The methanol sesquisolvate of sodium naproxen

Kriegner, H.; Weil, M.; Jones, M.J.

doi:10.1107/S2056989018014652

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Volume 74| Part 11| November 2018| Pages 1624-1627

https://doi.org/10.1107/S2056989018014652

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The methanol sesquisolvate of sodium naproxen

Helene Kriegner,^a Matthias Weil ^a ^* and Matthew J. Jones ^b

^aInstitute for Chemical Technologies and Analytics, Division of Structural Chemistry, TU Wien, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria, and ^bPatheon Austria GmbH & Co KG, St.-Peter-Strasse 25, A-4020 Linz, Austria
^*Correspondence e-mail: Matthias.Weil@tuwien.ac.at

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 9 October 2018; accepted 16 October 2018; online 19 October 2018)

The asymmetric unit of the methanol solvate of sodium naproxen, systematic name: sodium (2S)-2-(6-methoxynaphthalen-2-yl)propanoate methanol sesquisolvate, Na⁺·C₁₄H₁₃O₃⁻·1.5CH₃OH, comprises two formula units of the molecular salt and three methanol molecules. One of the sodium cations exhibits a coordination number of six and is bonded to three carboxylate O atoms and three methanol OH groups whereas the second sodium cation has a coordination number of seven, defined by five carboxylate O atoms and two methanol OH groups. Both coordination polyhedra around the sodium cations are considerably distorted. The two types of cations are bridged into polymeric chains extending parallel to [010]. This arrangement is stabilized by intrachain O—H⋯O hydrogen bonds between methanol ligands as donor and carboxylate O atoms as acceptor groups. The hydrophobic 6-methoxynaphthyl moieties flank the hydrophilic sodium oxygen chains into ribbons parallel to [010]. There are no noticeable intermolecular interactions between these ribbons. One of the 6-methoxynaphthyl moieties is disordered over two sets of sites in a 0.723 (3):0.277 (3) ratio.

Keywords: crystal structure; solvatomorphism; naproxen; methanol solvate; disorder.

CCDC reference: 1873620

1. Chemical context

Naproxen, or (S)-2-(6-methoxynaphthalen-2-yl)propanoic acid, and in particular its better soluble sodium salt are non-steroidal anti-inflammatory drugs with pain-relieving and antipyretic properties. For a recent project on the crystallization of active pharmaceutical ingredients (APIs; Kovačič et al., 2012 ), we used sodium naproxen as a model substance. During these investigations, we obtained the methanol sesquisolvate as a solvatomorph of sodium naproxen, [Na(C₁₄H₁₃O₃)]·1.5CH₃OH. Although a preliminary structure model of this compound has been reported as part of a PhD thesis (Chavez, 2009 ), it was never published or deposited in the Cambridge Structural Database (Groom et al., 2016 ). We report here the precise crystal structure determination of [Na(C₁₄H₁₃O₃)]·1.5CH₃OH, (I), including disorder of one 6-methoxynaphthyl moiety that was not modelled in the preliminary study (Chavez, 2009).

2. Structural commentary

The asymmetric unit of (I) is displayed in Fig. 1 and comprises two Na⁺ cations, two naproxate anions (one of which shows disorder of the 6-methoxynaphthyl moiety) and three methanol molecules (Z′ = 2). Na1 is bound to six oxygen atoms, three of them originating from methanol OH groups and three from monodentate carboxylate groups (O2; O5; O4ⁱ; for symmetry codes, see: Table 1). The Na1—O bond lengths are not uniformly distributed, revealing a distorted [5 + 1] coordination with five shorter bonds between 2.2355 (14) and 2.4403 (14) Å and one significantly longer bond of 2.856 (2) Å to the OH group of a methanol molecule. In comparison, the coordination sphere of Na2 is enlarged to seven coordination partners, two of them from methanol OH groups, four from two chelating carboxylate groups (O1ⁱ,O2ⁱ; O4ⁱ,O5ⁱ) and one from a monodentate carboxylate group (O5). The Na2—O distances are somewhat more evenly distributed and range from 2.3418 (13) to 2.5983 (14) Å. Nevertheless, the resulting coordination polyhedron around Na2 is likewise distorted. Details of the Na—O coordination spheres are depicted in Fig. 2. The bond-valence sums (Brown, 2002 ) of 1.24 and 1.17 valence units for Na1 and Na2, respectively, are higher than expected and point to some strain in the structure.

Table 1
Selected bond lengths (Å)

Na1—O2	2.2355 (14)	Na2—O1S	2.3667 (15)
Na1—O3S	2.3003 (15)	Na2—O4ⁱ	2.4635 (13)
Na1—O5	2.3604 (13)	Na2—O2S	2.4748 (14)
Na1—O2S	2.3838 (14)	Na2—O1ⁱ	2.5394 (14)
Na1—O4ⁱ	2.4403 (14)	Na2—O2ⁱ	2.5459 (15)
Na1—O1Sⁱⁱ	2.856 (2)	Na2—O5ⁱ	2.5983 (14)
Na2—O5	2.3418 (13)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Figure 1
The asymmetric unit of (I)

with displacement ellipsoids drawn at the 30% probability level. The minor disordered part B of one 6-methoxynaphthyl moiety is displayed with open bonds and without labelling of atoms.

Figure 2
Part of the crystal structure of (I)

emphasizing the coordination environments of the two Na⁺ cations. Displacement ellipsoids are drawn at the 50% probability level. Symmetry codes refer to Table 1

The two sodium cations are bridged by the O1S and O2S methanol OH groups and by carboxylate atoms O2, O4 and O5 into zigzag chains extending parallel to [010]. The third methanol molecule is terminally bound to Na1. The hydrophobic 6-methoxynaphthyl moieties flank the hydrophilic [Na—O]_n chains, leading to the formation of ribbons along the chain direction (Fig. 3). The methoxy groups attached to the naphthyl rings are twisted slightly out of the aromatic plane, with dihedral angles of 6.42 (18)° for ring (C1–C10) and methoxy group O3–C14, and 5.2 (3)° for ring (C15A–C24A) and methoxy group O6A–C28A.

Figure 3
The crystal structure of (I)

in a projection along [001]. O—H⋯O hydrogen bonds within a ribbon are displayed in blue on the right hand side. For clarity, only the major part A of the disordered 6-methoxynaphthyl moiety is shown.

3. Supramolecular features

Intrachain O—H⋯O hydrogen bonding interactions of medium strength [Table 2, Fig. 3(right)] between methanol molecules and carboxylate O atoms stabilize the arrangement within the ribbons. Oxygen atom O1, which is not a bridging atom in the [Na—O]_n chain and which has a comparatively long Na—O bond, is the acceptor of two hydrogen bonds.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1S—H1S⋯O4ⁱⁱⁱ	0.84 (2)	1.90 (2)	2.6756 (18)	153 (3)
O2S—H2S⋯O1ⁱⁱⁱ	0.83 (2)	2.06 (2)	2.8331 (18)	156 (3)
O3S—H3S⋯O1ⁱⁱⁱ	0.79 (2)	1.94 (2)	2.7226 (19)	172 (3)
Symmetry code: (iii) x, y-1, z.

There are no notable intermolecular interactions between adjacent ribbons involving the outer hydrophobic parts. It seems that cohesion of the ribbons is dominated by van der Waals forces only.

4. Database survey

The crystal structure of naproxen, i.e. the free acid (±)2-(6-methoxy-2-naphthyl)propionic acid, was reported by Ravikumar et al. (1985 ). A search in the Cambridge Structural Database (CSD version 5.39, November 2017, update 3, May 2018; Groom et al., 2016) for the sodium salt and its hydrates revealed six entries: anhydrous sodium naproxen, [Na(C₁₄H₁₃O₃)] (Kim et al., 2004 ), sodium naproxen monohydrate [Na(C₁₄H₁₃O₃)]·H₂O (Kim et al., 1990 ), two forms of sodium naproxen dihydrate [Na(C₁₄H₁₃O₃)]·2H₂O (Bond et al., 2014 ), and sodium naproxen heminonahydrate [Na(C₁₄H₁₃O₃)]·4.5H₂O (Burgess et al., 2012 ) that was subsequently reinterpreted as a disordered tetrahydrate [Na(C₁₄H₁₃O₃)]·4H₂O (Bond et al., 2013 ). The structural motif of ribbons formed between sodium cations and oxygen atoms is likewise found in all anhydrous and hydrous sodium naproxen structures.

Only one methanol solvate of naproxen is deposited in the CSD. However, this is an Na salt of naproxen with an additional free acid molecule, viz. sodium hydrogen bis(naproxate) methanol disolvate, [Na(C₁₄H₁₃O₃)(C₁₄H₁₄O₃)]·2CH₃OH (Perumalla & Sun, 2012 ). A homologous series of alcohol solvates of sodium naproxen obtained as polycrystalline powders and without structure determinations was reported by Chavez et al. (2010 ). During these investigations, another methanol solvate of sodium naproxen was reported with only one methanol molecule per formula unit (Chavez, 2009; Burgess et al., 2012).

5. Synthesis and crystallization

Crystals of sodium naproxen methanol sesquisolvate were grown by slow crystallization in methanol. Polycrystalline anhydrous sodium naproxen was dissolved in methanol to yield a solution 20% in weight of the salt. 0.5 ml of this solution were heated to 338 K and slowly cooled down to room temperature (298 K) over the course of 130 min (cooling rate 0.3 K min⁻¹). Colourless parallelepipeds with edge lengths of up to 1 cm were obtained. A suitable fragment was broken from a larger specimen for the X-ray diffraction experiment.

6. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 3. The structure model obtained with SHELXT (Sheldrick, 2015a ) was very similar to the preliminary model of Chavez (2009) from 173 K data using Cu K_α radiation. After placing all atoms with full occupancy in the asymmetric unit, elongated displacement parameters of atoms of one of the 6-methoxynaphthyl moieties and conspicuous electron density peaks in the vicinity of these atoms were found. This model converged with R[F² > 2σ(F²)] = 0.08 and wR(F²) = 0.23. Consideration of disorder over two sets of sites for this fragment led to more spherical atoms and much better reliability factors (Table 3). The refined occupancy ratio of the two disordered parts is 0.723 (3):0.277 (3) for major part A: minor part B. The positions of C-bound H atoms were calculated and refined using a riding model, with C—H = 0.93–0.98 Å, and with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C) for methyl H atoms. H atoms bound to methanol O atoms were clearly discernible from difference maps. They were refined with distance restraints of 0.85±2 Å and free U_iso(H) values. The absolute structure was determined on the basis of the current data set (Table 3), revealing that the usual (S) enantiomer is present.

Table 3
Experimental details

Crystal data
Chemical formula	Na⁺·C₁₄H₁₃O₃⁻·1.5CH₃OH
M_r	300.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	12.6776 (9), 7.9675 (6), 15.1932 (11)
β (°)	95.7559 (19)
V (Å³)	1526.91 (19)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.12
Crystal size (mm)	0.45 × 0.45 × 0.35

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.675, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	32667, 11521, 10262
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.767

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.105, 1.02
No. of reflections	11521
No. of parameters	508
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.24
Absolute structure	Flack x determined using 4468 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.07 (8)
Computer programs: APEX3 and SAINT (Bruker, 2017 ), SHELXT (Sheldrick, 2015a), SHELXL2017 (Sheldrick, 2015b ), Mercury (Macrae et al., 2008 ), ATOMS (Dowty, 2006 ) and XP in SHELXTL (Sheldrick, 2008 ), publCIF (Westrip, 2010 ).

Reflections (100) and (001) were obstructed by the beam stop and were omitted from the refinement.

Lattice parameters refined from single-crystal room temperature X-ray data are a = 12.8458 (9), b = 8.0235 (6), c = 15.3012 (11) Å, β = 94.898 (2)°.

Supporting information

CCDC reference: 1873620

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989018014652/rz5244sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018014652/rz5244Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008), ATOMS (Dowty, 2006) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Sodium (2S)-2-(6-methoxynaphthalen-2-yl)propanoate methanol sesquisolvate top

Crystal data top

Na⁺·C₁₄H₁₃O₃⁻·1.5CH₄O	F(000) = 636
M_r = 300.30	D_x = 1.306 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 12.6776 (9) Å	Cell parameters from 9943 reflections
b = 7.9675 (6) Å	θ = 2.5–38.0°
c = 15.1932 (11) Å	µ = 0.12 mm⁻¹
β = 95.7559 (19)°	T = 100 K
V = 1526.91 (19) Å³	Block, colourless
Z = 4	0.45 × 0.45 × 0.35 mm

Data collection top

Bruker APEXII CCD diffractometer	10262 reflections with I > 2σ(I)
ω scans	R_int = 0.029
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 33.0°, θ_min = 2.2°
T_min = 0.675, T_max = 0.747	h = −16→19
32667 measured reflections	k = −12→12
11521 independent reflections	l = −23→22

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0585P)² + 0.2474P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.105	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.43 e Å⁻³
11521 reflections	Δρ_min = −0.24 e Å⁻³
508 parameters	Absolute structure: Flack x determined using 4468 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
4 restraints	Absolute structure parameter: −0.07 (8)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Na1	0.35919 (5)	0.41121 (8)	0.55421 (5)	0.01949 (13)
Na2	0.53085 (5)	0.27034 (8)	0.43935 (4)	0.01651 (12)
O1	0.30172 (10)	0.93243 (15)	0.58392 (9)	0.0234 (2)
O2	0.27973 (11)	0.66163 (15)	0.55460 (10)	0.0259 (3)
O3	0.09118 (12)	0.70972 (19)	1.09131 (8)	0.0282 (3)
O4	0.46523 (10)	0.79820 (14)	0.39887 (8)	0.0209 (2)
O5	0.44988 (10)	0.53419 (14)	0.44218 (8)	0.0194 (2)
C1	0.09928 (11)	0.80698 (17)	0.67179 (9)	0.0141 (2)
C2	0.16031 (12)	0.71291 (19)	0.73342 (10)	0.0167 (2)
H2	0.218745	0.651509	0.715525	0.020*
C3	0.13817 (12)	0.7053 (2)	0.82309 (10)	0.0177 (3)
C4	0.20276 (15)	0.6122 (2)	0.88774 (11)	0.0245 (3)
H4	0.259778	0.546767	0.870353	0.029*
C5	0.18346 (15)	0.6161 (2)	0.97496 (12)	0.0255 (3)
H5	0.227230	0.553456	1.017487	0.031*
C6	0.09883 (15)	0.7127 (2)	1.00203 (11)	0.0228 (3)
C7	0.03229 (13)	0.7995 (2)	0.94124 (10)	0.0205 (3)
H7	−0.025886	0.860850	0.959611	0.025*
C8	0.05126 (12)	0.79659 (19)	0.85034 (10)	0.0173 (3)
C9	−0.01335 (12)	0.8878 (2)	0.78550 (10)	0.0187 (3)
H9	−0.073439	0.946900	0.801972	0.022*
C10	0.00991 (12)	0.89198 (19)	0.69887 (10)	0.0171 (3)
H10	−0.034925	0.953119	0.656440	0.020*
C11	0.12458 (12)	0.82248 (19)	0.57623 (10)	0.0164 (2)
H11	0.104366	0.938450	0.555788	0.020*
C12	0.24397 (12)	0.80296 (18)	0.57028 (10)	0.0161 (2)
C13	0.05919 (15)	0.6995 (3)	0.51580 (12)	0.0306 (4)
H13A	0.077854	0.584172	0.533647	0.046*
H13B	0.074224	0.717156	0.454462	0.046*
H13C	−0.016427	0.718215	0.520568	0.046*
C14	0.0128 (2)	0.8144 (3)	1.12363 (13)	0.0371 (5)
H14A	0.025640	0.931340	1.107814	0.056*
H14B	0.016201	0.804060	1.188131	0.056*
H14C	−0.057606	0.779923	1.097220	0.056*
C27	0.43419 (12)	0.64886 (19)	0.38570 (10)	0.0168 (3)
C26	0.2643 (2)	0.6973 (4)	0.29275 (16)	0.0477 (6)
H26A	0.275881	0.818801	0.290702	0.072*
H26B	0.228868	0.669292	0.345285	0.072*
H26C	0.219732	0.661993	0.239531	0.072*
C25	0.37115 (15)	0.6064 (2)	0.29702 (11)	0.0256 (3)
H25A	0.357320	0.482859	0.295488	0.031*	0.723 (3)
H25B	0.352875	0.484963	0.302090	0.031*	0.277 (3)
C15A	0.4275 (3)	0.6512 (5)	0.2181 (2)	0.0216 (6)	0.723 (3)
C16A	0.5293 (2)	0.5923 (4)	0.21714 (16)	0.0245 (5)	0.723 (3)
H16A	0.561067	0.532294	0.266975	0.029*	0.723 (3)
C17A	0.5886 (2)	0.6187 (3)	0.14351 (18)	0.0227 (5)	0.723 (3)
C18A	0.6929 (2)	0.5558 (4)	0.14182 (16)	0.0274 (5)	0.723 (3)
H18A	0.725846	0.496607	0.191447	0.033*	0.723 (3)
C19A	0.7463 (2)	0.5801 (4)	0.06897 (16)	0.0265 (5)	0.723 (3)
H19A	0.815841	0.535976	0.068427	0.032*	0.723 (3)
C20A	0.6998 (2)	0.6698 (4)	−0.00588 (19)	0.0205 (5)	0.723 (3)
C21A	0.59938 (19)	0.7341 (3)	−0.00630 (14)	0.0218 (5)	0.723 (3)
H21A	0.568545	0.795556	−0.055962	0.026*	0.723 (3)
C22A	0.5413 (3)	0.7079 (5)	0.0688 (2)	0.0212 (6)	0.723 (3)
C23A	0.43633 (19)	0.7676 (3)	0.07052 (14)	0.0231 (5)	0.723 (3)
H23A	0.403419	0.827833	0.021220	0.028*	0.723 (3)
C24A	0.3816 (2)	0.7395 (3)	0.14262 (16)	0.0241 (5)	0.723 (3)
H24A	0.311058	0.780256	0.141984	0.029*	0.723 (3)
C28A	0.7197 (2)	0.7553 (5)	−0.1545 (2)	0.0315 (6)	0.723 (3)
H28A	0.656366	0.692641	−0.177536	0.047*	0.723 (3)
H28B	0.772161	0.751836	−0.197667	0.047*	0.723 (3)
H28C	0.700449	0.872125	−0.143910	0.047*	0.723 (3)
O6A	0.76404 (16)	0.6807 (3)	−0.07288 (12)	0.0237 (4)	0.723 (3)
O1S	0.50266 (14)	0.08627 (18)	0.31699 (10)	0.0341 (3)
C1S	0.55409 (18)	0.0686 (3)	0.24025 (14)	0.0322 (4)
H1S1	0.587260	0.175409	0.226716	0.048*
H1S2	0.502388	0.036587	0.190801	0.048*
H1S3	0.608648	−0.018496	0.249473	0.048*
O2S	0.34838 (10)	0.17528 (15)	0.45724 (8)	0.0205 (2)
C2S	0.25390 (17)	0.1708 (3)	0.39960 (16)	0.0391 (5)
H2S1	0.195993	0.128143	0.431475	0.059*
H2S2	0.263523	0.096897	0.349473	0.059*
H2S3	0.236603	0.284294	0.377843	0.059*
O3S	0.24271 (15)	0.24954 (18)	0.62435 (13)	0.0412 (4)
C3S	0.16678 (18)	0.2742 (3)	0.68361 (15)	0.0337 (4)
H3S1	0.202144	0.285994	0.743672	0.051*
H3S2	0.118646	0.177752	0.681302	0.051*
H3S3	0.126265	0.376335	0.667452	0.051*
O6B	0.7222 (7)	0.7340 (10)	−0.1082 (7)	0.050 (2)	0.277 (3)
C15B	0.4588 (7)	0.6105 (10)	0.2265 (5)	0.0158 (13)	0.277 (3)
C24B	0.5534 (7)	0.5183 (10)	0.2415 (5)	0.0313 (16)	0.277 (3)
H24B	0.566878	0.454601	0.294247	0.038*	0.277 (3)
C23B	0.6268 (7)	0.5193 (10)	0.1806 (6)	0.0365 (18)	0.277 (3)
H23B	0.689893	0.454986	0.191046	0.044*	0.277 (3)
C22B	0.6085 (6)	0.6161 (9)	0.1022 (5)	0.0292 (15)	0.277 (3)
C21B	0.6837 (7)	0.6204 (10)	0.0362 (6)	0.0324 (17)	0.277 (3)
H21B	0.747181	0.556454	0.043704	0.039*	0.277 (3)
C20B	0.6611 (8)	0.7178 (12)	−0.0363 (6)	0.0355 (19)	0.277 (3)
C19B	0.5698 (8)	0.8163 (13)	−0.0498 (5)	0.045 (2)	0.277 (3)
H19B	0.558921	0.887368	−0.100039	0.054*	0.277 (3)
C18B	0.4966 (7)	0.8096 (12)	0.0097 (5)	0.0380 (18)	0.277 (3)
H18B	0.432892	0.872406	−0.001075	0.046*	0.277 (3)
C16B	0.4398 (6)	0.7027 (8)	0.1519 (4)	0.0204 (11)	0.277 (3)
H16B	0.375346	0.763864	0.142336	0.024*	0.277 (3)
C17B	0.5134 (9)	0.7109 (14)	0.0874 (7)	0.027 (2)	0.277 (3)
C28B	0.7973 (8)	0.6136 (14)	−0.1092 (8)	0.049 (2)	0.277 (3)
H28D	0.854049	0.635146	−0.061943	0.073*	0.277 (3)
H28E	0.826577	0.614705	−0.166515	0.073*	0.277 (3)
H28F	0.765540	0.503621	−0.099974	0.073*	0.277 (3)
H3S	0.256 (3)	0.155 (3)	0.615 (2)	0.049 (9)*
H1S	0.478 (2)	−0.009 (3)	0.3271 (18)	0.033 (7)*
H2S	0.350 (2)	0.090 (3)	0.4883 (18)	0.039 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0218 (3)	0.0118 (3)	0.0264 (3)	0.0010 (2)	0.0102 (2)	0.0011 (2)
Na2	0.0174 (3)	0.0133 (3)	0.0193 (3)	0.0021 (2)	0.0045 (2)	−0.0010 (2)
O1	0.0205 (5)	0.0154 (5)	0.0356 (7)	−0.0030 (4)	0.0100 (5)	0.0017 (4)
O2	0.0260 (6)	0.0152 (5)	0.0384 (7)	0.0048 (4)	0.0118 (5)	−0.0042 (5)
O3	0.0387 (7)	0.0308 (6)	0.0159 (5)	0.0053 (6)	0.0077 (5)	0.0033 (5)
O4	0.0310 (6)	0.0131 (4)	0.0182 (5)	−0.0021 (4)	0.0003 (4)	0.0015 (4)
O5	0.0235 (5)	0.0130 (4)	0.0231 (5)	0.0036 (4)	0.0089 (4)	0.0029 (4)
C1	0.0133 (6)	0.0129 (5)	0.0164 (6)	−0.0020 (4)	0.0033 (4)	−0.0023 (5)
C2	0.0167 (6)	0.0164 (6)	0.0173 (6)	0.0027 (5)	0.0033 (5)	−0.0008 (5)
C3	0.0188 (6)	0.0177 (6)	0.0168 (6)	0.0021 (5)	0.0028 (5)	0.0000 (5)
C4	0.0274 (8)	0.0264 (8)	0.0201 (7)	0.0093 (6)	0.0042 (6)	0.0024 (6)
C5	0.0299 (9)	0.0273 (8)	0.0195 (7)	0.0075 (7)	0.0030 (6)	0.0048 (6)
C6	0.0290 (8)	0.0232 (7)	0.0169 (6)	0.0001 (6)	0.0053 (6)	0.0010 (6)
C7	0.0231 (7)	0.0215 (7)	0.0177 (6)	0.0012 (5)	0.0062 (5)	−0.0010 (5)
C8	0.0184 (6)	0.0174 (6)	0.0166 (6)	−0.0002 (5)	0.0042 (5)	−0.0015 (5)
C9	0.0176 (6)	0.0201 (6)	0.0189 (6)	0.0026 (5)	0.0045 (5)	−0.0015 (5)
C10	0.0148 (6)	0.0184 (6)	0.0180 (6)	0.0006 (5)	0.0019 (5)	−0.0010 (5)
C11	0.0154 (6)	0.0184 (6)	0.0156 (6)	0.0014 (5)	0.0028 (5)	−0.0012 (5)
C12	0.0177 (6)	0.0145 (6)	0.0170 (6)	0.0016 (5)	0.0061 (5)	0.0011 (5)
C13	0.0248 (8)	0.0434 (10)	0.0236 (8)	−0.0100 (8)	0.0023 (6)	−0.0124 (7)
C14	0.0542 (13)	0.0394 (11)	0.0200 (8)	0.0117 (10)	0.0146 (8)	0.0036 (7)
C27	0.0203 (7)	0.0154 (6)	0.0156 (6)	0.0000 (5)	0.0053 (5)	−0.0014 (5)
C26	0.0367 (12)	0.0679 (17)	0.0352 (11)	0.0031 (12)	−0.0127 (9)	−0.0064 (11)
C25	0.0326 (9)	0.0282 (8)	0.0162 (7)	−0.0105 (7)	0.0036 (6)	−0.0049 (6)
C15A	0.0222 (16)	0.0255 (15)	0.0171 (11)	0.0012 (11)	0.0022 (10)	−0.0058 (11)
C16A	0.0302 (14)	0.0296 (13)	0.0134 (9)	0.0069 (10)	0.0002 (8)	−0.0005 (9)
C17A	0.0248 (11)	0.0295 (12)	0.0133 (10)	0.0081 (9)	−0.0008 (8)	0.0013 (8)
C18A	0.0286 (12)	0.0351 (13)	0.0178 (10)	0.0134 (10)	−0.0007 (8)	0.0027 (9)
C19A	0.0256 (12)	0.0337 (13)	0.0201 (10)	0.0108 (10)	0.0019 (9)	0.0002 (9)
C20A	0.0186 (11)	0.0251 (11)	0.0181 (11)	0.0053 (9)	0.0029 (9)	0.0005 (9)
C21A	0.0214 (10)	0.0288 (11)	0.0145 (9)	0.0053 (8)	−0.0010 (8)	−0.0008 (8)
C22A	0.0202 (15)	0.0287 (13)	0.0138 (14)	0.0072 (12)	−0.0026 (10)	−0.0001 (11)
C23A	0.0207 (10)	0.0309 (11)	0.0169 (9)	0.0081 (9)	−0.0025 (7)	0.0006 (8)
C24A	0.0232 (12)	0.0299 (12)	0.0187 (9)	0.0040 (10)	−0.0004 (8)	−0.0030 (8)
C28A	0.0321 (14)	0.0450 (16)	0.0169 (10)	−0.0077 (11)	−0.0006 (10)	0.0056 (11)
O6A	0.0191 (8)	0.0346 (10)	0.0178 (8)	0.0078 (7)	0.0040 (6)	0.0033 (7)
O1S	0.0552 (9)	0.0230 (6)	0.0274 (6)	−0.0187 (6)	0.0211 (6)	−0.0076 (5)
C1S	0.0385 (11)	0.0342 (10)	0.0251 (8)	−0.0100 (8)	0.0094 (7)	−0.0034 (7)
O2S	0.0200 (5)	0.0151 (5)	0.0267 (6)	−0.0003 (4)	0.0033 (4)	0.0007 (4)
C2S	0.0284 (10)	0.0434 (12)	0.0436 (11)	−0.0081 (9)	−0.0065 (8)	0.0083 (10)
O3S	0.0528 (10)	0.0150 (6)	0.0630 (11)	−0.0036 (6)	0.0417 (8)	−0.0020 (6)
C3S	0.0402 (10)	0.0241 (8)	0.0405 (10)	−0.0074 (8)	0.0214 (8)	−0.0073 (8)
O6B	0.051 (5)	0.037 (4)	0.064 (6)	−0.009 (3)	0.025 (4)	−0.009 (4)
C15B	0.018 (4)	0.014 (3)	0.016 (3)	0.003 (2)	0.006 (3)	−0.002 (2)
C24B	0.037 (4)	0.030 (3)	0.029 (3)	0.015 (3)	0.012 (3)	0.012 (3)
C23B	0.037 (4)	0.033 (4)	0.043 (4)	0.016 (3)	0.021 (3)	0.009 (3)
C22B	0.045 (4)	0.024 (3)	0.022 (3)	−0.011 (3)	0.017 (3)	−0.009 (2)
C21B	0.039 (4)	0.024 (3)	0.036 (4)	−0.007 (3)	0.015 (3)	−0.009 (3)
C20B	0.044 (5)	0.030 (4)	0.035 (4)	−0.016 (4)	0.016 (4)	−0.015 (3)
C19B	0.056 (5)	0.059 (6)	0.019 (3)	−0.025 (5)	0.001 (3)	0.006 (3)
C18B	0.044 (4)	0.050 (5)	0.020 (3)	−0.008 (4)	−0.001 (3)	0.012 (3)
C16B	0.023 (3)	0.019 (2)	0.018 (2)	0.003 (2)	−0.006 (2)	0.0044 (19)
C17B	0.040 (6)	0.022 (3)	0.021 (4)	−0.009 (4)	0.008 (3)	−0.004 (3)
C28B	0.031 (4)	0.051 (5)	0.063 (6)	−0.006 (4)	−0.002 (4)	0.013 (5)

Geometric parameters (Å, º) top

Na1—O2	2.2355 (14)	C16A—C17A	1.424 (4)
Na1—O3S	2.3003 (15)	C16A—H16A	0.9500
Na1—O5	2.3604 (13)	C17A—C18A	1.417 (4)
Na1—O2S	2.3838 (14)	C17A—C22A	1.420 (4)
Na1—O4ⁱ	2.4403 (14)	C18A—C19A	1.368 (4)
Na1—O1Sⁱⁱ	2.856 (2)	C18A—H18A	0.9500
Na2—O5	2.3418 (13)	C19A—C20A	1.420 (4)
Na2—O1S	2.3667 (15)	C19A—H19A	0.9500
Na2—O4ⁱ	2.4635 (13)	C20A—O6A	1.368 (3)
Na2—O2S	2.4748 (14)	C20A—C21A	1.372 (3)
Na2—O1ⁱ	2.5394 (14)	C21A—C22A	1.434 (4)
Na2—O2ⁱ	2.5459 (15)	C21A—H21A	0.9500
Na2—O5ⁱ	2.5983 (14)	C22A—C23A	1.416 (4)
O1—C12	1.2700 (19)	C23A—C24A	1.373 (3)
O2—C12	1.2457 (18)	C23A—H23A	0.9500
O3—C6	1.3698 (19)	C24A—H24A	0.9500
O3—C14	1.422 (3)	C28A—O6A	1.437 (3)
O4—C27	1.2629 (18)	C28A—H28A	0.9800
O5—C27	1.2555 (19)	C28A—H28B	0.9800
C1—C2	1.375 (2)	C28A—H28C	0.9800
C1—C10	1.416 (2)	O1S—C1S	1.399 (2)
C1—C11	1.523 (2)	O1S—H1S	0.84 (2)
C2—C3	1.420 (2)	C1S—H1S1	0.9800
C2—H2	0.9500	C1S—H1S2	0.9800
C3—C8	1.416 (2)	C1S—H1S3	0.9800
C3—C4	1.423 (2)	O2S—C2S	1.411 (2)
C4—C5	1.372 (2)	O2S—H2S	0.83 (2)
C4—H4	0.9500	C2S—H2S1	0.9800
C5—C6	1.415 (2)	C2S—H2S2	0.9800
C5—H5	0.9500	C2S—H2S3	0.9800
C6—C7	1.373 (2)	O3S—C3S	1.396 (2)
C7—C8	1.426 (2)	O3S—H3S	0.79 (2)
C7—H7	0.9500	C3S—H3S1	0.9800
C8—C9	1.417 (2)	C3S—H3S2	0.9800
C9—C10	1.378 (2)	C3S—H3S3	0.9800
C9—H9	0.9500	O6B—C28B	1.352 (13)
C10—H10	0.9500	O6B—C20B	1.408 (11)
C11—C13	1.529 (2)	C15B—C16B	1.352 (10)
C11—C12	1.533 (2)	C15B—C24B	1.405 (11)
C11—H11	1.0000	C24B—C23B	1.376 (10)
C13—H13A	0.9800	C24B—H24B	0.9500
C13—H13B	0.9800	C23B—C22B	1.417 (11)
C13—H13C	0.9800	C23B—H23B	0.9500
C14—H14A	0.9800	C22B—C17B	1.421 (15)
C14—H14B	0.9800	C22B—C21B	1.452 (11)
C14—H14C	0.9800	C21B—C20B	1.355 (14)
C27—C25	1.534 (2)	C21B—H21B	0.9500
C26—C25	1.532 (3)	C20B—C19B	1.396 (16)
C26—H26A	0.9800	C19B—C18B	1.359 (12)
C26—H26B	0.9800	C19B—H19B	0.9500
C26—H26C	0.9800	C18B—C17B	1.417 (13)
C25—C15A	1.499 (4)	C18B—H18B	0.9500
C25—C15B	1.620 (8)	C16B—C17B	1.421 (11)
C25—H25A	1.0000	C16B—H16B	0.9500
C25—H25B	1.0000	C28B—H28D	0.9800
C15A—C16A	1.375 (4)	C28B—H28E	0.9800
C15A—C24A	1.420 (4)	C28B—H28F	0.9800

O2—Na1—O3S	100.84 (6)	C26—C25—C15B	128.7 (3)
O2—Na1—O5	83.32 (5)	C27—C25—C15B	104.2 (3)
O3S—Na1—O5	161.49 (7)	C15A—C25—H25A	108.2
O2—Na1—O2S	135.03 (6)	C26—C25—H25A	108.2
O3S—Na1—O2S	81.08 (5)	C27—C25—H25A	108.2
O5—Na1—O2S	83.32 (5)	C26—C25—H25B	104.5
O2—Na1—O4ⁱ	136.61 (6)	C27—C25—H25B	104.5
O3S—Na1—O4ⁱ	105.50 (6)	C15B—C25—H25B	104.5
O5—Na1—O4ⁱ	82.41 (5)	C16A—C15A—C24A	118.0 (3)
O2S—Na1—O4ⁱ	83.33 (4)	C16A—C15A—C25	116.8 (3)
O2—Na1—O1Sⁱⁱ	78.92 (5)	C24A—C15A—C25	125.0 (3)
O3S—Na1—O1Sⁱⁱ	109.52 (6)	C15A—C16A—C17A	121.9 (3)
O5—Na1—O1Sⁱⁱ	88.96 (5)	C15A—C16A—H16A	119.1
O2S—Na1—O1Sⁱⁱ	143.32 (5)	C17A—C16A—H16A	119.1
O4ⁱ—Na1—O1Sⁱⁱ	60.08 (4)	C18A—C17A—C22A	118.8 (3)
O5—Na2—O1S	122.60 (6)	C18A—C17A—C16A	121.9 (2)
O5—Na2—O4ⁱ	82.29 (4)	C22A—C17A—C16A	119.2 (3)
O1S—Na2—O4ⁱ	145.68 (5)	C19A—C18A—C17A	120.2 (2)
O5—Na2—O2S	81.75 (4)	C19A—C18A—H18A	119.9
O1S—Na2—O2S	80.06 (5)	C17A—C18A—H18A	119.9
O4ⁱ—Na2—O2S	81.00 (5)	C18A—C19A—C20A	121.3 (2)
O5—Na2—O1ⁱ	85.41 (4)	C18A—C19A—H19A	119.3
O1S—Na2—O1ⁱ	105.56 (5)	C20A—C19A—H19A	119.3
O4ⁱ—Na2—O1ⁱ	99.18 (5)	O6A—C20A—C21A	126.4 (3)
O2S—Na2—O1ⁱ	167.02 (5)	O6A—C20A—C19A	113.4 (2)
O5—Na2—O2ⁱ	135.92 (5)	C21A—C20A—C19A	120.1 (2)
O1S—Na2—O2ⁱ	83.41 (6)	C20A—C21A—C22A	119.5 (3)
O4ⁱ—Na2—O2ⁱ	94.01 (5)	C20A—C21A—H21A	120.3
O2S—Na2—O2ⁱ	141.32 (5)	C22A—C21A—H21A	120.3
O1ⁱ—Na2—O2ⁱ	51.64 (4)	C23A—C22A—C17A	118.4 (3)
O5—Na2—O5ⁱ	130.41 (3)	C23A—C22A—C21A	121.6 (3)
O1S—Na2—O5ⁱ	95.26 (5)	C17A—C22A—C21A	120.0 (3)
O4ⁱ—Na2—O5ⁱ	51.90 (4)	C24A—C23A—C22A	120.8 (2)
O2S—Na2—O5ⁱ	74.12 (4)	C24A—C23A—H23A	119.6
O1ⁱ—Na2—O5ⁱ	116.29 (5)	C22A—C23A—H23A	119.6
O2ⁱ—Na2—O5ⁱ	72.89 (4)	C23A—C24A—C15A	121.7 (3)
C12—O1—Na2ⁱⁱ	92.32 (9)	C23A—C24A—H24A	119.1
C12—O2—Na1	168.53 (13)	C15A—C24A—H24A	119.1
C12—O2—Na2ⁱⁱ	92.62 (10)	O6A—C28A—H28A	109.5
Na1—O2—Na2ⁱⁱ	83.11 (5)	O6A—C28A—H28B	109.5
C6—O3—C14	116.94 (15)	H28A—C28A—H28B	109.5
C27—O4—Na1ⁱⁱ	130.88 (11)	O6A—C28A—H28C	109.5
C27—O4—Na2ⁱⁱ	92.75 (9)	H28A—C28A—H28C	109.5
Na1ⁱⁱ—O4—Na2ⁱⁱ	79.35 (4)	H28B—C28A—H28C	109.5
C27—O5—Na2	132.87 (10)	C20A—O6A—C28A	117.2 (2)
C27—O5—Na1	137.71 (10)	C1S—O1S—Na2	132.12 (12)
Na2—O5—Na1	83.49 (4)	C1S—O1S—Na1ⁱ	102.53 (14)
C27—O5—Na2ⁱⁱ	86.79 (9)	Na2—O1S—Na1ⁱ	74.36 (5)
Na2—O5—Na2ⁱⁱ	130.68 (5)	C1S—O1S—H1S	105.9 (19)
Na1—O5—Na2ⁱⁱ	79.62 (4)	Na2—O1S—H1S	116.5 (19)
C2—C1—C10	118.34 (13)	Na1ⁱ—O1S—H1S	69.3 (19)
C2—C1—C11	122.36 (13)	O1S—C1S—H1S1	109.5
C10—C1—C11	119.30 (13)	O1S—C1S—H1S2	109.5
C1—C2—C3	121.66 (13)	H1S1—C1S—H1S2	109.5
C1—C2—H2	119.2	O1S—C1S—H1S3	109.5
C3—C2—H2	119.2	H1S1—C1S—H1S3	109.5
C8—C3—C2	119.54 (14)	H1S2—C1S—H1S3	109.5
C8—C3—C4	118.47 (14)	C2S—O2S—Na1	113.32 (13)
C2—C3—C4	121.97 (14)	C2S—O2S—Na2	133.15 (13)
C5—C4—C3	120.60 (15)	Na1—O2S—Na2	80.22 (4)
C5—C4—H4	119.7	C2S—O2S—H2S	107 (2)
C3—C4—H4	119.7	Na1—O2S—H2S	108 (2)
C4—C5—C6	120.47 (16)	Na2—O2S—H2S	110 (2)
C4—C5—H5	119.8	O2S—C2S—H2S1	109.5
C6—C5—H5	119.8	O2S—C2S—H2S2	109.5
O3—C6—C7	125.10 (16)	H2S1—C2S—H2S2	109.5
O3—C6—C5	114.18 (15)	O2S—C2S—H2S3	109.5
C7—C6—C5	120.73 (15)	H2S1—C2S—H2S3	109.5
C6—C7—C8	119.44 (15)	H2S2—C2S—H2S3	109.5
C6—C7—H7	120.3	C3S—O3S—Na1	137.38 (12)
C8—C7—H7	120.3	C3S—O3S—H3S	115 (2)
C3—C8—C9	118.21 (13)	Na1—O3S—H3S	108 (2)
C3—C8—C7	120.21 (14)	O3S—C3S—H3S1	109.5
C9—C8—C7	121.56 (14)	O3S—C3S—H3S2	109.5
C10—C9—C8	120.81 (14)	H3S1—C3S—H3S2	109.5
C10—C9—H9	119.6	O3S—C3S—H3S3	109.5
C8—C9—H9	119.6	H3S1—C3S—H3S3	109.5
C9—C10—C1	121.35 (14)	H3S2—C3S—H3S3	109.5
C9—C10—H10	119.3	C28B—O6B—C20B	112.7 (10)
C1—C10—H10	119.3	C16B—C15B—C24B	119.8 (7)
C1—C11—C13	111.54 (13)	C16B—C15B—C25	119.3 (6)
C1—C11—C12	110.58 (12)	C24B—C15B—C25	120.9 (6)
C13—C11—C12	112.24 (13)	C23B—C24B—C15B	120.8 (7)
C1—C11—H11	107.4	C23B—C24B—H24B	119.6
C13—C11—H11	107.4	C15B—C24B—H24B	119.6
C12—C11—H11	107.4	C24B—C23B—C22B	120.2 (7)
O2—C12—O1	123.40 (14)	C24B—C23B—H23B	119.9
O2—C12—C11	118.90 (14)	C22B—C23B—H23B	119.9
O1—C12—C11	117.67 (13)	C23B—C22B—C17B	119.1 (7)
O2—C12—Na2ⁱⁱ	61.83 (9)	C23B—C22B—C21B	122.0 (8)
O1—C12—Na2ⁱⁱ	61.59 (8)	C17B—C22B—C21B	118.9 (8)
C11—C12—Na2ⁱⁱ	179.19 (11)	C20B—C21B—C22B	118.4 (8)
C11—C13—H13A	109.5	C20B—C21B—H21B	120.8
C11—C13—H13B	109.5	C22B—C21B—H21B	120.8
H13A—C13—H13B	109.5	C21B—C20B—C19B	123.1 (7)
C11—C13—H13C	109.5	C21B—C20B—O6B	126.6 (10)
H13A—C13—H13C	109.5	C19B—C20B—O6B	110.4 (9)
H13B—C13—H13C	109.5	C18B—C19B—C20B	119.5 (8)
O3—C14—H14A	109.5	C18B—C19B—H19B	120.3
O3—C14—H14B	109.5	C20B—C19B—H19B	120.3
H14A—C14—H14B	109.5	C19B—C18B—C17B	121.3 (10)
O3—C14—H14C	109.5	C19B—C18B—H18B	119.3
H14A—C14—H14C	109.5	C17B—C18B—H18B	119.3
H14B—C14—H14C	109.5	C15B—C16B—C17B	121.9 (8)
O5—C27—O4	123.49 (14)	C15B—C16B—H16B	119.0
O5—C27—C25	118.22 (14)	C17B—C16B—H16B	119.0
O4—C27—C25	118.26 (14)	C18B—C17B—C16B	123.1 (10)
C25—C26—H26A	109.5	C18B—C17B—C22B	118.8 (9)
C25—C26—H26B	109.5	C16B—C17B—C22B	118.1 (9)
H26A—C26—H26B	109.5	O6B—C28B—H28D	109.5
C25—C26—H26C	109.5	O6B—C28B—H28E	109.5
H26A—C26—H26C	109.5	H28D—C28B—H28E	109.5
H26B—C26—H26C	109.5	O6B—C28B—H28F	109.5
C15A—C25—C26	110.1 (2)	H28D—C28B—H28F	109.5
C15A—C25—C27	113.69 (18)	H28E—C28B—H28F	109.5
C26—C25—C27	108.29 (15)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1S···O4ⁱⁱⁱ	0.84 (2)	1.90 (2)	2.6756 (18)	153 (3)
O2S—H2S···O1ⁱⁱⁱ	0.83 (2)	2.06 (2)	2.8331 (18)	156 (3)
O3S—H3S···O1ⁱⁱⁱ	0.79 (2)	1.94 (2)	2.7226 (19)	172 (3)

Symmetry code: (iii) x, y−1, z.

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