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The crystal structure of the title compound, [Na(C36H61O11)]·2H2O, was first reported by Duax et al. [J. Am. Chem. Soc. (1980), 102, 6725-6729]. We report here the crystal structure of a new polymorph, determined at the low temperature of 180 (2) K, in the same orthorhombic non-centrosymmetric space group P212121. The structure contains one crystallographically unique sodium monensin complex, showing a highly distorted octahedral coordination environment for Na+, forming undulating layers in the ac plane. H atoms from the pendant hydroxyl groups involved in head-to-tail hydrogen bonding with the carboxyl­ate group and from the crystallization water mol­ecules occupying the interlayer spaces have been successfully located in difference Fourier maps.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022980/ac6066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022980/ac6066Isup2.hkl
Contains datablock I

CCDC reference: 226667

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.062
  • wR factor = 0.168
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.19 Ratio PLAT731_ALERT_1_B Bond Calc 0.99(8), Rep 0.988(10) ...... 8.00 su-Rat O13 -H13A 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.98(5), Rep 0.986(10) ...... 5.00 su-Rat O13 -H13B 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.98(5), Rep 0.986(10) ...... 5.00 su-Rat O13 -H13B 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.99(8), Rep 0.988(10) ...... 8.00 su-Rat O13 -H13A 1.555 1.555
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.37 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C22 - C23 = 5.24 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT417_ALERT_2_C Short Inter D-H..H-D H5 .. H13B = 2.12 Ang. PLAT731_ALERT_1_C Bond Calc 0.85(5), Rep 0.84(2) ...... 2.50 su-Rat O10 -H10 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.91(5), Rep 0.91(2) ...... 2.50 su-Rat O12 -H12D 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 108(5), Rep 108(2) ...... 2.50 su-Rat H13A -O13 -H13B 1.555 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(5), Rep 0.84(2) ...... 2.50 su-Rat O10 -H10 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.91(5), Rep 0.91(2) ...... 2.50 su-Rat O12 -H12D 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.81(6), Rep 1.81(2) ...... 3.00 su-Rat H10 -O1 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 4873 Count of symmetry unique reflns 4956 Completeness (_total/calc) 98.33% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 6 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare at al., 1994); program(s) used to refine structure: SHELXTL (Bruker 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Sodium monensin dihydrate top
Crystal data top
[Na(C36H61O11)]·2H2OF(000) = 1584
Mr = 728.87Dx = 1.241 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 73775 reflections
a = 12.4768 (4) Åθ = 1.0–27.5°
b = 14.1024 (4) ŵ = 0.10 mm1
c = 22.1653 (7) ÅT = 180 K
V = 3900.0 (2) Å3Block, colourless
Z = 40.46 × 0.12 × 0.07 mm
Data collection top
Nonius KappaCCD
diffractometer
4132 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Thin–slice ω and φ scansθmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1616
Tmin = 0.937, Tmax = 0.984k = 1218
14637 measured reflectionsl = 2828
4873 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0807P)2 + 2.259P]
where P = (Fo2 + 2Fc2)/3
4873 reflections(Δ/σ)max < 0.001
472 parametersΔρmax = 0.69 e Å3
16 restraintsΔρmin = 0.56 e Å3
Special details top

Experimental. A total of 3597 Friedel pairs have been merged before refinement. Flack (1983) parameter was found to be meaningless (the compound is a weak anomalous scatterer). This parameter was removed from the CIF listing.

H-atoms bound to carbon were placed in calculated positions. H-atoms connected to O5 and O10 were located in difference Fourier maps and the corresponding O–H distances were restrained to be 0.84 (2) A. The H bound to O11 could also be directly located but in order to get the best hydrogen bond fitting to O2 it was instead placed in a calculated position using the HFIX 147 instruction.

H-atoms from O12 and O13 water molecules were located in difference Fourier maps, and refined with the O—H and the H···H distances restrained in order to ensure a chemically reasonable geometry for these molecules.

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
xyzUiso*/Ueq
Na10.37446 (13)0.67912 (12)0.78266 (7)0.0361 (4)
O10.2401 (2)0.8772 (2)0.66451 (15)0.0438 (8)
O20.3039 (2)0.7590 (2)0.60858 (13)0.0335 (6)
O30.0164 (2)0.7368 (2)0.54377 (13)0.0349 (6)
O40.0571 (2)0.61075 (19)0.73815 (12)0.0291 (6)
O50.3321 (2)0.5593 (2)0.71392 (14)0.0379 (7)
O60.1961 (2)0.63715 (19)0.80692 (12)0.0300 (6)
O70.3311 (2)0.7158 (2)0.89122 (13)0.0362 (6)
O80.5096 (2)0.60757 (19)0.84964 (13)0.0344 (6)
O90.5616 (2)0.71847 (19)0.75835 (13)0.0323 (6)
O100.3891 (2)0.8362 (2)0.74513 (14)0.0386 (7)
O110.4813 (2)0.70342 (19)0.66535 (14)0.0370 (7)
H110.42480.73220.65600.055*
H50.368 (4)0.569 (4)0.6824 (17)0.060 (17)*
H100.348 (5)0.850 (5)0.716 (2)0.10 (3)*
C10.2335 (3)0.8196 (3)0.62232 (17)0.0291 (8)
C20.1310 (3)0.8227 (3)0.58338 (18)0.0309 (8)
H20.08160.87150.60070.037*
C30.1603 (3)0.8524 (3)0.51880 (19)0.0377 (9)
H3A0.09470.86050.49500.057*
H3B0.20510.80330.50030.057*
H3C0.19990.91240.51990.057*
C40.0735 (3)0.7264 (3)0.58442 (17)0.0264 (7)
H40.12310.67720.56780.032*
C50.0515 (4)0.6497 (3)0.5179 (2)0.0404 (10)
H5A0.09530.61510.54720.061*
H5B0.01090.61130.50690.061*
H5C0.09420.66290.48170.061*
C60.0322 (3)0.6924 (3)0.64645 (17)0.0272 (8)
H60.02670.64620.63800.033*
C70.0186 (3)0.7736 (3)0.68237 (19)0.0338 (9)
H7A0.03730.81810.69510.051*
H7B0.05480.74780.71810.051*
H7C0.07090.80670.65700.051*
C80.1156 (3)0.6391 (3)0.68446 (16)0.0264 (7)
H80.17430.68380.69610.032*
C90.1648 (3)0.5505 (3)0.65516 (18)0.0316 (8)
H90.20900.57170.62000.038*
C100.0813 (4)0.4790 (3)0.6319 (2)0.0409 (10)
H10A0.02980.46490.66400.061*
H10B0.11760.42040.61960.061*
H10C0.04350.50610.59720.061*
C110.2396 (3)0.5024 (3)0.70038 (19)0.0331 (8)
H11A0.26380.44040.68320.040*
C120.1827 (4)0.4841 (3)0.76001 (19)0.0355 (9)
H12A0.13250.43030.75470.043*
H12B0.23650.46510.79050.043*
C130.1208 (3)0.5687 (3)0.78365 (18)0.0310 (8)
C140.0476 (4)0.5475 (3)0.83669 (19)0.0403 (10)
H14A0.02460.52820.82280.048*
H14B0.07780.49660.86240.048*
C150.0434 (4)0.6409 (4)0.8703 (2)0.0460 (11)
H15A0.03370.63010.91410.055*
H15B0.01640.68060.85530.055*
C160.1514 (3)0.6888 (3)0.85778 (18)0.0342 (9)
C170.1409 (4)0.7925 (3)0.8409 (2)0.0444 (10)
H17A0.09460.79850.80540.067*
H17B0.21180.81850.83170.067*
H17C0.10930.82760.87470.067*
C180.2304 (4)0.6761 (3)0.9101 (2)0.0402 (10)
H180.20360.71180.94600.048*
C190.2593 (5)0.5760 (4)0.9291 (2)0.0512 (12)
H19A0.25820.53230.89420.061*
H19B0.20900.55230.96020.061*
C200.3730 (4)0.5855 (3)0.9548 (2)0.0438 (10)
H20A0.41960.53380.93980.053*
H20B0.37180.58340.99940.053*
C210.4135 (4)0.6826 (3)0.9323 (2)0.0417 (10)
C220.4213 (6)0.7546 (4)0.9850 (2)0.0617 (15)
H22A0.48230.73671.01120.074*
H22B0.35520.75061.00950.074*
C230.4368 (7)0.8595 (5)0.9639 (4)0.089 (2)
H23A0.38490.87410.93200.134*
H23B0.50970.86780.94820.134*
H23C0.42560.90230.99810.134*
C240.5139 (4)0.6824 (3)0.89411 (19)0.0372 (9)
H240.51530.74380.87160.045*
C250.6243 (4)0.6699 (4)0.9231 (2)0.0507 (12)
H250.64640.72960.94410.061*
C260.6359 (5)0.5853 (4)0.9654 (3)0.0614 (15)
H26A0.63210.52640.94210.092*
H26B0.57790.58640.99530.092*
H26C0.70510.58880.98620.092*
C270.6909 (4)0.6559 (4)0.8650 (2)0.0472 (12)
H27A0.70840.71760.84600.057*
H27B0.75830.62140.87350.057*
C280.6163 (3)0.5967 (3)0.8242 (2)0.0366 (9)
H280.63780.52850.82660.044*
C290.6128 (3)0.6270 (3)0.7577 (2)0.0328 (9)
H290.56620.58160.73500.039*
C300.7222 (3)0.6317 (3)0.7268 (2)0.0373 (10)
H300.77120.67110.75220.045*
C310.7712 (4)0.5325 (4)0.7201 (3)0.0534 (13)
H31A0.84390.53800.70370.080*
H31B0.72710.49460.69260.080*
H31C0.77390.50160.75960.080*
C320.7097 (3)0.6798 (3)0.6655 (2)0.0375 (9)
H32A0.78130.68810.64700.045*
H32B0.66690.63850.63860.045*
C330.6552 (3)0.7761 (3)0.6707 (2)0.0352 (9)
H330.69990.81650.69790.042*
C340.6468 (4)0.8268 (4)0.6099 (2)0.0497 (12)
H34A0.59390.79450.58460.075*
H34B0.71680.82590.58990.075*
H34C0.62440.89270.61640.075*
C350.5459 (3)0.7626 (3)0.70096 (19)0.0313 (8)
C360.4888 (3)0.8548 (3)0.7160 (2)0.0367 (9)
H36A0.53470.89370.74270.044*
H36B0.47590.89120.67840.044*
O120.3464 (3)0.6274 (3)0.51765 (16)0.0548 (9)
H12D0.388 (5)0.657 (4)0.490 (2)0.082*
H12E0.332 (5)0.666 (3)0.5488 (18)0.082*
O130.4467 (7)0.5232 (6)0.6072 (3)0.139 (3)
H13A0.406 (9)0.527 (4)0.569 (3)0.208*
H13B0.484 (6)0.584 (3)0.613 (3)0.208*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0287 (7)0.0431 (9)0.0366 (8)0.0011 (7)0.0017 (7)0.0046 (7)
O10.0366 (15)0.0435 (16)0.0512 (19)0.0050 (14)0.0121 (14)0.0155 (15)
O20.0249 (12)0.0411 (15)0.0346 (14)0.0031 (12)0.0032 (11)0.0043 (12)
O30.0245 (12)0.0364 (14)0.0436 (16)0.0019 (12)0.0122 (12)0.0007 (13)
O40.0255 (12)0.0331 (13)0.0286 (13)0.0033 (11)0.0028 (11)0.0003 (11)
O50.0277 (13)0.0485 (17)0.0374 (16)0.0052 (14)0.0027 (12)0.0035 (14)
O60.0295 (13)0.0310 (13)0.0294 (14)0.0012 (12)0.0018 (11)0.0023 (11)
O70.0394 (15)0.0355 (14)0.0337 (15)0.0021 (13)0.0031 (12)0.0019 (12)
O80.0313 (14)0.0359 (14)0.0361 (15)0.0026 (13)0.0073 (12)0.0034 (12)
O90.0287 (13)0.0292 (13)0.0391 (15)0.0020 (12)0.0032 (12)0.0056 (12)
O100.0312 (15)0.0412 (16)0.0432 (17)0.0059 (13)0.0034 (13)0.0018 (14)
O110.0288 (14)0.0304 (13)0.0518 (18)0.0006 (12)0.0113 (13)0.0045 (13)
C10.0244 (16)0.0304 (18)0.0325 (19)0.0030 (16)0.0021 (15)0.0034 (16)
C20.0230 (16)0.0327 (19)0.037 (2)0.0006 (17)0.0023 (16)0.0006 (16)
C30.0314 (19)0.043 (2)0.039 (2)0.0059 (19)0.0074 (17)0.0091 (19)
C40.0195 (15)0.0302 (18)0.0296 (18)0.0015 (15)0.0043 (14)0.0027 (15)
C50.038 (2)0.043 (2)0.041 (2)0.008 (2)0.0118 (19)0.0007 (19)
C60.0216 (16)0.0275 (17)0.0324 (19)0.0003 (15)0.0001 (14)0.0006 (15)
C70.0260 (17)0.0335 (19)0.042 (2)0.0047 (17)0.0044 (17)0.0012 (17)
C80.0217 (15)0.0288 (17)0.0288 (18)0.0003 (15)0.0040 (14)0.0013 (15)
C90.0332 (19)0.0306 (18)0.031 (2)0.0034 (17)0.0034 (16)0.0003 (16)
C100.046 (2)0.035 (2)0.041 (2)0.001 (2)0.005 (2)0.0070 (18)
C110.037 (2)0.0250 (17)0.037 (2)0.0062 (17)0.0008 (17)0.0034 (16)
C120.042 (2)0.0292 (18)0.035 (2)0.0010 (18)0.0030 (18)0.0053 (17)
C130.0332 (19)0.0273 (17)0.0324 (19)0.0002 (16)0.0011 (17)0.0045 (15)
C140.043 (2)0.044 (2)0.034 (2)0.006 (2)0.0040 (19)0.0054 (18)
C150.040 (2)0.063 (3)0.036 (2)0.003 (2)0.0123 (19)0.000 (2)
C160.035 (2)0.041 (2)0.0267 (19)0.0040 (18)0.0035 (16)0.0045 (17)
C170.044 (2)0.041 (2)0.048 (3)0.010 (2)0.002 (2)0.006 (2)
C180.045 (2)0.045 (2)0.030 (2)0.005 (2)0.0055 (18)0.0033 (18)
C190.065 (3)0.049 (3)0.040 (3)0.008 (3)0.006 (2)0.013 (2)
C200.054 (3)0.044 (2)0.033 (2)0.004 (2)0.004 (2)0.0057 (19)
C210.052 (3)0.041 (2)0.033 (2)0.002 (2)0.0100 (19)0.0013 (18)
C220.091 (4)0.057 (3)0.037 (3)0.013 (3)0.011 (3)0.007 (2)
C230.105 (6)0.073 (4)0.089 (5)0.001 (4)0.025 (5)0.021 (4)
C240.046 (2)0.034 (2)0.031 (2)0.002 (2)0.0149 (19)0.0010 (17)
C250.050 (3)0.052 (3)0.050 (3)0.006 (2)0.027 (2)0.006 (2)
C260.060 (3)0.068 (3)0.057 (3)0.001 (3)0.023 (3)0.021 (3)
C270.035 (2)0.047 (3)0.060 (3)0.007 (2)0.020 (2)0.009 (2)
C280.0291 (19)0.0318 (19)0.049 (2)0.0001 (17)0.0058 (18)0.0051 (18)
C290.0256 (18)0.0265 (18)0.046 (2)0.0001 (16)0.0031 (17)0.0066 (17)
C300.0215 (17)0.036 (2)0.054 (3)0.0019 (16)0.0005 (18)0.0062 (19)
C310.035 (2)0.045 (3)0.080 (4)0.008 (2)0.016 (2)0.022 (3)
C320.0243 (18)0.036 (2)0.052 (3)0.0034 (17)0.0056 (17)0.008 (2)
C330.0291 (18)0.0304 (18)0.046 (2)0.0039 (17)0.0005 (18)0.0081 (18)
C340.049 (3)0.047 (3)0.053 (3)0.006 (2)0.008 (2)0.017 (2)
C350.0279 (18)0.0272 (17)0.039 (2)0.0011 (16)0.0060 (16)0.0002 (16)
C360.0331 (19)0.0292 (18)0.048 (2)0.0002 (18)0.0075 (19)0.0029 (18)
O120.061 (2)0.054 (2)0.050 (2)0.0113 (18)0.0108 (18)0.0094 (17)
O130.132 (6)0.182 (7)0.102 (4)0.055 (5)0.051 (4)0.042 (5)
Geometric parameters (Å, º) top
Na1—O52.336 (4)C15—C161.533 (6)
Na1—O62.365 (3)C15—H15A0.9900
Na1—O102.373 (3)C15—H15B0.9900
Na1—O92.459 (3)C16—C171.515 (6)
Na1—O82.463 (3)C16—C181.532 (6)
Na1—O72.520 (3)C17—H17A0.9800
O1—C11.242 (5)C17—H17B0.9800
O2—C11.263 (5)C17—H17C0.9800
O3—C51.425 (5)C18—C191.516 (7)
O3—C41.447 (4)C18—H181.0000
O4—C131.415 (5)C19—C201.535 (7)
O4—C81.452 (4)C19—H19A0.9900
O5—C111.438 (5)C19—H19B0.9900
O5—H50.84 (2)C20—C211.543 (7)
O6—C131.442 (5)C20—H20A0.9900
O6—C161.453 (5)C20—H20B0.9900
O7—C181.438 (5)C21—C241.512 (7)
O7—C211.451 (5)C21—C221.551 (7)
O8—C241.445 (5)C22—C231.563 (9)
O8—C281.454 (5)C22—H22A0.9900
O9—C351.430 (5)C22—H22B0.9900
O9—C291.439 (5)C23—H23A0.9800
O10—C361.426 (5)C23—H23B0.9800
O10—H100.84 (2)C23—H23C0.9800
O11—C351.403 (5)C24—C251.531 (6)
O11—H110.8400C24—H241.0000
C1—C21.543 (5)C25—C261.524 (7)
C2—C41.535 (5)C25—C271.546 (8)
C2—C31.536 (6)C25—H251.0000
C2—H21.0000C26—H26A0.9800
C3—H3A0.9800C26—H26B0.9800
C3—H3B0.9800C26—H26C0.9800
C3—H3C0.9800C27—C281.543 (6)
C4—C61.545 (5)C27—H27A0.9900
C4—H41.0000C27—H27B0.9900
C5—H5A0.9800C28—C291.535 (6)
C5—H5B0.9800C28—H281.0000
C5—H5C0.9800C29—C301.529 (5)
C6—C71.531 (5)C29—H291.0000
C6—C81.536 (5)C30—C321.526 (6)
C6—H61.0000C30—C311.534 (7)
C7—H7A0.9800C30—H301.0000
C7—H7B0.9800C31—H31A0.9800
C7—H7C0.9800C31—H31B0.9800
C8—C91.536 (5)C31—H31C0.9800
C8—H81.0000C32—C331.524 (6)
C9—C111.528 (6)C32—H32A0.9900
C9—C101.539 (6)C32—H32B0.9900
C9—H91.0000C33—C341.528 (6)
C10—H10A0.9800C33—C351.532 (6)
C10—H10B0.9800C33—H331.0000
C10—H10C0.9800C34—H34A0.9800
C11—C121.522 (6)C34—H34B0.9800
C11—H11A1.0000C34—H34C0.9800
C12—C131.515 (6)C35—C361.520 (5)
C12—H12A0.9900C36—H36A0.9900
C12—H12B0.9900C36—H36B0.9900
C13—C141.518 (6)O12—H12D0.91 (2)
C14—C151.515 (7)O12—H12E0.90 (2)
C14—H14A0.9900O13—H13A0.988 (10)
C14—H14B0.9900O13—H13B0.986 (10)
O5—Na1—O675.79 (11)O6—C16—C18106.3 (3)
O5—Na1—O10117.65 (13)C17—C16—C18110.9 (4)
O6—Na1—O10112.69 (12)C15—C16—C18112.1 (4)
O5—Na1—O9103.59 (12)C16—C17—H17A109.5
O6—Na1—O9178.44 (12)C16—C17—H17B109.5
O10—Na1—O968.87 (10)H17A—C17—H17B109.5
O5—Na1—O8104.57 (12)C16—C17—H17C109.5
O6—Na1—O8113.87 (11)H17A—C17—H17C109.5
O10—Na1—O8122.75 (12)H17B—C17—H17C109.5
O9—Na1—O864.82 (10)O7—C18—C19103.7 (4)
O5—Na1—O7136.28 (13)O7—C18—C16107.2 (3)
O6—Na1—O768.42 (10)C19—C18—C16118.2 (4)
O10—Na1—O799.19 (12)O7—C18—H18109.1
O9—Na1—O7111.51 (12)C19—C18—H18109.1
O8—Na1—O769.84 (10)C16—C18—H18109.1
C5—O3—C4113.7 (3)C18—C19—C20104.0 (4)
C13—O4—C8114.6 (3)C18—C19—H19A111.0
C11—O5—Na1136.2 (2)C20—C19—H19A111.0
C11—O5—H5111 (4)C18—C19—H19B111.0
Na1—O5—H5107 (4)C20—C19—H19B111.0
C13—O6—C16111.3 (3)H19A—C19—H19B109.0
C13—O6—Na1134.3 (2)C19—C20—C21105.1 (4)
C16—O6—Na1114.3 (2)C19—C20—H20A110.7
C18—O7—C21108.1 (3)C21—C20—H20A110.7
C18—O7—Na1112.7 (2)C19—C20—H20B110.7
C21—O7—Na1112.4 (2)C21—C20—H20B110.7
C24—O8—C28107.9 (3)H20A—C20—H20B108.8
C24—O8—Na197.9 (2)O7—C21—C24103.6 (3)
C28—O8—Na1115.8 (2)O7—C21—C20104.9 (4)
C35—O9—C29116.2 (3)C24—C21—C20116.8 (4)
C35—O9—Na199.4 (2)O7—C21—C22107.9 (4)
C29—O9—Na1102.8 (2)C24—C21—C22111.8 (4)
C36—O10—Na1113.5 (2)C20—C21—C22111.0 (4)
C36—O10—H1099 (5)C21—C22—C23113.7 (5)
Na1—O10—H10115 (5)C21—C22—H22A108.8
C35—O11—H11109.5C23—C22—H22A108.8
O1—C1—O2125.3 (4)C21—C22—H22B108.8
O1—C1—C2117.2 (3)C23—C22—H22B108.8
O2—C1—C2117.4 (3)H22A—C22—H22B107.7
C4—C2—C3111.5 (3)C22—C23—H23A109.5
C4—C2—C1110.7 (3)C22—C23—H23B109.5
C3—C2—C1109.3 (3)H23A—C23—H23B109.5
C4—C2—H2108.4C22—C23—H23C109.5
C3—C2—H2108.4H23A—C23—H23C109.5
C1—C2—H2108.4H23B—C23—H23C109.5
C2—C3—H3A109.5O8—C24—C21110.7 (3)
C2—C3—H3B109.5O8—C24—C25103.6 (4)
H3A—C3—H3B109.5C21—C24—C25120.7 (4)
C2—C3—H3C109.5O8—C24—H24107.0
H3A—C3—H3C109.5C21—C24—H24107.0
H3B—C3—H3C109.5C25—C24—H24107.0
O3—C4—C2105.3 (3)C26—C25—C24115.7 (4)
O3—C4—C6109.1 (3)C26—C25—C27111.2 (5)
C2—C4—C6116.3 (3)C24—C25—C2798.5 (4)
O3—C4—H4108.6C26—C25—H25110.3
C2—C4—H4108.6C24—C25—H25110.3
C6—C4—H4108.6C27—C25—H25110.3
O3—C5—H5A109.5C25—C26—H26A109.5
O3—C5—H5B109.5C25—C26—H26B109.5
H5A—C5—H5B109.5H26A—C26—H26B109.5
O3—C5—H5C109.5C25—C26—H26C109.5
H5A—C5—H5C109.5H26A—C26—H26C109.5
H5B—C5—H5C109.5H26B—C26—H26C109.5
C7—C6—C8111.2 (3)C28—C27—C25103.5 (4)
C7—C6—C4111.7 (3)C28—C27—H27A111.1
C8—C6—C4114.5 (3)C25—C27—H27A111.1
C7—C6—H6106.3C28—C27—H27B111.1
C8—C6—H6106.3C25—C27—H27B111.1
C4—C6—H6106.3H27A—C27—H27B109.0
C6—C7—H7A109.5O8—C28—C29108.5 (3)
C6—C7—H7B109.5O8—C28—C27105.6 (4)
H7A—C7—H7B109.5C29—C28—C27115.4 (4)
C6—C7—H7C109.5O8—C28—H28109.1
H7A—C7—H7C109.5C29—C28—H28109.1
H7B—C7—H7C109.5C27—C28—H28109.1
O4—C8—C6104.1 (3)O9—C29—C30111.2 (3)
O4—C8—C9108.9 (3)O9—C29—C28104.6 (3)
C6—C8—C9115.9 (3)C30—C29—C28114.6 (3)
O4—C8—H8109.2O9—C29—H29108.7
C6—C8—H8109.2C30—C29—H29108.7
C9—C8—H8109.2C28—C29—H29108.7
C11—C9—C8109.1 (3)C32—C30—C29109.1 (3)
C11—C9—C10110.0 (3)C32—C30—C31111.1 (4)
C8—C9—C10113.9 (3)C29—C30—C31111.1 (3)
C11—C9—H9107.9C32—C30—H30108.5
C8—C9—H9107.9C29—C30—H30108.5
C10—C9—H9107.9C31—C30—H30108.5
C9—C10—H10A109.5C30—C31—H31A109.5
C9—C10—H10B109.5C30—C31—H31B109.5
H10A—C10—H10B109.5H31A—C31—H31B109.5
C9—C10—H10C109.5C30—C31—H31C109.5
H10A—C10—H10C109.5H31A—C31—H31C109.5
H10B—C10—H10C109.5H31B—C31—H31C109.5
O5—C11—C12106.7 (3)C33—C32—C30112.0 (4)
O5—C11—C9112.3 (3)C33—C32—H32A109.2
C12—C11—C9111.1 (3)C30—C32—H32A109.2
O5—C11—H11A108.9C33—C32—H32B109.2
C12—C11—H11A108.9C30—C32—H32B109.2
C9—C11—H11A108.9H32A—C32—H32B107.9
C13—C12—C11113.8 (3)C32—C33—C34112.4 (4)
C13—C12—H12A108.8C32—C33—C35108.6 (3)
C11—C12—H12A108.8C34—C33—C35112.6 (3)
C13—C12—H12B108.8C32—C33—H33107.7
C11—C12—H12B108.8C34—C33—H33107.7
H12A—C12—H12B107.7C35—C33—H33107.7
O4—C13—O6109.9 (3)C33—C34—H34A109.5
O4—C13—C12111.7 (3)C33—C34—H34B109.5
O6—C13—C12108.6 (3)H34A—C34—H34B109.5
O4—C13—C14107.3 (3)C33—C34—H34C109.5
O6—C13—C14104.3 (3)H34A—C34—H34C109.5
C12—C13—C14114.7 (3)H34B—C34—H34C109.5
C15—C14—C13103.3 (3)O11—C35—O9108.7 (3)
C15—C14—H14A111.1O11—C35—C36111.3 (3)
C13—C14—H14A111.1O9—C35—C36104.0 (3)
C15—C14—H14B111.1O11—C35—C33109.8 (3)
C13—C14—H14B111.1O9—C35—C33108.8 (3)
H14A—C14—H14B109.1C36—C35—C33114.0 (3)
C14—C15—C16105.3 (4)O10—C36—C35110.5 (3)
C14—C15—H15A110.7O10—C36—H36A109.6
C16—C15—H15A110.7C35—C36—H36A109.6
C14—C15—H15B110.7O10—C36—H36B109.6
C16—C15—H15B110.7C35—C36—H36B109.6
H15A—C15—H15B108.8H36A—C36—H36B108.1
O6—C16—C17109.0 (3)H12D—O12—H12E110 (3)
O6—C16—C15104.8 (3)H13A—O13—H13B108 (2)
C17—C16—C15113.2 (4)
O6—Na1—O5—C111.9 (4)O6—C13—C14—C1532.8 (4)
O10—Na1—O5—C11106.5 (4)C12—C13—C14—C15151.5 (4)
O9—Na1—O5—C11179.5 (3)C13—C14—C15—C1629.6 (5)
O8—Na1—O5—C11113.4 (4)C13—O6—C16—C17115.7 (4)
O7—Na1—O5—C1137.5 (4)Na1—O6—C16—C1766.0 (4)
O5—Na1—O6—C130.7 (3)C13—O6—C16—C155.7 (4)
O10—Na1—O6—C13115.1 (3)Na1—O6—C16—C15172.5 (3)
O8—Na1—O6—C1399.2 (3)C13—O6—C16—C18124.7 (3)
O7—Na1—O6—C13153.7 (3)Na1—O6—C16—C1853.6 (4)
O5—Na1—O6—C16178.4 (3)C14—C15—C16—O615.4 (4)
O10—Na1—O6—C1667.2 (3)C14—C15—C16—C17134.1 (4)
O8—Na1—O6—C1678.5 (3)C14—C15—C16—C1899.5 (4)
O7—Na1—O6—C1624.0 (2)C21—O7—C18—C1939.1 (4)
O5—Na1—O7—C1827.0 (3)Na1—O7—C18—C1985.7 (3)
O6—Na1—O7—C1810.3 (3)C21—O7—C18—C16164.9 (3)
O10—Na1—O7—C18121.2 (3)Na1—O7—C18—C1640.1 (4)
O9—Na1—O7—C18168.0 (3)O6—C16—C18—O760.7 (4)
O8—Na1—O7—C18117.2 (3)C17—C16—C18—O757.7 (4)
O5—Na1—O7—C2195.5 (3)C15—C16—C18—O7174.8 (4)
O6—Na1—O7—C21132.7 (3)O6—C16—C18—C1955.8 (5)
O10—Na1—O7—C21116.4 (3)C17—C16—C18—C19174.2 (4)
O9—Na1—O7—C2145.6 (3)C15—C16—C18—C1958.2 (5)
O8—Na1—O7—C215.2 (3)O7—C18—C19—C2033.0 (5)
O5—Na1—O8—C24171.1 (2)C16—C18—C19—C20151.4 (4)
O6—Na1—O8—C2490.4 (2)C18—C19—C20—C2115.8 (5)
O10—Na1—O8—C2451.4 (3)C18—O7—C21—C24151.6 (3)
O9—Na1—O8—C2490.5 (2)Na1—O7—C21—C2426.6 (4)
O7—Na1—O8—C2436.6 (2)C18—O7—C21—C2028.7 (4)
O5—Na1—O8—C2874.6 (3)Na1—O7—C21—C2096.3 (3)
O6—Na1—O8—C28155.2 (2)C18—O7—C21—C2289.8 (4)
O10—Na1—O8—C2862.9 (3)Na1—O7—C21—C22145.3 (3)
O9—Na1—O8—C2823.8 (2)C19—C20—C21—O76.7 (5)
O7—Na1—O8—C28151.0 (3)C19—C20—C21—C24120.8 (4)
O5—Na1—O9—C3569.6 (2)C19—C20—C21—C22109.6 (5)
O10—Na1—O9—C3545.2 (2)O7—C21—C22—C2352.7 (7)
O8—Na1—O9—C35169.5 (2)C24—C21—C22—C2360.6 (7)
O7—Na1—O9—C35137.0 (2)C20—C21—C22—C23167.1 (6)
O5—Na1—O9—C2950.2 (2)C28—O8—C24—C21167.0 (3)
O10—Na1—O9—C29164.9 (3)Na1—O8—C24—C2172.5 (3)
O8—Na1—O9—C2949.7 (2)C28—O8—C24—C2536.3 (4)
O7—Na1—O9—C29103.2 (2)Na1—O8—C24—C25156.8 (3)
O5—Na1—O10—C3679.4 (3)O7—C21—C24—O870.6 (4)
O6—Na1—O10—C36164.7 (3)C20—C21—C24—O844.2 (5)
O9—Na1—O10—C3615.3 (3)C22—C21—C24—O8173.5 (4)
O8—Na1—O10—C3653.0 (3)O7—C21—C24—C25168.3 (4)
O7—Na1—O10—C36124.9 (3)C20—C21—C24—C2576.9 (5)
O1—C1—C2—C4121.7 (4)C22—C21—C24—C2552.4 (6)
O2—C1—C2—C458.6 (4)O8—C24—C25—C2673.4 (5)
O1—C1—C2—C3115.1 (4)C21—C24—C25—C2651.1 (6)
O2—C1—C2—C364.6 (4)O8—C24—C25—C2745.2 (4)
C5—O3—C4—C2154.0 (3)C21—C24—C25—C27169.7 (4)
C5—O3—C4—C680.5 (4)C26—C25—C27—C2884.3 (4)
C3—C2—C4—O354.6 (4)C24—C25—C27—C2837.6 (4)
C1—C2—C4—O3176.6 (3)C24—O8—C28—C29113.1 (3)
C3—C2—C4—C6175.5 (3)Na1—O8—C28—C294.7 (4)
C1—C2—C4—C662.5 (4)C24—O8—C28—C2711.1 (4)
O3—C4—C6—C777.3 (4)Na1—O8—C28—C27119.6 (3)
C2—C4—C6—C741.5 (4)C25—C27—C28—O817.9 (4)
O3—C4—C6—C8155.3 (3)C25—C27—C28—C29137.7 (4)
C2—C4—C6—C885.9 (4)C35—O9—C29—C3057.0 (4)
C13—O4—C8—C6173.4 (3)Na1—O9—C29—C30164.4 (3)
C13—O4—C8—C962.3 (4)C35—O9—C29—C28178.7 (3)
C7—C6—C8—O455.2 (4)Na1—O9—C29—C2871.3 (3)
C4—C6—C8—O4177.2 (3)O8—C28—C29—O950.4 (4)
C7—C6—C8—C9174.7 (3)C27—C28—C29—O967.8 (4)
C4—C6—C8—C957.6 (4)O8—C28—C29—C30172.5 (3)
O4—C8—C9—C1159.1 (4)C27—C28—C29—C3054.4 (5)
C6—C8—C9—C11176.0 (3)O9—C29—C30—C3251.1 (5)
O4—C8—C9—C1064.2 (4)C28—C29—C30—C32169.6 (3)
C6—C8—C9—C1052.7 (4)O9—C29—C30—C31173.9 (4)
Na1—O5—C11—C1234.6 (5)C28—C29—C30—C3167.7 (5)
Na1—O5—C11—C987.4 (4)C29—C30—C32—C3353.9 (4)
C8—C9—C11—O566.7 (4)C31—C30—C32—C33176.7 (3)
C10—C9—C11—O5167.7 (3)C30—C32—C33—C34177.4 (4)
C8—C9—C11—C1252.7 (4)C30—C32—C33—C3557.4 (4)
C10—C9—C11—C1272.8 (4)C29—O9—C35—O1159.9 (4)
O5—C11—C12—C1375.5 (4)Na1—O9—C35—O1149.4 (3)
C9—C11—C12—C1347.2 (5)C29—O9—C35—C36178.6 (3)
C8—O4—C13—O665.1 (4)Na1—O9—C35—C3669.3 (3)
C8—O4—C13—C1255.6 (4)C29—O9—C35—C3359.5 (4)
C8—O4—C13—C14177.8 (3)Na1—O9—C35—C33168.9 (3)
C16—O6—C13—O490.2 (3)C32—C33—C35—O1161.5 (4)
Na1—O6—C13—O492.0 (4)C34—C33—C35—O1163.6 (4)
C16—O6—C13—C12147.3 (3)C32—C33—C35—O957.3 (4)
Na1—O6—C13—C1230.5 (4)C34—C33—C35—O9177.6 (3)
C16—O6—C13—C1424.5 (4)C32—C33—C35—C36172.8 (4)
Na1—O6—C13—C14153.3 (3)C34—C33—C35—C3662.1 (5)
C11—C12—C13—O447.2 (5)Na1—O10—C36—C3516.2 (4)
C11—C12—C13—O674.2 (4)O11—C35—C36—O1056.4 (5)
C11—C12—C13—C14169.5 (4)O9—C35—C36—O1060.4 (4)
O4—C13—C14—C1583.7 (4)C33—C35—C36—O10178.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O130.84 (2)2.04 (3)2.810 (7)152 (5)
O10—H10···O10.84 (2)1.81 (2)2.643 (4)170 (8)
O11—H11···O20.841.882.665 (4)156
O12—H12E···O20.90 (2)1.90 (2)2.791 (4)174 (5)
O12—H12D···O3i0.91 (2)2.05 (3)2.907 (4)157 (5)
O13—H13B···O110.99 (1)2.04 (5)2.882 (10)142 (6)
O13—H13A···O120.99 (1)1.96 (4)2.769 (8)137 (5)
Symmetry code: (i) x+1/2, y+3/2, z+1.
 

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