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Acta Cryst. (2009). E65, m151-m152    [ doi:10.1107/S1600536808043948 ]

Bis(6-methoxy-2-{[tris(hydroxymethyl)methyl]iminomethyl}phenolato)copper(II) dihydrate

X. Zhang, P. Wei, J. Dou, B. Li and B. Hu

Abstract top

In the title compound, [Cu(C12H16NO5)2]·2H2O, the CuII ion adopts a trans-CuN2O4 octahedral geometry arising from two N,O,O'-tridentate 6-methoxy-2-{[tris(hydroxymethyl)methyl]iminomethyl}phenolate ligands. The Jahn-Teller distortion of the copper centre is unusally small. In the crystal structure, O-H...O hydrogen bonds, some of which are bifurcated, link the component species.

Comment top

Transition metal-Schiff based complexes have been intensely focused on owing to their excellent physical and chemical properties including magnetic, optics and catalysis (Ward, 2007). Herein, we report the crystal structure of the title compound, (I), based on a Schiff base ligand, L, (E)-2-(2-hydroxy-3-methoxybenzylideneamino)-2-(hydroxymethyl)propane-1,3-diol, (Fig. 1).

The CuII ion in (I) is surrounded by two L-1 ligands and hexa-coordinated by four oxygen atoms and two nitrogen atoms, with a slightly distorted octahedral coordination sphere (Table 1). The metal–ligand bond distances are similar to those in a related structure (Wang et al., 2007). In the crystal, a network of O—H···O hydrogen bonds (Table 2) help to establish the packing.

Related literature top

For the ligand synthesis, see: Wang et al. (2007). For background on Schiff base complexes, see: Ward (2007).

Experimental top

The ligand (HL) was synthesized according to the literature method (Wang et al., 2007). HL1 (0.050 g, 0.2 mmol) and Cu(OAc)2.4H2O (0.0498 g, 0.2 mmol) were refluxed in a mixed solvent solution (CH3OH:H2O = 4:1 v/v) until all solid was dissolved. The solution was cooled to room temperature and filtrated and blue blocks of (I) slowly grew by allowing slow evaporation of the solution. Anal. Calc. for C24H36CuN2O12: C 47.36, H 5.92, N 4.60%; Found: C 47.25, H 5.78, N 4.54%.

Refinement top

The non-water H atoms were geometrically placed (C—H = 0.93–0.97 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C). The water H atoms were located in a difference map and reifned with restraints of O—H = 0.82 (2)Å and H···H = 1.37 (2)Å and with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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
[Figure 1] Fig. 1. A view of (I) with Displacement ellipsoids drawn at the 30% probability level.
Bis(6-methoxy-2-{[tris(hydroxymethyl)methyl]iminomethyl}phenolato)copper(II) dihydrate top
Crystal data top
[Cu(C12H16NO5)2]·2H2OF(000) = 1276
Mr = 608.09Dx = 1.497 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4912 reflections
a = 11.9421 (9) Åθ = 2.1–25.5°
b = 11.0238 (9) ŵ = 0.88 mm−1
c = 20.6706 (17) ÅT = 293 K
β = 97.462 (1)°Block, blue
V = 2698.2 (4) Å30.12 × 0.10 × 0.08 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		4912 independent reflections
Radiation source: fine-focus sealed tube4397 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
ω scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −14→11
Tmin = 0.902, Tmax = 0.933k = −13→13
13183 measured reflectionsl = −25→21
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.076P)2 + 1.4852P]
where P = (Fo2 + 2Fc2)/3
4912 reflections(Δ/σ)max = 0.010
352 parametersΔρmax = 0.47 e Å−3
8 restraintsΔρmin = −0.48 e Å−3
Crystal data top
[Cu(C12H16NO5)2]·2H2OV = 2698.2 (4) Å3
Mr = 608.09Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.9421 (9) ŵ = 0.88 mm−1
b = 11.0238 (9) ÅT = 293 K
c = 20.6706 (17) Å0.12 × 0.10 × 0.08 mm
β = 97.462 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		4912 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		4397 reflections with I > 2σ(I)
Tmin = 0.902, Tmax = 0.933Rint = 0.061
13183 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.117Δρmax = 0.47 e Å−3
S = 1.01Δρmin = −0.48 e Å−3
4912 reflectionsAbsolute structure: ?
352 parametersFlack parameter: ?
8 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Cu10.76750 (2)0.15964 (2)0.742179 (13)0.02060 (12)
C10.8354 (4)0.4629 (4)0.52078 (18)0.0604 (10)
H1A0.90900.49800.53160.091*
H1B0.78470.52260.49970.091*
H1C0.84000.39530.49190.091*
C20.6893 (2)0.3686 (2)0.57268 (13)0.0304 (6)
C30.6096 (3)0.3782 (3)0.51893 (14)0.0448 (8)
H30.62570.42350.48330.054*
C40.5048 (3)0.3213 (3)0.51666 (16)0.0490 (9)
H40.45040.33030.48050.074*
C50.4835 (3)0.2521 (3)0.56846 (14)0.0386 (7)
H50.41410.21320.56680.058*
C60.5636 (2)0.2380 (2)0.62432 (12)0.0250 (5)
C70.6687 (2)0.3017 (2)0.62939 (11)0.0212 (5)
C80.5359 (2)0.1518 (2)0.67278 (13)0.0245 (5)
H80.46200.12300.66790.029*
C90.5630 (2)0.0167 (2)0.76438 (12)0.0241 (5)
C100.4561 (2)−0.0514 (2)0.73731 (14)0.0328 (6)
H10A0.4384−0.11110.76890.039*
H10B0.39350.00520.73010.039*
C110.5411 (2)0.0769 (3)0.82836 (14)0.0348 (6)
H11A0.52170.01570.85870.042*
H11B0.60880.11840.84800.042*
C120.6611 (2)−0.0728 (2)0.77953 (13)0.0290 (5)
H12A0.6453−0.12870.81350.035*
H12B0.6706−0.11950.74080.035*
C130.6631 (3)0.4397 (3)0.97678 (15)0.0459 (8)
H13A0.58410.45850.96840.069*
H13B0.70580.51360.98270.069*
H13C0.67730.39121.01560.069*
C140.8076 (2)0.3405 (2)0.92680 (12)0.0286 (6)
C150.8870 (3)0.3615 (3)0.97939 (13)0.0369 (6)
H150.86640.40061.01590.044*
C160.9992 (3)0.3245 (3)0.97888 (13)0.0362 (6)
H161.05290.33811.01490.043*
C171.0282 (2)0.2683 (2)0.92462 (12)0.0290 (5)
H171.10270.24460.92400.035*
C180.9483 (2)0.2451 (2)0.86945 (11)0.0211 (5)
C190.8334 (2)0.2797 (2)0.86871 (11)0.0209 (5)
C200.9936 (2)0.1931 (2)0.81378 (11)0.0207 (5)
H201.07150.18240.81800.025*
C210.9988 (2)0.1161 (2)0.70679 (11)0.0205 (5)
C221.1144 (2)0.0571 (2)0.72962 (12)0.0261 (5)
H22A1.14340.01900.69290.031*
H22B1.16790.11860.74730.031*
C231.0162 (2)0.2241 (2)0.66108 (11)0.0254 (5)
H23A1.06290.19800.62870.031*
H23B0.94360.24870.63830.031*
C240.9245 (2)0.0216 (2)0.66761 (12)0.0241 (5)
H24A0.95090.00870.62570.029*
H24B0.9288−0.05490.69090.029*
N10.60220 (16)0.11103 (17)0.72146 (10)0.0209 (4)
N20.93778 (16)0.16042 (16)0.75959 (9)0.0176 (4)
O10.79480 (18)0.4224 (2)0.57864 (10)0.0417 (5)
O20.74271 (14)0.30303 (15)0.68132 (8)0.0215 (3)
O30.76136 (14)−0.00642 (16)0.80055 (9)0.0287 (4)
H3A0.8136−0.05410.80320.043*
O40.46929 (17)−0.11041 (18)0.67767 (11)0.0403 (5)
H4A0.4108−0.14620.66400.060*
O50.4506 (2)0.16184 (19)0.81536 (13)0.0504 (6)
H5A0.43880.19420.84960.076*
O60.69604 (17)0.3742 (2)0.92296 (9)0.0424 (5)
O70.75320 (14)0.26443 (15)0.82097 (8)0.0237 (4)
O80.81044 (14)0.06366 (16)0.65805 (8)0.0279 (4)
H8A0.76760.01080.64330.042*
O91.10148 (16)−0.03065 (18)0.77788 (10)0.0378 (5)
H91.1627−0.06220.79010.057*
O101.06809 (16)0.32536 (16)0.69565 (9)0.0316 (4)
H101.02800.34890.72250.047*
O1W0.6645 (2)0.8968 (2)0.60223 (11)0.0496 (6)
H1W0.68720.82340.60270.074*
H2W0.60380.89850.61970.074*
O2W0.2699 (2)0.1555 (2)0.87731 (13)0.0553 (6)
H3W0.24130.08890.88850.083*
H4W0.32530.13870.85650.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02012 (18)0.01953 (18)0.02172 (18)−0.00072 (10)0.00112 (12)−0.00073 (10)
C10.086 (3)0.052 (2)0.051 (2)−0.0176 (19)0.0366 (19)0.0000 (16)
C20.0429 (15)0.0226 (12)0.0255 (13)−0.0034 (11)0.0034 (11)0.0012 (10)
C30.069 (2)0.0355 (16)0.0269 (14)−0.0041 (15)−0.0042 (14)0.0095 (12)
C40.062 (2)0.0405 (17)0.0370 (17)−0.0055 (15)−0.0241 (15)0.0080 (13)
C50.0390 (15)0.0282 (14)0.0432 (16)−0.0034 (12)−0.0149 (13)0.0016 (12)
C60.0266 (12)0.0197 (12)0.0268 (12)0.0017 (10)−0.0039 (10)−0.0009 (9)
C70.0263 (12)0.0148 (10)0.0220 (11)−0.0004 (9)0.0015 (9)−0.0013 (9)
C80.0208 (12)0.0193 (12)0.0322 (13)−0.0017 (9)−0.0008 (10)−0.0027 (9)
C90.0240 (12)0.0182 (11)0.0307 (12)−0.0052 (10)0.0059 (9)0.0033 (10)
C100.0236 (13)0.0249 (13)0.0496 (16)−0.0065 (10)0.0040 (11)0.0050 (12)
C110.0392 (15)0.0314 (14)0.0372 (15)−0.0034 (12)0.0180 (12)0.0028 (12)
C120.0283 (13)0.0195 (12)0.0387 (14)−0.0024 (10)0.0024 (11)0.0053 (10)
C130.0513 (18)0.0533 (19)0.0356 (15)0.0175 (15)0.0151 (13)−0.0120 (14)
C140.0338 (14)0.0300 (14)0.0223 (12)0.0064 (11)0.0047 (10)−0.0028 (10)
C150.0461 (17)0.0422 (16)0.0221 (13)0.0031 (13)0.0032 (12)−0.0104 (11)
C160.0391 (16)0.0463 (17)0.0207 (13)−0.0032 (13)−0.0056 (11)−0.0057 (11)
C170.0278 (13)0.0338 (14)0.0240 (12)0.0004 (11)−0.0019 (10)0.0005 (10)
C180.0243 (12)0.0198 (11)0.0193 (11)−0.0007 (9)0.0028 (9)0.0002 (9)
C190.0280 (12)0.0176 (11)0.0168 (10)−0.0012 (9)0.0016 (9)0.0009 (9)
C200.0192 (11)0.0184 (11)0.0237 (11)−0.0006 (9)0.0002 (9)0.0008 (9)
C210.0219 (11)0.0188 (11)0.0213 (11)−0.0001 (9)0.0044 (9)−0.0028 (9)
C220.0234 (12)0.0234 (12)0.0324 (13)0.0041 (10)0.0065 (10)−0.0009 (10)
C230.0303 (13)0.0243 (12)0.0230 (11)−0.0016 (10)0.0082 (10)0.0010 (9)
C240.0275 (12)0.0187 (11)0.0257 (12)0.0003 (10)0.0022 (9)−0.0062 (9)
N10.0182 (9)0.0171 (9)0.0274 (10)−0.0011 (8)0.0031 (8)−0.0003 (8)
N20.0189 (9)0.0155 (9)0.0189 (9)0.0008 (7)0.0040 (7)0.0006 (7)
O10.0490 (12)0.0433 (12)0.0344 (10)−0.0155 (10)0.0118 (9)0.0073 (9)
O20.0230 (8)0.0178 (8)0.0226 (8)−0.0040 (7)−0.0009 (6)0.0020 (6)
O30.0240 (9)0.0226 (9)0.0384 (10)0.0017 (7)−0.0004 (7)0.0041 (7)
O40.0328 (10)0.0305 (10)0.0542 (13)−0.0085 (8)−0.0070 (9)−0.0069 (9)
O50.0451 (13)0.0364 (12)0.0763 (17)0.0023 (9)0.0325 (12)−0.0080 (11)
O60.0365 (11)0.0621 (14)0.0288 (10)0.0173 (10)0.0040 (8)−0.0155 (9)
O70.0216 (8)0.0273 (9)0.0217 (8)0.0019 (7)0.0005 (7)−0.0058 (7)
O80.0248 (9)0.0262 (9)0.0313 (9)−0.0020 (7)−0.0019 (7)−0.0107 (7)
O90.0278 (10)0.0307 (10)0.0543 (12)0.0112 (8)0.0035 (9)0.0136 (9)
O100.0318 (10)0.0247 (9)0.0398 (11)−0.0078 (7)0.0103 (8)−0.0018 (8)
O1W0.0575 (14)0.0423 (13)0.0482 (13)−0.0186 (11)0.0043 (10)−0.0024 (10)
O2W0.0421 (13)0.0466 (14)0.0814 (18)0.0021 (10)0.0241 (12)−0.0010 (12)
Geometric parameters (Å, º) top
Cu1—N12.0367 (19)C13—H13B0.9600
Cu1—N22.0185 (19)C13—H13C0.9600
Cu1—O22.0180 (16)C14—C151.366 (4)
Cu1—O32.1989 (18)C14—O61.376 (3)
Cu1—O72.0220 (16)C14—C191.443 (3)
Cu1—O82.1537 (17)C15—C161.401 (4)
C1—O11.419 (4)C15—H150.9300
C1—H1A0.9600C16—C171.365 (4)
C1—H1B0.9600C16—H160.9300
C1—H1C0.9600C17—C181.412 (3)
C2—C31.370 (4)C17—H170.9300
C2—O11.383 (3)C18—C191.422 (3)
C2—C71.433 (4)C18—C201.452 (3)
C3—C41.396 (5)C19—O71.294 (3)
C3—H30.9300C20—N21.279 (3)
C4—C51.365 (5)C20—H200.9300
C4—H40.9300C21—N21.472 (3)
C5—C61.409 (4)C21—C241.530 (3)
C5—H50.9300C21—C221.544 (3)
C6—C71.430 (3)C21—C231.551 (3)
C6—C81.450 (4)C22—O91.412 (3)
C7—O21.299 (3)C22—H22A0.9700
C8—N11.278 (3)C22—H22B0.9700
C8—H80.9300C23—O101.423 (3)
C9—N11.481 (3)C23—H23A0.9700
C9—C101.524 (3)C23—H23B0.9700
C9—C121.533 (4)C24—O81.428 (3)
C9—C111.532 (4)C24—H24A0.9700
C10—O41.421 (4)C24—H24B0.9700
C10—H10A0.9700O3—H3A0.8115
C10—H10B0.9700O4—H4A0.8200
C11—O51.428 (4)O5—H5A0.8200
C11—H11A0.9700O8—H8A0.8085
C11—H11B0.9700O9—H90.8200
C12—O31.422 (3)O10—H100.8200
C12—H12A0.9700O1W—H1W0.8520
C12—H12B0.9700O1W—H2W0.8511
C13—O61.424 (3)O2W—H3W0.8541
C13—H13A0.9600O2W—H4W0.8538
O2—Cu1—N299.83 (7)H13A—C13—H13C109.5
O2—Cu1—O791.93 (7)H13B—C13—H13C109.5
N2—Cu1—O792.43 (7)C15—C14—O6124.6 (2)
O2—Cu1—N190.88 (7)C15—C14—C19122.7 (2)
N2—Cu1—N1164.82 (7)O6—C14—C19112.8 (2)
O7—Cu1—N197.97 (7)C14—C15—C16120.7 (2)
O2—Cu1—O884.98 (7)C14—C15—H15119.7
N2—Cu1—O878.82 (7)C16—C15—H15119.7
O7—Cu1—O8170.05 (7)C17—C16—C15118.9 (2)
N1—Cu1—O891.54 (7)C17—C16—H16120.6
O2—Cu1—O3168.97 (6)C15—C16—H16120.6
N2—Cu1—O390.59 (7)C16—C17—C18121.9 (2)
O7—Cu1—O391.22 (7)C16—C17—H17119.0
N1—Cu1—O378.22 (7)C18—C17—H17119.0
O8—Cu1—O393.58 (7)C17—C18—C19120.7 (2)
O1—C1—H1A109.5C17—C18—C20115.4 (2)
O1—C1—H1B109.5C19—C18—C20123.8 (2)
H1A—C1—H1B109.5O7—C19—C18126.2 (2)
O1—C1—H1C109.5O7—C19—C14118.6 (2)
H1A—C1—H1C109.5C18—C19—C14115.2 (2)
H1B—C1—H1C109.5N2—C20—C18126.8 (2)
C3—C2—O1124.6 (3)N2—C20—H20116.6
C3—C2—C7121.9 (3)C18—C20—H20116.6
O1—C2—C7113.5 (2)N2—C21—C24108.05 (19)
C2—C3—C4121.2 (3)N2—C21—C22114.98 (19)
C2—C3—H3119.4C24—C21—C22108.01 (19)
C4—C3—H3119.4N2—C21—C23108.37 (18)
C5—C4—C3118.9 (3)C24—C21—C23108.33 (19)
C5—C4—H4120.6C22—C21—C23108.92 (19)
C3—C4—H4120.6O9—C22—C21109.19 (19)
C4—C5—C6121.9 (3)O9—C22—H22A109.8
C4—C5—H5119.0C21—C22—H22A109.8
C6—C5—H5119.1O9—C22—H22B109.8
C5—C6—C7120.1 (2)C21—C22—H22B109.8
C5—C6—C8116.5 (2)H22A—C22—H22B108.3
C7—C6—C8123.3 (2)O10—C23—C21112.36 (19)
O2—C7—C6124.2 (2)O10—C23—H23A109.1
O2—C7—C2120.0 (2)C21—C23—H23A109.1
C6—C7—C2115.8 (2)O10—C23—H23B109.1
N1—C8—C6126.9 (2)C21—C23—H23B109.1
N1—C8—H8116.6H23A—C23—H23B107.9
C6—C8—H8116.6O8—C24—C21109.23 (18)
N1—C9—C10116.2 (2)O8—C24—H24A109.8
N1—C9—C12106.37 (19)C21—C24—H24A109.8
C10—C9—C12109.9 (2)O8—C24—H24B109.8
N1—C9—C11108.37 (19)C21—C24—H24B109.8
C10—C9—C11107.6 (2)H24A—C24—H24B108.3
C12—C9—C11108.3 (2)C8—N1—C9120.4 (2)
O4—C10—C9111.2 (2)C8—N1—Cu1123.88 (17)
O4—C10—H10A109.4C9—N1—Cu1115.57 (15)
C9—C10—H10A109.4C20—N2—C21119.4 (2)
O4—C10—H10B109.4C20—N2—Cu1123.80 (16)
C9—C10—H10B109.4C21—N2—Cu1116.77 (14)
H10A—C10—H10B108.0C2—O1—C1117.8 (2)
O5—C11—C9109.3 (2)C7—O2—Cu1122.38 (14)
O5—C11—H11A109.8C12—O3—Cu1110.35 (14)
C9—C11—H11A109.8C12—O3—H3A107.2
O5—C11—H11B109.8Cu1—O3—H3A119.7
C9—C11—H11B109.8C10—O4—H4A109.5
H11A—C11—H11B108.3C11—O5—H5A109.5
O3—C12—C9108.8 (2)C14—O6—C13117.1 (2)
O3—C12—H12A109.9C19—O7—Cu1123.85 (15)
C9—C12—H12A109.9C24—O8—Cu1111.75 (13)
O3—C12—H12B109.9C24—O8—H8A111.3
C9—C12—H12B109.9Cu1—O8—H8A117.0
H12A—C12—H12B108.3C22—O9—H9109.5
O6—C13—H13A109.5C23—O10—H10109.5
O6—C13—H13B109.5H1W—O1W—H2W107.6
H13A—C13—H13B109.5H3W—O2W—H4W108.2
O6—C13—H13C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O10i0.811.942.748 (3)176
O4—H4A···O6ii0.822.082.681 (3)130
O4—H4A···O7ii0.822.252.997 (3)152
O5—H5A···O2W0.822.212.649 (4)114
O8—H8A···O1Wiii0.811.882.689 (3)175
O9—H9···O2i0.821.912.670 (3)153
O10—H10···O9iv0.822.042.685 (3)135
O1W—H1W···O2Wv0.851.952.790 (3)168
O1W—H2W···O4vi0.852.132.969 (3)170
O2W—H3W···O1ii0.852.022.866 (3)169
O2W—H4W···O50.851.832.649 (4)159
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y−1, z; (iv) −x+2, y+1/2, −z+3/2; (v) −x+1, y+1/2, −z+3/2; (vi) x, y+1, z.
Selected bond lengths (Å) top
Cu1—N12.0367 (19)Cu1—O32.1989 (18)
Cu1—N22.0185 (19)Cu1—O72.0220 (16)
Cu1—O22.0180 (16)Cu1—O82.1537 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O10i0.811.942.748 (3)176
O4—H4A···O6ii0.822.082.681 (3)130
O4—H4A···O7ii0.822.252.997 (3)152
O5—H5A···O2W0.822.212.649 (4)114
O8—H8A···O1Wiii0.811.882.689 (3)175
O9—H9···O2i0.821.912.670 (3)153
O10—H10···O9iv0.822.042.685 (3)135
O1W—H1W···O2Wv0.851.952.790 (3)168
O1W—H2W···O4vi0.852.132.969 (3)170
O2W—H3W···O1ii0.852.022.866 (3)169
O2W—H4W···O50.851.832.649 (4)159
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y−1, z; (iv) −x+2, y+1/2, −z+3/2; (v) −x+1, y+1/2, −z+3/2; (vi) x, y+1, z.
references
References top

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Wang, Q., Li, X., Wang, X. & Zhang, Y. (2007). Acta Cryst. E63, m2537.

Ward, M. D. (2007). Coord. Chem. Rev. 251, 1663–1677.