16D—H16H | 0.9701 |
C2B—H2B2 | 0.9700 | C17D—H17J | 0.9596 |
C3B—C4B | 1.536 (2) | C17D—H17K | 0.9600 |
C3B—H3B | 0.9800 | C17D—H17L | 0.9599 |
C4B—C18B | 1.539 (2) | C18D—H18G | 0.9699 |
C4B—C19B | 1.542 (2) | C18D—H18H | 0.9700 |
C4B—C5B | 1.568 (2) | C19D—H19J | 0.9600 |
C5B—C6B | 1.530 (2) | C19D—H19K | 0.9601 |
C5B—C10B | 1.563 (2) | C19D—H19L | 0.9601 |
C5B—H5B | 0.9800 | C20D—H20J | 0.9599 |
C6B—C7B | 1.526 (2) | C20D—H20K | 0.9607 |
C6B—H6B1 | 0.9700 | C20D—H20L | 0.9600 |
C6B—H6B2 | 0.9700 | O1E—C1E | 1.218 (2) |
C7B—C8B | 1.525 (2) | N1E—C1E | 1.327 (2) |
C7B—H7B1 | 0.9702 | N1E—C2E | 1.443 (3) |
C7B—H7B2 | 0.9702 | N1E—C3E | 1.450 (3) |
C8B—C17B | 1.532 (2) | C1E—H1E | 0.9300 |
C8B—C9B | 1.553 (2) | C2E—H2E1 | 0.9599 |
C8B—H8B | 0.9800 | C2E—H2E2 | 0.9599 |
C9B—C11B | 1.539 (2) | C2E—H2E3 | 0.9599 |
C9B—C10B | 1.586 (2) | C3E—H3E1 | 0.9599 |
C10B—C20B | 1.545 (2) | C3E—H3E2 | 0.9600 |
C11B—C12B | 1.533 (2) | C3E—H3E3 | 0.9600 |
C11B—H11C | 0.9700 | O1F—C1F | 1.220 (3) |
C11B—H11D | 0.9701 | N1F—C1F | 1.318 (3) |
C12B—C13B | 1.534 (2) | N1F—C3F | 1.446 (3) |
C12B—H12C | 0.9699 | N1F—C2F | 1.458 (3) |
C12B—H12D | 0.9699 | C1F—H1F | 0.9300 |
C13B—C16B | 1.524 (2) | C2F—H2F1 | 0.9601 |
C13B—C14B | 1.531 (2) | C2F—H2F2 | 0.9600 |
C14B—C15B | 1.531 (2) | C2F—H2F3 | 0.9601 |
C14B—H14C | 0.9699 | C3F—H3F1 | 0.9600 |
C14B—H14D | 0.9700 | C3F—H3F2 | 0.9602 |
C16B—H16C | 0.9701 | C3F—H3F3 | 0.9598 |
C16B—H16D | 0.9697 | O1W—H1W1 | 0.8500 |
C17B—H17D | 0.9600 | O1W—H1W2 | 0.8498 |
C17B—H17E | 0.9600 | O2W—H2W1 | 0.8501 |
C17B—H17F | 0.9601 | O2W—H2W2 | 0.8493 |
C18B—H18C | 0.9701 | O3W—H3W1 | 0.8499 |
C18B—H18D | 0.9699 | O3W—H3W2 | 0.8500 |
C19B—H19D | 0.9600 | O4W—Na4i | 2.2782 (14) |
C19B—H19E | 0.9600 | O4W—H4W1 | 0.8501 |
C19B—H19F | 0.9600 | O4W—H4W2 | 0.8499 |
C20B—H20D | 0.9600 | O5W—H5W1 | 0.8500 |
C20B—H20E | 0.9600 | O5W—H5W2 | 0.8500 |
C20B—H20F | 0.9600 | O6W—H6W1 | 0.8500 |
O1C—C3C | 1.4324 (17) | O6W—H6W2 | 0.8498 |
O1C—H1C | 0.8200 | O7W—H7W1 | 0.8501 |
O2C—C18C | 1.433 (2) | O7W—H7W2 | 0.8501 |
O2C—H2OC | 0.8198 | O8W—H8W1 | 0.8499 |
O3C—C13C | 1.4434 (17) | O8W—H8W2 | 0.8499 |
| | | |
O2B—Na1—O1W | 116.29 (7) | O4B—C16B—C13B | 112.62 (13) |
O2B—Na1—O2W | 157.25 (5) | O4B—C16B—H16C | 109.0 |
O1W—Na1—O2W | 85.61 (7) | C13B—C16B—H16C | 109.1 |
O2B—Na1—O3W | 82.25 (5) | O4B—C16B—H16D | 109.2 |
O1W—Na1—O3W | 75.54 (6) | C13B—C16B—H16D | 109.1 |
O2W—Na1—O3W | 98.53 (5) | H16C—C16B—H16D | 107.8 |
O2B—Na1—O5Bi | 82.13 (5) | C8B—C17B—H17D | 109.5 |
O1W—Na1—O5Bi | 131.15 (6) | C8B—C17B—H17E | 109.5 |
O2W—Na1—O5Bi | 87.80 (5) | H17D—C17B—H17E | 109.5 |
O3W—Na1—O5Bi | 153.17 (6) | C8B—C17B—H17F | 109.4 |
O2B—Na1—O6Bi | 83.48 (5) | H17D—C17B—H17F | 109.5 |
O1W—Na1—O6Bi | 88.81 (6) | H17E—C17B—H17F | 109.5 |
O2W—Na1—O6Bi | 104.17 (5) | O2B—C18B—C4B | 113.87 (14) |
O3W—Na1—O6Bi | 151.30 (5) | O2B—C18B—H18C | 108.7 |
O5Bi—Na1—O6Bi | 46.47 (4) | C4B—C18B—H18C | 108.8 |
O2B—Na1—Na4i | 96.53 (4) | O2B—C18B—H18D | 108.8 |
O1W—Na1—Na4i | 139.39 (6) | C4B—C18B—H18D | 108.8 |
O2W—Na1—Na4i | 60.95 (3) | H18C—C18B—H18D | 107.7 |
O3W—Na1—Na4i | 86.69 (4) | C4B—C19B—H19D | 109.5 |
O5Bi—Na1—Na4i | 73.60 (3) | C4B—C19B—H19E | 109.5 |
O6Bi—Na1—Na4i | 119.66 (3) | H19D—C19B—H19E | 109.5 |
O2B—Na1—Na2 | 110.02 (4) | C4B—C19B—H19F | 109.4 |
O1W—Na1—Na2 | 79.94 (5) | H19D—C19B—H19F | 109.5 |
O2W—Na1—Na2 | 65.73 (4) | H19E—C19B—H19F | 109.5 |
O3W—Na1—Na2 | 33.38 (4) | C10B—C20B—H20D | 109.5 |
O5Bi—Na1—Na2 | 138.80 (4) | C10B—C20B—H20E | 109.5 |
O6Bi—Na1—Na2 | 165.25 (4) | H20D—C20B—H20E | 109.5 |
Na4i—Na1—Na2 | 66.112 (18) | C10B—C20B—H20F | 109.5 |
O2B—Na1—H1W1 | 129.3 | H20D—C20B—H20F | 109.5 |
O1W—Na1—H1W1 | 18.5 | H20E—C20B—H20F | 109.5 |
O2W—Na1—H1W1 | 73.4 | C3C—O1C—H1C | 109.5 |
O3W—Na1—H1W1 | 91.3 | C18C—O2C—H2OC | 104.0 |
O5Bi—Na1—H1W1 | 115.4 | C13C—O3C—C9C | 113.01 (11) |
O6Bi—Na1—H1W1 | 78.8 | C16C—O4C—Na3 | 127.68 (9) |
Na4i—Na1—H1W1 | 133.4 | C16C—O4C—H4OC | 110.0 |
Na2—Na1—H1W1 | 87.8 | Na3—O4C—H4OC | 113.5 |
O5A—Na2—O5W | 94.70 (6) | C15C—O5C—Na3 | 125.87 (9) |
O5A—Na2—O2Ai | 93.46 (5) | C15C—O5C—Na4 | 91.75 (9) |
O5W—Na2—O2Ai | 83.27 (6) | Na3—O5C—Na4 | 114.05 (5) |
O5A—Na2—O5D | 79.69 (4) | C15C—O6C—Na4 | 88.37 (10) |
O5W—Na2—O5D | 100.23 (5) | C2C—C1C—C10C | 113.15 (13) |
O2Ai—Na2—O5D | 172.50 (5) | C2C—C1C—H1C1 | 108.9 |
O5A—Na2—O3W | 104.75 (5) | C10C—C1C—H1C1 | 108.9 |
O5W—Na2—O3W | 160.54 (6) | C2C—C1C—H1C2 | 109.0 |
O2Ai—Na2—O3W | 94.69 (5) | C10C—C1C—H1C2 | 109.0 |
O5D—Na2—O3W | 84.20 (5) | H1C1—C1C—H1C2 | 107.8 |
O5A—Na2—O4W | 153.17 (5) | C3C—C2C—C1C | 109.57 (12) |
O5W—Na2—O4W | 77.64 (6) | C3C—C2C—H2C1 | 109.8 |
O2Ai—Na2—O4W | 110.82 (5) | C1C—C2C—H2C1 | 109.8 |
O5D—Na2—O4W | 76.52 (4) | C3C—C2C—H2C2 | 109.7 |
O3W—Na2—O4W | 85.10 (5) | C1C—C2C—H2C2 | 109.7 |
O5A—Na2—Na3 | 43.39 (3) | H2C1—C2C—H2C2 | 108.2 |
O5W—Na2—Na3 | 82.63 (4) | O1C—C3C—C2C | 108.06 (12) |
O2Ai—Na2—Na3 | 132.68 (4) | O1C—C3C—C4C | 111.59 (12) |
O5D—Na2—Na3 | 42.26 (3) | C2C—C3C—C4C | 113.34 (12) |
O3W—Na2—Na3 | 112.03 (4) | O1C—C3C—H3C | 107.9 |
O4W—Na2—Na3 | 109.79 (4) | C2C—C3C—H3C | 107.9 |
O5A—Na2—Na1 | 130.03 (4) | C4C—C3C—H3C | 107.9 |
O5W—Na2—Na1 | 128.47 (4) | C19C—C4C—C18C | 105.07 (12) |
O2Ai—Na2—Na1 | 71.50 (4) | C19C—C4C—C3C | 111.72 (13) |
O5D—Na2—Na1 | 110.57 (4) | C18C—C4C—C3C | 106.91 (12) |
O3W—Na2—Na1 | 34.64 (4) | C19C—C4C—C5C | 113.77 (13) |
O4W—Na2—Na1 | 71.04 (3) | C18C—C4C—C5C | 109.78 (12) |
Na3—Na2—Na1 | 146.23 (2) | C3C—C4C—C5C | 109.30 (12) |
O5A—Na2—H4W1 | 140.2 | C6C—C5C—C4C | 113.34 (12) |
O5W—Na2—H4W1 | 90.9 | C6C—C5C—C10C | 111.45 (13) |
O2Ai—Na2—H4W1 | 126.3 | C4C—C5C—C10C | 115.86 (12) |
O5D—Na2—H4W1 | 60.6 | C6C—C5C—H5C | 105.0 |
O3W—Na2—H4W1 | 74.7 | C4C—C5C—H5C | 105.0 |
O4W—Na2—H4W1 | 18.8 | C10C—C5C—H5C | 105.0 |
Na3—Na2—H4W1 | 98.9 | C7C—C6C—C5C | 110.77 (13) |
Na1—Na2—H4W1 | 71.3 | C7C—C6C—H6C1 | 109.6 |
O5D—Na3—O5C | 164.27 (5) | C5C—C6C—H6C1 | 109.5 |
O5D—Na3—O5A | 78.26 (4) | C7C—C6C—H6C2 | 109.4 |
O5C—Na3—O5A | 111.68 (5) | C5C—C6C—H6C2 | 109.4 |
O5D—Na3—O4C | 80.55 (4) | H6C1—C6C—H6C2 | 108.0 |
O5C—Na3—O4C | 85.01 (4) | C8C—C7C—C6C | 111.83 (14) |
O5A—Na3—O4C | 104.64 (5) | C8C—C7C—H7C1 | 109.2 |
O5D—Na3—O4D | 84.89 (4) | C6C—C7C—H7C1 | 109.1 |
O5C—Na3—O4D | 86.28 (4) | C8C—C7C—H7C2 | 109.3 |
O5A—Na3—O4D | 161.79 (5) | C6C—C7C—H7C2 | 109.4 |
O4C—Na3—O4D | 79.06 (4) | H7C1—C7C—H7C2 | 107.9 |
O5D—Na3—O5B | 109.59 (5) | C7C—C8C—C17C | 109.93 (14) |
O5C—Na3—O5B | 83.96 (4) | C7C—C8C—C9C | 110.62 (13) |
O5A—Na3—O5B | 85.54 (4) | C17C—C8C—C9C | 115.03 (14) |
O4C—Na3—O5B | 167.18 (5) | C7C—C8C—H8C | 106.9 |
O4D—Na3—O5B | 93.72 (4) | C17C—C8C—H8C | 106.9 |
O5D—Na3—Na2 | 43.26 (3) | C9C—C8C—H8C | 106.9 |
O5C—Na3—Na2 | 138.77 (4) | O3C—C9C—C11C | 104.39 (12) |
O5A—Na3—Na2 | 40.80 (3) | O3C—C9C—C8C | 109.05 (12) |
O4C—Na3—Na2 | 77.93 (3) | C11C—C9C—C8C | 111.91 (13) |
O4D—Na3—Na2 | 125.79 (3) | O3C—C9C—C10C | 108.12 (11) |
O5B—Na3—Na2 | 114.79 (3) | C11C—C9C—C10C | 113.49 (12) |
O5D—Na3—Na4 | 140.32 (4) | C8C—C9C—C10C | 109.61 (12) |
O5C—Na3—Na4 | 33.14 (3) | C1C—C10C—C20C | 108.96 (13) |
O5A—Na3—Na4 | 141.00 (4) | C1C—C10C—C5C | 107.62 (12) |
O4C—Na3—Na4 | 90.79 (3) | C20C—C10C—C5C | 113.87 (13) |
O4D—Na3—Na4 | 55.42 (3) | C1C—C10C—C9C | 110.60 (12) |
O5B—Na3—Na4 | 76.40 (3) | C20C—C10C—C9C | 107.60 (12) |
Na2—Na3—Na4 | 167.64 (2) | C5C—C10C—C9C | 108.20 (11) |
O1F—Na4—O4Wii | 101.38 (6) | C12C—C11C—C9C | 105.59 (12) |
O1F—Na4—O6W | 107.39 (6) | C12C—C11C—H11E | 110.6 |
O4Wii—Na4—O6W | 98.72 (5) | C9C—C11C—H11E | 110.6 |
O1F—Na4—O5C | 126.57 (6) | C12C—C11C—H11F | 110.6 |
O4Wii—Na4—O5C | 126.42 (5) | C9C—C11C—H11F | 110.6 |
O6W—Na4—O5C | 89.20 (5) | H11E—C11C—H11F | 108.8 |
O1F—Na4—O6C | 96.06 (6) | C11C—C12C—C13C | 104.37 (12) |
O4Wii—Na4—O6C | 103.66 (5) | C11C—C12C—H12E | 110.9 |
O6W—Na4—O6C | 143.52 (5) | C13C—C12C—H12E | 110.9 |
O5C—Na4—O6C | 54.33 (4) | C11C—C12C—H12F | 110.9 |
O1F—Na4—C15C | 109.49 (6) | C13C—C12C—H12F | 110.9 |
O4Wii—Na4—C15C | 121.81 (5) | H12E—C12C—H12F | 108.9 |
O6W—Na4—C15C | 116.27 (5) | O3C—C13C—C16C | 109.49 (12) |
O5C—Na4—C15C | 27.55 (4) | O3C—C13C—C14C | 106.17 (12) |
O6C—Na4—C15C | 27.47 (4) | C16C—C13C—C14C | 109.72 (13) |
O1F—Na4—Na3 | 111.73 (5) | O3C—C13C—C12C | 106.04 (12) |
O4Wii—Na4—Na3 | 145.87 (4) | C16C—C13C—C12C | 109.70 (13) |
O6W—Na4—Na3 | 64.23 (4) | C14C—C13C—C12C | 115.50 (13) |
O5C—Na4—Na3 | 32.81 (3) | C15C—C14C—C13C | 114.48 (13) |
O6C—Na4—Na3 | 81.42 (3) | C15C—C14C—H14E | 108.6 |
C15C—Na4—Na3 | 54.48 (4) | C13C—C14C—H14E | 108.6 |
O1F—Na4—Na1ii | 152.55 (5) | C15C—C14C—H14F | 108.6 |
O4Wii—Na4—Na1ii | 75.09 (4) | C13C—C14C—H14F | 108.6 |
O6W—Na4—Na1ii | 48.03 (4) | H14E—C14C—H14F | 107.6 |
O5C—Na4—Na1ii | 71.82 (3) | O6C—C15C—O5C | 122.38 (14) |
O6C—Na4—Na1ii | 111.30 (4) | O6C—C15C—C14C | 119.35 (14) |
C15C—Na4—Na1ii | 94.72 (4) | O5C—C15C—C14C | 118.27 (13) |
C3A—O1A—H1A | 109.5 | O6C—C15C—Na4 | 64.17 (9) |
C18A—O2A—Na2ii | 121.82 (10) | O5C—C15C—Na4 | 60.70 (8) |
C18A—O2A—H2OA | 108.3 | C14C—C15C—Na4 | 163.80 (10) |
Na2ii—O2A—H2OA | 107.0 | O4C—C16C—C13C | 110.55 (13) |
C13A—O3A—C9A | 113.10 (11) | O4C—C16C—H16E | 109.6 |
C16A—O4A—H4A | 109.5 | C13C—C16C—H16E | 109.5 |
C15A—O5A—Na2 | 133.08 (10) | O4C—C16C—H16F | 109.5 |
C15A—O5A—Na3 | 130.01 (10) | C13C—C16C—H16F | 109.5 |
Na2—O5A—Na3 | 95.81 (4) | H16E—C16C—H16F | 108.1 |
C2A—C1A—C10A | 112.65 (13) | C8C—C17C—H17G | 109.5 |
C2A—C1A—H1A1 | 109.0 | C8C—C17C—H17H | 109.4 |
C10A—C1A—H1A1 | 109.1 | H17G—C17C—H17H | 109.5 |
C2A—C1A—H1A2 | 109.0 | C8C—C17C—H17I | 109.6 |
C10A—C1A—H1A2 | 109.1 | H17G—C17C—H17I | 109.4 |
H1A1—C1A—H1A2 | 107.8 | H17H—C17C—H17I | 109.5 |
C3A—C2A—C1A | 110.37 (13) | O2C—C18C—C4C | 114.07 (12) |
C3A—C2A—H2A1 | 109.5 | O2C—C18C—H18E | 108.7 |
C1A—C2A—H2A1 | 109.6 | C4C—C18C—H18E | 108.7 |
C3A—C2A—H2A2 | 109.6 | O2C—C18C—H18F | 108.8 |
C1A—C2A—H2A2 | 109.6 | C4C—C18C—H18F | 108.8 |
H2A1—C2A—H2A2 | 108.1 | H18E—C18C—H18F | 107.6 |
O1A—C3A—C2A | 107.55 (12) | C4C—C19C—H19G | 109.5 |
O1A—C3A—C4A | 112.45 (13) | C4C—C19C—H19H | 109.5 |
C2A—C3A—C4A | 112.87 (13) | H19G—C19C—H19H | 109.5 |
O1A—C3A—H3A | 107.9 | C4C—C19C—H19I | 109.5 |
C2A—C3A—H3A | 107.9 | H19G—C19C—H19I | 109.5 |
C4A—C3A—H3A | 107.9 | H19H—C19C—H19I | 109.5 |
C19A—C4A—C3A | 111.45 (13) | C10C—C20C—H20G | 109.5 |
C19A—C4A—C18A | 106.46 (13) | C10C—C20C—H20H | 109.5 |
C3A—C4A—C18A | 107.13 (13) | H20G—C20C—H20H | 109.5 |
C19A—C4A—C5A | 113.20 (13) | C10C—C20C—H20I | 109.4 |
C3A—C4A—C5A | 110.16 (12) | H20G—C20C—H20I | 109.5 |
C18A—C4A—C5A | 108.14 (12) | H20H—C20C—H20I | 109.5 |
C6A—C5A—C4A | 113.29 (12) | C3D—O1D—H1D | 109.5 |
C6A—C5A—C10A | 111.08 (12) | C18D—O2D—H2OD | 107.3 |
C4A—C5A—C10A | 117.47 (12) | C13D—O3D—C9D | 112.96 (11) |
C6A—C5A—H5A | 104.5 | C16D—O4D—Na3 | 122.05 (9) |
C4A—C5A—H5A | 104.5 | C16D—O4D—H4OD | 108.7 |
C10A—C5A—H5A | 104.5 | Na3—O4D—H4OD | 111.2 |
C5A—C6A—C7A | 110.49 (13) | C15D—O5D—Na3 | 131.29 (10) |
C5A—C6A—H6A1 | 110.2 | C15D—O5D—Na2 | 133.64 (10) |
C7A—C6A—H6A1 | 110.2 | Na3—O5D—Na2 | 94.48 (5) |
C5A—C6A—H6A2 | 111.1 | C2D—C1D—C10D | 113.46 (13) |
C7A—C6A—H6A2 | 111.1 | C2D—C1D—H1D1 | 108.9 |
H6A1—C6A—H6A2 | 103.6 | C10D—C1D—H1D1 | 108.9 |
C6A—C7A—C8A | 112.40 (13) | C2D—C1D—H1D2 | 108.9 |
C6A—C7A—H7A1 | 109.1 | C10D—C1D—H1D2 | 108.9 |
C8A—C7A—H7A1 | 109.1 | H1D1—C1D—H1D2 | 107.7 |
C6A—C7A—H7A2 | 109.1 | C3D—C2D—C1D | 110.22 (12) |
C8A—C7A—H7A2 | 109.1 | C3D—C2D—H2D1 | 109.6 |
H7A1—C7A—H7A2 | 107.9 | C1D—C2D—H2D1 | 109.6 |
C7A—C8A—C17A | 109.48 (13) | C3D—C2D—H2D2 | 109.6 |
C7A—C8A—C9A | 110.53 (13) | C1D—C2D—H2D2 | 109.6 |
C17A—C8A—C9A | 116.18 (13) | H2D1—C2D—H2D2 | 108.1 |
C7A—C8A—H8A | 106.7 | O1D—C3D—C2D | 108.32 (12) |
C17A—C8A—H8A | 106.7 | O1D—C3D—C4D | 112.24 (12) |
C9A—C8A—H8A | 106.7 | C2D—C3D—C4D | 112.48 (13) |
O3A—C9A—C11A | 104.20 (12) | O1D—C3D—H3D | 107.9 |
O3A—C9A—C8A | 109.39 (12) | C2D—C3D—H3D | 107.9 |
C11A—C9A—C8A | 111.52 (12) | C4D—C3D—H3D | 107.9 |
O3A—C9A—C10A | 107.31 (11) | C19D—C4D—C18D | 104.22 (12) |
C11A—C9A—C10A | 114.57 (12) | C19D—C4D—C3D | 111.32 (12) |
C8A—C9A—C10A | 109.54 (12) | C18D—C4D—C3D | 108.03 (12) |
C1A—C10A—C20A | 108.06 (12) | C19D—C4D—C5D | 113.86 (13) |
C1A—C10A—C5A | 108.33 (12) | C18D—C4D—C5D | 110.26 (12) |
C20A—C10A—C5A | 114.56 (13) | C3D—C4D—C5D | 108.93 (12) |
C1A—C10A—C9A | 110.55 (12) | C6D—C5D—C4D | 113.61 (12) |
C20A—C10A—C9A | 109.13 (12) | C6D—C5D—C10D | 111.17 (12) |
C5A—C10A—C9A | 106.20 (11) | C4D—C5D—C10D | 115.70 (12) |
C12A—C11A—C9A | 105.19 (12) | C6D—C5D—H5D | 105.0 |
C12A—C11A—H11A | 110.7 | C4D—C5D—H5D | 105.1 |
C9A—C11A—H11A | 110.7 | C10D—C5D—H5D | 105.0 |
C12A—C11A—H11B | 110.7 | C7D—C6D—C5D | 111.09 (13) |
C9A—C11A—H11B | 110.7 | C7D—C6D—H6D1 | 109.4 |
H11A—C11A—H11B | 108.8 | C5D—C6D—H6D1 | 109.4 |
C13A—C12A—C11A | 103.93 (12) | C7D—C6D—H6D2 | 109.5 |
C13A—C12A—H12A | 110.9 | C5D—C6D—H6D2 | 109.5 |
C11A—C12A—H12A | 111.1 | H6D1—C6D—H6D2 | 108.0 |
C13A—C12A—H12B | 110.9 | C6D—C7D—C8D | 112.15 (14) |
C11A—C12A—H12B | 110.9 | C6D—C7D—H7D1 | 109.2 |
H12A—C12A—H12B | 109.0 | C8D—C7D—H7D1 | 109.1 |
O3A—C13A—C14A | 104.02 (12) | C6D—C7D—H7D2 | 109.2 |
O3A—C13A—C16A | 109.50 (12) | C8D—C7D—H7D2 | 109.2 |
C14A—C13A—C16A | 111.72 (14) | H7D1—C7D—H7D2 | 107.9 |
O3A—C13A—C12A | 105.54 (12) | C7D—C8D—C17D | 109.96 (14) |
C14A—C13A—C12A | 116.73 (13) | C7D—C8D—C9D | 110.50 (13) |
C16A—C13A—C12A | 108.88 (13) | C17D—C8D—C9D | 115.00 (14) |
C15A—C14A—C13A | 119.75 (13) | C7D—C8D—H8D | 107.0 |
C15A—C14A—H14A | 107.4 | C17D—C8D—H8D | 107.0 |
C13A—C14A—H14A | 107.4 | C9D—C8D—H8D | 107.0 |
C15A—C14A—H14B | 107.4 | O3D—C9D—C11D | 104.50 (12) |
C13A—C14A—H14B | 107.3 | O3D—C9D—C8D | 108.72 (12) |
H14A—C14A—H14B | 106.9 | C11D—C9D—C8D | 111.83 (13) |
O5A—C15A—O6A | 124.99 (14) | O3D—C9D—C10D | 108.22 (11) |
O5A—C15A—C14A | 115.33 (13) | C11D—C9D—C10D | 114.12 (12) |
O6A—C15A—C14A | 119.68 (13) | C8D—C9D—C10D | 109.17 (12) |
O4A—C16A—C13A | 112.94 (13) | C1D—C10D—C20D | 108.00 (13) |
O4A—C16A—H16A | 109.1 | C1D—C10D—C5D | 107.86 (12) |
C13A—C16A—H16A | 109.1 | C20D—C10D—C5D | 114.09 (13) |
O4A—C16A—H16B | 108.9 | C1D—C10D—C9D | 110.64 (12) |
C13A—C16A—H16B | 108.9 | C20D—C10D—C9D | 107.63 (12) |
H16A—C16A—H16B | 107.8 | C5D—C10D—C9D | 108.62 (11) |
C8A—C17A—H17A | 109.4 | C12D—C11D—C9D | 105.32 (12) |
C8A—C17A—H17B | 109.5 | C12D—C11D—H11G | 110.6 |
H17A—C17A—H17B | 109.5 | C9D—C11D—H11G | 110.6 |
C8A—C17A—H17C | 109.5 | C12D—C11D—H11H | 110.8 |
H17A—C17A—H17C | 109.5 | C9D—C11D—H11H | 110.7 |
H17B—C17A—H17C | 109.4 | H11G—C11D—H11H | 108.8 |
O2A—C18A—C4A | 113.99 (13) | C13D—C12D—C11D | 104.48 (12) |
O2A—C18A—H18A | 108.8 | C13D—C12D—H12G | 110.8 |
C4A—C18A—H18A | 108.8 | C11D—C12D—H12G | 110.9 |
O2A—C18A—H18B | 108.7 | C13D—C12D—H12H | 110.9 |
C4A—C18A—H18B | 108.7 | C11D—C12D—H12H | 110.8 |
H18A—C18A—H18B | 107.6 | H12G—C12D—H12H | 108.9 |
C4A—C19A—H19A | 109.5 | O3D—C13D—C16D | 108.43 (12) |
C4A—C19A—H19B | 109.5 | O3D—C13D—C12D | 105.80 (12) |
H19A—C19A—H19B | 109.4 | C16D—C13D—C12D | 109.94 (13) |
C4A—C19A—H19C | 109.5 | O3D—C13D—C14D | 105.55 (11) |
H19A—C19A—H19C | 109.5 | C16D—C13D—C14D | 110.59 (13) |
H19B—C19A—H19C | 109.5 | C12D—C13D—C14D | 116.08 (13) |
C10A—C20A—H20A | 109.5 | C15D—C14D—C13D | 115.30 (13) |
C10A—C20A—H20B | 109.4 | C15D—C14D—H14G | 108.4 |
H20A—C20A—H20B | 109.5 | C13D—C14D—H14G | 108.4 |
C10A—C20A—H20C | 109.5 | C15D—C14D—H14H | 108.5 |
H20A—C20A—H20C | 109.5 | C13D—C14D—H14H | 108.5 |
H20B—C20A—H20C | 109.5 | H14G—C14D—H14H | 107.5 |
C3B—O1B—H1B | 109.5 | O5D—C15D—O6D | 123.45 (14) |
C18B—O2B—Na1 | 133.96 (11) | O5D—C15D—C14D | 118.19 (13) |
C18B—O2B—H2OB | 110.1 | O6D—C15D—C14D | 118.36 (14) |
Na1—O2B—H2OB | 113.8 | O4D—C16D—C13D | 113.30 (12) |
C9B—O3B—C13B | 112.84 (11) | O4D—C16D—H16G | 108.9 |
C16B—O4B—H4B | 109.5 | C13D—C16D—H16G | 108.9 |
C15B—O5B—Na3 | 122.63 (10) | O4D—C16D—H16H | 109.0 |
C15B—O5B—Na1ii | 100.36 (10) | C13D—C16D—H16H | 108.9 |
Na3—O5B—Na1ii | 130.33 (5) | H16G—C16D—H16H | 107.7 |
C15B—O6B—Na1ii | 87.37 (10) | C8D—C17D—H17J | 109.4 |
C2B—C1B—C10B | 113.17 (14) | C8D—C17D—H17K | 109.5 |
C2B—C1B—H1B1 | 109.0 | H17J—C17D—H17K | 109.5 |
C10B—C1B—H1B1 | 109.0 | C8D—C17D—H17L | 109.5 |
C2B—C1B—H1B2 | 108.9 | H17J—C17D—H17L | 109.5 |
C10B—C1B—H1B2 | 108.9 | H17K—C17D—H17L | 109.5 |
H1B1—C1B—H1B2 | 107.8 | O2D—C18D—C4D | 114.52 (12) |
C3B—C2B—C1B | 110.59 (13) | O2D—C18D—H18G | 108.6 |
C3B—C2B—H2B1 | 109.5 | C4D—C18D—H18G | 108.6 |
C1B—C2B—H2B1 | 109.5 | O2D—C18D—H18H | 108.7 |
C3B—C2B—H2B2 | 109.6 | C4D—C18D—H18H | 108.6 |
C1B—C2B—H2B2 | 109.5 | H18G—C18D—H18H | 107.6 |
H2B1—C2B—H2B2 | 108.1 | C4D—C19D—H19J | 109.4 |
O1B—C3B—C2B | 107.93 (13) | C4D—C19D—H19K | 109.5 |
O1B—C3B—C4B | 111.81 (14) | H19J—C19D—H19K | 109.5 |
C2B—C3B—C4B | 112.81 (13) | C4D—C19D—H19L | 109.5 |
O1B—C3B—H3B | 108.0 | H19J—C19D—H19L | 109.5 |
C2B—C3B—H3B | 108.0 | H19K—C19D—H19L | 109.5 |
C4B—C3B—H3B | 108.0 | C10D—C20D—H20J | 109.5 |
C3B—C4B—C18B | 108.23 (14) | C10D—C20D—H20K | 109.5 |
C3B—C4B—C19B | 111.42 (14) | H20J—C20D—H20K | 109.5 |
C18B—C4B—C19B | 104.63 (14) | C10D—C20D—H20L | 109.5 |
C3B—C4B—C5B | 108.06 (13) | H20J—C20D—H20L | 109.5 |
C18B—C4B—C5B | 109.39 (13) | H20K—C20D—H20L | 109.5 |
C19B—C4B—C5B | 114.89 (14) | C1E—N1E—C2E | 120.43 (18) |
C6B—C5B—C10B | 111.71 (13) | C1E—N1E—C3E | 121.65 (17) |
C6B—C5B—C4B | 113.11 (13) | C2E—N1E—C3E | 117.86 (18) |
C10B—C5B—C4B | 115.88 (12) | O1E—C1E—N1E | 125.55 (18) |
C6B—C5B—H5B | 104.9 | O1E—C1E—H1E | 117.2 |
C10B—C5B—H5B | 105.0 | N1E—C1E—H1E | 117.2 |
C4B—C5B—H5B | 105.0 | N1E—C2E—H2E1 | 109.3 |
C7B—C6B—C5B | 110.57 (13) | N1E—C2E—H2E2 | 109.6 |
C7B—C6B—H6B1 | 109.5 | H2E1—C2E—H2E2 | 109.4 |
C5B—C6B—H6B1 | 109.5 | N1E—C2E—H2E3 | 109.6 |
C7B—C6B—H6B2 | 109.6 | H2E1—C2E—H2E3 | 109.5 |
C5B—C6B—H6B2 | 109.5 | H2E2—C2E—H2E3 | 109.5 |
H6B1—C6B—H6B2 | 108.1 | N1E—C3E—H3E1 | 109.4 |
C8B—C7B—C6B | 111.30 (13) | N1E—C3E—H3E2 | 109.7 |
C8B—C7B—H7B1 | 109.4 | H3E1—C3E—H3E2 | 109.5 |
C6B—C7B—H7B1 | 109.4 | N1E—C3E—H3E3 | 109.3 |
C8B—C7B—H7B2 | 109.4 | H3E1—C3E—H3E3 | 109.5 |
C6B—C7B—H7B2 | 109.4 | H3E2—C3E—H3E3 | 109.5 |
H7B1—C7B—H7B2 | 108.0 | C1F—O1F—Na4 | 129.28 (14) |
C7B—C8B—C17B | 110.18 (13) | C1F—N1F—C3F | 121.89 (18) |
C7B—C8B—C9B | 110.06 (13) | C1F—N1F—C2F | 121.39 (18) |
C17B—C8B—C9B | 115.58 (14) | C3F—N1F—C2F | 116.67 (17) |
C7B—C8B—H8B | 106.9 | O1F—C1F—N1F | 126.19 (19) |
C17B—C8B—H8B | 106.9 | O1F—C1F—H1F | 116.9 |
C9B—C8B—H8B | 106.9 | N1F—C1F—H1F | 116.9 |
O3B—C9B—C11B | 104.96 (12) | N1F—C2F—H2F1 | 109.5 |
O3B—C9B—C8B | 107.96 (12) | N1F—C2F—H2F2 | 109.4 |
C11B—C9B—C8B | 111.98 (13) | H2F1—C2F—H2F2 | 109.5 |
O3B—C9B—C10B | 109.16 (12) | N1F—C2F—H2F3 | 109.5 |
C11B—C9B—C10B | 112.97 (12) | H2F1—C2F—H2F3 | 109.5 |
C8B—C9B—C10B | 109.57 (12) | H2F2—C2F—H2F3 | 109.4 |
C1B—C10B—C20B | 109.29 (13) | N1F—C3F—H3F1 | 109.5 |
C1B—C10B—C5B | 107.11 (12) | N1F—C3F—H3F2 | 109.4 |
C20B—C10B—C5B | 113.99 (13) | H3F1—C3F—H3F2 | 109.5 |
C1B—C10B—C9B | 109.93 (13) | N1F—C3F—H3F3 | 109.4 |
C20B—C10B—C9B | 108.26 (12) | H3F1—C3F—H3F3 | 109.5 |
C5B—C10B—C9B | 108.23 (12) | H3F2—C3F—H3F3 | 109.5 |
C12B—C11B—C9B | 105.23 (12) | Na1—O1W—H1W1 | 98.2 |
C12B—C11B—H11C | 110.7 | Na1—O1W—H1W2 | 111.7 |
C9B—C11B—H11C | 110.8 | H1W1—O1W—H1W2 | 104.4 |
C12B—C11B—H11D | 110.6 | Na1—O2W—H2W1 | 113.0 |
C9B—C11B—H11D | 110.6 | Na1—O2W—H2W2 | 101.3 |
H11C—C11B—H11D | 108.8 | H2W1—O2W—H2W2 | 104.5 |
C11B—C12B—C13B | 104.41 (12) | Na2—O3W—Na1 | 111.98 (6) |
C11B—C12B—H12C | 110.9 | Na2—O3W—H3W1 | 98.1 |
C13B—C12B—H12C | 110.8 | Na1—O3W—H3W1 | 116.5 |
C11B—C12B—H12D | 110.9 | Na2—O3W—H3W2 | 102.9 |
C13B—C12B—H12D | 110.8 | Na1—O3W—H3W2 | 120.0 |
H12C—C12B—H12D | 108.9 | H3W1—O3W—H3W2 | 104.4 |
O3B—C13B—C16B | 108.96 (12) | Na4i—O4W—Na2 | 138.21 (6) |
O3B—C13B—C14B | 105.84 (11) | Na4i—O4W—H4W1 | 114.0 |
C16B—C13B—C14B | 111.91 (13) | Na2—O4W—H4W1 | 87.5 |
O3B—C13B—C12B | 105.27 (12) | Na4i—O4W—H4W2 | 104.3 |
C16B—C13B—C12B | 109.77 (13) | Na2—O4W—H4W2 | 104.1 |
C14B—C13B—C12B | 114.67 (13) | H4W1—O4W—H4W2 | 104.4 |
C15B—C14B—C13B | 120.00 (13) | Na2—O5W—H5W1 | 130.4 |
C15B—C14B—H14C | 107.3 | Na2—O5W—H5W2 | 123.3 |
C13B—C14B—H14C | 107.4 | H5W1—O5W—H5W2 | 104.4 |
C15B—C14B—H14D | 107.3 | Na4—O6W—H6W1 | 127.0 |
C13B—C14B—H14D | 107.3 | Na4—O6W—H6W2 | 125.0 |
H14C—C14B—H14D | 106.9 | H6W1—O6W—H6W2 | 104.4 |
O5B—C15B—O6B | 123.34 (15) | H7W1—O7W—H7W2 | 104.4 |
O5B—C15B—C14B | 116.37 (14) | H8W1—O8W—H8W2 | 104.4 |
O6B—C15B—C14B | 120.28 (14) | | |
| | | |
C10A—C1A—C2A—C3A | −61.75 (18) | O1C—C3C—C4C—C19C | −47.42 (16) |
C1A—C2A—C3A—O1A | −176.19 (13) | C2C—C3C—C4C—C19C | 74.85 (16) |
C1A—C2A—C3A—C4A | 59.19 (18) | O1C—C3C—C4C—C18C | 67.01 (15) |
O1A—C3A—C4A—C19A | −45.47 (17) | C2C—C3C—C4C—C18C | −170.72 (12) |
C2A—C3A—C4A—C19A | 76.44 (17) | O1C—C3C—C4C—C5C | −174.23 (11) |
O1A—C3A—C4A—C18A | 70.60 (16) | C2C—C3C—C4C—C5C | −51.96 (16) |
C2A—C3A—C4A—C18A | −167.49 (13) | C19C—C4C—C5C—C6C | 54.66 (17) |
O1A—C3A—C4A—C5A | −171.99 (12) | C18C—C4C—C5C—C6C | −62.75 (16) |
C2A—C3A—C4A—C5A | −50.08 (17) | C3C—C4C—C5C—C6C | −179.70 (12) |
C19A—C4A—C5A—C6A | 51.39 (17) | C19C—C4C—C5C—C10C | −76.02 (17) |
C3A—C4A—C5A—C6A | 176.92 (13) | C18C—C4C—C5C—C10C | 166.58 (13) |
C18A—C4A—C5A—C6A | −66.30 (17) | C3C—C4C—C5C—C10C | 49.62 (16) |
C19A—C4A—C5A—C10A | −80.30 (17) | C4C—C5C—C6C—C7C | 170.38 (13) |
C3A—C4A—C5A—C10A | 45.23 (18) | C10C—C5C—C6C—C7C | −56.78 (17) |
C18A—C4A—C5A—C10A | 162.01 (13) | C5C—C6C—C7C—C8C | 56.37 (18) |
C4A—C5A—C6A—C7A | 166.18 (13) | C6C—C7C—C8C—C17C | 173.98 (14) |
C10A—C5A—C6A—C7A | −59.06 (17) | C6C—C7C—C8C—C9C | −57.90 (18) |
C5A—C6A—C7A—C8A | 54.88 (18) | C13C—O3C—C9C—C11C | 9.88 (15) |
C6A—C7A—C8A—C17A | 175.67 (14) | C13C—O3C—C9C—C8C | −109.87 (13) |
C6A—C7A—C8A—C9A | −55.12 (18) | C13C—O3C—C9C—C10C | 131.01 (12) |
C13A—O3A—C9A—C11A | 9.44 (15) | C7C—C8C—C9C—O3C | −59.32 (16) |
C13A—O3A—C9A—C8A | −109.92 (13) | C17C—C8C—C9C—O3C | 65.97 (17) |
C13A—O3A—C9A—C10A | 131.32 (12) | C7C—C8C—C9C—C11C | −174.30 (13) |
C7A—C8A—C9A—O3A | −58.60 (16) | C17C—C8C—C9C—C11C | −49.02 (18) |
C17A—C8A—C9A—O3A | 66.91 (17) | C7C—C8C—C9C—C10C | 58.87 (16) |
C7A—C8A—C9A—C11A | −173.34 (13) | C17C—C8C—C9C—C10C | −175.84 (13) |
C17A—C8A—C9A—C11A | −47.83 (18) | C2C—C1C—C10C—C20C | −67.96 (16) |
C7A—C8A—C9A—C10A | 58.77 (16) | C2C—C1C—C10C—C5C | 55.96 (16) |
C17A—C8A—C9A—C10A | −175.72 (13) | C2C—C1C—C10C—C9C | 173.97 (12) |
C2A—C1A—C10A—C20A | −71.14 (16) | C6C—C5C—C10C—C1C | 177.10 (12) |
C2A—C1A—C10A—C5A | 53.51 (16) | C4C—C5C—C10C—C1C | −51.33 (16) |
C2A—C1A—C10A—C9A | 169.50 (12) | C6C—C5C—C10C—C20C | −62.02 (16) |
C6A—C5A—C10A—C1A | −179.46 (12) | C4C—C5C—C10C—C20C | 69.55 (17) |
C4A—C5A—C10A—C1A | −46.78 (17) | C6C—C5C—C10C—C9C | 57.55 (15) |
C6A—C5A—C10A—C20A | −58.76 (16) | C4C—C5C—C10C—C9C | −170.88 (12) |
C4A—C5A—C10A—C20A | 73.92 (17) | O3C—C9C—C10C—C1C | −56.95 (15) |
C6A—C5A—C10A—C9A | 61.77 (15) | C11C—C9C—C10C—C1C | 58.35 (16) |
C4A—C5A—C10A—C9A | −165.55 (13) | C8C—C9C—C10C—C1C | −175.72 (12) |
O3A—C9A—C10A—C1A | −59.61 (15) | O3C—C9C—C10C—C20C | −175.85 (12) |
C11A—C9A—C10A—C1A | 55.55 (17) | C11C—C9C—C10C—C20C | −60.55 (17) |
C8A—C9A—C10A—C1A | −178.27 (12) | C8C—C9C—C10C—C20C | 65.38 (15) |
O3A—C9A—C10A—C20A | −178.33 (12) | O3C—C9C—C10C—C5C | 60.70 (15) |
C11A—C9A—C10A—C20A | −63.17 (16) | C11C—C9C—C10C—C5C | 176.00 (13) |
C8A—C9A—C10A—C20A | 63.01 (15) | C8C—C9C—C10C—C5C | −58.07 (15) |
O3A—C9A—C10A—C5A | 57.69 (14) | O3C—C9C—C11C—C12C | −22.14 (15) |
C11A—C9A—C10A—C5A | 172.85 (13) | C8C—C9C—C11C—C12C | 95.67 (15) |
C8A—C9A—C10A—C5A | −60.97 (15) | C10C—C9C—C11C—C12C | −139.63 (13) |
O3A—C9A—C11A—C12A | −23.53 (15) | C9C—C11C—C12C—C13C | 25.90 (16) |
C8A—C9A—C11A—C12A | 94.38 (15) | C9C—O3C—C13C—C16C | −111.85 (13) |
C10A—C9A—C11A—C12A | −140.48 (13) | C9C—O3C—C13C—C14C | 129.77 (12) |
C9A—C11A—C12A—C13A | 28.59 (16) | C9C—O3C—C13C—C12C | 6.43 (15) |
C9A—O3A—C13A—C14A | 132.02 (13) | C11C—C12C—C13C—O3C | −20.03 (15) |
C9A—O3A—C13A—C16A | −108.44 (14) | C11C—C12C—C13C—C16C | 98.12 (15) |
C9A—O3A—C13A—C12A | 8.61 (16) | C11C—C12C—C13C—C14C | −137.29 (14) |
C11A—C12A—C13A—O3A | −22.89 (16) | O3C—C13C—C14C—C15C | 167.55 (12) |
C11A—C12A—C13A—C14A | −137.83 (14) | C16C—C13C—C14C—C15C | 49.32 (17) |
C11A—C12A—C13A—C16A | 94.57 (15) | C12C—C13C—C14C—C15C | −75.26 (18) |
O3A—C13A—C14A—C15A | −175.72 (13) | C13C—C14C—C15C—O6C | 65.40 (19) |
C16A—C13A—C14A—C15A | 66.27 (19) | C13C—C14C—C15C—O5C | −114.79 (16) |
C12A—C13A—C14A—C15A | −59.9 (2) | C13C—C14C—C15C—Na4 | −32.9 (5) |
C13A—C14A—C15A—O5A | −176.36 (14) | O3C—C13C—C16C—O4C | −62.06 (15) |
C13A—C14A—C15A—O6A | 2.8 (2) | C14C—C13C—C16C—O4C | 54.09 (16) |
O3A—C13A—C16A—O4A | −51.79 (17) | C12C—C13C—C16C—O4C | −178.03 (12) |
C14A—C13A—C16A—O4A | 62.89 (17) | C19C—C4C—C18C—O2C | 174.32 (13) |
C12A—C13A—C16A—O4A | −166.72 (13) | C3C—C4C—C18C—O2C | 55.48 (16) |
C19A—C4A—C18A—O2A | 174.20 (13) | C5C—C4C—C18C—O2C | −62.97 (16) |
C3A—C4A—C18A—O2A | 54.87 (17) | C10D—C1D—C2D—C3D | −59.64 (17) |
C5A—C4A—C18A—O2A | −63.86 (17) | C1D—C2D—C3D—O1D | −176.30 (13) |
C10B—C1B—C2B—C3B | −59.07 (19) | C1D—C2D—C3D—C4D | 59.05 (17) |
C1B—C2B—C3B—O1B | −177.61 (14) | O1D—C3D—C4D—C19D | −50.15 (16) |
C1B—C2B—C3B—C4B | 58.35 (19) | C2D—C3D—C4D—C19D | 72.32 (16) |
O1B—C3B—C4B—C18B | 65.78 (16) | O1D—C3D—C4D—C18D | 63.70 (15) |
C2B—C3B—C4B—C18B | −172.34 (13) | C2D—C3D—C4D—C18D | −173.83 (12) |
O1B—C3B—C4B—C19B | −48.73 (18) | O1D—C3D—C4D—C5D | −176.52 (12) |
C2B—C3B—C4B—C19B | 73.15 (18) | C2D—C3D—C4D—C5D | −54.05 (16) |
O1B—C3B—C4B—C5B | −175.85 (12) | C19D—C4D—C5D—C6D | 56.58 (17) |
C2B—C3B—C4B—C5B | −53.97 (17) | C18D—C4D—C5D—C6D | −60.15 (17) |
C3B—C4B—C5B—C6B | −176.20 (13) | C3D—C4D—C5D—C6D | −178.53 (12) |
C18B—C4B—C5B—C6B | −58.57 (18) | C19D—C4D—C5D—C10D | −73.79 (17) |
C19B—C4B—C5B—C6B | 58.71 (18) | C18D—C4D—C5D—C10D | 169.48 (13) |
C3B—C4B—C5B—C10B | 52.95 (17) | C3D—C4D—C5D—C10D | 51.10 (16) |
C18B—C4B—C5B—C10B | 170.58 (14) | C4D—C5D—C6D—C7D | 171.40 (13) |
C19B—C4B—C5B—C10B | −72.14 (18) | C10D—C5D—C6D—C7D | −56.01 (17) |
C10B—C5B—C6B—C7B | −57.30 (17) | C5D—C6D—C7D—C8D | 55.47 (19) |
C4B—C5B—C6B—C7B | 169.80 (13) | C6D—C7D—C8D—C17D | 174.58 (14) |
C5B—C6B—C7B—C8B | 57.76 (17) | C6D—C7D—C8D—C9D | −57.41 (18) |
C6B—C7B—C8B—C17B | 172.11 (14) | C13D—O3D—C9D—C11D | 8.75 (15) |
C6B—C7B—C8B—C9B | −59.28 (17) | C13D—O3D—C9D—C8D | −110.81 (13) |
C13B—O3B—C9B—C11B | 6.25 (16) | C13D—O3D—C9D—C10D | 130.72 (12) |
C13B—O3B—C9B—C8B | −113.34 (13) | C7D—C8D—C9D—O3D | −58.83 (16) |
C13B—O3B—C9B—C10B | 127.62 (13) | C17D—C8D—C9D—O3D | 66.37 (17) |
C7B—C8B—C9B—O3B | −59.43 (16) | C7D—C8D—C9D—C11D | −173.71 (13) |
C17B—C8B—C9B—O3B | 66.16 (17) | C17D—C8D—C9D—C11D | −48.51 (19) |
C7B—C8B—C9B—C11B | −174.47 (12) | C7D—C8D—C9D—C10D | 59.04 (16) |
C17B—C8B—C9B—C11B | −48.89 (18) | C17D—C8D—C9D—C10D | −175.76 (13) |
C7B—C8B—C9B—C10B | 59.36 (16) | C2D—C1D—C10D—C20D | −69.94 (16) |
C17B—C8B—C9B—C10B | −175.05 (13) | C2D—C1D—C10D—C5D | 53.81 (16) |
C2B—C1B—C10B—C20B | −69.42 (16) | C2D—C1D—C10D—C9D | 172.49 (12) |
C2B—C1B—C10B—C5B | 54.53 (17) | C6D—C5D—C10D—C1D | 177.88 (12) |
C2B—C1B—C10B—C9B | 171.89 (13) | C4D—C5D—C10D—C1D | −50.59 (16) |
C6B—C5B—C10B—C1B | 175.55 (13) | C6D—C5D—C10D—C20D | −62.14 (17) |
C4B—C5B—C10B—C1B | −52.94 (17) | C4D—C5D—C10D—C20D | 69.39 (17) |
C6B—C5B—C10B—C20B | −63.43 (17) | C6D—C5D—C10D—C9D | 57.92 (16) |
C4B—C5B—C10B—C20B | 68.07 (18) | C4D—C5D—C10D—C9D | −170.55 (12) |
C6B—C5B—C10B—C9B | 57.08 (16) | O3D—C9D—C10D—C1D | −59.03 (15) |
C4B—C5B—C10B—C9B | −171.42 (13) | C11D—C9D—C10D—C1D | 56.84 (16) |
O3B—C9B—C10B—C1B | −56.23 (15) | C8D—C9D—C10D—C1D | −177.21 (12) |
C11B—C9B—C10B—C1B | 60.14 (16) | O3D—C9D—C10D—C20D | −176.82 (12) |
C8B—C9B—C10B—C1B | −174.27 (12) | C11D—C9D—C10D—C20D | −60.95 (17) |
O3B—C9B—C10B—C20B | −175.54 (12) | C8D—C9D—C10D—C20D | 65.00 (16) |
C11B—C9B—C10B—C20B | −59.18 (17) | O3D—C9D—C10D—C5D | 59.19 (15) |
C8B—C9B—C10B—C20B | 66.42 (16) | C11D—C9D—C10D—C5D | 175.06 (13) |
O3B—C9B—C10B—C5B | 60.44 (15) | C8D—C9D—C10D—C5D | −58.99 (15) |
C11B—C9B—C10B—C5B | 176.80 (13) | O3D—C9D—C11D—C12D | −21.86 (16) |
C8B—C9B—C10B—C5B | −57.60 (15) | C8D—C9D—C11D—C12D | 95.58 (15) |
O3B—C9B—C11B—C12B | −20.81 (16) | C10D—C9D—C11D—C12D | −139.88 (13) |
C8B—C9B—C11B—C12B | 96.06 (15) | C9D—C11D—C12D—C13D | 26.59 (16) |
C10B—C9B—C11B—C12B | −139.64 (13) | C9D—O3D—C13D—C16D | −109.88 (13) |
C9B—C11B—C12B—C13B | 27.16 (16) | C9D—O3D—C13D—C12D | 8.01 (16) |
C9B—O3B—C13B—C16B | −106.80 (14) | C9D—O3D—C13D—C14D | 131.59 (12) |
C9B—O3B—C13B—C14B | 132.70 (12) | C11D—C12D—C13D—O3D | −21.39 (16) |
C9B—O3B—C13B—C12B | 10.88 (16) | C11D—C12D—C13D—C16D | 95.49 (15) |
C11B—C12B—C13B—O3B | −23.37 (16) | C11D—C12D—C13D—C14D | −138.06 (14) |
C11B—C12B—C13B—C16B | 93.76 (15) | O3D—C13D—C14D—C15D | 165.28 (12) |
C11B—C12B—C13B—C14B | −139.27 (14) | C16D—C13D—C14D—C15D | 48.21 (17) |
O3B—C13B—C14B—C15B | −171.70 (13) | C12D—C13D—C14D—C15D | −77.91 (18) |
C16B—C13B—C14B—C15B | 69.74 (18) | C13D—C14D—C15D—O5D | −101.43 (17) |
C12B—C13B—C14B—C15B | −56.1 (2) | C13D—C14D—C15D—O6D | 79.17 (18) |
C13B—C14B—C15B—O5B | −177.70 (14) | O3D—C13D—C16D—O4D | −54.97 (16) |
C13B—C14B—C15B—O6B | 3.3 (2) | C12D—C13D—C16D—O4D | −170.19 (12) |
O3B—C13B—C16B—O4B | −49.82 (16) | C14D—C13D—C16D—O4D | 60.32 (16) |
C14B—C13B—C16B—O4B | 66.87 (17) | C19D—C4D—C18D—O2D | 172.40 (13) |
C12B—C13B—C16B—O4B | −164.63 (12) | C3D—C4D—C18D—O2D | 53.92 (16) |
C3B—C4B—C18B—O2B | 66.12 (17) | C5D—C4D—C18D—O2D | −65.02 (17) |
C19B—C4B—C18B—O2B | −174.97 (14) | C2E—N1E—C1E—O1E | 2.7 (3) |
C5B—C4B—C18B—O2B | −51.40 (19) | C3E—N1E—C1E—O1E | 179.8 (2) |
C10C—C1C—C2C—C3C | −60.64 (17) | C3F—N1F—C1F—O1F | −2.4 (3) |
C1C—C2C—C3C—O1C | −177.91 (13) | C2F—N1F—C1F—O1F | −180.0 (2) |
C1C—C2C—C3C—C4C | 57.88 (17) | | |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2OA···O2Wii | 0.82 | 2.14 | 2.8513 (17) | 145 |
O1A—H1A···O6Aii | 0.82 | 1.98 | 2.7797 (16) | 166 |
O4A—H4A···O6B | 0.82 | 1.89 | 2.7066 (17) | 173 |
O2B—H2OB···O2Di | 0.82 | 1.99 | 2.7717 (17) | 160 |
O1B—H1B···O6Bi | 0.82 | 2.02 | 2.8395 (18) | 174 |
O4B—H4B···O6A | 0.82 | 1.84 | 2.6347 (16) | 164 |
O4B—H4B···O5A | 0.82 | 2.66 | 3.2812 (17) | 134 |
O2C—H2OC···O6Ci | 0.82 | 2.03 | 2.8200 (17) | 162 |
O1C—H1C···O6Ci | 0.82 | 2.02 | 2.8198 (17) | 165 |
O4C—H4OC···O1E | 0.82 | 1.94 | 2.7494 (18) | 169 |
O2D—H2OD···O6Dii | 0.82 | 1.90 | 2.6949 (17) | 162 |
O1D—H1D···O6Dii | 0.82 | 2.06 | 2.8563 (17) | 166 |
O4D—H4OD···O6W | 0.82 | 2.14 | 2.8013 (17) | 138 |
O1W—H1W1···O4Ai | 0.85 | 1.97 | 2.717 (2) | 146 |
O1W—H1W2···O4B | 0.85 | 2.60 | 3.173 (2) | 125 |
O2W—H2W1···O3Ai | 0.85 | 2.25 | 3.0748 (17) | 163 |
O2W—H2W1···O4Ai | 0.85 | 2.57 | 3.1303 (18) | 125 |
O2W—H2W2···O5Ci | 0.85 | 1.94 | 2.7856 (17) | 176 |
O3W—H3W1···O4B | 0.85 | 1.95 | 2.7824 (18) | 166 |
O3W—H3W1···O3B | 0.85 | 2.79 | 3.3375 (18) | 124 |
O4W—H4W1···O6D | 0.85 | 1.96 | 2.8022 (18) | 169 |
O4W—H4W1···O5D | 0.85 | 2.55 | 3.0552 (16) | 119 |
O4W—H4W2···O1E | 0.85 | 2.11 | 2.9033 (19) | 156 |
O5W—H5W1···O4C | 0.85 | 2.22 | 2.8571 (19) | 131 |
O5W—H5W1···O3C | 0.85 | 2.50 | 3.2706 (18) | 152 |
O5W—H5W2···O2C | 0.85 | 2.00 | 2.8224 (18) | 163 |
O6W—H6W2···O2D | 0.85 | 2.13 | 2.9575 (17) | 163 |
O6W—H6W1···O5B | 0.85 | 2.00 | 2.7872 (17) | 154 |
O7W—H7W1···O1A | 0.85 | 2.09 | 2.9366 (19) | 175 |
O7W—H7W2···O1Ciii | 0.85 | 2.11 | 2.9577 (19) | 175 |
O8W—H8W2···O1B | 0.85 | 2.17 | 3.023 (2) | 176 |
O8W—H8W1···O1Div | 0.85 | 2.19 | 3.027 (2) | 171 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x+1, y, z−1; (iv) x−2, y, z−1. |
Experimental details
Crystal data |
Chemical formula | Na+·C20H33O6−·0.5C3H7NO·2H2O |
Mr | 465.04 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 130 |
a, b, c (Å) | 10.7614 (2), 31.0703 (5), 14.7131 (3) |
β (°) | 110.948 (2) |
V (Å3) | 4594.32 (15) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 1.01 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 |
|
Data collection |
Diffractometer | Oxford Diffraction SuperNova diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.655, 0.818 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 70056, 18050, 17865 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.631 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.086, 1.03 |
No. of reflections | 18050 |
No. of parameters | 1143 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.29 |
Absolute structure | Flack (1983), with 8192 Friedel pairs |
Absolute structure parameter | 0.03 (3) |
Selected bond lengths (Å) topNa1—O2B | 2.3488 (16) | Na3—O5D | 2.3479 (12) |
Na1—O1W | 2.3917 (18) | Na3—O5C | 2.3640 (12) |
Na1—O2W | 2.4151 (16) | Na3—O5A | 2.4036 (13) |
Na1—O3W | 2.5605 (16) | Na3—O4C | 2.5108 (14) |
Na1—O5Bi | 2.6656 (14) | Na3—O4D | 2.5130 (13) |
Na1—O6Bi | 2.9399 (15) | Na3—O5B | 2.5358 (14) |
Na2—O5A | 2.2860 (12) | Na4—O1F | 2.2610 (16) |
Na2—O5W | 2.3124 (16) | Na4—O4Wii | 2.2782 (14) |
Na2—O2Ai | 2.3841 (13) | Na4—O6W | 2.3304 (15) |
Na2—O5D | 2.3928 (13) | Na4—O5C | 2.3856 (13) |
Na2—O3W | 2.4779 (15) | Na4—O6C | 2.4619 (14) |
Na2—O4W | 2.5377 (14) | | |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2OA···O2Wii | 0.82 | 2.14 | 2.8513 (17) | 145 |
O1A—H1A···O6Aii | 0.82 | 1.98 | 2.7797 (16) | 166 |
O4A—H4A···O6B | 0.82 | 1.89 | 2.7066 (17) | 173 |
O2B—H2OB···O2Di | 0.82 | 1.99 | 2.7717 (17) | 160 |
O1B—H1B···O6Bi | 0.82 | 2.02 | 2.8395 (18) | 174 |
O4B—H4B···O6A | 0.82 | 1.84 | 2.6347 (16) | 164 |
O4B—H4B···O5A | 0.82 | 2.66 | 3.2812 (17) | 134 |
O2C—H2OC···O6Ci | 0.82 | 2.03 | 2.8200 (17) | 162 |
O1C—H1C···O6Ci | 0.82 | 2.02 | 2.8198 (17) | 165 |
O4C—H4OC···O1E | 0.82 | 1.94 | 2.7494 (18) | 169 |
O2D—H2OD···O6Dii | 0.82 | 1.90 | 2.6949 (17) | 162 |
O1D—H1D···O6Dii | 0.82 | 2.06 | 2.8563 (17) | 166 |
O4D—H4OD···O6W | 0.82 | 2.14 | 2.8013 (17) | 138 |
O1W—H1W1···O4Ai | 0.85 | 1.97 | 2.717 (2) | 146 |
O1W—H1W2···O4B | 0.85 | 2.60 | 3.173 (2) | 125 |
O2W—H2W1···O3Ai | 0.85 | 2.25 | 3.0748 (17) | 163 |
O2W—H2W1···O4Ai | 0.85 | 2.57 | 3.1303 (18) | 125 |
O2W—H2W2···O5Ci | 0.85 | 1.94 | 2.7856 (17) | 176 |
O3W—H3W1···O4B | 0.85 | 1.95 | 2.7824 (18) | 166 |
O3W—H3W1···O3B | 0.85 | 2.79 | 3.3375 (18) | 124 |
O4W—H4W1···O6D | 0.85 | 1.96 | 2.8022 (18) | 169 |
O4W—H4W1···O5D | 0.85 | 2.55 | 3.0552 (16) | 119 |
O4W—H4W2···O1E | 0.85 | 2.11 | 2.9033 (19) | 156 |
O5W—H5W1···O4C | 0.85 | 2.22 | 2.8571 (19) | 131 |
O5W—H5W1···O3C | 0.85 | 2.50 | 3.2706 (18) | 152 |
O5W—H5W2···O2C | 0.85 | 2.00 | 2.8224 (18) | 163 |
O6W—H6W2···O2D | 0.85 | 2.13 | 2.9575 (17) | 163 |
O6W—H6W1···O5B | 0.85 | 2.00 | 2.7872 (17) | 154 |
O7W—H7W1···O1A | 0.85 | 2.09 | 2.9366 (19) | 175 |
O7W—H7W2···O1Ciii | 0.85 | 2.11 | 2.9577 (19) | 175 |
O8W—H8W2···O1B | 0.85 | 2.17 | 3.023 (2) | 176 |
O8W—H8W1···O1Div | 0.85 | 2.19 | 3.027 (2) | 171 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x+1, y, z−1; (iv) x−2, y, z−1. |
Plants of the Lagochilus genus (family Lamiaceae), native to Central Asia and the Middle East, have long been used in traditional medicine and are reputed to possess antihaemorrhagic and haemostatic properties. The components responsible for these effects are labdane-type diterpenoids, many of which have been isolated from these plants and have shown haemostatic properties. Lagoden is a synthetic derivative of the naturally occurring diterpenoid lagochirsin (Zainutdinov et al., 1994), which has been isolated from three plants, namely L. gypsaceus, L. hirsutissimus and L. setulosus. It has been developed and approved for public use in Russia, Uzbekistan and some other former Soviet republics. Lagoden is produced as a white crystalline powder that is odourless and non-hygroscopic, and is sold as a 0.5% water solution in ampoules for internal introduction.
The crystal structures of lagochilin in its anhydrous and hydrated forms (Izotova et al., 1997; Vorontsova et al., 1975), lagochirsin (Izotova et al., 2004) and several other labdane-type diterpenoids isolated from plants of the Lagochilus genus, or their derivatives, have been reported over the years (Talipov et al., 2001; Izotova et al., 2000; Zainutdinov et al., 1999). Recently, we succeeded in growing single crystals of lagoden from a dimethylformamide (DMF) solution and we report its crystal structure here as the title compound, (I). Owing to the presence of Na+ ions, the absolute structure of (I) could be determined reliably using Cu Kα radiation.
Single crystals of lagoden proved very difficult to grow, despite efforts over a long time. In most cases, crystallizations resulted in amorphous glassy materials, but from a water–n-butanol mixture well shaped thin plates could be obtained repeatedly, although they diffracted very poorly. Serendipitously, a large prism of compound (I) was found in a small-scale crystallization from a DMF solution that had been left unattended for several months. The structure was initially determined at 100 K using Mo Kα radiation. As revealed by X-ray analysis, this crystal was a pseudomerohedral twin, with a twin law corresponding to a 180° rotation about the direct-space [100] direction (the twin matrix in reciprocal space is 1 0 0 0 -1 0 -0.991 0 -1.000). The structure refined well, revealing most of the important features of the crystal structure except the absolute configuration of lagoden, which was one of the objectives of the X-ray analysis. The anomalous signal originating mostly from Na (Δf'' = 0.025) and O atoms (Δf'' = 0.006) was too weak for reliable absolute structure determination, as reflected by the high s.u. value of the Flack parameter [x = 0.1 (3)] (Flack, 1983). Nevertheless, we noticed that the enantiomer indicated by the Flack parameter as the most probable had the expected chirality, with the C5, C9 and C10 centres corresponding to those of labdane, and the stereochemistry of the C8 and C13 centres being inverted. The Hooft parameter y (Hooft et al., 2008) for this enantiomerically pure crystal was 0.25 (9). As the anomalous dispersions of Na (Δf'' = 0.124) and O (Δf'' = 0.032) are significantly stronger for Cu Kα radiation, the measurements were repeated with an Oxford Diffraction Nova Cu Kα source with a small single crystal cut from the twinned specimen. The Flack parameter x = 0.03 (3) and the Hooft parameter y = 0.030 (8) for Cu Kα radiation indicated that the configurations of the C8 and C13 chiral centres of lagoden are R and S, respectively, and that the remaining centres correspond to the labdane stereochemistry. This feature is typical of all known structurally characterized diterpenoids of the Lagochilus genus, including its most popular member, lagochilin.
The asymmetric unit of compound (I) is shown in Figs. 1 and 2. It consists of four Na+ cations, four carboxylate anions, one DMF molecule and six water molecules coordinating to the Na+ ions, and three solvent molecules (one DMF and two water). The numbering scheme of the diterpenoid follows the IUPAC recommendation for the labdane skeleton (IUPAC Commission on Nomenclature of Organic Compounds, 1999). The four diterpenoid anions (A, B, C and D) exhibit similar conformations, with the largest differences found in the region of the spiro tetrahydrofurane ring and its substituents at C13. Analysis of the endocyclic torsion angles of the five-membered ring indicates a twist form, with the twist axis through atom O3 of the furanoid ring. The methyl substituents on the ring system at C4 and C10 are positioned axially, whereas the O1—H hydroxyl group and the C17 methyl group are in equatorial positions.
Na+ cations, anions and neutral ligands (one DMF and six water molecules) are assembled via dipolar interactions [Na—O distances in the range 2.2860 (12)–2.6656 (14) Å; Table 1] and O—H···O hydrogen bonds (Table 2) into a one-dimensional polymeric structure propagating along the a axis. The hydrophobic parts of the diterpenoid cover the polymer surface on two opposite sides, leaving deep grooves on the remaining two sides. Adjacent polymeric chains along the c axis are bridged by two water molecules, O7W and O8W, which are involved as donors in O—H···O hydrogen bonds to the secondary O1—H hydroxyl groups of the four symmetry-independent anions. In effect, the grooves on opposite sides of the polymer meet to form a channel accommodating both the coordinated and hydrogen-bonded DMF molecules (Fig. 3).
The Na+ cations and their coordinating groups are shown in Fig. 4. The coordination environments of ions Na2 and Na3 are distorted octahedral, with carboxylate atoms O5D and O5A bridging the two metal centres. Cation Na3 has in its coordination sphere exclusively O ligands from four symmetry-independent lagoden anions, whereas ion Na2 has three water molecules and O atoms from anions A and D. These two Na ions, together with ions Na1 and Na4, carboxylate atoms O5C and O5B, and the water molecules O3W and O4W, form a cyclic Na4O4 structure (Fig. 4). Cations Na1 and Na4 are basically pentacoordinated, with ion Na1 additionally including in its coordination environment atom O6B from the asymmetrically chelating carboxylate group of anion B [Na1—O6B(x - 1, y, z) = 2.9399 (15) Å]. The closest distances between the Na ions along the polymeric chain are 3.4807 (8) Å within the Na2O2 cyclic structures and 3.9845 (9) Å in the Na4O4 ring. The Na—O—Na angles at the bridging O atoms range from 94.48 (5)° in the smaller ring up to 138.21 (6)° in the eight-membered cycle.
Lagoden anions C and D act as chelating ligands by coordinating ion Na3 via a carboxylate O atom and the primary hydroxyl group at C16. The seven-membered chelate rings that are formed are strongly puckered. The other two ligands coordinate to Na cations via a carboxylate group and the primary hydroxyl group at C18. The coordination mode of the carboxylate groups of ligands B and C is asymmetric chelating and bridging, whereas in the remaining cases it is only bridging. The secondary OH groups at C3 do not interact with the Na+ ions but act as donors in O—H···O hydrogen bonds to carboxylate groups within the same polymeric structure, and as acceptors of hydrogen bonds from water molecules that bridge adjacent polymeric chains via O—H···O interactions (Table 2).