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

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

doi:10.1107/S1600536808043948

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m151-m152

doi:10.1107/S1600536808043948

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

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

Xiutang Zhang,^a,^c ^* Peihai Wei,^b Jianmin Dou,^c Bin Li ^b and Bo Hu ^b

^aAdvanced Materials Institute of Research, Department of Chemistry and Chemical Engineering, Shandong Institute of Education, Jinan 250013, People's Republic of China, ^bDepartment of Chemistry and Chemical Engineering, Shandong Institute of Education, Jinan 250013, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: xiutangzhang@yahoo.com.cn

(Received 24 December 2008; accepted 25 December 2008; online 8 January 2009)

In the title compound, [Cu(C₁₂H₁₆NO₅)₂]·2H₂O, the Cu^II 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.

Related literature

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

Experimental

Crystal data

[Cu(C₁₂H₁₆NO₅)₂]·2H₂O
M_r = 608.09
Monoclinic, P 2₁ /c
a = 11.9421 (9) Å
b = 11.0238 (9) Å
c = 20.6706 (17) Å
β = 97.462 (1)°
V = 2698.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 293 (2) K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.902, T_max = 0.933
13183 measured reflections
4912 independent reflections
4397 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.117
S = 1.01
4912 reflections
352 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	2.0367 (19)
Cu1—N2	2.0185 (19)
Cu1—O2	2.0180 (16)
Cu1—O3	2.1989 (18)
Cu1—O7	2.0220 (16)
Cu1—O8	2.1537 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O10ⁱ	0.81	1.94	2.748 (3)	176
O4—H4A⋯O6ⁱⁱ	0.82	2.08	2.681 (3)	130
O4—H4A⋯O7ⁱⁱ	0.82	2.25	2.997 (3)	152
O5—H5A⋯O2W	0.82	2.21	2.649 (4)	114
O8—H8A⋯O1Wⁱⁱⁱ	0.81	1.88	2.689 (3)	175
O9—H9⋯O2ⁱ	0.82	1.91	2.670 (3)	153
O10—H10⋯O9^iv	0.82	2.04	2.685 (3)	135
O1W—H1W⋯O2W^v	0.85	1.95	2.790 (3)	168
O1W—H2W⋯O4^vi	0.85	2.13	2.969 (3)	170
O2W—H3W⋯O1ⁱⁱ	0.85	2.02	2.866 (3)	169
O2W—H4W⋯O5	0.85	1.83	2.649 (4)	159
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); 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 global, I. DOI: 10.1107/S1600536808043948/hb2887sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043948/hb2887Isup2.hkl

checkCIF report

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 Cu^II 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%.

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

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]·2H₂O	F(000) = 1276
M_r = 608.09	D_x = 1.497 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4912 reflections
a = 11.9421 (9) Å	θ = 2.1–25.5°
b = 11.0238 (9) Å	µ = 0.88 mm⁻¹
c = 20.6706 (17) Å	T = 293 K
β = 97.462 (1)°	Block, blue
V = 2698.2 (4) Å³	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4912 independent reflections
Radiation source: fine-focus sealed tube	4397 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→11
T_min = 0.902, T_max = 0.933	k = −13→13
13183 measured reflections	l = −25→21

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.076P)² + 1.4852P] where P = (F_o² + 2F_c²)/3
4912 reflections	(Δ/σ)_max = 0.010
352 parameters	Δρ_max = 0.47 e Å⁻³
8 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cu(C₁₂H₁₆NO₅)₂]·2H₂O	V = 2698.2 (4) Å³
M_r = 608.09	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9421 (9) Å	µ = 0.88 mm⁻¹
b = 11.0238 (9) Å	T = 293 K
c = 20.6706 (17) Å	0.12 × 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)
T_min = 0.902, T_max = 0.933	R_int = 0.061
13183 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	8 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	Δρ_max = 0.47 e Å⁻³
4912 reflections	Δρ_min = −0.48 e Å⁻³
352 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
Cu1	0.76750 (2)	0.15964 (2)	0.742179 (13)	0.02060 (12)
C1	0.8354 (4)	0.4629 (4)	0.52078 (18)	0.0604 (10)
H1A	0.9090	0.4980	0.5316	0.091*
H1B	0.7847	0.5226	0.4997	0.091*
H1C	0.8400	0.3953	0.4919	0.091*
C2	0.6893 (2)	0.3686 (2)	0.57268 (13)	0.0304 (6)
C3	0.6096 (3)	0.3782 (3)	0.51893 (14)	0.0448 (8)
H3	0.6257	0.4235	0.4833	0.054*
C4	0.5048 (3)	0.3213 (3)	0.51666 (16)	0.0490 (9)
H4	0.4504	0.3303	0.4805	0.074*
C5	0.4835 (3)	0.2521 (3)	0.56846 (14)	0.0386 (7)
H5	0.4141	0.2132	0.5668	0.058*
C6	0.5636 (2)	0.2380 (2)	0.62432 (12)	0.0250 (5)
C7	0.6687 (2)	0.3017 (2)	0.62939 (11)	0.0212 (5)
C8	0.5359 (2)	0.1518 (2)	0.67278 (13)	0.0245 (5)
H8	0.4620	0.1230	0.6679	0.029*
C9	0.5630 (2)	0.0167 (2)	0.76438 (12)	0.0241 (5)
C10	0.4561 (2)	−0.0514 (2)	0.73731 (14)	0.0328 (6)
H10A	0.4384	−0.1111	0.7689	0.039*
H10B	0.3935	0.0052	0.7301	0.039*
C11	0.5411 (2)	0.0769 (3)	0.82836 (14)	0.0348 (6)
H11A	0.5217	0.0157	0.8587	0.042*
H11B	0.6088	0.1184	0.8480	0.042*
C12	0.6611 (2)	−0.0728 (2)	0.77953 (13)	0.0290 (5)
H12A	0.6453	−0.1287	0.8135	0.035*
H12B	0.6706	−0.1195	0.7408	0.035*
C13	0.6631 (3)	0.4397 (3)	0.97678 (15)	0.0459 (8)
H13A	0.5841	0.4585	0.9684	0.069*
H13B	0.7058	0.5136	0.9827	0.069*
H13C	0.6773	0.3912	1.0156	0.069*
C14	0.8076 (2)	0.3405 (2)	0.92680 (12)	0.0286 (6)
C15	0.8870 (3)	0.3615 (3)	0.97939 (13)	0.0369 (6)
H15	0.8664	0.4006	1.0159	0.044*
C16	0.9992 (3)	0.3245 (3)	0.97888 (13)	0.0362 (6)
H16	1.0529	0.3381	1.0149	0.043*
C17	1.0282 (2)	0.2683 (2)	0.92462 (12)	0.0290 (5)
H17	1.1027	0.2446	0.9240	0.035*
C18	0.9483 (2)	0.2451 (2)	0.86945 (11)	0.0211 (5)
C19	0.8334 (2)	0.2797 (2)	0.86871 (11)	0.0209 (5)
C20	0.9936 (2)	0.1931 (2)	0.81378 (11)	0.0207 (5)
H20	1.0715	0.1824	0.8180	0.025*
C21	0.9988 (2)	0.1161 (2)	0.70679 (11)	0.0205 (5)
C22	1.1144 (2)	0.0571 (2)	0.72962 (12)	0.0261 (5)
H22A	1.1434	0.0190	0.6929	0.031*
H22B	1.1679	0.1186	0.7473	0.031*
C23	1.0162 (2)	0.2241 (2)	0.66108 (11)	0.0254 (5)
H23A	1.0629	0.1980	0.6287	0.031*
H23B	0.9436	0.2487	0.6383	0.031*
C24	0.9245 (2)	0.0216 (2)	0.66761 (12)	0.0241 (5)
H24A	0.9509	0.0087	0.6257	0.029*
H24B	0.9288	−0.0549	0.6909	0.029*
N1	0.60220 (16)	0.11103 (17)	0.72146 (10)	0.0209 (4)
N2	0.93778 (16)	0.16042 (16)	0.75959 (9)	0.0176 (4)
O1	0.79480 (18)	0.4224 (2)	0.57864 (10)	0.0417 (5)
O2	0.74271 (14)	0.30303 (15)	0.68132 (8)	0.0215 (3)
O3	0.76136 (14)	−0.00642 (16)	0.80055 (9)	0.0287 (4)
H3A	0.8136	−0.0541	0.8032	0.043*
O4	0.46929 (17)	−0.11041 (18)	0.67767 (11)	0.0403 (5)
H4A	0.4108	−0.1462	0.6640	0.060*
O5	0.4506 (2)	0.16184 (19)	0.81536 (13)	0.0504 (6)
H5A	0.4388	0.1942	0.8496	0.076*
O6	0.69604 (17)	0.3742 (2)	0.92296 (9)	0.0424 (5)
O7	0.75320 (14)	0.26443 (15)	0.82097 (8)	0.0237 (4)
O8	0.81044 (14)	0.06366 (16)	0.65805 (8)	0.0279 (4)
H8A	0.7676	0.0108	0.6433	0.042*
O9	1.10148 (16)	−0.03065 (18)	0.77788 (10)	0.0378 (5)
H9	1.1627	−0.0622	0.7901	0.057*
O10	1.06809 (16)	0.32536 (16)	0.69565 (9)	0.0316 (4)
H10	1.0280	0.3489	0.7225	0.047*
O1W	0.6645 (2)	0.8968 (2)	0.60223 (11)	0.0496 (6)
H1W	0.6872	0.8234	0.6027	0.074*
H2W	0.6038	0.8985	0.6197	0.074*
O2W	0.2699 (2)	0.1555 (2)	0.87731 (13)	0.0553 (6)
H3W	0.2413	0.0889	0.8885	0.083*
H4W	0.3253	0.1387	0.8565	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02012 (18)	0.01953 (18)	0.02172 (18)	−0.00072 (10)	0.00112 (12)	−0.00073 (10)
C1	0.086 (3)	0.052 (2)	0.051 (2)	−0.0176 (19)	0.0366 (19)	0.0000 (16)
C2	0.0429 (15)	0.0226 (12)	0.0255 (13)	−0.0034 (11)	0.0034 (11)	0.0012 (10)
C3	0.069 (2)	0.0355 (16)	0.0269 (14)	−0.0041 (15)	−0.0042 (14)	0.0095 (12)
C4	0.062 (2)	0.0405 (17)	0.0370 (17)	−0.0055 (15)	−0.0241 (15)	0.0080 (13)
C5	0.0390 (15)	0.0282 (14)	0.0432 (16)	−0.0034 (12)	−0.0149 (13)	0.0016 (12)
C6	0.0266 (12)	0.0197 (12)	0.0268 (12)	0.0017 (10)	−0.0039 (10)	−0.0009 (9)
C7	0.0263 (12)	0.0148 (10)	0.0220 (11)	−0.0004 (9)	0.0015 (9)	−0.0013 (9)
C8	0.0208 (12)	0.0193 (12)	0.0322 (13)	−0.0017 (9)	−0.0008 (10)	−0.0027 (9)
C9	0.0240 (12)	0.0182 (11)	0.0307 (12)	−0.0052 (10)	0.0059 (9)	0.0033 (10)
C10	0.0236 (13)	0.0249 (13)	0.0496 (16)	−0.0065 (10)	0.0040 (11)	0.0050 (12)
C11	0.0392 (15)	0.0314 (14)	0.0372 (15)	−0.0034 (12)	0.0180 (12)	0.0028 (12)
C12	0.0283 (13)	0.0195 (12)	0.0387 (14)	−0.0024 (10)	0.0024 (11)	0.0053 (10)
C13	0.0513 (18)	0.0533 (19)	0.0356 (15)	0.0175 (15)	0.0151 (13)	−0.0120 (14)
C14	0.0338 (14)	0.0300 (14)	0.0223 (12)	0.0064 (11)	0.0047 (10)	−0.0028 (10)
C15	0.0461 (17)	0.0422 (16)	0.0221 (13)	0.0031 (13)	0.0032 (12)	−0.0104 (11)
C16	0.0391 (16)	0.0463 (17)	0.0207 (13)	−0.0032 (13)	−0.0056 (11)	−0.0057 (11)
C17	0.0278 (13)	0.0338 (14)	0.0240 (12)	0.0004 (11)	−0.0019 (10)	0.0005 (10)
C18	0.0243 (12)	0.0198 (11)	0.0193 (11)	−0.0007 (9)	0.0028 (9)	0.0002 (9)
C19	0.0280 (12)	0.0176 (11)	0.0168 (10)	−0.0012 (9)	0.0016 (9)	0.0009 (9)
C20	0.0192 (11)	0.0184 (11)	0.0237 (11)	−0.0006 (9)	0.0002 (9)	0.0008 (9)
C21	0.0219 (11)	0.0188 (11)	0.0213 (11)	−0.0001 (9)	0.0044 (9)	−0.0028 (9)
C22	0.0234 (12)	0.0234 (12)	0.0324 (13)	0.0041 (10)	0.0065 (10)	−0.0009 (10)
C23	0.0303 (13)	0.0243 (12)	0.0230 (11)	−0.0016 (10)	0.0082 (10)	0.0010 (9)
C24	0.0275 (12)	0.0187 (11)	0.0257 (12)	0.0003 (10)	0.0022 (9)	−0.0062 (9)
N1	0.0182 (9)	0.0171 (9)	0.0274 (10)	−0.0011 (8)	0.0031 (8)	−0.0003 (8)
N2	0.0189 (9)	0.0155 (9)	0.0189 (9)	0.0008 (7)	0.0040 (7)	0.0006 (7)
O1	0.0490 (12)	0.0433 (12)	0.0344 (10)	−0.0155 (10)	0.0118 (9)	0.0073 (9)
O2	0.0230 (8)	0.0178 (8)	0.0226 (8)	−0.0040 (7)	−0.0009 (6)	0.0020 (6)
O3	0.0240 (9)	0.0226 (9)	0.0384 (10)	0.0017 (7)	−0.0004 (7)	0.0041 (7)
O4	0.0328 (10)	0.0305 (10)	0.0542 (13)	−0.0085 (8)	−0.0070 (9)	−0.0069 (9)
O5	0.0451 (13)	0.0364 (12)	0.0763 (17)	0.0023 (9)	0.0325 (12)	−0.0080 (11)
O6	0.0365 (11)	0.0621 (14)	0.0288 (10)	0.0173 (10)	0.0040 (8)	−0.0155 (9)
O7	0.0216 (8)	0.0273 (9)	0.0217 (8)	0.0019 (7)	0.0005 (7)	−0.0058 (7)
O8	0.0248 (9)	0.0262 (9)	0.0313 (9)	−0.0020 (7)	−0.0019 (7)	−0.0107 (7)
O9	0.0278 (10)	0.0307 (10)	0.0543 (12)	0.0112 (8)	0.0035 (9)	0.0136 (9)
O10	0.0318 (10)	0.0247 (9)	0.0398 (11)	−0.0078 (7)	0.0103 (8)	−0.0018 (8)
O1W	0.0575 (14)	0.0423 (13)	0.0482 (13)	−0.0186 (11)	0.0043 (10)	−0.0024 (10)
O2W	0.0421 (13)	0.0466 (14)	0.0814 (18)	0.0021 (10)	0.0241 (12)	−0.0010 (12)

Geometric parameters (Å, º) top

Cu1—N1	2.0367 (19)	C13—H13B	0.9600
Cu1—N2	2.0185 (19)	C13—H13C	0.9600
Cu1—O2	2.0180 (16)	C14—C15	1.366 (4)
Cu1—O3	2.1989 (18)	C14—O6	1.376 (3)
Cu1—O7	2.0220 (16)	C14—C19	1.443 (3)
Cu1—O8	2.1537 (17)	C15—C16	1.401 (4)
C1—O1	1.419 (4)	C15—H15	0.9300
C1—H1A	0.9600	C16—C17	1.365 (4)
C1—H1B	0.9600	C16—H16	0.9300
C1—H1C	0.9600	C17—C18	1.412 (3)
C2—C3	1.370 (4)	C17—H17	0.9300
C2—O1	1.383 (3)	C18—C19	1.422 (3)
C2—C7	1.433 (4)	C18—C20	1.452 (3)
C3—C4	1.396 (5)	C19—O7	1.294 (3)
C3—H3	0.9300	C20—N2	1.279 (3)
C4—C5	1.365 (5)	C20—H20	0.9300
C4—H4	0.9300	C21—N2	1.472 (3)
C5—C6	1.409 (4)	C21—C24	1.530 (3)
C5—H5	0.9300	C21—C22	1.544 (3)
C6—C7	1.430 (3)	C21—C23	1.551 (3)
C6—C8	1.450 (4)	C22—O9	1.412 (3)
C7—O2	1.299 (3)	C22—H22A	0.9700
C8—N1	1.278 (3)	C22—H22B	0.9700
C8—H8	0.9300	C23—O10	1.423 (3)
C9—N1	1.481 (3)	C23—H23A	0.9700
C9—C10	1.524 (3)	C23—H23B	0.9700
C9—C12	1.533 (4)	C24—O8	1.428 (3)
C9—C11	1.532 (4)	C24—H24A	0.9700
C10—O4	1.421 (4)	C24—H24B	0.9700
C10—H10A	0.9700	O3—H3A	0.8115
C10—H10B	0.9700	O4—H4A	0.8200
C11—O5	1.428 (4)	O5—H5A	0.8200
C11—H11A	0.9700	O8—H8A	0.8085
C11—H11B	0.9700	O9—H9	0.8200
C12—O3	1.422 (3)	O10—H10	0.8200
C12—H12A	0.9700	O1W—H1W	0.8520
C12—H12B	0.9700	O1W—H2W	0.8511
C13—O6	1.424 (3)	O2W—H3W	0.8541
C13—H13A	0.9600	O2W—H4W	0.8538

O2—Cu1—N2	99.83 (7)	H13A—C13—H13C	109.5
O2—Cu1—O7	91.93 (7)	H13B—C13—H13C	109.5
N2—Cu1—O7	92.43 (7)	C15—C14—O6	124.6 (2)
O2—Cu1—N1	90.88 (7)	C15—C14—C19	122.7 (2)
N2—Cu1—N1	164.82 (7)	O6—C14—C19	112.8 (2)
O7—Cu1—N1	97.97 (7)	C14—C15—C16	120.7 (2)
O2—Cu1—O8	84.98 (7)	C14—C15—H15	119.7
N2—Cu1—O8	78.82 (7)	C16—C15—H15	119.7
O7—Cu1—O8	170.05 (7)	C17—C16—C15	118.9 (2)
N1—Cu1—O8	91.54 (7)	C17—C16—H16	120.6
O2—Cu1—O3	168.97 (6)	C15—C16—H16	120.6
N2—Cu1—O3	90.59 (7)	C16—C17—C18	121.9 (2)
O7—Cu1—O3	91.22 (7)	C16—C17—H17	119.0
N1—Cu1—O3	78.22 (7)	C18—C17—H17	119.0
O8—Cu1—O3	93.58 (7)	C17—C18—C19	120.7 (2)
O1—C1—H1A	109.5	C17—C18—C20	115.4 (2)
O1—C1—H1B	109.5	C19—C18—C20	123.8 (2)
H1A—C1—H1B	109.5	O7—C19—C18	126.2 (2)
O1—C1—H1C	109.5	O7—C19—C14	118.6 (2)
H1A—C1—H1C	109.5	C18—C19—C14	115.2 (2)
H1B—C1—H1C	109.5	N2—C20—C18	126.8 (2)
C3—C2—O1	124.6 (3)	N2—C20—H20	116.6
C3—C2—C7	121.9 (3)	C18—C20—H20	116.6
O1—C2—C7	113.5 (2)	N2—C21—C24	108.05 (19)
C2—C3—C4	121.2 (3)	N2—C21—C22	114.98 (19)
C2—C3—H3	119.4	C24—C21—C22	108.01 (19)
C4—C3—H3	119.4	N2—C21—C23	108.37 (18)
C5—C4—C3	118.9 (3)	C24—C21—C23	108.33 (19)
C5—C4—H4	120.6	C22—C21—C23	108.92 (19)
C3—C4—H4	120.6	O9—C22—C21	109.19 (19)
C4—C5—C6	121.9 (3)	O9—C22—H22A	109.8
C4—C5—H5	119.0	C21—C22—H22A	109.8
C6—C5—H5	119.1	O9—C22—H22B	109.8
C5—C6—C7	120.1 (2)	C21—C22—H22B	109.8
C5—C6—C8	116.5 (2)	H22A—C22—H22B	108.3
C7—C6—C8	123.3 (2)	O10—C23—C21	112.36 (19)
O2—C7—C6	124.2 (2)	O10—C23—H23A	109.1
O2—C7—C2	120.0 (2)	C21—C23—H23A	109.1
C6—C7—C2	115.8 (2)	O10—C23—H23B	109.1
N1—C8—C6	126.9 (2)	C21—C23—H23B	109.1
N1—C8—H8	116.6	H23A—C23—H23B	107.9
C6—C8—H8	116.6	O8—C24—C21	109.23 (18)
N1—C9—C10	116.2 (2)	O8—C24—H24A	109.8
N1—C9—C12	106.37 (19)	C21—C24—H24A	109.8
C10—C9—C12	109.9 (2)	O8—C24—H24B	109.8
N1—C9—C11	108.37 (19)	C21—C24—H24B	109.8
C10—C9—C11	107.6 (2)	H24A—C24—H24B	108.3
C12—C9—C11	108.3 (2)	C8—N1—C9	120.4 (2)
O4—C10—C9	111.2 (2)	C8—N1—Cu1	123.88 (17)
O4—C10—H10A	109.4	C9—N1—Cu1	115.57 (15)
C9—C10—H10A	109.4	C20—N2—C21	119.4 (2)
O4—C10—H10B	109.4	C20—N2—Cu1	123.80 (16)
C9—C10—H10B	109.4	C21—N2—Cu1	116.77 (14)
H10A—C10—H10B	108.0	C2—O1—C1	117.8 (2)
O5—C11—C9	109.3 (2)	C7—O2—Cu1	122.38 (14)
O5—C11—H11A	109.8	C12—O3—Cu1	110.35 (14)
C9—C11—H11A	109.8	C12—O3—H3A	107.2
O5—C11—H11B	109.8	Cu1—O3—H3A	119.7
C9—C11—H11B	109.8	C10—O4—H4A	109.5
H11A—C11—H11B	108.3	C11—O5—H5A	109.5
O3—C12—C9	108.8 (2)	C14—O6—C13	117.1 (2)
O3—C12—H12A	109.9	C19—O7—Cu1	123.85 (15)
C9—C12—H12A	109.9	C24—O8—Cu1	111.75 (13)
O3—C12—H12B	109.9	C24—O8—H8A	111.3
C9—C12—H12B	109.9	Cu1—O8—H8A	117.0
H12A—C12—H12B	108.3	C22—O9—H9	109.5
O6—C13—H13A	109.5	C23—O10—H10	109.5
O6—C13—H13B	109.5	H1W—O1W—H2W	107.6
H13A—C13—H13B	109.5	H3W—O2W—H4W	108.2
O6—C13—H13C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O10ⁱ	0.81	1.94	2.748 (3)	176
O4—H4A···O6ⁱⁱ	0.82	2.08	2.681 (3)	130
O4—H4A···O7ⁱⁱ	0.82	2.25	2.997 (3)	152
O5—H5A···O2W	0.82	2.21	2.649 (4)	114
O8—H8A···O1Wⁱⁱⁱ	0.81	1.88	2.689 (3)	175
O9—H9···O2ⁱ	0.82	1.91	2.670 (3)	153
O10—H10···O9^iv	0.82	2.04	2.685 (3)	135
O1W—H1W···O2W^v	0.85	1.95	2.790 (3)	168
O1W—H2W···O4^vi	0.85	2.13	2.969 (3)	170
O2W—H3W···O1ⁱⁱ	0.85	2.02	2.866 (3)	169
O2W—H4W···O5	0.85	1.83	2.649 (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.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₂H₁₆NO₅)₂]·2H₂O
M_r	608.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.9421 (9), 11.0238 (9), 20.6706 (17)
β (°)	97.462 (1)
V (Å³)	2698.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.902, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	13183, 4912, 4397
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.01
No. of reflections	4912
No. of parameters	352
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.48

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—N1	2.0367 (19)	Cu1—O3	2.1989 (18)
Cu1—N2	2.0185 (19)	Cu1—O7	2.0220 (16)
Cu1—O2	2.0180 (16)	Cu1—O8	2.1537 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O10ⁱ	0.81	1.94	2.748 (3)	176
O4—H4A···O6ⁱⁱ	0.82	2.08	2.681 (3)	130
O4—H4A···O7ⁱⁱ	0.82	2.25	2.997 (3)	152
O5—H5A···O2W	0.82	2.21	2.649 (4)	114
O8—H8A···O1Wⁱⁱⁱ	0.81	1.88	2.689 (3)	175
O9—H9···O2ⁱ	0.82	1.91	2.670 (3)	153
O10—H10···O9^iv	0.82	2.04	2.685 (3)	135
O1W—H1W···O2W^v	0.85	1.95	2.790 (3)	168
O1W—H2W···O4^vi	0.85	2.13	2.969 (3)	170
O2W—H3W···O1ⁱⁱ	0.85	2.02	2.866 (3)	169
O2W—H4W···O5	0.85	1.83	2.649 (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.

Acknowledgements

The authors thank the National Ministry of Science and Technology of China (grant No. 2001CB6105-07) for support.

References

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Q., Li, X., Wang, X. & Zhang, Y. (2007). Acta Cryst. E63, m2537. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ward, M. D. (2007). Coord. Chem. Rev. 251, 1663–1677. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 2| February 2009| Pages m151-m152

doi:10.1107/S1600536808043948

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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