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The title compound, [Cu2(OH)2(C12H8N2)2(H2O)2][Cu(C10H9NO5S)2]·6H2O, is comprised of a copper-centred complex cation and a copper-centred complex anion; the cation lies about an inversion centre and in the anion the Cu atom lies on an inversion centre. In the doubly charged bridged dicopper cation, each Cu centre has distorted square-pyramidal geometry. In the square-planar dianion, two sulfonate ligands are trans coordinated to the Cu atom via a deprotonated hydroxyl O atom and an imine N atom, forming two six-membered chelate rings. The structure is stabilized by an extensive hydrogen-bond system and aromatic-ring stacking interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104021468/ta1454sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104021468/ta1454Isup2.hkl
Contains datablock I

CCDC reference: 254918

Comment top

Schiff base complexes containing S, and complexes of amino acid Schiff bases (Casella & Gullotti, 1981, 1986; Wang et al., 1994), have recently aroused increased interest because of their antiviral, anticancer and antibacterial activities. Taurine, an amino acid containing S, is indispensable to human life and has important physiological functions. Recently, we have found that the Schiff base derived from taurine has manifold coordination modes (Zeng et al., 2003; Jiang et al., 2003). Aromatic-ring stacking interactions are an important characteristic of ternary complexes and have important functions, such as stabilizing the double-helix structure of DNA (Frieden, 1975) and the interactions between anticancer drugs and DNA (Hollis et al., 1989). We report here the synthesis and crystal structure of the title novel copper(II) complex, (I), prepared by the reaction of CuSO4·5H2O, the potassium salt of the Schiff base ligand 2-{[(E)-(2-hydroxy-5{[(2-sulfoethyl)imino]methyl}phenyl)methylidene]amino}-1- ethanesulfonic acid, derived in turn by the reaction of taurine and 5-formyl- salicylaldehyde, and 1,10-phenanthroline (Phen). \sch

Compound (I) is comprised of a Cu-centred complex cation and anion, both of which are centrosymmetric (Fig. 1). The doubly-charged bridged dicopper cation, in which each Cu centre has distorted square-pyramidal geometry, occurs in five previously published crystal structures (Cambridge Structural Database, Version 5.0, July 2004 release; Allen, 2002). In all of these examples, the ions are also centrosymmetric. The geometry of the cation in (I) is similar to that in the other examples. In the dinegative square-planar anion, two sulfonate ligands are each trans coordinated to Cu via a deprotonated hydroxyl O atom and the imine N atom, to form two six-membered chelate rings (Table 2). There may be a weak interaction between atoms Cu1 and O2 [3.194 (4) Å] of adjacent anions in the fifth and sixth quasi-octahedral positions (Fig. 2). The sulfonate group itself is not coordinated to Cu but is packed in the crystal structure to form hydrogen-bonds by which the group is stabilized.

There are a number of hydrogen bonds in (I) (Fig.2). The anion and cation, which are attracted to each other by electrostatic forces, are also linked by hydrogen bonds between atoms O6 and O5i, and O7 and O4i [symmetry code: (i) −x, 1 − y, 1 − z]. Other hydrogen bonds are listed in Table 2. The O8···O4i distance of 2.862 (5) Å, O8···O10ii distance of 2.702 (8) Å and O8···O8ii distance of 2.569 (7) Å indicate that there may be possible hydrogen-bond interactions involving these water molecules and the sulfonate group [symmetry code: (ii) 1 − x, 2 − y, 2 − z]. These bonds form a hydrogen-bond network, which extends along the ac plane of the cell and links the cation and anion to form a two-dimensional network. Also, two sulfonate groups of the anion stretch to two adjacent ac planes to form hydrogen bonds. Thus, the network is extended to a three-dimensional structure.

Anions and cations are arranged in alternate layers parallel to the ab plane (Fig. 2). Both the anion and cation have two independent aromatic rings. The anion uses one of its benzene (B) rings and the cation uses one of its Phen (P) rings to take part in ππ stacking interactions, forming infinite columns along the c axis (Fig. 3). In each cell, the aromatic rings stack in the column in the sequence P—B—B—P. The other aromatic rings of each anion and cation take part in the stacking of four adjacent columns, thus forming a three-dimensional structure. The dihedral angle and average distance between P and B rings are 3.52 (11)° and 3.348 Å, respectively. The two B rings are parallel, with an average distance of 3.362 Å, while the two P rings in two adjacent cells are also parallel, with an average distance of 3.429 Å. The structure of (I) is thus stabilized by this hydrogen-bond system and these aromatic-ring stacking interactions.

Experimental top

The potassium salt of the Schiff base ligand 2-{[(E)-(2-hydroxy-5{[(2-sulfoethyl)imino]methyl}phenyl)methylidene]amino}-1- ethanesulfonic acid, L, was synthesized as given by Zeng et al. (2003). The ligand Or salt? (1.0 mmol) was dissolved in aqueous methanol (25 ml). To this solution, CuSO4·5H2O (1.0 mmol) was added, and the mixture was stirred and refluxed at 323 K for 6 h. 1,10-Phenanthroline (1.0 mmol) was then added and the reaction continued for another 6 h. After cooling to room temperature and subsequent filtration, the filtrate was left to stand at room temperature. Dark-green crystals of (I) suitable for X-ray diffraction were obtained in a yield of 40%. Analysis, found: C 42.87, H 4.21, N 6.56%; C44H52Cu3N6O20S2 requires: C 42.59, H 4.19, N 6.78%. IR (KBr, ν, cm−1): 1032.0, 1037.0, 1160.2, 1185.0 (–SO3), 1618.5 (CN), 1601.7, 1522.3 (CN + CC), 3419.7 (O—H).

Refinement top

The H atoms of atoms O6, O7 and O9, and one H atom of O10, were located in a difference Fourier map and their positions and isotropic displacement parameters were refined, with the O—H distance constrained in the range of 0.813–0.844 Å. All other H atoms were positioned geometrically and were treated as riding atoms and refined isotropically, with C—H distances of 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The components of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omittted for clarity.
[Figure 2] Fig. 2. A perspective drawing of (I). H atoms have been omitted for clarity, except those involved in hydrogen-bond interactions. Hydrogen bonds are indicated by dashed lines. The quasi-octahedral interactions (see text) are indicated by dotted lines.
[Figure 3] Fig. 3. A perspective view of the aromatic-ring interactions in (I). Only the aromatic rings and the Cu atoms are included.
Di-µ-hydroxo-bis[aqua(1,10-phenanthroline-κ2N,N')copper(II)] trans-bis(2-{[(E)-(5-formyl-2- oxido-κO-phenyl)methylidene]amino-κN}ethanesulfonato(2-))copper(II) hexahydrate top
Crystal data top
[Cu2(OH)2(C12H8N2)2(H2O)2][Cu(C10H9NO5S)2]·6H2OZ = 1
Mr = 1239.66F(000) = 637
Triclinic, P1Dx = 1.664 Mg m3
a = 9.370 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.793 (2) ÅCell parameters from 35 reflections
c = 13.860 (4) Åθ = 2.6–18.7°
α = 98.02 (2)°µ = 1.45 mm1
β = 93.61 (3)°T = 296 K
γ = 99.63 (2)°Block, green
V = 1236.8 (5) Å30.48 × 0.38 × 0.34 mm
Data collection top
Siemens P4
diffractometer
3411 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.011
Graphite monochromatorθmax = 25.3°, θmin = 1.5°
ω scansh = 011
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1111
Tmin = 0.531, Tmax = 0.611l = 1616
4950 measured reflections3 standard reflections every 97 reflections
4476 independent reflections intensity decay: 2.1%
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.112P]
where P = (Fo2 + 2Fc2)/3
4476 reflections(Δ/σ)max = 0.001
364 parametersΔρmax = 0.61 e Å3
8 restraintsΔρmin = 0.44 e Å3
Crystal data top
[Cu2(OH)2(C12H8N2)2(H2O)2][Cu(C10H9NO5S)2]·6H2Oγ = 99.63 (2)°
Mr = 1239.66V = 1236.8 (5) Å3
Triclinic, P1Z = 1
a = 9.370 (2) ÅMo Kα radiation
b = 9.793 (2) ŵ = 1.45 mm1
c = 13.860 (4) ÅT = 296 K
α = 98.02 (2)°0.48 × 0.38 × 0.34 mm
β = 93.61 (3)°
Data collection top
Siemens P4
diffractometer
3411 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Rint = 0.011
Tmin = 0.531, Tmax = 0.6113 standard reflections every 97 reflections
4950 measured reflections intensity decay: 2.1%
4476 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0348 restraints
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.61 e Å3
4476 reflectionsΔρmin = 0.44 e Å3
364 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
Cu10.00000.50000.50000.03515 (16)
Cu20.50628 (4)0.86334 (4)0.94564 (3)0.02735 (12)
S0.12598 (10)0.01359 (9)0.27374 (7)0.0468 (3)
O10.1750 (3)0.5995 (2)0.57032 (18)0.0478 (6)
O20.8170 (3)0.5142 (4)0.6868 (3)0.0911 (11)
O30.0664 (4)0.0983 (3)0.3088 (2)0.0761 (10)
O40.2729 (3)0.0158 (3)0.3005 (2)0.0783 (10)
O50.1176 (3)0.0145 (3)0.1700 (2)0.0696 (9)
O60.3608 (2)0.9783 (2)0.98022 (16)0.0328 (5)
O70.5374 (4)0.9600 (3)0.8027 (2)0.0597 (7)
N10.0737 (3)0.3189 (3)0.49282 (19)0.0368 (7)
N20.3653 (2)0.6887 (2)0.88586 (17)0.0247 (5)
N30.6467 (3)0.7281 (3)0.93858 (18)0.0287 (6)
C10.2962 (3)0.5592 (3)0.5919 (2)0.0340 (7)
C20.4162 (4)0.6598 (4)0.6373 (2)0.0409 (8)
H20.40560.75290.65230.049*
C30.5468 (4)0.6234 (4)0.6594 (2)0.0425 (8)
H30.62370.69210.68920.051*
C40.5679 (4)0.4840 (4)0.6381 (2)0.0422 (8)
C50.4504 (4)0.3833 (4)0.5956 (2)0.0402 (8)
H50.46260.29040.58230.048*
C60.3151 (3)0.4164 (3)0.5722 (2)0.0333 (7)
C70.2007 (4)0.3062 (3)0.5261 (2)0.0373 (8)
H70.22100.21580.51960.045*
C80.0190 (4)0.1854 (3)0.4452 (2)0.0417 (9)
H8A0.11760.18270.46330.050*
H8B0.01730.10690.46740.050*
C90.0185 (4)0.1730 (3)0.3351 (2)0.0413 (8)
H9A0.08070.17780.31770.050*
H9B0.05540.25140.31340.050*
C100.7091 (4)0.4378 (5)0.6554 (3)0.0637 (12)
H100.71210.34280.64060.076*
C110.2257 (3)0.6732 (3)0.8551 (2)0.0300 (7)
H110.18090.75150.86220.036*
C120.1432 (3)0.5435 (3)0.8126 (2)0.0338 (7)
H120.04620.53720.79040.041*
C130.2056 (3)0.4265 (3)0.8038 (2)0.0337 (7)
H130.15120.34000.77620.040*
C140.3528 (3)0.4380 (3)0.8367 (2)0.0283 (7)
C150.4301 (4)0.3234 (3)0.8314 (2)0.0354 (7)
H150.38080.23350.80700.043*
C160.5725 (4)0.3427 (3)0.8609 (2)0.0354 (7)
H160.61920.26570.85740.043*
C170.6538 (3)0.4795 (3)0.8975 (2)0.0300 (7)
C180.8029 (4)0.5083 (4)0.9254 (2)0.0377 (8)
H180.85670.43630.92140.045*
C190.8693 (3)0.6443 (4)0.9590 (3)0.0409 (8)
H190.96850.66460.97790.049*
C200.7883 (3)0.7515 (3)0.9648 (2)0.0365 (8)
H200.83500.84280.98800.044*
C210.5797 (3)0.5936 (3)0.9048 (2)0.0251 (6)
C220.4286 (3)0.5728 (3)0.87541 (19)0.0246 (6)
O80.3647 (5)1.0030 (5)0.5080 (3)0.1310 (16)
O90.1389 (5)0.8522 (4)1.0899 (4)0.0905 (11)
O100.7513 (7)1.0569 (10)0.6797 (5)0.191 (3)
H6O0.319 (4)0.998 (4)0.9321 (19)0.063 (14)*
H7OA0.461 (2)0.955 (5)0.770 (2)0.077 (16)*
H7OB0.608 (2)0.983 (5)0.773 (3)0.087 (19)*
H10A0.819 (4)1.118 (4)0.669 (4)0.072 (18)*
H9OA0.206 (5)0.894 (5)1.064 (4)0.13 (3)*
H9OB0.104 (7)0.908 (5)1.128 (5)0.20 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0383 (3)0.0288 (3)0.0330 (3)0.0021 (2)0.0139 (2)0.0012 (2)
Cu20.0232 (2)0.0223 (2)0.0325 (2)0.00353 (15)0.00451 (15)0.00607 (15)
S0.0504 (6)0.0257 (4)0.0558 (6)0.0049 (4)0.0226 (5)0.0081 (4)
O10.0406 (14)0.0366 (13)0.0573 (16)0.0055 (11)0.0174 (12)0.0116 (11)
O20.050 (2)0.132 (3)0.089 (3)0.006 (2)0.0070 (18)0.031 (2)
O30.099 (2)0.0272 (14)0.092 (2)0.0119 (15)0.0423 (19)0.0037 (14)
O40.0503 (18)0.0652 (19)0.102 (3)0.0062 (15)0.0158 (17)0.0184 (17)
O50.096 (2)0.0500 (16)0.0528 (18)0.0127 (16)0.0188 (16)0.0153 (13)
O60.0271 (12)0.0265 (11)0.0400 (14)0.0067 (9)0.0087 (10)0.0087 (10)
O70.0544 (18)0.0668 (19)0.0512 (17)0.0069 (16)0.0089 (16)0.0138 (14)
N10.0446 (17)0.0280 (14)0.0319 (15)0.0017 (12)0.0140 (12)0.0018 (11)
N20.0227 (12)0.0243 (12)0.0259 (13)0.0049 (10)0.0009 (10)0.0001 (10)
N30.0266 (13)0.0280 (13)0.0300 (14)0.0054 (11)0.0006 (11)0.0007 (11)
C10.0352 (18)0.0385 (18)0.0244 (16)0.0022 (15)0.0019 (13)0.0018 (13)
C20.042 (2)0.0404 (19)0.0331 (18)0.0008 (16)0.0015 (15)0.0082 (15)
C30.0331 (18)0.058 (2)0.0293 (18)0.0042 (16)0.0022 (14)0.0009 (16)
C40.0368 (19)0.065 (2)0.0262 (17)0.0086 (17)0.0024 (14)0.0113 (16)
C50.046 (2)0.045 (2)0.0316 (18)0.0128 (16)0.0022 (15)0.0060 (15)
C60.0379 (18)0.0377 (18)0.0230 (16)0.0057 (14)0.0015 (13)0.0029 (13)
C70.050 (2)0.0301 (17)0.0306 (17)0.0068 (15)0.0064 (15)0.0047 (13)
C80.056 (2)0.0238 (16)0.0392 (19)0.0015 (15)0.0232 (16)0.0049 (14)
C90.049 (2)0.0272 (17)0.042 (2)0.0002 (15)0.0143 (16)0.0005 (14)
C100.042 (2)0.098 (4)0.046 (2)0.008 (2)0.0011 (19)0.020 (2)
C110.0270 (16)0.0320 (16)0.0295 (16)0.0069 (13)0.0014 (13)0.0009 (13)
C120.0249 (16)0.0404 (18)0.0316 (17)0.0006 (14)0.0037 (13)0.0002 (14)
C130.0343 (17)0.0281 (16)0.0326 (17)0.0028 (14)0.0016 (14)0.0041 (13)
C140.0329 (17)0.0248 (15)0.0251 (15)0.0012 (13)0.0021 (13)0.0017 (12)
C150.048 (2)0.0205 (15)0.0346 (18)0.0027 (14)0.0007 (15)0.0011 (13)
C160.048 (2)0.0253 (16)0.0358 (18)0.0139 (14)0.0049 (15)0.0042 (13)
C170.0345 (17)0.0309 (16)0.0261 (16)0.0093 (14)0.0029 (13)0.0051 (13)
C180.0388 (19)0.0426 (19)0.0364 (18)0.0216 (16)0.0016 (15)0.0053 (15)
C190.0241 (17)0.051 (2)0.049 (2)0.0115 (15)0.0022 (15)0.0069 (17)
C200.0245 (16)0.0375 (18)0.044 (2)0.0012 (14)0.0019 (14)0.0010 (15)
C210.0277 (15)0.0258 (15)0.0212 (14)0.0056 (12)0.0005 (12)0.0010 (12)
C220.0275 (15)0.0250 (15)0.0193 (14)0.0030 (12)0.0012 (12)0.0008 (11)
O80.115 (3)0.143 (4)0.135 (4)0.015 (3)0.015 (3)0.029 (3)
O90.075 (3)0.081 (2)0.110 (3)0.002 (2)0.023 (2)0.010 (2)
O100.131 (5)0.334 (10)0.144 (5)0.101 (6)0.047 (4)0.078 (6)
Geometric parameters (Å, º) top
Cu1—O11.894 (2)C6—C71.434 (4)
Cu1—N12.001 (3)C7—H70.9300
Cu2—O6i1.939 (2)C8—C91.514 (5)
Cu2—O61.950 (2)C8—H8A0.9700
Cu2—N32.014 (2)C8—H8B0.9700
Cu2—N22.016 (2)C9—H9A0.9700
Cu2—O72.326 (3)C9—H9B0.9700
Cu2—Cu2i2.9070 (10)C10—H100.9300
S—O31.438 (3)C11—C121.401 (4)
S—O51.445 (3)C11—H110.9300
S—O41.451 (3)C12—C131.365 (4)
S—C91.780 (3)C12—H120.9300
O1—C11.294 (4)C13—C141.406 (4)
O2—C101.171 (5)C13—H130.9300
O6—Cu2i1.939 (2)C14—C221.406 (4)
O6—H6O0.82 (3)C14—C151.430 (4)
O7—H7OA0.82 (3)C15—C161.345 (5)
O7—H7OB0.82 (3)C15—H150.9300
N1—C71.281 (4)C16—C171.432 (4)
N1—C81.485 (4)C16—H160.9300
N2—C111.327 (4)C17—C181.397 (4)
N2—C221.361 (4)C17—C211.407 (4)
N3—C201.326 (4)C18—C191.375 (5)
N3—C211.365 (4)C18—H180.9300
C1—C21.413 (4)C19—C201.392 (4)
C1—C61.429 (4)C19—H190.9300
C2—C31.359 (5)C20—H200.9300
C2—H20.9300C21—C221.421 (4)
C3—C41.405 (5)O8—O8ii2.568 (9)
C3—H30.9300O8—O4iii2.862 (6)
C4—C51.387 (5)O9—H9OA0.82 (5)
C4—C101.485 (5)O9—H9OB0.83 (6)
C5—C61.391 (5)O10—O8ii2.702 (8)
C5—H50.9300O10—H10A0.83 (4)
O1iii—Cu1—N1iii91.46 (10)N1—C7—C6127.0 (3)
O1—Cu1—N1iii88.54 (10)N1—C7—H7116.5
O1—Cu1—N191.46 (10)C6—C7—H7116.5
O6i—Cu2—O683.25 (9)N1—C8—C9110.1 (3)
O6i—Cu2—N396.57 (9)N1—C8—H8A109.6
O6—Cu2—N3166.94 (10)C9—C8—H8A109.6
O6i—Cu2—N2172.26 (10)N1—C8—H8B109.6
O6—Cu2—N296.57 (9)C9—C8—H8B109.6
N3—Cu2—N281.86 (10)H8A—C8—H8B108.2
O6i—Cu2—O790.62 (11)C8—C9—S112.2 (2)
O6—Cu2—O790.65 (12)C8—C9—H9A109.2
N3—Cu2—O7102.41 (12)S—C9—H9A109.2
N2—Cu2—O797.12 (10)C8—C9—H9B109.2
O6i—Cu2—Cu2i41.76 (6)S—C9—H9B109.2
O6—Cu2—Cu2i41.49 (6)H9A—C9—H9B107.9
N3—Cu2—Cu2i136.85 (7)O2—C10—C4123.7 (5)
N2—Cu2—Cu2i137.54 (7)O2—C10—H10118.1
O7—Cu2—Cu2i90.85 (9)C4—C10—H10118.1
O3—S—O5113.36 (19)N2—C11—C12122.6 (3)
O3—S—O4112.0 (2)N2—C11—H11118.7
O5—S—O4111.29 (19)C12—C11—H11118.7
O3—S—C9106.62 (16)C13—C12—C11119.8 (3)
O5—S—C9107.00 (17)C13—C12—H12120.1
O4—S—C9106.07 (18)C11—C12—H12120.1
C1—O1—Cu1130.9 (2)C12—C13—C14119.5 (3)
Cu2i—O6—Cu296.75 (9)C12—C13—H13120.3
Cu2i—O6—H6O113 (3)C14—C13—H13120.3
Cu2—O6—H6O112 (3)C13—C14—C22116.9 (3)
Cu2—O7—H7OA113 (3)C13—C14—C15124.7 (3)
Cu2—O7—H7OB134 (3)C22—C14—C15118.4 (3)
H7OA—O7—H7OB112.4 (18)C16—C15—C14121.5 (3)
C7—N1—C8114.4 (3)C16—C15—H15119.2
C7—N1—Cu1124.8 (2)C14—C15—H15119.2
C8—N1—Cu1120.8 (2)C15—C16—C17121.4 (3)
C11—N2—C22117.8 (2)C15—C16—H16119.3
C11—N2—Cu2129.7 (2)C17—C16—H16119.3
C22—N2—Cu2112.50 (18)C18—C17—C21117.3 (3)
C20—N3—C21118.1 (3)C18—C17—C16124.5 (3)
C20—N3—Cu2129.5 (2)C21—C17—C16118.2 (3)
C21—N3—Cu2112.34 (19)C19—C18—C17119.2 (3)
O1—C1—C2119.1 (3)C19—C18—H18120.4
O1—C1—C6123.0 (3)C17—C18—H18120.4
C2—C1—C6117.9 (3)C18—C19—C20120.1 (3)
C3—C2—C1121.4 (3)C18—C19—H19119.9
C3—C2—H2119.3C20—C19—H19119.9
C1—C2—H2119.3N3—C20—C19122.3 (3)
C2—C3—C4121.3 (3)N3—C20—H20118.9
C2—C3—H3119.4C19—C20—H20118.9
C4—C3—H3119.4N3—C21—C17123.0 (3)
C5—C4—C3118.1 (3)N3—C21—C22116.6 (3)
C5—C4—C10117.6 (4)C17—C21—C22120.4 (3)
C3—C4—C10124.3 (3)N2—C22—C14123.4 (3)
C4—C5—C6122.2 (3)N2—C22—C21116.6 (2)
C4—C5—H5118.9C14—C22—C21120.0 (3)
C6—C5—H5118.9O8ii—O8—O4iii115.0 (3)
C5—C6—C1119.0 (3)H9OA—O9—H9OB110 (5)
C5—C6—C7118.5 (3)O8ii—O10—H10A94 (4)
C1—C6—C7122.4 (3)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+1, y+2, z+1; (iii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6O···O5iii0.82 (3)2.26 (2)3.005 (4)152 (4)
O7—H7OA···O4iii0.82 (3)2.04 (4)2.844 (5)169 (5)
O7—H7OB···O100.82 (3)2.04 (4)2.841 (7)167 (4)
O9—H9OA···O60.82 (3)2.05 (5)2.868 (5)172 (6)
O9—H9OB···O5iv0.82 (3)2.54 (4)3.265 (6)148 (7)
O10—H10A···O3v0.83 (4)2.36 (5)2.903 (7)123 (5)
Symmetry codes: (iii) x, y+1, z+1; (iv) x, y+1, z+1; (v) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Cu2(OH)2(C12H8N2)2(H2O)2][Cu(C10H9NO5S)2]·6H2O
Mr1239.66
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.370 (2), 9.793 (2), 13.860 (4)
α, β, γ (°)98.02 (2), 93.61 (3), 99.63 (2)
V3)1236.8 (5)
Z1
Radiation typeMo Kα
µ (mm1)1.45
Crystal size (mm)0.48 × 0.38 × 0.34
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.531, 0.611
No. of measured, independent and
observed [I > 2σ(I)] reflections
4950, 4476, 3411
Rint0.011
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.092, 1.07
No. of reflections4476
No. of parameters364
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.61, 0.44

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL (Siemens, 1994), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
Cu1—O11.894 (2)Cu2—N32.014 (2)
Cu1—N12.001 (3)Cu2—N22.016 (2)
Cu2—O6i1.939 (2)Cu2—O72.326 (3)
Cu2—O61.950 (2)Cu2—Cu2i2.9070 (10)
O1ii—Cu1—N1ii91.46 (10)O6i—Cu2—N396.57 (9)
O1—Cu1—N1ii88.54 (10)O6—Cu2—N3166.94 (10)
O6i—Cu2—O683.25 (9)O6i—Cu2—N2172.26 (10)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6O···O5ii0.82 (3)2.26 (2)3.005 (4)152 (4)
O7—H7OA···O4ii0.82 (3)2.04 (4)2.844 (5)169 (5)
O7—H7OB···O100.82 (3)2.04 (4)2.841 (7)167 (4)
O9—H9OA···O60.82 (3)2.05 (5)2.868 (5)172 (6)
O9—H9OB···O5iii0.82 (3)2.54 (4)3.265 (6)148 (7)
O10—H10A···O3iv0.83 (4)2.36 (5)2.903 (7)123 (5)
Symmetry codes: (ii) x, y+1, z+1; (iii) x, y+1, z+1; (iv) x+1, y+1, z+1.
 

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