Triaqua­bis­{2-meth­oxy-6-[(phenyl­iminium­yl)meth­yl]phenolate-κO1}manganese(II) dinitrate

Ge, G.-D.; Shen, J.-B.; Zhao, G.-L.

doi:10.1107/S1600536811019593

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m813-m814

doi:10.1107/S1600536811019593

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Triaquabis{2-methoxy-6-[(phenyliminiumyl)methyl]phenolate-κO¹}manganese(II) dinitrate

Guo-Di Ge,^a Jin-Bei Shen ^a and Guo-Liang Zhao ^a,^b ^*

^aCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and ^bZhejiang Normal University Xingzhi College, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 25 March 2011; accepted 24 May 2011; online 28 May 2011)

The crystal structure of the title compound, [Mn(C₁₄H₁₃NO₂)₂(H₂O)₃](NO₃)₂, is comprised of two Schiff base 2-methoxy-6-(N-phenylcarboximidoyl)phenol (HL) ligands and three coordinated water molecules. The Mn^II ion lies on a twofold axis that bisects one water O atom. The coordination sphere of the five-coordinate Mn atom is completed by the two monodentate HL ligands and three coordinated water molecules binding through their O atoms, affording a distorted tetragonal–pyramidal geometry. In the phenolate ligands, the hydroxy H atom transfers to the imine N atom. This H atom is also involved in an intramolecular N—H⋯O hydrogen bond that imposes a nearly planar conformation on each ligand, with dihedral angles of 2.78 (3) and 2.43 (5)° between the aromatic rings of each ligand. In the crystal, molecules are linked by intermolecular O—H⋯O hydrogen bonds.

Related literature

For Schiff base ligands derived from o-vanillin and aniline and their rare earth complexes, see: Garnovskii et al. (1993 ); Shen et al. (2011 ); Zhao et al. (2006 ). For the synthesis of related Schiff bases, see: Burrows & Bailar (1966 ).

Experimental

Crystal data

[Mn(C₁₄H₁₃NO₂)₂(H₂O)₃](NO₃)₂
M_r = 687.52
Orthorhombic, P b c n
a = 17.4364 (3) Å
b = 10.4199 (2) Å
c = 16.9014 (3) Å
V = 3070.74 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 296 K
0.26 × 0.14 × 0.06 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.918, T_max = 0.969
11534 measured reflections
2705 independent reflections
1864 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.118
S = 1.07
2705 reflections
210 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O5ⁱ	0.85	2.18	3.032 (3)	180
O1W—H1WB⋯O4ⁱⁱ	0.85	1.96	2.809 (3)	180
O2W—H2WA⋯O3ⁱⁱ	0.85	1.96	2.800 (3)	169
N1—H1A⋯O1	0.86	1.92	2.611 (2)	137
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock global. DOI: 10.1107/S1600536811019593/rn2084sup1.cif

checkCIF report

Comment top

It has well been documented that Schiff bases are important in diverse fields of chemistry and biochemistry owing to their biological activities (Garnovskii et al., 1993). The complexes prepared by ligands derived from o -vanillin have attracted considerable attention for a number of years due to the intriguing biological activities of o-vanillin and the convenience of the synthesis of related Schiff bases (Burrows & Bailar, 1966). For these reasons, we have been engaged in the syntheses of new Schiff bases derived from o-vanillin and their transition and rare earth metal complexes (Shen et al. 2011; Zhao et al. 2006). Herein, we describe a new Mn^II complex.

The structure of complex (1) is shown in Fig. 1, which contains two 2-methoxy-6-(N-phenylcarboximidoyl)phenol (HL) ligands, three coordinated water molecules and two independent nitrate ions. The coordination sphere of the five-coordinate Mn atom is completed by the two monodentate HL ligands and three coordinated water molecules binding through their O atoms, affording a distorted tetragonal pyramid geometry. The coordination geometry around Mn^II is better described as a distorted square pyramid with the basal positions occupied by the four O atoms; O1, O1A, O1W and O1WA. The apical position is occupied by O2W. The Mn^II ion lies on a twofold axis that bisects O2W. The five Mn—O bond distances are listed in Table 1.The Mn—O (phenolic) bonds are 2.118 (4) Å, which are shorter than the similar reported complexes (Shen et al. 2011).

The hydrogen bonds lend stability to the structure. The packing plot of this compound is shown in Fig. 2. In the phenolate ligands, the proton of the phenolic hydroxy group transfers to the imine N atom. This proton is also involved in an intramolecular N—H···O hydrogen bond that imposes a nearly planar conformation on each ligand, with dihedral angles of 2.78 (3) and 2.43 (5)° between the aromatic rings of each ligand. In the crystal structure, molecules are linked by intermolecular O—H···O hydrogen bonds.

Related literature top

For Schiff base ligands derived from o-vanillin and aniline and their rare earth complexes, see: Garnovskii et al. (1993); Shen et al. (2011); Zhao et al. (2006). For the synthesis of related Schiff bases, see: Burrows & Bailar (1966).

Experimental top

Reagents and solvents used were of commercially available quality. The Schiff base ligand 2-methoxy-6-(N-phenylcarboximidoyl)phenol was synthesized from condensation of o-vanillin and aniline. 1 mmol HLligand was dissolved in ethanol(20 ml), then 0.5 mmol Manganese nitrate solution (in ethanol). The mixture solution was stirred for 4 h at room temperature. The resulting solid was filtered out and the solution evaporated yielding red crystals of compound (1) after several 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. (The atoms labelled with the suffix A are related by the symmetry operation -x + 1,-y,-z + 1)
	Fig. 2. The packing plot of the title compound, showing H-bond interactions (dashed lines).

Triaquabis{2-methoxy-6-[(phenyliminiumyl)methyl]phenolate- κO¹}manganese(II) dinitrate top

Crystal data top

[Mn(C₁₄H₁₃NO₂)₂(H₂O)₃](NO₃)₂	F(000) = 1428
M_r = 687.52	D_x = 1.487 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2780 reflections
a = 17.4364 (3) Å	θ = 2.3–25.0°
b = 10.4199 (2) Å	µ = 0.50 mm⁻¹
c = 16.9014 (3) Å	T = 296 K
V = 3070.74 (10) Å³	Block, red
Z = 4	0.26 × 0.14 × 0.06 mm

Data collection top

Bruker APEXII area-detector diffractometer	2705 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→20
T_min = 0.918, T_max = 0.969	k = −12→12
11534 measured reflections	l = −19→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0599P)²] where P = (F_o² + 2F_c²)/3
2705 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.22 e Å⁻³
4 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Mn(C₁₄H₁₃NO₂)₂(H₂O)₃](NO₃)₂	V = 3070.74 (10) Å³
M_r = 687.52	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 17.4364 (3) Å	µ = 0.50 mm⁻¹
b = 10.4199 (2) Å	T = 296 K
c = 16.9014 (3) Å	0.26 × 0.14 × 0.06 mm

Data collection top

Bruker APEXII area-detector diffractometer	2705 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1864 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.969	R_int = 0.035
11534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	4 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.07	Δρ_max = 0.22 e Å⁻³
2705 reflections	Δρ_min = −0.33 e Å⁻³
210 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
Mn1	0.5000	0.33828 (5)	0.2500	0.0421 (2)
O1	0.38704 (9)	0.30891 (16)	0.29244 (10)	0.0460 (5)
O1W	0.46876 (11)	0.3817 (2)	0.12448 (11)	0.0662 (6)
H1WA	0.4674	0.3323	0.0845	0.099*
H1WB	0.4722	0.4555	0.1034	0.099*
O2	0.43669 (10)	0.13545 (17)	0.19361 (11)	0.0597 (6)
O2W	0.5000	0.5493 (2)	0.2500	0.0604 (8)
H2WA	0.5076	0.6037	0.2134	0.091*
N1	0.27417 (11)	0.4077 (2)	0.37372 (11)	0.0414 (5)
H1A	0.3225	0.4015	0.3645	0.050*
C1	0.15746 (18)	0.6407 (3)	0.48555 (17)	0.0601 (8)
H1	0.1066	0.6663	0.4902	0.072*
C2	0.2127 (2)	0.7023 (3)	0.52808 (17)	0.0611 (8)
H2	0.1996	0.7697	0.5615	0.073*
C3	0.28780 (19)	0.6644 (3)	0.52134 (17)	0.0606 (8)
H3	0.3255	0.7060	0.5507	0.073*
C4	0.30785 (16)	0.5658 (3)	0.47178 (15)	0.0518 (7)
H4	0.3588	0.5402	0.4678	0.062*
C5	0.25210 (14)	0.5048 (2)	0.42797 (14)	0.0404 (6)
C6	0.17617 (15)	0.5410 (3)	0.43588 (16)	0.0532 (7)
H6	0.1381	0.4982	0.4078	0.064*
C7	0.23079 (14)	0.3276 (2)	0.33641 (15)	0.0418 (6)
H7	0.1785	0.3294	0.3470	0.050*
C8	0.25749 (14)	0.2381 (2)	0.28081 (14)	0.0395 (6)
C9	0.33671 (14)	0.2317 (2)	0.26127 (14)	0.0394 (6)
C10	0.35947 (15)	0.1353 (2)	0.20736 (15)	0.0436 (6)
C11	0.30689 (17)	0.0538 (2)	0.17469 (16)	0.0536 (7)
H11	0.3233	−0.0087	0.1393	0.064*
C12	0.22898 (16)	0.0622 (3)	0.19330 (16)	0.0533 (7)
H12	0.1941	0.0060	0.1703	0.064*
C13	0.20462 (16)	0.1525 (3)	0.24499 (15)	0.0479 (7)
H13	0.1527	0.1585	0.2572	0.057*
C14	0.46842 (18)	0.0327 (3)	0.1474 (2)	0.0848 (11)
H14A	0.5233	0.0405	0.1460	0.102*
H14B	0.4485	0.0369	0.0945	0.102*
H14C	0.4547	−0.0481	0.1708	0.102*
O5	0.03646 (13)	0.2937 (2)	0.48143 (13)	0.0812 (7)
O3	0.04351 (13)	0.2360 (2)	0.36037 (13)	0.0807 (7)
O4	−0.02028 (16)	0.1259 (2)	0.44494 (15)	0.0969 (8)
N3	0.02000 (14)	0.2189 (3)	0.42868 (17)	0.0580 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0316 (4)	0.0502 (4)	0.0447 (4)	0.000	0.0042 (2)	0.000
O1	0.0337 (10)	0.0565 (11)	0.0479 (11)	−0.0064 (9)	0.0031 (9)	−0.0088 (9)
O1W	0.0830 (14)	0.0674 (13)	0.0484 (11)	0.0038 (12)	−0.0137 (11)	−0.0008 (11)
O2	0.0445 (12)	0.0622 (12)	0.0725 (13)	0.0052 (9)	0.0152 (10)	−0.0130 (11)
O2W	0.080 (2)	0.0509 (17)	0.0506 (16)	0.000	0.0063 (14)	0.000
N1	0.0292 (11)	0.0542 (13)	0.0408 (12)	0.0027 (10)	0.0044 (10)	0.0003 (11)
C1	0.057 (2)	0.0640 (19)	0.0593 (19)	0.0149 (16)	0.0125 (16)	−0.0020 (17)
C2	0.086 (3)	0.0493 (17)	0.0481 (18)	0.0032 (17)	0.0109 (17)	−0.0025 (15)
C3	0.072 (2)	0.0544 (17)	0.0554 (19)	−0.0096 (16)	−0.0029 (16)	−0.0059 (16)
C4	0.0437 (17)	0.0572 (17)	0.0545 (17)	−0.0043 (14)	−0.0016 (14)	−0.0017 (15)
C5	0.0382 (15)	0.0468 (14)	0.0363 (14)	0.0017 (12)	0.0056 (12)	0.0064 (13)
C6	0.0425 (17)	0.0627 (18)	0.0545 (16)	0.0024 (14)	−0.0021 (14)	−0.0039 (16)
C7	0.0298 (14)	0.0500 (14)	0.0458 (14)	−0.0028 (12)	0.0012 (11)	0.0035 (11)
C8	0.0338 (15)	0.0449 (14)	0.0397 (13)	−0.0032 (11)	−0.0004 (11)	0.0058 (11)
C9	0.0375 (15)	0.0440 (15)	0.0367 (14)	−0.0011 (13)	0.0002 (12)	0.0054 (12)
C10	0.0432 (17)	0.0434 (15)	0.0441 (16)	0.0031 (13)	0.0052 (13)	0.0026 (13)
C11	0.070 (2)	0.0427 (16)	0.0477 (17)	−0.0044 (15)	0.0059 (15)	−0.0051 (14)
C12	0.0534 (19)	0.0541 (17)	0.0525 (17)	−0.0150 (14)	−0.0026 (15)	0.0015 (16)
C13	0.0366 (16)	0.0565 (17)	0.0505 (17)	−0.0084 (13)	0.0004 (12)	0.0025 (15)
C14	0.072 (2)	0.082 (2)	0.101 (3)	0.014 (2)	0.027 (2)	−0.027 (2)
O5	0.0847 (17)	0.0844 (16)	0.0745 (15)	0.0036 (13)	−0.0044 (13)	−0.0299 (14)
O3	0.0851 (17)	0.0974 (18)	0.0595 (13)	−0.0022 (14)	0.0156 (13)	−0.0015 (14)
O4	0.128 (2)	0.0688 (15)	0.0942 (19)	−0.0224 (15)	0.0255 (17)	−0.0070 (15)
N3	0.0543 (16)	0.0531 (16)	0.0666 (17)	0.0138 (13)	0.0033 (14)	−0.0050 (17)

Geometric parameters (Å, º) top

Mn1—O1	2.1184 (16)	C3—H3	0.9300
Mn1—O1ⁱ	2.1184 (16)	C4—C5	1.377 (3)
Mn1—O2W	2.199 (3)	C4—H4	0.9300
Mn1—O1W	2.2365 (18)	C5—C6	1.383 (3)
Mn1—O1Wⁱ	2.2366 (18)	C6—H6	0.9300
Mn1—O2	2.5678 (19)	C7—C8	1.403 (3)
Mn1—O2ⁱ	2.5678 (19)	C7—H7	0.9300
O1—C9	1.302 (3)	C8—C13	1.419 (3)
O1W—H1WA	0.8500	C8—C9	1.422 (3)
O1W—H1WB	0.8501	C9—C10	1.413 (3)
O2—C10	1.366 (3)	C10—C11	1.366 (3)
O2—C14	1.436 (3)	C11—C12	1.397 (4)
O2W—H2WA	0.8500	C11—H11	0.9300
N1—C7	1.291 (3)	C12—C13	1.352 (4)
N1—C5	1.419 (3)	C12—H12	0.9300
N1—H1A	0.8600	C13—H13	0.9300
C1—C2	1.363 (4)	C14—H14A	0.9600
C1—C6	1.375 (3)	C14—H14B	0.9600
C1—H1	0.9300	C14—H14C	0.9600
C2—C3	1.372 (4)	O5—N3	1.218 (3)
C2—H2	0.9300	O3—N3	1.238 (3)
C3—C4	1.371 (4)	O4—N3	1.228 (3)

O1—Mn1—O1ⁱ	163.38 (9)	C2—C3—H3	119.7
O1—Mn1—O2W	98.31 (5)	C3—C4—C5	119.6 (3)
O1ⁱ—Mn1—O2W	98.31 (5)	C3—C4—H4	120.2
O1—Mn1—O1W	97.12 (7)	C5—C4—H4	120.2
O1ⁱ—Mn1—O1W	86.24 (7)	C4—C5—C6	119.9 (3)
O2W—Mn1—O1W	78.33 (5)	C4—C5—N1	119.0 (2)
O1—Mn1—O1Wⁱ	86.24 (7)	C6—C5—N1	121.1 (2)
O1ⁱ—Mn1—O1Wⁱ	97.12 (7)	C1—C6—C5	119.5 (3)
O2W—Mn1—O1Wⁱ	78.33 (5)	C1—C6—H6	120.3
O1W—Mn1—O1Wⁱ	156.67 (11)	C5—C6—H6	120.3
O1—Mn1—O2	66.86 (6)	N1—C7—C8	124.2 (2)
O1ⁱ—Mn1—O2	98.93 (6)	N1—C7—H7	117.9
O2W—Mn1—O2	145.39 (4)	C8—C7—H7	117.9
O1W—Mn1—O2	73.12 (7)	C7—C8—C13	119.2 (2)
O1Wⁱ—Mn1—O2	128.55 (7)	C7—C8—C9	120.6 (2)
O1—Mn1—O2ⁱ	98.93 (6)	C13—C8—C9	120.2 (2)
O1ⁱ—Mn1—O2ⁱ	66.86 (6)	O1—C9—C10	120.7 (2)
O2W—Mn1—O2ⁱ	145.39 (4)	O1—C9—C8	122.1 (2)
O1W—Mn1—O2ⁱ	128.55 (7)	C10—C9—C8	117.1 (2)
O1Wⁱ—Mn1—O2ⁱ	73.12 (7)	C11—C10—O2	126.4 (2)
O2—Mn1—O2ⁱ	69.21 (8)	C11—C10—C9	120.9 (2)
C9—O1—Mn1	125.39 (15)	O2—C10—C9	112.7 (2)
Mn1—O1W—H1WA	129.7	C10—C11—C12	121.5 (2)
Mn1—O1W—H1WB	124.3	C10—C11—H11	119.3
H1WA—O1W—H1WB	102.5	C12—C11—H11	119.3
C10—O2—C14	118.1 (2)	C13—C12—C11	119.6 (3)
C10—O2—Mn1	111.19 (15)	C13—C12—H12	120.2
C14—O2—Mn1	130.53 (16)	C11—C12—H12	120.2
Mn1—O2W—H2WA	131.8	C12—C13—C8	120.6 (3)
C7—N1—C5	128.2 (2)	C12—C13—H13	119.7
C7—N1—H1A	116.0	C8—C13—H13	119.7
C5—N1—H1A	115.9	O2—C14—H14A	109.5
C2—C1—C6	120.7 (3)	O2—C14—H14B	109.5
C2—C1—H1	119.7	H14A—C14—H14B	109.5
C6—C1—H1	119.7	O2—C14—H14C	109.5
C1—C2—C3	119.7 (3)	H14A—C14—H14C	109.5
C1—C2—H2	120.2	H14B—C14—H14C	109.5
C3—C2—H2	120.2	O5—N3—O4	118.4 (3)
C4—C3—C2	120.6 (3)	O5—N3—O3	120.8 (3)
C4—C3—H3	119.7	O4—N3—O3	120.8 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5ⁱⁱ	0.85	2.18	3.032 (3)	180
O1W—H1WB···O4ⁱⁱⁱ	0.85	1.96	2.809 (3)	180
O2W—H2WA···O3ⁱⁱⁱ	0.85	1.96	2.800 (3)	169
N1—H1A···O1	0.86	1.92	2.611 (2)	137

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

Experimental details

Crystal data
Chemical formula	[Mn(C₁₄H₁₃NO₂)₂(H₂O)₃](NO₃)₂
M_r	687.52
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	296
a, b, c (Å)	17.4364 (3), 10.4199 (2), 16.9014 (3)
V (Å³)	3070.74 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.26 × 0.14 × 0.06

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.918, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	11534, 2705, 1864
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.118, 1.07
No. of reflections	2705
No. of parameters	210
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.33

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), 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
O1W—H1WA···O5ⁱ	0.85	2.18	3.032 (3)	180
O1W—H1WB···O4ⁱⁱ	0.85	1.96	2.809 (3)	180
O2W—H2WA···O3ⁱⁱ	0.85	1.96	2.800 (3)	169
N1—H1A···O1	0.86	1.92	2.611 (2)	137

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

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burrows, R. C. & Bailar, J. C. (1966). J. Am. Chem. Soc. 88, 4150–4152. CrossRef CAS Web of Science Google Scholar
Garnovskii, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. CrossRef CAS Web of Science 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
Shen, J.-B., Ge, G.-D. & Zhao, G.-L. (2011). Acta Cryst. E67, m463. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, G.-L., Feng, Y.-L. & Wen, Y.-H. (2006). J. Rare Earth, 24, 268–275. CrossRef Google Scholar

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