Sodium monensin dihydrate

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.

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

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Computing details

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

Crystal data

[Na(C36H61O11)]·2H2O	F(000) = 1584
Mr = 728.87	Dx = 1.241 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 73775 reflections
a = 12.4768 (4) Å	θ = 1.0–27.5°
b = 14.1024 (4) Å	µ = 0.10 mm^−1
c = 22.1653 (7) Å	T = 180 K
V = 3900.0 (2) Å^3	Block, colourless
Z = 4	0.46 × 0.12 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer	4132 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Thin–slice ω and φ scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −16→16
Tmin = 0.937, Tmax = 0.984	k = −12→18
14637 measured reflections	l = −28→28
4873 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0807P)^2 + 2.259P] where P = (Fo^2 + 2Fc^2)/3
4873 reflections	(Δ/σ)max < 0.001
472 parameters	Δρmax = 0.69 e Å^−3
16 restraints	Δρmin = −0.56 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Na1	0.37446 (13)	0.67912 (12)	0.78266 (7)	0.0361 (4)
O1	0.2401 (2)	0.8772 (2)	0.66451 (15)	0.0438 (8)
O2	0.3039 (2)	0.7590 (2)	0.60858 (13)	0.0335 (6)
O3	−0.0164 (2)	0.7368 (2)	0.54377 (13)	0.0349 (6)
O4	0.0571 (2)	0.61075 (19)	0.73815 (12)	0.0291 (6)
O5	0.3321 (2)	0.5593 (2)	0.71392 (14)	0.0379 (7)
O6	0.1961 (2)	0.63715 (19)	0.80692 (12)	0.0300 (6)
O7	0.3311 (2)	0.7158 (2)	0.89122 (13)	0.0362 (6)
O8	0.5096 (2)	0.60757 (19)	0.84964 (13)	0.0344 (6)
O9	0.5616 (2)	0.71847 (19)	0.75835 (13)	0.0323 (6)
O10	0.3891 (2)	0.8362 (2)	0.74513 (14)	0.0386 (7)
O11	0.4813 (2)	0.70342 (19)	0.66535 (14)	0.0370 (7)
H11	0.4248	0.7322	0.6560	0.055*
H5	0.368 (4)	0.569 (4)	0.6824 (17)	0.060 (17)*
H10	0.348 (5)	0.850 (5)	0.716 (2)	0.10 (3)*
C1	0.2335 (3)	0.8196 (3)	0.62232 (17)	0.0291 (8)
C2	0.1310 (3)	0.8227 (3)	0.58338 (18)	0.0309 (8)
H2	0.0816	0.8715	0.6007	0.037*
C3	0.1603 (3)	0.8524 (3)	0.51880 (19)	0.0377 (9)
H3A	0.0947	0.8605	0.4950	0.057*
H3B	0.2051	0.8033	0.5003	0.057*
H3C	0.1999	0.9124	0.5199	0.057*
C4	0.0735 (3)	0.7264 (3)	0.58442 (17)	0.0264 (7)
H4	0.1231	0.6772	0.5678	0.032*
C5	−0.0515 (4)	0.6497 (3)	0.5179 (2)	0.0404 (10)
H5A	−0.0953	0.6151	0.5472	0.061*
H5B	0.0109	0.6113	0.5069	0.061*
H5C	−0.0942	0.6629	0.4817	0.061*
C6	0.0322 (3)	0.6924 (3)	0.64645 (17)	0.0272 (8)
H6	−0.0267	0.6462	0.6380	0.033*
C7	−0.0186 (3)	0.7736 (3)	0.68237 (19)	0.0338 (9)
H7A	0.0373	0.8181	0.6951	0.051*
H7B	−0.0548	0.7478	0.7181	0.051*
H7C	−0.0709	0.8067	0.6570	0.051*
C8	0.1156 (3)	0.6391 (3)	0.68446 (16)	0.0264 (7)
H8	0.1743	0.6838	0.6961	0.032*
C9	0.1648 (3)	0.5505 (3)	0.65516 (18)	0.0316 (8)
H9	0.2090	0.5717	0.6200	0.038*
C10	0.0813 (4)	0.4790 (3)	0.6319 (2)	0.0409 (10)
H10A	0.0298	0.4649	0.6640	0.061*
H10B	0.1176	0.4204	0.6196	0.061*
H10C	0.0435	0.5061	0.5972	0.061*
C11	0.2396 (3)	0.5024 (3)	0.70038 (19)	0.0331 (8)
H11A	0.2638	0.4404	0.6832	0.040*
C12	0.1827 (4)	0.4841 (3)	0.76001 (19)	0.0355 (9)
H12A	0.1325	0.4303	0.7547	0.043*
H12B	0.2365	0.4651	0.7905	0.043*
C13	0.1208 (3)	0.5687 (3)	0.78365 (18)	0.0310 (8)
C14	0.0476 (4)	0.5475 (3)	0.83669 (19)	0.0403 (10)
H14A	−0.0246	0.5282	0.8228	0.048*
H14B	0.0778	0.4966	0.8624	0.048*
C15	0.0434 (4)	0.6409 (4)	0.8703 (2)	0.0460 (11)
H15A	0.0337	0.6301	0.9141	0.055*
H15B	−0.0164	0.6806	0.8553	0.055*
C16	0.1514 (3)	0.6888 (3)	0.85778 (18)	0.0342 (9)
C17	0.1409 (4)	0.7925 (3)	0.8409 (2)	0.0444 (10)
H17A	0.0946	0.7985	0.8054	0.067*
H17B	0.2118	0.8185	0.8317	0.067*
H17C	0.1093	0.8276	0.8747	0.067*
C18	0.2304 (4)	0.6761 (3)	0.9101 (2)	0.0402 (10)
H18	0.2036	0.7118	0.9460	0.048*
C19	0.2593 (5)	0.5760 (4)	0.9291 (2)	0.0512 (12)
H19A	0.2582	0.5323	0.8942	0.061*
H19B	0.2090	0.5523	0.9602	0.061*
C20	0.3730 (4)	0.5855 (3)	0.9548 (2)	0.0438 (10)
H20A	0.4196	0.5338	0.9398	0.053*
H20B	0.3718	0.5834	0.9994	0.053*
C21	0.4135 (4)	0.6826 (3)	0.9323 (2)	0.0417 (10)
C22	0.4213 (6)	0.7546 (4)	0.9850 (2)	0.0617 (15)
H22A	0.4823	0.7367	1.0112	0.074*
H22B	0.3552	0.7506	1.0095	0.074*
C23	0.4368 (7)	0.8595 (5)	0.9639 (4)	0.089 (2)
H23A	0.3849	0.8741	0.9320	0.134*
H23B	0.5097	0.8678	0.9482	0.134*
H23C	0.4256	0.9023	0.9981	0.134*
C24	0.5139 (4)	0.6824 (3)	0.89411 (19)	0.0372 (9)
H24	0.5153	0.7438	0.8716	0.045*
C25	0.6243 (4)	0.6699 (4)	0.9231 (2)	0.0507 (12)
H25	0.6464	0.7296	0.9441	0.061*
C26	0.6359 (5)	0.5853 (4)	0.9654 (3)	0.0614 (15)
H26A	0.6321	0.5264	0.9421	0.092*
H26B	0.5779	0.5864	0.9953	0.092*
H26C	0.7051	0.5888	0.9862	0.092*
C27	0.6909 (4)	0.6559 (4)	0.8650 (2)	0.0472 (12)
H27A	0.7084	0.7176	0.8460	0.057*
H27B	0.7583	0.6214	0.8735	0.057*
C28	0.6163 (3)	0.5967 (3)	0.8242 (2)	0.0366 (9)
H28	0.6378	0.5285	0.8266	0.044*
C29	0.6128 (3)	0.6270 (3)	0.7577 (2)	0.0328 (9)
H29	0.5662	0.5816	0.7350	0.039*
C30	0.7222 (3)	0.6317 (3)	0.7268 (2)	0.0373 (10)
H30	0.7712	0.6711	0.7522	0.045*
C31	0.7712 (4)	0.5325 (4)	0.7201 (3)	0.0534 (13)
H31A	0.8439	0.5380	0.7037	0.080*
H31B	0.7271	0.4946	0.6926	0.080*
H31C	0.7739	0.5016	0.7596	0.080*
C32	0.7097 (3)	0.6798 (3)	0.6655 (2)	0.0375 (9)
H32A	0.7813	0.6881	0.6470	0.045*
H32B	0.6669	0.6385	0.6386	0.045*
C33	0.6552 (3)	0.7761 (3)	0.6707 (2)	0.0352 (9)
H33	0.6999	0.8165	0.6979	0.042*
C34	0.6468 (4)	0.8268 (4)	0.6099 (2)	0.0497 (12)
H34A	0.5939	0.7945	0.5846	0.075*
H34B	0.7168	0.8259	0.5899	0.075*
H34C	0.6244	0.8927	0.6164	0.075*
C35	0.5459 (3)	0.7626 (3)	0.70096 (19)	0.0313 (8)
C36	0.4888 (3)	0.8548 (3)	0.7160 (2)	0.0367 (9)
H36A	0.5347	0.8937	0.7427	0.044*
H36B	0.4759	0.8912	0.6784	0.044*
O12	0.3464 (3)	0.6274 (3)	0.51765 (16)	0.0548 (9)
H12D	0.388 (5)	0.657 (4)	0.490 (2)	0.082*
H12E	0.332 (5)	0.666 (3)	0.5488 (18)	0.082*
O13	0.4467 (7)	0.5232 (6)	0.6072 (3)	0.139 (3)
H13A	0.406 (9)	0.527 (4)	0.569 (3)	0.208*
H13B	0.484 (6)	0.584 (3)	0.613 (3)	0.208*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0287 (7)	0.0431 (9)	0.0366 (8)	−0.0011 (7)	−0.0017 (7)	0.0046 (7)
O1	0.0366 (15)	0.0435 (16)	0.0512 (19)	0.0050 (14)	−0.0121 (14)	−0.0155 (15)
O2	0.0249 (12)	0.0411 (15)	0.0346 (14)	0.0031 (12)	−0.0032 (11)	−0.0043 (12)
O3	0.0245 (12)	0.0364 (14)	0.0436 (16)	0.0019 (12)	−0.0122 (12)	−0.0007 (13)
O4	0.0255 (12)	0.0331 (13)	0.0286 (13)	−0.0033 (11)	0.0028 (11)	0.0003 (11)
O5	0.0277 (13)	0.0485 (17)	0.0374 (16)	0.0052 (14)	0.0027 (12)	0.0035 (14)
O6	0.0295 (13)	0.0310 (13)	0.0294 (14)	−0.0012 (12)	0.0018 (11)	−0.0023 (11)
O7	0.0394 (15)	0.0355 (14)	0.0337 (15)	0.0021 (13)	−0.0031 (12)	−0.0019 (12)
O8	0.0313 (14)	0.0359 (14)	0.0361 (15)	−0.0026 (13)	−0.0073 (12)	0.0034 (12)
O9	0.0287 (13)	0.0292 (13)	0.0391 (15)	0.0020 (12)	−0.0032 (12)	0.0056 (12)
O10	0.0312 (15)	0.0412 (16)	0.0432 (17)	0.0059 (13)	−0.0034 (13)	−0.0018 (14)
O11	0.0288 (14)	0.0304 (13)	0.0518 (18)	0.0006 (12)	−0.0113 (13)	−0.0045 (13)
C1	0.0244 (16)	0.0304 (18)	0.0325 (19)	−0.0030 (16)	−0.0021 (15)	0.0034 (16)
C2	0.0230 (16)	0.0327 (19)	0.037 (2)	0.0006 (17)	−0.0023 (16)	0.0006 (16)
C3	0.0314 (19)	0.043 (2)	0.039 (2)	−0.0059 (19)	−0.0074 (17)	0.0091 (19)
C4	0.0195 (15)	0.0302 (18)	0.0296 (18)	0.0015 (15)	−0.0043 (14)	−0.0027 (15)
C5	0.038 (2)	0.043 (2)	0.041 (2)	−0.008 (2)	−0.0118 (19)	−0.0007 (19)
C6	0.0216 (16)	0.0275 (17)	0.0324 (19)	−0.0003 (15)	−0.0001 (14)	0.0006 (15)
C7	0.0260 (17)	0.0335 (19)	0.042 (2)	0.0047 (17)	0.0044 (17)	0.0012 (17)
C8	0.0217 (15)	0.0288 (17)	0.0288 (18)	0.0003 (15)	0.0040 (14)	0.0013 (15)
C9	0.0332 (19)	0.0306 (18)	0.031 (2)	0.0034 (17)	0.0034 (16)	−0.0003 (16)
C10	0.046 (2)	0.035 (2)	0.041 (2)	0.001 (2)	−0.005 (2)	−0.0070 (18)
C11	0.037 (2)	0.0250 (17)	0.037 (2)	0.0062 (17)	−0.0008 (17)	−0.0034 (16)
C12	0.042 (2)	0.0292 (18)	0.035 (2)	−0.0010 (18)	−0.0030 (18)	0.0053 (17)
C13	0.0332 (19)	0.0273 (17)	0.0324 (19)	0.0002 (16)	0.0011 (17)	0.0045 (15)
C14	0.043 (2)	0.044 (2)	0.034 (2)	−0.006 (2)	0.0040 (19)	0.0054 (18)
C15	0.040 (2)	0.063 (3)	0.036 (2)	−0.003 (2)	0.0123 (19)	0.000 (2)
C16	0.035 (2)	0.041 (2)	0.0267 (19)	0.0040 (18)	0.0035 (16)	−0.0045 (17)
C17	0.044 (2)	0.041 (2)	0.048 (3)	0.010 (2)	0.002 (2)	−0.006 (2)
C18	0.045 (2)	0.045 (2)	0.030 (2)	−0.005 (2)	0.0055 (18)	−0.0033 (18)
C19	0.065 (3)	0.049 (3)	0.040 (3)	−0.008 (3)	−0.006 (2)	0.013 (2)
C20	0.054 (3)	0.044 (2)	0.033 (2)	0.004 (2)	−0.004 (2)	0.0057 (19)
C21	0.052 (3)	0.041 (2)	0.033 (2)	−0.002 (2)	−0.0100 (19)	−0.0013 (18)
C22	0.091 (4)	0.057 (3)	0.037 (3)	−0.013 (3)	−0.011 (3)	−0.007 (2)
C23	0.105 (6)	0.073 (4)	0.089 (5)	0.001 (4)	−0.025 (5)	−0.021 (4)
C24	0.046 (2)	0.034 (2)	0.031 (2)	−0.002 (2)	−0.0149 (19)	0.0010 (17)
C25	0.050 (3)	0.052 (3)	0.050 (3)	−0.006 (2)	−0.027 (2)	0.006 (2)
C26	0.060 (3)	0.068 (3)	0.057 (3)	0.001 (3)	−0.023 (3)	0.021 (3)
C27	0.035 (2)	0.047 (3)	0.060 (3)	−0.007 (2)	−0.020 (2)	0.009 (2)
C28	0.0291 (19)	0.0318 (19)	0.049 (2)	0.0001 (17)	−0.0058 (18)	0.0051 (18)
C29	0.0256 (18)	0.0265 (18)	0.046 (2)	0.0001 (16)	−0.0031 (17)	0.0066 (17)
C30	0.0215 (17)	0.036 (2)	0.054 (3)	−0.0019 (16)	−0.0005 (18)	0.0062 (19)
C31	0.035 (2)	0.045 (3)	0.080 (4)	0.008 (2)	0.016 (2)	0.022 (3)
C32	0.0243 (18)	0.036 (2)	0.052 (3)	−0.0034 (17)	0.0056 (17)	0.008 (2)
C33	0.0291 (18)	0.0304 (18)	0.046 (2)	−0.0039 (17)	−0.0005 (18)	0.0081 (18)
C34	0.049 (3)	0.047 (3)	0.053 (3)	0.006 (2)	0.008 (2)	0.017 (2)
C35	0.0279 (18)	0.0272 (17)	0.039 (2)	−0.0011 (16)	−0.0060 (16)	−0.0002 (16)
C36	0.0331 (19)	0.0292 (18)	0.048 (2)	−0.0002 (18)	−0.0075 (19)	0.0029 (18)
O12	0.061 (2)	0.054 (2)	0.050 (2)	−0.0113 (18)	0.0108 (18)	−0.0094 (17)
O13	0.132 (6)	0.182 (7)	0.102 (4)	0.055 (5)	0.051 (4)	0.042 (5)

Geometric parameters (Å, º)

Na1—O5	2.336 (4)	C15—C16	1.533 (6)
Na1—O6	2.365 (3)	C15—H15A	0.9900
Na1—O10	2.373 (3)	C15—H15B	0.9900
Na1—O9	2.459 (3)	C16—C17	1.515 (6)
Na1—O8	2.463 (3)	C16—C18	1.532 (6)
Na1—O7	2.520 (3)	C17—H17A	0.9800
O1—C1	1.242 (5)	C17—H17B	0.9800
O2—C1	1.263 (5)	C17—H17C	0.9800
O3—C5	1.425 (5)	C18—C19	1.516 (7)
O3—C4	1.447 (4)	C18—H18	1.0000
O4—C13	1.415 (5)	C19—C20	1.535 (7)
O4—C8	1.452 (4)	C19—H19A	0.9900
O5—C11	1.438 (5)	C19—H19B	0.9900
O5—H5	0.84 (2)	C20—C21	1.543 (7)
O6—C13	1.442 (5)	C20—H20A	0.9900
O6—C16	1.453 (5)	C20—H20B	0.9900
O7—C18	1.438 (5)	C21—C24	1.512 (7)
O7—C21	1.451 (5)	C21—C22	1.551 (7)
O8—C24	1.445 (5)	C22—C23	1.563 (9)
O8—C28	1.454 (5)	C22—H22A	0.9900
O9—C35	1.430 (5)	C22—H22B	0.9900
O9—C29	1.439 (5)	C23—H23A	0.9800
O10—C36	1.426 (5)	C23—H23B	0.9800
O10—H10	0.84 (2)	C23—H23C	0.9800
O11—C35	1.403 (5)	C24—C25	1.531 (6)
O11—H11	0.8400	C24—H24	1.0000
C1—C2	1.543 (5)	C25—C26	1.524 (7)
C2—C4	1.535 (5)	C25—C27	1.546 (8)
C2—C3	1.536 (6)	C25—H25	1.0000
C2—H2	1.0000	C26—H26A	0.9800
C3—H3A	0.9800	C26—H26B	0.9800
C3—H3B	0.9800	C26—H26C	0.9800
C3—H3C	0.9800	C27—C28	1.543 (6)
C4—C6	1.545 (5)	C27—H27A	0.9900
C4—H4	1.0000	C27—H27B	0.9900
C5—H5A	0.9800	C28—C29	1.535 (6)
C5—H5B	0.9800	C28—H28	1.0000
C5—H5C	0.9800	C29—C30	1.529 (5)
C6—C7	1.531 (5)	C29—H29	1.0000
C6—C8	1.536 (5)	C30—C32	1.526 (6)
C6—H6	1.0000	C30—C31	1.534 (7)
C7—H7A	0.9800	C30—H30	1.0000
C7—H7B	0.9800	C31—H31A	0.9800
C7—H7C	0.9800	C31—H31B	0.9800
C8—C9	1.536 (5)	C31—H31C	0.9800
C8—H8	1.0000	C32—C33	1.524 (6)
C9—C11	1.528 (6)	C32—H32A	0.9900
C9—C10	1.539 (6)	C32—H32B	0.9900
C9—H9	1.0000	C33—C34	1.528 (6)
C10—H10A	0.9800	C33—C35	1.532 (6)
C10—H10B	0.9800	C33—H33	1.0000
C10—H10C	0.9800	C34—H34A	0.9800
C11—C12	1.522 (6)	C34—H34B	0.9800
C11—H11A	1.0000	C34—H34C	0.9800
C12—C13	1.515 (6)	C35—C36	1.520 (5)
C12—H12A	0.9900	C36—H36A	0.9900
C12—H12B	0.9900	C36—H36B	0.9900
C13—C14	1.518 (6)	O12—H12D	0.91 (2)
C14—C15	1.515 (7)	O12—H12E	0.90 (2)
C14—H14A	0.9900	O13—H13A	0.988 (10)
C14—H14B	0.9900	O13—H13B	0.986 (10)
O5—Na1—O6	75.79 (11)	O6—C16—C18	106.3 (3)
O5—Na1—O10	117.65 (13)	C17—C16—C18	110.9 (4)
O6—Na1—O10	112.69 (12)	C15—C16—C18	112.1 (4)
O5—Na1—O9	103.59 (12)	C16—C17—H17A	109.5
O6—Na1—O9	178.44 (12)	C16—C17—H17B	109.5
O10—Na1—O9	68.87 (10)	H17A—C17—H17B	109.5
O5—Na1—O8	104.57 (12)	C16—C17—H17C	109.5
O6—Na1—O8	113.87 (11)	H17A—C17—H17C	109.5
O10—Na1—O8	122.75 (12)	H17B—C17—H17C	109.5
O9—Na1—O8	64.82 (10)	O7—C18—C19	103.7 (4)
O5—Na1—O7	136.28 (13)	O7—C18—C16	107.2 (3)
O6—Na1—O7	68.42 (10)	C19—C18—C16	118.2 (4)
O10—Na1—O7	99.19 (12)	O7—C18—H18	109.1
O9—Na1—O7	111.51 (12)	C19—C18—H18	109.1
O8—Na1—O7	69.84 (10)	C16—C18—H18	109.1
C5—O3—C4	113.7 (3)	C18—C19—C20	104.0 (4)
C13—O4—C8	114.6 (3)	C18—C19—H19A	111.0
C11—O5—Na1	136.2 (2)	C20—C19—H19A	111.0
C11—O5—H5	111 (4)	C18—C19—H19B	111.0
Na1—O5—H5	107 (4)	C20—C19—H19B	111.0
C13—O6—C16	111.3 (3)	H19A—C19—H19B	109.0
C13—O6—Na1	134.3 (2)	C19—C20—C21	105.1 (4)
C16—O6—Na1	114.3 (2)	C19—C20—H20A	110.7
C18—O7—C21	108.1 (3)	C21—C20—H20A	110.7
C18—O7—Na1	112.7 (2)	C19—C20—H20B	110.7
C21—O7—Na1	112.4 (2)	C21—C20—H20B	110.7
C24—O8—C28	107.9 (3)	H20A—C20—H20B	108.8
C24—O8—Na1	97.9 (2)	O7—C21—C24	103.6 (3)
C28—O8—Na1	115.8 (2)	O7—C21—C20	104.9 (4)
C35—O9—C29	116.2 (3)	C24—C21—C20	116.8 (4)
C35—O9—Na1	99.4 (2)	O7—C21—C22	107.9 (4)
C29—O9—Na1	102.8 (2)	C24—C21—C22	111.8 (4)
C36—O10—Na1	113.5 (2)	C20—C21—C22	111.0 (4)
C36—O10—H10	99 (5)	C21—C22—C23	113.7 (5)
Na1—O10—H10	115 (5)	C21—C22—H22A	108.8
C35—O11—H11	109.5	C23—C22—H22A	108.8
O1—C1—O2	125.3 (4)	C21—C22—H22B	108.8
O1—C1—C2	117.2 (3)	C23—C22—H22B	108.8
O2—C1—C2	117.4 (3)	H22A—C22—H22B	107.7
C4—C2—C3	111.5 (3)	C22—C23—H23A	109.5
C4—C2—C1	110.7 (3)	C22—C23—H23B	109.5
C3—C2—C1	109.3 (3)	H23A—C23—H23B	109.5
C4—C2—H2	108.4	C22—C23—H23C	109.5
C3—C2—H2	108.4	H23A—C23—H23C	109.5
C1—C2—H2	108.4	H23B—C23—H23C	109.5
C2—C3—H3A	109.5	O8—C24—C21	110.7 (3)
C2—C3—H3B	109.5	O8—C24—C25	103.6 (4)
H3A—C3—H3B	109.5	C21—C24—C25	120.7 (4)
C2—C3—H3C	109.5	O8—C24—H24	107.0
H3A—C3—H3C	109.5	C21—C24—H24	107.0
H3B—C3—H3C	109.5	C25—C24—H24	107.0
O3—C4—C2	105.3 (3)	C26—C25—C24	115.7 (4)
O3—C4—C6	109.1 (3)	C26—C25—C27	111.2 (5)
C2—C4—C6	116.3 (3)	C24—C25—C27	98.5 (4)
O3—C4—H4	108.6	C26—C25—H25	110.3
C2—C4—H4	108.6	C24—C25—H25	110.3
C6—C4—H4	108.6	C27—C25—H25	110.3
O3—C5—H5A	109.5	C25—C26—H26A	109.5
O3—C5—H5B	109.5	C25—C26—H26B	109.5
H5A—C5—H5B	109.5	H26A—C26—H26B	109.5
O3—C5—H5C	109.5	C25—C26—H26C	109.5
H5A—C5—H5C	109.5	H26A—C26—H26C	109.5
H5B—C5—H5C	109.5	H26B—C26—H26C	109.5
C7—C6—C8	111.2 (3)	C28—C27—C25	103.5 (4)
C7—C6—C4	111.7 (3)	C28—C27—H27A	111.1
C8—C6—C4	114.5 (3)	C25—C27—H27A	111.1
C7—C6—H6	106.3	C28—C27—H27B	111.1
C8—C6—H6	106.3	C25—C27—H27B	111.1
C4—C6—H6	106.3	H27A—C27—H27B	109.0
C6—C7—H7A	109.5	O8—C28—C29	108.5 (3)
C6—C7—H7B	109.5	O8—C28—C27	105.6 (4)
H7A—C7—H7B	109.5	C29—C28—C27	115.4 (4)
C6—C7—H7C	109.5	O8—C28—H28	109.1
H7A—C7—H7C	109.5	C29—C28—H28	109.1
H7B—C7—H7C	109.5	C27—C28—H28	109.1
O4—C8—C6	104.1 (3)	O9—C29—C30	111.2 (3)
O4—C8—C9	108.9 (3)	O9—C29—C28	104.6 (3)
C6—C8—C9	115.9 (3)	C30—C29—C28	114.6 (3)
O4—C8—H8	109.2	O9—C29—H29	108.7
C6—C8—H8	109.2	C30—C29—H29	108.7
C9—C8—H8	109.2	C28—C29—H29	108.7
C11—C9—C8	109.1 (3)	C32—C30—C29	109.1 (3)
C11—C9—C10	110.0 (3)	C32—C30—C31	111.1 (4)
C8—C9—C10	113.9 (3)	C29—C30—C31	111.1 (3)
C11—C9—H9	107.9	C32—C30—H30	108.5
C8—C9—H9	107.9	C29—C30—H30	108.5
C10—C9—H9	107.9	C31—C30—H30	108.5
C9—C10—H10A	109.5	C30—C31—H31A	109.5
C9—C10—H10B	109.5	C30—C31—H31B	109.5
H10A—C10—H10B	109.5	H31A—C31—H31B	109.5
C9—C10—H10C	109.5	C30—C31—H31C	109.5
H10A—C10—H10C	109.5	H31A—C31—H31C	109.5
H10B—C10—H10C	109.5	H31B—C31—H31C	109.5
O5—C11—C12	106.7 (3)	C33—C32—C30	112.0 (4)
O5—C11—C9	112.3 (3)	C33—C32—H32A	109.2
C12—C11—C9	111.1 (3)	C30—C32—H32A	109.2
O5—C11—H11A	108.9	C33—C32—H32B	109.2
C12—C11—H11A	108.9	C30—C32—H32B	109.2
C9—C11—H11A	108.9	H32A—C32—H32B	107.9
C13—C12—C11	113.8 (3)	C32—C33—C34	112.4 (4)
C13—C12—H12A	108.8	C32—C33—C35	108.6 (3)
C11—C12—H12A	108.8	C34—C33—C35	112.6 (3)
C13—C12—H12B	108.8	C32—C33—H33	107.7
C11—C12—H12B	108.8	C34—C33—H33	107.7
H12A—C12—H12B	107.7	C35—C33—H33	107.7
O4—C13—O6	109.9 (3)	C33—C34—H34A	109.5
O4—C13—C12	111.7 (3)	C33—C34—H34B	109.5
O6—C13—C12	108.6 (3)	H34A—C34—H34B	109.5
O4—C13—C14	107.3 (3)	C33—C34—H34C	109.5
O6—C13—C14	104.3 (3)	H34A—C34—H34C	109.5
C12—C13—C14	114.7 (3)	H34B—C34—H34C	109.5
C15—C14—C13	103.3 (3)	O11—C35—O9	108.7 (3)
C15—C14—H14A	111.1	O11—C35—C36	111.3 (3)
C13—C14—H14A	111.1	O9—C35—C36	104.0 (3)
C15—C14—H14B	111.1	O11—C35—C33	109.8 (3)
C13—C14—H14B	111.1	O9—C35—C33	108.8 (3)
H14A—C14—H14B	109.1	C36—C35—C33	114.0 (3)
C14—C15—C16	105.3 (4)	O10—C36—C35	110.5 (3)
C14—C15—H15A	110.7	O10—C36—H36A	109.6
C16—C15—H15A	110.7	C35—C36—H36A	109.6
C14—C15—H15B	110.7	O10—C36—H36B	109.6
C16—C15—H15B	110.7	C35—C36—H36B	109.6
H15A—C15—H15B	108.8	H36A—C36—H36B	108.1
O6—C16—C17	109.0 (3)	H12D—O12—H12E	110 (3)
O6—C16—C15	104.8 (3)	H13A—O13—H13B	108 (2)
C17—C16—C15	113.2 (4)
O6—Na1—O5—C11	1.9 (4)	O6—C13—C14—C15	32.8 (4)
O10—Na1—O5—C11	−106.5 (4)	C12—C13—C14—C15	151.5 (4)
O9—Na1—O5—C11	−179.5 (3)	C13—C14—C15—C16	−29.6 (5)
O8—Na1—O5—C11	113.4 (4)	C13—O6—C16—C17	−115.7 (4)
O7—Na1—O5—C11	37.5 (4)	Na1—O6—C16—C17	66.0 (4)
O5—Na1—O6—C13	0.7 (3)	C13—O6—C16—C15	5.7 (4)
O10—Na1—O6—C13	115.1 (3)	Na1—O6—C16—C15	−172.5 (3)
O8—Na1—O6—C13	−99.2 (3)	C13—O6—C16—C18	124.7 (3)
O7—Na1—O6—C13	−153.7 (3)	Na1—O6—C16—C18	−53.6 (4)
O5—Na1—O6—C16	178.4 (3)	C14—C15—C16—O6	15.4 (4)
O10—Na1—O6—C16	−67.2 (3)	C14—C15—C16—C17	134.1 (4)
O8—Na1—O6—C16	78.5 (3)	C14—C15—C16—C18	−99.5 (4)
O7—Na1—O6—C16	24.0 (2)	C21—O7—C18—C19	−39.1 (4)
O5—Na1—O7—C18	−27.0 (3)	Na1—O7—C18—C19	85.7 (3)
O6—Na1—O7—C18	10.3 (3)	C21—O7—C18—C16	−164.9 (3)
O10—Na1—O7—C18	121.2 (3)	Na1—O7—C18—C16	−40.1 (4)
O9—Na1—O7—C18	−168.0 (3)	O6—C16—C18—O7	60.7 (4)
O8—Na1—O7—C18	−117.2 (3)	C17—C16—C18—O7	−57.7 (4)
O5—Na1—O7—C21	95.5 (3)	C15—C16—C18—O7	174.8 (4)
O6—Na1—O7—C21	132.7 (3)	O6—C16—C18—C19	−55.8 (5)
O10—Na1—O7—C21	−116.4 (3)	C17—C16—C18—C19	−174.2 (4)
O9—Na1—O7—C21	−45.6 (3)	C15—C16—C18—C19	58.2 (5)
O8—Na1—O7—C21	5.2 (3)	O7—C18—C19—C20	33.0 (5)
O5—Na1—O8—C24	−171.1 (2)	C16—C18—C19—C20	151.4 (4)
O6—Na1—O8—C24	−90.4 (2)	C18—C19—C20—C21	−15.8 (5)
O10—Na1—O8—C24	51.4 (3)	C18—O7—C21—C24	151.6 (3)
O9—Na1—O8—C24	90.5 (2)	Na1—O7—C21—C24	26.6 (4)
O7—Na1—O8—C24	−36.6 (2)	C18—O7—C21—C20	28.7 (4)
O5—Na1—O8—C28	74.6 (3)	Na1—O7—C21—C20	−96.3 (3)
O6—Na1—O8—C28	155.2 (2)	C18—O7—C21—C22	−89.8 (4)
O10—Na1—O8—C28	−62.9 (3)	Na1—O7—C21—C22	145.3 (3)
O9—Na1—O8—C28	−23.8 (2)	C19—C20—C21—O7	−6.7 (5)
O7—Na1—O8—C28	−151.0 (3)	C19—C20—C21—C24	−120.8 (4)
O5—Na1—O9—C35	69.6 (2)	C19—C20—C21—C22	109.6 (5)
O10—Na1—O9—C35	−45.2 (2)	O7—C21—C22—C23	−52.7 (7)
O8—Na1—O9—C35	169.5 (2)	C24—C21—C22—C23	60.6 (7)
O7—Na1—O9—C35	−137.0 (2)	C20—C21—C22—C23	−167.1 (6)
O5—Na1—O9—C29	−50.2 (2)	C28—O8—C24—C21	−167.0 (3)
O10—Na1—O9—C29	−164.9 (3)	Na1—O8—C24—C21	72.5 (3)
O8—Na1—O9—C29	49.7 (2)	C28—O8—C24—C25	−36.3 (4)
O7—Na1—O9—C29	103.2 (2)	Na1—O8—C24—C25	−156.8 (3)
O5—Na1—O10—C36	−79.4 (3)	O7—C21—C24—O8	−70.6 (4)
O6—Na1—O10—C36	−164.7 (3)	C20—C21—C24—O8	44.2 (5)
O9—Na1—O10—C36	15.3 (3)	C22—C21—C24—O8	173.5 (4)
O8—Na1—O10—C36	53.0 (3)	O7—C21—C24—C25	168.3 (4)
O7—Na1—O10—C36	124.9 (3)	C20—C21—C24—C25	−76.9 (5)
O1—C1—C2—C4	−121.7 (4)	C22—C21—C24—C25	52.4 (6)
O2—C1—C2—C4	58.6 (4)	O8—C24—C25—C26	−73.4 (5)
O1—C1—C2—C3	115.1 (4)	C21—C24—C25—C26	51.1 (6)
O2—C1—C2—C3	−64.6 (4)	O8—C24—C25—C27	45.2 (4)
C5—O3—C4—C2	154.0 (3)	C21—C24—C25—C27	169.7 (4)
C5—O3—C4—C6	−80.5 (4)	C26—C25—C27—C28	84.3 (4)
C3—C2—C4—O3	−54.6 (4)	C24—C25—C27—C28	−37.6 (4)
C1—C2—C4—O3	−176.6 (3)	C24—O8—C28—C29	−113.1 (3)
C3—C2—C4—C6	−175.5 (3)	Na1—O8—C28—C29	−4.7 (4)
C1—C2—C4—C6	62.5 (4)	C24—O8—C28—C27	11.1 (4)
O3—C4—C6—C7	−77.3 (4)	Na1—O8—C28—C27	119.6 (3)
C2—C4—C6—C7	41.5 (4)	C25—C27—C28—O8	17.9 (4)
O3—C4—C6—C8	155.3 (3)	C25—C27—C28—C29	137.7 (4)
C2—C4—C6—C8	−85.9 (4)	C35—O9—C29—C30	57.0 (4)
C13—O4—C8—C6	−173.4 (3)	Na1—O9—C29—C30	164.4 (3)
C13—O4—C8—C9	62.3 (4)	C35—O9—C29—C28	−178.7 (3)
C7—C6—C8—O4	55.2 (4)	Na1—O9—C29—C28	−71.3 (3)
C4—C6—C8—O4	−177.2 (3)	O8—C28—C29—O9	50.4 (4)
C7—C6—C8—C9	174.7 (3)	C27—C28—C29—O9	−67.8 (4)
C4—C6—C8—C9	−57.6 (4)	O8—C28—C29—C30	172.5 (3)
O4—C8—C9—C11	−59.1 (4)	C27—C28—C29—C30	54.4 (5)
C6—C8—C9—C11	−176.0 (3)	O9—C29—C30—C32	−51.1 (5)
O4—C8—C9—C10	64.2 (4)	C28—C29—C30—C32	−169.6 (3)
C6—C8—C9—C10	−52.7 (4)	O9—C29—C30—C31	−173.9 (4)
Na1—O5—C11—C12	−34.6 (5)	C28—C29—C30—C31	67.7 (5)
Na1—O5—C11—C9	87.4 (4)	C29—C30—C32—C33	53.9 (4)
C8—C9—C11—O5	−66.7 (4)	C31—C30—C32—C33	176.7 (3)
C10—C9—C11—O5	167.7 (3)	C30—C32—C33—C34	177.4 (4)
C8—C9—C11—C12	52.7 (4)	C30—C32—C33—C35	−57.4 (4)
C10—C9—C11—C12	−72.8 (4)	C29—O9—C35—O11	59.9 (4)
O5—C11—C12—C13	75.5 (4)	Na1—O9—C35—O11	−49.4 (3)
C9—C11—C12—C13	−47.2 (5)	C29—O9—C35—C36	178.6 (3)
C8—O4—C13—O6	65.1 (4)	Na1—O9—C35—C36	69.3 (3)
C8—O4—C13—C12	−55.6 (4)	C29—O9—C35—C33	−59.5 (4)
C8—O4—C13—C14	177.8 (3)	Na1—O9—C35—C33	−168.9 (3)
C16—O6—C13—O4	90.2 (3)	C32—C33—C35—O11	−61.5 (4)
Na1—O6—C13—O4	−92.0 (4)	C34—C33—C35—O11	63.6 (4)
C16—O6—C13—C12	−147.3 (3)	C32—C33—C35—O9	57.3 (4)
Na1—O6—C13—C12	30.5 (4)	C34—C33—C35—O9	−177.6 (3)
C16—O6—C13—C14	−24.5 (4)	C32—C33—C35—C36	172.8 (4)
Na1—O6—C13—C14	153.3 (3)	C34—C33—C35—C36	−62.1 (5)
C11—C12—C13—O4	47.2 (5)	Na1—O10—C36—C35	16.2 (4)
C11—C12—C13—O6	−74.2 (4)	O11—C35—C36—O10	56.4 (5)
C11—C12—C13—C14	169.5 (4)	O9—C35—C36—O10	−60.4 (4)
O4—C13—C14—C15	−83.7 (4)	C33—C35—C36—O10	−178.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O13	0.84 (2)	2.04 (3)	2.810 (7)	152 (5)
O10—H10···O1	0.84 (2)	1.81 (2)	2.643 (4)	170 (8)
O11—H11···O2	0.84	1.88	2.665 (4)	156
O12—H12E···O2	0.90 (2)	1.90 (2)	2.791 (4)	174 (5)
O12—H12D···O3^i	0.91 (2)	2.05 (3)	2.907 (4)	157 (5)
O13—H13B···O11	0.99 (1)	2.04 (5)	2.882 (10)	142 (6)
O13—H13A···O12	0.99 (1)	1.96 (4)	2.769 (8)	137 (5)

Symmetry code: (i) x+1/2, −y+3/2, −z+1.