catena-Poly[[[aqua(7-hydroxy-2H-1-benzopyran-2-one)sodium]-di-μ-aqua] 2-oxo-2H-1-benzopyran-7-olate monohydrate]

Zheng, F.; Chen, Y.; Ni, J.; Wang, J.; Shi, G.

doi:10.1107/S160053681002341X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages m834-m835

doi:10.1107/S160053681002341X

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catena-Poly[[[aqua(7-hydroxy-2H-1-benzopyran-2-one)sodium]-di-μ-aqua] 2-oxo-2H-1-benzopyran-7-olate monohydrate]

Fuchun Zheng,^a Yicun Chen,^b ^*‡ Jia Ni,^c Jinzhi Wang ^d and Ganggang Shi ^b

^aDepartment of Pharmacy, First Affiliated Hospital, Shantou University Medical College, Shantou 515041, People's Republic of China, ^bDepartment of Pharmacology, Shantou University Medical College, Shantou 515041, People's Republic of China, ^cAnalysis and Testing Center, Shantou University, Shantou 515041, People's Republic of China, and ^dDepartment of Chemistry, Shantou University Medical College, Shantou 515041, People's Republic of China
^*Correspondence e-mail: ycchen@stu.edu.cn

(Received 10 June 2010; accepted 17 June 2010; online 23 June 2010)

The asymmetric unit of the title compound, {[Na(C₉H₆O₃)(H₂O)₃](C₉H₅O₃)·H₂O}_n, contains two crystallographically independent Na atoms, two 7-hydroxycoumarin ligands, six coordinated water molecules, two 7-hydroxycoumarin anions and two uncoordinated water molecules. Both Na atoms exhibit a distorted octahedral coordination geometry and are coordinated by five water O atoms and the terminal O atom from a 7-hydroxycoumarin ligand. Four of the water molecules are bridging, whereas the fifth is terminal. Na—O bond distances are in the range 2.288 (2)–2.539 (2) Å. In the chains, extending parallel to [100], adjacent Na atoms are separated by 3.60613 (7) Å. The uncoordinated water molecules and 7-hydroxycoumarin phenolate anions are located between the chains and are hydrogen bonded to the chains.

Related literature

For applications of the active drug umbelliferone (7-hydroxycoumarin, 7-HOC), see: Toyama et al. (2009 ); Egan et al. (1990 ). For applications of metal complexes of coumarin, see: Nath et al. (2005 ).

Experimental

Crystal data

[Na(C₉H₆O₃)(H₂O)₃](C₉H₅O₃)·H₂O
M_r = 836.64
Monoclinic, P 2/c
a = 11.7803 (5) Å
b = 7.6462 (3) Å
c = 42.3249 (17) Å
β = 102.184 (1)°
V = 3726.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 173 K
0.46 × 0.44 × 0.39 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.938, T_max = 0.947
16682 measured reflections
7251 independent reflections
5790 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.153
S = 1.13
7251 reflections
573 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8W—H8B⋯O47ⁱ	0.91 (4)	1.78 (4)	2.658 (3)	162 (4)
O8W—H8A⋯O1Wⁱⁱ	0.83 (4)	2.02 (4)	2.809 (3)	159 (4)
O7W—H7A⋯O12ⁱⁱⁱ	0.77 (4)	2.43 (4)	3.068 (3)	141 (4)
O7W—H7B⋯O35	0.94 (4)	1.73 (4)	2.668 (3)	180 (5)
O6W—H6B⋯O12ⁱ	0.84 (4)	2.09 (4)	2.913 (3)	165 (3)
O6W—H6A⋯O35ⁱ	0.84 (4)	2.06 (4)	2.843 (3)	156 (3)
O5W—H5B⋯O47ⁱ	0.86 (4)	1.96 (4)	2.799 (3)	167 (4)
O5W—H5A⋯O7Wⁱ	0.76 (4)	2.07 (4)	2.819 (3)	171 (4)
O4W—H4B⋯O47^iv	0.86 (4)	1.92 (4)	2.776 (3)	171 (3)
O4W—H4A⋯O7W^v	0.89 (4)	1.98 (4)	2.854 (3)	164 (3)
O3W—H3B⋯O8W	0.83 (4)	1.98 (4)	2.796 (3)	170 (3)
O3W—H3A⋯O35	0.82 (4)	2.01 (4)	2.804 (3)	164 (3)
O2W—H2B⋯O24	0.83 (4)	2.20 (4)	2.932 (3)	148 (3)
O2W—H2A⋯O47^iv	0.89 (4)	2.01 (4)	2.870 (3)	164 (3)
O1W—H1B⋯O8W^v	0.84 (4)	2.08 (4)	2.897 (4)	164 (3)
O1W—H1A⋯O35^v	0.91 (4)	1.83 (4)	2.739 (3)	174 (3)
O23—H23⋯O36^vi	0.84	1.83	2.664 (3)	175
O11—H11⋯O48^vii	0.84	1.81	2.641 (3)	173
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-1, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x+1, y+1, -z+{\script{1\over 2}}]$ ; (v) x, y+1, z; (vi) $[x, -y+1, z+{\script{1\over 2}}]$ ; (vii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002341X/rk2209sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002341X/rk2209Isup2.hkl

checkCIF report

Comment top

It has been suggested that coumarin (1,2-benzopyrone) may be a pro-drug and its major biotransformed product 7-hydroxycoumarin, also known as umbelliferone, is an active drug (Egan et al., 1990). The 7-hydroxycoumarin is also a widely distributed natural product which shows anti-imflammatory activity (Toyama et al., 2009), and the complexes of coumarin with metal have increased bioactivities such as anti-imflammatory activity (Nath et al., 2005). We synthesized the complexe of 7-hydroxycoumarin with sodium for further bioactivities study. This paper is devoted to the crystal structure of the sodium salt of 7-hydroxycoumarin.

The molecular structure of the title compound is shown in Fig. 1. The main moiety of crystal structure is build up of cation chains - (C₁₈H₂₄Na₂O₁₂)²⁺_n. The polymeric chain contains two independent crystallographic Na centers. Both Na atoms is six-coordinated by five O atoms of water molecules and one O atom of a ligand. Each 7-hydroxycoumarin ligand links Na centers via its O atom of carbonyl group in a chelating manner. Oxygen atoms of two water are bridging atom between two sodium atoms. Na—O bond distances are in the range of 2.288 (2)–2.539 (2)Å. In the chain, two adjacent Na1···Na2 distance of 3.60613 (7)Å. In addition, two 7-hydroxycoumarin anions and two water molecules are hydrogen bonded to the chains.

Related literature top

For applications of the active drug umbelliferone (7-hydroxycoumarin, 7-HOC), see: Toyama et al. (2009); Egan et al. (1990). For applications of metal complexes of coumarin, see: Nath et al. (2005).

Experimental top

A stoichiometric amount of NaOH (0.25 mmol) and a quantitative amount of 7-hydroxycoumarin (0.5 mmol) were mixed and then dissolved in ethanol (20 ml). The pH value of the solution was about to 6.5. The solution mixture was stirred continuously for 2 h at room temperature and then filtered. Single crystals were obtained by evaporation after one week.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A portion of the infinite chain of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. The H atoms are presented as a small spheres of arbitrary radius.

catena-Poly[[[aqua(7-hydroxy-2H-1-benzopyran-2-one)sodium]- di-µ-aqua] 2-oxo-2H-1-benzopyran-7-olate monohydrate] top

Crystal data top

[Na(C₉H₆O₃)(H₂O)₃](C₉H₅O₃)·H₂O	F(000) = 1744
M_r = 418.32	D_x = 1.491 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 8701 reflections
a = 11.7803 (5) Å	θ = 2.4–27.0°
b = 7.6462 (3) Å	µ = 0.14 mm⁻¹
c = 42.3249 (17) Å	T = 173 K
β = 102.184 (1)°	Block, yellow
V = 3726.5 (3) Å³	0.46 × 0.44 × 0.39 mm
Z = 8

Data collection top

Bruker SMART 1000 CCD diffractometer	7251 independent reflections
Radiation source: fine-focus sealed tube	5790 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ– and ω–scans	θ_max = 26.0°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→10
T_min = 0.938, T_max = 0.947	k = −9→4
16682 measured reflections	l = −43→52

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0397P)² + 6.7016P] where P = (F_o² + 2F_c²)/3
7251 reflections	(Δ/σ)_max < 0.001
573 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Na(C₉H₆O₃)(H₂O)₃](C₉H₅O₃)·H₂O	V = 3726.5 (3) Å³
M_r = 418.32	Z = 8
Monoclinic, P2/c	Mo Kα radiation
a = 11.7803 (5) Å	µ = 0.14 mm⁻¹
b = 7.6462 (3) Å	T = 173 K
c = 42.3249 (17) Å	0.46 × 0.44 × 0.39 mm
β = 102.184 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	7251 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	5790 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.947	R_int = 0.027
16682 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.32 e Å⁻³
7251 reflections	Δρ_min = −0.31 e Å⁻³
573 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	U_iso*/U_eq
O1	0.23526 (16)	0.8756 (3)	0.13635 (4)	0.0257 (4)
C2	0.1713 (2)	0.9338 (4)	0.15762 (6)	0.0257 (6)
C3	0.0611 (2)	1.0154 (4)	0.14468 (7)	0.0281 (6)
H3	0.0156	1.0592	0.1590	0.034*
C4	0.0218 (2)	1.0302 (4)	0.11256 (7)	0.0261 (6)
H4	−0.0505	1.0862	0.1045	0.031*
C5	0.0514 (2)	0.9665 (4)	0.05654 (7)	0.0291 (6)
H5	−0.0211	1.0182	0.0470	0.035*
C6	0.1193 (3)	0.8967 (4)	0.03704 (7)	0.0301 (6)
H6	0.0940	0.9004	0.0142	0.036*
C7	0.2261 (2)	0.8199 (4)	0.05101 (7)	0.0279 (6)
C8	0.2640 (2)	0.8138 (4)	0.08425 (6)	0.0245 (6)
H8	0.3364	0.7616	0.0937	0.029*
C9	0.1945 (2)	0.8848 (4)	0.10340 (6)	0.0220 (6)
C10	0.0873 (2)	0.9629 (4)	0.09044 (6)	0.0235 (6)
O11	0.29631 (18)	0.7479 (3)	0.03313 (5)	0.0401 (6)
H11	0.2643	0.7539	0.0134	0.060*
O12	0.21478 (18)	0.9155 (3)	0.18627 (5)	0.0335 (5)
O13	0.26587 (16)	0.7216 (3)	0.36781 (4)	0.0262 (4)
C14	0.3302 (2)	0.6748 (4)	0.34559 (7)	0.0256 (6)
C15	0.4381 (2)	0.5838 (4)	0.35722 (7)	0.0288 (6)
H15	0.4838	0.5487	0.3423	0.035*
C16	0.4752 (2)	0.5479 (4)	0.38881 (7)	0.0270 (6)
H16	0.5456	0.4854	0.3959	0.032*
C17	0.4438 (2)	0.5750 (4)	0.44534 (7)	0.0276 (6)
H17	0.5147	0.5161	0.4538	0.033*
C18	0.3760 (2)	0.6316 (4)	0.46607 (7)	0.0287 (6)
H18	0.4001	0.6119	0.4887	0.034*
C19	0.2712 (2)	0.7186 (4)	0.45381 (7)	0.0278 (6)
C20	0.2354 (2)	0.7486 (4)	0.42082 (6)	0.0257 (6)
H20	0.1646	0.8080	0.4124	0.031*
C21	0.3050 (2)	0.6901 (4)	0.40041 (6)	0.0227 (6)
C22	0.4097 (2)	0.6028 (3)	0.41194 (7)	0.0236 (6)
O23	0.20131 (19)	0.7771 (3)	0.47295 (5)	0.0395 (6)
H23	0.2314	0.7544	0.4923	0.059*
O24	0.28986 (18)	0.7130 (3)	0.31755 (5)	0.0330 (5)
O25	0.26302 (16)	0.3348 (3)	0.08489 (4)	0.0278 (4)
C26	0.2189 (3)	0.3358 (4)	0.05220 (7)	0.0297 (6)
C27	0.1023 (3)	0.3955 (4)	0.04096 (7)	0.0344 (7)
H27	0.0697	0.3967	0.0184	0.041*
C28	0.0378 (3)	0.4502 (4)	0.06194 (7)	0.0331 (7)
H28	−0.0392	0.4905	0.0540	0.040*
C29	0.0240 (3)	0.5025 (4)	0.11978 (8)	0.0324 (7)
H29	−0.0537	0.5432	0.1134	0.039*
C30	0.0755 (3)	0.4976 (4)	0.15192 (7)	0.0317 (7)
H30	0.0332	0.5363	0.1674	0.038*
C31	0.1910 (2)	0.4359 (4)	0.16264 (7)	0.0265 (6)
C32	0.2516 (2)	0.3821 (4)	0.13896 (7)	0.0255 (6)
H32	0.3292	0.3408	0.1452	0.031*
C33	0.1980 (2)	0.3895 (4)	0.10683 (6)	0.0234 (6)
C34	0.0839 (2)	0.4482 (4)	0.09587 (7)	0.0282 (6)
O35	0.23967 (17)	0.4289 (3)	0.19366 (5)	0.0304 (5)
O36	0.28529 (18)	0.2832 (3)	0.03552 (5)	0.0381 (5)
O37	0.76263 (16)	0.2269 (3)	0.07958 (4)	0.0288 (5)
C38	0.7208 (3)	0.2060 (4)	0.04703 (7)	0.0304 (7)
C39	0.6054 (3)	0.1389 (4)	0.03655 (7)	0.0339 (7)
H39	0.5743	0.1236	0.0141	0.041*
C40	0.5402 (3)	0.0973 (4)	0.05811 (8)	0.0331 (7)
H40	0.4638	0.0533	0.0507	0.040*
C41	0.5241 (3)	0.0783 (4)	0.11626 (8)	0.0334 (7)
H41	0.4466	0.0363	0.1104	0.040*
C42	0.5743 (3)	0.0983 (4)	0.14834 (8)	0.0317 (7)
H42	0.5313	0.0686	0.1642	0.038*
C43	0.6895 (2)	0.1626 (4)	0.15829 (7)	0.0260 (6)
C44	0.7499 (2)	0.2065 (4)	0.13408 (7)	0.0260 (6)
H44	0.8266	0.2521	0.1398	0.031*
C45	0.6974 (2)	0.1832 (4)	0.10207 (7)	0.0247 (6)
C46	0.5847 (2)	0.1184 (4)	0.09187 (7)	0.0277 (6)
O47	0.73790 (17)	0.1803 (3)	0.18917 (5)	0.0320 (5)
O48	0.78815 (18)	0.2480 (3)	0.02986 (5)	0.0390 (5)
O1W	0.10600 (19)	1.2312 (3)	0.22568 (6)	0.0340 (5)
H1A	0.153 (3)	1.290 (5)	0.2146 (8)	0.041*
H1B	0.119 (3)	1.275 (5)	0.2443 (9)	0.041*
O2W	0.08624 (18)	0.9228 (3)	0.28844 (5)	0.0296 (5)
H2A	0.130 (3)	1.013 (5)	0.2967 (8)	0.036*
H2B	0.122 (3)	0.835 (5)	0.2963 (8)	0.036*
O3W	0.17663 (18)	0.6416 (3)	0.24113 (5)	0.0288 (5)
H3A	0.182 (3)	0.584 (5)	0.2253 (8)	0.035*
H3B	0.148 (3)	0.574 (5)	0.2525 (8)	0.035*
O4W	0.32795 (19)	0.9807 (3)	0.26292 (5)	0.0306 (5)
H4A	0.358 (3)	1.057 (5)	0.2509 (8)	0.037*
H4B	0.315 (3)	1.043 (5)	0.2787 (8)	0.037*
O5W	0.3969 (2)	0.3917 (3)	0.27914 (6)	0.0382 (6)
H5A	0.454 (3)	0.344 (5)	0.2824 (9)	0.046*
H5B	0.358 (3)	0.338 (5)	0.2912 (9)	0.046*
O6W	0.58882 (18)	0.6911 (3)	0.28677 (5)	0.0293 (5)
H6A	0.624 (3)	0.602 (5)	0.2951 (8)	0.035*
H6B	0.636 (3)	0.769 (5)	0.2949 (8)	0.035*
O7W	0.4008 (2)	0.1863 (4)	0.21454 (6)	0.0451 (6)
H7A	0.382 (4)	0.104 (6)	0.2044 (10)	0.054*
H7B	0.344 (3)	0.272 (5)	0.2073 (9)	0.054*
O8W	0.1042 (2)	0.4173 (4)	0.28519 (6)	0.0444 (6)
H8A	0.043 (4)	0.370 (5)	0.2869 (9)	0.053*
H8B	0.159 (3)	0.349 (5)	0.2979 (9)	0.053*
Na1	0.12359 (9)	0.92812 (14)	0.23211 (3)	0.0257 (3)
Na2	0.37973 (9)	0.69032 (14)	0.27077 (3)	0.0251 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0223 (10)	0.0322 (11)	0.0216 (9)	0.0050 (8)	0.0025 (8)	0.0016 (8)
C2	0.0273 (14)	0.0271 (14)	0.0229 (14)	−0.0006 (12)	0.0062 (11)	−0.0016 (11)
C3	0.0247 (14)	0.0322 (15)	0.0285 (15)	0.0032 (12)	0.0084 (12)	−0.0009 (12)
C4	0.0209 (14)	0.0254 (14)	0.0313 (15)	0.0031 (11)	0.0037 (11)	−0.0020 (12)
C5	0.0232 (14)	0.0316 (16)	0.0294 (15)	0.0035 (12)	−0.0014 (11)	0.0021 (12)
C6	0.0295 (15)	0.0360 (16)	0.0222 (14)	0.0015 (13)	−0.0002 (12)	0.0017 (12)
C7	0.0266 (15)	0.0315 (15)	0.0261 (14)	0.0002 (12)	0.0069 (11)	−0.0013 (12)
C8	0.0184 (13)	0.0273 (14)	0.0270 (14)	0.0026 (11)	0.0026 (11)	0.0012 (12)
C9	0.0214 (13)	0.0227 (13)	0.0204 (13)	−0.0019 (11)	0.0014 (10)	0.0010 (11)
C10	0.0196 (13)	0.0243 (14)	0.0257 (14)	0.0004 (11)	0.0032 (11)	0.0013 (11)
O11	0.0342 (12)	0.0614 (16)	0.0245 (10)	0.0128 (11)	0.0057 (9)	−0.0046 (11)
O12	0.0357 (12)	0.0416 (13)	0.0224 (10)	0.0074 (10)	0.0042 (9)	0.0032 (9)
O13	0.0241 (10)	0.0314 (11)	0.0225 (10)	0.0052 (8)	0.0034 (8)	0.0023 (8)
C14	0.0275 (14)	0.0242 (14)	0.0258 (14)	−0.0016 (12)	0.0071 (11)	0.0004 (11)
C15	0.0259 (15)	0.0279 (15)	0.0339 (15)	0.0017 (12)	0.0089 (12)	−0.0019 (12)
C16	0.0196 (13)	0.0249 (14)	0.0351 (15)	−0.0011 (11)	0.0025 (11)	0.0021 (12)
C17	0.0222 (14)	0.0282 (15)	0.0297 (15)	−0.0002 (12)	−0.0011 (11)	0.0029 (12)
C18	0.0290 (15)	0.0325 (16)	0.0222 (14)	−0.0032 (13)	−0.0002 (11)	0.0055 (12)
C19	0.0269 (14)	0.0307 (15)	0.0258 (14)	−0.0034 (12)	0.0054 (11)	−0.0004 (12)
C20	0.0190 (13)	0.0304 (15)	0.0263 (14)	0.0009 (12)	0.0017 (11)	0.0009 (12)
C21	0.0209 (13)	0.0238 (13)	0.0216 (13)	−0.0037 (11)	0.0008 (10)	0.0029 (11)
C22	0.0208 (13)	0.0188 (13)	0.0299 (14)	−0.0028 (11)	0.0026 (11)	0.0020 (11)
O23	0.0358 (12)	0.0591 (15)	0.0242 (10)	0.0091 (11)	0.0078 (9)	0.0017 (11)
O24	0.0351 (11)	0.0403 (12)	0.0234 (10)	0.0050 (10)	0.0059 (9)	0.0011 (9)
O25	0.0218 (10)	0.0370 (11)	0.0248 (10)	0.0010 (9)	0.0051 (8)	0.0004 (9)
C26	0.0284 (15)	0.0350 (16)	0.0248 (14)	−0.0039 (13)	0.0036 (12)	0.0028 (12)
C27	0.0323 (16)	0.0403 (18)	0.0269 (15)	0.0021 (14)	−0.0027 (12)	0.0065 (13)
C28	0.0243 (15)	0.0323 (16)	0.0392 (17)	0.0038 (13)	−0.0009 (13)	0.0041 (14)
C29	0.0252 (15)	0.0283 (15)	0.0449 (18)	0.0045 (12)	0.0105 (13)	0.0026 (13)
C30	0.0308 (16)	0.0290 (15)	0.0387 (17)	0.0020 (13)	0.0149 (13)	−0.0026 (13)
C31	0.0289 (15)	0.0225 (14)	0.0291 (15)	−0.0051 (12)	0.0086 (12)	−0.0017 (12)
C32	0.0186 (13)	0.0284 (15)	0.0296 (14)	0.0000 (11)	0.0051 (11)	0.0009 (12)
C33	0.0224 (14)	0.0218 (13)	0.0270 (14)	−0.0011 (11)	0.0073 (11)	0.0006 (11)
C34	0.0233 (14)	0.0258 (14)	0.0353 (16)	0.0001 (12)	0.0055 (12)	0.0033 (12)
O35	0.0331 (11)	0.0320 (11)	0.0273 (10)	−0.0018 (9)	0.0093 (9)	−0.0019 (9)
O36	0.0334 (12)	0.0544 (15)	0.0267 (11)	0.0030 (11)	0.0067 (9)	0.0000 (10)
O37	0.0208 (10)	0.0409 (12)	0.0239 (10)	0.0017 (9)	0.0027 (8)	−0.0034 (9)
C38	0.0297 (15)	0.0353 (16)	0.0241 (14)	0.0079 (13)	0.0010 (12)	−0.0061 (12)
C39	0.0311 (16)	0.0363 (17)	0.0293 (15)	0.0037 (14)	−0.0047 (12)	−0.0078 (13)
C40	0.0237 (15)	0.0307 (16)	0.0415 (17)	0.0017 (13)	−0.0009 (13)	−0.0039 (13)
C41	0.0210 (14)	0.0297 (16)	0.0485 (19)	−0.0015 (12)	0.0048 (13)	−0.0023 (14)
C42	0.0290 (15)	0.0261 (15)	0.0420 (17)	0.0008 (12)	0.0120 (13)	0.0063 (13)
C43	0.0262 (14)	0.0207 (14)	0.0311 (15)	0.0042 (11)	0.0065 (12)	0.0002 (11)
C44	0.0193 (13)	0.0292 (15)	0.0289 (14)	0.0004 (11)	0.0036 (11)	−0.0005 (12)
C45	0.0207 (13)	0.0259 (14)	0.0277 (14)	0.0049 (11)	0.0056 (11)	−0.0023 (12)
C46	0.0218 (14)	0.0237 (14)	0.0355 (16)	0.0022 (11)	0.0015 (12)	−0.0040 (12)
O47	0.0313 (11)	0.0371 (12)	0.0286 (11)	0.0023 (9)	0.0086 (9)	0.0042 (9)
O48	0.0322 (12)	0.0584 (15)	0.0269 (11)	0.0011 (11)	0.0071 (9)	−0.0055 (10)
O1W	0.0356 (12)	0.0305 (12)	0.0401 (12)	−0.0022 (10)	0.0175 (10)	−0.0003 (10)
O2W	0.0251 (11)	0.0322 (12)	0.0304 (11)	0.0033 (9)	0.0030 (8)	0.0006 (9)
O3W	0.0342 (12)	0.0238 (11)	0.0300 (11)	−0.0007 (9)	0.0101 (9)	0.0003 (9)
O4W	0.0380 (12)	0.0269 (11)	0.0298 (11)	−0.0024 (9)	0.0139 (9)	0.0000 (9)
O5W	0.0362 (13)	0.0244 (11)	0.0600 (15)	0.0047 (10)	0.0233 (12)	0.0088 (10)
O6W	0.0242 (11)	0.0293 (11)	0.0325 (11)	−0.0018 (9)	0.0017 (9)	−0.0006 (9)
O7W	0.0342 (13)	0.0483 (15)	0.0520 (16)	−0.0033 (12)	0.0073 (11)	0.0151 (12)
O8W	0.0278 (12)	0.0590 (16)	0.0465 (14)	−0.0053 (12)	0.0082 (10)	0.0183 (12)
Na1	0.0269 (6)	0.0251 (6)	0.0259 (6)	0.0026 (5)	0.0074 (4)	0.0019 (4)
Na2	0.0245 (6)	0.0259 (6)	0.0253 (5)	0.0003 (5)	0.0059 (4)	0.0010 (4)

Geometric parameters (Å, º) top

O1—C2	1.365 (3)	C30—H30	0.9500
O1—C9	1.378 (3)	C31—O35	1.318 (3)
C2—O12	1.221 (3)	C31—C32	1.410 (4)
C2—C3	1.440 (4)	C32—C33	1.375 (4)
C3—C4	1.345 (4)	C32—H32	0.9500
C3—H3	0.9500	C33—C34	1.400 (4)
C4—C10	1.429 (4)	O37—C38	1.371 (3)
C4—H4	0.9500	O37—C45	1.385 (3)
C5—C6	1.373 (4)	C38—O48	1.226 (4)
C5—C10	1.408 (4)	C38—C39	1.433 (4)
C5—H5	0.9500	C39—C40	1.348 (4)
C6—C7	1.401 (4)	C39—H39	0.9500
C6—H6	0.9500	C40—C46	1.423 (4)
C7—O11	1.351 (3)	C40—H40	0.9500
C7—C8	1.384 (4)	C41—C42	1.370 (4)
C8—C9	1.379 (4)	C41—C46	1.407 (4)
C8—H8	0.9500	C41—H41	0.9500
C9—C10	1.400 (4)	C42—C43	1.421 (4)
O11—H11	0.8400	C42—H42	0.9500
O12—Na1	2.410 (2)	C43—O47	1.318 (3)
O13—C14	1.374 (3)	C43—C44	1.407 (4)
O13—C21	1.380 (3)	C44—C45	1.377 (4)
C14—O24	1.217 (3)	C44—H44	0.9500
C14—C15	1.442 (4)	C45—C46	1.397 (4)
C15—C16	1.344 (4)	O1W—Na1	2.338 (2)
C15—H15	0.9500	O1W—H1A	0.91 (4)
C16—C22	1.431 (4)	O1W—H1B	0.84 (4)
C16—H16	0.9500	O2W—Na1ⁱ	2.442 (2)
C17—C18	1.375 (4)	O2W—Na1	2.514 (2)
C17—C22	1.402 (4)	O2W—H2A	0.89 (4)
C17—H17	0.9500	O2W—H2B	0.83 (4)
C18—C19	1.402 (4)	O3W—Na1	2.288 (2)
C18—H18	0.9500	O3W—Na2	2.484 (2)
C19—O23	1.347 (3)	O3W—H3A	0.82 (4)
C19—C20	1.390 (4)	O3W—H3B	0.83 (4)
C20—C21	1.385 (4)	O4W—Na2	2.308 (2)
C20—H20	0.9500	O4W—Na1	2.516 (2)
C21—C22	1.397 (4)	O4W—H4A	0.89 (4)
O23—H23	0.8400	O4W—H4B	0.86 (4)
O24—Na2	2.440 (2)	O5W—Na2	2.313 (2)
O25—C26	1.372 (3)	O5W—H5A	0.76 (4)
O25—C33	1.387 (3)	O5W—H5B	0.86 (4)
C26—O36	1.226 (4)	O6W—Na2	2.413 (2)
C26—C27	1.431 (4)	O6W—Na2ⁱⁱ	2.539 (2)
C27—C28	1.351 (4)	O6W—H6A	0.84 (4)
C27—H27	0.9500	O6W—H6B	0.84 (4)
C28—C34	1.424 (4)	O7W—H7A	0.77 (4)
C28—H28	0.9500	O7W—H7B	0.94 (4)
C29—C30	1.368 (4)	O8W—H8A	0.83 (4)
C29—C34	1.413 (4)	O8W—H8B	0.91 (4)
C29—H29	0.9500	Na1—O2Wⁱ	2.442 (2)
C30—C31	1.421 (4)	Na2—O6Wⁱⁱ	2.539 (2)

C2—O1—C9	121.9 (2)	C41—C42—H42	119.4
O12—C2—O1	116.3 (2)	C43—C42—H42	119.4
O12—C2—C3	125.7 (3)	O47—C43—C44	121.2 (3)
O1—C2—C3	118.0 (2)	O47—C43—C42	121.0 (3)
C4—C3—C2	120.7 (3)	C44—C43—C42	117.8 (3)
C4—C3—H3	119.6	C45—C44—C43	119.6 (3)
C2—C3—H3	119.6	C45—C44—H44	120.2
C3—C4—C10	120.9 (3)	C43—C44—H44	120.2
C3—C4—H4	119.5	C44—C45—O37	116.4 (2)
C10—C4—H4	119.5	C44—C45—C46	123.4 (3)
C6—C5—C10	121.1 (3)	O37—C45—C46	120.2 (2)
C6—C5—H5	119.4	C45—C46—C41	116.5 (3)
C10—C5—H5	119.4	C45—C46—C40	118.4 (3)
C5—C6—C7	119.6 (3)	C41—C46—C40	125.1 (3)
C5—C6—H6	120.2	Na1—O1W—H1A	120 (2)
C7—C6—H6	120.2	Na1—O1W—H1B	107 (3)
O11—C7—C8	116.8 (3)	H1A—O1W—H1B	106 (3)
O11—C7—C6	122.4 (3)	Na1ⁱ—O2W—Na1	91.63 (8)
C8—C7—C6	120.7 (3)	Na1ⁱ—O2W—H2A	126 (2)
C9—C8—C7	118.7 (3)	Na1—O2W—H2A	99 (2)
C9—C8—H8	120.7	Na1ⁱ—O2W—H2B	124 (2)
C7—C8—H8	120.7	Na1—O2W—H2B	102 (2)
O1—C9—C8	116.9 (2)	H2A—O2W—H2B	105 (3)
O1—C9—C10	120.7 (2)	Na1—O3W—Na2	98.08 (9)
C8—C9—C10	122.4 (2)	Na1—O3W—H3A	116 (2)
C9—C10—C5	117.4 (2)	Na2—O3W—H3A	105 (2)
C9—C10—C4	117.7 (2)	Na1—O3W—H3B	124 (2)
C5—C10—C4	125.0 (3)	Na2—O3W—H3B	106 (2)
C7—O11—H11	109.5	H3A—O3W—H3B	105 (3)
C2—O12—Na1	129.07 (19)	Na2—O4W—Na1	96.65 (8)
C14—O13—C21	121.5 (2)	Na2—O4W—H4A	126 (2)
O24—C14—O13	116.5 (2)	Na1—O4W—H4A	105 (2)
O24—C14—C15	125.7 (3)	Na2—O4W—H4B	120 (2)
O13—C14—C15	117.8 (2)	Na1—O4W—H4B	101 (2)
C16—C15—C14	121.1 (3)	H4A—O4W—H4B	103 (3)
C16—C15—H15	119.5	Na2—O5W—H5A	124 (3)
C14—C15—H15	119.5	Na2—O5W—H5B	122 (3)
C15—C16—C22	120.8 (3)	H5A—O5W—H5B	103 (4)
C15—C16—H16	119.6	Na2—O6W—Na2ⁱⁱ	94.47 (8)
C22—C16—H16	119.6	Na2—O6W—H6A	120 (2)
C18—C17—C22	121.0 (3)	Na2ⁱⁱ—O6W—H6A	104 (2)
C18—C17—H17	119.5	Na2—O6W—H6B	132 (2)
C22—C17—H17	119.5	Na2ⁱⁱ—O6W—H6B	100 (2)
C17—C18—C19	119.9 (3)	H6A—O6W—H6B	101 (3)
C17—C18—H18	120.1	H7A—O7W—H7B	107 (4)
C19—C18—H18	120.1	H8A—O8W—H8B	102 (4)
O23—C19—C20	117.0 (3)	O3W—Na1—O1W	169.46 (10)
O23—C19—C18	122.5 (3)	O3W—Na1—O12	86.77 (8)
C20—C19—C18	120.5 (3)	O1W—Na1—O12	89.40 (8)
C21—C20—C19	118.7 (3)	O3W—Na1—O2Wⁱ	105.29 (9)
C21—C20—H20	120.7	O1W—Na1—O2Wⁱ	85.23 (9)
C19—C20—H20	120.7	O12—Na1—O2Wⁱ	107.59 (8)
O13—C21—C20	116.8 (2)	O3W—Na1—O2W	85.56 (8)
O13—C21—C22	121.1 (2)	O1W—Na1—O2W	95.60 (9)
C20—C21—C22	122.1 (2)	O12—Na1—O2W	163.68 (8)
C21—C22—C17	117.9 (3)	O2Wⁱ—Na1—O2W	88.34 (8)
C21—C22—C16	117.7 (2)	O3W—Na1—O4W	82.46 (8)
C17—C22—C16	124.4 (3)	O1W—Na1—O4W	87.34 (8)
C19—O23—H23	109.5	O12—Na1—O4W	83.30 (8)
C14—O24—Na2	128.84 (19)	O2Wⁱ—Na1—O4W	166.71 (9)
C26—O25—C33	121.9 (2)	O2W—Na1—O4W	81.43 (8)
O36—C26—O25	115.3 (3)	O3W—Na1—Na1ⁱ	98.53 (6)
O36—C26—C27	126.7 (3)	O1W—Na1—Na1ⁱ	89.38 (6)
O25—C26—C27	118.0 (3)	O12—Na1—Na1ⁱ	152.55 (8)
C28—C27—C26	120.9 (3)	O2Wⁱ—Na1—Na1ⁱ	45.00 (5)
C28—C27—H27	119.5	O2W—Na1—Na1ⁱ	43.37 (5)
C26—C27—H27	119.5	O4W—Na1—Na1ⁱ	124.02 (7)
C27—C28—C34	120.8 (3)	O3W—Na1—Na2	43.00 (6)
C27—C28—H28	119.6	O1W—Na1—Na2	126.72 (7)
C34—C28—H28	119.6	O12—Na1—Na2	82.68 (6)
C30—C29—C34	121.3 (3)	O2Wⁱ—Na1—Na2	147.20 (7)
C30—C29—H29	119.3	O2W—Na1—Na2	81.88 (6)
C34—C29—H29	119.3	O4W—Na1—Na2	39.47 (5)
C29—C30—C31	121.4 (3)	Na1ⁱ—Na1—Na2	119.28 (4)
C29—C30—H30	119.3	O4W—Na2—O5W	169.64 (10)
C31—C30—H30	119.3	O4W—Na2—O6W	105.13 (9)
O35—C31—C32	121.1 (3)	O5W—Na2—O6W	84.73 (9)
O35—C31—C30	121.2 (3)	O4W—Na2—O24	84.36 (8)
C32—C31—C30	117.7 (3)	O5W—Na2—O24	89.13 (9)
C33—C32—C31	119.7 (3)	O6W—Na2—O24	111.35 (8)
C33—C32—H32	120.2	O4W—Na2—O3W	82.79 (8)
C31—C32—H32	120.2	O5W—Na2—O3W	88.46 (9)
C32—C33—O25	116.5 (2)	O6W—Na2—O3W	163.64 (9)
C32—C33—C34	123.3 (3)	O24—Na2—O3W	83.33 (8)
O25—C33—C34	120.1 (2)	O4W—Na2—O6Wⁱⁱ	86.98 (8)
C33—C34—C29	116.6 (3)	O5W—Na2—O6Wⁱⁱ	97.09 (9)
C33—C34—C28	118.2 (3)	O6W—Na2—O6Wⁱⁱ	85.53 (8)
C29—C34—C28	125.2 (3)	O24—Na2—O6Wⁱⁱ	162.54 (8)
C38—O37—C45	121.9 (2)	O3W—Na2—O6Wⁱⁱ	80.56 (7)
O48—C38—O37	115.1 (3)	O4W—Na2—Na1	43.88 (6)
O48—C38—C39	126.9 (3)	O5W—Na2—Na1	127.24 (8)
O37—C38—C39	117.9 (3)	O6W—Na2—Na1	146.40 (7)
C40—C39—C38	120.9 (3)	O24—Na2—Na1	82.39 (6)
C40—C39—H39	119.6	O3W—Na2—Na1	38.92 (5)
C38—C39—H39	119.6	O6Wⁱⁱ—Na2—Na1	80.86 (6)
C39—C40—C46	120.7 (3)	O4W—Na2—Na2ⁱⁱ	98.02 (6)
C39—C40—H40	119.6	O5W—Na2—Na2ⁱⁱ	91.26 (6)
C46—C40—H40	119.6	O6W—Na2—Na2ⁱⁱ	44.12 (5)
C42—C41—C46	121.5 (3)	O24—Na2—Na2ⁱⁱ	155.23 (7)
C42—C41—H41	119.2	O3W—Na2—Na2ⁱⁱ	121.44 (7)
C46—C41—H41	119.2	O6Wⁱⁱ—Na2—Na2ⁱⁱ	41.41 (5)
C41—C42—C43	121.1 (3)	Na1—Na2—Na2ⁱⁱ	116.32 (4)

C9—O1—C2—O12	178.3 (2)	Na2—O3W—Na1—O2W	−82.85 (8)
C9—O1—C2—C3	−3.5 (4)	Na2—O3W—Na1—O4W	−0.92 (8)
O12—C2—C3—C4	179.3 (3)	Na2—O3W—Na1—Na1ⁱ	−124.35 (7)
O1—C2—C3—C4	1.3 (4)	C2—O12—Na1—O3W	117.1 (3)
C2—C3—C4—C10	1.1 (4)	C2—O12—Na1—O1W	−72.7 (3)
C10—C5—C6—C7	0.2 (5)	C2—O12—Na1—O2Wⁱ	12.1 (3)
C5—C6—C7—O11	179.5 (3)	C2—O12—Na1—O2W	179.2 (3)
C5—C6—C7—C8	0.0 (5)	C2—O12—Na1—O4W	−160.1 (3)
O11—C7—C8—C9	−179.6 (3)	C2—O12—Na1—Na1ⁱ	14.8 (3)
C6—C7—C8—C9	0.0 (4)	C2—O12—Na1—Na2	160.1 (3)
C2—O1—C9—C8	−176.7 (2)	Na1ⁱ—O2W—Na1—O3W	−107.39 (9)
C2—O1—C9—C10	3.2 (4)	Na1ⁱ—O2W—Na1—O1W	83.13 (9)
C7—C8—C9—O1	179.9 (2)	Na1ⁱ—O2W—Na1—O12	−169.6 (3)
C7—C8—C9—C10	−0.1 (4)	Na1ⁱ—O2W—Na1—O2Wⁱ	−1.91 (12)
O1—C9—C10—C5	−179.7 (2)	Na1ⁱ—O2W—Na1—O4W	169.58 (8)
C8—C9—C10—C5	0.2 (4)	Na1ⁱ—O2W—Na1—Na2	−150.51 (7)
O1—C9—C10—C4	−0.7 (4)	Na2—O4W—Na1—O3W	0.99 (9)
C8—C9—C10—C4	179.2 (3)	Na2—O4W—Na1—O1W	−176.33 (9)
C6—C5—C10—C9	−0.2 (4)	Na2—O4W—Na1—O12	−86.62 (9)
C6—C5—C10—C4	−179.1 (3)	Na2—O4W—Na1—O2Wⁱ	127.7 (4)
C3—C4—C10—C9	−1.4 (4)	Na2—O4W—Na1—O2W	87.60 (9)
C3—C4—C10—C5	177.5 (3)	Na2—O4W—Na1—Na1ⁱ	96.23 (7)
O1—C2—O12—Na1	−163.33 (18)	Na1—O4W—Na2—O5W	−33.5 (6)
C3—C2—O12—Na1	18.6 (4)	Na1—O4W—Na2—O6W	164.49 (8)
C21—O13—C14—O24	−177.8 (2)	Na1—O4W—Na2—O24	−84.88 (8)
C21—O13—C14—C15	2.8 (4)	Na1—O4W—Na2—O3W	−0.91 (8)
O24—C14—C15—C16	179.9 (3)	Na1—O4W—Na2—O6Wⁱⁱ	79.95 (8)
O13—C14—C15—C16	−0.8 (4)	Na1—O4W—Na2—Na2ⁱⁱ	119.96 (7)
C14—C15—C16—C22	−1.5 (4)	Na2ⁱⁱ—O6W—Na2—O4W	−85.92 (9)
C22—C17—C18—C19	0.0 (4)	Na2ⁱⁱ—O6W—Na2—O5W	97.29 (9)
C17—C18—C19—O23	−180.0 (3)	Na2ⁱⁱ—O6W—Na2—O24	−175.72 (7)
C17—C18—C19—C20	−0.2 (4)	Na2ⁱⁱ—O6W—Na2—O3W	31.5 (4)
O23—C19—C20—C21	−179.9 (3)	Na2ⁱⁱ—O6W—Na2—O6Wⁱⁱ	−0.27 (12)
C18—C19—C20—C21	0.3 (4)	Na2ⁱⁱ—O6W—Na2—Na1	−66.35 (14)
C14—O13—C21—C20	177.6 (2)	C14—O24—Na2—O4W	−127.3 (3)
C14—O13—C21—C22	−2.6 (4)	C14—O24—Na2—O5W	60.7 (3)
C19—C20—C21—O13	179.6 (2)	C14—O24—Na2—O6W	−23.3 (3)
C19—C20—C21—C22	−0.2 (4)	C14—O24—Na2—O3W	149.3 (3)
O13—C21—C22—C17	−179.8 (2)	C14—O24—Na2—O6Wⁱⁱ	172.1 (3)
C20—C21—C22—C17	0.0 (4)	C14—O24—Na2—Na1	−171.5 (3)
O13—C21—C22—C16	0.3 (4)	C14—O24—Na2—Na2ⁱⁱ	−30.4 (3)
C20—C21—C22—C16	−179.9 (3)	Na1—O3W—Na2—O4W	1.01 (9)
C18—C17—C22—C21	0.1 (4)	Na1—O3W—Na2—O5W	175.44 (10)
C18—C17—C22—C16	−180.0 (3)	Na1—O3W—Na2—O6W	−119.2 (3)
C15—C16—C22—C21	1.7 (4)	Na1—O3W—Na2—O24	86.13 (9)
C15—C16—C22—C17	−178.2 (3)	Na1—O3W—Na2—O6Wⁱⁱ	−87.11 (9)
O13—C14—O24—Na2	171.97 (17)	Na1—O3W—Na2—Na2ⁱⁱ	−94.02 (7)
C15—C14—O24—Na2	−8.7 (4)	O3W—Na1—Na2—O4W	−178.56 (12)
C33—O25—C26—O36	−179.6 (3)	O1W—Na1—Na2—O4W	4.58 (11)
C33—O25—C26—C27	0.0 (4)	O12—Na1—Na2—O4W	88.33 (10)
O36—C26—C27—C28	179.9 (3)	O2Wⁱ—Na1—Na2—O4W	−160.37 (15)
O25—C26—C27—C28	0.4 (5)	O2W—Na1—Na2—O4W	−86.36 (10)
C26—C27—C28—C34	−0.7 (5)	Na1ⁱ—Na1—Na2—O4W	−109.16 (9)
C34—C29—C30—C31	−0.7 (5)	O3W—Na1—Na2—O5W	−5.73 (12)
C29—C30—C31—O35	−178.9 (3)	O1W—Na1—Na2—O5W	177.41 (11)
C29—C30—C31—C32	1.0 (4)	O12—Na1—Na2—O5W	−98.84 (11)
O35—C31—C32—C33	179.4 (3)	O2Wⁱ—Na1—Na2—O5W	12.46 (16)
C30—C31—C32—C33	−0.5 (4)	O2W—Na1—Na2—O5W	86.47 (11)
C31—C32—C33—O25	179.9 (2)	O4W—Na1—Na2—O5W	172.83 (13)
C31—C32—C33—C34	−0.2 (4)	Na1ⁱ—Na1—Na2—O5W	63.67 (10)
C26—O25—C33—C32	179.8 (3)	O3W—Na1—Na2—O6W	153.64 (15)
C26—O25—C33—C34	−0.1 (4)	O1W—Na1—Na2—O6W	−23.23 (16)
C32—C33—C34—C29	0.4 (4)	O12—Na1—Na2—O6W	60.52 (13)
O25—C33—C34—C29	−179.6 (3)	O2Wⁱ—Na1—Na2—O6W	171.83 (15)
C32—C33—C34—C28	179.9 (3)	O2W—Na1—Na2—O6W	−114.17 (13)
O25—C33—C34—C28	−0.2 (4)	O4W—Na1—Na2—O6W	−27.80 (14)
C30—C29—C34—C33	0.0 (4)	Na1ⁱ—Na1—Na2—O6W	−136.96 (11)
C30—C29—C34—C28	−179.4 (3)	O3W—Na1—Na2—O24	−88.79 (10)
C27—C28—C34—C33	0.6 (4)	O1W—Na1—Na2—O24	94.34 (10)
C27—C28—C34—C29	180.0 (3)	O12—Na1—Na2—O24	178.09 (8)
C45—O37—C38—O48	−179.2 (3)	O2Wⁱ—Na1—Na2—O24	−70.60 (13)
C45—O37—C38—C39	0.9 (4)	O2W—Na1—Na2—O24	3.40 (8)
O48—C38—C39—C40	179.9 (3)	O4W—Na1—Na2—O24	89.77 (10)
O37—C38—C39—C40	−0.2 (4)	Na1ⁱ—Na1—Na2—O24	−19.40 (7)
C38—C39—C40—C46	−0.2 (5)	O1W—Na1—Na2—O3W	−176.86 (13)
C46—C41—C42—C43	0.8 (5)	O12—Na1—Na2—O3W	−93.11 (10)
C41—C42—C43—O47	−179.4 (3)	O2Wⁱ—Na1—Na2—O3W	18.19 (14)
C41—C42—C43—C44	0.5 (4)	O2W—Na1—Na2—O3W	92.20 (10)
O47—C43—C44—C45	178.8 (3)	O4W—Na1—Na2—O3W	178.56 (12)
C42—C43—C44—C45	−1.2 (4)	Na1ⁱ—Na1—Na2—O3W	69.40 (9)
C43—C44—C45—O37	−179.1 (2)	O3W—Na1—Na2—O6Wⁱⁱ	86.26 (10)
C43—C44—C45—C46	0.6 (4)	O1W—Na1—Na2—O6Wⁱⁱ	−90.60 (10)
C38—O37—C45—C44	178.6 (3)	O12—Na1—Na2—O6Wⁱⁱ	−6.85 (8)
C38—O37—C45—C46	−1.1 (4)	O2Wⁱ—Na1—Na2—O6Wⁱⁱ	104.45 (13)
C44—C45—C46—C41	0.7 (4)	O2W—Na1—Na2—O6Wⁱⁱ	178.46 (8)
O37—C45—C46—C41	−179.6 (3)	O4W—Na1—Na2—O6Wⁱⁱ	−95.18 (10)
C44—C45—C46—C40	−179.0 (3)	Na1ⁱ—Na1—Na2—O6Wⁱⁱ	155.66 (6)
O37—C45—C46—C40	0.7 (4)	O3W—Na1—Na2—Na2ⁱⁱ	108.28 (9)
C42—C41—C46—C45	−1.4 (4)	O1W—Na1—Na2—Na2ⁱⁱ	−68.58 (9)
C42—C41—C46—C40	178.3 (3)	O12—Na1—Na2—Na2ⁱⁱ	15.17 (7)
C39—C40—C46—C45	−0.1 (4)	O2Wⁱ—Na1—Na2—Na2ⁱⁱ	126.47 (12)
C39—C40—C46—C41	−179.7 (3)	O2W—Na1—Na2—Na2ⁱⁱ	−159.52 (6)
Na2—O3W—Na1—O1W	13.9 (6)	O4W—Na1—Na2—Na2ⁱⁱ	−73.16 (8)
Na2—O3W—Na1—O12	82.74 (9)	Na1ⁱ—Na1—Na2—Na2ⁱⁱ	177.68 (3)
Na2—O3W—Na1—O2Wⁱ	−169.90 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8W—H8B···O47ⁱⁱ	0.91 (4)	1.78 (4)	2.658 (3)	162 (4)
O8W—H8A···O1Wⁱⁱⁱ	0.83 (4)	2.02 (4)	2.809 (3)	159 (4)
O7W—H7A···O12^iv	0.77 (4)	2.43 (4)	3.068 (3)	141 (4)
O7W—H7B···O35	0.94 (4)	1.73 (4)	2.668 (3)	180 (5)
O6W—H6B···O12ⁱⁱ	0.84 (4)	2.09 (4)	2.913 (3)	165 (3)
O6W—H6A···O35ⁱⁱ	0.84 (4)	2.06 (4)	2.843 (3)	156 (3)
O5W—H5B···O47ⁱⁱ	0.86 (4)	1.96 (4)	2.799 (3)	167 (4)
O5W—H5A···O7Wⁱⁱ	0.76 (4)	2.07 (4)	2.819 (3)	171 (4)
O4W—H4B···O47^v	0.86 (4)	1.92 (4)	2.776 (3)	171 (3)
O4W—H4A···O7W^vi	0.89 (4)	1.98 (4)	2.854 (3)	164 (3)
O3W—H3B···O8W	0.83 (4)	1.98 (4)	2.796 (3)	170 (3)
O3W—H3A···O35	0.82 (4)	2.01 (4)	2.804 (3)	164 (3)
O2W—H2B···O24	0.83 (4)	2.20 (4)	2.932 (3)	148 (3)
O2W—H2A···O47^v	0.89 (4)	2.01 (4)	2.870 (3)	164 (3)
O1W—H1B···O8W^vi	0.84 (4)	2.08 (4)	2.897 (4)	164 (3)
O1W—H1A···O35^vi	0.91 (4)	1.83 (4)	2.739 (3)	174 (3)
O23—H23···O36^vii	0.84	1.83	2.664 (3)	175
O11—H11···O48^viii	0.84	1.81	2.641 (3)	173

Symmetry codes: (ii) −x+1, y, −z+1/2; (iii) −x, y−1, −z+1/2; (iv) x, y−1, z; (v) −x+1, y+1, −z+1/2; (vi) x, y+1, z; (vii) x, −y+1, z+1/2; (viii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Na(C₉H₆O₃)(H₂O)₃](C₉H₅O₃)·H₂O
M_r	418.32
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	173
a, b, c (Å)	11.7803 (5), 7.6462 (3), 42.3249 (17)
β (°)	102.184 (1)
V (Å³)	3726.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.46 × 0.44 × 0.39

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.938, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	16682, 7251, 5790
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.153, 1.13
No. of reflections	7251
No. of parameters	573
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.31

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8W—H8B···O47ⁱ	0.91 (4)	1.78 (4)	2.658 (3)	162 (4)
O8W—H8A···O1Wⁱⁱ	0.83 (4)	2.02 (4)	2.809 (3)	159 (4)
O7W—H7A···O12ⁱⁱⁱ	0.77 (4)	2.43 (4)	3.068 (3)	141 (4)
O7W—H7B···O35	0.94 (4)	1.73 (4)	2.668 (3)	180 (5)
O6W—H6B···O12ⁱ	0.84 (4)	2.09 (4)	2.913 (3)	165 (3)
O6W—H6A···O35ⁱ	0.84 (4)	2.06 (4)	2.843 (3)	156 (3)
O5W—H5B···O47ⁱ	0.86 (4)	1.96 (4)	2.799 (3)	167 (4)
O5W—H5A···O7Wⁱ	0.76 (4)	2.07 (4)	2.819 (3)	171 (4)
O4W—H4B···O47^iv	0.86 (4)	1.92 (4)	2.776 (3)	171 (3)
O4W—H4A···O7W^v	0.89 (4)	1.98 (4)	2.854 (3)	164 (3)
O3W—H3B···O8W	0.83 (4)	1.98 (4)	2.796 (3)	170 (3)
O3W—H3A···O35	0.82 (4)	2.01 (4)	2.804 (3)	164 (3)
O2W—H2B···O24	0.83 (4)	2.20 (4)	2.932 (3)	148 (3)
O2W—H2A···O47^iv	0.89 (4)	2.01 (4)	2.870 (3)	164 (3)
O1W—H1B···O8W^v	0.84 (4)	2.08 (4)	2.897 (4)	164 (3)
O1W—H1A···O35^v	0.91 (4)	1.83 (4)	2.739 (3)	174 (3)
O23—H23···O36^vi	0.84	1.83	2.664 (3)	174.5
O11—H11···O48^vii	0.84	1.81	2.641 (3)	172.5

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x, y−1, −z+1/2; (iii) x, y−1, z; (iv) −x+1, y+1, −z+1/2; (v) x, y+1, z; (vi) x, −y+1, z+1/2; (vii) −x+1, −y+1, −z.

Footnotes

‡Permanent address: Department of Pharmacology, Shantou University Medical College, Shantou 515041, People's Republic of China.

Acknowledgements

This work was supported by a grant from the National Natural Science Foundation of China (No. 30973922).

References

Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Egan, D., O'Kennedy, R., Moran, E., Cox, D., Prosser, E. & Thornes, R. D. (1990). Drug Metab. Rev. 22, 503–529. CrossRef CAS PubMed Web of Science Google Scholar
Nath, M., Jairath, R., Eng, G., Song, X. & Kumar, A. (2005). J. Organomet. Chem. 690, 134–144. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Toyama, D. O., Marangoni, S., Diz-Filho, E. B., Oliveira, S. C. & Toyama, M. H. (2009). Toxicon, 53, 417–426. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 66| Part 7| July 2010| Pages m834-m835

doi:10.1107/S160053681002341X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[[[aqua(7-hy­droxy-2H-1-benzo­pyran-2-one)sodium]-di-μ-aqua] 2-oxo-2H-1-benzo­pyran-7-olate monohydrate]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

metal-organic compounds

catena-Poly[[[aqua(7-hydroxy-2H-1-benzopyran-2-one)sodium]-di-μ-aqua] 2-oxo-2H-1-benzopyran-7-olate monohydrate]