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

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ISSN: 2056-9890

N,N′-Di­methyl­ethylenedi­ammonium dioxalatocuprate(II)

aDépartement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and bSciences et Méthodes Séparatives, UPRES EA 3233 IMR, IRCOF, F-76821, Mont-Saint-Aigan, Université de Rouen Cedex, France
*Correspondence e-mail: mlgayeastou@yahoo.fr

(Received 20 June 2011; accepted 29 June 2011; online 9 July 2011)

The asymmetric unit of the title salt, (C4H14N2)[Cu(C2O4)2], consists of one complex anion and two cationic half-mol­ecules, the other halves being generated by inversion symmetry. The CuII atom in the anion is coordinated by two bidentate oxalate ligands in a distorted square-planar geometry. Inter­molecular hydrogen bonds, involving the NH groups as donors and O atoms as acceptors, are observed, which lead to the formation of a three-dimensional network structure.

Related literature

For background to decomposition reactions leading to oxalate anions, see: Kelly et al. (2005[Kelly, T. L., Milway, V. A., Grove, H., Niel, V., Abedin, T. S. M., Thompson, L. K., Zhao, L., Harvey, R. G., Miller, D. O., Leech, M., Goeta, A. E. & Howard, J. A. K. (2005). Polyhedron, 24, 807-821.]); Diallo et al. (2008[Diallo, M., Tamboura, F. B., Gaye, M., Barry, A. H. & Bah, Y. (2008). Acta Cryst. E64, m1124-m1125.]). For related structures, see: Androš et al. (2010[Androš, L., Jurić, M., Planinić, P., Žilić, D., Rakvin, B. & Molčanov, K. (2010). Polyhedron, 29, 1291-1298.]); Fan et al. (2001[Fan, J., Sun, W.-Y., Okamura, T.-A., Yu, K.-B. & Ueyama, N. (2001). Inorg. Chim. Acta, 319, 240-246.]); Zhang et al. (2009[Zhang, L.-J., Shen, X.-C. & Liang, H. (2009). Acta Cryst. E65, m1276-m1277.]).

[Scheme 1]

Experimental

Crystal data
  • (C4H14N2)[Cu(C2O4)2]

  • Mr = 329.75

  • Triclinic, [P \overline 1]

  • a = 5.7734 (5) Å

  • b = 8.4127 (7) Å

  • c = 12.5623 (11) Å

  • α = 90.443 (1)°

  • β = 100.715 (1)°

  • γ = 107.188 (1)°

  • V = 571.46 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.95 mm−1

  • T = 293 K

  • 0.15 × 0.13 × 0.10 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 4558 measured reflections

  • 2292 independent reflections

  • 2192 reflections with I > 2σ(I)

  • Rint = 0.014

Refinement
  • R[F2 > 2σ(F2)] = 0.024

  • wR(F2) = 0.07

  • S = 1.12

  • 2292 reflections

  • 174 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Selected bond lengths (Å)

Cu1—O1 1.9128 (13)
Cu1—O2 1.9163 (13)
Cu1—O2A 1.9184 (13)
Cu1—O1A 1.9572 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1S—H2S1⋯O3Ai 0.90 2.22 2.939 (2) 137
N1S—H2S2⋯O1Aii 0.90 2.13 3.018 (2) 169
N2S—H4S1⋯O4Aii 0.90 2.15 2.939 (2) 145
N2S—H4S1⋯O3Aii 0.90 2.31 3.004 (2) 134
N2S—H4S2⋯O4iii 0.90 2.11 2.861 (2) 140
N2S—H4S2⋯O3iv 0.90 2.58 3.131 (2) 120
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y, -z; (iii) x-1, y, z; (iv) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2001[Bruker. (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1999[Bruker. (1999). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The title salt, (C4H14N2)[Cu(C2O4)2], was obtained as an unexpected product by reaction of the employed ligand (C6H10N2O2)n, in a methanolic medium. The hydrolytically unstable cyclic ligand apparently is oxidatively hydrolyzed in the presence of metal ions, leading to the oxalate dianion (Diallo et al., 2008; Kelly et al., 2005). This species, which is generated in situ, acts with copper(II) ions resulting in the formation of the title compound. A similar reaction was found elsewhere (Zhang et al., 2009).

The structure exhibits an ion-pair complex comprising two cationic half-molecules (the other halves being generated by inversion symmetry) and a [Cu(C2O4)2]2- dianion (Fig. 1). The CuII ion is four-coordinated in a slightly distorted square–planar CuO4 environment, comprising four O donor atoms from two oxalate ligands [Cu–O, 1.9128 (13), 1.9163 (13), 1.9184 (13) and 1.9572 (13) Å]. The O(1)—Cu—O(2 A) and O(2)—Cu—O(1 A) angles are 179.52 (5) and 178.10 (5)°, respectively, which are slightly smaller than those observed in the complex [K2Cu(ox)2].4H2O (180 °), where ox is oxalate (Fan et al., 2001). The other two oxygen atoms of each oxalate group are not involved in coordination. The two oxalate anions deviate slightly from planarity, with torsion angles of O(1)—C(1)—C(2)—O(2), O(4)—C(1)—C(2)—O(3), O(1A)—C(1A)—C(2A)—O(2A) and O(4A)—C(1A)—C(2A)—O(3A) -2.5 (2), -3.4 (3), 2.8 (2) and 3.8 (2)°, respectively. These values are similar to those found in [Cu(bpy)(C2O4)(H2O)].H2C2O4 (Androš et al., 2010), where bpy is bipyridine.

N—H···O hydrogen-bonding interactions, part of which are bifurcated, between the cations and the complex anions lead to the formation of a three-dimensional network structure (Table 2; Figs. 2, 3).

Related literature top

For background to decomposition reactions leading to oxalate anions, see: Kelly et al. (2005); Diallo et al. (2008). For related structures, see: Androš et al. (2010); Fan et al. (2001); Zhang et al. (2009).

Experimental top

In a 50 ml round bottom flask dimethyl oxalate (2.36 g, 0.020 mol), dissolved in ethanol (10 ml), was reacted with N,N'-dimethyl-1,2-diaminoethane (1.77 g, 0.020 mol) in ethanol (10 ml), to yield immediately a quantitative precipitate. The white solid formed was separated by filtration, washed with methanol and ether and dried under vacuum (yield 3.32 g, 58.5%); m.p.= 513 K. 1 H NMR in CDCl3, δ (p.p.m.): 3.1, s, 12H, –CH3; 3.5, s, 8H, –CH2–. 13C NMR in CDCl3, δ (p.p.m.): 34.86, N—CH3, 46.12, N—CH2, 157.56, C=O. IR (cm-1) 1598 (C=O), 1284 (C—N). Anal. Calc. for C12H20N4O4 (%): C, 50.62; H, 7.11; N, 19.68. Found: C, 50.60; H, 7.09; N, 19.71. Mass spectrum (m/z) 284, 162, 134, 106, 78. Into a methanolic solution (5 ml) of copper chloride dihydrate (0.2131 g, 1.25 mmol) was added a methanolic solution (10 ml) of the ligand prepared as described above (0.3554 g, 1.25 mmol). The resulting mixture was heated at 333 K for thirty minutes. The green solution was filtered and then allowed to evaporate slowly in open atmosphere. After one week, blue crystals suitable for X-ray analysis were obtained. The crystals were separated, washed with cold methanol and dried (yield: 65%); Anal. Calc. for (C4H14N2)[Cu(C2O4)2](%): C, 29.14; H, 4.28; N, 8.50. Found: C, 29.16; H, 4.26; N, 8.46. Selected IR data (cm-1, KBr pellet): 3300, 1637, 1600, 1582, 1197, 764.

Refinement top

All H atoms were located from the Fourier electron density maps, then placed according to their geometrical environment and refined isotropically. They were refined using a riding model with 0.96 Å for methyl H atoms and Uiso(H) = 1.5Ueq(C), with 0.97 Å for methylene H atoms and Uiso(H) = 1.2Ueq(C), and with 0.90 Å for ammonium H atoms and Uiso(H) = 1.2Ueq(N). In addition, a rotating-group model was applied for methyl groups.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. An ORTEP view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are plotted at the 50% probability level. [Symmetry codes: *) -x + 1, -y + 1, -z; **) -x + 1, -y, -z + 1].
[Figure 2] Fig. 2. Projection of the structure along the b axis showing the anions connected by organics cations. Broken lines stand for hydrogen bonds.
[Figure 3] Fig. 3. Projection of the structure along the a axis showing the anions connected by organics cations. Broken lines stand for hydrogen bonds.
N,N'-Dimethylethylenediammonium dioxalatocuprate(II) top
Crystal data top
(C4H14N2)[Cu(C2O4)2]Z = 2
Mr = 329.75F(000) = 338
Triclinic, P1Dx = 1.916 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7734 (5) ÅCell parameters from 2192 reflections
b = 8.4127 (7) Åθ = 1.7–26.4°
c = 12.5623 (11) ŵ = 1.95 mm1
α = 90.443 (1)°T = 293 K
β = 100.715 (1)°Prism, blue
γ = 107.188 (1)°0.15 × 0.13 × 0.10 mm
V = 571.46 (8) Å3
Data collection top
Bruker SMART CCD
diffractometer
Rint = 0.014
Graphite monochromatorθmax = 26.4°, θmin = 1.7°
ω scansh = 77
4558 measured reflectionsk = 1010
2292 independent reflectionsl = 1515
2192 reflections with I > 2σ(I)
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)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.07H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0412P)2 + 0.2106P]
where P = (Fo2 + 2Fc2)/3
2292 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
(C4H14N2)[Cu(C2O4)2]γ = 107.188 (1)°
Mr = 329.75V = 571.46 (8) Å3
Triclinic, P1Z = 2
a = 5.7734 (5) ÅMo Kα radiation
b = 8.4127 (7) ŵ = 1.95 mm1
c = 12.5623 (11) ÅT = 293 K
α = 90.443 (1)°0.15 × 0.13 × 0.10 mm
β = 100.715 (1)°
Data collection top
Bruker SMART CCD
diffractometer
2192 reflections with I > 2σ(I)
4558 measured reflectionsRint = 0.014
2292 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.07H-atom parameters constrained
S = 1.12Δρmax = 0.35 e Å3
2292 reflectionsΔρmin = 0.43 e Å3
174 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
xyzUiso*/Ueq
Cu10.81900 (4)0.08511 (2)0.071311 (15)0.02027 (10)
O10.7688 (2)0.09898 (16)0.16179 (10)0.0236 (3)
O20.9414 (3)0.22323 (16)0.20393 (11)0.0273 (3)
O30.9874 (3)0.1983 (2)0.38225 (12)0.0400 (4)
O40.8221 (3)0.14792 (19)0.33674 (12)0.0346 (3)
O1A0.7045 (2)0.05261 (16)0.06558 (10)0.0244 (3)
O2A0.8699 (3)0.27099 (16)0.01838 (11)0.0274 (3)
O3A0.7987 (3)0.32433 (18)0.19228 (12)0.0325 (3)
O4A0.6466 (2)0.01666 (17)0.24263 (10)0.0271 (3)
C10.8324 (3)0.0538 (2)0.26338 (15)0.0230 (4)
C20.9307 (3)0.1394 (2)0.28879 (15)0.0249 (4)
C1A0.7074 (3)0.0373 (2)0.14883 (14)0.0201 (3)
C2A0.8000 (3)0.2289 (2)0.11968 (15)0.0221 (4)
C1S0.5705 (4)0.5131 (2)0.05810 (18)0.0323 (4)
H1S10.71610.47640.06310.039*
H1S20.62440.63090.08090.039*
N1S0.4111 (3)0.4180 (2)0.13069 (15)0.0328 (4)
H2S10.27850.45470.12720.039*
H2S20.35640.30940.10740.039*
C2S0.4947 (4)0.0903 (3)0.50540 (16)0.0302 (4)
H3S10.64870.10560.49410.036*
H3S20.47370.12130.5780.036*
N2S0.2872 (3)0.1980 (2)0.42503 (13)0.0329 (4)
H4S10.3130.17310.35780.039*
H4S20.14670.1770.43240.039*
C3S0.5449 (4)0.4354 (3)0.24519 (18)0.0394 (5)
H1S30.68050.38990.250.059*
H1S40.4340.37620.28980.059*
H1S50.60690.55120.26980.059*
C4S0.2574 (5)0.3766 (3)0.4373 (2)0.0484 (6)
H2S30.40750.39930.43030.073*
H2S40.1240.44170.3820.073*
H2S50.22130.40510.50750.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02469 (14)0.01821 (14)0.01732 (14)0.00556 (9)0.00424 (9)0.00003 (9)
O10.0270 (7)0.0220 (6)0.0214 (6)0.0065 (5)0.0054 (5)0.0008 (5)
O20.0344 (7)0.0231 (6)0.0228 (7)0.0070 (6)0.0046 (5)0.0023 (5)
O30.0505 (9)0.0451 (9)0.0212 (7)0.0126 (7)0.0027 (6)0.0065 (6)
O40.0398 (8)0.0394 (8)0.0268 (7)0.0139 (7)0.0089 (6)0.0120 (6)
O1A0.0326 (7)0.0193 (6)0.0194 (6)0.0060 (5)0.0034 (5)0.0003 (5)
O2A0.0389 (8)0.0198 (6)0.0229 (7)0.0069 (6)0.0075 (6)0.0005 (5)
O3A0.0419 (8)0.0299 (7)0.0280 (7)0.0139 (6)0.0071 (6)0.0104 (6)
O4A0.0284 (7)0.0331 (7)0.0189 (7)0.0097 (6)0.0022 (5)0.0022 (5)
C10.0189 (8)0.0285 (9)0.0243 (9)0.0101 (7)0.0063 (7)0.0032 (7)
C20.0221 (9)0.0290 (9)0.0236 (9)0.0092 (7)0.0024 (7)0.0032 (7)
C1A0.0160 (8)0.0235 (9)0.0226 (9)0.0084 (7)0.0047 (6)0.0006 (7)
C2A0.0212 (8)0.0224 (8)0.0254 (9)0.0095 (7)0.0063 (7)0.0033 (7)
C1S0.0270 (10)0.0234 (9)0.0457 (12)0.0029 (8)0.0135 (9)0.0064 (8)
N1S0.0272 (8)0.0244 (8)0.0462 (10)0.0054 (7)0.0098 (7)0.0023 (7)
C2S0.0294 (10)0.0409 (12)0.0210 (9)0.0130 (9)0.0028 (7)0.0028 (8)
N2S0.0340 (9)0.0379 (9)0.0244 (8)0.0084 (7)0.0039 (7)0.0050 (7)
C3S0.0414 (12)0.0311 (11)0.0445 (13)0.0124 (9)0.0032 (10)0.0025 (9)
C4S0.0696 (17)0.0385 (12)0.0354 (12)0.0118 (12)0.0131 (11)0.0060 (10)
Geometric parameters (Å, º) top
Cu1—O11.9128 (13)C1S—H1S20.97
Cu1—O21.9163 (13)N1S—C3S1.485 (3)
Cu1—O2A1.9184 (13)N1S—H2S10.90
Cu1—O1A1.9572 (13)N1S—H2S20.90
O1—C11.282 (2)C2S—N2S1.473 (3)
O2—C21.284 (2)C2S—C2Sii1.511 (4)
O3—C21.218 (2)C2S—H3S10.97
O4—C11.218 (2)C2S—H3S20.97
O1A—C1A1.295 (2)N2S—C4S1.474 (3)
O2A—C2A1.275 (2)N2S—H4S10.90
O3A—C2A1.220 (2)N2S—H4S20.90
O4A—C1A1.209 (2)C3S—H1S30.96
C1—C21.564 (3)C3S—H1S40.96
C1A—C2A1.558 (2)C3S—H1S50.96
C1S—N1S1.486 (3)C4S—H2S30.96
C1S—C1Si1.513 (4)C4S—H2S40.96
C1S—H1S10.97C4S—H2S50.96
O1—Cu1—O285.90 (5)C3S—N1S—H2S1109.2
O1—Cu1—O2A179.52 (5)C1S—N1S—H2S1109.2
O2—Cu1—O2A93.63 (6)C3S—N1S—H2S2109.2
O1—Cu1—O1A95.12 (5)C1S—N1S—H2S2109.2
O2—Cu1—O1A178.10 (5)H2S1—N1S—H2S2107.9
O2A—Cu1—O1A85.36 (5)N2S—C2S—C2Sii110.15 (19)
C1—O1—Cu1113.02 (11)N2S—C2S—H3S1109.6
C2—O2—Cu1112.98 (12)C2Sii—C2S—H3S1109.6
C1A—O1A—Cu1111.82 (11)N2S—C2S—H3S2109.6
C2A—O2A—Cu1113.52 (11)C2Sii—C2S—H3S2109.6
O4—C1—O1125.29 (18)H3S1—C2S—H3S2108.1
O4—C1—C2120.57 (17)C2S—N2S—C4S112.34 (17)
O1—C1—C2114.14 (15)C2S—N2S—H4S1109.1
O3—C2—O2125.64 (18)C4S—N2S—H4S1109.1
O3—C2—C1120.45 (17)C2S—N2S—H4S2109.1
O2—C2—C1113.90 (15)C4S—N2S—H4S2109.1
O4A—C1A—O1A125.21 (17)H4S1—N2S—H4S2107.9
O4A—C1A—C2A120.46 (16)N1S—C3S—H1S3109.5
O1A—C1A—C2A114.33 (15)N1S—C3S—H1S4109.5
O3A—C2A—O2A125.78 (17)H1S3—C3S—H1S4109.5
O3A—C2A—C1A119.40 (17)N1S—C3S—H1S5109.5
O2A—C2A—C1A114.82 (15)H1S3—C3S—H1S5109.5
N1S—C1S—C1Si110.2 (2)H1S4—C3S—H1S5109.5
N1S—C1S—H1S1109.6N2S—C4S—H2S3109.5
C1Si—C1S—H1S1109.6N2S—C4S—H2S4109.5
N1S—C1S—H1S2109.6H2S3—C4S—H2S4109.5
C1Si—C1S—H1S2109.6N2S—C4S—H2S5109.5
H1S1—C1S—H1S2108.1H2S3—C4S—H2S5109.5
C3S—N1S—C1S112.06 (16)H2S4—C4S—H2S5109.5
O2—Cu1—O1—C10.30 (12)O1—C1—C2—O3176.97 (17)
O1A—Cu1—O1—C1178.68 (12)O4—C1—C2—O2177.15 (17)
O1—Cu1—O2—C21.77 (13)O1—C1—C2—O22.5 (2)
O2A—Cu1—O2—C2178.14 (13)Cu1—O1A—C1A—O4A179.71 (14)
O1—Cu1—O1A—C1A178.09 (11)Cu1—O1A—C1A—C2A0.11 (17)
O2A—Cu1—O1A—C1A1.83 (12)Cu1—O2A—C2A—O3A175.09 (15)
O2—Cu1—O2A—C2A178.11 (13)Cu1—O2A—C2A—C1A4.23 (19)
O1A—Cu1—O2A—C2A3.51 (13)O4A—C1A—C2A—O3A3.8 (3)
Cu1—O1—C1—O4178.63 (15)O1A—C1A—C2A—O3A176.58 (16)
Cu1—O1—C1—C20.99 (18)O4A—C1A—C2A—O2A176.83 (16)
Cu1—O2—C2—O3176.78 (17)O1A—C1A—C2A—O2A2.8 (2)
Cu1—O2—C2—C12.64 (19)C1Si—C1S—N1S—C3S178.0 (2)
O4—C1—C2—O33.4 (3)C2Sii—C2S—N2S—C4S175.9 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1S—H2S1···O3Ai0.902.222.939 (2)137
N1S—H2S2···O1Aiii0.902.133.018 (2)169
N2S—H4S1···O4Aiii0.902.152.939 (2)145
N2S—H4S1···O3Aiii0.902.313.004 (2)134
N2S—H4S2···O4iv0.902.112.861 (2)140
N2S—H4S2···O3ii0.902.583.131 (2)120
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z+1; (iii) x+1, y, z; (iv) x1, y, z.

Experimental details

Crystal data
Chemical formula(C4H14N2)[Cu(C2O4)2]
Mr329.75
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.7734 (5), 8.4127 (7), 12.5623 (11)
α, β, γ (°)90.443 (1), 100.715 (1), 107.188 (1)
V3)571.46 (8)
Z2
Radiation typeMo Kα
µ (mm1)1.95
Crystal size (mm)0.15 × 0.13 × 0.10
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4558, 2292, 2192
Rint0.014
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.07, 1.12
No. of reflections2292
No. of parameters174
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.43

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 1999), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
Cu1—O11.9128 (13)Cu1—O2A1.9184 (13)
Cu1—O21.9163 (13)Cu1—O1A1.9572 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1S—H2S1···O3Ai0.902.222.939 (2)137
N1S—H2S2···O1Aii0.902.133.018 (2)169
N2S—H4S1···O4Aii0.902.152.939 (2)145
N2S—H4S1···O3Aii0.902.313.004 (2)134
N2S—H4S2···O4iii0.902.112.861 (2)140
N2S—H4S2···O3iv0.902.583.131 (2)120
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x1, y, z; (iv) x+1, y, z+1.
 

Acknowledgements

The authors thank the Agence Universitaire de la Francophonie for financial support (AUF-PSCI No.6314PS804).

References

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