catena-Poly[[[aqua­[3-(3-hy­droxy­phen­yl)prop-2-enoato]samarium(III)]-bis­[μ2-3-(3-hy­droxy­phen­yl)prop-2-enoato]] monohydrate]

Guo, J.; Wen, Y.-H.

doi:10.1107/S1600536812013724

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m543-m544

doi:10.1107/S1600536812013724

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catena-Poly[[[aqua[3-(3-hydroxyphenyl)prop-2-enoato]samarium(III)]-bis[μ₂-3-(3-hydroxyphenyl)prop-2-enoato]] monohydrate]

Jing-ke Guo ^a and Yi-Hang Wen ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, College of Chemistry and Life Science, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: wyh@zjnu.edu.cn

(Received 29 December 2011; accepted 29 March 2012; online 4 April 2012)

The title Sm^III compound, {[Sm(C₉H₇O₃)₃(H₂O)]·H₂O}_n, was obtained under hydrothermal conditions. Its structure is isotypic with the analogous Eu complex. The latter was reported incorrectly in space group P1 by Yan et al. [J. Mol. Struct. (2008), 891, 298–304]. This was corrected by Marsh [Acta Cryst. B65, 782–783] to P-1. The Sm^III ion is nine-coordinated by O atoms from one coordinating water molecule and the remaining ones from the 3-(3-hydroxyphenyl)prop-2-enoatate anions (one bidentate, two bidentate and bridging, two monodentate bridging), leading to a distorted tricapped trigonal–prismatic coordination polyhedron surrounded by solvent water molecules. In the crystal, extensive intermolecular O—H⋯O hydrogen-bonding interactions and π–π interactions [centroid–centroid separation = 3.9393 (1) Å] lead to the formation of a three-dimensional supramolecular network.

Related literature

For the isotypic Eu structure, see: Yan et al. (2008 ) and for the corrected space-group assignment, see: Marsh (2009 ). For related structures, see: Niu et al. (2008 ); Tang et al. (2009 ); Wang & Feng (2010 ); Xue et al. (2007 ); Ye et al. (2005 ).

Experimental

Crystal data

[Sm(C₉H₇O₃)₃(H₂O)]·H₂O
M_r = 675.82
Triclinic, $[P \overline 1]$
a = 7.9411 (1) Å
b = 13.0312 (2) Å
c = 13.6564 (2) Å
α = 97.356 (1)°
β = 97.120 (1)°
γ = 103.739 (1)°
V = 1343.87 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.25 mm⁻¹
T = 296 K
0.52 × 0.24 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.53, T_max = 0.71
17958 measured reflections
4722 independent reflections
4590 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.014
wR(F²) = 0.037
S = 1.04
4722 reflections
373 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O5ⁱ	0.82 (2)	2.02 (2)	2.8183 (18)	163 (2)
O3—H3⋯O8ⁱⁱ	0.91 (2)	1.76 (2)	2.6692 (19)	176 (3)
O6—H6⋯O7ⁱⁱⁱ	0.92 (2)	1.78 (2)	2.7005 (19)	174 (3)
O2W—H2WA⋯O9^iv	0.84 (2)	2.15 (2)	2.947 (4)	158 (3)
O1W—H1WB⋯O2W^v	0.83 (2)	1.86 (2)	2.688 (2)	175 (2)
O2W—H2WB⋯O3^vi	0.81 (2)	1.98 (2)	2.790 (3)	173 (4)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y, z+1; (iii) x+1, y+1, z; (iv) -x+1, -y+1, -z; (v) -x+1, -y+1, -z+1; (vi) x, y, z-1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013724/zj2052sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013724/zj2052Isup2.hkl

checkCIF report

Comment top

It is well known that metal and appropriate ligand are the keys for construction of metal-organic frameworks. Here we choose 3-hydroxycinnamic acid as a ligand due to its unique ability to form stable chelates in diverse coordination modes. Reserches on the compounds containing metal ions and 3-hydroxycinnamic acid have been reported (Niu et al. (2008); Xue et al.(2007); Ye et al.(2005)). Hererin we report a Sm^III compound, Sm(C₉H₇O₃)₃(H₂O).(H₂O), derived from 3-hydroxycinnamic acid (H₂L),which is not the first rare-earth complex of this ligand. It is isostructural to the Eu complex, Firstly wrongly in P1 by Yan et al., in 2008, this was then corrected by Marsh to P-1 in 2009.

As is shown in Fig. 1, the structrue contains only one nine-coordinated Sm^(III) ions which is coordinated by eight oxygen atoms from carboxylate groups in four 3-hydroxyphenyl anions and one oxygen atom from the water molecule, leading to a distored tricapped trigonal prism structure surrounded by solvent H₂O molecule.

In the structure,the 3-hydroxycinnamic acids coordinate via three chelating carboxylate groups and two oxygen atoms of another two carboxylate groups bridging two Sm^(III) ions [Sm—O distances in the range of 2.3695 (11) and 2.5861 (11) Å], to form a one-dimensional chain with Sm···Sm 4.0887 (1) Å. Furthermore,the oxygen atom in the coordinated water molecule [Sm—O distance 2.4517 (13) Å] completes the nine-coordinated configuration of Sm. In addition,there are one lattice H₂O molecule in the crystal structure. Intermolecular O—H···O and C—H···O hydrogen bonds connect the molecules to form a three-dimensional supramolecular skeleton (Fig. 2).

Related literature top

For the isotypic Eu compound, see: Yan et al. (2008) and for the corrected space-group assignment, see: Marsh (2009). For related structures, see: Niu et al. (2008); Tang et al. (2009); Wang & Feng (2010); Xue et al. (2007); Ye et al. (2005). AUTHOR: scheme cropped at top. Please resend

Experimental top

A mixture of Sm(NO₃)₃(0.1682 g, 0.5 mmol),3-hydroxycinnamic acid (0.2462 g, 1.5 mmol) and 4,4-bipyridine (0.2343 g, 1.5 mmol) was dissolved in a 16 mL EtOH/H₂O(v/v,1:15) and then sealed in a 25 ml stainless steel reactor with a telflon liner and heated at 413 K for 72 h, and then cooled to room temperature over 3 days. Then, the reactor was cooled to room temperature at a speed of 5 degrees per hour. Yellow single crystals of title compound were obtained by slow evaporation of the filtrate over a few days.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) -x,-y + 1,-z + 1; (ii) -x + 1,-y + 1,-z + 1.]
	Fig. 2. View of the supramolecular network conneted by hydrogen bonds.

catena-Poly[[[aqua[3-(3-hydroxyphenyl)prop-2-enoato]samarium(III)]- bis[µ₂-3-(3-hydroxyphenyl)prop-2-enoato]] monohydrate] top

Crystal data top

[Sm(C₉H₇O₃)₃(H₂O)]·H₂O	Z = 2
M_r = 675.82	F(000) = 674
Triclinic, P1	D_x = 1.670 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9411 (1) Å	Cell parameters from 9871 reflections
b = 13.0312 (2) Å	θ = 1.6–25.0°
c = 13.6564 (2) Å	µ = 2.25 mm⁻¹
α = 97.356 (1)°	T = 296 K
β = 97.120 (1)°	Block, yellow
γ = 103.739 (1)°	0.52 × 0.24 × 0.15 mm
V = 1343.87 (3) Å³

Data collection top

Bruker APEXII area-detector diffractometer	4722 independent reflections
Radiation source: fine-focus sealed tube	4590 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.53, T_max = 0.71	k = −15→15
17958 measured reflections	l = −16→16

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)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.037	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0243P)² + 0.3656P] where P = (F_o² + 2F_c²)/3
4722 reflections	(Δ/σ)_max = 0.002
373 parameters	Δρ_max = 0.40 e Å⁻³
10 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Sm(C₉H₇O₃)₃(H₂O)]·H₂O	γ = 103.739 (1)°
M_r = 675.82	V = 1343.87 (3) Å³
Triclinic, P1	Z = 2
a = 7.9411 (1) Å	Mo Kα radiation
b = 13.0312 (2) Å	µ = 2.25 mm⁻¹
c = 13.6564 (2) Å	T = 296 K
α = 97.356 (1)°	0.52 × 0.24 × 0.15 mm
β = 97.120 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	4722 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4590 reflections with I > 2σ(I)
T_min = 0.53, T_max = 0.71	R_int = 0.016
17958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.014	10 restraints
wR(F²) = 0.037	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.40 e Å⁻³
4722 reflections	Δρ_min = −0.47 e Å⁻³
373 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Sm1	0.231707 (9)	0.462033 (5)	0.480253 (5)	0.01695 (4)
O1	0.06012 (15)	0.55519 (9)	0.59671 (8)	0.0240 (2)
O1W	0.07151 (18)	0.32289 (11)	0.56401 (11)	0.0324 (3)
H1WA	−0.034 (2)	0.318 (2)	0.5643 (17)	0.049*
H1WB	0.109 (3)	0.312 (2)	0.6205 (14)	0.049*
O2	0.32583 (16)	0.54888 (12)	0.65526 (9)	0.0349 (3)
O2W	0.7925 (2)	0.70266 (18)	0.25319 (14)	0.0629 (5)
H2WA	0.786 (4)	0.7600 (17)	0.232 (3)	0.094*
H2WB	0.697 (3)	0.661 (2)	0.232 (3)	0.094*
O3	0.4554 (2)	0.56809 (15)	1.19165 (12)	0.0515 (4)
H3	0.401 (3)	0.5246 (19)	1.2314 (18)	0.062*
O4	0.51185 (15)	0.59885 (9)	0.47391 (9)	0.0240 (3)
O5	0.26831 (15)	0.64608 (9)	0.43899 (10)	0.0278 (3)
O6	1.0331 (2)	1.09500 (12)	0.39523 (14)	0.0506 (4)
H6	1.080 (3)	1.1627 (15)	0.382 (2)	0.061*
O7	0.19076 (17)	0.29241 (9)	0.36232 (9)	0.0306 (3)
O8	0.28389 (16)	0.44152 (9)	0.30584 (9)	0.0259 (3)
O9	0.3333 (5)	0.1288 (2)	−0.16532 (17)	0.1181 (11)
H9	0.351 (6)	0.077 (3)	−0.215 (3)	0.142*
C1	0.3318 (3)	0.59470 (16)	1.12695 (14)	0.0358 (4)
C2	0.1850 (3)	0.62021 (18)	1.15591 (15)	0.0437 (5)
H2A	0.1672	0.6218	1.2221	0.052*
C3	0.0638 (3)	0.6435 (2)	1.08592 (16)	0.0479 (6)
H3A	−0.0346	0.6618	1.1056	0.057*
C4	0.0877 (3)	0.63986 (18)	0.98720 (15)	0.0401 (5)
H4A	0.0039	0.6541	0.9406	0.048*
C5	0.2359 (3)	0.61510 (15)	0.95721 (14)	0.0313 (4)
C6	0.3595 (3)	0.59493 (16)	1.02878 (14)	0.0349 (4)
H6A	0.4621	0.5814	1.0104	0.042*
C7	0.2629 (2)	0.60020 (16)	0.85277 (14)	0.0320 (4)
H7A	0.3726	0.5922	0.8417	0.038*
C8	0.1498 (2)	0.59684 (16)	0.77289 (13)	0.0306 (4)
H8A	0.0447	0.6140	0.7811	0.037*
C9	0.1830 (2)	0.56691 (14)	0.67091 (13)	0.0237 (4)
C10	0.8553 (3)	1.07639 (15)	0.38269 (15)	0.0351 (4)
C11	0.7683 (3)	1.14997 (15)	0.35253 (16)	0.0406 (5)
H11A	0.8315	1.2160	0.3411	0.049*
C12	0.5879 (3)	1.12497 (16)	0.33946 (18)	0.0457 (5)
H12A	0.5299	1.1749	0.3196	0.055*
C13	0.4906 (3)	1.02652 (16)	0.35534 (17)	0.0395 (5)
H13A	0.3686	1.0104	0.3454	0.047*
C14	0.5770 (3)	0.95222 (14)	0.38628 (14)	0.0305 (4)
C15	0.7603 (3)	0.97840 (14)	0.40027 (15)	0.0329 (4)
H15A	0.8194	0.9296	0.4216	0.040*
C16	0.4745 (3)	0.84864 (14)	0.40343 (14)	0.0306 (4)
H16A	0.3529	0.8359	0.3920	0.037*
C17	0.5399 (2)	0.77163 (14)	0.43369 (14)	0.0291 (4)
H17A	0.6614	0.7836	0.4458	0.035*
C18	0.4330 (2)	0.66875 (13)	0.44924 (12)	0.0214 (3)
C19	0.2960 (5)	0.0830 (2)	−0.0827 (2)	0.0676 (8)
C20	0.2780 (5)	−0.0240 (2)	−0.0819 (2)	0.0729 (9)
H20A	0.2905	−0.0681	−0.1383	0.087*
C21	0.2415 (5)	−0.0653 (2)	0.0023 (3)	0.0786 (10)
H21A	0.2308	−0.1377	0.0036	0.094*
C22	0.2202 (4)	−0.0002 (2)	0.0858 (2)	0.0643 (8)
H22A	0.1926	−0.0294	0.1422	0.077*
C23	0.2398 (3)	0.10820 (18)	0.08566 (17)	0.0436 (5)
C24	0.2779 (4)	0.1496 (2)	0.00018 (18)	0.0572 (7)
H24A	0.2912	0.2222	−0.0014	0.069*
C25	0.2225 (3)	0.17526 (16)	0.17687 (15)	0.0390 (5)
H25A	0.1776	0.1391	0.2262	0.047*
C26	0.2632 (3)	0.28090 (15)	0.19707 (14)	0.0319 (4)
H26A	0.3052	0.3196	0.1486	0.038*
C27	0.2452 (2)	0.34016 (14)	0.29289 (13)	0.0241 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sm1	0.01437 (6)	0.01882 (5)	0.01808 (6)	0.00429 (3)	0.00325 (3)	0.00391 (3)
O1	0.0194 (6)	0.0320 (6)	0.0198 (6)	0.0078 (5)	0.0009 (5)	0.0018 (5)
O1W	0.0274 (7)	0.0365 (7)	0.0393 (8)	0.0103 (6)	0.0122 (6)	0.0173 (6)
O2	0.0209 (6)	0.0605 (9)	0.0234 (6)	0.0171 (6)	0.0007 (5)	−0.0023 (6)
O2W	0.0519 (11)	0.0872 (14)	0.0500 (11)	0.0134 (10)	0.0081 (8)	0.0216 (10)
O3	0.0422 (9)	0.0771 (11)	0.0373 (8)	0.0086 (8)	0.0032 (7)	0.0328 (8)
O4	0.0185 (6)	0.0208 (6)	0.0340 (7)	0.0063 (5)	0.0027 (5)	0.0084 (5)
O5	0.0190 (6)	0.0254 (6)	0.0420 (7)	0.0076 (5)	0.0066 (5)	0.0109 (5)
O6	0.0413 (9)	0.0343 (8)	0.0739 (12)	−0.0010 (7)	0.0068 (8)	0.0225 (8)
O7	0.0377 (7)	0.0244 (6)	0.0275 (7)	0.0027 (5)	0.0086 (6)	0.0033 (5)
O8	0.0275 (6)	0.0257 (6)	0.0250 (6)	0.0059 (5)	0.0077 (5)	0.0046 (5)
O9	0.224 (3)	0.0984 (18)	0.0477 (12)	0.057 (2)	0.0579 (17)	0.0054 (12)
C1	0.0355 (11)	0.0413 (11)	0.0270 (10)	0.0019 (8)	0.0010 (8)	0.0113 (8)
C2	0.0549 (14)	0.0517 (13)	0.0255 (10)	0.0117 (10)	0.0127 (10)	0.0080 (9)
C3	0.0507 (14)	0.0636 (15)	0.0366 (12)	0.0248 (11)	0.0167 (10)	0.0062 (10)
C4	0.0420 (12)	0.0539 (12)	0.0298 (10)	0.0225 (10)	0.0066 (9)	0.0067 (9)
C5	0.0336 (10)	0.0350 (10)	0.0244 (9)	0.0083 (8)	0.0038 (8)	0.0033 (7)
C6	0.0297 (10)	0.0445 (11)	0.0302 (10)	0.0073 (8)	0.0038 (8)	0.0095 (8)
C7	0.0271 (9)	0.0444 (11)	0.0255 (9)	0.0113 (8)	0.0050 (8)	0.0039 (8)
C8	0.0260 (9)	0.0455 (11)	0.0231 (9)	0.0159 (8)	0.0047 (8)	0.0022 (8)
C9	0.0225 (9)	0.0256 (8)	0.0217 (9)	0.0056 (7)	0.0024 (7)	0.0017 (7)
C10	0.0425 (12)	0.0257 (9)	0.0333 (10)	0.0021 (8)	0.0039 (9)	0.0059 (8)
C11	0.0544 (13)	0.0226 (9)	0.0425 (12)	0.0029 (9)	0.0067 (10)	0.0115 (8)
C12	0.0588 (15)	0.0289 (10)	0.0549 (14)	0.0175 (10)	0.0061 (11)	0.0179 (10)
C13	0.0418 (12)	0.0326 (10)	0.0466 (12)	0.0125 (9)	0.0050 (10)	0.0121 (9)
C14	0.0398 (11)	0.0236 (9)	0.0287 (9)	0.0075 (8)	0.0070 (8)	0.0061 (7)
C15	0.0391 (11)	0.0235 (9)	0.0373 (10)	0.0069 (8)	0.0053 (9)	0.0116 (8)
C16	0.0304 (10)	0.0258 (9)	0.0370 (10)	0.0069 (7)	0.0072 (8)	0.0089 (8)
C17	0.0239 (9)	0.0256 (9)	0.0389 (10)	0.0052 (7)	0.0087 (8)	0.0086 (8)
C18	0.0215 (9)	0.0216 (8)	0.0222 (8)	0.0068 (6)	0.0047 (7)	0.0036 (6)
C19	0.096 (2)	0.0696 (18)	0.0382 (14)	0.0266 (16)	0.0186 (14)	−0.0042 (12)
C20	0.095 (2)	0.0618 (18)	0.0569 (18)	0.0250 (16)	0.0176 (16)	−0.0221 (14)
C21	0.116 (3)	0.0413 (14)	0.074 (2)	0.0186 (15)	0.0223 (19)	−0.0111 (14)
C22	0.091 (2)	0.0405 (13)	0.0580 (16)	0.0123 (13)	0.0192 (15)	−0.0024 (12)
C23	0.0502 (13)	0.0402 (12)	0.0371 (12)	0.0117 (10)	0.0068 (10)	−0.0057 (9)
C24	0.086 (2)	0.0462 (13)	0.0402 (13)	0.0215 (13)	0.0153 (13)	−0.0018 (10)
C25	0.0472 (12)	0.0391 (11)	0.0306 (10)	0.0121 (9)	0.0084 (9)	0.0021 (8)
C26	0.0350 (10)	0.0364 (10)	0.0251 (9)	0.0112 (8)	0.0072 (8)	0.0019 (8)
C27	0.0175 (8)	0.0307 (9)	0.0240 (9)	0.0070 (7)	0.0024 (7)	0.0030 (7)

Geometric parameters (Å, º) top

Sm1—O1ⁱ	2.3695 (11)	C5—C6	1.392 (3)
Sm1—O4ⁱⁱ	2.3973 (11)	C5—C7	1.464 (3)
Sm1—O1W	2.4517 (13)	C6—H6A	0.9300
Sm1—O2	2.4524 (12)	C7—C8	1.313 (3)
Sm1—O8	2.4598 (12)	C7—H7A	0.9300
Sm1—O7	2.4905 (12)	C8—C9	1.470 (2)
Sm1—O5	2.4919 (12)	C8—H8A	0.9300
Sm1—O4	2.5176 (11)	C10—C11	1.382 (3)
Sm1—O1	2.5861 (11)	C10—C15	1.387 (3)
Sm1—C27	2.8616 (17)	C11—C12	1.375 (3)
Sm1—C9	2.8959 (17)	C11—H11A	0.9300
Sm1—C18	2.8991 (16)	C12—C13	1.390 (3)
O1—C9	1.283 (2)	C12—H12A	0.9300
O1—Sm1ⁱ	2.3695 (11)	C13—C14	1.391 (3)
O1W—H1WA	0.824 (15)	C13—H13A	0.9300
O1W—H1WB	0.834 (16)	C14—C15	1.397 (3)
O2—C9	1.249 (2)	C14—C16	1.465 (2)
O2W—H2WA	0.844 (17)	C15—H15A	0.9300
O2W—H2WB	0.814 (17)	C16—C17	1.322 (3)
O3—C1	1.374 (3)	C16—H16A	0.9300
O3—H3	0.906 (17)	C17—C18	1.463 (2)
O4—C18	1.278 (2)	C17—H17A	0.9300
O4—Sm1ⁱⁱ	2.3973 (11)	C19—C20	1.369 (4)
O5—C18	1.256 (2)	C19—C24	1.379 (3)
O6—C10	1.360 (3)	C20—C21	1.365 (5)
O6—H6	0.923 (17)	C20—H20A	0.9300
O7—C27	1.264 (2)	C21—C22	1.384 (4)
O8—C27	1.267 (2)	C21—H21A	0.9300
O9—C19	1.374 (4)	C22—C23	1.384 (3)
O9—H9	0.944 (19)	C22—H22A	0.9300
C1—C2	1.375 (3)	C23—C24	1.384 (4)
C1—C6	1.385 (3)	C23—C25	1.468 (3)
C2—C3	1.385 (3)	C24—H24A	0.9300
C2—H2A	0.9300	C25—C26	1.321 (3)
C3—C4	1.381 (3)	C25—H25A	0.9300
C3—H3A	0.9300	C26—C27	1.473 (2)
C4—C5	1.387 (3)	C26—H26A	0.9300
C4—H4A	0.9300

O1ⁱ—Sm1—O4ⁱⁱ	155.55 (4)	C1—C2—H2A	120.2
O1ⁱ—Sm1—O1W	79.70 (5)	C3—C2—H2A	120.2
O4ⁱⁱ—Sm1—O1W	87.34 (4)	C4—C3—C2	120.7 (2)
O1ⁱ—Sm1—O2	119.15 (4)	C4—C3—H3A	119.7
O4ⁱⁱ—Sm1—O2	78.18 (4)	C2—C3—H3A	119.7
O1W—Sm1—O2	79.90 (5)	C3—C4—C5	120.3 (2)
O1ⁱ—Sm1—O8	82.67 (4)	C3—C4—H4A	119.9
O4ⁱⁱ—Sm1—O8	88.82 (4)	C5—C4—H4A	119.9
O1W—Sm1—O8	126.86 (4)	C4—C5—C6	118.54 (18)
O2—Sm1—O8	150.00 (4)	C4—C5—C7	123.46 (18)
O1ⁱ—Sm1—O7	81.62 (4)	C6—C5—C7	117.80 (17)
O4ⁱⁱ—Sm1—O7	75.09 (4)	C1—C6—C5	120.92 (19)
O1W—Sm1—O7	75.65 (4)	C1—C6—H6A	119.5
O2—Sm1—O7	144.28 (5)	C5—C6—H6A	119.5
O8—Sm1—O7	52.30 (4)	C8—C7—C5	127.42 (18)
O1ⁱ—Sm1—O5	81.25 (4)	C8—C7—H7A	116.3
O4ⁱⁱ—Sm1—O5	119.02 (4)	C5—C7—H7A	116.3
O1W—Sm1—O5	147.03 (4)	C7—C8—C9	122.50 (17)
O2—Sm1—O5	86.30 (5)	C7—C8—H8A	118.8
O8—Sm1—O5	76.50 (4)	C9—C8—H8A	118.8
O7—Sm1—O5	127.52 (4)	O2—C9—O1	119.34 (15)
O1ⁱ—Sm1—O4	130.35 (4)	O2—C9—C8	121.45 (16)
O4ⁱⁱ—Sm1—O4	67.43 (4)	O1—C9—C8	119.16 (15)
O1W—Sm1—O4	148.72 (4)	O2—C9—Sm1	57.08 (9)
O2—Sm1—O4	77.13 (4)	O1—C9—Sm1	63.25 (8)
O8—Sm1—O4	72.92 (4)	C8—C9—Sm1	167.72 (13)
O7—Sm1—O4	112.86 (4)	O6—C10—C11	122.73 (17)
O5—Sm1—O4	51.62 (4)	O6—C10—C15	117.38 (19)
O1ⁱ—Sm1—O1	67.98 (4)	C11—C10—C15	119.9 (2)
O4ⁱⁱ—Sm1—O1	128.01 (4)	C12—C11—C10	119.62 (18)
O1W—Sm1—O1	73.82 (4)	C12—C11—H11A	120.2
O2—Sm1—O1	51.34 (4)	C10—C11—H11A	120.2
O8—Sm1—O1	140.98 (4)	C11—C12—C13	121.2 (2)
O7—Sm1—O1	139.96 (4)	C11—C12—H12A	119.4
O5—Sm1—O1	74.17 (4)	C13—C12—H12A	119.4
O4—Sm1—O1	106.71 (4)	C12—C13—C14	119.5 (2)
O1ⁱ—Sm1—C27	82.20 (4)	C12—C13—H13A	120.2
O4ⁱⁱ—Sm1—C27	80.18 (5)	C14—C13—H13A	120.2
O1W—Sm1—C27	101.49 (5)	C13—C14—C15	118.97 (18)
O2—Sm1—C27	158.23 (5)	C13—C14—C16	119.57 (18)
O8—Sm1—C27	26.17 (5)	C15—C14—C16	121.46 (17)
O7—Sm1—C27	26.16 (5)	C10—C15—C14	120.72 (19)
O5—Sm1—C27	102.28 (5)	C10—C15—H15A	119.6
O4—Sm1—C27	92.42 (4)	C14—C15—H15A	119.6
O1—Sm1—C27	150.18 (4)	C17—C16—C14	125.68 (18)
O1ⁱ—Sm1—C9	93.84 (4)	C17—C16—H16A	117.2
O4ⁱⁱ—Sm1—C9	102.04 (5)	C14—C16—H16A	117.2
O1W—Sm1—C9	72.73 (5)	C16—C17—C18	124.04 (17)
O2—Sm1—C9	25.32 (5)	C16—C17—H17A	118.0
O8—Sm1—C9	158.51 (5)	C18—C17—H17A	118.0
O7—Sm1—C9	148.35 (4)	O5—C18—O4	118.84 (15)
O5—Sm1—C9	82.02 (5)	O5—C18—C17	123.16 (16)
O4—Sm1—C9	94.00 (4)	O4—C18—C17	118.00 (15)
O1—Sm1—C9	26.30 (4)	O5—C18—Sm1	58.79 (8)
C27—Sm1—C9	173.57 (5)	O4—C18—Sm1	60.05 (8)
O1ⁱ—Sm1—C18	105.70 (4)	C17—C18—Sm1	178.01 (12)
O4ⁱⁱ—Sm1—C18	93.51 (4)	C20—C19—O9	121.7 (2)
O1W—Sm1—C18	160.17 (5)	C20—C19—C24	121.1 (3)
O2—Sm1—C18	80.89 (5)	O9—C19—C24	117.2 (3)
O8—Sm1—C18	72.97 (4)	C21—C20—C19	119.3 (2)
O7—Sm1—C18	123.71 (4)	C21—C20—H20A	120.3
O5—Sm1—C18	25.53 (4)	C19—C20—H20A	120.3
O4—Sm1—C18	26.09 (4)	C20—C21—C22	120.5 (3)
O1—Sm1—C18	90.30 (4)	C20—C21—H21A	119.7
C27—Sm1—C18	98.18 (5)	C22—C21—H21A	119.7
C9—Sm1—C18	87.75 (5)	C23—C22—C21	120.3 (3)
C9—O1—Sm1ⁱ	155.04 (11)	C23—C22—H22A	119.9
C9—O1—Sm1	90.44 (9)	C21—C22—H22A	119.9
Sm1ⁱ—O1—Sm1	112.02 (4)	C22—C23—C24	118.8 (2)
Sm1—O1W—H1WA	117.4 (17)	C22—C23—C25	118.7 (2)
Sm1—O1W—H1WB	123.4 (17)	C24—C23—C25	122.5 (2)
H1WA—O1W—H1WB	104.8 (19)	C19—C24—C23	119.9 (3)
C9—O2—Sm1	97.61 (10)	C19—C24—H24A	120.0
H2WA—O2W—H2WB	105 (2)	C23—C24—H24A	120.0
C1—O3—H3	109.8 (18)	C26—C25—C23	127.6 (2)
C18—O4—Sm1ⁱⁱ	153.49 (10)	C26—C25—H25A	116.2
C18—O4—Sm1	93.86 (9)	C23—C25—H25A	116.2
Sm1ⁱⁱ—O4—Sm1	112.57 (4)	C25—C26—C27	123.00 (19)
C18—O5—Sm1	95.67 (10)	C25—C26—H26A	118.5
C10—O6—H6	108.7 (17)	C27—C26—H26A	118.5
C27—O7—Sm1	93.54 (10)	O7—C27—O8	119.10 (15)
C27—O8—Sm1	94.92 (10)	O7—C27—C26	121.68 (16)
C19—O9—H9	109 (3)	O8—C27—C26	119.22 (16)
O3—C1—C2	122.80 (18)	O7—C27—Sm1	60.30 (9)
O3—C1—C6	117.30 (19)	O8—C27—Sm1	58.92 (8)
C2—C1—C6	119.90 (19)	C26—C27—Sm1	176.60 (13)
C1—C2—C3	119.56 (19)

O1ⁱ—Sm1—O1—C9	168.85 (12)	O1ⁱ—Sm1—C9—O2	−178.87 (11)
O4ⁱⁱ—Sm1—O1—C9	10.38 (11)	O4ⁱⁱ—Sm1—C9—O2	19.83 (12)
O1W—Sm1—O1—C9	83.64 (10)	O1W—Sm1—C9—O2	103.17 (12)
O2—Sm1—O1—C9	−6.26 (10)	O8—Sm1—C9—O2	−99.16 (16)
O8—Sm1—O1—C9	−147.01 (10)	O7—Sm1—C9—O2	100.89 (13)
O7—Sm1—O1—C9	125.36 (10)	O5—Sm1—C9—O2	−98.27 (11)
O5—Sm1—O1—C9	−104.36 (10)	O4—Sm1—C9—O2	−47.93 (12)
O4—Sm1—O1—C9	−63.72 (10)	O1—Sm1—C9—O2	−168.52 (18)
C27—Sm1—O1—C9	168.52 (10)	C18—Sm1—C9—O2	−73.28 (12)
C18—Sm1—O1—C9	−84.31 (10)	O1ⁱ—Sm1—C9—O1	−10.35 (11)
O1ⁱ—Sm1—O1—Sm1ⁱ	0.0	O4ⁱⁱ—Sm1—C9—O1	−171.66 (9)
O4ⁱⁱ—Sm1—O1—Sm1ⁱ	−158.47 (4)	O1W—Sm1—C9—O1	−88.32 (10)
O1W—Sm1—O1—Sm1ⁱ	−85.21 (6)	O2—Sm1—C9—O1	168.52 (17)
O2—Sm1—O1—Sm1ⁱ	−175.11 (8)	O8—Sm1—C9—O1	69.36 (16)
O8—Sm1—O1—Sm1ⁱ	44.14 (8)	O7—Sm1—C9—O1	−90.60 (13)
O7—Sm1—O1—Sm1ⁱ	−43.49 (8)	O5—Sm1—C9—O1	70.24 (9)
O5—Sm1—O1—Sm1ⁱ	86.80 (5)	O4—Sm1—C9—O1	120.58 (9)
O4—Sm1—O1—Sm1ⁱ	127.43 (5)	C18—Sm1—C9—O1	95.23 (10)
C27—Sm1—O1—Sm1ⁱ	−0.32 (11)	O1ⁱ—Sm1—C9—C8	94.1 (6)
C9—Sm1—O1—Sm1ⁱ	−168.85 (12)	O4ⁱⁱ—Sm1—C9—C8	−67.2 (6)
C18—Sm1—O1—Sm1ⁱ	106.84 (5)	O1W—Sm1—C9—C8	16.2 (6)
O1ⁱ—Sm1—O2—C9	1.29 (13)	O2—Sm1—C9—C8	−87.0 (6)
O4ⁱⁱ—Sm1—O2—C9	−160.19 (12)	O8—Sm1—C9—C8	173.9 (5)
O1W—Sm1—O2—C9	−70.81 (11)	O7—Sm1—C9—C8	13.9 (6)
O8—Sm1—O2—C9	133.68 (11)	O5—Sm1—C9—C8	174.7 (6)
O7—Sm1—O2—C9	−118.04 (12)	O4—Sm1—C9—C8	−134.9 (6)
O5—Sm1—O2—C9	79.13 (11)	O1—Sm1—C9—C8	104.5 (6)
O4—Sm1—O2—C9	130.57 (12)	C18—Sm1—C9—C8	−160.3 (6)
O1—Sm1—O2—C9	6.49 (10)	O6—C10—C11—C12	178.7 (2)
C27—Sm1—O2—C9	−166.51 (12)	C15—C10—C11—C12	−0.5 (3)
C18—Sm1—O2—C9	104.25 (12)	C10—C11—C12—C13	−0.5 (3)
O1ⁱ—Sm1—O4—C18	21.91 (11)	C11—C12—C13—C14	0.8 (3)
O4ⁱⁱ—Sm1—O4—C18	−177.95 (12)	C12—C13—C14—C15	−0.3 (3)
O1W—Sm1—O4—C18	−139.30 (10)	C12—C13—C14—C16	179.75 (19)
O2—Sm1—O4—C18	−95.58 (10)	O6—C10—C15—C14	−178.21 (18)
O8—Sm1—O4—C18	86.05 (10)	C11—C10—C15—C14	1.1 (3)
O7—Sm1—O4—C18	120.58 (9)	C13—C14—C15—C10	−0.7 (3)
O5—Sm1—O4—C18	−0.04 (9)	C16—C14—C15—C10	179.31 (18)
O1—Sm1—O4—C18	−53.10 (10)	C13—C14—C16—C17	−179.3 (2)
C27—Sm1—O4—C18	103.73 (10)	C15—C14—C16—C17	0.7 (3)
C9—Sm1—O4—C18	−76.57 (10)	C14—C16—C17—C18	−179.51 (17)
O1ⁱ—Sm1—O4—Sm1ⁱⁱ	−160.13 (4)	Sm1—O5—C18—O4	−0.08 (16)
O4ⁱⁱ—Sm1—O4—Sm1ⁱⁱ	0.0	Sm1—O5—C18—C17	179.55 (15)
O1W—Sm1—O4—Sm1ⁱⁱ	38.66 (10)	Sm1ⁱⁱ—O4—C18—O5	−175.69 (16)
O2—Sm1—O4—Sm1ⁱⁱ	82.38 (5)	Sm1—O4—C18—O5	0.08 (16)
O8—Sm1—O4—Sm1ⁱⁱ	−96.00 (5)	Sm1ⁱⁱ—O4—C18—C17	4.7 (3)
O7—Sm1—O4—Sm1ⁱⁱ	−61.47 (6)	Sm1—O4—C18—C17	−179.57 (13)
O5—Sm1—O4—Sm1ⁱⁱ	177.91 (7)	Sm1ⁱⁱ—O4—C18—Sm1	−175.8 (3)
O1—Sm1—O4—Sm1ⁱⁱ	124.86 (5)	C16—C17—C18—O5	−3.0 (3)
C27—Sm1—O4—Sm1ⁱⁱ	−78.32 (6)	C16—C17—C18—O4	176.63 (17)
C9—Sm1—O4—Sm1ⁱⁱ	101.38 (6)	O1ⁱ—Sm1—C18—O5	17.26 (11)
C18—Sm1—O4—Sm1ⁱⁱ	177.95 (12)	O4ⁱⁱ—Sm1—C18—O5	−178.03 (10)
O1ⁱ—Sm1—O5—C18	−163.20 (10)	O1W—Sm1—C18—O5	−86.14 (17)
O4ⁱⁱ—Sm1—O5—C18	2.25 (11)	O2—Sm1—C18—O5	−100.60 (10)
O1W—Sm1—O5—C18	141.53 (11)	O8—Sm1—C18—O5	94.28 (10)
O2—Sm1—O5—C18	76.54 (10)	O7—Sm1—C18—O5	107.58 (10)
O8—Sm1—O5—C18	−78.70 (10)	O4—Sm1—C18—O5	−179.92 (16)
O7—Sm1—O5—C18	−90.91 (11)	O1—Sm1—C18—O5	−49.91 (10)
O4—Sm1—O5—C18	0.04 (9)	C27—Sm1—C18—O5	101.40 (10)
O1—Sm1—O5—C18	127.32 (10)	C9—Sm1—C18—O5	−76.10 (10)
C27—Sm1—O5—C18	−83.23 (10)	O1ⁱ—Sm1—C18—O4	−162.82 (9)
C9—Sm1—O5—C18	101.64 (10)	O4ⁱⁱ—Sm1—C18—O4	1.89 (11)
O1ⁱ—Sm1—O7—C27	89.35 (11)	O1W—Sm1—C18—O4	93.79 (16)
O4ⁱⁱ—Sm1—O7—C27	−98.15 (11)	O2—Sm1—C18—O4	79.32 (9)
O1W—Sm1—O7—C27	170.79 (11)	O8—Sm1—C18—O4	−85.80 (9)
O2—Sm1—O7—C27	−140.97 (10)	O7—Sm1—C18—O4	−72.50 (10)
O8—Sm1—O7—C27	2.16 (9)	O5—Sm1—C18—O4	179.92 (16)
O5—Sm1—O7—C27	17.23 (12)	O1—Sm1—C18—O4	130.01 (9)
O4—Sm1—O7—C27	−41.05 (11)	C27—Sm1—C18—O4	−78.68 (10)
O1—Sm1—O7—C27	129.50 (10)	C9—Sm1—C18—O4	103.82 (10)
C9—Sm1—O7—C27	173.03 (10)	C24—C19—C20—C21	0.0 (6)
C18—Sm1—O7—C27	−13.98 (12)	C19—C20—C21—C22	0.9 (6)
O1ⁱ—Sm1—O8—C27	−87.21 (10)	C20—C21—C22—C23	−1.5 (6)
O4ⁱⁱ—Sm1—O8—C27	69.81 (10)	C21—C22—C23—C24	1.1 (5)
O1W—Sm1—O8—C27	−15.98 (12)	C21—C22—C23—C25	−177.8 (3)
O2—Sm1—O8—C27	133.36 (11)	C20—C19—C24—C23	−0.4 (5)
O7—Sm1—O8—C27	−2.16 (9)	O9—C19—C24—C23	179.8 (3)
O5—Sm1—O8—C27	−169.92 (10)	C22—C23—C24—C19	−0.2 (5)
O4—Sm1—O8—C27	136.53 (10)	C25—C23—C24—C19	178.7 (3)
O1—Sm1—O8—C27	−127.82 (10)	C22—C23—C25—C26	168.4 (3)
C9—Sm1—O8—C27	−169.02 (11)	C24—C23—C25—C26	−10.5 (4)
C18—Sm1—O8—C27	163.84 (11)	C23—C25—C26—C27	−178.1 (2)
O3—C1—C2—C3	−178.3 (2)	Sm1—O7—C27—O8	−3.80 (17)
C6—C1—C2—C3	1.5 (3)	Sm1—O7—C27—C26	176.78 (15)
C1—C2—C3—C4	0.9 (4)	Sm1—O8—C27—O7	3.86 (17)
C2—C3—C4—C5	−1.5 (4)	Sm1—O8—C27—C26	−176.71 (14)
C3—C4—C5—C6	−0.4 (3)	C25—C26—C27—O7	0.8 (3)
C3—C4—C5—C7	174.3 (2)	C25—C26—C27—O8	−178.66 (19)
O3—C1—C6—C5	176.38 (18)	O1ⁱ—Sm1—C27—O7	−86.87 (10)
C2—C1—C6—C5	−3.5 (3)	O4ⁱⁱ—Sm1—C27—O7	76.12 (10)
C4—C5—C6—C1	2.9 (3)	O1W—Sm1—C27—O7	−9.11 (11)
C7—C5—C6—C1	−172.11 (18)	O2—Sm1—C27—O7	82.40 (16)
C4—C5—C7—C8	−7.3 (3)	O8—Sm1—C27—O7	−176.12 (17)
C6—C5—C7—C8	167.4 (2)	O5—Sm1—C27—O7	−166.09 (10)
C5—C7—C8—C9	−171.47 (18)	O4—Sm1—C27—O7	142.72 (10)
Sm1—O2—C9—O1	−11.77 (18)	O1—Sm1—C27—O7	−86.56 (14)
Sm1—O2—C9—C8	165.59 (15)	C18—Sm1—C27—O7	168.29 (10)
Sm1ⁱ—O1—C9—O2	165.90 (18)	O1ⁱ—Sm1—C27—O8	89.25 (10)
Sm1—O1—C9—O2	11.05 (17)	O4ⁱⁱ—Sm1—C27—O8	−107.76 (10)
Sm1ⁱ—O1—C9—C8	−11.5 (4)	O1W—Sm1—C27—O8	167.01 (10)
Sm1—O1—C9—C8	−166.37 (15)	O2—Sm1—C27—O8	−101.48 (16)
Sm1ⁱ—O1—C9—Sm1	154.8 (3)	O7—Sm1—C27—O8	176.12 (17)
C7—C8—C9—O2	−4.1 (3)	O5—Sm1—C27—O8	10.03 (10)
C7—C8—C9—O1	173.30 (18)	O4—Sm1—C27—O8	−41.16 (10)
C7—C8—C9—Sm1	75.2 (6)	O1—Sm1—C27—O8	89.55 (12)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5ⁱ	0.82 (2)	2.02 (2)	2.8183 (18)	163 (2)
O3—H3···O8ⁱⁱⁱ	0.91 (2)	1.76 (2)	2.6692 (19)	176 (3)
O6—H6···O7^iv	0.92 (2)	1.78 (2)	2.7005 (19)	174 (3)
O2W—H2WA···O9^v	0.84 (2)	2.15 (2)	2.947 (4)	158 (3)
O1W—H1WB···O2Wⁱⁱ	0.83 (2)	1.86 (2)	2.688 (2)	175 (2)
O2W—H2WB···O3^vi	0.81 (2)	1.98 (2)	2.790 (3)	173 (4)

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

Experimental details

Crystal data
Chemical formula	[Sm(C₉H₇O₃)₃(H₂O)]·H₂O
M_r	675.82
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.9411 (1), 13.0312 (2), 13.6564 (2)
α, β, γ (°)	97.356 (1), 97.120 (1), 103.739 (1)
V (Å³)	1343.87 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.25
Crystal size (mm)	0.52 × 0.24 × 0.15

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.53, 0.71
No. of measured, independent and observed [I > 2σ(I)] reflections	17958, 4722, 4590
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.014, 0.037, 1.04
No. of reflections	4722
No. of parameters	373
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.47

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5ⁱ	0.824 (15)	2.022 (16)	2.8183 (18)	163 (2)
O3—H3···O8ⁱⁱ	0.906 (17)	1.764 (17)	2.6692 (19)	176 (3)
O6—H6···O7ⁱⁱⁱ	0.923 (17)	1.781 (17)	2.7005 (19)	174 (3)
O2W—H2WA···O9^iv	0.844 (17)	2.15 (2)	2.947 (4)	158 (3)
O1W—H1WB···O2W^v	0.834 (16)	1.856 (16)	2.688 (2)	175 (2)
O2W—H2WB···O3^vi	0.814 (17)	1.980 (18)	2.790 (3)	173 (4)

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

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Marsh, R. E. (2009). Acta Cryst. B65, 782–783. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Niu, C. Y., Wu, B. L., Zheng, X. F., Zhang, H. Y., Hou, H. W., Niu, Y. Y. & Li, Z. J. (2008). Cryst. Growth Des. 8, 1566–1574. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). 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
Tang, Z.-W., Fu, J.-D., Jiang, L.-P. & Wen, Y.-H. (2009). Acta Cryst. E65, m979. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, X.-J. & Feng, Y.-L. (2010). Acta Cryst. E66, o1298. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xue, D. X., Lin, Y. Y., Cheng, X. N. & Cheng, X. M. (2007). Cryst. Growth Des. 7, 1332–1336. Web of Science CSD CrossRef CAS Google Scholar
Yan, J., Guo, Y. M., Li, H., Sun, X. P. & Wang, Z. (2008). J. Mol. Struct. 891, 298–304. Web of Science CSD CrossRef CAS Google Scholar
Ye, B.-H., Tong, M.-L. & Chen, X.-M. (2005). Coord. Chem. Rev. 249, 545–565. Web of Science CrossRef CAS Google Scholar

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